# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_rby0526
_database_code_depnum_ccdc_archive 'CCDC 2022622'
loop_
_audit_author_name
_audit_author_address
'Boying Ren'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2021-11-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_audit_creation_date             2021-11-28
_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, C5 H7.997 O4, H2 O'
_chemical_formula_sum            'C27 H28 N4 O6 S'
_chemical_formula_weight         536.59
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.1885(2)
_cell_length_b                   7.66640(10)
_cell_length_c                   22.5682(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8180(10)
_cell_angle_gamma                90
_cell_volume                     2627.60(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.7360
_cell_measurement_theta_min      3.8910
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58093
_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            white
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       flake
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15717
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.485
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  22.00   0.50    0.69    --    0.00 -57.00  60.00  104
  2  ω    -87.00  27.00   0.50    0.69    --    0.00 -57.00 -30.00  228
  3  ω    -81.00 -56.00   0.50    0.69    --    0.00 -57.00 -60.00   50
  4  ω    -81.00 -41.00   0.50    0.69    --    0.00 -57.00  60.00   80
  5  ω    -19.00   6.00   0.50    0.69    --    0.00 -57.00 -60.00   50
  6  ω     21.00 140.00   0.50    4.00    --  106.20 -30.00 150.00  238
  7  ω     52.00 112.00   0.50    4.00    --  106.20 -77.00 -30.00  120
  8  ω    169.00 195.00   0.50    4.00    --  106.20 -15.00 -30.00   52
  9  ω     75.00 110.00   0.50    4.00    --  106.20 -82.00  30.00   70
 10  ω     37.00  66.00   0.50    4.00    --  106.20 -82.00  30.00   58
 11  ω     99.00 125.00   0.50    4.00    --  106.20 -61.00-150.00   52
 12  ω     34.00 133.00   0.50    4.00    --  106.20 -30.00  30.00  198
 13  ω     17.00 134.00   0.50    4.00    --  106.20 -45.00 -60.00  234
 14  ω     35.00 138.00   0.50    4.00    --  106.20 -77.00  60.00  206
 15  ω    103.00 149.00   0.50    4.00    --  106.20 -15.00 -30.00   92
 16  ω     33.00  84.00   0.50    4.00    --  106.20 -15.00 -30.00  102
;
_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      -0.0755688000
_diffrn_orient_matrix_UB_12      -0.0210599000
_diffrn_orient_matrix_UB_13      -0.0457452000
_diffrn_orient_matrix_UB_21      0.0675932000
_diffrn_orient_matrix_UB_22      -0.0305916000
_diffrn_orient_matrix_UB_23      -0.0491263000
_diffrn_orient_matrix_UB_31      -0.0024605000
_diffrn_orient_matrix_UB_32      -0.1975007000
_diffrn_orient_matrix_UB_33      0.0125018000
_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                4096
_reflns_number_total             4696
_reflns_odcompleteness_completeness 99.86
_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    ?
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4696
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.071
_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)+(0.0759P)²+2.2471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1524
_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, All O(H,H) groups
2. Restrained distances
 C30-C29
 1.54 with sigma of 0.02
 H6A-O6
 0.82 with sigma of 0.01
 C31-O8
 1.2 with sigma of 0.02
 O9-C31
 1.28 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C30)
Uanis(C24) = Uanis(C32)
Uanis(C27) = Uanis(C31)
Uanis(C26) = Uanis(C29)
Uanis(O4) = Uanis(O8)
Uanis(O2) = Uanis(O11)
Uanis(O5) = Uanis(O7)
Uanis(C23) = Uanis(C342)
Uanis(O6) = Uanis(O10)
Uanis(O3) = Uanis(O9)
4. Others
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(C32)=
 Sof(H32A)=Sof(H32B)=Sof(C342)=Sof(O10)=Sof(H10)=Sof(O7)=Sof(O8)=Sof(O9)=
 Sof(H9)=1-FVAR(1)
 Sof(C23)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(O6)=Sof(O3)=Sof(H3B)=Sof(O5)=Sof(O4)=FVAR(1)
 Sof(O11)=Sof(H11A)=Sof(H11B)=1-FVAR(2)
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(2)
 Fixed Sof: H6A(0.78)
5.a Riding coordinates:
 O3(H3B), O9(H9)
5.b Free rotating group:
 O2(H2A,H2B), O11(H11A,H11B)
5.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C29(H29A,H29B), C30(H30A,
 H30B), C32(H32A,H32B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), N4(H4A), N3(H3A)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
5.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
;
_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
C1 C 0.71706(16) 0.5715(4) 0.57952(13) 0.0414(6) Uani 1 1 d . . . . .
H1 H 0.736719 0.526230 0.615574 0.050 Uiso 1 1 calc R U . . .
C2 C 0.77703(17) 0.5924(4) 0.53526(12) 0.0378(6) Uani 1 1 d . . . . .
H2 H 0.835841 0.562112 0.540905 0.045 Uiso 1 1 calc R U . . .
C3 C 0.74699(16) 0.6601(3) 0.48199(12) 0.0353(6) Uani 1 1 d . . . . .
H3 H 0.785724 0.676158 0.450909 0.042 Uiso 1 1 calc R U . . .
C4 C 0.65922(16) 0.7040(3) 0.47501(11) 0.0338(6) Uani 1 1 d . . . . .
H4 H 0.638609 0.750253 0.439323 0.041 Uiso 1 1 calc R U . . .
C5 C 0.60205(15) 0.6786(3) 0.52165(11) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.50840(15) 0.7203(3) 0.51856(11) 0.0320(5) Uani 1 1 d . . . . .
H6 H 0.474632 0.694701 0.551499 0.038 Uiso 1 1 calc R U . . .
C7 C 0.46777(15) 0.7923(3) 0.47197(11) 0.0309(5) Uani 1 1 d . . . . .
H7 H 0.501927 0.813130 0.438829 0.037 Uiso 1 1 calc R U . . .
C8 C 0.37557(15) 0.8417(3) 0.46759(10) 0.0269(5) Uani 1 1 d . . . . .
C9 C 0.30435(14) 0.8273(3) 0.50849(10) 0.0235(5) Uani 1 1 d . . . . .
C10 C 0.23137(15) 0.8989(3) 0.47816(10) 0.0246(5) Uani 1 1 d . . . . .
C11 C 0.14733(14) 0.9088(3) 0.50236(10) 0.0247(5) Uani 1 1 d . . . . .
H11 H 0.100106 0.956882 0.481372 0.030 Uiso 1 1 calc R U . . .
C12 C 0.13788(14) 0.8439(3) 0.55875(10) 0.0238(5) Uani 1 1 d . . . . .
C13 C 0.20993(15) 0.7701(3) 0.59051(10) 0.0268(5) Uani 1 1 d . . . . .
H13 H 0.201430 0.727374 0.628566 0.032 Uiso 1 1 calc R U . . .
C14 C 0.29197(14) 0.7607(3) 0.56609(10) 0.0272(5) Uani 1 1 d . . . . .
H14 H 0.338731 0.711208 0.587154 0.033 Uiso 1 1 calc R U . . .
C15 C 0.00284(13) 0.6483(3) 0.60596(9) 0.0207(4) Uani 1 1 d . . . . .
C16 C 0.04052(14) 0.5115(3) 0.57452(10) 0.0261(5) Uani 1 1 d . . . . .
H16 H 0.082131 0.535161 0.545781 0.031 Uiso 1 1 calc R U . . .
C17 C 0.01641(16) 0.3401(3) 0.58580(11) 0.0309(5) Uani 1 1 d . . . . .
H17 H 0.041607 0.250244 0.564175 0.037 Uiso 1 1 calc R U . . .
C18 C -0.04449(14) 0.3015(3) 0.62869(11) 0.0291(5) Uani 1 1 d . . . . .
H18 H -0.059588 0.186383 0.636660 0.035 Uiso 1 1 calc R U . . .
C19 C -0.08283(14) 0.4376(3) 0.65975(10) 0.0257(5) Uani 1 1 d . . . . .
H19 H -0.123921 0.412561 0.688700 0.031 Uiso 1 1 calc R U . . .
C20 C -0.06097(13) 0.6108(3) 0.64842(9) 0.0211(4) Uani 1 1 d . . . . .
C21 C -0.11256(13) 0.7539(3) 0.67719(10) 0.0241(5) Uani 1 1 d . . . . .
C22 C -0.1955(2) 0.8462(4) 0.76292(15) 0.0558(9) Uani 1 1 d . . . . .
H22A H -0.249353 0.854877 0.740343 0.084 Uiso 1 1 calc R U . . .
H22B H -0.168944 0.959444 0.766327 0.084 Uiso 1 1 calc R U . . .
H22C H -0.207782 0.801954 0.801730 0.084 Uiso 1 1 calc R U . . .
N4 N -0.13531(15) 0.7281(3) 0.73310(9) 0.0377(5) Uani 1 1 d . . . . .
H4A H -0.114125 0.640006 0.752104 0.045 Uiso 1 1 calc R U . . .
N2 N 0.34691(13) 0.9165(3) 0.41745(9) 0.0305(4) Uani 1 1 d . . . . .
N1 N 0.63169(14) 0.6127(3) 0.57365(10) 0.0389(5) Uani 1 1 d . . . . .
N3 N 0.26009(13) 0.9500(3) 0.42391(9) 0.0295(4) Uani 1 1 d . . . . .
H3A H 0.227166 0.997587 0.397132 0.035 Uiso 1 1 calc R U . . .
O1 O -0.13527(11) 0.8846(2) 0.64855(8) 0.0323(4) Uani 1 1 d . . . . .
S1 S 0.03340(3) 0.86820(7) 0.59250(3) 0.02627(18) Uani 1 1 d . . . . .
C23 C 0.4726(3) 0.5503(6) 0.6797(2) 0.0430(10) Uani 0.783(2) 1 d . . P A 1
C24 C 0.4247(4) 0.5782(9) 0.7359(3) 0.0547(14) Uani 0.783(2) 1 d . . P A 1
H24A H 0.437459 0.481135 0.762205 0.066 Uiso 0.783(2) 1 calc R U P A 1
H24B H 0.447579 0.682903 0.754697 0.066 Uiso 0.783(2) 1 calc R U P A 1
C25 C 0.3281(3) 0.5956(6) 0.72995(17) 0.0517(9) Uani 0.783(2) 1 d . . P A 1
H25A H 0.306076 0.497169 0.707165 0.062 Uiso 0.783(2) 1 calc R U P A 1
H25B H 0.315382 0.700242 0.707247 0.062 Uiso 0.783(2) 1 calc R U P A 1
C26 C 0.2768(4) 0.6048(7) 0.78818(19) 0.0558(11) Uani 0.783(2) 1 d . . P A 1
H26A H 0.293653 0.506645 0.812950 0.067 Uiso 0.783(2) 1 calc R U P A 1
H26B H 0.293294 0.710676 0.809095 0.067 Uiso 0.783(2) 1 calc R U P A 1
C27 C 0.1792(3) 0.6029(6) 0.77928(18) 0.0538(10) Uani 0.783(2) 1 d . . P A 1
O6 O 0.5473(2) 0.6350(5) 0.67393(15) 0.0540(7) Uani 0.783(2) 1 d D . P A 1
H6A H 0.566(5) 0.618(10) 0.6402(15) 0.14(3) Uiso 0.78 1 d D . P B 1
O3 O 0.1342(2) 0.5778(5) 0.82941(14) 0.0660(9) Uani 0.783(2) 1 d . . P A 1
H3B H 0.082884 0.553409 0.821135 0.099 Uiso 0.783(2) 1 d R U P A 1
O5 O 0.4427(2) 0.4614(5) 0.64072(14) 0.0722(9) Uani 0.783(2) 1 d . . P A 1
O4 O 0.1429(2) 0.6206(7) 0.73258(14) 0.0942(14) Uani 0.783(2) 1 d . . P A 1
O2 O -0.04486(19) 0.5111(4) 0.81882(12) 0.0435(6) Uani 0.714(4) 1 d G . P C 1
H2A H -0.041271 0.400808 0.816218 0.065 Uiso 0.714(4) 1 d G U P C 1
H2B H -0.076341 0.528638 0.849078 0.065 Uiso 0.714(4) 1 d G U P C 1
C29 C 0.3248(11) 0.679(2) 0.8007(6) 0.0558(11) Uani 0.217(2) 1 d D . P A 2
H29A H 0.343130 0.578889 0.824157 0.067 Uiso 0.217(2) 1 calc R U P A 2
H29B H 0.328696 0.780958 0.826031 0.067 Uiso 0.217(2) 1 calc R U P A 2
C30 C 0.3881(10) 0.701(2) 0.7503(6) 0.0517(9) Uani 0.217(2) 1 d D . P A 2
H30A H 0.428620 0.795750 0.759017 0.062 Uiso 0.217(2) 1 calc R U P A 2
H30B H 0.355865 0.729543 0.714151 0.062 Uiso 0.217(2) 1 calc R U P A 2
C31 C 0.2328(13) 0.655(3) 0.7823(6) 0.0538(10) Uani 0.217(2) 1 d D . P A 2
C32 C 0.440(2) 0.529(4) 0.7418(14) 0.0547(14) Uani 0.217(2) 1 d . . P A 2
H32A H 0.472720 0.498961 0.777655 0.066 Uiso 0.217(2) 1 calc R U P A 2
H32B H 0.400385 0.433601 0.732023 0.066 Uiso 0.217(2) 1 calc R U P A 2
C342 C 0.5024(13) 0.563(3) 0.6912(10) 0.0430(10) Uani 0.217(2) 1 d . . P A 2
O10 O 0.5103(7) 0.4678(16) 0.6431(4) 0.0540(7) Uani 0.217(2) 1 d . . P A 2
H10 H 0.547368 0.511498 0.621602 0.081 Uiso 0.217(2) 1 calc R U P A 2
O7 O 0.5606(9) 0.6728(19) 0.7068(6) 0.0722(9) Uani 0.217(2) 1 d . . P A 2
O8 O 0.2131(9) 0.609(2) 0.7315(5) 0.0942(14) Uani 0.217(2) 1 d D . P A 2
O9 O 0.1797(9) 0.6332(19) 0.8256(6) 0.0660(9) Uani 0.217(2) 1 d D . P A 2
H9 H 0.126957 0.613907 0.815594 0.099 Uiso 0.217(2) 1 d R U P A 2
O11 O -0.1115(5) 0.4479(10) 0.8072(3) 0.0435(6) Uani 0.286(4) 1 d G . P C 2
H11A H -0.101714 0.339402 0.811530 0.065 Uiso 0.286(4) 1 d G U P C 2
H11B H -0.118722 0.485841 0.842191 0.065 Uiso 0.286(4) 1 d G U P C 2


_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
C1 H1 0.9300 . ?
C1 C2 1.371(4) . ?
C1 N1 1.339(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 C6 1.459(3) . ?
C5 N1 1.349(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.331(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.453(3) . ?
C8 C9 1.436(3) . ?
C8 N2 1.336(3) . ?
C9 C10 1.406(3) . ?
C9 C14 1.411(3) . ?
C10 C11 1.398(3) . ?
C10 N3 1.363(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 C13 1.417(3) . ?
C12 S1 1.780(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(3) . ?
C15 C20 1.403(3) . ?
C15 S1 1.776(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(3) . ?
C20 C21 1.501(3) . ?
C21 N4 1.328(3) . ?
C21 O1 1.239(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 N4 1.458(3) . ?
N4 H4A 0.8600 . ?
N2 N3 1.353(3) . ?
N3 H3A 0.8600 . ?
C23 C24 1.488(9) . ?
C23 O6 1.315(6) . ?
C23 O5 1.196(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.476(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.539(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.493(7) . ?
C27 O3 1.344(5) . ?
C27 O4 1.190(5) . ?
O6 H6A 0.827(10) . ?
O3 H3B 0.8202 . ?
O2 H2A 0.8495 . ?
O2 H2B 0.8498 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.510(15) . ?
C29 C31 1.46(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C32 1.55(3) . ?
C31 O8 1.231(15) . ?
C31 O9 1.287(15) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C342 1.52(4) . ?
C342 O10 1.32(3) . ?
C342 O7 1.27(2) . ?
O10 H10 0.8200 . ?
O9 H9 0.8429 . ?
O11 H11A 0.8505 . ?
O11 H11B 0.8503 . ?

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
C2 C1 H1 118.2 . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(3) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.6(2) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 123.6(2) . . ?
N1 C5 C4 120.5(2) . . ?
N1 C5 C6 115.9(2) . . ?
C5 C6 H6 117.7 . . ?
C7 C6 C5 124.7(2) . . ?
C7 C6 H6 117.7 . . ?
C6 C7 H7 116.7 . . ?
C6 C7 C8 126.7(2) . . ?
C8 C7 H7 116.7 . . ?
C9 C8 C7 132.1(2) . . ?
N2 C8 C7 118.1(2) . . ?
N2 C8 C9 109.77(19) . . ?
C10 C9 C8 104.6(2) . . ?
C10 C9 C14 118.4(2) . . ?
C14 C9 C8 137.0(2) . . ?
C11 C10 C9 123.3(2) . . ?
N3 C10 C9 106.8(2) . . ?
N3 C10 C11 129.9(2) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.7(2) . . ?
C12 C11 H11 121.6 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 S1 117.61(17) . . ?
C13 C12 S1 120.80(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 120.5 . . ?
C13 C14 C9 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C20 119.1(2) . . ?
C16 C15 S1 121.14(17) . . ?
C20 C15 S1 119.78(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C21 121.04(19) . . ?
C19 C20 C15 119.3(2) . . ?
C19 C20 C21 119.33(19) . . ?
N4 C21 C20 116.5(2) . . ?
O1 C21 C20 120.6(2) . . ?
O1 C21 N4 122.8(2) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
C21 N4 C22 121.3(2) . . ?
C21 N4 H4A 119.3 . . ?
C22 N4 H4A 119.3 . . ?
C8 N2 N3 107.25(19) . . ?
C1 N1 C5 119.0(2) . . ?
C10 N3 H3A 124.2 . . ?
N2 N3 C10 111.52(18) . . ?
N2 N3 H3A 124.2 . . ?
C15 S1 C12 102.17(10) . . ?
O6 C23 C24 116.5(5) . . ?
O5 C23 C24 121.5(5) . . ?
O5 C23 O6 121.9(5) . . ?
C23 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
C25 C24 C23 115.6(5) . . ?
C25 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
C24 C25 H25A 108.2 . . ?
C24 C25 H25B 108.2 . . ?
C24 C25 C26 116.2(4) . . ?
H25A C25 H25B 107.4 . . ?
C26 C25 H25A 108.2 . . ?
C26 C25 H25B 108.2 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 C25 113.5(4) . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
O3 C27 C26 113.8(4) . . ?
O4 C27 C26 124.3(4) . . ?
O4 C27 O3 121.9(4) . . ?
C23 O6 H6A 109(6) . . ?
C27 O3 H3B 109.5 . . ?
H2A O2 H2B 104.5 . . ?
H29A C29 H29B 107.6 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C31 C29 H29A 108.6 . . ?
C31 C29 H29B 108.6 . . ?
C31 C29 C30 114.6(13) . . ?
C29 C30 H30A 109.9 . . ?
C29 C30 H30B 109.9 . . ?
C29 C30 C32 109.1(16) . . ?
H30A C30 H30B 108.3 . . ?
C32 C30 H30A 109.9 . . ?
C32 C30 H30B 109.9 . . ?
O8 C31 C29 121.2(15) . . ?
O8 C31 O9 121.6(18) . . ?
O9 C31 C29 114.0(14) . . ?
C30 C32 H32A 110.6 . . ?
C30 C32 H32B 110.6 . . ?
H32A C32 H32B 108.7 . . ?
C342 C32 C30 105.7(18) . . ?
C342 C32 H32A 110.6 . . ?
C342 C32 H32B 110.6 . . ?
O10 C342 C32 126(2) . . ?
O7 C342 C32 110(2) . . ?
O7 C342 O10 122(2) . . ?
C342 O10 H10 109.5 . . ?
C31 O9 H9 115.0 . . ?
H11A O11 H11B 104.6 . . ?

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 H4A O2 0.86 2.07 2.885(3) 156.6 .
N4 H4A O11 0.86 1.93 2.743(7) 157.8 .
N3 H3A O1 0.86 1.95 2.791(2) 167.1 3_576
O6 H6A N1 0.827(10) 1.81(2) 2.623(4) 165(8) .
O3 H3B O2 0.82 1.97 2.774(5) 167.7 .
O2 H2A O6 0.85 2.05 2.888(5) 168.0 2_546
O2 H2B N2 0.85 1.99 2.841(3) 176.3 4_576
O10 H10 N1 0.82 1.86 2.678(11) 179.3 .
O11 H11A O7 0.85 1.48 2.270(16) 152.1 2_546
O11 H11B N2 0.85 1.93 2.778(7) 171.1 4_576

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
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C1 N1 C5 0.0(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C4 C5 C6 C7 -2.4(4) . . . . ?
C4 C5 N1 C1 -0.2(4) . . . . ?
C5 C6 C7 C8 -177.7(2) . . . . ?
C6 C5 N1 C1 180.0(2) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C6 C7 C8 N2 178.5(3) . . . . ?
C7 C8 C9 C10 179.8(2) . . . . ?
C7 C8 C9 C14 -1.7(5) . . . . ?
C7 C8 N2 N3 180.0(2) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C10 N3 0.0(2) . . . . ?
C8 C9 C14 C13 -179.1(3) . . . . ?
C8 N2 N3 C10 0.4(3) . . . . ?
C9 C8 N2 N3 -0.4(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C10 N3 N2 -0.2(3) . . . . ?
C10 C9 C14 C13 -0.8(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 S1 175.87(16) . . . . ?
C11 C10 N3 N2 -179.6(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C11 C12 S1 C15 120.12(18) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C13 C12 S1 C15 -63.7(2) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C14 C9 C10 N3 -178.9(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C15 C20 C21 N4 -146.8(2) . . . . ?
C15 C20 C21 O1 36.3(3) . . . . ?
C16 C15 C20 C19 2.4(3) . . . . ?
C16 C15 C20 C21 -171.28(19) . . . . ?
C16 C15 S1 C12 -21.1(2) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 -1.8(3) . . . . ?
C18 C19 C20 C21 171.9(2) . . . . ?
C19 C20 C21 N4 39.6(3) . . . . ?
C19 C20 C21 O1 -137.4(2) . . . . ?
C20 C15 C16 C17 -1.1(3) . . . . ?
C20 C15 S1 C12 159.61(16) . . . . ?
C20 C21 N4 C22 -171.4(2) . . . . ?
N2 C8 C9 C10 0.3(3) . . . . ?
N2 C8 C9 C14 178.8(3) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
N1 C5 C6 C7 177.3(3) . . . . ?
N3 C10 C11 C12 179.2(2) . . . . ?
O1 C21 N4 C22 5.5(4) . . . . ?
S1 C12 C13 C14 -175.99(18) . . . . ?
S1 C15 C16 C17 179.57(18) . . . . ?
S1 C15 C20 C19 -178.34(16) . . . . ?
S1 C15 C20 C21 8.0(3) . . . . ?
C23 C24 C25 C26 173.7(4) . . . . ?
C24 C25 C26 C27 -173.8(5) . . . . ?
C25 C26 C27 O3 168.1(4) . . . . ?
C25 C26 C27 O4 -11.5(7) . . . . ?
O6 C23 C24 C25 139.1(5) . . . . ?
O5 C23 C24 C25 -37.6(7) . . . . ?
C29 C30 C32 C342 -179.3(17) . . . . ?
C30 C29 C31 O8 19(3) . . . . ?
C30 C29 C31 O9 179.0(16) . . . . ?
C30 C32 C342 O10 -127(2) . . . . ?
C30 C32 C342 O7 68(2) . . . . ?
C31 C29 C30 C32 -104(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 1.909
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_axi-ga
_database_code_depnum_ccdc_archive 'CCDC 2045671'
loop_
_audit_author_name
_audit_author_address
'Boying Ren'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2021-11-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_audit_creation_date             2021-11-28
_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, C5 H8 O4'
_chemical_formula_sum            'C27 H26 N4 O5 S'
_chemical_formula_weight         518.58
_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                   7.6975(2)
_cell_length_b                   12.7075(3)
_cell_length_c                   14.7757(4)
_cell_angle_alpha                65.633(3)
_cell_angle_beta                 83.024(2)
_cell_angle_gamma                77.802(2)
_cell_volume                     1285.88(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10522
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.1230
_cell_measurement_theta_min      3.2670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14648
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.314
_diffrn_reflns_theta_min         3.286
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4971
_reflns_number_total             5413
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.325
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5413
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.078
_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)+(0.1109P)²+0.4355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1677
_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. Restrained distances
 O5-H5
 0.84 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C24(H24A,H24B), C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C16(H16), C7(H7), C11(H11), C19(H19), C14(H14), C4(H4A),
 C18(H18), C17(H17), C6(H6), C1(H1), C13(H13), C3(H3A), C2(H2)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_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 0.08744(5) 0.32123(4) 0.12266(3) 0.02782(16) Uani 1 1 d . . . . .
O1 O 0.11224(17) 0.17933(12) -0.01044(10) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.4315(2) 0.23809(12) 0.59467(10) 0.0392(4) Uani 1 1 d . . . . .
H2A H 0.425799 0.286315 0.618950 0.059 Uiso 1 1 calc R U . . .
O3 O 0.4736(3) 0.11310(13) 0.75132(12) 0.0467(4) Uani 1 1 d . . . . .
N2 N 0.0057(2) 0.71245(13) 0.28596(11) 0.0261(3) Uani 1 1 d . . . . .
N3 N -0.0269(2) 0.68949(13) 0.20878(11) 0.0260(3) Uani 1 1 d . . . . .
H3 H -0.080543 0.741072 0.156671 0.031 Uiso 1 1 calc R U . . .
N4 N 0.2620(2) 0.02127(13) 0.10958(11) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.354457 -0.007341 0.145248 0.032 Uiso 1 1 calc R U . . .
N1 N 0.3876(2) 0.40272(13) 0.66016(11) 0.0259(3) Uani 1 1 d . . . . .
C20 C 0.3692(2) 0.20291(14) 0.04976(11) 0.0192(3) Uani 1 1 d . . . . .
C21 C 0.2368(2) 0.13309(14) 0.04670(11) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.1123(2) 0.51973(14) 0.31621(12) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.0346(2) 0.57588(15) 0.22273(12) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.3140(2) 0.29403(14) 0.08289(11) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.4382(2) 0.35865(15) 0.08476(13) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.403099 0.419471 0.106263 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3127(2) 0.51199(15) 0.59980(12) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.0914(2) 0.61177(14) 0.35157(12) 0.0222(3) Uani 1 1 d . . . . .
C7 C 0.1504(2) 0.61168(15) 0.44109(12) 0.0239(4) Uani 1 1 d . . . . .
H7 H 0.115966 0.679600 0.453087 0.029 Uiso 1 1 calc R U . . .
O5 O -0.0307(3) 0.0560(2) 0.59614(19) 0.0721(7) Uani 1 1 d D . . . .
C11 C 0.0288(2) 0.51862(16) 0.16006(13) 0.0243(4) Uani 1 1 d . . . . .
H11 H -0.019915 0.558223 0.097677 0.029 Uiso 1 1 calc R U . . .
O4 O 0.1727(3) -0.0777(2) 0.56525(18) 0.0726(7) Uani 1 1 d . . . . .
C19 C 0.5455(2) 0.17789(16) 0.01986(14) 0.0255(4) Uani 1 1 d . . . . .
H19 H 0.581465 0.117333 -0.001913 0.031 Uiso 1 1 calc R U . . .
C12 C 0.0992(2) 0.40032(16) 0.19614(13) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.1821(2) 0.39847(15) 0.35090(13) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.233124 0.358684 0.412646 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2975(3) 0.60636(16) 0.62746(13) 0.0271(4) Uani 1 1 d . . . . .
H4A H 0.249359 0.681937 0.584679 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6693(2) 0.24247(17) 0.02209(14) 0.0286(4) Uani 1 1 d . . . . .
H18 H 0.787330 0.225426 0.002032 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6137(2) 0.33243(16) 0.05465(13) 0.0263(4) Uani 1 1 d . . . . .
H17 H 0.695447 0.375948 0.056330 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2510(2) 0.52007(16) 0.50716(13) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.285801 0.453853 0.492689 0.030 Uiso 1 1 calc R U . . .
C1 C 0.4422(3) 0.38385(17) 0.74901(14) 0.0305(4) Uani 1 1 d . . . . .
H1 H 0.492258 0.307949 0.790245 0.037 Uiso 1 1 calc R U . . .
C23 C 0.4632(3) 0.13233(16) 0.66409(15) 0.0314(4) Uani 1 1 d . . . . .
C13 C 0.1730(3) 0.34012(16) 0.29134(14) 0.0280(4) Uani 1 1 d . . . . .
H13 H 0.216080 0.259841 0.314082 0.034 Uiso 1 1 calc R U . . .
C25 C 0.4042(3) -0.06855(17) 0.69740(16) 0.0379(5) Uani 1 1 d . . . . .
H25A H 0.453309 -0.096965 0.762447 0.045 Uiso 1 1 calc R U . . .
H25B H 0.435722 -0.131262 0.673890 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3551(3) 0.58576(18) 0.71948(15) 0.0322(4) Uani 1 1 d . . . . .
H3A H 0.345473 0.647436 0.739294 0.039 Uiso 1 1 calc R U . . .
C24 C 0.4861(3) 0.03579(18) 0.62657(17) 0.0381(5) Uani 1 1 d . . . . .
H24A H 0.611963 0.009626 0.616589 0.046 Uiso 1 1 calc R U . . .
H24B H 0.431492 0.067142 0.562709 0.046 Uiso 1 1 calc R U . . .
C22 C 0.1361(3) -0.05388(19) 0.11931(18) 0.0415(5) Uani 1 1 d . . . . .
H22A H 0.146670 -0.071358 0.061348 0.062 Uiso 1 1 calc R U . . .
H22B H 0.017361 -0.014299 0.125790 0.062 Uiso 1 1 calc R U . . .
H22C H 0.161109 -0.125581 0.177192 0.062 Uiso 1 1 calc R U . . .
C2 C 0.4273(3) 0.47247(18) 0.78183(14) 0.0320(4) Uani 1 1 d . . . . .
H2 H 0.464767 0.456631 0.844385 0.038 Uiso 1 1 calc R U . . .
C27 C 0.1144(3) -0.0214(2) 0.61624(19) 0.0435(5) Uani 1 1 d . . . . .
C26 C 0.2021(3) -0.0380(2) 0.70692(17) 0.0458(6) Uani 1 1 d . . . . .
H26A H 0.158904 -0.100465 0.763869 0.055 Uiso 1 1 calc R U . . .
H26B H 0.170015 0.033467 0.718625 0.055 Uiso 1 1 calc R U . . .
H5 H -0.060(7) 0.061(5) 0.539(2) 0.14(2) 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 1.7802(17) . ?
S1 C12 1.7776(18) . ?
O1 C21 1.236(2) . ?
O2 H2A 0.8200 . ?
O2 C23 1.305(2) . ?
O3 C23 1.218(3) . ?
N2 N3 1.350(2) . ?
N2 C8 1.337(2) . ?
N3 H3 0.8600 . ?
N3 C10 1.357(2) . ?
N4 H4 0.8600 . ?
N4 C21 1.326(2) . ?
N4 C22 1.455(2) . ?
N1 C5 1.349(2) . ?
N1 C1 1.338(2) . ?
C20 C21 1.501(2) . ?
C20 C15 1.404(2) . ?
C20 C19 1.388(2) . ?
C9 C10 1.408(2) . ?
C9 C8 1.439(2) . ?
C9 C14 1.411(2) . ?
C10 C11 1.403(2) . ?
C15 C16 1.395(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C5 C4 1.397(2) . ?
C5 C6 1.460(2) . ?
C8 C7 1.449(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.331(3) . ?
O5 C27 1.295(3) . ?
O5 H5 0.870(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
O4 C27 1.227(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.394(3) . ?
C12 C13 1.417(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(3) . ?
C4 H4A 0.9300 . ?
C4 C3 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.385(3) . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.378(3) . ?
C23 C24 1.513(3) . ?
C13 H13 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C24 1.516(3) . ?
C25 C26 1.526(3) . ?
C3 H3A 0.9300 . ?
C3 C2 1.386(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C2 H2 0.9300 . ?
C27 C26 1.491(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 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 101.64(8) . . ?
C23 O2 H2A 109.5 . . ?
C8 N2 N3 106.28(14) . . ?
N2 N3 H3 123.8 . . ?
N2 N3 C10 112.38(14) . . ?
C10 N3 H3 123.8 . . ?
C21 N4 H4 119.4 . . ?
C21 N4 C22 121.15(17) . . ?
C22 N4 H4 119.4 . . ?
C1 N1 C5 119.57(16) . . ?
C15 C20 C21 119.75(14) . . ?
C19 C20 C21 120.32(15) . . ?
C19 C20 C15 119.94(15) . . ?
O1 C21 N4 123.38(16) . . ?
O1 C21 C20 120.98(14) . . ?
N4 C21 C20 115.64(14) . . ?
C10 C9 C8 103.89(14) . . ?
C10 C9 C14 118.62(16) . . ?
C14 C9 C8 137.48(16) . . ?
N3 C10 C9 106.90(15) . . ?
N3 C10 C11 129.65(16) . . ?
C11 C10 C9 123.45(16) . . ?
C20 C15 S1 118.38(13) . . ?
C16 C15 S1 122.50(13) . . ?
C16 C15 C20 119.12(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.16(16) . . ?
C17 C16 H16 119.9 . . ?
N1 C5 C4 120.78(16) . . ?
N1 C5 C6 114.30(15) . . ?
C4 C5 C6 124.91(16) . . ?
N2 C8 C9 110.53(15) . . ?
N2 C8 C7 118.39(15) . . ?
C9 C8 C7 131.05(15) . . ?
C8 C7 H7 118.1 . . ?
C6 C7 C8 123.86(16) . . ?
C6 C7 H7 118.1 . . ?
C27 O5 H5 104(4) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 C10 116.29(16) . . ?
C12 C11 H11 121.9 . . ?
C20 C19 H19 119.6 . . ?
C20 C19 C18 120.76(16) . . ?
C18 C19 H19 119.6 . . ?
C11 C12 S1 118.54(14) . . ?
C11 C12 C13 121.74(17) . . ?
C13 C12 S1 119.66(14) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 C9 118.65(17) . . ?
C13 C14 H14 120.7 . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 C5 119.07(17) . . ?
C3 C4 H4A 120.5 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 118.95(16) . . ?
C17 C18 H18 120.5 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.07(16) . . ?
C18 C17 H17 119.5 . . ?
C5 C6 H6 116.4 . . ?
C7 C6 C5 127.25(17) . . ?
C7 C6 H6 116.4 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.58(18) . . ?
C2 C1 H1 118.7 . . ?
O2 C23 C24 114.01(17) . . ?
O3 C23 O2 122.96(18) . . ?
O3 C23 C24 123.03(18) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.20(17) . . ?
C14 C13 H13 119.4 . . ?
H25A C25 H25B 107.9 . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C24 C25 C26 112.35(18) . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C4 C3 H3A 120.3 . . ?
C4 C3 C2 119.47(18) . . ?
C2 C3 H3A 120.3 . . ?
C23 C24 C25 112.77(18) . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
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 . . ?
C1 C2 C3 118.50(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
O5 C27 C26 114.7(2) . . ?
O4 C27 O5 122.3(2) . . ?
O4 C27 C26 123.0(2) . . ?
C25 C26 H26A 109.2 . . ?
C25 C26 H26B 109.2 . . ?
C27 C26 C25 112.19(19) . . ?
C27 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?

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
O2 H2A N1 0.82 1.78 2.592(2) 171.8 .
N3 H3 O1 0.86 1.99 2.788(2) 153.3 2_565
N4 H4 O3 0.86 1.98 2.817(2) 162.4 2_656
O5 H5 O4 0.870(19) 1.78(2) 2.631(3) 166(6) 2_556

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 178.81(13) . . . . ?
S1 C12 C13 C14 -179.12(14) . . . . ?
O2 C23 C24 C25 -141.9(2) . . . . ?
O3 C23 C24 C25 38.1(3) . . . . ?
N2 N3 C10 C9 0.4(2) . . . . ?
N2 N3 C10 C11 -179.13(17) . . . . ?
N2 C8 C7 C6 -173.48(17) . . . . ?
N3 N2 C8 C9 -1.00(19) . . . . ?
N3 N2 C8 C7 177.43(15) . . . . ?
N3 C10 C11 C12 -178.41(17) . . . . ?
N1 C5 C4 C3 -2.1(3) . . . . ?
N1 C5 C6 C7 169.51(18) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
C20 C15 C16 C17 -0.3(3) . . . . ?
C20 C19 C18 C17 0.0(3) . . . . ?
C21 C20 C15 S1 1.2(2) . . . . ?
C21 C20 C15 C16 -179.61(14) . . . . ?
C21 C20 C19 C18 179.78(16) . . . . ?
C9 C10 C11 C12 2.1(3) . . . . ?
C9 C8 C7 C6 4.6(3) . . . . ?
C9 C14 C13 C12 1.5(3) . . . . ?
C10 C9 C8 N2 1.23(19) . . . . ?
C10 C9 C8 C7 -176.93(17) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 S1 177.36(12) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C15 S1 C12 C11 108.91(15) . . . . ?
C15 S1 C12 C13 -73.81(16) . . . . ?
C15 C20 C21 O1 65.7(2) . . . . ?
C15 C20 C21 N4 -113.38(17) . . . . ?
C15 C20 C19 C18 -0.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C5 N1 C1 C2 -0.8(3) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C8 N2 N3 C10 0.4(2) . . . . ?
C8 C9 C10 N3 -0.95(18) . . . . ?
C8 C9 C10 C11 178.63(15) . . . . ?
C8 C9 C14 C13 178.97(19) . . . . ?
C8 C7 C6 C5 -178.61(16) . . . . ?
O5 C27 C26 C25 -147.2(2) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
O4 C27 C26 C25 34.0(4) . . . . ?
C19 C20 C21 O1 -114.23(19) . . . . ?
C19 C20 C21 N4 66.7(2) . . . . ?
C19 C20 C15 S1 -178.86(13) . . . . ?
C19 C20 C15 C16 0.3(2) . . . . ?
C19 C18 C17 C16 0.0(3) . . . . ?
C12 S1 C15 C20 159.99(13) . . . . ?
C12 S1 C15 C16 -19.13(16) . . . . ?
C14 C9 C10 N3 177.85(15) . . . . ?
C14 C9 C10 C11 -2.6(3) . . . . ?
C14 C9 C8 N2 -177.2(2) . . . . ?
C14 C9 C8 C7 4.6(3) . . . . ?
C4 C5 C6 C7 -10.0(3) . . . . ?
C4 C3 C2 C1 1.2(3) . . . . ?
C6 C5 C4 C3 177.36(17) . . . . ?
C1 N1 C5 C4 2.3(3) . . . . ?
C1 N1 C5 C6 -177.18(16) . . . . ?
C24 C25 C26 C27 72.6(3) . . . . ?
C22 N4 C21 O1 -3.6(3) . . . . ?
C22 N4 C21 C20 175.46(16) . . . . ?
C26 C25 C24 C23 66.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
