#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005185.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_2005185
loop_
_publ_author_name
'Banwell, M. G.'
'Forman, G. S.'
'Hockless, D. C. R.'
_publ_contact_author
;
Dr David C. R. Hockless
Research School of Chemistry
Institute of Advanced Studies
Australian National University
Canberra
ACT 0200
Australia
;
_publ_section_title
(3a<i>R</i>,3b<i>S</i>,4a<i>R</i>,4b<i>R</i>,5a<i>R</i>,5b<i>S</i>)-4,4,8,8-Tetrabromo-2,2-dimethylperhydrodicyclopropa[<i>e</i>,<i>g</i>][1,3]benzodioxole-3b-carbonitrile
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1804
_journal_page_last               1806
_journal_paper_doi               10.1107/S0108270195015319
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C12 H11 Br4 N O2 '
_chemical_formula_sum            'C12 H11 Br4 N O2'
_chemical_formula_weight         520.84
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 106.540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3220(10)
_cell_length_b                   13.4760(10)
_cell_length_c                   9.115(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    213.0(10)
_cell_measurement_theta_max      50.0
_cell_measurement_theta_min      48.9
_cell_volume                     744.4(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution
'SIR92 (Altomare et al., 1994); DIRDIF (Beurskens et al., 1992)'
_diffrn_ambient_temperature      213.0(10)
_diffrn_measurement_device       AFC6R
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1283
_diffrn_reflns_theta_max         60.05
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    13.348
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_type
'empirical, based on azimuthal (\y) scans (North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details   '\y scan'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.323
_exptl_crystal_description       irregular
_exptl_crystal_F_000             492.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.51
_refine_ls_extinction_coef       '1.5(3) x 10^-^^6^'
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   2.798
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1134
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0272
_refine_ls_shift/esd_max         0.0020
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.010F~o~^2^)^2^]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0325
_reflns_number_observed          1134
_reflns_number_total             1170
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ta1058.cif
_cod_data_source_block           GSF1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.010F~o~^2^)^2^]' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=4F~o~^2^/[\s^2^(F~o~^2^)+(0.010F~o~^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        744.5(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C12 H11 Br4 N O2 '
_cod_database_code               2005185
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,   -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br(4a) 0.0395(7) 0.0398(7) 0.0248(5) -0.0017(6) 0.0053(5) -0.0115(6)
Br(4b) 0.0295(6) 0.0458(7) 0.0212(5) -0.0034(5) 0.0101(4) 0.0053(5)
Br(5a) 0.0261(5) 0.0412(7) 0.0170(5) -0.0018(5) -0.0036(4) -0.0014(5)
Br(5b) 0.0258(6) 0.0595(9) 0.0187(5) -0.0063(6) 0.0069(4) 0.0029(6)
O(1) 0.027(4) 0.028(4) 0.024(4) -0.005(3) -0.008(3) 0.001(3)
O(3) 0.036(4) 0.026(4) 0.018(4) -0.003(3) 0.000(3) -0.001(3)
N(3b') 0.026(5) 0.052(7) 0.048(6) -0.013(5) 0.007(4) 0.006(5)
C(2) 0.040(7) 0.027(6) 0.015(5) -0.004(5) -0.004(5) 0.003(5)
C(2') 0.040(6) 0.037(7) 0.027(6) -0.006(6) 0.001(5) 0.003(5)
C(2'') 0.036(6) 0.038(7) 0.041(7) 0.008(6) -0.002(6) 0.003(6)
C(3a) 0.021(5) 0.038(6) 0.006(4) -0.008(5) -0.001(4) -0.005(5)
C(3b) 0.015(5) 0.034(6) 0.013(5) -0.001(5) 0.000(4) 0.003(4)
C(3b') 0.027(6) 0.033(6) 0.016(5) 0.002(5) 0.002(4) -0.001(5)
C(4a) 0.019(5) 0.024(6) 0.020(5) -0.001(4) 0.009(4) 0.000(4)
C(4b) 0.016(5) 0.032(6) 0.016(5) -0.001(5) 0.005(4) 0.008(5)
C(4) 0.020(5) 0.037(6) 0.018(5) -0.007(5) 0.004(4) 0.000(5)
C(5a) 0.014(5) 0.032(6) 0.023(6) -0.003(5) 0.001(4) 0.004(5)
C(5b) 0.026(6) 0.030(6) 0.018(6) -0.004(5) -0.002(5) -0.001(5)
C(5) 0.016(5) 0.039(7) 0.011(4) -0.001(5) 0.000(4) -0.008(5)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Br(4a) .0868(2) -0.0250 -0.17210(10) .0355(3) Uij
Br(4b) -0.1009(2) -0.24290(10) -0.18300(10) .0316(3) Uij
Br(5a) -0.3639(2) -0.2804 -0.86420(10) .0301(3) Uij
Br(5b) .1380(2) -0.21850(10) -0.73810(10) .0345(3) Uij
O(1) .1110(10) -0.4359(5) -0.3539(8) .029(2) Uij
O(3) .3570(10) -0.3295(6) -0.2106(7) .028(2) Uij
N(3b') .515(2) -.0495(8) -0.3610(10) .043(3) Uij
C(2) .309(2) -0.4334(8) -0.2260(10) .030(3) Uij
C(2') .254(2) -0.4688(9) -.0850(10) .036(3) Uij
C(2'') .491(2) -0.4889(9) -0.2650(10) .041(3) Uij
C(3a) .296(2) -0.2871(9) -0.3606(10) .023(3) Uij
C(3b) .218(2) -0.1796(8) -0.3550(10) .021(3) Uij
C(3b') .388(2) -0.1060(8) -0.3530(10) .026(3) Uij
C(4a) -.014(2) -0.1462(8) -0.4480(10) .021(3) Uij
C(4b) -0.1650(10) -0.2210(8) -0.5440(10) .021(3) Uij
C(4) .041(2) -0.1498(8) -0.2820(10) .025(3) Uij
C(5a) -.094(2) -0.3279(8) -0.5520(10) .024(3) Uij
C(5b) .135(2) -0.3640(8) -0.4610(10) .026(3) Uij
C(5) -0.1240(10) -0.2606(8) -0.6862(10) .023(3) Uij
H(2'a) .1659 -0.4204 -0.0542 .0437 Uij
H(2'b) .1752 -0.5295 -0.1064 .0437 Uij
H(2''a) .5160 -0.4612 -0.3544 .0496 Uij
H(2''b) .4513 -0.5567 -0.2825 .0496 Uij
H(2''c) .6226 -0.4839 -0.1823 .0496 Uij
H(2'c) .3865 -0.4787 -0.0049 .0437 Uij
H(3a) .4250 -0.2853 -0.3949 .0273 Uij
H(4b) -0.3166 -0.2125 -0.5493 .0256 Uij
H(4a) -0.0224 -0.0816 -0.4912 .0248 Uij
H(5b) .2045 -0.3940 -0.5296 .0316 Uij
H(5a) -0.2083 -0.3754 -0.5621 .0285 Uij
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol C, Tables 4.2.6.8 and 6.1.1.4)
;
H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol C, Tables 4.2.6.8 and 6.1.1.4)
;
Br -0.676 1.280
;
International Tables for Crystallography
(1992, Vol C, Tables 4.2.6.8 and 6.1.1.4)
;
N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol C, Tables 4.2.6.8 and 6.1.1.4)
;
O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 1
0 2 0
1 2 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) O(1) C(5b) 107.7(7) yes
C(2) O(3) C(3a) 107.9(8) yes
O(1) C(2) O(3) 102.1(8) yes
O(1) C(2) C(2') 109.0(9) yes
O(1) C(2) C(2'') 110.0(9) yes
O(3) C(2) C(2') 108.8(9) yes
O(3) C(2) C(2'') 110.8(9) yes
C(2') C(2) C(2'') 115.3(10) yes
O(3) C(3a) C(3b) 110.2(8) yes
O(3) C(3a) C(5b) 104.4(8) yes
C(3b) C(3a) C(5b) 119.0(8) yes
C(3a) C(3b) C(3b') 113.4(8) yes
C(3a) C(3b) C(4a) 121.5(8) yes
C(3a) C(3b) C(4) 123.6(8) yes
C(3b') C(3b) C(4a) 113.0(9) yes
C(3b') C(3b) C(4) 116.8(9) yes
C(4a) C(3b) C(4) 57.1(6) yes
N(3b') C(3b') C(3b) 175.0(10) yes
C(3b) C(4a) C(4b) 118.6(9) yes
C(3b) C(4a) C(4) 60.4(6) yes
C(4b) C(4a) C(4) 120.7(8) yes
C(4a) C(4b) C(5a) 121.4(8) yes
C(4a) C(4b) C(5) 120.5(8) yes
C(5a) C(4b) C(5) 59.3(7) yes
Br(4a) C(4) Br(4b) 110.4(5) yes
Br(4a) C(4) C(3b) 116.0(7) yes
Br(4a) C(4) C(4a) 117.7(8) yes
Br(4b) C(4) C(3b) 122.6(8) yes
Br(4b) C(4) C(4a) 120.5(7) yes
C(3b) C(4) C(4a) 62.4(6) yes
C(4b) C(5a) C(5b) 121.6(9) yes
C(4b) C(5a) C(5) 59.6(6) yes
C(5b) C(5a) C(5) 121.1(8) yes
O(1) C(5b) C(3a) 103.4(8) yes
O(1) C(5b) C(5a) 108.7(8) yes
C(3a) C(5b) C(5a) 118.0(9) yes
Br(5a) C(5) Br(5b) 111.4(4) yes
Br(5a) C(5) C(4b) 119.7(7) yes
Br(5a) C(5) C(5a) 119.9(7) yes
Br(5b) C(5) C(4b) 118.9(7) yes
Br(5b) C(5) C(5a) 117.6(6) yes
C(4b) C(5) C(5a) 61.1(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(4a) C(4) 1.930(10) yes
Br(4b) C(4) 1.910(10) yes
Br(5a) C(5) 1.900(9) yes
Br(5b) C(5) 1.930(9) yes
O(1) C(2) 1.450(10) yes
O(1) C(5b) 1.410(10) yes
O(3) C(2) 1.430(10) yes
O(3) C(3a) 1.430(10) yes
N(3b') C(3b') 1.130(10) yes
C(2) C(2') 1.500(10) yes
C(2) C(2'') 1.50(2) yes
C(3a) C(3b) 1.540(10) yes
C(3a) C(5b) 1.560(10) yes
C(3b) C(3b') 1.460(10) yes
C(3b) C(4a) 1.540(10) yes
C(3b) C(4) 1.510(10) yes
C(4a) C(4b) 1.490(10) yes
C(4a) C(4) 1.460(10) yes
C(4b) C(5a) 1.520(10) yes
C(4b) C(5) 1.500(10) yes
C(5a) C(5b) 1.530(10) yes
C(5a) C(5) 1.490(10) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055056