# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_d8v18362_0m
_database_code_depnum_ccdc_archive 'CCDC 1875033'
_audit_update_record             
;
2018-10-24 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H38 Cl2 N2'
_chemical_formula_weight         773.75

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.4773(9)
_cell_length_b                   13.6425(13)
_cell_length_c                   17.4442(17)
_cell_angle_alpha                69.381(3)
_cell_angle_beta                 75.821(3)
_cell_angle_gamma                87.618(3)
_cell_volume                     2044.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      5.149
_cell_measurement_theta_max      54.438

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36399
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7992
_reflns_number_gt                5729
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.6624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7992
_refine_ls_number_parameters     515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_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 0.01276(10) 0.61544(9) 0.20674(9) 0.1429(4) Uani 1 1 d . . . . .
Cl2 Cl 0.10837(16) 0.51141(10) 0.08742(9) 0.1662(5) Uani 1 1 d . . . . .
C53 C 0.1124(5) 0.5202(3) 0.1838(3) 0.1454(15) Uani 1 1 d . . . . .
H53A H 0.0771 0.4536 0.2282 0.174 Uiso 1 1 calc R U . . .
H53B H 0.2127 0.5325 0.1834 0.174 Uiso 1 1 calc R U . . .
N1 N 0.48046(18) 1.00352(13) 0.22547(10) 0.0571(4) Uani 1 1 d . . . . .
N2 N 0.53697(17) 0.81817(12) 0.20355(10) 0.0537(4) Uani 1 1 d . . . . .
C1 C 0.3941(2) 0.85917(15) 0.09444(12) 0.0527(5) Uani 1 1 d . . . . .
C2 C 0.4338(2) 0.76677(17) 0.07831(14) 0.0626(5) Uani 1 1 d . . . . .
H2 H 0.4977 0.7231 0.1059 0.075 Uiso 1 1 calc R U . . .
C3 C 0.3787(3) 0.74058(19) 0.02210(15) 0.0735(6) Uani 1 1 d . . . . .
H3 H 0.4060 0.6795 0.0113 0.088 Uiso 1 1 calc R U . . .
C4 C 0.2824(3) 0.8047(2) -0.01879(16) 0.0788(7) Uani 1 1 d . . . . .
H4 H 0.2431 0.7854 -0.0556 0.095 Uiso 1 1 calc R U . . .
C5 C 0.2450(3) 0.8958(2) -0.00539(13) 0.0684(6) Uani 1 1 d . . . . .
H5 H 0.1814 0.9384 -0.0341 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3001(2) 0.92711(16) 0.05081(12) 0.0552(5) Uani 1 1 d . . . . .
C7 C 0.2679(2) 1.02650(16) 0.06362(12) 0.0554(5) Uani 1 1 d . . . . .
C8 C 0.1794(2) 1.09969(19) 0.02006(14) 0.0694(6) Uani 1 1 d . . . . .
H8 H 0.1367 1.0835 -0.0169 0.083 Uiso 1 1 calc R U . . .
C9 C 0.1550(3) 1.1940(2) 0.03104(16) 0.0793(7) Uani 1 1 d . . . . .
H9 H 0.0964 1.2412 0.0015 0.095 Uiso 1 1 calc R U . . .
C10 C 0.2172(3) 1.2195(2) 0.08585(16) 0.0785(7) Uani 1 1 d . . . . .
H10 H 0.2008 1.2840 0.0927 0.094 Uiso 1 1 calc R U . . .
C11 C 0.3027(2) 1.15060(17) 0.12998(14) 0.0674(6) Uani 1 1 d . . . . .
H11 H 0.3438 1.1684 0.1669 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3292(2) 1.05312(16) 0.12015(12) 0.0549(5) Uani 1 1 d . . . . .
C13 C 0.4166(2) 0.97864(15) 0.16749(12) 0.0519(5) Uani 1 1 d . . . . .
C14 C 0.4452(2) 0.88610(15) 0.15597(11) 0.0512(5) Uani 1 1 d . . . . .
C15 C 0.6272(2) 0.96935(16) 0.22103(12) 0.0556(5) Uani 1 1 d . . . . .
C16 C 0.7405(3) 1.02983(18) 0.22192(14) 0.0676(6) Uani 1 1 d . . . . .
H16 H 0.7226 1.0937 0.2296 0.081 Uiso 1 1 calc R U . . .
C17 C 0.8809(3) 0.9944(2) 0.21124(15) 0.0730(7) Uani 1 1 d . . . . .
H17 H 0.9566 1.0341 0.2130 0.088 Uiso 1 1 calc R U . . .
C18 C 0.9091(2) 0.9016(2) 0.19808(14) 0.0700(6) Uani 1 1 d . . . . .
H18 H 1.0036 0.8789 0.1907 0.084 Uiso 1 1 calc R U . . .
C19 C 0.7971(2) 0.84168(17) 0.19576(13) 0.0616(5) Uani 1 1 d . . . . .
H19 H 0.8166 0.7794 0.1855 0.074 Uiso 1 1 calc R U . . .
C20 C 0.6561(2) 0.87470(15) 0.20876(12) 0.0535(5) Uani 1 1 d . . . . .
C21 C 0.3874(2) 0.99340(15) 0.30632(13) 0.0574(5) Uani 1 1 d . . . . .
C22 C 0.2445(3) 0.9556(2) 0.32891(15) 0.0765(7) Uani 1 1 d . . . . .
H22 H 0.2086 0.9357 0.2912 0.092 Uiso 1 1 calc R U . . .
C23 C 0.1541(3) 0.9469(2) 0.40641(17) 0.0910(8) Uani 1 1 d . . . . .
H23 H 0.0580 0.9220 0.4198 0.109 Uiso 1 1 calc R U . . .
C24 C 0.2026(3) 0.9740(2) 0.46292(17) 0.0921(8) Uani 1 1 d . . . . .
H24 H 0.1412 0.9675 0.5152 0.111 Uiso 1 1 calc R U . . .
C25 C 0.3421(4) 1.0107(3) 0.44234(18) 0.0978(9) Uani 1 1 d . . . . .
H25 H 0.3765 1.0290 0.4813 0.117 Uiso 1 1 calc R U . . .
C26 C 0.4366(3) 1.0219(2) 0.36368(16) 0.0826(7) Uani 1 1 d . . . . .
H26 H 0.5319 1.0483 0.3505 0.099 Uiso 1 1 calc R U . . .
C27 C 0.4767(2) 0.72400(14) 0.27024(12) 0.0492(4) Uani 1 1 d . . . . .
C28 C 0.5576(2) 0.66553(15) 0.32592(12) 0.0536(5) Uani 1 1 d . . . . .
H28 H 0.6492 0.6913 0.3224 0.064 Uiso 1 1 calc R U . . .
C29 C 0.5033(2) 0.56995(15) 0.38611(12) 0.0527(5) Uani 1 1 d . . . . .
H29 H 0.5600 0.5319 0.4221 0.063 Uiso 1 1 calc R U . . .
C30 C 0.36630(19) 0.52856(14) 0.39466(12) 0.0484(4) Uani 1 1 d . . . . .
C31 C 0.2831(2) 0.59019(16) 0.34250(13) 0.0554(5) Uani 1 1 d . . . . .
H31 H 0.1891 0.5664 0.3486 0.066 Uiso 1 1 calc R U . . .
C32 C 0.3360(2) 0.68625(16) 0.28147(13) 0.0570(5) Uani 1 1 d . . . . .
H32 H 0.2771 0.7260 0.2476 0.068 Uiso 1 1 calc R U . . .
C33 C 0.31221(19) 0.42255(14) 0.45639(11) 0.0476(4) Uani 1 1 d . . . . .
C34 C 0.1773(2) 0.40933(17) 0.51398(12) 0.0572(5) Uani 1 1 d . . . . .
H34 H 0.1209 0.4671 0.5121 0.069 Uiso 1 1 calc R U . . .
C35 C 0.1254(2) 0.31256(19) 0.57380(13) 0.0641(6) Uani 1 1 d . . . . .
H35 H 0.0343 0.3055 0.6111 0.077 Uiso 1 1 calc R U . . .
C36 C 0.2079(2) 0.22739(18) 0.57803(13) 0.0657(6) Uani 1 1 d . . . . .
H36 H 0.1736 0.1621 0.6184 0.079 Uiso 1 1 calc R U . . .
C37 C 0.3423(2) 0.23843(16) 0.52242(13) 0.0596(5) Uani 1 1 d . . . . .
H37 H 0.3984 0.1801 0.5263 0.072 Uiso 1 1 calc R U . . .
C38 C 0.39670(19) 0.33477(15) 0.46029(12) 0.0492(4) Uani 1 1 d . . . . .
C39 C 0.5412(2) 0.33959(15) 0.40026(12) 0.0514(5) Uani 1 1 d . . . . .
C40 C 0.6559(2) 0.30272(17) 0.43212(14) 0.0595(5) Uani 1 1 d . . . . .
H40 H 0.6406 0.2867 0.4900 0.071 Uiso 1 1 calc R U . . .
C41 C 0.8026(2) 0.28400(16) 0.38836(14) 0.0583(5) Uani 1 1 d . . . . .
C42 C 0.9209(2) 0.2949(2) 0.41838(15) 0.0690(6) Uani 1 1 d . . . . .
H42 H 0.9077 0.3199 0.4627 0.083 Uiso 1 1 calc R U . . .
C43 C 1.0581(3) 0.2694(2) 0.38394(17) 0.0810(7) Uani 1 1 d . . . . .
H43 H 1.1364 0.2778 0.4048 0.097 Uiso 1 1 calc R U . . .
C44 C 1.0789(2) 0.2319(2) 0.31904(18) 0.0802(7) Uani 1 1 d . . . . .
H44 H 1.1710 0.2133 0.2964 0.096 Uiso 1 1 calc R U . . .
C45 C 0.9638(3) 0.2218(2) 0.28764(19) 0.0835(8) Uani 1 1 d . . . . .
H45 H 0.9782 0.1973 0.2429 0.100 Uiso 1 1 calc R U . . .
C46 C 0.8265(2) 0.2476(2) 0.32173(17) 0.0759(7) Uani 1 1 d . . . . .
H46 H 0.7491 0.2404 0.2997 0.091 Uiso 1 1 calc R U . . .
C47 C 0.5486(2) 0.38065(16) 0.30799(13) 0.0548(5) Uani 1 1 d . . . . .
C48 C 0.6514(2) 0.45820(19) 0.25092(14) 0.0712(6) Uani 1 1 d . . . . .
H48 H 0.7169 0.4862 0.2706 0.085 Uiso 1 1 calc R U . . .
C49 C 0.6581(3) 0.4944(2) 0.16577(17) 0.0927(8) Uani 1 1 d . . . . .
H49 H 0.7279 0.5463 0.1286 0.111 Uiso 1 1 calc R U . . .
C50 C 0.5628(4) 0.4545(3) 0.13531(18) 0.1003(9) Uani 1 1 d . . . . .
H50 H 0.5676 0.4788 0.0777 0.120 Uiso 1 1 calc R U . . .
C51 C 0.4603(3) 0.3783(3) 0.19068(18) 0.0926(8) Uani 1 1 d . . . . .
H51 H 0.3952 0.3507 0.1705 0.111 Uiso 1 1 calc R U . . .
C52 C 0.4527(2) 0.3420(2) 0.27628(15) 0.0712(6) Uani 1 1 d . . . . .
H52 H 0.3818 0.2907 0.3131 0.085 Uiso 1 1 calc R U . . .


_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 C53 1.679(4) . ?
Cl2 C53 1.737(5) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
N1 C21 1.432(3) . ?
N1 C13 1.437(2) . ?
N1 C15 1.441(3) . ?
N2 C27 1.419(2) . ?
N2 C20 1.431(2) . ?
N2 C14 1.432(2) . ?
C1 C2 1.403(3) . ?
C1 C6 1.414(3) . ?
C1 C14 1.438(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.459(3) . ?
C7 C8 1.409(3) . ?
C7 C12 1.411(3) . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.440(3) . ?
C13 C14 1.353(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.387(3) . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9300 . ?
C21 C26 1.374(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.346(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.350(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.404(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.392(3) . ?
C27 C32 1.393(3) . ?
C28 C29 1.376(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.391(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.383(3) . ?
C30 C33 1.486(3) . ?
C31 C32 1.383(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.392(3) . ?
C33 C38 1.403(3) . ?
C34 C35 1.381(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.364(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.376(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.396(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.494(3) . ?
C39 C40 1.341(3) . ?
C39 C47 1.491(3) . ?
C40 C41 1.473(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.382(3) . ?
C41 C46 1.385(3) . ?
C42 C43 1.377(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.369(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.366(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.379(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C52 1.379(3) . ?
C47 C48 1.389(3) . ?
C48 C49 1.376(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.369(4) . ?
C49 H49 0.9300 . ?
C50 C51 1.369(4) . ?
C50 H50 0.9300 . ?
C51 C52 1.382(4) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?

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
Cl1 C53 Cl2 114.1(2) . . ?
Cl1 C53 H53A 108.7 . . ?
Cl2 C53 H53A 108.7 . . ?
Cl1 C53 H53B 108.7 . . ?
Cl2 C53 H53B 108.7 . . ?
H53A C53 H53B 107.6 . . ?
C21 N1 C13 117.19(16) . . ?
C21 N1 C15 118.77(16) . . ?
C13 N1 C15 111.88(16) . . ?
C27 N2 C20 120.30(15) . . ?
C27 N2 C14 119.86(15) . . ?
C20 N2 C14 112.13(15) . . ?
C2 C1 C6 119.95(19) . . ?
C2 C1 C14 121.38(19) . . ?
C6 C1 C14 118.66(18) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.5(2) . . ?
C5 C6 C7 123.1(2) . . ?
C1 C6 C7 119.45(18) . . ?
C8 C7 C12 117.7(2) . . ?
C8 C7 C6 122.6(2) . . ?
C12 C7 C6 119.75(18) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.7(2) . . ?
C11 C12 C13 121.3(2) . . ?
C7 C12 C13 118.96(18) . . ?
C14 C13 N1 118.65(18) . . ?
C14 C13 C12 121.06(18) . . ?
N1 C13 C12 120.24(18) . . ?
C13 C14 N2 117.40(17) . . ?
C13 C14 C1 121.80(18) . . ?
N2 C14 C1 120.67(17) . . ?
C16 C15 C20 119.5(2) . . ?
C16 C15 N1 123.20(19) . . ?
C20 C15 N1 117.10(17) . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C15 120.36(19) . . ?
C19 C20 N2 122.14(19) . . ?
C15 C20 N2 117.32(17) . . ?
C26 C21 C22 117.8(2) . . ?
C26 C21 N1 121.2(2) . . ?
C22 C21 N1 121.04(19) . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 118.8(3) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C21 C26 C25 119.5(3) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C32 117.86(17) . . ?
C28 C27 N2 120.80(16) . . ?
C32 C27 N2 121.33(17) . . ?
C29 C28 C27 120.59(17) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 121.97(18) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C31 C30 C29 116.95(17) . . ?
C31 C30 C33 121.49(16) . . ?
C29 C30 C33 121.56(16) . . ?
C30 C31 C32 121.85(17) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C27 120.56(18) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C34 C33 C38 118.55(17) . . ?
C34 C33 C30 120.02(17) . . ?
C38 C33 C30 121.39(16) . . ?
C35 C34 C33 121.7(2) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C36 C35 C34 119.80(19) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 119.76(19) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C38 121.8(2) . . ?
C36 C37 H37 119.1 . . ?
C38 C37 H37 119.1 . . ?
C37 C38 C33 118.43(17) . . ?
C37 C38 C39 118.60(18) . . ?
C33 C38 C39 122.97(16) . . ?
C40 C39 C47 123.41(18) . . ?
C40 C39 C38 118.42(18) . . ?
C47 C39 C38 118.11(16) . . ?
C39 C40 C41 129.1(2) . . ?
C39 C40 H40 115.4 . . ?
C41 C40 H40 115.4 . . ?
C42 C41 C46 117.8(2) . . ?
C42 C41 C40 119.4(2) . . ?
C46 C41 C40 122.59(19) . . ?
C43 C42 C41 121.3(2) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C44 C43 C42 119.9(2) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C45 C44 C43 119.7(2) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.5(2) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 120.7(2) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?
C52 C47 C48 117.6(2) . . ?
C52 C47 C39 120.61(18) . . ?
C48 C47 C39 121.83(19) . . ?
C49 C48 C47 121.1(2) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C50 C49 C48 120.5(3) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C49 C50 C51 119.1(3) . . ?
C49 C50 H50 120.4 . . ?
C51 C50 H50 120.4 . . ?
C50 C51 C52 120.6(3) . . ?
C50 C51 H51 119.7 . . ?
C52 C51 H51 119.7 . . ?
C47 C52 C51 121.0(2) . . ?
C47 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?

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 -1.8(3) . . . . ?
C14 C1 C2 C3 177.14(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 177.0(2) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C14 C1 C6 C5 -176.34(17) . . . . ?
C2 C1 C6 C7 -175.66(17) . . . . ?
C14 C1 C6 C7 5.4(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C1 C6 C7 C8 177.70(17) . . . . ?
C5 C6 C7 C12 -179.00(18) . . . . ?
C1 C6 C7 C12 -0.9(3) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 -177.68(19) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C13 -178.7(2) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
C6 C7 C12 C11 177.54(17) . . . . ?
C8 C7 C12 C13 178.15(17) . . . . ?
C6 C7 C12 C13 -3.2(3) . . . . ?
C21 N1 C13 C14 -103.7(2) . . . . ?
C15 N1 C13 C14 38.4(2) . . . . ?
C21 N1 C13 C12 78.9(2) . . . . ?
C15 N1 C13 C12 -138.95(17) . . . . ?
C11 C12 C13 C14 -178.09(18) . . . . ?
C7 C12 C13 C14 2.7(3) . . . . ?
C11 C12 C13 N1 -0.8(3) . . . . ?
C7 C12 C13 N1 179.96(16) . . . . ?
N1 C13 C14 N2 0.6(3) . . . . ?
C12 C13 C14 N2 177.93(16) . . . . ?
N1 C13 C14 C1 -175.27(16) . . . . ?
C12 C13 C14 C1 2.0(3) . . . . ?
C27 N2 C14 C13 109.3(2) . . . . ?
C20 N2 C14 C13 -40.2(2) . . . . ?
C27 N2 C14 C1 -74.8(2) . . . . ?
C20 N2 C14 C1 135.75(18) . . . . ?
C2 C1 C14 C13 174.96(18) . . . . ?
C6 C1 C14 C13 -6.1(3) . . . . ?
C2 C1 C14 N2 -0.8(3) . . . . ?
C6 C1 C14 N2 178.11(16) . . . . ?
C21 N1 C15 C16 -81.1(2) . . . . ?
C13 N1 C15 C16 137.4(2) . . . . ?
C21 N1 C15 C20 103.9(2) . . . . ?
C13 N1 C15 C20 -37.5(2) . . . . ?
C20 C15 C16 C17 -0.5(3) . . . . ?
N1 C15 C16 C17 -175.34(19) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C19 C20 C15 2.4(3) . . . . ?
C18 C19 C20 N2 177.31(18) . . . . ?
C16 C15 C20 C19 -1.3(3) . . . . ?
N1 C15 C20 C19 173.79(18) . . . . ?
C16 C15 C20 N2 -176.52(18) . . . . ?
N1 C15 C20 N2 -1.4(3) . . . . ?
C27 N2 C20 C19 76.0(2) . . . . ?
C14 N2 C20 C19 -134.72(19) . . . . ?
C27 N2 C20 C15 -108.9(2) . . . . ?
C14 N2 C20 C15 40.4(2) . . . . ?
C13 N1 C21 C26 -175.8(2) . . . . ?
C15 N1 C21 C26 44.7(3) . . . . ?
C13 N1 C21 C22 3.5(3) . . . . ?
C15 N1 C21 C22 -135.9(2) . . . . ?
C26 C21 C22 C23 0.1(4) . . . . ?
N1 C21 C22 C23 -179.2(2) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C23 C24 C25 C26 0.4(5) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
N1 C21 C26 C25 -179.9(2) . . . . ?
C24 C25 C26 C21 -1.0(5) . . . . ?
C20 N2 C27 C28 -22.5(3) . . . . ?
C14 N2 C27 C28 -169.50(18) . . . . ?
C20 N2 C27 C32 158.42(19) . . . . ?
C14 N2 C27 C32 11.5(3) . . . . ?
C32 C27 C28 C29 4.5(3) . . . . ?
N2 C27 C28 C29 -174.57(18) . . . . ?
C27 C28 C29 C30 -0.8(3) . . . . ?
C28 C29 C30 C31 -3.1(3) . . . . ?
C28 C29 C30 C33 176.30(18) . . . . ?
C29 C30 C31 C32 3.3(3) . . . . ?
C33 C30 C31 C32 -176.09(19) . . . . ?
C30 C31 C32 C27 0.4(3) . . . . ?
C28 C27 C32 C31 -4.3(3) . . . . ?
N2 C27 C32 C31 174.78(18) . . . . ?
C31 C30 C33 C34 -53.2(3) . . . . ?
C29 C30 C33 C34 127.5(2) . . . . ?
C31 C30 C33 C38 129.2(2) . . . . ?
C29 C30 C33 C38 -50.2(3) . . . . ?
C38 C33 C34 C35 -0.4(3) . . . . ?
C30 C33 C34 C35 -178.14(18) . . . . ?
C33 C34 C35 C36 0.9(3) . . . . ?
C34 C35 C36 C37 -0.2(3) . . . . ?
C35 C36 C37 C38 -0.9(3) . . . . ?
C36 C37 C38 C33 1.4(3) . . . . ?
C36 C37 C38 C39 -177.78(19) . . . . ?
C34 C33 C38 C37 -0.7(3) . . . . ?
C30 C33 C38 C37 176.97(17) . . . . ?
C34 C33 C38 C39 178.43(17) . . . . ?
C30 C33 C38 C39 -3.9(3) . . . . ?
C37 C38 C39 C40 -54.0(3) . . . . ?
C33 C38 C39 C40 126.9(2) . . . . ?
C37 C38 C39 C47 123.2(2) . . . . ?
C33 C38 C39 C47 -55.9(3) . . . . ?
C47 C39 C40 C41 -7.0(3) . . . . ?
C38 C39 C40 C41 170.1(2) . . . . ?
C39 C40 C41 C42 149.0(2) . . . . ?
C39 C40 C41 C46 -36.3(4) . . . . ?
C46 C41 C42 C43 -0.6(4) . . . . ?
C40 C41 C42 C43 174.3(2) . . . . ?
C41 C42 C43 C44 -0.4(4) . . . . ?
C42 C43 C44 C45 1.3(4) . . . . ?
C43 C44 C45 C46 -1.0(4) . . . . ?
C44 C45 C46 C41 -0.1(4) . . . . ?
C42 C41 C46 C45 0.9(4) . . . . ?
C40 C41 C46 C45 -173.9(2) . . . . ?
C40 C39 C47 C52 126.6(2) . . . . ?
C38 C39 C47 C52 -50.4(3) . . . . ?
C40 C39 C47 C48 -53.1(3) . . . . ?
C38 C39 C47 C48 129.9(2) . . . . ?
C52 C47 C48 C49 -0.6(4) . . . . ?
C39 C47 C48 C49 179.2(2) . . . . ?
C47 C48 C49 C50 0.0(4) . . . . ?
C48 C49 C50 C51 0.2(5) . . . . ?
C49 C50 C51 C52 0.1(5) . . . . ?
C48 C47 C52 C51 0.9(4) . . . . ?
C39 C47 C52 C51 -178.9(2) . . . . ?
C50 C51 C52 C47 -0.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19 Cl1 0.93 2.83 3.604(2) 141.5 1_655

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

