data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. D. Gabbutt
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C30 H21 N2 O2 P'
_chemical_formula_sum
 'C30 H21 N2 O2 P'
_chemical_formula_weight          472.46
 
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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.3901(2)
_cell_length_b                    11.5292(3)
_cell_length_c                    12.0700(3)
_cell_angle_alpha                 67.7260(10)
_cell_angle_beta                  72.1360(10)
_cell_angle_gamma                 63.5460(10)
_cell_volume                      1181.17(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5227
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.328
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              492
_exptl_absorpt_coefficient_mu     0.148
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9543
_exptl_absorpt_correction_T_max   0.9768
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             23837
_diffrn_reflns_av_R_equivalents   0.0396
_diffrn_reflns_av_sigmaI/netI     0.0392
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.12
_diffrn_reflns_theta_max          27.49
_reflns_number_total              5389
_reflns_number_gt                 4302
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0375P)²+0.4347P] 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      SHELXL
_refine_ls_extinction_coef        0.016(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5389
_refine_ls_number_parameters      318
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0539
_refine_ls_R_factor_gt            0.0378
_refine_ls_wR_factor_ref          0.0921
_refine_ls_wR_factor_gt           0.0851
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_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
C1 C 0.45672(17) 0.34670(16) 0.09231(14) 0.0278(3) Uani 1 1 d . . .
C2 C 0.45129(15) 0.39994(15) 0.18254(13) 0.0239(3) Uani 1 1 d . . .
C3 C 0.55091(16) 0.32038(15) 0.26377(15) 0.0281(3) Uani 1 1 d . . .
H3 H 0.5451 0.3518 0.3281 0.034 Uiso 1 1 calc R . .
C4 C 0.65708(17) 0.19754(16) 0.25241(16) 0.0338(4) Uani 1 1 d . . .
H4 H 0.7233 0.1447 0.3085 0.041 Uiso 1 1 calc R . .
C5 C 0.66598(18) 0.15195(17) 0.15767(17) 0.0366(4) Uani 1 1 d . . .
H5 H 0.7416 0.0694 0.1472 0.044 Uiso 1 1 calc R . .
C6 C 0.56692(18) 0.22475(17) 0.07927(15) 0.0339(4) Uani 1 1 d . . .
H6 H 0.5737 0.1917 0.0158 0.041 Uiso 1 1 calc R . .
C7 C 0.33650(15) 0.53234(15) 0.19113(13) 0.0233(3) Uani 1 1 d . . .
C8 C 0.35052(14) 0.61628(14) 0.24878(12) 0.0210(3) Uani 1 1 d . . .
C9 C 0.48320(14) 0.61310(14) 0.25425(12) 0.0201(3) Uani 1 1 d . . .
H9 H 0.5658 0.5451 0.2248 0.024 Uiso 1 1 calc R . .
C10 C 0.51642(14) 0.69314(14) 0.29583(12) 0.0196(3) Uani 1 1 d . . .
C11 C 0.21411(15) 0.71602(14) 0.28376(12) 0.0218(3) Uani 1 1 d . . .
C12 C 0.41016(15) 0.80495(15) 0.33791(13) 0.0219(3) Uani 1 1 d . . .
C13 C 0.81034(14) 0.49574(14) 0.28501(12) 0.0195(3) Uani 1 1 d . . .
C14 C 0.92009(15) 0.46432(15) 0.18748(13) 0.0236(3) Uani 1 1 d . . .
H14 H 0.9369 0.5345 0.1187 0.028 Uiso 1 1 calc R . .
C15 C 1.00452(16) 0.33028(15) 0.19132(14) 0.0275(3) Uani 1 1 d . . .
H15 H 1.0785 0.3087 0.1246 0.033 Uiso 1 1 calc R . .
C16 C 0.98136(16) 0.22774(15) 0.29200(14) 0.0264(3) Uani 1 1 d . . .
H16 H 1.0399 0.1361 0.2942 0.032 Uiso 1 1 calc R . .
C17 C 0.87313(16) 0.25802(15) 0.38965(13) 0.0254(3) Uani 1 1 d . . .
H17 H 0.8585 0.1873 0.4590 0.030 Uiso 1 1 calc R . .
C18 C 0.78652(15) 0.39132(15) 0.38596(13) 0.0239(3) Uani 1 1 d . . .
H18 H 0.7108 0.4121 0.4519 0.029 Uiso 1 1 calc R . .
C19 C 0.72495(14) 0.70801(14) 0.40330(12) 0.0202(3) Uani 1 1 d . . .
C20 C 0.66339(15) 0.84359(15) 0.40249(13) 0.0246(3) Uani 1 1 d . . .
H20 H 0.6099 0.9106 0.3403 0.030 Uiso 1 1 calc R . .
C21 C 0.68039(16) 0.88013(16) 0.49233(14) 0.0285(3) Uani 1 1 d . . .
H21 H 0.6375 0.9721 0.4924 0.034 Uiso 1 1 calc R . .
C22 C 0.75982(16) 0.78283(17) 0.58196(14) 0.0296(3) Uani 1 1 d . . .
H22 H 0.7700 0.8081 0.6442 0.036 Uiso 1 1 calc R . .
C23 C 0.82446(16) 0.64900(16) 0.58161(13) 0.0277(3) Uani 1 1 d . . .
H23 H 0.8811 0.5832 0.6422 0.033 Uiso 1 1 calc R . .
C24 C 0.80698(15) 0.61038(15) 0.49306(13) 0.0235(3) Uani 1 1 d . . .
H24 H 0.8504 0.5182 0.4934 0.028 Uiso 1 1 calc R . .
C25 C 0.76280(14) 0.77615(13) 0.14538(12) 0.0187(3) Uani 1 1 d . . .
C26 C 0.68186(16) 0.85107(15) 0.05184(13) 0.0252(3) Uani 1 1 d . . .
H26 H 0.5900 0.8471 0.0597 0.030 Uiso 1 1 calc R . .
C27 C 0.73629(18) 0.93215(15) -0.05370(14) 0.0321(4) Uani 1 1 d . . .
H27 H 0.6807 0.9849 -0.1176 0.038 Uiso 1 1 calc R . .
C28 C 0.87107(18) 0.93591(15) -0.06547(14) 0.0325(4) Uani 1 1 d . . .
H28 H 0.9077 0.9915 -0.1375 0.039 Uiso 1 1 calc R . .
C29 C 0.95311(17) 0.85924(16) 0.02695(14) 0.0298(3) Uani 1 1 d . . .
H29 H 1.0466 0.8607 0.0174 0.036 Uiso 1 1 calc R . .
C30 C 0.89914(15) 0.78070(14) 0.13288(13) 0.0237(3) Uani 1 1 d . . .
H30 H 0.9543 0.7299 0.1971 0.028 Uiso 1 1 calc R . .
N1 N 0.10233(13) 0.79253(14) 0.31298(12) 0.0302(3) Uani 1 1 d . . .
N2 N 0.32883(14) 0.89842(14) 0.37023(13) 0.0317(3) Uani 1 1 d . . .
O1 O 0.35726(13) 0.41068(12) 0.01645(10) 0.0352(3) Uani 1 1 d . . .
H1 H 0.2891 0.4757 0.0396 0.053 Uiso 1 1 calc R . .
O2 O 0.22387(11) 0.57440(11) 0.14776(10) 0.0302(3) Uani 1 1 d . . .
P1 P 0.70019(4) 0.66805(3) 0.28297(3) 0.01786(10) 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 O1 1.3564(19) . ?
C1 C6 1.391(2) . ?
C1 C2 1.416(2) . ?
C2 C3 1.403(2) . ?
C2 C7 1.478(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.2476(17) . ?
C7 C8 1.463(2) . ?
C8 C9 1.3839(19) . ?
C8 C11 1.4347(19) . ?
C9 C10 1.401(2) . ?
C9 H9 0.9500 . ?
C10 C12 1.4222(19) . ?
C10 P1 1.7646(13) . ?
C11 N1 1.1502(19) . ?
C12 N2 1.1544(19) . ?
C13 C14 1.396(2) . ?
C13 C18 1.401(2) . ?
C13 P1 1.7920(14) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.398(2) . ?
C19 C24 1.3981(19) . ?
C19 P1 1.7972(14) . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.3871(19) . ?
C25 C30 1.4005(19) . ?
C25 P1 1.7958(14) . ?
C26 C27 1.394(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
O1 H1 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
O1 C1 C6 117.81(14) . . ?
O1 C1 C2 122.27(14) . . ?
C6 C1 C2 119.92(15) . . ?
C3 C2 C1 117.94(14) . . ?
C3 C2 C7 123.22(13) . . ?
C1 C2 C7 118.75(13) . . ?
C4 C3 C2 121.52(15) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.17(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.84(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.35(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O2 C7 C8 118.67(13) . . ?
O2 C7 C2 119.16(13) . . ?
C8 C7 C2 122.16(12) . . ?
C9 C8 C11 122.48(13) . . ?
C9 C8 C7 123.42(12) . . ?
C11 C8 C7 113.54(12) . . ?
C8 C9 C10 130.97(13) . . ?
C8 C9 H9 114.5 . . ?
C10 C9 H9 114.5 . . ?
C9 C10 C12 124.00(12) . . ?
C9 C10 P1 119.64(10) . . ?
C12 C10 P1 116.06(10) . . ?
N1 C11 C8 177.44(15) . . ?
N2 C12 C10 176.75(15) . . ?
C14 C13 C18 119.61(13) . . ?
C14 C13 P1 120.78(11) . . ?
C18 C13 P1 119.61(11) . . ?
C15 C14 C13 119.78(13) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.24(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.38(14) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.90(13) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.07(13) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C24 119.76(13) . . ?
C20 C19 P1 117.56(10) . . ?
C24 C19 P1 122.64(11) . . ?
C21 C20 C19 119.95(14) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.03(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.43(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.27(14) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 119.53(14) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C26 C25 C30 120.09(13) . . ?
C26 C25 P1 121.83(11) . . ?
C30 C25 P1 118.06(10) . . ?
C25 C26 C27 119.54(14) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.04(14) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.46(14) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.06(14) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C25 119.80(14) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
C1 O1 H1 109.5 . . ?
C10 P1 C13 108.30(6) . . ?
C10 P1 C25 112.66(6) . . ?
C13 P1 C25 108.64(6) . . ?
C10 P1 C19 111.13(6) . . ?
C13 P1 C19 111.02(6) . . ?
C25 P1 C19 105.07(6) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1 H1 O2  0.84 1.83 2.5662(16) 145.1 .
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.272
_refine_diff_density_min   -0.322
_refine_diff_density_rms    0.045
