data_global _audit_creation_date "14-10-07" _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title '257ep70 in P 21 21 21' _chemical_name_systematic ? _chemical_melting_point ? #looking for refcif # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. ; _publ_contact_author_name 'Anthony Other' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_phone '+44 1865 000000' _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_email 'a.n.other@chem.no.ac.uk' _publ_requested_journal 'Section E' _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_section_title # Title of paper - generally just the systematic or trivial name ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Other, Anthony N.' # Author 1 ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Else, S. O.' # Author 2 ; ? # Address 2 ; ; ? # Footnote 2 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints (Cooper et al, 2010). Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.8540(10) _cell_length_b 14.840(2) _cell_length_c 18.005(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2365.7(5) _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,-y+1/2,-z' '-x,y+1/2,-z+1/2' '-x+1/2,-y,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C24.50 H17.50 F5.25 N1.75 O3.50 P1.75 S1.75 # Dc = 1.69 Fooo = 976.00 Mu = 3.99 M = 602.48 # Found Formula = C21 H30 F3 N2 O2 P1 S1 # Dc = 1.30 FOOO = 976.00 Mu = 2.47 M = 462.51 _chemical_formula_sum 'C21 H30 F3 N2 O2 P1 S1' _chemical_formula_moiety 'C15 H14 F3 N O2 P S, C6 H16 N' _chemical_compound_source ? _chemical_formula_weight 462.51 _cell_measurement_reflns_used 5662 _cell_measurement_theta_min 3.7400 _cell_measurement_theta_max 28.3840 _cell_measurement_temperature 200 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_min 0.214 _exptl_crystal_size_mid 0.262 _exptl_crystal_size_max 0.426 _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.247 # Sheldrick geometric approximatio 0.94 0.95 _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_correction_type 'analytical' _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_probe 'x-ray' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Atlas' _diffrn_detector_area_resol_mean 10.4685 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 21076 _reflns_number_total 5703 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections without Friedels Law is 5703 # Number of reflections with Friedels Law is 2093 # Theoretical number of reflections is about 3292 _diffrn_reflns_theta_min 2.908 _diffrn_reflns_theta_max 29.485 _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 26.703 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.60 _oxford_diffrn_Wilson_scale 0.05 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.54 _refine_diff_density_max 0.44 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 5692 _refine_ls_number_restraints 0 _refine_ls_number_parameters 273 _oxford_refine_ls_R_factor_ref 0.0601 _refine_ls_wR_factor_ref 0.0803 _refine_ls_goodness_of_fit_ref 0.9875 _refine_ls_shift/su_max 0.0002502 _refine_ls_shift/su_mean 0.0000166 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5692 _refine_ls_R_factor_all 0.0601 _refine_ls_wR_factor_all 0.0803 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4673 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_gt 0.0652 _refine_ls_abs_structure_Flack 0.05(9) _refine_ls_abs_structure_details 'Flack (1983), 3610 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration 'ad' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.101E+04 0.123E+04 718. 141. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2006). Gemini User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S -0.00549(9) 0.35955(4) 0.15959(4) 0.0287 1.0000 Uani . . . . . . O2 O -0.1045(2) 0.31071(13) 0.11070(11) 0.0346 1.0000 Uani . . . . . . O3 O -0.0723(3) 0.42830(14) 0.20491(12) 0.0454 1.0000 Uani . . . . . . N4 N 0.1035(3) 0.29414(15) 0.19894(12) 0.0281 1.0000 Uani . . . . . . P5 P 0.21365(9) 0.33619(5) 0.27016(4) 0.0295 1.0000 Uani . . . . . . C6 C 0.3338(3) 0.23562(18) 0.28389(15) 0.0289 1.0000 Uani . . . . . . C7 C 0.2689(4) 0.15436(19) 0.30795(14) 0.0338 1.0000 Uani . . . . . . C8 C 0.3540(4) 0.0772(2) 0.31704(16) 0.0403 1.0000 Uani . . . . . . C9 C 0.5071(4) 0.0812(2) 0.30372(18) 0.0481 1.0000 Uani . . . . . . C10 C 0.5729(4) 0.1605(2) 0.28114(19) 0.0489 1.0000 Uani . . . . . . C11 C 0.4882(4) 0.2394(2) 0.27049(17) 0.0385 1.0000 Uani . . . . . . C12 C 0.5659(4) 0.3240(3) 0.2448(2) 0.0600 1.0000 Uani . . . . . . H121 H 0.6547 0.3090 0.2154 0.0906 1.0000 Uiso R . . . . . H123 H 0.4972 0.3606 0.2154 0.0900 1.0000 Uiso R . . . . . H122 H 0.5988 0.3606 0.2861 0.0905 1.0000 Uiso R . . . . . H101 H 0.6749 0.1625 0.2723 0.0599 1.0000 Uiso R . . . . . H91 H 0.5673 0.0287 0.3098 0.0582 1.0000 Uiso R . . . . . H81 H 0.3096 0.0226 0.3316 0.0480 1.0000 Uiso R . . . . . H71 H 0.1667 0.1523 0.3193 0.0411 1.0000 Uiso R . . . . . C13 C 0.0951(4) 0.32538(19) 0.35355(15) 0.0348 1.0000 Uani . . . . . . C14 C -0.0534(4) 0.2974(2) 0.35077(18) 0.0428 1.0000 Uani . . . . . . C15 C -0.1443(5) 0.2963(3) 0.4138(2) 0.0628 1.0000 Uani . . . . . . C16 C -0.0830(7) 0.3238(3) 0.4804(2) 0.0752 1.0000 Uani . . . . . . C17 C 0.0637(6) 0.3508(3) 0.48445(19) 0.0672 1.0000 Uani . . . . . . C18 C 0.1578(5) 0.3534(2) 0.42202(17) 0.0490 1.0000 Uani . . . . . . C19 C 0.3171(5) 0.3837(3) 0.4283(2) 0.0663 1.0000 Uani . . . . . . H191 H 0.3384 0.4037 0.4770 0.0995 1.0000 Uiso R . . . . . H193 H 0.3360 0.4333 0.3955 0.0983 1.0000 Uiso R . . . . . H192 H 0.3847 0.3367 0.4154 0.0989 1.0000 Uiso R . . . . . H171 H 0.1034 0.3700 0.5292 0.0810 1.0000 Uiso R . . . . . H161 H -0.1423 0.3250 0.5226 0.0901 1.0000 Uiso R . . . . . H151 H -0.2465 0.2765 0.4116 0.0759 1.0000 Uiso R . . . . . H141 H -0.0962 0.2777 0.3061 0.0508 1.0000 Uiso R . . . . . C20 C 0.1050(4) 0.4266(2) 0.09282(18) 0.0425 1.0000 Uani . . . . . . F21 F 0.0128(3) 0.47537(14) 0.04978(11) 0.0648 1.0000 Uani . . . . . . F22 F 0.1969(3) 0.48425(15) 0.12608(12) 0.0740 1.0000 Uani . . . . . . F23 F 0.1884(3) 0.37562(16) 0.04823(12) 0.0678 1.0000 Uani . . . . . . N24 N 0.8469(3) 0.62868(16) 0.38889(13) 0.0333 1.0000 Uani . . . . . . C25 C 0.9034(4) 0.6533(2) 0.46527(15) 0.0394 1.0000 Uani . . . . . . C26 C 0.8965(5) 0.5774(2) 0.52100(16) 0.0482 1.0000 Uani . . . . . . H261 H 0.9290 0.6009 0.5678 0.0725 1.0000 Uiso R . . . . . H263 H 0.7917 0.5539 0.5244 0.0722 1.0000 Uiso R . . . . . H262 H 0.9627 0.5286 0.5065 0.0721 1.0000 Uiso R . . . . . H252 H 0.8407 0.7039 0.4834 0.0469 1.0000 Uiso R . . . . . H251 H 1.0063 0.6752 0.4599 0.0470 1.0000 Uiso R . . . . . C27 C 0.9377(4) 0.5554(2) 0.35267(17) 0.0423 1.0000 Uani . . . . . . C28 C 1.1007(5) 0.5808(2) 0.3429(3) 0.0667 1.0000 Uani . . . . . . H281 H 1.1517 0.5342 0.3142 0.0997 1.0000 Uiso R . . . . . H282 H 1.1505 0.5846 0.3904 0.0999 1.0000 Uiso R . . . . . H283 H 1.1143 0.6376 0.3185 0.0996 1.0000 Uiso R . . . . . H271 H 0.9307 0.5004 0.3821 0.0500 1.0000 Uiso R . . . . . H272 H 0.8907 0.5421 0.3063 0.0508 1.0000 Uiso R . . . . . C29 C 0.6827(4) 0.6047(2) 0.38743(17) 0.0429 1.0000 Uani . . . . . . C30 C 0.5825(4) 0.6797(3) 0.41530(19) 0.0569 1.0000 Uani . . . . . . H301 H 0.4775 0.6663 0.4054 0.0850 1.0000 Uiso R . . . . . H303 H 0.5970 0.6873 0.4676 0.0849 1.0000 Uiso R . . . . . H302 H 0.6102 0.7369 0.3911 0.0841 1.0000 Uiso R . . . . . H291 H 0.6702 0.5494 0.4172 0.0499 1.0000 Uiso R . . . . . H292 H 0.6565 0.5917 0.3360 0.0517 1.0000 Uiso R . . . . . H241 H 0.8552 0.6790 0.3620 0.0492 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0334(3) 0.0263(3) 0.0265(3) 0.0015(3) -0.0033(3) 0.0007(3) O2 0.0340(11) 0.0371(11) 0.0327(10) 0.0022(9) -0.0076(9) -0.0039(9) O3 0.0591(15) 0.0370(12) 0.0402(12) -0.0051(10) -0.0055(11) 0.0182(11) N4 0.0316(12) 0.0265(11) 0.0263(11) 0.0001(9) -0.0003(10) 0.0018(10) P5 0.0356(4) 0.0247(3) 0.0282(3) 0.0001(3) -0.0053(3) -0.0006(3) C6 0.0297(14) 0.0312(14) 0.0258(14) 0.0010(11) -0.0073(11) 0.0038(11) C7 0.0396(16) 0.0334(15) 0.0286(13) 0.0003(12) -0.0038(12) -0.0006(13) C8 0.056(2) 0.0320(15) 0.0326(16) 0.0046(12) -0.0099(14) 0.0004(15) C9 0.050(2) 0.0406(17) 0.0534(19) -0.0032(15) -0.0179(18) 0.0128(17) C10 0.0365(17) 0.053(2) 0.057(2) -0.0038(18) -0.0060(16) 0.0054(16) C11 0.0363(16) 0.0418(16) 0.0375(15) -0.0006(13) -0.0047(15) -0.0031(14) C12 0.0423(19) 0.060(2) 0.077(3) 0.013(2) 0.0008(18) -0.0095(18) C13 0.0504(18) 0.0253(14) 0.0286(14) -0.0019(11) 0.0003(13) 0.0085(13) C14 0.055(2) 0.0382(17) 0.0355(17) 0.0030(14) 0.0126(15) 0.0041(15) C15 0.082(3) 0.051(2) 0.055(2) 0.0103(19) 0.032(2) 0.007(2) C16 0.129(4) 0.059(3) 0.038(2) 0.0100(19) 0.035(3) 0.026(3) C17 0.130(4) 0.048(2) 0.0243(16) -0.0058(15) -0.002(2) 0.031(3) C18 0.085(3) 0.0331(17) 0.0293(16) -0.0080(13) -0.0121(16) 0.0170(18) C19 0.092(3) 0.054(2) 0.053(2) -0.0173(18) -0.039(2) 0.003(2) C20 0.0476(19) 0.0379(17) 0.0419(18) 0.0109(14) -0.0132(15) -0.0123(15) F21 0.0698(15) 0.0640(13) 0.0606(13) 0.0385(11) -0.0226(12) -0.0142(13) F22 0.0841(17) 0.0687(15) 0.0693(15) 0.0246(12) -0.0317(13) -0.0466(14) F23 0.0671(15) 0.0809(16) 0.0553(13) 0.0157(12) 0.0242(12) -0.0054(13) N24 0.0503(16) 0.0259(12) 0.0237(11) 0.0009(9) 0.0035(10) 0.0004(11) C25 0.0546(19) 0.0357(16) 0.0278(14) -0.0062(12) -0.0006(13) 0.0008(15) C26 0.066(2) 0.0482(19) 0.0301(16) 0.0042(14) -0.0006(16) 0.0039(18) C27 0.068(2) 0.0274(15) 0.0310(16) -0.0030(12) 0.0061(15) 0.0041(14) C28 0.067(3) 0.042(2) 0.092(3) -0.001(2) 0.030(3) 0.0085(19) C29 0.050(2) 0.0482(19) 0.0301(15) 0.0025(14) 0.0019(14) -0.0063(16) C30 0.053(2) 0.078(3) 0.0397(18) 0.0039(18) 0.0093(17) 0.012(2) _refine_ls_extinction_coef 170(10) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 5.58(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.438(2) yes S1 . O3 . 1.434(2) yes S1 . N4 . 1.541(2) yes S1 . C20 . 1.842(3) yes N4 . P5 . 1.728(2) yes P5 . C6 . 1.849(3) yes P5 . C13 . 1.839(3) yes C6 . C7 . 1.404(4) yes C6 . C11 . 1.389(4) yes C7 . C8 . 1.380(4) yes C7 . H71 . 0.928 no C8 . C9 . 1.378(5) yes C8 . H81 . 0.938 no C9 . C10 . 1.376(5) yes C9 . H91 . 0.950 no C10 . C11 . 1.403(4) yes C10 . H101 . 0.917 no C11 . C12 . 1.505(4) yes C12 . H121 . 0.973 no C12 . H123 . 0.972 no C12 . H122 . 0.966 no C13 . C14 . 1.379(4) yes C13 . C18 . 1.414(4) yes C14 . C15 . 1.392(4) yes C14 . H141 . 0.936 no C15 . C16 . 1.378(6) yes C15 . H151 . 0.952 no C16 . C17 . 1.362(6) yes C16 . H161 . 0.923 no C17 . C18 . 1.400(5) yes C17 . H171 . 0.925 no C18 . C19 . 1.485(5) yes C19 . H191 . 0.945 no C19 . H193 . 0.958 no C19 . H192 . 0.948 no C20 . F21 . 1.338(4) yes C20 . F22 . 1.324(4) yes C20 . F23 . 1.327(4) yes N24 . C25 . 1.508(3) yes N24 . C27 . 1.501(4) yes N24 . C29 . 1.497(4) yes N24 . H241 . 0.893 no C25 . C26 . 1.510(4) yes C25 . H252 . 0.989 no C25 . H251 . 0.973 no C26 . H261 . 0.956 no C26 . H263 . 0.992 no C26 . H262 . 0.968 no C27 . C28 . 1.501(5) yes C27 . H271 . 0.976 no C27 . H272 . 0.954 no C28 . H281 . 0.974 no C28 . H282 . 0.964 no C28 . H283 . 0.959 no C29 . C30 . 1.509(5) yes C29 . H291 . 0.986 no C29 . H292 . 0.974 no C30 . H301 . 0.968 no C30 . H303 . 0.957 no C30 . H302 . 0.985 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 117.10(14) yes O2 . S1 . N4 . 110.21(12) yes O3 . S1 . N4 . 116.41(12) yes O2 . S1 . C20 . 101.33(13) yes O3 . S1 . C20 . 101.89(15) yes N4 . S1 . C20 . 107.93(15) yes S1 . N4 . P5 . 117.85(14) yes N4 . P5 . C6 . 97.61(12) yes N4 . P5 . C13 . 104.61(13) yes C6 . P5 . C13 . 98.56(13) yes P5 . C6 . C7 . 119.9(2) yes P5 . C6 . C11 . 120.7(2) yes C7 . C6 . C11 . 119.4(3) yes C6 . C7 . C8 . 121.7(3) yes C6 . C7 . H71 . 119.6 no C8 . C7 . H71 . 118.6 no C7 . C8 . C9 . 118.7(3) yes C7 . C8 . H81 . 121.4 no C9 . C8 . H81 . 119.8 no C8 . C9 . C10 . 120.3(3) yes C8 . C9 . H91 . 119.8 no C10 . C9 . H91 . 119.9 no C9 . C10 . C11 . 121.8(3) yes C9 . C10 . H101 . 119.7 no C11 . C10 . H101 . 118.5 no C10 . C11 . C6 . 118.0(3) yes C10 . C11 . C12 . 119.5(3) yes C6 . C11 . C12 . 122.5(3) yes C11 . C12 . H121 . 110.2 no C11 . C12 . H123 . 110.3 no H121 . C12 . H123 . 109.8 no C11 . C12 . H122 . 111.7 no H121 . C12 . H122 . 107.7 no H123 . C12 . H122 . 107.1 no P5 . C13 . C14 . 122.7(2) yes P5 . C13 . C18 . 117.5(3) yes C14 . C13 . C18 . 119.6(3) yes C13 . C14 . C15 . 121.7(4) yes C13 . C14 . H141 . 120.7 no C15 . C14 . H141 . 117.6 no C14 . C15 . C16 . 118.6(4) yes C14 . C15 . H151 . 121.2 no C16 . C15 . H151 . 120.2 no C15 . C16 . C17 . 120.6(4) yes C15 . C16 . H161 . 119.9 no C17 . C16 . H161 . 119.5 no C16 . C17 . C18 . 122.2(4) yes C16 . C17 . H171 . 120.0 no C18 . C17 . H171 . 117.7 no C13 . C18 . C17 . 117.3(4) yes C13 . C18 . C19 . 121.8(3) yes C17 . C18 . C19 . 120.9(3) yes C18 . C19 . H191 . 110.8 no C18 . C19 . H193 . 110.6 no H191 . C19 . H193 . 107.2 no C18 . C19 . H192 . 111.0 no H191 . C19 . H192 . 109.3 no H193 . C19 . H192 . 107.8 no S1 . C20 . F21 . 110.2(2) yes S1 . C20 . F22 . 112.3(2) yes F21 . C20 . F22 . 106.7(3) yes S1 . C20 . F23 . 112.5(2) yes F21 . C20 . F23 . 107.3(3) yes F22 . C20 . F23 . 107.5(3) yes C25 . N24 . C27 . 113.2(2) yes C25 . N24 . C29 . 113.3(2) yes C27 . N24 . C29 . 109.9(2) yes C25 . N24 . H241 . 105.3 no C27 . N24 . H241 . 109.0 no C29 . N24 . H241 . 105.6 no N24 . C25 . C26 . 114.3(3) yes N24 . C25 . H252 . 107.4 no C26 . C25 . H252 . 109.0 no N24 . C25 . H251 . 107.5 no C26 . C25 . H251 . 110.8 no H252 . C25 . H251 . 107.7 no C25 . C26 . H261 . 107.5 no C25 . C26 . H263 . 109.9 no H261 . C26 . H263 . 110.9 no C25 . C26 . H262 . 110.8 no H261 . C26 . H262 . 109.1 no H263 . C26 . H262 . 108.7 no N24 . C27 . C28 . 112.6(3) yes N24 . C27 . H271 . 109.7 no C28 . C27 . H271 . 109.5 no N24 . C27 . H272 . 107.3 no C28 . C27 . H272 . 111.6 no H271 . C27 . H272 . 105.9 no C27 . C28 . H281 . 109.3 no C27 . C28 . H282 . 110.6 no H281 . C28 . H282 . 107.5 no C27 . C28 . H283 . 113.2 no H281 . C28 . H283 . 108.8 no H282 . C28 . H283 . 107.2 no N24 . C29 . C30 . 112.9(3) yes N24 . C29 . H291 . 107.3 no C30 . C29 . H291 . 111.5 no N24 . C29 . H292 . 107.2 no C30 . C29 . H292 . 108.8 no H291 . C29 . H292 . 109.0 no C29 . C30 . H301 . 110.6 no C29 . C30 . H303 . 109.6 no H301 . C30 . H303 . 109.5 no C29 . C30 . H302 . 110.0 no H301 . C30 . H302 . 109.5 no H303 . C30 . H302 . 107.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C25 . H251 . O2 3_655 129.64(9) 0.973 2.532 3.240(5) yes C27 . H272 . O3 1_655 136.08(9) 0.954 2.508 3.263(5) yes C30 . H303 . O2 4_565 171.25(10) 0.957 2.578 3.526(5) yes N24 . H241 . N4 3_655 174.49(10) 0.893 2.063 2.953(5) yes _iucr_refine_instruction_details_constraints ; # # Punched on 07/10/14 at 10:26:38 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM CONT ENANTIO RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 123,X'S) H ( 122,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 193,X'S) H ( 192,X'S) RIDE N ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 252,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) H ( 263,X'S) H ( 262,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) RIDE C ( 28,X'S) H ( 281,X'S) H ( 282,X'S) H ( 283,X'S) RIDE C ( 29,X'S) H ( 291,X'S) H ( 292,X'S) RIDE C ( 30,X'S) H ( 301,X'S) H ( 303,X'S) H ( 302,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 07/10/14 at 10:26:38 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;