# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2011


data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)
_journal_coden_cambridge         1326
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       jplang@suda.edu.cn
_publ_contact_author_name        'Lang, Jian-Ping'
loop_
_publ_author_name
'Yang Chen'
'Zhou Yang'
'Xin-Yi Wu'
'Chun-Yan Ni'
'Zhi-Gang Ren'
'Hong-Xi Li'
'Jian-Ping Lang'

data_t
_database_code_depnum_ccdc_archive 'CCDC 795731'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N2, Cu I3'
_chemical_formula_sum            'C16 H22 Cu I3 N2'
_chemical_formula_weight         686.61

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'
Cu Cu 0.3201 1.2651 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.469(3)
_cell_length_b                   11.529(2)
_cell_length_c                   14.906(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.38(3)
_cell_angle_gamma                90.00
_cell_volume                     2142.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7178
_cell_measurement_theta_min      3.1533
_cell_measurement_theta_max      25.3491

_exptl_crystal_description       Block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    5.342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3605
_exptl_absorpt_correction_T_max  0.4147
_exptl_absorpt_process_details   
'Jacobson, R. (1998) Private communication to Rigaku Company, Tokyo, Japan.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku MercuryCCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10131
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3894
_reflns_number_gt                2877
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_cell_refinement       'CrystalClear, Ver. 1.30 (Rigaku/MSC, 2001)'
_computing_data_reduction        
'CrystalStructure, Ver. 3.60 (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0771P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3894
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_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
Cu1 Cu 1.26947(9) -0.03691(9) 0.25673(7) 0.0460(3) Uani 1 1 d . . .
I1 I 1.32489(6) 0.02225(7) 0.10142(5) 0.0645(3) Uani 1 1 d . . .
I2 I 1.38699(6) -0.14582(5) 0.36597(4) 0.0544(2) Uani 1 1 d . . .
I3 I 1.07774(6) 0.02357(8) 0.28950(5) 0.0769(3) Uani 1 1 d . . .
N1 N 0.8856(6) 0.2128(8) 0.4505(6) 0.060(2) Uani 1 1 d . . .
N2 N 0.6187(6) -0.1641(6) 0.1544(4) 0.0388(16) Uani 1 1 d . A .
C1 C 0.8548(9) 0.1098(12) 0.4796(7) 0.070(3) Uani 1 1 d . A .
H1 H 0.8696 0.0883 0.5394 0.084 Uiso 1 1 calc R . .
C2 C 0.8022(8) 0.0351(10) 0.4240(6) 0.058(3) Uani 1 1 d . . .
H2 H 0.7817 -0.0380 0.4457 0.069 Uiso 1 1 calc R A .
C3 C 0.7783(7) 0.0646(7) 0.3359(5) 0.0379(19) Uani 1 1 d . A .
C4 C 0.8076(7) 0.1732(7) 0.3099(6) 0.047(2) Uani 1 1 d . . .
H4 H 0.7895 0.1987 0.2516 0.056 Uiso 1 1 calc R A .
C5 C 0.8628(8) 0.2457(9) 0.3669(8) 0.060(3) Uani 1 1 d . A .
H5 H 0.8848 0.3191 0.3469 0.072 Uiso 1 1 calc R . .
C6 C 0.6761(9) -0.2054(8) 0.2225(7) 0.060(3) Uani 1 1 d . . .
H6 H 0.6798 -0.2863 0.2300 0.073 Uiso 1 1 calc R . .
C7 C 0.7305(9) -0.1362(8) 0.2831(7) 0.059(3) Uani 1 1 d . A .
H7 H 0.7728 -0.1690 0.3296 0.070 Uiso 1 1 calc R . .
C8 C 0.7218(7) -0.0160(7) 0.2740(5) 0.0365(19) Uani 1 1 d . . .
C9 C 0.6580(7) 0.0257(6) 0.2038(5) 0.0369(19) Uani 1 1 d . A .
H9 H 0.6481 0.1061 0.1971 0.044 Uiso 1 1 calc R . .
C10 C 0.6090(7) -0.0491(7) 0.1440(5) 0.038(2) Uani 1 1 d . . .
H10 H 0.5683 -0.0194 0.0953 0.046 Uiso 1 1 calc R A .
C11 C 1.0576(19) 0.258(2) 0.5239(19) 0.073(8) Uiso 0.51(3) 1 d P A 1
H11A H 1.1025 0.3155 0.5541 0.109 Uiso 0.51(3) 1 calc PR A 1
H11B H 1.0927 0.2311 0.4705 0.109 Uiso 0.51(3) 1 calc PR A 1
H11C H 1.0460 0.1932 0.5639 0.109 Uiso 0.51(3) 1 calc PR A 1
C12 C 0.9480(17) 0.314(2) 0.4971(17) 0.055(6) Uiso 0.51(3) 1 d P A 1
H12A H 0.9648 0.3675 0.4476 0.066 Uiso 0.51(3) 1 calc PR A 1
C13 C 0.889(2) 0.378(3) 0.554(2) 0.074(8) Uiso 0.51(3) 1 d P A 1
H13A H 0.9344 0.4379 0.5812 0.110 Uiso 0.51(3) 1 calc PR A 1
H13B H 0.8613 0.3288 0.6007 0.110 Uiso 0.51(3) 1 calc PR A 1
H13C H 0.8302 0.4145 0.5212 0.110 Uiso 0.51(3) 1 calc PR A 1
C11' C 1.0601(18) 0.298(3) 0.483(2) 0.078(9) Uiso 0.49(3) 1 d PD A 2
H11D H 1.1087 0.3334 0.5273 0.116 Uiso 0.49(3) 1 calc PR A 2
H11E H 1.0475 0.3523 0.4341 0.116 Uiso 0.49(3) 1 calc PR A 2
H11F H 1.0917 0.2278 0.4604 0.116 Uiso 0.49(3) 1 calc PR A 2
C12' C 0.9539(16) 0.270(2) 0.5271(17) 0.054(7) Uiso 0.49(3) 1 d PD A 2
H12B H 0.9730 0.2032 0.5659 0.065 Uiso 0.49(3) 1 calc PR A 2
C13' C 0.890(2) 0.338(3) 0.5833(18) 0.064(7) Uiso 0.49(3) 1 d P A 2
H13D H 0.8293 0.2924 0.6029 0.096 Uiso 0.49(3) 1 calc PR A 2
H13E H 0.8635 0.4054 0.5504 0.096 Uiso 0.49(3) 1 calc PR A 2
H13F H 0.9320 0.3633 0.6352 0.096 Uiso 0.49(3) 1 calc PR A 2
C14 C 0.4800(9) -0.3129(9) 0.1340(7) 0.061(3) Uani 1 1 d . A .
H14A H 0.5143 -0.3638 0.1778 0.091 Uiso 1 1 calc R . .
H14B H 0.4405 -0.3590 0.0899 0.091 Uiso 1 1 calc R . .
H14C H 0.4310 -0.2613 0.1640 0.091 Uiso 1 1 calc R . .
C15 C 0.5632(7) -0.2432(7) 0.0883(6) 0.042(2) Uani 1 1 d . . .
H15 H 0.5260 -0.1940 0.0428 0.050 Uiso 1 1 calc R A .
C16 C 0.6445(8) -0.3142(8) 0.0410(6) 0.049(2) Uani 1 1 d . A .
H16A H 0.6807 -0.3652 0.0837 0.073 Uiso 1 1 calc R . .
H16B H 0.6965 -0.2633 0.0140 0.073 Uiso 1 1 calc R . .
H16C H 0.6090 -0.3603 -0.0053 0.073 Uiso 1 1 calc R . .

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
Cu1 0.0510(7) 0.0401(6) 0.0467(6) -0.0038(5) -0.0023(5) 0.0012(5)
I1 0.0589(5) 0.0784(5) 0.0568(4) 0.0217(4) 0.0139(3) 0.0122(4)
I2 0.0720(5) 0.0397(4) 0.0506(4) -0.0078(3) -0.0182(3) 0.0075(3)
I3 0.0557(5) 0.1162(7) 0.0591(5) 0.0018(4) 0.0098(4) 0.0308(4)
N1 0.035(5) 0.080(6) 0.065(6) -0.037(5) 0.000(4) 0.000(4)
N2 0.036(4) 0.039(4) 0.041(4) 0.005(3) -0.001(3) -0.001(3)
C1 0.047(7) 0.116(10) 0.045(6) -0.002(6) -0.002(5) -0.014(7)
C2 0.060(7) 0.082(7) 0.031(5) 0.004(5) 0.003(4) -0.021(6)
C3 0.033(5) 0.046(5) 0.035(4) -0.008(4) 0.002(3) 0.000(4)
C4 0.057(6) 0.034(4) 0.048(5) 0.004(4) -0.014(5) 0.003(4)
C5 0.050(6) 0.043(5) 0.086(8) -0.018(6) -0.004(6) 0.002(5)
C6 0.080(8) 0.032(5) 0.068(6) 0.006(5) -0.014(6) -0.002(5)
C7 0.069(7) 0.049(5) 0.057(6) 0.019(5) -0.023(5) -0.005(5)
C8 0.040(5) 0.039(4) 0.031(4) 0.002(4) 0.001(4) -0.005(4)
C9 0.041(5) 0.028(4) 0.042(5) -0.002(4) -0.001(4) 0.006(4)
C10 0.038(5) 0.039(4) 0.037(4) 0.002(4) -0.006(4) 0.005(4)
C14 0.071(8) 0.056(6) 0.056(6) -0.009(5) 0.015(5) -0.009(5)
C15 0.041(5) 0.037(4) 0.046(5) -0.010(4) 0.002(4) -0.004(4)
C16 0.058(6) 0.044(5) 0.044(5) -0.002(4) 0.006(4) -0.007(5)

_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
Cu1 I2 2.5020(14) . ?
Cu1 I1 2.5258(14) . ?
Cu1 I3 2.5489(14) . ?
N1 C1 1.325(15) . ?
N1 C5 1.326(13) . ?
N1 C12 1.55(2) . ?
N1 C12' 1.56(2) . ?
N2 C6 1.317(11) . ?
N2 C10 1.340(10) . ?
N2 C15 1.500(10) . ?
C1 C2 1.353(14) . ?
C1 H1 0.9400 . ?
C2 C3 1.383(12) . ?
C2 H2 0.9400 . ?
C3 C4 1.363(12) . ?
C3 C8 1.477(11) . ?
C4 C5 1.366(12) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.372(13) . ?
C6 H6 0.9400 . ?
C7 C8 1.397(12) . ?
C7 H7 0.9400 . ?
C8 C9 1.385(11) . ?
C9 C10 1.374(11) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.55(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.36(3) . ?
C12 H12A 0.9900 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C11' C12' 1.526(19) . ?
C11' H11D 0.9700 . ?
C11' H11E 0.9700 . ?
C11' H11F 0.9700 . ?
C12' C13' 1.41(3) . ?
C12' H12B 0.9900 . ?
C13' H13D 0.9700 . ?
C13' H13E 0.9700 . ?
C13' H13F 0.9700 . ?
C14 C15 1.490(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.493(12) . ?
C15 H15 0.9900 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
I2 Cu1 I1 124.28(6) . . ?
I2 Cu1 I3 123.36(5) . . ?
I1 Cu1 I3 112.36(5) . . ?
C1 N1 C5 120.4(9) . . ?
C1 N1 C12 132.2(14) . . ?
C5 N1 C12 107.4(14) . . ?
C1 N1 C12' 107.4(14) . . ?
C5 N1 C12' 132.0(14) . . ?
C12 N1 C12' 25.1(9) . . ?
C6 N2 C10 119.6(7) . . ?
C6 N2 C15 121.3(7) . . ?
C10 N2 C15 119.1(7) . . ?
N1 C1 C2 120.7(10) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 121.0(10) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 116.3(8) . . ?
C4 C3 C8 121.9(7) . . ?
C2 C3 C8 121.8(8) . . ?
C3 C4 C5 121.3(9) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 120.2(10) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N2 C6 C7 123.2(8) . . ?
N2 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C6 C7 C8 118.4(8) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 117.4(8) . . ?
C9 C8 C3 120.6(7) . . ?
C7 C8 C3 121.9(8) . . ?
C10 C9 C8 120.7(7) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C10 C9 120.5(7) . . ?
N2 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C11 123(2) . . ?
C13 C12 N1 114.8(19) . . ?
C11 C12 N1 103.6(18) . . ?
C13 C12 H12A 104.4 . . ?
C11 C12 H12A 104.4 . . ?
N1 C12 H12A 104.4 . . ?
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 . . ?
C12' C11' H11D 109.5 . . ?
C12' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C12' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C13' C12' C11' 130(2) . . ?
C13' C12' N1 111.3(17) . . ?
C11' C12' N1 104.0(18) . . ?
C13' C12' H12B 102.6 . . ?
C11' C12' H12B 102.6 . . ?
N1 C12' H12B 102.6 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C14 C15 C16 114.1(8) . . ?
C14 C15 N2 110.1(7) . . ?
C16 C15 N2 109.6(7) . . ?
C14 C15 H15 107.6 . . ?
C16 C15 H15 107.6 . . ?
N2 C15 H15 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.220
_refine_diff_density_min         -1.809
_refine_diff_density_rms         0.175