#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/49/1574954.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1574954
loop_
_publ_author_name
'Detert, Heiner'
'Schollmeyer, Dieter'
_publ_section_title
;
 rac-4,5-trans-Dibromo-9,9-dichloro-cis-bicyclo[6.1.0]nonane
;
_journal_coeditor_code           BT4172
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x250573
_journal_paper_doi               10.1107/S2414314625005735
_journal_volume                  10
_journal_year                    2025
_chemical_formula_iupac          'C9 H12 Br2 Cl2'
_chemical_formula_moiety         'C9 H12 Br2 Cl2'
_chemical_formula_sum            'C9 H12 Br2 Cl2'
_chemical_formula_weight         350.91
_chemical_name_common
rac-4,5-trans-Dibromo-9,9-dichloro-cis-bicyclo[6.1.0]nonane
_chemical_name_systematic
rac-4,5-trans-Dibromo-9,9-dichloro-cis-bicyclo[6.1.0]nonane
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 105.517(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2027(3)
_cell_length_b                   22.1157(10)
_cell_length_c                   7.5534(3)
_cell_measurement_reflns_used    9471
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.76
_cell_volume                     1159.35(9)
_computing_cell_refinement
;
X-Area Recipe 2.0.2 (Stoe & Cie, 2020)
;
_computing_data_collection
;
X-Area WinXpose 2.0.28 (Stoe & Cie, 2020)
;
_computing_data_reduction
;
X-Area Integrate 2.5.18.0 (Stoe & Cie, 2020)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6364
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.911
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'sealed X-ray tube, 12x0.4mm long-fine focus'
_exptl_absorpt_coefficient_mu    7.407
_exptl_absorpt_correction_T_max  0.3578
_exptl_absorpt_correction_T_min  0.0693
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-Red32 (Stoe & Cie, 2020) absorption correction by Gaussian
integration]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.395
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0404
_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)+(0.0367P)²+2.8083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2469
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4172.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574954
#BEGIN Tags that were not found in dictionaries:
_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_min   0.119
_shelx_estimated_absorpt_t_max   0.446
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.67566(14) 0.67134(4) 0.60825(12) 0.0288(2) Uani d 1 . .
Cl Cl2 0.83981(13) 0.55561(4) 0.55570(12) 0.02610(19) Uani d 1 . .
Br Br1 0.0626(5) 0.72992(15) 0.0378(5) 0.0261(4) Uani d 0.638(9) A 1
Br Br2 0.2483(2) 0.53409(6) -0.0565(4) 0.0289(4) Uani d 0.638(9) A 1
C C1 0.1135(9) 0.6031(4) 0.0199(9) 0.0243(14) Uani d 0.638(9) A 1
H H1 -0.023418 0.599338 -0.054723 0.029 Uiso calc 0.638(9) A 1
C C2 0.1880(9) 0.6610(3) -0.0491(8) 0.0232(13) Uani d 0.638(9) A 1
H H2 0.130604 0.660373 -0.185198 0.028 Uiso calc 0.638(9) A 1
Br Br1A 0.2998(9) 0.5459(2) -0.1082(6) 0.0393(12) Uani d 0.362(9) A 2
Br Br2A 0.0345(11) 0.7209(3) 0.0592(9) 0.0336(10) Uani d 0.362(9) A 2
C C1A 0.0875(14) 0.6337(7) 0.0252(13) 0.021(2) Uani d 0.362(9) A 2
H H1A -0.033261 0.617909 -0.061182 0.026 Uiso calc 0.362(9) A 2
C C2A 0.2366(16) 0.6317(6) -0.0823(13) 0.024(2) Uani d 0.362(9) A 2
H H2A 0.167411 0.645242 -0.209057 0.028 Uiso calc 0.362(9) A 2
C C3 0.4082(6) 0.67226(18) -0.0243(5) 0.0287(8) Uani d 1 . .
H H3A 0.457248 0.639468 -0.088844 0.034 Uiso calc 0.638(9) A 1
H H3B 0.422031 0.710584 -0.087348 0.034 Uiso calc 0.638(9) A 1
H H3C 0.360886 0.713840 -0.057962 0.034 Uiso calc 0.362(9) A 2
H H3D 0.492984 0.662025 -0.103791 0.034 Uiso calc 0.362(9) A 2
C C4 0.5379(5) 0.67580(16) 0.1709(5) 0.0242(7) Uani d 1 . .
H H4A 0.657883 0.697353 0.169044 0.029 Uiso calc 1 . .
H H4B 0.472136 0.699838 0.246652 0.029 Uiso calc 1 . .
C C5 0.5899(5) 0.61482(15) 0.2597(5) 0.0192(6) Uani d 1 . .
H H5 0.653803 0.586721 0.190526 0.023 Uiso calc 1 . .
C C6 0.4614(5) 0.58393(15) 0.3632(5) 0.0206(7) Uani d 1 . .
H H6 0.454627 0.538915 0.350552 0.025 Uiso calc 1 . .
C C7 0.2773(5) 0.61350(17) 0.3764(5) 0.0237(7) Uani d 1 . .
H H7A 0.295303 0.657907 0.382082 0.028 Uiso calc 1 . .
H H7B 0.248641 0.600487 0.491711 0.028 Uiso calc 1 . .
C C8 0.1061(5) 0.59791(18) 0.2141(5) 0.0266(7) Uani d 1 . .
H H8A 0.070570 0.555553 0.232062 0.032 Uiso calc 0.638(9) A 1
H H8B -0.002787 0.623390 0.226302 0.032 Uiso calc 0.638(9) A 1
H H8C -0.013285 0.604977 0.252293 0.032 Uiso calc 0.362(9) A 2
H H8D 0.112053 0.554131 0.188845 0.032 Uiso calc 0.362(9) A 2
C C9 0.6542(5) 0.60790(15) 0.4640(5) 0.0201(6) Uani d 1 . .
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'
Cl Cl 0.1484 0.1585 '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
1 -4 -2 0.3710
0 3 1 0.3150
0 -1 0 0.2140
0 2 -1 0.1260
1 0 0 0.0630
-1 0 0 0.0820
-1 -3 2 0.3890
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 C1 C2 . . 120.5(6) ?
C8 C1 Br2 . . 112.3(4) ?
C2 C1 Br2 . . 107.6(5) ?
C8 C1 H1 . . 105.0 ?
C2 C1 H1 . . 105.0 ?
Br2 C1 H1 . . 105.0 ?
C1 C2 C3 . . 121.8(5) ?
C1 C2 Br1 . . 107.4(5) ?
C3 C2 Br1 . . 112.1(4) ?
C1 C2 H2 . . 104.6 ?
C3 C2 H2 . . 104.6 ?
Br1 C2 H2 . . 104.6 ?
C2A C1A C8 . . 124.1(10) ?
C2A C1A Br2A . . 106.6(10) ?
C8 C1A Br2A . . 109.6(6) ?
C2A C1A H1A . . 105.0 ?
C8 C1A H1A . . 105.0 ?
Br2A C1A H1A . . 105.0 ?
C3 C2A C1A . . 118.5(10) ?
C3 C2A Br1A . . 114.3(7) ?
C1A C2A Br1A . . 107.3(10) ?
C3 C2A H2A . . 105.2 ?
C1A C2A H2A . . 105.2 ?
Br1A C2A H2A . . 105.2 ?
C2A C3 C4 . . 124.0(4) ?
C4 C3 C2 . . 117.6(3) ?
C4 C3 H3A . . 107.9 ?
C2 C3 H3A . . 107.9 ?
C4 C3 H3B . . 107.9 ?
C2 C3 H3B . . 107.9 ?
H3A C3 H3B . . 107.2 ?
C2A C3 H3C . . 106.3 ?
C4 C3 H3C . . 106.3 ?
C2A C3 H3D . . 106.3 ?
C4 C3 H3D . . 106.3 ?
H3C C3 H3D . . 106.4 ?
C5 C4 C3 . . 113.6(3) ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C9 C5 C4 . . 121.5(3) ?
C9 C5 C6 . . 59.2(2) ?
C4 C5 C6 . . 121.1(3) ?
C9 C5 H5 . . 114.7 ?
C4 C5 H5 . . 114.7 ?
C6 C5 H5 . . 114.7 ?
C9 C6 C7 . . 121.9(3) ?
C9 C6 C5 . . 59.4(2) ?
C7 C6 C5 . . 120.4(3) ?
C9 C6 H6 . . 114.7 ?
C7 C6 H6 . . 114.7 ?
C5 C6 H6 . . 114.7 ?
C6 C7 C8 . . 112.6(3) ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C1 C8 C7 . . 122.7(4) ?
C7 C8 C1A . . 117.4(5) ?
C1 C8 H8A . . 106.7 ?
C7 C8 H8A . . 106.7 ?
C1 C8 H8B . . 106.7 ?
C7 C8 H8B . . 106.7 ?
H8A C8 H8B . . 106.6 ?
C7 C8 H8C . . 108.0 ?
C1A C8 H8C . . 108.0 ?
C7 C8 H8D . . 108.0 ?
C1A C8 H8D . . 108.0 ?
H8C C8 H8D . . 107.2 ?
C6 C9 C5 . . 61.4(2) ?
C6 C9 Cl1 . . 121.0(3) ?
C5 C9 Cl1 . . 120.6(2) ?
C6 C9 Cl2 . . 118.2(2) ?
C5 C9 Cl2 . . 117.7(2) ?
Cl1 C9 Cl2 . . 110.36(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 . 1.758(3) ?
Cl2 C9 . 1.763(3) ?
Br1 C2 . 1.972(9) ?
Br2 C1 . 1.975(9) ?
C1 C8 . 1.487(7) ?
C1 C2 . 1.533(10) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.567(7) ?
C2 H2 . 1.0000 ?
Br1A C2A . 1.973(14) ?
Br2A C1A . 1.997(18) ?
C1A C2A . 1.510(17) ?
C1A C8 . 1.606(12) ?
C1A H1A . 1.0000 ?
C2A C3 . 1.495(12) ?
C2A H2A . 1.0000 ?
C3 C4 . 1.522(5) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C3 H3C . 0.9900 ?
C3 H3D . 0.9900 ?
C4 C5 . 1.508(5) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C9 . 1.495(5) ?
C5 C6 . 1.524(5) ?
C5 H5 . 1.0000 ?
C6 C9 . 1.491(5) ?
C6 C7 . 1.505(5) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.528(5) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8 H8C . 0.9900 ?
C8 H8D . 0.9900 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C1 C2 C3 . . . . 84.4(8) ?
Br2 C1 C2 C3 . . . . -46.0(7) ?
C8 C1 C2 Br1 . . . . -46.9(7) ?
Br2 C1 C2 Br1 . . . . -177.3(3) ?
C8 C1A C2A C3 . . . . -82.3(15) ?
Br2A C1A C2A C3 . . . . 46.3(10) ?
C8 C1A C2A Br1A . . . . 48.9(11) ?
Br2A C1A C2A Br1A . . . . 177.6(5) ?
C1A C2A C3 C4 . . . . 52.0(13) ?
Br1A C2A C3 C4 . . . . -76.0(7) ?
C1 C2 C3 C4 . . . . -62.2(7) ?
Br1 C2 C3 C4 . . . . 67.1(5) ?
C2A C3 C4 C5 . . . . 44.4(8) ?
C2 C3 C4 C5 . . . . 79.2(5) ?
C3 C4 C5 C9 . . . . -158.2(3) ?
C3 C4 C5 C6 . . . . -87.6(4) ?
C4 C5 C6 C9 . . . . -110.5(4) ?
C9 C5 C6 C7 . . . . 111.4(4) ?
C4 C5 C6 C7 . . . . 0.9(5) ?
C9 C6 C7 C8 . . . . 158.3(3) ?
C5 C6 C7 C8 . . . . 87.5(4) ?
C2 C1 C8 C7 . . . . -49.5(8) ?
Br2 C1 C8 C7 . . . . 78.9(5) ?
C6 C7 C8 C1 . . . . -49.5(6) ?
C6 C7 C8 C1A . . . . -79.0(7) ?
C2A C1A C8 C7 . . . . 60.9(13) ?
Br2A C1A C8 C7 . . . . -66.4(7) ?
C7 C6 C9 C5 . . . . -108.9(3) ?
C7 C6 C9 Cl1 . . . . 1.5(4) ?
C5 C6 C9 Cl1 . . . . 110.4(3) ?
C7 C6 C9 Cl2 . . . . 143.1(3) ?
C5 C6 C9 Cl2 . . . . -108.0(3) ?
C4 C5 C9 C6 . . . . 109.9(4) ?
C4 C5 C9 Cl1 . . . . -1.2(5) ?
C6 C5 C9 Cl1 . . . . -111.1(3) ?
C4 C5 C9 Cl2 . . . . -141.4(3) ?
C6 C5 C9 Cl2 . . . . 108.7(3) ?
