#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018285.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_2018285
loop_
_publ_author_name
'Arumugam, Kuppuswamy'
'Clark, Daniel Seth'
'Mague, Joel T.'
'Donahue, James P.'
_publ_section_title
;
 The dithiolene ligand and tetrathiafulvalene precursor molecules
 4,5-bis(bromomethyl)-1,3-dithiol-2-one and
 4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-one
;
_journal_coeditor_code           FN3090
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o446
_journal_page_last               o449
_journal_paper_doi               10.1107/S0108270111040431
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H4 Br2 O S2'
_chemical_formula_moiety         'C5 H4 Br2 O S2'
_chemical_formula_sum            'C5 H4 Br2 O S2'
_chemical_formula_weight         304.02
_chemical_name_systematic
;
4,5-bis(bromomethyl)-1,3-dithiol-2-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.8360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9026(15)
_cell_length_b                   7.8804(8)
_cell_length_c                   7.4012(7)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.83
_cell_volume                     840.21(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008a)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008a)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7166
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    10.072
_exptl_absorpt_correction_T_max  0.4642
_exptl_absorpt_correction_T_min  0.3066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008b)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         1062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0223P)²+0.8485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0435
_reflns_number_gt                1005
_reflns_number_total             1062
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
ITL I in C2/c
CELL 0.71073  14.9026   7.8804   7.4012  90.000 104.836  90.000
ZERR    4.00   0.0015   0.0008   0.0007   0.000   0.001   0.000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C  H    O  Br S
UNIT 20  16  4  8  8
L.S. 6
FMAP 2
PLAN 5
BOND $H
OMIT -2 57.0
ACTA
SIZE 0.090 0.135 0.155
TEMP -173
WGHT    0.022300    0.848500
FVAR       0.11272
BR1   4    0.193908    0.368649    0.756184    11.00000    0.01267    0.01707 =
         0.02387    0.00491    0.00413   -0.00362
S1    5    0.094089   -0.030522    0.875979    11.00000    0.00988    0.00922 =
         0.01454    0.00139    0.00272    0.00188
O1    3    0.000000   -0.308368    0.750000    10.50000    0.02282    0.00830 =
         0.02823    0.00000    0.00540    0.00000
C1    1    0.000000   -0.154493    0.750000    10.50000    0.01547    0.01159 =
         0.01344    0.00000    0.00586    0.00000
C2    1    0.043028    0.166704    0.808141    11.00000    0.01159    0.00731 =
         0.01390    0.00015    0.00541    0.00039
C3    1    0.097663    0.320392    0.887890    11.00000    0.01196    0.01126 =
         0.01724   -0.00131    0.00375   -0.00193
AFIX  23
H3A   2    0.127173    0.301789    1.022271    11.00000   -1.20000
H3B   2    0.055504    0.419116    0.876601    11.00000   -1.20000
HKLF 4
REM  JPD211_0m in C2/c
REM R1 =  0.0164 for   1005 Fo > 4sig(Fo)  and  0.0180 for all   1062 data
REM     47 parameters refined using      0 restraints
END
WGHT      0.0226      0.8232
REM Highest difference peak  0.443,  deepest hole -0.440,  1-sigma level  0.120
Q1    1   0.1904  0.3516  0.6362  11.00000  0.05    0.44
Q2    1   0.1309  0.4248  1.0307  11.00000  0.05    0.42
Q3    1   0.0679  0.2437  0.8518  11.00000  0.05    0.41
Q4    1   0.0908 -0.0301  0.9764  11.00000  0.05    0.39
Q5    1   0.1375  0.3201  0.9758  11.00000  0.05    0.34
;
_cod_data_source_file            fn3090.cif
_cod_data_source_block           I
_cod_original_cell_volume        840.20(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018285
_cod_database_fobs_code          2018285
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.193908(12) 0.36865(2) 0.75618(3) 0.01797(8) Uani d . 1 1
S S1 0.09409(3) -0.03052(5) 0.87598(6) 0.01129(10) Uani d . 1 1
O O1 0.0000 -0.3084(2) 0.7500 0.0200(4) Uani d S 1 2
C C1 0.0000 -0.1545(3) 0.7500 0.0131(5) Uani d S 1 2
C C2 0.04303(12) 0.1667(2) 0.8081(2) 0.0105(3) Uani d . 1 1
C C3 0.09766(13) 0.3204(2) 0.8879(3) 0.0135(3) Uani d . 1 1
H H3A 0.1272 0.3018 1.0223 0.016 Uiso calc R 1 1
H H3B 0.0555 0.4191 0.8766 0.016 Uiso calc R 1 1
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
Br1 0.01267(11) 0.01707(11) 0.02387(12) -0.00362(7) 0.00413(8) 0.00491(7)
S1 0.0099(2) 0.00922(19) 0.0145(2) 0.00188(15) 0.00272(15) 0.00139(14)
O1 0.0228(10) 0.0083(8) 0.0282(11) 0.000 0.0054(8) 0.000
C1 0.0155(12) 0.0116(11) 0.0134(12) 0.000 0.0059(10) 0.000
C2 0.0116(8) 0.0073(7) 0.0139(8) 0.0004(6) 0.0054(7) 0.0002(6)
C3 0.0120(8) 0.0113(7) 0.0172(9) -0.0019(7) 0.0038(7) -0.0013(6)
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 S1 C1 . . 96.42(9)
O1 C1 S1 . . 123.58(7)
O1 C1 S1 . 2_556 123.58(7)
S1 C1 S1 . 2_556 112.85(13)
C2 C2 C3 2_556 . 125.80(10)
C2 C2 S1 2_556 . 117.15(6)
C3 C2 S1 . . 117.03(13)
C2 C3 Br1 . . 110.72(12)
C2 C3 H3A . . 109.5
Br1 C3 H3A . . 109.5
C2 C3 H3B . . 109.5
Br1 C3 H3B . . 109.5
H3A C3 H3B . . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C3 . 1.9667(18)
S1 C2 . 1.7467(17)
S1 C1 . 1.7664(14)
O1 C1 . 1.213(3)
C1 S1 2_556 1.7664(14)
C2 C2 2_556 1.349(4)
C2 C3 . 1.494(2)
C3 H3A . 0.9900
C3 H3B . 0.9900
