# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 #TrackingRef '- 3_7a.cif' #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Josefina D\'iez Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; _publ_contact_author_phone '0034 98 5102960' _publ_contact_author_fax '0034 98 5103446' _publ_contact_author_email jdv@uniovi.es _publ_requested_coeditor_name ? _publ_contact_letter ; Oviedo 20/07/2010 Please receive the CIF for compounds 3 and 7a submitted to be published in Green Chemistry. Thank you very much. J. D\'iez. ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE, ABSTRACT AND AUTHOR LIST _publ_section_title ; Highly Efficient Copper(I) Catalyst for 1,3-Dipolar Cycloaddition of Azides with Terminal and 1-Iodoalkynes in Water: Regioselective Synthesis of 1,4-Disubstituted and 1,4,5-Trisubstituted-1,2,3-Triazoles. ; _publ_section_abstract ; A new water soluble Cu(I) complex which exhibits a versatile and highly catalytic activity for the Huisgen cycloadditions of azides and terminal alkynes in aqueous media under mild conditions is the first well-defined Cu(I) catalyst being active with 1-iodoalkynes in water and under aerobic conditions. ; # The loop structure below should contain the names and addresses of all #authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address J.Garcia-Alvarez ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; J.Diez ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; "Jos\'e Gimeno" ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; _publ_contact_author_name 'Josefina Diez' #=============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 785087' #TrackingRef '- 3_7a.cif' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H44 Cu N8 O4 P4 S2, F6 P' _chemical_formula_sum 'C20 H44 Cu F6 N8 O4 P5 S2' _chemical_formula_weight 857.14 _chemical_compound_source synthesis 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' O O 0.0106 0.0060 '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 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' _cell_length_a 10.4612(2) _cell_length_b 11.6733(2) _cell_length_c 15.4745(2) _cell_angle_alpha 80.696(1) _cell_angle_beta 70.225(1) _cell_angle_gamma 83.182(1) _cell_volume 1750.69(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5721 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 25.350 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22308 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.39 _reflns_number_total 6394 _reflns_number_gt 5322 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker, 2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowki & Minor 1997)' _computing_data_reduction 'HKL Denzo and scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0803P)^2^+0.4186P] 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 6394 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 C1 C 0.7429(4) 0.5555(3) 0.0654(2) 0.0148(7) Uani 1 1 d . . . H1A H 0.6871 0.4910 0.0973 0.018 Uiso 1 1 calc R . . H1B H 0.8374 0.5282 0.0554 0.018 Uiso 1 1 calc R . . C2 C 0.8147(4) 0.7330(3) -0.0847(2) 0.0163(7) Uani 1 1 d . . . H2A H 0.9112 0.7112 -0.0983 0.020 Uiso 1 1 calc R . . H2B H 0.8002 0.7745 -0.1406 0.020 Uiso 1 1 calc R . . C3 C 0.5449(4) 0.6673(3) -0.0098(3) 0.0195(8) Uani 1 1 d . . . H3A H 0.5226 0.7074 -0.0634 0.023 Uiso 1 1 calc R . . H3B H 0.4821 0.6068 0.0197 0.023 Uiso 1 1 calc R . . C4 C 0.5612(4) 0.6939(3) 0.1394(2) 0.0174(8) Uani 1 1 d . . . H4A H 0.5052 0.6282 0.1656 0.021 Uiso 1 1 calc R . . H4B H 0.5350 0.7484 0.1845 0.021 Uiso 1 1 calc R . . C5 C 0.6221(4) 0.8453(3) 0.0120(2) 0.0193(8) Uani 1 1 d . . . H5A H 0.6001 0.9047 0.0530 0.023 Uiso 1 1 calc R . . H5B H 0.6051 0.8801 -0.0447 0.023 Uiso 1 1 calc R . . C6 C 0.7930(4) 0.7511(3) 0.0746(2) 0.0156(7) Uani 1 1 d . . . H6A H 0.7779 0.8086 0.1164 0.019 Uiso 1 1 calc R . . H6B H 0.8879 0.7226 0.0588 0.019 Uiso 1 1 calc R . . C7 C 0.8022(4) 0.2222(3) -0.0709(3) 0.0225(8) Uani 1 1 d . . . H7A H 0.7374 0.2392 -0.1045 0.027 Uiso 1 1 calc R . . H7B H 0.7523 0.2184 -0.0052 0.027 Uiso 1 1 calc R . . C8 C 0.8808(4) 0.1089(4) -0.0918(3) 0.0313(10) Uani 1 1 d . . . H8A H 0.8212 0.0466 -0.0660 0.047 Uiso 1 1 calc R . . H8B H 0.9526 0.0977 -0.0650 0.047 Uiso 1 1 calc R . . H8C H 0.9192 0.1094 -0.1576 0.047 Uiso 1 1 calc R . . C9 C 0.7956(4) 0.4596(3) -0.3075(2) 0.0211(8) Uani 1 1 d . . . H9A H 0.8578 0.5194 -0.3408 0.025 Uiso 1 1 calc R . . H9B H 0.7080 0.4970 -0.2757 0.025 Uiso 1 1 calc R . . C10 C 0.7808(5) 0.3851(4) -0.3732(3) 0.0318(10) Uani 1 1 d . . . H10A H 0.7345 0.4302 -0.4127 0.048 Uiso 1 1 calc R . . H10B H 0.7292 0.3202 -0.3389 0.048 Uiso 1 1 calc R . . H10C H 0.8694 0.3573 -0.4103 0.048 Uiso 1 1 calc R . . C11 C 0.5883(4) 0.6915(3) 0.4172(2) 0.0159(7) Uani 1 1 d . . . H11A H 0.5643 0.6130 0.4450 0.019 Uiso 1 1 calc R . . H11B H 0.5255 0.7239 0.3842 0.019 Uiso 1 1 calc R . . C12 C 0.6422(4) 0.9121(3) 0.4387(2) 0.0177(8) Uani 1 1 d . . . H12A H 0.5815 0.9505 0.4057 0.021 Uiso 1 1 calc R . . H12B H 0.6512 0.9647 0.4785 0.021 Uiso 1 1 calc R . . C13 C 0.7124(4) 0.7139(3) 0.5480(2) 0.0202(8) Uani 1 1 d . . . H13A H 0.7242 0.7599 0.5913 0.024 Uiso 1 1 calc R . . H13B H 0.6923 0.6361 0.5796 0.024 Uiso 1 1 calc R . . C14 C 0.7683(4) 0.8082(3) 0.3072(2) 0.0166(7) Uani 1 1 d . . . H14A H 0.8556 0.8033 0.2585 0.020 Uiso 1 1 calc R . . H14B H 0.7014 0.8441 0.2787 0.020 Uiso 1 1 calc R . . C15 C 0.8732(4) 0.8264(3) 0.4188(3) 0.0220(8) Uani 1 1 d . . . H15A H 0.8761 0.8748 0.4634 0.026 Uiso 1 1 calc R . . H15B H 0.9635 0.8210 0.3735 0.026 Uiso 1 1 calc R . . C16 C 0.8271(4) 0.6381(3) 0.4007(2) 0.0184(8) Uani 1 1 d . . . H16A H 0.7989 0.5624 0.4333 0.022 Uiso 1 1 calc R . . H16B H 0.9166 0.6264 0.3555 0.022 Uiso 1 1 calc R . . C17 C 0.7188(5) 0.1805(4) 0.2166(3) 0.0330(10) Uani 1 1 d . . . H17A H 0.6851 0.2368 0.1745 0.040 Uiso 1 1 calc R . . H17B H 0.6440 0.1355 0.2571 0.040 Uiso 1 1 calc R . . C18 C 0.8305(5) 0.1022(4) 0.1632(3) 0.0364(11) Uani 1 1 d . . . H18A H 0.8676 0.0506 0.2050 0.055 Uiso 1 1 calc R . . H18B H 0.9008 0.1481 0.1197 0.055 Uiso 1 1 calc R . . H18C H 0.7952 0.0576 0.1305 0.055 Uiso 1 1 calc R . . C19 C 0.9237(9) 0.2539(6) 0.3962(4) 0.081(3) Uani 1 1 d . . . H19A H 0.9783 0.2472 0.3323 0.097 Uiso 1 1 calc R . . H19B H 0.9748 0.2900 0.4251 0.097 Uiso 1 1 calc R . . C20 C 0.8841(9) 0.1523(8) 0.4423(4) 0.108(4) Uani 1 1 d . . . H20A H 0.9624 0.0996 0.4406 0.162 Uiso 1 1 calc R . . H20B H 0.8284 0.1216 0.4145 0.162 Uiso 1 1 calc R . . H20C H 0.8324 0.1616 0.5055 0.162 Uiso 1 1 calc R . . N1 N 0.7063(3) 0.6518(2) 0.12417(18) 0.0132(6) Uani 1 1 d . . . N2 N 0.7672(3) 0.8078(3) -0.00973(19) 0.0162(6) Uani 1 1 d . . . N3 N 0.5319(3) 0.7505(3) 0.0560(2) 0.0173(7) Uani 1 1 d . . . N4 N 0.7356(3) 0.5031(3) -0.1081(2) 0.0160(6) Uani 1 1 d . . . N5 N 0.7304(3) 0.6879(3) 0.35058(19) 0.0147(6) Uani 1 1 d . . . N6 N 0.7774(3) 0.8831(3) 0.37172(19) 0.0180(7) Uani 1 1 d . . . N7 N 0.8386(3) 0.7089(3) 0.4672(2) 0.0198(7) Uani 1 1 d . . . N8 N 0.5744(3) 0.2027(3) 0.4209(2) 0.0220(7) Uani 1 1 d . . . O1 O 0.8989(3) 0.3136(2) -0.09934(17) 0.0187(5) Uani 1 1 d . . . O2 O 0.8485(3) 0.3836(2) -0.24144(16) 0.0169(5) Uani 1 1 d . . . O3 O 0.7731(3) 0.2399(2) 0.27080(16) 0.0205(6) Uani 1 1 d . . . O4 O 0.7782(3) 0.3251(2) 0.40352(18) 0.0257(6) Uani 1 1 d . . . F1 F 0.3909(4) 0.0456(3) 0.3514(2) 0.0732(12) Uani 1 1 d . . . F2 F 0.2089(5) 0.0140(7) 0.3169(5) 0.184(3) Uani 1 1 d . . . F3 F 0.3733(6) -0.1290(3) 0.3148(3) 0.0997(16) Uani 1 1 d . . . F4 F 0.3436(4) -0.0425(3) 0.1825(2) 0.0775(12) Uani 1 1 d . . . F5 F 0.3658(7) 0.1293(3) 0.2211(3) 0.116(2) Uani 1 1 d . . . F6 F 0.5216(4) -0.0163(4) 0.2192(3) 0.0972(15) Uani 1 1 d . . . P1 P 0.71794(9) 0.60321(8) -0.04565(6) 0.0126(2) Uani 1 1 d . . . P2 P 0.87444(9) 0.43229(8) -0.15926(6) 0.0130(2) Uani 1 1 d . . . P3 P 0.67411(10) 0.29841(8) 0.35683(6) 0.0169(2) Uani 1 1 d . . . P4 P 0.57277(10) 0.77939(8) 0.50758(6) 0.0155(2) Uani 1 1 d . . . P5 P 0.36032(13) 0.00046(11) 0.26978(8) 0.0337(3) Uani 1 1 d . . . S1 S 0.96204(9) 0.47951(8) 0.19666(6) 0.0183(2) Uani 1 1 d . . . S2 S 0.58036(9) 0.44732(8) 0.32099(6) 0.0190(2) Uani 1 1 d . . . Cu1 Cu 0.74964(4) 0.57607(4) 0.25016(3) 0.01580(15) Uani 1 1 d . . . 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 C1 0.0166(18) 0.0117(17) 0.0144(16) -0.0015(13) -0.0029(14) -0.0005(14) C2 0.0176(18) 0.0160(18) 0.0130(16) -0.0018(14) -0.0018(14) -0.0011(14) C3 0.0140(18) 0.022(2) 0.0249(19) -0.0115(16) -0.0066(15) 0.0022(15) C4 0.0152(18) 0.0169(19) 0.0165(17) -0.0060(14) 0.0008(14) 0.0000(15) C5 0.023(2) 0.0150(19) 0.0196(18) -0.0050(15) -0.0072(16) 0.0047(15) C6 0.0185(19) 0.0133(18) 0.0151(16) -0.0022(14) -0.0043(14) -0.0041(14) C7 0.0170(19) 0.023(2) 0.025(2) 0.0040(16) -0.0052(16) -0.0060(16) C8 0.031(2) 0.022(2) 0.038(2) -0.0022(18) -0.0061(19) -0.0060(18) C9 0.026(2) 0.019(2) 0.0197(18) -0.0015(15) -0.0111(16) 0.0033(16) C10 0.042(3) 0.033(2) 0.029(2) -0.0107(19) -0.021(2) 0.004(2) C11 0.0177(19) 0.0142(18) 0.0129(16) -0.0036(14) 0.0000(14) -0.0023(14) C12 0.022(2) 0.0124(18) 0.0158(17) -0.0020(14) -0.0032(15) -0.0004(15) C13 0.029(2) 0.0165(19) 0.0136(17) -0.0023(14) -0.0069(15) 0.0032(16) C14 0.0200(19) 0.0166(19) 0.0109(16) -0.0017(14) -0.0016(14) -0.0027(15) C15 0.024(2) 0.023(2) 0.0209(19) -0.0045(16) -0.0084(16) -0.0030(16) C16 0.0196(19) 0.0178(19) 0.0158(17) -0.0043(14) -0.0041(15) 0.0040(15) C17 0.032(2) 0.040(3) 0.028(2) -0.018(2) -0.0039(19) -0.003(2) C18 0.049(3) 0.029(2) 0.026(2) -0.0146(19) -0.004(2) 0.004(2) C19 0.158(8) 0.066(4) 0.039(3) 0.003(3) -0.048(4) -0.052(5) C20 0.109(6) 0.184(10) 0.044(3) -0.012(5) -0.012(4) -0.104(7) N1 0.0152(15) 0.0115(15) 0.0115(13) -0.0017(11) -0.0025(11) -0.0008(12) N2 0.0201(16) 0.0130(15) 0.0148(14) -0.0025(12) -0.0044(12) -0.0012(12) N3 0.0162(16) 0.0176(16) 0.0180(15) -0.0089(12) -0.0034(12) 0.0025(13) N4 0.0123(15) 0.0174(16) 0.0178(14) -0.0075(12) -0.0021(12) -0.0004(12) N5 0.0160(16) 0.0137(15) 0.0108(14) -0.0032(11) 0.0005(12) 0.0007(12) N6 0.0207(17) 0.0165(16) 0.0139(14) -0.0032(12) -0.0009(12) -0.0031(13) N7 0.0235(17) 0.0205(17) 0.0153(15) -0.0059(13) -0.0062(13) 0.0031(14) N8 0.0273(18) 0.0104(16) 0.0175(15) -0.0010(12) 0.0052(14) 0.0022(13) O1 0.0176(13) 0.0163(13) 0.0225(13) 0.0024(10) -0.0085(11) -0.0032(10) O2 0.0237(14) 0.0140(13) 0.0148(12) -0.0050(10) -0.0087(11) 0.0032(10) O3 0.0234(14) 0.0190(14) 0.0143(12) -0.0066(10) 0.0019(11) -0.0015(11) O4 0.0315(16) 0.0256(15) 0.0213(13) -0.0069(11) -0.0107(12) 0.0041(12) F1 0.133(3) 0.056(2) 0.0503(19) -0.0310(16) -0.054(2) 0.023(2) F2 0.041(3) 0.285(9) 0.226(7) -0.156(7) 0.002(4) 0.019(4) F3 0.191(5) 0.041(2) 0.063(2) -0.0004(18) -0.039(3) -0.010(3) F4 0.102(3) 0.090(3) 0.069(2) -0.028(2) -0.057(2) -0.008(2) F5 0.239(6) 0.045(2) 0.104(3) 0.004(2) -0.117(4) 0.009(3) F6 0.057(2) 0.126(4) 0.114(3) -0.073(3) -0.007(2) -0.009(2) P1 0.0109(4) 0.0136(5) 0.0125(4) -0.0038(3) -0.0021(3) -0.0002(3) P2 0.0137(5) 0.0127(5) 0.0122(4) -0.0034(3) -0.0036(3) 0.0006(3) P3 0.0221(5) 0.0114(5) 0.0123(4) -0.0026(3) 0.0008(4) 0.0007(4) P4 0.0218(5) 0.0093(4) 0.0105(4) -0.0012(3) 0.0003(4) 0.0011(4) P5 0.0459(7) 0.0318(7) 0.0294(6) -0.0113(5) -0.0201(5) 0.0079(5) S1 0.0124(4) 0.0163(5) 0.0228(5) -0.0054(4) -0.0001(4) -0.0005(3) S2 0.0180(5) 0.0116(4) 0.0219(5) 0.0016(3) -0.0010(4) -0.0013(4) Cu1 0.0182(3) 0.0144(3) 0.0122(2) -0.00268(17) -0.00107(18) -0.00119(18) _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 C1 N1 1.494(4) . ? C1 P1 1.813(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.480(4) . ? C2 P1 1.828(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N3 1.481(4) . ? C3 P1 1.811(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.463(5) . ? C4 N1 1.489(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N3 1.465(5) . ? C5 N2 1.467(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N2 1.459(4) . ? C6 N1 1.499(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O1 1.470(4) . ? C7 C8 1.494(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O2 1.453(4) . ? C9 C10 1.495(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N5 1.496(4) . ? C11 P4 1.818(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N6 1.482(4) . ? C12 P4 1.810(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N7 1.482(5) . ? C13 P4 1.818(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N6 1.461(4) . ? C14 N5 1.493(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N6 1.468(5) . ? C15 N7 1.475(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N7 1.463(4) . ? C16 N5 1.485(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.453(5) . ? C17 C18 1.491(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.316(9) . ? C19 O4 1.623(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 Cu1 2.176(3) . ? N4 P1 1.590(3) . ? N4 P2 1.602(3) . ? N5 Cu1 2.131(3) . ? N8 P4 1.576(3) 2_666 ? N8 P3 1.593(3) . ? O1 P2 1.584(3) . ? O2 P2 1.587(2) . ? O3 P3 1.583(2) . ? O4 P3 1.578(3) . ? F1 P5 1.583(3) . ? F2 P5 1.504(5) . ? F3 P5 1.569(4) . ? F4 P5 1.583(3) . ? F5 P5 1.568(4) . ? F6 P5 1.605(4) . ? P2 S1 1.9689(13) 2_765 ? P3 S2 1.9856(13) . ? P4 N8 1.576(3) 2_666 ? S1 P2 1.9689(13) 2_765 ? S1 Cu1 2.3142(10) . ? S2 Cu1 2.3200(10) . ? 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 N1 C1 P1 111.3(2) . . ? N1 C1 H1A 109.4 . . ? P1 C1 H1A 109.4 . . ? N1 C1 H1B 109.4 . . ? P1 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? N2 C2 P1 107.9(2) . . ? N2 C2 H2A 110.1 . . ? P1 C2 H2A 110.1 . . ? N2 C2 H2B 110.1 . . ? P1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? N3 C3 P1 109.1(2) . . ? N3 C3 H3A 109.9 . . ? P1 C3 H3A 109.9 . . ? N3 C3 H3B 109.9 . . ? P1 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N3 C4 N1 114.7(3) . . ? N3 C4 H4A 108.6 . . ? N1 C4 H4A 108.6 . . ? N3 C4 H4B 108.6 . . ? N1 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? N3 C5 N2 113.5(3) . . ? N3 C5 H5A 108.9 . . ? N2 C5 H5A 108.9 . . ? N3 C5 H5B 108.9 . . ? N2 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N2 C6 N1 114.3(3) . . ? N2 C6 H6A 108.7 . . ? N1 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? N1 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C8 108.2(3) . . ? O1 C7 H7A 110.1 . . ? C8 C7 H7A 110.1 . . ? O1 C7 H7B 110.1 . . ? C8 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C10 107.1(3) . . ? O2 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? O2 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N5 C11 P4 110.8(2) . . ? N5 C11 H11A 109.5 . . ? P4 C11 H11A 109.5 . . ? N5 C11 H11B 109.5 . . ? P4 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N6 C12 P4 109.0(2) . . ? N6 C12 H12A 109.9 . . ? P4 C12 H12A 109.9 . . ? N6 C12 H12B 109.9 . . ? P4 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? N7 C13 P4 108.9(2) . . ? N7 C13 H13A 109.9 . . ? P4 C13 H13A 109.9 . . ? N7 C13 H13B 109.9 . . ? P4 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? N6 C14 N5 114.3(3) . . ? N6 C14 H14A 108.7 . . ? N5 C14 H14A 108.7 . . ? N6 C14 H14B 108.7 . . ? N5 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N6 C15 N7 114.0(3) . . ? N6 C15 H15A 108.8 . . ? N7 C15 H15A 108.8 . . ? N6 C15 H15B 108.8 . . ? N7 C15 H15B 108.8 . . ? H15A C15 H15B 107.6 . . ? N7 C16 N5 115.1(3) . . ? N7 C16 H16A 108.5 . . ? N5 C16 H16A 108.5 . . ? N7 C16 H16B 108.5 . . ? N5 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? O3 C17 C18 108.0(4) . . ? O3 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? O3 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 O4 101.0(7) . . ? C20 C19 H19A 111.6 . . ? O4 C19 H19A 111.6 . . ? C20 C19 H19B 111.6 . . ? O4 C19 H19B 111.6 . . ? H19A C19 H19B 109.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 N1 C1 109.4(3) . . ? C4 N1 C6 108.2(3) . . ? C1 N1 C6 109.2(3) . . ? C4 N1 Cu1 114.1(2) . . ? C1 N1 Cu1 104.6(2) . . ? C6 N1 Cu1 111.3(2) . . ? C6 N2 C5 109.4(3) . . ? C6 N2 C2 112.2(3) . . ? C5 N2 C2 112.2(3) . . ? C4 N3 C5 109.3(3) . . ? C4 N3 C3 112.1(3) . . ? C5 N3 C3 111.0(3) . . ? P1 N4 P2 127.03(19) . . ? C16 N5 C14 107.9(3) . . ? C16 N5 C11 109.8(3) . . ? C14 N5 C11 110.0(3) . . ? C16 N5 Cu1 106.7(2) . . ? C14 N5 Cu1 112.24(19) . . ? C11 N5 Cu1 110.2(2) . . ? C14 N6 C15 109.0(3) . . ? C14 N6 C12 112.0(3) . . ? C15 N6 C12 111.7(3) . . ? C16 N7 C15 108.5(3) . . ? C16 N7 C13 112.1(3) . . ? C15 N7 C13 111.2(3) . . ? P4 N8 P3 128.8(2) 2_666 . ? C7 O1 P2 121.7(2) . . ? C9 O2 P2 121.4(2) . . ? C17 O3 P3 120.5(2) . . ? P3 O4 C19 125.7(3) . . ? N4 P1 C3 111.88(16) . . ? N4 P1 C1 115.17(16) . . ? C3 P1 C1 101.21(17) . . ? N4 P1 C2 123.36(16) . . ? C3 P1 C2 101.28(17) . . ? C1 P1 C2 100.91(16) . . ? O1 P2 O2 99.84(13) . . ? O1 P2 N4 112.26(15) . . ? O2 P2 N4 106.00(15) . . ? O1 P2 S1 108.80(11) . 2_765 ? O2 P2 S1 114.65(11) . 2_765 ? N4 P2 S1 114.41(12) . 2_765 ? O4 P3 O3 101.11(15) . . ? O4 P3 N8 111.47(17) . . ? O3 P3 N8 107.10(15) . . ? O4 P3 S2 108.76(12) . . ? O3 P3 S2 113.19(11) . . ? N8 P3 S2 114.44(13) . . ? N8 P4 C12 114.24(17) 2_666 . ? N8 P4 C11 116.13(17) 2_666 . ? C12 P4 C11 100.76(16) . . ? N8 P4 C13 120.06(17) 2_666 . ? C12 P4 C13 101.79(18) . . ? C11 P4 C13 101.05(17) . . ? F2 P5 F5 92.7(4) . . ? F2 P5 F3 93.8(4) . . ? F5 P5 F3 173.4(3) . . ? F2 P5 F4 92.6(3) . . ? F5 P5 F4 90.7(2) . . ? F3 P5 F4 90.3(2) . . ? F2 P5 F1 92.4(3) . . ? F5 P5 F1 87.5(2) . . ? F3 P5 F1 90.9(2) . . ? F4 P5 F1 174.8(2) . . ? F2 P5 F6 179.0(3) . . ? F5 P5 F6 88.2(3) . . ? F3 P5 F6 85.3(3) . . ? F4 P5 F6 86.7(2) . . ? F1 P5 F6 88.3(2) . . ? P2 S1 Cu1 119.10(5) 2_765 . ? P3 S2 Cu1 105.91(5) . . ? N5 Cu1 N1 117.92(11) . . ? N5 Cu1 S1 114.77(9) . . ? N1 Cu1 S1 103.77(8) . . ? N5 Cu1 S2 105.16(8) . . ? N1 Cu1 S2 103.02(8) . . ? S1 Cu1 S2 111.71(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 N1 C1 -66.3(4) . . . . ? N3 C4 N1 C6 52.5(4) . . . . ? N3 C4 N1 Cu1 176.9(2) . . . . ? P1 C1 N1 C4 59.0(3) . . . . ? P1 C1 N1 C6 -59.2(3) . . . . ? P1 C1 N1 Cu1 -178.42(16) . . . . ? N2 C6 N1 C4 -52.7(3) . . . . ? N2 C6 N1 C1 66.3(4) . . . . ? N2 C6 N1 Cu1 -178.7(2) . . . . ? N1 C6 N2 C5 55.0(4) . . . . ? N1 C6 N2 C2 -70.2(4) . . . . ? N3 C5 N2 C6 -56.3(4) . . . . ? N3 C5 N2 C2 68.8(4) . . . . ? P1 C2 N2 C6 62.6(3) . . . . ? P1 C2 N2 C5 -61.0(3) . . . . ? N1 C4 N3 C5 -54.7(4) . . . . ? N1 C4 N3 C3 68.9(4) . . . . ? N2 C5 N3 C4 55.9(4) . . . . ? N2 C5 N3 C3 -68.3(4) . . . . ? P1 C3 N3 C4 -61.0(3) . . . . ? P1 C3 N3 C5 61.6(3) . . . . ? N7 C16 N5 C14 53.7(4) . . . . ? N7 C16 N5 C11 -66.1(4) . . . . ? N7 C16 N5 Cu1 174.5(2) . . . . ? N6 C14 N5 C16 -53.7(4) . . . . ? N6 C14 N5 C11 66.0(4) . . . . ? N6 C14 N5 Cu1 -170.9(2) . . . . ? P4 C11 N5 C16 59.2(3) . . . . ? P4 C11 N5 C14 -59.3(3) . . . . ? P4 C11 N5 Cu1 176.48(15) . . . . ? N5 C14 N6 C15 55.4(4) . . . . ? N5 C14 N6 C12 -68.6(4) . . . . ? N7 C15 N6 C14 -56.2(4) . . . . ? N7 C15 N6 C12 68.1(4) . . . . ? P4 C12 N6 C14 62.1(3) . . . . ? P4 C12 N6 C15 -60.4(3) . . . . ? N5 C16 N7 C15 -54.8(4) . . . . ? N5 C16 N7 C13 68.3(4) . . . . ? N6 C15 N7 C16 55.5(4) . . . . ? N6 C15 N7 C13 -68.2(4) . . . . ? P4 C13 N7 C16 -60.9(3) . . . . ? P4 C13 N7 C15 60.7(3) . . . . ? C8 C7 O1 P2 132.3(3) . . . . ? C10 C9 O2 P2 -178.7(3) . . . . ? C18 C17 O3 P3 -161.1(3) . . . . ? C20 C19 O4 P3 -67.0(5) . . . . ? P2 N4 P1 C3 175.2(2) . . . . ? P2 N4 P1 C1 -70.0(3) . . . . ? P2 N4 P1 C2 54.1(3) . . . . ? N3 C3 P1 N4 174.0(2) . . . . ? N3 C3 P1 C1 50.9(3) . . . . ? N3 C3 P1 C2 -52.8(3) . . . . ? N1 C1 P1 N4 -172.4(2) . . . . ? N1 C1 P1 C3 -51.5(3) . . . . ? N1 C1 P1 C2 52.4(3) . . . . ? N2 C2 P1 N4 177.8(2) . . . . ? N2 C2 P1 C3 51.9(3) . . . . ? N2 C2 P1 C1 -52.0(3) . . . . ? C7 O1 P2 O2 -51.8(3) . . . . ? C7 O1 P2 N4 60.1(3) . . . . ? C7 O1 P2 S1 -172.2(2) . . . 2_765 ? C9 O2 P2 O1 168.4(3) . . . . ? C9 O2 P2 N4 51.6(3) . . . . ? C9 O2 P2 S1 -75.6(3) . . . 2_765 ? P1 N4 P2 O1 94.5(3) . . . . ? P1 N4 P2 O2 -157.5(2) . . . . ? P1 N4 P2 S1 -30.1(3) . . . 2_765 ? C19 O4 P3 O3 -27.0(4) . . . . ? C19 O4 P3 N8 86.5(4) . . . . ? C19 O4 P3 S2 -146.4(3) . . . . ? C17 O3 P3 O4 168.3(3) . . . . ? C17 O3 P3 N8 51.5(3) . . . . ? C17 O3 P3 S2 -75.6(3) . . . . ? P4 N8 P3 O4 95.1(3) 2_666 . . . ? P4 N8 P3 O3 -155.2(2) 2_666 . . . ? P4 N8 P3 S2 -28.9(3) 2_666 . . . ? N6 C12 P4 N8 -177.5(2) . . . 2_666 ? N6 C12 P4 C11 -52.2(3) . . . . ? N6 C12 P4 C13 51.6(3) . . . . ? N5 C11 P4 N8 176.2(2) . . . 2_666 ? N5 C11 P4 C12 52.3(3) . . . . ? N5 C11 P4 C13 -52.2(3) . . . . ? N7 C13 P4 N8 -179.2(2) . . . 2_666 ? N7 C13 P4 C12 -52.0(3) . . . . ? N7 C13 P4 C11 51.6(3) . . . . ? O4 P3 S2 Cu1 45.50(12) . . . . ? O3 P3 S2 Cu1 -66.02(12) . . . . ? N8 P3 S2 Cu1 170.89(13) . . . . ? C16 N5 Cu1 N1 -151.5(2) . . . . ? C14 N5 Cu1 N1 -33.5(3) . . . . ? C11 N5 Cu1 N1 89.4(2) . . . . ? C16 N5 Cu1 S1 -28.7(2) . . . . ? C14 N5 Cu1 S1 89.3(2) . . . . ? C11 N5 Cu1 S1 -147.8(2) . . . . ? C16 N5 Cu1 S2 94.5(2) . . . . ? C14 N5 Cu1 S2 -147.6(2) . . . . ? C11 N5 Cu1 S2 -24.6(2) . . . . ? C4 N1 Cu1 N5 -66.3(2) . . . . ? C1 N1 Cu1 N5 174.20(19) . . . . ? C6 N1 Cu1 N5 56.4(2) . . . . ? C4 N1 Cu1 S1 165.5(2) . . . . ? C1 N1 Cu1 S1 46.0(2) . . . . ? C6 N1 Cu1 S1 -71.7(2) . . . . ? C4 N1 Cu1 S2 48.9(2) . . . . ? C1 N1 Cu1 S2 -70.6(2) . . . . ? C6 N1 Cu1 S2 171.68(19) . . . . ? P2 S1 Cu1 N5 -46.98(11) 2_765 . . . ? P2 S1 Cu1 N1 83.11(9) 2_765 . . . ? P2 S1 Cu1 S2 -166.57(5) 2_765 . . . ? P3 S2 Cu1 N5 -103.98(9) . . . . ? P3 S2 Cu1 N1 131.93(8) . . . . ? P3 S2 Cu1 S1 21.13(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.232 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.168 #===END #=============================================================================== data_7a _database_code_depnum_ccdc_archive 'CCDC 785088' #TrackingRef '- 3_7a.cif' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 I N3 S' _chemical_formula_sum 'C15 H12 I N3 S' _chemical_formula_weight 393.24 _chemical_compound_source synthesis loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.5177(2) _cell_length_b 7.2359(1) _cell_length_c 14.3593(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.588(2) _cell_angle_gamma 90.00 _cell_volume 1477.68(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4277 _cell_measurement_theta_min 3.1028 _cell_measurement_theta_max 73.7570 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1982 _exptl_crystal_size_mid 0.1123 _exptl_crystal_size_min 0.0555 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 18.284 _exptl_absorpt_correction_T_min 0.26392 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_device ; 165 mm Onyx CCD detector in \k-geometry diffractometer ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.2640 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6667 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 73.87 _reflns_number_total 2903 _reflns_number_gt 2438 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SIR2004(Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0748P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2903 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _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 C1 C -0.1324(2) 0.2005(5) 0.0295(3) 0.0191(7) Uani 1 1 d . . . C2 C -0.2270(3) 0.2493(4) 0.0235(4) 0.0260(10) Uani 1 1 d . . . C3 C -0.2843(3) 0.2682(5) -0.0651(4) 0.0351(11) Uani 1 1 d . . . C4 C -0.2497(4) 0.2443(5) -0.1467(4) 0.0338(12) Uani 1 1 d . . . C5 C -0.1567(3) 0.1931(6) -0.1415(3) 0.0289(8) Uani 1 1 d . . . C6 C -0.0977(2) 0.1706(5) -0.0528(2) 0.0225(7) Uani 1 1 d . . . C7 C 0.0209(2) 0.3784(5) 0.1401(2) 0.0195(6) Uani 1 1 d . . . C8 C 0.1927(3) 0.2749(4) 0.1717(3) 0.0162(7) Uani 1 1 d . . . C9 C 0.2542(3) 0.2501(4) 0.1114(3) 0.0155(8) Uani 1 1 d . . . C10 C 0.3547(2) 0.2002(5) 0.1272(2) 0.0203(7) Uani 1 1 d . . . C11 C 0.4011(2) 0.1059(5) 0.2081(2) 0.0239(7) Uani 1 1 d . . . C12 C 0.4952(2) 0.0592(6) 0.2183(3) 0.0315(9) Uani 1 1 d . . . C13 C 0.5439(2) 0.1045(7) 0.1490(3) 0.0404(10) Uani 1 1 d . . . C14 C 0.5001(3) 0.2014(8) 0.0690(4) 0.0482(12) Uani 1 1 d . . . C15 C 0.4053(3) 0.2506(5) 0.0588(4) 0.0321(12) Uani 1 1 d . . . N1 N 0.11065(16) 0.3290(4) 0.11546(16) 0.0153(5) Uani 1 1 d . . . N2 N 0.11894(17) 0.3347(4) 0.02382(17) 0.0186(6) Uani 1 1 d . . . N3 N 0.2057(2) 0.2876(4) 0.0219(2) 0.0193(6) Uani 1 1 d . . . S1 S -0.05780(5) 0.18497(13) 0.14343(5) 0.0210(2) Uani 1 1 d . . . I1 I 0.204429(15) 0.25078(2) 0.318962(15) 0.01694(13) Uani 1 1 d . . . H2 H -0.247(3) 0.270(4) 0.085(3) 0.025(12) Uiso 1 1 d . . . H3 H -0.351(4) 0.315(7) -0.070(3) 0.056(14) Uiso 1 1 d . . . H4 H -0.285(4) 0.261(5) -0.216(5) 0.05(2) Uiso 1 1 d . . . H5 H -0.127(3) 0.174(6) -0.201(3) 0.030(10) Uiso 1 1 d . . . H6 H -0.034(3) 0.122(6) -0.048(3) 0.061(14) Uiso 1 1 d . . . H7A H -0.007(2) 0.479(6) 0.094(3) 0.040(11) Uiso 1 1 d . . . H7B H 0.028(3) 0.430(6) 0.203(3) 0.043(12) Uiso 1 1 d . . . H11 H 0.366(2) 0.072(5) 0.256(2) 0.027(10) Uiso 1 1 d . . . H12 H 0.525(3) -0.007(5) 0.273(3) 0.033(11) Uiso 1 1 d . . . H13 H 0.611(3) 0.072(6) 0.154(3) 0.052(12) Uiso 1 1 d . . . H14 H 0.531(4) 0.240(4) 0.017(4) 0.032(15) Uiso 1 1 d . . . H15 H 0.378(3) 0.302(6) -0.001(3) 0.035(12) Uiso 1 1 d . . . 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 C1 0.0212(15) 0.0140(16) 0.0225(17) 0.0004(15) 0.0054(13) -0.0021(14) C2 0.020(2) 0.026(2) 0.032(3) -0.0034(13) 0.0061(18) -0.0005(11) C3 0.022(2) 0.035(3) 0.044(3) -0.0016(17) -0.0051(19) -0.0010(14) C4 0.038(3) 0.026(3) 0.028(2) 0.0073(14) -0.013(2) -0.0107(13) C5 0.040(2) 0.026(2) 0.0187(17) 0.0011(17) 0.0007(15) -0.0145(19) C6 0.0262(16) 0.022(2) 0.0201(15) -0.0006(14) 0.0062(13) -0.0034(14) C7 0.0239(15) 0.0180(18) 0.0153(13) 0.0021(13) 0.0008(12) 0.0033(13) C8 0.0237(17) 0.0123(17) 0.0107(16) 0.0038(11) -0.0011(14) -0.0010(11) C9 0.0176(18) 0.0139(19) 0.0127(18) -0.0003(10) -0.0021(15) -0.0025(10) C10 0.0178(15) 0.0208(17) 0.0206(16) -0.0061(15) -0.0005(13) -0.0012(14) C11 0.0206(15) 0.0202(18) 0.0289(16) -0.0019(15) 0.0005(13) 0.0004(13) C12 0.0233(16) 0.027(2) 0.039(2) -0.0106(17) -0.0056(16) 0.0075(14) C13 0.0171(15) 0.058(3) 0.043(2) -0.020(2) -0.0002(16) 0.0066(17) C14 0.024(2) 0.089(4) 0.032(2) -0.016(3) 0.0070(18) -0.003(2) C15 0.022(2) 0.054(3) 0.020(2) -0.0062(15) 0.0029(18) -0.0034(14) N1 0.0170(11) 0.0176(15) 0.0097(11) 0.0003(11) -0.0010(9) -0.0012(10) N2 0.0226(13) 0.0182(16) 0.0140(11) 0.0010(11) 0.0013(10) -0.0028(10) N3 0.0203(14) 0.0237(16) 0.0129(14) -0.0003(12) 0.0006(11) -0.0044(11) S1 0.0223(4) 0.0260(5) 0.0150(4) 0.0034(4) 0.0047(3) -0.0001(3) I1 0.01997(18) 0.0198(2) 0.00930(18) 0.00033(6) -0.00125(12) 0.00195(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C6 1.391(5) . ? C1 C2 1.404(5) . ? C1 S1 1.774(4) . ? C2 C3 1.380(7) . ? C2 H2 1.00(5) . ? C3 C4 1.376(8) . ? C3 H3 1.01(5) . ? C4 C5 1.387(7) . ? C4 H4 1.03(7) . ? C5 C6 1.395(5) . ? C5 H5 1.05(4) . ? C6 H6 0.98(5) . ? C7 N1 1.461(4) . ? C7 S1 1.814(4) . ? C7 H7A 1.01(4) . ? C7 H7B 0.96(4) . ? C8 N1 1.356(4) . ? C8 C9 1.373(5) . ? C8 I1 2.094(4) . ? C9 N3 1.364(5) . ? C9 C10 1.477(5) . ? C10 C15 1.389(6) . ? C10 C11 1.397(5) . ? C11 C12 1.386(5) . ? C11 H11 0.97(3) . ? C12 C13 1.372(6) . ? C12 H12 0.95(4) . ? C13 C14 1.387(7) . ? C13 H13 0.98(4) . ? C14 C15 1.400(6) . ? C14 H14 0.98(5) . ? C15 H15 0.95(4) . ? N1 N2 1.346(3) . ? N2 N3 1.311(4) . ? 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 C6 C1 C2 120.2(4) . . ? C6 C1 S1 121.0(3) . . ? C2 C1 S1 118.8(3) . . ? C3 C2 C1 118.9(4) . . ? C3 C2 H2 125(3) . . ? C1 C2 H2 116(3) . . ? C4 C3 C2 121.1(5) . . ? C4 C3 H3 119(3) . . ? C2 C3 H3 119(3) . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 128(4) . . ? C5 C4 H4 112(4) . . ? C4 C5 C6 119.5(4) . . ? C4 C5 H5 124(2) . . ? C6 C5 H5 117(2) . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 120(2) . . ? C5 C6 H6 120(2) . . ? N1 C7 S1 114.5(2) . . ? N1 C7 H7A 106.5(19) . . ? S1 C7 H7A 113(2) . . ? N1 C7 H7B 113(2) . . ? S1 C7 H7B 103(2) . . ? H7A C7 H7B 106(3) . . ? N1 C8 C9 105.5(3) . . ? N1 C8 I1 120.6(3) . . ? C9 C8 I1 134.0(3) . . ? N3 C9 C8 106.9(3) . . ? N3 C9 C10 120.0(3) . . ? C8 C9 C10 133.0(3) . . ? C15 C10 C11 118.8(3) . . ? C15 C10 C9 118.3(3) . . ? C11 C10 C9 122.9(3) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 121(2) . . ? C10 C11 H11 119(2) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 121(2) . . ? C11 C12 H12 119(2) . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 122(2) . . ? C14 C13 H13 117(2) . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 125(3) . . ? C15 C14 H14 116(3) . . ? C10 C15 C14 120.5(4) . . ? C10 C15 H15 124(3) . . ? C14 C15 H15 114(3) . . ? N2 N1 C8 110.5(3) . . ? N2 N1 C7 119.2(2) . . ? C8 N1 C7 130.3(3) . . ? N3 N2 N1 106.7(2) . . ? N2 N3 C9 110.3(3) . . ? C1 S1 C7 101.41(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(5) . . . . ? S1 C1 C2 C3 177.6(3) . . . . ? C1 C2 C3 C4 -1.5(5) . . . . ? C2 C3 C4 C5 2.6(6) . . . . ? C3 C4 C5 C6 -1.7(6) . . . . ? C2 C1 C6 C5 1.3(6) . . . . ? S1 C1 C6 C5 -176.7(3) . . . . ? C4 C5 C6 C1 -0.3(6) . . . . ? N1 C8 C9 N3 -0.9(3) . . . . ? I1 C8 C9 N3 -179.6(2) . . . . ? N1 C8 C9 C10 177.0(3) . . . . ? I1 C8 C9 C10 -1.8(5) . . . . ? N3 C9 C10 C15 21.1(5) . . . . ? C8 C9 C10 C15 -156.6(3) . . . . ? N3 C9 C10 C11 -159.4(3) . . . . ? C8 C9 C10 C11 23.0(6) . . . . ? C15 C10 C11 C12 -1.8(5) . . . . ? C9 C10 C11 C12 178.7(3) . . . . ? C10 C11 C12 C13 -0.2(6) . . . . ? C11 C12 C13 C14 1.6(7) . . . . ? C12 C13 C14 C15 -0.9(7) . . . . ? C11 C10 C15 C14 2.4(6) . . . . ? C9 C10 C15 C14 -178.0(4) . . . . ? C13 C14 C15 C10 -1.1(7) . . . . ? C9 C8 N1 N2 1.2(3) . . . . ? I1 C8 N1 N2 -179.9(2) . . . . ? C9 C8 N1 C7 -178.8(3) . . . . ? I1 C8 N1 C7 0.1(5) . . . . ? S1 C7 N1 N2 92.0(3) . . . . ? S1 C7 N1 C8 -88.0(4) . . . . ? C8 N1 N2 N3 -0.9(4) . . . . ? C7 N1 N2 N3 179.0(3) . . . . ? N1 N2 N3 C9 0.3(3) . . . . ? C8 C9 N3 N2 0.4(3) . . . . ? C10 C9 N3 N2 -177.8(3) . . . . ? C6 C1 S1 C7 65.9(3) . . . . ? C2 C1 S1 C7 -112.1(3) . . . . ? N1 C7 S1 C1 -97.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 73.87 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.928 _refine_diff_density_min -1.786 _refine_diff_density_rms 0.161 #===END