# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_caoj_0528
_database_code_depnum_ccdc_archive 'CCDC 1848528'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;
_audit_creation_date             2018-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C33 H32 Cl N O9'
_chemical_formula_sum            'C33 H32 Cl N O9'
_chemical_formula_weight         622.05
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   11.0158(17)
_cell_length_b                   12.1300(16)
_cell_length_c                   23.587(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3151.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    295.19(10)
_cell_measurement_theta_max      19.5340
_cell_measurement_theta_min      3.8220
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8253
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_temperature      295.19(10)
_diffrn_detector_area_resol_mean 16.0733
_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   -4.00   23.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00   52.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  120.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0548484000
_diffrn_orient_matrix_UB_12      -0.0286169000
_diffrn_orient_matrix_UB_13      0.0056244000
_diffrn_orient_matrix_UB_21      0.0311794000
_diffrn_orient_matrix_UB_22      0.0509674000
_diffrn_orient_matrix_UB_23      0.0024730000
_diffrn_orient_matrix_UB_31      -0.0131082000
_diffrn_orient_matrix_UB_32      0.0011516000
_diffrn_orient_matrix_UB_33      0.0294199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2366
_reflns_number_total             5621
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.312
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.1754
_refine_ls_R_factor_gt           0.0917
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1185P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2924
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1A-N1
 0.82 with sigma of 0.01
 C20-C19
 1.45 with sigma of 0.01
 C22-C23
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O9) \\sim Ueq, Uanis(O8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O8) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C22(H22A,H22B), C19(H19A,H19B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C17(H17), C15(H15), C4(H4), C13(H13), C16(H16), C29(H29),
 C14(H14), C27(H27), C30(H30), C31(H31), C28(H28)
4.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.8730(2) 0.2597(2) 0.19340(10) 0.1094(8) Uani 1 d . . . .
O4 O 1.0009(4) 0.2384(4) -0.0230(2) 0.0746(13) Uani 1 d . . . .
O1 O 1.1727(5) 0.2978(4) 0.0267(3) 0.0838(16) Uani 1 d . . . .
O2 O 1.2379(5) 0.4168(5) -0.0598(3) 0.0976(18) Uani 1 d . . . .
O3 O 1.0573(5) 0.3946(4) -0.1013(2) 0.0856(16) Uani 1 d . . . .
C8 C 1.0754(7) 0.3299(6) -0.0086(3) 0.0710(19) Uani 1 d . . . .
O7 O 1.0850(7) 0.5111(6) 0.1913(3) 0.111(2) Uani 1 d . . . .
C1 C 0.9398(7) 0.3601(7) 0.0776(3) 0.080(2) Uani 1 d . . . .
H1 H 0.8639 0.3204 0.0704 0.096 Uiso 1 calc . . R .
C12 C 1.0105(8) 0.6106(7) -0.0063(3) 0.082(2) Uani 1 d . . . .
C7 C 1.1399(7) 0.2536(7) 0.0795(4) 0.083(2) Uani 1 d . . . .
C26 C 1.0096(7) 0.4580(7) -0.1961(4) 0.082(2) Uani 1 d . . . .
C2 C 1.0315(7) 0.2821(7) 0.1055(4) 0.078(2) Uani 1 d . . . .
C9 C 0.9878(7) 0.4089(6) 0.0220(3) 0.074(2) Uani 1 d . . . .
H9 H 0.9181 0.4212 -0.0031 0.089 Uiso 1 calc . . R .
C6 C 1.2245(8) 0.1825(7) 0.1037(5) 0.091(3) Uani 1 d . . . .
H6 H 1.2971 0.1658 0.0855 0.109 Uiso 1 calc . . R .
C32 C 1.0483(9) 0.1591(7) -0.0590(4) 0.089(2) Uani 1 d . . . .
C5 C 1.1962(9) 0.1383(8) 0.1556(5) 0.102(3) Uani 1 d . . . .
H5 H 1.2524 0.0926 0.1733 0.122 Uiso 1 calc . . R .
C17 C 1.0978(9) 0.6719(7) -0.0339(4) 0.094(3) Uani 1 d . . . .
H17 H 1.1795 0.6594 -0.0263 0.113 Uiso 1 calc . . R .
O8 O 0.8529(10) 0.6748(7) 0.1231(4) 0.165(4) Uani 1 d . . . U
C15 C 0.9474(13) 0.7729(7) -0.0847(5) 0.110(3) Uani 1 d . . . .
H15 H 0.9265 0.8257 -0.1116 0.132 Uiso 1 calc . . R .
C21 C 1.1214(10) 0.5304(7) 0.1374(5) 0.093(3) Uani 1 d . . . .
C25 C 1.1063(9) 0.4539(9) -0.1510(4) 0.109(3) Uani 1 d . . . .
H25A H 1.1775 0.4160 -0.1654 0.131 Uiso 1 calc . . R .
H25B H 1.1298 0.5281 -0.1403 0.131 Uiso 1 calc . . R .
C4 C 1.0887(10) 0.1591(8) 0.1821(4) 0.099(3) Uani 1 d . . . .
H4 H 1.0702 0.1249 0.2163 0.119 Uiso 1 calc . . R .
O9 O 1.0399(9) 0.7320(6) 0.1057(3) 0.139(3) Uani 1 d . . . U
C13 C 0.8873(9) 0.6331(8) -0.0185(4) 0.103(3) Uani 1 d . . . .
H13 H 0.8262 0.5927 -0.0009 0.124 Uiso 1 calc . . R .
O6 O 1.2205(7) 0.5340(6) 0.1224(3) 0.119(2) Uani 1 d . . . .
C3 C 1.0086(7) 0.2308(7) 0.1579(4) 0.084(2) Uani 1 d . . . .
O5 O 1.1481(6) 0.1671(6) -0.0784(3) 0.121(3) Uani 1 d . . . .
C24 C 1.1362(8) 0.3829(6) -0.0588(4) 0.077(2) Uani 1 d . . . .
C16 C 1.0642(12) 0.7528(8) -0.0733(4) 0.110(3) Uani 1 d . . . .
H16 H 1.1241 0.7931 -0.0917 0.131 Uiso 1 calc . . R .
C18 C 0.9531(13) 0.6570(9) 0.1094(5) 0.117(4) Uani 1 d . . . .
C10 C 1.0451(8) 0.5222(6) 0.0349(3) 0.077(2) Uani 1 d . . . .
H10 H 1.1335 0.5137 0.0336 0.092 Uiso 1 calc . . R .
C11 C 1.0075(8) 0.5421(7) 0.0989(3) 0.082(2) Uani 1 d . . . .
C29 C 0.8617(16) 0.4586(17) -0.2855(6) 0.169(5) Uani 1 d . . . U
H29 H 0.8176 0.4614 -0.3191 0.203 Uiso 1 calc . . R .
N1 N 0.9142(6) 0.4603(7) 0.1121(3) 0.088(2) Uani 1 d . . D .
H1A H 0.847(4) 0.461(8) 0.097(3) 0.106 Uiso 1 d . . DR .
C33 C 0.9589(9) 0.0735(7) -0.0691(5) 0.126(4) Uani 1 d . . . .
H33A H 0.9224 0.0523 -0.0338 0.188 Uiso 1 calc . . GR .
H33B H 0.9978 0.0107 -0.0860 0.188 Uiso 1 calc . . GR .
H33C H 0.8973 0.1008 -0.0943 0.188 Uiso 1 calc . . GR .
C22 C 1.1856(14) 0.4990(13) 0.2286(6) 0.160(5) Uani 1 d . . D U
H22A H 1.2589 0.5168 0.2078 0.192 Uiso 1 calc . . R .
H22B H 1.1775 0.5529 0.2587 0.192 Uiso 1 calc . . R .
C14 C 0.8581(11) 0.7152(8) -0.0566(4) 0.111(3) Uani 1 d . . . .
H14 H 0.7770 0.7319 -0.0634 0.134 Uiso 1 calc . . R .
C27 C 0.9911(12) 0.3674(9) -0.2292(5) 0.118(4) Uani 1 d . . . .
H27 H 1.0343 0.3034 -0.2213 0.142 Uiso 1 calc . . R .
C30 C 0.8678(17) 0.5558(14) -0.2512(7) 0.179(6) Uani 1 d . . . U
H30 H 0.8201 0.6174 -0.2585 0.215 Uiso 1 calc . . R .
C31 C 0.9505(11) 0.5524(9) -0.2057(6) 0.143(5) Uani 1 d . . . .
H31 H 0.9636 0.6141 -0.1831 0.172 Uiso 1 calc . . R .
C28 C 0.9141(16) 0.3674(15) -0.2722(7) 0.161(5) Uani 1 d . . . U
H28 H 0.8982 0.3030 -0.2922 0.194 Uiso 1 calc . . R .
C20 C 1.0019(17) 0.9143(12) 0.0707(6) 0.206(7) Uani 1 d . . D U
H20A H 1.0785 0.9330 0.0539 0.309 Uiso 1 calc . . GR .
H20B H 0.9583 0.9806 0.0797 0.309 Uiso 1 calc . . GR .
H20C H 0.9553 0.8711 0.0445 0.309 Uiso 1 calc . . GR .
C19 C 1.0218(17) 0.8525(11) 0.1212(6) 0.183(6) Uani 1 d . . D U
H19A H 0.9526 0.8599 0.1463 0.220 Uiso 1 calc . . R .
H19B H 1.0931 0.8800 0.1407 0.220 Uiso 1 calc . . R .
C23 C 1.2011(19) 0.3951(13) 0.2534(8) 0.243(9) Uani 1 d . . D U
H23A H 1.1288 0.3752 0.2737 0.364 Uiso 1 calc . . GR .
H23B H 1.2685 0.3974 0.2792 0.364 Uiso 1 calc . . GR .
H23C H 1.2167 0.3415 0.2244 0.364 Uiso 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
Cl1 C3 1.748(9) . ?
O4 C8 1.422(8) . ?
O4 C32 1.385(9) . ?
O1 C8 1.411(9) . ?
O1 C7 1.403(10) . ?
O2 C24 1.194(9) . ?
O3 C25 1.479(10) . ?
O3 C24 1.332(10) . ?
C8 C9 1.538(10) . ?
C8 C24 1.506(11) . ?
O7 C21 1.352(12) . ?
O7 C22 1.423(13) . ?
C1 H1 0.9800 . ?
C1 C2 1.532(11) . ?
C1 C9 1.534(11) . ?
C1 N1 1.490(11) . ?
C12 C17 1.378(11) . ?
C12 C13 1.414(12) . ?
C12 C10 1.498(11) . ?
C7 C2 1.385(10) . ?
C7 C6 1.392(11) . ?
C26 C25 1.505(12) . ?
C26 C27 1.365(12) . ?
C26 C31 1.337(14) . ?
C2 C3 1.407(11) . ?
C9 H9 0.9800 . ?
C9 C10 1.543(10) . ?
C6 H6 0.9300 . ?
C6 C5 1.373(13) . ?
C32 O5 1.195(10) . ?
C32 C33 1.451(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.362(13) . ?
C17 H17 0.9300 . ?
C17 C16 1.401(13) . ?
O8 C18 1.171(13) . ?
C15 H15 0.9300 . ?
C15 C16 1.337(15) . ?
C15 C14 1.378(14) . ?
C21 O6 1.148(11) . ?
C21 C11 1.555(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.364(11) . ?
O9 C18 1.323(14) . ?
O9 C19 1.519(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(13) . ?
C16 H16 0.9300 . ?
C18 C11 1.537(12) . ?
C10 H10 0.9800 . ?
C10 C11 1.583(11) . ?
C11 N1 1.463(11) . ?
C29 H29 0.9300 . ?
C29 C30 1.43(2) . ?
C29 C28 1.287(19) . ?
N1 H1A 0.819(11) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.400(9) . ?
C14 H14 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.321(17) . ?
C30 H30 0.9300 . ?
C30 C31 1.407(17) . ?
C31 H31 0.9300 . ?
C28 H28 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C19 1.425(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C32 O4 C8 118.1(6) . . ?
C7 O1 C8 115.7(6) . . ?
C24 O3 C25 114.2(7) . . ?
O4 C8 C9 103.6(5) . . ?
O4 C8 C24 113.7(6) . . ?
O1 C8 O4 111.3(6) . . ?
O1 C8 C9 111.9(6) . . ?
O1 C8 C24 104.2(7) . . ?
C24 C8 C9 112.5(6) . . ?
C21 O7 C22 111.6(9) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 C9 112.2(7) . . ?
C9 C1 H1 109.5 . . ?
N1 C1 H1 109.5 . . ?
N1 C1 C2 113.2(6) . . ?
N1 C1 C9 102.6(7) . . ?
C17 C12 C13 118.1(9) . . ?
C17 C12 C10 121.0(8) . . ?
C13 C12 C10 120.9(8) . . ?
C2 C7 O1 121.3(8) . . ?
C2 C7 C6 123.4(9) . . ?
C6 C7 O1 115.3(8) . . ?
C27 C26 C25 118.9(10) . . ?
C31 C26 C25 119.6(10) . . ?
C31 C26 C27 121.3(10) . . ?
C7 C2 C1 122.2(8) . . ?
C7 C2 C3 115.6(8) . . ?
C3 C2 C1 122.1(7) . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C10 113.0(6) . . ?
C1 C9 C8 112.1(6) . . ?
C1 C9 H9 107.7 . . ?
C1 C9 C10 108.3(6) . . ?
C10 C9 H9 107.7 . . ?
C7 C6 H6 121.5 . . ?
C5 C6 C7 117.1(9) . . ?
C5 C6 H6 121.5 . . ?
O4 C32 C33 110.0(7) . . ?
O5 C32 O4 121.7(7) . . ?
O5 C32 C33 128.2(8) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 C6 122.3(9) . . ?
C4 C5 H5 118.9 . . ?
C12 C17 H17 119.8 . . ?
C12 C17 C16 120.4(10) . . ?
C16 C17 H17 119.8 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.8(11) . . ?
C14 C15 H15 120.1 . . ?
O7 C21 C11 109.0(9) . . ?
O6 C21 O7 125.3(11) . . ?
O6 C21 C11 125.6(11) . . ?
O3 C25 C26 108.6(7) . . ?
O3 C25 H25A 110.0 . . ?
O3 C25 H25B 110.0 . . ?
C26 C25 H25A 110.0 . . ?
C26 C25 H25B 110.0 . . ?
H25A C25 H25B 108.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.2(10) . . ?
C3 C4 H4 120.4 . . ?
C18 O9 C19 123.4(11) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(9) . . ?
C14 C13 H13 120.2 . . ?
C2 C3 Cl1 119.1(6) . . ?
C4 C3 Cl1 118.7(8) . . ?
C4 C3 C2 122.3(8) . . ?
O2 C24 O3 124.1(9) . . ?
O2 C24 C8 125.4(9) . . ?
O3 C24 C8 110.3(7) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.1(11) . . ?
C15 C16 H16 119.5 . . ?
O8 C18 O9 124.9(10) . . ?
O8 C18 C11 125.5(12) . . ?
O9 C18 C11 109.3(10) . . ?
C12 C10 C9 113.9(6) . . ?
C12 C10 H10 107.9 . . ?
C12 C10 C11 116.3(6) . . ?
C9 C10 H10 107.9 . . ?
C9 C10 C11 102.6(7) . . ?
C11 C10 H10 107.9 . . ?
C21 C11 C10 109.4(7) . . ?
C18 C11 C21 107.7(8) . . ?
C18 C11 C10 113.2(7) . . ?
N1 C11 C21 112.4(7) . . ?
N1 C11 C18 107.9(8) . . ?
N1 C11 C10 106.4(6) . . ?
C30 C29 H29 118.4 . . ?
C28 C29 H29 118.4 . . ?
C28 C29 C30 123.2(16) . . ?
C1 N1 H1A 87(7) . . ?
C11 N1 C1 107.7(6) . . ?
C11 N1 H1A 123(7) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O7 C22 H22A 108.2 . . ?
O7 C22 H22B 108.2 . . ?
H22A C22 H22B 107.3 . . ?
C23 C22 O7 116.6(13) . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C15 C14 C13 121.0(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C26 C27 H27 118.8 . . ?
C28 C27 C26 122.4(14) . . ?
C28 C27 H27 118.8 . . ?
C29 C30 H30 122.0 . . ?
C31 C30 C29 115.9(15) . . ?
C31 C30 H30 122.0 . . ?
C26 C31 C30 118.0(13) . . ?
C26 C31 H31 121.0 . . ?
C30 C31 H31 121.0 . . ?
C29 C28 C27 118.4(17) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
O9 C19 H19A 109.9 . . ?
O9 C19 H19B 109.9 . . ?
C20 C19 O9 109.0(11) . . ?
C20 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O4 C8 C9 C1 64.7(8) . . . . ?
O4 C8 C9 C10 -172.5(6) . . . . ?
O4 C8 C24 O2 -140.2(8) . . . . ?
O4 C8 C24 O3 44.6(8) . . . . ?
O1 C8 C9 C1 -55.3(8) . . . . ?
O1 C8 C9 C10 67.5(9) . . . . ?
O1 C8 C24 O2 -18.9(10) . . . . ?
O1 C8 C24 O3 165.9(6) . . . . ?
O1 C7 C2 C1 1.9(11) . . . . ?
O1 C7 C2 C3 179.1(6) . . . . ?
O1 C7 C6 C5 179.5(7) . . . . ?
C8 O4 C32 O5 -1.0(13) . . . . ?
C8 O4 C32 C33 -179.4(8) . . . . ?
C8 O1 C7 C2 -26.8(10) . . . . ?
C8 O1 C7 C6 154.6(6) . . . . ?
C8 C9 C10 C12 99.8(8) . . . . ?
C8 C9 C10 C11 -133.6(7) . . . . ?
O7 C21 C11 C18 76.6(10) . . . . ?
O7 C21 C11 C10 -160.0(7) . . . . ?
O7 C21 C11 N1 -42.0(9) . . . . ?
C1 C2 C3 Cl1 -1.7(10) . . . . ?
C1 C2 C3 C4 178.2(8) . . . . ?
C1 C9 C10 C12 -135.3(7) . . . . ?
C1 C9 C10 C11 -8.7(8) . . . . ?
C12 C17 C16 C15 0.5(14) . . . . ?
C12 C13 C14 C15 2.6(15) . . . . ?
C12 C10 C11 C21 -126.5(8) . . . . ?
C12 C10 C11 C18 -6.4(12) . . . . ?
C12 C10 C11 N1 111.9(7) . . . . ?
C7 O1 C8 O4 -62.2(8) . . . . ?
C7 O1 C8 C9 53.2(8) . . . . ?
C7 O1 C8 C24 174.9(6) . . . . ?
C7 C2 C3 Cl1 -178.9(6) . . . . ?
C7 C2 C3 C4 1.0(12) . . . . ?
C7 C6 C5 C4 2.2(14) . . . . ?
C26 C27 C28 C29 5(2) . . . . ?
C2 C1 C9 C8 30.4(9) . . . . ?
C2 C1 C9 C10 -95.0(7) . . . . ?
C2 C1 N1 C11 85.2(8) . . . . ?
C2 C7 C6 C5 0.9(12) . . . . ?
C9 C8 C24 O2 102.5(9) . . . . ?
C9 C8 C24 O3 -72.8(7) . . . . ?
C9 C1 C2 C7 -5.2(10) . . . . ?
C9 C1 C2 C3 177.7(7) . . . . ?
C9 C1 N1 C11 -35.9(8) . . . . ?
C9 C10 C11 C21 108.5(8) . . . . ?
C9 C10 C11 C18 -131.4(9) . . . . ?
C9 C10 C11 N1 -13.1(8) . . . . ?
C6 C7 C2 C1 -179.6(7) . . . . ?
C6 C7 C2 C3 -2.4(11) . . . . ?
C6 C5 C4 C3 -3.5(15) . . . . ?
C32 O4 C8 O1 -69.6(9) . . . . ?
C32 O4 C8 C9 170.0(7) . . . . ?
C32 O4 C8 C24 47.6(9) . . . . ?
C5 C4 C3 Cl1 -178.2(7) . . . . ?
C5 C4 C3 C2 1.8(14) . . . . ?
C17 C12 C13 C14 -0.6(14) . . . . ?
C17 C12 C10 C9 -126.3(8) . . . . ?
C17 C12 C10 C11 114.7(9) . . . . ?
O8 C18 C11 C21 -124.5(13) . . . . ?
O8 C18 C11 C10 114.5(13) . . . . ?
O8 C18 C11 N1 -3.0(15) . . . . ?
C21 O7 C22 C23 -114.7(17) . . . . ?
C21 C11 N1 C1 -88.5(8) . . . . ?
C25 O3 C24 O2 0.2(11) . . . . ?
C25 O3 C24 C8 175.5(6) . . . . ?
C25 C26 C27 C28 -175.1(11) . . . . ?
C25 C26 C31 C30 174.9(11) . . . . ?
O9 C18 C11 C21 49.6(12) . . . . ?
O9 C18 C11 C10 -71.4(11) . . . . ?
O9 C18 C11 N1 171.2(8) . . . . ?
C13 C12 C17 C16 -0.9(12) . . . . ?
C13 C12 C10 C9 53.2(11) . . . . ?
C13 C12 C10 C11 -65.8(11) . . . . ?
O6 C21 C11 C18 -105.7(11) . . . . ?
O6 C21 C11 C10 17.7(13) . . . . ?
O6 C21 C11 N1 135.7(10) . . . . ?
C24 O3 C25 C26 178.3(7) . . . . ?
C24 C8 C9 C1 -172.1(6) . . . . ?
C24 C8 C9 C10 -49.3(9) . . . . ?
C16 C15 C14 C13 -3.0(16) . . . . ?
C18 O9 C19 C20 -99.3(16) . . . . ?
C18 C11 N1 C1 153.0(7) . . . . ?
C10 C12 C17 C16 178.6(7) . . . . ?
C10 C12 C13 C14 179.9(8) . . . . ?
C10 C11 N1 C1 31.3(8) . . . . ?
C29 C30 C31 C26 -4(2) . . . . ?
N1 C1 C2 C7 -120.8(8) . . . . ?
N1 C1 C2 C3 62.2(10) . . . . ?
N1 C1 C9 C8 152.3(6) . . . . ?
N1 C1 C9 C10 26.9(8) . . . . ?
C22 O7 C21 O6 1.9(15) . . . . ?
C22 O7 C21 C11 179.6(9) . . . . ?
C14 C15 C16 C17 1.5(16) . . . . ?
C27 C26 C25 O3 -79.9(10) . . . . ?
C27 C26 C31 C30 0.2(18) . . . . ?
C30 C29 C28 C27 -10(3) . . . . ?
C31 C26 C25 O3 105.3(11) . . . . ?
C31 C26 C27 C28 -0.4(18) . . . . ?
C28 C29 C30 C31 10(3) . . . . ?
C19 O9 C18 O8 2(2) . . . . ?
C19 O9 C18 C11 -171.7(9) . . . . ?


_olex2_date_sample_data_collection 2018-05-28
_olex2_submission_special_instructions 'No special instructions were received'
