#------------------------------------------------------------------------------ #$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/54/2215457.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_2215457 loop_ _publ_author_name 'Zhang, Chun-Xia' 'Yin, Zhi-Gang' 'Qian, Heng-Yu' 'Hu, Jie' 'Feng, Yu-Li' _publ_section_title ; 3-Bromo-4-methoxybenzaldehyde 4-nitrophenylhydrazone ; _journal_coeditor_code DN3064 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4165 _journal_page_last o4165 _journal_paper_doi 10.1107/S1600536807046533 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C14 H12 Br N3 O3' _chemical_formula_moiety 'C14 H12 Br N3 O3' _chemical_formula_sum 'C14 H12 Br N3 O3' _chemical_formula_weight 350.18 _chemical_name_systematic ; 3-Bromo-4-methoxybenzaldehyde 4-nitrophenylhydrazone ; _space_group_IT_number 56 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.2800(15) _cell_length_b 14.678(3) _cell_length_c 27.368(6) _cell_measurement_reflns_used 1248 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.8 _cell_measurement_theta_min 2.5 _cell_volume 2924.4(11) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 30041 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 2.78 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.824 _exptl_absorpt_correction_T_max 0.548 _exptl_absorpt_correction_T_min 0.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1408 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.931 _refine_diff_density_min -0.581 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2980 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.217 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0911 _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^)+(0.045P)^2^+6.3175P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1661 _refine_ls_wR_factor_ref 0.1756 _reflns_number_gt 2456 _reflns_number_total 2980 _reflns_threshold_expression I>2\s(I) _cod_data_source_file dn3064.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2924.4(10) _cod_database_code 2215457 _cod_database_fobs_code 2215457 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, 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 0.11817(15) 0.97770(5) 0.17684(2) 0.1058(4) Uani d . 1 O O1 0.3606(7) 1.1359(3) 0.58357(17) 0.0930(14) Uani d . 1 O O2 0.4495(6) 1.2106(3) 0.51958(19) 0.0857(13) Uani d . 1 O O3 0.0204(7) 0.7930(3) 0.14235(15) 0.0887(14) Uani d . 1 N N1 0.3772(7) 1.1431(3) 0.5392(2) 0.0687(13) Uani d . 1 N N2 0.1160(7) 0.8638(3) 0.42050(15) 0.0642(12) Uani d . 1 H H2 0.0786 0.8142 0.4340 0.077 Uiso calc R 1 N N3 0.1076(6) 0.8735(3) 0.37049(16) 0.0630(12) Uani d . 1 C C1 0.3092(7) 1.0709(4) 0.50809(19) 0.0556(13) Uani d . 1 C C2 0.2439(8) 0.9916(4) 0.5293(2) 0.0602(13) Uani d . 1 H H2A 0.2421 0.9849 0.5630 0.072 Uiso calc R 1 C C3 0.1816(7) 0.9227(4) 0.49932(18) 0.0573(13) Uani d . 1 H H3 0.1378 0.8690 0.5131 0.069 Uiso calc R 1 C C4 0.1836(7) 0.9327(3) 0.44878(18) 0.0509(12) Uani d . 1 C C5 0.2542(8) 1.0125(4) 0.42843(19) 0.0591(13) Uani d . 1 H H5 0.2577 1.0196 0.3947 0.071 Uiso calc R 1 C C6 0.3184(8) 1.0802(4) 0.4581(2) 0.0615(14) Uani d . 1 H H6 0.3683 1.1328 0.4445 0.074 Uiso calc R 1 C C7 0.0422(8) 0.8060(4) 0.3473(2) 0.0666(15) Uani d . 1 H H7 0.0015 0.7557 0.3648 0.080 Uiso calc R 1 C C8 0.0284(8) 0.8046(4) 0.2942(2) 0.0622(14) Uani d . 1 C C9 0.0654(8) 0.8806(4) 0.2657(2) 0.0621(14) Uani d . 1 H H9 0.0943 0.9358 0.2805 0.075 Uiso calc R 1 C C10 0.0594(8) 0.8745(4) 0.2153(2) 0.0648(15) Uani d . 1 C C11 0.0189(8) 0.7920(4) 0.1923(2) 0.0656(15) Uani d . 1 C C12 -0.0173(9) 0.7173(4) 0.2203(3) 0.0802(19) Uani d . 1 H H12 -0.0449 0.6620 0.2055 0.096 Uiso calc R 1 C C13 -0.0130(9) 0.7237(4) 0.2705(2) 0.0745(17) Uani d . 1 H H13 -0.0388 0.6722 0.2891 0.089 Uiso calc R 1 C C14 -0.0039(13) 0.7075(5) 0.1180(3) 0.112(3) Uani d . 1 H H14A 0.0900 0.6658 0.1284 0.167 Uiso calc R 1 H H14B 0.0044 0.7163 0.0833 0.167 Uiso calc R 1 H H14C -0.1224 0.6830 0.1260 0.167 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 0.1924(10) 0.0635(4) 0.0616(4) 0.0057(5) -0.0070(5) -0.0025(3) O1 0.119(4) 0.090(3) 0.069(3) -0.005(3) -0.008(3) -0.017(2) O2 0.091(3) 0.057(2) 0.108(3) -0.012(2) -0.009(3) -0.005(2) O3 0.126(4) 0.075(3) 0.064(2) 0.023(3) -0.029(3) -0.030(2) N1 0.063(3) 0.061(3) 0.082(4) 0.008(3) -0.007(3) -0.009(3) N2 0.082(3) 0.059(3) 0.052(2) -0.010(3) -0.002(2) 0.008(2) N3 0.071(3) 0.067(3) 0.051(2) -0.003(2) -0.003(2) 0.002(2) C1 0.053(3) 0.052(3) 0.062(3) 0.006(2) -0.011(3) -0.002(2) C2 0.063(3) 0.066(3) 0.052(3) 0.009(3) -0.001(3) 0.006(3) C3 0.062(3) 0.054(3) 0.055(3) 0.000(3) -0.003(3) 0.009(2) C4 0.045(3) 0.053(3) 0.055(3) 0.002(2) -0.003(2) 0.002(2) C5 0.066(3) 0.060(3) 0.050(3) -0.009(3) -0.003(3) 0.009(2) C6 0.062(3) 0.050(3) 0.072(4) -0.003(3) -0.004(3) 0.014(3) C7 0.071(4) 0.057(3) 0.071(4) -0.006(3) -0.010(3) -0.002(3) C8 0.056(3) 0.065(4) 0.065(3) -0.004(3) -0.007(3) -0.010(3) C9 0.075(4) 0.053(3) 0.059(3) 0.006(3) -0.015(3) -0.012(3) C10 0.083(4) 0.052(3) 0.060(3) 0.016(3) -0.013(3) -0.012(3) C11 0.065(4) 0.066(4) 0.066(3) 0.014(3) -0.019(3) -0.019(3) C12 0.088(5) 0.055(3) 0.098(5) -0.005(3) -0.023(4) -0.028(3) C13 0.083(4) 0.062(4) 0.078(4) -0.010(3) -0.012(3) -0.004(3) C14 0.161(8) 0.086(5) 0.088(5) 0.034(5) -0.040(5) -0.044(4) 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 C11 O3 C14 117.0(5) O1 N1 O2 122.5(5) O1 N1 C1 119.1(5) O2 N1 C1 118.4(5) C4 N2 N3 120.3(4) C4 N2 H2 119.9 N3 N2 H2 119.9 C7 N3 N2 115.7(5) C6 C1 C2 121.1(5) C6 C1 N1 119.7(5) C2 C1 N1 119.2(5) C3 C2 C1 118.8(5) C3 C2 H2A 120.6 C1 C2 H2A 120.6 C2 C3 C4 120.7(5) C2 C3 H3 119.7 C4 C3 H3 119.7 N2 C4 C3 118.8(5) N2 C4 C5 121.9(5) C3 C4 C5 119.3(5) C6 C5 C4 120.0(5) C6 C5 H5 120.0 C4 C5 H5 120.0 C5 C6 C1 120.2(5) C5 C6 H6 119.9 C1 C6 H6 119.9 N3 C7 C8 122.5(5) N3 C7 H7 118.8 C8 C7 H7 118.8 C13 C8 C9 117.8(5) C13 C8 C7 119.6(6) C9 C8 C7 122.4(5) C10 C9 C8 120.2(5) C10 C9 H9 119.9 C8 C9 H9 119.9 C9 C10 C11 120.8(6) C9 C10 Br1 119.7(4) C11 C10 Br1 119.4(4) C12 C11 O3 125.0(5) C12 C11 C10 118.9(5) O3 C11 C10 116.1(6) C11 C12 C13 120.1(5) C11 C12 H12 119.9 C13 C12 H12 119.9 C12 C13 C8 122.0(6) C12 C13 H13 119.0 C8 C13 H13 119.0 O3 C14 H14A 109.5 O3 C14 H14B 109.5 H14A C14 H14B 109.5 O3 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C10 1.893(6) O1 N1 1.226(6) O2 N1 1.244(6) O3 C11 1.367(7) O3 C14 1.432(7) N1 C1 1.447(7) N2 C4 1.364(6) N2 N3 1.377(6) N2 H2 0.8600 N3 C7 1.269(7) C1 C6 1.376(7) C1 C2 1.384(7) C2 C3 1.379(7) C2 H2A 0.9300 C3 C4 1.391(7) C3 H3 0.9300 C4 C5 1.396(7) C5 C6 1.366(7) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.456(8) C7 H7 0.9300 C8 C13 1.385(8) C8 C9 1.389(8) C9 C10 1.382(7) C9 H9 0.9300 C10 C11 1.398(7) C11 C12 1.363(9) C12 C13 1.379(9) C12 H12 0.9300 C13 H13 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 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 N2 H2 O2 6_556 0.86 2.19 3.035(6) 166.1 C7 H7 O1 6_556 0.93 2.48 3.400(8) 172.0