#------------------------------------------------------------------------------
#$Date: 2019-11-23 20:06:50 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234775 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/90/7059094.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_7059094
loop_
_publ_author_name
'Torubaev, Yury V.'
'Skabitskiy, Ivan V.'
'Pavlova, Alina V.'
'Pasynskii, Alexander A.'
_publ_section_title
;
 First structural evidence of a Se--Br--Br halogen-bonded molecular
 complex
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3606
_journal_paper_doi               10.1039/C6NJ04096A
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C8 H12 Br2 I2 Se'
_chemical_formula_sum            'C8 H12 Br2 I2 Se'
_chemical_formula_weight         600.76
_chemical_name_systematic
'2,6-dibromo-9-selenabicyclo[3.3.1]nonane diiodine'
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2016-12-27 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.587(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.503(3)
_cell_length_b                   10.107(4)
_cell_length_c                   18.967(7)
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.29
_cell_volume                     1418.2(10)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15260
_diffrn_reflns_theta_full        28.9984
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.598
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.2285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1693 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.3064.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.8134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1075.0188
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.5392
_refine_diff_density_min         -1.6889
_refine_diff_density_rms         0.1848
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             8.8915
_refine_ls_goodness_of_fit_ref   1.0100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     117
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0100
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0265P)²+2.4243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2914
_reflns_number_total             3749
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6nj04096a2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1418.2(9)
_cod_database_code               7059094
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
I1 I 0.14662(4) 0.66891(3) 0.477950(14) 0.04544(9) Uani 1.000000 .
I2 I -0.20342(5) 0.69351(4) 0.395312(17) 0.05866(11) Uani 1.000000 .
Br1 Br 0.92891(7) 0.96854(6) 0.60253(4) 0.07145(18) Uani 1.000000 .
Br2 Br 0.32789(7) 0.73009(7) 0.77702(3) 0.06808(17) Uani 1.000000 .
Se1 Se 0.50352(6) 0.63905(5) 0.55780(2) 0.04780(12) Uani 1.000000 .
C1 C 0.6056(6) 0.8202(4) 0.5647(2) 0.0424(9) Uani 1.000000 .
C2 C 0.4775(6) 0.9166(4) 0.5921(2) 0.0442(10) Uani 1.000000 .
C3 C 0.4264(6) 0.8890(4) 0.6655(2) 0.0461(10) Uani 1.000000 .
C4 C 0.3695(6) 0.7475(5) 0.6765(2) 0.0427(9) Uani 1.000000 .
C5 C 0.4975(6) 0.6390(4) 0.6615(2) 0.0435(10) Uani 1.000000 .
C6 C 0.6931(6) 0.6419(5) 0.6995(3) 0.0474(10) Uani 1.000000 .
C7 C 0.8076(6) 0.7631(5) 0.6859(2) 0.0465(10) Uani 1.000000 .
C8 C 0.7946(6) 0.8014(5) 0.6075(2) 0.0452(10) Uani 1.000000 .
H1 H 0.6188(6) 0.8482(4) 0.5164(2) 0.0509(11) Uiso 1.000000 R
H2a H 0.5316(6) 1.0039(4) 0.5935(2) 0.0530(12) Uiso 1.000000 R
H2b H 0.3669(6) 0.9197(4) 0.5574(2) 0.0530(12) Uiso 1.000000 R
H3a H 0.5291(6) 0.9103(4) 0.7020(2) 0.0553(12) Uiso 1.000000 R
H3b H 0.3282(6) 0.9476(4) 0.6722(2) 0.0553(12) Uiso 1.000000 R
H4 H 0.2535(6) 0.7326(5) 0.6451(2) 0.0513(11) Uiso 1.000000 R
H5 H 0.4454(6) 0.5545(4) 0.6731(2) 0.0522(11) Uiso 1.000000 R
H6a H 0.6930(6) 0.6359(5) 0.7505(3) 0.0569(13) Uiso 1.000000 R
H6b H 0.7530(6) 0.5634(5) 0.6856(3) 0.0569(13) Uiso 1.000000 R
H7a H 0.7699(6) 0.8381(5) 0.7118(2) 0.0558(12) Uiso 1.000000 R
H7b H 0.9331(6) 0.7450(5) 0.7054(2) 0.0558(12) Uiso 1.000000 R
H8 H 0.8552(6) 0.7325(5) 0.5838(2) 0.0542(12) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
Se1 I1 I2 178.156(16)
C1 Se1 I1 104.76(13)
C5 Se1 I1 110.61(13)
C5 Se1 C1 90.38(18)
C2 C1 Se1 110.8(3)
C8 C1 Se1 103.6(3)
C8 C1 C2 118.9(4)
C3 C2 C1 117.6(4)
C4 C3 C2 114.6(4)
C3 C4 Br2 107.9(3)
C5 C4 Br2 108.7(3)
C5 C4 C3 117.0(4)
C4 C5 Se1 107.8(3)
C6 C5 Se1 106.9(3)
C6 C5 C4 119.3(4)
C7 C6 C5 117.1(4)
C8 C7 C6 114.7(4)
C1 C8 Br1 107.7(3)
C7 C8 Br1 108.2(3)
C7 C8 C1 116.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 I2 2.8364(9)
I1 Se1 2.8644(10)
Br1 C8 1.977(5)
Br2 C4 1.991(4)
Se1 C1 1.980(4)
Se1 C5 1.976(5)
C1 C2 1.519(6)
C1 C8 1.524(6)
C2 C3 1.529(6)
C3 C4 1.518(6)
C4 C5 1.515(6)
C5 C6 1.524(6)
C6 C7 1.542(6)
C7 C8 1.525(6)
