# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_axitinib_subericacid
_database_code_depnum_ccdc_archive 'CCDC 2022782'
loop_
_audit_author_name
_audit_author_address
'Boying Ren'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N4 O S, C8 H14 O4'
_chemical_formula_sum            'C30 H32 N4 O5 S'
_chemical_formula_weight         560.65
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9380(2)
_cell_length_b                   13.3534(2)
_cell_length_c                   14.1943(2)
_cell_angle_alpha                112.959(2)
_cell_angle_beta                 92.287(2)
_cell_angle_gamma                96.7660(10)
_cell_volume                     1369.67(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11807
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.2050
_cell_measurement_theta_min      3.6220
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.532
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5151
_reflns_number_total             5562
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.090
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_axitinibtranscinnamicacid
_database_code_depnum_ccdc_archive 'CCDC 2080926'
loop_
_audit_author_name
_audit_author_address
'Boying Ren'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N4 O S, C9 H8 O2'
_chemical_formula_sum            'C31 H26 N4 O3 S'
_chemical_formula_weight         534.62
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.85120(10)
_cell_length_b                   13.6163(2)
_cell_length_c                   14.6035(2)
_cell_angle_alpha                62.9890(10)
_cell_angle_beta                 82.2420(10)
_cell_angle_gamma                79.9120(10)
_cell_volume                     1366.64(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10957
_cell_measurement_temperature    275(4)
_cell_measurement_theta_max      79.0600
_cell_measurement_theta_min      5.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18224
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.421
_diffrn_reflns_theta_min         3.748
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      275(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -47.00   0.50    0.50    --    0.00 -53.00  99.00   52
  2  ω    -40.00  26.00   0.50    0.50    --    0.00 -53.00  99.00  132
  3  ω     23.00  71.00   0.50    1.00    --  105.20 -53.00  99.00   96
  4  ω     91.00 130.00   0.50    1.00    --  105.20 -53.00  99.00   78
  5  ω     47.00  89.00   0.50    0.50    --    0.00  57.00 -30.00   84
  6  ω    -88.00  15.00   0.50    0.50    --    0.00 -37.00   0.00  206
  7  ω    -26.00  38.00   0.50    0.50    --    0.00  57.00 -30.00  128
  8  ω      0.00  31.00   0.50    0.50    --    0.00  53.00-115.00   62
  9  ω     16.00  89.00   0.50    1.00    --  105.20 -30.00 -90.00  146
 10  ω     16.00 141.00   0.50    1.00    --  105.20 -82.00 -90.00  250
 11  ω     16.00  63.00   0.50    1.00    --  105.20 -61.00 -90.00   94
 12  ω     64.00 131.00   0.50    1.00    --  105.20 -82.00-120.00  134
 13  ω     27.00 140.00   0.50    1.00    --  105.20 -82.00  90.00  226
 14  ω     17.00 141.00   0.50    1.00    --  105.20 -82.00   0.00  248
 15  ω     20.00  47.00   0.50    1.00    --  105.20 -82.00 150.00   54
 16  ω     70.00 139.00   0.50    1.00    --  105.20 -82.00 150.00  138
 17  ω     99.00 124.00   0.50    1.00    --  105.20  61.00 -30.00   50
 18  ω    166.00 195.00   0.50    1.00    --  105.20  61.00 -30.00   58
 19  ω    140.00 166.00   0.50    1.00    --  105.20  30.00-150.00   52
 20  ω     17.00 136.00   0.50    1.00    --  105.20 -30.00   0.00  238
 21  ω     76.00 132.00   0.50    1.00    --  105.20  30.00-150.00  112
 22  ω     20.00  48.00   0.50    1.00    --  105.20 -82.00-120.00   56
 23  ω    108.00 133.00   0.50    1.00    --  105.20 -61.00 -90.00   50
 24  ω     24.00  70.00   0.50    1.00    --  105.20 -77.00 -60.00   92
 25  ω     21.00  61.00   0.50    1.00    --  105.20  15.00-180.00   80
 26  ω     65.00 194.00   0.50    1.00    --  105.20  15.00-180.00  258
 27  ω     40.00  86.00   0.50    1.00    --  105.20 -77.00  30.00   92
 28  ω     88.00 113.00   0.50    1.00    --  105.20  77.00 -60.00   50
 29  ω    170.00 195.00   0.50    1.00    --  105.20  77.00 -60.00   50
 30  ω     78.00 103.00   0.50    1.00    --  105.20 -82.00 -30.00   50
 31  ω     98.00 123.00   0.50    1.00    --  105.20  53.00-115.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1001782000
_diffrn_orient_matrix_UB_12      -0.0173565000
_diffrn_orient_matrix_UB_13      -0.0741177000
_diffrn_orient_matrix_UB_21      -0.1542422000
_diffrn_orient_matrix_UB_22      0.0816501000
_diffrn_orient_matrix_UB_23      0.0114718000
_diffrn_orient_matrix_UB_31      0.0778090000
_diffrn_orient_matrix_UB_32      0.0971197000
_diffrn_orient_matrix_UB_33      -0.0919337000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5131
_reflns_number_total             5765
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.084
_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)+(0.1065P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1673
_refine_special_details          ?
_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
2. Restrained distances
 O2-H2A
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C11(H11), C14(H14), C7(H7), C16(H16), C6(H6), C13(H13),
 C19(H19), C4(H4A), C25(H25), C17(H17), C27(H27), C1(H1), C18(H18), C3(H3A),
 C2(H2), C24(H24), C28(H28), C31(H31), C29(H29), C30(H30)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.11600(5) 0.33413(4) 0.12112(3) 0.05220(16) Uani 1 1 d . . . . .
O1 O 0.11291(16) 0.20154(11) 0.00372(9) 0.0555(3) Uani 1 1 d . . . . .
O2 O 0.4512(2) 0.25876(11) 0.59801(11) 0.0714(4) Uani 1 1 d D . . . .
N3 N 0.0189(2) 0.68137(11) 0.19442(10) 0.0497(3) Uani 1 1 d . . . . .
H3 H -0.030424 0.730253 0.139834 0.060 Uiso 1 1 calc R U . . .
N4 N 0.2608(2) 0.03831(12) 0.10554(11) 0.0522(3) Uani 1 1 d . . . . .
H4 H 0.350603 0.005448 0.140674 0.063 Uiso 1 1 calc R U . . .
O3 O 0.5112(3) 0.13089(14) 0.75551(12) 0.0850(5) Uani 1 1 d . . . . .
N2 N 0.0485(2) 0.70210(12) 0.27245(10) 0.0508(3) Uani 1 1 d . . . . .
N1 N 0.3645(2) 0.40165(12) 0.67406(10) 0.0523(3) Uani 1 1 d . . . . .
C15 C 0.33580(19) 0.29550(13) 0.08921(10) 0.0424(3) Uani 1 1 d . . . . .
C9 C 0.14792(19) 0.52177(12) 0.30846(10) 0.0400(3) Uani 1 1 d . . . . .
C20 C 0.37712(19) 0.20684(13) 0.06295(11) 0.0433(3) Uani 1 1 d . . . . .
C10 C 0.07583(19) 0.57444(13) 0.21176(11) 0.0414(3) Uani 1 1 d . . . . .
C11 C 0.0696(2) 0.52060(14) 0.15112(11) 0.0445(3) Uani 1 1 d . . . . .
H11 H 0.022262 0.557593 0.087162 0.053 Uiso 1 1 calc R U . . .
C21 C 0.23900(19) 0.14826(13) 0.05527(10) 0.0417(3) Uani 1 1 d . . . . .
C5 C 0.2939(2) 0.50448(14) 0.61026(11) 0.0439(3) Uani 1 1 d . . . . .
C8 C 0.1266(2) 0.60727(13) 0.34237(11) 0.0432(3) Uani 1 1 d . . . . .
C14 C 0.2166(2) 0.40869(14) 0.34603(12) 0.0482(4) Uani 1 1 d . . . . .
H14 H 0.265483 0.371492 0.409516 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1740(2) 0.60443(13) 0.43639(12) 0.0471(4) Uani 1 1 d . . . . .
H7 H 0.152912 0.670224 0.443230 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4684(2) 0.35136(16) 0.08949(13) 0.0530(4) Uani 1 1 d . . . . .
H16 H 0.442341 0.410336 0.106875 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2450(2) 0.51447(14) 0.51277(12) 0.0488(4) Uani 1 1 d . . . . .
H6 H 0.266460 0.450014 0.503639 0.059 Uiso 1 1 calc R U . . .
C12 C 0.1366(2) 0.41035(14) 0.19023(12) 0.0460(4) Uani 1 1 d . . . . .
C13 C 0.2102(2) 0.35446(14) 0.28762(12) 0.0520(4) Uani 1 1 d . . . . .
H13 H 0.254821 0.279716 0.312070 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7104(3) 0.05040(16) 0.46475(16) 0.0608(5) Uani 1 1 d . . . . .
C19 C 0.5492(2) 0.17652(17) 0.03819(14) 0.0569(4) Uani 1 1 d . . . . .
H19 H 0.576919 0.117317 0.021178 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2706(2) 0.59057(15) 0.63866(13) 0.0519(4) Uani 1 1 d . . . . .
H4A H 0.222409 0.661472 0.594278 0.062 Uiso 1 1 calc R U . . .
C25 C 0.6202(3) 0.11704(16) 0.51639(16) 0.0601(5) Uani 1 1 d . . . . .
H25 H 0.563181 0.186257 0.474591 0.072 Uiso 1 1 calc R U . . .
C23 C 0.5198(3) 0.16088(16) 0.66288(16) 0.0643(5) Uani 1 1 d . . . . .
C17 C 0.6381(2) 0.3199(2) 0.06417(14) 0.0625(5) Uani 1 1 d . . . . .
H17 H 0.725242 0.357970 0.064522 0.075 Uiso 1 1 calc R U . . .
C27 C 0.8031(3) -0.05340(17) 0.51705(17) 0.0696(6) Uani 1 1 d . . . . .
H27 H 0.810978 -0.082357 0.587785 0.083 Uiso 1 1 calc R U . . .
C1 C 0.4108(3) 0.38347(18) 0.76540(14) 0.0619(5) Uani 1 1 d . . . . .
H1 H 0.459213 0.312229 0.808824 0.074 Uiso 1 1 calc R U . . .
C18 C 0.6795(2) 0.2325(2) 0.03835(16) 0.0675(5) Uani 1 1 d . . . . .
H18 H 0.793871 0.211534 0.021261 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3201(3) 0.56929(19) 0.73412(15) 0.0620(5) Uani 1 1 d . . . . .
H3A H 0.305583 0.625921 0.754509 0.074 Uiso 1 1 calc R U . . .
C2 C 0.3909(3) 0.4637(2) 0.79858(14) 0.0648(5) Uani 1 1 d . . . . .
H2 H 0.424251 0.447604 0.863157 0.078 Uiso 1 1 calc R U . . .
C22 C 0.1379(3) -0.02823(19) 0.10311(19) 0.0694(5) Uani 1 1 d . . . . .
H22A H 0.142956 -0.024039 0.035398 0.104 Uiso 1 1 calc R U . . .
H22B H 0.023049 -0.000600 0.120114 0.104 Uiso 1 1 calc R U . . .
H22C H 0.166181 -0.104158 0.152219 0.104 Uiso 1 1 calc R U . . .
C24 C 0.6113(3) 0.08944(18) 0.61575(17) 0.0710(6) Uani 1 1 d . . . . .
H24 H 0.666476 0.020196 0.658938 0.085 Uiso 1 1 calc R U . . .
C28 C 0.8838(3) -0.1143(2) 0.4661(2) 0.0795(7) Uani 1 1 d . . . . .
H28 H 0.945269 -0.183819 0.502872 0.095 Uiso 1 1 calc R U . . .
C31 C 0.7027(4) 0.0908(2) 0.35948(19) 0.0858(8) Uani 1 1 d . . . . .
H31 H 0.641186 0.160132 0.322258 0.103 Uiso 1 1 calc R U . . .
C29 C 0.8750(4) -0.0742(2) 0.3621(2) 0.0890(8) Uani 1 1 d . . . . .
H29 H 0.928368 -0.115918 0.327998 0.107 Uiso 1 1 calc R U . . .
C30 C 0.7852(5) 0.0293(3) 0.3093(2) 0.1033(10) Uani 1 1 d . . . . .
H30 H 0.780201 0.058406 0.238334 0.124 Uiso 1 1 calc R U . . .
H2A H 0.420(5) 0.296(3) 0.633(2) 0.115(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.7774(15) . ?
S1 C12 1.7821(17) . ?
O1 C21 1.2355(18) . ?
O2 C23 1.305(2) . ?
O2 H2A 0.864(18) . ?
N3 H3 0.8600 . ?
N3 N2 1.348(2) . ?
N3 C10 1.361(2) . ?
N4 H4 0.8600 . ?
N4 C21 1.325(2) . ?
N4 C22 1.448(3) . ?
O3 C23 1.218(3) . ?
N2 C8 1.3343(19) . ?
N1 C5 1.349(2) . ?
N1 C1 1.331(2) . ?
C15 C20 1.400(2) . ?
C15 C16 1.394(2) . ?
C9 C10 1.4081(19) . ?
C9 C8 1.436(2) . ?
C9 C14 1.409(2) . ?
C20 C21 1.497(2) . ?
C20 C19 1.391(2) . ?
C10 C11 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(2) . ?
C5 C6 1.465(2) . ?
C5 C4 1.388(2) . ?
C8 C7 1.452(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.368(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.320(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.422(2) . ?
C13 H13 0.9300 . ?
C26 C25 1.465(3) . ?
C26 C27 1.386(3) . ?
C26 C31 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.379(3) . ?
C4 H4A 0.9300 . ?
C4 C3 1.385(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.318(3) . ?
C23 C24 1.472(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.362(3) . ?
C18 H18 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C2 1.376(3) . ?
C2 H2 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.367(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(4) . ?
C30 H30 0.9300 . ?

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
C15 S1 C12 102.30(8) . . ?
C23 O2 H2A 106(2) . . ?
N2 N3 H3 123.8 . . ?
N2 N3 C10 112.43(12) . . ?
C10 N3 H3 123.8 . . ?
C21 N4 H4 119.0 . . ?
C21 N4 C22 122.00(15) . . ?
C22 N4 H4 119.0 . . ?
C8 N2 N3 106.42(13) . . ?
C1 N1 C5 119.00(16) . . ?
C20 C15 S1 119.26(12) . . ?
C16 C15 S1 121.70(13) . . ?
C16 C15 C20 119.04(15) . . ?
C10 C9 C8 104.25(13) . . ?
C10 C9 C14 118.37(14) . . ?
C14 C9 C8 137.39(13) . . ?
C15 C20 C21 121.33(13) . . ?
C19 C20 C15 119.23(16) . . ?
C19 C20 C21 119.36(15) . . ?
N3 C10 C9 106.45(14) . . ?
N3 C10 C11 130.20(14) . . ?
C11 C10 C9 123.35(14) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.80(13) . . ?
C12 C11 H11 121.6 . . ?
O1 C21 N4 122.86(16) . . ?
O1 C21 C20 120.57(14) . . ?
N4 C21 C20 116.57(13) . . ?
N1 C5 C6 114.34(15) . . ?
N1 C5 C4 120.77(15) . . ?
C4 C5 C6 124.88(15) . . ?
N2 C8 C9 110.46(13) . . ?
N2 C8 C7 118.81(15) . . ?
C9 C8 C7 130.73(14) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 C9 118.94(14) . . ?
C13 C14 H14 120.5 . . ?
C8 C7 H7 117.9 . . ?
C6 C7 C8 124.23(15) . . ?
C6 C7 H7 117.9 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.58(18) . . ?
C17 C16 H16 119.7 . . ?
C5 C6 H6 116.3 . . ?
C7 C6 C5 127.49(16) . . ?
C7 C6 H6 116.3 . . ?
C11 C12 S1 118.81(12) . . ?
C11 C12 C13 121.37(15) . . ?
C13 C12 S1 119.67(13) . . ?
C14 C13 C12 121.17(15) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C27 C26 C25 122.79(19) . . ?
C31 C26 C25 119.55(19) . . ?
C31 C26 C27 117.7(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.34(19) . . ?
C18 C19 H19 119.3 . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 C5 118.98(18) . . ?
C3 C4 H4A 120.5 . . ?
C26 C25 H25 116.5 . . ?
C24 C25 C26 126.99(18) . . ?
C24 C25 H25 116.5 . . ?
O2 C23 C24 115.00(18) . . ?
O3 C23 O2 122.82(19) . . ?
O3 C23 C24 122.18(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 H27 119.4 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.43(19) . . ?
C2 C1 H1 118.3 . . ?
C19 C18 C17 119.22(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 C4 119.51(19) . . ?
C2 C3 H3A 120.2 . . ?
C1 C2 C3 118.31(17) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
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 . . ?
C25 C24 C23 124.37(18) . . ?
C25 C24 H24 117.8 . . ?
C23 C24 H24 117.8 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.9(2) . . ?
C29 C28 H28 119.5 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C28 C29 H29 120.8 . . ?
C28 C29 C30 118.4(2) . . ?
C30 C29 H29 120.8 . . ?
C31 C30 H30 119.4 . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?

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
N3 H3 O1 0.86 2.02 2.8329(17) 158.3 2_565
N4 H4 O3 0.86 2.03 2.814(2) 152.0 2_656
O2 H2A N1 0.864(18) 1.76(2) 2.603(2) 166(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 C20 C21 3.59(19) . . . . ?
S1 C15 C20 C19 -179.87(12) . . . . ?
S1 C15 C16 C17 -179.85(13) . . . . ?
S1 C12 C13 C14 -175.27(14) . . . . ?
O2 C23 C24 C25 -2.8(4) . . . . ?
N3 N2 C8 C9 -0.20(19) . . . . ?
N3 N2 C8 C7 -179.69(15) . . . . ?
N3 C10 C11 C12 -179.21(16) . . . . ?
O3 C23 C24 C25 178.1(3) . . . . ?
N2 N3 C10 C9 -0.01(19) . . . . ?
N2 N3 C10 C11 179.89(16) . . . . ?
N2 C8 C7 C6 177.05(17) . . . . ?
N1 C5 C6 C7 -179.92(18) . . . . ?
N1 C5 C4 C3 -0.4(3) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
C15 S1 C12 C11 117.37(14) . . . . ?
C15 S1 C12 C13 -67.11(15) . . . . ?
C15 C20 C21 O1 50.4(2) . . . . ?
C15 C20 C21 N4 -129.98(15) . . . . ?
C15 C20 C19 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C8 C7 C6 -2.3(3) . . . . ?
C9 C14 C13 C12 0.3(3) . . . . ?
C20 C15 C16 C17 0.1(2) . . . . ?
C20 C19 C18 C17 0.4(3) . . . . ?
C10 N3 N2 C8 0.1(2) . . . . ?
C10 C9 C8 N2 0.19(18) . . . . ?
C10 C9 C8 C7 179.61(16) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C10 C11 C12 S1 174.85(12) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C21 C20 C19 C18 176.17(16) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C8 C9 C10 N3 -0.10(17) . . . . ?
C8 C9 C10 C11 179.99(14) . . . . ?
C8 C9 C14 C13 179.41(19) . . . . ?
C8 C7 C6 C5 -179.01(16) . . . . ?
C14 C9 C10 N3 179.63(14) . . . . ?
C14 C9 C10 C11 -0.3(2) . . . . ?
C14 C9 C8 N2 -179.46(19) . . . . ?
C14 C9 C8 C7 0.0(3) . . . . ?
C16 C15 C20 C21 -176.31(13) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C6 C5 C4 C3 178.91(17) . . . . ?
C12 S1 C15 C20 160.26(12) . . . . ?
C12 S1 C15 C16 -19.84(15) . . . . ?
C26 C25 C24 C23 179.3(2) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C26 C31 C30 C29 1.0(6) . . . . ?
C19 C20 C21 O1 -126.10(17) . . . . ?
C19 C20 C21 N4 53.5(2) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?
C25 C26 C27 C28 178.9(2) . . . . ?
C25 C26 C31 C30 -179.5(3) . . . . ?
C27 C26 C25 C24 -1.1(4) . . . . ?
C27 C26 C31 C30 -0.2(4) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C1 N1 C5 C6 -178.92(17) . . . . ?
C1 N1 C5 C4 0.4(3) . . . . ?
C22 N4 C21 O1 0.5(3) . . . . ?
C22 N4 C21 C20 -179.10(16) . . . . ?
C28 C29 C30 C31 -1.4(6) . . . . ?
C31 C26 C25 C24 178.2(3) . . . . ?
C31 C26 C27 C28 -0.4(4) . . . . ?

_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 3.438
_oxdiff_exptl_absorpt_empirical_full_min 0.363
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_axitinib_fumaricacid
_database_code_depnum_ccdc_archive 'CCDC 2022625'
loop_
_audit_author_name
_audit_author_address
'Boying Ren'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_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
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1582(3)
_cell_length_b                   13.1348(4)
_cell_length_c                   13.1911(4)
_cell_angle_alpha                102.579(3)
_cell_angle_beta                 105.605(3)
_cell_angle_gamma                93.678(3)
_cell_volume                     1317.35(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10693
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.8570
_cell_measurement_theta_min      3.4630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4972
_reflns_number_total             5560
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.074
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
