# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1971747'
loop_
_audit_author_name
_audit_author_address
'Mane Jyothi'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-12-13 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H12 Br F6 N'
_chemical_formula_sum            'C23 H12 Br F6 N'
_chemical_formula_weight         496.25

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   15.327(4)
_cell_length_b                   9.854(2)
_cell_length_c                   28.274(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.113(9)
_cell_angle_gamma                90
_cell_volume                     4141.4(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4879
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      22.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.048
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_T_max  0.7912
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29508
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         26.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4256
_reflns_number_gt                2414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0688P)²+21.2989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Br1 Br -0.21501(6) 1.42393(7) -0.25866(2) 0.0824(4) Uani 1 1 d . . . . .
F7 F -0.0281(4) 0.4314(6) 0.1884(2) 0.130(2) Uani 1 1 d . . . . .
F8 F 0.0636(3) 0.2757(7) 0.2099(2) 0.149(3) Uani 1 1 d . . . . .
F9 F -0.0450(3) 0.2573(6) 0.14754(19) 0.1195(18) Uani 1 1 d . . . . .
F10 F 0.3483(4) 0.4203(11) 0.0966(3) 0.266(6) Uani 1 1 d . . . . .
F11 F 0.3564(4) 0.4093(11) 0.1661(4) 0.231(5) Uani 1 1 d . . . . .
F12 F 0.3259(4) 0.2509(7) 0.1299(4) 0.191(4) Uani 1 1 d . . . . .
C1 C -0.2048(4) 1.0007(6) -0.0636(2) 0.0617(17) Uani 1 1 d . . . . .
C1I C -0.1081(5) 1.2377(7) -0.1931(2) 0.0735(19) Uani 1 1 d . . . . .
H1I H -0.0640 1.2592 -0.2093 0.088 Uiso 1 1 calc R U . . .
C2N C -0.1914(4) 1.2954(6) -0.20743(19) 0.0541(15) Uani 1 1 d . . . . .
C3B C -0.2555(4) 1.2619(6) -0.1843(2) 0.0644(17) Uani 1 1 d . . . . .
H3B H -0.3124 1.3005 -0.1941 0.077 Uiso 1 1 calc R U . . .
C4O C -0.2368(4) 1.1705(6) -0.1461(2) 0.0553(15) Uani 1 1 d . . . . .
H4O H -0.2818 1.1486 -0.1305 0.066 Uiso 1 1 calc R U . . .
C5 C -0.1539(3) 1.1110(5) -0.13050(19) 0.0429(13) Uani 1 1 d . . . . .
C6X C -0.0893(4) 1.1472(7) -0.1545(2) 0.0687(18) Uani 1 1 d . . . . .
H6X H -0.0319 1.1103 -0.1445 0.082 Uiso 1 1 calc R U . . .
C7T C -0.1348(3) 1.0134(5) -0.08927(18) 0.0406(12) Uani 1 1 d . . . . .
C8K C -0.0586(4) 0.9427(5) -0.07522(18) 0.0432(12) Uani 1 1 d . . . . .
H8K H -0.0173 0.9608 -0.0936 0.052 Uiso 1 1 calc R U . . .
C9D C -0.0271(3) 0.8425(5) -0.03666(17) 0.0385(12) Uani 1 1 d . . . . .
C10 C -0.0780(4) 0.7855(6) -0.0071(2) 0.0579(16) Uani 1 1 d . . . . .
H10 H -0.1376 0.8117 -0.0111 0.070 Uiso 1 1 calc R U . . .
C11 C -0.0410(4) 0.6903(6) 0.0279(2) 0.0578(16) Uani 1 1 d . . . . .
H11 H -0.0770 0.6538 0.0469 0.069 Uiso 1 1 calc R U . . .
C12Q C 0.0469(3) 0.6473(5) 0.03592(18) 0.0393(12) Uani 1 1 d . . . . .
C13 C 0.0966(4) 0.7041(6) 0.0060(2) 0.0586(16) Uani 1 1 d . . . . .
H13 H 0.1563 0.6779 0.0099 0.070 Uiso 1 1 calc R U . . .
C14E C 0.0858(3) 0.5458(5) 0.07399(17) 0.0376(12) Uani 1 1 d . . . . .
C15U C 0.0368(4) 0.4892(6) 0.10442(19) 0.0479(13) Uani 1 1 d . . . . .
H15U H -0.0230 0.5144 0.1005 0.058 Uiso 1 1 calc R U . . .
C16Y C 0.0740(4) 0.3972(6) 0.14006(19) 0.0491(14) Uani 1 1 d . . . . .
C17H C 0.0179(4) 0.3399(8) 0.1719(2) 0.0673(19) Uani 1 1 d . . . . .
C18F C 0.1631(4) 0.3583(6) 0.14751(18) 0.0467(13) Uani 1 1 d . . . . .
H18F H 0.1887 0.2967 0.1719 0.056 Uiso 1 1 calc R U . . .
C19 C 0.2130(4) 0.4139(6) 0.1177(2) 0.0506(14) Uani 1 1 d . . . . .
C20 C 0.1754(4) 0.5042(6) 0.0819(2) 0.0496(14) Uani 1 1 d . . . . .
H20 H 0.2105 0.5392 0.0622 0.060 Uiso 1 1 calc R U . . .
C21Q C 0.3081(5) 0.3746(9) 0.1245(3) 0.084(2) Uani 1 1 d . . . . .
C45 C 0.0603(4) 0.7980(7) -0.0291(2) 0.0616(17) Uani 1 1 d . . . . .
H45 H 0.0960 0.8328 -0.0485 0.074 Uiso 1 1 calc R U . . .
N1 N -0.2626(4) 0.9955(7) -0.0442(3) 0.097(2) 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
Br1 C2N 1.892(6) . ?
F7 C17H 1.299(8) . ?
F8 C17H 1.295(7) . ?
F9 C17H 1.320(8) . ?
F10 C21Q 1.201(8) . ?
F11 C21Q 1.276(10) . ?
F12 C21Q 1.250(9) . ?
C1 N1 1.151(8) . ?
C1 C7T 1.440(8) . ?
C1I C2N 1.365(9) . ?
C1I C6X 1.384(8) . ?
C1I H1I 0.9300 . ?
C2N C3B 1.347(9) . ?
C3B C4O 1.383(8) . ?
C3B H3B 0.9300 . ?
C4O C5 1.371(7) . ?
C4O H4O 0.9300 . ?
C5 C6X 1.377(8) . ?
C5 C7T 1.485(7) . ?
C6X H6X 0.9300 . ?
C7T C8K 1.333(7) . ?
C8K C9D 1.463(7) . ?
C8K H8K 0.9300 . ?
C9D C45 1.376(7) . ?
C9D C10 1.392(7) . ?
C10 C11 1.382(8) . ?
C10 H10 0.9300 . ?
C11 C12Q 1.379(7) . ?
C11 H11 0.9300 . ?
C12Q C13 1.387(7) . ?
C12Q C14E 1.483(7) . ?
C13 C45 1.372(8) . ?
C13 H13 0.9300 . ?
C14E C15U 1.389(7) . ?
C14E C20 1.397(7) . ?
C15U C16Y 1.372(7) . ?
C15U H15U 0.9300 . ?
C16Y C18F 1.385(8) . ?
C16Y C17H 1.499(8) . ?
C18F C19 1.382(7) . ?
C18F H18F 0.9300 . ?
C19 C20 1.364(7) . ?
C19 C21Q 1.475(9) . ?
C20 H20 0.9300 . ?
C45 H45 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C7T 176.9(7) . . ?
C2N C1I C6X 120.2(6) . . ?
C2N C1I H1I 119.9 . . ?
C6X C1I H1I 119.9 . . ?
C3B C2N C1I 119.6(6) . . ?
C3B C2N Br1 120.6(5) . . ?
C1I C2N Br1 119.8(5) . . ?
C2N C3B C4O 120.1(6) . . ?
C2N C3B H3B 119.9 . . ?
C4O C3B H3B 119.9 . . ?
C5 C4O C3B 121.9(6) . . ?
C5 C4O H4O 119.0 . . ?
C3B C4O H4O 119.0 . . ?
C4O C5 C6X 116.9(5) . . ?
C4O C5 C7T 121.3(5) . . ?
C6X C5 C7T 121.8(5) . . ?
C5 C6X C1I 121.2(6) . . ?
C5 C6X H6X 119.4 . . ?
C1I C6X H6X 119.4 . . ?
C8K C7T C1 120.7(5) . . ?
C8K C7T C5 124.3(5) . . ?
C1 C7T C5 115.0(5) . . ?
C7T C8K C9D 132.9(5) . . ?
C7T C8K H8K 113.6 . . ?
C9D C8K H8K 113.6 . . ?
C45 C9D C10 116.4(5) . . ?
C45 C9D C8K 117.6(5) . . ?
C10 C9D C8K 126.0(5) . . ?
C11 C10 C9D 120.9(5) . . ?
C11 C10 H10 119.6 . . ?
C9D C10 H10 119.6 . . ?
C12Q C11 C10 122.6(5) . . ?
C12Q C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12Q C13 115.9(5) . . ?
C11 C12Q C14E 122.0(5) . . ?
C13 C12Q C14E 122.1(5) . . ?
C45 C13 C12Q 121.8(5) . . ?
C45 C13 H13 119.1 . . ?
C12Q C13 H13 119.1 . . ?
C15U C14E C20 116.1(5) . . ?
C15U C14E C12Q 122.5(5) . . ?
C20 C14E C12Q 121.3(5) . . ?
C16Y C15U C14E 122.0(5) . . ?
C16Y C15U H15U 119.0 . . ?
C14E C15U H15U 119.0 . . ?
C15U C16Y C18F 120.8(5) . . ?
C15U C16Y C17H 119.6(5) . . ?
C18F C16Y C17H 119.6(5) . . ?
F8 C17H F7 105.8(7) . . ?
F8 C17H F9 108.1(7) . . ?
F7 C17H F9 103.0(6) . . ?
F8 C17H C16Y 114.1(5) . . ?
F7 C17H C16Y 113.3(6) . . ?
F9 C17H C16Y 111.8(6) . . ?
C19 C18F C16Y 118.0(5) . . ?
C19 C18F H18F 121.0 . . ?
C16Y C18F H18F 121.0 . . ?
C20 C19 C18F 120.9(5) . . ?
C20 C19 C21Q 119.6(6) . . ?
C18F C19 C21Q 119.5(5) . . ?
C19 C20 C14E 122.1(5) . . ?
C19 C20 H20 118.9 . . ?
C14E C20 H20 118.9 . . ?
F10 C21Q F12 108.4(9) . . ?
F10 C21Q F11 103.3(10) . . ?
F12 C21Q F11 95.0(8) . . ?
F10 C21Q C19 117.7(6) . . ?
F12 C21Q C19 116.8(8) . . ?
F11 C21Q C19 112.5(8) . . ?
C13 C45 C9D 122.4(5) . . ?
C13 C45 H45 118.8 . . ?
C9D C45 H45 118.8 . . ?

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
C6X C1I C2N C3B -1.1(10) . . . . ?
C6X C1I C2N Br1 177.7(5) . . . . ?
C1I C2N C3B C4O 0.4(9) . . . . ?
Br1 C2N C3B C4O -178.4(5) . . . . ?
C2N C3B C4O C5 -0.1(9) . . . . ?
C3B C4O C5 C6X 0.5(9) . . . . ?
C3B C4O C5 C7T 179.7(5) . . . . ?
C4O C5 C6X C1I -1.2(9) . . . . ?
C7T C5 C6X C1I 179.6(6) . . . . ?
C2N C1I C6X C5 1.5(11) . . . . ?
C4O C5 C7T C8K 173.6(5) . . . . ?
C6X C5 C7T C8K -7.2(8) . . . . ?
C4O C5 C7T C1 -7.7(7) . . . . ?
C6X C5 C7T C1 171.5(6) . . . . ?
C1 C7T C8K C9D 2.0(9) . . . . ?
C5 C7T C8K C9D -179.3(5) . . . . ?
C7T C8K C9D C45 -173.9(6) . . . . ?
C7T C8K C9D C10 7.3(9) . . . . ?
C45 C9D C10 C11 0.5(9) . . . . ?
C8K C9D C10 C11 179.4(6) . . . . ?
C9D C10 C11 C12Q 0.4(10) . . . . ?
C10 C11 C12Q C13 -0.8(9) . . . . ?
C10 C11 C12Q C14E 179.5(6) . . . . ?
C11 C12Q C13 C45 0.4(9) . . . . ?
C14E C12Q C13 C45 -180.0(6) . . . . ?
C11 C12Q C14E C15U -1.0(8) . . . . ?
C13 C12Q C14E C15U 179.4(5) . . . . ?
C11 C12Q C14E C20 -179.4(5) . . . . ?
C13 C12Q C14E C20 0.9(8) . . . . ?
C20 C14E C15U C16Y -0.3(8) . . . . ?
C12Q C14E C15U C16Y -178.8(5) . . . . ?
C14E C15U C16Y C18F 0.9(9) . . . . ?
C14E C15U C16Y C17H 179.8(6) . . . . ?
C15U C16Y C17H F8 -167.2(7) . . . . ?
C18F C16Y C17H F8 11.7(10) . . . . ?
C15U C16Y C17H F7 -46.0(9) . . . . ?
C18F C16Y C17H F7 132.9(6) . . . . ?
C15U C16Y C17H F9 69.8(8) . . . . ?
C18F C16Y C17H F9 -111.3(6) . . . . ?
C15U C16Y C18F C19 -0.7(8) . . . . ?
C17H C16Y C18F C19 -179.6(6) . . . . ?
C16Y C18F C19 C20 0.0(8) . . . . ?
C16Y C18F C19 C21Q -179.8(6) . . . . ?
C18F C19 C20 C14E 0.6(9) . . . . ?
C21Q C19 C20 C14E -179.6(6) . . . . ?
C15U C14E C20 C19 -0.4(8) . . . . ?
C12Q C14E C20 C19 178.1(5) . . . . ?
C20 C19 C21Q F10 -2.9(14) . . . . ?
C18F C19 C21Q F10 176.9(10) . . . . ?
C20 C19 C21Q F12 -134.6(9) . . . . ?
C18F C19 C21Q F12 45.2(12) . . . . ?
C20 C19 C21Q F11 117.0(9) . . . . ?
C18F C19 C21Q F11 -63.2(11) . . . . ?
C12Q C13 C45 C9D 0.6(10) . . . . ?
C10 C9D C45 C13 -1.0(9) . . . . ?
C8K C9D C45 C13 -179.9(6) . . . . ?

_refine_diff_density_max         0.747
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.077

