#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013845.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013845 loop_ _publ_author_name 'Zachara, Janusz' 'Madura, Izabela' 'W\/lostowski, Marek' _publ_section_title ; Hydrogen-bonding patterns in two structural isomers of 3,6-bis(2-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o57 _journal_page_last o59 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H10 Cl2 N4' _chemical_formula_moiety 'C14 H10 Cl2 N4' _chemical_formula_structural 'C2 H2 N4( C6H4Cl)2' _chemical_formula_sum 'C14 H10 Cl2 N4' _chemical_formula_weight 305.16 _chemical_name_systematic ; 3,6-bis(2-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 121.664(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 16.0020(12) _cell_length_b 9.4123(8) _cell_length_c 10.5752(7) _cell_measurement_reflns_used 30 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.41 _cell_measurement_theta_min 7.66 _cell_volume 1355.69(19) _computing_cell_refinement 'P3/P4-PC Software' _computing_data_collection 'P3/P4-PC Software (Siemens, 1991)' _computing_data_reduction 'XDISK (Siemens, 1991)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens, P3' _diffrn_measurement_method 'profile data from \w--2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2496 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.63 _diffrn_standards_decay_% 1.8 _diffrn_standards_interval_count 70 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_T_max 0.9602 _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SHELX76 (Sheldrick, 1976)' _exptl_crystal_colour yellow--orange _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.391 _refine_diff_density_min -0.428 _refine_ls_extinction_coef 0.0047(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 1203 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0357 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.4393P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.0985 _reflns_number_gt 996 _reflns_number_total 1203 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1670.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 1355.69(18) _cod_database_code 2013845 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' loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.16401(5) 0.74870(6) 0.21918(8) 0.0646(3) Uani d . 1 . . Cl N1 0.04530(12) 0.4499(2) 0.18150(18) 0.0376(4) Uani d . 1 . . N N2 0.05456(12) 0.49908(19) 0.40415(17) 0.0372(4) Uani d . 1 . . N C1 0.20247(14) 0.5248(2) 0.4027(2) 0.0359(5) Uani d . 1 . . C C2 0.24122(16) 0.6321(2) 0.3587(2) 0.0439(5) Uani d . 1 . . C C3 0.3429(2) 0.6493(3) 0.4296(3) 0.0618(8) Uani d . 1 . . C C4 0.4044(2) 0.5597(4) 0.5428(3) 0.0646(8) Uani d . 1 . . C C5 0.36748(18) 0.4549(3) 0.5887(3) 0.0589(7) Uani d . 1 . . C C6 0.26745(15) 0.4384(3) 0.5202(2) 0.0434(5) Uani d . 1 . . C C10 0.09617(14) 0.4949(2) 0.3295(2) 0.0334(5) Uani d . 1 . . C H1 0.0749(15) 0.470(2) 0.134(2) 0.036(5) Uiso d . 1 . . H H3 0.362(2) 0.720(3) 0.398(3) 0.072(9) Uiso d . 1 . . H H4 0.475(2) 0.568(4) 0.593(3) 0.094(10) Uiso d . 1 . . H H5 0.412(2) 0.391(3) 0.670(3) 0.078(9) Uiso d . 1 . . H H6 0.2407(16) 0.363(3) 0.552(2) 0.049(6) Uiso d . 1 . . H 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 Cl1 0.0958(6) 0.0467(4) 0.0745(5) 0.0089(3) 0.0608(4) 0.0122(3) N1 0.0339(9) 0.0530(11) 0.0309(9) 0.0034(8) 0.0204(8) -0.0022(8) N2 0.0340(9) 0.0513(10) 0.0298(8) -0.0032(7) 0.0191(7) 0.0000(7) C1 0.0388(11) 0.0407(11) 0.0350(10) -0.0041(9) 0.0242(9) -0.0080(8) C2 0.0558(13) 0.0434(12) 0.0480(12) -0.0080(10) 0.0380(11) -0.0100(10) C3 0.0720(18) 0.0631(16) 0.0756(18) -0.0309(15) 0.0560(16) -0.0241(15) C4 0.0409(14) 0.091(2) 0.0577(16) -0.0135(14) 0.0232(13) -0.0206(15) C5 0.0424(13) 0.0792(19) 0.0461(13) -0.0030(13) 0.0172(11) -0.0095(13) C6 0.0378(12) 0.0531(14) 0.0372(11) -0.0024(10) 0.0181(10) -0.0040(10) C10 0.0370(11) 0.0366(10) 0.0309(10) -0.0004(8) 0.0208(9) 0.0004(8) 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 Cl1 C2 . 1.730(2) yes N1 C10 . 1.398(2) yes N1 N2 2 1.438(2) yes N1 H1 . 0.88(2) no N2 C10 . 1.273(2) yes N2 N1 2 1.438(2) no C10 C1 . 1.480(3) yes C1 C2 . 1.388(3) no C1 C6 . 1.389(3) no C2 C3 . 1.399(3) no C3 C4 . 1.369(4) no C3 H3 . 0.87(3) no C4 C5 . 1.363(4) no C4 H4 . 0.97(3) no C5 C6 . 1.376(3) no C5 H5 . 0.98(3) no C6 H6 . 0.98(2) no 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' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 -2 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 C10 N1 N2 . 2 114.14(15) yes C10 N1 H1 . . 114.1(14) no N2 N1 H1 2 . 109.0(13) no C10 N2 N1 . 2 111.68(16) yes N2 C10 N1 . . 121.13(18) yes N2 C10 C1 . . 120.07(17) yes N1 C10 C1 . . 118.55(16) yes C2 C1 C6 . . 118.02(19) no C2 C1 C10 . . 123.78(19) yes C6 C1 C10 . . 118.17(18) yes C1 C2 C3 . . 120.2(2) no C1 C2 Cl1 . . 120.20(17) yes C3 C2 Cl1 . . 119.56(19) yes C4 C3 C2 . . 119.8(3) no C4 C3 H3 . . 125(2) no C2 C3 H3 . . 115(2) no C5 C4 C3 . . 120.7(2) no C5 C4 H4 . . 117(2) no C3 C4 H4 . . 122(2) no C4 C5 C6 . . 119.7(3) no C4 C5 H5 . . 120.6(17) no C6 C5 H5 . . 119.7(17) no C5 C6 C1 . . 121.5(2) no C5 C6 H6 . . 120.0(13) no C1 C6 H6 . . 118.4(13) no 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 N2 6_565 0.88(2) 2.29(2) 3.052(2) 145(2) yes C6 H6 Cl1 6_566 0.98(2) 2.83(2) 3.732(2) 154(2) yes 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 _geom_torsion_publ_flag N1 N2 C10 N1 2 1.4(3) yes N1 N2 C10 C1 2 -172.72(17) yes N2 N1 C10 N2 2 39.8(2) yes N2 N1 C10 C1 2 -146.05(18) yes N2 C10 C1 C2 . -121.8(2) n N1 C10 C1 C2 . 63.9(3) n N2 C10 C1 C6 . 59.8(3) n N1 C10 C1 C6 . -114.4(2) n C6 C1 C2 C3 . 1.3(3) ? C10 C1 C2 C3 . -177.05(19) ? C6 C1 C2 Cl1 . -176.82(16) ? C10 C1 C2 Cl1 . 4.8(3) ? C1 C2 C3 C4 . 0.0(4) ? Cl1 C2 C3 C4 . 178.2(2) ? C2 C3 C4 C5 . -0.9(4) ? C3 C4 C5 C6 . 0.2(4) ? C4 C5 C6 C1 . 1.2(4) ? C2 C1 C6 C5 . -2.0(3) ? C10 C1 C6 C5 . 176.5(2) ? _cod_database_fobs_code 2013845 _journal_paper_doi 10.1107/S0108270103026945