Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;Bulky aryl functionalized carbazolyl ligands: amido alternatives to the 2,6-diarylphenyl ligand class? ; _publ_contact_author_name S.Aldridge _publ_contact_author_email SIMON.ALDRIDGE@CHEM.OX.AC.UK loop_ _publ_author_name S.Aldridge 'Natalie D. Coombs' 'Andrew Cowley' 'Andreas Stasch' 'Amber E. Thompson' # Attachment 'K_dimer.CIF' data_asSA16 _database_code_depnum_ccdc_archive 'CCDC 665746' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H40 K2 N2' _chemical_formula_weight 771.06 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.050(5) _cell_length_b 11.472(5) _cell_length_c 16.097(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 105.146(5) _cell_angle_gamma 90.000(5) _cell_volume 1969.7(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8311 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4287 _reflns_number_gt 3057 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.6731P] 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 4287 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 K1 K 0.41099(5) -0.11930(5) 0.34212(4) 0.04597(17) Uani 1 1 d . . . N1 N 0.45097(14) 0.11278(15) 0.38123(11) 0.0294(4) Uani 1 1 d . . . C1 C 0.57080(17) 0.14206(18) 0.42731(13) 0.0291(5) Uani 1 1 d . . . C2 C 0.68328(17) 0.08569(18) 0.42332(13) 0.0299(5) Uani 1 1 d . . . C3 C 0.79415(17) 0.12352(19) 0.47976(14) 0.0336(5) Uani 1 1 d . . . H3 H 0.8696 0.0838 0.4799 0.040 Uiso 1 1 calc R . . C4 C 0.80018(18) 0.21744(19) 0.53659(14) 0.0339(5) Uani 1 1 d . . . C5 C 0.69046(17) 0.27579(19) 0.53763(13) 0.0323(5) Uani 1 1 d . . . H5 H 0.6930 0.3411 0.5743 0.039 Uiso 1 1 calc R . . C6 C 0.57537(17) 0.23729(18) 0.48381(13) 0.0297(5) Uani 1 1 d . . . C7 C 0.44608(17) 0.27179(18) 0.47184(13) 0.0291(4) Uani 1 1 d . . . C8 C 0.38645(18) 0.35721(18) 0.50864(13) 0.0307(5) Uani 1 1 d . . . H8 H 0.4343 0.4088 0.5508 0.037 Uiso 1 1 calc R . . C9 C 0.25637(18) 0.36614(17) 0.48306(13) 0.0299(5) Uani 1 1 d . . . C10 C 0.18908(17) 0.28759(18) 0.42084(13) 0.0304(5) Uani 1 1 d . . . H10 H 0.1004 0.2947 0.4037 0.036 Uiso 1 1 calc R . . C11 C 0.24331(17) 0.20031(18) 0.38268(12) 0.0284(4) Uani 1 1 d . . . C12 C 0.37646(17) 0.19219(18) 0.40874(13) 0.0280(4) Uani 1 1 d . . . C13 C 0.92554(19) 0.2560(2) 0.59377(17) 0.0473(6) Uani 1 1 d . . . H13A H 0.9800 0.2814 0.5579 0.071 Uiso 1 1 calc R . . H13B H 0.9650 0.1908 0.6302 0.071 Uiso 1 1 calc R . . H13C H 0.9128 0.3209 0.6302 0.071 Uiso 1 1 calc R . . C14 C 0.1889(2) 0.4565(2) 0.52134(15) 0.0400(5) Uani 1 1 d . . . H14A H 0.2501 0.5033 0.5632 0.060 Uiso 1 1 calc R . . H14B H 0.1320 0.4180 0.5502 0.060 Uiso 1 1 calc R . . H14C H 0.1406 0.5073 0.4756 0.060 Uiso 1 1 calc R . . C15 C 0.68018(17) -0.00808(18) 0.35943(13) 0.0307(5) Uani 1 1 d . . . C16 C 0.73122(19) -0.11837(19) 0.38277(15) 0.0367(5) Uani 1 1 d . . . H16 H 0.7700 -0.1349 0.4415 0.044 Uiso 1 1 calc R . . C17 C 0.7259(2) -0.2042(2) 0.32105(16) 0.0430(6) Uani 1 1 d . . . H17 H 0.7608 -0.2788 0.3382 0.052 Uiso 1 1 calc R . . C18 C 0.6706(2) -0.1825(2) 0.23522(16) 0.0435(6) Uani 1 1 d . . . H18 H 0.6685 -0.2413 0.1933 0.052 Uiso 1 1 calc R . . C19 C 0.61805(19) -0.0733(2) 0.21088(15) 0.0393(5) Uani 1 1 d . . . H19 H 0.5789 -0.0578 0.1520 0.047 Uiso 1 1 calc R . . C20 C 0.62254(17) 0.01279(19) 0.27197(13) 0.0337(5) Uani 1 1 d . . . H20 H 0.5862 0.0868 0.2545 0.040 Uiso 1 1 calc R . . C21 C 0.16529(17) 0.11678(18) 0.32109(13) 0.0283(4) Uani 1 1 d . . . C22 C 0.20479(18) 0.0695(2) 0.25234(13) 0.0338(5) Uani 1 1 d . . . H22 H 0.2823 0.0942 0.2431 0.041 Uiso 1 1 calc R . . C23 C 0.13363(19) -0.0122(2) 0.19769(14) 0.0377(5) Uani 1 1 d . . . H23 H 0.1637 -0.0441 0.1524 0.045 Uiso 1 1 calc R . . C24 C 0.01875(19) -0.0479(2) 0.20841(14) 0.0373(5) Uani 1 1 d . . . H24 H -0.0298 -0.1045 0.1711 0.045 Uiso 1 1 calc R . . C25 C -0.02389(19) 0.00017(19) 0.27412(14) 0.0370(5) Uani 1 1 d . . . H25 H -0.1038 -0.0215 0.2808 0.044 Uiso 1 1 calc R . . C26 C 0.04874(18) 0.07966(18) 0.33039(14) 0.0319(5) Uani 1 1 d . . . H26 H 0.0189 0.1097 0.3763 0.038 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 K1 0.0429(3) 0.0441(3) 0.0518(3) 0.0098(3) 0.0141(2) -0.0078(2) N1 0.0202(8) 0.0387(10) 0.0284(9) 0.0020(8) 0.0048(7) 0.0005(7) C1 0.0222(9) 0.0376(12) 0.0269(11) 0.0072(9) 0.0053(8) 0.0008(8) C2 0.0247(10) 0.0339(11) 0.0308(11) 0.0095(9) 0.0067(8) 0.0010(9) C3 0.0198(9) 0.0399(12) 0.0394(12) 0.0135(10) 0.0047(9) 0.0035(9) C4 0.0241(10) 0.0367(12) 0.0377(12) 0.0099(10) 0.0025(9) -0.0035(9) C5 0.0286(10) 0.0323(11) 0.0339(12) 0.0051(10) 0.0042(9) -0.0042(9) C6 0.0240(9) 0.0362(12) 0.0279(11) 0.0069(9) 0.0047(8) -0.0007(9) C7 0.0249(9) 0.0355(11) 0.0259(11) 0.0043(9) 0.0047(8) -0.0018(9) C8 0.0305(10) 0.0337(12) 0.0276(11) 0.0015(9) 0.0069(8) -0.0046(9) C9 0.0306(10) 0.0316(11) 0.0289(11) 0.0038(9) 0.0101(8) 0.0007(9) C10 0.0214(9) 0.0374(12) 0.0321(11) 0.0059(9) 0.0066(8) 0.0008(8) C11 0.0231(9) 0.0379(12) 0.0242(10) 0.0045(9) 0.0061(8) 0.0004(9) C12 0.0242(9) 0.0353(12) 0.0250(10) 0.0048(9) 0.0075(8) 0.0008(9) C13 0.0272(11) 0.0453(14) 0.0606(17) 0.0068(12) -0.0044(10) -0.0059(10) C14 0.0358(11) 0.0363(12) 0.0502(14) -0.0009(11) 0.0153(10) -0.0004(10) C15 0.0191(9) 0.0398(12) 0.0334(11) 0.0106(10) 0.0073(8) -0.0005(8) C16 0.0310(11) 0.0402(13) 0.0372(12) 0.0077(11) 0.0061(9) 0.0041(10) C17 0.0380(12) 0.0372(13) 0.0527(16) 0.0058(12) 0.0099(11) 0.0020(10) C18 0.0378(12) 0.0464(14) 0.0460(15) -0.0067(12) 0.0104(11) -0.0104(11) C19 0.0270(10) 0.0549(15) 0.0343(13) 0.0056(11) 0.0049(9) -0.0091(10) C20 0.0227(10) 0.0419(12) 0.0355(12) 0.0100(10) 0.0059(9) -0.0012(9) C21 0.0213(9) 0.0365(11) 0.0252(10) 0.0046(9) 0.0026(8) 0.0033(8) C22 0.0237(9) 0.0505(13) 0.0260(11) 0.0023(10) 0.0043(8) 0.0002(10) C23 0.0341(11) 0.0498(14) 0.0282(12) -0.0042(10) 0.0064(9) 0.0039(10) C24 0.0316(11) 0.0402(13) 0.0356(12) -0.0028(11) 0.0007(9) -0.0015(10) C25 0.0260(10) 0.0433(13) 0.0408(13) 0.0018(11) 0.0069(9) -0.0029(9) C26 0.0266(10) 0.0375(12) 0.0327(12) -0.0014(9) 0.0098(9) 0.0018(9) _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 K1 N1 2.745(2) . ? K1 C5 3.059(2) 3_656 ? K1 C6 3.080(2) 3_656 ? K1 C15 3.181(2) . ? K1 C22 3.202(2) . ? K1 C20 3.227(2) . ? K1 C16 3.426(3) . ? K1 C7 3.471(2) 3_656 ? K1 C19 3.536(2) . ? N1 C12 1.376(2) . ? N1 C1 1.380(2) . ? C1 C6 1.414(3) . ? C1 C2 1.417(3) . ? C2 C3 1.390(3) . ? C2 C15 1.482(3) . ? C3 C4 1.404(3) . ? C4 C5 1.389(3) . ? C4 C13 1.515(3) . ? C5 C6 1.410(3) . ? C5 K1 3.059(2) 3_656 ? C6 C7 1.446(3) . ? C6 K1 3.080(2) 3_656 ? C7 C8 1.396(3) . ? C7 C12 1.431(3) . ? C7 K1 3.471(2) 3_656 ? C8 C9 1.392(3) . ? C9 C10 1.407(3) . ? C9 C14 1.500(3) . ? C10 C11 1.390(3) . ? C11 C12 1.424(3) . ? C11 C21 1.482(3) . ? C15 C16 1.396(3) . ? C15 C20 1.406(3) . ? C16 C17 1.389(3) . ? C17 C18 1.379(3) . ? C18 C19 1.393(3) . ? C19 C20 1.386(3) . ? C21 C22 1.401(3) . ? C21 C26 1.401(3) . ? C22 C23 1.382(3) . ? C23 C24 1.387(3) . ? C24 C25 1.380(3) . ? C25 C26 1.384(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 K1 C5 119.19(6) . 3_656 ? N1 K1 C6 104.53(6) . 3_656 ? C5 K1 C6 26.55(5) 3_656 3_656 ? N1 K1 C15 60.01(5) . . ? C5 K1 C15 131.97(5) 3_656 . ? C6 K1 C15 105.92(5) 3_656 . ? N1 K1 C22 60.01(6) . . ? C5 K1 C22 110.33(6) 3_656 . ? C6 K1 C22 124.60(6) 3_656 . ? C15 K1 C22 107.88(6) . . ? N1 K1 C20 62.41(5) . . ? C5 K1 C20 156.28(5) 3_656 . ? C6 K1 C20 131.07(5) 3_656 . ? C15 K1 C20 25.33(5) . . ? C22 K1 C20 91.11(6) . . ? N1 K1 C16 81.77(5) . . ? C5 K1 C16 114.32(6) 3_656 . ? C6 K1 C16 91.43(5) 3_656 . ? C15 K1 C16 24.03(5) . . ? C22 K1 C16 131.43(6) . . ? C20 K1 C16 42.19(5) . . ? N1 K1 C7 106.34(5) . 3_656 ? C5 K1 C7 46.99(5) 3_656 3_656 ? C6 K1 C7 24.58(5) 3_656 3_656 ? C15 K1 C7 85.55(5) . 3_656 ? C22 K1 C7 147.14(5) . 3_656 ? C20 K1 C7 109.30(5) . 3_656 ? C16 K1 C7 67.82(5) . 3_656 ? N1 K1 C19 84.37(5) . . ? C5 K1 C19 150.09(6) 3_656 . ? C6 K1 C19 136.35(6) 3_656 . ? C15 K1 C19 41.95(5) . . ? C22 K1 C19 97.16(6) . . ? C20 K1 C19 23.07(5) . . ? C16 K1 C19 46.87(5) . . ? C7 K1 C19 111.78(6) 3_656 . ? C12 N1 C1 103.69(16) . . ? C12 N1 K1 129.92(12) . . ? C1 N1 K1 115.72(12) . . ? N1 C1 C6 113.70(17) . . ? N1 C1 C2 126.46(19) . . ? C6 C1 C2 119.83(18) . . ? C3 C2 C1 117.5(2) . . ? C3 C2 C15 122.46(18) . . ? C1 C2 C15 120.06(17) . . ? C2 C3 C4 123.31(18) . . ? C5 C4 C3 119.00(18) . . ? C5 C4 C13 121.0(2) . . ? C3 C4 C13 120.02(19) . . ? C4 C5 C6 119.5(2) . . ? C4 C5 K1 100.96(13) . 3_656 ? C6 C5 K1 77.53(12) . 3_656 ? C5 C6 C1 120.81(18) . . ? C5 C6 C7 134.2(2) . . ? C1 C6 C7 104.94(17) . . ? C5 C6 K1 75.92(11) . 3_656 ? C1 C6 K1 103.34(13) . 3_656 ? C7 C6 K1 93.06(12) . 3_656 ? C8 C7 C12 121.54(17) . . ? C8 C7 C6 134.02(19) . . ? C12 C7 C6 104.42(18) . . ? C8 C7 K1 98.42(13) . 3_656 ? C12 C7 K1 109.25(13) . 3_656 ? C6 C7 K1 62.36(11) . 3_656 ? C9 C8 C7 119.45(19) . . ? C8 C9 C10 118.45(19) . . ? C8 C9 C14 121.00(19) . . ? C10 C9 C14 120.54(18) . . ? C11 C10 C9 124.57(18) . . ? C10 C11 C12 116.66(18) . . ? C10 C11 C21 121.24(17) . . ? C12 C11 C21 122.03(18) . . ? N1 C12 C11 127.41(18) . . ? N1 C12 C7 113.25(16) . . ? C11 C12 C7 119.33(18) . . ? C16 C15 C20 118.0(2) . . ? C16 C15 C2 122.44(19) . . ? C20 C15 C2 119.57(19) . . ? C16 C15 K1 87.87(12) . . ? C20 C15 K1 79.17(11) . . ? C2 C15 K1 101.74(11) . . ? C17 C16 C15 120.7(2) . . ? C17 C16 K1 90.72(13) . . ? C15 C16 K1 68.10(11) . . ? C18 C17 C16 120.9(2) . . ? C17 C18 C19 119.1(2) . . ? C20 C19 C18 120.4(2) . . ? C20 C19 K1 65.87(11) . . ? C18 C19 K1 89.16(14) . . ? C19 C20 C15 120.8(2) . . ? C19 C20 K1 91.06(12) . . ? C15 C20 K1 75.50(11) . . ? C22 C21 C26 116.85(19) . . ? C22 C21 C11 122.12(17) . . ? C26 C21 C11 121.01(18) . . ? C23 C22 C21 121.51(19) . . ? C23 C22 K1 92.74(14) . . ? C21 C22 K1 103.71(13) . . ? C22 C23 C24 120.6(2) . . ? C25 C24 C23 119.0(2) . . ? C24 C25 C26 120.6(2) . . ? C25 C26 C21 121.5(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.220 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.048 # Attachment '1b.CIF' data_asSA13 _database_code_depnum_ccdc_archive 'CCDC 665747' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33.50 H36.25 N' _chemical_formula_weight 452.89 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9393(16) _cell_length_b 13.589(3) _cell_length_c 25.682(5) _cell_angle_alpha 78.42(3) _cell_angle_beta 81.45(3) _cell_angle_gamma 86.56(3) _cell_volume 2683.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 977 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14902 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9075 _reflns_number_gt 6589 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The solvent ('hexanes') is disordered on an inversion centre and was modelled as a quarter molecule of n-hexane and a quarter molecule of cyclo-hexane in the asymmetric unit. The solvent carbon atoms were refined isotropically. ; _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^)+(0.1024P)^2^+3.3709P] 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 9075 _refine_ls_number_parameters 636 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.2372 _refine_ls_wR_factor_gt 0.2172 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.027 _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 N1 N 0.3379(3) 0.2513(2) 0.87576(10) 0.0353(6) Uani 1 1 d . . . H1 H 0.2815 0.1952 0.8852 0.042 Uiso 1 1 calc R . . C1 C 0.3156(4) 0.3316(2) 0.90230(13) 0.0333(7) Uani 1 1 d . . . N2 N 0.0011(3) 0.67569(19) 0.64894(10) 0.0343(6) Uani 1 1 d . . . H2 H -0.0516 0.7188 0.6259 0.041 Uiso 1 1 calc R . . C2 C 0.2033(4) 0.3410(2) 0.94858(13) 0.0355(8) Uani 1 1 d . . . C3 C 0.2129(4) 0.4287(2) 0.96760(14) 0.0388(8) Uani 1 1 d . . . H3 H 0.1400 0.4374 0.9993 0.047 Uiso 1 1 calc R . . C4 C 0.3255(4) 0.5055(2) 0.94220(14) 0.0388(8) Uani 1 1 d . . . C5 C 0.4309(4) 0.4947(2) 0.89566(14) 0.0381(8) Uani 1 1 d . . . H5 H 0.5054 0.5468 0.8777 0.046 Uiso 1 1 calc R . . C6 C 0.4282(4) 0.4077(2) 0.87513(13) 0.0341(7) Uani 1 1 d . . . C7 C 0.5215(4) 0.3709(2) 0.82945(13) 0.0330(7) Uani 1 1 d . . . C8 C 0.6492(4) 0.4099(2) 0.78797(13) 0.0357(8) Uani 1 1 d . . . H8 H 0.6898 0.4752 0.7857 0.043 Uiso 1 1 calc R . . C9 C 0.7162(4) 0.3527(2) 0.75022(13) 0.0368(8) Uani 1 1 d . . . C10 C 0.6557(4) 0.2565(2) 0.75456(13) 0.0349(8) Uani 1 1 d . . . H10 H 0.7036 0.2183 0.7285 0.042 Uiso 1 1 calc R . . C11 C 0.5290(4) 0.2132(2) 0.79495(12) 0.0322(7) Uani 1 1 d . . . C12 C 0.4637(4) 0.2739(2) 0.83200(12) 0.0319(7) Uani 1 1 d . . . C13 C 0.3276(5) 0.5996(3) 0.96571(16) 0.0523(10) Uani 1 1 d . . . H13A H 0.4098 0.6462 0.9427 0.078 Uiso 1 1 calc R . . H13B H 0.3606 0.5812 1.0018 0.078 Uiso 1 1 calc R . . H13C H 0.2138 0.6320 0.9678 0.078 Uiso 1 1 calc R . . C14 C 0.8537(5) 0.3929(3) 0.70511(15) 0.0482(9) Uani 1 1 d . . . H14A H 0.8480 0.4665 0.6982 0.072 Uiso 1 1 calc R . . H14B H 0.8370 0.3694 0.6726 0.072 Uiso 1 1 calc R . . H14C H 0.9655 0.3688 0.7152 0.072 Uiso 1 1 calc R . . C15 C 0.0838(4) 0.2582(2) 0.97505(13) 0.0363(8) Uani 1 1 d . . . C16 C -0.0598(4) 0.2442(3) 0.95173(14) 0.0400(8) Uani 1 1 d . . . C17 C -0.1684(5) 0.1655(3) 0.97703(15) 0.0443(9) Uani 1 1 d . . . H17 H -0.2652 0.1553 0.9612 0.053 Uiso 1 1 calc R . . C18 C -0.1380(5) 0.1020(3) 1.02462(15) 0.0453(9) Uani 1 1 d . . . C19 C 0.0055(5) 0.1179(3) 1.04639(14) 0.0477(9) Uani 1 1 d . . . H19 H 0.0274 0.0755 1.0790 0.057 Uiso 1 1 calc R . . C20 C 0.1183(5) 0.1934(3) 1.02235(14) 0.0424(8) Uani 1 1 d . . . C21 C -0.1025(5) 0.3111(3) 0.90060(16) 0.0528(10) Uani 1 1 d . . . H21A H 0.0011 0.3222 0.8744 0.079 Uiso 1 1 calc R . . H21B H -0.1496 0.3758 0.9084 0.079 Uiso 1 1 calc R . . H21C H -0.1866 0.2788 0.8858 0.079 Uiso 1 1 calc R . . C22 C -0.2524(6) 0.0161(3) 1.05077(17) 0.0620(12) Uani 1 1 d . . . H22A H -0.2871 0.0191 1.0887 0.093 Uiso 1 1 calc R . . H22B H -0.1908 -0.0477 1.0480 0.093 Uiso 1 1 calc R . . H22C H -0.3537 0.0211 1.0326 0.093 Uiso 1 1 calc R . . C23 C 0.2780(5) 0.2031(3) 1.04610(16) 0.0558(10) Uani 1 1 d . . . H23A H 0.3753 0.2133 1.0174 0.084 Uiso 1 1 calc R . . H23B H 0.2982 0.1417 1.0721 0.084 Uiso 1 1 calc R . . H23C H 0.2643 0.2607 1.0642 0.084 Uiso 1 1 calc R . . C24 C 0.4677(4) 0.1100(2) 0.80033(12) 0.0320(7) Uani 1 1 d . . . C25 C 0.3062(5) 0.0950(2) 0.78759(14) 0.0407(8) Uani 1 1 d . . . C26 C 0.2527(5) -0.0030(3) 0.79459(15) 0.0491(10) Uani 1 1 d . . . H26 H 0.1429 -0.0131 0.7865 0.059 Uiso 1 1 calc R . . C27 C 0.3524(5) -0.0866(3) 0.81289(14) 0.0463(9) Uani 1 1 d . . . C28 C 0.5104(5) -0.0694(3) 0.82488(13) 0.0420(9) Uani 1 1 d . . . H28 H 0.5809 -0.1256 0.8374 0.050 Uiso 1 1 calc R . . C29 C 0.5708(4) 0.0267(2) 0.81939(13) 0.0372(8) Uani 1 1 d . . . C30 C 0.1940(5) 0.1825(3) 0.76568(18) 0.0547(10) Uani 1 1 d . . . H30A H 0.1022 0.1579 0.7505 0.082 Uiso 1 1 calc R . . H30B H 0.2621 0.2294 0.7376 0.082 Uiso 1 1 calc R . . H30C H 0.1448 0.2171 0.7947 0.082 Uiso 1 1 calc R . . C31 C 0.2891(7) -0.1919(3) 0.8212(2) 0.0719(14) Uani 1 1 d . . . H31A H 0.2279 -0.2106 0.8577 0.108 Uiso 1 1 calc R . . H31B H 0.3862 -0.2388 0.8163 0.108 Uiso 1 1 calc R . . H31C H 0.2120 -0.1946 0.7951 0.108 Uiso 1 1 calc R . . C32 C 0.7434(5) 0.0415(3) 0.8352(2) 0.0636(12) Uani 1 1 d . . . H32A H 0.8118 0.0845 0.8053 0.095 Uiso 1 1 calc R . . H32B H 0.8026 -0.0239 0.8438 0.095 Uiso 1 1 calc R . . H32C H 0.7272 0.0733 0.8667 0.095 Uiso 1 1 calc R . . C33 C -0.0258(4) 0.6676(2) 0.70443(12) 0.0312(7) Uani 1 1 d . . . C34 C -0.1431(4) 0.7211(2) 0.73466(13) 0.0330(7) Uani 1 1 d . . . C35 C -0.1454(4) 0.6951(2) 0.79038(13) 0.0370(8) Uani 1 1 d . . . H35 H -0.2241 0.7296 0.8126 0.044 Uiso 1 1 calc R . . C36 C -0.0364(4) 0.6201(2) 0.81495(13) 0.0361(8) Uani 1 1 d . . . C37 C 0.0788(4) 0.5681(2) 0.78315(13) 0.0346(7) Uani 1 1 d . . . H37 H 0.1532 0.5174 0.7992 0.041 Uiso 1 1 calc R . . C38 C 0.0841(4) 0.5910(2) 0.72754(13) 0.0317(7) Uani 1 1 d . . . C39 C 0.1798(4) 0.5501(2) 0.68343(13) 0.0311(7) Uani 1 1 d . . . C40 C 0.3007(4) 0.4708(2) 0.68092(13) 0.0345(7) Uani 1 1 d . . . H40 H 0.3392 0.4339 0.7127 0.041 Uiso 1 1 calc R . . C41 C 0.3629(4) 0.4472(2) 0.63158(14) 0.0357(8) Uani 1 1 d . . . C42 C 0.3062(4) 0.5041(2) 0.58503(13) 0.0358(8) Uani 1 1 d . . . H42 H 0.3518 0.4875 0.5514 0.043 Uiso 1 1 calc R . . C43 C 0.1867(4) 0.5834(2) 0.58555(13) 0.0337(7) Uani 1 1 d . . . C44 C 0.1248(4) 0.6044(2) 0.63609(13) 0.0322(7) Uani 1 1 d . . . C45 C -0.0458(5) 0.5976(3) 0.87541(13) 0.0452(9) Uani 1 1 d . . . H45A H 0.0387 0.5446 0.8860 0.068 Uiso 1 1 calc R . . H45B H -0.1601 0.5751 0.8917 0.068 Uiso 1 1 calc R . . H45C H -0.0223 0.6585 0.8877 0.068 Uiso 1 1 calc R . . C46 C 0.4888(5) 0.3603(3) 0.62646(15) 0.0446(9) Uani 1 1 d . . . H46A H 0.5182 0.3294 0.6620 0.067 Uiso 1 1 calc R . . H46B H 0.5921 0.3850 0.6027 0.067 Uiso 1 1 calc R . . H46C H 0.4376 0.3103 0.6114 0.067 Uiso 1 1 calc R . . C47 C -0.2592(4) 0.8016(2) 0.70953(13) 0.0345(8) Uani 1 1 d . . . C48 C -0.4097(5) 0.7778(3) 0.69389(18) 0.0540(10) Uani 1 1 d . . . C49 C -0.5160(5) 0.8552(3) 0.6714(2) 0.0676(13) Uani 1 1 d . . . H49 H -0.6183 0.8383 0.6607 0.081 Uiso 1 1 calc R . . C50 C -0.4788(5) 0.9541(3) 0.66417(16) 0.0524(10) Uani 1 1 d . . . C51 C -0.3260(5) 0.9766(3) 0.67857(15) 0.0476(9) Uani 1 1 d . . . H51 H -0.2966 1.0450 0.6732 0.057 Uiso 1 1 calc R . . C52 C -0.2147(5) 0.9026(3) 0.70057(14) 0.0416(8) Uani 1 1 d . . . C53 C -0.4592(6) 0.6687(3) 0.7015(3) 0.0908(19) Uani 1 1 d . . . H53A H -0.4993 0.6431 0.7396 0.136 Uiso 1 1 calc R . . H53B H -0.3598 0.6282 0.6897 0.136 Uiso 1 1 calc R . . H53C H -0.5502 0.6645 0.6802 0.136 Uiso 1 1 calc R . . C54 C -0.5972(6) 1.0371(4) 0.6410(2) 0.0780(15) Uani 1 1 d . . . H54A H -0.5309 1.0874 0.6143 0.117 Uiso 1 1 calc R . . H54B H -0.6574 1.0689 0.6698 0.117 Uiso 1 1 calc R . . H54C H -0.6801 1.0090 0.6237 0.117 Uiso 1 1 calc R . . C55 C -0.0518(7) 0.9297(3) 0.7155(2) 0.0808(16) Uani 1 1 d . . . H55A H 0.0442 0.8994 0.6949 0.121 Uiso 1 1 calc R . . H55B H -0.0496 0.9046 0.7539 0.121 Uiso 1 1 calc R . . H55C H -0.0428 1.0029 0.7075 0.121 Uiso 1 1 calc R . . C56 C 0.1258(4) 0.6400(2) 0.53526(13) 0.0358(8) Uani 1 1 d . . . C57 C -0.0369(4) 0.6232(2) 0.52349(13) 0.0368(8) Uani 1 1 d . . . C58 C -0.0854(5) 0.6746(3) 0.47510(14) 0.0422(8) Uani 1 1 d . . . H58 H -0.1947 0.6636 0.4669 0.051 Uiso 1 1 calc R . . C59 C 0.0204(5) 0.7412(3) 0.43847(13) 0.0417(9) Uani 1 1 d . . . C60 C 0.1784(5) 0.7572(3) 0.45109(14) 0.0445(9) Uani 1 1 d . . . H60 H 0.2516 0.8030 0.4264 0.053 Uiso 1 1 calc R . . C61 C 0.2338(4) 0.7082(3) 0.49900(14) 0.0413(8) Uani 1 1 d . . . C62 C -0.1570(5) 0.5507(3) 0.56117(14) 0.0449(9) Uani 1 1 d . . . H62A H -0.2526 0.5399 0.5431 0.067 Uiso 1 1 calc R . . H62B H -0.2001 0.5785 0.5931 0.067 Uiso 1 1 calc R . . H62C H -0.0962 0.4865 0.5718 0.067 Uiso 1 1 calc R . . C63 C -0.0374(6) 0.7958(3) 0.38625(15) 0.0563(11) Uani 1 1 d . . . H63A H -0.1199 0.7552 0.3758 0.084 Uiso 1 1 calc R . . H63B H 0.0613 0.8065 0.3581 0.084 Uiso 1 1 calc R . . H63C H -0.0908 0.8608 0.3911 0.084 Uiso 1 1 calc R . . C64 C 0.4067(5) 0.7300(3) 0.51129(17) 0.0583(11) Uani 1 1 d . . . H64A H 0.4819 0.6702 0.5109 0.087 Uiso 1 1 calc R . . H64B H 0.3943 0.7478 0.5468 0.087 Uiso 1 1 calc R . . H64C H 0.4559 0.7860 0.4841 0.087 Uiso 1 1 calc R . . C65 C -1.2891(13) 0.8579(7) 0.5522(4) 0.076(3) Uiso 0.50 1 d PD A 1 H65A H -1.3017 0.8088 0.5299 0.114 Uiso 0.50 1 calc PR A 1 H65B H -1.3982 0.8679 0.5743 0.114 Uiso 0.50 1 calc PR A 1 H65C H -1.2025 0.8329 0.5756 0.114 Uiso 0.50 1 calc PR A 1 C67 C -1.0419(18) 0.9836(12) 0.5213(6) 0.116(5) Uiso 0.50 1 d PD . 1 H67A H -1.0500 1.0352 0.5439 0.140 Uiso 0.50 1 calc PR . 1 H67B H -0.9796 0.9243 0.5394 0.140 Uiso 0.50 1 calc PR . 1 C66 C -1.239(2) 0.9500(13) 0.5189(8) 0.169(7) Uiso 0.50 1 d PD A 1 H66A H -1.3196 1.0036 0.5289 0.203 Uiso 0.50 1 calc PR A 1 H66B H -1.2479 0.9461 0.4814 0.203 Uiso 0.50 1 calc PR A 1 C68 C -1.1185(13) 0.9002(8) 0.5474(4) 0.075(3) Uiso 0.50 1 d PD . 2 H68A H -1.1133 0.8322 0.5387 0.090 Uiso 0.50 1 calc PR . 2 H68B H -1.2117 0.9054 0.5770 0.090 Uiso 0.50 1 calc PR . 2 C70 C -0.870(3) 1.0063(14) 0.5076(7) 0.149(6) Uiso 0.50 1 d PD . 2 H70A H -0.8178 0.9543 0.4877 0.179 Uiso 0.50 1 calc PR . 2 H70B H -0.7712 1.0324 0.5195 0.179 Uiso 0.50 1 calc PR . 2 C69 C -0.926(2) 0.9352(16) 0.5596(8) 0.202(9) Uiso 0.50 1 d PD B 2 H69A H -0.9390 0.9695 0.5906 0.242 Uiso 0.50 1 calc PR B 2 H69B H -0.8449 0.8770 0.5658 0.242 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0423(16) 0.0278(14) 0.0355(15) -0.0096(12) 0.0017(12) -0.0053(12) C1 0.0401(18) 0.0261(17) 0.0344(18) -0.0071(14) -0.0075(14) 0.0036(14) N2 0.0404(16) 0.0288(14) 0.0330(15) -0.0062(11) -0.0058(12) 0.0073(12) C2 0.0418(19) 0.0307(18) 0.0345(18) -0.0081(14) -0.0068(14) 0.0051(14) C3 0.047(2) 0.0353(19) 0.0363(19) -0.0112(15) -0.0102(15) 0.0063(15) C4 0.045(2) 0.0303(18) 0.045(2) -0.0136(15) -0.0137(16) 0.0068(15) C5 0.044(2) 0.0260(17) 0.047(2) -0.0086(15) -0.0136(16) 0.0006(14) C6 0.0387(18) 0.0254(17) 0.0389(18) -0.0048(14) -0.0099(14) -0.0006(14) C7 0.0358(17) 0.0265(17) 0.0371(18) -0.0056(14) -0.0068(14) -0.0016(13) C8 0.0410(19) 0.0247(17) 0.0413(19) -0.0033(14) -0.0091(15) -0.0021(14) C9 0.0339(18) 0.0353(19) 0.0390(19) -0.0018(15) -0.0046(14) -0.0038(14) C10 0.0378(18) 0.0324(18) 0.0338(18) -0.0082(14) -0.0010(14) -0.0003(14) C11 0.0369(18) 0.0270(17) 0.0331(17) -0.0066(13) -0.0056(14) -0.0001(13) C12 0.0347(17) 0.0294(17) 0.0309(17) -0.0052(13) -0.0031(13) -0.0004(13) C13 0.063(3) 0.042(2) 0.060(2) -0.0256(19) -0.015(2) 0.0023(18) C14 0.048(2) 0.045(2) 0.048(2) -0.0068(17) 0.0058(17) -0.0128(17) C15 0.0426(19) 0.0301(18) 0.0355(18) -0.0104(14) -0.0006(15) 0.0054(14) C16 0.044(2) 0.0371(19) 0.0385(19) -0.0122(15) -0.0003(15) 0.0042(15) C17 0.043(2) 0.043(2) 0.047(2) -0.0170(17) 0.0025(16) -0.0031(16) C18 0.052(2) 0.038(2) 0.044(2) -0.0135(17) 0.0092(17) -0.0041(16) C19 0.065(3) 0.041(2) 0.0339(19) -0.0035(16) 0.0002(17) 0.0012(18) C20 0.051(2) 0.038(2) 0.0368(19) -0.0095(16) -0.0033(16) 0.0029(16) C21 0.053(2) 0.053(2) 0.053(2) -0.0040(19) -0.0181(19) -0.0035(19) C22 0.068(3) 0.051(3) 0.060(3) -0.010(2) 0.016(2) -0.013(2) C23 0.067(3) 0.052(2) 0.048(2) -0.0044(19) -0.019(2) 0.003(2) C24 0.0377(18) 0.0292(17) 0.0293(17) -0.0090(13) -0.0005(13) -0.0023(14) C25 0.051(2) 0.0307(19) 0.043(2) -0.0088(15) -0.0107(16) -0.0024(16) C26 0.057(2) 0.040(2) 0.055(2) -0.0088(18) -0.0212(19) -0.0119(18) C27 0.068(3) 0.0310(19) 0.043(2) -0.0122(16) -0.0097(18) -0.0053(18) C28 0.058(2) 0.0290(19) 0.0365(19) -0.0073(15) -0.0011(16) 0.0096(16) C29 0.0403(19) 0.0318(18) 0.0373(18) -0.0061(14) -0.0006(15) 0.0030(14) C30 0.052(2) 0.044(2) 0.070(3) -0.005(2) -0.024(2) -0.0040(18) C31 0.110(4) 0.033(2) 0.078(3) -0.009(2) -0.027(3) -0.018(2) C32 0.044(2) 0.048(2) 0.092(3) 0.009(2) -0.017(2) 0.0006(19) C33 0.0361(17) 0.0264(17) 0.0323(17) -0.0084(13) -0.0048(13) -0.0006(13) C34 0.0351(17) 0.0263(17) 0.0378(18) -0.0074(14) -0.0042(14) -0.0012(13) C35 0.0409(19) 0.0312(18) 0.0397(19) -0.0123(15) -0.0011(15) 0.0002(14) C36 0.0410(19) 0.0335(18) 0.0349(18) -0.0088(14) -0.0064(14) -0.0007(15) C37 0.0372(18) 0.0291(17) 0.0387(19) -0.0060(14) -0.0106(14) 0.0000(14) C38 0.0322(17) 0.0276(17) 0.0363(18) -0.0080(14) -0.0061(13) -0.0005(13) C39 0.0297(16) 0.0275(17) 0.0370(18) -0.0078(14) -0.0063(13) -0.0002(13) C40 0.0321(17) 0.0311(18) 0.0401(19) -0.0053(14) -0.0072(14) 0.0009(14) C41 0.0307(17) 0.0317(18) 0.045(2) -0.0101(15) -0.0047(14) 0.0009(14) C42 0.0348(18) 0.0356(19) 0.0372(18) -0.0099(15) -0.0028(14) 0.0012(14) C43 0.0344(17) 0.0324(18) 0.0333(17) -0.0054(14) -0.0036(14) 0.0019(14) C44 0.0301(16) 0.0273(17) 0.0397(18) -0.0085(14) -0.0053(14) 0.0029(13) C45 0.058(2) 0.043(2) 0.0361(19) -0.0102(16) -0.0103(17) 0.0032(17) C46 0.044(2) 0.041(2) 0.047(2) -0.0087(17) -0.0067(16) 0.0110(16) C47 0.0367(18) 0.0299(18) 0.0358(18) -0.0082(14) -0.0010(14) 0.0039(14) C48 0.037(2) 0.036(2) 0.085(3) 0.000(2) -0.0124(19) -0.0007(16) C49 0.041(2) 0.049(3) 0.108(4) 0.005(2) -0.025(2) 0.0026(19) C50 0.046(2) 0.043(2) 0.061(3) 0.0026(18) -0.0032(19) 0.0108(18) C51 0.068(3) 0.0269(19) 0.046(2) -0.0055(16) -0.0055(18) 0.0072(17) C52 0.055(2) 0.0331(19) 0.0390(19) -0.0100(15) -0.0104(16) 0.0007(16) C53 0.060(3) 0.043(3) 0.171(6) 0.001(3) -0.048(3) -0.010(2) C54 0.063(3) 0.058(3) 0.098(4) 0.013(3) -0.011(3) 0.020(2) C55 0.100(4) 0.038(2) 0.113(4) 0.003(2) -0.062(3) -0.019(2) C56 0.0372(18) 0.0339(18) 0.0360(18) -0.0102(14) -0.0029(14) 0.0082(14) C57 0.0391(19) 0.0343(18) 0.0378(19) -0.0108(15) -0.0057(15) 0.0067(14) C58 0.044(2) 0.041(2) 0.042(2) -0.0094(16) -0.0103(16) 0.0114(16) C59 0.049(2) 0.040(2) 0.0341(18) -0.0083(15) -0.0040(16) 0.0153(16) C60 0.048(2) 0.040(2) 0.039(2) -0.0035(16) 0.0020(16) 0.0095(17) C61 0.0390(19) 0.042(2) 0.040(2) -0.0053(16) -0.0018(15) 0.0069(16) C62 0.043(2) 0.048(2) 0.043(2) -0.0076(17) -0.0064(16) 0.0016(17) C63 0.067(3) 0.055(3) 0.042(2) -0.0022(18) -0.0108(19) 0.018(2) C64 0.045(2) 0.062(3) 0.061(3) 0.004(2) -0.0050(19) -0.0055(19) _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 N1 C12 1.386(4) . ? N1 C1 1.388(4) . ? C1 C2 1.398(4) . ? C1 C6 1.411(5) . ? N2 C44 1.389(4) . ? N2 C33 1.392(4) . ? C2 C3 1.386(5) . ? C2 C15 1.503(5) . ? C3 C4 1.407(5) . ? C4 C5 1.382(5) . ? C4 C13 1.522(5) . ? C5 C6 1.391(4) . ? C6 C7 1.451(5) . ? C7 C8 1.400(5) . ? C7 C12 1.408(4) . ? C8 C9 1.388(5) . ? C9 C10 1.399(5) . ? C9 C14 1.507(5) . ? C10 C11 1.396(4) . ? C11 C12 1.403(4) . ? C11 C24 1.487(4) . ? C15 C20 1.402(5) . ? C15 C16 1.403(5) . ? C16 C17 1.405(5) . ? C16 C21 1.511(5) . ? C17 C18 1.391(5) . ? C18 C19 1.387(6) . ? C18 C22 1.507(5) . ? C19 C20 1.388(5) . ? C20 C23 1.510(5) . ? C24 C25 1.405(5) . ? C24 C29 1.406(5) . ? C25 C26 1.391(5) . ? C25 C30 1.509(5) . ? C26 C27 1.388(5) . ? C27 C28 1.379(5) . ? C27 C31 1.509(5) . ? C28 C29 1.391(5) . ? C29 C32 1.522(5) . ? C33 C34 1.389(4) . ? C33 C38 1.412(4) . ? C34 C35 1.401(5) . ? C34 C47 1.495(4) . ? C35 C36 1.409(5) . ? C36 C37 1.391(5) . ? C36 C45 1.513(5) . ? C37 C38 1.394(4) . ? C38 C39 1.454(4) . ? C39 C44 1.405(4) . ? C39 C40 1.404(4) . ? C40 C41 1.382(5) . ? C41 C42 1.406(5) . ? C41 C46 1.514(4) . ? C42 C43 1.394(4) . ? C43 C44 1.397(4) . ? C43 C56 1.495(5) . ? C47 C48 1.391(5) . ? C47 C52 1.403(5) . ? C48 C49 1.395(5) . ? C48 C53 1.524(6) . ? C49 C50 1.364(6) . ? C50 C51 1.388(6) . ? C50 C54 1.510(5) . ? C51 C52 1.388(5) . ? C52 C55 1.489(6) . ? C56 C61 1.405(5) . ? C56 C57 1.411(5) . ? C57 C58 1.394(5) . ? C57 C62 1.507(5) . ? C58 C59 1.387(5) . ? C59 C60 1.381(5) . ? C59 C63 1.517(5) . ? C60 C61 1.396(5) . ? C61 C64 1.512(5) . ? C65 C66 1.410(15) . ? C67 C67 1.21(3) 2_376 ? C67 C66 1.666(16) . ? C68 C70 1.71(2) 2_376 ? C68 C69 1.722(16) . ? C70 C69 1.507(16) . ? C70 C68 1.71(2) 2_376 ? 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 N1 C1 108.8(3) . . ? N1 C1 C2 128.3(3) . . ? N1 C1 C6 109.0(3) . . ? C2 C1 C6 122.6(3) . . ? C44 N2 C33 108.6(3) . . ? C3 C2 C1 115.9(3) . . ? C3 C2 C15 124.0(3) . . ? C1 C2 C15 120.1(3) . . ? C2 C3 C4 123.1(3) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 C13 121.0(3) . . ? C3 C4 C13 119.8(3) . . ? C4 C5 C6 120.1(3) . . ? C5 C6 C1 119.0(3) . . ? C5 C6 C7 134.6(3) . . ? C1 C6 C7 106.4(3) . . ? C8 C7 C12 119.0(3) . . ? C8 C7 C6 134.2(3) . . ? C12 C7 C6 106.7(3) . . ? C9 C8 C7 119.7(3) . . ? C8 C9 C10 119.2(3) . . ? C8 C9 C14 120.8(3) . . ? C10 C9 C14 119.9(3) . . ? C11 C10 C9 123.9(3) . . ? C10 C11 C12 115.0(3) . . ? C10 C11 C24 123.8(3) . . ? C12 C11 C24 121.1(3) . . ? N1 C12 C11 127.9(3) . . ? N1 C12 C7 109.0(3) . . ? C11 C12 C7 123.1(3) . . ? C20 C15 C16 120.1(3) . . ? C20 C15 C2 119.9(3) . . ? C16 C15 C2 120.0(3) . . ? C15 C16 C17 118.8(3) . . ? C15 C16 C21 122.4(3) . . ? C17 C16 C21 118.8(3) . . ? C18 C17 C16 121.8(4) . . ? C19 C18 C17 117.8(3) . . ? C19 C18 C22 120.7(4) . . ? C17 C18 C22 121.5(4) . . ? C18 C19 C20 122.6(3) . . ? C19 C20 C15 119.0(4) . . ? C19 C20 C23 120.2(3) . . ? C15 C20 C23 120.9(3) . . ? C25 C24 C29 119.8(3) . . ? C25 C24 C11 120.5(3) . . ? C29 C24 C11 119.7(3) . . ? C26 C25 C24 118.4(3) . . ? C26 C25 C30 120.3(3) . . ? C24 C25 C30 121.3(3) . . ? C27 C26 C25 123.0(4) . . ? C28 C27 C26 117.2(3) . . ? C28 C27 C31 121.1(4) . . ? C26 C27 C31 121.7(4) . . ? C27 C28 C29 122.7(3) . . ? C28 C29 C24 118.9(3) . . ? C28 C29 C32 120.6(3) . . ? C24 C29 C32 120.5(3) . . ? C34 C33 N2 128.0(3) . . ? C34 C33 C38 123.0(3) . . ? N2 C33 C38 108.9(3) . . ? C33 C34 C35 115.7(3) . . ? C33 C34 C47 122.3(3) . . ? C35 C34 C47 122.0(3) . . ? C34 C35 C36 123.0(3) . . ? C37 C36 C35 119.4(3) . . ? C37 C36 C45 121.0(3) . . ? C35 C36 C45 119.5(3) . . ? C36 C37 C38 119.4(3) . . ? C37 C38 C33 119.4(3) . . ? C37 C38 C39 134.1(3) . . ? C33 C38 C39 106.5(3) . . ? C44 C39 C40 119.8(3) . . ? C44 C39 C38 106.7(3) . . ? C40 C39 C38 133.4(3) . . ? C41 C40 C39 119.1(3) . . ? C40 C41 C42 119.4(3) . . ? C40 C41 C46 121.6(3) . . ? C42 C41 C46 119.0(3) . . ? C43 C42 C41 123.5(3) . . ? C42 C43 C44 115.6(3) . . ? C42 C43 C56 121.8(3) . . ? C44 C43 C56 122.5(3) . . ? N2 C44 C43 128.2(3) . . ? N2 C44 C39 109.2(3) . . ? C43 C44 C39 122.5(3) . . ? C48 C47 C52 119.3(3) . . ? C48 C47 C34 121.0(3) . . ? C52 C47 C34 119.7(3) . . ? C47 C48 C49 119.2(4) . . ? C47 C48 C53 120.6(3) . . ? C49 C48 C53 120.2(4) . . ? C50 C49 C48 122.6(4) . . ? C49 C50 C51 117.6(3) . . ? C49 C50 C54 122.0(4) . . ? C51 C50 C54 120.4(4) . . ? C52 C51 C50 122.2(3) . . ? C51 C52 C47 119.1(3) . . ? C51 C52 C55 120.6(3) . . ? C47 C52 C55 120.3(3) . . ? C61 C56 C57 120.1(3) . . ? C61 C56 C43 119.4(3) . . ? C57 C56 C43 120.4(3) . . ? C58 C57 C56 118.4(3) . . ? C58 C57 C62 119.6(3) . . ? C56 C57 C62 122.0(3) . . ? C59 C58 C57 122.3(3) . . ? C60 C59 C58 118.3(3) . . ? C60 C59 C63 121.1(3) . . ? C58 C59 C63 120.6(3) . . ? C59 C60 C61 122.1(3) . . ? C60 C61 C56 118.8(3) . . ? C60 C61 C64 119.9(3) . . ? C56 C61 C64 121.3(3) . . ? C67 C67 C66 116(2) 2_376 . ? C65 C66 C67 115.7(14) . . ? C70 C68 C69 94.8(10) 2_376 . ? C69 C70 C68 159.5(17) . 2_376 ? C70 C69 C68 100.4(15) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.451 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.055 # Attachment '3b.cif' data_5397 _database_code_depnum_ccdc_archive 'CCDC 665748' _chemical_name_systematic ? _chemical_melting_point ? _refine_special_details ; All hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been previously identified by examination of a difference Fourier map. ; _cell_length_a 17.6105(3) _cell_length_b 7.9618(2) _cell_length_c 20.3758(4) _cell_angle_alpha 90 _cell_angle_beta 104.6988(7) _cell_angle_gamma 90 _cell_volume 2763.42(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ga 0.2307 1.6083 15.2354 3.0669 6.7006 0.2412 4.3591 10.7805 2.9623 61.4135 1.7189 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C32 H32 Cl2 Ga1 N1' _chemical_formula_moiety 'C32 H32 Cl2 Ga1 N1' _chemical_compound_source 'synthesis as described' _chemical_formula_weight 571.24 _cell_measurement_reflns_used 29657 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description fragment _exptl_crystal_colour 'pale blue' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.78 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 29657 _reflns_number_total 6288 #6730 unique reflectuions including absences _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_theta_min 5.121 _diffrn_reflns_theta_max 27.496 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.671 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -22 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.26 _refine_diff_density_max 0.77 _refine_ls_number_reflns 3990 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 #_refine_ls_R_factor_ref 0.0459 _refine_ls_wR_factor_ref 0.0535 _refine_ls_goodness_of_fit_ref 1.0837 #_reflns_number_all 6288 _refine_ls_R_factor_all 0.0779 _refine_ls_wR_factor_all 0.0773 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3990 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_gt 0.0535 _refine_ls_shift/su_max 0.002913 _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.788 0.491 0.452 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Ga1 Ga 0.28097(2) 0.38264(5) 0.24654(2) 0.0386 1.0000 Uani Cl1 Cl 0.24177(6) 0.63339(11) 0.22305(5) 0.0435 1.0000 Uani Cl2 Cl 0.39981(5) 0.36726(12) 0.30159(5) 0.0407 1.0000 Uani N1 N 0.20930(14) 0.2085(3) 0.23684(12) 0.0217 1.0000 Uani C1 C 0.15632(16) 0.1689(3) 0.27600(15) 0.0201 1.0000 Uani C2 C 0.15744(16) 0.2245(4) 0.34114(15) 0.0214 1.0000 Uani C3 C 0.09836(16) 0.1606(4) 0.36968(15) 0.0227 1.0000 Uani C4 C 0.04206(16) 0.0444(4) 0.33623(15) 0.0227 1.0000 Uani C5 C 0.04332(15) -0.0105(3) 0.27166(16) 0.0216 1.0000 Uani C6 C 0.09967(16) 0.0526(4) 0.24105(15) 0.0214 1.0000 Uani C7 C 0.11693(16) 0.0216(4) 0.17642(15) 0.0218 1.0000 Uani C8 C 0.08268(17) -0.0767(4) 0.12009(16) 0.0252 1.0000 Uani C9 C 0.11509(18) -0.0786(4) 0.06479(16) 0.0286 1.0000 Uani C10 C 0.18275(19) 0.0164(4) 0.06645(16) 0.0300 1.0000 Uani C11 C 0.21904(16) 0.1147(4) 0.12231(15) 0.0253 1.0000 Uani C12 C 0.18426(16) 0.1183(4) 0.17655(14) 0.0222 1.0000 Uani C13 C 0.22164(16) 0.3348(4) 0.38027(15) 0.0201 1.0000 Uani C14 C 0.29108(17) 0.2601(4) 0.41844(16) 0.0229 1.0000 Uani C15 C 0.35018(17) 0.3597(4) 0.45732(16) 0.0262 1.0000 Uani C16 C 0.34283(18) 0.5342(4) 0.45805(16) 0.0270 1.0000 Uani C17 C 0.27414(18) 0.6062(4) 0.41957(17) 0.0291 1.0000 Uani C18 C 0.21258(17) 0.5098(4) 0.38112(15) 0.0232 1.0000 Uani C19 C 0.30255(19) 0.0727(4) 0.41696(19) 0.0314 1.0000 Uani C20 C 0.4089(2) 0.6411(4) 0.4982(2) 0.0428 1.0000 Uani C21 C 0.13714(19) 0.5936(4) 0.34256(18) 0.0335 1.0000 Uani C22 C -0.01964(18) -0.0216(4) 0.36911(17) 0.0289 1.0000 Uani C23 C 0.0776(2) -0.1820(5) 0.00279(18) 0.0374 1.0000 Uani C24 C 0.29291(18) 0.2107(4) 0.12684(15) 0.0262 1.0000 Uani C25 C 0.29020(18) 0.3766(4) 0.10288(16) 0.0297 1.0000 Uani C26 C 0.3613(2) 0.4596(5) 0.10593(18) 0.0347 1.0000 Uani C27 C 0.43288(19) 0.3805(5) 0.12888(18) 0.0350 1.0000 Uani C28 C 0.43424(19) 0.2156(5) 0.15215(18) 0.0332 1.0000 Uani C29 C 0.36575(18) 0.1295(4) 0.15207(17) 0.0309 1.0000 Uani C30 C 0.2130(2) 0.4593(5) 0.06854(19) 0.0397 1.0000 Uani C31 C 0.5080(2) 0.4722(6) 0.1298(3) 0.0571 1.0000 Uani C32 C 0.3689(2) -0.0478(5) 0.1786(2) 0.0490 1.0000 Uani H31 H 0.0966 0.2000 0.4159 0.0276 1.0000 Uiso H51 H 0.0040 -0.0948 0.2474 0.0254 1.0000 Uiso H81 H 0.0350 -0.1454 0.1196 0.0293 1.0000 Uiso H101 H 0.2057 0.0135 0.0263 0.0362 1.0000 Uiso H151 H 0.3989 0.3056 0.4853 0.0313 1.0000 Uiso H171 H 0.2686 0.7312 0.4194 0.0344 1.0000 Uiso H191 H 0.3551 0.0425 0.4470 0.0375 1.0000 Uiso H192 H 0.2605 0.0150 0.4335 0.0375 1.0000 Uiso H193 H 0.2997 0.0361 0.3694 0.0375 1.0000 Uiso H201 H 0.3934 0.7622 0.4928 0.0479 1.0000 Uiso H202 H 0.4204 0.6094 0.5472 0.0479 1.0000 Uiso H203 H 0.4568 0.6229 0.4812 0.0479 1.0000 Uiso H211 H 0.1419 0.7179 0.3493 0.0388 1.0000 Uiso H212 H 0.0924 0.5509 0.3598 0.0388 1.0000 Uiso H213 H 0.1274 0.5671 0.2931 0.0388 1.0000 Uiso H221 H -0.0122 0.0303 0.4150 0.0358 1.0000 Uiso H222 H -0.0147 -0.1464 0.3738 0.0358 1.0000 Uiso H223 H -0.0730 0.0075 0.3403 0.0358 1.0000 Uiso H231 H 0.1084 -0.1688 -0.0319 0.0440 1.0000 Uiso H232 H 0.0770 -0.3029 0.0159 0.0440 1.0000 Uiso H233 H 0.0225 -0.1425 -0.0166 0.0440 1.0000 Uiso H261 H 0.3601 0.5794 0.0911 0.0432 1.0000 Uiso H281 H 0.4859 0.1579 0.1693 0.0401 1.0000 Uiso H301 H 0.2230 0.5765 0.0551 0.0476 1.0000 Uiso H302 H 0.1785 0.4625 0.1006 0.0476 1.0000 Uiso H303 H 0.1866 0.3937 0.0272 0.0476 1.0000 Uiso H311 H 0.5537 0.3962 0.1479 0.0694 1.0000 Uiso H312 H 0.5125 0.5736 0.1596 0.0694 1.0000 Uiso H313 H 0.5076 0.5078 0.0827 0.0694 1.0000 Uiso H321 H 0.4249 -0.0847 0.1943 0.0573 1.0000 Uiso H322 H 0.3439 -0.0521 0.2175 0.0573 1.0000 Uiso H323 H 0.3400 -0.1241 0.1417 0.0573 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.02424(19) 0.02474(18) 0.0625(3) 0.00665(18) 0.00290(16) -0.00580(15) Cl1 0.0562(5) 0.0265(4) 0.0531(5) 0.0077(4) 0.0235(4) 0.0034(4) Cl2 0.0235(4) 0.0509(5) 0.0458(5) -0.0017(4) 0.0054(3) -0.0074(4) N1 0.0210(12) 0.0245(12) 0.0216(12) -0.0039(10) 0.0088(10) -0.0048(9) C1 0.0155(12) 0.0191(12) 0.0262(15) -0.0010(11) 0.0060(11) -0.0007(10) C2 0.0193(13) 0.0202(13) 0.0250(15) -0.0002(11) 0.0064(11) -0.0001(10) C3 0.0193(13) 0.0243(14) 0.0254(15) 0.0027(12) 0.0076(11) 0.0016(10) C4 0.0197(13) 0.0227(13) 0.0267(15) 0.0052(12) 0.0075(11) 0.0027(11) C5 0.0143(12) 0.0187(12) 0.0304(16) 0.0028(11) 0.0029(11) -0.0015(10) C6 0.0185(13) 0.0185(12) 0.0263(15) -0.0007(12) 0.0040(11) 0.0015(10) C7 0.0181(12) 0.0200(13) 0.0261(15) -0.0016(11) 0.0036(11) -0.0005(10) C8 0.0220(14) 0.0245(14) 0.0269(15) -0.0016(12) 0.0022(12) -0.0020(11) C9 0.0240(14) 0.0325(16) 0.0264(16) -0.0041(13) 0.0009(12) -0.0006(12) C10 0.0307(16) 0.0388(17) 0.0209(15) -0.0015(13) 0.0074(12) -0.0011(13) C11 0.0212(13) 0.0304(14) 0.0255(15) 0.0012(13) 0.0083(11) -0.0007(12) C12 0.0182(12) 0.0248(13) 0.0225(14) 0.0006(12) 0.0030(10) -0.0005(11) C13 0.0181(13) 0.0208(13) 0.0232(14) -0.0019(11) 0.0084(11) -0.0011(10) C14 0.0229(14) 0.0201(13) 0.0278(15) -0.0002(12) 0.0103(12) 0.0005(11) C15 0.0235(14) 0.0266(15) 0.0282(15) -0.0020(13) 0.0056(12) 0.0015(11) C16 0.0270(15) 0.0228(14) 0.0300(16) -0.0042(13) 0.0050(12) -0.0043(12) C17 0.0304(15) 0.0181(13) 0.0374(17) -0.0028(13) 0.0060(13) -0.0012(12) C18 0.0244(14) 0.0222(14) 0.0223(15) 0.0016(11) 0.0044(11) 0.0011(11) C19 0.0271(15) 0.0213(14) 0.0452(19) 0.0004(13) 0.0081(14) 0.0035(11) C20 0.0342(18) 0.0311(18) 0.054(2) -0.0110(17) -0.0051(16) -0.0031(14) C21 0.0298(16) 0.0289(16) 0.0383(18) 0.0026(14) 0.0023(14) 0.0077(13) C22 0.0231(14) 0.0332(16) 0.0331(17) 0.0039(14) 0.0121(13) -0.0031(12) C23 0.0372(18) 0.0443(19) 0.0286(18) -0.0100(15) 0.0046(14) -0.0042(15) C24 0.0259(15) 0.0334(16) 0.0218(15) -0.0019(13) 0.0107(12) -0.0017(12) C25 0.0281(15) 0.0342(16) 0.0294(16) 0.0001(14) 0.0120(12) -0.0002(13) C26 0.0379(18) 0.0348(17) 0.0352(18) 0.0009(15) 0.0162(15) -0.0070(14) C27 0.0296(16) 0.0408(18) 0.0385(18) -0.0044(16) 0.0159(14) -0.0106(15) C28 0.0211(15) 0.0413(18) 0.0378(19) -0.0023(15) 0.0085(13) 0.0002(13) C29 0.0244(14) 0.0315(16) 0.0386(18) -0.0013(15) 0.0112(13) -0.0013(13) C30 0.0343(17) 0.0428(19) 0.042(2) 0.0110(17) 0.0097(15) 0.0065(15) C31 0.035(2) 0.065(3) 0.074(3) 0.006(2) 0.018(2) -0.019(2) C32 0.0342(18) 0.0351(19) 0.074(3) 0.011(2) 0.0067(19) 0.0030(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2558(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ga1 . Cl1 . 2.1269(9) yes Ga1 . Cl2 . 2.1123(9) yes Ga1 . N1 . 1.852(2) yes N1 . C1 . 1.409(4) yes N1 . C12 . 1.394(4) yes C1 . C2 . 1.394(4) yes C1 . C6 . 1.414(4) yes C2 . C3 . 1.409(4) yes C2 . C13 . 1.492(4) yes C3 . C4 . 1.400(4) yes C3 . H31 . 1.000 no C4 . C5 . 1.392(4) yes C4 . C22 . 1.509(4) yes C5 . C6 . 1.393(4) yes C5 . H51 . 1.000 no C6 . C7 . 1.446(4) yes C7 . C8 . 1.394(4) yes C7 . C12 . 1.413(4) yes C8 . C9 . 1.386(5) yes C8 . H81 . 1.000 no C9 . C10 . 1.404(4) yes C9 . C23 . 1.512(5) yes C10 . C11 . 1.395(4) yes C10 . H101 . 1.000 no C11 . C12 . 1.393(4) yes C11 . C24 . 1.492(4) yes C13 . C14 . 1.404(4) yes C13 . C18 . 1.403(4) yes C14 . C15 . 1.386(4) yes C14 . C19 . 1.508(4) yes C15 . C16 . 1.396(4) yes C15 . H151 . 1.000 no C16 . C17 . 1.387(4) yes C16 . C20 . 1.505(4) yes C17 . C18 . 1.395(4) yes C17 . H171 . 1.000 no C18 . C21 . 1.516(4) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . C25 . 1.404(5) yes C24 . C29 . 1.412(5) yes C25 . C26 . 1.403(5) yes C25 . C30 . 1.513(5) yes C26 . C27 . 1.380(5) yes C26 . H261 . 1.000 no C27 . C28 . 1.394(5) yes C27 . C31 . 1.507(5) yes C28 . C29 . 1.387(4) yes C28 . H281 . 1.000 no C29 . C32 . 1.507(5) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no C30 . H303 . 1.000 no C31 . H311 . 1.000 no C31 . H312 . 1.000 no C31 . H313 . 1.000 no C32 . H321 . 1.000 no C32 . H322 . 1.000 no C32 . H323 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . Ga1 . Cl2 . 113.28(4) yes Cl1 . Ga1 . N1 . 120.36(8) yes Cl2 . Ga1 . N1 . 124.75(8) yes Ga1 . N1 . C1 . 129.69(19) yes Ga1 . N1 . C12 . 122.29(19) yes C1 . N1 . C12 . 106.1(2) yes N1 . C1 . C2 . 128.1(3) yes N1 . C1 . C6 . 110.2(2) yes C2 . C1 . C6 . 121.7(3) yes C1 . C2 . C3 . 116.4(3) yes C1 . C2 . C13 . 121.4(2) yes C3 . C2 . C13 . 122.0(3) yes C2 . C3 . C4 . 122.9(3) yes C2 . C3 . H31 . 118.552 no C4 . C3 . H31 . 118.552 no C3 . C4 . C5 . 119.3(3) yes C3 . C4 . C22 . 121.0(3) yes C5 . C4 . C22 . 119.7(3) yes C4 . C5 . C6 . 119.6(3) yes C4 . C5 . H51 . 120.205 no C6 . C5 . H51 . 120.205 no C1 . C6 . C5 . 120.2(3) yes C1 . C6 . C7 . 106.6(2) yes C5 . C6 . C7 . 133.2(3) yes C6 . C7 . C8 . 134.3(3) yes C6 . C7 . C12 . 106.0(2) yes C8 . C7 . C12 . 119.7(3) yes C7 . C8 . C9 . 119.6(3) yes C7 . C8 . H81 . 120.192 no C9 . C8 . H81 . 120.193 no C8 . C9 . C10 . 119.8(3) yes C8 . C9 . C23 . 120.1(3) yes C10 . C9 . C23 . 120.1(3) yes C9 . C10 . C11 . 122.1(3) yes C9 . C10 . H101 . 118.937 no C11 . C10 . H101 . 118.937 no C10 . C11 . C12 . 117.1(3) yes C10 . C11 . C24 . 123.4(3) yes C12 . C11 . C24 . 119.5(3) yes C7 . C12 . N1 . 111.1(2) yes C7 . C12 . C11 . 121.7(3) yes N1 . C12 . C11 . 127.2(3) yes C2 . C13 . C14 . 118.8(3) yes C2 . C13 . C18 . 121.2(3) yes C14 . C13 . C18 . 119.9(3) yes C13 . C14 . C15 . 119.8(3) yes C13 . C14 . C19 . 120.7(3) yes C15 . C14 . C19 . 119.5(3) yes C14 . C15 . C16 . 121.2(3) yes C14 . C15 . H151 . 119.422 no C16 . C15 . H151 . 119.422 no C15 . C16 . C17 . 118.4(3) yes C15 . C16 . C20 . 120.5(3) yes C17 . C16 . C20 . 121.1(3) yes C16 . C17 . C18 . 122.1(3) yes C16 . C17 . H171 . 118.932 no C18 . C17 . H171 . 118.932 no C13 . C18 . C17 . 118.6(3) yes C13 . C18 . C21 . 121.2(3) yes C17 . C18 . C21 . 120.2(3) yes C14 . C19 . H191 . 109.467 no C14 . C19 . H192 . 109.466 no H191 . C19 . H192 . 109.475 no C14 . C19 . H193 . 109.467 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no C16 . C20 . H201 . 109.466 no C16 . C20 . H202 . 109.467 no H201 . C20 . H202 . 109.476 no C16 . C20 . H203 . 109.466 no H201 . C20 . H203 . 109.475 no H202 . C20 . H203 . 109.477 no C18 . C21 . H211 . 109.467 no C18 . C21 . H212 . 109.467 no H211 . C21 . H212 . 109.476 no C18 . C21 . H213 . 109.467 no H211 . C21 . H213 . 109.476 no H212 . C21 . H213 . 109.476 no C4 . C22 . H221 . 109.467 no C4 . C22 . H222 . 109.467 no H221 . C22 . H222 . 109.476 no C4 . C22 . H223 . 109.467 no H221 . C22 . H223 . 109.476 no H222 . C22 . H223 . 109.476 no C9 . C23 . H231 . 109.467 no C9 . C23 . H232 . 109.467 no H231 . C23 . H232 . 109.476 no C9 . C23 . H233 . 109.466 no H231 . C23 . H233 . 109.476 no H232 . C23 . H233 . 109.476 no C11 . C24 . C25 . 120.6(3) yes C11 . C24 . C29 . 119.0(3) yes C25 . C24 . C29 . 120.3(3) yes C24 . C25 . C26 . 118.4(3) yes C24 . C25 . C30 . 121.2(3) yes C26 . C25 . C30 . 120.2(3) yes C25 . C26 . C27 . 121.9(3) yes C25 . C26 . H261 . 119.057 no C27 . C26 . H261 . 119.058 no C26 . C27 . C28 . 118.7(3) yes C26 . C27 . C31 . 120.4(4) yes C28 . C27 . C31 . 120.9(3) yes C27 . C28 . C29 . 121.7(3) yes C27 . C28 . H281 . 119.155 no C29 . C28 . H281 . 119.155 no C24 . C29 . C28 . 118.9(3) yes C24 . C29 . C32 . 120.5(3) yes C28 . C29 . C32 . 120.6(3) yes C25 . C30 . H301 . 109.467 no C25 . C30 . H302 . 109.467 no H301 . C30 . H302 . 109.476 no C25 . C30 . H303 . 109.466 no H301 . C30 . H303 . 109.476 no H302 . C30 . H303 . 109.476 no C27 . C31 . H311 . 109.466 no C27 . C31 . H312 . 109.467 no H311 . C31 . H312 . 109.476 no C27 . C31 . H313 . 109.467 no H311 . C31 . H313 . 109.475 no H312 . C31 . H313 . 109.477 no C29 . C32 . H321 . 109.466 no C29 . C32 . H322 . 109.466 no H321 . C32 . H322 . 109.476 no C29 . C32 . H323 . 109.467 no H321 . C32 . H323 . 109.476 no H322 . C32 . H323 . 109.476 no