 
data_2009src0893c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C24 H20 B, C7 H12 N O2'
_chemical_formula_sum
 'C31 H32 B N O2'
_chemical_formula_weight          461.39
 
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            orthorhombic
_symmetry_space_group_name_H-M    'P n m a'
_symmetry_space_group_name_Hall   '-P 2ac 2n'

 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z+1/2'
 '-x, y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z-1/2'
 'x, -y-1/2, z'
 
_cell_length_a                    19.3041(7)
_cell_length_b                    13.1353(5)
_cell_length_c                    10.1462(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2572.72(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     33465
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'Cut Block'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.48
_exptl_crystal_size_mid           0.34
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.191
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              984
_exptl_absorpt_coefficient_mu     0.073
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9659
_exptl_absorpt_correction_T_max   0.9885
_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   '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             18899
_diffrn_reflns_av_R_equivalents   0.0416
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.30
_diffrn_reflns_theta_max          25.00
_reflns_number_total              2360
_reflns_number_gt                 2101
_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     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0681P)²+3.4231P] 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          2360
_refine_ls_number_parameters      212
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0769
_refine_ls_R_factor_gt            0.0699
_refine_ls_wR_factor_ref          0.1720
_refine_ls_wR_factor_gt           0.1670
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_refine_ls_shift/su_max           0.009
_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 -0.2256(2) -0.7838(4) -0.0827(5) 0.0335(12) Uani 0.50 1 d P A -1
H1A H -0.2297 -0.7332 -0.0108 0.040 Uiso 0.50 1 calc PR A -1
H1B H -0.2702 -0.8200 -0.0936 0.040 Uiso 0.50 1 calc PR A -1
C2 C -0.2016(2) -0.7347(15) -0.2113(5) 0.038(4) Uani 0.50 1 d P A -1
H2A H -0.2146 -0.7772 -0.2880 0.045 Uiso 0.50 1 calc PR A -1
H2B H -0.2222 -0.6661 -0.2221 0.045 Uiso 0.50 1 calc PR A -1
C3 C -0.1082(2) -0.7968(4) -0.0739(4) 0.0279(10) Uani 0.50 1 d P A -1
H3 H -0.0983 -0.7553 0.0065 0.033 Uiso 0.50 1 calc PR A -1
C4 C -0.0481(2) -0.8608(4) -0.1119(4) 0.0292(11) Uani 0.50 1 d P A -1
H4A H -0.0489 -0.9266 -0.0643 0.035 Uiso 0.50 1 calc PR A -1
H4B H -0.0040 -0.8255 -0.0922 0.035 Uiso 0.50 1 calc PR A -1
C5 C -0.0565(3) -0.8771(4) -0.2597(5) 0.0310(10) Uani 0.50 1 d P A -1
H5A H -0.0113 -0.8917 -0.3017 0.037 Uiso 0.50 1 calc PR A -1
H5B H -0.0886 -0.9341 -0.2780 0.037 Uiso 0.50 1 calc PR A -1
C6 C -0.0856(2) -0.7784(3) -0.3082(4) 0.0256(12) Uani 0.50 1 d P A -1
C7 C -0.0983(3) -0.6218(4) -0.1721(5) 0.0319(11) Uani 0.50 1 d P A -1
H7A H -0.0484 -0.6231 -0.1540 0.048 Uiso 0.50 1 calc PR A -1
H7B H -0.1228 -0.5934 -0.0959 0.048 Uiso 0.50 1 calc PR A -1
H7C H -0.1073 -0.5796 -0.2498 0.048 Uiso 0.50 1 calc PR A -1
N1 N -0.12337(18) -0.7281(3) -0.1972(3) 0.0245(13) Uani 0.50 1 d P A -1
O1 O -0.16871(16) -0.8538(3) -0.0602(3) 0.0328(8) Uani 0.50 1 d P A -1
O2 O -0.0835(3) -0.7483(10) -0.4274(5) 0.124(3) Uani 1 2 d S A -1
C8 C 0.00786(16) -0.7500 0.2393(3) 0.0200(6) Uani 1 2 d S . .
C9 C -0.03139(12) -0.84009(16) 0.2381(2) 0.0246(5) Uani 1 1 d . . .
H9 H -0.0077 -0.9034 0.2357 0.030 Uiso 1 1 calc R . .
C10 C -0.10346(12) -0.84064(18) 0.2404(2) 0.0300(6) Uani 1 1 d . . .
H10 H -0.1277 -0.9036 0.2402 0.036 Uiso 1 1 calc R . .
C11 C -0.14015(17) -0.7500 0.2428(3) 0.0310(8) Uani 1 2 d S . .
H11 H -0.1893 -0.7500 0.2461 0.037 Uiso 1 2 calc SR . .
C12 C 0.11017(15) -0.7500 0.0727(3) 0.0223(7) Uani 1 2 d S . .
C13 C 0.11449(18) -0.6618(2) -0.0013(3) 0.0507(8) Uani 1 1 d . . .
H13 H 0.1140 -0.5983 0.0435 0.061 Uiso 1 1 calc R . .
C14 C 0.1195(2) -0.6615(2) -0.1384(3) 0.0606(10) Uani 1 1 d . . .
H14 H 0.1217 -0.5984 -0.1840 0.073 Uiso 1 1 calc R . .
C15 C 0.12131(17) -0.7500 -0.2081(3) 0.0370(9) Uani 1 2 d S . .
H15 H 0.1237 -0.7500 -0.3016 0.044 Uiso 1 2 calc SR . .
C16 C 0.12662(11) -0.65214(15) 0.3107(2) 0.0230(5) Uani 1 1 d . . .
C17 C 0.18990(12) -0.60739(17) 0.2754(2) 0.0312(6) Uani 1 1 d . . .
H17 H 0.2121 -0.6292 0.1968 0.037 Uiso 1 1 calc R . .
C18 C 0.22140(13) -0.5321(2) 0.3513(3) 0.0432(7) Uani 1 1 d . . .
H18 H 0.2645 -0.5042 0.3241 0.052 Uiso 1 1 calc R . .
C19 C 0.19039(15) -0.4977(2) 0.4660(3) 0.0439(7) Uani 1 1 d . . .
H19 H 0.2117 -0.4461 0.5176 0.053 Uiso 1 1 calc R . .
C20 C 0.12778(15) -0.53971(19) 0.5040(2) 0.0405(7) Uani 1 1 d . . .
H20 H 0.1057 -0.5166 0.5822 0.049 Uiso 1 1 calc R . .
C21 C 0.09720(13) -0.61535(18) 0.4286(2) 0.0320(6) Uani 1 1 d . . .
H21 H 0.0545 -0.6436 0.4576 0.038 Uiso 1 1 calc R . .
B1 B 0.09306(18) -0.7500 0.2319(3) 0.0216(7) Uani 1 2 d S . .
 
 
_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 O1 1.451(5) . ?
C1 C2 1.527(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.520(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.394(5) . ?
C3 C4 1.483(6) . ?
C3 N1 1.570(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.523(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.496(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.273(8) . ?
C6 N1 1.496(5) . ?
C7 N1 1.499(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.405(3) . ?
C8 C9 1.405(3) 8_545 ?
C8 B1 1.647(4) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C10 1.386(3) 8_545 ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) 8_545 ?
C12 C13 1.383(3) . ?
C12 B1 1.648(4) . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.361(4) . ?
C14 H14 0.9500 . ?
C15 C14 1.361(4) 8_545 ?
C15 H15 0.9500 . ?
C16 C17 1.402(3) . ?
C16 C21 1.409(3) . ?
C16 B1 1.647(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
B1 C16 1.647(3) 8_545 ?
 
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 C2 100.0(5) . . ?
O1 C1 H1A 111.8 . . ?
C2 C1 H1A 111.8 . . ?
O1 C1 H1B 111.8 . . ?
C2 C1 H1B 111.8 . . ?
H1A C1 H1B 109.5 . . ?
N1 C2 C1 104.1(5) . . ?
N1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
O1 C3 C4 112.2(4) . . ?
O1 C3 N1 103.5(3) . . ?
C4 C3 N1 105.3(3) . . ?
O1 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
N1 C3 H3 111.8 . . ?
C3 C4 C5 104.6(4) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C4 104.0(4) . . ?
C6 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
O2 C6 C5 124.7(7) . . ?
O2 C6 N1 126.4(6) . . ?
C5 C6 N1 108.6(3) . . ?
C6 N1 C7 112.5(3) . . ?
C6 N1 C2 112.9(5) . . ?
C7 N1 C2 113.0(8) . . ?
C6 N1 C3 104.7(3) . . ?
C7 N1 C3 109.9(3) . . ?
C2 N1 C3 103.1(5) . . ?
C3 O1 C1 106.1(3) . . ?
C9 C8 C9 114.7(3) . 8_545 ?
C9 C8 B1 122.56(14) . . ?
C9 C8 B1 122.56(14) 8_545 . ?
C10 C9 C8 122.9(2) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C10 118.5(3) 8_545 . ?
C10 C11 H11 120.8 8_545 . ?
C10 C11 H11 120.8 . . ?
C13 C12 C13 113.8(3) 8_545 . ?
C13 C12 B1 122.95(15) 8_545 . ?
C13 C12 B1 122.95(15) . . ?
C12 C13 C14 123.3(3) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C14 117.4(3) 8_545 . ?
C14 C15 H15 121.3 8_545 . ?
C14 C15 H15 121.3 . . ?
C17 C16 C21 115.1(2) . . ?
C17 C16 B1 123.1(2) . . ?
C21 C16 B1 121.4(2) . . ?
C18 C17 C16 122.4(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 122.9(2) . . ?
C20 C21 H21 118.6 . . ?
C16 C21 H21 118.6 . . ?
C8 B1 C16 111.76(17) . . ?
C8 B1 C16 111.76(17) . 8_545 ?
C16 B1 C16 102.6(2) . 8_545 ?
C8 B1 C12 104.2(2) . . ?
C16 B1 C12 113.40(17) . . ?
C16 B1 C12 113.40(17) 8_545 . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.499
_refine_diff_density_min   -0.610
_refine_diff_density_rms    0.050
