data_2009src1065

#Dr. P. J. Murphy
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H18 F3 N3 O3'
_chemical_formula_weight          309.29
 
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'
 
_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.9832(6)
_cell_length_b                    8.8773(7)
_cell_length_c                    12.1929(10)
_cell_angle_alpha                 95.866(3)
_cell_angle_beta                  107.215(4)
_cell_angle_gamma                 114.500(4)
_cell_volume                      725.49(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3171
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Blade'
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              324
_exptl_absorpt_coefficient_mu     0.127
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9849
_exptl_absorpt_correction_T_max   0.9937
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 9727 reflections reduced R(int) from 0.0601 to 0.0424
Ratio of minimum to maximum apparent transmission: 0.816499
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_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    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12761
_diffrn_reflns_av_R_equivalents   0.0487
_diffrn_reflns_av_sigmaI/netI     0.0538
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3301
_reflns_number_gt                 2183
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0001P)²+0.8965P] 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          3301
_refine_ls_number_parameters      222
_refine_ls_number_restraints      124
_refine_ls_R_factor_all           0.1279
_refine_ls_R_factor_gt            0.0792
_refine_ls_wR_factor_ref          0.1416
_refine_ls_wR_factor_gt           0.1219
_refine_ls_goodness_of_fit_ref    1.151
_refine_ls_restrained_S_all       1.193
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.4244(4) 0.2482(3) 0.5322(2) 0.0305(6) Uani 1 1 d . . .
C2 C 0.6691(4) 0.3793(4) 0.4599(3) 0.0399(7) Uani 1 1 d . . .
H2A H 0.7117 0.4982 0.4522 0.048 Uiso 1 1 calc R . .
H2B H 0.7032 0.3178 0.4048 0.048 Uiso 1 1 calc R . .
C3 C 0.7655(4) 0.3769(4) 0.5891(3) 0.0347(7) Uani 1 1 d . . .
H3 H 0.8549 0.4969 0.6398 0.042 Uiso 1 1 calc R . .
C4 C 0.8778(5) 0.2735(5) 0.6039(3) 0.0494(9) Uani 1 1 d . . .
H4A H 1.0028 0.3353 0.5908 0.059 Uiso 1 1 calc R . .
H4B H 0.7968 0.1616 0.5438 0.059 Uiso 1 1 calc R . .
C5 C 0.9250(5) 0.2444(5) 0.7283(3) 0.0527(9) Uani 1 1 d . . .
H5A H 0.9961 0.1751 0.7363 0.063 Uiso 1 1 calc R . .
H5B H 1.0123 0.3560 0.7884 0.063 Uiso 1 1 calc R . .
C6 C 0.7341(5) 0.1520(4) 0.7504(3) 0.0466(8) Uani 1 1 d . . .
H6A H 0.7674 0.1354 0.8317 0.056 Uiso 1 1 calc R . .
H6B H 0.6518 0.0373 0.6935 0.056 Uiso 1 1 calc R . .
C7 C 0.6139(4) 0.2501(4) 0.7370(3) 0.0348(7) Uani 1 1 d . . .
H7 H 0.4788 0.1718 0.7343 0.042 Uiso 1 1 calc R . .
C8 C 0.7074(4) 0.4085(4) 0.8405(3) 0.0362(7) Uani 1 1 d . . .
H8A H 0.7408 0.3752 0.9159 0.043 Uiso 1 1 calc R . .
H8B H 0.8331 0.4935 0.8372 0.043 Uiso 1 1 calc R . .
C9 C 0.5787(5) 0.4930(4) 0.8424(3) 0.0409(7) Uani 1 1 d . . .
C10 C 0.6677(5) 0.6527(5) 0.9402(3) 0.0524(9) Uani 1 1 d . . .
H10A H 0.5684 0.6918 0.9363 0.079 Uiso 1 1 calc R . .
H10B H 0.7824 0.7423 0.9310 0.079 Uiso 1 1 calc R . .
H10C H 0.7103 0.6281 1.0173 0.079 Uiso 1 1 calc R . .
N1 N 0.5920(3) 0.2964(3) 0.6237(2) 0.0324(6) Uani 1 1 d . . .
N2 N 0.4575(4) 0.2911(3) 0.4366(2) 0.0401(6) Uani 1 1 d . . .
H2 H 0.3635 0.2691 0.3680 0.048 Uiso 1 1 calc R . .
N3 N 0.2431(3) 0.1646(3) 0.5322(2) 0.0349(6) Uani 1 1 d . . .
H3A H 0.2265 0.1364 0.5967 0.042 Uiso 1 1 calc R . .
H3B H 0.1392 0.1372 0.4676 0.042 Uiso 1 1 calc R . .
O1 O 0.4109(3) 0.4335(3) 0.7697(2) 0.0555(7) Uani 1 1 d . . .
C11 C -0.0525(4) 0.1369(4) 0.2489(3) 0.0333(7) Uani 1 1 d D . .
O11 O 0.1134(3) 0.2274(3) 0.24774(19) 0.0446(6) Uani 1 1 d . A .
O12 O -0.0974(3) 0.0638(3) 0.32452(19) 0.0482(6) Uani 1 1 d . A .
C12 C -0.2358(17) 0.1175(16) 0.1479(10) 0.0463(10) Uani 0.441(10) 1 d PDU A 1
F11 F -0.3441(14) 0.1720(16) 0.1852(5) 0.086(3) Uani 0.441(10) 1 d PDU A 1
F12 F -0.1907(10) 0.1943(14) 0.0672(8) 0.083(3) Uani 0.441(10) 1 d PDU A 1
F13 F -0.3638(18) -0.0435(12) 0.0938(10) 0.081(4) Uani 0.441(10) 1 d PDU A 1
C212 C -0.2217(14) 0.1185(13) 0.1387(8) 0.0463(10) Uani 0.559(10) 1 d PDU A 2
F211 F -0.2359(11) 0.2600(8) 0.1443(8) 0.102(3) Uani 0.559(10) 1 d PDU A 2
F212 F -0.1949(10) 0.0877(13) 0.0386(5) 0.091(2) Uani 0.559(10) 1 d PDU A 2
F213 F -0.3920(11) -0.0103(12) 0.1200(8) 0.092(3) Uani 0.559(10) 1 d PDU A 2
 
 
_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 N3 1.324(3) . ?
C1 N1 1.327(4) . ?
C1 N2 1.328(4) . ?
C2 N2 1.456(4) . ?
C2 C3 1.542(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.481(3) . ?
C3 C4 1.517(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.528(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.523(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.463(3) . ?
C7 C8 1.528(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.506(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.214(4) . ?
C9 C10 1.502(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N2 H2 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C11 O12 1.234(3) . ?
C11 O11 1.237(3) . ?
C11 C212 1.535(9) . ?
C11 C12 1.540(11) . ?
C12 F13 1.311(11) . ?
C12 F11 1.312(12) . ?
C12 F12 1.305(11) . ?
C212 F213 1.297(9) . ?
C212 F211 1.305(10) . ?
C212 F212 1.321(10) . ?
 
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
N3 C1 N1 125.6(3) . . ?
N3 C1 N2 122.4(3) . . ?
N1 C1 N2 112.0(2) . . ?
N2 C2 C3 103.3(2) . . ?
N2 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N2 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
N1 C3 C4 109.7(2) . . ?
N1 C3 C2 102.5(2) . . ?
C4 C3 C2 114.9(3) . . ?
N1 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C3 C4 C5 110.5(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 110.1(3) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 112.5(3) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N1 C7 C8 111.1(2) . . ?
N1 C7 C6 108.4(2) . . ?
C8 C7 C6 112.6(2) . . ?
N1 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C6 C7 H7 108.2 . . ?
C9 C8 C7 114.7(2) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 C10 121.9(3) . . ?
O1 C9 C8 121.7(3) . . ?
C10 C9 C8 116.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C7 127.3(2) . . ?
C1 N1 C3 110.6(2) . . ?
C7 N1 C3 120.9(2) . . ?
C1 N2 C2 111.3(2) . . ?
C1 N2 H2 124.3 . . ?
C2 N2 H2 124.3 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
O12 C11 O11 129.6(3) . . ?
O12 C11 C212 117.8(4) . . ?
O11 C11 C212 112.6(4) . . ?
O12 C11 C12 112.1(5) . . ?
O11 C11 C12 118.2(5) . . ?
C212 C11 C12 6.7(8) . . ?
F13 C12 F11 101.7(9) . . ?
F13 C12 F12 107.6(11) . . ?
F11 C12 F12 108.4(10) . . ?
F13 C12 C11 112.2(10) . . ?
F11 C12 C11 113.4(8) . . ?
F12 C12 C11 112.8(8) . . ?
F213 C212 F211 110.3(9) . . ?
F213 C212 F212 102.8(8) . . ?
F211 C212 F212 105.6(8) . . ?
F213 C212 C11 113.9(8) . . ?
F211 C212 C11 110.7(7) . . ?
F212 C212 C11 113.1(7) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N2 H2 O11  0.88 1.95 2.805(3) 162.4 .
N3 H3B O12  0.88 1.96 2.836(3) 177.0 .
N3 H3A O12  0.88 2.14 2.914(3) 147.1 2_556
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.319
_refine_diff_density_min   -0.254
_refine_diff_density_rms    0.052
