 
data_s92 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H14 F8 I4 N4 O' 
_chemical_formula_weight          1046.00 
 
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                    25.1399(9) 
_cell_length_b                    4.57150(10) 
_cell_length_c                    25.8949(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.3760(15) 
_cell_angle_gamma                 90.00 
_cell_volume                      2973.47(19) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     7914 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        Needle 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.04 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     2.337 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1936 
_exptl_absorpt_coefficient_mu     4.270 
_exptl_absorpt_correction_type    Empirical 
_exptl_absorpt_correction_T_min   0.3165 
_exptl_absorpt_correction_T_max   0.9195 
_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             8357 
_diffrn_reflns_av_R_equivalents   0.0632 
_diffrn_reflns_av_sigmaI/netI     0.0887 
_diffrn_reflns_limit_h_min        -30 
_diffrn_reflns_limit_h_max        30 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        5 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        31 
_diffrn_reflns_theta_min          3.15 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              2888 
_reflns_number_gt                 1987 
_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)+(0.0026P)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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2888 
_refine_ls_number_parameters      198 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0745 
_refine_ls_R_factor_gt            0.0392 
_refine_ls_wR_factor_ref          0.0606 
_refine_ls_wR_factor_gt           0.0556 
_refine_ls_goodness_of_fit_ref    0.923 
_refine_ls_restrained_S_all       0.923 
_refine_ls_shift/su_max           0.002 
_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 0.507293(18) 0.68898(7) 0.122845(14) 0.03923(15) Uani 1 1 d . . . 
F1 F 0.58449(14) 1.1215(6) 0.06471(11) 0.0402(9) Uani 1 1 d . . . 
F2 F 0.42316(14) 0.6217(6) 0.02748(12) 0.0429(9) Uani 1 1 d . . . 
C1 C 0.5038(3) 0.8702(10) 0.04872(19) 0.0282(15) Uani 1 1 d . . . 
C2 C 0.4619(3) 0.8097(10) 0.0148(2) 0.0320(16) Uani 1 1 d . . . 
C3 C 0.5423(3) 1.0580(10) 0.0333(2) 0.0256(14) Uani 1 1 d . . . 
I2 I 0.308918(16) 0.63958(6) 0.123705(12) 0.02571(12) Uani 1 1 d . . . 
F3 F 0.20640(13) 0.3618(5) 0.06526(11) 0.0348(8) Uani 1 1 d . . . 
F4 F 0.33862(14) 1.0579(6) 0.02823(11) 0.0343(8) Uani 1 1 d . . . 
C11 C 0.2741(2) 0.7071(10) 0.04951(19) 0.0223(13) Uani 1 1 d . . . 
C12 C 0.2287(3) 0.5591(10) 0.0335(2) 0.0267(15) Uani 1 1 d . . . 
C13 C 0.2946(2) 0.9026(10) 0.0151(2) 0.0216(13) Uani 1 1 d . . . 
O1 O 0.5000 0.4857(9) 0.2500 0.0333(15) Uani 1 2 d S . . 
N1 N 0.34089(19) 0.5458(8) 0.23074(15) 0.0250(12) Uani 1 1 d . . . 
N2 N 0.45601(18) 0.0569(8) 0.23588(15) 0.0203(11) Uani 1 1 d . . . 
H2 H 0.4557 -0.1340 0.2402 0.054(19) Uiso 1 1 calc R . . 
C4 C 0.3755(2) 0.3532(9) 0.25190(19) 0.0191(13) Uani 1 1 d . . . 
C5 C 0.3780(2) 0.2907(10) 0.3043(2) 0.0287(15) Uani 1 1 d . . . 
H5 H 0.4029 0.1532 0.3184 0.006(12) Uiso 1 1 calc R . . 
C6 C 0.3426(3) 0.4360(11) 0.3360(2) 0.0336(16) Uani 1 1 d . . . 
H6 H 0.3432 0.3976 0.3721 0.026(14) Uiso 1 1 calc R . . 
C7 C 0.3073(2) 0.6332(11) 0.3147(2) 0.0307(15) Uani 1 1 d . . . 
H7 H 0.2829 0.7326 0.3356 0.049(18) Uiso 1 1 calc R . . 
C8 C 0.3077(2) 0.6850(11) 0.2626(2) 0.0292(15) Uani 1 1 d . . . 
H8 H 0.2835 0.8252 0.2481 0.042(17) Uiso 1 1 calc R . . 
C9 C 0.4091(2) 0.1979(10) 0.21384(19) 0.0244(14) Uani 1 1 d . . . 
H9A H 0.3869 0.0486 0.1956 0.032(15) Uiso 1 1 calc R . . 
H9B H 0.4203 0.3413 0.1878 0.050(17) Uiso 1 1 calc R . . 
C10 C 0.5000 0.2072(15) 0.2500 0.023(2) Uani 1 2 d S . . 
 
 
_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 2.089(5) . ? 
I1 O1 3.4334(12) . ? 
F1 C3 1.342(6) . ? 
F2 C2 1.350(6) . ? 
C1 C3 1.365(7) . ? 
C1 C2 1.371(8) . ? 
C2 C3 1.385(7) 5_675 ? 
C3 C2 1.385(7) 5_675 ? 
I2 C11 2.101(5) . ? 
I2 N1 2.886(4) . ? 
F3 C12 1.358(5) . ? 
F4 C13 1.346(6) . ? 
C11 C12 1.375(7) . ? 
C11 C13 1.378(6) . ? 
C12 C13 1.377(7) 7_565 ? 
C13 C12 1.377(7) 7_565 ? 
O1 C10 1.273(7) . ? 
N1 C4 1.339(6) . ? 
N1 C8 1.357(6) . ? 
N2 C10 1.340(5) . ? 
N2 C9 1.440(6) . ? 
N2 H2 0.8800 . ? 
C4 C5 1.387(6) . ? 
C4 C9 1.503(7) . ? 
C5 C6 1.401(7) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.366(7) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.369(7) . ? 
C7 H7 0.9500 . ? 
C8 H8 0.9500 . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 N2 1.340(5) 2_655 ? 
 
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 O1 170.59(15) . . ? 
C3 C1 C2 118.3(5) . . ? 
C3 C1 I1 120.9(5) . . ? 
C2 C1 I1 120.7(4) . . ? 
F2 C2 C1 121.0(5) . . ? 
F2 C2 C3 117.9(6) . 5_675 ? 
C1 C2 C3 121.1(6) . 5_675 ? 
F1 C3 C1 120.8(5) . . ? 
F1 C3 C2 118.6(5) . 5_675 ? 
C1 C3 C2 120.6(6) . 5_675 ? 
C11 I2 N1 171.53(18) . . ? 
C12 C11 C13 116.9(5) . . ? 
C12 C11 I2 120.9(4) . . ? 
C13 C11 I2 122.2(4) . . ? 
F3 C12 C11 120.1(5) . . ? 
F3 C12 C13 117.8(5) . 7_565 ? 
C11 C12 C13 122.0(5) . 7_565 ? 
F4 C13 C12 118.6(5) . 7_565 ? 
F4 C13 C11 120.4(5) . . ? 
C12 C13 C11 121.0(5) 7_565 . ? 
C10 O1 I1 105.70(7) . . ? 
C4 N1 C8 117.7(4) . . ? 
C4 N1 I2 129.9(3) . . ? 
C8 N1 I2 111.2(3) . . ? 
C10 N2 C9 122.1(4) . . ? 
C10 N2 H2 119.0 . . ? 
C9 N2 H2 119.0 . . ? 
N1 C4 C5 122.5(5) . . ? 
N1 C4 C9 114.6(4) . . ? 
C5 C4 C9 122.8(5) . . ? 
C4 C5 C6 118.1(5) . . ? 
C4 C5 H5 120.9 . . ? 
C6 C5 H5 120.9 . . ? 
C7 C6 C5 119.6(5) . . ? 
C7 C6 H6 120.2 . . ? 
C5 C6 H6 120.2 . . ? 
C6 C7 C8 118.8(6) . . ? 
C6 C7 H7 120.6 . . ? 
C8 C7 H7 120.6 . . ? 
N1 C8 C7 123.2(5) . . ? 
N1 C8 H8 118.4 . . ? 
C7 C8 H8 118.4 . . ? 
N2 C9 C4 115.1(4) . . ? 
N2 C9 H9A 108.5 . . ? 
C4 C9 H9A 108.5 . . ? 
N2 C9 H9B 108.5 . . ? 
C4 C9 H9B 108.5 . . ? 
H9A C9 H9B 107.5 . . ? 
O1 C10 N2 120.9(3) . . ? 
O1 C10 N2 120.9(3) . 2_655 ? 
N2 C10 N2 118.3(6) . 2_655 ? 
 
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 2.07 2.853(5) 147.2 1_545 
 
_diffrn_measured_fraction_theta_max    0.988 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.988 
_refine_diff_density_max    0.924 
_refine_diff_density_min   -0.786 
_refine_diff_density_rms    0.164 
