#------------------------------------------------------------------------------
#$Date: 2023-02-08 10:38:55 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106712.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_8106712
loop_
_publ_author_name
'Hong, Zhi'
'Zhan, Yan-Li'
'Yu, Dang-Ran'
'Li, Ying'
'Yuan, Wen-Jia'
'Zhang, Hong-Yu'
_publ_section_title
;
 The pseudosymmetric crystal structure of
 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6
;
_publ_section_title_footnote     .
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              893
_journal_page_last               895
_journal_paper_doi               10.1515/ncrs-2017-0047
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-02-12 # Formatted by publCIF

;
_cell_angle_alpha                100.7790(10)
_cell_angle_beta                 102.7380(10)
_cell_angle_gamma                93.0650(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4457(6)
_cell_length_b                   11.0520(7)
_cell_length_c                   14.6746(9)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      1.5
_cell_volume                     1460.68(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      291(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16893
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                4723
_reflns_number_total             6612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0047_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106712
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.24900(15) 0.32046(12) 0.38101(10) 0.0473(3) Uani 1 1 d . . .
N2 N 0.24749(15) 0.81438(12) 0.38340(9) 0.0462(3) Uani 1 1 d . . .
O1 O 0.28085(14) 0.25661(11) 0.44079(9) 0.0604(3) Uani 1 1 d . . .
O2 O 0.12406(14) 0.32387(14) 0.33560(11) 0.0796(4) Uani 1 1 d . . .
O3 O 0.42326(11) 0.57580(9) 0.29709(8) 0.0448(3) Uani 1 1 d . . .
O4 O 0.12219(14) 0.82197(14) 0.34006(10) 0.0736(4) Uani 1 1 d . . .
O5 O 0.27881(14) 0.74394(11) 0.43849(9) 0.0597(3) Uani 1 1 d . . .
O6 O 0.42530(11) 1.08039(9) 0.31461(8) 0.0444(3) Uani 1 1 d . . .
C1 C 0.26524(15) 0.40583(13) 0.18647(10) 0.0370(3) Uani 1 1 d . . .
C2 C 0.13272(17) 0.42842(16) 0.12885(13) 0.0517(4) Uani 1 1 d . . .
H2A H 0.0742 0.4835 0.1549 0.062 Uiso 1 1 calc R . .
C3 C 0.08978(19) 0.37035(17) 0.03552(14) 0.0611(5) Uani 1 1 d . . .
H3A H 0.0014 0.3856 -0.0010 0.073 Uiso 1 1 calc R . .
C4 C 0.17596(19) 0.28805(16) -0.00671(11) 0.0519(4) Uani 1 1 d . . .
C5 C 0.1348(3) 0.2270(2) -0.10422(14) 0.0775(7) Uani 1 1 d . . .
H5A H 0.0470 0.2410 -0.1422 0.093 Uiso 1 1 calc R . .
C6 C 0.2215(3) 0.1489(2) -0.14254(14) 0.0892(8) Uani 1 1 d . . .
H6A H 0.1933 0.1105 -0.2067 0.107 Uiso 1 1 calc R . .
C7 C 0.3527(3) 0.1257(2) -0.08672(15) 0.0813(7) Uani 1 1 d . . .
H7A H 0.4115 0.0719 -0.1139 0.098 Uiso 1 1 calc R . .
C8 C 0.3958(2) 0.18126(18) 0.00761(13) 0.0634(5) Uani 1 1 d . . .
H8A H 0.4833 0.1643 0.0443 0.076 Uiso 1 1 calc R . .
C9 C 0.30899(17) 0.26403(15) 0.04991(11) 0.0450(4) Uani 1 1 d . . .
C10 C 0.34958(16) 0.32444(14) 0.14722(10) 0.0411(3) Uani 1 1 d . . .
H10A H 0.4361 0.3082 0.1854 0.049 Uiso 1 1 calc R . .
C11 C 0.31119(15) 0.47606(13) 0.28858(10) 0.0381(3) Uani 1 1 d . . .
H11A H 0.2260 0.5141 0.3045 0.046 Uiso 1 1 calc R . .
C12 C 0.36282(16) 0.39791(13) 0.36058(10) 0.0368(3) Uani 1 1 d . . .
C13 C 0.50148(16) 0.39386(13) 0.40246(10) 0.0385(3) Uani 1 1 d . . .
H13A H 0.5269 0.3425 0.4457 0.046 Uiso 1 1 calc R . .
C14 C 0.61299(16) 0.47066(13) 0.37989(10) 0.0367(3) Uani 1 1 d . . .
C15 C 0.76196(17) 0.46305(15) 0.41221(11) 0.0466(4) Uani 1 1 d . . .
H15A H 0.7937 0.4059 0.4495 0.056 Uiso 1 1 calc R . .
C16 C 0.86248(18) 0.54007(16) 0.38910(12) 0.0547(4) Uani 1 1 d . . .
H16A H 0.9618 0.5351 0.4109 0.066 Uiso 1 1 calc R . .
C17 C 0.81502(19) 0.62473(16) 0.33333(13) 0.0544(4) Uani 1 1 d . . .
H17A H 0.8831 0.6764 0.3179 0.065 Uiso 1 1 calc R . .
C18 C 0.66815(18) 0.63365(14) 0.30024(11) 0.0467(4) Uani 1 1 d . . .
H18A H 0.6373 0.6902 0.2622 0.056 Uiso 1 1 calc R . .
C19 C 0.56747(16) 0.55759(12) 0.32433(10) 0.0367(3) Uani 1 1 d . . .
C20 C 0.27822(15) 0.91593(13) 0.19336(10) 0.0359(3) Uani 1 1 d . . .
C21 C 0.20709(17) 0.98466(15) 0.12736(12) 0.0470(4) Uani 1 1 d . . .
H21A H 0.1788 1.0619 0.1495 0.056 Uiso 1 1 calc R . .
C22 C 0.17998(18) 0.93853(17) 0.03189(12) 0.0520(4) Uani 1 1 d . . .
H22A H 0.1339 0.9851 -0.0104 0.062 Uiso 1 1 calc R . .
C23 C 0.22040(17) 0.82141(16) -0.00415(11) 0.0466(4) Uani 1 1 d . . .
C24 C 0.1960(2) 0.7712(2) -0.10332(12) 0.0642(5) Uani 1 1 d . . .
H24A H 0.1519 0.8167 -0.1471 0.077 Uiso 1 1 calc R . .
C25 C 0.2360(2) 0.6580(2) -0.13518(13) 0.0728(6) Uani 1 1 d . . .
H25A H 0.2196 0.6270 -0.2005 0.087 Uiso 1 1 calc R . .
C26 C 0.3019(2) 0.58723(19) -0.07083(14) 0.0674(5) Uani 1 1 d . . .
H26A H 0.3281 0.5094 -0.0935 0.081 Uiso 1 1 calc R . .
C27 C 0.32780(19) 0.63241(16) 0.02557(12) 0.0537(4) Uani 1 1 d . . .
H27A H 0.3716 0.5849 0.0679 0.064 Uiso 1 1 calc R . .
C28 C 0.28855(16) 0.75060(14) 0.06116(10) 0.0409(3) Uani 1 1 d . . .
C29 C 0.31635(15) 0.80138(13) 0.16038(10) 0.0371(3) Uani 1 1 d . . .
H29A H 0.3614 0.7557 0.2038 0.044 Uiso 1 1 calc R . .
C30 C 0.31370(15) 0.97723(13) 0.29786(10) 0.0377(3) Uani 1 1 d . . .
H30A H 0.2254 1.0113 0.3120 0.045 Uiso 1 1 calc R . .
C31 C 0.36229(16) 0.89311(13) 0.36583(10) 0.0363(3) Uani 1 1 d . . .
C32 C 0.50095(16) 0.88535(13) 0.40550(9) 0.0373(3) Uani 1 1 d . . .
H32A H 0.5260 0.8301 0.4456 0.045 Uiso 1 1 calc R . .
C33 C 0.61304(15) 0.96414(13) 0.38553(9) 0.0356(3) Uani 1 1 d . . .
C34 C 0.76176(16) 0.95318(15) 0.41492(10) 0.0435(4) Uani 1 1 d . . .
H34A H 0.7928 0.8912 0.4475 0.052 Uiso 1 1 calc R . .
C35 C 0.86328(17) 1.03392(16) 0.39596(11) 0.0486(4) Uani 1 1 d . . .
H35A H 0.9624 1.0265 0.4158 0.058 Uiso 1 1 calc R . .
C36 C 0.81691(18) 1.12585(15) 0.34729(11) 0.0490(4) Uani 1 1 d . . .
H36A H 0.8855 1.1802 0.3349 0.059 Uiso 1 1 calc R . .
C37 C 0.67039(17) 1.13794(14) 0.31694(11) 0.0440(4) Uani 1 1 d . . .
H37A H 0.6402 1.1991 0.2834 0.053 Uiso 1 1 calc R . .
C38 C 0.56868(15) 1.05810(12) 0.33689(10) 0.0359(3) 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
O1 N1 O2 123.72(14) . .
O1 N1 C12 119.81(14) . .
O2 N1 C12 116.48(13) . .
O5 N2 O4 123.57(14) . .
O5 N2 C31 119.63(13) . .
O4 N2 C31 116.79(13) . .
C19 O3 C11 119.88(11) . .
C38 O6 C30 118.47(11) . .
C10 C1 C2 118.95(14) . .
C10 C1 C11 122.30(13) . .
C2 C1 C11 118.72(14) . .
C3 C2 C1 120.60(17) . .
C3 C2 H2A 119.7 . .
C1 C2 H2A 119.7 . .
C2 C3 C4 121.40(16) . .
C2 C3 H3A 119.3 . .
C4 C3 H3A 119.3 . .
C3 C4 C9 118.83(15) . .
C3 C4 C5 122.71(19) . .
C9 C4 C5 118.46(19) . .
C6 C5 C4 120.9(2) . .
C6 C5 H5A 119.5 . .
C4 C5 H5A 119.5 . .
C5 C6 C7 120.50(19) . .
C5 C6 H6A 119.7 . .
C7 C6 H6A 119.7 . .
C8 C7 C6 120.5(2) . .
C8 C7 H7A 119.7 . .
C6 C7 H7A 119.7 . .
C7 C8 C9 120.6(2) . .
C7 C8 H8A 119.7 . .
C9 C8 H8A 119.7 . .
C8 C9 C4 118.94(16) . .
C8 C9 C10 122.64(16) . .
C4 C9 C10 118.42(15) . .
C1 C10 C9 121.78(14) . .
C1 C10 H10A 119.1 . .
C9 C10 H10A 119.1 . .
O3 C11 C12 109.82(11) . .
O3 C11 C1 109.80(11) . .
C12 C11 C1 114.77(12) . .
O3 C11 H11A 107.4 . .
C12 C11 H11A 107.4 . .
C1 C11 H11A 107.4 . .
C13 C12 N1 120.13(13) . .
C13 C12 C11 124.39(13) . .
N1 C12 C11 115.45(13) . .
C12 C13 C14 119.06(13) . .
C12 C13 H13A 120.5 . .
C14 C13 H13A 120.5 . .
C15 C14 C19 119.04(14) . .
C15 C14 C13 123.17(14) . .
C19 C14 C13 117.78(13) . .
C16 C15 C14 120.23(15) . .
C16 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
C15 C16 C17 119.78(16) . .
C15 C16 H16A 120.1 . .
C17 C16 H16A 120.1 . .
C18 C17 C16 121.04(15) . .
C18 C17 H17A 119.5 . .
C16 C17 H17A 119.5 . .
C17 C18 C19 119.20(15) . .
C17 C18 H18A 120.4 . .
C19 C18 H18A 120.4 . .
O3 C19 C18 117.71(13) . .
O3 C19 C14 121.46(12) . .
C18 C19 C14 120.70(14) . .
C29 C20 C21 119.42(14) . .
C29 C20 C30 123.25(13) . .
C21 C20 C30 117.27(13) . .
C22 C21 C20 120.49(15) . .
C22 C21 H21A 119.8 . .
C20 C21 H21A 119.8 . .
C21 C22 C23 121.25(15) . .
C21 C22 H22A 119.4 . .
C23 C22 H22A 119.4 . .
C22 C23 C28 118.77(14) . .
C22 C23 C24 122.81(16) . .
C28 C23 C24 118.41(17) . .
C25 C24 C23 121.05(18) . .
C25 C24 H24A 119.5 . .
C23 C24 H24A 119.5 . .
C24 C25 C26 120.66(17) . .
C24 C25 H25A 119.7 . .
C26 C25 H25A 119.7 . .
C27 C26 C25 120.19(19) . .
C27 C26 H26A 119.9 . .
C25 C26 H26A 119.9 . .
C26 C27 C28 120.57(18) . .
C26 C27 H27A 119.7 . .
C28 C27 H27A 119.7 . .
C27 C28 C23 119.11(14) . .
C27 C28 C29 122.13(14) . .
C23 C28 C29 118.76(14) . .
C20 C29 C28 121.27(14) . .
C20 C29 H29A 119.4 . .
C28 C29 H29A 119.4 . .
O6 C30 C31 109.55(11) . .
O6 C30 C20 108.85(11) . .
C31 C30 C20 115.14(12) . .
O6 C30 H30A 107.7 . .
C31 C30 H30A 107.7 . .
C20 C30 H30A 107.7 . .
C32 C31 N2 120.50(13) . .
C32 C31 C30 123.48(13) . .
N2 C31 C30 115.97(13) . .
C31 C32 C33 119.13(13) . .
C31 C32 H32A 120.4 . .
C33 C32 H32A 120.4 . .
C34 C33 C38 118.88(13) . .
C34 C33 C32 123.33(13) . .
C38 C33 C32 117.75(13) . .
C35 C34 C33 120.37(15) . .
C35 C34 H34A 119.8 . .
C33 C34 H34A 119.8 . .
C34 C35 C36 119.77(15) . .
C34 C35 H35A 120.1 . .
C36 C35 H35A 120.1 . .
C37 C36 C35 120.89(14) . .
C37 C36 H36A 119.6 . .
C35 C36 H36A 119.6 . .
C36 C37 C38 119.39(15) . .
C36 C37 H37A 120.3 . .
C38 C37 H37A 120.3 . .
O6 C38 C37 117.93(13) . .
O6 C38 C33 121.17(12) . .
C37 C38 C33 120.68(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O1 1.2230(16) .
N1 O2 1.2271(18) .
N1 C12 1.4554(18) .
N2 O5 1.2255(16) .
N2 O4 1.2292(17) .
N2 C31 1.4511(18) .
O3 C19 1.3694(17) .
O3 C11 1.4548(16) .
O6 C38 1.3684(17) .
O6 C30 1.4574(16) .
C1 C10 1.364(2) .
C1 C2 1.411(2) .
C1 C11 1.509(2) .
C2 C3 1.360(2) .
C2 H2A 0.9300 .
C3 C4 1.402(3) .
C3 H3A 0.9300 .
C4 C9 1.413(2) .
C4 C5 1.421(2) .
C5 C6 1.353(3) .
C5 H5A 0.9300 .
C6 C7 1.392(3) .
C6 H6A 0.9300 .
C7 C8 1.366(3) .
C7 H7A 0.9300 .
C8 C9 1.410(2) .
C8 H8A 0.9300 .
C9 C10 1.417(2) .
C10 H10A 0.9300 .
C11 C12 1.5031(19) .
C11 H11A 0.9800 .
C12 C13 1.325(2) .
C13 C14 1.4502(19) .
C13 H13A 0.9300 .
C14 C15 1.395(2) .
C14 C19 1.3982(19) .
C15 C16 1.380(2) .
C15 H15A 0.9300 .
C16 C17 1.384(2) .
C16 H16A 0.9300 .
C17 C18 1.380(2) .
C17 H17A 0.9300 .
C18 C19 1.382(2) .
C18 H18A 0.9300 .
C20 C29 1.3650(19) .
C20 C21 1.417(2) .
C20 C30 1.511(2) .
C21 C22 1.360(2) .
C21 H21A 0.9300 .
C22 C23 1.410(2) .
C22 H22A 0.9300 .
C23 C28 1.417(2) .
C23 C24 1.420(2) .
C24 C25 1.355(3) .
C24 H24A 0.9300 .
C25 C26 1.400(3) .
C25 H25A 0.9300 .
C26 C27 1.371(2) .
C26 H26A 0.9300 .
C27 C28 1.414(2) .
C27 H27A 0.9300 .
C28 C29 1.419(2) .
C29 H29A 0.9300 .
C30 C31 1.504(2) .
C30 H30A 0.9800 .
C31 C32 1.325(2) .
C32 C33 1.4487(19) .
C32 H32A 0.9300 .
C33 C34 1.394(2) .
C33 C38 1.3983(19) .
C34 C35 1.383(2) .
C34 H34A 0.9300 .
C35 C36 1.384(2) .
C35 H35A 0.9300 .
C36 C37 1.379(2) .
C36 H36A 0.9300 .
C37 C38 1.385(2) .
C37 H37A 0.9300 .
