# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_ #5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Kurt Mereiter Department of Chemistry Vienna University of Technology Getreidemarkt 9 A-1060 Vienna Austria ; _publ_contact_author_phone '++43 1 58801-17111' _publ_contact_author_fax '++43 1 58801-17199' _publ_contact_author_email Kurt.Mereiter@tuwien.ac.at _publ_contact_letter ; Dear CCDC team, Intended title of the paper: Tri- and Tetracoordinate Copper(I) Complexes bearing Bidentate Soft/Hard SN and SeN Ligands based on 2-Aminopyridine Authors: \"Ozg\"ur \"Oztopcu, Kurt Mereiter, Michael Puchberger, Karl Kirchner Institution were X-ray work was carried out: Department of Chemistry Vienna University of Technology Getreidemarkt 9 A-1060 Vienna Austria Some explanatory remarks on each compound are given in #_exptl_special_details We ask for CCDC numbers. Best wishes, Kurt Mereiter ; _publ_contact_author_name 'Kurt Mereiter' loop_ _publ_author_name 'Ozgur Oztopcu' 'Kurt Mereiter' 'Michael Puchberger' 'Karl Kirchner' #=============================================================================== # Cu-EPN-paper, 15 Structures, version of 28.1.2011 # Structure and chemical codes. # 1a-1463 SPN-Ph # 1b-1462 SPN-iPr # 2a-1457 SePN-Ph # 2b-1475 SePN-iPr # 3a-1442 [CuBr(SPN-Ph)] # 3b-1449 [CuBr(SPN-iPr)] # 5b-1480 [CuI(SPN-iPr)] # 6b-1459 [CuI(SePN-iPr)] # 7a-1528 [Cu(NHC)(SPN-Ph)]SbF6.((CH3)2CO) # 7b-1529 [Cu(NHC)(SPN-iPr)]SbF6 # 8b-1476 [Cu(SPN-iPr)2]PF6 # 11a-1499 [Cu2(SPN-Ph)2(CH3CN)2](SbF6)2.2(Et2O) # 11b-1477 [Cu2(SPN-iPr)2(CH3CN)2](SbF6)2 # 12-1505 [Cu2(SPN-iPr)2(CN-tBu)2](SbF6)2.2(Et2O) # 13-1512 [Cu(CF3SO3)(SPN-iPr)(PPh3)] #=============================================================================80 # 1463 SPN-Ph data_1a-1463 _database_code_depnum_ccdc_archive 'CCDC 810363' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480_ #6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1463 SPN-Ph at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N2 P S' _chemical_formula_sum 'C17 H15 N2 P S' _chemical_formula_weight 310.34 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.4734(10) _cell_length_b 13.0561(11) _cell_length_c 19.8602(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.388(1) _cell_angle_gamma 90.00 _cell_volume 3207.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9071 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 29.99 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Prismatic crystals from ethanol by evaporation. Bruker Smart APEX CCD 3-axis diffractometer. The structure contains two independent molecules which differ significantly in conformation. The compound is isostructural with the corresponding Se compound, 2a-1457, in this CIF. ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 47406 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9339 _reflns_number_gt 8341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0539P)^2^+1.2643P] 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 9339 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 S1 S 0.02033(2) 0.86425(2) 0.403071(16) 0.02672(7) Uani 1 1 d . . . P1 P 0.12523(2) 0.78706(2) 0.464143(14) 0.01670(6) Uani 1 1 d . . . N1 N 0.41889(7) 0.88803(7) 0.45829(4) 0.01608(16) Uani 1 1 d . . . N2 N 0.25094(7) 0.83323(7) 0.47748(5) 0.01850(17) Uani 1 1 d . . . H2N H 0.2746 0.8497 0.5198 0.022 Uiso 1 1 calc R . . C1 C 0.32356(8) 0.84927(8) 0.43075(5) 0.01624(18) Uani 1 1 d . . . C2 C 0.30147(9) 0.82421(9) 0.36167(5) 0.0200(2) Uani 1 1 d . . . H2 H 0.2328 0.7983 0.3432 0.024 Uiso 1 1 calc R . . C3 C 0.38281(10) 0.83843(9) 0.32128(5) 0.0213(2) Uani 1 1 d . . . H3 H 0.3707 0.8213 0.2744 0.026 Uiso 1 1 calc R . . C4 C 0.48235(9) 0.87776(8) 0.34933(6) 0.0204(2) Uani 1 1 d . . . H4 H 0.5391 0.8877 0.3224 0.025 Uiso 1 1 calc R . . C5 C 0.49598(8) 0.90197(8) 0.41776(5) 0.01785(19) Uani 1 1 d . . . H5 H 0.5633 0.9299 0.4370 0.021 Uiso 1 1 calc R . . C6 C 0.13652(9) 0.65514(8) 0.43813(5) 0.01909(19) Uani 1 1 d . . . C7 C 0.04126(10) 0.59885(10) 0.42354(7) 0.0287(2) Uani 1 1 d . . . H7 H -0.0267 0.6308 0.4256 0.034 Uiso 1 1 calc R . . C8 C 0.04589(13) 0.49595(11) 0.40593(8) 0.0380(3) Uani 1 1 d . . . H8 H -0.0189 0.4574 0.3968 0.046 Uiso 1 1 calc R . . C9 C 0.14481(14) 0.44944(10) 0.40165(7) 0.0379(3) Uani 1 1 d . . . H9 H 0.1474 0.3795 0.3887 0.045 Uiso 1 1 calc R . . C10 C 0.23964(13) 0.50458(10) 0.41623(7) 0.0352(3) Uani 1 1 d . . . H10 H 0.3073 0.4726 0.4133 0.042 Uiso 1 1 calc R . . C11 C 0.23579(10) 0.60707(9) 0.43527(7) 0.0266(2) Uani 1 1 d . . . H11 H 0.3010 0.6444 0.4464 0.032 Uiso 1 1 calc R . . C12 C 0.09625(9) 0.77804(9) 0.55077(6) 0.0210(2) Uani 1 1 d . . . C13 C 0.00707(10) 0.82778(12) 0.57102(7) 0.0315(3) Uani 1 1 d . . . H13 H -0.0390 0.8677 0.5394 0.038 Uiso 1 1 calc R . . C14 C -0.01441(11) 0.81880(15) 0.63796(7) 0.0420(4) Uani 1 1 d . . . H14 H -0.0754 0.8525 0.6519 0.050 Uiso 1 1 calc R . . C15 C 0.05279(12) 0.76094(14) 0.68425(7) 0.0382(3) Uani 1 1 d . . . H15 H 0.0374 0.7546 0.7297 0.046 Uiso 1 1 calc R . . C16 C 0.14289(11) 0.71204(11) 0.66432(6) 0.0296(3) Uani 1 1 d . . . H16 H 0.1894 0.6733 0.6963 0.035 Uiso 1 1 calc R . . C17 C 0.16480(10) 0.71993(9) 0.59762(6) 0.0231(2) Uani 1 1 d . . . H17 H 0.2259 0.6862 0.5839 0.028 Uiso 1 1 calc R . . S2 S 0.51955(3) 0.37443(2) 0.341662(15) 0.02479(7) Uani 1 1 d . . . P2 P 0.45125(2) 0.25489(2) 0.376793(13) 0.01530(6) Uani 1 1 d . . . N3 N 0.69168(7) 0.06861(7) 0.38985(5) 0.01708(16) Uani 1 1 d . . . N4 N 0.53174(7) 0.15407(7) 0.39631(4) 0.01522(16) Uani 1 1 d . . . H4N H 0.5272 0.1230 0.4352 0.018 Uiso 1 1 calc R . . C18 C 0.60581(8) 0.11519(8) 0.35563(5) 0.01516(18) Uani 1 1 d . . . C19 C 0.59007(9) 0.12296(8) 0.28472(5) 0.01932(19) Uani 1 1 d . . . H29 H 0.5275 0.1553 0.2618 0.023 Uiso 1 1 calc R . . C20 C 0.66857(10) 0.08204(9) 0.24900(6) 0.0235(2) Uani 1 1 d . . . H20 H 0.6610 0.0870 0.2009 0.028 Uiso 1 1 calc R . . C21 C 0.75820(9) 0.03379(9) 0.28392(6) 0.0241(2) Uani 1 1 d . . . H21 H 0.8129 0.0055 0.2603 0.029 Uiso 1 1 calc R . . C22 C 0.76583(9) 0.02800(9) 0.35382(6) 0.0216(2) Uani 1 1 d . . . H22 H 0.8263 -0.0063 0.3777 0.026 Uiso 1 1 calc R . . C23 C 0.33904(9) 0.20707(9) 0.31845(5) 0.0191(2) Uani 1 1 d . . . C24 C 0.28015(10) 0.27484(10) 0.27350(6) 0.0264(2) Uani 1 1 d . . . H24 H 0.2995 0.3452 0.2734 0.032 Uiso 1 1 calc R . . C25 C 0.19309(10) 0.23908(13) 0.22888(6) 0.0344(3) Uani 1 1 d . . . H25 H 0.1525 0.2853 0.1987 0.041 Uiso 1 1 calc R . . C26 C 0.16560(10) 0.13659(13) 0.22841(7) 0.0358(3) Uani 1 1 d . . . H26 H 0.1063 0.1125 0.1977 0.043 Uiso 1 1 calc R . . C27 C 0.22411(10) 0.06848(11) 0.27263(7) 0.0336(3) Uani 1 1 d . . . H27 H 0.2050 -0.0020 0.2720 0.040 Uiso 1 1 calc R . . C28 C 0.31097(10) 0.10373(9) 0.31798(6) 0.0258(2) Uani 1 1 d . . . H28 H 0.3509 0.0574 0.3485 0.031 Uiso 1 1 calc R . . C29 C 0.40094(8) 0.27906(8) 0.45679(5) 0.01693(18) Uani 1 1 d . . . C30 C 0.45687(10) 0.34990(9) 0.50092(6) 0.0219(2) Uani 1 1 d . . . H30 H 0.5193 0.3830 0.4886 0.026 Uiso 1 1 calc R . . C31 C 0.42121(12) 0.37195(10) 0.56276(6) 0.0300(3) Uani 1 1 d . . . H31 H 0.4598 0.4195 0.5930 0.036 Uiso 1 1 calc R . . C32 C 0.32907(12) 0.32448(11) 0.58034(7) 0.0327(3) Uani 1 1 d . . . H32 H 0.3044 0.3402 0.6225 0.039 Uiso 1 1 calc R . . C33 C 0.27292(11) 0.25446(11) 0.53686(7) 0.0302(3) Uani 1 1 d . . . H33 H 0.2101 0.2221 0.5493 0.036 Uiso 1 1 calc R . . C34 C 0.30849(9) 0.23132(9) 0.47483(6) 0.0228(2) Uani 1 1 d . . . H34 H 0.2700 0.1833 0.4450 0.027 Uiso 1 1 calc 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 0.02221(13) 0.02683(15) 0.02875(15) -0.00008(11) -0.00585(11) 0.00547(10) P1 0.01317(12) 0.01884(13) 0.01747(12) -0.00114(9) -0.00044(9) -0.00122(9) N1 0.0163(4) 0.0160(4) 0.0159(4) 0.0016(3) 0.0015(3) -0.0009(3) N2 0.0156(4) 0.0250(4) 0.0148(4) -0.0022(3) 0.0012(3) -0.0051(3) C1 0.0177(4) 0.0154(4) 0.0154(4) 0.0003(3) 0.0014(3) -0.0005(3) C2 0.0226(5) 0.0209(5) 0.0162(5) -0.0017(4) 0.0009(4) -0.0040(4) C3 0.0298(5) 0.0188(5) 0.0156(4) -0.0016(4) 0.0045(4) -0.0003(4) C4 0.0241(5) 0.0184(5) 0.0202(5) 0.0015(4) 0.0079(4) 0.0011(4) C5 0.0177(4) 0.0163(4) 0.0199(5) 0.0027(4) 0.0037(4) -0.0003(3) C6 0.0213(5) 0.0187(5) 0.0166(4) 0.0002(4) -0.0002(4) -0.0013(4) C7 0.0265(6) 0.0275(6) 0.0306(6) -0.0045(5) -0.0024(5) -0.0068(5) C8 0.0466(8) 0.0261(6) 0.0385(7) -0.0043(5) -0.0056(6) -0.0118(6) C9 0.0618(9) 0.0183(5) 0.0321(7) 0.0001(5) 0.0002(6) 0.0019(6) C10 0.0451(8) 0.0224(6) 0.0384(7) 0.0055(5) 0.0062(6) 0.0110(5) C11 0.0257(5) 0.0214(5) 0.0324(6) 0.0043(4) 0.0021(5) 0.0035(4) C12 0.0165(4) 0.0261(5) 0.0205(5) -0.0038(4) 0.0029(4) -0.0060(4) C13 0.0170(5) 0.0497(8) 0.0280(6) -0.0072(5) 0.0037(4) -0.0010(5) C14 0.0226(6) 0.0741(11) 0.0310(7) -0.0122(7) 0.0106(5) -0.0043(6) C15 0.0314(7) 0.0616(10) 0.0233(6) -0.0066(6) 0.0096(5) -0.0184(6) C16 0.0333(6) 0.0342(7) 0.0207(5) 0.0003(5) 0.0018(5) -0.0138(5) C17 0.0237(5) 0.0241(5) 0.0212(5) -0.0003(4) 0.0025(4) -0.0067(4) S2 0.03726(16) 0.01571(12) 0.02340(14) 0.00140(9) 0.01157(11) -0.00117(10) P2 0.01861(12) 0.01370(12) 0.01363(12) 0.00022(8) 0.00219(9) 0.00240(9) N3 0.0152(4) 0.0162(4) 0.0198(4) -0.0027(3) 0.0021(3) -0.0001(3) N4 0.0160(4) 0.0168(4) 0.0130(4) 0.0008(3) 0.0024(3) 0.0026(3) C18 0.0161(4) 0.0134(4) 0.0162(4) -0.0019(3) 0.0031(3) -0.0017(3) C19 0.0229(5) 0.0191(5) 0.0161(5) -0.0013(4) 0.0032(4) -0.0002(4) C20 0.0305(6) 0.0221(5) 0.0196(5) -0.0049(4) 0.0092(4) -0.0035(4) C21 0.0240(5) 0.0216(5) 0.0288(6) -0.0082(4) 0.0117(4) -0.0015(4) C22 0.0173(4) 0.0195(5) 0.0285(5) -0.0051(4) 0.0047(4) 0.0007(4) C23 0.0195(5) 0.0221(5) 0.0151(4) -0.0013(4) -0.0001(4) 0.0062(4) C24 0.0249(5) 0.0343(6) 0.0199(5) 0.0068(4) 0.0029(4) 0.0099(5) C25 0.0227(6) 0.0610(9) 0.0186(5) 0.0071(5) -0.0010(4) 0.0132(6) C26 0.0203(5) 0.0646(10) 0.0209(5) -0.0136(6) -0.0033(4) 0.0064(6) C27 0.0249(6) 0.0358(7) 0.0378(7) -0.0165(6) -0.0049(5) 0.0024(5) C28 0.0224(5) 0.0231(5) 0.0295(6) -0.0067(4) -0.0057(4) 0.0048(4) C29 0.0189(4) 0.0167(4) 0.0155(4) 0.0000(3) 0.0032(3) 0.0038(3) C30 0.0264(5) 0.0202(5) 0.0190(5) -0.0022(4) 0.0034(4) 0.0012(4) C31 0.0440(7) 0.0264(6) 0.0200(5) -0.0065(4) 0.0056(5) 0.0024(5) C32 0.0422(7) 0.0353(7) 0.0231(6) -0.0019(5) 0.0144(5) 0.0091(6) C33 0.0268(6) 0.0378(7) 0.0283(6) 0.0035(5) 0.0127(5) 0.0040(5) C34 0.0210(5) 0.0256(5) 0.0220(5) 0.0008(4) 0.0039(4) 0.0005(4) _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 S1 P1 1.9470(4) . ? P1 N2 1.6689(9) . ? P1 C12 1.8067(12) . ? P1 C6 1.8088(11) . ? N1 C1 1.3424(13) . ? N1 C5 1.3435(13) . ? N2 C1 1.3935(13) . ? N2 H2N 0.8800 . ? C1 C2 1.4029(14) . ? C2 C3 1.3845(15) . ? C2 H2 0.9500 . ? C3 C4 1.3920(16) . ? C3 H3 0.9500 . ? C4 C5 1.3842(15) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.3955(16) . ? C6 C11 1.3959(16) . ? C7 C8 1.3913(19) . ? C7 H7 0.9500 . ? C8 C9 1.388(2) . ? C8 H8 0.9500 . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.3930(18) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.3914(17) . ? C12 C17 1.4029(16) . ? C13 C14 1.3944(19) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.393(2) . ? C15 H15 0.9500 . ? C16 C17 1.3904(17) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? S2 P2 1.9497(4) . ? P2 N4 1.6706(9) . ? P2 C29 1.8094(11) . ? P2 C23 1.8096(11) . ? N3 C18 1.3385(13) . ? N3 C22 1.3486(13) . ? N4 C18 1.3986(12) . ? N4 H4N 0.8800 . ? C18 C19 1.4004(14) . ? C19 C20 1.3878(15) . ? C19 H29 0.9500 . ? C20 C21 1.3886(17) . ? C20 H20 0.9500 . ? C21 C22 1.3813(17) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.3936(17) . ? C23 C24 1.3966(15) . ? C24 C25 1.3912(19) . ? C24 H24 0.9500 . ? C25 C26 1.381(2) . ? C25 H25 0.9500 . ? C26 C27 1.389(2) . ? C26 H26 0.9500 . ? C27 C28 1.3950(16) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.3975(15) . ? C29 C34 1.3975(15) . ? C30 C31 1.3891(16) . ? C30 H30 0.9500 . ? C31 C32 1.389(2) . ? C31 H31 0.9500 . ? C32 C33 1.384(2) . ? C32 H32 0.9500 . ? C33 C34 1.3950(16) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? 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 P1 C12 99.87(5) . . ? N2 P1 C6 106.45(5) . . ? C12 P1 C6 104.03(5) . . ? N2 P1 S1 117.02(4) . . ? C12 P1 S1 115.23(4) . . ? C6 P1 S1 112.69(4) . . ? C1 N1 C5 118.15(9) . . ? C1 N2 P1 128.79(7) . . ? C1 N2 H2N 115.6 . . ? P1 N2 H2N 115.6 . . ? N1 C1 N2 113.77(9) . . ? N1 C1 C2 122.59(10) . . ? N2 C1 C2 123.61(9) . . ? C3 C2 C1 117.97(10) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 119.99(10) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 117.90(10) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 123.38(10) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C11 119.39(11) . . ? C7 C6 P1 117.73(9) . . ? C11 C6 P1 122.81(9) . . ? C8 C7 C6 119.93(13) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.27(13) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.17(13) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.89(13) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 120.31(12) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C17 120.16(11) . . ? C13 C12 P1 120.68(10) . . ? C17 C12 P1 119.16(9) . . ? C12 C13 C14 119.68(13) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.28(13) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.17(12) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.08(13) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 119.62(12) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? N4 P2 C29 101.52(4) . . ? N4 P2 C23 105.60(5) . . ? C29 P2 C23 107.18(5) . . ? N4 P2 S2 115.89(3) . . ? C29 P2 S2 113.04(4) . . ? C23 P2 S2 112.62(4) . . ? C18 N3 C22 117.90(9) . . ? C18 N4 P2 125.02(7) . . ? C18 N4 H4N 117.5 . . ? P2 N4 H4N 117.5 . . ? N3 C18 N4 114.61(9) . . ? N3 C18 C19 122.89(9) . . ? N4 C18 C19 122.49(9) . . ? C20 C19 C18 117.98(10) . . ? C20 C19 H29 121.0 . . ? C18 C19 H29 121.0 . . ? C19 C20 C21 119.68(10) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C22 C21 C20 118.27(10) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? N3 C22 C21 123.26(11) . . ? N3 C22 H22 118.4 . . ? C21 C22 H22 118.4 . . ? C28 C23 C24 119.88(11) . . ? C28 C23 P2 120.74(8) . . ? C24 C23 P2 119.38(9) . . ? C25 C24 C23 119.86(13) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 120.15(12) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 120.41(12) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C28 119.89(13) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C23 C28 C27 119.82(12) . . ? C23 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C30 C29 C34 119.75(10) . . ? C30 C29 P2 117.68(8) . . ? C34 C29 P2 122.56(8) . . ? C31 C30 C29 120.06(11) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 119.94(12) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C33 C32 C31 120.42(11) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.06(12) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C29 119.77(11) . . ? C33 C34 H34 120.1 . . ? C29 C34 H34 120.1 . . ? 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 C12 P1 N2 C1 173.79(10) . . . . ? C6 P1 N2 C1 65.86(11) . . . . ? S1 P1 N2 C1 -61.16(11) . . . . ? C5 N1 C1 N2 177.14(9) . . . . ? C5 N1 C1 C2 -0.76(15) . . . . ? P1 N2 C1 N1 179.81(8) . . . . ? P1 N2 C1 C2 -2.32(16) . . . . ? N1 C1 C2 C3 1.40(16) . . . . ? N2 C1 C2 C3 -176.29(10) . . . . ? C1 C2 C3 C4 -0.82(16) . . . . ? C2 C3 C4 C5 -0.30(16) . . . . ? C1 N1 C5 C4 -0.48(16) . . . . ? C3 C4 C5 N1 1.00(16) . . . . ? N2 P1 C6 C7 -179.80(9) . . . . ? C12 P1 C6 C7 75.26(10) . . . . ? S1 P1 C6 C7 -50.23(10) . . . . ? N2 P1 C6 C11 3.25(11) . . . . ? C12 P1 C6 C11 -101.70(10) . . . . ? S1 P1 C6 C11 132.81(9) . . . . ? C11 C6 C7 C8 -0.39(19) . . . . ? P1 C6 C7 C8 -177.45(11) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C7 C8 C9 C10 1.3(2) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 C6 -1.5(2) . . . . ? C7 C6 C11 C10 1.73(18) . . . . ? P1 C6 C11 C10 178.63(10) . . . . ? N2 P1 C12 C13 123.51(10) . . . . ? C6 P1 C12 C13 -126.62(10) . . . . ? S1 P1 C12 C13 -2.76(11) . . . . ? N2 P1 C12 C17 -56.61(10) . . . . ? C6 P1 C12 C17 53.25(10) . . . . ? S1 P1 C12 C17 177.11(8) . . . . ? C17 C12 C13 C14 -0.6(2) . . . . ? P1 C12 C13 C14 179.28(11) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? C13 C14 C15 C16 0.6(2) . . . . ? C14 C15 C16 C17 -0.9(2) . . . . ? C15 C16 C17 C12 0.53(18) . . . . ? C13 C12 C17 C16 0.22(17) . . . . ? P1 C12 C17 C16 -179.65(9) . . . . ? C29 P2 N4 C18 -168.18(8) . . . . ? C23 P2 N4 C18 80.11(9) . . . . ? S2 P2 N4 C18 -45.30(9) . . . . ? C22 N3 C18 N4 179.12(9) . . . . ? C22 N3 C18 C19 0.21(15) . . . . ? P2 N4 C18 N3 151.54(8) . . . . ? P2 N4 C18 C19 -29.55(14) . . . . ? N3 C18 C19 C20 -1.30(16) . . . . ? N4 C18 C19 C20 179.87(10) . . . . ? C18 C19 C20 C21 1.07(16) . . . . ? C19 C20 C21 C22 0.17(17) . . . . ? C18 N3 C22 C21 1.15(16) . . . . ? C20 C21 C22 N3 -1.34(17) . . . . ? N4 P2 C23 C28 24.06(11) . . . . ? C29 P2 C23 C28 -83.60(10) . . . . ? S2 P2 C23 C28 151.46(9) . . . . ? N4 P2 C23 C24 -155.97(9) . . . . ? C29 P2 C23 C24 96.37(10) . . . . ? S2 P2 C23 C24 -28.57(10) . . . . ? C28 C23 C24 C25 0.58(17) . . . . ? P2 C23 C24 C25 -179.39(9) . . . . ? C23 C24 C25 C26 -0.74(19) . . . . ? C24 C25 C26 C27 0.3(2) . . . . ? C25 C26 C27 C28 0.2(2) . . . . ? C24 C23 C28 C27 -0.03(18) . . . . ? P2 C23 C28 C27 179.94(10) . . . . ? C26 C27 C28 C23 -0.4(2) . . . . ? N4 P2 C29 C30 93.08(9) . . . . ? C23 P2 C29 C30 -156.41(8) . . . . ? S2 P2 C29 C30 -31.73(9) . . . . ? N4 P2 C29 C34 -88.11(10) . . . . ? C23 P2 C29 C34 22.40(11) . . . . ? S2 P2 C29 C34 147.09(8) . . . . ? C34 C29 C30 C31 0.63(17) . . . . ? P2 C29 C30 C31 179.48(9) . . . . ? C29 C30 C31 C32 -0.81(19) . . . . ? C30 C31 C32 C33 0.6(2) . . . . ? C31 C32 C33 C34 -0.2(2) . . . . ? C32 C33 C34 C29 0.00(19) . . . . ? C30 C29 C34 C33 -0.22(17) . . . . ? P2 C29 C34 C33 -179.01(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N3 0.88 2.08 2.9347(13) 162.3 3_666 N4 H4N N1 0.88 2.14 2.9261(12) 148.2 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.554 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.064 #===END # 1462 SPN-iPr at 100K data_1b-1462 _database_code_depnum_ccdc_archive 'CCDC 810364' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480_6b459 #_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1462 SPN-iPr at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 N2 P S' _chemical_formula_sum 'C11 H19 N2 P S' _chemical_formula_weight 242.31 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 16.0217(4) _cell_length_b 10.5230(2) _cell_length_c 16.4570(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.842(1) _cell_angle_gamma 90.00 _cell_volume 2625.91(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9518 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 30.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Prismatic crystals from acetone by evaporation. Bruker Smart APEX CCD 3-axis diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 28789 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7633 _reflns_number_gt 6948 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0445P)^2^+0.8597P] 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 7633 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 S1 S 0.228323(16) 0.46496(2) 0.266634(15) 0.01765(6) Uani 1 1 d . . . P1 P 0.294042(15) 0.32385(2) 0.238145(14) 0.01347(5) Uani 1 1 d . . . N1 N 0.43963(5) 0.19678(8) 0.18998(5) 0.01931(16) Uani 1 1 d . . . N2 N 0.37380(5) 0.38801(7) 0.20517(5) 0.01581(14) Uani 1 1 d . . . H2N H 0.3766 0.4715 0.2048 0.019 Uiso 1 1 calc R . . C1 C 0.43600(6) 0.32227(9) 0.17837(6) 0.01579(16) Uani 1 1 d . . . C2 C 0.49202(6) 0.38926(10) 0.14307(6) 0.02000(18) Uani 1 1 d . . . H2 H 0.4871 0.4787 0.1354 0.024 Uiso 1 1 calc R . . C3 C 0.55453(7) 0.32069(11) 0.11992(7) 0.0243(2) Uani 1 1 d . . . H3 H 0.5931 0.3626 0.0953 0.029 Uiso 1 1 calc R . . C4 C 0.56033(7) 0.18989(11) 0.13298(7) 0.0256(2) Uani 1 1 d . . . H4 H 0.6034 0.1411 0.1185 0.031 Uiso 1 1 calc R . . C5 C 0.50187(7) 0.13296(10) 0.16748(7) 0.02307(19) Uani 1 1 d . . . H5 H 0.5056 0.0436 0.1759 0.028 Uiso 1 1 calc R . . C6 C 0.22711(6) 0.22743(9) 0.14814(6) 0.01829(17) Uani 1 1 d . . . H6 H 0.2672 0.1655 0.1332 0.022 Uiso 1 1 calc R . . C7 C 0.18660(8) 0.31294(11) 0.06979(7) 0.0275(2) Uani 1 1 d . . . H7A H 0.1576 0.2601 0.0195 0.041 Uiso 1 1 calc R . . H7B H 0.2332 0.3635 0.0587 0.041 Uiso 1 1 calc R . . H7C H 0.1432 0.3699 0.0810 0.041 Uiso 1 1 calc R . . C8 C 0.15468(7) 0.15171(11) 0.16845(7) 0.0259(2) Uani 1 1 d . . . H8A H 0.1188 0.1070 0.1167 0.039 Uiso 1 1 calc R . . H8B H 0.1172 0.2099 0.1878 0.039 Uiso 1 1 calc R . . H8C H 0.1817 0.0898 0.2138 0.039 Uiso 1 1 calc R . . C9 C 0.34750(6) 0.22063(9) 0.33034(6) 0.01930(18) Uani 1 1 d . . . H9 H 0.3615 0.1377 0.3080 0.023 Uiso 1 1 calc R . . C10 C 0.43422(7) 0.27979(12) 0.38702(7) 0.0278(2) Uani 1 1 d . . . H10A H 0.4604 0.2256 0.4372 0.042 Uiso 1 1 calc R . . H10B H 0.4225 0.3643 0.4060 0.042 Uiso 1 1 calc R . . H10C H 0.4752 0.2874 0.3541 0.042 Uiso 1 1 calc R . . C11 C 0.28696(8) 0.19403(11) 0.38422(7) 0.0278(2) Uani 1 1 d . . . H11A H 0.3168 0.1363 0.4314 0.042 Uiso 1 1 calc R . . H11B H 0.2321 0.1548 0.3479 0.042 Uiso 1 1 calc R . . H11C H 0.2734 0.2741 0.4077 0.042 Uiso 1 1 calc R . . S2 S 0.321245(15) 0.61130(2) 0.049597(15) 0.01724(6) Uani 1 1 d . . . P2 P 0.222400(15) 0.72838(2) 0.035257(15) 0.01369(6) Uani 1 1 d . . . N3 N 0.06091(5) 0.84375(8) 0.06950(6) 0.02198(17) Uani 1 1 d . . . N4 N 0.16283(5) 0.67719(8) 0.09637(5) 0.01783(15) Uani 1 1 d . . . H4N H 0.1816 0.6070 0.1257 0.021 Uiso 1 1 calc R . . C12 C 0.08759(6) 0.73167(9) 0.10654(6) 0.01744(17) Uani 1 1 d . . . C13 C 0.04335(7) 0.66608(11) 0.15517(6) 0.02259(19) Uani 1 1 d . . . H13 H 0.0621 0.5841 0.1779 0.027 Uiso 1 1 calc R . . C14 C -0.02803(7) 0.72467(13) 0.16871(7) 0.0290(2) Uani 1 1 d . . . H14 H -0.0589 0.6834 0.2017 0.035 Uiso 1 1 calc R . . C15 C -0.05466(7) 0.84401(12) 0.13400(8) 0.0296(2) Uani 1 1 d . . . H15 H -0.1024 0.8871 0.1443 0.035 Uiso 1 1 calc R . . C16 C -0.00945(7) 0.89800(10) 0.08409(8) 0.0263(2) Uani 1 1 d . . . H16 H -0.0290 0.9782 0.0584 0.032 Uiso 1 1 calc R . . C17 C 0.25909(6) 0.88939(8) 0.07158(6) 0.01620(16) Uani 1 1 d . . . H17 H 0.2058 0.9431 0.0648 0.019 Uiso 1 1 calc R . . C18 C 0.31352(7) 0.88475(10) 0.16721(6) 0.02245(19) Uani 1 1 d . . . H18A H 0.3346 0.9703 0.1871 0.034 Uiso 1 1 calc R . . H18B H 0.3641 0.8280 0.1755 0.034 Uiso 1 1 calc R . . H18C H 0.2767 0.8530 0.2001 0.034 Uiso 1 1 calc R . . C19 C 0.31214(7) 0.94917(10) 0.01891(7) 0.02221(19) Uani 1 1 d . . . H19A H 0.3325 1.0338 0.0417 0.033 Uiso 1 1 calc R . . H19B H 0.2747 0.9565 -0.0412 0.033 Uiso 1 1 calc R . . H19C H 0.3632 0.8954 0.0225 0.033 Uiso 1 1 calc R . . C20 C 0.14719(6) 0.73410(9) -0.07623(6) 0.01842(17) Uani 1 1 d . . . H20 H 0.1159 0.8178 -0.0857 0.022 Uiso 1 1 calc R . . C21 C 0.07815(7) 0.62794(12) -0.09235(7) 0.0285(2) Uani 1 1 d . . . H21A H 0.0421 0.6276 -0.1531 0.043 Uiso 1 1 calc R . . H21B H 0.0403 0.6426 -0.0569 0.043 Uiso 1 1 calc R . . H21C H 0.1080 0.5458 -0.0773 0.043 Uiso 1 1 calc R . . C22 C 0.19814(7) 0.72190(10) -0.14043(6) 0.0237(2) Uani 1 1 d . . . H22A H 0.1568 0.7268 -0.1991 0.035 Uiso 1 1 calc R . . H22B H 0.2290 0.6401 -0.1321 0.035 Uiso 1 1 calc R . . H22C H 0.2412 0.7911 -0.1311 0.035 Uiso 1 1 calc 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 0.02178(11) 0.01610(10) 0.01740(11) 0.00029(7) 0.00959(8) 0.00350(8) P1 0.01481(10) 0.01272(10) 0.01371(10) 0.00031(7) 0.00577(8) 0.00017(7) N1 0.0184(4) 0.0191(4) 0.0211(4) 0.0002(3) 0.0073(3) 0.0027(3) N2 0.0162(3) 0.0136(3) 0.0195(4) 0.0008(3) 0.0084(3) -0.0001(3) C1 0.0133(4) 0.0196(4) 0.0140(4) 0.0001(3) 0.0038(3) 0.0009(3) C2 0.0162(4) 0.0257(5) 0.0184(4) 0.0034(3) 0.0059(3) -0.0001(3) C3 0.0172(4) 0.0374(6) 0.0198(4) 0.0022(4) 0.0081(4) 0.0007(4) C4 0.0186(4) 0.0370(6) 0.0217(5) -0.0037(4) 0.0074(4) 0.0065(4) C5 0.0209(4) 0.0241(5) 0.0234(5) -0.0020(4) 0.0060(4) 0.0059(4) C6 0.0194(4) 0.0177(4) 0.0191(4) -0.0045(3) 0.0080(3) -0.0034(3) C7 0.0302(5) 0.0315(5) 0.0170(4) -0.0008(4) 0.0022(4) -0.0100(4) C8 0.0255(5) 0.0248(5) 0.0299(5) -0.0045(4) 0.0126(4) -0.0095(4) C9 0.0219(4) 0.0186(4) 0.0182(4) 0.0048(3) 0.0076(3) 0.0032(3) C10 0.0250(5) 0.0359(6) 0.0186(4) 0.0052(4) 0.0016(4) 0.0004(4) C11 0.0310(5) 0.0304(5) 0.0259(5) 0.0111(4) 0.0144(4) 0.0035(4) S2 0.01766(11) 0.01671(10) 0.01890(11) 0.00351(8) 0.00803(8) 0.00449(7) P2 0.01392(10) 0.01284(10) 0.01506(10) 0.00156(7) 0.00572(8) 0.00099(7) N3 0.0167(4) 0.0195(4) 0.0316(5) -0.0026(3) 0.0103(3) 0.0006(3) N4 0.0186(4) 0.0162(3) 0.0220(4) 0.0043(3) 0.0110(3) 0.0021(3) C12 0.0156(4) 0.0200(4) 0.0181(4) -0.0035(3) 0.0074(3) -0.0024(3) C13 0.0179(4) 0.0324(5) 0.0184(4) 0.0001(4) 0.0070(3) -0.0051(4) C14 0.0180(5) 0.0507(7) 0.0207(5) -0.0059(4) 0.0095(4) -0.0069(4) C15 0.0159(4) 0.0435(6) 0.0308(5) -0.0176(5) 0.0097(4) -0.0027(4) C16 0.0167(4) 0.0247(5) 0.0376(6) -0.0100(4) 0.0087(4) 0.0002(4) C17 0.0178(4) 0.0139(4) 0.0173(4) 0.0000(3) 0.0062(3) 0.0000(3) C18 0.0281(5) 0.0218(4) 0.0164(4) -0.0016(3) 0.0056(4) -0.0019(4) C19 0.0268(5) 0.0197(4) 0.0215(4) 0.0003(3) 0.0097(4) -0.0063(4) C20 0.0170(4) 0.0184(4) 0.0181(4) 0.0009(3) 0.0032(3) 0.0010(3) C21 0.0233(5) 0.0353(6) 0.0257(5) -0.0049(4) 0.0063(4) -0.0102(4) C22 0.0252(5) 0.0289(5) 0.0165(4) 0.0016(4) 0.0062(4) -0.0014(4) _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 S1 P1 1.9627(3) . ? P1 N2 1.6826(8) . ? P1 C6 1.8297(10) . ? P1 C9 1.8375(10) . ? N1 C1 1.3329(12) . ? N1 C5 1.3494(12) . ? N2 C1 1.3963(11) . ? N2 H2N 0.8800 . ? C1 C2 1.4061(13) . ? C2 C3 1.3840(14) . ? C2 H2 0.9500 . ? C3 C4 1.3916(16) . ? C3 H3 0.9500 . ? C4 C5 1.3792(15) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C8 1.5310(13) . ? C6 C7 1.5339(14) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5332(15) . ? C9 C11 1.5365(14) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? S2 P2 1.9596(3) . ? P2 N4 1.6830(8) . ? P2 C17 1.8294(9) . ? P2 C20 1.8423(10) . ? N3 C12 1.3331(13) . ? N3 C16 1.3525(13) . ? N4 C12 1.3928(12) . ? N4 H4N 0.8800 . ? C12 C13 1.4091(13) . ? C13 C14 1.3792(15) . ? C13 H13 0.9500 . ? C14 C15 1.3885(19) . ? C14 H14 0.9500 . ? C15 C16 1.3806(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C19 1.5315(13) . ? C17 C18 1.5340(13) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.5338(14) . ? C20 C22 1.5350(14) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 P1 C6 105.60(4) . . ? N2 P1 C9 107.67(4) . . ? C6 P1 C9 109.62(5) . . ? N2 P1 S1 107.18(3) . . ? C6 P1 S1 113.18(3) . . ? C9 P1 S1 113.14(3) . . ? C1 N1 C5 117.12(9) . . ? C1 N2 P1 126.65(6) . . ? C1 N2 H2N 116.7 . . ? P1 N2 H2N 116.7 . . ? N1 C1 N2 116.63(8) . . ? N1 C1 C2 123.48(9) . . ? N2 C1 C2 119.87(8) . . ? C3 C2 C1 117.88(10) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 119.43(10) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.22(9) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.85(10) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C8 C6 C7 110.12(9) . . ? C8 C6 P1 113.53(7) . . ? C7 C6 P1 109.48(7) . . ? C8 C6 H6 107.8 . . ? C7 C6 H6 107.8 . . ? P1 C6 H6 107.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 109.87(9) . . ? C10 C9 P1 110.57(7) . . ? C11 C9 P1 111.80(7) . . ? C10 C9 H9 108.2 . . ? C11 C9 H9 108.2 . . ? P1 C9 H9 108.2 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 P2 C17 106.59(4) . . ? N4 P2 C20 106.91(4) . . ? C17 P2 C20 109.45(4) . . ? N4 P2 S2 108.60(3) . . ? C17 P2 S2 112.40(3) . . ? C20 P2 S2 112.56(3) . . ? C12 N3 C16 117.05(9) . . ? C12 N4 P2 128.31(7) . . ? C12 N4 H4N 115.8 . . ? P2 N4 H4N 115.8 . . ? N3 C12 N4 118.12(8) . . ? N3 C12 C13 123.17(9) . . ? N4 C12 C13 118.70(9) . . ? C14 C13 C12 117.92(10) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C13 C14 C15 119.90(10) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 117.80(10) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? N3 C16 C15 124.02(11) . . ? N3 C16 H16 118.0 . . ? C15 C16 H16 118.0 . . ? C19 C17 C18 110.99(8) . . ? C19 C17 P2 111.96(6) . . ? C18 C17 P2 108.79(6) . . ? C19 C17 H17 108.3 . . ? C18 C17 H17 108.3 . . ? P2 C17 H17 108.3 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 109.53(8) . . ? C21 C20 P2 110.58(7) . . ? C22 C20 P2 111.13(7) . . ? C21 C20 H20 108.5 . . ? C22 C20 H20 108.5 . . ? P2 C20 H20 108.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 P1 N2 C1 -58.86(9) . . . . ? C9 P1 N2 C1 58.18(9) . . . . ? S1 P1 N2 C1 -179.80(7) . . . . ? C5 N1 C1 N2 -177.42(8) . . . . ? C5 N1 C1 C2 1.12(14) . . . . ? P1 N2 C1 N1 -8.89(12) . . . . ? P1 N2 C1 C2 172.52(7) . . . . ? N1 C1 C2 C3 -0.51(14) . . . . ? N2 C1 C2 C3 177.98(9) . . . . ? C1 C2 C3 C4 -0.64(15) . . . . ? C2 C3 C4 C5 1.12(15) . . . . ? C1 N1 C5 C4 -0.60(15) . . . . ? C3 C4 C5 N1 -0.51(16) . . . . ? N2 P1 C6 C8 175.25(7) . . . . ? C9 P1 C6 C8 59.53(8) . . . . ? S1 P1 C6 C8 -67.80(8) . . . . ? N2 P1 C6 C7 -61.24(8) . . . . ? C9 P1 C6 C7 -176.96(7) . . . . ? S1 P1 C6 C7 55.71(8) . . . . ? N2 P1 C9 C10 37.60(8) . . . . ? C6 P1 C9 C10 152.01(7) . . . . ? S1 P1 C9 C10 -80.64(7) . . . . ? N2 P1 C9 C11 160.36(7) . . . . ? C6 P1 C9 C11 -85.23(8) . . . . ? S1 P1 C9 C11 42.12(8) . . . . ? C17 P2 N4 C12 58.03(9) . . . . ? C20 P2 N4 C12 -58.95(9) . . . . ? S2 P2 N4 C12 179.35(8) . . . . ? C16 N3 C12 N4 -176.52(9) . . . . ? C16 N3 C12 C13 3.54(15) . . . . ? P2 N4 C12 N3 -5.71(13) . . . . ? P2 N4 C12 C13 174.23(7) . . . . ? N3 C12 C13 C14 -3.71(15) . . . . ? N4 C12 C13 C14 176.35(9) . . . . ? C12 C13 C14 C15 0.67(15) . . . . ? C13 C14 C15 C16 2.16(16) . . . . ? C12 N3 C16 C15 -0.41(16) . . . . ? C14 C15 C16 N3 -2.40(17) . . . . ? N4 P2 C17 C19 -178.24(7) . . . . ? C20 P2 C17 C19 -62.96(8) . . . . ? S2 P2 C17 C19 62.89(7) . . . . ? N4 P2 C17 C18 58.73(7) . . . . ? C20 P2 C17 C18 174.01(7) . . . . ? S2 P2 C17 C18 -60.14(7) . . . . ? N4 P2 C20 C21 -33.31(8) . . . . ? C17 P2 C20 C21 -148.38(7) . . . . ? S2 P2 C20 C21 85.86(7) . . . . ? N4 P2 C20 C22 -155.18(7) . . . . ? C17 P2 C20 C22 89.75(7) . . . . ? S2 P2 C20 C22 -36.01(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N S2 0.88 2.83 3.3753(8) 121.6 . N4 H4N S1 0.88 2.66 3.4700(8) 154.2 . C2 H2 S2 0.95 2.93 3.5487(10) 124.0 . C13 H13 S1 0.95 2.88 3.6215(11) 135.9 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.498 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.057 #===END # 1457 SePN-Ph at 100K data_2a-1457 _database_code_depnum_ccdc_archive 'CCDC 810365' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480_6b459_ #7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1457 SePN-Ph at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N2 P Se' _chemical_formula_sum 'C17 H15 N2 P Se' _chemical_formula_weight 357.24 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.5485(10) _cell_length_b 13.0789(11) _cell_length_c 20.0218(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.078(1) _cell_angle_gamma 90.00 _cell_volume 3260.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5840 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 29.94 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 2.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Bruker Smart APEX CCD 3-axis diffractometer. The structure contains two independent molecules which differ significantly in conformation. The compound is isostructural with the corresponding sulfur-compound (1a-1463). ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 36143 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9478 _reflns_number_gt 7638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0490P)^2^+1.3633P] 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 9478 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Se1 Se 0.022418(15) 0.873049(15) 0.401763(10) 0.02501(6) Uani 1 1 d . . . P1 P 0.12993(3) 0.78542(3) 0.46713(2) 0.01533(9) Uani 1 1 d . . . N1 N 0.42169(12) 0.88677(11) 0.46059(7) 0.0149(3) Uani 1 1 d . . . N2 N 0.25604(11) 0.82827(12) 0.48068(7) 0.0175(3) Uani 1 1 d . . . H2N H 0.2805 0.8416 0.5229 0.021 Uiso 1 1 calc R . . C1 C 0.32774(13) 0.84574(13) 0.43397(9) 0.0154(3) Uani 1 1 d . . . C2 C 0.30677(15) 0.81992(14) 0.36559(9) 0.0195(3) Uani 1 1 d . . . H2 H 0.2393 0.7922 0.3476 0.023 Uiso 1 1 calc R . . C3 C 0.38659(15) 0.83581(14) 0.32522(9) 0.0203(4) Uani 1 1 d . . . H3 H 0.3747 0.8185 0.2788 0.024 Uiso 1 1 calc R . . C4 C 0.48478(15) 0.87723(13) 0.35242(9) 0.0197(3) Uani 1 1 d . . . H4 H 0.5409 0.8881 0.3254 0.024 Uiso 1 1 calc R . . C5 C 0.49759(14) 0.90209(13) 0.42033(9) 0.0173(3) Uani 1 1 d . . . H5 H 0.5637 0.9315 0.4392 0.021 Uiso 1 1 calc R . . C6 C 0.13805(14) 0.65393(13) 0.43998(9) 0.0174(3) Uani 1 1 d . . . C7 C 0.04248(17) 0.60011(16) 0.42370(11) 0.0278(4) Uani 1 1 d . . . H7 H -0.0245 0.6333 0.4252 0.033 Uiso 1 1 calc R . . C8 C 0.0455(2) 0.49776(17) 0.40526(12) 0.0372(5) Uani 1 1 d . . . H8 H -0.0196 0.4606 0.3952 0.045 Uiso 1 1 calc R . . C9 C 0.1428(2) 0.44972(17) 0.40148(12) 0.0376(5) Uani 1 1 d . . . H9 H 0.1442 0.3802 0.3879 0.045 Uiso 1 1 calc R . . C10 C 0.2376(2) 0.50255(16) 0.41743(12) 0.0348(5) Uani 1 1 d . . . H10 H 0.3043 0.4695 0.4145 0.042 Uiso 1 1 calc R . . C11 C 0.23589(16) 0.60403(15) 0.43778(11) 0.0260(4) Uani 1 1 d . . . H11 H 0.3014 0.6395 0.4502 0.031 Uiso 1 1 calc R . . C12 C 0.09957(14) 0.77600(14) 0.55294(9) 0.0184(3) Uani 1 1 d . . . C13 C 0.01069(15) 0.82570(17) 0.57314(10) 0.0262(4) Uani 1 1 d . . . H13 H -0.0347 0.8657 0.5418 0.031 Uiso 1 1 calc R . . C14 C -0.01137(17) 0.8167(2) 0.63925(11) 0.0338(5) Uani 1 1 d . . . H14 H -0.0721 0.8502 0.6531 0.041 Uiso 1 1 calc R . . C15 C 0.05511(17) 0.75870(19) 0.68503(11) 0.0323(5) Uani 1 1 d . . . H15 H 0.0394 0.7522 0.7301 0.039 Uiso 1 1 calc R . . C16 C 0.14471(17) 0.70998(16) 0.66533(10) 0.0266(4) Uani 1 1 d . . . H16 H 0.1907 0.6713 0.6971 0.032 Uiso 1 1 calc R . . C17 C 0.16687(15) 0.71798(14) 0.59932(9) 0.0210(4) Uani 1 1 d . . . H17 H 0.2276 0.6841 0.5857 0.025 Uiso 1 1 calc R . . Se2 Se 0.520625(17) 0.382521(14) 0.340251(10) 0.02400(6) Uani 1 1 d . . . P2 P 0.44763(4) 0.25240(3) 0.37640(2) 0.01429(9) Uani 1 1 d . . . N3 N 0.68914(11) 0.06953(11) 0.38881(7) 0.0159(3) Uani 1 1 d . . . N4 N 0.52869(11) 0.15255(11) 0.39506(7) 0.0140(3) Uani 1 1 d . . . H4N H 0.5242 0.1211 0.4334 0.017 Uiso 1 1 calc R . . C18 C 0.60318(13) 0.11481(12) 0.35476(9) 0.0139(3) Uani 1 1 d . . . C19 C 0.58856(15) 0.12268(13) 0.28454(9) 0.0181(3) Uani 1 1 d . . . H29 H 0.5265 0.1548 0.2618 0.022 Uiso 1 1 calc R . . C20 C 0.66704(15) 0.08242(15) 0.24911(10) 0.0217(4) Uani 1 1 d . . . H20 H 0.6599 0.0871 0.2014 0.026 Uiso 1 1 calc R . . C21 C 0.75618(15) 0.03519(15) 0.28407(10) 0.0233(4) Uani 1 1 d . . . H21 H 0.8109 0.0071 0.2608 0.028 Uiso 1 1 calc R . . C22 C 0.76351(14) 0.02994(14) 0.35304(10) 0.0211(4) Uani 1 1 d . . . H22 H 0.8241 -0.0033 0.3767 0.025 Uiso 1 1 calc R . . C23 C 0.33681(14) 0.20468(14) 0.31794(9) 0.0184(3) Uani 1 1 d . . . C24 C 0.27777(16) 0.27152(17) 0.27371(10) 0.0263(4) Uani 1 1 d . . . H24 H 0.2963 0.3419 0.2734 0.032 Uiso 1 1 calc R . . C25 C 0.19160(16) 0.2349(2) 0.23004(10) 0.0339(5) Uani 1 1 d . . . H25 H 0.1505 0.2806 0.2003 0.041 Uiso 1 1 calc R . . C26 C 0.16534(17) 0.1324(2) 0.22961(11) 0.0355(5) Uani 1 1 d . . . H26 H 0.1067 0.1078 0.1994 0.043 Uiso 1 1 calc R . . C27 C 0.22439(17) 0.06498(19) 0.27325(11) 0.0336(5) Uani 1 1 d . . . H27 H 0.2061 -0.0055 0.2729 0.040 Uiso 1 1 calc R . . C28 C 0.31042(15) 0.10094(15) 0.31751(11) 0.0248(4) Uani 1 1 d . . . H28 H 0.3511 0.0550 0.3474 0.030 Uiso 1 1 calc R . . C29 C 0.39610(14) 0.27459(13) 0.45565(9) 0.0160(3) Uani 1 1 d . . . C30 C 0.45095(16) 0.34365(15) 0.50082(10) 0.0228(4) Uani 1 1 d . . . H30 H 0.5136 0.3770 0.4895 0.027 Uiso 1 1 calc R . . C31 C 0.4142(2) 0.36359(17) 0.56202(11) 0.0318(5) Uani 1 1 d . . . H31 H 0.4521 0.4098 0.5929 0.038 Uiso 1 1 calc R . . C32 C 0.3220(2) 0.31576(19) 0.57797(11) 0.0355(5) Uani 1 1 d . . . H32 H 0.2966 0.3298 0.6198 0.043 Uiso 1 1 calc R . . C33 C 0.26665(17) 0.24789(18) 0.53362(11) 0.0326(5) Uani 1 1 d . . . H33 H 0.2035 0.2156 0.5449 0.039 Uiso 1 1 calc R . . C34 C 0.30354(15) 0.22686(15) 0.47229(10) 0.0230(4) Uani 1 1 d . . . H34 H 0.2657 0.1800 0.4418 0.028 Uiso 1 1 calc 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 Se1 0.02120(10) 0.02499(10) 0.02700(11) 0.00116(8) -0.00435(7) 0.00523(7) P1 0.01312(19) 0.0157(2) 0.0164(2) -0.00097(16) -0.00109(15) -0.00115(15) N1 0.0167(7) 0.0141(7) 0.0135(7) 0.0005(5) 0.0005(5) -0.0010(5) N2 0.0156(7) 0.0233(8) 0.0132(7) -0.0023(6) 0.0004(5) -0.0060(6) C1 0.0172(8) 0.0141(7) 0.0146(8) 0.0006(6) 0.0010(6) -0.0015(6) C2 0.0227(8) 0.0187(8) 0.0164(8) -0.0022(7) -0.0004(7) -0.0035(7) C3 0.0291(9) 0.0175(8) 0.0143(8) -0.0024(6) 0.0028(7) 0.0001(7) C4 0.0239(9) 0.0175(8) 0.0188(9) 0.0026(7) 0.0066(7) -0.0001(7) C5 0.0181(8) 0.0143(7) 0.0196(9) 0.0020(6) 0.0019(6) -0.0002(6) C6 0.0200(8) 0.0158(8) 0.0157(8) 0.0003(6) -0.0008(6) -0.0013(6) C7 0.0241(9) 0.0260(10) 0.0316(11) -0.0045(8) -0.0031(8) -0.0053(8) C8 0.0445(13) 0.0237(10) 0.0406(13) -0.0052(9) -0.0068(10) -0.0108(9) C9 0.0639(16) 0.0170(9) 0.0301(11) -0.0018(8) -0.0017(11) 0.0018(10) C10 0.0448(13) 0.0202(10) 0.0400(13) 0.0038(9) 0.0070(10) 0.0119(9) C11 0.0242(9) 0.0202(9) 0.0331(11) 0.0039(8) 0.0015(8) 0.0032(7) C12 0.0160(8) 0.0207(8) 0.0182(8) -0.0024(7) 0.0007(6) -0.0059(6) C13 0.0173(8) 0.0363(11) 0.0250(10) -0.0035(8) 0.0027(7) -0.0009(8) C14 0.0204(9) 0.0530(14) 0.0292(11) -0.0081(10) 0.0078(8) -0.0029(9) C15 0.0285(10) 0.0470(13) 0.0227(10) -0.0045(9) 0.0086(8) -0.0140(9) C16 0.0300(10) 0.0284(10) 0.0210(9) 0.0016(8) 0.0007(8) -0.0098(8) C17 0.0212(8) 0.0203(9) 0.0214(9) 0.0007(7) 0.0013(7) -0.0044(7) Se2 0.03514(11) 0.01439(9) 0.02443(11) 0.00187(7) 0.01145(8) 0.00000(7) P2 0.0175(2) 0.01268(19) 0.0128(2) 0.00020(15) 0.00207(15) 0.00264(15) N3 0.0145(6) 0.0141(7) 0.0188(7) -0.0021(5) 0.0014(5) -0.0002(5) N4 0.0149(6) 0.0147(6) 0.0126(7) 0.0011(5) 0.0028(5) 0.0028(5) C18 0.0146(7) 0.0111(7) 0.0163(8) -0.0021(6) 0.0037(6) -0.0026(6) C19 0.0213(8) 0.0176(8) 0.0155(8) -0.0014(6) 0.0025(6) 0.0000(6) C20 0.0266(9) 0.0213(9) 0.0186(9) -0.0061(7) 0.0087(7) -0.0050(7) C21 0.0220(9) 0.0204(9) 0.0294(10) -0.0091(7) 0.0116(8) -0.0031(7) C22 0.0142(8) 0.0187(8) 0.0305(10) -0.0053(7) 0.0039(7) 0.0011(6) C23 0.0176(8) 0.0239(9) 0.0134(8) -0.0017(7) 0.0000(6) 0.0062(7) C24 0.0237(9) 0.0362(11) 0.0191(9) 0.0066(8) 0.0034(7) 0.0108(8) C25 0.0218(9) 0.0615(15) 0.0174(9) 0.0071(10) -0.0016(7) 0.0145(10) C26 0.0194(9) 0.0666(17) 0.0191(10) -0.0138(10) -0.0039(7) 0.0040(10) C27 0.0264(10) 0.0362(12) 0.0359(12) -0.0168(10) -0.0051(9) 0.0022(9) C28 0.0216(9) 0.0235(9) 0.0274(10) -0.0065(8) -0.0047(7) 0.0059(7) C29 0.0191(8) 0.0151(8) 0.0141(8) -0.0001(6) 0.0028(6) 0.0057(6) C30 0.0280(9) 0.0198(9) 0.0204(9) -0.0029(7) 0.0023(7) 0.0017(7) C31 0.0498(13) 0.0275(10) 0.0185(10) -0.0080(8) 0.0058(9) 0.0038(9) C32 0.0445(13) 0.0417(13) 0.0228(10) -0.0027(9) 0.0139(9) 0.0135(10) C33 0.0278(10) 0.0436(13) 0.0289(11) 0.0063(9) 0.0138(9) 0.0073(9) C34 0.0213(9) 0.0277(10) 0.0201(9) 0.0008(7) 0.0036(7) 0.0003(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 Se1 P1 2.1004(5) . ? P1 N2 1.6692(15) . ? P1 C12 1.8093(19) . ? P1 C6 1.8103(18) . ? N1 C5 1.337(2) . ? N1 C1 1.344(2) . ? N2 C1 1.394(2) . ? N2 H2N 0.8800 . ? C1 C2 1.403(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.394(3) . ? C6 C11 1.396(3) . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.383(4) . ? C8 H8 0.9500 . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.393(3) . ? C12 C17 1.399(3) . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? Se2 P2 2.1030(5) . ? P2 N4 1.6692(14) . ? P2 C29 1.8093(18) . ? P2 C23 1.8143(18) . ? N3 C18 1.341(2) . ? N3 C22 1.348(2) . ? N4 C18 1.398(2) . ? N4 H4N 0.8800 . ? C18 C19 1.399(2) . ? C19 C20 1.387(3) . ? C19 H29 0.9500 . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 C22 1.374(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.391(3) . ? C23 C28 1.396(3) . ? C24 C25 1.389(3) . ? C24 H24 0.9500 . ? C25 C26 1.380(4) . ? C25 H25 0.9500 . ? C26 C27 1.389(3) . ? C26 H26 0.9500 . ? C27 C28 1.391(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.395(3) . ? C29 C30 1.398(3) . ? C30 C31 1.386(3) . ? C30 H30 0.9500 . ? C31 C32 1.388(3) . ? C31 H31 0.9500 . ? C32 C33 1.381(3) . ? C32 H32 0.9500 . ? C33 C34 1.392(3) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? 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 P1 C12 100.07(8) . . ? N2 P1 C6 106.29(8) . . ? C12 P1 C6 104.28(8) . . ? N2 P1 Se1 116.19(6) . . ? C12 P1 Se1 115.76(6) . . ? C6 P1 Se1 112.76(6) . . ? C5 N1 C1 118.43(15) . . ? C1 N2 P1 128.56(12) . . ? C1 N2 H2N 115.7 . . ? P1 N2 H2N 115.7 . . ? N1 C1 N2 113.98(15) . . ? N1 C1 C2 122.20(16) . . ? N2 C1 C2 123.78(15) . . ? C3 C2 C1 118.26(16) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.05(17) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 117.64(17) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 123.41(16) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C11 119.42(18) . . ? C7 C6 P1 118.11(15) . . ? C11 C6 P1 122.40(14) . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 120.1(2) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C13 C12 C17 119.98(18) . . ? C13 C12 P1 120.90(15) . . ? C17 C12 P1 119.12(14) . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 119.84(19) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? N4 P2 C29 101.71(7) . . ? N4 P2 C23 105.83(8) . . ? C29 P2 C23 107.02(8) . . ? N4 P2 Se2 115.53(5) . . ? C29 P2 Se2 112.95(6) . . ? C23 P2 Se2 112.83(6) . . ? C18 N3 C22 117.77(15) . . ? C18 N4 P2 125.41(12) . . ? C18 N4 H4N 117.3 . . ? P2 N4 H4N 117.3 . . ? N3 C18 N4 114.57(15) . . ? N3 C18 C19 122.75(16) . . ? N4 C18 C19 122.68(15) . . ? C20 C19 C18 118.22(17) . . ? C20 C19 H29 120.9 . . ? C18 C19 H29 120.9 . . ? C19 C20 C21 119.31(17) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 118.59(17) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? N3 C22 C21 123.35(17) . . ? N3 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? C24 C23 C28 119.95(18) . . ? C24 C23 P2 120.01(16) . . ? C28 C23 P2 120.03(13) . . ? C25 C24 C23 119.7(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 120.4(2) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 120.25(19) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C28 119.9(2) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C23 119.81(19) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? C34 C29 C30 119.53(17) . . ? C34 C29 P2 122.40(14) . . ? C30 C29 P2 118.06(14) . . ? C31 C30 C29 120.18(19) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 119.8(2) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C33 C32 C31 120.6(2) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 119.9(2) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C29 119.97(19) . . ? C33 C34 H34 120.0 . . ? C29 C34 H34 120.0 . . ? 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 C12 P1 N2 C1 175.88(16) . . . . ? C6 P1 N2 C1 67.65(17) . . . . ? Se1 P1 N2 C1 -58.72(17) . . . . ? C5 N1 C1 N2 177.04(15) . . . . ? C5 N1 C1 C2 -0.8(2) . . . . ? P1 N2 C1 N1 175.98(13) . . . . ? P1 N2 C1 C2 -6.2(3) . . . . ? N1 C1 C2 C3 1.2(3) . . . . ? N2 C1 C2 C3 -176.38(17) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C1 N1 C5 C4 -0.4(3) . . . . ? C3 C4 C5 N1 1.1(3) . . . . ? N2 P1 C6 C7 -178.62(15) . . . . ? C12 P1 C6 C7 76.17(17) . . . . ? Se1 P1 C6 C7 -50.21(17) . . . . ? N2 P1 C6 C11 4.31(18) . . . . ? C12 P1 C6 C11 -100.91(17) . . . . ? Se1 P1 C6 C11 132.71(15) . . . . ? C11 C6 C7 C8 -0.2(3) . . . . ? P1 C6 C7 C8 -177.40(18) . . . . ? C6 C7 C8 C9 -1.5(4) . . . . ? C7 C8 C9 C10 1.4(4) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C9 C10 C11 C6 -2.2(3) . . . . ? C7 C6 C11 C10 2.1(3) . . . . ? P1 C6 C11 C10 179.10(17) . . . . ? N2 P1 C12 C13 124.88(16) . . . . ? C6 P1 C12 C13 -125.29(16) . . . . ? Se1 P1 C12 C13 -0.81(18) . . . . ? N2 P1 C12 C17 -55.00(16) . . . . ? C6 P1 C12 C17 54.83(16) . . . . ? Se1 P1 C12 C17 179.31(12) . . . . ? C17 C12 C13 C14 -0.6(3) . . . . ? P1 C12 C13 C14 179.53(16) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C12 0.7(3) . . . . ? C13 C12 C17 C16 0.1(3) . . . . ? P1 C12 C17 C16 180.00(14) . . . . ? C29 P2 N4 C18 -168.46(14) . . . . ? C23 P2 N4 C18 79.86(15) . . . . ? Se2 P2 N4 C18 -45.76(15) . . . . ? C22 N3 C18 N4 179.00(15) . . . . ? C22 N3 C18 C19 -0.3(2) . . . . ? P2 N4 C18 N3 151.01(12) . . . . ? P2 N4 C18 C19 -29.7(2) . . . . ? N3 C18 C19 C20 -0.5(3) . . . . ? N4 C18 C19 C20 -179.75(16) . . . . ? C18 C19 C20 C21 0.6(3) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? C18 N3 C22 C21 1.0(3) . . . . ? C20 C21 C22 N3 -0.9(3) . . . . ? N4 P2 C23 C24 -155.77(15) . . . . ? C29 P2 C23 C24 96.33(16) . . . . ? Se2 P2 C23 C24 -28.51(17) . . . . ? N4 P2 C23 C28 24.52(18) . . . . ? C29 P2 C23 C28 -83.38(17) . . . . ? Se2 P2 C23 C28 151.78(14) . . . . ? C28 C23 C24 C25 1.1(3) . . . . ? P2 C23 C24 C25 -178.66(15) . . . . ? C23 C24 C25 C26 -1.0(3) . . . . ? C24 C25 C26 C27 0.5(3) . . . . ? C25 C26 C27 C28 -0.1(3) . . . . ? C26 C27 C28 C23 0.1(3) . . . . ? C24 C23 C28 C27 -0.6(3) . . . . ? P2 C23 C28 C27 179.08(16) . . . . ? N4 P2 C29 C34 -89.31(16) . . . . ? C23 P2 C29 C34 21.47(17) . . . . ? Se2 P2 C29 C34 146.24(13) . . . . ? N4 P2 C29 C30 91.81(15) . . . . ? C23 P2 C29 C30 -157.41(14) . . . . ? Se2 P2 C29 C30 -32.64(15) . . . . ? C34 C29 C30 C31 0.7(3) . . . . ? P2 C29 C30 C31 179.65(16) . . . . ? C29 C30 C31 C32 -0.8(3) . . . . ? C30 C31 C32 C33 0.4(3) . . . . ? C31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C29 -0.2(3) . . . . ? C30 C29 C34 C33 -0.2(3) . . . . ? P2 C29 C34 C33 -179.08(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N3 0.88 2.11 2.940(2) 156.7 3_666 N4 H4N N1 0.88 2.15 2.926(2) 146.9 3_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.980 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.089 #===END # 1275 SePN-iPr at 100K data_2b-1475 _database_code_depnum_ccdc_archive 'CCDC 810366' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480_ #6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1275 SePN-iPr at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 N2 P Se' _chemical_formula_sum 'C11 H19 N2 P Se' _chemical_formula_weight 289.21 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3823(4) _cell_length_b 10.6502(5) _cell_length_c 12.1081(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.1470(10) _cell_angle_gamma 90.00 _cell_volume 1338.57(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5567 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 30.00 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from dichloromethane by evaporation. Bruker Smart APEX CCD 3-axis diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 15945 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3894 _reflns_number_gt 3687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0308P)^2^+0.3792P] 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 3894 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0515 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _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 Se1 Se 0.667025(10) 0.046521(10) 0.371763(9) 0.01910(4) Uani 1 1 d . . . P1 P 0.51628(2) 0.17288(2) 0.33154(2) 0.01378(6) Uani 1 1 d . . . N1 N 0.23571(9) 0.25337(9) 0.30632(7) 0.01887(17) Uani 1 1 d . . . N2 N 0.37974(8) 0.09782(8) 0.36409(7) 0.01601(16) Uani 1 1 d . . . H2N H 0.3893 0.0231 0.3942 0.019 Uiso 1 1 calc R . . C1 C 0.25304(9) 0.13943(10) 0.34920(8) 0.01573(18) Uani 1 1 d . . . C2 C 0.15176(11) 0.05917(11) 0.37810(9) 0.0198(2) Uani 1 1 d . . . H2 H 0.1684 -0.0221 0.4075 0.024 Uiso 1 1 calc R . . C3 C 0.02709(11) 0.10207(13) 0.36247(10) 0.0248(2) Uani 1 1 d . . . H3 H -0.0439 0.0507 0.3817 0.030 Uiso 1 1 calc R . . C4 C 0.00654(11) 0.22101(13) 0.31838(10) 0.0262(2) Uani 1 1 d . . . H4 H -0.0782 0.2528 0.3073 0.031 Uiso 1 1 calc R . . C5 C 0.11302(11) 0.29200(12) 0.29110(9) 0.0229(2) Uani 1 1 d . . . H5 H 0.0987 0.3727 0.2598 0.028 Uiso 1 1 calc R . . C6 C 0.50666(10) 0.21572(10) 0.18452(9) 0.01858(19) Uani 1 1 d . . . H6 H 0.4591 0.2971 0.1780 0.022 Uiso 1 1 calc R . . C7 C 0.43318(13) 0.11771(13) 0.11553(10) 0.0272(2) Uani 1 1 d . . . H7A H 0.4290 0.1447 0.0382 0.041 Uiso 1 1 calc R . . H7B H 0.3456 0.1089 0.1433 0.041 Uiso 1 1 calc R . . H7C H 0.4778 0.0368 0.1209 0.041 Uiso 1 1 calc R . . C8 C 0.64154(12) 0.23470(12) 0.13730(10) 0.0259(2) Uani 1 1 d . . . H8A H 0.6335 0.2630 0.0605 0.039 Uiso 1 1 calc R . . H8B H 0.6889 0.1551 0.1402 0.039 Uiso 1 1 calc R . . H8C H 0.6882 0.2980 0.1811 0.039 Uiso 1 1 calc R . . C9 C 0.52264(10) 0.31873(10) 0.41188(9) 0.01839(19) Uani 1 1 d . . . H9 H 0.4444 0.3694 0.3924 0.022 Uiso 1 1 calc R . . C10 C 0.51898(14) 0.28751(12) 0.53514(10) 0.0292(3) Uani 1 1 d . . . H10A H 0.5175 0.3655 0.5780 0.044 Uiso 1 1 calc R . . H10B H 0.5956 0.2387 0.5562 0.044 Uiso 1 1 calc R . . H10C H 0.4415 0.2383 0.5501 0.044 Uiso 1 1 calc R . . C11 C 0.64181(13) 0.39804(12) 0.38723(11) 0.0275(2) Uani 1 1 d . . . H11A H 0.6483 0.4675 0.4402 0.041 Uiso 1 1 calc R . . H11B H 0.6343 0.4318 0.3121 0.041 Uiso 1 1 calc R . . H11C H 0.7191 0.3455 0.3936 0.041 Uiso 1 1 calc 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 Se1 0.01390(6) 0.02211(7) 0.02140(7) 0.00617(4) 0.00342(4) 0.00521(3) P1 0.01256(11) 0.01518(12) 0.01364(11) 0.00216(8) 0.00140(8) 0.00099(8) N1 0.0182(4) 0.0206(4) 0.0178(4) 0.0006(3) -0.0004(3) 0.0040(3) N2 0.0129(4) 0.0163(4) 0.0189(4) 0.0041(3) 0.0017(3) 0.0008(3) C1 0.0142(4) 0.0201(5) 0.0129(4) -0.0015(3) 0.0005(3) 0.0013(3) C2 0.0167(5) 0.0244(5) 0.0183(5) -0.0005(4) 0.0000(4) -0.0020(4) C3 0.0143(5) 0.0397(7) 0.0204(5) -0.0037(5) 0.0003(4) -0.0027(4) C4 0.0164(5) 0.0419(7) 0.0203(5) -0.0048(5) -0.0016(4) 0.0083(4) C5 0.0226(5) 0.0270(5) 0.0191(5) -0.0023(4) -0.0018(4) 0.0097(4) C6 0.0206(5) 0.0202(5) 0.0150(4) 0.0038(4) 0.0011(4) 0.0008(4) C7 0.0311(6) 0.0344(6) 0.0162(5) -0.0020(4) 0.0010(4) -0.0076(5) C8 0.0255(5) 0.0329(6) 0.0194(5) 0.0061(4) 0.0062(4) -0.0031(5) C9 0.0190(4) 0.0178(5) 0.0184(5) -0.0008(4) 0.0006(4) 0.0008(4) C10 0.0412(7) 0.0285(6) 0.0181(5) -0.0036(4) 0.0058(5) -0.0030(5) C11 0.0283(6) 0.0246(6) 0.0296(6) -0.0030(4) 0.0026(5) -0.0076(5) _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 Se1 P1 2.1136(3) . ? P1 N2 1.6812(9) . ? P1 C9 1.8333(11) . ? P1 C6 1.8384(11) . ? N1 C1 1.3307(14) . ? N1 C5 1.3477(14) . ? N2 C1 1.3963(13) . ? N2 H2N 0.8800 . ? C1 C2 1.4049(15) . ? C2 C3 1.3821(15) . ? C2 H2 0.9500 . ? C3 C4 1.3894(19) . ? C3 H3 0.9500 . ? C4 C5 1.3848(18) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.5310(16) . ? C6 C8 1.5364(16) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5302(16) . ? C9 C11 1.5324(16) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 P1 C9 107.46(5) . . ? N2 P1 C6 108.38(5) . . ? C9 P1 C6 107.71(5) . . ? N2 P1 Se1 105.50(3) . . ? C9 P1 Se1 113.49(4) . . ? C6 P1 Se1 114.00(4) . . ? C1 N1 C5 116.86(10) . . ? C1 N2 P1 127.98(7) . . ? C1 N2 H2N 116.0 . . ? P1 N2 H2N 116.0 . . ? N1 C1 N2 117.36(9) . . ? N1 C1 C2 123.78(10) . . ? N2 C1 C2 118.86(10) . . ? C3 C2 C1 117.93(11) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 119.35(11) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.18(10) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.89(11) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C7 C6 C8 109.55(9) . . ? C7 C6 P1 112.08(8) . . ? C8 C6 P1 111.14(8) . . ? C7 C6 H6 108.0 . . ? C8 C6 H6 108.0 . . ? P1 C6 H6 108.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 110.23(10) . . ? C10 C9 P1 109.39(8) . . ? C11 C9 P1 112.60(8) . . ? C10 C9 H9 108.2 . . ? C11 C9 H9 108.2 . . ? P1 C9 H9 108.2 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C9 P1 N2 C1 61.28(10) . . . . ? C6 P1 N2 C1 -54.86(10) . . . . ? Se1 P1 N2 C1 -177.33(8) . . . . ? C5 N1 C1 N2 179.24(9) . . . . ? C5 N1 C1 C2 0.35(15) . . . . ? P1 N2 C1 N1 -1.61(14) . . . . ? P1 N2 C1 C2 177.34(8) . . . . ? N1 C1 C2 C3 -0.97(16) . . . . ? N2 C1 C2 C3 -179.85(10) . . . . ? C1 C2 C3 C4 0.57(16) . . . . ? C2 C3 C4 C5 0.36(17) . . . . ? C1 N1 C5 C4 0.69(16) . . . . ? C3 C4 C5 N1 -1.05(18) . . . . ? N2 P1 C6 C7 -34.10(9) . . . . ? C9 P1 C6 C7 -150.08(8) . . . . ? Se1 P1 C6 C7 83.03(8) . . . . ? N2 P1 C6 C8 -157.06(8) . . . . ? C9 P1 C6 C8 86.96(9) . . . . ? Se1 P1 C6 C8 -39.93(9) . . . . ? N2 P1 C9 C10 58.58(9) . . . . ? C6 P1 C9 C10 175.15(8) . . . . ? Se1 P1 C9 C10 -57.66(9) . . . . ? N2 P1 C9 C11 -178.50(8) . . . . ? C6 P1 C9 C11 -61.92(9) . . . . ? Se1 P1 C9 C11 65.26(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N Se1 0.88 3.00 3.5903(9) 126.4 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.582 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.058 #===END # 1442tt [CuBr(SPN-Ph)] data_3a-1442 _database_code_depnum_ccdc_archive 'CCDC 810367' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480 #_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1442 (CuBr(SPN-Ph)) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 Br Cu N2 P S' _chemical_formula_sum 'C17 H15 Br Cu N2 P S' _chemical_formula_weight 453.79 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' 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' Br Br -0.2901 2.4595 '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 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 12.6449(15) _cell_length_b 11.8148(14) _cell_length_c 23.312(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.7710(10) _cell_angle_gamma 90.00 _cell_volume 3409.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9859 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.11 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 3.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from dichloromethane / diethyl ether. Bruker Kappa APEX-2 CCD diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 24172 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4952 _reflns_number_gt 4619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0212P)^2^+4.2348P] 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 4952 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0477 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _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 0.225539(13) 0.337366(14) 0.373023(7) 0.01474(4) Uani 1 1 d . . . Br1 Br 0.051701(10) 0.414824(11) 0.349109(6) 0.01542(4) Uani 1 1 d . . . S1 S 0.33445(3) 0.29184(3) 0.456518(15) 0.01794(7) Uani 1 1 d . . . P1 P 0.44958(3) 0.25943(3) 0.412687(14) 0.01186(6) Uani 1 1 d . . . N1 N 0.27358(9) 0.27274(10) 0.30035(5) 0.0145(2) Uani 1 1 d . . . N2 N 0.41916(9) 0.17070(9) 0.35568(5) 0.0136(2) Uani 1 1 d . . . H2N H 0.4544 0.1060 0.3591 0.016 Uiso 1 1 calc R . . C1 C 0.34482(10) 0.18719(11) 0.30353(6) 0.0125(2) Uani 1 1 d . . . C2 C 0.34625(11) 0.11382(11) 0.25641(6) 0.0151(2) Uani 1 1 d . . . H2 H 0.3970 0.0536 0.2600 0.018 Uiso 1 1 calc R . . C3 C 0.27245(11) 0.13083(12) 0.20462(6) 0.0177(3) Uani 1 1 d . . . H3 H 0.2706 0.0812 0.1724 0.021 Uiso 1 1 calc R . . C4 C 0.20049(12) 0.22176(12) 0.20012(6) 0.0185(3) Uani 1 1 d . . . H4 H 0.1506 0.2366 0.1646 0.022 Uiso 1 1 calc R . . C5 C 0.20387(11) 0.28917(12) 0.24850(6) 0.0170(3) Uani 1 1 d . . . H5 H 0.1547 0.3507 0.2455 0.020 Uiso 1 1 calc R . . C6 C 0.56171(10) 0.18687(11) 0.45758(6) 0.0137(2) Uani 1 1 d . . . C7 C 0.55072(11) 0.14023(12) 0.51087(6) 0.0186(3) Uani 1 1 d . . . H7 H 0.4859 0.1506 0.5248 0.022 Uiso 1 1 calc R . . C8 C 0.63584(13) 0.07808(13) 0.54354(7) 0.0234(3) Uani 1 1 d . . . H8 H 0.6293 0.0469 0.5802 0.028 Uiso 1 1 calc R . . C9 C 0.72967(12) 0.06156(13) 0.52290(7) 0.0230(3) Uani 1 1 d . . . H9 H 0.7864 0.0170 0.5448 0.028 Uiso 1 1 calc R . . C10 C 0.74134(12) 0.10984(13) 0.47025(7) 0.0225(3) Uani 1 1 d . . . H10 H 0.8065 0.0995 0.4565 0.027 Uiso 1 1 calc R . . C11 C 0.65785(11) 0.17325(13) 0.43763(6) 0.0181(3) Uani 1 1 d . . . H11 H 0.6661 0.2073 0.4019 0.022 Uiso 1 1 calc R . . C12 C 0.49853(10) 0.38600(11) 0.38345(6) 0.0139(2) Uani 1 1 d . . . C13 C 0.48927(11) 0.49008(12) 0.41046(6) 0.0185(3) Uani 1 1 d . . . H13 H 0.4558 0.4940 0.4434 0.022 Uiso 1 1 calc R . . C14 C 0.52890(13) 0.58790(12) 0.38927(7) 0.0240(3) Uani 1 1 d . . . H14 H 0.5225 0.6586 0.4077 0.029 Uiso 1 1 calc R . . C15 C 0.57769(14) 0.58237(14) 0.34132(8) 0.0274(3) Uani 1 1 d . . . H15 H 0.6036 0.6495 0.3265 0.033 Uiso 1 1 calc R . . C16 C 0.58893(13) 0.47885(14) 0.31476(7) 0.0253(3) Uani 1 1 d . . . H16 H 0.6239 0.4753 0.2824 0.030 Uiso 1 1 calc R . . C17 C 0.54904(12) 0.38054(13) 0.33547(6) 0.0186(3) Uani 1 1 d . . . H17 H 0.5561 0.3100 0.3171 0.022 Uiso 1 1 calc 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 0.01204(8) 0.01423(8) 0.01731(8) -0.00018(6) 0.00148(6) 0.00193(6) Br1 0.01222(6) 0.01400(6) 0.01962(7) 0.00062(5) 0.00228(5) 0.00276(4) S1 0.01366(14) 0.02654(18) 0.01437(15) 0.00170(12) 0.00461(11) 0.00506(12) P1 0.01088(14) 0.01268(14) 0.01183(14) 0.00013(11) 0.00192(11) 0.00171(11) N1 0.0135(5) 0.0139(5) 0.0152(5) -0.0002(4) 0.0010(4) 0.0019(4) N2 0.0136(5) 0.0114(5) 0.0143(5) -0.0011(4) -0.0004(4) 0.0027(4) C1 0.0115(5) 0.0111(5) 0.0148(6) 0.0007(4) 0.0021(4) -0.0005(4) C2 0.0158(6) 0.0129(6) 0.0168(6) -0.0009(5) 0.0036(5) 0.0011(5) C3 0.0201(6) 0.0170(6) 0.0156(6) -0.0027(5) 0.0026(5) 0.0004(5) C4 0.0182(6) 0.0210(7) 0.0149(6) 0.0007(5) 0.0003(5) 0.0015(5) C5 0.0159(6) 0.0174(6) 0.0169(6) 0.0016(5) 0.0013(5) 0.0037(5) C6 0.0120(5) 0.0134(6) 0.0145(6) -0.0009(4) -0.0004(4) 0.0017(4) C7 0.0151(6) 0.0201(7) 0.0201(6) 0.0040(5) 0.0019(5) -0.0004(5) C8 0.0210(7) 0.0240(7) 0.0229(7) 0.0090(6) -0.0012(6) -0.0010(6) C9 0.0177(6) 0.0190(7) 0.0283(7) 0.0029(6) -0.0049(6) 0.0035(5) C10 0.0153(6) 0.0260(7) 0.0249(7) -0.0049(6) 0.0012(5) 0.0062(6) C11 0.0155(6) 0.0230(7) 0.0155(6) -0.0014(5) 0.0028(5) 0.0034(5) C12 0.0120(5) 0.0124(6) 0.0160(6) 0.0008(4) 0.0001(4) 0.0008(4) C13 0.0159(6) 0.0162(6) 0.0210(6) -0.0017(5) -0.0017(5) 0.0033(5) C14 0.0221(7) 0.0137(6) 0.0311(8) -0.0008(5) -0.0066(6) 0.0006(5) C15 0.0245(7) 0.0197(7) 0.0342(8) 0.0088(6) -0.0030(6) -0.0067(6) C16 0.0243(7) 0.0260(8) 0.0257(7) 0.0059(6) 0.0055(6) -0.0060(6) C17 0.0185(6) 0.0180(6) 0.0193(6) 0.0001(5) 0.0043(5) -0.0019(5) _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 N1 2.0597(12) . ? Cu1 S1 2.2092(4) . ? Cu1 Br1 2.3410(3) . ? S1 P1 1.9791(5) . ? P1 N2 1.6746(12) . ? P1 C6 1.7987(13) . ? P1 C12 1.8044(14) . ? N1 C1 1.3458(17) . ? N1 C5 1.3568(17) . ? N2 C1 1.3906(16) . ? N2 H2N 0.8800 . ? C1 C2 1.4023(18) . ? C2 C3 1.3818(19) . ? C2 H2 0.9500 . ? C3 C4 1.398(2) . ? C3 H3 0.9500 . ? C4 C5 1.3743(19) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.3917(19) . ? C6 C11 1.3967(19) . ? C7 C8 1.394(2) . ? C7 H7 0.9500 . ? C8 C9 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.3972(19) . ? C12 C17 1.3981(19) . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 C17 1.391(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? 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 Cu1 S1 113.51(3) . . ? N1 Cu1 Br1 111.67(3) . . ? S1 Cu1 Br1 133.730(12) . . ? P1 S1 Cu1 89.096(19) . . ? N2 P1 C6 100.93(6) . . ? N2 P1 C12 105.07(6) . . ? C6 P1 C12 108.92(6) . . ? N2 P1 S1 117.18(4) . . ? C6 P1 S1 111.56(5) . . ? C12 P1 S1 112.32(5) . . ? C1 N1 C5 117.55(12) . . ? C1 N1 Cu1 122.65(9) . . ? C5 N1 Cu1 115.64(9) . . ? C1 N2 P1 127.66(9) . . ? C1 N2 H2N 116.2 . . ? P1 N2 H2N 116.2 . . ? N1 C1 N2 118.61(11) . . ? N1 C1 C2 122.45(12) . . ? N2 C1 C2 118.94(12) . . ? C3 C2 C1 118.70(12) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.38(13) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.23(13) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.64(13) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C7 C6 C11 120.26(12) . . ? C7 C6 P1 119.85(10) . . ? C11 C6 P1 119.83(11) . . ? C6 C7 C8 119.32(13) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 120.41(14) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.22(14) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.00(14) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C6 119.74(14) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C13 C12 C17 119.67(13) . . ? C13 C12 P1 119.50(11) . . ? C17 C12 P1 120.79(10) . . ? C14 C13 C12 120.15(14) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.01(14) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.25(14) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.15(15) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 119.75(14) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? 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 N1 Cu1 S1 P1 20.00(4) . . . . ? Br1 Cu1 S1 P1 -173.220(15) . . . . ? Cu1 S1 P1 N2 -52.58(5) . . . . ? Cu1 S1 P1 C6 -168.17(5) . . . . ? Cu1 S1 P1 C12 69.21(5) . . . . ? S1 Cu1 N1 C1 17.44(11) . . . . ? Br1 Cu1 N1 C1 -152.32(9) . . . . ? S1 Cu1 N1 C5 173.90(9) . . . . ? Br1 Cu1 N1 C5 4.14(11) . . . . ? C6 P1 N2 C1 -173.18(11) . . . . ? C12 P1 N2 C1 -59.98(12) . . . . ? S1 P1 N2 C1 65.50(12) . . . . ? C5 N1 C1 N2 178.16(12) . . . . ? Cu1 N1 C1 N2 -25.81(16) . . . . ? C5 N1 C1 C2 -2.30(19) . . . . ? Cu1 N1 C1 C2 153.73(10) . . . . ? P1 N2 C1 N1 -13.33(18) . . . . ? P1 N2 C1 C2 167.12(10) . . . . ? N1 C1 C2 C3 0.7(2) . . . . ? N2 C1 C2 C3 -179.78(12) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C2 C3 C4 C5 -2.0(2) . . . . ? C1 N1 C5 C4 1.8(2) . . . . ? Cu1 N1 C5 C4 -155.91(12) . . . . ? C3 C4 C5 N1 0.3(2) . . . . ? N2 P1 C6 C7 -111.89(12) . . . . ? C12 P1 C6 C7 137.85(11) . . . . ? S1 P1 C6 C7 13.31(13) . . . . ? N2 P1 C6 C11 65.29(12) . . . . ? C12 P1 C6 C11 -44.96(13) . . . . ? S1 P1 C6 C11 -169.51(10) . . . . ? C11 C6 C7 C8 -1.2(2) . . . . ? P1 C6 C7 C8 175.98(11) . . . . ? C6 C7 C8 C9 -0.9(2) . . . . ? C7 C8 C9 C10 2.1(2) . . . . ? C8 C9 C10 C11 -1.2(2) . . . . ? C9 C10 C11 C6 -0.9(2) . . . . ? C7 C6 C11 C10 2.1(2) . . . . ? P1 C6 C11 C10 -175.09(11) . . . . ? N2 P1 C12 C13 153.74(11) . . . . ? C6 P1 C12 C13 -98.81(12) . . . . ? S1 P1 C12 C13 25.28(12) . . . . ? N2 P1 C12 C17 -28.59(13) . . . . ? C6 P1 C12 C17 78.86(12) . . . . ? S1 P1 C12 C17 -157.04(10) . . . . ? C17 C12 C13 C14 0.8(2) . . . . ? P1 C12 C13 C14 178.49(11) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C16 -1.1(2) . . . . ? C14 C15 C16 C17 1.4(2) . . . . ? C15 C16 C17 C12 -0.6(2) . . . . ? C13 C12 C17 C16 -0.5(2) . . . . ? P1 C12 C17 C16 -178.14(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N Br1 0.88 2.61 3.4751(12) 169.8 3_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.511 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.063 #===END # 1449 [CuBr(SPN-iPr)] at 296K data_3b-1449 _database_code_depnum_ccdc_archive 'CCDC 810368' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449 #_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1449 (CuBr(SPN-iPr)) at 296K' _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 Br Cu N2 P S' _chemical_formula_sum 'C11 H19 Br Cu N2 P S' _chemical_formula_weight 385.76 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' 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 10.4358(3) _cell_length_b 12.6065(4) _cell_length_c 11.7714(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.938(1) _cell_angle_gamma 90.00 _cell_volume 1546.60(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7163 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.23 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 4.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Thin needle-like crystals from acetone by evaporation. Bruker Kappa APEX-2 CCD diffractometer. Compounds 3b-1449 [CuBr(SPN-iPr)], 5b-1480 [CuI(SPN-iPr)], and 6b-1459 [CuI(SePN-iPr)] are isostructural. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 21214 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3559 _reflns_number_gt 2702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0202P)^2^+0.7214P] 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 3559 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0543 _refine_ls_wR_factor_gt 0.0479 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Br1 Br 0.28764(2) 0.006166(18) 0.002006(19) 0.04047(8) Uani 1 1 d . . . Cu1 Cu 0.25465(3) 0.07544(2) 0.18137(2) 0.04151(9) Uani 1 1 d . . . P1 P 0.16389(5) 0.16571(5) 0.40490(5) 0.03206(13) Uani 1 1 d . . . S1 S 0.07612(6) 0.09465(5) 0.27158(5) 0.04538(16) Uani 1 1 d . . . N1 N 0.41111(18) 0.14753(15) 0.25525(15) 0.0377(4) Uani 1 1 d . . . N2 N 0.28794(16) 0.24513(14) 0.38027(15) 0.0340(4) Uani 1 1 d . . . H2 H 0.2779 0.3097 0.4017 0.041 Uiso 1 1 calc R . . C1 C 0.4042(2) 0.22598(17) 0.33151(17) 0.0315(5) Uani 1 1 d . . . C2 C 0.5093(2) 0.28992(19) 0.3611(2) 0.0424(6) Uani 1 1 d . . . H2A H 0.5022 0.3444 0.4136 0.051 Uiso 1 1 calc R . . C3 C 0.6228(2) 0.2718(2) 0.3123(2) 0.0538(7) Uani 1 1 d . . . H3 H 0.6935 0.3145 0.3304 0.065 Uiso 1 1 calc R . . C4 C 0.6322(3) 0.1894(2) 0.2356(2) 0.0564(7) Uani 1 1 d . . . H4 H 0.7092 0.1748 0.2024 0.068 Uiso 1 1 calc R . . C5 C 0.5250(2) 0.1302(2) 0.2099(2) 0.0476(6) Uani 1 1 d . . . H5 H 0.5311 0.0748 0.1582 0.057 Uiso 1 1 calc R . . C6 C 0.2191(2) 0.06875(19) 0.5113(2) 0.0460(6) Uani 1 1 d . . . H6 H 0.1430 0.0306 0.5347 0.055 Uiso 1 1 calc R . . C7 C 0.3091(3) -0.0138(2) 0.4645(3) 0.0602(8) Uani 1 1 d . . . H7A H 0.3872 0.0200 0.4443 0.090 Uiso 1 1 calc R . . H7B H 0.2686 -0.0465 0.3983 0.090 Uiso 1 1 calc R . . H7C H 0.3281 -0.0669 0.5213 0.090 Uiso 1 1 calc R . . C8 C 0.2786(4) 0.1233(3) 0.6178(2) 0.0828(11) Uani 1 1 d . . . H8A H 0.2999 0.0709 0.6749 0.124 Uiso 1 1 calc R . . H8B H 0.2183 0.1728 0.6465 0.124 Uiso 1 1 calc R . . H8C H 0.3550 0.1603 0.5988 0.124 Uiso 1 1 calc R . . C9 C 0.0559(2) 0.25913(19) 0.4687(2) 0.0404(5) Uani 1 1 d . . . H9 H 0.1045 0.2965 0.5299 0.048 Uiso 1 1 calc R . . C10 C -0.0556(3) 0.2013(2) 0.5214(3) 0.0635(8) Uani 1 1 d . . . H10A H -0.1115 0.2521 0.5540 0.095 Uiso 1 1 calc R . . H10B H -0.0226 0.1539 0.5796 0.095 Uiso 1 1 calc R . . H10C H -0.1027 0.1615 0.4636 0.095 Uiso 1 1 calc R . . C11 C 0.0070(3) 0.3417(2) 0.3821(2) 0.0561(7) Uani 1 1 d . . . H11A H -0.0422 0.3072 0.3217 0.084 Uiso 1 1 calc R . . H11B H 0.0785 0.3778 0.3515 0.084 Uiso 1 1 calc R . . H11C H -0.0462 0.3921 0.4187 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04783(15) 0.03468(13) 0.03998(13) -0.00354(10) 0.01265(10) 0.00330(11) Cu1 0.04609(18) 0.03822(17) 0.04081(16) -0.00778(13) 0.00802(13) -0.00133(13) P1 0.0304(3) 0.0321(3) 0.0341(3) -0.0047(2) 0.0063(2) -0.0037(2) S1 0.0370(3) 0.0569(4) 0.0424(3) -0.0157(3) 0.0038(3) -0.0087(3) N1 0.0359(11) 0.0374(11) 0.0407(10) -0.0086(8) 0.0095(8) -0.0015(9) N2 0.0321(10) 0.0261(9) 0.0448(10) -0.0099(8) 0.0110(8) -0.0022(8) C1 0.0305(12) 0.0292(11) 0.0354(11) -0.0006(9) 0.0071(9) 0.0000(9) C2 0.0356(14) 0.0417(14) 0.0502(14) -0.0128(11) 0.0060(11) -0.0042(11) C3 0.0325(14) 0.0556(17) 0.0742(18) -0.0139(14) 0.0110(13) -0.0092(12) C4 0.0356(15) 0.0655(19) 0.0700(18) -0.0172(15) 0.0206(13) 0.0000(13) C5 0.0430(15) 0.0494(16) 0.0519(15) -0.0157(12) 0.0169(12) 0.0004(12) C6 0.0523(16) 0.0390(14) 0.0465(14) 0.0046(11) 0.0009(12) -0.0036(12) C7 0.0504(17) 0.0528(17) 0.078(2) 0.0189(15) 0.0069(14) 0.0061(13) C8 0.122(3) 0.071(2) 0.0517(18) 0.0044(16) -0.0300(18) -0.004(2) C9 0.0335(13) 0.0421(14) 0.0466(13) -0.0107(11) 0.0132(10) -0.0040(11) C10 0.0495(17) 0.0668(19) 0.0772(19) -0.0112(16) 0.0329(15) -0.0105(15) C11 0.0412(16) 0.0522(16) 0.0754(18) -0.0028(14) 0.0074(13) 0.0113(13) _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 Br1 Cu1 2.3267(4) . ? Cu1 N1 2.0256(19) . ? Cu1 S1 2.2046(7) . ? P1 N2 1.6736(18) . ? P1 C9 1.819(2) . ? P1 C6 1.822(2) . ? P1 S1 1.9892(8) . ? N1 C1 1.340(3) . ? N1 C5 1.346(3) . ? N2 C1 1.390(3) . ? N2 H2 0.8600 . ? C1 C2 1.391(3) . ? C2 C3 1.362(3) . ? C2 H2A 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.524(4) . ? C6 C8 1.533(4) . ? C6 H6 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C11 1.526(4) . ? C9 C10 1.531(3) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 Cu1 S1 115.24(5) . . ? N1 Cu1 Br1 113.86(5) . . ? S1 Cu1 Br1 130.27(2) . . ? N2 P1 C9 100.68(10) . . ? N2 P1 C6 107.46(11) . . ? C9 P1 C6 109.36(11) . . ? N2 P1 S1 117.50(7) . . ? C9 P1 S1 110.31(8) . . ? C6 P1 S1 110.90(8) . . ? P1 S1 Cu1 93.62(3) . . ? C1 N1 C5 117.70(19) . . ? C1 N1 Cu1 123.28(15) . . ? C5 N1 Cu1 117.76(15) . . ? C1 N2 P1 131.84(15) . . ? C1 N2 H2 114.1 . . ? P1 N2 H2 114.1 . . ? N1 C1 N2 118.89(19) . . ? N1 C1 C2 121.77(19) . . ? N2 C1 C2 119.33(19) . . ? C3 C2 C1 119.3(2) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.1(2) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 123.6(2) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C7 C6 C8 111.8(2) . . ? C7 C6 P1 112.86(18) . . ? C8 C6 P1 111.22(19) . . ? C7 C6 H6 106.9 . . ? C8 C6 H6 106.9 . . ? P1 C6 H6 106.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 111.1(2) . . ? C11 C9 P1 111.06(16) . . ? C10 C9 P1 111.02(18) . . ? C11 C9 H9 107.8 . . ? C10 C9 H9 107.8 . . ? P1 C9 H9 107.8 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N2 P1 S1 Cu1 34.77(8) . . . . ? C9 P1 S1 Cu1 149.32(8) . . . . ? C6 P1 S1 Cu1 -89.35(9) . . . . ? N1 Cu1 S1 P1 -6.90(7) . . . . ? Br1 Cu1 S1 P1 -177.10(2) . . . . ? S1 Cu1 N1 C1 -19.29(19) . . . . ? Br1 Cu1 N1 C1 152.55(15) . . . . ? S1 Cu1 N1 C5 173.87(16) . . . . ? Br1 Cu1 N1 C5 -14.3(2) . . . . ? C9 P1 N2 C1 -179.2(2) . . . . ? C6 P1 N2 C1 66.4(2) . . . . ? S1 P1 N2 C1 -59.5(2) . . . . ? C5 N1 C1 N2 -179.6(2) . . . . ? Cu1 N1 C1 N2 13.6(3) . . . . ? C5 N1 C1 C2 1.8(3) . . . . ? Cu1 N1 C1 C2 -165.01(17) . . . . ? P1 N2 C1 N1 27.4(3) . . . . ? P1 N2 C1 C2 -153.95(19) . . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? N2 C1 C2 C3 -179.3(2) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? C1 N1 C5 C4 -1.5(4) . . . . ? Cu1 N1 C5 C4 166.1(2) . . . . ? C3 C4 C5 N1 -0.1(4) . . . . ? N2 P1 C6 C7 -72.3(2) . . . . ? C9 P1 C6 C7 179.23(19) . . . . ? S1 P1 C6 C7 57.3(2) . . . . ? N2 P1 C6 C8 54.2(2) . . . . ? C9 P1 C6 C8 -54.2(2) . . . . ? S1 P1 C6 C8 -176.10(19) . . . . ? N2 P1 C9 C11 67.22(18) . . . . ? C6 P1 C9 C11 -179.83(17) . . . . ? S1 P1 C9 C11 -57.60(18) . . . . ? N2 P1 C9 C10 -168.62(19) . . . . ? C6 P1 C9 C10 -55.7(2) . . . . ? S1 P1 C9 C10 66.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Br1 0.86 2.60 3.4473(17) 167.0 4_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.325 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.061 #===END # 1480 [CuI(SPN-iPr)] at 100K data_5b-1480 _database_code_depnum_ccdc_archive 'CCDC 810369' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_5b480_ #6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1480 (CuI(SPN-iPr)) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 Cu I N2 P S' _chemical_formula_sum 'C11 H19 Cu I N2 P S' _chemical_formula_weight 432.75 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' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.3862(12) _cell_length_b 13.2474(16) _cell_length_c 11.5122(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.4300(10) _cell_angle_gamma 90.00 _cell_volume 1566.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9647 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.07 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 3.582 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from acetone / diethylether by solvent diffusion. Bruker Kappa APEX-2 CCD diffractometer. Compounds 3b-1449 [CuBr(SPN-iPr)], 5b-1480 [CuI(SPN-iPr)], and 6b-1459 [CuI(SePN-iPr)] are isostructural. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 25638 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4544 _reflns_number_gt 4297 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0173P)^2^+1.4873P] 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 4544 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0178 _refine_ls_R_factor_gt 0.0165 _refine_ls_wR_factor_ref 0.0437 _refine_ls_wR_factor_gt 0.0428 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 I1 I 0.265942(9) -0.000132(6) -0.021444(8) 0.01364(3) Uani 1 1 d . . . Cu1 Cu 0.238633(18) 0.074280(14) 0.172647(16) 0.01481(4) Uani 1 1 d . . . P1 P 0.15258(4) 0.15947(3) 0.39503(3) 0.01243(7) Uani 1 1 d . . . S1 S 0.05858(4) 0.09172(3) 0.25312(3) 0.01710(7) Uani 1 1 d . . . N1 N 0.39825(12) 0.14560(9) 0.25533(11) 0.0148(2) Uani 1 1 d . . . N2 N 0.27599(12) 0.23746(9) 0.37720(11) 0.0142(2) Uani 1 1 d . . . H2N H 0.2653 0.3000 0.3998 0.017 Uiso 1 1 calc R . . C1 C 0.39245(14) 0.22070(11) 0.33291(13) 0.0133(2) Uani 1 1 d . . . C2 C 0.49838(14) 0.28512(12) 0.36856(14) 0.0171(3) Uani 1 1 d . . . H2 H 0.4914 0.3382 0.4228 0.020 Uiso 1 1 calc R . . C3 C 0.61271(15) 0.26977(13) 0.32335(15) 0.0209(3) Uani 1 1 d . . . H3 H 0.6852 0.3130 0.3452 0.025 Uiso 1 1 calc R . . C4 C 0.62097(16) 0.19007(13) 0.24504(15) 0.0220(3) Uani 1 1 d . . . H4 H 0.6993 0.1772 0.2141 0.026 Uiso 1 1 calc R . . C5 C 0.51241(15) 0.13075(12) 0.21403(14) 0.0185(3) Uani 1 1 d . . . H5 H 0.5179 0.0766 0.1609 0.022 Uiso 1 1 calc R . . C6 C 0.21470(16) 0.06757(12) 0.50817(14) 0.0183(3) Uani 1 1 d . . . H6 H 0.1379 0.0298 0.5290 0.022 Uiso 1 1 calc R . . C7 C 0.30533(18) -0.01031(13) 0.46390(18) 0.0245(3) Uani 1 1 d . . . H7A H 0.3849 0.0233 0.4479 0.037 Uiso 1 1 calc R . . H7B H 0.2613 -0.0415 0.3916 0.037 Uiso 1 1 calc R . . H7C H 0.3277 -0.0624 0.5239 0.037 Uiso 1 1 calc R . . C8 C 0.2797(2) 0.11991(15) 0.62015(16) 0.0311(4) Uani 1 1 d . . . H8A H 0.3019 0.0696 0.6822 0.047 Uiso 1 1 calc R . . H8B H 0.2198 0.1697 0.6454 0.047 Uiso 1 1 calc R . . H8C H 0.3592 0.1540 0.6045 0.047 Uiso 1 1 calc R . . C9 C 0.04507(14) 0.24764(11) 0.45589(14) 0.0159(3) Uani 1 1 d . . . H9 H 0.0983 0.2870 0.5198 0.019 Uiso 1 1 calc R . . C10 C -0.06185(16) 0.19197(13) 0.50896(15) 0.0219(3) Uani 1 1 d . . . H10A H -0.1174 0.2412 0.5414 0.033 Uiso 1 1 calc R . . H10B H -0.0219 0.1469 0.5716 0.033 Uiso 1 1 calc R . . H10C H -0.1146 0.1522 0.4478 0.033 Uiso 1 1 calc R . . C11 C -0.01457(15) 0.32192(12) 0.36061(15) 0.0202(3) Uani 1 1 d . . . H11A H -0.0714 0.2852 0.2994 0.030 Uiso 1 1 calc R . . H11B H 0.0551 0.3551 0.3260 0.030 Uiso 1 1 calc R . . H11C H -0.0655 0.3729 0.3956 0.030 Uiso 1 1 calc 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 I1 0.01724(5) 0.01187(5) 0.01242(5) -0.00109(3) 0.00421(3) 0.00061(3) Cu1 0.01645(9) 0.01437(8) 0.01394(9) -0.00329(6) 0.00334(6) -0.00080(6) P1 0.01263(16) 0.01228(15) 0.01263(16) -0.00208(12) 0.00272(12) -0.00123(12) S1 0.01417(16) 0.02073(17) 0.01640(17) -0.00690(13) 0.00221(12) -0.00221(13) N1 0.0148(6) 0.0151(5) 0.0150(6) -0.0029(4) 0.0036(4) 0.0000(4) N2 0.0135(5) 0.0122(5) 0.0178(6) -0.0039(4) 0.0054(4) -0.0016(4) C1 0.0133(6) 0.0137(6) 0.0134(6) -0.0007(5) 0.0034(5) 0.0003(5) C2 0.0145(6) 0.0180(7) 0.0188(7) -0.0060(5) 0.0025(5) -0.0016(5) C3 0.0147(7) 0.0229(7) 0.0255(8) -0.0074(6) 0.0047(6) -0.0028(6) C4 0.0157(7) 0.0261(8) 0.0253(8) -0.0086(6) 0.0069(6) -0.0007(6) C5 0.0172(7) 0.0208(7) 0.0182(7) -0.0068(6) 0.0049(5) 0.0008(5) C6 0.0201(7) 0.0165(7) 0.0177(7) 0.0027(5) 0.0007(5) -0.0023(5) C7 0.0230(8) 0.0206(7) 0.0306(9) 0.0072(6) 0.0061(7) 0.0031(6) C8 0.0415(11) 0.0318(9) 0.0170(8) 0.0027(7) -0.0060(7) -0.0034(8) C9 0.0152(6) 0.0159(6) 0.0175(7) -0.0040(5) 0.0055(5) -0.0015(5) C10 0.0206(7) 0.0229(7) 0.0246(8) -0.0027(6) 0.0110(6) -0.0039(6) C11 0.0162(7) 0.0185(7) 0.0267(8) -0.0005(6) 0.0054(6) 0.0028(5) _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 I1 Cu1 2.4961(3) . ? Cu1 N1 2.0209(13) . ? Cu1 S1 2.2174(5) . ? P1 N2 1.6822(13) . ? P1 C9 1.8252(15) . ? P1 C6 1.8300(16) . ? P1 S1 1.9900(5) . ? N1 C1 1.3442(18) . ? N1 C5 1.3550(19) . ? N2 C1 1.3975(18) . ? N2 H2N 0.8800 . ? C1 C2 1.405(2) . ? C2 C3 1.380(2) . ? C2 H2 0.9500 . ? C3 C4 1.399(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C8 1.531(2) . ? C6 C7 1.533(2) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.533(2) . ? C9 C11 1.535(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 Cu1 S1 116.00(4) . . ? N1 Cu1 I1 114.41(4) . . ? S1 Cu1 I1 128.946(13) . . ? N2 P1 C9 100.01(6) . . ? N2 P1 C6 107.46(7) . . ? C9 P1 C6 108.92(7) . . ? N2 P1 S1 117.89(5) . . ? C9 P1 S1 110.47(5) . . ? C6 P1 S1 111.32(5) . . ? P1 S1 Cu1 92.73(2) . . ? C1 N1 C5 117.86(13) . . ? C1 N1 Cu1 123.05(10) . . ? C5 N1 Cu1 117.81(10) . . ? C1 N2 P1 131.50(10) . . ? C1 N2 H2N 114.2 . . ? P1 N2 H2N 114.2 . . ? N1 C1 N2 119.05(13) . . ? N1 C1 C2 122.28(13) . . ? N2 C1 C2 118.64(13) . . ? C3 C2 C1 118.72(14) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.46(15) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.18(14) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.45(14) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C8 C6 C7 111.59(15) . . ? C8 C6 P1 111.35(11) . . ? C7 C6 P1 112.37(12) . . ? C8 C6 H6 107.1 . . ? C7 C6 H6 107.1 . . ? P1 C6 H6 107.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 110.68(13) . . ? C10 C9 P1 111.40(11) . . ? C11 C9 P1 109.96(11) . . ? C10 C9 H9 108.2 . . ? C11 C9 H9 108.2 . . ? P1 C9 H9 108.2 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N2 P1 S1 Cu1 36.06(5) . . . . ? C9 P1 S1 Cu1 150.10(5) . . . . ? C6 P1 S1 Cu1 -88.75(6) . . . . ? N1 Cu1 S1 P1 -8.35(5) . . . . ? I1 Cu1 S1 P1 -178.528(15) . . . . ? S1 Cu1 N1 C1 -18.01(13) . . . . ? I1 Cu1 N1 C1 153.61(11) . . . . ? S1 Cu1 N1 C5 175.21(10) . . . . ? I1 Cu1 N1 C5 -13.17(13) . . . . ? C9 P1 N2 C1 -179.33(14) . . . . ? C6 P1 N2 C1 67.06(15) . . . . ? S1 P1 N2 C1 -59.65(15) . . . . ? C5 N1 C1 N2 -179.79(14) . . . . ? Cu1 N1 C1 N2 13.44(19) . . . . ? C5 N1 C1 C2 2.2(2) . . . . ? Cu1 N1 C1 C2 -164.61(12) . . . . ? P1 N2 C1 N1 26.5(2) . . . . ? P1 N2 C1 C2 -155.41(12) . . . . ? N1 C1 C2 C3 -0.8(2) . . . . ? N2 C1 C2 C3 -178.89(15) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C1 N1 C5 C4 -1.8(2) . . . . ? Cu1 N1 C5 C4 165.71(14) . . . . ? C3 C4 C5 N1 0.0(3) . . . . ? N2 P1 C6 C8 52.99(14) . . . . ? C9 P1 C6 C8 -54.48(14) . . . . ? S1 P1 C6 C8 -176.53(11) . . . . ? N2 P1 C6 C7 -73.03(13) . . . . ? C9 P1 C6 C7 179.49(12) . . . . ? S1 P1 C6 C7 57.44(13) . . . . ? N2 P1 C9 C10 -166.17(11) . . . . ? C6 P1 C9 C10 -53.68(13) . . . . ? S1 P1 C9 C10 68.88(12) . . . . ? N2 P1 C9 C11 70.74(11) . . . . ? C6 P1 C9 C11 -176.77(10) . . . . ? S1 P1 C9 C11 -54.21(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N I1 0.88 2.80 3.6765(13) 172.7 4_566 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.001 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.081 #===END # 1459 [CuI(SePN-iPr)] at 296K data_6b-1459 _database_code_depnum_ccdc_archive 'CCDC 810370' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_ #3b449_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1459 (CuI(SePN-iPr)) at 296K' _chemical_melting_point ? _chemical_formula_moiety 'C11 H19 Cu I N2 P Se' _chemical_formula_sum 'C11 H19 Cu I N2 P Se' _chemical_formula_weight 479.65 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' P P 0.1023 0.0942 '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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.4116(6) _cell_length_b 13.4179(7) _cell_length_c 11.6623(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.501(2) _cell_angle_gamma 90.00 _cell_volume 1615.30(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4602 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 25.76 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 5.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Thin needles from acetone by evaporation. Bruker Kappa APEX-2 CCD diffractometer. Compounds 3b-1449 [CuBr(SPN-iPr)], 5b-1480 [CuI(SPN-iPr)], and 6b-1459 [CuI(SePN-iPr)] are isostructural. ; _diffrn_ambient_temperature 296(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 11943 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 25.96 _reflns_number_total 3142 _reflns_number_gt 2459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0628P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3142 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 I1 I 0.27006(3) 0.00192(2) -0.01901(3) 0.04027(15) Uani 1 1 d . . . Cu1 Cu 0.24052(6) 0.07471(4) 0.17263(5) 0.04070(19) Uani 1 1 d . . . P1 P 0.15330(11) 0.15873(9) 0.40037(9) 0.0321(3) Uani 1 1 d . . . Se1 Se 0.04857(5) 0.08563(4) 0.25341(4) 0.04318(17) Uani 1 1 d . . . N1 N 0.3962(4) 0.1458(3) 0.2558(3) 0.0374(9) Uani 1 1 d . . . N2 N 0.2742(4) 0.2360(3) 0.3772(3) 0.0349(9) Uani 1 1 d . . . H2N H 0.2623 0.2967 0.3969 0.042 Uiso 1 1 calc R . . C1 C 0.3896(4) 0.2205(3) 0.3325(4) 0.0330(10) Uani 1 1 d . . . C2 C 0.4944(5) 0.2825(3) 0.3666(5) 0.0450(12) Uani 1 1 d . . . H2 H 0.4877 0.3335 0.4195 0.054 Uiso 1 1 calc R . . C3 C 0.6074(5) 0.2677(4) 0.3217(5) 0.0600(16) Uani 1 1 d . . . H3 H 0.6776 0.3096 0.3428 0.072 Uiso 1 1 calc R . . C4 C 0.6178(5) 0.1913(4) 0.2456(5) 0.0572(15) Uani 1 1 d . . . H4 H 0.6951 0.1795 0.2159 0.069 Uiso 1 1 calc R . . C5 C 0.5106(5) 0.1326(4) 0.2145(4) 0.0473(13) Uani 1 1 d . . . H5 H 0.5171 0.0810 0.1622 0.057 Uiso 1 1 calc R . . C6 C 0.2180(5) 0.0692(4) 0.5106(4) 0.0485(13) Uani 1 1 d . . . H6 H 0.1442 0.0319 0.5328 0.058 Uiso 1 1 calc R . . C7 C 0.3097(7) -0.0078(4) 0.4641(7) 0.0659(18) Uani 1 1 d . . . H7A H 0.3865 0.0253 0.4466 0.099 Uiso 1 1 calc R . . H7B H 0.2664 -0.0384 0.3952 0.099 Uiso 1 1 calc R . . H7C H 0.3329 -0.0581 0.5217 0.099 Uiso 1 1 calc R . . C8 C 0.2828(8) 0.1205(5) 0.6189(5) 0.086(2) Uani 1 1 d . . . H8A H 0.3040 0.0720 0.6789 0.129 Uiso 1 1 calc R . . H8B H 0.2249 0.1692 0.6439 0.129 Uiso 1 1 calc R . . H8C H 0.3606 0.1529 0.6024 0.129 Uiso 1 1 calc R . . C9 C 0.0475(5) 0.2448(3) 0.4638(4) 0.0409(12) Uani 1 1 d . . . H9 H 0.1005 0.2818 0.5252 0.049 Uiso 1 1 calc R . . C10 C -0.0570(6) 0.1898(5) 0.5183(5) 0.0634(16) Uani 1 1 d . . . H10A H -0.1114 0.2371 0.5506 0.095 Uiso 1 1 calc R . . H10B H -0.0173 0.1467 0.5784 0.095 Uiso 1 1 calc R . . H10C H -0.1084 0.1508 0.4604 0.095 Uiso 1 1 calc R . . C11 C -0.0121(5) 0.3200(4) 0.3737(5) 0.0570(14) Uani 1 1 d . . . H11A H -0.0626 0.2853 0.3114 0.086 Uiso 1 1 calc R . . H11B H 0.0557 0.3566 0.3442 0.086 Uiso 1 1 calc R . . H11C H -0.0667 0.3652 0.4089 0.086 Uiso 1 1 calc 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 I1 0.0509(2) 0.0320(2) 0.0402(2) -0.00427(11) 0.01455(16) 0.00134(14) Cu1 0.0472(4) 0.0351(4) 0.0410(3) -0.0087(2) 0.0103(3) -0.0021(3) P1 0.0349(7) 0.0274(6) 0.0345(6) -0.0045(5) 0.0071(5) -0.0028(5) Se1 0.0389(3) 0.0482(3) 0.0428(3) -0.0154(2) 0.0065(2) -0.0079(2) N1 0.033(2) 0.037(2) 0.043(2) -0.0075(17) 0.0082(17) -0.0002(18) N2 0.035(2) 0.023(2) 0.049(2) -0.0099(16) 0.0147(18) -0.0029(17) C1 0.034(3) 0.028(2) 0.038(2) -0.0004(18) 0.008(2) 0.001(2) C2 0.039(3) 0.038(3) 0.058(3) -0.018(2) 0.008(2) -0.001(2) C3 0.039(3) 0.063(4) 0.078(4) -0.029(3) 0.008(3) -0.009(3) C4 0.034(3) 0.069(4) 0.071(4) -0.023(3) 0.016(3) -0.003(3) C5 0.043(3) 0.046(3) 0.054(3) -0.019(2) 0.011(2) 0.004(3) C6 0.055(3) 0.038(3) 0.051(3) 0.007(2) -0.001(3) -0.003(2) C7 0.059(4) 0.052(4) 0.085(5) 0.024(3) 0.004(3) 0.013(3) C8 0.123(6) 0.070(4) 0.055(4) 0.012(3) -0.029(4) -0.006(4) C9 0.041(3) 0.033(3) 0.053(3) -0.013(2) 0.021(2) -0.006(2) C10 0.057(4) 0.068(4) 0.073(4) -0.014(3) 0.038(3) -0.012(3) C11 0.046(3) 0.042(3) 0.086(4) -0.007(3) 0.019(3) 0.005(3) _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 I1 Cu1 2.4946(6) . ? Cu1 N1 2.017(4) . ? Cu1 Se1 2.3226(8) . ? P1 N2 1.680(4) . ? P1 C9 1.818(5) . ? P1 C6 1.824(5) . ? P1 Se1 2.1449(12) . ? N1 C1 1.351(5) . ? N1 C5 1.354(6) . ? N2 C1 1.387(6) . ? N2 H2N 0.8600 . ? C1 C2 1.389(6) . ? C2 C3 1.363(7) . ? C2 H2 0.9300 . ? C3 C4 1.369(7) . ? C3 H3 0.9300 . ? C4 C5 1.376(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.517(8) . ? C6 C7 1.552(8) . ? C6 H6 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.521(7) . ? C9 C11 1.529(8) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 Cu1 Se1 117.07(11) . . ? N1 Cu1 I1 115.52(11) . . ? Se1 Cu1 I1 126.97(3) . . ? N2 P1 C9 100.4(2) . . ? N2 P1 C6 107.7(2) . . ? C9 P1 C6 108.6(2) . . ? N2 P1 Se1 117.87(14) . . ? C9 P1 Se1 110.11(18) . . ? C6 P1 Se1 111.38(17) . . ? P1 Se1 Cu1 88.76(4) . . ? C1 N1 C5 117.1(4) . . ? C1 N1 Cu1 124.2(3) . . ? C5 N1 Cu1 117.1(3) . . ? C1 N2 P1 132.3(3) . . ? C1 N2 H2N 113.9 . . ? P1 N2 H2N 113.9 . . ? N1 C1 N2 118.8(4) . . ? N1 C1 C2 121.9(4) . . ? N2 C1 C2 119.3(4) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 118.0(5) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 C4 123.5(4) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.3 . . ? C8 C6 C7 111.5(5) . . ? C8 C6 P1 111.8(4) . . ? C7 C6 P1 112.3(4) . . ? C8 C6 H6 107.0 . . ? C7 C6 H6 107.0 . . ? P1 C6 H6 107.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 111.0(5) . . ? C10 C9 P1 111.5(4) . . ? C11 C9 P1 110.6(3) . . ? C10 C9 H9 107.8 . . ? C11 C9 H9 107.8 . . ? P1 C9 H9 107.8 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N2 P1 Se1 Cu1 35.59(16) . . . . ? C9 P1 Se1 Cu1 149.83(17) . . . . ? C6 P1 Se1 Cu1 -89.6(2) . . . . ? N1 Cu1 Se1 P1 -7.00(13) . . . . ? I1 Cu1 Se1 P1 -178.95(4) . . . . ? Se1 Cu1 N1 C1 -20.1(4) . . . . ? I1 Cu1 N1 C1 152.8(3) . . . . ? Se1 Cu1 N1 C5 174.6(3) . . . . ? I1 Cu1 N1 C5 -12.6(4) . . . . ? C9 P1 N2 C1 178.7(4) . . . . ? C6 P1 N2 C1 65.2(5) . . . . ? Se1 P1 N2 C1 -61.8(5) . . . . ? C5 N1 C1 N2 -179.6(4) . . . . ? Cu1 N1 C1 N2 15.0(6) . . . . ? C5 N1 C1 C2 0.9(7) . . . . ? Cu1 N1 C1 C2 -164.5(4) . . . . ? P1 N2 C1 N1 28.1(6) . . . . ? P1 N2 C1 C2 -152.4(4) . . . . ? N1 C1 C2 C3 0.0(8) . . . . ? N2 C1 C2 C3 -179.4(5) . . . . ? C1 C2 C3 C4 -1.3(9) . . . . ? C2 C3 C4 C5 1.6(9) . . . . ? C1 N1 C5 C4 -0.6(8) . . . . ? Cu1 N1 C5 C4 165.8(4) . . . . ? C3 C4 C5 N1 -0.6(9) . . . . ? N2 P1 C6 C8 54.0(5) . . . . ? C9 P1 C6 C8 -53.9(5) . . . . ? Se1 P1 C6 C8 -175.3(4) . . . . ? N2 P1 C6 C7 -72.2(4) . . . . ? C9 P1 C6 C7 179.9(4) . . . . ? Se1 P1 C6 C7 58.5(4) . . . . ? N2 P1 C9 C10 -167.3(4) . . . . ? C6 P1 C9 C10 -54.5(5) . . . . ? Se1 P1 C9 C10 67.7(4) . . . . ? N2 P1 C9 C11 68.6(4) . . . . ? C6 P1 C9 C11 -178.6(4) . . . . ? Se1 P1 C9 C11 -56.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N I1 0.86 2.87 3.721(3) 169.7 4_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.393 _refine_diff_density_min -0.861 _refine_diff_density_rms 0.152 #===END # 1528 [Cu(NHC)(SPN-Ph)]SbF6.((CH3)2CO) data_7a-1528 _database_code_depnum_ccdc_archive 'CCDC 810371' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_ #5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1528 (Cu(NHC)(SPN-Ph))SbF6.((CH3)2CO) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C44 H51 Cu N4 P S, C3 H6 O, F6 Sb' _chemical_formula_sum 'C47 H57 Cu F6 N4 O P S Sb' _chemical_formula_weight 1056.29 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8052(5) _cell_length_b 28.0150(12) _cell_length_c 13.2949(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.056(2) _cell_angle_gamma 90.00 _cell_volume 4766.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9827 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 30.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 1.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Colourless plates from acetone. Bruker Kappa APEX-2 CCD diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 57145 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 30.00 _reflns_number_total 13615 _reflns_number_gt 11492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0337P)^2^+4.3978P] 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 13615 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _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 0.20859(2) 0.552292(10) 0.73292(2) 0.01633(7) Uani 1 1 d U . . S1 S 0.32718(5) 0.49496(2) 0.69878(5) 0.02355(13) Uani 1 1 d U . . P1 P 0.28590(5) 0.45522(2) 0.81327(5) 0.01624(11) Uani 1 1 d U . . N1 N 0.10088(16) 0.52445(7) 0.82685(16) 0.0166(3) Uani 1 1 d U . . N2 N 0.15864(16) 0.44438(7) 0.82328(17) 0.0170(3) Uani 1 1 d U . . H2N H 0.1383 0.4146 0.8155 0.020 Uiso 1 1 calc R . . N3 N 0.26725(16) 0.65227(7) 0.69009(16) 0.0159(3) Uani 1 1 d U . . N4 N 0.15472(16) 0.62624(7) 0.58107(15) 0.0149(3) Uani 1 1 d U . . C1 C 0.08109(18) 0.47791(8) 0.84283(18) 0.0151(3) Uani 1 1 d U . . C2 C -0.01480(19) 0.46150(9) 0.87632(19) 0.0181(4) Uani 1 1 d U . . H2 H -0.0264 0.4283 0.8859 0.022 Uiso 1 1 calc R . . C3 C -0.0922(2) 0.49405(9) 0.8952(2) 0.0209(4) Uani 1 1 d U . . H3 H -0.1581 0.4837 0.9175 0.025 Uiso 1 1 calc R . . C4 C -0.0722(2) 0.54265(9) 0.8811(2) 0.0216(4) Uani 1 1 d U . . H4 H -0.1241 0.5659 0.8941 0.026 Uiso 1 1 calc R . . C5 C 0.0234(2) 0.55607(9) 0.84820(19) 0.0194(4) Uani 1 1 d U . . H5 H 0.0367 0.5892 0.8397 0.023 Uiso 1 1 calc R . . C6 C 0.32819(18) 0.48011(8) 0.9335(2) 0.0167(4) Uani 1 1 d U . . C7 C 0.36620(19) 0.52683(8) 0.9424(2) 0.0196(4) Uani 1 1 d U . . H7 H 0.3702 0.5465 0.8845 0.024 Uiso 1 1 calc R . . C8 C 0.3981(2) 0.54430(9) 1.0367(2) 0.0246(5) Uani 1 1 d U . . H8 H 0.4229 0.5762 1.0430 0.030 Uiso 1 1 calc R . . C9 C 0.3939(2) 0.51570(10) 1.1210(2) 0.0239(5) Uani 1 1 d U . . H9 H 0.4163 0.5280 1.1848 0.029 Uiso 1 1 calc R . . C10 C 0.3573(2) 0.46917(10) 1.1133(2) 0.0234(5) Uani 1 1 d U . . H10 H 0.3543 0.4497 1.1715 0.028 Uiso 1 1 calc R . . C11 C 0.3250(2) 0.45128(9) 1.0194(2) 0.0196(4) Uani 1 1 d U . . H11 H 0.3006 0.4193 1.0136 0.024 Uiso 1 1 calc R . . C12 C 0.33978(19) 0.39607(8) 0.8023(2) 0.0183(4) Uani 1 1 d U . . C13 C 0.4242(2) 0.38951(10) 0.7407(3) 0.0290(6) Uani 1 1 d U . . H13 H 0.4505 0.4157 0.7040 0.035 Uiso 1 1 calc R . . C14 C 0.4703(3) 0.34459(11) 0.7325(3) 0.0378(7) Uani 1 1 d U . . H14 H 0.5277 0.3402 0.6901 0.045 Uiso 1 1 calc R . . C15 C 0.4322(2) 0.30636(10) 0.7865(3) 0.0317(6) Uani 1 1 d U . . H15 H 0.4640 0.2758 0.7816 0.038 Uiso 1 1 calc R . . C16 C 0.3489(2) 0.31252(9) 0.8469(2) 0.0256(5) Uani 1 1 d U . . H16 H 0.3231 0.2862 0.8836 0.031 Uiso 1 1 calc R . . C17 C 0.3013(2) 0.35714(9) 0.8552(2) 0.0202(4) Uani 1 1 d U . . H17 H 0.2430 0.3610 0.8966 0.024 Uiso 1 1 calc R . . C18 C 0.20885(18) 0.61288(8) 0.66660(18) 0.0139(3) Uani 1 1 d U . . C19 C 0.2508(2) 0.68865(8) 0.6203(2) 0.0207(5) Uani 1 1 d U . . H19 H 0.2832 0.7192 0.6209 0.025 Uiso 1 1 calc R . . C20 C 0.1800(2) 0.67214(8) 0.5518(2) 0.0191(4) Uani 1 1 d U . . H20 H 0.1525 0.6887 0.4944 0.023 Uiso 1 1 calc R . . C21 C 0.34941(18) 0.65412(8) 0.76720(19) 0.0163(3) Uani 1 1 d U . . C22 C 0.45199(19) 0.64708(8) 0.7359(2) 0.0189(4) Uani 1 1 d U . . C23 C 0.5324(2) 0.65143(9) 0.8097(2) 0.0233(4) Uani 1 1 d U . . H23 H 0.6028 0.6471 0.7916 0.028 Uiso 1 1 calc R . . C24 C 0.5106(2) 0.66200(10) 0.9087(2) 0.0249(5) Uani 1 1 d U . . H24 H 0.5661 0.6648 0.9577 0.030 Uiso 1 1 calc R . . C25 C 0.4083(2) 0.66850(9) 0.9365(2) 0.0222(4) Uani 1 1 d U . . H25 H 0.3947 0.6756 1.0046 0.027 Uiso 1 1 calc R . . C26 C 0.3248(2) 0.66476(8) 0.8661(2) 0.0188(4) Uani 1 1 d U . . C27 C 0.4784(2) 0.63594(10) 0.6282(2) 0.0234(4) Uani 1 1 d U . . H27 H 0.4113 0.6343 0.5875 0.028 Uiso 1 1 calc R . . C28 C 0.5324(2) 0.58742(10) 0.6203(3) 0.0307(6) Uani 1 1 d U . . H28A H 0.5994 0.5882 0.6583 0.046 Uiso 1 1 calc R . . H28B H 0.5446 0.5804 0.5494 0.046 Uiso 1 1 calc R . . H28C H 0.4879 0.5626 0.6480 0.046 Uiso 1 1 calc R . . C29 C 0.5456(3) 0.67527(11) 0.5831(2) 0.0307(6) Uani 1 1 d U . . H29A H 0.5078 0.7057 0.5843 0.046 Uiso 1 1 calc R . . H29B H 0.5607 0.6671 0.5134 0.046 Uiso 1 1 calc R . . H29C H 0.6114 0.6782 0.6226 0.046 Uiso 1 1 calc R . . C30 C 0.2140(2) 0.67336(9) 0.8984(2) 0.0224(4) Uani 1 1 d U . . H30 H 0.1657 0.6669 0.8391 0.027 Uiso 1 1 calc R . . C31 C 0.1851(2) 0.63903(11) 0.9830(2) 0.0289(5) Uani 1 1 d U . . H31A H 0.1952 0.6060 0.9609 0.043 Uiso 1 1 calc R . . H31B H 0.1118 0.6438 0.9993 0.043 Uiso 1 1 calc R . . H31C H 0.2299 0.6453 1.0429 0.043 Uiso 1 1 calc R . . C32 C 0.1982(2) 0.72524(10) 0.9305(3) 0.0324(6) Uani 1 1 d U . . H32A H 0.2456 0.7326 0.9880 0.049 Uiso 1 1 calc R . . H32B H 0.1257 0.7298 0.9499 0.049 Uiso 1 1 calc R . . H32C H 0.2131 0.7465 0.8744 0.049 Uiso 1 1 calc R . . C33 C 0.08871(18) 0.59471(8) 0.52032(18) 0.0153(3) Uani 1 1 d U . . C34 C 0.1379(2) 0.56447(9) 0.45171(19) 0.0191(4) Uani 1 1 d U . . C35 C 0.0715(2) 0.53526(10) 0.3930(2) 0.0249(5) Uani 1 1 d U . . H35 H 0.1008 0.5138 0.3464 0.030 Uiso 1 1 calc R . . C36 C -0.0353(2) 0.53683(10) 0.4012(2) 0.0252(5) Uani 1 1 d U . . H36 H -0.0784 0.5162 0.3610 0.030 Uiso 1 1 calc R . . C37 C -0.0802(2) 0.56785(10) 0.4670(2) 0.0222(4) Uani 1 1 d U . . H37 H -0.1541 0.5692 0.4698 0.027 Uiso 1 1 calc R . . C38 C -0.01896(19) 0.59756(9) 0.53004(18) 0.0172(4) Uani 1 1 d U . . C39 C 0.2546(2) 0.56451(11) 0.4389(3) 0.0321(6) Uani 1 1 d U . . H39 H 0.2886 0.5770 0.5025 0.039 Uiso 1 1 calc R . . C40 C 0.3000(3) 0.51550(11) 0.4186(3) 0.0340(6) Uani 1 1 d U . . H40A H 0.2784 0.4931 0.4706 0.051 Uiso 1 1 calc R . . H40B H 0.3765 0.5175 0.4198 0.051 Uiso 1 1 calc R . . H40C H 0.2745 0.5042 0.3524 0.051 Uiso 1 1 calc R . . C41 C 0.2819(4) 0.59832(14) 0.3536(5) 0.0762(18) Uani 1 1 d U . . H41A H 0.2459 0.5880 0.2910 0.114 Uiso 1 1 calc R . . H41B H 0.3575 0.5979 0.3449 0.114 Uiso 1 1 calc R . . H41C H 0.2597 0.6308 0.3700 0.114 Uiso 1 1 calc R . . C42 C -0.0696(2) 0.63099(9) 0.6034(2) 0.0212(4) Uani 1 1 d U . . H42 H -0.0167 0.6388 0.6580 0.025 Uiso 1 1 calc R . . C43 C -0.1639(2) 0.60845(10) 0.6522(2) 0.0269(5) Uani 1 1 d U . . H43A H -0.2207 0.6044 0.6016 0.040 Uiso 1 1 calc R . . H43B H -0.1873 0.6292 0.7063 0.040 Uiso 1 1 calc R . . H43C H -0.1442 0.5772 0.6802 0.040 Uiso 1 1 calc R . . C44 C -0.1024(3) 0.67780(11) 0.5512(3) 0.0404(8) Uani 1 1 d U . . H44A H -0.1530 0.6709 0.4960 0.061 Uiso 1 1 calc R . . H44B H -0.0407 0.6933 0.5243 0.061 Uiso 1 1 calc R . . H44C H -0.1344 0.6990 0.6000 0.061 Uiso 1 1 calc R . . Sb1 Sb 0.660646(14) 0.211442(6) 0.606453(14) 0.02111(5) Uani 1 1 d U . . F1 F 0.53865(15) 0.18573(8) 0.65671(17) 0.0439(4) Uani 1 1 d U . . F2 F 0.6092(2) 0.27324(7) 0.61760(18) 0.0527(5) Uani 1 1 d U . . F3 F 0.78506(15) 0.23599(6) 0.55655(16) 0.0350(4) Uani 1 1 d U . . F4 F 0.71433(14) 0.14955(6) 0.59341(15) 0.0310(3) Uani 1 1 d U . . F5 F 0.60535(18) 0.20809(8) 0.47439(16) 0.0451(5) Uani 1 1 d U . . F6 F 0.72068(17) 0.21509(7) 0.73626(15) 0.0369(4) Uani 1 1 d U . . O1 O 0.0349(2) 0.36092(8) 0.7784(2) 0.0410(6) Uani 1 1 d U . . C45 C 0.0083(2) 0.32063(9) 0.7587(2) 0.0253(5) Uani 1 1 d U . . C46 C -0.0993(3) 0.30342(15) 0.7715(3) 0.0483(9) Uani 1 1 d U . . H46A H -0.1235 0.2863 0.7107 0.072 Uiso 1 1 calc R . . H46B H -0.1454 0.3307 0.7828 0.072 Uiso 1 1 calc R . . H46C H -0.1005 0.2818 0.8294 0.072 Uiso 1 1 calc R . . C47 C 0.0836(3) 0.28504(13) 0.7208(3) 0.0427(8) Uani 1 1 d U . . H47A H 0.1515 0.3004 0.7121 0.064 Uiso 1 1 calc R . . H47B H 0.0573 0.2724 0.6559 0.064 Uiso 1 1 calc R . . H47C H 0.0917 0.2588 0.7692 0.064 Uiso 1 1 calc 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 0.01677(14) 0.01567(13) 0.01626(14) 0.00231(10) -0.00354(11) -0.00320(10) S1 0.0214(3) 0.0242(3) 0.0252(3) 0.0051(2) 0.0042(2) 0.0011(2) P1 0.0126(3) 0.0175(2) 0.0186(3) 0.0014(2) -0.0001(2) -0.0013(2) N1 0.0170(8) 0.0170(6) 0.0157(9) 0.0010(6) -0.0015(6) -0.0012(5) N2 0.0126(6) 0.0164(7) 0.0218(10) -0.0001(7) -0.0020(6) -0.0018(5) N3 0.0123(7) 0.0144(7) 0.0205(8) 0.0014(6) -0.0045(7) -0.0008(6) N4 0.0136(8) 0.0167(7) 0.0140(8) 0.0004(5) -0.0026(6) -0.0003(6) C1 0.0135(7) 0.0179(7) 0.0138(10) -0.0005(7) -0.0010(7) -0.0014(6) C2 0.0151(8) 0.0209(8) 0.0183(11) 0.0005(8) 0.0004(8) -0.0025(6) C3 0.0156(9) 0.0260(9) 0.0210(12) 0.0006(9) 0.0011(9) -0.0002(7) C4 0.0204(9) 0.0238(8) 0.0206(12) 0.0002(9) 0.0015(9) 0.0028(8) C5 0.0212(9) 0.0190(8) 0.0180(11) -0.0002(8) -0.0001(7) 0.0011(6) C6 0.0113(9) 0.0174(8) 0.0211(6) -0.0001(6) -0.0020(8) 0.0001(7) C7 0.0152(11) 0.0176(8) 0.0257(9) 0.0009(7) -0.0035(9) -0.0009(8) C8 0.0219(12) 0.0206(10) 0.0309(12) -0.0042(7) -0.0060(10) -0.0022(9) C9 0.0180(12) 0.0299(10) 0.0234(10) -0.0061(8) -0.0042(10) 0.0025(9) C10 0.0211(12) 0.0285(10) 0.0205(8) 0.0016(8) -0.0023(10) 0.0015(9) C11 0.0189(11) 0.0206(9) 0.0195(8) 0.0013(6) 0.0005(9) -0.0002(8) C12 0.0140(9) 0.0193(6) 0.0215(11) -0.0024(6) 0.0000(8) -0.0006(6) C13 0.0247(13) 0.0242(9) 0.0389(16) -0.0038(10) 0.0136(10) -0.0013(8) C14 0.0310(16) 0.0284(11) 0.055(2) -0.0085(12) 0.0197(13) 0.0026(10) C15 0.0287(14) 0.0225(10) 0.0441(18) -0.0075(10) 0.0040(11) 0.0047(9) C16 0.0267(13) 0.0201(8) 0.0298(14) -0.0004(9) -0.0016(9) 0.0025(9) C17 0.0194(11) 0.0202(7) 0.0211(12) -0.0002(8) 0.0009(8) 0.0015(7) C18 0.0115(9) 0.0170(6) 0.0131(9) -0.0003(6) -0.0013(6) -0.0020(6) C19 0.0210(12) 0.0153(8) 0.0252(12) 0.0033(7) -0.0084(9) -0.0013(7) C20 0.0182(11) 0.0166(8) 0.0221(11) 0.0031(7) -0.0062(8) -0.0004(7) C21 0.0131(7) 0.0148(9) 0.0207(7) 0.0014(7) -0.0049(5) -0.0016(7) C22 0.0131(7) 0.0177(9) 0.0255(8) 0.0009(8) -0.0041(6) -0.0012(7) C23 0.0128(8) 0.0277(12) 0.0291(9) 0.0013(10) -0.0048(7) -0.0012(9) C24 0.0181(8) 0.0295(12) 0.0265(9) 0.0027(10) -0.0087(9) -0.0025(9) C25 0.0203(8) 0.0260(11) 0.0200(9) 0.0015(9) -0.0055(7) -0.0042(9) C26 0.0169(7) 0.0183(9) 0.0208(8) 0.0009(8) -0.0042(6) -0.0027(7) C27 0.0154(11) 0.0275(10) 0.0273(9) -0.0015(9) -0.0013(7) 0.0002(8) C28 0.0248(14) 0.0284(10) 0.0395(17) -0.0037(10) 0.0080(12) 0.0018(9) C29 0.0313(15) 0.0326(11) 0.0284(13) 0.0038(11) 0.0026(11) -0.0033(10) C30 0.0182(8) 0.0246(9) 0.0243(11) -0.0026(8) -0.0013(7) -0.0022(9) C31 0.0233(13) 0.0337(11) 0.0299(14) 0.0023(10) 0.0038(10) -0.0042(11) C32 0.0246(13) 0.0261(9) 0.0467(19) -0.0060(10) 0.0039(13) 0.0001(9) C33 0.0145(7) 0.0189(9) 0.0123(9) -0.0006(6) -0.0026(6) -0.0009(6) C34 0.0208(7) 0.0213(10) 0.0154(10) -0.0017(7) 0.0055(7) -0.0030(7) C35 0.0307(9) 0.0267(12) 0.0175(12) -0.0062(8) 0.0012(9) -0.0039(9) C36 0.0291(9) 0.0299(12) 0.0163(12) -0.0031(8) -0.0060(9) -0.0075(9) C37 0.0175(9) 0.0300(12) 0.0187(12) -0.0001(8) -0.0057(8) -0.0051(8) C38 0.0143(7) 0.0223(9) 0.0148(10) 0.0003(7) -0.0031(7) -0.0003(7) C39 0.0234(8) 0.0303(11) 0.0436(17) -0.0139(11) 0.0139(11) -0.0043(9) C40 0.0275(13) 0.0330(11) 0.0422(18) -0.0045(12) 0.0124(13) 0.0035(10) C41 0.067(3) 0.0377(17) 0.129(4) 0.023(2) 0.073(3) 0.0054(18) C42 0.0151(9) 0.0258(10) 0.0226(12) -0.0017(7) -0.0007(8) 0.0016(7) C43 0.0184(11) 0.0335(13) 0.0290(14) -0.0041(10) 0.0044(8) -0.0011(9) C44 0.045(2) 0.0296(12) 0.047(2) 0.0080(11) 0.0142(15) 0.0137(12) Sb1 0.02033(9) 0.02198(8) 0.02117(9) 0.00110(6) 0.00284(6) 0.00531(6) F1 0.0191(7) 0.0691(12) 0.0440(11) 0.0063(10) 0.0076(6) -0.0011(7) F2 0.0748(14) 0.0370(7) 0.0474(12) 0.0026(8) 0.0197(10) 0.0319(8) F3 0.0357(7) 0.0287(7) 0.0415(10) 0.0105(7) 0.0127(7) -0.0031(6) F4 0.0345(9) 0.0198(6) 0.0391(10) 0.0016(6) 0.0075(7) 0.0026(5) F5 0.0496(11) 0.0603(12) 0.0248(7) 0.0026(7) -0.0093(7) 0.0087(9) F6 0.0457(11) 0.0409(9) 0.0236(6) 0.0015(6) -0.0046(7) -0.0131(8) O1 0.0398(13) 0.0235(9) 0.0590(17) -0.0065(9) -0.0076(12) -0.0049(8) C45 0.0291(11) 0.0228(9) 0.0236(13) -0.0015(9) -0.0038(10) -0.0008(8) C46 0.0359(14) 0.052(2) 0.057(3) -0.0113(18) 0.0022(16) -0.0160(12) C47 0.0486(17) 0.0416(15) 0.0376(19) -0.0091(14) -0.0019(15) 0.0156(14) _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 C18 1.913(2) . ? Cu1 N1 2.048(2) . ? Cu1 S1 2.2674(8) . ? S1 P1 1.9732(9) . ? P1 N2 1.668(2) . ? P1 C12 1.803(2) . ? P1 C6 1.809(3) . ? N1 C1 1.346(3) . ? N1 C5 1.368(3) . ? N2 C1 1.398(3) . ? N2 H2N 0.8800 . ? N3 C18 1.363(3) . ? N3 C19 1.389(3) . ? N3 C21 1.443(3) . ? N4 C18 1.363(3) . ? N4 C20 1.385(3) . ? N4 C33 1.448(3) . ? C1 C2 1.399(3) . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.399(4) . ? C3 H3 0.9500 . ? C4 C5 1.367(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.400(3) . ? C6 C11 1.400(3) . ? C7 C8 1.394(4) . ? C7 H7 0.9500 . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 C11 1.394(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.391(4) . ? C12 C17 1.397(4) . ? C13 C14 1.396(4) . ? C13 H13 0.9500 . ? C14 C15 1.388(5) . ? C14 H14 0.9500 . ? C15 C16 1.369(4) . ? C15 H15 0.9500 . ? C16 C17 1.397(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.344(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.396(4) . ? C21 C22 1.406(4) . ? C22 C23 1.401(3) . ? C22 C27 1.516(4) . ? C23 C24 1.388(4) . ? C23 H23 0.9500 . ? C24 C25 1.385(4) . ? C24 H24 0.9500 . ? C25 C26 1.399(3) . ? C25 H25 0.9500 . ? C26 C30 1.516(4) . ? C27 C28 1.530(4) . ? C27 C29 1.533(4) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C32 1.531(4) . ? C30 C31 1.536(4) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C38 1.392(3) . ? C33 C34 1.410(3) . ? C34 C35 1.398(3) . ? C34 C39 1.510(4) . ? C35 C36 1.377(4) . ? C35 H35 0.9500 . ? C36 C37 1.373(4) . ? C36 H36 0.9500 . ? C37 C38 1.401(3) . ? C37 H37 0.9500 . ? C38 C42 1.515(4) . ? C39 C40 1.519(4) . ? C39 C41 1.528(5) . ? C39 H39 1.0000 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.528(4) . ? C42 C44 1.535(4) . ? C42 H42 1.0000 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? Sb1 F2 1.8604(19) . ? Sb1 F1 1.866(2) . ? Sb1 F6 1.8667(18) . ? Sb1 F5 1.872(2) . ? Sb1 F4 1.8756(16) . ? Sb1 F3 1.8780(18) . ? O1 C45 1.205(3) . ? C45 C46 1.476(5) . ? C45 C47 1.488(4) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? 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 C18 Cu1 N1 129.15(9) . . ? C18 Cu1 S1 121.60(8) . . ? N1 Cu1 S1 108.84(6) . . ? P1 S1 Cu1 92.60(3) . . ? N2 P1 C12 102.53(11) . . ? N2 P1 C6 105.19(11) . . ? C12 P1 C6 108.81(11) . . ? N2 P1 S1 117.00(8) . . ? C12 P1 S1 110.01(9) . . ? C6 P1 S1 112.59(9) . . ? C1 N1 C5 116.9(2) . . ? C1 N1 Cu1 126.84(17) . . ? C5 N1 Cu1 112.93(16) . . ? C1 N2 P1 126.51(16) . . ? C1 N2 H2N 116.7 . . ? P1 N2 H2N 116.7 . . ? C18 N3 C19 111.85(19) . . ? C18 N3 C21 124.87(19) . . ? C19 N3 C21 122.50(19) . . ? C18 N4 C20 111.87(19) . . ? C18 N4 C33 124.54(19) . . ? C20 N4 C33 123.16(19) . . ? N1 C1 N2 118.8(2) . . ? N1 C1 C2 122.7(2) . . ? N2 C1 C2 118.4(2) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 N1 123.6(2) . . ? C4 C5 H5 118.2 . . ? N1 C5 H5 118.2 . . ? C7 C6 C11 119.4(2) . . ? C7 C6 P1 121.8(2) . . ? C11 C6 P1 118.79(18) . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 119.5(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C6 120.4(2) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C17 119.2(2) . . ? C13 C12 P1 118.5(2) . . ? C17 C12 P1 122.3(2) . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.7(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 119.8(3) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? N4 C18 N3 103.13(19) . . ? N4 C18 Cu1 128.25(16) . . ? N3 C18 Cu1 128.53(17) . . ? C20 C19 N3 106.4(2) . . ? C20 C19 H19 126.8 . . ? N3 C19 H19 126.8 . . ? C19 C20 N4 106.7(2) . . ? C19 C20 H20 126.6 . . ? N4 C20 H20 126.6 . . ? C26 C21 C22 123.6(2) . . ? C26 C21 N3 119.6(2) . . ? C22 C21 N3 116.7(2) . . ? C23 C22 C21 116.8(3) . . ? C23 C22 C27 119.7(2) . . ? C21 C22 C27 123.5(2) . . ? C24 C23 C22 121.0(3) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C25 C24 C23 120.3(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 121.3(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C21 C26 C25 116.9(2) . . ? C21 C26 C30 123.1(2) . . ? C25 C26 C30 120.0(2) . . ? C22 C27 C28 111.4(2) . . ? C22 C27 C29 111.7(2) . . ? C28 C27 C29 110.5(2) . . ? C22 C27 H27 107.7 . . ? C28 C27 H27 107.7 . . ? C29 C27 H27 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 C32 111.4(2) . . ? C26 C30 C31 111.1(2) . . ? C32 C30 C31 110.6(3) . . ? C26 C30 H30 107.9 . . ? C32 C30 H30 107.9 . . ? C31 C30 H30 107.9 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C38 C33 C34 124.2(2) . . ? C38 C33 N4 118.3(2) . . ? C34 C33 N4 117.5(2) . . ? C35 C34 C33 115.8(2) . . ? C35 C34 C39 121.5(2) . . ? C33 C34 C39 122.6(2) . . ? C36 C35 C34 121.6(3) . . ? C36 C35 H35 119.2 . . ? C34 C35 H35 119.2 . . ? C37 C36 C35 120.7(2) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C38 121.3(3) . . ? C36 C37 H37 119.4 . . ? C38 C37 H37 119.4 . . ? C33 C38 C37 116.4(2) . . ? C33 C38 C42 123.0(2) . . ? C37 C38 C42 120.6(2) . . ? C34 C39 C40 114.0(2) . . ? C34 C39 C41 109.7(3) . . ? C40 C39 C41 109.2(3) . . ? C34 C39 H39 107.9 . . ? C40 C39 H39 107.9 . . ? C41 C39 H39 107.9 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C38 C42 C43 112.4(2) . . ? C38 C42 C44 110.7(2) . . ? C43 C42 C44 109.8(2) . . ? C38 C42 H42 107.9 . . ? C43 C42 H42 107.9 . . ? C44 C42 H42 107.9 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? F2 Sb1 F1 91.55(11) . . ? F2 Sb1 F6 90.62(10) . . ? F1 Sb1 F6 90.71(9) . . ? F2 Sb1 F5 89.90(10) . . ? F1 Sb1 F5 91.33(10) . . ? F6 Sb1 F5 177.89(10) . . ? F2 Sb1 F4 178.92(10) . . ? F1 Sb1 F4 89.46(9) . . ? F6 Sb1 F4 89.76(9) . . ? F5 Sb1 F4 89.68(9) . . ? F2 Sb1 F3 89.71(10) . . ? F1 Sb1 F3 178.67(9) . . ? F6 Sb1 F3 88.86(9) . . ? F5 Sb1 F3 89.09(10) . . ? F4 Sb1 F3 89.28(8) . . ? O1 C45 C46 122.6(3) . . ? O1 C45 C47 121.4(3) . . ? C46 C45 C47 116.1(3) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? 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 C18 Cu1 S1 P1 169.83(8) . . . . ? N1 Cu1 S1 P1 -16.86(7) . . . . ? Cu1 S1 P1 N2 50.11(9) . . . . ? Cu1 S1 P1 C12 166.51(9) . . . . ? Cu1 S1 P1 C6 -71.94(9) . . . . ? C18 Cu1 N1 C1 153.80(18) . . . . ? S1 Cu1 N1 C1 -18.9(2) . . . . ? C18 Cu1 N1 C5 -4.7(2) . . . . ? S1 Cu1 N1 C5 -177.40(15) . . . . ? C12 P1 N2 C1 173.8(2) . . . . ? C6 P1 N2 C1 60.1(2) . . . . ? S1 P1 N2 C1 -65.7(2) . . . . ? C5 N1 C1 N2 -179.2(2) . . . . ? Cu1 N1 C1 N2 23.0(3) . . . . ? C5 N1 C1 C2 2.2(3) . . . . ? Cu1 N1 C1 C2 -155.63(19) . . . . ? P1 N2 C1 N1 18.9(3) . . . . ? P1 N2 C1 C2 -162.35(19) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? N2 C1 C2 C3 -179.6(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C3 C4 C5 N1 0.9(4) . . . . ? C1 N1 C5 C4 -2.2(4) . . . . ? Cu1 N1 C5 C4 158.6(2) . . . . ? N2 P1 C6 C7 -116.3(2) . . . . ? C12 P1 C6 C7 134.4(2) . . . . ? S1 P1 C6 C7 12.2(2) . . . . ? N2 P1 C6 C11 65.3(2) . . . . ? C12 P1 C6 C11 -44.0(2) . . . . ? S1 P1 C6 C11 -166.24(18) . . . . ? C11 C6 C7 C8 -1.4(4) . . . . ? P1 C6 C7 C8 -179.8(2) . . . . ? C6 C7 C8 C9 1.0(4) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C9 C10 C11 C6 -0.7(4) . . . . ? C7 C6 C11 C10 1.3(4) . . . . ? P1 C6 C11 C10 179.8(2) . . . . ? N2 P1 C12 C13 144.8(2) . . . . ? C6 P1 C12 C13 -104.1(2) . . . . ? S1 P1 C12 C13 19.7(2) . . . . ? N2 P1 C12 C17 -36.7(2) . . . . ? C6 P1 C12 C17 74.3(2) . . . . ? S1 P1 C12 C17 -161.90(19) . . . . ? C17 C12 C13 C14 -0.5(4) . . . . ? P1 C12 C13 C14 178.0(3) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C13 C14 C15 C16 0.6(5) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C15 C16 C17 C12 -0.8(4) . . . . ? C13 C12 C17 C16 1.0(4) . . . . ? P1 C12 C17 C16 -177.4(2) . . . . ? C20 N4 C18 N3 0.9(3) . . . . ? C33 N4 C18 N3 173.5(2) . . . . ? C20 N4 C18 Cu1 -175.98(19) . . . . ? C33 N4 C18 Cu1 -3.3(4) . . . . ? C19 N3 C18 N4 -0.8(3) . . . . ? C21 N3 C18 N4 -170.9(2) . . . . ? C19 N3 C18 Cu1 176.0(2) . . . . ? C21 N3 C18 Cu1 5.9(4) . . . . ? N1 Cu1 C18 N4 -79.5(2) . . . . ? S1 Cu1 C18 N4 92.3(2) . . . . ? N1 Cu1 C18 N3 104.4(2) . . . . ? S1 Cu1 C18 N3 -83.7(2) . . . . ? C18 N3 C19 C20 0.5(3) . . . . ? C21 N3 C19 C20 170.9(2) . . . . ? N3 C19 C20 N4 0.0(3) . . . . ? C18 N4 C20 C19 -0.6(3) . . . . ? C33 N4 C20 C19 -173.3(2) . . . . ? C18 N3 C21 C26 -87.3(3) . . . . ? C19 N3 C21 C26 103.7(3) . . . . ? C18 N3 C21 C22 95.7(3) . . . . ? C19 N3 C21 C22 -73.4(3) . . . . ? C26 C21 C22 C23 -0.3(4) . . . . ? N3 C21 C22 C23 176.6(2) . . . . ? C26 C21 C22 C27 -179.5(2) . . . . ? N3 C21 C22 C27 -2.5(3) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C27 C22 C23 C24 179.5(2) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C23 C24 C25 C26 -0.2(4) . . . . ? C22 C21 C26 C25 0.1(4) . . . . ? N3 C21 C26 C25 -176.7(2) . . . . ? C22 C21 C26 C30 178.6(2) . . . . ? N3 C21 C26 C30 1.7(3) . . . . ? C24 C25 C26 C21 0.1(4) . . . . ? C24 C25 C26 C30 -178.4(2) . . . . ? C23 C22 C27 C28 62.1(3) . . . . ? C21 C22 C27 C28 -118.7(3) . . . . ? C23 C22 C27 C29 -61.9(3) . . . . ? C21 C22 C27 C29 117.2(3) . . . . ? C21 C26 C30 C32 -112.9(3) . . . . ? C25 C26 C30 C32 65.5(3) . . . . ? C21 C26 C30 C31 123.3(3) . . . . ? C25 C26 C30 C31 -58.3(3) . . . . ? C18 N4 C33 C38 101.6(3) . . . . ? C20 N4 C33 C38 -86.6(3) . . . . ? C18 N4 C33 C34 -81.1(3) . . . . ? C20 N4 C33 C34 90.7(3) . . . . ? C38 C33 C34 C35 -1.7(4) . . . . ? N4 C33 C34 C35 -178.8(2) . . . . ? C38 C33 C34 C39 176.2(3) . . . . ? N4 C33 C34 C39 -0.9(4) . . . . ? C33 C34 C35 C36 1.0(4) . . . . ? C39 C34 C35 C36 -176.9(3) . . . . ? C34 C35 C36 C37 0.8(4) . . . . ? C35 C36 C37 C38 -2.2(4) . . . . ? C34 C33 C38 C37 0.4(4) . . . . ? N4 C33 C38 C37 177.5(2) . . . . ? C34 C33 C38 C42 -179.0(2) . . . . ? N4 C33 C38 C42 -1.9(4) . . . . ? C36 C37 C38 C33 1.6(4) . . . . ? C36 C37 C38 C42 -179.0(2) . . . . ? C35 C34 C39 C40 -38.3(4) . . . . ? C33 C34 C39 C40 143.9(3) . . . . ? C35 C34 C39 C41 84.5(4) . . . . ? C33 C34 C39 C41 -93.3(4) . . . . ? C33 C38 C42 C43 -141.7(2) . . . . ? C37 C38 C42 C43 38.9(3) . . . . ? C33 C38 C42 C44 95.1(3) . . . . ? C37 C38 C42 C44 -84.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O1 0.88 2.05 2.875(3) 155.5 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.986 _refine_diff_density_min -1.220 _refine_diff_density_rms 0.100 #===END # 1529 [Cu(NHC)(SPN-iPr)]SbF6 data_7b-1529 _database_code_depnum_ccdc_archive 'CCDC 810372' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_ #5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1529 (Cu(NHC)(SPN-iPr))SbF6 at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C38 H55 Cu N4 P S, F6 Sb' _chemical_formula_sum 'C38 H55 Cu F6 N4 P S Sb' _chemical_formula_weight 930.18 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.1074(2) _cell_length_b 12.8043(2) _cell_length_c 35.3387(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.9200(10) _cell_angle_gamma 90.00 _cell_volume 4099.00(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9860 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 30.15 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 1.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.63 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Bruker Kappa APEX-2 CCD diffractometer. Isopropyl group C9-C10-C11 is orientatien disordered and adopts two discernible orientations. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 55780 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.00 _reflns_number_total 11931 _reflns_number_gt 11075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0159P)^2^+4.9316P] 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 11931 _refine_ls_number_parameters 495 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.199 _refine_ls_shift/su_max 0.004 _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 0.17331(2) 0.292506(16) 0.373659(6) 0.01453(5) Uani 1 1 d U . . S1 S 0.29482(6) 0.36722(4) 0.427426(13) 0.02184(10) Uani 1 1 d U A . P1 P 0.31321(5) 0.50567(3) 0.403756(12) 0.01417(8) Uani 1 1 d DU . . N1 N 0.21474(17) 0.38433(12) 0.32867(4) 0.0158(3) Uani 1 1 d U A . N2 N 0.38034(18) 0.50232(13) 0.36149(4) 0.0188(3) Uani 1 1 d U A . H2N H 0.4638 0.5363 0.3604 0.023 Uiso 1 1 calc R . . N3 N -0.02065(16) 0.10540(11) 0.35453(4) 0.0144(3) Uani 1 1 d U . . N4 N 0.07327(16) 0.10531(11) 0.41236(4) 0.0144(3) Uani 1 1 d U . . C1 C 0.32432(19) 0.45411(13) 0.32790(5) 0.0144(3) Uani 1 1 d U . . C2 C 0.3850(2) 0.48153(14) 0.29435(5) 0.0178(3) Uani 1 1 d U A . H2 H 0.4647 0.5296 0.2950 0.021 Uiso 1 1 calc R . . C3 C 0.3270(2) 0.43761(15) 0.26061(5) 0.0203(3) Uani 1 1 d U . . H3 H 0.3673 0.4540 0.2376 0.024 Uiso 1 1 calc R A . C4 C 0.2088(2) 0.36895(15) 0.26054(5) 0.0210(3) Uani 1 1 d U A . H4 H 0.1651 0.3390 0.2375 0.025 Uiso 1 1 calc R . . C5 C 0.1565(2) 0.34541(14) 0.29463(5) 0.0194(3) Uani 1 1 d U . . H5 H 0.0748 0.2992 0.2944 0.023 Uiso 1 1 calc R A . C6 C 0.4507(2) 0.58732(14) 0.43088(5) 0.0188(3) Uani 1 1 d DU A . H6 H 0.4593 0.6544 0.4168 0.023 Uiso 1 1 calc R . . C7 C 0.6019(2) 0.53392(17) 0.43508(6) 0.0257(4) Uani 1 1 d DU . . H7A H 0.6727 0.5775 0.4508 0.039 Uiso 1 1 calc R A . H7B H 0.6359 0.5244 0.4099 0.039 Uiso 1 1 calc R . . H7C H 0.5939 0.4657 0.4473 0.039 Uiso 1 1 calc R . . C8 C 0.3996(3) 0.61222(17) 0.46991(6) 0.0283(4) Uani 1 1 d DU . . H8A H 0.3749 0.5471 0.4824 0.042 Uiso 1 1 calc R A . H8B H 0.3123 0.6573 0.4666 0.042 Uiso 1 1 calc R . . H8C H 0.4790 0.6481 0.4857 0.042 Uiso 1 1 calc R . . C9 C 0.1334(4) 0.5722(3) 0.39133(11) 0.0209(7) Uani 0.600(4) 1 d PDU A 1 H9 H 0.0848 0.5364 0.3682 0.025 Uiso 0.600(4) 1 calc PR A 1 C10 C 0.1552(9) 0.6869(4) 0.3802(2) 0.0311(16) Uani 0.600(4) 1 d PDU A 1 H10A H 0.0648 0.7130 0.3658 0.047 Uiso 0.600(4) 1 calc PR A 1 H10B H 0.2374 0.6919 0.3644 0.047 Uiso 0.600(4) 1 calc PR A 1 H10C H 0.1774 0.7290 0.4032 0.047 Uiso 0.600(4) 1 calc PR A 1 C11 C 0.0271(4) 0.5644(3) 0.42176(12) 0.0337(9) Uani 0.600(4) 1 d PDU A 1 H11A H -0.0232 0.6315 0.4239 0.040 Uiso 0.600(4) 1 calc PR A 1 H11B H 0.0821 0.5469 0.4462 0.040 Uiso 0.600(4) 1 calc PR A 1 H11C H -0.0462 0.5099 0.4147 0.040 Uiso 0.600(4) 1 calc PR A 1 C9' C 0.1441(6) 0.5795(5) 0.40567(17) 0.0209(7) Uani 0.40 1 d PDU A 2 H9' H 0.1242 0.5839 0.4329 0.025 Uiso 0.400(4) 1 calc PR A 2 C10' C 0.1563(14) 0.6911(7) 0.3909(4) 0.0311(16) Uani 0.40 1 d PDU A 2 H10D H 0.0665 0.7300 0.3949 0.047 Uiso 0.400(4) 1 calc PR A 2 H10E H 0.1683 0.6894 0.3637 0.047 Uiso 0.400(4) 1 calc PR A 2 H10F H 0.2420 0.7255 0.4046 0.047 Uiso 0.400(4) 1 calc PR A 2 C11' C 0.0127(5) 0.5238(4) 0.38373(15) 0.0250(10) Uani 0.400(4) 1 d PDU A 2 H11D H -0.0782 0.5420 0.3949 0.030 Uiso 0.400(4) 1 calc PR A 2 H11E H 0.0279 0.4481 0.3853 0.030 Uiso 0.400(4) 1 calc PR A 2 H11F H 0.0043 0.5457 0.3570 0.030 Uiso 0.400(4) 1 calc PR A 2 C12 C 0.07271(19) 0.16128(13) 0.37945(5) 0.0133(3) Uani 1 1 d U . . C13 C -0.0788(2) 0.01929(14) 0.37149(6) 0.0200(3) Uani 1 1 d U . . H13 H -0.1474 -0.0297 0.3597 0.024 Uiso 1 1 calc R . . C14 C -0.0189(2) 0.01873(15) 0.40796(5) 0.0198(3) Uani 1 1 d U . . H14 H -0.0363 -0.0310 0.4269 0.024 Uiso 1 1 calc R . . C15 C -0.0617(2) 0.13093(14) 0.31514(5) 0.0165(3) Uani 1 1 d U . . C16 C -0.1913(2) 0.18837(14) 0.30610(5) 0.0199(3) Uani 1 1 d U . . C17 C -0.2316(3) 0.20956(17) 0.26759(6) 0.0291(4) Uani 1 1 d U . . H17 H -0.3188 0.2484 0.2603 0.035 Uiso 1 1 calc R . . C18 C -0.1460(3) 0.17478(17) 0.24019(6) 0.0330(5) Uani 1 1 d U . . H18 H -0.1761 0.1890 0.2142 0.040 Uiso 1 1 calc R . . C19 C -0.0174(3) 0.11966(17) 0.24987(6) 0.0304(4) Uani 1 1 d U . . H19 H 0.0404 0.0977 0.2304 0.036 Uiso 1 1 calc R . . C20 C 0.0292(2) 0.09558(15) 0.28790(5) 0.0215(3) Uani 1 1 d U . . C21 C -0.2816(2) 0.23081(16) 0.33631(6) 0.0255(4) Uani 1 1 d U . . H21 H -0.2443 0.1978 0.3611 0.031 Uiso 1 1 calc R . . C22 C -0.2582(3) 0.34896(19) 0.34030(9) 0.0449(7) Uani 1 1 d U . . H22A H -0.1531 0.3636 0.3469 0.067 Uiso 1 1 calc R . . H22B H -0.3147 0.3757 0.3604 0.067 Uiso 1 1 calc R . . H22C H -0.2920 0.3832 0.3162 0.067 Uiso 1 1 calc R . . C23 C -0.4462(3) 0.2050(2) 0.32843(8) 0.0402(6) Uani 1 1 d U . . H23A H -0.4862 0.2381 0.3046 0.060 Uiso 1 1 calc R . . H23B H -0.4987 0.2312 0.3493 0.060 Uiso 1 1 calc R . . H23C H -0.4589 0.1291 0.3264 0.060 Uiso 1 1 calc R . . C24 C 0.1724(2) 0.03730(17) 0.29926(6) 0.0276(4) Uani 1 1 d U . . H24 H 0.2185 0.0684 0.3236 0.033 Uiso 1 1 calc R . . C25 C 0.2838(3) 0.0472(2) 0.26974(8) 0.0475(7) Uani 1 1 d U . . H25A H 0.2466 0.0098 0.2465 0.071 Uiso 1 1 calc R . . H25B H 0.3785 0.0171 0.2800 0.071 Uiso 1 1 calc R . . H25C H 0.2974 0.1211 0.2638 0.071 Uiso 1 1 calc R . . C26 C 0.1451(3) -0.07861(19) 0.30648(9) 0.0398(6) Uani 1 1 d U . . H26A H 0.0750 -0.0857 0.3256 0.060 Uiso 1 1 calc R . . H26B H 0.2385 -0.1124 0.3157 0.060 Uiso 1 1 calc R . . H26C H 0.1042 -0.1119 0.2827 0.060 Uiso 1 1 calc R . . C27 C 0.15870(19) 0.12910(13) 0.44799(5) 0.0138(3) Uani 1 1 d U . . C28 C 0.0837(2) 0.16854(15) 0.47751(5) 0.0192(3) Uani 1 1 d U . . C29 C 0.1662(2) 0.18622(15) 0.51255(5) 0.0203(3) Uani 1 1 d U . . H29 H 0.1191 0.2139 0.5331 0.024 Uiso 1 1 calc R . . C30 C 0.3152(2) 0.16392(15) 0.51765(5) 0.0202(3) Uani 1 1 d U . . H30 H 0.3693 0.1751 0.5418 0.024 Uiso 1 1 calc R . . C31 C 0.3865(2) 0.12508(15) 0.48764(5) 0.0178(3) Uani 1 1 d U . . H31 H 0.4892 0.1104 0.4916 0.021 Uiso 1 1 calc R . . C32 C 0.31045(19) 0.10717(13) 0.45195(5) 0.0148(3) Uani 1 1 d U . . C33 C -0.0792(2) 0.1952(2) 0.47192(6) 0.0306(5) Uani 1 1 d U . . H33 H -0.1218 0.1614 0.4477 0.037 Uiso 1 1 calc R . . C34 C -0.1001(4) 0.3121(3) 0.46732(11) 0.0723(13) Uani 1 1 d U . . H34A H -0.0556 0.3476 0.4903 0.108 Uiso 1 1 calc R . . H34B H -0.2058 0.3282 0.4635 0.108 Uiso 1 1 calc R . . H34C H -0.0524 0.3360 0.4452 0.108 Uiso 1 1 calc R . . C35 C -0.1625(2) 0.15326(17) 0.50382(6) 0.0252(4) Uani 1 1 d U . . H35A H -0.1222 0.1844 0.5280 0.038 Uiso 1 1 calc R . . H35B H -0.1515 0.0772 0.5052 0.038 Uiso 1 1 calc R . . H35C H -0.2673 0.1711 0.4988 0.038 Uiso 1 1 calc R . . C36 C 0.3868(2) 0.06405(15) 0.41894(5) 0.0189(3) Uani 1 1 d U . . H36 H 0.3434 0.1002 0.3953 0.023 Uiso 1 1 calc R . . C37 C 0.5534(2) 0.08466(18) 0.42293(6) 0.0254(4) Uani 1 1 d U . . H37A H 0.5717 0.1594 0.4272 0.038 Uiso 1 1 calc R . . H37B H 0.5944 0.0629 0.3996 0.038 Uiso 1 1 calc R . . H37C H 0.6007 0.0449 0.4445 0.038 Uiso 1 1 calc R . . C38 C 0.3567(2) -0.05293(17) 0.41364(6) 0.0258(4) Uani 1 1 d U . . H38A H 0.3963 -0.0905 0.4366 0.039 Uiso 1 1 calc R . . H38B H 0.4046 -0.0784 0.3918 0.039 Uiso 1 1 calc R . . H38C H 0.2501 -0.0648 0.4091 0.039 Uiso 1 1 calc R . . Sb1 Sb 0.651258(15) 0.755725(10) 0.339328(3) 0.02046(4) Uani 1 1 d U . . F1 F 0.66442(15) 0.61036(10) 0.34705(4) 0.0307(3) Uani 1 1 d U . . F2 F 0.63245(19) 0.90033(11) 0.33194(4) 0.0416(4) Uani 1 1 d U . . F3 F 0.84149(15) 0.75898(15) 0.32454(4) 0.0464(4) Uani 1 1 d U . . F4 F 0.46106(16) 0.74965(11) 0.35475(4) 0.0385(3) Uani 1 1 d U . . F5 F 0.57138(15) 0.73286(11) 0.28921(4) 0.0323(3) Uani 1 1 d U . . F6 F 0.7291(2) 0.77728(12) 0.38980(4) 0.0458(4) Uani 1 1 d U . . 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 0.01750(10) 0.01147(9) 0.01459(10) 0.00046(7) 0.00153(8) -0.00353(7) S1 0.0360(3) 0.01471(19) 0.01394(19) 0.00192(15) -0.00179(18) -0.00801(18) P1 0.0174(2) 0.01262(18) 0.01276(18) 0.00039(15) 0.00281(15) -0.00255(15) N1 0.0196(7) 0.0136(6) 0.0139(6) 0.0004(5) 0.0009(5) -0.0034(5) N2 0.0207(7) 0.0231(7) 0.0131(6) -0.0024(5) 0.0034(5) -0.0107(6) N3 0.0144(7) 0.0122(6) 0.0159(6) 0.0015(5) -0.0014(5) -0.0019(5) N4 0.0125(6) 0.0147(6) 0.0155(6) 0.0034(5) -0.0004(5) -0.0025(5) C1 0.0171(8) 0.0134(7) 0.0126(6) -0.0001(5) 0.0013(6) -0.0014(6) C2 0.0199(8) 0.0183(8) 0.0154(7) 0.0011(6) 0.0036(6) -0.0031(6) C3 0.0253(9) 0.0219(9) 0.0142(7) 0.0002(6) 0.0051(7) -0.0002(7) C4 0.0283(9) 0.0196(8) 0.0147(7) -0.0032(6) 0.0001(7) -0.0026(7) C5 0.0246(9) 0.0164(8) 0.0166(7) -0.0012(6) -0.0011(6) -0.0047(6) C6 0.0259(8) 0.0158(7) 0.0144(7) -0.0017(6) -0.0001(6) -0.0061(6) C7 0.0235(8) 0.0311(10) 0.0212(9) -0.0001(8) -0.0038(7) -0.0044(7) C8 0.0438(12) 0.0246(10) 0.0167(8) -0.0065(7) 0.0044(8) -0.0048(9) C9 0.0186(9) 0.0179(11) 0.026(2) -0.0021(15) 0.0039(10) -0.0017(7) C10 0.0226(11) 0.0212(10) 0.049(5) 0.0096(18) 0.001(2) 0.0026(8) C11 0.0257(16) 0.0315(19) 0.046(2) 0.0023(16) 0.0167(15) 0.0016(14) C9' 0.0186(9) 0.0179(11) 0.026(2) -0.0021(15) 0.0039(10) -0.0017(7) C10' 0.0226(11) 0.0212(10) 0.049(5) 0.0096(18) 0.001(2) 0.0026(8) C11' 0.0181(16) 0.028(2) 0.028(2) -0.0003(19) 0.0001(17) -0.0016(15) C12 0.0139(7) 0.0125(7) 0.0134(6) 0.0006(5) 0.0006(5) 0.0001(5) C13 0.0181(8) 0.0162(8) 0.0247(8) 0.0054(6) -0.0025(7) -0.0059(6) C14 0.0164(8) 0.0191(8) 0.0232(8) 0.0078(6) -0.0011(6) -0.0059(6) C15 0.0201(8) 0.0131(7) 0.0156(7) -0.0006(6) -0.0019(6) -0.0053(6) C16 0.0229(8) 0.0143(8) 0.0207(8) 0.0023(6) -0.0053(6) -0.0039(6) C17 0.0371(11) 0.0216(9) 0.0253(8) 0.0059(7) -0.0128(7) -0.0054(8) C18 0.0572(14) 0.0233(10) 0.0158(8) 0.0025(7) -0.0093(8) -0.0135(9) C19 0.0487(12) 0.0238(10) 0.0189(8) -0.0056(7) 0.0043(8) -0.0131(8) C20 0.0286(9) 0.0157(8) 0.0204(8) -0.0050(6) 0.0034(6) -0.0075(6) C21 0.0203(8) 0.0220(9) 0.0334(10) 0.0041(8) -0.0002(7) 0.0045(7) C22 0.0442(14) 0.0239(10) 0.0694(19) -0.0089(11) 0.0197(13) 0.0039(9) C23 0.0218(9) 0.0461(14) 0.0515(15) 0.0168(12) -0.0019(9) 0.0005(9) C24 0.0251(9) 0.0260(9) 0.0325(10) -0.0115(8) 0.0073(7) -0.0029(7) C25 0.0383(13) 0.0563(16) 0.0517(16) -0.0223(13) 0.0233(12) -0.0085(12) C26 0.0321(12) 0.0246(9) 0.0624(17) -0.0056(10) 0.0027(11) 0.0057(8) C27 0.0134(7) 0.0142(7) 0.0136(6) 0.0037(5) 0.0003(5) -0.0006(5) C28 0.0176(7) 0.0240(9) 0.0164(7) 0.0045(6) 0.0030(6) 0.0042(6) C29 0.0222(8) 0.0227(9) 0.0163(7) 0.0004(7) 0.0035(6) 0.0035(7) C30 0.0213(8) 0.0213(9) 0.0175(8) -0.0002(7) -0.0007(6) -0.0006(7) C31 0.0138(7) 0.0211(8) 0.0180(7) 0.0008(6) -0.0009(6) -0.0013(6) C32 0.0132(7) 0.0127(7) 0.0183(7) 0.0019(6) 0.0013(5) -0.0007(6) C33 0.0193(8) 0.0543(13) 0.0189(9) 0.0054(9) 0.0045(7) 0.0128(9) C34 0.0476(17) 0.0722(18) 0.106(3) 0.069(2) 0.0502(18) 0.0422(15) C35 0.0187(9) 0.0292(10) 0.0282(10) -0.0008(8) 0.0049(7) 0.0004(7) C36 0.0145(7) 0.0249(8) 0.0174(7) 0.0007(7) 0.0027(6) 0.0025(6) C37 0.0149(8) 0.0346(11) 0.0276(10) 0.0019(8) 0.0060(7) 0.0011(7) C38 0.0222(9) 0.0250(9) 0.0296(10) -0.0089(8) -0.0005(8) 0.0042(7) Sb1 0.02527(7) 0.02149(6) 0.01436(6) 0.00144(4) 0.00077(4) -0.01181(5) F1 0.0331(7) 0.0221(5) 0.0370(7) 0.0020(5) 0.0030(5) -0.0013(5) F2 0.0625(10) 0.0230(6) 0.0355(7) 0.0070(5) -0.0127(7) -0.0194(6) F3 0.0210(6) 0.0820(12) 0.0353(7) 0.0236(8) -0.0013(5) -0.0172(6) F4 0.0371(7) 0.0346(7) 0.0475(8) 0.0062(6) 0.0224(6) 0.0017(6) F5 0.0319(7) 0.0425(8) 0.0204(5) -0.0051(5) -0.0064(5) -0.0075(6) F6 0.0771(11) 0.0407(8) 0.0166(6) 0.0009(5) -0.0099(6) -0.0134(8) _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 C12 1.9347(17) . ? Cu1 N1 2.0436(15) . ? Cu1 S1 2.3057(5) . ? S1 P1 1.9746(6) . ? P1 N2 1.6717(15) . ? P1 C9' 1.815(6) . ? P1 C6 1.8253(19) . ? P1 C9 1.858(4) . ? N1 C1 1.342(2) . ? N1 C5 1.358(2) . ? N2 C1 1.388(2) . ? N2 H2N 0.8800 . ? N3 C12 1.363(2) . ? N3 C13 1.386(2) . ? N3 C15 1.441(2) . ? N4 C12 1.366(2) . ? N4 C14 1.390(2) . ? N4 C27 1.443(2) . ? C1 C2 1.404(2) . ? C2 C3 1.374(3) . ? C2 H2 0.9500 . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.373(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.531(3) . ? C6 C8 1.534(3) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.523(5) . ? C9 C10 1.539(6) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C9' C10' 1.529(9) . ? C9' C11' 1.533(7) . ? C9' H9' 1.0000 . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? C13 C14 1.347(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.400(3) . ? C15 C20 1.408(3) . ? C16 C17 1.399(3) . ? C16 C21 1.514(3) . ? C17 C18 1.378(4) . ? C17 H17 0.9500 . ? C18 C19 1.380(4) . ? C18 H18 0.9500 . ? C19 C20 1.401(3) . ? C19 H19 0.9500 . ? C20 C24 1.520(3) . ? C21 C22 1.532(3) . ? C21 C23 1.532(3) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.531(3) . ? C24 C25 1.533(3) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.399(2) . ? C27 C32 1.403(2) . ? C28 C29 1.399(3) . ? C28 C33 1.516(3) . ? C29 C30 1.380(3) . ? C29 H29 0.9500 . ? C30 C31 1.391(3) . ? C30 H30 0.9500 . ? C31 C32 1.394(2) . ? C31 H31 0.9500 . ? C32 C36 1.522(2) . ? C33 C34 1.515(4) . ? C33 C35 1.520(3) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C38 1.531(3) . ? C36 C37 1.532(3) . ? C36 H36 1.0000 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? Sb1 F3 1.8609(14) . ? Sb1 F5 1.8672(12) . ? Sb1 F6 1.8704(13) . ? Sb1 F4 1.8704(14) . ? Sb1 F2 1.8752(14) . ? Sb1 F1 1.8832(13) . ? 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 C12 Cu1 N1 135.19(7) . . ? C12 Cu1 S1 117.74(5) . . ? N1 Cu1 S1 106.91(4) . . ? P1 S1 Cu1 94.47(2) . . ? N2 P1 C9' 115.9(2) . . ? N2 P1 C6 100.92(8) . . ? C9' P1 C6 102.8(2) . . ? N2 P1 C9 101.26(13) . . ? C6 P1 C9 113.67(14) . . ? N2 P1 S1 114.22(6) . . ? C9' P1 S1 110.0(2) . . ? C6 P1 S1 112.05(6) . . ? C9 P1 S1 113.62(13) . . ? C1 N1 C5 116.71(15) . . ? C1 N1 Cu1 126.60(12) . . ? C5 N1 Cu1 113.04(12) . . ? C1 N2 P1 129.76(13) . . ? C1 N2 H2N 115.1 . . ? P1 N2 H2N 115.1 . . ? C12 N3 C13 112.26(15) . . ? C12 N3 C15 125.99(14) . . ? C13 N3 C15 121.72(15) . . ? C12 N4 C14 111.98(15) . . ? C12 N4 C27 125.92(14) . . ? C14 N4 C27 122.09(14) . . ? N1 C1 N2 119.18(15) . . ? N1 C1 C2 122.83(16) . . ? N2 C1 C2 117.99(16) . . ? C3 C2 C1 118.76(17) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.29(17) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.39(17) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 123.87(18) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C7 C6 C8 111.03(17) . . ? C7 C6 P1 110.89(13) . . ? C8 C6 P1 109.62(14) . . ? C7 C6 H6 108.4 . . ? C8 C6 H6 108.4 . . ? P1 C6 H6 108.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 110.6(4) . . ? C11 C9 P1 114.3(3) . . ? C10 C9 P1 111.4(4) . . ? C11 C9 H9 106.7 . . ? C10 C9 H9 106.7 . . ? P1 C9 H9 106.7 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10' C9' C11' 110.1(7) . . ? C10' C9' P1 112.5(6) . . ? C11' C9' P1 111.1(4) . . ? C10' C9' H9' 107.7 . . ? C11' C9' H9' 107.7 . . ? P1 C9' H9' 107.7 . . ? C9' C10' H10D 109.5 . . ? C9' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C9' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C9' C11' H11D 109.5 . . ? C9' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C9' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? N3 C12 N4 102.84(14) . . ? N3 C12 Cu1 131.18(12) . . ? N4 C12 Cu1 125.86(13) . . ? C14 C13 N3 106.45(16) . . ? C14 C13 H13 126.8 . . ? N3 C13 H13 126.8 . . ? C13 C14 N4 106.45(15) . . ? C13 C14 H14 126.8 . . ? N4 C14 H14 126.8 . . ? C16 C15 C20 123.69(17) . . ? C16 C15 N3 117.91(16) . . ? C20 C15 N3 118.39(17) . . ? C17 C16 C15 117.00(19) . . ? C17 C16 C21 120.63(19) . . ? C15 C16 C21 122.30(17) . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 121.2(2) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C20 121.1(2) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 116.3(2) . . ? C19 C20 C24 121.89(19) . . ? C15 C20 C24 121.75(18) . . ? C16 C21 C22 109.82(18) . . ? C16 C21 C23 112.7(2) . . ? C22 C21 C23 110.7(2) . . ? C16 C21 H21 107.8 . . ? C22 C21 H21 107.8 . . ? C23 C21 H21 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 C26 111.72(18) . . ? C20 C24 C25 112.9(2) . . ? C26 C24 C25 108.9(2) . . ? C20 C24 H24 107.7 . . ? C26 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C32 123.33(16) . . ? C28 C27 N4 117.79(15) . . ? C32 C27 N4 118.81(15) . . ? C27 C28 C29 117.35(17) . . ? C27 C28 C33 122.06(17) . . ? C29 C28 C33 120.55(17) . . ? C30 C29 C28 120.89(17) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 120.26(18) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C31 C32 121.43(17) . . ? C30 C31 H31 119.3 . . ? C32 C31 H31 119.3 . . ? C31 C32 C27 116.73(16) . . ? C31 C32 C36 121.97(16) . . ? C27 C32 C36 121.29(16) . . ? C34 C33 C28 110.3(2) . . ? C34 C33 C35 111.22(19) . . ? C28 C33 C35 112.35(17) . . ? C34 C33 H33 107.6 . . ? C28 C33 H33 107.6 . . ? C35 C33 H33 107.6 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C36 C38 111.01(15) . . ? C32 C36 C37 113.19(16) . . ? C38 C36 C37 110.06(16) . . ? C32 C36 H36 107.4 . . ? C38 C36 H36 107.4 . . ? C37 C36 H36 107.4 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? F3 Sb1 F5 91.15(6) . . ? F3 Sb1 F6 89.56(8) . . ? F5 Sb1 F6 179.12(7) . . ? F3 Sb1 F4 178.72(7) . . ? F5 Sb1 F4 89.31(7) . . ? F6 Sb1 F4 89.97(8) . . ? F3 Sb1 F2 90.75(8) . . ? F5 Sb1 F2 90.10(6) . . ? F6 Sb1 F2 90.42(7) . . ? F4 Sb1 F2 90.44(7) . . ? F3 Sb1 F1 90.89(7) . . ? F5 Sb1 F1 89.72(6) . . ? F6 Sb1 F1 89.74(6) . . ? F4 Sb1 F1 87.92(6) . . ? F2 Sb1 F1 178.35(7) . . ? 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 C12 Cu1 S1 P1 -164.43(6) . . . . ? N1 Cu1 S1 P1 19.48(5) . . . . ? Cu1 S1 P1 N2 -49.53(7) . . . . ? Cu1 S1 P1 C9' 82.8(2) . . . . ? Cu1 S1 P1 C6 -163.50(7) . . . . ? Cu1 S1 P1 C9 65.97(13) . . . . ? C12 Cu1 N1 C1 -156.46(14) . . . . ? S1 Cu1 N1 C1 18.63(16) . . . . ? C12 Cu1 N1 C5 1.12(18) . . . . ? S1 Cu1 N1 C5 176.22(12) . . . . ? C9' P1 N2 C1 -68.4(3) . . . . ? C6 P1 N2 C1 -178.53(17) . . . . ? C9 P1 N2 C1 -61.5(2) . . . . ? S1 P1 N2 C1 61.07(19) . . . . ? C5 N1 C1 N2 175.18(17) . . . . ? Cu1 N1 C1 N2 -28.0(2) . . . . ? C5 N1 C1 C2 -4.4(3) . . . . ? Cu1 N1 C1 C2 152.50(14) . . . . ? P1 N2 C1 N1 -13.0(3) . . . . ? P1 N2 C1 C2 166.61(15) . . . . ? N1 C1 C2 C3 2.0(3) . . . . ? N2 C1 C2 C3 -177.50(17) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C2 C3 C4 C5 -1.7(3) . . . . ? C1 N1 C5 C4 3.8(3) . . . . ? Cu1 N1 C5 C4 -156.17(16) . . . . ? C3 C4 C5 N1 -0.8(3) . . . . ? N2 P1 C6 C7 -64.11(15) . . . . ? C9' P1 C6 C7 175.9(2) . . . . ? C9 P1 C6 C7 -171.67(17) . . . . ? S1 P1 C6 C7 57.83(14) . . . . ? N2 P1 C6 C8 172.94(14) . . . . ? C9' P1 C6 C8 53.0(3) . . . . ? C9 P1 C6 C8 65.38(19) . . . . ? S1 P1 C6 C8 -65.13(15) . . . . ? N2 P1 C9 C11 165.9(3) . . . . ? C6 P1 C9 C11 -86.8(3) . . . . ? S1 P1 C9 C11 42.9(3) . . . . ? N2 P1 C9 C10 -67.9(4) . . . . ? C9' P1 C9 C10 88.8(11) . . . . ? C6 P1 C9 C10 39.5(4) . . . . ? S1 P1 C9 C10 169.2(3) . . . . ? N2 P1 C9' C10' -53.5(7) . . . . ? C6 P1 C9' C10' 55.5(7) . . . . ? S1 P1 C9' C10' 175.0(6) . . . . ? N2 P1 C9' C11' 70.3(4) . . . . ? C6 P1 C9' C11' 179.4(4) . . . . ? S1 P1 C9' C11' -61.2(4) . . . . ? C13 N3 C12 N4 1.41(19) . . . . ? C15 N3 C12 N4 179.59(16) . . . . ? C13 N3 C12 Cu1 -174.54(14) . . . . ? C15 N3 C12 Cu1 3.6(3) . . . . ? C14 N4 C12 N3 -1.04(19) . . . . ? C27 N4 C12 N3 178.20(15) . . . . ? C14 N4 C12 Cu1 175.20(13) . . . . ? C27 N4 C12 Cu1 -5.6(2) . . . . ? N1 Cu1 C12 N3 -13.9(2) . . . . ? S1 Cu1 C12 N3 171.42(14) . . . . ? N1 Cu1 C12 N4 170.98(12) . . . . ? S1 Cu1 C12 N4 -3.71(17) . . . . ? C12 N3 C13 C14 -1.3(2) . . . . ? C15 N3 C13 C14 -179.55(16) . . . . ? N3 C13 C14 N4 0.6(2) . . . . ? C12 N4 C14 C13 0.3(2) . . . . ? C27 N4 C14 C13 -178.96(16) . . . . ? C12 N3 C15 C16 -94.2(2) . . . . ? C13 N3 C15 C16 83.8(2) . . . . ? C12 N3 C15 C20 86.8(2) . . . . ? C13 N3 C15 C20 -95.2(2) . . . . ? C20 C15 C16 C17 0.9(3) . . . . ? N3 C15 C16 C17 -178.09(16) . . . . ? C20 C15 C16 C21 -176.20(17) . . . . ? N3 C15 C16 C21 4.8(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C21 C16 C17 C18 177.19(19) . . . . ? C16 C17 C18 C19 -1.0(3) . . . . ? C17 C18 C19 C20 1.1(3) . . . . ? C18 C19 C20 C15 -0.2(3) . . . . ? C18 C19 C20 C24 -178.45(19) . . . . ? C16 C15 C20 C19 -0.8(3) . . . . ? N3 C15 C20 C19 178.18(16) . . . . ? C16 C15 C20 C24 177.42(17) . . . . ? N3 C15 C20 C24 -3.6(3) . . . . ? C17 C16 C21 C22 -71.7(3) . . . . ? C15 C16 C21 C22 105.4(2) . . . . ? C17 C16 C21 C23 52.3(3) . . . . ? C15 C16 C21 C23 -130.7(2) . . . . ? C19 C20 C24 C26 -100.2(2) . . . . ? C15 C20 C24 C26 81.7(2) . . . . ? C19 C20 C24 C25 23.0(3) . . . . ? C15 C20 C24 C25 -155.14(19) . . . . ? C12 N4 C27 C28 107.3(2) . . . . ? C14 N4 C27 C28 -73.5(2) . . . . ? C12 N4 C27 C32 -75.7(2) . . . . ? C14 N4 C27 C32 103.5(2) . . . . ? C32 C27 C28 C29 -0.1(3) . . . . ? N4 C27 C28 C29 176.74(16) . . . . ? C32 C27 C28 C33 177.71(19) . . . . ? N4 C27 C28 C33 -5.4(3) . . . . ? C27 C28 C29 C30 -0.9(3) . . . . ? C33 C28 C29 C30 -178.81(19) . . . . ? C28 C29 C30 C31 1.2(3) . . . . ? C29 C30 C31 C32 -0.3(3) . . . . ? C30 C31 C32 C27 -0.7(3) . . . . ? C30 C31 C32 C36 -179.61(17) . . . . ? C28 C27 C32 C31 0.9(3) . . . . ? N4 C27 C32 C31 -175.91(15) . . . . ? C28 C27 C32 C36 179.86(17) . . . . ? N4 C27 C32 C36 3.0(2) . . . . ? C27 C28 C33 C34 -101.5(3) . . . . ? C29 C28 C33 C34 76.3(3) . . . . ? C27 C28 C33 C35 133.9(2) . . . . ? C29 C28 C33 C35 -48.4(3) . . . . ? C31 C32 C36 C38 100.8(2) . . . . ? C27 C32 C36 C38 -78.1(2) . . . . ? C31 C32 C36 C37 -23.6(2) . . . . ? C27 C32 C36 C37 157.57(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N F1 0.88 2.15 3.023(2) 169.6 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.806 _refine_diff_density_min -0.910 _refine_diff_density_rms 0.073 #===END # 1476 [Cu(SPN-iPr)2]PF6 in Pn data_8b-1476 _database_code_depnum_ccdc_archive 'CCDC 810373' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449_ #5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1476 (Cu(SPN-iPr)2)PF6 at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C22 H38 Cu N4 P2 S2, F6 P' _chemical_formula_sum 'C22 H38 Cu F6 N4 P3 S2' _chemical_formula_weight 693.13 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 Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.8770(6) _cell_length_b 13.3222(10) _cell_length_c 14.8577(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.9530(10) _cell_angle_gamma 90.00 _cell_volume 1525.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8949 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 30.04 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from dichloromethane by evaporation. Bruker Smart APEX CCD 3-axis diffractometer. The structure shows an non-crystallographic pseudosymmetry with all [Cu(SPN-iPr)2] complexes aligned along [10-1] in the form of columns with practically perfect local non-crystallographic C2-symmetry, which involves also the nearby PF6 octahedra. ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 13666 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6486 _reflns_number_gt 6136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0799P)^2^+0.0469P] 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_abs_structure_details 'Flack (1983), 2063 Friedel pairs' _refine_ls_abs_structure_Flack 0.001(8) _refine_ls_number_reflns 6486 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.062 _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 0.50018(7) 0.49740(2) 0.50016(4) 0.01871(9) Uani 1 1 d . . . S1 S 0.70629(8) 0.61481(4) 0.49769(5) 0.01966(13) Uani 1 1 d D . . P1 P 0.53886(8) 0.72794(4) 0.48529(4) 0.01534(13) Uani 1 1 d D . . N1 N 0.2842(2) 0.57185(14) 0.53760(13) 0.0184(4) Uani 1 1 d D . . N2 N 0.4161(2) 0.73027(13) 0.56493(13) 0.0190(4) Uani 1 1 d D . . H2N H 0.4266 0.7846 0.5994 0.023 Uiso 1 1 calc R . . C1 C 0.2997(3) 0.65881(15) 0.58456(14) 0.0174(5) Uani 1 1 d D . . C2 C 0.2061(3) 0.67987(18) 0.65264(16) 0.0230(5) Uani 1 1 d D . . H2 H 0.2183 0.7427 0.6835 0.028 Uiso 1 1 calc R . . C3 C 0.0954(3) 0.60711(18) 0.67399(17) 0.0251(6) Uani 1 1 d D . . H3 H 0.0337 0.6183 0.7217 0.030 Uiso 1 1 calc R . . C4 C 0.0753(3) 0.51697(19) 0.62462(18) 0.0241(6) Uani 1 1 d D . . H4 H -0.0021 0.4666 0.6369 0.029 Uiso 1 1 calc R . . C5 C 0.1705(3) 0.50327(15) 0.55799(17) 0.0205(6) Uani 1 1 d D . . H5 H 0.1558 0.4423 0.5242 0.025 Uiso 1 1 calc R . . C6 C 0.6536(2) 0.84774(15) 0.50711(14) 0.0211(5) Uani 1 1 d D . . H6 H 0.5657 0.9023 0.5052 0.025 Uiso 1 1 calc R . . C7 C 0.7566(4) 0.8687(2) 0.43244(19) 0.0306(6) Uani 1 1 d D . . H7A H 0.8253 0.9300 0.4478 0.046 Uiso 1 1 calc R . . H7B H 0.6763 0.8774 0.3731 0.046 Uiso 1 1 calc R . . H7C H 0.8344 0.8121 0.4286 0.046 Uiso 1 1 calc R . . C8 C 0.7742(3) 0.8478(2) 0.60319(17) 0.0284(6) Uani 1 1 d D . . H8A H 0.8671 0.7985 0.6046 0.043 Uiso 1 1 calc R . . H8B H 0.7072 0.8302 0.6496 0.043 Uiso 1 1 calc R . . H8C H 0.8250 0.9147 0.6164 0.043 Uiso 1 1 calc R . . C9 C 0.3833(2) 0.72912(15) 0.37483(14) 0.0205(5) Uani 1 1 d D . . H9 H 0.2931 0.6779 0.3802 0.025 Uiso 1 1 calc R . . C10 C 0.4604(4) 0.6966(2) 0.29306(15) 0.0310(7) Uani 1 1 d D . . H10A H 0.3665 0.6845 0.2396 0.047 Uiso 1 1 calc R . . H10B H 0.5276 0.6349 0.3087 0.047 Uiso 1 1 calc R . . H10C H 0.5365 0.7497 0.2785 0.047 Uiso 1 1 calc R . . C11 C 0.2879(4) 0.83021(18) 0.35948(19) 0.0316(7) Uani 1 1 d D . . H11A H 0.3713 0.8837 0.3551 0.047 Uiso 1 1 calc R . . H11B H 0.2319 0.8440 0.4112 0.047 Uiso 1 1 calc R . . H11C H 0.1998 0.8275 0.3023 0.047 Uiso 1 1 calc R . . S2 S 0.40407(9) 0.37618(4) 0.39445(5) 0.01964(14) Uani 1 1 d D . . P2 P 0.51056(7) 0.26624(4) 0.47759(4) 0.01508(14) Uani 1 1 d D . . N3 N 0.5558(3) 0.42335(14) 0.63255(11) 0.0187(4) Uani 1 1 d D . . N4 N 0.4518(2) 0.26418(13) 0.57990(12) 0.0177(4) Uani 1 1 d D . . H4N H 0.3962 0.2100 0.5915 0.021 Uiso 1 1 calc R . . C12 C 0.4793(3) 0.33689(15) 0.64901(13) 0.0169(5) Uani 1 1 d D . . C13 C 0.4276(3) 0.31681(17) 0.73155(14) 0.0198(5) Uani 1 1 d D . . H13 H 0.3729 0.2551 0.7405 0.024 Uiso 1 1 calc R . . C14 C 0.4577(3) 0.38897(18) 0.80012(15) 0.0230(5) Uani 1 1 d D . . H14 H 0.4213 0.3782 0.8565 0.028 Uiso 1 1 calc R . . C15 C 0.5422(4) 0.47793(19) 0.78541(15) 0.0234(5) Uani 1 1 d D . . H15 H 0.5670 0.5279 0.8319 0.028 Uiso 1 1 calc R . . C16 C 0.5886(3) 0.49129(15) 0.70219(16) 0.0202(5) Uani 1 1 d D . . H16 H 0.6471 0.5515 0.6927 0.024 Uiso 1 1 calc R . . C17 C 0.4332(3) 0.14391(15) 0.43088(14) 0.0197(5) Uani 1 1 d D . . H17 H 0.4784 0.0917 0.4782 0.024 Uiso 1 1 calc R . . C18 C 0.5028(4) 0.12053(18) 0.34445(17) 0.0256(6) Uani 1 1 d D . . H18A H 0.6279 0.1082 0.3615 0.038 Uiso 1 1 calc R . . H18B H 0.4805 0.1777 0.3021 0.038 Uiso 1 1 calc R . . H18C H 0.4444 0.0608 0.3143 0.038 Uiso 1 1 calc R . . C19 C 0.2334(3) 0.13934(19) 0.4106(2) 0.0263(6) Uani 1 1 d D . . H19A H 0.1864 0.1864 0.3610 0.040 Uiso 1 1 calc R . . H19B H 0.1915 0.1576 0.4660 0.040 Uiso 1 1 calc R . . H19C H 0.1952 0.0711 0.3917 0.040 Uiso 1 1 calc R . . C20 C 0.7485(2) 0.27149(15) 0.50589(15) 0.0214(5) Uani 1 1 d D . . H20 H 0.7795 0.3255 0.5532 0.026 Uiso 1 1 calc R . . C21 C 0.8300(3) 0.3022(2) 0.42512(18) 0.0299(6) Uani 1 1 d D . . H21A H 0.9535 0.3166 0.4476 0.045 Uiso 1 1 calc R . . H21B H 0.7715 0.3623 0.3957 0.045 Uiso 1 1 calc R . . H21C H 0.8172 0.2473 0.3803 0.045 Uiso 1 1 calc R . . C22 C 0.8244(3) 0.17380(19) 0.55247(19) 0.0289(6) Uani 1 1 d D . . H22A H 0.8092 0.1196 0.5070 0.043 Uiso 1 1 calc R . . H22B H 0.7643 0.1565 0.6018 0.043 Uiso 1 1 calc R . . H22C H 0.9484 0.1831 0.5783 0.043 Uiso 1 1 calc R . . P3 P 0.34312(12) 0.99668(5) 0.67554(6) 0.01859(15) Uani 1 1 d . . . F1 F 0.4354(3) 0.89049(12) 0.70664(13) 0.0312(4) Uani 1 1 d . . . F2 F 0.2520(3) 1.10337(13) 0.64292(14) 0.0302(4) Uani 1 1 d . . . F3 F 0.2939(3) 0.95699(14) 0.57161(12) 0.0384(5) Uani 1 1 d . . . F4 F 0.3975(3) 1.03644(18) 0.77819(14) 0.0435(5) Uani 1 1 d . . . F5 F 0.5224(3) 1.03931(15) 0.65520(17) 0.0392(5) Uani 1 1 d . . . F6 F 0.1656(3) 0.95485(18) 0.69351(17) 0.0444(5) 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 Cu1 0.02017(16) 0.01507(15) 0.02030(16) -0.00004(10) 0.00288(11) 0.00094(11) S1 0.0162(3) 0.0188(3) 0.0234(3) 0.0028(2) 0.0028(2) 0.0021(2) P1 0.0151(3) 0.0139(3) 0.0158(3) 0.0003(2) 0.0004(2) -0.0005(2) N1 0.0159(9) 0.0156(9) 0.0220(10) 0.0020(8) 0.0003(7) -0.0008(8) N2 0.0208(11) 0.0169(10) 0.0206(10) -0.0035(8) 0.0074(8) -0.0012(8) C1 0.0166(11) 0.0156(10) 0.0183(10) 0.0013(8) -0.0002(8) 0.0030(9) C2 0.0203(12) 0.0250(13) 0.0230(12) -0.0030(10) 0.0031(9) 0.0007(10) C3 0.0208(13) 0.0322(15) 0.0233(12) 0.0004(11) 0.0070(10) 0.0017(11) C4 0.0163(12) 0.0257(13) 0.0289(14) 0.0045(11) 0.0017(10) -0.0007(10) C5 0.0162(12) 0.0182(13) 0.0252(13) 0.0030(9) 0.0001(10) -0.0018(9) C6 0.0197(12) 0.0186(12) 0.0246(12) -0.0010(9) 0.0034(9) -0.0043(10) C7 0.0296(15) 0.0285(14) 0.0348(15) -0.0002(12) 0.0089(12) -0.0082(12) C8 0.0224(13) 0.0293(14) 0.0294(14) -0.0063(11) -0.0040(11) -0.0066(11) C9 0.0177(12) 0.0204(12) 0.0201(11) 0.0011(9) -0.0035(9) -0.0019(9) C10 0.0309(15) 0.0388(17) 0.0203(12) -0.0022(11) -0.0018(11) -0.0007(13) C11 0.0268(14) 0.0250(13) 0.0361(15) 0.0060(12) -0.0091(12) 0.0039(12) S2 0.0223(3) 0.0184(3) 0.0161(3) 0.0009(2) -0.0009(2) 0.0043(2) P2 0.0155(3) 0.0140(3) 0.0143(3) -0.0004(2) -0.0001(2) 0.0016(2) N3 0.0193(10) 0.0165(10) 0.0176(9) -0.0007(8) -0.0023(7) 0.0011(8) N4 0.0216(10) 0.0158(9) 0.0155(9) -0.0008(7) 0.0035(7) -0.0014(8) C12 0.0136(10) 0.0162(11) 0.0182(11) -0.0001(8) -0.0026(8) 0.0038(8) C13 0.0201(12) 0.0209(12) 0.0182(11) 0.0000(9) 0.0035(9) -0.0003(10) C14 0.0229(13) 0.0278(14) 0.0176(11) -0.0025(9) 0.0022(9) 0.0000(10) C15 0.0210(12) 0.0258(12) 0.0211(12) -0.0052(10) -0.0006(10) 0.0012(11) C16 0.0198(13) 0.0184(12) 0.0196(12) -0.0019(8) -0.0023(10) -0.0002(9) C17 0.0228(12) 0.0178(11) 0.0172(11) -0.0035(9) 0.0008(9) 0.0009(10) C18 0.0330(15) 0.0221(13) 0.0213(12) -0.0063(10) 0.0051(11) 0.0004(11) C19 0.0209(13) 0.0261(13) 0.0292(13) -0.0036(11) -0.0015(10) -0.0017(11) C20 0.0162(11) 0.0235(12) 0.0226(12) -0.0011(9) -0.0008(9) 0.0021(9) C21 0.0205(13) 0.0364(16) 0.0327(15) 0.0010(12) 0.0054(11) -0.0033(12) C22 0.0233(14) 0.0294(14) 0.0302(14) 0.0016(11) -0.0029(11) 0.0092(12) P3 0.0203(3) 0.0170(3) 0.0187(3) -0.0025(2) 0.0045(2) -0.0029(2) F1 0.0410(11) 0.0232(8) 0.0267(9) 0.0013(7) 0.0006(7) 0.0012(8) F2 0.0250(9) 0.0227(8) 0.0421(10) 0.0011(7) 0.0051(7) 0.0032(7) F3 0.0586(13) 0.0323(10) 0.0201(8) -0.0054(7) -0.0016(8) 0.0033(10) F4 0.0489(13) 0.0508(13) 0.0263(9) -0.0174(9) -0.0024(8) 0.0086(11) F5 0.0236(9) 0.0339(11) 0.0634(14) 0.0057(10) 0.0167(9) -0.0011(8) F6 0.0279(10) 0.0491(14) 0.0577(14) 0.0154(11) 0.0126(9) -0.0104(10) _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 N1 2.1398(19) . ? Cu1 N3 2.1628(18) . ? Cu1 S1 2.2602(8) . ? Cu1 S2 2.2706(7) . ? S1 P1 1.9860(7) . ? P1 N2 1.676(2) . ? P1 C6 1.830(2) . ? P1 C9 1.8337(18) . ? N1 C1 1.345(3) . ? N1 C5 1.357(3) . ? N2 C1 1.394(3) . ? N2 H2N 0.8800 . ? C1 C2 1.398(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C4 C5 1.372(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.530(3) . ? C6 C8 1.543(3) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.529(3) . ? C9 C11 1.536(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? S2 P2 1.9863(7) . ? P2 N4 1.678(2) . ? P2 C17 1.826(2) . ? P2 C20 1.8354(18) . ? N3 C12 1.345(3) . ? N3 C16 1.359(3) . ? N4 C12 1.396(2) . ? N4 H4N 0.8800 . ? C12 C13 1.396(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.399(3) . ? C14 H14 0.9500 . ? C15 C16 1.371(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.529(3) . ? C17 C19 1.541(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.529(3) . ? C20 C22 1.536(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? P3 F6 1.578(2) . ? P3 F4 1.587(2) . ? P3 F3 1.6019(19) . ? P3 F5 1.608(2) . ? P3 F1 1.6137(18) . ? P3 F2 1.6205(18) . ? 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 Cu1 N3 89.84(9) . . ? N1 Cu1 S1 107.21(5) . . ? N3 Cu1 S1 108.63(5) . . ? N1 Cu1 S2 109.90(5) . . ? N3 Cu1 S2 106.29(5) . . ? S1 Cu1 S2 128.22(4) . . ? P1 S1 Cu1 93.51(3) . . ? N2 P1 C6 101.23(9) . . ? N2 P1 C9 104.80(9) . . ? C6 P1 C9 111.41(9) . . ? N2 P1 S1 114.69(7) . . ? C6 P1 S1 110.58(7) . . ? C9 P1 S1 113.41(7) . . ? C1 N1 C5 117.21(18) . . ? C1 N1 Cu1 122.85(14) . . ? C5 N1 Cu1 110.08(15) . . ? C1 N2 P1 129.47(14) . . ? C1 N2 H2N 115.3 . . ? P1 N2 H2N 115.3 . . ? N1 C1 N2 118.22(18) . . ? N1 C1 C2 122.92(18) . . ? N2 C1 C2 118.86(18) . . ? C3 C2 C1 118.50(19) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.24(19) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.79(19) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C7 C6 C8 110.68(18) . . ? C7 C6 P1 110.33(15) . . ? C8 C6 P1 110.57(14) . . ? C7 C6 H6 108.4 . . ? C8 C6 H6 108.4 . . ? P1 C6 H6 108.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 113.12(19) . . ? C10 C9 P1 114.02(14) . . ? C11 C9 P1 110.85(14) . . ? C10 C9 H9 106.0 . . ? C11 C9 H9 106.0 . . ? P1 C9 H9 106.0 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P2 S2 Cu1 93.26(3) . . ? N4 P2 C17 101.34(9) . . ? N4 P2 C20 104.67(9) . . ? C17 P2 C20 111.46(9) . . ? N4 P2 S2 114.53(7) . . ? C17 P2 S2 110.92(7) . . ? C20 P2 S2 113.21(7) . . ? C12 N3 C16 116.98(18) . . ? C12 N3 Cu1 122.80(12) . . ? C16 N3 Cu1 111.07(14) . . ? C12 N4 P2 128.69(14) . . ? C12 N4 H4N 115.7 . . ? P2 N4 H4N 115.7 . . ? N3 C12 N4 117.89(18) . . ? N3 C12 C13 123.16(18) . . ? N4 C12 C13 118.96(18) . . ? C14 C13 C12 118.45(19) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 118.37(19) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? N3 C16 C15 123.78(19) . . ? N3 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? C18 C17 C19 110.89(17) . . ? C18 C17 P2 110.57(15) . . ? C19 C17 P2 110.90(14) . . ? C18 C17 H17 108.1 . . ? C19 C17 H17 108.1 . . ? P2 C17 H17 108.1 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 113.11(19) . . ? C21 C20 P2 113.90(14) . . ? C22 C20 P2 110.79(14) . . ? C21 C20 H20 106.1 . . ? C22 C20 H20 106.1 . . ? P2 C20 H20 106.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? F6 P3 F4 91.57(15) . . ? F6 P3 F3 90.03(13) . . ? F4 P3 F3 178.35(15) . . ? F6 P3 F5 178.93(13) . . ? F4 P3 F5 89.43(13) . . ? F3 P3 F5 88.97(14) . . ? F6 P3 F1 90.25(12) . . ? F4 P3 F1 90.09(11) . . ? F3 P3 F1 89.50(10) . . ? F5 P3 F1 90.13(12) . . ? F6 P3 F2 90.41(12) . . ? F4 P3 F2 90.53(12) . . ? F3 P3 F2 89.86(11) . . ? F5 P3 F2 89.20(11) . . ? F1 P3 F2 179.08(13) . . ? 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 N1 Cu1 S1 P1 -20.31(7) . . . . ? N3 Cu1 S1 P1 -116.13(7) . . . . ? S2 Cu1 S1 P1 113.91(3) . . . . ? Cu1 S1 P1 N2 53.02(7) . . . . ? Cu1 S1 P1 C6 166.69(8) . . . . ? Cu1 S1 P1 C9 -67.34(9) . . . . ? N3 Cu1 N1 C1 86.12(18) . . . . ? S1 Cu1 N1 C1 -23.37(19) . . . . ? S2 Cu1 N1 C1 -166.59(16) . . . . ? N3 Cu1 N1 C5 -58.53(15) . . . . ? S1 Cu1 N1 C5 -168.02(14) . . . . ? S2 Cu1 N1 C5 48.76(16) . . . . ? C6 P1 N2 C1 -179.09(19) . . . . ? C9 P1 N2 C1 65.0(2) . . . . ? S1 P1 N2 C1 -60.0(2) . . . . ? C5 N1 C1 N2 179.9(2) . . . . ? Cu1 N1 C1 N2 37.5(3) . . . . ? C5 N1 C1 C2 0.7(3) . . . . ? Cu1 N1 C1 C2 -141.7(2) . . . . ? P1 N2 C1 N1 3.4(3) . . . . ? P1 N2 C1 C2 -177.41(18) . . . . ? N1 C1 C2 C3 1.4(4) . . . . ? N2 C1 C2 C3 -177.7(2) . . . . ? C1 C2 C3 C4 -2.6(4) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C1 N1 C5 C4 -1.7(4) . . . . ? Cu1 N1 C5 C4 145.2(2) . . . . ? C3 C4 C5 N1 0.6(4) . . . . ? N2 P1 C6 C7 -172.13(16) . . . . ? C9 P1 C6 C7 -61.19(19) . . . . ? S1 P1 C6 C7 65.90(17) . . . . ? N2 P1 C6 C8 65.10(18) . . . . ? C9 P1 C6 C8 176.04(17) . . . . ? S1 P1 C6 C8 -56.87(18) . . . . ? N2 P1 C9 C10 -162.95(17) . . . . ? C6 P1 C9 C10 88.40(19) . . . . ? S1 P1 C9 C10 -37.13(19) . . . . ? N2 P1 C9 C11 68.0(2) . . . . ? C6 P1 C9 C11 -40.6(2) . . . . ? S1 P1 C9 C11 -166.17(17) . . . . ? N1 Cu1 S2 P2 -116.36(6) . . . . ? N3 Cu1 S2 P2 -20.46(7) . . . . ? S1 Cu1 S2 P2 110.36(4) . . . . ? Cu1 S2 P2 N4 54.80(7) . . . . ? Cu1 S2 P2 C17 168.74(8) . . . . ? Cu1 S2 P2 C20 -65.09(9) . . . . ? N1 Cu1 N3 C12 85.98(19) . . . . ? S1 Cu1 N3 C12 -165.88(17) . . . . ? S2 Cu1 N3 C12 -24.7(2) . . . . ? N1 Cu1 N3 C16 -59.78(17) . . . . ? S1 Cu1 N3 C16 48.36(18) . . . . ? S2 Cu1 N3 C16 -170.50(16) . . . . ? C17 P2 N4 C12 178.46(19) . . . . ? C20 P2 N4 C12 62.5(2) . . . . ? S2 P2 N4 C12 -62.1(2) . . . . ? C16 N3 C12 N4 -177.1(2) . . . . ? Cu1 N3 C12 N4 39.0(3) . . . . ? C16 N3 C12 C13 2.6(3) . . . . ? Cu1 N3 C12 C13 -141.3(2) . . . . ? P2 N4 C12 N3 3.4(3) . . . . ? P2 N4 C12 C13 -176.34(18) . . . . ? N3 C12 C13 C14 -0.6(4) . . . . ? N4 C12 C13 C14 179.1(2) . . . . ? C12 C13 C14 C15 -1.6(4) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C12 N3 C16 C15 -2.7(4) . . . . ? Cu1 N3 C16 C15 145.3(2) . . . . ? C14 C15 C16 N3 0.6(4) . . . . ? N4 P2 C17 C18 -169.38(16) . . . . ? C20 P2 C17 C18 -58.51(18) . . . . ? S2 P2 C17 C18 68.62(16) . . . . ? N4 P2 C17 C19 67.18(18) . . . . ? C20 P2 C17 C19 178.05(17) . . . . ? S2 P2 C17 C19 -54.82(18) . . . . ? N4 P2 C20 C21 -164.39(17) . . . . ? C17 P2 C20 C21 86.87(19) . . . . ? S2 P2 C20 C21 -39.01(19) . . . . ? N4 P2 C20 C22 66.75(19) . . . . ? C17 P2 C20 C22 -42.0(2) . . . . ? S2 P2 C20 C22 -167.86(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N F1 0.88 2.12 2.980(3) 165.7 . N2 H2N F3 0.88 2.52 3.178(3) 131.9 . C2 H2 F1 0.95 2.58 3.343(3) 137.1 . N4 H4N F2 0.88 2.06 2.925(3) 166.6 1_545 N4 H4N F5 0.88 2.58 3.206(3) 128.7 1_545 C13 H13 F2 0.95 2.55 3.313(3) 137.1 1_545 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.823 _refine_diff_density_min -0.979 _refine_diff_density_rms 0.115 #===END # 1499 [Cu2(SPN-Ph)2(CH3CN)2](SbF6)2.2(Et2O) data_11a-1499 _database_code_depnum_ccdc_archive 'CCDC 810374' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_ #3b449_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1499 (Cu2(SPN-Ph)2(CH3CN)2)(SbF6)2.2(Et2O) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C38 H36 Cu2 N6 P2 S2, 2(C4 H10 O), 2(F6 Sb)' _chemical_formula_sum 'C46 H56 Cu2 F12 N6 O2 P2 S2 Sb2' _chemical_formula_weight 1449.61 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2387(5) _cell_length_b 14.4373(7) _cell_length_c 21.7631(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.035(2) _cell_angle_gamma 90.00 _cell_volume 2839.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9883 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 30.05 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.48 _exptl_absorpt_correction_T_max 0.56 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Large block-like crystals from acetone / diethyl ether by vapour diffusion. Bruker Kappa APEX-2 CCD diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 60222 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8250 _reflns_number_gt 7816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0242P)^2^+3.0506P] 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 8250 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.002 _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 0.44793(2) 0.566938(15) 0.458965(10) 0.02302(5) Uani 1 1 d . . . P1 P 0.19576(4) 0.43612(3) 0.414873(18) 0.01573(7) Uani 1 1 d . . . S1 S 0.29249(4) 0.47166(3) 0.502358(17) 0.02086(7) Uani 1 1 d . . . N1 N 0.46624(14) 0.51749(10) 0.37167(6) 0.0203(2) Uani 1 1 d . . . N2 N 0.30472(14) 0.39129(10) 0.37065(6) 0.0196(2) Uani 1 1 d . . . H2N H 0.2907 0.3324 0.3608 0.024 Uiso 1 1 calc R . . N3 N 0.38773(17) 0.69762(11) 0.45502(7) 0.0282(3) Uani 1 1 d . . . C1 C 0.41568(17) 0.43595(11) 0.34734(8) 0.0207(3) Uani 1 1 d . . . C2 C 0.4696(2) 0.39351(15) 0.29897(10) 0.0349(4) Uani 1 1 d . . . H2 H 0.4343 0.3343 0.2836 0.042 Uiso 1 1 calc R . . C3 C 0.5748(3) 0.43922(16) 0.27398(12) 0.0409(5) Uani 1 1 d . . . H3 H 0.6115 0.4123 0.2404 0.049 Uiso 1 1 calc R . . C4 C 0.6268(2) 0.52430(15) 0.29793(9) 0.0322(4) Uani 1 1 d . . . H4 H 0.6991 0.5569 0.2812 0.039 Uiso 1 1 calc R . . C5 C 0.57120(18) 0.56030(13) 0.34641(8) 0.0253(3) Uani 1 1 d . . . H5 H 0.6080 0.6184 0.3633 0.030 Uiso 1 1 calc R . . C6 C 0.10051(15) 0.53335(10) 0.37283(7) 0.0169(3) Uani 1 1 d . . . C7 C 0.03597(18) 0.59919(12) 0.40579(8) 0.0225(3) Uani 1 1 d . . . H7 H 0.0449 0.5933 0.4499 0.027 Uiso 1 1 calc R . . C8 C -0.04107(19) 0.67310(12) 0.37398(9) 0.0269(3) Uani 1 1 d . . . H8 H -0.0864 0.7175 0.3961 0.032 Uiso 1 1 calc R . . C9 C -0.05201(19) 0.68223(12) 0.30933(9) 0.0260(3) Uani 1 1 d . . . H9 H -0.1033 0.7336 0.2877 0.031 Uiso 1 1 calc R . . C10 C 0.01129(18) 0.61713(12) 0.27654(8) 0.0242(3) Uani 1 1 d . . . H10 H 0.0033 0.6237 0.2325 0.029 Uiso 1 1 calc R . . C11 C 0.08687(17) 0.54176(11) 0.30804(7) 0.0203(3) Uani 1 1 d . . . H11 H 0.1289 0.4963 0.2855 0.024 Uiso 1 1 calc R . . C12 C 0.06465(16) 0.34462(11) 0.41570(7) 0.0190(3) Uani 1 1 d . . . C13 C -0.0622(2) 0.33756(15) 0.36854(10) 0.0364(5) Uani 1 1 d . . . H13 H -0.0821 0.3822 0.3358 0.044 Uiso 1 1 calc R . . C14 C -0.1595(3) 0.26461(17) 0.36982(12) 0.0476(6) Uani 1 1 d . . . H14 H -0.2459 0.2591 0.3376 0.057 Uiso 1 1 calc R . . C15 C -0.1314(2) 0.19989(14) 0.41764(10) 0.0355(4) Uani 1 1 d . . . H15 H -0.1999 0.1511 0.4187 0.043 Uiso 1 1 calc R . . C16 C -0.0048(2) 0.20587(13) 0.46371(9) 0.0294(4) Uani 1 1 d . . . H16 H 0.0151 0.1604 0.4960 0.035 Uiso 1 1 calc R . . C17 C 0.09412(19) 0.27841(12) 0.46312(8) 0.0235(3) Uani 1 1 d . . . H17 H 0.1815 0.2827 0.4950 0.028 Uiso 1 1 calc R . . C18 C 0.33495(19) 0.76900(13) 0.44558(8) 0.0271(3) Uani 1 1 d . . . C19 C 0.2682(2) 0.86017(14) 0.43304(10) 0.0345(4) Uani 1 1 d . . . H19A H 0.2848 0.8962 0.4721 0.052 Uiso 1 1 calc R . . H19B H 0.1616 0.8534 0.4166 0.052 Uiso 1 1 calc R . . H19C H 0.3131 0.8923 0.4020 0.052 Uiso 1 1 calc R . . Sb1 Sb 0.805700(12) 0.420927(8) 0.128909(5) 0.02230(3) Uani 1 1 d . . . F1 F 0.82080(13) 0.35576(9) 0.20468(5) 0.0348(2) Uani 1 1 d . . . F2 F 0.79025(18) 0.48571(10) 0.05309(6) 0.0462(3) Uani 1 1 d . . . F3 F 0.60229(13) 0.39639(9) 0.10932(6) 0.0373(3) Uani 1 1 d . . . F4 F 1.00879(14) 0.44641(10) 0.15006(7) 0.0427(3) Uani 1 1 d . . . F5 F 0.76784(14) 0.53032(8) 0.16911(6) 0.0358(3) Uani 1 1 d . . . F6 F 0.84169(14) 0.31076(9) 0.08908(6) 0.0390(3) Uani 1 1 d . . . O1 O 0.26588(15) 0.20402(9) 0.32634(6) 0.0306(3) Uani 1 1 d . . . C20 C 0.1486(2) 0.18418(16) 0.27344(11) 0.0419(5) Uani 1 1 d . . . H20A H 0.0525 0.1839 0.2867 0.050 Uiso 1 1 calc R . . H20B H 0.1639 0.1223 0.2563 0.050 Uiso 1 1 calc R . . C21 C 0.1473(3) 0.25682(18) 0.22375(12) 0.0515(6) Uani 1 1 d . . . H21A H 0.1336 0.3180 0.2412 0.077 Uiso 1 1 calc R . . H21B H 0.0658 0.2444 0.1880 0.077 Uiso 1 1 calc R . . H21C H 0.2414 0.2554 0.2098 0.077 Uiso 1 1 calc R . . C22 C 0.2839(2) 0.13123(14) 0.37078(10) 0.0358(4) Uani 1 1 d . . . H22A H 0.3007 0.0722 0.3502 0.043 Uiso 1 1 calc R . . H22B H 0.1931 0.1248 0.3878 0.043 Uiso 1 1 calc R . . C23 C 0.4133(3) 0.15175(17) 0.42311(11) 0.0436(5) Uani 1 1 d . . . H23A H 0.5030 0.1577 0.4061 0.065 Uiso 1 1 calc R . . H23B H 0.4260 0.1012 0.4538 0.065 Uiso 1 1 calc R . . H23C H 0.3956 0.2098 0.4437 0.065 Uiso 1 1 calc 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 0.02108(9) 0.02543(10) 0.02110(9) -0.00256(7) 0.00107(7) -0.00453(7) P1 0.01157(15) 0.01914(17) 0.01510(16) -0.00042(13) -0.00043(12) -0.00181(12) S1 0.01496(15) 0.03010(19) 0.01565(15) -0.00152(14) -0.00113(12) -0.00407(13) N1 0.0164(6) 0.0250(6) 0.0177(6) 0.0001(5) -0.0009(5) -0.0024(5) N2 0.0170(6) 0.0195(6) 0.0222(6) -0.0027(5) 0.0041(5) -0.0014(5) N3 0.0257(7) 0.0298(7) 0.0288(7) -0.0034(6) 0.0045(6) -0.0064(6) C1 0.0146(6) 0.0247(7) 0.0223(7) -0.0010(6) 0.0027(5) 0.0003(5) C2 0.0365(10) 0.0317(9) 0.0420(11) -0.0113(8) 0.0211(8) -0.0055(8) C3 0.0395(11) 0.0429(11) 0.0486(12) -0.0092(9) 0.0282(10) -0.0037(9) C4 0.0230(8) 0.0413(10) 0.0342(9) 0.0019(8) 0.0104(7) -0.0053(7) C5 0.0199(7) 0.0316(8) 0.0221(7) 0.0023(6) -0.0006(6) -0.0070(6) C6 0.0129(6) 0.0182(6) 0.0184(6) -0.0006(5) 0.0001(5) -0.0030(5) C7 0.0208(7) 0.0244(7) 0.0218(7) -0.0014(6) 0.0031(6) 0.0015(6) C8 0.0248(8) 0.0221(7) 0.0328(9) -0.0018(6) 0.0040(6) 0.0035(6) C9 0.0217(7) 0.0214(7) 0.0321(8) 0.0059(6) -0.0004(6) 0.0001(6) C10 0.0215(7) 0.0259(8) 0.0226(7) 0.0056(6) -0.0010(6) -0.0033(6) C11 0.0186(7) 0.0216(7) 0.0195(7) -0.0002(5) 0.0013(5) -0.0022(5) C12 0.0162(6) 0.0205(7) 0.0192(6) 0.0004(5) 0.0012(5) -0.0028(5) C13 0.0291(9) 0.0351(10) 0.0365(10) 0.0133(8) -0.0126(8) -0.0145(8) C14 0.0377(11) 0.0468(12) 0.0476(12) 0.0126(10) -0.0159(9) -0.0257(10) C15 0.0360(10) 0.0312(9) 0.0377(10) 0.0021(8) 0.0039(8) -0.0168(8) C16 0.0364(9) 0.0254(8) 0.0271(8) 0.0045(6) 0.0080(7) -0.0058(7) C17 0.0231(7) 0.0253(8) 0.0210(7) 0.0027(6) 0.0022(6) -0.0026(6) C18 0.0242(8) 0.0298(8) 0.0274(8) -0.0028(7) 0.0056(6) -0.0071(6) C19 0.0353(10) 0.0297(9) 0.0402(10) 0.0023(8) 0.0116(8) 0.0011(7) Sb1 0.02360(6) 0.02154(6) 0.02246(6) -0.00273(4) 0.00643(4) -0.00377(4) F1 0.0337(6) 0.0408(6) 0.0315(6) 0.0113(5) 0.0102(5) 0.0060(5) F2 0.0704(9) 0.0413(7) 0.0285(6) 0.0074(5) 0.0140(6) -0.0004(6) F3 0.0238(5) 0.0374(6) 0.0469(7) -0.0072(5) -0.0010(5) -0.0021(5) F4 0.0262(6) 0.0489(7) 0.0552(8) -0.0048(6) 0.0135(5) -0.0105(5) F5 0.0453(7) 0.0263(5) 0.0339(6) -0.0100(4) 0.0035(5) 0.0018(5) F6 0.0434(7) 0.0311(6) 0.0440(7) -0.0133(5) 0.0124(5) 0.0032(5) O1 0.0299(6) 0.0250(6) 0.0324(7) -0.0048(5) -0.0037(5) 0.0006(5) C20 0.0323(10) 0.0389(11) 0.0471(12) -0.0137(9) -0.0089(9) 0.0047(8) C21 0.0497(13) 0.0455(13) 0.0477(13) -0.0077(10) -0.0164(11) 0.0122(11) C22 0.0391(10) 0.0306(9) 0.0376(10) -0.0059(8) 0.0075(8) -0.0040(8) C23 0.0506(13) 0.0394(11) 0.0356(11) 0.0023(9) -0.0030(9) 0.0070(10) _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 N3 1.9638(17) . ? Cu1 N1 2.0692(14) . ? Cu1 S1 2.3264(5) . ? Cu1 S1 2.4349(5) 3_666 ? Cu1 Cu1 2.6711(4) 3_666 ? P1 N2 1.6621(14) . ? P1 C12 1.7950(16) . ? P1 C6 1.8017(15) . ? P1 S1 1.9943(5) . ? S1 Cu1 2.4349(4) 3_666 ? N1 C1 1.335(2) . ? N1 C5 1.359(2) . ? N2 C1 1.393(2) . ? N2 H2N 0.8800 . ? N3 C18 1.140(3) . ? C1 C2 1.396(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.368(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C11 1.394(2) . ? C6 C7 1.397(2) . ? C7 C8 1.385(2) . ? C7 H7 0.9500 . ? C8 C9 1.396(3) . ? C8 H8 0.9500 . ? C9 C10 1.381(3) . ? C9 H9 0.9500 . ? C10 C11 1.393(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.391(2) . ? C12 C13 1.391(2) . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.376(3) . ? C15 H15 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.455(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Sb1 F3 1.8721(11) . ? Sb1 F4 1.8728(12) . ? Sb1 F5 1.8734(11) . ? Sb1 F6 1.8740(11) . ? Sb1 F2 1.8761(12) . ? Sb1 F1 1.8783(11) . ? O1 C22 1.414(3) . ? O1 C20 1.436(2) . ? C20 C21 1.505(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.499(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 N3 Cu1 N1 111.59(6) . . ? N3 Cu1 S1 113.12(5) . . ? N1 Cu1 S1 110.14(4) . . ? N3 Cu1 S1 118.98(5) . 3_666 ? N1 Cu1 S1 88.58(4) . 3_666 ? S1 Cu1 S1 111.792(14) . 3_666 ? N3 Cu1 Cu1 141.60(5) . 3_666 ? N1 Cu1 Cu1 106.10(4) . 3_666 ? S1 Cu1 Cu1 57.823(13) . 3_666 ? S1 Cu1 Cu1 53.969(12) 3_666 3_666 ? N2 P1 C12 102.16(7) . . ? N2 P1 C6 107.46(7) . . ? C12 P1 C6 108.63(7) . . ? N2 P1 S1 116.62(5) . . ? C12 P1 S1 110.41(5) . . ? C6 P1 S1 111.01(5) . . ? P1 S1 Cu1 87.491(19) . . ? P1 S1 Cu1 118.96(2) . 3_666 ? Cu1 S1 Cu1 68.208(14) . 3_666 ? C1 N1 C5 117.45(15) . . ? C1 N1 Cu1 125.43(11) . . ? C5 N1 Cu1 114.60(11) . . ? C1 N2 P1 127.66(12) . . ? C1 N2 H2N 116.2 . . ? P1 N2 H2N 116.2 . . ? C18 N3 Cu1 169.34(15) . . ? N1 C1 N2 119.15(14) . . ? N1 C1 C2 122.40(16) . . ? N2 C1 C2 118.45(15) . . ? C3 C2 C1 118.65(18) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.71(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.17(17) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.59(17) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C11 C6 C7 120.10(14) . . ? C11 C6 P1 120.86(12) . . ? C7 C6 P1 119.01(12) . . ? C8 C7 C6 119.83(15) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.88(16) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.45(15) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.99(16) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 119.72(15) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C17 C12 C13 120.08(15) . . ? C17 C12 P1 119.02(12) . . ? C13 C12 P1 120.86(13) . . ? C14 C13 C12 119.34(18) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 120.49(18) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.25(17) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.05(17) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 119.77(16) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N3 C18 C19 179.5(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F3 Sb1 F4 178.86(6) . . ? F3 Sb1 F5 89.40(6) . . ? F4 Sb1 F5 89.69(6) . . ? F3 Sb1 F6 90.03(6) . . ? F4 Sb1 F6 90.87(6) . . ? F5 Sb1 F6 179.28(6) . . ? F3 Sb1 F2 90.31(6) . . ? F4 Sb1 F2 90.39(7) . . ? F5 Sb1 F2 90.18(6) . . ? F6 Sb1 F2 90.26(6) . . ? F3 Sb1 F1 89.57(6) . . ? F4 Sb1 F1 89.73(6) . . ? F5 Sb1 F1 89.95(6) . . ? F6 Sb1 F1 89.60(6) . . ? F2 Sb1 F1 179.82(7) . . ? C22 O1 C20 111.19(16) . . ? O1 C20 C21 109.22(19) . . ? O1 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? O1 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C22 C23 109.52(17) . . ? O1 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? O1 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 N2 P1 S1 Cu1 57.12(6) . . . . ? C12 P1 S1 Cu1 173.09(6) . . . . ? C6 P1 S1 Cu1 -66.38(5) . . . . ? N2 P1 S1 Cu1 -6.20(6) . . . 3_666 ? C12 P1 S1 Cu1 109.77(6) . . . 3_666 ? C6 P1 S1 Cu1 -129.70(5) . . . 3_666 ? N3 Cu1 S1 P1 99.79(5) . . . . ? N1 Cu1 S1 P1 -25.85(4) . . . . ? S1 Cu1 S1 P1 -122.64(2) 3_666 . . . ? Cu1 Cu1 S1 P1 -122.64(2) 3_666 . . . ? N3 Cu1 S1 Cu1 -137.57(5) . . . 3_666 ? N1 Cu1 S1 Cu1 96.79(4) . . . 3_666 ? S1 Cu1 S1 Cu1 0.0 3_666 . . 3_666 ? N3 Cu1 N1 C1 -135.92(13) . . . . ? S1 Cu1 N1 C1 -9.42(14) . . . . ? S1 Cu1 N1 C1 103.32(13) 3_666 . . . ? Cu1 Cu1 N1 C1 51.60(13) 3_666 . . . ? N3 Cu1 N1 C5 62.66(13) . . . . ? S1 Cu1 N1 C5 -170.84(11) . . . . ? S1 Cu1 N1 C5 -58.10(12) 3_666 . . . ? Cu1 Cu1 N1 C5 -109.82(12) 3_666 . . . ? C12 P1 N2 C1 171.31(14) . . . . ? C6 P1 N2 C1 57.09(15) . . . . ? S1 P1 N2 C1 -68.23(15) . . . . ? N1 Cu1 N3 C18 53.9(9) . . . . ? S1 Cu1 N3 C18 -71.0(9) . . . . ? S1 Cu1 N3 C18 154.7(8) 3_666 . . . ? Cu1 Cu1 N3 C18 -137.8(8) 3_666 . . . ? C5 N1 C1 N2 -178.01(14) . . . . ? Cu1 N1 C1 N2 21.0(2) . . . . ? C5 N1 C1 C2 1.7(2) . . . . ? Cu1 N1 C1 C2 -159.20(15) . . . . ? P1 N2 C1 N1 15.3(2) . . . . ? P1 N2 C1 C2 -164.43(15) . . . . ? N1 C1 C2 C3 -2.5(3) . . . . ? N2 C1 C2 C3 177.3(2) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C1 N1 C5 C4 0.0(3) . . . . ? Cu1 N1 C5 C4 162.97(15) . . . . ? C3 C4 C5 N1 -0.9(3) . . . . ? N2 P1 C6 C11 20.41(14) . . . . ? C12 P1 C6 C11 -89.40(13) . . . . ? S1 P1 C6 C11 149.02(11) . . . . ? N2 P1 C6 C7 -161.60(12) . . . . ? C12 P1 C6 C7 88.59(13) . . . . ? S1 P1 C6 C7 -32.99(13) . . . . ? C11 C6 C7 C8 -0.3(2) . . . . ? P1 C6 C7 C8 -178.30(13) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C6 -1.2(2) . . . . ? C7 C6 C11 C10 1.4(2) . . . . ? P1 C6 C11 C10 179.32(12) . . . . ? N2 P1 C12 C17 90.75(14) . . . . ? C6 P1 C12 C17 -155.89(13) . . . . ? S1 P1 C12 C17 -33.94(15) . . . . ? N2 P1 C12 C13 -86.94(17) . . . . ? C6 P1 C12 C13 26.42(18) . . . . ? S1 P1 C12 C13 148.37(15) . . . . ? C17 C12 C13 C14 0.8(3) . . . . ? P1 C12 C13 C14 178.4(2) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C14 C15 C16 -1.6(4) . . . . ? C14 C15 C16 C17 1.4(3) . . . . ? C13 C12 C17 C16 -0.9(3) . . . . ? P1 C12 C17 C16 -178.63(14) . . . . ? C15 C16 C17 C12 -0.2(3) . . . . ? C22 O1 C20 C21 -172.35(18) . . . . ? C20 O1 C22 C23 176.36(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O1 0.88 1.99 2.8677(19) 171.5 . C3 H3 F1 0.95 2.37 3.213(2) 146.9 . C19 H19A F2 0.98 2.45 3.405(2) 166.0 4_576 C19 H19B F3 0.98 2.46 3.394(2) 158.3 2 C19 H19C F4 0.98 2.32 3.259(2) 160.4 2_655 C22 H22A F4 0.99 2.53 3.370(3) 142.6 2_645 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.067 _refine_diff_density_min -1.003 _refine_diff_density_rms 0.068 #===END # 1477 [Cu2(SPN-iPr)2(CH3CN)2](SbF6)2 data_11b-1477 _database_code_depnum_ccdc_archive 'CCDC 810375' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449 #_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1477 (Cu2(SPN-iPr)2(CH3CN)2)(SbF6)2 at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C26 H44 Cu2 N6 P2 S2, 2(F6 Sb)' _chemical_formula_sum 'C26 H44 Cu2 F12 N6 P2 S2 Sb2' _chemical_formula_weight 1165.31 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' Sb Sb -0.5866 1.5461 '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 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 24.901(3) _cell_length_b 12.6741(17) _cell_length_c 16.782(2) _cell_angle_alpha 90.00 _cell_angle_beta 126.3100(10) _cell_angle_gamma 90.00 _cell_volume 4267.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9426 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.07 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 2.488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Large block-like crystals from acetone / diethylether by vapour diffusion. Bruker Kappa APEX-2 CCD diffractometer. SbF6 octahedron orientation disordered with two orientations in 0.853(2) / 0.147(2) proportion. Isotropic displacement parameters for F atoms of subordinate orientation. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 38535 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6224 _reflns_number_gt 5816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0247P)^2^+6.1614P] 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 SHELXL _refine_ls_extinction_coef 0.00010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6224 _refine_ls_number_parameters 270 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0227 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0538 _refine_ls_wR_factor_gt 0.0520 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.002 _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 0.499383(9) 0.602924(14) 0.528144(13) 0.02169(5) Uani 1 1 d . . . S1 S 0.442342(17) 0.46515(3) 0.53529(2) 0.01943(7) Uani 1 1 d . . . P1 P 0.354629(17) 0.52974(3) 0.42874(2) 0.01545(6) Uani 1 1 d . . . N1 N 0.43465(6) 0.68727(9) 0.39679(8) 0.0188(2) Uani 1 1 d . . . N2 N 0.34647(6) 0.56616(9) 0.32621(8) 0.0183(2) Uani 1 1 d . . . H2N H 0.3171 0.5304 0.2723 0.022 Uiso 1 1 calc R . . N3 N 0.54181(7) 0.71440(11) 0.62918(10) 0.0277(3) Uani 1 1 d . . . C1 C 0.38026(7) 0.64598(10) 0.31523(9) 0.0177(2) Uani 1 1 d . . . C2 C 0.35610(8) 0.67912(13) 0.21964(11) 0.0263(3) Uani 1 1 d . . . H2 H 0.3178 0.6473 0.1630 0.032 Uiso 1 1 calc R . . C3 C 0.38942(9) 0.75899(14) 0.20998(12) 0.0319(3) Uani 1 1 d . . . H3 H 0.3747 0.7823 0.1462 0.038 Uiso 1 1 calc R . . C4 C 0.44467(8) 0.80525(13) 0.29423(12) 0.0279(3) Uani 1 1 d . . . H4 H 0.4678 0.8613 0.2891 0.033 Uiso 1 1 calc R . . C5 C 0.46523(7) 0.76803(11) 0.38548(11) 0.0229(3) Uani 1 1 d . . . H5 H 0.5025 0.8005 0.4430 0.028 Uiso 1 1 calc R . . C6 C 0.33829(7) 0.64829(11) 0.47325(10) 0.0192(2) Uani 1 1 d . . . H6 H 0.3638 0.7066 0.4695 0.023 Uiso 1 1 calc R . . C7 C 0.36363(8) 0.64278(13) 0.58170(11) 0.0267(3) Uani 1 1 d . . . H7A H 0.3588 0.7121 0.6027 0.040 Uiso 1 1 calc R . . H7B H 0.4107 0.6222 0.6232 0.040 Uiso 1 1 calc R . . H7C H 0.3376 0.5905 0.5885 0.040 Uiso 1 1 calc R . . C8 C 0.26459(7) 0.67991(12) 0.40393(11) 0.0247(3) Uani 1 1 d . . . H8A H 0.2381 0.6319 0.4136 0.037 Uiso 1 1 calc R . . H8B H 0.2494 0.6758 0.3352 0.037 Uiso 1 1 calc R . . H8C H 0.2592 0.7523 0.4188 0.037 Uiso 1 1 calc R . . C9 C 0.28805(7) 0.43270(11) 0.37992(10) 0.0198(2) Uani 1 1 d . . . H9 H 0.2451 0.4664 0.3257 0.024 Uiso 1 1 calc R . . C10 C 0.28201(9) 0.39787(13) 0.46172(12) 0.0275(3) Uani 1 1 d . . . H10A H 0.2481 0.3426 0.4363 0.041 Uiso 1 1 calc R . . H10B H 0.2691 0.4584 0.4833 0.041 Uiso 1 1 calc R . . H10C H 0.3250 0.3704 0.5179 0.041 Uiso 1 1 calc R . . C11 C 0.30093(8) 0.33711(11) 0.33725(11) 0.0251(3) Uani 1 1 d . . . H11A H 0.3420 0.3016 0.3902 0.038 Uiso 1 1 calc R . . H11B H 0.3056 0.3608 0.2861 0.038 Uiso 1 1 calc R . . H11C H 0.2634 0.2879 0.3083 0.038 Uiso 1 1 calc R . . C12 C 0.55457(8) 0.79361(14) 0.66845(11) 0.0270(3) Uani 1 1 d . . . C13 C 0.56924(10) 0.89598(15) 0.71653(14) 0.0370(4) Uani 1 1 d . . . H13A H 0.6118 0.9221 0.7332 0.055 Uiso 1 1 calc R . . H13B H 0.5721 0.8889 0.7771 0.055 Uiso 1 1 calc R . . H13C H 0.5337 0.9459 0.6717 0.055 Uiso 1 1 calc R . . Sb1 Sb 0.152083(12) 0.498962(19) 0.05339(3) 0.02077(6) Uani 0.8528(16) 1 d P A 1 F1 F 0.24515(6) 0.48141(11) 0.12275(10) 0.0353(3) Uani 0.8528(16) 1 d P A 1 F2 F 0.06107(8) 0.51751(16) -0.01223(16) 0.0708(6) Uani 0.8528(16) 1 d P A 1 F3 F 0.16999(8) 0.57909(10) 0.16058(10) 0.0420(3) Uani 0.8528(16) 1 d P A 1 F4 F 0.13923(10) 0.41830(14) -0.04934(11) 0.0631(5) Uani 0.8528(16) 1 d P A 1 F5 F 0.15139(7) 0.37776(10) 0.11653(12) 0.0409(3) Uani 0.8528(16) 1 d P A 1 F6 F 0.15733(11) 0.62133(14) -0.00392(14) 0.0585(5) Uani 0.8528(16) 1 d P A 1 Sb1' Sb 0.13972(8) 0.51227(8) 0.01848(17) 0.0160(3) Uani 0.1472(16) 1 d PD A 2 F1' F 0.2110(3) 0.4861(5) 0.1512(5) 0.0363(9) Uiso 0.1472(16) 1 d PD A 2 F2' F 0.0688(3) 0.5388(6) -0.1126(4) 0.0363(9) Uiso 0.1472(16) 1 d PD A 2 F3' F 0.0975(3) 0.5935(5) 0.0603(5) 0.0363(9) Uiso 0.1472(16) 1 d PD A 2 F4' F 0.1816(4) 0.4291(5) -0.0212(5) 0.0363(9) Uiso 0.1472(16) 1 d PD A 2 F5' F 0.0964(3) 0.3911(5) 0.0193(5) 0.0363(9) Uiso 0.1472(16) 1 d PD A 2 F6' F 0.1840(4) 0.6313(7) 0.0207(7) 0.0363(9) Uiso 0.1472(16) 1 d PD 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 0.02273(9) 0.02102(9) 0.01781(8) 0.00134(6) 0.01008(7) 0.00259(6) S1 0.02137(15) 0.02025(15) 0.01639(14) 0.00474(11) 0.01103(12) 0.00598(12) P1 0.01897(15) 0.01418(14) 0.01416(13) 0.00139(11) 0.01034(12) 0.00270(11) N1 0.0209(5) 0.0166(5) 0.0203(5) 0.0030(4) 0.0130(4) 0.0043(4) N2 0.0220(5) 0.0185(5) 0.0140(5) 0.0011(4) 0.0105(4) 0.0003(4) N3 0.0288(6) 0.0313(7) 0.0217(6) -0.0029(5) 0.0142(5) 0.0012(5) C1 0.0220(6) 0.0169(6) 0.0178(5) 0.0035(4) 0.0138(5) 0.0054(5) C2 0.0316(7) 0.0298(8) 0.0175(6) 0.0036(5) 0.0146(6) 0.0007(6) C3 0.0435(9) 0.0331(8) 0.0268(7) 0.0084(6) 0.0250(7) 0.0020(7) C4 0.0350(8) 0.0241(7) 0.0346(8) 0.0066(6) 0.0262(7) 0.0025(6) C5 0.0244(6) 0.0192(6) 0.0282(7) 0.0022(5) 0.0171(6) 0.0023(5) C6 0.0230(6) 0.0163(6) 0.0214(6) -0.0009(4) 0.0148(5) 0.0020(5) C7 0.0323(7) 0.0280(7) 0.0237(7) -0.0043(5) 0.0188(6) 0.0024(6) C8 0.0257(7) 0.0209(6) 0.0298(7) 0.0020(5) 0.0177(6) 0.0059(5) C9 0.0242(6) 0.0167(6) 0.0193(6) 0.0002(5) 0.0133(5) -0.0003(5) C10 0.0369(8) 0.0244(7) 0.0293(7) -0.0011(6) 0.0241(7) -0.0052(6) C11 0.0334(7) 0.0181(6) 0.0255(7) -0.0033(5) 0.0183(6) -0.0015(5) C12 0.0259(7) 0.0332(8) 0.0207(6) -0.0030(6) 0.0132(6) 0.0013(6) C13 0.0424(9) 0.0343(9) 0.0325(8) -0.0113(7) 0.0212(8) -0.0023(7) Sb1 0.02294(8) 0.01915(8) 0.01859(12) -0.00070(7) 0.01140(8) 0.00175(5) F1 0.0251(6) 0.0456(7) 0.0346(6) 0.0032(5) 0.0173(5) -0.0020(5) F2 0.0263(7) 0.0767(12) 0.0785(13) 0.0036(10) 0.0142(8) 0.0174(7) F3 0.0730(10) 0.0282(6) 0.0397(7) -0.0055(5) 0.0416(7) -0.0005(6) F4 0.0778(12) 0.0618(10) 0.0256(7) -0.0170(7) 0.0174(7) 0.0143(9) F5 0.0481(7) 0.0220(6) 0.0647(9) 0.0037(6) 0.0400(7) -0.0051(5) F6 0.1048(16) 0.0395(8) 0.0569(12) 0.0278(8) 0.0620(12) 0.0234(10) Sb1' 0.0246(5) 0.0142(3) 0.0136(6) 0.0035(3) 0.0136(5) 0.0027(3) _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 N3 1.9661(14) . ? Cu1 N1 2.0957(11) . ? Cu1 S1 2.2984(5) . ? Cu1 S1 2.4110(4) 5_666 ? Cu1 Cu1 2.7810(5) 5_666 ? S1 P1 2.0032(5) . ? S1 Cu1 2.4110(4) 5_666 ? P1 N2 1.6735(12) . ? P1 C9 1.8231(15) . ? P1 C6 1.8278(14) . ? N1 C1 1.3365(18) . ? N1 C5 1.3545(18) . ? N2 C1 1.3961(18) . ? N2 H2N 0.8800 . ? N3 C12 1.138(2) . ? C1 C2 1.4031(18) . ? C2 C3 1.378(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.379(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C8 1.534(2) . ? C6 C7 1.535(2) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.532(2) . ? C9 C11 1.535(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.456(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? Sb1 F2 1.8569(16) . ? Sb1 F4 1.8618(14) . ? Sb1 F6 1.8698(16) . ? Sb1 F5 1.8720(13) . ? Sb1 F3 1.8751(12) . ? Sb1 F1 1.8922(13) . ? Sb1' F6' 1.857(7) . ? Sb1' F4' 1.862(6) . ? Sb1' F2' 1.863(6) . ? Sb1' F3' 1.879(6) . ? Sb1' F1' 1.881(7) . ? Sb1' F5' 1.882(6) . ? 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 N3 Cu1 N1 103.08(5) . . ? N3 Cu1 S1 122.28(4) . . ? N1 Cu1 S1 109.16(4) . . ? N3 Cu1 S1 118.77(4) . 5_666 ? N1 Cu1 S1 90.42(3) . 5_666 ? S1 Cu1 S1 107.655(14) . 5_666 ? N3 Cu1 Cu1 149.17(4) . 5_666 ? N1 Cu1 Cu1 106.12(3) . 5_666 ? S1 Cu1 Cu1 55.701(13) . 5_666 ? S1 Cu1 Cu1 51.955(11) 5_666 5_666 ? P1 S1 Cu1 91.366(19) . . ? P1 S1 Cu1 112.04(2) . 5_666 ? Cu1 S1 Cu1 72.345(14) . 5_666 ? N2 P1 C9 101.51(6) . . ? N2 P1 C6 105.82(6) . . ? C9 P1 C6 112.02(7) . . ? N2 P1 S1 115.78(5) . . ? C9 P1 S1 110.26(5) . . ? C6 P1 S1 111.10(5) . . ? C1 N1 C5 117.73(12) . . ? C1 N1 Cu1 124.01(9) . . ? C5 N1 Cu1 112.76(9) . . ? C1 N2 P1 128.30(9) . . ? C1 N2 H2N 115.8 . . ? P1 N2 H2N 115.8 . . ? C12 N3 Cu1 163.03(13) . . ? N1 C1 N2 118.24(11) . . ? N1 C1 C2 122.82(13) . . ? N2 C1 C2 118.94(13) . . ? C3 C2 C1 118.29(15) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 119.51(14) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.56(14) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.99(14) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C8 C6 C7 112.22(12) . . ? C8 C6 P1 111.14(10) . . ? C7 C6 P1 114.36(10) . . ? C8 C6 H6 106.1 . . ? C7 C6 H6 106.1 . . ? P1 C6 H6 106.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 110.43(12) . . ? C10 C9 P1 109.72(10) . . ? C11 C9 P1 110.89(10) . . ? C10 C9 H9 108.6 . . ? C11 C9 H9 108.6 . . ? P1 C9 H9 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 178.5(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F2 Sb1 F4 92.29(10) . . ? F2 Sb1 F6 91.28(10) . . ? F4 Sb1 F6 90.30(9) . . ? F2 Sb1 F5 91.29(8) . . ? F4 Sb1 F5 91.11(8) . . ? F6 Sb1 F5 177.01(9) . . ? F2 Sb1 F3 90.79(9) . . ? F4 Sb1 F3 176.91(8) . . ? F6 Sb1 F3 89.71(7) . . ? F5 Sb1 F3 88.74(6) . . ? F2 Sb1 F1 178.76(8) . . ? F4 Sb1 F1 88.94(8) . . ? F6 Sb1 F1 88.90(8) . . ? F5 Sb1 F1 88.50(6) . . ? F3 Sb1 F1 87.98(7) . . ? F6' Sb1' F4' 90.9(3) . . ? F6' Sb1' F2' 90.8(3) . . ? F4' Sb1' F2' 91.1(3) . . ? F6' Sb1' F3' 90.3(3) . . ? F4' Sb1' F3' 178.7(3) . . ? F2' Sb1' F3' 89.6(3) . . ? F6' Sb1' F1' 89.2(3) . . ? F4' Sb1' F1' 89.3(3) . . ? F2' Sb1' F1' 179.6(3) . . ? F3' Sb1' F1' 90.0(3) . . ? F6' Sb1' F5' 178.7(4) . . ? F4' Sb1' F5' 89.2(3) . . ? F2' Sb1' F5' 90.5(3) . . ? F3' Sb1' F5' 89.7(3) . . ? F1' Sb1' F5' 89.5(3) . . ? 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 Cu1 S1 P1 104.28(5) . . . . ? N1 Cu1 S1 P1 -15.91(4) . . . . ? S1 Cu1 S1 P1 -112.730(19) 5_666 . . . ? Cu1 Cu1 S1 P1 -112.730(19) 5_666 . . . ? N3 Cu1 S1 Cu1 -142.99(5) . . . 5_666 ? N1 Cu1 S1 Cu1 96.82(4) . . . 5_666 ? S1 Cu1 S1 Cu1 0.0 5_666 . . 5_666 ? Cu1 S1 P1 N2 50.64(5) . . . . ? Cu1 S1 P1 N2 -20.84(5) 5_666 . . . ? Cu1 S1 P1 C9 165.11(5) . . . . ? Cu1 S1 P1 C9 93.63(5) 5_666 . . . ? Cu1 S1 P1 C6 -70.08(5) . . . . ? Cu1 S1 P1 C6 -141.56(5) 5_666 . . . ? N3 Cu1 N1 C1 -156.26(11) . . . . ? S1 Cu1 N1 C1 -24.87(11) . . . . ? S1 Cu1 N1 C1 84.01(10) 5_666 . . . ? Cu1 Cu1 N1 C1 33.76(11) 5_666 . . . ? N3 Cu1 N1 C5 50.66(11) . . . . ? S1 Cu1 N1 C5 -177.95(9) . . . . ? S1 Cu1 N1 C5 -69.07(9) 5_666 . . . ? Cu1 Cu1 N1 C5 -119.32(9) 5_666 . . . ? C9 P1 N2 C1 173.91(12) . . . . ? C6 P1 N2 C1 56.81(13) . . . . ? S1 P1 N2 C1 -66.71(13) . . . . ? N1 Cu1 N3 C12 9.6(5) . . . . ? S1 Cu1 N3 C12 -113.5(5) . . . . ? S1 Cu1 N3 C12 107.4(5) 5_666 . . . ? Cu1 Cu1 N3 C12 170.5(4) 5_666 . . . ? C5 N1 C1 N2 -176.95(12) . . . . ? Cu1 N1 C1 N2 31.20(16) . . . . ? C5 N1 C1 C2 3.3(2) . . . . ? Cu1 N1 C1 C2 -148.52(12) . . . . ? P1 N2 C1 N1 14.09(18) . . . . ? P1 N2 C1 C2 -166.19(11) . . . . ? N1 C1 C2 C3 -1.2(2) . . . . ? N2 C1 C2 C3 179.10(14) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C1 N1 C5 C4 -3.3(2) . . . . ? Cu1 N1 C5 C4 151.62(12) . . . . ? C3 C4 C5 N1 1.1(2) . . . . ? N2 P1 C6 C8 69.63(11) . . . . ? C9 P1 C6 C8 -40.14(12) . . . . ? S1 P1 C6 C8 -163.95(9) . . . . ? N2 P1 C6 C7 -162.03(10) . . . . ? C9 P1 C6 C7 88.20(12) . . . . ? S1 P1 C6 C7 -35.61(12) . . . . ? N2 P1 C9 C10 -173.75(10) . . . . ? C6 P1 C9 C10 -61.27(12) . . . . ? S1 P1 C9 C10 63.01(11) . . . . ? N2 P1 C9 C11 64.00(11) . . . . ? C6 P1 C9 C11 176.48(9) . . . . ? S1 P1 C9 C11 -59.24(10) . . . . ? Cu1 N3 C12 C13 14(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N F1 0.88 2.14 2.9958(18) 164.8 . N2 H2N F1' 0.88 2.25 3.049(7) 150.8 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.794 _refine_diff_density_min -0.689 _refine_diff_density_rms 0.065 #===END # 1505 [Cu2(SPN-iPr)2(CN-tBu)2](SbF6)2.2(Et2O) data_12-1505 _database_code_depnum_ccdc_archive 'CCDC 810376' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449 #_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1505 (Cu2(SPN-iPr)2(CN-tBu)2)(SbF6)2.2(Et2O) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C32 H56 Cu2 N6 P2 S2, 2(C4 H10 O), 2(F6 Sb)' _chemical_formula_sum 'C40 H76 Cu2 F12 N6 O2 P2 S2 Sb2' _chemical_formula_weight 1397.71 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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.3328(5) _cell_length_b 14.0819(6) _cell_length_c 16.0780(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.539(2) _cell_angle_gamma 90.00 _cell_volume 2957.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9714 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 1.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from dichloromethane / diethyl ether by vapour diffusion. Bruker Kappa APEX-2 CCD diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 70429 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8606 _reflns_number_gt 8040 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0169P)^2^+1.4001P] 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 8606 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0187 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0420 _refine_ls_wR_factor_gt 0.0404 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.006 _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 0.454676(11) 0.478704(10) 0.404487(9) 0.01905(3) Uani 1 1 d . . . S1 S 0.39353(2) 0.580159(18) 0.500071(17) 0.01686(5) Uani 1 1 d . . . P1 P 0.27326(2) 0.495809(19) 0.500681(17) 0.01378(5) Uani 1 1 d . . . N1 N 0.38340(7) 0.34744(7) 0.41177(6) 0.01746(17) Uani 1 1 d . . . N2 N 0.30228(7) 0.38215(6) 0.52473(6) 0.01485(16) Uani 1 1 d . . . H2N H 0.2884 0.3616 0.5729 0.018 Uiso 1 1 calc R . . N3 N 0.46005(8) 0.55867(7) 0.23009(6) 0.02243(19) Uani 1 1 d . . . C1 C 0.34564(8) 0.31624(7) 0.47798(7) 0.01532(18) Uani 1 1 d . . . C2 C 0.34758(9) 0.22010(8) 0.50141(8) 0.0226(2) Uani 1 1 d . . . H2 H 0.3225 0.2005 0.5500 0.027 Uiso 1 1 calc R . . C3 C 0.38683(10) 0.15462(9) 0.45231(9) 0.0281(3) Uani 1 1 d . . . H3 H 0.3899 0.0892 0.4670 0.034 Uiso 1 1 calc R . . C4 C 0.42186(10) 0.18593(9) 0.38092(8) 0.0264(2) Uani 1 1 d . . . H4 H 0.4472 0.1421 0.3452 0.032 Uiso 1 1 calc R . . C5 C 0.41895(9) 0.28143(9) 0.36318(8) 0.0225(2) Uani 1 1 d . . . H5 H 0.4430 0.3024 0.3145 0.027 Uiso 1 1 calc R . . C6 C 0.18845(8) 0.49402(8) 0.39618(7) 0.0198(2) Uani 1 1 d . . . H6 H 0.2175 0.4462 0.3616 0.024 Uiso 1 1 calc R . . C7 C 0.18476(10) 0.58843(10) 0.34841(8) 0.0280(3) Uani 1 1 d . . . H7A H 0.1410 0.5817 0.2920 0.042 Uiso 1 1 calc R . . H7B H 0.2541 0.6061 0.3425 0.042 Uiso 1 1 calc R . . H7C H 0.1568 0.6379 0.3802 0.042 Uiso 1 1 calc R . . C8 C 0.08145(9) 0.45813(9) 0.40241(8) 0.0241(2) Uani 1 1 d . . . H8A H 0.0463 0.5066 0.4297 0.036 Uiso 1 1 calc R . . H8B H 0.0879 0.3997 0.4362 0.036 Uiso 1 1 calc R . . H8C H 0.0419 0.4451 0.3453 0.036 Uiso 1 1 calc R . . C9 C 0.20433(8) 0.52998(8) 0.58300(7) 0.01806(19) Uani 1 1 d . . . H9 H 0.1437 0.4872 0.5790 0.022 Uiso 1 1 calc R . . C10 C 0.16542(10) 0.63249(9) 0.56882(9) 0.0266(2) Uani 1 1 d . . . H10A H 0.1287 0.6502 0.6136 0.040 Uiso 1 1 calc R . . H10B H 0.1191 0.6373 0.5134 0.040 Uiso 1 1 calc R . . H10C H 0.2237 0.6754 0.5705 0.040 Uiso 1 1 calc R . . C11 C 0.27145(9) 0.51879(8) 0.67156(7) 0.0224(2) Uani 1 1 d . . . H11A H 0.3327 0.5585 0.6761 0.034 Uiso 1 1 calc R . . H11B H 0.2919 0.4522 0.6809 0.034 Uiso 1 1 calc R . . H11C H 0.2328 0.5385 0.7144 0.034 Uiso 1 1 calc R . . C12 C 0.46019(9) 0.52651(9) 0.29583(8) 0.0224(2) Uani 1 1 d . . . C13 C 0.45553(10) 0.60470(8) 0.14795(7) 0.0219(2) Uani 1 1 d . . . C14 C 0.39778(12) 0.69790(10) 0.15094(9) 0.0338(3) Uani 1 1 d . . . H14A H 0.3297 0.6846 0.1624 0.051 Uiso 1 1 calc R . . H14B H 0.3908 0.7306 0.0963 0.051 Uiso 1 1 calc R . . H14C H 0.4358 0.7383 0.1961 0.051 Uiso 1 1 calc R . . C15 C 0.39946(11) 0.53830(10) 0.07968(8) 0.0303(3) Uani 1 1 d . . . H15A H 0.4363 0.4778 0.0824 0.045 Uiso 1 1 calc R . . H15B H 0.3959 0.5672 0.0237 0.045 Uiso 1 1 calc R . . H15C H 0.3300 0.5270 0.0889 0.045 Uiso 1 1 calc R . . C16 C 0.56516(11) 0.62206(10) 0.13713(9) 0.0295(3) Uani 1 1 d . . . H16A H 0.6006 0.6623 0.1835 0.044 Uiso 1 1 calc R . . H16B H 0.5642 0.6538 0.0827 0.044 Uiso 1 1 calc R . . H16C H 0.6010 0.5612 0.1382 0.044 Uiso 1 1 calc R . . Sb1 Sb 0.100942(6) 0.245872(5) 0.661962(4) 0.01659(2) Uani 1 1 d . . . F1 F 0.23880(6) 0.28094(6) 0.66603(5) 0.02698(15) Uani 1 1 d . . . F2 F -0.03551(6) 0.21035(6) 0.65622(6) 0.03605(19) Uani 1 1 d . . . F3 F 0.07490(8) 0.26863(7) 0.54478(5) 0.0392(2) Uani 1 1 d . . . F4 F 0.12951(7) 0.22765(6) 0.77924(5) 0.02914(16) Uani 1 1 d . . . F5 F 0.06938(6) 0.37303(5) 0.67871(6) 0.03059(17) Uani 1 1 d . . . F6 F 0.13522(7) 0.12019(5) 0.64254(5) 0.03141(17) Uani 1 1 d . . . O1 O 0.33711(8) -0.08222(6) 0.46784(6) 0.02919(19) Uani 1 1 d . . . C17 C 0.31167(15) -0.15169(11) 0.40284(11) 0.0411(3) Uani 1 1 d . . . H17A H 0.2391 -0.1707 0.3968 0.049 Uiso 1 1 calc R . . H17B H 0.3549 -0.2088 0.4175 0.049 Uiso 1 1 calc R . . C18 C 0.3293(2) -0.10968(16) 0.32102(12) 0.0661(6) Uani 1 1 d . . . H18A H 0.2891 -0.0513 0.3086 0.099 Uiso 1 1 calc R . . H18B H 0.3082 -0.1553 0.2748 0.099 Uiso 1 1 calc R . . H18C H 0.4022 -0.0950 0.3263 0.099 Uiso 1 1 calc R . . C19 C 0.31639(11) -0.11478(10) 0.54590(9) 0.0317(3) Uani 1 1 d . . . H19A H 0.3581 -0.1718 0.5650 0.038 Uiso 1 1 calc R . . H19B H 0.2432 -0.1323 0.5387 0.038 Uiso 1 1 calc R . . C20 C 0.34160(16) -0.03731(13) 0.61080(11) 0.0487(4) Uani 1 1 d . . . H20A H 0.4127 -0.0172 0.6146 0.073 Uiso 1 1 calc R . . H20B H 0.3327 -0.0610 0.6662 0.073 Uiso 1 1 calc R . . H20C H 0.2958 0.0168 0.5940 0.073 Uiso 1 1 calc 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 0.01881(6) 0.02161(7) 0.01812(6) 0.00557(5) 0.00706(5) -0.00082(5) S1 0.01439(11) 0.01474(11) 0.02199(12) 0.00346(9) 0.00491(9) -0.00114(9) P1 0.01245(11) 0.01279(11) 0.01657(12) 0.00193(9) 0.00407(9) 0.00053(9) N1 0.0164(4) 0.0198(4) 0.0171(4) -0.0019(3) 0.0057(3) -0.0015(3) N2 0.0178(4) 0.0126(4) 0.0158(4) 0.0020(3) 0.0073(3) 0.0012(3) N3 0.0238(5) 0.0231(5) 0.0218(5) 0.0059(4) 0.0078(4) 0.0009(4) C1 0.0134(4) 0.0155(4) 0.0173(5) -0.0013(4) 0.0038(4) -0.0007(3) C2 0.0268(6) 0.0157(5) 0.0274(6) 0.0005(4) 0.0104(5) -0.0003(4) C3 0.0327(6) 0.0168(5) 0.0363(7) -0.0044(5) 0.0106(5) 0.0011(5) C4 0.0247(6) 0.0261(6) 0.0297(6) -0.0113(5) 0.0088(5) 0.0006(5) C5 0.0197(5) 0.0287(6) 0.0209(5) -0.0059(4) 0.0084(4) -0.0014(4) C6 0.0168(5) 0.0224(5) 0.0194(5) 0.0038(4) 0.0013(4) 0.0020(4) C7 0.0225(6) 0.0322(6) 0.0278(6) 0.0139(5) 0.0016(5) 0.0018(5) C8 0.0173(5) 0.0248(5) 0.0280(6) 0.0032(5) -0.0007(4) -0.0020(4) C9 0.0162(5) 0.0157(5) 0.0240(5) -0.0015(4) 0.0083(4) -0.0003(4) C10 0.0242(6) 0.0177(5) 0.0404(7) -0.0018(5) 0.0124(5) 0.0041(4) C11 0.0256(5) 0.0224(5) 0.0207(5) -0.0058(4) 0.0084(4) -0.0027(4) C12 0.0204(5) 0.0248(5) 0.0236(5) 0.0053(4) 0.0078(4) 0.0013(4) C13 0.0287(6) 0.0204(5) 0.0179(5) 0.0064(4) 0.0076(4) 0.0007(4) C14 0.0465(8) 0.0268(6) 0.0297(6) 0.0079(5) 0.0115(6) 0.0110(6) C15 0.0374(7) 0.0294(6) 0.0234(6) 0.0023(5) 0.0046(5) -0.0039(5) C16 0.0314(6) 0.0309(6) 0.0288(6) 0.0075(5) 0.0125(5) -0.0050(5) Sb1 0.01994(4) 0.01471(4) 0.01631(4) 0.00282(2) 0.00648(3) 0.00126(2) F1 0.0225(3) 0.0298(4) 0.0309(4) 0.0043(3) 0.0108(3) -0.0011(3) F2 0.0234(4) 0.0321(4) 0.0537(5) 0.0000(4) 0.0102(4) -0.0056(3) F3 0.0493(5) 0.0483(5) 0.0181(4) 0.0084(3) 0.0023(3) 0.0021(4) F4 0.0424(5) 0.0300(4) 0.0175(3) 0.0042(3) 0.0120(3) 0.0048(3) F5 0.0311(4) 0.0164(3) 0.0444(5) 0.0023(3) 0.0080(3) 0.0058(3) F6 0.0421(5) 0.0192(3) 0.0336(4) -0.0053(3) 0.0093(3) 0.0053(3) O1 0.0366(5) 0.0207(4) 0.0329(5) 0.0024(4) 0.0133(4) -0.0005(4) C17 0.0554(10) 0.0247(7) 0.0431(8) -0.0032(6) 0.0095(7) 0.0017(6) C18 0.112(2) 0.0522(11) 0.0396(10) -0.0049(8) 0.0289(11) 0.0141(12) C19 0.0319(7) 0.0309(7) 0.0346(7) 0.0116(5) 0.0121(5) 0.0059(5) C20 0.0670(12) 0.0455(9) 0.0337(8) 0.0056(7) 0.0103(8) 0.0227(8) _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 C12 1.8873(12) . ? Cu1 N1 2.0924(10) . ? Cu1 S1 2.3598(3) . ? Cu1 S1 2.4280(3) 3_666 ? S1 P1 1.9971(4) . ? S1 Cu1 2.4280(3) 3_666 ? P1 N2 1.6736(9) . ? P1 C9 1.8206(11) . ? P1 C6 1.8281(11) . ? N1 C1 1.3394(13) . ? N1 C5 1.3592(14) . ? N2 C1 1.3908(13) . ? N2 H2N 0.8800 . ? N3 C12 1.1496(15) . ? N3 C13 1.4615(14) . ? C1 C2 1.4041(15) . ? C2 C3 1.3830(17) . ? C2 H2 0.9500 . ? C3 C4 1.3945(19) . ? C3 H3 0.9500 . ? C4 C5 1.3737(18) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.5313(16) . ? C6 C8 1.5355(16) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.5308(16) . ? C9 C10 1.5354(16) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 C15 1.5199(18) . ? C13 C16 1.5258(18) . ? C13 C14 1.5271(18) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Sb1 F4 1.8652(7) . ? Sb1 F6 1.8698(7) . ? Sb1 F2 1.8712(8) . ? Sb1 F5 1.8712(7) . ? Sb1 F3 1.8739(8) . ? Sb1 F1 1.8916(7) . ? O1 C19 1.4142(16) . ? O1 C17 1.4221(18) . ? C17 C18 1.503(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.501(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C12 Cu1 N1 117.98(5) . . ? C12 Cu1 S1 117.99(4) . . ? N1 Cu1 S1 106.17(3) . . ? C12 Cu1 S1 121.66(4) . 3_666 ? N1 Cu1 S1 89.63(3) . 3_666 ? S1 Cu1 S1 98.510(10) . 3_666 ? P1 S1 Cu1 91.457(13) . . ? P1 S1 Cu1 111.249(14) . 3_666 ? Cu1 S1 Cu1 81.490(10) . 3_666 ? N2 P1 C9 102.23(5) . . ? N2 P1 C6 105.72(5) . . ? C9 P1 C6 111.24(5) . . ? N2 P1 S1 114.91(3) . . ? C9 P1 S1 111.65(4) . . ? C6 P1 S1 110.69(4) . . ? C1 N1 C5 117.53(10) . . ? C1 N1 Cu1 125.55(7) . . ? C5 N1 Cu1 110.94(7) . . ? C1 N2 P1 127.97(7) . . ? C1 N2 H2N 116.0 . . ? P1 N2 H2N 116.0 . . ? C12 N3 C13 176.15(12) . . ? N1 C1 N2 118.26(9) . . ? N1 C1 C2 122.67(10) . . ? N2 C1 C2 119.06(10) . . ? C3 C2 C1 118.59(11) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.10(12) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.70(11) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 123.29(11) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C7 C6 C8 112.42(9) . . ? C7 C6 P1 113.64(9) . . ? C8 C6 P1 110.89(8) . . ? C7 C6 H6 106.4 . . ? C8 C6 H6 106.4 . . ? P1 C6 H6 106.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 110.62(10) . . ? C11 C9 P1 111.27(8) . . ? C10 C9 P1 110.20(8) . . ? C11 C9 H9 108.2 . . ? C10 C9 H9 108.2 . . ? P1 C9 H9 108.2 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 Cu1 176.76(11) . . ? N3 C13 C15 107.76(10) . . ? N3 C13 C16 107.87(10) . . ? C15 C13 C16 111.12(11) . . ? N3 C13 C14 106.42(10) . . ? C15 C13 C14 111.91(11) . . ? C16 C13 C14 111.49(11) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? F4 Sb1 F6 91.79(4) . . ? F4 Sb1 F2 90.75(4) . . ? F6 Sb1 F2 90.37(4) . . ? F4 Sb1 F5 89.57(4) . . ? F6 Sb1 F5 178.02(4) . . ? F2 Sb1 F5 91.06(4) . . ? F4 Sb1 F3 177.81(4) . . ? F6 Sb1 F3 89.79(4) . . ? F2 Sb1 F3 90.76(4) . . ? F5 Sb1 F3 88.81(4) . . ? F4 Sb1 F1 90.03(4) . . ? F6 Sb1 F1 89.12(4) . . ? F2 Sb1 F1 179.09(4) . . ? F5 Sb1 F1 89.44(4) . . ? F3 Sb1 F1 88.48(4) . . ? C19 O1 C17 111.65(11) . . ? O1 C17 C18 108.44(14) . . ? O1 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O1 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? 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 . . ? O1 C19 C20 108.96(12) . . ? O1 C19 H19A 109.9 . . ? C20 C19 H19A 109.9 . . ? O1 C19 H19B 109.9 . . ? C20 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? 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 . . ? 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 C12 Cu1 S1 P1 115.84(4) . . . . ? N1 Cu1 S1 P1 -19.17(3) . . . . ? S1 Cu1 S1 P1 -111.270(14) 3_666 . . . ? C12 Cu1 S1 Cu1 -132.89(4) . . . 3_666 ? N1 Cu1 S1 Cu1 92.10(3) . . . 3_666 ? S1 Cu1 S1 Cu1 0.0 3_666 . . 3_666 ? Cu1 S1 P1 N2 53.97(4) . . . . ? Cu1 S1 P1 N2 -27.46(4) 3_666 . . . ? Cu1 S1 P1 C9 169.80(4) . . . . ? Cu1 S1 P1 C9 88.36(4) 3_666 . . . ? Cu1 S1 P1 C6 -65.68(4) . . . . ? Cu1 S1 P1 C6 -147.12(4) 3_666 . . . ? C12 Cu1 N1 C1 -158.90(9) . . . . ? S1 Cu1 N1 C1 -23.88(9) . . . . ? S1 Cu1 N1 C1 74.88(9) 3_666 . . . ? C12 Cu1 N1 C5 49.24(9) . . . . ? S1 Cu1 N1 C5 -175.74(7) . . . . ? S1 Cu1 N1 C5 -76.98(8) 3_666 . . . ? C9 P1 N2 C1 172.44(9) . . . . ? C6 P1 N2 C1 55.94(10) . . . . ? S1 P1 N2 C1 -66.44(10) . . . . ? C5 N1 C1 N2 -175.48(10) . . . . ? Cu1 N1 C1 N2 34.30(14) . . . . ? C5 N1 C1 C2 4.07(16) . . . . ? Cu1 N1 C1 C2 -146.14(9) . . . . ? P1 N2 C1 N1 10.67(15) . . . . ? P1 N2 C1 C2 -168.90(9) . . . . ? N1 C1 C2 C3 -2.32(18) . . . . ? N2 C1 C2 C3 177.23(11) . . . . ? C1 C2 C3 C4 -0.77(19) . . . . ? C2 C3 C4 C5 1.9(2) . . . . ? C1 N1 C5 C4 -2.87(17) . . . . ? Cu1 N1 C5 C4 151.49(10) . . . . ? C3 C4 C5 N1 -0.08(19) . . . . ? N2 P1 C6 C7 -158.47(8) . . . . ? C9 P1 C6 C7 91.32(9) . . . . ? S1 P1 C6 C7 -33.43(10) . . . . ? N2 P1 C6 C8 73.75(9) . . . . ? C9 P1 C6 C8 -36.46(10) . . . . ? S1 P1 C6 C8 -161.21(7) . . . . ? N2 P1 C9 C11 60.01(8) . . . . ? C6 P1 C9 C11 172.45(8) . . . . ? S1 P1 C9 C11 -63.34(8) . . . . ? N2 P1 C9 C10 -176.91(8) . . . . ? C6 P1 C9 C10 -64.47(9) . . . . ? S1 P1 C9 C10 59.74(9) . . . . ? C19 O1 C17 C18 176.38(15) . . . . ? C17 O1 C19 C20 -178.18(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N F1 0.88 2.09 2.9459(11) 164.1 . C2 H2 F1 0.95 2.62 3.3732(14) 136.9 . C11 H11B F1 0.98 2.51 3.3763(14) 147.2 . C3 H3 O1 0.95 2.52 3.4192(16) 159.1 . C7 H7B S1 0.98 2.85 3.3154(13) 110.0 . C11 H11A F4 0.98 2.51 3.2561(14) 132.8 2_556 C14 H14B F3 0.98 2.46 3.3890(17) 158.0 2 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.523 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.053 #===END # 1512 [Cu(CF3SO3)(SPN-iPr)(PPh3)] data_13-1512 _database_code_depnum_ccdc_archive 'CCDC 810377' #TrackingRef '- CuEJIC15comps_1a463_1b462_2a457_2b475_3a442_3b449 #_5b480_6b459_7a528_7b529_8b476_11a499_11b477_12-505_13-512.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1512 (Cu(CF3SO3)(SPN-iPr)(PPh3)) at 100K' _chemical_melting_point ? _chemical_formula_moiety 'C30 H34 Cu F3 N2 O3 P2 S2' _chemical_formula_sum 'C30 H34 Cu F3 N2 O3 P2 S2' _chemical_formula_weight 717.19 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.29990(10) _cell_length_b 9.89070(10) _cell_length_c 19.5996(2) _cell_angle_alpha 96.1540(10) _cell_angle_beta 100.6200(10) _cell_angle_gamma 112.4000(10) _cell_volume 1606.71(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9866 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 30.02 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details 'program SADABS' _exptl_special_details ; Crystals from dichloromethane / diethyl ether by vapour diffusion. Bruker Kappa APEX-2 CCD diffractometer. ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 30738 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9308 _reflns_number_gt 8348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0439P)^2^+1.3211P] 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 9308 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.56611(2) 0.38722(2) 0.248413(10) 0.01575(5) Uani 1 1 d . . . S1 S 0.81367(4) 0.57870(4) 0.25959(2) 0.01784(8) Uani 1 1 d . . . S2 S 0.65708(5) 0.15801(4) 0.36258(2) 0.02064(8) Uani 1 1 d . . . P1 P 0.77179(4) 0.71332(4) 0.32752(2) 0.01371(8) Uani 1 1 d . . . P2 P 0.50409(5) 0.22250(4) 0.15037(2) 0.01448(8) Uani 1 1 d . . . F1 F 0.67730(19) 0.1095(2) 0.49169(8) 0.0604(5) Uani 1 1 d . . . F2 F 0.68470(18) 0.32487(16) 0.48111(7) 0.0467(3) Uani 1 1 d . . . F3 F 0.46163(15) 0.13149(18) 0.44457(7) 0.0464(3) Uani 1 1 d . . . O1 O 0.5815(2) 0.24306(18) 0.32768(8) 0.0381(4) Uani 1 1 d . . . O2 O 0.57426(18) -0.00089(15) 0.33677(9) 0.0365(3) Uani 1 1 d . . . O3 O 0.82848(18) 0.21759(17) 0.37547(10) 0.0396(4) Uani 1 1 d . . . N1 N 0.43300(16) 0.46178(15) 0.30020(7) 0.0166(2) Uani 1 1 d . . . N2 N 0.58843(16) 0.71449(15) 0.30411(8) 0.0172(2) Uani 1 1 d . . . H2n H 0.588(3) 0.794(3) 0.3093(12) 0.021 Uiso 1 1 d . . . C1 C 0.44887(18) 0.60351(17) 0.31208(8) 0.0160(3) Uani 1 1 d . . . C2 C 0.3313(2) 0.6433(2) 0.33251(9) 0.0218(3) Uani 1 1 d . . . H2 H 0.3426 0.7437 0.3379 0.026 Uiso 1 1 calc R . . C3 C 0.1990(2) 0.5330(2) 0.34454(10) 0.0259(4) Uani 1 1 d . . . H3 H 0.1163 0.5564 0.3573 0.031 Uiso 1 1 calc R . . C4 C 0.1866(2) 0.3873(2) 0.33792(9) 0.0247(3) Uani 1 1 d . . . H4 H 0.0993 0.3112 0.3488 0.030 Uiso 1 1 calc R . . C5 C 0.30442(19) 0.35644(19) 0.31522(9) 0.0208(3) Uani 1 1 d . . . H5 H 0.2954 0.2567 0.3098 0.025 Uiso 1 1 calc R . . C6 C 0.90181(19) 0.90790(17) 0.33189(8) 0.0179(3) Uani 1 1 d . . . H6 H 0.8744 0.9716 0.3658 0.022 Uiso 1 1 calc R . . C7 C 0.8734(2) 0.95027(19) 0.25914(10) 0.0242(3) Uani 1 1 d . . . H7A H 0.9454 1.0545 0.2622 0.036 Uiso 1 1 calc R . . H7B H 0.7618 0.9377 0.2441 0.036 Uiso 1 1 calc R . . H7C H 0.8950 0.8857 0.2246 0.036 Uiso 1 1 calc R . . C8 C 1.0785(2) 0.93702(19) 0.35928(10) 0.0235(3) Uani 1 1 d . . . H8A H 1.1052 0.8693 0.3289 0.035 Uiso 1 1 calc R . . H8B H 1.0965 0.9199 0.4079 0.035 Uiso 1 1 calc R . . H8C H 1.1466 1.0405 0.3586 0.035 Uiso 1 1 calc R . . C9 C 0.78305(19) 0.66545(18) 0.41557(8) 0.0187(3) Uani 1 1 d . . . H9 H 0.6813 0.5765 0.4117 0.022 Uiso 1 1 calc R . . C10 C 0.9197(2) 0.6187(2) 0.44101(10) 0.0249(3) Uani 1 1 d . . . H10A H 1.0224 0.7000 0.4424 0.037 Uiso 1 1 calc R . . H10B H 0.9054 0.5297 0.4084 0.037 Uiso 1 1 calc R . . H10C H 0.9187 0.5965 0.4885 0.037 Uiso 1 1 calc R . . C11 C 0.7837(3) 0.7896(2) 0.46961(10) 0.0299(4) Uani 1 1 d . . . H11A H 0.7659 0.7532 0.5132 0.045 Uiso 1 1 calc R . . H11B H 0.6980 0.8196 0.4501 0.045 Uiso 1 1 calc R . . H11C H 0.8875 0.8755 0.4801 0.045 Uiso 1 1 calc R . . C12 C 0.37658(18) 0.24135(18) 0.07277(8) 0.0176(3) Uani 1 1 d . . . C13 C 0.3929(2) 0.3846(2) 0.06600(10) 0.0249(3) Uani 1 1 d . . . H13 H 0.4628 0.4669 0.1027 0.030 Uiso 1 1 calc R . . C14 C 0.3073(2) 0.4081(2) 0.00565(12) 0.0333(4) Uani 1 1 d . . . H14 H 0.3200 0.5064 0.0013 0.040 Uiso 1 1 calc R . . C15 C 0.2044(2) 0.2896(3) -0.04768(11) 0.0333(4) Uani 1 1 d . . . H15 H 0.1472 0.3064 -0.0889 0.040 Uiso 1 1 calc R . . C16 C 0.1845(3) 0.1461(3) -0.04111(11) 0.0352(4) Uani 1 1 d . . . H16 H 0.1123 0.0641 -0.0776 0.042 Uiso 1 1 calc R . . C17 C 0.2703(2) 0.1219(2) 0.01898(10) 0.0278(4) Uani 1 1 d . . . H17 H 0.2563 0.0232 0.0233 0.033 Uiso 1 1 calc R . . C18 C 0.41369(19) 0.02431(17) 0.15307(8) 0.0177(3) Uani 1 1 d . . . C19 C 0.2731(2) -0.0306(2) 0.17680(9) 0.0251(3) Uani 1 1 d . . . H19 H 0.2255 0.0346 0.1900 0.030 Uiso 1 1 calc R . . C20 C 0.2026(2) -0.1803(2) 0.18115(10) 0.0298(4) Uani 1 1 d . . . H20 H 0.1057 -0.2173 0.1962 0.036 Uiso 1 1 calc R . . C21 C 0.2733(3) -0.2755(2) 0.16363(10) 0.0304(4) Uani 1 1 d . . . H21 H 0.2253 -0.3775 0.1670 0.037 Uiso 1 1 calc R . . C22 C 0.4141(2) -0.2217(2) 0.14121(10) 0.0278(4) Uani 1 1 d . . . H22 H 0.4635 -0.2865 0.1299 0.033 Uiso 1 1 calc R . . C23 C 0.4832(2) -0.07311(18) 0.13519(9) 0.0210(3) Uani 1 1 d . . . H23 H 0.5784 -0.0375 0.1188 0.025 Uiso 1 1 calc R . . C24 C 0.68671(18) 0.24488(16) 0.12217(8) 0.0158(3) Uani 1 1 d . . . C25 C 0.8222(2) 0.26442(19) 0.17420(8) 0.0198(3) Uani 1 1 d . . . H25 H 0.8165 0.2653 0.2221 0.024 Uiso 1 1 calc R . . C26 C 0.9650(2) 0.2825(2) 0.15576(10) 0.0254(3) Uani 1 1 d . . . H26 H 1.0559 0.2934 0.1910 0.031 Uiso 1 1 calc R . . C27 C 0.9750(2) 0.2846(2) 0.08605(10) 0.0273(4) Uani 1 1 d . . . H27 H 1.0729 0.2979 0.0737 0.033 Uiso 1 1 calc R . . C28 C 0.8421(2) 0.2674(2) 0.03452(9) 0.0242(3) Uani 1 1 d . . . H28 H 0.8497 0.2703 -0.0130 0.029 Uiso 1 1 calc R . . C29 C 0.6976(2) 0.24590(18) 0.05210(8) 0.0191(3) Uani 1 1 d . . . H29 H 0.6062 0.2319 0.0163 0.023 Uiso 1 1 calc R . . C30 C 0.6186(2) 0.1828(2) 0.44977(10) 0.0288(4) 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 Cu1 0.01656(9) 0.01398(9) 0.01727(9) 0.00187(7) 0.00624(7) 0.00623(7) S1 0.01582(16) 0.01515(17) 0.02291(18) 0.00086(13) 0.00900(13) 0.00555(13) S2 0.02522(19) 0.01613(18) 0.0260(2) 0.00620(14) 0.01134(15) 0.01140(15) P1 0.01360(16) 0.01299(17) 0.01618(17) 0.00327(13) 0.00521(13) 0.00640(13) P2 0.01620(17) 0.01316(17) 0.01497(17) 0.00227(13) 0.00491(13) 0.00660(13) F1 0.0489(8) 0.0702(11) 0.0462(8) 0.0415(8) -0.0057(7) 0.0075(8) F2 0.0494(8) 0.0451(8) 0.0316(6) -0.0081(6) 0.0150(6) 0.0061(6) F3 0.0279(6) 0.0634(9) 0.0427(7) 0.0111(7) 0.0203(5) 0.0076(6) O1 0.0634(10) 0.0380(8) 0.0285(7) 0.0186(6) 0.0137(7) 0.0330(8) O2 0.0305(7) 0.0190(6) 0.0583(10) -0.0034(6) 0.0089(7) 0.0120(5) O3 0.0269(7) 0.0278(7) 0.0657(11) 0.0028(7) 0.0260(7) 0.0078(6) N1 0.0155(6) 0.0161(6) 0.0191(6) 0.0036(5) 0.0067(5) 0.0064(5) N2 0.0156(6) 0.0143(6) 0.0256(7) 0.0060(5) 0.0067(5) 0.0091(5) C1 0.0142(6) 0.0177(7) 0.0167(6) 0.0025(5) 0.0039(5) 0.0075(5) C2 0.0189(7) 0.0254(8) 0.0249(8) 0.0026(6) 0.0064(6) 0.0135(6) C3 0.0168(7) 0.0360(10) 0.0263(8) 0.0010(7) 0.0079(6) 0.0125(7) C4 0.0161(7) 0.0305(9) 0.0239(8) 0.0037(7) 0.0084(6) 0.0046(6) C5 0.0174(7) 0.0196(7) 0.0227(7) 0.0035(6) 0.0071(6) 0.0040(6) C6 0.0182(7) 0.0136(7) 0.0219(7) 0.0034(5) 0.0056(5) 0.0061(5) C7 0.0249(8) 0.0191(8) 0.0279(8) 0.0104(6) 0.0069(6) 0.0068(6) C8 0.0170(7) 0.0202(8) 0.0276(8) 0.0046(6) 0.0029(6) 0.0029(6) C9 0.0193(7) 0.0200(7) 0.0179(7) 0.0043(6) 0.0055(5) 0.0087(6) C10 0.0221(8) 0.0268(9) 0.0270(8) 0.0096(7) 0.0029(6) 0.0115(7) C11 0.0429(11) 0.0306(9) 0.0214(8) 0.0028(7) 0.0119(7) 0.0193(8) C12 0.0161(6) 0.0205(7) 0.0187(7) 0.0054(5) 0.0059(5) 0.0091(6) C13 0.0200(7) 0.0203(8) 0.0333(9) 0.0101(7) 0.0040(6) 0.0070(6) C14 0.0262(9) 0.0345(10) 0.0443(11) 0.0234(9) 0.0087(8) 0.0136(8) C15 0.0291(9) 0.0515(13) 0.0278(9) 0.0198(9) 0.0076(7) 0.0223(9) C16 0.0366(10) 0.0425(12) 0.0227(9) 0.0008(8) -0.0032(7) 0.0185(9) C17 0.0332(9) 0.0264(9) 0.0229(8) 0.0010(7) -0.0006(7) 0.0156(7) C18 0.0218(7) 0.0140(7) 0.0154(7) 0.0026(5) 0.0035(5) 0.0060(6) C19 0.0265(8) 0.0217(8) 0.0242(8) 0.0036(6) 0.0097(6) 0.0056(6) C20 0.0305(9) 0.0242(9) 0.0239(8) 0.0057(7) 0.0076(7) -0.0011(7) C21 0.0418(10) 0.0152(8) 0.0214(8) 0.0055(6) -0.0014(7) 0.0015(7) C22 0.0375(10) 0.0162(8) 0.0252(8) 0.0026(6) -0.0010(7) 0.0106(7) C23 0.0251(8) 0.0167(7) 0.0208(7) 0.0028(6) 0.0030(6) 0.0095(6) C24 0.0189(7) 0.0129(6) 0.0173(7) 0.0025(5) 0.0064(5) 0.0077(5) C25 0.0228(7) 0.0212(7) 0.0169(7) 0.0030(6) 0.0054(6) 0.0105(6) C26 0.0204(8) 0.0321(9) 0.0238(8) 0.0028(7) 0.0035(6) 0.0124(7) C27 0.0211(8) 0.0349(10) 0.0289(9) 0.0069(7) 0.0109(7) 0.0124(7) C28 0.0263(8) 0.0313(9) 0.0201(7) 0.0079(6) 0.0109(6) 0.0142(7) C29 0.0217(7) 0.0208(7) 0.0169(7) 0.0039(5) 0.0057(6) 0.0105(6) C30 0.0233(8) 0.0353(10) 0.0239(8) 0.0130(7) 0.0074(7) 0.0051(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 N1 2.0261(13) . ? Cu1 P2 2.2099(4) . ? Cu1 O1 2.2395(14) . ? Cu1 S1 2.3101(4) . ? S1 P1 1.9756(5) . ? S2 O3 1.4338(15) . ? S2 O1 1.4376(14) . ? S2 O2 1.4430(14) . ? S2 C30 1.8197(19) . ? P1 N2 1.6870(14) . ? P1 C6 1.8237(16) . ? P1 C9 1.8330(16) . ? P2 C12 1.8216(16) . ? P2 C24 1.8233(15) . ? P2 C18 1.8261(16) . ? F1 C30 1.327(2) . ? F2 C30 1.322(2) . ? F3 C30 1.329(2) . ? N1 C1 1.342(2) . ? N1 C5 1.359(2) . ? N2 C1 1.393(2) . ? N2 H2n 0.78(2) . ? C1 C2 1.402(2) . ? C2 C3 1.378(2) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C8 1.533(2) . ? C6 C7 1.534(2) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.530(2) . ? C9 C11 1.531(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.390(2) . ? C12 C17 1.394(2) . ? C13 C14 1.393(3) . ? C13 H13 0.9500 . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.394(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.398(2) . ? C18 C19 1.399(2) . ? C19 C20 1.391(3) . ? C19 H19 0.9500 . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.396(2) . ? C24 C25 1.401(2) . ? C25 C26 1.392(2) . ? C25 H25 0.9500 . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.392(2) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? 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 Cu1 P2 132.86(4) . . ? N1 Cu1 O1 90.06(6) . . ? P2 Cu1 O1 99.03(4) . . ? N1 Cu1 S1 109.84(4) . . ? P2 Cu1 S1 109.710(16) . . ? O1 Cu1 S1 110.71(5) . . ? P1 S1 Cu1 92.247(18) . . ? O3 S2 O1 115.79(10) . . ? O3 S2 O2 115.63(9) . . ? O1 S2 O2 113.91(10) . . ? O3 S2 C30 104.73(9) . . ? O1 S2 C30 100.81(9) . . ? O2 S2 C30 103.34(10) . . ? N2 P1 C6 101.43(7) . . ? N2 P1 C9 104.19(7) . . ? C6 P1 C9 111.64(7) . . ? N2 P1 S1 114.56(5) . . ? C6 P1 S1 111.16(5) . . ? C9 P1 S1 113.13(6) . . ? C12 P2 C24 103.06(7) . . ? C12 P2 C18 104.27(7) . . ? C24 P2 C18 103.39(7) . . ? C12 P2 Cu1 116.54(5) . . ? C24 P2 Cu1 109.07(5) . . ? C18 P2 Cu1 118.69(5) . . ? S2 O1 Cu1 151.01(11) . . ? C1 N1 C5 117.63(13) . . ? C1 N1 Cu1 125.06(10) . . ? C5 N1 Cu1 116.67(11) . . ? C1 N2 P1 123.79(11) . . ? C1 N2 H2n 113.0(16) . . ? P1 N2 H2n 114.9(16) . . ? N1 C1 N2 118.21(13) . . ? N1 C1 C2 122.51(15) . . ? N2 C1 C2 119.29(14) . . ? C3 C2 C1 118.32(16) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.91(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.13(16) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.20(16) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C8 C6 C7 110.77(14) . . ? C8 C6 P1 110.74(11) . . ? C7 C6 P1 110.46(11) . . ? C8 C6 H6 108.3 . . ? C7 C6 H6 108.3 . . ? P1 C6 H6 108.3 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 112.27(15) . . ? C10 C9 P1 114.37(12) . . ? C11 C9 P1 110.96(12) . . ? C10 C9 H9 106.2 . . ? C11 C9 H9 106.2 . . ? P1 C9 H9 106.2 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.81(16) . . ? C13 C12 P2 117.34(13) . . ? C17 C12 P2 123.79(13) . . ? C12 C13 C14 120.35(17) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.44(18) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.90(18) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 119.98(19) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.51(18) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C23 C18 C19 118.84(15) . . ? C23 C18 P2 122.51(13) . . ? C19 C18 P2 118.60(13) . . ? C20 C19 C18 120.30(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.27(18) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.90(17) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.16(18) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.52(17) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? C29 C24 C25 119.24(14) . . ? C29 C24 P2 123.14(12) . . ? C25 C24 P2 117.61(11) . . ? C26 C25 C24 120.11(15) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C25 120.20(16) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C28 C27 C26 119.98(16) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.29(16) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C28 C29 C24 120.16(15) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? F2 C30 F1 107.63(17) . . ? F2 C30 F3 108.13(18) . . ? F1 C30 F3 107.92(16) . . ? F2 C30 S2 111.48(13) . . ? F1 C30 S2 111.22(16) . . ? F3 C30 S2 110.31(13) . . ? 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 N1 Cu1 S1 P1 7.20(5) . . . . ? P2 Cu1 S1 P1 161.022(19) . . . . ? O1 Cu1 S1 P1 -90.70(5) . . . . ? Cu1 S1 P1 N2 -45.31(6) . . . . ? Cu1 S1 P1 C6 -159.55(6) . . . . ? Cu1 S1 P1 C9 73.91(6) . . . . ? N1 Cu1 P2 C12 49.26(8) . . . . ? O1 Cu1 P2 C12 147.82(7) . . . . ? S1 Cu1 P2 C12 -96.25(6) . . . . ? N1 Cu1 P2 C24 165.36(7) . . . . ? O1 Cu1 P2 C24 -96.09(7) . . . . ? S1 Cu1 P2 C24 19.84(6) . . . . ? N1 Cu1 P2 C18 -76.71(8) . . . . ? O1 Cu1 P2 C18 21.84(8) . . . . ? S1 Cu1 P2 C18 137.77(6) . . . . ? O3 S2 O1 Cu1 36.3(3) . . . . ? O2 S2 O1 Cu1 -101.4(2) . . . . ? C30 S2 O1 Cu1 148.6(2) . . . . ? N1 Cu1 O1 S2 -159.9(2) . . . . ? P2 Cu1 O1 S2 66.5(2) . . . . ? S1 Cu1 O1 S2 -48.6(2) . . . . ? P2 Cu1 N1 C1 -118.58(12) . . . . ? O1 Cu1 N1 C1 139.01(13) . . . . ? S1 Cu1 N1 C1 26.90(14) . . . . ? P2 Cu1 N1 C5 51.99(14) . . . . ? O1 Cu1 N1 C5 -50.42(12) . . . . ? S1 Cu1 N1 C5 -162.53(11) . . . . ? C6 P1 N2 C1 -161.95(13) . . . . ? C9 P1 N2 C1 -45.89(15) . . . . ? S1 P1 N2 C1 78.23(13) . . . . ? C5 N1 C1 N2 173.30(14) . . . . ? Cu1 N1 C1 N2 -16.2(2) . . . . ? C5 N1 C1 C2 -6.2(2) . . . . ? Cu1 N1 C1 C2 164.25(12) . . . . ? P1 N2 C1 N1 -37.4(2) . . . . ? P1 N2 C1 C2 142.18(13) . . . . ? N1 C1 C2 C3 3.7(2) . . . . ? N2 C1 C2 C3 -175.85(15) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? C2 C3 C4 C5 -3.8(3) . . . . ? C1 N1 C5 C4 3.8(2) . . . . ? Cu1 N1 C5 C4 -167.49(13) . . . . ? C3 C4 C5 N1 1.1(3) . . . . ? N2 P1 C6 C8 174.86(11) . . . . ? C9 P1 C6 C8 64.41(13) . . . . ? S1 P1 C6 C8 -62.94(12) . . . . ? N2 P1 C6 C7 -62.05(13) . . . . ? C9 P1 C6 C7 -172.50(11) . . . . ? S1 P1 C6 C7 60.16(12) . . . . ? N2 P1 C9 C10 165.33(12) . . . . ? C6 P1 C9 C10 -85.99(13) . . . . ? S1 P1 C9 C10 40.29(13) . . . . ? N2 P1 C9 C11 -66.42(14) . . . . ? C6 P1 C9 C11 42.27(14) . . . . ? S1 P1 C9 C11 168.54(11) . . . . ? C24 P2 C12 C13 -86.81(14) . . . . ? C18 P2 C12 C13 165.48(13) . . . . ? Cu1 P2 C12 C13 32.58(15) . . . . ? C24 P2 C12 C17 90.15(16) . . . . ? C18 P2 C12 C17 -17.56(16) . . . . ? Cu1 P2 C12 C17 -150.46(13) . . . . ? C17 C12 C13 C14 -1.5(3) . . . . ? P2 C12 C13 C14 175.56(14) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? C13 C12 C17 C16 1.3(3) . . . . ? P2 C12 C17 C16 -175.66(15) . . . . ? C12 P2 C18 C23 106.83(14) . . . . ? C24 P2 C18 C23 -0.64(15) . . . . ? Cu1 P2 C18 C23 -121.51(13) . . . . ? C12 P2 C18 C19 -75.92(14) . . . . ? C24 P2 C18 C19 176.61(13) . . . . ? Cu1 P2 C18 C19 55.74(15) . . . . ? C23 C18 C19 C20 -1.2(3) . . . . ? P2 C18 C19 C20 -178.53(14) . . . . ? C18 C19 C20 C21 1.6(3) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C20 C21 C22 C23 -1.0(3) . . . . ? C21 C22 C23 C18 1.4(3) . . . . ? C19 C18 C23 C22 -0.3(2) . . . . ? P2 C18 C23 C22 176.96(13) . . . . ? C12 P2 C24 C29 -10.68(15) . . . . ? C18 P2 C24 C29 97.70(14) . . . . ? Cu1 P2 C24 C29 -135.12(12) . . . . ? C12 P2 C24 C25 168.20(12) . . . . ? C18 P2 C24 C25 -83.42(13) . . . . ? Cu1 P2 C24 C25 43.76(13) . . . . ? C29 C24 C25 C26 -0.9(2) . . . . ? P2 C24 C25 C26 -179.80(13) . . . . ? C24 C25 C26 C27 1.4(3) . . . . ? C25 C26 C27 C28 -0.6(3) . . . . ? C26 C27 C28 C29 -0.9(3) . . . . ? C27 C28 C29 C24 1.4(3) . . . . ? C25 C24 C29 C28 -0.6(2) . . . . ? P2 C24 C29 C28 178.31(13) . . . . ? O3 S2 C30 F2 59.63(17) . . . . ? O1 S2 C30 F2 -60.91(16) . . . . ? O2 S2 C30 F2 -178.91(14) . . . . ? O3 S2 C30 F1 -60.50(16) . . . . ? O1 S2 C30 F1 178.96(14) . . . . ? O2 S2 C30 F1 60.96(15) . . . . ? O3 S2 C30 F3 179.78(14) . . . . ? O1 S2 C30 F3 59.24(17) . . . . ? O2 S2 C30 F3 -58.76(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2n O2 0.78(2) 2.10(2) 2.8775(19) 172(2) 1_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.270 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.073 #===END