# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Catherine E. Housecroft' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Edwin Constable' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Markus Neuburger' '' '' 'Jason Price' '' '' 'Jennifer A. Zampese' '' '' _publ_contact_author_name 'Catherine E Housecroft' _publ_contact_author_address ; Departement Chemie University of Basel Spitalstrasse 51 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ;Switchable ligands in copper(I) coordination chemistry: thione and oligosulfide-bridged 6-methyl-2,2'-bipyridines ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # 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. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment 'JP143.CIF' data_jp143 _database_code_depnum_ccdc_archive 'CCDC 765876' #TrackingRef 'JP143.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C66 H58 Cu2 N12 S6, 2(F6 P)' _chemical_formula_sum 'C66 H58 Cu2 F12 N12 P2 S6' _chemical_formula_weight 1628.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.652(6) _cell_length_b 13.133(3) _cell_length_c 17.790(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.62(3) _cell_angle_gamma 90.00 _cell_volume 6826(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3320 _exptl_absorpt_coefficient_mu 0.939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6410 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50652 _diffrn_reflns_av_R_equivalents 0.0894 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7833 _reflns_number_gt 7102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+12.9555P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7833 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.133071(9) 0.62268(2) 0.423126(17) 0.02733(9) Uani 1 1 d . . . S1 S 0.03449(2) 0.65583(5) 0.28031(4) 0.03699(15) Uani 1 1 d . . . N1 N 0.17471(6) 0.72230(15) 0.51496(11) 0.0267(4) Uani 1 1 d . . . N2 N 0.08932(6) 0.74829(15) 0.40930(12) 0.0270(4) Uani 1 1 d . . . C1 C 0.23974(9) 0.6069(2) 0.55116(17) 0.0425(6) Uani 1 1 d . . . H1A H 0.2252 0.5479 0.5650 0.064 Uiso 1 1 calc R . . H1B H 0.2725 0.6071 0.5854 0.064 Uiso 1 1 calc R . . H1C H 0.2356 0.6030 0.4937 0.064 Uiso 1 1 calc R . . C2 C 0.21813(8) 0.7032(2) 0.56551(14) 0.0317(5) Uani 1 1 d . . . C3 C 0.24178(9) 0.7697(2) 0.62858(15) 0.0396(6) Uani 1 1 d . . . H3A H 0.2726 0.7560 0.6636 0.047 Uiso 1 1 calc R . . C4 C 0.21988(10) 0.8558(2) 0.63960(16) 0.0424(6) Uani 1 1 d . . . H4A H 0.2356 0.9023 0.6821 0.051 Uiso 1 1 calc R . . C5 C 0.17492(10) 0.8743(2) 0.58849(16) 0.0371(6) Uani 1 1 d . . . H5A H 0.1591 0.9323 0.5962 0.045 Uiso 1 1 calc R . . C6 C 0.15341(8) 0.80626(18) 0.52582(14) 0.0279(4) Uani 1 1 d . . . C7 C 0.10528(8) 0.82025(18) 0.46721(14) 0.0293(5) Uani 1 1 d . . . C8 C 0.07735(11) 0.9000(2) 0.47151(17) 0.0422(6) Uani 1 1 d . . . H8A H 0.0889 0.9515 0.5118 0.051 Uiso 1 1 calc R . . C9 C 0.03241(11) 0.9030(3) 0.4159(2) 0.0492(7) Uani 1 1 d . . . H9A H 0.0127 0.9561 0.4188 0.059 Uiso 1 1 calc R . . C10 C 0.01611(10) 0.8297(2) 0.35639(18) 0.0429(6) Uani 1 1 d . . . H10A H -0.0146 0.8310 0.3179 0.052 Uiso 1 1 calc R . . C11 C 0.04627(8) 0.75387(19) 0.35488(15) 0.0317(5) Uani 1 1 d . . . S2 S 0.14943(2) 0.60323(4) 0.31321(4) 0.02963(13) Uani 1 1 d . . . N3 N 0.19367(7) 0.30321(16) 0.49372(12) 0.0295(4) Uani 1 1 d . . . N4 N 0.17124(6) 0.41079(15) 0.36091(11) 0.0239(4) Uani 1 1 d . . . H4B H 0.1748 0.4329 0.4097 0.029 Uiso 1 1 calc R . . C12 C 0.20962(11) 0.3192(3) 0.63747(16) 0.0461(7) Uani 1 1 d . . . H12A H 0.2418 0.3398 0.6626 0.069 Uiso 1 1 calc R . . H12B H 0.2014 0.2803 0.6769 0.069 Uiso 1 1 calc R . . H12C H 0.1902 0.3799 0.6207 0.069 Uiso 1 1 calc R . . C13 C 0.20267(9) 0.2541(2) 0.56419(16) 0.0358(5) Uani 1 1 d . . . C14 C 0.20504(10) 0.1484(2) 0.56843(19) 0.0447(7) Uani 1 1 d . . . H14A H 0.2118 0.1147 0.6190 0.054 Uiso 1 1 calc R . . C15 C 0.19748(11) 0.0930(2) 0.4989(2) 0.0487(7) Uani 1 1 d . . . H15A H 0.1989 0.0208 0.5012 0.058 Uiso 1 1 calc R . . C16 C 0.18781(10) 0.1425(2) 0.42578(18) 0.0392(6) Uani 1 1 d . . . H16A H 0.1821 0.1058 0.3768 0.047 Uiso 1 1 calc R . . C17 C 0.18673(8) 0.24810(18) 0.42670(15) 0.0287(5) Uani 1 1 d . . . C18 C 0.17682(7) 0.30910(18) 0.35215(14) 0.0262(4) Uani 1 1 d . . . C19 C 0.17264(8) 0.2729(2) 0.27763(15) 0.0324(5) Uani 1 1 d . . . H19A H 0.1757 0.2022 0.2694 0.039 Uiso 1 1 calc R . . C20 C 0.16376(9) 0.3426(2) 0.21333(15) 0.0355(5) Uani 1 1 d . . . H20A H 0.1613 0.3188 0.1614 0.043 Uiso 1 1 calc R . . C21 C 0.15865(8) 0.4431(2) 0.22436(14) 0.0312(5) Uani 1 1 d . . . H21A H 0.1536 0.4892 0.1806 0.037 Uiso 1 1 calc R . . C22 C 0.16067(7) 0.48037(18) 0.30005(13) 0.0251(4) Uani 1 1 d . . . S3 S 0.11313(2) 0.51629(5) 0.50412(3) 0.03283(14) Uani 1 1 d . . . N5 N 0.07934(6) 0.38366(15) 0.38332(12) 0.0278(4) Uani 1 1 d . . . H5B H 0.0773 0.4369 0.3521 0.033 Uiso 1 1 calc R . . N6 N 0.05066(7) 0.38711(19) 0.22576(13) 0.0366(5) Uani 1 1 d . . . C23 C 0.03449(11) 0.5035(3) 0.11387(17) 0.0526(8) Uani 1 1 d . . . H23A H 0.0038 0.5268 0.1072 0.079 Uiso 1 1 calc R . . H23B H 0.0375 0.5052 0.0611 0.079 Uiso 1 1 calc R . . H23C H 0.0575 0.5483 0.1522 0.079 Uiso 1 1 calc R . . C24 C 0.04152(9) 0.3975(3) 0.14596(17) 0.0439(7) Uani 1 1 d . . . C25 C 0.03910(10) 0.3131(3) 0.0970(2) 0.0587(10) Uani 1 1 d . . . H25A H 0.0330 0.3216 0.0407 0.070 Uiso 1 1 calc R . . C26 C 0.04560(11) 0.2180(3) 0.1308(2) 0.0635(11) Uani 1 1 d . . . H26A H 0.0441 0.1601 0.0979 0.076 Uiso 1 1 calc R . . C27 C 0.05439(10) 0.2056(3) 0.2128(2) 0.0513(8) Uani 1 1 d . . . H27A H 0.0587 0.1402 0.2373 0.062 Uiso 1 1 calc R . . C28 C 0.05665(8) 0.2939(2) 0.25736(17) 0.0373(6) Uani 1 1 d . . . C29 C 0.06800(8) 0.2914(2) 0.34605(17) 0.0349(5) Uani 1 1 d . . . C30 C 0.06863(10) 0.2081(2) 0.3928(2) 0.0460(7) Uani 1 1 d . . . H30A H 0.0616 0.1423 0.3690 0.055 Uiso 1 1 calc R . . C31 C 0.07982(10) 0.2218(2) 0.4764(2) 0.0476(7) Uani 1 1 d . . . H31A H 0.0791 0.1651 0.5090 0.057 Uiso 1 1 calc R . . C32 C 0.09168(9) 0.3152(2) 0.51164(17) 0.0386(6) Uani 1 1 d . . . H32A H 0.0988 0.3231 0.5683 0.046 Uiso 1 1 calc R . . C33 C 0.09350(8) 0.40014(19) 0.46442(14) 0.0292(5) Uani 1 1 d . . . P1 P 0.12100(3) 1.07428(6) 0.72090(5) 0.04654(19) Uani 1 1 d . . . F10 F 0.09850(10) 1.18303(18) 0.7023(2) 0.0952(9) Uani 1 1 d . A . F11 F 0.14132(11) 0.9631(2) 0.73580(19) 0.0998(10) Uani 1 1 d . A . F12 F 0.0871(4) 1.0441(8) 0.7620(6) 0.120(4) Uani 0.574(15) 1 d P A 1 F13 F 0.1545(3) 1.1152(9) 0.7985(8) 0.147(5) Uani 0.574(15) 1 d P A 1 F14 F 0.0811(4) 1.0324(7) 0.6372(5) 0.104(3) Uani 0.574(15) 1 d P A 1 F15 F 0.1496(5) 1.1011(6) 0.6710(11) 0.135(5) Uani 0.574(15) 1 d P A 1 F12' F 0.0770(3) 1.0381(7) 0.7270(14) 0.149(8) Uani 0.426(15) 1 d P A 2 F13' F 0.1419(6) 1.0912(17) 0.8166(7) 0.154(8) Uani 0.426(15) 1 d P A 2 F14' F 0.1091(8) 1.0603(10) 0.6309(4) 0.133(8) Uani 0.426(15) 1 d P A 2 F15' F 0.1710(4) 1.1124(12) 0.7306(11) 0.144(5) Uani 0.426(15) 1 d P A 2 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 Cu1 0.02784(15) 0.02666(15) 0.02478(15) -0.00193(10) 0.00712(11) 0.00208(10) S1 0.0260(3) 0.0398(3) 0.0366(3) -0.0071(3) 0.0025(2) 0.0021(2) N1 0.0270(9) 0.0309(10) 0.0205(9) -0.0004(7) 0.0071(7) -0.0032(7) N2 0.0267(9) 0.0255(9) 0.0276(9) 0.0022(7) 0.0089(8) 0.0018(7) C1 0.0260(11) 0.0598(18) 0.0343(13) 0.0011(12) 0.0035(10) 0.0092(11) C2 0.0278(11) 0.0411(13) 0.0241(11) 0.0027(9) 0.0077(9) -0.0054(9) C3 0.0342(12) 0.0490(16) 0.0264(12) 0.0031(11) 0.0017(10) -0.0121(11) C4 0.0535(16) 0.0407(15) 0.0253(12) -0.0032(10) 0.0068(11) -0.0199(12) C5 0.0538(15) 0.0273(12) 0.0293(12) -0.0025(9) 0.0150(11) -0.0088(11) C6 0.0354(12) 0.0259(11) 0.0227(10) 0.0008(8) 0.0114(9) -0.0048(9) C7 0.0348(12) 0.0276(11) 0.0265(11) 0.0034(9) 0.0128(9) 0.0028(9) C8 0.0556(16) 0.0346(14) 0.0364(14) -0.0041(11) 0.0177(13) 0.0096(12) C9 0.0505(16) 0.0479(17) 0.0482(17) 0.0010(13) 0.0180(14) 0.0231(14) C10 0.0341(13) 0.0495(16) 0.0420(15) 0.0014(12) 0.0111(11) 0.0143(12) C11 0.0283(11) 0.0339(12) 0.0296(12) 0.0031(9) 0.0076(9) 0.0048(9) S2 0.0354(3) 0.0272(3) 0.0270(3) 0.0038(2) 0.0128(2) 0.0020(2) N3 0.0292(9) 0.0335(10) 0.0265(9) 0.0064(8) 0.0114(8) 0.0068(8) N4 0.0248(8) 0.0279(9) 0.0188(8) -0.0004(7) 0.0082(7) 0.0011(7) C12 0.0477(15) 0.0608(19) 0.0261(12) 0.0101(12) 0.0102(11) 0.0126(14) C13 0.0338(12) 0.0452(15) 0.0308(12) 0.0124(11) 0.0150(10) 0.0091(10) C14 0.0478(15) 0.0468(16) 0.0473(16) 0.0231(13) 0.0271(13) 0.0132(12) C15 0.0627(19) 0.0327(14) 0.065(2) 0.0151(13) 0.0399(17) 0.0110(13) C16 0.0487(15) 0.0304(13) 0.0464(15) 0.0024(11) 0.0271(13) 0.0026(11) C17 0.0267(10) 0.0298(11) 0.0324(12) 0.0033(9) 0.0145(9) 0.0040(8) C18 0.0229(10) 0.0292(11) 0.0277(11) -0.0002(9) 0.0111(8) 0.0011(8) C19 0.0335(12) 0.0351(12) 0.0310(12) -0.0042(10) 0.0151(10) 0.0047(10) C20 0.0358(12) 0.0486(15) 0.0246(11) -0.0055(10) 0.0142(10) 0.0031(11) C21 0.0319(11) 0.0423(13) 0.0204(10) 0.0046(9) 0.0113(9) 0.0038(10) C22 0.0214(9) 0.0314(11) 0.0215(10) 0.0027(8) 0.0072(8) -0.0002(8) S3 0.0408(3) 0.0358(3) 0.0222(3) -0.0004(2) 0.0125(2) -0.0022(2) N5 0.0229(9) 0.0309(10) 0.0288(10) 0.0008(8) 0.0091(7) -0.0002(7) N6 0.0242(9) 0.0560(14) 0.0300(11) -0.0102(10) 0.0111(8) -0.0025(9) C23 0.0443(15) 0.088(3) 0.0280(13) -0.0005(14) 0.0167(12) 0.0001(16) C24 0.0257(11) 0.076(2) 0.0310(13) -0.0143(13) 0.0124(10) -0.0054(12) C25 0.0383(15) 0.098(3) 0.0400(16) -0.0285(18) 0.0153(13) -0.0103(16) C26 0.0471(17) 0.082(3) 0.062(2) -0.044(2) 0.0216(16) -0.0096(17) C27 0.0362(14) 0.0568(19) 0.0591(19) -0.0252(15) 0.0163(13) -0.0055(13) C28 0.0221(10) 0.0451(15) 0.0430(14) -0.0160(12) 0.0108(10) -0.0032(10) C29 0.0232(10) 0.0363(13) 0.0443(14) -0.0070(11) 0.0119(10) -0.0006(9) C30 0.0371(14) 0.0318(13) 0.0644(19) -0.0011(13) 0.0145(13) -0.0046(11) C31 0.0374(14) 0.0388(15) 0.0607(19) 0.0159(13) 0.0123(13) -0.0031(11) C32 0.0309(12) 0.0447(15) 0.0369(13) 0.0136(11) 0.0093(10) -0.0015(10) C33 0.0224(10) 0.0360(12) 0.0283(11) 0.0044(9) 0.0088(9) 0.0024(9) P1 0.0522(4) 0.0408(4) 0.0492(4) -0.0015(3) 0.0223(4) 0.0068(3) F10 0.0928(18) 0.0460(13) 0.142(3) -0.0136(14) 0.0399(18) 0.0142(12) F11 0.129(2) 0.0698(16) 0.111(2) 0.0362(15) 0.0586(19) 0.0572(17) F12 0.156(9) 0.133(6) 0.127(6) -0.019(5) 0.117(7) -0.007(6) F13 0.081(5) 0.134(6) 0.138(9) -0.033(7) -0.056(5) -0.002(5) F14 0.142(7) 0.074(4) 0.072(4) -0.028(3) 0.015(4) -0.011(4) F15 0.177(10) 0.093(5) 0.226(13) 0.053(7) 0.177(11) 0.038(6) F12' 0.033(3) 0.059(5) 0.34(2) 0.068(8) 0.055(7) 0.016(3) F13' 0.165(13) 0.25(2) 0.051(4) -0.022(7) 0.048(7) 0.077(12) F14' 0.251(19) 0.076(7) 0.027(3) 0.000(3) 0.006(7) 0.064(9) F15' 0.098(7) 0.220(14) 0.140(11) -0.009(10) 0.072(8) -0.048(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.1064(19) . ? Cu1 N1 2.112(2) . ? Cu1 S2 2.2218(8) . ? Cu1 S3 2.2642(7) . ? S1 C11 1.782(3) . ? S1 S1 2.0297(14) 2 ? N1 C6 1.345(3) . ? N1 C2 1.345(3) . ? N2 C11 1.336(3) . ? N2 C7 1.345(3) . ? C1 C2 1.506(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.391(4) . ? C3 C4 1.379(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(4) . ? C4 H4A 0.9500 . ? C5 C6 1.386(3) . ? C5 H5A 0.9500 . ? C6 C7 1.490(3) . ? C7 C8 1.392(4) . ? C8 C9 1.386(4) . ? C8 H8A 0.9500 . ? C9 C10 1.375(4) . ? C9 H9A 0.9500 . ? C10 C11 1.387(4) . ? C10 H10A 0.9500 . ? S2 C22 1.688(2) . ? N3 C17 1.339(3) . ? N3 C13 1.340(3) . ? N4 C22 1.357(3) . ? N4 C18 1.364(3) . ? N4 H4B 0.8800 . ? C12 C13 1.503(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.390(4) . ? C14 C15 1.375(5) . ? C14 H14A 0.9500 . ? C15 C16 1.379(4) . ? C15 H15A 0.9500 . ? C16 C17 1.387(4) . ? C16 H16A 0.9500 . ? C17 C18 1.476(3) . ? C18 C19 1.366(3) . ? C19 C20 1.407(4) . ? C19 H19A 0.9500 . ? C20 C21 1.353(4) . ? C20 H20A 0.9500 . ? C21 C22 1.411(3) . ? C21 H21A 0.9500 . ? S3 C33 1.695(3) . ? N5 C33 1.353(3) . ? N5 C29 1.362(3) . ? N5 H5B 0.8800 . ? N6 C28 1.330(4) . ? N6 C24 1.342(4) . ? C23 C24 1.488(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.394(5) . ? C25 C26 1.367(6) . ? C25 H25A 0.9500 . ? C26 C27 1.385(5) . ? C26 H26A 0.9500 . ? C27 C28 1.391(4) . ? C27 H27A 0.9500 . ? C28 C29 1.478(4) . ? C29 C30 1.369(4) . ? C30 C31 1.402(5) . ? C30 H30A 0.9500 . ? C31 C32 1.363(4) . ? C31 H31A 0.9500 . ? C32 C33 1.411(3) . ? C32 H32A 0.9500 . ? P1 F13 1.481(8) . ? P1 F14' 1.509(8) . ? P1 F12' 1.513(9) . ? P1 F15 1.531(6) . ? P1 F12 1.563(7) . ? P1 F10 1.573(3) . ? P1 F11 1.576(2) . ? P1 F13' 1.587(11) . ? P1 F15' 1.604(10) . ? P1 F14 1.634(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 77.98(8) . . ? N2 Cu1 S2 110.65(6) . . ? N1 Cu1 S2 117.69(6) . . ? N2 Cu1 S3 103.06(6) . . ? N1 Cu1 S3 97.69(6) . . ? S2 Cu1 S3 134.87(3) . . ? C11 S1 S1 105.65(9) . 2 ? C6 N1 C2 119.8(2) . . ? C6 N1 Cu1 114.89(15) . . ? C2 N1 Cu1 125.09(17) . . ? C11 N2 C7 119.6(2) . . ? C11 N2 Cu1 124.69(17) . . ? C7 N2 Cu1 115.12(15) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.1(2) . . ? N1 C2 C1 117.2(2) . . ? C3 C2 C1 121.7(2) . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5A 120.7 . . ? C6 C5 H5A 120.7 . . ? N1 C6 C5 121.7(2) . . ? N1 C6 C7 115.8(2) . . ? C5 C6 C7 122.5(2) . . ? N2 C7 C8 120.8(2) . . ? N2 C7 C6 115.5(2) . . ? C8 C7 C6 123.7(2) . . ? C9 C8 C7 118.8(3) . . ? C9 C8 H8A 120.6 . . ? C7 C8 H8A 120.6 . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 117.4(3) . . ? C9 C10 H10A 121.3 . . ? C11 C10 H10A 121.3 . . ? N2 C11 C10 122.9(2) . . ? N2 C11 S1 111.27(18) . . ? C10 C11 S1 125.8(2) . . ? C22 S2 Cu1 111.40(8) . . ? C17 N3 C13 118.4(2) . . ? C22 N4 C18 124.85(19) . . ? C22 N4 H4B 117.6 . . ? C18 N4 H4B 117.6 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 121.3(3) . . ? N3 C13 C12 116.4(2) . . ? C14 C13 C12 122.3(2) . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C15 C16 C17 117.2(3) . . ? C15 C16 H16A 121.4 . . ? C17 C16 H16A 121.4 . . ? N3 C17 C16 123.7(2) . . ? N3 C17 C18 114.3(2) . . ? C16 C17 C18 122.0(2) . . ? N4 C18 C19 118.9(2) . . ? N4 C18 C17 114.9(2) . . ? C19 C18 C17 126.2(2) . . ? C18 C19 C20 118.5(2) . . ? C18 C19 H19A 120.8 . . ? C20 C19 H19A 120.8 . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C22 120.8(2) . . ? C20 C21 H21A 119.6 . . ? C22 C21 H21A 119.6 . . ? N4 C22 C21 115.8(2) . . ? N4 C22 S2 122.25(17) . . ? C21 C22 S2 121.95(18) . . ? C33 S3 Cu1 115.94(9) . . ? C33 N5 C29 125.4(2) . . ? C33 N5 H5B 117.3 . . ? C29 N5 H5B 117.3 . . ? C28 N6 C24 118.6(3) . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C24 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N6 C24 C25 121.2(3) . . ? N6 C24 C23 116.1(3) . . ? C25 C24 C23 122.7(3) . . ? C26 C25 C24 119.3(3) . . ? C26 C25 H25A 120.4 . . ? C24 C25 H25A 120.4 . . ? C25 C26 C27 120.4(3) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C26 C27 C28 116.6(4) . . ? C26 C27 H27A 121.7 . . ? C28 C27 H27A 121.7 . . ? N6 C28 C27 123.9(3) . . ? N6 C28 C29 114.1(2) . . ? C27 C28 C29 121.9(3) . . ? N5 C29 C30 118.4(3) . . ? N5 C29 C28 114.2(2) . . ? C30 C29 C28 127.4(3) . . ? C29 C30 C31 118.7(3) . . ? C29 C30 H30A 120.6 . . ? C31 C30 H30A 120.6 . . ? C32 C31 C30 121.1(3) . . ? C32 C31 H31A 119.4 . . ? C30 C31 H31A 119.4 . . ? C31 C32 C33 120.3(3) . . ? C31 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? N5 C33 C32 115.8(2) . . ? N5 C33 S3 120.40(18) . . ? C32 C33 S3 123.8(2) . . ? F13 P1 F14' 146.2(10) . . ? F13 P1 F12' 113.3(9) . . ? F14' P1 F12' 100.2(10) . . ? F13 P1 F15 94.9(7) . . ? F14' P1 F15 51.4(7) . . ? F12' P1 F15 151.4(8) . . ? F13 P1 F12 91.7(7) . . ? F14' P1 F12 121.9(10) . . ? F15 P1 F12 173.2(7) . . ? F13 P1 F10 88.3(5) . . ? F14' P1 F10 88.8(4) . . ? F12' P1 F10 86.9(3) . . ? F15 P1 F10 89.4(3) . . ? F12 P1 F10 89.5(4) . . ? F13 P1 F11 94.6(5) . . ? F14' P1 F11 89.1(4) . . ? F12' P1 F11 91.4(3) . . ? F15 P1 F11 91.0(3) . . ? F12 P1 F11 89.8(4) . . ? F10 P1 F11 177.05(19) . . ? F14' P1 F13' 170.6(10) . . ? F12' P1 F13' 89.0(9) . . ? F15 P1 F13' 119.5(8) . . ? F12 P1 F13' 67.2(7) . . ? F10 P1 F13' 93.8(7) . . ? F11 P1 F13' 88.5(7) . . ? F13 P1 F15' 57.5(6) . . ? F14' P1 F15' 89.2(9) . . ? F12' P1 F15' 170.5(8) . . ? F12 P1 F15' 148.7(6) . . ? F10 P1 F15' 95.0(6) . . ? F11 P1 F15' 87.1(6) . . ? F13' P1 F15' 81.6(7) . . ? F13 P1 F14 175.9(6) . . ? F12' P1 F14 63.3(7) . . ? F15 P1 F14 88.4(6) . . ? F12 P1 F14 84.9(5) . . ? F10 P1 F14 89.2(3) . . ? F11 P1 F14 87.9(4) . . ? F13' P1 F14 151.9(7) . . ? F15' P1 F14 126.0(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.554 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.067 # Attachment 'jp10.cif' data_jp10_173k _database_code_depnum_ccdc_archive 'CCDC 765877' #TrackingRef 'jp10.cif' _audit_creation_date 07-05-17 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '5171828 jp10_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.1500(2) _cell_length_b 9.9823(2) _cell_length_c 24.1761(5) _cell_angle_alpha 90 _cell_angle_beta 95.3134(10) _cell_angle_gamma 90 _cell_volume 1958.41(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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' 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' 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 = C22 H18 N4 S2 # Dc = 1.37 Fooo = 840.00 Mu = 2.87 M = 402.54 # Found Formula = C22 H18 N4 S2 # Dc = 1.37 FOOO = 840.00 Mu = 2.87 M = 402.54 _chemical_formula_sum 'C22 H18 N4 S2' _chemical_formula_moiety 'C22 H18 N4 S2' _chemical_compound_source ? _chemical_formula_weight 402.54 _cell_measurement_reflns_used 7622 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.287 # Sheldrick geometric approximatio 0.97 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 # 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_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _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 173 _diffrn_reflns_number 14776 _reflns_number_total 4667 _diffrn_reflns_av_R_equivalents 0.040 # Number of reflections with Friedels Law is 4667 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4655 _diffrn_reflns_theta_min 2.209 _diffrn_reflns_theta_max 27.910 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.910 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 31 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.15 _refine_ls_number_reflns 2579 _refine_ls_number_restraints 0 _refine_ls_number_parameters 253 #_refine_ls_R_factor_ref 0.0338 _refine_ls_wR_factor_ref 0.0408 _refine_ls_goodness_of_fit_ref 0.9530 #_reflns_number_all 4640 _refine_ls_R_factor_all 0.0703 _refine_ls_wR_factor_all 0.0595 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 2579 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_gt 0.0408 _refine_ls_shift/su_max 0.000428 # 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 . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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^) + ( 0.02P)^2^ + 0.01P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _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_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 Fih. ; ? ; _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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). 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 atomsattached 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 0.74295(7) 0.70475(6) 0.30223(2) 0.0438 1.0000 Uani . . . . . . S2 S 0.80415(7) 0.61604(7) 0.23152(2) 0.0443 1.0000 Uani . . . . . . N1 N 0.7391(2) 0.62432(17) 0.40307(7) 0.0327 1.0000 Uani . . . . . . N2 N 0.7142(2) 0.50618(17) 0.54297(7) 0.0351 1.0000 Uani . . . . . . N3 N 1.0802(2) 0.58058(16) 0.18903(6) 0.0319 1.0000 Uani . . . . . . N4 N 1.4633(2) 0.54834(17) 0.12706(7) 0.0333 1.0000 Uani . . . . . . C1 C 0.7947(3) 0.5840(2) 0.35575(8) 0.0341 1.0000 Uani . . . . . . C2 C 0.8807(3) 0.4665(2) 0.34978(9) 0.0402 1.0000 Uani . . . . . . C3 C 0.9117(3) 0.3869(2) 0.39622(9) 0.0424 1.0000 Uani . . . . . . C4 C 0.8551(3) 0.4254(2) 0.44587(9) 0.0370 1.0000 Uani . . . . . . C5 C 0.7677(2) 0.5447(2) 0.44783(8) 0.0313 1.0000 Uani . . . . . . C6 C 0.6982(2) 0.5904(2) 0.49947(8) 0.0315 1.0000 Uani . . . . . . C7 C 0.6199(3) 0.7131(2) 0.50141(9) 0.0365 1.0000 Uani . . . . . . C8 C 0.5538(3) 0.7497(2) 0.54964(9) 0.0420 1.0000 Uani . . . . . . C9 C 0.5670(3) 0.6634(2) 0.59417(9) 0.0407 1.0000 Uani . . . . . . C10 C 0.6495(3) 0.5427(2) 0.58979(9) 0.0374 1.0000 Uani . . . . . . C11 C 0.6698(3) 0.4466(2) 0.63776(9) 0.0501 1.0000 Uani . . . . . . C21 C 1.0164(3) 0.6558(2) 0.22732(8) 0.0333 1.0000 Uani . . . . . . C22 C 1.1025(3) 0.7543(2) 0.25837(9) 0.0391 1.0000 Uani . . . . . . C23 C 1.2656(3) 0.7731(2) 0.24934(9) 0.0392 1.0000 Uani . . . . . . C24 C 1.3352(3) 0.6975(2) 0.20992(8) 0.0341 1.0000 Uani . . . . . . C25 C 1.2386(3) 0.6029(2) 0.17984(8) 0.0297 1.0000 Uani . . . . . . C26 C 1.3074(3) 0.5201(2) 0.13642(8) 0.0304 1.0000 Uani . . . . . . C27 C 1.2168(3) 0.4193(2) 0.10829(8) 0.0360 1.0000 Uani . . . . . . C28 C 1.2917(3) 0.3444(2) 0.06969(9) 0.0414 1.0000 Uani . . . . . . C29 C 1.4525(3) 0.3718(2) 0.06022(9) 0.0399 1.0000 Uani . . . . . . C30 C 1.5356(3) 0.4754(2) 0.08953(8) 0.0349 1.0000 Uani . . . . . . C31 C 1.7104(3) 0.5096(2) 0.08172(10) 0.0485 1.0000 Uani . . . . . . H21 H 0.9178 0.4430 0.3142 0.0500 1.0000 Uiso R . . . . . H31 H 0.9736 0.3032 0.3941 0.0527 1.0000 Uiso R . . . . . H41 H 0.8765 0.3724 0.4794 0.0463 1.0000 Uiso R . . . . . H71 H 0.6100 0.7705 0.4690 0.0465 1.0000 Uiso R . . . . . H81 H 0.4979 0.8348 0.5519 0.0531 1.0000 Uiso R . . . . . H91 H 0.5192 0.6858 0.6284 0.0483 1.0000 Uiso R . . . . . H111 H 0.6466 0.4919 0.6712 0.0767 1.0000 Uiso R . . . . . H112 H 0.7829 0.4105 0.6418 0.0767 1.0000 Uiso R . . . . . H113 H 0.5885 0.3730 0.6309 0.0765 1.0000 Uiso R . . . . . H221 H 1.0479 0.8052 0.2854 0.0477 1.0000 Uiso R . . . . . H231 H 1.3333 0.8396 0.2707 0.0501 1.0000 Uiso R . . . . . H241 H 1.4515 0.7090 0.2031 0.0422 1.0000 Uiso R . . . . . H271 H 1.1037 0.4009 0.1155 0.0438 1.0000 Uiso R . . . . . H281 H 1.2303 0.2751 0.0498 0.0518 1.0000 Uiso R . . . . . H291 H 1.5058 0.3213 0.0337 0.0488 1.0000 Uiso R . . . . . H311 H 1.7308 0.4924 0.0436 0.0753 1.0000 Uiso R . . . . . H312 H 1.7867 0.4576 0.1065 0.0757 1.0000 Uiso R . . . . . H313 H 1.7310 0.6029 0.0888 0.0758 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 0.0446(4) 0.0537(4) 0.0347(3) 0.0054(3) 0.0122(2) 0.0120(3) S2 0.0363(3) 0.0656(4) 0.0318(3) -0.0026(3) 0.0071(2) -0.0016(3) N1 0.0287(9) 0.0350(10) 0.0353(9) -0.0008(8) 0.0077(7) -0.0008(8) N2 0.0367(10) 0.0366(10) 0.0329(10) -0.0016(8) 0.0076(8) -0.0035(9) N3 0.0339(10) 0.0345(10) 0.0278(9) 0.0028(8) 0.0055(7) -0.0003(8) N4 0.0326(10) 0.0341(10) 0.0339(9) -0.0014(8) 0.0067(8) -0.0003(8) C1 0.0297(11) 0.0398(13) 0.0337(11) 0.0024(9) 0.0078(9) -0.0018(10) C2 0.0421(13) 0.0431(13) 0.0374(12) -0.0042(10) 0.0146(10) 0.0033(11) C3 0.0442(14) 0.0356(13) 0.0497(13) 0.0006(11) 0.0172(11) 0.0078(11) C4 0.0372(12) 0.0357(12) 0.0392(12) 0.0046(10) 0.0098(10) 0.0015(10) C5 0.0273(11) 0.0328(12) 0.0344(11) -0.0019(9) 0.0054(9) -0.0044(10) C6 0.0254(11) 0.0348(12) 0.0343(11) -0.0033(9) 0.0037(9) -0.0063(10) C7 0.0361(12) 0.0352(12) 0.0389(12) -0.0004(10) 0.0075(10) -0.0006(11) C8 0.0403(13) 0.0397(13) 0.0471(14) -0.0085(11) 0.0092(11) 0.0024(11) C9 0.0409(14) 0.0457(14) 0.0371(12) -0.0115(10) 0.0126(10) -0.0079(11) C10 0.0368(13) 0.0421(13) 0.0339(12) -0.0038(10) 0.0062(10) -0.0106(11) C11 0.0628(16) 0.0524(15) 0.0367(13) 0.0008(11) 0.0128(12) -0.0028(13) C21 0.0355(12) 0.0401(12) 0.0247(10) 0.0057(9) 0.0049(9) 0.0026(10) C22 0.0454(14) 0.0409(13) 0.0319(11) -0.0037(10) 0.0084(10) 0.0028(11) C23 0.0448(14) 0.0385(13) 0.0343(11) -0.0039(10) 0.0038(10) -0.0042(11) C24 0.0342(12) 0.0365(12) 0.0316(11) 0.0007(10) 0.0036(9) -0.0040(10) C25 0.0346(12) 0.0294(11) 0.0255(10) 0.0051(9) 0.0046(9) 0.0001(10) C26 0.0333(12) 0.0296(11) 0.0284(10) 0.0045(9) 0.0034(9) 0.0007(10) C27 0.0365(12) 0.0373(12) 0.0344(11) -0.0008(10) 0.0051(10) -0.0042(10) C28 0.0454(14) 0.0409(13) 0.0384(12) -0.0095(10) 0.0062(10) -0.0068(11) C29 0.0441(14) 0.0389(13) 0.0377(12) -0.0074(10) 0.0098(10) -0.0002(11) C30 0.0345(12) 0.0364(12) 0.0346(11) 0.0012(9) 0.0069(9) 0.0029(10) C31 0.0399(14) 0.0552(16) 0.0524(15) -0.0110(12) 0.0154(11) -0.0041(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3217(5) 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 . S2 . 2.0281(8) yes S1 . C1 . 1.790(2) yes S2 . C21 . 1.787(2) yes N1 . C1 . 1.331(2) yes N1 . C5 . 1.345(2) yes N2 . C6 . 1.343(2) yes N2 . C10 . 1.343(3) yes N3 . C21 . 1.334(3) yes N3 . C25 . 1.349(3) yes N4 . C26 . 1.341(3) yes N4 . C30 . 1.341(3) yes C1 . C2 . 1.381(3) yes C2 . C3 . 1.380(3) yes C2 . H21 . 0.968 no C3 . C4 . 1.380(3) yes C3 . H31 . 0.980 no C4 . C5 . 1.391(3) yes C4 . H41 . 0.971 no C5 . C6 . 1.489(3) yes C6 . C7 . 1.384(3) yes C7 . C8 . 1.378(3) yes C7 . H71 . 0.968 no C8 . C9 . 1.375(3) yes C8 . H81 . 0.968 no C9 . C10 . 1.389(3) yes C9 . H91 . 0.973 no C10 . C11 . 1.502(3) yes C11 . H111 . 0.961 no C11 . H112 . 0.986 no C11 . H113 . 0.993 no C21 . C22 . 1.387(3) yes C22 . C23 . 1.380(3) yes C22 . H221 . 0.969 no C23 . C24 . 1.378(3) yes C23 . H231 . 0.979 no C24 . C25 . 1.391(3) yes C24 . H241 . 0.983 no C25 . C26 . 1.486(3) yes C26 . C27 . 1.389(3) yes C27 . C28 . 1.381(3) yes C27 . H271 . 0.971 no C28 . C29 . 1.379(3) yes C28 . H281 . 0.957 no C29 . C30 . 1.393(3) yes C29 . H291 . 0.952 no C30 . C31 . 1.494(3) yes C31 . H311 . 0.968 no C31 . H312 . 0.973 no C31 . H313 . 0.959 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 S2 . S1 . C1 . 104.80(8) yes S1 . S2 . C21 . 105.42(7) yes C1 . N1 . C5 . 117.73(18) yes C6 . N2 . C10 . 118.22(18) yes C21 . N3 . C25 . 117.51(17) yes C26 . N4 . C30 . 118.83(18) yes S1 . C1 . N1 . 109.96(15) yes S1 . C1 . C2 . 125.74(16) yes N1 . C1 . C2 . 124.29(19) yes C1 . C2 . C3 . 117.4(2) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 122.4 no C2 . C3 . C4 . 119.8(2) yes C2 . C3 . H31 . 120.3 no C4 . C3 . H31 . 119.9 no C3 . C4 . C5 . 118.8(2) yes C3 . C4 . H41 . 121.8 no C5 . C4 . H41 . 119.4 no C4 . C5 . N1 . 121.95(19) yes C4 . C5 . C6 . 121.77(19) yes N1 . C5 . C6 . 116.27(18) yes C5 . C6 . N2 . 116.60(18) yes C5 . C6 . C7 . 120.77(19) yes N2 . C6 . C7 . 122.63(19) yes C6 . C7 . C8 . 118.7(2) yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 121.2 no C7 . C8 . C9 . 119.2(2) yes C7 . C8 . H81 . 120.3 no C9 . C8 . H81 . 120.5 no C8 . C9 . C10 . 119.1(2) yes C8 . C9 . H91 . 120.9 no C10 . C9 . H91 . 119.9 no C9 . C10 . N2 . 122.0(2) yes C9 . C10 . C11 . 121.0(2) yes N2 . C10 . C11 . 117.0(2) yes C10 . C11 . H111 . 109.5 no C10 . C11 . H112 . 110.2 no H111 . C11 . H112 . 110.1 no C10 . C11 . H113 . 108.6 no H111 . C11 . H113 . 108.0 no H112 . C11 . H113 . 110.4 no S2 . C21 . N3 . 110.85(15) yes S2 . C21 . C22 . 124.78(17) yes N3 . C21 . C22 . 124.3(2) yes C21 . C22 . C23 . 117.2(2) yes C21 . C22 . H221 . 119.8 no C23 . C22 . H221 . 123.0 no C22 . C23 . C24 . 119.9(2) yes C22 . C23 . H231 . 120.9 no C24 . C23 . H231 . 119.2 no C23 . C24 . C25 . 118.9(2) yes C23 . C24 . H241 . 121.1 no C25 . C24 . H241 . 120.0 no C24 . C25 . N3 . 122.02(18) yes C24 . C25 . C26 . 120.97(19) yes N3 . C25 . C26 . 117.01(18) yes C25 . C26 . N4 . 115.33(18) yes C25 . C26 . C27 . 122.03(19) yes N4 . C26 . C27 . 122.63(19) yes C26 . C27 . C28 . 118.3(2) yes C26 . C27 . H271 . 121.3 no C28 . C27 . H271 . 120.4 no C27 . C28 . C29 . 119.4(2) yes C27 . C28 . H281 . 119.2 no C29 . C28 . H281 . 121.4 no C28 . C29 . C30 . 119.2(2) yes C28 . C29 . H291 . 120.5 no C30 . C29 . H291 . 120.4 no C29 . C30 . N4 . 121.59(19) yes C29 . C30 . C31 . 121.98(19) yes N4 . C30 . C31 . 116.42(19) yes C30 . C31 . H311 . 109.3 no C30 . C31 . H312 . 111.3 no H311 . C31 . H312 . 109.6 no C30 . C31 . H313 . 110.7 no H311 . C31 . H313 . 107.4 no H312 . C31 . H313 . 108.5 no # Attachment 'jp12.cif' data_jp12-1_173k _database_code_depnum_ccdc_archive 'CCDC 765878' #TrackingRef 'jp12.cif' _audit_creation_date 07-05-29 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '5271543 jp12-1_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.1160(5) _cell_length_b 15.6202(4) _cell_length_c 15.8881(5) _cell_angle_alpha 64.7657(19) _cell_angle_beta 74.9436(17) _cell_angle_gamma 82.340(2) _cell_volume 2842.41(17) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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' 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' 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' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 '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' 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' 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' _cell_formula_units_Z 2 # Given Formula = C44 H36 Cu4 F12 N8 O4 P2 S4 # Dc = 1.65 Fooo = 1424.00 Mu = 17.66 M = 1413.19 # Found Formula = C46 H42 Cu2 F12 N10 O4 P2 S6 # Dc = 1.65 FOOO = 1424.00 Mu = 11.17 M = 1408.32 _chemical_formula_sum 'C46 H42 Cu2 F12 N10 O4 P2 S6' _chemical_formula_moiety 'C44 H36 Cu2 N8 S6, 2(F6 P), 2(C H3 N O2)' _chemical_compound_source ? _chemical_formula_weight 1408.32 _cell_measurement_reflns_used 11415 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_max 0.29 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.117 # Sheldrick geometric approximatio 0.96 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 # 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_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _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 173 _diffrn_reflns_number 22843 _reflns_number_total 12869 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 12869 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 13017 _diffrn_reflns_theta_min 1.971 _diffrn_reflns_theta_max 27.468 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.820 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -16 _reflns_limit_h_max 17 _reflns_limit_k_min -17 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.50 _refine_diff_density_max 0.70 _refine_ls_number_reflns 8154 _refine_ls_number_restraints 0 _refine_ls_number_parameters 739 #_refine_ls_R_factor_ref 0.0673 _refine_ls_wR_factor_ref 0.0518 _refine_ls_goodness_of_fit_ref 0.9867 #_reflns_number_all 12780 _refine_ls_R_factor_all 0.1210 _refine_ls_wR_factor_all 0.0928 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.0\s(I) _reflns_number_gt 8154 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_gt 0.0518 _refine_ls_shift/su_max 0.000561 # 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 . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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^) + ( 0.01P)^2^ + 0.03P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _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_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 Fih. ; ? ; _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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). 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 atomsattached 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 Cu1 Cu 0.75235(5) 0.37242(4) 0.72593(4) 0.0394 1.0000 Uani . . . . . . Cu2 Cu 1.31247(4) 0.07774(4) 0.73837(4) 0.0359 1.0000 Uani . . . . . . N1 N 0.7847(3) 0.2869(2) 0.8535(2) 0.0346 1.0000 Uani . . . . . . N2 N 0.7120(3) 0.4640(2) 0.7895(3) 0.0353 1.0000 Uani . . . . . . C1 C 0.8331(4) 0.2013(3) 0.8767(3) 0.0349 1.0000 Uani . . . . . . C2 C 0.8657(4) 0.1537(3) 0.9616(3) 0.0423 1.0000 Uani . . . . . . C3 C 0.8487(4) 0.1968(3) 1.0234(3) 0.0492 1.0000 Uani . . . . . . C4 C 0.7986(4) 0.2841(3) 1.0014(3) 0.0457 1.0000 Uani . . . . . . C5 C 0.7672(4) 0.3282(3) 0.9154(3) 0.0358 1.0000 Uani . . . . . . C6 C 0.7145(4) 0.4234(3) 0.8832(3) 0.0384 1.0000 Uani . . . . . . C7 C 0.6704(4) 0.4672(3) 0.9436(4) 0.0503 1.0000 Uani . . . . . . C8 C 0.6245(5) 0.5560(4) 0.9075(4) 0.0571 1.0000 Uani . . . . . . C9 C 0.6244(4) 0.5983(3) 0.8128(4) 0.0513 1.0000 Uani . . . . . . C10 C 0.6685(4) 0.5521(3) 0.7539(3) 0.0413 1.0000 Uani . . . . . . C11 C 0.6693(4) 0.5958(3) 0.6497(3) 0.0550 1.0000 Uani . . . . . . S1 S 0.84495(10) 0.15991(8) 0.78613(8) 0.0407 1.0000 Uani . . . . . . S2 S 0.90877(10) 0.02603(8) 0.83746(9) 0.0414 1.0000 Uani . . . . . . S3 S 1.06792(10) 0.04203(8) 0.80878(8) 0.0402 1.0000 Uani . . . . . . N3 N 1.2178(3) 0.0743(2) 0.6593(2) 0.0291 1.0000 Uani . . . . . . N4 N 1.4223(3) 0.1050(2) 0.6146(2) 0.0317 1.0000 Uani . . . . . . C21 C 1.1140(4) 0.0634(3) 0.6862(3) 0.0333 1.0000 Uani . . . . . . C22 C 1.0526(4) 0.0698(3) 0.6248(3) 0.0437 1.0000 Uani . . . . . . C23 C 1.1024(4) 0.0886(3) 0.5316(4) 0.0494 1.0000 Uani . . . . . . C24 C 1.2093(4) 0.1012(3) 0.5019(3) 0.0457 1.0000 Uani . . . . . . C25 C 1.2659(4) 0.0947(3) 0.5670(3) 0.0361 1.0000 Uani . . . . . . C26 C 1.3823(4) 0.1094(3) 0.5423(3) 0.0366 1.0000 Uani . . . . . . C27 C 1.4444(4) 0.1275(3) 0.4522(3) 0.0488 1.0000 Uani . . . . . . C28 C 1.5507(5) 0.1406(4) 0.4362(4) 0.0604 1.0000 Uani . . . . . . C29 C 1.5923(4) 0.1355(3) 0.5090(4) 0.0508 1.0000 Uani . . . . . . C30 C 1.5253(4) 0.1184(3) 0.5979(3) 0.0388 1.0000 Uani . . . . . . C31 C 1.5664(4) 0.1137(3) 0.6796(3) 0.0450 1.0000 Uani . . . . . . N5 N 0.8478(3) 0.3741(2) 0.6049(2) 0.0323 1.0000 Uani . . . . . . N6 N 0.6426(3) 0.3573(2) 0.6632(3) 0.0370 1.0000 Uani . . . . . . C41 C 0.9531(4) 0.3747(3) 0.5858(3) 0.0382 1.0000 Uani . . . . . . C42 C 1.0172(4) 0.3542(3) 0.5121(3) 0.0485 1.0000 Uani . . . . . . C43 C 0.9684(5) 0.3345(3) 0.4552(3) 0.0544 1.0000 Uani . . . . . . C44 C 0.8596(5) 0.3353(3) 0.4732(3) 0.0446 1.0000 Uani . . . . . . C45 C 0.8017(4) 0.3559(3) 0.5484(3) 0.0362 1.0000 Uani . . . . . . C46 C 0.6847(4) 0.3598(3) 0.5746(3) 0.0401 1.0000 Uani . . . . . . C47 C 0.6211(5) 0.3688(3) 0.5137(4) 0.0513 1.0000 Uani . . . . . . C48 C 0.5143(5) 0.3756(4) 0.5435(4) 0.0644 1.0000 Uani . . . . . . C49 C 0.4705(4) 0.3731(3) 0.6333(4) 0.0554 1.0000 Uani . . . . . . C50 C 0.5368(4) 0.3623(3) 0.6931(4) 0.0440 1.0000 Uani . . . . . . C51 C 0.4947(4) 0.3554(3) 0.7920(4) 0.0536 1.0000 Uani . . . . . . S4 S 0.99506(10) 0.40215(8) 0.66898(9) 0.0439 1.0000 Uani . . . . . . S5 S 1.15384(10) 0.41954(8) 0.61702(9) 0.0442 1.0000 Uani . . . . . . S6 S 1.21814(10) 0.28590(8) 0.65511(8) 0.0404 1.0000 Uani . . . . . . N7 N 1.2727(3) 0.1644(2) 0.8073(2) 0.0317 1.0000 Uani . . . . . . N8 N 1.3485(3) -0.0106(2) 0.8633(2) 0.0298 1.0000 Uani . . . . . . C61 C 1.2262(4) 0.2498(3) 0.7761(3) 0.0367 1.0000 Uani . . . . . . C62 C 1.1892(4) 0.3000(3) 0.8308(3) 0.0457 1.0000 Uani . . . . . . C63 C 1.2027(4) 0.2599(3) 0.9236(3) 0.0506 1.0000 Uani . . . . . . C64 C 1.2517(4) 0.1704(3) 0.9579(3) 0.0456 1.0000 Uani . . . . . . C65 C 1.2842(4) 0.1243(3) 0.8985(3) 0.0328 1.0000 Uani . . . . . . C66 C 1.3343(3) 0.0278(3) 0.9280(3) 0.0318 1.0000 Uani . . . . . . C67 C 1.3648(4) -0.0193(3) 1.0139(3) 0.0383 1.0000 Uani . . . . . . C68 C 1.4124(4) -0.1073(3) 1.0335(3) 0.0419 1.0000 Uani . . . . . . C69 C 1.4281(4) -0.1470(3) 0.9686(3) 0.0403 1.0000 Uani . . . . . . C70 C 1.3946(4) -0.0978(3) 0.8839(3) 0.0346 1.0000 Uani . . . . . . C71 C 1.4065(4) -0.1372(3) 0.8110(3) 0.0422 1.0000 Uani . . . . . . N9 N 1.0415(4) 0.4839(4) 0.1393(4) 0.0739 1.0000 Uani . . . . . . O1 O 1.0311(5) 0.4473(4) 0.2249(4) 0.1303 1.0000 Uani . . . . . . O2 O 1.0155(4) 0.5646(3) 0.0943(4) 0.0980 1.0000 Uani . . . . . . C81 C 1.0894(5) 0.4261(4) 0.0861(4) 0.0725 1.0000 Uani . . . . . . N10 N 0.8644(5) 0.1582(3) 0.3374(5) 0.0745 1.0000 Uani . . . . . . O3 O 0.8655(4) 0.1474(3) 0.4185(4) 0.0983 1.0000 Uani . . . . . . O4 O 0.7978(4) 0.1281(3) 0.3176(4) 0.1001 1.0000 Uani . . . . . . C82 C 0.9485(5) 0.2109(5) 0.2626(5) 0.0995 1.0000 Uani . . . . . . P1 P 0.74433(11) -0.15141(9) 0.77978(9) 0.0436 1.0000 Uani . . . . . . F1 F 0.6635(3) -0.2248(2) 0.8647(2) 0.0801 1.0000 Uani . . . . . . F2 F 0.8252(2) -0.0780(2) 0.6958(2) 0.0653 1.0000 Uani . . . . . . F3 F 0.6994(2) -0.07412(19) 0.82211(19) 0.0575 1.0000 Uani . . . . . . F4 F 0.6597(2) -0.1166(2) 0.7155(2) 0.0720 1.0000 Uani . . . . . . F5 F 0.7893(3) -0.2282(2) 0.7378(2) 0.0680 1.0000 Uani . . . . . . F6 F 0.8289(2) -0.1856(2) 0.8445(2) 0.0648 1.0000 Uani . . . . . . P2 P 0.70336(12) 0.41250(9) 0.22081(9) 0.0478 1.0000 Uani . . . . . . F7 F 0.5919(3) 0.4151(3) 0.2889(2) 0.0998 1.0000 Uani . . . . . . F8 F 0.8111(3) 0.4047(3) 0.1514(2) 0.1004 1.0000 Uani . . . . . . F9 F 0.6677(4) 0.4973(2) 0.1336(2) 0.1075 1.0000 Uani . . . . . . F10 F 0.6593(3) 0.3400(3) 0.1938(3) 0.1006 1.0000 Uani . . . . . . F11 F 0.7377(3) 0.32605(19) 0.30804(19) 0.0660 1.0000 Uani . . . . . . F12 F 0.7437(4) 0.4822(2) 0.2489(3) 0.1260 1.0000 Uani . . . . . . H21 H 0.8981 0.0947 0.9750 0.0509 1.0000 Uiso R . . . . . H31 H 0.8706 0.1664 1.0808 0.0597 1.0000 Uiso R . . . . . H41 H 0.7847 0.3137 1.0433 0.0568 1.0000 Uiso R . . . . . H71 H 0.6710 0.4373 1.0078 0.0633 1.0000 Uiso R . . . . . H81 H 0.5939 0.5861 0.9475 0.0716 1.0000 Uiso R . . . . . H91 H 0.5947 0.6584 0.7865 0.0639 1.0000 Uiso R . . . . . H111 H 0.6694 0.6623 0.6256 0.0794 1.0000 Uiso R . . . . . H112 H 0.7299 0.5752 0.6150 0.0792 1.0000 Uiso R . . . . . H113 H 0.6083 0.5770 0.6407 0.0795 1.0000 Uiso R . . . . . H221 H 0.9807 0.0622 0.6454 0.0547 1.0000 Uiso R . . . . . H231 H 1.0637 0.0927 0.4885 0.0646 1.0000 Uiso R . . . . . H241 H 1.2451 0.1143 0.4390 0.0568 1.0000 Uiso R . . . . . H271 H 1.4153 0.1306 0.4027 0.0615 1.0000 Uiso R . . . . . H281 H 1.5938 0.1519 0.3771 0.0730 1.0000 Uiso R . . . . . H291 H 1.6632 0.1435 0.4997 0.0629 1.0000 Uiso R . . . . . H311 H 1.6351 0.1366 0.6596 0.0682 1.0000 Uiso R . . . . . H312 H 1.5207 0.1516 0.7092 0.0679 1.0000 Uiso R . . . . . H313 H 1.5653 0.0500 0.7275 0.0679 1.0000 Uiso R . . . . . H421 H 1.0911 0.3543 0.5008 0.0573 1.0000 Uiso R . . . . . H431 H 1.0097 0.3204 0.4041 0.0662 1.0000 Uiso R . . . . . H441 H 0.8264 0.3230 0.4356 0.0568 1.0000 Uiso R . . . . . H471 H 0.6513 0.3709 0.4534 0.0660 1.0000 Uiso R . . . . . H481 H 0.4715 0.3821 0.5029 0.0791 1.0000 Uiso R . . . . . H491 H 0.3983 0.3781 0.6545 0.0650 1.0000 Uiso R . . . . . H511 H 0.4291 0.3258 0.8168 0.0796 1.0000 Uiso R . . . . . H512 H 0.4862 0.4169 0.7915 0.0791 1.0000 Uiso R . . . . . H513 H 0.5424 0.3199 0.8312 0.0790 1.0000 Uiso R . . . . . H621 H 1.1569 0.3581 0.8072 0.0572 1.0000 Uiso R . . . . . H631 H 1.1801 0.2924 0.9632 0.0629 1.0000 Uiso R . . . . . H641 H 1.2619 0.1435 1.0192 0.0554 1.0000 Uiso R . . . . . H671 H 1.3530 0.0064 1.0583 0.0477 1.0000 Uiso R . . . . . H681 H 1.4327 -0.1400 1.0919 0.0488 1.0000 Uiso R . . . . . H691 H 1.4606 -0.2051 0.9806 0.0458 1.0000 Uiso R . . . . . H711 H 1.4260 -0.2019 0.8367 0.0653 1.0000 Uiso R . . . . . H712 H 1.4576 -0.1036 0.7545 0.0652 1.0000 Uiso R . . . . . H713 H 1.3404 -0.1319 0.7939 0.0649 1.0000 Uiso R . . . . . H811 H 1.1349 0.4654 0.0270 0.1091 1.0000 Uiso R . . . . . H812 H 1.1292 0.3741 0.1247 0.1092 1.0000 Uiso R . . . . . H813 H 1.0340 0.4034 0.0715 0.1093 1.0000 Uiso R . . . . . H821 H 0.9407 0.2112 0.2037 0.1365 1.0000 Uiso R . . . . . H822 H 1.0131 0.1820 0.2768 0.1366 1.0000 Uiso R . . . . . H823 H 0.9454 0.2738 0.2589 0.1364 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 Cu1 0.0471(4) 0.0453(3) 0.0320(3) -0.0198(3) -0.0165(3) 0.0077(3) Cu2 0.0414(4) 0.0432(3) 0.0273(3) -0.0177(3) -0.0104(3) 0.0020(3) N1 0.040(2) 0.035(2) 0.031(2) -0.0137(17) -0.0115(18) -0.0022(18) N2 0.039(2) 0.037(2) 0.033(2) -0.0165(17) -0.0115(18) 0.0007(17) C1 0.034(3) 0.037(3) 0.033(3) -0.013(2) -0.006(2) -0.005(2) C2 0.048(3) 0.041(3) 0.039(3) -0.014(2) -0.018(2) 0.008(2) C3 0.064(4) 0.048(3) 0.037(3) -0.013(2) -0.022(3) -0.002(3) C4 0.061(4) 0.048(3) 0.034(3) -0.017(2) -0.017(3) -0.005(3) C5 0.039(3) 0.040(3) 0.031(3) -0.014(2) -0.012(2) -0.004(2) C6 0.046(3) 0.038(3) 0.040(3) -0.020(2) -0.014(2) -0.004(2) C7 0.064(4) 0.050(3) 0.044(3) -0.024(3) -0.014(3) -0.002(3) C8 0.074(4) 0.050(3) 0.057(4) -0.034(3) -0.012(3) 0.006(3) C9 0.058(4) 0.040(3) 0.062(4) -0.028(3) -0.018(3) 0.011(2) C10 0.044(3) 0.036(3) 0.043(3) -0.015(2) -0.012(2) -0.002(2) C11 0.064(4) 0.048(3) 0.047(3) -0.011(3) -0.020(3) 0.010(3) S1 0.0467(8) 0.0401(6) 0.0376(7) -0.0190(5) -0.0123(6) 0.0077(6) S2 0.0395(8) 0.0339(6) 0.0464(7) -0.0151(6) -0.0039(6) -0.0029(5) S3 0.0379(8) 0.0481(7) 0.0330(6) -0.0166(5) -0.0075(6) 0.0027(6) N3 0.033(2) 0.0313(19) 0.027(2) -0.0148(16) -0.0077(17) -0.0019(16) N4 0.031(2) 0.036(2) 0.030(2) -0.0158(16) -0.0067(17) -0.0001(16) C21 0.034(3) 0.038(2) 0.031(2) -0.017(2) -0.010(2) 0.002(2) C22 0.036(3) 0.057(3) 0.044(3) -0.025(2) -0.012(2) 0.000(2) C23 0.046(4) 0.070(3) 0.045(3) -0.032(3) -0.018(3) 0.000(3) C24 0.054(4) 0.061(3) 0.028(3) -0.023(2) -0.010(2) -0.002(3) C25 0.049(3) 0.037(2) 0.027(2) -0.016(2) -0.011(2) 0.000(2) C26 0.042(3) 0.038(3) 0.033(3) -0.017(2) -0.006(2) -0.005(2) C27 0.047(4) 0.071(3) 0.037(3) -0.030(3) -0.005(3) -0.013(3) C28 0.058(4) 0.087(4) 0.039(3) -0.033(3) 0.007(3) -0.018(3) C29 0.041(3) 0.069(3) 0.048(3) -0.032(3) 0.001(3) -0.009(3) C30 0.047(3) 0.035(2) 0.039(3) -0.018(2) -0.013(2) 0.000(2) C31 0.040(3) 0.048(3) 0.047(3) -0.019(2) -0.012(2) -0.001(2) N5 0.041(3) 0.034(2) 0.026(2) -0.0127(16) -0.0141(18) 0.0018(17) N6 0.044(3) 0.033(2) 0.037(2) -0.0143(17) -0.017(2) 0.0010(18) C41 0.053(4) 0.031(2) 0.031(3) -0.011(2) -0.016(2) 0.004(2) C42 0.051(4) 0.057(3) 0.038(3) -0.021(2) -0.010(3) 0.000(3) C43 0.072(5) 0.061(3) 0.033(3) -0.026(3) -0.007(3) 0.001(3) C44 0.066(4) 0.042(3) 0.034(3) -0.018(2) -0.020(3) -0.002(3) C45 0.050(3) 0.030(2) 0.029(3) -0.009(2) -0.013(2) -0.002(2) C46 0.056(4) 0.028(2) 0.041(3) -0.012(2) -0.025(3) 0.001(2) C47 0.063(4) 0.057(3) 0.046(3) -0.023(3) -0.027(3) -0.004(3) C48 0.063(5) 0.070(4) 0.065(4) -0.016(3) -0.040(4) -0.006(3) C49 0.047(4) 0.055(3) 0.061(4) -0.013(3) -0.024(3) -0.005(3) C50 0.051(4) 0.029(2) 0.050(3) -0.010(2) -0.020(3) 0.000(2) C51 0.044(3) 0.054(3) 0.061(4) -0.022(3) -0.014(3) 0.005(2) S4 0.0457(8) 0.0518(7) 0.0420(7) -0.0240(6) -0.0166(6) 0.0029(6) S5 0.0488(8) 0.0317(6) 0.0459(7) -0.0062(5) -0.0162(6) -0.0044(5) S6 0.0492(8) 0.0383(6) 0.0339(7) -0.0122(5) -0.0155(6) 0.0017(6) N7 0.034(2) 0.032(2) 0.029(2) -0.0118(16) -0.0090(17) -0.0003(17) N8 0.034(2) 0.032(2) 0.0256(19) -0.0136(16) -0.0059(17) -0.0036(16) C61 0.042(3) 0.036(3) 0.031(3) -0.011(2) -0.008(2) -0.006(2) C62 0.064(4) 0.039(3) 0.041(3) -0.021(2) -0.020(3) 0.009(2) C63 0.075(4) 0.042(3) 0.041(3) -0.027(2) -0.009(3) 0.007(3) C64 0.066(4) 0.047(3) 0.028(2) -0.019(2) -0.013(2) 0.004(3) C65 0.038(3) 0.036(2) 0.028(2) -0.017(2) -0.005(2) -0.005(2) C66 0.035(3) 0.034(2) 0.028(2) -0.012(2) -0.009(2) -0.004(2) C67 0.045(3) 0.043(3) 0.031(3) -0.016(2) -0.011(2) -0.008(2) C68 0.046(3) 0.043(3) 0.034(3) -0.010(2) -0.016(2) 0.001(2) C69 0.044(3) 0.034(2) 0.038(3) -0.011(2) -0.010(2) 0.004(2) C70 0.034(3) 0.034(2) 0.035(3) -0.014(2) -0.005(2) -0.004(2) C71 0.048(3) 0.044(3) 0.038(3) -0.025(2) -0.004(2) 0.002(2) N9 0.079(4) 0.083(4) 0.072(4) -0.040(3) -0.013(3) -0.020(3) O1 0.185(6) 0.157(5) 0.067(4) -0.061(4) -0.023(4) -0.019(4) O2 0.092(4) 0.068(3) 0.131(4) -0.046(3) -0.011(3) -0.006(3) C81 0.076(5) 0.074(4) 0.068(4) -0.033(3) -0.011(3) 0.005(3) N10 0.066(4) 0.060(3) 0.114(5) -0.053(4) -0.026(4) 0.015(3) O3 0.105(4) 0.093(3) 0.106(4) -0.052(3) -0.024(3) 0.005(3) O4 0.073(3) 0.076(3) 0.192(5) -0.084(3) -0.052(3) 0.011(2) C82 0.045(4) 0.107(5) 0.118(6) -0.038(5) 0.011(4) 0.000(4) P1 0.0474(9) 0.0567(8) 0.0366(7) -0.0272(6) -0.0130(6) 0.0020(6) F1 0.089(3) 0.082(2) 0.065(2) -0.0362(18) 0.0151(18) -0.0293(19) F2 0.069(2) 0.075(2) 0.0487(18) -0.0227(16) -0.0050(16) -0.0154(16) F3 0.075(2) 0.0661(18) 0.0481(17) -0.0382(15) -0.0291(16) 0.0246(15) F4 0.050(2) 0.133(3) 0.059(2) -0.062(2) -0.0277(16) 0.0188(18) F5 0.083(2) 0.076(2) 0.064(2) -0.0517(17) -0.0117(18) 0.0055(17) F6 0.066(2) 0.092(2) 0.0489(18) -0.0413(16) -0.0295(16) 0.0310(17) P2 0.0672(11) 0.0457(7) 0.0351(7) -0.0207(6) -0.0156(7) 0.0062(7) F7 0.078(3) 0.134(3) 0.070(2) -0.038(2) -0.014(2) 0.032(2) F8 0.082(3) 0.129(3) 0.061(2) -0.029(2) 0.007(2) 0.013(2) F9 0.188(4) 0.081(2) 0.048(2) -0.0299(18) -0.043(2) 0.062(2) F10 0.151(4) 0.097(3) 0.082(3) -0.047(2) -0.046(3) -0.020(2) F11 0.092(3) 0.0621(18) 0.0432(17) -0.0206(14) -0.0261(17) 0.0205(16) F12 0.229(5) 0.077(2) 0.101(3) -0.034(2) -0.065(3) -0.054(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.16241(19) 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 Cu1 . N1 . 2.015(3) yes Cu1 . N2 . 2.024(4) yes Cu1 . N5 . 1.995(4) yes Cu1 . N6 . 2.039(4) yes Cu2 . N3 . 2.002(3) yes Cu2 . N4 . 2.025(4) yes Cu2 . N7 . 2.020(4) yes Cu2 . N8 . 2.011(3) yes N1 . C1 . 1.344(5) yes N1 . C5 . 1.348(5) yes N2 . C6 . 1.355(5) yes N2 . C10 . 1.354(5) yes C1 . C2 . 1.383(6) yes C1 . S1 . 1.779(5) yes C2 . C3 . 1.370(6) yes C2 . H21 . 0.921 no C3 . C4 . 1.373(7) yes C3 . H31 . 0.933 no C4 . C5 . 1.389(6) yes C4 . H41 . 0.931 no C5 . C6 . 1.487(6) yes C6 . C7 . 1.374(6) yes C7 . C8 . 1.377(7) yes C7 . H71 . 0.925 no C8 . C9 . 1.362(7) yes C8 . H81 . 0.925 no C9 . C10 . 1.384(7) yes C9 . H91 . 0.927 no C10 . C11 . 1.496(6) yes C11 . H111 . 0.942 no C11 . H112 . 0.946 no C11 . H113 . 0.950 no S1 . S2 . 2.0427(16) yes S2 . S3 . 2.0434(17) yes S3 . C21 . 1.777(4) yes N3 . C21 . 1.328(5) yes N3 . C25 . 1.350(5) yes N4 . C26 . 1.355(5) yes N4 . C30 . 1.335(6) yes C21 . C22 . 1.384(6) yes C22 . C23 . 1.372(6) yes C22 . H221 . 0.920 no C23 . C24 . 1.371(7) yes C23 . H231 . 0.931 no C24 . C25 . 1.386(6) yes C24 . H241 . 0.932 no C25 . C26 . 1.497(6) yes C26 . C27 . 1.379(6) yes C27 . C28 . 1.377(7) yes C27 . H271 . 0.941 no C28 . C29 . 1.372(7) yes C28 . H281 . 0.918 no C29 . C30 . 1.391(6) yes C29 . H291 . 0.920 no C30 . C31 . 1.501(6) yes C31 . H311 . 0.938 no C31 . H312 . 0.963 no C31 . H313 . 0.961 no N5 . C41 . 1.335(6) yes N5 . C45 . 1.341(5) yes N6 . C46 . 1.356(6) yes N6 . C50 . 1.349(6) yes C41 . C42 . 1.385(7) yes C41 . S4 . 1.776(5) yes C42 . C43 . 1.384(7) yes C42 . H421 . 0.939 no C43 . C44 . 1.380(7) yes C43 . H431 . 0.944 no C44 . C45 . 1.378(6) yes C44 . H441 . 0.914 no C45 . C46 . 1.483(7) yes C46 . C47 . 1.388(6) yes C47 . C48 . 1.363(7) yes C47 . H471 . 0.924 no C48 . C49 . 1.379(8) yes C48 . H481 . 0.926 no C49 . C50 . 1.393(7) yes C49 . H491 . 0.924 no C50 . C51 . 1.485(7) yes C51 . H511 . 0.940 no C51 . H512 . 0.949 no C51 . H513 . 0.950 no S4 . S5 . 2.0392(19) yes S5 . S6 . 2.0381(16) yes S6 . C61 . 1.786(4) yes N7 . C61 . 1.331(5) yes N7 . C65 . 1.352(5) yes N8 . C66 . 1.359(5) yes N8 . C70 . 1.353(5) yes C61 . C62 . 1.367(6) yes C62 . C63 . 1.383(6) yes C62 . H621 . 0.914 no C63 . C64 . 1.399(6) yes C63 . H631 . 0.937 no C64 . C65 . 1.372(6) yes C64 . H641 . 0.920 no C65 . C66 . 1.488(6) yes C66 . C67 . 1.383(6) yes C67 . C68 . 1.372(6) yes C67 . H671 . 0.922 no C68 . C69 . 1.374(6) yes C68 . H681 . 0.940 no C69 . C70 . 1.389(6) yes C69 . H691 . 0.914 no C70 . C71 . 1.495(6) yes C71 . H711 . 0.941 no C71 . H712 . 0.954 no C71 . H713 . 0.957 no N9 . O1 . 1.207(6) yes N9 . O2 . 1.208(6) yes N9 . C81 . 1.465(7) yes C81 . H811 . 0.964 no C81 . H812 . 0.968 no C81 . H813 . 0.966 no N10 . O3 . 1.229(6) yes N10 . O4 . 1.208(6) yes N10 . C82 . 1.426(8) yes C82 . H821 . 0.964 no C82 . H822 . 0.940 no C82 . H823 . 0.955 no P1 . F1 . 1.587(3) yes P1 . F2 . 1.582(3) yes P1 . F3 . 1.598(3) yes P1 . F4 . 1.589(3) yes P1 . F5 . 1.588(3) yes P1 . F6 . 1.593(3) yes P2 . F7 . 1.584(4) yes P2 . F8 . 1.577(4) yes P2 . F9 . 1.581(3) yes P2 . F10 . 1.586(3) yes P2 . F11 . 1.585(3) yes P2 . F12 . 1.534(3) yes 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 N1 . Cu1 . N2 . 81.81(14) yes N1 . Cu1 . N5 . 120.79(15) yes N2 . Cu1 . N5 . 135.88(14) yes N1 . Cu1 . N6 . 128.86(14) yes N2 . Cu1 . N6 . 115.71(15) yes N5 . Cu1 . N6 . 80.92(16) yes N3 . Cu2 . N4 . 82.05(14) yes N3 . Cu2 . N7 . 118.91(14) yes N4 . Cu2 . N7 . 125.18(13) yes N3 . Cu2 . N8 . 135.69(13) yes N4 . Cu2 . N8 . 119.91(14) yes N7 . Cu2 . N8 . 81.39(14) yes Cu1 . N1 . C1 . 126.9(3) yes Cu1 . N1 . C5 . 113.8(3) yes C1 . N1 . C5 . 118.7(4) yes Cu1 . N2 . C6 . 112.9(3) yes Cu1 . N2 . C10 . 127.5(3) yes C6 . N2 . C10 . 118.6(4) yes N1 . C1 . C2 . 122.6(4) yes N1 . C1 . S1 . 110.8(3) yes C2 . C1 . S1 . 126.6(4) yes C1 . C2 . C3 . 118.2(4) yes C1 . C2 . H21 . 119.8 no C3 . C2 . H21 . 122.1 no C2 . C3 . C4 . 120.2(4) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 120.0 no C3 . C4 . C5 . 119.0(5) yes C3 . C4 . H41 . 121.3 no C5 . C4 . H41 . 119.6 no C4 . C5 . N1 . 121.3(4) yes C4 . C5 . C6 . 123.7(4) yes N1 . C5 . C6 . 115.0(4) yes C5 . C6 . N2 . 115.0(4) yes C5 . C6 . C7 . 123.0(4) yes N2 . C6 . C7 . 122.0(4) yes C6 . C7 . C8 . 119.2(5) yes C6 . C7 . H71 . 120.6 no C8 . C7 . H71 . 120.2 no C7 . C8 . C9 . 119.1(5) yes C7 . C8 . H81 . 120.1 no C9 . C8 . H81 . 120.8 no C8 . C9 . C10 . 120.4(5) yes C8 . C9 . H91 . 120.9 no C10 . C9 . H91 . 118.7 no C9 . C10 . N2 . 120.7(4) yes C9 . C10 . C11 . 122.1(4) yes N2 . C10 . C11 . 117.2(4) yes C10 . C11 . H111 . 110.8 no C10 . C11 . H112 . 110.6 no H111 . C11 . H112 . 108.5 no C10 . C11 . H113 . 109.1 no H111 . C11 . H113 . 109.4 no H112 . C11 . H113 . 108.5 no C1 . S1 . S2 . 105.48(15) yes S1 . S2 . S3 . 105.79(7) yes S2 . S3 . C21 . 105.09(16) yes Cu2 . N3 . C21 . 126.6(3) yes Cu2 . N3 . C25 . 114.3(3) yes C21 . N3 . C25 . 118.7(4) yes Cu2 . N4 . C26 . 113.4(3) yes Cu2 . N4 . C30 . 127.9(3) yes C26 . N4 . C30 . 118.7(4) yes S3 . C21 . N3 . 110.6(3) yes S3 . C21 . C22 . 126.2(4) yes N3 . C21 . C22 . 123.2(4) yes C21 . C22 . C23 . 117.8(5) yes C21 . C22 . H221 . 121.3 no C23 . C22 . H221 . 121.0 no C22 . C23 . C24 . 120.1(5) yes C22 . C23 . H231 . 120.1 no C24 . C23 . H231 . 119.8 no C23 . C24 . C25 . 119.2(5) yes C23 . C24 . H241 . 121.8 no C25 . C24 . H241 . 119.0 no C24 . C25 . N3 . 121.1(4) yes C24 . C25 . C26 . 123.9(4) yes N3 . C25 . C26 . 115.0(4) yes C25 . C26 . N4 . 115.1(4) yes C25 . C26 . C27 . 122.7(4) yes N4 . C26 . C27 . 122.2(4) yes C26 . C27 . C28 . 118.5(5) yes C26 . C27 . H271 . 121.1 no C28 . C27 . H271 . 120.5 no C27 . C28 . C29 . 119.9(5) yes C27 . C28 . H281 . 120.1 no C29 . C28 . H281 . 119.9 no C28 . C29 . C30 . 118.9(5) yes C28 . C29 . H291 . 121.1 no C30 . C29 . H291 . 120.0 no C29 . C30 . N4 . 121.8(4) yes C29 . C30 . C31 . 121.1(5) yes N4 . C30 . C31 . 117.1(4) yes C30 . C31 . H311 . 112.1 no C30 . C31 . H312 . 108.9 no H311 . C31 . H312 . 108.4 no C30 . C31 . H313 . 110.6 no H311 . C31 . H313 . 109.5 no H312 . C31 . H313 . 107.1 no Cu1 . N5 . C41 . 124.8(3) yes Cu1 . N5 . C45 . 115.4(3) yes C41 . N5 . C45 . 118.7(4) yes Cu1 . N6 . C46 . 113.1(3) yes Cu1 . N6 . C50 . 126.5(3) yes C46 . N6 . C50 . 119.3(4) yes N5 . C41 . C42 . 122.9(4) yes N5 . C41 . S4 . 110.3(3) yes C42 . C41 . S4 . 126.7(4) yes C41 . C42 . C43 . 117.6(5) yes C41 . C42 . H421 . 121.1 no C43 . C42 . H421 . 121.2 no C42 . C43 . C44 . 120.0(5) yes C42 . C43 . H431 . 119.8 no C44 . C43 . H431 . 120.2 no C43 . C44 . C45 . 118.7(5) yes C43 . C44 . H441 . 120.7 no C45 . C44 . H441 . 120.6 no C44 . C45 . N5 . 122.1(5) yes C44 . C45 . C46 . 123.9(4) yes N5 . C45 . C46 . 113.9(4) yes C45 . C46 . N6 . 114.8(4) yes C45 . C46 . C47 . 123.8(5) yes N6 . C46 . C47 . 121.4(5) yes C46 . C47 . C48 . 119.1(5) yes C46 . C47 . H471 . 120.0 no C48 . C47 . H471 . 120.9 no C47 . C48 . C49 . 120.1(5) yes C47 . C48 . H481 . 119.5 no C49 . C48 . H481 . 120.4 no C48 . C49 . C50 . 119.1(5) yes C48 . C49 . H491 . 121.2 no C50 . C49 . H491 . 119.7 no C49 . C50 . N6 . 120.9(5) yes C49 . C50 . C51 . 121.9(5) yes N6 . C50 . C51 . 117.2(4) yes C50 . C51 . H511 . 109.1 no C50 . C51 . H512 . 109.7 no H511 . C51 . H512 . 109.7 no C50 . C51 . H513 . 110.4 no H511 . C51 . H513 . 109.8 no H512 . C51 . H513 . 108.1 no C41 . S4 . S5 . 104.54(19) yes S4 . S5 . S6 . 105.23(7) yes S5 . S6 . C61 . 104.64(17) yes Cu2 . N7 . C61 . 126.7(3) yes Cu2 . N7 . C65 . 114.2(3) yes C61 . N7 . C65 . 118.6(4) yes Cu2 . N8 . C66 . 114.4(3) yes Cu2 . N8 . C70 . 126.7(3) yes C66 . N8 . C70 . 118.5(3) yes S6 . C61 . N7 . 110.0(3) yes S6 . C61 . C62 . 126.1(4) yes N7 . C61 . C62 . 123.9(4) yes C61 . C62 . C63 . 117.6(4) yes C61 . C62 . H621 . 121.4 no C63 . C62 . H621 . 120.9 no C62 . C63 . C64 . 119.6(4) yes C62 . C63 . H631 . 120.7 no C64 . C63 . H631 . 119.8 no C63 . C64 . C65 . 118.7(4) yes C63 . C64 . H641 . 120.3 no C65 . C64 . H641 . 121.0 no C64 . C65 . N7 . 121.6(4) yes C64 . C65 . C66 . 123.5(4) yes N7 . C65 . C66 . 114.9(4) yes C65 . C66 . N8 . 114.6(4) yes C65 . C66 . C67 . 123.2(4) yes N8 . C66 . C67 . 122.3(4) yes C66 . C67 . C68 . 118.6(4) yes C66 . C67 . H671 . 121.8 no C68 . C67 . H671 . 119.6 no C67 . C68 . C69 . 119.9(4) yes C67 . C68 . H681 . 119.1 no C69 . C68 . H681 . 120.9 no C68 . C69 . C70 . 119.5(4) yes C68 . C69 . H691 . 120.7 no C70 . C69 . H691 . 119.8 no C69 . C70 . N8 . 121.1(4) yes C69 . C70 . C71 . 122.6(4) yes N8 . C70 . C71 . 116.2(4) yes C70 . C71 . H711 . 110.0 no C70 . C71 . H712 . 111.2 no H711 . C71 . H712 . 110.1 no C70 . C71 . H713 . 109.7 no H711 . C71 . H713 . 107.8 no H712 . C71 . H713 . 108.0 no O1 . N9 . O2 . 124.9(7) yes O1 . N9 . C81 . 117.5(6) yes O2 . N9 . C81 . 117.6(6) yes N9 . C81 . H811 . 108.6 no N9 . C81 . H812 . 108.7 no H811 . C81 . H812 . 110.8 no N9 . C81 . H813 . 108.8 no H811 . C81 . H813 . 108.7 no H812 . C81 . H813 . 111.2 no O3 . N10 . O4 . 124.8(7) yes O3 . N10 . C82 . 116.3(6) yes O4 . N10 . C82 . 118.9(7) yes N10 . C82 . H821 . 108.1 no N10 . C82 . H822 . 108.9 no H821 . C82 . H822 . 111.0 no N10 . C82 . H823 . 109.3 no H821 . C82 . H823 . 111.0 no H822 . C82 . H823 . 108.6 no F1 . P1 . F2 . 179.50(18) yes F1 . P1 . F3 . 89.08(17) yes F2 . P1 . F3 . 90.59(17) yes F1 . P1 . F4 . 90.65(19) yes F2 . P1 . F4 . 89.73(17) yes F3 . P1 . F4 . 90.11(16) yes F1 . P1 . F5 . 90.97(17) yes F2 . P1 . F5 . 89.36(18) yes F3 . P1 . F5 . 179.83(18) yes F4 . P1 . F5 . 90.05(17) yes F1 . P1 . F6 . 89.43(19) yes F2 . P1 . F6 . 90.19(17) yes F3 . P1 . F6 . 89.41(15) yes F4 . P1 . F6 . 179.52(18) yes F5 . P1 . F6 . 90.43(17) yes F7 . P2 . F8 . 176.0(2) yes F7 . P2 . F9 . 90.9(2) yes F8 . P2 . F9 . 89.1(2) yes F7 . P2 . F10 . 89.5(2) yes F8 . P2 . F10 . 86.5(2) yes F9 . P2 . F10 . 89.6(2) yes F7 . P2 . F11 . 88.81(18) yes F8 . P2 . F11 . 91.06(19) yes F9 . P2 . F11 . 178.9(2) yes F10 . P2 . F11 . 89.34(18) yes F7 . P2 . F12 . 89.2(3) yes F8 . P2 . F12 . 94.8(3) yes F9 . P2 . F12 . 90.8(2) yes F10 . P2 . F12 . 178.6(3) yes F11 . P2 . F12 . 90.3(2) yes # Attachment 'jp29.cif' data_jp29_8 _database_code_depnum_ccdc_archive 'CCDC 765879' #TrackingRef 'jp29.cif' _audit_creation_date 08-05-20 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'jp29_8_173k_0m in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.8298(3) _cell_length_b 9.2158(3) _cell_length_c 16.7316(6) _cell_angle_alpha 95.463(2) _cell_angle_beta 99.3650(10) _cell_angle_gamma 106.1230(10) _cell_volume 1276.29(8) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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' 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' 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' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 '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' 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' _cell_formula_units_Z 2 # Given Formula = C22 H18 Cl4 Cu1 N4 O1 S2 # Dc = 1.62 Fooo = 638.00 Mu = 14.62 M = 623.90 # Found Formula = C22 H22 Cl4 Cu1 N4 O1 S2 # Dc = 1.63 FOOO = 638.00 Mu = 14.63 M = 627.93 _chemical_formula_sum 'C22 H22 Cl4 Cu1 N4 O1 S2' _chemical_formula_moiety 'C22 H20 N4 S2, Cl4 Cu, H2 O ' _chemical_compound_source ? _chemical_formula_weight 627.93 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 1.463 # Sheldrick geometric approximatio 0.83 0.90 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.90 # 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_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _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 173 _diffrn_reflns_number 54610 _reflns_number_total 9225 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections with Friedels Law is 9225 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9295 _diffrn_reflns_theta_min 2.326 _diffrn_reflns_theta_max 32.574 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 31.271 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.44 _refine_diff_density_max 0.65 _refine_ls_number_reflns 7853 _refine_ls_number_restraints 0 _refine_ls_number_parameters 307 #_refine_ls_R_factor_ref 0.0212 _refine_ls_wR_factor_ref 0.0189 _refine_ls_goodness_of_fit_ref 1.0669 #_reflns_number_all 9212 _refine_ls_R_factor_all 0.0250 _refine_ls_wR_factor_all 0.0216 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 7853 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_gt 0.0189 _refine_ls_shift/su_max 0.002946 # 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 . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, 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: 0.153 -0.180 -0.643E-01 -0.137 ; _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_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 Fih. ; ? ; _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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). 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. 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 atomsattached 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 Cu1 Cu 0.107892(12) 0.847031(12) 0.765875(6) 0.0180 1.0000 Uani . . . . . . Cl1 Cl -0.00725(3) 0.71803(3) 0.857288(14) 0.0303 1.0000 Uani . . . . . . Cl2 Cl 0.35100(2) 0.97853(2) 0.841856(12) 0.0212 1.0000 Uani . . . . . . Cl3 Cl 0.04362(3) 0.66226(2) 0.657391(13) 0.0231 1.0000 Uani . . . . . . Cl4 Cl 0.03347(3) 1.03848(3) 0.707206(13) 0.0251 1.0000 Uani . . . . . . S1 S 0.63023(3) 0.53739(3) 0.723370(13) 0.0253 1.0000 Uani . . . . . . S2 S 0.54179(3) 0.68041(3) 0.788861(14) 0.0249 1.0000 Uani . . . . . . N1 N 0.62411(8) 0.17942(8) 0.48836(4) 0.0155 1.0000 Uani . . . . . . N2 N 0.52262(8) 0.36376(8) 0.58372(4) 0.0174 1.0000 Uani . . . . . . N3 N 0.39802(9) 0.64923(8) 0.91176(4) 0.0186 1.0000 Uani . . . . . . N4 N 0.27654(8) 0.81813(8) 1.00892(4) 0.0168 1.0000 Uani . . . . . . C1 C 0.85196(11) 0.07925(11) 0.48500(5) 0.0232 1.0000 Uani . . . . . . C2 C 0.69235(9) 0.09077(9) 0.44667(5) 0.0174 1.0000 Uani . . . . . . C3 C 0.61031(11) 0.01326(10) 0.36970(5) 0.0220 1.0000 Uani . . . . . . C4 C 0.46220(11) 0.02909(11) 0.33764(5) 0.0239 1.0000 Uani . . . . . . C5 C 0.39539(10) 0.12186(10) 0.38210(5) 0.0211 1.0000 Uani . . . . . . C6 C 0.47929(9) 0.19816(9) 0.45873(5) 0.0159 1.0000 Uani . . . . . . C7 C 0.42190(9) 0.29941(9) 0.51215(5) 0.0165 1.0000 Uani . . . . . . C8 C 0.27464(10) 0.32593(10) 0.48876(5) 0.0219 1.0000 Uani . . . . . . C9 C 0.22997(10) 0.42163(11) 0.54368(6) 0.0247 1.0000 Uani . . . . . . C10 C 0.33045(10) 0.48736(10) 0.61821(6) 0.0230 1.0000 Uani . . . . . . C11 C 0.47758(10) 0.45599(9) 0.63457(5) 0.0186 1.0000 Uani . . . . . . C12 C 0.42715(10) 0.56466(10) 0.85041(5) 0.0203 1.0000 Uani . . . . . . C13 C 0.37000(14) 0.40575(11) 0.83550(6) 0.0290 1.0000 Uani . . . . . . C14 C 0.27885(16) 0.33296(11) 0.88812(7) 0.0342 1.0000 Uani . . . . . . C15 C 0.24786(13) 0.41818(10) 0.95309(6) 0.0288 1.0000 Uani . . . . . . C16 C 0.30896(10) 0.57624(9) 0.96179(5) 0.0190 1.0000 Uani . . . . . . C17 C 0.27085(10) 0.67597(9) 1.02488(5) 0.0187 1.0000 Uani . . . . . . C18 C 0.22293(13) 0.63174(11) 1.09562(6) 0.0272 1.0000 Uani . . . . . . C19 C 0.17821(14) 0.73330(13) 1.14693(6) 0.0319 1.0000 Uani . . . . . . C20 C 0.18030(12) 0.87597(12) 1.12699(6) 0.0270 1.0000 Uani . . . . . . C21 C 0.23100(10) 0.91872(10) 1.05602(5) 0.0196 1.0000 Uani . . . . . . C22 C 0.23172(12) 1.06617(10) 1.02704(6) 0.0269 1.0000 Uani . . . . . . O1 O 0.85490(10) 0.29945(9) 0.64384(5) 0.0327 1.0000 Uani . . . . . . H1 H 0.6737 0.2302 0.5365 0.0205 1.0000 Uiso . . . . . . H2 H 0.3097 0.8424 0.9633 0.0212 1.0000 Uiso . . . . . . H3 H 0.8941 0.3953 0.6511 0.0492 1.0000 Uiso . . . . . . H4 H 0.9232 0.2611 0.6618 0.0495 1.0000 Uiso . . . . . . H11 H 0.8870 0.0165 0.4481 0.0395 1.0000 Uiso . . . . . . H12 H 0.8482 0.0344 0.5343 0.0387 1.0000 Uiso . . . . . . H13 H 0.9276 0.1752 0.4961 0.0392 1.0000 Uiso . . . . . . H31 H 0.6571 -0.0505 0.3401 0.0264 1.0000 Uiso . . . . . . H41 H 0.4077 -0.0223 0.2852 0.0287 1.0000 Uiso . . . . . . H51 H 0.2910 0.1343 0.3599 0.0242 1.0000 Uiso . . . . . . H81 H 0.2072 0.2814 0.4362 0.0271 1.0000 Uiso . . . . . . H91 H 0.1331 0.4445 0.5302 0.0310 1.0000 Uiso . . . . . . H101 H 0.3007 0.5545 0.6579 0.0292 1.0000 Uiso . . . . . . H131 H 0.3925 0.3469 0.7900 0.0348 1.0000 Uiso . . . . . . H141 H 0.2359 0.2220 0.8798 0.0416 1.0000 Uiso . . . . . . H151 H 0.1859 0.3713 0.9912 0.0355 1.0000 Uiso . . . . . . H181 H 0.2204 0.5336 1.1077 0.0338 1.0000 Uiso . . . . . . H191 H 0.1454 0.7023 1.1949 0.0392 1.0000 Uiso . . . . . . H201 H 0.1425 0.9468 1.1618 0.0321 1.0000 Uiso . . . . . . H221 H 0.1816 1.1226 1.0625 0.0410 1.0000 Uiso . . . . . . H222 H 0.1627 1.0466 0.9717 0.0413 1.0000 Uiso . . . . . . H223 H 0.3407 1.1261 1.0248 0.0424 1.0000 Uiso . . . . . . 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 Cu1 0.01929(4) 0.01992(4) 0.01481(4) 0.00243(3) 0.00188(3) 0.00677(3) Cl1 0.02345(9) 0.03961(12) 0.02080(9) 0.00871(8) 0.00248(7) -0.00220(8) Cl2 0.01964(8) 0.02259(8) 0.01974(8) 0.00143(6) 0.00241(6) 0.00484(6) Cl3 0.02411(9) 0.02360(9) 0.02117(8) -0.00166(7) 0.00155(7) 0.00970(7) Cl4 0.03072(10) 0.02777(9) 0.02248(9) 0.00600(7) 0.00521(7) 0.01701(8) S1 0.02194(9) 0.03619(11) 0.01804(8) -0.00510(8) 0.00246(7) 0.01274(8) S2 0.03096(10) 0.02280(9) 0.02147(9) -0.00136(7) 0.01208(8) 0.00644(8) N1 0.0153(3) 0.0174(3) 0.0142(2) 0.0018(2) 0.0032(2) 0.0054(2) N2 0.0166(3) 0.0211(3) 0.0159(3) 0.0011(2) 0.0030(2) 0.0083(2) N3 0.0218(3) 0.0183(3) 0.0170(3) 0.0020(2) 0.0054(2) 0.0074(2) N4 0.0187(3) 0.0184(3) 0.0132(3) 0.0010(2) 0.0043(2) 0.0052(2) C1 0.0209(3) 0.0308(4) 0.0225(4) 0.0044(3) 0.0068(3) 0.0136(3) C2 0.0190(3) 0.0188(3) 0.0168(3) 0.0036(2) 0.0070(2) 0.0073(2) C3 0.0246(4) 0.0244(4) 0.0176(3) -0.0002(3) 0.0075(3) 0.0075(3) C4 0.0247(4) 0.0280(4) 0.0159(3) -0.0016(3) 0.0028(3) 0.0053(3) C5 0.0189(3) 0.0267(4) 0.0157(3) 0.0013(3) 0.0011(2) 0.0056(3) C6 0.0154(3) 0.0175(3) 0.0150(3) 0.0026(2) 0.0033(2) 0.0049(2) C7 0.0151(3) 0.0186(3) 0.0169(3) 0.0030(2) 0.0033(2) 0.0063(2) C8 0.0167(3) 0.0266(4) 0.0229(4) 0.0019(3) 0.0009(3) 0.0096(3) C9 0.0174(3) 0.0289(4) 0.0300(4) 0.0026(3) 0.0030(3) 0.0121(3) C10 0.0197(3) 0.0265(4) 0.0261(4) 0.0009(3) 0.0065(3) 0.0121(3) C11 0.0176(3) 0.0224(3) 0.0175(3) 0.0018(3) 0.0047(2) 0.0082(3) C12 0.0241(4) 0.0200(3) 0.0182(3) 0.0008(3) 0.0049(3) 0.0091(3) C13 0.0412(5) 0.0203(4) 0.0280(4) -0.0002(3) 0.0107(4) 0.0124(4) C14 0.0514(6) 0.0175(4) 0.0366(5) 0.0047(3) 0.0161(5) 0.0105(4) C15 0.0392(5) 0.0184(4) 0.0319(5) 0.0076(3) 0.0137(4) 0.0085(3) C16 0.0221(3) 0.0185(3) 0.0184(3) 0.0040(3) 0.0047(3) 0.0083(3) C17 0.0203(3) 0.0205(3) 0.0162(3) 0.0041(2) 0.0045(2) 0.0063(3) C18 0.0343(4) 0.0298(4) 0.0208(4) 0.0103(3) 0.0109(3) 0.0095(3) C19 0.0381(5) 0.0407(5) 0.0200(4) 0.0079(4) 0.0149(4) 0.0102(4) C20 0.0282(4) 0.0350(5) 0.0181(3) -0.0012(3) 0.0094(3) 0.0089(3) C21 0.0191(3) 0.0226(3) 0.0157(3) -0.0024(3) 0.0035(2) 0.0057(3) C22 0.0348(5) 0.0212(4) 0.0255(4) -0.0022(3) 0.0086(3) 0.0101(3) O1 0.0324(4) 0.0275(3) 0.0368(4) -0.0003(3) -0.0016(3) 0.0131(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5247(2) 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 Cu1 . Cl1 . 2.2287(2) yes Cu1 . Cl2 . 2.2508(2) yes Cu1 . Cl3 . 2.2485(2) yes Cu1 . Cl4 . 2.2961(2) yes S1 . S2 . 2.0305(3) yes S1 . C11 . 1.7780(8) yes S2 . C12 . 1.7809(9) yes N1 . C2 . 1.3486(10) yes N1 . C6 . 1.3578(10) yes N1 . H1 . 0.872 no N2 . C7 . 1.3423(10) yes N2 . C11 . 1.3285(10) yes N3 . C12 . 1.3313(10) yes N3 . C16 . 1.3413(10) yes N4 . C17 . 1.3508(10) yes N4 . C21 . 1.3465(10) yes N4 . H2 . 0.887 no C1 . C2 . 1.4868(12) yes C1 . H11 . 0.952 no C1 . H12 . 0.959 no C1 . H13 . 0.929 no C2 . C3 . 1.3883(11) yes C3 . C4 . 1.3827(13) yes C3 . H31 . 0.952 no C4 . C5 . 1.3908(12) yes C4 . H41 . 0.940 no C5 . C6 . 1.3846(11) yes C5 . H51 . 0.978 no C6 . C7 . 1.4757(11) yes C7 . C8 . 1.3902(11) yes C8 . C9 . 1.3910(12) yes C8 . H81 . 0.960 no C9 . C10 . 1.3808(13) yes C9 . H91 . 0.934 no C10 . C11 . 1.3979(11) yes C10 . H101 . 0.981 no C12 . C13 . 1.3931(12) yes C13 . C14 . 1.3843(15) yes C13 . H131 . 0.971 no C14 . C15 . 1.3881(14) yes C14 . H141 . 0.974 no C15 . C16 . 1.3898(12) yes C15 . H151 . 0.963 no C16 . C17 . 1.4747(11) yes C17 . C18 . 1.3803(12) yes C18 . C19 . 1.3897(14) yes C18 . H181 . 0.941 no C19 . C20 . 1.3829(15) yes C19 . H191 . 0.940 no C20 . C21 . 1.3892(12) yes C20 . H201 . 0.994 no C21 . C22 . 1.4843(13) yes C22 . H221 . 0.986 no C22 . H222 . 0.993 no C22 . H223 . 0.976 no O1 . H3 . 0.843 no O1 . H4 . 0.812 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 Cl1 . Cu1 . Cl2 . 101.316(9) yes Cl1 . Cu1 . Cl3 . 101.039(10) yes Cl2 . Cu1 . Cl3 . 129.459(9) yes Cl1 . Cu1 . Cl4 . 126.118(10) yes Cl2 . Cu1 . Cl4 . 100.845(9) yes Cl3 . Cu1 . Cl4 . 101.409(9) yes S2 . S1 . C11 . 104.72(3) yes S1 . S2 . C12 . 105.16(3) yes C2 . N1 . C6 . 123.41(7) yes C2 . N1 . H1 . 120.5 no C6 . N1 . H1 . 116.1 no C7 . N2 . C11 . 117.90(7) yes C12 . N3 . C16 . 117.68(7) yes C17 . N4 . C21 . 124.06(7) yes C17 . N4 . H2 . 115.8 no C21 . N4 . H2 . 120.1 no C2 . C1 . H11 . 109.6 no C2 . C1 . H12 . 112.0 no H11 . C1 . H12 . 107.5 no C2 . C1 . H13 . 110.1 no H11 . C1 . H13 . 107.7 no H12 . C1 . H13 . 109.7 no C1 . C2 . N1 . 118.79(7) yes C1 . C2 . C3 . 122.57(7) yes N1 . C2 . C3 . 118.63(7) yes C2 . C3 . C4 . 119.60(8) yes C2 . C3 . H31 . 119.2 no C4 . C3 . H31 . 121.2 no C3 . C4 . C5 . 120.35(8) yes C3 . C4 . H41 . 119.4 no C5 . C4 . H41 . 120.3 no C4 . C5 . C6 . 119.10(8) yes C4 . C5 . H51 . 121.0 no C6 . C5 . H51 . 119.9 no C5 . C6 . N1 . 118.91(7) yes C5 . C6 . C7 . 124.52(7) yes N1 . C6 . C7 . 116.57(6) yes C6 . C7 . N2 . 115.05(7) yes C6 . C7 . C8 . 121.74(7) yes N2 . C7 . C8 . 123.21(7) yes C7 . C8 . C9 . 117.56(8) yes C7 . C8 . H81 . 121.2 no C9 . C8 . H81 . 121.2 no C8 . C9 . C10 . 120.30(8) yes C8 . C9 . H91 . 120.6 no C10 . C9 . H91 . 119.1 no C9 . C10 . C11 . 117.36(8) yes C9 . C10 . H101 . 121.5 no C11 . C10 . H101 . 121.1 no S1 . C11 . C10 . 125.01(6) yes S1 . C11 . N2 . 111.33(6) yes C10 . C11 . N2 . 123.64(8) yes S2 . C12 . N3 . 111.51(6) yes S2 . C12 . C13 . 124.82(7) yes N3 . C12 . C13 . 123.64(8) yes C12 . C13 . C14 . 117.62(8) yes C12 . C13 . H131 . 121.9 no C14 . C13 . H131 . 120.5 no C13 . C14 . C15 . 119.98(9) yes C13 . C14 . H141 . 120.4 no C15 . C14 . H141 . 119.6 no C14 . C15 . C16 . 117.71(9) yes C14 . C15 . H151 . 122.2 no C16 . C15 . H151 . 120.1 no C15 . C16 . N3 . 123.35(8) yes C15 . C16 . C17 . 121.32(8) yes N3 . C16 . C17 . 115.23(7) yes C16 . C17 . N4 . 116.33(7) yes C16 . C17 . C18 . 124.81(8) yes N4 . C17 . C18 . 118.78(8) yes C17 . C18 . C19 . 119.00(9) yes C17 . C18 . H181 . 119.4 no C19 . C18 . H181 . 121.6 no C18 . C19 . C20 . 120.47(8) yes C18 . C19 . H191 . 118.5 no C20 . C19 . H191 . 121.0 no C19 . C20 . C21 . 119.49(8) yes C19 . C20 . H201 . 120.8 no C21 . C20 . H201 . 119.6 no C20 . C21 . N4 . 118.12(8) yes C20 . C21 . C22 . 123.99(8) yes N4 . C21 . C22 . 117.84(7) yes C21 . C22 . H221 . 109.7 no C21 . C22 . H222 . 109.6 no H221 . C22 . H222 . 105.4 no C21 . C22 . H223 . 110.9 no H221 . C22 . H223 . 111.8 no H222 . C22 . H223 . 109.3 no H3 . O1 . H4 . 109.7 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 N1 . H1 . O1 . 157 0.87 2.11 2.936(2) yes # Attachment 'jp5.cif' data_jp5 _database_code_depnum_ccdc_archive 'CCDC 765880' #TrackingRef 'jp5.cif' _audit_creation_date 10-01-20 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title '4171010 jp5_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.7126(8) _cell_length_b 13.4955(10) _cell_length_c 7.1375(6) _cell_angle_alpha 90 _cell_angle_beta 107.011(3) _cell_angle_gamma 90 _cell_volume 986.74(13) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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' 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' 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 = C11 H10 N2 S1 # Dc = 1.36 Fooo = 424.00 Mu = 2.85 M = 202.28 # Found Formula = C11 H10 N2 S1 # Dc = 1.36 FOOO = 424.00 Mu = 2.85 M = 202.28 _chemical_formula_sum 'C11 H10 N2 S1' _chemical_formula_moiety 'C11 H10 N2 S1' _chemical_compound_source ? _chemical_formula_weight 202.28 _cell_measurement_reflns_used 4403 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.49 _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.285 # Sheldrick geometric approximatio 0.98 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _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 173 _diffrn_reflns_number 8599 _reflns_number_total 2288 _diffrn_reflns_av_R_equivalents 0.069 # Number of reflections with Friedels Law is 2288 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2253 _diffrn_reflns_theta_min 1.988 _diffrn_reflns_theta_max 27.634 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.634 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min 0 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min -9 _reflns_limit_l_max 8 _oxford_diffrn_Wilson_B_factor 3.19 _oxford_diffrn_Wilson_scale 2.60 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.99 _refine_diff_density_max 0.98 # 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 1247 _refine_ls_number_restraints 0 _refine_ls_number_parameters 128 _oxford_refine_ls_R_factor_ref 0.1071 _refine_ls_wR_factor_ref 0.0899 _refine_ls_goodness_of_fit_ref 0.8362 _refine_ls_shift/su_max 0.000031 # The values computed from all data _oxford_reflns_number_all 2275 _refine_ls_R_factor_all 0.1430 _refine_ls_wR_factor_all 0.0992 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1410 _refine_ls_R_factor_gt 0.1118 _refine_ls_wR_factor_gt 0.0915 # 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 . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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: 2.90 1.50 2.11 ; # 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. Nonius (1997-2001). 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. 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 atomsattached 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens S1 S -0.19584(14) 0.04958(10) 0.3413(2) 0.0487 1.0000 Uani . . . . . . . N1 N 0.0112(4) 0.1558(3) 0.3319(6) 0.0362 1.0000 Uani . . . . . . . N2 N 0.2486(4) 0.1226(3) 0.2942(6) 0.0364 1.0000 Uani . . . . . . . C1 C -0.1155(5) 0.1565(4) 0.3330(8) 0.0389 1.0000 Uani . . . . . . . C2 C -0.1701(5) 0.2533(4) 0.3299(8) 0.0412 1.0000 Uani . . . . . . . C3 C -0.0980(5) 0.3354(4) 0.3236(8) 0.0433 1.0000 Uani . . . . . . . C4 C 0.0318(5) 0.3289(4) 0.3195(7) 0.0391 1.0000 Uani . . . . . . . C5 C 0.0858(5) 0.2369(4) 0.3239(7) 0.0356 1.0000 Uani . . . . . . . C6 C 0.2208(5) 0.2176(4) 0.3213(7) 0.0343 1.0000 Uani . . . . . . . C7 C 0.3122(5) 0.2932(4) 0.3465(8) 0.0395 1.0000 Uani . . . . . . . C8 C 0.4385(5) 0.2689(4) 0.3548(8) 0.0430 1.0000 Uani . . . . . . . C9 C 0.4686(5) 0.1707(4) 0.3288(8) 0.0425 1.0000 Uani . . . . . . . C10 C 0.3700(5) 0.0996(4) 0.2955(8) 0.0375 1.0000 Uani . . . . . . . C11 C 0.3964(5) -0.0061(4) 0.2534(9) 0.0474 1.0000 Uani . . . . . . . H21 H -0.2557 0.2615 0.3322 0.0496 1.0000 Uiso R . . . . . . H31 H -0.1343 0.3987 0.3227 0.0526 1.0000 Uiso R . . . . . . H41 H 0.0789 0.3858 0.3125 0.0469 1.0000 Uiso R . . . . . . H71 H 0.2893 0.3585 0.3588 0.0482 1.0000 Uiso R . . . . . . H81 H 0.5030 0.3170 0.3790 0.0507 1.0000 Uiso R . . . . . . H91 H 0.5521 0.1522 0.3332 0.0519 1.0000 Uiso R . . . . . . H112 H 0.4885 -0.0140 0.2768 0.0700 1.0000 Uiso R . . . . . . H113 H 0.3672 -0.0484 0.3400 0.0697 1.0000 Uiso R . . . . . . H111 H 0.3519 -0.0221 0.1200 0.0697 1.0000 Uiso R . . . . . . H11 H 0.0491 0.0982 0.3372 0.0432 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 0.0421(7) 0.0373(7) 0.0695(11) -0.0082(8) 0.0206(7) -0.0042(7) N1 0.038(2) 0.034(2) 0.037(2) 0.0004(19) 0.0112(19) 0.0029(18) N2 0.043(2) 0.029(2) 0.037(2) 0.0045(19) 0.0108(19) -0.0006(18) C1 0.036(3) 0.031(2) 0.050(3) -0.003(2) 0.014(2) 0.000(2) C2 0.042(3) 0.038(3) 0.046(3) 0.003(2) 0.016(2) 0.002(2) C3 0.048(3) 0.039(3) 0.045(3) 0.004(3) 0.016(3) 0.011(2) C4 0.047(3) 0.037(3) 0.035(3) 0.007(2) 0.014(2) 0.005(2) C5 0.045(3) 0.032(2) 0.031(3) 0.001(2) 0.012(2) -0.001(2) C6 0.040(3) 0.032(2) 0.032(3) 0.006(2) 0.012(2) 0.003(2) C7 0.047(3) 0.032(2) 0.040(3) 0.005(2) 0.014(2) -0.001(2) C8 0.041(3) 0.035(3) 0.051(3) 0.004(2) 0.010(2) -0.008(2) C9 0.032(2) 0.046(3) 0.051(3) 0.004(3) 0.014(2) 0.003(2) C10 0.038(3) 0.037(3) 0.036(3) 0.004(2) 0.010(2) 0.003(2) C11 0.038(3) 0.041(3) 0.061(4) -0.006(3) 0.011(3) 0.002(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.693(6) loop_ _oxford_twin_element_scale_factors 0.763(11) 0.432(11) 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 . C1 . 1.690(5) yes N1 . C1 . 1.360(6) yes N1 . C5 . 1.367(6) yes N1 . H11 . 0.872 no N2 . C6 . 1.342(6) yes N2 . C10 . 1.334(7) yes C1 . C2 . 1.428(7) yes C2 . C3 . 1.358(8) yes C2 . H21 . 0.930 no C3 . C4 . 1.402(7) yes C3 . H31 . 0.938 no C4 . C5 . 1.365(7) yes C4 . H41 . 0.929 no C5 . C6 . 1.475(7) yes C6 . C7 . 1.389(7) yes C7 . C8 . 1.376(7) yes C7 . H71 . 0.927 no C8 . C9 . 1.389(7) yes C8 . H81 . 0.927 no C9 . C10 . 1.395(7) yes C9 . H91 . 0.921 no C10 . C11 . 1.501(7) yes C11 . H112 . 0.957 no C11 . H113 . 0.959 no C11 . H111 . 0.957 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 C1 . N1 . C5 . 126.2(4) yes C1 . N1 . H11 . 117.3 no C5 . N1 . H11 . 116.4 no C6 . N2 . C10 . 118.6(4) yes N1 . C1 . S1 . 120.9(4) yes N1 . C1 . C2 . 114.3(4) yes S1 . C1 . C2 . 124.8(4) yes C1 . C2 . C3 . 120.8(5) yes C1 . C2 . H21 . 120.7 no C3 . C2 . H21 . 118.5 no C2 . C3 . C4 . 121.8(5) yes C2 . C3 . H31 . 120.3 no C4 . C3 . H31 . 117.9 no C3 . C4 . C5 . 118.2(5) yes C3 . C4 . H41 . 120.5 no C5 . C4 . H41 . 121.3 no N1 . C5 . C4 . 118.7(4) yes N1 . C5 . C6 . 116.5(4) yes C4 . C5 . C6 . 124.8(4) yes C5 . C6 . N2 . 115.5(4) yes C5 . C6 . C7 . 121.7(5) yes N2 . C6 . C7 . 122.8(4) yes C6 . C7 . C8 . 118.5(5) yes C6 . C7 . H71 . 121.0 no C8 . C7 . H71 . 120.5 no C7 . C8 . C9 . 119.0(5) yes C7 . C8 . H81 . 120.8 no C9 . C8 . H81 . 120.2 no C8 . C9 . C10 . 119.1(5) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 119.9 no C9 . C10 . N2 . 121.9(5) yes C9 . C10 . C11 . 120.7(5) yes N2 . C10 . C11 . 117.4(4) yes C10 . C11 . H112 . 108.4 no C10 . C11 . H113 . 108.6 no H112 . C11 . H113 . 109.7 no C10 . C11 . H111 . 110.2 no H112 . C11 . H111 . 109.7 no H113 . C11 . H111 . 110.2 no # Attachment 'jp56.cif' data_jp56 _database_code_depnum_ccdc_archive 'CCDC 765881' #TrackingRef 'jp56.cif' _audit_creation_date 08-01-21 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'jp56_173k_0m in P4(2)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.7648(2) _cell_length_b 13.7648(2) _cell_length_c 23.6808(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4486.79(15) _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 42/n ' _symmetry_space_group_name_Hall '-P 4bc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -y,x+1/2,z+1/2 y,-x+1/2,-z+1/2 -x+1/2,-y+1/2,z x+1/2,y+1/2,-z y+1/2,-x,z+1/2 -y+1/2,x,-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' 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' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 '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 = C44 H40 Cu1 F6 N8 P1 S4 # Dc = 1.62 Fooo = 2088.00 Mu = 11.79 M = 545.99 # Found Formula = C44 H40 Cu1 F6 N8 P1 S4 # Dc = 1.51 FOOO = 2088.00 Mu = 7.77 M = 508.81 _chemical_formula_sum 'C44 H40 Cu1 F6 N8 P1 S4' _chemical_formula_moiety 'C44 H40 Cu N8 S4, F6 P' _chemical_compound_source ? _chemical_formula_weight 1017.63 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 0.777 # Sheldrick geometric approximatio 0.91 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 # 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_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _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 173 _diffrn_reflns_number 80271 _reflns_number_total 10647 _diffrn_reflns_av_R_equivalents 0.060 # Number of reflections with Friedels Law is 10647 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 11292 _diffrn_reflns_theta_min 3.082 _diffrn_reflns_theta_max 36.851 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 33.903 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _reflns_limit_h_min -15 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 38 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.38 _refine_ls_number_reflns 5582 _refine_ls_number_restraints 0 _refine_ls_number_parameters 291 #_refine_ls_R_factor_ref 0.0262 _refine_ls_wR_factor_ref 0.0304 _refine_ls_goodness_of_fit_ref 1.0384 #_reflns_number_all 10640 _refine_ls_R_factor_all 0.0583 _refine_ls_wR_factor_all 0.0601 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 5582 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_gt 0.0304 _refine_ls_shift/su_max 0.003123 # 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 . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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: 0.485 0.486 0.268 ; _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_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 Fih. ; ? ; _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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). 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. 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 atomsattached 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 Cu1 Cu 0.2500 0.2500 0.504043(7) 0.0234 1.0000 Uani S T . . . . S1 S 0.17705(2) 0.15197(2) 0.436523(11) 0.0294 1.0000 Uani . . . . . . S2 S 0.33916(2) 0.17144(2) 0.574028(11) 0.0285 1.0000 Uani . . . . . . N1 N 0.13292(6) 0.03706(6) 0.52324(4) 0.0234 1.0000 Uani . . . . . . N2 N 0.10564(7) 0.05527(7) 0.63220(4) 0.0278 1.0000 Uani . . . . . . N3 N 0.46963(6) 0.13920(6) 0.49334(4) 0.0223 1.0000 Uani . . . . . . N4 N 0.47307(7) 0.13742(7) 0.38330(4) 0.0280 1.0000 Uani . . . . . . C1 C 0.14405(7) 0.04513(7) 0.46632(4) 0.0237 1.0000 Uani . . . . . . C2 C 0.12638(8) -0.04053(8) 0.43479(5) 0.0291 1.0000 Uani . . . . . . C3 C 0.09963(9) -0.12467(9) 0.46122(6) 0.0354 1.0000 Uani . . . . . . C4 C 0.08887(9) -0.12806(8) 0.52007(6) 0.0340 1.0000 Uani . . . . . . C5 C 0.10546(7) -0.04541(7) 0.55103(5) 0.0252 1.0000 Uani . . . . . . C6 C 0.09721(8) -0.03599(8) 0.61287(5) 0.0270 1.0000 Uani . . . . . . C7 C 0.08377(10) -0.11586(10) 0.64805(6) 0.0386 1.0000 Uani . . . . . . C8 C 0.08068(11) -0.09997(11) 0.70554(7) 0.0442 1.0000 Uani . . . . . . C9 C 0.08952(10) -0.00661(12) 0.72584(6) 0.0404 1.0000 Uani . . . . . . C10 C 0.10106(9) 0.07044(10) 0.68798(5) 0.0326 1.0000 Uani . . . . . . C11 C 0.10736(13) 0.17369(11) 0.70749(6) 0.0448 1.0000 Uani . . . . . . C12 C 0.45017(7) 0.13938(7) 0.54949(4) 0.0227 1.0000 Uani . . . . . . C13 C 0.52744(8) 0.11044(8) 0.58521(5) 0.0283 1.0000 Uani . . . . . . C14 C 0.61486(8) 0.08261(9) 0.56288(5) 0.0321 1.0000 Uani . . . . . . C15 C 0.62982(8) 0.08251(9) 0.50435(5) 0.0309 1.0000 Uani . . . . . . C16 C 0.55544(7) 0.11131(7) 0.46957(5) 0.0232 1.0000 Uani . . . . . . C17 C 0.55812(8) 0.11520(8) 0.40751(5) 0.0255 1.0000 Uani . . . . . . C18 C 0.64204(9) 0.09678(10) 0.37674(6) 0.0377 1.0000 Uani . . . . . . C19 C 0.63700(11) 0.10326(12) 0.31846(6) 0.0438 1.0000 Uani . . . . . . C20 C 0.54986(11) 0.12615(10) 0.29337(6) 0.0395 1.0000 Uani . . . . . . C21 C 0.46849(10) 0.14244(10) 0.32704(5) 0.0345 1.0000 Uani . . . . . . C22 C 0.37105(14) 0.16562(17) 0.30264(7) 0.0597 1.0000 Uani . . . . . . P1 P 0.2500 0.7500 0.322107(17) 0.0286 1.0000 Uani S T . . . . F1 F 0.2500 0.7500 0.38948(5) 0.0392 1.0000 Uani S T . . . . F2 F 0.2500 0.7500 0.25477(5) 0.0435 1.0000 Uani S T . . . . F3 F 0.26530(9) 0.86520(7) 0.32207(4) 0.0565 1.0000 Uani . . . . . . F5 F 0.13557(7) 0.76545(10) 0.32219(4) 0.0624 1.0000 Uani . . . . . . H21 H 0.1332 -0.0394 0.3950 0.0342 1.0000 Uiso R . . . . . H131 H 0.5170 0.1114 0.6244 0.0341 1.0000 Uiso R . . . . . H141 H 0.6639 0.0635 0.5871 0.0407 1.0000 Uiso R . . . . . H3 H 0.4253 0.1568 0.4701 0.0285 1.0000 Uiso R . . . . . H151 H 0.6890 0.0637 0.4891 0.0382 1.0000 Uiso R . . . . . H1 H 0.1423 0.0854 0.5440 0.0275 1.0000 Uiso R . . . . . H31 H 0.0887 -0.1809 0.4394 0.0426 1.0000 Uiso R . . . . . H41 H 0.0683 -0.1839 0.5376 0.0422 1.0000 Uiso R . . . . . H181 H 0.7000 0.0816 0.3940 0.0484 1.0000 Uiso R . . . . . H191 H 0.6925 0.0924 0.2966 0.0529 1.0000 Uiso R . . . . . H71 H 0.0778 -0.1789 0.6331 0.0483 1.0000 Uiso R . . . . . H81 H 0.0735 -0.1512 0.7313 0.0539 1.0000 Uiso R . . . . . H201 H 0.5454 0.1334 0.2544 0.0496 1.0000 Uiso R . . . . . H91 H 0.0880 0.0059 0.7642 0.0487 1.0000 Uiso R . . . . . H112 H 0.1172 0.1776 0.7471 0.0669 1.0000 Uiso R . . . . . H223 H 0.3745 0.1677 0.2627 0.0906 1.0000 Uiso R . . . . . H111 H 0.1586 0.2082 0.6901 0.0666 1.0000 Uiso R . . . . . H113 H 0.0493 0.2084 0.6986 0.0678 1.0000 Uiso R . . . . . H221 H 0.3519 0.2278 0.3154 0.0919 1.0000 Uiso R . . . . . H222 H 0.3241 0.1197 0.3134 0.0915 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 Cu1 0.02257(8) 0.02166(8) 0.02594(8) 0.0000 0.0000 0.00036(7) S1 0.03658(14) 0.02827(12) 0.02349(11) -0.00100(9) -0.00062(10) -0.00709(10) S2 0.02693(12) 0.03455(14) 0.02416(10) 0.00278(9) 0.00072(9) 0.00678(10) N1 0.0225(4) 0.0191(3) 0.0285(4) -0.0021(3) 0.0007(3) -0.0006(3) N2 0.0253(4) 0.0281(4) 0.0298(4) 0.0029(3) 0.0001(3) -0.0011(3) N3 0.0196(3) 0.0222(4) 0.0252(4) 0.0017(3) -0.0025(3) 0.0013(3) N4 0.0272(4) 0.0298(4) 0.0269(4) 0.0033(3) 0.0004(3) 0.0030(3) C1 0.0193(4) 0.0237(4) 0.0281(4) -0.0043(3) -0.0002(3) 0.0000(3) C2 0.0234(4) 0.0284(5) 0.0355(5) -0.0113(4) 0.0006(4) -0.0005(4) C3 0.0294(5) 0.0248(5) 0.0519(7) -0.0136(5) 0.0023(5) -0.0034(4) C4 0.0301(5) 0.0206(5) 0.0513(7) -0.0023(4) 0.0042(5) -0.0030(4) C5 0.0185(4) 0.0212(4) 0.0360(5) 0.0010(4) 0.0020(3) -0.0005(3) C6 0.0198(4) 0.0259(5) 0.0352(5) 0.0050(4) 0.0012(4) 0.0004(3) C7 0.0395(6) 0.0298(6) 0.0464(7) 0.0120(5) 0.0056(5) 0.0006(5) C8 0.0436(7) 0.0437(7) 0.0453(7) 0.0195(6) 0.0048(6) 0.0016(6) C9 0.0365(6) 0.0531(8) 0.0317(6) 0.0115(5) 0.0014(5) 0.0018(6) C10 0.0279(5) 0.0400(6) 0.0298(5) 0.0036(4) -0.0017(4) -0.0004(4) C11 0.0569(9) 0.0449(7) 0.0326(6) -0.0027(5) -0.0010(6) -0.0031(7) C12 0.0232(4) 0.0195(4) 0.0254(4) 0.0012(3) -0.0034(3) -0.0009(3) C13 0.0283(5) 0.0290(5) 0.0277(5) 0.0012(4) -0.0082(4) -0.0005(4) C14 0.0254(5) 0.0322(5) 0.0386(6) 0.0018(4) -0.0117(4) 0.0014(4) C15 0.0202(4) 0.0319(5) 0.0407(6) 0.0004(4) -0.0042(4) 0.0032(4) C16 0.0196(4) 0.0202(4) 0.0299(5) 0.0012(3) -0.0006(3) -0.0005(3) C17 0.0247(4) 0.0218(4) 0.0300(5) 0.0021(3) 0.0032(4) 0.0004(3) C18 0.0264(5) 0.0439(7) 0.0429(7) 0.0025(5) 0.0086(5) 0.0040(5) C19 0.0419(7) 0.0469(8) 0.0426(7) 0.0002(6) 0.0184(6) 0.0019(6) C20 0.0523(8) 0.0361(6) 0.0300(5) 0.0006(5) 0.0105(5) -0.0031(5) C21 0.0401(6) 0.0361(6) 0.0271(5) 0.0036(4) 0.0011(4) 0.0015(5) C22 0.0527(9) 0.0926(14) 0.0336(7) 0.0123(8) -0.0088(6) 0.0135(9) P1 0.02903(19) 0.0351(2) 0.02171(16) 0.0000 0.0000 0.00073(17) F1 0.0502(6) 0.0450(6) 0.0223(4) 0.0000 0.0000 0.0021(5) F2 0.0569(7) 0.0522(7) 0.0214(5) 0.0000 0.0000 -0.0017(6) F3 0.0957(8) 0.0378(5) 0.0360(4) 0.0007(3) 0.0032(5) -0.0090(5) F5 0.0318(4) 0.1057(9) 0.0498(6) 0.0059(5) -0.0012(4) 0.0106(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.19211(17) 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 Cu1 . S2 5_555 2.3286(3) yes Cu1 . S1 5_555 2.3207(3) yes Cu1 . S1 . 2.3207(3) yes Cu1 . S2 . 2.3286(3) yes S1 . C1 . 1.6932(11) yes S2 . C12 . 1.6933(11) yes N1 . C1 . 1.3612(14) yes N1 . C5 . 1.3656(13) yes N1 . H1 . 0.837 no N2 . C6 . 1.3420(15) yes N2 . C10 . 1.3388(15) yes N3 . C12 . 1.3564(13) yes N3 . C16 . 1.3636(13) yes N3 . H3 . 0.856 no N4 . C17 . 1.3388(14) yes N4 . C21 . 1.3356(15) yes C1 . C2 . 1.4165(14) yes C2 . C3 . 1.3670(18) yes C2 . H21 . 0.947 no C3 . C4 . 1.402(2) yes C3 . H31 . 0.943 no C4 . C5 . 1.3726(16) yes C4 . H41 . 0.918 no C5 . C6 . 1.4744(17) yes C6 . C7 . 1.3918(16) yes C7 . C8 . 1.379(2) yes C7 . H71 . 0.941 no C8 . C9 . 1.377(2) yes C8 . H81 . 0.937 no C9 . C10 . 1.3979(18) yes C9 . H91 . 0.924 no C10 . C11 . 1.497(2) yes C11 . H112 . 0.950 no C11 . H111 . 0.945 no C11 . H113 . 0.955 no C12 . C13 . 1.4161(14) yes C13 . C14 . 1.3690(17) yes C13 . H131 . 0.938 no C14 . C15 . 1.4014(18) yes C14 . H141 . 0.925 no C15 . C16 . 1.3725(15) yes C15 . H151 . 0.928 no C16 . C17 . 1.4712(16) yes C17 . C18 . 1.3892(16) yes C18 . C19 . 1.385(2) yes C18 . H181 . 0.920 no C19 . C20 . 1.375(2) yes C19 . H191 . 0.935 no C20 . C21 . 1.3930(19) yes C20 . H201 . 0.930 no C21 . C22 . 1.495(2) yes C22 . H223 . 0.948 no C22 . H221 . 0.945 no C22 . H222 . 0.939 no P1 . F3 5_565 1.5996(9) yes P1 . F5 5_565 1.5893(9) yes P1 . F1 . 1.5954(12) yes P1 . F2 . 1.5947(12) yes P1 . F3 . 1.5996(9) yes P1 . F5 . 1.5893(9) yes 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 S2 5_555 Cu1 . S1 5_555 116.641(10) yes S2 5_555 Cu1 . S1 . 122.163(10) yes S1 5_555 Cu1 . S1 . 92.900(15) yes S2 5_555 Cu1 . S2 . 89.250(15) yes S1 5_555 Cu1 . S2 . 122.163(10) yes S1 . Cu1 . S2 . 116.641(10) yes Cu1 . S1 . C1 . 109.51(4) yes Cu1 . S2 . C12 . 110.63(4) yes C1 . N1 . C5 . 125.19(9) yes C1 . N1 . H1 . 119.9 no C5 . N1 . H1 . 114.9 no C6 . N2 . C10 . 118.58(10) yes C12 . N3 . C16 . 125.18(9) yes C12 . N3 . H3 . 119.3 no C16 . N3 . H3 . 115.5 no C17 . N4 . C21 . 118.70(11) yes N1 . C1 . S1 . 120.91(7) yes N1 . C1 . C2 . 115.76(10) yes S1 . C1 . C2 . 123.33(9) yes C1 . C2 . C3 . 120.68(11) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 119.7 no C2 . C3 . C4 . 120.77(11) yes C2 . C3 . H31 . 119.1 no C4 . C3 . H31 . 120.1 no C3 . C4 . C5 . 119.06(11) yes C3 . C4 . H41 . 120.7 no C5 . C4 . H41 . 120.2 no C4 . C5 . N1 . 118.53(11) yes C4 . C5 . C6 . 126.20(11) yes N1 . C5 . C6 . 115.27(9) yes C5 . C6 . N2 . 114.48(10) yes C5 . C6 . C7 . 122.36(11) yes N2 . C6 . C7 . 123.15(12) yes C6 . C7 . C8 . 118.01(13) yes C6 . C7 . H71 . 121.0 no C8 . C7 . H71 . 121.0 no C7 . C8 . C9 . 119.31(12) yes C7 . C8 . H81 . 121.7 no C9 . C8 . H81 . 119.0 no C8 . C9 . C10 . 119.61(13) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 119.4 no C9 . C10 . N2 . 121.32(13) yes C9 . C10 . C11 . 121.93(12) yes N2 . C10 . C11 . 116.74(11) yes C10 . C11 . H112 . 111.6 no C10 . C11 . H111 . 112.7 no H112 . C11 . H111 . 107.2 no C10 . C11 . H113 . 111.0 no H112 . C11 . H113 . 108.0 no H111 . C11 . H113 . 106.1 no N3 . C12 . S2 . 121.01(7) yes N3 . C12 . C13 . 115.90(9) yes S2 . C12 . C13 . 123.10(8) yes C12 . C13 . C14 . 120.55(11) yes C12 . C13 . H131 . 118.1 no C14 . C13 . H131 . 121.3 no C13 . C14 . C15 . 120.76(10) yes C13 . C14 . H141 . 118.8 no C15 . C14 . H141 . 120.5 no C14 . C15 . C16 . 118.92(11) yes C14 . C15 . H151 . 121.0 no C16 . C15 . H151 . 120.1 no C15 . C16 . N3 . 118.68(10) yes C15 . C16 . C17 . 126.25(10) yes N3 . C16 . C17 . 115.07(9) yes C16 . C17 . N4 . 114.47(9) yes C16 . C17 . C18 . 122.56(11) yes N4 . C17 . C18 . 122.97(11) yes C17 . C18 . C19 . 117.99(13) yes C17 . C18 . H181 . 121.9 no C19 . C18 . H181 . 120.1 no C18 . C19 . C20 . 119.29(12) yes C18 . C19 . H191 . 120.0 no C20 . C19 . H191 . 120.7 no C19 . C20 . C21 . 119.40(13) yes C19 . C20 . H201 . 120.7 no C21 . C20 . H201 . 119.8 no C20 . C21 . N4 . 121.64(13) yes C20 . C21 . C22 . 122.32(12) yes N4 . C21 . C22 . 116.04(12) yes C21 . C22 . H223 . 110.4 no C21 . C22 . H221 . 108.7 no H223 . C22 . H221 . 107.7 no C21 . C22 . H222 . 111.7 no H223 . C22 . H222 . 109.0 no H221 . C22 . H222 . 109.3 no F3 5_565 P1 . F5 5_565 89.88(6) yes F3 5_565 P1 . F1 . 90.04(4) yes F5 5_565 P1 . F1 . 89.93(4) yes F3 5_565 P1 . F2 . 89.96(4) yes F5 5_565 P1 . F2 . 90.07(4) yes F1 . P1 . F2 . 179.993 yes F3 5_565 P1 . F3 . 179.93(7) yes F5 5_565 P1 . F3 . 90.12(6) yes F1 . P1 . F3 . 90.04(4) yes F2 . P1 . F3 . 89.96(4) yes F3 5_565 P1 . F5 . 90.12(6) yes F5 5_565 P1 . F5 . 179.86(8) yes F1 . P1 . F5 . 89.93(4) yes F2 . P1 . F5 . 90.07(4) yes F3 . P1 . F5 . 89.88(6) yes