data_02src154
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Allen
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C33 H25 Br N O2 P'
_chemical_formula_weight          578.42
 
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'
 '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'
 '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    C2/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    26.860(3)
_cell_length_b                    10.0338(9)
_cell_length_c                    22.976(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  124.152(11)
_cell_angle_gamma                 90.00
_cell_volume                      5124.3(10)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     68062
_cell_measurement_theta_min       1.02
_cell_measurement_theta_max       21.97
 
_exptl_crystal_description        plate
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.500
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2368
_exptl_absorpt_coefficient_mu     1.700
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8484
_exptl_absorpt_correction_T_max   0.9832
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_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 KappaCCD'
_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             9294
_diffrn_reflns_av_R_equivalents   0.0739
_diffrn_reflns_av_sigmaI/netI     0.0721
_diffrn_reflns_limit_h_min        -28
_diffrn_reflns_limit_h_max        28
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.23
_diffrn_reflns_theta_max          21.96
_reflns_number_total              3107
_reflns_number_gt                 2378
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0524P)²+19.9846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.00000(12)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3107
_refine_ls_number_parameters      353
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0726
_refine_ls_R_factor_gt            0.0493
_refine_ls_wR_factor_ref          0.1219
_refine_ls_wR_factor_gt           0.1085
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.011
_refine_ls_shift/su_max           3.959
_refine_ls_shift/su_mean          0.013
 
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
H1B H -0.056(3) 0.093(6) -0.012(3) 0.01(2) Uiso 1 1 d . . .
H1A H -0.067(3) 0.012(8) 0.025(4) 0.08(3) Uiso 1 1 d . . .
Br1 Br 0.15436(2) 0.16055(5) 0.03212(3) 0.0341(3) Uani 1 1 d . . .
C1 C 0.1031(2) 0.2504(5) 0.1949(3) 0.0278(13) Uani 1 1 d . . .
C2 C 0.0732(2) 0.1409(5) 0.1997(3) 0.0286(13) Uani 1 1 d . . .
H2 H 0.0881 0.1051 0.2449 0.034 Uiso 1 1 calc R . .
C3 C 0.0237(2) 0.0830(5) 0.1424(3) 0.0273(13) Uani 1 1 d . . .
C4 C -0.0082(2) -0.0317(5) 0.1507(3) 0.0329(14) Uani 1 1 d . . .
H4A H 0.0130 -0.0551 0.2006 0.049 Uiso 1 1 calc R . .
H4B H -0.0086 -0.1088 0.1243 0.049 Uiso 1 1 calc R . .
H4C H -0.0496 -0.0056 0.1327 0.049 Uiso 1 1 calc R . .
C5 C 0.0026(2) 0.1300(5) 0.0737(3) 0.0289(14) Uani 1 1 d . . .
C6 C 0.0339(2) 0.2374(5) 0.0667(3) 0.0281(13) Uani 1 1 d . . .
C7 C 0.0166(2) 0.2818(5) -0.0032(3) 0.0303(14) Uani 1 1 d . . .
C8 C 0.0490(2) 0.3973(5) -0.0083(3) 0.0277(13) Uani 1 1 d . . .
C9 C 0.0349(2) 0.4370(5) -0.0736(3) 0.0344(14) Uani 1 1 d . . .
H9 H 0.0053 0.3900 -0.1147 0.041 Uiso 1 1 calc R . .
C10 C 0.0643(3) 0.5463(5) -0.0789(3) 0.0368(15) Uani 1 1 d . . .
H10 H 0.0560 0.5712 -0.1234 0.044 Uiso 1 1 calc R . .
C11 C 0.1053(3) 0.6181(5) -0.0197(3) 0.0378(15) Uani 1 1 d . . .
H11 H 0.1241 0.6942 -0.0240 0.045 Uiso 1 1 calc R . .
C12 C 0.1195(2) 0.5807(5) 0.0460(3) 0.0316(14) Uani 1 1 d . . .
H12 H 0.1476 0.6308 0.0866 0.038 Uiso 1 1 calc R . .
C13 C 0.0919(2) 0.4687(5) 0.0519(3) 0.0269(13) Uani 1 1 d . . .
C14 C 0.1095(2) 0.4235(5) 0.1215(3) 0.0278(13) Uani 1 1 d . . .
C15 C 0.0821(2) 0.2986(5) 0.1274(3) 0.0265(13) Uani 1 1 d . . .
C16 C 0.1475(2) 0.4639(5) 0.3047(3) 0.0262(13) Uani 1 1 d . . .
C17 C 0.1835(2) 0.5085(5) 0.3737(3) 0.0321(14) Uani 1 1 d . . .
H17 H 0.2197 0.4632 0.4068 0.038 Uiso 1 1 calc R . .
C18 C 0.1660(2) 0.6204(5) 0.3939(3) 0.0312(14) Uani 1 1 d . . .
H18 H 0.1904 0.6513 0.4410 0.037 Uiso 1 1 calc R . .
C19 C 0.1142(2) 0.6856(5) 0.3464(3) 0.0331(14) Uani 1 1 d . . .
H19 H 0.1028 0.7619 0.3609 0.040 Uiso 1 1 calc R . .
C20 C 0.0781(2) 0.6429(5) 0.2780(3) 0.0340(14) Uani 1 1 d . . .
H20 H 0.0423 0.6903 0.2452 0.041 Uiso 1 1 calc R . .
C21 C 0.0939(2) 0.5304(5) 0.2568(3) 0.0323(14) Uani 1 1 d . . .
H21 H 0.0684 0.4988 0.2099 0.039 Uiso 1 1 calc R . .
C22 C 0.2339(2) 0.3334(5) 0.2770(3) 0.0259(13) Uani 1 1 d . . .
C23 C 0.2804(2) 0.4130(5) 0.3266(3) 0.0268(13) Uani 1 1 d . . .
H23 H 0.2757 0.4643 0.3580 0.032 Uiso 1 1 calc R . .
C24 C 0.3337(3) 0.4184(5) 0.3309(3) 0.0337(14) Uani 1 1 d . . .
H24 H 0.3653 0.4749 0.3645 0.040 Uiso 1 1 calc R . .
C25 C 0.3413(2) 0.3411(5) 0.2861(3) 0.0341(14) Uani 1 1 d . . .
H25 H 0.3784 0.3428 0.2900 0.041 Uiso 1 1 calc R . .
C26 C 0.2944(3) 0.2617(5) 0.2357(3) 0.0340(14) Uani 1 1 d . . .
H26 H 0.2994 0.2096 0.2047 0.041 Uiso 1 1 calc R . .
C27 C 0.2408(3) 0.2580(5) 0.2304(3) 0.0336(14) Uani 1 1 d . . .
H27 H 0.2085 0.2047 0.1953 0.040 Uiso 1 1 calc R . .
C28 C 0.1858(2) 0.1901(5) 0.3421(3) 0.0270(13) Uani 1 1 d . . .
C29 C 0.1607(2) 0.1933(5) 0.3804(3) 0.0307(14) Uani 1 1 d . . .
H29 H 0.1359 0.2661 0.3754 0.037 Uiso 1 1 calc R . .
C30 C 0.1716(2) 0.0896(5) 0.4265(3) 0.0333(14) Uani 1 1 d . . .
H30 H 0.1541 0.0909 0.4527 0.040 Uiso 1 1 calc R . .
C31 C 0.2081(2) -0.0154(5) 0.4339(3) 0.0339(14) Uani 1 1 d . . .
H31 H 0.2156 -0.0861 0.4653 0.041 Uiso 1 1 calc R . .
C32 C 0.2337(2) -0.0184(5) 0.3964(3) 0.0365(15) Uani 1 1 d . . .
H32 H 0.2591 -0.0905 0.4022 0.044 Uiso 1 1 calc R . .
C33 C 0.2225(2) 0.0842(5) 0.3497(3) 0.0300(13) Uani 1 1 d . . .
H33 H 0.2398 0.0820 0.3232 0.036 Uiso 1 1 calc R . .
N1 N -0.0459(3) 0.0737(6) 0.0182(4) 0.0367(15) Uani 1 1 d . . .
O1 O -0.02392(17) 0.2298(4) -0.05756(19) 0.0347(9) Uani 1 1 d . . .
O2 O 0.14502(16) 0.4855(3) 0.17489(19) 0.0332(9) Uani 1 1 d . . .
P1 P 0.16698(6) 0.31654(13) 0.27600(7) 0.0271(4) Uani 1 1 d . . .
 
 
_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 C2 1.401(7) . ?
C1 C15 1.404(7) . ?
C1 P1 1.807(5) . ?
C2 C3 1.369(7) . ?
C2 H2 0.9500 . ?
C3 C5 1.424(7) . ?
C3 C4 1.509(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.333(8) . ?
C5 C6 1.432(7) . ?
C6 C15 1.404(7) . ?
C6 C7 1.467(8) . ?
C7 O1 1.221(6) . ?
C7 C8 1.493(8) . ?
C8 C9 1.384(8) . ?
C8 C13 1.401(7) . ?
C9 C10 1.397(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.462(7) . ?
C14 O2 1.220(6) . ?
C14 C15 1.498(7) . ?
C16 C17 1.387(7) . ?
C16 C21 1.397(7) . ?
C16 P1 1.812(5) . ?
C17 C18 1.393(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.361(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.377(7) . ?
C22 C27 1.405(8) . ?
C22 P1 1.795(5) . ?
C23 C24 1.382(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(8) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.378(8) . ?
C28 C33 1.393(7) . ?
C28 P1 1.819(5) . ?
C29 C30 1.394(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.383(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(8) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
N1 H1B 0.62(5) . ?
N1 H1A 0.91(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
C2 C1 C15 117.6(5) . . ?
C2 C1 P1 117.4(4) . . ?
C15 C1 P1 125.0(4) . . ?
C3 C2 C1 123.3(5) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C5 119.4(5) . . ?
C2 C3 C4 121.1(5) . . ?
C5 C3 C4 119.4(5) . . ?
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 . . ?
N1 C5 C3 119.2(6) . . ?
N1 C5 C6 122.0(6) . . ?
C3 C5 C6 118.7(5) . . ?
C15 C6 C5 119.3(5) . . ?
C15 C6 C7 120.3(5) . . ?
C5 C6 C7 120.4(5) . . ?
O1 C7 C6 122.9(5) . . ?
O1 C7 C8 118.4(5) . . ?
C6 C7 C8 118.7(5) . . ?
C9 C8 C13 119.8(5) . . ?
C9 C8 C7 119.4(5) . . ?
C13 C8 C7 120.8(5) . . ?
C8 C9 C10 119.8(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.1(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.3(5) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.2(5) . . ?
C12 C13 C14 119.6(5) . . ?
C8 C13 C14 120.2(5) . . ?
O2 C14 C13 122.1(5) . . ?
O2 C14 C15 118.8(5) . . ?
C13 C14 C15 119.1(5) . . ?
C1 C15 C6 121.5(5) . . ?
C1 C15 C14 118.3(5) . . ?
C6 C15 C14 120.1(5) . . ?
C17 C16 C21 119.7(5) . . ?
C17 C16 P1 121.4(4) . . ?
C21 C16 P1 118.9(4) . . ?
C16 C17 C18 119.5(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 119.8(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 119.7(5) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C23 C22 C27 119.9(5) . . ?
C23 C22 P1 120.0(4) . . ?
C27 C22 P1 119.9(4) . . ?
C22 C23 C24 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.8(5) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 120.2(5) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 119.8(5) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 C33 120.3(5) . . ?
C29 C28 P1 120.7(4) . . ?
C33 C28 P1 118.8(4) . . ?
C28 C29 C30 119.9(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.7(5) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C30 120.7(5) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 120.0(5) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 119.5(5) . . ?
C32 C33 H33 120.3 . . ?
C28 C33 H33 120.3 . . ?
C5 N1 H1B 120(6) . . ?
C5 N1 H1A 119(5) . . ?
H1B N1 H1A 120(8) . . ?
C22 P1 C1 114.3(2) . . ?
C22 P1 C16 114.3(2) . . ?
C1 P1 C16 112.0(2) . . ?
C22 P1 C28 104.4(2) . . ?
C1 P1 C28 105.3(2) . . ?
C16 P1 C28 105.5(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              21.96
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.495
_refine_diff_density_min   -0.425
_refine_diff_density_rms    0.085
