# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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 
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data_sliu24_ga100k
_database_code_depnum_ccdc_archive 'CCDC 2368440'
loop_
_audit_author_name
_audit_author_address
'Hai Huang'
;Changzhou University
China
;
_audit_update_record             
;
2024-07-06 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-04-22
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 Cl N2 O6'
_chemical_formula_sum            'C18 H19 Cl N2 O6'
_chemical_formula_weight         394.80
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   8.8928(3)
_cell_length_b                   20.9134(8)
_cell_length_c                   10.5213(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4580(10)
_cell_angle_gamma                90
_cell_volume                     1917.74(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      59.297
_cell_measurement_theta_min      3.678
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1102 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.9235.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0490
_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       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30014
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        58.000
_diffrn_reflns_theta_max         59.305
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker MetalJet D2+ with PHOTON detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   GaK\a
_diffrn_source_current           3.57
_diffrn_source_power             0.24936449999999996
_diffrn_source_type              'excillum MetalJet D2+ Gallium'
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                7720
_reflns_number_total             8402
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 3303 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         8402
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.143
_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)+(0.0547P)²+1.5348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(Cl1A) \\sim Ueq:
with sigma of 0.003 and sigma for terminal atoms of 0.003
3. Rigid body (RIGU) restrains
 Cl1A, C7A, C8A, C9A, C10A, C11A, C12A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C31(H31A,H31B), C21A(H21C,H21D), C31A(H31C,H31D)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), N2A(H2AB),
 C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C22A(H22D,H22E,H22F), C32A(H32D,
 H32E,H32F)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1A(H1A), O2A(H2AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.17809(14) 0.45164(5) 1.30509(11) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.7345(3) 0.36746(15) 1.1124(3) 0.0220(6) Uani 1 1 d . . . . .
H1 H 0.652638 0.386748 1.081166 0.033 Uiso 1 1 calc R U . . .
O2 O 1.2538(3) 0.36189(15) 1.0807(3) 0.0239(6) Uani 1 1 d . . . . .
H2 H 1.316991 0.384484 1.051098 0.036 Uiso 1 1 calc R U . . .
O3 O 0.6060(3) 0.32270(14) 0.7961(3) 0.0210(6) Uani 1 1 d . . . . .
O4 O 0.4094(3) 0.39359(14) 0.7565(3) 0.0188(6) Uani 1 1 d . . . . .
O5 O 0.4339(4) 0.54391(16) 0.9656(3) 0.0294(7) Uani 1 1 d . . . . .
O6 O 0.4839(3) 0.44488(15) 1.0480(3) 0.0229(6) Uani 1 1 d . . . . .
N1 N 0.6487(4) 0.42347(16) 0.8612(3) 0.0172(7) Uani 1 1 d . . . . .
N2 N 0.5930(4) 0.48341(16) 0.8853(3) 0.0176(7) Uani 1 1 d . . . . .
H2A H 0.617157 0.517632 0.844967 0.021 Uiso 1 1 calc R U . . .
C1 C 0.8056(4) 0.40845(19) 0.9181(4) 0.0163(8) Uani 1 1 d . . . . .
C2 C 0.8413(4) 0.38105(19) 1.0414(4) 0.0160(8) Uani 1 1 d . . . . .
C3 C 0.9945(4) 0.36691(18) 1.0961(4) 0.0160(7) Uani 1 1 d . . . . .
C4 C 1.1081(4) 0.37968(19) 1.0246(4) 0.0176(8) Uani 1 1 d . . . . .
C5 C 1.0724(4) 0.4074(2) 0.9028(4) 0.0201(8) Uani 1 1 d . . . . .
H5 H 1.150907 0.416245 0.855828 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9210(4) 0.4219(2) 0.8502(4) 0.0183(8) Uani 1 1 d . . . . .
H6 H 0.895640 0.441301 0.767008 0.022 Uiso 1 1 calc R U . . .
C7 C 1.0358(4) 0.33917(19) 1.2292(4) 0.0158(7) Uani 1 1 d . . . . .
C8 C 1.1248(5) 0.3729(2) 1.3313(4) 0.0219(8) Uani 1 1 d . . . . .
C9 C 1.1708(5) 0.3465(2) 1.4537(4) 0.0276(10) Uani 1 1 d . . . . .
H9 H 1.234556 0.369976 1.520895 0.033 Uiso 1 1 calc R U . . .
C10 C 1.1225(5) 0.2855(2) 1.4762(4) 0.0287(10) Uani 1 1 d . . . . .
H10 H 1.153893 0.266696 1.559503 0.034 Uiso 1 1 calc R U . . .
C11 C 1.0286(5) 0.2514(2) 1.3784(4) 0.0274(9) Uani 1 1 d . . . . .
H11 H 0.993111 0.210067 1.395306 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9867(4) 0.2779(2) 1.2561(4) 0.0205(8) Uani 1 1 d . . . . .
H12 H 0.923532 0.254157 1.189131 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5421(4) 0.3798(2) 0.7998(4) 0.0165(8) Uani 1 1 d . . . . .
C21 C 0.5034(5) 0.2712(2) 0.7393(5) 0.0257(9) Uani 1 1 d . . . . .
H21A H 0.564965 0.234610 0.718916 0.031 Uiso 1 1 calc R U . . .
H21B H 0.438452 0.286302 0.657235 0.031 Uiso 1 1 calc R U . . .
C22 C 0.4024(6) 0.2497(3) 0.8301(5) 0.0376(11) Uani 1 1 d . . . . .
H22A H 0.346497 0.211083 0.795408 0.056 Uiso 1 1 calc R U . . .
H22B H 0.329155 0.283627 0.838722 0.056 Uiso 1 1 calc R U . . .
H22C H 0.465936 0.240294 0.915338 0.056 Uiso 1 1 calc R U . . .
C30 C 0.5009(4) 0.4874(2) 0.9724(4) 0.0192(8) Uani 1 1 d . . . . .
C31 C 0.3446(7) 0.5588(3) 1.0641(6) 0.0428(14) Uani 1 1 d . . . . .
H31A H 0.411503 0.558662 1.151413 0.051 Uiso 1 1 calc R U . . .
H31B H 0.262587 0.526630 1.062625 0.051 Uiso 1 1 calc R U . . .
C32 C 0.2770(9) 0.6230(3) 1.0337(7) 0.0594(19) Uani 1 1 d . . . . .
H32A H 0.206143 0.621788 0.949519 0.089 Uiso 1 1 calc R U . . .
H32B H 0.358986 0.653883 1.030277 0.089 Uiso 1 1 calc R U . . .
H32C H 0.221242 0.635779 1.101070 0.089 Uiso 1 1 calc R U . . .
Cl1A Cl 0.08953(17) 0.75003(6) 0.30013(14) 0.0449(3) Uani 1 1 d . U . . .
O1A O 0.2530(3) 0.61324(14) 0.3590(3) 0.0213(6) Uani 1 1 d . . . . .
H1A H 0.332731 0.592577 0.390600 0.032 Uiso 1 1 calc R U . . .
O2A O -0.2710(3) 0.61555(19) 0.3733(4) 0.0436(10) Uani 1 1 d . . . . .
H2AA H -0.333930 0.595648 0.408414 0.065 Uiso 1 1 calc R U . . .
O3A O 0.3653(3) 0.66217(14) 0.6915(3) 0.0223(6) Uani 1 1 d . . . . .
O4A O 0.5677(3) 0.59415(14) 0.7260(3) 0.0198(6) Uani 1 1 d . . . . .
O5A O 0.5522(3) 0.44140(15) 0.5158(3) 0.0251(7) Uani 1 1 d . . . . .
O6A O 0.5046(3) 0.54128(14) 0.4337(3) 0.0199(6) Uani 1 1 d . . . . .
N1A N 0.3325(3) 0.56303(16) 0.6155(3) 0.0169(7) Uani 1 1 d . . . . .
N2A N 0.3928(3) 0.50340(16) 0.5946(3) 0.0151(6) Uani 1 1 d . . . . .
H2AB H 0.370583 0.469567 0.637122 0.018 Uiso 1 1 calc R U . . .
C1A C 0.1755(4) 0.57682(18) 0.5546(4) 0.0180(8) Uani 1 1 d . . . . .
C2A C 0.1434(4) 0.60143(19) 0.4289(4) 0.0179(8) Uani 1 1 d . . . . .
C3A C -0.0084(4) 0.6141(2) 0.3683(4) 0.0218(8) Uani 1 1 d . . . . .
C4A C -0.1251(5) 0.6018(2) 0.4364(5) 0.0263(10) Uani 1 1 d . . . . .
C5A C -0.0932(5) 0.5771(2) 0.5616(5) 0.0278(10) Uani 1 1 d . . . . .
H5A H -0.173802 0.568891 0.606680 0.033 Uiso 1 1 calc R U . . .
C6A C 0.0578(5) 0.5648(2) 0.6197(4) 0.0210(8) Uani 1 1 d . . . . .
H6A H 0.080747 0.547824 0.705115 0.025 Uiso 1 1 calc R U . . .
C7A C -0.0464(5) 0.6356(2) 0.2304(5) 0.0261(9) Uani 1 1 d . U . . .
C8A C -0.0094(5) 0.6957(2) 0.1888(5) 0.0280(9) Uani 1 1 d . U . . .
C9A C -0.0489(5) 0.7143(3) 0.0605(5) 0.0381(10) Uani 1 1 d . U . . .
H9A H -0.023342 0.755870 0.035264 0.046 Uiso 1 1 calc R U . . .
C10A C -0.1250(7) 0.6726(3) -0.0298(6) 0.0515(13) Uani 1 1 d . U . . .
H10A H -0.152898 0.685138 -0.118172 0.062 Uiso 1 1 calc R U . . .
C11A C -0.1610(7) 0.6126(4) 0.0075(6) 0.0604(16) Uani 1 1 d . U . . .
H11A H -0.212680 0.583388 -0.055489 0.072 Uiso 1 1 calc R U . . .
C12A C -0.1225(7) 0.5941(3) 0.1371(5) 0.0482(13) Uani 1 1 d . U . . .
H12A H -0.148764 0.552521 0.161605 0.058 Uiso 1 1 calc R U . . .
C20A C 0.4340(4) 0.6068(2) 0.6827(4) 0.0164(7) Uani 1 1 d . . . . .
C21A C 0.4642(5) 0.7132(2) 0.7605(5) 0.0273(10) Uani 1 1 d . . . . .
H21C H 0.531447 0.695064 0.838510 0.033 Uiso 1 1 calc R U . . .
H21D H 0.399261 0.746539 0.789357 0.033 Uiso 1 1 calc R U . . .
C22A C 0.5608(6) 0.7429(3) 0.6750(6) 0.0389(12) Uani 1 1 d . . . . .
H22D H 0.494386 0.760369 0.597272 0.058 Uiso 1 1 calc R U . . .
H22E H 0.628499 0.710304 0.649626 0.058 Uiso 1 1 calc R U . . .
H22F H 0.622956 0.777280 0.722118 0.058 Uiso 1 1 calc R U . . .
C30A C 0.4854(4) 0.4983(2) 0.5084(4) 0.0176(8) Uani 1 1 d . . . . .
C31A C 0.6361(6) 0.4251(3) 0.4131(5) 0.0387(12) Uani 1 1 d . . . . .
H31C H 0.689479 0.463379 0.388651 0.046 Uiso 1 1 calc R U . . .
H31D H 0.563892 0.409551 0.335292 0.046 Uiso 1 1 calc R U . . .
C32A C 0.7483(7) 0.3749(3) 0.4636(6) 0.0508(16) Uani 1 1 d . . . . .
H32D H 0.797037 0.359442 0.393686 0.076 Uiso 1 1 calc R U . . .
H32E H 0.695681 0.339323 0.497030 0.076 Uiso 1 1 calc R U . . .
H32F H 0.826668 0.392439 0.533685 0.076 Uiso 1 1 calc R U . . .


_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 C8 1.750(4) . ?
O1 H1 0.8400 . ?
O1 C2 1.349(5) . ?
O2 H2 0.8400 . ?
O2 C4 1.365(5) . ?
O3 C20 1.326(5) . ?
O3 C21 1.460(5) . ?
O4 C20 1.212(5) . ?
O5 C30 1.318(5) . ?
O5 C31 1.459(5) . ?
O6 C30 1.223(5) . ?
N1 N2 1.389(5) . ?
N1 C1 1.439(5) . ?
N1 C20 1.381(5) . ?
N2 H2A 0.8800 . ?
N2 C30 1.348(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.391(5) . ?
C2 C3 1.401(5) . ?
C3 C4 1.400(5) . ?
C3 C7 1.493(5) . ?
C4 C5 1.385(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(6) . ?
C7 C12 1.400(6) . ?
C8 C9 1.386(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(6) . ?
C12 H12 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.504(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.480(8) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Cl1A C8A 1.740(5) . ?
O1A H1A 0.8400 . ?
O1A C2A 1.356(5) . ?
O2A H2AA 0.8400 . ?
O2A C4A 1.365(5) . ?
O3A C20A 1.321(5) . ?
O3A C21A 1.479(5) . ?
O4A C20A 1.215(5) . ?
O5A C30A 1.326(5) . ?
O5A C31A 1.469(5) . ?
O6A C30A 1.228(5) . ?
N1A N2A 1.392(5) . ?
N1A C1A 1.445(5) . ?
N1A C20A 1.378(5) . ?
N2A H2AB 0.8800 . ?
N2A C30A 1.345(5) . ?
C1A C2A 1.394(6) . ?
C1A C6A 1.384(6) . ?
C2A C3A 1.398(5) . ?
C3A C4A 1.397(6) . ?
C3A C7A 1.493(6) . ?
C4A C5A 1.391(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.384(6) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.393(6) . ?
C7A C12A 1.382(7) . ?
C8A C9A 1.381(7) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.366(9) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.372(9) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.392(8) . ?
C12A H12A 0.9500 . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C21A C22A 1.497(7) . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C31A H31C 0.9900 . ?
C31A H31D 0.9900 . ?
C31A C32A 1.474(7) . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C20 O3 C21 116.0(3) . . ?
C30 O5 C31 117.1(4) . . ?
N2 N1 C1 118.2(3) . . ?
C20 N1 N2 116.5(3) . . ?
C20 N1 C1 124.7(3) . . ?
N1 N2 H2A 121.1 . . ?
C30 N2 N1 117.8(3) . . ?
C30 N2 H2A 121.1 . . ?
C2 C1 N1 119.9(3) . . ?
C6 C1 N1 119.7(3) . . ?
C6 C1 C2 120.4(3) . . ?
O1 C2 C1 123.0(3) . . ?
O1 C2 C3 117.5(4) . . ?
C1 C2 C3 119.4(4) . . ?
C2 C3 C7 120.4(3) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 C7 120.6(3) . . ?
O2 C4 C3 116.1(4) . . ?
O2 C4 C5 122.5(4) . . ?
C5 C4 C3 121.3(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C3 121.5(4) . . ?
C8 C7 C12 117.4(4) . . ?
C12 C7 C3 121.1(4) . . ?
C7 C8 Cl1 119.0(3) . . ?
C9 C8 Cl1 118.8(3) . . ?
C9 C8 C7 122.1(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
O3 C20 N1 110.5(3) . . ?
O4 C20 O3 126.5(4) . . ?
O4 C20 N1 123.0(4) . . ?
O3 C21 H21A 109.4 . . ?
O3 C21 H21B 109.4 . . ?
O3 C21 C22 111.4(4) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C30 N2 110.4(3) . . ?
O6 C30 O5 125.1(4) . . ?
O6 C30 N2 124.5(4) . . ?
O5 C31 H31A 110.3 . . ?
O5 C31 H31B 110.3 . . ?
O5 C31 C32 107.1(4) . . ?
H31A C31 H31B 108.5 . . ?
C32 C31 H31A 110.3 . . ?
C32 C31 H31B 110.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C2A O1A H1A 109.5 . . ?
C4A O2A H2AA 109.5 . . ?
C20A O3A C21A 115.4(3) . . ?
C30A O5A C31A 116.9(3) . . ?
N2A N1A C1A 118.5(3) . . ?
C20A N1A N2A 116.3(3) . . ?
C20A N1A C1A 124.9(3) . . ?
N1A N2A H2AB 120.5 . . ?
C30A N2A N1A 118.9(3) . . ?
C30A N2A H2AB 120.5 . . ?
C2A C1A N1A 119.5(4) . . ?
C6A C1A N1A 120.2(4) . . ?
C6A C1A C2A 120.2(4) . . ?
O1A C2A C1A 123.2(3) . . ?
O1A C2A C3A 116.9(4) . . ?
C1A C2A C3A 120.0(4) . . ?
C2A C3A C7A 120.8(4) . . ?
C4A C3A C2A 118.7(4) . . ?
C4A C3A C7A 120.4(4) . . ?
O2A C4A C3A 116.3(4) . . ?
O2A C4A C5A 122.3(4) . . ?
C5A C4A C3A 121.4(4) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A C4A 119.0(4) . . ?
C6A C5A H5A 120.5 . . ?
C1A C6A C5A 120.7(4) . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C8A C7A C3A 123.8(4) . . ?
C12A C7A C3A 119.1(4) . . ?
C12A C7A C8A 117.1(4) . . ?
C7A C8A Cl1A 119.8(4) . . ?
C9A C8A Cl1A 118.1(4) . . ?
C9A C8A C7A 122.1(5) . . ?
C8A C9A H9A 120.1 . . ?
C10A C9A C8A 119.7(5) . . ?
C10A C9A H9A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C9A C10A C11A 119.7(5) . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A H11A 119.7 . . ?
C10A C11A C12A 120.5(6) . . ?
C12A C11A H11A 119.7 . . ?
C7A C12A C11A 120.8(5) . . ?
C7A C12A H12A 119.6 . . ?
C11A C12A H12A 119.6 . . ?
O3A C20A N1A 110.7(3) . . ?
O4A C20A O3A 126.6(4) . . ?
O4A C20A N1A 122.7(4) . . ?
O3A C21A H21C 109.4 . . ?
O3A C21A H21D 109.4 . . ?
O3A C21A C22A 111.1(4) . . ?
H21C C21A H21D 108.0 . . ?
C22A C21A H21C 109.4 . . ?
C22A C21A H21D 109.4 . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O5A C30A N2A 111.0(3) . . ?
O6A C30A O5A 125.2(4) . . ?
O6A C30A N2A 123.8(4) . . ?
O5A C31A H31C 110.1 . . ?
O5A C31A H31D 110.1 . . ?
O5A C31A C32A 107.8(4) . . ?
H31C C31A H31D 108.5 . . ?
C32A C31A H31C 110.1 . . ?
C32A C31A H31D 110.1 . . ?
C31A C32A H32D 109.5 . . ?
C31A C32A H32E 109.5 . . ?
C31A C32A H32F 109.5 . . ?
H32D C32A H32E 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 O6 0.84 1.91 2.729(4) 165.1 . yes
O2 H2 O6 0.84 1.95 2.756(4) 159.4 1_655 yes
O1A H1A O6A 0.84 1.85 2.681(4) 170.7 . yes
O2A H2AA O6A 0.84 1.89 2.703(4) 161.9 1_455 yes

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
Cl1 C8 C9 C10 176.8(3) . . . . ?
O1 C2 C3 C4 179.2(3) . . . . ?
O1 C2 C3 C7 -1.3(6) . . . . ?
O2 C4 C5 C6 177.6(4) . . . . ?
N1 N2 C30 O5 -167.5(3) . . . . ?
N1 N2 C30 O6 13.4(6) . . . . ?
N1 C1 C2 O1 0.0(6) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
N1 C1 C6 C5 -179.5(4) . . . . ?
N2 N1 C1 C2 89.2(4) . . . . ?
N2 N1 C1 C6 -90.2(4) . . . . ?
N2 N1 C20 O3 -172.7(3) . . . . ?
N2 N1 C20 O4 7.3(5) . . . . ?
C1 N1 N2 C30 -103.4(4) . . . . ?
C1 N1 C20 O3 -2.4(5) . . . . ?
C1 N1 C20 O4 177.6(4) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C7 178.4(4) . . . . ?
C2 C1 C6 C5 1.2(6) . . . . ?
C2 C3 C4 O2 -176.9(3) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C2 C3 C7 C8 -114.3(4) . . . . ?
C2 C3 C7 C12 65.9(5) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C7 C8 Cl1 4.4(5) . . . . ?
C3 C7 C8 C9 -176.5(4) . . . . ?
C3 C7 C12 C11 178.1(4) . . . . ?
C4 C3 C7 C8 65.2(5) . . . . ?
C4 C3 C7 C12 -114.7(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C6 C1 C2 O1 179.4(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C7 C3 C4 O2 3.7(6) . . . . ?
C7 C3 C4 C5 -177.8(4) . . . . ?
C7 C8 C9 C10 -2.3(6) . . . . ?
C8 C7 C12 C11 -1.7(6) . . . . ?
C8 C9 C10 C11 -0.5(7) . . . . ?
C9 C10 C11 C12 2.0(7) . . . . ?
C10 C11 C12 C7 -0.9(6) . . . . ?
C12 C7 C8 Cl1 -175.8(3) . . . . ?
C12 C7 C8 C9 3.3(6) . . . . ?
C20 O3 C21 C22 -74.6(5) . . . . ?
C20 N1 N2 C30 67.6(4) . . . . ?
C20 N1 C1 C2 -81.0(5) . . . . ?
C20 N1 C1 C6 99.6(5) . . . . ?
C21 O3 C20 O4 -3.0(6) . . . . ?
C21 O3 C20 N1 177.0(3) . . . . ?
C30 O5 C31 C32 -178.0(5) . . . . ?
C31 O5 C30 O6 6.2(7) . . . . ?
C31 O5 C30 N2 -172.8(4) . . . . ?
Cl1A C8A C9A C10A 179.2(4) . . . . ?
O1A C2A C3A C4A 179.2(4) . . . . ?
O1A C2A C3A C7A 3.8(6) . . . . ?
O2A C4A C5A C6A -179.6(5) . . . . ?
N1A N2A C30A O5A 169.7(3) . . . . ?
N1A N2A C30A O6A -10.1(6) . . . . ?
N1A C1A C2A O1A 0.2(6) . . . . ?
N1A C1A C2A C3A 179.1(4) . . . . ?
N1A C1A C6A C5A -179.3(4) . . . . ?
N2A N1A C1A C2A -86.9(4) . . . . ?
N2A N1A C1A C6A 92.1(5) . . . . ?
N2A N1A C20A O3A 177.3(3) . . . . ?
N2A N1A C20A O4A -2.5(5) . . . . ?
C1A N1A N2A C30A 101.5(4) . . . . ?
C1A N1A C20A O3A 4.2(5) . . . . ?
C1A N1A C20A O4A -175.5(4) . . . . ?
C1A C2A C3A C4A 0.3(6) . . . . ?
C1A C2A C3A C7A -175.2(4) . . . . ?
C2A C1A C6A C5A -0.3(6) . . . . ?
C2A C3A C4A O2A 179.4(4) . . . . ?
C2A C3A C4A C5A -0.4(7) . . . . ?
C2A C3A C7A C8A -70.6(6) . . . . ?
C2A C3A C7A C12A 109.3(5) . . . . ?
C3A C4A C5A C6A 0.2(7) . . . . ?
C3A C7A C8A Cl1A 1.1(6) . . . . ?
C3A C7A C8A C9A -178.9(4) . . . . ?
C3A C7A C12A C11A 179.5(6) . . . . ?
C4A C3A C7A C8A 114.0(5) . . . . ?
C4A C3A C7A C12A -66.1(7) . . . . ?
C4A C5A C6A C1A 0.1(7) . . . . ?
C6A C1A C2A O1A -178.8(4) . . . . ?
C6A C1A C2A C3A 0.1(6) . . . . ?
C7A C3A C4A O2A -5.1(7) . . . . ?
C7A C3A C4A C5A 175.1(4) . . . . ?
C7A C8A C9A C10A -0.9(7) . . . . ?
C8A C7A C12A C11A -0.6(9) . . . . ?
C8A C9A C10A C11A -0.2(9) . . . . ?
C9A C10A C11A C12A 0.9(10) . . . . ?
C10A C11A C12A C7A -0.4(11) . . . . ?
C12A C7A C8A Cl1A -178.8(4) . . . . ?
C12A C7A C8A C9A 1.3(7) . . . . ?
C20A O3A C21A C22A 78.9(5) . . . . ?
C20A N1A N2A C30A -72.0(4) . . . . ?
C20A N1A C1A C2A 86.0(5) . . . . ?
C20A N1A C1A C6A -95.0(5) . . . . ?
C21A O3A C20A O4A 0.5(6) . . . . ?
C21A O3A C20A N1A -179.2(3) . . . . ?
C30A O5A C31A C32A 157.9(5) . . . . ?
C31A O5A C30A O6A -10.2(6) . . . . ?
C31A O5A C30A N2A 170.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
