 
data_s92 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19 H14 F4 I2 N4 O' 
_chemical_formula_weight          644.14 
 
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
_symmetry_space_group_name_hall   '-C 2yc'
 
 
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                    31.7811(10) 
_cell_length_b                    4.52810(10) 
_cell_length_c                    14.8008(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  99.8140(11) 
_cell_angle_gamma                 90.00 
_cell_volume                      2098.78(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     4841 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        Prism 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     2.039 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1224 
_exptl_absorpt_coefficient_mu     3.050 
_exptl_absorpt_correction_type    Empirical 
_exptl_absorpt_correction_T_min   0.6576 
_exptl_absorpt_correction_T_max   0.7924 
_exptl_absorpt_process_details    'SORTAV (R. H. Blessing, 1995, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             6786 
_diffrn_reflns_av_R_equivalents   0.0468 
_diffrn_reflns_av_sigmaI/netI     0.0392 
_diffrn_reflns_limit_h_min        -38 
_diffrn_reflns_limit_h_max        38 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          3.28 
_diffrn_reflns_theta_max          25.99 
_reflns_number_total              1955 
_reflns_number_gt                 1721 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0493P)²+0.0000P] 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      SHELXL 
_refine_ls_extinction_coef        0.0053(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          1955 
_refine_ls_number_parameters      145 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0333 
_refine_ls_R_factor_gt            0.0288 
_refine_ls_wR_factor_ref          0.0737 
_refine_ls_wR_factor_gt           0.0712 
_refine_ls_goodness_of_fit_ref    0.980 
_refine_ls_restrained_S_all       0.980 
_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 0.179032(6) -0.01726(4) 0.304774(13) 0.02315(14) Uani 1 1 d . . . 
F1 F 0.27772(5) 0.1342(4) 0.38261(11) 0.0378(5) Uani 1 1 d . . . 
F2 F 0.16862(6) -0.4551(3) 0.46995(13) 0.0313(5) Uani 1 1 d . . . 
C1 C 0.22141(8) -0.1560(6) 0.42133(18) 0.0232(6) Uani 1 1 d . . . 
C2 C 0.26333(10) -0.0571(6) 0.4398(2) 0.0252(7) Uani 1 1 d . . . 
C3 C 0.20905(8) -0.3508(6) 0.48322(18) 0.0226(6) Uani 1 1 d . . . 
O1 O 0.0000 0.1349(5) 0.2500 0.0282(7) Uani 1 2 d S . . 
N1 N 0.11421(7) 0.1115(6) 0.14673(16) 0.0258(5) Uani 1 1 d . . . 
N2 N 0.03448(8) 0.5673(5) 0.23591(18) 0.0229(5) Uani 1 1 d . . . 
H2 H 0.0324 0.7600 0.2287 0.049(10) Uiso 1 1 calc R . . 
C4 C 0.07838(8) 0.2684(5) 0.14384(17) 0.0200(6) Uani 1 1 d . . . 
C5 C 0.04760(9) 0.2830(6) 0.06564(19) 0.0301(7) Uani 1 1 d . . . 
H5 H 0.0223 0.3945 0.0654 0.038(8) Uiso 1 1 calc R . . 
C6 C 0.05418(10) 0.1335(7) -0.0122(2) 0.0363(7) Uani 1 1 d . . . 
H6 H 0.0337 0.1421 -0.0669 0.056(10) Uiso 1 1 calc R . . 
C7 C 0.09068(13) -0.0263(6) -0.0087(3) 0.0355(9) Uani 1 1 d . . . 
H7 H 0.0958 -0.1334 -0.0609 0.044(9) Uiso 1 1 calc R . . 
C8 C 0.12004(12) -0.0314(6) 0.0709(3) 0.0342(8) Uani 1 1 d . . . 
H8 H 0.1456 -0.1414 0.0721 0.037(8) Uiso 1 1 calc R . . 
C9 C 0.07473(9) 0.4215(6) 0.2327(2) 0.0236(6) Uani 1 1 d . . . 
H9A H 0.0797 0.2735 0.2827 0.036(8) Uiso 1 1 calc R . . 
H9B H 0.0978 0.5702 0.2455 0.035(9) Uiso 1 1 calc R . . 
C10 C 0.0000 0.4090(9) 0.2500 0.0206(8) Uani 1 2 d S . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
I1 0.01785(19) 0.0268(2) 0.02302(19) 0.00103(6) -0.00151(11) 0.00279(6) 
F1 0.0266(10) 0.0473(11) 0.0378(11) 0.0191(8) 0.0004(8) -0.0104(8) 
F2 0.0152(10) 0.0401(10) 0.0363(12) 0.0062(7) -0.0023(8) -0.0085(7) 
C1 0.0175(14) 0.0259(16) 0.0245(15) -0.0008(10) -0.0009(11) 0.0008(10) 
C2 0.0221(17) 0.0239(14) 0.0303(18) 0.0071(12) 0.0062(14) -0.0001(12) 
C3 0.0128(14) 0.0256(16) 0.0280(16) -0.0036(11) -0.0010(11) -0.0045(10) 
O1 0.0292(16) 0.0089(16) 0.0481(19) 0.000 0.0112(13) 0.000 
N1 0.0191(13) 0.0320(14) 0.0257(14) -0.0012(11) 0.0019(10) 0.0066(11) 
N2 0.0165(13) 0.0157(11) 0.0376(15) -0.0002(11) 0.0080(11) 0.0003(10) 
C4 0.0161(14) 0.0209(13) 0.0219(14) 0.0034(10) 0.0003(11) -0.0011(10) 
C5 0.0192(16) 0.0386(17) 0.0304(17) 0.0052(12) -0.0019(13) 0.0075(12) 
C6 0.0302(19) 0.053(2) 0.0218(17) 0.0035(14) -0.0060(13) 0.0000(15) 
C7 0.028(2) 0.050(2) 0.030(2) -0.0070(13) 0.0109(17) -0.0012(13) 
C8 0.027(2) 0.047(2) 0.028(2) -0.0066(12) 0.0060(16) 0.0106(12) 
C9 0.0163(15) 0.0260(13) 0.0280(17) -0.0012(12) 0.0021(12) 0.0020(12) 
C10 0.018(2) 0.020(2) 0.024(2) 0.000 0.0041(16) 0.000 
 
_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 C1 2.096(3) . ? 
I1 N1 2.900(2) . ? 
F1 C2 1.345(3) . ? 
F2 C3 1.351(3) . ? 
C1 C3 1.376(4) . ? 
C1 C2 1.388(4) . ? 
C2 C3 1.378(4) 7_546 ? 
C3 C2 1.378(4) 7_546 ? 
O1 C10 1.241(5) . ? 
N1 C8 1.335(4) . ? 
N1 C4 1.337(3) . ? 
N2 C10 1.355(3) . ? 
N2 C9 1.448(4) . ? 
N2 H2 0.8800 . ? 
C4 C5 1.384(4) . ? 
C4 C9 1.509(4) . ? 
C5 C6 1.382(4) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.361(5) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.373(6) . ? 
C7 H7 0.9500 . ? 
C8 H8 0.9500 . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 N2 1.355(3) 2 ? 
 
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 
C1 I1 N1 172.99(9) . . ? 
C3 C1 C2 116.7(2) . . ? 
C3 C1 I1 121.58(19) . . ? 
C2 C1 I1 121.8(2) . . ? 
F1 C2 C3 118.6(3) . 7_546 ? 
F1 C2 C1 120.1(3) . . ? 
C3 C2 C1 121.3(3) 7_546 . ? 
F2 C3 C1 120.0(2) . . ? 
F2 C3 C2 118.0(2) . 7_546 ? 
C1 C3 C2 122.0(2) . 7_546 ? 
C8 N1 C4 118.0(3) . . ? 
C8 N1 I1 113.5(2) . . ? 
C4 N1 I1 128.09(17) . . ? 
C10 N2 C9 120.4(3) . . ? 
C10 N2 H2 119.8 . . ? 
C9 N2 H2 119.8 . . ? 
N1 C4 C5 122.0(3) . . ? 
N1 C4 C9 114.1(2) . . ? 
C5 C4 C9 124.0(2) . . ? 
C6 C5 C4 119.2(3) . . ? 
C6 C5 H5 120.4 . . ? 
C4 C5 H5 120.4 . . ? 
C7 C6 C5 118.6(3) . . ? 
C7 C6 H6 120.7 . . ? 
C5 C6 H6 120.7 . . ? 
C6 C7 C8 119.5(3) . . ? 
C6 C7 H7 120.3 . . ? 
C8 C7 H7 120.3 . . ? 
N1 C8 C7 122.8(3) . . ? 
N1 C8 H8 118.6 . . ? 
C7 C8 H8 118.6 . . ? 
N2 C9 C4 116.0(2) . . ? 
N2 C9 H9A 108.3 . . ? 
C4 C9 H9A 108.3 . . ? 
N2 C9 H9B 108.3 . . ? 
C4 C9 H9B 108.3 . . ? 
H9A C9 H9B 107.4 . . ? 
O1 C10 N2 121.95(19) . . ? 
O1 C10 N2 121.95(19) . 2 ? 
N2 C10 N2 116.1(4) . 2 ? 
 
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 O1  0.88 2.04 2.815(3) 146.8 1_565 
 
_diffrn_measured_fraction_theta_max    0.947 
_diffrn_reflns_theta_full              25.99 
_diffrn_measured_fraction_theta_full   0.947 
_refine_diff_density_max    1.264 
_refine_diff_density_min   -1.123 
_refine_diff_density_rms    0.132 
