# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1_120K
_database_code_depnum_ccdc_archive 'CCDC 2235772'
loop_
_audit_author_name
_audit_author_address
'Ramamoorthy Boomishankar'
;Professor in Chemistry, IISER Pune
India
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-05-24 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         ?
_chemical_formula_sum            'C6 H16 B F4 N'
_chemical_formula_weight         189.01

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'
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      tetragonal
_space_group_IT_number           77
_space_group_name_H-M_alt        'P 42'
_space_group_name_Hall           'P 4c'

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

_cell_length_a                   15.808(3)
_cell_length_b                   15.808(3)
_cell_length_c                   7.9627(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1989.9(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2605
_cell_measurement_theta_min      2.558
_cell_measurement_theta_max      22.513

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_density_meas      1.262
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.993
_exptl_transmission_factor_max   0.995
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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            38063
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         22.513
_diffrn_reflns_theta_full        22.513
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2607
_reflns_number_gt                2516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a merohedral twin in the lower symmetric
 tetragonal space group. Crystal were opaque and diffracted weakly 
 at higher angles. Hence 2theta = 45 degree cutoff was applied.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1025P)²+0.7300P] 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 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration 'Absolute structure can not be determined'
_refine_ls_number_reflns         2607
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2359
_refine_ls_wR_factor_gt          0.2317
_refine_ls_goodness_of_fit_ref   1.805
_refine_ls_restrained_S_all      1.804
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.008

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
F11 F 0.2652(6) 0.9424(6) 0.2292(13) 0.0667(14) Uani 1 1 d . . . . .
F12 F 0.3297(6) 1.0595(7) 0.1546(13) 0.0667(14) Uani 1 1 d . . . . .
F13 F 0.3922(6) 0.9383(7) 0.1104(13) 0.0667(14) Uani 1 1 d . . . . .
F14 F 0.3797(6) 0.9905(7) 0.3768(12) 0.0667(14) Uani 1 1 d . . . . .
F21 F 0.4211(5) 0.8457(6) 0.760(2) 0.089(4) Uani 1 1 d . . . . .
F22 F 0.5404(7) 0.8661(5) 0.6081(8) 0.055(3) Uani 1 1 d . . . . .
F23 F 0.5216(6) 0.7475(4) 0.7719(9) 0.048(2) Uani 1 1 d . . . . .
F24 F 0.5441(4) 0.8773(5) 0.8891(9) 0.0367(19) Uani 1 1 d . . . . .
N11 N 0.3398(6) 1.0014(6) 0.7355(13) 0.029(2) Uani 1 1 d . . . . .
H11A H 0.3686 0.9592 0.7880 0.044 Uiso 1 1 calc R U . . .
H11B H 0.3570 1.0523 0.7765 0.044 Uiso 1 1 calc R U . . .
H11C H 0.3501 0.9992 0.6231 0.044 Uiso 1 1 calc R U . . .
N21 N 0.5276(6) 0.8393(5) 0.2541(15) 0.029(2) Uani 1 1 d . . . . .
H21A H 0.5270 0.8459 0.3677 0.043 Uiso 1 1 calc R U . . .
H21B H 0.4892 0.8751 0.2069 0.043 Uiso 1 1 calc R U . . .
H21C H 0.5801 0.8514 0.2141 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2193(7) 0.9100(8) 0.6687(16) 0.0276(11) Uani 1 1 d . . . . .
H11D H 0.1580 0.9028 0.6786 0.041 Uiso 1 1 calc R U . . .
H11E H 0.2480 0.8605 0.7160 0.041 Uiso 1 1 calc R U . . .
H11F H 0.2346 0.9159 0.5500 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2471(7) 0.9909(7) 0.7663(17) 0.0276(11) Uani 1 1 d . . . . .
H12 H 0.2398 0.9787 0.8887 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1955(7) 1.0683(7) 0.7274(17) 0.0276(11) Uani 1 1 d . . . . .
C14 C 0.1974(8) 1.0900(8) 0.5402(14) 0.0276(11) Uani 1 1 d . . . . .
H14A H 0.1623 1.1400 0.5196 0.041 Uiso 1 1 calc R U . . .
H14B H 0.1754 1.0421 0.4753 0.041 Uiso 1 1 calc R U . . .
H14C H 0.2557 1.1018 0.5058 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2314(8) 1.1488(7) 0.8254(15) 0.0276(11) Uani 1 1 d . . . . .
H15A H 0.2218 1.1417 0.9461 0.041 Uiso 1 1 calc R U . . .
H15B H 0.2022 1.1998 0.7861 0.041 Uiso 1 1 calc R U . . .
H15C H 0.2922 1.1542 0.8039 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1051(7) 1.0539(7) 0.7824(15) 0.0276(11) Uani 1 1 d . . . . .
H16A H 0.0724 1.1060 0.7666 0.041 Uiso 1 1 calc R U . . .
H16B H 0.1041 1.0379 0.9013 0.041 Uiso 1 1 calc R U . . .
H16C H 0.0800 1.0084 0.7151 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4280(7) 0.7269(7) 0.3064(15) 0.026(3) Uani 1 1 d . . . . .
H21D H 0.4406 0.7285 0.4269 0.038 Uiso 1 1 calc R U . . .
H21E H 0.4093 0.6699 0.2753 0.038 Uiso 1 1 calc R U . . .
H21F H 0.3832 0.7676 0.2807 0.038 Uiso 1 1 calc R U . . .
C22 C 0.5049(7) 0.7487(7) 0.2104(15) 0.028(3) Uani 1 1 d . . . . .
H22 H 0.4900 0.7471 0.0884 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5849(7) 0.6900(6) 0.2373(17) 0.021(2) Uani 1 1 d . . . . .
C24 C 0.5592(8) 0.6028(9) 0.169(2) 0.058(5) Uani 1 1 d . . . . .
H24A H 0.5120 0.5805 0.2357 0.087 Uiso 1 1 calc R U . . .
H24B H 0.6074 0.5640 0.1768 0.087 Uiso 1 1 calc R U . . .
H24C H 0.5417 0.6082 0.0516 0.087 Uiso 1 1 calc R U . . .
C25 C 0.6583(8) 0.7200(7) 0.1351(15) 0.024(3) Uani 1 1 d . . . . .
H25A H 0.6897 0.7630 0.1982 0.036 Uiso 1 1 calc R U . . .
H25B H 0.6377 0.7446 0.0297 0.036 Uiso 1 1 calc R U . . .
H25C H 0.6957 0.6722 0.1102 0.036 Uiso 1 1 calc R U . . .
C26 C 0.6087(10) 0.6842(10) 0.4236(19) 0.048(4) Uani 1 1 d . . . . .
H26A H 0.5599 0.6643 0.4882 0.072 Uiso 1 1 calc R U . . .
H26B H 0.6258 0.7402 0.4643 0.072 Uiso 1 1 calc R U . . .
H26C H 0.6558 0.6445 0.4374 0.072 Uiso 1 1 calc R U . . .
B11 B 0.3413(15) 0.9804(14) 0.222(3) 0.0667(14) Uani 1 1 d . . . . .
B21 B 0.5057(11) 0.8357(9) 0.7561(19) 0.033(3) 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
F11 B11 1.35(3) . ?
F12 B11 1.37(2) . ?
F13 B11 1.37(2) . ?
F14 B11 1.38(2) . ?
F21 B21 1.35(2) . ?
F22 B21 1.386(17) . ?
F23 B21 1.421(17) . ?
F24 B21 1.387(18) . ?
N11 C12 1.495(15) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
N11 H11C 0.9100 . ?
N21 C22 1.517(15) . ?
N21 H21A 0.9100 . ?
N21 H21B 0.9100 . ?
N21 H21C 0.9100 . ?
C11 C12 1.559(16) . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C12 C13 1.503(16) . ?
C12 H12 1.0000 . ?
C13 C15 1.597(16) . ?
C13 C16 1.513(15) . ?
C13 C14 1.530(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 C22 1.476(16) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C22 C23 1.584(15) . ?
C22 H22 1.0000 . ?
C23 C24 1.537(19) . ?
C23 C26 1.53(2) . ?
C23 C25 1.495(16) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C12 N11 H11A 109.5 . . ?
C12 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C12 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
C22 N21 H21A 109.5 . . ?
C22 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
C22 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
C12 C11 H11D 109.5 . . ?
C12 C11 H11E 109.5 . . ?
H11D C11 H11E 109.5 . . ?
C12 C11 H11F 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
N11 C12 C11 106.6(9) . . ?
N11 C12 C13 114.0(9) . . ?
C11 C12 C13 114.3(9) . . ?
N11 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C15 C13 C16 108.3(9) . . ?
C15 C13 C12 110.8(9) . . ?
C16 C13 C12 109.3(9) . . ?
C15 C13 C14 106.9(9) . . ?
C16 C13 C14 109.5(10) . . ?
C12 C13 C14 111.9(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 H21D 109.5 . . ?
C22 C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
C22 C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C23 C22 N21 109.5(9) . . ?
C23 C22 C21 116.7(10) . . ?
N21 C22 C21 107.3(9) . . ?
C23 C22 H22 107.7 . . ?
N21 C22 H22 107.7 . . ?
C21 C22 H22 107.7 . . ?
C24 C23 C22 105.5(9) . . ?
C24 C23 C26 110.7(12) . . ?
C22 C23 C26 111.2(10) . . ?
C24 C23 C25 107.3(10) . . ?
C22 C23 C25 111.1(9) . . ?
C26 C23 C25 110.8(10) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F11 B11 F12 107.6(17) . . ?
F11 B11 F14 114.1(17) . . ?
F12 B11 F14 107.6(15) . . ?
F11 B11 F13 109.5(15) . . ?
F12 B11 F13 105.4(16) . . ?
F14 B11 F13 112.1(17) . . ?
F21 B21 F24 111.3(13) . . ?
F21 B21 F22 111.7(14) . . ?
F24 B21 F22 108.2(11) . . ?
F21 B21 F23 106.8(11) . . ?
F24 B21 F23 108.7(13) . . ?
F22 B21 F23 110.2(11) . . ?

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.097

# start Validation Reply Form
_vrf_THETM01_1_120K              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystal diffracted weakly at higher angles.
Hence 2theta = 45 degree cutoff was applied.
;
_vrf_PLAT340_1_120K              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0169 Ang.  
RESPONSE: This is likely related to the presence of heavy tertiary butyl groups.
;
# end Validation Reply Form


