#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:08:44 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246252.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_7246252
loop_
_publ_author_name
'Stoesser, Julian'
'Engelage, Elric'
'Belmonte, Debora'
'Huber, Stefan M.'
_publ_section_title
;
 Just at the limit: binding studies with neutral brominated
 terphenyl-derived halogen bond donors
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1501
_journal_page_last               1506
_journal_paper_doi               10.1039/D2CE01629J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C18 Br4 F10'
_chemical_formula_weight         725.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.079(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3920(12)
_cell_length_b                   10.6012(12)
_cell_length_c                   14.1313(13)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.7
_cell_volume                     1968.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_molecular_graphics
;
 Diamond 4 - Crystal and Molecular Structure Visualization
  Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, 
  Kreuzherrenstr. 102, 53227 Bonn, Germany
  http://www.crystalimpact.com/diamond
 Mercury CSD 2.0 - New Features for the Visualization 
 and Investigation of Crystal Structures
  C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe,
  E. Pidcock, 
  L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, 
  J. Appl. Cryst., 41, 466-470, 2008
;
_computing_publication_material
'WinGX L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
 shelXT  G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr.,
 2008, 64, 112-122.
 shelXle C. B. Huebschle, G. M. Sheldrick and B. Dittrich J. Appl. Cryst.
  (2011). 44, 1281-1284
;
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.273
_exptl_absorpt_correction_T_max  0.504
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.449
_exptl_crystal_description       prism
_exptl_crystal_F_000             1352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Slow evaporation of pentane'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0308
_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)+(0.0329P)²+2.0204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1513
_reflns_number_total             1935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01629j3.cif
_cod_data_source_block           js-db-a01a
_cod_depositor_comments
'Adding full bibliography for 7246252--7246257.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7246252
_shelx_shelxl_version_number     2018/3
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.859
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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 0.62680(3) 0.74664(4) 0.51529(3) 0.04347(15) Uani 1 1 d . . . . .
F1 F 0.5141(2) 0.8848(3) 0.64665(16) 0.0579(7) Uani 1 1 d . . . . .
C1 C 0.4904(3) 0.8003(4) 0.4897(3) 0.0315(8) Uani 1 1 d . . . . .
Br2 Br 0.23885(3) 0.79968(5) 0.26629(3) 0.05557(17) Uani 1 1 d . . . . .
F2 F 0.3203(2) 0.9721(3) 0.61335(18) 0.0652(8) Uani 1 1 d . . . . .
C2 C 0.4539(3) 0.8643(4) 0.5610(3) 0.0396(10) Uani 1 1 d . . . . .
F3 F 0.1982(2) 0.9340(3) 0.4428(2) 0.0643(8) Uani 1 1 d . . . . .
C3 C 0.3553(4) 0.9090(4) 0.5442(3) 0.0454(11) Uani 1 1 d . . . . .
F4 F 0.500000 0.8959(3) 0.250000 0.0417(8) Uani 1 2 d S T P . .
C4 C 0.2931(3) 0.8890(4) 0.4571(3) 0.0439(10) Uani 1 1 d . . . . .
C5 C 0.3279(3) 0.8243(4) 0.3851(3) 0.0370(9) Uani 1 1 d . . . . .
F5 F 0.43560(17) 0.5129(2) 0.39209(16) 0.0474(6) Uani 1 1 d . . . . .
C6 C 0.4276(3) 0.7788(3) 0.4005(2) 0.0301(9) Uani 1 1 d . . . . .
F6 F 0.500000 0.3850(3) 0.250000 0.0490(9) Uani 1 2 d S T P . .
C7 C 0.4652(3) 0.7074(4) 0.3239(2) 0.0294(8) Uani 1 1 d . . . . .
C10 C 0.500000 0.5106(5) 0.250000 0.0332(12) Uani 1 2 d S T P . .
C9 C 0.4670(3) 0.5772(4) 0.3221(3) 0.0342(9) Uani 1 1 d . . . . .
C8 C 0.500000 0.7697(5) 0.250000 0.0298(12) Uani 1 2 d S T P . .
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'
F F 0.0171 0.0103 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 11 23 0.0593
21 0 10 0.0736
0 11 -23 0.0576
-21 0 -10 0.0857
-13 -17 3 0.0478
0 0 -4 0.0796
-1 0 3 0.0759
3 0 -1 0.0871
1 1 2 0.0497
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
C2 C1 C6 120.3(4) . . ?
C2 C1 Br1 118.4(3) . . ?
C6 C1 Br1 121.3(3) . . ?
F1 C2 C3 119.4(4) . . ?
F1 C2 C1 120.3(4) . . ?
C3 C2 C1 120.3(4) . . ?
F2 C3 C4 119.8(4) . . ?
F2 C3 C2 120.2(4) . . ?
C4 C3 C2 120.1(4) . . ?
F3 C4 C3 118.7(4) . . ?
F3 C4 C5 120.8(4) . . ?
C3 C4 C5 120.5(4) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 Br2 118.7(3) . . ?
C6 C5 Br2 120.9(3) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 120.8(3) . . ?
C5 C6 C7 120.7(3) . . ?
C9 C7 C8 116.8(3) . . ?
C9 C7 C6 122.2(3) . . ?
C8 C7 C6 121.0(4) . . ?
F6 C10 C9 120.8(3) . . ?
F6 C10 C9 120.8(3) . 2_655 ?
C9 C10 C9 118.4(5) . 2_655 ?
F5 C9 C10 118.4(4) . . ?
F5 C9 C7 119.2(3) . . ?
C10 C9 C7 122.4(3) . . ?
F4 C8 C7 118.4(2) . 2_655 ?
F4 C8 C7 118.4(2) . . ?
C7 C8 C7 123.3(5) 2_655 . ?
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 C1 1.881(4) . ?
F1 C2 1.337(4) . ?
C1 C2 1.380(5) . ?
C1 C6 1.393(5) . ?
Br2 C5 1.882(4) . ?
F2 C3 1.342(4) . ?
C2 C3 1.380(6) . ?
F3 C4 1.336(5) . ?
C3 C4 1.363(6) . ?
F4 C8 1.338(6) . ?
C4 C5 1.380(5) . ?
C5 C6 1.396(5) . ?
F5 C9 1.335(4) . ?
C6 C7 1.486(5) . ?
F6 C10 1.331(6) . ?
C7 C9 1.381(5) . ?
C7 C8 1.390(4) . ?
C10 C9 1.380(5) . ?
C10 C9 1.380(5) 2_655 ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0316 11.0100 22.9037 -0.6715 0.1142 -1.2049
20.9194 0.0052 10.0106 -1.0600 0.7965 -0.0445
0.0454 11.0034 -22.9279 1.2476 0.5951 0.0490
-20.9194 -0.0052 -10.0106 1.0600 -0.7965 0.0445
-13.0124 -17.0123 2.9785 -0.1723 -1.1373 0.6703
0.0009 -0.0601 -3.5626 0.1476 0.0355 0.1006
-0.6219 -0.4664 2.7654 -0.1090 -0.0707 -0.0579
2.7723 0.0004 -0.7030 -0.0555 0.1268 0.0496
0.6154 0.7464 1.8458 -0.0766 0.0311 -0.0830
