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#$Date: 2023-05-09 10:52:57 +0300 (Tue, 09 May 2023) $
#$Revision: 283613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107140.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_8107140
loop_
_publ_author_name
'Amr, Abd El-Galil E.'
'Hafez, Naglaa A. Abdel'
'Ali, Korany A.'
'Al-Omar, Mohamed A.'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of 1,4-dihydro-1-phenylchromeno[4,3-c]pyrazole,
 C16H12N2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1185
_journal_page_last               1187
_journal_paper_doi               10.1515/ncrs-2016-0126
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4475(3)
_cell_length_b                   12.2779(7)
_cell_length_c                   18.0975(11)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.07
_cell_measurement_theta_min      2.25
_cell_volume                     1210.43(12)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3950
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0326
_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)+(0.0347P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2157
_reflns_number_total             2260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0126_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8107140
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1236(2) 0.66660(10) 0.22793(6) 0.0258(3) Uani 1 1 d . . .
N1 N 0.3387(3) 0.65549(11) 0.43710(6) 0.0210(3) Uani 1 1 d . . .
N2 N 0.3913(2) 0.58583(10) 0.37993(6) 0.0176(3) Uani 1 1 d . . .
C1 C 0.2639(3) 0.61371(12) 0.31801(7) 0.0173(3) Uani 1 1 d . . .
C2 C 0.2580(3) 0.56619(12) 0.24389(7) 0.0162(3) Uani 1 1 d . . .
C3 C 0.4335(3) 0.49859(12) 0.21190(7) 0.0185(3) Uani 1 1 d . . .
H3A H 0.5774 0.4801 0.2388 0.022 Uiso 1 1 calc R . .
C4 C 0.4000(3) 0.45791(13) 0.14086(8) 0.0218(3) Uani 1 1 d . . .
H4A H 0.5214 0.4124 0.1193 0.026 Uiso 1 1 calc R . .
C5 C 0.1893(3) 0.48381(13) 0.10147(8) 0.0222(3) Uani 1 1 d . . .
H5A H 0.1638 0.4535 0.0538 0.027 Uiso 1 1 calc R . .
C6 C 0.0162(3) 0.55360(13) 0.13139(8) 0.0214(3) Uani 1 1 d . . .
H6A H -0.1271 0.5717 0.1041 0.026 Uiso 1 1 calc R . .
C7 C 0.0524(3) 0.59720(12) 0.20157(8) 0.0192(3) Uani 1 1 d . . .
C8 C -0.0390(4) 0.75092(13) 0.27784(8) 0.0290(4) Uani 1 1 d . . .
H8A H -0.1816 0.7864 0.3017 0.035 Uiso 1 1 calc R . .
H8B H 0.0522 0.8070 0.2498 0.035 Uiso 1 1 calc R . .
C9 C 0.1240(3) 0.70257(13) 0.33546(8) 0.0214(3) Uani 1 1 d . . .
C10 C 0.1768(3) 0.72543(13) 0.40969(8) 0.0231(3) Uani 1 1 d . . .
H10A H 0.1057 0.7836 0.4369 0.028 Uiso 1 1 calc R . .
C11 C 0.5344(3) 0.49149(12) 0.39610(7) 0.0165(3) Uani 1 1 d . . .
C12 C 0.7481(3) 0.50285(14) 0.43732(7) 0.0202(3) Uani 1 1 d . . .
H12A H 0.8026 0.5729 0.4524 0.024 Uiso 1 1 calc R . .
C13 C 0.8805(3) 0.41070(14) 0.45618(8) 0.0238(3) Uani 1 1 d . . .
H13A H 1.0258 0.4177 0.4848 0.029 Uiso 1 1 calc R . .
C14 C 0.8035(3) 0.30846(13) 0.43377(8) 0.0231(3) Uani 1 1 d . . .
H14A H 0.8957 0.2457 0.4470 0.028 Uiso 1 1 calc R . .
C15 C 0.5907(3) 0.29785(13) 0.39178(7) 0.0206(3) Uani 1 1 d . . .
H15A H 0.5392 0.2279 0.3755 0.025 Uiso 1 1 calc R . .
C16 C 0.4536(3) 0.38923(12) 0.37370(7) 0.0179(3) Uani 1 1 d . . .
H16A H 0.3059 0.3820 0.3462 0.021 Uiso 1 1 calc R . .
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
C7 O1 C8 116.05(13) . .
C10 N1 N2 105.08(11) . .
C1 N2 N1 110.93(12) . .
C1 N2 C11 130.64(12) . .
N1 N2 C11 117.74(11) . .
N2 C1 C9 107.13(12) . .
N2 C1 C2 131.71(14) . .
C9 C1 C2 121.16(13) . .
C3 C2 C7 118.75(12) . .
C3 C2 C1 127.15(14) . .
C7 C2 C1 114.07(13) . .
C2 C3 C4 120.54(14) . .
C2 C3 H3A 119.7 . .
C4 C3 H3A 119.7 . .
C5 C4 C3 120.06(15) . .
C5 C4 H4A 120.0 . .
C3 C4 H4A 120.0 . .
C6 C5 C4 120.28(13) . .
C6 C5 H5A 119.9 . .
C4 C5 H5A 119.9 . .
C5 C6 C7 119.87(15) . .
C5 C6 H6A 120.1 . .
C7 C6 H6A 120.1 . .
O1 C7 C6 117.26(14) . .
O1 C7 C2 122.39(12) . .
C6 C7 C2 120.30(14) . .
O1 C8 C9 109.91(13) . .
O1 C8 H8A 109.7 . .
C9 C8 H8A 109.7 . .
O1 C8 H8B 109.7 . .
C9 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C1 C9 C10 105.45(14) . .
C1 C9 C8 119.18(13) . .
C10 C9 C8 135.37(15) . .
N1 C10 C9 111.40(14) . .
N1 C10 H10A 124.3 . .
C9 C10 H10A 124.3 . .
C12 C11 C16 120.80(14) . .
C12 C11 N2 119.09(13) . .
C16 C11 N2 120.03(13) . .
C13 C12 C11 119.13(15) . .
C13 C12 H12A 120.4 . .
C11 C12 H12A 120.4 . .
C12 C13 C14 120.72(14) . .
C12 C13 H13A 119.6 . .
C14 C13 H13A 119.6 . .
C13 C14 C15 119.81(15) . .
C13 C14 H14A 120.1 . .
C15 C14 H14A 120.1 . .
C16 C15 C14 120.09(15) . .
C16 C15 H15A 120.0 . .
C14 C15 H15A 120.0 . .
C15 C16 C11 119.43(14) . .
C15 C16 H16A 120.3 . .
C11 C16 H16A 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3686(19) .
O1 C8 1.4492(19) .
N1 C10 1.327(2) .
N1 N2 1.3726(17) .
N2 C1 1.3618(18) .
N2 C11 1.4264(19) .
C1 C9 1.368(2) .
C1 C2 1.4632(19) .
C2 C3 1.392(2) .
C2 C7 1.409(2) .
C3 C4 1.391(2) .
C3 H3A 0.9500 .
C4 C5 1.388(2) .
C4 H4A 0.9500 .
C5 C6 1.385(2) .
C5 H5A 0.9500 .
C6 C7 1.392(2) .
C6 H6A 0.9500 .
C8 C9 1.493(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.402(2) .
C10 H10A 0.9500 .
C11 C12 1.390(2) .
C11 C16 1.391(2) .
C12 C13 1.385(2) .
C12 H12A 0.9500 .
C13 C14 1.384(2) .
C13 H13A 0.9500 .
C14 C15 1.393(2) .
C14 H14A 0.9500 .
C15 C16 1.387(2) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
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
C10 N1 N2 C1 0.51(17) . . . .
C10 N1 N2 C11 -171.00(14) . . . .
N1 N2 C1 C9 -0.59(17) . . . .
C11 N2 C1 C9 169.49(15) . . . .
N1 N2 C1 C2 179.52(15) . . . .
C11 N2 C1 C2 -10.4(3) . . . .
N2 C1 C2 C3 -19.9(3) . . . .
C9 C1 C2 C3 160.20(15) . . . .
N2 C1 C2 C7 162.12(15) . . . .
C9 C1 C2 C7 -17.7(2) . . . .
C7 C2 C3 C4 -3.3(2) . . . .
C1 C2 C3 C4 178.82(14) . . . .
C2 C3 C4 C5 -0.6(2) . . . .
C3 C4 C5 C6 2.6(2) . . . .
C4 C5 C6 C7 -0.6(2) . . . .
C8 O1 C7 C6 -149.37(14) . . . .
C8 O1 C7 C2 33.3(2) . . . .
C5 C6 C7 O1 179.30(14) . . . .
C5 C6 C7 C2 -3.4(2) . . . .
C3 C2 C7 O1 -177.53(13) . . . .
C1 C2 C7 O1 0.6(2) . . . .
C3 C2 C7 C6 5.3(2) . . . .
C1 C2 C7 C6 -176.59(13) . . . .
C7 O1 C8 C9 -47.52(18) . . . .
N2 C1 C9 C10 0.42(17) . . . .
C2 C1 C9 C10 -179.68(14) . . . .
N2 C1 C9 C8 -179.33(15) . . . .
C2 C1 C9 C8 0.6(2) . . . .
O1 C8 C9 C1 31.2(2) . . . .
O1 C8 C9 C10 -148.48(19) . . . .
N2 N1 C10 C9 -0.23(18) . . . .
C1 C9 C10 N1 -0.12(18) . . . .
C8 C9 C10 N1 179.58(18) . . . .
C1 N2 C11 C12 142.58(15) . . . .
N1 N2 C11 C12 -47.89(18) . . . .
C1 N2 C11 C16 -40.4(2) . . . .
N1 N2 C11 C16 129.10(14) . . . .
C16 C11 C12 C13 -0.2(2) . . . .
N2 C11 C12 C13 176.80(12) . . . .
C11 C12 C13 C14 0.7(2) . . . .
C12 C13 C14 C15 0.0(2) . . . .
C13 C14 C15 C16 -1.3(2) . . . .
C14 C15 C16 C11 1.8(2) . . . .
C12 C11 C16 C15 -1.1(2) . . . .
N2 C11 C16 C15 -178.00(12) . . . .
