Bending the bonds: unveiling halogen interactions in the elastic polymorph of 2,5-bis(3-bromophenyl)furan
Dyk, Konrad; Kinzhybalo, Vasyl; Horak, Yuriy; Butenko, Serhii; Siczek, Miłosz; Kamiński, Daniel M.; Journal of Applied Crystallography 57 (2024) –; doi:10.1107/S1600576723010609

data_2300729
_publ_section_title
;
 Bending the bonds: unveiling halogen interactions in the elastic
 polymorph of 2,5-bis(3-bromophenyl)furan
;
_journal_issue                   1
_journal_name_full               'Journal of Applied Crystallography'
_journal_paper_doi               10.1107/S1600576723010609
_journal_volume                  57
_journal_year                    2024
_chemical_formula_moiety         'C16 H10 Br2 O'
_chemical_formula_sum            'C16 H10 Br2 O'
_chemical_formula_weight         378.06
_chemical_melting_point          392
_chemical_name_common            MBFP
_chemical_name_systematic        2,5-bis(3-bromophenyl)furan
_chemical_properties_physical    'Metastable polymorph'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.97740(10)
_cell_length_b                   10.7746(2)
_cell_length_c                   31.2387(5)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0580
_cell_measurement_theta_min      2.8450
_cell_volume                     1338.73(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     49.00 131.00   0.50    0.13    --   83.00  16.00-107.44  164
  2  \w     89.00 132.00   0.50    0.13    --   83.00  35.00 -71.84   86
  3  \w     92.00 130.00   0.50    0.13    --   83.00  47.00 -48.28   76
  4  \w     91.00 128.00   0.50    0.13    --   83.00  56.00 138.82   74
  5  \w     29.00  60.00   0.50    0.13    --   74.41-126.00 -90.00   62
  6  \w     20.00  71.00   0.50    0.13    --   59.87 -95.00 -30.00  102
  7  \w     41.00  98.00   0.50    0.13    --   83.00-101.00  27.61  114
  8  \w     43.00 122.00   0.50    0.13    --   83.00  -1.00 -75.91  158
  9  \w     42.00 122.00   0.50    0.13    --   83.00  -2.00  -0.60  160
 10  \w     11.00  37.00   0.50    0.13    --   59.87 -30.00  90.00   52
 11  \w   -112.00 -75.00   0.50    0.13    --  -66.00 -52.00 161.61   74
 12  \w   -123.00 -87.00   0.50    0.13    --  -79.25 -58.00  88.57   72
 13  \w   -113.00 -75.00   0.50    0.13    --  -66.00 -44.00 102.37   76
 14  \w   -122.00 -86.00   0.50    0.13    --  -79.25 -61.00  22.29   72
 15  \w   -108.00 -71.00   0.50    0.13    --  -62.00 -49.00  29.49   74
 16  \w   -124.00 -76.00   0.50    0.13    --  -74.66 -30.00 -30.00   96
 17  \w     11.00  36.00   0.50    0.13    --   60.09 -30.00-150.00   50
 18  \w     11.00  36.00   0.50    0.13    --   60.09 -30.00 -60.00   50
 19  \w     11.00  36.00   0.50    0.13    --   60.09 -30.00 -30.00   50
 20  \w     80.00 105.00   0.50    0.13    --   79.13  30.00 -30.00   50
 21  \w     52.00  78.00   0.50    0.13    --   79.13-125.00 -60.00   52
 22  \w     95.00 121.00   0.50    0.13    --   79.13  30.00  30.00   52
 23  \w     99.00 124.00   0.50    0.13    --   79.13  30.00   0.00   50
 24  \w   -122.00 -96.00   0.50    0.13    --  -79.25 -56.00 -42.44   52
 25  \w     66.00 121.00   0.50    0.13    --   83.00  10.00 159.22  110
 26  \w     64.00  98.00   0.50    0.13    --   83.00-101.00 112.53   68
 27  \w     51.00  78.00   0.50    0.13    --   83.00 -69.00-149.94   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1182333000
_diffrn_orient_matrix_UB_12      0.0872025000
_diffrn_orient_matrix_UB_13      -0.0360723000
_diffrn_orient_matrix_UB_21      0.1648553000
_diffrn_orient_matrix_UB_22      -0.0857366000
_diffrn_orient_matrix_UB_23      -0.0334322000
_diffrn_orient_matrix_UB_31      -0.3298090000
_diffrn_orient_matrix_UB_32      -0.0740968000
_diffrn_orient_matrix_UB_33      -0.0038066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11796
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.685
_diffrn_reflns_theta_min         2.829
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       'Elastic Crystal'
_exptl_crystal_recrystallization_method
'Crystalization from the mixture of water and acetone 3:1 V/V'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.5992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2648
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ei5098sup1.cif
_cod_data_source_block           gamma
_cod_database_code               2300729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOBr
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.076
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.82(4)
 0.18(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C8(H8), C10(H10), C12(H12), C2(H2), C14(H14), C15(H15),
 C7(H7), C3(H3)
;
_shelx_res_checksum              37184
_shelx_hkl_checksum              75802
_olex2_exptl_crystal_mounting_method 'Mounted on polish nail'
_olex2_submission_original_sample_id 2,5-bis(3-bromophenyl)furan
_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.595
_cod_database_fobs_code 2300729