# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- all.cif' _audit_creation_method XD2006 # 1. Submission Details _publ_contact_author_name 'Ulli Englert' _publ_contact_author_address ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; _publ_contact_author_email ullrich.englert@ac.rwth-aachen.de _publ_contact_author_fax 0049-241-8092288 _publ_contact_author_phone 0049-241-8094666 _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; # 2. Processing Summary (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. Titl and Author List _publ_section_title ; The halogen bond made visible: Experimental charge density of a very short intermolecular Cl\^A.\^A.\^A.Cl donor-acceptor contact. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' R.Wang ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; T.Dols ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; C.W.Lehmann ; Max-Plank-Institut fuer Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 Muelheim an der Ruhr Germany ; U.Englert ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; # 4. Text _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Bruker (1999). SAINT+. Version 6.02. Program for Reduction of Data Collected on Bruker CCD Area Detector Diffractometer, Bruker AXS Inc., Madison, Wisconson, USA. Bruker (2001). SMART. Version 5.624. Program for Bruker CCD X-ray Diffractometer Control. Bruker AXS Inc., Madison, Wisconson, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A. L. (2003). J. Appl. Cryst. 36, 7. ; _publ_section_figure_captions ; ? ; _publ_section_table_legends ; ? ; _publ_section_acknowledgements ; ? ; data_1iam _database_code_depnum_ccdc_archive 'CCDC 876636' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 Cl8 N2 Zn' _chemical_formula_sum 'C10 H4 Cl8 N2 Zn' _chemical_formula_weight 501.12 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 42 n m' _symmetry_space_group_name_Hall 'P 4n -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, x, z' '-y, -x, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' _cell_length_a 12.4404(3) _cell_length_b 12.4404(3) _cell_length_c 5.2602(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 814.09(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 110066 _cell_measurement_theta_min 1.6275 _cell_measurement_theta_max 54.9981 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 2.811 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.448 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75' ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 81346 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 55.21 _reflns_number_total 5405 _reflns_number_gt 5096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0250P)^2^+0.4557P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.130(6) _refine_ls_number_reflns 5405 _refine_ls_number_parameters 60 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Zn1 Zn 0.5000 0.5000 0.59447(4) 0.00915(2) Uani 1 4 d S . . Cl1 Cl 0.613222(18) 0.613222(18) 0.77430(6) 0.01526(4) Uani 1 2 d S . . Cl2 Cl 0.14160(2) 0.55029(2) -0.04240(6) 0.02032(4) Uani 1 1 d . . . Cl3 Cl 0.238302(16) 0.761698(16) -0.28623(6) 0.01462(4) Uani 1 2 d S . . N1 N 0.40667(5) 0.59333(5) 0.35353(18) 0.01045(10) Uani 1 2 d S . . C3 C 0.29921(6) 0.70079(6) -0.0348(2) 0.01142(12) Uani 1 2 d S . . C2 C 0.25799(6) 0.60619(6) 0.07002(15) 0.01198(9) Uani 1 1 d . . . C1 C 0.31385(6) 0.55470(6) 0.26298(16) 0.01192(9) Uani 1 1 d . . . H1 H 0.289(2) 0.4923(16) 0.342(4) 0.019(5) 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 Zn1 0.00992(3) 0.00992(3) 0.00761(4) 0.000 0.000 0.00216(4) Cl1 0.01648(6) 0.01648(6) 0.01281(8) -0.00379(6) -0.00379(6) -0.00049(8) Cl2 0.01509(7) 0.02128(9) 0.02458(10) 0.00290(8) -0.00895(7) -0.00385(6) Cl3 0.01629(6) 0.01629(6) 0.01128(8) 0.00214(5) -0.00214(5) 0.00621(8) N1 0.01022(15) 0.01022(15) 0.0109(3) 0.00124(14) -0.00124(14) 0.0014(2) C3 0.01212(18) 0.01212(18) 0.0100(3) 0.00120(17) -0.00120(17) 0.0032(2) C2 0.0111(2) 0.0120(2) 0.0128(3) 0.00069(18) -0.00294(17) 0.00039(16) C1 0.0119(2) 0.0110(2) 0.0129(2) 0.00155(18) -0.00210(18) 0.00035(16) _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 Zn1 N1 2.0742(9) . ? Zn1 N1 2.0742(9) 2_665 ? Zn1 Cl1 2.2052(3) . ? Zn1 Cl1 2.2052(3) 2_665 ? Cl2 C2 1.7117(8) . ? Cl3 C3 1.7023(11) . ? N1 C1 1.3384(9) . ? N1 C1 1.3384(9) 4_665 ? C3 C2 1.3970(9) 4_665 ? C3 C2 1.3971(9) . ? C2 C1 1.3869(11) . ? C1 H1 0.93(2) . ? 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 N1 Zn1 N1 104.67(5) . 2_665 ? N1 Zn1 Cl1 105.196(11) . . ? N1 Zn1 Cl1 105.195(11) 2_665 . ? N1 Zn1 Cl1 105.195(11) . 2_665 ? N1 Zn1 Cl1 105.195(11) 2_665 2_665 ? Cl1 Zn1 Cl1 129.20(2) . 2_665 ? C1 N1 C1 119.53(9) . 4_665 ? C1 N1 Zn1 119.96(4) . . ? C1 N1 Zn1 119.96(4) 4_665 . ? C2 C3 C2 117.56(9) 4_665 . ? C2 C3 Cl3 121.21(5) 4_665 . ? C2 C3 Cl3 121.21(5) . . ? C1 C2 C3 119.60(7) . . ? C1 C2 Cl2 119.27(6) . . ? C3 C2 Cl2 121.09(6) . . ? N1 C1 C2 121.80(7) . . ? N1 C1 H1 115.5(15) . . ? C2 C1 H1 122.6(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 55.21 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.063 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.100 data_2iam _database_code_depnum_ccdc_archive 'CCDC 876637' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Cl4 N2 Zn' _chemical_formula_sum 'C10 H8 Cl4 N2 Zn' _chemical_formula_weight 363.35 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' Cl Cl 0.1484 0.1585 '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' _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 7.2699(10) _cell_length_b 7.8257(11) _cell_length_c 13.110(2) _cell_angle_alpha 84.204(6) _cell_angle_beta 89.280(6) _cell_angle_gamma 62.377(5) _cell_volume 656.97(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7277 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 51.58 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.556 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61942 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 54.71 _reflns_number_total 15656 _reflns_number_gt 12077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0200P)^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 15656 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0587 _refine_ls_wR_factor_gt 0.0576 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.003 _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 Zn1 Zn 0.129916(9) 0.235401(9) 0.242973(5) 0.01104(1) Uani 1 1 d . . . Cl1 Cl -0.25456(2) -0.14724(2) 0.470132(11) 0.01513(2) Uani 1 1 d . . . Cl2 Cl -0.42132(2) 0.31521(2) -0.083272(12) 0.01747(3) Uani 1 1 d . . . Cl3 Cl -0.14988(2) 0.481301(19) 0.296881(11) 0.01588(2) Uani 1 1 d . . . Cl4 Cl 0.44429(2) 0.21516(2) 0.241786(12) 0.01840(3) Uani 1 1 d . . . N1 N 0.13996(7) -0.01079(6) 0.31943(4) 0.01147(6) Uani 1 1 d . . . N2 N 0.06223(7) 0.22492(7) 0.09062(4) 0.01219(7) Uani 1 1 d . . . C1 C -0.03317(8) -0.00421(7) 0.36073(4) 0.01192(7) Uani 1 1 d . . . H1 H -0.1594 0.1137 0.3526 0.014 Uiso 1 1 calc R . . C2 C -0.02991(8) -0.16716(7) 0.41506(4) 0.01190(7) Uani 1 1 d . . . C3 C 0.15271(9) -0.34210(8) 0.42617(5) 0.01514(8) Uani 1 1 d . . . H3 H 0.1559 -0.4550 0.4623 0.018 Uiso 1 1 calc R . . C4 C 0.32990(9) -0.34669(8) 0.38295(5) 0.01554(9) Uani 1 1 d . . . H4 H 0.4573 -0.4636 0.3888 0.019 Uiso 1 1 calc R . . C5 C 0.31863(8) -0.17812(8) 0.33100(4) 0.01298(8) Uani 1 1 d . . . H5 H 0.4409 -0.1810 0.3027 0.016 Uiso 1 1 calc R . . C6 C -0.12792(8) 0.25933(8) 0.05875(4) 0.01282(8) Uani 1 1 d . . . H6 H -0.2312 0.2768 0.1076 0.015 Uiso 1 1 calc R . . C7 C -0.17557(8) 0.26964(8) -0.04478(4) 0.01281(8) Uani 1 1 d . . . C8 C -0.02762(9) 0.24529(9) -0.11736(4) 0.01571(9) Uani 1 1 d . . . H8 H -0.0602 0.2561 -0.1884 0.019 Uiso 1 1 calc R . . C9 C 0.16955(10) 0.20464(10) -0.08304(5) 0.01792(10) Uani 1 1 d . . . H9 H 0.2765 0.1828 -0.1302 0.022 Uiso 1 1 calc R . . C10 C 0.20848(9) 0.19625(9) 0.02115(4) 0.01531(9) Uani 1 1 d . . . H10 H 0.3435 0.1692 0.0442 0.018 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 Zn1 0.00959(2) 0.01121(2) 0.01192(2) -0.00014(2) -0.00055(2) -0.00467(2) Cl1 0.01326(5) 0.01639(5) 0.01668(5) -0.00191(4) 0.00314(4) -0.00774(4) Cl2 0.01218(5) 0.02218(6) 0.01844(6) -0.00368(4) -0.00233(4) -0.00797(4) Cl3 0.01371(5) 0.01256(5) 0.01816(5) -0.00230(4) 0.00195(4) -0.00331(4) Cl4 0.01290(5) 0.02480(6) 0.01984(6) 0.00024(5) -0.00200(4) -0.01117(5) N1 0.01032(14) 0.01132(15) 0.01224(15) -0.00067(12) -0.00048(12) -0.00467(12) N2 0.01048(14) 0.01321(16) 0.01225(16) -0.00027(12) -0.00026(12) -0.00518(13) C1 0.01038(16) 0.01138(16) 0.01317(18) -0.00111(13) -0.00016(14) -0.00440(14) C2 0.01142(16) 0.01246(17) 0.01217(17) -0.00147(13) 0.00073(14) -0.00582(14) C3 0.01425(19) 0.01179(18) 0.0174(2) 0.00065(15) 0.00027(16) -0.00483(15) C4 0.01198(18) 0.01204(18) 0.0191(2) 0.00012(16) 0.00019(16) -0.00299(15) C5 0.01049(16) 0.01298(18) 0.01405(18) -0.00152(14) -0.00008(14) -0.00424(14) C6 0.01025(16) 0.01432(18) 0.01344(18) -0.00113(14) 0.00014(14) -0.00541(14) C7 0.01146(17) 0.01302(18) 0.01430(19) -0.00118(14) -0.00122(14) -0.00598(15) C8 0.0167(2) 0.0206(2) 0.01256(19) -0.00185(16) 0.00020(16) -0.01092(18) C9 0.0154(2) 0.0274(3) 0.0140(2) -0.00269(19) 0.00244(17) -0.0125(2) C10 0.01194(18) 0.0207(2) 0.01432(19) -0.00114(16) 0.00084(15) -0.00857(17) _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 Zn1 N1 2.0501(5) . ? Zn1 N2 2.0817(6) . ? Zn1 Cl4 2.2165(3) . ? Zn1 Cl3 2.2246(3) . ? Cl1 C2 1.7234(6) . ? Cl2 C7 1.7231(6) . ? N1 C1 1.3448(7) . ? N1 C5 1.3463(7) . ? N2 C6 1.3434(7) . ? N2 C10 1.3438(8) . ? C1 C2 1.3867(7) . ? C1 H1 0.9500 . ? C2 C3 1.3918(8) . ? C3 C4 1.3873(9) . ? C3 H3 0.9500 . ? C4 C5 1.3895(8) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.3901(8) . ? C6 H6 0.9500 . ? C7 C8 1.3854(8) . ? C8 C9 1.3866(9) . ? C8 H8 0.9500 . ? C9 C10 1.3873(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 N1 Zn1 N2 104.53(2) . . ? N1 Zn1 Cl4 110.275(15) . . ? N2 Zn1 Cl4 104.516(15) . . ? N1 Zn1 Cl3 105.686(17) . . ? N2 Zn1 Cl3 106.014(16) . . ? Cl4 Zn1 Cl3 124.175(11) . . ? C1 N1 C5 119.42(5) . . ? C1 N1 Zn1 119.61(3) . . ? C5 N1 Zn1 120.95(4) . . ? C6 N2 C10 119.10(5) . . ? C6 N2 Zn1 121.72(4) . . ? C10 N2 Zn1 119.02(4) . . ? N1 C1 C2 120.90(5) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 120.37(5) . . ? C1 C2 Cl1 118.70(4) . . ? C3 C2 Cl1 120.92(4) . . ? C4 C3 C2 118.04(5) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 119.15(5) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.10(5) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? N2 C6 C7 120.86(5) . . ? N2 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.53(5) . . ? C8 C7 Cl2 119.73(4) . . ? C6 C7 Cl2 119.74(4) . . ? C7 C8 C9 117.94(5) . . ? C7 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? C8 C9 C10 119.08(5) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? N2 C10 C9 122.45(5) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? 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 N2 Zn1 N1 C1 -91.70(4) . . . . ? Cl4 Zn1 N1 C1 156.48(4) . . . . ? Cl3 Zn1 N1 C1 19.95(4) . . . . ? N2 Zn1 N1 C5 89.85(4) . . . . ? Cl4 Zn1 N1 C5 -21.97(5) . . . . ? Cl3 Zn1 N1 C5 -158.50(4) . . . . ? N1 Zn1 N2 C6 73.10(4) . . . . ? Cl4 Zn1 N2 C6 -171.00(4) . . . . ? Cl3 Zn1 N2 C6 -38.31(4) . . . . ? N1 Zn1 N2 C10 -111.58(4) . . . . ? Cl4 Zn1 N2 C10 4.32(4) . . . . ? Cl3 Zn1 N2 C10 137.01(4) . . . . ? C5 N1 C1 C2 0.08(8) . . . . ? Zn1 N1 C1 C2 -178.39(4) . . . . ? N1 C1 C2 C3 -1.20(8) . . . . ? N1 C1 C2 Cl1 177.66(4) . . . . ? C1 C2 C3 C4 1.04(9) . . . . ? Cl1 C2 C3 C4 -177.79(5) . . . . ? C2 C3 C4 C5 0.18(9) . . . . ? C1 N1 C5 C4 1.19(8) . . . . ? Zn1 N1 C5 C4 179.64(4) . . . . ? C3 C4 C5 N1 -1.32(9) . . . . ? C10 N2 C6 C7 -1.40(8) . . . . ? Zn1 N2 C6 C7 173.91(4) . . . . ? N2 C6 C7 C8 -0.25(8) . . . . ? N2 C6 C7 Cl2 -179.67(4) . . . . ? C6 C7 C8 C9 1.97(9) . . . . ? Cl2 C7 C8 C9 -178.61(5) . . . . ? C7 C8 C9 C10 -2.03(9) . . . . ? C6 N2 C10 C9 1.33(9) . . . . ? Zn1 N2 C10 C9 -174.12(5) . . . . ? C8 C9 C10 N2 0.43(10) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 45.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.203 _refine_diff_density_min -1.090 _refine_diff_density_rms 0.131 data_1multipole _database_code_depnum_ccdc_archive 'CCDC 876638' #TrackingRef '- all.cif' _audit_creation_method XD2006 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 Cl8 N2 Zn' _chemical_formula_sum 'C10 H4 Cl8 N2 Zn' _chemical_formula_weight 501.12 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 42 n m' _symmetry_space_group_name_Hall 'P 4n -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, x, z' '-y, -x, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' _cell_length_a 12.4404(3) _cell_length_b 12.4404(3) _cell_length_c 5.2602(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 814.09(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 110066 _cell_measurement_theta_min 1.6275 _cell_measurement_theta_max 54.9981 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 2.811 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.448 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75' ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 81346 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 55.21 _reflns_number_total 5405 _reflns_number_gt 5050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = q/[s^2^(Fo^2^) + (0.05 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5050 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.031 _refine_ls_R_factor_gt 0.025 _refine_ls_wR_factor_ref 0.075 _refine_ls_goodness_of_fit_ref 1.1399 _refine_ls_shift/su_max 0 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity ZN(1) 0.5 0.5 0.6011 0.01 1 2 CL(1) 0.613253(17) 0.613253(17) 0.78058(10) 0.015 1 4 CL(2) 0.141566(19) 0.55025(2) -0.03591(10) 0.02 1 8 CL(3) 0.238286(15) 0.761714(15) -0.27993(9) 0.015 1 4 N(1) 0.40662(5) 0.59339(5) 0.35972(19) 0.01 1 4 C(3) 0.29921(5) 0.70079(5) -0.0287(2) 0.011 1 4 C(2) 0.25791(5) 0.60621(5) 0.07638(16) 0.012 1 8 C(1) 0.31387(6) 0.55460(5) 0.26936(16) 0.012 1 8 H(1) 0.283569 0.481595 0.355636 0.018 1 8 DUM0 0.5 0.5 0 0 0 1 DUM1 0 0 0.6011 0 0 1 DUM2 1 0.2265 0.7804 0 0 1 DUM3 0 0.5234 -0.2801 0 0 1 DUM4 0 0.1867 0.3596 0 0 1 DUM5 0 0.4015 -0.0287 0 0 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 ZN(1) 0.01044(5) 0.01044(5) 0.00772(7) 0 0 0.00213(6) CL(1) 0.01643(6) 0.01643(6) 0.01281(8) -0.00376(5) -0.00376(5) -0.00053(7) CL(2) 0.01522(7) 0.02138(9) 0.02444(11) 0.00302(8) -0.00901(7) -0.00388(6) CL(3) 0.01627(6) 0.01627(6) 0.01132(8) 0.00214(4) -0.00214(4) 0.00613(7) N(1) 0.01013(14) 0.01013(14) 0.0109(3) 0.00123(15) -0.00123(15) 0.0015(2) C(3) 0.01185(16) 0.01185(16) 0.0103(3) 0.00124(15) -0.00124(15) 0.0030(2) C(2) 0.01112(18) 0.01205(19) 0.0125(2) 0.00098(16) -0.00293(16) 0.00024(14) C(1) 0.01165(19) 0.01095(18) 0.0128(2) 0.00173(16) -0.00226(17) 0.00013(14) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 ZN(1) 2.57(4) 0 0 0 0.054(18) 0.062(10) 0 0 -0.017(9) 0 -0.073(14) 0 0 -0.004(6) 0 0 0 0.013(8) 0 0 0.003(8) 0 0 0 0.014(7) 0 1.126(13) 1.2 1.2 1.2 1.2 1.2 4 9.5908 4 9.5908 4 9.5908 4 9.5908 4 9.5908 CL(1) 3.63(9) 0 -0.09(5) 0.05(4) 0 -0.02(3) 0 0 0.05(3) 0.03(3) 0 -0.05(3) -0.02(2) 0 0 0.00(2) 0.07(3) 0.04(2) 0 0 -0.05(2) 0.03(2) 0 0 0.00(2) -0.03(2) 0.957(7) 1.2 1.2 1.2 1.2 1.2 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 CL(2) 7.73(18) 0 -0.23(7) -0.32(7) -0.08(5) -0.12(4) -0.04(4) 0.09(4) -0.09(5) 0.11(4) -0.10(5) 0.11(4) 0.02(3) 0.10(4) 0.01(5) -0.04(5) -0.19(5) 0.01(4) 0.03(4) -0.11(4) 0.01(4) 0.06(4) -0.01(4) 0.06(4) -0.04(4) 0.04(4) 0.957(7) 1.2 1.2 1.2 1.2 1.2 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 CL(3) 3.91(14) 0 0.05(4) -0.01(5) 0 0.05(3) 0 0 0.06(3) -0.01(3) 0 0.06(3) -0.03(3) 0 0 -0.01(3) 0.02(2) 0.09(2) 0 0 0.05(2) 0.01(2) 0 0 -0.006(19) 0.01(2) 0.957(7) 1.2 1.2 1.2 1.2 1.2 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 N(1) 2.20(16) 0 -0.04(4) 0.09(4) 0 -0.01(3) 0 0 -0.02(3) 0.03(3) 0 -0.03(3) -0.05(3) 0 0 -0.01(3) -0.01(3) -0.05(4) 0 0 -0.07(4) 0.02(3) 0 0 -0.05(3) 0.04(3) 1.01(2) 0.930364 0.930364 0.930364 0.930364 0.930364 2 3.81056 2 3.81056 2 3.81056 3 3.81056 4 3.81056 C(3) 1.9(2) 0 -0.03(9) -0.26(10) 0 0.05(7) 0 0 -0.13(6) -0.01(6) 0 0.08(8) -0.25(9) 0 0 0.15(7) -0.09(6) 0.14(11) 0 0 -0.03(11) -0.12(9) 0 0 0.10(8) 0.13(8) 0.942(17) 0.780646 0.780646 0.780646 0.780646 0.780646 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(2) 3.6(3) 0 0.21(14) 0.05(14) 0.11(14) 0.02(10) -0.10(9) -0.19(9) -0.21(8) 0.14(9) 0.45(13) 0.09(11) -0.08(11) 0.37(12) 0.00(10) -0.03(9) 0.08(10) 0.09(16) 0.04(14) -0.02(16) -0.10(15) 0.18(14) -0.04(13) 0.00(12) 0.21(12) 0.09(12) 0.942(17) 0.780646 0.780646 0.780646 0.780646 0.780646 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(1) 3.9(3) 0 0.08(11) 0.14(14) -0.12(12) 0.07(10) -0.06(8) -0.06(9) -0.31(10) 0.05(9) 0.41(13) -0.08(9) 0.02(11) 0.45(11) -0.18(10) -0.13(11) 0.07(10) -0.38(15) -0.10(12) -0.09(14) -0.18(12) -0.38(13) 0.12(13) 0.14(13) 0.24(13) -0.06(13) 0.942(17) 0.780646 0.780646 0.780646 0.780646 0.780646 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 H(1) 0.95(11) 0 0 0 0.26(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 ZN(1) DUM0 Z ZN(1) DUM1 Y CL(1) DUM2 Z CL(1) ZN(1) Y CL(2) C(2) Z CL(2) C(1) Y CL(3) DUM3 Z CL(3) C(3) Y N(1) DUM4 Z N(1) ZN(1) Y C(3) DUM5 Z C(3) CL(3) Y C(2) C(1) Z C(2) C(3) Y C(1) H(1) Z C(1) N(1) Y H(1) C(1) Z H(1) N(1) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag ZN(1) CL(1) 2.2048(3) 1_555 1_555 yes ZN(1) CL(1) 2.2049(3) 1_555 2_665 yes ZN(1) CL(1) 2.2048(3) 1_555 3_555 yes ZN(1) CL(1) 2.2049(3) 1_555 4_665 yes CL(2) C(2) 1.7113(7) 1_555 1_555 yes CL(3) C(3) 1.7014(9) 1_555 1_555 yes CL(3) C(3) 1.7014(9) 1_555 4_665 yes N(1) C(1) 1.3379(8) 1_555 1_555 yes N(1) C(1) 1.3379(8) 1_555 4_665 yes C(3) C(2) 1.3980(8) 1_555 1_555 yes C(3) C(2) 1.3980(8) 1_555 4_665 yes C(2) C(1) 1.3882(10) 1_555 1_555 yes C(1) H(1) 1.083 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag CL(1) ZN(1) CL(1) 129.30(3) 1_555 1_555 2_665 yes CL(1) ZN(1) CL(1) 129.30(3) 1_555 1_555 4_665 yes CL(1) ZN(1) CL(1) 129.30(3) 2_665 1_555 3_555 yes CL(1) ZN(1) CL(1) 129.30(3) 3_555 1_555 4_665 yes C(1) N(1) C(1) 119.72(8) 1_555 1_555 4_665 yes CL(3) C(3) C(2) 121.23(4) 1_555 1_555 1_555 yes CL(3) C(3) C(2) 121.23(4) 1_555 1_555 4_665 yes CL(3) C(3) C(2) 121.23(4) 4_665 1_555 1_555 yes CL(3) C(3) C(2) 121.23(4) 4_665 1_555 4_665 yes C(2) C(3) C(2) 117.53(8) 1_555 1_555 4_665 yes CL(2) C(2) C(3) 121.11(6) 1_555 1_555 1_555 yes CL(2) C(2) C(3) 121.11(6) 1_555 1_555 4_665 yes CL(2) C(2) C(1) 119.23(5) 1_555 1_555 1_555 yes C(3) C(2) C(1) 119.62(6) 1_555 1_555 1_555 yes C(3) C(2) C(1) 119.62(6) 4_665 1_555 1_555 yes N(1) C(1) C(2) 121.70(6) 1_555 1_555 1_555 yes N(1) C(1) C(2) 121.70(6) 4_665 1_555 1_555 yes N(1) C(1) H(1) 117.0 1_555 1_555 1_555 yes H(1) C(1) C(2) 121.0 1_555 1_555 1_555 yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 55.21 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.925 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.143 data_2multipole _database_code_depnum_ccdc_archive 'CCDC 876639' #TrackingRef '- all.cif' _audit_creation_method XD2006 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Cl4 N2 Zn' _chemical_formula_sum 'C10 H8 Cl4 N2 Zn' _chemical_formula_weight 363.35 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' Cl Cl 0.1484 0.1585 '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' _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 7.2699(10) _cell_length_b 7.8257(11) _cell_length_c 13.110(2) _cell_angle_alpha 84.204(6) _cell_angle_beta 89.280(6) _cell_angle_gamma 62.377(5) _cell_volume 656.97(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7277 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 51.58 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 0.556 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'INCOATEC Microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61942 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 54.71 _reflns_number_total 15656 _reflns_number_gt 12077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'XD2006 (Volkov, 2006)' _computing_publication_material 'XD2006 (Volkov, 2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = q/[s^2^(Fo^2^) + (0.01 P)^2^ + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 15653 _refine_ls_number_parameters 603 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.034 _refine_ls_R_factor_gt 0.022 _refine_ls_wR_factor_ref 0.037 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_shift/su_max 0.00001 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity ZN(1) 0.129906(13) 0.235391(13) 0.242974(7) 0.011 1 2 CL(1) -0.254624(17) -0.147222(16) 0.470115(9) 0.015 1 2 CL(2) -0.421298(18) 0.315172(18) -0.083269(10) 0.017 1 2 CL(3) -0.149872(17) 0.481285(16) 0.296868(9) 0.016 1 2 CL(4) 0.444302(18) 0.215158(19) 0.241793(10) 0.018 1 2 N(1) 0.13994(8) -0.01094(7) 0.31948(4) 0.011 1 2 N(2) 0.06218(8) 0.22485(7) 0.09053(4) 0.012 1 2 C(1) -0.03333(7) -0.00418(7) 0.36080(4) 0.012 1 2 C(2) -0.03011(7) -0.16709(7) 0.41518(4) 0.012 1 2 C(3) 0.15263(9) -0.34221(8) 0.42613(4) 0.015 1 2 C(4) 0.33011(8) -0.34682(8) 0.38278(4) 0.015 1 2 C(5) 0.31891(7) -0.17828(7) 0.33098(4) 0.013 1 2 C(6) -0.12807(7) 0.25934(7) 0.05877(4) 0.013 1 2 C(7) -0.17602(8) 0.26976(7) -0.04486(4) 0.013 1 2 C(8) -0.02769(9) 0.24526(8) -0.11746(4) 0.016 1 2 C(9) 0.16989(9) 0.20452(10) -0.08318(5) 0.018 1 2 C(10) 0.20866(8) 0.19617(8) 0.02114(4) 0.015 1 2 H(1) -0.177206 0.130282 0.351437 0.014 1 2 H(3) 0.156375 -0.470938 0.467372 0.018 1 2 H(4) 0.475317 -0.48011 0.389629 0.019 1 2 H(5) 0.458205 -0.181448 0.298733 0.016 1 2 H(6) -0.245725 0.279319 0.114486 0.015 1 2 H(8) -0.064856 0.257645 -0.198482 0.019 1 2 H(9) 0.291779 0.179728 -0.136976 0.021 1 2 H(10) 0.362595 0.165409 0.047503 0.018 1 2 DUM0 0 0 0 0 0 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 ZN(1) 0.00972(3) 0.01135(3) 0.01121(3) 0.00002(2) -0.00033(2) -0.00493(3) CL(1) 0.01309(4) 0.01602(4) 0.01657(4) -0.00182(3) 0.00303(3) -0.00761(4) CL(2) 0.01202(4) 0.02184(5) 0.01816(5) -0.00369(4) -0.00224(4) -0.00782(4) CL(3) 0.01351(4) 0.01238(4) 0.01802(5) -0.00224(3) 0.00189(3) -0.00327(3) CL(4) 0.01268(4) 0.02453(5) 0.01966(5) 0.00027(4) -0.00195(4) -0.01105(4) N(1) 0.01017(15) 0.01110(16) 0.01256(16) -0.00044(13) -0.00017(13) -0.00466(14) N(2) 0.01036(15) 0.01441(17) 0.01118(16) -0.00060(13) -0.00005(13) -0.00563(14) C(1) 0.01004(15) 0.01075(15) 0.01357(17) -0.00069(13) 0.00027(13) -0.00413(13) C(2) 0.01115(15) 0.01171(16) 0.01246(16) -0.00077(13) 0.00071(13) -0.00535(14) C(3) 0.01382(18) 0.01148(17) 0.0176(2) 0.00129(15) 0.00084(16) -0.00470(15) C(4) 0.01181(17) 0.01162(17) 0.0190(2) 0.00085(15) 0.00046(16) -0.00280(15) C(5) 0.00995(15) 0.01272(17) 0.01456(17) -0.00105(14) 0.00040(13) -0.00425(14) C(6) 0.00991(15) 0.01496(17) 0.01272(17) -0.00125(14) 0.00037(14) -0.00547(14) C(7) 0.01131(16) 0.01399(17) 0.01294(17) -0.00128(14) -0.00085(14) -0.00624(14) C(8) 0.01588(19) 0.0220(2) 0.01194(18) -0.00185(16) 0.00053(16) -0.01128(18) C(9) 0.0153(2) 0.0291(3) 0.01279(19) -0.00292(18) 0.00264(17) -0.0131(2) C(10) 0.01145(17) 0.0220(2) 0.01360(18) -0.00169(16) 0.00090(15) -0.00890(16) #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 ZN(1) 11.134(16) 0 -0.023(9) 0.004(10) -0.028(9) 0.143(12) 0.246(11) -0.250(11) -0.161(12) -0.152(11) -0.046(8) -0.003(8) 0.022(8) -0.025(8) -0.024(8) 0.013(8) 0.014(8) -0.018(12) 0.044(11) -0.039(12) -0.081(12) -0.087(11) 0.086(12) 0.033(12) 0.076(12) -0.271(11) 0.957151 0.75489 0.75489 0.75489 0.75489 0.75489 4 9.5908 4 9.5908 4 9.5908 4 9.5908 4 9.5908 CL(1) 6.90(3) 0 -0.019(16) 0.059(16) -0.042(17) -0.122(17) 0.085(15) 0.195(16) -0.020(15) 0.038(14) 0.123(15) 0.002(14) -0.023(13) 0.001(13) -0.019(13) 0.015(12) -0.017(12) 0.080(16) 0.075(15) -0.013(15) -0.022(15) -0.030(15) -0.057(15) 0.020(14) -0.005(14) 0.101(14) 1.03002 1 1 1 1 1 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 CL(2) 6.66(4) 0 -0.007(16) -0.057(17) -0.032(16) -0.298(16) -0.082(15) -0.026(17) -0.137(16) -0.072(15) 0.076(15) 0.002(14) 0.027(14) 0.016(15) -0.035(13) -0.029(14) 0.013(13) -0.039(17) -0.054(15) -0.091(15) -0.016(16) 0.053(15) -0.053(16) 0.031(15) -0.024(15) 0.123(15) 1.03002 1 1 1 1 1 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 CL(3) 7.69(3) 0 0.024(14) -0.017(14) -0.003(13) -0.122(14) -0.023(15) -0.090(14) -0.036(15) 0.106(14) -0.005(13) 0.021(13) -0.039(12) -0.001(13) -0.018(13) 0.007(13) -0.024(12) 0.116(15) 0.016(14) 0.019(14) -0.064(15) -0.029(15) 0.050(15) 0.062(15) -0.023(14) -0.039(14) 1.025396 1 1 1 1 1 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 CL(4) 7.33(3) 0 -0.021(14) -0.030(15) 0.065(14) -0.103(15) -0.105(14) -0.074(14) -0.081(15) 0.105(14) 0.000(14) -0.010(13) -0.010(14) -0.027(14) -0.028(13) -0.032(14) 0.045(14) -0.051(16) 0.019(14) -0.034(15) -0.061(16) -0.034(15) -0.024(15) -0.092(15) -0.066(15) -0.076(15) 1.025396 1 1 1 1 1 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 4 3.9938571428571 N(1) 5.19(4) 0 0.02(2) -0.15(2) -0.03(2) 0.08(2) -0.036(18) 0.093(19) -0.071(17) 0.017(15) 0.162(19) 0.041(17) 0.033(19) 0.108(17) 0.017(17) 0.002(14) 0.016(15) 0.11(2) -0.035(19) -0.02(2) 0.00(2) -0.02(2) 0.055(18) 0.015(19) -0.036(16) 0.006(16) 0.985237 0.882839 0.882839 0.882839 0.882839 0.882839 2 3.81056 2 3.81056 2 3.81056 3 3.81056 4 3.81056 N(2) 5.14(5) 0 0.00(2) -0.13(2) -0.02(2) -0.03(2) -0.055(18) 0.066(19) -0.219(17) -0.017(17) 0.174(19) -0.012(17) -0.02(2) 0.110(18) -0.014(17) -0.027(15) -0.056(15) 0.01(2) -0.021(19) 0.06(2) -0.02(2) -0.08(2) -0.055(19) 0.02(2) -0.045(17) -0.018(17) 0.985237 0.882839 0.882839 0.882839 0.882839 0.882839 2 3.81056 2 3.81056 2 3.81056 3 3.81056 4 3.81056 C(1) 4.22(6) 0 -0.03(3) 0.04(4) 0.11(3) 0.13(3) 0.03(2) 0.03(3) -0.24(3) -0.05(2) 0.34(3) -0.06(2) 0.09(3) 0.25(3) 0.08(3) -0.04(3) -0.01(3) 0.17(3) 0.04(3) -0.03(4) -0.06(3) 0.05(3) 0.07(3) -0.01(3) -0.01(3) 0.07(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(2) 4.09(7) 0 -0.09(3) 0.19(4) 0.04(4) 0.16(3) -0.10(2) -0.06(3) -0.09(2) 0.00(2) 0.38(3) 0.00(3) 0.02(3) 0.36(3) 0.07(3) 0.01(2) 0.04(2) -0.01(4) -0.03(3) 0.11(4) -0.08(4) -0.12(3) 0.00(3) 0.06(3) -0.02(3) 0.02(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(3) 3.76(8) 0 -0.03(3) 0.04(4) 0.11(4) 0.25(3) -0.13(2) -0.14(3) -0.12(3) 0.08(3) 0.31(3) -0.01(2) 0.00(3) 0.18(3) -0.01(3) -0.02(3) 0.01(3) 0.13(4) -0.06(3) 0.00(4) 0.03(3) -0.02(3) 0.07(3) 0.13(3) 0.02(3) -0.10(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(4) 4.27(8) 0 0.07(3) -0.06(4) 0.08(4) 0.02(3) 0.06(2) 0.04(3) -0.22(3) 0.14(3) 0.37(3) 0.02(2) 0.08(3) 0.21(3) 0.01(3) -0.05(3) -0.02(3) 0.05(4) 0.03(3) 0.03(4) -0.02(3) -0.03(3) 0.11(3) -0.07(3) 0.05(3) 0.02(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(5) 4.29(6) 0 0.04(3) 0.13(4) -0.01(4) 0.29(3) 0.03(2) 0.08(3) -0.13(3) -0.03(2) 0.42(3) -0.04(2) 0.12(3) 0.29(3) -0.06(3) 0.02(3) -0.07(3) -0.06(4) 0.05(3) 0.09(4) -0.10(3) 0.00(3) -0.06(3) 0.09(3) 0.04(3) -0.01(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(6) 4.12(6) 0 0.01(3) 0.18(4) 0.08(4) 0.26(3) 0.05(2) 0.06(3) -0.12(3) 0.00(2) 0.40(3) -0.09(2) 0.06(3) 0.19(3) -0.05(3) -0.01(2) -0.03(3) 0.01(4) 0.04(3) -0.01(4) 0.04(3) -0.02(3) -0.10(3) 0.10(3) -0.03(3) -0.11(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(7) 4.25(7) 0 -0.12(3) 0.21(4) -0.07(4) 0.21(3) 0.06(3) -0.18(3) -0.23(2) -0.02(2) 0.34(4) 0.00(3) 0.02(4) 0.27(3) -0.04(3) 0.01(2) 0.05(2) 0.01(4) -0.05(3) -0.05(4) 0.00(4) -0.10(4) 0.01(3) 0.08(3) 0.13(3) 0.00(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(8) 4.24(8) 0 -0.03(3) -0.06(4) 0.05(4) 0.18(3) -0.07(2) -0.11(3) -0.32(3) 0.08(3) 0.37(4) 0.01(3) 0.01(4) 0.28(3) 0.10(3) 0.02(3) -0.05(3) 0.08(4) -0.01(3) -0.01(4) -0.08(3) 0.01(4) 0.08(3) 0.01(4) 0.00(3) 0.04(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(9) 4.29(8) 0 -0.05(3) -0.01(4) -0.05(4) 0.27(3) -0.06(2) 0.13(3) -0.21(3) -0.05(3) 0.48(4) -0.08(2) 0.05(4) 0.28(3) 0.02(3) 0.07(3) -0.03(3) -0.03(4) -0.09(3) -0.18(4) 0.01(3) -0.04(4) -0.10(3) -0.04(4) 0.04(3) -0.12(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(10) 4.20(7) 0 0.04(3) 0.16(4) 0.11(4) 0.25(3) 0.04(2) 0.02(3) -0.25(3) 0.11(3) 0.33(3) 0.06(2) 0.10(3) 0.28(3) 0.06(3) 0.02(3) 0.05(3) 0.09(4) 0.08(3) 0.23(4) 0.16(3) -0.02(3) 0.06(3) 0.14(3) 0.19(3) 0.00(3) 0.983531 0.838931 0.838931 0.838931 0.838931 0.838931 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 H(1) 0.75(3) 0 0 0 0.088(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(3) 0.84(3) 0 0 0 0.123(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(4) 0.81(3) 0 0 0 0.089(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(5) 0.81(3) 0 0 0 0.035(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(6) 0.74(3) 0 0 0 0.131(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(8) 0.74(4) 0 0 0 0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(9) 0.69(4) 0 0 0 0.091(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(10) 0.84(3) 0 0 0 0.087(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 ZN(1) N(1) Z ZN(1) N(2) Y CL(1) C(2) Z CL(1) C(1) Y CL(2) C(7) Z CL(2) C(8) Y CL(3) ZN(1) Z CL(3) H(1) Y CL(4) ZN(1) Z CL(4) H(10) Y N(1) C(1) Z N(1) C(5) Y N(2) C(6) Z N(2) C(10) Y C(1) H(1) Z C(1) N(1) Y C(2) C(1) Z C(2) C(3) Y C(3) H(3) Z C(3) C(4) Y C(4) H(4) Z C(4) C(3) Y C(5) H(5) Z C(5) N(1) Y C(6) H(6) Z C(6) N(2) Y C(7) C(8) Z C(7) C(6) Y C(8) H(8) Z C(8) C(7) Y C(9) H(9) Z C(9) C(8) Y C(10) H(10) Z C(10) N(2) Y H(1) C(1) Z H(1) N(1) Y H(3) C(3) Z H(3) C(4) Y H(4) C(4) Z H(4) C(3) Y H(5) C(5) Z H(5) N(1) Y H(6) C(6) Z H(6) N(2) Y H(8) C(8) Z H(8) C(7) Y H(9) C(9) Z H(9) C(8) Y H(10) C(10) Z H(10) N(2) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CL(1) C(2) 1.7218(5) 1_555 1_555 yes CL(2) C(7) 1.7199(5) 1_555 1_555 yes N(1) C(1) 1.3453(7) 1_555 1_555 yes N(1) C(5) 1.3475(6) 1_555 1_555 yes N(2) C(6) 1.3434(7) 1_555 1_555 yes N(2) C(10) 1.3443(7) 1_555 1_555 yes C(1) C(2) 1.3869(7) 1_555 1_555 yes C(2) C(3) 1.3930(7) 1_555 1_555 yes C(3) C(4) 1.3898(8) 1_555 1_555 yes C(4) C(5) 1.3886(7) 1_555 1_555 yes C(6) C(7) 1.3918(7) 1_555 1_555 yes C(7) C(8) 1.3874(8) 1_555 1_555 yes C(8) C(9) 1.3890(8) 1_555 1_555 yes C(9) C(10) 1.3887(8) 1_555 1_555 yes H(1) C(1) 1.083 1_555 1_555 yes H(3) C(3) 1.083 1_555 1_555 yes H(4) C(4) 1.083 1_555 1_555 yes H(5) C(5) 1.083 1_555 1_555 yes H(6) C(6) 1.083 1_555 1_555 yes H(8) C(8) 1.083 1_555 1_555 yes H(9) C(9) 1.083 1_555 1_555 yes H(10) C(10) 1.083 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) N(1) C(5) 119.56(5) 1_555 1_555 1_555 yes C(6) N(2) C(10) 119.26(5) 1_555 1_555 1_555 yes N(1) C(1) C(2) 120.88(5) 1_555 1_555 1_555 yes CL(1) C(2) C(1) 118.72(4) 1_555 1_555 1_555 yes CL(1) C(2) C(3) 120.95(4) 1_555 1_555 1_555 yes C(1) C(2) C(3) 120.31(5) 1_555 1_555 1_555 yes C(2) C(3) C(4) 118.07(5) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.15(5) 1_555 1_555 1_555 yes N(1) C(5) C(4) 122.01(5) 1_555 1_555 1_555 yes N(2) C(6) C(7) 120.85(5) 1_555 1_555 1_555 yes CL(2) C(7) C(6) 119.80(4) 1_555 1_555 1_555 yes CL(2) C(7) C(8) 119.79(4) 1_555 1_555 1_555 yes C(6) C(7) C(8) 120.41(5) 1_555 1_555 1_555 yes C(7) C(8) C(9) 118.05(5) 1_555 1_555 1_555 yes C(8) C(9) C(10) 118.97(5) 1_555 1_555 1_555 yes N(2) C(10) C(9) 122.42(5) 1_555 1_555 1_555 yes N(1) C(1) H(1) 119.54 1_555 1_555 1_555 yes C(2) C(1) H(1) 119.59 1_555 1_555 1_555 yes C(2) C(3) H(3) 120.96 1_555 1_555 1_555 yes C(4) C(3) H(3) 120.97 1_555 1_555 1_555 yes C(3) C(4) H(4) 120.35 1_555 1_555 1_555 yes N(1) C(5) H(5) 118.98 1_555 1_555 1_555 yes N(2) C(6) H(6) 119.61 1_555 1_555 1_555 yes C(7) C(8) H(8) 120.99 1_555 1_555 1_555 yes C(8) C(9) H(9) 120.51 1_555 1_555 1_555 yes C(9) C(10) H(10) 118.75 1_555 1_555 1_555 yes _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 45.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.680 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.139