data_01src1036
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H23 Cl2 N4 O6 P3'
_chemical_formula_weight          471.14
 
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    P2(1)/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.6830(7)
_cell_length_b                    12.7753(11)
_cell_length_c                    17.2103(17)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.513(4)
_cell_angle_gamma                 90.00
_cell_volume                      1909.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     18664
_cell_measurement_theta_min       1.0
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.639
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              976
_exptl_absorpt_coefficient_mu     0.629
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8638
_exptl_absorpt_correction_T_max   0.9937
_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          ?
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12301
_diffrn_reflns_av_R_equivalents   0.1124
_diffrn_reflns_av_sigmaI/netI     0.1826
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.37
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4275
_reflns_number_gt                 2114
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0502P)²+0.0000P] 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        0.0010(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4275
_refine_ls_number_parameters      240
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1698
_refine_ls_R_factor_gt            0.0608
_refine_ls_wR_factor_ref          0.1357
_refine_ls_wR_factor_gt           0.1054
_refine_ls_goodness_of_fit_ref    0.959
_refine_ls_restrained_S_all       0.959
_refine_ls_shift/su_max           0.101
_refine_ls_shift/su_mean          0.005
 
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 -0.0821(6) 0.5818(3) 0.0807(3) 0.0302(12) Uani 1 1 d . . .
H1A H 0.0249 0.5619 0.0943 0.036 Uiso 1 1 calc R . .
H1B H -0.0976 0.5711 0.0241 0.036 Uiso 1 1 calc R . .
C2 C -0.1929(6) 0.5166(4) 0.1250(3) 0.0319(12) Uani 1 1 d . . .
H2A H -0.3000 0.5362 0.1113 0.038 Uiso 1 1 calc R . .
H2B H -0.1782 0.4416 0.1126 0.038 Uiso 1 1 calc R . .
C3 C -0.2787(6) 0.4912(3) 0.2536(3) 0.0318(12) Uani 1 1 d . . .
H3A H -0.2698 0.4139 0.2541 0.038 Uiso 1 1 calc R . .
H3B H -0.3824 0.5098 0.2336 0.038 Uiso 1 1 calc R . .
C4 C -0.2575(6) 0.5331(3) 0.3340(3) 0.0317(12) Uani 1 1 d . . .
H4A H -0.3204 0.4920 0.3708 0.038 Uiso 1 1 calc R . .
H4B H -0.1481 0.5266 0.3500 0.038 Uiso 1 1 calc R . .
C5 C -0.2839(6) 0.6844(3) 0.4124(3) 0.0293(11) Uani 1 1 d . . .
H5A H -0.1804 0.6667 0.4332 0.035 Uiso 1 1 calc R . .
H5B H -0.3617 0.6545 0.4478 0.035 Uiso 1 1 calc R . .
C6 C -0.3020(6) 0.8011(4) 0.4090(3) 0.0343(13) Uani 1 1 d . . .
H6A H -0.3910 0.8179 0.3748 0.041 Uiso 1 1 calc R . .
H6B H -0.3259 0.8271 0.4617 0.041 Uiso 1 1 calc R . .
C7 C -0.1687(6) 0.8802(3) 0.3011(2) 0.0323(12) Uani 1 1 d . . .
H7A H -0.1185 0.9491 0.2940 0.039 Uiso 1 1 calc R . .
H7B H -0.2758 0.8857 0.2813 0.039 Uiso 1 1 calc R . .
C8 C -0.0847(6) 0.7996(4) 0.2552(3) 0.0370(13) Uani 1 1 d . . .
H8A H 0.0133 0.7810 0.2816 0.044 Uiso 1 1 calc R . .
H8B H -0.1479 0.7355 0.2500 0.044 Uiso 1 1 calc R . .
C9 C 0.3272(6) 0.9934(4) -0.0950(3) 0.0345(13) Uani 1 1 d . . .
H9A H 0.4337 0.9765 -0.0781 0.041 Uiso 1 1 calc R . .
H9B H 0.3237 1.0685 -0.1089 0.041 Uiso 1 1 calc R . .
C10 C 0.2859(6) 0.9286(4) -0.1655(3) 0.0374(13) Uani 1 1 d . . .
H10A H 0.1846 0.9518 -0.1861 0.045 Uiso 1 1 calc R . .
H10B H 0.3633 0.9407 -0.2064 0.045 Uiso 1 1 calc R . .
C11 C 0.2787(6) 0.8137(4) -0.1478(3) 0.0346(12) Uani 1 1 d . . .
H11A H 0.2501 0.7748 -0.1955 0.042 Uiso 1 1 calc R . .
H11B H 0.3816 0.7891 -0.1305 0.042 Uiso 1 1 calc R . .
N1 N 0.0369(4) 0.8461(3) 0.04063(19) 0.0259(9) Uani 1 1 d . . .
N2 N 0.3431(4) 0.8071(3) 0.0334(2) 0.0259(9) Uani 1 1 d . . .
N3 N 0.1724(4) 0.7178(3) 0.1463(2) 0.0254(9) Uani 1 1 d . . .
N4 N 0.1671(4) 0.7922(2) -0.08763(17) 0.0135(8) Uani 1 1 d D . .
P1 P 0.01873(14) 0.77401(9) 0.11449(7) 0.0247(3) Uani 1 1 d . . .
P2 P 0.18929(14) 0.85307(9) -0.00787(7) 0.0244(3) Uani 1 1 d . . .
P3 P 0.32609(14) 0.72531(9) 0.10006(7) 0.0240(3) Uani 1 1 d . . .
Cl1 Cl 0.50045(13) 0.74350(9) 0.17586(7) 0.0317(3) Uani 1 1 d . . .
Cl2 Cl 0.37677(14) 0.57971(8) 0.06032(7) 0.0351(3) Uani 1 1 d . . .
O1 O -0.1091(3) 0.6898(2) 0.10051(18) 0.0291(8) Uani 1 1 d . . .
O2 O -0.1647(4) 0.5345(2) 0.20519(17) 0.0297(8) Uani 1 1 d . . .
O3 O -0.3030(3) 0.6406(2) 0.33631(16) 0.0282(8) Uani 1 1 d . . .
O4 O -0.1708(4) 0.8552(3) 0.38126(17) 0.0385(9) Uani 1 1 d . . .
O5 O -0.0542(3) 0.8441(2) 0.17883(16) 0.0248(8) Uani 1 1 d . . .
O6 O 0.2208(4) 0.9735(3) -0.0302(2) 0.0473(10) Uani 1 1 d . . .
H4N H 0.086(6) 0.739(4) -0.099(5) 0.15(3) Uiso 1 1 d 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 1.441(5) . ?
C1 C2 1.489(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.418(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.412(5) . ?
C3 C4 1.494(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.430(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O3 1.433(5) . ?
C5 C6 1.500(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.419(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O4 1.417(5) . ?
C7 C8 1.492(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O5 1.459(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O6 1.476(5) . ?
C9 C10 1.510(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.501(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.450(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 P2 1.573(4) . ?
N1 P1 1.579(3) . ?
N2 P3 1.560(3) . ?
N2 P2 1.617(4) . ?
N3 P3 1.563(4) . ?
N3 P1 1.607(4) . ?
N4 P2 1.588(3) . ?
N4 H4N 0.9999(13) . ?
P1 O5 1.562(3) . ?
P1 O1 1.563(3) . ?
P2 O6 1.610(4) . ?
P3 Cl1 2.0032(16) . ?
P3 Cl2 2.0314(15) . ?
 
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 107.9(3) . . ?
O1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
O2 C2 C1 107.6(4) . . ?
O2 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O2 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 C4 108.9(4) . . ?
O2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
O2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
O3 C4 C3 109.8(4) . . ?
O3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
O3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O3 C5 C6 109.9(4) . . ?
O3 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
O3 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O4 C6 C5 114.4(4) . . ?
O4 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
O4 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O4 C7 C8 111.8(4) . . ?
O4 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
O4 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O5 C8 C7 107.6(3) . . ?
O5 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
O5 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O6 C9 C10 111.5(4) . . ?
O6 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
O6 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 112.5(4) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N4 C11 C10 111.0(4) . . ?
N4 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N4 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
P2 N1 P1 123.4(2) . . ?
P3 N2 P2 118.9(2) . . ?
P3 N3 P1 120.6(2) . . ?
C11 N4 P2 116.6(3) . . ?
C11 N4 H4N 118(5) . . ?
P2 N4 H4N 126(5) . . ?
O5 P1 O1 102.22(16) . . ?
O5 P1 N1 106.29(17) . . ?
O1 P1 N1 110.71(19) . . ?
O5 P1 N3 110.78(18) . . ?
O1 P1 N3 109.38(18) . . ?
N1 P1 N3 116.49(19) . . ?
N1 P2 N4 109.58(19) . . ?
N1 P2 O6 109.05(19) . . ?
N4 P2 O6 106.31(18) . . ?
N1 P2 N2 116.22(19) . . ?
N4 P2 N2 107.15(18) . . ?
O6 P2 N2 108.07(19) . . ?
N2 P3 N3 120.2(2) . . ?
N2 P3 Cl1 108.98(15) . . ?
N3 P3 Cl1 108.61(15) . . ?
N2 P3 Cl2 110.09(14) . . ?
N3 P3 Cl2 107.70(14) . . ?
Cl1 P3 Cl2 99.25(7) . . ?
C1 O1 P1 125.3(3) . . ?
C3 O2 C2 113.2(3) . . ?
C4 O3 C5 111.8(3) . . ?
C6 O4 C7 117.0(4) . . ?
C8 O5 P1 119.6(3) . . ?
C9 O6 P2 117.0(3) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 C1 C2 O2 -60.2(5) . . . . ?
O2 C3 C4 O3 72.0(5) . . . . ?
O3 C5 C6 O4 -78.5(5) . . . . ?
O4 C7 C8 O5 -165.7(4) . . . . ?
O6 C9 C10 C11 -55.3(5) . . . . ?
C9 C10 C11 N4 58.4(5) . . . . ?
C10 C11 N4 P2 -55.8(5) . . . . ?
P2 N1 P1 O5 132.1(3) . . . . ?
P2 N1 P1 O1 -117.6(3) . . . . ?
P2 N1 P1 N3 8.2(4) . . . . ?
P3 N3 P1 O5 -128.3(2) . . . . ?
P3 N3 P1 O1 119.8(2) . . . . ?
P3 N3 P1 N1 -6.7(3) . . . . ?
P1 N1 P2 N4 105.8(3) . . . . ?
P1 N1 P2 O6 -138.3(3) . . . . ?
P1 N1 P2 N2 -15.9(4) . . . . ?
C11 N4 P2 N1 164.0(3) . . . . ?
C11 N4 P2 O6 46.3(3) . . . . ?
C11 N4 P2 N2 -69.1(3) . . . . ?
P3 N2 P2 N1 22.3(3) . . . . ?
P3 N2 P2 N4 -100.6(2) . . . . ?
P3 N2 P2 O6 145.2(2) . . . . ?
P2 N2 P3 N3 -21.9(3) . . . . ?
P2 N2 P3 Cl1 -148.11(19) . . . . ?
P2 N2 P3 Cl2 104.0(2) . . . . ?
P1 N3 P3 N2 14.0(3) . . . . ?
P1 N3 P3 Cl1 140.4(2) . . . . ?
P1 N3 P3 Cl2 -113.1(2) . . . . ?
C2 C1 O1 P1 139.5(3) . . . . ?
O5 P1 O1 C1 -146.1(3) . . . . ?
N1 P1 O1 C1 101.0(3) . . . . ?
N3 P1 O1 C1 -28.7(4) . . . . ?
C4 C3 O2 C2 -168.1(4) . . . . ?
C1 C2 O2 C3 169.9(3) . . . . ?
C3 C4 O3 C5 -179.7(4) . . . . ?
C6 C5 O3 C4 168.6(4) . . . . ?
C5 C6 O4 C7 95.1(5) . . . . ?
C8 C7 O4 C6 -94.9(5) . . . . ?
C7 C8 O5 P1 -174.0(3) . . . . ?
O1 P1 O5 C8 64.3(4) . . . . ?
N1 P1 O5 C8 -179.6(3) . . . . ?
N3 P1 O5 C8 -52.1(4) . . . . ?
C10 C9 O6 P2 49.6(5) . . . . ?
N1 P2 O6 C9 -161.2(3) . . . . ?
N4 P2 O6 C9 -43.1(4) . . . . ?
N2 P2 O6 C9 71.6(4) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.979
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.979
_refine_diff_density_max    0.500
_refine_diff_density_min   -0.463
_refine_diff_density_rms    0.102
