#------------------------------------------------------------------------------
#$Date: 2023-05-23 11:11:30 +0300 (Tue, 23 May 2023) $
#$Revision: 283954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107248.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_8107248
loop_
_publ_author_name
'Zhang, Yu-Long'
'Liu, Shu-Lian'
'Hou, Gui-Ge'
'Wang, Lei'
'Zhang, Xiao-Fan'
_publ_section_title
;
 Crystal structure of
 (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one,
 C19H17BrO3
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              907
_journal_page_last               909
_journal_paper_doi               10.1515/ncrs-2022-0316
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 Br O3'
_chemical_formula_sum            'C19 H17 Br O3'
_chemical_formula_weight         373.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                93.634(11)
_cell_angle_beta                 90.609(9)
_cell_angle_gamma                118.201(11)
_cell_formula_units_Z            2
_cell_length_a                   8.2887(7)
_cell_length_b                   8.4190(12)
_cell_length_c                   13.1164(15)
_cell_measurement_reflns_used    2626
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4550
_cell_measurement_theta_min      2.8500
_cell_volume                     804.17(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5429
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.754
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.725
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.054(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0474P)²+2.9961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0316_suppl.cif
_cod_data_source_block           XF-2-11
_cod_database_code               8107248
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.783
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.06665(8) 0.74238(10) 0.21958(5) 0.0303(3) Uani 1 1 d . . . . .
C1 C 0.8426(8) 0.5624(8) 0.3815(4) 0.0195(13) Uani 1 1 d . . . . .
H1 H 0.771558 0.474543 0.330170 0.023 Uiso 1 1 calc R U . . .
C2 C 0.9975(8) 0.7158(8) 0.3582(4) 0.0206(13) Uani 1 1 d . . . . .
C3 C 1.1045(8) 0.8522(8) 0.4327(5) 0.0231(13) Uani 1 1 d . . . . .
H3 H 1.207276 0.955778 0.415461 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0539(8) 0.8295(8) 0.5334(5) 0.0217(13) Uani 1 1 d . . . . .
H4 H 1.124545 0.919343 0.584029 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8549(8) 0.6535(9) 0.6715(5) 0.0244(14) Uani 1 1 d . . . . .
H5A H 0.887366 0.771045 0.705500 0.029 Uiso 1 1 calc R U . . .
H5B H 0.928711 0.607489 0.703575 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6522(8) 0.5254(8) 0.6865(4) 0.0204(13) Uani 1 1 d . . . . .
H6A H 0.636370 0.496944 0.757402 0.024 Uiso 1 1 calc R U . . .
H6B H 0.580705 0.585603 0.671510 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5816(7) 0.3522(8) 0.6186(4) 0.0172(12) Uani 1 1 d . . . . .
C8 C 0.6324(8) 0.3708(8) 0.5091(4) 0.0153(12) Uani 1 1 d . . . . .
C9 C 0.7936(8) 0.5406(8) 0.4838(4) 0.0169(12) Uani 1 1 d . . . . .
C10 C 0.9000(8) 0.6756(8) 0.5605(4) 0.0198(13) Uani 1 1 d . . . . .
C11 C 0.4872(7) 0.1826(8) 0.6471(4) 0.0164(12) Uani 1 1 d . . . . .
H11 H 0.462205 0.091826 0.595573 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4174(7) 0.1188(7) 0.7476(4) 0.0158(12) Uani 1 1 d . . . . .
C13 C 0.4095(7) -0.0439(8) 0.7722(4) 0.0168(12) Uani 1 1 d . . . . .
H13 H 0.445886 -0.107472 0.725625 0.020 Uiso 1 1 calc R U . . .
C14 C 0.3474(7) -0.1101(8) 0.8657(4) 0.0171(12) Uani 1 1 d . . . . .
C15 C 0.2896(8) -0.0191(8) 0.9355(4) 0.0179(12) Uani 1 1 d . . . . .
H15 H 0.249605 -0.063302 0.998698 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2926(8) 0.1385(8) 0.9093(4) 0.0187(12) Uani 1 1 d . . . . .
C17 C 0.3555(8) 0.2097(8) 0.8166(4) 0.0171(12) Uani 1 1 d . . . . .
H17 H 0.356464 0.316094 0.800407 0.021 Uiso 1 1 calc R U . . .
C18 C 0.2627(9) -0.3543(9) 0.9729(5) 0.0281(15) Uani 1 1 d . . . . .
H18A H 0.331427 -0.277078 1.031810 0.042 Uiso 1 1 calc R U . . .
H18B H 0.262500 -0.468327 0.974168 0.042 Uiso 1 1 calc R U . . .
H18C H 0.139025 -0.373505 0.973577 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2004(8) 0.1908(8) 1.0759(4) 0.0214(13) Uani 1 1 d . . . . .
H19A H 0.102114 0.069609 1.077040 0.032 Uiso 1 1 calc R U . . .
H19B H 0.167062 0.273034 1.112066 0.032 Uiso 1 1 calc R U . . .
H19C H 0.308928 0.199309 1.108233 0.032 Uiso 1 1 calc R U . . .
O1 O 0.5450(6) 0.2496(6) 0.4420(3) 0.0240(10) Uani 1 1 d . . . . .
O2 O 0.3450(6) -0.2711(6) 0.8822(3) 0.0263(10) Uani 1 1 d . . . . .
O3 O 0.2345(6) 0.2361(6) 0.9728(3) 0.0252(10) 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'
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
C2 C1 C9 119.2(6) . .
C2 C1 H1 120.4 . .
C9 C1 H1 120.4 . .
C1 C2 C3 122.0(5) . .
C1 C2 Br1 119.0(5) . .
C3 C2 Br1 119.0(4) . .
C4 C3 C2 118.3(5) . .
C4 C3 H3 120.9 . .
C2 C3 H3 120.9 . .
C3 C4 C10 121.6(6) . .
C3 C4 H4 119.2 . .
C10 C4 H4 119.2 . .
C10 C5 C6 113.1(5) . .
C10 C5 H5A 109.0 . .
C6 C5 H5A 109.0 . .
C10 C5 H5B 109.0 . .
C6 C5 H5B 109.0 . .
H5A C5 H5B 107.8 . .
C7 C6 C5 112.0(5) . .
C7 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
C7 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C11 C7 C8 116.4(5) . .
C11 C7 C6 127.0(5) . .
C8 C7 C6 116.5(5) . .
O1 C8 C9 120.7(5) . .
O1 C8 C7 121.5(5) . .
C9 C8 C7 117.8(5) . .
C1 C9 C10 120.0(5) . .
C1 C9 C8 118.9(5) . .
C10 C9 C8 121.1(5) . .
C4 C10 C9 119.0(5) . .
C4 C10 C5 119.7(6) . .
C9 C10 C5 121.3(5) . .
C7 C11 C12 129.8(5) . .
C7 C11 H11 115.1 . .
C12 C11 H11 115.1 . .
C13 C12 C17 119.6(5) . .
C13 C12 C11 117.0(5) . .
C17 C12 C11 123.4(5) . .
C14 C13 C12 119.8(5) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
O2 C14 C13 115.2(5) . .
O2 C14 C15 123.8(5) . .
C13 C14 C15 121.0(5) . .
C16 C15 C14 118.7(5) . .
C16 C15 H15 120.6 . .
C14 C15 H15 120.6 . .
O3 C16 C15 122.8(5) . .
O3 C16 C17 115.3(5) . .
C15 C16 C17 121.8(5) . .
C16 C17 C12 119.0(5) . .
C16 C17 H17 120.5 . .
C12 C17 H17 120.5 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O3 C19 H19A 109.5 . .
O3 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O3 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C14 O2 C18 116.9(5) . .
C16 O3 C19 118.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.908(6) .
C1 C2 1.379(8) .
C1 C9 1.403(8) .
C1 H1 0.9300 .
C2 C3 1.391(9) .
C3 C4 1.387(8) .
C3 H3 0.9300 .
C4 C10 1.392(8) .
C4 H4 0.9300 .
C5 C10 1.507(8) .
C5 C6 1.532(8) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.510(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C11 1.344(8) .
C7 C8 1.498(7) .
C8 O1 1.230(7) .
C8 C9 1.484(8) .
C9 C10 1.404(9) .
C11 C12 1.475(7) .
C11 H11 0.9300 .
C12 C13 1.398(8) .
C12 C17 1.401(8) .
C13 C14 1.382(8) .
C13 H13 0.9300 .
C14 O2 1.377(7) .
C14 C15 1.386(8) .
C15 C16 1.380(8) .
C15 H15 0.9300 .
C16 O3 1.377(7) .
C16 C17 1.385(8) .
C17 H17 0.9300 .
C18 O2 1.429(7) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 O3 1.424(7) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C19 H19C O2 0.96 2.64 3.530(8) 154.9 2_657 yes
C18 H18B O3 0.96 2.39 3.344(8) 175.0 1_545 yes
C13 H13 O1 0.93 2.46 3.325(7) 155.7 2_656 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 C1 C2 C3 -1.6(9) . . . .
C9 C1 C2 Br1 178.6(4) . . . .
C1 C2 C3 C4 1.2(9) . . . .
Br1 C2 C3 C4 -179.0(4) . . . .
C2 C3 C4 C10 -0.3(9) . . . .
C10 C5 C6 C7 47.1(7) . . . .
C5 C6 C7 C11 130.1(6) . . . .
C5 C6 C7 C8 -45.6(7) . . . .
C11 C7 C8 O1 24.1(8) . . . .
C6 C7 C8 O1 -159.7(5) . . . .
C11 C7 C8 C9 -155.4(5) . . . .
C6 C7 C8 C9 20.8(7) . . . .
C2 C1 C9 C10 1.2(8) . . . .
C2 C1 C9 C8 -176.8(5) . . . .
O1 C8 C9 C1 1.3(8) . . . .
C7 C8 C9 C1 -179.1(5) . . . .
O1 C8 C9 C10 -176.6(5) . . . .
C7 C8 C9 C10 2.9(8) . . . .
C3 C4 C10 C9 -0.1(9) . . . .
C3 C4 C10 C5 177.5(5) . . . .
C1 C9 C10 C4 -0.3(8) . . . .
C8 C9 C10 C4 177.6(5) . . . .
C1 C9 C10 C5 -177.9(5) . . . .
C8 C9 C10 C5 0.1(8) . . . .
C6 C5 C10 C4 156.9(6) . . . .
C6 C5 C10 C9 -25.6(8) . . . .
C8 C7 C11 C12 -180.0(5) . . . .
C6 C7 C11 C12 4.3(10) . . . .
C7 C11 C12 C13 -148.3(6) . . . .
C7 C11 C12 C17 33.6(9) . . . .
C17 C12 C13 C14 -2.5(8) . . . .
C11 C12 C13 C14 179.3(5) . . . .
C12 C13 C14 O2 -180.0(5) . . . .
C12 C13 C14 C15 1.1(9) . . . .
O2 C14 C15 C16 -177.9(5) . . . .
C13 C14 C15 C16 0.9(9) . . . .
C14 C15 C16 O3 178.7(5) . . . .
C14 C15 C16 C17 -1.5(9) . . . .
O3 C16 C17 C12 179.9(5) . . . .
C15 C16 C17 C12 0.1(9) . . . .
C13 C12 C17 C16 2.0(8) . . . .
C11 C12 C17 C16 -179.9(5) . . . .
C13 C14 O2 C18 -173.2(5) . . . .
C15 C14 O2 C18 5.7(8) . . . .
C15 C16 O3 C19 11.3(8) . . . .
C17 C16 O3 C19 -168.6(5) . . . .
