#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:24:42 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268652 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/31/7243195.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_7243195
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 H19 N4 O S, C4 H3 O4, C2 H2 O2'
_chemical_formula_sum            'C28 H24 N4 O7 S'
_chemical_formula_weight         560.57
_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
_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                102.579(3)
_cell_angle_beta                 105.605(3)
_cell_angle_gamma                93.678(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1582(3)
_cell_length_b                   13.1348(4)
_cell_length_c                   13.1911(4)
_cell_measurement_reflns_used    10693
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.8570
_cell_measurement_theta_min      3.4630
_cell_volume                     1317.35(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     52.00  88.00   0.50    0.50    --    0.00  57.00 -30.00   72
  2  ω    -21.00  51.00   0.50    0.50    --    0.00  77.00 150.00  144
  3  ω     56.00  88.00   0.50    0.50    --    0.00  77.00 150.00   64
  4  ω    -22.00  22.00   0.50    0.50    --    0.00  57.00 -30.00   88
  5  ω    -88.00  27.00   0.50    0.50    --    0.00 -57.00  90.00  230
  6  ω     93.00 133.00   0.50    1.00    --  106.20 -82.00  60.00   80
  7  ω     20.00 132.00   0.50    1.00    --  106.20 -45.00-180.00  224
  8  ω     62.00 122.00   0.50    1.00    --  106.20 -82.00 -30.00  120
  9  ω     86.00 171.00   0.50    1.00    --  106.20  30.00  60.00  170
 10  ω     73.00 146.00   0.50    1.00    --  106.20  30.00 150.00  146
 11  ω     18.00 141.00   0.50    1.00    --  106.20 -82.00-150.00  246
 12  ω     29.00  55.00   0.50    1.00    --  106.20 -82.00  60.00   52
 13  ω     18.00 126.00   0.50    1.00    --  106.20 -82.00  90.00  216
 14  ω     18.00 134.00   0.50    1.00    --  106.20 -61.00 -30.00  232
 15  ω     25.00  52.00   0.50    1.00    --  106.20 -82.00 -90.00   54
 16  ω     78.00 153.00   0.50    1.00    --  106.20  45.00-180.00  150
 17  ω    109.00 194.00   0.50    1.00    --  106.20  30.00 120.00  170
 18  ω     75.00 135.00   0.50    1.00    --  106.20 -82.00 -90.00  120
 19  ω     30.00  55.00   0.50    1.00    --  106.20 -82.00-180.00   50
 20  ω    150.00 195.00   0.50    1.00    --  106.20  30.00 150.00   90
 21  ω     44.00  70.00   0.50    1.00    --  106.20 -82.00 150.00   52
 22  ω     91.00 126.00   0.50    1.00    --  106.20 -82.00 150.00   70
 23  ω    106.00 131.00   0.50    1.00    --  106.20 -82.00   0.00   50
 24  ω     48.00  74.00   0.50    1.00    --  106.20 -82.00 120.00   52
 25  ω    105.00 132.00   0.50    1.00    --  106.20 -82.00 120.00   54
 26  ω     20.00  85.00   0.50    1.00    --  106.20 -61.00 -90.00  130
 27  ω     25.00  50.00   0.50    1.00    --  106.20 -82.00 -30.00   50
 28  ω    127.00 180.00   0.50    1.00    --  106.20  30.00  30.00  106
;
_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      -0.0837582000
_diffrn_orient_matrix_UB_12      0.0877422000
_diffrn_orient_matrix_UB_13      -0.0475212000
_diffrn_orient_matrix_UB_21      0.1759287000
_diffrn_orient_matrix_UB_22      0.0461741000
_diffrn_orient_matrix_UB_23      -0.0039824000
_diffrn_orient_matrix_UB_31      -0.0337823000
_diffrn_orient_matrix_UB_32      -0.0697223000
_diffrn_orient_matrix_UB_33      -0.1156055000
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.602
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83193
_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            Yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0468
_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)+(0.0593P)²+0.7153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4972
_reflns_number_total             5560
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00620g2.cif
_cod_data_source_block           axitinib_fumaricacid
_cod_depositor_comments
'Adding full bibliography for 7243193--7243195.cif.'
_cod_database_code               7243195
_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.
;
_reflns_odcompleteness_completeness 99.35
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C6(H6), C7(H7), C24(H24), C19(H19), C13(H13), C16(H16),
 C4(H4A), C11(H11), C14(H14), C17(H17), C1(H1A), C18(H18), C3(H3A), C28(H28),
 C2(H2), C25(H25)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6A)
;
_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.773
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 0.03270(6) 0.67414(4) 0.97106(4) 0.03262(13) Uani 1 1 d . . . . .
O3 O 0.36427(18) 0.75305(10) 0.60306(11) 0.0360(3) Uani 1 1 d . . . . .
O1 O -0.00570(17) 0.80277(11) 1.16969(11) 0.0374(3) Uani 1 1 d . . . . .
O5 O 0.1841(2) 1.10036(10) 0.56638(12) 0.0417(3) Uani 1 1 d . . . . .
H5 H 0.169676 1.162429 0.573329 0.063 Uiso 1 1 calc R U . . .
O2 O 0.3270(2) 0.74684(11) 0.42781(11) 0.0422(3) Uani 1 1 d . . . . .
O6 O 0.34559(19) 0.85899(12) 0.78573(12) 0.0415(3) Uani 1 1 d . . . . .
H6A H 0.372230 0.827257 0.732947 0.062 Uiso 1 1 calc R U . . .
O7 O 0.62961(19) 0.89819(12) 0.85798(13) 0.0456(4) Uani 1 1 d . . . . .
N1 N 0.35402(19) 0.55910(12) 0.33927(12) 0.0287(3) Uani 1 1 d . . . . .
N3 N 0.0823(2) 0.32657(12) 0.70803(13) 0.0332(3) Uani 1 1 d . . . . .
H3 H 0.052696 0.280768 0.739685 0.040 Uiso 1 1 calc R U . . .
O4 O 0.2653(3) 1.12433(12) 0.42338(14) 0.0582(5) Uani 1 1 d . . . . .
N2 N 0.1286(2) 0.30290(12) 0.61626(13) 0.0329(3) Uani 1 1 d . . . . .
N4 N 0.1198(2) 0.96337(14) 1.18111(18) 0.0471(5) Uani 1 1 d . . . . .
H4 H 0.207496 1.000838 1.177510 0.056 Uiso 1 1 calc R U . . .
C20 C 0.2693(2) 0.81697(14) 1.13848(14) 0.0276(3) Uani 1 1 d . . . . .
C23 C 0.3296(2) 0.79292(14) 0.52243(15) 0.0309(4) Uani 1 1 d . . . . .
C9 C 0.1413(2) 0.47970(13) 0.67103(14) 0.0273(3) Uani 1 1 d . . . . .
C5 C 0.3221(2) 0.46643(13) 0.36425(14) 0.0273(3) Uani 1 1 d . . . . .
C21 C 0.1169(2) 0.86089(15) 1.16498(15) 0.0310(4) Uani 1 1 d . . . . .
C15 C 0.2460(2) 0.72986(13) 1.05018(14) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.2718(2) 0.47288(14) 0.46296(14) 0.0293(4) Uani 1 1 d . . . . .
H6 H 0.273312 0.539408 0.506017 0.035 Uiso 1 1 calc R U . . .
C10 C 0.0881(2) 0.43188(14) 0.74438(15) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.1662(2) 0.39360(13) 0.59139(14) 0.0285(4) Uani 1 1 d . . . . .
C7 C 0.2234(2) 0.38952(14) 0.49590(15) 0.0306(4) Uani 1 1 d . . . . .
H7 H 0.226881 0.323322 0.453957 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2862(2) 0.90303(14) 0.53889(15) 0.0318(4) Uani 1 1 d . . . . .
H24 H 0.262405 0.933339 0.603077 0.038 Uiso 1 1 calc R U . . .
C12 C 0.0730(2) 0.59627(14) 0.85405(15) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.4354(2) 0.86082(14) 1.20139(15) 0.0311(4) Uani 1 1 d . . . . .
H19 H 0.450949 0.917892 1.260427 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1212(2) 0.64660(14) 0.77949(15) 0.0319(4) Uani 1 1 d . . . . .
H13 H 0.128628 0.719453 0.791991 0.038 Uiso 1 1 calc R U . . .
C27 C 0.4844(2) 0.90327(14) 0.86379(15) 0.0323(4) Uani 1 1 d . . . . .
C16 C 0.3907(2) 0.69109(15) 1.02691(15) 0.0322(4) Uani 1 1 d . . . . .
H16 H 0.376789 0.633922 0.968205 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3370(2) 0.37355(14) 0.29401(15) 0.0317(4) Uani 1 1 d . . . . .
H4A H 0.317856 0.309032 0.309929 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0546(2) 0.48891(14) 0.83817(15) 0.0304(4) Uani 1 1 d . . . . .
H11 H 0.021958 0.455902 0.886626 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1570(2) 0.59020(14) 0.68981(15) 0.0305(4) Uani 1 1 d . . . . .
H14 H 0.190906 0.623907 0.642249 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5546(2) 0.73652(16) 1.08995(16) 0.0355(4) Uani 1 1 d . . . . .
H17 H 0.649507 0.709872 1.073018 0.043 Uiso 1 1 calc R U . . .
C1 C 0.3958(2) 0.56459(15) 0.24909(16) 0.0337(4) Uani 1 1 d . . . . .
H1A H 0.416210 0.629824 0.234926 0.040 Uiso 1 1 calc R U . . .
C26 C 0.2425(3) 1.06917(15) 0.48203(16) 0.0367(4) Uani 1 1 d . . . . .
C18 C 0.5780(2) 0.82119(16) 1.17783(15) 0.0345(4) Uani 1 1 d . . . . .
H18 H 0.688019 0.851218 1.220647 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3804(3) 0.37808(15) 0.20090(16) 0.0361(4) Uani 1 1 d . . . . .
H3A H 0.390670 0.316450 0.153876 0.043 Uiso 1 1 calc R U . . .
C28 C 0.4444(3) 0.96258(15) 0.96258(16) 0.0361(4) Uani 1 1 d . . . . .
H28 H 0.337490 0.946262 0.971700 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4089(3) 0.47459(16) 0.17709(16) 0.0368(4) Uani 1 1 d . . . . .
H2 H 0.436278 0.478202 0.113816 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2802(3) 0.95884(15) 0.46727(16) 0.0375(4) Uani 1 1 d . . . . .
H25 H 0.301050 0.927037 0.402516 0.045 Uiso 1 1 calc R U . . .
C22 C -0.0237(3) 1.0144(2) 1.2050(3) 0.0722(9) Uani 1 1 d . . . . .
H22A H -0.127480 0.983893 1.148409 0.108 Uiso 1 1 calc R U . . .
H22B H -0.003103 1.088244 1.209407 0.108 Uiso 1 1 calc R U . . .
H22C H -0.034848 1.004686 1.273028 0.108 Uiso 1 1 calc R U . . .
H1 H 0.341(4) 0.632(2) 0.388(2) 0.068(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 100.54(8) . . ?
C26 O5 H5 109.5 . . ?
C27 O6 H6A 109.5 . . ?
C5 N1 H1 122.2(16) . . ?
C1 N1 C5 122.52(16) . . ?
C1 N1 H1 115.2(16) . . ?
N2 N3 H3 124.3 . . ?
N2 N3 C10 111.32(15) . . ?
C10 N3 H3 124.3 . . ?
C8 N2 N3 107.61(15) . . ?
C21 N4 H4 119.6 . . ?
C21 N4 C22 120.87(19) . . ?
C22 N4 H4 119.6 . . ?
C15 C20 C21 120.05(16) . . ?
C19 C20 C21 120.70(16) . . ?
C19 C20 C15 119.25(16) . . ?
O3 C23 C24 118.23(16) . . ?
O2 C23 O3 124.98(17) . . ?
O2 C23 C24 116.78(16) . . ?
C10 C9 C8 104.34(15) . . ?
C10 C9 C14 118.92(16) . . ?
C14 C9 C8 136.74(17) . . ?
N1 C5 C6 116.15(15) . . ?
N1 C5 C4 118.50(17) . . ?
C4 C5 C6 125.35(17) . . ?
O1 C21 N4 122.50(18) . . ?
O1 C21 C20 121.32(17) . . ?
N4 C21 C20 116.17(16) . . ?
C20 C15 S1 118.70(13) . . ?
C16 C15 S1 122.53(14) . . ?
C16 C15 C20 118.76(16) . . ?
C5 C6 H6 117.8 . . ?
C7 C6 C5 124.34(16) . . ?
C7 C6 H6 117.8 . . ?
N3 C10 C9 107.33(16) . . ?
N3 C10 C11 129.39(17) . . ?
C11 C10 C9 123.26(16) . . ?
N2 C8 C9 109.39(16) . . ?
N2 C8 C7 118.47(16) . . ?
C9 C8 C7 132.13(16) . . ?
C6 C7 C8 125.52(17) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C23 C24 H24 118.4 . . ?
C25 C24 C23 123.14(17) . . ?
C25 C24 H24 118.4 . . ?
C13 C12 S1 119.30(14) . . ?
C11 C12 S1 118.70(14) . . ?
C11 C12 C13 122.00(17) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.41(17) . . ?
C18 C19 H19 119.3 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.34(17) . . ?
C14 C13 H13 119.3 . . ?
O6 C27 C28 112.08(17) . . ?
O7 C27 O6 124.81(18) . . ?
O7 C27 C28 123.11(18) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.00(17) . . ?
C17 C16 H16 119.5 . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 C5 119.58(18) . . ?
C3 C4 H4A 120.2 . . ?
C10 C11 H11 122.0 . . ?
C12 C11 C10 115.97(16) . . ?
C12 C11 H11 122.0 . . ?
C9 C14 H14 120.8 . . ?
C13 C14 C9 118.46(17) . . ?
C13 C14 H14 120.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.37(18) . . ?
C18 C17 H17 119.8 . . ?
N1 C1 H1A 119.7 . . ?
N1 C1 C2 120.58(18) . . ?
C2 C1 H1A 119.7 . . ?
O5 C26 C25 112.76(16) . . ?
O4 C26 O5 124.15(18) . . ?
O4 C26 C25 123.09(19) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.19(17) . . ?
C17 C18 H18 120.4 . . ?
C4 C3 H3A 119.9 . . ?
C4 C3 C2 120.17(17) . . ?
C2 C3 H3A 119.9 . . ?
C27 C28 H28 118.9 . . ?
C28 C28 C27 122.3(2) 2_677 . ?
C28 C28 H28 118.9 2_677 . ?
C1 C2 C3 118.63(18) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C24 C25 C26 124.66(18) . . ?
C24 C25 H25 117.7 . . ?
C26 C25 H25 117.7 . . ?
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 . . ?
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 1.7832(18) . ?
S1 C12 1.7789(19) . ?
O3 C23 1.259(2) . ?
O1 C21 1.242(2) . ?
O5 H5 0.8200 . ?
O5 C26 1.321(2) . ?
O2 C23 1.257(2) . ?
O6 H6A 0.8200 . ?
O6 C27 1.307(2) . ?
O7 C27 1.212(2) . ?
N1 C5 1.356(2) . ?
N1 C1 1.338(2) . ?
N1 H1 1.06(3) . ?
N3 H3 0.8600 . ?
N3 N2 1.343(2) . ?
N3 C10 1.355(2) . ?
O4 C26 1.209(2) . ?
N2 C8 1.341(2) . ?
N4 H4 0.8600 . ?
N4 C21 1.314(3) . ?
N4 C22 1.458(3) . ?
C20 C21 1.497(2) . ?
C20 C15 1.405(2) . ?
C20 C19 1.394(3) . ?
C23 C24 1.495(2) . ?
C9 C10 1.406(2) . ?
C9 C8 1.432(2) . ?
C9 C14 1.409(2) . ?
C5 C6 1.454(3) . ?
C5 C4 1.396(2) . ?
C15 C16 1.397(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.337(3) . ?
C10 C11 1.404(3) . ?
C8 C7 1.448(3) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.309(3) . ?
C12 C13 1.421(3) . ?
C12 C11 1.372(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C27 C28 1.494(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(3) . ?
C4 H4A 0.9300 . ?
C4 C3 1.379(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(3) . ?
C26 C25 1.483(3) . ?
C18 H18 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C2 1.391(3) . ?
C28 C28 1.321(4) 2_677 ?
C28 H28 0.9300 . ?
C2 H2 0.9300 . ?
C25 H25 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
O5 H5 N2 0.82 1.89 2.696(2) 168.3 1_565
O6 H6A O3 0.82 1.76 2.5554(19) 163.3 .
N3 H3 O1 0.86 1.88 2.735(2) 170.6 2_567
N4 H4 O7 0.86 2.03 2.872(2) 165.9 2_677
N1 H1 O2 1.06(3) 1.51(3) 2.5391(19) 163(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 179.81(14) . . . . ?
S1 C12 C13 C14 178.57(14) . . . . ?
S1 C12 C11 C10 179.96(13) . . . . ?
O3 C23 C24 C25 166.6(2) . . . . ?
O5 C26 C25 C24 -11.8(3) . . . . ?
O2 C23 C24 C25 -13.9(3) . . . . ?
O6 C27 C28 C28 -159.4(2) . . . 2_677 ?
O7 C27 C28 C28 20.2(4) . . . 2_677 ?
N1 C5 C6 C7 174.92(17) . . . . ?
N1 C5 C4 C3 -1.2(3) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
N3 N2 C8 C9 -0.4(2) . . . . ?
N3 N2 C8 C7 178.86(15) . . . . ?
N3 C10 C11 C12 179.35(18) . . . . ?
O4 C26 C25 C24 167.4(2) . . . . ?
N2 N3 C10 C9 0.2(2) . . . . ?
N2 N3 C10 C11 -177.96(17) . . . . ?
N2 C8 C7 C6 -177.27(18) . . . . ?
C20 C15 C16 C17 0.7(3) . . . . ?
C20 C19 C18 C17 0.1(3) . . . . ?
C23 C24 C25 C26 -178.21(19) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C9 C8 C7 C6 1.8(3) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
C5 C6 C7 C8 -177.38(16) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C21 C20 C15 S1 0.3(2) . . . . ?
C21 C20 C15 C16 179.52(16) . . . . ?
C21 C20 C19 C18 -179.89(17) . . . . ?
C15 S1 C12 C13 -73.04(16) . . . . ?
C15 S1 C12 C11 107.60(15) . . . . ?
C15 C20 C21 O1 47.3(3) . . . . ?
C15 C20 C21 N4 -131.69(19) . . . . ?
C15 C20 C19 C18 0.9(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C6 C5 C4 C3 177.82(17) . . . . ?
C10 N3 N2 C8 0.2(2) . . . . ?
C10 C9 C8 N2 0.53(19) . . . . ?
C10 C9 C8 C7 -178.63(18) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C8 C9 C10 N3 -0.42(19) . . . . ?
C8 C9 C10 C11 177.86(16) . . . . ?
C8 C9 C14 C13 -179.38(19) . . . . ?
C12 S1 C15 C20 164.53(14) . . . . ?
C12 S1 C15 C16 -14.63(17) . . . . ?
C12 C13 C14 C9 1.4(3) . . . . ?
C19 C20 C21 O1 -131.91(19) . . . . ?
C19 C20 C21 N4 49.1(3) . . . . ?
C19 C20 C15 S1 179.59(13) . . . . ?
C19 C20 C15 C16 -1.2(3) . . . . ?
C13 C12 C11 C10 0.6(3) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C4 C5 C6 C7 -4.1(3) . . . . ?
C4 C3 C2 C1 1.1(3) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C14 C9 C10 N3 179.58(16) . . . . ?
C14 C9 C10 C11 -2.1(3) . . . . ?
C14 C9 C8 N2 -179.5(2) . . . . ?
C14 C9 C8 C7 1.4(4) . . . . ?
C1 N1 C5 C6 -177.72(16) . . . . ?
C1 N1 C5 C4 1.4(3) . . . . ?
C22 N4 C21 O1 -0.4(4) . . . . ?
C22 N4 C21 C20 178.6(2) . . . . ?
