data_03src0204
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H10 F4 I2 N2 O2 S'
_chemical_formula_weight          588.09
 
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'
 'S'  'S'   0.1246   0.1234
 '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'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pbca
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    21.0514(3)
_cell_length_b                    7.02760(10)
_cell_length_c                    24.2942(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3594.10(8)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     28956
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     2.174
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2208
_exptl_absorpt_coefficient_mu     3.663
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.3220
_exptl_absorpt_correction_T_max   0.5918
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(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             24478
_diffrn_reflns_av_R_equivalents   0.0783
_diffrn_reflns_av_sigmaI/netI     0.0399
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        27
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          3.17
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4114
_reflns_number_gt                 3747
_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)+(0.0363P)²+7.7112P] 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        0.00288(14)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4114
_refine_ls_number_parameters      220
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0369
_refine_ls_R_factor_gt            0.0322
_refine_ls_wR_factor_ref          0.0785
_refine_ls_wR_factor_gt           0.0761
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_restrained_S_all       1.083
_refine_ls_shift/su_max           0.003
_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 0.23938(16) 0.0064(5) 0.07691(12) 0.0145(6) Uani 1 1 d . . .
C2 C 0.20040(16) -0.0489(5) 0.03356(14) 0.0166(7) Uani 1 1 d . . .
C3 C 0.22579(18) -0.1002(5) -0.01666(13) 0.0164(7) Uani 1 1 d . . .
C4 C 0.29029(18) -0.1003(5) -0.02606(14) 0.0166(7) Uani 1 1 d . . .
C5 C 0.32915(17) -0.0451(5) 0.01721(14) 0.0170(7) Uani 1 1 d . . .
C6 C 0.30399(16) 0.0072(5) 0.06756(13) 0.0152(6) Uani 1 1 d . . .
C7 C 0.39458(16) -0.4215(5) -0.25845(13) 0.0154(7) Uani 1 1 d . . .
C8 C 0.32323(19) -0.6563(6) -0.21287(17) 0.0251(8) Uani 1 1 d . . .
H8A H 0.3207 -0.5713 -0.1810 0.038 Uiso 1 1 calc R . .
H8B H 0.3286 -0.7878 -0.2002 0.038 Uiso 1 1 calc R . .
H8C H 0.2841 -0.6461 -0.2345 0.038 Uiso 1 1 calc R . .
C9 C 0.41515(18) -0.7308(5) -0.27565(15) 0.0206(7) Uani 1 1 d . . .
H9 H 0.4120 -0.8656 -0.2743 0.025 Uiso 1 1 calc R . .
C10 C 0.45672(18) -0.6300(5) -0.30534(15) 0.0207(7) Uani 1 1 d . . .
H10 H 0.4886 -0.6800 -0.3289 0.025 Uiso 1 1 calc R . .
C11 C 0.47634(16) -0.2828(5) -0.32107(14) 0.0180(7) Uani 1 1 d . . .
C12 C 0.5524(2) -0.2130(7) -0.38933(17) 0.0299(9) Uani 1 1 d . . .
H12A H 0.5930 -0.2683 -0.4023 0.036 Uiso 1 1 calc R . .
H12B H 0.5624 -0.1015 -0.3660 0.036 Uiso 1 1 calc R . .
C13 C 0.5139(2) -0.1501(10) -0.4379(2) 0.0505(15) Uani 1 1 d . . .
H13A H 0.5015 -0.2615 -0.4597 0.076 Uiso 1 1 calc R . .
H13B H 0.5392 -0.0639 -0.4608 0.076 Uiso 1 1 calc R . .
H13C H 0.4757 -0.0838 -0.4251 0.076 Uiso 1 1 calc R . .
N1 N 0.37750(15) -0.6022(4) -0.24708(12) 0.0178(6) Uani 1 1 d . . .
N2 N 0.44448(14) -0.4371(4) -0.29527(12) 0.0161(6) Uani 1 1 d . . .
O1 O 0.46702(14) -0.1197(4) -0.31173(11) 0.0244(6) Uani 1 1 d . . .
O2 O 0.51809(14) -0.3540(4) -0.35685(12) 0.0277(6) Uani 1 1 d . . .
S1 S 0.36004(4) -0.22392(13) -0.23212(3) 0.01821(19) Uani 1 1 d . . .
I1 I 0.199749(11) 0.08303(3) 0.153060(9) 0.01702(9) Uani 1 1 d . . .
I2 I 0.325954(12) -0.17416(3) -0.103790(9) 0.01944(9) Uani 1 1 d . . .
F1 F 0.13699(10) -0.0531(3) 0.03960(9) 0.0249(5) Uani 1 1 d . . .
F2 F 0.18525(11) -0.1559(3) -0.05672(9) 0.0218(5) Uani 1 1 d . . .
F3 F 0.39265(10) -0.0381(4) 0.01036(9) 0.0262(5) Uani 1 1 d . . .
F4 F 0.34428(11) 0.0620(3) 0.10766(8) 0.0221(5) Uani 1 1 d . . .
 
 
_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 C6 1.379(5) . ?
C1 C2 1.390(5) . ?
C1 I1 2.100(3) . ?
C2 F1 1.343(4) . ?
C2 C3 1.380(5) . ?
C3 F2 1.352(4) . ?
C3 C4 1.377(5) . ?
C4 C5 1.387(5) . ?
C4 I2 2.097(3) . ?
C5 F3 1.348(4) . ?
C5 C6 1.383(5) . ?
C6 F4 1.348(4) . ?
C7 N1 1.349(4) . ?
C7 N2 1.384(4) . ?
C7 S1 1.693(4) . ?
C8 N1 1.463(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.337(6) . ?
C9 N1 1.388(5) . ?
C9 H9 0.9500 . ?
C10 N2 1.401(5) . ?
C10 H10 0.9500 . ?
C11 O1 1.185(5) . ?
C11 O2 1.334(4) . ?
C11 N2 1.421(5) . ?
C12 O2 1.459(5) . ?
C12 C13 1.499(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
 
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
C6 C1 C2 117.3(3) . . ?
C6 C1 I1 122.4(2) . . ?
C2 C1 I1 120.3(2) . . ?
F1 C2 C3 118.4(3) . . ?
F1 C2 C1 120.7(3) . . ?
C3 C2 C1 120.9(3) . . ?
F2 C3 C4 120.2(3) . . ?
F2 C3 C2 117.9(3) . . ?
C4 C3 C2 121.9(3) . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 I2 120.2(3) . . ?
C5 C4 I2 122.7(3) . . ?
F3 C5 C6 118.7(3) . . ?
F3 C5 C4 120.1(3) . . ?
C6 C5 C4 121.2(3) . . ?
F4 C6 C1 120.2(3) . . ?
F4 C6 C5 118.3(3) . . ?
C1 C6 C5 121.5(3) . . ?
N1 C7 N2 105.1(3) . . ?
N1 C7 S1 125.5(3) . . ?
N2 C7 S1 129.5(3) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 107.4(3) . . ?
C10 C9 H9 126.3 . . ?
N1 C9 H9 126.3 . . ?
C9 C10 N2 107.3(3) . . ?
C9 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
O1 C11 O2 126.7(3) . . ?
O1 C11 N2 125.1(3) . . ?
O2 C11 N2 108.2(3) . . ?
O2 C12 C13 111.0(4) . . ?
O2 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O2 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C9 111.0(3) . . ?
C7 N1 C8 124.7(3) . . ?
C9 N1 C8 124.1(3) . . ?
C7 N2 C10 109.2(3) . . ?
C7 N2 C11 125.6(3) . . ?
C10 N2 C11 125.1(3) . . ?
C11 O2 C12 115.1(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.782
_refine_diff_density_min   -1.404
_refine_diff_density_rms    0.172
