# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20220224_syd-19
_database_code_depnum_ccdc_archive 'CCDC 2192139'
loop_
_audit_author_name
_audit_author_address
'Yining Sang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2022-07-23 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 N O2, H2 O'
_chemical_formula_sum            'C21 H31 N O3'
_chemical_formula_weight         345.47
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.78530(10)
_cell_length_b                   9.85870(10)
_cell_length_c                   28.5856(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1912.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22588
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6720
_cell_measurement_theta_min      4.7270
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.265
_diffrn_reflns_theta_min         3.092
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  77.00   0.50    0.50    --    0.00  38.00   0.00  176
  2  ω    -13.00  17.00   0.50    0.50    --    0.00 -38.00 -90.00   60
  3  ω    -15.00  75.00   0.50    0.50    --    0.00  38.00-120.00  180
  4  ω    -28.00   5.00   0.50    0.50    --    0.00 -82.00-180.00   66
  5  ω    -27.00  28.00   0.50    0.50    --    0.00 -77.00  60.00  110
  6  ω    -14.00  12.00   0.50    0.50    --    0.00  57.00  90.00   52
  7  ω    -14.00  86.00   0.50    0.50    --    0.00  38.00 150.00  200
  8  ω     25.00  68.00   0.50    0.50    --    0.00  57.00  90.00   86
  9  ω    -19.00  28.00   0.50    0.50    --    0.00 -77.00  30.00   94
 10  ω     68.00  98.00   0.50    1.50    --   94.60  69.00 -85.93   60
 11  ω     66.00  92.00   0.50    1.50    --   94.60  74.00 113.61   52
 12  ω     66.00 102.00   0.50    1.50    --   94.60  75.00  61.07   72
 13  ω     96.00 184.00   0.50    1.50    --   94.60  74.00 113.61  176
 14  ω     68.00  94.00   0.50    1.50    --   94.60  70.00-164.98   52
 15  ω     71.00 154.00   0.50    1.50    --   94.60  59.00 109.87  166
 16  ω     73.00 121.00   0.50    1.50    --   94.60  52.00-158.35   96
 17  ω     70.00 179.00   0.50    1.50    --   94.60  64.00-136.02  218
 18  ω     70.00  97.00   0.50    1.50    --   94.60  64.00 162.24   54
 19  ω     67.00 184.00   0.50    1.50    --   94.60  72.00 -48.86  234
 20  ω     67.00  92.00   0.50    1.50    --   94.60  71.00  33.69   50
 21  ω    104.00 129.00   0.50    1.50    --   94.60  64.00 162.24   50
 22  ω     66.00 183.00   0.50    1.50    --   94.60  75.00  45.10  234
 23  ω     71.00 184.00   0.50    1.50    --   94.60  65.00-126.35  226
 24  ω     66.00  91.00   0.50    1.50    --   94.60  74.00 122.32   50
 25  ω     69.00  95.00   0.50    1.50    --   94.60  66.00 -26.49   52
 26  ω    135.00 161.00   0.50    1.50    --   94.60  66.00 -26.49   52
 27  ω     71.00  96.00   0.50    1.50    --   94.60  59.00-137.65   50
 28  ω      5.00  62.00   0.50    1.50    --   94.60 -82.00  30.00  114
 29  ω     80.00 126.00   0.50    1.50    --   94.60 -82.00  30.00   92
 30  ω     67.00  92.00   0.50    1.50    --   94.60  71.00-176.19   50
 31  ω    122.00 173.00   0.50    1.50    --   94.60  67.00 170.43  102
 32  ω     69.00  94.00   0.50    1.50    --   94.60  67.00 170.43   50
 33  ω    159.00 184.00   0.50    1.50    --   94.60  68.00 -19.29   50
 34  ω      6.00 125.00   0.50    1.50    --   94.60 -82.00 150.00  238
 35  ω     67.00  92.00   0.50    1.50    --   94.60  73.00 -65.08   50
 36  ω     71.00  98.00   0.50    1.50    --   94.60  61.00   0.00   54
 37  ω    159.00 184.00   0.50    1.50    --   94.60  61.00   0.00   50
 38  ω     46.00  72.00   0.50    1.50    --   94.60 -82.00-180.00   52
 39  ω     94.00 120.00   0.50    1.50    --   94.60 -82.00-180.00   52
 40  ω     73.00 107.00   0.50    1.50    --   94.60  58.00 -62.37   68
 41  ω    110.00 135.00   0.50    1.50    --   94.60  58.00 -62.37   50
 42  ω    140.00 171.00   0.50    1.50    --   94.60  58.00 -62.37   62
 43  ω     71.00  96.00   0.50    1.50    --   94.60  61.00 -90.00   50
 44  ω    105.00 130.00   0.50    1.50    --   94.60  61.00 -90.00   50
 45  ω     71.00  96.00   0.50    1.50    --   94.60  61.00  90.00   50
 46  ω    108.00 133.00   0.50    1.50    --   94.60  61.00  90.00   50
 47  ω     65.00 126.00   0.50    1.50    --   94.60 -82.00 -60.00  122
 48  ω     89.00 126.00   0.50    1.50    --   94.60 -82.00 -30.00   74
 49  ω     71.00 121.00   0.50    1.50    --   94.60  61.00 150.00  100
 50  ω     17.00  79.00   0.50    1.50    --   94.60 -82.00 -30.00  124
 51  ω    153.00 183.00   0.50    1.50    --   94.60  70.00-164.98   60
 52  ω     69.00 154.00   0.50    1.50    --   94.60  68.00 -19.29  170
 53  ω    156.00 182.00   0.50    1.50    --   94.60  52.00-158.35   52
 54  ω     71.00 181.00   0.50    1.50    --   94.60  61.00  30.00  220
 55  ω     71.00  96.00   0.50    1.50    --   94.60  61.00 120.00   50
 56  ω      7.00  32.00   0.50    1.50    --   94.60 -82.00-120.00   50
 57  ω     48.00  99.00   0.50    1.50    --   94.60 -82.00-120.00  102
 58  ω     71.00  96.00   0.50    1.50    --   94.60  59.00 -96.76   50
 59  ω     75.00 101.00   0.50    1.50    --   94.60  45.00 -90.00   52
 60  ω     69.00 115.00   0.50    1.50    --   94.60  68.00   6.07   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO MM007HF Cu'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262640000
_diffrn_orient_matrix_UB_12      0.0721878000
_diffrn_orient_matrix_UB_13      0.0473878000
_diffrn_orient_matrix_UB_21      -0.0583199000
_diffrn_orient_matrix_UB_22      -0.1358536000
_diffrn_orient_matrix_UB_23      0.0227666000
_diffrn_orient_matrix_UB_31      0.2178272000
_diffrn_orient_matrix_UB_32      -0.0276442000
_diffrn_orient_matrix_UB_33      0.0118100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3760
_reflns_number_total             3866
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.4589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Rigid bond restraints
 N004, C007
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 N004, C00C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
3.a Free rotating group:
 O002(H00Z,H)
3.b Ternary CH refined with riding coordinates:
 C00C(H00C)
3.c Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00F(H00D,H00F), C00I(H00G,H00H), C00N(H00T,H00U), C00O(H00V,
 H00W)
3.d Aromatic/amide H refined with riding coordinates:
 N004(H004), C009(H009), C00E(H00E)
3.e Idealised Me refined as rotating group:
 C00J(H00I,H00J,H00K), C00L(H00N,H00O,H00P), C00M(H00Q,H00R,H00S), C00P(H00X,
 H00Y,HA)
3.f Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.87994(19) 0.75514(12) 0.60041(4) 0.0201(3) Uani 1 1 d . . . . .
H001 H 0.921410 0.694499 0.583421 0.030 Uiso 1 1 calc R U . . .
O002 O 1.35821(19) 0.55874(13) 0.47561(4) 0.0230(3) Uani 1 1 d G . . . .
H00Z H 1.255764 0.581676 0.490760 0.035 Uiso 1 1 d G U . . .
H H 1.358941 0.610853 0.451908 0.035 Uiso 1 1 d G U . . .
O003 O 1.02901(19) 0.60460(14) 0.52711(4) 0.0249(3) Uani 1 1 d . . . . .
N004 N 0.7074(2) 0.54710(14) 0.52913(5) 0.0185(3) Uani 1 1 d . U . . .
H004 H 0.595218 0.550561 0.515184 0.022 Uiso 1 1 calc R U . . .
C005 C 0.7037(3) 0.71527(18) 0.62029(6) 0.0175(3) Uani 1 1 d . . . . .
C006 C 0.6148(3) 0.58984(17) 0.61079(5) 0.0171(3) Uani 1 1 d . . . . .
C007 C 0.8668(3) 0.59027(18) 0.50664(6) 0.0201(4) Uani 1 1 d . U . . .
C008 C 0.4351(3) 0.55981(17) 0.63251(6) 0.0178(3) Uani 1 1 d . . . . .
C009 C 0.6150(3) 0.80809(18) 0.64956(6) 0.0191(3) Uani 1 1 d . . . . .
H009 H 0.676017 0.891078 0.654996 0.023 Uiso 1 1 calc R U . . .
C00A C 0.4345(3) 0.77963(18) 0.67128(6) 0.0189(4) Uani 1 1 d . . . . .
C00B C 0.3461(3) 0.65309(18) 0.66373(5) 0.0179(3) Uani 1 1 d . . . . .
C00C C 0.7165(3) 0.49365(17) 0.57703(6) 0.0179(3) Uani 1 1 d . U . . .
H00C H 0.856001 0.491814 0.585856 0.021 Uiso 1 1 calc R U . . .
C00D C 0.1578(3) 0.61219(19) 0.68861(6) 0.0217(4) Uani 1 1 d . . . . .
H00A H 0.169721 0.519003 0.699118 0.026 Uiso 1 1 calc R U . . .
H00B H 0.048882 0.616614 0.666683 0.026 Uiso 1 1 calc R U . . .
C00E C 0.7261(3) 0.28726(19) 0.62481(6) 0.0226(4) Uani 1 1 d . . . . .
H00E H 0.694793 0.332543 0.652364 0.027 Uiso 1 1 calc R U . . .
C00F C 0.3342(3) 0.42511(17) 0.62343(6) 0.0207(4) Uani 1 1 d . . . . .
H00D H 0.194743 0.441275 0.618501 0.025 Uiso 1 1 calc R U . . .
H00F H 0.347515 0.368634 0.651033 0.025 Uiso 1 1 calc R U . . .
C00G C 0.3431(3) 0.88861(19) 0.70289(6) 0.0238(4) Uani 1 1 d . . . . .
C00H C 0.6413(3) 0.34542(18) 0.57990(6) 0.0202(4) Uani 1 1 d . . . . .
C00I C 0.4157(3) 0.34811(19) 0.58142(6) 0.0216(4) Uani 1 1 d . . . . .
H00G H 0.366915 0.389964 0.552974 0.026 Uiso 1 1 calc R U . . .
H00H H 0.367031 0.255624 0.582276 0.026 Uiso 1 1 calc R U . . .
C00J C 0.7110(3) 0.26532(19) 0.53728(6) 0.0256(4) Uani 1 1 d . . . . .
H00I H 0.648416 0.300235 0.509679 0.038 Uiso 1 1 calc R U . . .
H00J H 0.677081 0.171440 0.541114 0.038 Uiso 1 1 calc R U . . .
H00K H 0.851361 0.273927 0.534268 0.038 Uiso 1 1 calc R U . . .
C00K C 0.8396(3) 0.1793(2) 0.62881(7) 0.0308(4) Uani 1 1 d . . . . .
C00L C 0.8468(3) 0.6229(2) 0.45543(6) 0.0246(4) Uani 1 1 d . . . . .
H00N H 0.875789 0.717082 0.450420 0.037 Uiso 1 1 calc R U . . .
H00O H 0.714503 0.604154 0.445416 0.037 Uiso 1 1 calc R U . . .
H00P H 0.937268 0.568239 0.437791 0.037 Uiso 1 1 calc R U . . .
C00M C 0.3347(3) 1.0259(2) 0.67718(7) 0.0308(4) Uani 1 1 d . . . . .
H00Q H 0.465957 1.054599 0.669521 0.046 Uiso 1 1 calc R U . . .
H00R H 0.273700 1.092284 0.697017 0.046 Uiso 1 1 calc R U . . .
H00S H 0.259117 1.016218 0.648982 0.046 Uiso 1 1 calc R U . . .
C00N C 0.1122(3) 0.7025(2) 0.73050(7) 0.0312(5) Uani 1 1 d . . . . .
H00T H -0.020528 0.684790 0.741503 0.037 Uiso 1 1 calc R U . . .
H00U H 0.203135 0.682588 0.755775 0.037 Uiso 1 1 calc R U . . .
C00O C 0.1313(3) 0.8506(2) 0.71641(7) 0.0307(4) Uani 1 1 d . . . . .
H00V H 0.089015 0.907415 0.742238 0.037 Uiso 1 1 calc R U . . .
H00W H 0.044727 0.868404 0.690108 0.037 Uiso 1 1 calc R U . . .
C00P C 0.4716(4) 0.9045(3) 0.74663(7) 0.0360(5) Uani 1 1 d . . . . .
H00X H 0.474692 0.820242 0.763466 0.054 Uiso 1 1 calc R U . . .
H00Y H 0.417497 0.974089 0.766293 0.054 Uiso 1 1 calc R U . . .
HA H 0.603032 0.929026 0.737544 0.054 Uiso 1 1 calc R U . . .
H00L H 0.885(5) 0.119(3) 0.6015(10) 0.052(8) Uiso 1 1 d . . . . .
H00M H 0.894(4) 0.150(3) 0.6610(8) 0.035(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8200 . ?
O001 C005 1.381(2) . ?
O002 H00Z 0.8496 . ?
O002 H 0.8503 . ?
O003 C007 1.255(2) . ?
N004 H004 0.8600 . ?
N004 C007 1.328(2) . ?
N004 C00C 1.469(2) . ?
C005 C006 1.403(2) . ?
C005 C009 1.378(2) . ?
C006 C008 1.400(2) . ?
C006 C00C 1.519(2) . ?
C007 C00L 1.505(2) . ?
C008 C00B 1.417(2) . ?
C008 C00F 1.516(2) . ?
C009 H009 0.9300 . ?
C009 C00A 1.402(3) . ?
C00A C00B 1.401(2) . ?
C00A C00G 1.535(2) . ?
C00B C00D 1.517(2) . ?
C00C H00C 0.9800 . ?
C00C C00H 1.550(2) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
C00D C00N 1.524(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.519(2) . ?
C00E C00K 1.319(3) . ?
C00F H00D 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00I 1.524(2) . ?
C00G C00M 1.541(3) . ?
C00G C00O 1.535(3) . ?
C00G C00P 1.532(3) . ?
C00H C00I 1.532(3) . ?
C00H C00J 1.527(2) . ?
C00I H00G 0.9700 . ?
C00I H00H 0.9700 . ?
C00J H00I 0.9600 . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00K H00L 1.03(3) . ?
C00K H00M 1.03(2) . ?
C00L H00N 0.9600 . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00M H00Q 0.9600 . ?
C00M H00R 0.9600 . ?
C00M H00S 0.9600 . ?
C00N H00T 0.9700 . ?
C00N H00U 0.9700 . ?
C00N C00O 1.520(3) . ?
C00O H00V 0.9700 . ?
C00O H00W 0.9700 . ?
C00P H00X 0.9600 . ?
C00P H00Y 0.9600 . ?
C00P HA 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
C005 O001 H001 109.5 . . ?
H00Z O002 H 104.5 . . ?
C007 N004 H004 118.9 . . ?
C007 N004 C00C 122.16(15) . . ?
C00C N004 H004 118.9 . . ?
O001 C005 C006 122.95(15) . . ?
C009 C005 O001 116.04(16) . . ?
C009 C005 C006 120.99(16) . . ?
C005 C006 C00C 118.56(15) . . ?
C008 C006 C005 118.38(16) . . ?
C008 C006 C00C 123.06(16) . . ?
O003 C007 N004 121.65(15) . . ?
O003 C007 C00L 120.58(16) . . ?
N004 C007 C00L 117.77(16) . . ?
C006 C008 C00B 120.90(16) . . ?
C006 C008 C00F 120.15(15) . . ?
C00B C008 C00F 118.93(15) . . ?
C005 C009 H009 119.4 . . ?
C005 C009 C00A 121.18(16) . . ?
C00A C009 H009 119.4 . . ?
C009 C00A C00G 118.27(16) . . ?
C00B C00A C009 118.97(16) . . ?
C00B C00A C00G 122.76(16) . . ?
C008 C00B C00D 118.82(16) . . ?
C00A C00B C008 119.49(16) . . ?
C00A C00B C00D 121.69(15) . . ?
N004 C00C C006 110.45(14) . . ?
N004 C00C H00C 106.7 . . ?
N004 C00C C00H 111.95(14) . . ?
C006 C00C H00C 106.7 . . ?
C006 C00C C00H 113.93(14) . . ?
C00H C00C H00C 106.7 . . ?
C00B C00D H00A 109.1 . . ?
C00B C00D H00B 109.1 . . ?
C00B C00D C00N 112.58(16) . . ?
H00A C00D H00B 107.8 . . ?
C00N C00D H00A 109.1 . . ?
C00N C00D H00B 109.1 . . ?
C00H C00E H00E 116.6 . . ?
C00K C00E H00E 116.6 . . ?
C00K C00E C00H 126.81(17) . . ?
C008 C00F H00D 108.7 . . ?
C008 C00F H00F 108.7 . . ?
C008 C00F C00I 114.04(15) . . ?
H00D C00F H00F 107.6 . . ?
C00I C00F H00D 108.7 . . ?
C00I C00F H00F 108.7 . . ?
C00A C00G C00M 110.43(15) . . ?
C00A C00G C00O 110.84(16) . . ?
C00O C00G C00M 107.43(16) . . ?
C00P C00G C00A 108.79(16) . . ?
C00P C00G C00M 108.71(17) . . ?
C00P C00G C00O 110.61(16) . . ?
C00E C00H C00C 106.01(14) . . ?
C00E C00H C00I 111.19(15) . . ?
C00E C00H C00J 111.19(15) . . ?
C00I C00H C00C 108.31(15) . . ?
C00J C00H C00C 110.09(14) . . ?
C00J C00H C00I 109.95(15) . . ?
C00F C00I C00H 113.16(15) . . ?
C00F C00I H00G 108.9 . . ?
C00F C00I H00H 108.9 . . ?
C00H C00I H00G 108.9 . . ?
C00H C00I H00H 108.9 . . ?
H00G C00I H00H 107.8 . . ?
C00H C00J H00I 109.5 . . ?
C00H C00J H00J 109.5 . . ?
C00H C00J H00K 109.5 . . ?
H00I C00J H00J 109.5 . . ?
H00I C00J H00K 109.5 . . ?
H00J C00J H00K 109.5 . . ?
C00E C00K H00L 125.1(16) . . ?
C00E C00K H00M 120.7(14) . . ?
H00L C00K H00M 114(2) . . ?
C007 C00L H00N 109.5 . . ?
C007 C00L H00O 109.5 . . ?
C007 C00L H00P 109.5 . . ?
H00N C00L H00O 109.5 . . ?
H00N C00L H00P 109.5 . . ?
H00O C00L H00P 109.5 . . ?
C00G C00M H00Q 109.5 . . ?
C00G C00M H00R 109.5 . . ?
C00G C00M H00S 109.5 . . ?
H00Q C00M H00R 109.5 . . ?
H00Q C00M H00S 109.5 . . ?
H00R C00M H00S 109.5 . . ?
C00D C00N H00T 109.7 . . ?
C00D C00N H00U 109.7 . . ?
H00T C00N H00U 108.2 . . ?
C00O C00N C00D 109.61(16) . . ?
C00O C00N H00T 109.7 . . ?
C00O C00N H00U 109.7 . . ?
C00G C00O H00V 109.1 . . ?
C00G C00O H00W 109.1 . . ?
C00N C00O C00G 112.38(18) . . ?
C00N C00O H00V 109.1 . . ?
C00N C00O H00W 109.1 . . ?
H00V C00O H00W 107.9 . . ?
C00G C00P H00X 109.5 . . ?
C00G C00P H00Y 109.5 . . ?
C00G C00P HA 109.5 . . ?
H00X C00P H00Y 109.5 . . ?
H00X C00P HA 109.5 . . ?
H00Y C00P HA 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
O001 C005 C006 C008 -179.47(15) . . . . ?
O001 C005 C006 C00C -0.2(2) . . . . ?
O001 C005 C009 C00A 179.20(14) . . . . ?
N004 C00C C00H C00E 159.68(14) . . . . ?
N004 C00C C00H C00I -80.91(17) . . . . ?
N004 C00C C00H C00J 39.3(2) . . . . ?
C005 C006 C008 C00B -0.7(2) . . . . ?
C005 C006 C008 C00F -179.70(15) . . . . ?
C005 C006 C00C N004 -69.75(19) . . . . ?
C005 C006 C00C C00H 163.24(14) . . . . ?
C005 C009 C00A C00B 1.5(2) . . . . ?
C005 C009 C00A C00G -179.17(15) . . . . ?
C006 C005 C009 C00A 0.9(2) . . . . ?
C006 C008 C00B C00A 3.0(2) . . . . ?
C006 C008 C00B C00D -176.32(15) . . . . ?
C006 C008 C00F C00I -14.5(2) . . . . ?
C006 C00C C00H C00E -74.09(18) . . . . ?
C006 C00C C00H C00I 45.32(19) . . . . ?
C006 C00C C00H C00J 165.55(15) . . . . ?
C007 N004 C00C C006 111.55(18) . . . . ?
C007 N004 C00C C00H -120.35(18) . . . . ?
C008 C006 C00C N004 109.53(17) . . . . ?
C008 C006 C00C C00H -17.5(2) . . . . ?
C008 C00B C00D C00N 163.50(16) . . . . ?
C008 C00F C00I C00H 45.2(2) . . . . ?
C009 C005 C006 C008 -1.2(2) . . . . ?
C009 C005 C006 C00C 178.06(15) . . . . ?
C009 C00A C00B C008 -3.3(2) . . . . ?
C009 C00A C00B C00D 175.94(15) . . . . ?
C009 C00A C00G C00M 51.0(2) . . . . ?
C009 C00A C00G C00O 169.89(15) . . . . ?
C009 C00A C00G C00P -68.3(2) . . . . ?
C00A C00B C00D C00N -15.8(2) . . . . ?
C00A C00G C00O C00N 44.4(2) . . . . ?
C00B C008 C00F C00I 166.45(15) . . . . ?
C00B C00A C00G C00M -129.72(18) . . . . ?
C00B C00A C00G C00O -10.8(2) . . . . ?
C00B C00A C00G C00P 111.0(2) . . . . ?
C00B C00D C00N C00O 48.2(2) . . . . ?
C00C N004 C007 O003 -9.6(3) . . . . ?
C00C N004 C007 C00L 170.83(15) . . . . ?
C00C C006 C008 C00B -179.95(15) . . . . ?
C00C C006 C008 C00F 1.0(2) . . . . ?
C00C C00H C00I C00F -60.33(19) . . . . ?
C00D C00N C00O C00G -64.6(2) . . . . ?
C00E C00H C00I C00F 55.8(2) . . . . ?
C00F C008 C00B C00A -177.98(15) . . . . ?
C00F C008 C00B C00D 2.7(2) . . . . ?
C00G C00A C00B C008 177.35(15) . . . . ?
C00G C00A C00B C00D -3.4(3) . . . . ?
C00J C00H C00I C00F 179.34(15) . . . . ?
C00K C00E C00H C00C -122.0(2) . . . . ?
C00K C00E C00H C00I 120.5(2) . . . . ?
C00K C00E C00H C00J -2.4(3) . . . . ?
C00M C00G C00O C00N 165.12(16) . . . . ?
C00P C00G C00O C00N -76.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.708
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_20220513_syd-18-2
_database_code_depnum_ccdc_archive 'CCDC 2192172'
loop_
_audit_author_name
_audit_author_address
'Yining sang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2022-07-23 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.42770(10)
_cell_length_b                   10.91190(10)
_cell_length_c                   20.6052(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1670.06(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14372
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6960
_cell_measurement_theta_min      4.0410
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.911
_diffrn_reflns_theta_min         4.291
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  30.00   0.50    0.50    --    0.00 -82.00  60.00  126
  2  ω     59.00  86.00   0.50    0.50    --    0.00  38.00  60.00   54
  3  ω    -30.00   7.00   0.50    0.50    --    0.00 -82.00 120.00   74
  4  ω      2.00  28.00   0.50    0.50    --    0.00 -82.00-150.00   52
  5  ω    -33.00  28.00   0.50    0.50    --    0.00 -82.00 -60.00  122
  6  ω    -13.00  53.00   0.50    0.50    --    0.00  38.00  60.00  132
  7  ω     81.00 184.00   0.50    0.50    --   95.20  30.00-150.00  206
  8  ω     31.00  91.00   0.50    0.50    --   95.20 -82.00-120.00  120
  9  ω     81.00 156.00   0.50    0.50    --   95.20  30.00 150.00  150
 10  ω     12.00  47.00   0.50    0.50    --   95.20 -45.00 -90.00   70
 11  ω     81.00 115.00   0.50    0.50    --   95.20 -45.00 -90.00   68
 12  ω    114.00 183.00   0.50    0.50    --   95.20  30.00  90.00  138
 13  ω     12.00  38.00   0.50    0.50    --   95.20 -61.00 120.00   52
 14  ω     73.00 173.00   0.50    0.50    --   95.20  61.00   0.00  200
 15  ω     69.00 118.00   0.50    0.50    --   95.20 -82.00 -90.00   98
 16  ω     99.00 185.00   0.50    0.50    --   95.20  77.00 -30.00  172
 17  ω     11.00  80.00   0.50    0.50    --   95.20 -30.00 -60.00  138
 18  ω     82.00 115.00   0.50    0.50    --   95.20  61.00 -30.00   66
 19  ω     45.00  84.00   0.50    0.50    --   95.20 -82.00  60.00   78
 20  ω      6.00  70.00   0.50    0.50    --   95.20 -45.00  30.00  128
 21  ω     67.00 103.00   0.50    0.50    --   95.20 -61.00 120.00   72
 22  ω     96.00 124.00   0.50    0.50    --   95.20  82.00-180.00   56
 23  ω      9.00 107.00   0.50    0.50    --   95.20 -61.00-120.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0949825000
_diffrn_orient_matrix_UB_12      -0.1232742000
_diffrn_orient_matrix_UB_13      0.0125770000
_diffrn_orient_matrix_UB_21      -0.0317339000
_diffrn_orient_matrix_UB_22      0.0372776000
_diffrn_orient_matrix_UB_23      0.0711833000
_diffrn_orient_matrix_UB_31      -0.1816021000
_diffrn_orient_matrix_UB_32      0.0580037000
_diffrn_orient_matrix_UB_33      -0.0189945000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3297
_reflns_number_total             3334
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(7)
_refine_ls_extinction_coef       0.0052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.065
_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)+(0.0439P)²+0.4353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0826
_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:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00D(H00C,H00D), C00G(H00I,H00J), C00H(H00K,H00L), C00K(H00S,
 H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E)
2.d X=CH2 refined with riding coordinates:
 C00M(H00X,H00Y)
2.e Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00I(H00M,H00N,H00O), C00J(H00P,H00Q,H00R), C00L(H00U,
 H00V,H00W)
2.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.64696(16) 0.61137(11) 0.54443(5) 0.0184(3) Uani 1 1 d . . . . .
O002 O 0.34522(16) 0.68233(11) 0.46342(6) 0.0222(3) Uani 1 1 d . . . . .
H002 H 0.279014 0.742091 0.459885 0.033 Uiso 1 1 calc R U . . .
C003 C 0.6077(2) 0.76836(15) 0.31861(7) 0.0168(3) Uani 1 1 d . . . . .
C004 C 0.7569(2) 0.69137(15) 0.32640(8) 0.0173(3) Uani 1 1 d . . . . .
C005 C 0.7708(2) 0.61765(15) 0.38304(8) 0.0169(3) Uani 1 1 d . . . . .
C006 C 0.6308(2) 0.61403(15) 0.42825(7) 0.0156(3) Uani 1 1 d . . . . .
C007 C 0.6300(2) 0.53296(14) 0.48803(7) 0.0166(3) Uani 1 1 d . . . . .
H007 H 0.513378 0.491196 0.490297 0.020 Uiso 1 1 calc R U . . .
C008 C 0.4806(2) 0.68993(15) 0.41873(8) 0.0171(3) Uani 1 1 d . . . . .
C009 C 0.4722(2) 0.76713(15) 0.36553(8) 0.0184(3) Uani 1 1 d . . . . .
H009 H 0.374038 0.819337 0.360940 0.022 Uiso 1 1 calc R U . . .
C00A C 0.5893(2) 0.85754(15) 0.26122(8) 0.0199(4) Uani 1 1 d . . . . .
C00B C 0.9025(3) 0.68193(16) 0.27478(8) 0.0223(4) Uani 1 1 d . . . . .
H00A H 0.889485 0.604330 0.252299 0.027 Uiso 1 1 calc R U . . .
H00B H 1.019235 0.681966 0.295888 0.027 Uiso 1 1 calc R U . . .
C00C C 0.7792(2) 0.43492(15) 0.48776(8) 0.0205(4) Uani 1 1 d . . . . .
C00D C 0.9396(2) 0.54341(16) 0.39536(8) 0.0216(4) Uani 1 1 d . . . . .
H00C H 1.043901 0.593826 0.385923 0.026 Uiso 1 1 calc R U . . .
H00D H 0.941516 0.474116 0.365874 0.026 Uiso 1 1 calc R U . . .
C00E C 0.7232(3) 0.33598(16) 0.43974(9) 0.0245(4) Uani 1 1 d . . . . .
H00E H 0.638174 0.357866 0.408716 0.029 Uiso 1 1 calc R U . . .
C00F C 0.5131(2) 0.59190(17) 0.59313(9) 0.0243(4) Uani 1 1 d . . . . .
H00F H 0.395714 0.602443 0.574483 0.036 Uiso 1 1 calc R U . . .
H00G H 0.529638 0.649941 0.627635 0.036 Uiso 1 1 calc R U . . .
H00H H 0.524124 0.510237 0.610000 0.036 Uiso 1 1 calc R U . . .
C00G C 0.9537(2) 0.49624(16) 0.46495(9) 0.0226(4) Uani 1 1 d . . . . .
H00I H 0.981764 0.564156 0.493590 0.027 Uiso 1 1 calc R U . . .
H00J H 1.051649 0.437647 0.467697 0.027 Uiso 1 1 calc R U . . .
C00H C 0.8976(3) 0.78571(18) 0.22483(9) 0.0266(4) Uani 1 1 d . . . . .
H00K H 0.952279 0.858495 0.243326 0.032 Uiso 1 1 calc R U . . .
H00L H 0.967288 0.762182 0.187015 0.032 Uiso 1 1 calc R U . . .
C00I C 0.8048(3) 0.37981(18) 0.55538(9) 0.0269(4) Uani 1 1 d . . . . .
H00M H 0.838909 0.443218 0.585243 0.040 Uiso 1 1 calc R U . . .
H00N H 0.897391 0.318530 0.553877 0.040 Uiso 1 1 calc R U . . .
H00O H 0.693994 0.343104 0.569472 0.040 Uiso 1 1 calc R U . . .
C00J C 0.3937(3) 0.86639(19) 0.23715(9) 0.0286(4) Uani 1 1 d . . . . .
H00P H 0.352452 0.786607 0.224325 0.043 Uiso 1 1 calc R U . . .
H00Q H 0.387977 0.920999 0.200678 0.043 Uiso 1 1 calc R U . . .
H00R H 0.318640 0.897081 0.271411 0.043 Uiso 1 1 calc R U . . .
C00K C 0.7061(3) 0.81457(18) 0.20435(9) 0.0260(4) Uani 1 1 d . . . . .
H00S H 0.652572 0.741906 0.185315 0.031 Uiso 1 1 calc R U . . .
H00T H 0.708321 0.877971 0.171366 0.031 Uiso 1 1 calc R U . . .
C00L C 0.6453(3) 0.98663(16) 0.28358(9) 0.0272(4) Uani 1 1 d . . . . .
H00U H 0.568096 1.012770 0.318276 0.041 Uiso 1 1 calc R U . . .
H00V H 0.635045 1.042767 0.247894 0.041 Uiso 1 1 calc R U . . .
H00W H 0.767730 0.984865 0.298495 0.041 Uiso 1 1 calc R U . . .
C00M C 0.7828(3) 0.22343(19) 0.43775(12) 0.0356(5) Uani 1 1 d . . . . .
H00X H 0.867981 0.197114 0.467749 0.043 Uiso 1 1 calc R U . . .
H00Y H 0.739981 0.169595 0.406349 0.043 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
O001 C007 1.4487(18) . ?
O001 C00F 1.428(2) . ?
O002 H002 0.8200 . ?
O002 C008 1.3660(19) . ?
C003 C004 1.400(2) . ?
C003 C009 1.396(2) . ?
C003 C00A 1.537(2) . ?
C004 C005 1.421(2) . ?
C004 C00B 1.521(2) . ?
C005 C006 1.397(2) . ?
C005 C00D 1.514(2) . ?
C006 C007 1.517(2) . ?
C006 C008 1.403(2) . ?
C007 H007 0.9800 . ?
C007 C00C 1.540(2) . ?
C008 C009 1.384(2) . ?
C009 H009 0.9300 . ?
C00A C00J 1.538(2) . ?
C00A C00K 1.532(2) . ?
C00A C00L 1.539(2) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00B C00H 1.531(2) . ?
C00C C00E 1.522(2) . ?
C00C C00G 1.533(2) . ?
C00C C00I 1.529(2) . ?
C00D H00C 0.9700 . ?
C00D H00D 0.9700 . ?
C00D C00G 1.527(2) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.306(3) . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00G H00I 0.9700 . ?
C00G H00J 0.9700 . ?
C00H H00K 0.9700 . ?
C00H H00L 0.9700 . ?
C00H C00K 1.517(3) . ?
C00I H00M 0.9600 . ?
C00I H00N 0.9600 . ?
C00I H00O 0.9600 . ?
C00J H00P 0.9600 . ?
C00J H00Q 0.9600 . ?
C00J H00R 0.9600 . ?
C00K H00S 0.9700 . ?
C00K H00T 0.9700 . ?
C00L H00U 0.9600 . ?
C00L H00V 0.9600 . ?
C00L H00W 0.9600 . ?
C00M H00X 0.9300 . ?
C00M H00Y 0.9300 . ?

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
C00F O001 C007 114.53(12) . . ?
C008 O002 H002 109.5 . . ?
C004 C003 C00A 122.57(15) . . ?
C009 C003 C004 119.06(15) . . ?
C009 C003 C00A 118.35(15) . . ?
C003 C004 C005 119.45(14) . . ?
C003 C004 C00B 121.57(15) . . ?
C005 C004 C00B 118.96(14) . . ?
C004 C005 C00D 120.06(14) . . ?
C006 C005 C004 120.62(15) . . ?
C006 C005 C00D 119.31(14) . . ?
C005 C006 C007 124.13(14) . . ?
C005 C006 C008 118.82(14) . . ?
C008 C006 C007 117.05(14) . . ?
O001 C007 C006 107.86(12) . . ?
O001 C007 H007 108.3 . . ?
O001 C007 C00C 110.52(13) . . ?
C006 C007 H007 108.3 . . ?
C006 C007 C00C 113.54(13) . . ?
C00C C007 H007 108.3 . . ?
O002 C008 C006 117.09(14) . . ?
O002 C008 C009 122.52(15) . . ?
C009 C008 C006 120.39(15) . . ?
C003 C009 H009 119.3 . . ?
C008 C009 C003 121.46(15) . . ?
C008 C009 H009 119.3 . . ?
C003 C00A C00J 111.82(14) . . ?
C003 C00A C00L 108.97(13) . . ?
C00J C00A C00L 107.11(15) . . ?
C00K C00A C003 110.15(14) . . ?
C00K C00A C00J 107.91(14) . . ?
C00K C00A C00L 110.86(15) . . ?
C004 C00B H00A 108.8 . . ?
C004 C00B H00B 108.8 . . ?
C004 C00B C00H 113.79(15) . . ?
H00A C00B H00B 107.7 . . ?
C00H C00B H00A 108.8 . . ?
C00H C00B H00B 108.8 . . ?
C00E C00C C007 107.36(14) . . ?
C00E C00C C00G 109.95(14) . . ?
C00E C00C C00I 110.32(14) . . ?
C00G C00C C007 107.85(13) . . ?
C00I C00C C007 111.04(14) . . ?
C00I C00C C00G 110.25(15) . . ?
C005 C00D H00C 108.9 . . ?
C005 C00D H00D 108.9 . . ?
C005 C00D C00G 113.25(14) . . ?
H00C C00D H00D 107.7 . . ?
C00G C00D H00C 108.9 . . ?
C00G C00D H00D 108.9 . . ?
C00C C00E H00E 116.8 . . ?
C00M C00E C00C 126.50(18) . . ?
C00M C00E H00E 116.8 . . ?
O001 C00F H00F 109.5 . . ?
O001 C00F H00G 109.5 . . ?
O001 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?
C00C C00G H00I 109.2 . . ?
C00C C00G H00J 109.2 . . ?
C00D C00G C00C 112.14(15) . . ?
C00D C00G H00I 109.2 . . ?
C00D C00G H00J 109.2 . . ?
H00I C00G H00J 107.9 . . ?
C00B C00H H00K 109.4 . . ?
C00B C00H H00L 109.4 . . ?
H00K C00H H00L 108.0 . . ?
C00K C00H C00B 111.28(15) . . ?
C00K C00H H00K 109.4 . . ?
C00K C00H H00L 109.4 . . ?
C00C C00I H00M 109.5 . . ?
C00C C00I H00N 109.5 . . ?
C00C C00I H00O 109.5 . . ?
H00M C00I H00N 109.5 . . ?
H00M C00I H00O 109.5 . . ?
H00N C00I H00O 109.5 . . ?
C00A C00J H00P 109.5 . . ?
C00A C00J H00Q 109.5 . . ?
C00A C00J H00R 109.5 . . ?
H00P C00J H00Q 109.5 . . ?
H00P C00J H00R 109.5 . . ?
H00Q C00J H00R 109.5 . . ?
C00A C00K H00S 109.1 . . ?
C00A C00K H00T 109.1 . . ?
C00H C00K C00A 112.45(15) . . ?
C00H C00K H00S 109.1 . . ?
C00H C00K H00T 109.1 . . ?
H00S C00K H00T 107.8 . . ?
C00A C00L H00U 109.5 . . ?
C00A C00L H00V 109.5 . . ?
C00A C00L H00W 109.5 . . ?
H00U C00L H00V 109.5 . . ?
H00U C00L H00W 109.5 . . ?
H00V C00L H00W 109.5 . . ?
C00E C00M H00X 120.0 . . ?
C00E C00M H00Y 120.0 . . ?
H00X C00M H00Y 120.0 . . ?

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
O001 C007 C00C C00E 164.05(13) . . . . ?
O001 C007 C00C C00G -77.51(16) . . . . ?
O001 C007 C00C C00I 43.38(19) . . . . ?
O002 C008 C009 C003 -176.40(15) . . . . ?
C003 C004 C005 C006 5.1(2) . . . . ?
C003 C004 C005 C00D -173.99(15) . . . . ?
C003 C004 C00B C00H 15.5(2) . . . . ?
C003 C00A C00K C00H -49.8(2) . . . . ?
C004 C003 C009 C008 -1.2(2) . . . . ?
C004 C003 C00A C00J 142.68(16) . . . . ?
C004 C003 C00A C00K 22.7(2) . . . . ?
C004 C003 C00A C00L -99.11(18) . . . . ?
C004 C005 C006 C007 176.59(14) . . . . ?
C004 C005 C006 C008 -3.7(2) . . . . ?
C004 C005 C00D C00G 165.28(15) . . . . ?
C004 C00B C00H C00K -42.1(2) . . . . ?
C005 C004 C00B C00H -166.14(15) . . . . ?
C005 C006 C007 O001 110.94(16) . . . . ?
C005 C006 C007 C00C -11.9(2) . . . . ?
C005 C006 C008 O002 178.96(14) . . . . ?
C005 C006 C008 C009 -0.2(2) . . . . ?
C005 C00D C00G C00C 48.5(2) . . . . ?
C006 C005 C00D C00G -13.9(2) . . . . ?
C006 C007 C00C C00E -74.60(17) . . . . ?
C006 C007 C00C C00G 43.84(18) . . . . ?
C006 C007 C00C C00I 164.74(14) . . . . ?
C006 C008 C009 C003 2.7(2) . . . . ?
C007 C006 C008 O002 -1.3(2) . . . . ?
C007 C006 C008 C009 179.53(14) . . . . ?
C007 C00C C00E C00M -159.6(2) . . . . ?
C007 C00C C00G C00D -63.33(17) . . . . ?
C008 C006 C007 O001 -68.77(17) . . . . ?
C008 C006 C007 C00C 168.40(14) . . . . ?
C009 C003 C004 C005 -2.6(2) . . . . ?
C009 C003 C004 C00B 175.69(15) . . . . ?
C009 C003 C00A C00J -39.1(2) . . . . ?
C009 C003 C00A C00K -159.12(15) . . . . ?
C009 C003 C00A C00L 79.1(2) . . . . ?
C00A C003 C004 C005 175.54(15) . . . . ?
C00A C003 C004 C00B -6.1(2) . . . . ?
C00A C003 C009 C008 -179.49(15) . . . . ?
C00B C004 C005 C006 -173.22(15) . . . . ?
C00B C004 C005 C00D 7.6(2) . . . . ?
C00B C00H C00K C00A 61.3(2) . . . . ?
C00D C005 C006 C007 -4.3(2) . . . . ?
C00D C005 C006 C008 175.44(15) . . . . ?
C00E C00C C00G C00D 53.43(19) . . . . ?
C00F O001 C007 C006 127.97(14) . . . . ?
C00F O001 C007 C00C -107.37(16) . . . . ?
C00G C00C C00E C00M 83.3(2) . . . . ?
C00I C00C C00E C00M -38.5(3) . . . . ?
C00I C00C C00G C00D 175.28(14) . . . . ?
C00J C00A C00K C00H -172.10(15) . . . . ?
C00L C00A C00K C00H 70.91(19) . . . . ?

_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 2.614
_oxdiff_exptl_absorpt_empirical_full_min 0.397
####################################################################### 
# 
# 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_20220513_syd-18-1
_database_code_depnum_ccdc_archive 'CCDC 2192174'
loop_
_audit_author_name
_audit_author_address
'Yining sang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2022-07-23 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.48213(5)
_cell_length_b                   15.39450(9)
_cell_length_c                   17.15474(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1711.857(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27208
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      2.5740
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38508
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         3.858
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  28.00   0.50    0.50    --    0.00 -82.00  90.00  106
  2  ω      4.00  34.00   0.50    0.50    --   28.00  72.00  62.56   60
  3  ω     85.00 117.00   0.50    0.50    --   28.00  72.00  62.56   64
  4  ω    -15.00  58.00   0.50    0.50    --   40.00 -41.00-157.07  146
  5  ω    -48.00 -23.00   0.50    0.50    --   40.00 -41.00-157.07   50
  6  ω     23.00  52.00   0.50    0.50    --   48.00  72.00-169.75   58
  7  ω     22.00  91.00   0.50    0.50    --   48.00  70.00 -93.82  138
  8  ω     77.00 132.00   0.50    0.50    --   48.00  72.00-169.75  110
  9  ω    109.00 137.00   0.50    0.50    --   48.00  70.00 -93.82   56
 10  ω     90.00 139.00   0.50    0.50    --   52.00  72.00 118.07   98
 11  ω     26.00  55.00   0.50    0.50    --   52.00  72.00 -53.52   58
 12  ω     25.00  56.00   0.50    0.50    --   52.00  72.00 118.07   62
 13  ω     32.00  60.00   0.50    0.50    --   60.00  75.00  51.82   56
 14  ω     34.00  59.00   0.50    0.50    --   60.00  72.00-136.78   50
 15  ω     39.00  83.00   0.50    0.50    --   64.00  75.00 155.76   88
 16  ω    119.00 145.00   0.50    0.50    --   68.00  75.00-130.84   52
 17  ω     43.00  71.00   0.50    0.50    --   68.00  66.00 141.21   56
 18  ω     40.00  82.00   0.50    0.50    --   68.00  75.00-130.84   84
 19  ω     40.00  66.00   0.50    0.50    --   68.00  74.00  61.83   52
 20  ω     40.00  66.00   0.50    0.50    --   68.00  75.00 -20.08   52
 21  ω     40.00  70.00   0.50    0.50    --   68.00  75.00 -47.67   60
 22  ω    115.00 156.00   0.50    0.50    --   68.00  75.00 -47.67   82
 23  ω     44.00  70.00   0.50    0.50    --   72.00  75.00  79.72   52
 24  ω     44.00  83.00   0.50    0.50    --   72.00  75.00  -6.37   78
 25  ω    139.00 164.00   0.50    0.50    --   76.00  75.00-152.48   50
 26  ω     48.00  73.00   0.50    0.50    --   76.00  75.00-152.48   50
 27  ω     61.00  87.00   0.50    0.50    --   80.00  70.00  68.84   52
 28  ω     54.00  87.00   0.50    0.50    --   80.00  70.00 151.46   66
 29  ω     88.00 185.00   0.50    0.50    --   95.20  45.00 150.00  194
 30  ω     72.00 180.00   0.50    0.50    --   95.20  61.00 -90.00  216
 31  ω     69.00 125.00   0.50    0.50    --   95.20  73.00-144.29  112
 32  ω    107.00 184.00   0.50    0.50    --   95.20  74.00  17.54  154
 33  ω     67.00 101.00   0.50    0.50    --   95.20  74.00  17.54   68
 34  ω     19.00 124.00   0.50    0.50    --   95.20 -77.00  90.00  210
 35  ω     96.00 125.00   0.50    0.50    --   95.20 -77.00 -60.00   58
 36  ω    128.00 162.00   0.50    0.50    --   95.20  61.00-150.00   68
 37  ω     74.00 113.00   0.50    0.50    --   95.20  61.00-150.00   78
 38  ω     20.00  77.00   0.50    0.50    --   95.20 -77.00 -60.00  114
 39  ω     79.00 127.00   0.50    0.50    --   95.20 -82.00 150.00   96
 40  ω     42.00  67.00   0.50    0.50    --   95.20 -82.00 150.00   50
 41  ω    154.00 185.00   0.50    0.50    --   95.20  74.00  93.98   62
 42  ω     72.00 128.00   0.50    0.50    --   95.20  61.00-106.78  112
 43  ω    136.00 184.00   0.50    0.50    --   95.20  61.00-180.00   96
 44  ω     69.00 171.00   0.50    0.50    --   95.20  73.00  37.12  204
 45  ω     72.00  97.00   0.50    0.50    --   95.20  61.00-180.00   50
 46  ω     78.00 177.00   0.50    0.50    --   95.20  55.00 169.63  198
 47  ω     67.00 129.00   0.50    0.50    --   95.20  74.00  93.98  124
 48  ω     44.00 125.00   0.50    0.50    --   95.20 -82.00  60.00  162
 49  ω     74.00 169.00   0.50    0.50    --   95.20  61.00  90.00  190
 50  ω    119.00 159.00   0.50    0.50    --   95.20  74.00 -15.16   80
 51  ω     35.00 126.00   0.50    0.50    --   95.20 -82.00-120.00  182
 52  ω     67.00 116.00   0.50    0.50    --   95.20  74.00 -15.16   98
 53  ω     71.00 183.00   0.50    0.50    --   95.20  64.00 -68.87  224
 54  ω     72.00 184.00   0.50    0.50    --   95.20  61.00 -30.00  224
 55  ω     62.00 124.00   0.50    0.50    --   96.00 -82.00 -30.59  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0457396000
_diffrn_orient_matrix_UB_12      -0.0947120000
_diffrn_orient_matrix_UB_13      -0.0232127000
_diffrn_orient_matrix_UB_21      0.0687750000
_diffrn_orient_matrix_UB_22      -0.0306898000
_diffrn_orient_matrix_UB_23      0.0814277000
_diffrn_orient_matrix_UB_31      -0.2229215000
_diffrn_orient_matrix_UB_32      0.0100095000
_diffrn_orient_matrix_UB_33      0.0298736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3390
_reflns_number_total             3457
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_coef       0.0034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.3650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0767
_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:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00D,H00E), C00E(H00F,H00G), C00F(H00H,H00I), C00G(H00J,
 H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C004(H004), C00J(H00R)
2.d X=CH2 refined with riding coordinates:
 C00M(H00Y,H)
2.e Idealised Me refined as rotating group:
 C00H(H00L,H00M,H00N), C00I(H00O,H00P,H00Q), C00K(H00S,H00T,H00U), C00L(H00V,
 H00W,H00X)
2.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.50200(17) 0.81911(6) 0.60183(6) 0.0200(2) Uani 1 1 d . . . . .
O002 O 0.82847(19) 0.70680(7) 0.54011(7) 0.0233(3) Uani 1 1 d . . . . .
H002 H 0.886961 0.698014 0.498460 0.035 Uiso 1 1 calc R U . . .
C003 C 0.6757(2) 0.64690(10) 0.55007(9) 0.0187(3) Uani 1 1 d . . . . .
C004 C 0.6630(3) 0.57144(10) 0.50610(9) 0.0200(3) Uani 1 1 d . . . . .
H004 H 0.759877 0.561286 0.467168 0.024 Uiso 1 1 calc R U . . .
C005 C 0.5290(2) 0.66412(10) 0.60791(8) 0.0179(3) Uani 1 1 d . . . . .
C006 C 0.5074(3) 0.42692(10) 0.46974(9) 0.0211(3) Uani 1 1 d . . . . .
C007 C 0.5074(2) 0.51048(9) 0.51922(8) 0.0183(3) Uani 1 1 d . . . . .
C008 C 0.3686(2) 0.60524(10) 0.61982(9) 0.0184(3) Uani 1 1 d . . . . .
C009 C 0.3608(2) 0.52624(10) 0.57736(9) 0.0187(3) Uani 1 1 d . . . . .
C00A C 0.5518(2) 0.74780(9) 0.65355(9) 0.0184(3) Uani 1 1 d . . . . .
H00A H 0.696440 0.753600 0.669291 0.022 Uiso 1 1 calc R U . . .
C00B C 0.1900(3) 0.46205(10) 0.59550(10) 0.0218(3) Uani 1 1 d . . . . .
H00B H 0.061185 0.484067 0.574600 0.026 Uiso 1 1 calc R U . . .
H00C H 0.174894 0.457452 0.651600 0.026 Uiso 1 1 calc R U . . .
C00C C 0.4169(3) 0.75086(10) 0.72749(9) 0.0216(3) Uani 1 1 d . . . . .
C00D C 0.2997(3) 0.37947(10) 0.47766(9) 0.0228(3) Uani 1 1 d . . . . .
H00D H 0.195652 0.410633 0.448160 0.027 Uiso 1 1 calc R U . . .
H00E H 0.312134 0.321736 0.455499 0.027 Uiso 1 1 calc R U . . .
C00E C 0.2006(3) 0.71989(11) 0.70556(10) 0.0240(4) Uani 1 1 d . . . . .
H00F H 0.146660 0.756562 0.664351 0.029 Uiso 1 1 calc R U . . .
H00G H 0.110520 0.725656 0.750397 0.029 Uiso 1 1 calc R U . . .
C00F C 0.1999(3) 0.62533(11) 0.67816(9) 0.0227(3) Uani 1 1 d . . . . .
H00H H 0.216125 0.587677 0.723076 0.027 Uiso 1 1 calc R U . . .
H00I H 0.067178 0.612511 0.654674 0.027 Uiso 1 1 calc R U . . .
C00G C 0.2299(3) 0.37191(10) 0.56199(10) 0.0233(3) Uani 1 1 d . . . . .
H00J H 0.335572 0.342854 0.592389 0.028 Uiso 1 1 calc R U . . .
H00K H 0.104808 0.337492 0.564757 0.028 Uiso 1 1 calc R U . . .
C00H C 0.6525(3) 0.88633(10) 0.60073(10) 0.0256(4) Uani 1 1 d . . . . .
H00L H 0.625114 0.924911 0.558005 0.038 Uiso 1 1 calc R U . . .
H00M H 0.787198 0.861304 0.594637 0.038 Uiso 1 1 calc R U . . .
H00N H 0.646809 0.918141 0.648818 0.038 Uiso 1 1 calc R U . . .
C00I C 0.5418(3) 0.44666(11) 0.38293(10) 0.0254(4) Uani 1 1 d . . . . .
H00O H 0.440123 0.487627 0.365451 0.038 Uiso 1 1 calc R U . . .
H00P H 0.529555 0.393978 0.353347 0.038 Uiso 1 1 calc R U . . .
H00Q H 0.677054 0.470725 0.375740 0.038 Uiso 1 1 calc R U . . .
C00J C 0.4174(3) 0.84225(11) 0.76050(9) 0.0258(4) Uani 1 1 d . . . . .
H00R H 0.545428 0.864256 0.774926 0.031 Uiso 1 1 calc R U . . .
C00K C 0.5172(3) 0.69121(11) 0.78905(10) 0.0271(4) Uani 1 1 d . . . . .
H00S H 0.534980 0.634098 0.767602 0.041 Uiso 1 1 calc R U . . .
H00T H 0.429878 0.688057 0.834154 0.041 Uiso 1 1 calc R U . . .
H00U H 0.649159 0.714360 0.803683 0.041 Uiso 1 1 calc R U . . .
C00L C 0.6847(3) 0.36822(11) 0.49736(11) 0.0265(4) Uani 1 1 d . . . . .
H00V H 0.813725 0.397737 0.490113 0.040 Uiso 1 1 calc R U . . .
H00W H 0.684488 0.315391 0.467625 0.040 Uiso 1 1 calc R U . . .
H00X H 0.666580 0.354867 0.551591 0.040 Uiso 1 1 calc R U . . .
C00M C 0.2582(3) 0.89435(12) 0.77126(12) 0.0362(5) Uani 1 1 d . . . . .
H00Y H 0.126177 0.875952 0.757938 0.043 Uiso 1 1 calc R U . . .
H H 0.278082 0.949458 0.792161 0.043 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
O001 C00A 1.4479(17) . ?
O001 C00H 1.4223(19) . ?
O002 H002 0.8200 . ?
O002 C003 1.3637(19) . ?
C003 C004 1.388(2) . ?
C003 C005 1.400(2) . ?
C004 H004 0.9300 . ?
C004 C007 1.396(2) . ?
C005 C008 1.395(2) . ?
C005 C00A 1.515(2) . ?
C006 C007 1.541(2) . ?
C006 C00D 1.538(2) . ?
C006 C00I 1.536(2) . ?
C006 C00L 1.537(2) . ?
C007 C009 1.399(2) . ?
C008 C009 1.419(2) . ?
C008 C00F 1.514(2) . ?
C009 C00B 1.516(2) . ?
C00A H00A 0.9800 . ?
C00A C00C 1.541(2) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00G 1.524(2) . ?
C00C C00E 1.528(2) . ?
C00C C00J 1.516(2) . ?
C00C C00K 1.543(2) . ?
C00D H00D 0.9700 . ?
C00D H00E 0.9700 . ?
C00D C00G 1.520(2) . ?
C00E H00F 0.9700 . ?
C00E H00G 0.9700 . ?
C00E C00F 1.530(2) . ?
C00F H00H 0.9700 . ?
C00F H00I 0.9700 . ?
C00G H00J 0.9700 . ?
C00G H00K 0.9700 . ?
C00H H00L 0.9600 . ?
C00H H00M 0.9600 . ?
C00H H00N 0.9600 . ?
C00I H00O 0.9600 . ?
C00I H00P 0.9600 . ?
C00I H00Q 0.9600 . ?
C00J H00R 0.9300 . ?
C00J C00M 1.320(3) . ?
C00K H00S 0.9600 . ?
C00K H00T 0.9600 . ?
C00K H00U 0.9600 . ?
C00L H00V 0.9600 . ?
C00L H00W 0.9600 . ?
C00L H00X 0.9600 . ?
C00M H00Y 0.9300 . ?
C00M H 0.9300 . ?

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
C00H O001 C00A 114.01(12) . . ?
C003 O002 H002 109.5 . . ?
O002 C003 C004 122.77(14) . . ?
O002 C003 C005 117.00(13) . . ?
C004 C003 C005 120.23(14) . . ?
C003 C004 H004 119.4 . . ?
C003 C004 C007 121.22(14) . . ?
C007 C004 H004 119.4 . . ?
C003 C005 C00A 117.48(13) . . ?
C008 C005 C003 119.17(13) . . ?
C008 C005 C00A 123.34(14) . . ?
C00D C006 C007 110.35(13) . . ?
C00I C006 C007 111.64(12) . . ?
C00I C006 C00D 107.85(13) . . ?
C00I C006 C00L 107.87(14) . . ?
C00L C006 C007 108.72(13) . . ?
C00L C006 C00D 110.38(13) . . ?
C004 C007 C006 118.19(14) . . ?
C004 C007 C009 119.29(13) . . ?
C009 C007 C006 122.50(14) . . ?
C005 C008 C009 120.57(14) . . ?
C005 C008 C00F 120.17(14) . . ?
C009 C008 C00F 119.25(14) . . ?
C007 C009 C008 119.37(14) . . ?
C007 C009 C00B 121.96(14) . . ?
C008 C009 C00B 118.66(14) . . ?
O001 C00A C005 107.85(11) . . ?
O001 C00A H00A 108.2 . . ?
O001 C00A C00C 110.78(12) . . ?
C005 C00A H00A 108.2 . . ?
C005 C00A C00C 113.34(13) . . ?
C00C C00A H00A 108.2 . . ?
C009 C00B H00B 109.0 . . ?
C009 C00B H00C 109.0 . . ?
C009 C00B C00G 113.09(14) . . ?
H00B C00B H00C 107.8 . . ?
C00G C00B H00B 109.0 . . ?
C00G C00B H00C 109.0 . . ?
C00A C00C C00K 107.83(13) . . ?
C00E C00C C00A 107.95(12) . . ?
C00E C00C C00K 111.67(14) . . ?
C00J C00C C00A 109.55(13) . . ?
C00J C00C C00E 112.53(14) . . ?
C00J C00C C00K 107.20(13) . . ?
C006 C00D H00D 109.1 . . ?
C006 C00D H00E 109.1 . . ?
H00D C00D H00E 107.9 . . ?
C00G C00D C006 112.38(13) . . ?
C00G C00D H00D 109.1 . . ?
C00G C00D H00E 109.1 . . ?
C00C C00E H00F 109.2 . . ?
C00C C00E H00G 109.2 . . ?
C00C C00E C00F 112.07(14) . . ?
H00F C00E H00G 107.9 . . ?
C00F C00E H00F 109.2 . . ?
C00F C00E H00G 109.2 . . ?
C008 C00F C00E 113.27(13) . . ?
C008 C00F H00H 108.9 . . ?
C008 C00F H00I 108.9 . . ?
C00E C00F H00H 108.9 . . ?
C00E C00F H00I 108.9 . . ?
H00H C00F H00I 107.7 . . ?
C00B C00G H00J 109.7 . . ?
C00B C00G H00K 109.7 . . ?
C00D C00G C00B 109.86(13) . . ?
C00D C00G H00J 109.7 . . ?
C00D C00G H00K 109.7 . . ?
H00J C00G H00K 108.2 . . ?
O001 C00H H00L 109.5 . . ?
O001 C00H H00M 109.5 . . ?
O001 C00H H00N 109.5 . . ?
H00L C00H H00M 109.5 . . ?
H00L C00H H00N 109.5 . . ?
H00M C00H H00N 109.5 . . ?
C006 C00I H00O 109.5 . . ?
C006 C00I H00P 109.5 . . ?
C006 C00I H00Q 109.5 . . ?
H00O C00I H00P 109.5 . . ?
H00O C00I H00Q 109.5 . . ?
H00P C00I H00Q 109.5 . . ?
C00C C00J H00R 116.0 . . ?
C00M C00J C00C 127.91(17) . . ?
C00M C00J H00R 116.0 . . ?
C00C C00K H00S 109.5 . . ?
C00C C00K H00T 109.5 . . ?
C00C C00K H00U 109.5 . . ?
H00S C00K H00T 109.5 . . ?
H00S C00K H00U 109.5 . . ?
H00T C00K H00U 109.5 . . ?
C006 C00L H00V 109.5 . . ?
C006 C00L H00W 109.5 . . ?
C006 C00L H00X 109.5 . . ?
H00V C00L H00W 109.5 . . ?
H00V C00L H00X 109.5 . . ?
H00W C00L H00X 109.5 . . ?
C00J C00M H00Y 120.0 . . ?
C00J C00M H 120.0 . . ?
H00Y C00M H 120.0 . . ?

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
O001 C00A C00C C00E 75.15(15) . . . . ?
O001 C00A C00C C00J -47.71(17) . . . . ?
O001 C00A C00C C00K -164.06(13) . . . . ?
O002 C003 C004 C007 178.36(14) . . . . ?
O002 C003 C005 C008 179.37(13) . . . . ?
O002 C003 C005 C00A 0.6(2) . . . . ?
C003 C004 C007 C006 -178.12(14) . . . . ?
C003 C004 C007 C009 0.6(2) . . . . ?
C003 C005 C008 C009 3.9(2) . . . . ?
C003 C005 C008 C00F -175.79(14) . . . . ?
C003 C005 C00A O001 70.57(16) . . . . ?
C003 C005 C00A C00C -166.40(14) . . . . ?
C004 C003 C005 C008 -1.0(2) . . . . ?
C004 C003 C005 C00A -179.81(14) . . . . ?
C004 C007 C009 C008 2.3(2) . . . . ?
C004 C007 C009 C00B -178.96(14) . . . . ?
C005 C003 C004 C007 -1.2(2) . . . . ?
C005 C008 C009 C007 -4.6(2) . . . . ?
C005 C008 C009 C00B 176.65(14) . . . . ?
C005 C008 C00F C00E 12.8(2) . . . . ?
C005 C00A C00C C00E -46.24(17) . . . . ?
C005 C00A C00C C00J -169.10(13) . . . . ?
C005 C00A C00C C00K 74.55(16) . . . . ?
C006 C007 C009 C008 -179.08(14) . . . . ?
C006 C007 C009 C00B -0.4(2) . . . . ?
C006 C00D C00G C00B 64.10(17) . . . . ?
C007 C006 C00D C00G -46.87(18) . . . . ?
C007 C009 C00B C00G 16.2(2) . . . . ?
C008 C005 C00A O001 -108.17(16) . . . . ?
C008 C005 C00A C00C 14.9(2) . . . . ?
C008 C009 C00B C00G -165.11(14) . . . . ?
C009 C008 C00F C00E -166.93(13) . . . . ?
C009 C00B C00G C00D -46.51(18) . . . . ?
C00A C005 C008 C009 -177.37(13) . . . . ?
C00A C005 C008 C00F 2.9(2) . . . . ?
C00A C00C C00E C00F 63.32(16) . . . . ?
C00A C00C C00J C00M 119.97(19) . . . . ?
C00C C00E C00F C008 -46.63(19) . . . . ?
C00D C006 C007 C004 -166.01(14) . . . . ?
C00D C006 C007 C009 15.4(2) . . . . ?
C00E C00C C00J C00M -0.1(2) . . . . ?
C00F C008 C009 C007 175.13(14) . . . . ?
C00F C008 C009 C00B -3.6(2) . . . . ?
C00H O001 C00A C005 -129.57(14) . . . . ?
C00H O001 C00A C00C 105.85(15) . . . . ?
C00I C006 C007 C004 -46.08(19) . . . . ?
C00I C006 C007 C009 135.29(16) . . . . ?
C00I C006 C00D C00G -169.05(14) . . . . ?
C00J C00C C00E C00F -175.67(13) . . . . ?
C00K C00C C00E C00F -55.05(17) . . . . ?
C00K C00C C00J C00M -123.3(2) . . . . ?
C00L C006 C007 C004 72.80(17) . . . . ?
C00L C006 C007 C009 -105.82(17) . . . . ?
C00L C006 C00D C00G 73.33(17) . . . . ?

_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 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.407
