 
data_2002src584
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C37 H27 N O4 P'
_chemical_formula_sum
 'C37 H27 N O4 P'
_chemical_formula_weight          580.57
 
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   -P1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.0140(8)
_cell_length_b                    12.3990(10)
_cell_length_c                    13.8330(14)
_cell_angle_alpha                 110.048(3)
_cell_angle_beta                  92.914(4)
_cell_angle_gamma                 113.510(3)
_cell_volume                      1444.0(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     13834
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        needle
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              606
_exptl_absorpt_coefficient_mu     0.139
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9728
_exptl_absorpt_correction_T_max   0.9917
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             9923
_diffrn_reflns_av_R_equivalents   0.0616
_diffrn_reflns_av_sigmaI/netI     0.1164
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          25.44
_reflns_number_total              5042
_reflns_number_gt                 2686
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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)+(0.1165P)²+3.7166P] 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          5042
_refine_ls_number_parameters      388
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1897
_refine_ls_R_factor_gt            0.1081
_refine_ls_wR_factor_ref          0.2989
_refine_ls_wR_factor_gt           0.2532
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_refine_ls_shift/su_max           0.017
_refine_ls_shift/su_mean          0.001
 
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 0.4111(6) 0.2898(5) 0.7797(5) 0.0413(15) Uani 1 1 d . . .
C2 C 0.4052(7) 0.3168(5) 0.6910(5) 0.0502(17) Uani 1 1 d . . .
H2 H 0.4903 0.3380 0.6607 0.060 Uiso 1 1 calc R . .
C3 C 0.2747(8) 0.3128(6) 0.6458(5) 0.0580(18) Uani 1 1 d . . .
H3 H 0.2706 0.3303 0.5843 0.070 Uiso 1 1 calc R . .
C4 C 0.1520(7) 0.2837(6) 0.6902(6) 0.0544(17) Uani 1 1 d . . .
H4 H 0.0629 0.2803 0.6590 0.065 Uiso 1 1 calc R . .
C5 C 0.1584(7) 0.2596(6) 0.7788(6) 0.0544(18) Uani 1 1 d . . .
H5 H 0.0740 0.2411 0.8099 0.065 Uiso 1 1 calc R . .
C6 C 0.2867(7) 0.2620(5) 0.8241(5) 0.0474(16) Uani 1 1 d . . .
H6 H 0.2895 0.2445 0.8857 0.057 Uiso 1 1 calc R . .
C7 C 0.7291(7) 0.4428(6) 0.8648(5) 0.0506(17) Uani 1 1 d . . .
C8 C 0.6992(8) 0.5477(7) 0.8847(6) 0.074(2) Uani 1 1 d . . .
H8 H 0.5982 0.5342 0.8762 0.089 Uiso 1 1 calc R . .
C9 C 0.8107(9) 0.6707(7) 0.9165(6) 0.075(2) Uani 1 1 d . . .
H9 H 0.7870 0.7404 0.9280 0.090 Uiso 1 1 calc R . .
C10 C 0.9540(10) 0.6904(8) 0.9309(6) 0.075(2) Uani 1 1 d . . .
H10 H 1.0320 0.7749 0.9535 0.090 Uiso 1 1 calc R . .
C11 C 0.9878(8) 0.5903(10) 0.9134(7) 0.088(3) Uani 1 1 d . . .
H11 H 1.0894 0.6060 0.9246 0.106 Uiso 1 1 calc R . .
C12 C 0.8750(7) 0.4641(8) 0.8792(6) 0.070(2) Uani 1 1 d . . .
H12 H 0.8997 0.3947 0.8662 0.084 Uiso 1 1 calc R . .
C13 C 0.5542(7) 0.2642(6) 0.9539(5) 0.0476(16) Uani 1 1 d . . .
C14 C 0.6129(7) 0.3656(6) 1.0507(5) 0.0526(17) Uani 1 1 d . . .
H14 H 0.6719 0.4497 1.0548 0.063 Uiso 1 1 calc R . .
C15 C 0.5865(8) 0.3460(7) 1.1421(6) 0.0623(19) Uani 1 1 d . . .
H15 H 0.6280 0.4163 1.2087 0.075 Uiso 1 1 calc R . .
C16 C 0.5005(8) 0.2251(8) 1.1364(6) 0.0637(19) Uani 1 1 d . . .
H16 H 0.4808 0.2119 1.1989 0.076 Uiso 1 1 calc R . .
C17 C 0.4432(10) 0.1238(8) 1.0412(7) 0.078(2) Uani 1 1 d . . .
H17 H 0.3847 0.0400 1.0377 0.094 Uiso 1 1 calc R . .
C18 C 0.4698(9) 0.1422(7) 0.9495(7) 0.077(2) Uani 1 1 d . . .
H18 H 0.4301 0.0710 0.8834 0.092 Uiso 1 1 calc R . .
C19 C 0.5873(7) 0.1523(6) 0.7377(5) 0.0585(19) Uani 1 1 d . . .
C20 C 0.4801(11) 0.0691(8) 0.6416(7) 0.117(4) Uani 1 1 d . . .
H20 H 0.4151 0.0967 0.6161 0.140 Uiso 1 1 calc R . .
C21 C 0.4688(7) -0.0480(5) 0.5859(4) 0.0455(15) Uani 1 1 d . . .
C22 C 0.3385(12) -0.1429(7) 0.5039(7) 0.104(4) Uani 1 1 d . . .
C23 C 0.3190(8) -0.2765(6) 0.4755(5) 0.0552(18) Uani 1 1 d . . .
C24 C 0.2025(8) -0.3791(7) 0.3926(6) 0.068(2) Uani 1 1 d . . .
H24 H 0.1410 -0.3623 0.3509 0.082 Uiso 1 1 calc R . .
C25 C 0.1767(9) -0.5022(7) 0.3714(6) 0.073(2) Uani 1 1 d . . .
H25 H 0.1003 -0.5711 0.3135 0.088 Uiso 1 1 calc R . .
C26 C 0.2633(12) -0.5257(7) 0.4353(7) 0.099(3) Uani 1 1 d . . .
H26 H 0.2444 -0.6113 0.4226 0.119 Uiso 1 1 calc R . .
C27 C 0.3767(11) -0.4255(7) 0.5170(6) 0.088(3) Uani 1 1 d . . .
H27 H 0.4346 -0.4425 0.5611 0.105 Uiso 1 1 calc R . .
C28 C 0.4071(7) -0.3014(5) 0.5352(5) 0.0439(15) Uani 1 1 d . . .
C29 C 0.5777(8) -0.0838(6) 0.6136(6) 0.0591(19) Uani 1 1 d . . .
C30 C 0.6994(7) 0.1210(6) 0.7704(5) 0.0480(16) Uani 1 1 d . . .
C31 C 0.8166(7) -0.0258(5) 0.7213(6) 0.0517(17) Uani 1 1 d . . .
C32 C 0.8889(8) -0.0553(7) 0.6434(8) 0.085(3) Uani 1 1 d . . .
H32 H 0.8674 -0.0507 0.5776 0.102 Uiso 1 1 calc R . .
C33 C 1.0117(9) -0.0978(6) 0.6691(7) 0.080(3) Uani 1 1 d . . .
H33 H 1.0699 -0.1207 0.6212 0.095 Uiso 1 1 calc R . .
C34 C 1.0239(11) -0.0976(7) 0.7664(7) 0.079(2) Uani 1 1 d . . .
C35 C 0.9687(12) -0.0584(10) 0.8434(9) 0.102(3) Uani 1 1 d . . .
H35 H 1.0005 -0.0508 0.9123 0.122 Uiso 1 1 calc R . .
C36 C 0.8586(9) -0.0280(8) 0.8177(8) 0.085(3) Uani 1 1 d . . .
H36 H 0.8059 -0.0065 0.8706 0.102 Uiso 1 1 calc R . .
C37 C 1.1956(9) -0.1892(10) 0.7164(8) 0.110(4) Uani 1 1 d . . .
H37A H 1.1363 -0.2823 0.6816 0.164 Uiso 1 1 calc R . .
H37B H 1.2986 -0.1692 0.7438 0.164 Uiso 1 1 calc R . .
H37C H 1.1946 -0.1505 0.6655 0.164 Uiso 1 1 calc R . .
N1 N 0.6961(5) 0.0051(4) 0.7034(4) 0.0416(12) Uani 1 1 d . . .
O1 O 0.2357(5) -0.1213(4) 0.4736(3) 0.0633(13) Uani 1 1 d . . .
O2 O 0.5243(5) -0.2070(4) 0.6161(3) 0.0506(11) Uani 1 1 d . . .
O4 O 0.7964(5) 0.1883(4) 0.8539(3) 0.0589(13) Uani 1 1 d . . .
O3 O 1.1383(9) -0.1429(8) 0.7948(7) 0.134(3) Uani 1 1 d . . .
P1 P 0.57688(18) 0.28404(15) 0.83092(13) 0.0487(5) 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 C2 1.383(9) . ?
C1 C6 1.388(8) . ?
C1 P1 1.809(6) . ?
C2 C3 1.395(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.368(9) . ?
C7 C8 1.390(10) . ?
C7 P1 1.821(6) . ?
C8 C9 1.378(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.347(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.361(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.406(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.376(8) . ?
C13 C18 1.385(10) . ?
C13 P1 1.814(7) . ?
C14 C15 1.387(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.362(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(11) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.420(9) . ?
C19 C30 1.425(9) . ?
C19 P1 1.745(6) . ?
C20 C21 1.344(10) . ?
C20 H20 0.9500 . ?
C21 C29 1.412(9) . ?
C21 C22 1.443(9) . ?
C22 O1 1.249(9) . ?
C22 C23 1.491(10) . ?
C23 C28 1.368(9) . ?
C23 C24 1.406(9) . ?
C24 C25 1.362(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.370(9) . ?
C27 H27 0.9500 . ?
C28 O2 1.368(7) . ?
C29 O2 1.417(7) . ?
C29 N1 1.426(8) . ?
C30 O4 1.245(7) . ?
C30 N1 1.404(7) . ?
C31 C32 1.356(10) . ?
C31 C36 1.391(11) . ?
C31 N1 1.438(8) . ?
C32 C33 1.586(13) . ?
C32 H32 0.9500 . ?
C33 C34 1.345(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.263(13) . ?
C34 O3 1.550(12) . ?
C35 C36 1.366(12) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 O3 1.317(11) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
 
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 C6 118.9(6) . . ?
C2 C1 P1 119.2(5) . . ?
C6 C1 P1 121.9(5) . . ?
C1 C2 C3 120.1(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.2(6) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 118.1(6) . . ?
C12 C7 P1 121.6(6) . . ?
C8 C7 P1 120.1(5) . . ?
C9 C8 C7 122.3(7) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C10 C9 C8 118.9(9) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.5(8) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 121.1(7) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 119.0(8) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C18 119.0(7) . . ?
C14 C13 P1 122.7(5) . . ?
C18 C13 P1 118.2(5) . . ?
C13 C14 C15 120.4(7) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.0(7) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.0(8) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.5(8) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.1(7) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C30 120.5(6) . . ?
C20 C19 P1 123.5(5) . . ?
C30 C19 P1 115.4(4) . . ?
C21 C20 C19 121.3(7) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C29 120.2(6) . . ?
C20 C21 C22 120.6(7) . . ?
C29 C21 C22 118.8(6) . . ?
O1 C22 C21 124.0(6) . . ?
O1 C22 C23 121.2(7) . . ?
C21 C22 C23 113.5(6) . . ?
C28 C23 C24 119.3(6) . . ?
C28 C23 C22 120.2(6) . . ?
C24 C23 C22 120.3(6) . . ?
C25 C24 C23 120.7(7) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.1(7) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C27 C26 C25 120.3(7) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.6(8) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
O2 C28 C23 123.0(5) . . ?
O2 C28 C27 117.1(6) . . ?
C23 C28 C27 119.9(6) . . ?
C21 C29 O2 116.5(6) . . ?
C21 C29 N1 118.5(6) . . ?
O2 C29 N1 108.7(5) . . ?
O4 C30 N1 119.1(6) . . ?
O4 C30 C19 124.3(6) . . ?
N1 C30 C19 116.5(5) . . ?
C32 C31 C36 119.3(8) . . ?
C32 C31 N1 120.2(7) . . ?
C36 C31 N1 120.5(7) . . ?
C31 C32 C33 115.8(9) . . ?
C31 C32 H32 122.1 . . ?
C33 C32 H32 122.1 . . ?
C34 C33 C32 112.3(8) . . ?
C34 C33 H33 123.9 . . ?
C32 C33 H33 123.9 . . ?
C35 C34 C33 132.6(10) . . ?
C35 C34 O3 112.4(9) . . ?
C33 C34 O3 114.8(9) . . ?
C34 C35 C36 113.3(10) . . ?
C34 C35 H35 123.4 . . ?
C36 C35 H35 123.4 . . ?
C35 C36 C31 126.0(10) . . ?
C35 C36 H36 117.0 . . ?
C31 C36 H36 117.0 . . ?
O3 C37 H37A 109.5 . . ?
O3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C30 N1 C29 122.0(5) . . ?
C30 N1 C31 120.6(5) . . ?
C29 N1 C31 117.4(5) . . ?
C28 O2 C29 114.8(5) . . ?
C37 O3 C34 115.1(9) . . ?
C19 P1 C1 107.1(3) . . ?
C19 P1 C13 111.0(3) . . ?
C1 P1 C13 107.2(3) . . ?
C19 P1 C7 118.5(3) . . ?
C1 P1 C7 105.9(3) . . ?
C13 P1 C7 106.5(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.947
_diffrn_reflns_theta_full              25.44
_diffrn_measured_fraction_theta_full   0.947
_refine_diff_density_max    1.062
_refine_diff_density_min   -0.430
_refine_diff_density_rms    0.076
