data_03src0660
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H39 N2, B F4'
_chemical_formula_sum
 'C23 H39 B F4 N2'
_chemical_formula_weight          430.37
 
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                    9.30640(10)
_cell_length_b                    9.8372(2)
_cell_length_c                    15.4960(4)
_cell_angle_alpha                 96.2045(7)
_cell_angle_beta                  102.3108(8)
_cell_angle_gamma                 115.3996(14)
_cell_volume                      1219.63(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12513
_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           0.16
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.172
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              464
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9654
_exptl_absorpt_correction_T_max   0.9965
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source           'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator    '6cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius APEX II CCD camera on κ-goniostat' 
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_reflns_number             21672
_diffrn_reflns_av_R_equivalents   0.1114
_diffrn_reflns_av_sigmaI/netI     0.0700
_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        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          27.44
_reflns_number_total              5496
_reflns_number_gt                 4324
_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 > 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)+(0.0865P)²+0.4748P] 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        0.035(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5496
_refine_ls_number_parameters      274
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0724
_refine_ls_R_factor_gt            0.0570
_refine_ls_wR_factor_ref          0.1637
_refine_ls_wR_factor_gt           0.1495
_refine_ls_goodness_of_fit_ref    0.955
_refine_ls_restrained_S_all       0.955
_refine_ls_shift/su_max           0.012
_refine_ls_shift/su_mean          0.002
 
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
B1 B 0.1751(2) 0.8512(2) 0.05252(13) 0.0248(4) Uani 1 1 d . . .
F1 F 0.13065(13) 0.84636(12) -0.03975(7) 0.0360(3) Uani 1 1 d . . .
F2 F 0.10804(12) 0.69971(11) 0.06494(7) 0.0307(3) Uani 1 1 d . . .
F3 F 0.34684(12) 0.92220(13) 0.08625(8) 0.0438(3) Uani 1 1 d . . .
F4 F 0.10942(14) 0.93012(12) 0.09767(8) 0.0430(3) Uani 1 1 d . . .
C1 C 0.77425(18) 0.65396(17) 0.10696(10) 0.0213(3) Uani 1 1 d . . .
H1 H 0.8825 0.7153 0.1024 0.026 Uiso 1 1 calc R . .
C2 C 0.55228(18) 0.45608(17) 0.11937(9) 0.0195(3) Uani 1 1 d . . .
C3 C 0.43429(19) 0.31367(18) 0.12565(10) 0.0227(3) Uani 1 1 d . . .
H3 H 0.4580 0.2295 0.1301 0.027 Uiso 1 1 calc R . .
C4 C 0.28002(19) 0.30160(19) 0.12503(11) 0.0260(4) Uani 1 1 d . . .
H4 H 0.1950 0.2061 0.1285 0.031 Uiso 1 1 calc R . .
C5 C 0.2463(2) 0.4272(2) 0.11943(11) 0.0276(4) Uani 1 1 d . . .
H5 H 0.1389 0.4138 0.1192 0.033 Uiso 1 1 calc R . .
C6 C 0.36383(19) 0.56926(18) 0.11423(10) 0.0235(3) Uani 1 1 d . . .
H6 H 0.3409 0.6542 0.1113 0.028 Uiso 1 1 calc R . .
C7 C 0.51813(18) 0.58076(17) 0.11354(9) 0.0194(3) Uani 1 1 d . . .
C8 C 0.80630(19) 0.41701(18) 0.11858(10) 0.0237(3) Uani 1 1 d . . .
H8A H 0.8944 0.4601 0.0883 0.028 Uiso 1 1 calc R . .
H8B H 0.7290 0.3093 0.0848 0.028 Uiso 1 1 calc R . .
C9 C 0.88501(19) 0.41697(18) 0.21555(10) 0.0239(3) Uani 1 1 d . . .
H9A H 0.9318 0.3437 0.2137 0.029 Uiso 1 1 calc R . .
H9B H 0.7971 0.3789 0.2464 0.029 Uiso 1 1 calc R . .
C10 C 1.02233(19) 0.57512(18) 0.27171(11) 0.0256(3) Uani 1 1 d . . .
H10A H 1.1094 0.6153 0.2405 0.031 Uiso 1 1 calc R . .
H10B H 0.9754 0.6480 0.2761 0.031 Uiso 1 1 calc R . .
C11 C 1.1007(2) 0.56745(19) 0.36711(11) 0.0278(4) Uani 1 1 d . . .
H11A H 1.0128 0.5258 0.3976 0.033 Uiso 1 1 calc R . .
H11B H 1.1478 0.4948 0.3623 0.033 Uiso 1 1 calc R . .
C12 C 1.2373(2) 0.72347(19) 0.42549(11) 0.0266(4) Uani 1 1 d . . .
H12A H 1.1918 0.7978 0.4277 0.032 Uiso 1 1 calc R . .
H12B H 1.3281 0.7627 0.3967 0.032 Uiso 1 1 calc R . .
C13 C 1.3088(2) 0.71611(19) 0.52235(11) 0.0278(4) Uani 1 1 d . . .
H13A H 1.2181 0.6787 0.5513 0.033 Uiso 1 1 calc R . .
H13B H 1.3517 0.6399 0.5198 0.033 Uiso 1 1 calc R . .
C14 C 1.4477(2) 0.8698(2) 0.58113(11) 0.0301(4) Uani 1 1 d . . .
H14A H 1.4054 0.9465 0.5831 0.036 Uiso 1 1 calc R . .
H14B H 1.5392 0.9066 0.5527 0.036 Uiso 1 1 calc R . .
C15 C 1.5164(2) 0.8615(2) 0.67773(12) 0.0394(5) Uani 1 1 d . . .
H15A H 1.4277 0.8298 0.7074 0.059 Uiso 1 1 calc R . .
H15B H 1.6066 0.9633 0.7115 0.059 Uiso 1 1 calc R . .
H15C H 1.5590 0.7861 0.6764 0.059 Uiso 1 1 calc R . .
C16 C 0.6817(2) 0.85762(17) 0.09973(10) 0.0246(3) Uani 1 1 d . . .
H16A H 0.5788 0.8489 0.0593 0.029 Uiso 1 1 calc R . .
H16B H 0.7733 0.9084 0.0729 0.029 Uiso 1 1 calc R . .
C17 C 0.7210(2) 0.95656(18) 0.19285(11) 0.0258(3) Uani 1 1 d . . .
H17A H 0.6395 0.8972 0.2238 0.031 Uiso 1 1 calc R . .
H17B H 0.7081 1.0496 0.1848 0.031 Uiso 1 1 calc R . .
C18 C 0.8960(2) 1.00687(19) 0.25299(11) 0.0270(4) Uani 1 1 d . . .
H18A H 0.9119 0.9143 0.2570 0.032 Uiso 1 1 calc R . .
H18B H 0.9776 1.0733 0.2244 0.032 Uiso 1 1 calc R . .
C19 C 0.9303(2) 1.09484(19) 0.34841(11) 0.0258(3) Uani 1 1 d . . .
H19A H 0.8552 1.0254 0.3789 0.031 Uiso 1 1 calc R . .
H19B H 0.9051 1.1824 0.3443 0.031 Uiso 1 1 calc R . .
C20 C 1.1095(2) 1.1566(2) 0.40568(11) 0.0282(4) Uani 1 1 d . . .
H20A H 1.1357 1.0693 0.4076 0.034 Uiso 1 1 calc R . .
H20B H 1.1841 1.2287 0.3760 0.034 Uiso 1 1 calc R . .
C21 C 1.1449(2) 1.24004(19) 0.50256(11) 0.0269(4) Uani 1 1 d . . .
H21A H 1.1150 1.3251 0.5007 0.032 Uiso 1 1 calc R . .
H21B H 1.0734 1.1669 0.5330 0.032 Uiso 1 1 calc R . .
C22 C 1.3257(2) 1.3063(2) 0.55826(11) 0.0325(4) Uani 1 1 d . . .
H22A H 1.3972 1.3804 0.5282 0.039 Uiso 1 1 calc R . .
H22B H 1.3561 1.2215 0.5597 0.039 Uiso 1 1 calc R . .
C23 C 1.3594(2) 1.3879(2) 0.65513(12) 0.0394(4) Uani 1 1 d . . .
H23A H 1.3303 1.4725 0.6542 0.059 Uiso 1 1 calc R . .
H23B H 1.4775 1.4296 0.6875 0.059 Uiso 1 1 calc R . .
H23C H 1.2923 1.3142 0.6861 0.059 Uiso 1 1 calc R . .
N1 N 0.71527(15) 0.50797(14) 0.11508(8) 0.0202(3) Uani 1 1 d . . .
N2 N 0.66028(15) 0.70230(14) 0.10608(8) 0.0209(3) 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
B1 F3 1.387(2) . ?
B1 F1 1.391(2) . ?
B1 F4 1.392(2) . ?
B1 F2 1.401(2) . ?
C1 N2 1.334(2) . ?
C1 N1 1.331(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(2) . ?
C2 N1 1.3971(19) . ?
C2 C7 1.400(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 N2 1.390(2) . ?
C8 N1 1.4705(19) . ?
C8 C9 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.528(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.530(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N2 1.4708(19) . ?
C16 C17 1.526(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.522(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
 
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
F3 B1 F1 109.42(14) . . ?
F3 B1 F4 110.77(14) . . ?
F1 B1 F4 109.92(14) . . ?
F3 B1 F2 109.75(14) . . ?
F1 B1 F2 108.75(13) . . ?
F4 B1 F2 108.19(13) . . ?
N2 C1 N1 110.63(13) . . ?
N2 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
C3 C2 N1 131.92(14) . . ?
C3 C2 C7 122.04(14) . . ?
N1 C2 C7 106.02(13) . . ?
C4 C3 C2 116.18(14) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C3 C4 C5 121.63(15) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 122.30(15) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 116.07(14) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
N2 C7 C6 131.24(14) . . ?
N2 C7 C2 106.98(13) . . ?
C6 C7 C2 121.77(14) . . ?
N1 C8 C9 112.25(12) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 114.22(13) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 112.02(13) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 113.54(13) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.15(14) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 114.00(14) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 113.54(15) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 111.25(12) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 113.12(13) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 113.07(13) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 112.89(13) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 113.72(14) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 113.32(14) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 112.93(15) . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C2 108.34(12) . . ?
C1 N1 C8 125.70(13) . . ?
C2 N1 C8 125.96(13) . . ?
C1 N2 C7 108.02(13) . . ?
C1 N2 C16 126.10(13) . . ?
C7 N2 C16 125.86(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.990
_diffrn_reflns_theta_full              27.44
_diffrn_measured_fraction_theta_full   0.990
_refine_diff_density_max    0.307
_refine_diff_density_min   -0.278
_refine_diff_density_rms    0.056
