#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:19:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178430 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025176.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_4025176
loop_
_publ_author_name
'Jared F. Mike'
'Jeremy J. Inteman'
'Arkady Ellern'
'Malika Jeffries-EL'
_publ_section_title
;
 Facile Synthesis of 2,6-Disubstituted Benzobisthiazoles: Functional
 Monomers for the Design of Organic Semiconductors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              495
_journal_page_last               497
_journal_paper_doi               10.1021/jo9023864
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C18 H24 N2 O6 P2 S2'
_chemical_formula_weight         490.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.6930(10)
_cell_angle_beta                 112.5340(10)
_cell_angle_gamma                103.4750(10)
_cell_formula_units_Z            1
_cell_length_a                   7.9438(6)
_cell_length_b                   8.8059(12)
_cell_length_c                   9.4063(7)
_cell_measurement_reflns_used    3818
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      2.48
_cell_volume                     558.93(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6652
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0375
_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)+(0.0705P)²+0.2848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                2971
_reflns_number_total             3361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9023864_si_005.cif
_cod_data_source_block           jef13a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54581(6) 0.82211(4) 0.91297(4) 0.02108(11) Uani 1 1 d . . .
P1 P 0.72795(6) 0.93806(5) 0.64609(5) 0.01996(11) Uani 1 1 d . . .
O1 O 0.72463(18) 1.07380(14) 0.78221(14) 0.0258(2) Uani 1 1 d . . .
O2 O 0.91032(18) 0.89414(17) 0.74450(15) 0.0297(3) Uani 1 1 d . . .
O3 O 0.72576(18) 0.98125(15) 0.50267(14) 0.0270(2) Uani 1 1 d . . .
N1 N 0.49800(19) 0.54507(15) 0.71579(15) 0.0202(2) Uani 1 1 d . . .
C1 C 0.9622(3) 1.3339(2) 0.8259(3) 0.0427(5) Uani 1 1 d . . .
H1A H 0.9927 1.2809 0.7439 0.064 Uiso 1 1 calc R . .
H1B H 1.0752 1.4240 0.9084 0.064 Uiso 1 1 calc R . .
H1C H 0.8597 1.3750 0.7773 0.064 Uiso 1 1 calc R . .
C2 C 0.8980(3) 1.2114(2) 0.9013(2) 0.0341(4) Uani 1 1 d . . .
H2A H 1.0017 1.1699 0.9500 0.041 Uiso 1 1 calc R . .
H2B H 0.8722 1.2664 0.9870 0.041 Uiso 1 1 calc R . .
C3 C 0.5167(2) 0.76812(18) 0.59607(17) 0.0209(3) Uani 1 1 d . . .
H3 H 0.4111 0.7256 0.4932 0.025 Uiso 1 1 calc R . .
C4 C 0.5199(2) 0.69854(17) 0.72929(17) 0.0187(3) Uani 1 1 d . . .
C5 C 0.5210(2) 0.65097(16) 0.97757(17) 0.0181(3) Uani 1 1 d . . .
C6 C 0.5250(2) 0.64199(17) 1.12491(17) 0.0202(3) Uani 1 1 d . . .
H6 H 0.5416 0.7338 1.2049 0.024 Uiso 1 1 calc R . .
C7 C 0.4974(2) 0.51249(17) 0.85446(17) 0.0183(3) Uani 1 1 d . . .
C8 C 0.9952(3) 0.6852(3) 0.6054(3) 0.0515(6) Uani 1 1 d . . .
H8A H 0.9976 0.6303 0.6842 0.077 Uiso 1 1 calc R . .
H8B H 1.0883 0.6680 0.5682 0.077 Uiso 1 1 calc R . .
H8C H 0.8679 0.6410 0.5148 0.077 Uiso 1 1 calc R . .
C9 C 1.0443(3) 0.8650(2) 0.6813(2) 0.0326(4) Uani 1 1 d . . .
H9A H 1.1756 0.9109 0.7691 0.039 Uiso 1 1 calc R . .
H9B H 1.0385 0.9201 0.6010 0.039 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C4 89.40(7) . . ?
O3 P1 O2 114.86(7) . . ?
O3 P1 O1 116.72(7) . . ?
O2 P1 O1 102.70(7) . . ?
O3 P1 C3 112.46(7) . . ?
O2 P1 C3 107.15(7) . . ?
O1 P1 C3 101.57(7) . . ?
C2 O1 P1 122.17(12) . . ?
C9 O2 P1 122.48(11) . . ?
C4 N1 C7 111.01(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 111.78(15) . . ?
O1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 P1 116.22(10) . . ?
C4 C3 H3 121.9 . . ?
P1 C3 H3 121.9 . . ?
N1 C4 C3 123.16(13) . . ?
N1 C4 S1 115.87(11) . . ?
C3 C4 S1 120.94(10) . . ?
C6 C5 C7 122.78(12) . . ?
C6 C5 S1 128.21(11) . . ?
C7 C5 S1 109.00(10) . . ?
C5 C6 C7 116.14(12) . 2_667 ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 2_667 . ?
N1 C7 C6 124.21(12) . 2_667 ?
N1 C7 C5 114.72(12) . . ?
C6 C7 C5 121.07(12) 2_667 . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C8 110.59(16) . . ?
O2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.7331(14) . ?
S1 C4 1.7530(14) . ?
P1 O3 1.4690(11) . ?
P1 O2 1.5760(13) . ?
P1 O1 1.5777(12) . ?
P1 C3 1.7933(16) . ?
O1 C2 1.452(2) . ?
O2 C9 1.450(2) . ?
N1 C4 1.2948(18) . ?
N1 C7 1.3928(17) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.4967(19) . ?
C3 H3 0.9300 . ?
C5 C6 1.3928(18) . ?
C5 C7 1.4206(19) . ?
C6 C7 1.3930(19) 2_667 ?
C6 H6 0.9300 . ?
C7 C6 1.3930(19) 2_667 ?
C8 C9 1.487(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
