# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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_zh-iii-71
_database_code_depnum_ccdc_archive 'CCDC 2091559'
loop_
_audit_author_name
_audit_author_address
'Richard Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2022-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-05-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 N4, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C18.25 H14.50 Cl0.50 N4'
_chemical_formula_weight         307.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H14N4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0603(3)
_cell_length_b                   12.4451(3)
_cell_length_c                   14.3291(5)
_cell_angle_alpha                67.463(2)
_cell_angle_beta                 77.461(3)
_cell_angle_gamma                81.987(2)
_cell_volume                     1453.89(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6716
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5540
_cell_measurement_theta_min      3.8380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.90a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             642
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0294
0 -1 -1 0.0257
-1 -1 1 0.0443
1 1 -1 0.0742
1 -1 -2 0.0467
0 -1 2 0.0299
0 1 -2 0.0656
-2 0 -1 0.0665
-1 -1 -2 0.0538
-1 1 -1 0.0611
1 -1 1 0.0569
-2 1 1 0.0580
1 -2 0 0.0500
-1 2 1 0.0501
0 1 0 0.0651
1 1 2 0.0535
0 -1 0 0.0326
0 0 -1 0.0511

_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.055
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0006 0.9995 0.9969 -0.0399 -0.1324 -0.0353
-0.0006 -0.9995 -0.9969 0.0399 0.1324 0.0353
-0.9996 -0.9992 1.0041 0.0220 -0.0857 0.2662
0.9996 0.9992 -1.0041 -0.0220 0.0857 -0.2662
0.9989 -0.9995 -1.9979 -0.0112 0.2898 -0.1211
0.0009 -0.9985 2.0032 -0.1670 -0.0497 0.2588
-0.0009 0.9985 -2.0032 0.1670 0.0497 -0.2588
-2.0004 -0.0011 -0.9982 0.3090 -0.1328 0.0893
-1.0010 -1.0002 -1.9961 0.2289 0.0963 0.0426
-1.0003 0.9985 -1.0022 0.2180 -0.1077 -0.1024
1.0003 -0.9985 1.0022 -0.2180 0.1077 0.1024
-1.9993 0.9988 0.9988 0.2001 -0.3258 0.1285
0.9998 -1.9980 0.0053 -0.1781 0.2401 0.1377
-0.9993 1.9983 0.9948 0.1092 -0.3008 -0.0632
0.0001 0.9992 -0.0031 0.0291 -0.0717 -0.1098
1.0010 1.0002 1.9961 -0.2289 -0.0963 -0.0426
-0.0001 -0.9992 0.0031 -0.0291 0.0717 0.1098
-0.0005 -0.0004 -1.0000 0.0690 0.0607 -0.0745

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20746
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.752
_diffrn_reflns_theta_min         3.394
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  21.00   0.50    3.08    --   47.45 -68.00 -25.00   86
  2  ω     23.00  59.00   0.50    3.08    --   47.45 -68.00 -25.00   72
  3  ω     47.00  73.00   0.50   12.32    --  107.75 -68.00 -25.00   52
  4  ω     79.00 104.00   0.50   12.32    --  107.75 -77.00 -60.00   50
  5  ω     63.00 102.00   0.50   12.32    --  107.75 -94.00 -30.00   78
  6  ω     68.00 105.00   0.50   12.32    --  107.75-105.00  33.01   74
  7  ω     76.00 102.00   0.50   12.32    --  107.75 -94.00  60.00   52
  8  ω     59.00 104.00   0.50   12.32    --  107.75-101.00 141.87   90
  9  ω     51.00  78.00   0.50   12.32    --  107.75 -77.00 150.00   54
 10  ω     36.00 101.00   0.50   12.32    --  107.75 -94.00  90.00  130
 11  ω     37.00  68.00   0.50   12.32    --  107.75 -61.00 120.00   62
 12  ω     41.00  70.00   0.50   12.32    --  107.75 -94.00 120.00   58
 13  ω     36.00  63.00   0.50   12.32    --  107.75 -94.00  60.00   54
 14  ω     35.00  65.00   0.50   12.32    --  107.75 -61.00  30.00   60
 15  ω     36.00  61.00   0.50   12.32    --  107.75 -94.00   0.00   50
 16  ω     53.00 104.00   0.50   12.32    --  107.75 -94.00 -60.00  102
 17  ω     80.00 106.00   0.50   12.32    --  107.75-125.00-120.00   52
 18  ω     74.00 104.00   0.50   12.32    --  107.75 -94.00-180.00   60
 19  ω     72.00  98.00   0.50   12.32    --  107.75 -94.00-150.00   52
 20  ω     42.00  89.00   0.50   12.32    --  107.75 -94.00 -90.00   94
 21  ω     51.00  77.00   0.50   12.32    --  107.75-125.00-120.00   52
 22  ω     36.00 108.00   0.50   12.32    --  107.75-125.00-150.00  144
 23  ω     38.00 103.00   0.50   12.32    --  107.75 -94.00-120.00  130
 24  ω     36.00  69.00   0.50   12.32    --  107.75 -61.00 -90.00   66
 25  ω     38.00  68.00   0.50   12.32    --  107.75 -61.00 -60.00   60
 26  ω     37.00  90.00   0.50   12.32    --  107.75 -94.00  30.00  106
 27  ω    123.00 176.00   0.50   12.32    --  107.75  45.00 -60.00  106
 28  ω    132.00 158.00   0.50   12.32    --  107.75  61.00 -30.00   52
 29  ω    127.00 157.00   0.50   12.32    --  107.75  61.00 -90.00   60
 30  ω    122.00 171.00   0.50   12.32    --  107.75  45.00-120.00   98
 31  ω    124.00 167.00   0.50   12.32    --  107.75  45.00-180.00   86
 32  ω    108.00 135.00   0.50   12.32    --  107.75 125.00-180.00   54
 33  ω    110.00 159.00   0.50   12.32    --  107.75 125.00 -30.00   98
 34  ω    126.00 166.00   0.50   12.32    --  107.75  77.00  30.00   80
 35  ω    122.00 159.00   0.50   12.32    --  107.75  45.00  30.00   74
 36  ω    122.00 173.00   0.50   12.32    --  107.75  45.00  90.00  102
 37  ω    127.00 174.00   0.50   12.32    --  107.75  61.00 150.00   94
 38  ω    107.00 149.00   0.50   12.32    --  107.75 125.00  30.00   84
 39  ω    122.00 156.00   0.50   12.32    --  107.75  45.00   0.00   68
 40  ω     90.00 172.00   0.50   12.32    --  107.75  68.00 107.00  164
 41  ω     61.00 109.00   0.50    3.08    --   47.45  68.00 107.00   96
 42  ω    -24.00   2.00   0.50    3.08    --   47.45 -19.00  30.00   52
 43  ω    -52.00  17.00   0.50    3.08    --  -47.45  68.00 107.00  138
 44  ω    -55.00 -30.00   0.50    3.08    --  -47.45 125.00   0.00   50
 45  ω    -77.00 -25.00   0.50   12.32    --  -86.25  68.00 107.00  104
 46  ω   -113.00 -40.00   0.50    3.08    --  -47.45 -68.00 -25.00  146
 47  ω    -69.00 -28.00   0.50   12.32    --  -86.25  61.00 -90.00   82
 48  ω    -82.00 -57.00   0.50    3.08    --  -47.45 125.00-180.00   50
 49  ω    -80.00 -31.00   0.50    3.08    --  -47.45 125.00-120.00   98
 50  ω   -157.00-131.00   0.50   12.32    --  -86.25 -61.00 120.00   52
 51  ω   -159.00-134.00   0.50   12.32    --  -86.25 -61.00  30.00   50
 52  ω   -137.00-112.00   0.50   12.32    --  -86.25 -68.00 -25.00   50
 53  ω   -156.00-131.00   0.50   12.32    --  -86.25 -61.00 -90.00   50
 54  ω   -157.00-132.00   0.50   12.32    --  -86.25 -61.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1200848000
_diffrn_orient_matrix_UB_12      0.0288938000
_diffrn_orient_matrix_UB_13      -0.0689108000
_diffrn_orient_matrix_UB_21      0.0967000000
_diffrn_orient_matrix_UB_22      -0.0719520000
_diffrn_orient_matrix_UB_23      -0.0606959000
_diffrn_orient_matrix_UB_31      -0.0817863000
_diffrn_orient_matrix_UB_32      -0.1096396000
_diffrn_orient_matrix_UB_33      0.0745960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5252
_reflns_number_total             6019
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         6019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0768P)²+0.5743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          
;
The structure was refined by Least Squares using version 2018/2 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C36(0.5) H36A(0.5) H36B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C21(H21), C24(H24), C25(H25), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.89024(18) 0.71807(12) 0.53714(12) 0.0292(3) Uani 1 1 d . . . . .
N2 N 0.71672(18) 0.57787(12) 0.60608(11) 0.0281(3) Uani 1 1 d . . . . .
N3 N 0.69298(17) 0.45158(12) 0.52051(11) 0.0250(3) Uani 1 1 d . . . . .
N4 N 0.83686(18) 0.46071(13) 0.36356(12) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.911(3) 0.4957(19) 0.3111(18) 0.035 Uiso 1 1 d . U . . .
C1 C 0.9952(2) 0.77534(15) 0.46112(14) 0.0296(4) Uani 1 1 d . . . . .
H1 H 1.043337 0.832287 0.470983 0.036 Uiso 1 1 calc R U . . .
C2 C 1.0421(2) 0.75940(15) 0.36645(14) 0.0274(4) Uani 1 1 d . . . . .
C3 C 0.9794(2) 0.66842(14) 0.35785(14) 0.0269(4) Uani 1 1 d . . . . .
H3 H 1.009776 0.651055 0.297148 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8724(2) 0.60258(14) 0.43784(13) 0.0252(3) Uani 1 1 d . . . . .
C5 C 0.8070(2) 0.50441(14) 0.43270(13) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.6229(2) 0.35810(15) 0.52274(14) 0.0284(4) Uani 1 1 d . . . . .
H6 H 0.650831 0.332231 0.466594 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5166(2) 0.30336(15) 0.60227(14) 0.0300(4) Uani 1 1 d . . . . .
H7 H 0.470121 0.239997 0.601342 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4727(2) 0.33950(15) 0.68846(14) 0.0295(4) Uani 1 1 d . . . . .
C9 C 0.5414(2) 0.43122(15) 0.68597(13) 0.0297(4) Uani 1 1 d . . . . .
H9 H 0.513051 0.456703 0.742332 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6540(2) 0.49048(14) 0.60249(13) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.8257(2) 0.63266(14) 0.52581(13) 0.0266(4) Uani 1 1 d . . . . .
C12 C 1.1497(2) 0.83581(15) 0.28205(14) 0.0285(4) Uani 1 1 d . . . . .
C13 C 1.2300(2) 0.80241(16) 0.20123(15) 0.0305(4) Uani 1 1 d . . . . .
H13 H 1.216557 0.728155 0.201018 0.037 Uiso 1 1 calc R U . . .
C14 C 1.3284(2) 0.87548(18) 0.12180(16) 0.0361(4) Uani 1 1 d . . . . .
H14 H 1.381596 0.851009 0.067747 0.043 Uiso 1 1 calc R U . . .
C15 C 1.3503(2) 0.98466(18) 0.12035(17) 0.0382(4) Uani 1 1 d . . . . .
H15 H 1.418296 1.034696 0.065828 0.046 Uiso 1 1 calc R U . . .
C16 C 1.2713(2) 1.01949(17) 0.19977(17) 0.0368(4) Uani 1 1 d . . . . .
H16 H 1.285415 1.093785 0.199621 0.044 Uiso 1 1 calc R U . . .
C17 C 1.1724(2) 0.94651(16) 0.27896(16) 0.0338(4) Uani 1 1 d . . . . .
H17 H 1.118619 0.971813 0.332385 0.041 Uiso 1 1 calc R U . . .
C18 C 0.3561(2) 0.27674(16) 0.77742(15) 0.0352(4) Uani 1 1 d . . . . .
H18A H 0.341898 0.311277 0.830030 0.053 Uiso 1 1 calc R U . . .
H18B H 0.390035 0.194301 0.806391 0.053 Uiso 1 1 calc R U . . .
H18C H 0.260013 0.283488 0.754180 0.053 Uiso 1 1 calc R U . . .
N5 N 0.48226(17) 0.69480(12) 0.98795(11) 0.0255(3) Uani 1 1 d . . . . .
N6 N 0.64829(16) 0.54878(12) 1.06910(10) 0.0232(3) Uani 1 1 d . . . . .
N7 N 0.82958(16) 0.44907(11) 0.97644(10) 0.0219(3) Uani 1 1 d . . . . .
N8 N 0.85101(17) 0.48938(12) 0.80227(11) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.814(2) 0.5309(19) 0.7460(17) 0.030 Uiso 1 1 d . U . . .
C19 C 0.43182(19) 0.76301(14) 0.90338(13) 0.0252(3) Uani 1 1 d . . . . .
H19 H 0.348742 0.816824 0.910217 0.030 Uiso 1 1 calc R U . . .
C20 C 0.49025(19) 0.76309(13) 0.80385(13) 0.0232(3) Uani 1 1 d . . . . .
C21 C 0.60838(19) 0.68116(13) 0.79616(13) 0.0226(3) Uani 1 1 d . . . . .
H21 H 0.652000 0.676604 0.731112 0.027 Uiso 1 1 calc R U . . .
C22 C 0.66313(18) 0.60536(13) 0.88415(12) 0.0217(3) Uani 1 1 d . . . . .
C23 C 0.78388(18) 0.51505(13) 0.87958(12) 0.0217(3) Uani 1 1 d . . . . .
C24 C 0.9439(2) 0.36147(15) 0.98071(13) 0.0275(4) Uani 1 1 d . . . . .
H24 H 0.989833 0.348313 0.919474 0.033 Uiso 1 1 calc R U . . .
C25 C 0.9914(2) 0.29480(15) 1.06884(14) 0.0288(4) Uani 1 1 d . . . . .
H25 H 1.069798 0.235479 1.069105 0.035 Uiso 1 1 calc R U . . .
C26 C 0.9245(2) 0.31254(14) 1.16274(13) 0.0244(3) Uani 1 1 d . . . . .
C27 C 0.81280(19) 0.39822(14) 1.15803(13) 0.0237(3) Uani 1 1 d . . . . .
H27 H 0.767854 0.411347 1.219423 0.028 Uiso 1 1 calc R U . . .
C28 C 0.75936(19) 0.46961(13) 1.06561(12) 0.0218(3) Uani 1 1 d . . . . .
C29 C 0.42531(18) 0.84606(14) 0.71447(13) 0.0235(3) Uani 1 1 d . . . . .
C30 C 0.42218(19) 0.81745(14) 0.62980(13) 0.0251(3) Uani 1 1 d . . . . .
H30 H 0.465898 0.744215 0.627836 0.030 Uiso 1 1 calc R U . . .
C31 C 0.3558(2) 0.89489(14) 0.54823(13) 0.0264(4) Uani 1 1 d . . . . .
H31 H 0.354745 0.874007 0.491198 0.032 Uiso 1 1 calc R U . . .
C32 C 0.2912(2) 1.00229(14) 0.54941(14) 0.0281(4) Uani 1 1 d . . . . .
H32 H 0.244871 1.054597 0.494016 0.034 Uiso 1 1 calc R U . . .
C33 C 0.2952(2) 1.03231(14) 0.63268(14) 0.0287(4) Uani 1 1 d . . . . .
H33 H 0.251670 1.105785 0.634133 0.034 Uiso 1 1 calc R U . . .
C34 C 0.3621(2) 0.95596(14) 0.71349(14) 0.0266(4) Uani 1 1 d . . . . .
H34 H 0.365289 0.978305 0.769369 0.032 Uiso 1 1 calc R U . . .
C35 C 0.9760(2) 0.23716(15) 1.26162(13) 0.0277(4) Uani 1 1 d . . . . .
H35A H 0.931257 0.269314 1.314832 0.042 Uiso 1 1 calc R U . . .
H35B H 1.086745 0.234922 1.251721 0.042 Uiso 1 1 calc R U . . .
H35C H 0.943757 0.157996 1.282901 0.042 Uiso 1 1 calc R U . . .
C37 C 0.59980(18) 0.61621(13) 0.97951(12) 0.0219(3) Uani 1 1 d . . . . .
Cl1 Cl 1.09633(12) 1.01591(10) 0.90244(8) 0.0460(3) Uani 0.5 1 d . . P A -1
Cl2 Cl 0.87461(12) 0.91581(10) 1.08696(8) 0.0437(2) Uani 0.5 1 d . . P A -1
C36 C 0.9938(5) 1.0303(4) 1.0180(4) 0.0409(9) Uani 0.5 1 d . . P A -1
H36A H 1.065706 1.030991 1.060763 0.049 Uiso 0.5 1 calc R U P A -1
H36B H 0.932412 1.105376 1.001545 0.049 Uiso 0.5 1 calc R U P A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.320(3) . ?
N1 C11 1.358(2) . ?
N2 C10 1.318(2) . ?
N2 C11 1.363(2) . ?
N3 C5 1.440(2) . ?
N3 C6 1.388(2) . ?
N3 C10 1.395(2) . ?
N4 H4 0.91(2) . ?
N4 C5 1.267(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.412(2) . ?
C2 C3 1.391(2) . ?
C2 C12 1.478(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 C5 1.463(2) . ?
C4 C11 1.412(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.342(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.431(2) . ?
C8 C9 1.360(3) . ?
C8 C18 1.494(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.421(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.404(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N5 C19 1.320(2) . ?
N5 C37 1.360(2) . ?
N6 C28 1.314(2) . ?
N6 C37 1.364(2) . ?
N7 C23 1.433(2) . ?
N7 C24 1.388(2) . ?
N7 C28 1.398(2) . ?
N8 H8 0.88(2) . ?
N8 C23 1.274(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.409(2) . ?
C20 C21 1.388(2) . ?
C20 C29 1.482(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(2) . ?
C22 C23 1.465(2) . ?
C22 C37 1.412(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.342(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.436(2) . ?
C26 C27 1.356(2) . ?
C26 C35 1.501(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.426(2) . ?
C29 C30 1.396(2) . ?
C29 C34 1.403(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.389(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(2) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
Cl1 C36 1.775(5) . ?
Cl2 C36 1.749(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
C1 N1 C11 117.62(15) . . ?
C10 N2 C11 118.27(15) . . ?
C6 N3 C5 117.96(14) . . ?
C6 N3 C10 120.03(15) . . ?
C10 N3 C5 122.00(14) . . ?
C5 N4 H4 113.6(15) . . ?
N1 C1 H1 117.1 . . ?
N1 C1 C2 125.72(16) . . ?
C2 C1 H1 117.1 . . ?
C1 C2 C12 121.65(16) . . ?
C3 C2 C1 115.75(17) . . ?
C3 C2 C12 122.60(16) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.36(16) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 121.94(15) . . ?
C3 C4 C11 118.65(16) . . ?
C11 C4 C5 119.42(16) . . ?
N3 C5 C4 113.42(14) . . ?
N4 C5 N3 117.12(15) . . ?
N4 C5 C4 129.45(17) . . ?
N3 C6 H6 119.2 . . ?
C7 C6 N3 121.63(16) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.64(17) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C18 120.25(16) . . ?
C9 C8 C7 117.57(17) . . ?
C9 C8 C18 122.17(16) . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.68(16) . . ?
C10 C9 H9 118.7 . . ?
N2 C10 N3 123.38(16) . . ?
N2 C10 C9 119.18(15) . . ?
N3 C10 C9 117.44(15) . . ?
N1 C11 N2 114.93(15) . . ?
N1 C11 C4 121.60(17) . . ?
N2 C11 C4 123.46(16) . . ?
C13 C12 C2 121.75(16) . . ?
C13 C12 C17 117.49(17) . . ?
C17 C12 C2 120.75(16) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.21(16) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.53(18) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.10(19) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.32(17) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.35(17) . . ?
C16 C17 H17 119.3 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 N5 C37 117.74(14) . . ?
C28 N6 C37 117.71(14) . . ?
C24 N7 C23 118.40(14) . . ?
C24 N7 C28 120.16(14) . . ?
C28 N7 C23 121.43(14) . . ?
C23 N8 H8 112.8(14) . . ?
N5 C19 H19 117.1 . . ?
N5 C19 C20 125.79(16) . . ?
C20 C19 H19 117.1 . . ?
C19 C20 C29 120.57(15) . . ?
C21 C20 C19 116.10(15) . . ?
C21 C20 C29 123.32(15) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.00(15) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 121.54(14) . . ?
C21 C22 C37 118.99(15) . . ?
C37 C22 C23 119.47(15) . . ?
N7 C23 C22 113.62(14) . . ?
N8 C23 N7 117.71(15) . . ?
N8 C23 C22 128.67(15) . . ?
N7 C24 H24 119.0 . . ?
C25 C24 N7 121.91(16) . . ?
C25 C24 H24 119.0 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.46(16) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C35 120.58(15) . . ?
C27 C26 C25 117.32(16) . . ?
C27 C26 C35 122.10(16) . . ?
C26 C27 H27 118.3 . . ?
C26 C27 C28 123.35(15) . . ?
C28 C27 H27 118.3 . . ?
N6 C28 N7 124.28(15) . . ?
N6 C28 C27 118.92(15) . . ?
N7 C28 C27 116.80(15) . . ?
C30 C29 C20 121.65(14) . . ?
C30 C29 C34 117.80(15) . . ?
C34 C29 C20 120.54(15) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.81(15) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.63(16) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 119.10(16) . . ?
C33 C32 H32 120.5 . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.43(15) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 H34 119.4 . . ?
C33 C34 C29 121.22(16) . . ?
C33 C34 H34 119.4 . . ?
C26 C35 H35A 109.5 . . ?
C26 C35 H35B 109.5 . . ?
C26 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N5 C37 N6 115.26(14) . . ?
N5 C37 C22 121.29(15) . . ?
N6 C37 C22 123.43(15) . . ?
Cl1 C36 H36A 109.4 . . ?
Cl1 C36 H36B 109.4 . . ?
Cl2 C36 Cl1 111.1(2) . . ?
Cl2 C36 H36A 109.4 . . ?
Cl2 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?

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
N1 C1 C2 C3 -5.6(3) . . . . ?
N1 C1 C2 C12 173.86(16) . . . . ?
N3 C6 C7 C8 -0.5(3) . . . . ?
C1 N1 C11 N2 -179.07(15) . . . . ?
C1 N1 C11 C4 2.3(2) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
C1 C2 C12 C13 161.21(17) . . . . ?
C1 C2 C12 C17 -20.4(3) . . . . ?
C2 C3 C4 C5 -178.40(15) . . . . ?
C2 C3 C4 C11 2.0(2) . . . . ?
C2 C12 C13 C14 178.86(17) . . . . ?
C2 C12 C17 C16 -179.17(18) . . . . ?
C3 C2 C12 C13 -19.4(3) . . . . ?
C3 C2 C12 C17 159.03(17) . . . . ?
C3 C4 C5 N3 -176.95(14) . . . . ?
C3 C4 C5 N4 3.4(3) . . . . ?
C3 C4 C11 N1 -4.8(2) . . . . ?
C3 C4 C11 N2 176.73(15) . . . . ?
C5 N3 C6 C7 179.34(16) . . . . ?
C5 N3 C10 N2 0.4(2) . . . . ?
C5 N3 C10 C9 -179.19(14) . . . . ?
C5 C4 C11 N1 175.62(15) . . . . ?
C5 C4 C11 N2 -2.8(2) . . . . ?
C6 N3 C5 N4 -0.8(2) . . . . ?
C6 N3 C5 C4 179.51(14) . . . . ?
C6 N3 C10 N2 179.36(15) . . . . ?
C6 N3 C10 C9 -0.2(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C18 -178.97(17) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 N2 -179.29(16) . . . . ?
C8 C9 C10 N3 0.3(3) . . . . ?
C10 N2 C11 N1 -176.96(15) . . . . ?
C10 N2 C11 C4 1.6(2) . . . . ?
C10 N3 C5 N4 178.19(15) . . . . ?
C10 N3 C5 C4 -1.5(2) . . . . ?
C10 N3 C6 C7 0.3(2) . . . . ?
C11 N1 C1 C2 3.0(3) . . . . ?
C11 N2 C10 N3 -0.3(2) . . . . ?
C11 N2 C10 C9 179.24(15) . . . . ?
C11 C4 C5 N3 2.6(2) . . . . ?
C11 C4 C5 N4 -177.04(17) . . . . ?
C12 C2 C3 C4 -176.71(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C18 C8 C9 C10 179.04(16) . . . . ?
N5 C19 C20 C21 2.0(2) . . . . ?
N5 C19 C20 C29 -178.72(15) . . . . ?
N7 C24 C25 C26 -0.1(3) . . . . ?
C19 N5 C37 N6 179.39(14) . . . . ?
C19 N5 C37 C22 -1.8(2) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C19 C20 C29 C30 -148.35(16) . . . . ?
C19 C20 C29 C34 30.5(2) . . . . ?
C20 C21 C22 C23 177.77(14) . . . . ?
C20 C21 C22 C37 -2.0(2) . . . . ?
C20 C29 C30 C31 177.66(15) . . . . ?
C20 C29 C34 C33 -177.16(16) . . . . ?
C21 C20 C29 C30 30.8(2) . . . . ?
C21 C20 C29 C34 -150.34(16) . . . . ?
C21 C22 C23 N7 177.50(13) . . . . ?
C21 C22 C23 N8 -2.3(3) . . . . ?
C21 C22 C37 N5 3.2(2) . . . . ?
C21 C22 C37 N6 -178.06(14) . . . . ?
C23 N7 C24 C25 -179.02(15) . . . . ?
C23 N7 C28 N6 0.0(2) . . . . ?
C23 N7 C28 C27 179.46(13) . . . . ?
C23 C22 C37 N5 -176.53(14) . . . . ?
C23 C22 C37 N6 2.2(2) . . . . ?
C24 N7 C23 N8 0.1(2) . . . . ?
C24 N7 C23 C22 -179.72(14) . . . . ?
C24 N7 C28 N6 -178.48(15) . . . . ?
C24 N7 C28 C27 1.0(2) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C24 C25 C26 C35 179.22(16) . . . . ?
C25 C26 C27 C28 0.4(2) . . . . ?
C26 C27 C28 N6 178.54(15) . . . . ?
C26 C27 C28 N7 -0.9(2) . . . . ?
C28 N6 C37 N5 178.49(14) . . . . ?
C28 N6 C37 C22 -0.3(2) . . . . ?
C28 N7 C23 N8 -178.43(14) . . . . ?
C28 N7 C23 C22 1.8(2) . . . . ?
C28 N7 C24 C25 -0.5(3) . . . . ?
C29 C20 C21 C22 -179.68(14) . . . . ?
C29 C30 C31 C32 0.0(3) . . . . ?
C30 C29 C34 C33 1.7(3) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C32 C33 C34 C29 -1.0(3) . . . . ?
C34 C29 C30 C31 -1.2(2) . . . . ?
C35 C26 C27 C28 -178.66(15) . . . . ?
C37 N5 C19 C20 -0.9(2) . . . . ?
C37 N6 C28 N7 -0.9(2) . . . . ?
C37 N6 C28 C27 179.72(14) . . . . ?
C37 C22 C23 N7 -2.7(2) . . . . ?
C37 C22 C23 N8 177.48(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.618
