 
data_03src661
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C21 H35 N2, B F4'
_chemical_formula_sum
 'C21 H35 B F4 N2'
_chemical_formula_weight          402.32
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   -P1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.2690(3)
_cell_length_b                    9.9893(3)
_cell_length_c                    14.5557(6)
_cell_angle_alpha                 106.773(2)
_cell_angle_beta                  92.343(2)
_cell_angle_gamma                 116.871(2)
_cell_volume                      1127.66(7)
_cell_formula_units_Z             1
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     30288
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     0.592
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              216
_exptl_absorpt_coefficient_mu     0.046
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9820
_exptl_absorpt_correction_T_max   0.9982
_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             20016
_diffrn_reflns_av_R_equivalents   0.1675
_diffrn_reflns_av_sigmaI/netI     0.1063
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5113
_reflns_number_gt                 3603
_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     'PLATON (Watkin, Pearce 1995)'
_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)+(0.1035P)²+0.1029P] 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        0.12(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5113
_refine_ls_number_parameters      256
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1024
_refine_ls_R_factor_gt            0.0742
_refine_ls_wR_factor_ref          0.2168
_refine_ls_wR_factor_gt           0.1946
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_restrained_S_all       1.034
_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 0.6829(3) 0.0515(2) 0.38230(15) 0.0266(5) Uani 0.50 1 d P . .
H1 H 0.7971 0.1179 0.3861 0.032 Uiso 0.50 1 calc PR . .
C2 C 0.4181(3) -0.0308(2) 0.37705(14) 0.0244(5) Uani 0.50 1 d P . .
C3 C 0.2626(3) -0.0441(3) 0.37864(15) 0.0283(5) Uani 0.50 1 d P . .
H3 H 0.2438 0.0433 0.3834 0.034 Uiso 0.50 1 calc PR . .
C4 C 0.1367(3) -0.1920(3) 0.37293(16) 0.0330(5) Uani 0.50 1 d P . .
H4 H 0.0283 -0.2064 0.3737 0.040 Uiso 0.50 1 calc PR . .
C5 C 0.1642(3) -0.3212(3) 0.36600(16) 0.0330(5) Uani 0.50 1 d P . .
H5 H 0.0742 -0.4201 0.3631 0.040 Uiso 0.50 1 calc PR . .
C6 C 0.3185(3) -0.3085(3) 0.36325(15) 0.0297(5) Uani 0.50 1 d P . .
H6 H 0.3370 -0.3963 0.3577 0.036 Uiso 0.50 1 calc PR . .
C7 C 0.4455(3) -0.1594(2) 0.36916(14) 0.0241(5) Uani 0.50 1 d P . .
C8 C 0.6009(3) 0.2607(2) 0.39228(16) 0.0284(5) Uani 0.50 1 d P . .
H8A H 0.7200 0.3379 0.4169 0.034 Uiso 0.50 1 calc PR . .
H8B H 0.5396 0.2939 0.4397 0.034 Uiso 0.50 1 calc PR . .
C9 C 0.5464(3) 0.2639(3) 0.29343(16) 0.0304(5) Uani 0.50 1 d P . .
H9A H 0.5456 0.3658 0.3032 0.036 Uiso 0.50 1 calc PR . .
H9B H 0.4321 0.1758 0.2648 0.036 Uiso 0.50 1 calc PR . .
C10 C 0.6571(3) 0.2473(3) 0.22128(16) 0.0322(5) Uani 0.50 1 d P . .
H10A H 0.7702 0.3384 0.2484 0.039 Uiso 0.50 1 calc PR . .
H10B H 0.6622 0.1480 0.2139 0.039 Uiso 0.50 1 calc PR . .
C11 C 0.5976(3) 0.2427(3) 0.12091(16) 0.0312(5) Uani 0.50 1 d P . .
H11A H 0.5832 0.3375 0.1289 0.037 Uiso 0.50 1 calc PR . .
H11B H 0.4885 0.1464 0.0913 0.037 Uiso 0.50 1 calc PR . .
C12 C 0.7159(3) 0.2403(3) 0.05140(16) 0.0349(5) Uani 0.50 1 d P . .
H12A H 0.8253 0.3361 0.0816 0.042 Uiso 0.50 1 calc PR . .
H12B H 0.7296 0.1451 0.0434 0.042 Uiso 0.50 1 calc PR . .
C13 C 0.6600(3) 0.2370(3) -0.04928(16) 0.0358(5) Uani 0.50 1 d P . .
H13A H 0.5541 0.1378 -0.0816 0.043 Uiso 0.50 1 calc PR . .
H13B H 0.6403 0.3288 -0.0415 0.043 Uiso 0.50 1 calc PR . .
C14 C 0.7850(4) 0.2444(4) -0.11426(19) 0.0495(7) Uani 0.50 1 d P . .
H14A H 0.8923 0.3382 -0.0806 0.074 Uiso 0.50 1 calc PR . .
H14B H 0.7482 0.2523 -0.1756 0.074 Uiso 0.50 1 calc PR . .
H14C H 0.7954 0.1474 -0.1286 0.074 Uiso 0.50 1 calc PR . .
C15 C 0.7013(3) -0.1955(3) 0.36842(16) 0.0297(5) Uani 0.50 1 d P . .
H15A H 0.6563 -0.2658 0.4077 0.036 Uiso 0.50 1 calc PR . .
H15B H 0.8199 -0.1217 0.3975 0.036 Uiso 0.50 1 calc PR . .
C16 C 0.6837(3) -0.2973(3) 0.26371(16) 0.0318(5) Uani 0.50 1 d P . .
H16A H 0.5648 -0.3701 0.2351 0.038 Uiso 0.50 1 calc PR . .
H16B H 0.7357 -0.3643 0.2654 0.038 Uiso 0.50 1 calc PR . .
C17 C 0.7599(3) -0.2031(3) 0.19670(17) 0.0345(5) Uani 0.50 1 d P . .
H17A H 0.8781 -0.1274 0.2258 0.041 Uiso 0.50 1 calc PR . .
H17B H 0.7047 -0.1399 0.1919 0.041 Uiso 0.50 1 calc PR . .
C18 C 0.7447(3) -0.3109(3) 0.09417(17) 0.0353(6) Uani 0.50 1 d P . .
H18A H 0.8027 -0.3716 0.0993 0.042 Uiso 0.50 1 calc PR . .
H18B H 0.6266 -0.3891 0.0665 0.042 Uiso 0.50 1 calc PR . .
C19 C 0.8142(3) -0.2221(3) 0.02406(17) 0.0355(5) Uani 0.50 1 d P . .
H19A H 0.9328 -0.1451 0.0512 0.043 Uiso 0.50 1 calc PR . .
H19B H 0.7573 -0.1602 0.0196 0.043 Uiso 0.50 1 calc PR . .
C20 C 0.7963(3) -0.3314(3) -0.07902(18) 0.0436(6) Uani 0.50 1 d P . .
H20A H 0.8539 -0.3927 -0.0747 0.052 Uiso 0.50 1 calc PR . .
H20B H 0.6778 -0.4089 -0.1061 0.052 Uiso 0.50 1 calc PR . .
C21 C 0.8651(4) -0.2419(4) -0.1492(2) 0.0522(7) Uani 0.50 1 d P . .
H21A H 0.8088 -0.1808 -0.1540 0.078 Uiso 0.50 1 calc PR . .
H21B H 0.8473 -0.3186 -0.2140 0.078 Uiso 0.50 1 calc PR . .
H21C H 0.9837 -0.1687 -0.1247 0.078 Uiso 0.50 1 calc PR . .
B1 B 0.1408(3) 0.3071(3) 0.44610(18) 0.0283(5) Uani 0.50 1 d P . .
N1 N 0.5714(2) 0.0997(2) 0.38539(12) 0.0247(4) Uani 0.50 1 d P . .
N2 N 0.6146(2) -0.1021(2) 0.37318(12) 0.0257(4) Uani 0.50 1 d P . .
F1 F 0.05949(17) 0.14157(15) 0.42677(11) 0.0393(4) Uani 0.50 1 d P . .
F2 F 0.28466(18) 0.3523(2) 0.40928(12) 0.0500(4) Uani 0.50 1 d P . .
F3 F 0.03494(18) 0.34555(18) 0.40328(11) 0.0440(4) Uani 0.50 1 d P . .
F4 F 0.18008(17) 0.38449(15) 0.54690(9) 0.0379(4) Uani 0.50 1 d P . .
 
 
_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 N1 1.320(3) . ?
C1 N2 1.331(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(3) . ?
C2 C7 1.394(3) . ?
C2 N1 1.397(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 N2 1.396(3) . ?
C8 N1 1.476(3) . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N2 1.472(3) . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.517(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.530(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.520(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 F2 1.387(3) . ?
B1 F3 1.388(3) . ?
B1 F4 1.389(3) . ?
B1 F1 1.403(3) . ?
 
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
N1 C1 N2 111.19(19) . . ?
N1 C1 H1 124.4 . . ?
N2 C1 H1 124.4 . . ?
C3 C2 C7 121.9(2) . . ?
C3 C2 N1 131.4(2) . . ?
C7 C2 N1 106.62(18) . . ?
C4 C3 C2 116.2(2) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 116.2(2) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
C2 C7 C6 121.8(2) . . ?
C2 C7 N2 106.36(18) . . ?
C6 C7 N2 131.7(2) . . ?
N1 C8 C9 111.39(17) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 113.23(19) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.13(19) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 113.10(19) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 114.2(2) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 112.7(2) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
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 . . ?
N2 C15 C16 112.08(18) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 114.80(18) . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 112.42(19) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 114.13(19) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113.8(2) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 113.6(2) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 B1 F3 110.7(2) . . ?
F2 B1 F4 109.26(19) . . ?
F3 B1 F4 109.74(19) . . ?
F2 B1 F1 110.13(19) . . ?
F3 B1 F1 108.55(19) . . ?
F4 B1 F1 108.46(19) . . ?
C1 N1 C2 107.96(17) . . ?
C1 N1 C8 126.38(18) . . ?
C2 N1 C8 125.62(18) . . ?
C1 N2 C7 107.87(18) . . ?
C1 N2 C15 126.29(18) . . ?
C7 N2 C15 125.85(18) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.207
_refine_diff_density_min   -0.202
_refine_diff_density_rms    0.041
