 
data_jm4554s 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H35 B F3 N' 
_chemical_formula_weight          393.33 
 
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            Monoclinic 
_symmetry_space_group_name_H-M    'P 21/m'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 '-x, -y, -z' 
 'x, -y-1/2, z' 
 
_cell_length_a                    8.0309(17) 
_cell_length_b                    14.995(3) 
_cell_length_c                    9.5461(19) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  106.162(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1104.2(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     203(2) 
_cell_measurement_reflns_used     1926 
_cell_measurement_theta_min       2.221
_cell_measurement_theta_max       30.35
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.183 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              424 
_exptl_absorpt_coefficient_mu     0.085 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9792 
_exptl_absorpt_correction_T_max   0.9883 
_exptl_absorpt_process_details    'Bruker Sadabs'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       203(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             10726 
_diffrn_reflns_av_R_equivalents   0.0593 
_diffrn_reflns_av_sigmaI/netI     0.0540 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.22 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              2639 
_reflns_number_gt                 1893 
_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 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 > 2sigma(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)+(0.0780P)²+0.0000P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2639 
_refine_ls_number_parameters      145 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0889 
_refine_ls_R_factor_gt            0.0647 
_refine_ls_wR_factor_ref          0.1880 
_refine_ls_wR_factor_gt           0.1772 
_refine_ls_goodness_of_fit_ref    1.363 
_refine_ls_restrained_S_all       1.363 
_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 
N N 0.7274(2) 0.2500 0.3129(2) 0.0263(5) Uani 1 2 d S . . 
B B 0.9960(3) 0.2500 0.5483(3) 0.0303(6) Uani 1 2 d S . . 
F1 F 1.10136(18) 0.2500 0.45697(17) 0.0460(5) Uani 1 2 d S . . 
C1 C 0.7854(3) 0.2500 0.4536(3) 0.0276(5) Uani 1 2 d S . . 
F2 F 1.02691(14) 0.17511(9) 0.63500(16) 0.0616(5) Uani 1 1 d . . . 
C2 C 0.6377(3) 0.2500 0.5235(3) 0.0337(6) Uani 1 2 d S . . 
C3 C 0.4756(4) 0.2500 0.3945(3) 0.0660(11) Uani 1 2 d S . . 
H3A H 0.4056 0.1970 0.3985 0.079 Uiso 0.50 1 calc PR . . 
H3B H 0.4056 0.3030 0.3985 0.079 Uiso 0.50 1 calc PR . . 
C4 C 0.5277(3) 0.2500 0.2540(3) 0.0304(5) Uani 1 2 d S . . 
C5 C 0.6457(3) 0.1679(2) 0.6172(4) 0.0841(11) Uani 1 1 d . . . 
H5A H 0.7582 0.1655 0.6910 0.101 Uiso 1 1 calc R . . 
H5B H 0.6347 0.1144 0.5563 0.101 Uiso 1 1 calc R . . 
C6 C 0.4992(4) 0.1691(4) 0.6929(5) 0.130(2) Uani 1 1 d . . . 
H6A H 0.3875 0.1641 0.6185 0.156 Uiso 1 1 calc R . . 
H6B H 0.5116 0.1169 0.7568 0.156 Uiso 1 1 calc R . . 
C7 C 0.4983(6) 0.2500 0.7797(6) 0.185(5) Uani 1 2 d S . . 
H7A H 0.3949 0.2500 0.8151 0.222 Uiso 1 2 calc SR . . 
H7B H 0.6005 0.2500 0.8647 0.222 Uiso 1 2 calc SR . . 
C8 C 0.4667(3) 0.16783(15) 0.1620(3) 0.0539(6) Uani 1 1 d . . . 
H8A H 0.5039 0.1149 0.2208 0.081 Uiso 1 1 calc R . . 
H8B H 0.5160 0.1675 0.0801 0.081 Uiso 1 1 calc R . . 
H8C H 0.3412 0.1684 0.1263 0.081 Uiso 1 1 calc R . . 
C9 C 0.8302(3) 0.2500 0.2090(3) 0.0274(5) Uani 1 2 d S . . 
C10 C 0.8755(2) 0.16824(12) 0.1587(2) 0.0324(4) Uani 1 1 d . . . 
C11 C 0.9540(2) 0.17083(14) 0.0458(2) 0.0405(5) Uani 1 1 d . . . 
H11 H 0.9835 0.1170 0.0084 0.049 Uiso 1 1 calc R . . 
C12 C 0.9894(3) 0.2500 -0.0123(3) 0.0425(7) Uani 1 2 d S . . 
H12 H 1.0377 0.2500 -0.0914 0.051 Uiso 1 2 calc SR . . 
C13 C 0.8608(3) 0.07869(12) 0.2292(2) 0.0418(5) Uani 1 1 d . . . 
H13 H 0.7939 0.0875 0.3010 0.050 Uiso 1 1 calc R . . 
C14 C 1.0430(3) 0.04514(14) 0.3116(3) 0.0539(6) Uani 1 1 d . . . 
H14A H 1.1100 0.0348 0.2428 0.081 Uiso 1 1 calc R . . 
H14B H 1.0331 -0.0101 0.3615 0.081 Uiso 1 1 calc R . . 
H14C H 1.1008 0.0896 0.3823 0.081 Uiso 1 1 calc R . . 
C15 C 0.7672(3) 0.00773(15) 0.1187(3) 0.0621(7) Uani 1 1 d . . . 
H15A H 0.6512 0.0283 0.0693 0.093 Uiso 1 1 calc R . . 
H15B H 0.7603 -0.0475 0.1695 0.093 Uiso 1 1 calc R . . 
H15C H 0.8313 -0.0023 0.0477 0.093 Uiso 1 1 calc R . . 
 
 
_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 
N C1 1.293(3) . ? 
N C9 1.456(3) . ? 
N C4 1.544(3) . ? 
B F1 1.373(3) . ? 
B F2 1.376(2) 4_565 ? 
B F2 1.376(2) . ? 
B C1 1.681(3) . ? 
C1 C2 1.514(3) . ? 
C2 C5 1.513(3) . ? 
C2 C5 1.513(3) 4_565 ? 
C2 C3 1.523(4) . ? 
C3 C4 1.512(4) . ? 
C3 H3A 0.9800 . ? 
C3 H3B 0.9800 . ? 
C4 C8 1.513(2) . ? 
C4 C8 1.513(2) 4_565 ? 
C5 C6 1.543(4) . ? 
C5 H5A 0.9800 . ? 
C5 H5B 0.9800 . ? 
C6 C7 1.470(6) . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C7 C6 1.470(6) 4_565 ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C8 H8C 0.9700 . ? 
C9 C10 1.401(2) . ? 
C9 C10 1.401(2) 4_565 ? 
C10 C11 1.393(3) . ? 
C10 C13 1.521(3) . ? 
C11 C12 1.373(2) . ? 
C11 H11 0.9400 . ? 
C12 C11 1.373(2) 4_565 ? 
C12 H12 0.9400 . ? 
C13 C14 1.540(3) . ? 
C13 C15 1.539(3) . ? 
C13 H13 0.9900 . ? 
C14 H14A 0.9700 . ? 
C14 H14B 0.9700 . ? 
C14 H14C 0.9700 . ? 
C15 H15A 0.9700 . ? 
C15 H15B 0.9700 . ? 
C15 H15C 0.9700 . ? 
 
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 
C1 N C9 126.76(18) . . ? 
C1 N C4 114.56(18) . . ? 
C9 N C4 118.68(18) . . ? 
F1 B F2 109.99(14) . 4_565 ? 
F1 B F2 109.99(14) . . ? 
F2 B F2 109.4(2) 4_565 . ? 
F1 B C1 111.4(2) . . ? 
F2 B C1 108.04(14) 4_565 . ? 
F2 B C1 108.03(14) . . ? 
N C1 C2 110.94(19) . . ? 
N C1 B 125.2(2) . . ? 
C2 C1 B 123.9(2) . . ? 
C5 C2 C5 109.0(3) . 4_565 ? 
C5 C2 C1 110.55(14) . . ? 
C5 C2 C1 110.55(14) 4_565 . ? 
C5 C2 C3 111.34(17) . . ? 
C5 C2 C3 111.34(17) 4_565 . ? 
C1 C2 C3 104.0(2) . . ? 
C4 C3 C2 109.4(2) . . ? 
C4 C3 H3A 109.8 . . ? 
C2 C3 H3A 109.8 . . ? 
C4 C3 H3B 109.8 . . ? 
C2 C3 H3B 109.8 . . ? 
H3A C3 H3B 108.3 . . ? 
C3 C4 C8 112.95(14) . . ? 
C3 C4 C8 112.95(14) . 4_565 ? 
C8 C4 C8 109.0(2) . 4_565 ? 
C3 C4 N 101.14(19) . . ? 
C8 C4 N 110.29(13) . . ? 
C8 C4 N 110.29(13) 4_565 . ? 
C2 C5 C6 110.8(2) . . ? 
C2 C5 H5A 109.5 . . ? 
C6 C5 H5A 109.5 . . ? 
C2 C5 H5B 109.5 . . ? 
C6 C5 H5B 109.5 . . ? 
H5A C5 H5B 108.1 . . ? 
C7 C6 C5 113.5(4) . . ? 
C7 C6 H6A 108.9 . . ? 
C5 C6 H6A 108.9 . . ? 
C7 C6 H6B 108.9 . . ? 
C5 C6 H6B 108.9 . . ? 
H6A C6 H6B 107.7 . . ? 
C6 C7 C6 111.2(4) 4_565 . ? 
C6 C7 H7A 109.4 4_565 . ? 
C6 C7 H7A 109.4 . . ? 
C6 C7 H7B 109.4 4_565 . ? 
C6 C7 H7B 109.4 . . ? 
H7A C7 H7B 108.0 . . ? 
C4 C8 H8A 109.5 . . ? 
C4 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
C4 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 109.5 . . ? 
C10 C9 C10 122.1(2) . 4_565 ? 
C10 C9 N 118.94(11) . . ? 
C10 C9 N 118.94(11) 4_565 . ? 
C11 C10 C9 117.23(17) . . ? 
C11 C10 C13 118.31(16) . . ? 
C9 C10 C13 124.17(16) . . ? 
C12 C11 C10 121.75(18) . . ? 
C12 C11 H11 119.1 . . ? 
C10 C11 H11 119.1 . . ? 
C11 C12 C11 119.6(2) . 4_565 ? 
C11 C12 H12 120.2 . . ? 
C11 C12 H12 120.2 4_565 . ? 
C10 C13 C14 109.55(16) . . ? 
C10 C13 C15 113.00(18) . . ? 
C14 C13 C15 109.72(17) . . ? 
C10 C13 H13 108.1 . . ? 
C14 C13 H13 108.1 . . ? 
C15 C13 H13 108.1 . . ? 
C13 C14 H14A 109.5 . . ? 
C13 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C13 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C13 C15 H15A 109.5 . . ? 
C13 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C13 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.452 
_refine_diff_density_min   -0.296 
_refine_diff_density_rms    0.053 
