data_2008src0076

#Dr. N. Tomkinson

#The tetrafluoroborate anion is highly disordered. It was calculated 
#for 3 major positions.
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H25 B F4 N2 O'
_chemical_formula_weight          420.25
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.7751(3)
_cell_length_b                    12.8596(4)
_cell_length_c                    16.8243(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2114.88(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12505
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Block'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.17
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.320
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              880
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9713
_exptl_absorpt_correction_T_max   0.9824
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6728 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;
 
_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    'graphite'
_diffrn_measurement_device_type   
 'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18778
_diffrn_reflns_av_R_equivalents   0.0552
_diffrn_reflns_av_sigmaI/netI     0.0381
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.17
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2740
_reflns_number_gt                 2295
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0511P)²+0.5286P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    ?
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          2740
_refine_ls_number_parameters      344
_refine_ls_number_restraints      419
_refine_ls_R_factor_all           0.0557
_refine_ls_R_factor_gt            0.0418
_refine_ls_wR_factor_ref          0.1029
_refine_ls_wR_factor_gt           0.0950
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_restrained_S_all       1.010
_refine_ls_shift/su_max           0.016
_refine_ls_shift/su_mean          0.001
 
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 0.3298(3) 0.81886(17) 0.95671(12) 0.0230(5) Uani 1 1 d . . .
C2 C 0.4779(2) 0.82090(17) 0.93061(12) 0.0224(5) Uani 1 1 d . . .
H2 H 0.5181 0.7495 0.9339 0.027 Uiso 1 1 calc R . .
C3 C 0.3222(2) 0.88416(17) 0.82470(12) 0.0211(5) Uani 1 1 d . . .
C4 C 0.2716(3) 0.81714(19) 0.75586(14) 0.0282(5) Uani 1 1 d . . .
H4A H 0.2960 0.7443 0.7656 0.042 Uiso 1 1 calc R . .
H4B H 0.3144 0.8406 0.7063 0.042 Uiso 1 1 calc R . .
H4C H 0.1720 0.8234 0.7514 0.042 Uiso 1 1 calc R . .
C5 C 0.3134(3) 0.99962(17) 0.80493(14) 0.0248(5) Uani 1 1 d . . .
H5A H 0.2202 1.0165 0.7877 0.037 Uiso 1 1 calc R . .
H5B H 0.3779 1.0160 0.7621 0.037 Uiso 1 1 calc R . .
H5C H 0.3363 1.0406 0.8522 0.037 Uiso 1 1 calc R . .
C6 C 0.1059(3) 0.8791(2) 0.90953(15) 0.0324(6) Uani 1 1 d . . .
H6A H 0.0812 0.8678 0.9653 0.049 Uiso 1 1 calc R . .
H6B H 0.0522 0.8322 0.8758 0.049 Uiso 1 1 calc R . .
H6C H 0.0864 0.9513 0.8949 0.049 Uiso 1 1 calc R . .
C7 C 0.5619(2) 0.89723(18) 0.98186(13) 0.0269(5) Uani 1 1 d . . .
H7A H 0.5618 0.8722 1.0375 0.032 Uiso 1 1 calc R . .
H7B H 0.6578 0.8968 0.9630 0.032 Uiso 1 1 calc R . .
C8 C 0.5096(2) 1.00771(18) 0.98034(13) 0.0245(5) Uani 1 1 d . . .
C9 C 0.5769(3) 1.0829(2) 0.93589(15) 0.0335(6) Uani 1 1 d . . .
H9 H 0.6595 1.0656 0.9093 0.040 Uiso 1 1 calc R . .
C10 C 0.5249(3) 1.1834(2) 0.92978(16) 0.0398(7) Uani 1 1 d . . .
H10 H 0.5726 1.2340 0.8994 0.048 Uiso 1 1 calc R . .
C11 C 0.4044(3) 1.2099(2) 0.96764(14) 0.0384(7) Uani 1 1 d . . .
H11 H 0.3678 1.2779 0.9623 0.046 Uiso 1 1 calc R . .
C12 C 0.3377(3) 1.13630(19) 1.01342(14) 0.0338(6) Uani 1 1 d . . .
H12 H 0.2555 1.1543 1.0403 0.041 Uiso 1 1 calc R . .
C13 C 0.3900(3) 1.03618(18) 1.02038(14) 0.0265(5) Uani 1 1 d . . .
H13 H 0.3441 0.9866 1.0527 0.032 Uiso 1 1 calc R . .
C14 C 0.5611(2) 0.84369(16) 0.79304(12) 0.0216(5) Uani 1 1 d . . .
H14 H 0.5428 0.8714 0.7418 0.026 Uiso 1 1 calc R . .
C15 C 0.6901(2) 0.79516(17) 0.80470(13) 0.0222(5) Uani 1 1 d . . .
H15 H 0.7200 0.7744 0.8560 0.027 Uiso 1 1 calc R . .
C16 C 0.7685(2) 0.77978(17) 0.73943(13) 0.0223(5) Uani 1 1 d . . .
H16 H 0.7417 0.8154 0.6925 0.027 Uiso 1 1 calc R . .
C17 C 0.8893(2) 0.71445(17) 0.73371(13) 0.0213(5) Uani 1 1 d . . .
C18 C 0.9398(2) 0.65744(17) 0.79826(13) 0.0242(5) Uani 1 1 d . . .
H18 H 0.9003 0.6662 0.8494 0.029 Uiso 1 1 calc R . .
C19 C 1.0472(3) 0.58812(18) 0.78783(14) 0.0271(5) Uani 1 1 d . . .
H19 H 1.0809 0.5494 0.8317 0.032 Uiso 1 1 calc R . .
C20 C 1.1056(3) 0.57548(18) 0.71285(14) 0.0288(5) Uani 1 1 d . . .
H20 H 1.1788 0.5278 0.7057 0.035 Uiso 1 1 calc R . .
C21 C 1.0572(3) 0.63237(19) 0.64862(14) 0.0282(5) Uani 1 1 d . . .
H21 H 1.0974 0.6235 0.5976 0.034 Uiso 1 1 calc R . .
C22 C 0.9506(2) 0.70209(18) 0.65868(13) 0.0251(5) Uani 1 1 d . . .
H22 H 0.9188 0.7417 0.6147 0.030 Uiso 1 1 calc R . .
N1 N 0.2518(2) 0.85786(14) 0.89850(11) 0.0227(4) Uani 1 1 d . . .
N2 N 0.4660(2) 0.85340(14) 0.84653(10) 0.0200(4) Uani 1 1 d . . .
O1 O 0.29102(18) 0.79039(12) 1.02258(9) 0.0295(4) Uani 1 1 d . . .
B1 B 0.5814(6) 1.0149(5) 0.6053(4) 0.0343(9) Uani 0.669(4) 1 d PDU A 1
F1 F 0.4724(7) 0.9466(5) 0.6179(6) 0.0504(10) Uani 0.669(4) 1 d PDU A 1
F2 F 0.6043(7) 1.0282(9) 0.5260(3) 0.0681(18) Uani 0.669(4) 1 d PDU A 1
F3 F 0.6946(6) 0.9696(5) 0.6410(5) 0.0671(17) Uani 0.669(4) 1 d PDU A 1
F4 F 0.5566(9) 1.1065(3) 0.6429(4) 0.0892(16) Uani 0.669(4) 1 d PDU A 1
B11 B 0.5976(18) 1.0119(12) 0.6153(9) 0.0343(9) Uani 0.156(7) 1 d PDU B 2
F11 F 0.491(3) 0.9420(19) 0.6155(16) 0.0504(10) Uani 0.156(7) 1 d PDU B 2
F12 F 0.590(2) 1.0786(13) 0.5530(12) 0.074(5) Uani 0.156(7) 1 d PDU B 2
F13 F 0.718(2) 0.9585(15) 0.6035(11) 0.047(4) Uani 0.156(7) 1 d PDU B 2
F14 F 0.6010(17) 1.0652(16) 0.6855(11) 0.062(5) Uani 0.156(7) 1 d PDU B 2
B21 B 0.5625(17) 1.0141(12) 0.6098(10) 0.0343(9) Uani 0.175(7) 1 d PDU C 3
F21 F 0.490(2) 0.9218(12) 0.6152(19) 0.0504(10) Uani 0.175(7) 1 d PDU C 3
F22 F 0.627(2) 1.019(3) 0.5381(11) 0.079(6) Uani 0.175(7) 1 d PDU C 3
F23 F 0.657(2) 1.0163(15) 0.6704(12) 0.074(5) Uani 0.175(7) 1 d PDU C 3
F24 F 0.470(2) 1.0932(10) 0.6187(9) 0.065(5) Uani 0.175(7) 1 d PDU C 3
 
 
_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
C1 O1 1.227(3) . ?
C1 N1 1.338(3) . ?
C1 C2 1.513(3) . ?
C2 N2 1.480(3) . ?
C2 C7 1.543(3) . ?
C2 H2 1.0000 . ?
C3 N1 1.459(3) . ?
C3 N2 1.505(3) . ?
C3 C5 1.524(3) . ?
C3 C4 1.526(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.465(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.510(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.389(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.300(3) . ?
C14 C15 1.420(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.354(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.452(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(3) . ?
C17 C22 1.406(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
B1 F4 1.359(6) . ?
B1 F2 1.363(5) . ?
B1 F3 1.388(6) . ?
B1 F1 1.397(5) . ?
B11 F12 1.357(11) . ?
B11 F14 1.366(10) . ?
B11 F11 1.377(10) . ?
B11 F13 1.378(11) . ?
B21 F22 1.363(10) . ?
B21 F24 1.367(10) . ?
B21 F23 1.377(10) . ?
B21 F21 1.387(10) . ?
 
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
O1 C1 N1 126.6(2) . . ?
O1 C1 C2 124.2(2) . . ?
N1 C1 C2 109.02(18) . . ?
N2 C2 C1 101.94(18) . . ?
N2 C2 C7 113.36(19) . . ?
C1 C2 C7 110.98(18) . . ?
N2 C2 H2 110.1 . . ?
C1 C2 H2 110.1 . . ?
C7 C2 H2 110.1 . . ?
N1 C3 N2 99.88(16) . . ?
N1 C3 C5 112.62(19) . . ?
N2 C3 C5 111.24(19) . . ?
N1 C3 C4 111.22(19) . . ?
N2 C3 C4 109.84(19) . . ?
C5 C3 C4 111.47(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 114.12(19) . . ?
C8 C7 H7A 108.7 . . ?
C2 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C2 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 118.2(2) . . ?
C9 C8 C7 120.3(2) . . ?
C13 C8 C7 121.4(2) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
N2 C14 C15 125.6(2) . . ?
N2 C14 H14 117.2 . . ?
C15 C14 H14 117.2 . . ?
C16 C15 C14 117.1(2) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C15 C16 C17 126.8(2) . . ?
C15 C16 H16 116.6 . . ?
C17 C16 H16 116.6 . . ?
C18 C17 C22 119.1(2) . . ?
C18 C17 C16 122.6(2) . . ?
C22 C17 C16 118.1(2) . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C1 N1 C3 116.17(19) . . ?
C1 N1 C6 122.1(2) . . ?
C3 N1 C6 121.6(2) . . ?
C14 N2 C2 125.3(2) . . ?
C14 N2 C3 121.60(18) . . ?
C2 N2 C3 112.41(17) . . ?
F4 B1 F2 112.1(5) . . ?
F4 B1 F3 107.7(5) . . ?
F2 B1 F3 110.2(5) . . ?
F4 B1 F1 109.8(5) . . ?
F2 B1 F1 110.7(5) . . ?
F3 B1 F1 106.2(4) . . ?
F12 B11 F14 110.6(11) . . ?
F12 B11 F11 111.8(12) . . ?
F14 B11 F11 110.1(11) . . ?
F12 B11 F13 104.6(14) . . ?
F14 B11 F13 110.7(11) . . ?
F11 B11 F13 108.8(11) . . ?
F22 B21 F24 111.7(11) . . ?
F22 B21 F23 110.0(11) . . ?
F24 B21 F23 110.3(10) . . ?
F22 B21 F21 109.6(11) . . ?
F24 B21 F21 106.9(10) . . ?
F23 B21 F21 108.3(11) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.182
_refine_diff_density_min   -0.205
_refine_diff_density_rms    0.044
