# 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_201907173a
_database_code_depnum_ccdc_archive 'CCDC 1991270'
loop_
_audit_author_name
_audit_author_address
'Xiang Min'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences,
China
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;
_audit_creation_date             2019-07-04
_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         'C33 H37 N O5'
_chemical_formula_sum            'C33 H37 N O5'
_chemical_formula_weight         527.63
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.2748(4)
_cell_length_b                   14.2248(3)
_cell_length_c                   10.9525(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.500(4)
_cell_angle_gamma                90
_cell_volume                     1444.85(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7700
_cell_measurement_theta_min      4.4850
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81666
_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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10407
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.473
_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  -52.00   35.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000    0.0000 174

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   -4.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -20.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 162

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  101.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   74.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega   71.00  108.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00   46.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   58.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   18.00   82.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 128

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00   62.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega   61.00  100.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 13 omega  -27.00   18.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 14 omega  -27.00   13.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   60.0000 80

#__ type_ start__ end____ width___ exp.time_
 15 omega   57.00  107.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 16 omega   59.00  109.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  109.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   96.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 114

#__ type_ start__ end____ width___ exp.time_
 19 omega   88.00  177.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 178

#__ type_ start__ end____ width___ exp.time_
 20 omega   63.00  141.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 156

#__ type_ start__ end____ width___ exp.time_
 21 omega  146.00  178.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 22 omega   66.00   97.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 62

#__ type_ start__ end____ width___ exp.time_
 23 omega   67.00   99.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 24 omega   56.00   90.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
 25 omega  142.00  171.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 26 omega   89.00  169.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 160

#__ type_ start__ end____ width___ exp.time_
 27 omega   86.00  111.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 28 omega   38.00   99.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 122

#__ type_ start__ end____ width___ exp.time_
 29 omega   85.00  111.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 30 omega   56.00  120.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 128

#__ type_ start__ end____ width___ exp.time_
 31 omega   99.00  126.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 32 omega   82.00  167.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 170

#__ type_ start__ end____ width___ exp.time_
 33 omega   82.00  136.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 108

#__ type_ start__ end____ width___ exp.time_
 34 omega  133.00  176.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0117010000
_diffrn_orient_matrix_UB_12      -0.0962327000
_diffrn_orient_matrix_UB_13      0.0685028000
_diffrn_orient_matrix_UB_21      0.1625236000
_diffrn_orient_matrix_UB_22      0.0163564000
_diffrn_orient_matrix_UB_23      0.0858789000
_diffrn_orient_matrix_UB_31      -0.0326358000
_diffrn_orient_matrix_UB_32      0.0469324000
_diffrn_orient_matrix_UB_33      0.1104710000
_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         0.914
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4645
_reflns_number_total             5148
_reflns_odcompleteness_completeness 99.96
_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         0.222
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.106
_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)+(0.0663P)²+0.0215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1214
_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. Rigid bond restraints
 C2, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C9, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Riding coordinates:
 O5(H5)
4.b Ternary CH refined with riding coordinates:
 C7(H7)
4.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
4.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C19(H19), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33)
4.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.5836(4) 0.2478(2) 0.6215(3) 0.0563(9) Uani 1 1 d . . . . .
C2 C 0.4922(4) 0.2598(2) 0.4679(3) 0.0490(6) Uani 1 1 d . U . . .
C3 C 0.5046(3) 0.3656(2) 0.4418(3) 0.0429(6) Uani 1 1 d . . . . .
C4 C 0.5485(3) 0.4081(2) 0.5837(3) 0.0444(6) Uani 1 1 d . . . . .
C5 C 0.6285(4) 0.3833(3) 0.4006(4) 0.0590(9) Uani 1 1 d . . . . .
H5A H 0.7156 0.3545 0.4675 0.071 Uiso 1 1 calc R . . . .
H5B H 0.6053 0.3522 0.3148 0.071 Uiso 1 1 calc R . . . .
C6 C 0.6590(5) 0.4864(4) 0.3870(5) 0.0819(13) Uani 1 1 d . . . . .
H6A H 0.5732 0.5159 0.3218 0.123 Uiso 1 1 calc GR . . . .
H6B H 0.7343 0.4913 0.3577 0.123 Uiso 1 1 calc GR . . . .
H6C H 0.6887 0.5170 0.4729 0.123 Uiso 1 1 calc GR . . . .
C7 C 0.3617(4) 0.4131(2) 0.3448(3) 0.0463(7) Uani 1 1 d . . . . .
H7 H 0.3758 0.4812 0.3574 0.056 Uiso 1 1 calc R . . . .
C8 C 0.2504(4) 0.3859(3) 0.3925(3) 0.0551(8) Uani 1 1 d . U . . .
C9 C 0.2511(4) 0.2958(3) 0.4401(3) 0.0610(8) Uani 1 1 d . U . . .
C10 C 0.1484(5) 0.2648(5) 0.4824(4) 0.0918(17) Uani 1 1 d . U . . .
H10 H 0.1493 0.2038 0.5132 0.110 Uiso 1 1 calc R . . . .
C11 C 0.0438(6) 0.3302(8) 0.4762(5) 0.116(3) Uani 1 1 d . U . . .
H11 H -0.0288 0.3111 0.5000 0.140 Uiso 1 1 calc R . . . .
C12 C 0.0449(6) 0.4207(7) 0.4365(5) 0.114(3) Uani 1 1 d . U . . .
H12 H -0.0223 0.4636 0.4387 0.137 Uiso 1 1 calc R . . . .
C13 C 0.1469(5) 0.4485(4) 0.3930(4) 0.0855(16) Uani 1 1 d . U . . .
H13 H 0.1462 0.5099 0.3636 0.103 Uiso 1 1 calc R . . . .
C14 C 0.3116(3) 0.3932(2) 0.1937(3) 0.0441(7) Uani 1 1 d . . . . .
C15 C 0.2784(3) 0.4676(2) 0.1045(3) 0.0453(7) Uani 1 1 d . . . . .
H15 H 0.2912 0.5286 0.1381 0.054 Uiso 1 1 calc R . . . .
C16 C 0.2258(4) 0.4538(2) -0.0353(3) 0.0453(7) Uani 1 1 d . . . . .
C17 C 0.2113(3) 0.3609(2) -0.0811(3) 0.0459(7) Uani 1 1 d . . . . .
C18 C 0.2428(4) 0.2834(2) 0.0059(3) 0.0439(7) Uani 1 1 d . . . . .
C19 C 0.2915(4) 0.3022(2) 0.1437(3) 0.0452(7) Uani 1 1 d . . . . .
H19 H 0.3109 0.2522 0.2037 0.054 Uiso 1 1 calc R . . . .
C20 C 0.1842(4) 0.5381(2) -0.1345(3) 0.0558(8) Uani 1 1 d . . . . .
C21 C 0.2033(7) 0.6306(3) -0.0593(5) 0.0881(16) Uani 1 1 d . . . . .
H21A H 0.1448 0.6305 -0.0107 0.132 Uiso 1 1 calc GR . . . .
H21B H 0.1746 0.6816 -0.1230 0.132 Uiso 1 1 calc GR . . . .
H21C H 0.3028 0.6382 0.0032 0.132 Uiso 1 1 calc GR . . . .
C22 C 0.2790(6) 0.5424(3) -0.2107(5) 0.0759(11) Uani 1 1 d . . . . .
H22A H 0.3786 0.5450 -0.1468 0.114 Uiso 1 1 calc GR . . . .
H22B H 0.2551 0.5975 -0.2667 0.114 Uiso 1 1 calc GR . . . .
H22C H 0.2626 0.4875 -0.2662 0.114 Uiso 1 1 calc GR . . . .
C23 C 0.0230(5) 0.5310(3) -0.2349(4) 0.0757(12) Uani 1 1 d . . . . .
H23A H 0.0087 0.4776 -0.2929 0.113 Uiso 1 1 calc GR . . . .
H23B H -0.0056 0.5872 -0.2887 0.113 Uiso 1 1 calc GR . . . .
H23C H -0.0342 0.5239 -0.1855 0.113 Uiso 1 1 calc GR . . . .
C24 C 0.2270(4) 0.1811(2) -0.0440(3) 0.0513(8) Uani 1 1 d . . . . .
C25 C 0.3293(6) 0.1620(3) -0.1102(5) 0.0766(12) Uani 1 1 d . . . . .
H25A H 0.3004 0.1991 -0.1909 0.115 Uiso 1 1 calc GR . . . .
H25B H 0.3254 0.0965 -0.1329 0.115 Uiso 1 1 calc GR . . . .
H25C H 0.4260 0.1783 -0.0482 0.115 Uiso 1 1 calc GR . . . .
C26 C 0.0719(6) 0.1602(3) -0.1459(5) 0.0828(13) Uani 1 1 d . . . . .
H26A H 0.0086 0.1678 -0.1029 0.124 Uiso 1 1 calc GR . . . .
H26B H 0.0658 0.0968 -0.1779 0.124 Uiso 1 1 calc GR . . . .
H26C H 0.0442 0.2029 -0.2209 0.124 Uiso 1 1 calc GR . . . .
C27 C 0.2683(6) 0.1122(3) 0.0744(4) 0.0798(14) Uani 1 1 d . . . . .
H27A H 0.3679 0.1210 0.1358 0.120 Uiso 1 1 calc GR . . . .
H27B H 0.2539 0.0489 0.0407 0.120 Uiso 1 1 calc GR . . . .
H27C H 0.2092 0.1236 0.1209 0.120 Uiso 1 1 calc GR . . . .
C28 C 0.6635(3) 0.3514(2) 0.8232(3) 0.0433(6) Uani 1 1 d . . . . .
C29 C 0.8106(4) 0.3561(2) 0.8969(4) 0.0550(7) Uani 1 1 d . . . . .
H29 H 0.8716 0.3508 0.8544 0.066 Uiso 1 1 calc R . . . .
C30 C 0.8665(5) 0.3688(3) 1.0355(4) 0.0695(11) Uani 1 1 d . . . . .
H30 H 0.9657 0.3717 1.0870 0.083 Uiso 1 1 calc R . . . .
C31 C 0.7755(5) 0.3772(3) 1.0975(3) 0.0705(12) Uani 1 1 d . . . . .
H31 H 0.8138 0.3864 1.1905 0.085 Uiso 1 1 calc R . . . .
C32 C 0.6301(6) 0.3721(3) 1.0239(4) 0.0689(10) Uani 1 1 d . . . . .
H32 H 0.5695 0.3772 1.0667 0.083 Uiso 1 1 calc R . . . .
C33 C 0.5722(4) 0.3592(3) 0.8848(3) 0.0551(8) Uani 1 1 d . . . . .
H33 H 0.4729 0.3559 0.8339 0.066 Uiso 1 1 calc R . . . .
N1 N 0.6015(3) 0.33605(18) 0.6793(2) 0.0459(6) Uani 1 1 d . . . . .
O1 O 0.6276(5) 0.1752(2) 0.6799(3) 0.0920(12) Uani 1 1 d . . . . .
O2 O 0.5398(3) 0.20101(18) 0.3959(3) 0.0649(7) Uani 1 1 d . . . . .
H2 H 0.5315 0.1462 0.4146 0.097 Uiso 1 1 calc GR . . . .
O3 O 0.3510(3) 0.22990(19) 0.4436(3) 0.0643(6) Uani 1 1 d . U . . .
O4 O 0.5426(3) 0.48893(16) 0.6116(2) 0.0601(7) Uani 1 1 d . . . . .
O5 O 0.1652(4) 0.34123(19) -0.2164(2) 0.0699(8) Uani 1 1 d . . . . .
H5 H 0.1954 0.3141 -0.2756 0.39(10) 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 1.543(4) . ?
C1 N1 1.382(4) . ?
C1 O1 1.197(5) . ?
C2 C3 1.548(4) . ?
C2 O2 1.376(4) . ?
C2 O3 1.423(5) . ?
C3 C4 1.543(4) . ?
C3 C5 1.543(5) . ?
C3 C7 1.548(4) . ?
C4 N1 1.397(4) . ?
C4 O4 1.198(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.521(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.498(5) . ?
C7 C14 1.533(4) . ?
C8 C9 1.382(6) . ?
C8 C13 1.389(5) . ?
C9 C10 1.394(6) . ?
C9 O3 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.401(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 C19 1.387(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.401(4) . ?
C16 C17 1.399(4) . ?
C16 C20 1.549(4) . ?
C17 C18 1.401(4) . ?
C17 O5 1.376(4) . ?
C18 C19 1.396(4) . ?
C18 C24 1.538(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.519(5) . ?
C20 C22 1.533(6) . ?
C20 C23 1.547(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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 C25 1.537(6) . ?
C24 C26 1.530(6) . ?
C24 C27 1.533(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
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 C29 1.375(5) . ?
C28 C33 1.375(5) . ?
C28 N1 1.440(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.385(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.376(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.360(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.388(5) . ?
C33 H33 0.9300 . ?
O2 H2 0.8200 . ?
O5 H5 0.9155 . ?

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
N1 C1 C2 107.3(3) . . ?
O1 C1 C2 126.2(3) . . ?
O1 C1 N1 126.5(3) . . ?
C1 C2 C3 104.4(3) . . ?
O2 C2 C1 111.0(3) . . ?
O2 C2 C3 114.0(3) . . ?
O2 C2 O3 107.3(3) . . ?
O3 C2 C1 105.3(3) . . ?
O3 C2 C3 114.5(3) . . ?
C4 C3 C2 101.9(2) . . ?
C4 C3 C5 108.1(3) . . ?
C4 C3 C7 107.5(2) . . ?
C5 C3 C2 110.8(3) . . ?
C5 C3 C7 112.8(3) . . ?
C7 C3 C2 115.0(3) . . ?
N1 C4 C3 108.6(2) . . ?
O4 C4 C3 127.4(3) . . ?
O4 C4 N1 124.0(3) . . ?
C3 C5 H5A 108.6 . . ?
C3 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C3 114.6(3) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7 107.1 . . ?
C8 C7 C3 106.8(3) . . ?
C8 C7 H7 107.1 . . ?
C8 C7 C14 112.1(3) . . ?
C14 C7 C3 116.0(2) . . ?
C14 C7 H7 107.1 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 C13 118.2(4) . . ?
C13 C8 C7 122.5(4) . . ?
C8 C9 C10 122.5(5) . . ?
O3 C9 C8 121.5(3) . . ?
O3 C9 C10 115.9(5) . . ?
C9 C10 H10 121.7 . . ?
C9 C10 C11 116.6(7) . . ?
C11 C10 H10 121.7 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.1(6) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(6) . . ?
C13 C12 H12 120.2 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(6) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C7 119.3(3) . . ?
C15 C14 C19 119.1(3) . . ?
C19 C14 C7 121.5(3) . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C20 121.2(3) . . ?
C17 C16 C15 117.1(3) . . ?
C17 C16 C20 121.7(3) . . ?
C16 C17 C18 122.8(3) . . ?
O5 C17 C16 120.8(3) . . ?
O5 C17 C18 116.4(3) . . ?
C17 C18 C24 123.0(3) . . ?
C19 C18 C17 117.1(3) . . ?
C19 C18 C24 119.9(3) . . ?
C14 C19 C18 121.9(3) . . ?
C14 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C21 C20 C16 111.0(3) . . ?
C21 C20 C22 107.2(4) . . ?
C21 C20 C23 106.9(4) . . ?
C22 C20 C16 111.4(3) . . ?
C22 C20 C23 110.6(3) . . ?
C23 C20 C16 109.6(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C18 110.3(3) . . ?
C26 C24 C18 111.1(3) . . ?
C26 C24 C25 109.3(4) . . ?
C26 C24 C27 108.3(4) . . ?
C27 C24 C18 110.8(3) . . ?
C27 C24 C25 106.8(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C33 121.2(3) . . ?
C29 C28 N1 120.4(3) . . ?
C33 C28 N1 118.4(3) . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.8(4) . . ?
C30 C29 H29 120.6 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.2(4) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.6(3) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0(4) . . ?
C33 C32 H32 120.0 . . ?
C28 C33 C32 119.2(4) . . ?
C28 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C1 N1 C4 113.0(2) . . ?
C1 N1 C28 123.2(3) . . ?
C4 N1 C28 123.7(2) . . ?
C2 O2 H2 109.5 . . ?
C9 O3 C2 119.3(3) . . ?
C17 O5 H5 141.6 . . ?

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
O2 H2 O4 0.82 2.34 3.125(4) 160.3 2_646

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 -21.2(3) . . . . ?
C1 C2 C3 C5 93.6(3) . . . . ?
C1 C2 C3 C7 -137.1(3) . . . . ?
C1 C2 O3 C9 94.9(3) . . . . ?
C2 C1 N1 C4 -6.9(4) . . . . ?
C2 C1 N1 C28 170.9(3) . . . . ?
C2 C3 C4 N1 18.2(3) . . . . ?
C2 C3 C4 O4 -163.2(4) . . . . ?
C2 C3 C5 C6 -173.9(3) . . . . ?
C2 C3 C7 C8 48.6(3) . . . . ?
C2 C3 C7 C14 -77.2(4) . . . . ?
C3 C2 O3 C9 -19.2(4) . . . . ?
C3 C4 N1 C1 -7.6(4) . . . . ?
C3 C4 N1 C28 174.7(3) . . . . ?
C3 C7 C8 C9 -38.3(4) . . . . ?
C3 C7 C8 C13 140.5(3) . . . . ?
C3 C7 C14 C15 -127.6(3) . . . . ?
C3 C7 C14 C19 56.0(4) . . . . ?
C4 C3 C5 C6 -63.1(4) . . . . ?
C4 C3 C7 C8 -64.0(3) . . . . ?
C4 C3 C7 C14 170.2(3) . . . . ?
C5 C3 C4 N1 -98.6(3) . . . . ?
C5 C3 C4 O4 80.0(4) . . . . ?
C5 C3 C7 C8 177.0(3) . . . . ?
C5 C3 C7 C14 51.2(4) . . . . ?
C7 C3 C4 N1 139.4(3) . . . . ?
C7 C3 C4 O4 -42.0(5) . . . . ?
C7 C3 C5 C6 55.6(4) . . . . ?
C7 C8 C9 C10 -178.1(3) . . . . ?
C7 C8 C9 O3 -0.7(4) . . . . ?
C7 C8 C13 C12 179.4(4) . . . . ?
C7 C14 C15 C16 -177.0(3) . . . . ?
C7 C14 C19 C18 178.5(3) . . . . ?
C8 C7 C14 C15 109.3(4) . . . . ?
C8 C7 C14 C19 -67.1(4) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C8 C9 O3 C2 33.0(4) . . . . ?
C9 C8 C13 C12 -1.7(6) . . . . ?
C9 C10 C11 C12 -2.7(7) . . . . ?
C10 C9 O3 C2 -149.4(3) . . . . ?
C10 C11 C12 C13 4.0(8) . . . . ?
C11 C12 C13 C8 -1.7(7) . . . . ?
C13 C8 C9 C10 3.0(5) . . . . ?
C13 C8 C9 O3 -179.6(3) . . . . ?
C14 C7 C8 C9 89.8(3) . . . . ?
C14 C7 C8 C13 -91.4(4) . . . . ?
C14 C15 C16 C17 -1.5(5) . . . . ?
C14 C15 C16 C20 177.9(3) . . . . ?
C15 C14 C19 C18 2.1(5) . . . . ?
C15 C16 C17 C18 2.0(5) . . . . ?
C15 C16 C17 O5 -177.7(3) . . . . ?
C15 C16 C20 C21 -2.1(5) . . . . ?
C15 C16 C20 C22 117.2(4) . . . . ?
C15 C16 C20 C23 -120.0(4) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C24 180.0(3) . . . . ?
C17 C16 C20 C21 177.2(4) . . . . ?
C17 C16 C20 C22 -63.4(4) . . . . ?
C17 C16 C20 C23 59.3(4) . . . . ?
C17 C18 C19 C14 -1.6(5) . . . . ?
C17 C18 C24 C25 62.3(5) . . . . ?
C17 C18 C24 C26 -59.1(5) . . . . ?
C17 C18 C24 C27 -179.6(4) . . . . ?
C19 C14 C15 C16 -0.5(5) . . . . ?
C19 C18 C24 C25 -117.2(4) . . . . ?
C19 C18 C24 C26 121.4(4) . . . . ?
C19 C18 C24 C27 0.9(5) . . . . ?
C20 C16 C17 C18 -177.4(3) . . . . ?
C20 C16 C17 O5 2.9(5) . . . . ?
C24 C18 C19 C14 177.9(3) . . . . ?
C28 C29 C30 C31 -0.4(5) . . . . ?
C29 C28 C33 C32 0.0(5) . . . . ?
C29 C28 N1 C1 84.6(4) . . . . ?
C29 C28 N1 C4 -97.9(4) . . . . ?
C29 C30 C31 C32 0.7(6) . . . . ?
C30 C31 C32 C33 -0.6(6) . . . . ?
C31 C32 C33 C28 0.3(6) . . . . ?
C33 C28 C29 C30 0.1(5) . . . . ?
C33 C28 N1 C1 -94.1(4) . . . . ?
C33 C28 N1 C4 83.4(4) . . . . ?
N1 C1 C2 C3 18.2(4) . . . . ?
N1 C1 C2 O2 141.5(3) . . . . ?
N1 C1 C2 O3 -102.7(3) . . . . ?
N1 C28 C29 C30 -178.6(3) . . . . ?
N1 C28 C33 C32 178.7(3) . . . . ?
O1 C1 C2 C3 -163.4(4) . . . . ?
O1 C1 C2 O2 -40.1(6) . . . . ?
O1 C1 C2 O3 75.7(5) . . . . ?
O1 C1 N1 C4 174.7(4) . . . . ?
O1 C1 N1 C28 -7.5(6) . . . . ?
O2 C2 C3 C4 -142.6(3) . . . . ?
O2 C2 C3 C5 -27.8(4) . . . . ?
O2 C2 C3 C7 101.6(3) . . . . ?
O2 C2 O3 C9 -146.8(3) . . . . ?
O3 C2 C3 C4 93.4(3) . . . . ?
O3 C2 C3 C5 -151.8(3) . . . . ?
O3 C2 C3 C7 -22.5(4) . . . . ?
O3 C9 C10 C11 -178.4(4) . . . . ?
O4 C4 N1 C1 173.8(4) . . . . ?
O4 C4 N1 C28 -4.0(5) . . . . ?
O5 C17 C18 C19 179.2(3) . . . . ?
O5 C17 C18 C24 -0.3(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_201909219
_database_code_depnum_ccdc_archive 'CCDC 1991274'
loop_
_audit_author_name
_audit_author_address
'Xiang Min'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu
China
;
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_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         
'C33 H37 N O5, C0.7 H0.7 Cl1.55, C0.3 H0.3 Cl1.45'
_chemical_formula_sum            'C34 H38 Cl3 N O5'
_chemical_formula_weight         647.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4b
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5380(6)
_cell_length_b                   12.9179(10)
_cell_length_c                   13.0658(9)
_cell_angle_alpha                98.879(6)
_cell_angle_beta                 105.364(6)
_cell_angle_gamma                95.484(6)
_cell_volume                     1677.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6750
_cell_measurement_theta_min      4.4870
_shelx_estimated_absorpt_T_max   0.767
_shelx_estimated_absorpt_T_min   0.578
_exptl_absorpt_coefficient_mu    2.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81539
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.571
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 150.00   76
  2  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00 120.00   98
  3  ω    -46.00   0.00   1.00    1.00    --  -33.50 -19.00  90.00   46
  4  ω    -86.00 -60.00   1.00    1.00    --  -33.50 -57.00  30.00   26
  5  ω     57.00 109.00   1.00    1.00    --   36.47 178.00  30.00   52
  6  ω     57.00 109.00   1.00    1.00    --   36.47 178.00 120.00   52
  7  ω     18.00 107.00   1.00    1.00    --   36.47  37.00-120.00   89
  8  ω    -33.00  18.00   1.00    1.00    --   36.47 -77.00 -30.00   51
  9  ω     36.00  65.00   1.00    1.00    --   36.47 -77.00 -30.00   29
 10  ω    -34.00  47.00   1.00    1.00    --   36.47 -37.00  60.00   81
 11  ω     58.00  91.00   1.00    1.00    --   36.47 178.00  90.00   33
 12  ω     68.00  94.00   1.00    1.00    --   36.47 178.00   0.00   26
 13  ω     40.00 100.00   1.00    1.00    --   36.47-140.00-122.00   60
 14  ω    103.00 128.00   1.00    5.50    --  108.00 -45.00 150.00   25
 15  ω     39.00  90.00   1.00    5.50    --  108.00 -45.00 150.00   51
 16  ω     46.00  72.00   1.00    5.50    --  108.00 -61.00 120.00   26
 17  ω     39.00 114.00   1.00    5.50    --  108.00 -45.00 -30.00   75
 18  ω     64.00 169.00   1.00    5.50    --  108.00  15.00-150.00  105
 19  ω     38.00 120.00   1.00    5.50    --  108.00 -45.00  60.00   82
 20  ω     64.00 111.00   1.00    5.50    --  108.00-111.00-150.00   47
 21  ω    120.00 176.00   1.00    5.50    --  108.00  61.00  90.00   56
 22  ω     37.00 111.00   1.00    5.50    --  108.00-111.00 -30.00   74
 23  ω     88.00 121.00   1.00    5.50    --  108.00  45.00   0.00   33
 24  ω    116.00 165.00   1.00    5.50    --  108.00  61.00  30.00   49
 25  ω     46.00 110.00   1.00    5.50    --  108.00 -94.00  90.00   64
 26  ω     61.00 103.00   1.00    5.50    --  108.00-111.00  60.00   42
 27  ω     96.00 153.00   1.00    5.50    --  108.00  45.00 120.00   57
 28  ω     97.00 126.00   1.00    5.50    --  108.00  45.00  90.00   29
 29  ω     69.00 140.00   1.00    5.50    --  108.00 178.00   0.00   71
 30  ω     41.00  85.00   1.00    5.50    --  108.00 -61.00 -60.00   44
;
_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      -0.0669125000
_diffrn_orient_matrix_UB_12      -0.0073482000
_diffrn_orient_matrix_UB_13      -0.1214847000
_diffrn_orient_matrix_UB_21      -0.0235141000
_diffrn_orient_matrix_UB_22      -0.1216385000
_diffrn_orient_matrix_UB_23      -0.0151017000
_diffrn_orient_matrix_UB_31      -0.1357816000
_diffrn_orient_matrix_UB_32      0.0049762000
_diffrn_orient_matrix_UB_33      0.0225429000
_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                4283
_reflns_number_total             6004
_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 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         0.440
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.039
_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)+(0.1136P)²+0.4778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2204
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Cl2A)
Uanis(C34) = Uanis(C34A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(Cl3) = Uanis(Cl3A)
3. Others
 Sof(C34A)=Sof(H34A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(C34)=Sof(H34)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(Cl3A)=1-FVAR(2)
 Sof(Cl3)=FVAR(2)
4.a Riding coordinates:
 O5(H5a)
4.b Ternary CH refined with riding coordinates:
 C5(H5), C34(H34), C34A(H34A)
4.c Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C25(H25)
4.e Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c), C29(H29a,H29b,
 H29c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.5626(3) 0.9253(2) 0.3508(2) 0.0410(6) Uani 1 1 d . . . . .
C2 C 0.4421(3) 0.8568(2) 0.3641(2) 0.0397(6) Uani 1 1 d . . . . .
C3 C 0.4013(3) 0.7663(2) 0.2637(2) 0.0391(6) Uani 1 1 d . . . . .
C4 C 0.4749(3) 0.8068(2) 0.1889(2) 0.0426(6) Uani 1 1 d . . . . .
C5 C 0.4553(3) 0.6630(2) 0.2946(2) 0.0438(6) Uani 1 1 d . . . . .
H5 H 0.4073 0.6048 0.2353 0.053 Uiso 1 1 calc R . . . .
C6 C 0.4131(3) 0.6434(3) 0.3925(3) 0.0527(7) Uani 1 1 d . . . . .
C7 C 0.4277(3) 0.7289(3) 0.4741(3) 0.0536(7) Uani 1 1 d . . . . .
C8 C 0.3925(4) 0.7196(4) 0.5681(3) 0.0777(12) Uani 1 1 d . . . . .
H8 H 0.4027 0.7786 0.6220 0.093 Uiso 1 1 calc R . . . .
C9 C 0.3423(5) 0.6215(6) 0.5794(5) 0.1015(19) Uani 1 1 d . . . . .
H9 H 0.3206 0.6134 0.6425 0.122 Uiso 1 1 calc R . . . .
C10 C 0.3236(4) 0.5351(5) 0.4987(6) 0.1003(19) Uani 1 1 d . . . . .
H10 H 0.2876 0.4693 0.5068 0.120 Uiso 1 1 calc R . . . .
C11 C 0.3584(4) 0.5455(3) 0.4046(4) 0.0767(12) Uani 1 1 d . . . . .
H11 H 0.3450 0.4868 0.3498 0.092 Uiso 1 1 calc R . . . .
C12 C 0.2503(3) 0.7400(2) 0.2085(2) 0.0471(6) Uani 1 1 d . . . . .
H12A H 0.2335 0.6710 0.1619 0.057 Uiso 1 1 calc R . . . .
H12B H 0.2063 0.7338 0.2642 0.057 Uiso 1 1 calc R . . . .
C13 C 0.1851(4) 0.8173(3) 0.1417(3) 0.0700(10) Uani 1 1 d . . . . .
H13A H 0.2221 0.8203 0.0824 0.105 Uiso 1 1 calc GR . . . .
H13B H 0.2009 0.8863 0.1862 0.105 Uiso 1 1 calc GR . . . .
H13C H 0.0911 0.7939 0.1144 0.105 Uiso 1 1 calc GR . . . .
C14 C 0.6613(3) 0.9471(2) 0.2022(2) 0.0462(6) Uani 1 1 d . . . . .
C15 C 0.7786(4) 0.9098(3) 0.2061(4) 0.0722(10) Uani 1 1 d . . . . .
H15 H 0.7982 0.8509 0.2369 0.087 Uiso 1 1 calc R . . . .
C16 C 0.8689(4) 0.9614(5) 0.1632(4) 0.0955(15) Uani 1 1 d . . . . .
H16 H 0.9503 0.9376 0.1668 0.115 Uiso 1 1 calc R . . . .
C17 C 0.8398(5) 1.0452(4) 0.1166(4) 0.0907(14) Uani 1 1 d . . . . .
H17 H 0.8998 1.0778 0.0864 0.109 Uiso 1 1 calc R . . . .
C18 C 0.7232(6) 1.0821(5) 0.1135(5) 0.1080(18) Uani 1 1 d . . . . .
H18 H 0.7044 1.1412 0.0827 0.130 Uiso 1 1 calc R . . . .
C19 C 0.6323(5) 1.0330(4) 0.1555(4) 0.0857(13) Uani 1 1 d . . . . .
H19 H 0.5517 1.0580 0.1522 0.103 Uiso 1 1 calc R . . . .
C20 C 0.6040(3) 0.6600(2) 0.3083(2) 0.0409(6) Uani 1 1 d . . . . .
C21 C 0.6404(3) 0.5988(2) 0.2264(2) 0.0441(6) Uani 1 1 d . . . . .
H21 H 0.5740 0.5640 0.1650 0.053 Uiso 1 1 calc R . . . .
C22 C 0.7718(3) 0.5874(2) 0.2322(2) 0.0438(6) Uani 1 1 d . . . . .
C23 C 0.8688(3) 0.6403(2) 0.3265(2) 0.0473(6) Uani 1 1 d . . . . .
C24 C 0.8379(3) 0.7069(2) 0.4095(2) 0.0439(6) Uani 1 1 d . . . . .
C25 C 0.7038(3) 0.7140(2) 0.3988(2) 0.0427(6) Uani 1 1 d . . . . .
H25 H 0.6805 0.7560 0.4536 0.051 Uiso 1 1 calc R . . . .
C26 C 0.8076(3) 0.5210(3) 0.1388(3) 0.0560(8) Uani 1 1 d . . . . .
C27 C 0.6844(4) 0.4801(4) 0.0421(4) 0.0866(14) Uani 1 1 d . . . . .
H27A H 0.6202 0.4376 0.0641 0.130 Uiso 1 1 calc GR . . . .
H27B H 0.7096 0.4381 -0.0146 0.130 Uiso 1 1 calc GR . . . .
H27C H 0.6462 0.5391 0.0162 0.130 Uiso 1 1 calc GR . . . .
C28 C 0.8704(6) 0.4261(4) 0.1744(4) 0.1004(16) Uani 1 1 d . . . . .
H28A H 0.9464 0.4502 0.2362 0.151 Uiso 1 1 calc GR . . . .
H28B H 0.8978 0.3884 0.1165 0.151 Uiso 1 1 calc GR . . . .
H28C H 0.8067 0.3799 0.1930 0.151 Uiso 1 1 calc GR . . . .
C29 C 0.9019(4) 0.5897(4) 0.0975(3) 0.0844(13) Uani 1 1 d . . . . .
H29A H 0.8574 0.6446 0.0683 0.127 Uiso 1 1 calc GR . . . .
H29B H 0.9285 0.5468 0.0422 0.127 Uiso 1 1 calc GR . . . .
H29C H 0.9790 0.6209 0.1561 0.127 Uiso 1 1 calc GR . . . .
C30 C 0.9458(3) 0.7703(3) 0.5101(3) 0.0621(8) Uani 1 1 d . . . . .
C31 C 1.0133(5) 0.6947(5) 0.5800(3) 0.0887(13) Uani 1 1 d . . . . .
H31A H 0.9476 0.6529 0.6011 0.133 Uiso 1 1 calc GR . . . .
H31B H 1.0781 0.7350 0.6434 0.133 Uiso 1 1 calc GR . . . .
H31C H 1.0564 0.6489 0.5393 0.133 Uiso 1 1 calc GR . . . .
C32 C 1.0492(4) 0.8412(4) 0.4780(4) 0.0929(14) Uani 1 1 d . . . . .
H32A H 1.1037 0.7979 0.4471 0.139 Uiso 1 1 calc GR . . . .
H32B H 1.1040 0.8897 0.5409 0.139 Uiso 1 1 calc GR . . . .
H32C H 1.0043 0.8803 0.4260 0.139 Uiso 1 1 calc GR . . . .
C33 C 0.8848(4) 0.8448(4) 0.5812(4) 0.0936(16) Uani 1 1 d . . . . .
H33A H 0.8377 0.8912 0.5391 0.140 Uiso 1 1 calc GR . . . .
H33B H 0.9542 0.8860 0.6408 0.140 Uiso 1 1 calc GR . . . .
H33C H 0.8243 0.8038 0.6080 0.140 Uiso 1 1 calc GR . . . .
N1 N 0.5671(2) 0.89608(18) 0.24641(18) 0.0412(5) Uani 1 1 d . . . . .
O1 O 0.6381(2) 0.99371(18) 0.41844(18) 0.0581(6) Uani 1 1 d . . . . .
O2 O 0.3405(2) 0.91829(17) 0.36527(17) 0.0513(5) Uani 1 1 d . . . . .
H2 H 0.3573 0.9571 0.4245 0.077 Uiso 1 1 calc GR . . . .
O3 O 0.4860(2) 0.82707(17) 0.46603(15) 0.0482(5) Uani 1 1 d . . . . .
O4 O 0.4619(2) 0.76915(19) 0.09662(17) 0.0601(6) Uani 1 1 d . . . . .
O5 O 0.9983(2) 0.6243(2) 0.3340(2) 0.0719(7) Uani 1 1 d . . . . .
H5A H 1.0628 0.6402 0.3294 0.48(11) Uiso 1 1 d R . . . .
C34 C 0.3139(11) 0.2362(8) 0.1836(10) 0.116(3) Uani 0.698(4) 1 d . . P A 1
H34 H 0.3713 0.2587 0.2579 0.140 Uiso 0.698(4) 1 calc R . P A 1
C34A C 0.262(3) 0.201(2) 0.110(2) 0.116(3) Uani 0.302(4) 1 d . . P A 2
H34A H 0.2462 0.1632 0.0357 0.140 Uiso 0.302(4) 1 calc R . P A 2
Cl1 Cl 0.1665(4) 0.2945(3) 0.1660(3) 0.1212(10) Uani 0.698(4) 1 d . . P A 1
Cl1A Cl 0.1530(10) 0.2565(8) 0.1247(7) 0.1212(10) Uani 0.302(4) 1 d . . P A 2
Cl2 Cl 0.4024(3) 0.2474(3) 0.0937(3) 0.1387(13) Uani 0.698(4) 1 d . . P A 1
Cl2A Cl 0.4227(9) 0.3037(7) 0.1580(8) 0.1387(13) Uani 0.302(4) 1 d . . P A 2
Cl3 Cl 0.253(2) 0.1086(12) 0.161(2) 0.1211(12) Uani 0.157(12) 1 d . . P A 1
Cl3A Cl 0.3035(5) 0.11016(18) 0.2136(5) 0.1211(12) Uani 0.843(12) 1 d . . P A 2


_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 1.542(4) . ?
C1 N1 1.373(4) . ?
C1 O1 1.202(4) . ?
C2 C3 1.551(4) . ?
C2 O2 1.394(3) . ?
C2 O3 1.414(3) . ?
C3 C4 1.520(4) . ?
C3 C5 1.568(4) . ?
C3 C12 1.542(4) . ?
C4 N1 1.404(4) . ?
C4 O4 1.195(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.510(4) . ?
C5 C20 1.535(4) . ?
C6 C7 1.377(5) . ?
C6 C11 1.388(5) . ?
C7 C8 1.393(5) . ?
C7 O3 1.387(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(7) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.521(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.361(5) . ?
C14 C19 1.368(5) . ?
C14 N1 1.431(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.343(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(4) . ?
C20 C25 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.390(4) . ?
C22 C23 1.404(4) . ?
C22 C26 1.533(4) . ?
C23 C24 1.405(4) . ?
C23 O5 1.379(4) . ?
C24 C25 1.396(4) . ?
C24 C30 1.546(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.535(5) . ?
C26 C28 1.525(6) . ?
C26 C29 1.526(5) . ?
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 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.536(6) . ?
C30 C32 1.540(6) . ?
C30 C33 1.536(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O2 H2 0.8200 . ?
O5 H5A 0.7115 . ?
C34 H34 0.9800 . ?
C34 Cl1 1.766(10) . ?
C34 Cl2 1.697(10) . ?
C34 Cl3 1.662(19) . ?
C34A H34A 0.9800 . ?
C34A Cl1A 1.45(3) . ?
C34A Cl2A 1.94(3) . ?
C34A Cl3A 1.91(2) . ?

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
N1 C1 C2 107.7(2) . . ?
O1 C1 C2 126.7(2) . . ?
O1 C1 N1 125.7(3) . . ?
C1 C2 C3 104.6(2) . . ?
O2 C2 C1 109.1(2) . . ?
O2 C2 C3 111.2(2) . . ?
O2 C2 O3 109.0(2) . . ?
O3 C2 C1 105.8(2) . . ?
O3 C2 C3 116.7(2) . . ?
C2 C3 C5 110.2(2) . . ?
C4 C3 C2 103.1(2) . . ?
C4 C3 C5 108.3(2) . . ?
C4 C3 C12 111.5(2) . . ?
C12 C3 C2 114.7(2) . . ?
C12 C3 C5 108.7(2) . . ?
N1 C4 C3 109.1(2) . . ?
O4 C4 C3 127.1(3) . . ?
O4 C4 N1 123.7(3) . . ?
C3 C5 H5 106.6 . . ?
C6 C5 C3 107.1(2) . . ?
C6 C5 H5 106.6 . . ?
C6 C5 C20 113.3(2) . . ?
C20 C5 C3 116.2(2) . . ?
C20 C5 H5 106.6 . . ?
C7 C6 C5 117.6(3) . . ?
C7 C6 C11 118.1(3) . . ?
C11 C6 C5 124.3(4) . . ?
C6 C7 C8 122.3(4) . . ?
C6 C7 O3 119.5(3) . . ?
O3 C7 C8 118.1(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.4(5) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.3(4) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 120.0(5) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C3 C12 H12A 108.0 . . ?
C3 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C13 C12 C3 117.4(3) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.3(3) . . ?
C15 C14 N1 120.1(3) . . ?
C19 C14 N1 119.7(3) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.5(4) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C5 118.0(2) . . ?
C21 C20 C25 118.5(2) . . ?
C25 C20 C5 123.5(2) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 C20 122.8(3) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 C23 116.8(3) . . ?
C21 C22 C26 121.0(3) . . ?
C23 C22 C26 122.2(2) . . ?
C22 C23 C24 122.6(3) . . ?
O5 C23 C22 116.5(3) . . ?
O5 C23 C24 121.0(3) . . ?
C23 C24 C30 122.5(3) . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 C30 120.0(3) . . ?
C20 C25 C24 121.7(3) . . ?
C20 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C22 C26 C27 111.4(3) . . ?
C28 C26 C22 110.8(3) . . ?
C28 C26 C27 108.4(4) . . ?
C28 C26 C29 110.5(4) . . ?
C29 C26 C22 109.7(3) . . ?
C29 C26 C27 105.9(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C24 110.2(3) . . ?
C31 C30 C32 110.8(4) . . ?
C31 C30 C33 107.0(4) . . ?
C32 C30 C24 111.3(3) . . ?
C33 C30 C24 111.1(3) . . ?
C33 C30 C32 106.2(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1 N1 C4 113.1(2) . . ?
C1 N1 C14 123.7(2) . . ?
C4 N1 C14 123.1(2) . . ?
C2 O2 H2 109.5 . . ?
C7 O3 C2 115.6(2) . . ?
C23 O5 H5A 151.8 . . ?
Cl1 C34 H34 110.7 . . ?
Cl2 C34 H34 110.7 . . ?
Cl2 C34 Cl1 117.8(6) . . ?
Cl3 C34 H34 110.7 . . ?
Cl3 C34 Cl1 100.9(10) . . ?
Cl3 C34 Cl2 105.4(9) . . ?
Cl1A C34A H34A 112.6 . . ?
Cl1A C34A Cl2A 107.4(16) . . ?
Cl1A C34A Cl3A 110.4(15) . . ?
Cl2A C34A H34A 112.6 . . ?
Cl3A C34A H34A 112.6 . . ?
Cl3A C34A Cl2A 100.6(13) . . ?

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
O2 H2 O1 0.82 2.04 2.820(3) 159.0 2_676

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 -14.9(3) . . . . ?
C1 C2 C3 C5 100.6(2) . . . . ?
C1 C2 C3 C12 -136.3(2) . . . . ?
C1 C2 O3 C7 -148.1(2) . . . . ?
C2 C1 N1 C4 -7.5(3) . . . . ?
C2 C1 N1 C14 176.0(2) . . . . ?
C2 C3 C4 N1 11.3(3) . . . . ?
C2 C3 C4 O4 -170.8(3) . . . . ?
C2 C3 C5 C6 51.1(3) . . . . ?
C2 C3 C5 C20 -76.6(3) . . . . ?
C2 C3 C12 C13 74.5(3) . . . . ?
C3 C2 O3 C7 -32.2(3) . . . . ?
C3 C4 N1 C1 -2.6(3) . . . . ?
C3 C4 N1 C14 173.9(2) . . . . ?
C3 C5 C6 C7 -44.0(3) . . . . ?
C3 C5 C6 C11 134.7(3) . . . . ?
C3 C5 C20 C21 -104.4(3) . . . . ?
C3 C5 C20 C25 76.4(3) . . . . ?
C4 C3 C5 C6 163.2(2) . . . . ?
C4 C3 C5 C20 35.5(3) . . . . ?
C4 C3 C12 C13 -42.3(4) . . . . ?
C5 C3 C4 N1 -105.5(2) . . . . ?
C5 C3 C4 O4 72.4(4) . . . . ?
C5 C3 C12 C13 -161.6(3) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C5 C6 C7 O3 -3.3(4) . . . . ?
C5 C6 C11 C10 179.4(3) . . . . ?
C5 C20 C21 C22 -177.7(3) . . . . ?
C5 C20 C25 C24 178.3(3) . . . . ?
C6 C5 C20 C21 131.0(3) . . . . ?
C6 C5 C20 C25 -48.2(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C6 C7 O3 C2 44.6(4) . . . . ?
C7 C6 C11 C10 -1.9(5) . . . . ?
C7 C8 C9 C10 -1.9(7) . . . . ?
C8 C7 O3 C2 -138.7(3) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C9 C10 C11 C6 0.5(7) . . . . ?
C11 C6 C7 C8 1.4(5) . . . . ?
C11 C6 C7 O3 177.9(3) . . . . ?
C12 C3 C4 N1 134.9(2) . . . . ?
C12 C3 C4 O4 -47.1(4) . . . . ?
C12 C3 C5 C6 -75.4(3) . . . . ?
C12 C3 C5 C20 156.8(2) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C14 C19 C18 -0.6(7) . . . . ?
C15 C14 N1 C1 91.9(4) . . . . ?
C15 C14 N1 C4 -84.2(4) . . . . ?
C15 C16 C17 C18 1.8(9) . . . . ?
C16 C17 C18 C19 -1.6(9) . . . . ?
C17 C18 C19 C14 1.0(9) . . . . ?
C19 C14 C15 C16 0.8(6) . . . . ?
C19 C14 N1 C1 -88.4(4) . . . . ?
C19 C14 N1 C4 95.5(4) . . . . ?
C20 C5 C6 C7 85.4(3) . . . . ?
C20 C5 C6 C11 -95.9(4) . . . . ?
C20 C21 C22 C23 0.7(4) . . . . ?
C20 C21 C22 C26 -178.7(3) . . . . ?
C21 C20 C25 C24 -0.9(4) . . . . ?
C21 C22 C23 C24 -3.7(4) . . . . ?
C21 C22 C23 O5 176.9(3) . . . . ?
C21 C22 C26 C27 4.3(5) . . . . ?
C21 C22 C26 C28 -116.5(4) . . . . ?
C21 C22 C26 C29 121.2(3) . . . . ?
C22 C23 C24 C25 4.3(4) . . . . ?
C22 C23 C24 C30 -176.2(3) . . . . ?
C23 C22 C26 C27 -175.1(3) . . . . ?
C23 C22 C26 C28 64.2(4) . . . . ?
C23 C22 C26 C29 -58.2(4) . . . . ?
C23 C24 C25 C20 -1.9(4) . . . . ?
C23 C24 C30 C31 -67.4(4) . . . . ?
C23 C24 C30 C32 55.9(5) . . . . ?
C23 C24 C30 C33 174.1(4) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
C25 C24 C30 C31 112.1(3) . . . . ?
C25 C24 C30 C32 -124.5(4) . . . . ?
C25 C24 C30 C33 -6.3(5) . . . . ?
C26 C22 C23 C24 175.7(3) . . . . ?
C26 C22 C23 O5 -3.8(4) . . . . ?
C30 C24 C25 C20 178.6(3) . . . . ?
N1 C1 C2 C3 14.2(3) . . . . ?
N1 C1 C2 O2 -104.9(2) . . . . ?
N1 C1 C2 O3 138.0(2) . . . . ?
N1 C14 C15 C16 -179.5(4) . . . . ?
N1 C14 C19 C18 179.7(5) . . . . ?
O1 C1 C2 C3 -167.3(3) . . . . ?
O1 C1 C2 O2 73.7(4) . . . . ?
O1 C1 C2 O3 -43.4(4) . . . . ?
O1 C1 N1 C4 173.9(3) . . . . ?
O1 C1 N1 C14 -2.6(5) . . . . ?
O2 C2 C3 C4 102.7(2) . . . . ?
O2 C2 C3 C5 -141.8(2) . . . . ?
O2 C2 C3 C12 -18.8(3) . . . . ?
O2 C2 O3 C7 94.8(3) . . . . ?
O3 C2 C3 C4 -131.4(2) . . . . ?
O3 C2 C3 C5 -16.0(3) . . . . ?
O3 C2 C3 C12 107.1(3) . . . . ?
O3 C7 C8 C9 -176.1(3) . . . . ?
O4 C4 N1 C1 179.3(3) . . . . ?
O4 C4 N1 C14 -4.2(5) . . . . ?
O5 C23 C24 C25 -176.3(3) . . . . ?
O5 C23 C24 C30 3.3(5) . . . . ?

_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.847
