#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:35:54 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244545 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/90/7239099.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_7239099
loop_
_publ_author_name
'Blumberg, Laura C.'
'Zeidan, Tarek A.'
'Maddaford, Adrian'
'Warren, Nicole C.'
'Hutchison, Panee'
_publ_section_title
;
 Novel N-5-(acyloxyalkoxy)carbonyl prodrugs of olanzapine with
 physicochemical properties for extended-release
;
_journal_issue                   37
_journal_name_full               'RSC Advances'
_journal_page_first              16270
_journal_paper_doi               10.1039/c3ra41967c
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C35 H52 N4 O4 S'
_chemical_formula_sum            'C35 H52 N4 O4 S'
_chemical_formula_weight         624.87
_chemical_melting_point          406
_chemical_name_systematic
;
(hexanoyloxy) methyl
2-methyl-4-(4-methylpiperazin-1-yl)-5H-benzo[b]thieno[2,3-e][1,4]diazepine-5-\
carboxylate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-02-12 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.753(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4300(15)
_cell_length_b                   14.9488(15)
_cell_length_c                   16.2240(14)
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.84
_cell_measurement_theta_min      3.07
_cell_volume                     3495.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20769
_diffrn_reflns_theta_full        69.56
_diffrn_reflns_theta_max         69.56
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_T_max  0.8926
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.3700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                4951
_reflns_number_total             6061
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL 3bc(C6) in P2(1)/c
CELL 1.54178 14.4300 14.9488 16.2240 90.000 92.753 90.000
ZERR 4.00 0.0015 0.0015 0.0014 0.000 0.007 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O S
UNIT 140 208 16 16 4

OMIT 10 1 14

L.S. 9
ACTA
BOND $H
FMAP 2
PLAN 6
SIZE 0.101 0.161 0.318
HTAB
CONF
TEMP -100.000
WGHT 0.052000 0.370000
FVAR 0.07441
C1 1 0.608364 0.705232 1.299356 11.00000 0.03316 0.02012 =
0.02952 0.00076 0.00197 -0.00072
C2 1 0.669990 0.680412 1.363462 11.00000 0.04212 0.02983 =
0.02845 0.00226 -0.00051 0.00063
AFIX 43
H2A 2 0.663455 0.704007 1.417242 11.00000 -1.20000
AFIX 0
C3 1 0.741035 0.621188 1.348914 11.00000 0.03787 0.03674 =
0.03819 0.00772 -0.00481 0.00264
AFIX 43
H3A 2 0.783825 0.604276 1.392465 11.00000 -1.20000
AFIX 0
C4 1 0.749324 0.586613 1.270059 11.00000 0.03211 0.03079 =
0.04500 -0.00096 0.00018 0.00351
AFIX 43
H4A 2 0.796435 0.544044 1.260302 11.00000 -1.20000
AFIX 0
C5 1 0.689835 0.613574 1.206075 11.00000 0.03671 0.03177 =
0.03605 -0.00592 0.00143 0.00144
AFIX 43
H5A 2 0.697117 0.589669 1.152518 11.00000 -1.20000
AFIX 0
C6 1 0.618268 0.675853 1.218012 11.00000 0.03307 0.02395 =
0.02948 -0.00231 -0.00101 -0.00250
C7 1 0.518495 0.776746 1.144426 11.00000 0.03161 0.02735 =
0.02226 -0.00229 0.00074 -0.00251
C8 1 0.436919 0.910770 1.075181 11.00000 0.03556 0.02845 =
0.02398 0.00135 0.00260 -0.00047
C9 1 0.467683 0.929462 1.152823 11.00000 0.03983 0.02227 =
0.02448 -0.00036 0.00217 -0.00016
AFIX 43
H9A 2 0.461816 0.987032 1.176818 11.00000 -1.20000
AFIX 0
C10 1 0.510659 0.854458 1.197108 11.00000 0.03316 0.02230 =
0.02293 -0.00041 0.00170 -0.00120
C11 1 0.532222 0.848211 1.281516 11.00000 0.03050 0.01953 =
0.02430 0.00015 0.00377 0.00082
C12 1 0.572653 1.005468 1.309664 11.00000 0.04709 0.02106 =
0.02570 0.00075 -0.00050 -0.00186
AFIX 23
H12A 2 0.515640 1.041763 1.313531 11.00000 -1.20000
H12B 2 0.590074 1.005618 1.251383 11.00000 -1.20000
AFIX 0
C13 1 0.650179 1.046970 1.363198 11.00000 0.04534 0.02655 =
0.03128 -0.00248 0.00399 -0.00533
AFIX 23
H13A 2 0.709408 1.016835 1.352170 11.00000 -1.20000
H13B 2 0.656325 1.110919 1.348568 11.00000 -1.20000
AFIX 0
C14 1 0.623820 0.945618 1.472612 11.00000 0.04401 0.02984 =
0.02441 -0.00116 -0.00319 0.00155
AFIX 23
H14A 2 0.614358 0.940258 1.532444 11.00000 -1.20000
H14B 2 0.681581 0.913411 1.460599 11.00000 -1.20000
AFIX 0
C15 1 0.543126 0.903964 1.424571 11.00000 0.04280 0.02687 =
0.02126 -0.00114 0.00511 -0.00280
AFIX 23
H15A 2 0.539036 0.839726 1.438785 11.00000 -1.20000
H15B 2 0.484817 0.933260 1.439729 11.00000 -1.20000
AFIX 0
C16 1 0.705597 1.082929 1.501120 11.00000 0.04915 0.04406 =
0.04259 -0.01066 -0.00438 -0.00789
AFIX 33
H16A 2 0.692440 1.076807 1.559552 11.00000 -1.50000
H16B 2 0.708027 1.146502 1.486636 11.00000 -1.50000
H16C 2 0.765400 1.054874 1.491114 11.00000 -1.50000
AFIX 0
C17 1 0.384465 0.970561 1.015322 11.00000 0.04380 0.03355 =
0.02810 0.00296 -0.00093 0.00298
AFIX 33
H17A 2 0.375959 1.029351 1.040597 11.00000 -1.50000
H17B 2 0.323702 0.944130 1.000831 11.00000 -1.50000
H17C 2 0.419423 0.977316 0.965382 11.00000 -1.50000
AFIX 0
C18 1 0.446595 0.719909 1.327610 11.00000 0.03733 0.02551 =
0.01666 -0.00265 0.00079 -0.00290
C19 1 0.287249 0.752234 1.328768 11.00000 0.03425 0.04474 =
0.03026 -0.00360 0.00273 -0.00728
AFIX 23
H19A 2 0.246210 0.793439 1.357884 11.00000 -1.20000
H19B 2 0.283932 0.692460 1.354731 11.00000 -1.20000
AFIX 0
C20 1 0.205627 0.815202 1.211667 11.00000 0.03490 0.03772 =
0.03725 -0.00274 0.00327 -0.00626
C21 1 0.198308 0.806270 1.119627 11.00000 0.03854 0.05068 =
0.03626 -0.00334 0.00272 0.00016
AFIX 23
H21A 2 0.181632 0.743579 1.105974 11.00000 -1.20000
H21B 2 0.260341 0.817627 1.098258 11.00000 -1.20000
AFIX 0
C22 1 0.129105 0.867164 1.074171 11.00000 0.04128 0.04530 =
0.03870 -0.00255 0.00177 -0.00251
AFIX 23
H22A 2 0.144217 0.930442 1.086809 11.00000 -1.20000
H22B 2 0.065808 0.854839 1.092261 11.00000 -1.20000
AFIX 0
C23 1 0.132937 0.850750 0.981571 11.00000 0.03875 0.05178 =
0.03785 -0.00266 -0.00088 -0.00249
AFIX 23
H23A 2 0.196049 0.866475 0.965034 11.00000 -1.20000
H23B 2 0.124652 0.785811 0.971774 11.00000 -1.20000
AFIX 0
C24 1 0.063900 0.899830 0.924581 11.00000 0.04227 0.05176 =
0.04292 -0.00270 -0.00052 0.00059
AFIX 23
H24A 2 0.070620 0.965150 0.932964 11.00000 -1.20000
H24B 2 -0.000034 0.882709 0.937617 11.00000 -1.20000
AFIX 0
C25 1 0.080661 0.876551 0.834730 11.00000 0.03756 0.05007 =
0.04222 -0.00125 -0.00104 0.00199
AFIX 23
H25A 2 0.141471 0.901721 0.820985 11.00000 -1.20000
H25B 2 0.085330 0.810673 0.830256 11.00000 -1.20000
AFIX 0
C26 1 0.008738 0.908539 0.770458 11.00000 0.04082 0.05203 =
0.04328 -0.00035 -0.00194 0.00540
AFIX 23
H26A 2 0.007382 0.974752 0.770295 11.00000 -1.20000
H26B 2 -0.053255 0.886965 0.784990 11.00000 -1.20000
AFIX 0
C27 1 0.029540 0.875053 0.684558 11.00000 0.03857 0.05026 =
0.04337 0.00083 -0.00163 0.00408
AFIX 23
H27A 2 0.090817 0.898620 0.670188 11.00000 -1.20000
H27B 2 0.034348 0.809015 0.686445 11.00000 -1.20000
AFIX 0
C28 1 -0.041362 0.900535 0.616102 11.00000 0.04291 0.05202 =
0.04220 -0.00146 -0.00219 0.00783
AFIX 23
H28A 2 -0.043426 0.966523 0.611184 11.00000 -1.20000
H28B 2 -0.103471 0.880000 0.631365 11.00000 -1.20000
AFIX 0
C29 1 -0.020047 0.860688 0.532740 11.00000 0.04251 0.05117 =
0.04323 -0.00017 -0.00106 0.00633
AFIX 23
H29A 2 0.041538 0.882275 0.517082 11.00000 -1.20000
H29B 2 -0.016497 0.794795 0.538135 11.00000 -1.20000
AFIX 0
C30 1 -0.091255 0.883875 0.464272 11.00000 0.04545 0.05279 =
0.04042 -0.00081 -0.00006 0.00775
AFIX 23
H30A 2 -0.093056 0.949753 0.458159 11.00000 -1.20000
H30B 2 -0.153031 0.864521 0.481470 11.00000 -1.20000
AFIX 0
C31 1 -0.075028 0.842987 0.380301 11.00000 0.04742 0.04998 =
0.04387 -0.00386 -0.00089 0.00797
AFIX 23
H31A 2 -0.012897 0.860856 0.362813 11.00000 -1.20000
H31B 2 -0.075998 0.776965 0.384968 11.00000 -1.20000
AFIX 0
C32 1 -0.147833 0.872256 0.315165 11.00000 0.04559 0.04464 =
0.04175 -0.00187 0.00052 0.00245
AFIX 23
H32A 2 -0.209638 0.856046 0.334562 11.00000 -1.20000
H32B 2 -0.145651 0.938284 0.310963 11.00000 -1.20000
AFIX 0
C33 1 -0.139397 0.833822 0.229799 11.00000 0.05413 0.04986 =
0.04173 -0.00160 -0.00062 0.00289
AFIX 23
H33A 2 -0.143805 0.767821 0.232770 11.00000 -1.20000
H33B 2 -0.077583 0.849039 0.209829 11.00000 -1.20000
AFIX 0
C34 1 -0.213698 0.868412 0.168485 11.00000 0.06047 0.05683 =
0.04421 0.00142 -0.00317 -0.00130
AFIX 23
H34A 2 -0.275268 0.855412 0.190105 11.00000 -1.20000
H34B 2 -0.207619 0.934222 0.164569 11.00000 -1.20000
AFIX 0
C35 1 -0.210397 0.829393 0.082985 11.00000 0.10013 0.09068 =
0.04464 -0.00159 -0.01169 0.00831
AFIX 33
H35A 2 -0.260093 0.855520 0.047396 11.00000 -1.50000
H35B 2 -0.218725 0.764413 0.085663 11.00000 -1.50000
H35C 2 -0.150228 0.842883 0.060320 11.00000 -1.50000
AFIX 0
N1 3 0.529783 0.759917 1.315505 11.00000 0.03432 0.01906 =
0.02411 0.00047 0.00203 -0.00018
N2 3 0.563019 0.700484 1.149606 11.00000 0.03559 0.02764 =
0.02846 -0.00608 -0.00066 0.00273
N3 3 0.554055 0.913537 1.335327 11.00000 0.03808 0.02166 =
0.02021 -0.00011 0.00154 -0.00136
N4 3 0.632900 1.039383 1.450844 11.00000 0.03998 0.02824 =
0.02667 -0.00453 -0.00094 -0.00243
O1 4 0.433808 0.640837 1.335253 11.00000 0.04773 0.02363 =
0.03143 -0.00057 0.00376 -0.00802
O2 4 0.380024 0.784378 1.334095 11.00000 0.03160 0.02981 =
0.03071 -0.00410 0.00324 -0.00322
O3 4 0.258542 0.746913 1.243910 11.00000 0.04102 0.04542 =
0.03246 -0.00927 -0.00273 0.00134
O4 4 0.171112 0.871629 1.252537 11.00000 0.07535 0.04389 =
0.04311 -0.00584 0.00506 0.01140
S1 5 0.463200 0.800627 1.047047 11.00000 0.04182 0.03157 =
0.02345 -0.00505 -0.00306 0.00387
HKLF 4

REM 3bc(C6) in P2(1)/c
REM R1 = 0.0370 for 4951 Fo > 4sig(Fo) and 0.0472 for all 6061 data
REM 397 parameters refined using 0 restraints

END

WGHT 0.0519 0.3397
REM Highest difference peak 0.247, deepest hole -0.225, 1-sigma level 0.040
Q1 1 0.3171 0.9719 1.0292 11.00000 0.05 0.25
Q2 1 0.4187 1.0421 1.0253 11.00000 0.05 0.24
Q3 1 0.3846 0.9513 0.9566 11.00000 0.05 0.20
Q4 1 0.6196 0.7042 1.2563 11.00000 0.05 0.19
Q5 1 0.5184 0.8165 1.1714 11.00000 0.05 0.18
Q6 1 0.4558 0.8676 1.0645 11.00000 0.05 0.16

;
_cod_data_source_file            c3ra41967c.txt
_cod_data_source_block           3bc(C6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7239099
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.60836(10) 0.70523(10) 1.29936(9) 0.0276(3) Uani 1 1 d .
C2 C 0.66999(11) 0.68041(11) 1.36346(10) 0.0335(3) Uani 1 1 d .
H2A H 0.6635 0.7040 1.4172 0.040 Uiso 1 1 calc R
C3 C 0.74104(11) 0.62119(12) 1.34891(10) 0.0378(4) Uani 1 1 d .
H3A H 0.7838 0.6043 1.3925 0.045 Uiso 1 1 calc R
C4 C 0.74932(11) 0.58661(11) 1.27006(10) 0.0360(4) Uani 1 1 d .
H4A H 0.7964 0.5440 1.2603 0.043 Uiso 1 1 calc R
C5 C 0.68983(11) 0.61357(11) 1.20607(10) 0.0349(3) Uani 1 1 d .
H5A H 0.6971 0.5897 1.1525 0.042 Uiso 1 1 calc R
C6 C 0.61827(10) 0.67585(10) 1.21801(9) 0.0289(3) Uani 1 1 d .
C7 C 0.51849(10) 0.77675(10) 1.14443(9) 0.0271(3) Uani 1 1 d .
C8 C 0.43692(10) 0.91077(10) 1.07518(9) 0.0293(3) Uani 1 1 d .
C9 C 0.46768(10) 0.92946(10) 1.15282(9) 0.0288(3) Uani 1 1 d .
H9A H 0.4618 0.9870 1.1768 0.035 Uiso 1 1 calc R
C10 C 0.51066(10) 0.85446(10) 1.19711(9) 0.0261(3) Uani 1 1 d .
C11 C 0.53222(10) 0.84821(9) 1.28152(9) 0.0247(3) Uani 1 1 d .
C12 C 0.57265(11) 1.00547(10) 1.30966(9) 0.0314(3) Uani 1 1 d .
H12A H 0.5156 1.0418 1.3135 0.038 Uiso 1 1 calc R
H12B H 0.5901 1.0056 1.2514 0.038 Uiso 1 1 calc R
C13 C 0.65018(11) 1.04697(11) 1.36320(9) 0.0343(3) Uani 1 1 d .
H13A H 0.7094 1.0168 1.3522 0.041 Uiso 1 1 calc R
H13B H 0.6563 1.1109 1.3486 0.041 Uiso 1 1 calc R
C14 C 0.62382(11) 0.94562(10) 1.47261(9) 0.0329(3) Uani 1 1 d .
H14A H 0.6144 0.9403 1.5324 0.039 Uiso 1 1 calc R
H14B H 0.6816 0.9134 1.4606 0.039 Uiso 1 1 calc R
C15 C 0.54313(11) 0.90396(10) 1.42457(8) 0.0302(3) Uani 1 1 d .
H15A H 0.5390 0.8397 1.4388 0.036 Uiso 1 1 calc R
H15B H 0.4848 0.9333 1.4397 0.036 Uiso 1 1 calc R
C16 C 0.70560(13) 1.08293(13) 1.50112(11) 0.0455(4) Uani 1 1 d .
H16A H 0.6924 1.0768 1.5596 0.068 Uiso 1 1 calc R
H16B H 0.7080 1.1465 1.4866 0.068 Uiso 1 1 calc R
H16C H 0.7654 1.0549 1.4911 0.068 Uiso 1 1 calc R
C17 C 0.38447(12) 0.97056(11) 1.01532(9) 0.0352(3) Uani 1 1 d .
H17A H 0.3760 1.0294 1.0406 0.053 Uiso 1 1 calc R
H17B H 0.3237 0.9441 1.0008 0.053 Uiso 1 1 calc R
H17C H 0.4194 0.9773 0.9654 0.053 Uiso 1 1 calc R
C18 C 0.44660(10) 0.71991(10) 1.32761(8) 0.0265(3) Uani 1 1 d .
C19 C 0.28725(11) 0.75223(12) 1.32877(10) 0.0364(4) Uani 1 1 d .
H19A H 0.2462 0.7934 1.3579 0.044 Uiso 1 1 calc R
H19B H 0.2839 0.6925 1.3547 0.044 Uiso 1 1 calc R
C20 C 0.20563(11) 0.81520(12) 1.21167(10) 0.0366(4) Uani 1 1 d .
C21 C 0.19831(12) 0.80627(13) 1.11963(10) 0.0418(4) Uani 1 1 d .
H21A H 0.1816 0.7436 1.1060 0.050 Uiso 1 1 calc R
H21B H 0.2603 0.8176 1.0983 0.050 Uiso 1 1 calc R
C22 C 0.12911(12) 0.86716(13) 1.07417(10) 0.0418(4) Uani 1 1 d .
H22A H 0.1442 0.9304 1.0868 0.050 Uiso 1 1 calc R
H22B H 0.0658 0.8548 1.0923 0.050 Uiso 1 1 calc R
C23 C 0.13294(12) 0.85075(13) 0.98157(10) 0.0429(4) Uani 1 1 d .
H23A H 0.1960 0.8665 0.9650 0.051 Uiso 1 1 calc R
H23B H 0.1247 0.7858 0.9718 0.051 Uiso 1 1 calc R
C24 C 0.06390(13) 0.89983(14) 0.92458(11) 0.0457(4) Uani 1 1 d .
H24A H 0.0706 0.9652 0.9330 0.055 Uiso 1 1 calc R
H24B H 0.0000 0.8827 0.9376 0.055 Uiso 1 1 calc R
C25 C 0.08066(12) 0.87655(13) 0.83473(11) 0.0434(4) Uani 1 1 d .
H25A H 0.1415 0.9017 0.8210 0.052 Uiso 1 1 calc R
H25B H 0.0853 0.8107 0.8303 0.052 Uiso 1 1 calc R
C26 C 0.00874(13) 0.90854(14) 0.77046(11) 0.0455(4) Uani 1 1 d .
H26A H 0.0074 0.9748 0.7703 0.055 Uiso 1 1 calc R
H26B H -0.0533 0.8870 0.7850 0.055 Uiso 1 1 calc R
C27 C 0.02954(12) 0.87505(13) 0.68456(11) 0.0442(4) Uani 1 1 d .
H27A H 0.0908 0.8986 0.6702 0.053 Uiso 1 1 calc R
H27B H 0.0343 0.8090 0.6864 0.053 Uiso 1 1 calc R
C28 C -0.04136(13) 0.90054(14) 0.61610(11) 0.0458(4) Uani 1 1 d .
H28A H -0.0434 0.9665 0.6112 0.055 Uiso 1 1 calc R
H28B H -0.1035 0.8800 0.6314 0.055 Uiso 1 1 calc R
C29 C -0.02005(13) 0.86069(14) 0.53274(11) 0.0457(4) Uani 1 1 d .
H29A H 0.0415 0.8823 0.5171 0.055 Uiso 1 1 calc R
H29B H -0.0165 0.7948 0.5381 0.055 Uiso 1 1 calc R
C30 C -0.09125(13) 0.88387(14) 0.46427(11) 0.0463(4) Uani 1 1 d .
H30A H -0.0931 0.9498 0.4582 0.056 Uiso 1 1 calc R
H30B H -0.1530 0.8645 0.4815 0.056 Uiso 1 1 calc R
C31 C -0.07503(13) 0.84299(14) 0.38030(11) 0.0472(4) Uani 1 1 d .
H31A H -0.0129 0.8609 0.3628 0.057 Uiso 1 1 calc R
H31B H -0.0760 0.7770 0.3850 0.057 Uiso 1 1 calc R
C32 C -0.14783(13) 0.87226(13) 0.31517(11) 0.0440(4) Uani 1 1 d .
H32A H -0.2096 0.8560 0.3346 0.053 Uiso 1 1 calc R
H32B H -0.1457 0.9383 0.3110 0.053 Uiso 1 1 calc R
C33 C -0.13940(14) 0.83382(14) 0.22980(11) 0.0487(4) Uani 1 1 d .
H33A H -0.1438 0.7678 0.2328 0.058 Uiso 1 1 calc R
H33B H -0.0776 0.8490 0.2098 0.058 Uiso 1 1 calc R
C34 C -0.21370(15) 0.86841(15) 0.16848(12) 0.0540(5) Uani 1 1 d .
H34A H -0.2753 0.8554 0.1901 0.065 Uiso 1 1 calc R
H34B H -0.2076 0.9342 0.1646 0.065 Uiso 1 1 calc R
C35 C -0.2104(2) 0.8294(2) 0.08298(14) 0.0790(8) Uani 1 1 d .
H35A H -0.2601 0.8555 0.0474 0.118 Uiso 1 1 calc R
H35B H -0.2187 0.7644 0.0857 0.118 Uiso 1 1 calc R
H35C H -0.1502 0.8429 0.0603 0.118 Uiso 1 1 calc R
N1 N 0.52978(8) 0.75992(8) 1.31550(7) 0.0258(3) Uani 1 1 d .
N2 N 0.56302(9) 0.70048(9) 1.14961(8) 0.0306(3) Uani 1 1 d .
N3 N 0.55405(9) 0.91354(8) 1.33533(7) 0.0266(3) Uani 1 1 d .
N4 N 0.63290(9) 1.03938(9) 1.45084(8) 0.0317(3) Uani 1 1 d .
O1 O 0.43381(8) 0.64084(7) 1.33525(6) 0.0342(3) Uani 1 1 d .
O2 O 0.38002(7) 0.78438(7) 1.33410(6) 0.0307(2) Uani 1 1 d .
O3 O 0.25854(8) 0.74691(8) 1.24391(7) 0.0398(3) Uani 1 1 d .
O4 O 0.17111(11) 0.87163(9) 1.25254(8) 0.0540(4) Uani 1 1 d .
S1 S 0.46320(3) 0.80063(3) 1.04705(2) 0.03243(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0332(7) 0.0201(7) 0.0295(7) 0.0008(6) 0.0020(6) -0.0007(5)
C2 0.0421(9) 0.0298(9) 0.0285(8) 0.0023(6) -0.0005(7) 0.0006(6)
C3 0.0379(9) 0.0367(10) 0.0382(9) 0.0077(7) -0.0048(7) 0.0026(6)
C4 0.0321(8) 0.0308(9) 0.0450(9) -0.0010(7) 0.0002(7) 0.0035(6)
C5 0.0367(8) 0.0318(9) 0.0360(8) -0.0059(7) 0.0014(7) 0.0014(6)
C6 0.0331(8) 0.0240(8) 0.0295(8) -0.0023(6) -0.0010(6) -0.0025(5)
C7 0.0316(7) 0.0273(8) 0.0223(7) -0.0023(6) 0.0007(6) -0.0025(5)
C8 0.0356(8) 0.0285(8) 0.0240(7) 0.0014(6) 0.0026(6) -0.0005(6)
C9 0.0398(8) 0.0223(8) 0.0245(7) -0.0004(6) 0.0022(6) -0.0002(6)
C10 0.0332(7) 0.0223(8) 0.0229(7) -0.0004(6) 0.0017(6) -0.0012(5)
C11 0.0305(7) 0.0195(7) 0.0243(7) 0.0001(5) 0.0038(6) 0.0008(5)
C12 0.0471(9) 0.0211(8) 0.0257(7) 0.0007(6) -0.0005(6) -0.0019(6)
C13 0.0453(9) 0.0266(8) 0.0313(8) -0.0025(6) 0.0040(7) -0.0053(6)
C14 0.0440(9) 0.0298(9) 0.0244(7) -0.0012(6) -0.0032(6) 0.0016(6)
C15 0.0428(8) 0.0269(8) 0.0213(7) -0.0011(6) 0.0051(6) -0.0028(6)
C16 0.0491(10) 0.0441(11) 0.0426(9) -0.0107(8) -0.0044(8) -0.0079(8)
C17 0.0438(9) 0.0335(9) 0.0281(7) 0.0030(7) -0.0009(7) 0.0030(6)
C18 0.0373(8) 0.0255(8) 0.0167(6) -0.0027(5) 0.0008(6) -0.0029(6)
C19 0.0342(8) 0.0447(10) 0.0303(8) -0.0036(7) 0.0027(7) -0.0073(6)
C20 0.0349(8) 0.0377(10) 0.0373(9) -0.0027(7) 0.0033(7) -0.0063(6)
C21 0.0385(9) 0.0507(11) 0.0363(9) -0.0033(8) 0.0027(7) 0.0002(7)
C22 0.0413(9) 0.0453(11) 0.0387(9) -0.0025(8) 0.0018(7) -0.0025(7)
C23 0.0387(9) 0.0518(11) 0.0378(9) -0.0027(8) -0.0009(7) -0.0025(7)
C24 0.0423(9) 0.0518(12) 0.0429(10) -0.0027(8) -0.0005(8) 0.0006(7)
C25 0.0376(9) 0.0501(11) 0.0422(9) -0.0013(8) -0.0010(7) 0.0020(7)
C26 0.0408(9) 0.0520(12) 0.0433(10) -0.0004(8) -0.0019(8) 0.0054(7)
C27 0.0386(9) 0.0503(11) 0.0434(10) 0.0008(8) -0.0016(8) 0.0041(7)
C28 0.0429(10) 0.0520(12) 0.0422(10) -0.0015(8) -0.0022(8) 0.0078(7)
C29 0.0425(10) 0.0512(12) 0.0432(10) -0.0002(8) -0.0011(8) 0.0063(8)
C30 0.0454(10) 0.0528(12) 0.0404(9) -0.0008(8) -0.0001(8) 0.0077(8)
C31 0.0474(10) 0.0500(12) 0.0439(10) -0.0039(8) -0.0009(8) 0.0080(8)
C32 0.0456(10) 0.0446(11) 0.0417(9) -0.0019(8) 0.0005(8) 0.0025(7)
C33 0.0541(11) 0.0499(12) 0.0417(10) -0.0016(8) -0.0006(9) 0.0029(8)
C34 0.0605(12) 0.0568(13) 0.0442(10) 0.0014(9) -0.0032(9) -0.0013(9)
C35 0.100(2) 0.091(2) 0.0446(12) -0.0016(13) -0.0117(13) 0.0083(15)
N1 0.0343(6) 0.0191(6) 0.0241(6) 0.0005(5) 0.0020(5) -0.0002(5)
N2 0.0356(7) 0.0276(7) 0.0285(6) -0.0061(5) -0.0007(5) 0.0027(5)
N3 0.0381(7) 0.0217(7) 0.0202(6) -0.0001(5) 0.0015(5) -0.0014(5)
N4 0.0400(7) 0.0282(7) 0.0267(6) -0.0045(5) -0.0009(5) -0.0024(5)
O1 0.0477(6) 0.0236(6) 0.0314(5) -0.0006(4) 0.0038(5) -0.0080(4)
O2 0.0316(5) 0.0298(6) 0.0307(5) -0.0041(4) 0.0032(4) -0.0032(4)
O3 0.0410(6) 0.0454(7) 0.0325(6) -0.0093(5) -0.0027(5) 0.0013(5)
O4 0.0754(10) 0.0439(8) 0.0431(7) -0.0058(6) 0.0051(7) 0.0114(7)
S1 0.0418(2) 0.0316(2) 0.02345(18) -0.00505(15) -0.00306(15) 0.00387(15)
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 122.05(14)
C2 C1 N1 120.04(13)
C6 C1 N1 117.87(13)
C3 C2 C1 119.82(15)
C3 C2 H2A 120.1
C1 C2 H2A 120.1
C2 C3 C4 119.48(15)
C2 C3 H3A 120.3
C4 C3 H3A 120.3
C5 C4 C3 120.50(15)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 121.62(15)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
N2 C6 C1 126.10(14)
N2 C6 C5 117.55(14)
C1 C6 C5 116.33(14)
N2 C7 C10 135.38(14)
N2 C7 S1 115.55(11)
C10 C7 S1 108.64(11)
C9 C8 C17 128.10(14)
C9 C8 S1 111.89(12)
C17 C8 S1 119.99(11)
C8 C9 C10 114.60(13)
C8 C9 H9A 122.7
C10 C9 H9A 122.7
C11 C10 C7 120.39(13)
C11 C10 C9 127.39(13)
C7 C10 C9 111.71(12)
N3 C11 C10 128.86(13)
N3 C11 N1 115.54(12)
C10 C11 N1 115.60(13)
N3 C12 C13 111.19(12)
N3 C12 H12A 109.4
C13 C12 H12A 109.4
N3 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
N4 C13 C12 111.74(13)
N4 C13 H13A 109.3
C12 C13 H13A 109.3
N4 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 107.9
N4 C14 C15 110.48(13)
N4 C14 H14A 109.6
C15 C14 H14A 109.6
N4 C14 H14B 109.6
C15 C14 H14B 109.6
H14A C14 H14B 108.1
N3 C15 C14 110.65(12)
N3 C15 H15A 109.5
C14 C15 H15A 109.5
N3 C15 H15B 109.5
C14 C15 H15B 109.5
H15A C15 H15B 108.1
N4 C16 H16A 109.5
N4 C16 H16B 109.5
H16A C16 H16B 109.5
N4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 C17 H17A 109.5
C8 C17 H17B 109.5
H17A C17 H17B 109.5
C8 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O1 C18 N1 125.86(14)
O1 C18 O2 124.89(14)
N1 C18 O2 109.16(12)
O2 C19 O3 107.93(12)
O2 C19 H19A 110.1
O3 C19 H19A 110.1
O2 C19 H19B 110.1
O3 C19 H19B 110.1
H19A C19 H19B 108.4
O4 C20 O3 123.74(16)
O4 C20 C21 127.17(17)
O3 C20 C21 109.09(14)
C20 C21 C22 116.40(15)
C20 C21 H21A 108.2
C22 C21 H21A 108.2
C20 C21 H21B 108.2
C22 C21 H21B 108.2
H21A C21 H21B 107.3
C21 C22 C23 109.16(15)
C21 C22 H22A 109.8
C23 C22 H22A 109.8
C21 C22 H22B 109.8
C23 C22 H22B 109.8
H22A C22 H22B 108.3
C24 C23 C22 117.97(15)
C24 C23 H23A 107.8
C22 C23 H23A 107.8
C24 C23 H23B 107.8
C22 C23 H23B 107.8
H23A C23 H23B 107.2
C23 C24 C25 110.00(15)
C23 C24 H24A 109.7
C25 C24 H24A 109.7
C23 C24 H24B 109.7
C25 C24 H24B 109.7
H24A C24 H24B 108.2
C26 C25 C24 116.77(15)
C26 C25 H25A 108.1
C24 C25 H25A 108.1
C26 C25 H25B 108.1
C24 C25 H25B 108.1
H25A C25 H25B 107.3
C25 C26 C27 111.57(15)
C25 C26 H26A 109.3
C27 C26 H26A 109.3
C25 C26 H26B 109.3
C27 C26 H26B 109.3
H26A C26 H26B 108.0
C28 C27 C26 115.47(15)
C28 C27 H27A 108.4
C26 C27 H27A 108.4
C28 C27 H27B 108.4
C26 C27 H27B 108.4
H27A C27 H27B 107.5
C27 C28 C29 113.13(15)
C27 C28 H28A 109.0
C29 C28 H28A 109.0
C27 C28 H28B 109.0
C29 C28 H28B 109.0
H28A C28 H28B 107.8
C30 C29 C28 113.73(15)
C30 C29 H29A 108.8
C28 C29 H29A 108.8
C30 C29 H29B 108.8
C28 C29 H29B 108.8
H29A C29 H29B 107.7
C29 C30 C31 115.85(16)
C29 C30 H30A 108.3
C31 C30 H30A 108.3
C29 C30 H30B 108.3
C31 C30 H30B 108.3
H30A C30 H30B 107.4
C32 C31 C30 112.11(15)
C32 C31 H31A 109.2
C30 C31 H31A 109.2
C32 C31 H31B 109.2
C30 C31 H31B 109.2
H31A C31 H31B 107.9
C33 C32 C31 116.44(16)
C33 C32 H32A 108.2
C31 C32 H32A 108.2
C33 C32 H32B 108.2
C31 C32 H32B 108.2
H32A C32 H32B 107.3
C32 C33 C34 112.71(16)
C32 C33 H33A 109.1
C34 C33 H33A 109.1
C32 C33 H33B 109.1
C34 C33 H33B 109.1
H33A C33 H33B 107.8
C35 C34 C33 114.75(19)
C35 C34 H34A 108.6
C33 C34 H34A 108.6
C35 C34 H34B 108.6
C33 C34 H34B 108.6
H34A C34 H34B 107.6
C34 C35 H35A 109.5
C34 C35 H35B 109.5
H35A C35 H35B 109.5
C34 C35 H35C 109.5
H35A C35 H35C 109.5
H35B C35 H35C 109.5
C18 N1 C11 119.86(12)
C18 N1 C1 119.09(12)
C11 N1 C1 114.93(11)
C7 N2 C6 123.01(13)
C11 N3 C12 122.70(12)
C11 N3 C15 122.58(12)
C12 N3 C15 113.64(12)
C16 N4 C14 111.54(13)
C16 N4 C13 111.09(13)
C14 N4 C13 109.47(12)
C18 O2 C19 114.83(12)
C20 O3 C19 117.49(13)
C8 S1 C7 92.91(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.386(2)
C1 C6 1.405(2)
C1 N1 1.4322(18)
C2 C3 1.383(2)
C2 H2A 0.9500
C3 C4 1.390(2)
C3 H3A 0.9500
C4 C5 1.375(2)
C4 H4A 0.9500
C5 C6 1.411(2)
C5 H5A 0.9500
C6 N2 1.385(2)
C7 N2 1.309(2)
C7 C10 1.450(2)
C7 S1 1.7717(15)
C8 C9 1.345(2)
C8 C17 1.498(2)
C8 S1 1.7549(16)
C9 C10 1.454(2)
C9 H9A 0.9500
C10 C11 1.393(2)
C11 N3 1.3374(19)
C11 N1 1.4315(18)
C12 N3 1.4645(19)
C12 C13 1.516(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 N4 1.4598(19)
C13 H13A 0.9900
C13 H13B 0.9900
C14 N4 1.453(2)
C14 C15 1.505(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 N3 1.4709(17)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N4 1.452(2)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 O1 1.2037(19)
C18 N1 1.3638(19)
C18 O2 1.3683(18)
C19 O2 1.4211(18)
C19 O3 1.4208(19)
C19 H19A 0.9900
C19 H19B 0.9900
C20 O4 1.196(2)
C20 O3 1.364(2)
C20 C21 1.498(2)
C21 C22 1.516(2)
C21 H21A 0.9900
C21 H21B 0.9900
C22 C23 1.526(2)
C22 H22A 0.9900
C22 H22B 0.9900
C23 C24 1.516(3)
C23 H23A 0.9900
C23 H23B 0.9900
C24 C25 1.529(2)
C24 H24A 0.9900
C24 H24B 0.9900
C25 C26 1.513(2)
C25 H25A 0.9900
C25 H25B 0.9900
C26 C27 1.524(2)
C26 H26A 0.9900
C26 H26B 0.9900
C27 C28 1.522(2)
C27 H27A 0.9900
C27 H27B 0.9900
C28 C29 1.523(3)
C28 H28A 0.9900
C28 H28B 0.9900
C29 C30 1.517(2)
C29 H29A 0.9900
C29 H29B 0.9900
C30 C31 1.522(2)
C30 H30A 0.9900
C30 H30B 0.9900
C31 C32 1.518(3)
C31 H31A 0.9900
C31 H31B 0.9900
C32 C33 1.510(3)
C32 H32A 0.9900
C32 H32B 0.9900
C33 C34 1.518(3)
C33 H33A 0.9900
C33 H33B 0.9900
C34 C35 1.508(3)
C34 H34A 0.9900
C34 H34B 0.9900
C35 H35A 0.9800
C35 H35B 0.9800
C35 H35C 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
C6 C1 C2 C3 -3.5(2)
N1 C1 C2 C3 174.25(14)
C1 C2 C3 C4 -0.5(3)
C2 C3 C4 C5 2.6(3)
C3 C4 C5 C6 -0.7(3)
C2 C1 C6 N2 -176.69(15)
N1 C1 C6 N2 5.5(2)
C2 C1 C6 C5 5.2(2)
N1 C1 C6 C5 -172.62(13)
C4 C5 C6 N2 178.64(14)
C4 C5 C6 C1 -3.1(2)
C17 C8 C9 C10 175.73(14)
S1 C8 C9 C10 -3.10(17)
N2 C7 C10 C11 -20.6(3)
S1 C7 C10 C11 167.61(11)
N2 C7 C10 C9 167.02(16)
S1 C7 C10 C9 -4.78(15)
C8 C9 C10 C11 -166.49(15)
C8 C9 C10 C7 5.24(19)
C7 C10 C11 N3 159.68(14)
C9 C10 C11 N3 -29.2(3)
C7 C10 C11 N1 -21.0(2)
C9 C10 C11 N1 150.07(14)
N3 C12 C13 N4 -52.60(17)
N4 C14 C15 N3 57.44(16)
O4 C20 C21 C22 -9.3(3)
O3 C20 C21 C22 170.14(14)
C20 C21 C22 C23 178.47(15)
C21 C22 C23 C24 175.46(16)
C22 C23 C24 C25 178.44(16)
C23 C24 C25 C26 170.90(16)
C24 C25 C26 C27 -175.63(17)
C25 C26 C27 C28 177.51(17)
C26 C27 C28 C29 -176.57(17)
C27 C28 C29 C30 178.76(17)
C28 C29 C30 C31 -177.93(17)
C29 C30 C31 C32 -178.14(17)
C30 C31 C32 C33 -178.70(17)
C31 C32 C33 C34 -178.69(17)
C32 C33 C34 C35 -177.9(2)
O1 C18 N1 C11 159.93(14)
O2 C18 N1 C11 -23.21(17)
O1 C18 N1 C1 8.8(2)
O2 C18 N1 C1 -174.32(12)
N3 C11 N1 C18 104.27(15)
C10 C11 N1 C18 -75.13(17)
N3 C11 N1 C1 -103.48(15)
C10 C11 N1 C1 77.12(16)
C2 C1 N1 C18 -95.20(17)
C6 C1 N1 C18 82.63(17)
C2 C1 N1 C11 112.32(15)
C6 C1 N1 C11 -69.85(17)
C10 C7 N2 C6 1.3(3)
S1 C7 N2 C6 172.73(11)
C1 C6 N2 C7 26.8(2)
C5 C6 N2 C7 -155.04(15)
C10 C11 N3 C12 -9.6(2)
N1 C11 N3 C12 171.05(13)
C10 C11 N3 C15 157.69(15)
N1 C11 N3 C15 -21.6(2)
C13 C12 N3 C11 -142.43(14)
C13 C12 N3 C15 49.21(17)
C14 C15 N3 C11 139.84(14)
C14 C15 N3 C12 -51.78(17)
C15 C14 N4 C16 175.40(13)
C15 C14 N4 C13 -61.24(16)
C12 C13 N4 C16 -177.43(14)
C12 C13 N4 C14 58.94(17)
O1 C18 O2 C19 -16.2(2)
N1 C18 O2 C19 166.86(12)
O3 C19 O2 C18 -85.34(16)
O4 C20 O3 C19 -11.4(2)
C21 C20 O3 C19 169.17(13)
O2 C19 O3 C20 -99.31(16)
C9 C8 S1 C7 0.18(12)
C17 C8 S1 C7 -178.77(12)
N2 C7 S1 C8 -170.93(12)
C10 C7 S1 C8 2.69(11)