# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jay Kochi' 'Jianjiang Lu' 'S.V. Rosokha' 'T.Y. Rosokha' _publ_contact_author_name 'Jay Kochi' _publ_contact_author_address ; Chemistry University of Houston 4800 Calhoun Rd Fleming Bldg Houston TX 77204 UNITED STATES OF AMERICA ; _publ_contact_author_email JKOCHI@UH.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Halogen-bonded assembly of hybrid inorganic/organic 3D-networks from dibromocuprate salts and tetrabromomethane ; data_I _database_code_depnum_ccdc_archive 'CCDC 644447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H28 N, C Br4, Br2 Cu' _chemical_formula_sum 'C13 H28 Br6 Cu N' _chemical_formula_weight 741.36 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.298(14) _cell_length_b 10.536(16) _cell_length_c 13.75(3) _cell_angle_alpha 92.04(6) _cell_angle_beta 103.73(7) _cell_angle_gamma 97.26(5) _cell_volume 1156(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4223 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 26.49 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 11.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1899 _exptl_absorpt_correction_T_max 0.2649 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18040 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 30.66 _reflns_number_total 6814 _reflns_number_gt 4806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0505P)^2^+1.1052P] 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 6814 _refine_ls_number_parameters 356 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 C1 C 0.986(2) 0.399(2) 0.2930(16) 0.033(4) Uani 0.67(3) 1 d P A 1 Br1 Br 0.7695(16) 0.3710(8) 0.2006(7) 0.0360(6) Uani 0.67(3) 1 d P A 1 Br2 Br 0.9933(6) 0.2736(3) 0.3945(3) 0.0478(7) Uani 0.67(3) 1 d P A 1 Br3 Br 1.1569(6) 0.3641(9) 0.2108(5) 0.0412(10) Uani 0.67(3) 1 d P A 1 Br4 Br 1.0433(5) 0.5682(4) 0.3521(4) 0.0396(8) Uani 0.67(3) 1 d P A 1 C1B C 1.012(4) 0.386(3) 0.283(3) 0.017(5) Uani 0.33(3) 1 d PU A 2 Br1B Br 1.013(2) 0.2629(14) 0.3790(14) 0.073(2) Uani 0.33(3) 1 d P A 2 Br2B Br 1.0538(16) 0.5582(12) 0.3572(10) 0.067(3) Uani 0.33(3) 1 d P A 2 Br3B Br 1.1579(13) 0.3733(18) 0.2148(10) 0.0383(18) Uani 0.33(3) 1 d P A 2 Br4B Br 0.787(4) 0.3778(19) 0.1978(16) 0.045(4) Uani 0.33(3) 1 d P A 2 Br5 Br 0.10592(7) 0.88663(5) 0.39740(4) 0.04731(15) Uani 1 1 d . . . Cu1 Cu 0.0000 1.0000 0.5000 0.0398(2) Uani 1 2 d S . . Br6 Br 0.39041(7) 0.31646(8) 0.05051(5) 0.0694(2) Uani 1 1 d . . . Cu2 Cu 0.5000 0.5000 0.0000 0.0656(3) Uani 1 2 d S . . C2A C 0.4509(8) 0.9890(6) 0.2631(5) 0.0326(13) Uani 0.754(6) 1 d P B 1 H2A1 H 0.3405 0.9659 0.2783 0.039 Uiso 0.754(6) 1 calc PR B 1 H2A2 H 0.4343 1.0438 0.2055 0.039 Uiso 0.754(6) 1 calc PR B 1 C3A C 0.5668(8) 1.0672(7) 0.3529(5) 0.0434(16) Uani 0.754(6) 1 d P B 1 H3A1 H 0.6798 1.0872 0.3405 0.052 Uiso 0.754(6) 1 calc PR B 1 H3A2 H 0.5766 1.0167 0.4128 0.052 Uiso 0.754(6) 1 calc PR B 1 C4A C 0.499(2) 1.1939(15) 0.3725(12) 0.045(3) Uani 0.754(6) 1 d P B 1 H4A1 H 0.4831 1.2416 0.3118 0.067 Uiso 0.754(6) 1 calc PR B 1 H4A2 H 0.5785 1.2461 0.4278 0.067 Uiso 0.754(6) 1 calc PR B 1 H4A3 H 0.3908 1.1740 0.3901 0.067 Uiso 0.754(6) 1 calc PR B 1 C5A C 0.5301(8) 0.7793(6) 0.3171(5) 0.0327(13) Uani 0.754(6) 1 d P B 1 H5A1 H 0.6219 0.8214 0.3730 0.039 Uiso 0.754(6) 1 calc PR B 1 H5A2 H 0.4263 0.7710 0.3414 0.039 Uiso 0.754(6) 1 calc PR B 1 C6A C 0.5669(9) 0.6466(6) 0.2963(5) 0.0407(15) Uani 0.754(6) 1 d P B 1 H6A1 H 0.4745 0.6013 0.2423 0.049 Uiso 0.754(6) 1 calc PR B 1 H6A2 H 0.6710 0.6525 0.2724 0.049 Uiso 0.754(6) 1 calc PR B 1 C7A C 0.587(2) 0.572(2) 0.3852(14) 0.051(4) Uani 0.754(6) 1 d P B 1 H7A1 H 0.6796 0.6159 0.4384 0.076 Uiso 0.754(6) 1 calc PR B 1 H7A2 H 0.6103 0.4867 0.3683 0.076 Uiso 0.754(6) 1 calc PR B 1 H7A3 H 0.4831 0.5649 0.4084 0.076 Uiso 0.754(6) 1 calc PR B 1 C8A C 0.3814(7) 0.8025(6) 0.1405(4) 0.0333(13) Uani 0.754(6) 1 d P B 1 H8A1 H 0.3664 0.8631 0.0868 0.040 Uiso 0.754(6) 1 calc PR B 1 H8A2 H 0.4287 0.7292 0.1163 0.040 Uiso 0.754(6) 1 calc PR B 1 C9A C 0.2098(9) 0.7528(8) 0.1562(5) 0.0464(17) Uani 0.754(6) 1 d P B 1 H9A1 H 0.2256 0.6997 0.2148 0.056 Uiso 0.754(6) 1 calc PR B 1 H9A2 H 0.1572 0.8271 0.1731 0.056 Uiso 0.754(6) 1 calc PR B 1 C10A C 0.095(2) 0.6775(17) 0.0721(11) 0.057(4) Uani 0.754(6) 1 d P B 1 H10A H 0.0551 0.7339 0.0191 0.085 Uiso 0.754(6) 1 calc PR B 1 H10B H -0.0010 0.6345 0.0942 0.085 Uiso 0.754(6) 1 calc PR B 1 H10C H 0.1522 0.6130 0.0462 0.085 Uiso 0.754(6) 1 calc PR B 1 C11A C 0.6783(7) 0.8945(6) 0.2053(5) 0.0340(13) Uani 0.754(6) 1 d P B 1 H11A H 0.7655 0.9241 0.2674 0.041 Uiso 0.754(6) 1 calc PR B 1 H11B H 0.7044 0.8123 0.1800 0.041 Uiso 0.754(6) 1 calc PR B 1 C12A C 0.6898(10) 0.9919(7) 0.1279(7) 0.0462(17) Uani 0.754(6) 1 d P B 1 H12A H 0.6009 0.9644 0.0662 0.055 Uiso 0.754(6) 1 calc PR B 1 H12B H 0.6691 1.0756 0.1540 0.055 Uiso 0.754(6) 1 calc PR B 1 C13A C 0.852(2) 1.0083(17) 0.1026(14) 0.077(6) Uani 0.754(6) 1 d P B 1 H13A H 0.9394 1.0430 0.1621 0.116 Uiso 0.754(6) 1 calc PR B 1 H13B H 0.8495 1.0678 0.0493 0.116 Uiso 0.754(6) 1 calc PR B 1 H13C H 0.8754 0.9252 0.0795 0.116 Uiso 0.754(6) 1 calc PR B 1 C2B C 0.524(2) 0.9800(16) 0.3165(14) 0.026(4) Uani 0.246(6) 1 d P B 2 H2B1 H 0.4730 0.9410 0.3685 0.031 Uiso 0.246(6) 1 calc PR B 2 H2B2 H 0.6453 1.0032 0.3480 0.031 Uiso 0.246(6) 1 calc PR B 2 C3B C 0.457(3) 1.0999(18) 0.2960(14) 0.037(4) Uani 0.246(6) 1 d P B 2 H3B1 H 0.3365 1.0823 0.2609 0.044 Uiso 0.246(6) 1 calc PR B 2 H3B2 H 0.5170 1.1499 0.2527 0.044 Uiso 0.246(6) 1 calc PR B 2 C4B C 0.478(7) 1.174(5) 0.394(4) 0.035(8) Uani 0.246(6) 1 d P B 2 H4B1 H 0.4335 1.1185 0.4401 0.053 Uiso 0.246(6) 1 calc PR B 2 H4B2 H 0.4176 1.2481 0.3834 0.053 Uiso 0.246(6) 1 calc PR B 2 H4B3 H 0.5975 1.2029 0.4228 0.053 Uiso 0.246(6) 1 calc PR B 2 C5B C 0.595(2) 0.7604(18) 0.2758(13) 0.032(4) Uani 0.246(6) 1 d P B 2 H5B1 H 0.5946 0.6968 0.2210 0.039 Uiso 0.246(6) 1 calc PR B 2 H5B2 H 0.7132 0.7931 0.3092 0.039 Uiso 0.246(6) 1 calc PR B 2 C6B C 0.513(3) 0.696(2) 0.3499(15) 0.042(5) Uani 0.246(6) 1 d P B 2 H6B1 H 0.5223 0.7617 0.4053 0.051 Uiso 0.246(6) 1 calc PR B 2 H6B2 H 0.3920 0.6763 0.3166 0.051 Uiso 0.246(6) 1 calc PR B 2 C7B C 0.562(6) 0.580(5) 0.397(4) 0.029(7) Uani 0.246(6) 1 d PU B 2 H7B1 H 0.5991 0.5263 0.3492 0.044 Uiso 0.246(6) 1 calc PR B 2 H7B2 H 0.4664 0.5329 0.4161 0.044 Uiso 0.246(6) 1 calc PR B 2 H7B3 H 0.6541 0.6040 0.4566 0.044 Uiso 0.246(6) 1 calc PR B 2 C8B C 0.3173(18) 0.8364(17) 0.1889(11) 0.025(3) Uani 0.246(6) 1 d P B 2 H8B1 H 0.2625 0.8218 0.2449 0.030 Uiso 0.246(6) 1 calc PR B 2 H8B2 H 0.2744 0.9105 0.1541 0.030 Uiso 0.246(6) 1 calc PR B 2 C9B C 0.269(2) 0.7174(18) 0.1152(15) 0.035(4) Uani 0.246(6) 1 d P B 2 H9B1 H 0.3466 0.7260 0.0702 0.041 Uiso 0.246(6) 1 calc PR B 2 H9B2 H 0.2956 0.6430 0.1551 0.041 Uiso 0.246(6) 1 calc PR B 2 C10B C 0.106(4) 0.684(3) 0.053(3) 0.019(5) Uani 0.246(6) 1 d PU B 2 H10D H 0.0264 0.7226 0.0829 0.028 Uiso 0.246(6) 1 calc PR B 2 H10E H 0.0773 0.5901 0.0476 0.028 Uiso 0.246(6) 1 calc PR B 2 H10F H 0.1024 0.7147 -0.0134 0.028 Uiso 0.246(6) 1 calc PR B 2 C11B C 0.587(2) 0.9304(18) 0.1520(12) 0.031(4) Uani 0.246(6) 1 d P B 2 H11C H 0.5583 0.8687 0.0924 0.037 Uiso 0.246(6) 1 calc PR B 2 H11D H 0.5325 1.0069 0.1318 0.037 Uiso 0.246(6) 1 calc PR B 2 C12B C 0.770(3) 0.970(2) 0.177(2) 0.047(5) Uani 0.246(6) 1 d P B 2 H12C H 0.7914 1.0372 0.2325 0.056 Uiso 0.246(6) 1 calc PR B 2 H12D H 0.8184 0.8952 0.2070 0.056 Uiso 0.246(6) 1 calc PR B 2 C13B C 0.873(5) 1.015(5) 0.116(4) 0.061(14) Uani 0.246(6) 1 d P B 2 H13D H 0.8898 0.9436 0.0737 0.091 Uiso 0.246(6) 1 calc PR B 2 H13E H 0.9813 1.0555 0.1576 0.091 Uiso 0.246(6) 1 calc PR B 2 H13F H 0.8203 1.0785 0.0731 0.091 Uiso 0.246(6) 1 calc PR B 2 N1 N 0.5086(4) 0.8695(3) 0.2321(3) 0.0289(7) Uani 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 C1 0.032(6) 0.044(7) 0.029(5) -0.001(4) 0.017(4) 0.009(4) Br1 0.0303(15) 0.0398(13) 0.0363(10) -0.0012(8) 0.0071(10) 0.0017(12) Br2 0.0607(11) 0.0450(15) 0.0344(8) 0.0116(9) 0.0100(6) -0.0045(8) Br3 0.0392(14) 0.044(2) 0.0382(13) -0.0036(9) 0.0035(12) 0.0098(11) Br4 0.0409(11) 0.0340(12) 0.0444(11) -0.0053(8) 0.0164(7) -0.0025(7) C1B 0.018(8) 0.014(7) 0.019(8) -0.001(5) 0.007(6) 0.000(6) Br1B 0.058(3) 0.100(4) 0.048(4) 0.042(3) -0.002(3) -0.022(3) Br2B 0.067(4) 0.074(5) 0.054(4) -0.027(3) 0.022(3) -0.016(3) Br3B 0.035(3) 0.035(2) 0.048(4) 0.001(2) 0.017(3) 0.0021(17) Br4B 0.036(6) 0.055(5) 0.041(2) 0.0000(18) 0.009(2) 0.000(2) Br5 0.0588(3) 0.0467(3) 0.0421(3) 0.0026(2) 0.0190(2) 0.0161(2) Cu1 0.0432(4) 0.0420(5) 0.0349(4) -0.0003(3) 0.0092(3) 0.0099(4) Br6 0.0398(3) 0.1082(6) 0.0576(4) -0.0287(3) 0.0097(2) 0.0137(3) Cu2 0.0405(5) 0.0984(9) 0.0542(6) -0.0319(6) 0.0066(4) 0.0160(5) C2A 0.031(3) 0.033(3) 0.033(3) 0.000(2) 0.002(3) 0.011(2) C3A 0.038(3) 0.039(4) 0.048(4) -0.003(3) 0.001(3) 0.004(3) C4A 0.057(7) 0.031(7) 0.048(8) 0.002(5) 0.019(5) 0.004(5) C5A 0.033(3) 0.031(3) 0.029(3) 0.007(3) -0.001(2) 0.003(2) C6A 0.049(4) 0.030(3) 0.045(4) 0.008(3) 0.011(3) 0.012(3) C7A 0.054(8) 0.047(6) 0.058(7) 0.008(5) 0.022(5) 0.017(5) C8A 0.035(3) 0.038(3) 0.024(3) -0.001(2) 0.001(2) 0.005(2) C9A 0.037(4) 0.062(5) 0.036(3) -0.007(3) 0.007(3) -0.002(3) C10A 0.057(7) 0.070(8) 0.034(7) 0.011(5) 0.001(5) -0.010(5) C11A 0.029(3) 0.035(3) 0.037(3) -0.004(3) 0.009(3) 0.000(2) C12A 0.035(4) 0.045(4) 0.066(5) 0.018(4) 0.022(3) 0.009(3) C13A 0.078(10) 0.074(9) 0.090(11) 0.015(8) 0.057(9) -0.021(7) C2B 0.024(8) 0.029(9) 0.026(9) 0.006(7) 0.011(7) -0.002(7) C3B 0.043(10) 0.033(10) 0.032(9) -0.003(7) 0.004(8) 0.012(8) C4B 0.044(16) 0.025(14) 0.038(18) 0.016(11) 0.014(13) -0.004(10) C5B 0.035(9) 0.043(11) 0.029(8) 0.005(7) 0.027(8) 0.012(8) C6B 0.045(11) 0.059(14) 0.032(10) 0.001(10) 0.020(8) 0.019(10) C7B 0.032(10) 0.028(10) 0.030(10) 0.007(8) 0.004(8) 0.015(8) C8B 0.018(7) 0.039(9) 0.018(7) -0.002(6) 0.006(6) -0.001(6) C9B 0.023(8) 0.040(10) 0.044(10) -0.007(8) 0.013(8) 0.009(7) C10B 0.016(8) 0.015(7) 0.016(8) 0.006(6) -0.011(6) -0.006(6) C11B 0.036(9) 0.038(10) 0.020(8) 0.001(7) 0.009(7) 0.000(8) C12B 0.042(13) 0.032(11) 0.064(16) -0.005(10) 0.012(12) 0.005(10) C13B 0.028(13) 0.07(2) 0.07(2) -0.037(19) -0.010(14) 0.018(14) N1 0.0251(16) 0.0318(18) 0.0278(17) 0.0016(14) 0.0030(13) 0.0032(14) _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 C1 Br4 1.89(2) . ? C1 Br1 1.92(2) . ? C1 Br2 1.95(2) . ? C1 Br3 2.07(2) . ? C1B Br3B 1.71(4) . ? C1B Br1B 1.88(4) . ? C1B Br4B 1.95(4) . ? C1B Br2B 2.00(3) . ? Br5 Cu1 2.219(3) . ? Cu1 Br5 2.219(3) 2_576 ? Br6 Cu2 2.236(3) . ? Cu2 Br6 2.236(3) 2_665 ? C2A N1 1.485(7) . ? C2A C3A 1.514(9) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.55(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C5A C6A 1.500(9) . ? C5A N1 1.524(7) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.46(2) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8A C9A 1.521(9) . ? C8A N1 1.523(7) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.448(17) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A C12A 1.515(10) . ? C11A N1 1.533(7) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.458(17) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C2B C3B 1.46(3) . ? C2B N1 1.585(18) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.49(6) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B H4B1 0.9800 . ? C4B H4B2 0.9800 . ? C4B H4B3 0.9800 . ? C5B C6B 1.49(3) . ? C5B N1 1.500(18) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.46(6) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B H7B1 0.9800 . ? C7B H7B2 0.9800 . ? C7B H7B3 0.9800 . ? C8B C9B 1.53(2) . ? C8B N1 1.546(15) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.41(3) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B C12B 1.48(3) . ? C11B N1 1.529(17) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.39(6) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 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 Br4 C1 Br1 113.1(11) . . ? Br4 C1 Br2 111.4(10) . . ? Br1 C1 Br2 109.1(10) . . ? Br4 C1 Br3 108.8(10) . . ? Br1 C1 Br3 106.3(10) . . ? Br2 C1 Br3 107.9(9) . . ? Br3B C1B Br1B 113.3(19) . . ? Br3B C1B Br4B 112(2) . . ? Br1B C1B Br4B 109.2(17) . . ? Br3B C1B Br2B 110.8(17) . . ? Br1B C1B Br2B 107.0(17) . . ? Br4B C1B Br2B 104.0(16) . . ? Br5 Cu1 Br5 180.0 . 2_576 ? Br6 Cu2 Br6 180.00(3) . 2_665 ? N1 C2A C3A 115.7(5) . . ? N1 C2A H2A1 108.4 . . ? C3A C2A H2A1 108.4 . . ? N1 C2A H2A2 108.4 . . ? C3A C2A H2A2 108.4 . . ? H2A1 C2A H2A2 107.4 . . ? C2A C3A C4A 110.5(9) . . ? C2A C3A H3A1 109.6 . . ? C4A C3A H3A1 109.6 . . ? C2A C3A H3A2 109.6 . . ? C4A C3A H3A2 109.6 . . ? H3A1 C3A H3A2 108.1 . . ? C6A C5A N1 118.6(5) . . ? C6A C5A H5A1 107.7 . . ? N1 C5A H5A1 107.7 . . ? C6A C5A H5A2 107.7 . . ? N1 C5A H5A2 107.7 . . ? H5A1 C5A H5A2 107.1 . . ? C7A C6A C5A 112.2(10) . . ? C7A C6A H6A1 109.2 . . ? C5A C6A H6A1 109.2 . . ? C7A C6A H6A2 109.2 . . ? C5A C6A H6A2 109.2 . . ? H6A1 C6A H6A2 107.9 . . ? C9A C8A N1 116.0(5) . . ? C9A C8A H8A1 108.3 . . ? N1 C8A H8A1 108.3 . . ? C9A C8A H8A2 108.3 . . ? N1 C8A H8A2 108.3 . . ? H8A1 C8A H8A2 107.4 . . ? C10A C9A C8A 115.9(8) . . ? C10A C9A H9A1 108.3 . . ? C8A C9A H9A1 108.3 . . ? C10A C9A H9A2 108.3 . . ? C8A C9A H9A2 108.3 . . ? H9A1 C9A H9A2 107.4 . . ? C12A C11A N1 115.5(5) . . ? C12A C11A H11A 108.4 . . ? N1 C11A H11A 108.4 . . ? C12A C11A H11B 108.4 . . ? N1 C11A H11B 108.4 . . ? H11A C11A H11B 107.5 . . ? C13A C12A C11A 113.0(9) . . ? C13A C12A H12A 109.0 . . ? C11A C12A H12A 109.0 . . ? C13A C12A H12B 109.0 . . ? C11A C12A H12B 109.0 . . ? H12A C12A H12B 107.8 . . ? C3B C2B N1 122.9(15) . . ? C3B C2B H2B1 106.6 . . ? N1 C2B H2B1 106.6 . . ? C3B C2B H2B2 106.6 . . ? N1 C2B H2B2 106.6 . . ? H2B1 C2B H2B2 106.6 . . ? C2B C3B C4B 108(2) . . ? C2B C3B H3B1 110.1 . . ? C4B C3B H3B1 110.1 . . ? C2B C3B H3B2 110.1 . . ? C4B C3B H3B2 110.1 . . ? H3B1 C3B H3B2 108.5 . . ? C3B C4B H4B1 109.5 . . ? C3B C4B H4B2 109.5 . . ? H4B1 C4B H4B2 109.5 . . ? C3B C4B H4B3 109.5 . . ? H4B1 C4B H4B3 109.5 . . ? H4B2 C4B H4B3 109.5 . . ? C6B C5B N1 112.1(14) . . ? C6B C5B H5B1 109.2 . . ? N1 C5B H5B1 109.2 . . ? C6B C5B H5B2 109.2 . . ? N1 C5B H5B2 109.2 . . ? H5B1 C5B H5B2 107.9 . . ? C7B C6B C5B 123(2) . . ? C7B C6B H6B1 106.5 . . ? C5B C6B H6B1 106.5 . . ? C7B C6B H6B2 106.5 . . ? C5B C6B H6B2 106.5 . . ? H6B1 C6B H6B2 106.5 . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C9B C8B N1 113.0(12) . . ? C9B C8B H8B1 109.0 . . ? N1 C8B H8B1 109.0 . . ? C9B C8B H8B2 109.0 . . ? N1 C8B H8B2 109.0 . . ? H8B1 C8B H8B2 107.8 . . ? C10B C9B C8B 122(2) . . ? C10B C9B H9B1 106.7 . . ? C8B C9B H9B1 106.7 . . ? C10B C9B H9B2 106.7 . . ? C8B C9B H9B2 106.7 . . ? H9B1 C9B H9B2 106.6 . . ? C9B C10B H10D 109.5 . . ? C9B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C12B C11B N1 118.4(16) . . ? C12B C11B H11C 107.7 . . ? N1 C11B H11C 107.7 . . ? C12B C11B H11D 107.7 . . ? N1 C11B H11D 107.7 . . ? H11C C11B H11D 107.1 . . ? C13B C12B C11B 130(3) . . ? C13B C12B H12C 104.8 . . ? C11B C12B H12C 104.8 . . ? C13B C12B H12D 104.8 . . ? C11B C12B H12D 104.8 . . ? H12C C12B H12D 105.8 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C2A N1 C5B 141.0(8) . . ? C2A N1 C8A 109.8(4) . . ? C5B N1 C8A 101.7(8) . . ? C2A N1 C5A 110.5(4) . . ? C5B N1 C5A 34.8(6) . . ? C8A N1 C5A 109.3(4) . . ? C2A N1 C11B 94.8(8) . . ? C5B N1 C11B 112.0(10) . . ? C8A N1 C11B 82.3(7) . . ? C5A N1 C11B 145.3(8) . . ? C2A N1 C11A 112.7(4) . . ? C5B N1 C11A 77.2(7) . . ? C8A N1 C11A 107.8(4) . . ? C5A N1 C11A 106.5(4) . . ? C11B N1 C11A 39.7(7) . . ? C2A N1 C8B 79.4(7) . . ? C5B N1 C8B 115.1(10) . . ? C8A N1 C8B 39.0(6) . . ? C5A N1 C8B 99.1(7) . . ? C11B N1 C8B 108.9(9) . . ? C11A N1 C8B 144.6(7) . . ? C2A N1 C2B 32.1(7) . . ? C5B N1 C2B 110.4(10) . . ? C8A N1 C2B 139.8(8) . . ? C5A N1 C2B 86.0(7) . . ? C11B N1 C2B 106.3(9) . . ? C11A N1 C2B 102.4(7) . . ? C8B N1 C2B 103.4(9) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 30.66 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 1.769 _refine_diff_density_min -0.765 _refine_diff_density_rms 0.131 # Attachment 'Compound_II.cif' data_II _database_code_depnum_ccdc_archive 'CCDC 644448' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H28 N, 2(C Br4), Br2 Cu' _chemical_formula_sum 'C7 H14 Br5 Cu0.50 N0.50' _chemical_formula_weight 536.51 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/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 12.022(4) _cell_length_b 12.703(4) _cell_length_c 19.990(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.994(8) _cell_angle_gamma 90.00 _cell_volume 2974.7(17) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2767 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 14.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1466 _exptl_absorpt_correction_T_max 0.1847 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22201 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.63 _reflns_number_total 4465 _reflns_number_gt 2416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0000P)^2^+2.2278P] 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 4465 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C1 C 0.7506(4) -0.0049(4) 0.4983(2) 0.0364(11) Uani 1 1 d . . . Br1 Br 0.67188(4) 0.07543(4) 0.55510(2) 0.03792(15) Uani 1 1 d . . . Br2 Br 0.64197(4) -0.09046(4) 0.43442(3) 0.04499(16) Uani 1 1 d . . . Br3 Br 0.82522(5) 0.08945(4) 0.44657(3) 0.04922(17) Uani 1 1 d . . . Br4 Br 0.86082(4) -0.09620(4) 0.55557(3) 0.04969(17) Uani 1 1 d . . . Br5 Br 0.93391(5) 0.25432(4) 0.34495(3) 0.04568(16) Uani 1 1 d . . . Cu1 Cu 1.0000 0.25775(6) 0.2500 0.0359(2) Uani 1 2 d S . . N1 N 1.0000 0.1315(4) 0.7500 0.0476(17) Uani 1 2 d S . . C2 C 0.9659(11) 0.1743(8) 0.6855(5) 0.034(3) Uani 0.482(9) 1 d P A 1 H2A H 0.8861 0.1990 0.6790 0.041 Uiso 0.482(9) 1 calc PR A 1 H2B H 0.9675 0.1187 0.6510 0.041 Uiso 0.482(9) 1 calc PR A 1 C3 C 1.0394(13) 0.2646(9) 0.6729(8) 0.047(4) Uani 0.482(9) 1 d P A 1 H3A H 1.1211 0.2470 0.6902 0.057 Uiso 0.482(9) 1 calc PR A 1 H3B H 1.0220 0.3282 0.6972 0.057 Uiso 0.482(9) 1 calc PR A 1 C4 C 1.015(2) 0.285(2) 0.5962(9) 0.061(6) Uani 0.482(9) 1 d P A 1 H4A H 1.0417 0.2250 0.5732 0.092 Uiso 0.482(9) 1 calc PR A 1 H4B H 1.0545 0.3489 0.5873 0.092 Uiso 0.482(9) 1 calc PR A 1 H4C H 0.9325 0.2937 0.5787 0.092 Uiso 0.482(9) 1 calc PR A 1 C5 C 0.9080(10) 0.0398(9) 0.7595(6) 0.033(3) Uani 0.482(9) 1 d P A 1 H5A H 0.9062 -0.0129 0.7228 0.040 Uiso 0.482(9) 1 calc PR A 1 H5B H 0.9394 0.0040 0.8036 0.040 Uiso 0.482(9) 1 calc PR A 1 C6 C 0.7863(10) 0.0686(9) 0.7586(5) 0.038(3) Uani 0.482(9) 1 d P A 1 H6A H 0.7834 0.1096 0.8003 0.045 Uiso 0.482(9) 1 calc PR A 1 H6B H 0.7550 0.1129 0.7180 0.045 Uiso 0.482(9) 1 calc PR A 1 C7 C 0.720(3) -0.023(3) 0.7563(9) 0.053(6) Uani 0.482(9) 1 d P A 1 H7A H 0.6393 -0.0043 0.7458 0.080 Uiso 0.482(9) 1 calc PR A 1 H7B H 0.7402 -0.0586 0.8009 0.080 Uiso 0.482(9) 1 calc PR A 1 H7C H 0.7358 -0.0702 0.7207 0.080 Uiso 0.482(9) 1 calc PR A 1 C8 C 1.0255(12) 0.2201(9) 0.6928(6) 0.040(3) Uani 0.518(9) 1 d P A 2 H8A H 0.9780 0.2829 0.6957 0.048 Uiso 0.518(9) 1 calc PR A 2 H8B H 1.1063 0.2423 0.7076 0.048 Uiso 0.518(9) 1 calc PR A 2 C9 C 1.0050(9) 0.1885(7) 0.6186(5) 0.039(3) Uani 0.518(9) 1 d P A 2 H9A H 0.9226 0.1758 0.6000 0.046 Uiso 0.518(9) 1 calc PR A 2 H9B H 1.0470 0.1229 0.6140 0.046 Uiso 0.518(9) 1 calc PR A 2 C10 C 1.047(2) 0.2779(17) 0.5790(11) 0.056(5) Uani 0.518(9) 1 d P A 2 H10A H 1.0139 0.3448 0.5897 0.084 Uiso 0.518(9) 1 calc PR A 2 H10B H 1.0229 0.2642 0.5296 0.084 Uiso 0.518(9) 1 calc PR A 2 H10C H 1.1303 0.2820 0.5923 0.084 Uiso 0.518(9) 1 calc PR A 2 C11 C 0.8886(9) 0.0893(8) 0.7220(6) 0.042(3) Uani 0.518(9) 1 d P A 2 H11A H 0.8897 0.0484 0.6800 0.051 Uiso 0.518(9) 1 calc PR A 2 H11B H 0.8330 0.1475 0.7094 0.051 Uiso 0.518(9) 1 calc PR A 2 C12 C 0.8535(12) 0.0196(10) 0.7740(6) 0.048(3) Uani 0.518(9) 1 d P A 2 H12A H 0.8464 0.0609 0.8148 0.057 Uiso 0.518(9) 1 calc PR A 2 H12B H 0.9108 -0.0366 0.7888 0.057 Uiso 0.518(9) 1 calc PR A 2 C13 C 0.725(3) -0.034(2) 0.7353(9) 0.045(5) Uani 0.518(9) 1 d P A 2 H13A H 0.6680 0.0225 0.7239 0.068 Uiso 0.518(9) 1 calc PR A 2 H13B H 0.7014 -0.0839 0.7665 0.068 Uiso 0.518(9) 1 calc PR A 2 H13C H 0.7320 -0.0699 0.6932 0.068 Uiso 0.518(9) 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 C1 0.025(2) 0.037(3) 0.049(3) -0.003(2) 0.013(2) -0.006(2) Br1 0.0337(3) 0.0406(3) 0.0423(3) 0.0002(2) 0.0145(2) 0.0077(2) Br2 0.0369(3) 0.0433(3) 0.0572(3) -0.0116(2) 0.0156(3) -0.0108(2) Br3 0.0480(4) 0.0507(4) 0.0564(3) -0.0087(3) 0.0274(3) -0.0197(3) Br4 0.0346(3) 0.0412(3) 0.0731(4) -0.0053(3) 0.0116(3) 0.0091(2) Br5 0.0587(4) 0.0428(3) 0.0418(3) -0.0067(2) 0.0245(3) -0.0062(3) Cu1 0.0407(5) 0.0327(5) 0.0370(5) 0.000 0.0147(4) 0.000 N1 0.048(4) 0.019(3) 0.060(4) 0.000 -0.020(3) 0.000 C2 0.056(8) 0.021(6) 0.025(5) -0.002(4) 0.008(5) -0.002(5) C3 0.054(8) 0.031(8) 0.056(9) 0.001(6) 0.011(7) -0.005(6) C4 0.072(15) 0.078(13) 0.030(9) 0.015(8) 0.001(8) -0.041(12) C5 0.041(8) 0.030(6) 0.027(6) 0.012(5) 0.004(5) -0.001(5) C6 0.034(7) 0.042(7) 0.031(6) 0.010(5) -0.005(5) -0.003(5) C7 0.076(12) 0.069(13) 0.010(9) -0.008(9) 0.001(11) -0.021(10) C8 0.045(8) 0.020(6) 0.049(8) 0.006(5) -0.004(6) -0.008(6) C9 0.049(7) 0.027(5) 0.040(6) 0.000(4) 0.010(5) -0.009(5) C10 0.070(11) 0.047(8) 0.064(12) 0.017(8) 0.041(9) 0.003(8) C11 0.043(7) 0.034(6) 0.043(6) 0.008(5) -0.002(5) 0.006(5) C12 0.058(10) 0.044(7) 0.044(7) 0.017(5) 0.018(7) -0.004(7) C13 0.070(10) 0.045(8) 0.019(10) -0.004(9) 0.006(10) -0.024(7) _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 C1 Br1 1.925(5) . ? C1 Br3 1.931(5) . ? C1 Br4 1.931(5) . ? C1 Br2 1.941(4) . ? Br5 Cu1 2.2168(8) . ? Cu1 Br5 2.2168(8) 2_755 ? N1 C2 1.374(9) . ? N1 C2 1.374(10) 2_756 ? N1 C11 1.434(10) 2_756 ? N1 C11 1.434(10) . ? N1 C5 1.646(12) . ? N1 C5 1.646(12) 2_756 ? N1 C8 1.681(12) . ? N1 C8 1.681(12) 2_756 ? C2 C3 1.504(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.52(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.504(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.40(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.502(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.53(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.497(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.70(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 Br1 C1 Br3 109.6(2) . . ? Br1 C1 Br4 109.4(2) . . ? Br3 C1 Br4 110.5(2) . . ? Br1 C1 Br2 109.7(2) . . ? Br3 C1 Br2 108.7(2) . . ? Br4 C1 Br2 108.9(2) . . ? Br5 Cu1 Br5 177.75(5) . 2_755 ? C2 N1 C2 133.5(10) . 2_756 ? C2 N1 C11 124.7(7) . 2_756 ? C2 N1 C11 74.1(7) 2_756 2_756 ? C2 N1 C11 74.1(7) . . ? C2 N1 C11 124.7(7) 2_756 . ? C11 N1 C11 136.1(9) 2_756 . ? C2 N1 C5 108.7(7) . . ? C2 N1 C5 103.8(6) 2_756 . ? C11 N1 C5 106.4(7) 2_756 . ? C11 N1 C5 35.7(5) . . ? C2 N1 C5 103.7(6) . 2_756 ? C2 N1 C5 108.7(7) 2_756 2_756 ? C11 N1 C5 35.7(5) 2_756 2_756 ? C11 N1 C5 106.4(7) . 2_756 ? C5 N1 C5 89.9(9) . 2_756 ? C2 N1 C8 32.7(6) . . ? C2 N1 C8 108.2(7) 2_756 . ? C11 N1 C8 102.6(6) 2_756 . ? C11 N1 C8 106.4(6) . . ? C5 N1 C8 141.4(6) . . ? C5 N1 C8 99.5(6) 2_756 . ? C2 N1 C8 108.2(7) . 2_756 ? C2 N1 C8 32.7(6) 2_756 2_756 ? C11 N1 C8 106.4(6) 2_756 2_756 ? C11 N1 C8 102.6(6) . 2_756 ? C5 N1 C8 99.5(6) . 2_756 ? C5 N1 C8 141.4(6) 2_756 2_756 ? C8 N1 C8 95.9(9) . 2_756 ? N1 C2 C3 113.3(10) . . ? N1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 108.1(12) . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C6 C5 N1 120.3(9) . . ? C6 C5 H5A 107.3 . . ? N1 C5 H5A 107.3 . . ? C6 C5 H5B 107.3 . . ? N1 C5 H5B 107.3 . . ? H5A C5 H5B 106.9 . . ? C7 C6 C5 109.8(19) . . ? C7 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? C7 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C9 C8 N1 118.6(8) . . ? C9 C8 H8A 107.7 . . ? N1 C8 H8A 107.7 . . ? C9 C8 H8B 107.7 . . ? N1 C8 H8B 107.7 . . ? H8A C8 H8B 107.1 . . ? C8 C9 C10 108.2(12) . . ? C8 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? C8 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 109.6(9) . . ? N1 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N1 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 106.7(11) . . ? C11 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? C11 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.63 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.033 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.149 # Attachment 'Compound_III.cif' data_III _database_code_depnum_ccdc_archive 'CCDC 644449' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H12 N, Br3 Cu2' _chemical_formula_sum 'C4 H12 Br3 Cu2 N' _chemical_formula_weight 440.96 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 16.535(5) _cell_length_b 6.558(2) _cell_length_c 9.621(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1043.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3687 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.49 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 15.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0479 _exptl_absorpt_correction_T_max 0.1475 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7673 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 30.49 _reflns_number_total 1679 _reflns_number_gt 1452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0340P)^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 1679 _refine_ls_number_parameters 58 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0599 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 Br1 Br 0.042063(18) 0.2500 0.63103(3) 0.01988(9) Uani 1 2 d S . . Br2 Br 0.17342(2) -0.2500 0.50368(3) 0.02638(10) Uani 1 2 d S . . Br3 Br 0.10214(2) 0.2500 0.24939(3) 0.02758(10) Uani 1 2 d S . . Cu1 Cu 0.07479(2) -0.00027(4) 0.43213(3) 0.03300(10) Uani 1 1 d . . . C1 C 0.0665(2) 0.7500 1.0405(4) 0.0318(7) Uani 1 2 d S . . H1A H 0.0246 0.7205 0.9713 0.048 Uiso 0.50 1 calc PR . . H1B H 0.0564 0.8840 1.0821 0.048 Uiso 0.50 1 calc PR . . H1C H 0.0653 0.6454 1.1133 0.048 Uiso 0.50 1 calc PR . . C2 C 0.2126(2) 0.7500 1.0801(4) 0.0337(8) Uani 1 2 d S . . H2A H 0.2646 0.7163 1.0370 0.051 Uiso 0.50 1 calc PR . . H2B H 0.1997 0.6484 1.1515 0.051 Uiso 0.50 1 calc PR . . H2C H 0.2159 0.8853 1.1230 0.051 Uiso 0.50 1 calc PR . . C3 C 0.15513(19) 0.9354(3) 0.8831(3) 0.0374(6) Uani 1 1 d . . . H3A H 0.1486 1.0574 0.9408 0.056 Uiso 1 1 calc R . . H3B H 0.1131 0.9331 0.8113 0.056 Uiso 1 1 calc R . . H3C H 0.2085 0.9376 0.8389 0.056 Uiso 1 1 calc R . . N1 N 0.14783(17) 0.7500 0.9717(3) 0.0211(5) Uani 1 2 d S . . 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 Br1 0.02213(17) 0.01741(14) 0.02010(14) 0.000 -0.00119(11) 0.000 Br2 0.02316(18) 0.01979(15) 0.03618(19) 0.000 -0.00299(14) 0.000 Br3 0.0416(2) 0.01850(15) 0.02260(16) 0.000 0.00388(13) 0.000 Cu1 0.0376(2) 0.02581(16) 0.03555(19) 0.00475(11) -0.00012(15) 0.00333(12) C1 0.0236(18) 0.0321(17) 0.0396(18) 0.000 0.0031(15) 0.000 C2 0.030(2) 0.0352(18) 0.0361(18) 0.000 -0.0118(15) 0.000 C3 0.0546(19) 0.0241(11) 0.0335(12) 0.0106(10) -0.0005(12) -0.0063(12) N1 0.0258(15) 0.0180(11) 0.0196(11) 0.000 -0.0020(10) 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 Br1 Cu1 2.5785(6) . ? Br1 Cu1 2.5785(6) 7_565 ? Br1 Cu1 2.6047(7) 5_556 ? Br1 Cu1 2.6047(7) 3_556 ? Br2 Cu1 2.4115(6) 7 ? Br2 Cu1 2.4115(6) . ? Br3 Cu1 2.4473(6) 7_565 ? Br3 Cu1 2.4473(6) . ? Cu1 Br1 2.6047(7) 5_556 ? Cu1 Cu1 2.7968(9) 5_556 ? C1 N1 1.499(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.495(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.490(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? N1 C3 1.490(3) 7_575 ? 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 Cu1 Br1 Cu1 79.07(3) . 7_565 ? Cu1 Br1 Cu1 65.311(19) . 5_556 ? Cu1 Br1 Cu1 112.504(18) 7_565 5_556 ? Cu1 Br1 Cu1 112.504(18) . 3_556 ? Cu1 Br1 Cu1 65.312(19) 7_565 3_556 ? Cu1 Br1 Cu1 77.92(3) 5_556 3_556 ? Cu1 Br2 Cu1 85.55(3) 7 . ? Cu1 Br3 Cu1 84.23(3) 7_565 . ? Br2 Cu1 Br3 122.38(2) . . ? Br2 Cu1 Br1 111.25(2) . . ? Br3 Cu1 Br1 98.34(3) . . ? Br2 Cu1 Br1 98.12(2) . 5_556 ? Br3 Cu1 Br1 113.03(2) . 5_556 ? Br1 Cu1 Br1 114.688(19) . 5_556 ? Br2 Cu1 Cu1 117.75(2) . 5_556 ? Br3 Cu1 Cu1 119.87(2) . 5_556 ? Br1 Cu1 Cu1 57.797(14) . 5_556 ? Br1 Cu1 Cu1 56.891(19) 5_556 5_556 ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 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 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 N1 C3 109.4(3) 7_575 . ? C3 N1 C2 109.95(18) 7_575 . ? C3 N1 C2 109.95(18) . . ? C3 N1 C1 109.00(18) 7_575 . ? C3 N1 C1 109.00(18) . . ? C2 N1 C1 109.5(3) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.699 _refine_diff_density_min -0.938 _refine_diff_density_rms 0.254