#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228253.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_2228253
loop_
_publ_author_name
'Sheng, Liang-Quan'
'Xu, Hua-Jie'
'Du, Na-Na'
'Jiang, Xue-Yue'
_publ_section_title
;
 Methyl 3-[(E)-(2-hydroxy-1-naphthyl)methylidene]carbazate
;
_journal_coeditor_code           BX2318
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3046
_journal_paper_doi               10.1107/S1600536810044041
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H12 N2 O3'
_chemical_formula_moiety         'C13 H12 N2 O3'
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_weight         244.25
_chemical_name_systematic
;
Methyl 3-[(E)-2-hydroxy-1-naphthyl)methylidene]carbazate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1754(3)
_cell_length_b                   9.2787(5)
_cell_length_c                   23.6766(12)
_cell_measurement_reflns_used    2986
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0489
_cell_measurement_theta_min      3.3811
_cell_volume                     1136.97(11)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6329
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0303
_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)+(0.0239P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0579
_reflns_number_gt                1120
_reflns_number_total             1562
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2318.cif
_cod_data_source_block           I
_cod_database_code               2228253
_cod_database_fobs_code          2228253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.7358(4) 0.2360(2) 0.64442(8) 0.0492(5) Uani d . 1 . .
H H1A 0.8342 0.2851 0.6711 0.059 Uiso calc R 1 . .
C C2 0.7869(4) 0.2539(2) 0.58880(8) 0.0538(5) Uani d . 1 . .
H H2A 0.9175 0.3163 0.5774 0.065 Uiso calc R 1 . .
C C3 0.6428(4) 0.1785(2) 0.54858(8) 0.0529(5) Uani d . 1 . .
H H3 0.6800 0.1901 0.5104 0.064 Uiso calc R 1 . .
C C4 0.4483(4) 0.0881(2) 0.56460(7) 0.0460(5) Uani d . 1 . .
H H4 0.3539 0.0397 0.5371 0.055 Uiso calc R 1 . .
C C5 0.3871(3) 0.06633(18) 0.62220(7) 0.0363(4) Uani d . 1 . .
C C6 0.5348(3) 0.14347(18) 0.66256(7) 0.0402(4) Uani d . 1 . .
C C7 0.4774(4) 0.1259(2) 0.72052(7) 0.0478(5) Uani d . 1 . .
H H7 0.5710 0.1780 0.7471 0.057 Uiso calc R 1 . .
C C8 0.2899(4) 0.0355(2) 0.73821(7) 0.0476(5) Uani d . 1 . .
H H8 0.2564 0.0256 0.7766 0.057 Uiso calc R 1 . .
C C9 0.1459(3) -0.04352(19) 0.69896(7) 0.0406(4) Uani d . 1 . .
C C10 0.1867(3) -0.02866(18) 0.64118(7) 0.0354(4) Uani d . 1 . .
C C11 0.0239(3) -0.10114(18) 0.60072(6) 0.0396(4) Uani d . 1 . .
H H11 0.0471 -0.0813 0.5626 0.047 Uiso calc R 1 . .
C C12 -0.4938(4) -0.33819(19) 0.57803(6) 0.0397(4) Uani d . 1 . .
C C13 -0.7307(4) -0.4828(2) 0.64025(8) 0.0554(5) Uani d . 1 . .
H H13A -0.8917 -0.4395 0.6294 0.083 Uiso calc R 1 . .
H H13B -0.7372 -0.5087 0.6795 0.083 Uiso calc R 1 . .
H H13C -0.7014 -0.5677 0.6179 0.083 Uiso calc R 1 . .
N N1 -0.1522(3) -0.19204(16) 0.61512(6) 0.0410(4) Uani d . 1 . .
N N2 -0.2962(3) -0.24594(17) 0.57083(5) 0.0455(4) Uani d . 1 . .
H H2 -0.2578 -0.2193 0.5371 0.055 Uiso calc R 1 . .
O O1 -0.0360(3) -0.13205(14) 0.72081(5) 0.0553(4) Uani d . 1 . .
H H1 -0.1165 -0.1705 0.6951 0.083 Uiso calc R 1 . .
O O2 -0.6293(2) -0.37715(15) 0.53872(5) 0.0548(4) Uani d . 1 . .
O O3 -0.5234(2) -0.38178(12) 0.63113(4) 0.0462(3) Uani d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 C1 C6 . . 120.88(18) ?
C2 C1 H1A . . 119.6 ?
C6 C1 H1A . . 119.6 ?
C1 C2 C3 . . 119.82(19) ?
C1 C2 H2A . . 120.1 ?
C3 C2 H2A . . 120.1 ?
C4 C3 C2 . . 120.82(17) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 121.39(17) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 117.21(16) ?
C4 C5 C10 . . 123.50(16) ?
C6 C5 C10 . . 119.29(15) ?
C7 C6 C1 . . 121.25(17) ?
C7 C6 C5 . . 118.88(17) ?
C1 C6 C5 . . 119.87(15) ?
C8 C7 C6 . . 121.60(17) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C7 C8 C9 . . 120.18(16) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
O1 C9 C10 . . 122.83(16) ?
O1 C9 C8 . . 115.79(15) ?
C10 C9 C8 . . 121.38(17) ?
C9 C10 C5 . . 118.63(16) ?
C9 C10 C11 . . 121.23(16) ?
C5 C10 C11 . . 120.08(14) ?
N1 C11 C10 . . 122.89(14) ?
N1 C11 H11 . . 118.6 ?
C10 C11 H11 . . 118.6 ?
O2 C12 O3 . . 124.41(18) ?
O2 C12 N2 . . 121.93(15) ?
O3 C12 N2 . . 113.66(15) ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 N1 N2 . . 114.73(13) ?
C12 N2 N1 . . 123.02(13) ?
C12 N2 H2 . . 118.5 ?
N1 N2 H2 . . 118.5 ?
C9 O1 H1 . . 109.5 ?
C12 O3 C13 . . 115.17(14) ?
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
C1 C2 . 1.353(2) ?
C1 C6 . 1.416(2) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.397(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.364(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.414(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.418(2) ?
C5 C10 . 1.433(2) ?
C6 C7 . 1.413(2) ?
C7 C8 . 1.350(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.399(2) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.3523(19) ?
C9 C10 . 1.391(2) ?
C10 C11 . 1.442(2) ?
C11 N1 . 1.288(2) ?
C11 H11 . 0.9300 ?
C12 O2 . 1.2203(19) ?
C12 O3 . 1.3294(19) ?
C12 N2 . 1.344(2) ?
C13 O3 . 1.441(2) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 N2 . 1.3804(18) ?
N2 H2 . 0.8600 ?
O1 H1 . 0.8200 ?
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
O1 H1 N1 . 0.82 1.91 2.6332(18) 146.1
N2 H2 O2 3_546 0.86 2.11 2.9626(18) 169.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(3) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C5 C4 C3 C2 . . . . -0.6(3) ?
C6 C5 C4 C3 . . . . 0.6(3) ?
C10 C5 C4 C3 . . . . -179.27(16) ?
C2 C1 C6 C7 . . . . -178.94(18) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . 179.26(17) ?
C10 C5 C6 C7 . . . . -0.9(2) ?
C4 C5 C6 C1 . . . . -0.8(2) ?
C10 C5 C6 C1 . . . . 179.04(15) ?
C1 C6 C7 C8 . . . . -178.46(16) ?
C5 C6 C7 C8 . . . . 1.5(3) ?
C9 C8 C7 C6 . . . . -0.2(3) ?
C7 C8 C9 O1 . . . . 179.49(16) ?
C7 C8 C9 C10 . . . . -1.6(3) ?
C5 C10 C9 O1 . . . . -179.05(14) ?
C5 C10 C9 C8 . . . . 2.1(2) ?
C11 C10 C9 O1 . . . . 4.0(3) ?
C11 C10 C9 C8 . . . . -174.82(16) ?
C9 C10 C5 C4 . . . . 178.98(18) ?
C9 C10 C5 C6 . . . . -0.9(2) ?
C11 C10 C5 C4 . . . . -4.0(2) ?
C11 C10 C5 C6 . . . . 176.13(15) ?
C9 C10 C11 N1 . . . . -6.0(2) ?
C5 C10 C11 N1 . . . . 177.12(14) ?
N2 N1 C11 C10 . . . . 177.35(15) ?
N1 N2 C12 O2 . . . . 175.09(16) ?
N1 N2 C12 O3 . . . . -5.3(2) ?
C12 N2 N1 C11 . . . . -177.71(15) ?
C13 O3 C12 O2 . . . . 0.6(3) ?
C13 O3 C12 N2 . . . . -178.95(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12974042
2 PubChem 135588910
