# Electronic Supplementary Material (ESI) for ChemComm.
# 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_210316_s2_mj_hbtz0310
_audit_block_doi                 10.5517/ccdc.csd.cc295f86
_database_code_depnum_ccdc_archive 'CCDC 2120377'
loop_
_audit_author_name
_audit_author_address
zhoutian
;Chengdu University of TCM
China
;
_audit_update_record             
;
2022-03-03 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H35 N4 O8'
_chemical_formula_sum            'C32 H34 N4 O8'
_chemical_formula_weight         602.63
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.4403(9)
_cell_length_b                   12.4980(11)
_cell_length_c                   27.612(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3257.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9860
_cell_measurement_theta_min      3.4910
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18281
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00  -21.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  109.0000 -167.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   31.00   61.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086 -109.0000   96.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -76.00  -35.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   23.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega  -79.00  -52.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -81.00  -31.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -27.00   -1.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -73.00  -35.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000 -150.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0095799000
_diffrn_orient_matrix_UB_12      0.0336808000
_diffrn_orient_matrix_UB_13      -0.0204053000
_diffrn_orient_matrix_UB_21      0.0150938000
_diffrn_orient_matrix_UB_22      0.0453804000
_diffrn_orient_matrix_UB_23      0.0145227000
_diffrn_orient_matrix_UB_31      0.0730130000
_diffrn_orient_matrix_UB_32      -0.0050355000
_diffrn_orient_matrix_UB_33      -0.0056876000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4442
_reflns_number_total             6615
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_coef       0.0055(19)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6615
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.040
_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)+(0.0867P)²+0.9873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C16 = C15-C16A
 1.55 with sigma of 0.02
3. Rigid bond restraints
 C15, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C15 \\sim C18: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(C17) = Uanis(C17A)
Uanis(C16) = Uanis(C16A)
Uanis(C16A) = Uanis(C16) = Uanis(C17A) = Uanis(C17)
5. Others
 Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C4(H4A), C5(H5), C6(H6), C7(H7), C13(H13), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32)
6.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C16(H16A,H16B,H16C), C17(H17A,
 H17B,H17C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F)
;
_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 0.1498(4) 0.7559(3) 0.32328(12) 0.0608(10) Uani 1 1 d . . . . .
O2 O 0.3049(6) 0.9412(4) 0.4360(2) 0.135(3) Uani 1 1 d . . . . .
O3 O 0.1386(5) 0.9247(3) 0.38148(17) 0.0843(14) Uani 1 1 d . . . . .
O4 O 0.4208(5) 0.5687(4) 0.24027(14) 0.0934(15) Uani 1 1 d . . . . .
O5 O 0.4821(4) 0.6830(3) 0.30049(12) 0.0602(10) Uani 1 1 d . . . . .
O6 O 0.2915(4) 0.3704(3) 0.39450(13) 0.0640(10) Uani 1 1 d . . . . .
O7 O -0.1059(5) 0.4186(4) 0.36716(14) 0.0926(16) Uani 1 1 d . . . . .
O8 O -0.0627(5) 0.3926(4) 0.28891(14) 0.0996(18) Uani 1 1 d . . . . .
N1 N 0.2844(4) 0.7876(3) 0.39311(14) 0.0481(9) Uani 1 1 d . . . . .
N2 N 0.3091(4) 0.5658(3) 0.31285(13) 0.0520(10) Uani 1 1 d . . . . .
N3 N 0.1636(4) 0.4528(3) 0.45579(13) 0.0451(9) Uani 1 1 d . . . . .
N4 N 0.0669(4) 0.5390(3) 0.45842(13) 0.0464(9) Uani 1 1 d . . . . .
H4 H 0.0202 0.5571 0.4839 0.056 Uiso 1 1 calc R U . . .
C1 C 0.2267(5) 0.7271(4) 0.35527(16) 0.0457(11) Uani 1 1 d . . . . .
C2 C 0.2822(5) 0.6115(4) 0.36176(15) 0.0433(11) Uani 1 1 d . . . . .
C3 C 0.4015(5) 0.6253(4) 0.39710(16) 0.0454(11) Uani 1 1 d . . . . .
C4 C 0.5060(5) 0.5555(4) 0.41145(19) 0.0579(13) Uani 1 1 d . . . . .
H4A H 0.5131 0.4878 0.3977 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6014(6) 0.5887(5) 0.4472(2) 0.0695(16) Uani 1 1 d . . . . .
H5 H 0.6719 0.5422 0.4577 0.083 Uiso 1 1 calc R U . . .
C6 C 0.5916(6) 0.6892(5) 0.4666(2) 0.0688(16) Uani 1 1 d . . . . .
H6 H 0.6561 0.7098 0.4903 0.083 Uiso 1 1 calc R U . . .
C7 C 0.4879(5) 0.7615(5) 0.45206(18) 0.0593(14) Uani 1 1 d . . . . .
H7 H 0.4812 0.8293 0.4658 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3952(5) 0.7284(4) 0.41634(16) 0.0461(11) Uani 1 1 d . . . . .
C9 C 0.1566(5) 0.5364(3) 0.38030(15) 0.0430(10) Uani 1 1 d . . . . .
C10 C 0.0594(5) 0.5859(3) 0.41744(15) 0.0422(10) Uani 1 1 d . . . . .
C11 C 0.2165(5) 0.4417(3) 0.41025(17) 0.0471(11) Uani 1 1 d . . . . .
C12 C 0.0973(6) 0.4941(4) 0.33327(17) 0.0524(13) Uani 1 1 d . . . . .
C13 C 0.1909(6) 0.5090(4) 0.29804(18) 0.0592(14) Uani 1 1 d . . . . .
H13 H 0.1784 0.4839 0.2666 0.071 Uiso 1 1 calc R U . . .
C14 C 0.2467(6) 0.8940(4) 0.4048(2) 0.0576(13) Uani 1 1 d . . . . .
C15 C 0.0698(10) 1.0301(5) 0.3858(4) 0.112(2) Uani 1 1 d D U . . .
C18 C 0.1695(11) 1.1153(6) 0.3762(4) 0.125(2) Uani 1 1 d . U . . .
H18A H 0.2440 1.1134 0.3999 0.188 Uiso 1 1 calc R U . . .
H18B H 0.1216 1.1830 0.3779 0.188 Uiso 1 1 calc R U . . .
H18C H 0.2090 1.1062 0.3444 0.188 Uiso 1 1 calc R U . . .
C19 C 0.4082(6) 0.6044(4) 0.28020(19) 0.0603(14) Uani 1 1 d . . . . .
C20 C 0.6171(6) 0.7224(5) 0.2786(2) 0.0736(17) Uani 1 1 d . . . . .
C21 C 0.6628(9) 0.8045(6) 0.3149(3) 0.106(3) Uani 1 1 d . . . . .
H21A H 0.5923 0.8597 0.3170 0.159 Uiso 1 1 calc R U . . .
H21B H 0.7513 0.8352 0.3050 0.159 Uiso 1 1 calc R U . . .
H21C H 0.6739 0.7711 0.3460 0.159 Uiso 1 1 calc R U . . .
C22 C 0.5861(9) 0.7700(6) 0.2293(2) 0.099(2) Uani 1 1 d . . . . .
H22A H 0.5487 0.7155 0.2083 0.148 Uiso 1 1 calc R U . . .
H22B H 0.6719 0.7981 0.2156 0.148 Uiso 1 1 calc R U . . .
H22C H 0.5180 0.8265 0.2326 0.148 Uiso 1 1 calc R U . . .
C23 C 0.7181(8) 0.6280(8) 0.2771(3) 0.127(3) Uani 1 1 d . . . . .
H23A H 0.7152 0.5911 0.3076 0.190 Uiso 1 1 calc R U . . .
H23B H 0.8126 0.6532 0.2712 0.190 Uiso 1 1 calc R U . . .
H23C H 0.6903 0.5800 0.2517 0.190 Uiso 1 1 calc R U . . .
C24 C -0.0334(7) 0.4327(5) 0.33238(19) 0.0643(15) Uani 1 1 d . . . . .
C25 C -0.1924(10) 0.3312(8) 0.2852(3) 0.139(4) Uani 1 1 d . . . . .
H25A H -0.2297 0.3373 0.2530 0.209 Uiso 1 1 calc R U . . .
H25B H -0.2605 0.3582 0.3080 0.209 Uiso 1 1 calc R U . . .
H25C H -0.1730 0.2574 0.2922 0.209 Uiso 1 1 calc R U . . .
C26 C -0.0458(6) 0.6742(4) 0.4102(2) 0.0587(13) Uani 1 1 d . . . . .
H26A H -0.0897 0.6912 0.4406 0.088 Uiso 1 1 calc R U . . .
H26B H -0.1168 0.6515 0.3875 0.088 Uiso 1 1 calc R U . . .
H26C H 0.0018 0.7363 0.3978 0.088 Uiso 1 1 calc R U . . .
C27 C 0.1724(5) 0.3823(4) 0.49598(16) 0.0473(11) Uani 1 1 d . . . . .
C28 C 0.0813(6) 0.3944(5) 0.5344(2) 0.0699(16) Uani 1 1 d . . . . .
H28 H 0.0153 0.4496 0.5347 0.084 Uiso 1 1 calc R U . . .
C29 C 0.0894(8) 0.3233(6) 0.5726(2) 0.087(2) Uani 1 1 d . . . . .
H29 H 0.0278 0.3316 0.5986 0.105 Uiso 1 1 calc R U . . .
C30 C 0.1839(8) 0.2420(6) 0.5735(2) 0.0828(19) Uani 1 1 d . . . . .
H30 H 0.1873 0.1951 0.5996 0.099 Uiso 1 1 calc R U . . .
C31 C 0.2740(7) 0.2302(5) 0.5353(2) 0.0766(17) Uani 1 1 d . . . . .
H31 H 0.3390 0.1743 0.5355 0.092 Uiso 1 1 calc R U . . .
C32 C 0.2707(7) 0.2994(4) 0.4966(2) 0.0660(15) Uani 1 1 d . . . . .
H32 H 0.3338 0.2909 0.4710 0.079 Uiso 1 1 calc R U . . .
C16 C -0.030(2) 1.0084(17) 0.4284(7) 0.124(4) Uani 0.484(12) 1 d D . P A 1
H16A H -0.1141 0.9743 0.4168 0.187 Uiso 0.484(12) 1 calc R U P A 1
H16B H -0.0537 1.0748 0.4437 0.187 Uiso 0.484(12) 1 calc R U P A 1
H16C H 0.0168 0.9625 0.4513 0.187 Uiso 0.484(12) 1 calc R U P A 1
C17 C -0.013(3) 1.0356(18) 0.3356(8) 0.124(4) Uani 0.484(12) 1 d . . P A 1
H17A H 0.0536 1.0418 0.3095 0.187 Uiso 0.484(12) 1 calc R U P A 1
H17B H -0.0749 1.0966 0.3356 0.187 Uiso 0.484(12) 1 calc R U P A 1
H17C H -0.0681 0.9716 0.3315 0.187 Uiso 0.484(12) 1 calc R U P A 1
C16A C 0.056(2) 1.0695(17) 0.4391(6) 0.124(4) Uani 0.516(12) 1 d D . P A 2
H16D H -0.0376 1.0962 0.4446 0.187 Uiso 0.516(12) 1 calc R U P A 2
H16E H 0.1238 1.1255 0.4449 0.187 Uiso 0.516(12) 1 calc R U P A 2
H16F H 0.0747 1.0110 0.4608 0.187 Uiso 0.516(12) 1 calc R U P A 2
C17A C -0.073(2) 1.0225(18) 0.3620(8) 0.124(4) Uani 0.516(12) 1 d . . P A 2
H17D H -0.0654 0.9827 0.3324 0.187 Uiso 0.516(12) 1 calc R U P A 2
H17E H -0.1080 1.0931 0.3551 0.187 Uiso 0.516(12) 1 calc R U P A 2
H17F H -0.1383 0.9868 0.3834 0.187 Uiso 0.516(12) 1 calc R U 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
O1 C1 1.199(6) . ?
O2 C14 1.179(6) . ?
O3 C14 1.267(7) . ?
O3 C15 1.473(8) . ?
O4 C19 1.195(6) . ?
O5 C19 1.329(6) . ?
O5 C20 1.495(7) . ?
O6 C11 1.219(6) . ?
O7 C24 1.192(6) . ?
O8 C24 1.330(6) . ?
O8 C25 1.449(8) . ?
N1 C1 1.400(6) . ?
N1 C8 1.433(6) . ?
N1 C14 1.414(6) . ?
N2 C2 1.488(5) . ?
N2 C13 1.385(6) . ?
N2 C19 1.385(6) . ?
N3 N4 1.413(5) . ?
N3 C11 1.360(6) . ?
N3 C27 1.420(6) . ?
N4 H4 0.8600 . ?
N4 C10 1.276(6) . ?
C1 C2 1.548(7) . ?
C2 C3 1.500(7) . ?
C2 C9 1.597(6) . ?
C3 C4 1.375(7) . ?
C3 C8 1.395(7) . ?
C4 H4A 0.9300 . ?
C4 C5 1.398(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(7) . ?
C9 C10 1.509(6) . ?
C9 C11 1.550(7) . ?
C9 C12 1.510(6) . ?
C10 C26 1.498(7) . ?
C12 C13 1.327(7) . ?
C12 C24 1.454(7) . ?
C13 H13 0.9300 . ?
C15 C18 1.446(12) . ?
C15 C16 1.527(18) . ?
C15 C17 1.59(2) . ?
C15 C16A 1.557(16) . ?
C15 C17A 1.51(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 C21 1.498(10) . ?
C20 C22 1.514(9) . ?
C20 C23 1.517(10) . ?
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 . ?
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 C28 1.373(7) . ?
C27 C32 1.391(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.353(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.362(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(8) . ?
C32 H32 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 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
C14 O3 C15 125.8(5) . . ?
C19 O5 C20 121.4(4) . . ?
C24 O8 C25 116.0(5) . . ?
C1 N1 C8 109.8(4) . . ?
C1 N1 C14 125.5(4) . . ?
C14 N1 C8 124.6(4) . . ?
C13 N2 C2 109.1(4) . . ?
C13 N2 C19 122.0(4) . . ?
C19 N2 C2 124.9(4) . . ?
N4 N3 C27 118.1(4) . . ?
C11 N3 N4 111.2(4) . . ?
C11 N3 C27 129.6(4) . . ?
N3 N4 H4 125.1 . . ?
C10 N4 N3 109.9(3) . . ?
C10 N4 H4 125.1 . . ?
O1 C1 N1 128.6(4) . . ?
O1 C1 C2 124.8(4) . . ?
N1 C1 C2 106.6(4) . . ?
N2 C2 C1 108.1(4) . . ?
N2 C2 C3 120.4(4) . . ?
N2 C2 C9 101.1(3) . . ?
C1 C2 C9 109.6(4) . . ?
C3 C2 C1 102.8(4) . . ?
C3 C2 C9 114.6(4) . . ?
C4 C3 C2 130.8(4) . . ?
C4 C3 C8 120.5(5) . . ?
C8 C3 C2 108.8(4) . . ?
C3 C4 H4A 120.8 . . ?
C3 C4 C5 118.5(5) . . ?
C5 C4 H4A 120.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 122.0(5) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.2(5) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 109.8(4) . . ?
C7 C8 N1 128.8(5) . . ?
C7 C8 C3 121.5(5) . . ?
C10 C9 C2 115.3(3) . . ?
C10 C9 C11 99.9(4) . . ?
C10 C9 C12 120.2(4) . . ?
C11 C9 C2 110.4(4) . . ?
C12 C9 C2 101.9(3) . . ?
C12 C9 C11 109.1(4) . . ?
N4 C10 C9 112.3(4) . . ?
N4 C10 C26 119.6(4) . . ?
C26 C10 C9 127.9(4) . . ?
O6 C11 N3 128.2(5) . . ?
O6 C11 C9 125.4(4) . . ?
N3 C11 C9 106.4(4) . . ?
C13 C12 C9 109.5(5) . . ?
C13 C12 C24 128.9(5) . . ?
C24 C12 C9 120.9(4) . . ?
N2 C13 H13 123.5 . . ?
C12 C13 N2 113.1(4) . . ?
C12 C13 H13 123.5 . . ?
O2 C14 O3 126.5(5) . . ?
O2 C14 N1 121.3(5) . . ?
O3 C14 N1 111.8(4) . . ?
O3 C15 C16 100.1(9) . . ?
O3 C15 C17 100.6(9) . . ?
O3 C15 C16A 113.3(9) . . ?
O3 C15 C17A 107.7(9) . . ?
C18 C15 O3 110.9(7) . . ?
C18 C15 C16 132.2(12) . . ?
C18 C15 C17 97.4(12) . . ?
C18 C15 C16A 89.7(11) . . ?
C18 C15 C17A 123.4(12) . . ?
C16 C15 C17 112.0(14) . . ?
C17A C15 C16A 111.0(12) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O5 127.8(5) . . ?
O4 C19 N2 122.5(5) . . ?
O5 C19 N2 109.7(4) . . ?
O5 C20 C21 101.5(5) . . ?
O5 C20 C22 109.2(5) . . ?
O5 C20 C23 106.8(5) . . ?
C21 C20 C22 112.9(6) . . ?
C21 C20 C23 111.7(6) . . ?
C22 C20 C23 113.8(6) . . ?
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 . . ?
O7 C24 O8 123.5(5) . . ?
O7 C24 C12 123.5(5) . . ?
O8 C24 C12 113.0(5) . . ?
O8 C25 H25A 109.5 . . ?
O8 C25 H25B 109.5 . . ?
O8 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C10 C26 H26A 109.5 . . ?
C10 C26 H26B 109.5 . . ?
C10 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N3 119.9(4) . . ?
C28 C27 C32 119.4(5) . . ?
C32 C27 N3 120.7(4) . . ?
C27 C28 H28 120.5 . . ?
C27 C28 C29 118.9(6) . . ?
C29 C28 H28 120.5 . . ?
C28 C29 H29 118.8 . . ?
C30 C29 C28 122.3(6) . . ?
C30 C29 H29 118.8 . . ?
C29 C30 H30 120.7 . . ?
C29 C30 C31 118.6(6) . . ?
C31 C30 H30 120.7 . . ?
C30 C31 H31 119.3 . . ?
C30 C31 C32 121.3(6) . . ?
C32 C31 H31 119.3 . . ?
C27 C32 H32 120.3 . . ?
C31 C32 C27 119.5(6) . . ?
C31 C32 H32 120.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C16A H16D 109.5 . . ?
C15 C16A H16E 109.5 . . ?
C15 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15 C17A H17D 109.5 . . ?
C15 C17A H17E 109.5 . . ?
C15 C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 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 N2 36.5(6) . . . . ?
O1 C1 C2 C3 164.9(4) . . . . ?
O1 C1 C2 C9 -72.8(5) . . . . ?
N1 C1 C2 N2 -143.2(4) . . . . ?
N1 C1 C2 C3 -14.8(4) . . . . ?
N1 C1 C2 C9 107.5(4) . . . . ?
N2 C2 C3 C4 -48.3(7) . . . . ?
N2 C2 C3 C8 131.8(4) . . . . ?
N2 C2 C9 C10 -153.8(4) . . . . ?
N2 C2 C9 C11 93.9(4) . . . . ?
N2 C2 C9 C12 -21.9(4) . . . . ?
N3 N4 C10 C9 -1.1(5) . . . . ?
N3 N4 C10 C26 174.8(4) . . . . ?
N3 C27 C28 C29 178.5(6) . . . . ?
N3 C27 C32 C31 -178.0(5) . . . . ?
N4 N3 C11 O6 -172.7(5) . . . . ?
N4 N3 C11 C9 4.6(5) . . . . ?
N4 N3 C27 C28 4.6(6) . . . . ?
N4 N3 C27 C32 -176.6(4) . . . . ?
C1 N1 C8 C3 -5.8(5) . . . . ?
C1 N1 C8 C7 173.5(5) . . . . ?
C1 N1 C14 O2 -176.6(6) . . . . ?
C1 N1 C14 O3 9.7(7) . . . . ?
C1 C2 C3 C4 -168.5(5) . . . . ?
C1 C2 C3 C8 11.6(5) . . . . ?
C1 C2 C9 C10 -39.9(5) . . . . ?
C1 C2 C9 C11 -152.2(4) . . . . ?
C1 C2 C9 C12 92.1(4) . . . . ?
C2 N2 C13 C12 -11.0(6) . . . . ?
C2 N2 C19 O4 -175.8(6) . . . . ?
C2 N2 C19 O5 4.5(7) . . . . ?
C2 C3 C4 C5 -177.2(5) . . . . ?
C2 C3 C8 N1 -4.4(5) . . . . ?
C2 C3 C8 C7 176.3(4) . . . . ?
C2 C9 C10 N4 -114.8(4) . . . . ?
C2 C9 C10 C26 69.8(6) . . . . ?
C2 C9 C11 O6 -65.4(6) . . . . ?
C2 C9 C11 N3 117.2(4) . . . . ?
C2 C9 C12 C13 17.3(5) . . . . ?
C2 C9 C12 C24 -171.4(5) . . . . ?
C3 C2 C9 C10 75.1(5) . . . . ?
C3 C2 C9 C11 -37.2(5) . . . . ?
C3 C2 C9 C12 -153.0(4) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C4 C3 C8 N1 175.7(4) . . . . ?
C4 C3 C8 C7 -3.6(7) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
C6 C7 C8 N1 -176.6(5) . . . . ?
C6 C7 C8 C3 2.6(7) . . . . ?
C8 N1 C1 O1 -166.7(5) . . . . ?
C8 N1 C1 C2 13.0(5) . . . . ?
C8 N1 C14 O2 -1.2(9) . . . . ?
C8 N1 C14 O3 -175.0(4) . . . . ?
C8 C3 C4 C5 2.8(7) . . . . ?
C9 C2 C3 C4 72.7(6) . . . . ?
C9 C2 C3 C8 -107.2(4) . . . . ?
C9 C12 C13 N2 -5.0(6) . . . . ?
C9 C12 C24 O7 5.4(9) . . . . ?
C9 C12 C24 O8 -173.6(5) . . . . ?
C10 C9 C11 O6 172.7(5) . . . . ?
C10 C9 C11 N3 -4.8(4) . . . . ?
C10 C9 C12 C13 146.2(5) . . . . ?
C10 C9 C12 C24 -42.5(7) . . . . ?
C11 N3 N4 C10 -2.4(5) . . . . ?
C11 N3 C27 C28 -162.5(5) . . . . ?
C11 N3 C27 C32 16.3(7) . . . . ?
C11 C9 C10 N4 3.6(5) . . . . ?
C11 C9 C10 C26 -171.9(5) . . . . ?
C11 C9 C12 C13 -99.5(5) . . . . ?
C11 C9 C12 C24 71.9(6) . . . . ?
C12 C9 C10 N4 122.6(5) . . . . ?
C12 C9 C10 C26 -52.8(7) . . . . ?
C12 C9 C11 O6 45.8(6) . . . . ?
C12 C9 C11 N3 -131.7(4) . . . . ?
C13 N2 C2 C1 -94.5(5) . . . . ?
C13 N2 C2 C3 148.0(4) . . . . ?
C13 N2 C2 C9 20.5(5) . . . . ?
C13 N2 C19 O4 -20.7(9) . . . . ?
C13 N2 C19 O5 159.6(5) . . . . ?
C13 C12 C24 O7 175.0(7) . . . . ?
C13 C12 C24 O8 -4.1(9) . . . . ?
C14 O3 C15 C18 56.7(11) . . . . ?
C14 O3 C15 C16 -86.2(12) . . . . ?
C14 O3 C15 C17 158.9(12) . . . . ?
C14 O3 C15 C16A -42.4(14) . . . . ?
C14 O3 C15 C17A -165.5(11) . . . . ?
C14 N1 C1 O1 9.3(8) . . . . ?
C14 N1 C1 C2 -171.1(4) . . . . ?
C14 N1 C8 C3 178.3(4) . . . . ?
C14 N1 C8 C7 -2.5(7) . . . . ?
C15 O3 C14 O2 5.3(11) . . . . ?
C15 O3 C14 N1 178.6(6) . . . . ?
C19 O5 C20 C21 -177.2(5) . . . . ?
C19 O5 C20 C22 63.3(7) . . . . ?
C19 O5 C20 C23 -60.1(7) . . . . ?
C19 N2 C2 C1 63.3(6) . . . . ?
C19 N2 C2 C3 -54.3(7) . . . . ?
C19 N2 C2 C9 178.3(5) . . . . ?
C19 N2 C13 C12 -169.6(5) . . . . ?
C20 O5 C19 O4 -14.1(9) . . . . ?
C20 O5 C19 N2 165.5(5) . . . . ?
C24 C12 C13 N2 -175.4(5) . . . . ?
C25 O8 C24 O7 1.5(11) . . . . ?
C25 O8 C24 C12 -179.5(7) . . . . ?
C27 N3 N4 C10 -171.8(4) . . . . ?
C27 N3 C11 O6 -4.9(8) . . . . ?
C27 N3 C11 C9 172.4(4) . . . . ?
C27 C28 C29 C30 0.0(11) . . . . ?
C28 C27 C32 C31 0.8(8) . . . . ?
C28 C29 C30 C31 0.0(11) . . . . ?
C29 C30 C31 C32 0.4(10) . . . . ?
C30 C31 C32 C27 -0.9(9) . . . . ?
C32 C27 C28 C29 -0.4(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
