 
data_2009src0239
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H28 I2 N4 O2'
_chemical_formula_weight          586.24
 
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    P212121
 
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'
 
_cell_length_a                    8.9301(2)
_cell_length_b                    10.8793(2)
_cell_length_c                    23.2605(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2259.83(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12375
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.43
_exptl_crystal_size_mid           0.35
_exptl_crystal_size_min           0.15
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.723
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1144
_exptl_absorpt_coefficient_mu     2.802
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.3788
_exptl_absorpt_correction_T_max   0.6786
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19225
_diffrn_reflns_av_R_equivalents   0.0479
_diffrn_reflns_av_sigmaI/netI     0.0518
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5180
_reflns_number_gt                 4674
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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.

 The large Ueq(max)/Ueq(min) ratio for the carbon and hydrogen atoms is due
 to the dimethyl groups on the imidazolium groups being able to rotate,
 thus creating larger ellipsoids than usual. It was not possible, however,
 to model these atoms as disordered.
;
 
_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)+(0.0272P)²+1.0155P] 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    -0.01(2)
_refine_ls_number_reflns          5180
_refine_ls_number_parameters      239
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0374
_refine_ls_R_factor_gt            0.0313
_refine_ls_wR_factor_ref          0.0723
_refine_ls_wR_factor_gt           0.0689
_refine_ls_goodness_of_fit_ref    1.045
_refine_ls_restrained_S_all       1.045
_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
C6 C 0.5241(5) 1.0459(4) 0.2045(2) 0.0282(11) Uani 1 1 d . . .
H6 H 0.5414 1.0371 0.1622 0.034 Uiso 1 1 calc R . .
C7 C 0.6500(5) 0.9817(5) 0.2359(2) 0.0393(14) Uani 1 1 d . . .
H7A H 0.6339 0.9883 0.2775 0.059 Uiso 1 1 calc R . .
H7B H 0.7456 1.0203 0.2258 0.059 Uiso 1 1 calc R . .
H7C H 0.6521 0.8948 0.2248 0.059 Uiso 1 1 calc R . .
C8 C 0.5163(6) 1.1830(4) 0.2189(2) 0.0339(12) Uani 1 1 d . . .
H8A H 0.4247 1.2182 0.2025 0.051 Uiso 1 1 calc R . .
H8B H 0.6038 1.2250 0.2027 0.051 Uiso 1 1 calc R . .
H8C H 0.5155 1.1937 0.2607 0.051 Uiso 1 1 calc R . .
C9 C 0.0701(4) 0.7824(3) 0.19014(16) 0.0146(8) Uani 1 1 d . . .
H9 H 0.0131 0.7457 0.2229 0.018 Uiso 1 1 calc R . .
C10 C 0.1435(4) 0.6810(3) 0.15390(17) 0.0137(8) Uani 1 1 d . . .
H10 H 0.2485 0.6640 0.1666 0.016 Uiso 1 1 calc R . .
C12 C -0.0365(4) 0.8417(4) 0.14734(18) 0.0180(9) Uani 1 1 d . . .
H12A H -0.1342 0.7986 0.1472 0.022 Uiso 1 1 calc R . .
H12B H -0.0534 0.9291 0.1571 0.022 Uiso 1 1 calc R . .
C13 C 0.0241(4) 1.0578(4) 0.39875(19) 0.0179(9) Uani 1 1 d . . .
H13A H 0.1237 1.0976 0.3976 0.022 Uiso 1 1 calc R . .
H13B H 0.0371 0.9697 0.4081 0.022 Uiso 1 1 calc R . .
C15 C -0.1376(4) 1.2290(3) 0.40799(17) 0.0129(8) Uani 1 1 d . . .
H15 H -0.2392 1.2540 0.4218 0.015 Uiso 1 1 calc R . .
C16 C -0.0769(4) 1.1203(3) 0.44262(16) 0.0137(8) Uani 1 1 d . . .
H16 H -0.0189 1.1487 0.4769 0.016 Uiso 1 1 calc R . .
C22 C -0.4695(5) 0.7977(4) 0.4342(2) 0.0267(10) Uani 1 1 d . . .
H22 H -0.4260 0.7708 0.3967 0.032 Uiso 1 1 calc R . .
C23 C -0.4674(8) 0.6901(5) 0.4740(3) 0.0602(19) Uani 1 1 d . . .
H23A H -0.3645 0.6603 0.4782 0.090 Uiso 1 1 calc R . .
H23B H -0.5303 0.6244 0.4582 0.090 Uiso 1 1 calc R . .
H23C H -0.5062 0.7149 0.5116 0.090 Uiso 1 1 calc R . .
C24 C -0.6283(6) 0.8448(6) 0.4227(3) 0.0541(18) Uani 1 1 d . . .
H24A H -0.6709 0.8775 0.4584 0.081 Uiso 1 1 calc R . .
H24B H -0.6907 0.7770 0.4088 0.081 Uiso 1 1 calc R . .
H24C H -0.6249 0.9099 0.3937 0.081 Uiso 1 1 calc R . .
O11 O 0.0362(3) 0.8307(2) 0.09167(12) 0.0200(7) Uani 1 1 d . . .
O14 O -0.0524(3) 1.0723(2) 0.34473(11) 0.0172(6) Uani 1 1 d . . .
C2 C 0.3074(5) 0.9088(4) 0.18471(17) 0.0192(9) Uani 1 1 d . . .
H2 H 0.3386 0.8848 0.1473 0.023 Uiso 1 1 calc R . .
C4 C 0.1765(5) 0.9271(4) 0.26436(18) 0.0205(10) Uani 1 1 d . . .
H4 H 0.1007 0.9169 0.2926 0.025 Uiso 1 1 calc R . .
C5 C 0.2968(5) 1.0000(4) 0.26835(18) 0.0212(9) Uani 1 1 d . . .
H5 H 0.3207 1.0518 0.2999 0.025 Uiso 1 1 calc R . .
C18 C -0.2618(4) 0.9492(4) 0.42828(17) 0.0148(8) Uani 1 1 d . . .
H18 H -0.2272 0.9243 0.3915 0.018 Uiso 1 1 calc R . .
C20 C -0.3910(5) 0.9621(4) 0.50854(19) 0.0246(10) Uani 1 1 d . . .
H20 H -0.4638 0.9467 0.5375 0.030 Uiso 1 1 calc R . .
C21 C -0.2827(5) 1.0490(4) 0.51013(17) 0.0189(9) Uani 1 1 d . . .
H21 H -0.2648 1.1057 0.5404 0.023 Uiso 1 1 calc R . .
N1 N 0.3799(4) 0.9869(3) 0.21892(15) 0.0175(8) Uani 1 1 d . . .
N3 N 0.1832(4) 0.8694(3) 0.21138(14) 0.0147(7) Uani 1 1 d . . .
N17 N -0.2035(3) 1.0397(3) 0.45959(13) 0.0136(7) Uani 1 1 d . . .
N19 N -0.3760(4) 0.8992(3) 0.45648(15) 0.0181(8) Uani 1 1 d . . .
I1 I 0.56467(3) 0.71043(2) 0.100494(11) 0.01982(8) Uani 1 1 d . . .
I2 I -0.07227(3) 0.69460(2) 0.351234(12) 0.02396(8) 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
C6 N1 1.478(5) . ?
C6 C7 1.512(7) . ?
C6 C8 1.530(7) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N3 1.470(5) . ?
C9 C12 1.521(5) . ?
C9 C10 1.535(5) . ?
C9 H9 1.0000 . ?
C10 O14 1.436(4) 3_545 ?
C10 C15 1.532(5) 3_545 ?
C10 H10 1.0000 . ?
C12 O11 1.454(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.439(5) . ?
C13 C16 1.523(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 O11 1.430(4) 3 ?
C15 C16 1.529(5) . ?
C15 C10 1.532(5) 3 ?
C15 H15 1.0000 . ?
C16 N17 1.484(5) . ?
C16 H16 1.0000 . ?
C22 N19 1.478(5) . ?
C22 C23 1.492(7) . ?
C22 C24 1.531(7) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O11 C15 1.430(4) 3_545 ?
O14 C10 1.436(4) 3 ?
C2 N1 1.333(5) . ?
C2 N3 1.341(5) . ?
C2 H2 0.9500 . ?
C4 C5 1.338(6) . ?
C4 N3 1.384(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.376(5) . ?
C5 H5 0.9500 . ?
C18 N19 1.329(5) . ?
C18 N17 1.331(5) . ?
C18 H18 0.9500 . ?
C20 C21 1.353(6) . ?
C20 N19 1.397(6) . ?
C20 H20 0.9500 . ?
C21 N17 1.376(5) . ?
C21 H21 0.9500 . ?
 
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
N1 C6 C7 109.7(4) . . ?
N1 C6 C8 109.5(4) . . ?
C7 C6 C8 112.3(4) . . ?
N1 C6 H6 108.4 . . ?
C7 C6 H6 108.4 . . ?
C8 C6 H6 108.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C12 112.1(3) . . ?
N3 C9 C10 110.7(3) . . ?
C12 C9 C10 102.3(3) . . ?
N3 C9 H9 110.5 . . ?
C12 C9 H9 110.5 . . ?
C10 C9 H9 110.5 . . ?
O14 C10 C15 106.4(3) 3_545 3_545 ?
O14 C10 C9 109.7(3) 3_545 . ?
C15 C10 C9 104.9(3) 3_545 . ?
O14 C10 H10 111.8 3_545 . ?
C15 C10 H10 111.8 3_545 . ?
C9 C10 H10 111.8 . . ?
O11 C12 C9 105.6(3) . . ?
O11 C12 H12A 110.6 . . ?
C9 C12 H12A 110.6 . . ?
O11 C12 H12B 110.6 . . ?
C9 C12 H12B 110.6 . . ?
H12A C12 H12B 108.8 . . ?
O14 C13 C16 104.8(3) . . ?
O14 C13 H13A 110.8 . . ?
C16 C13 H13A 110.8 . . ?
O14 C13 H13B 110.8 . . ?
C16 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O11 C15 C16 111.8(3) 3 . ?
O11 C15 C10 106.9(3) 3 3 ?
C16 C15 C10 104.1(3) . 3 ?
O11 C15 H15 111.3 3 . ?
C16 C15 H15 111.3 . . ?
C10 C15 H15 111.3 3 . ?
N17 C16 C13 111.4(3) . . ?
N17 C16 C15 109.1(3) . . ?
C13 C16 C15 101.7(3) . . ?
N17 C16 H16 111.4 . . ?
C13 C16 H16 111.4 . . ?
C15 C16 H16 111.4 . . ?
N19 C22 C23 111.2(4) . . ?
N19 C22 C24 109.6(4) . . ?
C23 C22 C24 112.4(5) . . ?
N19 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
C24 C22 H22 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 O11 C12 110.0(3) 3_545 . ?
C10 O14 C13 109.9(3) 3 . ?
N1 C2 N3 109.3(4) . . ?
N1 C2 H2 125.4 . . ?
N3 C2 H2 125.4 . . ?
C5 C4 N3 107.2(4) . . ?
C5 C4 H4 126.4 . . ?
N3 C4 H4 126.4 . . ?
C4 C5 N1 108.3(4) . . ?
C4 C5 H5 125.9 . . ?
N1 C5 H5 125.9 . . ?
N19 C18 N17 109.5(3) . . ?
N19 C18 H18 125.3 . . ?
N17 C18 H18 125.3 . . ?
C21 C20 N19 107.3(4) . . ?
C21 C20 H20 126.3 . . ?
N19 C20 H20 126.3 . . ?
C20 C21 N17 107.1(4) . . ?
C20 C21 H21 126.5 . . ?
N17 C21 H21 126.5 . . ?
C2 N1 C5 107.6(3) . . ?
C2 N1 C6 124.4(4) . . ?
C5 N1 C6 128.0(4) . . ?
C2 N3 C4 107.6(3) . . ?
C2 N3 C9 128.2(3) . . ?
C4 N3 C9 124.2(3) . . ?
C18 N17 C21 108.7(3) . . ?
C18 N17 C16 126.2(3) . . ?
C21 N17 C16 125.2(3) . . ?
C18 N19 C20 107.5(3) . . ?
C18 N19 C22 124.5(4) . . ?
C20 N19 C22 128.0(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.061
_refine_diff_density_min   -0.846
_refine_diff_density_rms    0.132
