data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. Gabbutt
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C32 H26 N O4 P'
_chemical_formula_sum
 'C32 H26 N O4 P'
_chemical_formula_weight          519.51
 
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            Monoclinic
_symmetry_space_group_name_H-M    Cc
_symmetry_space_group_name_hall   C-2yc
 
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'
 
_cell_length_a                    13.4334(2)
_cell_length_b                    14.3903(2)
_cell_length_c                    13.7137(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.4070(10)
_cell_angle_gamma                 90.00
_cell_volume                      2650.94(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3145
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.302
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1088
_exptl_absorpt_coefficient_mu     0.142
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9653
_exptl_absorpt_correction_T_max   0.9803
_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             22956
_diffrn_reflns_av_R_equivalents   0.0463
_diffrn_reflns_av_sigmaI/netI     0.0484
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.20
_diffrn_reflns_theta_max          27.49
_reflns_number_total              6014
_reflns_number_gt                 5700
_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)+(0.0257P)²+1.3820P] 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        0.0063(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.02(6)
_refine_ls_number_reflns          6014
_refine_ls_number_parameters      346
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0369
_refine_ls_R_factor_gt            0.0333
_refine_ls_wR_factor_ref          0.0758
_refine_ls_wR_factor_gt           0.0735
_refine_ls_goodness_of_fit_ref    1.014
_refine_ls_restrained_S_all       1.014
_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 0.92211(12) 0.57630(11) 0.14950(12) 0.0189(3) Uani 1 1 d . . .
C2 C 0.96756(14) 0.52458(12) 0.07613(13) 0.0253(4) Uani 1 1 d . . .
H2 H 0.9401 0.5243 0.0121 0.030 Uiso 1 1 calc R . .
C3 C 1.05221(14) 0.47385(13) 0.09638(13) 0.0278(4) Uani 1 1 d . . .
H3 H 1.0833 0.4395 0.0459 0.033 Uiso 1 1 calc R . .
C4 C 1.09247(14) 0.47252(12) 0.18986(14) 0.0270(4) Uani 1 1 d . . .
H4 H 1.1490 0.4351 0.2040 0.032 Uiso 1 1 calc R . .
C5 C 1.04975(13) 0.52608(11) 0.26250(12) 0.0218(3) Uani 1 1 d . . .
H5 H 1.0777 0.5252 0.3263 0.026 Uiso 1 1 calc R . .
C6 C 0.96601(12) 0.58143(11) 0.24319(11) 0.0173(3) Uani 1 1 d . . .
C7 C 0.92171(12) 0.64539(11) 0.31644(11) 0.0172(3) Uani 1 1 d . . .
C8 C 0.98120(12) 0.69039(11) 0.39111(11) 0.0169(3) Uani 1 1 d . . .
C9 C 1.08760(12) 0.68724(11) 0.39090(12) 0.0184(3) Uani 1 1 d . . .
C10 C 0.93053(12) 0.73388(11) 0.46809(11) 0.0167(3) Uani 1 1 d . . .
H10 H 0.8625 0.7170 0.4743 0.020 Uiso 1 1 calc R . .
C11 C 0.96490(12) 0.79794(11) 0.53654(11) 0.0168(3) Uani 1 1 d . . .
C12 C 1.04919(12) 0.86190(11) 0.52593(12) 0.0187(3) Uani 1 1 d . . .
C13 C 1.16862(14) 0.92794(13) 0.41807(13) 0.0277(4) Uani 1 1 d . . .
H13A H 1.2107 0.9004 0.3666 0.033 Uiso 1 1 calc R . .
H13B H 1.2088 0.9320 0.4787 0.033 Uiso 1 1 calc R . .
C14 C 1.13567(16) 1.02359(14) 0.38761(16) 0.0356(5) Uani 1 1 d . . .
H14A H 1.0949 1.0192 0.3282 0.053 Uiso 1 1 calc R . .
H14B H 1.1942 1.0622 0.3749 0.053 Uiso 1 1 calc R . .
H14C H 1.0964 1.0517 0.4398 0.053 Uiso 1 1 calc R . .
C15 C 0.96783(12) 0.77703(11) 0.75340(11) 0.0170(3) Uani 1 1 d . . .
C16 C 1.06995(13) 0.76156(12) 0.75258(12) 0.0214(3) Uani 1 1 d . . .
H16 H 1.1075 0.7756 0.6960 0.026 Uiso 1 1 calc R . .
C17 C 1.11701(13) 0.72539(13) 0.83484(13) 0.0253(4) Uani 1 1 d . . .
H17 H 1.1868 0.7147 0.8345 0.030 Uiso 1 1 calc R . .
C18 C 1.06227(14) 0.70501(13) 0.91722(13) 0.0273(4) Uani 1 1 d . . .
H18 H 1.0945 0.6792 0.9728 0.033 Uiso 1 1 calc R . .
C19 C 0.96083(14) 0.72189(14) 0.91920(13) 0.0295(4) Uani 1 1 d . . .
H19 H 0.9241 0.7089 0.9765 0.035 Uiso 1 1 calc R . .
C20 C 0.91271(13) 0.75785(12) 0.83743(12) 0.0232(4) Uani 1 1 d . . .
H20 H 0.8431 0.7693 0.8385 0.028 Uiso 1 1 calc R . .
C21 C 0.86998(12) 0.93819(11) 0.65812(12) 0.0180(3) Uani 1 1 d . . .
C22 C 0.88282(13) 0.98597(12) 0.74623(13) 0.0232(4) Uani 1 1 d . . .
H22 H 0.9014 0.9532 0.8037 0.028 Uiso 1 1 calc R . .
C23 C 0.86834(14) 1.08157(13) 0.74935(15) 0.0294(4) Uani 1 1 d . . .
H23 H 0.8772 1.1143 0.8089 0.035 Uiso 1 1 calc R . .
C24 C 0.84092(14) 1.12898(13) 0.66535(16) 0.0312(4) Uani 1 1 d . . .
H24 H 0.8319 1.1944 0.6677 0.037 Uiso 1 1 calc R . .
C25 C 0.82647(14) 1.08231(12) 0.57814(14) 0.0287(4) Uani 1 1 d . . .
H25 H 0.8064 1.1153 0.5213 0.034 Uiso 1 1 calc R . .
C26 C 0.84155(13) 0.98689(12) 0.57440(13) 0.0239(4) Uani 1 1 d . . .
H26 H 0.8325 0.9546 0.5146 0.029 Uiso 1 1 calc R . .
C27 C 0.78839(12) 0.74703(11) 0.64638(11) 0.0151(3) Uani 1 1 d . . .
C28 C 0.69327(12) 0.78530(11) 0.64916(11) 0.0188(3) Uani 1 1 d . . .
H28 H 0.6848 0.8508 0.6499 0.023 Uiso 1 1 calc R . .
C29 C 0.61077(13) 0.72703(12) 0.65080(13) 0.0213(3) Uani 1 1 d . . .
H29 H 0.5459 0.7531 0.6529 0.026 Uiso 1 1 calc R . .
C30 C 0.62211(13) 0.63149(12) 0.64935(12) 0.0210(3) Uani 1 1 d . . .
H30 H 0.5651 0.5924 0.6496 0.025 Uiso 1 1 calc R . .
C31 C 0.71686(13) 0.59264(11) 0.64753(12) 0.0217(3) Uani 1 1 d . . .
H31 H 0.7246 0.5270 0.6463 0.026 Uiso 1 1 calc R . .
C32 C 0.79990(12) 0.64960(12) 0.64744(12) 0.0200(3) Uani 1 1 d . . .
H32 H 0.8647 0.6231 0.6481 0.024 Uiso 1 1 calc R . .
N1 N 1.17315(11) 0.68153(12) 0.39525(11) 0.0281(3) Uani 1 1 d . . .
O1 O 0.83673(9) 0.62178(9) 0.12722(9) 0.0251(3) Uani 1 1 d . . .
H1 H 0.8072 0.6362 0.1789 0.038 Uiso 1 1 calc R . .
O2 O 0.83112(8) 0.66421(9) 0.30933(8) 0.0228(3) Uani 1 1 d . . .
O3 O 1.08144(9) 0.90847(8) 0.59356(8) 0.0237(3) Uani 1 1 d . . .
O4 O 1.08177(9) 0.86896(9) 0.43440(8) 0.0256(3) Uani 1 1 d . . .
P1 P 0.89965(3) 0.81637(3) 0.64719(3) 0.01490(9) 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 1.354(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.412(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.490(2) . ?
C7 O2 1.250(2) . ?
C7 C8 1.447(2) . ?
C8 C10 1.407(2) . ?
C8 C9 1.430(2) . ?
C9 N1 1.153(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.467(2) . ?
C11 P1 1.7777(15) . ?
C12 O3 1.221(2) . ?
C12 O4 1.3362(19) . ?
C13 O4 1.461(2) . ?
C13 C14 1.504(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.390(2) . ?
C15 C20 1.402(2) . ?
C15 P1 1.8061(16) . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.396(2) . ?
C21 C22 1.400(2) . ?
C21 P1 1.8042(16) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.392(2) . ?
C27 C32 1.411(2) . ?
C27 P1 1.7970(16) . ?
C28 C29 1.390(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(2) . ?
C31 H31 0.9500 . ?
C32 H32 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 C2 117.99(15) . . ?
O1 C1 C6 121.87(14) . . ?
C2 C1 C6 120.13(15) . . ?
C3 C2 C1 120.12(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.60(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.69(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.03(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.13(14) . . ?
C5 C6 C7 123.19(15) . . ?
C1 C6 C7 118.67(14) . . ?
O2 C7 C8 119.38(14) . . ?
O2 C7 C6 118.34(14) . . ?
C8 C7 C6 122.17(14) . . ?
C10 C8 C9 120.30(14) . . ?
C10 C8 C7 117.53(14) . . ?
C9 C8 C7 122.09(14) . . ?
N1 C9 C8 176.18(18) . . ?
C11 C10 C8 129.83(15) . . ?
C11 C10 H10 115.1 . . ?
C8 C10 H10 115.1 . . ?
C10 C11 C12 126.94(14) . . ?
C10 C11 P1 120.75(12) . . ?
C12 C11 P1 112.12(11) . . ?
O3 C12 O4 123.70(15) . . ?
O3 C12 C11 122.61(14) . . ?
O4 C12 C11 113.52(13) . . ?
O4 C13 C14 109.90(15) . . ?
O4 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O4 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.16(15) . . ?
C16 C15 P1 122.59(12) . . ?
C20 C15 P1 117.19(12) . . ?
C15 C16 C17 119.77(15) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.04(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.50(17) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.10(16) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 119.41(16) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
C26 C21 C22 119.64(16) . . ?
C26 C21 P1 118.61(13) . . ?
C22 C21 P1 121.54(13) . . ?
C23 C22 C21 119.76(17) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 119.85(17) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.93(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 119.47(17) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C21 120.34(17) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C28 C27 C32 119.56(15) . . ?
C28 C27 P1 122.93(12) . . ?
C32 C27 P1 117.44(12) . . ?
C29 C28 C27 119.60(15) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 120.75(16) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.05(16) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 119.97(15) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.03(15) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C1 O1 H1 109.5 . . ?
C12 O4 C13 117.09(13) . . ?
C11 P1 C27 109.08(7) . . ?
C11 P1 C21 109.05(7) . . ?
C27 P1 C21 110.84(7) . . ?
C11 P1 C15 113.04(8) . . ?
C27 P1 C15 104.35(7) . . ?
C21 P1 C15 110.40(7) . . ?
 
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 1.86 2.5726(17) 141.8 .
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.189
_refine_diff_density_min   -0.191
_refine_diff_density_rms    0.037
