#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/84/2218414.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218414
loop_
_publ_author_name
'Kayed, Safa'a Fares'
'Farina, Yang'
'Kassim, Mohammad'
'Simpson, Jim'
_publ_section_title
;
 (E)-2-[1-(1-Benzothiophen-3-yl)ethylidene]hydrazinecarbothioamide
 methanol hemisolvate
;
_journal_coeditor_code           HB2725
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1022
_journal_page_last               o1023
_journal_paper_doi               10.1107/S160053680801297X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C11 H11 N3 S2, 0.5(C H4 O)'
_chemical_formula_sum            'C11.5 H13 N3 O S2'
_chemical_formula_weight         265.38
_chemical_name_systematic
;
(E)-2-[1-(1-Benzothiophen-3-yl)ethylidene]hydrazinecarbothioamide
methanol hemisolvate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.238(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.9438(12)
_cell_length_b                   17.7076(11)
_cell_length_c                   15.4145(10)
_cell_measurement_reflns_used    8980
_cell_measurement_temperature    92(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.25
_cell_volume                     4938.5(5)
_computing_cell_refinement
'APEX2 (Bruker, 2006) and SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury
(Macrae et al.,  2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,  2004)
and PLATON (Spek, 2003)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999)
;
_diffrn_ambient_temperature      92(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0855
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            65034
_diffrn_reflns_theta_full        27.14
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_min         1.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.713
_refine_diff_density_min         -2.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         10871
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0666
_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)+(0.1068P)²+8.4506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2026
_reflns_number_gt                8171
_reflns_number_total             10871
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2725.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218414
_cod_database_fobs_code          2218414
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1A 0.40620(18) 0.50684(18) 0.8528(2) 0.0201(7) Uani d . 1
C C2A 0.36631(19) 0.44650(19) 0.8029(2) 0.0241(7) Uani d . 1
H H2A 0.3746 0.4300 0.7480 0.029 Uiso calc R 1
C C3A 0.3144(2) 0.41176(19) 0.8364(2) 0.0254(7) Uani d . 1
H H3A 0.2872 0.3700 0.8046 0.030 Uiso calc R 1
C C4A 0.3010(2) 0.4368(2) 0.9163(3) 0.0263(8) Uani d . 1
H H4A 0.2643 0.4125 0.9370 0.032 Uiso calc R 1
C C5A 0.3402(2) 0.4960(2) 0.9651(3) 0.0252(7) Uani d . 1
H H5A 0.3309 0.5124 1.0193 0.030 Uiso calc R 1
C C6A 0.39438(18) 0.53217(18) 0.9341(2) 0.0212(7) Uani d . 1
S S1A 0.47650(5) 0.55720(5) 0.82797(6) 0.0235(2) Uani d . 1
C C7A 0.44278(18) 0.59319(19) 0.9744(2) 0.0224(7) Uani d . 1
H H7A 0.4422 0.6176 1.0291 0.027 Uiso calc R 1
C C8A 0.48976(18) 0.61239(18) 0.9258(2) 0.0200(7) Uani d . 1
C C9A 0.54827(18) 0.66957(18) 0.9473(2) 0.0207(7) Uani d . 1
C C10A 0.56188(18) 0.71682(19) 1.0314(2) 0.0223(7) Uani d . 1
H H10A 0.6108 0.7051 1.0729 0.033 Uiso calc R 1
H H10B 0.5241 0.7058 1.0614 0.033 Uiso calc R 1
H H10C 0.5596 0.7704 1.0150 0.033 Uiso calc R 1
N N1A 0.58542(15) 0.67430(16) 0.8893(2) 0.0213(6) Uani d . 1
N N2A 0.64370(16) 0.72396(16) 0.9091(2) 0.0211(6) Uani d D 1
H H2NA 0.659(2) 0.743(2) 0.9613(13) 0.025 Uiso d D 1
C C11A 0.67880(18) 0.73726(18) 0.8465(2) 0.0194(7) Uani d . 1
S S2A 0.75517(5) 0.79377(5) 0.87472(6) 0.02159(19) Uani d . 1
N N3A 0.65198(17) 0.70631(19) 0.7655(2) 0.0261(6) Uani d D 1
H H3N1 0.676(2) 0.714(2) 0.729(2) 0.031 Uiso d D 1
H H3N2 0.6187(17) 0.6733(18) 0.758(3) 0.031 Uiso d D 1
C C1B 0.1144(2) 0.9732(2) 0.6666(2) 0.0259(7) Uani d . 1
C C2B 0.1682(2) 1.0138(2) 0.7312(3) 0.0377(10) Uani d . 1
H H2B 0.1676 1.0165 0.7926 0.045 Uiso calc R 1
C C3B 0.2225(2) 1.0503(2) 0.7030(3) 0.0347(9) Uani d . 1
H H3B 0.2594 1.0787 0.7458 0.042 Uiso calc R 1
C C4B 0.2239(2) 1.0461(2) 0.6135(3) 0.0295(8) Uani d . 1
H H4B 0.2614 1.0720 0.5959 0.035 Uiso calc R 1
C C5B 0.1714(2) 1.0047(2) 0.5495(3) 0.0267(8) Uani d . 1
H H5B 0.1730 1.0015 0.4886 0.032 Uiso calc R 1
C C6B 0.11558(18) 0.96745(18) 0.5761(2) 0.0213(7) Uani d . 1
S S1B 0.04048(5) 0.92419(5) 0.68465(6) 0.0294(2) Uani d . 1
C C7B 0.05600(19) 0.92149(19) 0.5224(2) 0.0227(7) Uani d . 1
H H7B 0.0484 0.9107 0.4600 0.027 Uiso calc R 1
C C8B 0.01121(18) 0.89489(18) 0.5715(2) 0.0203(7) Uani d . 1
C C9B -0.05345(18) 0.84574(18) 0.5407(2) 0.0217(7) Uani d . 1
C C10B -0.0764(2) 0.8167(2) 0.4454(2) 0.0269(8) Uani d . 1
H H10D -0.0763 0.7614 0.4461 0.040 Uiso calc R 1
H H10E -0.0417 0.8349 0.4138 0.040 Uiso calc R 1
H H10F -0.1262 0.8349 0.4137 0.040 Uiso calc R 1
N N1B -0.08527(15) 0.83003(16) 0.6022(2) 0.0212(6) Uani d . 1
N N2B -0.14681(16) 0.78420(16) 0.5770(2) 0.0216(6) Uani d D 1
H H2NB -0.166(2) 0.768(2) 0.5243(13) 0.026 Uiso d D 1
C C11B -0.17783(18) 0.76294(19) 0.6424(2) 0.0202(7) Uani d . 1
S S2B -0.25346(5) 0.70679(5) 0.61499(6) 0.0227(2) Uani d . 1
N N3B -0.14553(16) 0.78669(17) 0.7263(2) 0.0233(6) Uani d D 1
H H3N3 -0.1059(13) 0.811(2) 0.735(3) 0.028 Uiso d D 1
H H3N4 -0.165(2) 0.770(2) 0.765(2) 0.028 Uiso d D 1
C C1C 0.3583(2) 0.7371(2) 0.6860(2) 0.0258(7) Uani d . 1
C C2C 0.4354(2) 0.7437(2) 0.7138(3) 0.0297(8) Uani d . 1
H H2C 0.4661 0.7002 0.7229 0.036 Uiso calc R 1
C C3C 0.4653(2) 0.8154(2) 0.7275(3) 0.0323(9) Uani d . 1
H H3C 0.5175 0.8214 0.7466 0.039 Uiso calc R 1
C C4C 0.4199(2) 0.8795(2) 0.7138(3) 0.0351(9) Uani d . 1
H H4C 0.4419 0.9281 0.7243 0.042 Uiso calc R 1
C C5C 0.3439(2) 0.8733(2) 0.6853(3) 0.0351(9) Uani d . 1
H H5C 0.3138 0.9172 0.6760 0.042 Uiso calc R 1
C C6C 0.3117(2) 0.8011(2) 0.6700(2) 0.0266(8) Uani d . 1
S S1C 0.30752(5) 0.65375(5) 0.66624(7) 0.0281(2) Uani d . 1
C C7C 0.2349(2) 0.7803(2) 0.6387(3) 0.0287(8) Uani d . 1
H H7C 0.1955 0.8158 0.6234 0.034 Uiso calc R 1
C C8C 0.2248(2) 0.70426(19) 0.6336(2) 0.0244(7) Uani d . 1
C C9C 0.1548(2) 0.6635(2) 0.6066(2) 0.0258(7) Uani d . 1
C C10C 0.0836(2) 0.7064(2) 0.5745(3) 0.0319(9) Uani d . 1
H H10G 0.0759 0.7230 0.5117 0.048 Uiso calc R 1
H H10H 0.0857 0.7506 0.6135 0.048 Uiso calc R 1
H H10I 0.0426 0.6737 0.5773 0.048 Uiso calc R 1
N N1C 0.16139(17) 0.59049(17) 0.6156(2) 0.0297(7) Uani d . 1
N N2C 0.09860(18) 0.54666(18) 0.5948(2) 0.0346(8) Uani d D 1
H H2NC 0.0583(14) 0.559(3) 0.556(3) 0.042 Uiso d D 1
C C11C 0.1060(2) 0.4744(2) 0.6250(3) 0.0298(8) Uani d . 1
S S2C 0.03402(6) 0.41383(6) 0.60223(8) 0.0448(3) Uani d . 1
N N3C 0.17357(19) 0.45564(18) 0.6749(2) 0.0322(8) Uani d D 1
H H3N5 0.2098(18) 0.485(2) 0.688(3) 0.050(15) Uiso d D 1
H H3N6 0.184(3) 0.4118(12) 0.696(3) 0.051(15) Uiso d D 1
C C1D 0.1294(2) 0.7575(2) 0.3394(3) 0.0292(8) Uani d . 1
C C2D 0.0537(2) 0.7729(3) 0.3080(3) 0.0398(10) Uani d . 1
H H2D 0.0181 0.7340 0.3021 0.048 Uiso calc R 1
C C3D 0.0326(3) 0.8473(3) 0.2858(3) 0.0445(11) Uani d . 1
H H3D -0.0184 0.8593 0.2636 0.053 Uiso calc R 1
C C4D 0.0844(3) 0.9040(3) 0.2953(3) 0.0412(10) Uani d . 1
H H4D 0.0682 0.9543 0.2798 0.049 Uiso calc R 1
C C5D 0.1592(2) 0.8893(2) 0.3268(3) 0.0347(9) Uani d . 1
H H5D 0.1940 0.9291 0.3334 0.042 Uiso calc R 1
C C6D 0.1832(2) 0.8146(2) 0.3492(2) 0.0277(8) Uani d . 1
S S1D 0.16977(5) 0.66977(5) 0.37222(7) 0.0311(2) Uani d . 1
C C7D 0.2567(2) 0.7850(2) 0.3818(2) 0.0272(8) Uani d . 1
H H7D 0.3000 0.8149 0.3917 0.033 Uiso calc R 1
C C8D 0.2576(2) 0.7092(2) 0.3971(2) 0.0252(7) Uani d . 1
C C9D 0.32188(19) 0.6605(2) 0.4331(2) 0.0245(7) Uani d . 1
C C10D 0.3983(2) 0.6910(2) 0.4466(3) 0.0341(9) Uani d . 1
H H10J 0.4262 0.6885 0.5112 0.051 Uiso calc R 1
H H10K 0.3951 0.7436 0.4261 0.051 Uiso calc R 1
H H10L 0.4234 0.6608 0.4113 0.051 Uiso calc R 1
N N1D 0.30772(17) 0.59253(17) 0.4530(2) 0.0291(7) Uani d . 1
N N2D 0.36755(19) 0.54664(19) 0.4909(3) 0.0376(8) Uani d D 1
H H2ND 0.4088(15) 0.560(3) 0.486(4) 0.060(17) Uiso d D 1
C C11D 0.3565(2) 0.4790(2) 0.5254(3) 0.0313(8) Uani d . 1
S S2D 0.43168(7) 0.42374(7) 0.57328(9) 0.0476(3) Uani d . 1
N N3D 0.28874(19) 0.45965(18) 0.5210(2) 0.0317(7) Uani d D 1
H H3N7 0.2536(17) 0.489(2) 0.496(3) 0.038 Uiso d D 1
H H3N8 0.284(3) 0.4170(13) 0.542(3) 0.038(13) Uiso d D 1
O O1S 0.1306(3) 0.4894(3) 0.4258(4) 0.0888(14) Uani d . 1
H H1S 0.0944 0.5187 0.4186 0.133 Uiso calc R 1
C C1S 0.1058(5) 0.4166(4) 0.4115(5) 0.087(2) Uani d . 1
H H1S1 0.1150 0.3907 0.4700 0.130 Uiso calc R 1
H H1S2 0.1321 0.3903 0.3743 0.130 Uiso calc R 1
H H1S3 0.0527 0.4166 0.3799 0.130 Uiso calc R 1
O O2S 0.5431(3) 0.5968(3) 0.6341(4) 0.0867(12) Uani d . 1
H H2S 0.5637 0.6279 0.6084 0.130 Uiso calc R 1
C C2S 0.5875(4) 0.5453(4) 0.6686(5) 0.0867(12) Uani d . 1
H H2S1 0.5690 0.4972 0.6390 0.130 Uiso calc R 1
H H2S2 0.5925 0.5417 0.7336 0.130 Uiso calc R 1
H H2S3 0.6357 0.5565 0.6604 0.130 Uiso calc R 1
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2A C1A C6A . 121.9(3)
C2A C1A S1A . 126.5(3)
C6A C1A S1A . 111.5(2)
C3A C2A C1A . 117.5(3)
C3A C2A H2A . 121.3
C1A C2A H2A . 121.3
C2A C3A C4A . 121.4(3)
C2A C3A H3A . 119.3
C4A C3A H3A . 119.3
C5A C4A C3A . 120.9(3)
C5A C4A H4A . 119.5
C3A C4A H4A . 119.5
C4A C5A C6A . 119.5(3)
C4A C5A H5A . 120.3
C6A C5A H5A . 120.3
C5A C6A C1A . 118.7(3)
C5A C6A C7A . 129.2(3)
C1A C6A C7A . 112.1(3)
C1A S1A C8A . 91.19(16)
C8A C7A C6A . 112.7(3)
C8A C7A H7A . 123.6
C6A C7A H7A . 123.6
C7A C8A C9A . 128.3(3)
C7A C8A S1A . 112.5(3)
C9A C8A S1A . 119.1(3)
N1A C9A C8A . 114.7(3)
N1A C9A C10A . 124.9(3)
C8A C9A C10A . 120.4(3)
C9A C10A H10A . 109.5
C9A C10A H10B . 109.5
H10A C10A H10B . 109.5
C9A C10A H10C . 109.5
H10A C10A H10C . 109.5
H10B C10A H10C . 109.5
C9A N1A N2A . 117.0(3)
C11A N2A N1A . 119.2(3)
C11A N2A H2NA . 120(3)
N1A N2A H2NA . 120(3)
N3A C11A N2A . 118.2(3)
N3A C11A S2A . 123.0(3)
N2A C11A S2A . 118.8(3)
C11A N3A H3N1 . 116(3)
C11A N3A H3N2 . 119(3)
H3N1 N3A H3N2 . 124(4)
C2B C1B C6B . 121.5(3)
C2B C1B S1B . 126.5(3)
C6B C1B S1B . 111.9(3)
C3B C2B C1B . 117.9(4)
C3B C2B H2B . 121.0
C1B C2B H2B . 121.0
C2B C3B C4B . 121.3(4)
C2B C3B H3B . 119.4
C4B C3B H3B . 119.4
C5B C4B C3B . 120.9(4)
C5B C4B H4B . 119.5
C3B C4B H4B . 119.5
C4B C5B C6B . 118.9(4)
C4B C5B H5B . 120.5
C6B C5B H5B . 120.5
C1B C6B C5B . 119.3(3)
C1B C6B C7B . 111.8(3)
C5B C6B C7B . 128.9(3)
C1B S1B C8B . 91.17(17)
C8B C7B C6B . 112.6(3)
C8B C7B H7B . 123.7
C6B C7B H7B . 123.7
C7B C8B C9B . 128.3(3)
C7B C8B S1B . 112.5(3)
C9B C8B S1B . 119.2(3)
N1B C9B C8B . 114.7(3)
N1B C9B C10B . 125.7(3)
C8B C9B C10B . 119.7(3)
C9B C10B H10D . 109.5
C9B C10B H10E . 109.5
H10D C10B H10E . 109.5
C9B C10B H10F . 109.5
H10D C10B H10F . 109.5
H10E C10B H10F . 109.5
C9B N1B N2B . 117.2(3)
C11B N2B N1B . 117.9(3)
C11B N2B H2NB . 118(3)
N1B N2B H2NB . 125(3)
N3B C11B N2B . 117.4(3)
N3B C11B S2B . 122.8(3)
N2B C11B S2B . 119.8(3)
C11B N3B H3N3 . 116(3)
C11B N3B H3N4 . 115(3)
H3N3 N3B H3N4 . 129(4)
C2C C1C C6C . 121.8(3)
C2C C1C S1C . 126.7(3)
C6C C1C S1C . 111.5(3)
C3C C2C C1C . 117.9(4)
C3C C2C H2C . 121.1
C1C C2C H2C . 121.1
C2C C3C C4C . 121.0(4)
C2C C3C H3C . 119.5
C4C C3C H3C . 119.5
C5C C4C C3C . 121.3(4)
C5C C4C H4C . 119.3
C3C C4C H4C . 119.3
C4C C5C C6C . 119.0(4)
C4C C5C H5C . 120.5
C6C C5C H5C . 120.5
C5C C6C C1C . 118.9(3)
C5C C6C C7C . 129.4(4)
C1C C6C C7C . 111.7(3)
C1C S1C C8C . 91.05(17)
C8C C7C C6C . 112.6(3)
C8C C7C H7C . 123.7
C6C C7C H7C . 123.7
C7C C8C C9C . 127.4(3)
C7C C8C S1C . 113.1(3)
C9C C8C S1C . 119.5(3)
N1C C9C C8C . 114.2(3)
N1C C9C C10C . 125.9(3)
C8C C9C C10C . 119.8(3)
C9C C10C H10G . 109.5
C9C C10C H10H . 109.5
H10G C10C H10H . 109.5
C9C C10C H10I . 109.5
H10G C10C H10I . 109.5
H10H C10C H10I . 109.5
C9C N1C N2C . 119.1(3)
C11C N2C N1C . 117.3(3)
C11C N2C H2NC . 117(3)
N1C N2C H2NC . 124(3)
N3C C11C N2C . 114.8(3)
N3C C11C S2C . 122.9(3)
N2C C11C S2C . 122.3(3)
C11C N3C H3N5 . 124(4)
C11C N3C H3N6 . 122(4)
H3N5 N3C H3N6 . 114(5)
C2D C1D C6D . 122.1(4)
C2D C1D S1D . 126.4(3)
C6D C1D S1D . 111.5(3)
C3D C2D C1D . 117.4(4)
C3D C2D H2D . 121.3
C1D C2D H2D . 121.3
C4D C3D C2D . 121.3(4)
C4D C3D H3D . 119.3
C2D C3D H3D . 119.3
C5D C4D C3D . 121.5(4)
C5D C4D H4D . 119.2
C3D C4D H4D . 119.2
C4D C5D C6D . 119.2(4)
C4D C5D H5D . 120.4
C6D C5D H5D . 120.4
C5D C6D C1D . 118.4(4)
C5D C6D C7D . 129.8(4)
C1D C6D C7D . 111.8(3)
C8D S1D C1D . 90.87(18)
C8D S1D S1B 4_575 137.93(13)
C1D S1D S1B 4_575 92.50(13)
C8D C7D C6D . 112.5(3)
C8D C7D H7D . 123.8
C6D C7D H7D . 123.8
C7D C8D C9D . 127.8(3)
C7D C8D S1D . 113.3(3)
C9D C8D S1D . 118.8(3)
N1D C9D C8D . 115.6(3)
N1D C9D C10D . 124.3(3)
C8D C9D C10D . 120.1(3)
C9D C10D H10J . 109.5
C9D C10D H10K . 109.5
H10J C10D H10K . 109.5
C9D C10D H10L . 109.5
H10J C10D H10L . 109.5
H10K C10D H10L . 109.5
C9D N1D N2D . 116.7(3)
C11D N2D N1D . 119.1(3)
C11D N2D H2ND . 123(4)
N1D N2D H2ND . 117(4)
N3D C11D N2D . 118.3(3)
N3D C11D S2D . 123.5(3)
N2D C11D S2D . 118.2(3)
C11D N3D H3N7 . 120(3)
C11D N3D H3N8 . 116(3)
H3N7 N3D H3N8 . 124(5)
C1S O1S H1S . 109.5
O1S C1S H1S1 . 109.5
O1S C1S H1S2 . 109.5
H1S1 C1S H1S2 . 109.5
O1S C1S H1S3 . 109.5
H1S1 C1S H1S3 . 109.5
H1S2 C1S H1S3 . 109.5
C2S O2S H2S . 109.5
O2S C2S H2S1 . 109.5
O2S C2S H2S2 . 109.5
H2S1 C2S H2S2 . 109.5
O2S C2S H2S3 . 109.5
H2S1 C2S H2S3 . 109.5
H2S2 C2S H2S3 . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1A C2A . 1.400(5)
C1A C6A . 1.410(5)
C1A S1A . 1.737(3)
C2A C3A . 1.384(5)
C2A H2A . 0.9500
C3A C4A . 1.400(5)
C3A H3A . 0.9500
C4A C5A . 1.373(5)
C4A H4A . 0.9500
C5A C6A . 1.407(5)
C5A H5A . 0.9500
C6A C7A . 1.434(5)
S1A C8A . 1.751(3)
C7A C8A . 1.366(5)
C7A H7A . 0.9500
C8A C9A . 1.465(5)
C9A N1A . 1.294(4)
C9A C10A . 1.501(5)
C10A H10A . 0.9800
C10A H10B . 0.9800
C10A H10C . 0.9800
N1A N2A . 1.373(4)
N2A C11A . 1.346(4)
N2A H2NA . 0.841(10)
C11A N3A . 1.319(4)
C11A S2A . 1.706(3)
N3A H3N1 . 0.839(10)
N3A H3N2 . 0.843(10)
C1B C2B . 1.395(5)
C1B C6B . 1.405(5)
C1B S1B . 1.739(4)
C2B C3B . 1.390(6)
C2B H2B . 0.9500
C3B C4B . 1.390(6)
C3B H3B . 0.9500
C4B C5B . 1.386(5)
C4B H4B . 0.9500
C5B C6B . 1.407(5)
C5B H5B . 0.9500
C6B C7B . 1.438(5)
S1B C8B . 1.746(3)
C7B C8B . 1.376(5)
C7B H7B . 0.9500
C8B C9B . 1.462(5)
C9B N1B . 1.296(5)
C9B C10B . 1.495(5)
C10B H10D . 0.9800
C10B H10E . 0.9800
C10B H10F . 0.9800
N1B N2B . 1.379(4)
N2B C11B . 1.362(4)
N2B H2NB . 0.839(10)
C11B N3B . 1.325(4)
C11B S2B . 1.692(3)
N3B H3N3 . 0.838(10)
N3B H3N4 . 0.839(10)
C1C C2C . 1.399(5)
C1C C6C . 1.413(5)
C1C S1C . 1.738(4)
C2C C3C . 1.381(5)
C2C H2C . 0.9500
C3C C4C . 1.401(6)
C3C H3C . 0.9500
C4C C5C . 1.379(6)
C4C H4C . 0.9500
C5C C6C . 1.406(5)
C5C H5C . 0.9500
C6C C7C . 1.439(5)
S1C C8C . 1.744(4)
C7C C8C . 1.359(5)
C7C H7C . 0.9500
C8C C9C . 1.458(5)
C9C N1C . 1.303(5)
C9C C10C . 1.499(5)
C10C H10G . 0.9800
C10C H10H . 0.9800
C10C H10I . 0.9800
N1C N2C . 1.376(4)
N2C C11C . 1.355(5)
N2C H2NC . 0.842(10)
C11C N3C . 1.326(5)
C11C S2C . 1.687(4)
N3C H3N5 . 0.842(10)
N3C H3N6 . 0.840(10)
C1D C2D . 1.396(5)
C1D C6D . 1.412(5)
C1D S1D . 1.740(4)
C2D C3D . 1.390(6)
C2D H2D . 0.9500
C3D C4D . 1.382(7)
C3D H3D . 0.9500
C4D C5D . 1.379(6)
C4D H4D . 0.9500
C5D C6D . 1.408(5)
C5D H5D . 0.9500
C6D C7D . 1.432(5)
S1D C8D . 1.739(4)
S1D S1B 4_575 3.5958(14)
C7D C8D . 1.362(5)
C7D H7D . 0.9500
C8D C9D . 1.461(5)
C9D N1D . 1.290(5)
C9D C10D . 1.500(5)
C10D H10J . 0.9800
C10D H10K . 0.9800
C10D H10L . 0.9800
N1D N2D . 1.376(4)
N2D C11D . 1.352(5)
N2D H2ND . 0.842(10)
C11D N3D . 1.311(5)
C11D S2D . 1.705(4)
N3D H3N7 . 0.841(10)
N3D H3N8 . 0.840(10)
O1S C1S . 1.367(8)
O1S H1S . 0.8400
C1S H1S1 . 0.9800
C1S H1S2 . 0.9800
C1S H1S3 . 0.9800
O2S C2S . 1.248(8)
O2S H2S . 0.8400
C2S H2S1 . 0.9800
C2S H2S2 . 0.9800
C2S H2S3 . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3A H3N2 N1A . 0.843(10) 2.29(4) 2.641(4) 105(3)
N3B H3N3 N1B . 0.838(10) 2.21(4) 2.617(4) 110(3)
N3C H3N5 N1C . 0.842(10) 2.22(5) 2.543(4) 102(4)
N3D H3N7 N1D . 0.841(10) 2.29(5) 2.643(4) 105(4)
N3A H3N1 S2B 1_655 0.839(10) 2.500(14) 3.325(3) 168(4)
N3B H3N4 S2A 1_455 0.839(10) 2.62(2) 3.367(3) 149(4)
N2B H2NB S2A 4_475 0.839(10) 2.585(13) 3.412(3) 169(4)
N3C H3N6 S2A 2_646 0.840(10) 2.76(4) 3.352(3) 129(4)
N3C H3N6 N3B 2_546 0.840(10) 2.72(3) 3.468(5) 149(5)
N2C H2NC S2C 3_566 0.842(10) 2.60(2) 3.392(3) 158(4)
N3D H3N8 S2A 2_646 0.840(10) 2.738(15) 3.563(3) 168(4)
N3D H3N7 O1S . 0.841(10) 2.26(3) 2.967(6) 142(4)
O1S H1S S2C 3_566 0.84 2.64 3.471(5) 169
O2S H2S S2D 3_666 0.84 2.97 3.389(6) 113
C3A H3A S2A 2_646 0.95 2.97 3.762(4) 142
C10A H10A S2B 4_676 0.98 2.91 3.613(3) 129
C2B H2B O1S 4_576 0.95 2.36 3.282(7) 163
C2S H2S1 N2D 3_666 0.98 2.74 3.266(9) 115
C10B H10F C~g~ 3_565 0.98 2.91 3.594(4) 129
