#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:18:19 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281448 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246101.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_7246101
loop_
_publ_author_name
'Dyk, Konrad'
'Kinzhybalo, Vasyl'
'Czernel, Grzegorz'
'Grudziński, Wojciech'
'Horak, Yuriy'
'Butenko, Serhii'
'Kamiński, Daniel M.'
_publ_section_title
;
 Solvent induced conformational polymorphism
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              971
_journal_page_last               980
_journal_paper_doi               10.1039/D2CE01681H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H10 Br2 O'
_chemical_formula_sum            'C16 H10 Br2 O'
_chemical_formula_weight         378.06
_chemical_melting_point          398
_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           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3129(3)
_cell_length_b                   30.1720(12)
_cell_length_c                   7.2937(4)
_cell_measurement_reflns_used    10338
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.5640
_cell_measurement_theta_min      2.6770
_cell_volume                     1389.25(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  91.00   1.00   17.50    --   13.31  57.00  60.00  110
  2  ω    -23.00  97.00   1.00   17.50    --   13.31  77.00-180.00  120
  3  ω    -18.00  93.00   1.00   17.50    --   13.31  37.00 -30.00  111
  4  ω    -57.00  31.00   1.00   17.50    --  -14.40  94.00  37.00   88
  5  ω    -47.00  64.00   1.00   17.50    --  -14.40  57.00 -60.00  111
  6  ω    -50.00  70.00   1.00   17.50    --  -14.40  77.00-180.00  120
  7  ω    -76.00   1.00   1.00   17.50    --  -14.40 128.00-131.49   77
  8  ω    -79.00 105.00   1.00   17.50    --   13.31   0.00-180.00  184
  9  ω    -25.00  57.00   1.00   17.50    --   13.31 -99.00 150.00   82
 10  ω    -78.00 -32.00   1.00   17.50    --   13.31 178.00-120.00   46
 11  ω    -74.00   3.00   1.00   17.50    --  -14.40 125.00 -54.17   77
 12  ω    -55.00  37.00   1.00   17.50    --  -14.40  90.00-138.77   92
 13  ω    -57.00  31.00   1.00   17.50    --  -14.40  94.00 107.66   88
 14  ω    -79.00 105.00   1.00   17.50    --   13.31   0.00-120.00  184
 15  ω    -79.00 -27.00   1.00   17.50    --   13.31   0.00 -90.00   52
 16  ω    -79.00 105.00   1.00   17.50    --   13.31   0.00-150.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0104527000
_diffrn_orient_matrix_UB_12      0.0208175000
_diffrn_orient_matrix_UB_13      0.0442704000
_diffrn_orient_matrix_UB_21      -0.0732327000
_diffrn_orient_matrix_UB_22      -0.0068456000
_diffrn_orient_matrix_UB_23      0.0680907000
_diffrn_orient_matrix_UB_31      0.0845641000
_diffrn_orient_matrix_UB_32      -0.0085046000
_diffrn_orient_matrix_UB_33      0.0535052000
_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  0.0844
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            55420
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.471
_diffrn_reflns_theta_min         2.700
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.808
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method 'Crystallization from acetonitrille'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0420P)²+3.2277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1262
_reflns_number_total             1925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01681h2.cif
_cod_data_source_block           metafuranacn
_cod_depositor_comments
'Adding full bibliography for 7246100--7246102.cif.'
_cod_database_code               7246101
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br'
_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   0.622
_shelx_estimated_absorpt_t_min   0.250
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C6(H6), C2(H2), C5(H5)
;
_shelx_res_file
;
TITL metafuranacn_a.res in Pnma
    metafuranacn.res
    created by SHELXL-2018/3 at 11:57:22 on 27-Oct-2021
REM Old TITL
REM SHELXT solution in Pnma: R1 0.178, Rweak 0.124, Alpha 0.054
REM <I/s> 1.083 for 266 systematic absences, Orientation as input
REM Formula found by SHELXT: C16 O Br2
CELL 0.71073 6.3129 30.172 7.2937 90 90 90
ZERR 4 0.0003 0.0012 0.0004 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H Br O
UNIT 64 40 8 4

L.S. 4 0 0
PLAN  1
SIZE 0.09 0.23 0.33
TEMP 21.85
CONF
BOND
LIST 6
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\Metafuran%20ACN.hkl">
REM </olex2.extras>

WGHT    0.042000    3.227700
FVAR       0.26727
BR1   3    0.808477    0.460197    0.580432    11.00000    0.07694    0.04236 =
         0.09195    0.00028   -0.00809   -0.01343
O1    4    0.604689    0.250000    0.492839    10.50000    0.04141    0.03651 =
         0.04638    0.00000   -0.00311    0.00000
C3    1    0.627405    0.329873    0.504906    11.00000    0.04202    0.04112 =
         0.03740    0.00009    0.00241   -0.00213
C8    1    0.739082    0.367725    0.554865    11.00000    0.03661    0.04709 =
         0.04444    0.00247   -0.00088   -0.00349
AFIX  43
H8    2    0.873634    0.365462    0.605932    11.00000   -1.20000
AFIX   0
C1    1    0.726178    0.286678    0.527329    11.00000    0.04096    0.04220 =
         0.03903    0.00036   -0.00065   -0.00472
C4    1    0.423382    0.333986    0.433933    11.00000    0.03886    0.04955 =
         0.04451    0.00026    0.00025   -0.00282
AFIX  43
H4    2    0.346880    0.308901    0.400676    11.00000   -1.20000
AFIX   0
C7    1    0.647413    0.408597    0.527569    11.00000    0.04926    0.04224 =
         0.04461    0.00111    0.00315   -0.00726
C6    1    0.443584    0.413062    0.458550    11.00000    0.05838    0.04270 =
         0.05184    0.00248    0.00288    0.00675
AFIX  43
H6    2    0.382666    0.440895    0.443673    11.00000   -1.20000
AFIX   0
C2    1    0.921553    0.273413    0.581217    11.00000    0.04230    0.04938 =
         0.05451   -0.00039   -0.00745   -0.00508
AFIX  43
H2    2    1.034517    0.291708    0.612374    11.00000   -1.20000
AFIX   0
C5    1    0.335576    0.375738    0.413364    11.00000    0.04457    0.05843 =
         0.04871    0.00194   -0.00439    0.00537
AFIX  43
H5    2    0.198749    0.378279    0.367293    11.00000   -1.20000
AFIX   0
HKLF 4




REM  metafuranacn_a.res in Pnma
REM wR2 = 0.1354, GooF = S = 1.108, Restrained GooF = 1.108 for all data
REM R1 = 0.0578 for 1262 Fo > 4sig(Fo) and 0.1015 for all 1925 data
REM 88 parameters refined using 0 restraints

END

WGHT      0.0420      3.2278

REM Highest difference peak  0.640,  deepest hole -0.320,  1-sigma level  0.086
Q1    1   0.7346  0.4612  0.4798  11.00000  0.05    0.64
;
_shelx_res_checksum              75429
_olex2_date_sample_data_collection 2021-09-28
_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 2.245
_oxdiff_exptl_absorpt_empirical_full_min 0.755
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_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 0.80848(10) 0.46020(2) 0.58043(8) 0.0704(3) Uani 1 1 d . . . . .
O1 O 0.6047(6) 0.250000 0.4928(6) 0.0414(9) Uani 1 2 d S T P . .
C3 C 0.6274(7) 0.32987(14) 0.5049(6) 0.0402(9) Uani 1 1 d . . . . .
C8 C 0.7391(7) 0.36773(15) 0.5549(6) 0.0427(10) Uani 1 1 d . . . . .
H8 H 0.873634 0.365462 0.605932 0.051 Uiso 1 1 calc R U . . .
C1 C 0.7262(7) 0.28668(14) 0.5273(6) 0.0407(9) Uani 1 1 d . . . . .
C4 C 0.4234(7) 0.33399(15) 0.4339(6) 0.0443(10) Uani 1 1 d . . . . .
H4 H 0.346880 0.308901 0.400676 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6474(7) 0.40860(15) 0.5276(6) 0.0454(10) Uani 1 1 d . . . . .
C6 C 0.4436(8) 0.41306(15) 0.4585(6) 0.0510(11) Uani 1 1 d . . . . .
H6 H 0.382666 0.440895 0.443673 0.061 Uiso 1 1 calc R U . . .
C2 C 0.9216(7) 0.27341(15) 0.5812(6) 0.0487(11) Uani 1 1 d . . . . .
H2 H 1.034517 0.291708 0.612374 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3356(7) 0.37574(16) 0.4134(6) 0.0506(11) Uani 1 1 d . . . . .
H5 H 0.198749 0.378279 0.367293 0.061 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0769(4) 0.0424(3) 0.0920(5) 0.0003(3) -0.0081(3) -0.0134(2)
O1 0.041(2) 0.037(2) 0.046(2) 0.000 -0.003(2) 0.000
C3 0.042(2) 0.041(2) 0.037(2) 0.0001(18) 0.0024(18) -0.0021(18)
C8 0.037(2) 0.047(2) 0.044(2) 0.0025(19) -0.0009(18) -0.0035(18)
C1 0.041(2) 0.042(2) 0.039(2) 0.0004(18) -0.0006(18) -0.0047(18)
C4 0.039(2) 0.050(2) 0.045(2) 0.000(2) 0.0002(19) -0.0028(19)
C7 0.049(3) 0.042(2) 0.045(2) 0.0011(19) 0.003(2) -0.0073(19)
C6 0.058(3) 0.043(2) 0.052(3) 0.002(2) 0.003(2) 0.007(2)
C2 0.042(2) 0.049(2) 0.055(3) 0.000(2) -0.007(2) -0.005(2)
C5 0.045(3) 0.058(3) 0.049(3) 0.002(2) -0.004(2) 0.005(2)
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
_geom_angle_publ_flag
C1 O1 C1 107.8(4) . 7_565 ?
C8 C3 C1 119.3(4) . . ?
C8 C3 C4 119.5(4) . . ?
C4 C3 C1 121.2(4) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 C3 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
O1 C1 C3 117.6(4) . . ?
C2 C1 O1 108.9(4) . . ?
C2 C1 C3 133.5(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C8 C7 Br1 118.7(3) . . ?
C8 C7 C6 121.9(4) . . ?
C6 C7 Br1 119.4(3) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 C7 118.2(4) . . ?
C5 C6 H6 120.9 . . ?
C1 C2 C2 107.2(3) . 7_565 ?
C1 C2 H2 126.4 . . ?
C2 C2 H2 126.4 7_565 . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.899(4) . ?
O1 C1 1.370(5) . ?
O1 C1 1.370(5) 7_565 ?
C3 C8 1.391(6) . ?
C3 C1 1.454(6) . ?
C3 C4 1.394(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.377(6) . ?
C1 C2 1.355(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(6) . ?
C7 C6 1.388(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.357(7) . ?
C2 C2 1.413(9) 7_565 ?
C2 H2 0.9300 . ?
C5 H5 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
_geom_torsion_publ_flag
Br1 C7 C6 C5 176.8(3) . . . . ?
O1 C1 C2 C2 -0.3(4) . . . 7_565 ?
C3 C8 C7 Br1 -175.7(3) . . . . ?
C3 C8 C7 C6 2.6(6) . . . . ?
C3 C1 C2 C2 178.2(4) . . . 7_565 ?
C3 C4 C5 C6 0.8(7) . . . . ?
C8 C3 C1 O1 174.1(4) . . . . ?
C8 C3 C1 C2 -4.3(7) . . . . ?
C8 C3 C4 C5 0.4(6) . . . . ?
C8 C7 C6 C5 -1.6(7) . . . . ?
C1 O1 C1 C3 -178.3(2) 7_565 . . . ?
C1 O1 C1 C2 0.5(6) 7_565 . . . ?
C1 C3 C8 C7 177.8(4) . . . . ?
C1 C3 C4 C5 -179.5(4) . . . . ?
C4 C3 C8 C7 -2.0(6) . . . . ?
C4 C3 C1 O1 -6.1(6) . . . . ?
C4 C3 C1 C2 175.5(5) . . . . ?
C7 C6 C5 C4 -0.2(7) . . . . ?
