 
data_04src0238 
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H24 Cl3 N4 O5 P3'
_chemical_formula_weight          491.60
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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)/n
_symmetry_spacE_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    12.342(3)
_cell_length_b                    14.132(3)
_cell_length_c                    12.611(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.835(18)
_cell_angle_gamma                 90.00
_cell_volume                      2199.3(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     46150
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.35
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.485
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1016
_exptl_absorpt_coefficient_mu     0.663
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.7327
_exptl_absorpt_correction_T_max   0.8011
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             29053
_diffrn_reflns_av_R_equivalents   0.0720
_diffrn_reflns_av_sigmaI/netI     0.0389
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.23
_diffrn_reflns_theta_max          27.50
_reflns_number_total              5047
_reflns_number_gt                 3746
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_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)+(0.0689P)²+1.6755P] 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        0.0035(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5047
_refine_ls_number_parameters      240
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0822
_refine_ls_R_factor_gt            0.0591
_refine_ls_wR_factor_ref          0.1592
_refine_ls_wR_factor_gt           0.1452
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.046
_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 0.8986(3) 0.0233(2) 1.1462(3) 0.0653(9) Uani 1 1 d . . .
H1A H 0.9006 0.0074 1.0698 0.078 Uiso 1 1 calc R . .
H1B H 0.8553 -0.0255 1.1827 0.078 Uiso 1 1 calc R . .
C2 C 1.0102(3) 0.0253(3) 1.1912(3) 0.0730(10) Uani 1 1 d . . .
H2A H 1.0099 0.0550 1.2623 0.088 Uiso 1 1 calc R . .
H2B H 1.0380 -0.0401 1.1990 0.088 Uiso 1 1 calc R . .
C3 C 1.1858(4) 0.0787(3) 1.1627(4) 0.0836(12) Uani 1 1 d . . .
H3A H 1.2118 0.0132 1.1742 0.100 Uiso 1 1 calc R . .
H3B H 1.1889 0.1123 1.2316 0.100 Uiso 1 1 calc R . .
C4 C 1.2565(4) 0.1274(4) 1.0859(4) 0.0967(15) Uani 1 1 d . . .
H4A H 1.3334 0.1191 1.1074 0.116 Uiso 1 1 calc R . .
H4B H 1.2462 0.0991 1.0146 0.116 Uiso 1 1 calc R . .
C5 C 1.2900(4) 0.2831(5) 1.0101(4) 0.1038(17) Uani 1 1 d . . .
H5A H 1.3653 0.2593 1.0066 0.125 Uiso 1 1 calc R . .
H5B H 1.2931 0.3482 1.0388 0.125 Uiso 1 1 calc R . .
C6 C 1.2453(4) 0.2866(5) 0.9044(4) 0.1039(17) Uani 1 1 d . . .
H6A H 1.2921 0.3259 0.8589 0.125 Uiso 1 1 calc R . .
H6B H 1.2423 0.2220 0.8741 0.125 Uiso 1 1 calc R . .
C7 C 1.0632(4) 0.2647(5) 0.8650(5) 0.120(2) Uani 1 1 d . . .
H7A H 1.0738 0.2595 0.7876 0.144 Uiso 1 1 calc R . .
H7B H 1.0751 0.2012 0.8962 0.144 Uiso 1 1 calc R . .
C8 C 0.9632(4) 0.2903(4) 0.8820(6) 0.138(3) Uani 1 1 d . . .
H8A H 0.9544 0.3571 0.8601 0.166 Uiso 1 1 calc R . .
H8B H 0.9498 0.2868 0.9591 0.166 Uiso 1 1 calc R . .
C9 C 0.5982(3) 0.1264(2) 0.7847(3) 0.0570(8) Uani 1 1 d . . .
H9 H 0.5973 0.0866 0.8503 0.068 Uiso 1 1 calc R . .
C10 C 0.5063(3) 0.1967(4) 0.7903(5) 0.1022(16) Uani 1 1 d . . .
H10A H 0.5165 0.2372 0.8527 0.153 Uiso 1 1 calc R . .
H10B H 0.4374 0.1626 0.7956 0.153 Uiso 1 1 calc R . .
H10C H 0.5053 0.2358 0.7261 0.153 Uiso 1 1 calc R . .
C11 C 0.5852(3) 0.0622(3) 0.6902(3) 0.0783(11) Uani 1 1 d . . .
H11A H 0.6445 0.0160 0.6899 0.117 Uiso 1 1 calc R . .
H11B H 0.5870 0.0999 0.6250 0.117 Uiso 1 1 calc R . .
H11C H 0.5158 0.0289 0.6941 0.117 Uiso 1 1 calc R . .
N1 N 0.7255(3) 0.2534(2) 1.1278(2) 0.0676(8) Uani 1 1 d . . .
N2 N 0.7788(2) 0.13485(18) 0.96777(19) 0.0569(7) Uani 1 1 d . . .
N3 N 0.7262(2) 0.31408(19) 0.9245(2) 0.0617(7) Uani 1 1 d . . .
N4 N 0.7034(2) 0.1737(2) 0.7796(2) 0.0517(6) Uani 1 1 d . . .
O1 O 0.8494(2) 0.11575(16) 1.16038(16) 0.0631(6) Uani 1 1 d . . .
O2 O 1.0775(2) 0.07697(18) 1.12378(19) 0.0693(6) Uani 1 1 d . . .
O3 O 1.2310(2) 0.2247(2) 1.0822(2) 0.0787(7) Uani 1 1 d . . .
O4 O 1.1396(2) 0.3257(2) 0.9063(3) 0.0969(10) Uani 1 1 d . . .
O5 O 0.88196(19) 0.2340(2) 0.82706(19) 0.0705(7) Uani 1 1 d . . .
P1 P 0.70593(7) 0.33362(6) 1.04385(7) 0.0568(2) Uani 1 1 d . . .
P2 P 0.75542(7) 0.15089(6) 1.08777(6) 0.0548(2) Uani 1 1 d . . .
P3 P 0.76963(6) 0.21457(6) 0.87996(6) 0.0491(2) Uani 1 1 d . . .
Cl1 Cl 0.55524(9) 0.38326(10) 1.06060(11) 0.1028(4) Uani 1 1 d . . .
Cl2 Cl 0.78870(10) 0.44771(8) 1.09158(9) 0.0889(4) Uani 1 1 d . . .
Cl3 Cl 0.63363(10) 0.06188(9) 1.12548(11) 0.0961(4) Uani 1 1 d . . .
H4N H 0.714(2) 0.197(2) 0.734(2) 0.035(9) Uiso 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 1.453(4) . ?
C1 C2 1.483(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.403(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.418(5) . ?
C3 C4 1.482(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.412(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O3 1.434(5) . ?
C5 C6 1.436(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.416(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.306(7) . ?
C7 O4 1.375(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O5 1.448(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N4 1.462(4) . ?
C9 C11 1.505(5) . ?
C9 C10 1.511(5) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 P1 1.568(3) . ?
N1 P2 1.579(3) . ?
N2 P2 1.561(3) . ?
N2 P3 1.583(3) . ?
N3 P1 1.553(3) . ?
N3 P3 1.609(3) . ?
N4 P3 1.604(3) . ?
N4 H4N 0.67(3) . ?
O1 P2 1.549(2) . ?
O5 P3 1.571(2) . ?
P1 Cl2 1.9968(14) . ?
P1 Cl1 2.0019(14) . ?
P2 Cl3 2.0220(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 108.9(3) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
O2 C2 C1 109.4(3) . . ?
O2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 C4 110.1(4) . . ?
O2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
O2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 C3 109.9(3) . . ?
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 114.6(4) . . ?
O3 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
O3 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
O4 C6 C5 109.8(4) . . ?
O4 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
O4 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 O4 114.2(5) . . ?
C8 C7 H7A 108.7 . . ?
O4 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
O4 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 O5 114.8(5) . . ?
C7 C8 H8A 108.6 . . ?
O5 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
O5 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
N4 C9 C11 109.0(3) . . ?
N4 C9 C10 111.7(3) . . ?
C11 C9 C10 111.2(3) . . ?
N4 C9 H9 108.3 . . ?
C11 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
P1 N1 P2 118.82(17) . . ?
P2 N2 P3 124.23(17) . . ?
P1 N3 P3 123.56(17) . . ?
C9 N4 P3 124.9(2) . . ?
C9 N4 H4N 116(3) . . ?
P3 N4 H4N 113(3) . . ?
C1 O1 P2 121.8(2) . . ?
C2 O2 C3 111.3(3) . . ?
C4 O3 C5 117.8(4) . . ?
C7 O4 C6 112.1(4) . . ?
C8 O5 P3 120.1(3) . . ?
N3 P1 N1 120.00(15) . . ?
N3 P1 Cl2 110.29(13) . . ?
N1 P1 Cl2 107.91(13) . . ?
N3 P1 Cl1 109.11(12) . . ?
N1 P1 Cl1 108.44(13) . . ?
Cl2 P1 Cl1 99.05(7) . . ?
O1 P2 N2 112.27(14) . . ?
O1 P2 N1 106.36(15) . . ?
N2 P2 N1 119.36(15) . . ?
O1 P2 Cl3 102.39(11) . . ?
N2 P2 Cl3 106.63(12) . . ?
N1 P2 Cl3 108.48(13) . . ?
O5 P3 N2 111.52(15) . . ?
O5 P3 N4 99.84(14) . . ?
N2 P3 N4 109.02(15) . . ?
O5 P3 N3 107.24(16) . . ?
N2 P3 N3 113.47(14) . . ?
N4 P3 N3 114.93(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.612
_refine_diff_density_min   -0.298
_refine_diff_density_rms    0.074
