 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H31 B F4 N2'
_chemical_formula_weight          374.27
 
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'
 '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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.5060(3)
_cell_length_b                    9.9913(5)
_cell_length_c                    13.4646(8)
_cell_angle_alpha                 71.383(2)
_cell_angle_beta                  87.972(3)
_cell_angle_gamma                 62.935(3)
_cell_volume                      1070.01(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6272
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.10
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.162
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9471
_exptl_absorpt_correction_T_max   0.9945
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             14127
_diffrn_reflns_av_R_equivalents   0.0649
_diffrn_reflns_av_sigmaI/netI     0.0616
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.19
_reflns_number_total              4658
_reflns_number_gt                 2398
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.1255P)²+0.1348P] 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
_refine_ls_extinction_coef        0.047(15)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4658
_refine_ls_number_parameters      266
_refine_ls_number_restraints      42
_refine_ls_R_factor_all           0.1401
_refine_ls_R_factor_gt            0.0730
_refine_ls_wR_factor_ref          0.2518
_refine_ls_wR_factor_gt           0.2087
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.040
_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
C1 C 0.8745(3) 0.4430(3) 0.37579(18) 0.0719(7) Uani 1 1 d . . .
H1 H 0.8264 0.3760 0.3825 0.086 Uiso 1 1 calc R . .
C2 C 0.9053(3) 0.6532(3) 0.35843(16) 0.0618(6) Uani 1 1 d . . .
C3 C 0.8864(4) 0.8018(3) 0.3513(2) 0.0817(8) Uani 1 1 d . . .
H3 H 0.7849 0.8893 0.3470 0.098 Uiso 1 1 calc R . .
C4 C 1.0244(5) 0.8139(5) 0.3509(2) 0.1041(10) Uani 1 1 d . . .
H4 H 1.0180 0.9130 0.3473 0.125 Uiso 1 1 calc R . .
C5 C 1.1718(5) 0.6887(5) 0.3554(3) 0.1062(10) Uani 1 1 d . . .
H5 H 1.2629 0.7050 0.3540 0.127 Uiso 1 1 calc R . .
C6 C 1.1915(3) 0.5426(4) 0.3620(2) 0.0895(9) Uani 1 1 d . . .
H6 H 1.2935 0.4564 0.3653 0.107 Uiso 1 1 calc R . .
C7 C 1.0524(3) 0.5266(3) 0.36359(17) 0.0651(6) Uani 1 1 d . . .
C8 C 0.6235(3) 0.6875(4) 0.3617(2) 0.0897(8) Uani 1 1 d . . .
H8A H 0.6001 0.7608 0.4021 0.108 Uiso 1 1 calc R . .
H8B H 0.5795 0.6135 0.3952 0.108 Uiso 1 1 calc R . .
C9 C 0.5437(3) 0.7830(4) 0.2497(2) 0.0946(9) Uani 1 1 d . . .
H9A H 0.4294 0.8517 0.2513 0.113 Uiso 1 1 calc R . .
H9B H 0.5908 0.8542 0.2165 0.113 Uiso 1 1 calc R . .
C10 C 0.5561(4) 0.6878(4) 0.1829(3) 0.1017(10) Uani 1 1 d . . .
H10A H 0.5090 0.6165 0.2162 0.122 Uiso 1 1 calc R . .
H10B H 0.6703 0.6191 0.1814 0.122 Uiso 1 1 calc R . .
C11 C 0.4751(4) 0.7844(4) 0.0693(3) 0.1149(11) Uani 1 1 d . . .
H11A H 0.3615 0.8545 0.0713 0.138 Uiso 1 1 calc R . .
H11B H 0.5234 0.8545 0.0361 0.138 Uiso 1 1 calc R . .
C12 C 0.4832(6) 0.6943(5) 0.0023(3) 0.1394(15) Uani 1 1 d . . .
H12A H 0.4300 0.6282 0.0335 0.167 Uiso 1 1 calc R . .
H12B H 0.5967 0.6203 0.0031 0.167 Uiso 1 1 calc R . .
C13 C 0.4099(7) 0.7902(6) -0.1113(3) 0.1653(19) Uani 1 1 d . . .
H13A H 0.2954 0.8579 -0.1141 0.248 Uiso 1 1 calc R . .
H13B H 0.4265 0.7175 -0.1502 0.248 Uiso 1 1 calc R . .
H13C H 0.4601 0.8577 -0.1434 0.248 Uiso 1 1 calc R . .
C14 C 1.1510(4) 0.2361(3) 0.3805(2) 0.0958(9) Uani 1 1 d . . .
H14A H 1.1114 0.1579 0.4127 0.115 Uiso 1 1 calc R . .
H14B H 1.2471 0.2058 0.4267 0.115 Uiso 1 1 calc R . .
C15 C 1.1952(4) 0.2291(4) 0.2736(3) 0.1077(11) Uani 1 1 d . . .
H15A H 1.2271 0.3130 0.2399 0.129 Uiso 1 1 calc R . .
H15B H 1.2887 0.1244 0.2828 0.129 Uiso 1 1 calc R . .
C16 C 1.0665(4) 0.2508(5) 0.2022(3) 0.1126(11) Uani 1 1 d . . .
H16A H 0.9757 0.3585 0.1895 0.135 Uiso 1 1 calc R . .
H16B H 1.0297 0.1715 0.2381 0.135 Uiso 1 1 calc R . .
C17 C 1.1121(5) 0.2337(5) 0.0970(3) 0.1261(13) Uani 1 1 d . . .
H17A H 1.1468 0.3146 0.0608 0.151 Uiso 1 1 calc R . .
H17B H 1.2050 0.1271 0.1101 0.151 Uiso 1 1 calc R . .
C18 C 0.9907(7) 0.2504(7) 0.0262(3) 0.1632(19) Uani 1 1 d . . .
H18A H 0.8977 0.3568 0.0136 0.196 Uiso 1 1 calc R . .
H18B H 0.9562 0.1694 0.0627 0.196 Uiso 1 1 calc R . .
C19 C 1.0323(8) 0.2346(8) -0.0766(4) 0.197(3) Uani 1 1 d . . .
H19A H 1.0663 0.3142 -0.1144 0.296 Uiso 1 1 calc R . .
H19B H 0.9391 0.2519 -0.1181 0.296 Uiso 1 1 calc R . .
H19C H 1.1193 0.1271 -0.0662 0.296 Uiso 1 1 calc R . .
B1 B 0.6537(4) 1.1980(4) 0.4291(3) 0.0836(9) Uani 1 1 d . . .
N1 N 0.7966(2) 0.5954(2) 0.36629(15) 0.0682(6) Uani 1 1 d . . .
N2 N 1.0280(2) 0.3964(2) 0.37467(15) 0.0691(6) Uani 1 1 d . . .
F1 F 0.6800(4) 1.1313(3) 0.5395(2) 0.1261(13) Uani 0.817(6) 1 d PU A 1
F2 F 0.7913(5) 1.1603(6) 0.3895(4) 0.149(2) Uani 0.817(6) 1 d PU A 1
F3 F 0.5719(8) 1.1416(8) 0.3931(4) 0.154(2) Uani 0.817(6) 1 d PU A 1
F1' F 0.573(3) 1.126(2) 0.451(3) 0.188(14) Uani 0.183(6) 1 d PU A 2
F2' F 0.8020(17) 1.133(2) 0.438(2) 0.191(15) Uani 0.183(6) 1 d PU A 2
F3' F 0.575(4) 1.314(3) 0.3287(15) 0.249(14) Uani 0.183(6) 1 d PU A 2
F4 F 0.5777(2) 1.3578(2) 0.4141(3) 0.1437(10) Uani 1 1 d U A .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N2 1.315(3) . ?
C1 N1 1.319(3) . ?
C1 H1 0.9500 . ?
C2 C7 1.379(3) . ?
C2 N1 1.382(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.358(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9500 . ?
C7 N2 1.385(3) . ?
C8 N1 1.466(3) . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.471(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.443(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.508(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N2 1.470(3) . ?
C14 C15 1.500(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.475(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.506(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.438(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.464(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
B1 F1' 1.245(18) . ?
B1 F2' 1.246(15) . ?
B1 F3 1.325(6) . ?
B1 F2 1.330(5) . ?
B1 F4 1.366(4) . ?
B1 F1 1.400(4) . ?
B1 F3' 1.418(17) . ?
F3' F4 1.36(2) . ?
 
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
N2 C1 N1 110.7(2) . . ?
N2 C1 H1 124.6 . . ?
N1 C1 H1 124.6 . . ?
C7 C2 N1 106.3(2) . . ?
C7 C2 C3 122.3(2) . . ?
N1 C2 C3 131.3(2) . . ?
C4 C3 C2 115.3(3) . . ?
C4 C3 H3 122.4 . . ?
C2 C3 H3 122.4 . . ?
C3 C4 C5 122.9(3) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.0(3) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
C2 C7 N2 106.9(2) . . ?
C2 C7 C6 121.2(3) . . ?
N2 C7 C6 131.9(2) . . ?
N1 C8 C9 111.7(2) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 115.1(3) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 115.3(3) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 116.5(3) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 C13 116.3(4) . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 111.9(2) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 114.2(3) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 114.9(3) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 116.4(4) . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C16 C17 H17B 108.2 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 C19 117.3(5) . . ?
C17 C18 H18A 108.0 . . ?
C19 C18 H18A 108.0 . . ?
C17 C18 H18B 108.0 . . ?
C19 C18 H18B 108.0 . . ?
H18A C18 H18B 107.2 . . ?
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 . . ?
F1' B1 F2' 125.4(16) . . ?
F2' B1 F3 121.9(11) . . ?
F1' B1 F2 130.6(14) . . ?
F3 B1 F2 110.0(5) . . ?
F1' B1 F4 117.2(12) . . ?
F2' B1 F4 116.0(10) . . ?
F3 B1 F4 116.6(4) . . ?
F2 B1 F4 109.5(3) . . ?
F1' B1 F1 75.6(16) . . ?
F2' B1 F1 83.3(14) . . ?
F3 B1 F1 108.2(4) . . ?
F2 B1 F1 110.6(4) . . ?
F4 B1 F1 101.5(3) . . ?
F1' B1 F3' 102.2(18) . . ?
F2' B1 F3' 115.0(18) . . ?
F3 B1 F3' 75.3(12) . . ?
F2 B1 F3' 88.7(13) . . ?
F4 B1 F3' 58.3(10) . . ?
F1 B1 F3' 156.8(11) . . ?
C1 N1 C2 108.28(19) . . ?
C1 N1 C8 125.4(2) . . ?
C2 N1 C8 126.3(2) . . ?
C1 N2 C7 107.85(19) . . ?
C1 N2 C14 126.1(2) . . ?
C7 N2 C14 126.0(2) . . ?
F4 F3' B1 58.9(8) . . ?
F3' F4 B1 62.7(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.977
_diffrn_reflns_theta_full              27.19
_diffrn_measured_fraction_theta_full   0.977
_refine_diff_density_max    0.265
_refine_diff_density_min   -0.234
_refine_diff_density_rms    0.039
