# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_5_T240K_21CGC001
_database_code_depnum_ccdc_archive 'CCDC 2213757'
loop_
_audit_author_name
_audit_author_address
'Antonio L. Llamas-Saiz'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        'di-n-butylammonium tetrafluoroborate'
_chemical_name_common            'S2A_xyl - T240K'
_chemical_formula_moiety         'C8 H20 N, B F4'
_chemical_formula_sum            'C8 H20 B F4 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         217.06

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           67
_space_group_name_H-M_alt        'C m m a'
_space_group_name_Hall           '-C 2b 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'-x, y+1/2, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z'
'-x+1/2, y+1, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z'
'x, -y-1/2, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z'
'x+1/2, -y, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   7.5762(10)
_cell_length_b                   18.642(3)
_cell_length_c                   8.5564(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1208.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1333
_cell_measurement_theta_min      4.7443
_cell_measurement_theta_max      56.7234
_cell_measurement_temperature    240.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      240.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-III C14'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            13977
_diffrn_reflns_av_R_equivalents  0.1508
_diffrn_reflns_av_unetI/netI     0.1295
_diffrn_reflns_theta_min         5.17
_diffrn_reflns_theta_max         65.04
_diffrn_reflns_theta_full        65.04
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10

_refine_special_details          Twin

_reflns_number_total             629
_reflns_number_gt                368
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.1248
_refine_ls_wR_factor_gt          0.2748
_refine_ls_wR_factor_ref         0.3096
_refine_ls_goodness_of_fit_ref   1.551
_refine_ls_restrained_S_all      1.490
_refine_ls_number_reflns         629
_refine_ls_number_parameters     77
_refine_ls_number_restraints     96
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 2014.1 (Farrugia, 2012)'
_computing_publication_material  'IUCr Journals printCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0 0.75 0.2918(6) 0.0646(18) Uani d T P S 1 . .
H H1A 0.096043 0.75 0.353666 0.078 Uiso calc U P R 0.5 . .
H H1B -0.096043 0.75 0.353666 0.078 Uiso calc U P R 0.5 . .
C C2 0 0.6834(3) 0.1940(6) 0.0728(18) Uani d T P S 1 . .
H H2A 0.104587 0.683392 0.12662 0.087 Uiso calc U P R 0.5 . .
H H2B -0.104587 0.683392 0.126619 0.087 Uiso calc U P R 0.5 . .
C C3 0 0.6158(3) 0.2936(6) 0.0752(18) Uani d T P S 1 . .
H H3A -0.104715 0.615396 0.360804 0.09 Uiso calc U P R 0.5 . .
H H3B 0.104715 0.615396 0.360804 0.09 Uiso calc U P R 0.5 . .
C C4 0 0.5488(3) 0.1896(8) 0.096(2) Uani d T P S 1 . .
H H4A -0.104346 0.550335 0.122037 0.115 Uiso calc U P R 0.5 . .
H H4B 0.104346 0.550335 0.122038 0.115 Uiso calc U P R 0.5 . .
C C5 0 0.4790(3) 0.2765(9) 0.111(3) Uani d T P S 1 . .
H H5A 0 0.439637 0.202405 0.133 Uiso calc U P R 1 . .
H H5B 0.104538 0.476141 0.341612 0.133 Uiso calc U P R 0.5 . .
H H5C -0.104538 0.476141 0.341612 0.133 Uiso calc U P R 0.5 . .
B B1_1 0.495(4) 0.7502(15) 0.2852(10) 0.078(3) Uani d U P D 0.25 A -1
F F1_1 0.435(4) 0.7062(14) 0.171(2) 0.122(8) Uani d U P D 0.25 A -1
F F2_1 0.359(3) 0.7770(16) 0.375(3) 0.103(7) Uani d U P D 0.25 A -1
F F3_1 0.614(3) 0.7153(18) 0.382(2) 0.118(8) Uani d U P D 0.25 A -1
F F4_1 0.581(4) 0.8073(13) 0.221(3) 0.148(10) Uani d U P D 0.25 A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.057(4) 0.081(4) 0.056(4) 0 0 0
C2 0.077(4) 0.084(4) 0.057(4) 0 0 -0.003(2)
C3 0.074(4) 0.083(4) 0.069(4) 0 0 0.001(2)
C4 0.108(6) 0.085(4) 0.095(5) 0 0 -0.007(3)
C5 0.121(6) 0.083(5) 0.128(6) 0 0 -0.004(3)
B1_1 0.073(6) 0.104(7) 0.058(6) 0.003(9) -0.016(10) 0.010(10)
F1_1 0.130(16) 0.183(17) 0.053(6) -0.024(10) -0.010(6) -0.018(8)
F2_1 0.037(5) 0.147(15) 0.126(15) 0.002(5) -0.014(7) -0.004(8)
F3_1 0.101(12) 0.21(2) 0.041(7) 0.058(11) -0.006(7) 0.016(9)
F4_1 0.151(18) 0.109(10) 0.18(3) -0.026(9) 0.025(18) 0.021(15)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.497(6) ?
N1 C2 2_565 1.497(6) ?
N1 H1A . 0.9 ?
N1 H1B . 0.9 ?
C2 C3 . 1.522(7) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C4 . 1.533(7) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C4 C5 . 1.498(8) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C5 H5C . 0.97 ?
B1_1 F1_1 . 1.352(13) ?
B1_1 F4_1 . 1.360(15) ?
B1_1 F2_1 . 1.381(14) ?
B1_1 F3_1 . 1.384(13) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C2 . 2_565 112.1(6) ?
C2 N1 H1A . . 109.2 ?
C2 N1 H1A 2_565 . 109.2 ?
C2 N1 H1B . . 109.2 ?
C2 N1 H1B 2_565 . 109.2 ?
H1A N1 H1B . . 107.9 ?
N1 C2 C3 . . 112.0(5) ?
N1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 110.5(5) ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 114.8(6) ?
C5 C4 H4A . . 108.6 ?
C3 C4 H4A . . 108.6 ?
C5 C4 H4B . . 108.6 ?
C3 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.5 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
F1_1 B1_1 F4_1 . . 110.2(12) ?
F1_1 B1_1 F2_1 . . 111.5(18) ?
F4_1 B1_1 F2_1 . . 107.3(17) ?
F1_1 B1_1 F3_1 . . 111.4(17) ?
F4_1 B1_1 F3_1 . . 107.4(17) ?
F2_1 B1_1 F3_1 . . 108.8(9) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C2 C3 2_565 . . . 180.000(2) ?
N1 C2 C3 C4 . . . . 180.000(2) ?
C2 C3 C4 C5 . . . . 180.000(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A F2_1^a . 0.90 2.06 2.85(2) 146.3 ?
C2 H2A F1_1^a . 0.98 2.57 3.33(3) 134.5 ?

_shelx_res_file                  
;

TITL 21CGC001T240K_4 in Cmma
    21CGC001T240K_5.res
    created by SHELXL-2018/3 at 19:08:27 on 05-May-2021
CELL 1.54178   7.57620  18.64160   8.55640  90.0000  90.0000  90.0000
ZERR    4.00   0.00100   0.00260   0.00120   0.0000   0.0000   0.0000
LATT  7
SYMM -X, 0.5-Y, Z
SYMM -X, 0.5+Y, -Z
SYMM X, -Y, -Z
SFAC  C  H  B  N  F
UNIT 32 80 4 4 16
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -33.150
SIZE 0.084 0.221 0.319
MERG 0
ACTA
WPDB -2
RIGU
REM Restraints for Fragment bf4, Tetrafluoroborate, [BF4]- from: TURBOMOLE
REM V6.0 B-P86/def-SV(P). Please cite
REM https://doi.org/10.1107/S1600576718004508
SIMU_BF4 B1 > F4
RIGU_BF4 B1 > F4
SADI_BF4 0.02 B1 F1 B1 F2 B1 F3 B1 F4
SADI_BF4 0.04 F1 F2 F2 F3 F3 F4 F4 F1 F2 F4 F1 F3
SAME_BF4 B1 > F4
SIMU 0.04 0.08 1
L.S. 12
FMAP 2
PLAN 20
HTAB
REM Instructions for potential hydrogen bonds
HTAB N1 F2_1
HTAB C2 F1_1

BOND $H
CONF
WGHT    0.100000
BASF   0.23827   0.19626   0.08964
FVAR       0.78405
N1    4    0.000000    0.750000    0.291765    10.25000    0.05739    0.08097 =
         0.05558    0.00000    0.00000    0.00000
AFIX  23
H1A   2    0.096043    0.750000    0.353666    10.25000   -1.20000
H1B   2   -0.096043    0.750000    0.353666    10.25000   -1.20000
AFIX   0
C2    1    0.000000    0.683411    0.194016    10.50000    0.07713    0.08436 =
         0.05694   -0.00330    0.00000    0.00000
AFIX  23
H2A   2    0.104587    0.683392    0.126620    10.50000   -1.20000
H2B   2   -0.104587    0.683392    0.126619    10.50000   -1.20000
AFIX   0
C3    1    0.000000    0.615776    0.293568    10.50000    0.07431    0.08273 =
         0.06861    0.00112    0.00000    0.00000
AFIX  23
H3A   2   -0.104715    0.615396    0.360804    10.50000   -1.20000
H3B   2    0.104715    0.615396    0.360804    10.50000   -1.20000
AFIX   0
C4    1    0.000000    0.548787    0.189641    10.50000    0.10780    0.08476 =
         0.09513   -0.00667    0.00000    0.00000
AFIX  23
H4A   2   -0.104346    0.550335    0.122037    10.50000   -1.20000
H4B   2    0.104346    0.550335    0.122038    10.50000   -1.20000
AFIX   0
C5    1    0.000000    0.479033    0.276464    10.50000    0.12148    0.08296 =
         0.12806   -0.00373    0.00000    0.00000
REM AFIX 137
AFIX  33
H5A   2    0.000000    0.439637    0.202405    10.50000   -1.20000
H5B   2    0.104538    0.476141    0.341612    10.50000   -1.20000
H5C   2   -0.104538    0.476141    0.341612    10.50000   -1.20000
AFIX   0
RESI BF4 1
PART -1  10.25
B1    3    0.495322    0.750210    0.285168    10.25000    0.07259    0.10404 =
         0.05805    0.01034   -0.01629    0.00296
F1    5    0.435300    0.706237    0.171298    10.25000    0.12956    0.18291 =
         0.05296   -0.01788   -0.01029   -0.02435
F2    5    0.358762    0.776998    0.374776    10.25000    0.03694    0.14659 =
         0.12573   -0.00373   -0.01397    0.00222
F3    5    0.613691    0.715311    0.382145    10.25000    0.10149    0.21169 =
         0.04137    0.01623   -0.00603    0.05844
F4    5    0.580944    0.807254    0.221415    10.25000    0.15137    0.10882 =
         0.18486    0.02145    0.02524   -0.02582
PART 0
RESI 0
HKLF 5




REM  21CGC001T240K_4 in Cmma
REM wR2 = 0.309633, GooF = S = 1.55100, Restrained GooF = 1.49024 for all data
REM R1 = 0.124799 for 368 Fo > 4sig(Fo) and 0.169494 for all 629 data
REM 77 parameters refined using 96 restraints

END

WGHT      0.2000      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 F2_1
EQIV $3 -x+1/2, -y+3/2, -z+1
HTAB_1 N1_0 F2_$3
EQIV $4 -x+1/2, y, -z+1
HTAB_1 N1_0 F2_$4
EQIV $5 x, -y+3/2, z
HTAB_1 N1_0 F2_$5
EQIV $6 -x+1, -y+3/2, z
HTAB_1 N1_0 F3_$6
EQIV $7 x-1/2, y, -z+1
HTAB_1 N1_0 F3_$7
EQIV $8 x-1/2, -y+3/2, -z+1
HTAB_1 N1_0 F3_$8
EQIV $9 -x+1, y, z
HTAB_1 N1_0 F3_$9
EQIV $1 -x, -y+3/2, z
HTAB_1 N1_0 F2_$1
HTAB_1 N1_0 F2_$7
HTAB_1 N1_0 F2_$8
EQIV $2 -x, y, z
HTAB_1 N1_0 F2_$2
EQIV $10 x-1, y, z
HTAB_1 N1_0 F3_$10
HTAB_1 N1_0 F3_$3
HTAB_1 N1_0 F3_$4
EQIV $11 x-1, -y+3/2, z
HTAB_1 N1_0 F3_$11
HTAB C2 F1_1
EQIV $12 -x+1/2, y, -z
HTAB_1 C2_0 F1_$12
HTAB_1 C2_0 F4_$6
EQIV $13 x-1/2, y, -z
HTAB_1 C2_0 F1_$13
HTAB_1 C2_0 F1_$2
HTAB_1 C2_0 F4_$11

REM Highest difference peak  0.480,  deepest hole -0.278,  1-sigma level  0.081
Q1    1   0.0000  0.7500  0.1903  10.25000  0.05    0.48
Q2    1   0.0000  0.6366  0.2598  10.50000  0.05    0.39
Q3    1   0.0000  0.6750  0.3047  10.50000  0.05    0.38
Q4    1   0.0000  0.5482  0.3452  10.50000  0.05    0.25
Q5    1   0.3747  0.7500  0.2680  10.50000  0.05    0.24
Q6    1   0.0000  0.6164  0.3893  10.50000  0.05    0.23
Q7    1   0.0000  0.6821  0.1007  10.50000  0.05    0.23
Q8    1   0.0000  0.5037  0.2310  10.50000  0.05    0.20
Q9    1   0.0000  0.5573  0.1068  10.50000  0.05    0.19
Q10   1   0.6522  0.7191  0.4878  11.00000  0.05    0.19
Q11   1   0.0000  0.4911  0.3714  10.50000  0.05    0.17
Q12   1   0.3636  0.7500  0.3826  10.50000  0.05    0.15
Q13   1   0.5000  0.7500  0.1108  10.25000  0.05    0.15
Q14   1   0.2491  0.5674  0.1314  11.00000  0.05    0.14
Q15   1   0.2500  0.5000  0.0000  10.25000  0.05    0.14
Q16   1   0.1795  0.6297  0.4806  11.00000  0.05    0.14
Q17   1   0.2231  0.6304  0.0017  11.00000  0.05    0.13
Q18   1   0.1900  0.5000  0.5000  10.50000  0.05    0.12
Q19   1   0.0000  0.4433  0.3657  10.50000  0.05    0.12
Q20   1   0.0000  0.4200  0.2092  10.50000  0.05    0.11
;
_shelx_res_checksum              55693

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: p-xylene'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_6_T100K_21CGC001
_database_code_depnum_ccdc_archive 'CCDC 2213758'
loop_
_audit_author_name
_audit_author_address
'Antonio L. Llamas-Saiz'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        'di-n-butylammonium tetrafluoroborate'
_chemical_name_common            'S2A_xyl - T100K'
_chemical_formula_moiety         'C8 H20 N, B F4'
_chemical_formula_sum            'C8 H20 B F4 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         217.06

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, -z+1/2'
'-x, y, -z+1/2'
'-x+1/2, -y, z'
'x+1/2, y+1/2, z'
'x+1, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x+1, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y, z-1/2'
'x-1/2, y, -z'
'-x+1/2, -y+1/2, -z'
'-x, y+1/2, z-1/2'
'x+1/2, -y+1/2, z-1/2'
'x, y+1/2, -z'

_cell_length_a                   7.3980(5)
_cell_length_b                   18.4562(11)
_cell_length_c                   16.8535(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2301.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3334
_cell_measurement_theta_min      5.2508
_cell_measurement_theta_max      66.2287
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-III C14'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            50094
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         67.76
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20

_refine_special_details          Twin

_reflns_number_total             1100
_reflns_number_gt                791
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.1091
_refine_ls_wR_factor_gt          0.3093
_refine_ls_wR_factor_ref         0.3378
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_number_reflns         1100
_refine_ls_number_parameters     69
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1965P)²+1.9828P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 2014.1 (Farrugia, 2012)'
_computing_publication_material  'IUCr Journals printCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.25 0.5 0.3936(3) 0.0437(13) Uani d T P S 1 . .
H H1A 0.150903 0.497139 0.425483 0.052 Uiso calc U P R 0.5 . .
H H1B 0.349099 0.502862 0.425481 0.052 Uiso calc U P R 0.5 . .
C C2 0.2621(6) 0.4325(2) 0.3448(2) 0.0462(13) Uani d . . . 1 . .
H H2A 0.377401 0.432688 0.31501 0.055 Uiso calc U . R 1 . .
H H2B 0.162028 0.431994 0.305855 0.055 Uiso calc U . R 1 . .
C C3 0.2523(5) 0.3646(2) 0.3955(2) 0.0466(12) Uani d . . . 1 . .
H H3A 0.13971 0.365241 0.42721 0.056 Uiso calc U . R 1 . .
H H3B 0.355997 0.363568 0.432592 0.056 Uiso calc U . R 1 . .
C C4 0.2558(6) 0.2970(2) 0.3431(3) 0.0527(13) Uani d . . . 1 . .
H H4A 0.150434 0.29826 0.306953 0.063 Uiso calc U . R 1 . .
H H4B 0.366387 0.298045 0.310068 0.063 Uiso calc U . R 1 . .
C C5 0.2519(6) 0.2261(2) 0.3896(3) 0.0586(13) Uani d . . . 1 . .
H H5A 0.251411 0.18523 0.352484 0.088 Uiso calc U . R 1 . .
H H5B 0.142738 0.224447 0.422459 0.088 Uiso calc U . R 1 . .
H H5C 0.359018 0.22316 0.423618 0.088 Uiso calc U . R 1 . .
B B1 0.25 0.5 0.6051(4) 0.0470(17) Uani d T P S 1 . .
F F1 0.3436(4) 0.45154(15) 0.65198(16) 0.0675(11) Uani d . . . 1 . .
F F2 0.1258(3) 0.46344(15) 0.55644(14) 0.0578(10) Uani d . . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.039(3) 0.060(3) 0.032(3) 0.000(2) 0 0
C2 0.044(2) 0.059(3) 0.036(3) 0.0033(18) -0.0002(15) -0.0038(15)
C3 0.044(2) 0.056(3) 0.039(2) -0.0006(17) 0.0011(16) -0.0018(16)
C4 0.052(3) 0.056(3) 0.050(3) -0.0012(19) -0.0014(18) -0.0043(17)
C5 0.057(3) 0.057(3) 0.062(3) -0.003(2) -0.002(2) -0.002(2)
B1 0.054(4) 0.050(4) 0.038(4) 0.008(3) 0 0
F1 0.068(2) 0.075(2) 0.060(2) 0.0009(13) -0.0135(12) 0.0106(12)
F2 0.0524(17) 0.079(2) 0.0417(17) -0.0069(11) -0.0003(10) -0.0022(11)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 4_565 1.495(5) ?
N1 C2 . 1.495(5) ?
N1 H1A . 0.91 ?
N1 H1B . 0.91 ?
C2 C3 . 1.518(5) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.530(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.524(6) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
B1 F1 . 1.380(5) ?
B1 F1 4_565 1.380(5) ?
B1 F2 . 1.404(5) ?
B1 F2 4_565 1.404(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C2 4_565 . 113.2(4) ?
C2 N1 H1A 4_565 . 108.9 ?
C2 N1 H1A . . 108.9 ?
C2 N1 H1B 4_565 . 108.9 ?
C2 N1 H1B . . 108.9 ?
H1A N1 H1B . . 107.7 ?
N1 C2 C3 . . 112.0(3) ?
N1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 110.4(3) ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3B . . 109.6 ?
C4 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 113.8(4) ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
F1 B1 F1 . 4_565 110.1(5) ?
F1 B1 F2 . . 110.56(16) ?
F1 B1 F2 4_565 . 108.52(17) ?
F1 B1 F2 . 4_565 108.52(17) ?
F1 B1 F2 4_565 4_565 110.56(16) ?
F2 B1 F2 . 4_565 108.5(5) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C2 C3 4_565 . . . -173.4(4) ?
N1 C2 C3 C4 . . . . 177.2(3) ?
C2 C3 C4 C5 . . . . 178.3(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A F2 . 0.91 2.30 2.971(5) 130.3 ?
N1 H1A F2 9_566 0.91 2.19 2.982(3) 144.5 ?
C2 H2B F1 10_655 0.99 2.62 3.361(5) 131.9 ?
C2 H2B F1 12_556 0.99 2.49 3.116(5) 121.2 ?

_shelx_res_file                  
;

TITL 21CGC001T100K_5.res in Ccca
    21CGC001T100K__1dom_5.res
    created by SHELXL-2018/3 at 18:12:36 on 05-May-2021
CELL 1.54178   7.39800  18.45620  16.85350  90.0000  90.0000  90.0000
ZERR    8.00   0.00050   0.00110   0.00100   0.0000   0.0000   0.0000
LATT 7
SYMM x+1/2, -y, -z+1/2
SYMM -x, y, -z+1/2
SYMM -x+1/2, -y, z
SFAC C H N B F
UNIT 64 160 8 8 32
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173.150
SIZE 0.084 0.221 0.319
MERG 0
ACTA
WPDB -2
REM TWST 0
L.S. 14
FMAP 2
PLAN 14
HTAB
REM Instructions for potential hydrogen bonds
HTAB N1 F2
EQIV $1 -x, -y+1, -z+1
HTAB N1 F2_$1
EQIV $2 -x+1/2, y, z-1/2
HTAB C2 F1_$2
EQIV $3 x-1/2, y, -z+1
HTAB C2 F1_$3

BOND $H
CONF
WGHT    0.196500    1.982800
BASF   0.26637   0.13687   0.11231
FVAR       0.38248
N1    3    0.250000    0.500000    0.393648    10.50000    0.03876    0.06018 =
         0.03207    0.00000    0.00000   -0.00004
AFIX  23
H1A   2    0.150903    0.497139    0.425483    10.50000   -1.20000
H1B   2    0.349099    0.502862    0.425481    10.50000   -1.20000
AFIX   0
C2    1    0.262120    0.432545    0.344840    11.00000    0.04427    0.05881 =
         0.03563   -0.00384   -0.00024    0.00332
AFIX  23
H2A   2    0.377401    0.432688    0.315010    11.00000   -1.20000
H2B   2    0.162028    0.431994    0.305855    11.00000   -1.20000
AFIX   0
C3    1    0.252311    0.364648    0.395475    11.00000    0.04423    0.05633 =
         0.03914   -0.00181    0.00108   -0.00058
AFIX  23
H3A   2    0.139710    0.365241    0.427210    11.00000   -1.20000
H3B   2    0.355997    0.363568    0.432592    11.00000   -1.20000
AFIX   0
C4    1    0.255811    0.296961    0.343132    11.00000    0.05236    0.05596 =
         0.04963   -0.00435   -0.00138   -0.00124
AFIX  23
H4A   2    0.150434    0.298260    0.306953    11.00000   -1.20000
H4B   2    0.366387    0.298045    0.310068    11.00000   -1.20000
AFIX   0
C5    1    0.251895    0.226129    0.389567    11.00000    0.05724    0.05676 =
         0.06185   -0.00243   -0.00200   -0.00272
AFIX 137
H5A   2    0.251411    0.185230    0.352484    11.00000   -1.50000
H5B   2    0.142738    0.224447    0.422459    11.00000   -1.50000
H5C   2    0.359018    0.223160    0.423618    11.00000   -1.50000
AFIX   0
B1    4    0.250000    0.500000    0.605111    10.50000    0.05350    0.04960 =
         0.03785    0.00000    0.00000    0.00776
F1    5    0.343615    0.451538    0.651983    11.00000    0.06796    0.07458 =
         0.05990    0.01056   -0.01349    0.00090
F2    5    0.125848    0.463440    0.556443    11.00000    0.05243    0.07928 =
         0.04174   -0.00220   -0.00028   -0.00687
HKLF 5




REM  21CGC001T100K_5.res in Ccca
REM wR2 = 0.337774, GooF = S = 1.14005, Restrained GooF = 1.14005 for all data
REM R1 = 0.109081 for 791 Fo > 4sig(Fo) and 0.130992 for all 1100 data
REM 69 parameters refined using 0 restraints

END

WGHT      0.1965      1.9829

REM Instructions for potential hydrogen bonds
HTAB N1 F2
HTAB N1 F2_$1
EQIV $4 -x+1/2, -y+1, z
HTAB N1 F2_$4
EQIV $5 x+1/2, y, -z+1
HTAB N1 F2_$5
HTAB C2 F1_$2
HTAB C2 F1_$3

REM Highest difference peak  0.610,  deepest hole -0.318,  1-sigma level  0.113
Q1    1   0.1130  0.5346  0.5579  11.00000  0.05    0.61
Q2    1   0.2550  0.4326  0.3957  11.00000  0.05    0.60
Q3    1   0.2500  0.5000  0.3415  10.50000  0.05    0.58
Q4    1   0.2517  0.3004  0.3953  11.00000  0.05    0.54
Q5    1   0.2535  0.3615  0.3464  11.00000  0.05    0.51
Q6    1   0.1178  0.4694  0.6175  11.00000  0.05    0.43
Q7    1   0.2474  0.2527  0.3600  11.00000  0.05    0.39
Q8    1   0.2832  0.4528  0.6010  11.00000  0.05    0.38
Q9    1   0.3449  0.4563  0.7161  11.00000  0.05    0.38
Q10   1   0.1252  0.4113  0.5601  11.00000  0.05    0.37
Q11   1   0.1246  0.4720  0.5004  11.00000  0.05    0.36
Q12   1   0.2906  0.3665  0.4403  11.00000  0.05    0.25
Q13   1   0.2696  0.4392  0.2842  11.00000  0.05    0.22
Q14   1   0.0516  0.2175  0.4804  11.00000  0.05    0.20
;
_shelx_res_checksum              63062

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: p-xylene'
_chemical_properties_physical    Hygroscopic
