  
data_140825dqp_0m 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H13 F3 I N2 O2' 
_chemical_formula_weight          473.20 
  
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' 
 'I'  'I'  -0.4742   1.8119 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    C2/c 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
  
_cell_length_a                    19.222(8) 
_cell_length_b                    13.042(5) 
_cell_length_c                    14.091(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.239(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      3518(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     8250 
_cell_measurement_theta_min       2.32 
_cell_measurement_theta_max       27.53 
  
_exptl_crystal_description        BLOCK 
_exptl_crystal_colour             COLORLESS 
_exptl_crystal_size_max           0.26 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.787 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1848 
_exptl_absorpt_coefficient_mu     1.866 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.6426 
_exptl_absorpt_correction_T_max   0.6843 
_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             16599 
_diffrn_reflns_av_R_equivalents   0.0237 
_diffrn_reflns_av_sigmaI/netI     0.0191 
_diffrn_reflns_limit_h_min        -24 
_diffrn_reflns_limit_h_max        25 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.44 
_diffrn_reflns_theta_max          27.71 
_reflns_number_total              4086 
_reflns_number_gt                 3446 
_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)+(0.0521P)²+8.9192P] 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          4086 
_refine_ls_number_parameters      237 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0487 
_refine_ls_R_factor_gt            0.0409 
_refine_ls_wR_factor_ref          0.1118 
_refine_ls_wR_factor_gt           0.1051 
_refine_ls_goodness_of_fit_ref    1.004 
_refine_ls_restrained_S_all       1.004 
_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 
I1 I 1.015818(18) 0.11102(2) 0.08827(2) 0.08308(15) Uani 1 1 d . . . 
N1 N 0.89564(12) 0.38791(16) 0.09666(16) 0.0370(5) Uani 1 1 d . . . 
N2 N 0.82763(13) 0.41717(18) 0.08445(17) 0.0414(5) Uani 1 1 d . . . 
F1 F 0.74212(14) 0.6016(2) 0.17320(18) 0.0829(7) Uani 1 1 d . . . 
C17 C 0.82990(16) 0.5178(2) 0.09619(19) 0.0412(6) Uani 1 1 d . . . 
C6 C 1.01500(15) 0.4460(2) 0.12549(18) 0.0436(6) Uani 1 1 d . . . 
C4 C 0.89818(16) 0.5565(2) 0.11367(18) 0.0410(6) Uani 1 1 d . C . 
C5 C 0.94103(15) 0.4689(2) 0.11257(17) 0.0379(5) Uani 1 1 d . . . 
C13 C 0.91456(16) 0.2838(2) 0.09279(18) 0.0410(6) Uani 1 1 d . . . 
F3 F 0.70939(12) 0.5096(2) 0.0535(2) 0.0959(9) Uani 1 1 d . . . 
C3 C 0.9184(2) 0.6643(2) 0.1309(2) 0.0527(7) Uani 1 1 d . . . 
F2 F 0.75846(17) 0.6531(2) 0.0341(2) 0.0981(9) Uani 1 1 d . . . 
C12 C 0.98379(18) 0.2637(2) 0.1053(2) 0.0490(7) Uani 1 1 d . . . 
C14 C 0.85761(18) 0.2079(2) 0.0715(2) 0.0503(7) Uani 1 1 d . . . 
H14 H 0.8493 0.1892 0.0041 0.060 Uiso 1 1 calc R . . 
C15 C 0.8469(2) 0.1219(3) 0.1394(3) 0.0694(11) Uani 1 1 d . . . 
H15A H 0.8352 0.0550 0.1127 0.083 Uiso 1 1 calc R . . 
H15B H 0.8760 0.1208 0.1994 0.083 Uiso 1 1 calc R . . 
C18 C 0.76022(19) 0.5712(3) 0.0894(2) 0.0563(8) Uani 1 1 d . . . 
C11 C 1.03643(17) 0.3424(3) 0.1230(2) 0.0500(7) Uani 1 1 d . . . 
C7 C 1.06616(18) 0.5234(3) 0.1399(2) 0.0591(8) Uani 1 1 d . . . 
H7 H 1.0526 0.5918 0.1405 0.071 Uiso 1 1 calc R . . 
O2 O 0.8691(2) 0.7160(2) 0.1673(3) 0.0976(11) Uani 1 1 d . B . 
C16 C 0.7941(2) 0.2037(3) 0.1251(3) 0.0681(10) Uani 1 1 d . . . 
H16A H 0.7907 0.2526 0.1763 0.082 Uiso 1 1 calc R . . 
H16B H 0.7499 0.1867 0.0896 0.082 Uiso 1 1 calc R . . 
C10 C 1.1084(2) 0.3209(4) 0.1372(3) 0.0703(11) Uani 1 1 d . . . 
H10 H 1.1235 0.2532 0.1358 0.084 Uiso 1 1 calc R . . 
C8 C 1.1358(2) 0.4986(4) 0.1530(3) 0.0739(12) Uani 1 1 d . . . 
H8 H 1.1692 0.5501 0.1621 0.089 Uiso 1 1 calc R . . 
C9 C 1.1562(2) 0.3970(5) 0.1528(3) 0.0823(14) Uani 1 1 d . . . 
H9 H 1.2034 0.3806 0.1634 0.099 Uiso 1 1 calc R . . 
C2 C 0.8786(4) 0.8268(3) 0.1794(4) 0.1067(19) Uani 1 1 d . . . 
H2A H 0.9235 0.8473 0.1594 0.128 Uiso 1 1 calc R A 2 
H2B H 0.8422 0.8632 0.1408 0.128 Uiso 1 1 calc R A 2 
C1 C 0.8751(4) 0.8511(4) 0.2787(5) 0.112(2) Uani 1 1 d . B 2 
H1A H 0.8314 0.8276 0.2987 0.168 Uiso 1 1 calc R B 2 
H1B H 0.8787 0.9240 0.2875 0.168 Uiso 1 1 calc R B 2 
H1C H 0.9128 0.8179 0.3161 0.168 Uiso 1 1 calc R B 2 
O1 O 0.97195(19) 0.7032(2) 0.1112(3) 0.0992(11) Uani 1 1 d . C 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 
I1 C12 2.104(3) . ? 
N1 N2 1.358(3) . ? 
N1 C5 1.375(3) . ? 
N1 C13 1.408(3) . ? 
N2 C17 1.323(4) . ? 
F1 C18 1.322(4) . ? 
C17 C4 1.406(4) . ? 
C17 C18 1.505(4) . ? 
C6 C7 1.411(5) . ? 
C6 C11 1.415(5) . ? 
C6 C5 1.448(4) . ? 
C4 C5 1.409(4) . ? 
C4 C3 1.473(4) . ? 
C13 C12 1.352(4) . ? 
C13 C14 1.486(4) . ? 
F3 C18 1.329(4) . ? 
C3 O1 1.203(5) . ? 
C3 O2 1.305(5) . ? 
F2 C18 1.321(4) . ? 
C12 C11 1.447(5) . ? 
C14 C16 1.494(5) . ? 
C14 C15 1.501(5) . ? 
C14 H14 0.9800 . ? 
C15 C16 1.475(6) . ? 
C15 H15A 0.9700 . ? 
C15 H15B 0.9700 . ? 
C11 C10 1.408(5) . ? 
C7 C8 1.374(6) . ? 
C7 H7 0.9300 . ? 
O2 C2 1.464(4) . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C10 C9 1.357(7) . ? 
C10 H10 0.9300 . ? 
C8 C9 1.381(7) . ? 
C8 H8 0.9300 . ? 
C9 H9 0.9300 . ? 
C2 C1 1.443(8) . ? 
C2 H2A 0.9700 . ? 
C2 H2B 0.9700 . ? 
C1 H1A 0.9600 . ? 
C1 H1B 0.9600 . ? 
C1 H1C 0.9600 . ? 
  
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 
N2 N1 C5 113.2(2) . . ? 
N2 N1 C13 121.0(2) . . ? 
C5 N1 C13 125.8(2) . . ? 
C17 N2 N1 104.0(2) . . ? 
N2 C17 C4 113.4(3) . . ? 
N2 C17 C18 115.6(3) . . ? 
C4 C17 C18 131.0(3) . . ? 
C7 C6 C11 119.1(3) . . ? 
C7 C6 C5 122.3(3) . . ? 
C11 C6 C5 118.6(3) . . ? 
C17 C4 C5 104.2(2) . . ? 
C17 C4 C3 126.8(3) . . ? 
C5 C4 C3 129.1(3) . . ? 
N1 C5 C4 105.2(2) . . ? 
N1 C5 C6 117.6(2) . . ? 
C4 C5 C6 137.2(3) . . ? 
C12 C13 N1 115.9(3) . . ? 
C12 C13 C14 126.5(3) . . ? 
N1 C13 C14 117.5(3) . . ? 
O1 C3 O2 122.7(3) . . ? 
O1 C3 C4 125.7(3) . . ? 
O2 C3 C4 111.6(3) . . ? 
C13 C12 C11 123.3(3) . . ? 
C13 C12 I1 117.6(2) . . ? 
C11 C12 I1 118.9(2) . . ? 
C13 C14 C16 122.9(3) . . ? 
C13 C14 C15 120.7(3) . . ? 
C16 C14 C15 59.0(3) . . ? 
C13 C14 H14 114.4 . . ? 
C16 C14 H14 114.4 . . ? 
C15 C14 H14 114.4 . . ? 
C16 C15 C14 60.3(2) . . ? 
C16 C15 H15A 117.7 . . ? 
C14 C15 H15A 117.7 . . ? 
C16 C15 H15B 117.7 . . ? 
C14 C15 H15B 117.7 . . ? 
H15A C15 H15B 114.9 . . ? 
F1 C18 F2 106.9(3) . . ? 
F1 C18 F3 106.1(3) . . ? 
F2 C18 F3 106.6(3) . . ? 
F1 C18 C17 112.8(3) . . ? 
F2 C18 C17 112.7(3) . . ? 
F3 C18 C17 111.3(3) . . ? 
C10 C11 C6 118.1(4) . . ? 
C10 C11 C12 123.1(3) . . ? 
C6 C11 C12 118.8(3) . . ? 
C8 C7 C6 120.6(4) . . ? 
C8 C7 H7 119.7 . . ? 
C6 C7 H7 119.7 . . ? 
C3 O2 C2 118.0(4) . . ? 
C15 C16 C14 60.7(3) . . ? 
C15 C16 H16A 117.7 . . ? 
C14 C16 H16A 117.7 . . ? 
C15 C16 H16B 117.7 . . ? 
C14 C16 H16B 117.7 . . ? 
H16A C16 H16B 114.8 . . ? 
C9 C10 C11 121.4(4) . . ? 
C9 C10 H10 119.3 . . ? 
C11 C10 H10 119.3 . . ? 
C7 C8 C9 120.0(4) . . ? 
C7 C8 H8 120.0 . . ? 
C9 C8 H8 120.0 . . ? 
C10 C9 C8 120.9(4) . . ? 
C10 C9 H9 119.6 . . ? 
C8 C9 H9 119.6 . . ? 
C1 C2 O2 108.3(5) . . ? 
C1 C2 H2A 110.0 . . ? 
O2 C2 H2A 110.0 . . ? 
C1 C2 H2B 110.0 . . ? 
O2 C2 H2B 110.0 . . ? 
H2A C2 H2B 108.4 . . ? 
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 . . ? 
  
_diffrn_measured_fraction_theta_max    0.989 
_diffrn_reflns_theta_full              27.71 
_diffrn_measured_fraction_theta_full   0.989 
_refine_diff_density_max    0.834 
_refine_diff_density_min   -1.260 
_refine_diff_density_rms    0.115 
