#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102368.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_8102368
loop_
_publ_author_name
'Congshan Zhou'
'Haiyun Hou'
'Tao Yang'
_publ_section_title
;
 Crystal structure of
 2-nitro-N'-(2-methoxynaphthylidene)benzohydrazide, C19H15N3O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              37
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C19 H15 N3 O4'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.34
_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                 105.360(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.909(4)
_cell_length_b                   11.084(4)
_cell_length_c                   14.888(6)
_cell_measurement_reflns_used    1738
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1735.9(11)
_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 [10]'
_computing_structure_solution    'SHELXS-97 [9]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14186
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0496
_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/[σ²(Fo²)+(0.0532P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                2288
_reflns_number_total             3765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2452.cff
_cod_data_source_block           1
_cod_original_cell_volume        1735.9(12)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8102368
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.06000(12) 0.39633(11) 1.09887(9) 0.0558(4) Uani 1 1 d . . .
O2 O 0.54148(14) 0.51998(14) 0.75646(10) 0.0719(5) Uani 1 1 d . . .
O3 O 0.95884(14) 0.18853(13) 0.95510(10) 0.0703(5) Uani 1 1 d . . .
O4 O 0.84727(19) 0.03014(15) 0.94475(11) 0.0965(6) Uani 1 1 d . . .
N1 N 0.86096(14) 0.41711(13) 1.00934(11) 0.0467(4) Uani 1 1 d D . .
N2 N 0.73784(13) 0.37422(12) 0.98340(10) 0.0438(4) Uani 1 1 d . . .
N3 N 0.89631(16) 0.11880(15) 0.98671(11) 0.0524(4) Uani 1 1 d . . .
C1 C 0.90839(15) 0.25282(16) 1.12012(12) 0.0417(4) Uani 1 1 d . . .
C2 C 0.88155(16) 0.14061(17) 1.08003(12) 0.0435(4) Uani 1 1 d . . .
C3 C 0.8425(2) 0.04571(19) 1.12485(15) 0.0609(6) Uani 1 1 d . . .
H3 H 0.8244 -0.0288 1.0956 0.073 Uiso 1 1 calc R . .
C4 C 0.8306(2) 0.0622(2) 1.21298(16) 0.0750(7) Uani 1 1 d . . .
H4 H 0.8042 -0.0013 1.2442 0.090 Uiso 1 1 calc R . .
C5 C 0.8575(2) 0.1713(2) 1.25508(16) 0.0776(7) Uani 1 1 d . . .
H5 H 0.8494 0.1821 1.3152 0.093 Uiso 1 1 calc R . .
C6 C 0.8965(2) 0.2663(2) 1.20964(14) 0.0635(6) Uani 1 1 d . . .
H6 H 0.9151 0.3403 1.2396 0.076 Uiso 1 1 calc R . .
C7 C 0.95013(17) 0.35987(16) 1.07388(12) 0.0421(4) Uani 1 1 d . . .
C8 C 0.66176(16) 0.43743(16) 0.92215(12) 0.0423(4) Uani 1 1 d . . .
H8 H 0.6950 0.5032 0.8977 0.051 Uiso 1 1 calc R . .
C9 C 0.52649(16) 0.41418(14) 0.88767(12) 0.0407(4) Uani 1 1 d . . .
C10 C 0.46529(18) 0.46444(17) 0.80282(14) 0.0522(5) Uani 1 1 d . . .
C11 C 0.3340(2) 0.4560(2) 0.76600(16) 0.0667(6) Uani 1 1 d . . .
H11 H 0.2951 0.4904 0.7085 0.080 Uiso 1 1 calc R . .
C12 C 0.2639(2) 0.3974(2) 0.81447(17) 0.0687(6) Uani 1 1 d . . .
H12 H 0.1764 0.3923 0.7895 0.082 Uiso 1 1 calc R . .
C13 C 0.31850(18) 0.34412(17) 0.90119(15) 0.0528(5) Uani 1 1 d . . .
C14 C 0.2436(2) 0.28608(19) 0.95170(18) 0.0680(6) Uani 1 1 d . . .
H14 H 0.1561 0.2816 0.9267 0.082 Uiso 1 1 calc R . .
C15 C 0.2959(2) 0.23712(19) 1.0352(2) 0.0736(7) Uani 1 1 d . . .
H15 H 0.2448 0.1995 1.0679 0.088 Uiso 1 1 calc R . .
C16 C 0.4268(2) 0.24262(18) 1.07304(16) 0.0662(6) Uani 1 1 d . . .
H16 H 0.4627 0.2079 1.1309 0.079 Uiso 1 1 calc R . .
C17 C 0.50307(19) 0.29789(16) 1.02671(14) 0.0521(5) Uani 1 1 d . . .
H17 H 0.5903 0.3004 1.0535 0.063 Uiso 1 1 calc R . .
C18 C 0.45223(16) 0.35145(15) 0.93882(13) 0.0423(4) Uani 1 1 d . . .
C19 C 0.4868(3) 0.5922(2) 0.67731(19) 0.1061(10) Uani 1 1 d . . .
H19A H 0.4396 0.5419 0.6277 0.159 Uiso 1 1 calc R . .
H19B H 0.5530 0.6330 0.6577 0.159 Uiso 1 1 calc R . .
H19C H 0.4309 0.6506 0.6930 0.159 Uiso 1 1 calc R . .
H1 H 0.881(2) 0.4815(13) 0.9790(13) 0.080 Uiso 1 1 d D . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C19 119.86(18) . . ?
C7 N1 N2 120.54(15) . . ?
C7 N1 H1 120.8(14) . . ?
N2 N1 H1 118.5(14) . . ?
C8 N2 N1 114.44(15) . . ?
O3 N3 O4 122.50(18) . . ?
O3 N3 C2 118.78(16) . . ?
O4 N3 C2 118.71(17) . . ?
C2 C1 C6 116.91(17) . . ?
C2 C1 C7 124.78(16) . . ?
C6 C1 C7 118.31(17) . . ?
C3 C2 C1 122.63(18) . . ?
C3 C2 N3 117.53(18) . . ?
C1 C2 N3 119.83(16) . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N1 122.01(17) . . ?
O1 C7 C1 120.82(17) . . ?
N1 C7 C1 117.03(16) . . ?
N2 C8 C9 124.50(16) . . ?
N2 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C10 C9 C18 118.59(16) . . ?
C10 C9 C8 116.87(16) . . ?
C18 C9 C8 124.34(16) . . ?
O2 C10 C9 115.77(17) . . ?
O2 C10 C11 122.21(19) . . ?
C9 C10 C11 122.00(19) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 C18 118.73(18) . . ?
C14 C13 C18 119.8(2) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 121.18(19) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 116.91(17) . . ?
C17 C18 C9 124.03(16) . . ?
C13 C18 C9 119.03(17) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.226(2) . ?
O2 C10 1.360(2) . ?
O2 C19 1.419(3) . ?
O3 N3 1.2059(19) . ?
O4 N3 1.2104(19) . ?
N1 C7 1.333(2) . ?
N1 N2 1.3799(19) . ?
N1 H1 0.901(9) . ?
N2 C8 1.269(2) . ?
N3 C2 1.460(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.381(3) . ?
C1 C7 1.502(2) . ?
C2 C3 1.373(3) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.451(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(2) . ?
C9 C18 1.431(2) . ?
C10 C11 1.395(3) . ?
C11 C12 1.348(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(3) . ?
C13 C18 1.420(2) . ?
C14 C15 1.338(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.410(3) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
N1 H1 O1 0.901(9) 1.998(10) 2.890(2) 170(2) 3_767
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7839004
