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#$Date: 2023-01-25 11:36:45 +0200 (Wed, 25 Jan 2023) $
#$Revision: 280589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106583.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_8106583
loop_
_publ_author_name
'Okasha, Rawda M.'
'Amr, Abd El-Galil E.'
'El-Agrody, Ahmed M.'
'Al-Omar, Mohamed A.'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of
 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              497
_journal_page_last               499
_journal_paper_doi               10.1515/ncrs-2016-0338
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_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_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.747(2)
_cell_angle_beta                 104.384(2)
_cell_angle_gamma                101.768(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5971(3)
_cell_length_b                   9.8586(3)
_cell_length_c                   10.6199(4)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.43
_cell_measurement_theta_min      4.35
_cell_volume                     842.69(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8461
_diffrn_reflns_theta_full        66.72
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.9160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.022(2)
_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    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0482
_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)+(0.0680P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                1905
_reflns_number_total             2941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0338_suppl.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106583
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
O1 O 0.83623(18) 0.40865(14) 0.54328(13) 0.0528(4) Uani 1 1 d . . .
O2 O 0.3608(2) 0.87430(18) 0.12590(15) 0.0774(6) Uani 1 1 d . . .
N1 N 0.9375(3) 0.3536(2) 0.7395(2) 0.0589(6) Uani 1 1 d . . .
N2 N 0.8629(3) 0.6056(2) 0.97655(19) 0.0767(7) Uani 1 1 d . . .
C1 C 0.7481(2) 0.4836(2) 0.45874(18) 0.0439(5) Uani 1 1 d . . .
C2 C 0.7163(3) 0.4301(2) 0.32587(19) 0.0529(6) Uani 1 1 d . . .
H2A H 0.7503 0.3482 0.3004 0.063 Uiso 1 1 calc R . .
C3 C 0.6361(3) 0.4967(2) 0.23322(19) 0.0535(6) Uani 1 1 d . . .
H3A H 0.6170 0.4623 0.1425 0.064 Uiso 1 1 calc R . .
C4 C 0.5809(2) 0.6164(2) 0.27006(18) 0.0451(5) Uani 1 1 d . . .
C5 C 0.4962(3) 0.6851(2) 0.17349(19) 0.0518(6) Uani 1 1 d . . .
H5A H 0.4773 0.6514 0.0827 0.062 Uiso 1 1 calc R . .
C6 C 0.4422(3) 0.7989(2) 0.2102(2) 0.0543(6) Uani 1 1 d . . .
C7 C 0.4666(3) 0.8474(2) 0.3442(2) 0.0540(6) Uani 1 1 d . . .
H7A H 0.4250 0.9250 0.3693 0.065 Uiso 1 1 calc R . .
C8 C 0.5494(3) 0.7842(2) 0.4383(2) 0.0488(5) Uani 1 1 d . . .
H8A H 0.5667 0.8199 0.5285 0.059 Uiso 1 1 calc R . .
C9 C 0.6105(2) 0.6666(2) 0.40522(17) 0.0411(5) Uani 1 1 d . . .
C10 C 0.7004(2) 0.59975(19) 0.50236(17) 0.0399(5) Uani 1 1 d . . .
C11 C 0.7463(2) 0.65795(19) 0.64729(17) 0.0400(5) Uani 1 1 d . . .
H11A H 0.6430 0.6680 0.6705 0.048 Uiso 1 1 calc R . .
C12 C 0.8185(2) 0.5554(2) 0.72769(17) 0.0429(5) Uani 1 1 d . . .
C13 C 0.8640(2) 0.4439(2) 0.67517(18) 0.0441(5) Uani 1 1 d . . .
C14 C 0.8440(3) 0.5814(2) 0.8652(2) 0.0513(6) Uani 1 1 d . . .
C15 C 0.8674(2) 0.80160(19) 0.68330(18) 0.0416(5) Uani 1 1 d . . .
C16 C 0.8578(3) 0.9016(2) 0.7802(2) 0.0562(6) Uani 1 1 d . . .
H16A H 0.7704 0.8831 0.8207 0.067 Uiso 1 1 calc R . .
C17 C 0.9744(4) 1.0285(2) 0.8190(3) 0.0724(8) Uani 1 1 d . . .
H17A H 0.9669 1.0961 0.8861 0.087 Uiso 1 1 calc R . .
C18 C 1.0997(3) 1.0564(3) 0.7613(3) 0.0791(9) Uani 1 1 d . . .
H18A H 1.1796 1.1434 0.7882 0.095 Uiso 1 1 calc R . .
C19 C 1.1104(3) 0.9591(3) 0.6644(3) 0.0756(8) Uani 1 1 d . . .
H19A H 1.1975 0.9792 0.6239 0.091 Uiso 1 1 calc R . .
C20 C 0.9949(3) 0.8315(2) 0.6250(2) 0.0572(6) Uani 1 1 d . . .
H20A H 1.0034 0.7644 0.5578 0.069 Uiso 1 1 calc R . .
C21 C 0.3207(4) 0.8236(3) -0.0114(2) 0.1002(11) Uani 1 1 d . . .
H21A H 0.2560 0.8819 -0.0608 0.150 Uiso 1 1 calc R . .
H21B H 0.2557 0.7263 -0.0299 0.150 Uiso 1 1 calc R . .
H21C H 0.4227 0.8278 -0.0379 0.150 Uiso 1 1 calc R . .
H2N1 H 0.960(4) 0.284(3) 0.692(3) 0.099(10) Uiso 1 1 d . . .
H1N1 H 0.983(3) 0.377(3) 0.836(3) 0.091(9) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 O1 C1 119.00(15) . .
C6 O2 C21 117.2(2) . .
C13 N1 H2N1 117.9(19) . .
C13 N1 H1N1 118.7(16) . .
H2N1 N1 H1N1 122(3) . .
C10 C1 C2 123.45(18) . .
C10 C1 O1 123.12(17) . .
C2 C1 O1 113.43(17) . .
C3 C2 C1 119.19(19) . .
C3 C2 H2A 120.4 . .
C1 C2 H2A 120.4 . .
C2 C3 C4 120.90(19) . .
C2 C3 H3A 119.6 . .
C4 C3 H3A 119.6 . .
C9 C4 C3 118.95(18) . .
C9 C4 C5 120.16(19) . .
C3 C4 C5 120.89(18) . .
C6 C5 C4 120.29(19) . .
C6 C5 H5A 119.9 . .
C4 C5 H5A 119.9 . .
C5 C6 O2 125.4(2) . .
C5 C6 C7 120.09(19) . .
O2 C6 C7 114.5(2) . .
C8 C7 C6 120.5(2) . .
C8 C7 H7A 119.7 . .
C6 C7 H7A 119.7 . .
C7 C8 C9 121.6(2) . .
C7 C8 H8A 119.2 . .
C9 C8 H8A 119.2 . .
C4 C9 C8 117.34(17) . .
C4 C9 C10 120.03(18) . .
C8 C9 C10 122.62(18) . .
C1 C10 C9 117.41(17) . .
C1 C10 C11 121.23(17) . .
C9 C10 C11 121.33(17) . .
C10 C11 C12 109.72(16) . .
C10 C11 C15 112.99(15) . .
C12 C11 C15 109.87(15) . .
C10 C11 H11A 108.0 . .
C12 C11 H11A 108.0 . .
C15 C11 H11A 108.0 . .
C13 C12 C14 118.74(18) . .
C13 C12 C11 123.63(17) . .
C14 C12 C11 117.59(17) . .
N1 C13 C12 127.48(19) . .
N1 C13 O1 110.50(18) . .
C12 C13 O1 122.01(17) . .
N2 C14 C12 178.2(2) . .
C16 C15 C20 118.6(2) . .
C16 C15 C11 120.72(19) . .
C20 C15 C11 120.59(18) . .
C15 C16 C17 120.7(2) . .
C15 C16 H16A 119.7 . .
C17 C16 H16A 119.7 . .
C18 C17 C16 120.2(2) . .
C18 C17 H17A 119.9 . .
C16 C17 H17A 119.9 . .
C17 C18 C19 119.9(2) . .
C17 C18 H18A 120.0 . .
C19 C18 H18A 120.0 . .
C18 C19 C20 120.5(3) . .
C18 C19 H19A 119.8 . .
C20 C19 H19A 119.8 . .
C15 C20 C19 120.1(2) . .
C15 C20 H20A 119.9 . .
C19 C20 H20A 119.9 . .
O2 C21 H21A 109.5 . .
O2 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O2 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.357(2) .
O1 C1 1.396(2) .
O2 C6 1.370(2) .
O2 C21 1.424(3) .
N1 C13 1.340(3) .
N1 H2N1 0.90(3) .
N1 H1N1 0.98(3) .
N2 C14 1.147(2) .
C1 C10 1.369(3) .
C1 C2 1.395(3) .
C2 C3 1.361(3) .
C2 H2A 0.9500 .
C3 C4 1.414(3) .
C3 H3A 0.9500 .
C4 C9 1.412(3) .
C4 C5 1.418(3) .
C5 C6 1.357(3) .
C5 H5A 0.9500 .
C6 C7 1.405(3) .
C7 C8 1.358(3) .
C7 H7A 0.9500 .
C8 C9 1.416(3) .
C8 H8A 0.9500 .
C9 C10 1.430(3) .
C10 C11 1.511(2) .
C11 C12 1.517(2) .
C11 C15 1.525(3) .
C11 H11A 1.0000 .
C12 C13 1.354(3) .
C12 C14 1.410(3) .
C15 C16 1.382(3) .
C15 C20 1.384(3) .
C16 C17 1.385(3) .
C16 H16A 0.9500 .
C17 C18 1.361(4) .
C17 H17A 0.9500 .
C18 C19 1.368(4) .
C18 H18A 0.9500 .
C19 C20 1.387(3) .
C19 H19A 0.9500 .
C20 H20A 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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
C13 O1 C1 C10 6.0(3) . . . .
C13 O1 C1 C2 -175.08(17) . . . .
C10 C1 C2 C3 1.1(3) . . . .
O1 C1 C2 C3 -177.81(19) . . . .
C1 C2 C3 C4 -1.8(3) . . . .
C2 C3 C4 C9 0.1(3) . . . .
C2 C3 C4 C5 -179.5(2) . . . .
C9 C4 C5 C6 -0.4(3) . . . .
C3 C4 C5 C6 179.2(2) . . . .
C4 C5 C6 O2 179.3(2) . . . .
C4 C5 C6 C7 -1.4(3) . . . .
C21 O2 C6 C5 4.2(4) . . . .
C21 O2 C6 C7 -175.1(2) . . . .
C5 C6 C7 C8 2.3(4) . . . .
O2 C6 C7 C8 -178.32(19) . . . .
C6 C7 C8 C9 -1.3(3) . . . .
C3 C4 C9 C8 -178.3(2) . . . .
C5 C4 C9 C8 1.4(3) . . . .
C3 C4 C9 C10 2.3(3) . . . .
C5 C4 C9 C10 -178.02(19) . . . .
C7 C8 C9 C4 -0.5(3) . . . .
C7 C8 C9 C10 178.87(19) . . . .
C2 C1 C10 C9 1.3(3) . . . .
O1 C1 C10 C9 -179.89(17) . . . .
C2 C1 C10 C11 -176.58(19) . . . .
O1 C1 C10 C11 2.2(3) . . . .
C4 C9 C10 C1 -3.0(3) . . . .
C8 C9 C10 C1 177.66(19) . . . .
C4 C9 C10 C11 174.90(17) . . . .
C8 C9 C10 C11 -4.4(3) . . . .
C1 C10 C11 C12 -10.3(3) . . . .
C9 C10 C11 C12 171.89(17) . . . .
C1 C10 C11 C15 112.7(2) . . . .
C9 C10 C11 C15 -65.1(2) . . . .
C10 C11 C12 C13 12.1(3) . . . .
C15 C11 C12 C13 -112.7(2) . . . .
C10 C11 C12 C14 -170.12(17) . . . .
C15 C11 C12 C14 65.1(2) . . . .
C14 C12 C13 N1 -2.2(3) . . . .
C11 C12 C13 N1 175.63(19) . . . .
C14 C12 C13 O1 176.89(18) . . . .
C11 C12 C13 O1 -5.3(3) . . . .
C1 O1 C13 N1 174.75(17) . . . .
C1 O1 C13 C12 -4.5(3) . . . .
C13 C12 C14 N2 -178(100) . . . .
C11 C12 C14 N2 4(8) . . . .
C10 C11 C15 C16 144.82(18) . . . .
C12 C11 C15 C16 -92.3(2) . . . .
C10 C11 C15 C20 -39.0(2) . . . .
C12 C11 C15 C20 83.9(2) . . . .
C20 C15 C16 C17 -0.6(3) . . . .
C11 C15 C16 C17 175.65(19) . . . .
C15 C16 C17 C18 0.4(4) . . . .
C16 C17 C18 C19 0.2(4) . . . .
C17 C18 C19 C20 -0.4(4) . . . .
C16 C15 C20 C19 0.4(3) . . . .
C11 C15 C20 C19 -175.91(19) . . . .
C18 C19 C20 C15 0.2(4) . . . .
