  
data_130914cbp_0m 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H17 F3 N2 O2' 
_chemical_formula_weight          398.38 
  
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                    7.4466(8) 
_cell_length_b                    11.1033(12) 
_cell_length_c                    12.5493(13) 
_cell_angle_alpha                 74.933(5) 
_cell_angle_beta                  73.640(5) 
_cell_angle_gamma                 78.131(5) 
_cell_volume                      951.49(18) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     7742 
_cell_measurement_theta_min       2.29 
_cell_measurement_theta_max       27.65 
  
_exptl_crystal_description        BLOCK 
_exptl_crystal_colour             COLORLESS 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.28 
_exptl_crystal_size_min           0.24 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.390 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              412 
_exptl_absorpt_coefficient_mu     0.110 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.9678 
_exptl_absorpt_correction_T_max   0.9741 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13438 
_diffrn_reflns_av_R_equivalents   0.0439 
_diffrn_reflns_av_sigmaI/netI     0.0327 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          1.92 
_diffrn_reflns_theta_max          27.75 
_reflns_number_total              4390 
_reflns_number_gt                 2829 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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)+(0.1111P)²+0.5281P] 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_number_reflns          4390 
_refine_ls_number_parameters      264 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1102 
_refine_ls_R_factor_gt            0.0792 
_refine_ls_wR_factor_ref          0.2589 
_refine_ls_wR_factor_gt           0.2240 
_refine_ls_goodness_of_fit_ref    1.071 
_refine_ls_restrained_S_all       1.071 
_refine_ls_shift/su_max           0.001 
_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 
C22 C 0.8172(11) 0.5363(7) 0.3904(6) 0.169(3) Uani 1 1 d . . . 
H22A H 0.9130 0.5880 0.3779 0.254 Uiso 1 1 calc R . . 
H22B H 0.8617 0.4508 0.4226 0.254 Uiso 1 1 calc R . . 
H22C H 0.7048 0.5664 0.4419 0.254 Uiso 1 1 calc R . . 
N2 N 0.3867(3) 1.08161(19) 0.30238(18) 0.0537(5) Uani 1 1 d . . . 
N1 N 0.4961(3) 1.0763(2) 0.19696(19) 0.0594(6) Uani 1 1 d . . . 
C16 C 0.3839(4) 0.9646(2) 0.3771(2) 0.0594(7) Uani 1 1 d . . . 
C8 C 0.2893(3) 1.1941(2) 0.3313(2) 0.0536(6) Uani 1 1 d . . . 
C5 C 0.2913(3) 1.3116(2) 0.2426(2) 0.0550(6) Uani 1 1 d . . . 
C9 C 0.1909(4) 1.1877(3) 0.4397(2) 0.0626(7) Uani 1 1 d . . . 
H9 H 0.1250 1.2616 0.4615 0.075 Uiso 1 1 calc R . . 
C15 C 0.2809(4) 0.9592(3) 0.4927(2) 0.0643(7) Uani 1 1 d . . . 
C10 C 0.1828(4) 1.0712(3) 0.5237(2) 0.0664(8) Uani 1 1 d . . . 
C6 C 0.2472(4) 1.3187(3) 0.1408(2) 0.0623(7) Uani 1 1 d . . . 
H6 H 0.2261 1.2464 0.1247 0.075 Uiso 1 1 calc R . . 
C4 C 0.3243(4) 1.4206(3) 0.2629(3) 0.0696(8) Uani 1 1 d . . . 
H4 H 0.3557 1.4180 0.3302 0.084 Uiso 1 1 calc R . . 
C2 C 0.2648(4) 1.5411(3) 0.0838(3) 0.0725(8) Uani 1 1 d . . . 
C7 C 0.2342(4) 1.4322(3) 0.0629(3) 0.0709(8) Uani 1 1 d . . . 
H7 H 0.2041 1.4350 -0.0049 0.085 Uiso 1 1 calc R . . 
C17 C 0.4997(4) 0.8803(3) 0.3127(3) 0.0691(8) Uani 1 1 d . . . 
C3 C 0.3111(5) 1.5336(3) 0.1842(3) 0.0786(9) Uani 1 1 d . . . 
H3 H 0.3340 1.6059 0.1996 0.094 Uiso 1 1 calc R . . 
C11 C 0.0767(5) 1.0695(4) 0.6357(3) 0.0858(10) Uani 1 1 d . . . 
H11 H 0.0096 1.1437 0.6564 0.103 Uiso 1 1 calc R . . 
F3 F 0.6941(4) 1.0059(2) 0.0087(2) 0.1132(8) Uani 1 1 d . . . 
C14 C 0.2751(5) 0.8463(4) 0.5772(3) 0.0874(11) Uani 1 1 d . . . 
H14 H 0.3407 0.7708 0.5586 0.105 Uiso 1 1 calc R . . 
C18 C 0.5646(4) 0.9552(3) 0.2047(3) 0.0667(7) Uani 1 1 d . . . 
F2 F 0.8734(3) 0.8852(3) 0.1094(2) 0.1214(9) Uani 1 1 d . . . 
F1 F 0.6459(4) 0.8168(2) 0.0818(3) 0.1294(10) Uani 1 1 d . . . 
O1 O 0.4254(5) 0.6747(3) 0.3979(3) 0.1316(13) Uani 1 1 d . . . 
C13 C 0.1733(7) 0.8483(5) 0.6858(4) 0.1079(15) Uani 1 1 d . . . 
H13 H 0.1725 0.7739 0.7410 0.129 Uiso 1 1 calc R . . 
C1 C 0.2468(6) 1.6648(3) -0.0014(4) 0.1025(13) Uani 1 1 d . . . 
H1A H 0.1242 1.6813 -0.0172 0.154 Uiso 1 1 calc R . . 
H1B H 0.3425 1.6600 -0.0704 0.154 Uiso 1 1 calc R . . 
H1C H 0.2622 1.7316 0.0294 0.154 Uiso 1 1 calc R . . 
C12 C 0.0725(7) 0.9569(6) 0.7151(3) 0.1038(15) Uani 1 1 d . . . 
H12 H 0.0004 0.9553 0.7891 0.125 Uiso 1 1 calc R . . 
C20 C 0.5408(6) 0.7422(3) 0.3462(4) 0.0960(12) Uani 1 1 d . . . 
O2 O 0.7192(4) 0.7020(2) 0.3080(4) 0.1566(18) Uani 1 1 d . . . 
C19 C 0.6933(5) 0.9152(3) 0.1022(4) 0.0880(10) Uani 1 1 d . . . 
C21 C 0.7787(9) 0.5414(7) 0.2923(6) 0.154(2) Uani 1 1 d . . . 
H21A H 0.6733 0.4998 0.2970 0.184 Uiso 1 1 calc R . . 
H21B H 0.8869 0.5245 0.2309 0.184 Uiso 1 1 calc R . . 
  
  
_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 
C22 C21 1.326(9) . ? 
C22 H22A 0.9600 . ? 
C22 H22B 0.9600 . ? 
C22 H22C 0.9600 . ? 
N2 N1 1.353(3) . ? 
N2 C8 1.390(3) . ? 
N2 C16 1.391(3) . ? 
N1 C18 1.325(3) . ? 
C16 C17 1.394(4) . ? 
C16 C15 1.429(4) . ? 
C8 C9 1.342(4) . ? 
C8 C5 1.479(3) . ? 
C5 C4 1.381(4) . ? 
C5 C6 1.385(4) . ? 
C9 C10 1.440(4) . ? 
C9 H9 0.9300 . ? 
C15 C10 1.396(5) . ? 
C15 C14 1.415(4) . ? 
C10 C11 1.403(4) . ? 
C6 C7 1.384(4) . ? 
C6 H6 0.9300 . ? 
C4 C3 1.386(4) . ? 
C4 H4 0.9300 . ? 
C2 C3 1.376(5) . ? 
C2 C7 1.377(5) . ? 
C2 C1 1.513(4) . ? 
C7 H7 0.9300 . ? 
C17 C18 1.404(4) . ? 
C17 C20 1.472(4) . ? 
C3 H3 0.9300 . ? 
C11 C12 1.381(6) . ? 
C11 H11 0.9300 . ? 
F3 C19 1.332(4) . ? 
C14 C13 1.364(6) . ? 
C14 H14 0.9300 . ? 
C18 C19 1.482(5) . ? 
F2 C19 1.337(4) . ? 
F1 C19 1.319(4) . ? 
O1 C20 1.191(4) . ? 
C13 C12 1.363(7) . ? 
C13 H13 0.9300 . ? 
C1 H1A 0.9600 . ? 
C1 H1B 0.9600 . ? 
C1 H1C 0.9600 . ? 
C12 H12 0.9300 . ? 
C20 O2 1.305(5) . ? 
O2 C21 1.795(8) . ? 
C21 H21A 0.9700 . ? 
C21 H21B 0.9700 . ? 
  
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 
C21 C22 H22A 109.5 . . ? 
C21 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C21 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
N1 N2 C8 122.4(2) . . ? 
N1 N2 C16 113.3(2) . . ? 
C8 N2 C16 124.3(2) . . ? 
C18 N1 N2 103.8(2) . . ? 
N2 C16 C17 104.7(2) . . ? 
N2 C16 C15 118.4(3) . . ? 
C17 C16 C15 136.9(3) . . ? 
C9 C8 N2 116.8(2) . . ? 
C9 C8 C5 123.6(2) . . ? 
N2 C8 C5 119.6(2) . . ? 
C4 C5 C6 118.0(3) . . ? 
C4 C5 C8 120.2(2) . . ? 
C6 C5 C8 121.6(2) . . ? 
C8 C9 C10 122.8(3) . . ? 
C8 C9 H9 118.6 . . ? 
C10 C9 H9 118.6 . . ? 
C10 C15 C14 118.5(3) . . ? 
C10 C15 C16 118.2(2) . . ? 
C14 C15 C16 123.2(3) . . ? 
C15 C10 C11 120.0(3) . . ? 
C15 C10 C9 119.5(3) . . ? 
C11 C10 C9 120.6(3) . . ? 
C5 C6 C7 120.8(3) . . ? 
C5 C6 H6 119.6 . . ? 
C7 C6 H6 119.6 . . ? 
C5 C4 C3 120.8(3) . . ? 
C5 C4 H4 119.6 . . ? 
C3 C4 H4 119.6 . . ? 
C3 C2 C7 118.0(3) . . ? 
C3 C2 C1 121.5(3) . . ? 
C7 C2 C1 120.6(3) . . ? 
C2 C7 C6 121.2(3) . . ? 
C2 C7 H7 119.4 . . ? 
C6 C7 H7 119.4 . . ? 
C16 C17 C18 104.9(2) . . ? 
C16 C17 C20 128.6(3) . . ? 
C18 C17 C20 126.4(3) . . ? 
C2 C3 C4 121.3(3) . . ? 
C2 C3 H3 119.4 . . ? 
C4 C3 H3 119.4 . . ? 
C12 C11 C10 119.6(4) . . ? 
C12 C11 H11 120.2 . . ? 
C10 C11 H11 120.2 . . ? 
C13 C14 C15 120.0(4) . . ? 
C13 C14 H14 120.0 . . ? 
C15 C14 H14 120.0 . . ? 
N1 C18 C17 113.3(3) . . ? 
N1 C18 C19 118.2(3) . . ? 
C17 C18 C19 128.5(3) . . ? 
C12 C13 C14 121.4(4) . . ? 
C12 C13 H13 119.3 . . ? 
C14 C13 H13 119.3 . . ? 
C2 C1 H1A 109.5 . . ? 
C2 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
C2 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C13 C12 C11 120.4(4) . . ? 
C13 C12 H12 119.8 . . ? 
C11 C12 H12 119.8 . . ? 
O1 C20 O2 123.9(3) . . ? 
O1 C20 C17 124.6(4) . . ? 
O2 C20 C17 111.4(3) . . ? 
C20 O2 C21 117.0(3) . . ? 
F1 C19 F3 106.3(3) . . ? 
F1 C19 F2 107.1(3) . . ? 
F3 C19 F2 105.4(3) . . ? 
F1 C19 C18 112.5(3) . . ? 
F3 C19 C18 112.2(3) . . ? 
F2 C19 C18 112.9(3) . . ? 
C22 C21 O2 76.5(6) . . ? 
C22 C21 H21A 115.8 . . ? 
O2 C21 H21A 115.8 . . ? 
C22 C21 H21B 115.8 . . ? 
O2 C21 H21B 115.8 . . ? 
H21A C21 H21B 112.8 . . ? 
  
_diffrn_measured_fraction_theta_max    0.977 
_diffrn_reflns_theta_full              27.76 
_diffrn_measured_fraction_theta_full   0.977 
_refine_diff_density_max    0.385 
_refine_diff_density_min   -0.380 
_refine_diff_density_rms    0.059 
