#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/18/8101803.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_8101803
loop_
_publ_author_name
'Wen, P.-H.'
_publ_section_title
;
Crystal structure of naphthalen-1-yl-(4-nitro-benzylidene)amine, 
C₁₇H₁₂N₂O₂
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              397
_journal_page_last               398
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C17 H12 N2 O2'
_chemical_formula_weight         276.29
_chemical_name_systematic
;
 naphthalen-1-yl-(4-nitro-benzylidene)-amine
;
_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                   7.2528(8)
_cell_length_b                   12.3005(10)
_cell_length_c                   15.2083(12)
_cell_measurement_reflns_used    743
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.09
_cell_measurement_theta_min      2.68
_cell_volume                     1356.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       omega
_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  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6115
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0457
_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)+(0.0000P)²+0.0198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1604
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1562.cff
_cod_data_source_block           xb0364m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               8101803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1199(3) 0.49212(19) 0.67029(15) 0.0487(6) Uani 1 4 a d . . .
C2 C 0.0665(3) 0.3861(2) 0.68538(16) 0.0530(7) Uani 1 4 a d . . .
H2 H 0.0277 0.3641 0.7409 0.064 Uiso 1 4 a calc R . .
C3 C 0.0718(3) 0.31347(19) 0.61669(15) 0.0490(6) Uani 1 4 a d . . .
H3 H 0.0367 0.2416 0.6257 0.059 Uiso 1 4 a calc R . .
C4 C 0.1291(4) 0.34709(18) 0.53414(14) 0.0446(6) Uani 1 4 a d . . .
C5 C 0.1790(4) 0.45469(19) 0.52116(15) 0.0559(7) Uani 1 4 a d . . .
H5 H 0.2154 0.4778 0.4656 0.067 Uiso 1 4 a calc R . .
C6 C 0.1753(4) 0.52780(19) 0.58985(16) 0.0561(7) Uani 1 4 a d . . .
H6 H 0.2098 0.5998 0.5814 0.067 Uiso 1 4 a calc R . .
C7 C 0.1417(4) 0.27053(19) 0.46026(14) 0.0506(6) Uani 1 4 a d . . .
H7 H 0.1853 0.2953 0.4064 0.061 Uiso 1 4 a calc R . .
C8 C 0.1053(3) 0.10271(19) 0.39316(15) 0.0469(6) Uani 1 4 a d . . .
C9 C 0.0666(4) 0.1366(2) 0.30990(17) 0.0569(7) Uani 1 4 a d . . .
H9 H 0.0339 0.2088 0.3002 0.068 Uiso 1 4 a calc R . .
C10 C 0.0754(4) 0.0641(2) 0.23833(16) 0.0653(8) Uani 1 4 a d . . .
H10 H 0.0463 0.0881 0.1820 0.078 Uiso 1 4 a calc R . .
C11 C 0.1262(4) -0.0402(2) 0.25152(17) 0.0627(7) Uani 1 4 a d . . .
H11 H 0.1363 -0.0866 0.2035 0.075 Uiso 1 4 a calc R . .
C12 C 0.1641(4) -0.08035(19) 0.33606(16) 0.0533(7) Uani 1 4 a d . . .
C13 C 0.2163(4) -0.1886(2) 0.35148(19) 0.0683(8) Uani 1 4 a d . . .
H13 H 0.2283 -0.2359 0.3041 0.082 Uiso 1 4 a calc R . .
C14 C 0.2495(5) -0.2256(2) 0.4334(2) 0.0787(10) Uani 1 4 a d . . .
H14 H 0.2843 -0.2976 0.4418 0.094 Uiso 1 4 a calc R . .
C15 C 0.2318(5) -0.1556(2) 0.5061(2) 0.0764(9) Uani 1 4 a d . . .
H15 H 0.2520 -0.1819 0.5626 0.092 Uiso 1 4 a calc R . .
C16 C 0.1853(4) -0.0500(2) 0.49401(16) 0.0605(7) Uani 1 4 a d . . .
H16 H 0.1757 -0.0040 0.5423 0.073 Uiso 1 4 a calc R . .
C17 C 0.1513(3) -0.00879(18) 0.40870(15) 0.0475(6) Uani 1 4 a d . . .
N1 N 0.1226(3) 0.5685(2) 0.74491(16) 0.0668(7) Uani 1 4 a d . . .
N2 N 0.0947(3) 0.17178(16) 0.46776(12) 0.0508(6) Uani 1 4 a d . . .
O1 O 0.1633(4) 0.66313(17) 0.72992(14) 0.0925(7) Uani 1 4 a d . . .
O2 O 0.0873(4) 0.5339(2) 0.81795(14) 0.0977(8) Uani 1 4 a 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
C6 C1 C2 122.5(2) . . ?
C6 C1 N1 118.9(2) . . ?
C2 C1 N1 118.6(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 C7 121.4(2) . . ?
C5 C4 C7 119.1(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C4 122.0(2) . . ?
N2 C7 H7 119.0 . . ?
C4 C7 H7 119.0 . . ?
C9 C8 N2 123.3(2) . . ?
C9 C8 C17 119.7(2) . . ?
N2 C8 C17 117.0(2) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.6(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 122.6(2) . . ?
C13 C12 C17 118.5(2) . . ?
C11 C12 C17 118.9(2) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 118.8(2) . . ?
C16 C17 C8 122.4(2) . . ?
C12 C17 C8 118.8(2) . . ?
O2 N1 O1 123.6(2) . . ?
O2 N1 C1 118.6(3) . . ?
O1 N1 C1 117.8(3) . . ?
C7 N2 C8 119.2(2) . . ?
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
C1 C6 1.360(3) . ?
C1 C2 1.380(3) . ?
C1 N1 1.473(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C7 1.469(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.267(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(3) . ?
C8 N2 1.419(3) . ?
C8 C17 1.431(3) . ?
C9 C10 1.409(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.349(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(4) . ?
C12 C17 1.416(3) . ?
C13 C14 1.347(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.415(3) . ?
C16 H16 0.9300 . ?
N1 O2 1.216(3) . ?
N1 O1 1.223(3) . ?
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 C3 -177.1(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C7 178.1(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C7 C4 C5 C6 -177.7(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
N1 C1 C6 C5 177.5(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C3 C4 C7 N2 2.5(4) . . . . ?
C5 C4 C7 N2 -178.7(3) . . . . ?
N2 C8 C9 C10 -178.6(2) . . . . ?
C17 C8 C9 C10 -1.5(4) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C9 C10 C11 C12 2.6(4) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C10 C11 C12 C17 -1.0(4) . . . . ?
C11 C12 C13 C14 -179.1(3) . . . . ?
C17 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C15 C16 C17 C12 0.9(4) . . . . ?
C15 C16 C17 C8 -178.8(3) . . . . ?
C13 C12 C17 C16 -2.2(4) . . . . ?
C11 C12 C17 C16 178.6(3) . . . . ?
C13 C12 C17 C8 177.5(3) . . . . ?
C11 C12 C17 C8 -1.7(4) . . . . ?
C9 C8 C17 C16 -177.3(2) . . . . ?
N2 C8 C17 C16 0.0(4) . . . . ?
C9 C8 C17 C12 3.0(4) . . . . ?
N2 C8 C17 C12 -179.7(2) . . . . ?
C6 C1 N1 O2 -174.1(3) . . . . ?
C2 C1 N1 O2 3.9(4) . . . . ?
C6 C1 N1 O1 4.8(4) . . . . ?
C2 C1 N1 O1 -177.2(3) . . . . ?
C4 C7 N2 C8 178.2(2) . . . . ?
C9 C8 N2 C7 -36.1(4) . . . . ?
C17 C8 N2 C7 146.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 542008
