#------------------------------------------------------------------------------
#$Date: 2023-06-21 12:08:25 +0300 (Wed, 21 Jun 2023) $
#$Revision: 284518 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107410.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_8107410
loop_
_publ_author_name
'Tang, Yun-Hao'
'Li, Fei'
'Yang, Yu-Zhu'
'Pan, Wei-Dong'
_publ_section_title
;
 Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene,
 C15H11BrO
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              257
_journal_page_last               258
_journal_paper_doi               10.1515/ncrs-2022-0584
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C15 H11 Br O'
_chemical_formula_sum            'C15 H11 Br O'
_chemical_formula_weight         287.15
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                104.938(10)
_cell_angle_beta                 104.246(12)
_cell_angle_gamma                97.021(10)
_cell_formula_units_Z            2
_cell_length_a                   6.0696(9)
_cell_length_b                   10.1112(10)
_cell_length_c                   10.9318(13)
_cell_measurement_reflns_used    1062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8410
_cell_measurement_theta_min      3.7500
_cell_volume                     615.82(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -9.00  83.00   1.00    7.50    --   15.65  77.00  30.00   92
  2  ω     17.00  42.00   1.00    7.50    --   15.65 -77.00 -90.00   25
  3  ω    -12.00  22.00   1.00    7.50    --  -16.43 -99.00-180.00   34
  4  ω    -55.00  42.00   1.00    7.50    --   15.65 -19.00-150.00   97
  5  ω    -20.00  15.00   1.00    7.50    --  -16.43 -99.00  60.00   35
  6  ω    -52.00  32.00   1.00    7.50    --   15.65 -57.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321684000
_diffrn_orient_matrix_UB_12      -0.0677075000
_diffrn_orient_matrix_UB_13      0.0052356000
_diffrn_orient_matrix_UB_21      0.0638397000
_diffrn_orient_matrix_UB_22      0.0235110000
_diffrn_orient_matrix_UB_23      0.0679415000
_diffrn_orient_matrix_UB_31      -0.1001060000
_diffrn_orient_matrix_UB_32      0.0187052000
_diffrn_orient_matrix_UB_33      0.0166901000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.014
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0573
_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)+(0.0472P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1383
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0584_suppl.cif
_cod_data_source_block           exp_12446
_cod_database_code               8107410
_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_max   0.712
_shelx_estimated_absorpt_t_min   0.398
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.604
_oxdiff_exptl_absorpt_empirical_full_min 0.630
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 0.00958(12) 0.71427(7) 0.47674(6) 0.0700(3) Uani 1 1 d . . . . .
O1 O 0.3547(10) 0.9778(5) 0.3253(5) 0.0957(18) Uani 1 1 d . . . . .
C1 C 0.1773(9) 0.7723(6) 0.3685(5) 0.0462(15) Uani 1 1 d . . . . .
C2 C 0.1967(10) 0.9235(6) 0.3821(6) 0.0569(17) Uani 1 1 d . . . . .
H2A H 0.0450 0.9396 0.3420 0.068 Uiso 1 1 calc R U . . .
H2B H 0.2413 0.9748 0.4755 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4405(10) 0.8910(6) 0.2364(5) 0.0498(15) Uani 1 1 d . . . . .
C4 C 0.5733(12) 0.9558(6) 0.1743(6) 0.0644(18) Uani 1 1 d . . . . .
H4 H 0.5947 1.0521 0.1905 0.077 Uiso 1 1 calc R U . . .
C5 C 0.6732(11) 0.8780(7) 0.0890(6) 0.0618(18) Uani 1 1 d . . . . .
H5 H 0.7627 0.9212 0.0470 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6410(11) 0.7368(7) 0.0661(6) 0.0612(18) Uani 1 1 d . . . . .
H6 H 0.7085 0.6837 0.0080 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5082(10) 0.6720(6) 0.1288(5) 0.0487(15) Uani 1 1 d . . . . .
H7 H 0.4899 0.5758 0.1128 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4013(9) 0.7476(5) 0.2152(5) 0.0372(13) Uani 1 1 d . . . . .
C9 C 0.2643(9) 0.6858(6) 0.2875(5) 0.0395(13) Uani 1 1 d . . . . .
C10 C 0.2237(9) 0.5307(5) 0.2651(5) 0.0388(13) Uani 1 1 d . . . . .
C11 C 0.0128(10) 0.4473(7) 0.1839(6) 0.0578(16) Uani 1 1 d . . . . .
H11 H -0.1027 0.4879 0.1436 0.069 Uiso 1 1 calc R U . . .
C12 C -0.0271(12) 0.3039(7) 0.1624(6) 0.0640(18) Uani 1 1 d . . . . .
H12 H -0.1685 0.2488 0.1073 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1411(12) 0.2436(6) 0.2220(6) 0.0549(17) Uani 1 1 d . . . . .
H13 H 0.1127 0.1477 0.2088 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3492(12) 0.3230(6) 0.3001(6) 0.0578(17) Uani 1 1 d . . . . .
H14 H 0.4633 0.2812 0.3398 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3934(11) 0.4663(6) 0.3213(6) 0.0527(15) Uani 1 1 d . . . . .
H15 H 0.5379 0.5195 0.3735 0.063 Uiso 1 1 calc R U . . .
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'
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
C3 O1 C2 121.1(5) . .
C2 C1 Br1 112.7(3) . .
C9 C1 Br1 123.3(4) . .
C9 C1 C2 124.0(5) . .
O1 C2 C1 115.1(4) . .
O1 C2 H2A 108.5 . .
O1 C2 H2B 108.5 . .
C1 C2 H2A 108.5 . .
C1 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
O1 C3 C4 116.1(5) . .
O1 C3 C8 121.3(5) . .
C4 C3 C8 122.5(5) . .
C3 C4 H4 120.1 . .
C5 C4 C3 119.8(5) . .
C5 C4 H4 120.1 . .
C4 C5 H5 120.2 . .
C6 C5 C4 119.7(6) . .
C6 C5 H5 120.2 . .
C5 C6 H6 119.8 . .
C5 C6 C7 120.4(5) . .
C7 C6 H6 119.8 . .
C6 C7 H7 119.2 . .
C6 C7 C8 121.6(5) . .
C8 C7 H7 119.2 . .
C3 C8 C7 116.0(5) . .
C3 C8 C9 119.8(4) . .
C7 C8 C9 124.2(5) . .
C1 C9 C8 117.0(5) . .
C1 C9 C10 123.4(5) . .
C8 C9 C10 119.6(4) . .
C11 C10 C9 119.9(5) . .
C15 C10 C9 121.9(5) . .
C15 C10 C11 118.1(5) . .
C10 C11 H11 119.7 . .
C12 C11 C10 120.5(6) . .
C12 C11 H11 119.7 . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.1(6) . .
C13 C12 H12 120.0 . .
C12 C13 H13 119.9 . .
C14 C13 C12 120.2(6) . .
C14 C13 H13 119.9 . .
C13 C14 H14 119.7 . .
C13 C14 C15 120.5(6) . .
C15 C14 H14 119.7 . .
C10 C15 C14 120.5(6) . .
C10 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.894(5) .
O1 C2 1.395(7) .
O1 C3 1.381(6) .
C1 C2 1.485(8) .
C1 C9 1.331(6) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.382(7) .
C3 C8 1.388(7) .
C4 H4 0.9300 .
C4 C5 1.368(8) .
C5 H5 0.9300 .
C5 C6 1.365(8) .
C6 H6 0.9300 .
C6 C7 1.387(7) .
C7 H7 0.9300 .
C7 C8 1.396(6) .
C8 C9 1.469(7) .
C9 C10 1.503(7) .
C10 C11 1.389(7) .
C10 C15 1.386(7) .
C11 H11 0.9300 .
C11 C12 1.388(8) .
C12 H12 0.9300 .
C12 C13 1.367(8) .
C13 H13 0.9300 .
C13 C14 1.356(8) .
C14 H14 0.9300 .
C14 C15 1.387(8) .
C15 H15 0.9300 .
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
Br1 C1 C2 O1 168.1(4) . . . .
Br1 C1 C9 C8 -176.7(4) . . . .
Br1 C1 C9 C10 4.9(8) . . . .
O1 C3 C4 C5 177.2(6) . . . .
O1 C3 C8 C7 -176.4(5) . . . .
O1 C3 C8 C9 0.5(8) . . . .
C1 C9 C10 C11 77.1(7) . . . .
C1 C9 C10 C15 -104.2(6) . . . .
C2 O1 C3 C4 172.4(6) . . . .
C2 O1 C3 C8 -9.9(9) . . . .
C2 C1 C9 C8 4.4(8) . . . .
C2 C1 C9 C10 -173.9(5) . . . .
C3 O1 C2 C1 15.3(9) . . . .
C3 C4 C5 C6 -0.1(10) . . . .
C3 C8 C9 C1 2.0(8) . . . .
C3 C8 C9 C10 -179.6(5) . . . .
C4 C3 C8 C7 1.2(9) . . . .
C4 C3 C8 C9 178.1(5) . . . .
C4 C5 C6 C7 -0.1(10) . . . .
C5 C6 C7 C8 0.9(9) . . . .
C6 C7 C8 C3 -1.4(8) . . . .
C6 C7 C8 C9 -178.1(5) . . . .
C7 C8 C9 C1 178.7(5) . . . .
C7 C8 C9 C10 -2.9(8) . . . .
C8 C3 C4 C5 -0.5(10) . . . .
C8 C9 C10 C11 -101.2(6) . . . .
C8 C9 C10 C15 77.5(6) . . . .
C9 C1 C2 O1 -13.0(9) . . . .
C9 C10 C11 C12 -179.9(5) . . . .
C9 C10 C15 C14 179.1(5) . . . .
C10 C11 C12 C13 0.5(9) . . . .
C11 C10 C15 C14 -2.2(8) . . . .
C11 C12 C13 C14 -1.4(9) . . . .
C12 C13 C14 C15 0.5(9) . . . .
C13 C14 C15 C10 1.4(9) . . . .
C15 C10 C11 C12 1.3(8) . . . .
