 
data_2009src0712r
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C25 H23 B O2 P, Br' 
_chemical_formula_sum
 'C25 H23 B Br O2 P'
_chemical_formula_weight          477.12
 
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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br'  'Br'  -0.2901   2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P n'
_symmetry_space_group_name_Hall   'P -2yac'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x+1/2, -y, z+1/2'
 
_cell_length_a                    9.8278(4)
_cell_length_b                    9.4884(5)
_cell_length_c                    12.0388(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.740(3)
_cell_angle_gamma                 90.00
_cell_volume                      1118.78(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     44453
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        shard
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              488
_exptl_absorpt_coefficient_mu     1.928
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.5127
_exptl_absorpt_correction_T_max   0.9810
_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: 0.5969 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             15595
_diffrn_reflns_av_R_equivalents   0.0613
_diffrn_reflns_av_sigmaI/netI     0.0786
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.40
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4905
_reflns_number_gt                 4183
_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, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     
'CrystalMaker (CrystalMaker Software Ltd, 2009'
_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)+(0.0235P)²+0.0000P] 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    0.040(8)
_refine_ls_number_reflns          4905
_refine_ls_number_parameters      273
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0565
_refine_ls_R_factor_gt            0.0428
_refine_ls_wR_factor_ref          0.0846
_refine_ls_wR_factor_gt           0.0799
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_restrained_S_all       1.044
_refine_ls_shift/su_max           0.000
_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
Br1 Br 0.88938(5) 0.51480(4) 0.67793(4) 0.03051(11) Uani 1 1 d . . .
C1 C 0.2774(3) 0.7812(4) 0.4889(3) 0.0212(8) Uani 1 1 d . . .
C2 C 0.3588(4) 0.6649(4) 0.4690(3) 0.0259(8) Uani 1 1 d . . .
H2 H 0.3595 0.6277 0.3958 0.031 Uiso 1 1 calc R . .
C3 C 0.4380(4) 0.6041(4) 0.5558(3) 0.0295(9) Uani 1 1 d . . .
H3 H 0.4948 0.5260 0.5419 0.035 Uiso 1 1 calc R . .
C4 C 0.4355(4) 0.6565(4) 0.6642(3) 0.0290(9) Uani 1 1 d . . .
H4 H 0.4901 0.6147 0.7241 0.035 Uiso 1 1 calc R . .
C5 C 0.3519(4) 0.7706(4) 0.6829(3) 0.0308(9) Uani 1 1 d . . .
H5 H 0.3489 0.8062 0.7565 0.037 Uiso 1 1 calc R . .
C6 C 0.2734(4) 0.8328(4) 0.5967(3) 0.0277(9) Uani 1 1 d . . .
H6 H 0.2167 0.9109 0.6106 0.033 Uiso 1 1 calc R . .
C7 C 0.0207(3) 0.7873(4) 0.3384(3) 0.0220(8) Uani 1 1 d . . .
C8 C -0.0238(4) 0.6732(4) 0.3993(3) 0.0246(8) Uani 1 1 d . . .
H8 H 0.0323 0.6375 0.4610 0.029 Uiso 1 1 calc R . .
C9 C -0.1500(4) 0.6118(4) 0.3696(3) 0.0287(9) Uani 1 1 d . . .
H9 H -0.1795 0.5332 0.4102 0.034 Uiso 1 1 calc R . .
C10 C -0.2326(4) 0.6651(4) 0.2810(3) 0.0294(9) Uani 1 1 d . . .
H10 H -0.3177 0.6215 0.2595 0.035 Uiso 1 1 calc R . .
C11 C -0.1914(4) 0.7824(4) 0.2232(3) 0.0278(8) Uani 1 1 d . . .
H11 H -0.2504 0.8209 0.1644 0.033 Uiso 1 1 calc R . .
C12 C -0.0642(4) 0.8440(4) 0.2508(3) 0.0241(8) Uani 1 1 d . . .
H12 H -0.0357 0.9234 0.2106 0.029 Uiso 1 1 calc R . .
C13 C 0.1506(4) 1.0474(3) 0.4153(3) 0.0202(7) Uani 1 1 d . . .
C14 C 0.0300(4) 1.0885(4) 0.4571(3) 0.0254(8) Uani 1 1 d . . .
H14 H -0.0419 1.0223 0.4612 0.031 Uiso 1 1 calc R . .
C15 C 0.0133(3) 1.2252(4) 0.4927(3) 0.0282(9) Uani 1 1 d . . .
H15 H -0.0688 1.2517 0.5237 0.034 Uiso 1 1 calc R . .
C16 C 0.1151(4) 1.3237(4) 0.4835(3) 0.0285(8) Uani 1 1 d . . .
H16 H 0.1024 1.4178 0.5075 0.034 Uiso 1 1 calc R . .
C17 C 0.2353(4) 1.2861(4) 0.4395(3) 0.0327(10) Uani 1 1 d . . .
H17 H 0.3042 1.3547 0.4314 0.039 Uiso 1 1 calc R . .
C18 C 0.2554(4) 1.1472(4) 0.4071(3) 0.0303(9) Uani 1 1 d . . .
H18 H 0.3393 1.1199 0.3795 0.036 Uiso 1 1 calc R . .
C19 C 0.2885(4) 0.8650(4) 0.2575(3) 0.0230(8) Uani 1 1 d . . .
H19A H 0.3730 0.9185 0.2791 0.028 Uiso 1 1 calc R . .
H19B H 0.3154 0.7658 0.2461 0.028 Uiso 1 1 calc R . .
C20 C 0.2284(3) 0.9219(4) 0.1469(3) 0.0211(7) Uani 1 1 d . . .
C21 C 0.2280(4) 1.0666(4) 0.1232(3) 0.0249(8) Uani 1 1 d . . .
H21 H 0.2602 1.1317 0.1793 0.030 Uiso 1 1 calc R . .
C22 C 0.1816(4) 1.1148(4) 0.0194(3) 0.0286(9) Uani 1 1 d . . .
H22 H 0.1794 1.2131 0.0047 0.034 Uiso 1 1 calc R . .
C23 C 0.1379(6) 1.0204(4) -0.0639(5) 0.0244(9) Uani 1 1 d . . .
H23 H 0.1095 1.0550 -0.1361 0.029 Uiso 1 1 calc R . .
C24 C 0.1347(3) 0.8753(4) -0.0439(3) 0.0225(8) Uani 1 1 d . . .
C25 C 0.1804(3) 0.8286(4) 0.0642(3) 0.0209(7) Uani 1 1 d . . .
H25 H 0.1781 0.7307 0.0806 0.025 Uiso 1 1 calc R . .
B1 B 0.0811(4) 0.7678(5) -0.1380(3) 0.0236(9) Uani 1 1 d . . .
O2 O 0.0278(2) 0.8215(3) -0.23696(19) 0.0271(6) Uani 1 1 d . . .
H2A H -0.0107 0.7569 -0.2755 0.041 Uiso 1 1 calc R . .
O3 O 0.0867(3) 0.6282(3) -0.1125(2) 0.0292(6) Uani 1 1 d . . .
H3A H 0.0410 0.5825 -0.1623 0.044 Uiso 1 1 calc R . .
P1 P 0.18209(9) 0.86970(10) 0.37418(7) 0.0202(2) 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
C1 C6 1.391(5) . ?
C1 C2 1.395(5) . ?
C1 P1 1.810(4) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.397(5) . ?
C7 C8 1.398(5) . ?
C7 P1 1.788(4) . ?
C8 C9 1.390(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 C18 1.408(5) . ?
C13 P1 1.791(3) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.510(5) . ?
C19 P1 1.820(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.387(5) . ?
C20 C21 1.403(5) . ?
C21 C22 1.372(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.412(5) . ?
C24 B1 1.582(6) . ?
C25 H25 0.9500 . ?
B1 O3 1.359(5) . ?
B1 O2 1.361(5) . ?
O2 H2A 0.8400 . ?
O3 H3A 0.8400 . ?
 
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
C6 C1 C2 120.0(3) . . ?
C6 C1 P1 119.7(3) . . ?
C2 C1 P1 120.3(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 120.0(3) . . ?
C12 C7 P1 118.4(3) . . ?
C8 C7 P1 121.5(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.1(3) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C14 C13 C18 119.3(3) . . ?
C14 C13 P1 122.6(3) . . ?
C18 C13 P1 118.0(3) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.8(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C20 C19 P1 117.6(2) . . ?
C20 C19 H19A 107.9 . . ?
P1 C19 H19A 107.9 . . ?
C20 C19 H19B 107.9 . . ?
P1 C19 H19B 107.9 . . ?
H19A C19 H19B 107.2 . . ?
C25 C20 C21 118.9(3) . . ?
C25 C20 C19 119.3(3) . . ?
C21 C20 C19 121.6(3) . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 121.4(5) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 117.2(4) . . ?
C23 C24 B1 121.5(4) . . ?
C25 C24 B1 121.2(3) . . ?
C20 C25 C24 121.7(3) . . ?
C20 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
O3 B1 O2 124.6(4) . . ?
O3 B1 C24 117.5(3) . . ?
O2 B1 C24 117.8(3) . . ?
B1 O2 H2A 109.5 . . ?
B1 O3 H3A 109.5 . . ?
C7 P1 C13 107.95(17) . . ?
C7 P1 C1 111.95(16) . . ?
C13 P1 C1 108.42(17) . . ?
C7 P1 C19 110.97(17) . . ?
C13 P1 C19 111.09(16) . . ?
C1 P1 C19 106.47(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.290
_refine_diff_density_min   -0.483
_refine_diff_density_rms    0.075
