# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_N-IPBAT-100K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Tetrafluoroborate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, B F4'
_chemical_formula_sum            'C10 H16 B F4 N'
_chemical_formula_weight         237.05

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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                   19.5994(6)
_cell_length_b                   7.7561(2)
_cell_length_c                   32.5648(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.614(3)
_cell_angle_gamma                90.00
_cell_volume                     4926.6(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16451
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5030
_reflns_number_gt                3910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+13.4130P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5024
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_ref         0.2236
_refine_ls_wR_factor_gt          0.2094
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26882(9) 0.6780(3) 0.19923(6) 0.0210(4) Uani 1 1 d . . .
H1A H 0.2681 0.5709 0.2114 0.025 Uiso 1 1 calc R . .
H1B H 0.2564 0.7574 0.2181 0.025 Uiso 1 1 calc R . .
F3 F 0.23277(9) 0.8240(2) 0.27915(5) 0.0416(4) Uani 1 1 d . . .
F1 F 0.15603(9) 0.6557(3) 0.30882(7) 0.0557(5) Uani 1 1 d . . .
C7 C 0.21625(12) 0.6809(4) 0.16240(8) 0.0343(6) Uani 1 1 d . . .
H7A H 0.2261 0.5871 0.1432 0.041 Uiso 1 1 calc R . .
H7B H 0.2193 0.7919 0.1477 0.041 Uiso 1 1 calc R . .
C6 C 0.14464(12) 0.6589(4) 0.17494(7) 0.0359(7) Uani 1 1 d . . .
C8 C 0.34156(12) 0.7163(3) 0.18987(8) 0.0288(5) Uani 1 1 d . . .
H9 H 0.3421 0.8342 0.1775 0.035 Uiso 1 1 calc R . .
B1 B 0.22412(15) 0.6842(4) 0.30558(9) 0.0283(6) Uani 1 1 d . . .
C10 C 0.36616(15) 0.5912(4) 0.15948(10) 0.0449(7) Uani 1 1 d . . .
H10A H 0.4136 0.6185 0.1548 0.067 Uiso 1 1 calc R . .
H10B H 0.3370 0.5995 0.1333 0.067 Uiso 1 1 calc R . .
H10C H 0.3639 0.4738 0.1704 0.067 Uiso 1 1 calc R . .
F2 F 0.25614(12) 0.7225(3) 0.34365(6) 0.0725(7) Uani 1 1 d . . .
C9 C 0.38605(14) 0.7198(5) 0.23037(9) 0.0493(8) Uani 1 1 d . . .
H9A H 0.3677 0.8039 0.2489 0.074 Uiso 1 1 calc R . .
H9B H 0.4329 0.7524 0.2255 0.074 Uiso 1 1 calc R . .
H9C H 0.3865 0.6052 0.2431 0.074 Uiso 1 1 calc R . .
C1 C 0.11164(15) 0.5006(5) 0.16987(10) 0.0457(8) Uani 1 1 d . . .
H1 H 0.1348 0.4052 0.1593 0.055 Uiso 1 1 calc R . .
C3 C 0.01137(15) 0.6188(6) 0.19561(9) 0.0572(11) Uani 1 1 d . . .
H3 H -0.0340 0.6051 0.2030 0.069 Uiso 1 1 calc R . .
C5 C 0.11038(14) 0.7976(5) 0.19006(9) 0.0466(8) Uani 1 1 d . . .
H5 H 0.1323 0.9066 0.1934 0.056 Uiso 1 1 calc R . .
C4 C 0.04332(16) 0.7766(6) 0.20043(10) 0.0588(10) Uani 1 1 d . . .
H4 H 0.0197 0.8716 0.2108 0.071 Uiso 1 1 calc R . .
C2 C 0.04475(16) 0.4813(6) 0.18017(10) 0.0562(10) Uani 1 1 d . . .
H2 H 0.0223 0.3730 0.1765 0.067 Uiso 1 1 calc R . .
F8 F 0.49333(9) 0.61571(19) 0.03148(5) 0.0377(4) Uani 1 1 d . . .
N2 N 0.48238(9) 1.2582(2) 0.05117(6) 0.0214(4) Uani 1 1 d . . .
H2A H 0.4859 1.1475 0.0414 0.026 Uiso 1 1 calc R . .
H2B H 0.4923 1.3323 0.0305 0.026 Uiso 1 1 calc R . .
C18 C 0.40907(12) 1.2889(3) 0.06049(8) 0.0280(5) Uani 1 1 d . . .
H18 H 0.4047 1.4116 0.0693 0.034 Uiso 1 1 calc R . .
C17 C 0.53497(13) 1.2824(4) 0.08744(7) 0.0324(6) Uani 1 1 d . . .
H17A H 0.5260 1.3924 0.1014 0.039 Uiso 1 1 calc R . .
H17B H 0.5309 1.1877 0.1074 0.039 Uiso 1 1 calc R . .
F7 F 0.48413(15) 0.9027(2) 0.03424(8) 0.0829(8) Uani 1 1 d . . .
F5 F 0.40832(13) 0.7391(3) 0.06341(10) 0.0918(9) Uani 1 1 d . . .
C16 C 0.60629(13) 1.2847(5) 0.07455(8) 0.0457(8) Uani 1 1 d . . .
C19 C 0.38962(13) 1.1744(4) 0.09470(8) 0.0371(6) Uani 1 1 d . . .
H19A H 0.3424 1.1996 0.1003 0.056 Uiso 1 1 calc R . .
H19B H 0.4207 1.1956 0.1196 0.056 Uiso 1 1 calc R . .
H19C H 0.3931 1.0534 0.0865 0.056 Uiso 1 1 calc R . .
B2 B 0.47527(19) 0.7530(4) 0.05616(10) 0.0383(7) Uani 1 1 d . . .
C15 C 0.63668(16) 1.1378(7) 0.06205(10) 0.0733(14) Uani 1 1 d . . .
H15 H 0.6122 1.0320 0.0606 0.088 Uiso 1 1 calc R . .
C14 C 0.7040(2) 1.1442(11) 0.05143(12) 0.122(3) Uani 1 1 d . . .
H14 H 0.7253 1.0430 0.0423 0.146 Uiso 1 1 calc R . .
C20 C 0.36352(14) 1.2622(5) 0.02043(9) 0.0494(9) Uani 1 1 d . . .
H20A H 0.3773 1.3423 -0.0005 0.074 Uiso 1 1 calc R . .
H20B H 0.3156 1.2838 0.0251 0.074 Uiso 1 1 calc R . .
H20C H 0.3683 1.1434 0.0109 0.074 Uiso 1 1 calc R . .
C11 C 0.64302(18) 1.4397(6) 0.07714(12) 0.0757(14) Uani 1 1 d . . .
H11 H 0.6220 1.5425 0.0856 0.091 Uiso 1 1 calc R . .
C12 C 0.7096(2) 1.4424(11) 0.06743(17) 0.122(3) Uani 1 1 d . . .
H12 H 0.7349 1.5471 0.0700 0.146 Uiso 1 1 calc R . .
F6 F 0.5133(2) 0.7520(5) 0.09194(8) 0.1286(14) Uani 1 1 d . . .
C13 C 0.7398(2) 1.2991(14) 0.05435(12) 0.131(4) Uani 1 1 d . . .
H13 H 0.7856 1.3039 0.0471 0.157 Uiso 1 1 calc R . .
F4 F 0.25287(10) 0.5418(2) 0.28822(7) 0.0584(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0213(9) 0.0210(10) 0.0213(9) 0.0005(7) 0.0054(7) 0.0010(7)
F3 0.0663(11) 0.0216(8) 0.0400(9) 0.0016(6) 0.0202(8) 0.0010(7)
F1 0.0369(9) 0.0553(12) 0.0788(14) -0.0075(10) 0.0247(9) -0.0074(8)
C7 0.0243(12) 0.0566(18) 0.0221(12) 0.0051(12) 0.0029(9) 0.0020(11)
C6 0.0231(12) 0.0640(19) 0.0204(12) 0.0084(12) 0.0006(9) 0.0035(12)
C8 0.0238(12) 0.0297(13) 0.0340(13) 0.0004(10) 0.0091(10) -0.0030(10)
B1 0.0344(15) 0.0214(14) 0.0308(14) 0.0003(11) 0.0122(11) -0.0007(11)
C10 0.0344(14) 0.0478(18) 0.0556(18) -0.0099(15) 0.0202(13) -0.0036(13)
F2 0.0776(15) 0.1012(18) 0.0369(10) 0.0080(11) -0.0046(10) -0.0244(13)
C9 0.0249(13) 0.082(2) 0.0407(16) -0.0067(16) 0.0036(11) -0.0107(15)
C1 0.0332(14) 0.058(2) 0.0455(16) 0.0203(15) 0.0007(12) 0.0011(14)
C3 0.0258(14) 0.117(3) 0.0288(14) 0.0117(18) 0.0032(11) -0.0037(18)
C5 0.0290(14) 0.078(2) 0.0326(14) -0.0144(15) 0.0003(11) 0.0013(14)
C4 0.0337(15) 0.109(3) 0.0336(16) -0.0154(18) 0.0042(12) 0.0134(19)
C2 0.0342(15) 0.081(3) 0.0530(19) 0.0292(19) 0.0002(14) -0.0105(16)
F8 0.0621(10) 0.0219(8) 0.0315(8) -0.0011(6) 0.0156(7) 0.0017(7)
N2 0.0228(10) 0.0191(10) 0.0225(9) 0.0015(7) 0.0029(7) -0.0014(7)
C18 0.0223(11) 0.0296(13) 0.0329(13) 0.0005(10) 0.0060(10) 0.0044(10)
C17 0.0285(13) 0.0456(16) 0.0227(12) 0.0023(11) -0.0001(9) -0.0053(11)
F7 0.147(2) 0.0192(9) 0.0946(17) 0.0017(10) 0.0728(16) -0.0031(11)
F5 0.0810(17) 0.0637(16) 0.142(2) -0.0132(15) 0.0675(17) 0.0002(12)
C16 0.0241(13) 0.093(3) 0.0189(12) 0.0117(14) -0.0019(10) -0.0140(15)
C19 0.0303(13) 0.0447(17) 0.0379(14) 0.0029(12) 0.0111(11) -0.0010(12)
B2 0.060(2) 0.0227(15) 0.0342(16) -0.0041(12) 0.0161(14) -0.0012(14)
C15 0.0292(15) 0.149(4) 0.0411(18) -0.041(2) 0.0004(13) 0.003(2)
C14 0.033(2) 0.288(9) 0.044(2) -0.061(4) -0.0011(16) 0.019(3)
C20 0.0261(13) 0.085(3) 0.0363(15) 0.0097(16) 0.0001(11) 0.0042(14)
C11 0.0439(19) 0.108(3) 0.070(2) 0.055(2) -0.0242(17) -0.034(2)
C12 0.045(2) 0.229(8) 0.085(4) 0.102(5) -0.024(2) -0.065(4)
F6 0.186(3) 0.135(3) 0.0545(15) -0.0450(17) -0.0372(18) 0.045(2)
C13 0.0247(19) 0.337(11) 0.0298(19) 0.036(4) -0.0007(15) -0.028(4)
F4 0.0715(13) 0.0232(9) 0.0882(15) 0.0039(9) 0.0471(11) 0.0083(8)

_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
N1 C7 1.503(3) . ?
N1 C8 1.516(3) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
F3 B1 1.405(3) . ?
F1 B1 1.367(3) . ?
C7 C6 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C5 1.384(4) . ?
C6 C1 1.390(5) . ?
C8 C10 1.499(4) . ?
C8 C9 1.508(4) . ?
C8 H9 1.0000 . ?
B1 F2 1.367(3) . ?
B1 F4 1.385(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 C2 1.393(4) . ?
C1 H1 0.9500 . ?
C3 C2 1.372(6) . ?
C3 C4 1.377(6) . ?
C3 H3 0.9500 . ?
C5 C4 1.398(4) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
F8 B2 1.400(3) . ?
N2 C17 1.502(3) . ?
N2 C18 1.516(3) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C18 C19 1.502(4) . ?
C18 C20 1.521(4) . ?
C18 H18 1.0000 . ?
C17 C16 1.498(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
F7 B2 1.383(4) . ?
F5 B2 1.360(4) . ?
C16 C15 1.366(6) . ?
C16 C11 1.400(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
B2 F6 1.320(4) . ?
C15 C14 1.398(5) . ?
C15 H15 0.9500 . ?
C14 C13 1.389(11) . ?
C14 H14 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C11 C12 1.373(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.348(11) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 114.91(18) . . ?
C7 N1 H1A 108.5 . . ?
C8 N1 H1A 108.5 . . ?
C7 N1 H1B 108.5 . . ?
C8 N1 H1B 108.5 . . ?
H1A N1 H1B 107.5 . . ?
N1 C7 C6 111.43(19) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 120.1(3) . . ?
C10 C8 C9 113.1(2) . . ?
C10 C8 N1 112.0(2) . . ?
C9 C8 N1 107.6(2) . . ?
C10 C8 H9 108.0 . . ?
C9 C8 H9 108.0 . . ?
N1 C8 H9 108.0 . . ?
F2 B1 F1 109.3(2) . . ?
F2 B1 F4 112.0(3) . . ?
F1 B1 F4 110.0(2) . . ?
F2 B1 F3 108.4(2) . . ?
F1 B1 F3 110.5(2) . . ?
F4 B1 F3 106.7(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C17 N2 C18 114.44(18) . . ?
C17 N2 H2A 108.7 . . ?
C18 N2 H2A 108.7 . . ?
C17 N2 H2B 108.7 . . ?
C18 N2 H2B 108.7 . . ?
H2A N2 H2B 107.6 . . ?
C19 C18 N2 111.7(2) . . ?
C19 C18 C20 112.7(2) . . ?
N2 C18 C20 107.2(2) . . ?
C19 C18 H18 108.4 . . ?
N2 C18 H18 108.4 . . ?
C20 C18 H18 108.4 . . ?
C16 C17 N2 111.6(2) . . ?
C16 C17 H17A 109.3 . . ?
N2 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
N2 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C15 C16 C11 119.8(3) . . ?
C15 C16 C17 121.3(3) . . ?
C11 C16 C17 118.8(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F6 B2 F5 108.5(3) . . ?
F6 B2 F7 111.8(3) . . ?
F5 B2 F7 109.2(3) . . ?
F6 B2 F8 110.5(3) . . ?
F5 B2 F8 110.0(3) . . ?
F7 B2 F8 106.9(2) . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C11 C16 119.6(6) . . ?
C12 C11 H11 120.2 . . ?
C16 C11 H11 120.2 . . ?
C13 C12 C11 121.1(6) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?

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
C8 N1 C7 C6 -174.4(2) . . . . ?
N1 C7 C6 C5 80.1(3) . . . . ?
N1 C7 C6 C1 -102.4(3) . . . . ?
C7 N1 C8 C10 -58.8(3) . . . . ?
C7 N1 C8 C9 176.2(2) . . . . ?
C5 C6 C1 C2 -0.4(4) . . . . ?
C7 C6 C1 C2 -177.9(2) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
C7 C6 C5 C4 178.1(2) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C4 C3 C2 C1 0.9(5) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C17 N2 C18 C19 -57.2(3) . . . . ?
C17 N2 C18 C20 178.9(2) . . . . ?
C18 N2 C17 C16 -168.8(2) . . . . ?
N2 C17 C16 C15 -72.0(3) . . . . ?
N2 C17 C16 C11 110.6(3) . . . . ?
C11 C16 C15 C14 -0.8(5) . . . . ?
C17 C16 C15 C14 -178.1(3) . . . . ?
C16 C15 C14 C13 1.1(6) . . . . ?
C15 C16 C11 C12 -0.6(5) . . . . ?
C17 C16 C11 C12 176.8(3) . . . . ?
C16 C11 C12 C13 1.8(6) . . . . ?
C11 C12 C13 C14 -1.5(7) . . . . ?
C15 C14 C13 C12 0.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 950201'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_N-IPBAT-293K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'N-Isopropylbenzylammonium Tetrafluoroborate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 N, B F4'
_chemical_formula_sum            'C10 H18 B F4 N'
_chemical_formula_weight         239.06

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'
N N 0.0061 0.0033 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.493(4)
_cell_length_b                   7.7954(16)
_cell_length_c                   10.016(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.35(3)
_cell_angle_gamma                90.00
_cell_volume                     1258.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3693
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.74
_reflns_number_total             1547
_reflns_number_gt                819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1823P)^2^+1.3801P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1598
_refine_ls_number_parameters     92
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0939
_refine_ls_wR_factor_ref         0.3572
_refine_ls_wR_factor_gt          0.3018
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2822(2) 0.0000 0.8616(3) 0.0514(9) Uani 1 2 d S . .
H1A H 0.2741 0.0950 0.9071 0.062 Uiso 0.50 1 calc PR . .
H1B H 0.2741 -0.0950 0.9071 0.062 Uiso 0.50 1 calc PR . .
C1 C 0.4295(3) 0.0000 1.0650(6) 0.093(2) Uani 1 2 d SD . .
C5 C 0.3698(3) 0.0000 0.8965(5) 0.0808(17) Uani 1 2 d S . .
H5A H 0.3799 0.1026 0.8498 0.097 Uiso 0.50 1 calc PR . .
H5B H 0.3799 -0.1026 0.8498 0.097 Uiso 0.50 1 calc PR . .
F2 F 0.2294(2) 0.1384(3) 1.0843(3) 0.1143(13) Uani 1 1 d . . .
C6 C 0.2173(3) 0.0000 0.6973(6) 0.093(2) Uani 1 2 d S . .
B1 B 0.2237(4) 0.0000 1.1609(7) 0.0709(16) Uani 1 2 d S . .
C8 C 0.1339(3) 0.0000 0.6858(7) 0.098(2) Uani 1 2 d S . .
H8A H 0.1340 -0.0788 0.7621 0.146 Uiso 0.50 1 calc PR . .
H8B H 0.0922 -0.0373 0.5830 0.146 Uiso 0.50 1 calc PR . .
H8C H 0.1206 0.1161 0.7046 0.146 Uiso 0.50 1 calc PR . .
F3 F 0.2853(4) 0.0000 1.3056(5) 0.168(2) Uani 1 2 d S . .
C2 C 0.4581(3) 0.1517(9) 1.1404(6) 0.158(3) Uani 1 1 d D . .
H2 H 0.4384 0.2569 1.0868 0.189 Uiso 1 1 calc R . .
C7 C 0.2312(5) 0.0791(13) 0.5903(8) 0.092(3) Uani 0.50 1 d P . .
F1 F 0.1558(4) 0.0000 1.1674(8) 0.186(3) Uani 1 2 d S . .
C4 C 0.5420(6) 0.0000 1.3678(10) 0.231(11) Uani 1 2 d SD . .
H4 H 0.5803 0.0000 1.4746 0.277 Uiso 1 2 calc SR . .
C3 C 0.5160(4) 0.1528(14) 1.2953(8) 0.249(8) Uani 1 1 d D . .
H3 H 0.5368 0.2577 1.3489 0.299 Uiso 1 1 calc R . .
H7C H 0.1868 0.0655 0.4978 0.299 Uiso 0.50 1 d PR . .
H7A H 0.2757 0.0319 0.5922 0.299 Uiso 0.50 1 d PR . .
H7B H 0.2398 0.1911 0.6125 0.299 Uiso 1 1 d R . .
H6A H 0.2111 -0.1081 0.6668 0.299 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.055(2) 0.058(2) 0.0395(18) 0.000 0.0213(15) 0.000
C1 0.047(3) 0.180(7) 0.055(3) 0.000 0.028(2) 0.000
C5 0.055(3) 0.138(5) 0.052(3) 0.000 0.029(2) 0.000
F2 0.195(3) 0.0610(15) 0.116(2) 0.0096(12) 0.098(2) 0.0030(14)
C6 0.064(3) 0.160(6) 0.042(3) 0.000 0.015(2) 0.000
B1 0.107(5) 0.055(3) 0.062(3) 0.000 0.050(3) 0.000
C8 0.056(3) 0.153(6) 0.063(3) 0.000 0.014(2) 0.000
F3 0.207(6) 0.173(5) 0.074(3) 0.000 0.030(3) 0.000
C2 0.075(3) 0.253(8) 0.102(4) -0.083(5) 0.010(3) 0.041(4)
C7 0.094(5) 0.129(7) 0.047(4) 0.012(4) 0.029(4) -0.002(4)
F1 0.188(6) 0.210(7) 0.245(7) 0.000 0.172(6) 0.000
C4 0.066(5) 0.57(3) 0.062(5) 0.000 0.037(4) 0.000
C3 0.087(4) 0.49(2) 0.124(6) -0.156(9) 0.014(4) 0.057(7)

_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
N1 C5 1.479(6) . ?
N1 C6 1.487(6) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C1 C2 1.363(6) . ?
C1 C2 1.363(6) 6 ?
C1 C5 1.497(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
F2 B1 1.358(4) . ?
C6 C7 1.366(9) 6 ?
C6 C7 1.366(9) . ?
C6 C8 1.489(8) . ?
C6 H6A 0.8842 . ?
B1 F1 1.289(8) . ?
B1 F3 1.334(8) . ?
B1 F2 1.358(4) 6 ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9500 . ?
C7 C7 1.23(2) 6 ?
C7 H7C 0.8932 . ?
C7 H7A 0.8925 . ?
C7 H7B 0.8961 . ?
C4 C3 1.355(10) 6 ?
C4 C3 1.355(10) . ?
C4 H4 0.9500 . ?
C3 H3 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
C5 N1 C6 117.3(4) . . ?
C5 N1 H1A 108.0 . . ?
C6 N1 H1A 108.0 . . ?
C5 N1 H1B 108.0 . . ?
C6 N1 H1B 108.0 . . ?
H1A N1 H1B 107.2 . . ?
C2 C1 C2 120.4(7) . 6 ?
C2 C1 C5 119.8(3) . . ?
C2 C1 C5 119.8(3) 6 . ?
N1 C5 C1 112.6(4) . . ?
N1 C5 H5A 109.1 . . ?
C1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C1 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C7 53.7(9) 6 . ?
C7 C6 N1 120.5(5) 6 . ?
C7 C6 N1 120.5(5) . . ?
C7 C6 C8 121.7(5) 6 . ?
C7 C6 C8 121.7(5) . . ?
N1 C6 C8 109.3(4) . . ?
C7 C6 H6A 48.7 6 . ?
C7 C6 H6A 101.6 . . ?
N1 C6 H6A 106.3 . . ?
C8 C6 H6A 91.1 . . ?
F1 B1 F3 106.2(6) . . ?
F1 B1 F2 112.1(4) . 6 ?
F3 B1 F2 110.6(4) . 6 ?
F1 B1 F2 112.1(4) . . ?
F3 B1 F2 110.6(4) . . ?
F2 B1 F2 105.3(4) 6 . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C2 C3 120.2(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C7 C7 C6 63.2(4) 6 . ?
C7 C7 H7C 83.2 6 . ?
C6 C7 H7C 109.2 . . ?
C7 C7 H7A 65.7 6 . ?
C6 C7 H7A 108.8 . . ?
H7C C7 H7A 110.0 . . ?
C7 C7 H7B 167.0 6 . ?
C6 C7 H7B 108.9 . . ?
H7C C7 H7B 109.6 . . ?
H7A C7 H7B 110.3 . . ?
C3 C4 C3 123.1(9) 6 . ?
C3 C4 H4 118.4 6 . ?
C3 C4 H4 118.4 . . ?
C4 C3 C2 118.1(8) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?

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
C6 N1 C5 C1 180.000(2) . . . . ?
C2 C1 C5 N1 -91.7(4) . . . . ?
C2 C1 C5 N1 91.7(4) 6 . . . ?
C5 N1 C6 C7 31.6(6) . . . 6 ?
C5 N1 C6 C7 -31.6(5) . . . . ?
C5 N1 C6 C8 180.000(2) . . . . ?
C2 C1 C2 C3 -0.8(10) 6 . . . ?
C5 C1 C2 C3 -177.4(5) . . . . ?
N1 C6 C7 C7 107.4(5) . . . 6 ?
C8 C6 C7 C7 -108.2(4) . . . 6 ?
C3 C4 C3 C2 2.0(15) 6 . . . ?
C1 C2 C3 C4 -0.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.74
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.060

# start Validation Reply Form
_vrf_PLAT241_N-IPBAT-293K        
;
PROBLEM: Check High      Ueq as Compared to Neighbors for         C3      
RESPONSE: Because the benzene rings in the N-IPBA is slightly disordered, the C2 and C3 atoms have higher Ueq than C1 and C4 atoms. 
;
_vrf_PLAT410_N-IPBAT-293K        
;
PROBLEM: Short Intra H...H Contact  H6A    ..  H7A     ..       1.79 Ang. 
RESPONSE: This problem may be due to the disordered nature of the methyl group (C7H7AH7BH7C).
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 950202'