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#$Date: 2023-01-12 12:39:19 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280308 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106458.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_8106458
loop_
_publ_author_name
'Bülbül, Hakan'
'Köysal, Yavuz'
'Macit, Mustafa'
'Yaman, Rukiye'
'Dege, Necmi'
_publ_section_title
;
 Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol,
 C17H12N2O3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              135
_journal_page_last               136
_journal_paper_doi               10.1515/ncrs-2016-0191
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C17 H12 N2 O3'
_chemical_formula_sum            'C17 H12 N2 O3'
_chemical_formula_weight         292.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.200(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2641(5)
_cell_length_b                   12.3968(6)
_cell_length_c                   16.1786(13)
_cell_measurement_reflns_used    8239
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      1.64
_cell_volume                     1384.02(17)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA [10]'
_computing_data_reduction        'X-RED32 [10]'
_computing_molecular_graphics    'ORTEP-3 for Windows [12]'
_computing_publication_material  'WinGX [13]'
_computing_structure_refinement  'SHELXL-97 [11]'
_computing_structure_solution    'SHELXS97 [11]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'w 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  0.1428
_diffrn_reflns_av_sigmaI/netI    0.1384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8884
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        'not measured'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'STOE X-RED [10]'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0905
_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)+(0.0818P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1928
_reflns_number_gt                1601
_reflns_number_total             3177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0191_suppl.cif
_cod_data_source_block           necmi150
_cod_original_cell_volume        1384.02(16)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8106458
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
C1 C 0.8113(4) 0.3274(2) 0.57499(17) 0.0462(7) Uani 1 1 d . . .
C2 C 0.8423(4) 0.2748(2) 0.65536(18) 0.0509(7) Uani 1 1 d . . .
C3 C 0.8641(5) 0.1639(2) 0.6624(2) 0.0587(8) Uani 1 1 d . . .
H3 H 0.8846 0.1307 0.7161 0.070 Uiso 1 1 calc R . .
C4 C 0.8556(5) 0.1028(2) 0.5910(2) 0.0611(8) Uani 1 1 d . . .
H4 H 0.8695 0.0283 0.5960 0.073 Uiso 1 1 calc R . .
C5 C 0.8261(5) 0.1523(2) 0.51121(19) 0.0533(7) Uani 1 1 d . . .
C6 C 0.8030(4) 0.2627(2) 0.50383(19) 0.0516(7) Uani 1 1 d . . .
H6 H 0.7812 0.2947 0.4496 0.062 Uiso 1 1 calc R . .
C7 C 0.7847(6) 0.4444(2) 0.5587(2) 0.0713(10) Uani 1 1 d . . .
H7 H 0.7929 0.4883 0.6064 0.086 Uiso 1 1 calc R . .
C8 C 0.7328(5) 0.5982(2) 0.4770(2) 0.0560(7) Uani 1 1 d . . .
C9 C 0.6874(4) 0.6331(2) 0.3892(2) 0.0505(7) Uani 1 1 d . . .
C10 C 0.6638(5) 0.5607(3) 0.3195(2) 0.0645(9) Uani 1 1 d . . .
H10 H 0.6797 0.4871 0.3305 0.077 Uiso 1 1 calc R . .
C11 C 0.6181(6) 0.5975(3) 0.2363(2) 0.0784(10) Uani 1 1 d . . .
H11 H 0.6015 0.5489 0.1908 0.094 Uiso 1 1 calc R . .
C12 C 0.5959(6) 0.7083(3) 0.2186(3) 0.0858(12) Uani 1 1 d . . .
H12 H 0.5636 0.7326 0.1615 0.103 Uiso 1 1 calc R . .
C13 C 0.6210(5) 0.7801(3) 0.2842(3) 0.0789(11) Uani 1 1 d . . .
H13 H 0.6085 0.8534 0.2716 0.095 Uiso 1 1 calc R . .
C14 C 0.6659(5) 0.7457(2) 0.3714(2) 0.0595(8) Uani 1 1 d . . .
C15 C 0.6900(5) 0.8186(2) 0.4408(3) 0.0697(9) Uani 1 1 d . . .
H15 H 0.6761 0.8922 0.4294 0.084 Uiso 1 1 calc R . .
C16 C 0.7331(6) 0.7832(2) 0.5236(3) 0.0745(10) Uani 1 1 d . . .
H16 H 0.7481 0.8325 0.5686 0.089 Uiso 1 1 calc R . .
C17 C 0.7554(6) 0.6727(2) 0.5422(2) 0.0715(10) Uani 1 1 d . . .
H17 H 0.7860 0.6495 0.5995 0.086 Uiso 1 1 calc R . .
N1 N 0.8553(4) 0.3349(2) 0.73374(17) 0.0608(7) Uani 1 1 d . . .
N2 N 0.7547(5) 0.48626(19) 0.49209(18) 0.0784(10) Uani 1 1 d . . .
O1 O 0.8209(4) 0.08877(15) 0.44248(14) 0.0751(7) Uani 1 1 d . . .
H1 H 0.8025 0.1262 0.3989 0.113 Uiso 1 1 calc R . .
O2 O 0.8685(4) 0.2842(2) 0.80081(15) 0.0903(9) Uani 1 1 d . . .
O3 O 0.8545(5) 0.4327(2) 0.73294(17) 0.0969(9) Uani 1 1 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
C6 C1 C2 116.8(2) . .
C6 C1 C7 116.8(3) . .
C2 C1 C7 126.5(3) . .
C3 C2 C1 121.1(3) . .
C3 C2 N1 117.6(3) . .
C1 C2 N1 121.2(2) . .
C4 C3 C2 120.5(3) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 119.7(3) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
O1 C5 C6 122.3(3) . .
O1 C5 C4 117.7(2) . .
C6 C5 C4 120.0(3) . .
C5 C6 C1 121.9(3) . .
C5 C6 H6 119.0 . .
C1 C6 H6 119.0 . .
N2 C7 C1 125.8(3) . .
N2 C7 H7 117.1 . .
C1 C7 H7 117.1 . .
C17 C8 N2 123.3(3) . .
C17 C8 C9 119.8(3) . .
N2 C8 C9 116.8(3) . .
C10 C9 C8 122.6(3) . .
C10 C9 C14 119.0(3) . .
C8 C9 C14 118.5(3) . .
C11 C10 C9 120.6(3) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C10 C11 C12 120.5(4) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C11 120.4(3) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C14 121.2(3) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C15 C14 C13 122.3(3) . .
C15 C14 C9 119.3(3) . .
C13 C14 C9 118.4(3) . .
C16 C15 C14 120.9(3) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C15 C16 C17 120.4(3) . .
C15 C16 H16 119.8 . .
C17 C16 H16 119.8 . .
C8 C17 C16 121.0(3) . .
C8 C17 H17 119.5 . .
C16 C17 H17 119.5 . .
O3 N1 O2 121.2(3) . .
O3 N1 C2 120.4(3) . .
O2 N1 C2 118.4(3) . .
C7 N2 C8 125.6(3) . .
C5 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(4) .
C1 C2 1.408(4) .
C1 C7 1.476(4) .
C2 C3 1.385(4) .
C2 N1 1.448(4) .
C3 C4 1.367(4) .
C3 H3 0.9300 .
C4 C5 1.384(4) .
C4 H4 0.9300 .
C5 O1 1.353(3) .
C5 C6 1.380(4) .
C6 H6 0.9300 .
C7 N2 1.154(4) .
C7 H7 0.9300 .
C8 C17 1.372(4) .
C8 N2 1.410(4) .
C8 C9 1.421(4) .
C9 C10 1.410(4) .
C9 C14 1.423(4) .
C10 C11 1.361(5) .
C10 H10 0.9300 .
C11 C12 1.401(5) .
C11 H11 0.9300 .
C12 C13 1.353(5) .
C12 H12 0.9300 .
C13 C14 1.411(5) .
C13 H13 0.9300 .
C14 C15 1.410(5) .
C15 C16 1.350(5) .
C15 H15 0.9300 .
C16 C17 1.401(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
N1 O3 1.212(3) .
N1 O2 1.231(3) .
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 2.11 2.889(3) 158.5 4_565
C7 H7 O3 0.93 2.07 2.708(4) 124.2 .
C10 H10 N2 0.93 2.50 2.816(4) 100.2 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.2(4) . . . .
C7 C1 C2 C3 179.6(3) . . . .
C6 C1 C2 N1 179.4(3) . . . .
C7 C1 C2 N1 -1.3(5) . . . .
C1 C2 C3 C4 -0.1(5) . . . .
N1 C2 C3 C4 -179.2(3) . . . .
C2 C3 C4 C5 0.4(5) . . . .
C3 C4 C5 O1 179.3(3) . . . .
C3 C4 C5 C6 -0.8(5) . . . .
O1 C5 C6 C1 -179.1(3) . . . .
C4 C5 C6 C1 1.0(5) . . . .
C2 C1 C6 C5 -0.7(4) . . . .
C7 C1 C6 C5 179.9(3) . . . .
C6 C1 C7 N2 1.4(6) . . . .
C2 C1 C7 N2 -178.0(4) . . . .
C17 C8 C9 C10 179.5(3) . . . .
N2 C8 C9 C10 0.3(5) . . . .
C17 C8 C9 C14 -0.2(5) . . . .
N2 C8 C9 C14 -179.5(3) . . . .
C8 C9 C10 C11 179.2(3) . . . .
C14 C9 C10 C11 -1.0(5) . . . .
C9 C10 C11 C12 0.7(6) . . . .
C10 C11 C12 C13 0.5(6) . . . .
C11 C12 C13 C14 -1.4(6) . . . .
C12 C13 C14 C15 -179.1(4) . . . .
C12 C13 C14 C9 1.0(5) . . . .
C10 C9 C14 C15 -179.7(3) . . . .
C8 C9 C14 C15 0.0(4) . . . .
C10 C9 C14 C13 0.2(5) . . . .
C8 C9 C14 C13 179.9(3) . . . .
C13 C14 C15 C16 -179.9(3) . . . .
C9 C14 C15 C16 0.0(5) . . . .
C14 C15 C16 C17 0.2(6) . . . .
N2 C8 C17 C16 179.6(3) . . . .
C9 C8 C17 C16 0.4(6) . . . .
C15 C16 C17 C8 -0.4(6) . . . .
C3 C2 N1 O3 173.5(3) . . . .
C1 C2 N1 O3 -5.7(5) . . . .
C3 C2 N1 O2 -6.0(4) . . . .
C1 C2 N1 O2 174.8(3) . . . .
C1 C7 N2 C8 -178.8(3) . . . .
C17 C8 N2 C7 3.7(6) . . . .
C9 C8 N2 C7 -177.1(4) . . . .
