#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/70/2007023.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_2007023
loop_
_publ_author_name
'Honda, Kazumasa'
'Takasaki, Satoshi'
'Yamada, Jun-ichi'
'Nakatsuji, Shin-ichi'
'Anzai, Hiroyuki'
_publ_section_title
;
 Tetramethyltetrathiafulvalenium Bromide Benzonitrile Water Solvate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              261
_journal_page_last               264
_journal_paper_doi               10.1107/S0108270197013905
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac
'2(C10 H12 S4) + , 2 Br - , C7 H5 N , H2 O'
_chemical_formula_moiety         '2(C10 H12 S4), 2 Br, C7 H5 N, H2 O'
_chemical_formula_sum            'C27 H31 Br2 N O S8'
_chemical_formula_weight         801.84
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 90.53(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.424(4)
_cell_length_b                   9.689(4)
_cell_length_c                   14.470(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      13.1
_cell_volume                     3283.9(16)
_computing_cell_refinement       'AFC/MSC Diffractometer Control Software'
_computing_data_collection
'AFC/MSC Diffractometer Control Software (Rigaku Corporation, 1988)'
_computing_data_reduction
'TEXSAN PROCESS (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'TEXSAN FINISH (Molecular Structure Corporation, 1995)'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5174
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        -2.38
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   'analytical (de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      1.617
_exptl_crystal_density_method    'flotation in KI aqueous solution'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.000
_refine_ls_goodness_of_fit_obs   1.320
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1619
_refine_ls_R_factor_obs          .0530
_refine_ls_shift/esd_max         0.0004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0739
_refine_ls_wR_factor_obs         .0597
_reflns_number_observed          2552
_reflns_number_total             5060
_reflns_observed_criterion       >1.0sigma(I)
_cod_data_source_file            ln1035.cif
_cod_data_source_block           TM4C3rTh60_on_RASA-7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00063|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

2019-10-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         400.92
_cod_original_formula_moiety         '(C10 H12 S4), Br, (C7 H5 N)0.5, (H2 O)0.5'
_cod_original_formula_iupac
'(C10 H12 S4) + , Br - , 0.5C7 H5 N , 0.5H2 O'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        3284.0(10)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C13.50 H15.50 Br N0.50 O0.50 S4'
_cod_database_code               2007023
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,z
-x,-y,-z
-x,y,-z
1/2+x,1/2+y,z
1/2+x,1/2-y,z
1/2-x,1/2-y,-z
1/2-x,1/2+y,-z
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
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
Br1 .64624(4) .5000 .45850(7) .0667(3) Uani d . S 1.00
Br2 .14852(4) .0000 .04282(6) .0599(3) Uani d . S 1.00
S1 .55375(5) .85050(10) .37034(9) .0407(4) Uani d . . 1.00
S2 .41656(5) .85080(10) .39712(9) .0400(4) Uani d . . 1.00
S3 .54319(5) .14950(10) .87496(9) .0374(3) Uani d . . 1.00
S4 .40603(5) .15030(10) .89619(9) .0344(3) Uani d . . 1.00
O1 .2157(3) .0000 .2463(4) .081(2) Uani d . S 1.00
N1 .1933(3) .0000 .7319(6) .078(3) Uani d . S 1.00
C1 .5147(3) 1.0000 .3774(5) .036(2) Uani d . S 1.00
C2 .6194(2) .9319(5) .3543(3) .0380(10) Uani d . . 1.00
C3 .6693(2) .8355(7) .3418(4) .058(2) Uani d . . 1.00
C4 .4556(3) 1.0000 .3876(5) .035(2) Uani d . S 1.00
C5 .3504(2) .9302(5) .4049(3) .0370(10) Uani d . . 1.00
C6 .2990(2) .8390(6) .4083(4) .051(2) Uani d . . 1.00
C7 .5046(3) .0000 .8812(5) .033(2) Uani d . S 1.00
C8 .6096(2) .0703(5) .8618(3) .0350(10) Uani d . . 1.00
C9 .6598(2) .1635(6) .8533(4) .048(2) Uani d . . 1.00
C10 .4445(3) .0000 .8899(5) .033(2) Uani d . S 1.00
C11 .3397(2) .0691(5) .9022(3) .0340(10) Uani d . . 1.00
C12 .2874(2) .1576(5) .9048(4) .0450(10) Uani d . . 1.00
C13 .0589(4) .0000 .8296(6) .056(3) Uani d . S 1.00
C14 -.0007(4) .0000 .8375(7) .064(3) Uani d . S 1.00
C15 -.0328(4) .0000 .7579(9) .071(3) Uani d . S 1.00
C16 -.0080(4) .0000 .6707(7) .065(3) Uani d . S 1.00
C17 .0496(3) .0000 .6637(6) .049(2) Uani d . S 1.00
C18 .0831(3) .0000 .7439(6) .044(2) Uani d . S 1.00
C19 .1443(4) .0000 .7358(6) .057(3) Uani d . S 1.00
H1 .6682 .7927 .2779 .0583 Uiso calc . . 1.00
H2 .6751 .7688 .3870 .0583 Uiso calc . . 1.00
H3 .7007 .8743 .3412 .0583 Uiso calc . . 1.00
H4 .2787 .8274 .3405 .0760 Uiso calc . . 1.00
H5 .3086 .7626 .4371 .0760 Uiso calc . . 1.00
H6 .2696 .8798 .4548 .0760 Uiso calc . . 1.00
H7 .6628 .2007 .7963 .0722 Uiso calc . . 1.00
H8 .6926 .1149 .8701 .0722 Uiso calc . . 1.00
H9 .6581 .2517 .9024 .0722 Uiso calc . . 1.00
H10 .2669 .1608 .8481 .0671 Uiso calc . . 1.00
H11 .2955 .2554 .9103 .0671 Uiso calc . . 1.00
H12 .2625 .1455 .9561 .0671 Uiso calc . . 1.00
H13 .0832 .0000 .8922 .0671 Uiso calc . . 1.00
H14 -.0141 .0000 .9157 .0785 Uiso calc . . 1.00
H15 -.0816 .0000 .7519 .0861 Uiso calc . . 1.00
H16 -.0298 .0000 .6217 .0785 Uiso calc . . 1.00
H17 .0671 .0000 .6095 .0595 Uiso calc . . 1.00
H18 .1866 .0000 .3096 .1216 Uiso calc . . 1.00
H19 .1833 .0000 .1876 .1216 Uiso calc . . 1.00
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br -0.290 2.459
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 2
2 0 0
0 -2 0
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
C1 S1 C2 . . 95.6(2) yes
C4 S2 C5 . . 96.2(2) yes
C7 S3 C8 . . 96.1(2) yes
C10 S4 C11 . . 95.1(2) yes
H18 O1 H19 . . 101.4(5) no
S1 C1 S1 . 2_575 115.1(4) yes
S1 C1 C4 . . 122.4(2) yes
S1 C1 C4 2_575 . 122.4(2) no
S1 C2 C2 . 2_575 116.8(2) yes
S1 C2 C3 . . 114.9(4) no
C2 C2 C3 2_575 . 128.3(3) no
C2 C3 H1 . . 110.5(5) no
C2 C3 H2 . . 117.1(5) no
C2 C3 H3 . . 114.3(6) no
H1 C3 H2 . . 111.1(6) no
H1 C3 H3 . . 101.0(5) no
H2 C3 H3 . . 101.5(6) no
S2 C4 S2 . 2_575 114.7(4) yes
S2 C4 C1 . . 122.6(2) yes
S2 C4 C1 2_575 . 122.6(2) no
S2 C5 C5 . 2_575 116.3(2) yes
S2 C5 C6 . . 117.4(4) no
C5 C5 C6 2_575 . 126.3(3) no
C5 C6 H4 . . 112.0(4) no
C5 C6 H5 . . 108.2(5) no
C5 C6 H6 . . 109.5(5) no
H4 C6 H5 . . 116.4(6) no
H4 C6 H6 . . 109.5(5) no
H5 C6 H6 . . 100.4(5) no
S3 C7 S3 . 2_555 115.7(4) yes
S3 C7 C10 . . 122.1(2) yes
S3 C7 C10 2_555 . 122.1(2) no
S3 C8 C8 . 2_555 116.1(2) yes
S3 C8 C9 . . 116.6(4) no
C8 C8 C9 2_555 . 127.3(3) no
C8 C9 H7 . . 112.8(5) no
C8 C9 H8 . . 108.8(5) no
C8 C9 H9 . . 112.4(4) no
H7 C9 H8 . . 111.6(5) no
H7 C9 H9 . . 106.3(5) no
H8 C9 H9 . . 104.8(5) no
S4 C10 S4 . 2_555 116.2(4) yes
S4 C10 C7 . . 121.9(2) yes
S4 C10 C7 2_555 . 121.9(2) no
S4 C11 C11 . 2_555 116.8(2) yes
S4 C11 C12 . . 118.2(4) no
C11 C11 C12 2_555 . 125.0(3) no
C11 C12 H10 . . 113.9(5) no
C11 C12 H11 . . 113.8(4) no
C11 C12 H12 . . 117.0(5) no
H10 C12 H11 . . 97.9(5) no
H10 C12 H12 . . 111.6(5) no
H11 C12 H12 . . 100.1(5) no
C14 C13 C18 . . 119.7(9) no
C14 C13 H13 . . 117.1(9) no
C18 C13 H13 . . 123.2(8) no
C13 C14 C15 . . 118.1(9) no
C13 C14 H14 . . 110.7(9) no
C15 C14 H14 . . 131.2(10) no
C14 C15 C16 . . 122.0(8) no
C14 C15 H15 . . 127.0(10) no
C16 C15 H15 . . 110.0(10) no
C15 C16 C17 . . 119.5(9) no
C15 C16 H16 . . 119.0(10) no
C17 C16 H16 . . 121.0(10) no
C16 C17 C18 . . 119.4(8) no
C16 C17 H17 . . 122.4(9) no
C18 C17 H17 . . 118.2(8) no
C13 C18 C17 . . 121.2(8) no
C13 C18 C19 . . 119.7(8) no
C17 C18 C19 . . 119.1(8) no
N1 C19 C18 . . 178.2(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . . 1.716(4) yes
S1 C2 . . 1.746(5) yes
S2 C4 . . 1.717(4) yes
S2 C5 . . 1.736(4) yes
S3 C7 . . 1.711(3) yes
S3 C8 . . 1.746(4) yes
S4 C10 . . 1.715(4) yes
S4 C11 . . 1.744(4) yes
N1 C19 . . 1.150(10) no
C1 C4 . . 1.394(9) yes
C2 C2 . 2_575 1.321(10) yes
C2 C3 . . 1.507(7) no
C5 C5 . 2_575 1.352(10) yes
C5 C6 . . 1.494(6) no
C7 C10 . . 1.413(8) yes
C8 C8 . 2_555 1.362(10) yes
C8 C9 . . 1.488(6) no
C11 C11 . 2_555 1.339(10) yes
C11 C12 . . 1.495(6) no
C13 C14 . . 1.400(10) no
C13 C18 . . 1.370(10) no
C14 C15 . . 1.370(10) no
C15 C16 . . 1.390(10) no
C16 C17 . . 1.350(10) no
C17 C18 . . 1.390(10) no
C18 C19 . . 1.440(10) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
BR1 O1 3.488(6) 5_555 no
BR2 O1 3.326(7) . no
S1 S2 3.430(2) 4_656 no
S3 C13 3.479(2) 5_555 no
S3 S4 3.508(2) 4_657 no
S3 C14 3.588(4) 5_555 no
O1 C6 3.413(8) 1_545 no
O1 C6 3.413(8) 2_565 no
C1 C4 3.464(10) 3_676 no
C2 C5 3.549(7) 4_656 no
C7 C7 3.450(10) 3_657 no
C7 C10 3.510(10) 3_657 no
C9 C12 3.530(7) 6_555 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H18 BR1 5_445 1.14 2.36 3.488(6) 167
O1 H19 BR2 . 1.14 2.24 3.326(7) 159
