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

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

data_ahb-5-84
_database_code_depnum_ccdc_archive 'CCDC 2101459'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;CCART CREAIT Memorial University of Newfounland
Canada
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 N O7'
_chemical_formula_sum            'C23 H27 N O7'
_chemical_formula_weight         429.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H27NO7
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.24253(9)
_cell_length_b                   10.98466(11)
_cell_length_c                   12.92511(13)
_cell_angle_alpha                111.4045(10)
_cell_angle_beta                 93.4027(8)
_cell_angle_gamma                104.9018(9)
_cell_volume                     1037.52(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    36431
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0590
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.224
_diffrn_reflns_theta_min         3.728
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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     -3.00  41.00   0.50    0.05    --   26.00  90.00 171.99   88
  2  ω     36.00 121.00   0.50    0.05    --   47.82  37.00 -30.00  170
  3  ω     35.00 122.00   0.50    0.05    --   47.82  19.00 -90.00  174
  4  ω     25.00 120.00   0.50    0.05    --   47.82  77.00-120.00  190
  5  ω      8.00  39.00   0.50    0.05    --   38.00  92.00 -52.39   62
  6  ω     10.00  43.00   0.50    0.05    --   38.00  89.00  23.75   66
  7  ω    -21.00  43.00   0.50    0.05    --    6.00  86.00  84.54  128
  8  ω     31.00 126.00   0.50    0.05    --   54.00  77.00 178.41  190
  9  ω     43.00 139.00   0.50    0.05    --   66.00  77.00 154.84  192
 10  ω     90.00 149.00   0.50    0.20    --  107.75  77.00  60.00  118
 11  ω     86.00 133.00   0.50    0.20    --  107.75  77.00  90.00   94
 12  ω     85.00 150.00   0.50    0.20    --  107.75  77.00   0.00  130
 13  ω     85.00 154.00   0.50    0.20    --  107.75  77.00  30.00  138
 14  ω     95.00 121.00   0.50    0.20    --  107.75  77.00 -30.00   52
 15  ω    141.00 167.00   0.50    0.20    --  107.75  77.00 -60.00   52
 16  ω     85.00 121.00   0.50    0.20    --  107.75  77.00 -60.00   72
 17  ω     87.00 128.00   0.50    0.20    --  107.75  77.00-120.00   82
 18  ω     70.00 113.00   0.50    0.20    --   90.00  77.00-118.63   86
 19  ω     87.00 125.00   0.50    0.20    --  107.75  77.00-180.00   76
 20  ω    136.00 175.00   0.50    0.20    --  107.75  77.00-180.00   78
 21  ω    144.00 176.00   0.50    0.20    --  107.75  77.00-150.00   64
 22  ω    123.00 176.00   0.50    0.20    --  107.75  77.00 -90.00  106
 23  ω     85.00 117.00   0.50    0.20    --  107.75  77.00 -90.00   64
 24  ω    137.00 168.00   0.50    0.20    --  107.75  77.00 -30.00   62
 25  ω    143.00 177.00   0.50    0.20    --  107.75  77.00 150.00   68
 26  ω     85.00 129.00   0.50    0.20    --  107.75  77.00 150.00   88
 27  ω     93.00 155.00   0.50    0.20    --  107.75  77.00 120.00  124
 28  ω     32.00 126.00   0.50    0.05    --   54.00  76.00 147.57  188
 29  ω     36.00 131.00   0.50    0.05    --   58.00  75.00  -8.85  190
 30  ω     37.00 131.00   0.50    0.05    --   58.00  73.00 -78.67  188
 31  ω     85.00 134.00   0.50    0.20    --  107.75  77.00-150.00   98
 32  ω    134.00 178.00   0.50    0.20    --  107.75  77.00-120.00   88
 33  ω     98.00 124.00   0.50    0.20    --  107.75  61.00 -60.00   52
 34  ω     87.00 171.00   0.50    0.20    --  107.75  73.00 -44.08  168
 35  ω     91.00 160.00   0.50    0.20    --  107.75  61.00-150.00  138
 36  ω    136.00 161.00   0.50    0.20    --  107.75  61.00 -60.00   50
 37  ω     94.00 140.00   0.50    0.20    --  107.75  61.00  60.00   92
 38  ω     91.00 178.00   0.50    0.20    --  107.75  61.00  90.00  174
 39  ω    141.00 175.00   0.50    0.20    --  102.00  71.00 116.87   68
 40  ω     93.00 150.00   0.50    0.20    --  107.75  61.00 150.00  114
 41  ω     82.00 112.00   0.50    0.20    --  102.00  71.00 116.87   60
 42  ω    153.00 178.00   0.50    0.20    --  107.75  61.00  60.00   50
 43  ω     95.00 148.00   0.50    0.20    --  107.75  45.00   0.00  106
 44  ω     98.00 155.00   0.50    0.20    --  107.75  15.00 -60.00  114
 45  ω     95.00 143.00   0.50    0.20    --  107.75  61.00-180.00   96
 46  ω     89.00 178.00   0.50    0.20    --  107.75 135.00-104.00  178
 47  ω     90.00 178.00   0.50    0.20    --  107.75 133.00  76.00  176
 48  ω    140.00 166.00   0.50    0.20    --  107.75 125.00   0.00   52
 49  ω    100.00 137.00   0.50    0.20    --  107.75 125.00   0.00   74
 50  ω     39.00  84.00   0.50    0.20    --  107.75 -77.00-180.00   90
 51  ω     40.00 101.00   0.50    0.05    --   47.82-135.00-170.00  122
 52  ω     39.00 100.00   0.50    0.05    --   47.82-133.00   8.00  122
 53  ω     41.00 120.00   0.50    0.20    --  107.75-136.00  62.76  158
 54  ω     39.00 118.00   0.50    0.20    --  107.75-133.00   8.00  158
 55  ω     36.00  71.00   0.50    0.20    --  107.75-125.00 -30.00   70
 56  ω     77.00 108.00   0.50    0.20    --  107.75-125.00 -30.00   62
 57  ω     40.00 119.00   0.50    0.20    --  107.75-135.00-170.00  158
 58  ω     81.00 112.00   0.50    0.20    --  107.75-125.00 -90.00   62
 59  ω     35.00  76.00   0.50    0.20    --  107.75-125.00 -90.00   82
 60  ω     35.00  97.00   0.50    0.20    --  107.75 -94.00 -30.00  124
 61  ω     36.00 107.00   0.50    0.20    --  107.75-125.00  90.00  142
 62  ω     46.00  96.00   0.50    0.20    --  107.75-125.00 150.00  100
 63  ω     35.00  66.00   0.50    0.20    --  107.75 -94.00  90.00   62
 64  ω     41.00  66.00   0.50    0.20    --  107.75 -94.00 120.00   50
 65  ω     37.00  95.00   0.50    0.20    --  107.75 -94.00 150.00  116
 66  ω     77.00 103.00   0.50    0.20    --  107.75 -94.00 120.00   52
 67  ω     67.00 102.00   0.50    0.20    --  107.75 -94.00  30.00   70
 68  ω     73.00 106.00   0.50    0.20    --  107.75 -94.00  90.00   66
 69  ω     35.00  66.00   0.50    0.20    --  107.75 -94.00   0.00   62
 70  ω     36.00  80.00   0.50    0.20    --  107.75 -94.00 -90.00   88
 71  ω     35.00 105.00   0.50    0.20    --  107.75 -94.00-180.00  140
 72  ω    -93.00 -18.00   0.50    0.05    --  -47.82 135.00-104.00  150
 73  ω    -92.00 -17.00   0.50    0.20    --  -86.25 133.00  76.00  150
 74  ω    -92.00 -17.00   0.50    0.05    --  -47.82 133.00  76.00  150
 75  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  90.00  188
 76  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 120.00  188
 77  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -90.00  188
 78  ω   -135.00 -44.00   0.50    0.05    --  -62.00 -65.00 -81.11  182
 79  ω   -159.00 -63.00   0.50    0.20    --  -86.25 -77.00-180.00  192
 80  ω   -135.00 -38.00   0.50    0.05    --  -62.00 -80.00-146.14  194
 81  ω   -139.00 -43.00   0.50    0.05    --  -66.00 -78.00 -83.88  192
 82  ω   -139.00-112.00   0.50    0.20    --  -86.25 -77.00 -90.00   54
 83  ω    -89.00 -63.00   0.50    0.20    --  -86.25 -77.00 -90.00   52
 84  ω    -90.00 -64.00   0.50    0.20    --  -86.25 -77.00 -30.00   52
 85  ω   -158.00-131.00   0.50    0.20    --  -86.25 -77.00 -30.00   54
 86  ω   -139.00 -42.00   0.50    0.05    --  -66.00 -80.00 100.18  194
 87  ω    -88.00 -63.00   0.50    0.20    --  -86.25 -77.00 120.00   50
 88  ω    -94.00 -63.00   0.50    0.20    --  -86.25 -77.00 112.08   62
 89  ω   -158.00 -63.00   0.50    0.20    --  -86.25 -78.00 141.89  190
 90  ω    -94.00 -63.00   0.50    0.20    --  -86.25 -77.00  60.00   62
 91  ω   -151.00 -55.00   0.50    0.20    --  -78.00 -76.00  54.43  192
 92  ω   -131.00 -35.00   0.50    0.05    --  -58.00 -76.00  44.13  192
 93  ω    -93.00 -63.00   0.50    0.20    --  -86.25 -77.00   0.00   60
 94  ω   -154.00 -60.00   0.50    0.20    --  -82.00 -75.00   9.20  188
 95  ω   -126.00 -31.00   0.50    0.05    --  -54.00 -77.00 -33.41  190
 96  ω   -151.00 -55.00   0.50    0.20    --  -78.00 -76.00-116.62  192
 97  ω   -154.00 -60.00   0.50    0.20    --  -82.00 -75.00-172.21  188
 98  ω    -98.00 -64.00   0.50    0.20    --  -86.25 -75.00-113.68   68
 99  ω    -92.00 -66.00   0.50    0.20    --  -86.25 -74.00-140.52   52
100  ω   -154.00 -61.00   0.50    0.20    --  -82.00 -73.00-142.00  186
101  ω   -154.00 -61.00   0.50    0.20    --  -82.00 -73.00 -77.21  186
102  ω    -98.00 -65.00   0.50    0.20    --  -86.25 -73.00 -22.11   66
103  ω   -139.00 -45.00   0.50    0.05    --  -66.00 -72.00   5.87  188
104  ω   -119.00 -65.00   0.50    0.20    --  -86.25 -72.00  33.47  108
105  ω    -93.00 -65.00   0.50    0.20    --  -86.25 -72.00 148.04   56
106  ω    -91.00 -65.00   0.50    0.20    --  -86.25 -72.00  85.71   52
107  ω    -92.00 -66.00   0.50    0.20    --  -86.25 -71.00  73.41   52
108  ω   -151.00 -58.00   0.50    0.20    --  -78.00 -69.00 -66.76  186
109  ω   -146.00 -56.00   0.50    0.20    --  -74.00 -66.00-178.00  180
110  ω   -119.00 -67.00   0.50    0.05    --  -47.82-135.00-170.00  104
111  ω   -159.00 -67.00   0.50    0.20    --  -86.25-135.00-170.00  184
112  ω   -159.00 -68.00   0.50    0.20    --  -86.25-133.00   8.00  182
113  ω   -119.00 -68.00   0.50    0.05    --  -47.82-133.00   8.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1249135000
_diffrn_orient_matrix_UB_12      0.1257644000
_diffrn_orient_matrix_UB_13      0.0959731000
_diffrn_orient_matrix_UB_21      -0.0855333000
_diffrn_orient_matrix_UB_22      -0.0466970000
_diffrn_orient_matrix_UB_23      0.0875584000
_diffrn_orient_matrix_UB_31      0.1249187000
_diffrn_orient_matrix_UB_32      -0.0832970000
_diffrn_orient_matrix_UB_33      -0.0012570000
_diffrn_oxdiff_digest_frames     
;
012572d4ae9beed76ff333c02c615ee36b13182ea1a
;
_diffrn_oxdiff_digest_hkl        
;
01277a49e9a46b99574af27218b0f9eaba3cc8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4185
_reflns_number_total             4341
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.037
_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)+(0.0398P)²+0.4393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C)
;
_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 0.72984(9) 0.21478(8) 0.20029(6) 0.01761(16) Uani 1 1 d . . . . .
O2 O 0.49801(9) 0.43563(7) 0.82649(6) 0.01932(17) Uani 1 1 d . . . . .
O3 O 0.37468(9) 0.23037(7) 0.83059(6) 0.01608(16) Uani 1 1 d . . . . .
O4 O 0.16723(9) 0.02694(7) 0.58786(6) 0.01768(16) Uani 1 1 d . . . . .
O5 O 0.01352(9) 0.13288(7) 0.70885(6) 0.01734(16) Uani 1 1 d . . . . .
O6 O -0.08501(10) 0.54995(8) 0.75106(7) 0.02308(18) Uani 1 1 d . . . . .
O7 O 0.02120(10) 0.60304(8) 0.93137(6) 0.02054(17) Uani 1 1 d . . . . .
N1 N 0.30353(11) 0.33066(8) 0.50825(7) 0.01390(17) Uani 1 1 d . . . . .
C1 C 0.40686(13) 0.31585(10) 0.42771(8) 0.0141(2) Uani 1 1 d . . . . .
C2 C 0.40621(13) 0.35340(10) 0.33505(8) 0.0155(2) Uani 1 1 d . . . . .
H2 H 0.331250 0.401143 0.322190 0.019 Uiso 1 1 calc R . . . .
C3 C 0.51907(13) 0.31803(10) 0.26345(8) 0.0159(2) Uani 1 1 d . . . . .
H3 H 0.522063 0.341906 0.199807 0.019 Uiso 1 1 calc R . . . .
C4 C 0.63047(13) 0.24697(10) 0.28268(8) 0.0147(2) Uani 1 1 d . . . . .
C5 C 0.63645(13) 0.21422(10) 0.37635(8) 0.0146(2) Uani 1 1 d . . . . .
H5 H 0.714078 0.168789 0.389722 0.017 Uiso 1 1 calc R . . . .
C6 C 0.52264(13) 0.25096(10) 0.45136(8) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.48992(13) 0.23051(10) 0.55249(8) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.35541(13) 0.27975(10) 0.58377(8) 0.01336(19) Uani 1 1 d . . . . .
C9 C 0.25919(12) 0.27801(10) 0.68019(8) 0.0133(2) Uani 1 1 d . . . . .
C10 C 0.14312(12) 0.37028(10) 0.69586(8) 0.0138(2) Uani 1 1 d . . . . .
C11 C 0.04446(13) 0.34653(10) 0.58470(8) 0.0158(2) Uani 1 1 d . . . . .
H11A H -0.041118 0.396987 0.597602 0.019 Uiso 1 1 calc R . . . .
H11B H -0.015861 0.247679 0.543003 0.019 Uiso 1 1 calc R . . . .
C12 C 0.17038(13) 0.39739(10) 0.51672(8) 0.0152(2) Uani 1 1 d . . . . .
H12A H 0.110734 0.375449 0.440436 0.018 Uiso 1 1 calc R . . . .
H12B H 0.221188 0.498064 0.554481 0.018 Uiso 1 1 calc R . . . .
C13 C 0.85186(14) 0.15045(11) 0.21785(9) 0.0197(2) Uani 1 1 d . . . . .
H13A H 0.906923 0.124670 0.151313 0.030 Uiso 1 1 calc GR . . . .
H13B H 0.794852 0.068181 0.230328 0.030 Uiso 1 1 calc GR . . . .
H13C H 0.937986 0.214104 0.284013 0.030 Uiso 1 1 calc GR . . . .
C14 C 0.58850(13) 0.16948(11) 0.61095(9) 0.0171(2) Uani 1 1 d . . . . .
H14A H 0.642886 0.111276 0.556580 0.026 Uiso 1 1 calc GR . . . .
H14B H 0.510860 0.114203 0.642737 0.026 Uiso 1 1 calc GR . . . .
H14C H 0.676057 0.243145 0.671669 0.026 Uiso 1 1 calc GR . . . .
C15 C 0.39149(13) 0.32556(10) 0.78739(8) 0.01371(19) Uani 1 1 d . . . . .
C16 C 0.50554(14) 0.26489(11) 0.92711(9) 0.0184(2) Uani 1 1 d . . . . .
H16A H 0.496876 0.344694 0.992026 0.022 Uiso 1 1 calc R . . . .
H16B H 0.620501 0.288190 0.907362 0.022 Uiso 1 1 calc R . . . .
C17 C 0.47594(15) 0.14126(12) 0.95653(9) 0.0231(2) Uani 1 1 d . . . . .
H17A H 0.478907 0.061885 0.890434 0.035 Uiso 1 1 calc GR . . . .
H17B H 0.364433 0.122333 0.979955 0.035 Uiso 1 1 calc GR . . . .
H17C H 0.565224 0.159077 1.018358 0.035 Uiso 1 1 calc GR . . . .
C18 C 0.14271(12) 0.12905(10) 0.65192(8) 0.01355(19) Uani 1 1 d . . . . .
C19 C -0.11597(13) 0.00306(10) 0.68704(9) 0.0167(2) Uani 1 1 d . . . . .
H19A H -0.062960 -0.071580 0.672573 0.020 Uiso 1 1 calc R . . . .
H19B H -0.202142 -0.021140 0.620406 0.020 Uiso 1 1 calc R . . . .
C20 C -0.19733(16) 0.02312(12) 0.79035(10) 0.0267(3) Uani 1 1 d . . . . .
H20A H -0.293024 -0.058489 0.776541 0.040 Uiso 1 1 calc GR . . . .
H20B H -0.238909 0.103164 0.808067 0.040 Uiso 1 1 calc GR . . . .
H20C H -0.113232 0.037781 0.853942 0.040 Uiso 1 1 calc GR . . . .
C21 C 0.13349(13) 0.45844(10) 0.79700(9) 0.0153(2) Uani 1 1 d . . . . .
H21 H 0.210450 0.469699 0.859837 0.018 Uiso 1 1 calc R . . . .
C22 C 0.01227(13) 0.54007(10) 0.81897(9) 0.0166(2) Uani 1 1 d . . . . .
C23 C -0.10570(15) 0.67223(12) 0.96443(10) 0.0243(2) Uani 1 1 d . . . . .
H23A H -0.219571 0.606223 0.933478 0.037 Uiso 1 1 calc GR . . . .
H23B H -0.092048 0.744507 0.935394 0.037 Uiso 1 1 calc GR . . . .
H23C H -0.091731 0.712997 1.046900 0.037 Uiso 1 1 calc GR . . . .


_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 C4 1.3811(12) . ?
O1 C13 1.4206(13) . ?
O2 C15 1.2014(13) . ?
O3 C15 1.3361(12) . ?
O3 C16 1.4656(12) . ?
O4 C18 1.2013(13) . ?
O5 C18 1.3306(12) . ?
O5 C19 1.4630(12) . ?
O6 C22 1.2065(13) . ?
O7 C22 1.3499(13) . ?
O7 C23 1.4420(13) . ?
N1 C1 1.3742(13) . ?
N1 C8 1.3857(12) . ?
N1 C12 1.4571(13) . ?
C1 C2 1.4020(14) . ?
C1 C6 1.4095(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3778(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.4133(14) . ?
C4 C5 1.3847(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.4141(14) . ?
C6 C7 1.4342(14) . ?
C7 C8 1.3738(14) . ?
C7 C14 1.5025(13) . ?
C8 C9 1.5196(13) . ?
C9 C10 1.5348(13) . ?
C9 C15 1.5432(13) . ?
C9 C18 1.5642(13) . ?
C10 C11 1.5074(13) . ?
C10 C21 1.3345(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5263(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5053(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.4995(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.4804(14) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C4 O1 C13 116.63(8) . . ?
C15 O3 C16 114.99(8) . . ?
C18 O5 C19 117.75(8) . . ?
C22 O7 C23 114.87(9) . . ?
C1 N1 C8 108.30(8) . . ?
C1 N1 C12 125.50(8) . . ?
C8 N1 C12 126.07(9) . . ?
N1 C1 C2 129.69(9) . . ?
N1 C1 C6 107.97(9) . . ?
C2 C1 C6 122.34(9) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.08(9) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.39(9) . . ?
C4 C3 H3 119.3 . . ?
O1 C4 C3 113.74(9) . . ?
O1 C4 C5 124.41(9) . . ?
C5 C4 C3 121.85(9) . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.50(9) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 119.72(9) . . ?
C1 C6 C7 107.39(9) . . ?
C5 C6 C7 132.82(9) . . ?
C6 C7 C14 125.47(9) . . ?
C8 C7 C6 106.11(9) . . ?
C8 C7 C14 128.41(9) . . ?
N1 C8 C9 119.96(9) . . ?
C7 C8 N1 110.20(9) . . ?
C7 C8 C9 129.76(9) . . ?
C8 C9 C10 110.44(8) . . ?
C8 C9 C15 107.90(8) . . ?
C8 C9 C18 109.53(8) . . ?
C10 C9 C15 111.67(8) . . ?
C10 C9 C18 107.44(8) . . ?
C15 C9 C18 109.87(8) . . ?
C11 C10 C9 111.53(8) . . ?
C21 C10 C9 122.53(9) . . ?
C21 C10 C11 125.93(9) . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
C10 C11 C12 108.09(8) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
N1 C12 C11 108.76(8) . . ?
N1 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O3 124.23(9) . . ?
O2 C15 C9 123.36(9) . . ?
O3 C15 C9 112.40(8) . . ?
O3 C16 H16A 110.3 . . ?
O3 C16 H16B 110.3 . . ?
O3 C16 C17 107.30(8) . . ?
H16A C16 H16B 108.5 . . ?
C17 C16 H16A 110.3 . . ?
C17 C16 H16B 110.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 125.50(9) . . ?
O4 C18 C9 124.53(9) . . ?
O5 C18 C9 109.97(8) . . ?
O5 C19 H19A 110.4 . . ?
O5 C19 H19B 110.4 . . ?
O5 C19 C20 106.71(8) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C21 H21 117.4 . . ?
C10 C21 C22 125.13(9) . . ?
C22 C21 H21 117.4 . . ?
O6 C22 O7 122.77(10) . . ?
O6 C22 C21 127.99(10) . . ?
O7 C22 C21 109.21(9) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C4 C5 C6 -178.18(9) . . . . ?
N1 C1 C2 C3 -176.03(10) . . . . ?
N1 C1 C6 C5 175.48(9) . . . . ?
N1 C1 C6 C7 -1.92(11) . . . . ?
N1 C8 C9 C10 -15.03(12) . . . . ?
N1 C8 C9 C15 -137.33(9) . . . . ?
N1 C8 C9 C18 103.10(10) . . . . ?
C1 N1 C8 C7 -0.73(11) . . . . ?
C1 N1 C8 C9 -177.75(8) . . . . ?
C1 N1 C12 C11 158.64(9) . . . . ?
C1 C2 C3 C4 0.02(14) . . . . ?
C1 C6 C7 C8 1.46(11) . . . . ?
C1 C6 C7 C14 -177.48(9) . . . . ?
C2 C1 C6 C5 -3.87(15) . . . . ?
C2 C1 C6 C7 178.73(9) . . . . ?
C2 C3 C4 O1 177.47(9) . . . . ?
C2 C3 C4 C5 -2.56(15) . . . . ?
C3 C4 C5 C6 1.85(14) . . . . ?
C4 C5 C6 C1 1.25(14) . . . . ?
C4 C5 C6 C7 177.87(10) . . . . ?
C5 C6 C7 C8 -175.46(10) . . . . ?
C5 C6 C7 C14 5.60(17) . . . . ?
C6 C1 C2 C3 3.16(14) . . . . ?
C6 C7 C8 N1 -0.47(11) . . . . ?
C6 C7 C8 C9 176.18(9) . . . . ?
C7 C8 C9 C10 168.60(10) . . . . ?
C7 C8 C9 C15 46.30(13) . . . . ?
C7 C8 C9 C18 -73.27(13) . . . . ?
C8 N1 C1 C2 -179.08(10) . . . . ?
C8 N1 C1 C6 1.65(11) . . . . ?
C8 N1 C12 C11 -26.01(13) . . . . ?
C8 C9 C10 C11 45.87(10) . . . . ?
C8 C9 C10 C21 -134.65(10) . . . . ?
C8 C9 C15 O2 59.58(12) . . . . ?
C8 C9 C15 O3 -119.88(9) . . . . ?
C8 C9 C18 O4 24.11(13) . . . . ?
C8 C9 C18 O5 -155.71(8) . . . . ?
C9 C10 C11 C12 -67.77(10) . . . . ?
C9 C10 C21 C22 -173.65(9) . . . . ?
C10 C9 C15 O2 -61.97(13) . . . . ?
C10 C9 C15 O3 118.57(9) . . . . ?
C10 C9 C18 O4 144.09(10) . . . . ?
C10 C9 C18 O5 -35.72(10) . . . . ?
C10 C11 C12 N1 54.46(10) . . . . ?
C10 C21 C22 O6 -6.84(18) . . . . ?
C10 C21 C22 O7 171.37(10) . . . . ?
C11 C10 C21 C22 5.76(16) . . . . ?
C12 N1 C1 C2 -3.04(16) . . . . ?
C12 N1 C1 C6 177.69(9) . . . . ?
C12 N1 C8 C7 -176.74(9) . . . . ?
C12 N1 C8 C9 6.23(14) . . . . ?
C13 O1 C4 C3 176.40(8) . . . . ?
C13 O1 C4 C5 -3.57(14) . . . . ?
C14 C7 C8 N1 178.43(9) . . . . ?
C14 C7 C8 C9 -4.92(17) . . . . ?
C15 O3 C16 C17 -174.54(9) . . . . ?
C15 C9 C10 C11 165.93(8) . . . . ?
C15 C9 C10 C21 -14.59(13) . . . . ?
C15 C9 C18 O4 -94.24(11) . . . . ?
C15 C9 C18 O5 85.94(9) . . . . ?
C16 O3 C15 O2 -4.31(14) . . . . ?
C16 O3 C15 C9 175.15(8) . . . . ?
C18 O5 C19 C20 155.61(9) . . . . ?
C18 C9 C10 C11 -73.54(10) . . . . ?
C18 C9 C10 C21 105.95(10) . . . . ?
C18 C9 C15 O2 178.93(9) . . . . ?
C18 C9 C15 O3 -0.53(11) . . . . ?
C19 O5 C18 O4 -4.01(14) . . . . ?
C19 O5 C18 C9 175.80(8) . . . . ?
C21 C10 C11 C12 112.76(11) . . . . ?
C23 O7 C22 O6 5.78(14) . . . . ?
C23 O7 C22 C21 -172.54(8) . . . . ?

_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_nt186_173k
_database_code_depnum_ccdc_archive 'CCDC 2101461'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;CCART CREAIT Memorial University of Newfounland
Canada
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2020-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O7'
_chemical_formula_sum            'C22 H25 N O7'
_chemical_formula_weight         415.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H25NO7
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1806(3)
_cell_length_b                   11.5207(3)
_cell_length_c                   12.2742(2)
_cell_angle_alpha                70.006(2)
_cell_angle_beta                 77.003(2)
_cell_angle_gamma                88.377(3)
_cell_volume                     1057.73(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.5000
_cell_measurement_theta_min      4.0820
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.442
_diffrn_reflns_theta_min         3.937
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 178.00   0.50    0.50    --  107.75  45.00  30.00  166
  2  ω     95.00 178.00   0.50    0.50    --  107.75  45.00 -30.00  166
  3  ω     95.00 178.00   0.50    0.50    --  107.75  30.00   0.00  166
  4  ω     95.00 178.00   0.50    0.50    --  107.75  45.00 -60.00  166
  5  ω     33.00 122.00   0.50    0.05    --   47.95  13.00  92.00  178
  6  ω     93.00 178.00   0.50    0.50    --  107.75  13.00  92.00  170
  7  ω     95.00 178.00   0.50    0.50    --  107.75  45.00-120.00  166
  8  ω     95.00 178.00   0.50    0.50    --  107.75  45.00-180.00  166
  9  ω     94.00 178.00   0.50    0.50    --  107.75  15.00-180.00  168
 10  ω    -59.00  25.00   0.50    0.05    --  -47.95  57.00 -30.00  168
 11  ω    -16.00  28.00   0.50    0.05    --  -47.95  19.00-150.00   88
 12  ω    -16.00  28.00   0.50    0.05    --  -47.95  19.00-120.00   88
 13  ω    -43.00 -14.00   0.50    0.50    --  -86.25  45.00  60.00   58
 14  ω    -11.00  27.00   0.50    0.05    --  -47.95  13.00  92.00   76
 15  ω     35.00 112.00   0.50    0.50    --  107.75-125.00 120.00  154
 16  ω     35.00 112.00   0.50    0.50    --  107.75-125.00 150.00  154
 17  ω     35.00 107.00   0.50    0.50    --  107.75-102.00  14.36  144
 18  ω     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
 19  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 20  ω     35.00 112.00   0.50    0.50    --  107.75-125.00-120.00  154
 21  ω     35.00 112.00   0.50    0.50    --  107.75-125.00-180.00  154
 22  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00-129.37  142
 23  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00-120.00  142
 24  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00 -90.00  142
 25  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00 -60.00  142
 26  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00  30.00  142
 27  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00  90.00  142
 28  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00 120.00  142
 29  ω     35.00 131.00   0.50    0.50    --  107.75 -77.00 120.00  192
 30  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00 150.00   88
 31  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00 120.00   88
 32  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00  30.00   88
 33  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00   0.00   88
 34  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00 -60.00   88
 35  ω     35.00  79.00   0.50    0.50    --  107.75 -61.00-120.00   88
 36  ω    -26.00  25.00   0.50    0.05    --   47.95 -13.00 -79.00  102
 37  ω    -26.00  30.00   0.50    0.05    --   47.95 -19.00 150.00  112
 38  ω     95.00 178.00   0.50    0.50    --  107.75 125.00  60.00  166
 39  ω   -122.00 -33.00   0.50    0.05    --  -47.95 -13.00 -79.00  178
 40  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -30.00  190
 41  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 150.00  190
 42  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00  60.00  190
 43  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -90.00  190
 44  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00-120.00  190
 45  ω   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00-180.00  190
 46  ω   -120.00 -51.00   0.50    0.05    --  -47.95 -77.00  90.00  138
 47  ω    -86.00 -13.00   0.50    0.05    --  -47.95 125.00-180.00  146
 48  ω    -86.00 -13.00   0.50    0.50    --  -86.25 125.00  90.00  146
 49  ω   -161.00 -71.00   0.50    0.50    --  -86.25 -13.00 -79.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1022263000
_diffrn_orient_matrix_UB_12      0.1168168000
_diffrn_orient_matrix_UB_13      -0.0240958000
_diffrn_orient_matrix_UB_21      -0.1503993000
_diffrn_orient_matrix_UB_22      -0.0756821000
_diffrn_orient_matrix_UB_23      -0.0026572000
_diffrn_orient_matrix_UB_31      -0.0662513000
_diffrn_orient_matrix_UB_32      -0.0305242000
_diffrn_orient_matrix_UB_33      0.1350541000
_diffrn_oxdiff_digest_frames     
;
0121c51874c7844028688461a791bd7cd70003248d0
;
_diffrn_oxdiff_digest_hkl        
;
01631328b65304280523791576368939b8e94d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4027
_reflns_number_total             4446
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.080
_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)+(0.0574P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1122
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C19 \\sim C18-C19A
 with sigma of 0.02
3. Others
 Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C18(H18A,H18B), C18(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C20(H20)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C19(H19A,H19B,
 H19C), C19A(H19D,H19E,H19F), C22(H22A,H22B,H22C)
;
_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 0.07596(13) 0.13857(9) 1.00429(8) 0.0467(2) Uani 1 1 d . . . . .
O2 O 0.48833(12) 0.18842(9) 0.31923(8) 0.0425(2) Uani 1 1 d . . . . .
O3 O 0.71382(11) 0.13189(8) 0.39688(8) 0.0381(2) Uani 1 1 d . . . . .
O4 O 0.87381(11) 0.37405(8) 0.43714(8) 0.0381(2) Uani 1 1 d . . . . .
O5 O 0.86935(11) 0.37552(9) 0.25357(8) 0.0396(2) Uani 1 1 d . . . . .
O6 O 0.30939(11) 0.61771(9) 0.20549(7) 0.0396(2) Uani 1 1 d . . . . .
O7 O 0.51148(12) 0.64316(10) 0.04056(8) 0.0467(2) Uani 1 1 d . . . . .
N1 N 0.37360(12) 0.35020(9) 0.52982(8) 0.0289(2) Uani 1 1 d . . . . .
C1 C 0.28198(14) 0.30909(10) 0.64552(9) 0.0281(2) Uani 1 1 d . . . . .
C2 C 0.11822(15) 0.33116(11) 0.69511(10) 0.0320(2) Uani 1 1 d . . . . .
H2 H 0.051088 0.385102 0.647779 0.038 Uiso 1 1 calc R . . . .
C3 C 0.05810(15) 0.27139(11) 0.81560(11) 0.0359(3) Uani 1 1 d . . . . .
H3 H -0.052618 0.284897 0.852113 0.043 Uiso 1 1 calc R . . . .
C4 C 0.15676(16) 0.19087(11) 0.88581(10) 0.0350(3) Uani 1 1 d . . . . .
C5 C 0.31763(15) 0.16725(11) 0.83742(10) 0.0329(2) Uani 1 1 d . . . . .
H5 H 0.382975 0.112334 0.885570 0.040 Uiso 1 1 calc R . . . .
C6 C 0.38263(14) 0.22721(10) 0.71388(10) 0.0289(2) Uani 1 1 d . . . . .
C7 C 0.53805(14) 0.21877(10) 0.63534(10) 0.0293(2) Uani 1 1 d . . . . .
C8 C 0.52485(14) 0.29496(10) 0.52412(10) 0.0283(2) Uani 1 1 d . . . . .
C9 C 0.61322(14) 0.32554(10) 0.39500(10) 0.0292(2) Uani 1 1 d . . . . .
C10 C 0.50688(14) 0.42721(10) 0.33076(10) 0.0301(2) Uani 1 1 d . . . . .
C11 C 0.34535(14) 0.43325(11) 0.41733(9) 0.0310(2) Uani 1 1 d . . . . .
H11A H 0.328748 0.518304 0.418497 0.037 Uiso 1 1 calc R . . . .
H11B H 0.246882 0.404082 0.397528 0.037 Uiso 1 1 calc R . . . .
C12 C 0.1616(2) 0.04782(15) 1.07841(12) 0.0538(4) Uani 1 1 d . . . . .
H12A H 0.189261 -0.018835 1.045821 0.081 Uiso 1 1 calc GR . . . .
H12B H 0.089604 0.013959 1.158750 0.081 Uiso 1 1 calc GR . . . .
H12C H 0.265299 0.085567 1.081932 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.67983(16) 0.14126(12) 0.67120(11) 0.0379(3) Uani 1 1 d . . . . .
H13A H 0.770436 0.151378 0.600626 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.639878 0.054146 0.708209 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.722046 0.167476 0.728264 0.057 Uiso 1 1 calc GR . . . .
C14 C 0.59655(14) 0.20857(11) 0.36303(10) 0.0310(2) Uani 1 1 d . . . . .
C15 C 0.71691(18) 0.01681(12) 0.37180(14) 0.0444(3) Uani 1 1 d . . . . .
H15A H 0.742754 0.034254 0.284772 0.053 Uiso 1 1 calc R . . . .
H15B H 0.606500 -0.029307 0.407525 0.053 Uiso 1 1 calc R . . . .
C16 C 0.8499(2) -0.05657(14) 0.42496(18) 0.0571(4) Uani 1 1 d . . . . .
H16A H 0.957026 -0.007793 0.392454 0.086 Uiso 1 1 calc GR . . . .
H16B H 0.860972 -0.132745 0.405835 0.086 Uiso 1 1 calc GR . . . .
H16C H 0.819250 -0.077496 0.511620 0.086 Uiso 1 1 calc GR . . . .
C17 C 0.80067(14) 0.36231(10) 0.36692(10) 0.0314(2) Uani 1 1 d . . . . .
C18 C 1.05095(16) 0.40027(16) 0.21416(14) 0.0493(3) Uani 1 1 d D . . . .
H18A H 1.082175 0.474658 0.229557 0.059 Uiso 0.490(5) 1 calc R . P A 1
H18B H 1.107796 0.329490 0.259988 0.059 Uiso 0.490(5) 1 calc R . P A 1
H18C H 1.078978 0.458852 0.131127 0.059 Uiso 0.510(5) 1 calc R . P A 2
H18D H 1.089726 0.439357 0.264914 0.059 Uiso 0.510(5) 1 calc R . P A 2
C19 C 1.1053(4) 0.4194(5) 0.0907(3) 0.0674(12) Uani 0.490(5) 1 d D . P A 1
H19A H 1.066394 0.348533 0.074549 0.101 Uiso 0.490(5) 1 calc GR . P A 1
H19B H 1.228255 0.427953 0.067511 0.101 Uiso 0.490(5) 1 calc GR . P A 1
H19C H 1.058688 0.494807 0.044876 0.101 Uiso 0.490(5) 1 calc GR . P A 1
C19A C 1.1319(4) 0.2944(4) 0.2201(4) 0.0698(12) Uani 0.510(5) 1 d D . P A 2
H19D H 1.109875 0.238382 0.303045 0.105 Uiso 0.510(5) 1 calc GR . P A 2
H19E H 1.253012 0.314093 0.189780 0.105 Uiso 0.510(5) 1 calc GR . P A 2
H19F H 1.091260 0.254383 0.171720 0.105 Uiso 0.510(5) 1 calc GR . P A 2
C20 C 0.55171(15) 0.49712(12) 0.21591(10) 0.0350(3) Uani 1 1 d . . . . .
H20 H 0.657288 0.486132 0.170060 0.042 Uiso 1 1 calc R . . . .
C21 C 0.44307(15) 0.59074(11) 0.15780(10) 0.0337(3) Uani 1 1 d . . . . .
C22 C 0.4129(2) 0.73533(16) -0.02482(12) 0.0560(4) Uani 1 1 d . . . . .
H22A H 0.475190 0.772384 -0.107782 0.084 Uiso 1 1 calc GR . . . .
H22B H 0.390193 0.799759 0.011187 0.084 Uiso 1 1 calc GR . . . .
H22C H 0.306459 0.696454 -0.022262 0.084 Uiso 1 1 calc GR . . . .


_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 C4 1.3805(14) . ?
O1 C12 1.4166(17) . ?
O2 C14 1.1991(14) . ?
O3 C14 1.3243(14) . ?
O3 C15 1.4583(14) . ?
O4 C17 1.1981(14) . ?
O5 C17 1.3352(14) . ?
O5 C18 1.4590(15) . ?
O6 C21 1.2051(16) . ?
O7 C21 1.3458(14) . ?
O7 C22 1.4426(17) . ?
N1 C1 1.3727(14) . ?
N1 C8 1.3740(14) . ?
N1 C11 1.4502(14) . ?
C1 C2 1.3962(16) . ?
C1 C6 1.4133(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3780(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4066(17) . ?
C4 C5 1.3775(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.4146(16) . ?
C6 C7 1.4356(16) . ?
C7 C8 1.3738(16) . ?
C7 C13 1.4962(15) . ?
C8 C9 1.5085(15) . ?
C9 C10 1.5394(15) . ?
C9 C14 1.5442(15) . ?
C9 C17 1.5326(15) . ?
C10 C11 1.5145(16) . ?
C10 C20 1.3335(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.488(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C18 C19 1.420(4) . ?
C18 C19A 1.359(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.4720(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C4 O1 C12 116.87(11) . . ?
C14 O3 C15 116.83(10) . . ?
C17 O5 C18 116.69(10) . . ?
C21 O7 C22 114.97(11) . . ?
C1 N1 C8 109.17(9) . . ?
C1 N1 C11 135.14(9) . . ?
C8 N1 C11 115.68(9) . . ?
N1 C1 C2 130.90(10) . . ?
N1 C1 C6 106.71(10) . . ?
C2 C1 C6 122.29(10) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.18(10) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.57(11) . . ?
C4 C3 H3 119.2 . . ?
O1 C4 C3 113.66(11) . . ?
C5 C4 O1 124.65(11) . . ?
C5 C4 C3 121.68(11) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.01(10) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 119.27(10) . . ?
C1 C6 C7 108.33(10) . . ?
C5 C6 C7 132.34(10) . . ?
C6 C7 C13 125.78(10) . . ?
C8 C7 C6 105.12(9) . . ?
C8 C7 C13 129.10(11) . . ?
N1 C8 C9 108.70(9) . . ?
C7 C8 N1 110.66(10) . . ?
C7 C8 C9 140.03(10) . . ?
C8 C9 C10 102.46(9) . . ?
C8 C9 C14 107.16(9) . . ?
C8 C9 C17 114.38(9) . . ?
C10 C9 C14 110.04(9) . . ?
C17 C9 C10 114.60(9) . . ?
C17 C9 C14 107.90(9) . . ?
C11 C10 C9 109.57(9) . . ?
C20 C10 C9 124.32(11) . . ?
C20 C10 C11 126.11(11) . . ?
N1 C11 C10 102.14(9) . . ?
N1 C11 H11A 111.3 . . ?
N1 C11 H11B 111.3 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 O3 125.45(11) . . ?
O2 C14 C9 124.65(11) . . ?
O3 C14 C9 109.82(9) . . ?
O3 C15 H15A 110.4 . . ?
O3 C15 H15B 110.4 . . ?
O3 C15 C16 106.81(11) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O5 125.78(11) . . ?
O4 C17 C9 124.90(10) . . ?
O5 C17 C9 109.29(9) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.4 . . ?
O5 C18 H18D 109.4 . . ?
H18A C18 H18B 108.1 . . ?
H18C C18 H18D 108.0 . . ?
C19 C18 O5 110.63(17) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19A C18 O5 111.17(19) . . ?
C19A C18 H18C 109.4 . . ?
C19A C18 H18D 109.4 . . ?
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 C19A H19D 109.5 . . ?
C18 C19A H19E 109.5 . . ?
C18 C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C10 C20 H20 118.9 . . ?
C10 C20 C21 122.19(11) . . ?
C21 C20 H20 118.9 . . ?
O6 C21 O7 123.07(11) . . ?
O6 C21 C20 126.17(11) . . ?
O7 C21 C20 110.76(10) . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 C4 C5 C6 179.37(11) . . . . ?
N1 C1 C2 C3 177.20(11) . . . . ?
N1 C1 C6 C5 -178.18(9) . . . . ?
N1 C1 C6 C7 -0.71(12) . . . . ?
N1 C8 C9 C10 11.29(11) . . . . ?
N1 C8 C9 C14 -104.52(10) . . . . ?
N1 C8 C9 C17 135.92(10) . . . . ?
C1 N1 C8 C7 -1.29(13) . . . . ?
C1 N1 C8 C9 171.60(9) . . . . ?
C1 N1 C11 C10 -178.94(11) . . . . ?
C1 C2 C3 C4 -0.40(18) . . . . ?
C1 C6 C7 C8 -0.05(12) . . . . ?
C1 C6 C7 C13 -179.56(11) . . . . ?
C2 C1 C6 C5 -1.46(17) . . . . ?
C2 C1 C6 C7 176.01(10) . . . . ?
C2 C3 C4 O1 -179.56(11) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 0.36(18) . . . . ?
C4 C5 C6 C1 0.56(17) . . . . ?
C4 C5 C6 C7 -176.19(12) . . . . ?
C5 C6 C7 C8 176.97(12) . . . . ?
C5 C6 C7 C13 -2.5(2) . . . . ?
C6 C1 C2 C3 1.36(17) . . . . ?
C6 C7 C8 N1 0.80(12) . . . . ?
C6 C7 C8 C9 -168.68(13) . . . . ?
C7 C8 C9 C10 -179.10(14) . . . . ?
C7 C8 C9 C14 65.08(17) . . . . ?
C7 C8 C9 C17 -54.47(18) . . . . ?
C8 N1 C1 C2 -175.12(11) . . . . ?
C8 N1 C1 C6 1.20(12) . . . . ?
C8 N1 C11 C10 -0.55(12) . . . . ?
C8 C9 C10 C11 -11.82(11) . . . . ?
C8 C9 C10 C20 168.97(11) . . . . ?
C8 C9 C14 O2 94.13(13) . . . . ?
C8 C9 C14 O3 -82.64(11) . . . . ?
C8 C9 C17 O4 -4.25(16) . . . . ?
C8 C9 C17 O5 174.01(9) . . . . ?
C9 C10 C11 N1 7.97(11) . . . . ?
C9 C10 C20 C21 178.15(10) . . . . ?
C10 C9 C14 O2 -16.54(15) . . . . ?
C10 C9 C14 O3 166.69(9) . . . . ?
C10 C9 C17 O4 113.66(13) . . . . ?
C10 C9 C17 O5 -68.08(12) . . . . ?
C10 C20 C21 O6 2.8(2) . . . . ?
C10 C20 C21 O7 -176.10(11) . . . . ?
C11 N1 C1 C2 3.3(2) . . . . ?
C11 N1 C1 C6 179.67(11) . . . . ?
C11 N1 C8 C7 179.91(9) . . . . ?
C11 N1 C8 C9 -7.20(13) . . . . ?
C11 C10 C20 C21 -0.94(19) . . . . ?
C12 O1 C4 C3 174.38(12) . . . . ?
C12 O1 C4 C5 -4.7(2) . . . . ?
C13 C7 C8 N1 -179.70(11) . . . . ?
C13 C7 C8 C9 10.8(2) . . . . ?
C14 O3 C15 C16 -176.18(12) . . . . ?
C14 C9 C10 C11 101.90(10) . . . . ?
C14 C9 C10 C20 -77.32(14) . . . . ?
C14 C9 C17 O4 -123.38(12) . . . . ?
C14 C9 C17 O5 54.88(12) . . . . ?
C15 O3 C14 O2 3.97(17) . . . . ?
C15 O3 C14 C9 -179.29(10) . . . . ?
C17 O5 C18 C19 -176.6(2) . . . . ?
C17 O5 C18 C19A 96.1(2) . . . . ?
C17 C9 C10 C11 -136.30(10) . . . . ?
C17 C9 C10 C20 44.48(15) . . . . ?
C17 C9 C14 O2 -142.24(12) . . . . ?
C17 C9 C14 O3 40.99(12) . . . . ?
C18 O5 C17 O4 3.29(18) . . . . ?
C18 O5 C17 C9 -174.96(11) . . . . ?
C20 C10 C11 N1 -172.83(11) . . . . ?
C22 O7 C21 O6 0.25(19) . . . . ?
C22 O7 C21 C20 179.20(12) . . . . ?

_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.647
####################################################################### 
# 
# 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_ahb-a-106
_database_code_depnum_ccdc_archive 'CCDC 2101460'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;CCART CREAIT Memorial University of Newfounland
Canada
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 N O7'
_chemical_formula_sum            'C23 H27 N O7'
_chemical_formula_weight         429.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H27NO7
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.27378(13)
_cell_length_b                   17.12971(15)
_cell_length_c                   9.94500(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.3152(10)
_cell_angle_gamma                90
_cell_volume                     2191.04(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10349
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1660
_cell_measurement_theta_min      3.4260
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19064
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.343
_diffrn_reflns_theta_min         3.436
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  26.00   0.50    0.08    --  -47.95  19.00 -60.00   76
  2  ω    -16.00  21.00   0.50    0.08    --  -47.95  19.00 -90.00   74
  3  ω    -43.00 -14.00   0.50    0.33    --  -86.25  45.00-150.00   58
  4  ω    -80.00   2.00   0.50    0.08    --  -47.95 100.00  35.00  164
  5  ω     31.00  58.00   0.50    0.08    --   47.95-100.00 -69.00   54
  6  ω     64.00 106.00   0.50    0.33    --  107.75-100.00 -69.00   84
  7  ω     81.00 106.00   0.50    0.33    --  107.75 -94.00 -30.00   50
  8  ω     50.00  78.00   0.50    0.33    --  107.75 -61.00 -60.00   56
  9  ω     35.00  60.00   0.50    0.33    --  107.75 -94.00 -30.00   50
 10  ω     46.00  79.00   0.50    0.33    --  107.75 -61.00 -30.00   66
 11  ω     37.00  71.00   0.50    0.33    --  107.75 -61.00  30.00   68
 12  ω     53.00  79.00   0.50    0.33    --  107.75 -61.00  60.00   52
 13  ω     39.00  79.00   0.50    0.33    --  107.75 -61.00  90.00   80
 14  ω     36.00  78.00   0.50    0.33    --  107.75 -61.00 150.00   84
 15  ω     36.00  76.00   0.50    0.33    --  107.75-125.00  90.00   80
 16  ω     83.00 110.00   0.50    0.33    --  107.75-125.00  90.00   54
 17  ω     39.00  65.00   0.50    0.33    --  107.75 -94.00  30.00   52
 18  ω     97.00 167.00   0.50    0.33    --  107.75  30.00  90.00  140
 19  ω    140.00 173.00   0.50    0.33    --  107.75  77.00 150.00   66
 20  ω    152.00 178.00   0.50    0.33    --  107.75 125.00  90.00   52
 21  ω    122.00 147.00   0.50    0.33    --  107.75 125.00  90.00   50
 22  ω    112.00 165.00   0.50    0.33    --  107.75 100.00  35.00  106
 23  ω    153.00 178.00   0.50    0.33    --  107.75  61.00 -30.00   50
 24  ω    149.00 174.00   0.50    0.33    --  107.75  61.00 -90.00   50
 25  ω    109.00 135.00   0.50    0.33    --  107.75  61.00 -90.00   52
 26  ω     97.00 143.00   0.50    0.33    --  107.75  61.00 -30.00   92
 27  ω     96.00 165.00   0.50    0.33    --  107.75 125.00  60.00  138
 28  ω     86.00 123.00   0.50    0.33    --  107.75  77.00 150.00   74
 29  ω    -13.00  27.00   0.50    0.08    --  -47.95  19.00 150.00   80
 30  ω    -71.00 -46.00   0.50    0.33    --  -86.25 100.00  35.00   50
 31  ω   -130.00-105.00   0.50    0.33    --  -86.25-100.00 -69.00   50
 32  ω   -120.00 -95.00   0.50    0.08    --  -47.95-125.00  60.00   50
 33  ω   -118.00 -73.00   0.50    0.08    --  -47.95-125.00  90.00   90
 34  ω     38.00  63.00   0.50    0.33    --  107.75 -61.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310449000
_diffrn_orient_matrix_UB_12      0.0817866000
_diffrn_orient_matrix_UB_13      0.0400679000
_diffrn_orient_matrix_UB_21      -0.1148065000
_diffrn_orient_matrix_UB_22      -0.0254190000
_diffrn_orient_matrix_UB_23      -0.0336460000
_diffrn_orient_matrix_UB_31      0.0140567000
_diffrn_orient_matrix_UB_32      -0.0274268000
_diffrn_orient_matrix_UB_33      0.1511267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3981
_reflns_number_total             4580
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00083(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.060
_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)+(0.0458P)²+0.6602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C)
;
_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 0.37993(8) 0.62286(6) 0.82149(9) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.39405(7) 0.45099(5) 0.38991(9) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.37889(7) 0.54964(5) 0.23637(9) 0.0202(2) Uani 1 1 d . . . . .
O4 O 0.14360(7) 0.58822(6) 0.08717(9) 0.0218(2) Uani 1 1 d . . . . .
O5 O 0.20275(7) 0.63127(5) 0.30601(9) 0.0192(2) Uani 1 1 d . . . . .
O6 O 0.13753(9) 0.30252(6) -0.05391(11) 0.0313(2) Uani 1 1 d . . . . .
O7 O 0.31147(9) 0.29411(6) -0.00461(13) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.09028(9) 0.41685(7) 0.52721(11) 0.0211(2) Uani 1 1 d . . . . .
C1 C 0.15795(10) 0.46675(8) 0.61521(13) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.17254(11) 0.47969(8) 0.75733(14) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.132074 0.452639 0.808894 0.027 Uiso 1 1 calc R U . . .
C3 C 0.24722(11) 0.53274(8) 0.82072(13) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.258711 0.542273 0.917433 0.028 Uiso 1 1 calc R U . . .
C4 C 0.30686(10) 0.57309(8) 0.74374(13) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.29186(10) 0.56157(7) 0.60227(13) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.331212 0.589969 0.550898 0.021 Uiso 1 1 calc R U . . .
C6 C 0.21696(10) 0.50684(7) 0.53682(13) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.18185(10) 0.47859(7) 0.39729(12) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.22217(10) 0.49647(7) 0.27061(12) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.18224(10) 0.43202(7) 0.16270(12) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.06821(10) 0.41483(8) 0.14137(14) 0.0223(3) Uani 1 1 d . . . . .
H10A H 0.045893 0.377503 0.063697 0.027 Uiso 1 1 calc R U . . .
H10B H 0.027883 0.463582 0.116325 0.027 Uiso 1 1 calc R U . . .
C11 C 0.04546(10) 0.38011(8) 0.27353(14) 0.0230(3) Uani 1 1 d . . . . .
H11A H -0.029921 0.383267 0.268045 0.028 Uiso 1 1 calc R U . . .
H11B H 0.066401 0.324513 0.282743 0.028 Uiso 1 1 calc R U . . .
C12 C 0.10490(10) 0.42497(7) 0.39586(13) 0.0190(3) Uani 1 1 d . . . . .
C13 C 0.01631(11) 0.36462(9) 0.56670(16) 0.0274(3) Uani 1 1 d . . . . .
H13A H -0.052969 0.388419 0.542501 0.041 Uiso 1 1 calc R U . . .
H13B H 0.037457 0.355239 0.666960 0.041 Uiso 1 1 calc R U . . .
H13C H 0.014534 0.314943 0.517274 0.041 Uiso 1 1 calc R U . . .
C14 C 0.43698(11) 0.67052(8) 0.74920(15) 0.0264(3) Uani 1 1 d . . . . .
H14A H 0.388919 0.704555 0.684240 0.040 Uiso 1 1 calc R U . . .
H14B H 0.474516 0.637294 0.697729 0.040 Uiso 1 1 calc R U . . .
H14C H 0.486775 0.702533 0.815863 0.040 Uiso 1 1 calc R U . . .
C15 C 0.34181(10) 0.49625(7) 0.30925(12) 0.0161(2) Uani 1 1 d . . . . .
C16 C 0.49162(10) 0.54803(9) 0.25349(15) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.512045 0.499494 0.213075 0.030 Uiso 1 1 calc R U . . .
H16B H 0.527696 0.549539 0.353295 0.030 Uiso 1 1 calc R U . . .
C17 C 0.52106(13) 0.61746(11) 0.1812(2) 0.0388(4) Uani 1 1 d . . . . .
H17A H 0.482349 0.616825 0.083527 0.058 Uiso 1 1 calc R U . . .
H17B H 0.595823 0.615982 0.186974 0.058 Uiso 1 1 calc R U . . .
H17C H 0.504368 0.665201 0.225481 0.058 Uiso 1 1 calc R U . . .
C18 C 0.18412(10) 0.57646(7) 0.20744(12) 0.0164(2) Uani 1 1 d . . . . .
C19 C 0.17494(11) 0.71079(7) 0.26086(13) 0.0208(3) Uani 1 1 d . . . . .
H19A H 0.100495 0.713798 0.211522 0.025 Uiso 1 1 calc R U . . .
H19B H 0.217012 0.728751 0.197344 0.025 Uiso 1 1 calc R U . . .
C20 C 0.19637(12) 0.76039(8) 0.38911(14) 0.0253(3) Uani 1 1 d . . . . .
H20A H 0.179309 0.814894 0.363227 0.038 Uiso 1 1 calc R U . . .
H20B H 0.270091 0.756384 0.437388 0.038 Uiso 1 1 calc R U . . .
H20C H 0.153718 0.742301 0.450514 0.038 Uiso 1 1 calc R U . . .
C21 C 0.24752(11) 0.39414(8) 0.10261(13) 0.0193(3) Uani 1 1 d . . . . .
H21 H 0.317342 0.412181 0.123480 0.023 Uiso 1 1 calc R U . . .
C22 C 0.22191(11) 0.32678(8) 0.00666(13) 0.0221(3) Uani 1 1 d . . . . .
C23 C 0.30083(17) 0.22650(12) -0.0941(3) 0.0625(7) Uani 1 1 d . . . . .
H23A H 0.257643 0.239884 -0.186174 0.094 Uiso 1 1 calc R U . . .
H23B H 0.267949 0.183999 -0.054510 0.094 Uiso 1 1 calc R U . . .
H23C H 0.369697 0.209800 -0.102197 0.094 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 C4 1.3764(17) . ?
O1 C14 1.4234(18) . ?
O2 C15 1.2042(16) . ?
O3 C15 1.3343(15) . ?
O3 C16 1.4638(15) . ?
O4 C18 1.2010(15) . ?
O5 C18 1.3355(15) . ?
O5 C19 1.4530(15) . ?
O6 C22 1.2068(18) . ?
O7 C22 1.3435(18) . ?
O7 C23 1.4459(19) . ?
N1 C1 1.3837(18) . ?
N1 C12 1.3744(17) . ?
N1 C13 1.4524(17) . ?
C1 C2 1.3960(19) . ?
C1 C6 1.4123(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.4108(19) . ?
C4 C5 1.3854(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4040(18) . ?
C6 C7 1.4343(17) . ?
C7 C8 1.5168(16) . ?
C7 C12 1.3711(18) . ?
C8 C9 1.5396(17) . ?
C8 C15 1.5388(17) . ?
C8 C18 1.5397(17) . ?
C9 C10 1.5046(18) . ?
C9 C21 1.3360(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5390(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.4894(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.491(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5001(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.4823(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C4 O1 C14 117.42(10) . . ?
C15 O3 C16 115.32(10) . . ?
C18 O5 C19 116.45(9) . . ?
C22 O7 C23 115.54(13) . . ?
C1 N1 C13 125.88(11) . . ?
C12 N1 C1 108.45(11) . . ?
C12 N1 C13 125.67(12) . . ?
N1 C1 C2 130.11(12) . . ?
N1 C1 C6 108.25(11) . . ?
C2 C1 C6 121.64(12) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.17(12) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.79(12) . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 114.24(11) . . ?
O1 C4 C5 124.27(12) . . ?
C5 C4 C3 121.48(13) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.26(12) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 106.15(11) . . ?
C5 C6 C1 119.64(11) . . ?
C5 C6 C7 134.21(11) . . ?
C6 C7 C8 129.68(11) . . ?
C12 C7 C6 107.40(11) . . ?
C12 C7 C8 122.79(11) . . ?
C7 C8 C9 107.63(10) . . ?
C7 C8 C15 110.27(10) . . ?
C7 C8 C18 111.78(10) . . ?
C9 C8 C18 109.39(10) . . ?
C15 C8 C9 109.18(10) . . ?
C15 C8 C18 108.56(10) . . ?
C10 C9 C8 113.55(11) . . ?
C21 C9 C8 120.69(12) . . ?
C21 C9 C10 125.66(12) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 110.99(11) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 108.79(11) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N1 C12 C11 123.60(12) . . ?
C7 C12 N1 109.74(11) . . ?
C7 C12 C11 126.65(12) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O3 125.04(12) . . ?
O2 C15 C8 123.82(11) . . ?
O3 C15 C8 111.05(10) . . ?
O3 C16 H16A 110.1 . . ?
O3 C16 H16B 110.1 . . ?
O3 C16 C17 108.13(12) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 124.69(12) . . ?
O4 C18 C8 125.21(11) . . ?
O5 C18 C8 110.09(10) . . ?
O5 C19 H19A 110.4 . . ?
O5 C19 H19B 110.4 . . ?
O5 C19 C20 106.74(10) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21 116.7 . . ?
C9 C21 C22 126.52(12) . . ?
C22 C21 H21 116.7 . . ?
O6 C22 O7 123.11(12) . . ?
O6 C22 C21 128.76(13) . . ?
O7 C22 C21 108.13(11) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C4 C5 C6 177.71(11) . . . . ?
N1 C1 C2 C3 179.17(13) . . . . ?
N1 C1 C6 C5 179.88(11) . . . . ?
N1 C1 C6 C7 -0.15(14) . . . . ?
C1 N1 C12 C7 0.76(15) . . . . ?
C1 N1 C12 C11 179.86(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C6 C7 C8 -175.26(12) . . . . ?
C1 C6 C7 C12 0.60(14) . . . . ?
C2 C1 C6 C5 -0.45(19) . . . . ?
C2 C1 C6 C7 179.53(12) . . . . ?
C2 C3 C4 O1 -178.63(12) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -1.57(19) . . . . ?
C4 C5 C6 C1 1.42(18) . . . . ?
C4 C5 C6 C7 -178.55(13) . . . . ?
C5 C6 C7 C8 4.7(2) . . . . ?
C5 C6 C7 C12 -179.43(14) . . . . ?
C6 C1 C2 C3 -0.43(19) . . . . ?
C6 C7 C8 C9 161.73(12) . . . . ?
C6 C7 C8 C15 42.73(17) . . . . ?
C6 C7 C8 C18 -78.13(16) . . . . ?
C6 C7 C12 N1 -0.84(14) . . . . ?
C6 C7 C12 C11 -179.91(12) . . . . ?
C7 C8 C9 C10 47.28(13) . . . . ?
C7 C8 C9 C21 -129.38(12) . . . . ?
C7 C8 C15 O2 38.17(16) . . . . ?
C7 C8 C15 O3 -145.14(10) . . . . ?
C7 C8 C18 O4 -129.63(13) . . . . ?
C7 C8 C18 O5 50.41(13) . . . . ?
C8 C7 C12 N1 175.37(11) . . . . ?
C8 C7 C12 C11 -3.7(2) . . . . ?
C8 C9 C10 C11 -65.50(14) . . . . ?
C8 C9 C21 C22 174.46(12) . . . . ?
C9 C8 C15 O2 -79.88(14) . . . . ?
C9 C8 C15 O3 96.81(12) . . . . ?
C9 C8 C18 O4 -10.53(17) . . . . ?
C9 C8 C18 O5 169.51(10) . . . . ?
C9 C10 C11 C12 43.36(14) . . . . ?
C9 C21 C22 O6 14.5(2) . . . . ?
C9 C21 C22 O7 -165.55(13) . . . . ?
C10 C9 C21 C22 -1.8(2) . . . . ?
C10 C11 C12 N1 169.88(12) . . . . ?
C10 C11 C12 C7 -11.18(18) . . . . ?
C12 N1 C1 C2 180.00(13) . . . . ?
C12 N1 C1 C6 -0.36(14) . . . . ?
C12 C7 C8 C9 -13.57(16) . . . . ?
C12 C7 C8 C15 -132.57(12) . . . . ?
C12 C7 C8 C18 106.57(13) . . . . ?
C13 N1 C1 C2 -0.1(2) . . . . ?
C13 N1 C1 C6 179.59(12) . . . . ?
C13 N1 C12 C7 -179.19(12) . . . . ?
C13 N1 C12 C11 -0.1(2) . . . . ?
C14 O1 C4 C3 -174.77(12) . . . . ?
C14 O1 C4 C5 5.90(19) . . . . ?
C15 O3 C16 C17 -172.38(12) . . . . ?
C15 C8 C9 C10 166.98(10) . . . . ?
C15 C8 C9 C21 -9.68(16) . . . . ?
C15 C8 C18 O4 108.52(14) . . . . ?
C15 C8 C18 O5 -71.44(12) . . . . ?
C16 O3 C15 O2 3.47(18) . . . . ?
C16 O3 C15 C8 -173.17(10) . . . . ?
C18 O5 C19 C20 176.46(11) . . . . ?
C18 C8 C9 C10 -74.36(13) . . . . ?
C18 C8 C9 C21 108.98(13) . . . . ?
C18 C8 C15 O2 160.93(11) . . . . ?
C18 C8 C15 O3 -22.38(13) . . . . ?
C19 O5 C18 O4 -2.48(18) . . . . ?
C19 O5 C18 C8 177.48(10) . . . . ?
C21 C9 C10 C11 110.96(14) . . . . ?
C23 O7 C22 O6 -0.6(2) . . . . ?
C23 O7 C22 C21 179.43(16) . . . . ?

_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.395
####################################################################### 
# 
# 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_nt-c-118-b-2
_database_code_depnum_ccdc_archive 'CCDC 2101462'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;CCART CREAIT Memorial University of Newfounland
Canada
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 N O5'
_chemical_formula_sum            'C25 H25 N O5'
_chemical_formula_weight         419.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2549(5)
_cell_length_b                   10.9358(4)
_cell_length_c                   11.8353(5)
_cell_angle_alpha                70.812(4)
_cell_angle_beta                 83.459(4)
_cell_angle_gamma                69.525(4)
_cell_volume                     1059.84(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8320
_cell_measurement_theta_min      3.9350
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.352
_diffrn_reflns_theta_min         3.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00 120.00   0.50    0.08    --   47.95  67.00 -62.00  182
  2  ω     85.00 178.00   0.50    0.32    --  107.75  77.00  60.00  186
  3  ω     87.00 177.00   0.50    0.32    --  107.75  77.00  30.00  180
  4  ω     96.00 121.00   0.50    0.32    --  107.75  30.00  30.00   50
  5  ω    132.00 173.00   0.50    0.32    --  107.75  15.00 -30.00   82
  6  ω     89.00 178.00   0.50    0.32    --  107.75  67.00 -62.00  178
  7  ω     94.00 178.00   0.50    0.32    --  107.75  15.00-120.00  168
  8  ω     95.00 178.00   0.50    0.32    --  107.75  45.00-180.00  166
  9  ω     93.00 149.00   0.50    0.32    --  107.75  61.00-150.00  112
 10  ω     36.00  66.00   0.50    0.32    --  107.75 -94.00  90.00   60
 11  ω     35.00 112.00   0.50    0.32    --  107.75-125.00 150.00  154
 12  ω     39.00  77.00   0.50    0.32    --  107.75-125.00  60.00   76
 13  ω     78.00 106.00   0.50    0.32    --  107.75 -94.00   0.00   56
 14  ω     34.00  96.00   0.50    0.08    --   47.95-125.00   0.00  124
 15  ω     35.00  66.00   0.50    0.32    --  107.75 -94.00   0.00   62
 16  ω     36.00 106.00   0.50    0.32    --  107.75 -94.00 -60.00  140
 17  ω     82.00 107.00   0.50    0.32    --  107.75-104.00 -82.80   50
 18  ω     44.00  69.00   0.50    0.32    --  107.75-104.00 -82.80   50
 19  ω     66.00 105.00   0.50    0.32    --  107.75 -94.00-150.00   78
 20  ω     34.00  96.00   0.50    0.08    --   47.95-125.00-180.00  124
 21  ω     54.00 106.00   0.50    0.32    --  107.75 -94.00-180.00  104
 22  ω     58.00 104.00   0.50    0.32    --  107.75 -94.00 -30.00   92
 23  ω     80.00 105.00   0.50    0.32    --  107.75 -94.00  30.00   50
 24  ω     70.00 105.00   0.50    0.32    --  107.75 -94.00  90.00   70
 25  ω     35.00 106.00   0.50    0.32    --  107.75 -94.00  60.00  142
 26  ω     49.00  97.00   0.50    0.32    --  107.75 -94.00 120.00   96
 27  ω     44.00 105.00   0.50    0.32    --  107.75 -94.00 150.00  122
 28  ω    -24.00  67.00   0.50    0.08    --   47.95 -67.00 163.00  182
 29  ω     35.00  89.00   0.50    0.32    --  107.75 -67.00 163.00  108
 30  ω     35.00  60.00   0.50    0.32    --  107.75 -61.00  90.00   50
 31  ω    -26.00  30.00   0.50    0.08    --   47.95 -19.00-120.00  112
 32  ω     51.00  79.00   0.50    0.32    --  107.75 -61.00 -30.00   56
 33  ω     37.00  64.00   0.50    0.32    --  107.75 -61.00 -60.00   54
 34  ω     37.00  73.00   0.50    0.32    --  107.75 -61.00-150.00   72
 35  ω     95.00 138.00   0.50    0.32    --  107.75 125.00  30.00   86
 36  ω    146.00 175.00   0.50    0.32    --  107.75 125.00  30.00   58
 37  ω     96.00 147.00   0.50    0.32    --  107.75 125.00-120.00  102
 38  ω    -67.00  25.00   0.50    0.08    --  -47.95  67.00 -62.00  184
 39  ω    -75.00 -13.00   0.50    0.32    --  -86.25  67.00 -62.00  124
 40  ω    -43.00 -14.00   0.50    0.32    --  -86.25  45.00  60.00   58
 41  ω    -43.00 -14.00   0.50    0.32    --  -86.25  45.00  90.00   58
 42  ω    -43.00 -14.00   0.50    0.32    --  -86.25  45.00 120.00   58
 43  ω   -120.00 -29.00   0.50    0.08    --  -47.95 -67.00 163.00  182
 44  ω   -159.00 -67.00   0.50    0.32    --  -86.25 -67.00 163.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1523264000
_diffrn_orient_matrix_UB_12      0.0450444000
_diffrn_orient_matrix_UB_13      -0.0671253000
_diffrn_orient_matrix_UB_21      0.0321439000
_diffrn_orient_matrix_UB_22      0.1300647000
_diffrn_orient_matrix_UB_23      -0.0817275000
_diffrn_orient_matrix_UB_31      0.0856460000
_diffrn_orient_matrix_UB_32      -0.0779446000
_diffrn_orient_matrix_UB_33      -0.0883746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3765
_reflns_number_total             4403
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.3185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_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 0.49807(13) 0.66141(12) 0.64363(9) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.32741(13) 0.58349(11) 0.77002(9) 0.0329(3) Uani 1 1 d . . . . .
O3 O 0.19222(12) 0.47576(11) 0.45546(9) 0.0317(2) Uani 1 1 d . . . . .
O4 O 0.14090(12) 0.56005(10) 0.25882(9) 0.0300(2) Uani 1 1 d . . . . .
O5 O 0.70979(12) 0.89425(12) -0.17063(9) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.44841(13) 0.72200(12) 0.26753(10) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.45517(16) 0.69229(14) 0.39214(12) 0.0256(3) Uani 1 1 d . . . . .
H1 H 0.541677 0.682274 0.434808 0.031 Uiso 1 1 calc R U . . .
C2 C 0.32117(16) 0.68021(14) 0.44169(12) 0.0252(3) Uani 1 1 d . . . . .
C3 C 0.21024(15) 0.70075(14) 0.34368(12) 0.0241(3) Uani 1 1 d . . . . .
C4 C 0.30371(15) 0.73797(14) 0.23208(12) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.29065(16) 0.78679(14) 0.11074(12) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.43711(16) 0.80282(14) 0.06721(12) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.49230(16) 0.84842(14) -0.04922(12) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.429235 0.876008 -0.117157 0.031 Uiso 1 1 calc R U . . .
C8 C 0.64130(17) 0.85185(15) -0.06173(13) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.73549(17) 0.81175(16) 0.03808(13) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.837218 0.815706 0.026001 0.036 Uiso 1 1 calc R U . . .
C10 C 0.68360(16) 0.76666(15) 0.15353(13) 0.0286(3) Uani 1 1 d . . . . .
H10 H 0.747512 0.739382 0.220911 0.034 Uiso 1 1 calc R U . . .
C11 C 0.53336(16) 0.76300(14) 0.16666(12) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.27022(17) 0.65098(16) 0.56894(12) 0.0295(3) Uani 1 1 d . . . . .
H12A H 0.243151 0.566106 0.591448 0.035 Uiso 1 1 calc R U . . .
H12B H 0.174510 0.726644 0.573906 0.035 Uiso 1 1 calc R U . . .
C13 C 0.38089(17) 0.63369(14) 0.66079(12) 0.0272(3) Uani 1 1 d . . . . .
C14 C 0.4238(2) 0.55695(17) 0.86856(13) 0.0371(4) Uani 1 1 d . . . . .
H14A H 0.528442 0.498714 0.856592 0.056 Uiso 1 1 calc R U . . .
H14B H 0.381724 0.510035 0.943318 0.056 Uiso 1 1 calc R U . . .
H14C H 0.426752 0.644022 0.872829 0.056 Uiso 1 1 calc R U . . .
C15 C 0.18284(15) 0.56474(14) 0.36068(12) 0.0252(3) Uani 1 1 d . . . . .
C16 C 0.1073(2) 0.43663(17) 0.26804(14) 0.0350(3) Uani 1 1 d . . . . .
H16A H 0.018471 0.430137 0.322041 0.042 Uiso 1 1 calc R U . . .
H16B H 0.197580 0.354010 0.300675 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0703(2) 0.44619(19) 0.14487(16) 0.0426(4) Uani 1 1 d . . . . .
H17A H 0.159985 0.449999 0.092835 0.064 Uiso 1 1 calc R U . . .
H17B H -0.017681 0.529393 0.112817 0.064 Uiso 1 1 calc R U . . .
H17C H 0.044524 0.365420 0.148343 0.064 Uiso 1 1 calc R U . . .
C18 C 0.05363(15) 0.81196(14) 0.34730(11) 0.0246(3) Uani 1 1 d . . . . .
C19 C -0.07013(16) 0.77680(15) 0.41041(12) 0.0272(3) Uani 1 1 d . . . . .
H19 H -0.060052 0.682884 0.447639 0.033 Uiso 1 1 calc R U . . .
C20 C -0.20845(17) 0.87862(17) 0.41917(13) 0.0323(3) Uani 1 1 d . . . . .
H20 H -0.292192 0.853717 0.462431 0.039 Uiso 1 1 calc R U . . .
C21 C -0.22483(18) 1.01532(17) 0.36554(14) 0.0348(3) Uani 1 1 d . . . . .
H21 H -0.319179 1.084551 0.372117 0.042 Uiso 1 1 calc R U . . .
C22 C -0.10191(19) 1.05111(16) 0.30162(13) 0.0330(3) Uani 1 1 d . . . . .
H22 H -0.112669 1.145134 0.264174 0.040 Uiso 1 1 calc R U . . .
C23 C 0.03662(17) 0.94974(15) 0.29237(12) 0.0287(3) Uani 1 1 d . . . . .
H23 H 0.119836 0.974848 0.248337 0.034 Uiso 1 1 calc R U . . .
C24 C 0.15468(16) 0.81953(16) 0.03570(12) 0.0289(3) Uani 1 1 d . . . . .
H24A H 0.147143 0.901914 -0.032620 0.043 Uiso 1 1 calc R U . . .
H24B H 0.060534 0.835965 0.083813 0.043 Uiso 1 1 calc R U . . .
H24C H 0.167142 0.742189 0.006673 0.043 Uiso 1 1 calc R U . . .
C25 C 0.62050(19) 0.93459(18) -0.27471(13) 0.0348(3) Uani 1 1 d . . . . .
H25A H 0.680738 0.963125 -0.345929 0.052 Uiso 1 1 calc R U . . .
H25B H 0.526570 1.011420 -0.272545 0.052 Uiso 1 1 calc R U . . .
H25C H 0.592543 0.857083 -0.277513 0.052 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 C13 1.2036(19) . ?
O2 C13 1.3399(17) . ?
O2 C14 1.4398(18) . ?
O3 C15 1.2076(17) . ?
O4 C15 1.3296(17) . ?
O4 C16 1.4560(18) . ?
O5 C8 1.3801(16) . ?
O5 C25 1.419(2) . ?
N1 C1 1.4058(17) . ?
N1 C4 1.3843(18) . ?
N1 C11 1.3876(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3406(19) . ?
C2 C3 1.5456(19) . ?
C2 C12 1.4899(18) . ?
C3 C4 1.5137(18) . ?
C3 C15 1.540(2) . ?
C3 C18 1.5391(19) . ?
C4 C5 1.3610(19) . ?
C5 C6 1.4425(18) . ?
C5 C24 1.4936(19) . ?
C6 C7 1.4052(18) . ?
C6 C11 1.4139(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(2) . ?
C8 C9 1.405(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.500(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.497(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3936(19) . ?
C18 C23 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(2) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C13 O2 C14 115.69(12) . . ?
C15 O4 C16 115.00(11) . . ?
C8 O5 C25 117.02(12) . . ?
C4 N1 C1 111.14(11) . . ?
C4 N1 C11 108.88(11) . . ?
C11 N1 C1 138.82(12) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 N1 109.77(12) . . ?
C2 C1 H1 125.1 . . ?
C1 C2 C3 109.81(11) . . ?
C1 C2 C12 130.59(13) . . ?
C12 C2 C3 119.60(12) . . ?
C4 C3 C2 100.96(11) . . ?
C4 C3 C15 111.28(11) . . ?
C4 C3 C18 114.16(11) . . ?
C15 C3 C2 109.61(11) . . ?
C18 C3 C2 111.89(11) . . ?
C18 C3 C15 108.74(11) . . ?
N1 C4 C3 107.86(11) . . ?
C5 C4 N1 110.80(12) . . ?
C5 C4 C3 141.26(13) . . ?
C4 C5 C6 105.59(12) . . ?
C4 C5 C24 128.36(12) . . ?
C6 C5 C24 126.05(12) . . ?
C7 C6 C5 131.79(13) . . ?
C7 C6 C11 119.81(13) . . ?
C11 C6 C5 108.41(11) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.87(13) . . ?
C8 C7 H7 121.1 . . ?
O5 C8 C7 123.85(14) . . ?
O5 C8 C9 114.56(13) . . ?
C7 C8 C9 121.59(13) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.57(13) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 121.5 . . ?
C9 C10 C11 117.08(13) . . ?
C11 C10 H10 121.5 . . ?
N1 C11 C6 106.32(12) . . ?
N1 C11 C10 131.58(13) . . ?
C10 C11 C6 122.09(12) . . ?
C2 C12 H12A 107.9 . . ?
C2 C12 H12B 107.9 . . ?
C2 C12 C13 117.76(12) . . ?
H12A C12 H12B 107.2 . . ?
C13 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
O1 C13 O2 123.49(14) . . ?
O1 C13 C12 127.58(13) . . ?
O2 C13 C12 108.91(12) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 124.11(13) . . ?
O3 C15 C3 124.33(13) . . ?
O4 C15 C3 111.50(11) . . ?
O4 C16 H16A 110.2 . . ?
O4 C16 H16B 110.2 . . ?
O4 C16 C17 107.47(13) . . ?
H16A C16 H16B 108.5 . . ?
C17 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C3 120.74(12) . . ?
C23 C18 C3 120.01(12) . . ?
C23 C18 C19 119.16(13) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.32(14) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.49(14) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.46(14) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.31(14) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.24(13) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C5 C24 H24A 109.5 . . ?
C5 C24 H24B 109.5 . . ?
C5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O5 C8 C9 C10 179.99(13) . . . . ?
N1 C1 C2 C3 1.06(16) . . . . ?
N1 C1 C2 C12 -179.38(14) . . . . ?
N1 C4 C5 C6 -0.15(15) . . . . ?
N1 C4 C5 C24 -179.50(13) . . . . ?
C1 N1 C4 C3 -6.57(15) . . . . ?
C1 N1 C4 C5 170.82(12) . . . . ?
C1 N1 C11 C6 -166.87(15) . . . . ?
C1 N1 C11 C10 14.3(3) . . . . ?
C1 C2 C3 C4 -4.65(15) . . . . ?
C1 C2 C3 C15 112.83(13) . . . . ?
C1 C2 C3 C18 -126.46(13) . . . . ?
C1 C2 C12 C13 1.3(2) . . . . ?
C2 C3 C4 N1 6.56(14) . . . . ?
C2 C3 C4 C5 -169.53(18) . . . . ?
C2 C3 C15 O3 26.90(18) . . . . ?
C2 C3 C15 O4 -155.85(11) . . . . ?
C2 C3 C18 C19 -94.22(15) . . . . ?
C2 C3 C18 C23 82.49(15) . . . . ?
C2 C12 C13 O1 12.7(2) . . . . ?
C2 C12 C13 O2 -168.63(12) . . . . ?
C3 C2 C12 C13 -179.19(12) . . . . ?
C3 C4 C5 C6 175.87(17) . . . . ?
C3 C4 C5 C24 -3.5(3) . . . . ?
C3 C18 C19 C20 176.13(13) . . . . ?
C3 C18 C23 C22 -176.04(13) . . . . ?
C4 N1 C1 C2 3.52(16) . . . . ?
C4 N1 C11 C6 -0.96(15) . . . . ?
C4 N1 C11 C10 -179.76(15) . . . . ?
C4 C3 C15 O3 137.72(14) . . . . ?
C4 C3 C15 O4 -45.03(15) . . . . ?
C4 C3 C18 C19 151.90(13) . . . . ?
C4 C3 C18 C23 -31.39(18) . . . . ?
C4 C5 C6 C7 179.68(14) . . . . ?
C4 C5 C6 C11 -0.46(15) . . . . ?
C5 C6 C7 C8 -179.85(14) . . . . ?
C5 C6 C11 N1 0.87(15) . . . . ?
C5 C6 C11 C10 179.81(13) . . . . ?
C6 C7 C8 O5 179.96(13) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C6 C11 N1 -179.24(12) . . . . ?
C7 C6 C11 C10 -0.3(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 N1 178.86(14) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C11 N1 C1 C2 169.22(16) . . . . ?
C11 N1 C4 C3 -176.67(11) . . . . ?
C11 N1 C4 C5 0.71(16) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
C12 C2 C3 C4 175.73(12) . . . . ?
C12 C2 C3 C15 -66.79(16) . . . . ?
C12 C2 C3 C18 53.92(16) . . . . ?
C14 O2 C13 O1 -3.2(2) . . . . ?
C14 O2 C13 C12 178.15(12) . . . . ?
C15 O4 C16 C17 -177.19(13) . . . . ?
C15 C3 C4 N1 -109.70(13) . . . . ?
C15 C3 C4 C5 74.2(2) . . . . ?
C15 C3 C18 C19 26.99(17) . . . . ?
C15 C3 C18 C23 -156.29(12) . . . . ?
C16 O4 C15 O3 -0.6(2) . . . . ?
C16 O4 C15 C3 -177.89(11) . . . . ?
C18 C3 C4 N1 126.76(12) . . . . ?
C18 C3 C4 C5 -49.3(2) . . . . ?
C18 C3 C15 O3 -95.70(15) . . . . ?
C18 C3 C15 O4 81.55(13) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C18 C23 C22 0.7(2) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C20 C21 C22 C23 -0.3(2) . . . . ?
C21 C22 C23 C18 -0.3(2) . . . . ?
C23 C18 C19 C20 -0.6(2) . . . . ?
C24 C5 C6 C7 -1.0(2) . . . . ?
C24 C5 C6 C11 178.92(13) . . . . ?
C25 O5 C8 C7 -0.8(2) . . . . ?
C25 O5 C8 C9 179.35(13) . . . . ?

_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.736
