# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Hirao, Toshikazu' _publ_contact_author_email hirao@ap.chem.eng.osaka-u.ac.jp _publ_section_title ; Synthesis of (Arylimido)vanadium Complexes and their Application for Oxidative Coupling Reaction of Silyl Enol Ether Derivatives ; loop_ _publ_author_name M.Nishina T.Moriuchi T.Hirao data_vanadium_complex_1b _database_code_depnum_ccdc_archive 'CCDC 774799' #TrackingRef 'MoriuchiCIF.txt' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C8 H10 Cl2 N O V ' _chemical_formula_moiety 'C8 H10 Cl2 N O V ' _chemical_formula_weight 258.02 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,+Z 3 +X,1/2-Y,1/2+Z 4 1/2-X,-Y,1/2+Z 5 -X,-Y,-Z 6 1/2+X,1/2-Y,-Z 7 -X,1/2+Y,1/2-Z 8 1/2+X,+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 11.6418(14) _cell_length_b 7.8118(8) _cell_length_c 24.194(3) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 2200.2(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 12585 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040.00 _exptl_absorpt_coefficient_mu 1.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_T_max 0.851 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.00 _diffrn_reflns_number 19050 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_ambient_temperature 173 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2503 _reflns_number_gt 2218 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0781 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2503 _refine_ls_number_parameters 119 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.8069P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 0.52 _refine_diff_density_min -0.28 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; V V 0.300 0.529 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 V(1) V 0.43288(3) 0.54226(4) 0.556627(11) 0.02164(11) Uani 1.00 1 d . . . Cl(1) Cl 0.52184(4) 0.77715(6) 0.586389(19) 0.03478(13) Uani 1.00 1 d . . . Cl(2) Cl 0.25152(4) 0.57914(7) 0.53162(2) 0.03543(14) Uani 1.00 1 d . . . O(1) O 0.51984(10) 0.37195(15) 0.52703(5) 0.0229(2) Uani 1.00 1 d . . . N(1) N 0.40745(14) 0.46012(19) 0.61850(6) 0.0271(3) Uani 1.00 1 d . . . C(1) C 0.38428(16) 0.4105(2) 0.67214(7) 0.0258(3) Uani 1.00 1 d . . . C(2) C 0.28075(17) 0.3279(2) 0.68445(8) 0.0337(4) Uani 1.00 1 d . . . C(3) C 0.25738(17) 0.2854(2) 0.73909(9) 0.0389(4) Uani 1.00 1 d . . . C(4) C 0.33503(18) 0.3229(2) 0.78028(8) 0.0373(4) Uani 1.00 1 d . . . C(5) C 0.43825(18) 0.4038(2) 0.76786(8) 0.0362(4) Uani 1.00 1 d . . . C(6) C 0.46389(17) 0.4470(2) 0.71384(8) 0.0310(4) Uani 1.00 1 d . . . C(7) C 0.55040(16) 0.2074(2) 0.55178(8) 0.0271(3) Uani 1.00 1 d . . . C(8) C 0.64420(17) 0.2273(2) 0.59432(8) 0.0355(4) Uani 1.00 1 d . . . H(1) H 0.2274 0.3014 0.6560 0.040 Uiso 1.00 1 c R . . H(2) H 0.1872 0.2300 0.7481 0.047 Uiso 1.00 1 c R . . H(3) H 0.3179 0.2933 0.8175 0.045 Uiso 1.00 1 c R . . H(4) H 0.4913 0.4294 0.7965 0.043 Uiso 1.00 1 c R . . H(5) H 0.5348 0.5009 0.7051 0.037 Uiso 1.00 1 c R . . H(6) H 0.5765 0.1281 0.5224 0.032 Uiso 1.00 1 c R . . H(7) H 0.4816 0.1569 0.5695 0.032 Uiso 1.00 1 c R . . H(8) H 0.6627 0.1152 0.6101 0.043 Uiso 1.00 1 c R . . H(9) H 0.6180 0.3042 0.6237 0.043 Uiso 1.00 1 c R . . H(10) H 0.7128 0.2755 0.5767 0.043 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 V(1) 0.02157(17) 0.02407(17) 0.01928(17) 0.00082(11) 0.00173(11) -0.00030(11) Cl(1) 0.0432(2) 0.0326(2) 0.0285(2) -0.00734(19) -0.00624(19) -0.00428(19) Cl(2) 0.0207(2) 0.0431(2) 0.0425(2) 0.00023(17) 0.00129(19) 0.0041(2) O(1) 0.0240(6) 0.0237(5) 0.0209(5) 0.0026(4) 0.0001(4) 0.0012(4) N(1) 0.0283(8) 0.0284(7) 0.0247(7) 0.0009(5) 0.0034(6) -0.0003(6) C(1) 0.0292(9) 0.0253(8) 0.0229(8) 0.0018(6) 0.0049(6) 0.0020(7) C(2) 0.0328(10) 0.0386(10) 0.0297(9) -0.0065(7) -0.0004(7) 0.0002(8) C(3) 0.0342(11) 0.0449(12) 0.0376(10) -0.0081(8) 0.0092(8) 0.0086(9) C(4) 0.0410(11) 0.0445(11) 0.0263(9) 0.0064(9) 0.0080(8) 0.0103(8) C(5) 0.0356(11) 0.0481(11) 0.0250(9) 0.0048(8) -0.0035(7) -0.0004(8) C(6) 0.0269(9) 0.0371(10) 0.0289(9) -0.0020(7) 0.0023(7) 0.0014(8) C(7) 0.0299(9) 0.0219(8) 0.0294(9) 0.0029(6) -0.0030(7) 0.0039(7) C(8) 0.0328(10) 0.0403(10) 0.0333(9) 0.0044(8) -0.0067(8) 0.0069(8) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 V(1) Cl(1) 2.2266(5) yes . . V(1) Cl(2) 2.2151(5) yes . . V(1) O(1) 1.8187(12) yes . . V(1) O(1) 2.2019(12) yes . 5_666 V(1) N(1) 1.6554(14) yes . . O(1) C(7) 1.462(2) yes . . N(1) C(1) 1.381(2) yes . . C(1) C(2) 1.399(2) yes . . C(1) C(6) 1.399(2) yes . . C(2) C(3) 1.390(2) yes . . C(3) C(4) 1.377(2) yes . . C(4) C(5) 1.390(2) yes . . C(5) C(6) 1.382(2) yes . . C(7) C(8) 1.509(2) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(5) H(4) 0.950 no . . C(6) H(5) 0.950 no . . C(7) H(6) 0.990 no . . C(7) H(7) 0.990 no . . C(8) H(8) 0.980 no . . C(8) H(9) 0.980 no . . C(8) H(10) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Cl(1) V(1) Cl(2) 115.12(2) yes . . . Cl(1) V(1) O(1) 118.12(4) yes . . . Cl(1) V(1) O(1) 86.00(3) yes . . 5_666 Cl(1) V(1) N(1) 96.33(5) yes . . . Cl(2) V(1) O(1) 121.21(4) yes . . . Cl(2) V(1) O(1) 87.00(3) yes . . 5_666 Cl(2) V(1) N(1) 97.29(5) yes . . . O(1) V(1) O(1) 73.84(4) yes . . 5_666 O(1) V(1) N(1) 99.91(6) yes . . . O(1) V(1) N(1) 173.66(6) yes 5_666 . . V(1) O(1) V(1) 106.16(5) yes . . 5_666 V(1) O(1) C(7) 128.12(10) yes . . . V(1) O(1) C(7) 125.68(10) yes 5_666 . . V(1) N(1) C(1) 173.46(13) yes . . . N(1) C(1) C(2) 119.85(16) yes . . . N(1) C(1) C(6) 119.41(16) yes . . . C(2) C(1) C(6) 120.73(16) yes . . . C(1) C(2) C(3) 118.77(17) yes . . . C(2) C(3) C(4) 120.60(18) yes . . . C(3) C(4) C(5) 120.51(18) yes . . . C(4) C(5) C(6) 120.12(18) yes . . . C(1) C(6) C(5) 119.26(18) yes . . . O(1) C(7) C(8) 111.42(14) yes . . . C(1) C(2) H(1) 120.6 no . . . C(3) C(2) H(1) 120.6 no . . . C(2) C(3) H(2) 119.7 no . . . C(4) C(3) H(2) 119.7 no . . . C(3) C(4) H(3) 119.7 no . . . C(5) C(4) H(3) 119.8 no . . . C(4) C(5) H(4) 119.9 no . . . C(6) C(5) H(4) 119.9 no . . . C(1) C(6) H(5) 120.4 no . . . C(5) C(6) H(5) 120.4 no . . . O(1) C(7) H(6) 109.3 no . . . O(1) C(7) H(7) 109.3 no . . . C(8) C(7) H(6) 109.3 no . . . C(8) C(7) H(7) 109.4 no . . . H(6) C(7) H(7) 108.0 no . . . C(7) C(8) H(8) 109.5 no . . . C(7) C(8) H(9) 109.5 no . . . C(7) C(8) H(10) 109.5 no . . . H(8) C(8) H(9) 109.5 no . . . H(8) C(8) H(10) 109.5 no . . . H(9) C(8) H(10) 109.5 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Cl(1) V(1) O(1) V(1) -76.27(5) ? . . . 5_666 Cl(1) V(1) O(1) C(7) 105.71(12) ? . . . . Cl(1) V(1) O(1) V(1) 120.81(5) ? . . 5_666 5_666 Cl(1) V(1) O(1) C(7) -57.27(11) ? . . 5_666 5_666 Cl(1) V(1) N(1) C(1) 36.2(12) ? . . . . Cl(2) V(1) O(1) V(1) 76.15(5) ? . . . 5_666 Cl(2) V(1) O(1) C(7) -101.86(12) ? . . . . Cl(2) V(1) O(1) V(1) -123.74(5) ? . . 5_666 5_666 Cl(2) V(1) O(1) C(7) 58.18(12) ? . . 5_666 5_666 Cl(2) V(1) N(1) C(1) -80.2(12) ? . . . . O(1) V(1) O(1) C(7) -178.08(13) ? . . 5_666 5_666 O(1) V(1) O(1) C(7) -178.01(13) ? 5_666 . . . O(1) V(1) N(1) C(1) 156.2(12) ? . . . . N(1) V(1) O(1) V(1) -178.99(6) ? . . . 5_666 N(1) V(1) O(1) C(7) 3.00(14) ? . . . . O(1) V(1) N(1) C(1) 147.4(10) ? 5_666 . . . N(1) V(1) O(1) V(1) 9.1(6) ? . . 5_666 5_666 N(1) V(1) O(1) C(7) -169.0(5) ? . . 5_666 5_666 V(1) O(1) C(7) C(8) -76.87(17) ? . . . . V(1) O(1) C(7) C(8) 105.48(15) ? 5_666 . . . V(1) N(1) C(1) C(2) 108.2(12) ? . . . . V(1) N(1) C(1) C(6) -70.4(13) ? . . . . N(1) C(1) C(2) C(3) -177.45(17) ? . . . . N(1) C(1) C(6) C(5) 177.24(17) ? . . . . C(2) C(1) C(6) C(5) -1.4(2) ? . . . . C(6) C(1) C(2) C(3) 1.1(2) ? . . . . C(1) C(2) C(3) C(4) -0.4(3) ? . . . . C(2) C(3) C(4) C(5) -0.1(2) ? . . . . C(3) C(4) C(5) C(6) -0.1(2) ? . . . . C(4) C(5) C(6) C(1) 0.8(3) ? . . . . data_vanadium_complex_1c _database_code_depnum_ccdc_archive 'CCDC 774800' #TrackingRef 'MoriuchiCIF.txt' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C8 H9 Br Cl2 N O V ' _chemical_formula_moiety 'C8 H9 Br Cl2 N O V ' _chemical_formula_weight 336.92 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,+Z #------------------------------------------------------------------------------ _cell_length_a 7.6595(10) _cell_length_b 11.7903(14) _cell_length_c 13.1806(19) _cell_angle_alpha 90.0000 _cell_angle_beta 101.426(4) _cell_angle_gamma 90.0000 _cell_volume 1166.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7045 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 123.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656.00 _exptl_absorpt_coefficient_mu 4.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.205 _exptl_absorpt_correction_T_max 0.624 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.00 _diffrn_reflns_number 10953 _diffrn_reflns_av_R_equivalents 0.085 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_ambient_temperature 123 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2644 _reflns_number_gt 2222 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1275 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2644 _refine_ls_number_parameters 128 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.7199P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 2.62 _refine_diff_density_min -0.73 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.290 2.459 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; V V 0.300 0.529 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Br(1) Br 1.00769(5) 0.33602(3) 0.60731(3) 0.02664(15) Uani 1.00 1 d . . . V(1) V 0.49751(8) 0.06712(5) 0.10608(5) 0.01849(18) Uani 1.00 1 d . . . Cl(1) Cl 0.29859(12) -0.03342(8) 0.17017(8) 0.0237(2) Uani 1.00 1 d . . . Cl(2) Cl 0.41760(13) 0.24265(7) 0.05536(8) 0.0262(2) Uani 1.00 1 d . . . O(1) O 0.6510(3) -0.0159(2) 0.0478(2) 0.0198(5) Uani 1.00 1 d . . . N(1) N 0.6287(4) 0.1059(2) 0.2166(2) 0.0207(6) Uani 1.00 1 d . . . C(1) C 0.7224(5) 0.1569(3) 0.3044(3) 0.0204(8) Uani 1.00 1 d . . . C(2) C 0.7378(5) 0.2754(3) 0.3073(3) 0.0236(8) Uani 1.00 1 d . . . C(3) C 0.8250(5) 0.3284(3) 0.3968(3) 0.0240(8) Uani 1.00 1 d . . . C(4) C 0.8954(5) 0.2638(3) 0.4829(3) 0.0221(8) Uani 1.00 1 d . . . C(5) C 0.8834(5) 0.1460(3) 0.4812(3) 0.0264(8) Uani 1.00 1 d . . . C(6) C 0.7958(5) 0.0922(3) 0.3916(3) 0.0245(8) Uani 1.00 1 d . . . C(7) C 0.8352(4) -0.0463(3) 0.0925(3) 0.0211(8) Uani 1.00 1 d . . . C(8) C 0.8459(5) -0.1343(3) 0.1759(3) 0.0263(8) Uani 1.00 1 d . . . H(1) H 0.6887 0.3191 0.2480 0.028 Uiso 1.00 1 c R . . H(2) H 0.8364 0.4087 0.3991 0.029 Uiso 1.00 1 c R . . H(3) H 0.9344 0.1029 0.5406 0.032 Uiso 1.00 1 c R . . H(4) H 0.7859 0.0118 0.3896 0.029 Uiso 1.00 1 c R . . H(5) H 0.9004 0.0224 0.1219 0.025 Uiso 1.00 1 c R . . H(6) H 0.8935 -0.0758 0.0373 0.025 Uiso 1.00 1 c R . . H(7) H 0.9711 -0.1522 0.2040 0.032 Uiso 1.00 1 c R . . H(8) H 0.7837 -0.2031 0.1468 0.032 Uiso 1.00 1 c R . . H(9) H 0.7900 -0.1050 0.2314 0.032 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0305(2) 0.0272(2) 0.0220(2) -0.00180(14) 0.00457(18) -0.00459(15) V(1) 0.0181(3) 0.0164(3) 0.0220(4) 0.0002(2) 0.0063(2) -0.0012(2) Cl(1) 0.0239(4) 0.0232(4) 0.0250(5) -0.0027(3) 0.0076(3) 0.0021(3) Cl(2) 0.0295(5) 0.0159(4) 0.0330(6) 0.0008(3) 0.0059(4) -0.0008(3) O(1) 0.0162(12) 0.0195(12) 0.0241(15) 0.0015(9) 0.0049(10) 0.0003(10) N(1) 0.0180(15) 0.0212(16) 0.0245(18) 0.0003(11) 0.0085(13) -0.0011(13) C(1) 0.0162(18) 0.024(2) 0.023(2) -0.0018(13) 0.0088(15) -0.0019(15) C(2) 0.024(2) 0.0241(19) 0.025(2) -0.0005(14) 0.0093(16) 0.0031(15) C(3) 0.026(2) 0.0226(19) 0.025(2) -0.0030(14) 0.0093(16) -0.0033(15) C(4) 0.022(2) 0.0276(19) 0.018(2) -0.0034(14) 0.0063(15) -0.0049(15) C(5) 0.025(2) 0.025(2) 0.029(2) 0.0019(15) 0.0061(17) 0.0004(16) C(6) 0.026(2) 0.0157(17) 0.032(2) -0.0005(14) 0.0059(17) -0.0009(15) C(7) 0.0108(17) 0.0243(18) 0.029(2) 0.0010(13) 0.0058(14) 0.0027(15) C(8) 0.023(2) 0.0247(19) 0.031(2) 0.0042(15) 0.0050(16) 0.0029(17) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br(1) C(4) 1.896(3) yes . . V(1) Cl(1) 2.2249(12) yes . . V(1) Cl(2) 2.2232(10) yes . . V(1) O(1) 1.814(2) yes . . V(1) O(1) 2.203(2) yes . 3_655 V(1) N(1) 1.661(3) yes . . O(1) C(7) 1.462(4) yes . . C(1) C(2) 1.401(5) yes . . C(1) C(6) 1.402(5) yes . . C(2) C(3) 1.385(5) yes . . C(3) C(4) 1.385(5) yes . . C(4) C(5) 1.392(5) yes . . C(5) C(6) 1.390(5) yes . . C(7) C(8) 1.501(5) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(5) H(3) 0.950 no . . C(6) H(4) 0.950 no . . C(7) H(5) 0.990 no . . C(7) H(6) 0.990 no . . C(8) H(7) 0.980 no . . C(8) H(8) 0.980 no . . C(8) H(9) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Cl(1) V(1) Cl(2) 116.21(4) yes . . . Cl(1) V(1) O(1) 115.05(8) yes . . . Cl(1) V(1) O(1) 86.33(7) yes . . 3_655 Cl(1) V(1) N(1) 98.89(12) yes . . . Cl(2) V(1) O(1) 122.55(9) yes . . . Cl(2) V(1) O(1) 85.25(7) yes . . 3_655 Cl(2) V(1) N(1) 95.17(10) yes . . . O(1) V(1) O(1) 73.84(10) yes . . 3_655 O(1) V(1) N(1) 100.95(13) yes . . . O(1) V(1) N(1) 173.90(14) yes 3_655 . . V(1) O(1) V(1) 106.16(11) yes . . 3_655 V(1) O(1) C(7) 128.0(2) yes . . . V(1) O(1) C(7) 125.8(2) yes 3_655 . . V(1) N(1) C(1) 169.5(2) yes . . . N(1) C(1) C(2) 119.1(3) yes . . . N(1) C(1) C(6) 120.7(3) yes . . . C(2) C(1) C(6) 120.2(3) yes . . . C(1) C(2) C(3) 119.8(3) yes . . . C(2) C(3) C(4) 119.6(3) yes . . . Br(1) C(4) C(3) 119.9(2) yes . . . Br(1) C(4) C(5) 118.6(2) yes . . . C(3) C(4) C(5) 121.5(3) yes . . . C(4) C(5) C(6) 119.3(3) yes . . . C(1) C(6) C(5) 119.7(3) yes . . . O(1) C(7) C(8) 111.9(3) yes . . . C(1) C(2) H(1) 120.1 no . . . C(3) C(2) H(1) 120.1 no . . . C(2) C(3) H(2) 120.2 no . . . C(4) C(3) H(2) 120.2 no . . . C(4) C(5) H(3) 120.4 no . . . C(6) C(5) H(3) 120.4 no . . . C(1) C(6) H(4) 120.2 no . . . C(5) C(6) H(4) 120.1 no . . . O(1) C(7) H(5) 109.2 no . . . O(1) C(7) H(6) 109.2 no . . . C(8) C(7) H(5) 109.2 no . . . C(8) C(7) H(6) 109.2 no . . . H(5) C(7) H(6) 107.9 no . . . C(7) C(8) H(7) 109.5 no . . . C(7) C(8) H(8) 109.5 no . . . C(7) C(8) H(9) 109.5 no . . . H(7) C(8) H(8) 109.5 no . . . H(7) C(8) H(9) 109.5 no . . . H(8) C(8) H(9) 109.5 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Cl(1) V(1) O(1) V(1) 77.94(11) ? . . . 3_655 Cl(1) V(1) O(1) C(7) -100.8(2) ? . . . . Cl(1) V(1) O(1) V(1) -117.41(11) ? . . 3_655 3_655 Cl(1) V(1) O(1) C(7) 63.8(2) ? . . 3_655 3_655 Cl(1) V(1) N(1) C(1) -104.2(17) ? . . . . Cl(2) V(1) O(1) V(1) -73.30(12) ? . . . 3_655 Cl(2) V(1) O(1) C(7) 107.9(2) ? . . . . Cl(2) V(1) O(1) V(1) 125.89(11) ? . . 3_655 3_655 Cl(2) V(1) O(1) C(7) -52.9(2) ? . . 3_655 3_655 Cl(2) V(1) N(1) C(1) 13.4(17) ? . . . . O(1) V(1) O(1) C(7) -178.8(2) ? . . 3_655 3_655 O(1) V(1) O(1) C(7) -178.7(3) ? 3_655 . . . O(1) V(1) N(1) C(1) 138.0(17) ? . . . . N(1) V(1) O(1) V(1) -176.75(13) ? . . . 3_655 N(1) V(1) O(1) C(7) 4.5(3) ? . . . . O(1) V(1) N(1) C(1) 107.1(18) ? 3_655 . . . N(1) V(1) O(1) V(1) 31.6(12) ? . . 3_655 3_655 N(1) V(1) O(1) C(7) -147.1(11) ? . . 3_655 3_655 V(1) O(1) C(7) C(8) 72.4(3) ? . . . . V(1) O(1) C(7) C(8) -106.1(3) ? 3_655 . . . V(1) N(1) C(1) C(2) -22.2(19) ? . . . . V(1) N(1) C(1) C(6) 155.4(15) ? . . . . N(1) C(1) C(2) C(3) 177.1(4) ? . . . . N(1) C(1) C(6) C(5) -177.2(4) ? . . . . C(2) C(1) C(6) C(5) 0.3(6) ? . . . . C(6) C(1) C(2) C(3) -0.4(6) ? . . . . C(1) C(2) C(3) C(4) -0.3(6) ? . . . . C(2) C(3) C(4) Br(1) -177.8(3) ? . . . . C(2) C(3) C(4) C(5) 1.1(6) ? . . . . Br(1) C(4) C(5) C(6) 177.7(3) ? . . . . C(3) C(4) C(5) C(6) -1.2(6) ? . . . . C(4) C(5) C(6) C(1) 0.5(6) ? . . . .