# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_omr003_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2353953'
loop_
_audit_author_name
_audit_author_address
'Shogo Morisako'
;Sagami Chemical Research Institute
Japan
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O8, C10 H8'
_chemical_formula_sum            'C30 H28 N2 O8'
_chemical_formula_weight         544.54
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H28 N2 O8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.55420(10)
_cell_length_b                   7.02420(10)
_cell_length_c                   24.7028(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.9480(10)
_cell_angle_gamma                90
_cell_volume                     1301.16(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8730
_cell_measurement_theta_min      3.6060
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19042
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.906
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00  35.00   0.50    2.00    --    0.00 -32.00-166.00  254
  2  ω    -30.00 140.00   0.50    2.00    --   57.86  32.00  -6.00  340
  3  ω   -177.00 -23.00   0.50    2.00    -- -106.00 -32.00-166.00  308
  4  ω     28.00 178.00   0.50    2.00    --  115.73  32.00  -6.00  300
  5  ω    -33.00  83.00   0.50    2.00    --    0.00  32.00  -6.00  232
  6  ω     -1.00  58.00   0.50    2.00    --    0.00 -99.00-180.00  118
  7  ω    -86.00 -13.00   0.50    2.00    --  -57.86 125.00   0.00  146
  8  ω    -14.00  25.00   0.50    2.00    --  -57.86  15.00-180.00   78
  9  ω    -30.00  25.00   0.50    2.00    --  -57.86  30.00 120.00  110
 10  ω   -143.00 -73.00   0.50    2.00    --  -57.86-125.00 -90.00  140
 11  ω    -34.00  35.00   0.50    2.00    --   57.86 -32.00-166.00  138
 12  ω      1.00  31.00   0.50    2.00    --   57.86  95.00  40.23   60
 13  ω      1.00  31.00   0.50    2.00    --   57.86  95.00 -98.66   60
 14  ω      0.00  27.00   0.50    2.00    --   57.86  98.00   0.64   54
 15  ω      0.00  27.00   0.50    2.00    --   57.86  98.00 173.04   54
 16  ω      1.00  28.00   0.50    2.00    --   57.86  97.00 106.20   54
 17  ω     10.00 140.00   0.50    2.00    --   57.86  77.00  60.00  260
 18  ω      1.00  28.00   0.50    2.00    --   57.86  97.00 -36.49   54
 19  ω    -29.00  51.00   0.50    2.00    --   57.86 -45.00  60.00  160
 20  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 150.00  238
 21  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  63.83  236
 22  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 120.00  238
 23  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  90.00  238
 24  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -76.00  96.31  236
 25  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 129.81  238
 26  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  60.00  238
 27  ω   -177.00 -61.00   0.50    2.00    -- -106.00 -72.00  68.99  232
 28  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  44.95  236
 29  ω    -55.00 -23.00   0.50    2.00    -- -106.00  50.00   0.00   64
 30  ω   -177.00 -62.00   0.50    2.00    -- -106.00 -68.00 129.19  230
 31  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 108.06  238
 32  ω   -177.00 -34.00   0.50    2.00    -- -106.00 -37.00  90.00  286
 33  ω    -55.00 -23.00   0.50    2.00    -- -106.00  50.00-180.00   64
 34  ω     27.00 108.00   0.50    2.00    --  115.73-111.00  60.00  162
 35  ω     42.00 178.00   0.50    2.00    --  115.73  37.00  60.00  272
 36  ω     74.00 178.00   0.50    2.00    --  115.73  63.00  60.00  208
 37  ω     19.00 164.00   0.50    2.00    --  115.73   0.00-180.00  290
 38  ω     44.00  85.00   0.50    2.00    --  115.73  37.00  60.00   82
 39  ω    129.00 168.00   0.50    2.00    --  115.73  77.00  30.00   78
 40  ω     76.00 106.00   0.50    2.00    --  115.73  77.00  30.00   60
 41  ω     31.00  56.00   0.50    2.00    --  115.73 -50.00   0.00   50
 42  ω     82.00 108.00   0.50    2.00    --  115.73-111.00-180.00   52
 43  ω    112.00 157.00   0.50    2.00    --  115.73 111.00-120.00   90
 44  ω     39.00  78.00   0.50    2.00    --  115.73 -63.00  60.00   78
 45  ω     40.00  66.00   0.50    2.00    --  115.73-111.00-180.00   52
 46  ω     30.00  78.00   0.50    2.00    --  115.73 -63.00 -60.00   96
 47  ω     31.00  57.00   0.50    2.00    --  115.73 -50.00  30.00   52
 48  ω     78.00 143.00   0.50    2.00    --  115.73  77.00  90.00  130
 49  ω    107.00 174.00   0.50    2.00    --  115.73   0.00 -90.00  134
 50  ω    140.00 178.00   0.50    2.00    --  115.73  77.00 120.00   76
 51  ω     82.00 125.00   0.50    2.00    --  115.73  77.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0974066000
_diffrn_orient_matrix_UB_12      -0.0053931000
_diffrn_orient_matrix_UB_13      0.0585352000
_diffrn_orient_matrix_UB_21      0.1661009000
_diffrn_orient_matrix_UB_22      0.0894564000
_diffrn_orient_matrix_UB_23      -0.0202927000
_diffrn_orient_matrix_UB_31      -0.0716694000
_diffrn_orient_matrix_UB_32      0.2000193000
_diffrn_orient_matrix_UB_33      0.0106621000
_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4953
_reflns_number_total             5020
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0701
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53828(15) 0.49483(19) 0.81645(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O 1.09200(15) 0.34992(18) 0.90331(4) 0.0220(3) Uani 1 1 d . . . . .
O3 O 1.36723(14) 0.27046(18) 0.68571(4) 0.0218(3) Uani 1 1 d . . . . .
O4 O 0.81656(15) 0.42585(19) 0.59864(4) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.92986(16) 0.48132(18) 1.00600(5) 0.0224(3) Uani 1 1 d . . . . .
O6 O 0.84678(17) 0.71771(19) 0.94814(5) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.923360 0.779046 0.968626 0.039 Uiso 1 1 calc R U . . .
O7 O 1.00960(17) 0.25447(17) 0.49352(5) 0.0222(3) Uani 1 1 d . . . . .
O8 O 1.13530(17) 0.05822(17) 0.55797(5) 0.0233(3) Uani 1 1 d . . . . .
H8 H 1.084935 -0.024943 0.537049 0.035 Uiso 1 1 calc R U . . .
N1 N 0.79653(17) 0.4169(2) 0.87218(5) 0.0174(3) Uani 1 1 d . . . . .
N2 N 1.11216(17) 0.3683(2) 0.62946(5) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.7764(2) 0.4275(2) 0.72352(6) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.660668 0.455116 0.705722 0.021 Uiso 1 1 calc R U . . .
C2 C 0.81540(19) 0.4184(2) 0.77984(6) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.9844(2) 0.3753(2) 0.80611(6) 0.0160(3) Uani 1 1 d . . . . .
C4 C 1.1292(2) 0.3391(2) 0.77794(6) 0.0162(3) Uani 1 1 d . . . . .
H4 H 1.244779 0.310332 0.795697 0.019 Uiso 1 1 calc R U . . .
C5 C 1.0906(2) 0.3486(2) 0.72163(6) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.9218(2) 0.3924(2) 0.69556(6) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.6936(2) 0.4501(2) 0.82215(6) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.9753(2) 0.3761(2) 0.86620(6) 0.0170(3) Uani 1 1 d . . . . .
C9 C 1.2139(2) 0.3219(2) 0.67909(6) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.9326(2) 0.3996(2) 0.63606(6) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.7224(2) 0.4181(2) 0.92445(6) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.604264 0.483945 0.918518 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8459(2) 0.5386(2) 0.96445(6) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.6899(2) 0.2153(3) 0.94410(6) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.806617 0.146566 0.949478 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6096(3) 0.2149(3) 0.99835(7) 0.0295(4) Uani 1 1 d . . . . .
H14A H 0.679286 0.299324 1.024372 0.044 Uiso 1 1 calc R U . . .
H14B H 0.612218 0.085263 1.013088 0.044 Uiso 1 1 calc R U . . .
H14C H 0.485955 0.259847 0.992185 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5638(2) 0.1078(3) 0.90150(7) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.445915 0.167857 0.897882 0.037 Uiso 1 1 calc R U . . .
H15B H 0.553675 -0.024838 0.913032 0.037 Uiso 1 1 calc R U . . .
H15C H 0.611247 0.111528 0.866295 0.037 Uiso 1 1 calc R U . . .
C16 C 1.1650(2) 0.3922(2) 0.57454(6) 0.0167(3) Uani 1 1 d . . . . .
H16 H 1.102000 0.508725 0.559011 0.020 Uiso 1 1 calc R U . . .
C17 C 1.0949(2) 0.2280(2) 0.53802(6) 0.0168(3) Uani 1 1 d . . . . .
C18 C 1.36554(19) 0.4287(2) 0.57295(6) 0.0176(3) Uani 1 1 d . . . . .
H18 H 1.435902 0.322137 0.591796 0.021 Uiso 1 1 calc R U . . .
C19 C 1.4046(2) 0.4401(3) 0.51346(7) 0.0227(3) Uani 1 1 d . . . . .
H19A H 1.368861 0.320722 0.494725 0.034 Uiso 1 1 calc R U . . .
H19B H 1.532464 0.461024 0.512562 0.034 Uiso 1 1 calc R U . . .
H19C H 1.337335 0.545987 0.495112 0.034 Uiso 1 1 calc R U . . .
C20 C 1.4180(2) 0.6158(3) 0.60207(7) 0.0204(3) Uani 1 1 d . . . . .
H20A H 1.349684 0.720522 0.583483 0.031 Uiso 1 1 calc R U . . .
H20B H 1.545685 0.638659 0.601462 0.031 Uiso 1 1 calc R U . . .
H20C H 1.392150 0.608328 0.639945 0.031 Uiso 1 1 calc R U . . .
C21 C -0.0649(3) 0.8894(3) 0.82108(7) 0.0269(4) Uani 1 1 d . . . . .
H21 H -0.158806 0.905854 0.842988 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1040(3) 0.8588(3) 0.84549(7) 0.0315(4) Uani 1 1 d . . . . .
H22 H 0.127001 0.855659 0.884151 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2449(3) 0.8318(3) 0.81384(8) 0.0320(4) Uani 1 1 d . . . . .
H23 H 0.362434 0.810855 0.831251 0.038 Uiso 1 1 calc R U . . .
C24 C 0.2134(2) 0.8355(3) 0.75800(8) 0.0274(4) Uani 1 1 d . . . . .
H24 H 0.309158 0.815194 0.737030 0.033 Uiso 1 1 calc R U . . .
C25 C 0.0025(2) 0.8770(3) 0.67356(7) 0.0262(4) Uani 1 1 d . . . . .
H25 H 0.096232 0.857675 0.651740 0.031 Uiso 1 1 calc R U . . .
C26 C -0.1663(3) 0.9119(3) 0.64908(7) 0.0300(4) Uani 1 1 d . . . . .
H26 H -0.189147 0.916182 0.610430 0.036 Uiso 1 1 calc R U . . .
C27 C -0.3074(2) 0.9417(3) 0.68090(8) 0.0304(4) Uani 1 1 d . . . . .
H27 H -0.424235 0.967259 0.663596 0.036 Uiso 1 1 calc R U . . .
C28 C -0.2759(2) 0.9338(3) 0.73652(8) 0.0270(4) Uani 1 1 d . . . . .
H28 H -0.371678 0.953273 0.757521 0.032 Uiso 1 1 calc R U . . .
C29 C -0.1031(2) 0.8971(2) 0.76335(7) 0.0221(3) Uani 1 1 d . . . . .
C30 C 0.0394(2) 0.8695(2) 0.73123(7) 0.0212(3) Uani 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 C7 1.206(2) . ?
O2 C8 1.207(2) . ?
O3 C9 1.205(2) . ?
O4 C10 1.2085(19) . ?
O5 C12 1.208(2) . ?
O6 H6 0.8400 . ?
O6 C12 1.322(2) . ?
O7 C17 1.219(2) . ?
O8 H8 0.8400 . ?
O8 C17 1.312(2) . ?
N1 C7 1.3978(19) . ?
N1 C8 1.4055(19) . ?
N1 C11 1.4686(18) . ?
N2 C9 1.4044(19) . ?
N2 C10 1.4033(19) . ?
N2 C16 1.4694(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.490(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.494(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 C6 1.391(2) . ?
C5 C9 1.498(2) . ?
C6 C10 1.483(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.530(2) . ?
C11 C13 1.534(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.536(2) . ?
C13 C15 1.530(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.520(2) . ?
C16 C18 1.541(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.536(2) . ?
C18 C20 1.527(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.361(3) . ?
C21 C29 1.421(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.408(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(3) . ?
C24 H24 0.9500 . ?
C24 C30 1.418(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.366(3) . ?
C25 C30 1.419(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.414(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.367(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.414(2) . ?
C29 C30 1.426(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
C12 O6 H6 109.5 . . ?
C17 O8 H8 109.5 . . ?
C7 N1 C8 112.33(12) . . ?
C7 N1 C11 123.09(13) . . ?
C8 N1 C11 124.55(13) . . ?
C9 N2 C16 130.63(13) . . ?
C10 N2 C9 111.70(12) . . ?
C10 N2 C16 117.65(12) . . ?
C2 C1 H1 123.0 . . ?
C2 C1 C6 113.93(14) . . ?
C6 C1 H1 123.0 . . ?
C1 C2 C3 123.23(14) . . ?
C1 C2 C7 128.45(14) . . ?
C3 C2 C7 108.32(13) . . ?
C2 C3 C8 108.18(13) . . ?
C4 C3 C2 122.62(14) . . ?
C4 C3 C8 129.20(14) . . ?
C3 C4 H4 122.9 . . ?
C5 C4 C3 114.22(14) . . ?
C5 C4 H4 122.9 . . ?
C4 C5 C6 122.99(14) . . ?
C4 C5 C9 128.58(14) . . ?
C6 C5 C9 108.41(13) . . ?
C1 C6 C5 122.99(14) . . ?
C1 C6 C10 128.95(14) . . ?
C5 C6 C10 108.03(13) . . ?
O1 C7 N1 125.16(14) . . ?
O1 C7 C2 129.14(14) . . ?
N1 C7 C2 105.70(12) . . ?
O2 C8 N1 125.05(14) . . ?
O2 C8 C3 129.56(14) . . ?
N1 C8 C3 105.39(13) . . ?
O3 C9 N2 127.12(14) . . ?
O3 C9 C5 127.68(14) . . ?
N2 C9 C5 105.19(13) . . ?
O4 C10 N2 123.83(14) . . ?
O4 C10 C6 129.94(14) . . ?
N2 C10 C6 106.23(12) . . ?
N1 C11 H11 107.6 . . ?
N1 C11 C12 107.65(13) . . ?
N1 C11 C13 111.45(13) . . ?
C12 C11 H11 107.6 . . ?
C12 C11 C13 114.69(13) . . ?
C13 C11 H11 107.6 . . ?
O5 C12 O6 123.66(15) . . ?
O5 C12 C11 125.52(15) . . ?
O6 C12 C11 110.81(13) . . ?
C11 C13 H13 108.6 . . ?
C11 C13 C14 111.90(14) . . ?
C14 C13 H13 108.6 . . ?
C15 C13 C11 110.52(13) . . ?
C15 C13 H13 108.6 . . ?
C15 C13 C14 108.68(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16 106.1 . . ?
N2 C16 C17 110.31(13) . . ?
N2 C16 C18 114.86(12) . . ?
C17 C16 H16 106.1 . . ?
C17 C16 C18 112.61(12) . . ?
C18 C16 H16 106.1 . . ?
O7 C17 O8 123.42(15) . . ?
O7 C17 C16 121.87(15) . . ?
O8 C17 C16 114.71(13) . . ?
C16 C18 H18 109.4 . . ?
C19 C18 C16 109.65(12) . . ?
C19 C18 H18 109.4 . . ?
C20 C18 C16 109.32(12) . . ?
C20 C18 H18 109.4 . . ?
C20 C18 C19 109.69(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21 119.5 . . ?
C22 C21 C29 121.09(16) . . ?
C29 C21 H21 119.5 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.43(17) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.35(18) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C30 120.69(17) . . ?
C30 C24 H24 119.7 . . ?
C26 C25 H25 119.6 . . ?
C26 C25 C30 120.70(17) . . ?
C30 C25 H25 119.6 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.44(17) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.08(17) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.15(17) . . ?
C29 C28 H28 119.4 . . ?
C21 C29 C30 118.54(15) . . ?
C28 C29 C21 122.76(16) . . ?
C28 C29 C30 118.70(16) . . ?
C24 C30 C25 122.20(16) . . ?
C24 C30 C29 118.88(15) . . ?
C25 C30 C29 118.92(15) . . ?

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
N1 C11 C12 O5 -116.98(17) . . . . ?
N1 C11 C12 O6 64.24(17) . . . . ?
N1 C11 C13 C14 -179.12(14) . . . . ?
N1 C11 C13 C15 -57.85(17) . . . . ?
N2 C16 C17 O7 128.29(15) . . . . ?
N2 C16 C17 O8 -52.48(17) . . . . ?
N2 C16 C18 C19 176.93(14) . . . . ?
N2 C16 C18 C20 -62.78(17) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C8 -179.28(15) . . . . ?
C1 C2 C7 O1 -2.2(3) . . . . ?
C1 C2 C7 N1 177.74(16) . . . . ?
C1 C6 C10 O4 -5.0(3) . . . . ?
C1 C6 C10 N2 175.20(16) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C6 C10 -176.57(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C8 O2 -178.31(18) . . . . ?
C2 C3 C8 N1 1.14(18) . . . . ?
C3 C2 C7 O1 177.94(18) . . . . ?
C3 C2 C7 N1 -2.16(18) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C9 178.59(16) . . . . ?
C4 C3 C8 O2 1.9(3) . . . . ?
C4 C3 C8 N1 -178.65(16) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C10 177.04(15) . . . . ?
C4 C5 C9 O3 7.2(3) . . . . ?
C4 C5 C9 N2 -173.30(16) . . . . ?
C5 C6 C10 O4 176.99(18) . . . . ?
C5 C6 C10 N2 -2.83(17) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C2 C7 179.22(16) . . . . ?
C6 C5 C9 O3 -174.63(17) . . . . ?
C6 C5 C9 N2 4.92(17) . . . . ?
C7 N1 C8 O2 176.85(17) . . . . ?
C7 N1 C8 C3 -2.62(18) . . . . ?
C7 N1 C11 C12 -132.91(15) . . . . ?
C7 N1 C11 C13 100.50(18) . . . . ?
C7 C2 C3 C4 -179.58(15) . . . . ?
C7 C2 C3 C8 0.62(18) . . . . ?
C8 N1 C7 O1 -177.10(16) . . . . ?
C8 N1 C7 C2 2.99(18) . . . . ?
C8 N1 C11 C12 49.5(2) . . . . ?
C8 N1 C11 C13 -77.12(19) . . . . ?
C8 C3 C4 C5 179.43(16) . . . . ?
C9 N2 C10 O4 -173.62(16) . . . . ?
C9 N2 C10 C6 6.22(17) . . . . ?
C9 N2 C16 C17 108.94(18) . . . . ?
C9 N2 C16 C18 -19.6(2) . . . . ?
C9 C5 C6 C1 -179.46(15) . . . . ?
C9 C5 C6 C10 -1.29(17) . . . . ?
C10 N2 C9 O3 172.64(17) . . . . ?
C10 N2 C9 C5 -6.91(17) . . . . ?
C10 N2 C16 C17 -72.80(17) . . . . ?
C10 N2 C16 C18 158.64(14) . . . . ?
C11 N1 C7 O1 5.0(3) . . . . ?
C11 N1 C7 C2 -174.89(14) . . . . ?
C11 N1 C8 O2 -5.3(3) . . . . ?
C11 N1 C8 C3 175.22(14) . . . . ?
C12 C11 C13 C14 58.25(18) . . . . ?
C12 C11 C13 C15 179.52(13) . . . . ?
C13 C11 C12 O5 7.7(2) . . . . ?
C13 C11 C12 O6 -171.09(13) . . . . ?
C16 N2 C9 O3 -9.0(3) . . . . ?
C16 N2 C9 C5 171.43(15) . . . . ?
C16 N2 C10 O4 7.8(2) . . . . ?
C16 N2 C10 C6 -172.36(13) . . . . ?
C17 C16 C18 C19 49.53(18) . . . . ?
C17 C16 C18 C20 169.82(13) . . . . ?
C18 C16 C17 O7 -101.94(17) . . . . ?
C18 C16 C17 O8 77.29(16) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C21 C29 C30 C24 0.0(2) . . . . ?
C21 C29 C30 C25 -179.95(17) . . . . ?
C22 C21 C29 C28 -178.20(18) . . . . ?
C22 C21 C29 C30 0.8(3) . . . . ?
C22 C23 C24 C30 1.0(3) . . . . ?
C23 C24 C30 C25 179.06(18) . . . . ?
C23 C24 C30 C29 -0.9(3) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C26 C25 C30 C24 -179.34(18) . . . . ?
C26 C25 C30 C29 0.6(3) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C27 C28 C29 C21 179.45(18) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C28 C29 C30 C24 179.03(17) . . . . ?
C28 C29 C30 C25 -0.9(2) . . . . ?
C29 C21 C22 C23 -0.7(3) . . . . ?
C30 C25 C26 C27 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.690
####################################################################### 
# 
# 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_omr001_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2373409'
loop_
_audit_author_name
_audit_author_address
'Shogo Morisako'
;Sagami Chemical Research Institute
Japan
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O8'
_chemical_formula_sum            'C20 H20 N2 O8'
_chemical_formula_weight         416.38
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   28.6709(4)
_cell_length_b                   5.29200(10)
_cell_length_c                   13.0480(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.4960(10)
_cell_angle_gamma                90
_cell_volume                     1946.60(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6808
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.7870
_cell_measurement_theta_min      3.1310
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8142
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.620
_diffrn_reflns_theta_min         3.135
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  76.00   0.50    0.50    --  115.73 -63.00  60.00   76
  2  ω     31.00  62.00   0.50    0.50    --  115.73 -63.00  30.00   62
  3  ω     30.00  68.00   0.50    0.50    --  115.73 -63.00 -30.00   76
  4  ω     32.00  57.00   0.50    0.50    --  115.73 -50.00  30.00   50
  5  ω     32.00  58.00   0.50    0.50    --  115.73 -50.00 150.00   52
  6  ω     31.00  56.00   0.50    0.50    --  115.73 -50.00  60.00   50
  7  ω    -85.00 -17.00   0.50    0.50    --    0.00 -44.00 165.00  136
  8  ω    -27.00  35.00   0.50    0.50    --   57.86 -44.00 165.00  124
  9  ω    104.00 167.00   0.50    0.50    --  115.73 111.00  60.00  126
 10  ω     31.00  57.00   0.50    0.50    --  115.73 -50.00-150.00   52
 11  ω     34.00  64.00   0.50    0.50    --  115.73 -63.00-180.00   60
 12  ω     78.00 106.00   0.50    0.50    --  115.73 -91.00-120.00   56
 13  ω     19.00  67.00   0.50    0.50    --  115.73 -91.00-120.00   96
 14  ω    115.00 140.00   0.50    0.50    --  115.73  77.00  30.00   50
 15  ω     73.00 101.00   0.50    0.50    --  115.73  77.00  30.00   56
 16  ω     23.00  89.00   0.50    0.50    --   57.86  61.00  30.00  132
 17  ω     93.00 128.00   0.50    0.50    --   57.86  61.00  30.00   70
 18  ω     17.00 130.00   0.50    0.50    --   57.86  61.00  60.00  226
 19  ω     -2.00  54.00   0.50    0.50    --    0.00  44.00 -44.00  112
 20  ω      6.00  70.00   0.50    0.50    --   57.86  44.00 -44.00  128
 21  ω     76.00 123.00   0.50    0.50    --   57.86  44.00 -44.00   94
 22  ω     94.00 178.00   0.50    0.50    --  115.73  44.00 -44.00  168
 23  ω     59.00  90.00   0.50    0.50    --  115.73  44.00 -44.00   62
 24  ω     42.00  70.00   0.50    0.50    --  115.73  37.00 150.00   56
 25  ω     76.00 103.00   0.50    0.50    --  115.73  37.00 150.00   54
 26  ω    107.00 162.00   0.50    0.50    --  115.73  37.00 150.00  110
 27  ω    108.00 138.00   0.50    0.50    --   57.86   0.00 120.00   60
 28  ω     21.00 106.00   0.50    0.50    --  115.73 -91.00 150.00  170
 29  ω    111.00 138.00   0.50    0.50    --  115.73   0.00 120.00   54
 30  ω    153.00 178.00   0.50    0.50    --  115.73   0.00 120.00   50
 31  ω    114.00 163.00   0.50    0.50    --  115.73   0.00  30.00   98
 32  ω    115.00 140.00   0.50    0.50    --   57.86   0.00 -90.00   50
 33  ω    130.00 156.00   0.50    0.50    --  115.73   0.00-120.00   52
 34  ω   -102.00 -77.00   0.50    0.50    --    0.00   0.00-120.00   50
 35  ω    -72.00 -39.00   0.50    0.50    -- -106.00  63.00  90.00   66
 36  ω    -65.00 -24.00   0.50    0.50    -- -106.00  63.00  30.00   82
 37  ω    -72.00 -26.00   0.50    0.50    -- -106.00  63.00   0.00   92
 38  ω    -48.00  21.00   0.50    0.50    --  -57.86  45.00  90.00  138
 39  ω    -16.00  25.00   0.50    0.50    --  -57.86  45.00 120.00   82
 40  ω    -13.00  19.00   0.50    0.50    --  -57.86  15.00  30.00   64
 41  ω    -24.00  16.00   0.50    0.50    --  -57.86  30.00  90.00   80
 42  ω    -10.00  16.00   0.50    0.50    --  -57.86  15.00  60.00   52
 43  ω   -126.00 -80.00   0.50    0.50    -- -106.00   0.00-150.00   92
 44  ω   -173.00-148.00   0.50    0.50    -- -106.00   0.00-150.00   50
 45  ω    -86.00 -60.00   0.50    0.50    -- -106.00 -77.00  60.00   52
 46  ω    -83.00 -58.00   0.50    0.50    -- -106.00 -77.00  90.00   50
 47  ω   -141.00 -64.00   0.50    0.50    -- -106.00 -63.00  60.00  154
 48  ω   -126.00 -58.00   0.50    0.50    -- -106.00 -77.00  30.00  136
 49  ω    -94.00 -66.00   0.50    0.50    -- -106.00 -63.00  30.00   56
 50  ω   -143.00-117.00   0.50    0.50    --  -57.86 -61.00   0.00   52
 51  ω    -95.00 -58.00   0.50    0.50    -- -106.00 -50.00  90.00   74
 52  ω   -137.00 -60.00   0.50    0.50    -- -106.00 -50.00  60.00  154
 53  ω   -161.00-102.00   0.50    0.50    -- -106.00 -50.00  90.00  118
 54  ω   -113.00 -68.00   0.50    0.50    -- -106.00 -44.00 165.00   90
 55  ω    -67.00 -17.00   0.50    0.50    --  -57.86 -61.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493216000
_diffrn_orient_matrix_UB_12      -0.0793297000
_diffrn_orient_matrix_UB_13      0.0589914000
_diffrn_orient_matrix_UB_21      -0.0233556000
_diffrn_orient_matrix_UB_22      -0.1407846000
_diffrn_orient_matrix_UB_23      0.0808481000
_diffrn_orient_matrix_UB_31      -0.0025639000
_diffrn_orient_matrix_UB_32      -0.2421622000
_diffrn_orient_matrix_UB_33      -0.0663718000
_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3663
_reflns_number_total             3749
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.6052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59706(4) 0.9610(3) 0.25868(10) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.55980(4) 0.2608(2) 0.05422(9) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.38757(4) 0.0955(2) 0.25987(9) 0.0191(3) Uani 1 1 d . . . . .
O4 O 0.43002(4) 0.7978(2) 0.46021(9) 0.0193(3) Uani 1 1 d . . . . .
O5 O 0.56659(5) 0.7459(3) -0.06796(10) 0.0243(3) Uani 1 1 d . . . . .
O6 O 0.63786(5) 0.9245(3) -0.06181(10) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.625976 0.971947 -0.122372 0.037 Uiso 1 1 calc R U . . .
O7 O 0.33435(5) 0.0392(3) 0.49807(11) 0.0252(3) Uani 1 1 d . . . . .
O8 O 0.39845(5) 0.2608(3) 0.57281(10) 0.0226(3) Uani 1 1 d . . . . .
H8 H 0.399365 0.154591 0.620970 0.034 Uiso 1 1 calc R U . . .
N1 N 0.58653(5) 0.6347(3) 0.13984(11) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.39822(5) 0.4394(3) 0.37070(11) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.50745(6) 0.7386(3) 0.32488(13) 0.0154(3) Uani 1 1 d . . . . .
H1 H 0.516197 0.882057 0.367855 0.018 Uiso 1 1 calc R U . . .
C2 C 0.53300(6) 0.6570(3) 0.25066(13) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.52082(6) 0.4446(3) 0.18826(12) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.48154(6) 0.2965(3) 0.19511(13) 0.0149(3) Uani 1 1 d . . . . .
H4 H 0.473141 0.151103 0.153104 0.018 Uiso 1 1 calc R U . . .
C5 C 0.45556(6) 0.3795(3) 0.26881(13) 0.0149(3) Uani 1 1 d . . . . .
C6 C 0.46807(6) 0.5923(3) 0.33074(13) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.57548(6) 0.7753(3) 0.22095(12) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.55627(6) 0.4237(3) 0.11668(12) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.41044(6) 0.2785(3) 0.29576(12) 0.0152(3) Uani 1 1 d . . . . .
C10 C 0.43169(6) 0.6326(3) 0.39710(13) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.62609(6) 0.7055(3) 0.08872(14) 0.0167(4) Uani 1 1 d . . . . .
H11 H 0.641172 0.857845 0.126313 0.020 Uiso 1 1 calc R U . . .
C12 C 0.60603(6) 0.7901(3) -0.02248(13) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.66486(6) 0.4987(4) 0.10006(15) 0.0219(4) Uani 1 1 d . . . . .
H13 H 0.652171 0.349214 0.056976 0.026 Uiso 1 1 calc R U . . .
C14 C 0.70979(7) 0.5934(5) 0.06373(17) 0.0332(5) Uani 1 1 d . . . . .
H14A H 0.702237 0.635588 -0.010578 0.050 Uiso 1 1 calc R U . . .
H14B H 0.734052 0.460802 0.074907 0.050 Uiso 1 1 calc R U . . .
H14C H 0.721749 0.744096 0.103670 0.050 Uiso 1 1 calc R U . . .
C15 C 0.67771(7) 0.4178(5) 0.21422(17) 0.0320(5) Uani 1 1 d . . . . .
H15A H 0.688195 0.565510 0.257613 0.048 Uiso 1 1 calc R U . . .
H15B H 0.703337 0.292763 0.222012 0.048 Uiso 1 1 calc R U . . .
H15C H 0.649839 0.343076 0.236185 0.048 Uiso 1 1 calc R U . . .
C16 C 0.35498(6) 0.4267(4) 0.41670(13) 0.0169(3) Uani 1 1 d . . . . .
H16 H 0.353297 0.589025 0.455095 0.020 Uiso 1 1 calc R U . . .
C17 C 0.36061(6) 0.2157(3) 0.49849(14) 0.0179(4) Uani 1 1 d . . . . .
C18 C 0.30873(6) 0.4068(4) 0.33660(14) 0.0189(4) Uani 1 1 d . . . . .
H18 H 0.304902 0.229394 0.309991 0.023 Uiso 1 1 calc R U . . .
C19 C 0.26738(7) 0.4716(4) 0.39174(16) 0.0259(4) Uani 1 1 d . . . . .
H19A H 0.268307 0.360486 0.452174 0.039 Uiso 1 1 calc R U . . .
H19B H 0.237300 0.447715 0.343309 0.039 Uiso 1 1 calc R U . . .
H19C H 0.270098 0.647929 0.414984 0.039 Uiso 1 1 calc R U . . .
C20 C 0.30913(7) 0.5857(4) 0.24521(15) 0.0236(4) Uani 1 1 d . . . . .
H20A H 0.315285 0.758334 0.271349 0.035 Uiso 1 1 calc R U . . .
H20B H 0.278290 0.579477 0.198299 0.035 Uiso 1 1 calc R U . . .
H20C H 0.334074 0.534228 0.207221 0.035 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 C7 1.217(2) . ?
O2 C8 1.204(2) . ?
O3 C9 1.215(2) . ?
O4 C10 1.208(2) . ?
O5 C12 1.201(2) . ?
O6 H6 0.8400 . ?
O6 C12 1.331(2) . ?
O7 C17 1.199(2) . ?
O8 H8 0.8400 . ?
O8 C17 1.338(2) . ?
N1 C7 1.377(2) . ?
N1 C8 1.413(2) . ?
N1 C11 1.465(2) . ?
N2 C9 1.389(2) . ?
N2 C10 1.401(2) . ?
N2 C16 1.474(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.382(3) . ?
C2 C3 1.394(2) . ?
C2 C7 1.483(2) . ?
C3 C4 1.388(2) . ?
C3 C8 1.504(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.394(2) . ?
C5 C9 1.500(2) . ?
C6 C10 1.487(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.527(2) . ?
C11 C13 1.548(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.535(3) . ?
C13 C15 1.529(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.533(2) . ?
C16 C18 1.535(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.534(2) . ?
C18 C20 1.524(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O6 H6 109.5 . . ?
C17 O8 H8 109.5 . . ?
C7 N1 C8 111.91(14) . . ?
C7 N1 C11 121.15(15) . . ?
C8 N1 C11 126.93(14) . . ?
C9 N2 C10 111.78(14) . . ?
C9 N2 C16 126.68(15) . . ?
C10 N2 C16 121.49(14) . . ?
C2 C1 H1 123.0 . . ?
C6 C1 H1 123.0 . . ?
C6 C1 C2 113.90(16) . . ?
C1 C2 C3 123.47(16) . . ?
C1 C2 C7 127.97(17) . . ?
C3 C2 C7 108.54(14) . . ?
C2 C3 C8 107.22(14) . . ?
C4 C3 C2 122.49(16) . . ?
C4 C3 C8 130.26(16) . . ?
C3 C4 H4 122.9 . . ?
C3 C4 C5 114.15(15) . . ?
C5 C4 H4 122.9 . . ?
C4 C5 C6 122.84(16) . . ?
C4 C5 C9 130.03(16) . . ?
C6 C5 C9 107.09(15) . . ?
C1 C6 C5 123.14(16) . . ?
C1 C6 C10 128.20(16) . . ?
C5 C6 C10 108.63(15) . . ?
O1 C7 N1 125.19(16) . . ?
O1 C7 C2 128.08(16) . . ?
N1 C7 C2 106.73(15) . . ?
O2 C8 N1 125.96(15) . . ?
O2 C8 C3 128.51(16) . . ?
N1 C8 C3 105.50(14) . . ?
O3 C9 N2 124.94(16) . . ?
O3 C9 C5 128.47(16) . . ?
N2 C9 C5 106.58(14) . . ?
O4 C10 N2 125.81(16) . . ?
O4 C10 C6 128.29(17) . . ?
N2 C10 C6 105.90(14) . . ?
N1 C11 H11 106.5 . . ?
N1 C11 C12 108.58(14) . . ?
N1 C11 C13 112.19(14) . . ?
C12 C11 H11 106.5 . . ?
C12 C11 C13 115.96(14) . . ?
C13 C11 H11 106.5 . . ?
O5 C12 O6 124.31(16) . . ?
O5 C12 C11 124.77(16) . . ?
O6 C12 C11 110.90(14) . . ?
C11 C13 H13 108.9 . . ?
C14 C13 C11 111.61(16) . . ?
C14 C13 H13 108.9 . . ?
C15 C13 C11 109.43(16) . . ?
C15 C13 H13 108.9 . . ?
C15 C13 C14 108.99(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16 106.6 . . ?
N2 C16 C17 109.09(14) . . ?
N2 C16 C18 114.34(14) . . ?
C17 C16 H16 106.6 . . ?
C17 C16 C18 113.11(15) . . ?
C18 C16 H16 106.6 . . ?
O7 C17 O8 124.59(17) . . ?
O7 C17 C16 125.30(17) . . ?
O8 C17 C16 110.08(15) . . ?
C16 C18 H18 109.1 . . ?
C19 C18 C16 108.11(15) . . ?
C19 C18 H18 109.1 . . ?
C20 C18 C16 111.18(15) . . ?
C20 C18 H18 109.1 . . ?
C20 C18 C19 110.17(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
N1 C11 C12 O5 -17.1(2) . . . . ?
N1 C11 C12 O6 161.57(14) . . . . ?
N1 C11 C13 C14 -169.83(15) . . . . ?
N1 C11 C13 C15 -49.1(2) . . . . ?
N2 C16 C17 O7 -122.88(19) . . . . ?
N2 C16 C17 O8 59.05(18) . . . . ?
N2 C16 C18 C19 -163.94(15) . . . . ?
N2 C16 C18 C20 -42.9(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C8 178.59(15) . . . . ?
C1 C2 C7 O1 3.0(3) . . . . ?
C1 C2 C7 N1 -176.54(17) . . . . ?
C1 C6 C10 O4 -1.7(3) . . . . ?
C1 C6 C10 N2 177.37(16) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C2 C1 C6 C10 -176.58(16) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C8 O2 176.12(17) . . . . ?
C2 C3 C8 N1 -2.04(18) . . . . ?
C3 C2 C7 O1 -178.70(17) . . . . ?
C3 C2 C7 N1 1.74(18) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C9 177.13(16) . . . . ?
C4 C3 C8 O2 -5.8(3) . . . . ?
C4 C3 C8 N1 176.07(17) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C10 177.60(16) . . . . ?
C4 C5 C9 O3 2.2(3) . . . . ?
C4 C5 C9 N2 -176.68(17) . . . . ?
C5 C6 C10 O4 -179.49(17) . . . . ?
C5 C6 C10 N2 -0.48(18) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C2 C7 177.11(16) . . . . ?
C6 C5 C9 O3 179.98(17) . . . . ?
C6 C5 C9 N2 1.08(18) . . . . ?
C7 N1 C8 O2 -174.95(16) . . . . ?
C7 N1 C8 C3 3.27(18) . . . . ?
C7 N1 C11 C12 -112.29(17) . . . . ?
C7 N1 C11 C13 118.23(18) . . . . ?
C7 C2 C3 C4 -178.07(15) . . . . ?
C7 C2 C3 C8 0.22(18) . . . . ?
C8 N1 C7 O1 177.27(16) . . . . ?
C8 N1 C7 C2 -3.16(18) . . . . ?
C8 N1 C11 C12 68.8(2) . . . . ?
C8 N1 C11 C13 -60.6(2) . . . . ?
C8 C3 C4 C5 -177.51(16) . . . . ?
C9 N2 C10 O4 -179.74(17) . . . . ?
C9 N2 C10 C6 1.21(18) . . . . ?
C9 N2 C16 C17 77.8(2) . . . . ?
C9 N2 C16 C18 -49.9(2) . . . . ?
C9 C5 C6 C1 -178.33(16) . . . . ?
C9 C5 C6 C10 -0.36(18) . . . . ?
C10 N2 C9 O3 179.62(16) . . . . ?
C10 N2 C9 C5 -1.43(18) . . . . ?
C10 N2 C16 C17 -105.02(18) . . . . ?
C10 N2 C16 C18 127.22(17) . . . . ?
C11 N1 C7 O1 -1.8(3) . . . . ?
C11 N1 C7 C2 177.82(14) . . . . ?
C11 N1 C8 O2 4.0(3) . . . . ?
C11 N1 C8 C3 -177.78(15) . . . . ?
C12 C11 C13 C14 64.6(2) . . . . ?
C12 C11 C13 C15 -174.65(16) . . . . ?
C13 C11 C12 O5 110.2(2) . . . . ?
C13 C11 C12 O6 -71.07(19) . . . . ?
C16 N2 C9 O3 -3.0(3) . . . . ?
C16 N2 C9 C5 175.96(15) . . . . ?
C16 N2 C10 O4 2.7(3) . . . . ?
C16 N2 C10 C6 -176.34(14) . . . . ?
C17 C16 C18 C19 70.38(19) . . . . ?
C17 C16 C18 C20 -168.56(15) . . . . ?
C18 C16 C17 O7 5.6(2) . . . . ?
C18 C16 C17 O8 -172.50(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.546
_oxdiff_exptl_absorpt_empirical_full_min 0.556
