#------------------------------------------------------------------------------
#$Date: 2022-01-20 00:49:15 +0200 (Thu, 20 Jan 2022) $
#$Revision: 272138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129594.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_7129594
loop_
_publ_author_name
Gayyur,
'Choudhary, Shivani'
'Kant, Ruchir'
'Ghosh, Nayan'
_publ_section_title
;
 Synergetic copper/zinc catalysis: synthesis of aryl/heteroaryl-fused
 1H-pyrrolo[3,2-c]pyridines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05514C
_journal_year                    2022
_chemical_formula_sum            'C27 H26 N4 O4 S2'
_chemical_formula_weight         534.64
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-08-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.4110(10)
_cell_angle_beta                 91.3210(10)
_cell_angle_gamma                97.8180(10)
_cell_formula_units_Z            4
_cell_length_a                   11.8340(3)
_cell_length_b                   13.5204(3)
_cell_length_c                   16.9352(4)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.41
_cell_volume                     2683.59(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45794
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.9191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         2.345
_refine_diff_density_min         -1.607
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         13378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0695
_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)+(0.0991P)²+5.9086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.1967
_reflns_number_gt                10771
_reflns_number_total             13378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05514c2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129594
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9811(3) 0.2302(2) 0.2578(2) 0.0339(8) Uani 1 1 d . . .
H1 H 0.9160 0.2445 0.2829 0.041 Uiso 1 1 calc R . .
C2 C 0.9829(5) 0.1356(3) 0.2245(3) 0.0519(12) Uani 1 1 d . . .
H2 H 0.9209 0.0860 0.2293 0.062 Uiso 1 1 calc R . .
C3 C 1.0793(5) 0.1166(4) 0.1837(4) 0.0763(19) Uani 1 1 d . . .
H3 H 1.0823 0.0533 0.1626 0.092 Uiso 1 1 calc R . .
C4 C 1.1702(5) 0.1912(5) 0.1744(5) 0.092(2) Uani 1 1 d . . .
H4 H 1.2319 0.1798 0.1442 0.111 Uiso 1 1 calc R . .
C5 C 1.1682(4) 0.2834(4) 0.2108(4) 0.0668(17) Uani 1 1 d . . .
H5 H 1.2301 0.3331 0.2063 0.080 Uiso 1 1 calc R . .
C6 C 1.0740(3) 0.3020(2) 0.25401(18) 0.0230(6) Uani 1 1 d . . .
C7 C 1.0803(2) 0.4015(2) 0.29572(17) 0.0179(5) Uani 1 1 d . . .
H7A H 1.0957 0.3927 0.3516 0.021 Uiso 1 1 calc R . .
H7B H 1.1434 0.4466 0.2752 0.021 Uiso 1 1 calc R . .
C8 C 1.0381(2) 0.60733(19) 0.38542(17) 0.0181(5) Uani 1 1 d . . .
H8A H 1.0184 0.6414 0.4320 0.027 Uiso 1 1 calc R . .
H8B H 1.0403 0.6517 0.3413 0.027 Uiso 1 1 calc R . .
H8C H 1.1117 0.5861 0.3933 0.027 Uiso 1 1 calc R . .
C9 C 0.9593(2) 0.49652(19) 0.21164(15) 0.0142(5) Uani 1 1 d . . .
C10 C 1.0405(2) 0.5877(2) 0.10744(16) 0.0170(5) Uani 1 1 d . . .
C11 C 1.1402(3) 0.6391(2) 0.07476(18) 0.0223(6) Uani 1 1 d . . .
H11 H 1.2094 0.6422 0.1024 0.027 Uiso 1 1 calc R . .
C12 C 1.1364(3) 0.6846(2) 0.00276(18) 0.0254(6) Uani 1 1 d . . .
H12 H 1.2026 0.7191 -0.0175 0.031 Uiso 1 1 calc R . .
C13 C 1.0326(3) 0.6790(2) -0.04054(18) 0.0263(6) Uani 1 1 d . . .
H13 H 1.0307 0.7099 -0.0894 0.032 Uiso 1 1 calc R . .
C14 C 0.9342(3) 0.6284(2) -0.01111(17) 0.0227(6) Uani 1 1 d . . .
H14 H 0.8663 0.6243 -0.0404 0.027 Uiso 1 1 calc R . .
C15 C 0.9358(2) 0.5825(2) 0.06366(16) 0.0172(5) Uani 1 1 d . . .
C16 C 0.8400(2) 0.5299(2) 0.10076(16) 0.0164(5) Uani 1 1 d . . .
C17 C 0.6677(2) 0.4580(2) 0.13397(16) 0.0164(5) Uani 1 1 d . . .
C18 C 0.7384(2) 0.4412(2) 0.19567(16) 0.0158(5) Uani 1 1 d . . .
H18 H 0.7183 0.4070 0.2418 0.019 Uiso 1 1 calc R . .
C19 C 0.8492(2) 0.48689(19) 0.17508(15) 0.0151(5) Uani 1 1 d . . .
C20 C 0.4469(3) 0.5547(3) 0.21227(18) 0.0310(7) Uani 1 1 d . . .
H20A H 0.5205 0.5822 0.2334 0.046 Uiso 1 1 calc R . .
H20B H 0.4145 0.5011 0.2451 0.046 Uiso 1 1 calc R . .
H20C H 0.3977 0.6056 0.2108 0.046 Uiso 1 1 calc R . .
C21 C 0.5067(2) 0.3277(2) 0.15989(17) 0.0216(6) Uani 1 1 d . . .
H21A H 0.4240 0.3166 0.1560 0.026 Uiso 1 1 calc R . .
H21B H 0.5290 0.3303 0.2154 0.026 Uiso 1 1 calc R . .
C22 C 0.5538(2) 0.2432(2) 0.12034(18) 0.0222(6) Uani 1 1 d . . .
C23 C 0.5212(3) 0.2173(2) 0.0423(2) 0.0288(7) Uani 1 1 d . . .
H23 H 0.4716 0.2534 0.0151 0.035 Uiso 1 1 calc R . .
C24 C 0.5623(4) 0.1381(3) 0.0052(2) 0.0375(8) Uani 1 1 d . . .
H24 H 0.5397 0.1214 -0.0467 0.045 Uiso 1 1 calc R . .
C25 C 0.6363(4) 0.0842(3) 0.0445(3) 0.0418(9) Uani 1 1 d . . .
H25 H 0.6635 0.0312 0.0193 0.050 Uiso 1 1 calc R . .
C26 C 0.6700(3) 0.1090(3) 0.1214(3) 0.0411(9) Uani 1 1 d . . .
H26 H 0.7204 0.0730 0.1479 0.049 Uiso 1 1 calc R . .
C27 C 0.6286(3) 0.1884(3) 0.1595(2) 0.0318(7) Uani 1 1 d . . .
H27 H 0.6512 0.2047 0.2115 0.038 Uiso 1 1 calc R . .
C28 C 0.3746(3) 0.9680(2) 0.32649(19) 0.0251(6) Uani 1 1 d . . .
H28 H 0.4033 0.9919 0.3756 0.030 Uiso 1 1 calc R . .
C29 C 0.4070(3) 1.0207(3) 0.2585(2) 0.0367(8) Uani 1 1 d . . .
H29 H 0.4580 1.0794 0.2624 0.044 Uiso 1 1 calc R . .
C30 C 0.3640(4) 0.9866(3) 0.1853(2) 0.0426(9) Uani 1 1 d . . .
H30 H 0.3856 1.0226 0.1402 0.051 Uiso 1 1 calc R . .
C31 C 0.2891(4) 0.8991(3) 0.1789(2) 0.0407(9) Uani 1 1 d . . .
H31 H 0.2599 0.8761 0.1297 0.049 Uiso 1 1 calc R . .
C32 C 0.2576(3) 0.8452(3) 0.2470(2) 0.0300(7) Uani 1 1 d . . .
H32 H 0.2081 0.7856 0.2427 0.036 Uiso 1 1 calc R . .
C33 C 0.2992(2) 0.8795(2) 0.32088(18) 0.0198(5) Uani 1 1 d . . .
C34 C 0.2590(2) 0.8247(2) 0.39452(18) 0.0192(5) Uani 1 1 d . . .
H34A H 0.2050 0.8609 0.4207 0.023 Uiso 1 1 calc R . .
H34B H 0.2199 0.7591 0.3800 0.023 Uiso 1 1 calc R . .
C35 C 0.2407(3) 0.7637(2) 0.5841(2) 0.0256(6) Uani 1 1 d . . .
H35A H 0.2379 0.7778 0.6397 0.038 Uiso 1 1 calc R . .
H35B H 0.2599 0.6976 0.5766 0.038 Uiso 1 1 calc R . .
H35C H 0.1676 0.7681 0.5597 0.038 Uiso 1 1 calc R . .
C36 C 0.4097(2) 0.72543(19) 0.43823(15) 0.0134(5) Uani 1 1 d . . .
C37 C 0.3928(2) 0.55483(18) 0.41795(15) 0.0134(5) Uani 1 1 d . . .
C38 C 0.3215(2) 0.46220(19) 0.41551(16) 0.0166(5) Uani 1 1 d . . .
H38 H 0.2443 0.4599 0.4259 0.020 Uiso 1 1 calc R . .
C39 C 0.3643(2) 0.37548(19) 0.39798(17) 0.0181(5) Uani 1 1 d . . .
H39 H 0.3158 0.3153 0.3954 0.022 Uiso 1 1 calc R . .
C40 C 0.4812(2) 0.37713(19) 0.38385(16) 0.0171(5) Uani 1 1 d . . .
H40 H 0.5093 0.3181 0.3714 0.021 Uiso 1 1 calc R . .
C41 C 0.5542(2) 0.46518(19) 0.38822(15) 0.0145(5) Uani 1 1 d . . .
H41 H 0.6316 0.4655 0.3799 0.017 Uiso 1 1 calc R . .
C42 C 0.5113(2) 0.55540(18) 0.40536(15) 0.0124(5) Uani 1 1 d . . .
C43 C 0.5786(2) 0.65090(19) 0.41297(16) 0.0145(5) Uani 1 1 d . . .
C44 C 0.7171(2) 0.7784(2) 0.42369(18) 0.0194(6) Uani 1 1 d . . .
C45 C 0.6192(2) 0.81792(19) 0.43827(18) 0.0191(5) Uani 1 1 d . . .
H45 H 0.6125 0.8840 0.4504 0.023 Uiso 1 1 calc R . .
C46 C 0.5294(2) 0.73641(19) 0.43092(16) 0.0151(5) Uani 1 1 d . . .
C47 C 0.8486(3) 0.9061(2) 0.5707(2) 0.0263(6) Uani 1 1 d . . .
H47A H 0.7692 0.8827 0.5777 0.039 Uiso 1 1 calc R . .
H47B H 0.8568 0.9724 0.5497 0.039 Uiso 1 1 calc R . .
H47C H 0.8886 0.9070 0.6207 0.039 Uiso 1 1 calc R . .
C48 C 0.8551(3) 0.9097(2) 0.36489(19) 0.0230(6) Uani 1 1 d . . .
H48A H 0.8127 0.9631 0.3802 0.028 Uiso 1 1 calc R . .
H48B H 0.9357 0.9355 0.3667 0.028 Uiso 1 1 calc R . .
C49 C 0.8202(5) 0.8747(3) 0.2839(3) 0.0502(12) Uani 1 1 d . . .
C50 C 0.9003(13) 0.8329(8) 0.2397(4) 0.211(8) Uani 1 1 d . . .
H50 H 0.9636 0.8163 0.2675 0.253 Uiso 1 1 calc R . .
C51 C 0.8962(11) 0.8121(5) 0.1542(5) 0.148(5) Uani 1 1 d . . .
H51 H 0.9548 0.8159 0.1182 0.178 Uiso 1 1 calc R . .
C52 C 0.7793(12) 0.7852(12) 0.1429(14) 0.353(17) Uani 1 1 d . . .
H52 H 0.7603 0.7278 0.1122 0.424 Uiso 1 1 calc R . .
C53 C 0.6951(9) 0.8222(7) 0.1655(4) 0.122(3) Uani 1 1 d . . .
H53 H 0.6264 0.8166 0.1369 0.146 Uiso 1 1 calc R . .
C54 C 0.7162(6) 0.8824(6) 0.2508(4) 0.109(3) Uani 1 1 d . . .
H54 H 0.6629 0.9177 0.2736 0.130 Uiso 1 1 calc R . .
H1A H 0.743(3) 0.642(3) 0.396(2) 0.030(10) Uiso 1 1 d . . .
H1B H 0.699(3) 0.529(3) 0.028(2) 0.026(9) Uiso 1 1 d . . .
N1 N 0.97374(19) 0.44734(16) 0.28603(13) 0.0144(4) Uani 1 1 d . . .
N2 N 1.0505(2) 0.54456(17) 0.18069(14) 0.0171(4) Uani 1 1 d . . .
N3 N 0.7285(2) 0.51034(18) 0.07556(14) 0.0180(5) Uani 1 1 d . . .
N4 N 0.54955(19) 0.42425(18) 0.12256(14) 0.0181(5) Uani 1 1 d . . .
N5 N 0.35522(19) 0.81360(16) 0.44983(14) 0.0157(4) Uani 1 1 d . . .
N6 N 0.34360(19) 0.63986(16) 0.43283(13) 0.0144(4) Uani 1 1 d . . .
N7 N 0.69284(19) 0.67744(16) 0.40723(15) 0.0167(5) Uani 1 1 d . . .
N8 N 0.8322(2) 0.82470(17) 0.42077(16) 0.0208(5) Uani 1 1 d . . .
O1 O 0.93743(19) 0.43341(15) 0.42953(12) 0.0235(4) Uani 1 1 d . . .
O2 O 0.82952(16) 0.53859(16) 0.34633(12) 0.0204(4) Uani 1 1 d . . .
O3 O 0.51568(19) 0.58876(17) 0.07002(13) 0.0256(5) Uani 1 1 d . . .
O4 O 0.35296(18) 0.45690(19) 0.08977(13) 0.0282(5) Uani 1 1 d . . .
O5 O 0.45253(18) 0.84535(15) 0.58026(13) 0.0222(4) Uani 1 1 d . . .
O6 O 0.30250(19) 0.94544(15) 0.53741(14) 0.0260(5) Uani 1 1 d . . .
O7 O 1.02068(17) 0.86851(16) 0.48768(15) 0.0275(5) Uani 1 1 d . . .
O8 O 0.88573(18) 0.72672(15) 0.53499(14) 0.0258(5) Uani 1 1 d . . .
S1 S 0.93537(5) 0.50248(5) 0.36633(4) 0.01368(14) Uani 1 1 d . . .
S2 S 0.46136(6) 0.50900(6) 0.11599(4) 0.02063(16) Uani 1 1 d . . .
S3 S 0.34493(6) 0.85109(5) 0.54096(4) 0.01732(15) Uani 1 1 d . . .
S4 S 0.90588(6) 0.82606(5) 0.50482(5) 0.02042(16) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C6 C1 C2 120.7(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 117.9(3) . . ?
N1 C7 C6 112.8(2) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C19 123.8(2) . . ?
N2 C9 N1 117.2(2) . . ?
C19 C9 N1 118.9(2) . . ?
N2 C10 C11 117.8(2) . . ?
N2 C10 C15 123.5(2) . . ?
C11 C10 C15 118.7(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 125.5(3) . . ?
C14 C15 C10 119.4(3) . . ?
C16 C15 C10 115.1(2) . . ?
N3 C16 C19 107.9(2) . . ?
N3 C16 C15 130.4(2) . . ?
C19 C16 C15 121.7(2) . . ?
C18 C17 N3 110.4(2) . . ?
C18 C17 N4 129.1(2) . . ?
N3 C17 N4 120.4(2) . . ?
C17 C18 C19 105.9(2) . . ?
C17 C18 H18 127.0 . . ?
C19 C18 H18 127.0 . . ?
C16 C19 C9 117.2(2) . . ?
C16 C19 C18 107.7(2) . . ?
C9 C19 C18 135.1(2) . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 C22 110.8(2) . . ?
N4 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 C21 121.7(3) . . ?
C23 C22 C21 119.7(3) . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 120.1(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.5(3) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C33 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C33 C28 H28 120.0 . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 119.5(4) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 120.8(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C28 119.1(3) . . ?
C32 C33 C34 120.6(3) . . ?
C28 C33 C34 120.3(3) . . ?
N5 C34 C33 111.7(2) . . ?
N5 C34 H34A 109.3 . . ?
C33 C34 H34A 109.3 . . ?
N5 C34 H34B 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
S3 C35 H35A 109.5 . . ?
S3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
S3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N6 C36 C46 123.9(2) . . ?
N6 C36 N5 117.2(2) . . ?
C46 C36 N5 118.9(2) . . ?
N6 C37 C38 118.1(2) . . ?
N6 C37 C42 123.7(2) . . ?
C38 C37 C42 118.2(2) . . ?
C39 C38 C37 120.9(3) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 120.4(2) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 120.5(2) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 119.9(2) . . ?
C40 C41 H41 120.1 . . ?
C42 C41 H41 120.1 . . ?
C41 C42 C37 120.0(2) . . ?
C41 C42 C43 125.1(2) . . ?
C37 C42 C43 114.9(2) . . ?
N7 C43 C46 108.3(2) . . ?
N7 C43 C42 130.2(2) . . ?
C46 C43 C42 121.4(2) . . ?
C45 C44 N7 110.5(2) . . ?
C45 C44 N8 130.6(2) . . ?
N7 C44 N8 118.8(2) . . ?
C44 C45 C46 105.5(2) . . ?
C44 C45 H45 127.3 . . ?
C46 C45 H45 127.3 . . ?
C43 C46 C36 117.5(2) . . ?
C43 C46 C45 107.6(2) . . ?
C36 C46 C45 134.8(2) . . ?
S4 C47 H47A 109.5 . . ?
S4 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
S4 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C49 C48 N8 109.4(3) . . ?
C49 C48 H48A 109.8 . . ?
N8 C48 H48A 109.8 . . ?
C49 C48 H48B 109.8 . . ?
N8 C48 H48B 109.8 . . ?
H48A C48 H48B 108.2 . . ?
C54 C49 C50 119.2(7) . . ?
C54 C49 C48 123.5(6) . . ?
C50 C49 C48 117.3(5) . . ?
C49 C50 C51 127.6(9) . . ?
C49 C50 H50 116.2 . . ?
C51 C50 H50 116.2 . . ?
C52 C51 C50 99.6(12) . . ?
C52 C51 H51 130.2 . . ?
C50 C51 H51 130.2 . . ?
C53 C52 C51 133.1(9) . . ?
C53 C52 H52 113.5 . . ?
C51 C52 H52 113.5 . . ?
C52 C53 C54 113.8(9) . . ?
C52 C53 H53 123.1 . . ?
C54 C53 H53 123.1 . . ?
C49 C54 C53 112.4(8) . . ?
C49 C54 H54 123.8 . . ?
C53 C54 H54 123.8 . . ?
C9 N1 C7 115.7(2) . . ?
C9 N1 S1 117.19(17) . . ?
C7 N1 S1 114.37(17) . . ?
C9 N2 C10 118.6(2) . . ?
C16 N3 C17 108.1(2) . . ?
C16 N3 H1B 126(2) . . ?
C17 N3 H1B 126(2) . . ?
C17 N4 C21 115.9(2) . . ?
C17 N4 S2 118.08(19) . . ?
C21 N4 S2 117.51(19) . . ?
C36 N5 C34 115.6(2) . . ?
C36 N5 S3 116.68(18) . . ?
C34 N5 S3 117.31(18) . . ?
C36 N6 C37 118.5(2) . . ?
C43 N7 C44 108.0(2) . . ?
C43 N7 H1A 129(3) . . ?
C44 N7 H1A 123(3) . . ?
C44 N8 C48 116.1(2) . . ?
C44 N8 S4 115.3(2) . . ?
C48 N8 S4 119.9(2) . . ?
O1 S1 O2 118.64(13) . . ?
O1 S1 N1 107.35(12) . . ?
O2 S1 N1 106.21(11) . . ?
O1 S1 C8 109.47(13) . . ?
O2 S1 C8 107.42(13) . . ?
N1 S1 C8 107.21(13) . . ?
O3 S2 O4 119.46(13) . . ?
O3 S2 N4 107.14(13) . . ?
O4 S2 N4 106.38(14) . . ?
O3 S2 C20 108.10(16) . . ?
O4 S2 C20 108.24(16) . . ?
N4 S2 C20 106.88(14) . . ?
O6 S3 O5 119.11(13) . . ?
O6 S3 N5 106.73(13) . . ?
O5 S3 N5 107.35(12) . . ?
O6 S3 C35 108.41(14) . . ?
O5 S3 C35 108.36(15) . . ?
N5 S3 C35 106.17(14) . . ?
O8 S4 O7 119.02(13) . . ?
O8 S4 N8 106.36(13) . . ?
O7 S4 N8 106.30(14) . . ?
O8 S4 C47 108.28(15) . . ?
O7 S4 C47 108.74(14) . . ?
N8 S4 C47 107.61(14) . . ?
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 C6 1.368(5) . ?
C1 C2 1.397(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.400(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(4) . ?
C7 N1 1.485(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 S1 1.760(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.304(4) . ?
C9 C19 1.419(4) . ?
C9 N1 1.446(3) . ?
C10 N2 1.384(3) . ?
C10 C11 1.412(4) . ?
C10 C15 1.422(4) . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.409(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.417(4) . ?
C16 N3 1.368(3) . ?
C16 C19 1.399(4) . ?
C17 C18 1.363(4) . ?
C17 N3 1.379(4) . ?
C17 N4 1.418(3) . ?
C18 C19 1.424(4) . ?
C18 H18 0.9300 . ?
C20 S2 1.760(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N4 1.486(4) . ?
C21 C22 1.498(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.389(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.387(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.400(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.393(4) . ?
C28 C33 1.393(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.400(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.387(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.509(4) . ?
C34 N5 1.482(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 S3 1.763(3) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 N6 1.307(3) . ?
C36 C46 1.412(4) . ?
C36 N5 1.445(3) . ?
C37 N6 1.382(3) . ?
C37 C38 1.412(4) . ?
C37 C42 1.422(4) . ?
C38 C39 1.373(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.406(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.373(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.414(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.425(3) . ?
C43 N7 1.357(3) . ?
C43 C46 1.398(3) . ?
C44 C45 1.367(4) . ?
C44 N7 1.381(3) . ?
C44 N8 1.421(3) . ?
C45 C46 1.426(4) . ?
C45 H45 0.9300 . ?
C47 S4 1.759(3) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.479(5) . ?
C48 N8 1.494(4) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 C54 1.358(7) . ?
C49 C50 1.397(10) . ?
C50 C51 1.471(11) . ?
C50 H50 0.9300 . ?
C51 C52 1.390(16) . ?
C51 H51 0.9300 . ?
C52 C53 1.240(15) . ?
C52 H52 0.9300 . ?
C53 C54 1.650(11) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
N1 S1 1.648(2) . ?
N3 H1B 0.92(4) . ?
N4 S2 1.654(2) . ?
N5 S3 1.633(2) . ?
N7 H1A 0.84(4) . ?
N8 S4 1.651(3) . ?
O1 S1 1.427(2) . ?
O2 S1 1.439(2) . ?
O3 S2 1.424(2) . ?
O4 S2 1.436(2) . ?
O5 S3 1.435(2) . ?
O6 S3 1.434(2) . ?
O7 S4 1.438(2) . ?
O8 S4 1.432(2) . ?
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
C6 C1 C2 C3 -3.0(6) . . . . ?
C1 C2 C3 C4 -1.9(8) . . . . ?
C2 C3 C4 C5 4.4(11) . . . . ?
C3 C4 C5 C6 -2.2(11) . . . . ?
C2 C1 C6 C5 5.2(6) . . . . ?
C2 C1 C6 C7 -174.0(3) . . . . ?
C4 C5 C6 C1 -2.7(8) . . . . ?
C4 C5 C6 C7 176.6(5) . . . . ?
C1 C6 C7 N1 -44.8(4) . . . . ?
C5 C6 C7 N1 136.0(4) . . . . ?
N2 C10 C11 C12 -179.3(3) . . . . ?
C15 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
N2 C10 C15 C14 -179.6(3) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
N2 C10 C15 C16 0.5(4) . . . . ?
C11 C10 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 N3 0.6(5) . . . . ?
C10 C15 C16 N3 -179.5(3) . . . . ?
C14 C15 C16 C19 -179.9(3) . . . . ?
C10 C15 C16 C19 0.1(4) . . . . ?
N3 C17 C18 C19 0.8(3) . . . . ?
N4 C17 C18 C19 176.6(3) . . . . ?
N3 C16 C19 C9 178.6(2) . . . . ?
C15 C16 C19 C9 -1.0(4) . . . . ?
N3 C16 C19 C18 -1.0(3) . . . . ?
C15 C16 C19 C18 179.3(2) . . . . ?
N2 C9 C19 C16 1.5(4) . . . . ?
N1 C9 C19 C16 -175.9(2) . . . . ?
N2 C9 C19 C18 -178.9(3) . . . . ?
N1 C9 C19 C18 3.7(5) . . . . ?
C17 C18 C19 C16 0.1(3) . . . . ?
C17 C18 C19 C9 -179.5(3) . . . . ?
N4 C21 C22 C27 113.8(3) . . . . ?
N4 C21 C22 C23 -66.9(3) . . . . ?
C27 C22 C23 C24 0.4(5) . . . . ?
C21 C22 C23 C24 -178.9(3) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C26 -0.1(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C23 C22 C27 C26 -0.1(5) . . . . ?
C21 C22 C27 C26 179.2(3) . . . . ?
C25 C26 C27 C22 -0.3(6) . . . . ?
C33 C28 C29 C30 0.7(6) . . . . ?
C28 C29 C30 C31 -0.6(6) . . . . ?
C29 C30 C31 C32 -0.3(6) . . . . ?
C30 C31 C32 C33 1.0(6) . . . . ?
C31 C32 C33 C28 -0.9(5) . . . . ?
C31 C32 C33 C34 176.0(3) . . . . ?
C29 C28 C33 C32 0.1(5) . . . . ?
C29 C28 C33 C34 -176.9(3) . . . . ?
C32 C33 C34 N5 135.4(3) . . . . ?
C28 C33 C34 N5 -47.7(4) . . . . ?
N6 C37 C38 C39 177.4(2) . . . . ?
C42 C37 C38 C39 -2.9(4) . . . . ?
C37 C38 C39 C40 1.5(4) . . . . ?
C38 C39 C40 C41 0.7(4) . . . . ?
C39 C40 C41 C42 -1.4(4) . . . . ?
C40 C41 C42 C37 -0.1(4) . . . . ?
C40 C41 C42 C43 178.7(3) . . . . ?
N6 C37 C42 C41 -178.2(2) . . . . ?
C38 C37 C42 C41 2.2(4) . . . . ?
N6 C37 C42 C43 2.9(4) . . . . ?
C38 C37 C42 C43 -176.7(2) . . . . ?
C41 C42 C43 N7 -1.0(5) . . . . ?
C37 C42 C43 N7 177.8(3) . . . . ?
C41 C42 C43 C46 -179.3(3) . . . . ?
C37 C42 C43 C46 -0.4(4) . . . . ?
N7 C44 C45 C46 0.4(3) . . . . ?
N8 C44 C45 C46 178.2(3) . . . . ?
N7 C43 C46 C36 179.0(2) . . . . ?
C42 C43 C46 C36 -2.4(4) . . . . ?
N7 C43 C46 C45 -1.5(3) . . . . ?
C42 C43 C46 C45 177.1(2) . . . . ?
N6 C36 C46 C43 3.3(4) . . . . ?
N5 C36 C46 C43 -174.6(2) . . . . ?
N6 C36 C46 C45 -176.1(3) . . . . ?
N5 C36 C46 C45 6.0(5) . . . . ?
C44 C45 C46 C43 0.6(3) . . . . ?
C44 C45 C46 C36 -179.9(3) . . . . ?
N8 C48 C49 C54 94.2(4) . . . . ?
N8 C48 C49 C50 -86.7(7) . . . . ?
C54 C49 C50 C51 12.9(16) . . . . ?
C48 C49 C50 C51 -166.2(10) . . . . ?
C49 C50 C51 C52 -35.1(16) . . . . ?
C50 C51 C52 C53 46(3) . . . . ?
C51 C52 C53 C54 -30(3) . . . . ?
C50 C49 C54 C53 9.5(9) . . . . ?
C48 C49 C54 C53 -171.4(5) . . . . ?
C52 C53 C54 C49 -4.3(16) . . . . ?
N2 C9 N1 C7 -36.7(3) . . . . ?
C19 C9 N1 C7 140.9(2) . . . . ?
N2 C9 N1 S1 103.0(2) . . . . ?
C19 C9 N1 S1 -79.5(3) . . . . ?
C6 C7 N1 C9 -79.3(3) . . . . ?
C6 C7 N1 S1 139.9(2) . . . . ?
C19 C9 N2 C10 -1.0(4) . . . . ?
N1 C9 N2 C10 176.5(2) . . . . ?
C11 C10 N2 C9 -179.8(3) . . . . ?
C15 C10 N2 C9 -0.1(4) . . . . ?
C19 C16 N3 C17 1.5(3) . . . . ?
C15 C16 N3 C17 -178.9(3) . . . . ?
C18 C17 N3 C16 -1.5(3) . . . . ?
N4 C17 N3 C16 -177.7(2) . . . . ?
C18 C17 N4 C21 -29.3(4) . . . . ?
N3 C17 N4 C21 146.1(3) . . . . ?
C18 C17 N4 S2 117.9(3) . . . . ?
N3 C17 N4 S2 -66.6(3) . . . . ?
C22 C21 N4 C17 -68.2(3) . . . . ?
C22 C21 N4 S2 144.3(2) . . . . ?
N6 C36 N5 C34 -50.1(3) . . . . ?
C46 C36 N5 C34 127.9(3) . . . . ?
N6 C36 N5 S3 94.0(3) . . . . ?
C46 C36 N5 S3 -87.9(3) . . . . ?
C33 C34 N5 C36 -88.8(3) . . . . ?
C33 C34 N5 S3 127.3(2) . . . . ?
C46 C36 N6 C37 -1.0(4) . . . . ?
N5 C36 N6 C37 177.0(2) . . . . ?
C38 C37 N6 C36 177.4(2) . . . . ?
C42 C37 N6 C36 -2.3(4) . . . . ?
C46 C43 N7 C44 1.8(3) . . . . ?
C42 C43 N7 C44 -176.7(3) . . . . ?
C45 C44 N7 C43 -1.4(3) . . . . ?
N8 C44 N7 C43 -179.4(3) . . . . ?
C45 C44 N8 C48 -55.5(4) . . . . ?
N7 C44 N8 C48 122.0(3) . . . . ?
C45 C44 N8 S4 92.1(4) . . . . ?
N7 C44 N8 S4 -90.4(3) . . . . ?
C49 C48 N8 C44 -58.7(4) . . . . ?
C49 C48 N8 S4 155.3(3) . . . . ?
C9 N1 S1 O1 169.74(19) . . . . ?
C7 N1 S1 O1 -50.1(2) . . . . ?
C9 N1 S1 O2 41.9(2) . . . . ?
C7 N1 S1 O2 -177.94(18) . . . . ?
C9 N1 S1 C8 -72.7(2) . . . . ?
C7 N1 S1 C8 67.5(2) . . . . ?
C17 N4 S2 O3 40.3(2) . . . . ?
C21 N4 S2 O3 -172.9(2) . . . . ?
C17 N4 S2 O4 169.2(2) . . . . ?
C21 N4 S2 O4 -44.1(2) . . . . ?
C17 N4 S2 C20 -75.3(2) . . . . ?
C21 N4 S2 C20 71.4(2) . . . . ?
C36 N5 S3 O6 172.60(19) . . . . ?
C34 N5 S3 O6 -43.9(2) . . . . ?
C36 N5 S3 O5 43.8(2) . . . . ?
C34 N5 S3 O5 -172.64(19) . . . . ?
C36 N5 S3 C35 -71.9(2) . . . . ?
C34 N5 S3 C35 71.6(2) . . . . ?
C44 N8 S4 O8 47.8(2) . . . . ?
C48 N8 S4 O8 -165.9(2) . . . . ?
C44 N8 S4 O7 175.60(19) . . . . ?
C48 N8 S4 O7 -38.1(2) . . . . ?
C44 N8 S4 C47 -68.0(2) . . . . ?
C48 N8 S4 C47 78.3(2) . . . . ?
