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

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

data_20190488a
_database_code_depnum_ccdc_archive 'CCDC 1916739'
loop_
_audit_author_name
_audit_author_address
'Jing Zhou'
;Chongqing Medical University
China
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H50 O4'
_chemical_formula_sum            'C42 H50 O4'
_chemical_formula_weight         618.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.9497(5)
_cell_length_b                   13.0829(4)
_cell_length_c                   17.7686(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.929(3)
_cell_angle_gamma                90
_cell_volume                     3694.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6370
_cell_measurement_theta_min      3.5710
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.574
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    5.00   34.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -10.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   35.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   79.00  106.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00   85.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   49.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega   17.00   59.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega    3.00   82.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  9 omega   84.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   64.00   97.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   67.00   97.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   79.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   83.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   66.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   63.00  177.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 114

#__ type_ start__ end____ width___ exp.time_
 16 omega   85.00  178.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   99.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   68.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   89.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega   43.00   72.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0750900000
_diffrn_orient_matrix_UB_12      0.0674661000
_diffrn_orient_matrix_UB_13      0.0173975000
_diffrn_orient_matrix_UB_21      -0.0360424000
_diffrn_orient_matrix_UB_22      -0.0082965000
_diffrn_orient_matrix_UB_23      -0.0830259000
_diffrn_orient_matrix_UB_31      -0.0496109000
_diffrn_orient_matrix_UB_32      -0.0961425000
_diffrn_orient_matrix_UB_33      0.0194335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4903
_reflns_number_total             6598
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.030
_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)+(0.0735P)²+0.7628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1571
_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,H) groups, All O(H) groups
2.a Riding coordinates:
 O4(H4A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C30(H30), C34(H34)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.74979(11) 0.50384(14) 0.54804(10) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.72463(12) 0.40239(16) 0.54421(12) 0.0489(5) Uani 1 1 d . . . . .
H2 H 0.6983 0.3760 0.4996 0.059 Uiso 1 1 calc R . . . .
C3 C 0.73890(14) 0.34107(17) 0.60693(14) 0.0576(6) Uani 1 1 d . . . . .
H3 H 0.7219 0.2731 0.6046 0.069 Uiso 1 1 calc R . . . .
C4 C 0.77803(15) 0.37923(19) 0.67313(13) 0.0621(6) Uani 1 1 d . . . . .
H4 H 0.7876 0.3372 0.7152 0.075 Uiso 1 1 calc R . . . .
C5 C 0.80287(13) 0.47984(18) 0.67668(12) 0.0542(5) Uani 1 1 d . . . . .
H5 H 0.8294 0.5054 0.7214 0.065 Uiso 1 1 calc R . . . .
C6 C 0.78888(11) 0.54403(15) 0.61443(10) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.81584(11) 0.65390(15) 0.61799(10) 0.0429(4) Uani 1 1 d . . . . .
H7 H 0.8059 0.6805 0.6680 0.052 Uiso 1 1 calc R . . . .
C8 C 0.76352(11) 0.71890(15) 0.55801(10) 0.0413(4) Uani 1 1 d . . . . .
C9 C 0.77343(11) 0.66054(14) 0.48174(10) 0.0386(4) Uani 1 1 d . . . . .
C10 C 0.86667(11) 0.64272(14) 0.47390(10) 0.0409(4) Uani 1 1 d . . . . .
C11 C 0.92607(11) 0.64749(15) 0.53623(11) 0.0426(4) Uani 1 1 d . . . . .
C12 C 1.01139(12) 0.63834(18) 0.52780(13) 0.0542(5) Uani 1 1 d . . . . .
H12 H 1.0503 0.6449 0.5696 0.065 Uiso 1 1 calc R . . . .
C13 C 1.03839(14) 0.6198(2) 0.45834(14) 0.0631(6) Uani 1 1 d . . . . .
H13 H 1.0957 0.6153 0.4527 0.076 Uiso 1 1 calc R . . . .
C14 C 0.98039(15) 0.6077(2) 0.39602(13) 0.0642(6) Uani 1 1 d . . . . .
H14 H 0.9985 0.5918 0.3490 0.077 Uiso 1 1 calc R . . . .
C15 C 0.89619(13) 0.61939(17) 0.40430(11) 0.0529(5) Uani 1 1 d . . . . .
H15 H 0.8577 0.6115 0.3623 0.064 Uiso 1 1 calc R . . . .
C16 C 0.67402(12) 0.72055(16) 0.57615(11) 0.0451(4) Uani 1 1 d . . . . .
H16 H 0.6451 0.6588 0.5734 0.054 Uiso 1 1 calc R . . . .
C17 C 0.63203(12) 0.80257(16) 0.59587(11) 0.0464(5) Uani 1 1 d . . . . .
C18 C 0.67642(13) 0.90297(17) 0.60042(12) 0.0531(5) Uani 1 1 d . . . . .
C19 C 0.76330(13) 0.90930(15) 0.57557(11) 0.0473(5) Uani 1 1 d . . . . .
C20 C 0.80069(12) 0.82342(15) 0.55597(11) 0.0461(5) Uani 1 1 d . . . . .
H20 H 0.8544 0.8291 0.5397 0.055 Uiso 1 1 calc R . . . .
C21 C 0.53901(13) 0.7980(2) 0.61249(12) 0.0578(6) Uani 1 1 d . . . . .
C22 C 0.50445(16) 0.6897(3) 0.6028(2) 0.0940(10) Uani 1 1 d . . . . .
H22A H 0.5109 0.6664 0.5524 0.141 Uiso 1 1 calc GR . . . .
H22B H 0.4459 0.6894 0.6116 0.141 Uiso 1 1 calc GR . . . .
H22C H 0.5348 0.6452 0.6384 0.141 Uiso 1 1 calc GR . . . .
C23 C 0.52806(17) 0.8307(3) 0.69398(15) 0.0881(9) Uani 1 1 d . . . . .
H23A H 0.5602 0.7862 0.7283 0.132 Uiso 1 1 calc GR . . . .
H23B H 0.4697 0.8267 0.7030 0.132 Uiso 1 1 calc GR . . . .
H23C H 0.5475 0.8997 0.7016 0.132 Uiso 1 1 calc GR . . . .
C24 C 0.48735(17) 0.8687(3) 0.55789(18) 0.1021(11) Uani 1 1 d . . . . .
H24A H 0.5047 0.9382 0.5670 0.153 Uiso 1 1 calc GR . . . .
H24B H 0.4287 0.8620 0.5655 0.153 Uiso 1 1 calc GR . . . .
H24C H 0.4961 0.8503 0.5069 0.153 Uiso 1 1 calc GR . . . .
C25 C 0.80545(15) 1.01415(17) 0.57161(14) 0.0590(6) Uani 1 1 d . . . . .
C26 C 0.81585(19) 1.0649(2) 0.64995(16) 0.0802(8) Uani 1 1 d . . . . .
H26A H 0.7614 1.0772 0.6673 0.120 Uiso 1 1 calc GR . . . .
H26B H 0.8451 1.1287 0.6465 0.120 Uiso 1 1 calc GR . . . .
H26C H 0.8475 1.0206 0.6848 0.120 Uiso 1 1 calc GR . . . .
C27 C 0.7515(2) 1.0824(2) 0.51570(16) 0.0817(8) Uani 1 1 d . . . . .
H27A H 0.7420 1.0479 0.4680 0.123 Uiso 1 1 calc GR . . . .
H27B H 0.7805 1.1456 0.5088 0.123 Uiso 1 1 calc GR . . . .
H27C H 0.6985 1.0962 0.5355 0.123 Uiso 1 1 calc GR . . . .
C28 C 0.89377(18) 1.0052(2) 0.5436(2) 0.0913(9) Uani 1 1 d . . . . .
H28A H 0.9284 0.9628 0.5776 0.137 Uiso 1 1 calc GR . . . .
H28B H 0.9185 1.0720 0.5416 0.137 Uiso 1 1 calc GR . . . .
H28C H 0.8895 0.9753 0.4940 0.137 Uiso 1 1 calc GR . . . .
C29 C 0.72713(11) 0.71544(15) 0.41451(10) 0.0418(4) Uani 1 1 d . . . . .
C30 C 0.64438(11) 0.69147(15) 0.39213(11) 0.0444(4) Uani 1 1 d . . . . .
H30 H 0.6180 0.6405 0.4180 0.053 Uiso 1 1 calc R . . . .
C31 C 0.59893(12) 0.74088(17) 0.33221(11) 0.0499(5) Uani 1 1 d . . . . .
C32 C 0.64036(14) 0.81693(18) 0.29499(12) 0.0569(6) Uani 1 1 d . . . . .
C33 C 0.72517(15) 0.84132(18) 0.31356(13) 0.0584(6) Uani 1 1 d . . . . .
C34 C 0.76609(13) 0.79004(17) 0.37495(12) 0.0522(5) Uani 1 1 d . . . . .
H34 H 0.8217 0.8067 0.3898 0.063 Uiso 1 1 calc R . . . .
C35 C 0.50700(13) 0.70962(19) 0.30811(13) 0.0578(6) Uani 1 1 d . . . . .
C36 C 0.47838(15) 0.6207(2) 0.35581(16) 0.0790(8) Uani 1 1 d . . . . .
H36A H 0.5149 0.5632 0.3510 0.118 Uiso 1 1 calc GR . . . .
H36B H 0.4218 0.6020 0.3385 0.118 Uiso 1 1 calc GR . . . .
H36C H 0.4805 0.6412 0.4078 0.118 Uiso 1 1 calc GR . . . .
C37 C 0.44673(15) 0.8000(2) 0.31756(16) 0.0760(7) Uani 1 1 d . . . . .
H37A H 0.4514 0.8216 0.3694 0.114 Uiso 1 1 calc GR . . . .
H37B H 0.3900 0.7789 0.3032 0.114 Uiso 1 1 calc GR . . . .
H37C H 0.4613 0.8556 0.2860 0.114 Uiso 1 1 calc GR . . . .
C38 C 0.49845(18) 0.6718(2) 0.22550(15) 0.0802(8) Uani 1 1 d . . . . .
H38A H 0.5163 0.7247 0.1930 0.120 Uiso 1 1 calc GR . . . .
H38B H 0.4408 0.6548 0.2110 0.120 Uiso 1 1 calc GR . . . .
H38C H 0.5330 0.6123 0.2211 0.120 Uiso 1 1 calc GR . . . .
C39 C 0.77255(18) 0.9183(2) 0.26713(15) 0.0794(8) Uani 1 1 d . . . . .
C40 C 0.7368(3) 1.0271(2) 0.27706(18) 0.1105(12) Uani 1 1 d . . . . .
H40A H 0.6769 1.0261 0.2654 0.166 Uiso 1 1 calc GR . . . .
H40B H 0.7618 1.0734 0.2436 0.166 Uiso 1 1 calc GR . . . .
H40C H 0.7495 1.0490 0.3283 0.166 Uiso 1 1 calc GR . . . .
C41 C 0.7666(2) 0.8890(3) 0.18347(16) 0.0998(11) Uani 1 1 d . . . . .
H41A H 0.7888 0.8214 0.1782 0.150 Uiso 1 1 calc GR . . . .
H41B H 0.7984 0.9367 0.1564 0.150 Uiso 1 1 calc GR . . . .
H41C H 0.7087 0.8905 0.1634 0.150 Uiso 1 1 calc GR . . . .
C42 C 0.8671(2) 0.9199(3) 0.2938(2) 0.1189(14) Uani 1 1 d . . . . .
H42A H 0.8750 0.9509 0.3429 0.178 Uiso 1 1 calc GR . . . .
H42B H 0.8970 0.9586 0.2588 0.178 Uiso 1 1 calc GR . . . .
H42C H 0.8883 0.8512 0.2965 0.178 Uiso 1 1 calc GR . . . .
O1 O 0.73175(8) 0.56179(10) 0.48466(7) 0.0419(3) Uani 1 1 d . . . . .
O2 O 0.90449(8) 0.66373(11) 0.60854(7) 0.0466(3) Uani 1 1 d . . . . .
O3 O 0.64308(12) 0.97862(14) 0.62520(12) 0.0879(6) Uani 1 1 d . . . . .
O4 O 0.59931(11) 0.87097(15) 0.23614(9) 0.0801(6) Uani 1 1 d . . . . .
H4A H 0.5526 0.8865 0.2012 0.120 Uiso 1 1 d R . . . .


_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
C1 C2 1.387(3) . ?
C1 C6 1.389(3) . ?
C1 O1 1.368(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.500(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.550(3) . ?
C7 O2 1.444(2) . ?
C8 C9 1.575(3) . ?
C8 C16 1.490(2) . ?
C8 C20 1.492(3) . ?
C9 C10 1.523(2) . ?
C9 C29 1.529(2) . ?
C9 O1 1.456(2) . ?
C10 C11 1.396(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.387(3) . ?
C11 O2 1.375(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.328(3) . ?
C17 C18 1.491(3) . ?
C17 C21 1.538(3) . ?
C18 C19 1.492(3) . ?
C18 O3 1.223(3) . ?
C19 C20 1.332(3) . ?
C19 C25 1.532(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.525(4) . ?
C21 C23 1.534(3) . ?
C21 C24 1.529(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.538(3) . ?
C25 C27 1.542(3) . ?
C25 C28 1.539(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.381(3) . ?
C29 C34 1.381(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.394(3) . ?
C31 C32 1.392(3) . ?
C31 C35 1.547(3) . ?
C32 C33 1.401(3) . ?
C32 O4 1.380(2) . ?
C33 C34 1.394(3) . ?
C33 C39 1.541(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.532(4) . ?
C35 C37 1.542(3) . ?
C35 C38 1.544(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.548(4) . ?
C39 C41 1.530(4) . ?
C39 C42 1.542(4) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
O4 H4A 0.9498 . ?

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
C2 C1 C6 120.72(18) . . ?
O1 C1 C2 116.79(17) . . ?
O1 C1 C6 122.46(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.43(19) . . ?
C1 C6 C7 120.30(16) . . ?
C5 C6 C7 121.27(18) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 111.18(15) . . ?
C8 C7 H7 108.1 . . ?
O2 C7 C6 111.13(15) . . ?
O2 C7 H7 108.1 . . ?
O2 C7 C8 110.24(15) . . ?
C7 C8 C9 103.75(14) . . ?
C16 C8 C7 109.17(15) . . ?
C16 C8 C9 111.21(15) . . ?
C16 C8 C20 112.45(16) . . ?
C20 C8 C7 109.14(15) . . ?
C20 C8 C9 110.72(15) . . ?
C10 C9 C8 108.89(14) . . ?
C10 C9 C29 114.23(15) . . ?
C29 C9 C8 111.54(15) . . ?
O1 C9 C8 108.63(14) . . ?
O1 C9 C10 108.65(14) . . ?
O1 C9 C29 104.68(14) . . ?
C11 C10 C9 121.48(16) . . ?
C15 C10 C9 121.42(16) . . ?
C15 C10 C11 117.10(17) . . ?
C12 C11 C10 121.07(18) . . ?
O2 C11 C10 122.76(16) . . ?
O2 C11 C12 116.16(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.15(19) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 H15 119.1 . . ?
C8 C16 H16 117.2 . . ?
C17 C16 C8 125.66(19) . . ?
C17 C16 H16 117.2 . . ?
C16 C17 C18 118.57(18) . . ?
C16 C17 C21 122.4(2) . . ?
C18 C17 C21 119.00(18) . . ?
C17 C18 C19 118.79(17) . . ?
O3 C18 C17 120.9(2) . . ?
O3 C18 C19 120.3(2) . . ?
C18 C19 C25 119.05(18) . . ?
C20 C19 C18 118.57(19) . . ?
C20 C19 C25 122.35(19) . . ?
C8 C20 H20 117.3 . . ?
C19 C20 C8 125.37(18) . . ?
C19 C20 H20 117.3 . . ?
C22 C21 C17 111.07(18) . . ?
C22 C21 C23 107.2(2) . . ?
C22 C21 C24 108.7(2) . . ?
C23 C21 C17 111.11(18) . . ?
C24 C21 C17 109.3(2) . . ?
C24 C21 C23 109.4(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 C26 111.0(2) . . ?
C19 C25 C27 109.00(19) . . ?
C19 C25 C28 111.37(18) . . ?
C26 C25 C27 110.1(2) . . ?
C26 C25 C28 107.2(2) . . ?
C28 C25 C27 108.1(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C9 120.25(17) . . ?
C34 C29 C9 121.43(16) . . ?
C34 C29 C30 118.31(17) . . ?
C29 C30 H30 118.8 . . ?
C29 C30 C31 122.40(18) . . ?
C31 C30 H30 118.8 . . ?
C30 C31 C35 120.47(19) . . ?
C32 C31 C30 117.19(18) . . ?
C32 C31 C35 122.33(18) . . ?
C31 C32 C33 122.60(18) . . ?
O4 C32 C31 120.8(2) . . ?
O4 C32 C33 116.6(2) . . ?
C32 C33 C39 122.1(2) . . ?
C34 C33 C32 116.88(19) . . ?
C34 C33 C39 121.0(2) . . ?
C29 C34 C33 122.51(19) . . ?
C29 C34 H34 118.7 . . ?
C33 C34 H34 118.7 . . ?
C36 C35 C31 111.59(17) . . ?
C36 C35 C37 107.7(2) . . ?
C36 C35 C38 106.0(2) . . ?
C37 C35 C31 110.6(2) . . ?
C37 C35 C38 110.15(19) . . ?
C38 C35 C31 110.6(2) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33 C39 C40 109.7(2) . . ?
C33 C39 C42 110.9(2) . . ?
C41 C39 C33 111.3(2) . . ?
C41 C39 C40 110.4(2) . . ?
C41 C39 C42 106.3(3) . . ?
C42 C39 C40 108.2(3) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C1 O1 C9 117.19(13) . . ?
C11 O2 C7 114.90(13) . . ?
C32 O4 H4A 154.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O2 0.95 2.84 3.714(2) 153.7 4_575

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 24.2(2) . . . . ?
C1 C6 C7 O2 -98.98(19) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -179.99(17) . . . . ?
C2 C1 O1 C9 -166.73(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 179.99(19) . . . . ?
C5 C6 C7 C8 -156.38(17) . . . . ?
C5 C6 C7 O2 80.4(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C1 O1 C9 15.4(2) . . . . ?
C6 C7 C8 C9 -53.64(18) . . . . ?
C6 C7 C8 C16 65.0(2) . . . . ?
C6 C7 C8 C20 -171.71(15) . . . . ?
C6 C7 O2 C11 73.14(19) . . . . ?
C7 C8 C9 C10 -51.65(18) . . . . ?
C7 C8 C9 C29 -178.61(14) . . . . ?
C7 C8 C9 O1 66.51(16) . . . . ?
C7 C8 C16 C17 115.0(2) . . . . ?
C7 C8 C20 C19 -114.5(2) . . . . ?
C8 C7 O2 C11 -50.6(2) . . . . ?
C8 C9 C10 C11 19.2(2) . . . . ?
C8 C9 C10 C15 -161.76(18) . . . . ?
C8 C9 C29 C30 -90.6(2) . . . . ?
C8 C9 C29 C34 89.0(2) . . . . ?
C8 C9 O1 C1 -48.70(19) . . . . ?
C8 C16 C17 C18 0.3(3) . . . . ?
C8 C16 C17 C21 178.99(18) . . . . ?
C9 C8 C16 C17 -131.1(2) . . . . ?
C9 C8 C20 C19 131.9(2) . . . . ?
C9 C10 C11 C12 -175.40(18) . . . . ?
C9 C10 C11 O2 3.0(3) . . . . ?
C9 C10 C15 C14 177.0(2) . . . . ?
C9 C29 C30 C31 178.62(18) . . . . ?
C9 C29 C34 C33 -179.9(2) . . . . ?
C10 C9 C29 C30 145.38(18) . . . . ?
C10 C9 C29 C34 -35.0(3) . . . . ?
C10 C9 O1 C1 69.61(18) . . . . ?
C10 C11 C12 C13 -3.0(3) . . . . ?
C10 C11 O2 C7 12.6(3) . . . . ?
C11 C10 C15 C14 -3.9(3) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C11 O2 C7 -168.92(17) . . . . ?
C12 C13 C14 C15 3.1(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C15 C10 C11 C12 5.6(3) . . . . ?
C15 C10 C11 O2 -176.03(18) . . . . ?
C16 C8 C9 C10 -168.89(15) . . . . ?
C16 C8 C9 C29 64.1(2) . . . . ?
C16 C8 C9 O1 -50.72(19) . . . . ?
C16 C8 C20 C19 6.8(3) . . . . ?
C16 C17 C18 C19 5.8(3) . . . . ?
C16 C17 C18 O3 -173.0(2) . . . . ?
C16 C17 C21 C22 -0.2(3) . . . . ?
C16 C17 C21 C23 119.0(3) . . . . ?
C16 C17 C21 C24 -120.2(3) . . . . ?
C17 C18 C19 C20 -5.3(3) . . . . ?
C17 C18 C19 C25 173.17(18) . . . . ?
C18 C17 C21 C22 178.5(2) . . . . ?
C18 C17 C21 C23 -62.3(3) . . . . ?
C18 C17 C21 C24 58.5(3) . . . . ?
C18 C19 C20 C8 -1.3(3) . . . . ?
C18 C19 C25 C26 61.7(3) . . . . ?
C18 C19 C25 C27 -59.8(3) . . . . ?
C18 C19 C25 C28 -179.0(2) . . . . ?
C20 C8 C9 C10 65.32(19) . . . . ?
C20 C8 C9 C29 -61.64(19) . . . . ?
C20 C8 C9 O1 -176.52(14) . . . . ?
C20 C8 C16 C17 -6.3(3) . . . . ?
C20 C19 C25 C26 -119.9(2) . . . . ?
C20 C19 C25 C27 118.7(2) . . . . ?
C20 C19 C25 C28 -0.5(3) . . . . ?
C21 C17 C18 C19 -172.91(18) . . . . ?
C21 C17 C18 O3 8.3(3) . . . . ?
C25 C19 C20 C8 -179.72(19) . . . . ?
C29 C9 C10 C11 144.65(18) . . . . ?
C29 C9 C10 C15 -36.4(3) . . . . ?
C29 C9 O1 C1 -167.97(14) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C29 C30 C31 C35 178.6(2) . . . . ?
C30 C29 C34 C33 -0.2(3) . . . . ?
C30 C31 C32 C33 2.7(3) . . . . ?
C30 C31 C32 O4 -178.6(2) . . . . ?
C30 C31 C35 C36 -1.6(3) . . . . ?
C30 C31 C35 C37 118.2(2) . . . . ?
C30 C31 C35 C38 -119.4(2) . . . . ?
C31 C32 C33 C34 -3.9(4) . . . . ?
C31 C32 C33 C39 174.1(2) . . . . ?
C32 C31 C35 C36 177.1(2) . . . . ?
C32 C31 C35 C37 -63.0(3) . . . . ?
C32 C31 C35 C38 59.3(3) . . . . ?
C32 C33 C34 C29 2.6(4) . . . . ?
C32 C33 C39 C40 67.9(3) . . . . ?
C32 C33 C39 C41 -54.6(4) . . . . ?
C32 C33 C39 C42 -172.7(3) . . . . ?
C34 C29 C30 C31 -1.1(3) . . . . ?
C34 C33 C39 C40 -114.3(3) . . . . ?
C34 C33 C39 C41 123.3(3) . . . . ?
C34 C33 C39 C42 5.2(4) . . . . ?
C35 C31 C32 C33 -176.0(2) . . . . ?
C35 C31 C32 O4 2.6(3) . . . . ?
C39 C33 C34 C29 -175.4(2) . . . . ?
O1 C1 C2 C3 -178.15(17) . . . . ?
O1 C1 C6 C5 178.44(17) . . . . ?
O1 C1 C6 C7 -2.1(3) . . . . ?
O1 C9 C10 C11 -98.9(2) . . . . ?
O1 C9 C10 C15 80.1(2) . . . . ?
O1 C9 C29 C30 26.7(2) . . . . ?
O1 C9 C29 C34 -153.66(18) . . . . ?
O2 C7 C8 C9 70.06(17) . . . . ?
O2 C7 C8 C16 -171.29(15) . . . . ?
O2 C7 C8 C20 -48.01(19) . . . . ?
O2 C11 C12 C13 178.5(2) . . . . ?
O3 C18 C19 C20 173.4(2) . . . . ?
O3 C18 C19 C25 -8.0(3) . . . . ?
O4 C32 C33 C34 177.4(2) . . . . ?
O4 C32 C33 C39 -4.6(4) . . . . ?

_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_201910273
_database_code_depnum_ccdc_archive 'CCDC 2167147'
loop_
_audit_author_name
_audit_author_address
b
;Chongqing Medical University
China
;
_audit_update_record             
;
2022-04-18 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H40 O2'
_chemical_formula_sum            'C28 H40 O2'
_chemical_formula_weight         408.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4Cl4
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1016(6)
_cell_length_b                   10.4244(9)
_cell_length_c                   10.5390(8)
_cell_angle_alpha                81.508(7)
_cell_angle_beta                 75.932(8)
_cell_angle_gamma                81.583(8)
_cell_volume                     638.83(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4690
_cell_measurement_theta_min      4.2860
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4594
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.317
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    1.50    --  -33.50  57.00  90.00   87
  2  ω   -102.00 -15.00   1.00    1.50    --  -33.50 -57.00 -60.00   87
  3  ω   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 150.00   93
  4  ω      3.00  81.00   1.00    1.50    --   36.47-106.00 -78.00   78
  5  ω     -4.00  77.00   1.00    1.50    --   36.47 -99.00  60.00   81
  6  ω     57.00 110.00   1.00    1.50    --   36.47 178.00-120.00   53
  7  ω    -34.00  59.00   1.00    1.50    --   36.47 -37.00 -60.00   93
  8  ω    -32.00  55.00   1.00    1.50    --   36.47 -57.00-150.00   87
  9  ω     57.00 110.00   1.00    1.50    --   36.47 178.00 -60.00   53
 10  ω      8.00 106.00   1.00    1.50    --   36.47  77.00  90.00   98
 11  ω     37.00 134.00   1.00    5.00    --  108.00 -30.00 -60.00   97
 12  ω     38.00 110.00   1.00    5.00    --  108.00 -94.00   0.00   72
 13  ω     38.00 110.00   1.00    5.00    --  108.00 -94.00  90.00   72
 14  ω     79.00 177.00   1.00    5.00    --  108.00  77.00-120.00   98
 15  ω     50.00 134.00   1.00    5.00    --  108.00 -30.00  60.00   84
 16  ω     77.00 110.00   1.00    5.00    --  108.00 -61.00  90.00   33
 17  ω     47.00  73.00   1.00    5.00    --  108.00 -61.00  90.00   26
 18  ω    101.00 127.00   1.00    5.00    --  108.00 -77.00 -60.00   26
 19  ω     76.00 108.00   1.00    5.00    --  108.00-111.00 -60.00   32
 20  ω     40.00 124.00   1.00    5.00    --  108.00 -61.00-180.00   84
 21  ω     46.00  72.00   1.00    5.00    --  108.00-111.00 -60.00   26
 22  ω     37.00 136.00   1.00    5.00    --  108.00 -15.00 150.00   99
 23  ω     42.00  80.00   1.00    5.00    --  108.00 -77.00 -60.00   38
 24  ω     75.00 105.00   1.00    5.00    --  108.00-111.00-150.00   30
 25  ω     42.00 124.00   1.00    5.00    --  108.00 -15.00-120.00   82
;
_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      -0.1618771000
_diffrn_orient_matrix_UB_12      0.1232028000
_diffrn_orient_matrix_UB_13      0.0379561000
_diffrn_orient_matrix_UB_21      -0.2058009000
_diffrn_orient_matrix_UB_22      -0.0725330000
_diffrn_orient_matrix_UB_23      0.0065998000
_diffrn_orient_matrix_UB_31      -0.0102025000
_diffrn_orient_matrix_UB_32      -0.0467678000
_diffrn_orient_matrix_UB_33      0.1467635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1616
_reflns_number_total             2279
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0527
_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)+(0.0757P)²+0.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1576
_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,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0466(3) 0.64565(18) 0.58129(15) 0.0829(7) Uani 1 1 d . . . . .
C1 C 0.1571(3) 0.73781(19) 0.55917(18) 0.0481(5) Uani 1 1 d . . . . .
C2 C 0.1564(3) 0.81676(17) 0.66653(17) 0.0398(4) Uani 1 1 d . . . . .
C3 C 0.2872(3) 0.91495(17) 0.63928(17) 0.0405(4) Uani 1 1 d . . . . .
H3 H 0.2846 0.9638 0.7068 0.049 Uiso 1 1 calc R . . . .
C4 C 0.4320(3) 0.94930(17) 0.51129(17) 0.0389(4) Uani 1 1 d . . . . .
C5 C 0.4265(3) 0.87259(18) 0.40835(17) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.5175 0.8925 0.3251 0.049 Uiso 1 1 calc R . . . .
C6 C 0.2976(3) 0.77434(17) 0.42604(17) 0.0399(4) Uani 1 1 d . . . . .
C7 C 0.0054(3) 0.78319(19) 0.80327(17) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.0234(4) 0.8746(2) 0.9001(2) 0.0635(6) Uani 1 1 d . . . . .
H8A H 0.1772 0.8654 0.9105 0.095 Uiso 1 1 calc GR . . . .
H8B H -0.0764 0.8527 0.9838 0.095 Uiso 1 1 calc GR . . . .
H8C H -0.0192 0.9632 0.8669 0.095 Uiso 1 1 calc GR . . . .
C9 C 0.0781(5) 0.6434(2) 0.8603(2) 0.0733(7) Uani 1 1 d . . . . .
H9A H 0.0643 0.5830 0.8029 0.110 Uiso 1 1 calc GR . . . .
H9B H -0.0179 0.6237 0.9458 0.110 Uiso 1 1 calc GR . . . .
H9C H 0.2333 0.6362 0.8676 0.110 Uiso 1 1 calc GR . . . .
C10 C -0.2449(4) 0.7972(3) 0.7940(2) 0.0690(7) Uani 1 1 d . . . . .
H10A H -0.2904 0.8857 0.7617 0.104 Uiso 1 1 calc GR . . . .
H10B H -0.3387 0.7751 0.8797 0.104 Uiso 1 1 calc GR . . . .
H10C H -0.2618 0.7395 0.7348 0.104 Uiso 1 1 calc GR . . . .
C11 C 0.2927(3) 0.69663(18) 0.31377(18) 0.0443(5) Uani 1 1 d . . . . .
C12 C 0.3803(4) 0.5524(2) 0.3452(2) 0.0618(6) Uani 1 1 d . . . . .
H12A H 0.5314 0.5460 0.3591 0.093 Uiso 1 1 calc GR . . . .
H12B H 0.3822 0.5058 0.2728 0.093 Uiso 1 1 calc GR . . . .
H12C H 0.2818 0.5154 0.4233 0.093 Uiso 1 1 calc GR . . . .
C13 C 0.0486(4) 0.7074(2) 0.2949(2) 0.0636(6) Uani 1 1 d . . . . .
H13A H -0.0470 0.6689 0.3734 0.095 Uiso 1 1 calc GR . . . .
H13B H 0.0476 0.6623 0.2220 0.095 Uiso 1 1 calc GR . . . .
H13C H -0.0073 0.7977 0.2776 0.095 Uiso 1 1 calc GR . . . .
C14 C 0.4426(4) 0.7489(2) 0.18308(19) 0.0620(6) Uani 1 1 d . . . . .
H14A H 0.3915 0.8392 0.1612 0.093 Uiso 1 1 calc GR . . . .
H14B H 0.4327 0.6998 0.1148 0.093 Uiso 1 1 calc GR . . . .
H14C H 0.5975 0.7405 0.1912 0.093 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(2) . ?
C1 C2 1.493(2) . ?
C1 C6 1.484(2) . ?
C2 C3 1.345(2) . ?
C2 C7 1.532(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.449(2) . ?
C4 C4 1.396(3) 2_676 ?
C4 C5 1.449(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.345(2) . ?
C6 C11 1.538(2) . ?
C7 C8 1.528(3) . ?
C7 C9 1.537(3) . ?
C7 C10 1.538(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.536(3) . ?
C11 C13 1.536(3) . ?
C11 C14 1.530(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O1 C1 C2 120.54(17) . . ?
O1 C1 C6 121.33(18) . . ?
C6 C1 C2 118.13(15) . . ?
C1 C2 C7 118.67(15) . . ?
C3 C2 C1 118.74(16) . . ?
C3 C2 C7 122.59(16) . . ?
C2 C3 H3 118.0 . . ?
C2 C3 C4 124.04(16) . . ?
C4 C3 H3 118.0 . . ?
C3 C4 C5 116.07(15) . . ?
C4 C4 C3 121.8(2) 2_676 . ?
C4 C4 C5 122.12(19) 2_676 . ?
C4 C5 H5 118.0 . . ?
C6 C5 C4 123.93(16) . . ?
C6 C5 H5 118.0 . . ?
C1 C6 C11 118.47(15) . . ?
C5 C6 C1 119.01(16) . . ?
C5 C6 C11 122.51(16) . . ?
C2 C7 C9 110.39(17) . . ?
C2 C7 C10 109.74(16) . . ?
C8 C7 C2 111.60(15) . . ?
C8 C7 C9 107.29(18) . . ?
C8 C7 C10 107.65(19) . . ?
C9 C7 C10 110.11(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C6 110.32(16) . . ?
C12 C11 C13 109.56(17) . . ?
C13 C11 C6 109.78(17) . . ?
C14 C11 C6 111.60(15) . . ?
C14 C11 C12 107.80(18) . . ?
C14 C11 C13 107.71(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.6(2) . . . . ?
O1 C1 C2 C7 -2.8(3) . . . . ?
O1 C1 C6 C5 -176.4(2) . . . . ?
O1 C1 C6 C11 2.7(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C7 C8 -179.27(19) . . . . ?
C1 C2 C7 C9 61.5(2) . . . . ?
C1 C2 C7 C10 -60.0(2) . . . . ?
C1 C6 C11 C12 -61.4(2) . . . . ?
C1 C6 C11 C13 59.4(2) . . . . ?
C1 C6 C11 C14 178.75(19) . . . . ?
C2 C1 C6 C5 3.0(3) . . . . ?
C2 C1 C6 C11 -177.87(17) . . . . ?
C2 C3 C4 C4 -178.8(2) . . . 2_676 ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C2 C7 C8 0.4(3) . . . . ?
C3 C2 C7 C9 -118.9(2) . . . . ?
C3 C2 C7 C10 119.6(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C4 C5 C6 -179.9(2) 2_676 . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C5 C6 C11 178.83(18) . . . . ?
C5 C6 C11 C12 117.6(2) . . . . ?
C5 C6 C11 C13 -121.5(2) . . . . ?
C5 C6 C11 C14 -2.2(3) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C1 C2 C7 177.84(17) . . . . ?
C7 C2 C3 C4 179.95(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.859
