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#$Date: 2023-04-20 12:22:30 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107104.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_8107104
loop_
_publ_author_name
'Luo, Yunchun'
'Yi, Wen'
'Yao, Yuzhou'
'Zhu, Ni'
'Qin, Pengfei'
_publ_section_title
;
 The crystal structure of
 2-amino-4-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C16H13N3O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1077
_journal_page_last               1078
_journal_paper_doi               10.1515/ncrs-2016-0063
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C16 H13 N3 O4'
_chemical_formula_sum            'C16 H13 N3 O4'
_chemical_formula_weight         311.29
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.491(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.8536(12)
_cell_length_b                   11.0922(7)
_cell_length_c                   20.432(2)
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1430
_cell_measurement_theta_min      3.5000
_cell_volume                     2977.6(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5300
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0533
_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)+(0.0665P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                1612
_reflns_number_total             2630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0063_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        2977.6(4)
_cod_original_sg_symbol_Hall     '-C2yc '
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8107104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.28139(18) 0.6659(2) 0.43156(12) 0.0425(6) Uani 1 1 d . . .
C2 C 0.26607(17) 0.54934(19) 0.44472(12) 0.0410(6) Uani 1 1 d . . .
C3 C 0.16180(17) 0.49328(18) 0.42857(12) 0.0401(6) Uani 1 1 d . . .
H3A H 0.1554 0.4605 0.4716 0.048 Uiso 1 1 calc R . .
C4 C 0.08253(18) 0.58851(18) 0.40315(12) 0.0415(6) Uani 1 1 d . . .
C5 C 0.10368(17) 0.7018(2) 0.39009(12) 0.0448(6) Uani 1 1 d . . .
C6 C 0.02913(19) 0.7992(2) 0.36293(15) 0.0600(8) Uani 1 1 d . . .
H6A H 0.0490 0.8455 0.3290 0.072 Uiso 1 1 calc R . .
H6B H 0.0287 0.8530 0.4002 0.072 Uiso 1 1 calc R . .
C7 C -0.0764(2) 0.7482(3) 0.33002(19) 0.0868(11) Uani 1 1 d . . .
H7A H -0.1260 0.8129 0.3218 0.104 Uiso 1 1 calc R . .
H7B H -0.0808 0.7126 0.2858 0.104 Uiso 1 1 calc R . .
C8 C -0.1013(2) 0.6543(2) 0.3753(2) 0.0887(11) Uani 1 1 d . . .
H8A H -0.1078 0.6931 0.4162 0.106 Uiso 1 1 calc R . .
H8B H -0.1665 0.6181 0.3507 0.106 Uiso 1 1 calc R . .
C9 C -0.02312(18) 0.5574(2) 0.39671(14) 0.0530(7) Uani 1 1 d . . .
C10 C 0.35026(19) 0.4738(2) 0.47195(13) 0.0486(7) Uani 1 1 d . . .
C11 C 0.14793(16) 0.38958(18) 0.37728(12) 0.0377(6) Uani 1 1 d . . .
C12 C 0.13462(19) 0.27397(19) 0.39707(13) 0.0501(7) Uani 1 1 d . . .
H12A H 0.1304 0.2604 0.4410 0.060 Uiso 1 1 calc R . .
C13 C 0.12739(19) 0.1782(2) 0.35316(14) 0.0567(7) Uani 1 1 d . . .
H13A H 0.1186 0.1003 0.3672 0.068 Uiso 1 1 calc R . .
C14 C 0.13320(18) 0.1989(2) 0.28918(14) 0.0487(7) Uani 1 1 d . . .
C15 C 0.1440(2) 0.3131(2) 0.26668(14) 0.0587(7) Uani 1 1 d . . .
H15A H 0.1465 0.3260 0.2223 0.070 Uiso 1 1 calc R . .
C16 C 0.15119(19) 0.4080(2) 0.31136(13) 0.0554(7) Uani 1 1 d . . .
H16A H 0.1583 0.4859 0.2968 0.066 Uiso 1 1 calc R . .
O1 O 0.20223(12) 0.74254(13) 0.40217(9) 0.0505(5) Uani 1 1 d . . .
O2 O -0.04389(13) 0.45638(15) 0.41209(11) 0.0727(6) Uani 1 1 d . . .
O3 O 0.1369(3) 0.1106(2) 0.18894(15) 0.1443(13) Uani 1 1 d . . .
O4 O 0.1262(3) -0.0012(2) 0.26441(17) 0.1930(19) Uani 1 1 d . . .
N1 N 0.37054(15) 0.72362(17) 0.44523(11) 0.0577(6) Uani 1 1 d . . .
H1A H 0.4265 0.6858 0.4646 0.069 Uiso 1 1 calc R . .
H1B H 0.3718 0.7985 0.4346 0.069 Uiso 1 1 calc R . .
N2 N 0.41695(18) 0.4076(2) 0.49423(13) 0.0721(8) Uani 1 1 d . . .
N3 N 0.1304(2) 0.0956(2) 0.24350(16) 0.0752(8) 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 127.5(2) . .
N1 C1 O1 110.64(19) . .
C2 C1 O1 121.9(2) . .
C1 C2 C10 119.2(2) . .
C1 C2 C3 123.4(2) . .
C10 C2 C3 117.34(19) . .
C4 C3 C2 109.38(17) . .
C4 C3 C11 112.07(19) . .
C2 C3 C11 111.33(18) . .
C4 C3 H3A 108.0 . .
C2 C3 H3A 108.0 . .
C11 C3 H3A 108.0 . .
C5 C4 C9 118.6(2) . .
C5 C4 C3 123.4(2) . .
C9 C4 C3 117.85(19) . .
C4 C5 O1 122.5(2) . .
C4 C5 C6 126.3(2) . .
O1 C5 C6 111.16(19) . .
C5 C6 C7 110.9(2) . .
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 111.3(3) . .
C8 C7 H7A 109.4 . .
C6 C7 H7A 109.4 . .
C8 C7 H7B 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
C9 C8 C7 113.2(2) . .
C9 C8 H8A 108.9 . .
C7 C8 H8A 108.9 . .
C9 C8 H8B 108.9 . .
C7 C8 H8B 108.9 . .
H8A C8 H8B 107.8 . .
O2 C9 C4 120.1(2) . .
O2 C9 C8 121.9(2) . .
C4 C9 C8 117.9(2) . .
N2 C10 C2 177.1(2) . .
C12 C11 C16 118.4(2) . .
C12 C11 C3 120.0(2) . .
C16 C11 C3 121.57(19) . .
C13 C12 C11 121.2(2) . .
C13 C12 H12A 119.4 . .
C11 C12 H12A 119.4 . .
C14 C13 C12 119.0(2) . .
C14 C13 H13A 120.5 . .
C12 C13 H13A 120.5 . .
C13 C14 C15 121.8(2) . .
C13 C14 N3 118.9(2) . .
C15 C14 N3 119.3(3) . .
C14 C15 C16 118.5(2) . .
C14 C15 H15A 120.8 . .
C16 C15 H15A 120.8 . .
C15 C16 C11 121.2(2) . .
C15 C16 H16A 119.4 . .
C11 C16 H16A 119.4 . .
C1 O1 C5 118.93(17) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
O3 N3 O4 120.9(3) . .
O3 N3 C14 120.3(3) . .
O4 N3 C14 118.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.340(3) .
C1 C2 1.351(3) .
C1 O1 1.367(3) .
C2 C10 1.400(3) .
C2 C3 1.510(3) .
C3 C4 1.493(3) .
C3 C11 1.527(3) .
C3 H3A 0.9800 .
C4 C5 1.336(3) .
C4 C9 1.468(3) .
C5 O1 1.384(3) .
C5 C6 1.476(3) .
C6 C7 1.512(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.504(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.489(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.223(3) .
C10 N2 1.155(3) .
C11 C12 1.374(3) .
C11 C16 1.377(3) .
C12 C13 1.374(3) .
C12 H12A 0.9300 .
C13 C14 1.355(3) .
C13 H13A 0.9300 .
C14 C15 1.372(3) .
C14 N3 1.470(3) .
C15 C16 1.377(3) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
O3 N3 1.159(3) .
O4 N3 1.164(3) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
