# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
# 
#######################################################################

data_Calix[4]triazolume_BF4
_database_code_depnum_ccdc_archive 'CCDC 2057514'
loop_
_audit_author_name
_audit_author_address
'Chang Seop Hong'
;Korea University
South Korea
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 N12, 4(B F4)'
_chemical_formula_sum            'C16 H24 B4 F16 N12'
_chemical_formula_weight         731.71

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 0.0014 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0174 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                   10.501(2)
_cell_length_b                   10.032(2)
_cell_length_c                   13.491(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.55(3)
_cell_angle_gamma                90
_cell_volume                     1362.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15747
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11442
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         33.512
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measured_fraction_theta_full 0.903
_diffrn_reflns_Laue_measured_fraction_max 0.773
_diffrn_reflns_Laue_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             4329
_reflns_number_gt                4101
_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       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX
_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)+(0.1270P)²+0.7188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.2099
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_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 0.41339(11) 0.54702(10) 0.79204(8) 0.0231(2) Uani 1 1 d . . . . .
B1 B 0.46254(16) 0.47090(14) 0.72581(11) 0.0148(3) Uani 1 1 d . . . . .
N1 N 0.21965(12) 0.27891(11) 0.52169(9) 0.0128(2) Uani 1 1 d . . . . .
C1 C 0.31598(13) 0.26261(11) 0.47341(10) 0.0122(2) Uani 1 1 d . . . . .
F2 F 0.42514(10) 0.33782(8) 0.72700(7) 0.0194(2) Uani 1 1 d . . . . .
B2 B 0.91020(17) 1.01828(16) 0.67238(13) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.15180(12) 0.38996(11) 0.49411(9) 0.0141(2) Uani 1 1 d . . . . .
C2 C 0.30579(13) 0.37216(12) 0.41081(10) 0.0142(2) Uani 1 1 d . . . . .
H2 H 0.356934 0.391764 0.366621 0.017 Uiso 1 1 calc R U . . .
C3 C 0.18092(15) 0.18920(14) 0.59418(11) 0.0179(3) Uani 1 1 d . . . . .
H3A H 0.119555 0.123769 0.556078 0.027 Uiso 1 1 calc R U . . .
H3B H 0.139478 0.239881 0.636831 0.027 Uiso 1 1 calc R U . . .
H3C H 0.258409 0.145345 0.636997 0.027 Uiso 1 1 calc R U . . .
F3 F 0.41714(10) 0.51804(9) 0.62389(7) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.20574(11) 0.44551(10) 0.42696(9) 0.0131(2) Uani 1 1 d . . . . .
N4 N 0.28286(12) 0.73701(11) 0.53195(9) 0.0142(2) Uani 1 1 d . . . . .
F4 F 0.60278(9) 0.48004(9) 0.75631(7) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.16457(14) 0.58129(12) 0.38786(11) 0.0162(3) Uani 1 1 d . . . . .
H4A H 0.082262 0.605015 0.402576 0.019 Uiso 1 1 calc R U . . .
H4AB H 0.149682 0.584098 0.313554 0.019 Uiso 1 1 calc R U . . .
F5 F 0.87495(14) 0.94621(18) 0.74754(13) 0.0504(5) Uani 1 1 d . . . . .
N5 N 0.39215(12) 0.80748(11) 0.56446(9) 0.0145(2) Uani 1 1 d . . . . .
C5 C 0.27115(13) 0.67779(12) 0.43924(10) 0.0127(2) Uani 1 1 d . . . . .
F6 F 0.80706(11) 1.01964(10) 0.58100(8) 0.0253(2) Uani 1 1 d . . . . .
N6 N 0.45160(12) 0.79378(10) 0.49095(9) 0.0127(2) Uani 1 1 d . . . . .
C6 C 0.38111(14) 0.71736(12) 0.41170(10) 0.0139(2) Uani 1 1 d . . . . .
H6 H 0.402721 0.696204 0.351345 0.017 Uiso 1 1 calc R U . . .
F7 F 0.93865(14) 1.14949(14) 0.70555(12) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.19239(16) 0.73027(17) 0.59725(13) 0.0226(3) Uani 1 1 d . . . . .
H7A H 0.107428 0.766126 0.560112 0.034 Uiso 1 1 calc R U . . .
H7B H 0.228590 0.781194 0.659129 0.034 Uiso 1 1 calc R U . . .
H7C H 0.182051 0.639103 0.615146 0.034 Uiso 1 1 calc R U . . .
C8 C 0.58571(13) 0.84926(12) 0.50751(11) 0.0147(2) Uani 1 1 d . . . . .
H8A H 0.606437 0.909046 0.566458 0.018 Uiso 1 1 calc R U . . .
H8AB H 0.589919 0.899532 0.447112 0.018 Uiso 1 1 calc R U . . .
F8 F 1.02252(11) 0.96170(11) 0.65303(9) 0.0278(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
F1 B1 1.3823(16) . ?
B1 F2 1.3931(16) . ?
B1 F3 1.4029(18) . ?
B1 F4 1.4146(19) . ?
N1 N2 1.3177(15) . ?
N1 C1 1.3601(15) . ?
N1 C3 1.4690(16) . ?
C1 C2 1.3716(17) . ?
C1 C8 1.4967(18) 3_666 ?
B2 F5 1.3792(18) . ?
B2 F6 1.390(2) . ?
B2 F7 1.395(2) . ?
B2 F8 1.3989(18) . ?
N2 N3 1.3208(14) . ?
C2 N3 1.3502(16) . ?
N3 C4 1.4800(17) . ?
N4 N5 1.3124(17) . ?
N4 C5 1.3584(16) . ?
N4 C7 1.4697(18) . ?
C4 C5 1.4927(19) . ?
N5 N6 1.3209(14) . ?
C5 C6 1.3687(18) . ?
N6 C6 1.3520(18) . ?
N6 C8 1.4709(17) . ?

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
F1 B1 F2 111.32(11) . . ?
F1 B1 F3 111.23(12) . . ?
F2 B1 F3 108.43(12) . . ?
F1 B1 F4 109.01(12) . . ?
F2 B1 F4 109.41(12) . . ?
F3 B1 F4 107.35(11) . . ?
N2 N1 C1 112.48(10) . . ?
N2 N1 C3 118.43(11) . . ?
C1 N1 C3 129.04(11) . . ?
N1 C1 C2 105.09(11) . . ?
N1 C1 C8 125.35(11) . 3_666 ?
C2 C1 C8 129.47(11) . 3_666 ?
F5 B2 F6 110.66(14) . . ?
F5 B2 F7 109.67(16) . . ?
F6 B2 F7 108.47(13) . . ?
F5 B2 F8 109.98(13) . . ?
F6 B2 F8 108.89(13) . . ?
F7 B2 F8 109.14(14) . . ?
N1 N2 N3 104.33(10) . . ?
N3 C2 C1 105.37(10) . . ?
N2 N3 C2 112.72(10) . . ?
N2 N3 C4 119.60(11) . . ?
C2 N3 C4 127.28(11) . . ?
N5 N4 C5 112.61(11) . . ?
N5 N4 C7 118.53(12) . . ?
C5 N4 C7 128.86(12) . . ?
N3 C4 C5 109.10(11) . . ?
N4 N5 N6 104.38(11) . . ?
N4 C5 C6 105.13(11) . . ?
N4 C5 C4 124.78(11) . . ?
C6 C5 C4 129.87(12) . . ?
N5 N6 C6 112.54(11) . . ?
N5 N6 C8 118.91(11) . . ?
C6 N6 C8 128.27(11) . . ?
N6 C6 C5 105.31(11) . . ?
N6 C8 C1 109.03(10) . 3_666 ?

_refine_diff_density_max         0.741
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.101


# start Validation Reply Form
_vrf_PLAT029_Calix4triazolume_BF4 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.903 Why?
RESPONSE: We measured SXRD using the synchrotron that leads to incomplete scans compare to actual symmetry.
;
# end Validation Reply Form
