# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_metafuran
_database_code_depnum_ccdc_archive 'CCDC 2172053'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        2,5-bis(3-bromophenyl)furan
_chemical_formula_moiety         'C16 H10 Br2 O'
_chemical_formula_sum            'C16 H10 Br2 O'
_chemical_formula_weight         378.06
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOBr
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_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'

_cell_length_a                   8.278(3)
_cell_length_b                   13.527(4)
_cell_length_c                   12.503(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1400.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11746
_cell_measurement_temperature    295
_cell_measurement_theta_max      25.1180
_cell_measurement_theta_min      2.9830
_shelx_estimated_absorpt_T_max   0.624
_shelx_estimated_absorpt_T_min   0.185
_exptl_absorpt_coefficient_mu    5.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Crystallization from ethanol'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29237
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.436
_diffrn_reflns_theta_min         2.885
_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 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -35.00   1.00   20.00    --  -14.40-178.00 -90.00   72
  2  ω    -98.00  22.00   1.00   20.00    --  -14.40 -77.00-180.00  120
  3  ω    -25.00  57.00   1.00   20.00    --   13.31 -99.00-120.00   82
  4  ω    -65.00  46.00   1.00   20.00    --   13.31 -57.00  90.00  111
  5  ω    -18.00  93.00   1.00   20.00    --   13.31  37.00 150.00  111
  6  ω    -19.00  91.00   1.00   20.00    --   13.31  57.00  30.00  110
  7  ω    -78.00 -32.00   1.00   20.00    --   13.31 178.00  90.00   46
  8  ω   -105.00 -32.00   1.00   20.00    --  -14.40 178.00-150.00   73
  9  ω    -25.00  57.00   1.00   20.00    --   13.31 -99.00  60.00   82
 10  ω    -62.00   0.00   1.00   20.00    --  -14.40 105.00 104.00   62
;
_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      -0.0414942000
_diffrn_orient_matrix_UB_12      0.0352254000
_diffrn_orient_matrix_UB_13      -0.0317928000
_diffrn_orient_matrix_UB_21      0.0049075000
_diffrn_orient_matrix_UB_22      -0.0322481000
_diffrn_orient_matrix_UB_23      -0.0445956000
_diffrn_orient_matrix_UB_31      -0.0748382000
_diffrn_orient_matrix_UB_32      -0.0216465000
_diffrn_orient_matrix_UB_33      0.0147223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                2693
_reflns_number_total             3626
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.026
_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)+(0.0240P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C14(H14), C2(H2), C9(H9), C8(H8), C6(H6), C3(H3), C10(H10),
 C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br2 Br 0.20948(7) 0.89079(4) 0.71538(4) 0.06534(16) Uani 1 1 d . . . . .
Br1 Br 0.45165(7) 0.33842(3) 0.56883(5) 0.06641(16) Uani 1 1 d . . . . .
O1 O 0.6078(3) 0.7050(2) 0.4363(2) 0.0405(6) Uani 1 1 d . . . . .
C7 C 0.5658(5) 0.3966(3) 0.4515(4) 0.0472(11) Uani 1 1 d . . . . .
C16 C 0.4549(5) 0.8511(3) 0.5618(4) 0.0436(9) Uani 1 1 d . . . . .
H16 H 0.430064 0.785039 0.574124 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4124(6) 1.0236(3) 0.6024(4) 0.0557(12) Uani 1 1 d . . . . .
H14 H 0.358774 1.072565 0.640749 0.067 Uiso 1 1 calc R U . . .
C2 C 0.7771(6) 0.7104(3) 0.2984(4) 0.0496(11) Uani 1 1 d . . . . .
H2 H 0.842753 0.691594 0.241545 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7225(7) 0.3814(4) 0.2954(5) 0.0701(15) Uani 1 1 d . . . . .
H9 H 0.771414 0.342269 0.243541 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6369(7) 0.3366(4) 0.3771(4) 0.0597(13) Uani 1 1 d . . . . .
H8 H 0.628073 0.268200 0.381267 0.072 Uiso 1 1 calc R U . . .
C5 C 0.6648(5) 0.5424(3) 0.3655(4) 0.0414(10) Uani 1 1 d . . . . .
C6 C 0.5754(5) 0.4992(3) 0.4475(3) 0.0411(9) Uani 1 1 d . . . . .
H6 H 0.523426 0.538001 0.498319 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3760(6) 0.9247(3) 0.6184(4) 0.0470(10) Uani 1 1 d . . . . .
C3 C 0.7528(6) 0.8069(4) 0.3352(4) 0.0492(11) Uani 1 1 d . . . . .
H3 H 0.799537 0.863890 0.307269 0.059 Uiso 1 1 calc R U . . .
C11 C 0.5714(5) 0.8764(3) 0.4864(4) 0.0421(10) Uani 1 1 d . . . . .
C1 C 0.6876(5) 0.6491(3) 0.3605(4) 0.0428(10) Uani 1 1 d . . . . .
C10 C 0.7371(6) 0.4826(4) 0.2892(4) 0.0585(13) Uani 1 1 d . . . . .
H10 H 0.795596 0.510986 0.233555 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5301(6) 1.0482(4) 0.5284(4) 0.0615(14) Uani 1 1 d . . . . .
H13 H 0.555865 1.114286 0.516998 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6083(6) 0.9767(3) 0.4722(4) 0.0555(12) Uani 1 1 d . . . . .
H12 H 0.687845 0.994696 0.423359 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6484(5) 0.8023(3) 0.4193(3) 0.0414(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br2 C15 1.893(5) . ?
Br1 C7 1.914(5) . ?
O1 C1 1.381(5) . ?
O1 C4 1.375(5) . ?
C7 C8 1.368(7) . ?
C7 C6 1.391(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(6) . ?
C16 C11 1.391(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(7) . ?
C14 C13 1.384(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(7) . ?
C2 C1 1.356(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(8) . ?
C9 C10 1.376(7) . ?
C8 H8 0.9300 . ?
C5 C6 1.393(6) . ?
C5 C1 1.456(6) . ?
C5 C10 1.387(6) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.363(6) . ?
C11 C12 1.403(6) . ?
C11 C4 1.454(6) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.360(7) . ?
C12 H12 0.9300 . ?

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
C4 O1 C1 107.5(3) . . ?
C8 C7 Br1 119.3(4) . . ?
C8 C7 C6 122.9(4) . . ?
C6 C7 Br1 117.8(3) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C11 119.8(4) . . ?
C11 C16 H16 120.1 . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(4) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
C1 C2 C3 107.7(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C10 C9 C8 121.5(5) . . ?
C7 C8 C9 117.6(5) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C6 C5 C1 121.1(4) . . ?
C10 C5 C6 119.4(4) . . ?
C10 C5 C1 119.5(4) . . ?
C7 C6 C5 118.4(4) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C16 C15 Br2 119.8(3) . . ?
C16 C15 C14 121.2(4) . . ?
C14 C15 Br2 119.0(4) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 C2 107.6(4) . . ?
C4 C3 H3 126.2 . . ?
C16 C11 C12 118.3(4) . . ?
C16 C11 C4 121.7(4) . . ?
C12 C11 C4 119.9(4) . . ?
O1 C1 C5 116.8(4) . . ?
C2 C1 O1 108.6(4) . . ?
C2 C1 C5 134.5(4) . . ?
C9 C10 C5 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.7 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.4 . . ?
O1 C4 C11 117.6(4) . . ?
C3 C4 O1 108.6(4) . . ?
C3 C4 C11 133.8(4) . . ?

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 C8 C9 -178.0(4) . . . . ?
Br1 C7 C6 C5 176.9(3) . . . . ?
C16 C11 C12 C13 -1.6(7) . . . . ?
C16 C11 C4 O1 -3.0(6) . . . . ?
C16 C11 C4 C3 173.4(5) . . . . ?
C14 C13 C12 C11 0.7(7) . . . . ?
C2 C3 C4 O1 0.4(5) . . . . ?
C2 C3 C4 C11 -176.3(4) . . . . ?
C8 C7 C6 C5 -1.6(7) . . . . ?
C8 C9 C10 C5 -0.2(9) . . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C6 C5 C1 O1 -4.2(6) . . . . ?
C6 C5 C1 C2 173.0(5) . . . . ?
C6 C5 C10 C9 -1.0(8) . . . . ?
C15 C16 C11 C12 1.7(6) . . . . ?
C15 C16 C11 C4 -175.2(4) . . . . ?
C15 C14 C13 C12 0.1(7) . . . . ?
C3 C2 C1 O1 -0.3(5) . . . . ?
C3 C2 C1 C5 -177.7(5) . . . . ?
C11 C16 C15 Br2 176.6(3) . . . . ?
C11 C16 C15 C14 -0.9(7) . . . . ?
C1 O1 C4 C3 -0.6(4) . . . . ?
C1 O1 C4 C11 176.7(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C5 C6 C7 -176.3(4) . . . . ?
C1 C5 C10 C9 177.2(5) . . . . ?
C10 C9 C8 C7 0.5(9) . . . . ?
C10 C5 C6 C7 1.8(6) . . . . ?
C10 C5 C1 O1 177.7(4) . . . . ?
C10 C5 C1 C2 -5.1(7) . . . . ?
C13 C14 C15 Br2 -177.6(3) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C12 C11 C4 O1 -179.9(4) . . . . ?
C12 C11 C4 C3 -3.4(7) . . . . ?
C4 O1 C1 C2 0.6(4) . . . . ?
C4 O1 C1 C5 178.5(3) . . . . ?
C4 C11 C12 C13 175.3(4) . . . . ?

_olex2_date_sample_data_collection 2021-07-27
_olex2_exptl_crystal_mounting_method 'Crystal mounted on nail polish'
_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 2.833
_oxdiff_exptl_absorpt_empirical_full_min 0.683
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_metafuranacn
_database_code_depnum_ccdc_archive 'CCDC 2172056'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            MBFP
_chemical_name_systematic        2,5-bis(3-bromophenyl)furan
_chemical_formula_moiety         'C16 H10 Br2 O'
_chemical_formula_sum            'C16 H10 Br2 O'
_chemical_formula_weight         378.06
_chemical_melting_point          398
_chemical_oxdiff_formula         'C H O Br'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
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'

_cell_length_a                   6.3129(3)
_cell_length_b                   30.1720(12)
_cell_length_c                   7.2937(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1389.25(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10338
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.5640
_cell_measurement_theta_min      2.6770
_shelx_estimated_absorpt_T_max   0.622
_shelx_estimated_absorpt_T_min   0.250
_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_absorpt_special_details   ?
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1262
_reflns_number_total             1925
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.108
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
_chemical_properties_physical    'Metastable polymorph'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_metaruranaco_h2o
_database_code_depnum_ccdc_archive 'CCDC 2231826'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2022-12-20 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_audit_creation_date             2022-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            ?
_chemical_name_systematic        2,5-bis(3-bromophenyl)furan
_chemical_formula_moiety         'C16 H10 Br2 O'
_chemical_formula_sum            'C16 H10 Br2 O'
_chemical_formula_weight         378.06
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.1264(6)
_cell_length_b                   10.7891(16)
_cell_length_c                   31.194(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1388.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.5670
_cell_measurement_theta_min      3.7440
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.106
_exptl_absorpt_coefficient_mu    5.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52817
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Crystalization from the misxture 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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1968
_diffrn_reflns_av_unetI/netI     0.2106
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            30520
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.525
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  97.00   1.00   30.00    --   13.31  77.00 -60.00  120
  2  ω    -23.00  97.00   1.00   30.00    --   13.31  77.00  90.00  120
  3  ω    -51.00  69.00   1.00   30.00    --  -14.56  77.00-180.00  120
  4  ω     32.00 104.00   1.00   30.00    --   13.31-178.00   0.00   72
  5  ω    -65.00  46.00   1.00   30.00    --   13.31 -57.00   0.00  111
  6  ω     35.00 106.00   1.00   30.00    --   13.31 178.00-150.00   71
  7  ω    -89.00 -11.00   1.00   30.00    --  -14.56 148.00-152.01   78
  8  ω    -94.00  17.00   1.00   30.00    --  -14.56 -37.00 150.00  111
  9  ω    -25.00  29.00   1.00   30.00    --  -14.56 -99.00 150.00   54
 10  ω    -68.00 -41.00   1.00   30.00    --  -14.56 115.00   6.00   27
;
_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      0.0727450000
_diffrn_orient_matrix_UB_12      0.0314461000
_diffrn_orient_matrix_UB_13      -0.0175054000
_diffrn_orient_matrix_UB_21      0.0512901000
_diffrn_orient_matrix_UB_22      0.0478683000
_diffrn_orient_matrix_UB_23      0.0140084000
_diffrn_orient_matrix_UB_31      0.1470954000
_diffrn_orient_matrix_UB_32      -0.0322506000
_diffrn_orient_matrix_UB_33      0.0037733000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                1451
_reflns_number_total             3598
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.5 (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2650
_refine_ls_R_factor_gt           0.0966
_refine_ls_restrained_S_all      1.006
_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)+(0.0526P)²+1.8739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C8(H8), C16(H16), C3(H3), C14(H14), C10(H10), C7(H7),
 C15(H15), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br2 Br 0.5966(5) 0.57983(18) 0.64926(5) 0.0814(6) Uani 1 1 d . . . . .
Br1 Br 0.4668(5) 0.6522(2) 0.24487(6) 0.0947(7) Uani 1 1 d . . . . .
O1 O 0.381(2) 0.4858(8) 0.4449(3) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.512(3) 0.5457(11) 0.4803(4) 0.040(3) Uiso 1 1 d . . . . .
C13 C 0.461(3) 0.4952(14) 0.5978(4) 0.054(4) Uani 1 1 d . . . . .
C6 C 0.188(3) 0.4061(12) 0.3625(4) 0.044(4) Uani 1 1 d . . . . .
H6 H 0.130107 0.358040 0.386070 0.053 Uiso 1 1 calc R U . . .
C12 C 0.535(3) 0.5467(13) 0.5587(4) 0.055(4) Uani 1 1 d . . . . .
H12 H 0.652203 0.620098 0.557339 0.066 Uiso 1 1 calc R U . . .
C8 C 0.173(3) 0.4447(13) 0.2865(5) 0.059(4) Uani 1 1 d . . . . .
H8 H 0.102451 0.421496 0.259326 0.071 Uiso 1 1 calc R U . . .
C11 C 0.435(3) 0.4895(11) 0.5215(4) 0.044(3) Uani 1 1 d . . . . .
C1 C 0.474(3) 0.5570(11) 0.4099(4) 0.044(3) Uani 1 1 d . . . . .
C16 C 0.255(3) 0.3801(15) 0.5248(5) 0.063(5) Uani 1 1 d . . . . .
H16 H 0.184014 0.340568 0.500013 0.076 Uiso 1 1 calc R U . . .
C3 C 0.677(3) 0.6402(13) 0.4679(4) 0.047(4) Uani 1 1 d . . . . .
H3 H 0.794376 0.691865 0.486105 0.057 Uiso 1 1 calc R U . . .
C5 C 0.368(3) 0.5156(12) 0.3680(4) 0.048(4) Uani 1 1 d . . . . .
C9 C 0.350(4) 0.5509(14) 0.2925(4) 0.059(4) Uani 1 1 d . . . . .
C14 C 0.280(4) 0.3885(14) 0.6015(6) 0.067(5) Uani 1 1 d . . . . .
H14 H 0.225134 0.357036 0.628287 0.080 Uiso 1 1 calc R U . . .
C10 C 0.447(3) 0.5864(13) 0.3324(5) 0.054(4) Uani 1 1 d . . . . .
H10 H 0.566987 0.658667 0.335784 0.065 Uiso 1 1 calc R U . . .
C7 C 0.102(4) 0.3720(14) 0.3228(5) 0.065(4) Uani 1 1 d . . . . .
H7 H -0.007853 0.297603 0.319028 0.078 Uiso 1 1 calc R U . . .
C15 C 0.181(4) 0.3294(14) 0.5646(6) 0.065(5) Uani 1 1 d . . . . .
H15 H 0.064722 0.255667 0.566328 0.078 Uiso 1 1 calc R U . . .
C2 C 0.657(3) 0.6547(14) 0.4239(5) 0.062(4) Uani 1 1 d . . . . .
H2 H 0.748860 0.717382 0.407422 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br2 C13 1.930(13) . ?
Br1 C9 1.907(14) . ?
O1 C4 1.390(14) . ?
O1 C1 1.390(13) . ?
C4 C11 1.454(16) . ?
C4 C3 1.286(16) . ?
C13 C12 1.375(17) . ?
C13 C14 1.378(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.406(17) . ?
C6 C7 1.342(17) . ?
C12 H12 0.9300 . ?
C12 C11 1.378(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(19) . ?
C8 C7 1.408(19) . ?
C11 C16 1.398(19) . ?
C1 C5 1.448(17) . ?
C1 C2 1.370(17) . ?
C16 H16 0.9300 . ?
C16 C15 1.39(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.384(18) . ?
C5 C10 1.387(17) . ?
C9 C10 1.362(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(19) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?

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 C4 105.0(10) . . ?
O1 C4 C11 114.9(11) . . ?
C3 C4 O1 109.7(11) . . ?
C3 C4 C11 135.4(13) . . ?
C12 C13 Br2 118.9(12) . . ?
C12 C13 C14 122.1(14) . . ?
C14 C13 Br2 118.9(12) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C7 C6 C5 118.8(13) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.1(14) . . ?
C11 C12 H12 120.0 . . ?
C9 C8 H8 121.1 . . ?
C9 C8 C7 117.7(14) . . ?
C7 C8 H8 121.1 . . ?
C12 C11 C4 119.4(13) . . ?
C12 C11 C16 118.3(13) . . ?
C16 C11 C4 122.3(13) . . ?
O1 C1 C5 117.1(12) . . ?
C2 C1 O1 109.1(11) . . ?
C2 C1 C5 133.8(13) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.0(14) . . ?
C15 C16 H16 119.5 . . ?
C4 C3 H3 124.6 . . ?
C4 C3 C2 110.9(13) . . ?
C2 C3 H3 124.6 . . ?
C6 C5 C1 121.9(12) . . ?
C10 C5 C6 119.3(12) . . ?
C10 C5 C1 118.8(12) . . ?
C8 C9 Br1 120.4(12) . . ?
C10 C9 Br1 118.4(13) . . ?
C10 C9 C8 121.1(14) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(14) . . ?
C15 C14 H14 120.7 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.5(13) . . ?
C9 C10 H10 119.7 . . ?
C6 C7 C8 122.4(14) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 119.9(15) . . ?
C14 C15 H15 120.0 . . ?
C1 C2 C3 105.2(13) . . ?
C1 C2 H2 127.4 . . ?
C3 C2 H2 127.4 . . ?

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
Br2 C13 C12 C11 -178.6(10) . . . . ?
Br2 C13 C14 C15 179.4(11) . . . . ?
Br1 C9 C10 C5 -179.9(10) . . . . ?
O1 C4 C11 C12 -175.5(11) . . . . ?
O1 C4 C11 C16 3.1(17) . . . . ?
O1 C4 C3 C2 2.8(15) . . . . ?
O1 C1 C5 C6 -2.3(17) . . . . ?
O1 C1 C5 C10 177.8(11) . . . . ?
O1 C1 C2 C3 1.0(14) . . . . ?
C4 O1 C1 C5 -179.8(10) . . . . ?
C4 O1 C1 C2 0.6(13) . . . . ?
C4 C11 C16 C15 -179.2(13) . . . . ?
C4 C3 C2 C1 -2.4(15) . . . . ?
C13 C12 C11 C4 179.5(12) . . . . ?
C13 C12 C11 C16 0.7(19) . . . . ?
C13 C14 C15 C16 -2(2) . . . . ?
C6 C5 C10 C9 0(2) . . . . ?
C12 C13 C14 C15 3(2) . . . . ?
C12 C11 C16 C15 -0.5(19) . . . . ?
C8 C9 C10 C5 0(2) . . . . ?
C11 C4 C3 C2 -177.1(14) . . . . ?
C11 C16 C15 C14 1(2) . . . . ?
C1 O1 C4 C11 177.8(10) . . . . ?
C1 O1 C4 C3 -2.1(13) . . . . ?
C1 C5 C10 C9 -179.6(12) . . . . ?
C3 C4 C11 C12 4(2) . . . . ?
C3 C4 C11 C16 -177.0(14) . . . . ?
C5 C6 C7 C8 -3(2) . . . . ?
C5 C1 C2 C3 -178.5(13) . . . . ?
C9 C8 C7 C6 3(2) . . . . ?
C14 C13 C12 C11 -2(2) . . . . ?
C7 C6 C5 C1 -178.9(13) . . . . ?
C7 C6 C5 C10 1.0(19) . . . . ?
C7 C8 C9 Br1 178.2(11) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C2 C1 C5 C6 177.1(14) . . . . ?
C2 C1 C5 C10 -3(2) . . . . ?

_olex2_date_sample_data_collection 2021-09-30
_olex2_exptl_crystal_mounting_method 'Crystal mount on polish nail'
_olex2_submission_original_sample_id 'Gamma MPBG'
_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 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.668
