#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:24:42 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268652 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/31/7243193.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_7243193
loop_
_publ_author_name
'Ren, Bo-Ying'
'Dai, Xia-Lin'
'Wang, Jie'
'Wu, Chao'
'Lu, Tong-Bu'
'Chen, Jia-Mei'
_publ_section_title
;
 Cocrystallization of axitinib with carboxylic acids: preparation, crystal
 structures and dissolution behavior
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              5504
_journal_page_last               5515
_journal_paper_doi               10.1039/D1CE00620G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 N4 O S, C8 H14 O4'
_chemical_formula_sum            'C30 H32 N4 O5 S'
_chemical_formula_weight         560.65
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                112.959(2)
_cell_angle_beta                 92.287(2)
_cell_angle_gamma                96.7660(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9380(2)
_cell_length_b                   13.3534(2)
_cell_length_c                   14.1943(2)
_cell_measurement_reflns_used    11807
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.2050
_cell_measurement_theta_min      3.6220
_cell_volume                     1369.67(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00   6.00   0.50    0.50    --    0.00 -57.00-150.00   82
  2  ω    -51.00 -19.00   0.50    0.50    --    0.00 -57.00-180.00   64
  3  ω    -29.00  89.00   0.50    0.50    --    0.00  37.00  90.00  236
  4  ω    -83.00 -58.00   0.50    0.50    --    0.00 -37.00  90.00   50
  5  ω    -55.00  27.00   0.50    0.50    --    0.00 -37.00  90.00  164
  6  ω    -14.00  12.00   0.50    0.50    --    0.00 -57.00 -90.00   52
  7  ω     29.00 106.00   0.50    1.00    --  106.20 -61.00 150.00  154
  8  ω     33.00 127.00   0.50    1.00    --  106.20 -45.00   0.00  188
  9  ω     76.00 117.00   0.50    1.00    --  106.20 -82.00-150.00   82
 10  ω     28.00  57.00   0.50    1.00    --  106.20 -82.00 120.00   58
 11  ω     93.00 141.00   0.50    1.00    --  106.20 -82.00 120.00   96
 12  ω     17.00 135.00   0.50    1.00    --  106.20 -45.00 -90.00  236
 13  ω     17.00 140.00   0.50    1.00    --  106.20 -82.00 -90.00  246
 14  ω     18.00  66.00   0.50    1.00    --  106.20 -45.00-150.00   96
 15  ω     17.00 107.00   0.50    1.00    --  106.20 -61.00 -90.00  180
 16  ω     23.00 139.00   0.50    1.00    --  106.20 -30.00  90.00  232
 17  ω     62.00 138.00   0.50    1.00    --  106.20 -82.00  60.00  152
 18  ω    123.00 165.00   0.50    1.00    --  106.20  30.00-150.00   84
 19  ω     88.00 114.00   0.50    1.00    --  106.20 -82.00 -60.00   52
 20  ω     88.00 124.00   0.50    1.00    --  106.20  45.00  90.00   72
 21  ω    126.00 152.00   0.50    1.00    --  106.20  61.00 -60.00   52
 22  ω     50.00 140.00   0.50    1.00    --  106.20 -77.00  30.00  180
 23  ω     74.00  99.00   0.50    1.00    --  106.20 -82.00-180.00   50
 24  ω     20.00 195.00   0.50    1.00    --  106.20 -15.00   0.00  350
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0230895000
_diffrn_orient_matrix_UB_12      -0.1095686000
_diffrn_orient_matrix_UB_13      -0.0951264000
_diffrn_orient_matrix_UB_21      -0.0400495000
_diffrn_orient_matrix_UB_22      0.0607634000
_diffrn_orient_matrix_UB_23      -0.0689660000
_diffrn_orient_matrix_UB_31      0.1907804000
_diffrn_orient_matrix_UB_32      0.0183834000
_diffrn_orient_matrix_UB_33      -0.0145520000
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16178
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.502
_diffrn_reflns_theta_min         3.397
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0886P)²+0.3612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5151
_reflns_number_total             5562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00620g2.cif
_cod_data_source_block           axitinib_subericacid
_cod_depositor_comments
'Adding full bibliography for 7243193--7243195.cif.'
_cod_database_code               7243193
_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_max   0.869
_shelx_estimated_absorpt_t_min   0.532
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C26(H26A,
 H26B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), C13(H13), C3(H3A), C14(H14), C7(H7), C4(H4A), C6(H6),
 C18(H18), C11(H11), C16(H16), C1(H1), C2(H2), C19(H19), C17(H17)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.580
_oxdiff_exptl_absorpt_empirical_full_min 0.475
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 0.86932(5) 0.12400(3) 0.44561(3) 0.02428(14) Uani 1 1 d . . . . .
O1 O 0.85158(15) -0.00326(10) 0.23450(9) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.62042(17) 0.66937(11) 1.03686(10) 0.0239(3) Uani 1 1 d . . . . .
N2 N 0.93738(17) 0.25468(11) 0.92004(10) 0.0229(3) Uani 1 1 d . . . . .
N4 N 0.69385(18) 0.05159(12) 0.13208(10) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.609494 0.084475 0.126510 0.031 Uiso 1 1 calc R U . . .
N3 N 0.97179(18) 0.17986(11) 0.82892(10) 0.0238(3) Uani 1 1 d . . . . .
H3 H 1.017641 0.122452 0.821987 0.029 Uiso 1 1 calc R U . . .
C21 C 0.7263(2) 0.03775(12) 0.21880(11) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.8095(2) 0.29966(14) 0.62217(12) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.775719 0.331405 0.578015 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5993(2) 0.06890(12) 0.29646(11) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.86739(19) 0.33212(12) 0.90085(12) 0.0211(3) Uani 1 1 d . . . . .
C22 C 0.7979(2) 0.01231(16) 0.04698(13) 0.0333(4) Uani 1 1 d . . . . .
H22A H 0.777561 0.046807 0.000420 0.050 Uiso 1 1 calc R U . . .
H22B H 0.769014 -0.065930 0.011521 0.050 Uiso 1 1 calc R U . . .
H22C H 0.916063 0.030060 0.072678 0.050 Uiso 1 1 calc R U . . .
C9 C 0.85815(19) 0.30638(12) 0.79218(11) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.6909(2) 0.59518(12) 1.06298(12) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.92477(19) 0.20687(13) 0.74965(12) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.6487(2) 0.69471(14) 1.23973(13) 0.0294(4) Uani 1 1 d . . . . .
H3A H 0.657293 0.703077 1.308009 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6488(2) 0.10252(12) 0.40216(12) 0.0214(3) Uani 1 1 d . . . . .
C14 C 0.8014(2) 0.35414(13) 0.72619(12) 0.0241(3) Uani 1 1 d . . . . .
H14 H 0.759459 0.420904 0.752343 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8138(2) 0.42159(13) 0.98542(12) 0.0230(3) Uani 1 1 d . . . . .
H7 H 0.828360 0.421124 1.050579 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8683(2) 0.19588(13) 0.58071(12) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.7068(2) 0.60667(13) 1.16523(12) 0.0250(3) Uani 1 1 d . . . . .
H4A H 0.755756 0.555720 1.182910 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7447(2) 0.50504(13) 0.97740(12) 0.0238(3) Uani 1 1 d . . . . .
H6 H 0.729980 0.505590 0.912281 0.029 Uiso 1 1 calc R U . . .
C18 C 0.3033(2) 0.07592(14) 0.33286(14) 0.0295(4) Uani 1 1 d . . . . .
H18 H 0.189333 0.069010 0.310118 0.035 Uiso 1 1 calc R U . . .
C11 C 0.93025(19) 0.14905(13) 0.64348(11) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.973408 0.082731 0.616996 0.026 Uiso 1 1 calc R U . . .
C16 C 0.5230(2) 0.11890(14) 0.47083(13) 0.0284(4) Uani 1 1 d . . . . .
H16 H 0.553739 0.138544 0.540303 0.034 Uiso 1 1 calc R U . . .
C1 C 0.5658(2) 0.75478(13) 1.10974(13) 0.0266(3) Uani 1 1 d . . . . .
H1 H 0.518115 0.805321 1.090755 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5774(2) 0.77069(14) 1.21209(13) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.538567 0.830763 1.261294 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4267(2) 0.05616(13) 0.26388(13) 0.0255(3) Uani 1 1 d . . . . .
H19 H 0.393798 0.033905 0.194267 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3523(2) 0.10606(15) 0.43605(14) 0.0318(4) Uani 1 1 d . . . . .
H17 H 0.270115 0.117862 0.482644 0.038 Uiso 1 1 calc R U . . .
O4 O -0.0488(2) 0.38619(14) 0.18611(10) 0.0543(5) Uani 1 1 d . . . . .
O5 O 0.05957(19) 0.23586(11) 0.09684(9) 0.0373(3) Uani 1 1 d . . . . .
H5 H 0.015690 0.245332 0.048250 0.056 Uiso 1 1 calc R U . . .
O2 O 0.53655(17) 0.61691(10) 0.84383(9) 0.0304(3) Uani 1 1 d . . . . .
O3 O 0.48560(18) 0.78911(10) 0.89154(9) 0.0338(3) Uani 1 1 d . . . . .
C30 C 0.0267(2) 0.31189(13) 0.18322(12) 0.0250(3) Uani 1 1 d . . . . .
C29 C 0.0938(2) 0.29912(14) 0.27859(12) 0.0272(3) Uani 1 1 d . . . . .
H29A H 0.185718 0.255044 0.262598 0.033 Uiso 1 1 calc R U . . .
H29B H 0.003651 0.261593 0.302208 0.033 Uiso 1 1 calc R U . . .
C25 C 0.3471(2) 0.54415(13) 0.65036(12) 0.0247(3) Uani 1 1 d . . . . .
H25A H 0.439023 0.501290 0.646662 0.030 Uiso 1 1 calc R U . . .
H25B H 0.255362 0.517717 0.681720 0.030 Uiso 1 1 calc R U . . .
C27 C 0.2152(2) 0.41255(13) 0.46762(12) 0.0252(3) Uani 1 1 d . . . . .
H27A H 0.119469 0.383451 0.494338 0.030 Uiso 1 1 calc R U . . .
H27B H 0.303330 0.366131 0.460016 0.030 Uiso 1 1 calc R U . . .
C28 C 0.1585(2) 0.41184(13) 0.36301(12) 0.0247(3) Uani 1 1 d . . . . .
H28A H 0.068907 0.457400 0.372126 0.030 Uiso 1 1 calc R U . . .
H28B H 0.253986 0.445615 0.339840 0.030 Uiso 1 1 calc R U . . .
C23 C 0.4795(2) 0.69582(13) 0.82557(12) 0.0239(3) Uani 1 1 d . . . . .
C26 C 0.2837(2) 0.52996(13) 0.54259(12) 0.0238(3) Uani 1 1 d . . . . .
H26A H 0.376689 0.558185 0.513303 0.029 Uiso 1 1 calc R U . . .
H26B H 0.194142 0.574995 0.548297 0.029 Uiso 1 1 calc R U . . .
C24 C 0.4104(2) 0.66547(13) 0.71578(12) 0.0254(3) Uani 1 1 d . . . . .
H24A H 0.499144 0.690287 0.681493 0.030 Uiso 1 1 calc R U . . .
H24B H 0.316899 0.706448 0.716854 0.030 Uiso 1 1 calc R U . . .
H2A H 0.573(4) 0.642(3) 0.918(3) 0.073(9) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C15 102.11(7) . . ?
C1 N1 C5 119.68(14) . . ?
C8 N2 N3 107.38(12) . . ?
C21 N4 H4 119.3 . . ?
C21 N4 C22 121.34(14) . . ?
C22 N4 H4 119.3 . . ?
N2 N3 H3 124.3 . . ?
N2 N3 C10 111.48(12) . . ?
C10 N3 H3 124.3 . . ?
O1 C21 N4 122.81(14) . . ?
O1 C21 C20 120.18(14) . . ?
N4 C21 C20 116.95(13) . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.45(15) . . ?
C12 C13 H13 119.3 . . ?
C15 C20 C21 120.98(14) . . ?
C19 C20 C21 119.78(14) . . ?
C19 C20 C15 119.04(14) . . ?
N2 C8 C9 109.45(13) . . ?
N2 C8 C7 119.01(14) . . ?
C9 C8 C7 131.53(14) . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C9 C8 104.58(13) . . ?
C10 C9 C14 118.89(14) . . ?
C14 C9 C8 136.53(14) . . ?
N1 C5 C4 120.68(15) . . ?
N1 C5 C6 115.04(14) . . ?
C4 C5 C6 124.28(15) . . ?
N3 C10 C9 107.09(13) . . ?
N3 C10 C11 129.58(14) . . ?
C11 C10 C9 123.28(14) . . ?
C4 C3 H3A 120.2 . . ?
C4 C3 C2 119.66(16) . . ?
C2 C3 H3A 120.2 . . ?
C20 C15 S1 119.61(12) . . ?
C16 C15 S1 121.40(12) . . ?
C16 C15 C20 118.99(15) . . ?
C13 C14 C9 118.44(14) . . ?
C13 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
C8 C7 H7 117.4 . . ?
C6 C7 C8 125.21(14) . . ?
C6 C7 H7 117.4 . . ?
C13 C12 S1 120.80(12) . . ?
C11 C12 S1 117.83(12) . . ?
C11 C12 C13 121.35(15) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 C5 119.15(15) . . ?
C3 C4 H4A 120.4 . . ?
C5 C6 H6 117.5 . . ?
C7 C6 C5 125.01(15) . . ?
C7 C6 H6 117.5 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.02(16) . . ?
C10 C11 H11 121.8 . . ?
C12 C11 C10 116.42(14) . . ?
C12 C11 H11 121.8 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.56(16) . . ?
C17 C16 H16 119.7 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.47(16) . . ?
C2 C1 H1 118.8 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.36(16) . . ?
C1 C2 H2 120.8 . . ?
C20 C19 H19 119.2 . . ?
C18 C19 C20 121.59(15) . . ?
C18 C19 H19 119.2 . . ?
C18 C17 C16 120.74(16) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C30 O5 H5 109.5 . . ?
C23 O2 H2A 110.2(18) . . ?
O4 C30 O5 122.72(15) . . ?
O4 C30 C29 123.09(15) . . ?
O5 C30 C29 114.18(14) . . ?
C30 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
C30 C29 C28 109.93(14) . . ?
H29A C29 H29B 108.2 . . ?
C28 C29 H29A 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C26 C25 H25A 109.7 . . ?
C26 C25 H25B 109.7 . . ?
C26 C25 C24 109.80(13) . . ?
C24 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.7 . . ?
C28 C27 H27B 109.7 . . ?
C26 C27 H27A 109.7 . . ?
C26 C27 H27B 109.7 . . ?
C26 C27 C28 109.80(13) . . ?
C29 C28 C27 115.81(13) . . ?
C29 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C27 C28 H28A 108.3 . . ?
C27 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
O2 C23 C24 115.18(14) . . ?
O3 C23 O2 122.86(15) . . ?
O3 C23 C24 121.93(14) . . ?
C25 C26 C27 116.11(13) . . ?
C25 C26 H26A 108.3 . . ?
C25 C26 H26B 108.3 . . ?
C27 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C25 C24 H24A 107.9 . . ?
C25 C24 H24B 107.9 . . ?
C23 C24 C25 117.55(14) . . ?
C23 C24 H24A 107.9 . . ?
C23 C24 H24B 107.9 . . ?
H24A C24 H24B 107.2 . . ?
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 C15 1.7847(16) . ?
S1 C12 1.7794(16) . ?
O1 C21 1.2425(19) . ?
N1 C5 1.354(2) . ?
N1 C1 1.338(2) . ?
N2 N3 1.3528(18) . ?
N2 C8 1.340(2) . ?
N4 H4 0.8600 . ?
N4 C21 1.334(2) . ?
N4 C22 1.451(2) . ?
N3 H3 0.8600 . ?
N3 C10 1.360(2) . ?
C21 C20 1.495(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(2) . ?
C13 C12 1.422(2) . ?
C20 C15 1.412(2) . ?
C20 C19 1.398(2) . ?
C8 C9 1.440(2) . ?
C8 C7 1.446(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C9 C10 1.405(2) . ?
C9 C14 1.410(2) . ?
C5 C4 1.398(2) . ?
C5 C6 1.459(2) . ?
C10 C11 1.405(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.382(2) . ?
C3 C2 1.390(3) . ?
C15 C16 1.399(2) . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.339(2) . ?
C12 C11 1.378(2) . ?
C4 H4A 0.9300 . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C18 C17 1.384(3) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(2) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C17 H17 0.9300 . ?
O4 C30 1.207(2) . ?
O5 H5 0.8200 . ?
O5 C30 1.311(2) . ?
O2 C23 1.3034(19) . ?
O2 H2A 1.00(3) . ?
O3 C23 1.226(2) . ?
C30 C29 1.513(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C28 1.526(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.523(2) . ?
C25 C24 1.529(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.530(2) . ?
C27 C26 1.529(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C23 C24 1.510(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O3 0.86 2.03 2.8104(19) 151.1 2_666
N3 H3 O1 0.86 1.93 2.7498(17) 159.6 2_756
O5 H5 N2 0.82 1.95 2.7672(18) 171.0 1_454
O2 H2A N1 1.00(3) 1.59(3) 2.5862(18) 173(3) .
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
S1 C15 C16 C17 177.38(13) . . . . ?
S1 C12 C11 C10 -178.87(11) . . . . ?
O1 C21 C20 C15 30.2(2) . . . . ?
O1 C21 C20 C19 -144.49(15) . . . . ?
N1 C5 C4 C3 0.3(2) . . . . ?
N1 C5 C6 C7 -178.43(16) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
N2 N3 C10 C9 0.99(18) . . . . ?
N2 N3 C10 C11 -176.42(15) . . . . ?
N2 C8 C9 C10 1.23(17) . . . . ?
N2 C8 C9 C14 -179.33(17) . . . . ?
N2 C8 C7 C6 178.89(16) . . . . ?
N4 C21 C20 C15 -152.69(14) . . . . ?
N4 C21 C20 C19 32.6(2) . . . . ?
N3 N2 C8 C9 -0.66(17) . . . . ?
N3 N2 C8 C7 178.45(13) . . . . ?
N3 C10 C11 C12 178.00(16) . . . . ?
C21 C20 C15 S1 7.5(2) . . . . ?
C21 C20 C15 C16 -172.83(14) . . . . ?
C21 C20 C19 C18 174.90(15) . . . . ?
C13 C12 C11 C10 2.8(2) . . . . ?
C20 C15 C16 C17 -2.3(2) . . . . ?
C8 N2 N3 C10 -0.20(18) . . . . ?
C8 C9 C10 N3 -1.30(17) . . . . ?
C8 C9 C10 C11 176.30(14) . . . . ?
C8 C9 C14 C13 -177.71(17) . . . . ?
C8 C7 C6 C5 -179.95(15) . . . . ?
C22 N4 C21 O1 4.3(2) . . . . ?
C22 N4 C21 C20 -172.78(15) . . . . ?
C9 C8 C7 C6 -2.2(3) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C5 N1 C1 C2 -0.3(2) . . . . ?
C10 C9 C14 C13 1.7(2) . . . . ?
C15 S1 C12 C13 -61.16(15) . . . . ?
C15 S1 C12 C11 120.50(13) . . . . ?
C15 C20 C19 C18 0.1(2) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C14 C13 C12 S1 177.33(13) . . . . ?
C14 C13 C12 C11 -4.4(3) . . . . ?
C14 C9 C10 N3 179.14(14) . . . . ?
C14 C9 C10 C11 -3.3(2) . . . . ?
C7 C8 C9 C10 -177.73(16) . . . . ?
C7 C8 C9 C14 1.7(3) . . . . ?
C12 S1 C15 C20 166.19(12) . . . . ?
C12 S1 C15 C16 -13.43(15) . . . . ?
C12 C13 C14 C9 2.0(2) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C4 C3 C2 C1 0.5(3) . . . . ?
C6 C5 C4 C3 -178.97(16) . . . . ?
C1 N1 C5 C4 0.2(2) . . . . ?
C1 N1 C5 C6 179.53(14) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C19 C20 C15 S1 -177.73(11) . . . . ?
C19 C20 C15 C16 1.9(2) . . . . ?
C19 C18 C17 C16 1.4(3) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
O4 C30 C29 C28 -36.7(2) . . . . ?
O5 C30 C29 C28 142.55(16) . . . . ?
O2 C23 C24 C25 24.1(2) . . . . ?
O3 C23 C24 C25 -157.94(16) . . . . ?
C30 C29 C28 C27 174.57(14) . . . . ?
C28 C27 C26 C25 -179.43(14) . . . . ?
C26 C25 C24 C23 -179.68(14) . . . . ?
C26 C27 C28 C29 177.55(14) . . . . ?
C24 C25 C26 C27 -179.79(14) . . . . ?
