#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230345.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_2230345
loop_
_publ_author_name
'Li, He-Bing'
_publ_section_title
;
 3-Bromo-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide
;
_journal_coeditor_code           HB5889
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1532
_journal_paper_doi               10.1107/S1600536811019349
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H15 Br N2 O2'
_chemical_formula_moiety         'C19 H15 Br N2 O2'
_chemical_formula_sum            'C19 H15 Br N2 O2'
_chemical_formula_weight         383.24
_chemical_name_systematic
;
3-Bromo-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 110.155(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3562(11)
_cell_length_b                   17.0404(15)
_cell_length_c                   8.6175(10)
_cell_measurement_reflns_used    1085
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1703.3(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0800
_diffrn_reflns_av_sigmaI/netI    0.1355
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9533
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.426
_exptl_absorpt_correction_T_max  0.560
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1721
_reflns_number_total             3513
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5889.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230345
_cod_database_fobs_code          2230345
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.92086(5) 0.10384(4) 0.45503(6) 0.0640(3) Uani d . 1 1 . .
N N1 0.6290(3) 0.2794(2) 0.8906(4) 0.0378(10) Uani d . 1 1 . .
N N2 0.7166(3) 0.2434(2) 0.8493(4) 0.0389(10) Uani d D 1 1 . .
O O1 0.5703(3) 0.4903(2) 0.7240(4) 0.0668(11) Uani d . 1 1 . .
O O2 0.7770(3) 0.17262(19) 1.0857(4) 0.0534(9) Uani d . 1 1 . .
C C1 0.4904(4) 0.3853(3) 0.8237(5) 0.0394(12) Uani d . 1 1 . .
C C2 0.4835(5) 0.4634(3) 0.7754(6) 0.0500(14) Uani d . 1 1 . .
C C3 0.3937(6) 0.5126(3) 0.7840(7) 0.0658(17) Uani d . 1 1 . .
H H3 0.3901 0.5649 0.7519 0.079 Uiso calc R 1 1 . .
C C4 0.3128(5) 0.4821(4) 0.8402(7) 0.0679(17) Uani d . 1 1 . .
H H4 0.2538 0.5145 0.8460 0.082 Uiso calc R 1 1 . .
C C5 0.3145(4) 0.4033(3) 0.8900(6) 0.0481(13) Uani d . 1 1 . .
C C6 0.2266(5) 0.3738(4) 0.9432(7) 0.0690(17) Uani d . 1 1 . .
H H6 0.1677 0.4069 0.9472 0.083 Uiso calc R 1 1 . .
C C7 0.2270(5) 0.2978(4) 0.9885(7) 0.0715(18) Uani d . 1 1 . .
H H7 0.1683 0.2786 1.0223 0.086 Uiso calc R 1 1 . .
C C8 0.3164(5) 0.2483(3) 0.9841(7) 0.0618(15) Uani d . 1 1 . .
H H8 0.3172 0.1963 1.0170 0.074 Uiso calc R 1 1 . .
C C9 0.4018(4) 0.2751(3) 0.9328(6) 0.0490(14) Uani d . 1 1 . .
H H9 0.4596 0.2407 0.9302 0.059 Uiso calc R 1 1 . .
C C10 0.4055(4) 0.3543(3) 0.8829(6) 0.0417(12) Uani d . 1 1 . .
C C11 0.5644(6) 0.5702(3) 0.6675(7) 0.083(2) Uani d . 1 1 . .
H H11A 0.4904 0.5796 0.5845 0.124 Uiso calc R 1 1 . .
H H11B 0.6239 0.5792 0.6215 0.124 Uiso calc R 1 1 . .
H H11C 0.5749 0.6052 0.7589 0.124 Uiso calc R 1 1 . .
C C12 0.5855(4) 0.3402(3) 0.8040(6) 0.0425(12) Uani d . 1 1 . .
H H12 0.6159 0.3564 0.7245 0.051 Uiso calc R 1 1 . .
C C13 0.7872(4) 0.1907(3) 0.9535(5) 0.0364(11) Uani d . 1 1 . .
C C14 0.8782(4) 0.1572(3) 0.8967(6) 0.0338(11) Uani d . 1 1 . .
C C15 0.8636(4) 0.1497(3) 0.7312(6) 0.0372(12) Uani d . 1 1 . .
H H15 0.7964 0.1678 0.6512 0.045 Uiso calc R 1 1 . .
C C16 0.9484(4) 0.1153(3) 0.6847(6) 0.0437(12) Uani d . 1 1 . .
C C17 1.0496(5) 0.0893(3) 0.8001(7) 0.0605(16) Uani d . 1 1 . .
H H17 1.1066 0.0666 0.7671 0.073 Uiso calc R 1 1 . .
C C18 1.0652(5) 0.0975(4) 0.9653(7) 0.0758(19) Uani d . 1 1 . .
H H18 1.1335 0.0806 1.0446 0.091 Uiso calc R 1 1 . .
C C19 0.9793(5) 0.1309(3) 1.0143(6) 0.0548(15) Uani d . 1 1 . .
H H19 0.9898 0.1356 1.1261 0.066 Uiso calc R 1 1 . .
H H2 0.731(4) 0.266(3) 0.764(4) 0.066 Uiso d D 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N1 N2 . . 114.5(4) ?
C13 N2 N1 . . 120.2(4) ?
C13 N2 H2 . . 124(3) ?
N1 N2 H2 . . 114(3) ?
C2 O1 C11 . . 118.1(5) ?
C2 C1 C10 . . 119.3(5) ?
C2 C1 C12 . . 116.0(5) ?
C10 C1 C12 . . 124.7(4) ?
O1 C2 C1 . . 116.3(5) ?
O1 C2 C3 . . 122.3(5) ?
C1 C2 C3 . . 121.4(5) ?
C4 C3 C2 . . 118.7(6) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 122.7(5) ?
C3 C4 H4 . . 118.7 ?
C5 C4 H4 . . 118.7 ?
C4 C5 C6 . . 120.4(6) ?
C4 C5 C10 . . 118.5(5) ?
C6 C5 C10 . . 121.1(5) ?
C7 C6 C5 . . 120.5(6) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.6(6) ?
C6 C7 H7 . . 120.2 ?
C8 C7 H7 . . 120.2 ?
C9 C8 C7 . . 121.0(6) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 121.8(5) ?
C8 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
C1 C10 C5 . . 119.5(5) ?
C1 C10 C9 . . 124.6(4) ?
C5 C10 C9 . . 115.9(5) ?
O1 C11 H11A . . 109.5 ?
O1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N1 C12 C1 . . 123.4(4) ?
N1 C12 H12 . . 118.3 ?
C1 C12 H12 . . 118.3 ?
O2 C13 N2 . . 122.2(4) ?
O2 C13 C14 . . 122.6(4) ?
N2 C13 C14 . . 115.1(4) ?
C15 C14 C19 . . 119.4(4) ?
C15 C14 C13 . . 122.1(4) ?
C19 C14 C13 . . 118.5(4) ?
C16 C15 C14 . . 119.9(4) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 121.4(4) ?
C15 C16 Br1 . . 117.8(4) ?
C17 C16 Br1 . . 120.8(4) ?
C18 C17 C16 . . 118.9(5) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C17 C18 C19 . . 120.4(5) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C14 C19 C18 . . 120.0(5) ?
C14 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
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 C16 . 1.899(5) ?
N1 C12 . 1.282(5) ?
N1 N2 . 1.392(5) ?
N2 C13 . 1.354(6) ?
N2 H2 . 0.898(10) ?
O1 C2 . 1.372(6) ?
O1 C11 . 1.439(6) ?
O2 C13 . 1.228(5) ?
C1 C2 . 1.389(7) ?
C1 C10 . 1.417(6) ?
C1 C12 . 1.462(6) ?
C2 C3 . 1.413(7) ?
C3 C4 . 1.355(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.408(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.410(7) ?
C5 C10 . 1.418(6) ?
C6 C7 . 1.351(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.401(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.356(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.423(6) ?
C9 H9 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.487(6) ?
C14 C15 . 1.380(6) ?
C14 C19 . 1.384(6) ?
C15 C16 . 1.375(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.377(7) ?
C17 C18 . 1.376(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.393(7) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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 4_565 0.898(10) 2.095(13) 2.989(5) 174(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4495761
