# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ? _publ_contact_author_email c.e.willans@leeds.ac.uk _publ_contact_author_phone ? _publ_contact_author_name 'Charlotte Willans' loop_ _publ_author_name C.Willans B.Lake E.Bullough T.Williams 'Adrian Whitwood' M.Little data_brml41 _database_code_depnum_ccdc_archive 'CCDC 865136' #TrackingRef 'web_deposit_cif_file_0_CharlotteWillans_1327938890.BRML41.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H40 Cu N4, F6 P' _chemical_formula_sum 'C38 H40 Cu F6 N4 P' _chemical_formula_weight 761.25 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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 14.0778(4) _cell_length_b 15.5817(5) _cell_length_c 17.3053(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.4220(10) _cell_angle_gamma 90.00 _cell_volume 3707.16(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8169 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 28.246 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6609 _exptl_absorpt_correction_T_max 0.8678 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_device_type 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 58537 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.31 _reflns_number_total 9198 _reflns_number_gt 7395 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3, 0.98\A, aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq of the parent atom. 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^)+(0.0497P)^2^+1.9360P] 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 9198 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.467493(16) 0.756149(12) 0.230175(13) 0.02132(7) Uani 1 1 d . . . P1 P 0.58625(4) 0.27412(3) 0.27458(3) 0.02590(11) Uani 1 1 d . . . C9 C 0.48110(12) 0.87695(11) 0.23424(10) 0.0209(3) Uani 1 1 d . . . N4 N 0.50871(11) 0.92606(9) 0.30010(9) 0.0230(3) Uani 1 1 d . . . N3 N 0.47032(11) 0.93366(9) 0.17376(9) 0.0217(3) Uani 1 1 d . . . C10 C 0.49078(15) 1.01657(12) 0.20118(12) 0.0287(4) Uani 1 1 d . . . H10 H 0.4883 1.0670 0.1700 0.034 Uiso 1 1 calc R . . C11 C 0.51486(14) 1.01181(12) 0.28052(12) 0.0287(4) Uani 1 1 d . . . H11 H 0.5327 1.0582 0.3163 0.034 Uiso 1 1 calc R . . C6 C 0.51267(15) 0.87784(13) 0.05416(12) 0.0302(4) Uani 1 1 d . . . F4 F 0.68108(12) 0.22830(11) 0.25884(10) 0.0605(4) Uani 1 1 d . . . F3 F 0.58605(11) 0.33416(9) 0.19965(8) 0.0497(4) Uani 1 1 d . . . C18 C 0.45777(15) 0.90209(13) 0.42447(12) 0.0308(4) Uani 1 1 d . . . F1 F 0.58522(14) 0.21238(11) 0.34767(10) 0.0644(5) Uani 1 1 d . . . F2 F 0.48951(11) 0.31832(9) 0.28881(10) 0.0576(4) Uani 1 1 d . . . F5 F 0.52232(13) 0.20538(11) 0.21774(10) 0.0671(5) Uani 1 1 d . . . C5 C 0.44158(14) 0.90885(11) 0.09181(10) 0.0231(3) Uani 1 1 d . . . F6 F 0.64845(14) 0.34236(13) 0.33003(10) 0.0768(6) Uani 1 1 d . . . C12 C 0.52783(14) 0.89091(11) 0.37900(11) 0.0253(4) Uani 1 1 d . . . C3 C 0.34407(15) 0.91633(13) 0.05410(12) 0.0312(4) Uani 1 1 d . . . N2 N 0.40239(11) 0.59189(9) 0.27629(9) 0.0255(3) Uani 1 1 d . . . N1 N 0.48254(11) 0.57409(9) 0.18563(10) 0.0249(3) Uani 1 1 d . . . C28 C 0.45212(13) 0.63583(11) 0.23024(10) 0.0221(3) Uani 1 1 d . . . C31 C 0.54228(14) 0.58974(11) 0.12908(11) 0.0251(4) Uani 1 1 d . . . C24 C 0.36196(14) 0.63046(11) 0.33772(11) 0.0257(4) Uani 1 1 d . . . C25 C 0.41703(15) 0.62679(13) 0.41500(13) 0.0329(4) Uani 1 1 d . . . C22 C 0.27075(15) 0.66928(12) 0.31794(12) 0.0305(4) Uani 1 1 d . . . C13 C 0.61426(15) 0.84558(14) 0.40538(12) 0.0335(4) Uani 1 1 d . . . C23 C 0.21446(17) 0.67413(16) 0.23372(14) 0.0429(5) Uani 1 1 d . . . H23A H 0.1469 0.6898 0.2330 0.064 Uiso 1 1 calc R . . H23B H 0.2161 0.6182 0.2082 0.064 Uiso 1 1 calc R . . H23C H 0.2437 0.7175 0.2051 0.064 Uiso 1 1 calc R . . C17 C 0.47705(18) 0.86542(15) 0.49978(13) 0.0393(5) Uani 1 1 d . . . H17 H 0.4311 0.8718 0.5324 0.047 Uiso 1 1 calc R . . C8 C 0.48222(17) 0.85290(14) -0.02494(12) 0.0361(5) Uani 1 1 d . . . H8 H 0.5286 0.8308 -0.0523 0.043 Uiso 1 1 calc R . . C1 C 0.38628(18) 0.85969(14) -0.06387(12) 0.0384(5) Uani 1 1 d . . . H1 H 0.3671 0.8425 -0.1176 0.046 Uiso 1 1 calc R . . C26 C 0.51839(18) 0.58941(18) 0.43301(15) 0.0491(6) Uani 1 1 d . . . H26A H 0.5447 0.5910 0.4902 0.074 Uiso 1 1 calc R . . H26B H 0.5603 0.6231 0.4060 0.074 Uiso 1 1 calc R . . H26C H 0.5160 0.5299 0.4145 0.074 Uiso 1 1 calc R . . C32 C 0.49720(17) 0.61388(13) 0.05257(13) 0.0352(5) Uani 1 1 d . . . C16 C 0.56110(18) 0.82031(16) 0.52764(13) 0.0446(6) Uani 1 1 d . . . H16 H 0.5727 0.7959 0.5791 0.054 Uiso 1 1 calc R . . C37 C 0.64263(15) 0.57878(12) 0.15354(13) 0.0321(4) Uani 1 1 d . . . C27 C 0.37658(18) 0.66118(15) 0.47482(14) 0.0416(5) Uani 1 1 d . . . H27 H 0.4116 0.6583 0.5282 0.050 Uiso 1 1 calc R . . C29 C 0.40225(16) 0.50457(12) 0.26088(14) 0.0354(5) Uani 1 1 d . . . H29 H 0.3724 0.4610 0.2858 0.043 Uiso 1 1 calc R . . C30 C 0.45236(16) 0.49363(12) 0.20405(14) 0.0351(5) Uani 1 1 d . . . H30 H 0.4648 0.4407 0.1808 0.042 Uiso 1 1 calc R . . C20 C 0.28602(19) 0.69946(15) 0.45727(15) 0.0441(6) Uani 1 1 d . . . H20 H 0.2593 0.7229 0.4986 0.053 Uiso 1 1 calc R . . C21 C 0.23400(17) 0.70394(14) 0.37999(15) 0.0401(5) Uani 1 1 d . . . H21 H 0.1721 0.7311 0.3688 0.048 Uiso 1 1 calc R . . C2 C 0.31785(17) 0.89144(15) -0.02483(13) 0.0393(5) Uani 1 1 d . . . H2 H 0.2520 0.8963 -0.0523 0.047 Uiso 1 1 calc R . . C36 C 0.69856(18) 0.59205(15) 0.09714(16) 0.0468(6) Uani 1 1 d . . . H36 H 0.7671 0.5850 0.1115 0.056 Uiso 1 1 calc R . . C15 C 0.62946(17) 0.80996(16) 0.48120(13) 0.0416(5) Uani 1 1 d . . . H15 H 0.6872 0.7783 0.5012 0.050 Uiso 1 1 calc R . . C34 C 0.5566(2) 0.62694(15) -0.00160(14) 0.0474(6) Uani 1 1 d . . . H34 H 0.5283 0.6440 -0.0542 0.057 Uiso 1 1 calc R . . C7 C 0.61754(17) 0.87025(19) 0.09636(15) 0.0500(6) Uani 1 1 d . . . H7A H 0.6275 0.8158 0.1253 0.075 Uiso 1 1 calc R . . H7B H 0.6344 0.9180 0.1337 0.075 Uiso 1 1 calc R . . H7C H 0.6591 0.8720 0.0576 0.075 Uiso 1 1 calc R . . C14 C 0.68761(17) 0.83357(19) 0.35421(15) 0.0482(6) Uani 1 1 d . . . H14A H 0.7444 0.8027 0.3842 0.072 Uiso 1 1 calc R . . H14B H 0.7080 0.8898 0.3382 0.072 Uiso 1 1 calc R . . H14C H 0.6581 0.8004 0.3070 0.072 Uiso 1 1 calc R . . C19 C 0.36367(17) 0.94804(16) 0.39323(15) 0.0440(5) Uani 1 1 d . . . H19A H 0.3772 1.0050 0.3741 0.066 Uiso 1 1 calc R . . H19B H 0.3278 0.9541 0.4356 0.066 Uiso 1 1 calc R . . H19C H 0.3245 0.9150 0.3496 0.066 Uiso 1 1 calc R . . C38 C 0.68891(17) 0.55401(17) 0.23746(15) 0.0463(6) Uani 1 1 d . . . H38A H 0.7598 0.5527 0.2439 0.070 Uiso 1 1 calc R . . H38B H 0.6657 0.4971 0.2490 0.070 Uiso 1 1 calc R . . H38C H 0.6713 0.5962 0.2740 0.070 Uiso 1 1 calc R . . C4 C 0.26899(17) 0.94876(19) 0.09769(15) 0.0500(6) Uani 1 1 d . . . H4A H 0.2058 0.9534 0.0607 0.075 Uiso 1 1 calc R . . H4B H 0.2887 1.0053 0.1204 0.075 Uiso 1 1 calc R . . H4C H 0.2638 0.9086 0.1402 0.075 Uiso 1 1 calc R . . C33 C 0.38945(19) 0.62653(18) 0.02824(16) 0.0534(6) Uani 1 1 d . . . H33A H 0.3719 0.6818 0.0484 0.080 Uiso 1 1 calc R . . H33B H 0.3562 0.5801 0.0501 0.080 Uiso 1 1 calc R . . H33C H 0.3697 0.6260 -0.0296 0.080 Uiso 1 1 calc R . . C35 C 0.6554(2) 0.61537(16) 0.02068(17) 0.0533(7) Uani 1 1 d . . . H35 H 0.6946 0.6235 -0.0170 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 0.02857(12) 0.01756(11) 0.01848(12) -0.00027(8) 0.00652(9) -0.00061(8) P1 0.0327(3) 0.0243(2) 0.0220(3) -0.00078(18) 0.0089(2) -0.00183(18) C9 0.0237(8) 0.0214(8) 0.0182(8) -0.0013(6) 0.0060(7) -0.0017(6) N4 0.0294(8) 0.0218(7) 0.0178(8) -0.0014(6) 0.0055(6) -0.0037(6) N3 0.0283(8) 0.0189(7) 0.0180(7) 0.0003(5) 0.0054(6) -0.0006(5) C10 0.0402(11) 0.0201(8) 0.0266(10) 0.0004(7) 0.0090(8) -0.0045(7) C11 0.0381(10) 0.0204(8) 0.0286(10) -0.0040(7) 0.0093(8) -0.0070(7) C6 0.0352(10) 0.0344(10) 0.0238(10) 0.0044(8) 0.0123(8) 0.0038(8) F4 0.0553(9) 0.0765(11) 0.0563(10) 0.0236(8) 0.0265(8) 0.0319(8) F3 0.0653(9) 0.0476(8) 0.0419(8) 0.0184(6) 0.0243(7) 0.0155(7) C18 0.0365(10) 0.0321(9) 0.0254(10) -0.0038(8) 0.0100(8) -0.0063(8) F1 0.0983(13) 0.0575(9) 0.0477(9) 0.0251(7) 0.0389(9) 0.0173(9) F2 0.0565(9) 0.0430(8) 0.0863(12) 0.0120(7) 0.0443(9) 0.0126(6) F5 0.0824(12) 0.0565(9) 0.0637(11) -0.0278(8) 0.0186(9) -0.0280(9) C5 0.0327(9) 0.0201(8) 0.0168(8) 0.0015(6) 0.0061(7) 0.0009(7) F6 0.0880(13) 0.0902(13) 0.0523(10) -0.0316(9) 0.0155(9) -0.0482(11) C12 0.0322(9) 0.0254(8) 0.0177(9) -0.0015(7) 0.0039(7) -0.0062(7) C3 0.0328(10) 0.0340(10) 0.0265(10) -0.0033(8) 0.0057(8) 0.0024(8) N2 0.0295(8) 0.0209(7) 0.0281(9) 0.0011(6) 0.0107(7) 0.0012(6) N1 0.0280(8) 0.0197(7) 0.0284(9) -0.0007(6) 0.0094(7) 0.0014(6) C28 0.0244(8) 0.0207(8) 0.0214(9) 0.0007(6) 0.0057(7) 0.0018(6) C31 0.0332(9) 0.0201(8) 0.0246(10) -0.0032(7) 0.0117(8) -0.0008(7) C24 0.0303(9) 0.0230(8) 0.0269(10) -0.0002(7) 0.0129(8) -0.0046(7) C25 0.0350(11) 0.0347(10) 0.0294(11) 0.0045(8) 0.0076(8) -0.0052(8) C22 0.0315(10) 0.0294(9) 0.0326(11) -0.0011(8) 0.0111(8) -0.0011(8) C13 0.0327(10) 0.0399(11) 0.0248(10) -0.0024(8) -0.0008(8) -0.0043(8) C23 0.0339(11) 0.0534(14) 0.0388(13) -0.0010(10) 0.0024(9) 0.0078(10) C17 0.0509(13) 0.0462(12) 0.0235(11) -0.0028(9) 0.0140(10) -0.0131(10) C8 0.0481(13) 0.0412(11) 0.0228(10) 0.0005(8) 0.0163(9) 0.0061(9) C1 0.0553(14) 0.0409(11) 0.0191(10) -0.0030(8) 0.0081(9) -0.0030(10) C26 0.0416(13) 0.0620(16) 0.0406(14) 0.0112(12) 0.0022(11) 0.0053(11) C32 0.0473(12) 0.0302(10) 0.0283(11) -0.0017(8) 0.0086(9) 0.0025(9) C16 0.0550(15) 0.0547(14) 0.0202(11) 0.0050(9) -0.0007(10) -0.0141(11) C37 0.0319(10) 0.0281(9) 0.0380(12) -0.0031(8) 0.0113(9) -0.0019(8) C27 0.0528(14) 0.0470(13) 0.0269(11) -0.0013(9) 0.0126(10) -0.0111(10) C29 0.0450(12) 0.0203(8) 0.0468(13) 0.0007(8) 0.0230(10) -0.0022(8) C30 0.0466(12) 0.0184(8) 0.0453(13) -0.0015(8) 0.0213(10) -0.0001(8) C20 0.0560(14) 0.0453(12) 0.0392(14) -0.0097(10) 0.0285(11) -0.0093(11) C21 0.0370(11) 0.0399(11) 0.0493(14) -0.0058(10) 0.0222(10) 0.0007(9) C2 0.0379(12) 0.0491(13) 0.0271(11) -0.0045(9) -0.0015(9) 0.0000(10) C36 0.0397(12) 0.0441(12) 0.0638(17) -0.0031(12) 0.0274(12) -0.0017(10) C15 0.0398(12) 0.0493(13) 0.0291(12) 0.0056(10) -0.0074(9) -0.0027(10) C34 0.0817(19) 0.0373(12) 0.0279(12) 0.0004(9) 0.0221(12) 0.0009(12) C7 0.0342(12) 0.0816(18) 0.0365(13) -0.0005(12) 0.0126(10) 0.0129(12) C14 0.0334(12) 0.0721(17) 0.0380(13) 0.0019(12) 0.0051(10) 0.0102(11) C19 0.0428(12) 0.0498(13) 0.0445(14) 0.0048(11) 0.0206(11) 0.0050(10) C38 0.0337(12) 0.0533(14) 0.0484(15) 0.0051(11) 0.0008(10) -0.0002(10) C4 0.0328(11) 0.0732(17) 0.0430(14) -0.0157(12) 0.0057(10) 0.0124(11) C33 0.0518(15) 0.0585(16) 0.0418(14) 0.0071(12) -0.0076(12) 0.0085(12) C35 0.0753(19) 0.0438(13) 0.0556(17) -0.0039(11) 0.0469(15) -0.0047(12) _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 C28 1.8873(17) . ? Cu1 C9 1.8918(17) . ? P1 F6 1.5673(16) . ? P1 F4 1.5882(15) . ? P1 F1 1.5917(14) . ? P1 F2 1.5918(14) . ? P1 F5 1.5950(15) . ? P1 F3 1.5985(13) . ? C9 N3 1.353(2) . ? C9 N4 1.358(2) . ? N4 C11 1.386(2) . ? N4 C12 1.442(2) . ? N3 C10 1.385(2) . ? N3 C5 1.441(2) . ? C10 C11 1.344(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C6 C5 1.393(3) . ? C6 C8 1.399(3) . ? C6 C7 1.504(3) . ? C18 C17 1.395(3) . ? C18 C12 1.399(3) . ? C18 C19 1.501(3) . ? C5 C3 1.392(3) . ? C12 C13 1.396(3) . ? C3 C2 1.391(3) . ? C3 C4 1.511(3) . ? N2 C28 1.354(2) . ? N2 C29 1.386(2) . ? N2 C24 1.441(2) . ? N1 C28 1.359(2) . ? N1 C30 1.383(2) . ? N1 C31 1.442(2) . ? C31 C32 1.391(3) . ? C31 C37 1.395(3) . ? C24 C22 1.394(3) . ? C24 C25 1.395(3) . ? C25 C27 1.392(3) . ? C25 C26 1.510(3) . ? C22 C21 1.397(3) . ? C22 C23 1.504(3) . ? C13 C15 1.398(3) . ? C13 C14 1.510(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C17 C16 1.371(4) . ? C17 H17 0.9500 . ? C8 C1 1.378(3) . ? C8 H8 0.9500 . ? C1 C2 1.382(3) . ? C1 H1 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C32 C34 1.399(3) . ? C32 C33 1.497(3) . ? C16 C15 1.390(3) . ? C16 H16 0.9500 . ? C37 C36 1.395(3) . ? C37 C38 1.508(3) . ? C27 C20 1.381(4) . ? C27 H27 0.9500 . ? C29 C30 1.339(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C20 C21 1.381(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C2 H2 0.9500 . ? C36 C35 1.380(4) . ? C36 H36 0.9500 . ? C15 H15 0.9500 . ? C34 C35 1.374(4) . ? C34 H34 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C35 H35 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 C28 Cu1 C9 177.55(7) . . ? F6 P1 F4 91.74(11) . . ? F6 P1 F1 91.31(10) . . ? F4 P1 F1 90.93(9) . . ? F6 P1 F2 89.75(10) . . ? F4 P1 F2 178.50(10) . . ? F1 P1 F2 89.09(9) . . ? F6 P1 F5 179.46(12) . . ? F4 P1 F5 88.63(10) . . ? F1 P1 F5 89.07(10) . . ? F2 P1 F5 89.87(10) . . ? F6 P1 F3 90.17(10) . . ? F4 P1 F3 88.79(8) . . ? F1 P1 F3 178.50(10) . . ? F2 P1 F3 91.15(8) . . ? F5 P1 F3 89.45(9) . . ? N3 C9 N4 104.21(14) . . ? N3 C9 Cu1 128.85(13) . . ? N4 C9 Cu1 126.88(13) . . ? C9 N4 C11 111.07(15) . . ? C9 N4 C12 122.83(14) . . ? C11 N4 C12 126.10(15) . . ? C9 N3 C10 111.33(15) . . ? C9 N3 C5 123.16(14) . . ? C10 N3 C5 125.51(15) . . ? C11 C10 N3 106.66(16) . . ? C11 C10 H10 126.7 . . ? N3 C10 H10 126.7 . . ? C10 C11 N4 106.74(16) . . ? C10 C11 H11 126.6 . . ? N4 C11 H11 126.6 . . ? C5 C6 C8 117.03(19) . . ? C5 C6 C7 121.94(19) . . ? C8 C6 C7 121.02(19) . . ? C17 C18 C12 117.1(2) . . ? C17 C18 C19 120.75(19) . . ? C12 C18 C19 122.10(19) . . ? C3 C5 C6 123.02(18) . . ? C3 C5 N3 118.59(16) . . ? C6 C5 N3 118.39(17) . . ? C13 C12 C18 123.33(18) . . ? C13 C12 N4 118.30(17) . . ? C18 C12 N4 118.35(17) . . ? C2 C3 C5 117.61(18) . . ? C2 C3 C4 121.1(2) . . ? C5 C3 C4 121.26(18) . . ? C28 N2 C29 111.25(15) . . ? C28 N2 C24 124.03(15) . . ? C29 N2 C24 124.53(15) . . ? C28 N1 C30 111.15(15) . . ? C28 N1 C31 124.54(14) . . ? C30 N1 C31 124.25(15) . . ? N2 C28 N1 104.03(14) . . ? N2 C28 Cu1 125.20(13) . . ? N1 C28 Cu1 130.74(13) . . ? C32 C31 C37 123.14(18) . . ? C32 C31 N1 118.58(17) . . ? C37 C31 N1 118.28(17) . . ? C22 C24 C25 123.08(18) . . ? C22 C24 N2 119.29(18) . . ? C25 C24 N2 117.63(17) . . ? C27 C25 C24 117.7(2) . . ? C27 C25 C26 121.0(2) . . ? C24 C25 C26 121.28(19) . . ? C24 C22 C21 116.9(2) . . ? C24 C22 C23 121.69(18) . . ? C21 C22 C23 121.4(2) . . ? C12 C13 C15 117.0(2) . . ? C12 C13 C14 121.93(19) . . ? C15 C13 C14 121.0(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 . . ? C16 C17 C18 121.2(2) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C1 C8 C6 121.28(19) . . ? C1 C8 H8 119.4 . . ? C6 C8 H8 119.4 . . ? C8 C1 C2 120.1(2) . . ? C8 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C31 C32 C34 117.5(2) . . ? C31 C32 C33 122.0(2) . . ? C34 C32 C33 120.5(2) . . ? C17 C16 C15 120.6(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C36 C37 C31 117.2(2) . . ? C36 C37 C38 121.3(2) . . ? C31 C37 C38 121.52(18) . . ? C20 C27 C25 120.6(2) . . ? C20 C27 H27 119.7 . . ? C25 C27 H27 119.7 . . ? C30 C29 N2 106.68(17) . . ? C30 C29 H29 126.7 . . ? N2 C29 H29 126.7 . . ? C29 C30 N1 106.88(16) . . ? C29 C30 H30 126.6 . . ? N1 C30 H30 126.6 . . ? C27 C20 C21 120.5(2) . . ? C27 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 121.2(2) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C1 C2 C3 120.9(2) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C35 C36 C37 120.8(2) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C16 C15 C13 120.8(2) . . ? C16 C15 H15 119.6 . . ? C13 C15 H15 119.6 . . ? C35 C34 C32 120.5(2) . . ? C35 C34 H34 119.7 . . ? C32 C34 H34 119.7 . . ? 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 . . ? 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 . . ? 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 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C34 C35 C36 120.9(2) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? 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 N3 C9 N4 C11 0.0(2) . . . . ? Cu1 C9 N4 C11 177.38(13) . . . . ? N3 C9 N4 C12 179.67(15) . . . . ? Cu1 C9 N4 C12 -3.0(2) . . . . ? N4 C9 N3 C10 0.0(2) . . . . ? Cu1 C9 N3 C10 -177.29(14) . . . . ? N4 C9 N3 C5 179.72(15) . . . . ? Cu1 C9 N3 C5 2.4(3) . . . . ? C9 N3 C10 C11 0.0(2) . . . . ? C5 N3 C10 C11 -179.72(17) . . . . ? N3 C10 C11 N4 0.0(2) . . . . ? C9 N4 C11 C10 0.0(2) . . . . ? C12 N4 C11 C10 -179.67(17) . . . . ? C8 C6 C5 C3 -0.6(3) . . . . ? C7 C6 C5 C3 -179.9(2) . . . . ? C8 C6 C5 N3 178.91(16) . . . . ? C7 C6 C5 N3 -0.4(3) . . . . ? C9 N3 C5 C3 97.1(2) . . . . ? C10 N3 C5 C3 -83.2(2) . . . . ? C9 N3 C5 C6 -82.4(2) . . . . ? C10 N3 C5 C6 97.2(2) . . . . ? C17 C18 C12 C13 0.0(3) . . . . ? C19 C18 C12 C13 -177.4(2) . . . . ? C17 C18 C12 N4 178.33(17) . . . . ? C19 C18 C12 N4 0.9(3) . . . . ? C9 N4 C12 C13 74.7(2) . . . . ? C11 N4 C12 C13 -105.7(2) . . . . ? C9 N4 C12 C18 -103.7(2) . . . . ? C11 N4 C12 C18 75.9(2) . . . . ? C6 C5 C3 C2 0.0(3) . . . . ? N3 C5 C3 C2 -179.54(18) . . . . ? C6 C5 C3 C4 178.8(2) . . . . ? N3 C5 C3 C4 -0.7(3) . . . . ? C29 N2 C28 N1 0.3(2) . . . . ? C24 N2 C28 N1 175.52(17) . . . . ? C29 N2 C28 Cu1 178.34(15) . . . . ? C24 N2 C28 Cu1 -6.4(3) . . . . ? C30 N1 C28 N2 -0.2(2) . . . . ? C31 N1 C28 N2 -177.50(17) . . . . ? C30 N1 C28 Cu1 -178.12(16) . . . . ? C31 N1 C28 Cu1 4.6(3) . . . . ? C28 N1 C31 C32 -85.5(2) . . . . ? C30 N1 C31 C32 97.6(2) . . . . ? C28 N1 C31 C37 95.4(2) . . . . ? C30 N1 C31 C37 -81.6(2) . . . . ? C28 N2 C24 C22 84.3(2) . . . . ? C29 N2 C24 C22 -101.1(2) . . . . ? C28 N2 C24 C25 -95.8(2) . . . . ? C29 N2 C24 C25 78.8(2) . . . . ? C22 C24 C25 C27 2.3(3) . . . . ? N2 C24 C25 C27 -177.67(17) . . . . ? C22 C24 C25 C26 -175.8(2) . . . . ? N2 C24 C25 C26 4.3(3) . . . . ? C25 C24 C22 C21 -1.4(3) . . . . ? N2 C24 C22 C21 178.58(17) . . . . ? C25 C24 C22 C23 178.37(19) . . . . ? N2 C24 C22 C23 -1.7(3) . . . . ? C18 C12 C13 C15 0.3(3) . . . . ? N4 C12 C13 C15 -178.07(18) . . . . ? C18 C12 C13 C14 179.0(2) . . . . ? N4 C12 C13 C14 0.7(3) . . . . ? C12 C18 C17 C16 -0.1(3) . . . . ? C19 C18 C17 C16 177.3(2) . . . . ? C5 C6 C8 C1 0.7(3) . . . . ? C7 C6 C8 C1 180.0(2) . . . . ? C6 C8 C1 C2 -0.1(3) . . . . ? C37 C31 C32 C34 0.4(3) . . . . ? N1 C31 C32 C34 -178.70(17) . . . . ? C37 C31 C32 C33 -179.0(2) . . . . ? N1 C31 C32 C33 1.9(3) . . . . ? C18 C17 C16 C15 0.0(4) . . . . ? C32 C31 C37 C36 -0.8(3) . . . . ? N1 C31 C37 C36 178.31(18) . . . . ? C32 C31 C37 C38 178.9(2) . . . . ? N1 C31 C37 C38 -2.0(3) . . . . ? C24 C25 C27 C20 -1.7(3) . . . . ? C26 C25 C27 C20 176.4(2) . . . . ? C28 N2 C29 C30 -0.2(3) . . . . ? C24 N2 C29 C30 -175.47(19) . . . . ? N2 C29 C30 N1 0.1(3) . . . . ? C28 N1 C30 C29 0.0(3) . . . . ? C31 N1 C30 C29 177.37(19) . . . . ? C25 C27 C20 C21 0.2(3) . . . . ? C27 C20 C21 C22 0.7(3) . . . . ? C24 C22 C21 C20 -0.2(3) . . . . ? C23 C22 C21 C20 -179.9(2) . . . . ? C8 C1 C2 C3 -0.5(4) . . . . ? C5 C3 C2 C1 0.6(3) . . . . ? C4 C3 C2 C1 -178.3(2) . . . . ? C31 C37 C36 C35 0.2(3) . . . . ? C38 C37 C36 C35 -179.5(2) . . . . ? C17 C16 C15 C13 0.3(4) . . . . ? C12 C13 C15 C16 -0.4(3) . . . . ? C14 C13 C15 C16 -179.2(2) . . . . ? C31 C32 C34 C35 0.6(3) . . . . ? C33 C32 C34 C35 180.0(2) . . . . ? C32 C34 C35 C36 -1.1(4) . . . . ? C37 C36 C35 C34 0.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.508 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.062 # Attachment 'web_deposit_cif_file_1_CharlotteWillans_1327938890.ijsf1115.cif' data_ijsf1115 _database_code_depnum_ccdc_archive 'CCDC 865137' #TrackingRef 'web_deposit_cif_file_1_CharlotteWillans_1327938890.ijsf1115.cif' _audit_creation_date 2011-09-13 _audit_creation_method ; Olex2 1.1 (compiled 2011.09.07 svn.r1971, GUI svn.r3853) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H36 Br2 Cu2 N4' _chemical_formula_sum 'C42 H36 Br2 Cu2 N4' _chemical_formula_weight 883.65 _chemical_melting_point ? _chemical_oxdiff_formula 'C21 H18 Br1 Cu1 N2' _chemical_oxdiff_usercomment "Tom's BRML58" 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4581(6) _cell_length_b 9.5482(7) _cell_length_c 11.2949(10) _cell_angle_alpha 69.206(7) _cell_angle_beta 82.837(6) _cell_angle_gamma 69.262(6) _cell_volume 891.80(12) _cell_formula_units_Z 1 _cell_measurement_reflns_used 3571 _cell_measurement_temperature 110.00(10) _cell_measurement_theta_max 31.2520 _cell_measurement_theta_min 2.9964 _exptl_absorpt_coefficient_mu 3.470 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_correction_T_min 0.579 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'dull ? colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 444 _exptl_crystal_size_max 0.217 _exptl_crystal_size_mid 0.1108 _exptl_crystal_size_min 0.0626 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8485 _diffrn_reflns_theta_full 29.07 _diffrn_reflns_theta_max 31.32 _diffrn_reflns_theta_min 3.00 _diffrn_ambient_temperature 110.00(10) _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.9956 _diffrn_measured_fraction_theta_max 0.887 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -35.00 9.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -23.1156 -84.0000 -133.0000 44 #__ type_ start__ end____ width___ exp.time_ 2 omega -20.00 67.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 24.6781 -99.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 3 omega 60.00 101.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 24.6781 -178.0000 -180.0000 41 #__ type_ start__ end____ width___ exp.time_ 4 omega 4.00 89.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 24.6781 57.0000 -150.0000 85 #__ type_ start__ end____ width___ exp.time_ 5 omega -46.00 97.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 24.6781 0.0000 0.0000 143 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0773826000 _diffrn_orient_matrix_UB_12 -0.0281660000 _diffrn_orient_matrix_UB_13 0.0168238000 _diffrn_orient_matrix_UB_21 0.0207234000 _diffrn_orient_matrix_UB_22 -0.0171925000 _diffrn_orient_matrix_UB_23 -0.0571610000 _diffrn_orient_matrix_UB_31 0.0035803000 _diffrn_orient_matrix_UB_32 0.0775774000 _diffrn_orient_matrix_UB_33 -0.0310147000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4252 _reflns_number_total 5176 _reflns_odcompleteness_completeness 99.56 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 29.07 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.177 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 5176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0406 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.6919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.0953 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.88769(3) 0.86509(3) 0.01639(3) 0.02247(8) Uani 1 1 d . . . C1 C 0.6870(3) 1.2503(3) 0.1094(3) 0.0140(5) Uani 1 1 d . . . C2 C 0.4412(3) 1.3572(3) 0.1612(2) 0.0133(5) Uani 1 1 d . . . C3 C 0.2877(3) 1.3886(3) 0.1890(3) 0.0161(5) Uani 1 1 d . . . H3 H 0.2377 1.3207 0.1884 0.019 Uiso 1 1 calc R . . C4 C 0.2135(3) 1.5265(3) 0.2176(3) 0.0192(5) Uani 1 1 d . . . H4 H 0.1109 1.5521 0.2365 0.023 Uiso 1 1 calc R . . C5 C 0.2898(3) 1.6282(3) 0.2186(3) 0.0197(5) Uani 1 1 d . . . H5 H 0.2360 1.7201 0.2376 0.024 Uiso 1 1 calc R . . C6 C 0.4429(3) 1.5958(3) 0.1921(3) 0.0169(5) Uani 1 1 d . . . H6 H 0.4934 1.6628 0.1936 0.020 Uiso 1 1 calc R . . C7 C 0.5172(3) 1.4573(3) 0.1629(2) 0.0134(5) Uani 1 1 d . . . C8 C 0.5152(3) 1.0960(3) 0.1240(3) 0.0158(5) Uani 1 1 d . . . H8A H 0.5947 1.0403 0.0775 0.019 Uiso 1 1 calc R . . H8B H 0.4207 1.1325 0.0793 0.019 Uiso 1 1 calc R . . C9 C 0.5040(3) 0.9826(3) 0.2558(2) 0.0133(5) Uani 1 1 d . . . C10 C 0.6192(3) 0.9276(3) 0.3441(3) 0.0197(5) Uani 1 1 d . . . H10 H 0.7031 0.9608 0.3221 0.024 Uiso 1 1 calc R . . C12 C 0.4855(4) 0.7714(3) 0.4976(3) 0.0233(6) Uani 1 1 d . . . H12 H 0.4800 0.6999 0.5779 0.028 Uiso 1 1 calc R . . C13 C 0.6086(3) 0.8234(3) 0.4646(3) 0.0227(6) Uani 1 1 d . . . H13 H 0.6848 0.7884 0.5235 0.027 Uiso 1 1 calc R . . C14 C 0.3712(3) 0.8257(3) 0.4114(3) 0.0240(6) Uani 1 1 d . . . H14 H 0.2883 0.7909 0.4335 0.029 Uiso 1 1 calc R . . C15 C 0.3794(3) 0.9328(3) 0.2908(3) 0.0188(5) Uani 1 1 d . . . H15 H 0.3007 0.9710 0.2336 0.023 Uiso 1 1 calc R . . C16 C 0.7913(3) 1.4465(3) 0.1303(3) 0.0160(5) Uani 1 1 d . . . H16A H 0.7545 1.5617 0.0968 0.019 Uiso 1 1 calc R . . H16B H 0.8706 1.4086 0.0746 0.019 Uiso 1 1 calc R . . C17 C 0.8564(3) 1.3922(3) 0.2618(3) 0.0159(5) Uani 1 1 d . . . C18 C 0.9635(3) 1.2420(3) 0.3103(3) 0.0196(5) Uani 1 1 d . . . H18 H 0.9950 1.1750 0.2622 0.023 Uiso 1 1 calc R . . C19 C 1.0236(3) 1.1918(3) 0.4304(3) 0.0217(6) Uani 1 1 d . . . H19 H 1.0965 1.0919 0.4617 0.026 Uiso 1 1 calc R . . C20 C 0.9757(3) 1.2895(4) 0.5039(3) 0.0218(6) Uani 1 1 d . . . H20 H 1.0151 1.2552 0.5846 0.026 Uiso 1 1 calc R . . C21 C 0.8684(3) 1.4388(3) 0.4559(3) 0.0212(6) Uani 1 1 d . . . H21 H 0.8357 1.5048 0.5048 0.025 Uiso 1 1 calc R . . C22 C 0.8094(3) 1.4905(3) 0.3354(3) 0.0186(5) Uani 1 1 d . . . H22 H 0.7381 1.5913 0.3037 0.022 Uiso 1 1 calc R . . Cu1 Cu 0.86386(4) 1.11836(4) 0.04996(3) 0.01957(9) Uani 1 1 d . . . N1 N 0.5474(2) 1.2331(2) 0.1279(2) 0.0135(4) Uani 1 1 d . . . N2 N 0.6671(2) 1.3875(2) 0.1316(2) 0.0132(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 Br1 0.01446(13) 0.02129(14) 0.03516(18) -0.01419(12) 0.00375(11) -0.00652(10) C1 0.0136(11) 0.0148(11) 0.0148(12) -0.0048(10) 0.0003(9) -0.0063(9) C2 0.0139(11) 0.0149(11) 0.0097(11) -0.0018(9) -0.0004(9) -0.0055(9) C3 0.0137(12) 0.0193(12) 0.0145(13) -0.0033(10) 0.0021(9) -0.0076(10) C4 0.0142(12) 0.0237(13) 0.0161(13) -0.0051(11) 0.0019(10) -0.0042(10) C5 0.0214(13) 0.0180(12) 0.0161(14) -0.0053(10) 0.0012(11) -0.0031(11) C6 0.0206(13) 0.0152(12) 0.0148(13) -0.0044(10) 0.0010(10) -0.0071(10) C7 0.0125(11) 0.0151(11) 0.0113(12) -0.0024(9) 0.0004(9) -0.0049(9) C8 0.0163(12) 0.0184(12) 0.0156(13) -0.0066(10) -0.0001(10) -0.0081(10) C9 0.0142(11) 0.0113(11) 0.0154(13) -0.0060(9) 0.0013(9) -0.0044(9) C10 0.0164(12) 0.0191(12) 0.0226(15) -0.0038(11) -0.0025(11) -0.0071(10) C12 0.0341(16) 0.0171(13) 0.0174(14) -0.0020(11) 0.0034(12) -0.0119(12) C13 0.0237(14) 0.0200(13) 0.0205(15) -0.0023(11) -0.0051(11) -0.0053(11) C14 0.0249(14) 0.0263(14) 0.0255(16) -0.0069(12) 0.0064(12) -0.0179(12) C15 0.0176(12) 0.0191(13) 0.0216(14) -0.0054(11) -0.0002(10) -0.0098(11) C16 0.0151(12) 0.0187(12) 0.0164(13) -0.0048(10) 0.0021(10) -0.0099(10) C17 0.0150(12) 0.0180(12) 0.0179(13) -0.0058(10) 0.0018(10) -0.0101(10) C18 0.0156(12) 0.0197(13) 0.0259(15) -0.0096(11) 0.0023(11) -0.0076(10) C19 0.0159(12) 0.0201(13) 0.0274(16) -0.0048(11) -0.0029(11) -0.0063(11) C20 0.0195(13) 0.0304(15) 0.0187(14) -0.0049(12) -0.0009(11) -0.0152(12) C21 0.0208(13) 0.0271(14) 0.0224(15) -0.0120(12) 0.0015(11) -0.0125(12) C22 0.0171(12) 0.0190(12) 0.0228(14) -0.0073(11) 0.0001(10) -0.0096(10) Cu1 0.01534(16) 0.02226(18) 0.02025(19) -0.00870(14) 0.00149(13) -0.00418(13) N1 0.0152(10) 0.0129(9) 0.0131(11) -0.0026(8) 0.0008(8) -0.0076(8) N2 0.0131(10) 0.0134(10) 0.0135(11) -0.0032(8) 0.0009(8) -0.0064(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 Br1 Cu1 2.5073(5) . ? Br1 Cu1 2.4183(5) 2_775 ? C1 Cu1 1.914(3) . ? C1 N1 1.369(3) . ? C1 N2 1.365(3) . ? C2 C3 1.393(3) . ? C2 C7 1.390(3) . ? C2 N1 1.391(3) . ? C3 H3 0.9300 . ? C3 C4 1.385(4) . ? C4 H4 0.9300 . ? C4 C5 1.404(4) . ? C5 H5 0.9300 . ? C5 C6 1.387(4) . ? C6 H6 0.9300 . ? C6 C7 1.394(4) . ? C7 N2 1.398(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.516(4) . ? C8 N1 1.461(3) . ? C9 C10 1.396(4) . ? C9 C15 1.386(4) . ? C10 H10 0.9300 . ? C10 C13 1.389(4) . ? C12 H12 0.9300 . ? C12 C13 1.382(4) . ? C12 C14 1.376(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C14 C15 1.396(4) . ? C15 H15 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.520(4) . ? C16 N2 1.467(3) . ? C17 C18 1.392(4) . ? C17 C22 1.391(4) . ? C18 H18 0.9300 . ? C18 C19 1.389(4) . ? C19 H19 0.9300 . ? C19 C20 1.386(4) . ? C20 H20 0.9300 . ? C20 C21 1.385(4) . ? C21 H21 0.9300 . ? C21 C22 1.387(4) . ? C22 H22 0.9300 . ? Cu1 Br1 2.4183(5) 2_775 ? 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 Cu1 Br1 Cu1 79.757(15) 2_775 . ? N1 C1 Cu1 126.29(18) . . ? N2 C1 Cu1 128.60(19) . . ? N2 C1 N1 104.9(2) . . ? C7 C2 C3 122.2(2) . . ? C7 C2 N1 106.4(2) . . ? N1 C2 C3 131.4(2) . . ? C2 C3 H3 121.8 . . ? C4 C3 C2 116.4(2) . . ? C4 C3 H3 121.8 . . ? C3 C4 H4 119.3 . . ? C3 C4 C5 121.5(3) . . ? C5 C4 H4 119.3 . . ? C4 C5 H5 119.0 . . ? C6 C5 C4 121.9(3) . . ? C6 C5 H5 119.0 . . ? C5 C6 H6 121.8 . . ? C5 C6 C7 116.5(2) . . ? C7 C6 H6 121.8 . . ? C2 C7 C6 121.5(2) . . ? C2 C7 N2 105.9(2) . . ? C6 C7 N2 132.6(2) . . ? H8A C8 H8B 107.9 . . ? C9 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? N1 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? N1 C8 C9 111.7(2) . . ? C10 C9 C8 120.3(2) . . ? C15 C9 C8 120.6(2) . . ? C15 C9 C10 119.0(2) . . ? C9 C10 H10 120.0 . . ? C13 C10 C9 120.1(3) . . ? C13 C10 H10 120.0 . . ? C13 C12 H12 120.1 . . ? C14 C12 H12 120.1 . . ? C14 C12 C13 119.8(3) . . ? C10 C13 H13 119.8 . . ? C12 C13 C10 120.5(3) . . ? C12 C13 H13 119.8 . . ? C12 C14 H14 119.9 . . ? C12 C14 C15 120.2(3) . . ? C15 C14 H14 119.9 . . ? C9 C15 C14 120.4(3) . . ? C9 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? H16A C16 H16B 107.9 . . ? C17 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? N2 C16 H16A 109.2 . . ? N2 C16 H16B 109.2 . . ? N2 C16 C17 111.9(2) . . ? C18 C17 C16 119.9(2) . . ? C22 C17 C16 120.9(2) . . ? C22 C17 C18 119.2(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C18 C19 H19 119.8 . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C19 C20 H20 120.3 . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C20 C21 H21 119.8 . . ? C20 C21 C22 120.5(3) . . ? C22 C21 H21 119.8 . . ? C17 C22 H22 119.8 . . ? C21 C22 C17 120.3(3) . . ? C21 C22 H22 119.8 . . ? Br1 Cu1 Br1 100.242(15) 2_775 . ? C1 Cu1 Br1 134.16(8) . 2_775 ? C1 Cu1 Br1 125.58(8) . . ? C1 N1 C2 111.3(2) . . ? C1 N1 C8 124.8(2) . . ? C2 N1 C8 123.7(2) . . ? C1 N2 C7 111.4(2) . . ? C1 N2 C16 123.3(2) . . ? C7 N2 C16 125.1(2) . . ? 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 C2 C3 C4 C5 -0.2(4) . . . . ? C2 C7 N2 C1 0.7(3) . . . . ? C2 C7 N2 C16 -175.6(2) . . . . ? C3 C2 C7 C6 -0.3(4) . . . . ? C3 C2 C7 N2 179.5(2) . . . . ? C3 C2 N1 C1 -179.8(3) . . . . ? C3 C2 N1 C8 -4.6(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C5 C6 C7 N2 179.9(3) . . . . ? C6 C7 N2 C1 -179.5(3) . . . . ? C6 C7 N2 C16 4.3(4) . . . . ? C7 C2 C3 C4 0.6(4) . . . . ? C7 C2 N1 C1 0.4(3) . . . . ? C7 C2 N1 C8 175.6(2) . . . . ? C8 C9 C10 C13 -179.8(3) . . . . ? C8 C9 C15 C14 178.6(3) . . . . ? C9 C8 N1 C1 100.5(3) . . . . ? C9 C8 N1 C2 -74.1(3) . . . . ? C9 C10 C13 C12 1.0(4) . . . . ? C10 C9 C15 C14 -1.8(4) . . . . ? C12 C14 C15 C9 1.5(4) . . . . ? C13 C12 C14 C15 0.1(5) . . . . ? C14 C12 C13 C10 -1.3(5) . . . . ? C15 C9 C10 C13 0.6(4) . . . . ? C16 C17 C18 C19 179.9(2) . . . . ? C16 C17 C22 C21 179.2(2) . . . . ? C17 C16 N2 C1 -93.7(3) . . . . ? C17 C16 N2 C7 82.2(3) . . . . ? C17 C18 C19 C20 1.1(4) . . . . ? C18 C17 C22 C21 -0.3(4) . . . . ? C18 C19 C20 C21 -0.8(4) . . . . ? C19 C20 C21 C22 -0.1(4) . . . . ? C20 C21 C22 C17 0.6(4) . . . . ? C22 C17 C18 C19 -0.6(4) . . . . ? Cu1 Br1 Cu1 Br1 -0.001(1) 2_775 . . 2_775 ? Cu1 Br1 Cu1 C1 178.90(10) 2_775 . . . ? Cu1 C1 N1 C2 -174.84(18) . . . . ? Cu1 C1 N1 C8 10.0(4) . . . . ? Cu1 C1 N2 C7 174.26(19) . . . . ? Cu1 C1 N2 C16 -9.4(4) . . . . ? N1 C1 Cu1 Br1 170.94(17) . . . 2_775 ? N1 C1 Cu1 Br1 -7.6(3) . . . . ? N1 C1 N2 C7 -0.4(3) . . . . ? N1 C1 N2 C16 175.9(2) . . . . ? N1 C2 C3 C4 -179.2(3) . . . . ? N1 C2 C7 C6 179.5(2) . . . . ? N1 C2 C7 N2 -0.6(3) . . . . ? N1 C8 C9 C10 -51.6(3) . . . . ? N1 C8 C9 C15 128.0(3) . . . . ? N2 C1 Cu1 Br1 178.86(19) . . . . ? N2 C1 Cu1 Br1 -2.6(3) . . . 2_775 ? N2 C1 N1 C2 0.0(3) . . . . ? N2 C1 N1 C8 -175.2(2) . . . . ? N2 C16 C17 C18 82.8(3) . . . . ? N2 C16 C17 C22 -96.6(3) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 1 0.0378 0.0000 0.0000 1.0000 0.0168 -0.0572 -0.0310 0 0 -1 0.0378 -0.0000 -0.0000 -1.0000 -0.0168 0.0572 0.0310 1 1 1 0.0955 1.0000 1.0000 1.0000 0.0660 -0.0536 0.0501 -1 -1 -1 0.0955 -1.0000 -1.0000 -1.0000 -0.0660 0.0536 -0.0501 0 -1 0 0.0535 -0.0000 -1.0000 -0.0000 0.0282 0.0172 -0.0776 0 1 0 0.0535 0.0000 1.0000 0.0000 -0.0282 -0.0172 0.0776 -2 -1 1 0.0942 -2.0000 -1.0000 1.0000 -0.1098 -0.0814 -0.1158 2 1 -1 0.0942 2.0000 1.0000 -1.0000 0.1098 0.0814 0.1158 0 -1 -2 0.0313 -0.0000 -1.0000 -2.0000 -0.0055 0.1315 -0.0155 0 1 2 0.0313 0.0000 1.0000 2.0000 0.0055 -0.1315 0.0155 1 -1 0 0.0582 1.0000 -1.0000 -0.0000 0.1055 0.0379 -0.0740 -2 2 -1 0.0452 -2.0000 2.0000 -1.0000 -0.2279 -0.0187 0.1790 # Attachment 'web_deposit_cif_file_2_CharlotteWillans_1327938890.BRML101.CIF' data_brml101 _database_code_depnum_ccdc_archive 'CCDC 865138' #TrackingRef 'web_deposit_cif_file_2_CharlotteWillans_1327938890.BRML101.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H36 Cu N4, F6 P' _chemical_formula_sum 'C42 H36 Cu F6 N4 P' _chemical_formula_weight 805.27 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0929(10) _cell_length_b 10.7824(15) _cell_length_c 11.7655(16) _cell_angle_alpha 69.473(5) _cell_angle_beta 86.792(4) _cell_angle_gamma 69.242(4) _cell_volume 896.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8105 _cell_measurement_theta_min 2.2945 _cell_measurement_theta_max 26.507 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 414 _exptl_absorpt_coefficient_mu 0.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8808 _exptl_absorpt_correction_T_max 0.9444 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_device_type 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12286 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.51 _reflns_number_total 3698 _reflns_number_gt 3356 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SUPERFLIP (Palatinus L., Chapuis G. (2007): Superflip - a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions. J. Appl. Cryst. 40, 786-790) ; _computing_structure_refinement ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH2 0.99\A, aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. 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^)+(0.0401P)^2^+0.4188P] 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 3698 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.0000 0.0000 1.0000 0.02438(9) Uani 1 2 d S . . C1 C 0.17073(18) 0.09009(15) 0.97092(14) 0.0218(3) Uani 1 1 d . . . N2 N 0.23646(16) 0.14281(13) 0.86392(11) 0.0208(3) Uani 1 1 d . . . C3 C 0.36651(18) 0.19296(15) 0.87966(14) 0.0216(3) Uani 1 1 d . . . C2 C 0.38071(19) 0.17031(16) 1.00344(14) 0.0227(3) Uani 1 1 d . . . N1 N 0.25896(16) 0.10642(13) 1.05573(11) 0.0218(3) Uani 1 1 d . . . C15 C 0.2204(2) 0.07085(17) 1.18357(14) 0.0273(3) Uani 1 1 d . . . H15A H 0.3199 0.0668 1.2317 0.033 Uiso 1 1 calc R . . H15B H 0.2117 -0.0245 1.2137 0.033 Uiso 1 1 calc R . . C16 C 0.05064(19) 0.17609(16) 1.20390(13) 0.0226(3) Uani 1 1 d . . . C17 C -0.0249(2) 0.31436(17) 1.12208(14) 0.0267(3) Uani 1 1 d . . . H17 H 0.0321 0.3463 1.0507 0.032 Uiso 1 1 calc R . . C18 C -0.1825(2) 0.40550(18) 1.14418(16) 0.0315(4) Uani 1 1 d . . . H18 H -0.2336 0.4997 1.0878 0.038 Uiso 1 1 calc R . . C19 C -0.2658(2) 0.35998(19) 1.24803(17) 0.0345(4) Uani 1 1 d . . . H19 H -0.3750 0.4223 1.2624 0.041 Uiso 1 1 calc R . . C20 C -0.1901(2) 0.2237(2) 1.33084(16) 0.0343(4) Uani 1 1 d . . . H20 H -0.2462 0.1927 1.4029 0.041 Uiso 1 1 calc R . . C21 C -0.0328(2) 0.13257(18) 1.30888(15) 0.0284(3) Uani 1 1 d . . . H21 H 0.0189 0.0391 1.3663 0.034 Uiso 1 1 calc R . . C4 C 0.5000(2) 0.20822(17) 1.05233(16) 0.0295(3) Uani 1 1 d . . . H4 H 0.5091 0.1937 1.1365 0.035 Uiso 1 1 calc R . . C6 C 0.6046(2) 0.26821(18) 0.97125(18) 0.0348(4) Uani 1 1 d . . . H6 H 0.6880 0.2956 1.0008 0.042 Uiso 1 1 calc R . . C7 C 0.5920(2) 0.28991(18) 0.84764(18) 0.0340(4) Uani 1 1 d . . . H7 H 0.6678 0.3305 0.7957 0.041 Uiso 1 1 calc R . . C5 C 0.4718(2) 0.25397(16) 0.79833(15) 0.0274(3) Uani 1 1 d . . . H5 H 0.4619 0.2700 0.7139 0.033 Uiso 1 1 calc R . . C8 C 0.1665(2) 0.15842(17) 0.74594(14) 0.0254(3) Uani 1 1 d . . . H8A H 0.1267 0.0785 0.7563 0.030 Uiso 1 1 calc R . . H8B H 0.2627 0.1531 0.6900 0.030 Uiso 1 1 calc R . . C9 C 0.01320(19) 0.29657(16) 0.68901(13) 0.0233(3) Uani 1 1 d . . . C10 C -0.0272(2) 0.40950(18) 0.72928(16) 0.0312(4) Uani 1 1 d . . . H10 H 0.0416 0.4007 0.7964 0.037 Uiso 1 1 calc R . . C11 C -0.1671(2) 0.53541(19) 0.67268(18) 0.0372(4) Uani 1 1 d . . . H11 H -0.1928 0.6123 0.7008 0.045 Uiso 1 1 calc R . . C12 C -0.2682(3) 0.54886(19) 0.57620(17) 0.0399(4) Uani 1 1 d . . . H12 H -0.3650 0.6344 0.5380 0.048 Uiso 1 1 calc R . . C13 C -0.2284(3) 0.4376(2) 0.53544(18) 0.0518(6) Uani 1 1 d . . . H13 H -0.2979 0.4468 0.4685 0.062 Uiso 1 1 calc R . . C14 C -0.0880(3) 0.3121(2) 0.59086(16) 0.0401(4) Uani 1 1 d . . . H14 H -0.0612 0.2364 0.5611 0.048 Uiso 1 1 calc R . . P1 P 0.5000 0.0000 0.5000 0.02339(13) Uani 1 2 d S . . F3 F 0.29341(13) 0.06735(12) 0.51219(10) 0.0417(3) Uani 1 1 d . . . F2 F 0.46224(14) -0.10213(10) 0.44084(9) 0.0341(2) Uani 1 1 d . . . F1 F 0.47830(15) 0.11759(11) 0.36742(8) 0.0395(3) 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 0.02124(14) 0.02572(15) 0.02771(16) -0.00848(11) 0.00326(10) -0.01134(11) C1 0.0183(7) 0.0207(7) 0.0246(7) -0.0084(6) 0.0018(5) -0.0045(6) N2 0.0191(6) 0.0222(6) 0.0221(6) -0.0090(5) 0.0015(5) -0.0074(5) C3 0.0165(6) 0.0201(7) 0.0272(8) -0.0093(6) 0.0017(6) -0.0042(6) C2 0.0170(7) 0.0214(7) 0.0277(8) -0.0091(6) 0.0005(6) -0.0039(6) N1 0.0180(6) 0.0248(6) 0.0211(6) -0.0081(5) 0.0017(5) -0.0061(5) C15 0.0256(8) 0.0296(8) 0.0202(8) -0.0061(6) 0.0011(6) -0.0048(7) C16 0.0225(7) 0.0265(8) 0.0224(7) -0.0112(6) 0.0000(6) -0.0100(6) C17 0.0264(8) 0.0279(8) 0.0264(8) -0.0090(7) 0.0024(6) -0.0109(6) C18 0.0314(8) 0.0253(8) 0.0365(9) -0.0124(7) -0.0014(7) -0.0065(7) C19 0.0277(8) 0.0377(10) 0.0442(10) -0.0255(8) 0.0078(7) -0.0087(7) C20 0.0367(9) 0.0427(10) 0.0336(9) -0.0212(8) 0.0146(7) -0.0200(8) C21 0.0339(8) 0.0277(8) 0.0256(8) -0.0103(7) 0.0044(6) -0.0129(7) C4 0.0221(7) 0.0286(8) 0.0376(9) -0.0148(7) -0.0050(6) -0.0049(6) C6 0.0201(7) 0.0312(9) 0.0564(12) -0.0186(8) -0.0025(7) -0.0090(7) C7 0.0213(8) 0.0262(8) 0.0524(11) -0.0110(8) 0.0090(7) -0.0097(6) C5 0.0230(7) 0.0235(8) 0.0319(9) -0.0081(7) 0.0065(6) -0.0064(6) C8 0.0265(7) 0.0277(8) 0.0233(8) -0.0122(6) 0.0005(6) -0.0080(6) C9 0.0223(7) 0.0263(8) 0.0209(7) -0.0071(6) 0.0043(6) -0.0097(6) C10 0.0266(8) 0.0300(9) 0.0399(9) -0.0154(7) -0.0015(7) -0.0101(7) C11 0.0345(9) 0.0267(9) 0.0501(11) -0.0143(8) 0.0021(8) -0.0097(7) C12 0.0398(10) 0.0291(9) 0.0332(9) -0.0012(7) -0.0029(8) -0.0008(8) C13 0.0574(13) 0.0494(12) 0.0322(10) -0.0142(9) -0.0196(9) 0.0031(10) C14 0.0465(11) 0.0373(10) 0.0312(9) -0.0179(8) -0.0089(8) -0.0014(8) P1 0.0265(3) 0.0249(3) 0.0173(3) -0.0083(2) 0.0001(2) -0.0065(2) F3 0.0274(5) 0.0515(7) 0.0471(6) -0.0264(5) 0.0037(4) -0.0064(5) F2 0.0446(6) 0.0327(5) 0.0284(5) -0.0146(4) -0.0027(4) -0.0132(4) F1 0.0572(7) 0.0400(6) 0.0204(5) -0.0025(4) -0.0042(4) -0.0235(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 C1 1.9066(15) . ? Cu1 C1 1.9066(15) 2_557 ? C1 N1 1.3523(19) . ? C1 N2 1.3522(19) . ? N2 C3 1.3891(19) . ? N2 C8 1.4604(19) . ? C3 C5 1.393(2) . ? C3 C2 1.394(2) . ? C2 N1 1.3928(19) . ? C2 C4 1.392(2) . ? N1 C15 1.4611(19) . ? C15 C16 1.510(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.388(2) . ? C16 C17 1.392(2) . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.382(3) . ? C18 H18 0.9500 . ? C19 C20 1.381(3) . ? C19 H19 0.9500 . ? C20 C21 1.381(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C4 C6 1.382(3) . ? C4 H4 0.9500 . ? C6 C7 1.393(3) . ? C6 H6 0.9500 . ? C7 C5 1.385(2) . ? C7 H7 0.9500 . ? C5 H5 0.9500 . ? C8 C9 1.513(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.380(2) . ? C9 C10 1.385(2) . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 C13 1.373(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? P1 F3 1.5902(10) . ? P1 F3 1.5902(10) 2_656 ? P1 F1 1.5992(9) 2_656 ? P1 F1 1.5992(9) . ? P1 F2 1.6095(9) 2_656 ? P1 F2 1.6095(9) . ? 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 C1 Cu1 C1 180.00(7) . 2_557 ? N1 C1 N2 105.82(12) . . ? N1 C1 Cu1 126.41(11) . . ? N2 C1 Cu1 127.65(11) . . ? C1 N2 C3 111.15(12) . . ? C1 N2 C8 124.10(12) . . ? C3 N2 C8 124.46(12) . . ? N2 C3 C5 132.14(14) . . ? N2 C3 C2 106.10(12) . . ? C5 C3 C2 121.76(14) . . ? N1 C2 C4 132.39(15) . . ? N1 C2 C3 105.76(13) . . ? C4 C2 C3 121.85(14) . . ? C1 N1 C2 111.17(12) . . ? C1 N1 C15 123.65(13) . . ? C2 N1 C15 125.02(13) . . ? N1 C15 C16 112.98(12) . . ? N1 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? N1 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C21 C16 C17 118.87(14) . . ? C21 C16 C15 118.35(14) . . ? C17 C16 C15 122.77(14) . . ? C18 C17 C16 120.32(15) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 120.20(16) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.86(16) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 120.01(16) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 120.72(16) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C6 C4 C2 116.11(16) . . ? C6 C4 H4 121.9 . . ? C2 C4 H4 121.9 . . ? C4 C6 C7 122.23(15) . . ? C4 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C5 C7 C6 121.85(15) . . ? C5 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C5 C3 116.19(15) . . ? C7 C5 H5 121.9 . . ? C3 C5 H5 121.9 . . ? N2 C8 C9 112.99(12) . . ? N2 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 118.57(15) . . ? C14 C9 C8 118.63(14) . . ? C10 C9 C8 122.77(14) . . ? C9 C10 C11 120.79(16) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.09(17) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.42(17) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 120.77(18) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 120.34(17) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? F3 P1 F3 180.00(8) . 2_656 ? F3 P1 F1 90.12(6) . 2_656 ? F3 P1 F1 89.88(6) 2_656 2_656 ? F3 P1 F1 89.88(6) . . ? F3 P1 F1 90.12(6) 2_656 . ? F1 P1 F1 180.00(5) 2_656 . ? F3 P1 F2 90.34(5) . 2_656 ? F3 P1 F2 89.66(5) 2_656 2_656 ? F1 P1 F2 89.98(5) 2_656 2_656 ? F1 P1 F2 90.02(5) . 2_656 ? F3 P1 F2 89.66(5) . . ? F3 P1 F2 90.34(5) 2_656 . ? F1 P1 F2 90.02(5) 2_656 . ? F1 P1 F2 89.98(5) . . ? F2 P1 F2 180.0 2_656 . ? 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 C1 N2 C3 -0.02(16) . . . . ? Cu1 C1 N2 C3 -176.39(10) . . . . ? N1 C1 N2 C8 -174.02(12) . . . . ? Cu1 C1 N2 C8 9.6(2) . . . . ? C1 N2 C3 C5 179.15(15) . . . . ? C8 N2 C3 C5 -6.9(2) . . . . ? C1 N2 C3 C2 -0.31(16) . . . . ? C8 N2 C3 C2 173.67(13) . . . . ? N2 C3 C2 N1 0.49(15) . . . . ? C5 C3 C2 N1 -179.03(13) . . . . ? N2 C3 C2 C4 179.94(14) . . . . ? C5 C3 C2 C4 0.4(2) . . . . ? N2 C1 N1 C2 0.34(16) . . . . ? Cu1 C1 N1 C2 176.78(10) . . . . ? N2 C1 N1 C15 176.07(13) . . . . ? Cu1 C1 N1 C15 -7.5(2) . . . . ? C4 C2 N1 C1 -179.89(16) . . . . ? C3 C2 N1 C1 -0.53(16) . . . . ? C4 C2 N1 C15 4.4(3) . . . . ? C3 C2 N1 C15 -176.19(13) . . . . ? C1 N1 C15 C16 -73.75(19) . . . . ? C2 N1 C15 C16 101.39(16) . . . . ? N1 C15 C16 C21 158.10(14) . . . . ? N1 C15 C16 C17 -22.0(2) . . . . ? C21 C16 C17 C18 -1.4(2) . . . . ? C15 C16 C17 C18 178.75(15) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C17 C18 C19 C20 1.0(3) . . . . ? C18 C19 C20 C21 -1.0(3) . . . . ? C19 C20 C21 C16 -0.2(3) . . . . ? C17 C16 C21 C20 1.3(2) . . . . ? C15 C16 C21 C20 -178.78(15) . . . . ? N1 C2 C4 C6 178.65(15) . . . . ? C3 C2 C4 C6 -0.6(2) . . . . ? C2 C4 C6 C7 0.1(2) . . . . ? C4 C6 C7 C5 0.7(3) . . . . ? C6 C7 C5 C3 -0.9(2) . . . . ? N2 C3 C5 C7 -179.00(15) . . . . ? C2 C3 C5 C7 0.4(2) . . . . ? C1 N2 C8 C9 85.94(17) . . . . ? C3 N2 C8 C9 -87.27(17) . . . . ? N2 C8 C9 C14 -166.84(15) . . . . ? N2 C8 C9 C10 14.8(2) . . . . ? C14 C9 C10 C11 0.4(3) . . . . ? C8 C9 C10 C11 178.71(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C10 C9 C14 C13 -0.9(3) . . . . ? C8 C9 C14 C13 -179.35(19) . . . . ? C12 C13 C14 C9 0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.302 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.044 # Attachment 'web_deposit_cif_file_3_CharlotteWillans_1327938890.BRML82.CIF' data_e:\phdx-r~1\brml82\work\comple~1\brml82 _database_code_depnum_ccdc_archive 'CCDC 865139' #TrackingRef 'web_deposit_cif_file_3_CharlotteWillans_1327938890.BRML82.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 Br2 Cu2 N4' _chemical_formula_sum 'C22 H24 Br2 Cu2 N4' _chemical_formula_weight 631.35 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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.8647(9) _cell_length_b 7.3597(7) _cell_length_c 16.2732(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.924(4) _cell_angle_gamma 90.00 _cell_volume 1175.15(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8089 _cell_measurement_theta_min 2.5165 _cell_measurement_theta_max 30.331 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624.33 _exptl_absorpt_coefficient_mu 5.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_T_max 0.876 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_device_type 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20429 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.34 _reflns_number_total 3513 _reflns_number_gt 3001 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3, 0.98\A, CH2 0.99\A, aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq of the parent atom. 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^)+(0.1066P)^2^+9.3947P] 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 3513 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.2401 _refine_ls_wR_factor_gt 0.2323 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 0.03569(7) 0.86279(10) 0.09710(4) 0.0401(2) Uani 1 1 d . . . C1 C 0.2511(6) 1.3084(8) 0.0750(3) 0.0270(10) Uani 1 1 d . . . Cu2 Cu 0.11209(9) 1.13909(14) 0.03158(6) 0.0439(3) Uani 1 1 d . . . C6 C 0.4615(5) 1.0210(7) 0.2006(3) 0.0238(9) Uani 1 1 d . . . C5 C 0.3331(6) 1.1347(8) 0.2030(4) 0.0285(10) Uani 1 1 d . . . H5A H 0.2525 1.0579 0.1864 0.034 Uiso 1 1 calc R . . H5B H 0.3268 1.1760 0.2604 0.034 Uiso 1 1 calc R . . C8 C 0.5000(6) 0.9040(8) 0.2677(4) 0.0306(11) Uani 1 1 d . . . H8 H 0.4475 0.9000 0.3134 0.037 Uiso 1 1 calc R . . N5 N 0.2871(5) 1.4735(7) 0.0434(3) 0.0311(10) Uani 1 1 d . . . C10 C 0.6156(7) 0.7940(9) 0.2669(4) 0.0382(13) Uani 1 1 d . . . H10 H 0.6397 0.7130 0.3115 0.046 Uiso 1 1 calc R . . N6 N 0.3303(5) 1.2938(7) 0.1484(3) 0.0264(9) Uani 1 1 d . . . C9 C 0.6575(7) 0.9176(10) 0.1349(4) 0.0390(14) Uani 1 1 d . . . H9 H 0.7109 0.9219 0.0897 0.047 Uiso 1 1 calc R . . C11 C 0.6957(7) 0.8024(10) 0.2010(5) 0.0413(15) Uani 1 1 d . . . H11 H 0.7755 0.7300 0.2014 0.050 Uiso 1 1 calc R . . C7 C 0.5414(6) 1.0273(8) 0.1342(4) 0.0310(11) Uani 1 1 d . . . H7 H 0.5168 1.1058 0.0887 0.037 Uiso 1 1 calc R . . C2 C 0.3851(7) 1.5558(9) 0.0970(4) 0.0380(13) Uani 1 1 d . . . H2 H 0.4256 1.6709 0.0893 0.046 Uiso 1 1 calc R . . C4 C 0.2278(8) 1.5475(11) -0.0352(4) 0.0443(16) Uani 1 1 d . . . H4A H 0.2138 1.6786 -0.0295 0.066 Uiso 1 1 calc R . . H4B H 0.1400 1.4884 -0.0513 0.066 Uiso 1 1 calc R . . H4C H 0.2895 1.5254 -0.0776 0.066 Uiso 1 1 calc R . . C3 C 0.4139(6) 1.4442(9) 0.1628(4) 0.0346(12) Uani 1 1 d . . . H3 H 0.4784 1.4650 0.2093 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 Br1 0.0389(4) 0.0509(4) 0.0284(3) 0.0078(2) -0.0072(2) -0.0104(3) C1 0.026(2) 0.030(2) 0.025(2) -0.004(2) 0.0028(18) 0.0019(19) Cu2 0.0361(5) 0.0580(6) 0.0373(5) -0.0089(4) 0.0024(3) 0.0017(4) C6 0.026(2) 0.021(2) 0.023(2) -0.0050(17) 0.0019(17) -0.0047(17) C5 0.023(2) 0.035(3) 0.027(2) 0.001(2) 0.0037(19) -0.0010(19) C8 0.034(3) 0.028(3) 0.029(3) 0.002(2) 0.000(2) -0.007(2) N5 0.035(2) 0.029(2) 0.029(2) -0.0002(18) 0.0048(19) 0.0035(19) C10 0.040(3) 0.028(3) 0.044(3) -0.003(2) -0.007(3) -0.001(2) N6 0.027(2) 0.027(2) 0.025(2) -0.0037(17) 0.0031(16) 0.0015(17) C9 0.038(3) 0.037(3) 0.043(3) -0.010(3) 0.011(3) 0.002(3) C11 0.038(3) 0.034(3) 0.051(4) -0.013(3) -0.002(3) 0.008(3) C7 0.034(3) 0.029(3) 0.031(3) -0.003(2) 0.008(2) -0.002(2) C2 0.047(3) 0.025(3) 0.042(3) -0.004(2) 0.004(3) -0.002(2) C4 0.056(4) 0.043(4) 0.034(3) 0.009(3) 0.004(3) 0.010(3) C3 0.033(3) 0.032(3) 0.038(3) -0.010(2) 0.000(2) -0.003(2) _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 Cu2 2.4249(11) 3_575 ? Br1 Cu2 2.4506(13) . ? C1 N6 1.363(7) . ? C1 N5 1.380(8) . ? C1 Cu2 1.932(6) . ? Cu2 Br1 2.4249(11) 3_575 ? C6 C7 1.403(7) . ? C6 C8 1.411(8) . ? C6 C5 1.522(8) . ? C5 N6 1.468(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C8 C10 1.399(9) . ? C8 H8 0.9500 . ? N5 C2 1.374(9) . ? N5 C4 1.456(8) . ? C10 C11 1.398(11) . ? C10 H10 0.9500 . ? N6 C3 1.386(8) . ? C9 C11 1.390(11) . ? C9 C7 1.400(9) . ? C9 H9 0.9500 . ? C11 H11 0.9500 . ? C7 H7 0.9500 . ? C2 C3 1.356(10) . ? C2 H2 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C3 H3 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 Cu2 Br1 Cu2 79.25(4) 3_575 . ? N6 C1 N5 104.5(5) . . ? N6 C1 Cu2 126.2(4) . . ? N5 C1 Cu2 129.2(4) . . ? C1 Cu2 Br1 131.31(18) . 3_575 ? C1 Cu2 Br1 127.94(18) . . ? Br1 Cu2 Br1 100.75(4) 3_575 . ? C7 C6 C8 119.2(5) . . ? C7 C6 C5 122.5(5) . . ? C8 C6 C5 118.3(5) . . ? N6 C5 C6 112.8(4) . . ? N6 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N6 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C10 C8 C6 120.0(6) . . ? C10 C8 H8 120.0 . . ? C6 C8 H8 120.0 . . ? C2 N5 C1 110.1(5) . . ? C2 N5 C4 125.8(6) . . ? C1 N5 C4 124.1(6) . . ? C11 C10 C8 120.5(6) . . ? C11 C10 H10 119.8 . . ? C8 C10 H10 119.8 . . ? C1 N6 C3 111.2(5) . . ? C1 N6 C5 124.5(5) . . ? C3 N6 C5 124.2(5) . . ? C11 C9 C7 121.0(6) . . ? C11 C9 H9 119.5 . . ? C7 C9 H9 119.5 . . ? C9 C11 C10 119.4(6) . . ? C9 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C9 C7 C6 119.9(6) . . ? C9 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C3 C2 N5 108.1(6) . . ? C3 C2 H2 126.0 . . ? N5 C2 H2 126.0 . . ? N5 C4 H4A 109.5 . . ? N5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C3 N6 106.2(6) . . ? C2 C3 H3 126.9 . . ? N6 C3 H3 126.9 . . ? 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 N6 C1 Cu2 Br1 -178.8(4) . . . 3_575 ? N5 C1 Cu2 Br1 6.0(6) . . . 3_575 ? N6 C1 Cu2 Br1 2.2(6) . . . . ? N5 C1 Cu2 Br1 -173.0(4) . . . . ? Cu2 Br1 Cu2 C1 179.2(2) 3_575 . . . ? Cu2 Br1 Cu2 Br1 0.0 3_575 . . 3_575 ? C7 C6 C5 N6 -21.7(7) . . . . ? C8 C6 C5 N6 159.0(5) . . . . ? C7 C6 C8 C10 -1.0(8) . . . . ? C5 C6 C8 C10 178.4(5) . . . . ? N6 C1 N5 C2 -0.3(6) . . . . ? Cu2 C1 N5 C2 175.8(5) . . . . ? N6 C1 N5 C4 -179.8(6) . . . . ? Cu2 C1 N5 C4 -3.8(9) . . . . ? C6 C8 C10 C11 1.7(9) . . . . ? N5 C1 N6 C3 -0.2(6) . . . . ? Cu2 C1 N6 C3 -176.4(4) . . . . ? N5 C1 N6 C5 -176.7(5) . . . . ? Cu2 C1 N6 C5 7.2(8) . . . . ? C6 C5 N6 C1 105.7(6) . . . . ? C6 C5 N6 C3 -70.4(7) . . . . ? C7 C9 C11 C10 1.1(10) . . . . ? C8 C10 C11 C9 -1.8(10) . . . . ? C11 C9 C7 C6 -0.3(10) . . . . ? C8 C6 C7 C9 0.3(8) . . . . ? C5 C6 C7 C9 -179.1(5) . . . . ? C1 N5 C2 C3 0.6(7) . . . . ? C4 N5 C2 C3 -179.8(6) . . . . ? N5 C2 C3 N6 -0.7(7) . . . . ? C1 N6 C3 C2 0.6(7) . . . . ? C5 N6 C3 C2 177.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.34 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.612 _refine_diff_density_min -2.697 _refine_diff_density_rms 0.206 # Attachment 'web_deposit_cif_file_4_CharlotteWillans_1327938890.BRML95.CIF' data_brml95 _database_code_depnum_ccdc_archive 'CCDC 865140' #TrackingRef 'web_deposit_cif_file_4_CharlotteWillans_1327938890.BRML95.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H40 Cu2 N8, 2(F6 P)' _chemical_formula_sum 'C44 H40 Cu2 F12 N8 P2' _chemical_formula_weight 1097.88 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.7429(13) _cell_length_b 11.0137(17) _cell_length_c 23.226(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.910(4) _cell_angle_gamma 90.00 _cell_volume 2233.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7576 _cell_measurement_theta_min 2.548 _cell_measurement_theta_max 28.366 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 1.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6696 _exptl_absorpt_correction_T_max 0.8592 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_device_type 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 38495 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.38 _reflns_number_total 5563 _reflns_number_gt 4989 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH2 0.99\A, aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. 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^)+(0.0265P)^2^+2.2380P] 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 5563 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.29745(2) 0.52798(2) 0.005293(9) 0.02099(7) Uani 1 1 d . . . N3 N 0.28486(16) 0.48011(14) 0.12903(6) 0.0195(3) Uani 1 1 d . . . N4 N 0.31431(16) 0.31651(13) 0.08179(6) 0.0189(3) Uani 1 1 d . . . N2 N 0.30111(16) 0.57114(14) -0.11874(6) 0.0191(3) Uani 1 1 d . . . C12 C 0.29887(18) 0.43813(16) 0.07491(7) 0.0184(3) Uani 1 1 d . . . C1 C 0.29077(18) 0.61606(16) -0.06496(7) 0.0186(3) Uani 1 1 d . . . C7 C -0.1062(2) 0.37619(16) -0.16985(7) 0.0216(3) Uani 1 1 d . . . N1 N 0.27038(16) 0.73686(13) -0.07315(6) 0.0203(3) Uani 1 1 d . . . C3 C 0.2863(2) 0.66143(18) -0.15957(8) 0.0273(4) Uani 1 1 d . . . H3 H 0.2890 0.6516 -0.2001 0.033 Uiso 1 1 calc R . . C4 C 0.3128(2) 0.44215(17) -0.13354(8) 0.0239(4) Uani 1 1 d . . . H4A H 0.3313 0.3940 -0.0979 0.029 Uiso 1 1 calc R . . H4B H 0.4009 0.4298 -0.1581 0.029 Uiso 1 1 calc R . . C11 C 0.2550(2) 0.82536(17) -0.02711(9) 0.0269(4) Uani 1 1 d . . . H11A H 0.2745 0.9073 -0.0427 0.032 Uiso 1 1 calc R . . H11B H 0.3351 0.8089 0.0036 0.032 Uiso 1 1 calc R . . C5 C 0.16846(19) 0.39848(16) -0.16510(7) 0.0206(3) Uani 1 1 d . . . C15 C 0.3259(2) 0.23136(17) 0.03410(8) 0.0223(3) Uani 1 1 d . . . H15A H 0.3737 0.1554 0.0491 0.027 Uiso 1 1 calc R . . H15B H 0.3945 0.2664 0.0058 0.027 Uiso 1 1 calc R . . C21 C 0.0344(2) 0.20982(16) 0.02959(7) 0.0205(3) Uani 1 1 d . . . H21 H 0.0314 0.2410 0.0677 0.025 Uiso 1 1 calc R . . C16 C 0.17396(19) 0.20046(15) 0.00330(7) 0.0196(3) Uani 1 1 d . . . C6 C 0.0278(2) 0.41262(17) -0.14071(7) 0.0223(3) Uani 1 1 d . . . H6 H 0.0236 0.4478 -0.1035 0.027 Uiso 1 1 calc R . . C13 C 0.2909(2) 0.38689(18) 0.16882(8) 0.0252(4) Uani 1 1 d . . . H13 H 0.2834 0.3942 0.2093 0.030 Uiso 1 1 calc R . . C2 C 0.2672(2) 0.76601(18) -0.13119(8) 0.0273(4) Uani 1 1 d . . . H2 H 0.2542 0.8445 -0.1477 0.033 Uiso 1 1 calc R . . C14 C 0.3094(2) 0.28348(18) 0.13900(8) 0.0247(4) Uani 1 1 d . . . H14 H 0.3175 0.2036 0.1543 0.030 Uiso 1 1 calc R . . P1 P 0.50954(5) 0.42726(5) 0.32793(2) 0.02360(10) Uani 1 1 d . . . F5 F 0.32744(13) 0.42481(13) 0.32594(6) 0.0384(3) Uani 1 1 d . . . F4 F 0.51651(15) 0.32403(11) 0.37656(5) 0.0357(3) Uani 1 1 d . . . F6 F 0.50146(18) 0.53133(14) 0.28005(6) 0.0534(4) Uani 1 1 d . . . F1 F 0.5082(2) 0.52725(12) 0.37794(7) 0.0540(4) Uani 1 1 d . . . F2 F 0.50994(17) 0.32600(14) 0.27900(6) 0.0486(4) Uani 1 1 d . . . F3 F 0.69143(15) 0.43131(19) 0.32975(7) 0.0621(5) Uani 1 1 d . . . C20 C -0.1005(2) 0.17361(16) 0.00015(8) 0.0219(3) Uani 1 1 d . . . C22 C 0.2594(2) 0.60726(17) 0.14392(8) 0.0241(4) Uani 1 1 d . . . H22A H 0.2637 0.6579 0.1088 0.029 Uiso 1 1 calc R . . H22B H 0.3416 0.6347 0.1718 0.029 Uiso 1 1 calc R . . C17 C 0.1773(2) 0.15684(17) -0.05268(8) 0.0254(4) Uani 1 1 d . . . H17 H 0.2719 0.1514 -0.0709 0.030 Uiso 1 1 calc R . . C18 C 0.0424(2) 0.12120(19) -0.08210(8) 0.0312(4) Uani 1 1 d . . . H18 H 0.0448 0.0914 -0.1204 0.037 Uiso 1 1 calc R . . C19 C -0.0951(2) 0.12909(18) -0.05568(8) 0.0282(4) Uani 1 1 d . . . H19 H -0.1869 0.1039 -0.0758 0.034 Uiso 1 1 calc R . . C10 C 0.1747(2) 0.3463(2) -0.21880(9) 0.0415(6) Uani 1 1 d . . . H10 H 0.2705 0.3359 -0.2357 0.050 Uiso 1 1 calc R . . C8 C -0.0990(2) 0.3248(3) -0.22366(10) 0.0470(7) Uani 1 1 d . . . H8 H -0.1904 0.3000 -0.2442 0.056 Uiso 1 1 calc R . . C9 C 0.0409(3) 0.3090(3) -0.24800(12) 0.0662(10) Uani 1 1 d . . . H9 H 0.0452 0.2724 -0.2849 0.079 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 0.02325(11) 0.02259(12) 0.01719(11) 0.00232(8) 0.00168(8) -0.00035(8) N3 0.0145(6) 0.0251(7) 0.0189(7) -0.0022(6) 0.0004(5) -0.0003(6) N4 0.0154(6) 0.0225(7) 0.0186(7) 0.0002(5) 0.0011(5) 0.0011(5) N2 0.0148(6) 0.0227(7) 0.0198(7) 0.0012(6) 0.0013(5) -0.0001(5) C12 0.0132(7) 0.0234(8) 0.0187(8) 0.0001(6) 0.0009(6) -0.0007(6) C1 0.0134(7) 0.0219(8) 0.0204(8) 0.0015(6) 0.0012(6) -0.0002(6) C7 0.0210(8) 0.0208(8) 0.0231(8) -0.0039(7) 0.0022(6) -0.0004(7) N1 0.0162(6) 0.0203(7) 0.0245(7) 0.0010(6) 0.0010(5) -0.0004(5) C3 0.0285(9) 0.0329(10) 0.0205(8) 0.0071(7) 0.0011(7) -0.0030(8) C4 0.0182(8) 0.0261(9) 0.0272(9) -0.0047(7) -0.0006(6) 0.0042(7) C11 0.0201(8) 0.0240(9) 0.0365(10) -0.0080(8) 0.0006(7) -0.0009(7) C5 0.0185(8) 0.0193(8) 0.0238(8) -0.0022(6) 0.0000(6) 0.0023(6) C15 0.0192(8) 0.0247(9) 0.0233(8) -0.0036(7) 0.0028(6) 0.0032(7) C21 0.0205(8) 0.0208(8) 0.0202(8) -0.0020(6) 0.0007(6) 0.0020(7) C16 0.0192(8) 0.0176(8) 0.0220(8) 0.0004(6) 0.0010(6) 0.0024(6) C6 0.0212(8) 0.0272(9) 0.0185(8) -0.0052(7) 0.0013(6) 0.0000(7) C13 0.0233(8) 0.0357(10) 0.0165(8) 0.0035(7) 0.0001(6) 0.0031(8) C2 0.0265(9) 0.0270(9) 0.0282(9) 0.0099(7) -0.0012(7) -0.0036(7) C14 0.0230(8) 0.0296(9) 0.0215(8) 0.0067(7) 0.0016(6) 0.0055(7) P1 0.0218(2) 0.0264(2) 0.0223(2) 0.00378(18) -0.00165(16) -0.00044(18) F5 0.0227(6) 0.0493(8) 0.0429(7) 0.0042(6) 0.0004(5) 0.0026(5) F4 0.0447(7) 0.0313(6) 0.0315(6) 0.0104(5) 0.0064(5) 0.0114(5) F6 0.0524(9) 0.0571(9) 0.0496(8) 0.0338(7) -0.0067(7) -0.0097(7) F1 0.0808(11) 0.0319(7) 0.0473(8) -0.0127(6) -0.0166(8) 0.0000(7) F2 0.0577(9) 0.0580(9) 0.0297(7) -0.0144(6) -0.0011(6) 0.0175(7) F3 0.0220(6) 0.1134(14) 0.0502(9) 0.0282(9) -0.0044(6) -0.0083(8) C20 0.0207(8) 0.0182(8) 0.0266(9) -0.0015(7) -0.0002(6) 0.0028(7) C22 0.0198(8) 0.0249(9) 0.0278(9) -0.0076(7) 0.0041(7) -0.0046(7) C17 0.0280(9) 0.0253(9) 0.0233(9) -0.0021(7) 0.0046(7) 0.0030(7) C18 0.0387(11) 0.0322(10) 0.0224(9) -0.0079(8) -0.0006(8) 0.0019(9) C19 0.0292(9) 0.0264(9) 0.0283(9) -0.0057(7) -0.0070(7) -0.0002(8) C10 0.0227(9) 0.0671(16) 0.0351(11) -0.0247(11) 0.0058(8) 0.0030(10) C8 0.0237(10) 0.0774(18) 0.0397(12) -0.0352(12) -0.0003(8) -0.0026(11) C9 0.0305(12) 0.121(3) 0.0472(15) -0.0574(17) 0.0058(10) -0.0035(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 C12 1.8952(17) . ? Cu1 C1 1.8966(17) . ? N3 C12 1.351(2) . ? N3 C13 1.381(2) . ? N3 C22 1.462(2) . ? N4 C12 1.355(2) . ? N4 C14 1.380(2) . ? N4 C15 1.459(2) . ? N2 C1 1.351(2) . ? N2 C3 1.376(2) . ? N2 C4 1.467(2) . ? C1 N1 1.355(2) . ? C7 C8 1.376(3) . ? C7 C6 1.383(2) . ? C7 C22 1.507(2) 3_565 ? N1 C2 1.385(2) . ? N1 C11 1.458(2) . ? C3 C2 1.342(3) . ? C3 H3 0.9500 . ? C4 C5 1.506(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C11 C20 1.518(2) 3_565 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C5 C10 1.377(3) . ? C5 C6 1.389(2) . ? C15 C16 1.515(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C21 C20 1.391(2) . ? C21 C16 1.396(2) . ? C21 H21 0.9500 . ? C16 C17 1.388(2) . ? C6 H6 0.9500 . ? C13 C14 1.347(3) . ? C13 H13 0.9500 . ? C2 H2 0.9500 . ? C14 H14 0.9500 . ? P1 F3 1.5893(14) . ? P1 F5 1.5907(13) . ? P1 F2 1.5923(14) . ? P1 F6 1.5960(14) . ? P1 F1 1.6011(14) . ? P1 F4 1.6017(12) . ? C20 C19 1.389(3) . ? C20 C11 1.518(2) 3_565 ? C22 C7 1.507(2) 3_565 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C10 C9 1.384(3) . ? C10 H10 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 H9 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 C12 Cu1 C1 178.45(7) . . ? C12 N3 C13 111.48(15) . . ? C12 N3 C22 124.75(15) . . ? C13 N3 C22 123.71(15) . . ? C12 N4 C14 111.49(15) . . ? C12 N4 C15 123.80(15) . . ? C14 N4 C15 124.63(15) . . ? C1 N2 C3 111.36(15) . . ? C1 N2 C4 125.47(15) . . ? C3 N2 C4 122.96(15) . . ? N3 C12 N4 103.99(14) . . ? N3 C12 Cu1 128.19(13) . . ? N4 C12 Cu1 127.82(13) . . ? N2 C1 N1 104.14(14) . . ? N2 C1 Cu1 127.42(13) . . ? N1 C1 Cu1 128.41(13) . . ? C8 C7 C6 119.12(17) . . ? C8 C7 C22 119.71(16) . 3_565 ? C6 C7 C22 121.17(16) . 3_565 ? C1 N1 C2 111.13(15) . . ? C1 N1 C11 124.74(15) . . ? C2 N1 C11 124.13(16) . . ? C2 C3 N2 106.97(16) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? N2 C4 C5 110.89(14) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? N1 C11 C20 115.13(15) . 3_565 ? N1 C11 H11A 108.5 . . ? C20 C11 H11A 108.5 3_565 . ? N1 C11 H11B 108.5 . . ? C20 C11 H11B 108.5 3_565 . ? H11A C11 H11B 107.5 . . ? C10 C5 C6 119.54(17) . . ? C10 C5 C4 120.22(16) . . ? C6 C5 C4 120.23(16) . . ? N4 C15 C16 114.21(14) . . ? N4 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? N4 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C20 C21 C16 120.12(16) . . ? C20 C21 H21 119.9 . . ? C16 C21 H21 119.9 . . ? C17 C16 C21 119.70(16) . . ? C17 C16 C15 117.44(15) . . ? C21 C16 C15 122.81(15) . . ? C7 C6 C5 120.93(16) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C14 C13 N3 106.62(15) . . ? C14 C13 H13 126.7 . . ? N3 C13 H13 126.7 . . ? C3 C2 N1 106.40(16) . . ? C3 C2 H2 126.8 . . ? N1 C2 H2 126.8 . . ? C13 C14 N4 106.41(16) . . ? C13 C14 H14 126.8 . . ? N4 C14 H14 126.8 . . ? F3 P1 F5 179.35(10) . . ? F3 P1 F2 90.01(9) . . ? F5 P1 F2 90.33(8) . . ? F3 P1 F6 90.41(8) . . ? F5 P1 F6 89.04(8) . . ? F2 P1 F6 90.43(9) . . ? F3 P1 F1 90.31(10) . . ? F5 P1 F1 89.35(8) . . ? F2 P1 F1 178.96(9) . . ? F6 P1 F1 90.56(9) . . ? F3 P1 F4 89.94(8) . . ? F5 P1 F4 90.60(7) . . ? F2 P1 F4 90.27(8) . . ? F6 P1 F4 179.22(9) . . ? F1 P1 F4 88.74(7) . . ? C19 C20 C21 119.50(17) . . ? C19 C20 C11 117.40(16) . 3_565 ? C21 C20 C11 123.03(16) . 3_565 ? N3 C22 C7 111.07(14) . 3_565 ? N3 C22 H22A 109.4 . . ? C7 C22 H22A 109.4 3_565 . ? N3 C22 H22B 109.4 . . ? C7 C22 H22B 109.4 3_565 . ? H22A C22 H22B 108.0 . . ? C16 C17 C18 120.08(17) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.03(18) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.55(18) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C5 C10 C9 119.75(19) . . ? C5 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C7 C8 C9 120.33(19) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? 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 C13 N3 C12 N4 -0.19(18) . . . . ? C22 N3 C12 N4 -177.55(14) . . . . ? C13 N3 C12 Cu1 179.83(12) . . . . ? C22 N3 C12 Cu1 2.5(2) . . . . ? C14 N4 C12 N3 0.23(18) . . . . ? C15 N4 C12 N3 177.01(14) . . . . ? C14 N4 C12 Cu1 -179.79(12) . . . . ? C15 N4 C12 Cu1 -3.0(2) . . . . ? C3 N2 C1 N1 -0.50(18) . . . . ? C4 N2 C1 N1 -175.36(14) . . . . ? C3 N2 C1 Cu1 177.84(13) . . . . ? C4 N2 C1 Cu1 3.0(2) . . . . ? N2 C1 N1 C2 0.36(18) . . . . ? Cu1 C1 N1 C2 -177.95(13) . . . . ? N2 C1 N1 C11 -179.14(14) . . . . ? Cu1 C1 N1 C11 2.5(2) . . . . ? C1 N2 C3 C2 0.5(2) . . . . ? C4 N2 C3 C2 175.47(16) . . . . ? C1 N2 C4 C5 110.49(18) . . . . ? C3 N2 C4 C5 -63.8(2) . . . . ? C1 N1 C11 C20 -76.1(2) . . . 3_565 ? C2 N1 C11 C20 104.5(2) . . . 3_565 ? N2 C4 C5 C10 123.3(2) . . . . ? N2 C4 C5 C6 -55.5(2) . . . . ? C12 N4 C15 C16 -79.3(2) . . . . ? C14 N4 C15 C16 97.11(19) . . . . ? C20 C21 C16 C17 1.1(3) . . . . ? C20 C21 C16 C15 -176.36(16) . . . . ? N4 C15 C16 C17 158.00(16) . . . . ? N4 C15 C16 C21 -24.5(2) . . . . ? C8 C7 C6 C5 0.3(3) . . . . ? C22 C7 C6 C5 -179.22(17) 3_565 . . . ? C10 C5 C6 C7 -0.7(3) . . . . ? C4 C5 C6 C7 178.12(17) . . . . ? C12 N3 C13 C14 0.1(2) . . . . ? C22 N3 C13 C14 177.48(15) . . . . ? N2 C3 C2 N1 -0.2(2) . . . . ? C1 N1 C2 C3 -0.1(2) . . . . ? C11 N1 C2 C3 179.41(16) . . . . ? N3 C13 C14 N4 0.06(19) . . . . ? C12 N4 C14 C13 -0.2(2) . . . . ? C15 N4 C14 C13 -176.93(15) . . . . ? C16 C21 C20 C19 -0.5(3) . . . . ? C16 C21 C20 C11 176.53(17) . . . 3_565 ? C12 N3 C22 C7 115.73(18) . . . 3_565 ? C13 N3 C22 C7 -61.3(2) . . . 3_565 ? C21 C16 C17 C18 -0.8(3) . . . . ? C15 C16 C17 C18 176.76(17) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 0.6(3) . . . . ? C21 C20 C19 C18 -0.3(3) . . . . ? C11 C20 C19 C18 -177.56(18) 3_565 . . . ? C6 C5 C10 C9 0.3(4) . . . . ? C4 C5 C10 C9 -178.5(3) . . . . ? C6 C7 C8 C9 0.5(4) . . . . ? C22 C7 C8 C9 -180.0(3) 3_565 . . . ? C5 C10 C9 C8 0.5(5) . . . . ? C7 C8 C9 C10 -0.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.360 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.058