 
data_solution
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H22 I2 N2 O2'
_chemical_formula_sum
 'C20 H22 I2 N2 O2'
_chemical_formula_weight          576.20
 
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'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pca2(1)
_symmetry_space_group_name_hall   'P 2c -2ac'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y, z+1/2'
 'x+1/2, -y, z'
 
_cell_length_a                    13.4920(5)
_cell_length_b                    4.7287(2)
_cell_length_c                    31.3743(16)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2001.67(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3639
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.912
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1112
_exptl_absorpt_coefficient_mu     3.159
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7430
_exptl_absorpt_correction_T_max   0.9112
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 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             8445
_diffrn_reflns_av_R_equivalents   0.0676
_diffrn_reflns_av_sigmaI/netI     0.0825
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        40
_diffrn_reflns_theta_min          3.29
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3058
_reflns_number_gt                 2483
_reflns_threshold_expression      >2σ(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     'PLATON (Watkin, Pearce 1995)'
_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 > 2σ(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)+(0.0176P)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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.15(5)
_refine_ls_number_reflns          3058
_refine_ls_number_parameters      236
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0580
_refine_ls_R_factor_gt            0.0394
_refine_ls_wR_factor_ref          0.0726
_refine_ls_wR_factor_gt           0.0674
_refine_ls_goodness_of_fit_ref    0.998
_refine_ls_restrained_S_all       0.998
_refine_ls_shift/su_max           0.012
_refine_ls_shift/su_mean          0.002
 
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
I2 I 0.34807(4) 1.11239(10) 0.686526(18) 0.02193(15) Uani 1 1 d . . .
I1 I -0.11842(4) 1.08988(10) 1.008260(17) 0.02244(15) Uani 1 1 d . . .
O2 O 0.0083(4) 0.9586(13) 0.85777(19) 0.0204(15) Uani 1 1 d . . .
N2 N 0.1262(4) 0.7562(14) 0.7906(2) 0.0158(15) Uani 1 1 d . . .
O1 O 0.2257(4) 0.9806(15) 0.8413(2) 0.0229(16) Uani 1 1 d . . .
C11 C 0.0758(6) 0.7308(17) 0.8651(3) 0.0183(19) Uani 1 1 d . . .
H11 H 0.0397 0.5480 0.8612 0.022 Uiso 1 1 calc R . .
C12 C -0.0297(7) 0.9570(19) 0.8155(3) 0.024(2) Uani 1 1 d . . .
H12A H -0.0776 1.1138 0.8118 0.029 Uiso 1 1 calc R . .
H12B H -0.0648 0.7767 0.8100 0.029 Uiso 1 1 calc R . .
C9 C 0.2609(6) 0.9789(19) 0.8844(3) 0.025(2) Uani 1 1 d . . .
H9A H 0.3056 1.1424 0.8889 0.030 Uiso 1 1 calc R . .
H9B H 0.2994 0.8040 0.8895 0.030 Uiso 1 1 calc R . .
N1 N 0.1103(5) 0.7474(14) 0.9086(2) 0.0185(16) Uani 1 1 d . . .
C7 C 0.0287(6) 0.7479(18) 0.9390(3) 0.021(2) Uani 1 1 d . . .
H7A H -0.0173 0.5924 0.9316 0.026 Uiso 1 1 calc R . .
H7B H -0.0081 0.9279 0.9360 0.026 Uiso 1 1 calc R . .
C14 C 0.2074(6) 0.772(2) 0.7594(2) 0.022(2) Uani 1 1 d . . .
H14A H 0.2568 0.6237 0.7662 0.026 Uiso 1 1 calc R . .
H14B H 0.2406 0.9575 0.7622 0.026 Uiso 1 1 calc R . .
C20 C 0.0941(6) 0.5486(18) 0.7048(3) 0.021(2) Uani 1 1 d . . .
H20 H 0.0605 0.4560 0.7274 0.025 Uiso 1 1 calc R . .
C5 C 0.1398(6) 0.5402(18) 0.9956(3) 0.020(2) Uani 1 1 d . . .
H5 H 0.1767 0.4528 0.9734 0.024 Uiso 1 1 calc R . .
C4 C 0.1672(8) 0.4923(18) 1.0373(3) 0.024(2) Uani 1 1 d . . .
H4 H 0.2222 0.3742 1.0435 0.029 Uiso 1 1 calc R . .
C10 C 0.1620(5) 0.7419(17) 0.8335(3) 0.0141(19) Uani 1 1 d . . .
H10 H 0.2020 0.5651 0.8367 0.017 Uiso 1 1 calc R . .
C8 C 0.1769(6) 0.9938(17) 0.9152(3) 0.018(2) Uani 1 1 d . . .
H8A H 0.2027 0.9923 0.9448 0.022 Uiso 1 1 calc R . .
H8B H 0.1395 1.1717 0.9109 0.022 Uiso 1 1 calc R . .
C13 C 0.0548(6) 0.9908(16) 0.7843(3) 0.016(2) Uani 1 1 d . . .
H13A H 0.0291 0.9872 0.7547 0.020 Uiso 1 1 calc R . .
H13B H 0.0883 1.1745 0.7890 0.020 Uiso 1 1 calc R . .
C17 C 0.1882(6) 0.8156(18) 0.6378(3) 0.018(2) Uani 1 1 d . . .
H17 H 0.2197 0.9104 0.6148 0.021 Uiso 1 1 calc R . .
C3 C 0.1140(6) 0.6173(18) 1.0701(3) 0.023(2) Uani 1 1 d . . .
H3 H 0.1309 0.5814 1.0990 0.027 Uiso 1 1 calc R . .
C19 C 0.0642(8) 0.4997(17) 0.6640(3) 0.022(2) Uani 1 1 d . . .
H19 H 0.0111 0.3721 0.6590 0.026 Uiso 1 1 calc R . .
C18 C 0.1096(6) 0.6327(16) 0.6296(3) 0.022(2) Uani 1 1 d . . .
H18 H 0.0876 0.5995 0.6013 0.026 Uiso 1 1 calc R . .
C2 C 0.0355(7) 0.7959(19) 1.0600(3) 0.023(2) Uani 1 1 d . . .
H2 H -0.0003 0.8884 1.0820 0.027 Uiso 1 1 calc R . .
C6 C 0.0589(6) 0.7148(17) 0.9848(3) 0.016(2) Uani 1 1 d . . .
C16 C 0.2210(6) 0.8610(16) 0.6795(3) 0.014(2) Uani 1 1 d . . .
C1 C 0.0096(6) 0.8387(17) 1.0180(3) 0.019(2) Uani 1 1 d . . .
C15 C 0.1748(6) 0.7352(19) 0.7147(3) 0.019(2) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
I2 C16 2.098(8) . ?
I1 C1 2.119(8) . ?
O2 C12 1.423(9) . ?
O2 C11 1.430(9) . ?
N2 C10 1.432(9) . ?
N2 C14 1.472(9) . ?
N2 C13 1.482(9) . ?
O1 C9 1.433(11) . ?
O1 C10 1.440(10) . ?
C11 N1 1.443(9) . ?
C11 C10 1.528(9) . ?
C11 H11 1.0000 . ?
C12 C13 1.512(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 C8 1.492(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 C7 1.457(10) . ?
N1 C8 1.487(10) . ?
C7 C6 1.503(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 C15 1.477(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C20 C19 1.359(11) . ?
C20 C15 1.436(12) . ?
C20 H20 0.9500 . ?
C5 C4 1.378(13) . ?
C5 C6 1.410(11) . ?
C5 H5 0.9500 . ?
C4 C3 1.387(13) . ?
C4 H4 0.9500 . ?
C10 H10 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C17 C18 1.391(11) . ?
C17 C16 1.398(11) . ?
C17 H17 0.9500 . ?
C3 C2 1.392(12) . ?
C3 H3 0.9500 . ?
C19 C18 1.391(12) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C2 C1 1.377(11) . ?
C2 H2 0.9500 . ?
C6 C1 1.367(10) . ?
C16 C15 1.402(11) . ?
 
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
C12 O2 C11 112.1(6) . . ?
C10 N2 C14 112.1(6) . . ?
C10 N2 C13 112.4(6) . . ?
C14 N2 C13 110.9(6) . . ?
C9 O1 C10 110.7(7) . . ?
O2 C11 N1 108.4(6) . . ?
O2 C11 C10 110.8(7) . . ?
N1 C11 C10 111.5(6) . . ?
O2 C11 H11 108.7 . . ?
N1 C11 H11 108.7 . . ?
C10 C11 H11 108.7 . . ?
O2 C12 C13 109.4(7) . . ?
O2 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O2 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O1 C9 C8 111.1(7) . . ?
O1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 N1 C7 112.1(6) . . ?
C11 N1 C8 111.7(6) . . ?
C7 N1 C8 111.3(6) . . ?
N1 C7 C6 115.0(7) . . ?
N1 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N2 C14 C15 113.8(7) . . ?
N2 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C19 C20 C15 122.3(9) . . ?
C19 C20 H20 118.8 . . ?
C15 C20 H20 118.8 . . ?
C4 C5 C6 122.0(8) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C4 C3 119.8(9) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N2 C10 O1 108.9(6) . . ?
N2 C10 C11 110.7(6) . . ?
O1 C10 C11 111.8(7) . . ?
N2 C10 H10 108.4 . . ?
O1 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
N1 C8 C9 109.3(7) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C13 C12 108.9(7) . . ?
N2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C18 C17 C16 120.6(8) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C4 C3 C2 118.9(8) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C20 C19 C18 121.4(9) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C18 C17 118.3(8) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C1 C2 C3 120.0(8) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C6 C5 116.5(8) . . ?
C1 C6 C7 123.5(7) . . ?
C5 C6 C7 120.0(8) . . ?
C17 C16 C15 122.2(8) . . ?
C17 C16 I2 116.4(6) . . ?
C15 C16 I2 121.3(6) . . ?
C6 C1 C2 122.8(8) . . ?
C6 C1 I1 121.8(6) . . ?
C2 C1 I1 115.3(6) . . ?
C16 C15 C20 115.2(8) . . ?
C16 C15 C14 124.5(8) . . ?
C20 C15 C14 120.3(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.913
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.913
_refine_diff_density_max    0.953
_refine_diff_density_min   -0.979
_refine_diff_density_rms    0.167
