#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/08/4320884.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_4320884
loop_
_publ_author_name
'Tristram Chivers'
'Monica P. Gibson'
'Masood Parvez'
'Ignacio Vargas-Baca'
_publ_contact_author
;
    Masood Parvez
    Department of Chemistry
    University of Calgary
    2500 University Drive N.W.
    Calgary, Alberta, Canada T2N 1N4  
;
_publ_contact_author_email       ' parvez@ucalgary.ca '
_publ_contact_author_fax         ' (403)289-9488 '
_publ_contact_author_phone       ' (403)220-5348 '
_publ_section_title
;
 Eight- and 16-Membered Cyanuric-Sulfanuric Ring Systems:
 C2N4S2→ C2N3S Ring Contraction
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1697
_journal_page_last               1704
_journal_paper_doi               10.1021/ic991314u
_journal_volume                  39
_journal_year                    2000
_chemical_formula_moiety         'C22 H13 F6 N3 O S'
_chemical_formula_sum            'C22 H13 F6 N3 O S'
_chemical_formula_weight         481.41
_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
_cell_angle_alpha                107.9999(19)
_cell_angle_beta                 105.796(2)
_cell_angle_gamma                94.300(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4667(8)
_cell_length_b                   11.3406(12)
_cell_length_c                   13.5470(14)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    193(2)
_cell_volume                     1033.79(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'ORTEP-1.05 for WindowsNT'
_computing_publication_material  'WinGX 1.62'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0838
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5129
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        '< 0.1'
_diffrn_standards_number         '50 phi-scan frames,end of data collection'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   'Gaussian integration'
_exptl_absorpt_process_details
;(a) W. R. Busing and H. A. Levy, Acta Crystallogr. 1957,
     10, 180-182.
 (b) P. Coppens, L. Leiserowitz and D. Rabinovich, Acta 
     Crystallogr. 1965, 18, 1035-1038. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0523
_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)+(0.0603P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                2309
_reflns_number_total             3890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic991314u_1.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4320884
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
S S 0.25382(11) 0.75842(8) -0.03788(6) 0.0340(2) Uani 1 1 d . . .
F1 F 0.2596(3) 0.0582(2) -0.50613(15) 0.0781(7) Uani 1 1 d . . .
F2 F 0.4582(3) 0.0244(2) -0.37927(16) 0.0696(7) Uani 1 1 d . . .
F3 F 0.1683(3) -0.0360(2) -0.41157(19) 0.0856(8) Uani 1 1 d . . .
F4 F 0.4277(3) 0.6837(2) 0.57478(16) 0.0880(8) Uani 1 1 d . . .
F5 F 0.1298(3) 0.6510(3) 0.53717(17) 0.0922(9) Uani 1 1 d . . .
F6 F 0.2798(4) 0.4967(2) 0.51125(17) 0.0840(8) Uani 1 1 d . . .
O O 0.4261(3) 0.8444(2) -0.00845(17) 0.0435(6) Uani 1 1 d . . .
N1 N 0.2067(3) 0.7378(2) 0.06342(19) 0.0351(6) Uani 1 1 d . . .
N2 N 0.2553(3) 0.5229(2) 0.00437(18) 0.0298(6) Uani 1 1 d . . .
N3 N 0.2505(3) 0.6263(2) -0.12671(19) 0.0367(6) Uani 1 1 d . . .
C1 C 0.2304(4) 0.6272(3) 0.0766(2) 0.0289(7) Uani 1 1 d . . .
C2 C 0.2578(4) 0.5273(3) -0.0934(2) 0.0304(7) Uani 1 1 d . . .
C11 C 0.0658(4) 0.8196(3) -0.1022(2) 0.0333(7) Uani 1 1 d . . .
C12 C -0.0913(4) 0.8327(3) -0.0670(2) 0.0390(8) Uani 1 1 d . . .
H12 H -0.0988 0.8090 -0.0066 0.047 Uiso 1 1 calc R . .
C13 C -0.2373(5) 0.8808(3) -0.1205(3) 0.0498(9) Uani 1 1 d . . .
H13 H -0.3451 0.8913 -0.0964 0.060 Uiso 1 1 calc R . .
C14 C -0.2260(5) 0.9133(4) -0.2081(3) 0.0598(10) Uani 1 1 d . . .
H14 H -0.3270 0.9455 -0.2451 0.072 Uiso 1 1 calc R . .
C15 C -0.0693(5) 0.8996(4) -0.2431(3) 0.0699(12) Uani 1 1 d . . .
H15 H -0.0632 0.9220 -0.3042 0.084 Uiso 1 1 calc R . .
C16 C 0.0782(5) 0.8536(4) -0.1899(3) 0.0551(10) Uani 1 1 d . . .
H16 H 0.1872 0.8455 -0.2131 0.066 Uiso 1 1 calc R . .
C21 C 0.2292(4) 0.6192(3) 0.1836(2) 0.0276(7) Uani 1 1 d . . .
C22 C 0.2175(4) 0.7260(3) 0.2665(2) 0.0342(7) Uani 1 1 d . . .
H22 H 0.2021 0.8024 0.2527 0.041 Uiso 1 1 calc R . .
C23 C 0.2284(4) 0.7202(3) 0.3680(2) 0.0393(8) Uani 1 1 d . . .
H23 H 0.2207 0.7927 0.4242 0.047 Uiso 1 1 calc R . .
C24 C 0.2504(4) 0.6088(3) 0.3886(2) 0.0356(7) Uani 1 1 d . . .
C25 C 0.2598(4) 0.5028(3) 0.3072(2) 0.0391(8) Uani 1 1 d . . .
H25 H 0.2728 0.4262 0.3210 0.047 Uiso 1 1 calc R . .
C26 C 0.2502(4) 0.5086(3) 0.2054(2) 0.0354(7) Uani 1 1 d . . .
H26 H 0.2580 0.4357 0.1497 0.042 Uiso 1 1 calc R . .
C27 C 0.2704(5) 0.6089(4) 0.5013(3) 0.0548(10) Uani 1 1 d . . .
C31 C 0.2679(4) 0.4070(3) -0.1742(2) 0.0283(7) Uani 1 1 d . . .
C32 C 0.2903(4) 0.3005(3) -0.1441(2) 0.0327(7) Uani 1 1 d . . .
H32 H 0.3007 0.3055 -0.0714 0.039 Uiso 1 1 calc R . .
C33 C 0.2973(4) 0.1882(3) -0.2193(2) 0.0359(7) Uani 1 1 d . . .
H33 H 0.3124 0.1160 -0.1986 0.043 Uiso 1 1 calc R . .
C34 C 0.2821(4) 0.1812(3) -0.3253(2) 0.0323(7) Uani 1 1 d . . .
C35 C 0.2612(4) 0.2861(3) -0.3559(2) 0.0369(8) Uani 1 1 d . . .
H35 H 0.2512 0.2806 -0.4287 0.044 Uiso 1 1 calc R . .
C36 C 0.2549(4) 0.3989(3) -0.2806(2) 0.0345(7) Uani 1 1 d . . .
H36 H 0.2417 0.4712 -0.3015 0.041 Uiso 1 1 calc R . .
C37 C 0.2912(5) 0.0586(3) -0.4046(2) 0.0404(8) Uani 1 1 d . . .
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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 1.00 0.040
0.00 -1.00 -1.00 0.040
0.00 1.00 -1.00 0.015
0.00 -1.00 1.00 0.015
1.00 0.00 -1.00 0.245
-1.00 0.00 1.00 0.245
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
O S N1 113.67(13) . . ?
O S N3 111.89(12) . . ?
N1 S N3 110.57(13) . . ?
O S C11 108.74(13) . . ?
N1 S C11 106.46(13) . . ?
N3 S C11 104.97(13) . . ?
C1 N1 S 116.36(19) . . ?
C1 N2 C2 117.8(3) . . ?
C2 N3 S 116.6(2) . . ?
N1 C1 N2 127.6(3) . . ?
N1 C1 C21 115.9(2) . . ?
N2 C1 C21 116.4(3) . . ?
N3 C2 N2 127.9(3) . . ?
N3 C2 C31 116.1(2) . . ?
N2 C2 C31 116.0(3) . . ?
C16 C11 C12 120.8(3) . . ?
C16 C11 S 118.0(2) . . ?
C12 C11 S 121.2(2) . . ?
C11 C12 C13 119.3(3) . . ?
C14 C13 C12 119.9(3) . . ?
C13 C14 C15 120.5(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C11 119.1(3) . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 C1 120.7(3) . . ?
C22 C21 C1 120.3(3) . . ?
C23 C22 C21 120.1(3) . . ?
C22 C23 C24 120.2(3) . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 C27 121.6(3) . . ?
C23 C24 C27 118.2(3) . . ?
C24 C25 C26 119.7(3) . . ?
C25 C26 C21 120.9(3) . . ?
F6 C27 F5 107.0(3) . . ?
F6 C27 F4 105.1(3) . . ?
F5 C27 F4 105.2(3) . . ?
F6 C27 C24 113.7(3) . . ?
F5 C27 C24 112.9(3) . . ?
F4 C27 C24 112.4(3) . . ?
C36 C31 C32 119.3(3) . . ?
C36 C31 C2 120.5(3) . . ?
C32 C31 C2 120.2(3) . . ?
C33 C32 C31 120.4(3) . . ?
C32 C33 C34 119.7(3) . . ?
C35 C34 C33 120.5(3) . . ?
C35 C34 C37 121.1(3) . . ?
C33 C34 C37 118.4(3) . . ?
C34 C35 C36 120.0(3) . . ?
C35 C36 C31 120.2(3) . . ?
F2 C37 F3 105.4(3) . . ?
F2 C37 F1 104.8(2) . . ?
F3 C37 F1 105.6(3) . . ?
F2 C37 C34 112.9(3) . . ?
F3 C37 C34 113.3(2) . . ?
F1 C37 C34 114.0(3) . . ?
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
S O 1.434(2) . ?
S N1 1.584(2) . ?
S N3 1.599(3) . ?
S C11 1.750(3) . ?
F1 C37 1.329(3) . ?
F2 C37 1.321(3) . ?
F3 C37 1.321(4) . ?
F4 C27 1.335(4) . ?
F5 C27 1.333(4) . ?
F6 C27 1.326(4) . ?
N1 C1 1.339(4) . ?
N2 C1 1.345(3) . ?
N2 C2 1.345(3) . ?
N3 C2 1.333(4) . ?
C1 C21 1.482(4) . ?
C2 C31 1.484(4) . ?
C11 C16 1.381(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.379(5) . ?
C15 C16 1.375(5) . ?
C21 C26 1.385(4) . ?
C21 C22 1.401(4) . ?
C22 C23 1.378(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.378(4) . ?
C24 C27 1.493(4) . ?
C25 C26 1.384(4) . ?
C31 C36 1.392(4) . ?
C31 C32 1.396(4) . ?
C32 C33 1.378(4) . ?
C33 C34 1.386(4) . ?
C34 C35 1.381(4) . ?
C34 C37 1.490(4) . ?
C35 C36 1.382(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O S N1 C1 -106.8(2) . . . . ?
N3 S N1 C1 20.0(3) . . . . ?
C11 S N1 C1 133.5(2) . . . . ?
O S N3 C2 111.6(2) . . . . ?
N1 S N3 C2 -16.2(3) . . . . ?
C11 S N3 C2 -130.7(2) . . . . ?
S N1 C1 N2 -13.4(4) . . . . ?
S N1 C1 C21 166.47(19) . . . . ?
C2 N2 C1 N1 0.1(4) . . . . ?
C2 N2 C1 C21 -179.8(2) . . . . ?
S N3 C2 N2 4.7(4) . . . . ?
S N3 C2 C31 -175.94(18) . . . . ?
C1 N2 C2 N3 4.7(4) . . . . ?
C1 N2 C2 C31 -174.6(2) . . . . ?
O S C11 C16 53.1(3) . . . . ?
N1 S C11 C16 176.0(3) . . . . ?
N3 S C11 C16 -66.8(3) . . . . ?
O S C11 C12 -127.3(3) . . . . ?
N1 S C11 C12 -4.5(3) . . . . ?
N3 S C11 C12 112.8(3) . . . . ?
C16 C11 C12 C13 -0.1(5) . . . . ?
S C11 C12 C13 -179.6(2) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C11 1.0(6) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
S C11 C16 C15 178.7(3) . . . . ?
N1 C1 C21 C26 179.2(3) . . . . ?
N2 C1 C21 C26 -0.9(4) . . . . ?
N1 C1 C21 C22 -4.5(4) . . . . ?
N2 C1 C21 C22 175.5(2) . . . . ?
C26 C21 C22 C23 0.5(4) . . . . ?
C1 C21 C22 C23 -175.9(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 -0.6(5) . . . . ?
C22 C23 C24 C27 177.2(3) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C27 C24 C25 C26 -176.7(3) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
C1 C21 C26 C25 176.3(2) . . . . ?
C25 C24 C27 F6 -5.9(5) . . . . ?
C23 C24 C27 F6 176.3(3) . . . . ?
C25 C24 C27 F5 -128.0(3) . . . . ?
C23 C24 C27 F5 54.2(4) . . . . ?
C25 C24 C27 F4 113.3(4) . . . . ?
C23 C24 C27 F4 -64.5(4) . . . . ?
N3 C2 C31 C36 -4.9(4) . . . . ?
N2 C2 C31 C36 174.5(2) . . . . ?
N3 C2 C31 C32 175.2(2) . . . . ?
N2 C2 C31 C32 -5.4(4) . . . . ?
C36 C31 C32 C33 -0.7(4) . . . . ?
C2 C31 C32 C33 179.2(2) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C32 C33 C34 C35 0.4(4) . . . . ?
C32 C33 C34 C37 179.7(3) . . . . ?
C33 C34 C35 C36 -0.1(4) . . . . ?
C37 C34 C35 C36 -179.4(3) . . . . ?
C34 C35 C36 C31 -0.6(4) . . . . ?
C32 C31 C36 C35 1.0(4) . . . . ?
C2 C31 C36 C35 -178.9(3) . . . . ?
C35 C34 C37 F2 113.3(3) . . . . ?
C33 C34 C37 F2 -66.0(4) . . . . ?
C35 C34 C37 F3 -126.9(3) . . . . ?
C33 C34 C37 F3 53.8(4) . . . . ?
C35 C34 C37 F1 -6.1(4) . . . . ?
C33 C34 C37 F1 174.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661108
