#------------------------------------------------------------------------------
#$Date: 2025-01-06 12:22:46 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/39/7133980.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_7133980
loop_
_publ_author_name
'Ge, Shen'
'Zhu, Yi-Ming'
'Xu, Xiao-Ping'
'Zi, You'
'Ji, Shun-Jun'
_publ_section_title
;
 Palladium-catalyzed cascade cyclization of isocyanides with
 di-(o-iodophenyl)sulfonylguanidines: access to heterocyclic fused
 quinazolines.
;
_journal_issue                   98
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14613
_journal_page_last               14616
_journal_paper_doi               10.1039/d4cc04084h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C28 H20 F2 N4 O3 S'
_chemical_formula_sum            'C28 H20 F2 N4 O3 S'
_chemical_formula_weight         530.54
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-07-27 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                97.667(2)
_cell_angle_beta                 98.389(2)
_cell_angle_gamma                98.438(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8435(7)
_cell_length_b                   12.5404(8)
_cell_length_c                   18.9000(13)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.21
_cell_volume                     2483.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0826
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            120964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.206
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         11366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0503
_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)+(0.0469P)²+0.9762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6782
_reflns_number_total             11366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc04084h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7133979--7133980.cif.'
_cod_database_code               7133980
_shelx_shelxl_version_number     2016/6
_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   0.913
_shelx_estimated_absorpt_t_max   0.964
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
S1 S 0.51432(5) 0.78717(4) 0.22601(3) 0.04090(15) Uani 1 1 d . . . . .
O1 O 0.29265(16) -0.10260(12) -0.03889(9) 0.0587(4) Uani 1 1 d . . . . .
O2 O 0.62799(15) 0.86496(12) 0.23192(8) 0.0537(4) Uani 1 1 d . . . . .
O3 O 0.39944(15) 0.82118(12) 0.19654(9) 0.0560(4) Uani 1 1 d . . . . .
N1 N 0.46579(16) 0.33945(13) 0.05428(9) 0.0398(4) Uani 1 1 d . . . . .
N2 N 0.48636(15) 0.50273(13) 0.11870(8) 0.0354(4) Uani 1 1 d . . . . .
N3 N 0.33936(17) 0.57408(14) 0.18362(9) 0.0422(4) Uani 1 1 d . . . . .
N4 N 0.54097(16) 0.67697(13) 0.18261(9) 0.0402(4) Uani 1 1 d . . . . .
F1 F 0.87928(13) 0.40616(12) -0.01278(9) 0.0729(4) Uani 1 1 d . . . . .
F2 F -0.01329(15) 0.20652(15) 0.07780(10) 0.0990(6) Uani 1 1 d . . . . .
C1 C 0.2661(3) -0.1450(2) -0.11428(13) 0.0672(8) Uani 1 1 d . . . . .
H1A H 0.197627 -0.114315 -0.137236 0.101 Uiso 1 1 calc R U . . .
H1B H 0.242902 -0.222955 -0.120849 0.101 Uiso 1 1 calc R U . . .
H1C H 0.339903 -0.126171 -0.135567 0.101 Uiso 1 1 calc R U . . .
C2 C 0.3333(2) 0.00653(17) -0.02003(12) 0.0429(5) Uani 1 1 d . . . . .
C3 C 0.3454(2) 0.07825(19) -0.06901(12) 0.0507(6) Uani 1 1 d . . . . .
H3 H 0.324055 0.052580 -0.118445 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3892(2) 0.18784(18) -0.04478(11) 0.0478(6) Uani 1 1 d . . . . .
H4 H 0.396938 0.236410 -0.077637 0.057 Uiso 1 1 calc R U . . .
C5 C 0.42098(19) 0.22443(16) 0.02801(11) 0.0378(5) Uani 1 1 d . . . . .
C6 C 0.4098(2) 0.15337(18) 0.07735(11) 0.0455(5) Uani 1 1 d . . . . .
H6 H 0.432090 0.179149 0.126741 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3658(2) 0.04460(18) 0.05321(12) 0.0479(6) Uani 1 1 d . . . . .
H7 H 0.357815 -0.003626 0.086267 0.057 Uiso 1 1 calc R U . . .
C8 C 0.58496(19) 0.39532(16) 0.05078(11) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.6768(2) 0.35956(18) 0.01377(12) 0.0462(5) Uani 1 1 d . . . . .
H9 H 0.665453 0.290925 -0.014271 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7854(2) 0.43425(19) 0.02226(13) 0.0494(6) Uani 1 1 d . . . . .
C11 C 0.8053(2) 0.53597(19) 0.06426(13) 0.0522(6) Uani 1 1 d . . . . .
H11 H 0.882256 0.582242 0.068462 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7127(2) 0.56958(18) 0.09991(12) 0.0451(5) Uani 1 1 d . . . . .
H12 H 0.725108 0.637897 0.128453 0.054 Uiso 1 1 calc R U . . .
C13 C 0.60080(19) 0.49770(16) 0.09156(11) 0.0358(5) Uani 1 1 d . . . . .
C14 C 0.40718(19) 0.40680(16) 0.09447(10) 0.0363(5) Uani 1 1 d . . . . .
C15 C 0.28288(19) 0.39146(17) 0.11097(11) 0.0387(5) Uani 1 1 d . . . . .
C16 C 0.1896(2) 0.29920(19) 0.08378(12) 0.0528(6) Uani 1 1 d . . . . .
H16 H 0.206251 0.241703 0.052118 0.063 Uiso 1 1 calc R U . . .
C17 C 0.0761(2) 0.2957(2) 0.10444(13) 0.0604(7) Uani 1 1 d . . . . .
C18 C 0.0456(2) 0.3785(2) 0.15089(14) 0.0608(7) Uani 1 1 d . . . . .
H18 H -0.033668 0.372303 0.164730 0.073 Uiso 1 1 calc R U . . .
C19 C 0.1339(2) 0.4694(2) 0.17598(13) 0.0528(6) Uani 1 1 d . . . . .
H19 H 0.113722 0.526345 0.206562 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2557(2) 0.47963(17) 0.15681(11) 0.0399(5) Uani 1 1 d . . . . .
C21 C 0.4507(2) 0.58901(16) 0.16449(10) 0.0367(5) Uani 1 1 d . . . . .
C22 C 0.5044(2) 0.76572(18) 0.31593(11) 0.0434(5) Uani 1 1 d . . . . .
C23 C 0.4627(2) 0.8438(2) 0.36103(14) 0.0624(7) Uani 1 1 d . . . . .
H23 H 0.433376 0.902402 0.342806 0.075 Uiso 1 1 calc R U . . .
C24 C 0.4646(3) 0.8348(3) 0.43252(16) 0.0794(9) Uani 1 1 d . . . . .
H24 H 0.437206 0.888177 0.462522 0.095 Uiso 1 1 calc R U . . .
C25 C 0.5062(3) 0.7484(3) 0.46100(14) 0.0812(10) Uani 1 1 d . . . . .
C26 C 0.5448(3) 0.6699(3) 0.41490(15) 0.0787(9) Uani 1 1 d . . . . .
H26 H 0.571208 0.609842 0.432733 0.094 Uiso 1 1 calc R U . . .
C27 C 0.5451(2) 0.6785(2) 0.34248(13) 0.0586(6) Uani 1 1 d . . . . .
H27 H 0.572732 0.625433 0.312311 0.070 Uiso 1 1 calc R U . . .
C28 C 0.5137(4) 0.7394(4) 0.54089(17) 0.1367(18) Uani 1 1 d . . . . .
H28A H 0.600187 0.758395 0.564646 0.205 Uiso 1 1 calc R U . . .
H28B H 0.481104 0.665815 0.545867 0.205 Uiso 1 1 calc R U . . .
H28C H 0.464419 0.788216 0.562613 0.205 Uiso 1 1 calc R U . . .
S2 S 0.29958(6) 0.61828(5) 0.71496(3) 0.04702(16) Uani 1 1 d . . . . .
O4 O -0.0565(2) 0.81094(18) 0.15620(10) 0.0929(7) Uani 1 1 d . . . . .
O5 O 0.32996(17) 0.51774(13) 0.73501(9) 0.0602(4) Uani 1 1 d . . . . .
O6 O 0.21542(16) 0.66955(14) 0.75460(9) 0.0623(5) Uani 1 1 d . . . . .
N5 N 0.09446(17) 0.64630(14) 0.40673(9) 0.0415(4) Uani 1 1 d . . . . .
N6 N 0.17147(16) 0.63484(13) 0.51922(9) 0.0378(4) Uani 1 1 d . . . . .
N7 N 0.22629(18) 0.77450(15) 0.61942(10) 0.0481(5) Uani 1 1 d . . . . .
N8 N 0.24781(18) 0.59122(14) 0.62938(9) 0.0462(5) Uani 1 1 d . . . . .
F3 F 0.04441(15) 0.25839(11) 0.32767(8) 0.0751(4) Uani 1 1 d . . . . .
F4 F 0.1393(2) 1.08271(12) 0.44824(10) 0.1036(6) Uani 1 1 d . . . . .
C29 C 0.0254(4) 0.8339(3) 0.10668(16) 0.1095(13) Uani 1 1 d . . . . .
H29A H 0.099817 0.883467 0.131465 0.164 Uiso 1 1 calc R U . . .
H29B H -0.016907 0.866604 0.069047 0.164 Uiso 1 1 calc R U . . .
H29C H 0.048982 0.767416 0.085787 0.164 Uiso 1 1 calc R U . . .
C30 C -0.0119(3) 0.7715(2) 0.21696(13) 0.0576(7) Uani 1 1 d . . . . .
C31 C -0.0997(3) 0.7461(2) 0.26048(14) 0.0677(8) Uani 1 1 d . . . . .
H31 H -0.182269 0.757877 0.247969 0.081 Uiso 1 1 calc R U . . .
C32 C -0.0660(2) 0.7036(2) 0.32210(13) 0.0565(6) Uani 1 1 d . . . . .
H32 H -0.125885 0.684721 0.350832 0.068 Uiso 1 1 calc R U . . .
C33 C 0.0567(2) 0.68892(16) 0.34130(11) 0.0390(5) Uani 1 1 d . . . . .
C34 C 0.1443(2) 0.71433(18) 0.29825(12) 0.0477(6) Uani 1 1 d . . . . .
H34 H 0.227138 0.703762 0.311374 0.057 Uiso 1 1 calc R U . . .
C35 C 0.1102(3) 0.75566(19) 0.23529(13) 0.0543(6) Uani 1 1 d . . . . .
H35 H 0.169517 0.772474 0.205794 0.065 Uiso 1 1 calc R U . . .
C36 C 0.0993(2) 0.53620(16) 0.41031(11) 0.0396(5) Uani 1 1 d . . . . .
C37 C 0.0609(2) 0.44682(18) 0.35600(12) 0.0469(5) Uani 1 1 d . . . . .
H37 H 0.025753 0.452425 0.308994 0.056 Uiso 1 1 calc R U . . .
C38 C 0.0790(2) 0.34939(18) 0.37748(14) 0.0532(6) Uani 1 1 d . . . . .
C39 C 0.1295(2) 0.33848(19) 0.44724(14) 0.0559(6) Uani 1 1 d . . . . .
H39 H 0.139627 0.269830 0.458202 0.067 Uiso 1 1 calc R U . . .
C40 C 0.1645(2) 0.42826(18) 0.50024(13) 0.0485(6) Uani 1 1 d . . . . .
H40 H 0.197751 0.422300 0.547494 0.058 Uiso 1 1 calc R U . . .
C41 C 0.1483(2) 0.52815(16) 0.48030(11) 0.0395(5) Uani 1 1 d . . . . .
C42 C 0.13897(19) 0.70443(16) 0.47308(11) 0.0387(5) Uani 1 1 d . . . . .
C43 C 0.1558(2) 0.81794(17) 0.49911(12) 0.0418(5) Uani 1 1 d . . . . .
C44 C 0.1347(2) 0.89941(18) 0.45594(13) 0.0536(6) Uani 1 1 d . . . . .
H44 H 0.105494 0.881529 0.406367 0.064 Uiso 1 1 calc R U . . .
C45 C 0.1583(3) 1.00340(19) 0.48916(15) 0.0643(7) Uani 1 1 d . . . . .
C46 C 0.2009(3) 1.0356(2) 0.56247(16) 0.0690(8) Uani 1 1 d . . . . .
H46 H 0.216027 1.109111 0.582518 0.083 Uiso 1 1 calc R U . . .
C47 C 0.2202(2) 0.95861(19) 0.60472(14) 0.0608(7) Uani 1 1 d . . . . .
H47 H 0.247202 0.979410 0.654317 0.073 Uiso 1 1 calc R U . . .
C48 C 0.1998(2) 0.84703(17) 0.57438(12) 0.0441(5) Uani 1 1 d . . . . .
C49 C 0.2173(2) 0.67075(18) 0.59422(11) 0.0414(5) Uani 1 1 d . . . . .
C50 C 0.4443(2) 0.70888(18) 0.72607(11) 0.0441(5) Uani 1 1 d . . . . .
C51 C 0.5544(2) 0.66765(19) 0.72341(12) 0.0505(6) Uani 1 1 d . . . . .
H51 H 0.552275 0.592532 0.716673 0.061 Uiso 1 1 calc R U . . .
C52 C 0.6676(3) 0.7370(2) 0.73066(13) 0.0587(6) Uani 1 1 d . . . . .
H52 H 0.741496 0.707981 0.729167 0.070 Uiso 1 1 calc R U . . .
C53 C 0.6739(3) 0.8489(2) 0.74014(13) 0.0595(7) Uani 1 1 d . . . . .
C54 C 0.5628(3) 0.8898(2) 0.74396(12) 0.0573(7) Uani 1 1 d . . . . .
H54 H 0.565395 0.964984 0.751621 0.069 Uiso 1 1 calc R U . . .
C55 C 0.4484(2) 0.82123(19) 0.73661(11) 0.0499(6) Uani 1 1 d . . . . .
H55 H 0.374519 0.850018 0.738711 0.060 Uiso 1 1 calc R U . . .
C56 C 0.7982(3) 0.9248(3) 0.7481(2) 0.1021(11) Uani 1 1 d . . . . .
H56A H 0.854433 0.913334 0.789538 0.153 Uiso 1 1 calc R U . . .
H56B H 0.784235 0.999069 0.754476 0.153 Uiso 1 1 calc R U . . .
H56C H 0.835204 0.910352 0.705419 0.153 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'
F F 0.0171 0.0103 '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
O3 S1 O2 115.71(10) . . ?
O3 S1 N4 114.34(10) . . ?
O2 S1 N4 105.29(9) . . ?
O3 S1 C22 108.02(10) . . ?
O2 S1 C22 105.08(10) . . ?
N4 S1 C22 107.78(10) . . ?
C2 O1 C1 117.01(18) . . ?
C14 N1 C8 108.22(16) . . ?
C14 N1 C5 126.10(17) . . ?
C8 N1 C5 125.14(16) . . ?
C14 N2 C13 108.59(16) . . ?
C14 N2 C21 121.55(17) . . ?
C13 N2 C21 129.85(17) . . ?
C21 N3 C20 120.33(18) . . ?
C21 N4 S1 120.63(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.9(2) . . ?
O1 C2 C3 124.20(19) . . ?
C7 C2 C3 119.9(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.95(19) . . ?
C4 C5 N1 119.99(18) . . ?
C6 C5 N1 119.06(18) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 123.13(19) . . ?
C13 C8 N1 108.37(17) . . ?
C9 C8 N1 128.51(19) . . ?
C10 C9 C8 114.0(2) . . ?
C10 C9 H9 123.0 . . ?
C8 C9 H9 123.0 . . ?
F1 C10 C9 117.8(2) . . ?
F1 C10 C11 118.1(2) . . ?
C9 C10 C11 124.2(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 117.1(2) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C12 C13 C8 120.90(19) . . ?
C12 C13 N2 133.42(19) . . ?
C8 C13 N2 105.66(17) . . ?
N1 C14 N2 109.12(17) . . ?
N1 C14 C15 130.47(18) . . ?
N2 C14 C15 120.39(18) . . ?
C16 C15 C20 120.37(19) . . ?
C16 C15 C14 125.16(19) . . ?
C20 C15 C14 114.44(18) . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 F2 118.2(2) . . ?
C16 C17 C18 123.4(2) . . ?
F2 C17 C18 118.5(2) . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.7(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
N3 C20 C15 124.22(19) . . ?
N3 C20 C19 118.37(19) . . ?
C15 C20 C19 117.41(19) . . ?
N3 C21 N4 128.30(19) . . ?
N3 C21 N2 118.89(18) . . ?
N4 C21 N2 112.82(17) . . ?
C27 C22 C23 119.9(2) . . ?
C27 C22 S1 121.49(17) . . ?
C23 C22 S1 118.43(19) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 117.9(3) . . ?
C24 C25 C28 122.1(3) . . ?
C26 C25 C28 120.0(4) . . ?
C25 C26 C27 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C22 C27 C26 119.4(3) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 S2 O5 116.61(11) . . ?
O6 S2 N8 112.81(10) . . ?
O5 S2 N8 105.20(10) . . ?
O6 S2 C50 108.82(11) . . ?
O5 S2 C50 106.53(11) . . ?
N8 S2 C50 106.23(10) . . ?
C30 O4 C29 119.1(3) . . ?
C42 N5 C36 108.38(17) . . ?
C42 N5 C33 126.72(17) . . ?
C36 N5 C33 124.75(17) . . ?
C42 N6 C41 108.73(16) . . ?
C42 N6 C49 122.41(17) . . ?
C41 N6 C49 128.84(17) . . ?
C49 N7 C48 120.92(18) . . ?
C49 N8 S2 119.27(15) . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O4 C30 C35 124.4(2) . . ?
O4 C30 C31 115.2(2) . . ?
C35 C30 C31 120.4(2) . . ?
C32 C31 C30 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.2(2) . . ?
C34 C33 N5 119.37(19) . . ?
C32 C33 N5 120.41(19) . . ?
C33 C34 C35 120.3(2) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 119.2(2) . . ?
C30 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C41 C36 C37 123.2(2) . . ?
C41 C36 N5 108.00(17) . . ?
C37 C36 N5 128.8(2) . . ?
C38 C37 C36 114.2(2) . . ?
C38 C37 H37 122.9 . . ?
C36 C37 H37 122.9 . . ?
F3 C38 C37 117.8(2) . . ?
F3 C38 C39 118.0(2) . . ?
C37 C38 C39 124.1(2) . . ?
C40 C39 C38 120.4(2) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 117.0(2) . . ?
C39 C40 H40 121.5 . . ?
C41 C40 H40 121.5 . . ?
C36 C41 C40 121.1(2) . . ?
C36 C41 N6 106.19(17) . . ?
C40 C41 N6 132.7(2) . . ?
N5 C42 N6 108.69(17) . . ?
N5 C42 C43 131.61(19) . . ?
N6 C42 C43 119.70(18) . . ?
C48 C43 C44 120.25(19) . . ?
C48 C43 C42 114.48(18) . . ?
C44 C43 C42 125.3(2) . . ?
C45 C44 C43 117.5(2) . . ?
C45 C44 H44 121.3 . . ?
C43 C44 H44 121.3 . . ?
C44 C45 F4 118.1(2) . . ?
C44 C45 C46 124.3(2) . . ?
F4 C45 C46 117.6(2) . . ?
C47 C46 C45 119.0(2) . . ?
C47 C46 H46 120.5 . . ?
C45 C46 H46 120.5 . . ?
C46 C47 C48 120.8(2) . . ?
C46 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
N7 C48 C47 117.7(2) . . ?
N7 C48 C43 124.11(19) . . ?
C47 C48 C43 118.2(2) . . ?
N7 C49 N8 128.6(2) . . ?
N7 C49 N6 118.20(19) . . ?
N8 C49 N6 113.17(18) . . ?
C51 C50 C55 119.5(2) . . ?
C51 C50 S2 119.46(18) . . ?
C55 C50 S2 121.06(18) . . ?
C50 C51 C52 120.2(2) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
C51 C52 C53 121.4(2) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C54 118.0(2) . . ?
C52 C53 C56 121.2(3) . . ?
C54 C53 C56 120.7(3) . . ?
C55 C54 C53 121.3(2) . . ?
C55 C54 H54 119.4 . . ?
C53 C54 H54 119.4 . . ?
C54 C55 C50 119.6(2) . . ?
C54 C55 H55 120.2 . . ?
C50 C55 H55 120.2 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 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 O3 1.4354(16) . ?
S1 O2 1.4357(16) . ?
S1 N4 1.5969(17) . ?
S1 C22 1.772(2) . ?
O1 C2 1.357(2) . ?
O1 C1 1.424(3) . ?
N1 C14 1.350(3) . ?
N1 C8 1.392(3) . ?
N1 C5 1.448(3) . ?
N2 C14 1.353(2) . ?
N2 C13 1.417(2) . ?
N2 C21 1.428(2) . ?
N3 C21 1.305(3) . ?
N3 C20 1.368(3) . ?
N4 C21 1.333(3) . ?
F1 C10 1.356(2) . ?
F2 C17 1.354(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.378(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.380(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.367(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.419(3) . ?
C15 C16 1.404(3) . ?
C15 C20 1.405(3) . ?
C16 C17 1.341(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.412(3) . ?
C19 H19 0.9300 . ?
C22 C27 1.366(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(4) . ?
C25 C28 1.520(4) . ?
C26 C27 1.388(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
S2 O6 1.4320(17) . ?
S2 O5 1.4334(16) . ?
S2 N8 1.6059(18) . ?
S2 C50 1.765(2) . ?
O4 C30 1.363(3) . ?
O4 C29 1.409(4) . ?
N5 C42 1.346(3) . ?
N5 C36 1.400(3) . ?
N5 C33 1.441(3) . ?
N6 C42 1.360(3) . ?
N6 C41 1.407(3) . ?
N6 C49 1.420(3) . ?
N7 C49 1.309(3) . ?
N7 C48 1.359(3) . ?
N8 C49 1.325(3) . ?
F3 C38 1.347(3) . ?
F4 C45 1.360(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C35 1.369(4) . ?
C30 C31 1.377(4) . ?
C31 C32 1.369(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.373(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.368(3) . ?
C34 C35 1.383(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C41 1.374(3) . ?
C36 C37 1.384(3) . ?
C37 C38 1.370(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.384(3) . ?
C39 C40 1.370(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.383(3) . ?
C40 H40 0.9300 . ?
C42 C43 1.419(3) . ?
C43 C48 1.413(3) . ?
C43 C44 1.414(3) . ?
C44 C45 1.341(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.380(4) . ?
C46 C47 1.353(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.412(3) . ?
C47 H47 0.9300 . ?
C50 C51 1.374(3) . ?
C50 C55 1.389(3) . ?
C51 C52 1.374(3) . ?
C51 H51 0.9300 . ?
C52 C53 1.381(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.384(4) . ?
C53 C56 1.507(4) . ?
C54 C55 1.379(3) . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N4 C21 -48.37(19) . . . . ?
O2 S1 N4 C21 -176.49(16) . . . . ?
C22 S1 N4 C21 71.74(18) . . . . ?
C1 O1 C2 C7 -176.1(2) . . . . ?
C1 O1 C2 C3 2.6(3) . . . . ?
O1 C2 C3 C4 -179.1(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 N1 -179.4(2) . . . . ?
C14 N1 C5 C4 115.6(2) . . . . ?
C8 N1 C5 C4 -73.9(3) . . . . ?
C14 N1 C5 C6 -63.7(3) . . . . ?
C8 N1 C5 C6 106.8(2) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
N1 C5 C6 C7 179.0(2) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
O1 C2 C7 C6 178.9(2) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C14 N1 C8 C13 1.9(2) . . . . ?
C5 N1 C8 C13 -170.07(18) . . . . ?
C14 N1 C8 C9 -178.1(2) . . . . ?
C5 N1 C8 C9 10.0(3) . . . . ?
C13 C8 C9 C10 1.0(3) . . . . ?
N1 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 F1 -179.28(19) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
F1 C10 C11 C12 178.8(2) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C8 1.9(3) . . . . ?
C11 C12 C13 N2 -179.8(2) . . . . ?
C9 C8 C13 C12 -2.5(3) . . . . ?
N1 C8 C13 C12 177.60(18) . . . . ?
C9 C8 C13 N2 178.84(19) . . . . ?
N1 C8 C13 N2 -1.1(2) . . . . ?
C14 N2 C13 C12 -178.5(2) . . . . ?
C21 N2 C13 C12 0.9(4) . . . . ?
C14 N2 C13 C8 0.0(2) . . . . ?
C21 N2 C13 C8 179.41(18) . . . . ?
C8 N1 C14 N2 -1.9(2) . . . . ?
C5 N1 C14 N2 169.94(18) . . . . ?
C8 N1 C14 C15 176.2(2) . . . . ?
C5 N1 C14 C15 -12.0(3) . . . . ?
C13 N2 C14 N1 1.2(2) . . . . ?
C21 N2 C14 N1 -178.28(16) . . . . ?
C13 N2 C14 C15 -177.11(17) . . . . ?
C21 N2 C14 C15 3.4(3) . . . . ?
N1 C14 C15 C16 -3.5(4) . . . . ?
N2 C14 C15 C16 174.4(2) . . . . ?
N1 C14 C15 C20 178.3(2) . . . . ?
N2 C14 C15 C20 -3.8(3) . . . . ?
C20 C15 C16 C17 -2.2(3) . . . . ?
C14 C15 C16 C17 179.7(2) . . . . ?
C15 C16 C17 F2 179.9(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
F2 C17 C18 C19 -178.1(2) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C21 N3 C20 C15 3.1(3) . . . . ?
C21 N3 C20 C19 -176.71(19) . . . . ?
C16 C15 C20 N3 -177.6(2) . . . . ?
C14 C15 C20 N3 0.7(3) . . . . ?
C16 C15 C20 C19 2.3(3) . . . . ?
C14 C15 C20 C19 -179.44(19) . . . . ?
C18 C19 C20 N3 179.4(2) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C20 N3 C21 N4 176.8(2) . . . . ?
C20 N3 C21 N2 -3.7(3) . . . . ?
S1 N4 C21 N3 -7.5(3) . . . . ?
S1 N4 C21 N2 173.01(13) . . . . ?
C14 N2 C21 N3 0.5(3) . . . . ?
C13 N2 C21 N3 -178.86(18) . . . . ?
C14 N2 C21 N4 -179.90(17) . . . . ?
C13 N2 C21 N4 0.7(3) . . . . ?
O3 S1 C22 C27 138.39(19) . . . . ?
O2 S1 C22 C27 -97.6(2) . . . . ?
N4 S1 C22 C27 14.4(2) . . . . ?
O3 S1 C22 C23 -46.2(2) . . . . ?
O2 S1 C22 C23 77.8(2) . . . . ?
N4 S1 C22 C23 -170.23(18) . . . . ?
C27 C22 C23 C24 1.3(4) . . . . ?
S1 C22 C23 C24 -174.2(2) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C23 C24 C25 C26 -0.7(5) . . . . ?
C23 C24 C25 C28 177.6(3) . . . . ?
C24 C25 C26 C27 1.6(5) . . . . ?
C28 C25 C26 C27 -176.8(3) . . . . ?
C23 C22 C27 C26 -0.4(4) . . . . ?
S1 C22 C27 C26 174.9(2) . . . . ?
C25 C26 C27 C22 -1.0(4) . . . . ?
O6 S2 N8 C49 55.0(2) . . . . ?
O5 S2 N8 C49 -176.83(17) . . . . ?
C50 S2 N8 C49 -64.11(19) . . . . ?
C29 O4 C30 C35 2.4(4) . . . . ?
C29 O4 C30 C31 -176.9(3) . . . . ?
O4 C30 C31 C32 178.6(2) . . . . ?
C35 C30 C31 C32 -0.7(4) . . . . ?
C30 C31 C32 C33 1.6(4) . . . . ?
C31 C32 C33 C34 -1.5(4) . . . . ?
C31 C32 C33 N5 178.8(2) . . . . ?
C42 N5 C33 C34 90.2(3) . . . . ?
C36 N5 C33 C34 -84.8(3) . . . . ?
C42 N5 C33 C32 -90.0(3) . . . . ?
C36 N5 C33 C32 94.9(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
N5 C33 C34 C35 -179.81(19) . . . . ?
O4 C30 C35 C34 -179.5(2) . . . . ?
C31 C30 C35 C34 -0.3(4) . . . . ?
C33 C34 C35 C30 0.5(3) . . . . ?
C42 N5 C36 C41 -0.3(2) . . . . ?
C33 N5 C36 C41 175.53(19) . . . . ?
C42 N5 C36 C37 178.4(2) . . . . ?
C33 N5 C36 C37 -5.8(3) . . . . ?
C41 C36 C37 C38 -1.7(3) . . . . ?
N5 C36 C37 C38 179.8(2) . . . . ?
C36 C37 C38 F3 -179.81(19) . . . . ?
C36 C37 C38 C39 0.9(3) . . . . ?
F3 C38 C39 C40 -179.0(2) . . . . ?
C37 C38 C39 C40 0.3(4) . . . . ?
C38 C39 C40 C41 -0.7(3) . . . . ?
C37 C36 C41 C40 1.3(3) . . . . ?
N5 C36 C41 C40 -179.89(19) . . . . ?
C37 C36 C41 N6 -178.00(19) . . . . ?
N5 C36 C41 N6 0.8(2) . . . . ?
C39 C40 C41 C36 -0.1(3) . . . . ?
C39 C40 C41 N6 179.0(2) . . . . ?
C42 N6 C41 C36 -1.0(2) . . . . ?
C49 N6 C41 C36 177.27(19) . . . . ?
C42 N6 C41 C40 179.8(2) . . . . ?
C49 N6 C41 C40 -1.9(4) . . . . ?
C36 N5 C42 N6 -0.4(2) . . . . ?
C33 N5 C42 N6 -176.06(18) . . . . ?
C36 N5 C42 C43 179.2(2) . . . . ?
C33 N5 C42 C43 3.5(4) . . . . ?
C41 N6 C42 N5 0.9(2) . . . . ?
C49 N6 C42 N5 -177.56(17) . . . . ?
C41 N6 C42 C43 -178.80(18) . . . . ?
C49 N6 C42 C43 2.8(3) . . . . ?
N5 C42 C43 C48 176.8(2) . . . . ?
N6 C42 C43 C48 -3.6(3) . . . . ?
N5 C42 C43 C44 -4.5(4) . . . . ?
N6 C42 C43 C44 175.1(2) . . . . ?
C48 C43 C44 C45 0.2(3) . . . . ?
C42 C43 C44 C45 -178.4(2) . . . . ?
C43 C44 C45 F4 179.5(2) . . . . ?
C43 C44 C45 C46 -0.5(4) . . . . ?
C44 C45 C46 C47 -0.3(5) . . . . ?
F4 C45 C46 C47 179.7(3) . . . . ?
C45 C46 C47 C48 1.3(4) . . . . ?
C49 N7 C48 C47 -175.6(2) . . . . ?
C49 N7 C48 C43 3.0(3) . . . . ?
C46 C47 C48 N7 177.2(2) . . . . ?
C46 C47 C48 C43 -1.5(4) . . . . ?
C44 C43 C48 N7 -177.9(2) . . . . ?
C42 C43 C48 N7 0.9(3) . . . . ?
C44 C43 C48 C47 0.7(3) . . . . ?
C42 C43 C48 C47 179.5(2) . . . . ?
C48 N7 C49 N8 174.8(2) . . . . ?
C48 N7 C49 N6 -3.9(3) . . . . ?
S2 N8 C49 N7 2.0(3) . . . . ?
S2 N8 C49 N6 -179.23(14) . . . . ?
C42 N6 C49 N7 1.1(3) . . . . ?
C41 N6 C49 N7 -177.0(2) . . . . ?
C42 N6 C49 N8 -177.79(18) . . . . ?
C41 N6 C49 N8 4.1(3) . . . . ?
O6 S2 C50 C51 150.47(17) . . . . ?
O5 S2 C50 C51 24.0(2) . . . . ?
N8 S2 C50 C51 -87.81(19) . . . . ?
O6 S2 C50 C55 -30.3(2) . . . . ?
O5 S2 C50 C55 -156.78(17) . . . . ?
N8 S2 C50 C55 91.43(18) . . . . ?
C55 C50 C51 C52 -0.4(3) . . . . ?
S2 C50 C51 C52 178.84(17) . . . . ?
C50 C51 C52 C53 -0.5(4) . . . . ?
C51 C52 C53 C54 1.6(4) . . . . ?
C51 C52 C53 C56 180.0(3) . . . . ?
C52 C53 C54 C55 -1.7(4) . . . . ?
C56 C53 C54 C55 179.9(2) . . . . ?
C53 C54 C55 C50 0.8(3) . . . . ?
C51 C50 C55 C54 0.3(3) . . . . ?
S2 C50 C55 C54 -178.97(16) . . . . ?
