Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_name 'Prof Hubert Schmidbaur' _publ_contact_author_address ; Anorganische und Analytische Chemie Technische Universitaet Muenchen Lichtenbergstr. 4 Garching D-85747 GERMANY ; _publ_contact_author_phone '++49 89 2891-3130' _publ_contact_author_fax '++49 89 2891-3125' _publ_contact_author_email H.Schmidbaur@lrz.tu-muenchen.de _publ_requested_coeditor_name ? _publ_contact_letter ? #=========================================================================== #========================================================================== #== # 2. PROCESSING SUMMARY _journal_coden_Cambridge 0222 _journal_name_full 'Dalton Trans.' _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #=========================================================================== #========================================================================== #== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Reactions of Trichlorogermane HGeCl3 and Dichlorogallane HGaCl2 with Pyridine Donors ; loop_ _publ_author_name _publ_author_address 'H. Schmidbaur' ; Anorganisch-chemisches Institut der Technischen Universit\"at M\"unchen Lichtenbergstra\"se 4 D-85747 Garching Germany ; 'S. Nogai' ; Anorganisch-chemisches Institut der Technischen Universit\"at M\"unchen Lichtenbergstra\"se 4 D-85747 Garching Germany ; 'A. Schriewer' ; Anorganisch-chemisches Institut der Technischen Universit\"at M\"unchen Lichtenbergstra\"se 4 D-85747 Garching Germany ; #=========================================================================== #========================================================================== #========20 data_alex1 _database_code_CSD 211295 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H6 Cl3 Ge N' _chemical_formula_weight 259.05 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' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8187(2) _cell_length_b 9.3672(2) _cell_length_c 11.3129(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.4859(19) _cell_angle_gamma 90.00 _cell_volume 915.80(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 21681 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 4.147 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.555 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21681 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 25.44 _reflns_number_total 1614 _reflns_number_gt 1607 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All C - H hydrogens were calculated in ideal positions and refined after a riding model, the N - H hydrogen was located and refined with isotropic displacement parameters. ; _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^)+(0.0198P)^2^+3.0188P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1614 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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 Ge1 Ge 0.77045(5) 0.22515(4) 0.72622(4) 0.02465(15) Uani 1 1 d . . . Cl1 Cl 0.95709(10) 0.40037(11) 0.75227(9) 0.0288(2) Uani 1 1 d . . . Cl2 Cl 0.56700(10) 0.38705(11) 0.69390(9) 0.0295(2) Uani 1 1 d . . . Cl3 Cl 0.76977(11) 0.19433(10) 0.93004(9) 0.0275(2) Uani 1 1 d . . . N1 N 1.2666(4) 0.3623(4) 0.4508(3) 0.0274(7) Uani 1 1 d . . . C6 C 1.3510(5) 0.2708(4) 0.4032(4) 0.0293(9) Uani 1 1 d . . . H6A H 1.4114 0.3026 0.3475 0.035 Uiso 1 1 calc R . . C3 C 1.1770(4) 0.1863(4) 0.5646(4) 0.0284(9) Uani 1 1 d . . . H3A H 1.1156 0.1579 0.6207 0.034 Uiso 1 1 calc R . . C2 C 1.1806(4) 0.3258(4) 0.5312(4) 0.0283(9) Uani 1 1 d . . . H2A H 1.1233 0.3959 0.5643 0.034 Uiso 1 1 calc R . . C4 C 1.2628(5) 0.0862(4) 0.5166(4) 0.0315(9) Uani 1 1 d . . . H4A H 1.2610 -0.0112 0.5396 0.038 Uiso 1 1 calc R . . C5 C 1.3511(5) 0.1286(4) 0.4349(4) 0.0303(9) Uani 1 1 d . . . H5A H 1.4108 0.0611 0.4011 0.036 Uiso 1 1 calc R . . H1 H 1.277(6) 0.446(6) 0.433(5) 0.048(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ge1 0.0301(3) 0.0207(2) 0.0238(3) -0.00246(15) 0.00688(17) 0.00007(16) Cl1 0.0217(5) 0.0339(5) 0.0318(6) 0.0000(4) 0.0081(4) -0.0025(4) Cl2 0.0207(4) 0.0349(5) 0.0326(6) 0.0083(4) 0.0046(4) 0.0006(4) Cl3 0.0336(5) 0.0240(4) 0.0255(5) 0.0042(4) 0.0076(4) 0.0010(4) N1 0.0227(16) 0.0237(17) 0.036(2) 0.0081(15) 0.0068(14) 0.0024(13) C6 0.0235(19) 0.032(2) 0.033(2) 0.0010(17) 0.0079(17) -0.0030(16) C3 0.0264(19) 0.029(2) 0.031(2) 0.0024(17) 0.0094(16) -0.0050(16) C2 0.0228(19) 0.027(2) 0.036(2) -0.0022(17) 0.0098(16) 0.0029(16) C4 0.036(2) 0.0196(18) 0.038(3) 0.0031(17) 0.0037(18) -0.0021(16) C5 0.026(2) 0.029(2) 0.036(3) -0.0055(17) 0.0082(17) 0.0049(16) _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 Ge1 Cl1 2.3014(10) . ? Ge1 Cl2 2.3219(10) . ? Ge1 Cl3 2.3249(11) . ? N1 C6 1.319(5) . ? N1 C2 1.339(5) . ? N1 H1 0.82(5) . ? C6 C5 1.379(6) . ? C6 H6A 0.9500 . ? C3 C2 1.363(6) . ? C3 C4 1.382(6) . ? C3 H3A 0.9500 . ? C2 H2A 0.9500 . ? C4 C5 1.380(6) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ge1 Cl2 93.72(4) . . ? Cl1 Ge1 Cl3 96.00(4) . . ? Cl2 Ge1 Cl3 94.75(4) . . ? C6 N1 C2 123.6(4) . . ? C6 N1 H1 115(4) . . ? C2 N1 H1 121(4) . . ? N1 C6 C5 119.5(4) . . ? N1 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? N1 C2 C3 118.8(4) . . ? N1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C6 C5 C4 118.7(4) . . ? C6 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C6 C5 1.1(6) . . . . ? C6 N1 C2 C3 -1.4(6) . . . . ? C4 C3 C2 N1 0.9(6) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? N1 C6 C5 C4 -0.4(6) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl2 0.82(5) 2.69(5) 3.362(4) 141(5) 3_766 N1 H1 Cl3 0.82(5) 2.87(5) 3.430(4) 128(4) 2_756 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.565 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.097 #======END data_nog31 _database_code_CSD 211296 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H6 Cl2 Ga N' _chemical_formula_weight 220.73 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9436(2) _cell_length_b 8.5157(2) _cell_length_c 13.4892(4) _cell_angle_alpha 86.5446(11) _cell_angle_beta 74.6191(13) _cell_angle_gamma 65.1942(15) _cell_volume 797.27(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 20638 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 4.032 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.6370 _exptl_absorpt_correction_T_max 0.8930 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20638 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2738 _reflns_number_gt 2681 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0261P)^2^+0.5820P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2738 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 Ga1 Ga -0.39039(3) 1.03153(3) 0.347901(19) 0.02345(9) Uani 1 1 d . . . Cl1 Cl -0.47602(9) 1.29988(7) 0.39967(5) 0.03208(15) Uani 1 1 d . . . Cl2 Cl -0.34162(9) 1.02218(8) 0.18038(4) 0.03491(15) Uani 1 1 d . . . H1 H -0.512(4) 0.951(4) 0.406(2) 0.042(8) Uiso 1 1 d . . . Ga2 Ga 0.11149(4) 0.38288(3) 0.226170(19) 0.02630(9) Uani 1 1 d . . . Cl3 Cl 0.13014(11) 0.23353(9) 0.09400(5) 0.04058(17) Uani 1 1 d . . . Cl4 Cl -0.19029(9) 0.56076(8) 0.28686(5) 0.03788(16) Uani 1 1 d . . . H2 H 0.198(4) 0.292(3) 0.3089(19) 0.024(6) Uiso 1 1 d . . . N11 N -0.1253(3) 0.9177(2) 0.36785(15) 0.0237(4) Uani 1 1 d . . . C12 C 0.0126(3) 0.9621(3) 0.31144(19) 0.0265(5) Uani 1 1 d . . . H12 H -0.021(4) 1.044(3) 0.266(2) 0.024(6) Uiso 1 1 d . . . C13 C 0.1960(4) 0.8896(3) 0.3236(2) 0.0289(5) Uani 1 1 d . . . H13 H 0.285(5) 0.926(4) 0.282(2) 0.038(8) Uiso 1 1 d . . . C14 C 0.2387(4) 0.7673(3) 0.3963(2) 0.0307(5) Uani 1 1 d . . . H14 H 0.360(5) 0.715(4) 0.409(2) 0.040(8) Uiso 1 1 d . . . C15 C 0.0966(4) 0.7221(3) 0.4546(2) 0.0309(5) Uani 1 1 d . . . H15 H 0.115(4) 0.648(4) 0.499(2) 0.029(7) Uiso 1 1 d . . . C16 C -0.0845(4) 0.7989(3) 0.43893(18) 0.0268(5) Uani 1 1 d . . . H16 H -0.182(4) 0.772(4) 0.473(2) 0.033(7) Uiso 1 1 d . . . N21 N 0.2323(3) 0.5394(2) 0.15839(14) 0.0241(4) Uani 1 1 d . . . C22 C 0.1404(4) 0.6680(3) 0.10255(19) 0.0285(5) Uani 1 1 d . . . H22 H 0.020(4) 0.675(4) 0.101(2) 0.035(7) Uiso 1 1 d . . . C23 C 0.2212(4) 0.7734(3) 0.0514(2) 0.0322(5) Uani 1 1 d . . . H23 H 0.157(5) 0.853(4) 0.012(3) 0.044(9) Uiso 1 1 d . . . C24 C 0.4022(4) 0.7488(3) 0.0561(2) 0.0314(5) Uani 1 1 d . . . H24 H 0.454(4) 0.819(4) 0.024(2) 0.025(7) Uiso 1 1 d . . . C25 C 0.4973(4) 0.6169(3) 0.1132(2) 0.0307(5) Uani 1 1 d . . . H25 H 0.628(4) 0.590(3) 0.113(2) 0.030(7) Uiso 1 1 d . . . C26 C 0.4086(3) 0.5149(3) 0.16310(19) 0.0275(5) Uani 1 1 d . . . H26 H 0.460(4) 0.425(4) 0.202(2) 0.032(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.02254(14) 0.02573(15) 0.02336(15) 0.00437(10) -0.00920(11) -0.00986(11) Cl1 0.0378(3) 0.0250(3) 0.0346(3) 0.0041(2) -0.0163(3) -0.0106(2) Cl2 0.0363(3) 0.0383(3) 0.0237(3) 0.0038(2) -0.0114(2) -0.0078(3) Ga2 0.03162(16) 0.02539(15) 0.02565(16) 0.00443(11) -0.00944(12) -0.01478(12) Cl3 0.0565(4) 0.0393(3) 0.0350(3) -0.0035(3) -0.0103(3) -0.0289(3) Cl4 0.0299(3) 0.0394(3) 0.0429(4) -0.0006(3) -0.0043(3) -0.0159(3) N11 0.0235(9) 0.0233(9) 0.0246(10) 0.0017(8) -0.0081(8) -0.0091(8) C12 0.0298(12) 0.0261(11) 0.0266(12) 0.0035(10) -0.0109(10) -0.0127(10) C13 0.0276(12) 0.0323(12) 0.0308(13) -0.0022(10) -0.0060(11) -0.0167(11) C14 0.0261(12) 0.0319(12) 0.0335(13) -0.0034(10) -0.0125(11) -0.0081(10) C15 0.0321(13) 0.0296(12) 0.0271(12) 0.0039(10) -0.0134(11) -0.0062(11) C16 0.0271(12) 0.0276(12) 0.0239(11) 0.0040(9) -0.0059(10) -0.0105(10) N21 0.0278(9) 0.0236(9) 0.0223(9) 0.0008(7) -0.0069(8) -0.0118(8) C22 0.0268(12) 0.0294(12) 0.0282(12) 0.0031(10) -0.0088(10) -0.0099(10) C23 0.0334(13) 0.0285(12) 0.0302(13) 0.0069(10) -0.0071(11) -0.0101(11) C24 0.0375(13) 0.0281(12) 0.0287(12) 0.0015(10) -0.0012(11) -0.0182(11) C25 0.0290(12) 0.0363(13) 0.0301(13) -0.0019(10) -0.0084(10) -0.0158(11) C26 0.0315(12) 0.0265(11) 0.0266(12) 0.0028(10) -0.0120(10) -0.0117(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 N11 2.0004(18) . ? Ga1 Cl2 2.1895(6) . ? Ga1 Cl1 2.1928(6) . ? Ga1 H1 1.45(3) . ? Ga2 N21 1.998(2) . ? Ga2 Cl4 2.1847(7) . ? Ga2 Cl3 2.1893(6) . ? Ga2 H2 1.47(3) . ? N11 C12 1.339(3) . ? N11 C16 1.350(3) . ? C12 C13 1.375(3) . ? C12 H12 0.90(3) . ? C13 C14 1.386(4) . ? C13 H13 0.93(3) . ? C14 C15 1.378(4) . ? C14 H14 0.94(3) . ? C15 C16 1.377(3) . ? C15 H15 0.84(3) . ? C16 H16 0.90(3) . ? N21 C26 1.345(3) . ? N21 C22 1.349(3) . ? C22 C23 1.366(4) . ? C22 H22 0.94(3) . ? C23 C24 1.382(4) . ? C23 H23 0.90(3) . ? C24 C25 1.384(4) . ? C24 H24 0.89(3) . ? C25 C26 1.378(4) . ? C25 H25 0.96(3) . ? C26 H26 0.92(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 N11 Ga1 Cl2 103.82(6) . . ? N11 Ga1 Cl1 100.85(6) . . ? Cl2 Ga1 Cl1 107.76(3) . . ? N11 Ga1 H1 111.3(12) . . ? Cl2 Ga1 H1 116.6(12) . . ? Cl1 Ga1 H1 114.8(11) . . ? N21 Ga2 Cl4 103.08(6) . . ? N21 Ga2 Cl3 102.06(6) . . ? Cl4 Ga2 Cl3 107.37(3) . . ? N21 Ga2 H2 111.1(10) . . ? Cl4 Ga2 H2 111.7(10) . . ? Cl3 Ga2 H2 119.9(9) . . ? C12 N11 C16 119.5(2) . . ? C12 N11 Ga1 119.74(16) . . ? C16 N11 Ga1 120.79(16) . . ? N11 C12 C13 121.9(2) . . ? N11 C12 H12 116.9(18) . . ? C13 C12 H12 121.2(18) . . ? C12 C13 C14 118.9(2) . . ? C12 C13 H13 117.5(19) . . ? C14 C13 H13 123.6(19) . . ? C15 C14 C13 119.3(2) . . ? C15 C14 H14 118(2) . . ? C13 C14 H14 123(2) . . ? C16 C15 C14 119.3(2) . . ? C16 C15 H15 118(2) . . ? C14 C15 H15 123(2) . . ? N11 C16 C15 121.3(2) . . ? N11 C16 H16 115.6(18) . . ? C15 C16 H16 123.1(18) . . ? C26 N21 C22 118.6(2) . . ? C26 N21 Ga2 121.38(16) . . ? C22 N21 Ga2 119.96(17) . . ? N21 C22 C23 121.9(2) . . ? N21 C22 H22 113.9(19) . . ? C23 C22 H22 124.2(19) . . ? C22 C23 C24 119.7(2) . . ? C22 C23 H23 118(2) . . ? C24 C23 H23 122(2) . . ? C23 C24 C25 118.7(3) . . ? C23 C24 H24 119.8(17) . . ? C25 C24 H24 121.4(17) . . ? C26 C25 C24 119.0(2) . . ? C26 C25 H25 120.5(17) . . ? C24 C25 H25 120.3(18) . . ? N21 C26 C25 122.1(2) . . ? N21 C26 H26 112.7(18) . . ? C25 C26 H26 125.1(18) . . ? 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 Cl2 Ga1 N11 C12 46.44(17) . . . . ? Cl1 Ga1 N11 C12 -65.09(17) . . . . ? Cl2 Ga1 N11 C16 -134.80(16) . . . . ? Cl1 Ga1 N11 C16 113.66(16) . . . . ? C16 N11 C12 C13 0.1(3) . . . . ? Ga1 N11 C12 C13 178.90(17) . . . . ? N11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C12 N11 C16 C15 0.0(3) . . . . ? Ga1 N11 C16 C15 -178.78(17) . . . . ? C14 C15 C16 N11 -0.2(4) . . . . ? Cl4 Ga2 N21 C26 141.62(16) . . . . ? Cl3 Ga2 N21 C26 -107.09(17) . . . . ? Cl4 Ga2 N21 C22 -41.44(17) . . . . ? Cl3 Ga2 N21 C22 69.85(17) . . . . ? C26 N21 C22 C23 -0.2(3) . . . . ? Ga2 N21 C22 C23 -177.23(18) . . . . ? N21 C22 C23 C24 0.2(4) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C22 N21 C26 C25 0.2(3) . . . . ? Ga2 N21 C26 C25 177.16(17) . . . . ? C24 C25 C26 N21 -0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.395 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.069 #======END data_nog32 _database_code_CSD 211297 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H11 Cl2 Ga N2' _chemical_formula_weight 263.80 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 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 7.31330(10) _cell_length_b 16.9338(3) _cell_length_c 8.5934(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.9279(7) _cell_angle_gamma 90.00 _cell_volume 1056.45(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 22853 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 3.060 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.5610 _exptl_absorpt_correction_T_max 0.8650 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22853 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.44 _reflns_number_total 1833 _reflns_number_gt 1811 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0312P)^2^+0.4095P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1833 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0587 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.003 _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 Ga1 Ga 0.15035(3) 0.801066(11) 0.11319(2) 0.02784(10) Uani 1 1 d . . . Cl1 Cl -0.06569(7) 0.85735(3) -0.05059(6) 0.03895(14) Uani 1 1 d . . . Cl2 Cl 0.40302(7) 0.80823(3) -0.00015(6) 0.03667(14) Uani 1 1 d . . . H1 H 0.102(3) 0.7237(15) 0.172(3) 0.043(6) Uiso 1 1 d . . . N11 N 0.1895(2) 0.87709(9) 0.28767(17) 0.0270(3) Uani 1 1 d . . . C12 C 0.2251(2) 0.85090(12) 0.4370(2) 0.0278(4) Uani 1 1 d . . . H12 H 0.220(3) 0.7975(13) 0.449(2) 0.027(6) Uiso 1 1 d . . . C13 C 0.2581(3) 0.89970(11) 0.5633(2) 0.0283(4) Uani 1 1 d . . . H13 H 0.277(3) 0.8773(13) 0.665(3) 0.031(5) Uiso 1 1 d . . . C14 C 0.2572(2) 0.98289(10) 0.54193(19) 0.0243(3) Uani 1 1 d . . . C15 C 0.2187(3) 1.00963(11) 0.3844(2) 0.0269(4) Uani 1 1 d . . . H15 H 0.210(3) 1.0610(13) 0.360(2) 0.029(5) Uiso 1 1 d . . . C16 C 0.1868(3) 0.95624(11) 0.2655(2) 0.0279(4) Uani 1 1 d . . . H16 H 0.155(3) 0.9707(12) 0.161(3) 0.025(5) Uiso 1 1 d . . . N41 N 0.2896(2) 1.03323(9) 0.66263(16) 0.0270(3) Uani 1 1 d . . . C41 C 0.3359(3) 1.00334(12) 0.8223(2) 0.0345(4) Uani 1 1 d . . . H41C H 0.230(3) 0.9733(14) 0.855(3) 0.038(6) Uiso 1 1 d . . . H41B H 0.435(3) 0.9695(14) 0.823(3) 0.038(6) Uiso 1 1 d . . . H41A H 0.364(3) 1.0494(15) 0.886(2) 0.037(6) Uiso 1 1 d . . . C42 C 0.2840(3) 1.11818(11) 0.6384(2) 0.0316(4) Uani 1 1 d . . . H42C H 0.376(4) 1.1336(15) 0.582(3) 0.050(7) Uiso 1 1 d . . . H42B H 0.174(4) 1.1352(16) 0.580(3) 0.050(7) Uiso 1 1 d . . . H42A H 0.297(4) 1.1445(18) 0.732(4) 0.067(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.02983(17) 0.02682(14) 0.02657(14) -0.00339(7) 0.00211(9) -0.00302(7) Cl1 0.0358(3) 0.0425(3) 0.0359(3) -0.00069(19) -0.00633(19) -0.00060(19) Cl2 0.0352(3) 0.0354(3) 0.0411(3) -0.00580(18) 0.0116(2) -0.00079(17) N11 0.0246(8) 0.0289(7) 0.0273(7) -0.0027(6) 0.0023(6) 0.0004(6) C12 0.0255(10) 0.0255(9) 0.0319(9) 0.0014(7) 0.0021(7) 0.0011(6) C13 0.0285(11) 0.0295(9) 0.0265(9) 0.0034(7) 0.0020(7) 0.0010(7) C14 0.0181(9) 0.0287(9) 0.0263(8) -0.0012(6) 0.0031(6) 0.0004(6) C15 0.0272(10) 0.0252(9) 0.0279(9) 0.0021(7) 0.0017(7) 0.0002(7) C16 0.0271(10) 0.0313(9) 0.0248(9) 0.0015(7) 0.0012(7) -0.0002(7) N41 0.0293(9) 0.0274(7) 0.0239(7) -0.0003(6) 0.0015(6) -0.0006(6) C41 0.0450(13) 0.0335(10) 0.0240(9) 0.0002(8) 0.0005(8) -0.0013(9) C42 0.0349(12) 0.0282(9) 0.0315(9) -0.0025(8) 0.0029(8) -0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 N11 1.9707(15) . ? Ga1 Cl2 2.1937(5) . ? Ga1 Cl1 2.2021(5) . ? Ga1 H1 1.46(3) . ? N11 C12 1.353(2) . ? N11 C16 1.354(2) . ? C12 C13 1.362(3) . ? C12 H12 0.91(2) . ? C13 C14 1.421(3) . ? C13 H13 0.94(2) . ? C14 N41 1.341(2) . ? C14 C15 1.423(2) . ? C15 C16 1.363(3) . ? C15 H15 0.89(2) . ? C16 H16 0.94(2) . ? N41 C42 1.453(2) . ? N41 C41 1.464(2) . ? C41 H41C 1.00(2) . ? C41 H41B 0.92(3) . ? C41 H41A 0.96(2) . ? C42 H42C 0.92(3) . ? C42 H42B 0.94(3) . ? C42 H42A 0.92(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 N11 Ga1 Cl2 104.41(5) . . ? N11 Ga1 Cl1 103.34(5) . . ? Cl2 Ga1 Cl1 105.67(2) . . ? N11 Ga1 H1 109.8(9) . . ? Cl2 Ga1 H1 117.2(9) . . ? Cl1 Ga1 H1 115.1(10) . . ? C12 N11 C16 117.13(15) . . ? C12 N11 Ga1 120.08(12) . . ? C16 N11 Ga1 122.77(12) . . ? N11 C12 C13 123.51(18) . . ? N11 C12 H12 115.5(13) . . ? C13 C12 H12 121.0(13) . . ? C12 C13 C14 120.09(17) . . ? C12 C13 H13 118.9(13) . . ? C14 C13 H13 121.0(13) . . ? N41 C14 C13 122.19(15) . . ? N41 C14 C15 121.99(16) . . ? C13 C14 C15 115.82(15) . . ? C16 C15 C14 119.89(16) . . ? C16 C15 H15 118.0(14) . . ? C14 C15 H15 122.1(13) . . ? N11 C16 C15 123.57(16) . . ? N11 C16 H16 113.2(12) . . ? C15 C16 H16 123.2(12) . . ? C14 N41 C42 121.27(15) . . ? C14 N41 C41 120.30(15) . . ? C42 N41 C41 118.41(15) . . ? N41 C41 H41C 110.1(14) . . ? N41 C41 H41B 108.5(15) . . ? H41C C41 H41B 108(2) . . ? N41 C41 H41A 105.3(13) . . ? H41C C41 H41A 112.0(18) . . ? H41B C41 H41A 112(2) . . ? N41 C42 H42C 110.4(16) . . ? N41 C42 H42B 112.7(16) . . ? H42C C42 H42B 106(2) . . ? N41 C42 H42A 110.9(19) . . ? H42C C42 H42A 109(2) . . ? H42B C42 H42A 108(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ga1 N11 C12 -106.55(13) . . . . ? Cl1 Ga1 N11 C12 143.11(13) . . . . ? Cl2 Ga1 N11 C16 71.89(14) . . . . ? Cl1 Ga1 N11 C16 -38.45(15) . . . . ? C16 N11 C12 C13 -0.2(3) . . . . ? Ga1 N11 C12 C13 178.32(14) . . . . ? N11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 N41 -179.77(17) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? N41 C14 C15 C16 179.92(17) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C12 N11 C16 C15 0.4(3) . . . . ? Ga1 N11 C16 C15 -178.11(14) . . . . ? C14 C15 C16 N11 -0.1(3) . . . . ? C13 C14 N41 C42 -178.66(17) . . . . ? C15 C14 N41 C42 1.0(3) . . . . ? C13 C14 N41 C41 2.8(3) . . . . ? C15 C14 N41 C41 -177.53(18) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.396 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.053 #======END data_nog33 _database_code_CSD 211298 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 Cl2 Ga N2' _chemical_formula_weight 245.74 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4429(7) _cell_length_b 8.3052(3) _cell_length_c 11.0553(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.466(3) _cell_angle_gamma 90.00 _cell_volume 928.43(9) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 11088 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 3.476 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.679 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11088 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.36 _reflns_number_total 1624 _reflns_number_gt 1558 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0271P)^2^+0.4392P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1624 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0617 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Ga1 Ga 0.29213(2) 0.22134(3) 0.43259(2) 0.03289(12) Uani 1 1 d . . . Cl1 Cl 0.22440(6) 0.31129(8) 0.24123(5) 0.04056(16) Uani 1 1 d . . . Cl2 Cl 0.12232(6) 0.12080(8) 0.48587(6) 0.04464(17) Uani 1 1 d . . . N1 N 0.31597(16) 0.4289(2) 0.53050(15) 0.0299(4) Uani 1 1 d . . . C5 C 0.2541(3) 0.6991(3) 0.5572(2) 0.0360(5) Uani 1 1 d . . . C4 C 0.3572(2) 0.7118(3) 0.6636(2) 0.0331(5) Uani 1 1 d . . . C3 C 0.4360(2) 0.5797(3) 0.7049(2) 0.0383(5) Uani 1 1 d . . . C6 C 0.2370(2) 0.5554(3) 0.4936(2) 0.0357(5) Uani 1 1 d . . . C2 C 0.4137(2) 0.4396(3) 0.6369(2) 0.0367(5) Uani 1 1 d . . . C41 C 0.3838(2) 0.8640(3) 0.7297(2) 0.0404(5) Uani 1 1 d . . . N42 N 0.4080(2) 0.9834(3) 0.7806(2) 0.0550(6) Uani 1 1 d . . . H1 H 0.417(2) 0.126(3) 0.468(2) 0.036(6) Uiso 1 1 d . . . H6 H 0.171(2) 0.539(3) 0.424(2) 0.039(7) Uiso 1 1 d . . . H2 H 0.462(3) 0.345(4) 0.661(2) 0.040(6) Uiso 1 1 d . . . H5 H 0.202(3) 0.779(3) 0.533(3) 0.040(7) Uiso 1 1 d . . . H3 H 0.498(3) 0.580(4) 0.772(3) 0.057(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.03271(17) 0.0323(2) 0.03375(17) -0.00119(8) 0.00851(11) -0.00135(8) Cl1 0.0466(3) 0.0457(4) 0.0292(3) -0.0031(2) 0.0091(2) -0.0076(2) Cl2 0.0496(3) 0.0404(4) 0.0483(3) -0.0035(2) 0.0206(3) -0.0141(2) N1 0.0279(8) 0.0328(10) 0.0273(8) 0.0011(7) 0.0038(7) -0.0030(7) C5 0.0409(13) 0.0352(14) 0.0290(11) 0.0027(9) 0.0035(9) 0.0030(10) C4 0.0323(11) 0.0402(15) 0.0286(11) -0.0055(8) 0.0109(9) -0.0098(8) C3 0.0276(10) 0.0532(16) 0.0299(11) -0.0035(10) -0.0009(9) -0.0011(10) C6 0.0359(11) 0.0375(13) 0.0281(11) 0.0025(9) -0.0024(9) -0.0019(9) C2 0.0291(11) 0.0459(15) 0.0319(11) 0.0018(9) 0.0016(9) 0.0048(10) C41 0.0365(12) 0.0500(16) 0.0355(11) -0.0092(11) 0.0107(9) -0.0063(10) N42 0.0519(13) 0.0594(16) 0.0549(13) -0.0219(12) 0.0154(10) -0.0125(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 2.0174(18) . ? Ga1 Cl2 2.1705(6) . ? Ga1 Cl1 2.1878(6) . ? Ga1 H1 1.49(2) . ? N1 C6 1.335(3) . ? N1 C2 1.354(3) . ? C5 C6 1.374(3) . ? C5 C4 1.385(3) . ? C5 H5 0.86(3) . ? C4 C3 1.380(3) . ? C4 C41 1.452(3) . ? C3 C2 1.373(3) . ? C3 H3 0.86(3) . ? C6 H6 0.91(2) . ? C2 H2 0.94(3) . ? C41 N42 1.137(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 Ga1 Cl2 100.53(5) . . ? N1 Ga1 Cl1 101.18(5) . . ? Cl2 Ga1 Cl1 107.77(2) . . ? N1 Ga1 H1 109.2(9) . . ? Cl2 Ga1 H1 116.4(9) . . ? Cl1 Ga1 H1 119.0(9) . . ? C6 N1 C2 119.16(19) . . ? C6 N1 Ga1 121.64(14) . . ? C2 N1 Ga1 119.19(15) . . ? C6 C5 C4 118.3(2) . . ? C6 C5 H5 121.1(19) . . ? C4 C5 H5 120.6(19) . . ? C3 C4 C5 119.6(2) . . ? C3 C4 C41 120.2(2) . . ? C5 C4 C41 120.3(2) . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3 118(2) . . ? C4 C3 H3 123(2) . . ? N1 C6 C5 122.4(2) . . ? N1 C6 H6 114.9(17) . . ? C5 C6 H6 122.7(17) . . ? N1 C2 C3 121.3(2) . . ? N1 C2 H2 115.2(16) . . ? C3 C2 H2 123.5(16) . . ? N42 C41 C4 178.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ga1 N1 C6 -76.57(17) . . . . ? Cl1 Ga1 N1 C6 34.10(17) . . . . ? Cl2 Ga1 N1 C2 102.79(15) . . . . ? Cl1 Ga1 N1 C2 -146.53(15) . . . . ? C6 C5 C4 C3 -2.3(3) . . . . ? C6 C5 C4 C41 176.4(2) . . . . ? C5 C4 C3 C2 2.5(3) . . . . ? C41 C4 C3 C2 -176.3(2) . . . . ? C2 N1 C6 C5 2.5(3) . . . . ? Ga1 N1 C6 C5 -178.13(18) . . . . ? C4 C5 C6 N1 -0.1(4) . . . . ? C6 N1 C2 C3 -2.4(3) . . . . ? Ga1 N1 C2 C3 178.25(17) . . . . ? C4 C3 C2 N1 -0.1(3) . . . . ? C3 C4 C41 N42 64(9) . . . . ? C5 C4 C41 N42 -114(9) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.347 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.060 #======END data_nog37 _database_code_CSD 211299 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 Cl2 Ga N' _chemical_formula_weight 248.78 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 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 8.1301(2) _cell_length_b 9.1466(2) _cell_length_c 13.7748(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.9204(12) _cell_angle_gamma 90.00 _cell_volume 1002.24(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 28989 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 3.218 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_T_max 0.836 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28989 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1830 _reflns_number_gt 1791 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0301P)^2^+0.5653P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1830 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.22973(3) 0.83450(2) 0.897079(16) 0.03221(11) Uani 1 1 d . . . Cl1 Cl 0.29594(7) 0.91723(6) 1.04858(4) 0.04072(15) Uani 1 1 d . . . N1 N 0.0321(2) 0.70508(19) 0.90129(12) 0.0287(4) Uani 1 1 d . . . Cl2 Cl 0.11675(8) 1.01044(7) 0.79818(4) 0.04702(17) Uani 1 1 d . . . C2 C 0.0025(3) 0.5912(2) 0.83754(15) 0.0295(4) Uani 1 1 d . . . H2 H 0.078(3) 0.583(2) 0.7965(16) 0.028(6) Uiso 1 1 d . . . C3 C -0.1281(2) 0.4943(2) 0.83681(15) 0.0300(4) Uani 1 1 d . . . C4 C -0.2307(3) 0.5196(2) 0.90429(16) 0.0314(4) Uani 1 1 d . . . H4 H -0.314(3) 0.459(3) 0.9054(18) 0.038(6) Uiso 1 1 d . . . C5 C -0.2033(3) 0.6364(2) 0.97053(15) 0.0310(4) Uani 1 1 d . . . C6 C -0.0684(3) 0.7273(2) 0.96598(15) 0.0295(4) Uani 1 1 d . . . H6 H -0.041(3) 0.809(3) 1.0086(17) 0.028(6) Uiso 1 1 d . . . C7 C -0.1554(3) 0.3664(3) 0.76725(19) 0.0392(5) Uani 1 1 d . . . H7C H -0.261(5) 0.376(4) 0.720(3) 0.070(9) Uiso 1 1 d . . . H7B H -0.152(5) 0.288(5) 0.797(3) 0.084(12) Uiso 1 1 d . . . H7A H -0.082(5) 0.363(4) 0.731(3) 0.068(10) Uiso 1 1 d . . . C8 C -0.3112(3) 0.6646(3) 1.0446(2) 0.0409(6) Uani 1 1 d . . . H8C H -0.244(5) 0.695(5) 1.102(3) 0.096(15) Uiso 1 1 d . . . H8B H -0.360(6) 0.581(5) 1.065(3) 0.117(15) Uiso 1 1 d . . . H8A H -0.391(6) 0.723(5) 1.022(3) 0.099(14) Uiso 1 1 d . . . H1 H 0.360(3) 0.746(3) 0.8558(17) 0.034(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.03164(17) 0.03385(17) 0.03323(17) -0.00201(9) 0.01154(11) -0.00322(8) Cl1 0.0406(3) 0.0465(3) 0.0348(3) -0.0060(2) 0.0074(2) -0.0060(2) N1 0.0295(8) 0.0282(8) 0.0285(8) 0.0030(7) 0.0059(7) 0.0023(7) Cl2 0.0554(4) 0.0427(3) 0.0419(3) 0.0115(2) 0.0077(3) -0.0080(3) C2 0.0307(10) 0.0315(10) 0.0265(9) 0.0039(8) 0.0065(8) 0.0040(8) C3 0.0305(10) 0.0290(10) 0.0289(10) 0.0044(8) 0.0025(8) 0.0027(8) C4 0.0271(10) 0.0316(11) 0.0339(11) 0.0063(8) 0.0024(8) -0.0005(9) C5 0.0267(10) 0.0333(10) 0.0325(11) 0.0054(9) 0.0054(8) 0.0057(8) C6 0.0302(10) 0.0288(10) 0.0293(10) 0.0011(8) 0.0056(8) 0.0035(8) C7 0.0444(14) 0.0359(12) 0.0377(12) -0.0024(10) 0.0096(11) -0.0050(10) C8 0.0334(12) 0.0467(15) 0.0455(14) -0.0017(11) 0.0151(11) 0.0008(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 N1 2.0059(17) . ? Ga1 Cl1 2.1803(6) . ? Ga1 Cl2 2.1846(6) . ? Ga1 H1 1.53(2) . ? N1 C6 1.343(3) . ? N1 C2 1.352(3) . ? C2 C3 1.382(3) . ? C2 H2 0.92(2) . ? C3 C4 1.391(3) . ? C3 C7 1.499(3) . ? C4 C5 1.393(3) . ? C4 H4 0.88(3) . ? C5 C6 1.388(3) . ? C5 C8 1.499(3) . ? C6 H6 0.95(2) . ? C7 H7C 0.96(4) . ? C7 H7B 0.83(4) . ? C7 H7A 0.86(4) . ? C8 H8C 0.90(4) . ? C8 H8B 0.93(5) . ? C8 H8A 0.84(5) . ? 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 102.59(5) . . ? N1 Ga1 Cl2 102.51(5) . . ? Cl1 Ga1 Cl2 109.28(3) . . ? N1 Ga1 H1 108.6(9) . . ? Cl1 Ga1 H1 119.0(9) . . ? Cl2 Ga1 H1 113.0(9) . . ? C6 N1 C2 119.76(18) . . ? C6 N1 Ga1 122.05(14) . . ? C2 N1 Ga1 118.18(14) . . ? N1 C2 C3 122.19(19) . . ? N1 C2 H2 114.3(14) . . ? C3 C2 H2 123.5(14) . . ? C2 C3 C4 117.04(19) . . ? C2 C3 C7 121.2(2) . . ? C4 C3 C7 121.8(2) . . ? C3 C4 C5 121.9(2) . . ? C3 C4 H4 118.6(16) . . ? C5 C4 H4 119.5(16) . . ? C6 C5 C4 116.80(19) . . ? C6 C5 C8 120.4(2) . . ? C4 C5 C8 122.8(2) . . ? N1 C6 C5 122.30(19) . . ? N1 C6 H6 115.5(14) . . ? C5 C6 H6 122.2(14) . . ? C3 C7 H7C 111(2) . . ? C3 C7 H7B 112(3) . . ? H7C C7 H7B 111(3) . . ? C3 C7 H7A 112(2) . . ? H7C C7 H7A 104(3) . . ? H7B C7 H7A 107(3) . . ? C5 C8 H8C 108(3) . . ? C5 C8 H8B 114(3) . . ? H8C C8 H8B 102(4) . . ? C5 C8 H8A 112(3) . . ? H8C C8 H8A 114(4) . . ? H8B C8 H8A 107(4) . . ? 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 C6 26.63(16) . . . . ? Cl2 Ga1 N1 C6 -86.71(15) . . . . ? Cl1 Ga1 N1 C2 -152.35(13) . . . . ? Cl2 Ga1 N1 C2 94.32(14) . . . . ? C6 N1 C2 C3 -0.6(3) . . . . ? Ga1 N1 C2 C3 178.37(15) . . . . ? N1 C2 C3 C4 0.8(3) . . . . ? N1 C2 C3 C7 -178.3(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C7 C3 C4 C5 178.6(2) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C8 -179.3(2) . . . . ? C2 N1 C6 C5 0.2(3) . . . . ? Ga1 N1 C6 C5 -178.72(15) . . . . ? C4 C5 C6 N1 0.0(3) . . . . ? C8 C5 C6 N1 179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.352 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.065 #======END data_nog39 _database_code_CSD 211300 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 Ga N' _chemical_formula_weight 179.90 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' Ga Ga 0.2307 1.6083 '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 8.9394(3) _cell_length_b 13.8205(5) _cell_length_c 14.0935(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.1123(15) _cell_angle_gamma 90.00 _cell_volume 1734.28(11) _cell_formula_units_Z 8 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 56453 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 3.094 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.490 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56453 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.37 _reflns_number_total 3127 _reflns_number_gt 2843 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogens bonded to gallium were located and refined with isotropic displacement parameters. For the hydrogens bonded to Ga1 all H-H and H-Ga distances were restrained to be equal to obtain reasonable geometries, comparable to those obtained for Ga2, where no restraints applied. All carbon bonded hydrogens were calculated in ideal positions and and refined after a riding model. ; _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^)+(0.0453P)^2^+4.1443P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3127 _refine_ls_number_parameters 191 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.164 _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 Ga1 Ga 0.24303(6) 0.89520(4) 0.93654(4) 0.0492(2) Uani 1 1 d D . . Ga2 Ga -0.70260(6) 0.84799(4) 0.61166(4) 0.04471(19) Uani 1 1 d . . . H23 H -0.724(7) 0.739(5) 0.600(4) 0.075(19) Uiso 1 1 d . . . H22 H -0.727(7) 0.905(5) 0.520(5) 0.08(2) Uiso 1 1 d . . . H21 H -0.778(7) 0.889(4) 0.692(4) 0.067(17) Uiso 1 1 d . . . N11 N 0.2680(4) 0.8910(3) 1.0841(3) 0.0393(8) Uani 1 1 d . . . C12 C 0.1463(5) 0.8914(3) 1.1339(3) 0.0397(10) Uani 1 1 d . . . H12A H 0.0492 0.8901 1.1006 0.048 Uiso 1 1 calc R . . C13 C 0.1595(5) 0.8936(3) 1.2328(3) 0.0408(10) Uani 1 1 d . . . C14 C 0.3007(5) 0.8944(3) 1.2787(3) 0.0389(10) Uani 1 1 d . . . H14A H 0.3122 0.8957 1.3464 0.047 Uiso 1 1 calc R . . C15 C 0.4286(5) 0.8934(3) 1.2286(3) 0.0408(10) Uani 1 1 d . . . C16 C 0.4042(5) 0.8925(3) 1.1303(3) 0.0375(9) Uani 1 1 d . . . H16A H 0.4888 0.8930 1.0940 0.045 Uiso 1 1 calc R . . C17 C 0.0189(6) 0.8944(4) 1.2852(4) 0.0515(12) Uani 1 1 d . . . H17A H 0.0461 0.8846 1.3534 0.077 Uiso 1 1 calc R . . H17B H -0.0484 0.8424 1.2608 0.077 Uiso 1 1 calc R . . H17C H -0.0321 0.9568 1.2753 0.077 Uiso 1 1 calc R . . C18 C 0.5843(6) 0.8924(4) 1.2766(4) 0.0542(13) Uani 1 1 d . . . H18A H 0.6553 0.9122 1.2312 0.081 Uiso 1 1 calc R . . H18B H 0.6091 0.8269 1.2996 0.081 Uiso 1 1 calc R . . H18C H 0.5907 0.9373 1.3306 0.081 Uiso 1 1 calc R . . N21 N -0.4758(4) 0.8587(3) 0.6514(3) 0.0387(8) Uani 1 1 d . . . C22 C -0.3756(5) 0.8648(3) 0.5878(3) 0.0401(10) Uani 1 1 d . . . H22A H -0.4111 0.8704 0.5225 0.048 Uiso 1 1 calc R . . C23 C -0.2218(5) 0.8632(3) 0.6114(3) 0.0398(10) Uani 1 1 d . . . C24 C -0.1731(5) 0.8572(3) 0.7073(4) 0.0417(10) Uani 1 1 d . . . H24A H -0.0685 0.8564 0.7265 0.050 Uiso 1 1 calc R . . C25 C -0.2751(6) 0.8523(3) 0.7755(3) 0.0419(10) Uani 1 1 d . . . C26 C -0.4259(5) 0.8537(3) 0.7442(3) 0.0395(10) Uani 1 1 d . . . H26A H -0.4974 0.8509 0.7901 0.047 Uiso 1 1 calc R . . C27 C -0.1147(6) 0.8702(4) 0.5355(4) 0.0575(13) Uani 1 1 d . . . H27A H -0.0452 0.9241 0.5499 0.086 Uiso 1 1 calc R . . H27B H -0.1712 0.8812 0.4736 0.086 Uiso 1 1 calc R . . H27C H -0.0577 0.8097 0.5334 0.086 Uiso 1 1 calc R . . C28 C -0.2262(6) 0.8446(4) 0.8808(4) 0.0532(13) Uani 1 1 d . . . H28A H -0.3068 0.8682 0.9175 0.080 Uiso 1 1 calc R . . H28B H -0.1359 0.8839 0.8957 0.080 Uiso 1 1 calc R . . H28C H -0.2043 0.7769 0.8972 0.080 Uiso 1 1 calc R . . H12 H 0.170(5) 0.798(3) 0.919(4) 0.080(19) Uiso 1 1 d D . . H11 H 0.147(5) 0.984(3) 0.915(6) 0.12(3) Uiso 1 1 d D . . H13 H 0.408(5) 0.904(3) 0.923(6) 0.11(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0463(3) 0.0630(4) 0.0384(3) -0.0011(2) 0.0050(2) 0.0022(3) Ga2 0.0372(3) 0.0570(4) 0.0401(3) -0.0024(2) 0.0046(2) -0.0016(2) N11 0.037(2) 0.043(2) 0.0380(19) 0.0007(16) 0.0060(16) 0.0017(16) C12 0.034(2) 0.038(2) 0.048(2) 0.000(2) 0.0066(19) -0.0001(18) C13 0.047(3) 0.031(2) 0.046(2) 0.0011(19) 0.016(2) 0.0027(19) C14 0.048(3) 0.032(2) 0.037(2) 0.0016(18) 0.0048(19) -0.0003(19) C15 0.045(3) 0.029(2) 0.047(3) 0.0037(19) -0.001(2) 0.0009(18) C16 0.032(2) 0.038(2) 0.044(2) 0.0003(19) 0.0068(18) 0.0005(18) C17 0.050(3) 0.055(3) 0.053(3) -0.001(2) 0.021(2) -0.002(2) C18 0.051(3) 0.056(3) 0.054(3) 0.005(2) -0.008(2) -0.002(2) N21 0.0357(19) 0.0380(19) 0.042(2) 0.0024(16) 0.0023(16) 0.0000(15) C22 0.044(3) 0.042(2) 0.035(2) -0.0016(19) 0.0038(19) -0.0006(19) C23 0.043(2) 0.033(2) 0.044(2) 0.0006(19) 0.008(2) 0.0006(18) C24 0.039(2) 0.031(2) 0.055(3) 0.000(2) -0.002(2) 0.0003(18) C25 0.055(3) 0.029(2) 0.040(2) 0.0018(18) 0.000(2) 0.000(2) C26 0.049(3) 0.034(2) 0.036(2) -0.0015(18) 0.0067(19) 0.0021(19) C27 0.043(3) 0.069(3) 0.064(3) 0.004(3) 0.019(2) -0.004(2) C28 0.058(3) 0.052(3) 0.047(3) 0.002(2) -0.010(2) 0.006(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 N11 2.073(4) . ? Ga1 H12 1.50(4) . ? Ga1 H11 1.51(4) . ? Ga1 H13 1.51(5) . ? Ga2 N21 2.060(4) . ? Ga2 H23 1.53(6) . ? Ga2 H22 1.51(6) . ? Ga2 H21 1.49(6) . ? N11 C16 1.329(6) . ? N11 C12 1.345(6) . ? C12 C13 1.389(7) . ? C12 H12A 0.9500 . ? C13 C14 1.367(7) . ? C13 C17 1.514(6) . ? C14 C15 1.397(7) . ? C14 H14A 0.9500 . ? C15 C16 1.383(6) . ? C15 C18 1.492(7) . ? C16 H16A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.326(6) . ? N21 C26 1.346(6) . ? C22 C23 1.385(6) . ? C22 H22A 0.9500 . ? C23 C24 1.385(7) . ? C23 C27 1.501(7) . ? C24 C25 1.385(7) . ? C24 H24A 0.9500 . ? C25 C26 1.380(7) . ? C25 C28 1.512(6) . ? C26 H26A 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Ga1 H12 98(2) . . ? N11 Ga1 H11 104(3) . . ? H12 Ga1 H11 117.4(14) . . ? N11 Ga1 H13 96(3) . . ? H12 Ga1 H13 117.6(14) . . ? H11 Ga1 H13 117.2(15) . . ? N21 Ga2 H23 102(2) . . ? N21 Ga2 H22 105(2) . . ? H23 Ga2 H22 115(3) . . ? N21 Ga2 H21 106(2) . . ? H23 Ga2 H21 114(3) . . ? H22 Ga2 H21 114(3) . . ? C16 N11 C12 119.5(4) . . ? C16 N11 Ga1 120.2(3) . . ? C12 N11 Ga1 120.2(3) . . ? N11 C12 C13 121.5(4) . . ? N11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 117.9(4) . . ? C14 C13 C17 122.7(4) . . ? C12 C13 C17 119.4(4) . . ? C13 C14 C15 121.5(4) . . ? C13 C14 H14A 119.2 . . ? C15 C14 H14A 119.2 . . ? C16 C15 C14 116.3(4) . . ? C16 C15 C18 120.8(4) . . ? C14 C15 C18 122.9(4) . . ? N11 C16 C15 123.1(4) . . ? N11 C16 H16A 118.4 . . ? C15 C16 H16A 118.4 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 118.3(4) . . ? C22 N21 Ga2 121.9(3) . . ? C26 N21 Ga2 119.6(3) . . ? N21 C22 C23 123.6(4) . . ? N21 C22 H22A 118.2 . . ? C23 C22 H22A 118.2 . . ? C24 C23 C22 117.0(4) . . ? C24 C23 C27 122.3(4) . . ? C22 C23 C27 120.7(4) . . ? C23 C24 C25 120.8(4) . . ? C23 C24 H24A 119.6 . . ? C25 C24 H24A 119.6 . . ? C26 C25 C24 117.5(4) . . ? C26 C25 C28 120.2(5) . . ? C24 C25 C28 122.3(5) . . ? N21 C26 C25 122.8(4) . . ? N21 C26 H26A 118.6 . . ? C25 C26 H26A 118.6 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.2(7) . . . . ? Ga1 N11 C12 C13 -176.7(3) . . . . ? N11 C12 C13 C14 -0.6(7) . . . . ? N11 C12 C13 C17 179.7(4) . . . . ? C12 C13 C14 C15 0.2(7) . . . . ? C17 C13 C14 C15 179.9(4) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C13 C14 C15 C18 -178.8(4) . . . . ? C12 N11 C16 C15 0.7(7) . . . . ? Ga1 N11 C16 C15 177.6(3) . . . . ? C14 C15 C16 N11 -1.1(6) . . . . ? C18 C15 C16 N11 178.3(4) . . . . ? C26 N21 C22 C23 2.0(7) . . . . ? Ga2 N21 C22 C23 -173.9(3) . . . . ? N21 C22 C23 C24 -1.5(7) . . . . ? N21 C22 C23 C27 179.9(4) . . . . ? C22 C23 C24 C25 0.5(6) . . . . ? C27 C23 C24 C25 179.1(4) . . . . ? C23 C24 C25 C26 0.0(7) . . . . ? C23 C24 C25 C28 179.4(4) . . . . ? C22 N21 C26 C25 -1.5(6) . . . . ? Ga2 N21 C26 C25 174.5(3) . . . . ? C24 C25 C26 N21 0.6(7) . . . . ? C28 C25 C26 N21 -178.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.869 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.093 #======END data_nog38 _database_code_CSD 211301 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 Cl3 Ga N' _chemical_formula_weight 283.22 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.19680(10) _cell_length_b 9.1925(2) _cell_length_c 9.4850(2) _cell_angle_alpha 87.3256(7) _cell_angle_beta 71.9435(8) _cell_angle_gamma 68.3327(12) _cell_volume 552.805(18) _cell_formula_units_Z 2 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 15084 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 3.162 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.390 _exptl_absorpt_correction_T_max 0.790 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15084 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.60 _reflns_number_total 2374 _reflns_number_gt 2351 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0324P)^2^+0.2125P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2374 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Ga1 Ga 0.15617(3) 0.882664(19) 0.219668(19) 0.02686(8) Uani 1 1 d . . . Cl1 Cl -0.14743(8) 0.89185(6) 0.21781(7) 0.04447(14) Uani 1 1 d . . . N1 N 0.1309(2) 1.10149(16) 0.24242(15) 0.0264(3) Uani 1 1 d . . . Cl2 Cl 0.40203(8) 0.77469(6) 0.01530(5) 0.04095(13) Uani 1 1 d . . . C2 C -0.0115(3) 1.2184(2) 0.19596(18) 0.0275(3) Uani 1 1 d . . . H2 H -0.095(4) 1.187(3) 0.150(2) 0.033(5) Uiso 1 1 d . . . Cl3 Cl 0.23652(7) 0.77236(5) 0.41014(5) 0.03564(12) Uani 1 1 d . . . C3 C -0.0395(3) 1.3742(2) 0.21555(18) 0.0291(3) Uani 1 1 d . . . C4 C 0.0878(3) 1.4073(2) 0.2841(2) 0.0306(4) Uani 1 1 d . . . H4 H 0.069(4) 1.510(3) 0.303(2) 0.032(5) Uiso 1 1 d . . . C5 C 0.2364(3) 1.2880(2) 0.33171(19) 0.0306(3) Uani 1 1 d . . . C6 C 0.2517(3) 1.1350(2) 0.30884(19) 0.0284(3) Uani 1 1 d . . . H6 H 0.352(4) 1.049(3) 0.337(2) 0.032(5) Uiso 1 1 d . . . C7 C -0.2048(3) 1.5011(2) 0.1665(2) 0.0371(4) Uani 1 1 d . . . H7C H -0.241(5) 1.465(3) 0.095(3) 0.055(8) Uiso 1 1 d . . . H7B H -0.154(5) 1.580(3) 0.126(3) 0.057(8) Uiso 1 1 d . . . H7A H -0.320(5) 1.541(3) 0.243(3) 0.057(8) Uiso 1 1 d . . . C8 C 0.3762(4) 1.3179(3) 0.4065(3) 0.0406(4) Uani 1 1 d . . . H8C H 0.505(7) 1.281(5) 0.354(5) 0.099(13) Uiso 1 1 d . . . H8B H 0.342(6) 1.423(5) 0.429(4) 0.082(10) Uiso 1 1 d . . . H8A H 0.344(5) 1.282(4) 0.507(4) 0.075(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.02650(13) 0.02507(12) 0.02939(12) 0.00143(7) -0.00943(8) -0.00946(9) Cl1 0.0342(3) 0.0378(2) 0.0701(3) 0.0052(2) -0.0232(2) -0.0177(2) N1 0.0249(7) 0.0264(6) 0.0269(6) 0.0013(5) -0.0061(5) -0.0101(6) Cl2 0.0408(3) 0.0419(2) 0.0296(2) -0.00430(17) -0.00789(18) -0.0054(2) C2 0.0257(8) 0.0299(8) 0.0264(7) 0.0010(6) -0.0070(6) -0.0108(7) Cl3 0.0378(2) 0.0354(2) 0.0303(2) 0.00741(16) -0.01007(17) -0.01113(19) C3 0.0283(8) 0.0283(8) 0.0282(8) 0.0031(6) -0.0049(6) -0.0112(7) C4 0.0298(9) 0.0272(8) 0.0336(8) 0.0001(6) -0.0052(7) -0.0130(7) C5 0.0269(8) 0.0355(9) 0.0304(8) 0.0009(6) -0.0050(7) -0.0161(7) C6 0.0241(8) 0.0311(8) 0.0301(8) 0.0021(6) -0.0077(6) -0.0111(7) C7 0.0366(10) 0.0291(9) 0.0446(10) 0.0055(8) -0.0153(9) -0.0095(8) C8 0.0373(11) 0.0420(11) 0.0496(12) -0.0019(9) -0.0161(9) -0.0201(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 Ga1 N1 1.9677(14) . ? Ga1 Cl2 2.1517(5) . ? Ga1 Cl1 2.1608(5) . ? Ga1 Cl3 2.1610(4) . ? N1 C6 1.343(2) . ? N1 C2 1.350(2) . ? C2 C3 1.384(2) . ? C2 H2 0.98(2) . ? C3 C4 1.396(3) . ? C3 C7 1.504(2) . ? C4 C5 1.392(3) . ? C4 H4 0.92(2) . ? C5 C6 1.391(3) . ? C5 C8 1.503(3) . ? C6 H6 0.95(2) . ? C7 H7C 0.91(3) . ? C7 H7B 0.94(3) . ? C7 H7A 0.88(3) . ? C8 H8C 0.85(4) . ? C8 H8B 0.92(4) . ? C8 H8A 0.98(4) . ? 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 Cl2 108.17(4) . . ? N1 Ga1 Cl1 106.55(4) . . ? Cl2 Ga1 Cl1 112.29(2) . . ? N1 Ga1 Cl3 105.85(4) . . ? Cl2 Ga1 Cl3 111.383(19) . . ? Cl1 Ga1 Cl3 112.19(2) . . ? C6 N1 C2 119.87(14) . . ? C6 N1 Ga1 119.66(11) . . ? C2 N1 Ga1 120.45(12) . . ? N1 C2 C3 122.03(16) . . ? N1 C2 H2 115.9(13) . . ? C3 C2 H2 122.0(13) . . ? C2 C3 C4 117.48(16) . . ? C2 C3 C7 120.22(17) . . ? C4 C3 C7 122.28(16) . . ? C5 C4 C3 121.19(16) . . ? C5 C4 H4 119.0(14) . . ? C3 C4 H4 119.7(14) . . ? C6 C5 C4 117.27(17) . . ? C6 C5 C8 119.64(17) . . ? C4 C5 C8 123.09(17) . . ? N1 C6 C5 122.15(16) . . ? N1 C6 H6 116.9(14) . . ? C5 C6 H6 121.0(14) . . ? C3 C7 H7C 112.9(18) . . ? C3 C7 H7B 109.8(17) . . ? H7C C7 H7B 107(2) . . ? C3 C7 H7A 109.4(18) . . ? H7C C7 H7A 108(3) . . ? H7B C7 H7A 110(3) . . ? C5 C8 H8C 112(3) . . ? C5 C8 H8B 114(2) . . ? H8C C8 H8B 107(4) . . ? C5 C8 H8A 108(2) . . ? H8C C8 H8A 116(3) . . ? H8B C8 H8A 100(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ga1 N1 C6 -87.45(12) . . . . ? Cl1 Ga1 N1 C6 151.62(12) . . . . ? Cl3 Ga1 N1 C6 32.02(13) . . . . ? Cl2 Ga1 N1 C2 94.62(12) . . . . ? Cl1 Ga1 N1 C2 -26.31(13) . . . . ? Cl3 Ga1 N1 C2 -145.90(12) . . . . ? C6 N1 C2 C3 -0.6(2) . . . . ? Ga1 N1 C2 C3 177.36(13) . . . . ? N1 C2 C3 C4 0.8(3) . . . . ? N1 C2 C3 C7 -178.02(17) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C7 C3 C4 C5 178.46(18) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C3 C4 C5 C8 -179.74(18) . . . . ? C2 N1 C6 C5 -0.2(2) . . . . ? Ga1 N1 C6 C5 -178.16(13) . . . . ? C4 C5 C6 N1 0.7(3) . . . . ? C8 C5 C6 N1 -179.92(17) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.489 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.068 #======END data_nog34 _database_code_CSD 211302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 Cl2 Ga N2' _chemical_formula_weight 355.84 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0572(3) _cell_length_b 10.2092(3) _cell_length_c 14.7805(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.1991(11) _cell_angle_gamma 90.00 _cell_volume 1664.02(9) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 38639 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 1.963 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38639 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 25.38 _reflns_number_total 2930 _reflns_number_gt 2686 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0467P)^2^+1.5954P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2930 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 Ga1 Ga 0.25728(3) 0.00261(3) 0.243411(17) 0.02350(13) Uani 1 1 d . . . H1 H 0.330(3) 0.109(3) 0.201(2) 0.042(9) Uiso 1 1 d . . . Cl2 Cl 0.32046(8) -0.20093(7) 0.27136(5) 0.0418(2) Uani 1 1 d . . . Cl3 Cl 0.06973(7) 0.03251(9) 0.28442(5) 0.0445(2) Uani 1 1 d . . . N11 N 0.32945(19) 0.0604(2) 0.37998(13) 0.0223(4) Uani 1 1 d . . . C12 C 0.2865(3) 0.0111(3) 0.45532(18) 0.0239(6) Uani 1 1 d . . . H12 H 0.228(3) -0.056(3) 0.447(2) 0.036(8) Uiso 1 1 d . . . C13 C 0.3272(2) 0.0515(3) 0.54163(17) 0.0251(5) Uani 1 1 d . . . C14 C 0.4166(2) 0.1470(3) 0.54891(17) 0.0253(6) Uani 1 1 d . . . H14 H 0.449(3) 0.178(3) 0.606(2) 0.029(7) Uiso 1 1 d . . . C15 C 0.4631(2) 0.1991(3) 0.47193(18) 0.0251(5) Uani 1 1 d . . . C16 C 0.4160(2) 0.1519(3) 0.38820(17) 0.0242(5) Uani 1 1 d . . . H16 H 0.444(3) 0.184(3) 0.332(2) 0.030(8) Uiso 1 1 d . . . C17 C 0.2745(4) -0.0050(4) 0.6241(2) 0.0376(8) Uani 1 1 d . . . H17C H 0.221(5) -0.063(5) 0.613(3) 0.080(15) Uiso 1 1 d . . . H17B H 0.332(6) -0.024(5) 0.667(4) 0.101(19) Uiso 1 1 d . . . H17A H 0.227(4) 0.050(5) 0.652(3) 0.083(15) Uiso 1 1 d . . . C18 C 0.5593(3) 0.3028(3) 0.4775(3) 0.0387(7) Uani 1 1 d . . . H18C H 0.574(5) 0.337(5) 0.428(4) 0.101(19) Uiso 1 1 d . . . H18B H 0.631(5) 0.277(5) 0.513(4) 0.102(17) Uiso 1 1 d . . . H18A H 0.544(6) 0.368(7) 0.515(4) 0.12(2) Uiso 1 1 d . . . N21 N 0.18311(19) -0.0541(2) 0.10773(13) 0.0225(4) Uani 1 1 d . . . C22 C 0.2157(3) 0.0156(3) 0.03686(18) 0.0231(5) Uani 1 1 d . . . H22 H 0.266(3) 0.089(3) 0.0516(19) 0.025(7) Uiso 1 1 d . . . C23 C 0.1763(3) -0.0141(3) -0.05214(18) 0.0254(6) Uani 1 1 d . . . C24 C 0.0998(2) -0.1206(3) -0.06653(17) 0.0245(5) Uani 1 1 d . . . H24 H 0.069(3) -0.140(3) -0.125(2) 0.025(7) Uiso 1 1 d . . . C25 C 0.0630(2) -0.1931(2) 0.00608(17) 0.0238(5) Uani 1 1 d . . . C26 C 0.1077(2) -0.1560(2) 0.09268(17) 0.0240(5) Uani 1 1 d . . . H26 H 0.087(3) -0.206(3) 0.146(2) 0.028(7) Uiso 1 1 d . . . C27 C 0.2175(3) 0.0659(4) -0.1296(2) 0.0407(8) Uani 1 1 d . . . H27B H 0.162(5) 0.062(5) -0.178(3) 0.083(14) Uiso 1 1 d . . . H27A H 0.218(5) 0.159(6) -0.112(4) 0.114(19) Uiso 1 1 d . . . H27C H 0.296(6) 0.051(6) -0.144(4) 0.103(18) Uiso 1 1 d . . . C28 C -0.0223(3) -0.3064(3) -0.0083(2) 0.0332(7) Uani 1 1 d . . . H28C H -0.002(4) -0.357(5) -0.053(3) 0.078(14) Uiso 1 1 d . . . H28B H -0.027(4) -0.351(4) 0.038(3) 0.068(13) Uiso 1 1 d . . . H28A H -0.103(4) -0.281(4) -0.025(3) 0.060(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0278(2) 0.0277(2) 0.01457(18) -0.00130(10) -0.00165(12) -0.00075(11) Cl2 0.0630(5) 0.0328(4) 0.0264(4) -0.0072(3) -0.0171(3) 0.0136(3) Cl3 0.0299(4) 0.0820(6) 0.0208(4) -0.0111(3) -0.0035(3) 0.0125(4) N11 0.0246(11) 0.0251(11) 0.0167(10) -0.0030(8) -0.0024(8) 0.0009(9) C12 0.0251(15) 0.0280(14) 0.0182(13) 0.0013(10) -0.0016(10) -0.0010(10) C13 0.0279(14) 0.0278(13) 0.0192(12) 0.0007(10) -0.0010(10) 0.0046(11) C14 0.0278(14) 0.0284(13) 0.0184(13) -0.0048(10) -0.0063(10) 0.0065(10) C15 0.0246(14) 0.0255(13) 0.0245(13) -0.0021(10) -0.0024(10) 0.0013(10) C16 0.0266(14) 0.0275(13) 0.0182(13) -0.0010(10) -0.0008(10) 0.0010(10) C17 0.041(2) 0.054(2) 0.0176(15) 0.0032(13) 0.0026(13) -0.0044(15) C18 0.0390(19) 0.0387(17) 0.0372(18) -0.0024(15) -0.0056(14) -0.0125(14) N21 0.0269(12) 0.0260(11) 0.0144(10) -0.0008(8) -0.0004(8) 0.0023(9) C22 0.0246(15) 0.0269(14) 0.0172(13) 0.0000(10) -0.0013(10) -0.0006(10) C23 0.0268(15) 0.0322(14) 0.0169(13) 0.0030(10) 0.0002(10) 0.0004(10) C24 0.0262(14) 0.0310(14) 0.0155(12) -0.0025(10) -0.0035(10) 0.0007(10) C25 0.0258(14) 0.0241(13) 0.0210(13) -0.0011(10) -0.0010(10) 0.0024(10) C26 0.0285(14) 0.0259(13) 0.0175(12) 0.0018(10) 0.0004(10) -0.0007(10) C27 0.043(2) 0.058(2) 0.0198(15) 0.0092(14) -0.0024(13) -0.0173(16) C28 0.0421(19) 0.0286(15) 0.0276(16) -0.0004(13) -0.0053(13) -0.0088(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 N21 2.188(2) . ? Ga1 N11 2.196(2) . ? Ga1 Cl2 2.2214(7) . ? Ga1 Cl3 2.2237(8) . ? Ga1 H1 1.51(3) . ? N11 C16 1.336(3) . ? N11 C12 1.340(3) . ? C12 C13 1.384(4) . ? C12 H12 0.94(3) . ? C13 C14 1.387(4) . ? C13 C17 1.505(4) . ? C14 C15 1.388(4) . ? C14 H14 0.95(3) . ? C15 C16 1.393(4) . ? C15 C18 1.499(4) . ? C16 H16 0.96(3) . ? C17 H17C 0.85(5) . ? C17 H17B 0.89(6) . ? C17 H17A 0.88(5) . ? C18 H18C 0.83(6) . ? C18 H18B 0.95(6) . ? C18 H18A 0.89(7) . ? N21 C22 1.337(3) . ? N21 C26 1.342(3) . ? C22 C23 1.389(4) . ? C22 H22 0.95(3) . ? C23 C24 1.385(4) . ? C23 C27 1.504(4) . ? C24 C25 1.389(4) . ? C24 H24 0.93(3) . ? C25 C26 1.390(4) . ? C25 C28 1.497(4) . ? C26 H26 0.98(3) . ? C27 H27B 0.91(5) . ? C27 H27A 0.99(6) . ? C27 H27C 0.92(6) . ? C28 H28C 0.89(5) . ? C28 H28B 0.83(5) . ? C28 H28A 0.94(4) . ? 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 N21 Ga1 N11 179.28(7) . . ? N21 Ga1 Cl2 90.85(6) . . ? N11 Ga1 Cl2 89.55(6) . . ? N21 Ga1 Cl3 89.52(6) . . ? N11 Ga1 Cl3 89.77(6) . . ? Cl2 Ga1 Cl3 111.38(4) . . ? N21 Ga1 H1 89.1(12) . . ? N11 Ga1 H1 91.1(12) . . ? Cl2 Ga1 H1 125.3(12) . . ? Cl3 Ga1 H1 123.3(12) . . ? C16 N11 C12 118.8(2) . . ? C16 N11 Ga1 118.74(16) . . ? C12 N11 Ga1 122.41(18) . . ? N11 C12 C13 122.9(3) . . ? N11 C12 H12 116.8(19) . . ? C13 C12 H12 120.3(19) . . ? C12 C13 C14 117.6(2) . . ? C12 C13 C17 120.8(3) . . ? C14 C13 C17 121.6(2) . . ? C13 C14 C15 120.7(2) . . ? C13 C14 H14 121.4(18) . . ? C15 C14 H14 117.9(18) . . ? C14 C15 C16 117.3(2) . . ? C14 C15 C18 122.0(3) . . ? C16 C15 C18 120.7(3) . . ? N11 C16 C15 122.8(2) . . ? N11 C16 H16 115.7(17) . . ? C15 C16 H16 121.5(18) . . ? C13 C17 H17C 115(3) . . ? C13 C17 H17B 111(4) . . ? H17C C17 H17B 117(5) . . ? C13 C17 H17A 114(3) . . ? H17C C17 H17A 96(5) . . ? H17B C17 H17A 103(5) . . ? C15 C18 H18C 115(4) . . ? C15 C18 H18B 113(3) . . ? H18C C18 H18B 113(5) . . ? C15 C18 H18A 114(4) . . ? H18C C18 H18A 107(5) . . ? H18B C18 H18A 93(5) . . ? C22 N21 C26 118.9(2) . . ? C22 N21 Ga1 118.22(18) . . ? C26 N21 Ga1 122.93(16) . . ? N21 C22 C23 122.8(2) . . ? N21 C22 H22 115.3(17) . . ? C23 C22 H22 121.9(17) . . ? C24 C23 C22 117.6(2) . . ? C24 C23 C27 121.7(3) . . ? C22 C23 C27 120.7(3) . . ? C23 C24 C25 120.7(2) . . ? C23 C24 H24 119.5(17) . . ? C25 C24 H24 119.7(18) . . ? C24 C25 C26 117.5(2) . . ? C24 C25 C28 121.3(2) . . ? C26 C25 C28 121.2(2) . . ? N21 C26 C25 122.6(2) . . ? N21 C26 H26 116.9(17) . . ? C25 C26 H26 120.5(17) . . ? C23 C27 H27B 111(3) . . ? C23 C27 H27A 109(3) . . ? H27B C27 H27A 104(4) . . ? C23 C27 H27C 116(4) . . ? H27B C27 H27C 114(5) . . ? H27A C27 H27C 103(5) . . ? C25 C28 H28C 111(3) . . ? C25 C28 H28B 112(3) . . ? H28C C28 H28B 110(5) . . ? C25 C28 H28A 113(2) . . ? H28C C28 H28A 105(4) . . ? H28B C28 H28A 105(4) . . ? 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 N21 Ga1 N11 C16 -118(6) . . . . ? Cl2 Ga1 N11 C16 119.18(18) . . . . ? Cl3 Ga1 N11 C16 -129.43(18) . . . . ? N21 Ga1 N11 C12 59(6) . . . . ? Cl2 Ga1 N11 C12 -63.6(2) . . . . ? Cl3 Ga1 N11 C12 47.8(2) . . . . ? C16 N11 C12 C13 0.5(4) . . . . ? Ga1 N11 C12 C13 -176.7(2) . . . . ? N11 C12 C13 C14 -0.2(4) . . . . ? N11 C12 C13 C17 178.8(3) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C17 C13 C14 C15 -179.2(3) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C13 C14 C15 C18 179.7(3) . . . . ? C12 N11 C16 C15 -0.5(4) . . . . ? Ga1 N11 C16 C15 176.88(19) . . . . ? C14 C15 C16 N11 0.1(4) . . . . ? C18 C15 C16 N11 -179.4(3) . . . . ? N11 Ga1 N21 C22 109(6) . . . . ? Cl2 Ga1 N21 C22 -127.58(19) . . . . ? Cl3 Ga1 N21 C22 121.04(19) . . . . ? N11 Ga1 N21 C26 -71(6) . . . . ? Cl2 Ga1 N21 C26 51.74(19) . . . . ? Cl3 Ga1 N21 C26 -59.64(19) . . . . ? C26 N21 C22 C23 -1.0(4) . . . . ? Ga1 N21 C22 C23 178.3(2) . . . . ? N21 C22 C23 C24 0.2(4) . . . . ? N21 C22 C23 C27 -178.8(3) . . . . ? C22 C23 C24 C25 1.0(4) . . . . ? C27 C23 C24 C25 180.0(3) . . . . ? C23 C24 C25 C26 -1.2(4) . . . . ? C23 C24 C25 C28 178.4(3) . . . . ? C22 N21 C26 C25 0.7(4) . . . . ? Ga1 N21 C26 C25 -178.61(19) . . . . ? C24 C25 C26 N21 0.4(4) . . . . ? C28 C25 C26 N21 -179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.441 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.069 #======END data_alex2 _database_code_CSD 211303 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl4 Ga N2' _chemical_formula_weight 370.73 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 Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 9.0480(4) _cell_length_b 12.1395(7) _cell_length_c 13.4546(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1477.83(13) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 22132 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.564 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.629 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22132 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.43 _reflns_number_total 1367 _reflns_number_gt 1316 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. All hydrogen atoms were calculated in ideal positions but all parameters were refined, except for H24A which was refined after a riding model. ; _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^)+(0.0057P)^2^+1.5245P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(15) _refine_ls_number_reflns 1367 _refine_ls_number_parameters 110 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0560 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.113 _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 Ga1 Ga 0.0000 -0.97928(4) -0.02166(4) 0.02242(13) Uani 1 2 d S . . Cl1 Cl 0.0000 -0.98744(12) 0.13966(10) 0.0378(4) Uani 1 2 d S . . Cl2 Cl 0.0000 -1.14685(10) -0.08127(11) 0.0324(3) Uani 1 2 d S . . Cl3 Cl -0.19872(10) -0.89508(7) -0.07224(8) 0.0320(2) Uani 1 1 d . . . N11 N 0.0000 -0.6422(3) 0.0294(4) 0.0273(10) Uani 1 2 d S . . C12 C -0.1268(4) -0.6396(3) 0.0800(3) 0.0293(9) Uani 1 1 d . . . H12A H -0.215(4) -0.638(3) 0.047(3) 0.030(10) Uiso 1 1 d . . . C13 C -0.1330(5) -0.6338(3) 0.1826(3) 0.0282(10) Uani 1 1 d . . . H13A H -0.226(4) -0.632(3) 0.222(3) 0.021(9) Uiso 1 1 d . . . C14 C 0.0000 -0.6314(4) 0.2346(4) 0.0278(13) Uani 1 2 d S . . H14A H 0.0000 -0.620(5) 0.296(5) 0.033(18) Uiso 1 2 d S . . N21 N 0.0000 -0.6452(3) -0.1718(4) 0.0250(9) Uani 1 2 d S . . H21A H 0.0000 -0.654(6) -0.102(6) 0.05(2) Uiso 1 2 d S . . C22 C -0.1279(5) -0.6450(3) -0.2209(3) 0.0280(10) Uani 1 1 d . . . H22A H -0.205(5) -0.638(3) -0.183(3) 0.027(10) Uiso 1 1 d . . . C23 C -0.1308(5) -0.6441(3) -0.3222(3) 0.0305(9) Uani 1 1 d . . . H23A H -0.217(5) -0.642(3) -0.355(3) 0.027(10) Uiso 1 1 d . . . C24 C 0.0000 -0.6443(4) -0.3735(4) 0.0261(11) Uani 1 2 d S . . H24A H 0.0000 -0.6445 -0.4441 0.031 Uiso 1 2 calc SR . . 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 0.0206(2) 0.0244(2) 0.0223(3) 0.0002(3) 0.000 0.000 Cl1 0.0274(8) 0.0611(10) 0.0249(8) 0.0030(6) 0.000 0.000 Cl2 0.0300(6) 0.0238(6) 0.0434(8) -0.0047(5) 0.000 0.000 Cl3 0.0293(4) 0.0357(5) 0.0310(5) 0.0007(4) -0.0045(4) 0.0084(3) N11 0.032(2) 0.022(2) 0.028(2) -0.0028(18) 0.000 0.000 C12 0.025(2) 0.032(2) 0.031(3) -0.0005(15) -0.0010(15) 0.0008(15) C13 0.032(3) 0.023(2) 0.031(3) -0.0012(17) 0.0072(17) -0.0012(16) C14 0.046(4) 0.018(3) 0.020(3) -0.002(2) 0.000 0.000 N21 0.031(3) 0.024(2) 0.020(3) 0.0027(17) 0.000 0.000 C22 0.028(2) 0.023(2) 0.033(3) 0.0017(16) 0.0067(19) 0.0033(16) C23 0.035(3) 0.0235(19) 0.032(2) 0.0007(16) -0.0096(18) -0.0027(16) C24 0.043(3) 0.019(3) 0.017(3) -0.0008(19) 0.000 0.000 _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 Cl1 2.1728(14) . ? Ga1 Cl3 2.1774(9) 4 ? Ga1 Cl3 2.1774(9) . ? Ga1 Cl2 2.1866(13) . ? N11 C12 1.335(5) 4 ? N11 C12 1.335(5) . ? C12 C13 1.382(5) . ? C12 H12A 0.92(4) . ? C13 C14 1.393(6) . ? C13 H13A 1.00(4) . ? C14 C13 1.393(6) 4 ? C14 H14A 0.84(7) . ? N21 C22 1.333(5) . ? N21 C22 1.333(5) 4 ? N21 H21A 0.95(8) . ? C22 C23 1.363(6) . ? C22 H22A 0.86(4) . ? C23 C24 1.370(5) . ? C23 H23A 0.90(4) . ? C24 C23 1.370(5) 4 ? C24 H24A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ga1 Cl3 109.49(4) . 4 ? Cl1 Ga1 Cl3 109.49(4) . . ? Cl3 Ga1 Cl3 111.34(5) 4 . ? Cl1 Ga1 Cl2 108.91(6) . . ? Cl3 Ga1 Cl2 108.79(4) 4 . ? Cl3 Ga1 Cl2 108.79(4) . . ? C12 N11 C12 118.5(5) 4 . ? N11 C12 C13 123.0(4) . . ? N11 C12 H12A 120(3) . . ? C13 C12 H12A 117(3) . . ? C12 C13 C14 117.9(4) . . ? C12 C13 H13A 125(2) . . ? C14 C13 H13A 117(2) . . ? C13 C14 C13 119.5(5) . 4 ? C13 C14 H14A 120.0(4) . . ? C13 C14 H14A 120.0(4) 4 . ? C22 N21 C22 120.5(6) . 4 ? C22 N21 H21A 119.6(4) . . ? C22 N21 H21A 119.6(4) 4 . ? N21 C22 C23 120.9(4) . . ? N21 C22 H22A 114(3) . . ? C23 C22 H22A 125(3) . . ? C22 C23 C24 119.2(4) . . ? C22 C23 H23A 120(3) . . ? C24 C23 H23A 120(3) . . ? C23 C24 C23 119.5(6) . 4 ? C23 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 4 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N11 C12 C13 0.4(7) 4 . . . ? N11 C12 C13 C14 -0.5(6) . . . . ? C12 C13 C14 C13 0.6(7) . . . 4 ? C22 N21 C22 C23 -0.3(7) 4 . . . ? N21 C22 C23 C24 0.5(6) . . . . ? C22 C23 C24 C23 -0.7(7) . . . 4 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21 H21A N11 0.95(8) 1.77(8) 2.706(6) 169(6) . _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.328 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.066