#============================================================================== data_global #============================================================================== _publ_contact_author_name 'Darren J. Dixon' _publ_contact_author_address darren.dixon@chem.ox.ac.uk loop_ _publ_author_name _publ_author_address 'Alex W. Gregory' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Pavol Jakubec' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Paul Turner' ; AstraZeneca R&D, Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG. UK. ; 'Darren J. Dixon' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. darren.dixon@chem.ox.ac.uk ; _journal_name_full 'Angewandte Chemie International Edition' _journal_volume '.' _journal_page_first '.' _journal_page_last '.' _journal_year '2013' _ccdc_journal_depnumber '.' _publ_section_title ; Hydroamination and Enantioselective Bronsted Acid-Catalyzed N-Sulfonyliminium Cyclization Cascade ; _publ_section_abstract ; We have developed highly enantioselective N-sulfonyliminium cyclization cascade that allows access to complex sulfonamide scaffolds in excellent yield, which would be formidable targets through alternative routes. We have also proven that this tool can be used to create different backboned ring systems of various sizes with most cases providing excellent yields and enantiomeric excess. Mechanistic understanding has allowed us to control the background gold catalysed reaction. ; #============================================================================== data_10b #============================================================================== _audit_creation_date "2013-05-09" _audit_creation_method CRYSTALS_ver_14.52 _oxford_structure_analysis_title '015DJD12' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 11.0236(2) _cell_length_b 12.9544(2) _cell_length_c 13.4366(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1918.80(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,z+1/2' 'x+1/2,-y+1/2,-z' '-x,y+1/2,-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' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 '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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H17 Br1 Cl3 N2 O6 # Dc = 1.80 Fooo = 912.00 Mu = 25.98 M = 519.58 # Found Formula = C17 H18 Br1 Cl3 N2 O1 # Dc = 1.57 FOOO = 912.00 Mu = 25.67 M = 452.60 _chemical_formula_sum 'C17 H18 Br1 Cl3 N2 O1' _chemical_formula_moiety 'C16 H17 Br N2 O, C H Cl3' _chemical_compound_source . _chemical_formula_weight 452.60 _cell_measurement_reflns_used 83413 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.62 _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.567 # Sheldrick geometric approximatio 0.38 0.46 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.17 _exptl_absorpt_correction_T_max 0.46 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 150 _diffrn_reflns_number 56832 _reflns_number_total 4361 _diffrn_reflns_av_R_equivalents 0.087 # Number of reflections without Friedels Law is 4361 # Number of reflections with Friedels Law is 2468 # Theoretical number of reflections is about 2198 _diffrn_reflns_theta_min 5.159 _diffrn_reflns_theta_max 27.475 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.925 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 3.71 _oxford_diffrn_Wilson_scale 3.06 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.44 _refine_diff_density_max 0.42 # 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>-3.0\s(I) _refine_ls_number_reflns 4361 _refine_ls_number_restraints 162 _refine_ls_number_parameters 255 _oxford_refine_ls_R_factor_ref 0.0374 _refine_ls_wR_factor_ref 0.0832 _refine_ls_goodness_of_fit_ref 1.0001 _refine_ls_shift/su_max 0.0020766 _refine_ls_shift/su_mean 0.0001238 # The values computed with all filters except I/sigma _oxford_reflns_number_all 4361 _refine_ls_R_factor_all 0.0374 _refine_ls_wR_factor_all 0.0832 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4092 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_gt 0.0808 _refine_ls_abs_structure_Flack -0.007(8) _refine_ls_abs_structure_details 'Flack (1983), 1893 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: 69.2 115. 71.6 31.4 7.79 ; # Insert your own references if required - in alphabetical order _publ_section_references ; 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. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. 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 Br1 Br 0.65201(3) 0.67046(3) 1.08633(3) 0.0538 1.0000 Uani . . . . . . C2 C 0.6812(2) 0.65084(19) 0.9491(2) 0.0375 1.0000 Uani . . . . . . C3 C 0.5948(2) 0.60131(18) 0.89063(19) 0.0304 1.0000 Uani . . . . . . N4 N 0.48228(17) 0.56306(15) 0.91457(17) 0.0289 1.0000 Uani . . . . . . C5 C 0.4336(2) 0.51801(19) 0.82999(17) 0.0269 1.0000 Uani . . . . . . C6 C 0.5127(2) 0.52769(19) 0.75153(19) 0.0299 1.0000 Uani . . . . . . C7 C 0.6164(2) 0.58180(19) 0.78843(19) 0.0321 1.0000 Uani . . . . . . C8 C 0.7263(2) 0.6159(2) 0.7450(2) 0.0424 1.0000 Uani . . . . . . C9 C 0.8085(3) 0.6668(3) 0.8039(3) 0.0480 1.0000 Uani . . . . . . C10 C 0.7884(2) 0.6833(2) 0.9055(3) 0.0454 1.0000 Uani . . . . . . C11 C 0.4861(3) 0.4819(2) 0.65142(19) 0.0377 1.0000 Uani . . . . . . C12 C 0.3845(3) 0.4028(2) 0.66363(19) 0.0366 1.0000 Uani . . . . . . N13 N 0.28353(19) 0.44722(18) 0.72179(15) 0.0318 1.0000 Uani . . . . . . C14 C 0.3093(2) 0.47060(19) 0.82822(17) 0.0274 1.0000 Uani . . . . . . C15 C 0.3064(3) 0.3708(2) 0.88971(19) 0.0361 1.0000 Uani . . . . . . C16 C 0.2171(2) 0.5493(2) 0.8680(2) 0.0348 1.0000 Uani . . . . . . C17 C 0.0883(3) 0.5161(3) 0.8449(2) 0.0433 1.0000 Uani . . . . . . C18 C 0.0731(3) 0.5135(3) 0.7325(2) 0.0475 1.0000 Uani . . . . . . C19 C 0.1766(2) 0.4651(2) 0.6760(2) 0.0360 1.0000 Uani . . . . . . O20 O 0.16200(19) 0.44316(18) 0.58674(15) 0.0457 1.0000 Uani . . . . . . C21 C 0.6761(2) 0.3428(2) 0.9014(2) 0.0530 0.739(8) Uani D . P 1 1 . Cl22 Cl 0.5983(2) 0.3334(2) 1.01359(14) 0.0620 0.739(8) Uani D . P 1 1 . Cl23 Cl 0.6434(4) 0.2372(4) 0.8252(3) 0.0789 0.739(8) Uani D . P 1 1 . Cl24 Cl 0.83178(19) 0.3520(3) 0.9223(3) 0.1103 0.739(8) Uani D . P 1 1 . C25 C 0.7068(7) 0.3351(4) 0.8686(6) 0.0653 0.261(8) Uani D . P 1 2 . Cl26 Cl 0.6526(11) 0.3566(4) 0.9885(5) 0.0775 0.261(8) Uani D . P 1 2 . Cl27 Cl 0.6276(5) 0.2345(8) 0.8120(6) 0.0449 0.261(8) Uani D . P 1 2 . Cl28 Cl 0.8619(7) 0.3086(6) 0.8709(8) 0.0923 0.261(8) Uani D . P 1 2 . H81 H 0.7411 0.6060 0.6779 0.0511 1.0000 Uiso R . . . . . H91 H 0.8809 0.6888 0.7744 0.0580 1.0000 Uiso R . . . . . H101 H 0.8460 0.7155 0.9432 0.0539 1.0000 Uiso R . . . . . H111 H 0.5574 0.4481 0.6240 0.0450 1.0000 Uiso R . . . . . H112 H 0.4596 0.5355 0.6043 0.0454 1.0000 Uiso R . . . . . H121 H 0.4164 0.3434 0.7000 0.0432 1.0000 Uiso R . . . . . H122 H 0.3531 0.3786 0.6004 0.0436 1.0000 Uiso R . . . . . H151 H 0.2278 0.3397 0.8850 0.0533 1.0000 Uiso R . . . . . H152 H 0.3263 0.3876 0.9579 0.0534 1.0000 Uiso R . . . . . H153 H 0.3649 0.3239 0.8652 0.0533 1.0000 Uiso R . . . . . H161 H 0.2277 0.5547 0.9386 0.0418 1.0000 Uiso R . . . . . H162 H 0.2337 0.6164 0.8380 0.0419 1.0000 Uiso R . . . . . H171 H 0.0313 0.5647 0.8702 0.0517 1.0000 Uiso R . . . . . H172 H 0.0713 0.4491 0.8731 0.0517 1.0000 Uiso R . . . . . H181 H 0.0687 0.5825 0.7066 0.0583 1.0000 Uiso R . . . . . H182 H 0.0010 0.4749 0.7145 0.0575 1.0000 Uiso R . . . . . H211 H 0.6492 0.4053 0.8682 0.0639 0.739(8) Uiso R . P 1 1 . H251 H 0.6951 0.3976 0.8291 0.0778 0.261(8) Uiso R . P 1 2 . H41 H 0.4494 0.5652 0.9709 0.0352 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 Br1 0.05236(17) 0.05674(18) 0.05220(17) -0.01813(14) -0.00665(15) -0.01281(15) C2 0.0338(13) 0.0294(12) 0.0493(14) -0.0007(10) -0.0014(10) -0.0009(9) C3 0.0248(10) 0.0280(11) 0.0384(13) 0.0030(9) 0.0029(9) 0.0008(8) N4 0.0265(9) 0.0308(9) 0.0296(9) 0.0000(8) 0.0008(8) -0.0035(7) C5 0.0273(11) 0.0266(10) 0.0268(11) 0.0009(8) 0.0003(9) 0.0007(9) C6 0.0280(11) 0.0317(11) 0.0300(11) 0.0034(9) 0.0047(9) 0.0023(9) C7 0.0298(12) 0.0283(11) 0.0383(12) 0.0066(9) 0.0069(9) 0.0008(9) C8 0.0327(13) 0.0425(15) 0.0519(16) 0.0144(13) 0.0126(12) 0.0041(11) C9 0.0264(12) 0.0435(14) 0.074(2) 0.0162(15) 0.0071(12) -0.0011(12) C10 0.0295(12) 0.0356(13) 0.0710(19) 0.0032(15) -0.0010(14) -0.0050(10) C11 0.0330(13) 0.0502(15) 0.0299(12) -0.0006(11) 0.0059(10) 0.0037(11) C12 0.0365(13) 0.0437(14) 0.0297(11) -0.0064(10) -0.0013(10) 0.0059(10) N13 0.0276(10) 0.0424(11) 0.0256(9) -0.0006(8) -0.0018(8) 0.0032(8) C14 0.0255(11) 0.0329(11) 0.0239(10) 0.0000(8) -0.0005(8) -0.0003(9) C15 0.0358(12) 0.0379(12) 0.0345(13) 0.0052(10) -0.0042(10) -0.0085(10) C16 0.0262(12) 0.0447(14) 0.0335(12) -0.0025(11) 0.0023(10) 0.0011(10) C17 0.0260(13) 0.067(2) 0.0373(14) -0.0036(13) 0.0013(10) 0.0027(12) C18 0.0296(13) 0.073(2) 0.0398(14) -0.0062(14) -0.0048(11) 0.0070(13) C19 0.0314(13) 0.0475(14) 0.0291(12) 0.0027(10) -0.0041(10) 0.0015(10) O20 0.0391(10) 0.0690(12) 0.0290(8) -0.0025(9) -0.0072(9) 0.0048(9) C21 0.0506(19) 0.0427(18) 0.066(2) 0.0043(17) -0.0121(18) -0.0010(16) Cl22 0.0550(10) 0.0807(10) 0.0502(7) -0.0013(8) -0.0150(6) 0.0210(8) Cl23 0.089(2) 0.0648(14) 0.0833(17) -0.0288(13) 0.0082(15) -0.0014(16) Cl24 0.0523(9) 0.127(2) 0.151(3) 0.022(2) -0.0107(13) -0.0348(11) C25 0.071(4) 0.050(4) 0.075(4) -0.005(3) -0.030(4) -0.001(3) Cl26 0.111(5) 0.059(2) 0.063(3) -0.0177(19) -0.030(3) 0.019(3) Cl27 0.0318(19) 0.047(3) 0.056(3) -0.0139(19) -0.0096(16) 0.0025(14) Cl28 0.065(3) 0.081(3) 0.131(5) 0.014(3) -0.034(3) -0.026(2) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 0.6515(14) 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 Br1 . C2 . 1.889(3) yes C2 . C3 . 1.391(4) yes C2 . C10 . 1.384(4) yes C3 . N4 . 1.374(3) yes C3 . C7 . 1.416(4) yes N4 . C5 . 1.385(3) yes N4 . H41 . 0.840 no C5 . C6 . 1.374(3) yes C5 . C14 . 1.502(3) yes C6 . C7 . 1.429(4) yes C6 . C11 . 1.499(4) yes C7 . C8 . 1.415(4) yes C8 . C9 . 1.371(5) yes C8 . H81 . 0.926 no C9 . C10 . 1.399(5) yes C9 . H91 . 0.936 no C10 . H101 . 0.914 no C11 . C12 . 1.527(4) yes C11 . H111 . 0.972 no C11 . H112 . 0.984 no C12 . N13 . 1.477(3) yes C12 . H121 . 0.976 no C12 . H122 . 0.968 no N13 . C14 . 1.489(3) yes N13 . C19 . 1.349(3) yes C14 . C15 . 1.534(3) yes C14 . C16 . 1.536(3) yes C15 . H151 . 0.958 no C15 . H152 . 0.967 no C15 . H153 . 0.945 no C16 . C17 . 1.516(4) yes C16 . H161 . 0.957 no C16 . H162 . 0.977 no C17 . C18 . 1.520(4) yes C17 . H171 . 0.952 no C17 . H172 . 0.966 no C18 . C19 . 1.507(4) yes C18 . H181 . 0.961 no C18 . H182 . 0.969 no C19 . O20 . 1.244(3) yes C21 . Cl22 . 1.738(3) yes C21 . Cl23 . 1.746(3) yes C21 . Cl24 . 1.743(3) yes C21 . H211 . 0.972 no C25 . Cl26 . 1.740(5) yes C25 . Cl27 . 1.743(5) yes C25 . Cl28 . 1.744(5) yes C25 . H251 . 0.976 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 Br1 . C2 . C3 . 119.8(2) yes Br1 . C2 . C10 . 121.2(2) yes C3 . C2 . C10 . 119.0(3) yes C2 . C3 . N4 . 130.7(2) yes C2 . C3 . C7 . 121.0(2) yes N4 . C3 . C7 . 108.3(2) yes C3 . N4 . C5 . 108.0(2) yes C3 . N4 . H41 . 126.0 no C5 . N4 . H41 . 125.9 no N4 . C5 . C6 . 110.2(2) yes N4 . C5 . C14 . 122.6(2) yes C6 . C5 . C14 . 127.2(2) yes C5 . C6 . C7 . 106.6(2) yes C5 . C6 . C11 . 121.9(2) yes C7 . C6 . C11 . 131.5(2) yes C6 . C7 . C3 . 106.8(2) yes C6 . C7 . C8 . 134.0(3) yes C3 . C7 . C8 . 119.2(3) yes C7 . C8 . C9 . 118.5(3) yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 120.8 no C8 . C9 . C10 . 122.1(3) yes C8 . C9 . H91 . 117.7 no C10 . C9 . H91 . 120.1 no C9 . C10 . C2 . 120.1(3) yes C9 . C10 . H101 . 120.0 no C2 . C10 . H101 . 119.8 no C6 . C11 . C12 . 108.2(2) yes C6 . C11 . H111 . 111.1 no C12 . C11 . H111 . 109.4 no C6 . C11 . H112 . 110.9 no C12 . C11 . H112 . 109.0 no H111 . C11 . H112 . 108.2 no C11 . C12 . N13 . 110.4(2) yes C11 . C12 . H121 . 108.5 no N13 . C12 . H121 . 108.3 no C11 . C12 . H122 . 112.6 no N13 . C12 . H122 . 108.7 no H121 . C12 . H122 . 108.3 no C12 . N13 . C14 . 116.3(2) yes C12 . N13 . C19 . 119.0(2) yes C14 . N13 . C19 . 124.7(2) yes C5 . C14 . N13 . 105.81(19) yes C5 . C14 . C15 . 110.8(2) yes N13 . C14 . C15 . 110.0(2) yes C5 . C14 . C16 . 109.1(2) yes N13 . C14 . C16 . 110.1(2) yes C15 . C14 . C16 . 111.0(2) yes C14 . C15 . H151 . 109.7 no C14 . C15 . H152 . 108.4 no H151 . C15 . H152 . 111.2 no C14 . C15 . H153 . 109.9 no H151 . C15 . H153 . 108.9 no H152 . C15 . H153 . 108.7 no C14 . C16 . C17 . 111.1(2) yes C14 . C16 . H161 . 108.2 no C17 . C16 . H161 . 109.8 no C14 . C16 . H162 . 108.8 no C17 . C16 . H162 . 110.1 no H161 . C16 . H162 . 108.7 no C16 . C17 . C18 . 108.3(2) yes C16 . C17 . H171 . 110.9 no C18 . C17 . H171 . 107.3 no C16 . C17 . H172 . 110.8 no C18 . C17 . H172 . 110.4 no H171 . C17 . H172 . 109.0 no C17 . C18 . C19 . 115.2(2) yes C17 . C18 . H181 . 110.1 no C19 . C18 . H181 . 104.1 no C17 . C18 . H182 . 110.5 no C19 . C18 . H182 . 106.4 no H181 . C18 . H182 . 110.4 no C18 . C19 . N13 . 120.3(2) yes C18 . C19 . O20 . 118.8(2) yes N13 . C19 . O20 . 120.9(3) yes Cl22 . C21 . Cl23 . 110.61(6) yes Cl22 . C21 . Cl24 . 110.54(6) yes Cl23 . C21 . Cl24 . 110.61(6) yes Cl22 . C21 . H211 . 107.9 no Cl23 . C21 . H211 . 108.7 no Cl24 . C21 . H211 . 108.5 no Cl26 . C25 . Cl27 . 110.58(6) yes Cl26 . C25 . Cl28 . 110.60(6) yes Cl27 . C25 . Cl28 . 110.59(6) yes Cl26 . C25 . H251 . 108.9 no Cl27 . C25 . H251 . 108.4 no Cl28 . C25 . H251 . 107.6 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 C16 . H161 . O20 2_565 155.41(8) 0.957 2.333 3.229(4) yes C21 . H211 . C7 . 169.72(8) 0.972 2.550 3.511(4) yes C25 . H211 . C7 . 144.9(5) 1.109 2.550 3.517(4) yes C25 . H251 . C7 . 157.0(2) 0.976 2.597 3.517(4) yes N4 . H41 . O20 2_565 166.32(9) 0.840 1.985 2.809(4) yes _iucr_refine_instructions_details_constraints ; # # Punched on 09/05/13 at 21:14:30 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO EQUIV PART(1001,OCC) PART(1002,OCC) WEIGHT -1 PART(1002,OCC) RIDE N ( 4,X'S) H ( 41,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 ( 11,X'S) H ( 111,X'S) H ( 112,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 25,X'S) H ( 251,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 09/05/13 at 21:14:30 # #LIST 16 SAME C(21) CL(22) CL(23) CL(24) AND CONT C(21) CL(23) CL(24) CL(22) AND CONT C(21) CL(24) CL(22) CL(23) AND CONT C(25) CL(26) CL(27) CL(28) AND CONT C(25) CL(27) CL(28) CL(26) AND CONT C(25) CL(28) CL(26) CL(27) SIMU 0.01 C(21) CL(22) CL(23) CL(24) AND CONT C(21) CL(23) CL(24) CL(22) AND CONT C(21) CL(24) CL(22) CL(23) AND CONT C(25) CL(26) CL(27) CL(28) AND CONT C(25) CL(27) CL(28) CL(26) AND CONT C(25) CL(28) CL(26) CL(27) DELU 0.01 C(21) CL(22) CL(23) CL(24) AND CONT C(21) CL(23) CL(24) CL(22) AND CONT C(21) CL(24) CL(22) CL(23) AND CONT C(25) CL(26) CL(27) CL(28) AND CONT C(25) CL(27) CL(28) CL(26) AND CONT C(25) CL(28) CL(26) CL(27) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #============================================================================== data_15a #============================================================================== _audit_creation_date "12-12-18" _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title '021djd12' _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 10.4507(1) _cell_length_b 16.2752(2) _cell_length_c 11.5043(1) _cell_angle_alpha 90 _cell_angle_beta 101.0903(5) _cell_angle_gamma 90 _cell_volume 1920.19(3) _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,y+1/2,-z' 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' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 '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' 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 = C21 H21 Br1 N2 O2 S1 # Dc = 1.54 Fooo = 912.00 Mu = 22.69 M = 890.76 # Found Formula = C21 H21 Br1 N2 O2 S1 # Dc = 1.54 FOOO = 912.00 Mu = 22.69 M = 890.76 _chemical_formula_sum 'C21 H21 Br1 N2 O2 S1' _chemical_formula_moiety 'C21 H21 Br1 N2 O2 S1' _chemical_compound_source . _chemical_formula_weight 445.38 _cell_measurement_reflns_used 4512 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.269 # Sheldrick geometric approximatio 0.51 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.71 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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 150 _diffrn_reflns_number 35947 _reflns_number_total 8412 _diffrn_reflns_av_R_equivalents 0.063 # Number of reflections without Friedels Law is 8412 # Number of reflections with Friedels Law is 4514 # Theoretical number of reflections is about 4403 _diffrn_reflns_theta_min 5.103 _diffrn_reflns_theta_max 27.481 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.481 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -21 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 2.35 _oxford_diffrn_Wilson_scale 5.35 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.93 _refine_diff_density_max 1.11 # 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>-3.0\s(I) _refine_ls_number_reflns 8412 _refine_ls_number_restraints 1 _refine_ls_number_parameters 488 _oxford_refine_ls_R_factor_ref 0.0325 _refine_ls_wR_factor_ref 0.0635 _refine_ls_goodness_of_fit_ref 0.9896 _refine_ls_shift/su_max 0.0005728 _refine_ls_shift/su_mean 0.0000319 # The values computed with all filters except I/sigma _oxford_reflns_number_all 8412 _refine_ls_R_factor_all 0.0325 _refine_ls_wR_factor_all 0.0635 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7894 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_gt 0.0616 _refine_ls_abs_structure_Flack 0.010(4) _refine_ls_abs_structure_details 'Flack (1983), 3898 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.16P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. 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. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 Br1 Br 1.41297(2) 0.38134(3) 0.34172(2) 0.0285 1.0000 Uani . . . . . . C2 C 1.3005(2) 0.46900(15) 0.2792(2) 0.0226 1.0000 Uani . . . . . . C3 C 1.1759(2) 0.45052(14) 0.2192(2) 0.0208 1.0000 Uani . . . . . . C4 C 1.0911(2) 0.51396(14) 0.1758(2) 0.0205 1.0000 Uani . . . . . . C5 C 1.1330(2) 0.59512(15) 0.1918(2) 0.0256 1.0000 Uani . . . . . . C6 C 1.2588(3) 0.61223(16) 0.2519(2) 0.0295 1.0000 Uani . . . . . . C7 C 1.3438(2) 0.54976(17) 0.2968(2) 0.0287 1.0000 Uani . . . . . . C8 C 0.9538(2) 0.49079(14) 0.1142(2) 0.0228 1.0000 Uani . . . . . . N9 N 0.86899(18) 0.56083(12) 0.08136(17) 0.0205 1.0000 Uani . . . . . . C10 C 0.8749(2) 0.60797(14) -0.0176(2) 0.0206 1.0000 Uani . . . . . . C11 C 0.9386(2) 0.59243(16) -0.1112(2) 0.0245 1.0000 Uani . . . . . . C12 C 0.9203(3) 0.64855(17) -0.2034(2) 0.0276 1.0000 Uani . . . . . . C13 C 0.8431(2) 0.71881(16) -0.2021(2) 0.0263 1.0000 Uani . . . . . . C14 C 0.7847(2) 0.73585(15) -0.1068(2) 0.0247 1.0000 Uani . . . . . . C15 C 0.8018(2) 0.68067(14) -0.0121(2) 0.0211 1.0000 Uani . . . . . . C16 C 0.7523(2) 0.67577(14) 0.0958(2) 0.0209 1.0000 Uani . . . . . . C17 C 0.7947(2) 0.60349(14) 0.1504(2) 0.0201 1.0000 Uani . . . . . . C18 C 0.7553(2) 0.56948(14) 0.2609(2) 0.0213 1.0000 Uani . . . . . . N19 N 0.66573(19) 0.63045(12) 0.30024(17) 0.0222 1.0000 Uani . . . . . . S20 S 0.72133(6) 0.66744(5) 0.43267(5) 0.0261 1.0000 Uani . . . . . . O21 O 0.6787(2) 0.61696(14) 0.51981(17) 0.0420 1.0000 Uani . . . . . . O22 O 0.6911(2) 0.75361(12) 0.43494(18) 0.0378 1.0000 Uani . . . . . . C23 C 0.8865(3) 0.64467(16) 0.4315(2) 0.0296 1.0000 Uani . . . . . . C24 C 0.8725(3) 0.56237(15) 0.3669(2) 0.0263 1.0000 Uani . . . . . . C25 C 0.5806(2) 0.68198(16) 0.2122(2) 0.0268 1.0000 Uani . . . . . . C26 C 0.6594(2) 0.73246(16) 0.1396(2) 0.0266 1.0000 Uani . . . . . . C27 C 0.6827(3) 0.48793(16) 0.2380(3) 0.0307 1.0000 Uani . . . . . . Br28 Br 0.97901(3) 0.32754(3) 0.39862(3) 0.0391 1.0000 Uani . . . . . . C29 C 0.8383(2) 0.32493(17) 0.4816(2) 0.0267 1.0000 Uani . . . . . . C30 C 0.7437(3) 0.26470(16) 0.4539(2) 0.0289 1.0000 Uani . . . . . . C31 C 0.6397(3) 0.26565(16) 0.5129(2) 0.0274 1.0000 Uani . . . . . . C32 C 0.6313(2) 0.32589(16) 0.5970(2) 0.0230 1.0000 Uani . . . . . . C33 C 0.7276(2) 0.38529(16) 0.62490(18) 0.0207 1.0000 Uani . . . . . . C34 C 0.8335(2) 0.38422(16) 0.56645(19) 0.0224 1.0000 Uani . . . . . . C35 C 0.7227(2) 0.45407(15) 0.7126(2) 0.0227 1.0000 Uani . . . . . . N36 N 0.64904(19) 0.43309(12) 0.80417(17) 0.0219 1.0000 Uani . . . . . . C37 C 0.6932(2) 0.37513(16) 0.89065(19) 0.0228 1.0000 Uani . . . . . . C38 C 0.6024(2) 0.36932(15) 0.9660(2) 0.0233 1.0000 Uani . . . . . . C39 C 0.4999(2) 0.42615(15) 0.9219(2) 0.0229 1.0000 Uani . . . . . . C40 C 0.5304(2) 0.46350(14) 0.8242(2) 0.0210 1.0000 Uani . . . . . . C41 C 0.4522(2) 0.53135(14) 0.7525(2) 0.0216 1.0000 Uani . . . . . . N42 N 0.32641(19) 0.53898(13) 0.79549(18) 0.0241 1.0000 Uani . . . . . . S43 S 0.20060(6) 0.50210(5) 0.70227(6) 0.0298 1.0000 Uani . . . . . . O44 O 0.1293(2) 0.56807(15) 0.63536(19) 0.0477 1.0000 Uani . . . . . . O45 O 0.1262(2) 0.44851(15) 0.76296(19) 0.0450 1.0000 Uani . . . . . . C46 C 0.2931(2) 0.45221(17) 0.6100(2) 0.0296 1.0000 Uani . . . . . . C47 C 0.4093(2) 0.50934(15) 0.6192(2) 0.0253 1.0000 Uani . . . . . . C48 C 0.3300(3) 0.53143(17) 0.9239(2) 0.0290 1.0000 Uani . . . . . . C49 C 0.3814(2) 0.44762(16) 0.9713(2) 0.0271 1.0000 Uani . . . . . . C50 C 0.5235(3) 0.61384(15) 0.7699(2) 0.0287 1.0000 Uani . . . . . . C51 C 0.6273(3) 0.31427(16) 1.0623(2) 0.0300 1.0000 Uani . . . . . . C52 C 0.7391(3) 0.26805(17) 1.0798(2) 0.0363 1.0000 Uani . . . . . . C53 C 0.8298(3) 0.27482(17) 1.0041(2) 0.0339 1.0000 Uani . . . . . . C54 C 0.8077(2) 0.32787(17) 0.9083(2) 0.0299 1.0000 Uani . . . . . . H31 H 1.1491 0.3960 0.2068 0.0270 1.0000 Uiso R . . . . . H51 H 1.0756 0.6379 0.1623 0.0299 1.0000 Uiso R . . . . . H61 H 1.2857 0.6670 0.2623 0.0363 1.0000 Uiso R . . . . . H71 H 1.4282 0.5614 0.3364 0.0342 1.0000 Uiso R . . . . . H81 H 0.9166 0.4571 0.1684 0.0282 1.0000 Uiso R . . . . . H82 H 0.9589 0.4601 0.0431 0.0281 1.0000 Uiso R . . . . . H111 H 0.9921 0.5464 -0.1109 0.0302 1.0000 Uiso R . . . . . H121 H 0.9601 0.6385 -0.2681 0.0355 1.0000 Uiso R . . . . . H131 H 0.8301 0.7549 -0.2672 0.0273 1.0000 Uiso R . . . . . H141 H 0.7350 0.7834 -0.1051 0.0321 1.0000 Uiso R . . . . . H231 H 0.9229 0.6857 0.3847 0.0360 1.0000 Uiso R . . . . . H232 H 0.9390 0.6411 0.5113 0.0359 1.0000 Uiso R . . . . . H241 H 0.8532 0.5197 0.4199 0.0333 1.0000 Uiso R . . . . . H242 H 0.9514 0.5494 0.3388 0.0331 1.0000 Uiso R . . . . . H251 H 0.5302 0.7191 0.2529 0.0329 1.0000 Uiso R . . . . . H252 H 0.5226 0.6463 0.1588 0.0332 1.0000 Uiso R . . . . . H262 H 0.7075 0.7748 0.1883 0.0328 1.0000 Uiso R . . . . . H261 H 0.6021 0.7573 0.0731 0.0329 1.0000 Uiso R . . . . . H272 H 0.6491 0.4727 0.3074 0.0469 1.0000 Uiso R . . . . . H271 H 0.6120 0.4938 0.1716 0.0470 1.0000 Uiso R . . . . . H273 H 0.7424 0.4459 0.2212 0.0471 1.0000 Uiso R . . . . . H301 H 0.7504 0.2247 0.3964 0.0338 1.0000 Uiso R . . . . . H311 H 0.5751 0.2252 0.4965 0.0308 1.0000 Uiso R . . . . . H321 H 0.5599 0.3262 0.6348 0.0293 1.0000 Uiso R . . . . . H341 H 0.9011 0.4224 0.5859 0.0268 1.0000 Uiso R . . . . . H351 H 0.6820 0.5011 0.6698 0.0308 1.0000 Uiso R . . . . . H352 H 0.8113 0.4677 0.7496 0.0309 1.0000 Uiso R . . . . . H462 H 0.2456 0.4477 0.5289 0.0352 1.0000 Uiso R . . . . . H461 H 0.3205 0.3981 0.6406 0.0348 1.0000 Uiso R . . . . . H472 H 0.3853 0.5577 0.5718 0.0322 1.0000 Uiso R . . . . . H471 H 0.4803 0.4814 0.5922 0.0319 1.0000 Uiso R . . . . . H481 H 0.2415 0.5390 0.9379 0.0329 1.0000 Uiso R . . . . . H482 H 0.3877 0.5736 0.9652 0.0330 1.0000 Uiso R . . . . . H491 H 0.4041 0.4489 1.0576 0.0331 1.0000 Uiso R . . . . . H492 H 0.3152 0.4064 0.9474 0.0330 1.0000 Uiso R . . . . . H501 H 0.4693 0.6565 0.7280 0.0460 1.0000 Uiso R . . . . . H502 H 0.5448 0.6273 0.8528 0.0461 1.0000 Uiso R . . . . . H503 H 0.6027 0.6101 0.7397 0.0461 1.0000 Uiso R . . . . . H511 H 0.5675 0.3105 1.1133 0.0423 1.0000 Uiso R . . . . . H521 H 0.7544 0.2303 1.1425 0.0472 1.0000 Uiso R . . . . . H531 H 0.9059 0.2427 1.0187 0.0368 1.0000 Uiso R . . . . . H541 H 0.8669 0.3322 0.8573 0.0380 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 Br1 0.02460(11) 0.03028(12) 0.02933(12) 0.00640(11) 0.00169(9) 0.00474(10) C2 0.0225(11) 0.0244(11) 0.0212(11) 0.0025(9) 0.0049(9) 0.0034(9) C3 0.0221(11) 0.0198(11) 0.0216(11) 0.0010(9) 0.0071(9) 0.0010(9) C4 0.0211(11) 0.0217(12) 0.0193(11) -0.0025(9) 0.0053(9) 0.0015(9) C5 0.0250(12) 0.0211(12) 0.0296(13) 0.0006(10) 0.0022(10) 0.0010(10) C6 0.0307(13) 0.0213(12) 0.0357(14) -0.0021(10) 0.0047(11) -0.0051(10) C7 0.0239(12) 0.0358(14) 0.0255(12) -0.0023(11) 0.0029(10) -0.0033(11) C8 0.0211(11) 0.0190(11) 0.0275(12) -0.0028(9) 0.0028(9) 0.0031(9) N9 0.0204(9) 0.0188(9) 0.0222(10) -0.0018(8) 0.0039(8) 0.0031(8) C10 0.0181(10) 0.0222(11) 0.0208(11) -0.0024(9) 0.0019(8) -0.0010(9) C11 0.0217(11) 0.0272(12) 0.0252(12) -0.0054(10) 0.0062(9) -0.0006(10) C12 0.0286(13) 0.0353(14) 0.0207(12) -0.0070(10) 0.0097(10) -0.0091(10) C13 0.0293(13) 0.0282(13) 0.0221(12) 0.0017(10) 0.0063(10) -0.0063(11) C14 0.0261(12) 0.0227(11) 0.0256(12) 0.0021(10) 0.0059(10) -0.0009(10) C15 0.0206(11) 0.0223(11) 0.0204(11) -0.0022(9) 0.0040(9) 0.0013(9) C16 0.0207(11) 0.0223(11) 0.0204(11) -0.0001(9) 0.0056(9) 0.0025(9) C17 0.0197(11) 0.0213(11) 0.0191(11) -0.0020(9) 0.0033(9) -0.0005(9) C18 0.0211(11) 0.0206(11) 0.0224(11) 0.0006(9) 0.0051(9) 0.0025(9) N19 0.0223(10) 0.0258(10) 0.0189(9) -0.0012(8) 0.0052(8) 0.0033(8) S20 0.0333(3) 0.0253(3) 0.0204(3) -0.0016(2) 0.0068(2) 0.0026(3) O21 0.0581(13) 0.0468(12) 0.0250(10) 0.0065(9) 0.0174(9) 0.0043(10) O22 0.0465(12) 0.0251(10) 0.0408(11) -0.0097(8) 0.0060(9) 0.0051(9) C23 0.0278(13) 0.0338(14) 0.0250(13) -0.0035(10) -0.0009(10) 0.0028(11) C24 0.0294(13) 0.0262(12) 0.0224(12) 0.0026(10) 0.0031(10) 0.0048(10) C25 0.0240(12) 0.0345(14) 0.0225(12) 0.0019(10) 0.0055(9) 0.0092(10) C26 0.0300(13) 0.0259(12) 0.0251(12) 0.0045(10) 0.0083(10) 0.0092(10) C27 0.0299(13) 0.0255(13) 0.0386(15) -0.0017(11) 0.0113(11) -0.0049(10) Br28 0.04223(16) 0.04041(15) 0.04193(16) 0.00676(13) 0.02604(12) 0.01248(13) C29 0.0299(12) 0.0266(11) 0.0256(12) 0.0067(10) 0.0104(9) 0.0087(11) C30 0.0406(15) 0.0255(12) 0.0206(12) -0.0031(10) 0.0056(10) 0.0056(11) C31 0.0311(13) 0.0233(12) 0.0257(12) -0.0011(10) 0.0004(10) -0.0036(10) C32 0.0221(11) 0.0242(11) 0.0229(11) 0.0030(10) 0.0045(9) 0.0000(10) C33 0.0203(10) 0.0216(10) 0.0198(10) 0.0033(10) 0.0032(8) 0.0025(10) C34 0.0206(10) 0.0237(11) 0.0235(10) 0.0046(10) 0.0061(8) 0.0018(10) C35 0.0211(11) 0.0245(12) 0.0238(12) -0.0021(9) 0.0076(9) -0.0027(9) N36 0.0241(10) 0.0210(10) 0.0210(10) 0.0009(8) 0.0056(8) 0.0024(8) C37 0.0288(11) 0.0205(11) 0.0176(10) -0.0038(9) 0.0012(8) -0.0001(11) C38 0.0268(11) 0.0230(12) 0.0185(10) -0.0027(9) -0.0001(9) -0.0006(10) C39 0.0251(12) 0.0239(12) 0.0193(11) -0.0024(9) 0.0036(9) -0.0024(9) C40 0.0204(11) 0.0214(11) 0.0213(11) -0.0035(9) 0.0044(9) -0.0007(9) C41 0.0252(12) 0.0207(11) 0.0193(11) -0.0021(9) 0.0056(9) 0.0018(9) N42 0.0234(10) 0.0258(10) 0.0230(10) -0.0047(8) 0.0044(8) 0.0036(8) S43 0.0215(3) 0.0392(4) 0.0274(3) -0.0061(3) 0.0012(2) 0.0046(3) O44 0.0384(11) 0.0639(15) 0.0374(11) -0.0022(10) -0.0014(9) 0.0288(11) O45 0.0324(10) 0.0618(14) 0.0418(11) -0.0119(10) 0.0094(9) -0.0150(10) C46 0.0263(13) 0.0342(14) 0.0270(13) -0.0089(11) 0.0021(10) 0.0038(11) C47 0.0301(13) 0.0265(12) 0.0185(11) -0.0013(9) 0.0032(9) 0.0045(10) C48 0.0285(13) 0.0356(14) 0.0242(12) -0.0088(10) 0.0082(10) 0.0016(11) C49 0.0254(12) 0.0358(14) 0.0208(12) -0.0017(10) 0.0063(9) -0.0038(11) C50 0.0325(13) 0.0211(12) 0.0326(13) -0.0024(10) 0.0068(11) 0.0005(10) C51 0.0403(14) 0.0284(13) 0.0198(11) -0.0004(10) 0.0022(10) -0.0037(11) C52 0.0541(18) 0.0255(13) 0.0247(13) 0.0015(10) -0.0037(12) 0.0014(12) C53 0.0378(15) 0.0278(13) 0.0309(14) -0.0032(11) -0.0060(11) 0.0115(11) C54 0.0316(13) 0.0286(12) 0.0275(12) -0.0062(11) 0.0007(10) 0.0061(11) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 0.4366(3) 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 Br1 . C2 . 1.900(2) yes C2 . C3 . 1.385(3) yes C2 . C7 . 1.392(4) yes C3 . C4 . 1.389(3) yes C3 . H31 . 0.933 no C4 . C5 . 1.393(3) yes C4 . C8 . 1.521(3) yes C5 . C6 . 1.390(4) yes C5 . H51 . 0.938 no C6 . C7 . 1.383(4) yes C6 . H61 . 0.936 no C7 . H71 . 0.931 no C8 . N9 . 1.449(3) yes C8 . H81 . 0.967 no C8 . H82 . 0.969 no N9 . C10 . 1.384(3) yes N9 . C17 . 1.397(3) yes C10 . C11 . 1.394(3) yes C10 . C15 . 1.416(3) yes C11 . C12 . 1.384(4) yes C11 . H111 . 0.934 no C12 . C13 . 1.401(4) yes C12 . H121 . 0.935 no C13 . C14 . 1.382(4) yes C13 . H131 . 0.941 no C14 . C15 . 1.396(3) yes C14 . H141 . 0.934 no C15 . C16 . 1.437(3) yes C16 . C17 . 1.367(3) yes C16 . C26 . 1.495(3) yes C17 . C18 . 1.515(3) yes C18 . N19 . 1.493(3) yes C18 . C24 . 1.557(3) yes C18 . C27 . 1.526(3) yes N19 . S20 . 1.637(2) yes N19 . C25 . 1.475(3) yes S20 . O21 . 1.432(2) yes S20 . O22 . 1.4389(19) yes S20 . C23 . 1.768(3) yes C23 . C24 . 1.525(4) yes C23 . H231 . 0.980 no C23 . H232 . 0.976 no C24 . H241 . 0.971 no C24 . H242 . 0.966 no C25 . C26 . 1.522(3) yes C25 . H251 . 0.978 no C25 . H252 . 0.969 no C26 . H262 . 0.966 no C26 . H261 . 0.964 no C27 . H272 . 0.964 no C27 . H271 . 0.960 no C27 . H273 . 0.970 no Br28 . C29 . 1.901(2) yes C29 . C30 . 1.386(4) yes C29 . C34 . 1.381(4) yes C30 . C31 . 1.387(4) yes C30 . H301 . 0.940 no C31 . C32 . 1.392(4) yes C31 . H311 . 0.936 no C32 . C33 . 1.388(3) yes C32 . H321 . 0.934 no C33 . C34 . 1.401(3) yes C33 . C35 . 1.514(3) yes C34 . H341 . 0.935 no C35 . N36 . 1.460(3) yes C35 . H351 . 0.963 no C35 . H352 . 0.968 no N36 . C37 . 1.384(3) yes N36 . C40 . 1.395(3) yes C37 . C38 . 1.406(3) yes C37 . C54 . 1.404(3) yes C38 . C39 . 1.432(3) yes C38 . C51 . 1.410(3) yes C39 . C40 . 1.368(3) yes C39 . C49 . 1.500(3) yes C40 . C41 . 1.519(3) yes C41 . N42 . 1.497(3) yes C41 . C47 . 1.554(3) yes C41 . C50 . 1.529(3) yes N42 . S43 . 1.642(2) yes N42 . C48 . 1.475(3) yes S43 . O44 . 1.442(2) yes S43 . O45 . 1.436(2) yes S43 . C46 . 1.765(3) yes C46 . C47 . 1.517(4) yes C46 . H462 . 0.972 no C46 . H461 . 0.971 no C47 . H472 . 0.963 no C47 . H471 . 0.971 no C48 . C49 . 1.528(4) yes C48 . H481 . 0.977 no C48 . H482 . 0.975 no C49 . H491 . 0.976 no C49 . H492 . 0.965 no C50 . H501 . 0.964 no C50 . H502 . 0.962 no C50 . H503 . 0.960 no C51 . C52 . 1.372(4) yes C51 . H511 . 0.938 no C52 . C53 . 1.409(4) yes C52 . H521 . 0.938 no C53 . C54 . 1.384(4) yes C53 . H531 . 0.940 no C54 . H541 . 0.933 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 Br1 . C2 . C3 . 118.66(18) yes Br1 . C2 . C7 . 119.59(18) yes C3 . C2 . C7 . 121.7(2) yes C2 . C3 . C4 . 119.4(2) yes C2 . C3 . H31 . 120.6 no C4 . C3 . H31 . 120.0 no C3 . C4 . C5 . 119.7(2) yes C3 . C4 . C8 . 117.6(2) yes C5 . C4 . C8 . 122.8(2) yes C4 . C5 . C6 . 119.9(2) yes C4 . C5 . H51 . 119.5 no C6 . C5 . H51 . 120.6 no C5 . C6 . C7 . 121.1(2) yes C5 . C6 . H61 . 119.1 no C7 . C6 . H61 . 119.8 no C2 . C7 . C6 . 118.2(2) yes C2 . C7 . H71 . 121.0 no C6 . C7 . H71 . 120.8 no C4 . C8 . N9 . 113.68(19) yes C4 . C8 . H81 . 107.5 no N9 . C8 . H81 . 108.3 no C4 . C8 . H82 . 108.7 no N9 . C8 . H82 . 108.4 no H81 . C8 . H82 . 110.3 no C8 . N9 . C10 . 121.95(19) yes C8 . N9 . C17 . 128.4(2) yes C10 . N9 . C17 . 108.04(18) yes N9 . C10 . C11 . 129.7(2) yes N9 . C10 . C15 . 108.5(2) yes C11 . C10 . C15 . 121.9(2) yes C10 . C11 . C12 . 117.1(2) yes C10 . C11 . H111 . 121.1 no C12 . C11 . H111 . 121.8 no C11 . C12 . C13 . 121.7(2) yes C11 . C12 . H121 . 118.5 no C13 . C12 . H121 . 119.8 no C12 . C13 . C14 . 121.0(2) yes C12 . C13 . H131 . 119.8 no C14 . C13 . H131 . 119.2 no C13 . C14 . C15 . 118.7(2) yes C13 . C14 . H141 . 121.0 no C15 . C14 . H141 . 120.4 no C10 . C15 . C14 . 119.5(2) yes C10 . C15 . C16 . 106.2(2) yes C14 . C15 . C16 . 134.1(2) yes C15 . C16 . C17 . 107.8(2) yes C15 . C16 . C26 . 128.5(2) yes C17 . C16 . C26 . 123.4(2) yes N9 . C17 . C16 . 109.5(2) yes N9 . C17 . C18 . 124.5(2) yes C16 . C17 . C18 . 125.7(2) yes C17 . C18 . N19 . 107.40(18) yes C17 . C18 . C24 . 112.60(19) yes N19 . C18 . C24 . 104.89(19) yes C17 . C18 . C27 . 112.3(2) yes N19 . C18 . C27 . 108.10(19) yes C24 . C18 . C27 . 111.1(2) yes C18 . N19 . S20 . 113.29(15) yes C18 . N19 . C25 . 120.05(18) yes S20 . N19 . C25 . 119.29(16) yes N19 . S20 . O21 . 109.75(12) yes N19 . S20 . O22 . 109.60(11) yes O21 . S20 . O22 . 116.58(13) yes N19 . S20 . C23 . 95.05(11) yes O21 . S20 . C23 . 108.72(13) yes O22 . S20 . C23 . 115.00(13) yes S20 . C23 . C24 . 100.68(17) yes S20 . C23 . H231 . 110.1 no C24 . C23 . H231 . 110.0 no S20 . C23 . H232 . 112.2 no C24 . C23 . H232 . 113.0 no H231 . C23 . H232 . 110.5 no C23 . C24 . C18 . 107.68(19) yes C23 . C24 . H241 . 109.5 no C18 . C24 . H241 . 108.6 no C23 . C24 . H242 . 110.3 no C18 . C24 . H242 . 110.4 no H241 . C24 . H242 . 110.3 no N19 . C25 . C26 . 111.43(19) yes N19 . C25 . H251 . 109.4 no C26 . C25 . H251 . 109.1 no N19 . C25 . H252 . 108.4 no C26 . C25 . H252 . 108.3 no H251 . C25 . H252 . 110.2 no C25 . C26 . C16 . 107.9(2) yes C25 . C26 . H262 . 110.1 no C16 . C26 . H262 . 109.7 no C25 . C26 . H261 . 110.0 no C16 . C26 . H261 . 109.6 no H262 . C26 . H261 . 109.6 no C18 . C27 . H272 . 109.2 no C18 . C27 . H271 . 109.4 no H272 . C27 . H271 . 109.7 no C18 . C27 . H273 . 109.3 no H272 . C27 . H273 . 109.5 no H271 . C27 . H273 . 109.8 no Br28 . C29 . C30 . 119.17(19) yes Br28 . C29 . C34 . 118.45(19) yes C30 . C29 . C34 . 122.4(2) yes C29 . C30 . C31 . 118.1(2) yes C29 . C30 . H301 . 120.3 no C31 . C30 . H301 . 121.6 no C30 . C31 . C32 . 120.5(2) yes C30 . C31 . H311 . 119.7 no C32 . C31 . H311 . 119.8 no C31 . C32 . C33 . 120.8(2) yes C31 . C32 . H321 . 119.4 no C33 . C32 . H321 . 119.8 no C32 . C33 . C34 . 119.0(2) yes C32 . C33 . C35 . 123.6(2) yes C34 . C33 . C35 . 117.4(2) yes C33 . C34 . C29 . 119.2(2) yes C33 . C34 . H341 . 120.5 no C29 . C34 . H341 . 120.3 no C33 . C35 . N36 . 113.44(19) yes C33 . C35 . H351 . 108.4 no N36 . C35 . H351 . 108.2 no C33 . C35 . H352 . 108.1 no N36 . C35 . H352 . 109.2 no H351 . C35 . H352 . 109.5 no C35 . N36 . C37 . 121.92(19) yes C35 . N36 . C40 . 130.2(2) yes C37 . N36 . C40 . 107.90(19) yes N36 . C37 . C38 . 108.5(2) yes N36 . C37 . C54 . 129.4(2) yes C38 . C37 . C54 . 122.1(2) yes C37 . C38 . C39 . 106.6(2) yes C37 . C38 . C51 . 118.8(2) yes C39 . C38 . C51 . 134.6(2) yes C38 . C39 . C40 . 107.6(2) yes C38 . C39 . C49 . 129.2(2) yes C40 . C39 . C49 . 123.2(2) yes N36 . C40 . C39 . 109.4(2) yes N36 . C40 . C41 . 124.8(2) yes C39 . C40 . C41 . 125.7(2) yes C40 . C41 . N42 . 107.20(18) yes C40 . C41 . C47 . 113.02(19) yes N42 . C41 . C47 . 103.86(18) yes C40 . C41 . C50 . 111.70(19) yes N42 . C41 . C50 . 108.67(19) yes C47 . C41 . C50 . 111.9(2) yes C41 . N42 . S43 . 113.44(15) yes C41 . N42 . C48 . 117.98(19) yes S43 . N42 . C48 . 119.11(17) yes N42 . S43 . O44 . 110.06(13) yes N42 . S43 . O45 . 110.16(12) yes O44 . S43 . O45 . 116.07(14) yes N42 . S43 . C46 . 95.66(11) yes O44 . S43 . C46 . 107.95(13) yes O45 . S43 . C46 . 115.04(14) yes S43 . C46 . C47 . 101.51(17) yes S43 . C46 . H462 . 112.0 no C47 . C46 . H462 . 111.6 no S43 . C46 . H461 . 110.9 no C47 . C46 . H461 . 110.7 no H462 . C46 . H461 . 109.9 no C41 . C47 . C46 . 106.6(2) yes C41 . C47 . H472 . 111.4 no C46 . C47 . H472 . 110.1 no C41 . C47 . H471 . 109.3 no C46 . C47 . H471 . 109.9 no H472 . C47 . H471 . 109.4 no N42 . C48 . C49 . 111.8(2) yes N42 . C48 . H481 . 108.2 no C49 . C48 . H481 . 109.4 no N42 . C48 . H482 . 108.9 no C49 . C48 . H482 . 108.2 no H481 . C48 . H482 . 110.3 no C48 . C49 . C39 . 109.4(2) yes C48 . C49 . H491 . 110.1 no C39 . C49 . H491 . 109.5 no C48 . C49 . H492 . 109.6 no C39 . C49 . H492 . 109.2 no H491 . C49 . H492 . 109.0 no C41 . C50 . H501 . 110.0 no C41 . C50 . H502 . 110.1 no H501 . C50 . H502 . 109.5 no C41 . C50 . H503 . 109.2 no H501 . C50 . H503 . 109.2 no H502 . C50 . H503 . 108.8 no C38 . C51 . C52 . 119.1(2) yes C38 . C51 . H511 . 119.2 no C52 . C51 . H511 . 121.7 no C51 . C52 . C53 . 121.5(2) yes C51 . C52 . H521 . 119.1 no C53 . C52 . H521 . 119.4 no C52 . C53 . C54 . 120.8(2) yes C52 . C53 . H531 . 119.5 no C54 . C53 . H531 . 119.7 no C37 . C54 . C53 . 117.6(2) yes C37 . C54 . H541 . 121.1 no C53 . C54 . H541 . 121.2 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 C12 . H121 . O44 1_654 152.04 0.935 2.535 3.390(4) yes C23 . H232 . O44 1_655 143.37 0.976 2.513 3.347(4) yes C35 . H351 . O21 . 151.60 0.963 2.552 3.430(4) yes C46 . H461 . O22 2_646 137.31 0.971 2.502 3.282(4) yes _iucr_refine_instruction_details_constraints ; # # Punched on 18/12/12 at 10:54:54 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 23,X'S) H ( 231,X'S) H ( 232,X'S) RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) RIDE C ( 25,X'S) H ( 251,X'S) H ( 252,X'S) RIDE C ( 26,X'S) H ( 262,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 272,X'S) H ( 271,X'S) H ( 273,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) H ( 352,X'S) RIDE C ( 46,X'S) H ( 462,X'S) H ( 461,X'S) RIDE C ( 47,X'S) H ( 472,X'S) H ( 471,X'S) RIDE C ( 48,X'S) H ( 481,X'S) H ( 482,X'S) RIDE C ( 49,X'S) H ( 491,X'S) H ( 492,X'S) RIDE C ( 50,X'S) H ( 501,X'S) H ( 502,X'S) H ( 503,X'S) RIDE C ( 51,X'S) H ( 511,X'S) RIDE C ( 52,X'S) H ( 521,X'S) RIDE C ( 53,X'S) H ( 531,X'S) RIDE C ( 54,X'S) H ( 541,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 18/12/12 at 10:54:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;