data_global

_publ_section_references
;
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R., Towler, M. (2004). 
J. Appl. Cryst., 37, 335--338.

Bruker (2018). Apex3 v2018.1-0, SAINT V8.38A, Bruker AXS 
Inc.: Madison (WI), USA, 2018.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. 
(2009), J. Appl. Cryst. 42, 339-341.

Hübschle, C. B., Sheldrick, G. M. and Dittrich, B. (2011). J. Appl. Cryst., 
44, 1281--1284.

Sheldrick, G.M. (2008). Acta Cryst., A64, 112--122.

Sheldrick, G. M. (2018). SHELXL2018. University of Göttingen, Germany.

Sheldrick G. M. (2015). "Crystal structure refinement with SHELXL", Acta Cryst., 
C71, 3-8.

Sheldrick, G. M. (2012). TWINABS. Ver. 2012/1. (Sheldrick, 2012)

Spek, A. L. (2003). J. Appl. Cryst., 36, 7--13.

CSD: Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed., 53, 662--671.

Publcif: Westrip, S. P. (2010). J. Appl. Cryst., 43, 920--925.
;

data_cx0501
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 '2(C8 Cl2 N2 O2), C12 H28 N, Cl'
_chemical_formula_sum
 'C28 H28 Cl5 N5 O4' 
_chemical_formula_weight          675.80

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    15.2745(13)
_cell_length_b                    10.2019(9)
_cell_length_c                    20.6506(18)
_cell_angle_alpha                 90
_cell_angle_beta                  96.098(6)
_cell_angle_gamma                 90
_cell_volume                      3199.8(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     8348
_cell_measurement_theta_min       2.682
_cell_measurement_theta_max       29.273
 
_exptl_crystal_description        block
_exptl_crystal_colour             red
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.403          
_exptl_crystal_F_000              1392
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.218
_exptl_crystal_size_mid           0.102
_exptl_crystal_size_min           0.064
_exptl_absorpt_coefficient_mu     0.495
_shelx_estimated_absorpt_T_min    0.900
_shelx_estimated_absorpt_T_max    0.969
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6243
_exptl_absorpt_correction_T_max   0.7460
_exptl_absorpt_process_details    
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.8369.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method        'ω and φ scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             38981
_diffrn_reflns_av_unetI/netI      0.1252
_diffrn_reflns_av_R_equivalents   0.0978
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          3.026
_diffrn_reflns_theta_max          30.092
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.989
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.989
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.989
_diffrn_reflns_point_group_measured_fraction_full  0.995
_reflns_number_total              9320
_reflns_number_gt                 4835
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection        'APEX2 V2.1-4 (Bruker, 2007)'
_computing_cell_refinement        'SAINT V7.23A (Bruker, 2005)'
_computing_data_reduction         'SAINT V7.23A (Bruker, 2005)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement 
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
Olex2 (Dolomanov et al., 2009)
SHELXLE Rev946 (Hübschle et al., 2011)
; 
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           
;
The ring involving O1A and O2A is disordered by a pseudo-mirror 
operation, swapping the Cl atoms with the cyano groups. The two 
disordered moieties were restrained to have similar geometries. 
Uij components of ADPs for disordered atoms closer to each other 
than 2.0 Angstrom were restrained to be similar and the ADPs of 
oxygen atoms O1A and O1B, and of O2A and O2B were each constrained
to be identical. Subject to these conditions the occupancy ratio 
refined to 0.844(3) to 0.156(3). 
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0429P)²+0.2478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          9320
_refine_ls_number_parameters      498
_refine_ls_number_restraints      424
_refine_ls_R_factor_all           0.1531
_refine_ls_R_factor_gt            0.0613
_refine_ls_wR_factor_ref          0.1201
_refine_ls_wR_factor_gt           0.0978
_refine_ls_goodness_of_fit_ref    0.996
_refine_ls_restrained_S_all       0.981
_refine_ls_shift/su_max           0.001
_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_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 0.74270(4) 0.17681(7) 0.32954(3) 0.03204(18) Uani 1 1 d . . . . .
Cl2 Cl 0.95221(4) 0.16428(7) 0.36079(3) 0.03187(18) Uani 1 1 d . . . . .
O1 O 1.00373(12) 0.14233(16) 0.49998(8) 0.0258(4) Uani 1 1 d . . . . .
O2 O 0.65866(11) 0.12114(17) 0.44829(8) 0.0248(4) Uani 1 1 d . . . . .
N1 N 0.94345(17) 0.1502(3) 0.65719(12) 0.0436(7) Uani 1 1 d . . . . .
N2 N 0.67381(16) 0.1776(2) 0.61773(12) 0.0376(6) Uani 1 1 d . . . . .
C1 C 0.79426(16) 0.1682(2) 0.40667(11) 0.0216(6) Uani 1 1 d . . . . .
C2 C 0.88209(16) 0.1629(2) 0.41981(12) 0.0219(6) Uani 1 1 d . . . . .
C3 C 0.92483(17) 0.1534(2) 0.48742(12) 0.0198(6) Uani 1 1 d . . . . .
C4 C 0.86570(16) 0.1591(2) 0.54035(11) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.77763(16) 0.1660(2) 0.52724(11) 0.0193(5) Uani 1 1 d . . . . .
C6 C 0.73491(16) 0.1535(2) 0.45885(12) 0.0196(6) Uani 1 1 d . . . . .
C7 C 0.90890(17) 0.1552(3) 0.60573(13) 0.0262(6) Uani 1 1 d . . . . .
C8 C 0.71944(17) 0.1717(3) 0.57753(13) 0.0254(6) Uani 1 1 d . . . . .
Cl1A Cl 0.86598(9) 0.51105(12) 0.32890(6) 0.0365(4) Uani 0.844(3) 1 d D U P A 1
Cl2A Cl 0.80636(9) 0.81020(12) 0.33150(6) 0.0405(4) Uani 0.844(3) 1 d D U P A 1
O1A O 0.7896(3) 0.8954(3) 0.46303(13) 0.0339(8) Uani 0.844(3) 1 d D U P A 1
O2A O 0.9281(2) 0.4212(3) 0.45988(12) 0.0225(7) Uani 0.844(3) 1 d D U P A 1
N1A N 0.8116(4) 0.8302(5) 0.6285(3) 0.0461(14) Uani 0.844(3) 1 d D U P A 1
N2A N 0.9101(4) 0.4549(4) 0.6276(3) 0.0372(12) Uani 0.844(3) 1 d D U P A 1
C1A C 0.8573(3) 0.5929(4) 0.39910(17) 0.0237(9) Uani 0.844(3) 1 d D U P A 1
C2A C 0.8315(3) 0.7180(4) 0.39997(17) 0.0248(9) Uani 0.844(3) 1 d D U P A 1
C3A C 0.8188(3) 0.7850(4) 0.46181(18) 0.0253(9) Uani 0.844(3) 1 d D U P A 1
C4A C 0.8403(3) 0.7112(4) 0.52259(17) 0.0223(8) Uani 0.844(3) 1 d D U P A 1
C5A C 0.8688(3) 0.5867(4) 0.52199(16) 0.0213(8) Uani 0.844(3) 1 d D U P A 1
C6A C 0.8859(3) 0.5209(4) 0.45972(16) 0.0195(8) Uani 0.844(3) 1 d D U P A 1
C7A C 0.8257(3) 0.7765(5) 0.5812(2) 0.0310(11) Uani 0.844(3) 1 d D U P A 1
C8A C 0.8909(3) 0.5132(5) 0.5799(2) 0.0255(10) Uani 0.844(3) 1 d D U P A 1
Cl1B Cl 0.8983(6) 0.5015(9) 0.6117(5) 0.0342(19) Uani 0.156(3) 1 d D U P A 2
Cl2B Cl 0.8254(7) 0.7896(9) 0.6139(5) 0.038(2) Uani 0.156(3) 1 d D U P A 2
O1B O 0.7886(18) 0.897(2) 0.4862(10) 0.0339(8) Uani 0.156(3) 1 d D U P A 2
O2B O 0.9270(16) 0.420(2) 0.4812(9) 0.0225(7) Uani 0.156(3) 1 d D U P A 2
N1B N 0.7949(19) 0.853(2) 0.3180(11) 0.044(4) Uani 0.156(3) 1 d D U P A 2
N2B N 0.8596(17) 0.463(2) 0.3148(10) 0.037(4) Uani 0.156(3) 1 d D U P A 2
C1B C 0.872(2) 0.587(2) 0.5424(8) 0.023(2) Uani 0.156(3) 1 d D U P A 2
C2B C 0.842(2) 0.711(2) 0.5430(8) 0.025(2) Uani 0.156(3) 1 d D U P A 2
C3B C 0.819(2) 0.785(2) 0.4833(8) 0.026(2) Uani 0.156(3) 1 d D U P A 2
C4B C 0.827(2) 0.718(2) 0.4214(8) 0.025(2) Uani 0.156(3) 1 d D U P A 2
C5B C 0.855(2) 0.593(2) 0.4197(8) 0.023(2) Uani 0.156(3) 1 d D U P A 2
C6B C 0.8827(18) 0.519(2) 0.4812(8) 0.021(2) Uani 0.156(3) 1 d D U P A 2
C7B C 0.8041(14) 0.793(2) 0.3646(9) 0.032(3) Uani 0.156(3) 1 d D U P A 2
C8B C 0.8535(13) 0.5178(19) 0.3627(8) 0.028(3) Uani 0.156(3) 1 d D U P A 2
N3 N 0.44616(13) 0.3403(2) 0.36039(9) 0.0209(5) Uani 1 1 d . . . . .
C9 C 0.41321(16) 0.3172(3) 0.42622(11) 0.0218(6) Uani 1 1 d . . . . .
H9A H 0.382825 0.397536 0.438761 0.026 Uiso 1 1 calc R U . . .
H9B H 0.369001 0.245898 0.421580 0.026 Uiso 1 1 calc R U . . .
C10 C 0.48301(16) 0.2816(3) 0.48102(11) 0.0256(6) Uani 1 1 d . . . . .
H10A H 0.517542 0.360421 0.495475 0.031 Uiso 1 1 calc R U . . .
H10B H 0.523745 0.215730 0.465758 0.031 Uiso 1 1 calc R U . . .
C11 C 0.43798(18) 0.2261(3) 0.53734(12) 0.0313(7) Uani 1 1 d . . . . .
H11A H 0.409356 0.142979 0.524105 0.047 Uiso 1 1 calc R U . . .
H11B H 0.393689 0.288501 0.549415 0.047 Uiso 1 1 calc R U . . .
H11C H 0.481903 0.211239 0.574766 0.047 Uiso 1 1 calc R U . . .
C12 C 0.49215(16) 0.2206(3) 0.33709(12) 0.0241(6) Uani 1 1 d . . . . .
H12A H 0.552122 0.217065 0.360504 0.029 Uiso 1 1 calc R U . . .
H12B H 0.498658 0.232390 0.290258 0.029 Uiso 1 1 calc R U . . .
C13 C 0.44784(17) 0.0893(3) 0.34558(12) 0.0269(6) Uani 1 1 d . . . . .
H13A H 0.384693 0.094852 0.329050 0.032 Uiso 1 1 calc R U . . .
H13B H 0.452318 0.065922 0.392336 0.032 Uiso 1 1 calc R U . . .
C14 C 0.49289(18) -0.0152(3) 0.30796(13) 0.0334(7) Uani 1 1 d . . . . .
H14A H 0.488104 0.008458 0.261724 0.050 Uiso 1 1 calc R U . . .
H14B H 0.464352 -0.100034 0.313034 0.050 Uiso 1 1 calc R U . . .
H14C H 0.555149 -0.021039 0.324972 0.050 Uiso 1 1 calc R U . . .
C15 C 0.36646(16) 0.3711(3) 0.31163(12) 0.0235(6) Uani 1 1 d . . . . .
H15A H 0.386241 0.374139 0.267526 0.028 Uiso 1 1 calc R U . . .
H15B H 0.324071 0.297765 0.312193 0.028 Uiso 1 1 calc R U . . .
C16 C 0.31878(18) 0.4965(3) 0.32270(13) 0.0324(7) Uani 1 1 d . . . . .
H16A H 0.359624 0.571603 0.321585 0.039 Uiso 1 1 calc R U . . .
H16B H 0.296592 0.494579 0.366026 0.039 Uiso 1 1 calc R U . . .
C17 C 0.24218(19) 0.5124(3) 0.26987(13) 0.0403(8) Uani 1 1 d . . . . .
H17A H 0.264496 0.513922 0.227098 0.060 Uiso 1 1 calc R U . . .
H17B H 0.211387 0.594747 0.276642 0.060 Uiso 1 1 calc R U . . .
H17C H 0.201309 0.438813 0.271822 0.060 Uiso 1 1 calc R U . . .
C18 C 0.51094(17) 0.4538(3) 0.36539(12) 0.0252(6) Uani 1 1 d . . . . .
H18A H 0.481578 0.531298 0.382195 0.030 Uiso 1 1 calc R U . . .
H18B H 0.561118 0.430709 0.397735 0.030 Uiso 1 1 calc R U . . .
C19 C 0.54674(19) 0.4915(3) 0.30220(13) 0.0360(7) Uani 1 1 d . . . . .
H19A H 0.575493 0.414646 0.284250 0.043 Uiso 1 1 calc R U . . .
H19B H 0.497695 0.519563 0.269962 0.043 Uiso 1 1 calc R U . . .
C20 C 0.61267(19) 0.6020(3) 0.31392(13) 0.0376(8) Uani 1 1 d . . . . .
H20A H 0.639431 0.619834 0.273753 0.056 Uiso 1 1 calc R U . . .
H20B H 0.658615 0.576694 0.348419 0.056 Uiso 1 1 calc R U . . .
H20C H 0.582649 0.680911 0.327179 0.056 Uiso 1 1 calc R U . . .
Cl3 Cl 0.71422(4) 0.43434(6) 0.47839(3) 0.02293(16) Uani 1 1 d . . . . .
 
 
_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 1.702(2) . ?
Cl2 C2 1.706(2) . ?
O1 C3 1.211(3) . ?
O2 C6 1.208(3) . ?
N1 C7 1.136(3) . ?
N2 C8 1.141(3) . ?
C1 C2 1.341(3) . ?
C1 C6 1.488(3) . ?
C2 C3 1.480(3) . ?
C3 C4 1.491(3) . ?
C4 C5 1.346(3) . ?
C4 C7 1.439(4) . ?
C5 C8 1.438(4) . ?
C5 C6 1.497(3) . ?
Cl1A C1A 1.690(4) . ?
Cl2A C2A 1.708(4) . ?
O1A C3A 1.213(4) . ?
O2A C6A 1.204(4) . ?
N1A C7A 1.159(7) . ?
N2A C8A 1.162(7) . ?
C1A C2A 1.336(5) . ?
C1A C6A 1.477(5) . ?
C2A C3A 1.479(5) . ?
C3A C4A 1.471(5) . ?
C4A C5A 1.342(5) . ?
C4A C7A 1.420(6) . ?
C5A C8A 1.421(5) . ?
C5A C6A 1.498(4) . ?
Cl1B C1B 1.689(16) . ?
Cl2B C2B 1.711(16) . ?
O1B C3B 1.236(15) . ?
O2B C6B 1.215(15) . ?
N1B C7B 1.137(17) . ?
N2B C8B 1.149(16) . ?
C1B C2B 1.341(17) . ?
C1B C6B 1.468(16) . ?
C2B C3B 1.457(16) . ?
C3B C4B 1.466(16) . ?
C4B C5B 1.346(17) . ?
C4B C7B 1.410(16) . ?
C5B C8B 1.404(16) . ?
C5B C6B 1.499(16) . ?
N3 C12 1.512(3) . ?
N3 C9 1.517(3) . ?
N3 C18 1.520(3) . ?
N3 C15 1.528(3) . ?
C9 C10 1.514(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.519(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.502(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.521(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.517(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.513(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C1 C6 121.5(2) . . ?
C2 C1 Cl1 123.01(19) . . ?
C6 C1 Cl1 115.21(18) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C2 Cl2 123.1(2) . . ?
C3 C2 Cl2 115.27(19) . . ?
O1 C3 C2 122.5(2) . . ?
O1 C3 C4 120.9(2) . . ?
C2 C3 C4 116.6(2) . . ?
C5 C4 C7 122.6(2) . . ?
C5 C4 C3 121.7(2) . . ?
C7 C4 C3 115.7(2) . . ?
C4 C5 C8 122.6(2) . . ?
C4 C5 C6 120.8(2) . . ?
C8 C5 C6 116.4(2) . . ?
O2 C6 C1 123.2(2) . . ?
O2 C6 C5 120.6(2) . . ?
C1 C6 C5 115.9(2) . . ?
N1 C7 C4 178.9(3) . . ?
N2 C8 C5 179.1(3) . . ?
C2A C1A C6A 121.7(3) . . ?
C2A C1A Cl1A 122.2(3) . . ?
C6A C1A Cl1A 116.0(3) . . ?
C1A C2A C3A 121.2(3) . . ?
C1A C2A Cl2A 123.8(3) . . ?
C3A C2A Cl2A 114.9(3) . . ?
O1A C3A C4A 120.5(3) . . ?
O1A C3A C2A 122.0(3) . . ?
C4A C3A C2A 117.5(3) . . ?
C5A C4A C7A 122.1(4) . . ?
C5A C4A C3A 121.3(3) . . ?
C7A C4A C3A 116.5(3) . . ?
C4A C5A C8A 122.7(3) . . ?
C4A C5A C6A 121.2(3) . . ?
C8A C5A C6A 116.0(3) . . ?
O2A C6A C1A 122.2(3) . . ?
O2A C6A C5A 121.2(3) . . ?
C1A C6A C5A 116.2(3) . . ?
N1A C7A C4A 178.3(6) . . ?
N2A C8A C5A 178.8(6) . . ?
C2B C1B C6B 121.6(14) . . ?
C2B C1B Cl1B 122.0(13) . . ?
C6B C1B Cl1B 116.5(13) . . ?
C1B C2B C3B 122.1(15) . . ?
C1B C2B Cl2B 122.1(13) . . ?
C3B C2B Cl2B 115.8(13) . . ?
O1B C3B C2B 119.8(16) . . ?
O1B C3B C4B 122.5(16) . . ?
C2B C3B C4B 117.5(14) . . ?
C5B C4B C7B 122.8(16) . . ?
C5B C4B C3B 121.2(14) . . ?
C7B C4B C3B 116.0(15) . . ?
C4B C5B C8B 124.2(16) . . ?
C4B C5B C6B 121.2(14) . . ?
C8B C5B C6B 114.3(15) . . ?
O2B C6B C1B 120.5(16) . . ?
O2B C6B C5B 121.8(16) . . ?
C1B C6B C5B 116.2(13) . . ?
N1B C7B C4B 173(3) . . ?
N2B C8B C5B 173(3) . . ?
C12 N3 C9 111.68(19) . . ?
C12 N3 C18 108.39(19) . . ?
C9 N3 C18 109.45(18) . . ?
C12 N3 C15 108.71(18) . . ?
C9 N3 C15 107.79(18) . . ?
C18 N3 C15 110.83(19) . . ?
C10 C9 N3 115.63(19) . . ?
C10 C9 H9A 108.4 . . ?
N3 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
N3 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 108.7(2) . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 116.6(2) . . ?
N3 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
N3 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C12 C13 C14 109.1(2) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N3 116.1(2) . . ?
C16 C15 H15A 108.3 . . ?
N3 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
N3 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 C17 109.3(2) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N3 115.3(2) . . ?
C19 C18 H18A 108.5 . . ?
N3 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
N3 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 110.2(2) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 C1 C2 C3 -5.2(4) . . . . ?
Cl1 C1 C2 C3 -179.04(19) . . . . ?
C6 C1 C2 Cl2 173.83(19) . . . . ?
Cl1 C1 C2 Cl2 0.0(3) . . . . ?
C1 C2 C3 O1 176.4(2) . . . . ?
Cl2 C2 C3 O1 -2.7(3) . . . . ?
C1 C2 C3 C4 -4.0(4) . . . . ?
Cl2 C2 C3 C4 176.88(17) . . . . ?
O1 C3 C4 C5 -177.2(2) . . . . ?
C2 C3 C4 C5 3.2(3) . . . . ?
O1 C3 C4 C7 2.1(3) . . . . ?
C2 C3 C4 C7 -177.5(2) . . . . ?
C7 C4 C5 C8 0.8(4) . . . . ?
C3 C4 C5 C8 -179.9(2) . . . . ?
C7 C4 C5 C6 -172.5(2) . . . . ?
C3 C4 C5 C6 6.7(4) . . . . ?
C2 C1 C6 O2 -158.6(2) . . . . ?
Cl1 C1 C6 O2 15.7(3) . . . . ?
C2 C1 C6 C5 14.6(3) . . . . ?
Cl1 C1 C6 C5 -171.13(18) . . . . ?
C4 C5 C6 O2 158.0(2) . . . . ?
C8 C5 C6 O2 -15.7(3) . . . . ?
C4 C5 C6 C1 -15.3(3) . . . . ?
C8 C5 C6 C1 171.0(2) . . . . ?
C6A C1A C2A C3A -8.5(7) . . . . ?
Cl1A C1A C2A C3A 176.0(4) . . . . ?
C6A C1A C2A Cl2A 174.4(4) . . . . ?
Cl1A C1A C2A Cl2A -1.1(7) . . . . ?
C1A C2A C3A O1A -174.8(5) . . . . ?
Cl2A C2A C3A O1A 2.6(7) . . . . ?
C1A C2A C3A C4A 3.4(7) . . . . ?
Cl2A C2A C3A C4A -179.3(4) . . . . ?
O1A C3A C4A C5A 176.8(5) . . . . ?
C2A C3A C4A C5A -1.3(7) . . . . ?
O1A C3A C4A C7A -0.5(7) . . . . ?
C2A C3A C4A C7A -178.6(5) . . . . ?
C7A C4A C5A C8A -3.5(8) . . . . ?
C3A C4A C5A C8A 179.4(5) . . . . ?
C7A C4A C5A C6A -178.5(5) . . . . ?
C3A C4A C5A C6A 4.4(7) . . . . ?
C2A C1A C6A O2A -162.1(5) . . . . ?
Cl1A C1A C6A O2A 13.7(6) . . . . ?
C2A C1A C6A C5A 10.9(7) . . . . ?
Cl1A C1A C6A C5A -173.2(4) . . . . ?
C4A C5A C6A O2A 164.3(5) . . . . ?
C8A C5A C6A O2A -11.0(7) . . . . ?
C4A C5A C6A C1A -8.8(7) . . . . ?
C8A C5A C6A C1A 175.8(4) . . . . ?
C6B C1B C2B C3B 0(5) . . . . ?
Cl1B C1B C2B C3B 180(3) . . . . ?
C6B C1B C2B Cl2B 178(3) . . . . ?
Cl1B C1B C2B Cl2B -3(5) . . . . ?
C1B C2B C3B O1B 176(3) . . . . ?
Cl2B C2B C3B O1B -1(4) . . . . ?
C1B C2B C3B C4B 2(5) . . . . ?
Cl2B C2B C3B C4B -176(3) . . . . ?
O1B C3B C4B C5B -175(3) . . . . ?
C2B C3B C4B C5B 0(5) . . . . ?
O1B C3B C4B C7B 5(5) . . . . ?
C2B C3B C4B C7B 180(3) . . . . ?
C7B C4B C5B C8B -9(5) . . . . ?
C3B C4B C5B C8B 172(3) . . . . ?
C7B C4B C5B C6B 177(3) . . . . ?
C3B C4B C5B C6B -2(5) . . . . ?
C2B C1B C6B O2B 163(3) . . . . ?
Cl1B C1B C6B O2B -16(4) . . . . ?
C2B C1B C6B C5B -3(5) . . . . ?
Cl1B C1B C6B C5B 177(2) . . . . ?
C4B C5B C6B O2B -162(3) . . . . ?
C8B C5B C6B O2B 23(4) . . . . ?
C4B C5B C6B C1B 4(4) . . . . ?
C8B C5B C6B C1B -170(3) . . . . ?
C12 N3 C9 C10 59.2(3) . . . . ?
C18 N3 C9 C10 -60.9(3) . . . . ?
C15 N3 C9 C10 178.5(2) . . . . ?
N3 C9 C10 C11 -164.7(2) . . . . ?
C9 N3 C12 C13 43.8(3) . . . . ?
C18 N3 C12 C13 164.5(2) . . . . ?
C15 N3 C12 C13 -75.0(3) . . . . ?
N3 C12 C13 C14 169.0(2) . . . . ?
C12 N3 C15 C16 -173.0(2) . . . . ?
C9 N3 C15 C16 65.8(3) . . . . ?
C18 N3 C15 C16 -54.0(3) . . . . ?
N3 C15 C16 C17 179.6(2) . . . . ?
C12 N3 C18 C19 60.3(3) . . . . ?
C9 N3 C18 C19 -177.7(2) . . . . ?
C15 N3 C18 C19 -58.9(3) . . . . ?
N3 C18 C19 C20 -178.0(2) . . . . ?
 
_refine_diff_density_max    0.430
_refine_diff_density_min   -0.306
_refine_diff_density_rms    0.077



