 
data_2009src0002r
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H26 B N O3'
_chemical_formula_weight          303.20
 
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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    6.4630(8)
_cell_length_b                    12.9251(14)
_cell_length_c                    20.862(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.690(4)
_cell_angle_gamma                 90.00
_cell_volume                      1739.1(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     35096
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.158
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              656
_exptl_absorpt_coefficient_mu     0.077
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9923
_exptl_absorpt_correction_T_max   0.9985
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_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    '10cm 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_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11528
_diffrn_reflns_av_R_equivalents   0.1001
_diffrn_reflns_av_sigmaI/netI     0.1062
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.15
_diffrn_reflns_theta_max          24.99
_reflns_number_total              3017
_reflns_number_gt                 1725
_reflns_threshold_expression      >2σ(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     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0000P)²+6.2974P] 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          3017
_refine_ls_number_parameters      203
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1909
_refine_ls_R_factor_gt            0.1050
_refine_ls_wR_factor_ref          0.2227
_refine_ls_wR_factor_gt           0.1787
_refine_ls_goodness_of_fit_ref    1.081
_refine_ls_restrained_S_all       1.081
_refine_ls_shift/su_max           0.001
_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
C14 C -0.0405(8) -0.0790(4) 0.0969(2) 0.0371(13) Uani 1 1 d . . .
H14 H -0.1826 -0.0980 0.0967 0.045 Uiso 1 1 calc R . .
C11 C 0.3693(9) -0.0212(4) 0.0989(2) 0.0408(14) Uani 1 1 d . . .
H11 H 0.5110 -0.0018 0.0988 0.049 Uiso 1 1 calc R . .
C15 C 0.0468(8) -0.0209(4) 0.1481(2) 0.0384(13) Uani 1 1 d . . .
H15 H -0.0364 -0.0017 0.1821 0.046 Uiso 1 1 calc R . .
C10 C 0.2541(8) 0.0093(4) 0.1502(2) 0.0359(13) Uani 1 1 d . . .
C13 C 0.0736(8) -0.1096(4) 0.0468(2) 0.0371(13) Uani 1 1 d . . .
C3 C 0.3850(7) 0.1827(4) 0.2916(2) 0.0330(12) Uani 1 1 d . . .
C12 C 0.2809(8) -0.0792(4) 0.0483(2) 0.0407(14) Uani 1 1 d . . .
H12 H 0.3630 -0.0985 0.0141 0.049 Uiso 1 1 calc R . .
C16 C -0.0241(9) -0.1680(4) -0.0102(2) 0.0420(14) Uani 1 1 d . . .
H16A H -0.1562 -0.1992 0.0018 0.050 Uiso 1 1 calc R . .
H16B H -0.0563 -0.1190 -0.0459 0.050 Uiso 1 1 calc R . .
C7 C 0.3409(8) 0.2902(4) 0.2643(2) 0.0427(14) Uani 1 1 d . . .
H7B H 0.3728 0.2918 0.2190 0.064 Uiso 1 1 calc R . .
H7C H 0.4273 0.3411 0.2884 0.064 Uiso 1 1 calc R . .
H7A H 0.1943 0.3071 0.2679 0.064 Uiso 1 1 calc R . .
C4 C 0.5998(8) 0.1418(4) 0.2766(2) 0.0402(14) Uani 1 1 d . . .
C22 C 0.0343(10) -0.2900(5) -0.0952(2) 0.0515(16) Uani 1 1 d . . .
H22B H 0.0259 -0.2334 -0.1272 0.062 Uiso 1 1 calc R . .
H22A H -0.1060 -0.3197 -0.0924 0.062 Uiso 1 1 calc R . .
C9 C 0.6740(9) 0.0508(4) 0.3185(3) 0.0486(15) Uani 1 1 d . . .
H9C H 0.5638 -0.0012 0.3191 0.073 Uiso 1 1 calc R . .
H9A H 0.7090 0.0752 0.3624 0.073 Uiso 1 1 calc R . .
H9B H 0.7970 0.0200 0.3011 0.073 Uiso 1 1 calc R . .
C6 C 0.3380(8) 0.1795(4) 0.3619(2) 0.0411(14) Uani 1 1 d . . .
H6B H 0.1986 0.2071 0.3668 0.062 Uiso 1 1 calc R . .
H6A H 0.4399 0.2216 0.3871 0.062 Uiso 1 1 calc R . .
H6C H 0.3451 0.1079 0.3772 0.062 Uiso 1 1 calc R . .
C21 C 0.1822(11) -0.3722(5) -0.1152(3) 0.0637(19) Uani 1 1 d . . .
H21B H 0.1324 -0.4001 -0.1576 0.076 Uiso 1 1 calc R . .
H21A H 0.3203 -0.3408 -0.1197 0.076 Uiso 1 1 calc R . .
C18 C 0.1258(10) -0.3342(4) 0.0138(2) 0.0546(17) Uani 1 1 d . . .
H18B H -0.0130 -0.3650 0.0179 0.066 Uiso 1 1 calc R . .
H18A H 0.1768 -0.3078 0.0564 0.066 Uiso 1 1 calc R . .
C8 C 0.7669(8) 0.2230(5) 0.2740(3) 0.0507(16) Uani 1 1 d . . .
H8B H 0.8970 0.1902 0.2633 0.076 Uiso 1 1 calc R . .
H8A H 0.7867 0.2572 0.3159 0.076 Uiso 1 1 calc R . .
H8C H 0.7256 0.2744 0.2411 0.076 Uiso 1 1 calc R . .
C19 C 0.2707(13) -0.4148(5) -0.0082(3) 0.076(2) Uani 1 1 d . . .
H19B H 0.4108 -0.3845 -0.0104 0.091 Uiso 1 1 calc R . .
H19A H 0.2803 -0.4721 0.0233 0.091 Uiso 1 1 calc R . .
B1 B 0.3539(9) 0.0739(5) 0.2066(3) 0.0355(15) Uani 1 1 d . . .
N17 N 0.1107(7) -0.2495(3) -0.03210(19) 0.0411(11) Uani 1 1 d . . .
O20 O 0.2012(8) -0.4543(3) -0.07005(19) 0.0769(16) Uani 1 1 d . . .
O2 O 0.2449(5) 0.1112(3) 0.25572(15) 0.0397(9) Uani 1 1 d . . .
O5 O 0.5587(5) 0.0986(3) 0.21153(16) 0.0441(10) Uani 1 1 d . . .
 
 
_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
C14 C13 1.376(7) . ?
C14 C15 1.395(7) . ?
C14 H14 0.9500 . ?
C11 C12 1.388(7) . ?
C11 C10 1.398(7) . ?
C11 H11 0.9500 . ?
C15 C10 1.394(7) . ?
C15 H15 0.9500 . ?
C10 B1 1.549(8) . ?
C13 C12 1.395(7) . ?
C13 C16 1.512(7) . ?
C3 O2 1.466(6) . ?
C3 C6 1.518(6) . ?
C3 C7 1.521(7) . ?
C3 C4 1.536(7) . ?
C12 H12 0.9500 . ?
C16 N17 1.458(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
C4 O5 1.476(6) . ?
C4 C8 1.510(7) . ?
C4 C9 1.524(7) . ?
C22 N17 1.471(6) . ?
C22 C21 1.506(8) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C9 H9C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6C 0.9800 . ?
C21 O20 1.419(7) . ?
C21 H21B 0.9900 . ?
C21 H21A 0.9900 . ?
C18 N17 1.453(7) . ?
C18 C19 1.492(8) . ?
C18 H18B 0.9900 . ?
C18 H18A 0.9900 . ?
C8 H8B 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8C 0.9800 . ?
C19 O20 1.434(7) . ?
C19 H19B 0.9900 . ?
C19 H19A 0.9900 . ?
B1 O5 1.359(7) . ?
B1 O2 1.367(7) . ?
 
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
C13 C14 C15 121.8(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C10 C15 C14 121.1(5) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C10 C11 117.0(5) . . ?
C15 C10 B1 121.8(5) . . ?
C11 C10 B1 121.1(5) . . ?
C14 C13 C12 117.6(5) . . ?
C14 C13 C16 121.6(5) . . ?
C12 C13 C16 120.7(5) . . ?
O2 C3 C6 108.7(4) . . ?
O2 C3 C7 106.9(4) . . ?
C6 C3 C7 110.0(4) . . ?
O2 C3 C4 102.4(4) . . ?
C6 C3 C4 115.3(4) . . ?
C7 C3 C4 112.9(4) . . ?
C11 C12 C13 121.1(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N17 C16 C13 112.3(4) . . ?
N17 C16 H16A 109.1 . . ?
C13 C16 H16A 109.1 . . ?
N17 C16 H16B 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
O5 C4 C8 108.5(4) . . ?
O5 C4 C9 105.5(4) . . ?
C8 C4 C9 110.9(5) . . ?
O5 C4 C3 101.9(4) . . ?
C8 C4 C3 115.2(5) . . ?
C9 C4 C3 113.8(5) . . ?
N17 C22 C21 108.5(5) . . ?
N17 C22 H22B 110.0 . . ?
C21 C22 H22B 110.0 . . ?
N17 C22 H22A 110.0 . . ?
C21 C22 H22A 110.0 . . ?
H22B C22 H22A 108.4 . . ?
C4 C9 H9C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
O20 C21 C22 111.9(5) . . ?
O20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
O20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
H21B C21 H21A 107.9 . . ?
N17 C18 C19 109.9(5) . . ?
N17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
N17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
H18B C18 H18A 108.2 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
O20 C19 C18 111.0(5) . . ?
O20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
O20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
H19B C19 H19A 108.0 . . ?
O5 B1 O2 114.0(5) . . ?
O5 B1 C10 122.6(5) . . ?
O2 B1 C10 123.3(5) . . ?
C18 N17 C16 110.7(4) . . ?
C18 N17 C22 109.0(4) . . ?
C16 N17 C22 111.4(4) . . ?
C21 O20 C19 109.8(5) . . ?
B1 O2 C3 105.9(4) . . ?
B1 O5 C4 105.9(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.983
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.983
_refine_diff_density_max    0.304
_refine_diff_density_min   -0.308
_refine_diff_density_rms    0.066
