data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H61 Cl N9 O P3'
_chemical_formula_weight          620.18
 
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'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 
_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                    33.651(7)
_cell_length_b                    11.506(2)
_cell_length_c                    19.895(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  107.44(3)
_cell_angle_gamma                 90.00
_cell_volume                      7349(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     44841
_cell_measurement_theta_min       1.0
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.121
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2704
_exptl_absorpt_coefficient_mu     0.265
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9368
_exptl_absorpt_correction_T_max   0.9614
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(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        '\\f and \\w 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             48779
_diffrn_reflns_av_R_equivalents   0.0929
_diffrn_reflns_av_sigmaI/netI     0.0684
_diffrn_reflns_limit_h_min        -43
_diffrn_reflns_limit_h_max        43
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          2.07
_diffrn_reflns_theta_max          27.46
_reflns_number_total              8329
_reflns_number_gt                 5473
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.1190P)²+10.4914P] 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        0.0003(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          8329
_refine_ls_number_parameters      380
_refine_ls_number_restraints      12
_refine_ls_R_factor_all           0.1091
_refine_ls_R_factor_gt            0.0654
_refine_ls_wR_factor_ref          0.2083
_refine_ls_wR_factor_gt           0.1799
_refine_ls_goodness_of_fit_ref    0.990
_refine_ls_restrained_S_all       0.989
_refine_ls_shift/su_max           0.063
_refine_ls_shift/su_mean          0.004
 
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 0.18765(10) 0.5097(3) 0.17305(16) 0.0450(8) Uani 1 1 d . . .
C2 C 0.19565(15) 0.5642(5) 0.2465(2) 0.0761(14) Uani 1 1 d . . .
H2A H 0.2017 0.5026 0.2822 0.114 Uiso 1 1 calc R . .
H2B H 0.1709 0.6074 0.2483 0.114 Uiso 1 1 calc R . .
H2C H 0.2195 0.6172 0.2558 0.114 Uiso 1 1 calc R . .
C3 C 0.22528(11) 0.4387(4) 0.1722(2) 0.0650(12) Uani 1 1 d . . .
H3A H 0.2205 0.4035 0.1256 0.097 Uiso 1 1 calc R . .
H3B H 0.2299 0.3774 0.2079 0.097 Uiso 1 1 calc R . .
H3C H 0.2498 0.4892 0.1826 0.097 Uiso 1 1 calc R . .
C4 C 0.14932(11) 0.4329(4) 0.1593(2) 0.0561(10) Uani 1 1 d . . .
H4A H 0.1252 0.4804 0.1598 0.084 Uiso 1 1 calc R . .
H4B H 0.1541 0.3733 0.1960 0.084 Uiso 1 1 calc R . .
H4C H 0.1439 0.3955 0.1132 0.084 Uiso 1 1 calc R . .
C5 C 0.13282(10) 0.4567(3) -0.06924(16) 0.0399(7) Uani 1 1 d . . .
C6 C 0.16095(12) 0.3686(4) -0.0896(2) 0.0550(10) Uani 1 1 d . . .
H6A H 0.1857 0.4081 -0.0947 0.082 Uiso 1 1 calc R . .
H6B H 0.1458 0.3318 -0.1343 0.082 Uiso 1 1 calc R . .
H6C H 0.1695 0.3091 -0.0528 0.082 Uiso 1 1 calc R . .
C7 C 0.09493(11) 0.3952(3) -0.0604(2) 0.0527(9) Uani 1 1 d . . .
H7A H 0.1039 0.3330 -0.0254 0.079 Uiso 1 1 calc R . .
H7B H 0.0787 0.3618 -0.1056 0.079 Uiso 1 1 calc R . .
H7C H 0.0777 0.4510 -0.0444 0.079 Uiso 1 1 calc R . .
C8 C 0.12078(13) 0.5521(4) -0.12501(18) 0.0578(10) Uani 1 1 d . . .
H8A H 0.1063 0.6147 -0.1084 0.087 Uiso 1 1 calc R . .
H8B H 0.1023 0.5198 -0.1689 0.087 Uiso 1 1 calc R . .
H8C H 0.1459 0.5831 -0.1336 0.087 Uiso 1 1 calc R . .
C9 C 0.04266(10) 0.7371(3) 0.13476(17) 0.0415(8) Uani 1 1 d . . .
C10 C 0.07873(13) 0.7121(4) 0.2006(2) 0.0672(12) Uani 1 1 d . . .
H10A H 0.0680 0.6761 0.2364 0.101 Uiso 1 1 calc R . .
H10B H 0.0929 0.7849 0.2191 0.101 Uiso 1 1 calc R . .
H10C H 0.0984 0.6590 0.1888 0.101 Uiso 1 1 calc R . .
C11 C 0.02131(14) 0.6246(4) 0.1048(2) 0.0664(12) Uani 1 1 d . . .
H11A H 0.0122 0.5841 0.1409 0.100 Uiso 1 1 calc R . .
H11B H 0.0409 0.5751 0.0899 0.100 Uiso 1 1 calc R . .
H11C H -0.0029 0.6415 0.0642 0.100 Uiso 1 1 calc R . .
C12 C 0.01163(14) 0.8186(4) 0.1535(2) 0.0677(12) Uani 1 1 d . . .
H12A H -0.0114 0.8358 0.1110 0.102 Uiso 1 1 calc R . .
H12B H 0.0257 0.8910 0.1731 0.102 Uiso 1 1 calc R . .
H12C H 0.0007 0.7811 0.1885 0.102 Uiso 1 1 calc R . .
C13 C -0.00197(9) 0.7668(3) -0.09142(17) 0.0404(8) Uani 1 1 d . . .
C14 C -0.04212(10) 0.6967(4) -0.1068(3) 0.0680(12) Uani 1 1 d . . .
H14A H -0.0387 0.6229 -0.1290 0.102 Uiso 1 1 calc R . .
H14B H -0.0650 0.7409 -0.1387 0.102 Uiso 1 1 calc R . .
H14C H -0.0485 0.6814 -0.0627 0.102 Uiso 1 1 calc R . .
C15 C -0.00787(11) 0.8834(3) -0.0607(2) 0.0540(10) Uani 1 1 d . . .
H15A H -0.0169 0.8716 -0.0187 0.081 Uiso 1 1 calc R . .
H15B H -0.0291 0.9279 -0.0958 0.081 Uiso 1 1 calc R . .
H15C H 0.0185 0.9262 -0.0478 0.081 Uiso 1 1 calc R . .
C16 C 0.00940(13) 0.7863(5) -0.1590(2) 0.0707(13) Uani 1 1 d . . .
H16A H 0.0371 0.8215 -0.1478 0.106 Uiso 1 1 calc R . .
H16B H -0.0111 0.8382 -0.1902 0.106 Uiso 1 1 calc R . .
H16C H 0.0095 0.7116 -0.1827 0.106 Uiso 1 1 calc R . .
C17 C 0.12910(9) 0.9630(3) -0.14888(16) 0.0435(8) Uani 1 1 d . . .
C18 C 0.09628(11) 1.0408(4) -0.1331(2) 0.0607(11) Uani 1 1 d . . .
H18A H 0.0720 0.9939 -0.1328 0.091 Uiso 1 1 calc R . .
H18B H 0.0878 1.1011 -0.1693 0.091 Uiso 1 1 calc R . .
H18C H 0.1080 1.0774 -0.0869 0.091 Uiso 1 1 calc R . .
C19 C 0.16640(11) 1.0356(3) -0.15026(19) 0.0503(9) Uani 1 1 d . . .
H19A H 0.1786 1.0719 -0.1041 0.076 Uiso 1 1 calc R . .
H19B H 0.1575 1.0961 -0.1863 0.076 Uiso 1 1 calc R . .
H19C H 0.1872 0.9858 -0.1613 0.076 Uiso 1 1 calc R . .
C20 C 0.11100(13) 0.9046(4) -0.22005(19) 0.0691(13) Uani 1 1 d . . .
H20A H 0.1323 0.8558 -0.2303 0.104 Uiso 1 1 calc R . .
H20B H 0.1018 0.9641 -0.2567 0.104 Uiso 1 1 calc R . .
H20C H 0.0872 0.8562 -0.2190 0.104 Uiso 1 1 calc R . .
C21 C 0.16715(9) 1.0300(3) 0.09200(15) 0.0377(7) Uani 1 1 d . . .
C22 C 0.20280(11) 1.1165(4) 0.1086(2) 0.0556(10) Uani 1 1 d . . .
H22A H 0.2290 1.0754 0.1131 0.083 Uiso 1 1 calc R . .
H22B H 0.2045 1.1565 0.1529 0.083 Uiso 1 1 calc R . .
H22C H 0.1979 1.1736 0.0704 0.083 Uiso 1 1 calc R . .
C23 C 0.12659(10) 1.0947(3) 0.08539(18) 0.0474(8) Uani 1 1 d . . .
H23A H 0.1225 1.1549 0.0491 0.071 Uiso 1 1 calc R . .
H23B H 0.1280 1.1310 0.1306 0.071 Uiso 1 1 calc R . .
H23C H 0.1033 1.0398 0.0722 0.071 Uiso 1 1 calc R . .
C24 C 0.17464(11) 0.9372(3) 0.14960(17) 0.0492(9) Uani 1 1 d . . .
H24A H 0.1520 0.8801 0.1369 0.074 Uiso 1 1 calc R . .
H24B H 0.1755 0.9740 0.1944 0.074 Uiso 1 1 calc R . .
H24C H 0.2012 0.8981 0.1544 0.074 Uiso 1 1 calc R . .
N1 N 0.16699(7) 0.7415(2) 0.01570(14) 0.0364(6) Uani 1 1 d . . .
H1 H 0.1936 0.7424 0.0186 0.044 Uiso 1 1 calc R . .
N2 N 0.09594(7) 0.8566(2) -0.00496(12) 0.0335(6) Uani 1 1 d . . .
N3 N 0.10204(7) 0.6298(2) 0.03459(13) 0.0344(6) Uani 1 1 d . . .
N4 N 0.18146(8) 0.6057(3) 0.12215(14) 0.0425(7) Uani 1 1 d . . .
H4 H 0.1976 0.6663 0.1372 0.051 Uiso 1 1 calc R . .
N5 N 0.15830(8) 0.5040(2) 0.00085(13) 0.0375(6) Uani 1 1 d . . .
H5 H 0.1809 0.4645 0.0224 0.045 Uiso 1 1 calc R . .
N6 N 0.05900(7) 0.7968(2) 0.08269(13) 0.0343(6) Uani 1 1 d . . .
H6 H 0.0609 0.8728 0.0875 0.041 Uiso 1 1 calc R . .
N7 N 0.03193(7) 0.6994(2) -0.04228(13) 0.0361(6) Uani 1 1 d . . .
H7 H 0.0290 0.6234 -0.0454 0.043 Uiso 1 1 calc R . .
N8 N 0.14234(8) 0.8678(2) -0.09624(13) 0.0376(6) Uani 1 1 d . . .
H8 H 0.1527 0.8058 -0.1108 0.045 Uiso 1 1 calc R . .
N9 N 0.16526(7) 0.9775(2) 0.02259(12) 0.0328(6) Uani 1 1 d . . .
H9 H 0.1797 1.0141 -0.0013 0.039 Uiso 1 1 calc R . .
P1 P 0.14035(2) 0.86229(7) -0.01540(4) 0.0310(2) Uani 1 1 d . . .
P2 P 0.14950(2) 0.61893(7) 0.04200(4) 0.0312(2) Uani 1 1 d . . .
P3 P 0.07426(2) 0.74531(7) 0.01731(4) 0.0313(2) Uani 1 1 d . . .
Cl1 Cl 0.22953(4) 0.73736(10) 0.88161(7) 0.0478(3) Uani 0.70 1 d P . .
Cl1A Cl 0.2397(4) 0.7677(9) 0.8111(5) 0.107(3) Uani 0.15 1 d PU . .
Cl1B Cl 0.1864(4) 0.7105(13) 0.8299(6) 0.130(4) Uani 0.15 1 d PU . .
O1 O 0.25023(6) 0.9508(2) 0.99444(12) 0.0460(6) 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 N4 1.471(4) . ?
C1 C3 1.511(5) . ?
C1 C4 1.519(5) . ?
C1 C2 1.537(5) . ?
C5 N5 1.503(4) . ?
C5 C7 1.514(5) . ?
C5 C6 1.522(5) . ?
C5 C8 1.527(5) . ?
C9 N6 1.479(4) . ?
C9 C11 1.514(5) . ?
C9 C10 1.523(5) . ?
C9 C12 1.530(5) . ?
C13 N7 1.480(4) . ?
C13 C15 1.511(5) . ?
C13 C14 1.524(5) . ?
C13 C16 1.521(5) . ?
C17 N8 1.488(4) . ?
C17 C19 1.515(5) . ?
C17 C20 1.520(5) . ?
C17 C18 1.526(5) . ?
C21 N9 1.491(4) . ?
C21 C22 1.517(5) . ?
C21 C23 1.526(4) . ?
C21 C24 1.531(5) . ?
N1 P1 1.669(3) . ?
N1 P2 1.671(3) . ?
N2 P1 1.571(2) . ?
N2 P3 1.600(3) . ?
N3 P2 1.564(2) . ?
N3 P3 1.602(3) . ?
N4 P2 1.642(3) . ?
N5 P2 1.628(3) . ?
N6 P3 1.645(2) . ?
N7 P3 1.644(3) . ?
N8 P1 1.631(3) . ?
N9 P1 1.629(3) . ?
Cl1 Cl1B 1.537(11) . ?
Cl1 Cl1A 1.580(12) . ?
Cl1A Cl1B 2.048(17) . ?
 
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
N4 C1 C3 110.2(3) . . ?
N4 C1 C4 112.1(3) . . ?
C3 C1 C4 110.7(3) . . ?
N4 C1 C2 107.2(3) . . ?
C3 C1 C2 108.8(3) . . ?
C4 C1 C2 107.8(3) . . ?
N5 C5 C7 109.1(3) . . ?
N5 C5 C6 105.1(3) . . ?
C7 C5 C6 109.4(3) . . ?
N5 C5 C8 111.5(3) . . ?
C7 C5 C8 111.8(3) . . ?
C6 C5 C8 109.7(3) . . ?
N6 C9 C11 110.7(3) . . ?
N6 C9 C10 108.8(3) . . ?
C11 C9 C10 109.8(3) . . ?
N6 C9 C12 108.1(3) . . ?
C11 C9 C12 110.0(3) . . ?
C10 C9 C12 109.4(3) . . ?
N7 C13 C15 111.5(3) . . ?
N7 C13 C14 108.5(3) . . ?
C15 C13 C14 109.6(3) . . ?
N7 C13 C16 108.2(3) . . ?
C15 C13 C16 109.0(3) . . ?
C14 C13 C16 110.0(3) . . ?
N8 C17 C19 110.1(3) . . ?
N8 C17 C20 106.4(3) . . ?
C19 C17 C20 109.3(3) . . ?
N8 C17 C18 111.7(3) . . ?
C19 C17 C18 109.6(3) . . ?
C20 C17 C18 109.8(3) . . ?
N9 C21 C22 106.2(3) . . ?
N9 C21 C23 109.2(2) . . ?
C22 C21 C23 109.1(3) . . ?
N9 C21 C24 111.3(3) . . ?
C22 C21 C24 110.7(3) . . ?
C23 C21 C24 110.3(3) . . ?
P1 N1 P2 128.20(14) . . ?
P1 N2 P3 126.95(16) . . ?
P2 N3 P3 126.89(17) . . ?
C1 N4 P2 130.9(2) . . ?
C5 N5 P2 128.4(2) . . ?
C9 N6 P3 131.0(2) . . ?
C13 N7 P3 129.6(2) . . ?
C17 N8 P1 129.1(2) . . ?
C21 N9 P1 129.2(2) . . ?
N2 P1 N9 110.53(13) . . ?
N2 P1 N8 117.00(13) . . ?
N9 P1 N8 104.98(13) . . ?
N2 P1 N1 110.02(13) . . ?
N9 P1 N1 111.19(13) . . ?
N8 P1 N1 102.82(14) . . ?
N3 P2 N5 110.61(14) . . ?
N3 P2 N4 116.89(14) . . ?
N5 P2 N4 104.37(14) . . ?
N3 P2 N1 110.39(13) . . ?
N5 P2 N1 113.17(13) . . ?
N4 P2 N1 101.10(14) . . ?
N2 P3 N3 115.97(13) . . ?
N2 P3 N6 101.95(13) . . ?
N3 P3 N6 115.43(13) . . ?
N2 P3 N7 115.20(13) . . ?
N3 P3 N7 102.25(14) . . ?
N6 P3 N7 106.12(13) . . ?
Cl1B Cl1 Cl1A 82.1(6) . . ?
Cl1 Cl1A Cl1B 48.0(5) . . ?
Cl1 Cl1B Cl1A 49.8(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    1.451
_refine_diff_density_min   -0.540
_refine_diff_density_rms    0.101
