#------------------------------------------------------------------------------ #$Date: 2012-02-28 14:14:52 +0200 (Tue, 28 Feb 2012) $ #$Revision: 35911 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/30/8103089.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8103089 loop_ _publ_author_name 'Yu-Mei Hao' _publ_section_title ; Crystal structure of 2-chloro-N'-(2-methoxy- benzylidene)benzohydrazide, C15H13ClN2O2 ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 11 _journal_volume 226 _journal_year 2011 _chemical_formula_moiety 'C15 H13 Cl N2 O2' _chemical_formula_sum 'C15 H13 Cl N2 O2' _chemical_formula_weight 288.72 _chemical_name_systematic ; 2-chloro-N'-(2-methoxybenzylidene)benzohydrazide, C~15~H~13~ClN~2~O~2~ ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 107.587(2) _cell_angle_beta 95.724(2) _cell_angle_gamma 93.646(2) _cell_formula_units_Z 2 _cell_length_a 4.9555(10) _cell_length_b 11.540(2) _cell_length_c 12.782(3) _cell_measurement_reflns_used 1637 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.9 _cell_measurement_theta_min 2.8 _cell_volume 689.9(2) _computing_cell_refinement SAINT _computing_data_collection SMART _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-97 [12]' _computing_structure_solution 'SHELXS-97 [11]' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w 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 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5636 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.87 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_T_max 0.9411 _exptl_absorpt_correction_T_min 0.9285 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.207 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2938 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0446 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.1470P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1036 _refine_ls_wR_factor_ref 0.1171 _reflns_number_gt 2108 _reflns_number_total 2938 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file 1267-3274.cff _[local]_cod_data_source_block 3 _[local]_cod_cif_authors_sg_H-M P-1 _cod_database_code 8103089 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Cl1 Cl 0.15282(12) 0.10504(5) 0.18460(5) 0.0683(2) Uani 1 1 d . N1 N 0.7114(3) 0.23267(14) 0.54843(12) 0.0400(4) Uani 1 1 d . N2 N 0.7138(3) 0.14238(14) 0.44823(12) 0.0377(4) Uani 1 1 d D O1 O 1.2923(3) 0.50687(12) 0.62340(11) 0.0538(4) Uani 1 1 d . O2 O 0.2582(3) 0.09558(15) 0.42657(13) 0.0648(5) Uani 1 1 d . C1 C 0.9525(4) 0.40440(17) 0.68648(15) 0.0396(4) Uani 1 1 d . C2 C 1.1427(4) 0.50600(17) 0.70730(16) 0.0422(5) Uani 1 1 d . C3 C 1.1670(4) 0.59913(19) 0.80742(18) 0.0536(6) Uani 1 1 d . H3 H 1.2938 0.6666 0.8212 0.064 Uiso 1 1 calc R C4 C 1.0030(5) 0.5914(2) 0.88614(18) 0.0616(6) Uani 1 1 d . H4 H 1.0220 0.6532 0.9536 0.074 Uiso 1 1 calc R C5 C 0.8110(5) 0.4933(2) 0.86644(18) 0.0601(6) Uani 1 1 d . H5 H 0.6984 0.4897 0.9196 0.072 Uiso 1 1 calc R C6 C 0.7869(4) 0.4005(2) 0.76726(17) 0.0491(5) Uani 1 1 d . H6 H 0.6575 0.3340 0.7542 0.059 Uiso 1 1 calc R C7 C 0.9284(4) 0.30562(16) 0.58161(15) 0.0402(4) Uani 1 1 d . H7 H 1.0718 0.2960 0.5390 0.048 Uiso 1 1 calc R C8 C 0.4791(3) 0.07936(16) 0.39254(15) 0.0384(4) Uani 1 1 d . C9 C 0.5115(3) -0.01092(16) 0.28395(15) 0.0364(4) Uani 1 1 d . C10 C 0.3678(4) -0.00883(17) 0.18539(16) 0.0432(5) Uani 1 1 d . C11 C 0.3972(4) -0.0929(2) 0.08549(17) 0.0539(6) Uani 1 1 d . H11 H 0.2988 -0.0901 0.0206 0.065 Uiso 1 1 calc R C12 C 0.5733(5) -0.1809(2) 0.08258(19) 0.0593(6) Uani 1 1 d . H12 H 0.5940 -0.2380 0.0155 0.071 Uiso 1 1 calc R C13 C 0.7184(4) -0.18469(19) 0.17851(19) 0.0549(6) Uani 1 1 d . H13 H 0.8377 -0.2442 0.1761 0.066 Uiso 1 1 calc R C14 C 0.6883(4) -0.10056(17) 0.27848(17) 0.0452(5) Uani 1 1 d . H14 H 0.7877 -0.1040 0.3430 0.054 Uiso 1 1 calc R C15 C 1.4823(5) 0.6103(2) 0.6398(2) 0.0628(6) Uani 1 1 d . H15A H 1.3886 0.6827 0.6547 0.094 Uiso 1 1 calc R H15B H 1.5696 0.6009 0.5743 0.094 Uiso 1 1 calc R H15C H 1.6172 0.6170 0.7012 0.094 Uiso 1 1 calc R H2 H 0.875(3) 0.130(2) 0.423(2) 0.080 Uiso 1 1 d 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 Cl1 0.0609(4) 0.0619(4) 0.0776(4) 0.0205(3) -0.0147(3) 0.0165(3) N1 0.0325(8) 0.0428(8) 0.0403(9) 0.0067(7) 0.0040(7) 0.0044(7) N2 0.0258(8) 0.0412(8) 0.0405(9) 0.0048(7) 0.0044(6) 0.0025(6) O1 0.0495(9) 0.0527(8) 0.0510(9) 0.0074(7) 0.0052(7) -0.0099(7) O2 0.0244(7) 0.0876(11) 0.0627(10) -0.0065(8) 0.0081(7) 0.0041(7) C1 0.0333(10) 0.0454(10) 0.0388(10) 0.0118(8) 0.0001(8) 0.0077(8) C2 0.0346(10) 0.0471(10) 0.0417(11) 0.0103(9) -0.0006(8) 0.0063(8) C3 0.0462(12) 0.0515(12) 0.0513(13) 0.0027(10) -0.0071(10) 0.0034(10) C4 0.0565(14) 0.0704(15) 0.0427(13) -0.0044(11) -0.0020(11) 0.0152(12) C5 0.0534(13) 0.0829(17) 0.0423(12) 0.0137(12) 0.0099(10) 0.0164(12) C6 0.0417(11) 0.0592(12) 0.0453(12) 0.0150(10) 0.0040(9) 0.0056(9) C7 0.0345(10) 0.0415(10) 0.0416(11) 0.0085(8) 0.0057(8) 0.0028(8) C8 0.0253(9) 0.0429(10) 0.0447(11) 0.0100(8) 0.0041(8) 0.0042(7) C9 0.0260(9) 0.0386(9) 0.0416(10) 0.0092(8) 0.0038(8) -0.0017(7) C10 0.0323(10) 0.0441(10) 0.0497(12) 0.0126(9) -0.0017(8) -0.0014(8) C11 0.0521(13) 0.0611(13) 0.0413(12) 0.0099(10) -0.0037(10) -0.0038(10) C12 0.0602(14) 0.0562(13) 0.0489(13) -0.0019(10) 0.0088(11) 0.0019(11) C13 0.0490(12) 0.0473(12) 0.0637(15) 0.0072(10) 0.0124(11) 0.0120(9) C14 0.0381(11) 0.0486(11) 0.0488(12) 0.0150(9) 0.0044(9) 0.0058(9) C15 0.0639(15) 0.0559(13) 0.0679(16) 0.0238(12) 0.0009(12) -0.0111(11) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 N2 114.80(15) C8 N2 N1 119.82(14) C8 N2 H2 122.7(16) N1 N2 H2 117.5(16) C2 O1 C15 117.63(16) C6 C1 C2 118.42(18) C6 C1 C7 121.22(18) C2 C1 C7 120.35(17) O1 C2 C3 124.02(18) O1 C2 C1 115.76(16) C3 C2 C1 120.21(19) C4 C3 C2 119.8(2) C4 C3 H3 120.1 C2 C3 H3 120.1 C3 C4 C5 120.8(2) C3 C4 H4 119.6 C5 C4 H4 119.6 C4 C5 C6 119.5(2) C4 C5 H5 120.3 C6 C5 H5 120.3 C5 C6 C1 121.2(2) C5 C6 H6 119.4 C1 C6 H6 119.4 N1 C7 C1 120.19(17) N1 C7 H7 119.9 C1 C7 H7 119.9 O2 C8 N2 123.22(17) O2 C8 C9 122.91(16) N2 C8 C9 113.86(15) C14 C9 C10 117.68(17) C14 C9 C8 120.45(17) C10 C9 C8 121.86(16) C11 C10 C9 121.61(18) C11 C10 Cl1 117.92(16) C9 C10 Cl1 120.43(15) C12 C11 C10 119.5(2) C12 C11 H11 120.3 C10 C11 H11 120.3 C13 C12 C11 120.1(2) C13 C12 H12 119.9 C11 C12 H12 119.9 C12 C13 C14 120.3(2) C12 C13 H13 119.8 C14 C13 H13 119.8 C13 C14 C9 120.81(19) C13 C14 H14 119.6 C9 C14 H14 119.6 O1 C15 H15A 109.5 O1 C15 H15B 109.5 H15A C15 H15B 109.5 O1 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C10 1.745(2) N1 C7 1.274(2) N1 N2 1.387(2) N2 C8 1.342(2) N2 H2 0.894(10) O1 C2 1.365(2) O1 C15 1.422(2) O2 C8 1.222(2) C1 C6 1.391(3) C1 C2 1.398(3) C1 C7 1.462(3) C2 C3 1.389(3) C3 C4 1.374(3) C3 H3 0.9300 C4 C5 1.375(3) C4 H4 0.9300 C5 C6 1.379(3) C5 H5 0.9300 C6 H6 0.9300 C7 H7 0.9300 C8 C9 1.493(2) C9 C14 1.388(3) C9 C10 1.392(3) C10 C11 1.378(3) C11 C12 1.376(3) C11 H11 0.9300 C12 C13 1.372(3) C12 H12 0.9300 C13 C14 1.380(3) C13 H13 0.9300 C14 H14 0.9300 C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.894(10) 1.965(14) 2.809(2) 157(2) 1_655