data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H32 Cl2 N3 Na0 O10 P3'
_chemical_formula_weight          590.26
 
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'
 'Na'  'Na'   0.0362   0.0249
 '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                    14.261(3)
_cell_length_b                    11.346(2)
_cell_length_c                    17.586(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.22(3)
_cell_angle_gamma                 90.00
_cell_volume                      2686.8(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     26449
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.25
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.459
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1232
_exptl_absorpt_coefficient_mu     0.472
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.8335
_exptl_absorpt_correction_T_max   0.8910
_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             39224
_diffrn_reflns_av_R_equivalents   0.0676
_diffrn_reflns_av_sigmaI/netI     0.0416
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          27.47
_reflns_number_total              6125
_reflns_number_gt                 4867
_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)+(0.0524P)²+0.5132P] 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        0.0000(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          6125
_refine_ls_number_parameters      308
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0521
_refine_ls_R_factor_gt            0.0362
_refine_ls_wR_factor_ref          0.0964
_refine_ls_wR_factor_gt           0.0895
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_refine_ls_shift/su_max           0.093
_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 0.32836(13) -0.31235(16) 0.26041(11) 0.0278(4) Uani 1 1 d . . .
H1A H 0.3873 -0.2608 0.2812 0.033 Uiso 1 1 calc R . .
H1B H 0.3300 -0.3480 0.2095 0.033 Uiso 1 1 calc R . .
C2 C 0.33436(13) -0.40840(16) 0.32014(12) 0.0298(4) Uani 1 1 d . . .
H2A H 0.3983 -0.4509 0.3324 0.036 Uiso 1 1 calc R . .
H2B H 0.3302 -0.3746 0.3708 0.036 Uiso 1 1 calc R . .
C3 C 0.26306(18) -0.59644(18) 0.32864(14) 0.0436(5) Uani 1 1 d . . .
H3A H 0.3339 -0.6197 0.3483 0.052 Uiso 1 1 calc R . .
H3B H 0.2261 -0.6580 0.2907 0.052 Uiso 1 1 calc R . .
C4 C 0.22555(17) -0.59235(19) 0.39872(14) 0.0426(5) Uani 1 1 d . . .
H4A H 0.1570 -0.5607 0.3811 0.051 Uiso 1 1 calc R . .
H4B H 0.2241 -0.6730 0.4198 0.051 Uiso 1 1 calc R . .
C5 C 0.24748(16) -0.49163(18) 0.52122(13) 0.0369(5) Uani 1 1 d . . .
H5A H 0.2493 -0.5620 0.5550 0.044 Uiso 1 1 calc R . .
H5B H 0.1773 -0.4673 0.4964 0.044 Uiso 1 1 calc R . .
C6 C 0.30608(16) -0.39309(18) 0.57268(12) 0.0373(5) Uani 1 1 d . . .
H6A H 0.2774 -0.3755 0.6156 0.045 Uiso 1 1 calc R . .
H6B H 0.3752 -0.4202 0.5990 0.045 Uiso 1 1 calc R . .
C7 C 0.21779(13) -0.22344(17) 0.50606(11) 0.0304(4) Uani 1 1 d . . .
H7A H 0.2087 -0.1839 0.5534 0.037 Uiso 1 1 calc R . .
H7B H 0.1611 -0.2774 0.4826 0.037 Uiso 1 1 calc R . .
C8 C 0.22256(14) -0.13335(16) 0.44464(11) 0.0279(4) Uani 1 1 d . . .
H8A H 0.1634 -0.0816 0.4303 0.033 Uiso 1 1 calc R . .
H8B H 0.2828 -0.0840 0.4660 0.033 Uiso 1 1 calc R . .
C9 C 0.47941(12) 0.13815(17) 0.42242(11) 0.0273(4) Uani 1 1 d . . .
H9A H 0.5327 0.1736 0.4054 0.033 Uiso 1 1 calc R . .
H9B H 0.4915 0.0523 0.4294 0.033 Uiso 1 1 calc R . .
C10 C 0.47852(13) 0.19220(17) 0.49950(11) 0.0296(4) Uani 1 1 d . . .
H10A H 0.5456 0.1877 0.5403 0.036 Uiso 1 1 calc R . .
H10B H 0.4590 0.2762 0.4909 0.036 Uiso 1 1 calc R . .
C11 C 0.39781(14) 0.18074(19) 0.59641(11) 0.0352(5) Uani 1 1 d . . .
H11A H 0.3880 0.2669 0.5888 0.042 Uiso 1 1 calc R . .
H11B H 0.4583 0.1671 0.6433 0.042 Uiso 1 1 calc R . .
C12 C 0.31005(14) 0.1268(2) 0.61158(11) 0.0365(5) Uani 1 1 d . . .
H12A H 0.3156 0.0398 0.6125 0.044 Uiso 1 1 calc R . .
H12B H 0.3067 0.1533 0.6643 0.044 Uiso 1 1 calc R . .
C13 C 0.13540(14) 0.11898(19) 0.55889(12) 0.0349(5) Uani 1 1 d . . .
H13A H 0.1303 0.1466 0.6108 0.042 Uiso 1 1 calc R . .
H13B H 0.1362 0.0317 0.5593 0.042 Uiso 1 1 calc R . .
C14 C 0.04860(14) 0.1628(2) 0.49055(12) 0.0364(5) Uani 1 1 d . . .
H14A H -0.0138 0.1463 0.5018 0.044 Uiso 1 1 calc R . .
H14B H 0.0541 0.2491 0.4850 0.044 Uiso 1 1 calc R . .
C15 C -0.02757(14) 0.15728(19) 0.35044(11) 0.0335(4) Uani 1 1 d . . .
H15A H -0.0172 0.2435 0.3498 0.040 Uiso 1 1 calc R . .
H15B H -0.0943 0.1430 0.3544 0.040 Uiso 1 1 calc R . .
C16 C -0.02101(13) 0.10371(18) 0.27481(12) 0.0312(4) Uani 1 1 d . . .
H16A H -0.0208 0.0167 0.2788 0.037 Uiso 1 1 calc R . .
H16B H -0.0789 0.1278 0.2284 0.037 Uiso 1 1 calc R . .
N1 N 0.33284(10) -0.05797(12) 0.32362(9) 0.0224(3) Uani 1 1 d . . .
N2 N 0.23420(10) 0.12845(12) 0.23631(9) 0.0233(3) Uani 1 1 d . . .
N3 N 0.13355(10) -0.06763(12) 0.25368(9) 0.0247(3) Uani 1 1 d . . .
O1 O 0.24012(8) -0.24161(10) 0.24398(7) 0.0227(3) Uani 1 1 d . . .
O2 O 0.25382(10) -0.48724(11) 0.28603(8) 0.0343(3) Uani 1 1 d . . .
O3 O 0.28862(10) -0.51928(12) 0.46044(8) 0.0367(3) Uani 1 1 d . . .
O4 O 0.30791(9) -0.28722(12) 0.52950(8) 0.0315(3) Uani 1 1 d . . .
O5 O 0.22553(9) -0.19928(10) 0.37512(7) 0.0249(3) Uani 1 1 d . . .
O6 O 0.38232(8) 0.16050(10) 0.36173(7) 0.0243(3) Uani 1 1 d . . .
O7 O 0.40953(9) 0.12949(11) 0.52649(7) 0.0292(3) Uani 1 1 d . . .
O8 O 0.22343(9) 0.16268(13) 0.54879(8) 0.0364(3) Uani 1 1 d . . .
O9 O 0.04620(9) 0.10627(12) 0.41789(8) 0.0326(3) Uani 1 1 d . . .
O10 O 0.07108(9) 0.14463(11) 0.26361(8) 0.0287(3) Uani 1 1 d . . .
P1 P 0.23370(3) -0.13463(4) 0.29886(3) 0.01980(12) Uani 1 1 d . . .
P2 P 0.33434(3) 0.07179(4) 0.29258(3) 0.01910(11) Uani 1 1 d . . .
P3 P 0.13231(3) 0.06407(4) 0.22583(3) 0.02013(12) Uani 1 1 d . . .
Cl1 Cl 0.43420(3) 0.07510(4) 0.23253(3) 0.03341(13) Uani 1 1 d . . .
Cl2 Cl 0.05116(3) 0.06820(5) 0.10708(3) 0.03579(14) 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 1.440(2) . ?
C1 C2 1.496(3) . ?
C2 O2 1.423(2) . ?
C3 O2 1.431(2) . ?
C3 C4 1.497(3) . ?
C4 O3 1.425(3) . ?
C5 O3 1.413(2) . ?
C5 C6 1.506(3) . ?
C6 O4 1.426(2) . ?
C7 O4 1.413(2) . ?
C7 C8 1.505(3) . ?
C8 O5 1.446(2) . ?
C9 O6 1.465(2) . ?
C9 C10 1.492(3) . ?
C10 O7 1.417(2) . ?
C11 O7 1.419(2) . ?
C11 C12 1.494(3) . ?
C12 O8 1.419(2) . ?
C13 O8 1.414(2) . ?
C13 C14 1.498(3) . ?
C14 O9 1.420(2) . ?
C15 O9 1.424(2) . ?
C15 C16 1.493(3) . ?
C16 O10 1.466(2) . ?
N1 P2 1.5727(14) . ?
N1 P1 1.5937(14) . ?
N2 P2 1.5816(15) . ?
N2 P3 1.5821(14) . ?
N3 P3 1.5707(15) . ?
N3 P1 1.5817(15) . ?
O1 P1 1.5720(12) . ?
O5 P1 1.5662(13) . ?
O6 P2 1.5532(12) . ?
O10 P3 1.5559(13) . ?
P2 Cl1 2.0333(8) . ?
P3 Cl2 2.0277(9) . ?
 
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 113.02(14) . . ?
O2 C2 C1 108.06(15) . . ?
O2 C3 C4 114.07(17) . . ?
O3 C4 C3 109.76(18) . . ?
O3 C5 C6 109.44(16) . . ?
O4 C6 C5 114.14(16) . . ?
O4 C7 C8 107.79(14) . . ?
O5 C8 C7 106.05(14) . . ?
O6 C9 C10 107.58(14) . . ?
O7 C10 C9 108.22(14) . . ?
O7 C11 C12 109.35(16) . . ?
O8 C12 C11 108.02(17) . . ?
O8 C13 C14 108.43(17) . . ?
O9 C14 C13 109.92(15) . . ?
O9 C15 C16 109.33(15) . . ?
O10 C16 C15 108.20(16) . . ?
P2 N1 P1 121.88(9) . . ?
P2 N2 P3 119.39(9) . . ?
P3 N3 P1 121.97(9) . . ?
C1 O1 P1 122.08(11) . . ?
C2 O2 C3 113.63(16) . . ?
C5 O3 C4 112.95(16) . . ?
C7 O4 C6 114.36(14) . . ?
C8 O5 P1 120.86(11) . . ?
C9 O6 P2 121.68(11) . . ?
C10 O7 C11 112.18(14) . . ?
C13 O8 C12 112.52(15) . . ?
C14 O9 C15 111.00(14) . . ?
C16 O10 P3 121.65(12) . . ?
O5 P1 O1 101.53(7) . . ?
O5 P1 N3 110.23(8) . . ?
O1 P1 N3 106.75(8) . . ?
O5 P1 N1 109.33(8) . . ?
O1 P1 N1 111.31(7) . . ?
N3 P1 N1 116.63(8) . . ?
O6 P2 N1 112.81(7) . . ?
O6 P2 N2 107.51(8) . . ?
N1 P2 N2 119.02(7) . . ?
O6 P2 Cl1 101.03(5) . . ?
N1 P2 Cl1 106.82(6) . . ?
N2 P2 Cl1 108.06(6) . . ?
O10 P3 N3 112.09(8) . . ?
O10 P3 N2 107.58(8) . . ?
N3 P3 N2 119.16(8) . . ?
O10 P3 Cl2 102.47(6) . . ?
N3 P3 Cl2 106.69(6) . . ?
N2 P3 Cl2 107.47(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.616
_refine_diff_density_min   -0.402
_refine_diff_density_rms    0.062
