############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dibromido(2,9-dimethyl-1,10-phenanthroline-\k^2^N,N')zinc ; _chemical_name_common ? _chemical_formula_moiety 'C14 H12 Br2 N2 Zn' _chemical_formula_sum 'C14 H12 Br2 N2 Zn' _chemical_formula_iupac '[Zn Br2 (C14 H12 N2)]' _chemical_formula_weight 433.45 _chemical_melting_point ? _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 9.4113(19) _cell_length_b 18.424(4) _cell_length_c 9.3362(19) _cell_angle_alpha 90.00 _cell_angle_beta 112.59(3) _cell_angle_gamma 90.00 _cell_volume 1494.6(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4014 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 29.23 _cell_measurement_temperature 298(2) _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 6.976 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; [shape of crystal determined optically (X-RED32; Stoe & Cie, (2005)] ; _exptl_absorpt_correction_T_min 0.2744 _exptl_absorpt_correction_T_max 0.3834 _exptl_special_details ; ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_reflns_number 11850 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_full 29.23 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(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. ; _reflns_number_total 4014 _reflns_number_gt 2304 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_gt 0.0858 _refine_ls_wR_factor_ref 0.0999 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_number_reflns 4014 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.404 _refine_diff_density_min -0.666 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' 'Zn' 'Zn' 0.2839 1.4301 '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' _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2005)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn1 0.66996(6) 0.13233(3) 0.75289(6) 0.03618(15) Uani d . 1 1 . . Br Br1 0.79790(8) 0.24221(4) 0.77098(8) 0.0667(2) Uani d . 1 1 . . Br Br2 0.74325(7) 0.03299(3) 0.63755(6) 0.05122(17) Uani d . 1 1 . . N N1 0.6409(4) 0.1030(2) 0.9541(4) 0.0317(8) Uani d . 1 1 . . N N2 0.4348(4) 0.1459(2) 0.6749(4) 0.0349(9) Uani d . 1 1 . . C C1 0.9118(6) 0.0852(3) 1.1082(6) 0.0514(14) Uani d . 1 1 . . H H1A 0.9226 0.0590 1.0240 0.077 Uiso calc R 1 1 . . H H1B 0.9740 0.0627 1.2047 0.077 Uiso calc R 1 1 . . H H1C 0.9447 0.1345 1.1074 0.077 Uiso calc R 1 1 . . C C2 0.7466(5) 0.0842(3) 1.0900(5) 0.0359(10) Uani d . 1 1 . . C C3 0.7030(6) 0.0634(3) 1.2131(5) 0.0429(12) Uani d . 1 1 . . H H3 0.7775 0.0492 1.3077 0.051 Uiso calc R 1 1 . . C C4 0.5507(6) 0.0641(3) 1.1932(6) 0.0434(12) Uani d . 1 1 . . H H4 0.5217 0.0492 1.2733 0.052 Uiso calc R 1 1 . . C C5 0.4398(6) 0.0872(3) 1.0528(5) 0.0376(11) Uani d . 1 1 . . C C6 0.4904(5) 0.1057(2) 0.9352(5) 0.0318(10) Uani d . 1 1 . . C C7 0.2784(7) 0.0920(3) 1.0226(7) 0.0479(13) Uani d . 1 1 . . H H7 0.2437 0.0787 1.0996 0.058 Uiso calc R 1 1 . . C C8 0.1774(6) 0.1151(3) 0.8858(7) 0.0561(15) Uani d . 1 1 . . H H8 0.0740 0.1188 0.8706 0.067 Uiso calc R 1 1 . . C C9 0.2244(6) 0.1343(3) 0.7625(6) 0.0442(12) Uani d . 1 1 . . C C10 0.3796(5) 0.1290(3) 0.7864(5) 0.0346(10) Uani d . 1 1 . . C C11 0.1239(6) 0.1607(3) 0.6167(7) 0.0557(14) Uani d . 1 1 . . H H11 0.0195 0.1660 0.5956 0.067 Uiso calc R 1 1 . . C C12 0.1803(6) 0.1781(3) 0.5082(6) 0.0549(14) Uani d . 1 1 . . H H12 0.1140 0.1956 0.4124 0.066 Uiso calc R 1 1 . . C C13 0.3386(6) 0.1702(3) 0.5378(6) 0.0442(12) Uani d . 1 1 . . C C14 0.4045(7) 0.1888(3) 0.4201(6) 0.0588(15) Uani d . 1 1 . . H H14A 0.4686 0.2310 0.4535 0.088 Uiso calc R 1 1 . . H H14B 0.3224 0.1985 0.3222 0.088 Uiso calc R 1 1 . . H H14C 0.4648 0.1488 0.4089 0.088 Uiso calc R 1 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Zn1 0.0290(3) 0.0397(3) 0.0402(3) 0.0015(3) 0.0137(2) 0.0058(2) Br1 0.0542(4) 0.0502(4) 0.0879(5) -0.0154(3) 0.0186(3) 0.0098(3) Br2 0.0539(4) 0.0554(4) 0.0464(3) 0.0142(3) 0.0216(3) 0.0027(3) N1 0.028(2) 0.032(2) 0.035(2) 0.0023(17) 0.0115(17) 0.0016(16) N2 0.032(2) 0.035(2) 0.0329(19) 0.0022(18) 0.0073(16) -0.0006(17) C1 0.037(3) 0.062(4) 0.050(3) 0.005(3) 0.011(3) 0.003(3) C2 0.033(3) 0.034(3) 0.035(2) 0.001(2) 0.007(2) -0.0042(19) C3 0.049(3) 0.041(3) 0.033(2) 0.002(3) 0.008(2) 0.000(2) C4 0.056(3) 0.041(3) 0.039(3) -0.002(3) 0.024(3) 0.000(2) C5 0.039(3) 0.032(3) 0.047(3) -0.005(2) 0.023(2) -0.005(2) C6 0.025(2) 0.027(2) 0.042(2) 0.0005(19) 0.012(2) -0.0028(19) C7 0.046(3) 0.046(3) 0.064(3) 0.000(3) 0.034(3) 0.004(3) C8 0.030(3) 0.061(4) 0.080(4) -0.004(3) 0.024(3) 0.002(3) C9 0.028(2) 0.045(3) 0.056(3) 0.001(2) 0.011(2) -0.002(3) C10 0.024(2) 0.031(3) 0.044(2) 0.000(2) 0.0077(19) -0.001(2) C11 0.025(3) 0.065(4) 0.066(4) 0.011(3) 0.004(2) -0.002(3) C12 0.039(3) 0.058(4) 0.047(3) 0.012(3) -0.006(2) 0.007(3) C13 0.043(3) 0.037(3) 0.044(3) 0.010(2) 0.007(2) -0.001(2) C14 0.066(4) 0.061(4) 0.039(3) 0.013(3) 0.010(3) 0.013(3) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 N2 . 2.062(4) ? Zn1 N1 . 2.071(3) ? Zn1 Br1 . 2.3281(9) ? Zn1 Br2 . 2.3572(8) ? N1 C2 . 1.322(6) ? N1 C6 . 1.360(6) ? N2 C13 . 1.329(6) ? N2 C10 . 1.366(5) ? C1 C2 . 1.498(7) ? C1 H1A . 0.9600 ? C1 H1B . 0.9600 ? C1 H1C . 0.9600 ? C2 C3 . 1.414(6) ? C3 C4 . 1.372(7) ? C3 H3 . 0.9300 ? C4 C5 . 1.392(7) ? C4 H4 . 0.9300 ? C5 C6 . 1.396(6) ? C5 C7 . 1.437(7) ? C6 C10 . 1.445(7) ? C7 C8 . 1.336(8) ? C7 H7 . 0.9300 ? C8 C9 . 1.427(7) ? C8 H8 . 0.9300 ? C9 C10 . 1.394(7) ? C9 C11 . 1.412(8) ? C11 C12 . 1.351(7) ? C11 H11 . 0.9300 ? C12 C13 . 1.414(7) ? C12 H12 . 0.9300 ? C13 C14 . 1.494(7) ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 Zn1 N1 . . 81.63(14) ? N2 Zn1 Br1 . . 112.03(11) ? N1 Zn1 Br1 . . 113.94(11) ? N2 Zn1 Br2 . . 113.29(11) ? N1 Zn1 Br2 . . 112.05(11) ? Br1 Zn1 Br2 . . 118.32(3) ? C2 N1 C6 . . 119.7(4) ? C2 N1 Zn1 . . 128.7(3) ? C6 N1 Zn1 . . 111.5(3) ? C13 N2 C10 . . 119.5(4) ? C13 N2 Zn1 . . 128.5(3) ? C10 N2 Zn1 . . 112.0(3) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? N1 C2 C3 . . 120.3(4) ? N1 C2 C1 . . 118.1(4) ? C3 C2 C1 . . 121.6(4) ? C4 C3 C2 . . 120.1(5) ? C4 C3 H3 . . 120.0 ? C2 C3 H3 . . 120.0 ? C3 C4 C5 . . 119.8(4) ? C3 C4 H4 . . 120.1 ? C5 C4 H4 . . 120.1 ? C4 C5 C6 . . 117.1(4) ? C4 C5 C7 . . 123.9(4) ? C6 C5 C7 . . 119.0(5) ? N1 C6 C5 . . 122.8(4) ? N1 C6 C10 . . 117.8(4) ? C5 C6 C10 . . 119.4(4) ? C8 C7 C5 . . 121.2(4) ? C8 C7 H7 . . 119.4 ? C5 C7 H7 . . 119.4 ? C7 C8 C9 . . 121.5(5) ? C7 C8 H8 . . 119.2 ? C9 C8 H8 . . 119.2 ? C10 C9 C11 . . 116.8(4) ? C10 C9 C8 . . 118.9(5) ? C11 C9 C8 . . 124.2(5) ? N2 C10 C9 . . 123.0(4) ? N2 C10 C6 . . 117.1(4) ? C9 C10 C6 . . 119.9(4) ? C12 C11 C9 . . 119.6(5) ? C12 C11 H11 . . 120.2 ? C9 C11 H11 . . 120.2 ? C11 C12 C13 . . 121.1(5) ? C11 C12 H12 . . 119.5 ? C13 C12 H12 . . 119.5 ? N2 C13 C12 . . 120.0(5) ? N2 C13 C14 . . 117.6(5) ? C12 C13 C14 . . 122.4(5) ? C13 C14 H14A . . 109.5 ? C13 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C13 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 Zn1 N1 C2 . . . . -177.9(4) ? Br1 Zn1 N1 C2 . . . . -67.4(4) ? Br2 Zn1 N1 C2 . . . . 70.3(4) ? N2 Zn1 N1 C6 . . . . 1.1(3) ? Br1 Zn1 N1 C6 . . . . 111.6(3) ? Br2 Zn1 N1 C6 . . . . -110.7(3) ? N1 Zn1 N2 C13 . . . . 176.8(4) ? Br1 Zn1 N2 C13 . . . . 64.3(4) ? Br2 Zn1 N2 C13 . . . . -72.7(4) ? N1 Zn1 N2 C10 . . . . -0.8(3) ? Br1 Zn1 N2 C10 . . . . -113.3(3) ? Br2 Zn1 N2 C10 . . . . 109.7(3) ? C6 N1 C2 C3 . . . . 3.3(7) ? Zn1 N1 C2 C3 . . . . -177.8(3) ? C6 N1 C2 C1 . . . . -177.3(4) ? Zn1 N1 C2 C1 . . . . 1.7(7) ? N1 C2 C3 C4 . . . . -1.5(7) ? C1 C2 C3 C4 . . . . 179.1(5) ? C2 C3 C4 C5 . . . . -1.7(8) ? C3 C4 C5 C6 . . . . 2.8(7) ? C3 C4 C5 C7 . . . . -178.0(5) ? C2 N1 C6 C5 . . . . -2.0(7) ? Zn1 N1 C6 C5 . . . . 178.9(4) ? C2 N1 C6 C10 . . . . 177.8(4) ? Zn1 N1 C6 C10 . . . . -1.3(5) ? C4 C5 C6 N1 . . . . -1.1(7) ? C7 C5 C6 N1 . . . . 179.8(5) ? C4 C5 C6 C10 . . . . 179.1(4) ? C7 C5 C6 C10 . . . . -0.1(7) ? C4 C5 C7 C8 . . . . 179.4(5) ? C6 C5 C7 C8 . . . . -1.5(8) ? C5 C7 C8 C9 . . . . 1.7(9) ? C7 C8 C9 C10 . . . . -0.3(9) ? C7 C8 C9 C11 . . . . -178.5(6) ? C13 N2 C10 C9 . . . . 1.5(7) ? Zn1 N2 C10 C9 . . . . 179.4(4) ? C13 N2 C10 C6 . . . . -177.5(4) ? Zn1 N2 C10 C6 . . . . 0.4(5) ? C11 C9 C10 N2 . . . . -1.9(8) ? C8 C9 C10 N2 . . . . 179.8(5) ? C11 C9 C10 C6 . . . . 177.1(5) ? C8 C9 C10 C6 . . . . -1.3(8) ? N1 C6 C10 N2 . . . . 0.6(6) ? C5 C6 C10 N2 . . . . -179.5(4) ? N1 C6 C10 C9 . . . . -178.4(4) ? C5 C6 C10 C9 . . . . 1.4(7) ? C10 C9 C11 C12 . . . . 1.0(8) ? C8 C9 C11 C12 . . . . 179.2(6) ? C9 C11 C12 C13 . . . . 0.2(9) ? C10 N2 C13 C12 . . . . -0.2(7) ? Zn1 N2 C13 C12 . . . . -177.7(4) ? C10 N2 C13 C14 . . . . 179.4(4) ? Zn1 N2 C13 C14 . . . . 1.9(7) ? C11 C12 C13 N2 . . . . -0.7(9) ? C11 C12 C13 C14 . . . . 179.8(6) ? data_global _journal_date_recd_electronic 2012-05-12 _journal_date_accepted 2012-05-18 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2012 _journal_volume 68 _journal_issue 6 _journal_page_first m811 _journal_page_last m811 _journal_paper_category QM _journal_paper_doi 10.1107/S1600536812022738 _journal_coeditor_code BT5921 _publ_contact_author_name 'Mostafa M. Amini' _publ_contact_author_address ; Department of Chemistry Shahid Beheshti University G.C. Evin Tehran 1983963113 Iran ; _publ_contact_author_email 'm-pouramini@sbu.ac.ir' _publ_contact_author_fax '+98 21 29903109' _publ_contact_author_phone '+98 21 29903109' _publ_section_title ; Dibromido(2,9-dimethyl-1,10-phenanthroline-\k^2^N,N')zinc ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Dehghani, Ali' . ; Department of Chemistry Shahid Beheshti University G.C. Evin Tehran 1983963113 Iran Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran ; 'M. Amini, Mostafa' . ; Department of Chemistry Shahid Beheshti University G.C. Evin Tehran 1983963113 Iran ; 'Najafi, Ezzatollah' . ; Department of Chemistry Shahid Beheshti University G.C. Evin Tehran 1983963113 Iran ; 'Tadjarodi, Azadeh' . ; Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran ; 'Notash, Behrouz' . ; Department of Chemistry Shahid Beheshti University G.C. Evin Tehran 1983963113 Iran ;