#------------------------------------------------------------------------------
#$Date: 2017-03-04 07:21:01 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/57/4125781.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_4125781
loop_
_publ_author_name
'Mailman, Aaron'
'Leitch, Alicea A.'
'Yong, Wenjun'
'Steven, Eden'
'Winter, Stephen M.'
'Claridge, Robert C. M.'
'Assoud, Abdeljalil'
'Tse, John S.'
'Desgreniers, Serge'
'Secco, Richard A.'
'Oakley, Richard T.'
_publ_section_title
;
 The Power of Packing: Metallization of an Organic Semiconductor.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2180
_journal_page_last               2183
_journal_paper_doi               10.1021/jacs.6b12814
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C6 N2 O2 S4'
_chemical_formula_sum            'C6 N2 O2 S4'
_chemical_formula_weight         260.32
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3278(15)
_cell_length_b                   7.8999(19)
_cell_length_c                   15.744(4)
_cell_measurement_reflns_used    361
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      1.5
_cell_volume                     787.0(3)
_computing_cell_refinement       'SMART, 'Bruker APEX II'
_computing_data_collection       'Bruker Kappa APEX II'
_computing_data_reduction        'SAINT, 'Bruker APEX II'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       'Omega scan'
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2408
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.985
_diffrn_reflns_theta_min         4.126
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  3
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.170
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_description       Plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0249P)²+2.1466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                935
_reflns_number_total             991
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12814_si_003.cif
_cod_data_source_block           c6n2o2s4_0m
_cod_database_code               4125781
_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   0.892
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
_atom_site_refinement_flags_occupancy
S1 S 1.0000 0.3751(3) 0.38733(15) 0.0277(6) Uani 1 2 d S T P
S2 S 1.0000 0.6310(3) 0.41933(12) 0.0264(6) Uani 1 2 d S T P
S3 S 1.0000 1.0122(3) 0.04029(17) 0.0309(6) Uani 1 2 d S T P
S4 S 1.0000 1.0983(3) 0.16566(14) 0.0239(5) Uani 1 2 d S T P
N1 N 1.0000 0.3974(10) 0.2858(5) 0.0253(16) Uani 1 2 d S T P
N2 N 1.0000 0.8090(10) 0.0579(5) 0.030(2) Uani 1 2 d S T P
O1 O 1.0000 0.4689(8) 0.1110(4) 0.0295(15) Uani 1 2 d S T P
O2 O 1.0000 0.9839(9) 0.3461(4) 0.0286(14) Uani 1 2 d S T P
C6 C 1.0000 0.5813(10) 0.1639(6) 0.0213(16) Uani 1 2 d S T P
C5 C 1.0000 0.7666(10) 0.1393(5) 0.0174(16) Uani 1 2 d S T P
C4 C 1.0000 0.8933(11) 0.2036(6) 0.0217(19) Uani 1 2 d S T P
C3 C 1.0000 0.8675(11) 0.2923(7) 0.0200(16) Uani 1 2 d S T P
C2 C 1.0000 0.6895(11) 0.3146(5) 0.0179(17) Uani 1 2 d S T P
C1 C 1.0000 0.5529(12) 0.2564(6) 0.0208(17) Uani 1 2 d S T P
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'
N N 0.0061 0.0033 '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'
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
N1 S1 S2 97.7(3)
C2 S2 S1 91.7(3)
N2 S3 S4 99.2(3)
C4 S4 S3 91.2(3)
C1 N1 S1 116.9(7)
C5 N2 S3 114.5(6)
O1 C6 C1 124.4(9)
O1 C6 C5 122.0(8)
C1 C6 C5 113.6(7)
N2 C5 C4 120.7(8)
N2 C5 C6 119.5(8)
C4 C5 C6 119.8(8)
C3 C4 C5 127.0(8)
C3 C4 S4 118.6(7)
C5 C4 S4 114.4(7)
O2 C3 C4 124.3(8)
O2 C3 C2 123.3(9)
C4 C3 C2 112.3(8)
C1 C2 C3 125.6(8)
C1 C2 S2 114.7(6)
C3 C2 S2 119.7(7)
N1 C1 C2 119.0(8)
N1 C1 C6 119.4(8)
C2 C1 C6 121.6(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.609(9)
S1 S2 2.084(3)
S2 C2 1.712(8)
S3 N2 1.629(8)
S3 S4 2.088(4)
S4 C4 1.726(9)
N1 C1 1.313(11)
N2 C5 1.324(10)
O1 C6 1.218(10)
O2 C3 1.249(11)
C6 C1 1.472(12)
C6 C5 1.514(12)
C5 C4 1.425(12)
C4 C3 1.411(13)
C3 C2 1.450(11)
C2 C1 1.416(12)
