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#$Date: 2022-11-15 11:08:26 +0200 (Tue, 15 Nov 2022) $
#$Revision: 279287 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106093.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_8106093
loop_
_publ_author_name
'Song, Jing'
_publ_section_title
;
 Crystal structural of
 2-amino-4-(3-bromophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran,
 C18H17BrN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              185
_journal_page_last               186
_journal_paper_doi               10.1515/ncrs-2017-0158
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 Br N2 O2'
_chemical_formula_sum            'C18 H17 Br N2 O2'
_chemical_formula_weight         373.24
_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                 93.372(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.554(2)
_cell_length_b                   9.3060(8)
_cell_length_c                   15.7691(15)
_cell_measurement_reflns_used    1454
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1670
_cell_measurement_theta_min      3.0210
_cell_volume                     3450.5(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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6281
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0064(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0521
_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)+(0.0955P)²+1.5645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                1887
_reflns_number_total             3028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0158_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106093
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 0.06428(16) 0.3210(4) 0.5128(2) 0.0338(9) Uani 1 1 d . . .
C2 C 0.04824(16) 0.2813(4) 0.4323(2) 0.0328(9) Uani 1 1 d . . .
C3 C 0.06737(16) 0.3616(4) 0.3556(2) 0.0351(9) Uani 1 1 d . . .
H3A H 0.0353 0.3666 0.3132 0.042 Uiso 1 1 calc R . .
C4 C 0.08275(15) 0.5120(4) 0.3831(2) 0.0331(9) Uani 1 1 d . . .
C5 C 0.09587(16) 0.5456(4) 0.4641(2) 0.0354(9) Uani 1 1 d . . .
C6 C 0.11692(19) 0.6875(4) 0.4957(3) 0.0435(10) Uani 1 1 d . . .
H6A H 0.1470 0.6727 0.5395 0.052 Uiso 1 1 calc R . .
H6B H 0.0862 0.7381 0.5211 0.052 Uiso 1 1 calc R . .
C7 C 0.13944(18) 0.7800(4) 0.4253(3) 0.0405(10) Uani 1 1 d . . .
C8 C 0.0968(2) 0.7750(4) 0.3491(3) 0.0486(11) Uani 1 1 d . . .
H8A H 0.0619 0.8212 0.3642 0.058 Uiso 1 1 calc R . .
H8B H 0.1118 0.8296 0.3031 0.058 Uiso 1 1 calc R . .
C9 C 0.08341(16) 0.6256(4) 0.3186(2) 0.0408(9) Uani 1 1 d . . .
C10 C 0.01731(16) 0.1516(4) 0.4182(2) 0.0344(9) Uani 1 1 d . . .
C11 C 0.1964(2) 0.7227(5) 0.3985(3) 0.0629(13) Uani 1 1 d . . .
H11A H 0.1916 0.6265 0.3773 0.094 Uiso 1 1 calc R . .
H11B H 0.2234 0.7225 0.4466 0.094 Uiso 1 1 calc R . .
H11C H 0.2102 0.7831 0.3548 0.094 Uiso 1 1 calc R . .
C12 C 0.1477(2) 0.9335(4) 0.4592(3) 0.0646(14) Uani 1 1 d . . .
H12A H 0.1620 0.9932 0.4157 0.097 Uiso 1 1 calc R . .
H12B H 0.1742 0.9326 0.5077 0.097 Uiso 1 1 calc R . .
H12C H 0.1118 0.9707 0.4753 0.097 Uiso 1 1 calc R . .
C13 C 0.11601(18) 0.2823(4) 0.3165(2) 0.0371(9) Uani 1 1 d . . .
C14 C 0.1049(2) 0.1922(5) 0.2478(3) 0.0557(12) Uani 1 1 d . . .
H14A H 0.0682 0.1877 0.2226 0.067 Uiso 1 1 calc R . .
C15 C 0.1467(3) 0.1095(5) 0.2162(3) 0.0703(15) Uani 1 1 d . . .
H15A H 0.1381 0.0480 0.1708 0.084 Uiso 1 1 calc R . .
C16 C 0.2012(3) 0.1169(5) 0.2511(3) 0.0680(15) Uani 1 1 d . . .
H16A H 0.2299 0.0620 0.2294 0.082 Uiso 1 1 calc R . .
C17 C 0.2126(2) 0.2082(5) 0.3195(3) 0.0536(12) Uani 1 1 d . . .
C18 C 0.17107(19) 0.2892(4) 0.3523(3) 0.0433(10) Uani 1 1 d . . .
H18A H 0.1796 0.3490 0.3986 0.052 Uiso 1 1 calc R . .
O1 O 0.09211(12) 0.4485(3) 0.52909(14) 0.0416(7) Uani 1 1 d . . .
O2 O 0.07150(14) 0.5978(3) 0.24419(18) 0.0595(9) Uani 1 1 d . . .
N1 N 0.05709(17) 0.2506(3) 0.5850(2) 0.0473(9) Uani 1 1 d . . .
H1A H 0.0403 0.1685 0.5838 0.057 Uiso 1 1 calc R . .
H1B H 0.0693 0.2872 0.6327 0.057 Uiso 1 1 calc R . .
N2 N -0.00881(16) 0.0499(4) 0.4038(2) 0.0507(9) Uani 1 1 d . . .
Br1 Br 0.28790(3) 0.21805(8) 0.36976(5) 0.0995(4) 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'
Br Br -0.2901 2.4595 '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 128.6(3) . .
N1 C1 O1 110.4(3) . .
C2 C1 O1 121.0(3) . .
C1 C2 C10 119.3(3) . .
C1 C2 C3 122.3(3) . .
C10 C2 C3 118.0(3) . .
C4 C3 C2 107.9(3) . .
C4 C3 C13 113.2(3) . .
C2 C3 C13 110.6(3) . .
C4 C3 H3A 108.4 . .
C2 C3 H3A 108.4 . .
C13 C3 H3A 108.4 . .
C5 C4 C9 118.9(3) . .
C5 C4 C3 122.2(3) . .
C9 C4 C3 118.9(3) . .
C4 C5 O1 122.6(3) . .
C4 C5 C6 125.6(3) . .
O1 C5 C6 111.7(3) . .
C5 C6 C7 112.4(3) . .
C5 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
C5 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C8 C7 C6 108.4(3) . .
C8 C7 C11 108.7(4) . .
C6 C7 C11 110.7(3) . .
C8 C7 C12 111.5(3) . .
C6 C7 C12 108.3(3) . .
C11 C7 C12 109.0(4) . .
C9 C8 C7 113.5(3) . .
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 120.2(3) . .
O2 C9 C8 122.6(3) . .
C4 C9 C8 117.1(3) . .
N2 C10 C2 176.9(4) . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C18 118.5(4) . .
C14 C13 C3 119.9(4) . .
C18 C13 C3 121.4(3) . .
C15 C14 C13 121.3(5) . .
C15 C14 H14A 119.4 . .
C13 C14 H14A 119.4 . .
C14 C15 C16 120.3(5) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C15 C16 C17 118.6(4) . .
C15 C16 H16A 120.7 . .
C17 C16 H16A 120.7 . .
C18 C17 C16 121.6(5) . .
C18 C17 Br1 119.3(4) . .
C16 C17 Br1 119.1(4) . .
C17 C18 C13 119.7(4) . .
C17 C18 H18A 120.1 . .
C13 C18 H18A 120.1 . .
C1 O1 C5 118.7(3) . .
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 1.332(5) .
C1 C2 1.355(5) .
C1 O1 1.373(4) .
C2 C10 1.421(5) .
C2 C3 1.512(5) .
C3 C4 1.503(5) .
C3 C13 1.524(5) .
C3 H3A 0.9800 .
C4 C5 1.334(5) .
C4 C9 1.468(5) .
C5 O1 1.373(4) .
C5 C6 1.486(5) .
C6 C7 1.523(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.520(6) .
C7 C11 1.527(6) .
C7 C12 1.533(5) .
C8 C9 1.499(6) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.218(4) .
C10 N2 1.144(4) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.382(6) .
C13 C18 1.385(6) .
C14 C15 1.367(7) .
C14 H14A 0.9300 .
C15 C16 1.368(7) .
C15 H15A 0.9300 .
C16 C17 1.387(7) .
C16 H16A 0.9300 .
C17 C18 1.361(6) .
C17 Br1 1.902(5) .
C18 H18A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
