#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:10:05 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179442 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/39/4333938.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_4333938
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         'C9 H9 F N3 S4'
_chemical_formula_sum            'C9 H9 F N3 S4'
_chemical_formula_weight         306.43
_chemical_name_common            FBPBu
_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                 108.6200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6371(12)
_cell_length_b                   4.8733(4)
_cell_length_c                   17.0938(13)
_cell_measurement_reflns_used    605
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.87
_cell_volume                     1234.44(17)
_computing_cell_refinement       ApexII
_computing_data_collection       ApexII
_computing_data_reduction        ApexII
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7825
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.8752
_exptl_absorpt_correction_T_min  0.8752
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0126P)²+0.6369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                2205
_reflns_number_total             2983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302658c_si_002_3.cif
_cod_data_source_block           1b_butyl_
_cod_database_code               4333938
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 0.45502(4) 0.20576(14) 0.35795(4) 0.05479(19) Uani 1 1 d .
S1 S 0.41120(5) 0.37071(15) 0.23800(4) 0.0589(2) Uani 1 1 d .
S4 S 0.30111(5) 0.64490(16) 0.57936(4) 0.0640(2) Uani 1 1 d .
S3 S 0.20331(6) 0.94801(17) 0.53340(5) 0.0710(2) Uani 1 1 d .
N2 N 0.26703(12) 0.7693(4) 0.34194(11) 0.0449(5) Uani 1 1 d .
C2 C 0.38159(15) 0.4159(5) 0.38733(13) 0.0417(5) Uani 1 1 d .
F1 F 0.42238(10) 0.2534(3) 0.52352(8) 0.0639(4) Uani 1 1 d .
C1 C 0.32705(15) 0.5919(5) 0.32416(13) 0.0422(5) Uani 1 1 d .
N1 N 0.33266(14) 0.5831(4) 0.24948(11) 0.0512(5) Uani 1 1 d .
C4 C 0.31336(15) 0.6028(5) 0.48308(13) 0.0445(5) Uani 1 1 d .
C5 C 0.25925(15) 0.7802(5) 0.42068(14) 0.0440(5) Uani 1 1 d .
N3 N 0.20312(14) 0.9538(5) 0.43633(13) 0.0591(6) Uani 1 1 d .
C3 C 0.37233(16) 0.4252(5) 0.46462(14) 0.0454(5) Uani 1 1 d .
C6 C 0.21161(16) 0.9525(5) 0.27703(14) 0.0505(6) Uani 1 1 d .
H6A H 0.2463 1.0081 0.2417 0.061 Uiso 1 1 calc R
H6B H 0.1971 1.1163 0.3025 0.061 Uiso 1 1 calc R
C8 C 0.06861(18) 1.0085(6) 0.15797(17) 0.0660(8) Uani 1 1 d .
H8A H 0.0538 1.1717 0.1835 0.079 Uiso 1 1 calc R
H8B H 0.1038 1.0651 0.1232 0.079 Uiso 1 1 calc R
C7 C 0.12522(16) 0.8187(5) 0.22493(15) 0.0558(6) Uani 1 1 d .
H7A H 0.0903 0.7637 0.2601 0.067 Uiso 1 1 calc R
H7B H 0.1397 0.6546 0.1995 0.067 Uiso 1 1 calc R
C9 C -0.0178(2) 0.8753(8) 0.1047(2) 0.0936(11) Uani 1 1 d .
H9A H -0.0511 1.0033 0.0635 0.140 Uiso 1 1 calc R
H9B H -0.0536 0.8221 0.1386 0.140 Uiso 1 1 calc R
H9C H -0.0036 0.7159 0.0782 0.140 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 90.97(8)
N1 S1 S2 98.38(7)
C4 S4 S3 90.93(9)
N3 S3 S4 98.94(8)
C1 N2 C5 120.87(19)
C1 N2 C6 119.50(18)
C5 N2 C6 119.62(19)
C3 C2 C1 119.1(2)
C3 C2 S2 125.60(18)
C1 C2 S2 115.32(16)
N1 C1 N2 119.9(2)
N1 C1 C2 120.5(2)
N2 C1 C2 119.59(19)
C1 N1 S1 114.66(17)
C3 C4 C5 119.5(2)
C3 C4 S4 125.48(18)
C5 C4 S4 114.93(18)
N3 C5 N2 119.7(2)
N3 C5 C4 121.2(2)
N2 C5 C4 119.2(2)
C5 N3 S3 114.01(18)
F1 C3 C4 119.4(2)
F1 C3 C2 118.8(2)
C4 C3 C2 121.7(2)
N2 C6 C7 112.6(2)
C9 C8 C7 112.7(2)
C6 C7 C8 112.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C2 1.729(2)
S2 S1 2.1030(10)
S1 N1 1.665(2)
S4 C4 1.729(2)
S4 S3 2.0906(11)
S3 N3 1.659(2)
N2 C1 1.379(3)
N2 C5 1.391(3)
N2 C6 1.471(3)
C2 C3 1.375(3)
C2 C1 1.429(3)
F1 C3 1.351(3)
C1 N1 1.308(3)
C4 C3 1.373(3)
C4 C5 1.423(3)
C5 N3 1.307(3)
C6 C7 1.508(3)
C8 C9 1.514(4)
C8 C7 1.517(3)
