# Electronic Supplementary Material (ESI) for ChemComm.
# 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_22019284_0m
_database_code_depnum_ccdc_archive 'CCDC 1935880'
loop_
_audit_author_name
_audit_author_address
'Wenli Wang'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-06-22 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_audit_creation_date             2019-04-01
_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         'C30 H42 O3'
_chemical_formula_sum            'C30 H42 O3'
_chemical_formula_weight         450.63
_chemical_absolute_configuration rmad
_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                   7.6085(10)
_cell_length_b                   18.276(3)
_cell_length_c                   18.693(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2599.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6509
_cell_measurement_temperature    298
_cell_measurement_theta_max      74.203
_cell_measurement_theta_min      6.280
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1266 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.9154. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.837
_diffrn_reflns_theta_min         3.382
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4974
_reflns_number_total             5309
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.152
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.022
_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)+(0.0494P)²+0.2126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0870
_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:
 C5(H5), C7(H7), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C4'(H4'A,H4'B), C2(H2A,H2B), C10'(H10A,H10B), C1'(H1'A,H1'B), C5'(H5'A,H5'B),
 C3(H3A,H3B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C2'(H2'), C6'(H6')
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C9'(H9'A,H9'B,
 H9'C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C8'(H8'A,H8'B,H8'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.48681(19) 0.43443(8) 0.63579(7) 0.0553(3) Uani 1 1 d . . . . .
H2 H 0.576370 0.410725 0.643416 0.083 Uiso 1 1 calc GR . . . .
O3 O 0.70882(18) 0.36616(8) 0.55376(8) 0.0605(4) Uani 1 1 d . . . . .
O1 O -0.16007(17) 0.52441(10) 0.45510(8) 0.0695(4) Uani 1 1 d . . . . .
C14 C 0.4173(2) 0.42021(9) 0.41677(9) 0.0401(3) Uani 1 1 d . . . . .
H14 H 0.389495 0.410302 0.369305 0.048 Uiso 1 1 calc R . . . .
C4' C 0.4322(3) 0.62868(10) 0.30910(10) 0.0495(4) Uani 1 1 d . . . . .
H4'A H 0.432443 0.672522 0.338356 0.059 Uiso 1 1 calc R . . . .
H4'B H 0.371286 0.640149 0.264928 0.059 Uiso 1 1 calc R . . . .
C3' C 0.3311(2) 0.56967(9) 0.34792(8) 0.0396(3) Uani 1 1 d . . . . .
C2' C 0.1949(2) 0.53625(9) 0.31778(9) 0.0434(4) Uani 1 1 d . . . . .
H2' H 0.163588 0.550865 0.271861 0.052 Uiso 1 1 calc R . . . .
C13 C 0.5459(2) 0.38063(9) 0.44648(9) 0.0418(4) Uani 1 1 d . . . . .
C12 C 0.5823(2) 0.39348(9) 0.52212(10) 0.0437(4) Uani 1 1 d . . . . .
C2 C 0.1554(3) 0.61727(11) 0.67609(11) 0.0569(5) Uani 1 1 d . . . . .
H2A H 0.078744 0.585587 0.703640 0.068 Uiso 1 1 calc R . . . .
H2B H 0.219563 0.648084 0.709316 0.068 Uiso 1 1 calc R . . . .
C16 C 0.6228(4) 0.24766(12) 0.43613(16) 0.0759(7) Uani 1 1 d . . . . .
H16A H 0.644592 0.246377 0.486703 0.114 Uiso 1 1 calc GR . . . .
H16B H 0.699086 0.213522 0.412479 0.114 Uiso 1 1 calc GR . . . .
H16C H 0.502618 0.234662 0.427015 0.114 Uiso 1 1 calc GR . . . .
C10' C 0.3938(2) 0.55195(8) 0.42205(8) 0.0374(3) Uani 1 1 d . . . . .
H10A H 0.363932 0.592254 0.453540 0.045 Uiso 1 1 calc R . . . .
H10B H 0.520869 0.547628 0.421361 0.045 Uiso 1 1 calc R . . . .
C1' C 0.0879(2) 0.47711(10) 0.35164(9) 0.0442(4) Uani 1 1 d . . . . .
H1'A H 0.117329 0.430731 0.329446 0.053 Uiso 1 1 calc R . . . .
H1'B H -0.035592 0.486581 0.342617 0.053 Uiso 1 1 calc R . . . .
C5' C 0.6228(3) 0.60845(12) 0.29133(11) 0.0554(5) Uani 1 1 d . . . . .
H5'A H 0.692617 0.609688 0.334741 0.066 Uiso 1 1 calc R . . . .
H5'B H 0.626564 0.559001 0.272546 0.066 Uiso 1 1 calc R . . . .
C3 C 0.0458(3) 0.66474(11) 0.62706(13) 0.0605(5) Uani 1 1 d . . . . .
H3A H 0.122762 0.698974 0.602746 0.073 Uiso 1 1 calc R . . . .
H3B H -0.035670 0.692980 0.655884 0.073 Uiso 1 1 calc R . . . .
C5 C 0.0704(2) 0.56859(9) 0.53173(9) 0.0401(3) Uani 1 1 d . . . . .
H5 H 0.152455 0.601336 0.507081 0.048 Uiso 1 1 calc R . . . .
C1 C 0.2844(2) 0.57091(10) 0.63377(10) 0.0465(4) Uani 1 1 d . . . . .
H1A H 0.353512 0.541677 0.666721 0.056 Uiso 1 1 calc R . . . .
H1B H 0.364357 0.602875 0.608120 0.056 Uiso 1 1 calc R . . . .
C7 C 0.11713(19) 0.47105(9) 0.43250(8) 0.0384(3) Uani 1 1 d . . . . .
H7 H 0.082680 0.421266 0.446030 0.046 Uiso 1 1 calc R . . . .
C11 C 0.4586(2) 0.43887(9) 0.56373(9) 0.0409(3) Uani 1 1 d . . . . .
C7' C 0.8395(3) 0.70363(11) 0.24405(12) 0.0552(5) Uani 1 1 d . . . . .
C15 C 0.6581(3) 0.32496(11) 0.40772(11) 0.0523(4) Uani 1 1 d . . . . .
H15 H 0.781134 0.336557 0.418309 0.063 Uiso 1 1 calc R . . . .
C8 C 0.31381(19) 0.47940(8) 0.45358(8) 0.0350(3) Uani 1 1 d . . . . .
C6 C -0.0069(2) 0.52269(10) 0.47219(9) 0.0433(4) Uani 1 1 d . . . . .
C4 C -0.0591(2) 0.62178(11) 0.57060(11) 0.0521(4) Uani 1 1 d . . . . .
C6' C 0.7003(3) 0.65990(11) 0.23762(11) 0.0550(5) Uani 1 1 d . . . . .
H6' H 0.643336 0.661581 0.193635 0.066 Uiso 1 1 calc R . . . .
C9 C 0.32946(19) 0.47882(8) 0.53401(8) 0.0360(3) Uani 1 1 d . . . . .
C20 C 0.0859(3) 0.45940(10) 0.61857(10) 0.0493(4) Uani 1 1 d . . . . .
H20A H 0.012654 0.481363 0.654450 0.074 Uiso 1 1 calc GR . . . .
H20B H 0.165248 0.425452 0.640759 0.074 Uiso 1 1 calc GR . . . .
H20C H 0.013744 0.433989 0.584539 0.074 Uiso 1 1 calc GR . . . .
C19 C -0.2188(3) 0.58522(15) 0.60619(15) 0.0711(6) Uani 1 1 d . . . . .
H19A H -0.180266 0.556564 0.646269 0.107 Uiso 1 1 calc GR . . . .
H19B H -0.276636 0.554074 0.572184 0.107 Uiso 1 1 calc GR . . . .
H19C H -0.299179 0.622192 0.622320 0.107 Uiso 1 1 calc GR . . . .
C9' C 0.8958(3) 0.75154(13) 0.18244(15) 0.0757(7) Uani 1 1 d . . . . .
H9'A H 1.007872 0.735368 0.164949 0.114 Uiso 1 1 calc GR . . . .
H9'B H 0.904923 0.801326 0.198396 0.114 Uiso 1 1 calc GR . . . .
H9'C H 0.810362 0.748425 0.144762 0.114 Uiso 1 1 calc GR . . . .
C10 C 0.1923(2) 0.51967(8) 0.57980(8) 0.0377(3) Uani 1 1 d . . . . .
C18 C -0.1283(3) 0.67807(13) 0.51591(15) 0.0751(7) Uani 1 1 d . . . . .
H18A H -0.189466 0.716419 0.540632 0.113 Uiso 1 1 calc GR . . . .
H18B H -0.207085 0.654323 0.483222 0.113 Uiso 1 1 calc GR . . . .
H18C H -0.031223 0.698499 0.489861 0.113 Uiso 1 1 calc GR . . . .
C17 C 0.6363(4) 0.32798(16) 0.32687(13) 0.0769(7) Uani 1 1 d . . . . .
H17A H 0.516803 0.316796 0.314572 0.115 Uiso 1 1 calc GR . . . .
H17B H 0.713276 0.292905 0.304951 0.115 Uiso 1 1 calc GR . . . .
H17C H 0.665154 0.376146 0.310074 0.115 Uiso 1 1 calc GR . . . .
C8' C 0.9499(3) 0.70905(15) 0.30986(18) 0.0828(8) Uani 1 1 d . . . . .
H8'A H 0.899572 0.679339 0.346940 0.124 Uiso 1 1 calc GR . . . .
H8'B H 0.954326 0.759060 0.325461 0.124 Uiso 1 1 calc GR . . . .
H8'C H 1.066655 0.692228 0.299512 0.124 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
O2 H2 0.8200 . ?
O2 C11 1.366(2) . ?
O3 C12 1.235(2) . ?
O1 C6 1.209(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.337(2) . ?
C14 C8 1.505(2) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' C3' 1.510(2) . ?
C4' C5' 1.533(3) . ?
C3' C2' 1.329(2) . ?
C3' C10' 1.501(2) . ?
C2' H2' 0.9300 . ?
C2' C1' 1.494(3) . ?
C13 C12 1.460(3) . ?
C13 C15 1.513(2) . ?
C12 C11 1.476(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.513(3) . ?
C2 C1 1.519(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C15 1.533(3) . ?
C10' H10A 0.9700 . ?
C10' H10B 0.9700 . ?
C10' C8 1.574(2) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C7 1.532(2) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C5' C6' 1.497(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.539(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.513(2) . ?
C5 C4 1.563(2) . ?
C5 C10 1.571(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C10 1.545(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.555(2) . ?
C7 C6 1.527(2) . ?
C11 C9 1.344(2) . ?
C7' C6' 1.332(3) . ?
C7' C9' 1.509(3) . ?
C7' C8' 1.493(4) . ?
C15 H15 0.9800 . ?
C15 C17 1.521(3) . ?
C8 C9 1.508(2) . ?
C4 C19 1.538(3) . ?
C4 C18 1.543(3) . ?
C6' H6' 0.9300 . ?
C9 C10 1.542(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C10 1.547(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 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
C11 O2 H2 109.5 . . ?
C13 C14 H14 117.2 . . ?
C13 C14 C8 125.58(15) . . ?
C8 C14 H14 117.2 . . ?
H4'A C4' H4'B 107.6 . . ?
C3' C4' H4'A 108.7 . . ?
C3' C4' H4'B 108.7 . . ?
C3' C4' C5' 114.43(15) . . ?
C5' C4' H4'A 108.7 . . ?
C5' C4' H4'B 108.7 . . ?
C2' C3' C4' 121.45(15) . . ?
C2' C3' C10' 122.71(15) . . ?
C10' C3' C4' 115.84(15) . . ?
C3' C2' H2' 117.3 . . ?
C3' C2' C1' 125.32(15) . . ?
C1' C2' H2' 117.3 . . ?
C14 C13 C12 117.00(15) . . ?
C14 C13 C15 125.29(16) . . ?
C12 C13 C15 117.70(15) . . ?
O3 C12 C13 123.14(17) . . ?
O3 C12 C11 118.15(16) . . ?
C13 C12 C11 118.67(14) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C3 C2 C1 111.14(17) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C3' C10' H10A 108.8 . . ?
C3' C10' H10B 108.8 . . ?
C3' C10' C8 113.88(13) . . ?
H10A C10' H10B 107.7 . . ?
C8 C10' H10A 108.8 . . ?
C8 C10' H10B 108.8 . . ?
C2' C1' H1'A 109.0 . . ?
C2' C1' H1'B 109.0 . . ?
C2' C1' C7 113.03(13) . . ?
H1'A C1' H1'B 107.8 . . ?
C7 C1' H1'A 109.0 . . ?
C7 C1' H1'B 109.0 . . ?
C4' C5' H5'A 109.3 . . ?
C4' C5' H5'B 109.3 . . ?
H5'A C5' H5'B 108.0 . . ?
C6' C5' C4' 111.49(17) . . ?
C6' C5' H5'A 109.3 . . ?
C6' C5' H5'B 109.3 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C2 C3 C4 114.14(16) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C6 C5 H5 103.9 . . ?
C6 C5 C4 116.21(14) . . ?
C6 C5 C10 109.57(13) . . ?
C4 C5 H5 103.9 . . ?
C4 C5 C10 117.41(14) . . ?
C10 C5 H5 103.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C2 C1 C10 112.65(14) . . ?
H1A C1 H1B 107.8 . . ?
C10 C1 H1A 109.1 . . ?
C10 C1 H1B 109.1 . . ?
C1' C7 H7 106.4 . . ?
C1' C7 C8 112.51(13) . . ?
C8 C7 H7 106.4 . . ?
C6 C7 C1' 110.17(13) . . ?
C6 C7 H7 106.4 . . ?
C6 C7 C8 114.26(13) . . ?
O2 C11 C12 112.70(14) . . ?
C9 C11 O2 123.68(15) . . ?
C9 C11 C12 123.60(15) . . ?
C6' C7' C9' 120.3(2) . . ?
C6' C7' C8' 124.1(2) . . ?
C8' C7' C9' 115.5(2) . . ?
C13 C15 C16 110.80(17) . . ?
C13 C15 H15 107.3 . . ?
C13 C15 C17 112.94(16) . . ?
C16 C15 H15 107.3 . . ?
C17 C15 C16 111.01(19) . . ?
C17 C15 H15 107.3 . . ?
C14 C8 C10' 103.42(12) . . ?
C14 C8 C7 108.49(12) . . ?
C14 C8 C9 114.17(13) . . ?
C7 C8 C10' 111.10(12) . . ?
C9 C8 C10' 110.41(12) . . ?
C9 C8 C7 109.15(12) . . ?
O1 C6 C5 123.71(17) . . ?
O1 C6 C7 118.91(16) . . ?
C5 C6 C7 117.38(13) . . ?
C3 C4 C5 108.00(15) . . ?
C3 C4 C18 106.92(18) . . ?
C19 C4 C3 109.57(19) . . ?
C19 C4 C5 115.40(16) . . ?
C19 C4 C18 107.88(19) . . ?
C18 C4 C5 108.76(17) . . ?
C5' C6' H6' 115.5 . . ?
C7' C6' C5' 129.0(2) . . ?
C7' C6' H6' 115.5 . . ?
C11 C9 C8 118.27(14) . . ?
C11 C9 C10 121.87(14) . . ?
C8 C9 C10 119.76(13) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C1 C10 C5 107.25(13) . . ?
C1 C10 C20 111.29(14) . . ?
C9 C10 C5 110.95(13) . . ?
C9 C10 C1 110.42(12) . . ?
C9 C10 C20 105.62(13) . . ?
C20 C10 C5 111.35(13) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?

_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_22019691tdb381_0m
_database_code_depnum_ccdc_archive 'CCDC 1935884'
loop_
_audit_author_name
_audit_author_address
'Wenli Wang'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-06-22 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_audit_creation_date             2019-06-15
_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         'C30 H42 O3'
_chemical_formula_sum            'C30 H42 O3'
_chemical_formula_weight         450.63
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2640(3)
_cell_length_b                   12.5469(3)
_cell_length_c                   20.5284(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.8070(10)
_cell_angle_gamma                90
_cell_volume                     2587.74(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.428
_cell_measurement_theta_min      4.154
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.8489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1162 before and 0.0642 after correction. The Ratio of minimum to maximum transmission is 0.9140. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35509
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.696
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.782
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                8634
_reflns_number_total             9039
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.201
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 3309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9039
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.036
_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)+(0.0532P)²+0.4001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0920
_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:
 C27(H27), C7(H7), C15(H15), C35(H35), C25(H25), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C10'(H10A,H10B), C41(H41A,H41B), C21(H21A,H21B), C1'(H1'A,
 H1'B), C50(H50A,H50B), C2(H2A,H2B), C45(H45A,H45B), C4'(H4'A,H4'B), C3(H3A,
 H3B), C1(H1A,H1B), C5'(H5'A,H5'B), C44(H44A,H44B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C42(H42), C2'(H2'), C14(H14), C46(H46), C34(H34)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C19(H19A,H19B,H19C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,
 H20B,H20C), C9'(H9'A,H9'B,H9'C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C8'(H8'A,H8'B,H8'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O6 O 0.69360(15) 0.86761(13) 0.71628(8) 0.0236(3) Uani 1 1 d . . . . .
O1 O 1.06880(17) 0.13726(14) 0.89000(8) 0.0273(4) Uani 1 1 d . . . . .
O3 O 1.12183(15) 0.36830(14) 0.57001(7) 0.0225(3) Uani 1 1 d . . . . .
O4 O 0.36889(15) 0.48819(14) 0.59186(8) 0.0219(3) Uani 1 1 d . . . . .
O2 O 1.21126(15) 0.44628(13) 0.68904(8) 0.0223(3) Uani 1 1 d . . . . .
H2 H 1.238473 0.450468 0.653218 0.033 Uiso 1 1 calc GR . . . .
O5 O 0.38247(15) 0.48331(14) 0.46843(8) 0.0257(4) Uani 1 1 d . . . . .
C6 C 1.03659(19) 0.20250(19) 0.84627(10) 0.0194(4) Uani 1 1 d . . . . .
C22 C 0.5551(2) 0.51378(18) 0.80149(10) 0.0207(4) Uani 1 1 d . . . . .
H22A H 0.474896 0.551072 0.809600 0.025 Uiso 1 1 calc R . . . .
H22B H 0.556894 0.441652 0.821205 0.025 Uiso 1 1 calc R . . . .
C10' C 0.8681(2) 0.08798(18) 0.77438(10) 0.0182(4) Uani 1 1 d . . . . .
H10A H 0.850771 0.046110 0.732619 0.022 Uiso 1 1 calc R . . . .
H10B H 0.891578 0.037482 0.812012 0.022 Uiso 1 1 calc R . . . .
C29 C 0.56561(19) 0.59569(17) 0.61901(10) 0.0163(4) Uani 1 1 d . . . . .
C41 C 0.81396(19) 0.58429(18) 0.62043(10) 0.0174(4) Uani 1 1 d . . . . .
H41A H 0.806911 0.546403 0.661870 0.021 Uiso 1 1 calc R . . . .
H41B H 0.824076 0.529851 0.586908 0.021 Uiso 1 1 calc R . . . .
C6' C 0.6055(2) 0.0343(2) 0.92730(11) 0.0226(4) Uani 1 1 d . . . . .
H6' H 0.585901 -0.038738 0.917711 0.027 Uiso 1 1 calc R . . . .
C11 C 1.11297(19) 0.37132(18) 0.68287(10) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.95138(19) 0.25551(17) 0.72279(10) 0.0160(4) Uani 1 1 d . . . . .
C3' C 0.7437(2) 0.14786(18) 0.78038(10) 0.0180(4) Uani 1 1 d . . . . .
C27 C 0.69083(19) 0.76513(17) 0.61856(10) 0.0162(4) Uani 1 1 d . . . . .
H27 H 0.611472 0.803238 0.592498 0.019 Uiso 1 1 calc R . . . .
C42 C 0.93709(19) 0.65292(19) 0.63409(10) 0.0176(4) Uani 1 1 d . . . . .
H42 H 1.019787 0.617929 0.649358 0.021 Uiso 1 1 calc R . . . .
C40 C 0.4191(2) 0.67558(18) 0.68845(11) 0.0195(4) Uani 1 1 d . . . . .
H40A H 0.429805 0.748692 0.673593 0.029 Uiso 1 1 calc GR . . . .
H40B H 0.397318 0.677002 0.732756 0.029 Uiso 1 1 calc GR . . . .
H40C H 0.346984 0.640537 0.657081 0.029 Uiso 1 1 calc GR . . . .
C2' C 0.7233(2) 0.24754(19) 0.75903(10) 0.0194(4) Uani 1 1 d . . . . .
H2' H 0.642468 0.280337 0.763977 0.023 Uiso 1 1 calc R . . . .
C21 C 0.5476(2) 0.50436(17) 0.72669(10) 0.0183(4) Uani 1 1 d . . . . .
H21A H 0.464610 0.466487 0.706357 0.022 Uiso 1 1 calc R . . . .
H21B H 0.623421 0.460730 0.719034 0.022 Uiso 1 1 calc R . . . .
C7' C 0.5448(2) 0.0789(2) 0.97131(11) 0.0250(5) Uani 1 1 d . . . . .
C1' C 0.81661(19) 0.31324(18) 0.72771(10) 0.0171(4) Uani 1 1 d . . . . .
H1'A H 0.838058 0.379517 0.753877 0.020 Uiso 1 1 calc R . . . .
H1'B H 0.770123 0.333858 0.682347 0.020 Uiso 1 1 calc R . . . .
C13 C 0.9726(2) 0.24358(18) 0.60269(10) 0.0183(4) Uani 1 1 d . . . . .
C31 C 0.4745(2) 0.54040(18) 0.57535(11) 0.0183(4) Uani 1 1 d . . . . .
C50 C 0.81418(19) 0.82202(18) 0.60437(10) 0.0172(4) Uani 1 1 d . . . . .
H50A H 0.801349 0.835839 0.555998 0.021 Uiso 1 1 calc R . . . .
H50B H 0.823949 0.891690 0.627503 0.021 Uiso 1 1 calc R . . . .
C7 C 0.9857(2) 0.16374(17) 0.77438(10) 0.0167(4) Uani 1 1 d . . . . .
H7 H 1.058566 0.120803 0.761552 0.020 Uiso 1 1 calc R . . . .
C15 C 0.9281(2) 0.2023(2) 0.53211(10) 0.0218(4) Uani 1 1 d . . . . .
H15 H 0.985733 0.236369 0.504178 0.026 Uiso 1 1 calc R . . . .
C19 C 1.2073(2) 0.3238(2) 0.97213(11) 0.0277(5) Uani 1 1 d . . . . .
H19A H 1.280833 0.360934 0.958044 0.041 Uiso 1 1 calc GR . . . .
H19B H 1.216522 0.246815 0.966353 0.041 Uiso 1 1 calc GR . . . .
H19C H 1.209203 0.339418 1.019093 0.041 Uiso 1 1 calc GR . . . .
C24 C 0.6862(2) 0.68822(19) 0.80720(10) 0.0199(4) Uani 1 1 d . . . . .
C26 C 0.68628(18) 0.77854(18) 0.69242(10) 0.0172(4) Uani 1 1 d . . . . .
C43 C 0.94018(19) 0.75816(18) 0.62666(10) 0.0175(4) Uani 1 1 d . . . . .
C28 C 0.68062(19) 0.64756(18) 0.59454(10) 0.0163(4) Uani 1 1 d . . . . .
C2 C 1.1567(2) 0.5339(2) 0.88428(11) 0.0272(5) Uani 1 1 d . . . . .
H2A H 1.251059 0.515883 0.902356 0.033 Uiso 1 1 calc R . . . .
H2B H 1.147728 0.612447 0.884891 0.033 Uiso 1 1 calc R . . . .
C45 C 1.0848(2) 0.91294(19) 0.68489(10) 0.0214(4) Uani 1 1 d . . . . .
H45A H 1.167140 0.952697 0.682665 0.026 Uiso 1 1 calc R . . . .
H45B H 1.008835 0.962425 0.671929 0.026 Uiso 1 1 calc R . . . .
C38 C 0.8260(2) 0.7332(2) 0.83649(11) 0.0247(5) Uani 1 1 d . . . . .
H38A H 0.829373 0.808657 0.824626 0.037 Uiso 1 1 calc GR . . . .
H38B H 0.892842 0.693540 0.818390 0.037 Uiso 1 1 calc GR . . . .
H38C H 0.844520 0.725925 0.885044 0.037 Uiso 1 1 calc GR . . . .
C39 C 0.5839(2) 0.7609(2) 0.83092(11) 0.0252(5) Uani 1 1 d . . . . .
H39A H 0.613052 0.774867 0.878655 0.038 Uiso 1 1 calc GR . . . .
H39B H 0.496960 0.725513 0.822741 0.038 Uiso 1 1 calc GR . . . .
H39C H 0.576757 0.828394 0.806448 0.038 Uiso 1 1 calc GR . . . .
C30 C 0.55042(19) 0.61315(17) 0.69149(10) 0.0162(4) Uani 1 1 d . . . . .
C9 C 1.06392(19) 0.33571(17) 0.73487(10) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.92306(19) 0.20875(18) 0.65410(10) 0.0182(4) Uani 1 1 d . . . . .
H14 H 0.864819 0.149159 0.646511 0.022 Uiso 1 1 calc R . . . .
C16 C 0.7845(2) 0.2373(2) 0.50458(12) 0.0307(5) Uani 1 1 d . . . . .
H16A H 0.726014 0.206951 0.531986 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.756522 0.212133 0.458659 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.779090 0.315269 0.505484 0.046 Uiso 1 1 calc GR . . . .
C4' C 0.6471(2) 0.09188(19) 0.81508(10) 0.0208(4) Uani 1 1 d . . . . .
H4'A H 0.630116 0.019047 0.796744 0.025 Uiso 1 1 calc R . . . .
H4'B H 0.561441 0.130928 0.806547 0.025 Uiso 1 1 calc R . . . .
C12 C 1.0700(2) 0.33046(18) 0.61433(10) 0.0177(4) Uani 1 1 d . . . . .
C4 C 1.0741(2) 0.3618(2) 0.92957(10) 0.0228(5) Uani 1 1 d . . . . .
C3 C 1.0696(2) 0.4843(2) 0.92820(11) 0.0270(5) Uani 1 1 d . . . . .
H3A H 0.976459 0.507473 0.911956 0.032 Uiso 1 1 calc R . . . .
H3B H 1.098913 0.511343 0.974171 0.032 Uiso 1 1 calc R . . . .
C47 C 1.1794(2) 0.90764(19) 0.80901(11) 0.0228(5) Uani 1 1 d . . . . .
C32 C 0.47203(19) 0.53550(18) 0.50350(11) 0.0195(4) Uani 1 1 d . . . . .
C10 C 1.1239(2) 0.37179(18) 0.80670(10) 0.0181(4) Uani 1 1 d . . . . .
C17 C 0.9444(3) 0.0821(2) 0.52771(12) 0.0305(5) Uani 1 1 d . . . . .
H17A H 1.036392 0.062445 0.547424 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.923401 0.060047 0.480936 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.883802 0.046471 0.551937 0.046 Uiso 1 1 calc GR . . . .
C35 C 0.5566(2) 0.5944(2) 0.40147(11) 0.0232(5) Uani 1 1 d . . . . .
H35 H 0.459983 0.601965 0.380829 0.028 Uiso 1 1 calc R . . . .
C1 C 1.1173(2) 0.49391(19) 0.81249(10) 0.0218(4) Uani 1 1 d . . . . .
H1A H 1.177175 0.526366 0.785877 0.026 Uiso 1 1 calc R . . . .
H1B H 1.025473 0.517829 0.793385 0.026 Uiso 1 1 calc R . . . .
C18 C 0.9621(2) 0.3226(2) 0.96349(11) 0.0306(5) Uani 1 1 d . . . . .
H18A H 0.967670 0.244970 0.968664 0.046 Uiso 1 1 calc GR . . . .
H18B H 0.875545 0.341835 0.936014 0.046 Uiso 1 1 calc GR . . . .
H18C H 0.971802 0.356033 1.007365 0.046 Uiso 1 1 calc GR . . . .
C46 C 1.0914(2) 0.8774(2) 0.75492(11) 0.0229(4) Uani 1 1 d . . . . .
H46 H 1.025657 0.827723 0.761738 0.028 Uiso 1 1 calc R . . . .
C34 C 0.6643(2) 0.64846(18) 0.51996(10) 0.0179(4) Uani 1 1 d . . . . .
H34 H 0.726845 0.689092 0.502106 0.021 Uiso 1 1 calc R . . . .
C5' C 0.7017(2) 0.0851(2) 0.89075(11) 0.0305(5) Uani 1 1 d . . . . .
H5'A H 0.785373 0.043525 0.899063 0.037 Uiso 1 1 calc R . . . .
H5'B H 0.722791 0.157900 0.908442 0.037 Uiso 1 1 calc R . . . .
C25 C 0.67260(19) 0.67746(17) 0.73069(10) 0.0166(4) Uani 1 1 d . . . . .
H25 H 0.751411 0.633717 0.725699 0.020 Uiso 1 1 calc R . . . .
C44 C 1.0690(2) 0.8202(2) 0.63463(11) 0.0215(4) Uani 1 1 d . . . . .
H44A H 1.075968 0.849278 0.590635 0.026 Uiso 1 1 calc R . . . .
H44B H 1.144048 0.770187 0.648587 0.026 Uiso 1 1 calc R . . . .
C33 C 0.5699(2) 0.59733(18) 0.47641(10) 0.0195(4) Uani 1 1 d . . . . .
C5 C 1.04248(19) 0.32168(18) 0.85617(10) 0.0178(4) Uani 1 1 d . . . . .
H5 H 0.949051 0.345899 0.838686 0.021 Uiso 1 1 calc R . . . .
C20 C 1.2702(2) 0.33141(19) 0.82238(11) 0.0218(4) Uani 1 1 d . . . . .
H20A H 1.271117 0.253763 0.827625 0.033 Uiso 1 1 calc GR . . . .
H20B H 1.318090 0.364413 0.863657 0.033 Uiso 1 1 calc GR . . . .
H20C H 1.313723 0.350614 0.785741 0.033 Uiso 1 1 calc GR . . . .
C9' C 0.4488(2) 0.0158(3) 1.00273(12) 0.0356(6) Uani 1 1 d . . . . .
H9'A H 0.360642 0.049039 0.991964 0.053 Uiso 1 1 calc GR . . . .
H9'B H 0.480309 0.014488 1.051125 0.053 Uiso 1 1 calc GR . . . .
H9'C H 0.443137 -0.057316 0.985514 0.053 Uiso 1 1 calc GR . . . .
C23 C 0.6792(2) 0.5750(2) 0.83479(10) 0.0226(5) Uani 1 1 d . . . . .
H23A H 0.758910 0.534807 0.828831 0.027 Uiso 1 1 calc R . . . .
H23B H 0.681300 0.579591 0.883138 0.027 Uiso 1 1 calc R . . . .
C48 C 1.1700(3) 0.8675(2) 0.87680(12) 0.0348(6) Uani 1 1 d . . . . .
H48A H 1.155965 0.927786 0.904961 0.052 Uiso 1 1 calc GR . . . .
H48B H 1.252797 0.830867 0.896910 0.052 Uiso 1 1 calc GR . . . .
H48C H 1.095191 0.817795 0.872796 0.052 Uiso 1 1 calc GR . . . .
C49 C 1.2919(2) 0.9845(2) 0.80896(12) 0.0290(5) Uani 1 1 d . . . . .
H49A H 1.376940 0.946704 0.821202 0.043 Uiso 1 1 calc GR . . . .
H49B H 1.288419 1.041484 0.841208 0.043 Uiso 1 1 calc GR . . . .
H49C H 1.283554 1.015348 0.764444 0.043 Uiso 1 1 calc GR . . . .
C36 C 0.6028(3) 0.4859(2) 0.38053(12) 0.0319(6) Uani 1 1 d . . . . .
H36A H 0.698456 0.477623 0.398312 0.048 Uiso 1 1 calc GR . . . .
H36B H 0.585467 0.481513 0.331855 0.048 Uiso 1 1 calc GR . . . .
H36C H 0.554189 0.429025 0.398036 0.048 Uiso 1 1 calc GR . . . .
C37 C 0.6309(3) 0.6837(2) 0.37457(12) 0.0378(6) Uani 1 1 d . . . . .
H37A H 0.601418 0.752582 0.388821 0.057 Uiso 1 1 calc GR . . . .
H37B H 0.612329 0.680494 0.325848 0.057 Uiso 1 1 calc GR . . . .
H37C H 0.726711 0.675514 0.391719 0.057 Uiso 1 1 calc GR . . . .
C8' C 0.5632(3) 0.1922(3) 0.99520(17) 0.0447(7) Uani 1 1 d . . . . .
H8'A H 0.631492 0.226606 0.975341 0.067 Uiso 1 1 calc GR . . . .
H8'B H 0.591150 0.193087 1.043793 0.067 Uiso 1 1 calc GR . . . .
H8'C H 0.478959 0.230924 0.982039 0.067 Uiso 1 1 calc GR . . . .
H4 H 0.329(4) 0.462(3) 0.5547(18) 0.050(10) 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
O6 C26 1.216(3) . ?
O1 C6 1.210(3) . ?
O3 C12 1.239(3) . ?
O4 C31 1.367(3) . ?
O2 C11 1.366(3) . ?
O5 C32 1.233(3) . ?
C6 C7 1.540(3) . ?
C6 C5 1.509(3) . ?
C22 C21 1.526(3) . ?
C22 C23 1.525(3) . ?
C10' C3' 1.508(3) . ?
C10' C7 1.536(3) . ?
C29 C31 1.348(3) . ?
C29 C28 1.520(3) . ?
C29 C30 1.543(3) . ?
C41 C42 1.507(3) . ?
C41 C28 1.577(3) . ?
C6' C7' 1.323(3) . ?
C6' C5' 1.499(3) . ?
C11 C9 1.346(3) . ?
C11 C12 1.478(3) . ?
C8 C1' 1.583(3) . ?
C8 C7 1.555(3) . ?
C8 C9 1.514(3) . ?
C8 C14 1.500(3) . ?
C3' C2' 1.328(3) . ?
C3' C4' 1.508(3) . ?
C27 C50 1.532(3) . ?
C27 C26 1.536(3) . ?
C27 C28 1.552(3) . ?
C42 C43 1.330(3) . ?
C40 C30 1.549(3) . ?
C2' C1' 1.504(3) . ?
C21 C30 1.548(3) . ?
C7' C9' 1.508(3) . ?
C7' C8' 1.503(4) . ?
C13 C15 1.518(3) . ?
C13 C14 1.335(3) . ?
C13 C12 1.465(3) . ?
C31 C32 1.471(3) . ?
C50 C43 1.511(3) . ?
C15 C16 1.530(3) . ?
C15 C17 1.522(3) . ?
C19 C4 1.539(3) . ?
C24 C38 1.544(3) . ?
C24 C39 1.543(3) . ?
C24 C25 1.554(3) . ?
C24 C23 1.536(3) . ?
C26 C25 1.513(3) . ?
C43 C44 1.514(3) . ?
C28 C34 1.506(3) . ?
C2 C3 1.526(3) . ?
C2 C1 1.531(3) . ?
C45 C46 1.494(3) . ?
C45 C44 1.541(3) . ?
C30 C25 1.568(3) . ?
C9 C10 1.545(3) . ?
C4' C5' 1.542(3) . ?
C4 C3 1.538(4) . ?
C4 C18 1.542(3) . ?
C4 C5 1.558(3) . ?
C47 C46 1.335(3) . ?
C47 C48 1.501(3) . ?
C47 C49 1.504(3) . ?
C32 C33 1.466(3) . ?
C10 C1 1.539(3) . ?
C10 C5 1.572(3) . ?
C10 C20 1.555(3) . ?
C35 C33 1.517(3) . ?
C35 C36 1.532(4) . ?
C35 C37 1.521(3) . ?
C34 C33 1.340(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
O1 C6 C7 119.0(2) . . ?
O1 C6 C5 125.0(2) . . ?
C5 C6 C7 116.01(18) . . ?
C23 C22 C21 110.83(17) . . ?
C3' C10' C7 111.71(18) . . ?
C31 C29 C28 118.73(18) . . ?
C31 C29 C30 121.40(18) . . ?
C28 C29 C30 119.75(17) . . ?
C42 C41 C28 114.32(18) . . ?
C7' C6' C5' 127.8(2) . . ?
O2 C11 C12 113.45(17) . . ?
C9 C11 O2 122.94(19) . . ?
C9 C11 C12 123.6(2) . . ?
C7 C8 C1' 111.98(16) . . ?
C9 C8 C1' 109.45(17) . . ?
C9 C8 C7 108.78(16) . . ?
C14 C8 C1' 103.61(16) . . ?
C14 C8 C7 108.89(17) . . ?
C14 C8 C9 114.12(17) . . ?
C10' C3' C4' 117.15(19) . . ?
C2' C3' C10' 121.42(19) . . ?
C2' C3' C4' 121.35(19) . . ?
C50 C27 C26 109.26(16) . . ?
C50 C27 C28 112.77(17) . . ?
C26 C27 C28 113.83(17) . . ?
C43 C42 C41 125.76(19) . . ?
C3' C2' C1' 125.89(19) . . ?
C22 C21 C30 113.55(18) . . ?
C6' C7' C9' 120.7(2) . . ?
C6' C7' C8' 125.3(2) . . ?
C8' C7' C9' 114.0(2) . . ?
C2' C1' C8 114.69(18) . . ?
C14 C13 C15 123.6(2) . . ?
C14 C13 C12 118.17(19) . . ?
C12 C13 C15 118.11(18) . . ?
O4 C31 C32 112.14(18) . . ?
C29 C31 O4 124.01(19) . . ?
C29 C31 C32 123.73(19) . . ?
C43 C50 C27 112.63(18) . . ?
C6 C7 C8 113.81(17) . . ?
C10' C7 C6 107.93(16) . . ?
C10' C7 C8 112.95(16) . . ?
C13 C15 C16 109.49(18) . . ?
C13 C15 C17 112.27(19) . . ?
C17 C15 C16 111.8(2) . . ?
C38 C24 C25 108.05(16) . . ?
C39 C24 C38 107.42(18) . . ?
C39 C24 C25 116.36(18) . . ?
C23 C24 C38 107.72(18) . . ?
C23 C24 C39 110.08(17) . . ?
C23 C24 C25 106.92(17) . . ?
O6 C26 C27 119.11(19) . . ?
O6 C26 C25 124.44(18) . . ?
C25 C26 C27 116.46(18) . . ?
C42 C43 C50 121.48(19) . . ?
C42 C43 C44 122.62(19) . . ?
C50 C43 C44 115.74(19) . . ?
C29 C28 C41 110.61(17) . . ?
C29 C28 C27 107.96(16) . . ?
C27 C28 C41 111.95(16) . . ?
C34 C28 C29 114.01(17) . . ?
C34 C28 C41 104.75(16) . . ?
C34 C28 C27 107.58(17) . . ?
C3 C2 C1 111.32(19) . . ?
C46 C45 C44 113.4(2) . . ?
C29 C30 C40 106.96(16) . . ?
C29 C30 C21 109.89(17) . . ?
C29 C30 C25 109.87(16) . . ?
C40 C30 C25 111.01(17) . . ?
C21 C30 C40 111.44(16) . . ?
C21 C30 C25 107.68(16) . . ?
C11 C9 C8 119.16(19) . . ?
C11 C9 C10 121.27(19) . . ?
C8 C9 C10 119.52(17) . . ?
C13 C14 C8 125.7(2) . . ?
C3' C4' C5' 111.27(18) . . ?
O3 C12 C11 118.51(19) . . ?
O3 C12 C13 123.14(19) . . ?
C13 C12 C11 118.29(18) . . ?
C19 C4 C18 107.60(19) . . ?
C19 C4 C5 115.72(19) . . ?
C3 C4 C19 109.9(2) . . ?
C3 C4 C18 107.7(2) . . ?
C3 C4 C5 107.79(18) . . ?
C18 C4 C5 107.85(18) . . ?
C2 C3 C4 113.6(2) . . ?
C46 C47 C48 121.0(2) . . ?
C46 C47 C49 124.8(2) . . ?
C48 C47 C49 114.2(2) . . ?
O5 C32 C31 117.71(19) . . ?
O5 C32 C33 123.1(2) . . ?
C33 C32 C31 119.07(18) . . ?
C9 C10 C5 109.81(17) . . ?
C9 C10 C20 106.34(16) . . ?
C1 C10 C9 110.49(17) . . ?
C1 C10 C5 108.09(17) . . ?
C1 C10 C20 111.36(18) . . ?
C20 C10 C5 110.75(17) . . ?
C33 C35 C36 109.7(2) . . ?
C33 C35 C37 113.72(19) . . ?
C37 C35 C36 110.2(2) . . ?
C2 C1 C10 113.17(18) . . ?
C47 C46 C45 127.3(2) . . ?
C33 C34 C28 126.13(19) . . ?
C6' C5' C4' 112.76(19) . . ?
C24 C25 C30 117.43(16) . . ?
C26 C25 C24 116.95(18) . . ?
C26 C25 C30 108.31(16) . . ?
C43 C44 C45 115.53(17) . . ?
C32 C33 C35 116.45(18) . . ?
C34 C33 C32 117.28(19) . . ?
C34 C33 C35 126.24(19) . . ?
C6 C5 C4 116.43(18) . . ?
C6 C5 C10 108.74(17) . . ?
C4 C5 C10 117.53(17) . . ?
C22 C23 C24 113.50(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
