############################################################################## # # # 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_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2012-06-09 _journal_date_accepted 2012-06-25 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2012 _journal_volume 68 _journal_issue 7 _journal_page_first o2242 _journal_page_last o2243 _journal_paper_category QO _journal_paper_doi 10.1107/S160053681202870X _journal_coeditor_code SU2459 _publ_contact_author_name 'Prof. Tahir, Muhammad Nawaz ' _publ_contact_author_address ; Department of Physics University of Sargodha Punjab, Pakistan ; _publ_contact_author_email 'dmntahir_uos@yahoo.com, zsrkk@yahoo.com' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ;\ 4,6-Dichloro-2-[(E)-(2-{[(E)-3,5-dichloro-2-oxidobenzylidene]\ azaniumyl}ethyl)iminiumylmethyl]phenolate ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Kia, Reza' ; Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\"ottingen, Germany. ; ; Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran ; 'Kargar, Hadi' . ; Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of Iran ; 'Adabi Ardakani, Amir' . ; Ardakan Branch, Islamic Azad University, Ardakan, Iran ; 'Tahir, Muhammad Nawaz' . ; Department of Physics University of Sargodha Punjab, Pakistan ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-Dichloro-2-[(E)-(2-{[(E)-3,5-dichloro-2- oxidobenzylidene]azaniumyl}ethyl)iminiumylmethyl]phenolate ; _chemical_name_common ; ; _chemical_formula_moiety 'C16 H12 Cl4 N2 O2' _chemical_formula_sum 'C16 H12 Cl4 N2 O2' _chemical_formula_iupac 'C16 H12 Cl4 N2 O2' _chemical_formula_weight 406.08 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.0505(14) _cell_length_b 10.1460(9) _cell_length_c 9.0579(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.955(4) _cell_angle_gamma 90.00 _cell_volume 1670.6(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 936 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 291(2) _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_absorpt_correction_T_min 0.8635 _exptl_absorpt_correction_T_max 0.9315 _exptl_special_details ? _diffrn_ambient_temperature 291(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 ; Bruker SMART APEXII CCD area-detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6453 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _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^ > 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. ; _reflns_number_total 1838 _reflns_number_gt 1146 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.0969 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_number_reflns 1838 _refine_ls_number_parameters 109 _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^)+(0.0431P)^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 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.279 _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' 'O' 'O' 0.0106 0.0060 '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' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' 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 C C1 0.15792(12) 0.3326(2) 0.9612(3) 0.0382(6) Uani d . 1 1 . . C C2 0.13797(12) 0.1976(3) 0.9247(3) 0.0402(6) Uani d . 1 1 . . C C3 0.09283(12) 0.1562(3) 0.7713(3) 0.0451(6) Uani d . 1 1 . . H H3 0.0814 0.0672 0.7511 0.054 Uiso calc R 1 1 . . C C4 0.06374(12) 0.2481(3) 0.6446(3) 0.0456(7) Uani d . 1 1 . . C C5 0.07928(12) 0.3784(3) 0.6728(3) 0.0444(6) Uani d . 1 1 . . H H5 0.0591 0.4384 0.5877 0.053 Uiso calc R 1 1 . . C C6 0.12553(12) 0.4231(2) 0.8292(3) 0.0376(6) Uani d . 1 1 . . C C7 0.14430(12) 0.5599(3) 0.8529(3) 0.0413(6) Uani d . 1 1 . . H H7 0.1217 0.6175 0.7661 0.050 Uiso calc R 1 1 . . Cl Cl1 0.17398(4) 0.08447(7) 1.08141(8) 0.0568(2) Uani d . 1 1 . . Cl Cl2 0.00981(4) 0.19341(9) 0.44794(8) 0.0718(3) Uani d . 1 1 . . N N1 0.19105(10) 0.6061(2) 0.9888(2) 0.0432(5) Uani d . 1 1 . . H H1 0.2100 0.5376 1.0712 0.052 Uiso d R 1 1 . . C C8 0.21355(13) 0.7436(3) 1.0075(3) 0.0479(6) Uani d . 1 1 . . H H8A 0.2193 0.7756 1.1130 0.057 Uiso calc R 1 1 . . H H8B 0.1761 0.7963 0.9242 0.057 Uiso calc R 1 1 . . O O1 0.20257(9) 0.37045(17) 1.10541(17) 0.0482(5) Uani d . 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 C1 0.0382(12) 0.0382(16) 0.0418(14) -0.0014(11) 0.0203(11) -0.0028(12) C2 0.0407(12) 0.0379(16) 0.0450(13) 0.0008(11) 0.0210(11) 0.0003(12) C3 0.0474(14) 0.0370(16) 0.0545(16) -0.0089(12) 0.0250(13) -0.0078(13) C4 0.0430(14) 0.0510(19) 0.0432(15) -0.0101(12) 0.0185(12) -0.0109(13) C5 0.0411(13) 0.0533(19) 0.0395(13) -0.0013(12) 0.0176(11) 0.0036(13) C6 0.0385(12) 0.0374(16) 0.0408(13) -0.0017(11) 0.0206(11) 0.0008(12) C7 0.0443(14) 0.0415(17) 0.0424(13) 0.0029(11) 0.0224(12) 0.0030(12) Cl1 0.0654(4) 0.0412(4) 0.0622(4) 0.0037(3) 0.0253(4) 0.0099(3) Cl2 0.0669(5) 0.0858(7) 0.0498(4) -0.0168(4) 0.0119(4) -0.0205(4) N1 0.0539(12) 0.0323(14) 0.0452(12) -0.0036(10) 0.0227(10) 0.0003(10) C8 0.0610(15) 0.0300(16) 0.0576(16) -0.0066(12) 0.0298(14) -0.0038(12) O1 0.0571(10) 0.0443(12) 0.0361(9) -0.0042(9) 0.0128(8) 0.0005(8) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 . 1.292(2) ? C1 C2 . 1.426(3) ? C1 C6 . 1.429(3) ? C2 C3 . 1.366(3) ? C2 Cl1 . 1.729(2) ? C3 C4 . 1.401(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.358(4) ? C4 Cl2 . 1.740(2) ? C5 C6 . 1.401(3) ? C5 H5 . 0.9300 ? C6 C7 . 1.430(3) ? C7 N1 . 1.281(3) ? C7 H7 . 0.9300 ? N1 C8 . 1.453(3) ? N1 H1 . 0.9724 ? C8 C8 7_567 1.529(5) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? 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 O1 C1 C2 . . 121.8(2) ? O1 C1 C6 . . 122.1(2) ? C2 C1 C6 . . 116.1(2) ? C3 C2 C1 . . 122.2(2) ? C3 C2 Cl1 . . 119.9(2) ? C1 C2 Cl1 . . 117.91(18) ? C2 C3 C4 . . 119.8(2) ? C2 C3 H3 . . 120.1 ? C4 C3 H3 . . 120.1 ? C5 C4 C3 . . 120.8(2) ? C5 C4 Cl2 . . 119.8(2) ? C3 C4 Cl2 . . 119.4(2) ? C4 C5 C6 . . 120.5(2) ? C4 C5 H5 . . 119.8 ? C6 C5 H5 . . 119.8 ? C5 C6 C1 . . 120.7(2) ? C5 C6 C7 . . 119.1(2) ? C1 C6 C7 . . 120.0(2) ? N1 C7 C6 . . 122.7(2) ? N1 C7 H7 . . 118.7 ? C6 C7 H7 . . 118.7 ? C7 N1 C8 . . 121.9(2) ? C7 N1 H1 . . 111.5 ? C8 N1 H1 . . 126.5 ? N1 C8 C8 . 7_567 109.5(3) ? N1 C8 H8A . . 109.8 ? C8 C8 H8A 7_567 . 109.8 ? N1 C8 H8B . . 109.8 ? C8 C8 H8B 7_567 . 109.8 ? H8A C8 H8B . . 108.2 ? 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 O1 C1 C2 C3 . . . . -177.7(2) ? C6 C1 C2 C3 . . . . 2.4(3) ? O1 C1 C2 Cl1 . . . . 1.4(3) ? C6 C1 C2 Cl1 . . . . -178.53(15) ? C1 C2 C3 C4 . . . . -1.0(3) ? Cl1 C2 C3 C4 . . . . 180.00(17) ? C2 C3 C4 C5 . . . . -0.7(3) ? C2 C3 C4 Cl2 . . . . 177.00(17) ? C3 C4 C5 C6 . . . . 0.8(3) ? Cl2 C4 C5 C6 . . . . -176.92(17) ? C4 C5 C6 C1 . . . . 0.8(3) ? C4 C5 C6 C7 . . . . 176.3(2) ? O1 C1 C6 C5 . . . . 177.77(19) ? C2 C1 C6 C5 . . . . -2.3(3) ? O1 C1 C6 C7 . . . . 2.3(3) ? C2 C1 C6 C7 . . . . -177.81(19) ? C5 C6 C7 N1 . . . . -173.9(2) ? C1 C6 C7 N1 . . . . 1.6(3) ? C6 C7 N1 C8 . . . . 175.4(2) ? C7 N1 C8 C8 . . . 7_567 -97.9(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O1 . 0.97 1.74 2.585(3) 143 y C8 H8A O1 4_557 0.97 2.55 3.436(3) 152 y