# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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#######################################################################

data_mj21120_0m
_database_code_depnum_ccdc_archive 'CCDC 2095611'
loop_
_audit_author_name
_audit_author_address
'Zhicong Tang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(S)-6-(2-benzhydryl-5-chloro-1H-indol-3-yl)-2-chloro-6-phenyl-5,6-dihydroindeno[2,1-b]indole
_chemical_formula_moiety         'C H2 Cl2, C42 H28 Cl2 N2'
_chemical_formula_sum            'C43 H30 Cl4 N2'
_chemical_formula_weight         716.49
_chemical_melting_point          445-458
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.9191(4)
_cell_length_b                   12.8360(4)
_cell_length_c                   20.3504(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.3160(10)
_cell_angle_gamma                90
_cell_volume                     3489.49(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      4.16
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    2.186
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1327 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.7184. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30275
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.966
_diffrn_reflns_theta_min         2.996
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5690
_reflns_number_total             6596
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+2.4121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
 C40(H40), C41(H41), C42(H42), C43(H43)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.60431(6) 0.51667(11) 0.17532(4) 0.0995(4) Uani 1 1 d . . . . .
Cl2 Cl 0.40473(7) 0.51606(9) 0.08416(5) 0.1081(4) Uani 1 1 d . . . . .
C1 C 0.5288(3) 0.4865(3) 0.09563(19) 0.0876(11) Uani 1 1 d . . . . .
H1A H 0.534800 0.411082 0.087471 0.105 Uiso 1 1 calc R . . . .
H1B H 0.552846 0.524683 0.061028 0.105 Uiso 1 1 calc R . . . .
Cl3 Cl 0.48440(4) 0.16797(5) 0.76727(3) 0.05031(18) Uani 1 1 d . . . . .
Cl4 Cl 0.33360(5) 0.07268(5) 0.27957(4) 0.0708(3) Uani 1 1 d . . . . .
N1 N 0.66097(12) 0.35433(13) 0.56637(8) 0.0289(4) Uani 1 1 d . . . . .
H1 H 0.678834 0.418012 0.558894 0.035 Uiso 1 1 calc R . . . .
N2 N 0.59228(12) 0.43666(14) 0.32995(8) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.589340 0.497277 0.309279 0.039 Uiso 1 1 calc R . . . .
C2 C 0.53774(15) 0.22725(19) 0.70868(10) 0.0359(5) Uani 1 1 d . . . . .
C3 C 0.55742(15) 0.16639(18) 0.65818(10) 0.0343(5) Uani 1 1 d . . . . .
H3 H 0.542189 0.094095 0.654906 0.041 Uiso 1 1 calc R . . . .
C4 C 0.60069(14) 0.21510(16) 0.61187(9) 0.0296(4) Uani 1 1 d . . . . .
C5 C 0.61999(13) 0.32368(16) 0.61810(9) 0.0282(4) Uani 1 1 d . . . . .
C6 C 0.66857(14) 0.26761(15) 0.52913(9) 0.0273(4) Uani 1 1 d . . . . .
C7 C 0.63367(14) 0.18163(16) 0.55438(10) 0.0281(4) Uani 1 1 d . . . . .
C8 C 0.64703(14) 0.09086(16) 0.51441(10) 0.0297(4) Uani 1 1 d . . . . .
C9 C 0.68771(13) 0.12695(15) 0.46250(9) 0.0268(4) Uani 1 1 d . . . . .
C10 C 0.70700(13) 0.24616(15) 0.46789(9) 0.0261(4) Uani 1 1 d . . . . .
C11 C 0.64729(13) 0.30749(15) 0.40509(9) 0.0253(4) Uani 1 1 d . . . . .
C12 C 0.66693(14) 0.40668(16) 0.38687(9) 0.0277(4) Uani 1 1 d . . . . .
C13 C 0.52325(14) 0.35855(16) 0.31015(10) 0.0301(4) Uani 1 1 d . . . . .
C14 C 0.55414(13) 0.27526(16) 0.35661(9) 0.0268(4) Uani 1 1 d . . . . .
C15 C 0.49424(14) 0.18550(17) 0.34707(10) 0.0328(4) Uani 1 1 d . . . . .
H15 H 0.511692 0.127917 0.377414 0.039 Uiso 1 1 calc R . . . .
C16 C 0.40911(15) 0.18345(18) 0.29218(11) 0.0389(5) Uani 1 1 d . . . . .
C17 C 0.37974(16) 0.26647(19) 0.24625(11) 0.0393(5) Uani 1 1 d . . . . .
H17 H 0.320488 0.261382 0.209250 0.047 Uiso 1 1 calc R . . . .
C18 C 0.43692(15) 0.35517(18) 0.25493(10) 0.0362(5) Uani 1 1 d . . . . .
H18 H 0.418409 0.412405 0.224380 0.043 Uiso 1 1 calc R . . . .
C19 C 0.74756(14) 0.48482(15) 0.42001(9) 0.0285(4) Uani 1 1 d . . . . .
H19 H 0.809719 0.443827 0.440964 0.034 Uiso 1 1 calc R . . . .
C20 C 0.77139(14) 0.55672(16) 0.36643(10) 0.0307(4) Uani 1 1 d . . . . .
C21 C 0.73463(16) 0.65671(17) 0.35367(11) 0.0367(5) Uani 1 1 d . . . . .
H21 H 0.692225 0.684005 0.378814 0.044 Uiso 1 1 calc R . . . .
C22 C 0.75915(17) 0.71810(19) 0.30422(11) 0.0410(5) Uani 1 1 d . . . . .
H22 H 0.733663 0.787001 0.296084 0.049 Uiso 1 1 calc R . . . .
C23 C 0.82000(17) 0.6796(2) 0.26712(11) 0.0425(5) Uani 1 1 d . . . . .
H23 H 0.837143 0.721851 0.233795 0.051 Uiso 1 1 calc R . . . .
C24 C 0.85575(19) 0.5797(2) 0.27857(12) 0.0466(6) Uani 1 1 d . . . . .
H24 H 0.896822 0.552224 0.252516 0.056 Uiso 1 1 calc R . . . .
C25 C 0.83210(18) 0.51874(19) 0.32805(12) 0.0419(5) Uani 1 1 d . . . . .
H25 H 0.857799 0.449885 0.335868 0.050 Uiso 1 1 calc R . . . .
C26 C 0.72239(14) 0.54283(16) 0.47839(10) 0.0297(4) Uani 1 1 d . . . . .
C27 C 0.79711(16) 0.56068(18) 0.53902(11) 0.0387(5) Uani 1 1 d . . . . .
H27 H 0.863630 0.538437 0.543113 0.046 Uiso 1 1 calc R . . . .
C28 C 0.77528(19) 0.6108(2) 0.59368(12) 0.0501(6) Uani 1 1 d . . . . .
H28 H 0.826706 0.621985 0.635027 0.060 Uiso 1 1 calc R . . . .
C29 C 0.67908(19) 0.6443(2) 0.58803(12) 0.0488(6) Uani 1 1 d . . . . .
H29 H 0.664421 0.678750 0.625406 0.059 Uiso 1 1 calc R . . . .
C30 C 0.60434(18) 0.62796(19) 0.52822(12) 0.0436(5) Uani 1 1 d . . . . .
H30 H 0.538262 0.651605 0.524189 0.052 Uiso 1 1 calc R . . . .
C31 C 0.62560(16) 0.57684(17) 0.47378(11) 0.0357(5) Uani 1 1 d . . . . .
H31 H 0.573519 0.564913 0.432891 0.043 Uiso 1 1 calc R . . . .
C32 C 0.82070(13) 0.26164(15) 0.48343(10) 0.0272(4) Uani 1 1 d . . . . .
C33 C 0.86701(14) 0.25296(16) 0.43136(10) 0.0321(4) Uani 1 1 d . . . . .
H33 H 0.827331 0.241541 0.385674 0.039 Uiso 1 1 calc R . . . .
C34 C 0.97004(16) 0.26069(18) 0.44500(12) 0.0402(5) Uani 1 1 d . . . . .
H34 H 1.000413 0.254413 0.408817 0.048 Uiso 1 1 calc R . . . .
C35 C 1.02864(16) 0.2775(2) 0.51119(13) 0.0479(6) Uani 1 1 d . . . . .
H35 H 1.099321 0.282437 0.520679 0.058 Uiso 1 1 calc R . . . .
C36 C 0.98423(16) 0.2871(2) 0.56312(12) 0.0473(6) Uani 1 1 d . . . . .
H36 H 1.024339 0.299375 0.608585 0.057 Uiso 1 1 calc R . . . .
C37 C 0.88038(15) 0.27883(18) 0.54961(11) 0.0368(5) Uani 1 1 d . . . . .
H37 H 0.850441 0.285039 0.586023 0.044 Uiso 1 1 calc R . . . .
C38 C 0.70881(14) 0.05807(16) 0.41634(10) 0.0320(4) Uani 1 1 d . . . . .
H38 H 0.736026 0.082299 0.381236 0.038 Uiso 1 1 calc R . . . .
C39 C 0.68953(17) -0.04768(18) 0.42208(11) 0.0399(5) Uani 1 1 d . . . . .
H39 H 0.702970 -0.095767 0.390283 0.048 Uiso 1 1 calc R . . . .
C40 C 0.65106(18) -0.08307(18) 0.47361(12) 0.0440(5) Uani 1 1 d . . . . .
H40 H 0.639336 -0.155461 0.477279 0.053 Uiso 1 1 calc R . . . .
C41 C 0.62928(16) -0.01429(17) 0.52013(12) 0.0389(5) Uani 1 1 d . . . . .
H41 H 0.602590 -0.039098 0.555349 0.047 Uiso 1 1 calc R . . . .
C42 C 0.59971(15) 0.38366(18) 0.66958(10) 0.0338(4) Uani 1 1 d . . . . .
H42 H 0.613554 0.456245 0.673067 0.041 Uiso 1 1 calc R . . . .
C43 C 0.55869(15) 0.33365(19) 0.71542(10) 0.0372(5) Uani 1 1 d . . . . .
H43 H 0.544698 0.371820 0.751663 0.045 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 1.711(4) . ?
Cl2 C1 1.719(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
Cl3 C2 1.746(2) . ?
Cl4 C16 1.744(2) . ?
N1 H1 0.8800 . ?
N1 C5 1.388(2) . ?
N1 C6 1.367(3) . ?
N2 H2 0.8800 . ?
N2 C12 1.376(2) . ?
N2 C13 1.369(3) . ?
C2 C3 1.378(3) . ?
C2 C43 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(3) . ?
C4 C5 1.418(3) . ?
C4 C7 1.437(3) . ?
C5 C42 1.392(3) . ?
C6 C7 1.363(3) . ?
C6 C10 1.513(3) . ?
C7 C8 1.462(3) . ?
C8 C9 1.410(3) . ?
C8 C41 1.383(3) . ?
C9 C10 1.552(3) . ?
C9 C38 1.380(3) . ?
C10 C11 1.532(3) . ?
C10 C32 1.537(3) . ?
C11 C12 1.375(3) . ?
C11 C14 1.451(3) . ?
C12 C19 1.515(3) . ?
C13 C14 1.412(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.403(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 C17 1.401(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9500 . ?
C19 H19 1.0000 . ?
C19 C20 1.534(3) . ?
C19 C26 1.524(3) . ?
C20 C21 1.379(3) . ?
C20 C25 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.375(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 C31 1.394(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.377(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.389(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(3) . ?
C32 C37 1.387(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.386(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.382(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.371(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.397(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.395(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.382(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.389(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.381(3) . ?
C43 H43 0.9500 . ?

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 C1 Cl2 113.9(2) . . ?
Cl1 C1 H1A 108.8 . . ?
Cl1 C1 H1B 108.8 . . ?
Cl2 C1 H1A 108.8 . . ?
Cl2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C5 N1 H1 126.2 . . ?
C6 N1 H1 126.2 . . ?
C6 N1 C5 107.58(16) . . ?
C12 N2 H2 124.9 . . ?
C13 N2 H2 124.9 . . ?
C13 N2 C12 110.16(16) . . ?
C3 C2 Cl3 118.29(18) . . ?
C3 C2 C43 123.25(19) . . ?
C43 C2 Cl3 118.46(16) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.5(2) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C5 119.03(18) . . ?
C3 C4 C7 135.3(2) . . ?
C5 C4 C7 105.70(17) . . ?
N1 C5 C4 108.59(17) . . ?
N1 C5 C42 128.89(19) . . ?
C42 C5 C4 122.52(18) . . ?
N1 C6 C10 134.83(17) . . ?
C7 C6 N1 111.03(17) . . ?
C7 C6 C10 114.14(17) . . ?
C4 C7 C8 144.14(18) . . ?
C6 C7 C4 107.10(17) . . ?
C6 C7 C8 108.71(17) . . ?
C9 C8 C7 107.20(17) . . ?
C41 C8 C7 132.61(19) . . ?
C41 C8 C9 120.18(19) . . ?
C8 C9 C10 111.65(16) . . ?
C38 C9 C8 120.44(19) . . ?
C38 C9 C10 127.86(17) . . ?
C6 C10 C9 98.24(15) . . ?
C6 C10 C11 111.04(15) . . ?
C6 C10 C32 112.87(15) . . ?
C11 C10 C9 113.90(15) . . ?
C11 C10 C32 113.02(15) . . ?
C32 C10 C9 106.84(15) . . ?
C12 C11 C10 126.76(17) . . ?
C12 C11 C14 106.74(16) . . ?
C14 C11 C10 126.31(17) . . ?
N2 C12 C19 118.65(17) . . ?
C11 C12 N2 109.01(16) . . ?
C11 C12 C19 132.19(17) . . ?
N2 C13 C14 107.52(16) . . ?
N2 C13 C18 129.33(19) . . ?
C18 C13 C14 123.15(19) . . ?
C13 C14 C11 106.57(17) . . ?
C15 C14 C11 135.29(18) . . ?
C15 C14 C13 118.14(17) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 H15 121.0 . . ?
C15 C16 Cl4 118.62(18) . . ?
C15 C16 C17 123.2(2) . . ?
C17 C16 Cl4 118.13(16) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.71(19) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 121.1 . . ?
C17 C18 C13 117.8(2) . . ?
C17 C18 H18 121.1 . . ?
C12 C19 H19 106.6 . . ?
C12 C19 C20 111.27(15) . . ?
C12 C19 C26 111.52(15) . . ?
C20 C19 H19 106.6 . . ?
C26 C19 H19 106.6 . . ?
C26 C19 C20 113.77(16) . . ?
C21 C20 C19 123.42(18) . . ?
C21 C20 C25 118.20(19) . . ?
C25 C20 C19 118.38(19) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.1(2) . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C19 119.58(18) . . ?
C27 C26 C31 118.40(19) . . ?
C31 C26 C19 122.01(17) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0(2) . . ?
C31 C30 H30 120.0 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.8(2) . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C10 120.24(16) . . ?
C37 C32 C10 121.43(17) . . ?
C37 C32 C33 118.24(18) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.11(19) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.1(2) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.7(2) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.5(2) . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 120.5(2) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C9 C38 H38 120.5 . . ?
C9 C38 C39 118.92(19) . . ?
C39 C38 H38 120.5 . . ?
C38 C39 H39 119.7 . . ?
C40 C39 C38 120.5(2) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.5 . . ?
C39 C40 C41 120.9(2) . . ?
C41 C40 H40 119.5 . . ?
C8 C41 C40 119.0(2) . . ?
C8 C41 H41 120.5 . . ?
C40 C41 H41 120.5 . . ?
C5 C42 H42 121.3 . . ?
C43 C42 C5 117.5(2) . . ?
C43 C42 H42 121.3 . . ?
C2 C43 H43 119.9 . . ?
C42 C43 C2 120.2(2) . . ?
C42 C43 H43 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/n-hexane=1:1'
_exptl_crystal_preparation       fluorescence
####################################################################### 
# 
# 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_exp_12297_sq
_database_code_depnum_ccdc_archive 'CCDC 2100661'
loop_
_audit_author_name
_audit_author_address
'Zhicong Tang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2021-07-31 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
6-(2-(bis(4-(trifluoromethyl)phenyl)methyl)-1H-indol-3-yl)-9-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)-5,6-dihydroindeno[2,1-b]indole
_chemical_name_common            ?
_chemical_melting_point          325.4-329
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H26 F12 N2'
_chemical_formula_weight         178.21

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   12.1173(8)
_cell_length_b                   13.9790(9)
_cell_length_c                   17.7969(7)
_cell_angle_alpha                78.960(4)
_cell_angle_beta                 80.192(5)
_cell_angle_gamma                68.596(6)
_cell_volume                     2738.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4768
_cell_measurement_theta_min      4.4740
_cell_measurement_theta_max      69.8710

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.108
_exptl_crystal_F_000             94
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.31020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17778
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.430
_diffrn_reflns_theta_max         67.248
_diffrn_reflns_theta_full        67.248
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9769
_reflns_number_gt                6026
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9769
_refine_ls_number_parameters     653
_refine_ls_number_restraints     700
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.3679
_refine_ls_wR_factor_gt          0.3321
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_restrained_S_all      1.314
_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
F1 F 0.2034(14) 0.1975(14) -0.0232(13) 0.151(6) Uani 0.258(12) 1 d D U P A 1
F2 F 0.279(3) 0.0666(14) 0.0591(9) 0.165(6) Uani 0.258(12) 1 d D U P A 1
F3 F 0.3869(11) 0.1122(17) -0.0373(10) 0.136(5) Uani 0.258(12) 1 d D U P A 1
F4 F 0.1912(18) 0.8601(13) 0.0196(8) 0.207(6) Uani 0.377(10) 1 d D U P B 1
F5 F 0.1630(13) 0.8822(15) 0.1369(9) 0.176(6) Uani 0.377(10) 1 d D U P B 1
F6 F 0.3330(9) 0.8574(8) 0.0743(9) 0.162(4) Uani 0.377(10) 1 d D U P B 1
F7 F 0.3450(6) 0.8904(5) 0.2515(8) 0.176(4) Uani 0.608(11) 1 d D U P C 1
F8 F 0.4872(14) 0.8858(6) 0.3084(6) 0.185(4) Uani 0.608(11) 1 d D U P C 1
F9 F 0.5131(12) 0.8746(6) 0.1886(5) 0.182(4) Uani 0.608(11) 1 d D U P C 1
F10 F 0.8586(9) 0.1929(13) 0.6295(5) 0.172(5) Uani 0.491(12) 1 d D U P D 1
F11 F 1.0001(10) 0.2160(12) 0.5497(8) 0.172(5) Uani 0.491(12) 1 d D U P D 1
F12 F 0.9599(14) 0.0803(6) 0.5576(8) 0.176(5) Uani 0.491(12) 1 d D U P D 1
F1' F 0.1972(6) 0.1252(6) 0.0469(4) 0.142(2) Uani 0.742(12) 1 d D U P A 2
F2' F 0.3736(6) 0.0603(5) 0.0000(6) 0.162(3) Uani 0.742(12) 1 d D U P A 2
F3' F 0.2617(9) 0.2072(6) -0.0515(4) 0.155(3) Uani 0.742(12) 1 d D U P A 2
F4' F 0.1163(7) 0.8480(5) 0.0722(6) 0.169(3) Uani 0.623(10) 1 d D U P B 2
F5' F 0.2219(12) 0.8859(9) 0.1347(7) 0.191(4) Uani 0.623(10) 1 d D U P B 2
F6' F 0.2807(9) 0.8562(7) 0.0179(6) 0.200(5) Uani 0.623(10) 1 d D U P B 2
F7' F 0.3856(17) 0.8957(9) 0.3065(10) 0.186(6) Uani 0.392(11) 1 d D U P C 2
F8' F 0.5640(10) 0.8622(9) 0.2573(13) 0.177(5) Uani 0.392(11) 1 d D U P C 2
F9' F 0.4294(19) 0.8785(11) 0.1880(7) 0.167(5) Uani 0.392(11) 1 d D U P C 2
F10' F 0.8732(12) 0.1157(12) 0.6102(7) 0.180(5) Uani 0.509(12) 1 d D U P D 2
F11' F 0.9254(14) 0.2460(7) 0.6001(8) 0.188(5) Uani 0.509(12) 1 d D U P D 2
F12' F 1.0141(8) 0.1316(13) 0.5270(6) 0.185(5) Uani 0.509(12) 1 d D U P D 2
N1 N 0.3169(3) 0.3336(3) 0.30960(17) 0.0702(8) Uani 1 1 d . U . . .
H1 H 0.266443 0.325893 0.284751 0.084 Uiso 1 1 calc R U . . .
N2 N 0.7340(3) 0.2931(2) 0.21605(17) 0.0683(7) Uani 1 1 d . U . . .
H2A H 0.741898 0.229595 0.234203 0.082 Uiso 1 1 calc R U . . .
C1 C 0.3096(3) 0.3251(3) 0.3884(2) 0.0688(9) Uani 1 1 d . U . . .
C2 C 0.2251(4) 0.3016(3) 0.4442(2) 0.0807(11) Uani 1 1 d . U . . .
H2 H 0.162811 0.286340 0.431215 0.097 Uiso 1 1 calc R U . . .
C3 C 0.2370(4) 0.3017(4) 0.5199(3) 0.0873(12) Uani 1 1 d . U . . .
H3 H 0.179826 0.289133 0.558583 0.105 Uiso 1 1 calc R U . . .
C4 C 0.3328(4) 0.3203(4) 0.5396(2) 0.0842(11) Uani 1 1 d . U . . .
H4 H 0.339665 0.318303 0.591185 0.101 Uiso 1 1 calc R U . . .
C5 C 0.4171(4) 0.3415(3) 0.4843(2) 0.0728(10) Uani 1 1 d . U . . .
H5 H 0.480174 0.354469 0.498524 0.087 Uiso 1 1 calc R U . . .
C6 C 0.4094(3) 0.3439(3) 0.4064(2) 0.0635(8) Uani 1 1 d . U . . .
C7 C 0.4766(3) 0.3617(3) 0.33460(19) 0.0598(8) Uani 1 1 d . U . . .
C8 C 0.4186(3) 0.3566(3) 0.27612(19) 0.0636(8) Uani 1 1 d . U . . .
C9 C 0.4384(3) 0.3839(3) 0.1908(2) 0.0649(8) Uani 1 1 d . U . . .
H9 H 0.524748 0.365112 0.177132 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3832(4) 0.5018(3) 0.1657(2) 0.0737(10) Uani 1 1 d . U . . .
C11 C 0.2971(4) 0.5688(4) 0.2103(3) 0.0863(11) Uani 1 1 d . U . . .
H11 H 0.270189 0.543273 0.259381 0.104 Uiso 1 1 calc R U . . .
C12 C 0.2506(5) 0.6713(4) 0.1840(3) 0.1081(16) Uani 1 1 d . U . . .
H12 H 0.190472 0.715082 0.214407 0.130 Uiso 1 1 calc R U . . .
C13 C 0.2920(6) 0.7110(4) 0.1125(3) 0.1096(16) Uani 1 1 d D U . . .
C14 C 0.3771(8) 0.6500(5) 0.0699(3) 0.140(3) Uani 1 1 d . U . . .
H14 H 0.404704 0.677786 0.021876 0.168 Uiso 1 1 calc R U . . .
C15 C 0.4285(6) 0.5418(4) 0.0953(3) 0.1163(19) Uani 1 1 d . U . . .
H15 H 0.490863 0.499236 0.065358 0.140 Uiso 1 1 calc R U . . .
C16 C 0.3970(3) 0.3219(3) 0.1474(2) 0.0667(9) Uani 1 1 d . U . . .
C17 C 0.4758(4) 0.2258(4) 0.1305(3) 0.0906(13) Uani 1 1 d . U . . .
H17 H 0.551160 0.199352 0.147378 0.109 Uiso 1 1 calc R U . . .
C18 C 0.4415(5) 0.1688(4) 0.0882(3) 0.1037(16) Uani 1 1 d . U . . .
H18 H 0.494294 0.104491 0.076827 0.124 Uiso 1 1 calc R U . . .
C19 C 0.3322(4) 0.2067(3) 0.0638(2) 0.0808(11) Uani 1 1 d D U . . .
C20 C 0.2540(4) 0.2988(3) 0.0807(2) 0.0806(11) Uani 1 1 d . U . . .
H20 H 0.178235 0.323175 0.064664 0.097 Uiso 1 1 calc R U . . .
C21 C 0.2855(4) 0.3578(3) 0.1220(2) 0.0762(10) Uani 1 1 d . U . . .
H21 H 0.231162 0.421924 0.132618 0.091 Uiso 1 1 calc R U . . .
C22 C 0.7885(3) 0.3287(3) 0.1464(2) 0.0699(9) Uani 1 1 d . U . . .
C23 C 0.8662(4) 0.2707(4) 0.0916(3) 0.0872(12) Uani 1 1 d . U . . .
H23 H 0.887255 0.198910 0.097514 0.105 Uiso 1 1 calc R U . . .
C24 C 0.9106(4) 0.3246(5) 0.0281(3) 0.0986(14) Uani 1 1 d . U . . .
H24 H 0.962064 0.288554 -0.010216 0.118 Uiso 1 1 calc R U . . .
C25 C 0.8802(5) 0.4319(5) 0.0200(3) 0.1019(15) Uani 1 1 d . U . . .
H25 H 0.914343 0.465534 -0.022596 0.122 Uiso 1 1 calc R U . . .
C26 C 0.8012(4) 0.4891(4) 0.0731(3) 0.0876(12) Uani 1 1 d . U . . .
H26 H 0.779116 0.560993 0.065948 0.105 Uiso 1 1 calc R U . . .
C27 C 0.7542(3) 0.4365(3) 0.1389(2) 0.0702(9) Uani 1 1 d . U . . .
C28 C 0.6766(3) 0.4657(3) 0.2061(2) 0.0687(9) Uani 1 1 d . U . . .
C29 C 0.6661(3) 0.3781(3) 0.2494(2) 0.0644(8) Uani 1 1 d . U . . .
C30 C 0.5855(3) 0.3959(3) 0.3245(2) 0.0643(8) Uani 1 1 d . U . . .
C31 C 0.5467(3) 0.5159(3) 0.3144(2) 0.0648(8) Uani 1 1 d . U . . .
C32 C 0.4668(4) 0.5795(3) 0.3625(2) 0.0781(10) Uani 1 1 d . U . . .
H32 H 0.430660 0.552498 0.407702 0.094 Uiso 1 1 calc R U . . .
C33 C 0.4401(4) 0.6873(3) 0.3423(3) 0.0859(12) Uani 1 1 d . U . . .
H33 H 0.385104 0.733239 0.373612 0.103 Uiso 1 1 calc R U . . .
C34 C 0.4967(4) 0.7231(3) 0.2755(3) 0.0845(11) Uani 1 1 d D U . . .
C35 C 0.5742(4) 0.6609(3) 0.2250(3) 0.0790(10) Uani 1 1 d . U . . .
H35 H 0.607731 0.688444 0.178982 0.095 Uiso 1 1 calc R U . . .
C36 C 0.6010(3) 0.5542(3) 0.2455(2) 0.0674(9) Uani 1 1 d . U . . .
C37 C 0.6662(3) 0.3424(3) 0.3887(2) 0.0691(9) Uani 1 1 d . U . . .
C38 C 0.6969(4) 0.2354(3) 0.4095(3) 0.0802(11) Uani 1 1 d . U . . .
H38 H 0.664670 0.198792 0.386446 0.096 Uiso 1 1 calc R U . . .
C39 C 0.7763(4) 0.1823(4) 0.4653(3) 0.0971(14) Uani 1 1 d . U . . .
H39 H 0.797249 0.110847 0.479462 0.117 Uiso 1 1 calc R U . . .
C40 C 0.8225(4) 0.2398(5) 0.4986(3) 0.1000(14) Uani 1 1 d D U . . .
C41 C 0.7946(5) 0.3429(5) 0.4794(3) 0.1010(14) Uani 1 1 d . U . . .
H41 H 0.827566 0.379157 0.502389 0.121 Uiso 1 1 calc R U . . .
C42 C 0.7150(4) 0.3949(4) 0.4243(3) 0.0836(11) Uani 1 1 d . U . . .
H42 H 0.694440 0.466400 0.411299 0.100 Uiso 1 1 calc R U . . .
C43 C 0.2961(5) 0.1502(4) 0.0168(3) 0.1099(15) Uani 1 1 d D U . . .
C44 C 0.2360(7) 0.8213(4) 0.0866(4) 0.149(2) Uani 1 1 d D U . . .
C45 C 0.4666(5) 0.8366(4) 0.2567(3) 0.1236(18) Uani 1 1 d D U . . .
C46 C 0.9060(5) 0.1854(5) 0.5566(3) 0.133(2) Uani 1 1 d D 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
F1 C43 1.325(8) . ?
F2 C43 1.327(8) . ?
F3 C43 1.353(8) . ?
F4 C44 1.329(8) . ?
F5 C44 1.334(9) . ?
F6 C44 1.411(8) . ?
F7 C45 1.399(7) . ?
F8 C45 1.351(6) . ?
F9 C45 1.344(7) . ?
F10 C46 1.333(7) . ?
F11 C46 1.336(7) . ?
F12 C46 1.371(7) . ?
F1' C43 1.363(6) . ?
F2' C43 1.318(6) . ?
F3' C43 1.358(6) . ?
F4' C44 1.414(7) . ?
F5' C44 1.308(8) . ?
F6' C44 1.328(7) . ?
F7' C45 1.350(8) . ?
F8' C45 1.354(7) . ?
F9' C45 1.327(8) . ?
F10' C46 1.347(7) . ?
F11' C46 1.352(7) . ?
F12' C46 1.326(7) . ?
N1 C1 1.375(5) . ?
N1 C8 1.393(5) . ?
N2 C29 1.354(5) . ?
N2 C22 1.394(5) . ?
C1 C2 1.384(6) . ?
C1 C6 1.425(5) . ?
C2 C3 1.380(6) . ?
C3 C4 1.389(7) . ?
C4 C5 1.367(6) . ?
C5 C6 1.399(5) . ?
C6 C7 1.425(5) . ?
C7 C8 1.378(5) . ?
C7 C30 1.532(5) . ?
C8 C9 1.493(5) . ?
C9 C16 1.518(5) . ?
C9 C10 1.543(5) . ?
C10 C11 1.373(6) . ?
C10 C15 1.380(6) . ?
C11 C12 1.355(7) . ?
C12 C13 1.377(8) . ?
C13 C14 1.305(9) . ?
C13 C44 1.456(6) . ?
C14 C15 1.424(8) . ?
C16 C21 1.382(5) . ?
C16 C17 1.388(6) . ?
C17 C18 1.397(6) . ?
C18 C19 1.349(6) . ?
C19 C20 1.345(6) . ?
C19 C43 1.464(5) . ?
C20 C21 1.385(5) . ?
C22 C23 1.389(6) . ?
C22 C27 1.395(6) . ?
C23 C24 1.378(7) . ?
C24 C25 1.392(8) . ?
C25 C26 1.368(7) . ?
C26 C27 1.409(6) . ?
C27 C28 1.416(5) . ?
C28 C29 1.352(5) . ?
C28 C36 1.466(5) . ?
C29 C30 1.518(5) . ?
C30 C37 1.530(5) . ?
C30 C31 1.551(5) . ?
C31 C32 1.357(5) . ?
C31 C36 1.398(5) . ?
C32 C33 1.407(6) . ?
C33 C34 1.371(6) . ?
C34 C35 1.365(6) . ?
C34 C45 1.476(5) . ?
C35 C36 1.393(5) . ?
C37 C42 1.382(5) . ?
C37 C38 1.394(6) . ?
C38 C39 1.409(6) . ?
C39 C40 1.391(7) . ?
C40 C41 1.343(8) . ?
C40 C46 1.471(6) . ?
C41 C42 1.400(7) . ?

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 C8 109.7(3) . . ?
C29 N2 C22 106.4(3) . . ?
N1 C1 C2 129.4(4) . . ?
N1 C1 C6 107.7(3) . . ?
C2 C1 C6 122.9(4) . . ?
C3 C2 C1 117.3(4) . . ?
C2 C3 C4 121.3(4) . . ?
C5 C4 C3 121.0(4) . . ?
C4 C5 C6 120.5(4) . . ?
C5 C6 C7 137.0(3) . . ?
C5 C6 C1 116.9(3) . . ?
C7 C6 C1 106.1(3) . . ?
C8 C7 C6 108.7(3) . . ?
C8 C7 C30 125.9(3) . . ?
C6 C7 C30 124.9(3) . . ?
C7 C8 N1 107.8(3) . . ?
C7 C8 C9 131.5(3) . . ?
N1 C8 C9 120.1(3) . . ?
C8 C9 C16 112.6(3) . . ?
C8 C9 C10 111.5(3) . . ?
C16 C9 C10 112.1(3) . . ?
C11 C10 C15 118.8(4) . . ?
C11 C10 C9 124.2(4) . . ?
C15 C10 C9 117.0(4) . . ?
C12 C11 C10 121.1(5) . . ?
C11 C12 C13 120.3(5) . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 C44 122.4(6) . . ?
C12 C13 C44 117.6(6) . . ?
C13 C14 C15 121.6(5) . . ?
C10 C15 C14 118.1(5) . . ?
C21 C16 C17 118.2(4) . . ?
C21 C16 C9 123.1(3) . . ?
C17 C16 C9 118.6(3) . . ?
C16 C17 C18 119.8(4) . . ?
C19 C18 C17 120.3(4) . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 C43 118.1(4) . . ?
C18 C19 C43 121.3(4) . . ?
C19 C20 C21 120.5(4) . . ?
C16 C21 C20 120.4(4) . . ?
C23 C22 N2 128.0(4) . . ?
C23 C22 C27 123.0(4) . . ?
N2 C22 C27 109.0(3) . . ?
C24 C23 C22 116.8(5) . . ?
C23 C24 C25 121.4(5) . . ?
C26 C25 C24 121.6(5) . . ?
C25 C26 C27 118.5(5) . . ?
C22 C27 C26 118.7(4) . . ?
C22 C27 C28 105.8(3) . . ?
C26 C27 C28 135.5(4) . . ?
C29 C28 C27 107.4(4) . . ?
C29 C28 C36 108.3(3) . . ?
C27 C28 C36 144.2(4) . . ?
C28 C29 N2 111.3(3) . . ?
C28 C29 C30 114.2(3) . . ?
N2 C29 C30 134.5(3) . . ?
C29 C30 C37 105.9(3) . . ?
C29 C30 C7 115.9(3) . . ?
C37 C30 C7 112.4(3) . . ?
C29 C30 C31 98.3(3) . . ?
C37 C30 C31 112.8(3) . . ?
C7 C30 C31 110.7(3) . . ?
C32 C31 C36 122.1(4) . . ?
C32 C31 C30 126.5(3) . . ?
C36 C31 C30 111.3(3) . . ?
C31 C32 C33 118.3(4) . . ?
C34 C33 C32 118.6(4) . . ?
C35 C34 C33 124.0(4) . . ?
C35 C34 C45 119.0(4) . . ?
C33 C34 C45 116.9(4) . . ?
C34 C35 C36 117.0(4) . . ?
C35 C36 C31 119.8(4) . . ?
C35 C36 C28 132.3(4) . . ?
C31 C36 C28 107.9(3) . . ?
C42 C37 C38 118.4(4) . . ?
C42 C37 C30 122.8(4) . . ?
C38 C37 C30 118.7(3) . . ?
C37 C38 C39 120.6(4) . . ?
C40 C39 C38 118.0(5) . . ?
C41 C40 C39 122.7(4) . . ?
C41 C40 C46 118.7(5) . . ?
C39 C40 C46 118.7(5) . . ?
C40 C41 C42 118.7(4) . . ?
C37 C42 C41 121.6(5) . . ?
F1 C43 F2 106.9(8) . . ?
F1 C43 F3 103.5(8) . . ?
F2 C43 F3 104.4(8) . . ?
F2' C43 F3' 105.9(6) . . ?
F2' C43 F1' 102.2(5) . . ?
F3' C43 F1' 101.0(5) . . ?
F2' C43 C19 117.7(5) . . ?
F1 C43 C19 121.0(9) . . ?
F2 C43 C19 110.3(8) . . ?
F3 C43 C19 109.3(7) . . ?
F3' C43 C19 112.7(5) . . ?
F1' C43 C19 115.5(5) . . ?
F5' C44 F6' 109.0(7) . . ?
F4 C44 F5 105.5(8) . . ?
F4 C44 F6 100.0(7) . . ?
F5 C44 F6 100.4(7) . . ?
F5' C44 F4' 100.0(7) . . ?
F6' C44 F4' 99.4(6) . . ?
F5' C44 C13 117.6(8) . . ?
F6' C44 C13 115.3(6) . . ?
F4 C44 C13 124.5(9) . . ?
F5 C44 C13 119.2(11) . . ?
F6 C44 C13 102.4(7) . . ?
F4' C44 C13 113.0(6) . . ?
F9' C45 F7' 104.9(7) . . ?
F9 C45 F8 104.4(6) . . ?
F9' C45 F8' 105.3(7) . . ?
F7' C45 F8' 102.3(7) . . ?
F9 C45 F7 100.3(6) . . ?
F8 C45 F7 100.7(6) . . ?
F9' C45 C34 115.9(7) . . ?
F9 C45 C34 118.2(5) . . ?
F7' C45 C34 117.2(7) . . ?
F8 C45 C34 117.1(5) . . ?
F8' C45 C34 109.9(6) . . ?
F7 C45 C34 113.4(5) . . ?
F10 C46 F11 104.7(7) . . ?
F12' C46 F10' 104.2(7) . . ?
F12' C46 F11' 104.3(6) . . ?
F10' C46 F11' 102.5(6) . . ?
F10 C46 F12 102.5(6) . . ?
F11 C46 F12 101.6(6) . . ?
F12' C46 C40 113.5(6) . . ?
F10 C46 C40 115.1(7) . . ?
F11 C46 C40 114.8(6) . . ?
F10' C46 C40 115.0(6) . . ?
F11' C46 C40 116.0(6) . . ?
F12 C46 C40 116.4(6) . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.064



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: d-DMSO'
