# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_General
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_date             2010-3-20
_audit_creation_method           'by CrystalStructure 3.6.0'
_audit_update_record             ?

#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_coeditor_code           ?

#==============================================================================

# SUBMISSION DETAILS

_publ_contact_author_name        'Jian-Ping Lang'
_publ_contact_author_address     
;
College of Chemistry, Chemical Engineering and Materials Science
Soochow University
Suzhou 215123, Jiangsu
P.R.China
;
_publ_contact_author_email       jplang@suda.edu.cn
_publ_contact_author_fax         86-512-65880089
_publ_contact_author_phone       86-512-65882865
_publ_contact_letter             
;
ENTER TEXT OF LETTER
;
_publ_requested_category         FM
_publ_requested_coeditor_name    ?

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
ENTER SECTION TITLE
;
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Henry Chan'
;
FIRST AUTHORS FOOTNOTES
;
;
FIRST AUTHORS ADDRESS
;
'Yang Chen' '' ''
'Ming Dai' '' ''
'Hui-Fang Wang' '' ''
'Zhi-Gang Ren' '' ''
'Zheng-Jun Huang' '' ''
'Chun-Yan Ni' '' ''
'Jian-Ping Lang' '' ''
_publ_section_synopsis           
;
ENTER SYNOPSIS
;

#==============================================================================

# TEXT

_publ_section_abstract           
;
ENTER ABSTRACT
;
_publ_section_comment            
;
ENTER TEXT
;
_publ_section_references         
;
ENTER OTHER REFERENCES

Rigaku/MSC and Rigaku Corporation. (2004).
CrystalStructure 3.6.0.
Single Crystal Structure Analysis Software.
Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209.
Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan.

Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996)
CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK.

;
_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep         
;
ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement   
;
ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==========================================================================
data_1
_database_code_depnum_ccdc_archive 'CCDC 830727'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Cu4 I6, 2(C7 H7 N2)'
_chemical_formula_sum            'C14 H14 Cu4 I6 N4'
_chemical_formula_weight         1253.89

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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'

_cell_length_a                   10.507(2)
_cell_length_b                   10.643(2)
_cell_length_c                   23.510(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2629.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    10568
_cell_measurement_theta_min      3.2280
_cell_measurement_theta_max      27.6217

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    10.247
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.107
_exptl_absorpt_correction_T_max  0.115
_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            13142
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5733
_reflns_number_gt                4762
_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^)+(0.0633P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.16(10)
_refine_ls_number_reflns         5733
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.4099(3) 0.8031(3) 0.57702(10) 0.0520(6) Uani 1 1 d . . .
Cu2 Cu 0.5957(2) 0.8172(3) 0.67927(10) 0.0518(6) Uani 1 1 d . . .
Cu3 Cu 0.4407(2) 0.5959(3) 0.66944(10) 0.0508(6) Uani 1 1 d . . .
Cu4 Cu 0.6328(3) 0.6515(2) 0.57611(10) 0.0501(6) Uani 1 1 d . . .
I1 I 0.64993(12) 0.89822(12) 0.57430(5) 0.0405(3) Uani 1 1 d . . .
I2 I 0.34394(11) 0.82916(12) 0.68649(5) 0.0412(3) Uani 1 1 d . . .
I3 I 0.39641(12) 0.55709(13) 0.55817(5) 0.0420(3) Uani 1 1 d . . .
I4 I 0.69190(11) 0.57961(12) 0.68282(5) 0.0413(3) Uani 1 1 d . . .
I5 I 0.27822(12) 0.94162(13) 0.50486(5) 0.0452(3) Uani 1 1 d . . .
I6 I 0.69401(12) 0.95046(13) 0.76294(5) 0.0444(3) Uani 1 1 d . . .
N2 N 0.484(3) 0.368(3) 0.3143(9) 0.098(9) Uani 1 1 d . . .
N4 N 0.921(3) 1.250(3) 0.5672(10) 0.093(8) Uani 1 1 d . . .
N1 N 0.5273(13) 0.8477(13) 0.3774(6) 0.082(8) Uani 1 1 d G . .
C1 C 0.5153(13) 0.8176(15) 0.3201(5) 0.061(7) Uani 1 1 d G . .
H1 H 0.5178 0.8815 0.2925 0.073 Uiso 1 1 calc R . .
C2 C 0.4997(14) 0.6931(16) 0.3036(4) 0.075(8) Uani 1 1 d G . .
H2 H 0.4916 0.6728 0.2649 0.090 Uiso 1 1 calc R . .
C3 C 0.4960(14) 0.5987(13) 0.3445(6) 0.060(6) Uani 1 1 d G . .
C4 C 0.5080(14) 0.6288(14) 0.4017(5) 0.075(8) Uani 1 1 d G . .
H4 H 0.5055 0.5650 0.4294 0.090 Uiso 1 1 calc R . .
C5 C 0.5236(14) 0.7533(16) 0.4182(4) 0.063(7) Uani 1 1 d G . .
H5 H 0.5317 0.7737 0.4569 0.075 Uiso 1 1 calc R . .
C6 C 0.489(3) 0.469(3) 0.3278(11) 0.069(8) Uani 1 1 d . . .
C7 C 0.547(3) 0.980(3) 0.3914(11) 0.088(10) Uani 1 1 d . . .
H7A H 0.5345 1.0306 0.3576 0.132 Uiso 1 1 calc R . .
H7B H 0.6322 0.9917 0.4058 0.132 Uiso 1 1 calc R . .
H7C H 0.4856 1.0050 0.4203 0.132 Uiso 1 1 calc R . .
N3 N 0.4252(12) 1.1976(13) 0.6248(5) 0.073(7) Uani 1 1 d G . .
C8 C 0.5179(15) 1.1933(13) 0.6670(4) 0.065(7) Uani 1 1 d G . .
H8 H 0.4948 1.1759 0.7048 0.078 Uiso 1 1 calc R . .
C9 C 0.6447(14) 1.2147(14) 0.6532(5) 0.063(6) Uani 1 1 d G . .
H9 H 0.7074 1.2118 0.6817 0.075 Uiso 1 1 calc R . .
C10 C 0.6788(12) 1.2404(14) 0.5973(6) 0.064(6) Uani 1 1 d G . .
C11 C 0.5861(15) 1.2447(13) 0.5551(4) 0.056(6) Uani 1 1 d G . .
H11 H 0.6092 1.2621 0.5173 0.067 Uiso 1 1 calc R . .
C12 C 0.4593(14) 1.2233(13) 0.5689(5) 0.073(8) Uani 1 1 d G . .
H12 H 0.3967 1.2262 0.5404 0.088 Uiso 1 1 calc R . .
C13 C 0.820(3) 1.250(3) 0.5806(12) 0.083(9) Uani 1 1 d . . .
C14 C 0.299(2) 1.175(3) 0.6383(9) 0.069(7) Uani 1 1 d . . .
H14A H 0.2948 1.1211 0.6715 0.104 Uiso 1 1 calc R . .
H14B H 0.2574 1.1348 0.6065 0.104 Uiso 1 1 calc R . .
H14C H 0.2572 1.2544 0.6466 0.104 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 0.0584(15) 0.0549(16) 0.0426(13) -0.0012(12) -0.0009(12) 0.0009(13)
Cu2 0.0519(14) 0.0602(17) 0.0431(13) -0.0027(12) 0.0015(12) -0.0005(13)
Cu3 0.0506(14) 0.0595(17) 0.0423(13) 0.0006(11) -0.0016(11) -0.0034(13)
Cu4 0.0586(15) 0.0480(14) 0.0437(13) -0.0025(11) 0.0030(11) 0.0031(12)
I1 0.0471(7) 0.0399(6) 0.0343(5) -0.0006(5) 0.0043(5) -0.0021(5)
I2 0.0433(6) 0.0473(7) 0.0331(5) -0.0015(5) 0.0017(5) 0.0036(6)
I3 0.0490(6) 0.0459(7) 0.0312(5) -0.0018(5) -0.0017(5) -0.0039(6)
I4 0.0426(6) 0.0472(7) 0.0340(5) 0.0028(5) 0.0005(5) 0.0029(5)
I5 0.0524(7) 0.0455(7) 0.0378(6) -0.0019(6) -0.0079(5) -0.0020(6)
I6 0.0470(7) 0.0478(7) 0.0383(6) -0.0057(6) 0.0000(5) 0.0016(6)
N2 0.14(2) 0.11(2) 0.047(12) -0.006(14) 0.003(14) 0.02(2)
N4 0.13(2) 0.09(2) 0.060(14) 0.011(13) -0.005(16) -0.007(19)
N1 0.038(10) 0.15(3) 0.054(12) 0.010(14) 0.009(9) 0.008(13)
C1 0.029(9) 0.12(2) 0.035(10) -0.001(12) -0.007(9) 0.006(12)
C2 0.070(16) 0.13(3) 0.029(11) -0.003(14) 0.001(10) 0.002(17)
C3 0.045(11) 0.084(19) 0.052(12) -0.002(13) -0.007(10) 0.003(12)
C4 0.057(14) 0.12(2) 0.046(12) -0.003(14) 0.013(11) 0.036(16)
C5 0.066(14) 0.085(19) 0.037(11) 0.000(12) 0.001(10) 0.022(14)
C6 0.079(17) 0.073(19) 0.055(14) 0.034(13) -0.028(13) -0.008(15)
C7 0.067(17) 0.12(3) 0.076(17) -0.040(18) 0.004(14) -0.020(18)
N3 0.14(2) 0.043(11) 0.034(9) -0.012(8) 0.004(11) 0.012(12)
C8 0.12(2) 0.056(14) 0.024(9) -0.006(9) -0.008(11) 0.021(14)
C9 0.077(16) 0.058(14) 0.053(12) 0.011(11) -0.005(12) 0.024(13)
C10 0.090(18) 0.041(12) 0.059(14) 0.015(10) -0.001(13) -0.014(13)
C11 0.063(14) 0.035(11) 0.070(15) 0.011(10) 0.005(12) -0.009(10)
C12 0.13(2) 0.055(14) 0.039(12) -0.008(11) -0.019(13) 0.008(16)
C13 0.10(2) 0.09(2) 0.058(16) 0.015(14) 0.009(16) 0.01(2)
C14 0.085(18) 0.073(17) 0.049(13) -0.008(12) 0.014(12) 0.002(15)

_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 I5 2.639(3) . ?
Cu1 I3 2.659(3) . ?
Cu1 I2 2.679(3) . ?
Cu1 I1 2.719(3) . ?
Cu1 Cu4 2.845(4) . ?
Cu2 I6 2.636(3) . ?
Cu2 I2 2.654(3) . ?
Cu2 I1 2.675(3) . ?
Cu2 I4 2.725(3) . ?
Cu2 Cu3 2.873(4) . ?
Cu2 Cu4 3.024(4) . ?
Cu3 I6 2.632(3) 3_646 ?
Cu3 I4 2.664(3) . ?
Cu3 I3 2.689(3) . ?
Cu3 I2 2.712(3) . ?
Cu3 Cu4 3.040(4) . ?
Cu4 I1 2.633(3) . ?
Cu4 I5 2.634(3) 4_566 ?
Cu4 I4 2.695(3) . ?
Cu4 I3 2.712(3) . ?
I5 Cu4 2.634(3) 4_466 ?
I6 Cu3 2.632(3) 3_656 ?
N2 C6 1.12(3) . ?
N4 C13 1.11(4) . ?
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
N1 C7 1.46(3) . ?
C1 C2 1.3900 . ?
C1 H1 0.9400 . ?
C2 C3 1.3900 . ?
C2 H2 0.9400 . ?
C3 C4 1.3900 . ?
C3 C6 1.43(3) . ?
C4 C5 1.3900 . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
N3 C14 1.38(3) . ?
N3 C8 1.3900 . ?
N3 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9400 . ?
C9 C10 1.3900 . ?
C9 H9 0.9400 . ?
C10 C11 1.3900 . ?
C10 C13 1.54(4) . ?
C11 C12 1.3900 . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 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
I5 Cu1 I3 114.52(10) . . ?
I5 Cu1 I2 115.10(11) . . ?
I3 Cu1 I2 104.37(10) . . ?
I5 Cu1 I1 105.26(10) . . ?
I3 Cu1 I1 114.32(11) . . ?
I2 Cu1 I1 102.94(9) . . ?
I5 Cu1 Cu4 138.04(11) . . ?
I3 Cu1 Cu4 58.93(9) . . ?
I2 Cu1 Cu4 106.19(10) . . ?
I1 Cu1 Cu4 56.43(8) . . ?
I6 Cu2 I2 108.49(10) . . ?
I6 Cu2 I1 115.56(11) . . ?
I2 Cu2 I1 104.83(9) . . ?
I6 Cu2 I4 109.33(9) . . ?
I2 Cu2 I4 114.36(11) . . ?
I1 Cu2 I4 104.38(9) . . ?
I6 Cu2 Cu3 136.33(11) . . ?
I2 Cu2 Cu3 58.63(9) . . ?
I1 Cu2 Cu3 108.10(10) . . ?
I4 Cu2 Cu3 56.76(8) . . ?
I6 Cu2 Cu4 149.51(12) . . ?
I2 Cu2 Cu4 102.00(10) . . ?
I1 Cu2 Cu4 54.60(7) . . ?
I4 Cu2 Cu4 55.62(7) . . ?
Cu3 Cu2 Cu4 61.99(9) . . ?
I6 Cu3 I4 115.04(10) 3_646 . ?
I6 Cu3 I3 113.85(10) 3_646 . ?
I4 Cu3 I3 106.04(10) . . ?
I6 Cu3 I2 104.33(10) 3_646 . ?
I4 Cu3 I2 114.42(11) . . ?
I3 Cu3 I2 102.68(9) . . ?
I6 Cu3 Cu2 137.60(11) 3_646 . ?
I4 Cu3 Cu2 58.81(8) . . ?
I3 Cu3 Cu2 107.59(10) . . ?
I2 Cu3 Cu2 56.64(8) . . ?
I6 Cu3 Cu4 155.18(13) 3_646 . ?
I4 Cu3 Cu4 55.93(7) . . ?
I3 Cu3 Cu4 56.12(7) . . ?
I2 Cu3 Cu4 100.22(10) . . ?
Cu2 Cu3 Cu4 61.45(9) . . ?
I1 Cu4 I5 108.90(10) . 4_566 ?
I1 Cu4 I4 106.40(9) . . ?
I5 Cu4 I4 115.62(10) 4_566 . ?
I1 Cu4 I3 115.43(11) . . ?
I5 Cu4 I3 106.23(9) 4_566 . ?
I4 Cu4 I3 104.51(9) . . ?
I1 Cu4 Cu1 59.36(8) . . ?
I5 Cu4 Cu1 134.14(11) 4_566 . ?
I4 Cu4 Cu1 110.10(10) . . ?
I3 Cu4 Cu1 57.12(8) . . ?
I1 Cu4 Cu2 55.94(8) . . ?
I5 Cu4 Cu2 150.89(12) 4_566 . ?
I4 Cu4 Cu2 56.54(7) . . ?
I3 Cu4 Cu2 102.85(10) . . ?
Cu1 Cu4 Cu2 63.69(9) . . ?
I1 Cu4 Cu3 104.54(10) . . ?
I5 Cu4 Cu3 146.47(12) 4_566 . ?
I4 Cu4 Cu3 54.96(7) . . ?
I3 Cu4 Cu3 55.38(7) . . ?
Cu1 Cu4 Cu3 63.77(9) . . ?
Cu2 Cu4 Cu3 56.56(8) . . ?
Cu4 I1 Cu2 69.46(8) . . ?
Cu4 I1 Cu1 64.21(9) . . ?
Cu2 I1 Cu1 70.17(8) . . ?
Cu2 I2 Cu1 71.10(8) . . ?
Cu2 I2 Cu3 64.73(9) . . ?
Cu1 I2 Cu3 70.52(8) . . ?
Cu1 I3 Cu3 71.19(9) . . ?
Cu1 I3 Cu4 63.95(9) . . ?
Cu3 I3 Cu4 68.50(8) . . ?
Cu3 I4 Cu4 69.11(8) . . ?
Cu3 I4 Cu2 64.43(9) . . ?
Cu4 I4 Cu2 67.83(8) . . ?
Cu4 I5 Cu1 123.95(10) 4_466 . ?
Cu3 I6 Cu2 123.81(9) 3_656 . ?
C1 N1 C5 120.0 . . ?
C1 N1 C7 117.0(15) . . ?
C5 N1 C7 123.0(15) . . ?
N1 C1 C2 120.0 . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C6 120.4(13) . . ?
C4 C3 C6 119.4(13) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C5 H5 120.0 . . ?
N2 C6 C3 179(4) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 N3 C8 120.1(14) . . ?
C14 N3 C12 119.9(14) . . ?
C8 N3 C12 120.0 . . ?
N3 C8 C9 120.0 . . ?
N3 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 C13 120.2(14) . . ?
C11 C10 C13 119.5(14) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 N3 120.0 . . ?
C11 C12 H12 120.0 . . ?
N3 C12 H12 120.0 . . ?
N4 C13 C10 176(4) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.264
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.248

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 830728'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N2, Cu I2'
_chemical_formula_sum            'C9 H11 Cu I2 N2'
_chemical_formula_weight         464.55

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'
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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P 42'
_symmetry_space_group_name_Hall  'P 4c'

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

_cell_length_a                   14.015(3)
_cell_length_b                   14.015(3)
_cell_length_c                   6.6579(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1307.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5990
_cell_measurement_theta_min      3.0597
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       Needle
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    6.359
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_T_max  0.564
_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            7522
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2921
_reflns_number_gt                2586
_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^)+(0.0224P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0526
_refine_ls_wR_factor_gt          0.0496
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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 0.0000 1.0000 0.9652(2) 0.0450(2) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.5000 0.9920(3) 0.0509(2) Uani 1 2 d S . .
I1 I -0.09739(2) 0.887817(19) 0.71538(5) 0.03591(9) Uani 1 1 d . . .
I2 I 0.37009(2) 0.57373(2) 1.24158(5) 0.04425(10) Uani 1 1 d . . .
N1 N 0.2489(3) 0.7961(3) 0.7484(8) 0.0459(10) Uani 1 1 d . . .
N2 N 0.1117(5) 0.4467(5) 0.6425(10) 0.095(2) Uani 1 1 d . . .
C1 C 0.1566(3) 0.7834(4) 0.7058(12) 0.0494(13) Uani 1 1 d . . .
H1 H 0.1160 0.8366 0.6963 0.059 Uiso 1 1 calc R . .
C2 C 0.1204(4) 0.6932(4) 0.6756(9) 0.0548(16) Uani 1 1 d . . .
H2 H 0.0554 0.6844 0.6461 0.066 Uiso 1 1 calc R . .
C3 C 0.1810(4) 0.6160(4) 0.6894(9) 0.0547(16) Uani 1 1 d . . .
C4 C 0.2766(4) 0.6306(4) 0.7368(10) 0.0559(13) Uani 1 1 d . . .
H4 H 0.3184 0.5784 0.7480 0.067 Uiso 1 1 calc R . .
C5 C 0.3090(4) 0.7205(4) 0.7668(9) 0.0550(17) Uani 1 1 d . . .
H5 H 0.3733 0.7307 0.8005 0.066 Uiso 1 1 calc R . .
C6 C 0.1438(5) 0.5206(6) 0.6602(10) 0.072(2) Uani 1 1 d . . .
C7 C 0.2856(4) 0.8951(4) 0.7783(10) 0.0599(19) Uani 1 1 d . . .
H7A H 0.3215 0.8979 0.9044 0.072 Uiso 1 1 calc R . .
H7B H 0.2315 0.9391 0.7895 0.072 Uiso 1 1 calc R . .
C8 C 0.3489(5) 0.9267(6) 0.6090(9) 0.073(2) Uani 1 1 d . . .
H8A H 0.3141 0.9231 0.4815 0.088 Uiso 1 1 calc R . .
H8B H 0.4048 0.8849 0.6001 0.088 Uiso 1 1 calc R . .
C9 C 0.3806(4) 1.0300(5) 0.6486(10) 0.077(2) Uani 1 1 d . . .
H9A H 0.3249 1.0709 0.6564 0.115 Uiso 1 1 calc R . .
H9B H 0.4215 1.0513 0.5400 0.115 Uiso 1 1 calc R . .
H9C H 0.4154 1.0329 0.7744 0.115 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 0.0462(10) 0.0424(9) 0.0463(6) 0.000 0.000 -0.0022(9)
Cu2 0.0496(10) 0.0538(10) 0.0493(6) 0.000 0.000 0.0034(9)
I1 0.03586(15) 0.03917(16) 0.03268(18) -0.0026(2) 0.0020(2) -0.00280(11)
I2 0.04517(18) 0.05146(19) 0.0361(2) 0.0020(2) 0.0013(2) 0.00603(13)
N1 0.042(2) 0.064(3) 0.032(3) -0.001(3) 0.004(2) 0.0107(18)
N2 0.132(6) 0.076(4) 0.077(4) -0.006(4) -0.008(4) -0.008(4)
C1 0.041(3) 0.064(3) 0.044(3) 0.008(4) -0.001(3) 0.016(2)
C2 0.047(3) 0.075(4) 0.042(4) 0.002(3) 0.001(3) 0.018(3)
C3 0.068(4) 0.067(4) 0.030(4) -0.002(3) 0.000(3) 0.017(3)
C4 0.061(3) 0.071(4) 0.035(3) 0.002(4) 0.002(4) 0.030(3)
C5 0.042(3) 0.080(4) 0.044(4) 0.001(3) 0.000(3) 0.026(3)
C6 0.075(5) 0.082(5) 0.058(5) -0.003(4) 0.005(3) 0.012(4)
C7 0.055(4) 0.073(4) 0.052(5) 0.006(3) 0.003(3) 0.016(3)
C8 0.048(4) 0.124(7) 0.048(4) 0.005(4) 0.003(3) -0.019(4)
C9 0.050(4) 0.107(6) 0.072(5) 0.031(4) 0.002(3) -0.009(4)

_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 I1 2.6663(12) 4_465 ?
Cu1 I1 2.6663(12) 2_665 ?
Cu1 I1 2.6649(12) . ?
Cu1 I1 2.6649(12) 3_575 ?
Cu1 Cu1 3.329(2) 2_665 ?
Cu1 Cu1 3.329(2) 2_664 ?
Cu2 I2 2.6730(12) 3_665 ?
Cu2 I2 2.6730(12) . ?
Cu2 I2 2.6761(12) 2_654 ?
Cu2 I2 2.6761(12) 4_564 ?
Cu2 Cu2 3.329(3) 2_655 ?
Cu2 Cu2 3.329(3) 2_654 ?
I1 Cu1 2.6663(12) 2_664 ?
I2 Cu2 2.6761(12) 2_655 ?
N1 C1 1.335(6) . ?
N1 C5 1.359(6) . ?
N1 C7 1.493(7) . ?
N2 C6 1.135(8) . ?
C1 C2 1.377(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.379(7) . ?
C2 H2 0.9400 . ?
C3 C4 1.391(7) . ?
C3 C6 1.448(9) . ?
C4 C5 1.354(7) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C7 C8 1.501(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.538(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 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
I1 Cu1 I1 102.68(6) 4_465 2_665 ?
I1 Cu1 I1 112.949(9) 4_465 . ?
I1 Cu1 I1 112.949(9) 2_665 . ?
I1 Cu1 I1 112.949(9) 4_465 3_575 ?
I1 Cu1 I1 112.949(9) 2_665 3_575 ?
I1 Cu1 I1 102.76(6) . 3_575 ?
I1 Cu1 Cu1 51.34(3) 4_465 2_665 ?
I1 Cu1 Cu1 51.34(3) 2_665 2_665 ?
I1 Cu1 Cu1 128.62(3) . 2_665 ?
I1 Cu1 Cu1 128.62(3) 3_575 2_665 ?
I1 Cu1 Cu1 128.66(3) 4_465 2_664 ?
I1 Cu1 Cu1 128.66(3) 2_665 2_664 ?
I1 Cu1 Cu1 51.38(3) . 2_664 ?
I1 Cu1 Cu1 51.38(3) 3_575 2_664 ?
Cu1 Cu1 Cu1 180.000(1) 2_665 2_664 ?
I2 Cu2 I2 103.11(6) 3_665 . ?
I2 Cu2 I2 112.787(9) 3_665 2_654 ?
I2 Cu2 I2 112.787(9) . 2_654 ?
I2 Cu2 I2 112.787(9) 3_665 4_564 ?
I2 Cu2 I2 112.787(9) . 4_564 ?
I2 Cu2 I2 102.94(6) 2_654 4_564 ?
I2 Cu2 Cu2 51.56(3) 3_665 2_655 ?
I2 Cu2 Cu2 51.56(3) . 2_655 ?
I2 Cu2 Cu2 128.53(3) 2_654 2_655 ?
I2 Cu2 Cu2 128.53(3) 4_564 2_655 ?
I2 Cu2 Cu2 128.44(3) 3_665 2_654 ?
I2 Cu2 Cu2 128.44(3) . 2_654 ?
I2 Cu2 Cu2 51.47(3) 2_654 2_654 ?
I2 Cu2 Cu2 51.47(3) 4_564 2_654 ?
Cu2 Cu2 Cu2 180.000(1) 2_655 2_654 ?
Cu1 I1 Cu1 77.280(17) 2_664 . ?
Cu2 I2 Cu2 76.974(18) . 2_655 ?
C1 N1 C5 121.0(5) . . ?
C1 N1 C7 119.1(4) . . ?
C5 N1 C7 119.9(4) . . ?
N1 C1 C2 120.7(4) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 C6 120.9(5) . . ?
C2 C3 C6 119.6(6) . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 N1 120.3(5) . . ?
C4 C5 H5 119.9 . . ?
N1 C5 H5 119.9 . . ?
N2 C6 C3 177.2(8) . . ?
N1 C7 C8 112.2(5) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 108.7(6) . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.090

#===END

data_3
_database_code_depnum_ccdc_archive 'CCDC 830729'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N2, Cu I2'
_chemical_formula_sum            'C9 H11 Cu I2 N2'
_chemical_formula_weight         464.55

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P -4 21 c'
_symmetry_space_group_name_Hall  'P -4 2n'

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

_cell_length_a                   20.190(3)
_cell_length_b                   20.190(3)
_cell_length_c                   6.4628(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2634.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    11006
_cell_measurement_theta_min      3.0268
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       Needle
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    6.313
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.250
_exptl_absorpt_correction_T_max  0.532
_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            12792
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1329
_reflns_number_gt                1296
_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^)+(0.0636P)^2^+13.5755P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         1329
_refine_ls_number_parameters     130
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.017
_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 0.0000 0.5000 0.9677(4) 0.0590(6) Uani 1 2 d S . .
Cu2 Cu 0.0000 1.0000 1.0000 0.0532(9) Uani 1 4 d S . .
Cu3 Cu 0.0000 1.0000 0.5000 0.0552(9) Uani 1 4 d S . .
I1 I 0.10490(4) 0.49055(5) 0.71673(15) 0.0539(3) Uani 1 1 d . . .
I2 I 0.10440(4) 1.00848(4) 0.75014(12) 0.0524(3) Uani 1 1 d . . .
N1 N -0.0184(5) 0.7612(4) 0.7251(16) 0.048(2) Uani 1 1 d U . .
N2 N 0.2316(7) 0.6864(9) 0.785(3) 0.110(5) Uani 1 1 d U . .
C1 C -0.0023(6) 0.6969(6) 0.715(2) 0.055(3) Uani 1 1 d U . .
H1 H -0.0349 0.6642 0.6970 0.066 Uiso 1 1 calc R . .
C2 C 0.0644(6) 0.6800(6) 0.733(2) 0.057(3) Uani 1 1 d U . .
H2 H 0.0771 0.6352 0.7304 0.068 Uiso 1 1 calc R . .
C3 C 0.1096(7) 0.7264(7) 0.752(2) 0.059(3) Uani 1 1 d U . .
C4 C 0.0922(7) 0.7916(7) 0.764(3) 0.067(3) Uani 1 1 d U . .
H4 H 0.1248 0.8243 0.7829 0.080 Uiso 1 1 calc R . .
C5 C 0.0263(7) 0.8090(6) 0.747(2) 0.059(3) Uani 1 1 d U . .
H5 H 0.0133 0.8537 0.7500 0.071 Uiso 1 1 calc R . .
C6 C 0.1785(8) 0.7069(9) 0.776(3) 0.082(4) Uani 1 1 d U . .
C7 C -0.1225(8) 0.7631(9) 0.918(3) 0.085(5) Uani 1 1 d U . .
H7A H -0.1221 0.7154 0.9352 0.127 Uiso 1 1 calc R . .
H7B H -0.1678 0.7790 0.9219 0.127 Uiso 1 1 calc R . .
H7C H -0.0974 0.7834 1.0297 0.127 Uiso 1 1 calc R . .
C8 C -0.0914(7) 0.7810(7) 0.714(3) 0.065(3) Uani 1 1 d U . .
H8 H -0.0936 0.8297 0.6983 0.078 Uiso 1 1 calc R . .
C9 C -0.1226(9) 0.7506(10) 0.525(3) 0.090(5) Uani 1 1 d U . .
H9A H -0.1229 0.7028 0.5389 0.135 Uiso 1 1 calc R . .
H9B H -0.0973 0.7629 0.4031 0.135 Uiso 1 1 calc R . .
H9C H -0.1676 0.7666 0.5107 0.135 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 0.0502(15) 0.0522(16) 0.0745(15) 0.000 0.000 0.0026(8)
Cu2 0.0495(14) 0.0495(14) 0.0607(18) 0.000 0.000 0.000
Cu3 0.0530(14) 0.0530(14) 0.0594(18) 0.000 0.000 0.000
I1 0.0422(5) 0.0627(5) 0.0568(5) 0.0011(4) 0.0001(4) 0.0077(4)
I2 0.0409(5) 0.0730(6) 0.0432(4) 0.0002(5) 0.0004(4) -0.0002(3)
N1 0.060(5) 0.040(5) 0.043(5) -0.004(5) 0.005(5) -0.002(4)
N2 0.079(6) 0.142(9) 0.108(9) 0.011(8) -0.001(7) 0.004(6)
C1 0.046(5) 0.046(5) 0.073(7) 0.000(7) 0.004(7) -0.004(4)
C2 0.053(5) 0.054(6) 0.063(8) 0.001(7) 0.010(7) 0.000(4)
C3 0.055(5) 0.087(7) 0.037(7) 0.010(7) -0.005(7) -0.015(5)
C4 0.074(6) 0.073(6) 0.053(8) -0.003(8) -0.002(8) -0.037(5)
C5 0.088(6) 0.045(5) 0.044(6) 0.002(6) 0.006(7) -0.016(5)
C6 0.066(5) 0.111(8) 0.070(8) 0.010(7) 0.005(7) -0.007(6)
C7 0.069(7) 0.106(9) 0.079(7) 0.000(7) 0.011(6) 0.013(7)
C8 0.069(6) 0.055(7) 0.070(8) -0.004(7) 0.004(7) 0.018(6)
C9 0.080(8) 0.107(9) 0.083(7) -0.008(7) -0.016(6) 0.014(8)

_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 I1 2.6667(18) 8_455 ?
Cu1 I1 2.6668(18) 7 ?
Cu1 I1 2.6746(18) . ?
Cu1 I1 2.6746(18) 2_565 ?
Cu2 I2 2.6608(8) 4_667 ?
Cu2 I2 2.6608(9) 2_575 ?
Cu2 I2 2.6608(9) . ?
Cu2 I2 2.6608(8) 3_467 ?
Cu3 I2 2.6619(8) . ?
Cu3 I2 2.6619(8) 4_666 ?
Cu3 I2 2.6619(8) 3_466 ?
Cu3 I2 2.6619(8) 2_575 ?
I1 Cu1 2.6668(18) 7_554 ?
N1 C5 1.328(14) . ?
N1 C1 1.340(14) . ?
N1 C8 1.530(16) . ?
N2 C6 1.151(18) . ?
C1 C2 1.393(16) . ?
C1 H1 0.9400 . ?
C2 C3 1.313(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.36(2) . ?
C3 C6 1.45(2) . ?
C4 C5 1.381(19) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C7 C8 1.51(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C9 1.50(2) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 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
I1 Cu1 I1 105.77(10) 8_455 7 ?
I1 Cu1 I1 118.64(4) 8_455 . ?
I1 Cu1 I1 104.64(3) 7 . ?
I1 Cu1 I1 104.64(3) 8_455 2_565 ?
I1 Cu1 I1 118.64(4) 7 2_565 ?
I1 Cu1 I1 105.32(10) . 2_565 ?
I2 Cu2 I2 111.612(19) 4_667 2_575 ?
I2 Cu2 I2 111.612(19) 4_667 . ?
I2 Cu2 I2 105.27(4) 2_575 . ?
I2 Cu2 I2 105.27(4) 4_667 3_467 ?
I2 Cu2 I2 111.612(19) 2_575 3_467 ?
I2 Cu2 I2 111.612(19) . 3_467 ?
I2 Cu3 I2 111.644(19) . 4_666 ?
I2 Cu3 I2 111.644(19) . 3_466 ?
I2 Cu3 I2 105.21(4) 4_666 3_466 ?
I2 Cu3 I2 105.21(4) . 2_575 ?
I2 Cu3 I2 111.64(2) 4_666 2_575 ?
I2 Cu3 I2 111.644(19) 3_466 2_575 ?
Cu1 I1 Cu1 74.45(2) 7_554 . ?
Cu2 I2 Cu3 74.76(2) . . ?
C5 N1 C1 123.0(11) . . ?
C5 N1 C8 118.0(10) . . ?
C1 N1 C8 119.0(10) . . ?
N1 C1 C2 117.9(11) . . ?
N1 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 120.3(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.0(13) . . ?
C2 C3 C6 118.8(15) . . ?
C4 C3 C6 120.1(14) . . ?
C3 C4 C5 119.2(11) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 118.6(12) . . ?
N1 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N2 C6 C3 174(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C7 116.1(14) . . ?
C9 C8 N1 109.7(12) . . ?
C7 C8 N1 107.2(13) . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
N1 C8 H8 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.189

#===END

data_4
_database_code_depnum_ccdc_archive 'CCDC 830730'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N, Cu I2'
_chemical_formula_sum            'C7 H9 Cu I2 N'
_chemical_formula_weight         424.50

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           Tetragonal
_symmetry_space_group_name_H-M   'P 42/m n m'
_symmetry_space_group_name_Hall  '-P 4n 2n'

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

_cell_length_a                   12.4720(18)
_cell_length_b                   12.4720(18)
_cell_length_c                   6.7927(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1056.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3438
_cell_measurement_theta_min      3.2646
_cell_measurement_theta_max      25.3491

_exptl_crystal_description       Block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    7.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.175
_exptl_absorpt_correction_T_max  0.317
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication.'

_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 Mercury'
_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            9669
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.35
_reflns_number_total             563
_reflns_number_gt                546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0425P)^2^+1.8635P] 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     SHELXL
_refine_ls_extinction_coef       0.0034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         563
_refine_ls_number_parameters     42
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.000
_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 0.5000 0.0000 -0.7500 0.0447(4) Uani 1 4 d S . .
I1 I 0.57383(4) 0.14773(4) -0.5000 0.0343(3) Uani 1 2 d S . .
C1 C 0.7720(6) -0.0964(7) -0.5000 0.0447(19) Uani 1 2 d S . .
H1 H 0.6990 -0.0780 -0.5000 0.054 Uiso 1 2 calc SR . .
C2 C 0.8497(6) -0.0161(7) -0.5000 0.0420(18) Uani 1 2 d S . .
H2 H 0.8281 0.0561 -0.5000 0.050 Uiso 1 2 calc SR . .
C3 C 0.9593(7) -0.0407(7) -0.5000 0.038(2) Uani 1 4 d S . .
C4 C 0.7163(10) -0.2837(10) -0.571(2) 0.038(4) Uani 0.50 2 d SP . .
H4A H 0.6989 -0.2114 -0.6179 0.046 Uiso 0.25 1 calc PR . .
H4B H 0.7886 -0.3011 -0.6179 0.046 Uiso 0.25 1 calc PR . .
C5 C 0.6729(12) -0.3271(12) -0.379(3) 0.050(5) Uani 0.50 2 d SP . .
H5A H 0.6369 -0.3664 -0.4829 0.075 Uiso 0.50 2 calc SPR . .
H5B H 0.6203 -0.2883 -0.3016 0.075 Uiso 0.25 1 calc PR . .
H5C H 0.7112 -0.3769 -0.2948 0.075 Uiso 0.25 1 calc PR . .
N1 N 0.8008(6) -0.1992(6) -0.5000 0.059(3) Uani 1 4 d S . .

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 0.0429(5) 0.0429(5) 0.0484(8) 0.000 0.000 0.000
I1 0.0330(3) 0.0324(4) 0.0373(4) 0.000 0.000 -0.00020(17)
C1 0.034(4) 0.042(5) 0.058(5) 0.000 0.000 0.015(3)
C2 0.041(4) 0.038(5) 0.047(4) 0.000 0.000 0.017(3)
C3 0.039(3) 0.039(3) 0.036(5) 0.000 0.000 0.014(4)
C4 0.041(5) 0.041(5) 0.033(9) -0.001(5) -0.001(5) 0.010(7)
C5 0.060(7) 0.060(7) 0.030(9) 0.013(6) 0.013(6) 0.009(9)
N1 0.034(3) 0.034(3) 0.110(10) 0.000 0.000 0.001(4)

_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 I1 2.6696(5) . ?
Cu1 I1 2.6696(5) 3_544 ?
Cu1 I1 2.6696(5) 11_664 ?
Cu1 I1 2.6696(5) 9_654 ?
I1 Cu1 2.6696(5) 9_654 ?
C1 N1 1.331(9) . ?
C1 C2 1.394(12) . ?
C1 H1 0.9400 . ?
C2 C3 1.401(9) . ?
C2 H2 0.9400 . ?
C3 C3 1.44(2) 9_754 ?
C3 C2 1.401(9) 7_644 ?
C4 C5 0.84(2) 10_554 ?
C4 C4 0.97(3) 10_554 ?
C4 N1 1.567(19) . ?
C4 C5 1.51(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C4 0.84(2) 10_554 ?
C5 C5 1.64(3) 10_554 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
N1 C1 1.331(9) 7_644 ?
N1 C4 1.567(19) 10_554 ?

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
I1 Cu1 I1 113.869(10) . 3_544 ?
I1 Cu1 I1 113.869(10) . 11_664 ?
I1 Cu1 I1 100.993(19) 3_544 11_664 ?
I1 Cu1 I1 100.993(19) . 9_654 ?
I1 Cu1 I1 113.869(10) 3_544 9_654 ?
I1 Cu1 I1 113.869(10) 11_664 9_654 ?
Cu1 I1 Cu1 79.007(19) . 9_654 ?
N1 C1 C2 120.4(7) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 121.4(8) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C3 C3 C2 122.3(5) 9_754 . ?
C3 C3 C2 122.3(5) 9_754 7_644 ?
C2 C3 C2 115.3(10) . 7_644 ?
C5 C4 C4 113.8(19) 10_554 10_554 ?
C5 C4 N1 174(2) 10_554 . ?
C4 C4 N1 72.0(6) 10_554 . ?
C5 C4 C5 83(3) 10_554 . ?
C4 C4 C5 30.4(9) 10_554 . ?
N1 C4 C5 102.3(10) . . ?
C5 C4 H4A 108.8 10_554 . ?
C4 C4 H4A 108.8 10_554 . ?
N1 C4 H4A 68.3 . . ?
C5 C4 H4A 121.9 . . ?
C5 C4 H4B 108.8 10_554 . ?
C4 C4 H4B 108.8 10_554 . ?
N1 C4 H4B 68.3 . . ?
C5 C4 H4B 121.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C4 35.9(16) 10_554 . ?
C4 C5 C5 66.2(19) 10_554 10_554 ?
C4 C5 C5 30.4(9) . 10_554 ?
C4 C5 H5A 109.5 10_554 . ?
C4 C5 H5A 73.6 . . ?
C5 C5 H5A 43.3 10_554 . ?
C4 C5 H5B 109.5 10_554 . ?
C4 C5 H5B 122.1 . . ?
C5 C5 H5B 122.8 10_554 . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 10_554 . ?
C4 C5 H5C 124.2 . . ?
C5 C5 H5C 126.1 10_554 . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 C1 121.3(10) . 7_644 ?
C1 N1 C4 117.8(5) . 10_554 ?
C1 N1 C4 117.8(5) 7_644 10_554 ?
C1 N1 C4 117.8(5) . . ?
C1 N1 C4 117.8(5) 7_644 . ?
C4 N1 C4 36.1(12) 10_554 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.151
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.143

#===END

data_5
_database_code_depnum_ccdc_archive 'CCDC 830731'
#TrackingRef '- JPLangCIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N, Cu I2'
_chemical_formula_sum            'C8 H11 Cu I2 N'
_chemical_formula_weight         438.52

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           Tetragonal
_symmetry_space_group_name_H-M   'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'

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

_cell_length_a                   17.911(3)
_cell_length_b                   17.911(3)
_cell_length_c                   6.8270(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2190.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7186
_cell_measurement_theta_min      3.1929
_cell_measurement_theta_max      25.3491

_exptl_crystal_description       Block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    7.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1471
_exptl_absorpt_correction_T_max  0.6590
_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            21498
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2003
_reflns_number_gt                1915
_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^)+(0.0314P)^2^+12.2207P] 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     SHELXL
_refine_ls_extinction_coef       0.00141(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2003
_refine_ls_number_parameters     52
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_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 0.7500 -0.2500 -0.2500 0.0404(8) Uani 1 4 d S . .
Cu2 Cu 0.7500 -0.2500 0.2500 0.0446(8) Uani 1 4 d S . .
Cu3 Cu 0.7500 0.2500 0.7100(3) 0.0438(6) Uani 1 2 d S . .
I1 I 0.78170(5) -0.13983(5) -0.00276(8) 0.0334(2) Uani 1 1 d . . .
I2 I 0.78367(5) 0.14027(5) 0.96074(9) 0.0337(2) Uani 1 1 d . . .
C1 C 1.0658(4) 0.3414(4) 0.9733(9) 0.0373(7) Uani 1 1 d G . .
H1 H 1.1110 0.3148 0.9715 0.045 Uiso 1 1 calc R . .
C2 C 1.0663(5) 0.4185(4) 0.9958(9) 0.0373(7) Uani 1 1 d G . .
H2 H 1.1118 0.4441 1.0093 0.045 Uiso 1 1 calc R . .
C3 C 0.9994(6) 0.45786(19) 0.9985(10) 0.0373(7) Uani 1 1 d G . .
C4 C 0.9320(5) 0.4201(4) 0.9786(10) 0.0373(7) Uani 1 1 d G . .
H4 H 0.8868 0.4467 0.9804 0.045 Uiso 1 1 calc R . .
C5 C 0.9315(4) 0.3429(4) 0.9560(9) 0.0373(7) Uani 1 1 d G . .
H5 H 0.8860 0.3174 0.9426 0.045 Uiso 1 1 calc R . .
C6 C 0.9956(6) 0.2235(5) 0.9007(14) 0.0373(7) Uani 1 1 d . . .
H6A H 1.0367 0.2120 0.8108 0.045 Uiso 1 1 calc R . .
H6B H 0.9486 0.2129 0.8329 0.045 Uiso 1 1 calc R . .
C7 C 1.0016(7) 0.1752(5) 1.0772(14) 0.0373(7) Uani 1 1 d . . .
H7A H 0.9577 0.1818 1.1611 0.045 Uiso 1 1 calc R . .
H7B H 1.0462 0.1883 1.1529 0.045 Uiso 1 1 calc R . .
C8 C 1.0066(8) 0.0931(5) 1.0044(16) 0.0373(7) Uani 1 1 d . . .
H8A H 1.0573 0.0824 0.9633 0.056 Uiso 1 1 calc R . .
H8B H 0.9730 0.0861 0.8946 0.056 Uiso 1 1 calc R . .
H8C H 0.9927 0.0596 1.1098 0.056 Uiso 1 1 calc R . .
N1 N 0.9984(5) 0.30361(19) 0.9534(8) 0.0373(7) Uani 1 1 d G . .

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 0.0404(12) 0.0404(12) 0.0403(15) 0.000 0.000 0.000
Cu2 0.0416(12) 0.0416(12) 0.0506(17) 0.000 0.000 0.000
Cu3 0.0414(13) 0.0465(13) 0.0435(11) 0.000 0.000 -0.0009(8)
I1 0.0331(5) 0.0343(5) 0.0329(3) -0.0018(2) 0.0002(3) -0.0026(4)
I2 0.0339(6) 0.0327(5) 0.0344(3) 0.0004(3) -0.0016(3) 0.0009(4)
C1 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C2 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C3 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C4 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C5 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C6 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C7 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
C8 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)
N1 0.0330(14) 0.0365(14) 0.0425(17) 0.0002(14) 0.0017(15) -0.003(2)

_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 I1 2.6580(8) . ?
Cu1 I1 2.6580(8) 2_645 ?
Cu1 I1 2.6580(8) 8_645 ?
Cu1 I1 2.6580(8) 7_665 ?
Cu2 I1 2.6822(8) 2_645 ?
Cu2 I1 2.6822(8) 7_666 ?
Cu2 I1 2.6822(8) 8_646 ?
Cu2 I1 2.6822(8) . ?
Cu3 I2 2.6686(15) 4_564 ?
Cu3 I2 2.6686(15) 3_644 ?
Cu3 I2 2.6755(15) 2_655 ?
Cu3 I2 2.6755(15) . ?
I2 Cu3 2.6686(15) 3_645 ?
C1 C2 1.3900 . ?
C1 N1 1.3900 . ?
C1 H1 0.9400 . ?
C2 C3 1.3900 . ?
C2 H2 0.9400 . ?
C3 C4 1.3900 . ?
C3 C3 1.510(7) 5_767 ?
C4 C5 1.3900 . ?
C4 H4 0.9400 . ?
C5 N1 1.3900 . ?
C5 H5 0.9400 . ?
C6 N1 1.480(9) . ?
C6 C7 1.487(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.555(12) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 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
I1 Cu1 I1 101.16(3) . 2_645 ?
I1 Cu1 I1 113.781(18) . 8_645 ?
I1 Cu1 I1 113.781(18) 2_645 8_645 ?
I1 Cu1 I1 113.781(18) . 7_665 ?
I1 Cu1 I1 113.781(18) 2_645 7_665 ?
I1 Cu1 I1 101.16(3) 8_645 7_665 ?
I1 Cu2 I1 114.452(18) 2_645 7_666 ?
I1 Cu2 I1 114.451(18) 2_645 8_646 ?
I1 Cu2 I1 99.91(3) 7_666 8_646 ?
I1 Cu2 I1 99.91(3) 2_645 . ?
I1 Cu2 I1 114.451(18) 7_666 . ?
I1 Cu2 I1 114.452(18) 8_646 . ?
I2 Cu3 I2 100.78(7) 4_564 3_644 ?
I2 Cu3 I2 114.079(14) 4_564 2_655 ?
I2 Cu3 I2 114.079(15) 3_644 2_655 ?
I2 Cu3 I2 114.079(14) 4_564 . ?
I2 Cu3 I2 114.079(14) 3_644 . ?
I2 Cu3 I2 100.42(7) 2_655 . ?
Cu1 I1 Cu2 79.46(3) . . ?
Cu3 I2 Cu3 79.40(3) 3_645 . ?
C2 C1 N1 120.0 . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C3 120.1(14) . 5_767 ?
C2 C3 C3 119.6(14) . 5_767 ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C5 H5 120.0 . . ?
N1 C6 C7 111.4(7) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 107.2(8) . . ?
C6 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
C6 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 N1 C1 120.0 . . ?
C5 N1 C6 117.7(7) . . ?
C1 N1 C6 121.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.275
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.177

#===END