# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Jiri Pospisil' 'Marek Necas' 'Petr Taborsky' 'Inke Jess' 'Christian Nather' _publ_contact_author_name 'Marek Necas' _publ_contact_author_email man@chemi.muni.cz data_tab1 _database_code_depnum_ccdc_archive 'CCDC 794902' #TrackingRef 'TAB1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H2 Br Cu N' _chemical_formula_weight 183.50 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 3.9006(4) _cell_length_b 6.9280(7) _cell_length_c 7.7307(8) _cell_angle_alpha 107.693(9) _cell_angle_beta 99.426(8) _cell_angle_gamma 94.527(8) _cell_volume 194.49(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 897 _cell_measurement_theta_min 3.1202 _cell_measurement_theta_max 27.3518 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 170 _exptl_absorpt_coefficient_mu 15.655 _exptl_absorpt_correction_T_min 0.25926 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.4353 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1064 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 681 _reflns_number_gt 616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction Ltd, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0749P)^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 681 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_restrained_S_all 1.204 _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 0.77913(14) 0.83901(10) 0.65087(8) 0.0175(3) Uani 1 1 d . . . Cu1 Cu 0.30204(19) 1.05443(13) 0.63630(11) 0.0205(3) Uani 1 1 d . . . N1 N 0.4248(12) 1.3188(8) 0.8503(7) 0.0151(12) Uani 1 1 d . . . C1 C 0.3151(16) 1.4935(10) 0.8371(9) 0.0173(14) Uani 1 1 d . . . H1 H 0.1848 1.4946 0.7223 0.021 Uiso 1 1 calc R . . C2 C 0.6133(15) 1.3295(10) 1.0147(9) 0.0180(14) Uani 1 1 d . . . H2 H 0.7009 1.2101 1.0294 0.022 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 Br1 0.0136(4) 0.0227(5) 0.0194(5) 0.0113(3) 0.0030(3) 0.0038(3) Cu1 0.0207(5) 0.0197(5) 0.0181(5) 0.0036(4) 0.0008(4) 0.0018(4) N1 0.015(3) 0.015(3) 0.014(3) 0.005(2) 0.002(2) 0.000(2) C1 0.018(3) 0.022(4) 0.015(3) 0.013(3) 0.002(3) 0.001(3) C2 0.019(3) 0.019(4) 0.019(3) 0.010(3) 0.002(3) 0.004(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 Br1 Cu1 2.4692(10) 1_655 ? Br1 Cu1 2.4850(10) . ? Br1 Cu1 2.5252(11) 2_676 ? Cu1 N1 2.020(5) . ? Cu1 Br1 2.4692(10) 1_455 ? Cu1 Br1 2.5252(11) 2_676 ? Cu1 Cu1 2.7710(16) 2_676 ? Cu1 Cu1 2.7729(15) 2_576 ? N1 C2 1.338(8) . ? N1 C1 1.342(9) . ? C1 C2 1.372(9) 2_687 ? C2 C1 1.372(9) 2_687 ? 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 103.87(4) 1_655 . ? Cu1 Br1 Cu1 67.44(3) 1_655 2_676 ? Cu1 Br1 Cu1 67.15(3) . 2_676 ? N1 Cu1 Br1 112.89(15) . 1_455 ? N1 Cu1 Br1 109.71(15) . . ? Br1 Cu1 Br1 103.87(4) 1_455 . ? N1 Cu1 Br1 105.13(17) . 2_676 ? Br1 Cu1 Br1 112.56(3) 1_455 2_676 ? Br1 Cu1 Br1 112.85(3) . 2_676 ? N1 Cu1 Cu1 122.70(16) . 2_676 ? Br1 Cu1 Cu1 124.38(5) 1_455 2_676 ? Br1 Cu1 Cu1 57.12(3) . 2_676 ? Br1 Cu1 Cu1 55.73(3) 2_676 2_676 ? N1 Cu1 Cu1 125.73(15) . 2_576 ? Br1 Cu1 Cu1 57.24(3) 1_455 2_576 ? Br1 Cu1 Cu1 124.55(5) . 2_576 ? Br1 Cu1 Cu1 55.32(3) 2_676 2_576 ? Cu1 Cu1 Cu1 89.43(5) 2_676 2_576 ? C2 N1 C1 116.0(5) . . ? C2 N1 Cu1 122.2(5) . . ? C1 N1 Cu1 121.8(4) . . ? N1 C1 C2 121.6(6) . 2_687 ? N1 C2 C1 122.4(6) . 2_687 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.262 _refine_diff_density_min -1.147 _refine_diff_density_rms 0.255