#------------------------------------------------------------------------------
#$Date: 2023-07-05 02:03:06 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/33/7713372.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_7713372
loop_
_publ_author_name
'Arion, Vladimir'
'Wittmann, Christopher'
'Dömötör, Orsolya'
'Kuznetcova, Irina'
'Spengler, Gabriella'
'Reynisson, Johannes'
'Holder, Lauren'
'Miller, Gavin John'
'Enyedy, Eva A.'
'Bai, Ruoli'
'Hamel, Ernest'
_publ_section_title
;
 Indolo[2,3-e]benzazocines and indolo[2,3-f]benzazonines and their
 copper(II) complexes as microtubule destabilizing agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01632C
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 N2 S, 0.5(C H4 O)'
_chemical_formula_sum            'C17.5 H16 N2 O0.5 S'
_chemical_formula_weight         294.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                108.2046(11)
_cell_angle_beta                 100.2398(10)
_cell_angle_gamma                92.5769(7)
_cell_formula_units_Z            4
_cell_length_a                   9.1130(2)
_cell_length_b                   10.6532(2)
_cell_length_c                   16.7093(5)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      44.23
_cell_measurement_theta_min      2.62
_cell_volume                     1507.65(6)
_computing_cell_refinement       'SAINT v8.38A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.38A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36358
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.629
_diffrn_reflns_theta_min         2.284
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7492
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         13634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0385P)²+0.6907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11272
_reflns_number_total             13634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01632c2.cif
_cod_data_source_block           chwi360
_cod_original_formula_sum        'C17.50 H16 N2 O0.50 S'
_cod_database_code               7713372
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34068(11) -0.06690(10) 0.10988(6) 0.01709(16) Uani 1 1 d . . . . .
H1 H 0.3492 0.0193 0.1046 0.021 Uiso 1 1 calc R U . . .
C2 C 0.40034(12) -0.17010(12) 0.05533(7) 0.0231(2) Uani 1 1 d . . . . .
H2 H 0.4502 -0.1542 0.0135 0.028 Uiso 1 1 calc R U . . .
C3 C 0.38658(14) -0.29663(12) 0.06236(7) 0.0270(2) Uani 1 1 d . . . . .
H3 H 0.4274 -0.3674 0.0255 0.032 Uiso 1 1 calc R U . . .
C4 C 0.31316(13) -0.31925(11) 0.12329(7) 0.0237(2) Uani 1 1 d . . . . .
H4 H 0.3033 -0.4061 0.1274 0.028 Uiso 1 1 calc R U . . .
C4A C 0.25328(10) -0.21645(9) 0.17890(6) 0.01588(16) Uani 1 1 d . . . . .
C5 C 0.17596(11) -0.24422(10) 0.24509(7) 0.01824(17) Uani 1 1 d . . . . .
H5A H 0.1283 -0.3371 0.2224 0.022 Uiso 1 1 calc R U . . .
H5B H 0.0957 -0.1850 0.2551 0.022 Uiso 1 1 calc R U . . .
C6 C 0.28290(11) -0.22350(10) 0.33009(7) 0.01788(17) Uani 1 1 d . . . . .
H6A H 0.2270 -0.2544 0.3673 0.021 Uiso 1 1 calc R U . . .
H6B H 0.3632 -0.2822 0.3184 0.021 Uiso 1 1 calc R U . . .
N7 N 0.35529(9) -0.08801(8) 0.37967(5) 0.01594(14) Uani 1 1 d . . . . .
H7 H 0.4405 -0.0877 0.4141 0.019 Uiso 1 1 calc R U . . .
C8 C 0.32113(10) 0.03337(9) 0.38407(6) 0.01391(15) Uani 1 1 d . . . . .
S1 S 0.40902(3) 0.16643(2) 0.46862(2) 0.01800(5) Uani 1 1 d . . . . .
C8A C 0.21390(10) 0.06123(9) 0.31645(6) 0.01287(14) Uani 1 1 d . . . . .
N9 N 0.12696(9) 0.16438(8) 0.34052(5) 0.01647(14) Uani 1 1 d . . . . .
H9 H 0.1192 0.2072 0.3937 0.020 Uiso 1 1 calc R U . . .
C9A C 0.05489(10) 0.18956(9) 0.26895(6) 0.01525(15) Uani 1 1 d . . . . .
C10 C -0.05065(12) 0.27875(11) 0.26113(7) 0.02143(19) Uani 1 1 d . . . . .
H10 H -0.0821 0.3354 0.3099 0.026 Uiso 1 1 calc R U . . .
C11 C -0.10705(13) 0.28055(11) 0.17890(7) 0.0239(2) Uani 1 1 d . . . . .
H11 H -0.1800 0.3389 0.1712 0.029 Uiso 1 1 calc R U . . .
C12 C -0.05905(12) 0.19799(11) 0.10627(7) 0.02035(18) Uani 1 1 d . . . . .
H12 H -0.0982 0.2035 0.0510 0.024 Uiso 1 1 calc R U . . .
C13 C 0.04414(10) 0.10923(10) 0.11448(6) 0.01543(15) Uani 1 1 d . . . . .
H13 H 0.0759 0.0536 0.0655 0.019 Uiso 1 1 calc R U . . .
C13A C 0.10099(10) 0.10309(9) 0.19693(6) 0.01252(14) Uani 1 1 d . . . . .
C13B C 0.20007(10) 0.01965(8) 0.22760(5) 0.01174(14) Uani 1 1 d . . . . .
C13C C 0.26812(10) -0.08866(9) 0.17250(6) 0.01339(14) Uani 1 1 d . . . . .
C14 C -0.20857(12) 0.61083(10) 0.12547(6) 0.01909(17) Uani 1 1 d . . . . .
H14 H -0.2073 0.5202 0.1221 0.023 Uiso 1 1 calc R U . . .
C15 C -0.17021(13) 0.64946(12) 0.05916(7) 0.0249(2) Uani 1 1 d . . . . .
H15 H -0.1435 0.5861 0.0113 0.030 Uiso 1 1 calc R U . . .
C16 C -0.17138(14) 0.78197(13) 0.06364(7) 0.0265(2) Uani 1 1 d . . . . .
H16 H -0.1448 0.8101 0.0190 0.032 Uiso 1 1 calc R U . . .
C17 C -0.21154(12) 0.87224(11) 0.13371(7) 0.02189(19) Uani 1 1 d . . . . .
H17 H -0.2120 0.9625 0.1362 0.026 Uiso 1 1 calc R U . . .
C17A C -0.25167(10) 0.83582(10) 0.20140(6) 0.01638(16) Uani 1 1 d . . . . .
C18 C -0.30179(12) 0.94688(10) 0.26966(7) 0.02007(18) Uani 1 1 d . . . . .
H18A H -0.2398 1.0302 0.2775 0.024 Uiso 1 1 calc R U . . .
H18B H -0.4067 0.9580 0.2471 0.024 Uiso 1 1 calc R U . . .
C19 C -0.29462(11) 0.93199(9) 0.35735(6) 0.01718(16) Uani 1 1 d . . . . .
H19A H -0.3233 1.0140 0.3962 0.021 Uiso 1 1 calc R U . . .
H19B H -0.3688 0.8575 0.3520 0.021 Uiso 1 1 calc R U . . .
N20 N -0.14601(9) 0.90716(8) 0.39621(5) 0.01571(14) Uani 1 1 d . . . . .
H20 H -0.0743 0.9737 0.4151 0.019 Uiso 1 1 calc R U . . .
C21 C -0.11180(10) 0.79181(9) 0.40501(6) 0.01326(14) Uani 1 1 d . . . . .
S2 S 0.03660(3) 0.78106(2) 0.47892(2) 0.01507(5) Uani 1 1 d . . . . .
C21A C -0.21100(10) 0.67426(9) 0.34922(6) 0.01309(14) Uani 1 1 d . . . . .
N22 N -0.24865(9) 0.57535(8) 0.38135(5) 0.01428(13) Uani 1 1 d . . . . .
H22 H -0.2140 0.5736 0.4336 0.017 Uiso 1 1 calc R U . . .
C22A C -0.34883(10) 0.48039(9) 0.31845(6) 0.01376(15) Uani 1 1 d . . . . .
C23 C -0.42192(11) 0.36399(10) 0.32216(7) 0.01817(17) Uani 1 1 d . . . . .
H23 H -0.4044 0.3400 0.3730 0.022 Uiso 1 1 calc R U . . .
C24 C -0.52040(12) 0.28596(10) 0.24863(7) 0.02152(19) Uani 1 1 d . . . . .
H24 H -0.5722 0.2068 0.2490 0.026 Uiso 1 1 calc R U . . .
C25 C -0.54590(12) 0.32105(10) 0.17290(7) 0.02002(18) Uani 1 1 d . . . . .
H25 H -0.6150 0.2654 0.1236 0.024 Uiso 1 1 calc R U . . .
C26 C -0.47239(11) 0.43481(9) 0.16896(6) 0.01583(15) Uani 1 1 d . . . . .
H26 H -0.4891 0.4568 0.1174 0.019 Uiso 1 1 calc R U . . .
C26A C -0.37179(10) 0.51766(9) 0.24334(6) 0.01313(14) Uani 1 1 d . . . . .
C26B C -0.28202(10) 0.64240(9) 0.26324(6) 0.01309(14) Uani 1 1 d . . . . .
C26C C -0.24937(10) 0.70180(9) 0.19774(6) 0.01447(15) Uani 1 1 d . . . . .
O1 O -0.15633(9) 0.51844(8) 0.53839(5) 0.02291(15) Uani 1 1 d . . . . .
H100 H -0.1080 0.4498 0.5352 0.027 Uiso 1 1 d R U . . .
C27 C -0.27684(15) 0.50848(12) 0.58107(8) 0.0279(2) Uani 1 1 d . . . . .
H27A H -0.3360 0.4217 0.5525 0.042 Uiso 1 1 calc R U . . .
H27B H -0.3410 0.5791 0.5787 0.042 Uiso 1 1 calc R U . . .
H27C H -0.2362 0.5177 0.6412 0.042 Uiso 1 1 calc R U . . .
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'
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
C2 C1 C13C 120.79(10) . . ?
C2 C1 H1 119.6 . . ?
C13C C1 H1 119.6 . . ?
C3 C2 C1 119.64(10) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.86(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C4A 121.19(10) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C13C 119.09(10) . . ?
C4 C4A C5 119.77(9) . . ?
C13C C4A C5 121.14(8) . . ?
C4A C5 C6 112.61(8) . . ?
C4A C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4A C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N7 C6 C5 118.23(8) . . ?
N7 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
N7 C6 H6B 107.8 . . ?
C5 C6 H6B 107.8 . . ?
H6A C6 H6B 107.1 . . ?
C8 N7 C6 134.55(8) . . ?
C8 N7 H7 112.7 . . ?
C6 N7 H7 112.7 . . ?
N7 C8 C8A 123.12(8) . . ?
N7 C8 S1 119.93(7) . . ?
C8A C8 S1 116.89(7) . . ?
N9 C8A C13B 109.07(8) . . ?
N9 C8A C8 118.36(8) . . ?
C13B C8A C8 131.30(8) . . ?
C9A N9 C8A 109.51(7) . . ?
C9A N9 H9 125.2 . . ?
C8A N9 H9 125.2 . . ?
N9 C9A C10 129.92(9) . . ?
N9 C9A C13A 107.77(8) . . ?
C10 C9A C13A 122.28(9) . . ?
C11 C10 C9A 116.88(9) . . ?
C11 C10 H10 121.6 . . ?
C9A C10 H10 121.6 . . ?
C10 C11 C12 121.80(9) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 120.93(9) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C13A 118.57(9) . . ?
C12 C13 H13 120.7 . . ?
C13A C13 H13 120.7 . . ?
C13 C13A C9A 119.49(8) . . ?
C13 C13A C13B 133.15(8) . . ?
C9A C13A C13B 107.32(8) . . ?
C8A C13B C13A 106.28(7) . . ?
C8A C13B C13C 128.92(8) . . ?
C13A C13B C13C 124.80(8) . . ?
C4A C13C C1 119.41(8) . . ?
C4A C13C C13B 120.05(8) . . ?
C1 C13C C13B 120.44(8) . . ?
C15 C14 C26C 122.19(10) . . ?
C15 C14 H14 118.9 . . ?
C26C C14 H14 118.9 . . ?
C14 C15 C16 119.27(10) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.32(10) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C17A 122.62(10) . . ?
C16 C17 H17 118.7 . . ?
C17A C17 H17 118.7 . . ?
C17 C17A C26C 118.41(9) . . ?
C17 C17A C18 114.87(9) . . ?
C26C C17A C18 126.63(9) . . ?
C19 C18 C17A 117.73(8) . . ?
C19 C18 H18A 107.9 . . ?
C17A C18 H18A 107.9 . . ?
C19 C18 H18B 107.9 . . ?
C17A C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
N20 C19 C18 113.51(8) . . ?
N20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 N20 C19 124.82(8) . . ?
C21 N20 H20 117.6 . . ?
C19 N20 H20 117.6 . . ?
N20 C21 C21A 116.49(8) . . ?
N20 C21 S2 122.11(7) . . ?
C21A C21 S2 121.37(7) . . ?
N22 C21A C26B 110.37(8) . . ?
N22 C21A C21 119.83(8) . . ?
C26B C21A C21 129.80(8) . . ?
C22A N22 C21A 108.63(8) . . ?
C22A N22 H22 125.7 . . ?
C21A N22 H22 125.7 . . ?
N22 C22A C23 129.16(9) . . ?
N22 C22A C26A 108.24(8) . . ?
C23 C22A C26A 122.60(8) . . ?
C24 C23 C22A 117.02(9) . . ?
C24 C23 H23 121.5 . . ?
C22A C23 H23 121.5 . . ?
C23 C24 C25 121.57(9) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C26 C25 C24 121.37(9) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C26A 118.56(9) . . ?
C25 C26 H26 120.7 . . ?
C26A C26 H26 120.7 . . ?
C26 C26A C22A 118.88(8) . . ?
C26 C26A C26B 133.64(9) . . ?
C22A C26A C26B 107.46(8) . . ?
C21A C26B C26A 105.25(8) . . ?
C21A C26B C26C 128.98(8) . . ?
C26A C26B C26C 124.31(8) . . ?
C17A C26C C14 118.18(9) . . ?
C17A C26C C26B 127.54(8) . . ?
C14 C26C C26B 114.27(8) . . ?
C27 O1 H100 108.1 . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
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
C1 C2 1.3924(14) . ?
C1 C13C 1.4034(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.3913(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3867(18) . ?
C3 H3 0.9500 . ?
C4 C4A 1.3995(14) . ?
C4 H4 0.9500 . ?
C4A C13C 1.4009(13) . ?
C4A C5 1.5066(14) . ?
C5 C6 1.5193(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.4758(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.3264(12) . ?
N7 H7 0.8800 . ?
C8 C8A 1.4706(12) . ?
C8 S1 1.7004(10) . ?
C8A N9 1.3830(11) . ?
C8A C13B 1.3906(12) . ?
N9 C9A 1.3676(12) . ?
N9 H9 0.8800 . ?
C9A C10 1.4000(13) . ?
C9A C13A 1.4125(12) . ?
C10 C11 1.3850(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4122(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3829(14) . ?
C12 H12 0.9500 . ?
C13 C13A 1.4057(13) . ?
C13 H13 0.9500 . ?
C13A C13B 1.4354(12) . ?
C13B C13C 1.4722(12) . ?
C14 C15 1.3889(15) . ?
C14 C26C 1.4130(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.3906(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3820(17) . ?
C16 H16 0.9500 . ?
C17 C17A 1.4043(14) . ?
C17 H17 0.9500 . ?
C17A C26C 1.4111(13) . ?
C17A C18 1.5165(15) . ?
C18 C19 1.5128(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N20 1.4671(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C21 1.3266(12) . ?
N20 H20 0.8800 . ?
C21 C21A 1.4572(12) . ?
C21 S2 1.6958(9) . ?
C21A N22 1.3794(12) . ?
C21A C26B 1.3940(13) . ?
N22 C22A 1.3685(12) . ?
N22 H22 0.8800 . ?
C22A C23 1.4049(13) . ?
C22A C26A 1.4148(13) . ?
C23 C24 1.3816(14) . ?
C23 H23 0.9500 . ?
C24 C25 1.4119(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3836(14) . ?
C25 H25 0.9500 . ?
C26 C26A 1.4145(13) . ?
C26 H26 0.9500 . ?
C26A C26B 1.4405(12) . ?
C26B C26C 1.4895(13) . ?
O1 C27 1.4287(14) . ?
O1 H100 0.8629 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A S2 0.99 2.72 3.6255(10) 152.2 1_545
N7 H7 S1 0.88 2.57 3.3595(8) 150.0 2_656
N9 H9 S2 0.88 2.74 3.4990(9) 145.8 2_566
C19 H19B N7 0.99 2.69 3.2824(13) 118.5 1_465
N20 H20 S2 0.88 2.63 3.3184(8) 136.4 2_576
N22 H22 O1 0.88 2.01 2.8665(11) 164.7 .
O1 H100 S2 0.86 2.52 3.3620(8) 164.5 2_566
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
C13C C1 C2 C3 0.65(15) . . . . ?
C1 C2 C3 C4 0.27(17) . . . . ?
C2 C3 C4 C4A -0.62(17) . . . . ?
C3 C4 C4A C13C 0.04(16) . . . . ?
C3 C4 C4A C5 -179.21(10) . . . . ?
C4 C4A C5 C6 90.27(11) . . . . ?
C13C C4A C5 C6 -88.97(11) . . . . ?
C4A C5 C6 N7 64.68(11) . . . . ?
C5 C6 N7 C8 24.77(16) . . . . ?
C6 N7 C8 C8A -19.59(16) . . . . ?
C6 N7 C8 S1 163.37(9) . . . . ?
N7 C8 C8A N9 146.51(9) . . . . ?
S1 C8 C8A N9 -36.36(11) . . . . ?
N7 C8 C8A C13B -47.96(15) . . . . ?
S1 C8 C8A C13B 129.16(9) . . . . ?
C13B C8A N9 C9A 0.91(11) . . . . ?
C8 C8A N9 C9A 169.45(8) . . . . ?
C8A N9 C9A C10 175.83(11) . . . . ?
C8A N9 C9A C13A -2.09(11) . . . . ?
N9 C9A C10 C11 -178.75(11) . . . . ?
C13A C9A C10 C11 -1.09(16) . . . . ?
C9A C10 C11 C12 -0.95(18) . . . . ?
C10 C11 C12 C13 1.64(18) . . . . ?
C11 C12 C13 C13A -0.23(15) . . . . ?
C12 C13 C13A C9A -1.75(14) . . . . ?
C12 C13 C13A C13B 175.84(10) . . . . ?
N9 C9A C13A C13 -179.41(8) . . . . ?
C10 C9A C13A C13 2.47(15) . . . . ?
N9 C9A C13A C13B 2.44(10) . . . . ?
C10 C9A C13A C13B -175.68(9) . . . . ?
N9 C8A C13B C13A 0.62(10) . . . . ?
C8 C8A C13B C13A -165.92(9) . . . . ?
N9 C8A C13B C13C -178.37(9) . . . . ?
C8 C8A C13B C13C 15.09(16) . . . . ?
C13 C13A C13B C8A -179.66(10) . . . . ?
C9A C13A C13B C8A -1.87(10) . . . . ?
C13 C13A C13B C13C -0.62(16) . . . . ?
C9A C13A C13B C13C 177.17(8) . . . . ?
C4 C4A C13C C1 0.86(14) . . . . ?
C5 C4A C13C C1 -179.89(9) . . . . ?
C4 C4A C13C C13B 177.21(9) . . . . ?
C5 C4A C13C C13B -3.55(13) . . . . ?
C2 C1 C13C C4A -1.22(14) . . . . ?
C2 C1 C13C C13B -177.54(9) . . . . ?
C8A C13B C13C C4A 51.78(13) . . . . ?
C13A C13B C13C C4A -127.03(10) . . . . ?
C8A C13B C13C C1 -131.92(10) . . . . ?
C13A C13B C13C C1 49.27(13) . . . . ?
C26C C14 C15 C16 0.15(17) . . . . ?
C14 C15 C16 C17 -0.39(17) . . . . ?
C15 C16 C17 C17A 0.02(17) . . . . ?
C16 C17 C17A C26C 0.59(15) . . . . ?
C16 C17 C17A C18 -176.26(10) . . . . ?
C17 C17A C18 C19 -159.08(9) . . . . ?
C26C C17A C18 C19 24.38(14) . . . . ?
C17A C18 C19 N20 54.49(12) . . . . ?
C18 C19 N20 C21 -107.99(11) . . . . ?
C19 N20 C21 C21A 20.47(13) . . . . ?
C19 N20 C21 S2 -157.94(8) . . . . ?
N20 C21 C21A N22 -140.12(9) . . . . ?
S2 C21 C21A N22 38.30(11) . . . . ?
N20 C21 C21A C26B 38.55(14) . . . . ?
S2 C21 C21A C26B -143.02(9) . . . . ?
C26B C21A N22 C22A -2.37(10) . . . . ?
C21 C21A N22 C22A 176.55(8) . . . . ?
C21A N22 C22A C23 -177.74(9) . . . . ?
C21A N22 C22A C26A 1.97(10) . . . . ?
N22 C22A C23 C24 179.02(10) . . . . ?
C26A C22A C23 C24 -0.65(14) . . . . ?
C22A C23 C24 C25 0.38(16) . . . . ?
C23 C24 C25 C26 0.46(17) . . . . ?
C24 C25 C26 C26A -1.02(15) . . . . ?
C25 C26 C26A C22A 0.73(13) . . . . ?
C25 C26 C26A C26B -177.63(10) . . . . ?
N22 C22A C26A C26 -179.63(8) . . . . ?
C23 C22A C26A C26 0.10(14) . . . . ?
N22 C22A C26A C26B -0.88(10) . . . . ?
C23 C22A C26A C26B 178.86(9) . . . . ?
N22 C21A C26B C26A 1.75(10) . . . . ?
C21 C21A C26B C26A -177.02(9) . . . . ?
N22 C21A C26B C26C -164.72(9) . . . . ?
C21 C21A C26B C26C 16.51(16) . . . . ?
C26 C26A C26B C21A 177.97(10) . . . . ?
C22A C26A C26B C21A -0.52(10) . . . . ?
C26 C26A C26B C26C -14.75(16) . . . . ?
C22A C26A C26B C26C 166.76(8) . . . . ?
C17 C17A C26C C14 -0.80(13) . . . . ?
C18 C17A C26C C14 175.64(9) . . . . ?
C17 C17A C26C C26B 177.62(9) . . . . ?
C18 C17A C26C C26B -5.94(15) . . . . ?
C15 C14 C26C C17A 0.45(15) . . . . ?
C15 C14 C26C C26B -178.18(10) . . . . ?
C21A C26B C26C C17A -59.11(15) . . . . ?
C26A C26B C26C C17A 136.75(10) . . . . ?
C21A C26B C26C C14 119.36(11) . . . . ?
C26A C26B C26C C14 -44.78(13) . . . . ?
