# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_ha1183

_audit_creation_method           'manual editing of SHELXL-97 cif file'

_chemical_name_systematic        
; 
1-Iodo-3,5-bis(4',4',5',5'-tetramethyl-4',5'-dihydro-
1'H-imidazole-1'-oxyl)benzene - co - dichloromethane
;
_chemical_name_common            ?
_chemical_melting_point          183
_chemical_formula_moiety         'C20 H27 I N4 O2, C H2 Cl2, H0.72 O0.36'
_chemical_formula_sum            'C21 H29.72 Cl2 I N4 O2.36'
_chemical_formula_weight         573.77

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'
Cl Cl 0.1484 0.1585 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_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                   13.7450(8)
_cell_length_b                   24.8293(14)
_cell_length_c                   7.2076(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.1910(10)
_cell_angle_gamma                90.00
_cell_volume                     2449.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    95(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      2.513
_cell_measurement_theta_max      17.287

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1158
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'

_exptl_special_details           
;
The data collection nominally covered over a hemisphere of reciprocal
space by a combination of two sets of exposures; each set had a
different ω angle for the crystal and each exposure covered 0.5° in φ.
;

_diffrn_ambient_temperature      95(2)
_diffrn_radiation_wavelength     0.39360
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_source_type              'APS 15-ID'
_diffrn_radiation_monochromator  'diamond 1 1 1'
_diffrn_measurement_device_type  'three circle goniometer with fixed chi'
_diffrn_measurement_method       'phi scans'
_diffrn_detector_area_resol_mean 83.33
_diffrn_reflns_number            28097
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         17.32
_diffrn_measured_fraction_theta_max 0.936
_diffrn_reflns_theta_full        17.32
_diffrn_measured_fraction_theta_full 0.936

_reflns_number_total             4169
_reflns_number_gt                3801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II v.2.2 (Bruker, 2007)'
_computing_cell_refinement       'APEX II v.2.2 (Bruker, 2007)'
_computing_data_reduction        'APEX II v.2.2 (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 3.1a (Crystal Impact, 2005)'
_computing_publication_material  'SHELXTL (Bruker, 2006)'

_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)+(0.0562P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4169
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.873
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.131

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 0.5000 -0.138371(9) 0.2500 0.01960(11) Uani 1 2 d S . .
O1 O 0.23129(14) -0.00422(8) -0.0369(3) 0.0180(4) Uani 1 1 d . . .
N1 N 0.24424(14) 0.04237(8) 0.0339(3) 0.0125(4) Uani 1 1 d . . .
N2 N 0.32012(15) 0.11158(8) 0.1842(3) 0.0152(4) Uani 1 1 d . . .
C1 C 0.5000 -0.05412(12) 0.2500 0.0112(5) Uani 1 2 d S . .
C2 C 0.41535(16) -0.02719(9) 0.1839(3) 0.0117(4) Uani 1 1 d . . .
H2A H 0.3588 -0.0466 0.1372 0.014 Uiso 1 1 calc R . .
C3 C 0.41522(15) 0.02903(9) 0.1878(3) 0.0102(4) Uani 1 1 d . . .
C4 C 0.5000 0.05674(12) 0.2500 0.0108(5) Uani 1 2 d S . .
H4A H 0.5000 0.0950 0.2500 0.013 Uiso 1 2 calc SR . .
C7 C 0.32762(16) 0.06164(9) 0.1364(3) 0.0111(4) Uani 1 1 d . . .
C8 C 0.17414(16) 0.08739(10) -0.0088(3) 0.0131(4) Uani 1 1 d . . .
C9 C 0.21904(17) 0.13045(9) 0.1308(3) 0.0134(4) Uani 1 1 d . . .
C10 C 0.1809(2) 0.10209(12) -0.2134(4) 0.0206(5) Uani 1 1 d . . .
H10A H 0.2479 0.1130 -0.2314 0.031 Uiso 1 1 calc R . .
H10B H 0.1362 0.1319 -0.2479 0.031 Uiso 1 1 calc R . .
H10C H 0.1630 0.0708 -0.2920 0.031 Uiso 1 1 calc R . .
C11 C 0.07133(19) 0.06855(13) 0.0172(5) 0.0236(5) Uani 1 1 d . . .
H11A H 0.0706 0.0509 0.1387 0.035 Uiso 1 1 calc R . .
H11B H 0.0498 0.0429 -0.0816 0.035 Uiso 1 1 calc R . .
H11C H 0.0271 0.0996 0.0112 0.035 Uiso 1 1 calc R . .
C12 C 0.2238(2) 0.18720(11) 0.0517(4) 0.0222(5) Uani 1 1 d . . .
H12A H 0.2650 0.1872 -0.0525 0.033 Uiso 1 1 calc R . .
H12B H 0.2517 0.2117 0.1490 0.033 Uiso 1 1 calc R . .
H12C H 0.1578 0.1992 0.0076 0.033 Uiso 1 1 calc R . .
C13 C 0.1697(2) 0.13229(12) 0.3134(4) 0.0222(5) Uani 1 1 d . . .
H13A H 0.1644 0.0957 0.3623 0.033 Uiso 1 1 calc R . .
H13B H 0.1043 0.1479 0.2899 0.033 Uiso 1 1 calc R . .
H13C H 0.2088 0.1544 0.4046 0.033 Uiso 1 1 calc R . .
Cl1 Cl 0.05560(7) 0.24190(4) 0.58763(14) 0.0372(2) Uani 1 1 d . . .
C23 C 0.0000 0.28223(18) 0.7500 0.0290(9) Uani 1 2 d S . .
H23 H -0.045(3) 0.3039(19) 0.681(7) 0.035 Uiso 1 1 d . . .
O2 O 0.2677(6) 0.2244(3) 0.4196(13) 0.009(2) Uiso 0.180(9) 1 d P . .

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 0.02107(15) 0.00995(13) 0.02825(18) 0.000 0.00479(9) 0.000
O1 0.0196(8) 0.0158(8) 0.0174(10) -0.0030(6) -0.0043(6) -0.0017(6)
N1 0.0127(8) 0.0134(8) 0.0105(10) 0.0015(6) -0.0032(6) 0.0004(6)
N2 0.0148(8) 0.0139(8) 0.0161(10) -0.0010(7) -0.0024(7) 0.0015(7)
C1 0.0146(13) 0.0089(11) 0.0104(14) 0.000 0.0027(10) 0.000
C2 0.0122(9) 0.0123(9) 0.0105(10) 0.0003(7) 0.0012(7) -0.0013(7)
C3 0.0101(8) 0.0122(8) 0.0081(10) 0.0006(6) -0.0005(7) 0.0002(6)
C4 0.0133(12) 0.0097(11) 0.0091(14) 0.000 -0.0014(10) 0.000
C7 0.0113(8) 0.0140(9) 0.0079(10) 0.0014(7) 0.0002(7) -0.0005(7)
C8 0.0106(8) 0.0166(9) 0.0117(11) 0.0016(7) -0.0006(7) 0.0020(7)
C9 0.0146(9) 0.0135(9) 0.0119(11) 0.0001(7) 0.0001(7) 0.0017(7)
C10 0.0242(12) 0.0250(12) 0.0121(12) 0.0039(9) -0.0008(9) 0.0075(9)
C11 0.0149(10) 0.0310(14) 0.0253(15) -0.0051(11) 0.0039(9) -0.0024(9)
C12 0.0261(12) 0.0151(10) 0.0243(15) 0.0070(9) -0.0035(10) 0.0007(9)
C13 0.0264(12) 0.0254(12) 0.0154(13) -0.0036(9) 0.0061(9) 0.0045(10)
Cl1 0.0454(5) 0.0289(4) 0.0371(5) 0.0020(3) 0.0017(4) 0.0070(3)
C23 0.0252(18) 0.0200(17) 0.041(3) 0.000 0.0002(17) 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 2.092(3) . ?
O1 N1 1.270(3) . ?
N1 C7 1.391(3) . ?
N1 C8 1.490(3) . ?
N2 C7 1.294(3) . ?
N2 C9 1.484(3) . ?
C1 C2 1.388(3) . ?
C1 C2 1.388(3) 2_655 ?
C2 C3 1.396(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C7 1.470(3) . ?
C4 C3 1.392(3) 2_655 ?
C4 H4A 0.9500 . ?
C8 C11 1.516(3) . ?
C8 C10 1.530(4) . ?
C8 C9 1.557(3) . ?
C9 C12 1.524(3) . ?
C9 C13 1.535(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
Cl1 C23 1.766(3) . ?
C23 Cl1 1.766(3) 2_556 ?
C23 H23 0.93(5) . ?
O2 O2 1.814(18) 7_556 ?

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
O1 N1 C7 127.3(2) . . ?
O1 N1 C8 122.4(2) . . ?
C7 N1 C8 109.76(18) . . ?
C7 N2 C9 109.2(2) . . ?
C2 C1 C2 122.4(3) . 2_655 ?
C2 C1 I1 118.79(14) . . ?
C2 C1 I1 118.79(14) 2_655 . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 C7 116.8(2) . . ?
C2 C3 C7 123.2(2) . . ?
C3 C4 C3 120.8(3) . 2_655 ?
C3 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 2_655 . ?
N2 C7 N1 112.9(2) . . ?
N2 C7 C3 123.0(2) . . ?
N1 C7 C3 124.1(2) . . ?
N1 C8 C11 109.6(2) . . ?
N1 C8 C10 106.47(19) . . ?
C11 C8 C10 109.4(2) . . ?
N1 C8 C9 99.82(17) . . ?
C11 C8 C9 116.8(2) . . ?
C10 C8 C9 113.8(2) . . ?
N2 C9 C12 108.6(2) . . ?
N2 C9 C13 105.3(2) . . ?
C12 C9 C13 109.3(2) . . ?
N2 C9 C8 104.95(18) . . ?
C12 C9 C8 114.9(2) . . ?
C13 C9 C8 113.2(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Cl1 C23 Cl1 110.9(2) . 2_556 ?
Cl1 C23 H23 106(3) . . ?
Cl1 C23 H23 112(3) 2_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 -1.27(15) 2_655 . . . ?
I1 C1 C2 C3 178.73(15) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C1 C2 C3 C7 -174.68(19) . . . . ?
C2 C3 C4 C3 -1.29(15) . . . 2_655 ?
C7 C3 C4 C3 176.1(2) . . . 2_655 ?
C9 N2 C7 N1 6.3(3) . . . . ?
C9 N2 C7 C3 -173.1(2) . . . . ?
O1 N1 C7 N2 177.5(2) . . . . ?
C8 N1 C7 N2 6.3(3) . . . . ?
O1 N1 C7 C3 -3.0(4) . . . . ?
C8 N1 C7 C3 -174.3(2) . . . . ?
C4 C3 C7 N2 -15.7(3) . . . . ?
C2 C3 C7 N2 161.6(2) . . . . ?
C4 C3 C7 N1 164.9(2) . . . . ?
C2 C3 C7 N1 -17.8(4) . . . . ?
O1 N1 C8 C11 50.2(3) . . . . ?
C7 N1 C8 C11 -138.0(2) . . . . ?
O1 N1 C8 C10 -68.0(3) . . . . ?
C7 N1 C8 C10 103.8(2) . . . . ?
O1 N1 C8 C9 173.4(2) . . . . ?
C7 N1 C8 C9 -14.8(2) . . . . ?
C7 N2 C9 C12 -139.0(2) . . . . ?
C7 N2 C9 C13 104.1(2) . . . . ?
C7 N2 C9 C8 -15.6(3) . . . . ?
N1 C8 C9 N2 17.6(2) . . . . ?
C11 C8 C9 N2 135.5(2) . . . . ?
C10 C8 C9 N2 -95.5(2) . . . . ?
N1 C8 C9 C12 136.7(2) . . . . ?
C11 C8 C9 C12 -105.3(3) . . . . ?
C10 C8 C9 C12 23.7(3) . . . . ?
N1 C8 C9 C13 -96.7(2) . . . . ?
C11 C8 C9 C13 21.3(3) . . . . ?
C10 C8 C9 C13 150.3(2) . . . . ?

#END
_database_code_depnum_ccdc_archive 'CCDC 982752'
