#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202378.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_2202378 loop_ _publ_author_name 'Zhang, Yiqun' 'Khoo, Lian Ee' 'Ng, Seik Weng' _publ_section_title ; 4-Bromo-2-(2-pyridylmethyliminomethyl)phenol ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1496 _journal_page_last o1497 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C13 H11 Br N2 O' _chemical_formula_sum 'C13 H11 Br N2 O' _chemical_formula_weight 291.15 _chemical_name_systematic ; 2-(3-Pyridylmethyliminomethyl)-4-bromophenol ; _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 92.650(10) _cell_angle_beta 93.720(10) _cell_angle_gamma 95.16(2) _cell_formula_units_Z 2 _cell_length_a 4.4740(10) _cell_length_b 9.529(2) _cell_length_c 14.271(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12.7 _cell_measurement_theta_min 4.5 _cell_volume 603.8(2) _computing_cell_refinement 'LEAST SQUARES in XSCANS ' _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_data_reduction 'REDUCE in XSCANS' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.97 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measurement_device_type 'Siemens P4 four-circle diffractometer' _diffrn_measurement_method '\w-2\q scan' _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 0.030 _diffrn_reflns_av_sigmaI/netI 0.054 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 2912 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.39 _exptl_absorpt_correction_T_max 0.713 _exptl_absorpt_correction_T_min 0.531 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details ' (North et al., 1996)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.32 _refine_diff_density_min -0.28 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2069 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all 0.080 _refine_ls_R_factor_gt 0.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.2428P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.094 _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1416 _reflns_number_total 2069 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6348.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_database_code 2202378 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Br1 0.30340(10) 0.24335(6) 0.58068(3) 0.0790(3) Uani d . 1 . . Br O1 0.6041(8) 0.2028(3) 0.1768(2) 0.0710(10) Uani d . 1 . . O N1 0.9805(8) 0.4255(4) 0.2113(3) 0.0560(10) Uani d . 1 . . N N2 0.9128(9) 0.7314(4) 0.2056(3) 0.0610(10) Uani d . 1 . . N C1 0.6918(9) 0.3203(4) 0.3293(3) 0.0480(10) Uani d . 1 . . C C2 0.5480(10) 0.2130(4) 0.2681(3) 0.0520(10) Uani d . 1 . . C C3 0.3390(10) 0.1133(5) 0.3018(3) 0.0640(10) Uani d . 1 . . C C4 0.2700(10) 0.1215(5) 0.3945(4) 0.0650(10) Uani d . 1 . . C C5 0.4120(10) 0.2293(5) 0.4542(3) 0.0570(10) Uani d . 1 . . C C6 0.6200(10) 0.3267(4) 0.4223(3) 0.0530(10) Uani d . 1 . . C C7 0.9191(9) 0.4232(4) 0.2968(3) 0.0520(10) Uani d . 1 . . C C8 1.2050(10) 0.5345(5) 0.1849(3) 0.0670(10) Uani d . 1 . . C C9 1.0506(9) 0.6552(4) 0.1442(3) 0.0510(10) Uani d . 1 . . C C10 1.0500(10) 0.6829(5) 0.0507(3) 0.0660(10) Uani d . 1 . . C C11 0.9070(10) 0.7953(6) 0.0192(4) 0.080(2) Uani d . 1 . . C C12 0.7680(10) 0.8748(5) 0.0819(4) 0.077(2) Uani d . 1 . . C C13 0.7780(10) 0.8385(5) 0.1731(4) 0.0700(10) Uani d . 1 . . C H1 0.7223 0.2694 0.1649 0.106 Uiso calc R 1 . . H H3 0.2461 0.0408 0.2613 0.077 Uiso calc R 1 . . H H4 0.1296 0.0553 0.4167 0.077 Uiso calc R 1 . . H H6 0.7149 0.3978 0.4636 0.063 Uiso calc R 1 . . H H7 1.0221 0.4891 0.3401 0.063 Uiso calc R 1 . . H H8a 1.3285 0.4952 0.1388 0.080 Uiso calc R 1 . . H H8b 1.3348 0.5689 0.2398 0.080 Uiso calc R 1 . . H H10 1.1459 0.6266 0.0093 0.079 Uiso calc R 1 . . H H11 0.9041 0.8166 -0.0438 0.095 Uiso calc R 1 . . H H12 0.6697 0.9518 0.0630 0.092 Uiso calc R 1 . . H H13 0.6820 0.8931 0.2155 0.084 Uiso calc R 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 Br1 0.0971(5) 0.0796(4) 0.0632(3) 0.0097(3) 0.0178(3) 0.0149(2) O1 0.081(3) 0.067(2) 0.063(2) 0.003(2) 0.007(2) -0.010(2) N1 0.052(2) 0.051(2) 0.065(2) 0.011(2) 0.007(2) 0.011(2) N2 0.068(3) 0.059(2) 0.059(2) 0.010(2) 0.007(2) 0.006(2) C1 0.046(3) 0.043(2) 0.057(2) 0.013(2) -0.005(2) 0.003(2) C2 0.053(3) 0.048(2) 0.057(3) 0.015(2) 0.003(2) 0.001(2) C3 0.062(3) 0.049(3) 0.079(3) 0.003(2) 0.006(3) -0.010(2) C4 0.065(3) 0.047(3) 0.083(3) 0.005(2) 0.016(3) 0.009(2) C5 0.061(3) 0.056(3) 0.057(2) 0.016(2) 0.007(2) 0.011(2) C6 0.057(3) 0.049(2) 0.053(2) 0.006(2) -0.001(2) 0.001(2) C7 0.048(3) 0.045(2) 0.063(3) 0.010(2) -0.009(2) 0.004(2) C8 0.054(3) 0.065(3) 0.083(3) 0.007(2) 0.013(2) 0.015(3) C9 0.042(2) 0.052(2) 0.059(3) -0.006(2) 0.005(2) 0.009(2) C10 0.072(3) 0.060(3) 0.065(3) -0.008(3) 0.014(2) 0.002(2) C11 0.100(4) 0.076(4) 0.061(3) -0.004(3) -0.002(3) 0.019(3) C12 0.077(4) 0.056(3) 0.098(4) 0.003(3) -0.006(3) 0.025(3) C13 0.070(3) 0.056(3) 0.084(3) 0.007(3) 0.010(3) 0.002(3) 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 Br1 C5 . 1.901(4) yes O1 C2 . 1.343(5) yes N1 C7 . 1.269(5) yes N1 C8 . 1.458(6) yes N2 C9 . 1.330(5) yes N2 C13 . 1.319(6) yes C1 C2 . 1.396(6) yes C1 C6 . 1.385(6) yes C1 C7 . 1.461(6) yes C2 C3 . 1.395(6) yes C3 C4 . 1.379(6) yes C4 C5 . 1.384(6) yes C5 C6 . 1.370(6) yes C8 C9 . 1.513(6) yes C9 C10 . 1.371(6) yes C10 C11 . 1.377(7) yes C11 C12 . 1.361(8) yes C12 C13 . 1.361(7) yes O1 H1 . 0.82 no C3 H3 . 0.93 no C4 H4 . 0.93 no C6 H6 . 0.93 no C7 H7 . 0.93 no C8 H8a . 0.97 no C8 H8b . 0.97 no C10 H10 . 0.93 no C11 H11 . 0.93 no C12 H12 . 0.93 no C13 H13 . 0.93 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' 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 _geom_angle_publ_flag C7 N1 C8 118.3(4) yes C9 N2 C13 116.9(4) yes C6 C1 C2 119.1(4) yes C6 C1 C7 120.1(4) yes C2 C1 C7 120.8(4) yes O1 C2 C1 121.8(4) yes O1 C2 C3 118.5(4) yes C1 C2 C3 119.6(4) yes C2 C3 C4 120.5(4) yes C3 C4 C5 119.2(4) yes C4 C5 C6 120.8(4) yes C4 C5 Br1 118.8(3) yes C6 C5 Br1 120.4(3) yes C5 C6 C1 120.7(4) yes N1 C7 C1 122.2(4) yes N1 C8 C9 109.9(4) yes N2 C9 C8 115.0(4) yes N2 C9 C10 122.5(4) yes C10 C9 C8 122.5(4) yes C9 C10 C11 119.0(5) yes C12 C11 C10 118.7(5) yes C11 C12 C13 118.1(5) yes N2 C13 C12 124.7(5) yes C2 O1 H1 109.5 no C4 C3 H3 119.7 no C2 C3 H3 119.7 no C3 C4 H4 120.4 no C5 C4 H4 120.4 no C5 C6 H6 119.6 no C1 C6 H6 119.6 no N1 C7 H7 118.9 no C1 C7 H7 118.9 no N1 C8 H8a 109.7 no C9 C8 H8a 109.7 no N1 C8 H8b 109.7 no C9 C8 H8b 109.7 no H8a C8 H8b 108.2 no C9 C10 H10 120.5 no C11 C10 H10 120.5 no C12 C11 H11 120.6 no C10 C11 H11 120.6 no C11 C12 H12 121.0 no C13 C12 H12 121.0 no N2 C13 H13 117.6 no C12 C13 H13 117.6 no 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_publ_flag O1 H1 N1 0.82 1.87 2.595(5) 147 no 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_publ_flag C6 C1 C2 O1 178.8(4) no C7 C1 C2 O1 -2.4(6) no C6 C1 C2 C3 -1.0(6) no C7 C1 C2 C3 177.9(4) no O1 C2 C3 C4 -178.6(4) no C1 C2 C3 C4 1.2(6) no C2 C3 C4 C5 -0.4(7) no C3 C4 C5 C6 -0.5(7) no C3 C4 C5 Br1 177.8(3) no C4 C5 C6 C1 0.7(6) no Br1 C5 C6 C1 -177.5(3) no C2 C1 C6 C5 0.0(6) no C7 C1 C6 C5 -178.8(4) no C8 N1 C7 C1 178.4(3) no C6 C1 C7 N1 -176.4(4) no C2 C1 C7 N1 4.8(6) no C7 N1 C8 C9 -98.3(5) no C13 N2 C9 C10 -1.2(6) no C13 N2 C9 C8 179.4(4) no N1 C8 C9 N2 69.4(5) no N1 C8 C9 C10 -110.0(5) no N2 C9 C10 C11 1.1(7) no C8 C9 C10 C11 -179.6(4) no C9 C10 C11 C12 -0.3(8) no C10 C11 C12 C13 -0.3(8) no C9 N2 C13 C12 0.5(7) no C11 C12 C13 N2 0.2(8) no _journal_paper_doi 10.1107/S1600536803019986