# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ala-oh-bf4
_database_code_depnum_ccdc_archive 'CCDC 2247731'
loop_
_audit_author_name
_audit_author_address
'Tamara Bednarchuk'
;Institute of Low Temperature and Structure Research, Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2023-03-10 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 N2 O2, B F4'
_chemical_formula_sum            'C8 H11 B F4 N2 O2'
_chemical_formula_weight         254.00
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.355(3)
_cell_length_b                   8.831(3)
_cell_length_c                   11.415(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.79(3)
_cell_angle_gamma                90
_cell_volume                     539.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6360
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.691
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_min         2.916
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  57.00   1.00   20.00    --   13.31 -99.00-120.00   82
  2  ω    -78.00 -32.00   1.00   20.00    --   13.31 178.00 120.00   46
  3  ω    -92.00  18.00   1.00   20.00    --  -14.40 -57.00 -30.00  110
  4  ω    -94.00  17.00   1.00   20.00    --  -14.40 -37.00  60.00  111
  5  ω    -98.00  22.00   1.00   20.00    --  -14.40 -77.00-150.00  120
  6  ω    -47.00  64.00   1.00   20.00    --  -14.40  57.00 120.00  111
  7  ω    -55.00  34.00   1.00   20.00    --  -14.40  91.00 -84.35   89
  8  ω    -25.00  57.00   1.00   20.00    --   13.31 -99.00 120.00   82
  9  ω    -78.00 -33.00   1.00   20.00    --   13.31 178.00-180.00   45
 10  ω     39.00  50.00   1.00   20.00    --   13.31-142.00  82.00   11
 11  ω    -21.00  33.00   1.00   20.00    --  -14.40  92.00 109.36   54
 12  ω    -79.00 -34.00   1.00   20.00    --   13.31   0.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1909
_reflns_number_total             2063
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.3569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11), C13(H13), C15(H15), C16(H16), C12(H12)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.2498(5) 0.4586(3) 0.5477(2) 0.0183(6) Uani 1 1 d . . . . .
O1 O 0.2870(4) 0.6799(3) 0.4555(3) 0.0218(6) Uani 1 1 d . . . . .
F1 F 0.7029(6) 0.4722(4) 0.2172(3) 0.0477(8) Uani 1 1 d . . . . .
F2 F 0.9755(6) 0.3527(4) 0.0987(3) 0.0504(9) Uani 1 1 d . . . . .
N1 N 0.7812(5) 0.6502(3) 0.4303(2) 0.0121(6) Uani 1 1 d . . . . .
H1A H 0.745105 0.609956 0.358641 0.014 Uiso 1 1 calc R U . . .
H1B H 0.949523 0.649597 0.442501 0.014 Uiso 1 1 calc R U . . .
H1C H 0.723885 0.747060 0.433322 0.014 Uiso 1 1 calc R U . . .
F3 F 0.7887(7) 0.5659(4) 0.0371(3) 0.0621(10) Uani 1 1 d . . . . .
F4 F 1.0714(7) 0.5825(4) 0.1806(3) 0.0654(11) Uani 1 1 d . . . . .
C1 C 0.3742(6) 0.5647(4) 0.5058(3) 0.0126(7) Uani 1 1 d . . . . .
C14 C 0.6099(6) 0.5429(4) 0.7408(3) 0.0157(8) Uani 1 1 d . . . . .
C2 C 0.6587(6) 0.5582(4) 0.5227(3) 0.0124(7) Uani 1 1 d . . . . .
H2 H 0.716650 0.450781 0.517713 0.015 Uiso 1 1 calc R U . . .
N11 N 0.3529(7) 0.3864(5) 0.9094(3) 0.0315(9) Uani 1 1 d . . . . .
H11 H 0.268949 0.335308 0.962039 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7360(6) 0.6257(4) 0.6430(3) 0.0162(8) Uani 1 1 d . . . . .
H3A H 0.919397 0.618263 0.653387 0.019 Uiso 1 1 calc R U . . .
H3B H 0.689506 0.734154 0.645438 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4142(7) 0.6100(5) 0.8016(3) 0.0202(8) Uani 1 1 d . . . . .
H13 H 0.367664 0.711624 0.784863 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6740(7) 0.3954(5) 0.7700(3) 0.0206(9) Uani 1 1 d . . . . .
H15 H 0.808715 0.347251 0.731580 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5451(8) 0.3189(5) 0.8536(3) 0.0229(9) Uani 1 1 d . . . . .
H16 H 0.590364 0.217839 0.872920 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2890(7) 0.5299(5) 0.8852(4) 0.0240(9) Uani 1 1 d . . . . .
H12 H 0.156249 0.576290 0.926273 0.029 Uiso 1 1 calc R U . . .
B1 B 0.8875(10) 0.4911(6) 0.1348(4) 0.0287(11) 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
O2 C1 1.248(4) . ?
O1 C1 1.255(4) . ?
F1 B1 1.385(6) . ?
F2 B1 1.375(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.491(4) . ?
F3 B1 1.394(6) . ?
F4 B1 1.372(6) . ?
C1 C2 1.534(5) . ?
C14 C3 1.503(5) . ?
C14 C13 1.396(5) . ?
C14 C15 1.387(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.548(5) . ?
N11 H11 0.8800 . ?
N11 C16 1.355(6) . ?
N11 C12 1.340(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.371(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.364(6) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
O2 C1 O1 125.9(3) . . ?
O2 C1 C2 117.3(3) . . ?
O1 C1 C2 116.7(3) . . ?
C13 C14 C3 120.7(3) . . ?
C15 C14 C3 121.6(3) . . ?
C15 C14 C13 117.6(4) . . ?
N1 C2 C1 109.7(3) . . ?
N1 C2 H2 109.7 . . ?
N1 C2 C3 107.6(3) . . ?
C1 C2 H2 109.7 . . ?
C1 C2 C3 110.5(3) . . ?
C3 C2 H2 109.7 . . ?
C16 N11 H11 119.6 . . ?
C12 N11 H11 119.6 . . ?
C12 N11 C16 120.8(4) . . ?
C14 C3 C2 110.8(3) . . ?
C14 C3 H3A 109.5 . . ?
C14 C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.8 . . ?
N11 C16 C15 120.4(4) . . ?
N11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
N11 C12 C13 120.4(4) . . ?
N11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
F1 B1 F3 109.5(4) . . ?
F2 B1 F1 110.3(4) . . ?
F2 B1 F3 108.0(4) . . ?
F4 B1 F1 109.1(4) . . ?
F4 B1 F2 113.0(5) . . ?
F4 B1 F3 106.8(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A F1 0.91 2.03 2.922(4) 165.4 . yes
N1 H1B O1 0.91 1.83 2.733(4) 170.4 1_655 yes
N1 H1C O2 0.91 1.89 2.741(4) 155.7 2_656 yes
C2 H2 O1 1.00 2.41 3.362(5) 158.5 2_646 yes
N11 H11 F2 0.88 2.24 2.994(5) 144.3 1_456 yes
N11 H11 F3 0.88 2.40 2.995(6) 125.3 2_646 yes
C3 H3A O2 0.99 2.58 3.318(4) 131.8 1_655 yes
C13 H13 F1 0.95 2.33 3.265(5) 167.5 2_656 yes
C16 H16 F4 0.95 2.26 2.958(5) 129.6 2_746 yes
C12 H12 F3 0.95 2.36 3.227(6) 152.2 1_456 yes

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
O2 C1 C2 N1 156.6(3) . . . . ?
O2 C1 C2 C3 -84.9(4) . . . . ?
O1 C1 C2 N1 -26.5(4) . . . . ?
O1 C1 C2 C3 92.0(4) . . . . ?
N1 C2 C3 C14 177.4(3) . . . . ?
C1 C2 C3 C14 57.7(4) . . . . ?
C14 C13 C12 N11 -0.1(6) . . . . ?
C14 C15 C16 N11 -0.1(6) . . . . ?
C3 C14 C13 C12 175.5(3) . . . . ?
C3 C14 C15 C16 -175.4(4) . . . . ?
C13 C14 C3 C2 -106.6(4) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C15 C14 C3 C2 70.1(4) . . . . ?
C15 C14 C13 C12 -1.3(5) . . . . ?
C16 N11 C12 C13 1.4(6) . . . . ?
C12 N11 C16 C15 -1.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
