data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H20.50 Cl2.50 N5 O3 P3'
_chemical_formula_weight          440.35
 
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            Orthorhombic
_symmetry_space_group_name_H-M    Pna2(1)
 
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'
 
_cell_length_a                    15.229(3)
_cell_length_b                    26.120(5)
_cell_length_c                    9.2683(19)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3686.7(13)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     19318
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       7.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.587
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1816
_exptl_absorpt_coefficient_mu     0.705
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.7421
_exptl_absorpt_correction_T_max   0.9202
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(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             24873
_diffrn_reflns_av_R_equivalents   0.0723
_diffrn_reflns_av_sigmaI/netI     0.0619
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -33
_diffrn_reflns_limit_k_max        33
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          27.48
_reflns_number_total              7818
_reflns_number_gt                 6606
_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 1993)'
_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)+(0.0498P)²+1.3164P] 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        0.0012(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.06(6)
_refine_ls_number_reflns          7818
_refine_ls_number_parameters      443
_refine_ls_number_restraints      25
_refine_ls_R_factor_all           0.0581
_refine_ls_R_factor_gt            0.0432
_refine_ls_wR_factor_ref          0.1045
_refine_ls_wR_factor_gt           0.0973
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.033
_refine_ls_shift/su_max           0.013
_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
H8N H 0.600(3) 0.3708(14) 0.250(4) 0.024(11) Uiso 1 1 d . . .
H5N H 1.159(3) 0.1753(16) -0.024(5) 0.026(13) Uiso 1 1 d . . .
C1 C 0.9224(2) 0.00972(14) -0.0722(4) 0.0347(9) Uani 1 1 d . . .
H1A H 0.8592 0.0155 -0.0534 0.042 Uiso 1 1 calc R . .
H1B H 0.9386 -0.0237 -0.0292 0.042 Uiso 1 1 calc R . .
C2 C 0.9372(3) 0.00735(15) -0.2335(5) 0.0379(9) Uani 1 1 d . . .
H2A H 1.0014 0.0089 -0.2501 0.046 Uiso 1 1 calc R . .
H2B H 0.9172 -0.0267 -0.2668 0.046 Uiso 1 1 calc R . .
C3 C 0.8954(2) 0.04668(14) -0.3295(4) 0.0356(9) Uani 1 1 d . . .
H3A H 0.8947 0.0337 -0.4298 0.043 Uiso 1 1 calc R . .
H3B H 0.8338 0.0519 -0.2988 0.043 Uiso 1 1 calc R . .
C4 C 1.1789(3) 0.23121(15) -0.1298(4) 0.0396(10) Uani 1 1 d . . .
H4A H 1.1611 0.2361 -0.2316 0.048 Uiso 1 1 calc R . .
H4B H 1.2432 0.2260 -0.1275 0.048 Uiso 1 1 calc R . .
C5 C 1.1558(3) 0.27870(16) -0.0442(6) 0.0547(12) Uani 1 1 d . . .
H5A H 1.1755 0.2745 0.0569 0.066 Uiso 1 1 calc R . .
H5B H 1.1867 0.3087 -0.0856 0.066 Uiso 1 1 calc R . .
C6 C 1.0591(4) 0.28777(16) -0.0474(6) 0.0595(13) Uani 1 1 d . . .
H6A H 1.0404 0.2932 -0.1485 0.071 Uiso 1 1 calc R . .
H6B H 1.0457 0.3195 0.0070 0.071 Uiso 1 1 calc R . .
C7 C 0.9142(4) 0.2600(3) 0.0140(8) 0.093(2) Uani 1 1 d U . .
H7A H 0.9033 0.2763 -0.0807 0.111 Uiso 1 1 calc R A 1
H7B H 0.8789 0.2281 0.0157 0.111 Uiso 1 1 calc R A 1
C8 C 0.8831(6) 0.2885(4) 0.1058(11) 0.044(3) Uani 0.443(13) 1 d PU B 1
H8A H 0.8224 0.2982 0.0791 0.053 Uiso 0.443(13) 1 calc PR B 1
H8B H 0.9188 0.3200 0.1134 0.053 Uiso 0.443(13) 1 calc PR B 1
C8' C 0.8617(8) 0.2435(4) 0.1142(12) 0.077(4) Uani 0.557(13) 1 d PU B 2
H8'1 H 0.8573 0.2059 0.1039 0.092 Uiso 0.557(13) 1 calc PR B 2
H8'2 H 0.8026 0.2577 0.0940 0.092 Uiso 0.557(13) 1 calc PR B 2
C9 C 0.8831(4) 0.2551(4) 0.2740(8) 0.121(3) Uani 1 1 d U . .
H9A H 0.8373 0.2283 0.2813 0.146 Uiso 1 1 calc R B 1
H9B H 0.9413 0.2414 0.3019 0.146 Uiso 1 1 calc R B 1
C10 C 0.8577(3) 0.3082(2) 0.3535(5) 0.0531(12) Uani 1 1 d . B .
H10A H 0.8763 0.3070 0.4558 0.064 Uiso 1 1 calc R . .
H10B H 0.8880 0.3372 0.3060 0.064 Uiso 1 1 calc R . .
C11 C 0.7146(3) 0.28973(15) 0.4646(4) 0.0368(9) Uani 1 1 d . B .
H11A H 0.7336 0.3051 0.5571 0.044 Uiso 1 1 calc R . .
H11B H 0.7308 0.2530 0.4664 0.044 Uiso 1 1 calc R . .
C12 C 0.6164(3) 0.29426(14) 0.4522(5) 0.0385(9) Uani 1 1 d . . .
H12A H 0.5967 0.2767 0.3631 0.046 Uiso 1 1 calc R . .
H12B H 0.5886 0.2768 0.5353 0.046 Uiso 1 1 calc R . .
C13 C 0.5866(2) 0.34892(14) 0.4482(4) 0.0309(8) Uani 1 1 d . B .
H13A H 0.5217 0.3501 0.4438 0.037 Uiso 1 1 calc R . .
H13B H 0.6055 0.3665 0.5376 0.037 Uiso 1 1 calc R . .
C14 C 0.8239(3) 0.40128(17) -0.1899(4) 0.0470(11) Uani 1 1 d . . .
H14A H 0.7911 0.3689 -0.1767 0.056 Uiso 1 1 calc R . .
H14B H 0.8703 0.3953 -0.2627 0.056 Uiso 1 1 calc R . .
C15 C 0.7631(3) 0.44177(18) -0.2422(4) 0.0527(13) Uani 1 1 d . . .
H15A H 0.7357 0.4304 -0.3337 0.063 Uiso 1 1 calc R . .
H15B H 0.7969 0.4733 -0.2623 0.063 Uiso 1 1 calc R . .
C16 C 0.6922(3) 0.45350(16) -0.1341(4) 0.0429(10) Uani 1 1 d . . .
H16A H 0.6532 0.4807 -0.1718 0.052 Uiso 1 1 calc R . .
H16B H 0.6564 0.4225 -0.1160 0.052 Uiso 1 1 calc R . .
C17 C 0.8433(2) 0.55847(15) 0.4057(5) 0.0399(10) Uani 1 1 d . . .
H17A H 0.8087 0.5876 0.4437 0.048 Uiso 1 1 calc R . .
H17B H 0.8602 0.5664 0.3050 0.048 Uiso 1 1 calc R . .
C18 C 0.9244(2) 0.55100(14) 0.4963(5) 0.0366(9) Uani 1 1 d . . .
H18A H 0.9073 0.5452 0.5980 0.044 Uiso 1 1 calc R . .
H18B H 0.9609 0.5823 0.4924 0.044 Uiso 1 1 calc R . .
C19 C 0.9774(2) 0.50590(13) 0.4429(5) 0.0348(8) Uani 1 1 d . . .
H19A H 0.9989 0.5130 0.3441 0.042 Uiso 1 1 calc R . .
H19B H 1.0291 0.5009 0.5061 0.042 Uiso 1 1 calc R . .
C20 C 1.0881(3) 0.38057(14) 0.4286(4) 0.0383(9) Uani 1 1 d . . .
H20 H 1.0328 0.3978 0.3965 0.046 Uiso 1 1 calc R . .
N1 N 0.85939(18) 0.11853(11) -0.0893(3) 0.0265(6) Uani 1 1 d . . .
N2 N 0.9823(2) 0.18132(13) -0.2057(3) 0.0405(8) Uani 1 1 d . B .
N3 N 1.00432(19) 0.14357(12) 0.0649(3) 0.0318(7) Uani 1 1 d . B .
N9 N 0.7762(2) 0.41436(12) 0.4068(3) 0.0332(7) Uani 1 1 d . . .
N10 N 0.8562(2) 0.46411(12) 0.1872(3) 0.0350(7) Uani 1 1 d . . .
N11 N 0.7501(2) 0.38293(12) 0.1316(3) 0.0294(7) Uani 1 1 d . . .
O1 O 0.97340(15) 0.05031(10) -0.0015(3) 0.0329(6) Uani 1 1 d . . .
O2 O 0.94150(17) 0.09597(10) -0.3262(3) 0.0354(6) Uani 1 1 d . . .
N5 N 1.1353(2) 0.18609(13) -0.0718(4) 0.0295(7) Uani 1 1 d . B .
N6 N 1.0071(2) 0.24440(13) 0.0157(4) 0.0402(8) Uani 1 1 d . B .
N7 N 0.76193(19) 0.31514(11) 0.3446(3) 0.0283(7) Uani 1 1 d . . .
N8 N 0.6235(2) 0.37544(12) 0.3224(3) 0.0274(7) Uani 1 1 d . . .
O3 O 0.86450(16) 0.41653(10) -0.0517(3) 0.0375(6) Uani 1 1 d . . .
O4 O 0.73370(16) 0.47051(10) 0.0004(3) 0.0329(6) Uani 1 1 d . . .
O5 O 0.79025(15) 0.51193(10) 0.4091(3) 0.0336(6) Uani 1 1 d . . .
O6 O 0.92397(15) 0.45925(8) 0.4421(3) 0.0309(6) Uani 1 1 d . . .
P1 P 0.92907(6) 0.10385(4) 0.03130(10) 0.0274(2) Uani 1 1 d . . .
P2 P 0.90712(6) 0.14117(4) -0.22942(10) 0.0293(2) Uani 1 1 d . . .
P3 P 1.02931(6) 0.18708(3) -0.05010(10) 0.0289(2) Uani 1 1 d . . .
P4 P 0.73046(6) 0.37429(4) 0.29980(9) 0.0252(2) Uani 1 1 d . B .
P5 P 0.83414(6) 0.46021(4) 0.35532(10) 0.0271(2) Uani 1 1 d . . .
P6 P 0.80032(6) 0.43226(4) 0.07563(9) 0.0271(2) Uani 1 1 d . . .
Cl1 Cl 0.85969(7) 0.09190(4) 0.21235(10) 0.0418(2) Uani 1 1 d . . .
Cl2 Cl 0.81199(7) 0.17289(4) -0.35009(12) 0.0451(3) Uani 1 1 d . . .
Cl3 Cl 1.06611(8) 0.34688(5) 0.58825(13) 0.0540(3) Uani 1 1 d . . .
Cl4 Cl 1.16878(7) 0.42793(4) 0.45770(13) 0.0449(2) Uani 1 1 d . . .
Cl5 Cl 1.12222(11) 0.33865(5) 0.29189(15) 0.0721(4) 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 1.468(4) . ?
C1 C2 1.513(6) . ?
C2 C3 1.501(6) . ?
C3 O2 1.467(4) . ?
C4 N5 1.455(5) . ?
C4 C5 1.514(6) . ?
C5 C6 1.493(7) . ?
C6 N6 1.500(6) . ?
C7 C8 1.225(11) . ?
C7 C8' 1.299(14) . ?
C7 N6 1.472(6) . ?
C8 C9 1.786(13) . ?
C8' C9 1.546(12) . ?
C9 C10 1.617(11) . ?
C10 N7 1.472(5) . ?
C11 N7 1.482(5) . ?
C11 C12 1.504(5) . ?
C12 C13 1.499(5) . ?
C13 N8 1.469(5) . ?
C14 O3 1.477(5) . ?
C14 C15 1.487(7) . ?
C15 C16 1.504(6) . ?
C16 O4 1.466(4) . ?
C17 O5 1.460(4) . ?
C17 C18 1.507(5) . ?
C18 C19 1.511(5) . ?
C19 O6 1.465(4) . ?
C20 Cl5 1.753(4) . ?
C20 Cl3 1.754(4) . ?
C20 Cl4 1.764(4) . ?
N1 P1 1.588(3) . ?
N1 P2 1.602(3) . ?
N2 P2 1.568(3) . ?
N2 P3 1.617(3) . ?
N3 P1 1.577(3) . ?
N3 P3 1.604(3) . ?
N9 P5 1.562(3) . ?
N9 P4 1.601(3) . ?
N10 P6 1.576(3) . ?
N10 P5 1.597(3) . ?
N11 P6 1.585(3) . ?
N11 P4 1.603(3) . ?
O1 P1 1.583(3) . ?
O2 P2 1.572(3) . ?
N5 P3 1.627(4) . ?
N6 P3 1.652(4) . ?
N7 P4 1.670(3) . ?
N8 P4 1.643(3) . ?
O3 P6 1.586(3) . ?
O4 P6 1.585(3) . ?
O5 P5 1.588(3) . ?
O6 P5 1.587(2) . ?
P1 Cl1 2.0074(13) . ?
P1 P2 2.6270(13) . ?
P2 Cl2 2.0091(13) . ?
 
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 113.1(3) . . ?
C3 C2 C1 119.6(3) . . ?
O2 C3 C2 112.7(3) . . ?
N5 C4 C5 111.4(3) . . ?
C6 C5 C4 110.4(4) . . ?
C5 C6 N6 113.2(3) . . ?
C8 C7 C8' 57.8(7) . . ?
C8 C7 N6 122.1(7) . . ?
C8' C7 N6 119.5(7) . . ?
C7 C8 C9 108.0(8) . . ?
C7 C8' C9 119.4(9) . . ?
C8' C9 C10 123.6(6) . . ?
C8' C9 C8 42.2(5) . . ?
C10 C9 C8 88.8(5) . . ?
N7 C10 C9 108.5(4) . . ?
N7 C11 C12 113.0(3) . . ?
C13 C12 C11 112.2(3) . . ?
N8 C13 C12 110.6(3) . . ?
O3 C14 C15 110.6(3) . . ?
C14 C15 C16 112.0(3) . . ?
O4 C16 C15 108.6(3) . . ?
O5 C17 C18 109.5(3) . . ?
C17 C18 C19 110.9(3) . . ?
O6 C19 C18 110.7(3) . . ?
Cl5 C20 Cl3 110.7(2) . . ?
Cl5 C20 Cl4 110.0(2) . . ?
Cl3 C20 Cl4 110.9(2) . . ?
P1 N1 P2 110.89(17) . . ?
P2 N2 P3 120.7(2) . . ?
P1 N3 P3 120.48(18) . . ?
P5 N9 P4 123.89(19) . . ?
P6 N10 P5 119.53(18) . . ?
P6 N11 P4 121.53(19) . . ?
C1 O1 P1 119.9(2) . . ?
C3 O2 P2 120.8(2) . . ?
C4 N5 P3 119.0(3) . . ?
C7 N6 C6 107.1(4) . . ?
C7 N6 P3 116.3(4) . . ?
C6 N6 P3 115.6(3) . . ?
C10 N7 C11 112.6(3) . . ?
C10 N7 P4 114.4(3) . . ?
C11 N7 P4 117.5(2) . . ?
C13 N8 P4 118.2(3) . . ?
C14 O3 P6 117.2(2) . . ?
C16 O4 P6 117.3(2) . . ?
C17 O5 P5 118.0(2) . . ?
C19 O6 P5 117.9(2) . . ?
N3 P1 O1 108.02(15) . . ?
N3 P1 N1 117.76(15) . . ?
O1 P1 N1 111.29(15) . . ?
N3 P1 Cl1 108.64(12) . . ?
O1 P1 Cl1 104.35(10) . . ?
N1 P1 Cl1 105.91(12) . . ?
N3 P1 P2 91.72(11) . . ?
O1 P1 P2 101.84(10) . . ?
N1 P1 P2 34.72(10) . . ?
Cl1 P1 P2 139.44(6) . . ?
N2 P2 O2 109.83(18) . . ?
N2 P2 N1 117.67(17) . . ?
O2 P2 N1 109.67(15) . . ?
N2 P2 Cl2 109.18(13) . . ?
O2 P2 Cl2 103.43(11) . . ?
N1 P2 Cl2 106.05(12) . . ?
N2 P2 P1 91.50(12) . . ?
O2 P2 P1 101.76(11) . . ?
N1 P2 P1 34.38(10) . . ?
Cl2 P2 P1 139.19(6) . . ?
N3 P3 N2 114.95(16) . . ?
N3 P3 N5 107.84(17) . . ?
N2 P3 N5 109.13(18) . . ?
N3 P3 N6 110.37(18) . . ?
N2 P3 N6 108.84(17) . . ?
N5 P3 N6 105.27(17) . . ?
N9 P4 N11 115.38(16) . . ?
N9 P4 N8 109.93(17) . . ?
N11 P4 N8 107.87(17) . . ?
N9 P4 N7 109.00(17) . . ?
N11 P4 N7 108.56(16) . . ?
N8 P4 N7 105.65(15) . . ?
N9 P5 O6 108.64(16) . . ?
N9 P5 O5 108.60(16) . . ?
O6 P5 O5 102.55(13) . . ?
N9 P5 N10 117.75(16) . . ?
O6 P5 N10 108.31(16) . . ?
O5 P5 N10 109.90(17) . . ?
N10 P6 O4 107.53(17) . . ?
N10 P6 N11 118.31(16) . . ?
O4 P6 N11 110.35(15) . . ?
N10 P6 O3 106.98(15) . . ?
O4 P6 O3 103.31(15) . . ?
N11 P6 O3 109.28(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.983
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.983
_refine_diff_density_max    0.584
_refine_diff_density_min   -0.389
_refine_diff_density_rms    0.068
