#------------------------------------------------------------------------------ #$Date: 2017-10-13 09:03:29 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214562.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_2214562 loop_ _publ_author_name 'Huan-Mei Guo' _publ_section_title ; N'-(4-Bromobenzylidene)propanohydrazide ; _journal_coeditor_code BX2094 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3461 _journal_page_last o3461 _journal_paper_doi 10.1107/S1600536807032989 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C10 H11 Br N2 O' _chemical_formula_moiety 'C10 H11 Br N2 O' _chemical_formula_sum 'C10 H11 Br N2 O' _chemical_formula_weight 255.12 _chemical_name_systematic ; N'-(4-Bromobenzylidene)propanohydrazide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.514(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.7749(10) _cell_length_b 10.253(2) _cell_length_c 22.183(4) _cell_measurement_temperature 294(2) _cell_measurement_theta_max 25.01 _cell_measurement_theta_min 1.84 _cell_volume 1081.0(4) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area-detector' _diffrn_measurement_method 'phi and omega 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 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 5443 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.84 _exptl_absorpt_coefficient_mu 3.772 _exptl_absorpt_correction_T_max 0.6203 _exptl_absorpt_correction_T_min 0.4181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.413 _refine_diff_density_min -0.343 _refine_ls_extinction_coef 0.0194(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1906 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 0.997 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0412P)^2^+0.4567P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.0866 _reflns_number_gt 1363 _reflns_number_total 1906 _reflns_threshold_expression >2sigma(I) _cod_data_source_file bx2094.cif _cod_data_source_block I _cod_original_sg_symbol_Hall '-P 2yn ' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2214562 _cod_database_fobs_code 2214562 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 Br Br1 0.77061(8) 0.21453(4) 0.196101(18) 0.0605(2) Uani d . 1 N N1 -0.0531(6) 0.1549(3) 0.43391(13) 0.0441(7) Uani d . 1 O O1 -0.4993(5) 0.1484(3) 0.54910(11) 0.0573(7) Uani d . 1 N N2 -0.2420(6) 0.1110(3) 0.47212(13) 0.0471(8) Uani d . 1 H H2 -0.3080 0.0331 0.4679 0.057 Uiso calc R 1 C C1 0.3146(7) 0.2337(3) 0.34522(16) 0.0465(9) Uani d . 1 H H1 0.2713 0.2969 0.3729 0.056 Uiso calc R 1 C C2 0.4859(8) 0.2653(4) 0.30103(17) 0.0477(9) Uani d . 1 H H2A 0.5590 0.3491 0.2989 0.057 Uiso calc R 1 C C3 0.5480(7) 0.1711(4) 0.25989(15) 0.0429(9) Uani d . 1 C C4 0.4499(7) 0.0465(4) 0.26351(17) 0.0500(9) Uani d . 1 H H4 0.4975 -0.0166 0.2362 0.060 Uiso calc R 1 C C5 0.2792(7) 0.0152(4) 0.30818(16) 0.0501(10) Uani d . 1 H H5 0.2130 -0.0697 0.3109 0.060 Uiso calc R 1 C C6 0.2049(7) 0.1087(3) 0.34909(14) 0.0396(8) Uani d . 1 C C7 0.0139(7) 0.0733(3) 0.39412(15) 0.0427(8) Uani d . 1 H H7 -0.0606 -0.0105 0.3938 0.051 Uiso calc R 1 C C8 -0.3254(7) 0.1882(3) 0.51608(16) 0.0446(9) Uani d . 1 C C9 -0.1936(9) 0.3205(4) 0.5226(2) 0.0647(12) Uani d . 1 H H9A -0.2210 0.3649 0.4839 0.078 Uiso calc R 1 H H9B 0.0074 0.3101 0.5327 0.078 Uiso calc R 1 C C10 -0.3091(10) 0.4053(4) 0.5702(2) 0.0781(14) Uani d U 1 H H10A -0.2727 0.3648 0.6092 0.117 Uiso calc R 1 H H10B -0.5083 0.4158 0.5608 0.117 Uiso calc R 1 H H10C -0.2195 0.4892 0.5708 0.117 Uiso calc R 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 Br1 0.0552(3) 0.0728(4) 0.0571(3) -0.0027(2) 0.02439(19) 0.0049(2) N1 0.0437(16) 0.0492(18) 0.0415(17) -0.0020(14) 0.0153(14) 0.0055(14) O1 0.0602(16) 0.0590(17) 0.0574(16) -0.0039(14) 0.0288(14) 0.0030(13) N2 0.0523(17) 0.0448(19) 0.0473(17) -0.0056(14) 0.0199(15) 0.0033(14) C1 0.052(2) 0.042(2) 0.046(2) 0.0005(17) 0.0097(17) -0.0070(17) C2 0.053(2) 0.039(2) 0.053(2) -0.0070(17) 0.0108(18) -0.0007(17) C3 0.0373(18) 0.051(2) 0.041(2) 0.0030(16) 0.0108(16) 0.0058(16) C4 0.056(2) 0.041(2) 0.056(2) 0.0054(18) 0.0200(18) -0.0042(18) C5 0.053(2) 0.038(2) 0.062(2) -0.0045(17) 0.0194(19) -0.0004(18) C6 0.0382(18) 0.042(2) 0.0391(19) 0.0023(16) 0.0053(15) 0.0014(16) C7 0.0431(19) 0.041(2) 0.045(2) -0.0002(16) 0.0081(16) 0.0037(16) C8 0.045(2) 0.047(2) 0.043(2) 0.0059(16) 0.0118(17) 0.0063(17) C9 0.074(3) 0.053(3) 0.072(3) -0.006(2) 0.033(2) -0.007(2) C10 0.083(3) 0.069(3) 0.087(3) -0.006(2) 0.030(3) -0.019(2) 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' Br Br -0.2901 2.4595 '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 115.8(3) C8 N2 N1 120.8(3) C8 N2 H2 119.6 N1 N2 H2 119.6 C2 C1 C6 121.0(3) C2 C1 H1 119.5 C6 C1 H1 119.5 C1 C2 C3 119.1(3) C1 C2 H2A 120.4 C3 C2 H2A 120.4 C4 C3 C2 121.3(3) C4 C3 Br1 118.8(3) C2 C3 Br1 119.9(3) C3 C4 C5 119.3(3) C3 C4 H4 120.4 C5 C4 H4 120.4 C4 C5 C6 121.0(3) C4 C5 H5 119.5 C6 C5 H5 119.5 C5 C6 C1 118.3(3) C5 C6 C7 119.4(3) C1 C6 C7 122.3(3) N1 C7 C6 121.6(3) N1 C7 H7 119.2 C6 C7 H7 119.2 O1 C8 N2 120.1(3) O1 C8 C9 123.0(3) N2 C8 C9 116.9(3) C8 C9 C10 114.3(3) C8 C9 H9A 108.7 C10 C9 H9A 108.7 C8 C9 H9B 108.7 C10 C9 H9B 108.7 H9A C9 H9B 107.6 C9 C10 H10A 109.5 C9 C10 H10B 109.5 H10A C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C3 1.903(3) N1 C7 1.279(4) N1 N2 1.372(3) O1 C8 1.228(4) N2 C8 1.346(4) N2 H2 0.8600 C1 C2 1.374(5) C1 C6 1.391(5) C1 H1 0.9300 C2 C3 1.381(5) C2 H2A 0.9300 C3 C4 1.366(5) C4 C5 1.380(4) C4 H4 0.9300 C5 C6 1.389(5) C5 H5 0.9300 C6 C7 1.462(4) C7 H7 0.9300 C8 C9 1.497(5) C9 C10 1.513(5) C9 H9A 0.9700 C9 H9B 0.9700 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 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 N2 H2 O1 3_456 0.86 2.09 2.951(4) 174.0 y 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 C7 N1 N2 C8 179.4(3) C6 C1 C2 C3 0.3(5) C1 C2 C3 C4 -2.1(5) C1 C2 C3 Br1 177.2(3) C2 C3 C4 C5 1.8(6) Br1 C3 C4 C5 -177.5(3) C3 C4 C5 C6 0.4(5) C4 C5 C6 C1 -2.1(5) C4 C5 C6 C7 177.4(3) C2 C1 C6 C5 1.8(5) C2 C1 C6 C7 -177.7(3) N2 N1 C7 C6 177.7(3) C5 C6 C7 N1 177.7(3) C1 C6 C7 N1 -2.8(5) N1 N2 C8 O1 178.4(3) N1 N2 C8 C9 -2.5(5) O1 C8 C9 C10 -4.5(6) N2 C8 C9 C10 176.5(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655288