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#$Date: 2023-03-13 11:00:35 +0200 (Mon, 13 Mar 2023) $
#$Revision: 281835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106923.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_8106923
loop_
_publ_author_name
'Qu, Ying-Juan'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3-phenoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C22H18N2O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              505
_journal_page_last               506
_journal_paper_doi               10.1515/ncrs-2015-0168
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C22 H18 N2 O3'
_chemical_formula_sum            'C22 H18 N2 O3'
_chemical_formula_weight         358.38
_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
_cell_angle_alpha                80.085(8)
_cell_angle_beta                 79.197(10)
_cell_angle_gamma                81.655(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5476(10)
_cell_length_b                   8.7361(10)
_cell_length_c                   13.0076(12)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1880
_cell_measurement_theta_min      2.6610
_cell_volume                     933.43(18)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6044
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.068(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0940P)²+0.0123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1886
_reflns_number_gt                2239
_reflns_number_total             3297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0168_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106923
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
C1 C 0.4370(2) 0.6261(2) 0.61095(16) 0.0395(5) Uani 1 1 d . . .
C2 C 0.3030(2) 0.7174(2) 0.58706(16) 0.0393(5) Uani 1 1 d . . .
C3 C 0.1376(2) 0.6630(2) 0.61948(16) 0.0375(5) Uani 1 1 d . . .
H3A H 0.0798 0.6949 0.5595 0.045 Uiso 1 1 calc R . .
C4 C 0.1569(2) 0.4876(2) 0.64282(15) 0.0367(5) Uani 1 1 d . . .
C5 C 0.2954(2) 0.4039(2) 0.66189(16) 0.0401(5) Uani 1 1 d . . .
C6 C 0.3212(3) 0.2314(2) 0.69273(19) 0.0505(6) Uani 1 1 d . . .
H6A H 0.3880 0.2065 0.7473 0.061 Uiso 1 1 calc R . .
H6B H 0.3767 0.1835 0.6320 0.061 Uiso 1 1 calc R . .
C7 C 0.1623(3) 0.1653(3) 0.7336(2) 0.0599(7) Uani 1 1 d . . .
H7A H 0.1793 0.0522 0.7382 0.072 Uiso 1 1 calc R . .
H7B H 0.1206 0.1905 0.8041 0.072 Uiso 1 1 calc R . .
C8 C 0.0417(3) 0.2315(3) 0.6612(2) 0.0623(7) Uani 1 1 d . . .
H8A H 0.0765 0.1921 0.5943 0.075 Uiso 1 1 calc R . .
H8B H -0.0608 0.1947 0.6927 0.075 Uiso 1 1 calc R . .
C9 C 0.0198(2) 0.4058(2) 0.64066(16) 0.0428(5) Uani 1 1 d . . .
C10 C 0.3145(2) 0.8715(3) 0.53409(18) 0.0444(6) Uani 1 1 d . . .
C11 C 0.0409(2) 0.7351(2) 0.71333(17) 0.0409(5) Uani 1 1 d . . .
C12 C -0.0937(2) 0.8405(3) 0.7013(2) 0.0553(7) Uani 1 1 d . . .
H12A H -0.1266 0.8661 0.6356 0.066 Uiso 1 1 calc R . .
C13 C -0.1794(3) 0.9079(3) 0.7861(3) 0.0772(9) Uani 1 1 d . . .
H13A H -0.2697 0.9790 0.7770 0.093 Uiso 1 1 calc R . .
C14 C -0.1337(3) 0.8718(4) 0.8833(3) 0.0791(9) Uani 1 1 d . . .
H14A H -0.1909 0.9189 0.9400 0.095 Uiso 1 1 calc R . .
C15 C -0.0015(3) 0.7645(3) 0.8958(2) 0.0673(7) Uani 1 1 d . . .
C16 C 0.0859(2) 0.6971(3) 0.81204(18) 0.0523(6) Uani 1 1 d . . .
H16A H 0.1757 0.6255 0.8217 0.063 Uiso 1 1 calc R . .
C17 C 0.1881(3) 0.7094(4) 1.0143(2) 0.0698(8) Uani 1 1 d . . .
C18 C 0.2287(5) 0.6004(5) 1.0991(3) 0.1076(12) Uani 1 1 d . . .
H18A H 0.1549 0.5360 1.1392 0.129 Uiso 1 1 calc R . .
C19 C 0.3814(7) 0.5901(6) 1.1225(3) 0.1356(17) Uani 1 1 d . . .
H19A H 0.4114 0.5164 1.1781 0.163 Uiso 1 1 calc R . .
C20 C 0.4864(5) 0.6847(6) 1.0663(4) 0.1244(16) Uani 1 1 d . . .
H20A H 0.5876 0.6791 1.0842 0.149 Uiso 1 1 calc R . .
C21 C 0.4453(4) 0.7882(5) 0.9837(3) 0.1044(12) Uani 1 1 d . . .
H21A H 0.5204 0.8511 0.9437 0.125 Uiso 1 1 calc R . .
C22 C 0.2966(3) 0.8032(4) 0.9571(2) 0.0760(8) Uani 1 1 d . . .
H22A H 0.2699 0.8768 0.9005 0.091 Uiso 1 1 calc R . .
O1 O 0.43341(15) 0.47230(16) 0.65525(12) 0.0478(4) Uani 1 1 d . . .
O2 O -0.10621(16) 0.47895(18) 0.61951(13) 0.0551(5) Uani 1 1 d . . .
O3 O 0.0328(2) 0.7192(3) 0.99768(16) 0.1053(9) Uani 1 1 d . . .
N1 N 0.58526(19) 0.6661(2) 0.59722(16) 0.0569(6) Uani 1 1 d . . .
H1A H 0.6038 0.7600 0.5702 0.068 Uiso 1 1 calc R . .
H1B H 0.6622 0.5979 0.6154 0.068 Uiso 1 1 calc R . .
N2 N 0.3208(2) 0.9961(2) 0.48953(18) 0.0638(6) 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
N1 C1 C2 127.85(19) . .
N1 C1 O1 110.68(15) . .
C2 C1 O1 121.47(17) . .
C1 C2 C10 119.50(17) . .
C1 C2 C3 122.39(18) . .
C10 C2 C3 118.05(16) . .
C4 C3 C11 111.37(16) . .
C4 C3 C2 108.49(15) . .
C11 C3 C2 112.13(16) . .
C4 C3 H3A 108.2 . .
C11 C3 H3A 108.2 . .
C2 C3 H3A 108.2 . .
C5 C4 C9 119.20(19) . .
C5 C4 C3 122.55(17) . .
C9 C4 C3 118.21(16) . .
C4 C5 O1 122.29(18) . .
C4 C5 C6 125.81(18) . .
O1 C5 C6 111.90(16) . .
C5 C6 C7 110.87(17) . .
C5 C6 H6A 109.5 . .
C7 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C7 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C8 C7 C6 110.9(2) . .
C8 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.0 . .
C9 C8 C7 113.38(19) . .
C9 C8 H8A 108.9 . .
C7 C8 H8A 108.9 . .
C9 C8 H8B 108.9 . .
C7 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
O2 C9 C4 120.62(19) . .
O2 C9 C8 121.65(18) . .
C4 C9 C8 117.70(17) . .
N2 C10 C2 178.2(2) . .
C12 C11 C16 118.8(2) . .
C12 C11 C3 120.4(2) . .
C16 C11 C3 120.80(17) . .
C13 C12 C11 120.3(3) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C14 C13 C12 120.9(2) . .
C14 C13 H13A 119.6 . .
C12 C13 H13A 119.6 . .
C13 C14 C15 118.9(2) . .
C13 C14 H14A 120.6 . .
C15 C14 H14A 120.6 . .
C16 C15 C14 121.0(3) . .
C16 C15 O3 121.4(2) . .
C14 C15 O3 117.4(2) . .
C15 C16 C11 120.1(2) . .
C15 C16 H16A 119.9 . .
C11 C16 H16A 119.9 . .
C22 C17 O3 124.0(3) . .
C22 C17 C18 120.1(3) . .
O3 C17 C18 115.8(3) . .
C19 C18 C17 118.4(4) . .
C19 C18 H18A 120.8 . .
C17 C18 H18A 120.8 . .
C20 C19 C18 120.8(4) . .
C20 C19 H19A 119.6 . .
C18 C19 H19A 119.6 . .
C19 C20 C21 119.8(4) . .
C19 C20 H20A 120.1 . .
C21 C20 H20A 120.1 . .
C20 C21 C22 121.8(3) . .
C20 C21 H21A 119.1 . .
C22 C21 H21A 119.1 . .
C17 C22 C21 119.1(3) . .
C17 C22 H22A 120.5 . .
C21 C22 H22A 120.5 . .
C1 O1 C5 118.92(14) . .
C17 O3 C15 119.5(2) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.335(2) .
C1 C2 1.352(3) .
C1 O1 1.370(2) .
C2 C10 1.411(3) .
C2 C3 1.518(3) .
C3 C4 1.501(3) .
C3 C11 1.518(3) .
C3 H3A 0.9800 .
C4 C5 1.339(3) .
C4 C9 1.466(3) .
C5 O1 1.380(2) .
C5 C6 1.486(3) .
C6 C7 1.521(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.512(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.490(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.222(2) .
C10 N2 1.146(3) .
C11 C12 1.381(3) .
C11 C16 1.381(3) .
C12 C13 1.376(4) .
C12 H12A 0.9300 .
C13 C14 1.365(4) .
C13 H13A 0.9300 .
C14 C15 1.375(4) .
C14 H14A 0.9300 .
C15 C16 1.372(3) .
C15 O3 1.389(3) .
C16 H16A 0.9300 .
C17 C22 1.356(4) .
C17 O3 1.372(3) .
C17 C18 1.389(5) .
C18 C19 1.382(6) .
C18 H18A 0.9300 .
C19 C20 1.336(5) .
C19 H19A 0.9300 .
C20 C21 1.345(5) .
C20 H20A 0.9300 .
C21 C22 1.361(4) .
C21 H21A 0.9300 .
C22 H22A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
