data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Davies / Shaw
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H16 Cl F8 N4 O4 P3'
_chemical_formula_weight          560.65
 
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'
 'F'  'F'   0.0171   0.0103
 '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            Orthorhombic
_symmetry_space_group_name_H-M    Cmc2(1)
_symmetry_space_group_name_hall   'C 2c -2'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x, -y, z+1/2'
 '-x, y, z'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1/2, z+1/2'
 'x+1/2, -y+1/2, z+1/2'
 '-x+1/2, y+1/2, z'
 
_cell_length_a                    20.1599(10)
_cell_length_b                    11.7656(6)
_cell_length_c                    8.7964(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2086.45(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     6314
_cell_measurement_theta_min       5.11
_cell_measurement_theta_max       23.24
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.785
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1128
_exptl_absorpt_coefficient_mu     0.513
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9410
_exptl_absorpt_correction_T_max   0.9848
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             6431
_diffrn_reflns_av_R_equivalents   0.0488
_diffrn_reflns_av_sigmaI/netI     0.0605
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          27.44
_reflns_number_total              2027
_reflns_number_gt                 1689
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0569P)²+0.8327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_number_reflns          2027
_refine_ls_number_parameters      152
_refine_ls_number_restraints      7
_refine_ls_R_factor_all           0.0568
_refine_ls_R_factor_gt            0.0413
_refine_ls_wR_factor_ref          0.1053
_refine_ls_wR_factor_gt           0.0967
_refine_ls_goodness_of_fit_ref    1.010
_refine_ls_restrained_S_all       1.008
_refine_ls_shift/su_max           0.009
_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 0.32313(18) 0.3044(3) 0.0739(5) 0.0351(9) Uani 1 1 d . . .
H1A H 0.3106 0.3856 0.0693 0.042 Uiso 1 1 calc R . .
H1B H 0.3099 0.2743 0.1746 0.042 Uiso 1 1 calc R . .
C2 C 0.28800(19) 0.2399(4) -0.0492(5) 0.0383(10) Uani 1 1 d . . .
C3 C 0.2924(2) 0.1094(4) -0.0412(5) 0.0388(9) Uani 1 1 d . . .
C4 C 0.3617(2) 0.0597(4) -0.0248(5) 0.0397(10) Uani 1 1 d . . .
H4A H 0.3603 -0.0239 -0.0376 0.048 Uiso 1 1 calc R . .
H4B H 0.3915 0.0918 -0.1033 0.048 Uiso 1 1 calc R . .
C5 C 0.4400(2) 0.3824(4) 0.5967(5) 0.0515(12) Uani 1 1 d . . .
H5A H 0.4090 0.4261 0.5320 0.062 Uiso 1 1 calc R . .
H5B H 0.4169 0.3142 0.6359 0.062 Uiso 1 1 calc R . .
C6 C 0.4646(3) 0.4525(8) 0.7218(10) 0.120(3) Uani 1 1 d U . .
H6A H 0.4481 0.5313 0.7103 0.143 Uiso 1 1 calc R . .
H6B H 0.4481 0.4222 0.8197 0.143 Uiso 1 1 calc R . .
N1 N 0.5000 0.1850(4) 0.0591(6) 0.0330(11) Uani 1 2 d S . .
N2 N 0.43235(15) 0.2200(3) 0.3215(4) 0.0341(8) Uani 1 1 d . . .
N3 N 0.5000 0.3500(4) 0.5101(5) 0.0357(11) Uani 1 2 d S . .
F1 F 0.31260(13) 0.2711(2) -0.1881(3) 0.0503(7) Uani 1 1 d . . .
F2 F 0.22297(11) 0.2698(2) -0.0499(3) 0.0493(7) Uani 1 1 d . . .
F3 F 0.25367(11) 0.0764(2) 0.0765(3) 0.0478(6) Uani 1 1 d . . .
F4 F 0.26478(13) 0.0653(2) -0.1695(3) 0.0580(8) Uani 1 1 d . . .
P1 P 0.43196(4) 0.19687(8) 0.14557(13) 0.0286(2) Uani 1 1 d . . .
P2 P 0.5000 0.23338(11) 0.41213(16) 0.0290(3) Uani 1 2 d S . .
Cl1 Cl 0.5000 0.10720(12) 0.57319(19) 0.0451(4) Uani 1 2 d S . .
O1 O 0.39320(12) 0.2930(2) 0.0549(3) 0.0353(7) Uani 1 1 d . . .
O2 O 0.38542(11) 0.0882(2) 0.1241(3) 0.0337(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 O1 1.429(4) . ?
C1 C2 1.500(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 F2 1.357(4) . ?
C2 F1 1.368(5) . ?
C2 C3 1.540(6) . ?
C3 F3 1.353(5) . ?
C3 F4 1.360(5) . ?
C3 C4 1.522(6) . ?
C4 O2 1.434(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.462(8) . ?
C5 N3 1.479(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C6 1.426(13) 4_655 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N1 P1 1.575(3) . ?
N1 P1 1.575(3) 4_655 ?
N2 P1 1.571(4) . ?
N2 P2 1.588(3) . ?
N3 C5 1.479(5) 4_655 ?
N3 P2 1.620(5) . ?
P1 O1 1.589(3) . ?
P1 O2 1.597(3) . ?
P2 N2 1.588(3) 4_655 ?
P2 Cl1 2.052(2) . ?
 
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 109.6(3) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
F2 C2 F1 106.1(3) . . ?
F2 C2 C1 109.2(3) . . ?
F1 C2 C1 109.7(3) . . ?
F2 C2 C3 108.3(3) . . ?
F1 C2 C3 106.7(3) . . ?
C1 C2 C3 116.4(3) . . ?
F3 C3 F4 106.8(3) . . ?
F3 C3 C4 110.3(3) . . ?
F4 C3 C4 107.9(3) . . ?
F3 C3 C2 106.8(3) . . ?
F4 C3 C2 108.6(3) . . ?
C4 C3 C2 116.1(3) . . ?
O2 C4 C3 107.6(3) . . ?
O2 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O2 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 N3 104.9(4) . . ?
C6 C5 H5A 110.8 . . ?
N3 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
N3 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C6 C6 C5 109.8(3) 4_655 . ?
C6 C6 H6A 109.7 4_655 . ?
C5 C6 H6A 109.7 . . ?
C6 C6 H6B 109.7 4_655 . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
P1 N1 P1 121.2(3) . 4_655 ?
P1 N2 P2 121.1(2) . . ?
C5 N3 C5 109.6(5) 4_655 . ?
C5 N3 P2 119.5(3) 4_655 . ?
C5 N3 P2 119.5(3) . . ?
N2 P1 N1 119.1(2) . . ?
N2 P1 O1 111.94(17) . . ?
N1 P1 O1 104.4(2) . . ?
N2 P1 O2 104.97(17) . . ?
N1 P1 O2 112.53(18) . . ?
O1 P1 O2 102.79(14) . . ?
N2 P2 N2 118.4(3) . 4_655 ?
N2 P2 N3 110.55(14) . . ?
N2 P2 N3 110.55(14) 4_655 . ?
N2 P2 Cl1 105.96(14) . . ?
N2 P2 Cl1 105.96(14) 4_655 . ?
N3 P2 Cl1 104.21(19) . . ?
C1 O1 P1 119.6(3) . . ?
C4 O2 P1 119.4(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 F2 -167.4(3) . . . . ?
O1 C1 C2 F1 -51.6(4) . . . . ?
O1 C1 C2 C3 69.7(5) . . . . ?
F2 C2 C3 F3 -51.2(4) . . . . ?
F1 C2 C3 F3 -165.0(3) . . . . ?
C1 C2 C3 F3 72.1(4) . . . . ?
F2 C2 C3 F4 63.6(4) . . . . ?
F1 C2 C3 F4 -50.2(4) . . . . ?
C1 C2 C3 F4 -173.0(3) . . . . ?
F2 C2 C3 C4 -174.6(3) . . . . ?
F1 C2 C3 C4 71.6(4) . . . . ?
C1 C2 C3 C4 -51.3(5) . . . . ?
F3 C3 C4 O2 -52.5(4) . . . . ?
F4 C3 C4 O2 -168.8(3) . . . . ?
C2 C3 C4 O2 69.1(5) . . . . ?
N3 C5 C6 C6 -6.1(5) . . . 4_655 ?
C6 C5 N3 C5 10.0(8) . . . 4_655 ?
C6 C5 N3 P2 153.4(5) . . . . ?
P2 N2 P1 N1 1.0(4) . . . . ?
P2 N2 P1 O1 -121.2(2) . . . . ?
P2 N2 P1 O2 128.1(2) . . . . ?
P1 N1 P1 N2 -0.5(4) 4_655 . . . ?
P1 N1 P1 O1 125.3(3) 4_655 . . . ?
P1 N1 P1 O2 -124.0(3) 4_655 . . . ?
P1 N2 P2 N2 -1.4(4) . . . 4_655 ?
P1 N2 P2 N3 127.6(3) . . . . ?
P1 N2 P2 Cl1 -120.1(2) . . . . ?
C5 N3 P2 N2 -176.6(4) 4_655 . . . ?
C5 N3 P2 N2 43.5(4) . . . . ?
C5 N3 P2 N2 -43.5(4) 4_655 . . 4_655 ?
C5 N3 P2 N2 176.6(4) . . . 4_655 ?
C5 N3 P2 Cl1 69.9(4) 4_655 . . . ?
C5 N3 P2 Cl1 -69.9(4) . . . . ?
C2 C1 O1 P1 -94.9(4) . . . . ?
N2 P1 O1 C1 -67.3(3) . . . . ?
N1 P1 O1 C1 162.5(3) . . . . ?
O2 P1 O1 C1 44.9(3) . . . . ?
C3 C4 O2 P1 -96.5(3) . . . . ?
N2 P1 O2 C4 165.5(3) . . . . ?
N1 P1 O2 C4 -63.5(3) . . . . ?
O1 P1 O2 C4 48.3(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.44
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.405
_refine_diff_density_min   -0.394
_refine_diff_density_rms    0.072
