# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1093 data_98152a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 98152a _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C7 H14 Cl2 Ga N' _chemical_formula_weight 252.81 _chemical_melting_point ? _chemical_compound_source 'B. Luo / Prof. W. Gladfelter' 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ga' 'Ga' 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y-1/2, z' _cell_length_a 6.0102(2) _cell_length_b 15.8808(3) _cell_length_c 10.7925(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1030.11(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method ? _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 3.132 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6030 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 24.98 _reflns_number_total 962 _reflns_number_observed 853 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+1.4984P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 962 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_obs 0.0338 _refine_ls_wR_factor_all 0.0840 _refine_ls_wR_factor_obs 0.0802 _refine_ls_goodness_of_fit_all 1.152 _refine_ls_goodness_of_fit_obs 1.172 _refine_ls_restrained_S_all 1.152 _refine_ls_restrained_S_obs 1.172 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ga1 Ga 0.65812(9) 0.58354(3) 0.7500 0.0346(2) Uani 1 d S . H1 H 0.3851(81) 0.5987(33) 0.7500 0.042 Uiso 1 d S . Cl1 Cl 0.8324(2) 0.62991(6) 0.91401(8) 0.0524(3) Uani 1 d . . N1 N 0.7269(6) 0.4592(2) 0.7500 0.0234(7) Uani 1 d S . C1 C 0.6238(6) 0.4198(2) 0.8629(3) 0.0365(8) Uani 1 d . . H1A H 0.4619(6) 0.4314(2) 0.8634(3) 0.044 Uiso 1 calc R . H1B H 0.6890(6) 0.4453(2) 0.9383(3) 0.044 Uiso 1 calc R . C2 C 0.6624(6) 0.3247(2) 0.8650(4) 0.0436(9) Uani 1 d . . H2A H 0.7472(6) 0.3090(2) 0.9402(4) 0.052 Uiso 1 calc R . H2B H 0.5178(6) 0.2949(2) 0.8671(4) 0.052 Uiso 1 calc R . C3 C 0.7916(8) 0.2989(3) 0.7500 0.0391(12) Uani 1 d S . H3A H 0.8169(8) 0.2366(3) 0.7500 0.047 Uiso 1 calc SR . C4 C 1.0144(8) 0.3454(3) 0.7500 0.0347(10) Uani 1 d S . H4A H 1.0987(8) 0.3301(3) 0.8221 0.042 Uiso 1 d R . C5 C 0.9704(7) 0.4408(3) 0.7500 0.0355(11) Uani 1 d S . H5A H 1.0376(7) 0.4656(3) 0.8220 0.043 Uiso 1 d 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 Ga1 0.0394(3) 0.0219(3) 0.0426(3) 0.000 0.000 -0.0003(2) Cl1 0.0855(8) 0.0402(5) 0.0316(5) -0.0105(4) 0.0071(5) -0.0183(5) N1 0.024(2) 0.023(2) 0.023(2) 0.000 0.000 -0.0018(14) C1 0.043(2) 0.032(2) 0.035(2) 0.0043(15) 0.013(2) -0.0028(15) C2 0.038(2) 0.031(2) 0.061(2) 0.017(2) 0.006(2) -0.003(2) C3 0.034(3) 0.022(2) 0.062(3) 0.000 0.000 0.003(2) C4 0.026(2) 0.035(2) 0.043(3) 0.000 0.000 0.007(2) C5 0.024(2) 0.033(2) 0.050(3) 0.000 0.000 -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 Ga1 N1 2.017(3) . ? Ga1 Cl1 2.1846(10) . ? Ga1 Cl1 2.1847(10) 6_557 ? Ga1 H1 1.66(5) . ? N1 C5 1.493(6) . ? N1 C1 1.503(4) 6_557 ? N1 C1 1.504(4) . ? C1 C2 1.529(5) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.520(5) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C2 1.520(5) 6_557 ? C3 C4 1.529(6) . ? C3 H3A 1.00 . ? C4 C5 1.537(6) . ? C4 H4A 0.96 . ? C5 H5A 0.96 . ? 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 Ga1 Cl1 103.40(6) . . ? N1 Ga1 Cl1 103.40(6) . 6_557 ? Cl1 Ga1 Cl1 108.24(6) . 6_557 ? N1 Ga1 H1 110.2(18) . . ? Cl1 Ga1 H1 115.2(8) . . ? Cl1 Ga1 H1 115.2(8) 6_557 . ? C5 N1 C1 108.8(2) . 6_557 ? C5 N1 C1 108.8(2) . . ? C1 N1 C1 108.3(3) 6_557 . ? C5 N1 Ga1 113.2(3) . . ? C1 N1 Ga1 108.8(2) 6_557 . ? C1 N1 Ga1 108.9(2) . . ? N1 C1 C2 111.1(3) . . ? N1 C1 H1A 109.4(2) . . ? C2 C1 H1A 109.4(2) . . ? N1 C1 H1B 109.4(2) . . ? C2 C1 H1B 109.4(2) . . ? H1A C1 H1B 108.0 . . ? C3 C2 C1 109.4(3) . . ? C3 C2 H2A 109.8(2) . . ? C1 C2 H2A 109.8(2) . . ? C3 C2 H2B 109.8(2) . . ? C1 C2 H2B 109.8(2) . . ? H2A C2 H2B 108.2 . . ? C2 C3 C2 109.4(4) 6_557 . ? C2 C3 C4 108.5(3) 6_557 . ? C2 C3 C4 108.5(3) . . ? C2 C3 H3A 110.1(2) 6_557 . ? C2 C3 H3A 110.1(2) . . ? C4 C3 H3A 110.1(2) . . ? C3 C4 C5 109.0(4) . . ? C3 C4 H4A 109.88(12) . . ? C5 C4 H4A 109.88(12) . . ? N1 C5 C4 111.2(4) . . ? N1 C5 H5A 109.39(11) . . ? C4 C5 H5A 109.38(12) . . ? 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 Cl1 Ga1 N1 C5 -56.40(4) . . . . ? Cl1 Ga1 N1 C5 56.40(4) 6_557 . . . ? Cl1 Ga1 N1 C1 -177.5(2) . . . 6_557 ? Cl1 Ga1 N1 C1 -64.7(2) 6_557 . . 6_557 ? Cl1 Ga1 N1 C1 64.7(2) . . . . ? Cl1 Ga1 N1 C1 177.5(2) 6_557 . . . ? C5 N1 C1 C2 -58.6(4) . . . . ? C1 N1 C1 C2 59.5(4) 6_557 . . . ? Ga1 N1 C1 C2 177.6(2) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C2 -58.3(5) . . . 6_557 ? C1 C2 C3 C4 59.8(4) . . . . ? C2 C3 C4 C5 59.4(3) 6_557 . . . ? C2 C3 C4 C5 -59.4(3) . . . . ? C1 N1 C5 C4 -58.9(2) 6_557 . . . ? C1 N1 C5 C4 58.9(2) . . . . ? Ga1 N1 C5 C4 180.0 . . . . ? C3 C4 C5 N1 0.0 . . . . ? _refine_diff_density_max 1.149 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.082 #=END data_98154 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 98154 _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H28 Cl Ga N2' _chemical_formula_weight 329.56 _chemical_melting_point ? _chemical_compound_source 'B. Luo / Prof. W. Gladfelter' 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ga' 'Ga' 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.9098(2) _cell_length_b 12.0848(2) _cell_length_c 12.3099(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1622.97(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method ? _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.847 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8527 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1433 _reflns_number_observed 1202 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+1.1045P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1433 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_obs 0.0296 _refine_ls_wR_factor_all 0.0644 _refine_ls_wR_factor_obs 0.0606 _refine_ls_goodness_of_fit_all 1.117 _refine_ls_goodness_of_fit_obs 1.154 _refine_ls_restrained_S_all 1.117 _refine_ls_restrained_S_obs 1.154 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ga1 Ga 0.0000 0.38828(3) 0.2500 0.02603(13) Uani 1 d S . H1 H 0.0730(21) 0.4440(19) 0.1618(19) 0.037(6) Uiso 1 d . . Cl1 Cl 0.0000 0.20083(6) 0.2500 0.0312(2) Uani 1 d S . N1 N 0.1657(2) 0.39113(14) 0.35994(14) 0.0247(4) Uani 1 d . . C1 C 0.1377(2) 0.3410(2) 0.4677(2) 0.0332(5) Uani 1 d . . H1A H 0.1076(2) 0.2645(2) 0.4571(2) 0.040 Uiso 1 calc R . H1B H 0.0718(2) 0.3840(2) 0.5034(2) 0.040 Uiso 1 calc R . C2 C 0.2512(2) 0.3389(2) 0.5418(2) 0.0404(6) Uani 1 d . . H2A H 0.2303(2) 0.3698(2) 0.6140(2) 0.048 Uiso 1 calc R . H2B H 0.2795(2) 0.2618(2) 0.5518(2) 0.048 Uiso 1 calc R . C3 C 0.1977(2) 0.5089(2) 0.3778(2) 0.0350(6) Uani 1 d . . H3A H 0.1239(2) 0.5494(2) 0.4026(2) 0.042 Uiso 1 calc R . H3B H 0.2247(2) 0.5420(2) 0.3083(2) 0.042 Uiso 1 calc R . C4 C 0.3000(2) 0.5220(2) 0.4628(2) 0.0389(6) Uani 1 d . . H4A H 0.3654(2) 0.5706(2) 0.4340(2) 0.047 Uiso 1 calc R . H4B H 0.2667(2) 0.5563(2) 0.5296(2) 0.047 Uiso 1 calc R . C5 C 0.2744(2) 0.3346(2) 0.3128(2) 0.0339(6) Uani 1 d . . H5A H 0.2889(2) 0.3629(2) 0.2385(2) 0.041 Uiso 1 calc R . H5B H 0.2578(2) 0.2543(2) 0.3076(2) 0.041 Uiso 1 calc R . C6 C 0.3900(2) 0.3534(2) 0.3822(2) 0.0453(7) Uani 1 d . . H6A H 0.4308(2) 0.2818(2) 0.3970(2) 0.054 Uiso 1 calc R . H6B H 0.4484(2) 0.4015(2) 0.3427(2) 0.054 Uiso 1 calc R . C7 C 0.3525(2) 0.4081(2) 0.4889(2) 0.0358(6) Uani 1 d . . H7A H 0.4246(2) 0.4148(2) 0.5387(2) 0.043 Uiso 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 Ga1 0.0259(2) 0.0268(2) 0.0255(2) 0.000 -0.0012(2) 0.000 Cl1 0.0371(4) 0.0270(4) 0.0296(4) 0.000 -0.0037(4) 0.000 N1 0.0262(10) 0.0247(9) 0.0231(9) 0.0023(7) -0.0004(8) -0.0005(8) C1 0.0357(14) 0.0381(13) 0.0258(12) 0.0052(11) -0.0013(11) -0.0082(11) C2 0.050(2) 0.0414(14) 0.0301(13) 0.0080(11) -0.0116(12) -0.0092(13) C3 0.0349(13) 0.0263(12) 0.0436(15) 0.0007(11) -0.0063(12) -0.0037(11) C4 0.0385(15) 0.0355(13) 0.0426(14) 0.0000(11) -0.0073(12) -0.0120(11) C5 0.0294(13) 0.0428(13) 0.0293(13) -0.0045(11) -0.0003(11) 0.0073(11) C6 0.0317(14) 0.060(2) 0.045(2) -0.0044(14) -0.0059(13) 0.0087(13) C7 0.0318(14) 0.0428(14) 0.0329(13) 0.0040(11) -0.0111(11) -0.0047(11) _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 Ga1 N1 2.259(2) 3 ? Ga1 N1 2.259(2) . ? Ga1 Cl1 2.2653(8) . ? Ga1 H1 1.51(2) . ? N1 C3 1.482(3) . ? N1 C5 1.486(3) . ? N1 C1 1.490(3) . ? C1 C2 1.537(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C7 1.531(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.538(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C7 1.525(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.541(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.526(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 H7A 1.00 . ? 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 Ga1 N1 178.25(9) 3 . ? N1 Ga1 Cl1 90.88(4) 3 . ? N1 Ga1 Cl1 90.88(4) . . ? N1 Ga1 H1 89.1(9) 3 . ? N1 Ga1 H1 90.1(9) . . ? Cl1 Ga1 H1 116.6(9) . . ? C3 N1 C5 108.2(2) . . ? C3 N1 C1 107.8(2) . . ? C5 N1 C1 108.9(2) . . ? C3 N1 Ga1 106.98(13) . . ? C5 N1 Ga1 113.43(13) . . ? C1 N1 Ga1 111.29(13) . . ? N1 C1 C2 111.7(2) . . ? N1 C1 H1A 109.28(11) . . ? C2 C1 H1A 109.28(13) . . ? N1 C1 H1B 109.28(12) . . ? C2 C1 H1B 109.28(14) . . ? H1A C1 H1B 107.9 . . ? C7 C2 C1 108.7(2) . . ? C7 C2 H2A 109.95(13) . . ? C1 C2 H2A 109.95(14) . . ? C7 C2 H2B 109.95(14) . . ? C1 C2 H2B 109.95(13) . . ? H2A C2 H2B 108.3 . . ? N1 C3 C4 111.8(2) . . ? N1 C3 H3A 109.27(12) . . ? C4 C3 H3A 109.27(13) . . ? N1 C3 H3B 109.27(12) . . ? C4 C3 H3B 109.27(13) . . ? H3A C3 H3B 107.9 . . ? C7 C4 C3 108.9(2) . . ? C7 C4 H4A 109.91(14) . . ? C3 C4 H4A 109.91(13) . . ? C7 C4 H4B 109.91(14) . . ? C3 C4 H4B 109.91(13) . . ? H4A C4 H4B 108.3 . . ? N1 C5 C6 111.7(2) . . ? N1 C5 H5A 109.29(12) . . ? C6 C5 H5A 109.29(14) . . ? N1 C5 H5B 109.29(12) . . ? C6 C5 H5B 109.29(15) . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 108.7(2) . . ? C7 C6 H6A 109.94(14) . . ? C5 C6 H6A 109.94(14) . . ? C7 C6 H6B 109.94(15) . . ? C5 C6 H6B 109.94(14) . . ? H6A C6 H6B 108.3 . . ? C4 C7 C6 108.0(2) . . ? C4 C7 C2 108.1(2) . . ? C6 C7 C2 108.8(2) . . ? C4 C7 H7A 110.58(13) . . ? C6 C7 H7A 110.58(13) . . ? C2 C7 H7A 110.58(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ga1 N1 C3 -1.31(13) 3 . . . ? Cl1 Ga1 N1 C3 178.69(13) . . . . ? N1 Ga1 N1 C5 -120.50(14) 3 . . . ? Cl1 Ga1 N1 C5 59.50(14) . . . . ? N1 Ga1 N1 C1 116.26(14) 3 . . . ? Cl1 Ga1 N1 C1 -63.74(14) . . . . ? C3 N1 C1 C2 -64.9(2) . . . . ? C5 N1 C1 C2 52.3(2) . . . . ? Ga1 N1 C1 C2 178.0(2) . . . . ? N1 C1 C2 C7 10.0(3) . . . . ? C5 N1 C3 C4 -64.3(2) . . . . ? C1 N1 C3 C4 53.3(2) . . . . ? Ga1 N1 C3 C4 173.1(2) . . . . ? N1 C3 C4 C7 9.4(3) . . . . ? C3 N1 C5 C6 53.0(3) . . . . ? C1 N1 C5 C6 -64.0(3) . . . . ? Ga1 N1 C5 C6 171.5(2) . . . . ? N1 C5 C6 C7 9.7(3) . . . . ? C3 C4 C7 C6 53.5(3) . . . . ? C3 C4 C7 C2 -64.1(2) . . . . ? C5 C6 C7 C4 -64.3(3) . . . . ? C5 C6 C7 C2 52.9(3) . . . . ? C1 C2 C7 C4 53.0(3) . . . . ? C1 C2 C7 C6 -64.1(3) . . . . ? _refine_diff_density_max 0.205 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.047 #=END data_98215b _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 98215b _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H23 Cl2 Ga N2' _chemical_formula_weight 359.96 _chemical_melting_point ? _chemical_compound_source 'B. Lou / Prof. W. Gladfelter' 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ga' 'Ga' 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmn2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y, z+1/2' '-x, y, z' _cell_length_a 10.2217(6) _cell_length_b 12.2916(7) _cell_length_c 6.4620(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 811.89(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method ? _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.013 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4661 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.08 _reflns_number_total 1458 _reflns_number_observed 1321 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+1.4665P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(4) _refine_ls_number_reflns 1457 _refine_ls_number_parameters 102 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_obs 0.0529 _refine_ls_wR_factor_all 0.1491 _refine_ls_wR_factor_obs 0.1365 _refine_ls_goodness_of_fit_all 1.099 _refine_ls_goodness_of_fit_obs 1.111 _refine_ls_restrained_S_all 1.151 _refine_ls_restrained_S_obs 1.110 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ga1 Ga 0.0000 0.30081(7) 0.49304(13) 0.0214(3) Uani 1 d SD . H1 H 0.0000 0.3526(16) 0.2749(31) 0.032 Uiso 1 d SD . Cl1 Cl -0.1833(2) 0.2589(2) 0.6674(4) 0.0542(6) Uani 1 d D . N1 N 0.0000 0.4699(6) 0.6278(13) 0.022(2) Uani 1 d SD . C1 C 0.0000 0.4753(8) 0.8565(17) 0.032(3) Uani 1 d S . H1B H -0.0760 0.4381(8) 0.9078(17) 0.038 Uiso 0.50 d PR . C2 C 0.0000 0.5933(9) 0.9355(15) 0.035(3) Uani 1 d S . H2B H -0.0763 0.6062(9) 1.0184(15) 0.042 Uiso 0.50 d PR . C3 C 0.0000 0.6697(8) 0.7523(19) 0.034(3) Uani 1 d S . H3A H 0.0000 0.7473(8) 0.7989(19) 0.041 Uiso 1 calc SR . C4 C -0.1173(6) 0.5259(5) 0.5510(11) 0.028(2) Uani 1 d . . H4A H -0.1963(6) 0.4878(5) 0.6018(11) 0.033 Uiso 1 calc R . H4B H -0.1183(6) 0.5235(5) 0.3979(11) 0.033 Uiso 1 calc R . C5 C -0.1204(9) 0.6450(7) 0.6236(13) 0.041(2) Uani 1 d . . H5A H -0.1231(9) 0.6939(7) 0.5020(13) 0.050 Uiso 1 calc R . H5B H -0.2001(9) 0.6580(7) 0.7071(13) 0.050 Uiso 1 calc R . N2 N 0.0000 0.1369(6) 0.3442(13) 0.022(2) Uani 1 d SD . C6 C 0.0000 0.0447(7) 0.4995(23) 0.028(2) Uani 1 d S . H6A H -0.0762 0.0498(7) 0.5857(23) 0.033 Uiso 0.50 d PR . C7 C 0.0000 -0.0661(9) 0.3897(23) 0.050(3) Uani 1 d S . H7A H -0.0761 -0.1072(9) 0.4286(23) 0.060 Uiso 0.50 d PR . C8 C 0.0000 -0.0494(9) 0.1579(20) 0.042(3) Uani 1 d S . H8A H 0.0000 -0.1211(9) 0.0848(20) 0.050 Uiso 1 calc SR . C9 C -0.1179(7) 0.1239(6) 0.2073(12) 0.030(2) Uani 1 d . . H9A H -0.1173(7) 0.1816(6) 0.1005(12) 0.036 Uiso 1 calc R . H9B H -0.1982(7) 0.1330(6) 0.2914(12) 0.036 Uiso 1 calc R . C10 C -0.1209(8) 0.0145(7) 0.1033(14) 0.043(2) Uani 1 d . . H10A H -0.1996(8) -0.0261(7) 0.1480(14) 0.052 Uiso 1 calc R . H10B H -0.1256(8) 0.0242(7) -0.0486(14) 0.052 Uiso 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 Ga1 0.0221(4) 0.0222(5) 0.0199(5) 0.0019(6) 0.000 0.000 Cl1 0.0483(13) 0.0552(14) 0.059(2) -0.0008(12) 0.0118(12) -0.0035(11) N1 0.023(4) 0.027(4) 0.015(5) 0.008(3) 0.000 0.000 C1 0.043(6) 0.025(5) 0.027(7) 0.002(4) 0.000 0.000 C2 0.042(6) 0.041(6) 0.022(8) -0.011(4) 0.000 0.000 C3 0.043(6) 0.022(5) 0.038(7) 0.001(4) 0.000 0.000 C4 0.026(3) 0.034(4) 0.023(5) -0.004(3) -0.007(3) 0.006(3) C5 0.051(5) 0.036(5) 0.036(5) -0.001(3) -0.015(4) 0.012(4) N2 0.021(4) 0.024(4) 0.019(5) 0.005(4) 0.000 0.000 C6 0.037(5) 0.027(4) 0.019(5) -0.005(7) 0.000 0.000 C7 0.062(8) 0.024(6) 0.064(9) 0.002(6) 0.000 0.000 C8 0.063(8) 0.033(6) 0.030(7) -0.011(5) 0.000 0.000 C9 0.020(4) 0.041(4) 0.029(4) 0.000(3) -0.004(3) 0.000(3) C10 0.039(5) 0.055(6) 0.036(5) -0.015(4) -0.006(4) -0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 N2 2.232(8) . ? Ga1 Cl1 2.246(2) 4 ? Ga1 Cl1 2.246(2) . ? Ga1 N1 2.254(8) . ? Ga1 H1 1.55(2) . ? N1 C4 1.469(7) 4 ? N1 C4 1.469(7) . ? N1 C1 1.479(14) . ? C1 C2 1.538(14) . ? C1 H1B 0.96 . ? C2 C3 1.511(15) . ? C2 H2B 0.96 . ? C3 C5 1.516(11) 4 ? C3 C5 1.516(11) . ? C3 H3A 1.00 . ? C4 C5 1.538(10) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? N2 C9 1.504(8) . ? N2 C9 1.504(8) 4 ? N2 C6 1.514(14) . ? C6 C7 1.54(2) . ? C6 H6A 0.96 . ? C7 C8 1.51(2) . ? C7 H7A 0.96 . ? C8 C10 1.506(11) . ? C8 C10 1.506(11) 4 ? C8 H8A 1.00 . ? C9 C10 1.504(10) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ga1 Cl1 90.52(13) . 4 ? N2 Ga1 Cl1 90.52(13) . . ? Cl1 Ga1 Cl1 113.04(15) 4 . ? N2 Ga1 N1 177.2(3) . . ? Cl1 Ga1 N1 91.02(13) 4 . ? Cl1 Ga1 N1 91.02(13) . . ? N2 Ga1 H1 88.8(7) . . ? Cl1 Ga1 H1 123.48(7) 4 . ? Cl1 Ga1 H1 123.48(7) . . ? N1 Ga1 H1 88.4(7) . . ? C4 N1 C4 109.5(7) 4 . ? C4 N1 C1 108.5(5) 4 . ? C4 N1 C1 108.5(5) . . ? C4 N1 Ga1 107.5(4) 4 . ? C4 N1 Ga1 107.5(4) . . ? C1 N1 Ga1 115.3(6) . . ? N1 C1 C2 111.9(8) . . ? N1 C1 H1B 108.9(3) . . ? C2 C1 H1B 109.5(3) . . ? C3 C2 C1 109.0(8) . . ? C3 C2 H2B 109.6(3) . . ? C1 C2 H2B 110.0(3) . . ? C2 C3 C5 107.8(6) . 4 ? C2 C3 C5 107.8(6) . . ? C5 C3 C5 108.5(10) 4 . ? C2 C3 H3A 110.9(5) . . ? C5 C3 H3A 110.9(5) 4 . ? C5 C3 H3A 110.9(5) . . ? N1 C4 C5 111.1(6) . . ? N1 C4 H4A 109.4(4) . . ? C5 C4 H4A 109.4(4) . . ? N1 C4 H4B 109.4(4) . . ? C5 C4 H4B 109.4(4) . . ? H4A C4 H4B 108.0 . . ? C3 C5 C4 110.0(7) . . ? C3 C5 H5A 109.7(5) . . ? C4 C5 H5A 109.7(4) . . ? C3 C5 H5B 109.7(5) . . ? C4 C5 H5B 109.7(4) . . ? H5A C5 H5B 108.2 . . ? C9 N2 C9 106.6(7) . 4 ? C9 N2 C6 108.1(5) . . ? C9 N2 C6 108.1(5) 4 . ? C9 N2 Ga1 110.4(4) . . ? C9 N2 Ga1 110.4(4) 4 . ? C6 N2 Ga1 113.0(7) . . ? N2 C6 C7 111.0(11) . . ? N2 C6 H6A 109.6(3) . . ? C7 C6 H6A 109.1(4) . . ? C8 C7 C6 109.7(10) . . ? C8 C7 H7A 109.3(3) . . ? C6 C7 H7A 110.2(4) . . ? C10 C8 C10 110.2(10) . 4 ? C10 C8 C7 107.7(7) . . ? C10 C8 C7 107.7(7) 4 . ? C10 C8 H8A 110.4(5) . . ? C10 C8 H8A 110.4(5) 4 . ? C7 C8 H8A 110.4(6) . . ? N2 C9 C10 112.0(6) . . ? N2 C9 H9A 109.2(4) . . ? C10 C9 H9A 109.2(5) . . ? N2 C9 H9B 109.2(4) . . ? C10 C9 H9B 109.2(4) . . ? H9A C9 H9B 107.9 . . ? C8 C10 C9 110.2(7) . . ? C8 C10 H10A 109.6(5) . . ? C9 C10 H10A 109.6(4) . . ? C8 C10 H10B 109.6(6) . . ? C9 C10 H10B 109.6(5) . . ? H10A C10 H10B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ga1 N1 C4 -58.9(4) . . . 4 ? Cl1 Ga1 N1 C4 64.6(4) 4 . . 4 ? Cl1 Ga1 N1 C4 177.6(4) . . . 4 ? N2 Ga1 N1 C4 58.9(4) . . . . ? Cl1 Ga1 N1 C4 -177.6(4) 4 . . . ? Cl1 Ga1 N1 C4 -64.6(4) . . . . ? N2 Ga1 N1 C1 180.00(3) . . . . ? Cl1 Ga1 N1 C1 -56.53(7) 4 . . . ? Cl1 Ga1 N1 C1 56.53(7) . . . . ? C4 N1 C1 C2 59.4(5) 4 . . . ? C4 N1 C1 C2 -59.4(5) . . . . ? Ga1 N1 C1 C2 180.000(3) . . . . ? N1 C1 C2 C3 0.000(5) . . . . ? C1 C2 C3 C5 -58.5(6) . . . 4 ? C1 C2 C3 C5 58.5(6) . . . . ? C4 N1 C4 C5 -59.6(9) 4 . . . ? C1 N1 C4 C5 58.6(8) . . . . ? Ga1 N1 C4 C5 -176.1(5) . . . . ? C2 C3 C5 C4 -59.3(9) . . . . ? C5 C3 C5 C4 57.1(11) 4 . . . ? N1 C4 C5 C3 0.5(9) . . . . ? Cl1 Ga1 N2 C9 177.7(4) 4 . . . ? Cl1 Ga1 N2 C9 64.7(5) . . . . ? N1 Ga1 N2 C9 -58.8(4) . . . . ? Cl1 Ga1 N2 C9 -64.7(5) 4 . . 4 ? Cl1 Ga1 N2 C9 -177.7(4) . . . 4 ? N1 Ga1 N2 C9 58.8(4) . . . 4 ? Cl1 Ga1 N2 C6 56.52(7) 4 . . . ? Cl1 Ga1 N2 C6 -56.52(7) . . . . ? N1 Ga1 N2 C6 180.000(10) . . . . ? C9 N2 C6 C7 57.5(5) . . . . ? C9 N2 C6 C7 -57.5(5) 4 . . . ? Ga1 N2 C6 C7 180.000(1) . . . . ? N2 C6 C7 C8 0.000(1) . . . . ? C6 C7 C8 C10 -59.4(6) . . . . ? C6 C7 C8 C10 59.4(6) . . . 4 ? C9 N2 C9 C10 59.7(9) 4 . . . ? C6 N2 C9 C10 -56.3(8) . . . . ? Ga1 N2 C9 C10 179.7(5) . . . . ? C10 C8 C10 C9 -55.6(12) 4 . . . ? C7 C8 C10 C9 61.5(9) . . . . ? N2 C9 C10 C8 -2.9(10) . . . . ? _refine_diff_density_max 0.680 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.141