# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_7327
_database_code_depnum_ccdc_archive 'CCDC 1958259'
loop_
_audit_author_name
_audit_author_address
'Simon Herbert'
;HUAqiao
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H38 O5'
_chemical_formula_sum            'C29 H38 O5'
_chemical_formula_weight         466.59
_chemical_absolute_configuration rm
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   10.0470(9)
_cell_length_b                   11.0487(7)
_cell_length_c                   24.2420(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2691.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1560
_cell_measurement_theta_min      4.0490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.433
_diffrn_reflns_theta_min         3.362
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  51.00   1.00   12.50    --   15.49  19.00  60.00   64
  2  ω     56.00  87.00   1.00   12.50    --   15.49  19.00  60.00   31
  3  ω      1.00  27.00   1.00   12.50    --   15.49 -57.00 -30.00   26
  4  ω    -23.00  21.00   1.00   12.50    --  -16.12 -99.00  30.00   44
  5  ω    -54.00  33.00   1.00   12.50    --   15.49 -38.00-120.00   87
  6  ω     -2.00  54.00   1.00   12.50    --   15.49 -99.00-180.00   56
  7  ω     -1.00  29.00   1.00   12.50    --   15.49  57.00 -60.00   30
  8  ω     43.00  75.00   1.00   12.50    --   15.49 178.00-180.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0314987000
_diffrn_orient_matrix_UB_12      0.0325452000
_diffrn_orient_matrix_UB_13      0.0215813000
_diffrn_orient_matrix_UB_21      -0.0617282000
_diffrn_orient_matrix_UB_22      0.0045823000
_diffrn_orient_matrix_UB_23      0.0140514000
_diffrn_orient_matrix_UB_31      0.0134783000
_diffrn_orient_matrix_UB_32      -0.0551279000
_diffrn_orient_matrix_UB_33      0.0139049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                3790
_reflns_number_total             6455
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6455
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      4.125
_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)+(0.0807P)²+0.0384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1814
_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. Restrained distances
 H00C-H00X
 1.8 with sigma of 0.02
 H00C-H00Z
 1.8 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C00M(H00M)
3.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00C), C00U(H00Y,H), C00X(H0AA,HE)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00G(H00G), C00H(H00H), C00L(H00L), C00N(H00N)
3.d Idealised Me refined as rotating group:
 C00P(H00D,H00E,H00I), C00Q(H00J,H00K,H00O), C00R(H00P,H00Q,H00R), C00S(H00S,
 H00T,H00U), C00T(H00V,H00W,H00X), C00V(H00Z,HA,HB), C00W(H00,HC,HD), C00Y(H1AA,
 HF,HG)
3.e 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 0.7637(3) 0.6538(2) 0.24149(9) 0.0600(8) Uani 1 1 d . . . . .
O002 O 0.5818(3) 0.4748(3) 0.56794(10) 0.0721(9) Uani 1 1 d . . . . .
H002 H 0.622076 0.523129 0.587432 0.108 Uiso 1 1 calc GR . . . .
O003 O 0.9311(4) 0.6761(3) 0.34455(12) 0.0786(10) Uani 1 1 d . . . . .
O004 O 0.7962(3) 0.4609(3) 0.21835(11) 0.0677(8) Uani 1 1 d . . . . .
O005 O 0.1675(4) 0.5529(3) 0.22277(13) 0.0821(10) Uani 1 1 d . . . . .
C006 C 0.5283(4) 0.5669(3) 0.30729(13) 0.0442(9) Uani 1 1 d . . . . .
C007 C 0.5195(4) 0.4431(3) 0.47476(13) 0.0429(8) Uani 1 1 d . . . . .
C008 C 0.4071(4) 0.3574(4) 0.49272(15) 0.0522(10) Uani 1 1 d . . . . .
C009 C 0.6037(4) 0.5021(3) 0.51321(13) 0.0489(9) Uani 1 1 d . . . . .
C00A C 0.7029(4) 0.5824(3) 0.49752(13) 0.0424(8) Uani 1 1 d . . . . .
C00B C 0.5405(4) 0.4701(3) 0.41957(14) 0.0450(9) Uani 1 1 d . . . . .
H00B H 0.487377 0.432515 0.393249 0.054 Uiso 1 1 calc R . . . .
C00C C 0.9116(5) 0.5698(5) 0.33751(15) 0.0643(12) Uani 1 1 d . . . . .
C00D C 0.2878(4) 0.5519(4) 0.24986(15) 0.0547(10) Uani 1 1 d . . . . .
C00E C 0.7786(4) 0.5157(3) 0.31519(14) 0.0486(9) Uani 1 1 d . . . . .
C00F C 0.7163(4) 0.6067(3) 0.44160(14) 0.0470(9) Uani 1 1 d . . . . .
H00F H 0.780259 0.662308 0.430263 0.056 Uiso 1 1 calc R . . . .
C00G C 0.4364(5) 0.6593(3) 0.30879(14) 0.0525(10) Uani 1 1 d . . . . .
H00G H 0.455373 0.728382 0.329254 0.063 Uiso 1 1 calc R . . . .
C00H C 0.4961(4) 0.4662(4) 0.27712(15) 0.0529(10) Uani 1 1 d . . . . .
H00H H 0.555505 0.401644 0.276095 0.063 Uiso 1 1 calc R . . . .
C00I C 0.7812(4) 0.5367(4) 0.25300(15) 0.0504(9) Uani 1 1 d . . . . .
C00J C 0.7942(5) 0.6472(4) 0.53921(14) 0.0536(10) Uani 1 1 d . . . . .
C00K C 0.6374(4) 0.5508(3) 0.40195(13) 0.0447(9) Uani 1 1 d . . . . .
C00L C 0.3179(5) 0.6526(4) 0.28104(16) 0.0619(12) Uani 1 1 d . . . . .
H00L H 0.257475 0.716154 0.283243 0.074 Uiso 1 1 calc R . . . .
C00M C 0.6566(4) 0.5813(3) 0.34078(13) 0.0439(9) Uani 1 1 d . . . . .
H00M H 0.677933 0.667829 0.339599 0.053 Uiso 1 1 calc R . . . .
C00N C 0.3774(5) 0.4575(4) 0.24802(16) 0.0586(10) Uani 1 1 d . . . . .
H00N H 0.358525 0.388538 0.227453 0.070 Uiso 1 1 calc R . . . .
C00O C 0.7957(5) 0.3808(4) 0.32850(17) 0.0613(11) Uani 1 1 d . . . . .
H00A H 0.761508 0.362847 0.365010 0.074 Uiso 1 1 calc R . . . .
H00C H 0.748557 0.331462 0.301793 0.074 Uiso 1 1 calc DR . . . .
C00P C 0.3337(5) 0.3056(4) 0.44323(19) 0.0724(14) Uani 1 1 d . . . . .
H00D H 0.294199 0.370259 0.422486 0.109 Uiso 1 1 calc GR . . . .
H00E H 0.265335 0.251398 0.455715 0.109 Uiso 1 1 calc GR . . . .
H00I H 0.395261 0.262266 0.420248 0.109 Uiso 1 1 calc GR . . . .
C00Q C 0.3052(6) 0.4244(5) 0.5280(2) 0.0885(17) Uani 1 1 d . . . . .
H00J H 0.348026 0.455862 0.560350 0.133 Uiso 1 1 calc GR . . . .
H00K H 0.235755 0.369566 0.538672 0.133 Uiso 1 1 calc GR . . . .
H00O H 0.267814 0.489909 0.507095 0.133 Uiso 1 1 calc GR . . . .
C00R C 0.7465(6) 0.6831(4) 0.18419(15) 0.0743(15) Uani 1 1 d . . . . .
H00P H 0.820239 0.651879 0.163403 0.111 Uiso 1 1 calc GR . . . .
H00Q H 0.742456 0.769420 0.179921 0.111 Uiso 1 1 calc GR . . . .
H00R H 0.665341 0.647652 0.170951 0.111 Uiso 1 1 calc GR . . . .
C00S C 0.4620(6) 0.2498(5) 0.5250(2) 0.0823(16) Uani 1 1 d . . . . .
H00S H 0.524054 0.206118 0.502399 0.124 Uiso 1 1 calc GR . . . .
H00T H 0.390091 0.197166 0.535304 0.124 Uiso 1 1 calc GR . . . .
H00U H 0.506277 0.278275 0.557590 0.124 Uiso 1 1 calc GR . . . .
C00T C 0.1434(6) 0.4548(6) 0.1871(2) 0.1008(19) Uani 1 1 d . . . . .
H00V H 0.136244 0.483709 0.149879 0.151 Uiso 1 1 calc GR . . . .
H00W H 0.061851 0.415552 0.197485 0.151 Uiso 1 1 calc GR . . . .
H00X H 0.215532 0.398090 0.189620 0.151 Uiso 1 1 calc DGR . . . .
C00U C 1.0059(5) 0.4694(6) 0.3507(2) 0.0873(16) Uani 1 1 d . . . . .
H00Y H 1.015623 0.460515 0.390335 0.105 Uiso 1 1 calc R . . . .
H H 1.092737 0.485142 0.334802 0.105 Uiso 1 1 calc R . . . .
C00V C 0.8750(6) 0.5540(5) 0.5715(2) 0.0892(16) Uani 1 1 d . . . . .
H00Z H 0.899101 0.488370 0.547506 0.134 Uiso 1 1 calc DGR . . . .
HA H 0.822489 0.523494 0.601519 0.134 Uiso 1 1 calc GR . . . .
HB H 0.954072 0.591387 0.585694 0.134 Uiso 1 1 calc GR . . . .
C00W C 0.8970(7) 0.7264(6) 0.5104(2) 0.097(2) Uani 1 1 d . . . . .
H00 H 0.949466 0.677653 0.485930 0.146 Uiso 1 1 calc GR . . . .
HC H 0.953840 0.763111 0.537521 0.146 Uiso 1 1 calc GR . . . .
HD H 0.852414 0.788437 0.489754 0.146 Uiso 1 1 calc GR . . . .
C00X C 0.9448(6) 0.3565(5) 0.3258(2) 0.0807(15) Uani 1 1 d . . . . .
H0AA H 0.968227 0.285122 0.346972 0.097 Uiso 1 1 calc R . . . .
HE H 0.973854 0.345420 0.287936 0.097 Uiso 1 1 calc R . . . .
C00Y C 0.7140(7) 0.7291(6) 0.5771(2) 0.103(2) Uani 1 1 d . . . . .
H1AA H 0.656785 0.779807 0.555346 0.155 Uiso 1 1 calc GR . . . .
HF H 0.773498 0.778754 0.598263 0.155 Uiso 1 1 calc GR . . . .
HG H 0.661130 0.680571 0.601531 0.155 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00I 1.335(5) . ?
O001 C00R 1.437(4) . ?
O002 C009 1.378(4) . ?
O003 C00C 1.202(5) . ?
O004 C00I 1.196(4) . ?
O005 C00D 1.375(5) . ?
O005 C00T 1.408(6) . ?
C006 C00G 1.378(6) . ?
C006 C00H 1.370(5) . ?
C006 C00M 1.531(5) . ?
C007 C008 1.536(5) . ?
C007 C009 1.418(5) . ?
C007 C00B 1.387(4) . ?
C008 C00P 1.520(6) . ?
C008 C00Q 1.525(7) . ?
C008 C00S 1.527(6) . ?
C009 C00A 1.388(5) . ?
C00A C00F 1.389(5) . ?
C00A C00J 1.541(5) . ?
C00B C00K 1.387(5) . ?
C00C C00E 1.561(6) . ?
C00C C00U 1.493(7) . ?
C00D C00L 1.379(6) . ?
C00D C00N 1.379(6) . ?
C00E C00I 1.525(5) . ?
C00E C00M 1.553(5) . ?
C00E C00O 1.534(5) . ?
C00F C00K 1.391(5) . ?
C00G C00L 1.370(6) . ?
C00H C00N 1.389(6) . ?
C00J C00V 1.527(6) . ?
C00J C00W 1.523(7) . ?
C00J C00Y 1.520(7) . ?
C00K C00M 1.533(5) . ?
C00O C00X 1.524(7) . ?
C00U C00X 1.517(8) . ?

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
C00I O001 C00R 115.9(3) . . ?
C00D O005 C00T 116.0(4) . . ?
C00G C006 C00M 118.2(3) . . ?
C00H C006 C00G 117.2(4) . . ?
C00H C006 C00M 124.5(3) . . ?
C009 C007 C008 122.4(3) . . ?
C00B C007 C008 121.2(3) . . ?
C00B C007 C009 116.4(3) . . ?
C00P C008 C007 111.4(3) . . ?
C00P C008 C00Q 107.4(4) . . ?
C00P C008 C00S 106.6(4) . . ?
C00Q C008 C007 110.7(4) . . ?
C00Q C008 C00S 109.5(4) . . ?
C00S C008 C007 111.1(4) . . ?
O002 C009 C007 115.9(3) . . ?
O002 C009 C00A 121.2(3) . . ?
C00A C009 C007 122.8(3) . . ?
C009 C00A C00F 117.5(3) . . ?
C009 C00A C00J 123.0(3) . . ?
C00F C00A C00J 119.5(3) . . ?
C00K C00B C007 122.8(3) . . ?
O003 C00C C00E 124.2(5) . . ?
O003 C00C C00U 126.3(5) . . ?
C00U C00C C00E 109.4(4) . . ?
O005 C00D C00L 116.6(4) . . ?
O005 C00D C00N 124.4(4) . . ?
C00N C00D C00L 119.0(4) . . ?
C00I C00E C00C 105.6(3) . . ?
C00I C00E C00M 109.7(3) . . ?
C00I C00E C00O 110.7(3) . . ?
C00M C00E C00C 111.0(3) . . ?
C00O C00E C00C 101.7(4) . . ?
C00O C00E C00M 117.2(3) . . ?
C00A C00F C00K 122.2(3) . . ?
C00L C00G C006 122.0(4) . . ?
C006 C00H C00N 122.0(4) . . ?
O001 C00I C00E 110.6(3) . . ?
O004 C00I O001 123.3(3) . . ?
O004 C00I C00E 126.1(4) . . ?
C00V C00J C00A 109.8(3) . . ?
C00W C00J C00A 111.7(3) . . ?
C00W C00J C00V 105.2(5) . . ?
C00Y C00J C00A 110.9(4) . . ?
C00Y C00J C00V 112.0(4) . . ?
C00Y C00J C00W 107.1(4) . . ?
C00B C00K C00F 118.2(3) . . ?
C00B C00K C00M 121.9(3) . . ?
C00F C00K C00M 119.9(3) . . ?
C00G C00L C00D 120.3(4) . . ?
C006 C00M C00E 113.8(3) . . ?
C006 C00M C00K 112.6(3) . . ?
C00K C00M C00E 112.5(3) . . ?
C00D C00N C00H 119.5(4) . . ?
C00X C00O C00E 105.8(4) . . ?
C00C C00U C00X 105.6(4) . . ?
C00U C00X C00O 103.6(4) . . ?

_olex2_date_sample_data_collection 1569396252.0
_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 2.135
_oxdiff_exptl_absorpt_empirical_full_min 0.530
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1963665'
loop_
_audit_author_name
_audit_author_address
'Simon Herbert'
;HUAqiao
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2019-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H37 N O7'
_chemical_formula_sum            'C33 H37 N O7'
_chemical_formula_weight         559.63
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.4833(19)
_cell_length_b                   14.435(2)
_cell_length_c                   21.245(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3214.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.3650
_cell_measurement_theta_min      3.8490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_description       block
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.1332
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17567
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.351
_diffrn_reflns_theta_min         3.413
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                2618
_reflns_number_total             7044
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         7044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2473
_refine_ls_R_factor_gt           0.0864
_refine_ls_restrained_S_all      1.032
_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)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.2271
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00X(H00A,H00B,H00D), C00Z(H00H,H00I,H00M), C010(H01A,H01B,H01C), C012(H01F,
 H01G,H01H), C013(H01I,H01J,H01K), C014(H01L,H01M,H01N), C015(H01O,H01P,H01Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O00F(H00F)
;
_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 -0.7646(5) -0.2453(3) -0.6065(2) 0.0863(14) Uani 1 1 d . . . . .
O002 O -0.5703(5) -0.2032(4) -0.5758(2) 0.1019(17) Uani 1 1 d . . . . .
O003 O -0.5822(5) -0.4201(3) -0.5547(3) 0.1033(17) Uani 1 1 d . . . . .
O004 O -0.6876(6) 0.1022(4) -0.3700(3) 0.121(2) Uani 1 1 d . . . . .
C005 C -0.6748(7) -0.4007(4) -0.5242(3) 0.0662(17) Uani 1 1 d . . . . .
C006 C -0.7659(6) -0.4735(4) -0.5038(3) 0.0589(16) Uani 1 1 d . . . . .
C007 C -0.6985(6) -0.2979(4) -0.5079(3) 0.0588(16) Uani 1 1 d . . . . .
H007 H -0.788349 -0.289096 -0.496679 0.071 Uiso 1 1 calc R . . . .
C008 C -0.6388(6) -0.1695(4) -0.4314(3) 0.0633(16) Uani 1 1 d . . . . .
C009 C -0.6680(7) -0.2427(4) -0.5666(3) 0.0718(18) Uani 1 1 d . . . . .
O00A O -1.0037(7) -0.7630(5) -0.4792(4) 0.154(3) Uani 1 1 d . . . . .
C00B C -0.6198(6) -0.3363(4) -0.3988(3) 0.0621(16) Uani 1 1 d . . . . .
C00C C -0.6135(6) -0.2683(4) -0.4522(3) 0.0635(17) Uani 1 1 d . . . . .
H00C H -0.525419 -0.269737 -0.467708 0.076 Uiso 1 1 calc R . . . .
N00D N -1.0165(8) -0.6893(6) -0.4554(5) 0.129(3) Uani 1 1 d . . . . .
C00E C -0.8725(6) -0.4565(4) -0.4683(3) 0.0738(19) Uani 1 1 d . . . . .
H00E H -0.889394 -0.396305 -0.455078 0.089 Uiso 1 1 calc R . . . .
O00F O -0.6487(7) -0.5336(5) -0.2582(3) 0.141(2) Uani 1 1 d . . . . .
H00F H -0.581028 -0.561601 -0.254675 0.212 Uiso 1 1 calc GR . . . .
C00G C -0.7412(6) -0.5637(5) -0.5217(3) 0.0751(19) Uani 1 1 d . . . . .
H00G H -0.667758 -0.576970 -0.544578 0.090 Uiso 1 1 calc R . . . .
C00H C -0.9284(7) -0.6141(4) -0.4727(4) 0.078(2) Uani 1 1 d . . . . .
C00I C -0.6790(8) 0.0130(5) -0.3913(4) 0.080(2) Uani 1 1 d . . . . .
C00J C -0.5441(6) -0.1182(5) -0.4045(3) 0.076(2) Uani 1 1 d . . . . .
H00J H -0.463997 -0.144925 -0.399392 0.091 Uiso 1 1 calc R . . . .
C00K C -0.5382(7) -0.4126(5) -0.3979(3) 0.0776(19) Uani 1 1 d . . . . .
H00K H -0.475513 -0.417617 -0.428704 0.093 Uiso 1 1 calc R . . . .
C00L C -0.8241(8) -0.6345(4) -0.5063(4) 0.082(2) Uani 1 1 d . . . . .
H00L H -0.807792 -0.695082 -0.518893 0.098 Uiso 1 1 calc R . . . .
C00M C -0.5476(8) -0.4807(5) -0.3529(4) 0.083(2) Uani 1 1 d . . . . .
C00N C -0.9549(7) -0.5265(5) -0.4518(4) 0.088(2) Uani 1 1 d . . . . .
H00N H -1.026461 -0.514742 -0.427210 0.106 Uiso 1 1 calc R . . . .
C00O C -0.7437(10) -0.1998(8) -0.6673(4) 0.133(4) Uani 1 1 d . . . . .
H00O H -0.675343 -0.161100 -0.676655 0.160 Uiso 1 1 calc R . . . .
C00P C -0.7762(8) -0.0359(5) -0.4160(4) 0.102(3) Uani 1 1 d . . . . .
H00P H -0.856857 -0.009517 -0.419615 0.122 Uiso 1 1 calc R . . . .
C00Q C -0.7549(7) -0.1260(5) -0.4361(4) 0.087(2) Uani 1 1 d . . . . .
H00Q H -0.822629 -0.158611 -0.453644 0.105 Uiso 1 1 calc R . . . .
C00R C -0.7092(7) -0.3287(5) -0.3518(3) 0.077(2) Uani 1 1 d . . . . .
H00R H -0.763764 -0.277877 -0.351816 0.093 Uiso 1 1 calc R . . . .
C00S C -0.5622(8) -0.0293(5) -0.3846(4) 0.089(2) Uani 1 1 d . . . . .
H00S H -0.494985 0.003092 -0.366366 0.107 Uiso 1 1 calc R . . . .
C00T C -0.7213(7) -0.3943(6) -0.3040(4) 0.086(2) Uani 1 1 d . . . . .
C00U C -0.6389(9) -0.4692(6) -0.3061(4) 0.096(2) Uani 1 1 d . . . . .
C00V C -0.4599(10) -0.5676(6) -0.3558(5) 0.112(3) Uani 1 1 d . . . . .
O00W O -1.0940(10) -0.6747(5) -0.4170(7) 0.272(8) Uani 1 1 d . . . . .
C00X C -0.7973(10) 0.1512(6) -0.3839(5) 0.146(4) Uani 1 1 d . . . . .
H00A H -0.818184 0.143063 -0.427515 0.220 Uiso 1 1 calc GR . . . .
H00B H -0.783769 0.215733 -0.375373 0.220 Uiso 1 1 calc GR . . . .
H00D H -0.866280 0.128702 -0.358329 0.220 Uiso 1 1 calc GR . . . .
C00Y C -0.8232(9) -0.3818(8) -0.2523(4) 0.116(3) Uani 1 1 d . . . . .
C00Z C -0.3720(10) -0.5612(7) -0.4131(5) 0.146(4) Uani 1 1 d . . . . .
H00H H -0.422486 -0.554396 -0.450485 0.219 Uiso 1 1 calc GR . . . .
H00I H -0.321693 -0.616574 -0.416038 0.219 Uiso 1 1 calc GR . . . .
H00M H -0.316759 -0.508584 -0.408599 0.219 Uiso 1 1 calc GR . . . .
C010 C -0.8409(12) -0.2228(8) -0.7090(4) 0.160(5) Uani 1 1 d . . . . .
H01A H -0.826320 -0.192534 -0.748638 0.240 Uiso 1 1 calc GR . . . .
H01B H -0.921298 -0.203088 -0.692094 0.240 Uiso 1 1 calc GR . . . .
H01C H -0.842079 -0.288682 -0.715219 0.240 Uiso 1 1 calc GR . . . .
C011 C -0.3805(14) -0.5731(10) -0.2952(7) 0.166(6) Uani 1 1 d . . . . .
H01D H -0.316(15) -0.523(11) -0.287(8) 0.250 Uiso 1 1 d R . . . .
H01E H -0.320(15) -0.608(11) -0.298(8) 0.250 Uiso 1 1 d R . . . .
C012 C -0.5440(13) -0.6544(6) -0.3640(5) 0.162(5) Uani 1 1 d . . . . .
H01F H -0.604337 -0.657836 -0.330134 0.243 Uiso 1 1 calc GR . . . .
H01G H -0.491167 -0.708776 -0.363729 0.243 Uiso 1 1 calc GR . . . .
H01H H -0.588793 -0.650776 -0.403369 0.243 Uiso 1 1 calc GR . . . .
C013 C -0.8972(9) -0.2906(8) -0.2598(4) 0.141(4) Uani 1 1 d . . . . .
H01I H -0.838224 -0.239829 -0.262174 0.211 Uiso 1 1 calc GR . . . .
H01J H -0.952566 -0.282052 -0.224245 0.211 Uiso 1 1 calc GR . . . .
H01K H -0.947212 -0.292810 -0.297626 0.211 Uiso 1 1 calc GR . . . .
C014 C -0.7642(11) -0.3794(9) -0.1870(4) 0.171(5) Uani 1 1 d . . . . .
H01L H -0.726977 -0.438621 -0.177740 0.257 Uiso 1 1 calc GR . . . .
H01M H -0.828944 -0.365588 -0.156503 0.257 Uiso 1 1 calc GR . . . .
H01N H -0.699283 -0.332526 -0.185603 0.257 Uiso 1 1 calc GR . . . .
C015 C -0.9227(12) -0.4589(10) -0.2581(6) 0.190(6) Uani 1 1 d . . . . .
H01O H -0.961909 -0.456089 -0.298857 0.285 Uiso 1 1 calc GR . . . .
H01P H -0.986679 -0.450987 -0.226167 0.285 Uiso 1 1 calc GR . . . .
H01Q H -0.881999 -0.517937 -0.252767 0.285 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.321(8) . ?
O001 C00O 1.466(8) . ?
O002 C009 1.188(7) . ?
O003 C005 1.200(7) . ?
O004 C00I 1.368(8) . ?
O004 C00X 1.382(10) . ?
C005 C006 1.485(8) . ?
C005 C007 1.544(8) . ?
C006 C00E 1.370(8) . ?
C006 C00G 1.381(8) . ?
C007 C009 1.516(8) . ?
C007 C00C 1.541(8) . ?
C008 C00C 1.517(8) . ?
C008 C00J 1.364(8) . ?
C008 C00Q 1.373(8) . ?
O00A N00D 1.186(9) . ?
C00B C00C 1.502(8) . ?
C00B C00K 1.396(9) . ?
C00B C00R 1.374(9) . ?
N00D C00H 1.473(10) . ?
N00D O00W 1.170(11) . ?
C00E C00N 1.376(9) . ?
O00F C00U 1.382(8) . ?
C00G C00L 1.381(9) . ?
C00H C00L 1.338(9) . ?
C00H C00N 1.368(9) . ?
C00I C00P 1.346(9) . ?
C00I C00S 1.375(10) . ?
C00J C00S 1.365(9) . ?
C00K C00M 1.375(9) . ?
C00M C00U 1.390(11) . ?
C00M C00V 1.557(11) . ?
C00O C010 1.391(13) . ?
C00P C00Q 1.387(9) . ?
C00R C00T 1.393(9) . ?
C00T C00U 1.385(10) . ?
C00T C00Y 1.543(11) . ?
C00V C00Z 1.528(12) . ?
C00V C011 1.536(15) . ?
C00V C012 1.542(13) . ?
C00Y C013 1.537(12) . ?
C00Y C014 1.519(12) . ?
C00Y C015 1.531(14) . ?

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
C009 O001 C00O 116.0(6) . . ?
C00I O004 C00X 117.7(7) . . ?
O003 C005 C006 120.9(6) . . ?
O003 C005 C007 118.4(6) . . ?
C006 C005 C007 120.7(5) . . ?
C00E C006 C005 123.9(5) . . ?
C00E C006 C00G 118.3(5) . . ?
C00G C006 C005 117.8(6) . . ?
C009 C007 C005 106.7(5) . . ?
C009 C007 C00C 111.4(5) . . ?
C00C C007 C005 110.2(5) . . ?
C00J C008 C00C 120.3(6) . . ?
C00J C008 C00Q 115.3(6) . . ?
C00Q C008 C00C 124.3(6) . . ?
O001 C009 C007 110.6(5) . . ?
O002 C009 O001 124.7(7) . . ?
O002 C009 C007 124.7(7) . . ?
C00K C00B C00C 119.9(6) . . ?
C00R C00B C00C 121.9(6) . . ?
C00R C00B C00K 118.1(6) . . ?
C008 C00C C007 112.5(5) . . ?
C00B C00C C007 111.9(5) . . ?
C00B C00C C008 112.7(5) . . ?
O00A N00D C00H 118.9(9) . . ?
O00W N00D O00A 122.6(9) . . ?
O00W N00D C00H 118.4(9) . . ?
C006 C00E C00N 121.3(6) . . ?
C006 C00G C00L 120.9(6) . . ?
C00L C00H N00D 118.9(7) . . ?
C00L C00H C00N 122.9(6) . . ?
C00N C00H N00D 118.2(7) . . ?
O004 C00I C00S 116.2(7) . . ?
C00P C00I O004 125.0(7) . . ?
C00P C00I C00S 118.8(7) . . ?
C008 C00J C00S 122.6(7) . . ?
C00M C00K C00B 122.0(7) . . ?
C00H C00L C00G 118.5(6) . . ?
C00K C00M C00U 117.5(7) . . ?
C00K C00M C00V 120.4(8) . . ?
C00U C00M C00V 122.1(7) . . ?
C00H C00N C00E 118.0(6) . . ?
C010 C00O O001 110.2(8) . . ?
C00I C00P C00Q 119.3(7) . . ?
C008 C00Q C00P 123.3(7) . . ?
C00B C00R C00T 122.5(7) . . ?
C00J C00S C00I 120.6(7) . . ?
C00R C00T C00Y 120.1(8) . . ?
C00U C00T C00R 116.8(7) . . ?
C00U C00T C00Y 123.1(8) . . ?
O00F C00U C00M 119.9(8) . . ?
O00F C00U C00T 117.1(8) . . ?
C00T C00U C00M 123.0(7) . . ?
C00Z C00V C00M 109.8(7) . . ?
C00Z C00V C011 110.1(9) . . ?
C00Z C00V C012 107.7(9) . . ?
C011 C00V C00M 109.2(9) . . ?
C011 C00V C012 111.2(9) . . ?
C012 C00V C00M 108.8(8) . . ?
C013 C00Y C00T 112.1(8) . . ?
C014 C00Y C00T 111.8(8) . . ?
C014 C00Y C013 106.3(9) . . ?
C014 C00Y C015 111.5(9) . . ?
C015 C00Y C00T 109.3(8) . . ?
C015 C00Y C013 105.7(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_7492
_database_code_depnum_ccdc_archive 'CCDC 1963687'
loop_
_audit_author_name
_audit_author_address
hesongtao
;HUAqiao
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H35 O4 S'
_chemical_formula_sum            'C31 H39 O4 S'
_chemical_formula_weight         507.68
_chemical_absolute_configuration am
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   23.808(4)
_cell_length_b                   10.360(3)
_cell_length_c                   11.8065(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.046(15)
_cell_angle_gamma                90
_cell_volume                     2900.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2680
_cell_measurement_theta_min      4.2680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_unetI/netI     0.1631
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11710
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_min         3.436
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -24.00   1.00   10.00    --   15.65 -57.00 -60.00   27
  2  ω    -52.00  30.00   1.00   10.00    --   15.65 -57.00 -30.00   82
  3  ω     -7.00  23.00   1.00   10.00    --  -16.43 -99.00 -90.00   30
  4  ω    -17.00  55.00   1.00   10.00    --   15.65 -99.00  90.00   72
  5  ω    -50.00 -24.00   1.00   10.00    --   15.65 -77.00  90.00   26
  6  ω    -43.00 -13.00   1.00   10.00    --  -16.43  77.00 -60.00   30
  7  ω    -11.00  82.00   1.00   10.00    --   15.65  77.00-150.00   93
  8  ω      3.00  28.00   1.00   10.00    --   15.65  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288926000
_diffrn_orient_matrix_UB_12      0.0139351000
_diffrn_orient_matrix_UB_13      0.0042197000
_diffrn_orient_matrix_UB_21      -0.0075438000
_diffrn_orient_matrix_UB_22      -0.0501102000
_diffrn_orient_matrix_UB_23      -0.0395113000
_diffrn_orient_matrix_UB_31      -0.0003711000
_diffrn_orient_matrix_UB_32      -0.0445729000
_diffrn_orient_matrix_UB_33      0.0453772000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                2739
_reflns_number_total             6219
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6219
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1964
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      0.992
_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)+(0.1057P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2143
_refine_ls_wR_factor_ref         0.2670
_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. Restrained distances
 H00C-H00Z
 2 with sigma of 0.02
 H00C-H00X
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C009(H009)
3.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C00I(H00D,H00E), C00K(H00G,H00H), C00M(H00I,H00J), C00N(H00K,
 H00L)
3.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00F(H00F)
3.d Idealised Me refined as rotating group:
 C00Q(H00M,H00N,H00O), C00R(H00P,H00Q,H00R), C00U(H00S,H00T,H00U), C00V(H00V,
 H00W,H00X), C00W(H00Y,H,HA), C00X(H00Z,HB,HC), C00Y(H00,HD,HE)
3.e Idealised tetrahedral OH refined as rotating group:
 O00C(H00C)
;
_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
S001 S 0.44229(11) 0.3565(3) 0.1257(2) 0.0890(9) Uani 1 1 d . . . . .
O002 O 0.50870(18) 0.7191(7) 0.1523(3) 0.0565(15) Uani 1 1 d . . . . .
O003 O 0.5318(2) 0.7489(6) 0.3367(4) 0.0657(17) Uani 1 1 d . . . . .
O004 O 0.4001(2) 0.8637(7) 0.1190(5) 0.0685(16) Uani 1 1 d . . . . .
C005 C 0.4813(2) 0.4400(8) 0.3297(6) 0.0430(17) Uani 1 1 d . . . . .
H00A H 0.510302 0.504014 0.348789 0.052 Uiso 1 1 calc R . . . .
H00B H 0.457810 0.433480 0.392633 0.052 Uiso 1 1 calc R . . . .
C006 C 0.4973(3) 0.7313(9) 0.2604(6) 0.0491(18) Uani 1 1 d . . . . .
C007 C 0.4338(3) 0.7157(9) 0.2701(5) 0.0445(17) Uani 1 1 d . . . . .
C008 C 0.3334(3) 0.4753(9) 0.2909(5) 0.0478(19) Uani 1 1 d . . . . .
H008 H 0.361693 0.429678 0.333065 0.057 Uiso 1 1 calc R . . . .
C009 C 0.4111(2) 0.5946(8) 0.2030(5) 0.0404(18) Uani 1 1 d . . . . .
H009 H 0.413168 0.615501 0.122485 0.049 Uiso 1 1 calc R . . . .
C00A C 0.4467(3) 0.4781(8) 0.2249(5) 0.0413(17) Uani 1 1 d . . . . .
C00B C 0.3488(3) 0.5679(8) 0.2163(5) 0.0471(18) Uani 1 1 d . . . . .
O00C O 0.1816(2) 0.5002(9) 0.2611(8) 0.115(3) Uani 1 1 d . . . . .
H00C H 0.179562 0.466109 0.323264 0.172 Uiso 1 1 calc DGR . . . .
C00D C 0.5063(4) 0.3180(11) 0.3094(7) 0.070(3) Uani 1 1 d . . . . .
C00E C 0.4057(3) 0.8385(10) 0.2173(6) 0.056(2) Uani 1 1 d . . . . .
C00F C 0.3075(3) 0.6367(9) 0.1552(6) 0.053(2) Uani 1 1 d . . . . .
H00F H 0.317905 0.698333 0.103753 0.064 Uiso 1 1 calc R . . . .
C00G C 0.2623(3) 0.3414(11) 0.3884(7) 0.071(3) Uani 1 1 d . . . . .
C00H C 0.2379(3) 0.5246(10) 0.2452(8) 0.070(3) Uani 1 1 d . . . . .
C00I C 0.4216(3) 0.7247(11) 0.3935(5) 0.062(2) Uani 1 1 d . . . . .
H00D H 0.451677 0.685193 0.442336 0.074 Uiso 1 1 calc R . . . .
H00E H 0.386438 0.681307 0.405308 0.074 Uiso 1 1 calc R . . . .
C00J C 0.2513(3) 0.6183(10) 0.1671(7) 0.061(2) Uani 1 1 d . . . . .
C00K C 0.5675(3) 0.7233(10) 0.1301(6) 0.061(2) Uani 1 1 d . . . . .
H00G H 0.587576 0.782433 0.182964 0.074 Uiso 1 1 calc R . . . .
H00H H 0.570596 0.755316 0.053686 0.074 Uiso 1 1 calc R . . . .
C00L C 0.2778(3) 0.4469(10) 0.3062(6) 0.060(2) Uani 1 1 d . . . . .
C00M C 0.4174(4) 0.8677(12) 0.4191(7) 0.080(3) Uani 1 1 d . . . . .
H00I H 0.395189 0.882045 0.482960 0.096 Uiso 1 1 calc R . . . .
H00J H 0.454560 0.904712 0.436554 0.096 Uiso 1 1 calc R . . . .
C00N C 0.3892(4) 0.9255(12) 0.3131(8) 0.084(3) Uani 1 1 d . . . . .
H00K H 0.402218 1.013051 0.302825 0.101 Uiso 1 1 calc R . . . .
H00L H 0.348573 0.926667 0.315711 0.101 Uiso 1 1 calc R . . . .
C00O C 0.4877(4) 0.2614(10) 0.2063(10) 0.078(3) Uani 1 1 d . . . . .
C00P C 0.2055(4) 0.6996(12) 0.0969(8) 0.080(3) Uani 1 1 d . . . . .
C00Q C 0.3132(4) 0.2708(14) 0.4431(9) 0.103(4) Uani 1 1 d . . . . .
H00M H 0.333717 0.232548 0.385182 0.155 Uiso 1 1 calc GR . . . .
H00N H 0.301187 0.204466 0.492346 0.155 Uiso 1 1 calc GR . . . .
H00O H 0.337197 0.330620 0.486679 0.155 Uiso 1 1 calc GR . . . .
C00R C 0.5937(4) 0.5943(12) 0.1419(9) 0.089(3) Uani 1 1 d . . . . .
H00P H 0.572834 0.534766 0.091990 0.133 Uiso 1 1 calc GR . . . .
H00Q H 0.593243 0.565320 0.219024 0.133 Uiso 1 1 calc GR . . . .
H00R H 0.631889 0.598903 0.122263 0.133 Uiso 1 1 calc GR . . . .
C00U C 0.2314(5) 0.7958(14) 0.0205(11) 0.117(5) Uani 1 1 d . . . . .
H00S H 0.256839 0.851153 0.065631 0.176 Uiso 1 1 calc GR . . . .
H00T H 0.202182 0.846868 -0.018646 0.176 Uiso 1 1 calc GR . . . .
H00U H 0.251728 0.750519 -0.033907 0.176 Uiso 1 1 calc GR . . . .
C00V C 0.2322(5) 0.3990(15) 0.4878(10) 0.120(5) Uani 1 1 d . . . . .
H00V H 0.256447 0.392283 0.556946 0.179 Uiso 1 1 calc GR . . . .
H00W H 0.197931 0.352304 0.495732 0.179 Uiso 1 1 calc GR . . . .
H00X H 0.223550 0.488148 0.472445 0.179 Uiso 1 1 calc DGR . . . .
C00W C 0.1718(5) 0.7800(13) 0.1735(12) 0.114(4) Uani 1 1 d . . . . .
H00Y H 0.161144 0.727706 0.235275 0.171 Uiso 1 1 calc GR . . . .
H H 0.138549 0.812134 0.130855 0.171 Uiso 1 1 calc GR . . . .
HA H 0.194330 0.851222 0.203199 0.171 Uiso 1 1 calc GR . . . .
C00X C 0.2255(6) 0.2413(15) 0.3211(13) 0.131(5) Uani 1 1 d . . . . .
H00Z H 0.193940 0.283757 0.280871 0.197 Uiso 1 1 calc DGR . . . .
HB H 0.212221 0.178879 0.372507 0.197 Uiso 1 1 calc GR . . . .
HC H 0.247438 0.198694 0.267738 0.197 Uiso 1 1 calc GR . . . .
C00Y C 0.1673(5) 0.6090(15) 0.0228(12) 0.136(6) Uani 1 1 d . . . . .
H00 H 0.189363 0.563608 -0.028679 0.203 Uiso 1 1 calc GR . . . .
HD H 0.138591 0.658343 -0.019806 0.203 Uiso 1 1 calc GR . . . .
HE H 0.150048 0.548097 0.070221 0.203 Uiso 1 1 calc GR . . . .
C1 C 0.5401(7) 0.0653(15) 0.255(3) 0.173(12) Uani 1 1 d . . . . .
C2 C 0.5427(5) 0.2499(17) 0.3848(10) 0.123(6) Uani 1 1 d . . . . .
C3 C 0.5030(6) 0.1312(14) 0.1751(16) 0.133(6) Uani 1 1 d . . . . .
C4 C 0.5599(7) 0.129(2) 0.355(2) 0.162(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00A 1.717(8) . ?
S001 C00O 1.692(11) . ?
O002 C006 1.335(8) . ?
O002 C00K 1.448(8) . ?
O003 C006 1.179(8) . ?
O004 C00E 1.186(9) . ?
C005 C00A 1.479(9) . ?
C005 C00D 1.427(13) . ?
C006 C007 1.533(10) . ?
C007 C009 1.556(11) . ?
C007 C00E 1.543(12) . ?
C007 C00I 1.513(8) . ?
C008 C00B 1.373(11) . ?
C008 C00L 1.385(10) . ?
C009 C00A 1.485(10) . ?
C009 C00B 1.532(9) . ?
C00B C00F 1.368(10) . ?
O00C C00H 1.392(10) . ?
C00D C00O 1.389(13) . ?
C00D C2 1.379(13) . ?
C00E C00N 1.524(12) . ?
C00F C00J 1.370(10) . ?
C00G C00L 1.528(13) . ?
C00G C00Q 1.513(13) . ?
C00G C00V 1.548(15) . ?
C00G C00X 1.532(16) . ?
C00H C00J 1.395(13) . ?
C00H C00L 1.395(11) . ?
C00I C00M 1.517(15) . ?
C00J C00P 1.558(12) . ?
C00K C00R 1.475(14) . ?
C00M C00N 1.493(13) . ?
C00O C3 1.453(17) . ?
C00P C00U 1.512(15) . ?
C00P C00W 1.510(15) . ?
C00P C00Y 1.527(15) . ?
C1 C3 1.41(3) . ?
C1 C4 1.39(3) . ?
C2 C4 1.38(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00O S001 C00A 92.6(5) . . ?
C006 O002 C00K 116.9(5) . . ?
C00D C005 C00A 107.8(7) . . ?
O002 C006 C007 110.3(6) . . ?
O003 C006 O002 124.0(6) . . ?
O003 C006 C007 125.7(6) . . ?
C006 C007 C009 110.3(6) . . ?
C006 C007 C00E 106.2(6) . . ?
C00E C007 C009 109.9(5) . . ?
C00I C007 C006 109.9(5) . . ?
C00I C007 C009 116.9(7) . . ?
C00I C007 C00E 103.0(7) . . ?
C00B C008 C00L 122.9(7) . . ?
C00A C009 C007 113.6(5) . . ?
C00A C009 C00B 112.2(6) . . ?
C00B C009 C007 113.0(5) . . ?
C005 C00A S001 111.8(6) . . ?
C005 C00A C009 129.0(6) . . ?
C009 C00A S001 118.6(4) . . ?
C008 C00B C009 120.5(6) . . ?
C00F C00B C008 118.9(7) . . ?
C00F C00B C009 120.6(7) . . ?
C00O C00D C005 114.5(8) . . ?
C2 C00D C005 126.4(10) . . ?
C2 C00D C00O 118.9(11) . . ?
O004 C00E C007 125.8(8) . . ?
O004 C00E C00N 125.6(9) . . ?
C00N C00E C007 108.6(6) . . ?
C00B C00F C00J 122.4(8) . . ?
C00L C00G C00V 111.1(9) . . ?
C00L C00G C00X 108.3(8) . . ?
C00Q C00G C00L 112.8(7) . . ?
C00Q C00G C00V 105.6(9) . . ?
C00Q C00G C00X 107.1(10) . . ?
C00X C00G C00V 111.9(9) . . ?
O00C C00H C00J 119.6(8) . . ?
O00C C00H C00L 116.4(9) . . ?
C00J C00H C00L 123.9(8) . . ?
C007 C00I C00M 105.8(8) . . ?
C00F C00J C00H 116.5(7) . . ?
C00F C00J C00P 121.0(8) . . ?
C00H C00J C00P 122.5(7) . . ?
O002 C00K C00R 111.2(8) . . ?
C008 C00L C00G 121.5(7) . . ?
C008 C00L C00H 115.2(8) . . ?
C00H C00L C00G 123.3(7) . . ?
C00N C00M C00I 104.9(7) . . ?
C00M C00N C00E 105.0(8) . . ?
C00D C00O S001 112.7(7) . . ?
C00D C00O C3 123.0(12) . . ?
C3 C00O S001 124.1(11) . . ?
C00U C00P C00J 111.7(8) . . ?
C00U C00P C00Y 108.5(10) . . ?
C00W C00P C00J 111.3(8) . . ?
C00W C00P C00U 105.1(11) . . ?
C00W C00P C00Y 111.2(10) . . ?
C00Y C00P C00J 109.0(9) . . ?
C4 C1 C3 118.8(15) . . ?
C4 C2 C00D 118.9(16) . . ?
C1 C3 C00O 115.8(16) . . ?
C2 C4 C1 124.3(18) . . ?

_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 2.877
_oxdiff_exptl_absorpt_empirical_full_min 0.246
