#------------------------------------------------------------------------------
#$Date: 2024-08-07 01:08:30 +0300 (Wed, 07 Aug 2024) $
#$Revision: 294010 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023154.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023154
loop_
_publ_author_name
'Yennawar, Hemant P.'
'Mal, Tapas K.'
'Olsen, Mark A.'
'Lagalante, Anthony F.'
'Louca, Evelyn M.'
'Gavalis, Aloura D.'
'Silverberg, Lee J.'
_publ_section_title
;
Synthesis and crystal structures of two racemic
2-heteroaryl-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-ones.
;
_journal_coeditor_code TX2086
_journal_issue 'Pt 7'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first 699
_journal_page_last 703
_journal_paper_doi 10.1107/S2056989024005103
_journal_volume 80
_journal_year 2024
_chemical_formula_iupac 'C17 H12 N2 O S2'
_chemical_formula_moiety 'C17 H12 N2 O S2'
_chemical_formula_sum 'C17 H12 N2 O S2'
_chemical_formula_weight 324.41
_chemical_name_systematic
3-Phenyl-2-(thiophen-3-yl)-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_cell_angle_alpha 90
_cell_angle_beta 92.7309(11)
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 9.22549(10)
_cell_length_b 20.8037(2)
_cell_length_c 15.87594(19)
_cell_measurement_reflns_used 9971
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 76.1780
_cell_measurement_theta_min 3.4630
_cell_volume 3043.52(6)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 1.5-ac5-024 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5-ac5-024 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 173(2)
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0321
_diffrn_reflns_av_unetI/netI 0.0301
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 20274
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 76.374
_diffrn_reflns_theta_min 3.505
_diffrn_source 'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu 3.187
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.62844
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_density_diffrn 1.416
_exptl_crystal_description block
_exptl_crystal_F_000 1344
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.198
_refine_diff_density_min -0.319
_refine_ls_extinction_coef 0.00078(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref 1.073
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 435
_refine_ls_number_reflns 6042
_refine_ls_number_restraints 139
_refine_ls_restrained_S_all 1.065
_refine_ls_R_factor_all 0.0447
_refine_ls_R_factor_gt 0.0352
_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/[\s^2^(Fo^2^)+(0.0423P)^2^+0.5556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0910
_refine_ls_wR_factor_ref 0.0962
_reflns_number_gt 4922
_reflns_number_total 6042
_reflns_threshold_expression 'I > 2\s(I)'
_iucr_refine_instructions_details
;
TITL ljs64_auto_a.res in P2(1)/n
ljs64_auto.res
created by SHELXL-2018/3 at 13:53:15 on 14-May-2024
REM Old TITL ljs64_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.136, Rweak 0.016, Alpha 0.019
REM 0.386 for 142 systematic absences, Orientation as input
REM Formula found by SHELXT: C33 N2 O1 S4B
CELL 1.54184 9.225492 20.8037 15.87594 90 92.7309 90
ZERR 8 0.000101 0.000236 0.000186 0 0.0011 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 136 96 16 8 16
EQIV $1 -1+X,+Y,+Z
EQIV $2 1-X,1-Y,1-Z
ISOR 0.01 0.02 C19 C20B C21B S4B C22B
ISOR 0.01 0.02 C19 C20A C21A S4A C22A
SADI 0.04 C19 C21B C19 C21A
RIGU C19 C20B C21B S4B C22B
SADI 0.04 S4B C21B S4A C21A
SADI 0.04 S4B C22B S4A C22A
SADI 0.04 C19 C20B C19 C20A
SADI 0.04 S4B C20B S4A C20A
SADI 0.04 C19 C22B C19 C22A
SADI 0.04 C20B C21B C20A C21A
SADI 0.04 C21B C22B C21A C22A
RIGU C22A S4A C21A C20A C19
SADI 0.04 S4B C19 S4A C19
SIMU C20A C21A S4A C22A
DELU C20A C21A S4A C22A
ISOR 0.001 0.02 C21A
DFIX 1.7 S4A C21A
TEMP 173
L.S. 20
PLAN 2
SIZE 0.15 0.13 0.08
CONF
HTAB C4 O1_$1
HTAB C18 N2_$2
BOND $H
HTAB
fmap 2
acta
REM
REM
REM
WGHT 0.042300 0.555600
EXTI 0.000781
FVAR 3.81691 0.87377
S1 5 0.771550 0.624057 0.511299 11.00000 0.04009 0.03748 =
0.05185 0.00235 -0.00127 -0.00712
S2 5 0.565073 0.853558 0.470592 11.00000 0.05656 0.04596 =
0.06295 0.00287 0.01582 0.00702
O1 4 1.122379 0.765138 0.499999 11.00000 0.04294 0.08163 =
0.05907 -0.00322 0.00598 -0.02849
N1 3 0.937201 0.711640 0.432316 11.00000 0.03058 0.04750 =
0.03723 0.00026 0.00499 -0.00453
N2 3 0.832186 0.637107 0.672923 11.00000 0.05073 0.05517 =
0.04854 0.01204 0.00358 0.00035
C1 1 0.786960 0.690093 0.436296 11.00000 0.03005 0.04219 =
0.03706 -0.00245 0.00060 -0.00472
AFIX 13
H1 2 0.758821 0.672688 0.380531 11.00000 -1.20000
AFIX 0
C2 1 0.682335 0.743696 0.452679 11.00000 0.03241 0.04180 =
0.03071 0.00051 0.00108 -0.00227
C3 1 0.531531 0.732957 0.461301 11.00000 0.03376 0.04883 =
0.05074 0.00320 0.00150 -0.00527
AFIX 43
H3 2 0.488994 0.692420 0.459691 11.00000 -1.20000
AFIX 0
C4 1 0.456089 0.788326 0.472161 11.00000 0.03436 0.06244 =
0.05441 0.00500 0.00686 0.00262
AFIX 43
H4 2 0.356762 0.790048 0.479538 11.00000 -1.20000
AFIX 0
C5 1 0.715109 0.807350 0.456510 11.00000 0.03772 0.04521 =
0.04991 0.00044 0.01004 -0.00282
AFIX 43
H5 2 0.808150 0.823803 0.452003 11.00000 -1.20000
AFIX 0
C6 1 0.862137 0.661428 0.597598 11.00000 0.03345 0.04141 =
0.04349 0.00301 0.00059 0.00184
C7 1 0.900998 0.662943 0.740169 11.00000 0.06290 0.08079 =
0.04164 0.01228 -0.00098 -0.00136
AFIX 43
H7 2 0.883201 0.645858 0.792814 11.00000 -1.20000
AFIX 0
C8 1 0.996913 0.713395 0.736678 11.00000 0.05640 0.09641 =
0.04137 -0.00278 -0.00705 -0.00601
AFIX 43
H8 2 1.039798 0.730783 0.785748 11.00000 -1.20000
AFIX 0
C9 1 1.027751 0.737407 0.659247 11.00000 0.04232 0.07286 =
0.05041 -0.00550 -0.00211 -0.01322
AFIX 43
H9 2 1.092899 0.771252 0.655162 11.00000 -1.20000
AFIX 0
C10 1 0.961285 0.711005 0.586637 11.00000 0.03151 0.05019 =
0.04096 0.00127 -0.00127 -0.00346
C11 1 1.012596 0.732356 0.503602 11.00000 0.03291 0.04819 =
0.04466 -0.00125 0.00042 -0.00615
C12 1 0.997215 0.717824 0.350637 11.00000 0.04124 0.03791 =
0.04146 0.00028 0.01029 -0.00298
C13 1 0.916125 0.743993 0.284099 11.00000 0.05386 0.05006 =
0.04346 0.00021 0.00682 0.00492
AFIX 43
H13 2 0.823682 0.759897 0.292406 11.00000 -1.20000
AFIX 0
C14 1 0.972289 0.746618 0.204801 11.00000 0.08100 0.05681 =
0.04325 0.00409 0.00816 -0.00165
AFIX 43
H14 2 0.917104 0.763988 0.159829 11.00000 -1.20000
AFIX 0
C15 1 1.108814 0.723722 0.192396 11.00000 0.08158 0.05879 =
0.05217 -0.00437 0.03037 -0.01190
AFIX 43
H15 2 1.146461 0.725768 0.139154 11.00000 -1.20000
AFIX 0
C16 1 1.190102 0.697723 0.258716 11.00000 0.05701 0.06079 =
0.07211 -0.00340 0.02955 -0.00194
AFIX 43
H16 2 1.282569 0.682033 0.249955 11.00000 -1.20000
AFIX 0
C17 1 1.135858 0.694632 0.338422 11.00000 0.04349 0.05038 =
0.05750 0.00433 0.01292 0.00003
AFIX 43
H17 2 1.191497 0.677257 0.383208 11.00000 -1.20000
AFIX 0
S3 5 0.624001 0.412083 0.263338 11.00000 0.05978 0.03784 =
0.05461 0.00071 -0.00097 0.00229
PART 1
S4B 5 0.299532 0.506035 0.023550 21.00000 0.06710 0.09138 =
0.05346 0.00806 -0.01008 -0.00057
PART 0
O2 4 0.563547 0.617136 0.307441 11.00000 0.05580 0.03900 =
0.07275 -0.01430 0.01057 -0.00843
N3 3 0.463846 0.517348 0.300550 11.00000 0.04047 0.03890 =
0.04481 -0.00902 0.00682 -0.00801
N4 3 0.855143 0.454289 0.193106 11.00000 0.04567 0.06917 =
0.06063 -0.01251 0.00243 0.00730
C18 1 0.452753 0.455873 0.255906 11.00000 0.04512 0.03670 =
0.04279 -0.00597 0.00573 -0.00910
AFIX 13
H18 2 0.381763 0.429829 0.284727 11.00000 -1.20000
AFIX 0
C19 1 0.397201 0.462339 0.165339 11.00000 0.03690 0.04569 =
0.04610 -0.00489 0.00393 -0.00823
PART 1
C20B 1 0.378719 0.408437 0.109683 21.00000 0.05836 0.05428 =
0.04798 -0.01310 0.00350 -0.01173
AFIX 43
H20B 2 0.400998 0.366169 0.124316 21.00000 -1.20000
AFIX 0
C21B 1 0.324118 0.427465 0.032456 21.00000 0.07192 0.09126 =
0.06066 -0.02519 -0.00101 -0.01450
AFIX 43
H21B 2 0.302562 0.398858 -0.011382 21.00000 -1.20000
AFIX 0
C22B 1 0.358585 0.518136 0.127130 21.00000 0.05631 0.05539 =
0.04633 -0.00144 -0.00487 -0.00248
AFIX 43
H22B 2 0.363219 0.558111 0.153342 21.00000 -1.20000
AFIX 0
PART 0
C23 1 0.732663 0.474049 0.226649 11.00000 0.04174 0.04840 =
0.03889 -0.00411 -0.00207 0.00070
C24 1 0.941654 0.499762 0.164205 11.00000 0.04126 0.09293 =
0.05909 -0.01679 0.00466 -0.00189
AFIX 43
H24 2 1.027172 0.486821 0.140496 11.00000 -1.20000
AFIX 0
C25 1 0.912797 0.564405 0.167144 11.00000 0.04707 0.08330 =
0.05511 -0.00640 0.00892 -0.01832
AFIX 43
H25 2 0.976064 0.594185 0.145228 11.00000 -1.20000
AFIX 0
C26 1 0.786991 0.584040 0.203610 11.00000 0.05137 0.05412 =
0.05075 -0.00192 0.00261 -0.01175
AFIX 43
H26 2 0.765099 0.627564 0.207161 11.00000 -1.20000
AFIX 0
C27 1 0.693609 0.538574 0.234862 11.00000 0.03827 0.04405 =
0.03956 -0.00381 -0.00061 -0.00616
C28 1 0.568380 0.561412 0.282958 11.00000 0.04032 0.04069 =
0.04385 -0.00577 0.00030 -0.00545
C29 1 0.355213 0.532671 0.359508 11.00000 0.03894 0.03849 =
0.04209 -0.00115 0.00405 -0.00099
C30 1 0.395881 0.554445 0.439077 11.00000 0.04960 0.04886 =
0.04542 -0.00250 0.00110 -0.00126
AFIX 43
H30 2 0.493426 0.560768 0.454313 11.00000 -1.20000
AFIX 0
C31 1 0.290725 0.566858 0.496214 11.00000 0.07699 0.05712 =
0.04302 -0.00119 0.01229 0.00571
AFIX 43
H31 2 0.318003 0.581916 0.549804 11.00000 -1.20000
AFIX 0
C32 1 0.146555 0.557169 0.474592 11.00000 0.06644 0.05412 =
0.07126 0.01031 0.02906 0.01088
AFIX 43
H32 2 0.076454 0.565609 0.513315 11.00000 -1.20000
AFIX 0
C33 1 0.106702 0.535075 0.395928 11.00000 0.04163 0.06548 =
0.08243 0.00963 0.01109 0.00144
AFIX 43
H33 2 0.009141 0.528030 0.381416 11.00000 -1.20000
AFIX 0
C34 1 0.210112 0.523045 0.337513 11.00000 0.04395 0.05769 =
0.05467 -0.00138 -0.00050 -0.00490
AFIX 43
H34 2 0.182062 0.508564 0.283761 11.00000 -1.20000
AFIX 0
PART 2
C20A 1 0.356682 0.516863 0.111617 -21.00000 0.06112 0.04737 =
0.06303 0.00354 0.00745 -0.00078
AFIX 43
H20A 2 0.370954 0.559347 0.128254 -21.00000 -1.20000
AFIX 0
C21A 1 0.298111 0.500627 0.037479 -21.00000 0.06412 0.06398 =
0.06416 0.00041 0.00305 -0.00008
AFIX 43
H21A 2 0.250599 0.528811 0.000010 -21.00000 -1.20000
AFIX 0
S4A 5 0.321710 0.420644 0.019916 -21.00000 0.06157 0.06661 =
0.06167 -0.00846 -0.00213 -0.01523
C22A 1 0.366519 0.409359 0.123146 -21.00000 0.05064 0.05238 =
0.05002 -0.00235 0.00734 -0.00637
AFIX 43
H22A 2 0.369269 0.368919 0.148137 -21.00000 -1.20000
AFIX 0
HKLF 4
REM ljs64_auto_a.res in P2(1)/n
REM wR2 = 0.0962, GooF = S = 1.073, Restrained GooF = 1.065 for all data
REM R1 = 0.0352 for 4922 Fo > 4sig(Fo) and 0.0447 for all 6042 data
REM 435 parameters refined using 139 restraints
END
WGHT 0.0419 0.5974
REM Instructions for potential hydrogen bonds
HTAB C1 O2
HTAB C4 O1_$1
HTAB C18 N2_$2
HTAB C30 S1
EQIV $3 x-1/2, -y+3/2, z-1/2
HTAB C21A S2_$3
REM Highest difference peak 0.198, deepest hole -0.319, 1-sigma level 0.038
Q1 1 0.3156 0.5446 0.0376 11.00000 0.05 0.20
Q2 1 0.8682 0.6971 0.4375 11.00000 0.05 0.19
REM The information below was added by Olex2.
REM
REM R1 = 0.0352 for 4922 Fo > 4sig(Fo) and 0.0447 for all 20728 data
REM 435 parameters refined using n/a restraints
REM Highest difference peak 0.20, deepest hole -0.32
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0447
REM R1_gt = 0.0352
REM wR_ref = 0.0962
REM GOOF = 1.073
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 20728
REM Reflections_gt = 4922
REM Parameters = 435
REM Hole = -0.32
REM Peak = 0.20
REM Flack = n/a
;
_cod_data_source_file tx2086.cif
_cod_data_source_block 1
_cod_depositor_comments
'Adding full bibliography for 2023154--2023155.cif.'
_cod_database_code 2023154
_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 0.646
_shelx_estimated_absorpt_t_max 0.785
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.77155(5) 0.62406(2) 0.51130(3) 0.04325(12) Uani d 1 . .
S S2 0.56507(6) 0.85356(2) 0.47059(3) 0.05474(14) Uani d 1 . .
O O1 1.12238(14) 0.76514(8) 0.50000(9) 0.0611(4) Uani d 1 . .
N N1 0.93720(14) 0.71164(7) 0.43232(9) 0.0383(3) Uani d 1 . .
N N2 0.83219(17) 0.63711(8) 0.67292(10) 0.0514(4) Uani d 1 . .
C C1 0.78696(17) 0.69009(8) 0.43630(11) 0.0365(4) Uani d 1 . .
H H1 0.758821 0.672688 0.380531 0.044 Uiso calc 1 . .
C C2 0.68234(17) 0.74370(8) 0.45268(10) 0.0350(3) Uani d 1 . .
C C3 0.53153(18) 0.73296(9) 0.46130(12) 0.0445(4) Uani d 1 . .
H H3 0.488994 0.692420 0.459691 0.053 Uiso calc 1 . .
C C4 0.4561(2) 0.78833(10) 0.47216(13) 0.0503(5) Uani d 1 . .
H H4 0.356762 0.790048 0.479538 0.060 Uiso calc 1 . .
C C5 0.71511(19) 0.80735(9) 0.45651(12) 0.0440(4) Uani d 1 . .
H H5 0.808150 0.823803 0.452003 0.053 Uiso calc 1 . .
C C6 0.86214(18) 0.66143(8) 0.59760(11) 0.0395(4) Uani d 1 . .
C C7 0.9010(2) 0.66294(12) 0.74017(13) 0.0619(6) Uani d 1 . .
H H7 0.883201 0.645858 0.792814 0.074 Uiso calc 1 . .
C C8 0.9969(2) 0.71339(13) 0.73668(13) 0.0650(6) Uani d 1 . .
H H8 1.039798 0.730783 0.785748 0.078 Uiso calc 1 . .
C C9 1.0278(2) 0.73741(11) 0.65925(13) 0.0553(5) Uani d 1 . .
H H9 1.092899 0.771252 0.655162 0.066 Uiso calc 1 . .
C C10 0.96128(17) 0.71101(9) 0.58664(11) 0.0410(4) Uani d 1 . .
C C11 1.01260(18) 0.73236(9) 0.50360(11) 0.0420(4) Uani d 1 . .
C C12 0.99721(18) 0.71782(8) 0.35064(11) 0.0399(4) Uani d 1 . .
C C13 0.9161(2) 0.74399(9) 0.28410(12) 0.0490(4) Uani d 1 . .
H H13 0.823682 0.759897 0.292406 0.059 Uiso calc 1 . .
C C14 0.9723(3) 0.74662(10) 0.20480(13) 0.0602(5) Uani d 1 . .
H H14 0.917104 0.763988 0.159829 0.072 Uiso calc 1 . .
C C15 1.1088(3) 0.72372(11) 0.19240(14) 0.0633(6) Uani d 1 . .
H H15 1.146461 0.725768 0.139154 0.076 Uiso calc 1 . .
C C16 1.1901(3) 0.69772(11) 0.25872(15) 0.0625(6) Uani d 1 . .
H H16 1.282569 0.682033 0.249955 0.075 Uiso calc 1 . .
C C17 1.1359(2) 0.69463(9) 0.33842(13) 0.0501(5) Uani d 1 . .
H H17 1.191497 0.677257 0.383208 0.060 Uiso calc 1 . .
S S3 0.62400(6) 0.41208(2) 0.26334(3) 0.05086(14) Uani d 1 . .
S S4B 0.2995(2) 0.50603(6) 0.02355(7) 0.0711(3) Uani d 0.874(3) A 1
O O2 0.56355(15) 0.61714(6) 0.30744(9) 0.0556(4) Uani d 1 . .
N N3 0.46385(15) 0.51735(7) 0.30055(9) 0.0412(3) Uani d 1 . .
N N4 0.85514(18) 0.45429(9) 0.19311(11) 0.0585(4) Uani d 1 . .
C C18 0.45275(19) 0.45587(8) 0.25591(11) 0.0414(4) Uani d 1 . .
H H18 0.381763 0.429829 0.284727 0.050 Uiso calc 1 . .
C C19 0.39720(18) 0.46234(9) 0.16534(11) 0.0428(4) Uani d 1 . .
C C20B 0.3787(10) 0.4084(3) 0.1097(3) 0.0535(12) Uani d 0.874(3) A 1
H H20B 0.400998 0.366169 0.124316 0.064 Uiso calc 0.874(3) A 1
C C21B 0.3241(12) 0.4275(5) 0.0325(6) 0.075(3) Uani d 0.874(3) A 1
H H21B 0.302562 0.398858 -0.011382 0.090 Uiso calc 0.874(3) A 1
C C22B 0.3586(10) 0.5181(2) 0.1271(3) 0.0529(10) Uani d 0.874(3) A 1
H H22B 0.363219 0.558111 0.153342 0.063 Uiso calc 0.874(3) A 1
C C23 0.73266(19) 0.47405(9) 0.22665(11) 0.0431(4) Uani d 1 . .
C C24 0.9417(2) 0.49976(13) 0.16421(14) 0.0644(6) Uani d 1 . .
H H24 1.027172 0.486821 0.140496 0.077 Uiso calc 1 . .
C C25 0.9128(2) 0.56440(12) 0.16714(13) 0.0616(6) Uani d 1 . .
H H25 0.976064 0.594185 0.145228 0.074 Uiso calc 1 . .
C C26 0.7870(2) 0.58404(10) 0.20361(12) 0.0521(5) Uani d 1 . .
H H26 0.765099 0.627564 0.207161 0.062 Uiso calc 1 . .
C C27 0.69361(18) 0.53857(8) 0.23486(11) 0.0407(4) Uani d 1 . .
C C28 0.56838(18) 0.56141(8) 0.28296(11) 0.0417(4) Uani d 1 . .
C C29 0.35521(18) 0.53267(8) 0.35951(11) 0.0398(4) Uani d 1 . .
C C30 0.3959(2) 0.55445(9) 0.43908(12) 0.0480(4) Uani d 1 . .
H H30 0.493426 0.560768 0.454313 0.058 Uiso calc 1 . .
C C31 0.2907(3) 0.56686(10) 0.49621(13) 0.0587(5) Uani d 1 . .
H H31 0.318003 0.581916 0.549804 0.070 Uiso calc 1 . .
C C32 0.1466(3) 0.55717(11) 0.47459(15) 0.0631(6) Uani d 1 . .
H H32 0.076454 0.565609 0.513315 0.076 Uiso calc 1 . .
C C33 0.1067(2) 0.53507(11) 0.39593(16) 0.0629(6) Uani d 1 . .
H H33 0.009141 0.528030 0.381416 0.076 Uiso calc 1 . .
C C34 0.2101(2) 0.52305(10) 0.33751(13) 0.0522(5) Uani d 1 . .
H H34 0.182062 0.508564 0.283761 0.063 Uiso calc 1 . .
C C20A 0.357(7) 0.5169(16) 0.112(2) 0.057(6) Uani d 0.126(3) A 2
H H20A 0.370954 0.559347 0.128254 0.068 Uiso calc 0.126(3) A 2
C C21A 0.298(6) 0.5006(12) 0.037(2) 0.064(5) Uani d 0.126(3) A 2
H H21A 0.250599 0.528811 0.000010 0.077 Uiso calc 0.126(3) A 2
S S4A 0.322(2) 0.4206(8) 0.0199(10) 0.063(3) Uani d 0.126(3) A 2
C C22A 0.367(7) 0.4094(17) 0.123(2) 0.051(5) Uani d 0.126(3) A 2
H H22A 0.369269 0.368919 0.148137 0.061 Uiso calc 0.126(3) A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0401(2) 0.0375(2) 0.0518(3) -0.00712(17) -0.00127(19) 0.00235(19)
S2 0.0566(3) 0.0460(3) 0.0630(3) 0.0070(2) 0.0158(2) 0.0029(2)
O1 0.0429(7) 0.0816(10) 0.0591(8) -0.0285(7) 0.0060(6) -0.0032(8)
N1 0.0306(7) 0.0475(8) 0.0372(7) -0.0045(6) 0.0050(6) 0.0003(6)
N2 0.0507(9) 0.0552(9) 0.0485(9) 0.0004(7) 0.0036(8) 0.0120(8)
C1 0.0301(8) 0.0422(9) 0.0371(9) -0.0047(7) 0.0006(7) -0.0024(7)
C2 0.0324(8) 0.0418(9) 0.0307(8) -0.0023(7) 0.0011(6) 0.0005(7)
C3 0.0338(8) 0.0488(10) 0.0507(11) -0.0053(7) 0.0015(8) 0.0032(8)
C4 0.0344(9) 0.0624(12) 0.0544(11) 0.0026(8) 0.0069(8) 0.0050(10)
C5 0.0377(9) 0.0452(10) 0.0499(11) -0.0028(7) 0.0100(8) 0.0004(8)
C6 0.0334(8) 0.0414(9) 0.0435(10) 0.0018(7) 0.0006(7) 0.0030(8)
C7 0.0629(13) 0.0808(15) 0.0416(11) -0.0014(11) -0.0010(10) 0.0123(11)
C8 0.0564(12) 0.0964(18) 0.0414(11) -0.0060(12) -0.0071(10) -0.0028(11)
C9 0.0423(10) 0.0729(14) 0.0504(11) -0.0132(9) -0.0021(9) -0.0055(10)
C10 0.0315(8) 0.0502(10) 0.0410(9) -0.0035(7) -0.0013(7) 0.0013(8)
C11 0.0329(8) 0.0482(10) 0.0447(10) -0.0062(7) 0.0004(7) -0.0013(8)
C12 0.0412(9) 0.0379(9) 0.0415(9) -0.0030(7) 0.0103(8) 0.0003(7)
C13 0.0539(11) 0.0501(10) 0.0435(10) 0.0049(9) 0.0068(9) 0.0002(8)
C14 0.0810(15) 0.0568(12) 0.0433(11) -0.0016(11) 0.0082(10) 0.0041(9)
C15 0.0816(16) 0.0588(13) 0.0522(12) -0.0119(11) 0.0304(12) -0.0044(10)
C16 0.0570(12) 0.0608(13) 0.0721(15) -0.0019(10) 0.0295(11) -0.0034(11)
C17 0.0435(10) 0.0504(11) 0.0575(12) 0.0000(8) 0.0129(9) 0.0043(9)
S3 0.0598(3) 0.0378(2) 0.0546(3) 0.0023(2) -0.0010(2) 0.0007(2)
S4B 0.0671(5) 0.0914(6) 0.0535(5) -0.0006(4) -0.0101(5) 0.0081(4)
O2 0.0558(8) 0.0390(7) 0.0727(9) -0.0084(6) 0.0106(7) -0.0143(6)
N3 0.0405(8) 0.0389(7) 0.0448(8) -0.0080(6) 0.0068(6) -0.0090(6)
N4 0.0457(9) 0.0692(11) 0.0606(11) 0.0073(8) 0.0024(8) -0.0125(9)
C18 0.0451(9) 0.0367(9) 0.0428(10) -0.0091(7) 0.0057(8) -0.0060(7)
C19 0.0369(9) 0.0457(9) 0.0461(10) -0.0082(7) 0.0039(8) -0.0049(8)
C20B 0.058(3) 0.0543(15) 0.0480(19) -0.0117(14) 0.003(2) -0.0131(14)
C21B 0.072(4) 0.091(4) 0.061(3) -0.014(3) -0.001(2) -0.025(2)
C22B 0.0563(18) 0.0554(16) 0.046(2) -0.0025(14) -0.005(2) -0.0014(14)
C23 0.0417(9) 0.0484(10) 0.0389(9) 0.0007(8) -0.0021(8) -0.0041(8)
C24 0.0413(11) 0.0929(18) 0.0591(13) -0.0019(11) 0.0047(10) -0.0168(13)
C25 0.0471(11) 0.0833(16) 0.0551(12) -0.0183(11) 0.0089(10) -0.0064(11)
C26 0.0514(11) 0.0541(11) 0.0508(11) -0.0117(9) 0.0026(9) -0.0019(9)
C27 0.0383(9) 0.0440(9) 0.0396(9) -0.0062(7) -0.0006(7) -0.0038(8)
C28 0.0403(9) 0.0407(9) 0.0439(10) -0.0054(7) 0.0003(8) -0.0058(8)
C29 0.0389(9) 0.0385(9) 0.0421(9) -0.0010(7) 0.0041(7) -0.0011(7)
C30 0.0496(10) 0.0489(10) 0.0454(10) -0.0013(8) 0.0011(9) -0.0025(9)
C31 0.0770(15) 0.0571(12) 0.0430(11) 0.0057(11) 0.0123(10) -0.0012(9)
C32 0.0664(14) 0.0541(12) 0.0713(15) 0.0109(10) 0.0291(12) 0.0103(11)
C33 0.0416(11) 0.0655(14) 0.0824(16) 0.0014(9) 0.0111(11) 0.0096(12)
C34 0.0440(10) 0.0577(12) 0.0547(12) -0.0049(9) -0.0005(9) -0.0014(10)
C20A 0.061(11) 0.047(7) 0.063(8) -0.001(7) 0.007(7) 0.004(5)
C21A 0.064(5) 0.064(5) 0.064(5) -0.0001(10) 0.0031(10) 0.0004(10)
S4A 0.062(5) 0.067(4) 0.062(5) -0.015(3) -0.002(3) -0.008(4)
C22A 0.051(10) 0.052(6) 0.050(7) -0.006(6) 0.007(8) -0.002(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_refln_index_h
_diffrn_refln_index_k
_diffrn_refln_index_l
0 0 1
0 0 -2
0 0 -2
0 0 -2
0 0 -2
0 0 2
0 0 -3
0 0 -3
0 0 -3
0 0 3
0 0 -3
0 0 -4
0 0 -4
0 0 -4
0 0 -5
0 0 -5
0 0 -5
0 0 -5
0 0 5
0 0 -6
0 0 -6
0 0 -6
0 0 -6
0 0 6
0 0 7
0 0 -7
0 0 -8
0 0 -8
0 0 -9
0 0 -9
0 0 -9
0 0 -9
0 0 -10
0 0 -10
0 0 -10
0 0 -11
0 0 -11
0 0 -11
0 0 -11
0 0 -12
0 0 -12
0 0 -12
0 0 -12
0 0 -12
0 0 -13
0 0 -13
0 0 -13
0 0 -14
0 0 -14
0 0 -14
0 0 -15
0 0 -15
0 0 -15
0 0 -16
0 0 -17
0 0 -17
0 0 -18
0 0 -18
0 0 -19
0 1 1
0 -1 -1
0 -1 -1
0 1 -1
0 1 -1
0 -1 -1
0 -1 -1
0 1 1
0 1 1
0 -1 -1
0 -1 -1
0 1 -1
0 -1 -1
0 1 1
0 -1 1
0 -1 -2
0 -1 -2
0 1 -2
0 -1 -2
0 1 -2
0 -1 -2
0 -1 -2
0 1 -2
0 -1 -2
0 -1 -3
0 -1 -3
0 1 -3
0 -1 -3
0 1 -3
0 -1 -3
0 1 -3
0 -1 -3
0 1 4
0 -1 4
0 -1 -4
0 1 -4
0 -1 -4
0 1 -4
0 -1 -4
0 1 -4
0 -1 -4
0 1 -4
0 1 -5
0 1 -5
0 -1 -5
0 -1 -5
0 1 -5
0 -1 -5
0 -1 5
0 1 5
0 1 -5
0 -1 -5
0 -1 -6
0 1 -6
0 -1 -6
0 -1 6
0 1 6
0 1 -6
0 -1 -6
0 1 -6
0 -1 -6
0 -1 -6
0 -1 -7
0 -1 7
0 -1 -7
0 1 -7
0 1 -7
0 -1 -7
0 -1 -8
0 1 -8
0 -1 -8
0 1 -8
0 -1 8
0 -1 -9
0 1 -9
0 -1 -9
0 -1 -9
0 1 -9
0 1 -9
0 -1 -9
0 -1 -10
0 1 -10
0 1 -10
0 -1 -10
0 1 -10
0 -1 -10
0 -1 -11
0 -1 -11
0 1 -11
0 -1 -11
0 1 -11
0 -1 -11
0 1 -11
0 -1 -11
0 1 -11
0 -1 -12
0 -1 -12
0 1 -12
0 -1 -12
0 1 -12
0 -1 -12
0 1 -12
0 -1 -12
0 1 -12
0 1 -13
0 -1 -13
0 -1 -13
0 -1 -13
0 1 -13
0 1 -13
0 -1 -13
0 1 -13
0 -1 -13
0 -1 -14
0 -1 -14
0 1 -14
0 1 -14
0 -1 -14
0 1 -14
0 -1 -15
0 -1 -15
0 1 -15
0 1 -15
0 -1 -15
0 1 -15
0 -1 -16
0 1 -16
0 -1 -17
0 1 -17
0 1 -17
0 -1 -17
0 1 -18
0 -1 -18
0 1 -18
0 1 -19
0 2 0
0 -2 0
0 2 0
0 -2 -1
0 2 -1
0 -2 -1
0 -2 -1
0 2 -1
0 -2 -1
0 -2 -1
0 -2 -1
0 -2 -2
0 -2 -2
0 -2 -2
0 -2 -2
0 -2 -2
0 -2 2
0 -2 -2
0 2 -2
0 -2 -2
0 2 -2
0 -2 -2
0 -2 -3
0 -2 -3
0 -2 -3
0 2 -3
0 -2 -3
0 -2 -3
0 2 -3
0 -2 -3
0 2 -3
0 -2 -4
0 -2 -4
0 -2 -4
0 2 -4
0 -2 -4
0 2 -4
0 -2 -4
0 -2 -4
0 -2 -5
0 2 -5
0 -2 -5
0 2 -5
0 -2 5
0 -2 -5
0 2 -5
0 -2 -5
0 -2 -5
0 -2 -6
0 2 -6
0 -2 -6
0 2 6
0 2 -6
0 -2 6
0 -2 -6
0 2 -6
0 -2 -6
0 -2 -6
0 -2 -7
0 -2 -7
0 -2 7
0 2 -7
0 -2 -7
0 2 -7
0 2 7
0 -2 -7
0 -2 -7
0 2 -8
0 -2 -8
0 2 -8
0 -2 -8
0 2 -8
0 -2 8
0 -2 -8
0 2 -9
0 -2 -9
0 -2 -9
0 -2 -9
0 2 -9
0 -2 -9
0 -2 -9
0 2 -10
0 2 -10
0 -2 -10
0 -2 -10
0 -2 -10
0 -2 -10
0 2 -10
0 -2 -10
0 2 -11
0 -2 -11
0 2 -11
0 -2 -11
0 -2 -11
0 2 -11
0 -2 -11
0 2 -11
0 -2 -11
0 2 -12
0 -2 -12
0 2 -12
0 -2 -12
0 -2 -12
0 -2 -12
0 2 -12
0 -2 -12
0 2 -13
0 -2 -13
0 2 -13
0 -2 -13
0 -2 -13
0 2 -13
0 -2 -13
0 2 -14
0 2 -14
0 -2 -14
0 -2 -14
0 2 -14
0 -2 -14
0 2 -15
0 -2 -15
0 -2 -15
0 2 -15
0 -2 -15
0 -2 -16
0 2 -16
0 2 -17
0 -2 -17
0 2 -17
0 -2 -17
0 2 -18
0 -2 -18
0 2 -18
0 2 -19
0 3 0
0 3 0
0 -3 -1
0 -3 -1
0 3 -1
0 3 1
0 -3 -1
0 -3 -2
0 -3 -2
0 -3 -2
0 -3 2
0 -3 -2
0 -3 -2
0 3 -2
0 -3 -2
0 3 -2
0 3 2
0 -3 -2
0 -3 -3
0 -3 -3
0 3 -3
0 3 -3
0 -3 -3
0 -3 -3
0 -3 -3
0 -3 -3
0 -3 -3
0 -3 -3
0 -3 -4
0 -3 -4
0 3 -4
0 -3 -4
0 -3 -4
0 3 -4
0 -3 -4
0 -3 -4
0 -3 -4
0 3 -4
0 -3 -5
0 -3 -5
0 3 -5
0 -3 -5
0 -3 -5
0 -3 -5
0 -3 -5
0 -3 -5
0 3 -5
0 -3 -6
0 -3 -6
0 3 -6
0 -3 -6
0 -3 6
0 -3 -6
0 3 -6
0 3 -6
0 -3 -7
0 3 -7
0 -3 -7
0 -3 -7
0 -3 -7
0 3 -7
0 -3 -7
0 -3 7
0 -3 8
0 -3 -8
0 3 -8
0 3 -8
0 3 -8
0 -3 -8
0 -3 -8
0 -3 -8
0 -3 -8
0 3 -9
0 -3 9
0 -3 -9
0 -3 -9
0 -3 -9
0 3 -9
0 -3 -9
0 -3 -10
0 3 -10
0 -3 -10
0 3 -10
0 -3 -10
0 -3 -10
0 -3 -10
0 3 -11
0 -3 -11
0 -3 -11
0 -3 -11
0 3 -11
0 -3 -11
0 -3 -11
0 -3 -12
0 3 -12
0 -3 -12
0 -3 -12
0 -3 -12
0 3 -12
0 -3 -12
0 3 -12
0 -3 -13
0 3 -13
0 -3 -13
0 -3 -13
0 3 -13
0 3 -13
0 -3 -13
0 -3 -14
0 3 -14
0 -3 -14
0 3 -14
0 -3 -14
0 3 -15
0 -3 -15
0 3 -15
0 -3 -15
0 3 -16
0 -3 -16
0 3 -17
0 -3 -17
0 3 -18
0 3 -18
0 3 -19
0 -4 0
0 4 0
0 -4 -1
0 -4 -1
0 4 -1
0 4 1
0 -4 -2
0 4 -2
0 4 2
0 4 -2
0 -4 -2
0 -4 -2
0 -4 -2
0 -4 -2
0 -4 -2
0 -4 -3
0 4 -3
0 -4 -3
0 -4 -3
0 -4 -3
0 4 -3
0 4 3
0 -4 -3
0 -4 3
0 -4 -3
0 -4 -3
0 -4 -3
0 -4 -4
0 -4 -4
0 -4 -4
0 4 4
0 4 -4
0 4 -4
0 -4 -4
0 4 -4
0 -4 -4
0 -4 -4
0 -4 -4
0 -4 -5
0 -4 -5
0 4 -5
0 -4 -5
0 -4 -5
0 -4 -5
0 4 5
0 -4 -5
0 -4 -5
0 4 -5
0 4 -6
0 -4 -6
0 -4 6
0 -4 -6
0 -4 -6
0 -4 -6
0 4 -6
0 -4 7
0 -4 -7
0 4 -7
0 -4 -7
0 4 -7
0 -4 -7
0 4 -7
0 -4 -7
0 -4 8
0 -4 -8
0 -4 -8
0 4 -8
0 -4 -8
0 4 -8
0 4 -8
0 -4 -9
0 -4 -9
0 -4 9
0 4 -9
0 -4 -9
0 -4 -9
0 -4 -10
0 -4 -10
0 4 -10
0 -4 -10
0 -4 -10
0 -4 -10
0 -4 -11
0 -4 -11
0 -4 -11
0 4 -11
0 -4 -11
0 -4 -11
0 -4 12
0 -4 -12
0 -4 -12
0 -4 -12
0 4 -12
0 -4 -12
0 4 -12
0 -4 -12
0 4 -13
0 -4 -13
0 4 -13
0 -4 -13
0 -4 -13
0 -4 -13
0 4 -14
0 -4 -14
0 -4 -14
0 -4 -14
0 -4 -15
0 4 -15
0 4 -16
0 -4 -16
0 -4 -17
0 4 -17
0 4 -17
0 4 -18
0 4 -18
0 4 -19
0 5 0
0 -5 0
0 5 1
0 5 -1
0 -5 -1
0 -5 -1
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11 4 4
-11 4 -4
11 -5 -6
11 -5 -5
11 -5 -4
11 -5 -3
11 5 -2
-11 5 1
11 5 -1
-11 5 0
11 5 0
11 5 1
-11 5 -1
11 5 1
11 5 2
-11 5 -2
11 5 3
-11 5 -3
-11 5 -4
11 -6 -5
11 -6 -4
11 -6 -3
11 -6 -2
-11 6 1
-11 6 0
11 6 1
-11 6 -1
11 6 2
-11 6 -2
-11 6 -3
11 -7 -4
11 -7 -3
11 -7 -2
11 -7 -1
-11 7 0
-11 7 -1
-11 7 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C1 . . 97.29(8) ?
C4 S2 C5 . . 92.08(9) ?
C11 N1 C1 . . 120.42(14) ?
C11 N1 C12 . . 120.95(14) ?
C12 N1 C1 . . 118.21(13) ?
C7 N2 C6 . . 116.96(18) ?
S1 C1 H1 . . 106.6 ?
N1 C1 S1 . . 111.23(11) ?
N1 C1 H1 . . 106.6 ?
N1 C1 C2 . . 113.43(13) ?
C2 C1 S1 . . 111.94(11) ?
C2 C1 H1 . . 106.6 ?
C3 C2 C1 . . 122.58(15) ?
C5 C2 C1 . . 125.90(15) ?
C5 C2 C3 . . 111.43(16) ?
C2 C3 H3 . . 123.6 ?
C4 C3 C2 . . 112.82(16) ?
C4 C3 H3 . . 123.6 ?
S2 C4 H4 . . 124.2 ?
C3 C4 S2 . . 111.69(14) ?
C3 C4 H4 . . 124.2 ?
S2 C5 H5 . . 124.0 ?
C2 C5 S2 . . 111.97(13) ?
C2 C5 H5 . . 124.0 ?
N2 C6 S1 . . 114.80(13) ?
N2 C6 C10 . . 123.72(16) ?
C10 C6 S1 . . 121.44(13) ?
N2 C7 H7 . . 118.0 ?
N2 C7 C8 . . 124.0(2) ?
C8 C7 H7 . . 118.0 ?
C7 C8 H8 . . 120.8 ?
C9 C8 C7 . . 118.4(2) ?
C9 C8 H8 . . 120.8 ?
C8 C9 H9 . . 120.1 ?
C8 C9 C10 . . 119.81(19) ?
C10 C9 H9 . . 120.1 ?
C6 C10 C11 . . 124.67(16) ?
C9 C10 C6 . . 116.99(17) ?
C9 C10 C11 . . 117.97(16) ?
O1 C11 N1 . . 121.69(17) ?
O1 C11 C10 . . 120.39(16) ?
N1 C11 C10 . . 117.86(14) ?
C13 C12 N1 . . 120.53(15) ?
C13 C12 C17 . . 120.02(17) ?
C17 C12 N1 . . 119.39(16) ?
C12 C13 H13 . . 120.0 ?
C12 C13 C14 . . 119.98(19) ?
C14 C13 H13 . . 120.0 ?
C13 C14 H14 . . 119.9 ?
C15 C14 C13 . . 120.2(2) ?
C15 C14 H14 . . 119.9 ?
C14 C15 H15 . . 120.0 ?
C14 C15 C16 . . 119.9(2) ?
C16 C15 H15 . . 120.0 ?
C15 C16 H16 . . 119.6 ?
C15 C16 C17 . . 120.7(2) ?
C17 C16 H16 . . 119.6 ?
C12 C17 H17 . . 120.4 ?
C16 C17 C12 . . 119.1(2) ?
C16 C17 H17 . . 120.4 ?
C23 S3 C18 . . 96.82(8) ?
C21B S4B C22B . . 91.5(3) ?
C28 N3 C18 . . 121.34(14) ?
C28 N3 C29 . . 120.23(14) ?
C29 N3 C18 . . 118.28(13) ?
C24 N4 C23 . . 116.76(19) ?
S3 C18 H18 . . 106.9 ?
N3 C18 S3 . . 111.41(12) ?
N3 C18 H18 . . 106.9 ?
N3 C18 C19 . . 113.34(15) ?
C19 C18 S3 . . 111.11(12) ?
C19 C18 H18 . . 106.9 ?
C20B C19 C18 . . 122.9(3) ?
C22B C19 C18 . . 125.1(2) ?
C22B C19 C20B . . 112.0(3) ?
C20A C19 C18 . . 133.9(13) ?
C22A C19 C18 . . 117.8(14) ?
C22A C19 C20A . . 108.2(19) ?
C19 C20B H20B . . 124.6 ?
C21B C20B C19 . . 110.8(6) ?
C21B C20B H20B . . 124.6 ?
S4B C21B H21B . . 123.0 ?
C20B C21B S4B . . 114.0(6) ?
C20B C21B H21B . . 123.0 ?
S4B C22B H22B . . 124.2 ?
C19 C22B S4B . . 111.6(3) ?
C19 C22B H22B . . 124.2 ?
N4 C23 S3 . . 114.50(15) ?
N4 C23 C27 . . 124.00(18) ?
C27 C23 S3 . . 121.48(14) ?
N4 C24 H24 . . 117.9 ?
N4 C24 C25 . . 124.3(2) ?
C25 C24 H24 . . 117.9 ?
C24 C25 H25 . . 120.9 ?
C24 C25 C26 . . 118.1(2) ?
C26 C25 H25 . . 120.9 ?
C25 C26 H26 . . 120.1 ?
C25 C26 C27 . . 119.7(2) ?
C27 C26 H26 . . 120.1 ?
C23 C27 C28 . . 124.25(16) ?
C26 C27 C23 . . 117.02(17) ?
C26 C27 C28 . . 118.36(17) ?
O2 C28 N3 . . 122.19(17) ?
O2 C28 C27 . . 120.31(16) ?
N3 C28 C27 . . 117.47(15) ?
C30 C29 N3 . . 120.11(15) ?
C30 C29 C34 . . 119.85(17) ?
C34 C29 N3 . . 119.98(16) ?
C29 C30 H30 . . 120.2 ?
C29 C30 C31 . . 119.59(18) ?
C31 C30 H30 . . 120.2 ?
C30 C31 H31 . . 119.7 ?
C32 C31 C30 . . 120.7(2) ?
C32 C31 H31 . . 119.7 ?
C31 C32 H32 . . 120.2 ?
C33 C32 C31 . . 119.6(2) ?
C33 C32 H32 . . 120.2 ?
C32 C33 H33 . . 119.7 ?
C32 C33 C34 . . 120.6(2) ?
C34 C33 H33 . . 119.7 ?
C29 C34 C33 . . 119.65(19) ?
C29 C34 H34 . . 120.2 ?
C33 C34 H34 . . 120.2 ?
C19 C20A H20A . . 123.0 ?
C21A C20A C19 . . 114(2) ?
C21A C20A H20A . . 123.0 ?
C20A C21A H21A . . 124.8 ?
C20A C21A S4A . . 110(2) ?
S4A C21A H21A . . 124.8 ?
C22A S4A C21A . . 90.2(16) ?
C19 C22A S4A . . 115(2) ?
C19 C22A H22A . . 122.7 ?
S4A C22A H22A . . 122.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.8280(17) ?
S1 C6 . 1.7524(18) ?
S2 C4 . 1.690(2) ?
S2 C5 . 1.7086(18) ?
O1 C11 . 1.225(2) ?
N1 C1 . 1.461(2) ?
N1 C11 . 1.369(2) ?
N1 C12 . 1.440(2) ?
N2 C6 . 1.339(2) ?
N2 C7 . 1.329(3) ?
C1 H1 . 0.9800 ?
C1 C2 . 1.506(2) ?
C2 C3 . 1.422(2) ?
C2 C5 . 1.359(2) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.361(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C10 . 1.395(2) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.376(3) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.369(3) ?
C9 H9 . 0.9300 ?
C9 C10 . 1.393(3) ?
C10 C11 . 1.490(2) ?
C12 C13 . 1.377(3) ?
C12 C17 . 1.389(2) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.385(3) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.370(3) ?
C15 H15 . 0.9300 ?
C15 C16 . 1.374(3) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.384(3) ?
C17 H17 . 0.9300 ?
S3 C18 . 1.8226(19) ?
S3 C23 . 1.7498(19) ?
S4B C21B . 1.655(9) ?
S4B C22B . 1.726(4) ?
O2 C28 . 1.224(2) ?
N3 C18 . 1.463(2) ?
N3 C28 . 1.369(2) ?
N3 C29 . 1.439(2) ?
N4 C23 . 1.337(2) ?
N4 C24 . 1.333(3) ?
C18 H18 . 0.9800 ?
C18 C19 . 1.509(2) ?
C19 C20B . 1.433(5) ?
C19 C22B . 1.350(5) ?
C19 C20A . 1.46(3) ?
C19 C22A . 1.31(3) ?
C20B H20B . 0.9300 ?
C20B C21B . 1.362(10) ?
C21B H21B . 0.9300 ?
C22B H22B . 0.9300 ?
C23 C27 . 1.398(2) ?
C24 H24 . 0.9300 ?
C24 C25 . 1.372(3) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.383(3) ?
C26 H26 . 0.9300 ?
C26 C27 . 1.387(2) ?
C27 C28 . 1.492(2) ?
C29 C30 . 1.377(2) ?
C29 C34 . 1.382(2) ?
C30 H30 . 0.9300 ?
C30 C31 . 1.384(3) ?
C31 H31 . 0.9300 ?
C31 C32 . 1.373(3) ?
C32 H32 . 0.9300 ?
C32 C33 . 1.365(3) ?
C33 H33 . 0.9300 ?
C33 C34 . 1.385(3) ?
C34 H34 . 0.9300 ?
C20A H20A . 0.9300 ?
C20A C21A . 1.32(3) ?
C21A H21A . 0.9300 ?
C21A S4A . 1.703(17) ?
S4A C22A . 1.69(3) ?
C22A H22A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 1_455 0.93 2.26 3.168(2) 164.5 yes
C18 H18 N2 3_666 0.98 2.53 3.494(2) 167.1 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 C1 C2 C3 . . . . -51.29(19) ?
S1 C1 C2 C5 . . . . 132.55(16) ?
S1 C6 C10 C9 . . . . -179.84(14) ?
S1 C6 C10 C11 . . . . -7.0(2) ?
N1 C1 C2 C3 . . . . -178.17(15) ?
N1 C1 C2 C5 . . . . 5.7(2) ?
N1 C12 C13 C14 . . . . -176.64(17) ?
N1 C12 C17 C16 . . . . 176.71(17) ?
N2 C6 C10 C9 . . . . -2.3(3) ?
N2 C6 C10 C11 . . . . 170.58(17) ?
N2 C7 C8 C9 . . . . -2.3(4) ?
C1 S1 C6 N2 . . . . 158.55(14) ?
C1 S1 C6 C10 . . . . -23.70(16) ?
C1 N1 C11 O1 . . . . -161.38(17) ?
C1 N1 C11 C10 . . . . 21.7(2) ?
C1 N1 C12 C13 . . . . 41.6(2) ?
C1 N1 C12 C17 . . . . -135.66(17) ?
C1 C2 C3 C4 . . . . -177.30(16) ?
C1 C2 C5 S2 . . . . 176.65(13) ?
C2 C3 C4 S2 . . . . 0.9(2) ?
C3 C2 C5 S2 . . . . 0.1(2) ?
C4 S2 C5 C2 . . . . 0.31(15) ?
C5 S2 C4 C3 . . . . -0.68(16) ?
C5 C2 C3 C4 . . . . -0.6(2) ?
C6 S1 C1 N1 . . . . 52.23(13) ?
C6 S1 C1 C2 . . . . -75.83(12) ?
C6 N2 C7 C8 . . . . 1.6(3) ?
C6 C10 C11 O1 . . . . -163.02(18) ?
C6 C10 C11 N1 . . . . 14.0(3) ?
C7 N2 C6 S1 . . . . 178.47(15) ?
C7 N2 C6 C10 . . . . 0.8(3) ?
C7 C8 C9 C10 . . . . 0.6(3) ?
C8 C9 C10 C6 . . . . 1.5(3) ?
C8 C9 C10 C11 . . . . -171.83(19) ?
C9 C10 C11 O1 . . . . 9.8(3) ?
C9 C10 C11 N1 . . . . -173.22(17) ?
C11 N1 C1 S1 . . . . -57.40(18) ?
C11 N1 C1 C2 . . . . 69.8(2) ?
C11 N1 C12 C13 . . . . -130.96(18) ?
C11 N1 C12 C17 . . . . 51.8(2) ?
C12 N1 C1 S1 . . . . 129.98(13) ?
C12 N1 C1 C2 . . . . -102.77(17) ?
C12 N1 C11 O1 . . . . 11.0(3) ?
C12 N1 C11 C10 . . . . -165.93(15) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C12 C17 C16 . . . . -0.6(3) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C17 . . . . -0.3(3) ?
C15 C16 C17 C12 . . . . 0.4(3) ?
C17 C12 C13 C14 . . . . 0.6(3) ?
S3 C18 C19 C20B . . . . 53.2(5) ?
S3 C18 C19 C22B . . . . -127.2(5) ?
S3 C18 C19 C20A . . . . -124(4) ?
S3 C18 C19 C22A . . . . 62(3) ?
S3 C23 C27 C26 . . . . -179.89(13) ?
S3 C23 C27 C28 . . . . 7.2(2) ?
N3 C18 C19 C20B . . . . 179.5(5) ?
N3 C18 C19 C22B . . . . -0.8(5) ?
N3 C18 C19 C20A . . . . 2(4) ?
N3 C18 C19 C22A . . . . -172(3) ?
N3 C29 C30 C31 . . . . -177.72(17) ?
N3 C29 C34 C33 . . . . 177.01(18) ?
N4 C23 C27 C26 . . . . 2.0(3) ?
N4 C23 C27 C28 . . . . -170.91(17) ?
N4 C24 C25 C26 . . . . 1.1(3) ?
C18 S3 C23 N4 . . . . -155.97(14) ?
C18 S3 C23 C27 . . . . 25.76(16) ?
C18 N3 C28 O2 . . . . 166.06(17) ?
C18 N3 C28 C27 . . . . -16.2(2) ?
C18 N3 C29 C30 . . . . 131.40(18) ?
C18 N3 C29 C34 . . . . -46.0(2) ?
C18 C19 C20B C21B . . . . 178.6(6) ?
C18 C19 C22B S4B . . . . -179.7(3) ?
C18 C19 C20A C21A . . . . -173(3) ?
C18 C19 C22A S4A . . . . -174(2) ?
C19 C20B C21B S4B . . . . 1.7(11) ?
C19 C20A C21A S4A . . . . -12(7) ?
C20B C19 C22B S4B . . . . 0.0(8) ?
C21B S4B C22B C19 . . . . 0.8(7) ?
C22B S4B C21B C20B . . . . -1.5(9) ?
C22B C19 C20B C21B . . . . -1.1(10) ?
C23 S3 C18 N3 . . . . -53.18(13) ?
C23 S3 C18 C19 . . . . 74.24(13) ?
C23 N4 C24 C25 . . . . 0.2(3) ?
C23 C27 C28 O2 . . . . 159.54(18) ?
C23 C27 C28 N3 . . . . -18.3(3) ?
C24 N4 C23 S3 . . . . 179.98(15) ?
C24 N4 C23 C27 . . . . -1.8(3) ?
C24 C25 C26 C27 . . . . -0.8(3) ?
C25 C26 C27 C23 . . . . -0.6(3) ?
C25 C26 C27 C28 . . . . 172.74(17) ?
C26 C27 C28 O2 . . . . -13.3(3) ?
C26 C27 C28 N3 . . . . 168.89(16) ?
C28 N3 C18 S3 . . . . 54.8(2) ?
C28 N3 C18 C19 . . . . -71.4(2) ?
C28 N3 C29 C30 . . . . -53.0(2) ?
C28 N3 C29 C34 . . . . 129.62(19) ?
C29 N3 C18 S3 . . . . -129.72(14) ?
C29 N3 C18 C19 . . . . 104.08(17) ?
C29 N3 C28 O2 . . . . -9.4(3) ?
C29 N3 C28 C27 . . . . 168.40(15) ?
C29 C30 C31 C32 . . . . 0.6(3) ?
C30 C29 C34 C33 . . . . -0.3(3) ?
C30 C31 C32 C33 . . . . 0.0(3) ?
C31 C32 C33 C34 . . . . -0.7(3) ?
C32 C33 C34 C29 . . . . 0.9(3) ?
C34 C29 C30 C31 . . . . -0.4(3) ?
C20A C19 C22A S4A . . . . 10(6) ?
C20A C21A S4A C22A . . . . 15(5) ?
C21A S4A C22A C19 . . . . -15(5) ?
C22A C19 C20A C21A . . . . 2(7) ?