# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_0491 _database_code_depnum_ccdc_archive 'CCDC 693833' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common 'Bis(4-chloro-anilinium) pentabromocadmate' _chemical_melting_point ? _chemical_formula_moiety 'Br5 Cd, 3(C6 H7 Cl N)' _chemical_formula_sum 'C18 H21 Br5 Cd Cl3 N3' _chemical_formula_weight 897.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 15.033(2) _cell_length_b 8.0189(12) _cell_length_c 23.103(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.649(8) _cell_angle_gamma 90.00 _cell_volume 2745.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 4.85 _cell_measurement_theta_max 13.35 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 8.376 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.257 _exptl_absorpt_correction_T_max 0.338 _exptl_absorpt_process_details XSCANS(Bruker,1996) _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 'Bruker P4' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6794 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0967 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5305 _reflns_number_gt 2960 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Bruker,1996)' _computing_cell_refinement 'XSCANS (Bruker,1996)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_structure_solution 'SIR97 (Altomare,1999)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _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^)+(0.0354P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00323(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5305 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1254 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.2481(6) 0.4730(11) 0.4686(4) 0.044(2) Uani 1 1 d . . . C2 C 0.2219(7) 0.5191(13) 0.4115(4) 0.058(3) Uani 1 1 d . . . H2D H 0.2638 0.5623 0.3901 0.070 Uiso 1 1 calc R . . C3 C 0.1330(7) 0.5016(13) 0.3856(4) 0.064(3) Uani 1 1 d . . . H3D H 0.1137 0.5328 0.3467 0.077 Uiso 1 1 calc R . . C4 C 0.0734(6) 0.4363(12) 0.4190(4) 0.053(3) Uani 1 1 d . . . C5 C 0.0997(7) 0.3863(14) 0.4746(4) 0.069(3) Uani 1 1 d . . . H5A H 0.0585 0.3383 0.4954 0.082 Uiso 1 1 calc R . . C6 C 0.1894(7) 0.4070(15) 0.5007(4) 0.062(3) Uani 1 1 d . . . C7 C 0.2435(6) -0.0015(12) 0.2941(4) 0.042(2) Uani 1 1 d . . . C8 C 0.1955(6) 0.0898(12) 0.3267(4) 0.051(3) Uani 1 1 d . . . H8A H 0.2221 0.1785 0.3491 0.061 Uiso 1 1 calc R . . C9 C 0.1053(7) 0.0500(12) 0.3265(4) 0.063(3) Uani 1 1 d . . . H9A H 0.0704 0.1138 0.3478 0.076 Uiso 1 1 calc R . . C10 C 0.0687(6) -0.0840(13) 0.2946(4) 0.053(3) Uani 1 1 d . . . C11 C 0.1175(7) -0.1768(13) 0.2629(4) 0.066(3) Uani 1 1 d . . . H11A H 0.0912 -0.2673 0.2414 0.079 Uiso 1 1 calc R . . C12 C 0.2068(6) -0.1373(12) 0.2624(4) 0.052(3) Uani 1 1 d . . . H12A H 0.2414 -0.2013 0.2410 0.062 Uiso 1 1 calc R . . C13 C 0.3136(6) -0.0018(11) 0.5941(4) 0.042(2) Uani 1 1 d . . . C14 C 0.3265(6) -0.0194(13) 0.5368(4) 0.048(3) Uani 1 1 d . . . C15 C 0.2544(6) -0.0565(12) 0.4951(4) 0.052(3) Uani 1 1 d . . . H15A H 0.2615 -0.0696 0.4562 0.063 Uiso 1 1 calc R . . C16 C 0.1711(6) -0.0745(12) 0.5108(4) 0.050(3) Uani 1 1 d . . . C17 C 0.1580(6) -0.0519(13) 0.5672(4) 0.066(3) Uani 1 1 d . . . H17A H 0.1003 -0.0590 0.5766 0.080 Uiso 1 1 calc R . . C18 C 0.2303(6) -0.0188(13) 0.6097(4) 0.060(3) Uani 1 1 d . . . H18A H 0.2231 -0.0079 0.6487 0.072 Uiso 1 1 calc R . . N1 N 0.3444(5) 0.4919(9) 0.4954(3) 0.058(2) Uani 1 1 d . . . H1A H 0.3499 0.4857 0.5343 0.087 Uiso 1 1 calc R . . H1B H 0.3646 0.5903 0.4854 0.087 Uiso 1 1 calc R . . H1C H 0.3766 0.4109 0.4825 0.087 Uiso 1 1 calc R . . N2 N 0.3376(5) 0.0378(9) 0.2926(3) 0.055(2) Uani 1 1 d . . . H2A H 0.3412 0.1379 0.2765 0.083 Uiso 1 1 calc R . . H2B H 0.3606 -0.0386 0.2714 0.083 Uiso 1 1 calc R . . H2C H 0.3685 0.0382 0.3290 0.083 Uiso 1 1 calc R . . N3 N 0.3919(4) 0.0352(8) 0.6403(3) 0.047(2) Uani 1 1 d . . . H3A H 0.3817 0.1294 0.6585 0.071 Uiso 1 1 calc R . . H3B H 0.4412 0.0465 0.6241 0.071 Uiso 1 1 calc R . . H3C H 0.3997 -0.0481 0.6661 0.071 Uiso 1 1 calc R . . Cl1 Cl -0.04000(19) 0.4199(4) 0.38679(13) 0.0937(11) Uani 1 1 d . . . Cl2 Cl -0.04426(19) -0.1337(4) 0.29575(15) 0.0942(11) Uani 1 1 d . . . Cl3 Cl 0.07777(17) -0.1230(4) 0.45715(11) 0.0760(9) Uani 1 1 d . . . Br1 Br 0.56528(6) 0.23982(12) 0.59430(4) 0.0495(3) Uani 1 1 d . . . Br2 Br 0.69803(6) 0.55507(12) 0.72703(4) 0.0436(3) Uani 1 1 d . . . Br3 Br 0.54176(7) 0.74053(12) 0.58534(4) 0.0503(3) Uani 1 1 d . . . Br4 Br 0.34850(6) 0.45292(13) 0.63868(4) 0.0526(3) Uani 1 1 d . . . Br5 Br 0.52415(6) 0.25090(12) 0.75635(3) 0.0406(2) Uani 1 1 d . . . Cd1 Cd 0.53188(4) 0.49640(9) 0.66629(3) 0.0399(2) Uani 1 1 d . . . H14 H 0.385(6) 0.014(11) 0.529(4) 0.08(3) Uiso 1 1 d . . . H6 H 0.201(5) 0.360(9) 0.538(3) 0.04(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.048(6) 0.049(6) 0.040(5) -0.007(5) 0.024(4) -0.002(5) C2 0.061(7) 0.071(8) 0.048(6) -0.010(6) 0.026(5) -0.015(6) C3 0.084(8) 0.074(8) 0.036(5) -0.007(6) 0.017(6) 0.003(7) C4 0.051(6) 0.053(7) 0.053(6) -0.007(5) 0.005(5) -0.001(6) C5 0.053(7) 0.101(9) 0.054(6) 0.013(6) 0.012(5) -0.021(7) C6 0.057(7) 0.089(9) 0.041(6) 0.017(6) 0.014(5) -0.015(7) C7 0.041(5) 0.036(5) 0.049(5) 0.003(5) 0.010(4) -0.007(5) C8 0.050(6) 0.049(7) 0.057(6) -0.018(5) 0.020(5) -0.007(6) C9 0.072(8) 0.050(7) 0.073(7) 0.000(6) 0.027(6) 0.005(6) C10 0.043(6) 0.049(7) 0.066(7) 0.009(6) -0.001(5) -0.001(6) C11 0.074(8) 0.048(7) 0.074(7) -0.016(6) 0.011(6) -0.009(7) C12 0.044(6) 0.048(7) 0.066(7) -0.001(5) 0.015(5) -0.001(5) C13 0.042(5) 0.041(6) 0.041(5) 0.005(5) 0.001(4) 0.003(5) C14 0.032(5) 0.056(7) 0.056(6) 0.002(5) 0.009(5) -0.002(6) C15 0.056(6) 0.065(7) 0.038(5) -0.002(5) 0.013(5) 0.013(6) C16 0.047(6) 0.057(7) 0.046(6) -0.006(5) 0.007(5) -0.007(5) C17 0.043(6) 0.098(10) 0.060(6) 0.001(7) 0.014(5) 0.000(6) C18 0.046(6) 0.098(9) 0.039(5) 0.011(6) 0.013(5) -0.003(7) N1 0.066(5) 0.068(6) 0.046(4) -0.003(4) 0.030(4) -0.012(5) N2 0.052(5) 0.054(6) 0.064(5) 0.000(4) 0.020(4) 0.005(5) N3 0.046(5) 0.049(5) 0.044(4) 0.004(4) 0.001(4) 0.000(4) Cl1 0.0652(19) 0.127(3) 0.083(2) -0.010(2) -0.0068(16) -0.013(2) Cl2 0.0523(17) 0.101(3) 0.129(3) 0.001(2) 0.0143(17) -0.0187(19) Cl3 0.0571(17) 0.103(2) 0.0611(16) -0.0170(17) -0.0103(13) -0.0079(17) Br1 0.0628(6) 0.0459(6) 0.0455(5) -0.0070(5) 0.0254(5) -0.0084(6) Br2 0.0399(5) 0.0492(7) 0.0424(5) 0.0027(5) 0.0086(4) 0.0009(5) Br3 0.0655(6) 0.0469(6) 0.0413(5) 0.0088(5) 0.0173(5) 0.0103(6) Br4 0.0434(6) 0.0692(8) 0.0438(5) -0.0037(5) 0.0036(4) -0.0008(6) Br5 0.0469(6) 0.0385(5) 0.0386(5) 0.0036(4) 0.0136(4) -0.0018(5) Cd1 0.0427(4) 0.0417(4) 0.0361(3) -0.0002(3) 0.0087(3) -0.0027(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 C1 C6 1.352(11) . ? C1 C2 1.363(12) . ? C1 N1 1.485(10) . ? C2 C3 1.377(12) . ? C2 H2D 0.9300 . ? C3 C4 1.379(12) . ? C3 H3D 0.9300 . ? C4 C5 1.341(12) . ? C4 Cl1 1.747(9) . ? C5 C6 1.393(12) . ? C5 H5A 0.9300 . ? C6 H6 0.92(7) . ? C7 C8 1.344(11) . ? C7 C12 1.376(12) . ? C7 N2 1.455(10) . ? C8 C9 1.392(12) . ? C8 H8A 0.9300 . ? C9 C10 1.365(13) . ? C9 H9A 0.9300 . ? C10 C11 1.345(12) . ? C10 Cl2 1.749(10) . ? C11 C12 1.381(12) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C18 1.367(11) . ? C13 C14 1.376(11) . ? C13 N3 1.480(9) . ? C14 C15 1.358(11) . ? C14 H14 0.96(9) . ? C15 C16 1.367(11) . ? C15 H15A 0.9300 . ? C16 C17 1.364(11) . ? C16 Cl3 1.753(9) . ? C17 C18 1.364(12) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? Br1 Cd1 2.7444(11) . ? Br2 Cd1 2.6934(11) . ? Br3 Cd1 2.7285(11) . ? Br4 Cd1 2.7457(12) . ? Br5 Cd1 2.8808(11) . ? Br5 Cd1 2.9281(11) 2_646 ? Cd1 Br5 2.9281(11) 2_656 ? 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 C6 C1 C2 121.9(9) . . ? C6 C1 N1 119.4(8) . . ? C2 C1 N1 118.6(8) . . ? C1 C2 C3 119.6(9) . . ? C1 C2 H2D 120.2 . . ? C3 C2 H2D 120.2 . . ? C2 C3 C4 118.0(9) . . ? C2 C3 H3D 121.0 . . ? C4 C3 H3D 121.0 . . ? C5 C4 C3 122.3(9) . . ? C5 C4 Cl1 119.7(8) . . ? C3 C4 Cl1 118.0(8) . . ? C4 C5 C6 119.2(9) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C1 C6 C5 118.8(9) . . ? C1 C6 H6 128(5) . . ? C5 C6 H6 112(5) . . ? C8 C7 C12 121.6(9) . . ? C8 C7 N2 120.7(9) . . ? C12 C7 N2 117.6(8) . . ? C7 C8 C9 119.2(9) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C10 C9 C8 119.0(10) . . ? C10 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C11 C10 C9 121.5(10) . . ? C11 C10 Cl2 120.1(9) . . ? C9 C10 Cl2 118.4(9) . . ? C10 C11 C12 119.8(10) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C7 C12 C11 118.7(9) . . ? C7 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C18 C13 C14 121.8(8) . . ? C18 C13 N3 118.8(8) . . ? C14 C13 N3 119.4(8) . . ? C15 C14 C13 118.7(9) . . ? C15 C14 H14 126(5) . . ? C13 C14 H14 115(5) . . ? C14 C15 C16 119.6(9) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C17 C16 C15 121.7(9) . . ? C17 C16 Cl3 118.5(7) . . ? C15 C16 Cl3 119.8(7) . . ? C18 C17 C16 119.2(9) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C17 C18 C13 119.0(8) . . ? C17 C18 H18A 120.5 . . ? C13 C18 H18A 120.5 . . ? 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 . . ? C7 N2 H2A 109.5 . . ? C7 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C7 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C13 N3 H3A 109.5 . . ? C13 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C13 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? Cd1 Br5 Cd1 165.40(3) . 2_646 ? Br2 Cd1 Br3 94.56(4) . . ? Br2 Cd1 Br1 101.47(4) . . ? Br3 Cd1 Br1 94.93(3) . . ? Br2 Cd1 Br4 161.90(4) . . ? Br3 Cd1 Br4 95.73(4) . . ? Br1 Cd1 Br4 92.44(3) . . ? Br2 Cd1 Br5 83.64(3) . . ? Br3 Cd1 Br5 177.11(4) . . ? Br1 Cd1 Br5 87.65(4) . . ? Br4 Cd1 Br5 85.44(3) . . ? Br2 Cd1 Br5 84.07(3) . 2_656 ? Br3 Cd1 Br5 88.43(4) . 2_656 ? Br1 Cd1 Br5 173.24(4) . 2_656 ? Br4 Cd1 Br5 81.37(3) . 2_656 ? Br5 Cd1 Br5 89.13(2) . 2_656 ? 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 C6 C1 C2 C3 1.3(16) . . . . ? N1 C1 C2 C3 179.5(9) . . . . ? C1 C2 C3 C4 -0.3(16) . . . . ? C2 C3 C4 C5 -1.7(17) . . . . ? C2 C3 C4 Cl1 178.1(8) . . . . ? C3 C4 C5 C6 2.8(17) . . . . ? Cl1 C4 C5 C6 -177.0(9) . . . . ? C2 C1 C6 C5 -0.2(17) . . . . ? N1 C1 C6 C5 -178.4(9) . . . . ? C4 C5 C6 C1 -1.8(17) . . . . ? C12 C7 C8 C9 -2.6(15) . . . . ? N2 C7 C8 C9 179.2(8) . . . . ? C7 C8 C9 C10 2.0(15) . . . . ? C8 C9 C10 C11 -0.8(16) . . . . ? C8 C9 C10 Cl2 179.1(7) . . . . ? C9 C10 C11 C12 0.2(16) . . . . ? Cl2 C10 C11 C12 -179.7(7) . . . . ? C8 C7 C12 C11 2.0(14) . . . . ? N2 C7 C12 C11 -179.7(8) . . . . ? C10 C11 C12 C7 -0.8(15) . . . . ? C18 C13 C14 C15 -0.8(16) . . . . ? N3 C13 C14 C15 178.8(8) . . . . ? C13 C14 C15 C16 0.4(15) . . . . ? C14 C15 C16 C17 1.7(16) . . . . ? C14 C15 C16 Cl3 -179.8(8) . . . . ? C15 C16 C17 C18 -3.3(17) . . . . ? Cl3 C16 C17 C18 178.1(8) . . . . ? C16 C17 C18 C13 2.9(17) . . . . ? C14 C13 C18 C17 -0.9(17) . . . . ? N3 C13 C18 C17 179.6(9) . . . . ? Cd1 Br5 Cd1 Br2 170.99(15) 2_646 . . . ? Cd1 Br5 Cd1 Br3 119.4(7) 2_646 . . . ? Cd1 Br5 Cd1 Br1 -87.19(16) 2_646 . . . ? Cd1 Br5 Cd1 Br4 5.45(16) 2_646 . . . ? Cd1 Br5 Cd1 Br5 86.86(16) 2_646 . . 2_656 ? 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 Br4 0.89 2.43 3.316(6) 173.6 . N3 H3A Br4 0.89 2.67 3.411(7) 141.8 . N3 H3A Br5 0.89 3.00 3.514(6) 118.3 . N3 H3B Br1 0.89 2.61 3.398(7) 148.9 . N1 H1B Br1 0.89 2.65 3.421(7) 146.0 3_666 N1 H1C Br3 0.89 2.47 3.309(7) 158.0 3_666 N2 H2A Br2 0.89 2.53 3.327(7) 149.4 3_666 N2 H2C Br3 0.89 2.83 3.562(7) 140.9 3_666 N2 H2A Br5 0.89 3.00 3.497(7) 117.1 4_565 N2 H2B Br4 0.89 3.12 3.588(7) 115.2 4_565 N2 H2B Br5 0.89 2.59 3.428(7) 158.2 3_656 N2 H2C Br1 0.89 2.92 3.555(7) 129.9 3_656 N3 H3A Br2 0.89 3.14 3.554(7) 110.9 2_646 N3 H3C Br5 0.89 2.54 3.388(6) 160.7 2_646 N3 H3B Br3 0.89 3.09 3.638(7) 121.6 1_545 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.669 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.144 data_zhaodan1109062 _database_code_depnum_ccdc_archive 'CCDC 844699' #TrackingRef 'zhaodan1109062.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H7 Br Cl N' _chemical_formula_sum 'C6 H7 Br Cl N' _chemical_formula_weight 208.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.4980(6) _cell_length_b 6.1858(8) _cell_length_c 14.4538(18) _cell_angle_alpha 90.9386(17) _cell_angle_beta 94.9448(17) _cell_angle_gamma 100.0386(13) _cell_volume 394.33(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1739 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 26.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 5.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2075 _exptl_absorpt_correction_T_max 0.8533 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _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 'Bruker APEX2 CCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 4439 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 27.54 _reflns_number_total 1774 _reflns_number_gt 1113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite (Bruker,2005)' _computing_data_reduction 'APEX2 Software Suite (Bruker,2005)' _computing_structure_solution 'SIR97 (Altomare,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'WINGX (Farrugia,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^)+(0.0248P)^2^+2.4833P] 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 1774 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1803 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.59094(19) 0.74119(13) 0.92282(10) 0.1016(6) Uani 1 1 d . . . C1 C 0.003(2) 0.2663(17) 0.8041(11) 0.096(4) Uani 1 1 d . . . C2 C 0.140(2) 0.0955(19) 0.7824(12) 0.106(4) Uani 1 1 d . . . H2 H 0.1630 -0.0124 0.8252 0.127 Uiso 1 1 calc R . . C3 C 0.243(3) 0.085(3) 0.6966(18) 0.146(7) Uani 1 1 d . . . H3 H 0.3435 -0.0270 0.6806 0.176 Uiso 1 1 calc R . . C4 C 0.196(3) 0.240(5) 0.6359(15) 0.159(8) Uani 1 1 d . . . C5 C 0.059(4) 0.413(3) 0.6583(16) 0.146(6) Uani 1 1 d . . . H5 H 0.0335 0.5188 0.6149 0.175 Uiso 1 1 calc R . . C6 C -0.039(3) 0.429(2) 0.7452(13) 0.117(5) Uani 1 1 d . . . H6 H -0.1304 0.5455 0.7627 0.141 Uiso 1 1 calc R . . Cl1 Cl 0.3177(11) 0.2273(13) 0.5220(5) 0.234(3) Uani 1 1 d . . . N1 N -0.1052(17) 0.2753(11) 0.8971(8) 0.100(3) Uani 1 1 d . . . H1A H -0.2228 0.1482 0.9074 0.149 Uiso 1 1 calc R . . H1B H -0.2110 0.3836 0.9004 0.149 Uiso 1 1 calc R . . H1C H 0.0528 0.2994 0.9398 0.149 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 0.0484(5) 0.0442(5) 0.2098(14) -0.0107(6) -0.0195(6) 0.0185(3) C1 0.041(5) 0.067(6) 0.173(12) -0.026(7) -0.011(6) 0.005(4) C2 0.049(5) 0.083(7) 0.184(14) -0.019(8) -0.005(7) 0.013(5) C3 0.058(7) 0.146(15) 0.23(2) -0.057(15) -0.003(11) 0.011(8) C4 0.055(8) 0.22(2) 0.18(2) -0.048(17) -0.013(10) -0.015(11) C5 0.087(10) 0.158(16) 0.169(18) 0.010(13) -0.038(11) -0.018(10) C6 0.081(8) 0.091(9) 0.170(15) -0.010(10) -0.027(9) 0.006(6) Cl1 0.104(3) 0.345(9) 0.224(6) -0.072(6) 0.018(4) -0.031(4) N1 0.052(4) 0.047(4) 0.196(11) -0.011(5) -0.022(5) 0.016(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 C1 C2 1.356(14) . ? C1 C6 1.358(17) . ? C1 N1 1.473(15) . ? C2 C3 1.36(2) . ? C2 H2 0.9300 . ? C3 C4 1.34(3) . ? C3 H3 0.9300 . ? C4 C5 1.37(3) . ? C4 Cl1 1.78(2) . ? C5 C6 1.37(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? 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 C2 C1 C6 124.0(15) . . ? C2 C1 N1 117.9(13) . . ? C6 C1 N1 118.1(11) . . ? C1 C2 C3 118.6(15) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.9(19) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 122(2) . . ? C3 C4 Cl1 120(2) . . ? C5 C4 Cl1 118(2) . . ? C4 C5 C6 120(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 116.5(16) . . ? C1 C6 H6 121.8 . . ? C5 C6 H6 121.8 . . ? 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 . . ? 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 C6 C1 C2 C3 0.3(17) . . . . ? N1 C1 C2 C3 -179.8(10) . . . . ? C1 C2 C3 C4 -2(2) . . . . ? C2 C3 C4 C5 3(2) . . . . ? C2 C3 C4 Cl1 -178.3(9) . . . . ? C3 C4 C5 C6 -1(2) . . . . ? Cl1 C4 C5 C6 179.8(10) . . . . ? C2 C1 C6 C5 1.3(17) . . . . ? N1 C1 C6 C5 -178.7(10) . . . . ? C4 C5 C6 C1 -1(2) . . . . ? 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 Br1 0.89 2.53 3.387(7) 161.7 1_445 N1 H1B Br1 0.89 2.55 3.426(7) 168.1 1_455 N1 H1C Br1 0.89 2.49 3.345(9) 162.1 2_667 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.592 _refine_diff_density_min -1.225 _refine_diff_density_rms 0.112