#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512737.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_4512737
loop_
_publ_author_name
'Koskinen, Laura'
'Jääskeläinen, Sirpa'
'Hirva, Pipsa'
'Haukka, Matti'
_publ_section_title
;
 Tunable Interaction Strength and Nature of the
 S···Br Halogen Bonds in [(Thione)Br2] Systems
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1160
_journal_paper_doi               10.1021/cg501482u
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C7 H6 Br N2 S, Br3'
_chemical_formula_sum            'C7 H6 Br4 N2 S'
_chemical_formula_weight         469.84
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                98.400(3)
_cell_angle_beta                 113.166(3)
_cell_angle_gamma                92.397(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2516(3)
_cell_length_b                   8.6933(2)
_cell_length_c                   8.9277(3)
_cell_measurement_reflns_used    9716
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.6900
_cell_measurement_theta_min      5.1670
_cell_volume                     578.98(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11790
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.986
_diffrn_reflns_theta_min         5.174
_diffrn_source                   micro-source
_exptl_absorpt_coefficient_mu    18.360
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8795
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;   
SADABS-2008/1 (Bruker, 2008)
Additional spherical absorption correction applied with mu*r =  0.0000
Lambda/2 correction factor = 0.0000
;
_exptl_crystal_colour            'orange yellow'
_exptl_crystal_density_diffrn    2.695
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0221
_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)+(0.0245P)²+0.9447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2408
_reflns_number_total             2427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501482u_si_003.cif
_cod_data_source_block           finalbr2
_cod_depositor_comments
'Adding full bibliography for 4512737--4512739.cif.'
_cod_original_cell_volume        578.98(3)
_cod_database_code               4512737
#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   0.133
_shelx_estimated_absorpt_t_max   0.356
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br -0.24984(3) 0.01462(3) -0.32121(3) 0.01782(8) Uani 1 1 d . .
S1 S -0.24434(8) 0.06939(8) -0.07265(8) 0.01647(14) Uani 1 1 d . .
N1 N 0.0304(3) 0.2736(3) -0.0585(3) 0.0142(4) Uani 1 1 d . .
N2 N -0.0027(3) 0.2866(3) 0.1734(3) 0.0156(4) Uani 1 1 d . .
C1 C -0.0657(3) 0.2152(3) 0.0145(3) 0.0151(5) Uani 1 1 d . .
C2 C 0.1620(3) 0.3866(3) 0.0562(3) 0.0141(5) Uani 1 1 d . .
C3 C 0.2934(3) 0.4808(3) 0.0403(4) 0.0170(5) Uani 1 1 d . .
H3 H 0.3069 0.4746 -0.0613 0.020 Uiso 1 1 calc R U
C4 C 0.4032(3) 0.5842(3) 0.1822(4) 0.0186(5) Uani 1 1 d . .
H4 H 0.4953 0.6505 0.1779 0.022 Uiso 1 1 calc R U
C5 C 0.3825(3) 0.5938(3) 0.3313(4) 0.0183(5) Uani 1 1 d . .
H5 H 0.4608 0.6664 0.4250 0.022 Uiso 1 1 calc R U
C6 C 0.2508(3) 0.5006(3) 0.3466(3) 0.0176(5) Uani 1 1 d . .
H6 H 0.2361 0.5078 0.4476 0.021 Uiso 1 1 calc R U
C7 C 0.1418(3) 0.3958(3) 0.2046(3) 0.0150(5) Uani 1 1 d . .
Br2 Br 0.25038(3) 0.04200(3) -0.31180(3) 0.01745(9) Uani 1 1 d . .
Br3 Br 0.09892(4) 0.28911(3) -0.40080(3) 0.01864(9) Uani 1 1 d . .
Br4 Br 0.38590(4) -0.20310(3) -0.23264(4) 0.02109(9) Uani 1 1 d . .
H1 H 0.014(4) 0.255(4) -0.152(5) 0.011(8) Uiso 1 1 d . .
H2 H -0.049(5) 0.269(4) 0.239(5) 0.018(8) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
_geom_angle_publ_flag
S1 Br1 Br2 176.16(2) 2_554 yes
C1 S1 Br1 99.08(9) . ?
C1 N1 C2 109.3(2) . ?
C1 N1 H1 127(2) . ?
C2 N1 H1 123(2) . ?
C1 N2 C7 108.8(2) . ?
C1 N2 H2 124(2) . ?
C7 N2 H2 127(2) . ?
N1 C1 N2 109.0(2) . ?
N1 C1 S1 127.9(2) . ?
N2 C1 S1 123.1(2) . ?
C7 C2 N1 106.7(2) . ?
C7 C2 C3 122.2(2) . ?
N1 C2 C3 131.1(3) . ?
C4 C3 C2 115.8(3) . ?
C4 C3 H3 122.1 . ?
C2 C3 H3 122.1 . ?
C3 C4 C5 122.0(2) . ?
C3 C4 H4 119.0 . ?
C5 C4 H4 119.0 . ?
C6 C5 C4 122.1(3) . ?
C6 C5 H5 118.9 . ?
C4 C5 H5 118.9 . ?
C5 C6 C7 115.8(3) . ?
C5 C6 H6 122.1 . ?
C7 C6 H6 122.1 . ?
C2 C7 C6 122.1(2) . ?
C2 C7 N2 106.1(2) . ?
C6 C7 N2 131.8(3) . ?
Br4 Br2 Br3 177.828(14) . yes
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 S1 2.1824(7) . yes
Br1 Br2 3.2395(4) 2_554 yes
S1 C1 1.743(3) . yes
N1 C1 1.335(3) . yes
N1 C2 1.391(3) . yes
N1 H1 0.78(4) . ?
N2 C1 1.343(4) . yes
N2 C7 1.403(3) . yes
N2 H2 0.84(4) . ?
C2 C7 1.390(4) . ?
C2 C3 1.395(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(4) . ?
C6 H6 0.9500 . ?
Br2 Br4 2.5115(4) . yes
Br2 Br3 2.5980(4) . yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 Br3 0.95 3.00 3.707(3) 132.7 . yes
C6 H6 Br3 0.95 2.92 3.644(3) 134.4 1_556 yes
N1 H1 Br1 0.78(4) 2.74(3) 3.110(2) 111(3) . yes
N1 H1 Br3 0.78(4) 2.63(4) 3.339(2) 152(3) . yes
N2 H2 Br3 0.84(4) 2.93(4) 3.552(2) 133(3) 1_556 yes
N2 H2 Br4 0.84(4) 2.80(4) 3.470(2) 139(3) 2 yes
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
C2 N1 C1 N2 0.4(3)
C2 N1 C1 S1 -179.18(19)
C7 N2 C1 N1 -0.3(3)
C7 N2 C1 S1 179.26(19)
Br1 S1 C1 N1 1.6(2)
Br1 S1 C1 N2 -177.9(2)
C1 N1 C2 C7 -0.3(3)
C1 N1 C2 C3 -179.5(3)
C7 C2 C3 C4 0.2(4)
N1 C2 C3 C4 179.2(3)
C2 C3 C4 C5 -0.4(4)
C3 C4 C5 C6 0.0(4)
C4 C5 C6 C7 0.6(4)
N1 C2 C7 C6 -178.8(2)
C3 C2 C7 C6 0.5(4)
N1 C2 C7 N2 0.1(3)
C3 C2 C7 N2 179.4(2)
C5 C6 C7 C2 -0.8(4)
C5 C6 C7 N2 -179.4(3)
C1 N2 C7 C2 0.1(3)
C1 N2 C7 C6 178.9(3)
