#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023412.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_4023412
loop_
_publ_author_name
'Stéphane Dufresne'
'W. G. Skene'
_publ_section_title
;
 Unsymmetric Pyrrole, Thiophene, and Furan-Conjugated Comonomers
 Prepared Using Azomethine Connections: Potential New Monomers
 for Alternating Homocoupled Products
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3859
_journal_page_last               3866
_journal_paper_doi               10.1021/jo8002503
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C20 H18 N2 O5 S2'
_chemical_formula_sum            'C20 H18 N2 O5 S2'
_chemical_formula_weight         430.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.0259(5)
_cell_length_b                   10.5149(6)
_cell_length_c                   46.432(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      15.00
_cell_volume                     3918.5(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            44153
_diffrn_reflns_theta_full        71.92
_diffrn_reflns_theta_max         71.92
_diffrn_reflns_theta_min         3.81
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  1080
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    2.780
_exptl_absorpt_correction_T_max  0.7685
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.423(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         7613
_refine_ls_number_restraints     853
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0383
_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)+(0.0720P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                6940
_reflns_number_total             7613
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8002503-File004.cif
_cod_data_source_block           sken34
_cod_database_code               4023412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S 0.11052(7) 0.47173(6) 0.011705(12) 0.02383(13) Uani 1 1 d . C .
O12 O 0.3992(3) 0.1842(2) 0.07041(4) 0.0431(5) Uani 1 1 d . C .
O13 O 0.3715(2) 0.06441(15) 0.03062(4) 0.0242(4) Uani 1 1 d . C .
O14 O 0.3644(2) 0.12941(16) -0.03922(4) 0.0290(4) Uani 1 1 d . . .
O15 O 0.5704(2) 0.21414(16) -0.01243(4) 0.0270(4) Uani 1 1 d . . .
N11 N 0.1273(3) 0.3768(2) 0.06701(4) 0.0248(5) Uani 1 1 d . C .
N12 N 0.2285(3) 0.41783(19) -0.04373(4) 0.0231(4) Uani 1 1 d . C .
C15 C 0.0593(3) 0.4790(2) 0.07678(5) 0.0255(5) Uani 1 1 d . . .
H15 H 0.0523 0.5518 0.0647 0.031 Uiso 1 1 calc R A 1
C16 C 0.1795(3) 0.3696(2) 0.03869(5) 0.0221(5) Uani 1 1 d . . .
C17 C 0.2815(3) 0.2749(2) 0.02760(5) 0.0208(5) Uani 1 1 d . C .
C18 C 0.3017(3) 0.2849(2) -0.00282(5) 0.0191(5) Uani 1 1 d . . .
C19 C 0.2181(3) 0.3855(2) -0.01482(5) 0.0220(5) Uani 1 1 d . C .
C110 C 0.1527(4) 0.5191(3) -0.05256(6) 0.0287(6) Uani 1 1 d . . .
H110 H 0.0885 0.5671 -0.0392 0.034 Uiso 1 1 calc R B 1
C115 C 0.3565(3) 0.1726(2) 0.04560(5) 0.0244(5) Uani 1 1 d . . .
C116 C 0.4538(3) -0.0429(2) 0.04463(6) 0.0298(6) Uani 1 1 d . . .
H11A H 0.5298 -0.0106 0.0597 0.036 Uiso 1 1 calc R C .
H11B H 0.5218 -0.0892 0.0303 0.036 Uiso 1 1 calc R . .
C117 C 0.3322(4) -0.1320(3) 0.05781(7) 0.0429(8) Uani 1 1 d . C .
H11C H 0.2776 -0.0906 0.0742 0.064 Uiso 1 1 calc R . .
H11D H 0.3905 -0.2085 0.0645 0.064 Uiso 1 1 calc R . .
H11E H 0.2482 -0.1558 0.0435 0.064 Uiso 1 1 calc R . .
C118 C 0.4123(3) 0.1999(2) -0.02043(5) 0.0216(5) Uani 1 1 d . C .
C119 C 0.6938(3) 0.1294(3) -0.02538(6) 0.0348(6) Uani 1 1 d . . .
H11F H 0.6623 0.1090 -0.0455 0.042 Uiso 1 1 calc R . .
H11G H 0.7012 0.0491 -0.0143 0.042 Uiso 1 1 calc R . .
C120 C 0.8588(4) 0.1984(3) -0.02471(7) 0.0390(7) Uani 1 1 d . . .
H12A H 0.8532 0.2732 -0.0373 0.058 Uiso 1 1 calc R . .
H12B H 0.9470 0.1414 -0.0315 0.058 Uiso 1 1 calc R . .
H12C H 0.8831 0.2254 -0.0050 0.058 Uiso 1 1 calc R . .
S11 S -0.0247(2) 0.35720(17) 0.12471(4) 0.0443(4) Uani 0.580(3) 1 d PU C 1
C11 C -0.1018(7) 0.4336(6) 0.15190(13) 0.0367(8) Uani 0.580(3) 1 d PU C 1
H11 H -0.1302 0.3940 0.1696 0.044 Uiso 0.580(3) 1 calc PR C 1
C12 C -0.1223(7) 0.5620(5) 0.14680(12) 0.0308(7) Uani 0.580(3) 1 d PU C 1
H12 H -0.1685 0.6214 0.1600 0.037 Uiso 0.580(3) 1 calc PR C 1
C13 C -0.0634(7) 0.5911(7) 0.11878(15) 0.0300(7) Uani 0.580(3) 1 d PU C 1
H13 H -0.0642 0.6736 0.1104 0.036 Uiso 0.580(3) 1 calc PR C 1
C14 C -0.0059(15) 0.4851(10) 0.1055(2) 0.0273(6) Uani 0.580(3) 1 d PU C 1
O11 O 0.2272(7) 0.4909(6) -0.10279(12) 0.0440(6) Uani 0.580(3) 1 d PU C 1
C111 C 0.1630(14) 0.5615(10) -0.0823(2) 0.0276(6) Uani 0.580(3) 1 d PU C 1
C112 C 0.0959(5) 0.7037(4) -0.09156(9) 0.0151(6) Uani 0.580(3) 1 d PU C 1
H112 H 0.0496 0.7752 -0.0819 0.018 Uiso 0.580(3) 1 calc PR C 1
C113 C 0.1459(7) 0.6660(5) -0.12559(12) 0.0315(7) Uani 0.580(3) 1 d PU C 1
H113 H 0.1158 0.7180 -0.1415 0.038 Uiso 0.580(3) 1 calc PR C 1
C114 C 0.2304(8) 0.5586(5) -0.12876(13) 0.0361(8) Uani 0.580(3) 1 d PU C 1
H114 H 0.2845 0.5317 -0.1459 0.043 Uiso 0.580(3) 1 calc PR C 1
O91 O 0.0274(8) 0.3886(6) 0.12419(14) 0.0370(11) Uani 0.420(3) 1 d PDU C 2
C911 C -0.006(2) 0.4879(14) 0.1052(3) 0.0275(6) Uani 0.420(3) 1 d PDU C 2
C912 C -0.0995(10) 0.5781(9) 0.1199(2) 0.0296(7) Uani 0.420(3) 1 d PDU C 2
H912 H -0.1381 0.6575 0.1128 0.035 Uiso 0.420(3) 1 calc PR C 2
C913 C -0.1263(11) 0.5244(7) 0.14862(17) 0.0305(7) Uani 0.420(3) 1 d PDU C 2
H913 H -0.1868 0.5621 0.1640 0.037 Uiso 0.420(3) 1 calc PR C 2
C914 C -0.0491(10) 0.4129(8) 0.14892(16) 0.0358(8) Uani 0.420(3) 1 d PDU C 2
H914 H -0.0487 0.3569 0.1650 0.043 Uiso 0.420(3) 1 calc PR C 2
S91 S 0.2653(4) 0.4829(3) -0.10706(6) 0.0439(5) Uani 0.420(3) 1 d PDU C 2
C91 C 0.2005(11) 0.5886(8) -0.13225(18) 0.0360(8) Uani 0.420(3) 1 d PDU C 2
H91 H 0.2267 0.5792 -0.1521 0.043 Uiso 0.420(3) 1 calc PR C 2
C92 C 0.1081(10) 0.6884(8) -0.12212(16) 0.0312(8) Uani 0.420(3) 1 d PDU C 2
H92 H 0.0699 0.7592 -0.1330 0.037 Uiso 0.420(3) 1 calc PR C 2
C93 C 0.0815(8) 0.6679(6) -0.09401(13) 0.0164(6) Uani 0.420(3) 1 d PDU C 2
H93 H 0.0141 0.7242 -0.0830 0.020 Uiso 0.420(3) 1 calc PR C 2
C94 C 0.1546(19) 0.5628(13) -0.0813(3) 0.0273(6) Uani 0.420(3) 1 d PDU C 2
S22 S -0.12512(7) 0.02866(6) 0.265670(12) 0.02418(13) Uani 1 1 d . F .
O22 O 0.1398(2) 0.32537(18) 0.20620(4) 0.0353(4) Uani 1 1 d . . .
O23 O 0.1315(2) 0.43790(16) 0.24756(4) 0.0254(4) Uani 1 1 d . . .
O24 O 0.1303(2) 0.37131(16) 0.31623(4) 0.0300(4) Uani 1 1 d . . .
O25 O 0.3362(2) 0.28147(15) 0.29007(4) 0.0256(4) Uani 1 1 d . . .
N21 N -0.1264(2) 0.1297(2) 0.21106(4) 0.0237(5) Uani 1 1 d . F .
N22 N -0.0008(2) 0.0800(2) 0.32057(4) 0.0233(4) Uani 1 1 d . F .
C215 C 0.1094(3) 0.3320(2) 0.23159(5) 0.0229(5) Uani 1 1 d . . .
C216 C 0.2030(3) 0.5492(2) 0.23318(6) 0.0296(6) Uani 1 1 d . . .
H21A H 0.2732 0.5210 0.2169 0.035 Uiso 1 1 calc R . .
H21B H 0.2751 0.5959 0.2469 0.035 Uiso 1 1 calc R . .
C217 C 0.0680(3) 0.6375(3) 0.22214(7) 0.0340(6) Uani 1 1 d . . .
H21C H 0.0040 0.5944 0.2070 0.051 Uiso 1 1 calc R . .
H21D H 0.1191 0.7145 0.2142 0.051 Uiso 1 1 calc R . .
H21E H -0.0065 0.6606 0.2380 0.051 Uiso 1 1 calc R . .
C218 C 0.1767(3) 0.3005(2) 0.29742(5) 0.0211(5) Uani 1 1 d . F .
C219 C 0.4620(3) 0.3631(3) 0.30373(7) 0.0344(6) Uani 1 1 d . . .
H21F H 0.4332 0.3779 0.3242 0.041 Uiso 1 1 calc R . .
H21G H 0.4673 0.4463 0.2938 0.041 Uiso 1 1 calc R . .
C220 C 0.6254(3) 0.2966(3) 0.30153(7) 0.0377(7) Uani 1 1 d . . .
H22A H 0.6292 0.2268 0.3155 0.056 Uiso 1 1 calc R . .
H22B H 0.7155 0.3568 0.3056 0.056 Uiso 1 1 calc R . .
H22C H 0.6389 0.2623 0.2820 0.056 Uiso 1 1 calc R . .
C210 C -0.0814(4) -0.0167(2) 0.33018(6) 0.0266(5) Uani 1 1 d . . .
H210 H -0.1500 -0.0632 0.3172 0.032 Uiso 1 1 calc R D 3
C25 C -0.1775(3) 0.0243(3) 0.20024(6) 0.0272(5) Uani 1 1 d . . .
H25 H -0.1592 -0.0521 0.2107 0.033 Uiso 1 1 calc R E 3
C26 C -0.0619(3) 0.1350(2) 0.23862(5) 0.0225(5) Uani 1 1 d . . .
C27 C 0.0401(3) 0.2286(2) 0.24960(5) 0.0212(5) Uani 1 1 d . F .
C28 C 0.0661(3) 0.2163(2) 0.27991(5) 0.0209(5) Uani 1 1 d . . .
C29 C -0.0138(3) 0.1141(2) 0.29189(5) 0.0217(5) Uani 1 1 d . F .
S21 S -0.32248(12) 0.15094(10) 0.155108(19) 0.0380(2) Uani 0.851(3) 1 d PDU F 3
C21 C -0.4045(5) 0.0617(4) 0.12768(8) 0.0416(8) Uani 0.851(3) 1 d PDU F 3
H21 H -0.4597 0.0970 0.1114 0.050 Uiso 0.851(3) 1 calc PR F 3
C22 C -0.3821(5) -0.0639(4) 0.13163(8) 0.0422(9) Uani 0.851(3) 1 d PDU F 3
H22 H -0.4165 -0.1268 0.1182 0.051 Uiso 0.851(3) 1 calc PR F 3
C23 C -0.3022(5) -0.0921(4) 0.15791(9) 0.0342(7) Uani 0.851(3) 1 d PDU F 3
H23 H -0.2794 -0.1760 0.1644 0.041 Uiso 0.851(3) 1 calc PR F 3
C24 C -0.2606(10) 0.0176(4) 0.17325(12) 0.0285(5) Uani 0.851(3) 1 d PDU F 3
O21 O 0.0347(5) 0.0038(4) 0.37889(9) 0.0427(7) Uani 0.851(3) 1 d PDU F 3
C211 C -0.0722(7) -0.0572(3) 0.35940(8) 0.0275(6) Uani 0.851(3) 1 d PDU F 3
C212 C -0.1503(5) -0.1606(3) 0.37262(7) 0.0333(6) Uani 0.851(3) 1 d PDU F 3
H212 H -0.2246 -0.2200 0.3641 0.040 Uiso 0.851(3) 1 calc PR F 3
C213 C -0.0933(5) -0.1574(4) 0.40219(7) 0.0355(7) Uani 0.851(3) 1 d PDU F 3
H213 H -0.1199 -0.2162 0.4170 0.043 Uiso 0.851(3) 1 calc PR F 3
C214 C 0.0051(5) -0.0541(3) 0.40437(8) 0.0386(8) Uani 0.851(3) 1 d PDU F 3
H214 H 0.0496 -0.0248 0.4221 0.046 Uiso 0.851(3) 1 calc PR F 3
O81 O -0.273(2) 0.1285(14) 0.1593(3) 0.0377(6) Uani 0.149(3) 1 d PDU F 4
C84 C -0.356(3) 0.1072(18) 0.1328(4) 0.0380(15) Uani 0.149(3) 1 d PDU F 4
H84 H -0.3729 0.1693 0.1182 0.046 Uiso 0.149(3) 1 calc PR F 4
C83 C -0.410(3) -0.017(2) 0.1313(4) 0.0371(14) Uani 0.149(3) 1 d PDU F 4
H83 H -0.4768 -0.0563 0.1170 0.044 Uiso 0.149(3) 1 calc PR F 4
C82 C -0.338(3) -0.0761(18) 0.1573(5) 0.0341(8) Uani 0.149(3) 1 d PDU F 4
H82 H -0.3433 -0.1635 0.1624 0.041 Uiso 0.149(3) 1 calc PR F 4
C81 C -0.263(6) 0.016(2) 0.1725(7) 0.0293(7) Uani 0.149(3) 1 d PDU F 4
S81 S 0.0029(12) 0.0190(8) 0.38227(19) 0.0419(7) Uani 0.149(3) 1 d PDU F 4
C814 C -0.082(4) -0.0772(19) 0.3581(4) 0.0287(7) Uani 0.149(3) 1 d PDU F 4
C813 C -0.122(3) -0.1980(17) 0.3688(4) 0.0328(8) Uani 0.149(3) 1 d PDU F 4
H813 H -0.1383 -0.2741 0.3582 0.039 Uiso 0.149(3) 1 calc PR F 4
C812 C -0.131(3) -0.182(2) 0.3980(4) 0.0355(8) Uani 0.149(3) 1 d PDU F 4
H812 H -0.2046 -0.2297 0.4099 0.043 Uiso 0.149(3) 1 calc PR F 4
C811 C -0.024(3) -0.0921(19) 0.4085(4) 0.0365(17) Uani 0.149(3) 1 d PDU F 4
H811 H 0.0259 -0.0916 0.4270 0.044 Uiso 0.149(3) 1 calc PR F 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C16 S12 C19 91.74(11) . . ?
C115 O13 C116 117.8(2) . . ?
C118 O15 C119 117.56(19) . . ?
C15 N11 C16 120.6(2) . . ?
C110 N12 C19 118.7(2) . . ?
N11 C15 C911 122.5(6) . . ?
N11 C15 C14 121.3(5) . . ?
N11 C15 H15 119.4 . . ?
C911 C15 H15 118.2 . . ?
C14 C15 H15 119.4 . . ?
N11 C16 C17 124.8(2) . . ?
N11 C16 S12 123.74(18) . . ?
C17 C16 S12 111.28(18) . . ?
C16 C17 C18 112.5(2) . . ?
C16 C17 C115 123.3(2) . . ?
C18 C17 C115 124.3(2) . . ?
C19 C18 C17 113.8(2) . . ?
C19 C18 C118 121.8(2) . . ?
C17 C18 C118 124.3(2) . . ?
C18 C19 N12 123.6(2) . . ?
C18 C19 S12 110.73(17) . . ?
N12 C19 S12 125.58(18) . . ?
N12 C110 C94 124.2(5) . . ?
N12 C110 C111 121.8(4) . . ?
N12 C110 H110 119.1 . . ?
C94 C110 H110 116.7 . . ?
C111 C110 H110 119.1 . . ?
O12 C115 O13 123.7(2) . . ?
O12 C115 C17 125.2(2) . . ?
O13 C115 C17 111.03(19) . . ?
O13 C116 C117 111.9(2) . . ?
O13 C116 H11A 109.2 . . ?
C117 C116 H11A 109.2 . . ?
O13 C116 H11B 109.2 . . ?
C117 C116 H11B 109.2 . . ?
H11A C116 H11B 107.9 . . ?
C116 C117 H11C 109.5 . . ?
C116 C117 H11D 109.5 . . ?
H11C C117 H11D 109.5 . . ?
C116 C117 H11E 109.5 . . ?
H11C C117 H11E 109.5 . . ?
H11D C117 H11E 109.5 . . ?
O14 C118 O15 125.1(2) . . ?
O14 C118 C18 124.8(2) . . ?
O15 C118 C18 110.2(2) . . ?
O15 C119 C120 107.0(2) . . ?
O15 C119 H11F 110.3 . . ?
C120 C119 H11F 110.3 . . ?
O15 C119 H11G 110.3 . . ?
C120 C119 H11G 110.3 . . ?
H11F C119 H11G 108.6 . . ?
C119 C120 H12A 109.5 . . ?
C119 C120 H12B 109.5 . . ?
H12A C120 H12B 109.5 . . ?
C119 C120 H12C 109.5 . . ?
H12A C120 H12C 109.5 . . ?
H12B C120 H12C 109.5 . . ?
C11 S11 C14 93.0(4) . . ?
C12 C11 S11 113.4(4) . . ?
C12 C11 H11 123.3 . . ?
S11 C11 H11 123.3 . . ?
C11 C12 C13 109.2(5) . . ?
C11 C12 H12 125.4 . . ?
C13 C12 H12 125.4 . . ?
C14 C13 C12 110.7(7) . . ?
C14 C13 H13 124.7 . . ?
C12 C13 H13 124.7 . . ?
C13 C14 C15 125.7(8) . . ?
C13 C14 S11 113.6(7) . . ?
C15 C14 S11 120.6(7) . . ?
C111 O11 C114 110.2(6) . . ?
O11 C111 C110 122.6(7) . . ?
O11 C111 C112 116.8(7) . . ?
C110 C111 C112 120.6(6) . . ?
C111 C112 C113 87.4(4) . . ?
C111 C112 H112 136.3 . . ?
C113 C112 H112 136.3 . . ?
C114 C113 C112 115.3(5) . . ?
C114 C113 H113 122.3 . . ?
C112 C113 H113 122.3 . . ?
C113 C114 O11 109.2(6) . . ?
C113 C114 H114 125.4 . . ?
O11 C114 H114 125.4 . . ?
C914 O91 C911 108.3(8) . . ?
C912 C911 O91 107.9(10) . . ?
C912 C911 C15 134.3(11) . . ?
O91 C911 C15 117.9(10) . . ?
C911 C912 C913 105.2(9) . . ?
C911 C912 H912 127.4 . . ?
C913 C912 H912 127.4 . . ?
C914 C913 C912 106.4(7) . . ?
C914 C913 H913 126.8 . . ?
C912 C913 H913 126.8 . . ?
C913 C914 O91 112.2(7) . . ?
C913 C914 H914 123.9 . . ?
O91 C914 H914 123.9 . . ?
C91 S91 C94 90.0(5) . . ?
C92 C91 S91 115.6(6) . . ?
C92 C91 H91 122.2 . . ?
S91 C91 H91 122.2 . . ?
C93 C92 C91 107.3(7) . . ?
C93 C92 H92 126.3 . . ?
C91 C92 H92 126.3 . . ?
C92 C93 C94 118.4(8) . . ?
C92 C93 H93 120.8 . . ?
C94 C93 H93 120.8 . . ?
C93 C94 C110 131.1(10) . . ?
C93 C94 S91 108.4(8) . . ?
C110 C94 S91 120.4(8) . . ?
C26 S22 C29 91.32(11) . . ?
C215 O23 C216 117.44(19) . . ?
C218 O25 C219 117.34(19) . . ?
C25 N21 C26 121.1(2) . . ?
C210 N22 C29 120.1(2) . . ?
O22 C215 O23 123.9(2) . . ?
O22 C215 C27 125.9(2) . . ?
O23 C215 C27 110.18(19) . . ?
O23 C216 C217 111.3(2) . . ?
O23 C216 H21A 109.4 . . ?
C217 C216 H21A 109.4 . . ?
O23 C216 H21B 109.4 . . ?
C217 C216 H21B 109.4 . . ?
H21A C216 H21B 108.0 . . ?
C216 C217 H21C 109.5 . . ?
C216 C217 H21D 109.5 . . ?
H21C C217 H21D 109.5 . . ?
C216 C217 H21E 109.5 . . ?
H21C C217 H21E 109.5 . . ?
H21D C217 H21E 109.5 . . ?
O24 C218 O25 124.8(2) . . ?
O24 C218 C28 125.2(2) . . ?
O25 C218 C28 109.89(19) . . ?
O25 C219 C220 107.5(2) . . ?
O25 C219 H21F 110.2 . . ?
C220 C219 H21F 110.2 . . ?
O25 C219 H21G 110.2 . . ?
C220 C219 H21G 110.2 . . ?
H21F C219 H21G 108.5 . . ?
C219 C220 H22A 109.5 . . ?
C219 C220 H22B 109.5 . . ?
H22A C220 H22B 109.5 . . ?
C219 C220 H22C 109.5 . . ?
H22A C220 H22C 109.5 . . ?
H22B C220 H22C 109.5 . . ?
N22 C210 C211 122.8(3) . . ?
N22 C210 C814 131.5(8) . . ?
N22 C210 H210 118.6 . . ?
C211 C210 H210 118.6 . . ?
C814 C210 H210 109.8 . . ?
N21 C25 C24 122.5(3) . . ?
N21 C25 C81 123.1(9) . . ?
N21 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C81 C25 H25 118.2 . . ?
C27 C26 N21 126.4(2) . . ?
C27 C26 S22 111.20(18) . . ?
N21 C26 S22 121.91(18) . . ?
C26 C27 C28 112.7(2) . . ?
C26 C27 C215 122.6(2) . . ?
C28 C27 C215 124.7(2) . . ?
C29 C28 C27 113.8(2) . . ?
C29 C28 C218 121.5(2) . . ?
C27 C28 C218 124.7(2) . . ?
C28 C29 N22 124.0(2) . . ?
C28 C29 S22 110.96(18) . . ?
N22 C29 S22 124.96(18) . . ?
C24 S21 C21 91.6(2) . . ?
C22 C21 S21 112.7(3) . . ?
C22 C21 H21 123.7 . . ?
S21 C21 H21 123.7 . . ?
C21 C22 C23 112.6(4) . . ?
C21 C22 H22 123.7 . . ?
C23 C22 H22 123.7 . . ?
C24 C23 C22 112.1(4) . . ?
C24 C23 H23 123.9 . . ?
C22 C23 H23 123.9 . . ?
C23 C24 C25 127.1(4) . . ?
C23 C24 S21 110.9(3) . . ?
C25 C24 S21 122.0(3) . . ?
C214 O21 C211 104.6(3) . . ?
C212 C211 O21 110.3(3) . . ?
C212 C211 C210 128.9(3) . . ?
O21 C211 C210 120.7(3) . . ?
C211 C212 C213 104.9(3) . . ?
C211 C212 H212 127.6 . . ?
C213 C212 H212 127.6 . . ?
C214 C213 C212 106.0(3) . . ?
C214 C213 H213 127.0 . . ?
C212 C213 H213 127.0 . . ?
C213 C214 O21 113.6(3) . . ?
C213 C214 H214 123.2 . . ?
O21 C214 H214 123.2 . . ?
C81 O81 C84 106.7(14) . . ?
C83 C84 O81 109.7(13) . . ?
C83 C84 H84 125.1 . . ?
O81 C84 H84 125.1 . . ?
C84 C83 C82 103.7(13) . . ?
C84 C83 H83 128.2 . . ?
C82 C83 H83 128.2 . . ?
C81 C82 C83 107.6(15) . . ?
C81 C82 H82 126.2 . . ?
C83 C82 H82 126.2 . . ?
O81 C81 C82 111.9(16) . . ?
O81 C81 C25 112.3(16) . . ?
C82 C81 C25 135.8(17) . . ?
C814 S81 C811 90.7(9) . . ?
C813 C814 C210 136.0(13) . . ?
C813 C814 S81 113.9(13) . . ?
C210 C814 S81 109.7(11) . . ?
C812 C813 C814 104.8(14) . . ?
C812 C813 H813 127.6 . . ?
C814 C813 H813 127.6 . . ?
C811 C812 C813 113.6(15) . . ?
C811 C812 H812 123.2 . . ?
C813 C812 H812 123.2 . . ?
C812 C811 S81 107.6(13) . . ?
C812 C811 H811 126.2 . . ?
S81 C811 H811 126.2 . . ?
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
S12 C16 1.740(2) . ?
S12 C19 1.756(2) . ?
O12 C115 1.208(3) . ?
O13 C115 1.339(3) . ?
O13 C116 1.461(3) . ?
O14 C118 1.208(3) . ?
O15 C118 1.331(3) . ?
O15 C119 1.461(3) . ?
N11 C15 1.288(3) . ?
N11 C16 1.382(3) . ?
N12 C110 1.293(3) . ?
N12 C19 1.387(3) . ?
C15 C911 1.424(14) . ?
C15 C14 1.435(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C17 C18 1.426(3) . ?
C17 C115 1.489(3) . ?
C18 C19 1.371(3) . ?
C18 C118 1.502(3) . ?
C110 C94 1.413(13) . ?
C110 C111 1.452(9) . ?
C110 H110 0.9500 . ?
C116 C117 1.485(4) . ?
C116 H11A 0.9900 . ?
C116 H11B 0.9900 . ?
C117 H11C 0.9800 . ?
C117 H11D 0.9800 . ?
C117 H11E 0.9800 . ?
C119 C120 1.510(4) . ?
C119 H11F 0.9900 . ?
C119 H11G 0.9900 . ?
C120 H12A 0.9800 . ?
C120 H12B 0.9800 . ?
C120 H12C 0.9800 . ?
S11 C11 1.619(6) . ?
S11 C14 1.620(10) . ?
C11 C12 1.380(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.418(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.354(11) . ?
C13 H13 0.9500 . ?
O11 C111 1.313(11) . ?
O11 C114 1.400(8) . ?
C111 C112 1.647(10) . ?
C112 C113 1.678(7) . ?
C112 H112 0.9500 . ?
C113 C114 1.326(7) . ?
C113 H113 0.9500 . ?
C114 H114 0.9500 . ?
O91 C914 1.327(9) . ?
O91 C911 1.391(14) . ?
C911 C912 1.388(14) . ?
C912 C913 1.465(11) . ?
C912 H912 0.9500 . ?
C913 C914 1.326(10) . ?
C913 H913 0.9500 . ?
C914 H914 0.9500 . ?
S91 C91 1.695(8) . ?
S91 C94 1.709(12) . ?
C91 C92 1.369(9) . ?
C91 H91 0.9500 . ?
C92 C93 1.340(9) . ?
C92 H92 0.9500 . ?
C93 C94 1.382(13) . ?
C93 H93 0.9500 . ?
S22 C26 1.756(2) . ?
S22 C29 1.757(2) . ?
O22 C215 1.206(3) . ?
O23 C215 1.350(3) . ?
O23 C216 1.465(3) . ?
O24 C218 1.206(3) . ?
O25 C218 1.340(3) . ?
O25 C219 1.469(3) . ?
N21 C25 1.284(3) . ?
N21 C26 1.382(3) . ?
N22 C210 1.286(3) . ?
N22 C29 1.383(3) . ?
C215 C27 1.480(3) . ?
C216 C217 1.516(4) . ?
C216 H21A 0.9900 . ?
C216 H21B 0.9900 . ?
C217 H21C 0.9800 . ?
C217 H21D 0.9800 . ?
C217 H21E 0.9800 . ?
C218 C28 1.495(3) . ?
C219 C220 1.490(4) . ?
C219 H21F 0.9900 . ?
C219 H21G 0.9900 . ?
C220 H22A 0.9800 . ?
C220 H22B 0.9800 . ?
C220 H22C 0.9800 . ?
C210 C211 1.424(5) . ?
C210 C814 1.444(19) . ?
C210 H210 0.9500 . ?
C25 C24 1.421(5) . ?
C25 C81 1.46(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(3) . ?
C27 C28 1.428(3) . ?
C28 C29 1.369(3) . ?
S21 C24 1.710(5) . ?
S21 C21 1.714(4) . ?
C21 C22 1.345(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.410(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(5) . ?
C23 H23 0.9500 . ?
O21 C214 1.352(5) . ?
O21 C211 1.402(5) . ?
C211 C212 1.397(5) . ?
C212 C213 1.448(4) . ?
C212 H212 0.9500 . ?
C213 C214 1.347(5) . ?
C213 H213 0.9500 . ?
C214 H214 0.9500 . ?
O81 C81 1.335(17) . ?
O81 C84 1.418(15) . ?
C84 C83 1.380(17) . ?
C84 H84 0.9500 . ?
C83 C82 1.473(16) . ?
C83 H83 0.9500 . ?
C82 C81 1.338(17) . ?
C82 H82 0.9500 . ?
S81 C814 1.658(16) . ?
S81 C811 1.701(15) . ?
C814 C813 1.400(16) . ?
C813 C812 1.369(16) . ?
C813 H813 0.9500 . ?
C812 C811 1.368(17) . ?
C812 H812 0.9500 . ?
C811 H811 0.9500 . ?
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
C16 N11 C15 C911 175.9(9) . . . . ?
C16 N11 C15 C14 175.6(6) . . . . ?
C15 N11 C16 C17 166.9(2) . . . . ?
C15 N11 C16 S12 -18.7(3) . . . . ?
C19 S12 C16 N11 -174.5(2) . . . . ?
C19 S12 C16 C17 0.56(18) . . . . ?
N11 C16 C17 C18 174.3(2) . . . . ?
S12 C16 C17 C18 -0.7(3) . . . . ?
N11 C16 C17 C115 -3.9(4) . . . . ?
S12 C16 C17 C115 -178.92(18) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C115 C17 C18 C19 178.7(2) . . . . ?
C16 C17 C18 C118 176.6(2) . . . . ?
C115 C17 C18 C118 -5.2(4) . . . . ?
C17 C18 C19 N12 175.9(2) . . . . ?
C118 C18 C19 N12 -0.4(4) . . . . ?
C17 C18 C19 S12 0.0(3) . . . . ?
C118 C18 C19 S12 -176.24(18) . . . . ?
C110 N12 C19 C18 -175.9(2) . . . . ?
C110 N12 C19 S12 -0.6(3) . . . . ?
C16 S12 C19 C18 -0.31(18) . . . . ?
C16 S12 C19 N12 -176.1(2) . . . . ?
C19 N12 C110 C94 179.6(9) . . . . ?
C19 N12 C110 C111 177.7(6) . . . . ?
C116 O13 C115 O12 -4.1(4) . . . . ?
C116 O13 C115 C17 175.79(19) . . . . ?
C16 C17 C115 O12 -32.7(4) . . . . ?
C18 C17 C115 O12 149.3(3) . . . . ?
C16 C17 C115 O13 147.5(2) . . . . ?
C18 C17 C115 O13 -30.5(3) . . . . ?
C115 O13 C116 C117 96.2(3) . . . . ?
C119 O15 C118 O14 -6.2(3) . . . . ?
C119 O15 C118 C18 174.1(2) . . . . ?
C19 C18 C118 O14 -66.7(3) . . . . ?
C17 C18 C118 O14 117.5(3) . . . . ?
C19 C18 C118 O15 113.0(2) . . . . ?
C17 C18 C118 O15 -62.8(3) . . . . ?
C118 O15 C119 C120 153.8(2) . . . . ?
C14 S11 C11 C12 2.3(6) . . . . ?
S11 C11 C12 C13 -1.8(7) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
C12 C13 C14 C15 178.6(9) . . . . ?
C12 C13 C14 S11 1.5(11) . . . . ?
N11 C15 C14 C13 172.6(8) . . . . ?
C911 C15 C14 C13 1(57) . . . . ?
N11 C15 C14 S11 -10.5(12) . . . . ?
C911 C15 C14 S11 178(100) . . . . ?
C11 S11 C14 C13 -2.2(9) . . . . ?
C11 S11 C14 C15 -179.4(9) . . . . ?
C114 O11 C111 C110 -176.3(8) . . . . ?
C114 O11 C111 C112 2.7(11) . . . . ?
N12 C110 C111 O11 10.7(13) . . . . ?
C94 C110 C111 O11 -137(23) . . . . ?
N12 C110 C111 C112 -168.3(5) . . . . ?
C94 C110 C111 C112 44(21) . . . . ?
O11 C111 C112 C113 3.2(9) . . . . ?
C110 C111 C112 C113 -177.8(8) . . . . ?
C111 C112 C113 C114 -8.8(7) . . . . ?
C112 C113 C114 O11 11.8(8) . . . . ?
C111 O11 C114 C113 -8.9(9) . . . . ?
C914 O91 C911 C912 3.1(15) . . . . ?
C914 O91 C911 C15 -177.6(11) . . . . ?
N11 C15 C911 C912 -171.4(14) . . . . ?
C14 C15 C911 C912 -163(60) . . . . ?
N11 C15 C911 O91 9.6(18) . . . . ?
C14 C15 C911 O91 18(57) . . . . ?
O91 C911 C912 C913 -2.2(14) . . . . ?
C15 C911 C912 C913 178.7(16) . . . . ?
C911 C912 C913 C914 0.6(12) . . . . ?
C912 C913 C914 O91 1.4(10) . . . . ?
C911 O91 C914 C913 -2.8(12) . . . . ?
C94 S91 C91 C92 4.6(9) . . . . ?
S91 C91 C92 C93 -5.4(10) . . . . ?
C91 C92 C93 C94 3.5(13) . . . . ?
C92 C93 C94 C110 178.2(13) . . . . ?
C92 C93 C94 S91 -0.3(14) . . . . ?
N12 C110 C94 C93 -179.7(11) . . . . ?
C111 C110 C94 C93 -147(23) . . . . ?
N12 C110 C94 S91 -1.4(16) . . . . ?
C111 C110 C94 S91 32(21) . . . . ?
C91 S91 C94 C93 -2.4(10) . . . . ?
C91 S91 C94 C110 179.0(12) . . . . ?
C216 O23 C215 O22 -2.5(4) . . . . ?
C216 O23 C215 C27 178.69(19) . . . . ?
C215 O23 C216 C217 94.0(3) . . . . ?
C219 O25 C218 O24 -7.1(3) . . . . ?
C219 O25 C218 C28 175.8(2) . . . . ?
C218 O25 C219 C220 158.9(2) . . . . ?
C29 N22 C210 C211 179.4(3) . . . . ?
C29 N22 C210 C814 175.5(18) . . . . ?
C26 N21 C25 C24 173.1(5) . . . . ?
C26 N21 C25 C81 173(3) . . . . ?
C25 N21 C26 C27 159.3(3) . . . . ?
C25 N21 C26 S22 -29.0(3) . . . . ?
C29 S22 C26 C27 0.68(19) . . . . ?
C29 S22 C26 N21 -172.1(2) . . . . ?
N21 C26 C27 C28 171.6(2) . . . . ?
S22 C26 C27 C28 -0.8(3) . . . . ?
N21 C26 C27 C215 -6.6(4) . . . . ?
S22 C26 C27 C215 -179.06(18) . . . . ?
O22 C215 C27 C26 -28.7(4) . . . . ?
O23 C215 C27 C26 150.0(2) . . . . ?
O22 C215 C27 C28 153.2(3) . . . . ?
O23 C215 C27 C28 -28.0(3) . . . . ?
C26 C27 C28 C29 0.5(3) . . . . ?
C215 C27 C28 C29 178.7(2) . . . . ?
C26 C27 C28 C218 177.2(2) . . . . ?
C215 C27 C28 C218 -4.6(4) . . . . ?
O24 C218 C28 C29 -68.5(3) . . . . ?
O25 C218 C28 C29 108.6(3) . . . . ?
O24 C218 C28 C27 115.0(3) . . . . ?
O25 C218 C28 C27 -67.9(3) . . . . ?
C27 C28 C29 N22 177.1(2) . . . . ?
C218 C28 C29 N22 0.3(4) . . . . ?
C27 C28 C29 S22 0.0(3) . . . . ?
C218 C28 C29 S22 -176.79(18) . . . . ?
C210 N22 C29 C28 179.3(2) . . . . ?
C210 N22 C29 S22 -4.1(3) . . . . ?
C26 S22 C29 C28 -0.38(19) . . . . ?
C26 S22 C29 N22 -177.4(2) . . . . ?
C24 S21 C21 C22 -1.6(4) . . . . ?
S21 C21 C22 C23 2.2(4) . . . . ?
C21 C22 C23 C24 -1.8(6) . . . . ?
C22 C23 C24 C25 -179.1(6) . . . . ?
C22 C23 C24 S21 0.6(7) . . . . ?
N21 C25 C24 C23 171.2(6) . . . . ?
C81 C25 C24 C23 -15(100) . . . . ?
N21 C25 C24 S21 -8.4(9) . . . . ?
C81 C25 C24 S21 165(100) . . . . ?
C21 S21 C24 C23 0.6(6) . . . . ?
C21 S21 C24 C25 -179.7(6) . . . . ?
C214 O21 C211 C212 -6.9(5) . . . . ?
C214 O21 C211 C210 177.0(4) . . . . ?
N22 C210 C211 C212 -179.0(4) . . . . ?
C814 C210 C211 C212 -18(10) . . . . ?
N22 C210 C211 O21 -3.7(7) . . . . ?
C814 C210 C211 O21 158(10) . . . . ?
O21 C211 C212 C213 3.0(5) . . . . ?
C210 C211 C212 C213 178.7(5) . . . . ?
C211 C212 C213 C214 2.1(5) . . . . ?
C212 C213 C214 O21 -6.9(5) . . . . ?
C211 O21 C214 C213 8.6(5) . . . . ?
C81 O81 C84 C83 5(3) . . . . ?
O81 C84 C83 C82 -6(3) . . . . ?
C84 C83 C82 C81 5(4) . . . . ?
C84 O81 C81 C82 -2(5) . . . . ?
C84 O81 C81 C25 179(3) . . . . ?
C83 C82 C81 O81 -2(5) . . . . ?
C83 C82 C81 C25 176(5) . . . . ?
N21 C25 C81 O81 4(5) . . . . ?
C24 C25 C81 O81 -3(100) . . . . ?
N21 C25 C81 C82 -175(4) . . . . ?
C24 C25 C81 C82 179(100) . . . . ?
N22 C210 C814 C813 -157(3) . . . . ?
C211 C210 C814 C813 -178(14) . . . . ?
N22 C210 C814 S81 16(3) . . . . ?
C211 C210 C814 S81 -5(8) . . . . ?
C811 S81 C814 C813 -4(3) . . . . ?
C811 S81 C814 C210 -179(2) . . . . ?
C210 C814 C813 C812 -167(3) . . . . ?
S81 C814 C813 C812 21(3) . . . . ?
C814 C813 C812 C811 -33(3) . . . . ?
C813 C812 C811 S81 30(3) . . . . ?
C814 S81 C811 C812 -14(2) . . . . ?
