# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1987380'
loop_
_audit_author_name
_audit_author_address
'shohei ajioka'
;gifu university
Japan
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'2-((E)-2-((E)-2-Chloro-3-(2-((E)-4,5,6,7-tetrafluoro-1,3,3-trimethylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-4,5,6,7-tetrafluoro-1,3,3-trimethyl-3H-indol-1-ium tetrafluoroborate'
_chemical_name_common            ?
_chemical_melting_point          238.0
_chemical_formula_moiety         'C32 H28 B Cl F12 N2'
_chemical_formula_sum            'C32 H28 B Cl F12 N2'
_chemical_formula_weight         714.82

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2949(3)
_cell_length_b                   27.7483(8)
_cell_length_c                   12.3186(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.464(3)
_cell_angle_gamma                90
_cell_volume                     3156.99(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13612
_cell_measurement_theta_min      2.3880
_cell_measurement_theta_max      29.5570

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.356
_oxdiff_exptl_absorpt_empirical_full_max 1.575
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax Mo'
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33500
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5855
_reflns_number_gt                4675
_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       'CrystalClear-SM Expert (Rigaku)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_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)+(0.0797P)²+1.3104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5855
_refine_ls_number_parameters     489
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.119
_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 0.7167(6) 0.4099(2) 0.2116(4) 0.0755(14) Uani 0.5 1 d . . P A 1
Cl2 Cl 0.6838(5) 0.40835(19) 0.1783(3) 0.0444(6) Uani 0.5 1 d . . P A 2
C1 C 0.6893(2) 0.34619(7) 0.19462(17) 0.0383(5) Uani 1 1 d . . . . .
C2 C 0.7947(2) 0.32114(7) 0.14478(16) 0.0350(4) Uani 1 1 d . . . . .
C3 C 0.7911(3) 0.26667(8) 0.1512(2) 0.0466(6) Uani 1 1 d . . . . .
H1 H 0.830515 0.253265 0.086184 0.037(11) Uiso 0.5 1 calc R . P B 1
H2 H 0.855321 0.256197 0.216497 0.036(11) Uiso 0.5 1 calc R . P B 1
H3 H 0.751322 0.253767 0.079072 0.14(3) Uiso 0.5 1 calc R . P C 2
H4 H 0.891434 0.254578 0.167152 0.067(16) Uiso 0.5 1 calc R . P C 2
C4 C 0.6435(5) 0.24602(15) 0.1571(4) 0.0379(10) Uani 0.5 1 d . . P D 1
H5 H 0.651976 0.211157 0.173712 0.045 Uiso 0.5 1 calc R U P D 1
H6 H 0.584863 0.249733 0.085365 0.045 Uiso 0.5 1 calc R U P D 1
C5 C 0.7043(7) 0.24821(18) 0.2346(7) 0.0704(19) Uani 0.5 1 d . . P D 2
H7 H 0.685079 0.213645 0.219178 0.084 Uiso 0.5 1 calc R U P D 2
H8 H 0.764222 0.250155 0.306139 0.084 Uiso 0.5 1 calc R U P D 2
C6 C 0.5666(3) 0.27138(8) 0.2457(2) 0.0486(6) Uani 1 1 d . . . . .
H9 H 0.462930 0.262276 0.235732 0.058 Uiso 0.5 1 calc R U P D 1
H10 H 0.608142 0.259254 0.318131 0.058 Uiso 0.5 1 calc R U P D 1
H11 H 0.531429 0.260613 0.314708 0.058 Uiso 0.5 1 calc R U P D 2
H12 H 0.494716 0.261130 0.184643 0.058 Uiso 0.5 1 calc R U P D 2
C7 C 0.5773(2) 0.32565(7) 0.24603(17) 0.0357(4) Uani 1 1 d . . . . .
C8 C 0.9031(2) 0.34522(7) 0.09724(16) 0.0366(5) Uani 1 1 d . . . . .
H13 H 0.891586 0.379059 0.088410 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0260(2) 0.32522(7) 0.06136(16) 0.0355(5) Uani 1 1 d . . . . .
H14 H 1.036709 0.291179 0.063901 0.043 Uiso 1 1 calc R U . . .
C10 C 1.1343(2) 0.35242(7) 0.02191(15) 0.0316(4) Uani 1 1 d . . . . .
C11 C 1.1385(2) 0.40707(7) 0.00426(16) 0.0345(4) Uani 1 1 d . . . . .
C12 C 1.1486(3) 0.43394(8) 0.11422(18) 0.0476(6) Uani 1 1 d . . . . .
H15 H 1.226828 0.420035 0.164537 0.071 Uiso 1 1 calc R U . . .
H16 H 1.056692 0.430775 0.145540 0.071 Uiso 1 1 calc R U . . .
H17 H 1.168692 0.468105 0.102568 0.071 Uiso 1 1 calc R U . . .
C13 C 1.0130(2) 0.42501(8) -0.07706(19) 0.0442(5) Uani 1 1 d . . . . .
H18 H 1.030325 0.458631 -0.096243 0.066 Uiso 1 1 calc R U . . .
H19 H 0.922300 0.422783 -0.043800 0.066 Uiso 1 1 calc R U . . .
H20 H 1.006171 0.405106 -0.143154 0.066 Uiso 1 1 calc R U . . .
C14 C 1.2812(2) 0.41211(7) -0.04313(16) 0.0364(5) Uani 1 1 d . . . . .
C15 C 1.3470(2) 0.36744(7) -0.04613(16) 0.0356(5) Uani 1 1 d . . . . .
N1 N 1.25790(18) 0.33266(6) -0.00538(13) 0.0341(4) Uani 1 1 d . . . . .
C16 C 1.2894(3) 0.28122(8) 0.0016(2) 0.0529(6) Uani 1 1 d . . . . .
H21 H 1.282470 0.269966 0.076226 0.079 Uiso 1 1 calc R U . . .
H22 H 1.387499 0.275408 -0.017449 0.079 Uiso 1 1 calc R U . . .
H23 H 1.219455 0.263713 -0.049320 0.079 Uiso 1 1 calc R U . . .
C17 C 1.3472(3) 0.45214(8) -0.08015(19) 0.0485(6) Uani 1 1 d . . . . .
C18 C 1.4786(3) 0.44752(10) -0.1218(2) 0.0569(7) Uani 1 1 d . . . . .
C19 C 1.5429(3) 0.40345(10) -0.12458(19) 0.0533(6) Uani 1 1 d . . . . .
C20 C 1.4792(2) 0.36276(9) -0.08624(18) 0.0447(5) Uani 1 1 d . . . . .
F1 F 1.28587(18) 0.49599(5) -0.07687(14) 0.0688(4) Uani 1 1 d . . . . .
B1 B 0.1621(4) 0.30827(10) 0.7059(3) 0.0581(7) Uani 1 1 d . U . . .
F2 F 1.54336(19) 0.48683(7) -0.15940(15) 0.0821(5) Uani 1 1 d . . . . .
F3 F 1.66999(16) 0.39927(7) -0.16541(14) 0.0799(5) Uani 1 1 d . . . . .
F4 F 1.54856(15) 0.32027(6) -0.09060(13) 0.0619(4) Uani 1 1 d . . . . .
C21 C 0.4851(2) 0.35388(7) 0.30120(17) 0.0383(5) Uani 1 1 d . . . . .
H24 H 0.514335 0.386359 0.314442 0.046 Uiso 1 1 calc R U . . .
C22 C 0.3561(2) 0.34052(7) 0.33918(16) 0.0357(5) Uani 1 1 d . . . . .
H25 H 0.319305 0.309145 0.322121 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2776(2) 0.37061(7) 0.40093(16) 0.0320(4) Uani 1 1 d . . . . .
C24 C 0.3317(2) 0.41590(7) 0.46463(16) 0.0325(4) Uani 1 1 d . . . . .
C25 C 0.4623(2) 0.40391(8) 0.54797(19) 0.0446(5) Uani 1 1 d . . . . .
H26 H 0.487231 0.432091 0.594240 0.067 Uiso 1 1 calc R U . . .
H27 H 0.545045 0.395154 0.509286 0.067 Uiso 1 1 calc R U . . .
H28 H 0.437934 0.376823 0.593585 0.067 Uiso 1 1 calc R U . . .
C26 C 0.3644(2) 0.45863(7) 0.39087(18) 0.0413(5) Uani 1 1 d . . . . .
H29 H 0.282743 0.463356 0.334250 0.062 Uiso 1 1 calc R U . . .
H30 H 0.452143 0.451726 0.356389 0.062 Uiso 1 1 calc R U . . .
H31 H 0.379043 0.487929 0.435168 0.062 Uiso 1 1 calc R U . . .
C27 C 0.1999(2) 0.42817(7) 0.52147(16) 0.0333(4) Uani 1 1 d . . . . .
C28 C 0.0898(2) 0.39569(7) 0.48998(16) 0.0315(4) Uani 1 1 d . . . . .
N2 N 0.13876(17) 0.36204(6) 0.41806(13) 0.0322(4) Uani 1 1 d . . . . .
C29 C 0.0484(2) 0.32287(8) 0.36840(18) 0.0421(5) Uani 1 1 d . . . . .
H32 H 0.094279 0.308906 0.307814 0.063 Uiso 1 1 calc R U . . .
H33 H -0.047185 0.335532 0.340861 0.063 Uiso 1 1 calc R U . . .
H34 H 0.037715 0.297950 0.423298 0.063 Uiso 1 1 calc R U . . .
C30 C -0.0432(2) 0.39924(7) 0.53016(18) 0.0379(5) Uani 1 1 d . . . . .
C31 C -0.0635(2) 0.43593(8) 0.60278(18) 0.0411(5) Uani 1 1 d . . . . .
C32 C 0.0440(2) 0.46848(8) 0.63297(17) 0.0416(5) Uani 1 1 d . . . . .
C33 C 0.1763(2) 0.46456(7) 0.59240(17) 0.0385(5) Uani 1 1 d . . . . .
F5 F -0.15323(13) 0.36852(5) 0.50251(12) 0.0539(4) Uani 1 1 d . . . . .
F6 F -0.19070(14) 0.43951(5) 0.64363(12) 0.0587(4) Uani 1 1 d . . . . .
F7 F 0.02032(16) 0.50438(5) 0.70291(11) 0.0571(4) Uani 1 1 d . . . . .
F8 F 0.28027(15) 0.49702(5) 0.62439(12) 0.0553(4) Uani 1 1 d . . . . .
F9 F 0.1811(6) 0.26317(19) 0.7471(5) 0.0713(14) Uani 0.5 1 d . U P E 1
F10 F 0.2425(7) 0.2747(2) 0.7586(6) 0.102(2) Uani 0.5 1 d . U P E 2
F11 F 0.0491(5) 0.3121(2) 0.7851(4) 0.1094(15) Uani 0.5 1 d . U P E 2
F12 F 0.1228(7) 0.3458(2) 0.7532(3) 0.0933(14) Uani 0.5 1 d . U P E 1
F13 F 0.2199(8) 0.3512(2) 0.7222(4) 0.1191(18) Uani 0.5 1 d . U P E 2
F14 F 0.3007(4) 0.31934(15) 0.6647(5) 0.1049(14) Uani 0.5 1 d . U P E 1
F15 F 0.08035(18) 0.30010(5) 0.60871(12) 0.0639(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.794(6) . ?
Cl2 C1 1.737(6) . ?
C1 C7 1.399(3) . ?
C1 C2 1.399(3) . ?
C2 C8 1.392(3) . ?
C2 C3 1.514(3) . ?
C3 C5 1.468(6) . ?
C3 C4 1.496(5) . ?
C3 H1 0.9900 . ?
C3 H2 0.9900 . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 C6 1.541(5) . ?
C4 H5 0.9900 . ?
C4 H6 0.9900 . ?
C5 C6 1.452(6) . ?
C5 H7 0.9900 . ?
C5 H8 0.9900 . ?
C6 C7 1.509(3) . ?
C6 H9 0.9900 . ?
C6 H10 0.9900 . ?
C6 H11 0.9900 . ?
C6 H12 0.9900 . ?
C7 C21 1.393(3) . ?
C8 C9 1.386(3) . ?
C8 H13 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H14 0.9500 . ?
C10 N1 1.350(2) . ?
C10 C11 1.533(3) . ?
C11 C14 1.515(3) . ?
C11 C13 1.532(3) . ?
C11 C12 1.540(3) . ?
C12 H15 0.9800 . ?
C12 H16 0.9800 . ?
C12 H17 0.9800 . ?
C13 H18 0.9800 . ?
C13 H19 0.9800 . ?
C13 H20 0.9800 . ?
C14 C17 1.372(3) . ?
C14 C15 1.384(3) . ?
C15 C20 1.381(3) . ?
C15 N1 1.401(2) . ?
N1 C16 1.458(3) . ?
C16 H21 0.9800 . ?
C16 H22 0.9800 . ?
C16 H23 0.9800 . ?
C17 F1 1.346(3) . ?
C17 C18 1.382(3) . ?
C18 F2 1.352(3) . ?
C18 C19 1.363(4) . ?
C19 F3 1.340(3) . ?
C19 C20 1.383(3) . ?
C20 F4 1.348(3) . ?
B1 F12 1.267(5) . ?
B1 F13 1.313(5) . ?
B1 F10 1.318(7) . ?
B1 F9 1.355(6) . ?
B1 F15 1.362(3) . ?
B1 F14 1.470(5) . ?
B1 F11 1.515(5) . ?
C21 C22 1.386(3) . ?
C21 H24 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H25 0.9500 . ?
C23 N2 1.352(2) . ?
C23 C24 1.536(3) . ?
C24 C27 1.516(3) . ?
C24 C25 1.536(3) . ?
C24 C26 1.545(3) . ?
C25 H26 0.9800 . ?
C25 H27 0.9800 . ?
C25 H28 0.9800 . ?
C26 H29 0.9800 . ?
C26 H30 0.9800 . ?
C26 H31 0.9800 . ?
C27 C33 1.369(3) . ?
C27 C28 1.386(3) . ?
C28 C30 1.386(3) . ?
C28 N2 1.398(2) . ?
N2 C29 1.465(3) . ?
C29 H32 0.9800 . ?
C29 H33 0.9800 . ?
C29 H34 0.9800 . ?
C30 F5 1.346(2) . ?
C30 C31 1.382(3) . ?
C31 F6 1.340(2) . ?
C31 C32 1.367(3) . ?
C32 F7 1.351(2) . ?
C32 C33 1.382(3) . ?
C33 F8 1.347(2) . ?

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
C7 C1 C2 126.16(19) . . ?
C7 C1 Cl2 116.3(2) . . ?
C2 C1 Cl2 117.1(2) . . ?
C7 C1 Cl1 116.8(2) . . ?
C2 C1 Cl1 116.3(2) . . ?
C8 C2 C1 121.48(18) . . ?
C8 C2 C3 121.52(18) . . ?
C1 C2 C3 116.89(17) . . ?
C5 C3 C2 113.7(3) . . ?
C4 C3 C2 114.3(2) . . ?
C4 C3 H1 108.7 . . ?
C2 C3 H1 108.7 . . ?
C4 C3 H2 108.7 . . ?
C2 C3 H2 108.7 . . ?
H1 C3 H2 107.6 . . ?
C5 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C5 C3 H4 108.8 . . ?
C2 C3 H4 108.8 . . ?
H3 C3 H4 107.7 . . ?
C3 C4 C6 111.1(3) . . ?
C3 C4 H5 109.4 . . ?
C6 C4 H5 109.4 . . ?
C3 C4 H6 109.4 . . ?
C6 C4 H6 109.4 . . ?
H5 C4 H6 108.0 . . ?
C6 C5 C3 118.1(5) . . ?
C6 C5 H7 107.8 . . ?
C3 C5 H7 107.8 . . ?
C6 C5 H8 107.8 . . ?
C3 C5 H8 107.8 . . ?
H7 C5 H8 107.1 . . ?
C5 C6 C7 112.5(3) . . ?
C7 C6 C4 114.9(2) . . ?
C7 C6 H9 108.5 . . ?
C4 C6 H9 108.5 . . ?
C7 C6 H10 108.5 . . ?
C4 C6 H10 108.5 . . ?
H9 C6 H10 107.5 . . ?
C5 C6 H11 109.1 . . ?
C7 C6 H11 109.1 . . ?
C5 C6 H12 109.1 . . ?
C7 C6 H12 109.1 . . ?
H11 C6 H12 107.8 . . ?
C21 C7 C1 121.43(18) . . ?
C21 C7 C6 121.20(18) . . ?
C1 C7 C6 117.24(18) . . ?
C9 C8 C2 127.11(19) . . ?
C9 C8 H13 116.4 . . ?
C2 C8 H13 116.4 . . ?
C8 C9 C10 123.34(18) . . ?
C8 C9 H14 118.3 . . ?
C10 C9 H14 118.3 . . ?
N1 C10 C9 122.50(17) . . ?
N1 C10 C11 109.30(16) . . ?
C9 C10 C11 128.19(17) . . ?
C14 C11 C13 110.68(16) . . ?
C14 C11 C10 100.56(15) . . ?
C13 C11 C10 112.61(17) . . ?
C14 C11 C12 108.96(17) . . ?
C13 C11 C12 112.61(18) . . ?
C10 C11 C12 110.74(16) . . ?
C11 C12 H15 109.5 . . ?
C11 C12 H16 109.5 . . ?
H15 C12 H16 109.5 . . ?
C11 C12 H17 109.5 . . ?
H15 C12 H17 109.5 . . ?
H16 C12 H17 109.5 . . ?
C11 C13 H18 109.5 . . ?
C11 C13 H19 109.5 . . ?
H18 C13 H19 109.5 . . ?
C11 C13 H20 109.5 . . ?
H18 C13 H20 109.5 . . ?
H19 C13 H20 109.5 . . ?
C17 C14 C15 120.0(2) . . ?
C17 C14 C11 130.3(2) . . ?
C15 C14 C11 109.67(17) . . ?
C20 C15 C14 120.5(2) . . ?
C20 C15 N1 130.5(2) . . ?
C14 C15 N1 109.04(17) . . ?
C10 N1 C15 111.32(16) . . ?
C10 N1 C16 123.66(17) . . ?
C15 N1 C16 124.94(17) . . ?
N1 C16 H21 109.5 . . ?
N1 C16 H22 109.5 . . ?
H21 C16 H22 109.5 . . ?
N1 C16 H23 109.5 . . ?
H21 C16 H23 109.5 . . ?
H22 C16 H23 109.5 . . ?
F1 C17 C14 121.0(2) . . ?
F1 C17 C18 119.3(2) . . ?
C14 C17 C18 119.7(2) . . ?
F2 C18 C19 120.1(2) . . ?
F2 C18 C17 119.9(3) . . ?
C19 C18 C17 120.0(2) . . ?
F3 C19 C18 119.6(2) . . ?
F3 C19 C20 119.2(2) . . ?
C18 C19 C20 121.2(2) . . ?
F4 C20 C15 123.1(2) . . ?
F4 C20 C19 118.4(2) . . ?
C15 C20 C19 118.5(2) . . ?
F13 B1 F10 111.4(5) . . ?
F12 B1 F9 128.2(5) . . ?
F12 B1 F15 112.3(3) . . ?
F13 B1 F15 117.6(3) . . ?
F10 B1 F15 123.0(4) . . ?
F9 B1 F15 102.3(3) . . ?
F12 B1 F14 107.2(4) . . ?
F9 B1 F14 103.9(4) . . ?
F15 B1 F14 98.9(3) . . ?
F13 B1 F11 98.0(4) . . ?
F10 B1 F11 97.3(4) . . ?
F15 B1 F11 102.7(3) . . ?
C22 C21 C7 128.12(19) . . ?
C22 C21 H24 115.9 . . ?
C7 C21 H24 115.9 . . ?
C21 C22 C23 123.44(18) . . ?
C21 C22 H25 118.3 . . ?
C23 C22 H25 118.3 . . ?
N2 C23 C22 123.26(18) . . ?
N2 C23 C24 109.10(16) . . ?
C22 C23 C24 127.56(17) . . ?
C27 C24 C25 111.02(16) . . ?
C27 C24 C23 100.66(15) . . ?
C25 C24 C23 110.65(17) . . ?
C27 C24 C26 108.79(16) . . ?
C25 C24 C26 111.50(17) . . ?
C23 C24 C26 113.72(16) . . ?
C24 C25 H26 109.5 . . ?
C24 C25 H27 109.5 . . ?
H26 C25 H27 109.5 . . ?
C24 C25 H28 109.5 . . ?
H26 C25 H28 109.5 . . ?
H27 C25 H28 109.5 . . ?
C24 C26 H29 109.5 . . ?
C24 C26 H30 109.5 . . ?
H29 C26 H30 109.5 . . ?
C24 C26 H31 109.5 . . ?
H29 C26 H31 109.5 . . ?
H30 C26 H31 109.5 . . ?
C33 C27 C28 119.45(18) . . ?
C33 C27 C24 131.03(18) . . ?
C28 C27 C24 109.52(17) . . ?
C30 C28 C27 120.93(19) . . ?
C30 C28 N2 129.86(18) . . ?
C27 C28 N2 109.21(16) . . ?
C23 N2 C28 111.46(16) . . ?
C23 N2 C29 125.30(17) . . ?
C28 N2 C29 123.24(16) . . ?
N2 C29 H32 109.5 . . ?
N2 C29 H33 109.5 . . ?
H32 C29 H33 109.5 . . ?
N2 C29 H34 109.5 . . ?
H32 C29 H34 109.5 . . ?
H33 C29 H34 109.5 . . ?
F5 C30 C31 118.34(18) . . ?
F5 C30 C28 123.21(19) . . ?
C31 C30 C28 118.44(19) . . ?
F6 C31 C32 119.8(2) . . ?
F6 C31 C30 119.3(2) . . ?
C32 C31 C30 120.90(18) . . ?
F7 C32 C31 119.61(18) . . ?
F7 C32 C33 120.2(2) . . ?
C31 C32 C33 120.15(19) . . ?
F8 C33 C27 121.21(18) . . ?
F8 C33 C32 118.66(18) . . ?
C27 C33 C32 120.13(19) . . ?

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
C7 C1 C2 C8 -179.0(2) . . . . ?
Cl2 C1 C2 C8 8.7(3) . . . . ?
Cl1 C1 C2 C8 -8.9(3) . . . . ?
C7 C1 C2 C3 -2.7(3) . . . . ?
Cl2 C1 C2 C3 -175.0(2) . . . . ?
Cl1 C1 C2 C3 167.4(2) . . . . ?
C8 C2 C3 C5 159.8(4) . . . . ?
C1 C2 C3 C5 -16.5(5) . . . . ?
C8 C2 C3 C4 -154.4(3) . . . . ?
C1 C2 C3 C4 29.4(4) . . . . ?
C2 C3 C4 C6 -49.5(4) . . . . ?
C2 C3 C5 C6 41.9(7) . . . . ?
C3 C5 C6 C7 -45.7(7) . . . . ?
C3 C4 C6 C7 45.3(4) . . . . ?
C2 C1 C7 C21 174.5(2) . . . . ?
Cl2 C1 C7 C21 -13.1(3) . . . . ?
Cl1 C1 C7 C21 4.5(3) . . . . ?
C2 C1 C7 C6 -1.5(3) . . . . ?
Cl2 C1 C7 C6 170.8(2) . . . . ?
Cl1 C1 C7 C6 -171.6(2) . . . . ?
C5 C6 C7 C21 -151.4(4) . . . . ?
C4 C6 C7 C21 163.6(3) . . . . ?
C5 C6 C7 C1 24.7(5) . . . . ?
C4 C6 C7 C1 -20.4(4) . . . . ?
C1 C2 C8 C9 168.8(2) . . . . ?
C3 C2 C8 C9 -7.3(3) . . . . ?
C2 C8 C9 C10 -175.2(2) . . . . ?
C8 C9 C10 N1 175.17(19) . . . . ?
C8 C9 C10 C11 -3.5(3) . . . . ?
N1 C10 C11 C14 3.2(2) . . . . ?
C9 C10 C11 C14 -178.05(19) . . . . ?
N1 C10 C11 C13 121.01(18) . . . . ?
C9 C10 C11 C13 -60.2(3) . . . . ?
N1 C10 C11 C12 -111.91(19) . . . . ?
C9 C10 C11 C12 66.9(3) . . . . ?
C13 C11 C14 C17 58.5(3) . . . . ?
C10 C11 C14 C17 177.7(2) . . . . ?
C12 C11 C14 C17 -65.8(3) . . . . ?
C13 C11 C14 C15 -121.52(19) . . . . ?
C10 C11 C14 C15 -2.3(2) . . . . ?
C12 C11 C14 C15 114.13(19) . . . . ?
C17 C14 C15 C20 0.0(3) . . . . ?
C11 C14 C15 C20 -179.99(18) . . . . ?
C17 C14 C15 N1 -179.32(19) . . . . ?
C11 C14 C15 N1 0.7(2) . . . . ?
C9 C10 N1 C15 178.10(18) . . . . ?
C11 C10 N1 C15 -3.0(2) . . . . ?
C9 C10 N1 C16 1.2(3) . . . . ?
C11 C10 N1 C16 -179.95(19) . . . . ?
C20 C15 N1 C10 -177.7(2) . . . . ?
C14 C15 N1 C10 1.5(2) . . . . ?
C20 C15 N1 C16 -0.9(3) . . . . ?
C14 C15 N1 C16 178.4(2) . . . . ?
C15 C14 C17 F1 -179.3(2) . . . . ?
C11 C14 C17 F1 0.7(4) . . . . ?
C15 C14 C17 C18 0.9(3) . . . . ?
C11 C14 C17 C18 -179.1(2) . . . . ?
F1 C17 C18 F2 -0.4(4) . . . . ?
C14 C17 C18 F2 179.4(2) . . . . ?
F1 C17 C18 C19 179.3(2) . . . . ?
C14 C17 C18 C19 -0.9(4) . . . . ?
F2 C18 C19 F3 -0.5(4) . . . . ?
C17 C18 C19 F3 179.8(2) . . . . ?
F2 C18 C19 C20 179.7(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C14 C15 C20 F4 179.6(2) . . . . ?
N1 C15 C20 F4 -1.2(4) . . . . ?
C14 C15 C20 C19 -0.9(3) . . . . ?
N1 C15 C20 C19 178.2(2) . . . . ?
F3 C19 C20 F4 0.6(3) . . . . ?
C18 C19 C20 F4 -179.6(2) . . . . ?
F3 C19 C20 C15 -178.9(2) . . . . ?
C18 C19 C20 C15 0.9(4) . . . . ?
C1 C7 C21 C22 167.7(2) . . . . ?
C6 C7 C21 C22 -16.4(4) . . . . ?
C7 C21 C22 C23 174.8(2) . . . . ?
C21 C22 C23 N2 165.30(19) . . . . ?
C21 C22 C23 C24 -18.3(3) . . . . ?
N2 C23 C24 C27 2.3(2) . . . . ?
C22 C23 C24 C27 -174.52(19) . . . . ?
N2 C23 C24 C25 119.76(18) . . . . ?
C22 C23 C24 C25 -57.1(3) . . . . ?
N2 C23 C24 C26 -113.84(18) . . . . ?
C22 C23 C24 C26 69.3(3) . . . . ?
C25 C24 C27 C33 62.0(3) . . . . ?
C23 C24 C27 C33 179.2(2) . . . . ?
C26 C24 C27 C33 -61.1(3) . . . . ?
C25 C24 C27 C28 -119.23(18) . . . . ?
C23 C24 C27 C28 -2.1(2) . . . . ?
C26 C24 C27 C28 117.71(19) . . . . ?
C33 C27 C28 C30 -0.7(3) . . . . ?
C24 C27 C28 C30 -179.62(18) . . . . ?
C33 C27 C28 N2 -179.91(18) . . . . ?
C24 C27 C28 N2 1.2(2) . . . . ?
C22 C23 N2 C28 175.18(18) . . . . ?
C24 C23 N2 C28 -1.8(2) . . . . ?
C22 C23 N2 C29 -5.0(3) . . . . ?
C24 C23 N2 C29 178.00(18) . . . . ?
C30 C28 N2 C23 -178.7(2) . . . . ?
C27 C28 N2 C23 0.4(2) . . . . ?
C30 C28 N2 C29 1.5(3) . . . . ?
C27 C28 N2 C29 -179.38(18) . . . . ?
C27 C28 C30 F5 -179.71(18) . . . . ?
N2 C28 C30 F5 -0.7(3) . . . . ?
C27 C28 C30 C31 -0.2(3) . . . . ?
N2 C28 C30 C31 178.87(19) . . . . ?
F5 C30 C31 F6 0.5(3) . . . . ?
C28 C30 C31 F6 -179.08(18) . . . . ?
F5 C30 C31 C32 -179.35(19) . . . . ?
C28 C30 C31 C32 1.1(3) . . . . ?
F6 C31 C32 F7 -0.8(3) . . . . ?
C30 C31 C32 F7 179.06(19) . . . . ?
F6 C31 C32 C33 179.02(19) . . . . ?
C30 C31 C32 C33 -1.1(3) . . . . ?
C28 C27 C33 F8 -179.56(18) . . . . ?
C24 C27 C33 F8 -0.9(3) . . . . ?
C28 C27 C33 C32 0.6(3) . . . . ?
C24 C27 C33 C32 179.3(2) . . . . ?
F7 C32 C33 F8 0.3(3) . . . . ?
C31 C32 C33 F8 -179.54(19) . . . . ?
F7 C32 C33 C27 -179.94(19) . . . . ?
C31 C32 C33 C27 0.3(3) . . . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / hexane'
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1987381'
loop_
_audit_author_name
_audit_author_address
'shohei ajioka'
;gifu university
Japan
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-((E)-2-((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium tetrafluoroborate'
_chemical_name_common            ?
_chemical_melting_point          244.9
_chemical_formula_moiety         'C32 H36 Cl N2, B F4'
_chemical_formula_sum            'C32 H36 B Cl F4 N2'
_chemical_formula_weight         570.89

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   31.542(4)
_cell_length_b                   7.8263(8)
_cell_length_c                   11.5946(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2862.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3643
_cell_measurement_theta_min      2.5680
_cell_measurement_theta_max      27.5690

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.883
_oxdiff_exptl_absorpt_empirical_full_max 1.160
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Mercury III ccd'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16438
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_point_group_measured_fraction_full 0.747
_reflns_number_total             3973
_reflns_number_gt                3179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.417
_reflns_Friedel_fraction_max     0.465
_reflns_Friedel_fraction_full    0.465

_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       'CrystalClear-SM Expert 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2016)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2016)'
_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)+(0.0656P)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_abs_structure_details 
;
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     367
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.003
_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
C1 C 0.31577(10) -0.1327(4) 0.2167(3) 0.0335(8) Uani 1 1 d . . . . .
C2 C 0.32116(12) -0.2464(5) 0.1273(4) 0.0421(9) Uani 1 1 d . . . . .
H1 H 0.3408 -0.2233 0.0671 0.051 Uiso 1 1 calc R U . . .
C3 C 0.29730(13) -0.3958(5) 0.1269(4) 0.0468(10) Uani 1 1 d . . . . .
H2 H 0.3005 -0.4752 0.0655 0.056 Uiso 1 1 calc R U . . .
C4 C 0.26880(13) -0.4302(5) 0.2151(4) 0.0487(11) Uani 1 1 d . . . . .
H3 H 0.2530 -0.5336 0.2138 0.058 Uiso 1 1 calc R U . . .
C5 C 0.26299(11) -0.3170(5) 0.3046(4) 0.0425(10) Uani 1 1 d . . . . .
H4 H 0.2433 -0.3393 0.3648 0.051 Uiso 1 1 calc R U . . .
C6 C 0.28713(10) -0.1689(4) 0.3032(3) 0.0328(8) Uani 1 1 d . . . . .
N1 N 0.28837(9) -0.0349(4) 0.3844(3) 0.0349(7) Uani 1 1 d . . . . .
C7 C 0.31682(10) 0.0841(4) 0.3563(3) 0.0330(8) Uani 1 1 d . . . . .
C8 C 0.33685(11) 0.0371(5) 0.2413(3) 0.0321(8) Uani 1 1 d . . . . .
C9 C 0.25987(12) -0.0296(5) 0.4837(4) 0.0480(10) Uani 1 1 d . . . . .
H5 H 0.2765 -0.0138 0.5544 0.072 Uiso 1 1 calc R U . . .
H6 H 0.2441 -0.1371 0.4885 0.072 Uiso 1 1 calc R U . . .
H7 H 0.2400 0.0657 0.4749 0.072 Uiso 1 1 calc R U . . .
C10 C 0.38501(11) 0.0165(5) 0.2452(4) 0.0440(9) Uani 1 1 d . . . . .
H8 H 0.3927 -0.0588 0.3094 0.066 Uiso 1 1 calc R U . . .
H9 H 0.3983 0.1286 0.2562 0.066 Uiso 1 1 calc R U . . .
H10 H 0.3949 -0.0334 0.1725 0.066 Uiso 1 1 calc R U . . .
C11 C 0.32445(12) 0.1698(5) 0.1509(3) 0.0412(9) Uani 1 1 d . . . . .
H11 H 0.3337 0.1311 0.0745 0.062 Uiso 1 1 calc R U . . .
H12 H 0.3381 0.2791 0.1691 0.062 Uiso 1 1 calc R U . . .
H13 H 0.2936 0.1845 0.1510 0.062 Uiso 1 1 calc R U . . .
C12 C 0.32361(11) 0.2292(5) 0.4252(3) 0.0375(9) Uani 1 1 d . . . . .
H14 H 0.3057 0.2435 0.4902 0.045 Uiso 1 1 calc R U . . .
C13 C 0.35392(11) 0.3521(5) 0.4067(3) 0.0357(8) Uani 1 1 d . . . . .
H15 H 0.3720 0.3379 0.3419 0.043 Uiso 1 1 calc R U . . .
C14 C 0.36041(11) 0.4978(5) 0.4761(3) 0.0332(8) Uani 1 1 d . . . . .
C15 C 0.32973(11) 0.5364(5) 0.5725(3) 0.0415(9) Uani 1 1 d . . . . .
H16 H 0.3040 0.5899 0.5396 0.050 Uiso 1 1 calc R U . . .
H17 H 0.3211 0.4279 0.6096 0.050 Uiso 1 1 calc R U . . .
C16 C 0.34813(12) 0.6535(5) 0.6627(3) 0.0441(10) Uani 1 1 d . . . . .
H18 H 0.3700 0.5912 0.7072 0.053 Uiso 1 1 calc R U . . .
H19 H 0.3255 0.6884 0.7169 0.053 Uiso 1 1 calc R U . . .
C17 C 0.36772(12) 0.8112(5) 0.6093(3) 0.0404(9) Uani 1 1 d . . . . .
H20 H 0.3452 0.8807 0.5726 0.048 Uiso 1 1 calc R U . . .
H21 H 0.3811 0.8812 0.6705 0.048 Uiso 1 1 calc R U . . .
C18 C 0.40068(11) 0.7646(4) 0.5201(3) 0.0332(8) Uani 1 1 d . . . . .
C19 C 0.39373(11) 0.6093(5) 0.4588(3) 0.0342(8) Uani 1 1 d . . . . .
Cl1 Cl 0.43059(3) 0.55842(14) 0.35086(10) 0.0564(3) Uani 1 1 d . . . . .
C20 C 0.43450(11) 0.8709(5) 0.4982(3) 0.0353(8) Uani 1 1 d . . . . .
H22 H 0.4548 0.8324 0.4435 0.042 Uiso 1 1 calc R U . . .
C21 C 0.44186(11) 1.0315(4) 0.5495(3) 0.0353(8) Uani 1 1 d . . . . .
H23 H 0.4217 1.0726 0.6035 0.042 Uiso 1 1 calc R U . . .
C22 C 0.47640(11) 1.1321(5) 0.5261(3) 0.0329(8) Uani 1 1 d . . . . .
N2 N 0.48309(9) 1.2863(4) 0.5792(3) 0.0345(7) Uani 1 1 d . . . . .
C23 C 0.45615(12) 1.3619(5) 0.6667(4) 0.0470(10) Uani 1 1 d . . . . .
H24 H 0.4264 1.3520 0.6431 0.071 Uiso 1 1 calc R U . . .
H25 H 0.4635 1.4828 0.6761 0.071 Uiso 1 1 calc R U . . .
H26 H 0.4603 1.3020 0.7400 0.071 Uiso 1 1 calc R U . . .
C24 C 0.52105(11) 1.3614(4) 0.5425(3) 0.0333(8) Uani 1 1 d . . . . .
C25 C 0.53928(12) 1.5152(5) 0.5772(4) 0.0412(9) Uani 1 1 d . . . . .
H27 H 0.5258 1.5876 0.6318 0.049 Uiso 1 1 calc R U . . .
C26 C 0.57800(13) 1.5578(5) 0.5286(4) 0.0464(10) Uani 1 1 d . . . . .
H28 H 0.5915 1.6608 0.5515 0.056 Uiso 1 1 calc R U . . .
C27 C 0.59737(12) 1.4545(5) 0.4481(4) 0.0473(10) Uani 1 1 d . . . . .
H29 H 0.6237 1.4880 0.4154 0.057 Uiso 1 1 calc R U . . .
C28 C 0.57874(12) 1.3024(5) 0.4146(4) 0.0452(10) Uani 1 1 d . . . . .
H36 H 0.5923 1.2303 0.3600 0.054 Uiso 1 1 calc R U . . .
C29 C 0.54007(11) 1.2568(4) 0.4615(3) 0.0354(8) Uani 1 1 d . . . . .
C30 C 0.51274(11) 1.1018(4) 0.4417(3) 0.0335(8) Uani 1 1 d . . . . .
C31 C 0.53764(12) 0.9381(5) 0.4693(4) 0.0457(10) Uani 1 1 d . . . . .
H30 H 0.5638 0.9356 0.4236 0.068 Uiso 1 1 calc R U . . .
H31 H 0.5203 0.8381 0.4504 0.068 Uiso 1 1 calc R U . . .
H32 H 0.5448 0.9361 0.5516 0.068 Uiso 1 1 calc R U . . .
C32 C 0.49683(13) 1.1001(5) 0.3164(3) 0.0439(10) Uani 1 1 d . . . . .
H33 H 0.4800 1.2032 0.3017 0.066 Uiso 1 1 calc R U . . .
H34 H 0.4792 0.9987 0.3038 0.066 Uiso 1 1 calc R U . . .
H35 H 0.5211 1.0972 0.2637 0.066 Uiso 1 1 calc R U . . .
B1 B 0.32713(16) 0.1651(7) 0.8023(4) 0.0486(12) Uani 1 1 d . . . . .
F1 F 0.36228(10) 0.2117(4) 0.7409(3) 0.0972(11) Uani 1 1 d . . . . .
F2 F 0.29484(11) 0.1349(6) 0.7267(3) 0.1072(12) Uani 1 1 d . . . . .
F3 F 0.33520(12) 0.0213(4) 0.8641(3) 0.0971(11) Uani 1 1 d . . . . .
F4 F 0.31485(10) 0.2957(4) 0.8738(3) 0.0813(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(5) . ?
C1 C6 1.379(5) . ?
C1 C8 1.513(5) . ?
C2 C3 1.390(6) . ?
C2 H1 0.9500 . ?
C3 C4 1.388(6) . ?
C3 H2 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H3 0.9500 . ?
C5 C6 1.387(5) . ?
C5 H4 0.9500 . ?
C6 N1 1.411(5) . ?
N1 C7 1.334(4) . ?
N1 C9 1.461(5) . ?
C7 C12 1.405(5) . ?
C7 C8 1.520(5) . ?
C8 C11 1.527(5) . ?
C8 C10 1.528(5) . ?
C9 H5 0.9800 . ?
C9 H6 0.9800 . ?
C9 H7 0.9800 . ?
C10 H8 0.9800 . ?
C10 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?
C11 H13 0.9800 . ?
C12 C13 1.373(5) . ?
C12 H14 0.9500 . ?
C13 C14 1.410(5) . ?
C13 H15 0.9500 . ?
C14 C19 1.380(5) . ?
C14 C15 1.509(5) . ?
C15 C16 1.507(5) . ?
C15 H16 0.9900 . ?
C15 H17 0.9900 . ?
C16 C17 1.513(5) . ?
C16 H18 0.9900 . ?
C16 H19 0.9900 . ?
C17 C18 1.511(5) . ?
C17 H20 0.9900 . ?
C17 H21 0.9900 . ?
C18 C20 1.376(5) . ?
C18 C19 1.426(5) . ?
C19 Cl1 1.754(3) . ?
C20 C21 1.410(5) . ?
C20 H22 0.9500 . ?
C21 C22 1.371(5) . ?
C21 H23 0.9500 . ?
C22 N2 1.371(4) . ?
C22 C30 1.525(5) . ?
N2 C24 1.400(4) . ?
N2 C23 1.450(5) . ?
C23 H24 0.9800 . ?
C23 H25 0.9800 . ?
C23 H26 0.9800 . ?
C24 C29 1.382(5) . ?
C24 C25 1.393(5) . ?
C25 C26 1.386(6) . ?
C25 H27 0.9500 . ?
C26 C27 1.378(6) . ?
C26 H28 0.9500 . ?
C27 C28 1.383(6) . ?
C27 H29 0.9500 . ?
C28 C29 1.383(5) . ?
C28 H36 0.9500 . ?
C29 C30 1.506(5) . ?
C30 C31 1.537(5) . ?
C30 C32 1.538(5) . ?
C31 H30 0.9800 . ?
C31 H31 0.9800 . ?
C31 H32 0.9800 . ?
C32 H33 0.9800 . ?
C32 H34 0.9800 . ?
C32 H35 0.9800 . ?
B1 F3 1.358(6) . ?
B1 F2 1.364(6) . ?
B1 F1 1.367(6) . ?
B1 F4 1.372(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.7(3) . . ?
C2 C1 C8 130.9(3) . . ?
C6 C1 C8 109.3(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H1 120.7 . . ?
C3 C2 H1 120.7 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H2 119.6 . . ?
C2 C3 H2 119.6 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H3 119.4 . . ?
C3 C4 H3 119.4 . . ?
C4 C5 C6 117.1(4) . . ?
C4 C5 H4 121.4 . . ?
C6 C5 H4 121.4 . . ?
C1 C6 C5 122.7(4) . . ?
C1 C6 N1 108.3(3) . . ?
C5 C6 N1 128.9(3) . . ?
C7 N1 C6 112.0(3) . . ?
C7 N1 C9 125.9(3) . . ?
C6 N1 C9 122.0(3) . . ?
N1 C7 C12 121.9(3) . . ?
N1 C7 C8 109.0(3) . . ?
C12 C7 C8 129.1(3) . . ?
C1 C8 C7 101.2(3) . . ?
C1 C8 C11 110.8(3) . . ?
C7 C8 C11 109.3(3) . . ?
C1 C8 C10 110.5(3) . . ?
C7 C8 C10 114.4(3) . . ?
C11 C8 C10 110.3(3) . . ?
N1 C9 H5 109.5 . . ?
N1 C9 H6 109.5 . . ?
H5 C9 H6 109.5 . . ?
N1 C9 H7 109.5 . . ?
H5 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
C8 C10 H8 109.5 . . ?
C8 C10 H9 109.5 . . ?
H8 C10 H9 109.5 . . ?
C8 C10 H10 109.5 . . ?
H8 C10 H10 109.5 . . ?
H9 C10 H10 109.5 . . ?
C8 C11 H11 109.5 . . ?
C8 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?
C8 C11 H13 109.5 . . ?
H11 C11 H13 109.5 . . ?
H12 C11 H13 109.5 . . ?
C13 C12 C7 125.7(4) . . ?
C13 C12 H14 117.1 . . ?
C7 C12 H14 117.1 . . ?
C12 C13 C14 125.3(4) . . ?
C12 C13 H15 117.3 . . ?
C14 C13 H15 117.3 . . ?
C19 C14 C13 122.6(3) . . ?
C19 C14 C15 118.0(3) . . ?
C13 C14 C15 119.4(3) . . ?
C16 C15 C14 112.9(3) . . ?
C16 C15 H16 109.0 . . ?
C14 C15 H16 109.0 . . ?
C16 C15 H17 109.0 . . ?
C14 C15 H17 109.0 . . ?
H16 C15 H17 107.8 . . ?
C15 C16 C17 111.7(3) . . ?
C15 C16 H18 109.3 . . ?
C17 C16 H18 109.3 . . ?
C15 C16 H19 109.3 . . ?
C17 C16 H19 109.3 . . ?
H18 C16 H19 107.9 . . ?
C18 C17 C16 111.4(3) . . ?
C18 C17 H20 109.4 . . ?
C16 C17 H20 109.4 . . ?
C18 C17 H21 109.4 . . ?
C16 C17 H21 109.4 . . ?
H20 C17 H21 108.0 . . ?
C20 C18 C19 122.9(3) . . ?
C20 C18 C17 120.9(3) . . ?
C19 C18 C17 116.2(3) . . ?
C14 C19 C18 125.7(3) . . ?
C14 C19 Cl1 117.7(3) . . ?
C18 C19 Cl1 116.6(3) . . ?
C18 C20 C21 126.1(3) . . ?
C18 C20 H22 117.0 . . ?
C21 C20 H22 117.0 . . ?
C22 C21 C20 124.0(3) . . ?
C22 C21 H23 118.0 . . ?
C20 C21 H23 118.0 . . ?
C21 C22 N2 122.6(3) . . ?
C21 C22 C30 129.4(3) . . ?
N2 C22 C30 108.0(3) . . ?
C22 N2 C24 111.4(3) . . ?
C22 N2 C23 125.7(3) . . ?
C24 N2 C23 122.9(3) . . ?
N2 C23 H24 109.5 . . ?
N2 C23 H25 109.5 . . ?
H24 C23 H25 109.5 . . ?
N2 C23 H26 109.5 . . ?
H24 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
C29 C24 C25 121.9(3) . . ?
C29 C24 N2 109.2(3) . . ?
C25 C24 N2 128.9(3) . . ?
C26 C25 C24 117.0(4) . . ?
C26 C25 H27 121.5 . . ?
C24 C25 H27 121.5 . . ?
C27 C26 C25 121.7(4) . . ?
C27 C26 H28 119.1 . . ?
C25 C26 H28 119.1 . . ?
C26 C27 C28 120.4(4) . . ?
C26 C27 H29 119.8 . . ?
C28 C27 H29 119.8 . . ?
C29 C28 C27 119.1(4) . . ?
C29 C28 H36 120.4 . . ?
C27 C28 H36 120.4 . . ?
C28 C29 C24 119.8(3) . . ?
C28 C29 C30 130.8(4) . . ?
C24 C29 C30 109.4(3) . . ?
C29 C30 C22 102.0(3) . . ?
C29 C30 C31 110.3(3) . . ?
C22 C30 C31 112.4(3) . . ?
C29 C30 C32 109.8(3) . . ?
C22 C30 C32 111.2(3) . . ?
C31 C30 C32 110.9(3) . . ?
C30 C31 H30 109.5 . . ?
C30 C31 H31 109.5 . . ?
H30 C31 H31 109.5 . . ?
C30 C31 H32 109.5 . . ?
H30 C31 H32 109.5 . . ?
H31 C31 H32 109.5 . . ?
C30 C32 H33 109.5 . . ?
C30 C32 H34 109.5 . . ?
H33 C32 H34 109.5 . . ?
C30 C32 H35 109.5 . . ?
H33 C32 H35 109.5 . . ?
H34 C32 H35 109.5 . . ?
F3 B1 F2 109.6(4) . . ?
F3 B1 F1 110.1(4) . . ?
F2 B1 F1 108.5(4) . . ?
F3 B1 F4 110.6(4) . . ?
F2 B1 F4 107.8(4) . . ?
F1 B1 F4 110.2(4) . . ?

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 0.0(5) . . . . ?
C8 C1 C2 C3 179.6(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C8 C1 C6 C5 -179.7(3) . . . . ?
C2 C1 C6 N1 178.8(3) . . . . ?
C8 C1 C6 N1 -0.9(4) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C4 C5 C6 N1 -178.2(4) . . . . ?
C1 C6 N1 C7 -1.2(4) . . . . ?
C5 C6 N1 C7 177.5(4) . . . . ?
C1 C6 N1 C9 176.4(3) . . . . ?
C5 C6 N1 C9 -4.9(6) . . . . ?
C6 N1 C7 C12 -179.8(3) . . . . ?
C9 N1 C7 C12 2.8(5) . . . . ?
C6 N1 C7 C8 2.8(4) . . . . ?
C9 N1 C7 C8 -174.7(3) . . . . ?
C2 C1 C8 C7 -177.3(4) . . . . ?
C6 C1 C8 C7 2.3(4) . . . . ?
C2 C1 C8 C11 66.8(5) . . . . ?
C6 C1 C8 C11 -113.6(3) . . . . ?
C2 C1 C8 C10 -55.8(5) . . . . ?
C6 C1 C8 C10 123.8(3) . . . . ?
N1 C7 C8 C1 -3.0(3) . . . . ?
C12 C7 C8 C1 179.7(3) . . . . ?
N1 C7 C8 C11 114.0(3) . . . . ?
C12 C7 C8 C11 -63.3(4) . . . . ?
N1 C7 C8 C10 -121.8(3) . . . . ?
C12 C7 C8 C10 61.0(5) . . . . ?
N1 C7 C12 C13 175.7(4) . . . . ?
C8 C7 C12 C13 -7.3(6) . . . . ?
C7 C12 C13 C14 179.7(4) . . . . ?
C12 C13 C14 C19 174.3(4) . . . . ?
C12 C13 C14 C15 -6.4(6) . . . . ?
C19 C14 C15 C16 -21.1(5) . . . . ?
C13 C14 C15 C16 159.7(4) . . . . ?
C14 C15 C16 C17 50.4(5) . . . . ?
C15 C16 C17 C18 -55.4(4) . . . . ?
C16 C17 C18 C20 -150.9(4) . . . . ?
C16 C17 C18 C19 31.1(5) . . . . ?
C13 C14 C19 C18 175.5(4) . . . . ?
C15 C14 C19 C18 -3.7(5) . . . . ?
C13 C14 C19 Cl1 -3.6(5) . . . . ?
C15 C14 C19 Cl1 177.2(3) . . . . ?
C20 C18 C19 C14 -179.6(4) . . . . ?
C17 C18 C19 C14 -1.7(5) . . . . ?
C20 C18 C19 Cl1 -0.5(5) . . . . ?
C17 C18 C19 Cl1 177.4(3) . . . . ?
C19 C18 C20 C21 175.3(4) . . . . ?
C17 C18 C20 C21 -2.5(6) . . . . ?
C18 C20 C21 C22 179.0(4) . . . . ?
C20 C21 C22 N2 -178.6(3) . . . . ?
C20 C21 C22 C30 2.0(6) . . . . ?
C21 C22 N2 C24 178.5(3) . . . . ?
C30 C22 N2 C24 -2.0(4) . . . . ?
C21 C22 N2 C23 1.4(5) . . . . ?
C30 C22 N2 C23 -179.1(3) . . . . ?
C22 N2 C24 C29 0.9(4) . . . . ?
C23 N2 C24 C29 178.1(3) . . . . ?
C22 N2 C24 C25 -178.8(4) . . . . ?
C23 N2 C24 C25 -1.6(6) . . . . ?
C29 C24 C25 C26 -1.2(5) . . . . ?
N2 C24 C25 C26 178.4(4) . . . . ?
C24 C25 C26 C27 1.1(6) . . . . ?
C25 C26 C27 C28 -1.0(6) . . . . ?
C26 C27 C28 C29 1.1(6) . . . . ?
C27 C28 C29 C24 -1.2(6) . . . . ?
C27 C28 C29 C30 180.0(4) . . . . ?
C25 C24 C29 C28 1.3(5) . . . . ?
N2 C24 C29 C28 -178.4(3) . . . . ?
C25 C24 C29 C30 -179.6(3) . . . . ?
N2 C24 C29 C30 0.6(4) . . . . ?
C28 C29 C30 C22 177.2(4) . . . . ?
C24 C29 C30 C22 -1.7(4) . . . . ?
C28 C29 C30 C31 57.6(5) . . . . ?
C24 C29 C30 C31 -121.3(3) . . . . ?
C28 C29 C30 C32 -64.8(5) . . . . ?
C24 C29 C30 C32 116.3(4) . . . . ?
C21 C22 C30 C29 -178.3(4) . . . . ?
N2 C22 C30 C29 2.2(4) . . . . ?
C21 C22 C30 C31 -60.2(5) . . . . ?
N2 C22 C30 C31 120.3(3) . . . . ?
C21 C22 C30 C32 64.8(5) . . . . ?
N2 C22 C30 C32 -114.7(3) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / hexane'
