# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_ar1603
_database_code_depnum_ccdc_archive 'CCDC 2495782'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-S6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O6 S'
_chemical_melting_point          ?


_exptl_crystal_description       plate

_exptl_crystal_colour            'clear intense colourless'

_diffrn_ambient_temperature      120
_chemical_formula_weight         479.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   8.5686(2)
_cell_length_b                   15.0194(3)
_cell_length_c                   19.9522(5)
_cell_angle_alpha                106.8051(19)
_cell_angle_beta                 98.9673(19)
_cell_angle_gamma                101.7024(18)
_cell_volume                     2343.13(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120

_cell_measurement_reflns_used    36818

_cell_measurement_theta_min      2.2550

_cell_measurement_theta_max      30.6340

_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.266

_exptl_crystal_size_mid          0.180

_exptl_crystal_size_min          0.127

_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.92462

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            53965
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10732
_reflns_number_gt                9479
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.9921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10732
_refine_ls_number_parameters     813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N -0.93701(14) -0.55709(9) 0.71778(7) 0.0345(3) Uani 1 1 d . . . . .
O2 O -0.98357(14) -0.64086(8) 0.67741(8) 0.0528(3) Uani 1 1 d . . . . .
C1 C -0.77064(15) -0.50154(9) 0.72232(8) 0.0265(3) Uani 1 1 d . . . . .
C2 C -0.69749(17) -0.41895(10) 0.78110(8) 0.0294(3) Uani 1 1 d . . . . .
H1 H -0.753(2) -0.4001(12) 0.8179(9) 0.036(4) Uiso 1 1 d . . . . .
C3 C -0.54141(17) -0.36614(10) 0.78438(8) 0.0298(3) Uani 1 1 d . . . . .
H2 H -0.486(2) -0.3096(13) 0.8248(10) 0.042(5) Uiso 1 1 d . . . . .
C4 C -0.46661(15) -0.39686(9) 0.72850(8) 0.0265(3) Uani 1 1 d . . . . .
C5 C -0.54071(17) -0.47884(10) 0.66959(8) 0.0297(3) Uani 1 1 d . . . . .
H3 H -0.485(2) -0.4970(12) 0.6304(9) 0.037(4) Uiso 1 1 d . . . . .
C6 C -0.69523(17) -0.53313(10) 0.66697(8) 0.0300(3) Uani 1 1 d . . . . .
H4 H -0.747(2) -0.5903(13) 0.6270(9) 0.036(4) Uiso 1 1 d . . . . .
C12 C 0.17573(16) -0.22071(9) 0.74616(7) 0.0246(3) Uani 1 1 d . . . . .
H7 H 0.256(2) -0.2531(12) 0.7526(9) 0.032(4) Uiso 1 1 d . . . . .
C13 C 0.01244(15) -0.26648(9) 0.73684(7) 0.0242(3) Uani 1 1 d . . . . .
H8 H -0.0208(18) -0.3312(12) 0.7359(8) 0.026(4) Uiso 1 1 d . . . . .
C14 C 0.49383(14) -0.07363(9) 0.81570(7) 0.0222(2) Uani 1 1 d . . . . .
O6 O 0.46055(11) -0.11647(7) 0.85615(5) 0.0309(2) Uani 1 1 d . . . . .
C15 C 0.65646(14) -0.00963(9) 0.82247(6) 0.0212(2) Uani 1 1 d . . . . .
C16 C 0.66866(16) 0.05971(9) 0.78806(7) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.572(2) 0.0617(12) 0.7591(9) 0.034(4) Uiso 1 1 d . . . . .
C17 C 0.81825(17) 0.12245(10) 0.79560(7) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.821(2) 0.1663(12) 0.7694(9) 0.035(4) Uiso 1 1 d . . . . .
C18 C 0.95701(16) 0.11749(9) 0.83916(7) 0.0268(3) Uani 1 1 d . . . . .
H11 H 1.063(2) 0.1603(12) 0.8455(9) 0.032(4) Uiso 1 1 d . . . . .
C19 C 0.94688(15) 0.04960(9) 0.87402(7) 0.0239(2) Uani 1 1 d . . . . .
H12 H 1.042(2) 0.0461(12) 0.9029(9) 0.031(4) Uiso 1 1 d . . . . .
C20 C 0.79770(14) -0.01664(9) 0.86551(6) 0.0210(2) Uani 1 1 d . . . . .
S1 S 0.78849(4) -0.10917(2) 0.90437(2) 0.02364(8) Uani 1 1 d . . . . .
O5 O 0.38158(10) -0.07587(7) 0.75767(5) 0.02427(19) Uani 1 1 d . . . . .
C21 C 0.99913(15) -0.11857(9) 0.91976(7) 0.0238(2) Uani 1 1 d . . . . .
H13 H 1.0429(19) -0.1151(11) 0.8788(9) 0.026(4) Uiso 1 1 d . . . . .
H14 H 1.0648(18) -0.0660(11) 0.9616(8) 0.024(4) Uiso 1 1 d . . . . .
C22 C 0.99262(17) -0.21640(10) 0.92998(8) 0.0296(3) Uani 1 1 d . . . . .
H15 H 0.954(2) -0.2164(12) 0.9732(9) 0.032(4) Uiso 1 1 d . . . . .
H16 H 0.910(2) -0.2689(13) 0.8887(10) 0.039(5) Uiso 1 1 d . . . . .
C23 C 1.15635(18) -0.24274(10) 0.93302(8) 0.0308(3) Uani 1 1 d . . . . .
H17 H 1.140(2) -0.3118(13) 0.9346(9) 0.040(5) Uiso 1 1 d . . . . .
H18 H 1.194(2) -0.2426(12) 0.8879(9) 0.034(4) Uiso 1 1 d . . . . .
C24 C 1.29304(17) -0.17817(11) 0.99742(8) 0.0316(3) Uani 1 1 d . . . . .
H19 H 1.312(2) -0.1116(13) 0.9969(9) 0.040(5) Uiso 1 1 d . . . . .
H20 H 1.258(2) -0.1766(12) 1.0436(10) 0.039(4) Uiso 1 1 d . . . . .
C25 C 1.45069(18) -0.21072(12) 0.99734(8) 0.0347(3) Uani 1 1 d . . . . .
H21 H 1.4326(19) -0.2757(12) 0.9954(8) 0.027(4) Uiso 1 1 d . . . . .
H22 H 1.482(2) -0.2149(13) 0.9504(10) 0.042(5) Uiso 1 1 d . . . . .
C26 C 1.5910(2) -0.14529(15) 1.05927(10) 0.0434(4) Uani 1 1 d . . . . .
H23 H 1.563(2) -0.1396(14) 1.1066(11) 0.048(5) Uiso 1 1 d . . . . .
H24 H 1.688(3) -0.1700(15) 1.0572(11) 0.057(6) Uiso 1 1 d . . . . .
H25 H 1.619(3) -0.0794(16) 1.0572(11) 0.057(6) Uiso 1 1 d . . . . .
N2 N -1.16795(17) -0.44502(10) 0.56429(7) 0.0436(3) Uani 1 1 d . . . . .
O7 O -1.30456(16) -0.43846(12) 0.54178(9) 0.0702(4) Uani 1 1 d . . . . .
O8 O -1.14330(17) -0.50645(10) 0.59049(7) 0.0601(4) Uani 1 1 d . . . . .
C27 C -1.02560(17) -0.37529(10) 0.55980(7) 0.0295(3) Uani 1 1 d . . . . .
C28 C -1.04984(16) -0.29910(11) 0.53793(8) 0.0308(3) Uani 1 1 d . . . . .
H26 H -1.157(2) -0.2934(12) 0.5238(9) 0.037(4) Uiso 1 1 d . . . . .
C29 C -0.91491(16) -0.22943(10) 0.53818(8) 0.0281(3) Uani 1 1 d . . . . .
H27 H -0.933(2) -0.1771(13) 0.5224(10) 0.042(5) Uiso 1 1 d . . . . .
C30 C -0.75994(15) -0.23859(9) 0.56172(7) 0.0221(2) Uani 1 1 d . . . . .
C31 C -0.73669(17) -0.31746(10) 0.58075(7) 0.0285(3) Uani 1 1 d . . . . .
H28 H -0.627(2) -0.3217(12) 0.5951(9) 0.039(4) Uiso 1 1 d . . . . .
C32 C -0.87148(18) -0.38685(10) 0.57989(8) 0.0327(3) Uani 1 1 d . . . . .
H29 H -0.861(2) -0.4394(13) 0.5928(9) 0.040(5) Uiso 1 1 d . . . . .
O9 O -0.61567(10) -0.17352(6) 0.56459(5) 0.02528(19) Uani 1 1 d . . . . .
C33 C -0.59787(15) -0.07561(9) 0.58672(7) 0.0224(2) Uani 1 1 d . . . . .
O10 O -0.70600(11) -0.03859(7) 0.60000(6) 0.0323(2) Uani 1 1 d . . . . .
C34 C -0.42722(14) -0.02405(9) 0.59091(6) 0.0211(2) Uani 1 1 d . . . . .
C35 C -0.39643(16) 0.07272(9) 0.59555(7) 0.0253(3) Uani 1 1 d . . . . .
H30 H -0.484(2) 0.1029(12) 0.5965(9) 0.036(4) Uiso 1 1 d . . . . .
C36 C -0.23979(16) 0.12430(9) 0.59863(7) 0.0261(3) Uani 1 1 d . . . . .
H31 H -0.2165(19) 0.1897(12) 0.6017(8) 0.028(4) Uiso 1 1 d . . . . .
C37 C -0.11582(14) 0.07804(9) 0.59727(7) 0.0221(2) Uani 1 1 d . . . . .
C38 C -0.14198(15) -0.01734(9) 0.59397(7) 0.0248(3) Uani 1 1 d . . . . .
H32 H -0.055(2) -0.0482(12) 0.5944(9) 0.037(4) Uiso 1 1 d . . . . .
C39 C -0.29901(15) -0.06858(9) 0.59070(7) 0.0233(2) Uani 1 1 d . . . . .
H33 H -0.320(2) -0.1344(12) 0.5884(9) 0.033(4) Uiso 1 1 d . . . . .
O11 O 0.03851(10) 0.13035(7) 0.59573(5) 0.02518(19) Uani 1 1 d . . . . .
C40 C 0.15789(14) 0.16112(8) 0.65769(7) 0.0213(2) Uani 1 1 d . . . . .
O12 O 0.13468(11) 0.14224(7) 0.71040(5) 0.0321(2) Uani 1 1 d . . . . .
C41 C 0.31210(14) 0.21917(8) 0.65016(7) 0.0205(2) Uani 1 1 d . . . . .
C42 C 0.32563(15) 0.22541(9) 0.58256(7) 0.0233(2) Uani 1 1 d . . . . .
H34 H 0.2356(19) 0.1903(11) 0.5427(8) 0.025(4) Uiso 1 1 d . . . . .
C43 C 0.46771(16) 0.27882(9) 0.57301(8) 0.0268(3) Uani 1 1 d . . . . .
H35 H 0.4721(19) 0.2831(11) 0.5259(9) 0.029(4) Uiso 1 1 d . . . . .
C44 C 0.59915(16) 0.32520(9) 0.63157(8) 0.0269(3) Uani 1 1 d . . . . .
H36 H 0.696(2) 0.3610(12) 0.6251(9) 0.034(4) Uiso 1 1 d . . . . .
C45 C 0.58914(15) 0.31944(9) 0.69873(8) 0.0261(3) Uani 1 1 d . . . . .
H37 H 0.684(2) 0.3542(11) 0.7387(9) 0.029(4) Uiso 1 1 d . . . . .
C46 C 0.44504(15) 0.26753(9) 0.71015(7) 0.0222(2) Uani 1 1 d . . . . .
S2 S 0.42987(4) 0.26067(2) 0.79592(2) 0.02976(9) Uani 1 1 d . . . . .
O3 O -0.30603(11) -0.34790(7) 0.73264(6) 0.0321(2) Uani 1 1 d . . . . .
O1 O -1.02089(13) -0.51645(9) 0.75424(7) 0.0448(3) Uani 1 1 d . . . . .
C7 C -0.28321(15) -0.26165(9) 0.71988(7) 0.0228(2) Uani 1 1 d . . . . .
O4 O -0.39493(11) -0.22899(7) 0.70405(6) 0.0306(2) Uani 1 1 d . . . . .
C8 C -0.10764(14) -0.21729(9) 0.72771(6) 0.0212(2) Uani 1 1 d . . . . .
C9 C -0.06184(15) -0.12306(9) 0.72677(6) 0.0214(2) Uani 1 1 d . . . . .
H5 H -0.1396(19) -0.0894(11) 0.7211(8) 0.024(4) Uiso 1 1 d . . . . .
C10 C 0.10189(15) -0.07627(9) 0.73734(7) 0.0222(2) Uani 1 1 d . . . . .
H6 H 0.1360(19) -0.0103(12) 0.7375(8) 0.027(4) Uiso 1 1 d . . . . .
C11 C 0.21865(14) -0.12561(9) 0.74812(6) 0.0212(2) Uani 1 1 d . . . . .
C47 C 0.60568(18) 0.35498(10) 0.85603(8) 0.0328(3) Uani 1 1 d . . . . .
H38 H 0.605(2) 0.3422(13) 0.9010(10) 0.041(5) Uiso 1 1 d . . . . .
H39 H 0.707(2) 0.3456(13) 0.8421(10) 0.041(5) Uiso 1 1 d . . . . .
C48 C 0.58825(19) 0.45659(11) 0.86425(8) 0.0347(3) Uani 1 1 d . . . . .
H40 H 0.574(2) 0.4649(12) 0.8167(10) 0.038(4) Uiso 1 1 d . . . . .
H41 H 0.483(2) 0.4621(14) 0.8819(11) 0.053(5) Uiso 1 1 d . . . . .
C49 C 0.7331(2) 0.53597(12) 0.91715(10) 0.0438(4) Uani 1 1 d . . . . .
H42 H 0.830(3) 0.5338(15) 0.8996(11) 0.059(6) Uiso 1 1 d . . . . .
H43 H 0.715(3) 0.5994(16) 0.9155(11) 0.059(6) Uiso 1 1 d . . . . .
C50 C 0.7561(2) 0.53288(14) 0.99446(10) 0.0467(4) Uani 1 1 d . . . . .
H44 H 0.652(3) 0.5307(18) 1.0112(13) 0.081(8) Uiso 1 1 d . . . . .
H45 H 0.800(3) 0.470(2) 0.9917(14) 0.093(8) Uiso 1 1 d . . . . .
C51 C 0.8839(3) 0.61731(14) 1.04945(11) 0.0556(5) Uani 1 1 d . . . . .
H46 H 0.993(4) 0.630(3) 1.0288(19) 0.137(13) Uiso 1 1 d . . . . .
H47 H 0.834(4) 0.677(3) 1.0499(17) 0.122(11) Uiso 1 1 d . . . . .
C52 C 0.9065(3) 0.61019(15) 1.12345(11) 0.0490(4) Uani 1 1 d . . . . .
H48 H 1.000(3) 0.6672(18) 1.1590(13) 0.075(7) Uiso 1 1 d . . . . .
H49 H 0.809(4) 0.609(2) 1.1400(15) 0.092(9) Uiso 1 1 d . . . . .
H50 H 0.932(3) 0.549(2) 1.1210(14) 0.083(8) 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
N1 O2 1.2252(17) . ?
N1 O1 1.2258(17) . ?
N1 C1 1.4732(16) . ?
C1 C6 1.381(2) . ?
C1 C2 1.3861(19) . ?
C2 C3 1.3908(19) . ?
C3 C4 1.383(2) . ?
C4 C5 1.3834(19) . ?
C4 O3 1.4000(15) . ?
C5 C6 1.3916(19) . ?
C12 C13 1.3855(18) . ?
C12 C11 1.3881(18) . ?
C13 C8 1.4019(17) . ?
C14 O6 1.2017(15) . ?
C14 O5 1.3726(15) . ?
C14 C15 1.4856(16) . ?
C15 C16 1.3995(18) . ?
C15 C20 1.4117(17) . ?
C16 C17 1.3862(18) . ?
C17 C18 1.388(2) . ?
C18 C19 1.3871(19) . ?
C19 C20 1.4040(17) . ?
C20 S1 1.7711(13) . ?
S1 C21 1.8242(13) . ?
O5 C11 1.3983(14) . ?
C21 C22 1.5320(19) . ?
C22 C23 1.5299(19) . ?
C23 C24 1.521(2) . ?
C24 C25 1.527(2) . ?
C25 C26 1.514(2) . ?
N2 O7 1.221(2) . ?
N2 O8 1.222(2) . ?
N2 C27 1.4706(17) . ?
C27 C28 1.378(2) . ?
C27 C32 1.380(2) . ?
C28 C29 1.3915(18) . ?
C29 C30 1.3856(18) . ?
C30 C31 1.3853(19) . ?
C30 O9 1.3936(14) . ?
C31 C32 1.3842(19) . ?
O9 C33 1.3758(15) . ?
C33 O10 1.1992(16) . ?
C33 C34 1.4866(16) . ?
C34 C35 1.3963(17) . ?
C34 C39 1.3971(18) . ?
C35 C36 1.3893(17) . ?
C36 C37 1.3818(18) . ?
C37 C38 1.3846(18) . ?
C37 O11 1.4043(14) . ?
C38 C39 1.3895(17) . ?
O11 C40 1.3681(15) . ?
C40 O12 1.2003(15) . ?
C40 C41 1.4830(16) . ?
C41 C42 1.3996(18) . ?
C41 C46 1.4122(18) . ?
C42 C43 1.3880(17) . ?
C43 C44 1.386(2) . ?
C44 C45 1.382(2) . ?
C45 C46 1.4086(17) . ?
C46 S2 1.7670(13) . ?
S2 C47 1.8174(14) . ?
O3 C7 1.3728(15) . ?
C7 O4 1.2011(15) . ?
C7 C8 1.4803(16) . ?
C8 C9 1.3964(17) . ?
C9 C10 1.3888(17) . ?
C10 C11 1.3865(17) . ?
C47 C48 1.528(2) . ?
C48 C49 1.530(2) . ?
C49 C50 1.540(3) . ?
C50 C51 1.506(2) . ?
C51 C52 1.496(3) . ?

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
O2 N1 O1 123.98(12) . . ?
O2 N1 C1 118.03(13) . . ?
O1 N1 C1 117.98(12) . . ?
C6 C1 C2 122.72(12) . . ?
C6 C1 N1 118.43(12) . . ?
C2 C1 N1 118.84(13) . . ?
C1 C2 C3 118.44(13) . . ?
C4 C3 C2 118.94(13) . . ?
C3 C4 C5 122.42(12) . . ?
C3 C4 O3 119.82(12) . . ?
C5 C4 O3 117.63(12) . . ?
C4 C5 C6 118.78(13) . . ?
C1 C6 C5 118.66(13) . . ?
C13 C12 C11 119.37(12) . . ?
C12 C13 C8 119.81(12) . . ?
O6 C14 O5 123.23(11) . . ?
O6 C14 C15 125.54(11) . . ?
O5 C14 C15 111.19(10) . . ?
C16 C15 C20 120.07(11) . . ?
C16 C15 C14 119.90(11) . . ?
C20 C15 C14 120.00(11) . . ?
C17 C16 C15 120.96(12) . . ?
C16 C17 C18 119.30(12) . . ?
C19 C18 C17 120.47(12) . . ?
C18 C19 C20 121.29(12) . . ?
C19 C20 C15 117.86(11) . . ?
C19 C20 S1 121.06(10) . . ?
C15 C20 S1 121.03(9) . . ?
C20 S1 C21 103.22(6) . . ?
C14 O5 C11 117.99(9) . . ?
C22 C21 S1 106.42(9) . . ?
C23 C22 C21 113.48(12) . . ?
C24 C23 C22 115.28(12) . . ?
C23 C24 C25 111.95(13) . . ?
C26 C25 C24 113.08(14) . . ?
O7 N2 O8 123.39(14) . . ?
O7 N2 C27 118.35(14) . . ?
O8 N2 C27 118.26(14) . . ?
C28 C27 C32 122.21(12) . . ?
C28 C27 N2 119.14(13) . . ?
C32 C27 N2 118.62(13) . . ?
C27 C28 C29 119.35(13) . . ?
C30 C29 C28 118.38(13) . . ?
C31 C30 C29 121.86(12) . . ?
C31 C30 O9 114.31(11) . . ?
C29 C30 O9 123.73(11) . . ?
C32 C31 C30 119.36(13) . . ?
C27 C32 C31 118.70(13) . . ?
C33 O9 C30 122.01(10) . . ?
O10 C33 O9 124.15(11) . . ?
O10 C33 C34 125.78(11) . . ?
O9 C33 C34 110.06(10) . . ?
C35 C34 C39 119.70(11) . . ?
C35 C34 C33 117.75(11) . . ?
C39 C34 C33 122.55(11) . . ?
C36 C35 C34 120.35(12) . . ?
C37 C36 C35 118.70(12) . . ?
C36 C37 C38 122.28(11) . . ?
C36 C37 O11 117.21(11) . . ?
C38 C37 O11 120.44(11) . . ?
C37 C38 C39 118.72(12) . . ?
C38 C39 C34 120.23(12) . . ?
C40 O11 C37 116.73(9) . . ?
O12 C40 O11 122.18(11) . . ?
O12 C40 C41 126.37(12) . . ?
O11 C40 C41 111.45(10) . . ?
C42 C41 C46 119.87(11) . . ?
C42 C41 C40 119.33(11) . . ?
C46 C41 C40 120.80(11) . . ?
C43 C42 C41 121.28(12) . . ?
C44 C43 C42 118.96(12) . . ?
C45 C44 C43 120.80(12) . . ?
C44 C45 C46 121.32(12) . . ?
C45 C46 C41 117.75(12) . . ?
C45 C46 S2 121.78(10) . . ?
C41 C46 S2 120.46(9) . . ?
C46 S2 C47 103.27(7) . . ?
C7 O3 C4 117.43(10) . . ?
O4 C7 O3 122.54(11) . . ?
O4 C7 C8 126.07(12) . . ?
O3 C7 C8 111.39(10) . . ?
C9 C8 C13 119.65(11) . . ?
C9 C8 C7 118.30(11) . . ?
C13 C8 C7 122.04(11) . . ?
C10 C9 C8 120.74(11) . . ?
C11 C10 C9 118.47(12) . . ?
C10 C11 C12 121.85(11) . . ?
C10 C11 O5 116.33(11) . . ?
C12 C11 O5 121.75(11) . . ?
C48 C47 S2 113.41(10) . . ?
C47 C48 C49 113.45(13) . . ?
C48 C49 C50 113.34(14) . . ?
C51 C50 C49 114.48(15) . . ?
C52 C51 C50 112.92(17) . . ?

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
O2 N1 C1 C6 19.99(19) . . . . ?
O1 N1 C1 C6 -159.49(13) . . . . ?
O2 N1 C1 C2 -161.18(14) . . . . ?
O1 N1 C1 C2 19.34(19) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C2 C3 -179.01(12) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C2 C3 C4 O3 -176.39(12) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
O3 C4 C5 C6 174.95(12) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
N1 C1 C6 C5 177.49(12) . . . . ?
C4 C5 C6 C1 1.8(2) . . . . ?
C11 C12 C13 C8 1.60(19) . . . . ?
O6 C14 C15 C16 -158.95(13) . . . . ?
O5 C14 C15 C16 19.09(16) . . . . ?
O6 C14 C15 C20 18.95(19) . . . . ?
O5 C14 C15 C20 -163.02(11) . . . . ?
C20 C15 C16 C17 -0.14(19) . . . . ?
C14 C15 C16 C17 177.76(12) . . . . ?
C15 C16 C17 C18 -1.4(2) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C20 1.0(2) . . . . ?
C18 C19 C20 C15 -2.45(18) . . . . ?
C18 C19 C20 S1 174.94(10) . . . . ?
C16 C15 C20 C19 2.00(18) . . . . ?
C14 C15 C20 C19 -175.89(11) . . . . ?
C16 C15 C20 S1 -175.39(10) . . . . ?
C14 C15 C20 S1 6.72(16) . . . . ?
C19 C20 S1 C21 -20.31(12) . . . . ?
C15 C20 S1 C21 156.99(10) . . . . ?
O6 C14 O5 C11 4.15(18) . . . . ?
C15 C14 O5 C11 -173.94(10) . . . . ?
C20 S1 C21 C22 -162.05(9) . . . . ?
S1 C21 C22 C23 171.86(10) . . . . ?
C21 C22 C23 C24 65.48(16) . . . . ?
C22 C23 C24 C25 178.64(12) . . . . ?
C23 C24 C25 C26 177.67(13) . . . . ?
O7 N2 C27 C28 7.0(2) . . . . ?
O8 N2 C27 C28 -172.84(15) . . . . ?
O7 N2 C27 C32 -174.99(16) . . . . ?
O8 N2 C27 C32 5.1(2) . . . . ?
C32 C27 C28 C29 -2.2(2) . . . . ?
N2 C27 C28 C29 175.75(13) . . . . ?
C27 C28 C29 C30 -1.0(2) . . . . ?
C28 C29 C30 C31 3.8(2) . . . . ?
C28 C29 C30 O9 -179.88(12) . . . . ?
C29 C30 C31 C32 -3.4(2) . . . . ?
O9 C30 C31 C32 179.96(12) . . . . ?
C28 C27 C32 C31 2.6(2) . . . . ?
N2 C27 C32 C31 -175.33(13) . . . . ?
C30 C31 C32 C27 0.2(2) . . . . ?
C31 C30 O9 C33 -143.46(12) . . . . ?
C29 C30 O9 C33 39.98(18) . . . . ?
C30 O9 C33 O10 -5.81(19) . . . . ?
C30 O9 C33 C34 174.66(10) . . . . ?
O10 C33 C34 C35 -14.55(19) . . . . ?
O9 C33 C34 C35 164.98(11) . . . . ?
O10 C33 C34 C39 165.13(13) . . . . ?
O9 C33 C34 C39 -15.34(16) . . . . ?
C39 C34 C35 C36 1.17(19) . . . . ?
C33 C34 C35 C36 -179.14(12) . . . . ?
C34 C35 C36 C37 -0.2(2) . . . . ?
C35 C36 C37 C38 -0.9(2) . . . . ?
C35 C36 C37 O11 175.96(11) . . . . ?
C36 C37 C38 C39 1.1(2) . . . . ?
O11 C37 C38 C39 -175.68(11) . . . . ?
C37 C38 C39 C34 -0.11(19) . . . . ?
C35 C34 C39 C38 -1.00(19) . . . . ?
C33 C34 C39 C38 179.33(12) . . . . ?
C36 C37 O11 C40 107.01(13) . . . . ?
C38 C37 O11 C40 -76.06(15) . . . . ?
C37 O11 C40 O12 2.23(17) . . . . ?
C37 O11 C40 C41 -177.32(10) . . . . ?
O12 C40 C41 C42 172.64(13) . . . . ?
O11 C40 C41 C42 -7.83(16) . . . . ?
O12 C40 C41 C46 -7.0(2) . . . . ?
O11 C40 C41 C46 172.50(11) . . . . ?
C46 C41 C42 C43 -0.25(18) . . . . ?
C40 C41 C42 C43 -179.93(11) . . . . ?
C41 C42 C43 C44 1.17(19) . . . . ?
C42 C43 C44 C45 -0.6(2) . . . . ?
C43 C44 C45 C46 -0.8(2) . . . . ?
C44 C45 C46 C41 1.70(18) . . . . ?
C44 C45 C46 S2 -179.30(10) . . . . ?
C42 C41 C46 C45 -1.16(17) . . . . ?
C40 C41 C46 C45 178.51(11) . . . . ?
C42 C41 C46 S2 179.83(9) . . . . ?
C40 C41 C46 S2 -0.50(16) . . . . ?
C45 C46 S2 C47 14.22(12) . . . . ?
C41 C46 S2 C47 -166.82(10) . . . . ?
C3 C4 O3 C7 -76.94(16) . . . . ?
C5 C4 O3 C7 107.05(14) . . . . ?
C4 O3 C7 O4 -1.69(19) . . . . ?
C4 O3 C7 C8 178.72(11) . . . . ?
C12 C13 C8 C9 1.16(19) . . . . ?
C12 C13 C8 C7 -178.01(12) . . . . ?
O4 C7 C8 C9 9.58(19) . . . . ?
O3 C7 C8 C9 -170.84(11) . . . . ?
O4 C7 C8 C13 -171.24(13) . . . . ?
O3 C7 C8 C13 8.33(17) . . . . ?
C13 C8 C9 C10 -2.30(18) . . . . ?
C7 C8 C9 C10 176.90(11) . . . . ?
C8 C9 C10 C11 0.63(18) . . . . ?
C9 C10 C11 C12 2.23(19) . . . . ?
C9 C10 C11 O5 179.28(10) . . . . ?
C13 C12 C11 C10 -3.36(19) . . . . ?
C13 C12 C11 O5 179.75(11) . . . . ?
C14 O5 C11 C10 129.66(12) . . . . ?
C14 O5 C11 C12 -53.28(16) . . . . ?
C46 S2 C47 C48 71.30(13) . . . . ?
S2 C47 C48 C49 177.69(12) . . . . ?
C47 C48 C49 C50 -62.1(2) . . . . ?
C48 C49 C50 C51 -172.61(18) . . . . ?
C49 C50 C51 C52 -178.17(19) . . . . ?

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.042


_diffrn_radiation_monochromator  mirror

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1701
_database_code_depnum_ccdc_archive 'CCDC 2495784'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-O2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O7'
_chemical_melting_point          ?


_exptl_crystal_description       plate

_exptl_crystal_colour            'clear intense colourless'

_diffrn_ambient_temperature      120
_chemical_formula_weight         407.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'

_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.
;

_cell_length_a                   7.8746(3)
_cell_length_b                   10.5597(5)
_cell_length_c                   12.6069(6)
_cell_angle_alpha                67.675(5)
_cell_angle_beta                 89.254(4)
_cell_angle_gamma                83.238(4)
_cell_volume                     962.41(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120

_cell_measurement_reflns_used    14359

_cell_measurement_theta_min      2.2130

_cell_measurement_theta_max      29.9190

_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.327

_exptl_crystal_size_mid          0.193

_exptl_crystal_size_min          0.167

_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.71828

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21638
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.606
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             8130
_reflns_number_gt                7717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     0.847
_reflns_Friedel_fraction_full    0.931

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.1566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)

_refine_ls_number_reflns         8130
_refine_ls_number_parameters     677
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.2574(3) -0.1367(2) 0.56266(18) 0.0311(5) Uani 1 1 d . . . . .
O1 O 0.2878(3) -0.2429(2) 0.5462(2) 0.0467(5) Uani 1 1 d . . . . .
O2 O 0.1122(3) -0.0843(3) 0.5690(3) 0.0593(7) Uani 1 1 d . . . . .
C1 C 0.4009(3) -0.0672(2) 0.57820(19) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.5651(3) -0.1265(2) 0.57337(19) 0.0202(4) Uani 1 1 d . . . . .
H1 H 0.583(4) -0.209(3) 0.558(2) 0.025(7) Uiso 1 1 d . . . . .
C3 C 0.7011(3) -0.0642(2) 0.59252(19) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.815(4) -0.103(3) 0.591(3) 0.032(7) Uiso 1 1 d . . . . .
C4 C 0.6674(3) 0.0543(2) 0.61479(19) 0.0216(5) Uani 1 1 d . . . . .
C5 C 0.5022(3) 0.1163(3) 0.6159(2) 0.0279(5) Uani 1 1 d . . . . .
H3 H 0.488(4) 0.199(3) 0.632(3) 0.036(8) Uiso 1 1 d . . . . .
O3 O 0.8052(2) 0.10802(18) 0.64510(14) 0.0277(4) Uani 1 1 d . . . . .
C6 C 0.3665(3) 0.0541(3) 0.5977(2) 0.0284(5) Uani 1 1 d . . . . .
H4 H 0.245(4) 0.088(3) 0.602(3) 0.040(8) Uiso 1 1 d . . . . .
C7 C 0.8532(3) 0.2275(2) 0.56656(19) 0.0201(4) Uani 1 1 d . . . . .
O4 O 0.7950(2) 0.27944(19) 0.47064(14) 0.0307(4) Uani 1 1 d . . . . .
C8 C 0.9856(3) 0.2793(2) 0.61722(19) 0.0188(4) Uani 1 1 d . . . . .
C9 C 1.0576(3) 0.3950(2) 0.54620(19) 0.0206(4) Uani 1 1 d . . . . .
H5 H 1.020(4) 0.436(3) 0.467(3) 0.032(8) Uiso 1 1 d . . . . .
C10 C 1.1792(3) 0.4502(2) 0.5892(2) 0.0222(5) Uani 1 1 d . . . . .
H6 H 1.228(3) 0.529(3) 0.543(2) 0.020(6) Uiso 1 1 d . . . . .
C11 C 1.2266(3) 0.3876(2) 0.70500(19) 0.0202(4) Uani 1 1 d . . . . .
C12 C 1.1569(3) 0.2716(3) 0.7776(2) 0.0232(5) Uani 1 1 d . . . . .
H7 H 1.188(4) 0.232(3) 0.858(3) 0.035(8) Uiso 1 1 d . . . . .
C13 C 1.0367(3) 0.2170(2) 0.73344(19) 0.0216(5) Uani 1 1 d . . . . .
H8 H 0.987(4) 0.131(3) 0.784(3) 0.031(7) Uiso 1 1 d . . . . .
O5 O 1.3340(2) 0.44588(18) 0.75662(14) 0.0250(4) Uani 1 1 d . . . . .
C14 C 1.4931(3) 0.4685(2) 0.71523(19) 0.0201(4) Uani 1 1 d . . . . .
O6 O 1.5516(2) 0.42613(19) 0.64494(16) 0.0314(4) Uani 1 1 d . . . . .
C15 C 1.5875(3) 0.5435(2) 0.77051(19) 0.0202(4) Uani 1 1 d . . . . .
C16 C 1.7643(3) 0.5354(3) 0.7551(2) 0.0259(5) Uani 1 1 d . . . . .
H9 H 1.814(4) 0.481(3) 0.712(2) 0.026(7) Uiso 1 1 d . . . . .
C17 C 1.8693(3) 0.5991(3) 0.8022(2) 0.0311(6) Uani 1 1 d . . . . .
H10 H 1.993(4) 0.591(3) 0.793(3) 0.038(8) Uiso 1 1 d . . . . .
C18 C 1.7951(3) 0.6716(3) 0.8666(2) 0.0274(5) Uani 1 1 d . . . . .
H11 H 1.868(4) 0.718(3) 0.903(2) 0.029(7) Uiso 1 1 d . . . . .
C19 C 1.6205(3) 0.6825(2) 0.8825(2) 0.0229(5) Uani 1 1 d . . . . .
H12 H 1.574(4) 0.731(3) 0.930(2) 0.024(7) Uiso 1 1 d . . . . .
C20 C 1.5134(3) 0.6189(2) 0.83493(19) 0.0199(4) Uani 1 1 d . . . . .
O7 O 1.3421(2) 0.6273(2) 0.84703(15) 0.0291(4) Uani 1 1 d . . . . .
C21 C 1.2680(3) 0.6752(3) 0.9334(2) 0.0277(5) Uani 1 1 d . . . . .
H13 H 1.171(4) 0.625(3) 0.956(3) 0.036(8) Uiso 1 1 d . . . . .
N2 N 0.3023(3) 0.0536(2) 0.14247(18) 0.0290(5) Uani 1 1 d . . . . .
O8 O 0.2088(3) 0.1070(3) 0.05617(17) 0.0489(6) Uani 1 1 d . . . . .
O9 O 0.2958(2) -0.0634(2) 0.21202(18) 0.0367(4) Uani 1 1 d . . . . .
H14 H 1.341(4) 0.650(3) 0.996(3) 0.028(7) Uiso 1 1 d . . . . .
C22 C 1.2153(4) 0.8286(3) 0.8863(3) 0.0407(7) Uani 1 1 d . . . . .
H15 H 1.319(5) 0.880(4) 0.864(3) 0.043(9) Uiso 1 1 d . . . . .
H16 H 1.130(5) 0.859(4) 0.816(3) 0.054(10) Uiso 1 1 d . . . . .
H17 H 1.164(6) 0.854(5) 0.948(4) 0.072(12) Uiso 1 1 d . . . . .
C23 C 0.4309(3) 0.1337(3) 0.1627(2) 0.0235(5) Uani 1 1 d . . . . .
C24 C 0.4518(3) 0.2624(3) 0.0798(2) 0.0278(5) Uani 1 1 d . . . . .
H18 H 0.383(4) 0.301(3) 0.012(2) 0.024(7) Uiso 1 1 d . . . . .
C25 C 0.5813(3) 0.3314(3) 0.0978(2) 0.0271(5) Uani 1 1 d . . . . .
H19 H 0.602(4) 0.421(4) 0.042(3) 0.039(8) Uiso 1 1 d . . . . .
C26 C 0.6836(3) 0.2720(2) 0.1968(2) 0.0221(5) Uani 1 1 d . . . . .
C27 C 0.6564(3) 0.1462(2) 0.28174(19) 0.0210(4) Uani 1 1 d . . . . .
H20 H 0.723(3) 0.109(3) 0.348(2) 0.014(6) Uiso 1 1 d . . . . .
C28 C 0.5297(3) 0.0758(2) 0.26332(19) 0.0216(5) Uani 1 1 d . . . . .
H21 H 0.514(4) -0.014(3) 0.318(2) 0.026(7) Uiso 1 1 d . . . . .
O10 O 0.8094(2) 0.34883(16) 0.20973(14) 0.0242(3) Uani 1 1 d . . . . .
C29 C 0.9702(3) 0.2826(2) 0.2467(2) 0.0244(5) Uani 1 1 d . . . . .
O11 O 1.0127(2) 0.16292(19) 0.2634(2) 0.0392(5) Uani 1 1 d . . . . .
C30 C 1.0871(3) 0.3760(2) 0.26213(19) 0.0213(4) Uani 1 1 d . . . . .
C31 C 1.2422(3) 0.3132(2) 0.3219(2) 0.0238(5) Uani 1 1 d . . . . .
H22 H 1.266(4) 0.212(3) 0.352(2) 0.030(7) Uiso 1 1 d . . . . .
C32 C 1.3595(3) 0.3922(3) 0.3391(2) 0.0236(5) Uani 1 1 d . . . . .
H23 H 1.464(4) 0.352(3) 0.380(2) 0.025(7) Uiso 1 1 d . . . . .
C33 C 1.3195(3) 0.5344(2) 0.29560(19) 0.0210(5) Uani 1 1 d . . . . .
C34 C 1.1658(3) 0.5993(2) 0.2365(2) 0.0226(5) Uani 1 1 d . . . . .
H24 H 1.144(4) 0.697(4) 0.209(3) 0.042(9) Uiso 1 1 d . . . . .
C35 C 1.0481(3) 0.5195(2) 0.21991(19) 0.0211(4) Uani 1 1 d . . . . .
H25 H 0.942(4) 0.569(3) 0.174(2) 0.024(7) Uiso 1 1 d . . . . .
O12 O 1.4356(2) 0.61290(17) 0.31859(14) 0.0235(3) Uani 1 1 d . . . . .
C36 C 1.5483(3) 0.6655(2) 0.2344(2) 0.0234(5) Uani 1 1 d . . . . .
O13 O 1.5417(3) 0.6540(2) 0.14416(16) 0.0390(5) Uani 1 1 d . . . . .
C37 C 1.6796(3) 0.7296(2) 0.27398(19) 0.0210(4) Uani 1 1 d . . . . .
C38 C 1.7330(3) 0.6765(2) 0.3897(2) 0.0222(5) Uani 1 1 d . . . . .
H26 H 1.677(4) 0.602(3) 0.441(3) 0.030(7) Uiso 1 1 d . . . . .
C39 C 1.8632(3) 0.7303(2) 0.4265(2) 0.0242(5) Uani 1 1 d . . . . .
H27 H 1.899(4) 0.689(3) 0.515(2) 0.027(7) Uiso 1 1 d . . . . .
C40 C 1.9413(3) 0.8359(2) 0.3479(2) 0.0238(5) Uani 1 1 d . . . . .
H28 H 2.030(3) 0.874(3) 0.369(2) 0.014(6) Uiso 1 1 d . . . . .
C41 C 1.8893(3) 0.8915(2) 0.2325(2) 0.0239(5) Uani 1 1 d . . . . .
H29 H 1.946(3) 0.966(3) 0.177(2) 0.019(6) Uiso 1 1 d . . . . .
C42 C 1.7576(3) 0.8395(2) 0.19526(19) 0.0212(4) Uani 1 1 d . . . . .
O14 O 1.6935(2) 0.89327(18) 0.08488(14) 0.0289(4) Uani 1 1 d . . . . .
C43 C 1.7529(3) 1.0188(3) 0.0079(2) 0.0278(5) Uani 1 1 d . . . . .
H30 H 1.748(3) 1.087(3) 0.044(2) 0.022(6) Uiso 1 1 d . . . . .
H31 H 1.875(4) 0.994(3) -0.009(2) 0.023(7) Uiso 1 1 d . . . . .
C44 C 1.6378(4) 1.0684(3) -0.0982(2) 0.0378(6) Uani 1 1 d . . . . .
H32 H 1.514(4) 1.087(3) -0.082(3) 0.042(9) Uiso 1 1 d . . . . .
H33 H 1.674(4) 1.154(3) -0.155(3) 0.037(8) Uiso 1 1 d . . . . .
H34 H 1.643(5) 1.000(4) -0.137(3) 0.058(11) 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
N1 O1 1.212(3) . ?
N1 O2 1.225(3) . ?
N1 C1 1.472(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.388(3) . ?
C4 O3 1.402(3) . ?
C5 C6 1.383(4) . ?
O3 C7 1.367(3) . ?
C7 O4 1.193(3) . ?
C7 C8 1.487(3) . ?
C8 C9 1.390(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.391(3) . ?
C11 O5 1.400(3) . ?
C12 C13 1.387(3) . ?
O5 C14 1.362(3) . ?
C14 O6 1.200(3) . ?
C14 C15 1.496(3) . ?
C15 C16 1.400(3) . ?
C15 C20 1.416(3) . ?
C16 C17 1.391(4) . ?
C17 C18 1.392(4) . ?
C18 C19 1.384(3) . ?
C19 C20 1.405(3) . ?
C20 O7 1.352(3) . ?
O7 C21 1.454(3) . ?
C21 C22 1.505(4) . ?
N2 O9 1.220(3) . ?
N2 O8 1.225(3) . ?
N2 C23 1.476(3) . ?
C23 C28 1.383(3) . ?
C23 C24 1.391(3) . ?
C24 C25 1.389(3) . ?
C25 C26 1.383(3) . ?
C26 C27 1.391(3) . ?
C26 O10 1.401(3) . ?
C27 C28 1.384(3) . ?
O10 C29 1.367(3) . ?
C29 O11 1.205(3) . ?
C29 C30 1.491(3) . ?
C30 C31 1.398(3) . ?
C30 C35 1.398(3) . ?
C31 C32 1.385(3) . ?
C32 C33 1.386(3) . ?
C33 C34 1.389(3) . ?
C33 O12 1.405(3) . ?
C34 C35 1.391(3) . ?
O12 C36 1.366(3) . ?
C36 O13 1.191(3) . ?
C36 C37 1.487(3) . ?
C37 C38 1.400(3) . ?
C37 C42 1.409(3) . ?
C38 C39 1.392(3) . ?
C39 C40 1.382(4) . ?
C40 C41 1.392(3) . ?
C41 C42 1.394(3) . ?
C42 O14 1.365(3) . ?
O14 C43 1.440(3) . ?
C43 C44 1.507(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 123.4(2) . . ?
O1 N1 C1 119.0(2) . . ?
O2 N1 C1 117.5(2) . . ?
C2 C1 C6 122.8(2) . . ?
C2 C1 N1 118.1(2) . . ?
C6 C1 N1 119.2(2) . . ?
C1 C2 C3 118.3(2) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 C5 122.5(2) . . ?
C3 C4 O3 118.3(2) . . ?
C5 C4 O3 119.1(2) . . ?
C6 C5 C4 118.5(2) . . ?
C7 O3 C4 117.71(17) . . ?
C5 C6 C1 118.8(2) . . ?
O4 C7 O3 122.9(2) . . ?
O4 C7 C8 126.3(2) . . ?
O3 C7 C8 110.77(18) . . ?
C9 C8 C13 119.6(2) . . ?
C9 C8 C7 118.18(19) . . ?
C13 C8 C7 122.2(2) . . ?
C8 C9 C10 120.8(2) . . ?
C11 C10 C9 118.5(2) . . ?
C10 C11 C12 121.7(2) . . ?
C10 C11 O5 121.6(2) . . ?
C12 C11 O5 116.47(19) . . ?
C13 C12 C11 119.2(2) . . ?
C12 C13 C8 120.1(2) . . ?
C14 O5 C11 118.98(18) . . ?
O6 C14 O5 122.2(2) . . ?
O6 C14 C15 124.4(2) . . ?
O5 C14 C15 113.34(19) . . ?
C16 C15 C20 119.3(2) . . ?
C16 C15 C14 115.0(2) . . ?
C20 C15 C14 125.68(19) . . ?
C17 C16 C15 121.6(2) . . ?
C16 C17 C18 118.5(2) . . ?
C19 C18 C17 121.3(2) . . ?
C18 C19 C20 120.6(2) . . ?
O7 C20 C19 123.0(2) . . ?
O7 C20 C15 118.30(19) . . ?
C19 C20 C15 118.7(2) . . ?
C20 O7 C21 119.14(18) . . ?
O7 C21 C22 112.4(2) . . ?
O9 N2 O8 123.2(2) . . ?
O9 N2 C23 118.3(2) . . ?
O8 N2 C23 118.5(2) . . ?
C28 C23 C24 122.2(2) . . ?
C28 C23 N2 118.2(2) . . ?
C24 C23 N2 119.5(2) . . ?
C25 C24 C23 118.2(2) . . ?
C26 C25 C24 119.7(2) . . ?
C25 C26 C27 121.7(2) . . ?
C25 C26 O10 116.3(2) . . ?
C27 C26 O10 121.9(2) . . ?
C28 C27 C26 118.8(2) . . ?
C23 C28 C27 119.3(2) . . ?
C29 O10 C26 118.42(17) . . ?
O11 C29 O10 123.8(2) . . ?
O11 C29 C30 124.0(2) . . ?
O10 C29 C30 112.18(19) . . ?
C31 C30 C35 120.2(2) . . ?
C31 C30 C29 116.6(2) . . ?
C35 C30 C29 123.2(2) . . ?
C32 C31 C30 120.5(2) . . ?
C31 C32 C33 118.5(2) . . ?
C32 C33 C34 122.1(2) . . ?
C32 C33 O12 118.0(2) . . ?
C34 C33 O12 119.9(2) . . ?
C33 C34 C35 119.2(2) . . ?
C34 C35 C30 119.5(2) . . ?
C36 O12 C33 115.53(17) . . ?
O13 C36 O12 122.5(2) . . ?
O13 C36 C37 126.5(2) . . ?
O12 C36 C37 110.90(18) . . ?
C38 C37 C42 119.2(2) . . ?
C38 C37 C36 120.0(2) . . ?
C42 C37 C36 120.73(19) . . ?
C39 C38 C37 120.5(2) . . ?
C40 C39 C38 119.7(2) . . ?
C39 C40 C41 120.9(2) . . ?
C40 C41 C42 119.7(2) . . ?
O14 C42 C41 123.1(2) . . ?
O14 C42 C37 116.89(19) . . ?
C41 C42 C37 120.0(2) . . ?
C42 O14 C43 117.53(19) . . ?
O14 C43 C44 105.9(2) . . ?

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
O1 N1 C1 C2 0.0(3) . . . . ?
O2 N1 C1 C2 178.8(2) . . . . ?
O1 N1 C1 C6 -179.7(2) . . . . ?
O2 N1 C1 C6 -0.8(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
N1 C1 C2 C3 -177.5(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 O3 173.76(19) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
O3 C4 C5 C6 -173.3(2) . . . . ?
C3 C4 O3 C7 108.7(2) . . . . ?
C5 C4 O3 C7 -75.7(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
N1 C1 C6 C5 177.9(2) . . . . ?
C4 O3 C7 O4 -7.8(3) . . . . ?
C4 O3 C7 C8 172.91(19) . . . . ?
O4 C7 C8 C9 -3.8(4) . . . . ?
O3 C7 C8 C9 175.4(2) . . . . ?
O4 C7 C8 C13 175.0(2) . . . . ?
O3 C7 C8 C13 -5.7(3) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 178.5(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C9 C10 C11 O5 -173.1(2) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
O5 C11 C12 C13 173.9(2) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C9 C8 C13 C12 0.9(3) . . . . ?
C7 C8 C13 C12 -178.0(2) . . . . ?
C10 C11 O5 C14 -58.6(3) . . . . ?
C12 C11 O5 C14 127.4(2) . . . . ?
C11 O5 C14 O6 -8.7(3) . . . . ?
C11 O5 C14 C15 174.36(19) . . . . ?
O6 C14 C15 C16 -13.9(3) . . . . ?
O5 C14 C15 C16 163.0(2) . . . . ?
O6 C14 C15 C20 166.2(2) . . . . ?
O5 C14 C15 C20 -16.9(3) . . . . ?
C20 C15 C16 C17 0.4(3) . . . . ?
C14 C15 C16 C17 -179.5(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 O7 -179.4(2) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C16 C15 C20 O7 178.9(2) . . . . ?
C14 C15 C20 O7 -1.2(3) . . . . ?
C16 C15 C20 C19 -0.6(3) . . . . ?
C14 C15 C20 C19 179.3(2) . . . . ?
C19 C20 O7 C21 -14.9(3) . . . . ?
C15 C20 O7 C21 165.7(2) . . . . ?
C20 O7 C21 C22 92.0(3) . . . . ?
O9 N2 C23 C28 -4.3(3) . . . . ?
O8 N2 C23 C28 176.5(2) . . . . ?
O9 N2 C23 C24 174.2(2) . . . . ?
O8 N2 C23 C24 -5.0(3) . . . . ?
C28 C23 C24 C25 2.6(4) . . . . ?
N2 C23 C24 C25 -175.8(2) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C24 C25 C26 C27 -2.4(4) . . . . ?
C24 C25 C26 O10 -179.0(2) . . . . ?
C25 C26 C27 C28 3.6(3) . . . . ?
O10 C26 C27 C28 179.9(2) . . . . ?
C24 C23 C28 C27 -1.4(4) . . . . ?
N2 C23 C28 C27 177.0(2) . . . . ?
C26 C27 C28 C23 -1.6(3) . . . . ?
C25 C26 O10 C29 -135.6(2) . . . . ?
C27 C26 O10 C29 47.9(3) . . . . ?
C26 O10 C29 O11 3.9(3) . . . . ?
C26 O10 C29 C30 -176.95(18) . . . . ?
O11 C29 C30 C31 -13.8(3) . . . . ?
O10 C29 C30 C31 167.0(2) . . . . ?
O11 C29 C30 C35 166.0(3) . . . . ?
O10 C29 C30 C35 -13.2(3) . . . . ?
C35 C30 C31 C32 -0.6(3) . . . . ?
C29 C30 C31 C32 179.3(2) . . . . ?
C30 C31 C32 C33 -0.1(3) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C31 C32 C33 O12 176.9(2) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
O12 C33 C34 C35 -176.46(19) . . . . ?
C33 C34 C35 C30 -0.6(3) . . . . ?
C31 C30 C35 C34 0.9(3) . . . . ?
C29 C30 C35 C34 -178.9(2) . . . . ?
C32 C33 O12 C36 96.3(2) . . . . ?
C34 C33 O12 C36 -87.2(3) . . . . ?
C33 O12 C36 O13 5.0(3) . . . . ?
C33 O12 C36 C37 -172.13(18) . . . . ?
O13 C36 C37 C38 -145.2(3) . . . . ?
O12 C36 C37 C38 31.8(3) . . . . ?
O13 C36 C37 C42 31.7(4) . . . . ?
O12 C36 C37 C42 -151.3(2) . . . . ?
C42 C37 C38 C39 -0.9(3) . . . . ?
C36 C37 C38 C39 176.1(2) . . . . ?
C37 C38 C39 C40 -0.6(3) . . . . ?
C38 C39 C40 C41 1.4(3) . . . . ?
C39 C40 C41 C42 -0.6(4) . . . . ?
C40 C41 C42 O14 176.5(2) . . . . ?
C40 C41 C42 C37 -0.9(3) . . . . ?
C38 C37 C42 O14 -175.9(2) . . . . ?
C36 C37 C42 O14 7.2(3) . . . . ?
C38 C37 C42 C41 1.7(3) . . . . ?
C36 C37 C42 C41 -175.3(2) . . . . ?
C41 C42 O14 C43 -7.1(3) . . . . ?
C37 C42 O14 C43 170.4(2) . . . . ?
C42 O14 C43 C44 -169.2(2) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042


_diffrn_radiation_monochromator  mirror

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1901
_database_code_depnum_ccdc_archive 'CCDC 2495787'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-O8
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 N O7'
_chemical_melting_point          ?


_exptl_crystal_description       plate

_exptl_crystal_colour            'clear intense colourless'

_diffrn_ambient_temperature      120(2)
_chemical_formula_weight         491.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_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.
;

_cell_length_a                   8.4603(2)
_cell_length_b                   19.3760(4)
_cell_length_c                   15.6361(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.724(2)
_cell_angle_gamma                90
_cell_volume                     2479.00(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120

_cell_measurement_reflns_used    18044

_cell_measurement_theta_min      1.7180

_cell_measurement_theta_max      28.9580

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.44680

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            40260
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.708
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5686
_reflns_number_gt                4645
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.5613P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5686
_refine_ls_number_parameters     485
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N -0.04863(13) 0.32769(5) 0.78775(7) 0.0333(2) Uani 1 1 d . . . . .
O1 O -0.17418(11) 0.29350(5) 0.77562(7) 0.0438(2) Uani 1 1 d . . . . .
O2 O -0.04494(13) 0.39075(5) 0.79330(8) 0.0475(3) Uani 1 1 d . . . . .
C1 C 0.10726(14) 0.29121(6) 0.79808(8) 0.0270(2) Uani 1 1 d . . . . .
C2 C 0.24186(16) 0.32684(6) 0.78683(9) 0.0326(3) Uani 1 1 d . . . . .
H1 H 0.2319(18) 0.3747(8) 0.7701(10) 0.042(4) Uiso 1 1 d . . . . .
C3 C 0.38857(16) 0.29172(6) 0.79836(9) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.484(2) 0.3146(8) 0.7898(10) 0.043(4) Uiso 1 1 d . . . . .
C4 C 0.39497(14) 0.22295(6) 0.82236(8) 0.0276(2) Uani 1 1 d . . . . .
C5 C 0.26030(15) 0.18778(6) 0.83383(9) 0.0312(3) Uani 1 1 d . . . . .
H3 H 0.2710(17) 0.1398(8) 0.8503(9) 0.033(4) Uiso 1 1 d . . . . .
C6 C 0.11289(15) 0.22212(6) 0.82061(9) 0.0303(3) Uani 1 1 d . . . . .
H4 H 0.0153(19) 0.2006(8) 0.8268(10) 0.040(4) Uiso 1 1 d . . . . .
O3 O 0.54435(10) 0.18760(4) 0.84023(6) 0.0325(2) Uani 1 1 d . . . . .
C7 C 0.58141(14) 0.15648(6) 0.76990(8) 0.0296(3) Uani 1 1 d . . . . .
O4 O 0.49858(12) 0.16333(6) 0.69595(7) 0.0489(3) Uani 1 1 d . . . . .
C8 C 0.73334(14) 0.11516(6) 0.79537(8) 0.0275(2) Uani 1 1 d . . . . .
C9 C 0.78539(15) 0.08322(6) 0.72746(9) 0.0329(3) Uani 1 1 d . . . . .
H5 H 0.7216(19) 0.0887(8) 0.6671(11) 0.045(4) Uiso 1 1 d . . . . .
C10 C 0.92945(16) 0.04555(6) 0.74646(9) 0.0334(3) Uani 1 1 d . . . . .
H6 H 0.9665(19) 0.0228(8) 0.6986(11) 0.043(4) Uiso 1 1 d . . . . .
C11 C 1.01873(14) 0.04055(6) 0.83325(9) 0.0290(3) Uani 1 1 d . . . . .
C12 C 0.96779(14) 0.07051(6) 0.90185(9) 0.0289(3) Uani 1 1 d . . . . .
H7 H 1.0327(18) 0.0663(7) 0.9626(10) 0.033(4) Uiso 1 1 d . . . . .
C13 C 0.82302(14) 0.10829(6) 0.88281(8) 0.0276(2) Uani 1 1 d . . . . .
H8 H 0.7877(17) 0.1304(7) 0.9308(9) 0.029(3) Uiso 1 1 d . . . . .
O5 O 1.17208(10) 0.00884(4) 0.84988(6) 0.0334(2) Uani 1 1 d . . . . .
C14 C 1.18565(14) -0.05614(6) 0.88663(8) 0.0264(2) Uani 1 1 d . . . . .
O6 O 1.07035(10) -0.08404(4) 0.90301(7) 0.0364(2) Uani 1 1 d . . . . .
C15 C 1.35380(14) -0.08257(6) 0.89921(8) 0.0270(2) Uani 1 1 d . . . . .
C16 C 1.47719(15) -0.03970(6) 0.88432(10) 0.0352(3) Uani 1 1 d . . . . .
H9 H 1.4502(19) 0.0091(8) 0.8668(10) 0.043(4) Uiso 1 1 d . . . . .
C17 C 1.63425(16) -0.06386(7) 0.89271(11) 0.0415(3) Uani 1 1 d . . . . .
H10 H 1.719(2) -0.0336(9) 0.8821(11) 0.052(5) Uiso 1 1 d . . . . .
C18 C 1.66953(16) -0.13202(7) 0.91603(10) 0.0383(3) Uani 1 1 d . . . . .
H11 H 1.779(2) -0.1497(8) 0.9203(11) 0.048(4) Uiso 1 1 d . . . . .
C19 C 1.55100(16) -0.17571(6) 0.93136(9) 0.0330(3) Uani 1 1 d . . . . .
H12 H 1.5815(19) -0.2218(9) 0.9487(11) 0.045(4) Uiso 1 1 d . . . . .
C20 C 1.39290(15) -0.15170(6) 0.92409(8) 0.0284(2) Uani 1 1 d D . . . .
O7 O 1.27327(11) -0.19167(4) 0.94021(7) 0.0381(2) Uani 1 1 d D . . . .
C21A C 1.3150(5) -0.2636(2) 0.9637(3) 0.0303(9) Uani 0.7 1 d D . P A 1
H13 H 1.336(3) -0.2869(10) 0.9106(12) 0.021(5) Uiso 0.7 1 d . . P B 1
H14 H 1.416(3) -0.2665(10) 1.0104(13) 0.026(5) Uiso 0.7 1 d . . P C 1
C22A C 1.1698(2) -0.29217(9) 0.99065(13) 0.0291(4) Uani 0.7 1 d D . P A 1
H15 H 1.197(3) -0.3429(11) 1.0044(14) 0.037(5) Uiso 0.7 1 d . . P D 1
H16 H 1.162(2) -0.2700(10) 1.0456(13) 0.028(5) Uiso 0.7 1 d . . P E 1
C23A C 1.0092(2) -0.28476(9) 0.92040(13) 0.0294(4) Uani 0.7 1 d D . P A 1
H17 H 0.990(3) -0.2348(11) 0.9071(14) 0.036(5) Uiso 0.7 1 d . . P F 1
H18 H 1.020(3) -0.3075(11) 0.8662(15) 0.037(5) Uiso 0.7 1 d . . P G 1
C24 C 0.86119(18) -0.31589(7) 0.95346(14) 0.0483(4) Uani 1 1 d D . . . .
H19 H 0.8500(19) -0.3030(8) 1.0052(11) 0.038(4) Uiso 1 1 d . . . . .
H20 H 0.764(2) -0.2995(8) 0.9089(11) 0.040(4) Uiso 1 1 d . . . . .
C25 C 0.8590(2) -0.39429(8) 0.95653(19) 0.0656(6) Uani 1 1 d D . . . .
H21 H 0.861(3) -0.4113(11) 0.9002(15) 0.076(7) Uiso 1 1 d . . . . .
H22 H 0.963(3) -0.4121(12) 0.9942(16) 0.093(7) Uiso 1 1 d . . . . .
C26A C 0.7168(5) -0.4242(2) 0.9887(3) 0.0373(8) Uani 0.8 1 d D . P H 1
H23 H 0.726(3) -0.4110(13) 1.0504(17) 0.065(7) Uiso 0.8 1 d . . P I 1
H24 H 0.612(2) -0.4039(9) 0.9545(12) 0.029(4) Uiso 0.8 1 d . . P J 1
C27A C 0.7048(4) -0.50260(16) 0.9818(3) 0.0486(7) Uani 0.8 1 d D . P H 1
H25 H 0.812(3) -0.5245(12) 1.0147(15) 0.056(6) Uiso 0.8 1 d . . P K 1
H26 H 0.624(3) -0.5196(13) 1.0147(17) 0.072(7) Uiso 0.8 1 d . . P L 1
C28A C 0.6509(7) -0.5281(2) 0.8869(3) 0.0698(13) Uani 0.8 1 d D . P H 1
H27 H 0.730468 -0.513512 0.854680 0.105 Uiso 0.8 1 calc R U P H 1
H28 H 0.543503 -0.508635 0.858397 0.105 Uiso 0.8 1 calc R U P H 1
H29 H 0.643825 -0.578581 0.886559 0.105 Uiso 0.8 1 calc R U P H 1
C21B C 1.2814(13) -0.2664(6) 0.9371(7) 0.038(3) Uani 0.3 1 d D . P A 2
H30 H 1.356729 -0.282927 0.992571 0.046 Uiso 0.3 1 calc R U P A 2
H31 H 1.328682 -0.279732 0.887687 0.046 Uiso 0.3 1 calc R U P A 2
C22B C 1.1166(6) -0.3031(2) 0.9252(3) 0.0354(9) Uani 0.3 1 d D . P A 2
H32 H 1.048391 -0.293080 0.864989 0.043 Uiso 0.3 1 calc R U P A 2
H33 H 1.136168 -0.353474 0.929217 0.043 Uiso 0.3 1 calc R U P A 2
C23B C 1.0222(5) -0.2832(2) 0.9911(3) 0.0348(9) Uani 0.3 1 d D . P A 2
H34 H 1.074305 -0.301676 1.050568 0.042 Uiso 0.3 1 calc R U P A 2
H35 H 1.011993 -0.232443 0.994776 0.042 Uiso 0.3 1 calc R U P A 2
C26B C 0.723(3) -0.4329(8) 0.9663(15) 0.056(6) Uani 0.2 1 d D . P H 2
H36 H 0.623279 -0.410246 0.929841 0.067 Uiso 0.2 1 calc R U P H 2
H37 H 0.718153 -0.428711 1.028737 0.067 Uiso 0.2 1 calc R U P H 2
C27B C 0.7115(17) -0.5090(5) 0.9430(9) 0.044(3) Uani 0.2 1 d D . P H 2
H38 H 0.823578 -0.528052 0.955395 0.052 Uiso 0.2 1 calc R U P H 2
H39 H 0.653909 -0.532945 0.982187 0.052 Uiso 0.2 1 calc R U P H 2
C28B C 0.625(3) -0.5249(11) 0.8489(11) 0.071(6) Uani 0.2 1 d D . P H 2
H40 H 0.623096 -0.574982 0.839830 0.106 Uiso 0.2 1 calc R U P H 2
H41 H 0.683437 -0.502912 0.809371 0.106 Uiso 0.2 1 calc R U P H 2
H42 H 0.513226 -0.507271 0.836084 0.106 Uiso 0.2 1 calc R U P H 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
N1 O2 1.2248(14) . ?
N1 O1 1.2250(14) . ?
N1 C1 1.4686(15) . ?
C1 C2 1.3806(17) . ?
C1 C6 1.3821(16) . ?
C2 C3 1.3864(18) . ?
C3 C4 1.3818(16) . ?
C4 C5 1.3778(17) . ?
C4 O3 1.4017(14) . ?
C5 C6 1.3818(17) . ?
O3 C7 1.3589(15) . ?
C7 O4 1.1973(16) . ?
C7 C8 1.4804(16) . ?
C8 C13 1.3912(17) . ?
C8 C9 1.3936(18) . ?
C9 C10 1.3865(17) . ?
C10 C11 1.3786(19) . ?
C11 C12 1.3814(18) . ?
C11 O5 1.3988(13) . ?
C12 C13 1.3927(16) . ?
O5 C14 1.3767(13) . ?
C14 O6 1.1985(14) . ?
C14 C15 1.4773(16) . ?
C15 C16 1.3991(17) . ?
C15 C20 1.4106(16) . ?
C16 C17 1.3833(18) . ?
C17 C18 1.3824(19) . ?
C18 C19 1.3790(19) . ?
C19 C20 1.3932(17) . ?
C20 O7 1.3482(14) . ?
O7 C21B 1.451(11) . ?
O7 C21A 1.461(5) . ?
C21A C22A 1.503(5) . ?
C22A C23A 1.521(2) . ?
C23A C24 1.590(3) . ?
C24 C23B 1.481(4) . ?
C24 C25 1.520(2) . ?
C25 C26B 1.415(14) . ?
C25 C26A 1.530(4) . ?
C26A C27A 1.525(5) . ?
C27A C28A 1.519(4) . ?
C21B C22B 1.534(10) . ?
C22B C23B 1.506(6) . ?
C26B C27B 1.516(14) . ?
C27B C28B 1.498(13) . ?

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
O2 N1 O1 123.77(11) . . ?
O2 N1 C1 117.80(10) . . ?
O1 N1 C1 118.42(10) . . ?
C2 C1 C6 122.73(11) . . ?
C2 C1 N1 119.48(10) . . ?
C6 C1 N1 117.78(10) . . ?
C1 C2 C3 118.57(11) . . ?
C4 C3 C2 118.72(11) . . ?
C5 C4 C3 122.39(11) . . ?
C5 C4 O3 117.77(10) . . ?
C3 C4 O3 119.76(11) . . ?
C4 C5 C6 119.16(11) . . ?
C5 C6 C1 118.41(11) . . ?
C7 O3 C4 115.93(9) . . ?
O4 C7 O3 122.25(11) . . ?
O4 C7 C8 125.08(11) . . ?
O3 C7 C8 112.67(10) . . ?
C13 C8 C9 120.49(11) . . ?
C13 C8 C7 122.37(11) . . ?
C9 C8 C7 117.13(11) . . ?
C10 C9 C8 120.09(13) . . ?
C11 C10 C9 118.67(12) . . ?
C10 C11 C12 122.26(11) . . ?
C10 C11 O5 117.65(11) . . ?
C12 C11 O5 119.87(11) . . ?
C11 C12 C13 119.07(12) . . ?
C8 C13 C12 119.39(11) . . ?
C14 O5 C11 117.02(9) . . ?
O6 C14 O5 121.05(10) . . ?
O6 C14 C15 128.59(10) . . ?
O5 C14 C15 110.36(9) . . ?
C16 C15 C20 118.49(11) . . ?
C16 C15 C14 120.41(10) . . ?
C20 C15 C14 121.08(10) . . ?
C17 C16 C15 121.51(12) . . ?
C18 C17 C16 119.09(12) . . ?
C19 C18 C17 120.96(12) . . ?
C18 C19 C20 120.42(12) . . ?
O7 C20 C19 122.94(11) . . ?
O7 C20 C15 117.55(10) . . ?
C19 C20 C15 119.51(11) . . ?
C20 O7 C21B 121.5(4) . . ?
C20 O7 C21A 116.7(2) . . ?
O7 C21A C22A 105.0(3) . . ?
C21A C22A C23A 114.0(2) . . ?
C22A C23A C24 111.22(15) . . ?
C23B C24 C25 115.6(2) . . ?
C25 C24 C23A 113.99(14) . . ?
C26B C25 C24 123.3(8) . . ?
C24 C25 C26A 113.9(2) . . ?
C27A C26A C25 113.4(3) . . ?
C28A C27A C26A 113.1(3) . . ?
O7 C21B C22B 114.6(8) . . ?
C23B C22B C21B 115.0(6) . . ?
C24 C23B C22B 102.3(3) . . ?
C25 C26B C27B 119.4(14) . . ?
C28B C27B C26B 114.9(13) . . ?

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
O2 N1 C1 C2 -19.41(17) . . . . ?
O1 N1 C1 C2 161.79(12) . . . . ?
O2 N1 C1 C6 159.35(12) . . . . ?
O1 N1 C1 C6 -19.45(17) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C2 C3 178.91(11) . . . . ?
C1 C2 C3 C4 -1.30(19) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 O3 -175.70(11) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
O3 C4 C5 C6 177.11(11) . . . . ?
C4 C5 C6 C1 -1.35(19) . . . . ?
C2 C1 C6 C5 1.13(19) . . . . ?
N1 C1 C6 C5 -177.59(11) . . . . ?
C5 C4 O3 C7 93.64(13) . . . . ?
C3 C4 O3 C7 -89.43(14) . . . . ?
C4 O3 C7 O4 5.86(17) . . . . ?
C4 O3 C7 C8 -174.87(9) . . . . ?
O4 C7 C8 C13 -178.96(13) . . . . ?
O3 C7 C8 C13 1.80(16) . . . . ?
O4 C7 C8 C9 1.61(19) . . . . ?
O3 C7 C8 C9 -177.63(10) . . . . ?
C13 C8 C9 C10 -1.48(18) . . . . ?
C7 C8 C9 C10 177.97(11) . . . . ?
C8 C9 C10 C11 0.03(18) . . . . ?
C9 C10 C11 C12 1.40(18) . . . . ?
C9 C10 C11 O5 -173.14(10) . . . . ?
C10 C11 C12 C13 -1.34(17) . . . . ?
O5 C11 C12 C13 173.08(9) . . . . ?
C9 C8 C13 C12 1.53(17) . . . . ?
C7 C8 C13 C12 -177.89(10) . . . . ?
C11 C12 C13 C8 -0.15(16) . . . . ?
C10 C11 O5 C14 -107.03(12) . . . . ?
C12 C11 O5 C14 78.30(14) . . . . ?
C11 O5 C14 O6 0.37(17) . . . . ?
C11 O5 C14 C15 179.49(10) . . . . ?
O6 C14 C15 C16 -173.59(13) . . . . ?
O5 C14 C15 C16 7.38(16) . . . . ?
O6 C14 C15 C20 8.1(2) . . . . ?
O5 C14 C15 C20 -170.93(11) . . . . ?
C20 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C17 -177.76(13) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C19 C20 O7 -178.50(12) . . . . ?
C18 C19 C20 C15 1.22(19) . . . . ?
C16 C15 C20 O7 178.43(11) . . . . ?
C14 C15 C20 O7 -3.24(17) . . . . ?
C16 C15 C20 C19 -1.31(18) . . . . ?
C14 C15 C20 C19 177.03(11) . . . . ?
C19 C20 O7 C21B -21.1(5) . . . . ?
C15 C20 O7 C21B 159.2(5) . . . . ?
C19 C20 O7 C21A -1.8(3) . . . . ?
C15 C20 O7 C21A 178.5(2) . . . . ?
C20 O7 C21A C22A 171.87(17) . . . . ?
O7 C21A C22A C23A 56.2(3) . . . . ?
C21A C22A C23A C24 -179.9(2) . . . . ?
C22A C23A C24 C25 -73.1(2) . . . . ?
C23B C24 C25 C26B 147.8(11) . . . . ?
C23A C24 C25 C26A 179.8(2) . . . . ?
C24 C25 C26A C27A 173.6(3) . . . . ?
C25 C26A C27A C28A -70.1(4) . . . . ?
C20 O7 C21B C22B -160.0(5) . . . . ?
O7 C21B C22B C23B -53.3(9) . . . . ?
C25 C24 C23B C22B 69.2(4) . . . . ?
C21B C22B C23B C24 170.0(5) . . . . ?
C24 C25 C26B C27B 162.7(12) . . . . ?
C25 C26B C27B C28B -90(2) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038


_diffrn_radiation_monochromator  mirror

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1201
_database_code_depnum_ccdc_archive 'CCDC 2495793'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-S5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O6 S'
_chemical_melting_point          ?


_exptl_crystal_description       Platelet

_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      120
_chemical_formula_weight         465.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_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.
;

_cell_length_a                   23.480(2)
_cell_length_b                   9.1320(5)
_cell_length_c                   23.543(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.234(3)
_cell_angle_gamma                90
_cell_volume                     4405.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    120

_cell_measurement_reflns_used    10048

_cell_measurement_theta_min      2.0

_cell_measurement_theta_max      25.0

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.40

_exptl_crystal_size_min          0.05

_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.930

_exptl_absorpt_correction_T_max  0.987

_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method       'profile data from φ-scans'

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            23947
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5047
_reflns_number_gt                4131
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+3.7351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5047
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.14325(10) 0.0464(2) 0.55906(9) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.08205(11) 0.2339(2) 0.51083(11) 0.0432(6) Uani 1 1 d . . . . .
N1 N 0.12403(11) 0.1446(3) 0.51789(11) 0.0302(5) Uani 1 1 d . . . . .
C1 C 0.15236(12) 0.1540(3) 0.47435(13) 0.0262(6) Uani 1 1 d . . . . .
C2 C 0.13194(14) 0.2644(3) 0.42890(14) 0.0305(6) Uani 1 1 d . . . . .
H1 H 0.0996(16) 0.335(4) 0.4245(16) 0.048(10) Uiso 1 1 d . . . . .
C3 C 0.15887(14) 0.2739(3) 0.38829(14) 0.0319(6) Uani 1 1 d . . . . .
H2 H 0.1463(16) 0.349(4) 0.3560(16) 0.045(9) Uiso 1 1 d . . . . .
C4 C 0.20576(12) 0.1725(3) 0.39547(12) 0.0257(6) Uani 1 1 d . . . . .
C5 C 0.22626(13) 0.0633(3) 0.44118(13) 0.0299(6) Uani 1 1 d . . . . .
H3 H 0.2579(15) -0.001(4) 0.4449(15) 0.039(9) Uiso 1 1 d . . . . .
C6 C 0.19957(13) 0.0525(3) 0.48205(13) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.2130(14) -0.022(4) 0.5146(15) 0.036(8) Uiso 1 1 d . . . . .
O3 O 0.23909(9) 0.1868(2) 0.35992(9) 0.0341(5) Uani 1 1 d . . . . .
C7 C 0.20618(13) 0.1590(3) 0.29453(13) 0.0265(6) Uani 1 1 d . . . . .
O4 O 0.15057(9) 0.1191(2) 0.26648(10) 0.0356(5) Uani 1 1 d . . . . .
C8 C 0.24868(12) 0.1854(3) 0.26542(12) 0.0246(6) Uani 1 1 d . . . . .
C9 C 0.22818(13) 0.1403(3) 0.20184(13) 0.0284(6) Uani 1 1 d . . . . .
H5 H 0.1863(14) 0.087(3) 0.1751(14) 0.028(7) Uiso 1 1 d . . . . .
C10 C 0.26506(14) 0.1671(3) 0.17184(14) 0.0321(6) Uani 1 1 d . . . . .
H6 H 0.2499(16) 0.138(4) 0.1273(16) 0.049(10) Uiso 1 1 d . . . . .
C11 C 0.32299(13) 0.2439(3) 0.20638(13) 0.0284(6) Uani 1 1 d . . . . .
C12 C 0.34500(14) 0.2878(3) 0.27028(13) 0.0302(6) Uani 1 1 d . . . . .
H7 H 0.3879(17) 0.338(4) 0.2920(16) 0.052(10) Uiso 1 1 d . . . . .
C13 C 0.30814(13) 0.2587(3) 0.29969(13) 0.0279(6) Uani 1 1 d . . . . .
H8 H 0.3242(14) 0.295(3) 0.3461(14) 0.030(8) Uiso 1 1 d . . . . .
O5 O 0.36417(10) 0.2921(3) 0.18292(10) 0.0413(6) Uani 1 1 d . . . . .
C14 C 0.36490(13) 0.2456(3) 0.12890(13) 0.0278(6) Uani 1 1 d . . . . .
O6 O 0.33094(12) 0.1491(3) 0.09544(12) 0.0528(7) Uani 1 1 d . . . . .
C15 C 0.41437(12) 0.3288(3) 0.12060(12) 0.0233(5) Uani 1 1 d . . . . .
C16 C 0.42646(13) 0.2955(3) 0.06848(13) 0.0258(6) Uani 1 1 d . . . . .
C17 C 0.47570(13) 0.3758(3) 0.06476(14) 0.0279(6) Uani 1 1 d . . . . .
H9 H 0.4865(13) 0.355(3) 0.0341(13) 0.023(7) Uiso 1 1 d . . . . .
C18 C 0.50969(13) 0.4841(3) 0.10905(13) 0.0284(6) Uani 1 1 d . . . . .
H10 H 0.5424(15) 0.538(3) 0.1044(14) 0.036(8) Uiso 1 1 d . . . . .
C19 C 0.49665(13) 0.5189(3) 0.15867(14) 0.0301(6) Uani 1 1 d . . . . .
H11 H 0.5191(15) 0.595(4) 0.1890(15) 0.039(9) Uiso 1 1 d . . . . .
C20 C 0.44945(13) 0.4400(3) 0.16431(13) 0.0268(6) Uani 1 1 d . . . . .
H12 H 0.4394(13) 0.465(3) 0.1967(13) 0.026(7) Uiso 1 1 d . . . . .
S1 S 0.38086(4) 0.16133(8) 0.01053(3) 0.0317(2) Uani 1 1 d . . . . .
C21 C 0.41229(15) 0.1720(3) -0.04588(14) 0.0315(6) Uani 1 1 d . . . . .
H13 H 0.4054(14) 0.276(4) -0.0641(14) 0.037(8) Uiso 1 1 d . . . . .
H14 H 0.4583(15) 0.142(3) -0.0224(14) 0.030(8) Uiso 1 1 d . . . . .
C22 C 0.37263(15) 0.0685(3) -0.10253(14) 0.0320(6) Uani 1 1 d . . . . .
H15 H 0.3806(15) -0.033(4) -0.0847(16) 0.045(9) Uiso 1 1 d . . . . .
H16 H 0.3244(16) 0.097(3) -0.1225(15) 0.039(8) Uiso 1 1 d . . . . .
C23 C 0.39378(14) 0.0788(3) -0.15502(14) 0.0314(6) Uani 1 1 d . . . . .
H17 H 0.3598(15) 0.031(4) -0.1958(15) 0.038(8) Uiso 1 1 d . . . . .
H18 H 0.3933(14) 0.188(3) -0.1689(14) 0.033(8) Uiso 1 1 d . . . . .
C24 C 0.46039(16) 0.0127(4) -0.13395(15) 0.0386(7) Uani 1 1 d . . . . .
H19 H 0.4953(15) 0.066(4) -0.0943(16) 0.041(9) Uiso 1 1 d . . . . .
H20 H 0.4605(18) -0.093(4) -0.1176(18) 0.064(11) Uiso 1 1 d . . . . .
C25 C 0.47867(19) 0.0163(4) -0.18777(18) 0.0435(8) Uani 1 1 d . . . . .
H21 H 0.4468(18) -0.035(4) -0.2265(18) 0.055(10) Uiso 1 1 d . . . . .
H22 H 0.4750(16) 0.123(4) -0.2043(16) 0.052(10) Uiso 1 1 d . . . . .
H23 H 0.5245(19) -0.026(4) -0.1714(18) 0.064(11) 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
O1 N1 1.233(3) . ?
O2 N1 1.226(3) . ?
N1 C1 1.472(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.387(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.370(4) . ?
C4 O3 1.403(3) . ?
C5 C6 1.385(4) . ?
O3 C7 1.367(3) . ?
C7 O4 1.197(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.392(4) . ?
C8 C13 1.396(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.390(4) . ?
C11 O5 1.399(3) . ?
C12 C13 1.373(4) . ?
O5 C14 1.349(3) . ?
C14 O6 1.191(3) . ?
C14 C15 1.479(3) . ?
C15 C20 1.393(4) . ?
C15 C16 1.421(3) . ?
C16 C17 1.407(4) . ?
C16 S1 1.755(3) . ?
C17 C18 1.375(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.382(4) . ?
S1 C21 1.810(3) . ?
C21 C22 1.525(4) . ?
C22 C23 1.543(4) . ?
C23 C24 1.516(4) . ?
C24 C25 1.524(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 123.5(2) . . ?
O2 N1 C1 118.3(2) . . ?
O1 N1 C1 118.2(2) . . ?
C2 C1 C6 123.0(2) . . ?
C2 C1 N1 118.7(2) . . ?
C6 C1 N1 118.3(2) . . ?
C1 C2 C3 118.7(3) . . ?
C2 C3 C4 118.6(3) . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 O3 116.9(2) . . ?
C3 C4 O3 120.5(2) . . ?
C4 C5 C6 119.5(3) . . ?
C5 C6 C1 117.8(3) . . ?
C7 O3 C4 118.8(2) . . ?
O4 C7 O3 122.8(2) . . ?
O4 C7 C8 126.5(2) . . ?
O3 C7 C8 110.7(2) . . ?
C9 C8 C13 119.1(2) . . ?
C9 C8 C7 119.5(2) . . ?
C13 C8 C7 121.4(2) . . ?
C10 C9 C8 121.6(3) . . ?
C9 C10 C11 118.1(3) . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 O5 126.7(2) . . ?
C12 C11 O5 111.9(2) . . ?
C13 C12 C11 119.8(3) . . ?
C12 C13 C8 120.0(2) . . ?
C14 O5 C11 127.1(2) . . ?
O6 C14 O5 123.0(2) . . ?
O6 C14 C15 127.5(2) . . ?
O5 C14 C15 109.6(2) . . ?
C20 C15 C16 119.9(2) . . ?
C20 C15 C14 119.8(2) . . ?
C16 C15 C14 120.3(2) . . ?
C17 C16 C15 117.3(2) . . ?
C17 C16 S1 121.5(2) . . ?
C15 C16 S1 121.16(19) . . ?
C18 C17 C16 121.2(3) . . ?
C17 C18 C19 121.4(2) . . ?
C18 C19 C20 118.7(3) . . ?
C19 C20 C15 121.5(3) . . ?
C16 S1 C21 102.72(13) . . ?
C22 C21 S1 108.35(19) . . ?
C21 C22 C23 111.4(2) . . ?
C24 C23 C22 113.4(2) . . ?
C23 C24 C25 112.6(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
O2 N1 C1 C2 1.7(4) . . . . ?
O1 N1 C1 C2 -179.1(2) . . . . ?
O2 N1 C1 C6 -179.6(2) . . . . ?
O1 N1 C1 C6 -0.4(4) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 O3 -173.5(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
O3 C4 C5 C6 173.9(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C5 C4 O3 C7 114.2(3) . . . . ?
C3 C4 O3 C7 -71.8(3) . . . . ?
C4 O3 C7 O4 -2.1(4) . . . . ?
C4 O3 C7 C8 177.8(2) . . . . ?
O4 C7 C8 C9 -10.8(4) . . . . ?
O3 C7 C8 C9 169.3(2) . . . . ?
O4 C7 C8 C13 167.2(3) . . . . ?
O3 C7 C8 C13 -12.7(4) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 2.5(5) . . . . ?
C9 C10 C11 O5 -174.4(3) . . . . ?
C10 C11 C12 C13 -1.8(5) . . . . ?
O5 C11 C12 C13 175.5(3) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 1.2(4) . . . . ?
C7 C8 C13 C12 -176.8(3) . . . . ?
C10 C11 O5 C14 -17.2(5) . . . . ?
C12 C11 O5 C14 165.7(3) . . . . ?
C11 O5 C14 O6 -3.7(5) . . . . ?
C11 O5 C14 C15 178.0(3) . . . . ?
O6 C14 C15 C20 179.3(3) . . . . ?
O5 C14 C15 C20 -2.4(3) . . . . ?
O6 C14 C15 C16 -1.0(5) . . . . ?
O5 C14 C15 C16 177.3(2) . . . . ?
C20 C15 C16 C17 1.8(4) . . . . ?
C14 C15 C16 C17 -177.9(2) . . . . ?
C20 C15 C16 S1 -177.3(2) . . . . ?
C14 C15 C16 S1 3.0(3) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
S1 C16 C17 C18 177.8(2) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C18 C19 C20 C15 -1.1(4) . . . . ?
C16 C15 C20 C19 -0.6(4) . . . . ?
C14 C15 C20 C19 179.1(2) . . . . ?
C17 C16 S1 C21 -2.5(3) . . . . ?
C15 C16 S1 C21 176.6(2) . . . . ?
C16 S1 C21 C22 -175.4(2) . . . . ?
S1 C21 C22 C23 176.4(2) . . . . ?
C21 C22 C23 C24 71.1(4) . . . . ?
C22 C23 C24 C25 176.8(3) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.059


_diffrn_radiation_monochromator  'Graphite Monochromator'

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1502_a
_database_code_depnum_ccdc_archive 'CCDC 2495796'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-O6
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O7'
_chemical_formula_weight         463.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.589(2)
_cell_length_b                   8.341(3)
_cell_length_c                   32.969(6)
_cell_angle_alpha                90.416(10)
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2361.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26127
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.853
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4519
_reflns_number_gt                2960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0012(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4519
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.2513(3) 0.2848(2) 0.60633(6) 0.0328(6) Uani 1 1 d . . . . .
O2 O 0.2676(3) 0.0993(2) 0.54015(6) 0.0315(6) Uani 1 1 d . . . . .
O3 O 0.1365(3) -0.4087(2) 0.37830(7) 0.0324(6) Uani 1 1 d . . . . .
O4 O 0.3991(3) -0.3958(3) 0.38021(9) 0.0474(7) Uani 1 1 d . . . . .
O5 O 0.2109(3) 0.2250(2) 0.48188(6) 0.0319(6) Uani 1 1 d . . . . .
C1 C 0.2498(4) -0.1960(3) 0.41562(9) 0.0263(7) Uani 1 1 d . . . . .
C2 C 0.2451(4) 0.2234(3) 0.52240(9) 0.0274(7) Uani 1 1 d . . . . .
C29 C 0.2467(4) 0.3880(3) 0.53937(9) 0.0286(7) Uani 1 1 d . . . . .
C3 C 0.3858(4) -0.1204(4) 0.42940(10) 0.0279(8) Uani 1 1 d . . . . .
H3 H 0.490(4) -0.163(4) 0.4215(10) 0.027(9) Uiso 1 1 d . . . . .
C4 C 0.2260(4) 0.0779(3) 0.46127(9) 0.0273(8) Uani 1 1 d . . . . .
C5 C 0.2542(5) 0.4148(3) 0.58152(9) 0.0299(7) Uani 1 1 d . . . . .
C6 C 0.3732(5) 0.0187(4) 0.45229(10) 0.0302(8) Uani 1 1 d . . . . .
H6 H 0.466(5) 0.073(4) 0.4631(11) 0.046(11) Uiso 1 1 d . . . . .
C7 C 0.1045(4) -0.1357(4) 0.42517(11) 0.0301(8) Uani 1 1 d . . . . .
H7 H -0.004(5) -0.194(4) 0.4173(11) 0.044(10) Uiso 1 1 d . . . . .
C8 C 0.0911(5) 0.0027(4) 0.44862(11) 0.0322(8) Uani 1 1 d . . . . .
H8 H -0.023(5) 0.051(4) 0.4550(11) 0.037(10) Uiso 1 1 d . . . . .
O6 O 0.1164(4) -0.9896(3) 0.25849(9) 0.0535(8) Uani 1 1 d . . . . .
C10 C 0.2738(5) -0.3405(4) 0.38991(10) 0.0323(8) Uani 1 1 d . . . . .
C11 C 0.2517(6) 0.3103(4) 0.64957(10) 0.0343(8) Uani 1 1 d . . . . .
N1 N 0.1574(4) -0.9892(3) 0.29419(10) 0.0379(8) Uani 1 1 d . . . . .
O7 O 0.1974(4) -1.1102(3) 0.31244(8) 0.0508(8) Uani 1 1 d . . . . .
C14 C 0.2630(5) 0.5717(4) 0.59584(11) 0.0358(9) Uani 1 1 d . . . . .
C15 C 0.2433(5) 0.5200(3) 0.51325(11) 0.0354(8) Uani 1 1 d . . . . .
C16 C 0.2602(5) 0.6997(4) 0.56920(10) 0.0385(9) Uani 1 1 d . . . . .
C17 C 0.1572(4) -0.8354(4) 0.31574(10) 0.0321(8) Uani 1 1 d . . . . .
C18 C 0.2304(5) 0.1505(4) 0.66984(11) 0.0395(9) Uani 1 1 d . . . . .
H18 H 0.127(4) 0.097(3) 0.6560(10) 0.029(9) Uiso 1 1 d . . . . .
C19 C 0.1497(4) -0.5537(4) 0.35664(10) 0.0304(8) Uani 1 1 d . . . . .
C20 C 0.0991(4) -0.5579(4) 0.31766(11) 0.0329(8) Uani 1 1 d . . . . .
H20 H 0.068(4) -0.461(4) 0.3051(10) 0.031(9) Uiso 1 1 d . . . . .
C21 C 0.2495(5) 0.6756(4) 0.52805(11) 0.0410(9) Uani 1 1 d . . . . .
C22 C 0.3648(5) 0.0345(5) 0.66332(13) 0.0417(10) Uani 1 1 d . . . . .
H22 H 0.364(5) 0.008(4) 0.6334(13) 0.061(12) Uiso 1 1 d . . . . .
C23 C 0.1016(5) -0.7016(4) 0.29649(11) 0.0366(9) Uani 1 1 d . . . . .
H23 H 0.066(4) -0.712(3) 0.2669(10) 0.025(8) Uiso 1 1 d . . . . .
C24 C 0.2106(6) -0.8317(4) 0.35499(11) 0.0418(10) Uani 1 1 d . . . . .
H24 H 0.246(5) -0.930(4) 0.3679(10) 0.048(10) Uiso 1 1 d . . . . .
C25 C 0.2059(5) -0.6885(4) 0.37587(11) 0.0428(11) Uani 1 1 d . . . . .
H25 H 0.240(4) -0.676(3) 0.4045(9) 0.031(8) Uiso 1 1 d . . . . .
C26 C 0.3154(6) -0.1345(5) 0.72789(12) 0.0482(11) Uani 1 1 d . . . . .
C27 C 0.3361(6) -0.1313(4) 0.68244(13) 0.0466(11) Uani 1 1 d . . . . .
H32 H 0.242(5) -0.173(4) 0.6709(11) 0.042(11) Uiso 1 1 d . . . . .
C28 C 0.4589(7) -0.0798(7) 0.75084(17) 0.0592(13) Uani 1 1 d . . . . .
H39 H 0.538(7) -0.153(6) 0.7430(15) 0.077(17) Uiso 1 1 d . . . . .
H1 H 0.268(4) 0.806(3) 0.5819(8) 0.025(8) Uiso 1 1 d . . . . .
H26 H 0.241(5) 0.510(3) 0.4835(10) 0.038(9) Uiso 1 1 d . . . . .
H27 H 0.236(5) 0.763(4) 0.5107(11) 0.053(11) Uiso 1 1 d . . . . .
H30 H 0.216(5) 0.172(4) 0.6987(10) 0.039(9) Uiso 1 1 d . . . . .
H28 H 0.168(5) 0.382(4) 0.6563(11) 0.038(10) Uiso 1 1 d . . . . .
H29 H 0.266(5) 0.590(4) 0.6243(11) 0.052(11) Uiso 1 1 d . . . . .
H31 H 0.463(4) 0.091(4) 0.6772(10) 0.032(9) Uiso 1 1 d . . . . .
H35 H 0.284(5) -0.247(4) 0.7330(11) 0.052(11) Uiso 1 1 d . . . . .
H33 H 0.438(5) -0.197(4) 0.6755(11) 0.047(11) Uiso 1 1 d . . . . .
H34 H 0.341(5) 0.371(4) 0.6567(10) 0.027(9) Uiso 1 1 d . . . . .
H36 H 0.450(6) -0.084(5) 0.7786(14) 0.063(14) Uiso 1 1 d . . . . .
H37 H 0.218(5) -0.070(4) 0.7385(10) 0.041(10) Uiso 1 1 d . . . . .
H38 H 0.491(6) 0.031(5) 0.7441(13) 0.062(13) 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
O1 C5 1.363(3) . ?
O1 C11 1.440(4) . ?
O2 C2 1.208(3) . ?
O3 C10 1.363(4) . ?
O3 C19 1.405(4) . ?
O4 C10 1.212(4) . ?
O5 C2 1.368(3) . ?
O5 C4 1.404(3) . ?
C1 C7 1.381(5) . ?
C1 C3 1.402(5) . ?
C1 C10 1.483(4) . ?
C2 C29 1.479(4) . ?
C29 C15 1.403(4) . ?
C29 C5 1.407(4) . ?
C3 C6 1.384(5) . ?
C4 C8 1.381(5) . ?
C4 C6 1.388(5) . ?
C5 C14 1.390(4) . ?
C7 C8 1.389(5) . ?
O6 N1 1.228(4) . ?
C11 C18 1.506(5) . ?
N1 O7 1.229(4) . ?
N1 C17 1.461(4) . ?
C14 C16 1.388(4) . ?
C15 C21 1.384(4) . ?
C16 C21 1.373(5) . ?
C17 C24 1.373(5) . ?
C17 C23 1.374(5) . ?
C18 C22 1.521(6) . ?
C19 C20 1.357(5) . ?
C19 C25 1.382(5) . ?
C20 C23 1.383(4) . ?
C22 C27 1.544(5) . ?
C24 C25 1.375(5) . ?
C26 C27 1.510(6) . ?
C26 C28 1.515(7) . ?

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
C5 O1 C11 118.8(2) . . ?
C10 O3 C19 115.4(3) . . ?
C2 O5 C4 116.0(2) . . ?
C7 C1 C3 121.1(3) . . ?
C7 C1 C10 123.3(3) . . ?
C3 C1 C10 115.5(3) . . ?
O2 C2 O5 121.5(2) . . ?
O2 C2 C29 127.7(3) . . ?
O5 C2 C29 110.8(2) . . ?
C15 C29 C5 119.2(3) . . ?
C15 C29 C2 119.9(3) . . ?
C5 C29 C2 121.0(2) . . ?
C6 C3 C1 119.0(3) . . ?
C8 C4 C6 122.7(3) . . ?
C8 C4 O5 117.5(3) . . ?
C6 C4 O5 119.7(3) . . ?
O1 C5 C14 123.2(3) . . ?
O1 C5 C29 118.1(2) . . ?
C14 C5 C29 118.7(3) . . ?
C3 C6 C4 118.9(3) . . ?
C1 C7 C8 120.1(3) . . ?
C4 C8 C7 118.2(3) . . ?
O4 C10 O3 122.4(3) . . ?
O4 C10 C1 125.5(3) . . ?
O3 C10 C1 112.1(3) . . ?
O1 C11 C18 108.3(3) . . ?
O6 N1 O7 123.6(3) . . ?
O6 N1 C17 117.5(3) . . ?
O7 N1 C17 118.9(3) . . ?
C16 C14 C5 120.7(3) . . ?
C21 C15 C29 121.4(3) . . ?
C21 C16 C14 121.2(3) . . ?
C24 C17 C23 122.6(3) . . ?
C24 C17 N1 118.1(3) . . ?
C23 C17 N1 119.2(3) . . ?
C11 C18 C22 114.2(3) . . ?
C20 C19 C25 122.1(3) . . ?
C20 C19 O3 118.1(3) . . ?
C25 C19 O3 119.7(3) . . ?
C19 C20 C23 119.3(3) . . ?
C16 C21 C15 118.7(3) . . ?
C18 C22 C27 113.1(3) . . ?
C17 C23 C20 118.4(3) . . ?
C17 C24 C25 118.4(3) . . ?
C24 C25 C19 119.2(3) . . ?
C27 C26 C28 113.1(4) . . ?
C26 C27 C22 116.5(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
C4 O5 C2 O2 -9.0(5) . . . . ?
C4 O5 C2 C29 171.9(3) . . . . ?
O2 C2 C29 C15 169.6(4) . . . . ?
O5 C2 C29 C15 -11.3(5) . . . . ?
O2 C2 C29 C5 -9.3(6) . . . . ?
O5 C2 C29 C5 169.7(3) . . . . ?
C7 C1 C3 C6 -1.2(4) . . . . ?
C10 C1 C3 C6 177.6(3) . . . . ?
C2 O5 C4 C8 109.4(3) . . . . ?
C2 O5 C4 C6 -74.4(4) . . . . ?
C11 O1 C5 C14 2.3(6) . . . . ?
C11 O1 C5 C29 -177.2(4) . . . . ?
C15 C29 C5 O1 177.4(3) . . . . ?
C2 C29 C5 O1 -3.6(6) . . . . ?
C15 C29 C5 C14 -2.0(6) . . . . ?
C2 C29 C5 C14 176.9(3) . . . . ?
C1 C3 C6 C4 0.7(5) . . . . ?
C8 C4 C6 C3 0.7(5) . . . . ?
O5 C4 C6 C3 -175.3(3) . . . . ?
C3 C1 C7 C8 0.3(5) . . . . ?
C10 C1 C7 C8 -178.4(3) . . . . ?
C6 C4 C8 C7 -1.6(5) . . . . ?
O5 C4 C8 C7 174.5(3) . . . . ?
C1 C7 C8 C4 1.0(5) . . . . ?
C19 O3 C10 O4 4.2(4) . . . . ?
C19 O3 C10 C1 -175.0(2) . . . . ?
C7 C1 C10 O4 178.6(3) . . . . ?
C3 C1 C10 O4 -0.2(5) . . . . ?
C7 C1 C10 O3 -2.3(4) . . . . ?
C3 C1 C10 O3 178.9(3) . . . . ?
C5 O1 C11 C18 173.9(3) . . . . ?
O1 C5 C14 C16 -177.7(4) . . . . ?
C29 C5 C14 C16 1.7(6) . . . . ?
C5 C29 C15 C21 1.0(6) . . . . ?
C2 C29 C15 C21 -178.0(4) . . . . ?
C5 C14 C16 C21 -0.4(7) . . . . ?
O6 N1 C17 C24 -176.6(4) . . . . ?
O7 N1 C17 C24 3.6(5) . . . . ?
O6 N1 C17 C23 4.6(5) . . . . ?
O7 N1 C17 C23 -175.2(3) . . . . ?
O1 C11 C18 C22 65.8(5) . . . . ?
C10 O3 C19 C20 -116.0(4) . . . . ?
C10 O3 C19 C25 67.2(4) . . . . ?
C25 C19 C20 C23 0.9(6) . . . . ?
O3 C19 C20 C23 -175.9(3) . . . . ?
C14 C16 C21 C15 -0.7(7) . . . . ?
C29 C15 C21 C16 0.3(6) . . . . ?
C11 C18 C22 C27 -176.9(3) . . . . ?
C24 C17 C23 C20 -0.2(6) . . . . ?
N1 C17 C23 C20 178.6(3) . . . . ?
C19 C20 C23 C17 -0.7(5) . . . . ?
C23 C17 C24 C25 0.9(6) . . . . ?
N1 C17 C24 C25 -177.9(4) . . . . ?
C17 C24 C25 C19 -0.7(7) . . . . ?
C20 C19 C25 C24 -0.2(6) . . . . ?
O3 C19 C25 C24 176.5(4) . . . . ?
C28 C26 C27 C22 -63.4(6) . . . . ?
C18 C22 C27 C26 -61.8(6) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.078



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1801
_database_code_depnum_ccdc_archive 'CCDC 2495785'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-O3
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O7'
_chemical_melting_point          ?


_exptl_crystal_description       plate

_exptl_crystal_colour            'clear intense colourless'

_diffrn_ambient_temperature      120
_chemical_formula_weight         421.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   8.1181(4)
_cell_length_b                   15.8217(4)
_cell_length_c                   16.6770(3)
_cell_angle_alpha                100.622(2)
_cell_angle_beta                 99.869(3)
_cell_angle_gamma                102.915(3)
_cell_volume                     2000.91(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120

_cell_measurement_reflns_used    17762

_cell_measurement_theta_min      2.5790

_cell_measurement_theta_max      30.5320

_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261

_exptl_crystal_size_mid          0.076

_exptl_crystal_size_min          0.048

_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.75064

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            45724
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9165
_reflns_number_gt                7191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.4429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9165
_refine_ls_number_parameters     711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C2 C -0.89408(17) -0.48000(9) 0.89477(8) 0.0260(3) Uani 1 1 d . . . . .
H1 H -0.9216(19) -0.5430(11) 0.8741(9) 0.033(4) Uiso 1 1 d . . . . .
C3 C -0.72981(17) -0.42727(9) 0.90038(8) 0.0264(3) Uani 1 1 d . . . . .
H2 H -0.642(2) -0.4525(10) 0.8828(10) 0.035(4) Uiso 1 1 d . . . . .
C5 C -0.81770(17) -0.29613(9) 0.95779(8) 0.0266(3) Uani 1 1 d . . . . .
H3 H -0.788(2) -0.2328(11) 0.9788(10) 0.037(4) Uiso 1 1 d . . . . .
C6 C -0.98198(17) -0.34898(9) 0.95274(8) 0.0273(3) Uani 1 1 d . . . . .
H4 H -1.067(2) -0.3238(10) 0.9708(10) 0.037(4) Uiso 1 1 d . . . . .
O3 O -0.53070(11) -0.28131(6) 0.93754(5) 0.0268(2) Uani 1 1 d . . . . .
C7 C -0.48313(17) -0.27369(9) 0.86401(8) 0.0287(3) Uani 1 1 d . . . . .
O4 O -0.58015(15) -0.30782(9) 0.79703(7) 0.0554(3) Uani 1 1 d . . . . .
C8 C -0.30256(16) -0.21914(8) 0.87748(8) 0.0243(3) Uani 1 1 d . . . . .
C9 C -0.23290(18) -0.21662(9) 0.80670(8) 0.0290(3) Uani 1 1 d . . . . .
H5 H -0.3029(19) -0.2489(10) 0.7530(10) 0.033(4) Uiso 1 1 d . . . . .
C10 C -0.06524(18) -0.16761(9) 0.81408(8) 0.0280(3) Uani 1 1 d . . . . .
H6 H -0.012(2) -0.1648(10) 0.7658(10) 0.036(4) Uiso 1 1 d . . . . .
H7 H 0.0316(18) -0.0861(10) 1.0172(9) 0.027(4) Uiso 1 1 d . . . . .
H8 H -0.2498(19) -0.1734(10) 1.0058(9) 0.029(4) Uiso 1 1 d . . . . .
O5 O 0.20359(11) -0.07377(6) 0.90045(6) 0.0278(2) Uani 1 1 d . . . . .
N1 N -1.19319(14) -0.49621(8) 0.91200(7) 0.0307(3) Uani 1 1 d . . . . .
O1 O -1.29991(12) -0.46074(8) 0.93740(7) 0.0421(3) Uani 1 1 d . . . . .
O2 O -1.22276(13) -0.57572(7) 0.87973(8) 0.0466(3) Uani 1 1 d . . . . .
C1 C -1.01711(15) -0.43995(8) 0.92052(8) 0.0241(3) Uani 1 1 d . . . . .
C4 C -0.69588(15) -0.33592(8) 0.93082(8) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.03093(16) -0.12032(8) 0.89266(8) 0.0234(3) Uani 1 1 d . . . . .
C12 C -0.03516(16) -0.12091(8) 0.96398(8) 0.0233(3) Uani 1 1 d . . . . .
C13 C -0.20352(16) -0.17138(8) 0.95636(8) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.22519(15) 0.00310(8) 0.87105(7) 0.0212(2) Uani 1 1 d . . . . .
O6 O 0.10782(11) 0.03637(6) 0.85634(6) 0.0264(2) Uani 1 1 d . . . . .
C15 C 0.40375(15) 0.03337(8) 0.85849(8) 0.0230(3) Uani 1 1 d . . . . .
C16 C 0.50301(17) -0.02774(10) 0.84725(10) 0.0328(3) Uani 1 1 d . . . . .
H9 H 0.457(2) -0.0884(11) 0.8534(10) 0.036(4) Uiso 1 1 d . . . . .
C17 C 0.66224(18) -0.00418(10) 0.82631(10) 0.0369(3) Uani 1 1 d . . . . .
H10 H 0.727(2) -0.0465(12) 0.8171(11) 0.053(5) Uiso 1 1 d . . . . .
C18 C 0.72334(17) 0.08135(10) 0.81639(9) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.834(2) 0.0981(10) 0.8012(10) 0.035(4) Uiso 1 1 d . . . . .
C19 C 0.62951(16) 0.14392(9) 0.82841(8) 0.0283(3) Uani 1 1 d . . . . .
H12 H 0.672(2) 0.2027(11) 0.8209(10) 0.036(4) Uiso 1 1 d . . . . .
C20 C 0.46922(15) 0.12108(8) 0.85011(8) 0.0224(3) Uani 1 1 d . . . . .
O7 O 0.37217(11) 0.17910(5) 0.86513(6) 0.0251(2) Uani 1 1 d . . . . .
C21 C 0.42450(19) 0.26608(9) 0.84790(10) 0.0320(3) Uani 1 1 d . . . . .
H13 H 0.541(2) 0.2964(11) 0.8798(10) 0.041(4) Uiso 1 1 d . . . . .
H14 H 0.424(2) 0.2576(10) 0.7867(10) 0.037(4) Uiso 1 1 d . . . . .
C22 C 0.29725(19) 0.31659(9) 0.87262(10) 0.0322(3) Uani 1 1 d . . . . .
H15 H 0.311(2) 0.3294(10) 0.9359(11) 0.039(4) Uiso 1 1 d . . . . .
H16 H 0.327(2) 0.3736(12) 0.8582(11) 0.049(5) Uiso 1 1 d . . . . .
C23 C 0.1105(2) 0.26667(11) 0.83164(11) 0.0399(4) Uani 1 1 d . . . . .
H17 H 0.026(2) 0.3005(12) 0.8458(11) 0.050(5) Uiso 1 1 d . . . . .
H18 H 0.098(2) 0.2542(12) 0.7706(13) 0.058(5) Uiso 1 1 d . . . . .
H19 H 0.081(2) 0.2078(13) 0.8486(11) 0.053(5) Uiso 1 1 d . . . . .
N2 N -1.29767(15) -0.75953(9) 0.62844(8) 0.0378(3) Uani 1 1 d . . . . .
O8 O -1.39061(14) -0.71668(9) 0.65838(9) 0.0567(3) Uani 1 1 d . . . . .
O9 O -1.34284(15) -0.84018(8) 0.59927(8) 0.0544(3) Uani 1 1 d . . . . .
C24 C -1.11986(16) -0.71126(9) 0.62817(8) 0.0279(3) Uani 1 1 d . . . . .
C25 C -1.02504(18) -0.75497(10) 0.58222(9) 0.0321(3) Uani 1 1 d . . . . .
H20 H -1.072(2) -0.8167(11) 0.5501(11) 0.043(4) Uiso 1 1 d . . . . .
C26 C -0.85769(18) -0.70935(10) 0.58235(9) 0.0311(3) Uani 1 1 d . . . . .
H21 H -0.790(2) -0.7341(10) 0.5515(10) 0.036(4) Uiso 1 1 d . . . . .
C27 C -0.79266(15) -0.62173(9) 0.62778(8) 0.0241(3) Uani 1 1 d . . . . .
C28 C -0.88840(16) -0.57837(9) 0.67432(8) 0.0266(3) Uani 1 1 d . . . . .
H22 H -0.8430(19) -0.5166(11) 0.7045(10) 0.034(4) Uiso 1 1 d . . . . .
C29 C -1.05534(17) -0.62433(9) 0.67427(9) 0.0288(3) Uani 1 1 d . . . . .
H23 H -1.1225(19) -0.5951(10) 0.7077(10) 0.032(4) Uiso 1 1 d . . . . .
O10 O -0.63076(11) -0.57749(6) 0.61786(5) 0.0280(2) Uani 1 1 d . . . . .
C30 C -0.50503(16) -0.52870(8) 0.68677(8) 0.0230(3) Uani 1 1 d . . . . .
O11 O -0.52457(12) -0.52279(7) 0.75707(6) 0.0348(2) Uani 1 1 d . . . . .
C31 C -0.34592(15) -0.48586(8) 0.66195(7) 0.0210(2) Uani 1 1 d . . . . .
C32 C -0.32179(16) -0.50651(8) 0.58040(8) 0.0225(3) Uani 1 1 d . . . . .
H24 H -0.4136(19) -0.5510(10) 0.5374(9) 0.030(4) Uiso 1 1 d . . . . .
C33 C -0.16928(16) -0.46463(8) 0.56095(8) 0.0222(3) Uani 1 1 d . . . . .
H25 H -0.1524(17) -0.4789(9) 0.5034(9) 0.024(3) Uiso 1 1 d . . . . .
C34 C -0.04149(15) -0.40299(8) 0.62364(8) 0.0216(2) Uani 1 1 d . . . . .
C35 C -0.06109(16) -0.38291(8) 0.70546(8) 0.0238(3) Uani 1 1 d . . . . .
H26 H 0.0304(19) -0.3419(10) 0.7473(9) 0.030(4) Uiso 1 1 d . . . . .
C36 C -0.21430(16) -0.42396(8) 0.72426(8) 0.0233(3) Uani 1 1 d . . . . .
H27 H -0.2325(19) -0.4090(10) 0.7803(10) 0.033(4) Uiso 1 1 d . . . . .
O12 O 0.11340(10) -0.36492(6) 0.60270(6) 0.0250(2) Uani 1 1 d . . . . .
C37 C 0.15981(15) -0.27275(8) 0.61526(7) 0.0208(2) Uani 1 1 d . . . . .
O13 O 0.06245(11) -0.22940(6) 0.63329(6) 0.0291(2) Uani 1 1 d . . . . .
C38 C 0.33779(15) -0.24036(8) 0.60340(7) 0.0204(2) Uani 1 1 d . . . . .
C39 C 0.44463(16) -0.29850(9) 0.59645(7) 0.0225(3) Uani 1 1 d . . . . .
H28 H 0.3978(18) -0.3600(10) 0.5982(9) 0.024(3) Uiso 1 1 d . . . . .
C40 C 0.61449(16) -0.26927(9) 0.58993(8) 0.0249(3) Uani 1 1 d . . . . .
H29 H 0.6867(19) -0.3113(10) 0.5860(9) 0.029(4) Uiso 1 1 d . . . . .
C41 C 0.68132(16) -0.17965(9) 0.59268(8) 0.0261(3) Uani 1 1 d . . . . .
H30 H 0.803(2) -0.1572(10) 0.5918(9) 0.032(4) Uiso 1 1 d . . . . .
C42 C 0.57961(16) -0.12043(9) 0.59919(8) 0.0260(3) Uani 1 1 d . . . . .
H31 H 0.6267(18) -0.0582(10) 0.6001(9) 0.028(4) Uiso 1 1 d . . . . .
C43 C 0.40527(15) -0.15002(8) 0.60260(7) 0.0220(3) Uani 1 1 d . . . . .
O14 O 0.29594(11) -0.09677(6) 0.60351(6) 0.0271(2) Uani 1 1 d . . . . .
C44 C 0.36312(17) -0.00426(9) 0.60265(9) 0.0280(3) Uani 1 1 d . . . . .
H32 H 0.4431(19) 0.0267(10) 0.6564(10) 0.028(4) Uiso 1 1 d . . . . .
H33 H 0.427(2) -0.0014(10) 0.5554(10) 0.036(4) Uiso 1 1 d . . . . .
C45 C 0.21057(19) 0.03482(10) 0.58650(9) 0.0320(3) Uani 1 1 d . . . . .
H34 H 0.252(2) 0.0977(11) 0.5835(10) 0.041(4) Uiso 1 1 d . . . . .
H35 H 0.138(2) 0.0006(11) 0.5314(11) 0.038(4) Uiso 1 1 d . . . . .
C46 C 0.1051(2) 0.03383(11) 0.65323(10) 0.0350(3) Uani 1 1 d . . . . .
H36 H -0.001(3) 0.0563(13) 0.6368(12) 0.060(5) Uiso 1 1 d . . . . .
H37 H 0.065(2) -0.0290(11) 0.6617(10) 0.040(4) Uiso 1 1 d . . . . .
H38 H 0.174(2) 0.0727(11) 0.7082(11) 0.045(5) 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
C2 C1 1.3832(18) . ?
C2 C3 1.3835(18) . ?
C3 C4 1.3878(18) . ?
C5 C4 1.3796(18) . ?
C5 C6 1.3863(19) . ?
C6 C1 1.3858(18) . ?
O3 C7 1.3652(16) . ?
O3 C4 1.3972(14) . ?
C7 O4 1.2023(17) . ?
C7 C8 1.4813(18) . ?
C8 C13 1.3954(18) . ?
C8 C9 1.3968(18) . ?
C9 C10 1.3801(19) . ?
C10 C11 1.3833(19) . ?
O5 C14 1.3799(15) . ?
O5 C11 1.4017(14) . ?
N1 O1 1.2250(15) . ?
N1 O2 1.2251(16) . ?
N1 C1 1.4734(16) . ?
C11 C12 1.3868(18) . ?
C12 C13 1.3918(17) . ?
C14 O6 1.1987(14) . ?
C14 C15 1.4850(16) . ?
C15 C16 1.3973(18) . ?
C15 C20 1.4125(18) . ?
C16 C17 1.385(2) . ?
C17 C18 1.384(2) . ?
C18 C19 1.384(2) . ?
C19 C20 1.3979(18) . ?
C20 O7 1.3536(15) . ?
O7 C21 1.4434(16) . ?
C21 C22 1.507(2) . ?
C22 C23 1.517(2) . ?
N2 O9 1.2248(17) . ?
N2 O8 1.2294(17) . ?
N2 C24 1.4757(17) . ?
C24 C25 1.379(2) . ?
C24 C29 1.381(2) . ?
C25 C26 1.3881(19) . ?
C26 C27 1.3867(19) . ?
C27 C28 1.3879(18) . ?
C27 O10 1.3967(15) . ?
C28 C29 1.3872(18) . ?
O10 C30 1.3700(15) . ?
C30 O11 1.1993(15) . ?
C30 C31 1.4814(17) . ?
C31 C32 1.3968(17) . ?
C31 C36 1.3990(17) . ?
C32 C33 1.3882(17) . ?
C33 C34 1.3858(17) . ?
C34 C35 1.3876(18) . ?
C34 O12 1.3983(14) . ?
C35 C36 1.3838(18) . ?
O12 C37 1.3882(15) . ?
C37 O13 1.1972(14) . ?
C37 C38 1.4810(16) . ?
C38 C39 1.4013(17) . ?
C38 C43 1.4152(17) . ?
C39 C40 1.3827(17) . ?
C40 C41 1.3894(19) . ?
C41 C42 1.3822(18) . ?
C42 C43 1.4024(17) . ?
C43 O14 1.3536(14) . ?
O14 C44 1.4469(15) . ?
C44 C45 1.5093(19) . ?
C45 C46 1.516(2) . ?

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
C1 C2 C3 118.90(12) . . ?
C2 C3 C4 118.46(12) . . ?
C4 C5 C6 118.92(12) . . ?
C1 C6 C5 118.44(12) . . ?
C7 O3 C4 116.16(10) . . ?
O4 C7 O3 122.41(12) . . ?
O4 C7 C8 125.40(12) . . ?
O3 C7 C8 112.19(11) . . ?
C13 C8 C9 120.21(12) . . ?
C13 C8 C7 122.87(12) . . ?
C9 C8 C7 116.92(11) . . ?
C10 C9 C8 120.44(12) . . ?
C9 C10 C11 118.63(12) . . ?
C14 O5 C11 115.06(9) . . ?
O1 N1 O2 124.41(12) . . ?
O1 N1 C1 118.18(11) . . ?
O2 N1 C1 117.41(11) . . ?
C2 C1 C6 122.61(12) . . ?
C2 C1 N1 118.56(11) . . ?
C6 C1 N1 118.82(11) . . ?
C5 C4 C3 122.64(12) . . ?
C5 C4 O3 117.78(11) . . ?
C3 C4 O3 119.54(11) . . ?
C10 C11 C12 122.26(12) . . ?
C10 C11 O5 118.48(11) . . ?
C12 C11 O5 119.20(11) . . ?
C11 C12 C13 118.90(12) . . ?
C12 C13 C8 119.56(12) . . ?
O6 C14 O5 121.39(11) . . ?
O6 C14 C15 127.25(11) . . ?
O5 C14 C15 111.32(10) . . ?
C16 C15 C20 119.20(11) . . ?
C16 C15 C14 119.64(11) . . ?
C20 C15 C14 120.91(11) . . ?
C17 C16 C15 121.08(13) . . ?
C18 C17 C16 119.22(13) . . ?
C17 C18 C19 121.14(13) . . ?
C18 C19 C20 120.14(13) . . ?
O7 C20 C19 123.62(11) . . ?
O7 C20 C15 117.18(10) . . ?
C19 C20 C15 119.20(11) . . ?
C20 O7 C21 118.75(10) . . ?
O7 C21 C22 107.15(11) . . ?
C21 C22 C23 112.89(12) . . ?
O9 N2 O8 124.10(13) . . ?
O9 N2 C24 117.69(13) . . ?
O8 N2 C24 118.20(13) . . ?
C25 C24 C29 122.84(12) . . ?
C25 C24 N2 118.63(12) . . ?
C29 C24 N2 118.52(12) . . ?
C24 C25 C26 118.41(13) . . ?
C27 C26 C25 119.08(13) . . ?
C26 C27 C28 122.19(12) . . ?
C26 C27 O10 115.63(11) . . ?
C28 C27 O10 121.95(11) . . ?
C29 C28 C27 118.53(12) . . ?
C24 C29 C28 118.94(13) . . ?
C30 O10 C27 119.79(10) . . ?
O11 C30 O10 123.34(11) . . ?
O11 C30 C31 125.82(11) . . ?
O10 C30 C31 110.83(10) . . ?
C32 C31 C36 119.65(11) . . ?
C32 C31 C30 122.74(11) . . ?
C36 C31 C30 117.59(11) . . ?
C33 C32 C31 120.18(11) . . ?
C34 C33 C32 119.06(11) . . ?
C33 C34 C35 121.74(11) . . ?
C33 C34 O12 117.56(11) . . ?
C35 C34 O12 120.60(11) . . ?
C36 C35 C34 118.94(11) . . ?
C35 C36 C31 120.41(12) . . ?
C37 O12 C34 116.52(9) . . ?
O13 C37 O12 121.43(11) . . ?
O13 C37 C38 127.76(11) . . ?
O12 C37 C38 110.81(10) . . ?
C39 C38 C43 119.00(11) . . ?
C39 C38 C37 120.01(11) . . ?
C43 C38 C37 120.94(10) . . ?
C40 C39 C38 121.49(12) . . ?
C39 C40 C41 118.94(12) . . ?
C42 C41 C40 121.16(12) . . ?
C41 C42 C43 120.37(12) . . ?
O14 C43 C42 123.26(11) . . ?
O14 C43 C38 117.78(10) . . ?
C42 C43 C38 118.95(11) . . ?
C43 O14 C44 118.38(9) . . ?
O14 C44 C45 107.58(11) . . ?
C44 C45 C46 114.09(12) . . ?

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 -0.74(19) . . . . ?
C4 C5 C6 C1 -0.11(19) . . . . ?
C4 O3 C7 O4 3.9(2) . . . . ?
C4 O3 C7 C8 -176.46(10) . . . . ?
O4 C7 C8 C13 171.18(15) . . . . ?
O3 C7 C8 C13 -8.46(18) . . . . ?
O4 C7 C8 C9 -8.5(2) . . . . ?
O3 C7 C8 C9 171.86(11) . . . . ?
C13 C8 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C10 -179.72(12) . . . . ?
C8 C9 C10 C11 -0.87(19) . . . . ?
C3 C2 C1 C6 -0.8(2) . . . . ?
C3 C2 C1 N1 178.20(11) . . . . ?
C5 C6 C1 C2 1.21(19) . . . . ?
C5 C6 C1 N1 -177.76(11) . . . . ?
O1 N1 C1 C2 177.70(12) . . . . ?
O2 N1 C1 C2 -2.35(18) . . . . ?
O1 N1 C1 C6 -3.28(17) . . . . ?
O2 N1 C1 C6 176.67(12) . . . . ?
C6 C5 C4 C3 -1.4(2) . . . . ?
C6 C5 C4 O3 -179.23(11) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C2 C3 C4 O3 179.63(11) . . . . ?
C7 O3 C4 C5 -113.80(13) . . . . ?
C7 O3 C4 C3 68.33(15) . . . . ?
C9 C10 C11 C12 0.31(19) . . . . ?
C9 C10 C11 O5 177.25(11) . . . . ?
C14 O5 C11 C10 73.86(14) . . . . ?
C14 O5 C11 C12 -109.10(13) . . . . ?
C10 C11 C12 C13 0.54(18) . . . . ?
O5 C11 C12 C13 -176.38(10) . . . . ?
C11 C12 C13 C8 -0.82(18) . . . . ?
C9 C8 C13 C12 0.27(18) . . . . ?
C7 C8 C13 C12 -179.40(12) . . . . ?
C11 O5 C14 O6 14.53(17) . . . . ?
C11 O5 C14 C15 -163.38(10) . . . . ?
O6 C14 C15 C16 -155.25(13) . . . . ?
O5 C14 C15 C16 22.51(17) . . . . ?
O6 C14 C15 C20 18.9(2) . . . . ?
O5 C14 C15 C20 -163.31(11) . . . . ?
C20 C15 C16 C17 -1.4(2) . . . . ?
C14 C15 C16 C17 172.86(13) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 O7 178.13(12) . . . . ?
C18 C19 C20 C15 -0.81(19) . . . . ?
C16 C15 C20 O7 -177.18(12) . . . . ?
C14 C15 C20 O7 8.61(17) . . . . ?
C16 C15 C20 C19 1.83(19) . . . . ?
C14 C15 C20 C19 -172.38(11) . . . . ?
C19 C20 O7 C21 8.13(18) . . . . ?
C15 C20 O7 C21 -172.91(11) . . . . ?
C20 O7 C21 C22 -178.37(11) . . . . ?
O7 C21 C22 C23 -53.81(17) . . . . ?
O9 N2 C24 C25 11.67(19) . . . . ?
O8 N2 C24 C25 -168.88(13) . . . . ?
O9 N2 C24 C29 -168.06(13) . . . . ?
O8 N2 C24 C29 11.38(19) . . . . ?
C29 C24 C25 C26 -0.1(2) . . . . ?
N2 C24 C25 C26 -179.83(12) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C28 1.0(2) . . . . ?
C25 C26 C27 O10 -173.59(12) . . . . ?
C26 C27 C28 C29 -0.8(2) . . . . ?
O10 C27 C28 C29 173.49(11) . . . . ?
C25 C24 C29 C28 0.4(2) . . . . ?
N2 C24 C29 C28 -179.92(12) . . . . ?
C27 C28 C29 C24 0.08(19) . . . . ?
C26 C27 O10 C30 -133.65(12) . . . . ?
C28 C27 O10 C30 51.74(16) . . . . ?
C27 O10 C30 O11 1.50(18) . . . . ?
C27 O10 C30 C31 -178.64(10) . . . . ?
O11 C30 C31 C32 169.64(13) . . . . ?
O10 C30 C31 C32 -10.21(16) . . . . ?
O11 C30 C31 C36 -8.76(19) . . . . ?
O10 C30 C31 C36 171.39(10) . . . . ?
C36 C31 C32 C33 -1.16(18) . . . . ?
C30 C31 C32 C33 -179.52(11) . . . . ?
C31 C32 C33 C34 0.60(18) . . . . ?
C32 C33 C34 C35 0.84(18) . . . . ?
C32 C33 C34 O12 177.32(10) . . . . ?
C33 C34 C35 C36 -1.69(18) . . . . ?
O12 C34 C35 C36 -178.06(11) . . . . ?
C34 C35 C36 C31 1.10(18) . . . . ?
C32 C31 C36 C35 0.29(18) . . . . ?
C30 C31 C36 C35 178.74(11) . . . . ?
C33 C34 O12 C37 121.22(12) . . . . ?
C35 C34 O12 C37 -62.26(15) . . . . ?
C34 O12 C37 O13 -8.78(16) . . . . ?
C34 O12 C37 C38 171.10(10) . . . . ?
O13 C37 C38 C39 169.07(12) . . . . ?
O12 C37 C38 C39 -10.81(15) . . . . ?
O13 C37 C38 C43 -8.13(19) . . . . ?
O12 C37 C38 C43 171.99(10) . . . . ?
C43 C38 C39 C40 0.83(18) . . . . ?
C37 C38 C39 C40 -176.42(11) . . . . ?
C38 C39 C40 C41 1.79(18) . . . . ?
C39 C40 C41 C42 -2.00(19) . . . . ?
C40 C41 C42 C43 -0.4(2) . . . . ?
C41 C42 C43 O14 -175.58(12) . . . . ?
C41 C42 C43 C38 3.07(19) . . . . ?
C39 C38 C43 O14 175.48(11) . . . . ?
C37 C38 C43 O14 -7.29(17) . . . . ?
C39 C38 C43 C42 -3.24(17) . . . . ?
C37 C38 C43 C42 173.99(11) . . . . ?
C42 C43 O14 C44 -1.30(18) . . . . ?
C38 C43 O14 C44 -179.96(11) . . . . ?
C43 O14 C44 C45 168.85(11) . . . . ?
O14 C44 C45 C46 61.85(16) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.045


_diffrn_radiation_monochromator  mirror

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar1501b
_database_code_depnum_ccdc_archive 'CCDC 2495794'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-O6
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O7'
_chemical_formula_weight         463.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.588(2)
_cell_length_b                   8.361(2)
_cell_length_c                   33.011(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.1679(10)
_cell_angle_gamma                90
_cell_volume                     2370.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29274
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4267
_reflns_number_gt                4070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1153P)²+0.8655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4267
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1822
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.2523(3) 0.2847(2) 0.39369(5) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.2678(3) 0.0994(2) 0.45986(5) 0.0272(5) Uani 1 1 d . . . . .
O3 O 0.1368(3) -0.4089(2) 0.62178(6) 0.0281(5) Uani 1 1 d . . . . .
O4 O 0.3988(3) -0.3954(3) 0.61993(8) 0.0431(6) Uani 1 1 d . . . . .
O5 O 0.2109(3) 0.2248(2) 0.51825(5) 0.0285(5) Uani 1 1 d . . . . .
C1 C 0.3851(4) -0.1198(3) 0.57091(8) 0.0252(6) Uani 1 1 d . . . . .
H1 H 0.477(4) -0.165(3) 0.5774(9) 0.016(7) Uiso 1 1 d . . . . .
C2 C 0.2450(3) 0.2230(3) 0.47747(7) 0.0230(5) Uani 1 1 d . . . . .
C3 C 0.2504(4) -0.1968(3) 0.58443(7) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.2465(4) 0.3874(3) 0.46065(7) 0.0253(6) Uani 1 1 d . . . . .
C5 C 0.1039(4) -0.1360(3) 0.57464(9) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.009(5) -0.190(4) 0.5850(10) 0.032(9) Uiso 1 1 d . . . . .
C6 C 0.2543(4) 0.4147(3) 0.41848(8) 0.0252(6) Uani 1 1 d . . . . .
C7 C 0.3729(4) 0.0185(3) 0.54764(8) 0.0257(6) Uani 1 1 d . . . . .
H7 H 0.469(5) 0.077(4) 0.5370(11) 0.036(9) Uiso 1 1 d . . . . .
C36 C 0.2261(4) 0.0779(3) 0.53874(7) 0.0243(6) Uani 1 1 d . . . . .
C8 C 0.0906(4) 0.0028(3) 0.55138(9) 0.0269(6) Uani 1 1 d . . . . .
H8 H -0.018(4) 0.051(4) 0.5447(10) 0.031(9) Uiso 1 1 d . . . . .
C9 C 0.2743(4) -0.3411(3) 0.61003(8) 0.0263(6) Uani 1 1 d . . . . .
C10 C 0.2521(4) 0.3114(3) 0.35040(8) 0.0306(6) Uani 1 1 d . . . . .
H43 H 0.167(6) 0.378(5) 0.3441(12) 0.045(11) Uiso 1 1 d . . . . .
H10 H 0.348(5) 0.371(4) 0.3430(11) 0.031(9) Uiso 1 1 d . . . . .
C11 C 0.2608(4) 0.7003(3) 0.43074(9) 0.0346(7) Uani 1 1 d . . . . .
H11 H 0.282(5) 0.811(4) 0.4210(10) 0.036(9) Uiso 1 1 d . . . . .
C12 C 0.2436(4) 0.5202(3) 0.48702(9) 0.0326(7) Uani 1 1 d . . . . .
H12 H 0.233(4) 0.505(4) 0.5155(10) 0.030(8) Uiso 1 1 d . . . . .
C13 C 0.2627(4) 0.5720(3) 0.40423(8) 0.0311(6) Uani 1 1 d . . . . .
N1 N 0.1570(3) -0.9890(3) 0.70599(8) 0.0325(6) Uani 1 1 d . . . . .
C15 C 0.2504(5) 0.6752(3) 0.47212(9) 0.0393(7) Uani 1 1 d . . . . .
H15 H 0.245(5) 0.761(4) 0.4894(11) 0.041(9) Uiso 1 1 d . . . . .
C16 C 0.2303(4) 0.1504(4) 0.33023(8) 0.0359(7) Uani 1 1 d . . . . .
H16 H 0.220(5) 0.172(4) 0.3015(11) 0.038(9) Uiso 1 1 d . . . . .
O6 O 0.1163(3) -0.9892(3) 0.74130(8) 0.0492(7) Uani 1 1 d . . . . .
C19 C 0.0997(4) -0.5567(3) 0.68266(9) 0.0298(6) Uani 1 1 d . . . . .
C20 C 0.1006(4) -0.7016(4) 0.70351(8) 0.0313(6) Uani 1 1 d . . . . .
H20 H 0.059(4) -0.710(4) 0.7318(12) 0.036(9) Uiso 1 1 d . . . . .
C21 C 0.2108(5) -0.8316(3) 0.64483(9) 0.0381(8) Uani 1 1 d . . . . .
H21 H 0.254(6) -0.929(5) 0.6324(12) 0.058(12) Uiso 1 1 d . . . . .
C22 C 0.1498(3) -0.5531(3) 0.64324(8) 0.0251(6) Uani 1 1 d . . . . .
C23 C 0.3641(5) 0.0339(4) 0.33674(10) 0.0381(8) Uani 1 1 d . . . . .
H40 H 0.368(5) 0.021(4) 0.3670(12) 0.042(10) Uiso 1 1 d . . . . .
H23 H 0.457(5) 0.088(4) 0.3254(10) 0.030(8) Uiso 1 1 d . . . . .
C24 C 0.1577(4) -0.8360(3) 0.68416(8) 0.0279(6) Uani 1 1 d . . . . .
C26 C 0.3157(5) -0.1346(4) 0.27202(10) 0.0421(8) Uani 1 1 d . . . . .
H26 H 0.221(5) -0.068(4) 0.2641(11) 0.042(10) Uiso 1 1 d . . . . .
C27 C 0.3350(5) -0.1315(4) 0.31796(11) 0.0434(8) Uani 1 1 d . . . . .
H44 H 0.424(5) -0.195(5) 0.3236(13) 0.051(11) Uiso 1 1 d . . . . .
H27 H 0.228(5) -0.178(4) 0.3290(10) 0.035(9) Uiso 1 1 d . . . . .
C28 C 0.4580(6) -0.0805(6) 0.24879(14) 0.0562(10) Uani 1 1 d . . . . .
H46 H 0.487(6) 0.034(6) 0.2548(13) 0.054(12) Uiso 1 1 d . . . . .
H42 H 0.547(6) -0.146(6) 0.2569(13) 0.057(13) Uiso 1 1 d . . . . .
H28 H 0.442(7) -0.093(6) 0.2214(16) 0.072(15) Uiso 1 1 d . . . . .
O7 O 0.1978(3) -1.1098(2) 0.68758(7) 0.0456(7) Uani 1 1 d . . . . .
C37 C 0.2074(5) -0.6881(4) 0.62413(9) 0.0394(9) Uani 1 1 d . . . . .
H37 H 0.240(4) -0.678(3) 0.5964(9) 0.022(7) Uiso 1 1 d . . . . .
H38 H 0.278(6) -0.240(5) 0.2654(12) 0.055(11) Uiso 1 1 d . . . . .
H39 H 0.277(5) 0.593(4) 0.3747(11) 0.045(10) Uiso 1 1 d . . . . .
H41 H 0.128(5) 0.099(4) 0.3409(12) 0.042(10) Uiso 1 1 d . . . . .
H45 H 0.056(4) -0.460(4) 0.6946(10) 0.032(8) 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
O1 C6 1.361(3) . ?
O1 C10 1.446(3) . ?
O2 C2 1.202(3) . ?
O3 C9 1.367(4) . ?
O3 C22 1.402(3) . ?
O4 C9 1.206(4) . ?
O5 C2 1.379(3) . ?
O5 C36 1.409(3) . ?
C1 C7 1.392(4) . ?
C1 C3 1.398(4) . ?
C2 C4 1.483(3) . ?
C3 C5 1.394(4) . ?
C3 C9 1.486(3) . ?
C4 C12 1.411(4) . ?
C4 C6 1.412(3) . ?
C5 C8 1.396(4) . ?
C6 C13 1.399(4) . ?
C7 C36 1.386(4) . ?
C36 C8 1.387(4) . ?
C10 C16 1.513(4) . ?
C11 C13 1.384(4) . ?
C11 C15 1.385(4) . ?
C12 C15 1.387(4) . ?
N1 O6 1.218(4) . ?
N1 O7 1.230(3) . ?
N1 C24 1.468(3) . ?
C16 C23 1.521(5) . ?
C19 C22 1.372(4) . ?
C19 C20 1.393(4) . ?
C20 C24 1.383(4) . ?
C21 C24 1.378(4) . ?
C21 C37 1.381(4) . ?
C22 C37 1.385(4) . ?
C23 C27 1.536(5) . ?
C26 C28 1.514(6) . ?
C26 C27 1.526(5) . ?

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
C6 O1 C10 118.1(2) . . ?
C9 O3 C22 115.6(2) . . ?
C2 O5 C36 116.07(19) . . ?
C7 C1 C3 119.9(3) . . ?
O2 C2 O5 121.2(2) . . ?
O2 C2 C4 127.9(2) . . ?
O5 C2 C4 110.9(2) . . ?
C5 C3 C1 120.3(2) . . ?
C5 C3 C9 123.4(3) . . ?
C1 C3 C9 116.3(3) . . ?
C12 C4 C6 118.8(2) . . ?
C12 C4 C2 119.9(2) . . ?
C6 C4 C2 121.3(2) . . ?
C3 C5 C8 120.2(3) . . ?
O1 C6 C13 123.3(2) . . ?
O1 C6 C4 117.6(2) . . ?
C13 C6 C4 119.1(2) . . ?
C36 C7 C1 118.8(3) . . ?
C7 C36 C8 122.5(2) . . ?
C7 C36 O5 119.8(2) . . ?
C8 C36 O5 117.5(3) . . ?
C36 C8 C5 118.3(3) . . ?
O4 C9 O3 122.2(2) . . ?
O4 C9 C3 125.5(3) . . ?
O3 C9 C3 112.3(2) . . ?
O1 C10 C16 107.3(2) . . ?
C13 C11 C15 120.4(2) . . ?
C15 C12 C4 121.0(3) . . ?
C11 C13 C6 121.0(2) . . ?
O6 N1 O7 123.7(3) . . ?
O6 N1 C24 118.2(2) . . ?
O7 N1 C24 118.1(2) . . ?
C11 C15 C12 119.6(3) . . ?
C10 C16 C23 114.5(3) . . ?
C22 C19 C20 119.1(3) . . ?
C24 C20 C19 118.7(2) . . ?
C24 C21 C37 118.9(3) . . ?
C19 C22 C37 121.8(2) . . ?
C19 C22 O3 118.2(2) . . ?
C37 C22 O3 119.9(2) . . ?
C16 C23 C27 113.4(3) . . ?
C21 C24 C20 122.2(3) . . ?
C21 C24 N1 119.2(3) . . ?
C20 C24 N1 118.6(2) . . ?
C28 C26 C27 114.4(3) . . ?
C26 C27 C23 115.7(3) . . ?
C21 C37 C22 119.3(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
C36 O5 C2 O2 8.6(4) . . . . ?
C36 O5 C2 C4 -172.0(2) . . . . ?
C7 C1 C3 C5 0.1(4) . . . . ?
C7 C1 C3 C9 -178.4(2) . . . . ?
O2 C2 C4 C12 -169.2(3) . . . . ?
O5 C2 C4 C12 11.5(4) . . . . ?
O2 C2 C4 C6 9.4(5) . . . . ?
O5 C2 C4 C6 -169.9(3) . . . . ?
C1 C3 C5 C8 -0.3(4) . . . . ?
C9 C3 C5 C8 178.1(2) . . . . ?
C10 O1 C6 C13 -2.8(5) . . . . ?
C10 O1 C6 C4 176.9(3) . . . . ?
C12 C4 C6 O1 -178.1(3) . . . . ?
C2 C4 C6 O1 3.3(5) . . . . ?
C12 C4 C6 C13 1.6(5) . . . . ?
C2 C4 C6 C13 -177.1(3) . . . . ?
C3 C1 C7 C36 0.7(4) . . . . ?
C1 C7 C36 C8 -1.4(4) . . . . ?
C1 C7 C36 O5 174.6(2) . . . . ?
C2 O5 C36 C7 74.3(3) . . . . ?
C2 O5 C36 C8 -109.5(3) . . . . ?
C7 C36 C8 C5 1.3(4) . . . . ?
O5 C36 C8 C5 -174.8(2) . . . . ?
C3 C5 C8 C36 -0.4(4) . . . . ?
C22 O3 C9 O4 -5.1(4) . . . . ?
C22 O3 C9 C3 175.0(2) . . . . ?
C5 C3 C9 O4 -178.2(3) . . . . ?
C1 C3 C9 O4 0.2(4) . . . . ?
C5 C3 C9 O3 1.7(4) . . . . ?
C1 C3 C9 O3 -179.8(2) . . . . ?
C6 O1 C10 C16 -173.4(3) . . . . ?
C6 C4 C12 C15 -0.9(5) . . . . ?
C2 C4 C12 C15 177.7(3) . . . . ?
C15 C11 C13 C6 -0.1(6) . . . . ?
O1 C6 C13 C11 178.5(3) . . . . ?
C4 C6 C13 C11 -1.1(5) . . . . ?
C13 C11 C15 C12 0.7(6) . . . . ?
C4 C12 C15 C11 -0.2(6) . . . . ?
O1 C10 C16 C23 -65.5(4) . . . . ?
C22 C19 C20 C24 2.4(5) . . . . ?
C20 C19 C22 C37 -2.7(5) . . . . ?
C20 C19 C22 O3 175.2(3) . . . . ?
C9 O3 C22 C19 115.9(3) . . . . ?
C9 O3 C22 C37 -66.1(4) . . . . ?
C10 C16 C23 C27 176.8(3) . . . . ?
C37 C21 C24 C20 0.3(5) . . . . ?
C37 C21 C24 N1 178.3(3) . . . . ?
C19 C20 C24 C21 -1.2(5) . . . . ?
C19 C20 C24 N1 -179.3(3) . . . . ?
O6 N1 C24 C21 176.8(3) . . . . ?
O7 N1 C24 C21 -3.1(4) . . . . ?
O6 N1 C24 C20 -5.1(4) . . . . ?
O7 N1 C24 C20 175.0(3) . . . . ?
C28 C26 C27 C23 62.8(5) . . . . ?
C16 C23 C27 C26 62.5(5) . . . . ?
C24 C21 C37 C22 -0.5(6) . . . . ?
C19 C22 C37 C21 1.8(5) . . . . ?
O3 C22 C37 C21 -176.1(3) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar0402
_database_code_depnum_ccdc_archive 'CCDC 2495791'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-S3
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O6 S'
_chemical_melting_point          ?


_exptl_crystal_description       Platelet

_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      120
_chemical_formula_weight         437.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'

_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.
;

_cell_length_a                   7.8443(8)
_cell_length_b                   11.2237(15)
_cell_length_c                   12.9122(16)
_cell_angle_alpha                113.520(3)
_cell_angle_beta                 91.966(2)
_cell_angle_gamma                94.9238(17)
_cell_volume                     1035.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120

_cell_measurement_reflns_used    8862

_cell_measurement_theta_min      2.0

_cell_measurement_theta_max      27.5

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.05

_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.936

_exptl_absorpt_correction_T_max  0.987

_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
Rigaku CrystalClear-SM Expert 2.0 r16
;


_diffrn_measurement_method       'profile data from φ-scans'

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            18746
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             10866
_reflns_number_gt                9772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.815
_reflns_Friedel_fraction_full    0.916

_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.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.3090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)

_refine_ls_number_reflns         10866
_refine_ls_number_parameters     692
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 2.1188(3) -0.5268(3) 0.0538(3) 0.0504(8) Uani 1 1 d . . . . .
O2 O 1.9320(4) -0.6611(3) 0.0825(2) 0.0423(6) Uani 1 1 d . . . . .
N1 N 1.9706(3) -0.5659(3) 0.0615(2) 0.0301(6) Uani 1 1 d . . . . .
C1 C 1.8328(4) -0.4935(3) 0.0428(2) 0.0225(6) Uani 1 1 d . . . . .
C2 C 1.6654(4) -0.5436(3) 0.0412(3) 0.0247(6) Uani 1 1 d . . . . .
H1 H 1.635(5) -0.623(4) 0.056(3) 0.035(10) Uiso 1 1 d . . . . .
C3 C 1.5336(4) -0.4785(3) 0.0202(3) 0.0259(6) Uani 1 1 d . . . . .
H2 H 1.421(5) -0.504(4) 0.024(3) 0.034(10) Uiso 1 1 d . . . . .
C4 C 1.5760(4) -0.3663(3) 0.0029(2) 0.0237(6) Uani 1 1 d . . . . .
C5 C 1.7435(5) -0.3157(3) 0.0062(3) 0.0310(7) Uani 1 1 d . . . . .
H3 H 1.764(5) -0.231(4) -0.005(3) 0.034(10) Uiso 1 1 d . . . . .
C6 C 1.8753(4) -0.3811(3) 0.0265(3) 0.0301(7) Uani 1 1 d . . . . .
H4 H 1.990(5) -0.349(4) 0.034(3) 0.038(11) Uiso 1 1 d . . . . .
O3 O 1.4429(3) -0.3069(2) -0.02657(19) 0.0308(5) Uani 1 1 d . . . . .
C7 C 1.3857(4) -0.2037(3) 0.0581(3) 0.0222(6) Uani 1 1 d . . . . .
O4 O 1.4419(3) -0.1652(3) 0.15493(19) 0.0332(5) Uani 1 1 d . . . . .
C8 C 1.2497(4) -0.1472(3) 0.0155(2) 0.0204(5) Uani 1 1 d . . . . .
C9 C 1.1933(4) -0.0312(3) 0.0906(2) 0.0215(6) Uani 1 1 d . . . . .
H5 H 1.243(5) 0.004(4) 0.170(3) 0.032(10) Uiso 1 1 d . . . . .
C10 C 1.0678(4) 0.0267(3) 0.0547(3) 0.0219(5) Uani 1 1 d . . . . .
H6 H 1.034(5) 0.111(4) 0.104(3) 0.024(9) Uiso 1 1 d . . . . .
C11 C 1.0010(3) -0.0336(3) -0.0568(2) 0.0207(5) Uani 1 1 d . . . . .
C12 C 1.0535(4) -0.1484(3) -0.1331(3) 0.0243(6) Uani 1 1 d . . . . .
H7 H 1.006(5) -0.187(3) -0.212(3) 0.024(9) Uiso 1 1 d . . . . .
C13 C 1.1792(4) -0.2059(3) -0.0964(3) 0.0253(6) Uani 1 1 d . . . . .
H8 H 1.223(5) -0.293(4) -0.150(3) 0.038(11) Uiso 1 1 d . . . . .
O5 O 0.8840(3) 0.0253(2) -0.10056(18) 0.0251(4) Uani 1 1 d . . . . .
C14 C 0.7296(4) 0.0466(3) -0.0569(2) 0.0202(5) Uani 1 1 d . . . . .
O6 O 0.6837(3) 0.0115(2) 0.0150(2) 0.0302(5) Uani 1 1 d . . . . .
C15 C 0.6252(4) 0.1116(3) -0.1132(2) 0.0204(5) Uani 1 1 d . . . . .
C16 C 0.4548(4) 0.1174(3) -0.0852(3) 0.0241(6) Uani 1 1 d . . . . .
H9 H 0.424(4) 0.083(3) -0.024(3) 0.022(9) Uiso 1 1 d . . . . .
C17 C 0.3389(4) 0.1722(3) -0.1317(3) 0.0304(7) Uani 1 1 d . . . . .
H10 H 0.220(5) 0.178(4) -0.110(3) 0.039(11) Uiso 1 1 d . . . . .
C18 C 0.3941(4) 0.2173(3) -0.2117(3) 0.0302(7) Uani 1 1 d . . . . .
H11 H 0.312(5) 0.258(4) -0.249(3) 0.025(9) Uiso 1 1 d . . . . .
C19 C 0.5621(4) 0.2123(3) -0.2420(3) 0.0254(6) Uani 1 1 d . . . . .
H12 H 0.592(4) 0.245(3) -0.295(3) 0.016(8) Uiso 1 1 d . . . . .
C20 C 0.6821(4) 0.1608(3) -0.1932(2) 0.0209(5) Uani 1 1 d . . . . .
S1 S 0.89714(9) 0.15673(7) -0.23168(6) 0.02468(16) Uani 1 1 d . . . . .
C21 C 0.9116(4) 0.2432(3) -0.3238(3) 0.0252(6) Uani 1 1 d . . . . .
H13 H 0.821(5) 0.207(4) -0.381(4) 0.037(11) Uiso 1 1 d . . . . .
H14 H 1.014(5) 0.216(4) -0.363(3) 0.029(9) Uiso 1 1 d . . . . .
C22 C 0.9260(5) 0.3918(3) -0.2637(3) 0.0318(7) Uani 1 1 d . . . . .
H15 H 1.020(6) 0.431(4) -0.197(4) 0.042(11) Uiso 1 1 d . . . . .
O7 O 1.9411(3) -0.4780(3) 0.4126(2) 0.0384(6) Uani 1 1 d . . . . .
O8 O 2.0402(3) -0.3018(3) 0.5561(2) 0.0404(6) Uani 1 1 d . . . . .
N2 N 1.9380(3) -0.3625(3) 0.4741(3) 0.0292(6) Uani 1 1 d . . . . .
H16 H 0.813(5) 0.420(4) -0.227(3) 0.030(10) Uiso 1 1 d . . . . .
C23 C 0.9550(5) 0.4538(4) -0.3481(4) 0.0370(8) Uani 1 1 d . . . . .
H17 H 0.965(6) 0.558(5) -0.309(4) 0.053(13) Uiso 1 1 d . . . . .
H18 H 0.859(6) 0.431(5) -0.405(4) 0.051(13) Uiso 1 1 d . . . . .
H19 H 1.068(6) 0.426(4) -0.390(4) 0.047(12) Uiso 1 1 d . . . . .
C24 C 1.8001(4) -0.2941(3) 0.4497(3) 0.0237(6) Uani 1 1 d . . . . .
C25 C 1.7868(4) -0.1663(3) 0.5221(3) 0.0250(6) Uani 1 1 d . . . . .
H20 H 1.870(5) -0.119(4) 0.587(3) 0.034(10) Uiso 1 1 d . . . . .
C26 C 1.6487(4) -0.1065(3) 0.5031(3) 0.0243(6) Uani 1 1 d . . . . .
H21 H 1.632(5) -0.020(4) 0.555(3) 0.037(11) Uiso 1 1 d . . . . .
C27 C 1.5291(4) -0.1750(3) 0.4126(3) 0.0212(6) Uani 1 1 d . . . . .
C28 C 1.5480(4) -0.3014(3) 0.3364(3) 0.0230(6) Uani 1 1 d . . . . .
H22 H 1.467(5) -0.346(4) 0.274(4) 0.039(11) Uiso 1 1 d . . . . .
C29 C 1.6855(4) -0.3624(3) 0.3566(3) 0.0241(6) Uani 1 1 d . . . . .
H23 H 1.704(4) -0.447(3) 0.314(3) 0.014(8) Uiso 1 1 d . . . . .
O9 O 1.3974(3) -0.1047(2) 0.40131(18) 0.0232(4) Uani 1 1 d . . . . .
C30 C 1.2367(4) -0.1651(3) 0.3585(3) 0.0238(6) Uani 1 1 d . . . . .
O10 O 1.1936(3) -0.2787(2) 0.3340(3) 0.0391(6) Uani 1 1 d . . . . .
C31 C 1.1208(4) -0.0709(3) 0.3492(2) 0.0207(5) Uani 1 1 d . . . . .
C32 C 1.1682(4) 0.0636(3) 0.3923(3) 0.0228(6) Uani 1 1 d . . . . .
H24 H 1.287(5) 0.104(4) 0.431(3) 0.034(10) Uiso 1 1 d . . . . .
C33 C 1.0527(4) 0.1456(3) 0.3804(3) 0.0224(6) Uani 1 1 d . . . . .
H25 H 1.082(4) 0.236(4) 0.406(3) 0.023(9) Uiso 1 1 d . . . . .
C34 C 0.8918(4) 0.0913(3) 0.3265(2) 0.0201(5) Uani 1 1 d . . . . .
C35 C 0.8427(4) -0.0416(3) 0.2821(3) 0.0232(6) Uani 1 1 d . . . . .
H26 H 0.733(5) -0.076(4) 0.241(4) 0.038(11) Uiso 1 1 d . . . . .
C36 C 0.9585(4) -0.1225(3) 0.2946(3) 0.0227(6) Uani 1 1 d . . . . .
H27 H 0.928(5) -0.223(4) 0.259(3) 0.036(10) Uiso 1 1 d . . . . .
O11 O 0.7787(3) 0.1747(2) 0.31088(18) 0.0243(4) Uani 1 1 d . . . . .
C37 C 0.6468(3) 0.2015(3) 0.3790(2) 0.0195(5) Uani 1 1 d . . . . .
O12 O 0.6305(3) 0.1632(2) 0.45360(18) 0.0271(5) Uani 1 1 d . . . . .
C38 C 0.5273(3) 0.2811(3) 0.3501(2) 0.0186(5) Uani 1 1 d . . . . .
C39 C 0.4361(3) 0.3684(3) 0.4341(2) 0.0197(5) Uani 1 1 d . . . . .
C40 C 0.3199(4) 0.4378(3) 0.4019(3) 0.0228(6) Uani 1 1 d . . . . .
H28 H 0.259(4) 0.500(3) 0.467(3) 0.022(8) Uiso 1 1 d . . . . .
C41 C 0.2919(4) 0.4170(3) 0.2889(3) 0.0228(6) Uani 1 1 d . . . . .
H29 H 0.210(4) 0.468(3) 0.272(3) 0.021(8) Uiso 1 1 d . . . . .
C42 C 0.3796(4) 0.3292(3) 0.2060(3) 0.0238(6) Uani 1 1 d . . . . .
H30 H 0.362(5) 0.311(4) 0.127(3) 0.027(9) Uiso 1 1 d . . . . .
C43 C 0.4997(4) 0.2628(3) 0.2367(2) 0.0219(6) Uani 1 1 d . . . . .
H31 H 0.563(5) 0.197(4) 0.180(3) 0.026(9) Uiso 1 1 d . . . . .
S2 S 0.46252(9) 0.38623(8) 0.57713(6) 0.02681(16) Uani 1 1 d . . . . .
C44 C 0.4154(5) 0.5518(3) 0.6574(3) 0.0293(7) Uani 1 1 d . . . . .
H32 H 0.415(6) 0.546(4) 0.726(4) 0.047(12) Uiso 1 1 d . . . . .
H33 H 0.304(4) 0.568(3) 0.639(3) 0.011(7) Uiso 1 1 d . . . . .
C45 C 0.5471(6) 0.6537(4) 0.6482(3) 0.0453(10) Uani 1 1 d . . . . .
H34 H 0.663034 0.637875 0.669008 0.054 Uiso 1 1 calc R U . . .
H35 H 0.544211 0.644532 0.568599 0.054 Uiso 1 1 calc R U . . .
C46 C 0.5152(7) 0.7906(4) 0.7233(4) 0.0575(13) Uani 1 1 d . . . . .
H36 H 0.604530 0.852754 0.716010 0.086 Uiso 1 1 calc R U . . .
H37 H 0.517545 0.800119 0.802208 0.086 Uiso 1 1 calc R U . . .
H38 H 0.402662 0.808111 0.700809 0.086 Uiso 1 1 calc R U . . .


_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
O1 N1 1.228(4) . ?
O2 N1 1.220(4) . ?
N1 C1 1.475(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.379(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.379(5) . ?
C4 O3 1.405(3) . ?
C5 C6 1.394(5) . ?
O3 C7 1.360(4) . ?
C7 O4 1.201(4) . ?
C7 C8 1.482(4) . ?
C8 C9 1.396(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.381(4) . ?
C11 O5 1.402(3) . ?
C12 C13 1.391(4) . ?
O5 C14 1.353(3) . ?
C14 O6 1.199(4) . ?
C14 C15 1.489(4) . ?
C15 C16 1.396(4) . ?
C15 C20 1.419(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.386(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.401(4) . ?
C20 S1 1.774(3) . ?
S1 C21 1.811(3) . ?
C21 C22 1.525(5) . ?
C22 C23 1.523(5) . ?
O7 N2 1.223(4) . ?
O8 N2 1.225(4) . ?
N2 C24 1.473(4) . ?
C24 C25 1.381(4) . ?
C24 C29 1.383(5) . ?
C25 C26 1.386(4) . ?
C26 C27 1.386(4) . ?
C27 C28 1.391(4) . ?
C27 O9 1.391(3) . ?
C28 C29 1.396(4) . ?
O9 C30 1.364(4) . ?
C30 O10 1.199(4) . ?
C30 C31 1.489(4) . ?
C31 C36 1.393(4) . ?
C31 C32 1.395(4) . ?
C32 C33 1.392(4) . ?
C33 C34 1.385(4) . ?
C34 C35 1.381(4) . ?
C34 O11 1.409(3) . ?
C35 C36 1.386(4) . ?
O11 C37 1.356(3) . ?
C37 O12 1.208(4) . ?
C37 C38 1.484(4) . ?
C38 C43 1.401(4) . ?
C38 C39 1.405(4) . ?
C39 C40 1.402(4) . ?
C39 S2 1.779(3) . ?
C40 C41 1.389(4) . ?
C41 C42 1.385(4) . ?
C42 C43 1.390(4) . ?
S2 C44 1.809(3) . ?
C44 C45 1.519(5) . ?
C45 C46 1.502(6) . ?

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
O2 N1 O1 123.7(3) . . ?
O2 N1 C1 118.8(3) . . ?
O1 N1 C1 117.5(3) . . ?
C6 C1 C2 122.9(3) . . ?
C6 C1 N1 119.3(3) . . ?
C2 C1 N1 117.8(3) . . ?
C1 C2 C3 118.5(3) . . ?
C4 C3 C2 118.7(3) . . ?
C5 C4 C3 122.6(3) . . ?
C5 C4 O3 119.0(3) . . ?
C3 C4 O3 118.3(3) . . ?
C4 C5 C6 118.8(3) . . ?
C1 C6 C5 118.6(3) . . ?
C7 O3 C4 117.2(2) . . ?
O4 C7 O3 122.5(3) . . ?
O4 C7 C8 125.6(3) . . ?
O3 C7 C8 111.9(2) . . ?
C9 C8 C13 120.0(3) . . ?
C9 C8 C7 118.1(3) . . ?
C13 C8 C7 121.9(3) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 118.2(3) . . ?
C12 C11 C10 122.8(3) . . ?
C12 C11 O5 116.1(3) . . ?
C10 C11 O5 120.9(3) . . ?
C11 C12 C13 118.6(3) . . ?
C12 C13 C8 119.9(3) . . ?
C14 O5 C11 119.6(2) . . ?
O6 C14 O5 122.8(3) . . ?
O6 C14 C15 125.6(3) . . ?
O5 C14 C15 111.6(2) . . ?
C16 C15 C20 119.6(3) . . ?
C16 C15 C14 114.4(3) . . ?
C20 C15 C14 126.0(3) . . ?
C17 C16 C15 122.0(3) . . ?
C16 C17 C18 118.2(3) . . ?
C17 C18 C19 121.3(3) . . ?
C18 C19 C20 121.1(3) . . ?
C19 C20 C15 117.8(3) . . ?
C19 C20 S1 120.6(2) . . ?
C15 C20 S1 121.7(2) . . ?
C20 S1 C21 105.17(14) . . ?
C22 C21 S1 115.2(2) . . ?
C23 C22 C21 110.4(3) . . ?
O7 N2 O8 123.7(3) . . ?
O7 N2 C24 117.9(3) . . ?
O8 N2 C24 118.4(3) . . ?
C25 C24 C29 122.5(3) . . ?
C25 C24 N2 119.1(3) . . ?
C29 C24 N2 118.4(3) . . ?
C24 C25 C26 118.4(3) . . ?
C27 C26 C25 119.8(3) . . ?
C26 C27 C28 121.5(3) . . ?
C26 C27 O9 114.7(3) . . ?
C28 C27 O9 123.7(3) . . ?
C27 C28 C29 118.6(3) . . ?
C24 C29 C28 119.0(3) . . ?
C30 O9 C27 121.1(2) . . ?
O10 C30 O9 124.4(3) . . ?
O10 C30 C31 124.4(3) . . ?
O9 C30 C31 111.2(2) . . ?
C36 C31 C32 119.9(3) . . ?
C36 C31 C30 117.1(3) . . ?
C32 C31 C30 123.0(3) . . ?
C33 C32 C31 119.7(3) . . ?
C34 C33 C32 118.9(3) . . ?
C35 C34 C33 122.4(3) . . ?
C35 C34 O11 119.2(3) . . ?
C33 C34 O11 118.3(3) . . ?
C34 C35 C36 118.3(3) . . ?
C35 C36 C31 120.8(3) . . ?
C37 O11 C34 116.2(2) . . ?
O12 C37 O11 122.9(2) . . ?
O12 C37 C38 124.9(3) . . ?
O11 C37 C38 112.2(2) . . ?
C43 C38 C39 120.4(2) . . ?
C43 C38 C37 119.0(2) . . ?
C39 C38 C37 120.5(2) . . ?
C40 C39 C38 118.4(3) . . ?
C40 C39 S2 120.8(2) . . ?
C38 C39 S2 120.7(2) . . ?
C41 C40 C39 120.5(3) . . ?
C42 C41 C40 121.0(3) . . ?
C41 C42 C43 119.4(3) . . ?
C42 C43 C38 120.3(3) . . ?
C39 S2 C44 103.44(15) . . ?
C45 C44 S2 112.9(3) . . ?
C46 C45 C44 112.3(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
O2 N1 C1 C6 175.7(3) . . . . ?
O1 N1 C1 C6 -5.0(4) . . . . ?
O2 N1 C1 C2 -5.0(4) . . . . ?
O1 N1 C1 C2 174.3(3) . . . . ?
C6 C1 C2 C3 1.1(5) . . . . ?
N1 C1 C2 C3 -178.1(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 O3 175.3(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
O3 C4 C5 C6 -174.9(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
N1 C1 C6 C5 178.5(3) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C5 C4 O3 C7 -85.8(4) . . . . ?
C3 C4 O3 C7 98.4(3) . . . . ?
C4 O3 C7 O4 -1.7(5) . . . . ?
C4 O3 C7 C8 178.1(3) . . . . ?
O4 C7 C8 C9 7.3(5) . . . . ?
O3 C7 C8 C9 -172.6(3) . . . . ?
O4 C7 C8 C13 -173.3(3) . . . . ?
O3 C7 C8 C13 6.9(4) . . . . ?
C13 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 O5 -174.9(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
O5 C11 C12 C13 175.2(3) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C7 C8 C13 C12 -179.1(3) . . . . ?
C12 C11 O5 C14 121.5(3) . . . . ?
C10 C11 O5 C14 -63.0(4) . . . . ?
C11 O5 C14 O6 -3.7(4) . . . . ?
C11 O5 C14 C15 179.1(2) . . . . ?
O6 C14 C15 C16 -6.9(4) . . . . ?
O5 C14 C15 C16 170.2(3) . . . . ?
O6 C14 C15 C20 175.8(3) . . . . ?
O5 C14 C15 C20 -7.1(4) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?
C14 C15 C16 C17 -178.7(3) . . . . ?
C15 C16 C17 C18 2.6(5) . . . . ?
C16 C17 C18 C19 -2.2(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C15 1.2(5) . . . . ?
C18 C19 C20 S1 -179.3(3) . . . . ?
C16 C15 C20 C19 -0.7(4) . . . . ?
C14 C15 C20 C19 176.4(3) . . . . ?
C16 C15 C20 S1 179.7(2) . . . . ?
C14 C15 C20 S1 -3.1(4) . . . . ?
C19 C20 S1 C21 5.7(3) . . . . ?
C15 C20 S1 C21 -174.7(2) . . . . ?
C20 S1 C21 C22 77.5(3) . . . . ?
S1 C21 C22 C23 174.4(2) . . . . ?
O7 N2 C24 C25 175.8(3) . . . . ?
O8 N2 C24 C25 -2.4(4) . . . . ?
O7 N2 C24 C29 -2.3(4) . . . . ?
O8 N2 C24 C29 179.5(3) . . . . ?
C29 C24 C25 C26 2.9(5) . . . . ?
N2 C24 C25 C26 -175.0(3) . . . . ?
C24 C25 C26 C27 -0.5(4) . . . . ?
C25 C26 C27 C28 -3.0(5) . . . . ?
C25 C26 C27 O9 -179.3(3) . . . . ?
C26 C27 C28 C29 4.1(4) . . . . ?
O9 C27 C28 C29 -180.0(3) . . . . ?
C25 C24 C29 C28 -1.9(5) . . . . ?
N2 C24 C29 C28 176.1(3) . . . . ?
C27 C28 C29 C24 -1.7(4) . . . . ?
C26 C27 O9 C30 -148.2(3) . . . . ?
C28 C27 O9 C30 35.6(4) . . . . ?
C27 O9 C30 O10 4.4(5) . . . . ?
C27 O9 C30 C31 -177.1(2) . . . . ?
O10 C30 C31 C36 -8.8(5) . . . . ?
O9 C30 C31 C36 172.7(2) . . . . ?
O10 C30 C31 C32 171.2(3) . . . . ?
O9 C30 C31 C32 -7.2(4) . . . . ?
C36 C31 C32 C33 0.1(4) . . . . ?
C30 C31 C32 C33 -179.9(3) . . . . ?
C31 C32 C33 C34 0.5(4) . . . . ?
C32 C33 C34 C35 -1.2(4) . . . . ?
C32 C33 C34 O11 -177.4(3) . . . . ?
C33 C34 C35 C36 1.4(4) . . . . ?
O11 C34 C35 C36 177.5(3) . . . . ?
C34 C35 C36 C31 -0.8(4) . . . . ?
C32 C31 C36 C35 0.1(4) . . . . ?
C30 C31 C36 C35 -179.9(3) . . . . ?
C35 C34 O11 C37 77.8(3) . . . . ?
C33 C34 O11 C37 -105.9(3) . . . . ?
C34 O11 C37 O12 4.2(4) . . . . ?
C34 O11 C37 C38 -175.4(2) . . . . ?
O12 C37 C38 C43 -146.1(3) . . . . ?
O11 C37 C38 C43 33.5(4) . . . . ?
O12 C37 C38 C39 30.6(4) . . . . ?
O11 C37 C38 C39 -149.9(3) . . . . ?
C43 C38 C39 C40 -1.1(4) . . . . ?
C37 C38 C39 C40 -177.6(3) . . . . ?
C43 C38 C39 S2 176.9(2) . . . . ?
C37 C38 C39 S2 0.3(4) . . . . ?
C38 C39 C40 C41 2.1(4) . . . . ?
S2 C39 C40 C41 -175.9(2) . . . . ?
C39 C40 C41 C42 -0.9(5) . . . . ?
C40 C41 C42 C43 -1.3(5) . . . . ?
C41 C42 C43 C38 2.3(4) . . . . ?
C39 C38 C43 C42 -1.1(4) . . . . ?
C37 C38 C43 C42 175.5(3) . . . . ?
C40 C39 S2 C44 -29.7(3) . . . . ?
C38 C39 S2 C44 152.4(2) . . . . ?
C39 S2 C44 C45 -66.7(3) . . . . ?
S2 C44 C45 C46 -174.9(3) . . . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054


_diffrn_radiation_monochromator  'Graphite Monochromator'

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
####################################################################### 
# 
# 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_ar0801b
_database_code_depnum_ccdc_archive 'CCDC 2495792'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2025-10-16 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            o-S2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O6 S'
_chemical_melting_point          ?


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      120(2)
_chemical_formula_weight         423.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'

_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.
;

_cell_length_a                   7.9323(12)
_cell_length_b                   10.5119(15)
_cell_length_c                   12.763(2)
_cell_angle_alpha                68.561(5)
_cell_angle_beta                 89.498(8)
_cell_angle_gamma                83.654(8)
_cell_volume                     983.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120

_cell_measurement_reflns_used    7528

_cell_measurement_theta_min      1.7

_cell_measurement_theta_max      25.0

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.927

_exptl_absorpt_correction_T_max  0.959

_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method       'profile data from φ-scans'

_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            17782
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             10360
_reflns_number_gt                9061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.821
_reflns_Friedel_fraction_full    0.919

_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.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SIR2019 (Burla, Caliandro et al., 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+0.6393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)

_refine_ls_number_reflns         10360
_refine_ls_number_parameters     635
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O -1.1855(5) -0.7398(4) 0.4981(3) 0.0434(8) Uani 1 1 d . . . . .
O2 O -1.1058(4) -0.9109(4) 0.6510(3) 0.0392(8) Uani 1 1 d . . . . .
N1 N -1.0962(5) -0.7937(4) 0.5839(3) 0.0309(8) Uani 1 1 d . . . . .
C1 C -0.9690(5) -0.7149(4) 0.6074(4) 0.0274(8) Uani 1 1 d . . . . .
H1 H -0.887(6) -0.867(5) 0.752(4) 0.027(12) Uiso 1 1 d . . . . .
C2 C -0.8678(5) -0.7764(4) 0.7043(4) 0.0262(8) Uani 1 1 d . . . . .
C3 C -0.7401(5) -0.7072(4) 0.7246(3) 0.0258(8) Uani 1 1 d . . . . .
H2 H -0.665(7) -0.750(6) 0.790(5) 0.034(14) Uiso 1 1 d . . . . .
C4 C -0.7168(5) -0.5783(4) 0.6453(3) 0.0246(7) Uani 1 1 d . . . . .
C5 C -0.8235(5) -0.5145(4) 0.5510(4) 0.0282(8) Uani 1 1 d . . . . .
H3 H -0.813(8) -0.424(7) 0.505(6) 0.050(17) Uiso 1 1 d . . . . .
C6 C -0.9536(6) -0.5831(5) 0.5320(4) 0.0299(8) Uani 1 1 d . . . . .
H4 H -1.028(7) -0.534(6) 0.466(5) 0.041(15) Uiso 1 1 d . . . . .
O3 O -0.5888(4) -0.5035(3) 0.6598(3) 0.0275(6) Uani 1 1 d . . . . .
C7 C -0.4301(5) -0.5697(4) 0.6916(4) 0.0279(8) Uani 1 1 d . . . . .
O4 O -0.3895(4) -0.6880(3) 0.7021(3) 0.0414(8) Uani 1 1 d . . . . .
C8 C -0.3108(5) -0.4797(4) 0.7107(3) 0.0242(7) Uani 1 1 d . . . . .
C9 C -0.1592(5) -0.5443(4) 0.7692(4) 0.0267(8) Uani 1 1 d . . . . .
H5 H -0.147(6) -0.652(5) 0.802(4) 0.027(12) Uiso 1 1 d . . . . .
C10 C -0.0391(5) -0.4685(4) 0.7884(4) 0.0263(8) Uani 1 1 d . . . . .
H6 H 0.074(8) -0.510(7) 0.836(6) 0.055(18) Uiso 1 1 d . . . . .
C11 C -0.0753(5) -0.3267(4) 0.7468(3) 0.0243(7) Uani 1 1 d . . . . .
C12 C -0.2241(6) -0.2590(4) 0.6882(4) 0.0288(8) Uani 1 1 d . . . . .
H7 H -0.251(6) -0.148(5) 0.660(4) 0.024(12) Uiso 1 1 d . . . . .
C13 C -0.3447(5) -0.3366(4) 0.6694(4) 0.0273(8) Uani 1 1 d . . . . .
H8 H -0.460(7) -0.290(6) 0.619(5) 0.042(15) Uiso 1 1 d . . . . .
O5 O 0.0442(4) -0.2499(3) 0.7708(3) 0.0290(6) Uani 1 1 d . . . . .
C14 C 0.1571(5) -0.1999(4) 0.6887(3) 0.0243(7) Uani 1 1 d . . . . .
O6 O 0.1507(4) -0.2124(3) 0.5992(3) 0.0338(7) Uani 1 1 d . . . . .
C15 C 0.2867(5) -0.1322(4) 0.7249(3) 0.0225(7) Uani 1 1 d . . . . .
C16 C 0.3344(5) -0.1759(4) 0.8389(3) 0.0255(8) Uani 1 1 d . . . . .
H9 H 0.276(5) -0.240(4) 0.889(3) 0.004(8) Uiso 1 1 d . . . . .
C17 C 0.4627(5) -0.1169(4) 0.8727(4) 0.0276(8) Uani 1 1 d . . . . .
H10 H 0.486(7) -0.146(6) 0.946(5) 0.030(13) Uiso 1 1 d . . . . .
C18 C 0.5412(5) -0.0161(4) 0.7935(4) 0.0268(8) Uani 1 1 d . . . . .
H11 H 0.633(7) 0.022(6) 0.818(5) 0.037(14) Uiso 1 1 d . . . . .
C19 C 0.4944(5) 0.0292(4) 0.6797(4) 0.0249(7) Uani 1 1 d . . . . .
H12 H 0.551(8) 0.108(6) 0.616(5) 0.044(15) Uiso 1 1 d . . . . .
C20 C 0.3655(5) -0.0267(4) 0.6435(3) 0.0236(7) Uani 1 1 d . . . . .
S1 S 0.29712(13) 0.03592(11) 0.50038(8) 0.0306(2) Uani 1 1 d . . . . .
C21 C 0.3684(5) 0.2050(4) 0.4459(3) 0.0282(8) Uani 1 1 d . . . . .
H13 H 0.351881 0.249757 0.501923 0.034 Uiso 1 1 calc R U . . .
H14 H 0.490541 0.197650 0.429550 0.034 Uiso 1 1 calc R U . . .
C22 C 0.2644(7) 0.2888(6) 0.3388(4) 0.0404(11) Uani 1 1 d . . . . .
H15 H 0.278426 0.241760 0.285092 0.061 Uiso 1 1 calc R U . . .
H16 H 0.303240 0.380001 0.305595 0.061 Uiso 1 1 calc R U . . .
H17 H 0.144332 0.298610 0.356545 0.061 Uiso 1 1 calc R U . . .
O7 O -1.2905(5) -0.9257(5) 1.0064(4) 0.0527(10) Uani 1 1 d . . . . .
O8 O -1.1200(5) -1.0888(4) 0.9879(4) 0.0465(9) Uani 1 1 d . . . . .
N2 N -1.1485(5) -0.9808(4) 1.0037(3) 0.0322(8) Uani 1 1 d . . . . .
C23 C -1.0047(5) -0.9135(4) 1.0198(3) 0.0236(7) Uani 1 1 d . . . . .
C24 C -0.8420(5) -0.9736(4) 1.0150(4) 0.0268(8) Uani 1 1 d . . . . .
H18 H -0.822(7) -1.066(6) 1.003(5) 0.037(14) Uiso 1 1 d . . . . .
C25 C -0.7056(5) -0.9125(4) 1.0346(4) 0.0274(8) Uani 1 1 d . . . . .
H19 H -0.601(8) -0.947(6) 1.027(5) 0.036(14) Uiso 1 1 d . . . . .
C26 C -0.7362(5) -0.7940(4) 1.0565(3) 0.0251(8) Uani 1 1 d . . . . .
C27 C -0.8987(6) -0.7321(5) 1.0599(4) 0.0327(9) Uani 1 1 d . . . . .
H20 H -0.917(7) -0.641(6) 1.068(5) 0.042(15) Uiso 1 1 d . . . . .
C28 C -1.0358(5) -0.7934(5) 1.0407(4) 0.0302(8) Uani 1 1 d . . . . .
H21 H -1.149(7) -0.755(6) 1.042(5) 0.039(15) Uiso 1 1 d . . . . .
O9 O -0.5985(4) -0.7401(3) 1.0873(3) 0.0293(6) Uani 1 1 d . . . . .
C29 C -0.5496(5) -0.6233(4) 1.0096(3) 0.0238(7) Uani 1 1 d . . . . .
O10 O -0.6077(4) -0.5740(4) 0.9151(3) 0.0355(7) Uani 1 1 d . . . . .
C30 C -0.4182(5) -0.5692(4) 1.0581(3) 0.0215(7) Uani 1 1 d . . . . .
C31 C -0.3655(5) -0.6283(4) 1.1718(3) 0.0256(8) Uani 1 1 d . . . . .
H22 H -0.415(8) -0.715(6) 1.220(5) 0.050(17) Uiso 1 1 d . . . . .
C32 C -0.2453(5) -0.5720(4) 1.2146(4) 0.0271(8) Uani 1 1 d . . . . .
H23 H -0.208(6) -0.615(5) 1.295(4) 0.025(12) Uiso 1 1 d . . . . .
C33 C -0.1790(5) -0.4569(4) 1.1424(3) 0.0242(7) Uani 1 1 d . . . . .
C34 C -0.2265(5) -0.3961(4) 1.0286(3) 0.0266(8) Uani 1 1 d . . . . .
H24 H -0.190(7) -0.303(5) 0.979(4) 0.032(13) Uiso 1 1 d . . . . .
C35 C -0.3471(5) -0.4537(4) 0.9877(3) 0.0249(7) Uani 1 1 d . . . . .
H25 H -0.398(7) -0.421(6) 0.909(5) 0.040(15) Uiso 1 1 d . . . . .
O11 O -0.0686(4) -0.3978(3) 1.1915(3) 0.0305(6) Uani 1 1 d . . . . .
C36 C 0.0879(5) -0.3777(4) 1.1491(3) 0.0251(7) Uani 1 1 d . . . . .
O12 O 0.1421(4) -0.4199(3) 1.0781(3) 0.0326(7) Uani 1 1 d . . . . .
C37 C 0.1872(5) -0.3054(4) 1.2042(4) 0.0261(8) Uani 1 1 d . . . . .
C38 C 0.1207(6) -0.2343(5) 1.2740(4) 0.0309(9) Uani 1 1 d . . . . .
C39 C 0.2346(7) -0.1757(5) 1.3205(4) 0.0399(11) Uani 1 1 d . . . . .
H26 H 0.205(8) -0.117(7) 1.366(6) 0.055(18) Uiso 1 1 d . . . . .
C40 C 0.4064(7) -0.1827(6) 1.2965(5) 0.0495(14) Uani 1 1 d . . . . .
H27 H 0.480706 -0.139593 1.327365 0.059 Uiso 1 1 calc R U . . .
C41 C 0.4703(7) -0.2521(6) 1.2279(6) 0.0477(13) Uani 1 1 d . . . . .
H28 H 0.583(11) -0.250(9) 1.211(7) 0.08(3) Uiso 1 1 d . . . . .
C42 C 0.3604(6) -0.3118(5) 1.1824(4) 0.0343(9) Uani 1 1 d . . . . .
H29 H 0.394(6) -0.370(5) 1.133(4) 0.027(12) Uiso 1 1 d . . . . .
S2 S -0.09754(16) -0.22049(17) 1.30341(11) 0.0497(4) Uani 1 1 d . . . . .
C43 C -0.1268(11) -0.1225(8) 1.3904(6) 0.094(3) Uani 1 1 d D . . . .
H30 H -0.226850 -0.149655 1.436807 0.113 Uiso 1 1 calc R U . . .
H31 H -0.026512 -0.145019 1.442281 0.113 Uiso 1 1 calc R U . . .
C44 C -0.152(2) 0.0294(8) 1.3273(9) 0.161(7) Uani 1 1 d D . . . .
H32 H -0.041934 0.065747 1.318971 0.241 Uiso 1 1 calc R U . . .
H33 H -0.226986 0.073130 1.368881 0.241 Uiso 1 1 calc R U . . .
H34 H -0.203135 0.048880 1.252680 0.241 Uiso 1 1 calc R U . . .


_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
O1 N1 1.222(5) . ?
O2 N1 1.227(5) . ?
N1 C1 1.471(5) . ?
C1 C2 1.383(6) . ?
C1 C6 1.386(6) . ?
C2 C3 1.388(6) . ?
C3 C4 1.394(6) . ?
C4 C5 1.384(6) . ?
C4 O3 1.404(4) . ?
C5 C6 1.393(6) . ?
O3 C7 1.357(5) . ?
C7 O4 1.207(5) . ?
C7 C8 1.491(5) . ?
C8 C9 1.389(6) . ?
C8 C13 1.396(6) . ?
C9 C10 1.385(6) . ?
C10 C11 1.384(6) . ?
C11 C12 1.378(6) . ?
C11 O5 1.414(5) . ?
C12 C13 1.399(6) . ?
O5 C14 1.365(5) . ?
C14 O6 1.198(5) . ?
C14 C15 1.479(5) . ?
C15 C16 1.399(5) . ?
C15 C20 1.414(5) . ?
C16 C17 1.396(6) . ?
C17 C18 1.373(6) . ?
C18 C19 1.393(6) . ?
C19 C20 1.394(5) . ?
C20 S1 1.767(4) . ?
S1 C21 1.809(4) . ?
C21 C22 1.518(6) . ?
O7 N2 1.215(5) . ?
O8 N2 1.221(5) . ?
N2 C23 1.460(5) . ?
C23 C28 1.379(6) . ?
C23 C24 1.384(6) . ?
C24 C25 1.386(6) . ?
C25 C26 1.369(6) . ?
C26 C27 1.386(6) . ?
C26 O9 1.406(5) . ?
C27 C28 1.391(6) . ?
O9 C29 1.360(5) . ?
C29 O10 1.198(5) . ?
C29 C30 1.480(5) . ?
C30 C35 1.395(5) . ?
C30 C31 1.400(5) . ?
C31 C32 1.389(5) . ?
C32 C33 1.381(6) . ?
C33 C34 1.392(6) . ?
C33 O11 1.400(4) . ?
C34 C35 1.386(5) . ?
O11 C36 1.357(5) . ?
C36 O12 1.204(5) . ?
C36 C37 1.492(5) . ?
C37 C42 1.398(6) . ?
C37 C38 1.422(6) . ?
C38 C39 1.396(6) . ?
C38 S2 1.770(5) . ?
C39 C40 1.394(9) . ?
C40 C41 1.390(9) . ?
C41 C42 1.374(6) . ?
S2 C43 1.769(6) . ?
C43 C44 1.493(6) . ?

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
O1 N1 O2 123.3(4) . . ?
O1 N1 C1 118.4(4) . . ?
O2 N1 C1 118.2(4) . . ?
C2 C1 C6 122.3(4) . . ?
C2 C1 N1 118.3(4) . . ?
C6 C1 N1 119.4(4) . . ?
C1 C2 C3 119.2(4) . . ?
C2 C3 C4 118.6(4) . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 O3 116.4(3) . . ?
C3 C4 O3 121.6(3) . . ?
C4 C5 C6 119.2(4) . . ?
C1 C6 C5 118.5(4) . . ?
C7 O3 C4 118.6(3) . . ?
O4 C7 O3 123.8(4) . . ?
O4 C7 C8 123.7(4) . . ?
O3 C7 C8 112.5(3) . . ?
C9 C8 C13 120.5(4) . . ?
C9 C8 C7 117.0(3) . . ?
C13 C8 C7 122.5(4) . . ?
C10 C9 C8 120.9(4) . . ?
C11 C10 C9 117.7(4) . . ?
C12 C11 C10 123.1(4) . . ?
C12 C11 O5 119.3(4) . . ?
C10 C11 O5 117.5(4) . . ?
C11 C12 C13 118.8(4) . . ?
C8 C13 C12 119.0(4) . . ?
C14 O5 C11 115.5(3) . . ?
O6 C14 O5 122.9(3) . . ?
O6 C14 C15 125.2(4) . . ?
O5 C14 C15 111.8(3) . . ?
C16 C15 C20 120.4(3) . . ?
C16 C15 C14 119.8(3) . . ?
C20 C15 C14 119.7(3) . . ?
C17 C16 C15 119.9(4) . . ?
C18 C17 C16 119.7(4) . . ?
C17 C18 C19 121.1(4) . . ?
C18 C19 C20 120.6(4) . . ?
C19 C20 C15 118.3(3) . . ?
C19 C20 S1 121.1(3) . . ?
C15 C20 S1 120.6(3) . . ?
C20 S1 C21 102.78(19) . . ?
C22 C21 S1 107.6(3) . . ?
O7 N2 O8 123.5(4) . . ?
O7 N2 C23 118.0(4) . . ?
O8 N2 C23 118.5(4) . . ?
C28 C23 C24 122.4(4) . . ?
C28 C23 N2 118.9(4) . . ?
C24 C23 N2 118.7(4) . . ?
C23 C24 C25 118.7(4) . . ?
C26 C25 C24 119.1(4) . . ?
C25 C26 C27 122.6(4) . . ?
C25 C26 O9 118.7(4) . . ?
C27 C26 O9 118.3(4) . . ?
C26 C27 C28 118.5(4) . . ?
C23 C28 C27 118.8(4) . . ?
C29 O9 C26 116.9(3) . . ?
O10 C29 O9 122.9(3) . . ?
O10 C29 C30 126.2(4) . . ?
O9 C29 C30 110.9(3) . . ?
C35 C30 C31 119.2(3) . . ?
C35 C30 C29 118.4(3) . . ?
C31 C30 C29 122.4(3) . . ?
C32 C31 C30 120.6(4) . . ?
C33 C32 C31 118.4(4) . . ?
C32 C33 C34 122.8(3) . . ?
C32 C33 O11 116.1(3) . . ?
C34 C33 O11 121.0(3) . . ?
C35 C34 C33 117.9(4) . . ?
C34 C35 C30 121.2(4) . . ?
C36 O11 C33 118.7(3) . . ?
O12 C36 O11 122.8(4) . . ?
O12 C36 C37 124.1(4) . . ?
O11 C36 C37 112.9(3) . . ?
C42 C37 C38 119.9(4) . . ?
C42 C37 C36 114.3(4) . . ?
C38 C37 C36 125.8(4) . . ?
C39 C38 C37 117.6(4) . . ?
C39 C38 S2 120.3(4) . . ?
C37 C38 S2 122.2(3) . . ?
C40 C39 C38 121.2(5) . . ?
C41 C40 C39 120.8(4) . . ?
C42 C41 C40 118.8(5) . . ?
C41 C42 C37 121.7(5) . . ?
C43 S2 C38 107.7(3) . . ?
C44 C43 S2 114.1(6) . . ?

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
O1 N1 C1 C2 -179.8(4) . . . . ?
O2 N1 C1 C2 -0.5(6) . . . . ?
O1 N1 C1 C6 -0.3(6) . . . . ?
O2 N1 C1 C6 179.0(4) . . . . ?
C6 C1 C2 C3 -3.4(6) . . . . ?
N1 C1 C2 C3 176.1(4) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 4.0(6) . . . . ?
C2 C3 C4 O3 -179.2(4) . . . . ?
C3 C4 C5 C6 -2.8(6) . . . . ?
O3 C4 C5 C6 -179.8(4) . . . . ?
C2 C1 C6 C5 4.6(7) . . . . ?
N1 C1 C6 C5 -174.9(4) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C5 C4 O3 C7 -136.5(4) . . . . ?
C3 C4 O3 C7 46.5(5) . . . . ?
C4 O3 C7 O4 4.4(6) . . . . ?
C4 O3 C7 C8 -176.3(3) . . . . ?
O4 C7 C8 C9 -16.1(6) . . . . ?
O3 C7 C8 C9 164.6(4) . . . . ?
O4 C7 C8 C13 161.9(4) . . . . ?
O3 C7 C8 C13 -17.4(6) . . . . ?
C13 C8 C9 C10 0.4(6) . . . . ?
C7 C8 C9 C10 178.4(4) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C9 C10 C11 O5 177.3(4) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
O5 C11 C12 C13 -177.2(4) . . . . ?
C9 C8 C13 C12 -0.3(6) . . . . ?
C7 C8 C13 C12 -178.2(4) . . . . ?
C11 C12 C13 C8 0.1(6) . . . . ?
C12 C11 O5 C14 -86.6(5) . . . . ?
C10 C11 O5 C14 96.2(4) . . . . ?
C11 O5 C14 O6 4.3(6) . . . . ?
C11 O5 C14 C15 -174.8(3) . . . . ?
O6 C14 C15 C16 -149.8(4) . . . . ?
O5 C14 C15 C16 29.3(5) . . . . ?
O6 C14 C15 C20 28.2(6) . . . . ?
O5 C14 C15 C20 -152.8(4) . . . . ?
C20 C15 C16 C17 -1.1(6) . . . . ?
C14 C15 C16 C17 176.8(4) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C15 -1.4(6) . . . . ?
C18 C19 C20 S1 176.6(3) . . . . ?
C16 C15 C20 C19 1.8(6) . . . . ?
C14 C15 C20 C19 -176.1(3) . . . . ?
C16 C15 C20 S1 -176.2(3) . . . . ?
C14 C15 C20 S1 5.8(5) . . . . ?
C19 C20 S1 C21 -20.4(4) . . . . ?
C15 C20 S1 C21 157.5(3) . . . . ?
C20 S1 C21 C22 -159.4(3) . . . . ?
O7 N2 C23 C28 1.9(6) . . . . ?
O8 N2 C23 C28 -178.2(4) . . . . ?
O7 N2 C23 C24 -178.9(4) . . . . ?
O8 N2 C23 C24 0.9(6) . . . . ?
C28 C23 C24 C25 1.5(6) . . . . ?
N2 C23 C24 C25 -177.6(4) . . . . ?
C23 C24 C25 C26 -0.8(6) . . . . ?
C24 C25 C26 C27 0.0(7) . . . . ?
C24 C25 C26 O9 173.7(4) . . . . ?
C25 C26 C27 C28 0.2(7) . . . . ?
O9 C26 C27 C28 -173.5(4) . . . . ?
C24 C23 C28 C27 -1.3(7) . . . . ?
N2 C23 C28 C27 177.8(4) . . . . ?
C26 C27 C28 C23 0.4(7) . . . . ?
C25 C26 O9 C29 108.0(4) . . . . ?
C27 C26 O9 C29 -78.0(5) . . . . ?
C26 O9 C29 O10 -7.1(6) . . . . ?
C26 O9 C29 C30 173.1(3) . . . . ?
O10 C29 C30 C35 -3.3(6) . . . . ?
O9 C29 C30 C35 176.5(3) . . . . ?
O10 C29 C30 C31 175.6(4) . . . . ?
O9 C29 C30 C31 -4.5(5) . . . . ?
C35 C30 C31 C32 0.7(6) . . . . ?
C29 C30 C31 C32 -178.2(4) . . . . ?
C30 C31 C32 C33 -0.2(6) . . . . ?
C31 C32 C33 C34 -0.6(6) . . . . ?
C31 C32 C33 O11 175.1(4) . . . . ?
C32 C33 C34 C35 0.8(6) . . . . ?
O11 C33 C34 C35 -174.7(4) . . . . ?
C33 C34 C35 C30 -0.3(6) . . . . ?
C31 C30 C35 C34 -0.5(6) . . . . ?
C29 C30 C35 C34 178.5(4) . . . . ?
C32 C33 O11 C36 126.0(4) . . . . ?
C34 C33 O11 C36 -58.2(5) . . . . ?
C33 O11 C36 O12 -7.2(6) . . . . ?
C33 O11 C36 C37 176.0(3) . . . . ?
O12 C36 C37 C42 -11.2(6) . . . . ?
O11 C36 C37 C42 165.5(4) . . . . ?
O12 C36 C37 C38 168.9(4) . . . . ?
O11 C36 C37 C38 -14.3(6) . . . . ?
C42 C37 C38 C39 -1.5(6) . . . . ?
C36 C37 C38 C39 178.4(4) . . . . ?
C42 C37 C38 S2 179.2(4) . . . . ?
C36 C37 C38 S2 -0.9(6) . . . . ?
C37 C38 C39 C40 2.1(7) . . . . ?
S2 C38 C39 C40 -178.6(4) . . . . ?
C38 C39 C40 C41 -2.0(9) . . . . ?
C39 C40 C41 C42 1.1(9) . . . . ?
C40 C41 C42 C37 -0.5(9) . . . . ?
C38 C37 C42 C41 0.7(7) . . . . ?
C36 C37 C42 C41 -179.1(5) . . . . ?
C39 C38 S2 C43 1.7(5) . . . . ?
C37 C38 S2 C43 -179.0(4) . . . . ?
C38 S2 C43 C44 85.6(9) . . . . ?

_refine_diff_density_max         1.019
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.069


_diffrn_radiation_monochromator  'Graphite Monochromator'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       'Liquid crystal'
