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

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

data_caohn_0825_auto
_audit_block_doi                 10.5517/ccdc.csd.cc29wc5r
_database_code_depnum_ccdc_archive 'CCDC 2141454'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;LanZhou University
China
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
'(1R,2R,3R,4R,5S,6S)-6-hydroxy-6-(2-(pyridin-2-yl)ethyl)cyclohexane-1,2,3,4,5-pentayl pentaacetate'
_chemical_formula_moiety         'C23 H29 N O11'
_chemical_formula_sum            'C23 H29 N O11'
_chemical_formula_weight         495.47
_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                   9.59580(9)
_cell_length_b                   11.62912(10)
_cell_length_c                   11.80883(10)
_cell_angle_alpha                96.0575(7)
_cell_angle_beta                 90.7961(7)
_cell_angle_gamma                107.8097(8)
_cell_volume                     1246.12(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    28120
_cell_measurement_temperature    294.4(6)
_cell_measurement_theta_max      76.3820
_cell_measurement_theta_min      3.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35365
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.235
_diffrn_reflns_theta_min         3.769
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.4(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  56.00   0.50    0.05    --   46.32  74.00 -26.00   56
  2  ω     25.00  51.00   0.50    0.05    --   46.32  77.00-120.00   52
  3  ω     60.00  87.00   0.50    0.05    --   46.32  74.00 -26.00   54
  4  ω     28.00  54.00   0.50    0.05    --   50.00  76.00  12.01   52
  5  ω     27.00  53.00   0.50    0.05    --   46.32  77.00 150.00   52
  6  ω     34.00  63.00   0.50    0.05    --   46.32  37.00  90.00   58
  7  ω     79.00 115.00   0.50    0.05    --  104.25-132.00 152.81   72
  8  ω     41.00  84.00   0.50    0.05    --  104.25-125.00  90.00   86
  9  ω     42.00  72.00   0.50    0.05    --  104.25-125.00  30.00   60
 10  ω     38.00 104.00   0.50    0.05    --  104.25-125.00 120.00  132
 11  ω     33.00 102.00   0.50    0.05    --  104.25 -94.00 120.00  138
 12  ω     79.00 111.00   0.50    0.05    --  104.25-125.00  30.00   64
 13  ω     39.00 112.00   0.50    0.05    --  104.25-125.00   0.00  146
 14  ω     35.00 111.00   0.50    0.05    --  104.25-125.00-120.00  152
 15  ω     74.00 101.00   0.50    0.05    --  104.25 -94.00-150.00   54
 16  ω    -21.00  68.00   0.50    0.05    --   46.32 -74.00-154.00  178
 17  ω     35.00  63.00   0.50    0.05    --  104.25 -61.00-120.00   56
 18  ω     63.00  91.00   0.50    0.05    --  104.25 -74.00-154.00   56
 19  ω     48.00  73.00   0.50    0.05    --  104.25 -61.00 -30.00   50
 20  ω     32.00  67.00   0.50    0.05    --  104.25 -61.00   0.00   70
 21  ω     48.00  73.00   0.50    0.05    --  104.25 -61.00  30.00   50
 22  ω     31.00  60.00   0.50    0.05    --   54.00  77.00-104.89   58
 23  ω     47.00  73.00   0.50    0.05    --   70.00  77.00-164.14   52
 24  ω     31.00  76.00   0.50    0.05    --   54.00  77.00  16.79   90
 25  ω     35.00  61.00   0.50    0.05    --   58.00  77.00  46.06   52
 26  ω     44.00  69.00   0.50    0.05    --   66.00  76.00  64.25   50
 27  ω     36.00  62.00   0.50    0.05    --   54.00  75.00 119.29   52
 28  ω     93.00 126.00   0.50    0.05    --   54.00  75.00 119.29   66
 29  ω     33.00  58.00   0.50    0.05    --   54.00  74.00 173.31   50
 30  ω    139.00 165.00   0.50    0.05    --  104.25  74.00 -26.00   52
 31  ω     87.00 134.00   0.50    0.05    --  104.25  74.00 -26.00   94
 32  ω     82.00 126.00   0.50    0.05    --   54.00  75.00-155.25   88
 33  ω     35.00  61.00   0.50    0.05    --   54.00  75.00-155.25   52
 34  ω     38.00  72.00   0.50    0.05    --   58.00  75.00 -84.45   68
 35  ω     33.00  58.00   0.50    0.05    --   54.00  73.00  93.20   50
 36  ω      7.00  40.00   0.50    0.05    --   30.00  87.00 119.92   66
 37  ω      9.00  34.00   0.50    0.05    --   38.00  91.00  31.17   50
 38  ω     -7.00  19.00   0.50    0.05    --   26.00 100.00 -39.73   52
 39  ω     14.00  39.00   0.50    0.05    --   42.00  89.00 -79.04   50
 40  ω    -14.00  11.00   0.50    0.05    --   18.00  98.00-162.76   50
 41  ω    -16.00  25.00   0.50    0.05    --  -46.32  74.00 -26.00   82
 42  ω    -63.00 -31.00   0.50    0.05    --  -46.32  74.00 -26.00   64
 43  ω    -90.00 -55.00   0.50    0.05    -- -102.00  74.00 -26.00   70
 44  ω    -69.00 -32.00   0.50    0.05    -- -102.00  61.00-180.00   74
 45  ω   -118.00 -84.00   0.50    0.05    --  -46.32 -19.00 -30.00   68
 46  ω    -79.00 -43.00   0.50    0.05    --  -46.32 -19.00 -30.00   72
 47  ω    -60.00 -34.00   0.50    0.05    --  -46.32 -37.00  60.00   52
 48  ω   -112.00 -55.00   0.50    0.05    -- -102.00 125.00 -90.00  114
 49  ω   -122.00 -37.00   0.50    0.05    -- -102.00 139.00 112.44  170
 50  ω    -50.00 -25.00   0.50    0.05    --  -46.32 -74.00-154.00   50
 51  ω   -174.00 -82.00   0.50    0.05    -- -102.00 -79.00 -98.41  184
 52  ω   -142.00-116.00   0.50    0.05    --  -70.00 -77.00-121.84   52
 53  ω    -73.00 -47.00   0.50    0.05    --  -70.00 -77.00-121.84   52
 54  ω    -76.00 -51.00   0.50    0.05    --  -74.00 -77.00 -97.47   50
 55  ω   -128.00 -79.00   0.50    0.05    -- -102.00 -77.00 -29.12   98
 56  ω    -72.00 -47.00   0.50    0.05    --  -70.00 -77.00   1.06   50
 57  ω    -72.00 -47.00   0.50    0.05    --  -70.00 -76.00  74.15   50
 58  ω    -70.00 -43.00   0.50    0.05    --  -66.00 -77.00 111.25   54
 59  ω    -97.00 -68.00   0.50    0.05    --  -90.00 -76.00 156.02   58
 60  ω   -160.00-113.00   0.50    0.05    --  -90.00 -76.00 156.02   94
 61  ω   -139.00-114.00   0.50    0.05    --  -66.00 -77.00 111.25   50
 62  ω   -104.00 -76.00   0.50    0.05    --  -98.00 -76.00 100.30   56
 63  ω   -121.00 -71.00   0.50    0.05    --  -94.00 -76.00  58.13  100
 64  ω   -170.00-109.00   0.50    0.05    --  -98.00 -76.00 100.30  122
 65  ω   -140.00-115.00   0.50    0.05    --  -70.00 -76.00  74.15   50
 66  ω   -140.00-114.00   0.50    0.05    --  -70.00 -76.00 142.04   52
 67  ω   -113.00 -71.00   0.50    0.05    --  -94.00 -76.00  12.07   84
 68  ω   -145.00 -79.00   0.50    0.05    -- -102.00 -76.00 -46.45  132
 69  ω   -174.00-131.00   0.50    0.05    -- -102.00 -77.00 -29.12   86
 70  ω   -153.00 -71.00   0.50    0.05    --  -94.00 -76.00-167.78  164
 71  ω    -81.00 -56.00   0.50    0.05    --  -78.00 -75.00 -20.40   50
 72  ω    -87.00 -61.00   0.50    0.05    --  -82.00 -73.00 -54.56   52
 73  ω   -168.00-139.00   0.50    0.05    -- -102.00 -74.00-154.00   58
 74  ω    -99.00 -61.00   0.50    0.05    --  -82.00 -73.00 -39.05   76
 75  ω    -89.00 -64.00   0.50    0.05    --  -86.00 -74.00   0.52   50
 76  ω    -95.00 -70.00   0.50    0.05    --  -90.00 -73.00 114.17   50
 77  ω    -72.00 -47.00   0.50    0.05    --  -70.00 -76.00 142.04   50
 78  ω    -86.00 -61.00   0.50    0.05    --  -82.00 -73.00 113.91   50
 79  ω    -90.00 -65.00   0.50    0.05    --  -86.00 -73.00  61.11   50
 80  ω    -93.00 -65.00   0.50    0.05    --  -86.00 -74.00  27.49   56
 81  ω   -136.00-110.00   0.50    0.05    --  -86.00 -73.00  61.11   52
 82  ω   -149.00-121.00   0.50    0.05    --  -90.00 -72.00 129.71   56
 83  ω   -162.00 -99.00   0.50    0.05    --  -90.00 -72.00  38.19  126
 84  ω   -114.00 -69.00   0.50    0.05    --  -90.00 -72.00 129.71   90
 85  ω   -102.00 -69.00   0.50    0.05    --  -90.00 -72.00-134.05   66
 86  ω    -87.00 -61.00   0.50    0.05    --  -82.00 -73.00-159.05   52
 87  ω   -132.00 -69.00   0.50    0.05    --  -90.00 -72.00-163.36  126
 88  ω   -161.00-114.00   0.50    0.05    --  -90.00 -72.00-134.05   94
 89  ω   -139.00 -72.00   0.50    0.05    --  -90.00 -72.00 -81.11  134
 90  ω    -89.00 -50.00   0.50    0.05    --  -70.00 -70.00 -82.42   78
 91  ω   -142.00 -95.00   0.50    0.05    --  -70.00 -70.00 -82.42   94
 92  ω    -75.00 -50.00   0.50    0.05    --  -70.00 -69.00 -63.74   50
 93  ω    -94.00 -69.00   0.50    0.05    --  -90.00 -72.00  38.19   50
 94  ω   -162.00-113.00   0.50    0.05    --  -90.00 -68.00 -18.19   98
 95  ω   -175.00-116.00   0.50    0.05    -- -102.00 -68.00  88.29  118
 96  ω   -127.00 -82.00   0.50    0.05    -- -102.00 -70.00 113.78   90
 97  ω   -155.00 -69.00   0.50    0.05    --  -90.00 -72.00 168.27  172
 98  ω   -165.00 -78.00   0.50    0.05    --  -98.00 -71.00 147.94  174
 99  ω   -102.00 -71.00   0.50    0.05    --  -90.00 -68.00 -18.19   62
100  ω    -89.00 -63.00   0.50    0.05    --  -82.00 -67.00-114.48   52
101  ω    -82.00 -55.00   0.50    0.05    --  -74.00 -67.00-160.05   54
102  ω   -153.00-125.00   0.50    0.05    --  -82.00 -67.00-114.48   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1345989000
_diffrn_orient_matrix_UB_12      0.0458618000
_diffrn_orient_matrix_UB_13      0.0007622000
_diffrn_orient_matrix_UB_21      -0.0504621000
_diffrn_orient_matrix_UB_22      -0.0618493000
_diffrn_orient_matrix_UB_23      0.1079115000
_diffrn_orient_matrix_UB_31      0.0885437000
_diffrn_orient_matrix_UB_32      0.1170166000
_diffrn_orient_matrix_UB_33      0.0748760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4639
_reflns_number_total             4922
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0109(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.052
_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)+(0.0520P)²+0.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1191
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.66004(11) 0.63050(10) 0.87719(8) 0.0445(3) Uani 1 1 d . . . . .
H1 H 0.631468 0.641151 0.941410 0.067 Uiso 1 1 calc R U . . .
O2 O 0.39347(11) 0.68385(9) 0.91361(8) 0.0455(3) Uani 1 1 d . . . . .
O3 O 0.16277(14) 0.57909(15) 0.85030(13) 0.0777(4) Uani 1 1 d . . . . .
O4 O 0.45197(11) 0.87628(9) 0.78110(9) 0.0444(3) Uani 1 1 d . . . . .
O5 O 0.63065(14) 1.01580(12) 0.89074(14) 0.0761(4) Uani 1 1 d . . . . .
O6 O 0.66517(12) 0.89730(9) 0.62067(9) 0.0502(3) Uani 1 1 d . . . . .
O7 O 0.5646(2) 0.84472(16) 0.44424(13) 0.1104(7) Uani 1 1 d . . . . .
O8 O 0.81301(10) 0.75488(10) 0.70824(8) 0.0471(3) Uani 1 1 d . . . . .
O9 O 0.95082(17) 0.7326(2) 0.56410(14) 0.1168(8) Uani 1 1 d . . . . .
O10 O 0.70104(12) 0.50457(10) 0.68707(8) 0.0478(3) Uani 1 1 d . . . . .
O11 O 0.67446(15) 0.44722(12) 0.49896(10) 0.0632(3) Uani 1 1 d . . . . .
N1 N 0.22803(15) 0.26660(12) 0.90140(11) 0.0498(3) Uani 1 1 d . . . . .
C1 C 0.53759(14) 0.58184(12) 0.79866(11) 0.0360(3) Uani 1 1 d . . . . .
C2 C 0.44532(14) 0.66987(12) 0.80041(11) 0.0370(3) Uani 1 1 d . . . . .
H2 H 0.361932 0.637073 0.744968 0.044 Uiso 1 1 calc R U . . .
C3 C 0.53871(15) 0.79457(12) 0.77324(12) 0.0378(3) Uani 1 1 d . . . . .
H3 H 0.625134 0.826105 0.825897 0.045 Uiso 1 1 calc R U . . .
C4 C 0.58458(15) 0.77940(12) 0.65147(12) 0.0393(3) Uani 1 1 d . . . . .
H4 H 0.496914 0.744505 0.600478 0.047 Uiso 1 1 calc R U . . .
C5 C 0.67986(15) 0.69673(13) 0.63955(11) 0.0397(3) Uani 1 1 d . . . . .
H5 H 0.703299 0.684437 0.559558 0.048 Uiso 1 1 calc R U . . .
C6 C 0.60046(15) 0.57392(12) 0.68014(11) 0.0374(3) Uani 1 1 d . . . . .
H6 H 0.520402 0.529243 0.624584 0.045 Uiso 1 1 calc R U . . .
C7 C 0.44679(16) 0.45651(13) 0.82873(12) 0.0420(3) Uani 1 1 d . . . . .
H7A H 0.513168 0.409947 0.840101 0.050 Uiso 1 1 calc R U . . .
H7B H 0.403155 0.467963 0.900968 0.050 Uiso 1 1 calc R U . . .
C8 C 0.32518(18) 0.38067(13) 0.74287(13) 0.0475(4) Uani 1 1 d . . . . .
H8A H 0.278535 0.434015 0.711041 0.057 Uiso 1 1 calc R U . . .
H8B H 0.368269 0.343717 0.680955 0.057 Uiso 1 1 calc R U . . .
C9 C 0.20971(16) 0.28183(12) 0.79277(12) 0.0416(3) Uani 1 1 d . . . . .
C10 C 0.0873(2) 0.20973(17) 0.72687(16) 0.0635(5) Uani 1 1 d . . . . .
H10 H 0.077417 0.219584 0.650346 0.076 Uiso 1 1 calc R U . . .
C11 C -0.0197(2) 0.1234(2) 0.77548(19) 0.0742(6) Uani 1 1 d . . . . .
H11 H -0.102764 0.075033 0.732386 0.089 Uiso 1 1 calc R U . . .
C12 C -0.0021(2) 0.10974(17) 0.88779(17) 0.0646(5) Uani 1 1 d . . . . .
H12 H -0.073055 0.052826 0.923053 0.078 Uiso 1 1 calc R U . . .
C13 C 0.12256(19) 0.18215(17) 0.94658(15) 0.0593(4) Uani 1 1 d . . . . .
H13 H 0.135074 0.172225 1.022784 0.071 Uiso 1 1 calc R U . . .
C14 C 0.24786(18) 0.63250(16) 0.92745(15) 0.0524(4) Uani 1 1 d . . . . .
C15 C 0.2122(2) 0.6495(2) 1.04941(18) 0.0766(6) Uani 1 1 d . . . . .
H15A H 0.242314 0.593707 1.090851 0.115 Uiso 1 1 calc R U . . .
H15B H 0.108534 0.634443 1.054375 0.115 Uiso 1 1 calc R U . . .
H15C H 0.262959 0.731354 1.081506 0.115 Uiso 1 1 calc R U . . .
C16 C 0.51309(18) 0.98635(14) 0.84243(14) 0.0496(4) Uani 1 1 d . . . . .
C17 C 0.4149(2) 1.06367(17) 0.84069(19) 0.0698(5) Uani 1 1 d . . . . .
H17A H 0.412024 1.089173 0.766217 0.105 Uiso 1 1 calc R U . . .
H17B H 0.451511 1.133843 0.895998 0.105 Uiso 1 1 calc R U . . .
H17C H 0.317937 1.017842 0.858742 0.105 Uiso 1 1 calc R U . . .
C18 C 0.6442(2) 0.91809(18) 0.51314(16) 0.0697(5) Uani 1 1 d . . . . .
C19 C 0.7368(4) 1.0418(2) 0.4926(2) 0.1211(12) Uani 1 1 d . . . . .
H19A H 0.706112 1.060987 0.421164 0.182 Uiso 1 1 calc R U . . .
H19B H 0.837484 1.043881 0.490468 0.182 Uiso 1 1 calc R U . . .
H19C H 0.726444 1.100260 0.553007 0.182 Uiso 1 1 calc R U . . .
C20 C 0.94017(17) 0.76127(17) 0.66224(15) 0.0559(4) Uani 1 1 d . . . . .
C21 C 1.0620(2) 0.8062(2) 0.7497(2) 0.0798(6) Uani 1 1 d . . . . .
H21A H 1.073541 0.889536 0.776886 0.120 Uiso 1 1 calc R U . . .
H21B H 1.150980 0.800472 0.716878 0.120 Uiso 1 1 calc R U . . .
H21C H 1.040751 0.757920 0.812072 0.120 Uiso 1 1 calc R U . . .
C22 C 0.73076(18) 0.44714(14) 0.58995(14) 0.0499(4) Uani 1 1 d . . . . .
C23 C 0.8438(3) 0.3876(2) 0.6128(2) 0.0896(7) Uani 1 1 d . . . . .
H23A H 0.927857 0.446361 0.652388 0.134 Uiso 1 1 calc R U . . .
H23B H 0.872144 0.354971 0.541916 0.134 Uiso 1 1 calc R U . . .
H23C H 0.804066 0.323028 0.658886 0.134 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 H1 0.8200 . ?
O1 C1 1.4188(16) . ?
O2 C2 1.4433(16) . ?
O2 C14 1.3609(19) . ?
O3 C14 1.197(2) . ?
O4 C3 1.4393(16) . ?
O4 C16 1.3566(18) . ?
O5 C16 1.192(2) . ?
O6 C4 1.4404(16) . ?
O6 C18 1.341(2) . ?
O7 C18 1.188(2) . ?
O8 C5 1.4403(16) . ?
O8 C20 1.3270(19) . ?
O9 C20 1.186(2) . ?
O10 C6 1.4410(16) . ?
O10 C22 1.3441(18) . ?
O11 C22 1.196(2) . ?
N1 C9 1.3300(19) . ?
N1 C13 1.338(2) . ?
C1 C2 1.5436(19) . ?
C1 C6 1.5368(18) . ?
C1 C7 1.5331(18) . ?
C2 H2 0.9800 . ?
C2 C3 1.5233(18) . ?
C3 H3 0.9800 . ?
C3 C4 1.5180(19) . ?
C4 H4 0.9800 . ?
C4 C5 1.514(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.5294(19) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.522(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.509(2) . ?
C9 C10 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.492(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.489(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.488(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.479(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.490(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C14 O2 C2 117.39(12) . . ?
C16 O4 C3 116.56(11) . . ?
C18 O6 C4 116.78(12) . . ?
C20 O8 C5 118.62(12) . . ?
C22 O10 C6 118.05(11) . . ?
C9 N1 C13 118.09(14) . . ?
O1 C1 C2 109.94(11) . . ?
O1 C1 C6 106.10(10) . . ?
O1 C1 C7 109.27(11) . . ?
C6 C1 C2 108.11(10) . . ?
C7 C1 C2 111.46(11) . . ?
C7 C1 C6 111.82(11) . . ?
O2 C2 C1 108.48(11) . . ?
O2 C2 H2 109.9 . . ?
O2 C2 C3 108.04(11) . . ?
C1 C2 H2 109.9 . . ?
C3 C2 C1 110.51(11) . . ?
C3 C2 H2 109.9 . . ?
O4 C3 C2 109.28(11) . . ?
O4 C3 H3 110.4 . . ?
O4 C3 C4 109.01(11) . . ?
C2 C3 H3 110.4 . . ?
C4 C3 C2 107.28(11) . . ?
C4 C3 H3 110.4 . . ?
O6 C4 C3 108.61(11) . . ?
O6 C4 H4 109.3 . . ?
O6 C4 C5 109.45(11) . . ?
C3 C4 H4 109.3 . . ?
C5 C4 C3 111.00(11) . . ?
C5 C4 H4 109.3 . . ?
O8 C5 C4 108.03(11) . . ?
O8 C5 H5 109.6 . . ?
O8 C5 C6 109.81(11) . . ?
C4 C5 H5 109.6 . . ?
C4 C5 C6 110.32(11) . . ?
C6 C5 H5 109.6 . . ?
O10 C6 C1 106.20(10) . . ?
O10 C6 C5 109.54(11) . . ?
O10 C6 H6 108.8 . . ?
C1 C6 H6 108.8 . . ?
C5 C6 C1 114.70(11) . . ?
C5 C6 H6 108.8 . . ?
C1 C7 H7A 108.1 . . ?
C1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 C1 116.95(11) . . ?
C8 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.77(12) . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N1 C9 C8 118.29(13) . . ?
N1 C9 C10 121.11(14) . . ?
C10 C9 C8 120.59(14) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.60(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.17(17) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 117.94(17) . . ?
C13 C12 H12 121.0 . . ?
N1 C13 C12 124.06(16) . . ?
N1 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
O2 C14 C15 111.16(16) . . ?
O3 C14 O2 122.95(15) . . ?
O3 C14 C15 125.87(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C17 111.33(14) . . ?
O5 C16 O4 123.45(15) . . ?
O5 C16 C17 125.22(15) . . ?
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 . . ?
O6 C18 C19 110.93(18) . . ?
O7 C18 O6 123.33(17) . . ?
O7 C18 C19 125.71(19) . . ?
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 . . ?
O8 C20 C21 110.79(16) . . ?
O9 C20 O8 123.20(17) . . ?
O9 C20 C21 126.01(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O10 C22 C23 110.32(15) . . ?
O11 C22 O10 123.50(15) . . ?
O11 C22 C23 126.17(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 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 C1 C2 O2 -61.01(13) . . . . ?
O1 C1 C2 C3 57.26(14) . . . . ?
O1 C1 C6 O10 54.52(13) . . . . ?
O1 C1 C6 C5 -66.60(14) . . . . ?
O1 C1 C7 C8 -170.12(12) . . . . ?
O2 C2 C3 O4 -58.59(13) . . . . ?
O2 C2 C3 C4 -176.65(10) . . . . ?
O4 C3 C4 O6 58.06(14) . . . . ?
O4 C3 C4 C5 178.43(10) . . . . ?
O6 C4 C5 O8 55.83(14) . . . . ?
O6 C4 C5 C6 175.88(10) . . . . ?
O8 C5 C6 O10 -51.09(14) . . . . ?
O8 C5 C6 C1 68.18(14) . . . . ?
N1 C9 C10 C11 2.1(3) . . . . ?
C1 C2 C3 O4 -177.13(10) . . . . ?
C1 C2 C3 C4 64.82(13) . . . . ?
C1 C7 C8 C9 -159.94(13) . . . . ?
C2 O2 C14 O3 -1.3(2) . . . . ?
C2 O2 C14 C15 177.33(14) . . . . ?
C2 C1 C6 O10 172.42(10) . . . . ?
C2 C1 C6 C5 51.29(14) . . . . ?
C2 C1 C7 C8 68.17(16) . . . . ?
C2 C3 C4 O6 176.29(11) . . . . ?
C2 C3 C4 C5 -63.34(14) . . . . ?
C3 O4 C16 O5 -1.8(2) . . . . ?
C3 O4 C16 C17 178.03(14) . . . . ?
C3 C4 C5 O8 -64.04(13) . . . . ?
C3 C4 C5 C6 56.01(14) . . . . ?
C4 O6 C18 O7 -0.5(3) . . . . ?
C4 O6 C18 C19 -178.6(2) . . . . ?
C4 C5 C6 O10 -170.06(10) . . . . ?
C4 C5 C6 C1 -50.78(15) . . . . ?
C5 O8 C20 O9 7.9(3) . . . . ?
C5 O8 C20 C21 -171.24(15) . . . . ?
C6 O10 C22 O11 -2.6(2) . . . . ?
C6 O10 C22 C23 176.20(16) . . . . ?
C6 C1 C2 O2 -176.41(10) . . . . ?
C6 C1 C2 C3 -58.14(14) . . . . ?
C6 C1 C7 C8 -52.97(17) . . . . ?
C7 C1 C2 O2 60.31(13) . . . . ?
C7 C1 C2 C3 178.58(11) . . . . ?
C7 C1 C6 O10 -64.53(14) . . . . ?
C7 C1 C6 C5 174.35(11) . . . . ?
C7 C8 C9 N1 -3.3(2) . . . . ?
C7 C8 C9 C10 176.16(15) . . . . ?
C8 C9 C10 C11 -177.33(18) . . . . ?
C9 N1 C13 C12 0.7(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 N1 0.7(3) . . . . ?
C13 N1 C9 C8 177.37(16) . . . . ?
C13 N1 C9 C10 -2.1(2) . . . . ?
C14 O2 C2 C1 -109.30(14) . . . . ?
C14 O2 C2 C3 130.87(13) . . . . ?
C16 O4 C3 C2 131.65(13) . . . . ?
C16 O4 C3 C4 -111.38(14) . . . . ?
C18 O6 C4 C3 -142.98(16) . . . . ?
C18 O6 C4 C5 95.70(17) . . . . ?
C20 O8 C5 C4 -131.72(14) . . . . ?
C20 O8 C5 C6 107.92(15) . . . . ?
C22 O10 C6 C1 156.42(13) . . . . ?
C22 O10 C6 C5 -79.19(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.637
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-Hexane and dichloromethane'
