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#$Date: 2023-02-02 11:28:51 +0200 (Thu, 02 Feb 2023) $
#$Revision: 280759 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106669.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_8106669
loop_
_publ_author_name
'Yu, Yuanyuan'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C16H13BrN2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              761
_journal_page_last               762
_journal_paper_doi               10.1515/ncrs-2017-0022
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C16 H13 Br N2 O2'
_chemical_formula_sum            'C16 H13 Br N2 O2'
_chemical_formula_weight         345.19
_chemical_name_systematic
;
2-Amino-4-(4-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-
carbonitrile
;
_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                 109.162(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9109(14)
_cell_length_b                   11.1819(6)
_cell_length_c                   19.533(3)
_cell_measurement_reflns_used    1260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4070
_cell_measurement_theta_min      2.8270
_cell_volume                     2870.0(6)
_computing_cell_refinement       'Bruker FRAMBO [1]'
_computing_data_collection       'Bruker FRAMBO [1]'
_computing_data_reduction        'CrysAlisPro Version 1.171.36.28 [2]'
_computing_molecular_graphics    'Bruker SHELXTL [1]'
_computing_publication_material  'Bruker SHELXTL [1]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997) [3]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990) [1]'
_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       'φ and 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5247
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_exptl_absorpt_coefficient_mu    2.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0413
_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)+(0.0389P)²+1.8377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                1802
_reflns_number_total             2537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0022_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        2870.0(5)
_cod_original_sg_symbol_Hall     '-C2yc '
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106669
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 0.2808(3) 1.1609(3) 0.42823(18) 0.0261(8) Uani 1 1 d . . .
C2 C 0.2678(2) 1.0452(3) 0.44229(18) 0.0252(8) Uani 1 1 d . . .
C3 C 0.1642(2) 0.9879(3) 0.42818(18) 0.0240(8) Uani 1 1 d . . .
H3A H 0.1614 0.9563 0.4743 0.029 Uiso 1 1 calc R . .
C4 C 0.0838(2) 1.0817(3) 0.40268(18) 0.0237(8) Uani 1 1 d . . .
C5 C 0.1029(3) 1.1944(3) 0.38832(18) 0.0266(8) Uani 1 1 d . . .
C6 C 0.0270(3) 1.2903(3) 0.3602(2) 0.0387(10) Uani 1 1 d . . .
H6A H 0.0446 1.3363 0.3240 0.046 Uiso 1 1 calc R . .
H6B H 0.0274 1.3438 0.3994 0.046 Uiso 1 1 calc R . .
C7 C -0.0785(3) 1.2371(3) 0.3268(3) 0.0567(13) Uani 1 1 d . . .
H7A H -0.1290 1.3002 0.3179 0.068 Uiso 1 1 calc R . .
H7B H -0.0838 1.2005 0.2807 0.068 Uiso 1 1 calc R . .
C8 C -0.0999(3) 1.1443(3) 0.3762(3) 0.0522(12) Uani 1 1 d . . .
H8A H -0.1046 1.1836 0.4193 0.063 Uiso 1 1 calc R . .
H8B H -0.1651 1.1071 0.3516 0.063 Uiso 1 1 calc R . .
C9 C -0.0200(3) 1.0495(3) 0.39848(19) 0.0309(8) Uani 1 1 d . . .
C10 C 0.3537(3) 0.9710(3) 0.4690(2) 0.0315(9) Uani 1 1 d . . .
C11 C 0.1488(2) 0.8837(3) 0.37521(18) 0.0235(8) Uani 1 1 d . . .
C12 C 0.1430(3) 0.7690(3) 0.3987(2) 0.0329(9) Uani 1 1 d . . .
H12A H 0.1445 0.7560 0.4461 0.040 Uiso 1 1 calc R . .
C13 C 0.1348(3) 0.6725(3) 0.3530(2) 0.0389(10) Uani 1 1 d . . .
H13A H 0.1310 0.5951 0.3692 0.047 Uiso 1 1 calc R . .
C14 C 0.1325(3) 0.6926(3) 0.2837(2) 0.0321(9) Uani 1 1 d . . .
C15 C 0.1358(3) 0.8055(3) 0.2579(2) 0.0390(10) Uani 1 1 d . . .
H15A H 0.1325 0.8180 0.2101 0.047 Uiso 1 1 calc R . .
C16 C 0.1442(3) 0.9006(3) 0.3047(2) 0.0347(9) Uani 1 1 d . . .
H16A H 0.1468 0.9780 0.2879 0.042 Uiso 1 1 calc R . .
O1 O 0.20010(17) 1.23635(18) 0.39944(13) 0.0310(6) Uani 1 1 d . . .
O2 O -0.03949(18) 0.9499(2) 0.41529(15) 0.0429(7) Uani 1 1 d . . .
N1 N 0.3692(2) 1.2193(2) 0.44002(17) 0.0390(8) Uani 1 1 d . . .
H1A H 0.4260 1.1821 0.4586 0.047 Uiso 1 1 calc R . .
H1B H 0.3690 1.2938 0.4290 0.047 Uiso 1 1 calc R . .
N2 N 0.4207(2) 0.9057(3) 0.4896(2) 0.0496(9) Uani 1 1 d . . .
Br1 Br 0.12798(3) 0.55869(4) 0.22300(3) 0.0586(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
N1 C1 C2 127.5(3) . .
N1 C1 O1 110.6(3) . .
C2 C1 O1 121.9(3) . .
C1 C2 C10 119.1(3) . .
C1 C2 C3 123.5(3) . .
C10 C2 C3 117.3(3) . .
C4 C3 C2 109.1(2) . .
C4 C3 C11 112.7(3) . .
C2 C3 C11 111.0(3) . .
C4 C3 H3A 107.9 . .
C2 C3 H3A 107.9 . .
C11 C3 H3A 107.9 . .
C5 C4 C9 118.7(3) . .
C5 C4 C3 123.5(3) . .
C9 C4 C3 117.6(3) . .
C4 C5 O1 122.7(3) . .
C4 C5 C6 126.5(3) . .
O1 C5 C6 110.8(3) . .
C5 C6 C7 110.3(3) . .
C5 C6 H6A 109.6 . .
C7 C6 H6A 109.6 . .
C5 C6 H6B 109.6 . .
C7 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C8 C7 C6 111.1(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 112.9(3) . .
C9 C8 H8A 109.0 . .
C7 C8 H8A 109.0 . .
C9 C8 H8B 109.0 . .
C7 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
O2 C9 C4 120.9(3) . .
O2 C9 C8 121.2(3) . .
C4 C9 C8 117.9(3) . .
N2 C10 C2 176.6(4) . .
C16 C11 C12 118.4(3) . .
C16 C11 C3 121.8(3) . .
C12 C11 C3 119.8(3) . .
C11 C12 C13 121.0(3) . .
C11 C12 H12A 119.5 . .
C13 C12 H12A 119.5 . .
C14 C13 C12 118.9(3) . .
C14 C13 H13A 120.5 . .
C12 C13 H13A 120.5 . .
C13 C14 C15 121.8(3) . .
C13 C14 Br1 118.4(3) . .
C15 C14 Br1 119.8(3) . .
C14 C15 C16 118.2(4) . .
C14 C15 H15A 120.9 . .
C16 C15 H15A 120.9 . .
C11 C16 C15 121.6(3) . .
C11 C16 H16A 119.2 . .
C15 C16 H16A 119.2 . .
C1 O1 C5 119.0(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 1.343(4) .
C1 C2 1.348(4) .
C1 O1 1.369(4) .
C2 C10 1.406(5) .
C2 C3 1.516(4) .
C3 C4 1.495(4) .
C3 C11 1.526(4) .
C3 H3A 0.9800 .
C4 C5 1.337(4) .
C4 C9 1.464(5) .
C5 O1 1.380(4) .
C5 C6 1.478(4) .
C6 C7 1.518(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.511(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.493(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.217(4) .
C10 N2 1.148(4) .
C11 C16 1.371(5) .
C11 C12 1.374(4) .
C12 C13 1.381(5) .
C12 H12A 0.9300 .
C13 C14 1.361(5) .
C13 H13A 0.9300 .
C14 C15 1.366(5) .
C14 Br1 1.898(3) .
C15 C16 1.381(5) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
