#------------------------------------------------------------------------------
#$Date: 2020-04-08 02:28:59 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038211.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_4038211
loop_
_publ_author_name
'Helberg, Julian'
'Ampßler, Torsten'
'Zipse, Hendrik'
_publ_section_title
;
 Pyridinyl Amide Ion Pairs as Lewis Base Organocatalysts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00114
_journal_year                    2020
_chemical_formula_moiety         'C12 H11 N2 O2 S, C11 H15 N2'
_chemical_formula_sum            'C23 H26 N4 O2 S'
_chemical_formula_weight         422.54
_chemical_name_common            586a
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_code                C12H11N2O2S_C11H15N2_xv096_zipse
_audit_creation_method           'APEX3 v2017.3-0'
_audit_update_record             06-Feb-19
_cell_angle_alpha                90
_cell_angle_beta                 91.9590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5001(3)
_cell_length_b                   14.8911(4)
_cell_length_c                   30.2630(9)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    106.(2)
_cell_measurement_theta_max      25.3319
_cell_measurement_theta_min      2.5717
_cell_volume                     4278.7(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      106.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            63746
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'rotating anode (TXS)'
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0385
_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)+(0.0379P)²+2.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6407
_reflns_number_total             7815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00114_si_002.cif
_cod_data_source_block           xv096
_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/ACS/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               4038211
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.995
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
S1 S 0.47535(5) 0.28484(3) 0.42117(2) 0.01976(11) Uani 1 1 d . . . . .
S2 S 0.41340(5) 0.76935(3) 0.32010(2) 0.02305(12) Uani 1 1 d . . . . .
O1 O 0.40701(13) 0.37191(8) 0.41726(4) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.44655(15) 0.22424(9) 0.38444(4) 0.0287(3) Uani 1 1 d . . . . .
O3 O 0.39341(15) 0.84296(10) 0.28915(4) 0.0350(4) Uani 1 1 d . . . . .
O4 O 0.34377(14) 0.68603(10) 0.30725(4) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.63932(16) 0.28749(10) 0.42895(5) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.84404(16) 0.33601(10) 0.46288(5) 0.0238(4) Uani 1 1 d . . . . .
N3 N 0.79414(15) 0.16840(10) 0.32106(5) 0.0205(3) Uani 1 1 d . . . . .
N4 N 0.97796(16) 0.19071(10) 0.36500(5) 0.0208(3) Uani 1 1 d . . . . .
N5 N 0.57602(16) 0.76083(11) 0.32993(5) 0.0231(3) Uani 1 1 d . . . . .
N6 N 0.77392(16) 0.69137(10) 0.35823(5) 0.0222(3) Uani 1 1 d . . . . .
N7 N 0.26701(15) 0.37091(10) 0.27742(5) 0.0200(3) Uani 1 1 d . . . . .
N8 N 0.08658(16) 0.35385(10) 0.23152(5) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.70181(18) 0.34021(12) 0.46190(6) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.63182(18) 0.39387(12) 0.49276(6) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.531857 0.396607 0.492007 0.024 Uiso 1 1 calc R U . . .
C3 C 0.70871(19) 0.44211(12) 0.52388(6) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.662229 0.478384 0.544694 0.027 Uiso 1 1 calc R U . . .
C4 C 0.85468(19) 0.43748(13) 0.52470(6) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.910420 0.470096 0.545842 0.031 Uiso 1 1 calc R U . . .
C5 C 0.91540(19) 0.38376(13) 0.49366(7) 0.0264(4) Uani 1 1 d . . . . .
H5 H 1.015290 0.380321 0.494111 0.032 Uiso 1 1 calc R U . . .
C6 C 0.40208(18) 0.23203(12) 0.46792(6) 0.0173(4) Uani 1 1 d . . . . .
C7 C 0.44685(19) 0.14632(12) 0.47965(6) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.517018 0.117107 0.463254 0.026 Uiso 1 1 calc R U . . .
C8 C 0.38885(19) 0.10354(13) 0.51535(6) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.419295 0.044609 0.522983 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2873(2) 0.14481(12) 0.54024(6) 0.0227(4) Uani 1 1 d . . . . .
C10 C 0.2440(2) 0.23072(13) 0.52817(6) 0.0246(4) Uani 1 1 d . . . . .
H10 H 0.174210 0.260011 0.544689 0.029 Uiso 1 1 calc R U . . .
C11 C 0.30063(19) 0.27459(12) 0.49248(6) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.270216 0.333519 0.484849 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2274(2) 0.09928(14) 0.58005(6) 0.0321(5) Uani 1 1 d . . . . .
H12A H 0.125611 0.109690 0.580288 0.048 Uiso 1 1 calc R U . . .
H12B H 0.272060 0.123992 0.607075 0.048 Uiso 1 1 calc R U . . .
H12C H 0.245829 0.034604 0.578614 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8380(2) 0.19168(12) 0.36180(6) 0.0228(4) Uani 1 1 d . . . . .
H13 H 0.778029 0.206761 0.385156 0.027 Uiso 1 1 calc R U . . .
C14 C 0.91243(19) 0.15169(12) 0.29614(6) 0.0200(4) Uani 1 1 d . . . . .
C15 C 1.02942(19) 0.16645(11) 0.32417(6) 0.0195(4) Uani 1 1 d . . . . .
C16 C 1.16675(19) 0.15821(12) 0.30991(6) 0.0236(4) Uani 1 1 d . . . . .
H16 H 1.246362 0.168573 0.329084 0.028 Uiso 1 1 calc R U . . .
C17 C 1.1800(2) 0.13405(13) 0.26622(6) 0.0265(4) Uani 1 1 d . . . . .
H17 H 1.271548 0.127929 0.254892 0.032 Uiso 1 1 calc R U . . .
C18 C 1.0621(2) 0.11826(13) 0.23801(6) 0.0270(4) Uani 1 1 d . . . . .
H18 H 1.076385 0.101185 0.208250 0.032 Uiso 1 1 calc R U . . .
C19 C 0.9259(2) 0.12679(12) 0.25219(6) 0.0235(4) Uani 1 1 d . . . . .
H19 H 0.846250 0.116261 0.233044 0.028 Uiso 1 1 calc R U . . .
C20 C 0.64571(19) 0.15698(14) 0.30638(6) 0.0282(4) Uani 1 1 d . . . . .
H20A H 0.637223 0.163993 0.273865 0.034 Uiso 1 1 calc R U . . .
H20B H 0.587864 0.204214 0.319925 0.034 Uiso 1 1 calc R U . . .
C21 C 0.5911(2) 0.06607(16) 0.31910(9) 0.0452(6) Uani 1 1 d . . . . .
H21A H 0.493837 0.059205 0.307743 0.068 Uiso 1 1 calc R U . . .
H21B H 0.593816 0.060521 0.351385 0.068 Uiso 1 1 calc R U . . .
H21C H 0.650031 0.019264 0.306455 0.068 Uiso 1 1 calc R U . . .
C22 C 1.0631(2) 0.20173(13) 0.40627(6) 0.0240(4) Uani 1 1 d . . . . .
H22A H 1.007244 0.233338 0.428514 0.029 Uiso 1 1 calc R U . . .
H22B H 1.147520 0.238328 0.400576 0.029 Uiso 1 1 calc R U . . .
C23 C 1.1074(2) 0.11035(13) 0.42379(6) 0.0270(4) Uani 1 1 d . . . . .
H23A H 1.159496 0.117562 0.452074 0.040 Uiso 1 1 calc R U . . .
H23B H 1.167754 0.080952 0.402512 0.040 Uiso 1 1 calc R U . . .
H23C H 1.023585 0.073424 0.428109 0.040 Uiso 1 1 calc R U . . .
C24 C 0.63204(18) 0.69349(12) 0.35699(6) 0.0190(4) Uani 1 1 d . . . . .
C25 C 0.55505(19) 0.63185(12) 0.38203(6) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.455015 0.633188 0.380801 0.026 Uiso 1 1 calc R U . . .
C26 C 0.6254(2) 0.56973(12) 0.40825(6) 0.0241(4) Uani 1 1 d . . . . .
H26 H 0.574129 0.528256 0.425323 0.029 Uiso 1 1 calc R U . . .
C27 C 0.77112(19) 0.56803(12) 0.40960(6) 0.0236(4) Uani 1 1 d . . . . .
H27 H 0.822252 0.526126 0.427549 0.028 Uiso 1 1 calc R U . . .
C28 C 0.83901(19) 0.62959(13) 0.38385(6) 0.0237(4) Uani 1 1 d . . . . .
H28 H 0.939025 0.628156 0.384287 0.028 Uiso 1 1 calc R U . . .
C29 C 0.33256(18) 0.80417(12) 0.36938(6) 0.0200(4) Uani 1 1 d . . . . .
C30 C 0.37187(19) 0.88570(13) 0.38833(6) 0.0234(4) Uani 1 1 d . . . . .
H30 H 0.440461 0.922191 0.374921 0.028 Uiso 1 1 calc R U . . .
C31 C 0.31074(19) 0.91349(13) 0.42676(6) 0.0240(4) Uani 1 1 d . . . . .
H31 H 0.338021 0.969382 0.439540 0.029 Uiso 1 1 calc R U . . .
C32 C 0.21008(19) 0.86149(13) 0.44720(6) 0.0233(4) Uani 1 1 d . . . . .
C33 C 0.1713(2) 0.78050(13) 0.42745(6) 0.0256(4) Uani 1 1 d . . . . .
H33 H 0.101761 0.744286 0.440566 0.031 Uiso 1 1 calc R U . . .
C34 C 0.23219(19) 0.75158(12) 0.38895(6) 0.0226(4) Uani 1 1 d . . . . .
H34 H 0.205015 0.695773 0.376061 0.027 Uiso 1 1 calc R U . . .
C35 C 0.1465(2) 0.89025(15) 0.49000(7) 0.0334(5) Uani 1 1 d . . . . .
H35A H 0.045431 0.876940 0.488881 0.050 Uiso 1 1 calc R U . . .
H35B H 0.160687 0.954914 0.494214 0.050 Uiso 1 1 calc R U . . .
H35C H 0.192162 0.857575 0.514672 0.050 Uiso 1 1 calc R U . . .
C36 C 0.2263(2) 0.35069(12) 0.23605(6) 0.0214(4) Uani 1 1 d . . . . .
H36 H 0.288094 0.336115 0.213098 0.026 Uiso 1 1 calc R U . . .
C37 C 0.14709(19) 0.38728(12) 0.30139(6) 0.0198(4) Uani 1 1 d . . . . .
C38 C 0.03224(19) 0.37643(12) 0.27210(6) 0.0200(4) Uani 1 1 d . . . . .
C39 C -0.1062(2) 0.38402(12) 0.28571(6) 0.0240(4) Uani 1 1 d . . . . .
H39 H -0.184825 0.377125 0.265736 0.029 Uiso 1 1 calc R U . . .
C40 C -0.1217(2) 0.40222(13) 0.33008(6) 0.0269(4) Uani 1 1 d . . . . .
H40 H -0.213940 0.407639 0.340978 0.032 Uiso 1 1 calc R U . . .
C41 C -0.0059(2) 0.41291(13) 0.35945(6) 0.0275(4) Uani 1 1 d . . . . .
H41 H -0.022145 0.425511 0.389623 0.033 Uiso 1 1 calc R U . . .
C42 C 0.1308(2) 0.40581(12) 0.34615(6) 0.0236(4) Uani 1 1 d . . . . .
H42 H 0.209170 0.413072 0.366176 0.028 Uiso 1 1 calc R U . . .
C43 C 0.41326(19) 0.37399(13) 0.29519(6) 0.0265(4) Uani 1 1 d . . . . .
H43A H 0.474990 0.341470 0.274895 0.032 Uiso 1 1 calc R U . . .
H43B H 0.418782 0.343122 0.324165 0.032 Uiso 1 1 calc R U . . .
C44 C 0.4649(2) 0.46820(17) 0.30071(9) 0.0516(7) Uani 1 1 d . . . . .
H44A H 0.558052 0.467749 0.315673 0.077 Uiso 1 1 calc R U . . .
H44B H 0.399050 0.502208 0.318488 0.077 Uiso 1 1 calc R U . . .
H44C H 0.471548 0.496441 0.271611 0.077 Uiso 1 1 calc R U . . .
C45 C 0.0053(2) 0.33999(12) 0.18977(6) 0.0223(4) Uani 1 1 d . . . . .
H45A H -0.082575 0.307083 0.195713 0.027 Uiso 1 1 calc R U . . .
H45B H 0.061025 0.303157 0.169480 0.027 Uiso 1 1 calc R U . . .
C46 C -0.0304(2) 0.42906(12) 0.16814(6) 0.0254(4) Uani 1 1 d . . . . .
H46A H -0.081789 0.418498 0.139987 0.038 Uiso 1 1 calc R U . . .
H46B H 0.056584 0.462041 0.162748 0.038 Uiso 1 1 calc R U . . .
H46C H -0.089243 0.464343 0.187678 0.038 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
O2 S1 O1 114.87(8) . . ?
O2 S1 N1 106.92(8) . . ?
O1 S1 N1 115.38(8) . . ?
O2 S1 C6 105.40(8) . . ?
O1 S1 C6 105.85(8) . . ?
N1 S1 C6 107.77(8) . . ?
O3 S2 O4 115.11(9) . . ?
O3 S2 N5 106.86(8) . . ?
O4 S2 N5 114.72(8) . . ?
O3 S2 C29 105.69(8) . . ?
O4 S2 C29 105.54(8) . . ?
N5 S2 C29 108.38(8) . . ?
C1 N1 S1 121.39(12) . . ?
C5 N2 C1 118.24(16) . . ?
C13 N3 C14 108.27(15) . . ?
C13 N3 C20 125.06(15) . . ?
C14 N3 C20 126.56(15) . . ?
C13 N4 C15 108.59(15) . . ?
C13 N4 C22 125.36(15) . . ?
C15 N4 C22 125.60(15) . . ?
C24 N5 S2 121.68(13) . . ?
C28 N6 C24 118.25(16) . . ?
C36 N7 C37 108.21(15) . . ?
C36 N7 C43 126.16(15) . . ?
C37 N7 C43 125.62(15) . . ?
C36 N8 C38 108.47(15) . . ?
C36 N8 C45 125.13(15) . . ?
C38 N8 C45 126.34(15) . . ?
N2 C1 N1 113.12(16) . . ?
N2 C1 C2 120.28(17) . . ?
N1 C1 C2 126.59(16) . . ?
C3 C2 C1 119.83(17) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.57(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 117.31(18) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N2 C5 C4 124.77(17) . . ?
N2 C5 H5 117.6 . . ?
C4 C5 H5 117.6 . . ?
C7 C6 C11 119.65(16) . . ?
C7 C6 S1 118.98(14) . . ?
C11 C6 S1 121.37(14) . . ?
C8 C7 C6 119.74(17) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.49(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 118.04(17) . . ?
C8 C9 C12 121.45(18) . . ?
C10 C9 C12 120.49(18) . . ?
C11 C10 C9 121.32(17) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 119.76(17) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 N3 110.17(16) . . ?
N4 C13 H13 124.9 . . ?
N3 C13 H13 124.9 . . ?
C19 C14 C15 121.82(17) . . ?
C19 C14 N3 131.74(17) . . ?
C15 C14 N3 106.43(15) . . ?
N4 C15 C14 106.54(15) . . ?
N4 C15 C16 131.20(17) . . ?
C14 C15 C16 122.25(17) . . ?
C17 C16 C15 115.89(17) . . ?
C17 C16 H16 122.1 . . ?
C15 C16 H16 122.1 . . ?
C16 C17 C18 121.93(18) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 122.09(18) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C14 116.02(18) . . ?
C18 C19 H19 122.0 . . ?
C14 C19 H19 122.0 . . ?
N3 C20 C21 111.19(16) . . ?
N3 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N3 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C23 109.54(15) . . ?
N4 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
N4 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 C24 N5 113.33(15) . . ?
N6 C24 C25 120.42(16) . . ?
N5 C24 C25 126.25(16) . . ?
C26 C25 C24 119.78(17) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 119.64(18) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 117.29(17) . . ?
C28 C27 H27 121.4 . . ?
C26 C27 H27 121.4 . . ?
N6 C28 C27 124.62(17) . . ?
N6 C28 H28 117.7 . . ?
C27 C28 H28 117.7 . . ?
C34 C29 C30 119.87(17) . . ?
C34 C29 S2 121.20(14) . . ?
C30 C29 S2 118.93(14) . . ?
C31 C30 C29 119.66(17) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 121.50(18) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C33 C32 C31 117.89(17) . . ?
C33 C32 C35 120.47(18) . . ?
C31 C32 C35 121.63(18) . . ?
C34 C33 C32 121.23(18) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C29 C34 C33 119.84(18) . . ?
C29 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N8 C36 N7 110.23(16) . . ?
N8 C36 H36 124.9 . . ?
N7 C36 H36 124.9 . . ?
C38 C37 N7 106.58(15) . . ?
C38 C37 C42 122.05(17) . . ?
N7 C37 C42 131.27(17) . . ?
N8 C38 C37 106.51(15) . . ?
N8 C38 C39 131.49(17) . . ?
C37 C38 C39 121.92(17) . . ?
C40 C39 C38 115.79(17) . . ?
C40 C39 H39 122.1 . . ?
C38 C39 H39 122.1 . . ?
C39 C40 C41 122.10(18) . . ?
C39 C40 H40 119.0 . . ?
C41 C40 H40 119.0 . . ?
C42 C41 C40 122.31(18) . . ?
C42 C41 H41 118.8 . . ?
C40 C41 H41 118.8 . . ?
C41 C42 C37 115.84(17) . . ?
C41 C42 H42 122.1 . . ?
C37 C42 H42 122.1 . . ?
N7 C43 C44 111.85(16) . . ?
N7 C43 H43A 109.2 . . ?
C44 C43 H43A 109.2 . . ?
N7 C43 H43B 109.2 . . ?
C44 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C45 C46 110.60(15) . . ?
N8 C45 H45A 109.5 . . ?
C46 C45 H45A 109.5 . . ?
N8 C45 H45B 109.5 . . ?
C46 C45 H45B 109.5 . . ?
H45A C45 H45B 108.1 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
S1 O2 1.4507(13) . ?
S1 O1 1.4532(13) . ?
S1 N1 1.5679(16) . ?
S1 C6 1.7810(18) . ?
S2 O3 1.4500(14) . ?
S2 O4 1.4528(15) . ?
S2 N5 1.5685(16) . ?
S2 C29 1.7781(18) . ?
N1 C1 1.387(2) . ?
N2 C5 1.338(3) . ?
N2 C1 1.352(2) . ?
N3 C13 1.334(2) . ?
N3 C14 1.397(2) . ?
N3 C20 1.474(2) . ?
N4 C13 1.329(2) . ?
N4 C15 1.392(2) . ?
N4 C22 1.474(2) . ?
N5 C24 1.389(2) . ?
N6 C28 1.341(2) . ?
N6 C24 1.348(2) . ?
N7 C36 1.332(2) . ?
N7 C37 1.393(2) . ?
N7 C43 1.473(2) . ?
N8 C36 1.330(2) . ?
N8 C38 1.390(2) . ?
N8 C45 1.472(2) . ?
C1 C2 1.413(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 C11 1.390(2) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C12 1.510(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 C19 1.391(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.505(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.515(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.411(3) . ?
C25 C26 1.377(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.383(3) . ?
C29 C30 1.388(3) . ?
C30 C31 1.381(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.390(3) . ?
C32 C35 1.510(3) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36 0.9500 . ?
C37 C38 1.392(3) . ?
C37 C42 1.396(3) . ?
C38 C39 1.396(3) . ?
C39 C40 1.383(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.400(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.377(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.494(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.513(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
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
O2 S1 N1 C1 179.60(13) . . . . ?
O1 S1 N1 C1 50.48(16) . . . . ?
C6 S1 N1 C1 -67.51(15) . . . . ?
O3 S2 N5 C24 -176.94(14) . . . . ?
O4 S2 N5 C24 -48.06(17) . . . . ?
C29 S2 N5 C24 69.57(16) . . . . ?
C5 N2 C1 N1 -179.46(15) . . . . ?
C5 N2 C1 C2 0.0(2) . . . . ?
S1 N1 C1 N2 -178.20(12) . . . . ?
S1 N1 C1 C2 2.4(2) . . . . ?
N2 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C2 C3 179.47(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C1 N2 C5 C4 -0.1(3) . . . . ?
C3 C4 C5 N2 0.1(3) . . . . ?
O2 S1 C6 C7 57.22(16) . . . . ?
O1 S1 C6 C7 179.33(14) . . . . ?
N1 S1 C6 C7 -56.69(16) . . . . ?
O2 S1 C6 C11 -122.24(15) . . . . ?
O1 S1 C6 C11 -0.13(17) . . . . ?
N1 S1 C6 C11 123.85(15) . . . . ?
C11 C6 C7 C8 0.8(3) . . . . ?
S1 C6 C7 C8 -178.66(14) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C12 -178.02(17) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C12 C9 C10 C11 178.15(17) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
S1 C6 C11 C10 178.77(14) . . . . ?
C15 N4 C13 N3 0.6(2) . . . . ?
C22 N4 C13 N3 -171.98(16) . . . . ?
C14 N3 C13 N4 -0.3(2) . . . . ?
C20 N3 C13 N4 176.10(16) . . . . ?
C13 N3 C14 C19 -179.02(19) . . . . ?
C20 N3 C14 C19 4.6(3) . . . . ?
C13 N3 C14 C15 -0.14(19) . . . . ?
C20 N3 C14 C15 -176.48(16) . . . . ?
C13 N4 C15 C14 -0.7(2) . . . . ?
C22 N4 C15 C14 171.89(16) . . . . ?
C13 N4 C15 C16 177.96(18) . . . . ?
C22 N4 C15 C16 -9.4(3) . . . . ?
C19 C14 C15 N4 179.52(16) . . . . ?
N3 C14 C15 N4 0.50(19) . . . . ?
C19 C14 C15 C16 0.7(3) . . . . ?
N3 C14 C15 C16 -178.30(16) . . . . ?
N4 C15 C16 C17 -178.76(18) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 -0.5(3) . . . . ?
N3 C14 C19 C18 178.28(18) . . . . ?
C13 N3 C20 C21 -81.7(2) . . . . ?
C14 N3 C20 C21 94.1(2) . . . . ?
C13 N4 C22 C23 98.0(2) . . . . ?
C15 N4 C22 C23 -73.4(2) . . . . ?
C28 N6 C24 N5 179.13(16) . . . . ?
C28 N6 C24 C25 -0.2(3) . . . . ?
S2 N5 C24 N6 173.96(13) . . . . ?
S2 N5 C24 C25 -6.8(3) . . . . ?
N6 C24 C25 C26 0.7(3) . . . . ?
N5 C24 C25 C26 -178.55(17) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?
C24 N6 C28 C27 -0.7(3) . . . . ?
C26 C27 C28 N6 0.9(3) . . . . ?
O3 S2 C29 C34 126.32(16) . . . . ?
O4 S2 C29 C34 3.93(17) . . . . ?
N5 S2 C29 C34 -119.42(15) . . . . ?
O3 S2 C29 C30 -53.80(16) . . . . ?
O4 S2 C29 C30 -176.18(14) . . . . ?
N5 S2 C29 C30 60.47(16) . . . . ?
C34 C29 C30 C31 0.3(3) . . . . ?
S2 C29 C30 C31 -179.60(14) . . . . ?
C29 C30 C31 C32 0.1(3) . . . . ?
C30 C31 C32 C33 -0.7(3) . . . . ?
C30 C31 C32 C35 177.99(17) . . . . ?
C31 C32 C33 C34 0.9(3) . . . . ?
C35 C32 C33 C34 -177.75(18) . . . . ?
C30 C29 C34 C33 0.0(3) . . . . ?
S2 C29 C34 C33 179.85(14) . . . . ?
C32 C33 C34 C29 -0.6(3) . . . . ?
C38 N8 C36 N7 -0.6(2) . . . . ?
C45 N8 C36 N7 176.61(15) . . . . ?
C37 N7 C36 N8 0.7(2) . . . . ?
C43 N7 C36 N8 179.66(16) . . . . ?
C36 N7 C37 C38 -0.43(19) . . . . ?
C43 N7 C37 C38 -179.43(16) . . . . ?
C36 N7 C37 C42 175.83(19) . . . . ?
C43 N7 C37 C42 -3.2(3) . . . . ?
C36 N8 C38 C37 0.35(19) . . . . ?
C45 N8 C38 C37 -176.85(16) . . . . ?
C36 N8 C38 C39 -176.31(19) . . . . ?
C45 N8 C38 C39 6.5(3) . . . . ?
N7 C37 C38 N8 0.05(19) . . . . ?
C42 C37 C38 N8 -176.63(16) . . . . ?
N7 C37 C38 C39 177.10(16) . . . . ?
C42 C37 C38 C39 0.4(3) . . . . ?
N8 C38 C39 C40 175.71(18) . . . . ?
C37 C38 C39 C40 -0.5(3) . . . . ?
C38 C39 C40 C41 0.4(3) . . . . ?
C39 C40 C41 C42 -0.2(3) . . . . ?
C40 C41 C42 C37 0.0(3) . . . . ?
C38 C37 C42 C41 -0.2(3) . . . . ?
N7 C37 C42 C41 -175.93(18) . . . . ?
C36 N7 C43 C44 104.0(2) . . . . ?
C37 N7 C43 C44 -77.1(2) . . . . ?
C36 N8 C45 C46 -96.1(2) . . . . ?
C38 N8 C45 C46 80.6(2) . . . . ?
