 
data_2009src0001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H35 B N2 O4'
_chemical_formula_weight          402.33
 
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'
 'O'  'O'   0.0106   0.0060
 '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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.0998(2)
_cell_length_b                    10.2807(2)
_cell_length_c                    11.7549(3)
_cell_angle_alpha                 100.067(2)
_cell_angle_beta                  100.4290(10)
_cell_angle_gamma                 103.216(2)
_cell_volume                      1138.41(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17992
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.19
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.174
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              436
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9851
_exptl_absorpt_correction_T_max   0.9976
_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             23179
_diffrn_reflns_av_R_equivalents   0.0435
_diffrn_reflns_av_sigmaI/netI     0.0408
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5193
_reflns_number_gt                 4127
_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)+(0.0202P)²+0.8968P] 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          5193
_refine_ls_number_parameters      269
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0740
_refine_ls_R_factor_gt            0.0555
_refine_ls_wR_factor_ref          0.1151
_refine_ls_wR_factor_gt           0.1051
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.070
_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
C3 C 0.23244(18) 0.14851(17) 0.75207(15) 0.0243(4) Uani 1 1 d . . .
C4 C 0.26755(17) 0.30434(17) 0.75277(15) 0.0228(3) Uani 1 1 d . . .
C6 C 0.1353(2) 0.06004(19) 0.63646(17) 0.0344(4) Uani 1 1 d . . .
H6A H 0.0991 -0.0330 0.6468 0.052 Uiso 1 1 calc R . .
H6B H 0.1870 0.0566 0.5735 0.052 Uiso 1 1 calc R . .
H6C H 0.0573 0.0995 0.6146 0.052 Uiso 1 1 calc R . .
C7 C 0.3576(2) 0.0934(2) 0.7860(2) 0.0368(5) Uani 1 1 d . . .
H7A H 0.4125 0.1447 0.8653 0.055 Uiso 1 1 calc R . .
H7B H 0.4159 0.1038 0.7283 0.055 Uiso 1 1 calc R . .
H7C H 0.3253 -0.0039 0.7866 0.055 Uiso 1 1 calc R . .
C8 C 0.39562(18) 0.3902(2) 0.84861(17) 0.0320(4) Uani 1 1 d . . .
H8A H 0.4007 0.4877 0.8557 0.048 Uiso 1 1 calc R . .
H8B H 0.4801 0.3721 0.8271 0.048 Uiso 1 1 calc R . .
H8C H 0.3884 0.3660 0.9247 0.048 Uiso 1 1 calc R . .
C9 C 0.2773(2) 0.3387(2) 0.63357(17) 0.0308(4) Uani 1 1 d . . .
H9A H 0.1876 0.2957 0.5763 0.046 Uiso 1 1 calc R . .
H9B H 0.3508 0.3042 0.6049 0.046 Uiso 1 1 calc R . .
H9C H 0.2997 0.4384 0.6425 0.046 Uiso 1 1 calc R . .
C10 C -0.01702(16) 0.26183(16) 0.92452(14) 0.0194(3) Uani 1 1 d . . .
C11 C -0.02245(18) 0.18710(17) 1.01315(15) 0.0235(4) Uani 1 1 d . . .
H11 H 0.0382 0.1295 1.0226 0.028 Uiso 1 1 calc R . .
C12 C -0.11364(18) 0.19466(18) 1.08745(15) 0.0275(4) Uani 1 1 d . . .
H12 H -0.1144 0.1438 1.1476 0.033 Uiso 1 1 calc R . .
C13 C -0.20388(18) 0.27703(19) 1.07350(16) 0.0287(4) Uani 1 1 d . . .
H13 H -0.2666 0.2833 1.1242 0.034 Uiso 1 1 calc R . .
C14 C -0.20198(17) 0.35024(18) 0.98509(15) 0.0251(4) Uani 1 1 d . . .
H14 H -0.2649 0.4055 0.9751 0.030 Uiso 1 1 calc R . .
C15 C -0.11011(16) 0.34457(16) 0.91071(14) 0.0201(3) Uani 1 1 d . . .
C16 C -0.11173(17) 0.42381(16) 0.81399(14) 0.0216(3) Uani 1 1 d . . .
H16A H -0.1724 0.4861 0.8244 0.026 Uiso 1 1 calc R . .
H16B H -0.0160 0.4806 0.8209 0.026 Uiso 1 1 calc R . .
C18 C -0.12913(17) 0.40442(17) 0.60404(14) 0.0217(3) Uani 1 1 d . . .
H18A H -0.0270 0.4459 0.6215 0.026 Uiso 1 1 calc R . .
H18B H -0.1759 0.4792 0.6040 0.026 Uiso 1 1 calc R . .
C19 C -0.17637(17) 0.30648(18) 0.48310(15) 0.0254(4) Uani 1 1 d . . .
H19A H -0.1585 0.3579 0.4212 0.031 Uiso 1 1 calc R . .
H19B H -0.1222 0.2374 0.4805 0.031 Uiso 1 1 calc R . .
C21 C -0.36542(18) 0.16990(18) 0.55137(15) 0.0262(4) Uani 1 1 d . . .
H21A H -0.3245 0.0913 0.5535 0.031 Uiso 1 1 calc R . .
H21B H -0.4684 0.1345 0.5338 0.031 Uiso 1 1 calc R . .
C22 C -0.31398(16) 0.27125(18) 0.67088(15) 0.0231(4) Uani 1 1 d . . .
H22A H -0.3626 0.3447 0.6711 0.028 Uiso 1 1 calc R . .
H22B H -0.3364 0.2237 0.7341 0.028 Uiso 1 1 calc R . .
C23 C -0.41258(17) 0.23910(17) 0.35795(14) 0.0219(3) Uani 1 1 d . . .
C26 C -0.65818(17) 0.16495(17) 0.25109(15) 0.0235(4) Uani 1 1 d . . .
C27 C -0.6361(2) 0.0959(2) 0.13342(16) 0.0362(5) Uani 1 1 d . . .
H27A H -0.5494 0.1487 0.1189 0.054 Uiso 1 1 calc R . .
H27B H -0.7150 0.0917 0.0693 0.054 Uiso 1 1 calc R . .
H27C H -0.6298 0.0027 0.1361 0.054 Uiso 1 1 calc R . .
C28 C -0.6694(2) 0.3098(2) 0.2547(2) 0.0381(5) Uani 1 1 d . . .
H28A H -0.6725 0.3528 0.3351 0.057 Uiso 1 1 calc R . .
H28B H -0.7549 0.3076 0.1986 0.057 Uiso 1 1 calc R . .
H28C H -0.5881 0.3629 0.2326 0.057 Uiso 1 1 calc R . .
C29 C -0.78644(18) 0.0798(2) 0.28025(17) 0.0311(4) Uani 1 1 d . . .
H29A H -0.7765 -0.0127 0.2808 0.047 Uiso 1 1 calc R . .
H29B H -0.8699 0.0742 0.2202 0.047 Uiso 1 1 calc R . .
H29C H -0.7957 0.1229 0.3586 0.047 Uiso 1 1 calc R . .
B1 B 0.09270(19) 0.24905(19) 0.84861(16) 0.0201(4) Uani 1 1 d . . .
N17 N -0.16313(13) 0.33185(13) 0.69534(12) 0.0192(3) Uani 1 1 d . . .
N20 N -0.32504(15) 0.23747(15) 0.45915(13) 0.0263(3) Uani 1 1 d . . .
O2 O 0.15061(12) 0.14027(12) 0.84241(11) 0.0250(3) Uani 1 1 d . . .
O5 O 0.14750(12) 0.34237(12) 0.78758(10) 0.0229(3) Uani 1 1 d . . .
O24 O -0.37537(13) 0.29982(13) 0.28431(11) 0.0292(3) Uani 1 1 d . . .
O25 O -0.54410(12) 0.16446(12) 0.34952(10) 0.0242(3) 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
C3 O2 1.461(2) . ?
C3 C7 1.517(2) . ?
C3 C6 1.521(3) . ?
C3 C4 1.558(2) . ?
C4 O5 1.4597(19) . ?
C4 C9 1.518(2) . ?
C4 C8 1.524(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.400(2) . ?
C10 C15 1.412(2) . ?
C10 B1 1.557(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.510(2) . ?
C16 N17 1.470(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 N17 1.457(2) . ?
C18 C19 1.516(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N20 1.458(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 N20 1.455(2) . ?
C21 C22 1.518(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N17 1.462(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O24 1.216(2) . ?
C23 O25 1.350(2) . ?
C23 N20 1.353(2) . ?
C26 O25 1.4793(19) . ?
C26 C28 1.513(2) . ?
C26 C27 1.519(2) . ?
C26 C29 1.520(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
B1 O5 1.372(2) . ?
B1 O2 1.373(2) . ?
 
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
O2 C3 C7 109.15(14) . . ?
O2 C3 C6 106.00(14) . . ?
C7 C3 C6 110.84(16) . . ?
O2 C3 C4 102.03(12) . . ?
C7 C3 C4 115.33(15) . . ?
C6 C3 C4 112.66(15) . . ?
O5 C4 C9 108.67(14) . . ?
O5 C4 C8 106.23(13) . . ?
C9 C4 C8 110.46(15) . . ?
O5 C4 C3 101.99(12) . . ?
C9 C4 C3 115.19(15) . . ?
C8 C4 C3 113.47(15) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.96(15) . . ?
C11 C10 B1 117.61(15) . . ?
C15 C10 B1 124.43(15) . . ?
C12 C11 C10 121.94(16) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.54(16) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.56(16) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.47(16) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 119.52(15) . . ?
C14 C15 C16 120.35(15) . . ?
C10 C15 C16 120.12(14) . . ?
N17 C16 C15 111.60(13) . . ?
N17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N17 C18 C19 110.22(13) . . ?
N17 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N17 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N20 C19 C18 110.43(14) . . ?
N20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
N20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N20 C21 C22 109.62(14) . . ?
N20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
N17 C22 C21 110.79(14) . . ?
N17 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
N17 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O24 C23 O25 125.07(15) . . ?
O24 C23 N20 123.47(15) . . ?
O25 C23 N20 111.46(14) . . ?
O25 C26 C28 110.07(14) . . ?
O25 C26 C27 110.01(14) . . ?
C28 C26 C27 113.05(16) . . ?
O25 C26 C29 102.46(13) . . ?
C28 C26 C29 110.10(15) . . ?
C27 C26 C29 110.64(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O5 B1 O2 112.76(15) . . ?
O5 B1 C10 126.37(15) . . ?
O2 B1 C10 120.78(15) . . ?
C18 N17 C22 110.00(12) . . ?
C18 N17 C16 110.97(12) . . ?
C22 N17 C16 110.90(13) . . ?
C23 N20 C21 125.44(14) . . ?
C23 N20 C19 120.38(14) . . ?
C21 N20 C19 114.19(13) . . ?
B1 O2 C3 106.89(13) . . ?
B1 O5 C4 107.16(13) . . ?
C23 O25 C26 119.61(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.265
_refine_diff_density_min   -0.251
_refine_diff_density_rms    0.048
