#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:10:05 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179442 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/39/4333936.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_4333936
loop_
_publ_author_name
'Kristina Lekin'
'Joanne W. L. Wong'
'Stephen M. Winter'
'Aaron Mailman'
'Paul A. Dube'
'Richard T. Oakley'
_publ_contact_author_email       oakley@uwaterloo.ca
_publ_contact_author_name        'Prof. R. T. Oakley'
_publ_section_title
;
 Bisdithiazolyl Radical Spin Ladders
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2188
_journal_page_last               2198
_journal_paper_doi               10.1021/ic302658c
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C11 H13 F N3 S4'
_chemical_formula_sum            'C11 H13 F N3 S4'
_chemical_formula_weight         334.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.334(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0351(17)
_cell_length_b                   4.6620(4)
_cell_length_c                   17.1669(16)
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.023
_cell_measurement_theta_min      2.398
_cell_volume                     1428.1(2)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12402
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0413
_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)+(0.0368P)²+0.5529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1671
_reflns_number_total             2647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302658c_si_002_1.cif
_cod_data_source_block           1d_hexyl_
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4333936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S2 S 0.46339(4) 0.16594(18) 0.36068(5) 0.0563(3) Uani 1 1 d .
S1 S 0.42405(5) 0.27921(19) 0.24368(5) 0.0588(3) Uani 1 1 d .
S4 S 0.33002(5) 0.7150(2) 0.58927(5) 0.0730(3) Uani 1 1 d .
S3 S 0.23772(6) 0.9757(2) 0.54838(7) 0.0858(4) Uani 1 1 d .
F1 F 0.43893(10) 0.2978(4) 0.52808(10) 0.0661(5) Uani 1 1 d .
N1 N 0.35607(13) 0.5010(5) 0.25992(14) 0.0503(7) Uani 1 1 d .
N3 N 0.23930(15) 0.9428(6) 0.45287(17) 0.0639(8) Uani 1 1 d .
N2 N 0.29782(12) 0.7263(5) 0.35596(14) 0.0435(6) Uani 1 1 d .
C1 C 0.35077(15) 0.5415(6) 0.33440(18) 0.0417(7) Uani 1 1 d .
C3 C 0.39246(16) 0.4399(7) 0.47175(18) 0.0471(8) Uani 1 1 d .
C2 C 0.39906(15) 0.3929(6) 0.39442(17) 0.0417(7) Uani 1 1 d .
C6 C 0.24840(15) 0.8843(6) 0.29471(18) 0.0500(8) Uani 1 1 d .
H6A H 0.2764 0.9323 0.2523 0.060 Uiso 1 1 calc R
H6B H 0.2332 1.0625 0.3169 0.060 Uiso 1 1 calc R
C7 C 0.17939(16) 0.7178(6) 0.26139(19) 0.0530(8) Uani 1 1 d .
H7A H 0.1535 0.6557 0.3042 0.064 Uiso 1 1 calc R
H7B H 0.1943 0.5479 0.2350 0.064 Uiso 1 1 calc R
C4 C 0.34052(16) 0.6261(7) 0.49376(17) 0.0480(8) Uani 1 1 d .
C8 C 0.12638(16) 0.8939(7) 0.20374(18) 0.0539(8) Uani 1 1 d .
H8A H 0.1532 0.9619 0.1623 0.065 Uiso 1 1 calc R
H8B H 0.1106 1.0606 0.2309 0.065 Uiso 1 1 calc R
C9 C 0.05742(16) 0.7316(7) 0.1667(2) 0.0602(9) Uani 1 1 d .
H9A H 0.0731 0.5725 0.1365 0.072 Uiso 1 1 calc R
H9B H 0.0326 0.6520 0.2083 0.072 Uiso 1 1 calc R
C5 C 0.29093(16) 0.7703(6) 0.43436(19) 0.0478(8) Uani 1 1 d .
C10 C 0.00223(18) 0.9094(8) 0.1138(2) 0.0722(11) Uani 1 1 d .
H10A H 0.0269 0.9852 0.0716 0.087 Uiso 1 1 calc R
H10B H -0.0124 1.0711 0.1437 0.087 Uiso 1 1 calc R
C11 C -0.06759(18) 0.7522(8) 0.0780(2) 0.0855(12) Uani 1 1 d .
H11A H -0.0998 0.8811 0.0452 0.128 Uiso 1 1 calc R
H11B H -0.0934 0.6805 0.1191 0.128 Uiso 1 1 calc R
H11C H -0.0540 0.5948 0.0469 0.128 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 S2 S1 90.94(10)
N1 S1 S2 98.73(9)
C4 S4 S3 90.70(11)
N3 S3 S4 98.72(11)
C1 N1 S1 114.5(2)
C5 N3 S3 114.5(2)
C1 N2 C5 121.2(2)
C1 N2 C6 119.5(2)
C5 N2 C6 119.3(2)
N1 C1 N2 120.3(3)
N1 C1 C2 120.8(3)
N2 C1 C2 119.0(3)
F1 C3 C2 118.8(3)
F1 C3 C4 119.3(3)
C2 C3 C4 121.9(3)
C3 C2 C1 119.5(3)
C3 C2 S2 125.4(2)
C1 C2 S2 115.0(2)
N2 C6 C7 113.2(2)
C6 C7 C8 112.2(2)
C3 C4 C5 119.0(3)
C3 C4 S4 126.0(2)
C5 C4 S4 115.0(2)
C7 C8 C9 114.0(2)
C10 C9 C8 114.3(3)
N3 C5 N2 119.7(3)
N3 C5 C4 120.9(3)
N2 C5 C4 119.4(3)
C9 C10 C11 114.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C2 1.731(3)
S2 S1 2.0985(12)
S1 N1 1.658(3)
S4 C4 1.728(3)
S4 S3 2.0978(15)
S3 N3 1.651(3)
F1 C3 1.357(3)
N1 C1 1.310(4)
N3 C5 1.304(4)
N2 C1 1.376(4)
N2 C5 1.385(4)
N2 C6 1.473(3)
C1 C2 1.428(4)
C3 C2 1.368(4)
C3 C4 1.370(4)
C6 C7 1.507(4)
C7 C8 1.514(4)
C4 C5 1.424(4)
C8 C9 1.515(4)
C9 C10 1.496(4)
C10 C11 1.509(4)
