# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'William Gee'
'Stuart Batten'
_publ_contact_author_email       stuart.batten@sci.monash.edu.au
_publ_contact_author_name        'Stuart Batten'

data_c:\CuGel
_database_code_depnum_ccdc_archive 'CCDC 862495'
#TrackingRef '- 1.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl2 Cu N6'
_chemical_formula_sum            'C16 H14 Cl2 Cu N6'
_chemical_formula_weight         424.77

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'
N N 0.0061 0.0033 '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'
Cu Cu 0.3201 1.2651 '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 n n m'

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

_cell_length_a                   3.7720(8)
_cell_length_b                   10.381(2)
_cell_length_c                   20.876(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     817.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    13606
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.78

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.710698
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Australian synchrotron MX1'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'scans in phi'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            13606
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         29.38
_reflns_number_total             1136
_reflns_number_gt                1071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu-Ice (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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^)+(0.0978P)^2^+3.2279P] 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         1136
_refine_ls_number_parameters     56
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.0000 0.0000 0.0000 0.0269(3) Uani 1 4 d S . .
Cl1 Cl -0.3718(4) -0.17715(11) 0.0000 0.0254(4) Uani 1 2 d S . .
C2 C 0.1038(10) -0.1083(3) 0.19535(17) 0.0235(7) Uani 1 1 d . . .
H2 H 0.1786 -0.1842 0.2170 0.028 Uiso 1 1 calc R . .
C3 C 0.0000 0.0000 0.2304(2) 0.0222(9) Uani 1 2 d S . .
N1 N 0.0000 0.0000 0.0960(2) 0.0249(9) Uani 1 2 d S . .
C1 C 0.0973(11) -0.1048(3) 0.12921(17) 0.0250(7) Uani 1 1 d . . .
H1 H 0.1647 -0.1799 0.1062 0.030 Uiso 1 1 calc R . .
C4 C 0.0000 0.0000 0.3001(2) 0.0280(11) Uani 1 2 d S . .
C5 C 0.0946(14) -0.1049(6) 0.3365(2) 0.0560(11) Uani 0.50 1 d P A 1
H5 H 0.1698 -0.1872 0.3220 0.067 Uiso 0.50 1 calc PR A 1
C6 C 0.0567(14) -0.0645(6) 0.3972(2) 0.0560(11) Uani 0.50 1 d P . 1
H6 H 0.0997 -0.1151 0.4343 0.067 Uiso 0.50 1 calc PR . 1
N2 N 0.0946(14) -0.1049(6) 0.3365(2) 0.0560(11) Uani 0.50 1 d P A 2
N3 N 0.0567(14) -0.0645(6) 0.3972(2) 0.0560(11) Uani 0.50 1 d P . 2
H3 H 0.0965 -0.1114 0.4316 0.067 Uiso 0.50 1 calc PR . 2

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 0.0426(6) 0.0241(5) 0.0141(5) 0.000 0.000 -0.0108(4)
Cl1 0.0345(7) 0.0242(6) 0.0174(5) 0.000 0.000 -0.0050(4)
C2 0.0307(17) 0.0206(14) 0.0192(15) 0.0014(11) 0.0000(13) -0.0002(13)
C3 0.024(2) 0.024(2) 0.019(2) 0.000 0.000 -0.0031(16)
N1 0.036(2) 0.0216(19) 0.0169(18) 0.000 0.000 -0.0042(16)
C1 0.0341(18) 0.0219(15) 0.0190(15) -0.0018(11) 0.0014(14) -0.0003(14)
C4 0.033(3) 0.032(3) 0.018(2) 0.000 0.000 -0.003(2)
C5 0.0462(19) 0.084(3) 0.0374(17) 0.0332(18) -0.0041(14) -0.0058(18)
C6 0.0462(19) 0.084(3) 0.0374(17) 0.0332(18) -0.0041(14) -0.0058(18)
N2 0.0462(19) 0.084(3) 0.0374(17) 0.0332(18) -0.0041(14) -0.0058(18)
N3 0.0462(19) 0.084(3) 0.0374(17) 0.0332(18) -0.0041(14) -0.0058(18)

_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 N1 2.004(4) . ?
Cu1 N1 2.004(4) 5 ?
Cu1 Cl1 2.3126(12) . ?
Cu1 Cl1 2.3126(12) 5 ?
C2 C1 1.382(5) . ?
C2 C3 1.398(4) . ?
C2 H2 0.9500 . ?
C3 C2 1.398(4) 2 ?
C3 C4 1.455(7) . ?
N1 C1 1.341(4) . ?
N1 C1 1.341(4) 2 ?
C1 H1 0.9500 . ?
C4 C5 1.375(6) . ?
C4 N2 1.375(6) 2 ?
C4 C5 1.375(6) 2 ?
C5 C6 1.343(8) . ?
C5 H5 0.9500 . ?
C6 C6 1.405(13) 2 ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.0 . 5 ?
N1 Cu1 Cl1 90.0 . . ?
N1 Cu1 Cl1 90.0 5 . ?
N1 Cu1 Cl1 90.0 . 5 ?
N1 Cu1 Cl1 90.0 5 5 ?
Cl1 Cu1 Cl1 180.00(3) . 5 ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C2 116.9(4) . 2 ?
C2 C3 C4 121.6(2) . . ?
C2 C3 C4 121.6(2) 2 . ?
C1 N1 C1 117.8(4) . 2 ?
C1 N1 Cu1 121.1(2) . . ?
C1 N1 Cu1 121.1(2) 2 . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C5 C4 N2 112.9(6) . 2 ?
C5 C4 C5 112.9(6) . 2 ?
C5 C4 C3 123.5(3) . . ?
N2 C4 C3 123.5(3) 2 . ?
C5 C4 C3 123.5(3) 2 . ?
C6 C5 C4 104.3(6) . . ?
C6 C5 H5 127.9 . . ?
C4 C5 H5 127.9 . . ?
C5 C6 C6 109.3(3) . 2 ?
C5 C6 H6 125.4 . . ?
C6 C6 H6 125.4 2 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 Cl1 0.88 2.62 3.446(5) 156.2 3_545

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        29.38
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         1.474
_refine_diff_density_min         -1.501
_refine_diff_density_rms         0.144