data_2007src0546
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H16 F6 N P'
_chemical_formula_weight          331.24
 
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'
 
_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                    18.0459(5)
_cell_length_b                    16.9680(5)
_cell_length_c                    9.58230(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.198(2)
_cell_angle_gamma                 90.00
_cell_volume                      2911.00(12)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6753
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.512
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1360
_exptl_absorpt_coefficient_mu     0.247
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9523
_exptl_absorpt_correction_T_max   0.9902
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_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   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             40070
_diffrn_reflns_av_R_equivalents   0.0556
_diffrn_reflns_av_sigmaI/netI     0.0429
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.50
_reflns_number_total              6664
_reflns_number_gt                 4815
_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)+(0.0823P)²+1.8538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          6664
_refine_ls_number_parameters      416
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0825
_refine_ls_R_factor_gt            0.0552
_refine_ls_wR_factor_ref          0.1583
_refine_ls_wR_factor_gt           0.1405
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_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
F7 F 0.3133(2) 0.82674(14) 0.0994(3) 0.0469(9) Uani 0.774(8) 1 d P A 1
F9 F 0.42085(15) 0.88602(19) 0.0690(4) 0.0460(9) Uani 0.774(8) 1 d P A 1
F10 F 0.3596(3) 0.97022(18) -0.0844(3) 0.0489(11) Uani 0.774(8) 1 d P A 1
F12 F 0.25173(14) 0.9118(2) -0.0556(4) 0.0506(11) Uani 0.774(8) 1 d P A 1
F7' F 0.2604(10) 0.8543(8) 0.0633(12) 0.075(6) Uani 0.226(8) 1 d P A 2
F9' F 0.3870(16) 0.8633(12) 0.1331(16) 0.142(12) Uani 0.226(8) 1 d P A 2
F10' F 0.3941(18) 0.9511(19) -0.020(4) 0.214(18) Uani 0.226(8) 1 d P A 2
F12' F 0.2820(15) 0.9495(11) -0.0953(11) 0.108(9) Uani 0.226(8) 1 d P A 2
F8 F 0.34564(9) 0.83854(9) -0.11404(15) 0.0369(4) Uani 1 1 d . A .
F11 F 0.32332(9) 0.96124(9) 0.13419(14) 0.0356(4) Uani 1 1 d . A .
P2 P 0.33511(4) 0.89952(4) 0.01107(6) 0.02573(17) Uani 1 1 d . . .
C14 C 0.27961(14) 0.31866(15) -0.2677(3) 0.0301(5) Uani 1 1 d . . .
H14A H 0.2459 0.2827 -0.2243 0.036 Uiso 1 1 calc R . .
H14B H 0.3098 0.3488 -0.1925 0.036 Uiso 1 1 calc R . .
C15 C 0.32953(15) 0.27295(15) -0.3554(3) 0.0340(6) Uani 1 1 d . . .
H15A H 0.3057 0.2229 -0.3900 0.041 Uiso 1 1 calc R . .
H15B H 0.3784 0.2611 -0.3004 0.041 Uiso 1 1 calc R . .
C16 C 0.33854(14) 0.32881(15) -0.4774(2) 0.0296(5) Uani 1 1 d . . .
H16A H 0.3772 0.3691 -0.4491 0.036 Uiso 1 1 calc R . .
H16B H 0.3524 0.2995 -0.5596 0.036 Uiso 1 1 calc R . .
C17 C 0.26209(13) 0.36644(15) -0.5106(2) 0.0274(5) Uani 1 1 d . . .
H17A H 0.2656 0.4191 -0.5539 0.033 Uiso 1 1 calc R . .
H17B H 0.2282 0.3328 -0.5744 0.033 Uiso 1 1 calc R . .
C18 C 0.18509(12) 0.41955(13) -0.3365(2) 0.0227(5) Uani 1 1 d . . .
H18 H 0.1736 0.4177 -0.2424 0.027 Uiso 1 1 calc R . .
C19 C 0.14432(12) 0.47393(13) -0.4299(2) 0.0224(5) Uani 1 1 d . . .
H19 H 0.1514 0.4751 -0.5265 0.027 Uiso 1 1 calc R . .
C20 C 0.09550(12) 0.52377(13) -0.3800(2) 0.0223(5) Uani 1 1 d . . .
H20 H 0.0888 0.5189 -0.2836 0.027 Uiso 1 1 calc R . .
C21 C 0.05213(12) 0.58444(13) -0.4618(2) 0.0213(4) Uani 1 1 d . . .
C22 C 0.05597(13) 0.59539(14) -0.6056(2) 0.0251(5) Uani 1 1 d . . .
H22 H 0.0881 0.5632 -0.6524 0.030 Uiso 1 1 calc R . .
C23 C 0.01319(14) 0.65288(15) -0.6800(2) 0.0291(5) Uani 1 1 d . . .
H23 H 0.0158 0.6598 -0.7776 0.035 Uiso 1 1 calc R . .
C24 C -0.03383(13) 0.70070(14) -0.6112(3) 0.0279(5) Uani 1 1 d . . .
H24 H -0.0625 0.7408 -0.6619 0.033 Uiso 1 1 calc R . .
C25 C -0.03871(13) 0.68984(14) -0.4698(2) 0.0267(5) Uani 1 1 d . . .
H25 H -0.0712 0.7221 -0.4239 0.032 Uiso 1 1 calc R . .
C26 C 0.00371(12) 0.63193(13) -0.3943(2) 0.0236(5) Uani 1 1 d . . .
H26 H -0.0001 0.6245 -0.2972 0.028 Uiso 1 1 calc R . .
N2 N 0.23643(10) 0.37251(11) -0.36957(18) 0.0215(4) Uani 1 1 d . . .
F1 F 0.06397(11) 0.40218(13) 0.0591(2) 0.0675(6) Uani 1 1 d . B 3
F3 F 0.16097(14) 0.34168(11) -0.02691(19) 0.0717(7) Uani 1 1 d . B 3
F4 F 0.24090(11) 0.40948(12) 0.1212(3) 0.0763(7) Uani 1 1 d . B 3
F6 F 0.15152(14) 0.47209(11) 0.20540(18) 0.0714(7) Uani 1 1 d . B 3
F2 F 0.15164(9) 0.33938(10) 0.20400(15) 0.0429(4) Uani 1 1 d . B 3
F5 F 0.15272(11) 0.47581(9) -0.02744(15) 0.0477(5) Uani 1 1 d . B 3
P1 P 0.15163(4) 0.40751(4) 0.08820(6) 0.02685(17) Uani 1 1 d . B 3
C1 C 0.20798(13) 0.65848(14) 0.1178(2) 0.0245(5) Uani 1 1 d . C 3
H1A H 0.2317 0.7063 0.1628 0.029 Uiso 1 1 calc R C 3
H1B H 0.1939 0.6226 0.1915 0.029 Uiso 1 1 calc R C 3
C2 C 0.14051(14) 0.67953(15) 0.0120(2) 0.0282(5) Uani 1 1 d . C 3
H2A H 0.1121 0.7239 0.0461 0.034 Uiso 1 1 calc R C 3
H2B H 0.1068 0.6337 -0.0077 0.034 Uiso 1 1 calc R C 3
C3 C 0.17659(14) 0.70293(15) -0.1180(2) 0.0277(5) Uani 1 1 d . C 3
H3A H 0.1404 0.6984 -0.2043 0.033 Uiso 1 1 calc R C 3
H3B H 0.1955 0.7577 -0.1098 0.033 Uiso 1 1 calc R C 3
C4 C 0.24073(13) 0.64445(14) -0.1207(2) 0.0256(5) Uani 1 1 d . C 3
H4A H 0.2253 0.5991 -0.1826 0.031 Uiso 1 1 calc R C 3
H4B H 0.2846 0.6701 -0.1537 0.031 Uiso 1 1 calc R C 3
C5 C 0.30642(12) 0.56619(13) 0.0731(2) 0.0201(4) Uani 1 1 d . C 3
H5 H 0.3117 0.5540 0.1706 0.024 Uiso 1 1 calc R C 3
C6 C 0.35316(12) 0.52454(13) -0.0123(2) 0.0210(4) Uani 1 1 d . C 3
H6 H 0.3525 0.5370 -0.1091 0.025 Uiso 1 1 calc R C 3
C7 C 0.39797(12) 0.46731(13) 0.0479(2) 0.0218(5) Uani 1 1 d . C 3
H7 H 0.3974 0.4596 0.1460 0.026 Uiso 1 1 calc R C 3
C8 C 0.44734(12) 0.41580(13) -0.0205(2) 0.0212(4) Uani 1 1 d . C 3
C9 C 0.48683(13) 0.35688(14) 0.0597(3) 0.0268(5) Uani 1 1 d . C 3
H9 H 0.4817 0.3518 0.1568 0.032 Uiso 1 1 calc R C 3
C10 C 0.53355(14) 0.30567(14) -0.0019(3) 0.0304(5) Uani 1 1 d . C 3
H10 H 0.5593 0.2651 0.0527 0.036 Uiso 1 1 calc R C 3
C11 C 0.54251(13) 0.31365(14) -0.1422(3) 0.0283(5) Uani 1 1 d . C 3
H11 H 0.5744 0.2786 -0.1839 0.034 Uiso 1 1 calc R C 3
C12 C 0.50472(13) 0.37315(14) -0.2230(2) 0.0264(5) Uani 1 1 d . C 3
H12 H 0.5115 0.3789 -0.3192 0.032 Uiso 1 1 calc R C 3
C13 C 0.45746(12) 0.42367(14) -0.1632(2) 0.0228(5) Uani 1 1 d . C 3
H13 H 0.4317 0.4639 -0.2186 0.027 Uiso 1 1 calc R C 3
N1 N 0.25778(10) 0.61890(11) 0.02815(17) 0.0188(4) Uani 1 1 d . C 3
 
 
_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
F7 P2 1.575(2) . ?
F9 P2 1.594(3) . ?
F10 P2 1.604(3) . ?
F12 P2 1.573(3) . ?
F7' P2 1.681(9) . ?
F9' P2 1.532(10) . ?
F10' P2 1.436(15) . ?
F12' P2 1.560(12) . ?
F8 P2 1.6128(15) . ?
F11 P2 1.6114(14) . ?
C14 N2 1.485(3) . ?
C14 C15 1.520(4) . ?
C15 C16 1.529(3) . ?
C16 C17 1.517(3) . ?
C17 N2 1.486(3) . ?
C18 N2 1.292(3) . ?
C18 C19 1.425(3) . ?
C19 C20 1.351(3) . ?
C20 C21 1.461(3) . ?
C21 C22 1.400(3) . ?
C21 C26 1.405(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.397(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.392(3) . ?
F1 P1 1.5742(19) . ?
F3 P1 1.5935(18) . ?
F4 P1 1.603(2) . ?
F6 P1 1.5693(17) . ?
F2 P1 1.6024(15) . ?
F5 P1 1.6051(16) . ?
C1 N1 1.480(3) . ?
C1 C2 1.526(3) . ?
C2 C3 1.529(3) . ?
C3 C4 1.527(3) . ?
C4 N1 1.485(3) . ?
C5 N1 1.289(3) . ?
C5 C6 1.434(3) . ?
C6 C7 1.347(3) . ?
C7 C8 1.461(3) . ?
C8 C9 1.400(3) . ?
C8 C13 1.409(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.383(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
F10' P2 F9' 90.2(18) . . ?
F10' P2 F12' 86.9(18) . . ?
F9' P2 F12' 169.7(7) . . ?
F10' P2 F12 122(2) . . ?
F9' P2 F12 145.5(13) . . ?
F12' P2 F12 35.3(10) . . ?
F10' P2 F7 146(2) . . ?
F9' P2 F7 56.3(13) . . ?
F12' P2 F7 127.1(11) . . ?
F12 P2 F7 91.75(18) . . ?
F10' P2 F9 56(2) . . ?
F9' P2 F9 37.1(13) . . ?
F12' P2 F9 142.8(11) . . ?
F12 P2 F9 176.46(16) . . ?
F7 P2 F9 89.84(18) . . ?
F10' P2 F10 33(2) . . ?
F9' P2 F10 123.4(13) . . ?
F12' P2 F10 54.0(11) . . ?
F12 P2 F10 89.3(2) . . ?
F7 P2 F10 176.70(17) . . ?
F9 P2 F10 88.92(18) . . ?
F10' P2 F11 85.6(7) . . ?
F9' P2 F11 80.0(4) . . ?
F12' P2 F11 89.9(4) . . ?
F12 P2 F11 90.23(12) . . ?
F7 P2 F11 92.95(11) . . ?
F9 P2 F11 92.85(14) . . ?
F10 P2 F11 90.17(13) . . ?
F10' P2 F8 94.6(7) . . ?
F9' P2 F8 101.1(4) . . ?
F12' P2 F8 89.0(4) . . ?
F12 P2 F8 88.79(12) . . ?
F7 P2 F8 87.53(11) . . ?
F9 P2 F8 88.12(14) . . ?
F10 P2 F8 89.37(13) . . ?
F11 P2 F8 178.92(9) . . ?
F10' P2 F7' 168.9(9) . . ?
F9' P2 F7' 91.4(12) . . ?
F12' P2 F7' 89.6(11) . . ?
F12 P2 F7' 54.5(7) . . ?
F7 P2 F7' 38.5(6) . . ?
F9 P2 F7' 127.6(7) . . ?
F10 P2 F7' 143.2(7) . . ?
F11 P2 F7' 83.9(3) . . ?
F8 P2 F7' 95.9(3) . . ?
N2 C14 C15 104.42(19) . . ?
C14 C15 C16 103.50(19) . . ?
C17 C16 C15 103.9(2) . . ?
N2 C17 C16 102.56(18) . . ?
N2 C18 C19 125.1(2) . . ?
C20 C19 C18 119.4(2) . . ?
C19 C20 C21 125.5(2) . . ?
C22 C21 C26 119.2(2) . . ?
C22 C21 C20 122.2(2) . . ?
C26 C21 C20 118.6(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C24 119.9(2) . . ?
C25 C24 C23 120.1(2) . . ?
C24 C25 C26 120.4(2) . . ?
C25 C26 C21 119.9(2) . . ?
C18 N2 C14 123.51(19) . . ?
C18 N2 C17 125.51(19) . . ?
C14 N2 C17 110.95(18) . . ?
F6 P1 F1 94.34(14) . . ?
F6 P1 F3 174.03(14) . . ?
F1 P1 F3 91.61(13) . . ?
F6 P1 F2 90.46(10) . . ?
F1 P1 F2 89.67(10) . . ?
F3 P1 F2 89.01(10) . . ?
F6 P1 F4 86.30(14) . . ?
F1 P1 F4 177.61(11) . . ?
F3 P1 F4 87.74(13) . . ?
F2 P1 F4 88.01(10) . . ?
F6 P1 F5 89.49(10) . . ?
F1 P1 F5 91.03(10) . . ?
F3 P1 F5 90.96(9) . . ?
F2 P1 F5 179.30(10) . . ?
F4 P1 F5 91.29(11) . . ?
N1 C1 C2 102.29(17) . . ?
C1 C2 C3 102.49(19) . . ?
C4 C3 C2 104.22(18) . . ?
N1 C4 C3 103.89(17) . . ?
N1 C5 C6 125.16(19) . . ?
C7 C6 C5 118.37(19) . . ?
C6 C7 C8 127.3(2) . . ?
C9 C8 C13 118.8(2) . . ?
C9 C8 C7 118.6(2) . . ?
C13 C8 C7 122.6(2) . . ?
C10 C9 C8 120.4(2) . . ?
C11 C10 C9 120.2(2) . . ?
C10 C11 C12 120.1(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C8 120.3(2) . . ?
C5 N1 C1 123.95(17) . . ?
C5 N1 C4 125.04(18) . . ?
C1 N1 C4 110.91(17) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.783
_refine_diff_density_min   -0.775
_refine_diff_density_rms    0.104
