# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_osm-ms-1197
_database_code_depnum_ccdc_archive 'CCDC 1562038'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
# start Validation Reply Form
_vrf_PLAT097_osm-ms-1197         
;
PROBLEM:  Large Reported Max.  (Positive) Residual Density       3.76 eA-3  
RESPONSE: There is a disorder of chlorine atoms in the trichloromethyl groups.  
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 Cl3 N O2'
_chemical_formula_sum            'C7 H10 Cl3 N O2'
_chemical_formula_weight         246.5205

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3657(2)
_cell_length_b                   12.7989(2)
_cell_length_c                   18.2787(4)
_cell_angle_alpha                81.7120(10)
_cell_angle_beta                 75.2110(10)
_cell_angle_gamma                67.7120(10)
_cell_volume                     2166.48(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    19787
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18157
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         30.04
_reflns_number_total             12592
_reflns_number_gt                6830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1508P)²+7.8684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12592
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1819
_refine_ls_R_factor_gt           0.1060
_refine_ls_wR_factor_ref         0.3268
_refine_ls_wR_factor_gt          0.2767
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3915(4) 0.3298(3) 0.4413(2) 0.1284(15) Uani 1 1 d . . .
Cl2 Cl 0.1346(4) 0.3273(2) 0.41400(19) 0.1196(14) Uani 1 1 d . . .
Cl3 Cl 0.1392(2) 0.39735(15) 0.55460(10) 0.0571(5) Uani 1 1 d . . .
Cl4 Cl 0.2538(3) 0.7811(2) 0.81972(11) 0.0823(8) Uani 1 1 d . . .
Cl5 Cl 0.5585(3) 0.6865(2) 0.77985(12) 0.0765(7) Uani 1 1 d . . .
Cl6 Cl 0.3927(3) 0.59730(17) 0.72205(9) 0.0582(5) Uani 1 1 d . . .
Cl7 Cl 0.0012(2) 0.06255(15) 0.89021(10) 0.0484(4) Uani 1 1 d . . .
Cl8 Cl -0.02976(17) 0.21078(14) 1.00348(8) 0.0426(4) Uani 1 1 d . . .
Cl9 Cl 0.24436(16) 0.04528(16) 0.94703(10) 0.0498(4) Uani 1 1 d . . .
Cl10 Cl 0.87028(18) -0.09270(14) 0.82265(10) 0.0465(4) Uani 1 1 d . . .
Cl11 Cl 0.5634(2) -0.00414(19) 0.83575(14) 0.0728(7) Uani 1 1 d . . .
Cl12 Cl 0.7539(2) -0.11557(14) 0.70291(12) 0.0561(5) Uani 1 1 d . . .
C1 C 0.2301(8) 0.3022(6) 0.4832(3) 0.0485(17) Uani 1 1 d . . .
O7 O 0.8075(4) 0.1338(3) 0.7580(2) 0.0328(9) Uani 1 1 d . . .
O5 O 0.2394(4) 0.2080(3) 0.8225(2) 0.0317(8) Uani 1 1 d . . .
N2 N 0.4310(4) 0.4681(4) 0.8669(2) 0.0251(9) Uani 1 1 d . . .
H31 H 0.4342 0.4468 0.8237 0.030 Uiso 1 1 calc R . .
O6 O -0.0283(5) 0.2675(4) 0.6942(2) 0.0393(10) Uani 1 1 d . . .
H51 H -0.0776 0.2294 0.7136 0.059 Uiso 1 1 calc R . .
O3 O 0.3898(5) 0.6192(4) 0.9331(2) 0.0427(11) Uani 1 1 d . . .
N1 N 0.2213(5) 0.1492(4) 0.5794(2) 0.0263(9) Uani 1 1 d . . .
H32 H 0.1550 0.2010 0.6069 0.032 Uiso 1 1 calc R . .
O2 O 0.4755(4) 0.0585(4) 0.6337(3) 0.0367(9) Uani 1 1 d . . .
H50 H 0.5380 0.0086 0.6076 0.055 Uiso 1 1 calc R . .
N3 N 0.0003(5) 0.3060(4) 0.8416(3) 0.0300(10) Uani 1 1 d . . .
H30 H -0.0801 0.3123 0.8723 0.036 Uiso 1 1 calc R . .
O4 O 0.7045(4) 0.3593(4) 0.9118(2) 0.0366(9) Uani 1 1 d . . .
H52 H 0.6950 0.3796 0.9541 0.055 Uiso 1 1 calc R . .
O8 O 0.4076(5) 0.3361(4) 0.7553(2) 0.0366(9) Uani 1 1 d . . .
H88 H 0.3796 0.2849 0.7759 0.055 Uiso 1 1 calc R . .
C8 C 0.3994(6) 0.6559(5) 0.8019(3) 0.0291(11) Uani 1 1 d . . .
N4 N 0.6467(5) 0.1393(4) 0.6920(3) 0.0318(10) Uani 1 1 d . . .
H33 H 0.6043 0.1000 0.6803 0.038 Uiso 1 1 calc R . .
C24 C 0.6197(6) 0.2544(5) 0.6577(3) 0.0269(10) Uani 1 1 d . . .
H1 H 0.6665 0.2912 0.6804 0.032 Uiso 1 1 calc R . .
C10 C 0.4544(5) 0.3840(5) 0.9311(3) 0.0265(11) Uani 1 1 d . . .
H2 H 0.4396 0.4247 0.9758 0.032 Uiso 1 1 calc R . .
C16 C 0.1164(5) 0.2240(5) 0.8560(3) 0.0249(10) Uani 1 1 d . . .
C9 C 0.4051(5) 0.5762(5) 0.8747(3) 0.0263(11) Uani 1 1 d . . .
C15 C 0.0865(6) 0.1387(5) 0.9215(3) 0.0282(11) Uani 1 1 d . . .
C17 C 0.0011(5) 0.3871(5) 0.7761(3) 0.0265(10) Uani 1 1 d . . .
H6 H 0.0995 0.3681 0.7465 0.032 Uiso 1 1 calc R . .
O1 O 0.3651(6) 0.1115(4) 0.4627(3) 0.0639(16) Uani 1 1 d . . .
C11 C 0.3474(6) 0.3250(6) 0.9485(3) 0.0351(13) Uani 1 1 d . . .
H8 H 0.3558 0.2740 0.9109 0.042 Uiso 1 1 calc R . .
C21 C -0.0901(6) 0.3749(5) 0.7265(3) 0.0306(11) Uani 1 1 d . . .
H9A H -0.1850 0.3840 0.7567 0.037 Uiso 1 1 calc R . .
H9B H -0.0994 0.4339 0.6863 0.037 Uiso 1 1 calc R . .
C23 C 0.7321(6) 0.0926(5) 0.7395(3) 0.0273(11) Uani 1 1 d . . .
C18 C -0.0498(6) 0.5050(5) 0.8009(3) 0.0314(12) Uani 1 1 d . . .
H11 H -0.1503 0.5363 0.8272 0.038 Uiso 1 1 calc R . .
C22 C 0.7305(6) -0.0245(5) 0.7748(4) 0.0342(12) Uani 1 1 d . . .
C7 C 0.3581(6) 0.0232(5) 0.6679(3) 0.0321(12) Uani 1 1 d . . .
H12A H 0.2985 0.0700 0.7100 0.039 Uiso 1 1 calc R . .
H12B H 0.3934 -0.0545 0.6876 0.039 Uiso 1 1 calc R . .
C14 C 0.6079(6) 0.3032(5) 0.9151(3) 0.0335(12) Uani 1 1 d . . .
H13A H 0.6205 0.2431 0.9546 0.040 Uiso 1 1 calc R . .
H13B H 0.6292 0.2692 0.8673 0.040 Uiso 1 1 calc R . .
C3 C 0.2694(6) 0.0324(4) 0.6108(3) 0.0263(10) Uani 1 1 d . . .
H14 H 0.3319 -0.0159 0.5693 0.032 Uiso 1 1 calc R . .
C25 C 0.6810(7) 0.2514(5) 0.5732(3) 0.0385(13) Uani 1 1 d . . .
H15 H 0.6460 0.2119 0.5450 0.046 Uiso 1 1 calc R . .
C4 C 0.1467(6) -0.0081(5) 0.6446(3) 0.0324(12) Uani 1 1 d . . .
H16 H 0.0854 0.0229 0.6928 0.039 Uiso 1 1 calc R . .
C28 C 0.4597(6) 0.3193(5) 0.6764(3) 0.0305(11) Uani 1 1 d . . .
H17A H 0.4388 0.3922 0.6485 0.037 Uiso 1 1 calc R . .
H17B H 0.4112 0.2779 0.6605 0.037 Uiso 1 1 calc R . .
C5 C 0.1673(7) -0.1267(6) 0.6326(4) 0.0410(14) Uani 1 1 d . . .
H18A H 0.1205 -0.1668 0.6730 0.049 Uiso 1 1 calc R . .
H18B H 0.2597 -0.1734 0.6045 0.049 Uiso 1 1 calc R . .
C2 C 0.2776(6) 0.1758(5) 0.5099(3) 0.0345(12) Uani 1 1 d . . .
C20 C 0.0101(9) 0.5881(6) 0.7508(4) 0.0495(17) Uani 1 1 d . . .
H20A H 0.0816 0.5609 0.7050 0.059 Uiso 1 1 calc R . .
H20B H -0.0540 0.6659 0.7465 0.059 Uiso 1 1 calc R . .
C12 C 0.2979(7) 0.2933(6) 1.0300(4) 0.0448(16) Uani 1 1 d . . .
H21A H 0.2776 0.2240 1.0415 0.054 Uiso 1 1 calc R . .
H21B H 0.3376 0.3111 1.0671 0.054 Uiso 1 1 calc R . .
C19 C 0.0513(7) 0.5449(6) 0.8253(4) 0.0427(15) Uani 1 1 d . . .
H23A H 0.0121 0.5967 0.8659 0.051 Uiso 1 1 calc R . .
H23B H 0.1476 0.4917 0.8245 0.051 Uiso 1 1 calc R . .
C13 C 0.2008(7) 0.3890(7) 0.9906(4) 0.0481(17) Uani 1 1 d . . .
H25A H 0.1813 0.4650 1.0040 0.058 Uiso 1 1 calc R . .
H25B H 0.1213 0.3779 0.9784 0.058 Uiso 1 1 calc R . .
C26 C 0.7034(9) 0.3570(7) 0.5338(4) 0.059(2) Uani 1 1 d . . .
H26A H 0.6850 0.4186 0.5648 0.071 Uiso 1 1 calc R . .
H26B H 0.6803 0.3800 0.4843 0.071 Uiso 1 1 calc R . .
C27 C 0.8314(11) 0.2490(9) 0.5404(5) 0.073(3) Uani 1 1 d . . .
H27A H 0.8842 0.2081 0.4950 0.088 Uiso 1 1 calc R . .
H27B H 0.8888 0.2466 0.5755 0.088 Uiso 1 1 calc R . .
C6 C 0.0744(7) -0.0300(6) 0.5897(4) 0.0427(15) Uani 1 1 d . . .
H10A H 0.1112 -0.0183 0.5360 0.051 Uiso 1 1 calc R . .
H10B H -0.0281 -0.0118 0.6046 0.051 Uiso 1 1 calc R . .


_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 C1 1.796(8) . ?
Cl2 C1 1.721(8) . ?
Cl3 C1 1.742(7) . ?
Cl4 C8 1.738(6) . ?
Cl5 C8 1.772(6) . ?
Cl6 C8 1.761(5) . ?
Cl7 C15 1.770(6) . ?
Cl8 C15 1.784(6) . ?
Cl9 C15 1.752(6) . ?
Cl10 C22 1.759(6) . ?
Cl11 C22 1.751(6) . ?
Cl12 C22 1.792(7) . ?
C1 C2 1.545(9) . ?
O7 C23 1.226(6) . ?
O5 C16 1.218(6) . ?
N2 C9 1.327(7) . ?
N2 C10 1.476(6) . ?
N2 H31 0.8600 . ?
O6 C21 1.421(7) . ?
O6 H51 0.8200 . ?
O3 C9 1.218(7) . ?
N1 C2 1.311(7) . ?
N1 C3 1.465(7) . ?
N1 H32 0.8600 . ?
O2 C7 1.421(7) . ?
O2 H50 0.8200 . ?
N3 C16 1.321(7) . ?
N3 C17 1.468(7) . ?
N3 H30 0.8600 . ?
O4 C14 1.424(7) . ?
O4 H52 0.8200 . ?
O8 C28 1.422(7) . ?
O8 H88 0.8200 . ?
C8 C9 1.555(7) . ?
N4 C23 1.318(7) . ?
N4 C24 1.466(7) . ?
N4 H33 0.8600 . ?
C24 C25 1.514(8) . ?
C24 C28 1.518(7) . ?
C24 H1 0.9800 . ?
C10 C11 1.512(7) . ?
C10 C14 1.512(8) . ?
C10 H2 0.9800 . ?
C16 C15 1.553(7) . ?
C17 C18 1.494(8) . ?
C17 C21 1.527(8) . ?
C17 H6 0.9800 . ?
O1 C2 1.217(7) . ?
C11 C13 1.488(9) . ?
C11 C12 1.496(8) . ?
C11 H8 0.9800 . ?
C21 H9A 0.9700 . ?
C21 H9B 0.9700 . ?
C23 C22 1.548(8) . ?
C18 C19 1.505(8) . ?
C18 C20 1.512(9) . ?
C18 H11 0.9800 . ?
C7 C3 1.523(7) . ?
C7 H12A 0.9700 . ?
C7 H12B 0.9700 . ?
C14 H13A 0.9700 . ?
C14 H13B 0.9700 . ?
C3 C4 1.508(8) . ?
C3 H14 0.9800 . ?
C25 C26 1.506(10) . ?
C25 C27 1.511(11) . ?
C25 H15 0.9800 . ?
C4 C5 1.492(9) . ?
C4 C6 1.506(8) . ?
C4 H16 0.9800 . ?
C28 H17A 0.9700 . ?
C28 H17B 0.9700 . ?
C5 C6 1.508(9) . ?
C5 H18A 0.9700 . ?
C5 H18B 0.9700 . ?
C20 C19 1.497(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C12 C13 1.487(10) . ?
C12 H21A 0.9700 . ?
C12 H21B 0.9700 . ?
C19 H23A 0.9700 . ?
C19 H23B 0.9700 . ?
C13 H25A 0.9700 . ?
C13 H25B 0.9700 . ?
C26 C27 1.525(14) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C6 H10A 0.9700 . ?
C6 H10B 0.9700 . ?

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 C1 Cl2 110.3(5) . . ?
C2 C1 Cl3 115.6(4) . . ?
Cl2 C1 Cl3 111.2(4) . . ?
C2 C1 Cl1 106.0(5) . . ?
Cl2 C1 Cl1 107.9(4) . . ?
Cl3 C1 Cl1 105.3(5) . . ?
C9 N2 C10 121.0(4) . . ?
C9 N2 H31 119.5 . . ?
C10 N2 H31 119.5 . . ?
C21 O6 H51 109.5 . . ?
C2 N1 C3 121.0(5) . . ?
C2 N1 H32 119.5 . . ?
C3 N1 H32 119.5 . . ?
C7 O2 H50 109.5 . . ?
C16 N3 C17 123.6(4) . . ?
C16 N3 H30 118.2 . . ?
C17 N3 H30 118.2 . . ?
C14 O4 H52 109.5 . . ?
C28 O8 H88 109.5 . . ?
C9 C8 Cl4 109.9(4) . . ?
C9 C8 Cl6 114.7(4) . . ?
Cl4 C8 Cl6 109.1(3) . . ?
C9 C8 Cl5 106.4(4) . . ?
Cl4 C8 Cl5 108.9(3) . . ?
Cl6 C8 Cl5 107.6(3) . . ?
C23 N4 C24 124.0(4) . . ?
C23 N4 H33 118.0 . . ?
C24 N4 H33 118.0 . . ?
N4 C24 C25 110.5(5) . . ?
N4 C24 C28 108.3(4) . . ?
C25 C24 C28 112.1(5) . . ?
N4 C24 H1 108.6 . . ?
C25 C24 H1 108.6 . . ?
C28 C24 H1 108.6 . . ?
N2 C10 C11 111.3(4) . . ?
N2 C10 C14 109.4(4) . . ?
C11 C10 C14 113.2(5) . . ?
N2 C10 H2 107.6 . . ?
C11 C10 H2 107.6 . . ?
C14 C10 H2 107.6 . . ?
O5 C16 N3 127.1(5) . . ?
O5 C16 C15 118.8(5) . . ?
N3 C16 C15 114.1(4) . . ?
O3 C9 N2 126.6(5) . . ?
O3 C9 C8 116.1(5) . . ?
N2 C9 C8 117.3(4) . . ?
C16 C15 Cl9 111.6(3) . . ?
C16 C15 Cl7 107.6(3) . . ?
Cl9 C15 Cl7 110.1(3) . . ?
C16 C15 Cl8 110.9(4) . . ?
Cl9 C15 Cl8 108.1(3) . . ?
Cl7 C15 Cl8 108.5(3) . . ?
N3 C17 C18 111.0(4) . . ?
N3 C17 C21 108.8(4) . . ?
C18 C17 C21 112.0(4) . . ?
N3 C17 H6 108.3 . . ?
C18 C17 H6 108.3 . . ?
C21 C17 H6 108.3 . . ?
C13 C11 C12 59.8(4) . . ?
C13 C11 C10 116.8(6) . . ?
C12 C11 C10 116.8(5) . . ?
C13 C11 H8 117.0 . . ?
C12 C11 H8 117.0 . . ?
C10 C11 H8 117.0 . . ?
O6 C21 C17 111.2(5) . . ?
O6 C21 H9A 109.4 . . ?
C17 C21 H9A 109.4 . . ?
O6 C21 H9B 109.4 . . ?
C17 C21 H9B 109.4 . . ?
H9A C21 H9B 108.0 . . ?
O7 C23 N4 126.2(5) . . ?
O7 C23 C22 119.3(5) . . ?
N4 C23 C22 114.4(5) . . ?
C17 C18 C19 119.5(5) . . ?
C17 C18 C20 118.3(5) . . ?
C19 C18 C20 59.5(4) . . ?
C17 C18 H11 115.9 . . ?
C19 C18 H11 115.9 . . ?
C20 C18 H11 115.9 . . ?
C23 C22 Cl11 107.9(4) . . ?
C23 C22 Cl10 111.5(4) . . ?
Cl11 C22 Cl10 111.5(3) . . ?
C23 C22 Cl12 110.8(4) . . ?
Cl11 C22 Cl12 108.3(3) . . ?
Cl10 C22 Cl12 106.9(3) . . ?
O2 C7 C3 111.0(4) . . ?
O2 C7 H12A 109.4 . . ?
C3 C7 H12A 109.4 . . ?
O2 C7 H12B 109.4 . . ?
C3 C7 H12B 109.4 . . ?
H12A C7 H12B 108.0 . . ?
O4 C14 C10 111.5(5) . . ?
O4 C14 H13A 109.3 . . ?
C10 C14 H13A 109.3 . . ?
O4 C14 H13B 109.3 . . ?
C10 C14 H13B 109.3 . . ?
H13A C14 H13B 108.0 . . ?
N1 C3 C4 112.2(4) . . ?
N1 C3 C7 108.9(4) . . ?
C4 C3 C7 112.3(4) . . ?
N1 C3 H14 107.7 . . ?
C4 C3 H14 107.7 . . ?
C7 C3 H14 107.7 . . ?
C26 C25 C27 60.7(6) . . ?
C26 C25 C24 116.7(6) . . ?
C27 C25 C24 121.2(6) . . ?
C26 C25 H15 115.6 . . ?
C27 C25 H15 115.6 . . ?
C24 C25 H15 115.6 . . ?
C5 C4 C6 60.4(4) . . ?
C5 C4 C3 118.0(5) . . ?
C6 C4 C3 116.7(5) . . ?
C5 C4 H16 116.6 . . ?
C6 C4 H16 116.6 . . ?
C3 C4 H16 116.6 . . ?
O8 C28 C24 111.3(4) . . ?
O8 C28 H17A 109.4 . . ?
C24 C28 H17A 109.4 . . ?
O8 C28 H17B 109.4 . . ?
C24 C28 H17B 109.4 . . ?
H17A C28 H17B 108.0 . . ?
C4 C5 C6 60.3(4) . . ?
C4 C5 H18A 117.7 . . ?
C6 C5 H18A 117.7 . . ?
C4 C5 H18B 117.7 . . ?
C6 C5 H18B 117.7 . . ?
H18A C5 H18B 114.9 . . ?
O1 C2 N1 127.2(6) . . ?
O1 C2 C1 115.0(5) . . ?
N1 C2 C1 117.8(5) . . ?
C19 C20 C18 60.0(4) . . ?
C19 C20 H20A 117.8 . . ?
C18 C20 H20A 117.8 . . ?
C19 C20 H20B 117.8 . . ?
C18 C20 H20B 117.8 . . ?
H20A C20 H20B 114.9 . . ?
C13 C12 C11 59.9(4) . . ?
C13 C12 H21A 117.8 . . ?
C11 C12 H21A 117.8 . . ?
C13 C12 H21B 117.8 . . ?
C11 C12 H21B 117.8 . . ?
H21A C12 H21B 114.9 . . ?
C20 C19 C18 60.5(4) . . ?
C20 C19 H23A 117.7 . . ?
C18 C19 H23A 117.7 . . ?
C20 C19 H23B 117.7 . . ?
C18 C19 H23B 117.7 . . ?
H23A C19 H23B 114.8 . . ?
C12 C13 C11 60.4(4) . . ?
C12 C13 H25A 117.7 . . ?
C11 C13 H25A 117.7 . . ?
C12 C13 H25B 117.7 . . ?
C11 C13 H25B 117.7 . . ?
H25A C13 H25B 114.9 . . ?
C25 C26 C27 59.8(5) . . ?
C25 C26 H26A 117.8 . . ?
C27 C26 H26A 117.8 . . ?
C25 C26 H26B 117.8 . . ?
C27 C26 H26B 117.8 . . ?
H26A C26 H26B 114.9 . . ?
C25 C27 C26 59.5(5) . . ?
C25 C27 H27A 117.8 . . ?
C26 C27 H27A 117.8 . . ?
C25 C27 H27B 117.8 . . ?
C26 C27 H27B 117.8 . . ?
H27A C27 H27B 115.0 . . ?
C4 C6 C5 59.3(4) . . ?
C4 C6 H10A 117.8 . . ?
C5 C6 H10A 117.8 . . ?
C4 C6 H10B 117.8 . . ?
C5 C6 H10B 117.8 . . ?
H10A C6 H10B 115.0 . . ?

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
C23 N4 C24 C25 113.0(6) . . . . ?
C23 N4 C24 C28 -123.9(6) . . . . ?
C9 N2 C10 C11 121.8(5) . . . . ?
C9 N2 C10 C14 -112.4(5) . . . . ?
C17 N3 C16 O5 6.1(9) . . . . ?
C17 N3 C16 C15 -171.6(5) . . . . ?
C10 N2 C9 O3 -4.3(8) . . . . ?
C10 N2 C9 C8 173.1(4) . . . . ?
Cl4 C8 C9 O3 -46.8(6) . . . . ?
Cl6 C8 C9 O3 -170.2(4) . . . . ?
Cl5 C8 C9 O3 70.9(6) . . . . ?
Cl4 C8 C9 N2 135.5(4) . . . . ?
Cl6 C8 C9 N2 12.2(6) . . . . ?
Cl5 C8 C9 N2 -106.7(5) . . . . ?
O5 C16 C15 Cl9 11.0(6) . . . . ?
N3 C16 C15 Cl9 -171.0(4) . . . . ?
O5 C16 C15 Cl7 -109.8(5) . . . . ?
N3 C16 C15 Cl7 68.1(5) . . . . ?
O5 C16 C15 Cl8 131.7(4) . . . . ?
N3 C16 C15 Cl8 -50.4(5) . . . . ?
C16 N3 C17 C18 -117.9(6) . . . . ?
C16 N3 C17 C21 118.5(5) . . . . ?
N2 C10 C11 C13 -77.4(6) . . . . ?
C14 C10 C11 C13 159.0(5) . . . . ?
N2 C10 C11 C12 -145.3(6) . . . . ?
C14 C10 C11 C12 91.1(7) . . . . ?
N3 C17 C21 O6 -65.7(5) . . . . ?
C18 C17 C21 O6 171.3(4) . . . . ?
C24 N4 C23 O7 -5.2(9) . . . . ?
C24 N4 C23 C22 173.6(5) . . . . ?
N3 C17 C18 C19 80.0(6) . . . . ?
C21 C17 C18 C19 -158.2(5) . . . . ?
N3 C17 C18 C20 149.0(5) . . . . ?
C21 C17 C18 C20 -89.2(6) . . . . ?
O7 C23 C22 Cl11 110.3(5) . . . . ?
N4 C23 C22 Cl11 -68.6(6) . . . . ?
O7 C23 C22 Cl10 -12.5(7) . . . . ?
N4 C23 C22 Cl10 168.7(4) . . . . ?
O7 C23 C22 Cl12 -131.4(5) . . . . ?
N4 C23 C22 Cl12 49.8(6) . . . . ?
N2 C10 C14 O4 65.3(6) . . . . ?
C11 C10 C14 O4 -170.0(4) . . . . ?
C2 N1 C3 C4 -128.1(5) . . . . ?
C2 N1 C3 C7 106.9(6) . . . . ?
O2 C7 C3 N1 -57.0(6) . . . . ?
O2 C7 C3 C4 178.1(5) . . . . ?
N4 C24 C25 C26 -161.6(6) . . . . ?
C28 C24 C25 C26 77.5(7) . . . . ?
N4 C24 C25 C27 -91.1(7) . . . . ?
C28 C24 C25 C27 148.0(7) . . . . ?
N1 C3 C4 C5 140.5(5) . . . . ?
C7 C3 C4 C5 -96.4(6) . . . . ?
N1 C3 C4 C6 71.5(6) . . . . ?
C7 C3 C4 C6 -165.4(5) . . . . ?
N4 C24 C28 O8 66.7(6) . . . . ?
C25 C24 C28 O8 -171.1(5) . . . . ?
C3 C4 C5 C6 -106.4(6) . . . . ?
C3 N1 C2 O1 4.9(10) . . . . ?
C3 N1 C2 C1 -175.0(5) . . . . ?
Cl2 C1 C2 O1 67.2(7) . . . . ?
Cl3 C1 C2 O1 -165.5(6) . . . . ?
Cl1 C1 C2 O1 -49.3(7) . . . . ?
Cl2 C1 C2 N1 -112.9(6) . . . . ?
Cl3 C1 C2 N1 14.4(8) . . . . ?
Cl1 C1 C2 N1 130.6(5) . . . . ?
C17 C18 C20 C19 -109.4(6) . . . . ?
C10 C11 C12 C13 106.8(7) . . . . ?
C17 C18 C19 C20 107.3(6) . . . . ?
C10 C11 C13 C12 -106.9(6) . . . . ?
C24 C25 C26 C27 112.5(7) . . . . ?
C24 C25 C27 C26 -105.3(7) . . . . ?
C3 C4 C6 C5 108.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         3.756
_refine_diff_density_min         -1.540
_refine_diff_density_rms         0.141
