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#$Date: 2023-01-12 12:14:35 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280299 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106449.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_8106449
loop_
_publ_author_name
'Yu, Xue-Jun'
'Zhao, Lin-Ping'
'Ma, Long-Ji'
'Gong, Hua-Fen'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile,
 C16H11BrN2O3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              109
_journal_page_last               110
_journal_paper_doi               10.1515/ncrs-2016-0172
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C16 H11 Br N2 O3'
_chemical_formula_sum            'C16 H11 Br N2 O3'
_chemical_formula_weight         359.17
_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                 110.511(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.504(3)
_cell_length_b                   8.2788(10)
_cell_length_c                   18.170(3)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4508
_cell_measurement_theta_min      2.0223
_cell_volume                     3029.7(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9161
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.727
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0429
_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)+(0.0709P)²+2.7884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2213
_reflns_number_total             2663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0172_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        3029.8(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106449
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 -0.15561(14) 0.7447(4) -0.23949(17) 0.0474(7) Uani 1 1 d . . .
C2 C -0.16301(14) 0.8920(3) -0.20193(17) 0.0432(6) Uani 1 1 d . . .
C3 C -0.15003(15) 1.0332(3) -0.23085(18) 0.0472(7) Uani 1 1 d . . .
C4 C -0.12421(19) 1.0379(4) -0.2927(2) 0.0598(9) Uani 1 1 d . . .
H4A H -0.1156 1.1363 -0.3119 0.072 Uiso 1 1 calc R . .
C5 C -0.11255(18) 0.9000(4) -0.3229(2) 0.0593(8) Uani 1 1 d . . .
C6 C -0.0816(2) 0.8764(6) -0.3836(3) 0.0862(13) Uani 1 1 d . . .
H6A H -0.0710 0.9796 -0.4002 0.129 Uiso 1 1 calc R . .
H6B H -0.1121 0.8204 -0.4278 0.129 Uiso 1 1 calc R . .
H6C H -0.0417 0.8139 -0.3619 0.129 Uiso 1 1 calc R . .
C7 C -0.18528(14) 1.1865(3) -0.14360(17) 0.0462(7) Uani 1 1 d . . .
C8 C -0.19815(14) 1.0511(3) -0.10985(17) 0.0424(6) Uani 1 1 d . . .
C9 C -0.18439(13) 0.8813(3) -0.13198(17) 0.0419(6) Uani 1 1 d . . .
H9A H -0.2256 0.8188 -0.1466 0.050 Uiso 1 1 calc R . .
C10 C -0.22607(16) 1.0648(3) -0.0507(2) 0.0507(7) Uani 1 1 d . . .
C11 C -0.13245(13) 0.7989(3) -0.06265(16) 0.0406(6) Uani 1 1 d . . .
C12 C -0.06519(14) 0.8254(4) -0.04449(18) 0.0518(7) Uani 1 1 d . . .
H12A H -0.0512 0.8939 -0.0761 0.062 Uiso 1 1 calc R . .
C13 C -0.01846(15) 0.7528(4) 0.01928(19) 0.0589(8) Uani 1 1 d . . .
H13A H 0.0266 0.7709 0.0301 0.071 Uiso 1 1 calc R . .
C14 C -0.03920(15) 0.6534(4) 0.06666(18) 0.0534(7) Uani 1 1 d . . .
C15 C -0.10578(17) 0.6263(4) 0.0509(2) 0.0589(8) Uani 1 1 d . . .
H15A H -0.1196 0.5600 0.0836 0.071 Uiso 1 1 calc R . .
C16 C -0.15181(15) 0.6982(4) -0.01385(19) 0.0518(7) Uani 1 1 d . . .
H16A H -0.1968 0.6786 -0.0249 0.062 Uiso 1 1 calc R . .
O1 O -0.15946(12) 1.1804(2) -0.20255(13) 0.0556(5) Uani 1 1 d . . .
O2 O -0.12832(12) 0.7553(3) -0.29775(13) 0.0585(6) Uani 1 1 d . . .
O3 O -0.17084(11) 0.6110(3) -0.22451(13) 0.0578(6) Uani 1 1 d . . .
N1 N -0.19546(15) 1.3389(3) -0.12754(18) 0.0633(8) Uani 1 1 d . . .
H1A H -0.2121 1.3599 -0.0919 0.076 Uiso 1 1 calc R . .
H1B H -0.1854 1.4165 -0.1528 0.076 Uiso 1 1 calc R . .
N2 N -0.24789(19) 1.0700(3) -0.0018(2) 0.0748(10) Uani 1 1 d . . .
Br1 Br 0.02508(2) 0.55281(5) 0.15404(2) 0.0848(2) 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'
Br Br -0.2901 2.4595 '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
O3 C1 O2 116.8(3) . .
O3 C1 C2 125.9(3) . .
O2 C1 C2 117.3(3) . .
C3 C2 C1 118.6(3) . .
C3 C2 C9 123.2(3) . .
C1 C2 C9 118.2(2) . .
C2 C3 O1 123.2(3) . .
C2 C3 C4 121.6(3) . .
O1 C3 C4 115.1(2) . .
C5 C4 C3 119.1(3) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
C4 C5 O2 120.7(3) . .
C4 C5 C6 128.1(3) . .
O2 C5 C6 111.1(3) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N1 C7 C8 127.7(3) . .
N1 C7 O1 110.4(2) . .
C8 C7 O1 121.9(3) . .
C7 C8 C10 119.3(3) . .
C7 C8 C9 123.9(2) . .
C10 C8 C9 116.8(2) . .
C2 C9 C8 108.4(2) . .
C2 C9 C11 112.0(2) . .
C8 C9 C11 110.5(2) . .
C2 C9 H9A 108.6 . .
C8 C9 H9A 108.6 . .
C11 C9 H9A 108.6 . .
N2 C10 C8 177.3(3) . .
C16 C11 C12 117.8(3) . .
C16 C11 C9 120.2(2) . .
C12 C11 C9 122.0(2) . .
C13 C12 C11 121.7(3) . .
C13 C12 H12A 119.2 . .
C11 C12 H12A 119.2 . .
C14 C13 C12 119.1(3) . .
C14 C13 H13A 120.4 . .
C12 C13 H13A 120.4 . .
C13 C14 C15 120.6(3) . .
C13 C14 Br1 119.1(2) . .
C15 C14 Br1 120.2(2) . .
C14 C15 C16 119.4(3) . .
C14 C15 H15A 120.3 . .
C16 C15 H15A 120.3 . .
C15 C16 C11 121.3(3) . .
C15 C16 H16A 119.3 . .
C11 C16 H16A 119.3 . .
C3 O1 C7 118.8(2) . .
C5 O2 C1 122.2(2) . .
C7 N1 H1A 120.0 . .
C7 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 O3 1.212(4) .
C1 O2 1.381(4) .
C1 C2 1.433(4) .
C2 C3 1.350(4) .
C2 C9 1.498(4) .
C3 O1 1.366(4) .
C3 C4 1.417(4) .
C4 C5 1.328(5) .
C4 H4A 0.9300 .
C5 O2 1.366(4) .
C5 C6 1.488(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N1 1.331(4) .
C7 C8 1.352(4) .
C7 O1 1.369(3) .
C8 C10 1.407(4) .
C8 C9 1.519(4) .
C9 C11 1.521(4) .
C9 H9A 0.9800 .
C10 N2 1.143(4) .
C11 C16 1.383(4) .
C11 C12 1.384(4) .
C12 C13 1.377(5) .
C12 H12A 0.9300 .
C13 C14 1.373(5) .
C13 H13A 0.9300 .
C14 C15 1.377(5) .
C14 Br1 1.894(3) .
C15 C16 1.379(4) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
