data_2007src0607
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H19 F6 N2 O P'
_chemical_formula_weight          364.27
 
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'
 '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'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    11.7560(4)
_cell_length_b                    15.6189(3)
_cell_length_c                    18.4464(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3387.05(17)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     4804
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max       27.1
 
_exptl_crystal_description        shard
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.429
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1504
_exptl_absorpt_coefficient_mu     0.225
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9564
_exptl_absorpt_correction_T_max   0.9955
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             44871
_diffrn_reflns_av_R_equivalents   0.0883
_diffrn_reflns_av_sigmaI/netI     0.0713
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          27.12
_reflns_number_total              7443
_reflns_number_gt                 4178
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_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)+(0.0789P)²+0.1162P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.12(13)
_refine_ls_number_reflns          7443
_refine_ls_number_parameters      437
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1229
_refine_ls_R_factor_gt            0.0549
_refine_ls_wR_factor_ref          0.1542
_refine_ls_wR_factor_gt           0.1265
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.011
_refine_ls_shift/su_max           0.008
_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
C16 C 0.1648(4) 0.7097(3) -0.3865(3) 0.0896(15) Uani 1 1 d . . .
H16A H 0.1365 0.7666 -0.3946 0.134 Uiso 1 1 calc R . .
H16B H 0.1630 0.6782 -0.4312 0.134 Uiso 1 1 calc R . .
H16C H 0.2416 0.7127 -0.3690 0.134 Uiso 1 1 calc R . .
C19 C -0.0855(3) 0.7491(2) -0.3217(2) 0.0658(10) Uani 1 1 d . . .
H19A H -0.0626 0.7670 -0.2741 0.099 Uiso 1 1 calc R . .
H19B H -0.1668 0.7432 -0.3231 0.099 Uiso 1 1 calc R . .
H19C H -0.0619 0.7910 -0.3566 0.099 Uiso 1 1 calc R . .
H1N H 0.383(3) 0.661(2) -0.2430(17) 0.049(9) Uiso 1 1 d . . .
H2N H 0.466(3) 0.724(2) -0.274(2) 0.071(11) Uiso 1 1 d . . .
H3N H -0.053(3) 0.541(2) -0.2998(19) 0.063(10) Uiso 1 1 d . . .
H4N H -0.130(3) 0.605(2) -0.259(2) 0.069(11) Uiso 1 1 d . . .
C1 C 0.5397(3) 0.6072(2) -0.25382(18) 0.0513(8) Uani 1 1 d . . .
H1 H 0.5147 0.5535 -0.2316 0.062 Uiso 1 1 calc R . .
C2 C 0.6383(3) 0.6435(2) -0.2104(2) 0.0566(9) Uani 1 1 d . . .
C3 C 0.6706(4) 0.7378(3) -0.1060(2) 0.0864(13) Uani 1 1 d . . .
H3A H 0.7490 0.7256 -0.1161 0.130 Uiso 1 1 calc R . .
H3B H 0.6513 0.7163 -0.0588 0.130 Uiso 1 1 calc R . .
H3C H 0.6586 0.7986 -0.1072 0.130 Uiso 1 1 calc R . .
C4 C 0.4749(3) 0.7072(2) -0.16327(19) 0.0562(9) Uani 1 1 d . . .
C5 C 0.4374(4) 0.7995(2) -0.1571(2) 0.0783(11) Uani 1 1 d . . .
H5A H 0.4508 0.8196 -0.1086 0.118 Uiso 1 1 calc R . .
H5B H 0.3578 0.8038 -0.1680 0.118 Uiso 1 1 calc R . .
H5C H 0.4799 0.8339 -0.1907 0.118 Uiso 1 1 calc R . .
C6 C 0.4165(3) 0.6498(3) -0.1077(2) 0.0747(11) Uani 1 1 d . . .
H6A H 0.4361 0.5911 -0.1170 0.112 Uiso 1 1 calc R . .
H6B H 0.3355 0.6567 -0.1113 0.112 Uiso 1 1 calc R . .
H6C H 0.4411 0.6653 -0.0599 0.112 Uiso 1 1 calc R . .
C7 C 0.5643(3) 0.5919(2) -0.3336(2) 0.0654(10) Uani 1 1 d . . .
H7A H 0.6222 0.5480 -0.3376 0.078 Uiso 1 1 calc R . .
H7B H 0.5951 0.6441 -0.3542 0.078 Uiso 1 1 calc R . .
C8 C 0.4615(3) 0.5647(2) -0.3779(2) 0.0671(10) Uani 1 1 d . . .
C9 C 0.4481(4) 0.5966(3) -0.4472(2) 0.0829(12) Uani 1 1 d . . .
H9 H 0.5015 0.6350 -0.4653 0.099 Uiso 1 1 calc R . .
C10 C 0.3579(5) 0.5732(5) -0.4900(3) 0.1087(18) Uani 1 1 d . . .
H10 H 0.3500 0.5955 -0.5365 0.130 Uiso 1 1 calc R . .
C11 C 0.2808(5) 0.5173(4) -0.4639(4) 0.1024(18) Uani 1 1 d . . .
H11 H 0.2204 0.5006 -0.4933 0.123 Uiso 1 1 calc R . .
C12 C 0.2891(4) 0.4844(3) -0.3950(4) 0.0990(17) Uani 1 1 d . . .
H12 H 0.2340 0.4470 -0.3774 0.119 Uiso 1 1 calc R . .
C13 C 0.3820(4) 0.5079(3) -0.3516(3) 0.0816(13) Uani 1 1 d . . .
H13 H 0.3898 0.4853 -0.3052 0.098 Uiso 1 1 calc R . .
C14 C 0.0331(3) 0.6115(2) -0.22198(17) 0.0478(8) Uani 1 1 d . . .
H14 H 0.0099 0.6588 -0.1904 0.057 Uiso 1 1 calc R . .
C15 C 0.1316(3) 0.6414(2) -0.2680(2) 0.0561(9) Uani 1 1 d . . .
C17 C -0.0309(3) 0.6639(2) -0.33923(18) 0.0524(8) Uani 1 1 d . . .
C18 C -0.0689(4) 0.6278(3) -0.4113(2) 0.0811(12) Uani 1 1 d . . .
H18A H -0.0535 0.6686 -0.4490 0.122 Uiso 1 1 calc R . .
H18B H -0.1491 0.6162 -0.4097 0.122 Uiso 1 1 calc R . .
H18C H -0.0284 0.5757 -0.4211 0.122 Uiso 1 1 calc R . .
C20 C 0.0520(3) 0.5327(2) -0.1754(2) 0.0607(9) Uani 1 1 d . . .
H20A H 0.0666 0.4837 -0.2064 0.073 Uiso 1 1 calc R . .
H20B H 0.1183 0.5414 -0.1450 0.073 Uiso 1 1 calc R . .
C21 C -0.0496(3) 0.5148(2) -0.12859(19) 0.0563(9) Uani 1 1 d . . .
C22 C -0.1300(4) 0.4550(2) -0.1483(2) 0.0732(11) Uani 1 1 d . . .
H22 H -0.1184 0.4209 -0.1890 0.088 Uiso 1 1 calc R . .
C23 C -0.2300(4) 0.4458(3) -0.1068(3) 0.0968(16) Uani 1 1 d . . .
H23 H -0.2845 0.4057 -0.1203 0.116 Uiso 1 1 calc R . .
C24 C -0.2471(5) 0.4951(3) -0.0470(3) 0.0994(17) Uani 1 1 d . . .
H24 H -0.3137 0.4894 -0.0203 0.119 Uiso 1 1 calc R . .
C25 C -0.1658(5) 0.5537(4) -0.0260(3) 0.0985(16) Uani 1 1 d . . .
H25 H -0.1762 0.5862 0.0158 0.118 Uiso 1 1 calc R . .
C26 C -0.0696(4) 0.5636(3) -0.0672(2) 0.0776(11) Uani 1 1 d . . .
H26 H -0.0162 0.6044 -0.0534 0.093 Uiso 1 1 calc R . .
N1 N 0.4531(2) 0.67488(19) -0.23949(16) 0.0504(7) Uani 1 1 d . . .
N2 N 0.5986(2) 0.69663(19) -0.16060(16) 0.0554(7) Uani 1 1 d . . .
N3 N -0.0567(2) 0.59971(18) -0.27935(16) 0.0480(6) Uani 1 1 d . . .
N4 N 0.0931(2) 0.66641(17) -0.33251(17) 0.0556(7) Uani 1 1 d . . .
O1 O 0.7392(2) 0.6245(2) -0.21983(17) 0.0829(9) Uani 1 1 d . . .
O2 O 0.22986(19) 0.6421(2) -0.24520(17) 0.0811(8) Uani 1 1 d . . .
F1 F 0.4703(3) 0.70564(16) 0.1185(2) 0.1257(11) Uani 1 1 d . . .
F2 F 0.4925(2) 0.57631(17) 0.17093(17) 0.1069(9) Uani 1 1 d . . .
F3 F 0.6109(3) 0.68389(17) 0.19859(13) 0.0975(8) Uani 1 1 d . . .
F4 F 0.6700(2) 0.57173(18) 0.13547(17) 0.1087(9) Uani 1 1 d . . .
F5 F 0.6536(3) 0.6996(2) 0.08253(18) 0.1419(13) Uani 1 1 d . . .
F6 F 0.5328(3) 0.59414(17) 0.05378(15) 0.1162(10) Uani 1 1 d . . .
F7 F -0.4722(2) 0.29874(14) -0.13329(16) 0.0941(8) Uani 1 1 d . . .
F8 F -0.5328(3) 0.41296(18) -0.06950(14) 0.1124(10) Uani 1 1 d . . .
F9 F -0.6471(3) 0.29868(19) -0.08242(15) 0.1096(10) Uani 1 1 d . . .
F10 F -0.6884(3) 0.42026(19) -0.14057(17) 0.1161(10) Uani 1 1 d . . .
F11 F -0.6252(2) 0.30541(17) -0.20191(13) 0.0899(8) Uani 1 1 d . . .
F12 F -0.5134(3) 0.42055(16) -0.18920(15) 0.1014(9) Uani 1 1 d . . .
P1 P 0.57013(9) 0.64009(6) 0.12537(5) 0.0639(3) Uani 1 1 d . . .
P2 P -0.58089(9) 0.36044(6) -0.13490(5) 0.0628(3) 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
C16 N4 1.469(4) . ?
C19 C17 1.513(4) . ?
C1 N1 1.491(4) . ?
C1 C7 1.518(5) . ?
C1 C2 1.519(5) . ?
C2 O1 1.235(4) . ?
C2 N2 1.324(4) . ?
C3 N2 1.465(5) . ?
C4 N2 1.465(4) . ?
C4 C5 1.512(5) . ?
C4 N1 1.516(5) . ?
C4 C6 1.525(5) . ?
C7 C8 1.519(5) . ?
C8 C13 1.378(6) . ?
C8 C9 1.381(6) . ?
C9 C10 1.372(7) . ?
C10 C11 1.347(8) . ?
C11 C12 1.376(8) . ?
C12 C13 1.403(6) . ?
C14 N3 1.506(4) . ?
C14 C15 1.510(5) . ?
C14 C20 1.517(5) . ?
C15 O2 1.230(4) . ?
C15 N4 1.331(5) . ?
C17 N4 1.464(4) . ?
C17 C18 1.513(5) . ?
C17 N3 1.522(4) . ?
C20 C21 1.500(5) . ?
C21 C22 1.378(5) . ?
C21 C26 1.386(5) . ?
C22 C23 1.411(6) . ?
C23 C24 1.359(7) . ?
C24 C25 1.379(7) . ?
C25 C26 1.371(6) . ?
F1 P1 1.563(3) . ?
F2 P1 1.591(3) . ?
F3 P1 1.588(3) . ?
F4 P1 1.598(3) . ?
F5 P1 1.566(3) . ?
F6 P1 1.566(3) . ?
F7 P2 1.601(2) . ?
F8 P2 1.564(3) . ?
F9 P2 1.573(3) . ?
F10 P2 1.575(3) . ?
F11 P2 1.593(2) . ?
F12 P2 1.585(3) . ?
 
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
N1 C1 C7 114.4(3) . . ?
N1 C1 C2 99.4(3) . . ?
C7 C1 C2 115.1(3) . . ?
O1 C2 N2 125.9(3) . . ?
O1 C2 C1 124.8(3) . . ?
N2 C2 C1 109.3(3) . . ?
N2 C4 C5 113.2(3) . . ?
N2 C4 N1 99.3(3) . . ?
C5 C4 N1 109.8(3) . . ?
N2 C4 C6 111.0(3) . . ?
C5 C4 C6 112.3(3) . . ?
N1 C4 C6 110.6(3) . . ?
C1 C7 C8 114.5(3) . . ?
C13 C8 C9 118.7(4) . . ?
C13 C8 C7 122.0(4) . . ?
C9 C8 C7 119.3(4) . . ?
C10 C9 C8 121.7(5) . . ?
C11 C10 C9 119.1(5) . . ?
C10 C11 C12 121.7(5) . . ?
C11 C12 C13 119.0(5) . . ?
C8 C13 C12 119.7(5) . . ?
N3 C14 C15 100.4(3) . . ?
N3 C14 C20 113.7(3) . . ?
C15 C14 C20 117.2(3) . . ?
O2 C15 N4 128.5(3) . . ?
O2 C15 C14 122.0(4) . . ?
N4 C15 C14 109.5(3) . . ?
N4 C17 C18 112.3(3) . . ?
N4 C17 C19 112.4(3) . . ?
C18 C17 C19 113.0(3) . . ?
N4 C17 N3 98.9(3) . . ?
C18 C17 N3 109.5(3) . . ?
C19 C17 N3 109.8(3) . . ?
C21 C20 C14 111.1(3) . . ?
C22 C21 C26 118.2(4) . . ?
C22 C21 C20 121.4(3) . . ?
C26 C21 C20 120.3(4) . . ?
C21 C22 C23 119.8(4) . . ?
C24 C23 C22 120.3(5) . . ?
C23 C24 C25 120.2(5) . . ?
C26 C25 C24 119.4(5) . . ?
C25 C26 C21 122.1(5) . . ?
C1 N1 C4 106.6(2) . . ?
C2 N2 C4 113.4(3) . . ?
C2 N2 C3 123.3(3) . . ?
C4 N2 C3 123.2(3) . . ?
C14 N3 C17 106.8(2) . . ?
C15 N4 C17 113.9(3) . . ?
C15 N4 C16 123.1(3) . . ?
C17 N4 C16 121.7(3) . . ?
F1 P1 F6 91.21(17) . . ?
F1 P1 F5 92.3(2) . . ?
F6 P1 F5 91.27(19) . . ?
F1 P1 F3 90.79(16) . . ?
F6 P1 F3 177.95(17) . . ?
F5 P1 F3 89.09(18) . . ?
F1 P1 F2 91.28(17) . . ?
F6 P1 F2 89.87(17) . . ?
F5 P1 F2 176.2(2) . . ?
F3 P1 F2 89.64(16) . . ?
F1 P1 F4 177.64(19) . . ?
F6 P1 F4 89.89(16) . . ?
F5 P1 F4 89.7(2) . . ?
F3 P1 F4 88.09(15) . . ?
F2 P1 F4 86.64(16) . . ?
F8 P2 F9 91.46(17) . . ?
F8 P2 F10 91.72(17) . . ?
F9 P2 F10 90.45(18) . . ?
F8 P2 F12 89.77(16) . . ?
F9 P2 F12 178.44(17) . . ?
F10 P2 F12 90.47(18) . . ?
F8 P2 F11 177.83(17) . . ?
F9 P2 F11 89.14(15) . . ?
F10 P2 F11 90.36(16) . . ?
F12 P2 F11 89.59(15) . . ?
F8 P2 F7 90.74(16) . . ?
F9 P2 F7 90.80(16) . . ?
F10 P2 F7 177.21(17) . . ?
F12 P2 F7 88.22(15) . . ?
F11 P2 F7 87.17(14) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.12
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.242
_refine_diff_density_min   -0.307
_refine_diff_density_rms    0.045
