# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1831917'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8tc04298e. 2018
_audit_update_record             
;
2018-03-23 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H12 Cl6 N'
_chemical_formula_sum            'C24 H11 Cl6 N2'
_chemical_formula_weight         540.05

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6879(5)
_cell_length_b                   8.2499(2)
_cell_length_c                   17.2222(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7570(10)
_cell_angle_gamma                90.00
_cell_volume                     2258.08(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    327
_cell_measurement_theta_min      4.5842
_cell_measurement_theta_max      27.2495

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.0500
_exptl_crystal_size_mid          0.0300
_exptl_crystal_size_min          0.0200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury2 (2x2 bin mode)
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25386
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         28.29
_reflns_number_total             5592
_reflns_number_gt                3293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0718P)²+1.2449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5592
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30351(7) 0.89322(12) 0.24686(5) 0.0676(3) Uani 1 1 d . . .
Cl2 Cl 0.20483(6) 0.28209(10) 0.36841(7) 0.0711(3) Uani 1 1 d . . .
Cl3 Cl 0.11023(6) 0.91669(10) 0.33933(7) 0.0743(3) Uani 1 1 d . . .
Cl4 Cl 0.27079(7) 0.64871(13) 0.53014(6) 0.0727(3) Uani 1 1 d . . .
Cl5 Cl 0.43713(7) 1.19981(12) 0.52870(7) 0.0776(3) Uani 1 1 d . . .
Cl6 Cl -0.09154(7) 0.46117(16) 0.39563(10) 0.1001(4) Uani 1 1 d . . .
C2 C 0.3049(2) 0.7933(4) 0.4743(2) 0.0491(7) Uani 1 1 d . . .
C1 C 0.28826(18) 0.7744(3) 0.38986(19) 0.0434(7) Uani 1 1 d . . .
C6 C 0.32266(19) 0.8950(4) 0.35133(19) 0.0465(7) Uani 1 1 d . . .
C3 C 0.3510(2) 0.9211(4) 0.5175(2) 0.0529(8) Uani 1 1 d . . .
H3A H 0.3612 0.9293 0.5736 0.063 Uiso 1 1 calc R . .
C4 C 0.3817(2) 1.0360(4) 0.4761(2) 0.0524(8) Uani 1 1 d . . .
C5 C 0.3689(2) 1.0244(4) 0.3934(2) 0.0513(8) Uani 1 1 d . . .
H5A H 0.3908 1.1019 0.3663 0.062 Uiso 1 1 calc R . .
C7 C 0.23640(19) 0.6431(3) 0.34434(18) 0.0437(7) Uani 1 1 d . . .
C8 C 0.15579(19) 0.5981(3) 0.35403(18) 0.0440(7) Uani 1 1 d . . .
C9 C 0.0942(2) 0.7137(4) 0.3559(2) 0.0531(8) Uani 1 1 d . . .
C12 C 0.0577(2) 0.3936(4) 0.3737(2) 0.0578(9) Uani 1 1 d . . .
H12A H 0.0451 0.2851 0.3788 0.069 Uiso 1 1 calc R . .
C13 C 0.1331(2) 0.4366(4) 0.3632(2) 0.0503(7) Uani 1 1 d . . .
C10 C 0.0189(2) 0.6737(4) 0.3680(2) 0.0636(10) Uani 1 1 d . . .
H10A H -0.0194 0.7540 0.3702 0.076 Uiso 1 1 calc R . .
C11 C 0.0011(2) 0.5128(5) 0.3768(2) 0.0630(9) Uani 1 1 d . . .
N1 N 0.26540(16) 0.5554(3) 0.28969(16) 0.0474(6) Uani 1 1 d . . .
C16 C 0.3494(3) 0.3977(4) 0.2369(3) 0.0653(10) Uani 1 1 d . . .
C15 C 0.3473(2) 0.4923(4) 0.3041(2) 0.0529(8) Uani 1 1 d . . .
C17 C 0.2672(3) 0.4057(4) 0.1788(2) 0.0692(11) Uani 1 1 d . . .
C18 C 0.2168(2) 0.5053(4) 0.2118(2) 0.0557(9) Uani 1 1 d . . .
C14 C 0.4173(2) 0.5058(5) 0.3722(3) 0.0660(10) Uani 1 1 d . . .
H14A H 0.4139 0.5656 0.4168 0.079 Uiso 1 1 calc R . .
C19 C 0.1358(3) 0.5479(5) 0.1679(2) 0.0708(11) Uani 1 1 d . . .
H19A H 0.1043 0.6150 0.1908 0.085 Uiso 1 1 calc R . .
N2 N 0.4916(2) 0.4324(5) 0.3746(3) 0.1029(14) Uani 1 1 d . . .
C20 C 0.1027(3) 0.4909(6) 0.0911(3) 0.0880(15) Uani 1 1 d . . .
H20A H 0.0481 0.5184 0.0607 0.106 Uiso 1 1 calc R . .
C23 C 0.4255(4) 0.3201(5) 0.2405(4) 0.0943(17) Uani 1 1 d . . .
H23A H 0.4295 0.2554 0.1976 0.113 Uiso 1 1 calc R . .
C21 C 0.1497(5) 0.3935(8) 0.0591(3) 0.119(2) Uani 1 1 d . . .
H21A H 0.1257 0.3562 0.0061 0.142 Uiso 1 1 calc R . .
C24 C 0.4935(4) 0.3417(7) 0.3083(5) 0.1052(18) Uani 1 1 d . . .
H24A H 0.5440 0.2922 0.3095 0.126 Uiso 1 1 calc R . .
C22 C 0.2310(4) 0.3458(7) 0.1001(3) 0.106(2) Uani 1 1 d . . .
H22A H 0.2605 0.2764 0.0761 0.127 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 C6 1.729(3) . ?
Cl2 C13 1.732(3) . ?
Cl3 C9 1.733(3) . ?
Cl4 C2 1.733(3) . ?
Cl5 C4 1.730(3) . ?
Cl6 C11 1.727(3) . ?
C2 C3 1.382(4) . ?
C2 C1 1.404(4) . ?
C1 C6 1.412(4) . ?
C1 C7 1.457(4) . ?
C6 C5 1.385(4) . ?
C3 C4 1.376(5) . ?
C4 C5 1.377(5) . ?
C7 N1 1.386(4) . ?
C7 C8 1.453(4) . ?
C8 C13 1.407(4) . ?
C8 C9 1.409(4) . ?
C9 C10 1.375(5) . ?
C12 C13 1.370(5) . ?
C12 C11 1.377(5) . ?
C10 C11 1.379(5) . ?
N1 C18 1.401(4) . ?
N1 C15 1.411(4) . ?
C16 C15 1.405(5) . ?
C16 C23 1.408(6) . ?
C16 C17 1.432(6) . ?
C15 C14 1.384(5) . ?
C17 C22 1.396(6) . ?
C17 C18 1.412(5) . ?
C18 C19 1.378(5) . ?
C14 N2 1.368(5) . ?
C19 C20 1.353(6) . ?
N2 C24 1.374(8) . ?
C20 C21 1.353(8) . ?
C23 C24 1.370(8) . ?
C21 C22 1.383(9) . ?

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
C3 C2 C1 123.0(3) . . ?
C3 C2 Cl4 116.7(3) . . ?
C1 C2 Cl4 120.3(2) . . ?
C2 C1 C6 115.4(3) . . ?
C2 C1 C7 122.5(3) . . ?
C6 C1 C7 122.1(3) . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 Cl1 116.6(2) . . ?
C1 C6 Cl1 120.7(2) . . ?
C4 C3 C2 118.7(3) . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 Cl5 119.3(3) . . ?
C5 C4 Cl5 119.1(3) . . ?
C4 C5 C6 118.7(3) . . ?
N1 C7 C8 118.2(3) . . ?
N1 C7 C1 118.7(3) . . ?
C8 C7 C1 123.1(3) . . ?
C13 C8 C9 114.5(3) . . ?
C13 C8 C7 123.0(3) . . ?
C9 C8 C7 122.4(3) . . ?
C10 C9 C8 123.1(3) . . ?
C10 C9 Cl3 116.8(3) . . ?
C8 C9 Cl3 120.0(2) . . ?
C13 C12 C11 119.3(3) . . ?
C12 C13 C8 123.3(3) . . ?
C12 C13 Cl2 116.7(2) . . ?
C8 C13 Cl2 119.8(2) . . ?
C9 C10 C11 119.1(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 Cl6 119.7(3) . . ?
C10 C11 Cl6 119.6(3) . . ?
C7 N1 C18 125.7(3) . . ?
C7 N1 C15 126.3(3) . . ?
C18 N1 C15 107.8(3) . . ?
C15 C16 C23 117.8(4) . . ?
C15 C16 C17 106.9(3) . . ?
C23 C16 C17 135.3(4) . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 N1 129.9(3) . . ?
C16 C15 N1 109.0(3) . . ?
C22 C17 C18 117.6(5) . . ?
C22 C17 C16 134.5(5) . . ?
C18 C17 C16 107.8(3) . . ?
C19 C18 N1 129.3(3) . . ?
C19 C18 C17 122.1(4) . . ?
N1 C18 C17 108.4(3) . . ?
N2 C14 C15 120.9(4) . . ?
C20 C19 C18 119.2(5) . . ?
C14 N2 C24 117.8(5) . . ?
C21 C20 C19 119.4(5) . . ?
C24 C23 C16 118.7(4) . . ?
C20 C21 C22 124.2(5) . . ?
C23 C24 N2 123.8(5) . . ?
C21 C22 C17 117.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.059
