# 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_03432def
_database_code_depnum_ccdc_archive 'CCDC 2173555'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ccgnme
_chemical_formula_moiety         ?
_chemical_formula_sum            'C82 H82 F6 N8 O12 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         1613.79
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   17.233(3)
_cell_length_b                   6.965(2)
_cell_length_c                   18.586(4)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     2230.8(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3713
_cell_measurement_theta_min      3.3398
_cell_measurement_theta_max      21.5382
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.134
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844

_exptl_absorpt_coefficient_mu    0.178
_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  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(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            10595
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3936
_reflns_number_gt                2971
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1976
_refine_ls_R_factor_gt           0.1674
_refine_ls_wR_factor_gt          0.4126
_refine_ls_wR_factor_ref         0.4383
_refine_ls_goodness_of_fit_ref   1.872
_refine_ls_restrained_S_all      1.873
_refine_ls_number_reflns         3936
_refine_ls_number_parameters     260
_refine_ls_number_restraints     13
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.680
_refine_diff_density_min         -0.733
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.11(4)
_refine_ls_abs_structure_details 
;

Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_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
C C1 0.4555(7) 0.6112(19) 0.5117(6) 0.069(3) Uani d . . . 1 . .
C C2 0.4576(8) 0.556(3) 0.4387(8) 0.097(5) Uani d . . . 1 . .
H H2 0.439912 0.432620 0.425841 0.116000 Uiso calc U . R 1 . .
C C3 0.4844(14) 0.674(5) 0.3865(9) 0.136(9) Uani d . . . 1 . .
C C4 0.5105(14) 0.861(4) 0.4057(9) 0.121(6) Uani d . . . 1 . .
H H4 0.532741 0.941237 0.370648 0.145000 Uiso calc U . R 1 . .
C C5 0.5031(9) 0.927(3) 0.4773(8) 0.098(5) Uani d . . . 1 . .
H H5 0.515567 1.054062 0.489544 0.118000 Uiso calc U . R 1 . .
C C6 0.4770(6) 0.7980(17) 0.5293(6) 0.065(3) Uani d . . . 1 . .
C C7 0.4223(8) 0.4913(16) 0.5684(8) 0.080(4) Uani d . . D 1 . .
H H7 0.464899 0.454390 0.601362 0.096000 Uiso calc U . R 1 . .
C C8 0.3643(6) 0.6122(18) 0.6116(7) 0.065(3) Uani d . . . 1 . .
H H8 0.326519 0.672725 0.578455 0.078000 Uiso calc U . R 1 . .
C C9 0.4093(7) 0.7664(16) 0.6512(7) 0.067(3) Uani d . . . 1 . .
H H9A 0.373320 0.864749 0.668709 0.080000 Uiso calc U . R 1 . .
H H9B 0.435287 0.709403 0.693000 0.080000 Uiso calc U . R 1 . .
C C10 0.3239(12) 0.459(3) 0.6563(10) 0.121(7) Uani d . . . 1 . .
H H10 0.355329 0.439333 0.700285 0.146000 Uiso calc U . R 1 . .
C C11 0.3287(10) 0.278(2) 0.6132(10) 0.100(5) Uani d . . D 1 . .
H H11 0.361772 0.194616 0.643653 0.120000 Uiso calc U . R 1 . .
C C12 0.4931(16) 0.624(7) 0.3076(9) 0.179(14) Uani d . . . 1 . .
H H12A 0.487854 0.739968 0.278832 0.268000 Uiso calc U . R 1 . .
H H12B 0.453250 0.533149 0.293926 0.268000 Uiso calc U . R 1 . .
H H12C 0.543870 0.568241 0.299450 0.268000 Uiso calc U . R 1 . .
C C13 0.2527(13) 0.178(4) 0.6154(13) 0.087(7) Uiso d . P D 0.5 . .
C C14 0.1468(10) 0.083(4) 0.5380(14) 0.076(7) Uani d . P D 0.5 . .
H H14A 0.129205 0.119507 0.490336 0.114000 Uiso calc U P R 0.5 . .
H H14B 0.108446 0.121142 0.573354 0.114000 Uiso calc U P R 0.5 . .
H H14C 0.153642 -0.055522 0.539818 0.114000 Uiso calc U P R 0.5 . .
C C15 0.2450(17) 0.510(4) 0.6796(12) 0.089(8) Uiso d . P D 0.5 . .
C C16 0.6213(6) 0.8117(17) 0.6352(6) 0.064(3) Uani d . . . 1 . .
C C17 0.6174(8) 0.639(2) 0.6713(7) 0.080(4) Uani d . . . 1 . .
H H17 0.572855 0.603960 0.697483 0.096000 Uiso calc U . R 1 . .
C C18 0.6822(8) 0.515(2) 0.6678(8) 0.088(4) Uani d . . . 1 . .
H H18 0.678626 0.394923 0.690370 0.105000 Uiso calc U . R 1 . .
C C19 0.7490(8) 0.561(3) 0.6340(7) 0.094(5) Uani d . . . 1 . .
C C20 0.7491(8) 0.740(3) 0.5967(9) 0.100(5) Uani d . . . 1 . .
H H20 0.793070 0.775935 0.569876 0.120000 Uiso calc U . R 1 . .
C C21 0.6861(7) 0.863(2) 0.5992(8) 0.085(4) Uani d . . . 1 . .
H H21 0.688414 0.982069 0.575768 0.102000 Uiso calc U . R 1 . .
C C22 0.8205(12) 0.450(5) 0.6311(13) 0.162(10) Uani d . . . 1 . .
H H22A 0.823784 0.331122 0.654859 0.194000 Uiso calc U . R 1 . .
H H22B 0.863456 0.497386 0.605476 0.194000 Uiso calc U . R 1 . .
F F1 0.2137(13) 0.357(3) 0.7165(10) 0.119(6) Uiso d . P D 0.5 . .
F F2 0.2005(12) 0.564(3) 0.6205(9) 0.111(5) Uiso d . P D 0.5 . .
F F3 0.2658(17) 0.600(5) 0.7423(13) 0.162(9) Uiso d . P D 0.5 . .
N N1 0.4689(5) 0.8583(13) 0.6031(5) 0.065(2) Uani d . . . 1 . .
N N2 0.3805(14) 0.320(2) 0.5501(11) 0.143(7) Uani d . . D 1 . .
H H2N 0.346(4) 0.324(15) 0.514(3) 0.171000 Uiso d U . D 1 . .
O O1 0.2246(18) 0.074(4) 0.6618(14) 0.130(8) Uiso d . P D 0.5 . .
O O2 0.2213(14) 0.178(4) 0.5537(12) 0.125(8) Uiso d . P D 0.5 . .
O O3 0.5587(7) 1.1369(13) 0.6041(7) 0.105(3) Uani d . . . 1 . .
O O4 0.5191(6) 0.9769(15) 0.7180(5) 0.090(3) Uani d . . . 1 . .
S S1 0.54118(18) 0.9651(4) 0.64321(17) 0.0695(12) 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
C1 C6 . 1.391(18) ?
C1 C2 . 1.412(19) ?
C1 C7 . 1.46(2) ?
C2 C3 . 1.36(3) ?
C3 C4 . 1.42(4) ?
C3 C12 . 1.51(2) ?
C4 C5 . 1.41(2) ?
C5 C6 . 1.39(2) ?
C6 N1 . 1.440(15) ?
C7 N2 . 1.43(2) ?
C7 C8 . 1.533(19) ?
C8 C10 . 1.52(2) ?
C8 C9 . 1.516(18) ?
C9 N1 . 1.504(14) ?
C10 C15 . 1.47(4) ?
C10 C11 . 1.50(3) ?
C11 C13 . 1.48(2) ?
C11 N2 . 1.50(3) ?
C13 O1 . 1.22(2) ?
C13 O2 . 1.27(2) ?
C14 O2 . 1.48(2) ?
C15 F3 . 1.37(2) ?
C15 F1 . 1.37(2) ?
C15 F2 . 1.39(2) ?
C16 C21 . 1.350(16) ?
C16 C17 . 1.382(19) ?
C16 S1 . 1.752(12) ?
C17 C18 . 1.409(19) ?
C18 C19 . 1.35(2) ?
C19 C20 . 1.43(3) ?
C19 C22 . 1.45(3) ?
C20 C21 . 1.38(2) ?
N1 S1 . 1.631(10) ?
O3 S1 . 1.432(11) ?
O4 S1 . 1.443(10) ?

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 . . 118.4(14) ?
C6 C1 C7 . . 117.9(11) ?
C2 C1 C7 . . 123.2(13) ?
C3 C2 C1 . . 122.0(18) ?
C2 C3 C4 . . 119.0(15) ?
C2 C3 C12 . . 126.(3) ?
C4 C3 C12 . . 115.(3) ?
C5 C4 C3 . . 120.3(17) ?
C6 C5 C4 . . 118.3(17) ?
C1 C6 C5 . . 121.6(13) ?
C1 C6 N1 . . 118.1(11) ?
C5 C6 N1 . . 120.3(12) ?
N2 C7 C1 . . 120.1(14) ?
N2 C7 C8 . . 104.7(14) ?
C1 C7 C8 . . 108.6(9) ?
C10 C8 C9 . . 117.8(11) ?
C10 C8 C7 . . 101.4(13) ?
C9 C8 C7 . . 108.0(9) ?
N1 C9 C8 . . 111.2(10) ?
C15 C10 C11 . . 114.3(16) ?
C15 C10 C8 . . 114.5(17) ?
C11 C10 C8 . . 105.9(16) ?
C13 C11 C10 . . 109.4(19) ?
C13 C11 N2 . . 129.6(17) ?
C10 C11 N2 . . 106.6(13) ?
O1 C13 O2 . . 118.(3) ?
O1 C13 C11 . . 130.(3) ?
O2 C13 C11 . . 111.(2) ?
F3 C15 F1 . . 92.(2) ?
F3 C15 F2 . . 134.(3) ?
F1 C15 F2 . . 113.(2) ?
F3 C15 C10 . . 97.(2) ?
F1 C15 C10 . . 109.(2) ?
F2 C15 C10 . . 110.(2) ?
C21 C16 C17 . . 120.7(13) ?
C21 C16 S1 . . 122.3(11) ?
C17 C16 S1 . . 116.9(8) ?
C16 C17 C18 . . 118.0(11) ?
C19 C18 C17 . . 123.8(14) ?
C18 C19 C20 . . 115.5(13) ?
C18 C19 C22 . . 128.1(19) ?
C20 C19 C22 . . 116.4(16) ?
C21 C20 C19 . . 121.5(12) ?
C16 C21 C20 . . 120.4(15) ?
C6 N1 C9 . . 120.5(9) ?
C6 N1 S1 . . 119.6(7) ?
C9 N1 S1 . . 116.3(8) ?
C7 N2 C11 . . 106.1(15) ?
C13 O2 C14 . . 123.(2) ?
O3 S1 O4 . . 119.7(6) ?
O3 S1 N1 . . 108.1(6) ?
O4 S1 N1 . . 105.4(5) ?
O3 S1 C16 . . 107.5(6) ?
O4 S1 C16 . . 108.9(6) ?
N1 S1 C16 . . 106.6(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 . . . . 4.(2) ?
C7 C1 C2 C3 . . . . 175.8(15) ?
C1 C2 C3 C4 . . . . -1.(3) ?
C1 C2 C3 C12 . . . . 176.3(18) ?
C2 C3 C4 C5 . . . . -5.(3) ?
C12 C3 C4 C5 . . . . 178.0(19) ?
C3 C4 C5 C6 . . . . 6.(3) ?
C2 C1 C6 C5 . . . . -2.7(18) ?
C7 C1 C6 C5 . . . . -174.6(12) ?
C2 C1 C6 N1 . . . . 175.2(10) ?
C7 C1 C6 N1 . . . . 3.3(15) ?
C4 C5 C6 C1 . . . . -2.(2) ?
C4 C5 C6 N1 . . . . 179.7(15) ?
C6 C1 C7 N2 . . . . 163.2(14) ?
C2 C1 C7 N2 . . . . -8.(2) ?
C6 C1 C7 C8 . . . . 42.9(14) ?
C2 C1 C7 C8 . . . . -128.6(12) ?
N2 C7 C8 C10 . . . . 39.3(14) ?
C1 C7 C8 C10 . . . . 168.6(10) ?
N2 C7 C8 C9 . . . . 163.7(12) ?
C1 C7 C8 C9 . . . . -66.9(11) ?
C10 C8 C9 N1 . . . . 158.4(13) ?
C7 C8 C9 N1 . . . . 44.4(12) ?
C9 C8 C10 C15 . . . . 87.6(17) ?
C7 C8 C10 C15 . . . . -154.8(15) ?
C9 C8 C10 C11 . . . . -145.5(12) ?
C7 C8 C10 C11 . . . . -27.9(15) ?
C15 C10 C11 C13 . . . . -9.(2) ?
C8 C10 C11 C13 . . . . -136.4(16) ?
C15 C10 C11 N2 . . . . 134.7(16) ?
C8 C10 C11 N2 . . . . 7.7(18) ?
C10 C11 C13 O1 . . . . -81.(3) ?
N2 C11 C13 O1 . . . . 146.(3) ?
C10 C11 C13 O2 . . . . 113.(3) ?
N2 C11 C13 O2 . . . . -20.(4) ?
C11 C10 C15 F3 . . . . 149.2(19) ?
C8 C10 C15 F3 . . . . -88.(2) ?
C11 C10 C15 F1 . . . . 55.(2) ?
C8 C10 C15 F1 . . . . 177.3(16) ?
C11 C10 C15 F2 . . . . -69.(2) ?
C8 C10 C15 F2 . . . . 53.(2) ?
C21 C16 C17 C18 . . . . -1.6(19) ?
S1 C16 C17 C18 . . . . -177.9(11) ?
C16 C17 C18 C19 . . . . 3.(2) ?
C17 C18 C19 C20 . . . . -4.(2) ?
C17 C18 C19 C22 . . . . 175.7(19) ?
C18 C19 C20 C21 . . . . 4.(2) ?
C22 C19 C20 C21 . . . . -176.1(18) ?
C17 C16 C21 C20 . . . . 1.(2) ?
S1 C16 C21 C20 . . . . 177.4(11) ?
C19 C20 C21 C16 . . . . -2.(2) ?
C1 C6 N1 C9 . . . . -26.9(15) ?
C5 C6 N1 C9 . . . . 151.0(12) ?
C1 C6 N1 S1 . . . . 131.1(9) ?
C5 C6 N1 S1 . . . . -51.0(14) ?
C8 C9 N1 C6 . . . . 0.5(14) ?
C8 C9 N1 S1 . . . . -158.2(8) ?
C1 C7 N2 C11 . . . . -157.6(13) ?
C8 C7 N2 C11 . . . . -35.4(16) ?
C13 C11 N2 C7 . . . . 152.(2) ?
C10 C11 N2 C7 . . . . 17.4(18) ?
O1 C13 O2 C14 . . . . 9.(5) ?
C11 C13 O2 C14 . . . . 177.(2) ?
C6 N1 S1 O3 . . . . 60.1(10) ?
C9 N1 S1 O3 . . . . -141.1(9) ?
C6 N1 S1 O4 . . . . -170.8(9) ?
C9 N1 S1 O4 . . . . -12.0(10) ?
C6 N1 S1 C16 . . . . -55.2(10) ?
C9 N1 S1 C16 . . . . 103.6(8) ?
C21 C16 S1 O3 . . . . 1.8(13) ?
C17 C16 S1 O3 . . . . 177.9(10) ?
C21 C16 S1 O4 . . . . -129.4(11) ?
C17 C16 S1 O4 . . . . 46.8(11) ?
C21 C16 S1 N1 . . . . 117.4(11) ?
C17 C16 S1 N1 . . . . -66.4(10) ?

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
C5 H5 O3 . 0.94 2.33 2.94(2) 121.9 ?
C9 H9B O4 3_646 0.98 2.44 3.390(15) 162.0 ?
C10 H10 O4 3_646 0.99 2.66 3.577(17) 154.8 ?
C17 H17 O4 3_646 0.94 2.40 3.322(15) 166.4 ?



####################################################################### 
# 
# 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_03196
_database_code_depnum_ccdc_archive 'CCDC 2173558'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JASOdiCl
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Cl2 F3 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         370.15
_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                   11.577(7)
_cell_length_b                   11.122(7)
_cell_length_c                   12.605(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.35(2)
_cell_angle_gamma                90
_cell_volume                     1531.3(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1507
_cell_measurement_theta_min      2.5073
_cell_measurement_theta_max      17.8801
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.98

_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       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13716
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.1625
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             5403
_reflns_number_gt                2310
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0997
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         5403
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.262
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(8)

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'
F F 0.0171 0.0103 '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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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
C C1 0.6611(8) 0.5466(8) 0.5930(8) 0.050(2) Uani d . . . 1 . .
C C2 0.7575(9) 0.4999(8) 0.5653(8) 0.055(3) Uani d . . . 1 . .
H H2 0.7422 0.4424 0.5086 0.067 Uiso calc U . R 1 . .
C C3 0.8742(9) 0.5358(9) 0.6187(9) 0.063(3) Uani d . . . 1 . .
C C4 0.9006(9) 0.6205(9) 0.7039(9) 0.064(3) Uani d . . . 1 . .
H H4 0.9803 0.646 0.741 0.076 Uiso calc U . R 1 . .
C C5 0.8049(11) 0.6642(7) 0.7305(8) 0.055(3) Uani d . . . 1 . .
C C6 0.6856(9) 0.6286(7) 0.6792(8) 0.045(2) Uani d . . . 1 . .
C C7 0.5308(8) 0.5160(7) 0.5267(7) 0.053(3) Uani d . . . 1 . .
H H7 0.5186 0.5268 0.4465 0.064 Uiso calc U . R 1 . .
C C8 0.4390(7) 0.5929(7) 0.5576(8) 0.050(2) Uani d . . . 1 . .
H H8 0.425 0.6691 0.5162 0.06 Uiso calc U . R 1 . .
C C9 0.4836(8) 0.6145(8) 0.6827(8) 0.057(3) Uani d . . . 1 . .
H H9A 0.423 0.6602 0.7034 0.068 Uiso calc U . R 1 . .
H H9B 0.4954 0.5381 0.7221 0.068 Uiso calc U . R 1 . .
C C10 0.3207(7) 0.5146(7) 0.5226(7) 0.048(2) Uani d . . . 1 . .
H H10 0.2836 0.5181 0.582 0.058 Uiso calc U . R 1 . .
C C11 0.3656(8) 0.3858(8) 0.5150(8) 0.054(3) Uani d . . . 1 . .
H H11 0.3314 0.3589 0.4367 0.065 Uiso calc U . R 1 . .
C C12 0.3297(11) 0.2976(9) 0.5877(10) 0.065(3) Uani d . . . 1 . .
C C13 0.2284(10) 0.5549(11) 0.4138(9) 0.067(3) Uani d . . . 1 . .
C C14 0.1691(9) 0.2021(9) 0.6336(9) 0.088(4) Uani d . . . 1 . .
H H14A 0.2121 0.1269 0.6432 0.132 Uiso calc U . R 1 . .
H H14B 0.083 0.1882 0.5989 0.132 Uiso calc U . R 1 . .
H H14C 0.1839 0.2392 0.7057 0.132 Uiso calc U . R 1 . .
C C15 0.6438(8) 0.5263(8) 0.1092(8) 0.055(3) Uani d . . . 1 . .
C C16 0.7320(9) 0.5574(8) 0.0646(8) 0.058(3) Uani d . . . 1 . .
H H16 0.7159 0.6129 0.0062 0.069 Uiso calc U . R 1 . .
C C17 0.8471(9) 0.5040(9) 0.1086(9) 0.056(3) Uani d . . . 1 . .
C C18 0.8730(8) 0.4202(8) 0.1909(9) 0.058(3) Uani d . . . 1 . .
H H18 0.9502 0.3852 0.2179 0.07 Uiso calc U . R 1 . .
C C19 0.7815(9) 0.3876(7) 0.2340(7) 0.048(3) Uani d . . . 1 . .
C C20 0.6685(8) 0.4408(8) 0.1931(8) 0.048(2) Uani d . . . 1 . .
C C21 0.5214(8) 0.5877(8) 0.0713(8) 0.057(3) Uani d . . . 1 . .
H H21 0.5342 0.6746 0.0689 0.068 Uiso calc U . R 1 . .
C C22 0.4464(7) 0.5628(7) 0.1481(7) 0.044(2) Uani d . . . 1 . .
H H22 0.472 0.6153 0.2143 0.053 Uiso calc U . R 1 . .
C C23 0.4608(7) 0.4347(8) 0.1815(8) 0.056(3) Uani d . . . 1 . .
H H23A 0.4094 0.4168 0.2266 0.067 Uiso calc U . R 1 . .
H H23B 0.4337 0.3848 0.1146 0.067 Uiso calc U . R 1 . .
C C24 0.3155(7) 0.5896(8) 0.0750(7) 0.052(2) Uani d . . . 1 . .
H H24 0.2598 0.5344 0.0948 0.062 Uiso calc U . R 1 . .
C C25 0.3153(8) 0.5600(9) -0.0478(8) 0.061(3) Uani d . . . 1 . .
H H25 0.2791 0.6275 -0.0976 0.073 Uiso calc U . R 1 . .
C C26 0.2445(10) 0.4490(12) -0.0923(8) 0.066(3) Uani d . . . 1 . .
C C27 0.2777(10) 0.7162(10) 0.0854(12) 0.073(3) Uani d . . . 1 . .
C C28 0.0509(9) 0.3562(9) -0.1407(9) 0.100(4) Uani d . . . 1 . .
H H28A -0.0031 0.366 -0.2166 0.15 Uiso calc U . R 1 . .
H H28B 0.0036 0.3468 -0.0915 0.15 Uiso calc U . R 1 . .
H H28C 0.1008 0.2862 -0.136 0.15 Uiso calc U . R 1 . .
Cl Cl1 0.9958(2) 0.4765(3) 0.5812(2) 0.0899(9) Uani d . . . 1 . .
Cl Cl2 0.8346(2) 0.7744(2) 0.8362(2) 0.0723(8) Uani d . . . 1 . .
Cl Cl3 0.9616(2) 0.5425(2) 0.0523(3) 0.0926(10) Uani d . . . 1 . .
Cl Cl4 0.8153(2) 0.2781(2) 0.3380(2) 0.0776(8) Uani d . . . 1 . .
F F1 0.1887(5) 0.6666(5) 0.4215(5) 0.091(2) Uani d . . . 1 . .
F F2 0.1296(5) 0.4854(6) 0.3834(4) 0.0836(18) Uani d . . . 1 . .
F F3 0.2758(5) 0.5535(5) 0.3306(5) 0.0832(17) Uani d . . . 1 . .
F F4 0.2756(6) 0.7445(5) 0.1846(6) 0.102(2) Uani d . . . 1 . .
F F5 0.1622(5) 0.7375(5) 0.0140(5) 0.097(2) Uani d . . . 1 . .
F F6 0.3488(5) 0.7959(5) 0.0583(5) 0.0890(19) Uani d . . . 1 . .
N N1 0.4993(7) 0.3916(6) 0.5453(7) 0.064(2) Uani d . . . 1 . .
H H1 0.5498 0.3331 0.5695 0.077 Uiso calc U . R 1 . .
N N2 0.4444(6) 0.5483(8) -0.0384(6) 0.072(2) Uani d . . . 1 . .
H H2A 0.4704 0.5219 -0.0905 0.086 Uiso calc U . R 1 . .
O O1 0.5977(6) 0.6798(5) 0.7146(5) 0.0581(18) Uani d . . . 1 . .
O O2 0.4041(7) 0.2532(7) 0.6682(8) 0.119(3) Uani d . . . 1 . .
O O3 0.2130(7) 0.2822(6) 0.5614(5) 0.0666(18) Uani d . . . 1 . .
O O4 0.5870(5) 0.4056(5) 0.2452(5) 0.0576(17) Uani d . . . 1 . .
O O5 0.2887(7) 0.3587(8) -0.1097(8) 0.130(4) Uani d . . . 1 . .
O O6 0.1292(6) 0.4622(6) -0.1071(5) 0.075(2) 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
C1 C6 . 1.374(11) ?
C1 C2 . 1.377(11) ?
C1 C7 . 1.501(11) ?
C2 C3 . 1.355(11) ?
C2 H2 . 0.93 ?
C3 C4 . 1.384(12) ?
C3 Cl1 . 1.754(9) ?
C4 C5 . 1.350(12) ?
C4 H4 . 0.93 ?
C5 C6 . 1.375(11) ?
C5 Cl2 . 1.759(9) ?
C6 O1 . 1.364(10) ?
C7 N1 . 1.469(10) ?
C7 C8 . 1.513(11) ?
C7 H7 . 0.98 ?
C8 C9 . 1.507(11) ?
C8 C10 . 1.558(10) ?
C8 H8 . 0.98 ?
C9 O1 . 1.443(9) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C13 . 1.501(12) ?
C10 C11 . 1.537(11) ?
C10 H10 . 0.98 ?
C11 N1 . 1.468(10) ?
C11 C12 . 1.493(13) ?
C11 H11 . 0.98 ?
C12 O2 . 1.198(10) ?
C12 O3 . 1.292(11) ?
C13 F2 . 1.328(10) ?
C13 F3 . 1.333(11) ?
C13 F1 . 1.340(11) ?
C14 O3 . 1.479(10) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 C16 . 1.365(11) ?
C15 C20 . 1.379(11) ?
C15 C21 . 1.501(11) ?
C16 C17 . 1.395(12) ?
C16 H16 . 0.93 ?
C17 C18 . 1.352(11) ?
C17 Cl3 . 1.751(9) ?
C18 C19 . 1.389(12) ?
C18 H18 . 0.93 ?
C19 C20 . 1.371(11) ?
C19 Cl4 . 1.737(9) ?
C20 O4 . 1.374(10) ?
C21 N2 . 1.443(10) ?
C21 C22 . 1.525(11) ?
C21 H21 . 0.98 ?
C22 C23 . 1.480(10) ?
C22 C24 . 1.520(10) ?
C22 H22 . 0.98 ?
C23 O4 . 1.451(9) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 C27 . 1.493(13) ?
C24 C25 . 1.581(11) ?
C24 H24 . 0.98 ?
C25 N2 . 1.465(9) ?
C25 C26 . 1.486(13) ?
C25 H25 . 0.98 ?
C26 O5 . 1.180(12) ?
C26 O6 . 1.293(11) ?
C27 F4 . 1.297(12) ?
C27 F6 . 1.329(11) ?
C27 F5 . 1.363(11) ?
C28 O6 . 1.462(10) ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
N1 H1 . 0.86 ?
N2 H2A . 0.86 ?

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 . . 118.6(8) ?
C6 C1 C7 . . 119.8(9) ?
C2 C1 C7 . . 121.5(9) ?
C3 C2 C1 . . 121.4(9) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
C2 C3 C4 . . 120.9(9) ?
C2 C3 Cl1 . . 120.8(9) ?
C4 C3 Cl1 . . 118.3(9) ?
C5 C4 C3 . . 116.7(9) ?
C5 C4 H4 . . 121.7 ?
C3 C4 H4 . . 121.7 ?
C4 C5 C6 . . 124.0(9) ?
C4 C5 Cl2 . . 118.0(9) ?
C6 C5 Cl2 . . 118.0(9) ?
O1 C6 C1 . . 123.7(9) ?
O1 C6 C5 . . 117.9(9) ?
C1 C6 C5 . . 118.3(9) ?
N1 C7 C1 . . 112.4(7) ?
N1 C7 C8 . . 104.9(7) ?
C1 C7 C8 . . 113.0(8) ?
N1 C7 H7 . . 108.8 ?
C1 C7 H7 . . 108.8 ?
C8 C7 H7 . . 108.8 ?
C9 C8 C7 . . 109.5(7) ?
C9 C8 C10 . . 110.4(7) ?
C7 C8 C10 . . 103.8(7) ?
C9 C8 H8 . . 111.0 ?
C7 C8 H8 . . 111.0 ?
C10 C8 H8 . . 111.0 ?
O1 C9 C8 . . 109.7(7) ?
O1 C9 H9A . . 109.7 ?
C8 C9 H9A . . 109.7 ?
O1 C9 H9B . . 109.7 ?
C8 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C13 C10 C11 . . 112.0(7) ?
C13 C10 C8 . . 112.6(8) ?
C11 C10 C8 . . 104.7(6) ?
C13 C10 H10 . . 109.1 ?
C11 C10 H10 . . 109.1 ?
C8 C10 H10 . . 109.1 ?
N1 C11 C12 . . 110.7(8) ?
N1 C11 C10 . . 107.0(6) ?
C12 C11 C10 . . 113.9(8) ?
N1 C11 H11 . . 108.4 ?
C12 C11 H11 . . 108.4 ?
C10 C11 H11 . . 108.4 ?
O2 C12 O3 . . 124.0(11) ?
O2 C12 C11 . . 121.5(10) ?
O3 C12 C11 . . 114.2(9) ?
F2 C13 F3 . . 107.8(9) ?
F2 C13 F1 . . 106.1(8) ?
F3 C13 F1 . . 108.0(10) ?
F2 C13 C10 . . 112.0(9) ?
F3 C13 C10 . . 111.2(8) ?
F1 C13 C10 . . 111.6(8) ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 119.8(9) ?
C16 C15 C21 . . 120.6(9) ?
C20 C15 C21 . . 119.5(9) ?
C15 C16 C17 . . 118.3(9) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C18 C17 C16 . . 122.6(9) ?
C18 C17 Cl3 . . 118.3(8) ?
C16 C17 Cl3 . . 119.1(8) ?
C17 C18 C19 . . 118.4(9) ?
C17 C18 H18 . . 120.8 ?
C19 C18 H18 . . 120.8 ?
C20 C19 C18 . . 119.8(9) ?
C20 C19 Cl4 . . 122.3(9) ?
C18 C19 Cl4 . . 117.9(8) ?
C19 C20 O4 . . 114.8(9) ?
C19 C20 C15 . . 121.0(9) ?
O4 C20 C15 . . 124.1(8) ?
N2 C21 C15 . . 112.7(8) ?
N2 C21 C22 . . 104.7(7) ?
C15 C21 C22 . . 113.0(8) ?
N2 C21 H21 . . 108.8 ?
C15 C21 H21 . . 108.8 ?
C22 C21 H21 . . 108.8 ?
C23 C22 C24 . . 110.9(7) ?
C23 C22 C21 . . 108.7(8) ?
C24 C22 C21 . . 104.0(7) ?
C23 C22 H22 . . 111.0 ?
C24 C22 H22 . . 111.0 ?
C21 C22 H22 . . 111.0 ?
O4 C23 C22 . . 111.7(7) ?
O4 C23 H23A . . 109.3 ?
C22 C23 H23A . . 109.3 ?
O4 C23 H23B . . 109.3 ?
C22 C23 H23B . . 109.3 ?
H23A C23 H23B . . 107.9 ?
C27 C24 C22 . . 113.2(8) ?
C27 C24 C25 . . 112.2(8) ?
C22 C24 C25 . . 103.3(7) ?
C27 C24 H24 . . 109.3 ?
C22 C24 H24 . . 109.3 ?
C25 C24 H24 . . 109.3 ?
N2 C25 C26 . . 112.2(8) ?
N2 C25 C24 . . 105.6(7) ?
C26 C25 C24 . . 111.4(8) ?
N2 C25 H25 . . 109.2 ?
C26 C25 H25 . . 109.2 ?
C24 C25 H25 . . 109.2 ?
O5 C26 O6 . . 124.1(11) ?
O5 C26 C25 . . 123.9(10) ?
O6 C26 C25 . . 112.0(10) ?
F4 C27 F6 . . 107.3(11) ?
F4 C27 F5 . . 105.5(9) ?
F6 C27 F5 . . 105.7(9) ?
F4 C27 C24 . . 114.4(10) ?
F6 C27 C24 . . 112.4(9) ?
F5 C27 C24 . . 111.0(9) ?
O6 C28 H28A . . 109.5 ?
O6 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O6 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C11 N1 C7 . . 107.2(6) ?
C11 N1 H1 . . 126.4 ?
C7 N1 H1 . . 126.4 ?
C21 N2 C25 . . 109.9(7) ?
C21 N2 H2A . . 125.1 ?
C25 N2 H2A . . 125.1 ?
C6 O1 C9 . . 114.3(7) ?
C12 O3 C14 . . 117.8(8) ?
C20 O4 C23 . . 113.4(7) ?
C26 O6 C28 . . 117.5(8) ?

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 . . . . -2.0(13) ?
C7 C1 C2 C3 . . . . 174.0(8) ?
C1 C2 C3 C4 . . . . 0.5(14) ?
C1 C2 C3 Cl1 . . . . -179.3(7) ?
C2 C3 C4 C5 . . . . 0.2(14) ?
Cl1 C3 C4 C5 . . . . -180.0(7) ?
C3 C4 C5 C6 . . . . 0.7(14) ?
C3 C4 C5 Cl2 . . . . -178.6(7) ?
C2 C1 C6 O1 . . . . -179.3(8) ?
C7 C1 C6 O1 . . . . 4.7(13) ?
C2 C1 C6 C5 . . . . 2.7(12) ?
C7 C1 C6 C5 . . . . -173.3(7) ?
C4 C5 C6 O1 . . . . 179.7(8) ?
Cl2 C5 C6 O1 . . . . -1.0(10) ?
C4 C5 C6 C1 . . . . -2.2(13) ?
Cl2 C5 C6 C1 . . . . 177.1(7) ?
C6 C1 C7 N1 . . . . -112.5(9) ?
C2 C1 C7 N1 . . . . 71.6(11) ?
C6 C1 C7 C8 . . . . 6.1(12) ?
C2 C1 C7 C8 . . . . -169.8(8) ?
N1 C7 C8 C9 . . . . 84.6(8) ?
C1 C7 C8 C9 . . . . -38.2(10) ?
N1 C7 C8 C10 . . . . -33.3(8) ?
C1 C7 C8 C10 . . . . -156.2(7) ?
C7 C8 C9 O1 . . . . 62.3(9) ?
C10 C8 C9 O1 . . . . 176.0(6) ?
C9 C8 C10 C13 . . . . 140.6(8) ?
C7 C8 C10 C13 . . . . -102.2(8) ?
C9 C8 C10 C11 . . . . -97.5(8) ?
C7 C8 C10 C11 . . . . 19.7(9) ?
C13 C10 C11 N1 . . . . 123.2(9) ?
C8 C10 C11 N1 . . . . 0.9(10) ?
C13 C10 C11 C12 . . . . -114.2(10) ?
C8 C10 C11 C12 . . . . 123.5(8) ?
N1 C11 C12 O2 . . . . 9.4(13) ?
C10 C11 C12 O2 . . . . -111.2(11) ?
N1 C11 C12 O3 . . . . -176.0(7) ?
C10 C11 C12 O3 . . . . 63.4(11) ?
C11 C10 C13 F2 . . . . 60.5(11) ?
C8 C10 C13 F2 . . . . 178.3(8) ?
C11 C10 C13 F3 . . . . -60.1(11) ?
C8 C10 C13 F3 . . . . 57.6(11) ?
C11 C10 C13 F1 . . . . 179.3(8) ?
C8 C10 C13 F1 . . . . -63.0(11) ?
C20 C15 C16 C17 . . . . -2.2(13) ?
C21 C15 C16 C17 . . . . 175.4(8) ?
C15 C16 C17 C18 . . . . 2.1(13) ?
C15 C16 C17 Cl3 . . . . 179.9(7) ?
C16 C17 C18 C19 . . . . -0.9(13) ?
Cl3 C17 C18 C19 . . . . -178.7(7) ?
C17 C18 C19 C20 . . . . -0.3(13) ?
C17 C18 C19 Cl4 . . . . 179.0(6) ?
C18 C19 C20 O4 . . . . -177.3(8) ?
Cl4 C19 C20 O4 . . . . 3.5(10) ?
C18 C19 C20 C15 . . . . 0.2(12) ?
Cl4 C19 C20 C15 . . . . -179.0(7) ?
C16 C15 C20 C19 . . . . 1.1(13) ?
C21 C15 C20 C19 . . . . -176.5(8) ?
C16 C15 C20 O4 . . . . 178.3(8) ?
C21 C15 C20 O4 . . . . 0.7(13) ?
C16 C15 C21 N2 . . . . 75.0(11) ?
C20 C15 C21 N2 . . . . -107.4(9) ?
C16 C15 C21 C22 . . . . -166.7(8) ?
C20 C15 C21 C22 . . . . 10.9(12) ?
N2 C21 C22 C23 . . . . 82.1(8) ?
C15 C21 C22 C23 . . . . -40.9(10) ?
N2 C21 C22 C24 . . . . -36.1(9) ?
C15 C21 C22 C24 . . . . -159.0(7) ?
C24 C22 C23 O4 . . . . 176.3(7) ?
C21 C22 C23 O4 . . . . 62.5(9) ?
C23 C22 C24 C27 . . . . 151.1(9) ?
C21 C22 C24 C27 . . . . -92.2(10) ?
C23 C22 C24 C25 . . . . -87.4(9) ?
C21 C22 C24 C25 . . . . 29.3(8) ?
C27 C24 C25 N2 . . . . 109.4(9) ?
C22 C24 C25 N2 . . . . -12.8(9) ?
C27 C24 C25 C26 . . . . -128.6(9) ?
C22 C24 C25 C26 . . . . 109.2(8) ?
N2 C25 C26 O5 . . . . 5.6(15) ?
C24 C25 C26 O5 . . . . -112.5(12) ?
N2 C25 C26 O6 . . . . -175.9(7) ?
C24 C25 C26 O6 . . . . 65.9(10) ?
C22 C24 C27 F4 . . . . -64.0(12) ?
C25 C24 C27 F4 . . . . 179.6(9) ?
C22 C24 C27 F6 . . . . 58.7(13) ?
C25 C24 C27 F6 . . . . -57.7(12) ?
C22 C24 C27 F5 . . . . 176.8(8) ?
C25 C24 C27 F5 . . . . 60.4(11) ?
C12 C11 N1 C7 . . . . -146.7(7) ?
C10 C11 N1 C7 . . . . -22.1(9) ?
C1 C7 N1 C11 . . . . 158.3(8) ?
C8 C7 N1 C11 . . . . 35.1(9) ?
C15 C21 N2 C25 . . . . 151.8(8) ?
C22 C21 N2 C25 . . . . 28.7(9) ?
C26 C25 N2 C21 . . . . -131.3(8) ?
C24 C25 N2 C21 . . . . -9.8(9) ?
C1 C6 O1 C9 . . . . 19.7(11) ?
C5 C6 O1 C9 . . . . -162.3(7) ?
C8 C9 O1 C6 . . . . -53.2(9) ?
O2 C12 O3 C14 . . . . -1.8(14) ?
C11 C12 O3 C14 . . . . -176.2(8) ?
C19 C20 O4 C23 . . . . -163.2(7) ?
C15 C20 O4 C23 . . . . 19.4(11) ?
C22 C23 O4 C20 . . . . -51.9(10) ?
O5 C26 O6 C28 . . . . 4.0(16) ?
C25 C26 O6 C28 . . . . -174.4(8) ?

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
C9 H9A Cl4 2_656 0.97 2.94 3.841(9) 154.9 ?
C14 H14C O5 1_556 0.96 2.60 3.528(14) 161.6 ?
C21 H21 F6 . 0.98 2.50 3.027(10) 113.4 ?
C22 H22 O2 2_656 0.98 2.28 3.191(12) 154.3 ?
C28 H28A Cl1 1_454 0.96 2.83 3.606(11) 139.0 ?
C28 H28B Cl3 1_455 0.96 2.97 3.598(12) 123.9 ?



