# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef 'compound-1-WX8-12C.CIF' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Xiao-Ying Huang' _publ_contact_author_address ; State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences Fuzhou, Fujian 350002 P. R. CHINA ; _publ_contact_author_email xyhuang@fjirsm.ac.cn _publ_contact_author_phone 86-59183793727 _publ_contact_author_fax 86-59183793727 loop_ _publ_author_name _publ_author_address 'Wei-Wei Xiong' ; State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences Fuzhou, Fujian 350002 Graduate School of the Chinese Academy of Sciences Beijing, 10049 P. R. CHINA ; 'Jian-Rong Li' ; State Key Lab of Structural Chemistry Fujian Institute of Reseach on the Structure of Matter, Chinese Academy of Sciences Fuzhou 350002 P. R. CHINA ; 'Mei-Ling Feng' ; State Key Lab of Structural Chemistry Fujian Institute of Reseach on the Structure of Matter, Chinese Academy of Sciences Fuzhou 350002 P. R. CHINA ; 'Xiao-Ying Huang' ; State Key Lab of Structural Chemistry Fujian Institute of Reseach on the Structure of Matter, Chinese Academy of Sciences Fuzhou 350002 P. R. CHINA ; _publ_section_title ; Solvothermal Syntheses, Crystal Structures, and Characterizations of a Series of One-Dimensional Organic-containing Gallium Polyselenides ; data_compound-1-wx8-12c _database_code_depnum_ccdc_archive 'CCDC 810662' #TrackingRef 'compound-1-WX8-12C.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Ga2 Se7, C3 H12 N2' _chemical_formula_sum 'C3 H12 Ga2 N2 Se7' _chemical_formula_weight 768.31 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5724(2) _cell_length_b 12.3856(3) _cell_length_c 8.0889(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.120(2) _cell_angle_gamma 90.00 _cell_volume 756.69(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2134 _cell_measurement_theta_min 2.5194 _cell_measurement_theta_max 26.74 _exptl_crystal_description Prism _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 20.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.35065 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3118 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 26.74 _reflns_number_total 2615 _reflns_number_gt 2252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2003' _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^)+(0.0229P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 938 friedel pairs' _refine_ls_abs_structure_Flack 0.07(3) _refine_ls_number_reflns 2615 _refine_ls_number_parameters 128 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0541 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 Ga2 Ga 0.54660(13) 0.05837(7) 0.38376(11) 0.0210(2) Uani 1 1 d . . . Ga1 Ga 0.61528(12) 0.28334(7) 0.65550(11) 0.0186(2) Uani 1 1 d . . . Se1 Se 0.72778(11) 0.46370(7) 0.67096(11) 0.0238(2) Uani 1 1 d . . . Se2 Se 0.48603(12) 0.24757(7) 0.38451(10) 0.0254(2) Uani 1 1 d . . . Se4 Se 0.69505(13) 0.00310(7) 0.64359(11) 0.0263(2) Uani 1 1 d . . . Se3 Se 0.86012(12) 0.16120(7) 0.70874(10) 0.0235(2) Uani 1 1 d . . . Se5 Se 0.41998(12) 0.24726(8) 0.87454(10) 0.0262(2) Uani 1 1 d . . . Se6 Se 0.18006(12) 0.35375(7) 0.77161(11) 0.0266(2) Uani 1 1 d . . . Se7 Se 0.26325(13) 0.53088(7) 0.84196(11) 0.0288(2) Uani 1 1 d . . . N1 N 1.0477(11) 0.2509(9) 0.3586(9) 0.070(3) Uani 1 1 d . . . H1A H 1.1543 0.2255 0.3919 0.106 Uiso 1 1 calc R . . H1B H 0.9656 0.2024 0.3799 0.106 Uiso 1 1 calc R . . H1C H 1.0279 0.3119 0.4125 0.106 Uiso 1 1 calc R . . N2 N 0.6556(11) 0.4650(7) 0.0978(10) 0.049(2) Uani 1 1 d . . . H2A H 0.6340 0.5323 0.1292 0.073 Uiso 1 1 calc R . . H2B H 0.5736 0.4210 0.1337 0.073 Uiso 1 1 calc R . . H2C H 0.6526 0.4620 -0.0123 0.073 Uiso 1 1 calc R . . C1 C 1.0400(12) 0.2721(9) 0.1816(11) 0.042(3) Uani 1 1 d . . . H1D H 1.0612 0.2053 0.1236 0.051 Uiso 1 1 calc R . . H1E H 1.1336 0.3223 0.1587 0.051 Uiso 1 1 calc R . . C2 C 0.8640(12) 0.3185(7) 0.1157(11) 0.034(2) Uani 1 1 d . . . H2D H 0.8574 0.3164 -0.0045 0.040 Uiso 1 1 calc R . . H2E H 0.7696 0.2734 0.1523 0.040 Uiso 1 1 calc R . . C3 C 0.8350(13) 0.4308(7) 0.1697(13) 0.040(3) Uani 1 1 d . . . H3A H 0.9256 0.4778 0.1306 0.048 Uiso 1 1 calc R . . H3B H 0.8403 0.4346 0.2897 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga2 0.0227(6) 0.0152(5) 0.0247(5) -0.0033(4) -0.0011(4) 0.0006(4) Ga1 0.0187(5) 0.0149(5) 0.0223(5) -0.0013(4) 0.0015(4) 0.0014(4) Se1 0.0203(5) 0.0166(4) 0.0341(5) 0.0005(4) -0.0014(4) -0.0020(4) Se2 0.0333(6) 0.0174(5) 0.0245(5) -0.0011(4) -0.0040(4) 0.0041(5) Se4 0.0319(6) 0.0168(5) 0.0290(5) 0.0014(4) -0.0069(4) -0.0006(4) Se3 0.0199(5) 0.0176(5) 0.0322(5) -0.0006(4) -0.0028(4) 0.0023(4) Se5 0.0270(5) 0.0241(5) 0.0283(5) 0.0057(4) 0.0068(4) -0.0004(5) Se6 0.0219(6) 0.0249(5) 0.0335(5) 0.0024(4) 0.0060(4) -0.0036(4) Se7 0.0300(6) 0.0236(5) 0.0337(5) -0.0010(4) 0.0088(4) 0.0040(4) N1 0.033(5) 0.140(10) 0.039(5) 0.022(6) 0.006(4) 0.004(7) N2 0.050(6) 0.044(6) 0.052(6) -0.018(5) 0.006(4) 0.016(5) C1 0.036(6) 0.051(7) 0.039(6) -0.001(5) 0.005(4) -0.005(6) C2 0.029(6) 0.033(6) 0.039(6) 0.007(4) 0.005(4) 0.008(5) C3 0.037(7) 0.028(6) 0.053(7) -0.017(5) -0.008(5) -0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga2 Se2 2.3880(12) . ? Ga2 Se1 2.3991(12) 2_646 ? Ga2 Se4 2.4105(12) . ? Ga2 Se7 2.4291(13) 2_646 ? Ga1 Se2 2.3772(12) . ? Ga1 Se1 2.3908(12) . ? Ga1 Se3 2.4077(12) . ? Ga1 Se5 2.4295(11) . ? Se1 Ga2 2.3991(12) 2_656 ? Se4 Se3 2.3621(12) . ? Se5 Se6 2.3486(13) . ? Se6 Se7 2.3415(13) . ? Se7 Ga2 2.4291(13) 2_656 ? N1 C1 1.453(11) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C3 1.501(11) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? C1 C2 1.513(12) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 C3 1.478(11) . ? C2 H2D 0.9700 . ? C2 H2E 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 Se2 Ga2 Se1 108.43(5) . 2_646 ? Se2 Ga2 Se4 110.74(5) . . ? Se1 Ga2 Se4 111.44(5) 2_646 . ? Se2 Ga2 Se7 105.30(4) . 2_646 ? Se1 Ga2 Se7 110.19(5) 2_646 2_646 ? Se4 Ga2 Se7 110.56(5) . 2_646 ? Se2 Ga1 Se1 110.12(5) . . ? Se2 Ga1 Se3 107.97(4) . . ? Se1 Ga1 Se3 108.11(5) . . ? Se2 Ga1 Se5 113.97(5) . . ? Se1 Ga1 Se5 111.53(4) . . ? Se3 Ga1 Se5 104.79(4) . . ? Ga1 Se1 Ga2 98.42(4) . 2_656 ? Ga1 Se2 Ga2 96.82(4) . . ? Se3 Se4 Ga2 99.51(4) . . ? Se4 Se3 Ga1 95.32(4) . . ? Se6 Se5 Ga1 97.71(4) . . ? Se7 Se6 Se5 104.61(5) . . ? Se6 Se7 Ga2 96.45(4) . 2_656 ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C3 N2 H2A 109.5 . . ? C3 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C3 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? N1 C1 C2 112.8(8) . . ? N1 C1 H1D 109.0 . . ? C2 C1 H1D 109.0 . . ? N1 C1 H1E 109.0 . . ? C2 C1 H1E 109.0 . . ? H1D C1 H1E 107.8 . . ? C3 C2 C1 113.5(8) . . ? C3 C2 H2D 108.9 . . ? C1 C2 H2D 108.9 . . ? C3 C2 H2E 108.9 . . ? C1 C2 H2E 108.9 . . ? H2D C2 H2E 107.7 . . ? C2 C3 N2 107.5(7) . . ? C2 C3 H3A 110.2 . . ? N2 C3 H3A 110.2 . . ? C2 C3 H3B 110.2 . . ? N2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? 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 Se2 Ga1 Se1 Ga2 62.90(5) . . . 2_656 ? Se3 Ga1 Se1 Ga2 -179.35(4) . . . 2_656 ? Se5 Ga1 Se1 Ga2 -64.66(5) . . . 2_656 ? Se1 Ga1 Se2 Ga2 150.12(5) . . . . ? Se3 Ga1 Se2 Ga2 32.29(5) . . . . ? Se5 Ga1 Se2 Ga2 -83.68(5) . . . . ? Se1 Ga2 Se2 Ga1 123.32(5) 2_646 . . . ? Se4 Ga2 Se2 Ga1 0.76(6) . . . . ? Se7 Ga2 Se2 Ga1 -118.76(5) 2_646 . . . ? Se2 Ga2 Se4 Se3 -32.96(6) . . . . ? Se1 Ga2 Se4 Se3 -153.75(4) 2_646 . . . ? Se7 Ga2 Se4 Se3 83.35(5) 2_646 . . . ? Ga2 Se4 Se3 Ga1 48.20(5) . . . . ? Se2 Ga1 Se3 Se4 -53.38(5) . . . . ? Se1 Ga1 Se3 Se4 -172.49(4) . . . . ? Se5 Ga1 Se3 Se4 68.46(5) . . . . ? Se2 Ga1 Se5 Se6 -53.90(6) . . . . ? Se1 Ga1 Se5 Se6 71.55(5) . . . . ? Se3 Ga1 Se5 Se6 -171.72(5) . . . . ? Ga1 Se5 Se6 Se7 -78.19(5) . . . . ? Se5 Se6 Se7 Ga2 79.92(5) . . . 2_656 ? N1 C1 C2 C3 70.7(12) . . . . ? C1 C2 C3 N2 -179.1(8) . . . . ? 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 H1B Se3 0.89 2.88 3.442(8) 122.9 . C2 H2E Se2 0.97 2.97 3.819(9) 146.8 . N1 H1A Se2 0.89 2.53 3.311(8) 146.5 1_655 N2 H2A Se5 0.89 2.69 3.552(8) 162.4 2_656 N2 H2C Se1 0.89 2.66 3.534(8) 166.0 1_554 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.74 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.706 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.179 # Attachment 'compound-2-wx8-17f.cif' data_compound-2-wx8-17f _database_code_depnum_ccdc_archive 'CCDC 810663' #TrackingRef 'compound-2-wx8-17f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H14 N2, Ga2 Se5' _chemical_formula_sum 'C4 H14 Ga2 N2 Se5' _chemical_formula_weight 624.41 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.7660(4) _cell_length_b 11.7743(4) _cell_length_c 10.9763(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.170(4) _cell_angle_gamma 90.00 _cell_volume 1427.36(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4264 _cell_measurement_theta_min 2.5234 _cell_measurement_theta_max 28.8815 _exptl_crystal_description Prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.906 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 16.490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.27247 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7807 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.74 _reflns_number_total 1525 _reflns_number_gt 1245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2003' _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^)+(0.0150P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1525 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0183 _refine_ls_wR_factor_ref 0.0374 _refine_ls_wR_factor_gt 0.0369 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.62229(3) 0.76965(3) 0.89974(3) 0.02017(10) Uani 1 1 d . . . Se1 Se 0.5000 0.63260(4) 0.7500 0.02248(12) Uani 1 2 d S . . Se2 Se 0.51341(3) 0.94820(3) 0.86213(3) 0.02464(10) Uani 1 1 d . . . Se3 Se 0.81917(3) 0.78126(3) 0.87513(3) 0.02262(9) Uani 1 1 d . . . N1 N 0.7192(3) 0.5638(3) 0.6262(3) 0.0414(8) Uani 1 1 d . . . H1C H 0.7064 0.4893 0.6268 0.062 Uiso 1 1 calc R . . H1D H 0.6851 0.5984 0.6770 0.062 Uiso 1 1 calc R . . H1E H 0.7984 0.5775 0.6555 0.062 Uiso 1 1 calc R . . C1 C 0.6647(4) 0.6079(3) 0.4907(4) 0.0432(10) Uani 1 1 d . . . H1A H 0.7005 0.5686 0.4351 0.052 Uiso 1 1 calc R . . H1B H 0.5785 0.5921 0.4588 0.052 Uiso 1 1 calc R . . C2 C 0.6842(3) 0.7330(3) 0.4839(4) 0.0360(9) Uani 1 1 d . . . H2A H 0.6523 0.7712 0.5435 0.043 Uiso 1 1 calc R . . H2B H 0.6385 0.7593 0.3970 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.01736(18) 0.0222(2) 0.01729(18) 0.00120(15) 0.00136(14) -0.00022(17) Se1 0.0187(2) 0.0198(3) 0.0239(2) 0.000 0.0009(2) 0.000 Se2 0.0281(2) 0.0234(2) 0.02136(18) -0.00226(14) 0.00720(15) 0.00336(16) Se3 0.02092(17) 0.0287(2) 0.01744(16) 0.00132(15) 0.00554(13) -0.00156(16) N1 0.049(2) 0.0251(19) 0.058(2) 0.0025(16) 0.0289(18) 0.0075(16) C1 0.042(2) 0.041(3) 0.046(2) -0.0038(19) 0.014(2) -0.007(2) C2 0.038(2) 0.037(2) 0.035(2) 0.0028(17) 0.0140(18) 0.004(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 Se1 2.3969(5) . ? Ga1 Se3 2.4014(5) 7_667 ? Ga1 Se2 2.4221(5) . ? Ga1 Se3 2.4268(5) . ? Se1 Ga1 2.3969(5) 2_656 ? Se2 Se2 2.3712(6) 2_656 ? Se3 Ga1 2.4014(5) 7_667 ? N1 C1 1.495(4) . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? C1 C2 1.497(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C2 1.518(7) 7_666 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? 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 Se1 Ga1 Se3 115.399(19) . 7_667 ? Se1 Ga1 Se2 108.078(17) . . ? Se3 Ga1 Se2 109.831(18) 7_667 . ? Se1 Ga1 Se3 109.389(16) . . ? Se3 Ga1 Se3 100.515(16) 7_667 . ? Se2 Ga1 Se3 113.656(19) . . ? Ga1 Se1 Ga1 95.36(2) . 2_656 ? Se2 Se2 Ga1 92.876(14) 2_656 . ? Ga1 Se3 Ga1 79.485(16) 7_667 . ? C1 N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C1 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C2 C1 N1 111.8(3) . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? N1 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C2 114.2(4) . 7_666 ? C1 C2 H2A 108.7 . . ? C2 C2 H2A 108.7 7_666 . ? C1 C2 H2B 108.7 . . ? C2 C2 H2B 108.7 7_666 . ? H2A C2 H2B 107.6 . . ? 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 Se3 Ga1 Se1 Ga1 143.72(2) 7_667 . . 2_656 ? Se2 Ga1 Se1 Ga1 20.347(10) . . . 2_656 ? Se3 Ga1 Se1 Ga1 -103.871(17) . . . 2_656 ? Se1 Ga1 Se2 Se2 -53.79(2) . . . 2_656 ? Se3 Ga1 Se2 Se2 179.533(18) 7_667 . . 2_656 ? Se3 Ga1 Se2 Se2 67.83(2) . . . 2_656 ? Se1 Ga1 Se3 Ga1 -121.86(2) . . . 7_667 ? Se3 Ga1 Se3 Ga1 0.0 7_667 . . 7_667 ? Se2 Ga1 Se3 Ga1 117.26(2) . . . 7_667 ? N1 C1 C2 C2 65.9(5) . . . 7_666 ? 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 H1D Se1 0.89 2.60 3.401(3) 150.6 . N1 H1E Se2 0.89 2.75 3.390(3) 130.1 4_646 N1 H1C Se3 0.89 2.47 3.357(3) 176.9 4_646 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.74 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.374 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.118 # Attachment 'compound-3-xh1-28c.cif' data_compound-3-xh1-28c _database_code_depnum_ccdc_archive 'CCDC 810664' #TrackingRef 'compound-3-xh1-28c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Ga2 Se6, 2(C2 H8 N)' _chemical_formula_sum 'C4 H16 Ga2 N2 Se6' _chemical_formula_weight 705.39 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' Se Se -0.0929 2.2259 '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 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.135(12) _cell_length_b 8.456(7) _cell_length_c 14.066(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.318(17) _cell_angle_gamma 90.00 _cell_volume 1654(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1403 _cell_measurement_theta_min 2.8194 _cell_measurement_theta_max 27.4758 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.2800 _exptl_crystal_size_mid 0.1700 _exptl_crystal_size_min 0.1300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 16.433 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3135 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku SCXmini' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12394 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3774 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2003' _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^)+(0.0600P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3774 _refine_ls_number_parameters 137 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.088 _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 0.22218(7) 0.69867(11) 0.57495(6) 0.0338(2) Uani 1 1 d . . . Ga2 Ga 0.23447(7) 0.80356(11) 0.82589(6) 0.0339(2) Uani 1 1 d . . . Se1 Se 0.18675(7) 0.91817(10) 0.67027(5) 0.0405(2) Uani 1 1 d . . . Se2 Se 0.11269(6) 0.67855(12) 0.42525(6) 0.0436(3) Uani 1 1 d . . . Se3 Se 0.19970(7) 0.46129(11) 0.66420(6) 0.0452(2) Uani 1 1 d . . . Se4 Se 0.29060(7) 0.53450(12) 0.81563(6) 0.0472(3) Uani 1 1 d . . . Se5 Se 0.37069(7) 0.95041(11) 0.91297(6) 0.0431(2) Uani 1 1 d . . . Se6 Se 0.38562(7) 0.78292(12) 1.04877(6) 0.0461(3) Uani 1 1 d . . . N1 N 0.4142(6) 0.2929(9) 0.6270(5) 0.0479(19) Uani 1 1 d . . . H1A H 0.3607 0.3509 0.6263 0.057 Uiso 1 1 calc R . . H1B H 0.4588 0.3558 0.6081 0.057 Uiso 1 1 calc R . . C1 C 0.4499(10) 0.2386(17) 0.7262(8) 0.081(4) Uani 1 1 d U . . H1C H 0.4631 0.3284 0.7683 0.121 Uiso 1 1 calc R . . H1D H 0.5078 0.1785 0.7278 0.121 Uiso 1 1 calc R . . H1E H 0.4021 0.1734 0.7474 0.121 Uiso 1 1 calc R . . C2 C 0.3924(9) 0.1624(14) 0.5583(8) 0.071(3) Uani 1 1 d U . . H2A H 0.3666 0.2039 0.4954 0.106 Uiso 1 1 calc R . . H2B H 0.3461 0.0934 0.5789 0.106 Uiso 1 1 calc R . . H2C H 0.4502 0.1044 0.5553 0.106 Uiso 1 1 calc R . . N2A N 0.0410(9) 0.2820(14) 0.3962(8) 0.052(3) Uani 0.670(14) 1 d PD A 1 H2D H -0.0218 0.2759 0.4002 0.063 Uiso 0.670(14) 1 calc PR A 1 H2E H 0.0613 0.3784 0.4180 0.063 Uiso 0.670(14) 1 calc PR A 1 C3A C 0.0473(16) 0.276(3) 0.2954(12) 0.061(5) Uani 0.670(14) 1 d PD A 1 H3A H 0.0037 0.3514 0.2605 0.092 Uiso 0.670(14) 1 calc PR A 1 H3B H 0.0307 0.1717 0.2709 0.092 Uiso 0.670(14) 1 calc PR A 1 H3C H 0.1118 0.3004 0.2876 0.092 Uiso 0.670(14) 1 calc PR A 1 C4A C 0.0910(13) 0.168(3) 0.4633(12) 0.059(6) Uani 0.670(14) 1 d PD A 1 H4A H 0.0763 0.1863 0.5264 0.089 Uiso 0.670(14) 1 calc PR A 1 H4B H 0.1591 0.1783 0.4658 0.089 Uiso 0.670(14) 1 calc PR A 1 H4C H 0.0711 0.0631 0.4423 0.089 Uiso 0.670(14) 1 calc PR A 1 N2B N 0.0660(18) 0.158(3) 0.3624(17) 0.052(3) Uani 0.33 1 d PD A 2 H2F H 0.0896 0.0711 0.3379 0.063 Uiso 0.330(14) 1 calc PR A 2 H2G H 0.0033 0.1431 0.3641 0.063 Uiso 0.330(14) 1 calc PR A 2 C3B C 0.081(4) 0.298(6) 0.309(3) 0.061(5) Uani 0.33 1 d PD A 2 H3D H 0.0418 0.2924 0.2454 0.092 Uiso 0.330(14) 1 calc PR A 2 H3E H 0.1476 0.3039 0.3023 0.092 Uiso 0.330(14) 1 calc PR A 2 H3F H 0.0641 0.3894 0.3418 0.092 Uiso 0.330(14) 1 calc PR A 2 C4B C 0.120(3) 0.197(8) 0.457(2) 0.059(6) Uani 0.33 1 d PD A 2 H4D H 0.1090 0.1176 0.5023 0.089 Uiso 0.330(14) 1 calc PR A 2 H4E H 0.0993 0.2979 0.4765 0.089 Uiso 0.330(14) 1 calc PR A 2 H4F H 0.1872 0.2012 0.4537 0.089 Uiso 0.330(14) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0388(5) 0.0447(5) 0.0189(4) -0.0009(3) 0.0077(3) 0.0014(4) Ga2 0.0405(5) 0.0427(5) 0.0192(4) -0.0002(3) 0.0076(4) -0.0001(4) Se1 0.0598(6) 0.0413(5) 0.0222(4) 0.0034(3) 0.0121(4) 0.0084(4) Se2 0.0363(5) 0.0734(7) 0.0214(4) -0.0040(4) 0.0059(3) -0.0007(4) Se3 0.0592(6) 0.0406(5) 0.0368(5) -0.0013(4) 0.0116(4) -0.0069(4) Se4 0.0620(6) 0.0455(5) 0.0332(4) 0.0064(4) 0.0061(4) 0.0073(4) Se5 0.0469(5) 0.0508(6) 0.0333(4) -0.0003(4) 0.0116(4) -0.0107(4) Se6 0.0380(5) 0.0651(6) 0.0353(5) 0.0078(4) 0.0071(4) 0.0043(4) N1 0.055(5) 0.044(5) 0.044(4) -0.001(3) 0.007(4) 0.000(4) C1 0.090(7) 0.098(7) 0.056(6) 0.016(6) 0.019(5) 0.028(6) C2 0.078(7) 0.070(6) 0.064(6) -0.007(5) 0.015(5) -0.016(5) N2A 0.052(7) 0.046(6) 0.060(7) 0.000(5) 0.012(5) 0.004(5) C3A 0.066(17) 0.068(11) 0.052(9) -0.009(7) 0.019(9) -0.035(9) C4A 0.055(14) 0.070(13) 0.057(7) 0.010(7) 0.021(8) 0.003(10) N2B 0.052(7) 0.046(6) 0.060(7) 0.000(5) 0.012(5) 0.004(5) C3B 0.066(17) 0.068(11) 0.052(9) -0.009(7) 0.019(9) -0.035(9) C4B 0.055(14) 0.070(13) 0.057(7) 0.010(7) 0.021(8) 0.003(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 Se2 2.385(2) . ? Ga1 Se1 2.3946(19) . ? Ga1 Se6 2.409(2) 4_575 ? Ga1 Se3 2.418(2) . ? Ga2 Se1 2.378(2) . ? Ga2 Se2 2.4085(19) 4_576 ? Ga2 Se4 2.422(2) . ? Ga2 Se5 2.4301(19) . ? Se2 Ga2 2.4085(19) 4_575 ? Se3 Se4 2.364(2) . ? Se5 Se6 2.357(2) . ? Se6 Ga1 2.409(2) 4_576 ? N1 C2 1.463(12) . ? N1 C1 1.469(13) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C1 H1E 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N2A C3A 1.438(16) . ? N2A C4A 1.443(17) . ? N2A H2D 0.9000 . ? N2A H2E 0.9000 . ? C3A H3A 0.9600 . ? C3A H3B 0.9600 . ? C3A H3C 0.9600 . ? C4A H4A 0.9600 . ? C4A H4B 0.9600 . ? C4A H4C 0.9600 . ? N2B C3B 1.440(17) . ? N2B C4B 1.443(17) . ? N2B H2F 0.9000 . ? N2B H2G 0.9000 . ? C3B H3D 0.9600 . ? C3B H3E 0.9600 . ? C3B H3F 0.9600 . ? C4B H4D 0.9600 . ? C4B H4E 0.9600 . ? C4B H4F 0.9600 . ? 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 Se2 Ga1 Se1 112.45(6) . . ? Se2 Ga1 Se6 110.98(7) . 4_575 ? Se1 Ga1 Se6 109.76(5) . 4_575 ? Se2 Ga1 Se3 105.92(6) . . ? Se1 Ga1 Se3 107.01(8) . . ? Se6 Ga1 Se3 110.60(5) 4_575 . ? Se1 Ga2 Se2 113.21(7) . 4_576 ? Se1 Ga2 Se4 111.71(5) . . ? Se2 Ga2 Se4 111.67(5) 4_576 . ? Se1 Ga2 Se5 108.92(6) . . ? Se2 Ga2 Se5 105.04(7) 4_576 . ? Se4 Ga2 Se5 105.76(7) . . ? Ga2 Se1 Ga1 98.40(7) . . ? Ga1 Se2 Ga2 95.14(8) . 4_575 ? Se4 Se3 Ga1 98.60(7) . . ? Se3 Se4 Ga2 99.71(5) . . ? Se6 Se5 Ga2 92.82(7) . . ? Se5 Se6 Ga1 97.82(5) . 4_576 ? C2 N1 C1 112.8(9) . . ? C2 N1 H1A 109.0 . . ? C1 N1 H1A 109.0 . . ? C2 N1 H1B 109.0 . . ? C1 N1 H1B 109.0 . . ? H1A N1 H1B 107.8 . . ? N1 C1 H1C 109.5 . . ? N1 C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? N1 C1 H1E 109.5 . . ? H1C C1 H1E 109.5 . . ? H1D C1 H1E 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3A N2A C4A 120.7(19) . . ? C3A N2A H2D 107.1 . . ? C4A N2A H2D 107.1 . . ? C3A N2A H2E 107.1 . . ? C4A N2A H2E 107.1 . . ? H2D N2A H2E 106.8 . . ? N2A C3A H3A 109.5 . . ? N2A C3A H3B 109.5 . . ? H3A C3A H3B 109.5 . . ? N2A C3A H3C 109.5 . . ? H3A C3A H3C 109.5 . . ? H3B C3A H3C 109.5 . . ? N2A C4A H4A 109.5 . . ? N2A C4A H4B 109.5 . . ? H4A C4A H4B 109.5 . . ? N2A C4A H4C 109.5 . . ? H4A C4A H4C 109.5 . . ? H4B C4A H4C 109.5 . . ? C3B N2B C4B 101(4) . . ? C3B N2B H2F 111.6 . . ? C4B N2B H2F 111.6 . . ? C3B N2B H2G 111.6 . . ? C4B N2B H2G 111.6 . . ? H2F N2B H2G 109.4 . . ? N2B C3B H3D 109.5 . . ? N2B C3B H3E 109.5 . . ? H3D C3B H3E 109.5 . . ? N2B C3B H3F 109.5 . . ? H3D C3B H3F 109.5 . . ? H3E C3B H3F 109.5 . . ? N2B C4B H4D 109.5 . . ? N2B C4B H4E 109.5 . . ? H4D C4B H4E 109.5 . . ? N2B C4B H4F 109.5 . . ? H4D C4B H4F 109.5 . . ? H4E C4B H4F 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 Se2 Ga2 Se1 Ga1 -127.93(5) 4_576 . . . ? Se4 Ga2 Se1 Ga1 -0.83(6) . . . . ? Se5 Ga2 Se1 Ga1 115.62(7) . . . . ? Se2 Ga1 Se1 Ga2 146.19(5) . . . . ? Se6 Ga1 Se1 Ga2 -89.75(6) 4_575 . . . ? Se3 Ga1 Se1 Ga2 30.30(6) . . . . ? Se1 Ga1 Se2 Ga2 121.79(6) . . . 4_575 ? Se6 Ga1 Se2 Ga2 -1.59(6) 4_575 . . 4_575 ? Se3 Ga1 Se2 Ga2 -121.66(5) . . . 4_575 ? Se2 Ga1 Se3 Se4 -169.45(5) . . . . ? Se1 Ga1 Se3 Se4 -49.29(7) . . . . ? Se6 Ga1 Se3 Se4 70.22(7) 4_575 . . . ? Ga1 Se3 Se4 Ga2 44.18(7) . . . . ? Se1 Ga2 Se4 Se3 -28.67(7) . . . . ? Se2 Ga2 Se4 Se3 99.26(8) 4_576 . . . ? Se5 Ga2 Se4 Se3 -147.02(5) . . . . ? Se1 Ga2 Se5 Se6 -177.99(4) . . . . ? Se2 Ga2 Se5 Se6 60.44(7) 4_576 . . . ? Se4 Ga2 Se5 Se6 -57.80(6) . . . . ? Ga2 Se5 Se6 Ga1 -53.27(7) . . . 4_576 ? 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 H1A Se3 0.90 2.60 3.473(9) 163.2 . N2A H2E Se2 0.90 2.64 3.506(12) 162.7 . N1 H1B Se5 0.90 2.61 3.456(9) 157.7 2_646 N2A H2D Se1 0.90 2.88 3.609(13) 139.3 3_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.079 _refine_diff_density_min -1.180 _refine_diff_density_rms 0.204 # Attachment 'compound-4-wx5-28a.cif' data_compound-4-wx5-28a _database_code_depnum_ccdc_archive 'CCDC 810665' #TrackingRef 'compound-4-wx5-28a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C6 H16 N3), Ga2 Se6' _chemical_formula_sum 'C12 H32 Ga2 N6 Se6' _chemical_formula_weight 873.64 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_space_group_name_Hall 'P -2yac' _absolute_structure_configuration unk loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 6.9815(19) _cell_length_b 15.436(4) _cell_length_c 11.831(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.462(4) _cell_angle_gamma 90.00 _cell_volume 1274.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3821 _cell_measurement_theta_min 2.1700 _cell_measurement_theta_max 27.4816 _exptl_crystal_description Prism _exptl_crystal_colour red _exptl_crystal_size_max 0.176 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.127 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 10.692 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5819 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11035 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5219 _reflns_number_gt 4287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2003' _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^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.46(2) _refine_ls_number_reflns 5219 _refine_ls_number_parameters 236 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.91213(12) 0.74259(5) 0.67305(8) 0.02601(19) Uani 1 1 d . . . Ga2 Ga 0.40835(11) 0.77880(5) 0.68032(8) 0.0267(2) Uani 1 1 d . . . Se1 Se 0.63009(11) 0.69910(5) 0.57006(8) 0.0332(2) Uani 1 1 d . . . Se2 Se 0.82742(12) 0.81816(6) 0.84430(8) 0.0370(2) Uani 1 1 d . . . Se3 Se 0.58248(12) 0.90138(5) 0.75571(8) 0.0377(3) Uani 1 1 d . . . Se4 Se 0.13836(12) 0.82317(6) 0.56838(8) 0.0396(2) Uani 1 1 d . . . Se5 Se 0.30500(11) 0.69499(5) 0.84249(7) 0.0329(2) Uani 1 1 d . . . Se6 Se 0.08343(11) 0.61210(5) 0.73380(8) 0.0319(2) Uani 1 1 d . . . N1 N 0.6920(11) 0.8975(4) 0.4130(6) 0.0397(19) Uani 1 1 d . . . H1A H 0.6682 0.8519 0.4519 0.048 Uiso 1 1 d R . . H1B H 0.7601 0.9318 0.4548 0.048 Uiso 1 1 d R . . N2 N 0.5098(10) 0.8718(4) 0.1966(6) 0.0355(17) Uani 1 1 d . . . N3 N 0.3951(12) 0.9771(5) 0.0116(7) 0.048(2) Uani 1 1 d . . . H3A H 0.4826 0.9593 -0.0327 0.073 Uiso 1 1 d R . . H3B H 0.4478 0.9990 0.0716 0.073 Uiso 1 1 d R . . C1 C 0.5135(13) 0.9398(5) 0.3820(8) 0.044(2) Uani 1 1 d . . . H1C H 0.5408 0.9965 0.3510 0.052 Uiso 1 1 calc R . . H1D H 0.4391 0.9480 0.4493 0.052 Uiso 1 1 calc R . . C2 C 0.3958(13) 0.8887(5) 0.2962(8) 0.041(2) Uani 1 1 d . . . H2A H 0.3561 0.8343 0.3293 0.049 Uiso 1 1 calc R . . H2B H 0.2817 0.9211 0.2745 0.049 Uiso 1 1 calc R . . C3 C 0.8027(14) 0.8727(6) 0.3128(8) 0.049(3) Uani 1 1 d . . . H3C H 0.9116 0.8374 0.3364 0.059 Uiso 1 1 calc R . . H3D H 0.8506 0.9243 0.2763 0.059 Uiso 1 1 calc R . . C4 C 0.6747(14) 0.8217(6) 0.2293(8) 0.044(2) Uani 1 1 d . . . H4C H 0.7467 0.8072 0.1629 0.053 Uiso 1 1 calc R . . H4D H 0.6342 0.7681 0.2642 0.053 Uiso 1 1 calc R . . C5 C 0.3967(15) 0.8343(5) 0.1041(8) 0.050(3) Uani 1 1 d . . . H5A H 0.3153 0.7891 0.1334 0.061 Uiso 1 1 calc R . . H5B H 0.4819 0.8081 0.0503 0.061 Uiso 1 1 calc R . . C6 C 0.2740(13) 0.9013(6) 0.0444(9) 0.048(3) Uani 1 1 d . . . H6C H 0.2137 0.8761 -0.0226 0.058 Uiso 1 1 calc R . . H6D H 0.1739 0.9205 0.0939 0.058 Uiso 1 1 calc R . . N4 N 0.6981(11) 0.4130(4) 0.9126(6) 0.0398(19) Uani 1 1 d . . . H4A H 0.7094 0.4710 0.9146 0.048 Uiso 1 1 d R . . H4B H 0.7400 0.3919 0.9798 0.048 Uiso 1 1 d R . . N5 N 0.5403(10) 0.3890(4) 0.6886(6) 0.0357(17) Uani 1 1 d . . . N6 N 0.2290(10) 0.4115(4) 0.4267(6) 0.0364(17) Uani 1 1 d . . . H6A H 0.1146 0.3902 0.4067 0.055 Uiso 1 1 d R . . H6B H 0.3168 0.3913 0.3804 0.055 Uiso 1 1 d R . . C7 C 0.4956(15) 0.3894(6) 0.8938(8) 0.050(3) Uani 1 1 d . . . H7A H 0.4190 0.4138 0.9532 0.060 Uiso 1 1 calc R . . H7B H 0.4815 0.3269 0.8954 0.060 Uiso 1 1 calc R . . C8 C 0.4275(14) 0.4243(6) 0.7796(7) 0.041(2) Uani 1 1 d . . . H8A H 0.2938 0.4093 0.7668 0.049 Uiso 1 1 calc R . . H8B H 0.4377 0.4870 0.7796 0.049 Uiso 1 1 calc R . . C9 C 0.8163(13) 0.3782(6) 0.8225(8) 0.049(3) Uani 1 1 d . . . H9A H 0.8102 0.3154 0.8228 0.059 Uiso 1 1 calc R . . H9B H 0.9487 0.3953 0.8354 0.059 Uiso 1 1 calc R . . C10 C 0.7441(12) 0.4125(6) 0.7092(8) 0.043(2) Uani 1 1 d . . . H10A H 0.7576 0.4750 0.7077 0.051 Uiso 1 1 calc R . . H10B H 0.8209 0.3886 0.6496 0.051 Uiso 1 1 calc R . . C11 C 0.4763(13) 0.4202(5) 0.5778(7) 0.038(2) Uani 1 1 d . . . H11A H 0.5689 0.4037 0.5219 0.046 Uiso 1 1 calc R . . H11B H 0.4691 0.4830 0.5790 0.046 Uiso 1 1 calc R . . C12 C 0.2787(13) 0.3829(6) 0.5437(8) 0.040(2) Uani 1 1 d . . . H12A H 0.2822 0.3201 0.5471 0.048 Uiso 1 1 calc R . . H12B H 0.1828 0.4033 0.5953 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0178(4) 0.0325(5) 0.0278(5) 0.0022(4) 0.0010(3) 0.0015(4) Ga2 0.0179(4) 0.0313(5) 0.0311(5) 0.0024(5) 0.0006(4) 0.0001(4) Se1 0.0211(4) 0.0420(5) 0.0365(5) -0.0120(5) 0.0002(4) 0.0001(4) Se2 0.0396(6) 0.0404(5) 0.0309(5) -0.0068(4) -0.0030(4) 0.0023(4) Se3 0.0353(5) 0.0270(5) 0.0509(7) -0.0051(4) 0.0039(5) 0.0005(4) Se4 0.0206(4) 0.0557(6) 0.0423(6) 0.0226(5) 0.0003(4) 0.0017(5) Se5 0.0305(5) 0.0385(5) 0.0293(5) 0.0061(4) -0.0045(4) -0.0019(4) Se6 0.0259(5) 0.0301(4) 0.0397(6) 0.0017(4) -0.0006(4) 0.0014(4) N1 0.051(5) 0.037(4) 0.030(5) -0.005(3) -0.008(4) -0.007(3) N2 0.043(5) 0.037(4) 0.026(4) -0.002(3) -0.001(3) 0.004(3) N3 0.067(6) 0.050(5) 0.027(4) 0.000(4) -0.006(4) -0.004(4) C1 0.055(6) 0.034(5) 0.042(6) -0.007(4) 0.001(5) 0.004(4) C2 0.047(6) 0.033(5) 0.043(6) 0.000(4) 0.001(5) 0.004(4) C3 0.048(6) 0.047(6) 0.051(7) -0.010(5) -0.005(5) 0.005(5) C4 0.060(7) 0.045(5) 0.028(5) -0.008(4) -0.001(5) 0.011(5) C5 0.078(8) 0.028(5) 0.044(6) -0.006(4) -0.015(5) -0.007(5) C6 0.049(6) 0.047(6) 0.049(7) 0.001(5) -0.016(5) 0.009(5) N4 0.052(5) 0.035(4) 0.032(5) 0.005(3) -0.016(4) -0.001(3) N5 0.038(4) 0.044(4) 0.026(4) -0.001(3) -0.003(3) 0.006(3) N6 0.033(4) 0.041(4) 0.034(4) -0.003(3) -0.005(3) 0.000(3) C7 0.069(7) 0.050(6) 0.030(6) 0.003(4) 0.009(5) -0.017(5) C8 0.043(6) 0.056(6) 0.023(5) -0.007(4) 0.007(4) 0.008(4) C9 0.041(6) 0.052(6) 0.054(7) -0.001(5) -0.012(5) 0.022(5) C10 0.037(6) 0.050(6) 0.041(6) -0.009(4) -0.004(5) 0.007(4) C11 0.051(6) 0.037(5) 0.027(5) 0.005(4) -0.004(4) -0.003(4) C12 0.047(6) 0.037(5) 0.037(6) 0.019(4) -0.008(4) -0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 Se4 2.3822(13) 1_655 ? Ga1 Se1 2.3854(12) . ? Ga1 Se2 2.4241(14) . ? Ga1 Se6 2.4413(12) 1_655 ? Ga2 Se4 2.3767(12) . ? Ga2 Se1 2.3905(13) . ? Ga2 Se3 2.4079(12) . ? Ga2 Se5 2.4385(13) . ? Se2 Se3 2.3624(13) . ? Se4 Ga1 2.3822(13) 1_455 ? Se5 Se6 2.3626(12) . ? Se6 Ga1 2.4413(12) 1_455 ? N1 C1 1.446(11) . ? N1 C3 1.481(12) . ? N1 H1A 0.8600 . ? N1 H1B 0.8599 . ? N2 C4 1.432(11) . ? N2 C5 1.453(10) . ? N2 C2 1.463(11) . ? N3 C6 1.500(12) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C1 C2 1.511(12) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.532(12) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C4 H4C 0.9700 . ? C4 H4D 0.9700 . ? C5 C6 1.507(12) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6C 0.9700 . ? C6 H6D 0.9700 . ? N4 C9 1.466(12) . ? N4 C7 1.471(11) . ? N4 H4A 0.9001 . ? N4 H4B 0.9000 . ? N5 C8 1.456(11) . ? N5 C11 1.456(10) . ? N5 C10 1.482(10) . ? N6 C12 1.485(10) . ? N6 H6A 0.8900 . ? N6 H6B 0.8900 . ? C7 C8 1.520(12) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.516(12) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.539(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 Se4 Ga1 Se1 115.53(5) 1_655 . ? Se4 Ga1 Se2 111.25(5) 1_655 . ? Se1 Ga1 Se2 110.28(5) . . ? Se4 Ga1 Se6 104.92(5) 1_655 1_655 ? Se1 Ga1 Se6 108.06(4) . 1_655 ? Se2 Ga1 Se6 106.21(5) . 1_655 ? Se4 Ga2 Se1 111.08(5) . . ? Se4 Ga2 Se3 111.45(5) . . ? Se1 Ga2 Se3 106.18(5) . . ? Se4 Ga2 Se5 110.18(5) . . ? Se1 Ga2 Se5 111.41(5) . . ? Se3 Ga2 Se5 106.39(5) . . ? Ga1 Se1 Ga2 96.55(5) . . ? Se3 Se2 Ga1 94.59(5) . . ? Se2 Se3 Ga2 95.16(4) . . ? Ga2 Se4 Ga1 94.98(5) . 1_455 ? Se6 Se5 Ga2 93.54(5) . . ? Se5 Se6 Ga1 91.29(4) . 1_455 ? C1 N1 C3 112.2(7) . . ? C1 N1 H1A 109.2 . . ? C3 N1 H1A 109.2 . . ? C1 N1 H1B 109.2 . . ? C3 N1 H1B 109.1 . . ? H1A N1 H1B 107.9 . . ? C4 N2 C5 113.9(7) . . ? C4 N2 C2 109.1(7) . . ? C5 N2 C2 112.4(8) . . ? C6 N3 H3A 108.8 . . ? C6 N3 H3B 109.0 . . ? H3A N3 H3B 109.5 . . ? N1 C1 C2 112.6(7) . . ? N1 C1 H1C 109.1 . . ? C2 C1 H1C 109.1 . . ? N1 C1 H1D 109.1 . . ? C2 C1 H1D 109.1 . . ? H1C C1 H1D 107.8 . . ? N2 C2 C1 109.7(8) . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N1 C3 C4 109.9(8) . . ? N1 C3 H3C 109.7 . . ? C4 C3 H3C 109.7 . . ? N1 C3 H3D 109.7 . . ? C4 C3 H3D 109.7 . . ? H3C C3 H3D 108.2 . . ? N2 C4 C3 110.4(7) . . ? N2 C4 H4C 109.6 . . ? C3 C4 H4C 109.6 . . ? N2 C4 H4D 109.6 . . ? C3 C4 H4D 109.6 . . ? H4C C4 H4D 108.1 . . ? N2 C5 C6 111.7(7) . . ? N2 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N2 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N3 C6 C5 109.8(7) . . ? N3 C6 H6C 109.7 . . ? C5 C6 H6C 109.7 . . ? N3 C6 H6D 109.7 . . ? C5 C6 H6D 109.7 . . ? H6C C6 H6D 108.2 . . ? C9 N4 C7 110.9(7) . . ? C9 N4 H4A 109.5 . . ? C7 N4 H4A 109.5 . . ? C9 N4 H4B 109.5 . . ? C7 N4 H4B 109.5 . . ? H4A N4 H4B 108.0 . . ? C8 N5 C11 112.5(7) . . ? C8 N5 C10 108.8(7) . . ? C11 N5 C10 109.8(7) . . ? C12 N6 H6A 109.0 . . ? C12 N6 H6B 108.7 . . ? H6A N6 H6B 109.5 . . ? N4 C7 C8 108.9(8) . . ? N4 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N4 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N5 C8 C7 111.2(7) . . ? N5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N4 C9 C10 109.6(7) . . ? N4 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N4 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? N5 C10 C9 110.9(8) . . ? N5 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? N5 C11 C12 111.4(7) . . ? N5 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N5 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N6 C12 C11 108.6(7) . . ? N6 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? N6 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.3 . . ? 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 Se4 Ga1 Se1 Ga2 -117.43(5) 1_655 . . . ? Se2 Ga1 Se1 Ga2 9.77(6) . . . . ? Se6 Ga1 Se1 Ga2 125.45(5) 1_655 . . . ? Se4 Ga2 Se1 Ga1 149.06(5) . . . . ? Se3 Ga2 Se1 Ga1 27.73(5) . . . . ? Se5 Ga2 Se1 Ga1 -87.69(5) . . . . ? Se4 Ga1 Se2 Se3 86.20(5) 1_655 . . . ? Se1 Ga1 Se2 Se3 -43.34(6) . . . . ? Se6 Ga1 Se2 Se3 -160.18(4) 1_655 . . . ? Ga1 Se2 Se3 Ga2 55.43(5) . . . . ? Se4 Ga2 Se3 Se2 -177.13(5) . . . . ? Se1 Ga2 Se3 Se2 -56.04(5) . . . . ? Se5 Ga2 Se3 Se2 62.74(5) . . . . ? Se1 Ga2 Se4 Ga1 117.62(5) . . . 1_455 ? Se3 Ga2 Se4 Ga1 -124.20(5) . . . 1_455 ? Se5 Ga2 Se4 Ga1 -6.33(6) . . . 1_455 ? Se4 Ga2 Se5 Se6 44.56(6) . . . . ? Se1 Ga2 Se5 Se6 -79.20(5) . . . . ? Se3 Ga2 Se5 Se6 165.50(4) . . . . ? Ga2 Se5 Se6 Ga1 -58.72(5) . . . 1_455 ? C3 N1 C1 C2 51.5(11) . . . . ? C4 N2 C2 C1 61.1(9) . . . . ? C5 N2 C2 C1 -171.4(7) . . . . ? N1 C1 C2 N2 -55.8(10) . . . . ? C1 N1 C3 C4 -51.2(10) . . . . ? C5 N2 C4 C3 170.6(8) . . . . ? C2 N2 C4 C3 -62.8(10) . . . . ? N1 C3 C4 N2 57.4(10) . . . . ? C4 N2 C5 C6 -158.6(9) . . . . ? C2 N2 C5 C6 76.5(10) . . . . ? N2 C5 C6 N3 51.8(12) . . . . ? C9 N4 C7 C8 -58.4(10) . . . . ? C11 N5 C8 C7 179.1(7) . . . . ? C10 N5 C8 C7 -59.0(10) . . . . ? N4 C7 C8 N5 59.4(10) . . . . ? C7 N4 C9 C10 58.3(10) . . . . ? C8 N5 C10 C9 58.3(9) . . . . ? C11 N5 C10 C9 -178.2(7) . . . . ? N4 C9 C10 N5 -58.1(10) . . . . ? C8 N5 C11 C12 -69.3(10) . . . . ? C10 N5 C11 C12 169.4(8) . . . . ? N5 C11 C12 N6 -175.6(7) . . . . ? 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 H1A Se1 0.86 2.76 3.614(7) 173.8 . N1 H1B N3 0.86 1.81 2.653(10) 165.0 2_575 N3 H3A Se3 0.86 2.76 3.528(9) 148.7 1_554 N3 H3B N2 0.86 2.49 2.824(10) 104.1 . N4 H4A N6 0.90 1.82 2.723(9) 176.9 2_565 N6 H6A Se5 0.89 2.63 3.508(7) 171.2 2_464 N6 H6B Se6 0.89 2.58 3.429(8) 160.5 2_564 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.899 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.141 # Attachment 'compound-5-wx8-11c.cif' data_compound-5-wx8-11c _database_code_depnum_ccdc_archive 'CCDC 810666' #TrackingRef 'compound-5-wx8-11c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H16 N3, Ga Se3' _chemical_formula_sum 'C6 H16 Ga N3 Se3' _chemical_formula_weight 436.82 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.623(5) _cell_length_b 16.495(8) _cell_length_c 7.163(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.935(12) _cell_angle_gamma 90.00 _cell_volume 1250.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3753 _cell_measurement_theta_min 2.4696 _cell_measurement_theta_max 27.4700 _exptl_crystal_description needle _exptl_crystal_colour Red _exptl_crystal_size_max 0.212 _exptl_crystal_size_mid 0.078 _exptl_crystal_size_min 0.058 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 10.898 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4074 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10434 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2839 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2003' _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^)+(0.0580P)^2^+0.9954P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2839 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.14473(6) 0.73746(4) 0.56195(9) 0.03238(19) Uani 1 1 d . . . Se1 Se 0.32496(6) 0.68197(5) 0.98380(10) 0.0498(2) Uani 1 1 d . . . Se2 Se 0.23028(7) 0.61638(4) 0.71596(9) 0.0425(2) Uani 1 1 d . . . Se3 Se 0.01727(6) 0.70380(4) 0.28461(9) 0.0413(2) Uani 1 1 d . . . N1 N 0.5398(6) 0.4324(4) 0.5896(9) 0.069(2) Uani 1 1 d . . . H1A H 0.5716 0.4481 0.7028 0.104 Uiso 1 1 calc R . . H1B H 0.5048 0.4747 0.5280 0.104 Uiso 0.50 1 calc PR . . H1E H 0.6012 0.4123 0.5264 0.104 Uiso 1 1 calc R . . N2 N 0.0772(5) 0.4456(4) 0.0971(8) 0.0508(15) Uani 1 1 d . . . H2A H 0.0313 0.4837 0.0321 0.061 Uiso 0.50 1 calc PR . . H2B H 0.0316 0.3996 0.0946 0.061 Uiso 1 1 calc R . . N3 N 0.3093(4) 0.4019(3) 0.3152(7) 0.0339(11) Uani 1 1 d . . . C1 C 0.4436(8) 0.3699(6) 0.6086(11) 0.069(2) Uani 1 1 d . . . H1C H 0.3771 0.3916 0.6790 0.083 Uiso 1 1 calc R . . H1D H 0.4813 0.3241 0.6773 0.083 Uiso 1 1 calc R . . C2 C 0.3881(7) 0.3423(4) 0.4195(11) 0.0535(19) Uani 1 1 d . . . H2C H 0.4566 0.3272 0.3453 0.064 Uiso 1 1 calc R . . H2D H 0.3379 0.2941 0.4358 0.064 Uiso 1 1 calc R . . C3 C 0.1050(6) 0.4725(5) 0.2920(10) 0.0534(19) Uani 1 1 d . . . H3A H 0.0266 0.4777 0.3510 0.064 Uiso 1 1 calc R . . H3B H 0.1450 0.5254 0.2931 0.064 Uiso 1 1 calc R . . C4 C 0.1910(6) 0.4135(5) 0.4028(9) 0.0463(17) Uani 1 1 d . . . H4A H 0.2095 0.4339 0.5292 0.056 Uiso 1 1 calc R . . H4B H 0.1483 0.3618 0.4106 0.056 Uiso 1 1 calc R . . C5 C 0.1957(6) 0.4314(5) 0.0097(9) 0.0480(17) Uani 1 1 d . . . H5A H 0.2396 0.4826 -0.0016 0.058 Uiso 1 1 calc R . . H5B H 0.1765 0.4097 -0.1153 0.058 Uiso 1 1 calc R . . C6 C 0.2804(7) 0.3732(4) 0.1234(9) 0.0445(16) Uani 1 1 d . . . H6A H 0.2394 0.3207 0.1258 0.053 Uiso 1 1 calc R . . H6B H 0.3585 0.3664 0.0641 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0384(4) 0.0383(4) 0.0198(4) 0.0010(3) -0.0009(3) 0.0017(3) Se1 0.0399(4) 0.0664(5) 0.0409(5) -0.0059(3) -0.0099(3) 0.0125(3) Se2 0.0558(4) 0.0384(4) 0.0329(4) 0.0016(3) 0.0006(3) 0.0086(3) Se3 0.0464(4) 0.0545(4) 0.0222(4) 0.0005(3) -0.0013(3) -0.0156(3) N1 0.049(4) 0.097(6) 0.059(5) -0.018(4) -0.010(3) 0.007(4) N2 0.041(3) 0.063(4) 0.046(4) -0.010(3) -0.011(3) 0.006(3) N3 0.029(2) 0.038(3) 0.033(3) 0.004(2) -0.004(2) 0.003(2) C1 0.058(5) 0.095(7) 0.053(5) 0.032(5) -0.007(4) 0.017(5) C2 0.058(4) 0.041(4) 0.059(5) 0.011(3) -0.009(4) 0.001(3) C3 0.037(4) 0.067(5) 0.054(5) -0.020(4) -0.004(3) 0.019(3) C4 0.040(3) 0.065(5) 0.032(4) -0.007(3) -0.001(3) 0.004(3) C5 0.049(4) 0.062(5) 0.032(4) -0.005(3) -0.001(3) -0.003(3) C6 0.047(4) 0.050(4) 0.037(4) -0.003(3) 0.004(3) 0.003(3) _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 Se3 2.3717(13) . ? Ga1 Se3 2.3849(12) 4_576 ? Ga1 Se2 2.4206(13) . ? Ga1 Se1 2.4350(13) 4_575 ? Se1 Se2 2.3517(13) . ? Se1 Ga1 2.4350(13) 4_576 ? Se3 Ga1 2.3849(12) 4_575 ? N1 C1 1.465(11) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1E 0.8900 . ? N2 C3 1.470(9) . ? N2 C5 1.472(8) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C2 1.455(8) . ? N3 C6 1.461(8) . ? N3 C4 1.465(8) . ? C1 C2 1.501(11) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 H2C 0.9700 . ? C2 H2D 0.9700 . ? C3 C4 1.512(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.506(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 Se3 Ga1 Se3 109.83(5) . 4_576 ? Se3 Ga1 Se2 110.70(4) . . ? Se3 Ga1 Se2 104.06(4) 4_576 . ? Se3 Ga1 Se1 109.80(4) . 4_575 ? Se3 Ga1 Se1 115.78(5) 4_576 4_575 ? Se2 Ga1 Se1 106.46(5) . 4_575 ? Se2 Se1 Ga1 98.57(4) . 4_576 ? Se1 Se2 Ga1 96.30(5) . . ? Ga1 Se3 Ga1 98.57(5) . 4_575 ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1E 109.5 . . ? H1A N1 H1E 109.5 . . ? H1B N1 H1E 109.5 . . ? C3 N2 C5 110.0(5) . . ? C3 N2 H2A 109.7 . . ? C5 N2 H2A 109.7 . . ? C3 N2 H2B 109.7 . . ? C5 N2 H2B 109.7 . . ? H2A N2 H2B 108.2 . . ? C2 N3 C6 109.2(5) . . ? C2 N3 C4 110.2(5) . . ? C6 N3 C4 109.1(5) . . ? N1 C1 C2 110.7(6) . . ? N1 C1 H1C 109.5 . . ? C2 C1 H1C 109.5 . . ? N1 C1 H1D 109.5 . . ? C2 C1 H1D 109.5 . . ? H1C C1 H1D 108.1 . . ? N3 C2 C1 114.9(6) . . ? N3 C2 H2C 108.5 . . ? C1 C2 H2C 108.5 . . ? N3 C2 H2D 108.5 . . ? C1 C2 H2D 108.5 . . ? H2C C2 H2D 107.5 . . ? N2 C3 C4 111.6(6) . . ? N2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N3 C4 C3 111.2(6) . . ? N3 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N3 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N2 C5 C6 111.4(6) . . ? N2 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N2 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N3 C6 C5 111.6(5) . . ? N3 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? 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 Ga1 Se1 Se2 Ga1 49.86(4) 4_576 . . . ? Se3 Ga1 Se2 Se1 -174.48(3) . . . . ? Se3 Ga1 Se2 Se1 -56.55(5) 4_576 . . . ? Se1 Ga1 Se2 Se1 66.23(4) 4_575 . . . ? Se3 Ga1 Se3 Ga1 131.74(6) 4_576 . . 4_575 ? Se2 Ga1 Se3 Ga1 -113.91(4) . . . 4_575 ? Se1 Ga1 Se3 Ga1 3.34(4) 4_575 . . 4_575 ? C6 N3 C2 C1 169.9(6) . . . . ? C4 N3 C2 C1 -70.3(8) . . . . ? N1 C1 C2 N3 -69.6(9) . . . . ? C5 N2 C3 C4 -54.7(8) . . . . ? C2 N3 C4 C3 -177.5(6) . . . . ? C6 N3 C4 C3 -57.6(7) . . . . ? N2 C3 C4 N3 57.2(8) . . . . ? C3 N2 C5 C6 54.5(8) . . . . ? C2 N3 C6 C5 178.4(6) . . . . ? C4 N3 C6 C5 57.9(7) . . . . ? N2 C5 C6 N3 -57.3(8) . . . . ? 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 H1E Se2 0.89 2.64 3.511(6) 165.8 3_666 N1 H1B N1 0.89 1.79 2.674(14) 170.4 3_666 N2 H2A N2 0.90 1.83 2.729(12) 173.8 3_565 C5 H5B Se3 0.97 2.96 3.704(7) 134.0 3_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.682 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.127