# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_03482
_database_code_depnum_ccdc_archive 'CCDC 2160961'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CF-paracloro
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl N O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         341.74
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   10.609(2)
_cell_length_b                   10.874(2)
_cell_length_c                   13.846(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.908(8)
_cell_angle_gamma                90
_cell_volume                     1593.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      3.0001
_cell_measurement_theta_max      20.6271
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.034
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            50886
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5830
_reflns_number_gt                4516
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1119
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_number_reflns         5830
_refine_ls_number_parameters     425
_refine_ls_number_restraints     7
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.2533P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1753 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.41174(13) 0.41092(15) 0.13965(9) 0.0777(4) Uani d . . . 1 . .
C C1 0.3867(4) 0.4856(5) 0.2488(3) 0.0535(11) Uani d . . . 1 . .
C C2 0.3000(4) 0.5796(5) 0.2520(4) 0.0634(13) Uani d . . . 1 . .
H H2 0.252163 0.602327 0.196093 0.076000 Uiso calc U . R 1 . .
C C3 0.2843(4) 0.6395(5) 0.3371(4) 0.0639(14) Uani d . . . 1 . .
H H3 0.224664 0.701911 0.339259 0.077000 Uiso calc U . R 1 . .
C C4 0.3579(4) 0.6069(4) 0.4211(4) 0.0539(11) Uani d . . . 1 . .
C C5 0.4432(4) 0.5102(4) 0.4187(3) 0.0445(10) Uani d . . . 1 . .
C C6 0.4571(4) 0.4507(4) 0.3313(3) 0.0452(10) Uani d . . . 1 . .
H H6 0.514668 0.386473 0.328508 0.054000 Uiso calc U . R 1 . .
C C7 0.5244(4) 0.4670(4) 0.5061(3) 0.0440(10) Uani d . . D 1 . .
H H7 0.536515 0.378025 0.500536 0.053000 Uiso calc U . R 1 . .
C C8 0.6554(3) 0.5277(4) 0.5235(3) 0.0382(9) Uani d . . . 1 . .
H H8 0.718934 0.483091 0.489170 0.046000 Uiso calc U . R 1 . .
C C9 0.6582(4) 0.6629(4) 0.5001(3) 0.0432(10) Uani d . . . 1 . .
C C10 0.7252(4) 0.6529(4) 0.6614(3) 0.0418(9) Uani d . . . 1 . .
H H10 0.686181 0.678937 0.720175 0.050000 Uiso calc U . R 1 . .
C C11 0.6856(3) 0.5214(4) 0.6335(3) 0.0373(8) Uani d . . . 1 . .
H H11 0.755854 0.464523 0.648566 0.045000 Uiso calc U . R 1 . .
C C12 0.5638(4) 0.4723(4) 0.6753(3) 0.0421(9) Uani d . . D 1 . .
H H12 0.573142 0.383864 0.687342 0.051000 Uiso calc U . R 1 . .
C C13 0.9037(6) 0.7756(5) 0.7052(4) 0.0798(17) Uani d . . . 1 . .
H H13A 0.992727 0.778838 0.696988 0.120000 Uiso calc U . R 1 . .
H H13B 0.889178 0.788338 0.772183 0.120000 Uiso calc U . R 1 . .
H H13C 0.861509 0.838721 0.666789 0.120000 Uiso calc U . R 1 . .
C C14 0.5308(4) 0.5352(4) 0.7677(3) 0.0430(9) Uani d . . . 1 . .
C C15 0.5936(5) 0.5523(6) 0.9339(3) 0.0684(14) Uani d . . . 1 . .
H H15A 0.662352 0.529661 0.979097 0.103000 Uiso calc U . R 1 . .
H H15B 0.516082 0.519992 0.955392 0.103000 Uiso calc U . R 1 . .
H H15C 0.588153 0.640337 0.929982 0.103000 Uiso calc U . R 1 . .
N N1 0.4654(3) 0.4917(4) 0.5974(2) 0.0498(9) Uani d . . D 1 . .
H H1N 0.397(3) 0.447(4) 0.603(3) 0.060000 Uiso d U . D 1 . .
O O1 0.3428(3) 0.6719(3) 0.5036(3) 0.0711(10) Uani d . . . 1 . .
H H1O 0.390645 0.644813 0.547538 0.107000 Uiso calc U . R 1 . .
O O2 0.6844(3) 0.7300(3) 0.5807(2) 0.0485(7) Uani d . . . 1 . .
O O3 0.6398(3) 0.7123(3) 0.4223(2) 0.0589(8) Uani d . . . 1 . .
O O4 0.8549(3) 0.6566(3) 0.6747(2) 0.0601(8) Uani d . . . 1 . .
O O5 0.6151(3) 0.5025(3) 0.8392(2) 0.0546(8) Uani d . . . 1 . .
Cl Cl2 -0.1725(2) 0.4993(2) 1.29798(13) 0.1212(8) Uani d . . . 1 . .
C C16 -0.1645(5) 0.4281(6) 1.1860(4) 0.0734(16) Uani d . . . 1 . .
C C17 -0.2382(5) 0.3259(6) 1.1612(5) 0.0802(19) Uani d . . . 1 . .
H H17 -0.292276 0.293291 1.204706 0.096000 Uiso calc U . R 1 . .
C C18 -0.2301(5) 0.2743(5) 1.0726(5) 0.0737(16) Uani d . . . 1 . .
H H18 -0.279747 0.206107 1.055665 0.088000 Uiso calc U . R 1 . .
C C19 -0.1498(4) 0.3208(4) 1.0066(4) 0.0565(12) Uani d . . . 1 . .
C C20 -0.0759(4) 0.4243(4) 1.0307(3) 0.0453(10) Uani d . . . 1 . .
C C21 -0.0846(4) 0.4779(4) 1.1206(4) 0.0564(12) Uani d . . . 1 . .
H H21 -0.036859 0.547342 1.137358 0.068000 Uiso calc U . R 1 . .
C C22 0.0103(4) 0.4827(4) 0.9614(3) 0.0432(9) Uani d . . D 1 . .
H H22 0.015125 0.571149 0.974674 0.052000 Uiso calc U . R 1 . .
C C23 0.1467(3) 0.4310(4) 0.9615(3) 0.0393(9) Uani d . . . 1 . .
H H23 0.203337 0.476021 1.007829 0.047000 Uiso calc U . R 1 . .
C C24 0.1564(4) 0.2944(4) 0.9799(3) 0.0437(10) Uani d . . . 1 . .
C C25 0.2415(4) 0.3229(4) 0.8333(3) 0.0456(10) Uani d . . . 1 . .
H H25 0.216322 0.299410 0.766450 0.055000 Uiso calc U . R 1 . .
C C26 0.1875(3) 0.4483(3) 0.8577(3) 0.0395(9) Uani d . . . 1 . .
H H26 0.253250 0.511556 0.856730 0.047000 Uiso calc U . R 1 . .
C C27 0.0657(4) 0.4922(4) 0.7995(3) 0.0449(9) Uani d . . D 1 . .
H H27 0.070399 0.581458 0.790767 0.054000 Uiso calc U . R 1 . .
C C28 0.4375(5) 0.2203(5) 0.8270(4) 0.0647(13) Uani d . . . 1 . .
H H28A 0.526278 0.231747 0.842474 0.097000 Uiso calc U . R 1 . .
H H28B 0.423165 0.201061 0.759472 0.097000 Uiso calc U . R 1 . .
H H28C 0.407322 0.154036 0.864983 0.097000 Uiso calc U . R 1 . .
C C29 0.0414(4) 0.4325(5) 0.7017(3) 0.0565(12) Uani d . . . 1 . .
C C30 0.0978(7) 0.4332(11) 0.5406(4) 0.127(3) Uani d . . . 1 . .
H H30A 0.155834 0.472834 0.500365 0.190000 Uiso calc U . R 1 . .
H H30B 0.012749 0.451163 0.516655 0.190000 Uiso calc U . R 1 . .
H H30C 0.111284 0.345953 0.539632 0.190000 Uiso calc U . R 1 . .
N N2 -0.0370(3) 0.4647(3) 0.8602(3) 0.0509(9) Uani d . . D 1 . .
H H2N -0.103(3) 0.515(4) 0.847(3) 0.061000 Uiso d U . D 1 . .
O O6 0.4451(3) 0.6045(3) 0.7755(2) 0.0592(8) Uani d . . . 1 . .
O O7 -0.1448(4) 0.2619(3) 0.9206(3) 0.0757(10) Uani d . . . 1 . .
H H7O -0.094425 0.297074 0.887690 0.091000 Uiso calc U . R 1 . .
O O8 0.1953(3) 0.2364(3) 0.9008(2) 0.0570(8) Uani d . . . 1 . .
O O9 0.1351(3) 0.2393(3) 1.0515(3) 0.0578(8) Uani d . . . 1 . .
O O10 0.3713(3) 0.3309(3) 0.8479(2) 0.0561(8) Uani d . . . 1 . .
O O11 0.1184(3) 0.4784(4) 0.6395(2) 0.0827(12) Uani d . . . 1 . .
O O12 -0.0352(3) 0.3561(4) 0.6820(3) 0.0791(11) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.752(5) ?
C1 C6 . 1.375(6) ?
C1 C2 . 1.377(7) ?
C2 C3 . 1.366(8) ?
C3 C4 . 1.402(7) ?
C4 O1 . 1.362(6) ?
C4 C5 . 1.389(6) ?
C5 C6 . 1.390(6) ?
C5 C7 . 1.512(6) ?
C7 N1 . 1.473(5) ?
C7 C8 . 1.542(5) ?
C8 C9 . 1.506(6) ?
C8 C11 . 1.536(6) ?
C9 O3 . 1.207(5) ?
C9 O2 . 1.347(5) ?
C10 O4 . 1.376(5) ?
C10 O2 . 1.439(5) ?
C10 C11 . 1.532(6) ?
C11 C12 . 1.547(5) ?
C12 N1 . 1.464(5) ?
C12 C14 . 1.513(6) ?
C13 O4 . 1.446(6) ?
C14 O6 . 1.191(5) ?
C14 O5 . 1.336(5) ?
C15 O5 . 1.452(5) ?
Cl2 C16 . 1.740(6) ?
C16 C17 . 1.388(9) ?
C16 C21 . 1.392(7) ?
C17 C18 . 1.358(9) ?
C18 C19 . 1.387(7) ?
C19 O7 . 1.356(6) ?
C19 C20 . 1.399(7) ?
C20 C21 . 1.382(6) ?
C20 C22 . 1.511(6) ?
C22 N2 . 1.469(6) ?
C22 C23 . 1.552(5) ?
C23 C24 . 1.509(6) ?
C23 C26 . 1.541(6) ?
C24 O9 . 1.193(5) ?
C24 O8 . 1.354(5) ?
C25 O10 . 1.381(5) ?
C25 O8 . 1.435(5) ?
C25 C26 . 1.526(6) ?
C26 C27 . 1.551(5) ?
C27 N2 . 1.452(5) ?
C27 C29 . 1.508(7) ?
C28 O10 . 1.432(5) ?
C29 O12 . 1.181(6) ?
C29 O11 . 1.324(6) ?
C30 O11 . 1.457(7) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 120.3(5) ?
C6 C1 Cl1 . . 118.8(4) ?
C2 C1 Cl1 . . 120.8(4) ?
C3 C2 C1 . . 120.1(4) ?
C2 C3 C4 . . 120.1(5) ?
O1 C4 C5 . . 121.8(4) ?
O1 C4 C3 . . 118.3(4) ?
C5 C4 C3 . . 119.9(5) ?
C4 C5 C6 . . 118.8(4) ?
C4 C5 C7 . . 123.5(4) ?
C6 C5 C7 . . 117.6(4) ?
C1 C6 C5 . . 120.7(4) ?
N1 C7 C5 . . 112.2(3) ?
N1 C7 C8 . . 102.7(3) ?
C5 C7 C8 . . 116.8(3) ?
C9 C8 C11 . . 104.5(3) ?
C9 C8 C7 . . 114.5(3) ?
C11 C8 C7 . . 105.1(3) ?
O3 C9 O2 . . 120.7(4) ?
O3 C9 C8 . . 128.4(4) ?
O2 C9 C8 . . 110.9(4) ?
O4 C10 O2 . . 109.4(3) ?
O4 C10 C11 . . 108.4(3) ?
O2 C10 C11 . . 106.6(3) ?
C10 C11 C8 . . 104.1(3) ?
C10 C11 C12 . . 116.7(3) ?
C8 C11 C12 . . 105.2(3) ?
N1 C12 C14 . . 111.3(3) ?
N1 C12 C11 . . 104.3(3) ?
C14 C12 C11 . . 114.1(3) ?
O6 C14 O5 . . 125.3(4) ?
O6 C14 C12 . . 125.8(4) ?
O5 C14 C12 . . 108.9(3) ?
C12 N1 C7 . . 106.3(3) ?
C9 O2 C10 . . 111.2(3) ?
C10 O4 C13 . . 113.6(4) ?
C14 O5 C15 . . 115.6(4) ?
C17 C16 C21 . . 120.5(5) ?
C17 C16 Cl2 . . 121.1(4) ?
C21 C16 Cl2 . . 118.4(5) ?
C18 C17 C16 . . 119.1(5) ?
C17 C18 C19 . . 121.6(5) ?
O7 C19 C18 . . 118.0(5) ?
O7 C19 C20 . . 122.4(4) ?
C18 C19 C20 . . 119.7(5) ?
C21 C20 C19 . . 118.9(4) ?
C21 C20 C22 . . 118.3(4) ?
C19 C20 C22 . . 122.7(4) ?
C20 C21 C16 . . 120.2(5) ?
N2 C22 C20 . . 111.6(3) ?
N2 C22 C23 . . 102.2(3) ?
C20 C22 C23 . . 116.9(3) ?
C24 C23 C26 . . 105.0(3) ?
C24 C23 C22 . . 114.2(3) ?
C26 C23 C22 . . 106.0(3) ?
O9 C24 O8 . . 121.6(4) ?
O9 C24 C23 . . 128.3(4) ?
O8 C24 C23 . . 110.0(4) ?
O10 C25 O8 . . 109.1(3) ?
O10 C25 C26 . . 107.3(3) ?
O8 C25 C26 . . 106.9(3) ?
C25 C26 C23 . . 103.4(3) ?
C25 C26 C27 . . 118.1(3) ?
C23 C26 C27 . . 104.2(3) ?
N2 C27 C29 . . 110.0(4) ?
N2 C27 C26 . . 105.5(3) ?
C29 C27 C26 . . 114.8(3) ?
O12 C29 O11 . . 124.0(5) ?
O12 C29 C27 . . 125.6(4) ?
O11 C29 C27 . . 110.3(4) ?
C27 N2 C22 . . 107.7(3) ?
C24 O8 C25 . . 111.0(3) ?
C25 O10 C28 . . 114.5(4) ?
C29 O11 C30 . . 115.2(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.6(7) ?
Cl1 C1 C2 C3 . . . . -178.0(4) ?
C1 C2 C3 C4 . . . . 1.1(7) ?
C2 C3 C4 O1 . . . . 177.5(4) ?
C2 C3 C4 C5 . . . . -2.7(7) ?
O1 C4 C5 C6 . . . . -177.7(4) ?
C3 C4 C5 C6 . . . . 2.5(6) ?
O1 C4 C5 C7 . . . . 1.1(6) ?
C3 C4 C5 C7 . . . . -178.7(4) ?
C2 C1 C6 C5 . . . . -0.7(6) ?
Cl1 C1 C6 C5 . . . . 177.9(3) ?
C4 C5 C6 C1 . . . . -0.8(6) ?
C7 C5 C6 C1 . . . . -179.7(4) ?
C4 C5 C7 N1 . . . . 27.7(5) ?
C6 C5 C7 N1 . . . . -153.5(3) ?
C4 C5 C7 C8 . . . . -90.4(5) ?
C6 C5 C7 C8 . . . . 88.4(5) ?
N1 C7 C8 C9 . . . . -85.6(4) ?
C5 C7 C8 C9 . . . . 37.6(5) ?
N1 C7 C8 C11 . . . . 28.6(4) ?
C5 C7 C8 C11 . . . . 151.7(3) ?
C11 C8 C9 O3 . . . . -180.0(4) ?
C7 C8 C9 O3 . . . . -65.5(6) ?
C11 C8 C9 O2 . . . . -0.4(4) ?
C7 C8 C9 O2 . . . . 114.1(4) ?
O4 C10 C11 C8 . . . . -102.2(3) ?
O2 C10 C11 C8 . . . . 15.4(4) ?
O4 C10 C11 C12 . . . . 142.4(3) ?
O2 C10 C11 C12 . . . . -100.0(4) ?
C9 C8 C11 C10 . . . . -9.2(4) ?
C7 C8 C11 C10 . . . . -130.1(3) ?
C9 C8 C11 C12 . . . . 114.1(3) ?
C7 C8 C11 C12 . . . . -6.9(4) ?
C10 C11 C12 N1 . . . . 97.3(4) ?
C8 C11 C12 N1 . . . . -17.6(4) ?
C10 C11 C12 C14 . . . . -24.3(5) ?
C8 C11 C12 C14 . . . . -139.1(3) ?
N1 C12 C14 O6 . . . . -8.8(6) ?
C11 C12 C14 O6 . . . . 108.9(5) ?
N1 C12 C14 O5 . . . . 172.4(3) ?
C11 C12 C14 O5 . . . . -69.9(4) ?
C14 C12 N1 C7 . . . . 160.4(3) ?
C11 C12 N1 C7 . . . . 37.0(4) ?
C5 C7 N1 C12 . . . . -167.3(3) ?
C8 C7 N1 C12 . . . . -41.2(4) ?
O3 C9 O2 C10 . . . . -169.5(4) ?
C8 C9 O2 C10 . . . . 10.9(4) ?
O4 C10 O2 C9 . . . . 100.2(4) ?
C11 C10 O2 C9 . . . . -16.8(4) ?
O2 C10 O4 C13 . . . . 66.5(4) ?
C11 C10 O4 C13 . . . . -177.7(4) ?
O6 C14 O5 C15 . . . . 3.2(6) ?
C12 C14 O5 C15 . . . . -178.0(4) ?
C21 C16 C17 C18 . . . . 0.7(7) ?
Cl2 C16 C17 C18 . . . . 179.1(4) ?
C16 C17 C18 C19 . . . . 0.3(8) ?
C17 C18 C19 O7 . . . . 178.2(5) ?
C17 C18 C19 C20 . . . . -0.8(7) ?
O7 C19 C20 C21 . . . . -178.8(4) ?
C18 C19 C20 C21 . . . . 0.2(6) ?
O7 C19 C20 C22 . . . . 3.2(6) ?
C18 C19 C20 C22 . . . . -177.8(4) ?
C19 C20 C21 C16 . . . . 0.8(6) ?
C22 C20 C21 C16 . . . . 179.0(4) ?
C17 C16 C21 C20 . . . . -1.3(7) ?
Cl2 C16 C21 C20 . . . . -179.7(3) ?
C21 C20 C22 N2 . . . . -148.9(4) ?
C19 C20 C22 N2 . . . . 29.2(5) ?
C21 C20 C22 C23 . . . . 94.1(5) ?
C19 C20 C22 C23 . . . . -87.8(5) ?
N2 C22 C23 C24 . . . . -87.4(4) ?
C20 C22 C23 C24 . . . . 34.7(5) ?
N2 C22 C23 C26 . . . . 27.7(4) ?
C20 C22 C23 C26 . . . . 149.8(4) ?
C26 C23 C24 O9 . . . . 179.2(4) ?
C22 C23 C24 O9 . . . . -65.2(5) ?
C26 C23 C24 O8 . . . . -0.6(4) ?
C22 C23 C24 O8 . . . . 115.1(4) ?
O10 C25 C26 C23 . . . . -98.9(3) ?
O8 C25 C26 C23 . . . . 18.0(4) ?
O10 C25 C26 C27 . . . . 146.7(3) ?
O8 C25 C26 C27 . . . . -96.3(4) ?
C24 C23 C26 C25 . . . . -10.7(4) ?
C22 C23 C26 C25 . . . . -131.9(3) ?
C24 C23 C26 C27 . . . . 113.4(3) ?
C22 C23 C26 C27 . . . . -7.8(4) ?
C25 C26 C27 N2 . . . . 98.5(4) ?
C23 C26 C27 N2 . . . . -15.4(4) ?
C25 C26 C27 C29 . . . . -22.8(5) ?
C23 C26 C27 C29 . . . . -136.7(4) ?
N2 C27 C29 O12 . . . . -13.5(7) ?
C26 C27 C29 O12 . . . . 105.3(5) ?
N2 C27 C29 O11 . . . . 166.2(4) ?
C26 C27 C29 O11 . . . . -75.0(5) ?
C29 C27 N2 C22 . . . . 159.1(3) ?
C26 C27 N2 C22 . . . . 34.7(4) ?
C20 C22 N2 C27 . . . . -164.5(3) ?
C23 C22 N2 C27 . . . . -38.9(4) ?
O9 C24 O8 C25 . . . . -167.0(4) ?
C23 C24 O8 C25 . . . . 12.8(4) ?
O10 C25 O8 C24 . . . . 95.9(4) ?
C26 C25 O8 C24 . . . . -19.8(4) ?
O8 C25 O10 C28 . . . . 65.2(4) ?
C26 C25 O10 C28 . . . . -179.3(4) ?
O12 C29 O11 C30 . . . . 3.6(8) ?
C27 C29 O11 C30 . . . . -176.1(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O7 2_556 0.930000 2.580000 3.438(6) 153.200000 ?
C3 H3 O12 2_556 0.930000 2.620000 3.537(6) 169.300000 ?
C7 H7 O1 2_646 0.980000 2.580000 3.511(5) 157.800000 ?
C8 H8 Cl2 1_654 0.980000 2.960000 3.737(4) 136.600000 ?
C11 H11 O12 1_655 0.980000 2.530000 3.491(5) 168.200000 ?
C13 H13B O9 2_657 0.960000 2.530000 3.444(7) 159.300000 ?
N1 H1N O3 2_646 0.89(2) 2.60(4) 3.242(5) 130.(4) ?
O1 H1O N1 . 0.820000 1.950000 2.643(5) 141.800000 ?
C17 H17 O6 2_547 0.930000 2.640000 3.413(7) 140.700000 ?
C22 H22 O9 2_557 0.980000 2.440000 3.188(5) 133.100000 ?
C23 H23 Cl1 1_556 0.980000 2.860000 3.619(4) 135.000000 ?
C26 H26 O6 . 0.980000 2.600000 3.475(5) 149.200000 ?
C28 H28B O3 2_646 0.960000 2.560000 3.495(6) 163.600000 ?
O7 H7O N2 . 0.820000 1.970000 2.646(5) 139.600000 ?

