#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/57/2225773.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_2225773
loop_
_publ_author_name
'Ballo, Daouda'
'Bouhfid, Rachid'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1-Benzyl-3-[(dimethylamino)methylene]-4-phenyl-1H-1,5-benzodiazepine-2(3H)-thione
;
_journal_coeditor_code           BT5234
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1019
_journal_paper_doi               10.1107/S160053681001175X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H23 N3 S'
_chemical_formula_moiety         'C25 H23 N3 S'
_chemical_formula_sum            'C25 H23 N3 S'
_chemical_formula_weight         397.52
_chemical_name_systematic
;
1-Benzyl-3-[(dimethylamino)methylene]-4-phenyl-1H-1,5-benzodiazepine-
2(3H)-thione
;
_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                 106.1360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.4740(8)
_cell_length_b                   10.2366(2)
_cell_length_c                   16.5650(5)
_cell_measurement_reflns_used    7420
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9
_cell_measurement_theta_min      2.6
_cell_volume                     4312.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX2 diffractometer'
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34616
_diffrn_reflns_theta_full        24.83
_diffrn_reflns_theta_max         24.83
_diffrn_reflns_theta_min         0.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0452
_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)+(0.0771P)²+0.7415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                5019
_reflns_number_total             7429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5234.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225773
_cod_database_fobs_code          2225773
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.68147(3) 0.23703(6) 0.88424(4) 0.0681(2) Uani d . 1 . .
S S2 0.82290(3) 0.28053(7) 0.73502(5) 0.0811(3) Uani d . 1 . .
N N1 0.66628(8) 0.46928(18) 0.94582(11) 0.0537(5) Uani d . 1 . .
N N2 0.60213(7) 0.65564(19) 0.83124(12) 0.0503(5) Uani d . 1 . .
N N3 0.66494(8) 0.48619(18) 0.65939(11) 0.0507(5) Uani d . 1 . .
N N4 0.81709(7) 0.52681(18) 0.78290(12) 0.0505(5) Uani d . 1 . .
N N5 0.89168(7) 0.6994(2) 0.73201(12) 0.0553(5) Uani d . 1 . .
N N6 0.84302(8) 0.48869(18) 0.51100(12) 0.0540(5) Uani d . 1 . .
C C1 0.66570(9) 0.3953(2) 0.87702(14) 0.0457(5) Uani d . 1 . .
C C2 0.68024(9) 0.6051(2) 0.94640(14) 0.0474(6) Uani d . 1 . .
C C3 0.72558(11) 0.6494(3) 1.00447(15) 0.0646(7) Uani d . 1 . .
H H3 0.7460 0.5914 1.0433 0.078 Uiso calc R 1 . .
C C4 0.74049(11) 0.7774(3) 1.00508(18) 0.0726(8) Uani d . 1 . .
H H4 0.7710 0.8059 1.0442 0.087 Uiso calc R 1 . .
C C5 0.71064(12) 0.8640(3) 0.94813(18) 0.0670(7) Uani d . 1 . .
H H5 0.7214 0.9504 0.9474 0.080 Uiso calc R 1 . .
C C6 0.66488(10) 0.8226(2) 0.89239(15) 0.0563(6) Uani d . 1 . .
H H6 0.6439 0.8825 0.8558 0.068 Uiso calc R 1 . .
C C7 0.64933(9) 0.6922(2) 0.88965(14) 0.0460(5) Uani d . 1 . .
C C8 0.60280(8) 0.5527(2) 0.78745(14) 0.0457(5) Uani d . 1 . .
C C9 0.64898(8) 0.4652(2) 0.79744(13) 0.0423(5) Uani d . 1 . .
C C10 0.66833(13) 0.4077(3) 1.02656(16) 0.0730(8) Uani d . 1 . .
H H10A 0.7037 0.4168 1.0636 0.088 Uiso calc R 1 . .
H H10B 0.6614 0.3150 1.0173 0.088 Uiso calc R 1 . .
C C11 0.63036(11) 0.4626(2) 1.06983(15) 0.0565(6) Uani d . 1 . .
C C12 0.63693(12) 0.4266(3) 1.15333(15) 0.0678(8) Uani d . 1 . .
H H12 0.6657 0.3759 1.1809 0.081 Uiso calc R 1 . .
C C13 0.60148(15) 0.4651(3) 1.1952(2) 0.0844(10) Uani d . 1 . .
H H13 0.6058 0.4386 1.2504 0.101 Uiso calc R 1 . .
C C14 0.55973(16) 0.5424(3) 1.1560(2) 0.0943(11) Uani d . 1 . .
H H14 0.5359 0.5691 1.1846 0.113 Uiso calc R 1 . .
C C15 0.55316(14) 0.5804(3) 1.0742(2) 0.0948(10) Uani d . 1 . .
H H15 0.5250 0.6338 1.0476 0.114 Uiso calc R 1 . .
C C16 0.58831(12) 0.5394(3) 1.03122(18) 0.0753(8) Uani d . 1 . .
H H16 0.5833 0.5643 0.9756 0.090 Uiso calc R 1 . .
C C17 0.55336(9) 0.5137(3) 0.72353(15) 0.0566(6) Uani d . 1 . .
C C18 0.51377(10) 0.6058(3) 0.69462(18) 0.0767(8) Uani d . 1 . .
H H18 0.5179 0.6903 0.7161 0.092 Uiso calc R 1 . .
C C19 0.46822(13) 0.5715(5) 0.6338(2) 0.1040(12) Uani d . 1 . .
H H19 0.4418 0.6331 0.6144 0.125 Uiso calc R 1 . .
C C20 0.46198(15) 0.4468(6) 0.6023(2) 0.1212(17) Uani d . 1 . .
H H20 0.4315 0.4245 0.5609 0.145 Uiso calc R 1 . .
C C21 0.50005(15) 0.3556(4) 0.6313(2) 0.1088(13) Uani d . 1 . .
H H21 0.4952 0.2707 0.6106 0.131 Uiso calc R 1 . .
C C22 0.54606(11) 0.3887(3) 0.69144(18) 0.0759(8) Uani d . 1 . .
H H22 0.5722 0.3263 0.7103 0.091 Uiso calc R 1 . .
C C23 0.67079(9) 0.4318(2) 0.73465(13) 0.0453(5) Uani d . 1 . .
H H23 0.6932 0.3600 0.7461 0.054 Uiso calc R 1 . .
C C24 0.63639(10) 0.6057(3) 0.63075(16) 0.0633(7) Uani d . 1 . .
H H24A 0.6359 0.6587 0.6783 0.095 Uiso calc R 1 . .
H H24B 0.6010 0.5850 0.5996 0.095 Uiso calc R 1 . .
H H24C 0.6533 0.6526 0.5953 0.095 Uiso calc R 1 . .
C C25 0.69212(14) 0.4298(3) 0.60257(19) 0.0846(10) Uani d . 1 . .
H H25A 0.7099 0.3514 0.6269 0.127 Uiso calc R 1 . .
H H25B 0.7173 0.4913 0.5933 0.127 Uiso calc R 1 . .
H H25C 0.6671 0.4093 0.5499 0.127 Uiso calc R 1 . .
C C26 0.82869(9) 0.4423(2) 0.72705(15) 0.0511(6) Uani d . 1 . .
C C27 0.80627(9) 0.6622(2) 0.76243(13) 0.0459(5) Uani d . 1 . .
C C28 0.75899(9) 0.7160(2) 0.76785(15) 0.0537(6) Uani d . 1 . .
H H28 0.7347 0.6633 0.7837 0.064 Uiso calc R 1 . .
C C29 0.74769(10) 0.8452(3) 0.75021(15) 0.0603(7) Uani d . 1 . .
H H29 0.7157 0.8792 0.7532 0.072 Uiso calc R 1 . .
C C30 0.78350(11) 0.9250(2) 0.72817(15) 0.0593(7) Uani d . 1 . .
H H30 0.7759 1.0129 0.7166 0.071 Uiso calc R 1 . .
C C31 0.83043(10) 0.8741(2) 0.72333(15) 0.0571(6) Uani d . 1 . .
H H31 0.8547 0.9289 0.7093 0.068 Uiso calc R 1 . .
C C32 0.84279(9) 0.7420(2) 0.73898(14) 0.0488(6) Uani d . 1 . .
C C33 0.89356(9) 0.5921(2) 0.69224(14) 0.0492(6) Uani d . 1 . .
C C34 0.84874(9) 0.5015(2) 0.66108(14) 0.0459(5) Uani d . 1 . .
C C35 0.80751(10) 0.4803(3) 0.86157(15) 0.0629(7) Uani d . 1 . .
H H35A 0.7961 0.3900 0.8542 0.076 Uiso calc R 1 . .
H H35B 0.7790 0.5310 0.8721 0.076 Uiso calc R 1 . .
C C36 0.85436(11) 0.4894(2) 0.93730(15) 0.0566(6) Uani d . 1 . .
C C37 0.85080(14) 0.4299(3) 1.01068(17) 0.0754(8) Uani d . 1 . .
H H37 0.8201 0.3861 1.0111 0.091 Uiso calc R 1 . .
C C38 0.89202(18) 0.4346(4) 1.0831(2) 0.0983(11) Uani d . 1 . .
H H38 0.8894 0.3918 1.1312 0.118 Uiso calc R 1 . .
C C39 0.93670(18) 0.5021(4) 1.0842(2) 0.1075(13) Uani d . 1 . .
H H39 0.9642 0.5062 1.1333 0.129 Uiso calc R 1 . .
C C40 0.94095(15) 0.5642(4) 1.0124(2) 0.1018(11) Uani d . 1 . .
H H40 0.9712 0.6108 1.0131 0.122 Uiso calc R 1 . .
C C41 0.89962(12) 0.5567(3) 0.93863(18) 0.0741(8) Uani d . 1 . .
H H41 0.9027 0.5975 0.8901 0.089 Uiso calc R 1 . .
C C42 0.94507(10) 0.5544(3) 0.68004(15) 0.0612(7) Uani d . 1 . .
C C43 0.98279(10) 0.6497(3) 0.68304(18) 0.0791(9) Uani d . 1 . .
H H43 0.9760 0.7359 0.6944 0.095 Uiso calc R 1 . .
C C44 1.03046(13) 0.6171(5) 0.6692(2) 0.1057(13) Uani d . 1 . .
H H44 1.0557 0.6813 0.6718 0.127 Uiso calc R 1 . .
C C45 1.04039(14) 0.4910(6) 0.6519(2) 0.1153(15) Uani d . 1 . .
H H45 1.0722 0.4698 0.6417 0.138 Uiso calc R 1 . .
C C46 1.00412(15) 0.3958(4) 0.6495(2) 0.1076(13) Uani d . 1 . .
H H46 1.0114 0.3099 0.6385 0.129 Uiso calc R 1 . .
C C47 0.95619(12) 0.4269(3) 0.6635(2) 0.0807(9) Uani d . 1 . .
H H47 0.9315 0.3617 0.6618 0.097 Uiso calc R 1 . .
C C48 0.83331(9) 0.4494(2) 0.58218(15) 0.0497(6) Uani d . 1 . .
H H48 0.8128 0.3746 0.5771 0.060 Uiso calc R 1 . .
C C49 0.86997(11) 0.6091(3) 0.50126(17) 0.0675(7) Uani d . 1 . .
H H49A 0.8668 0.6709 0.5432 0.101 Uiso calc R 1 . .
H H49B 0.8544 0.6448 0.4464 0.101 Uiso calc R 1 . .
H H49C 0.9065 0.5910 0.5078 0.101 Uiso calc R 1 . .
C C50 0.82724(13) 0.4069(3) 0.43621(17) 0.0795(9) Uani d . 1 . .
H H50A 0.8016 0.3445 0.4426 0.119 Uiso calc R 1 . .
H H50B 0.8574 0.3617 0.4288 0.119 Uiso calc R 1 . .
H H50C 0.8124 0.4606 0.3879 0.119 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 119.02(18) ?
C1 N1 C10 . . 120.81(19) ?
C2 N1 C10 . . 117.75(19) ?
C8 N2 C7 . . 117.40(19) ?
C23 N3 C24 . . 125.0(2) ?
C23 N3 C25 . . 119.3(2) ?
C24 N3 C25 . . 115.5(2) ?
C26 N4 C27 . . 121.32(18) ?
C26 N4 C35 . . 121.48(19) ?
C27 N4 C35 . . 116.62(19) ?
C33 N5 C32 . . 118.36(19) ?
C48 N6 C49 . . 125.0(2) ?
C48 N6 C50 . . 119.8(2) ?
C49 N6 C50 . . 115.2(2) ?
N1 C1 C9 . . 114.40(19) ?
N1 C1 S1 . . 122.29(17) ?
C9 C1 S1 . . 123.29(17) ?
C7 C2 C3 . . 119.6(2) ?
C7 C2 N1 . . 121.0(2) ?
C3 C2 N1 . . 119.4(2) ?
C4 C3 C2 . . 120.6(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 119.7(3) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C7 . . 121.1(2) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C2 C7 C6 . . 118.7(2) ?
C2 C7 N2 . . 122.8(2) ?
C6 C7 N2 . . 118.5(2) ?
N2 C8 C9 . . 124.9(2) ?
N2 C8 C17 . . 118.3(2) ?
C9 C8 C17 . . 116.8(2) ?
C23 C9 C1 . . 118.7(2) ?
C23 C9 C8 . . 125.1(2) ?
C1 C9 C8 . . 115.48(18) ?
N1 C10 C11 . . 114.6(2) ?
N1 C10 H10A . . 108.6 ?
C11 C10 H10A . . 108.6 ?
N1 C10 H10B . . 108.6 ?
C11 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.6 ?
C16 C11 C12 . . 118.4(3) ?
C16 C11 C10 . . 124.0(2) ?
C12 C11 C10 . . 117.4(2) ?
C13 C12 C11 . . 120.8(3) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C14 C13 C12 . . 120.2(3) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.7(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.1(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 120.7(3) ?
C11 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C22 C17 C18 . . 119.0(3) ?
C22 C17 C8 . . 121.6(2) ?
C18 C17 C8 . . 119.4(3) ?
C19 C18 C17 . . 119.9(3) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C20 C19 C18 . . 120.1(4) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C21 C20 C19 . . 120.4(4) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 C22 . . 120.2(4) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C17 C22 C21 . . 120.4(3) ?
C17 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
N3 C23 C9 . . 130.0(2) ?
N3 C23 H23 . . 115.0 ?
C9 C23 H23 . . 115.0 ?
N3 C24 H24A . . 109.5 ?
N3 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
N3 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
N3 C25 H25A . . 109.5 ?
N3 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
N3 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
N4 C26 C34 . . 116.01(19) ?
N4 C26 S2 . . 122.16(17) ?
C34 C26 S2 . . 121.78(18) ?
C28 C27 C32 . . 119.3(2) ?
C28 C27 N4 . . 119.3(2) ?
C32 C27 N4 . . 121.3(2) ?
C29 C28 C27 . . 121.0(2) ?
C29 C28 H28 . . 119.5 ?
C27 C28 H28 . . 119.5 ?
C28 C29 C30 . . 120.3(2) ?
C28 C29 H29 . . 119.9 ?
C30 C29 H29 . . 119.9 ?
C31 C30 C29 . . 119.5(2) ?
C31 C30 H30 . . 120.2 ?
C29 C30 H30 . . 120.2 ?
C30 C31 C32 . . 121.7(2) ?
C30 C31 H31 . . 119.1 ?
C32 C31 H31 . . 119.1 ?
N5 C32 C31 . . 117.3(2) ?
N5 C32 C27 . . 124.5(2) ?
C31 C32 C27 . . 118.1(2) ?
N5 C33 C42 . . 117.3(2) ?
N5 C33 C34 . . 124.8(2) ?
C42 C33 C34 . . 117.9(2) ?
C48 C34 C26 . . 118.4(2) ?
C48 C34 C33 . . 125.2(2) ?
C26 C34 C33 . . 114.7(2) ?
N4 C35 C36 . . 114.4(2) ?
N4 C35 H35A . . 108.7 ?
C36 C35 H35A . . 108.7 ?
N4 C35 H35B . . 108.7 ?
C36 C35 H35B . . 108.7 ?
H35A C35 H35B . . 107.6 ?
C41 C36 C37 . . 118.5(3) ?
C41 C36 C35 . . 123.8(2) ?
C37 C36 C35 . . 117.6(3) ?
C38 C37 C36 . . 121.1(3) ?
C38 C37 H37 . . 119.4 ?
C36 C37 H37 . . 119.4 ?
C39 C38 C37 . . 120.2(3) ?
C39 C38 H38 . . 119.9 ?
C37 C38 H38 . . 119.9 ?
C38 C39 C40 . . 119.9(4) ?
C38 C39 H39 . . 120.0 ?
C40 C39 H39 . . 120.0 ?
C39 C40 C41 . . 119.8(4) ?
C39 C40 H40 . . 120.1 ?
C41 C40 H40 . . 120.1 ?
C36 C41 C40 . . 120.5(3) ?
C36 C41 H41 . . 119.7 ?
C40 C41 H41 . . 119.7 ?
C47 C42 C43 . . 118.7(3) ?
C47 C42 C33 . . 121.8(2) ?
C43 C42 C33 . . 119.5(3) ?
C44 C43 C42 . . 120.3(3) ?
C44 C43 H43 . . 119.8 ?
C42 C43 H43 . . 119.8 ?
C45 C44 C43 . . 120.0(4) ?
C45 C44 H44 . . 120.0 ?
C43 C44 H44 . . 120.0 ?
C46 C45 C44 . . 120.5(4) ?
C46 C45 H45 . . 119.7 ?
C44 C45 H45 . . 119.7 ?
C45 C46 C47 . . 120.1(4) ?
C45 C46 H46 . . 120.0 ?
C47 C46 H46 . . 120.0 ?
C42 C47 C46 . . 120.3(3) ?
C42 C47 H47 . . 119.9 ?
C46 C47 H47 . . 119.9 ?
N6 C48 C34 . . 130.4(2) ?
N6 C48 H48 . . 114.8 ?
C34 C48 H48 . . 114.8 ?
N6 C49 H49A . . 109.5 ?
N6 C49 H49B . . 109.5 ?
H49A C49 H49B . . 109.5 ?
N6 C49 H49C . . 109.5 ?
H49A C49 H49C . . 109.5 ?
H49B C49 H49C . . 109.5 ?
N6 C50 H50A . . 109.5 ?
N6 C50 H50B . . 109.5 ?
H50A C50 H50B . . 109.5 ?
N6 C50 H50C . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.669(2) ?
S2 C26 . 1.672(2) ?
N1 C1 . 1.365(3) ?
N1 C2 . 1.438(3) ?
N1 C10 . 1.466(3) ?
N2 C8 . 1.283(3) ?
N2 C7 . 1.402(3) ?
N3 C23 . 1.334(3) ?
N3 C24 . 1.447(3) ?
N3 C25 . 1.454(3) ?
N4 C26 . 1.362(3) ?
N4 C27 . 1.437(3) ?
N4 C35 . 1.474(3) ?
N5 C33 . 1.289(3) ?
N5 C32 . 1.400(3) ?
N6 C48 . 1.336(3) ?
N6 C49 . 1.455(3) ?
N6 C50 . 1.457(3) ?
C1 C9 . 1.457(3) ?
C2 C7 . 1.386(3) ?
C2 C3 . 1.389(3) ?
C3 C4 . 1.368(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.487(3) ?
C8 C17 . 1.491(3) ?
C9 C23 . 1.366(3) ?
C10 C11 . 1.497(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.368(4) ?
C11 C12 . 1.395(3) ?
C12 C13 . 1.370(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.367(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.374(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C22 . 1.378(4) ?
C17 C18 . 1.392(4) ?
C18 C19 . 1.384(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.371(6) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.360(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.384(4) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C26 C34 . 1.472(3) ?
C27 C28 . 1.393(3) ?
C27 C32 . 1.400(3) ?
C28 C29 . 1.370(3) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.375(3) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.370(4) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.399(3) ?
C31 H31 . 0.9300 ?
C33 C42 . 1.484(3) ?
C33 C34 . 1.481(3) ?
C34 C48 . 1.365(3) ?
C35 C36 . 1.502(3) ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
C36 C41 . 1.377(4) ?
C36 C37 . 1.386(3) ?
C37 C38 . 1.380(5) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.365(5) ?
C38 H38 . 0.9300 ?
C39 C40 . 1.381(5) ?
C39 H39 . 0.9300 ?
C40 C41 . 1.397(4) ?
C40 H40 . 0.9300 ?
C41 H41 . 0.9300 ?
C42 C47 . 1.382(4) ?
C42 C43 . 1.387(4) ?
C43 C44 . 1.384(4) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.364(6) ?
C44 H44 . 0.9300 ?
C45 C46 . 1.361(6) ?
C45 H45 . 0.9300 ?
C46 C47 . 1.388(4) ?
C46 H46 . 0.9300 ?
C47 H47 . 0.9300 ?
C48 H48 . 0.9300 ?
C49 H49A . 0.9600 ?
C49 H49B . 0.9600 ?
C49 H49C . 0.9600 ?
C50 H50A . 0.9600 ?
C50 H50B . 0.9600 ?
C50 H50C . 0.9600 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C9 . . . . -34.4(3) ?
C10 N1 C1 C9 . . . . 163.6(2) ?
C2 N1 C1 S1 . . . . 147.05(18) ?
C10 N1 C1 S1 . . . . -14.9(3) ?
C1 N1 C2 C7 . . . . 64.1(3) ?
C10 N1 C2 C7 . . . . -133.4(2) ?
C1 N1 C2 C3 . . . . -115.5(2) ?
C10 N1 C2 C3 . . . . 47.0(3) ?
C7 C2 C3 C4 . . . . -1.3(4) ?
N1 C2 C3 C4 . . . . 178.4(2) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C3 C4 C5 C6 . . . . 2.1(4) ?
C4 C5 C6 C7 . . . . -3.2(4) ?
C3 C2 C7 C6 . . . . 0.2(3) ?
N1 C2 C7 C6 . . . . -179.43(19) ?
C3 C2 C7 N2 . . . . -177.7(2) ?
N1 C2 C7 N2 . . . . 2.7(3) ?
C5 C6 C7 C2 . . . . 2.0(3) ?
C5 C6 C7 N2 . . . . -180.0(2) ?
C8 N2 C7 C2 . . . . -48.7(3) ?
C8 N2 C7 C6 . . . . 133.4(2) ?
C7 N2 C8 C9 . . . . 3.7(3) ?
C7 N2 C8 C17 . . . . -178.59(19) ?
N1 C1 C9 C23 . . . . 146.7(2) ?
S1 C1 C9 C23 . . . . -34.8(3) ?
N1 C1 C9 C8 . . . . -43.1(3) ?
S1 C1 C9 C8 . . . . 135.43(19) ?
N2 C8 C9 C23 . . . . -124.8(2) ?
C17 C8 C9 C23 . . . . 57.4(3) ?
N2 C8 C9 C1 . . . . 65.6(3) ?
C17 C8 C9 C1 . . . . -112.1(2) ?
C1 N1 C10 C11 . . . . -133.9(2) ?
C2 N1 C10 C11 . . . . 63.9(3) ?
N1 C10 C11 C16 . . . . 15.8(4) ?
N1 C10 C11 C12 . . . . -168.0(2) ?
C16 C11 C12 C13 . . . . 1.3(4) ?
C10 C11 C12 C13 . . . . -175.1(3) ?
C11 C12 C13 C14 . . . . -1.6(5) ?
C12 C13 C14 C15 . . . . 0.6(5) ?
C13 C14 C15 C16 . . . . 0.8(6) ?
C12 C11 C16 C15 . . . . 0.1(4) ?
C10 C11 C16 C15 . . . . 176.3(3) ?
C14 C15 C16 C11 . . . . -1.1(5) ?
N2 C8 C17 C22 . . . . -161.3(2) ?
C9 C8 C17 C22 . . . . 16.6(3) ?
N2 C8 C17 C18 . . . . 19.5(3) ?
C9 C8 C17 C18 . . . . -162.6(2) ?
C22 C17 C18 C19 . . . . -0.7(4) ?
C8 C17 C18 C19 . . . . 178.5(2) ?
C17 C18 C19 C20 . . . . 0.2(5) ?
C18 C19 C20 C21 . . . . 0.9(6) ?
C19 C20 C21 C22 . . . . -1.6(6) ?
C18 C17 C22 C21 . . . . 0.1(4) ?
C8 C17 C22 C21 . . . . -179.1(3) ?
C20 C21 C22 C17 . . . . 1.1(5) ?
C24 N3 C23 C9 . . . . 6.3(4) ?
C25 N3 C23 C9 . . . . -178.8(2) ?
C1 C9 C23 N3 . . . . -174.8(2) ?
C8 C9 C23 N3 . . . . 15.9(4) ?
C27 N4 C26 C34 . . . . 22.1(3) ?
C35 N4 C26 C34 . . . . -166.9(2) ?
C27 N4 C26 S2 . . . . -160.33(17) ?
C35 N4 C26 S2 . . . . 10.6(3) ?
C26 N4 C27 C28 . . . . 124.0(2) ?
C35 N4 C27 C28 . . . . -47.4(3) ?
C26 N4 C27 C32 . . . . -57.5(3) ?
C35 N4 C27 C32 . . . . 131.1(2) ?
C32 C27 C28 C29 . . . . 0.3(3) ?
N4 C27 C28 C29 . . . . 178.9(2) ?
C27 C28 C29 C30 . . . . -1.2(4) ?
C28 C29 C30 C31 . . . . 0.5(4) ?
C29 C30 C31 C32 . . . . 1.0(4) ?
C33 N5 C32 C31 . . . . -134.9(2) ?
C33 N5 C32 C27 . . . . 46.8(3) ?
C30 C31 C32 N5 . . . . 179.7(2) ?
C30 C31 C32 C27 . . . . -1.8(3) ?
C28 C27 C32 N5 . . . . 179.5(2) ?
N4 C27 C32 N5 . . . . 1.0(3) ?
C28 C27 C32 C31 . . . . 1.1(3) ?
N4 C27 C32 C31 . . . . -177.4(2) ?
C32 N5 C33 C42 . . . . 175.4(2) ?
C32 N5 C33 C34 . . . . -7.2(3) ?
N4 C26 C34 C48 . . . . -142.3(2) ?
S2 C26 C34 C48 . . . . 40.1(3) ?
N4 C26 C34 C33 . . . . 51.5(3) ?
S2 C26 C34 C33 . . . . -126.0(2) ?
N5 C33 C34 C48 . . . . 132.1(3) ?
C42 C33 C34 C48 . . . . -50.5(3) ?
N5 C33 C34 C26 . . . . -62.9(3) ?
C42 C33 C34 C26 . . . . 114.5(2) ?
C26 N4 C35 C36 . . . . 97.5(3) ?
C27 N4 C35 C36 . . . . -91.2(3) ?
N4 C35 C36 C41 . . . . 11.7(4) ?
N4 C35 C36 C37 . . . . -170.6(2) ?
C41 C36 C37 C38 . . . . -1.7(4) ?
C35 C36 C37 C38 . . . . -179.5(3) ?
C36 C37 C38 C39 . . . . 2.1(5) ?
C37 C38 C39 C40 . . . . -0.9(6) ?
C38 C39 C40 C41 . . . . -0.5(6) ?
C37 C36 C41 C40 . . . . 0.2(4) ?
C35 C36 C41 C40 . . . . 177.9(3) ?
C39 C40 C41 C36 . . . . 0.9(5) ?
N5 C33 C42 C47 . . . . 159.0(2) ?
C34 C33 C42 C47 . . . . -18.6(3) ?
N5 C33 C42 C43 . . . . -22.7(3) ?
C34 C33 C42 C43 . . . . 159.7(2) ?
C47 C42 C43 C44 . . . . 0.3(4) ?
C33 C42 C43 C44 . . . . -178.0(3) ?
C42 C43 C44 C45 . . . . 0.5(5) ?
C43 C44 C45 C46 . . . . -1.2(6) ?
C44 C45 C46 C47 . . . . 1.0(6) ?
C43 C42 C47 C46 . . . . -0.6(4) ?
C33 C42 C47 C46 . . . . 177.8(3) ?
C45 C46 C47 C42 . . . . -0.1(5) ?
C49 N6 C48 C34 . . . . -6.0(4) ?
C50 N6 C48 C34 . . . . 172.6(3) ?
C26 C34 C48 N6 . . . . 175.5(2) ?
C33 C34 C48 N6 . . . . -20.0(4) ?
