# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_H2-1,3-bdpb


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            1,3-bis(3,5-dimethyl-1H-pyrazol-4-yl)benzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4, C H4 O'
_chemical_formula_sum            'C17 H22 N4 O'
_chemical_formula_weight         298.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/m 1'

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

_cell_length_a                   4.7416(3)
_cell_length_b                   12.1325(7)
_cell_length_c                   14.0001(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.107(2)
_cell_angle_gamma                90.00
_cell_volume                     802.19(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4381
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      26.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16984
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.36
_reflns_number_total             1705
_reflns_number_gt                1411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Word

_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)+(0.0324P)²+0.5270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1705
_refine_ls_number_parameters     110
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.120
_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
O1 O 0.1107(4) 0.2500 0.54743(12) 0.0173(4) Uani 1 2 d SU A 1
H1 H 0.0910 0.1975 0.5854 0.026 Uiso 0.50 1 calc PR A 1
N1 N 0.9585(3) 0.41065(12) 0.67382(10) 0.0194(4) Uani 1 1 d U . 1
H1A H 1.0273 0.3745 0.6266 0.023 Uiso 0.50 1 calc PR . 1
N2 N 0.7800(3) 0.36848(12) 0.73523(10) 0.0195(4) Uani 1 1 d U . 1
H2 H 0.7133 0.3008 0.7342 0.023 Uiso 0.50 1 calc PR . 1
C1 C 0.7225(4) 0.44725(13) 0.79769(12) 0.0155(4) Uani 1 1 d U . 1
C2 C 0.8668(4) 0.54354(13) 0.77625(12) 0.0135(4) Uani 1 1 d U . 1
C3 C 1.0128(4) 0.51605(13) 0.69674(12) 0.0147(4) Uani 1 1 d U . 1
C4 C 1.2077(4) 0.58256(14) 0.64140(12) 0.0182(4) Uani 1 1 d U . 1
H4A H 1.3371 0.5332 0.6112 0.027 Uiso 1 1 calc R . 1
H4B H 1.3173 0.6331 0.6849 0.027 Uiso 1 1 calc R . 1
H4C H 1.0967 0.6251 0.5918 0.027 Uiso 1 1 calc R . 1
C5 C 0.5215(4) 0.42467(14) 0.87203(12) 0.0179(4) Uani 1 1 d U . 1
H5A H 0.3755 0.3729 0.8462 0.027 Uiso 1 1 calc R . 1
H5B H 0.4321 0.4937 0.8895 0.027 Uiso 1 1 calc R . 1
H5C H 0.6255 0.3926 0.9290 0.027 Uiso 1 1 calc R . 1
C6 C 0.8710(3) 0.64949(13) 0.82777(12) 0.0135(4) Uani 1 1 d U . 1
C7 C 0.8636(5) 0.7500 0.77947(17) 0.0137(5) Uani 1 2 d SU . 1
H7 H 0.8532 0.7500 0.7114 0.016 Uiso 1 2 calc SR . 1
C8 C 0.8851(4) 0.65102(14) 0.92822(12) 0.0163(4) Uani 1 1 d U . 1
H8 H 0.8904 0.5835 0.9627 0.020 Uiso 1 1 calc R . 1
C9 C 0.8915(5) 0.7500 0.97749(17) 0.0171(5) Uani 1 2 d SU . 1
H9 H 0.9002 0.7500 1.0455 0.021 Uiso 1 2 calc SR . 1
C10 C 0.3906(6) 0.2500 0.5196(2) 0.0291(7) Uani 1 2 d SU A 1
H10A H 0.3926 0.2159 0.4562 0.044 Uiso 0.50 1 calc PR A 1
H10B H 0.5137 0.2081 0.5664 0.044 Uiso 0.50 1 calc PR A 1
H10C H 0.4594 0.3260 0.5170 0.044 Uiso 0.50 1 calc PR A 1

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
O1 0.0201(10) 0.0145(9) 0.0184(9) 0.000 0.0077(7) 0.000
N1 0.0288(9) 0.0135(7) 0.0168(8) 0.0000(6) 0.0073(6) -0.0017(6)
N2 0.0292(9) 0.0103(7) 0.0198(8) 0.0013(6) 0.0081(6) -0.0001(6)
C1 0.0179(9) 0.0114(8) 0.0175(9) 0.0007(7) 0.0022(7) 0.0020(7)
C2 0.0148(9) 0.0112(8) 0.0142(8) 0.0024(6) -0.0004(7) 0.0016(6)
C3 0.0162(9) 0.0126(8) 0.0151(8) 0.0018(7) 0.0000(7) 0.0021(7)
C4 0.0204(10) 0.0160(9) 0.0187(9) 0.0014(7) 0.0045(7) 0.0006(7)
C5 0.0203(9) 0.0146(9) 0.0194(9) 0.0014(7) 0.0047(7) -0.0014(7)
C6 0.0109(9) 0.0123(8) 0.0174(9) -0.0006(7) 0.0013(7) 0.0001(6)
C7 0.0124(12) 0.0148(12) 0.0140(12) 0.000 0.0017(9) 0.000
C8 0.0195(9) 0.0120(9) 0.0174(9) 0.0037(7) 0.0015(7) 0.0000(7)
C9 0.0223(14) 0.0169(12) 0.0120(12) 0.000 0.0011(10) 0.000
C10 0.0237(16) 0.0426(17) 0.0220(14) 0.000 0.0083(12) 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
O1 C10 1.416(3) . ?
O1 H1 0.8400 . ?
N1 C3 1.338(2) . ?
N1 N2 1.3591(19) . ?
N1 H1A 0.8800 . ?
N2 C1 1.340(2) . ?
N2 H2 0.8800 . ?
C1 C2 1.400(2) . ?
C1 C5 1.498(2) . ?
C2 C3 1.402(2) . ?
C2 C6 1.473(2) . ?
C3 C4 1.495(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.393(2) . ?
C6 C8 1.402(2) . ?
C7 C6 1.393(2) 4_575 ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C8 1.384(2) 4_575 ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C3 N1 N2 109.00(14) . . ?
C3 N1 H1A 125.5 . . ?
N2 N1 H1A 125.5 . . ?
C1 N2 N1 108.59(14) . . ?
C1 N2 H2 125.7 . . ?
N1 N2 H2 125.7 . . ?
N2 C1 C2 108.88(15) . . ?
N2 C1 C5 120.15(15) . . ?
C2 C1 C5 130.92(15) . . ?
C1 C2 C3 104.89(14) . . ?
C1 C2 C6 127.51(15) . . ?
C3 C2 C6 127.58(15) . . ?
N1 C3 C2 108.64(14) . . ?
N1 C3 C4 120.43(15) . . ?
C2 C3 C4 130.91(15) . . ?
C7 C6 C8 118.18(16) . . ?
C7 C6 C2 121.83(15) . . ?
C8 C6 C2 119.99(14) . . ?
C6 C7 C6 122.1(2) . 4_575 ?
C6 C7 H7 118.9 . . ?
C6 C7 H7 118.9 4_575 . ?
C9 C8 C6 120.56(16) . . ?
C9 C8 H8 119.7 . . ?
C6 C8 H8 119.7 . . ?
C8 C9 C8 120.4(2) . 4_575 ?
C8 C9 H9 119.8 . . ?
C8 C9 H9 119.8 4_575 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1006742'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CFA-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cu2 N4 O2'
_chemical_formula_weight         453.48

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'
Cu Cu 0.3201 1.2651 '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           Trigonal
_symmetry_space_group_name_H-M   'R -3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   26.839(3)
_cell_length_b                   26.839(3)
_cell_length_c                   15.8317(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     9876.2(19)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2068
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.77

_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4176
_exptl_absorpt_coefficient_mu    1.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19551
_diffrn_reflns_av_R_equivalents  0.1439
_diffrn_reflns_av_sigmaI/netI    0.1131
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3874
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Word

_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. 
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.002 489 84 ' '
2 0.004 0.307 0.030 9 1 ' '
3 -0.004 0.693 0.970 9 2 ' '
4 0.026 0.364 0.696 8 1 ' '
5 0.030 0.670 0.637 8 1 ' '
6 0.333 0.667 0.216 488 84 ' '
7 0.303 -0.004 0.030 9 1 ' '
8 0.307 0.303 0.970 9 1 ' '
9 0.330 0.360 0.637 8 1 ' '
10 0.337 0.973 0.696 8 1 ' '
11 0.360 0.030 0.363 9 1 ' '
12 0.364 0.337 0.304 8 1 ' '
13 0.667 0.333 0.882 488 84 ' '
14 0.636 0.663 0.696 8 1 ' '
15 0.640 0.970 0.637 9 1 ' '
16 0.663 0.026 0.304 8 1 ' '
17 0.670 0.640 0.363 9 1 ' '
18 0.693 0.697 0.030 9 1 ' '
19 0.697 0.004 0.970 9 1 ' '
20 0.970 0.330 0.363 8 1 ' '
21 0.973 0.636 0.304 8 1 ' '
_platon_squeeze_details          
;
The electron count (271 electrons) corresponds to the 15 MeOH molecules. 
;

_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)+(0.0679P)²+9.8837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3874
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.52510(4) 0.60906(3) 0.11769(5) 0.0136(2) Uani 1 1 d . . .
Cu2 Cu 0.58112(4) 0.74897(3) 0.13017(5) 0.0134(2) Uani 1 1 d . . .
O1 O 0.5715(2) 0.67963(18) 0.1782(3) 0.0184(11) Uani 1 1 d . . .
O2 O 0.4469(2) 0.5473(2) 0.1035(3) 0.0223(12) Uani 1 1 d . . .
N1 N 0.5323(2) 0.6525(2) 0.0172(3) 0.0151(13) Uani 1 1 d . . .
N2 N 0.5485(2) 0.7092(2) 0.0229(3) 0.0113(12) Uani 1 1 d . . .
N3 N 0.6394(2) 0.8259(2) 0.0962(3) 0.0102(12) Uani 1 1 d . . .
N4 N 0.5380(2) 0.5593(2) 0.1908(3) 0.0128(12) Uani 1 1 d . . .
C1 C 0.5187(3) 0.6359(3) -0.0632(4) 0.0178(16) Uani 1 1 d . . .
C2 C 0.5244(3) 0.6816(3) -0.1116(4) 0.0132(15) Uani 1 1 d . . .
C3 C 0.5432(3) 0.7271(3) -0.0544(4) 0.0155(15) Uani 1 1 d . . .
C4 C 0.5020(4) 0.5760(3) -0.0910(5) 0.031(2) Uani 1 1 d . . .
H4A H 0.5026 0.5538 -0.0423 0.046 Uiso 1 1 calc R . .
H4B H 0.5293 0.5779 -0.1337 0.046 Uiso 1 1 calc R . .
H4C H 0.4632 0.5574 -0.1151 0.046 Uiso 1 1 calc R . .
C5 C 0.5538(3) 0.7868(3) -0.0711(5) 0.0258(18) Uani 1 1 d . . .
H5A H 0.5387 0.7990 -0.0239 0.039 Uiso 1 1 calc R . .
H5B H 0.5343 0.7868 -0.1234 0.039 Uiso 1 1 calc R . .
H5C H 0.5952 0.8134 -0.0768 0.039 Uiso 1 1 calc R . .
C6 C 0.5173(3) 0.6828(3) -0.2041(4) 0.0131(15) Uani 1 1 d . . .
C7 C 0.4655(3) 0.6453(3) -0.2452(4) 0.0152(15) Uani 1 1 d . . .
H7 H 0.4324 0.6199 -0.2135 0.018 Uiso 1 1 calc R . .
C8 C 0.4633(3) 0.6460(3) -0.3327(4) 0.0152(15) Uani 1 1 d . . .
H8 H 0.4285 0.6198 -0.3605 0.018 Uiso 1 1 calc R . .
C9 C 0.6847(3) 0.8460(3) 0.0424(4) 0.0129(7) Uani 1 1 d . . .
C10 C 0.6932(3) 0.8069(3) -0.0141(4) 0.0129(7) Uani 1 1 d . . .
H10A H 0.7203 0.7971 0.0120 0.019 Uiso 1 1 calc R . .
H10B H 0.7087 0.8259 -0.0684 0.019 Uiso 1 1 calc R . .
H10C H 0.6563 0.7716 -0.0233 0.019 Uiso 1 1 calc R . .
C11 C 0.7201(3) 0.9053(3) 0.0552(4) 0.0129(7) Uani 1 1 d . . .
C12 C 0.7714(3) 0.9450(3) 0.0069(4) 0.0129(7) Uani 1 1 d . . .
C13 C 0.7688(3) 0.9463(3) -0.0810(4) 0.0129(7) Uani 1 1 d . . .
H13 H 0.7338 0.9206 -0.1086 0.016 Uiso 1 1 calc R . .
C14 C 0.8233(3) 0.9832(3) 0.0470(4) 0.0104(14) Uani 1 1 d . . .
H14 H 0.8262 0.9831 0.1068 0.013 Uiso 1 1 calc R . .
C15 C 0.5853(3) 0.5591(3) 0.2141(4) 0.0167(16) Uani 1 1 d . . .
C16 C 0.6423(3) 0.5978(3) 0.1727(5) 0.0253(18) Uani 1 1 d . . .
H16A H 0.6483 0.5772 0.1265 0.038 Uiso 1 1 calc R . .
H16B H 0.6731 0.6097 0.2144 0.038 Uiso 1 1 calc R . .
H16C H 0.6424 0.6320 0.1503 0.038 Uiso 1 1 calc R . .
C17 C 0.5926(5) 0.6825(5) 0.2626(6) 0.068(2) Uani 1 1 d . . .
H17A H 0.5961 0.7164 0.2914 0.103 Uiso 1 1 calc R . .
H17B H 0.6304 0.6852 0.2602 0.103 Uiso 1 1 calc R . .
H17C H 0.5657 0.6477 0.2938 0.103 Uiso 1 1 calc R . .
C18 C 0.4041(5) 0.5640(5) 0.0680(7) 0.068(2) Uani 1 1 d . . .
H18A H 0.4203 0.5875 0.0172 0.103 Uiso 1 1 calc R . .
H18B H 0.3967 0.5860 0.1105 0.103 Uiso 1 1 calc R . .
H18C H 0.3680 0.5291 0.0537 0.103 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 0.0187(5) 0.0129(5) 0.0072(4) 0.0031(3) -0.0008(3) 0.0063(4)
Cu2 0.0207(5) 0.0113(5) 0.0073(4) 0.0004(3) 0.0014(3) 0.0073(4)
O1 0.034(3) 0.009(2) 0.012(3) 0.0036(19) -0.004(2) 0.011(2)
O2 0.017(3) 0.028(3) 0.014(3) 0.009(2) -0.003(2) 0.004(2)
N1 0.026(3) 0.012(3) 0.005(3) 0.003(2) 0.001(2) 0.008(3)
N2 0.020(3) 0.010(3) 0.004(3) 0.000(2) 0.001(2) 0.008(3)
N3 0.012(3) 0.014(3) 0.006(3) -0.004(2) -0.003(2) 0.007(3)
N4 0.009(3) 0.009(3) 0.012(3) 0.005(2) -0.003(2) -0.002(3)
C1 0.025(4) 0.019(4) 0.008(4) 0.002(3) 0.003(3) 0.010(3)
C2 0.018(4) 0.011(4) 0.008(3) -0.001(3) -0.003(3) 0.006(3)
C3 0.019(4) 0.012(4) 0.013(4) 0.004(3) 0.001(3) 0.006(3)
C4 0.057(6) 0.020(4) 0.012(4) -0.001(3) -0.003(4) 0.018(4)
C5 0.046(5) 0.014(4) 0.018(4) -0.002(3) -0.006(4) 0.016(4)
C6 0.025(4) 0.006(3) 0.008(3) 0.003(3) 0.002(3) 0.007(3)
C7 0.021(4) 0.014(4) 0.011(4) 0.003(3) 0.002(3) 0.009(3)
C8 0.013(4) 0.013(4) 0.015(4) 0.002(3) -0.002(3) 0.003(3)
C9 0.0168(17) 0.0151(17) 0.0083(15) -0.0004(12) 0.0008(12) 0.0090(14)
C10 0.0168(17) 0.0151(17) 0.0083(15) -0.0004(12) 0.0008(12) 0.0090(14)
C11 0.0168(17) 0.0151(17) 0.0083(15) -0.0004(12) 0.0008(12) 0.0090(14)
C12 0.0168(17) 0.0151(17) 0.0083(15) -0.0004(12) 0.0008(12) 0.0090(14)
C13 0.0168(17) 0.0151(17) 0.0083(15) -0.0004(12) 0.0008(12) 0.0090(14)
C14 0.019(4) 0.006(3) 0.007(3) 0.002(3) 0.002(3) 0.007(3)
C15 0.016(4) 0.011(4) 0.018(4) 0.004(3) -0.003(3) 0.003(3)
C16 0.014(4) 0.031(5) 0.026(4) 0.014(3) 0.000(3) 0.008(4)
C17 0.085(6) 0.058(5) 0.053(5) 0.007(4) -0.006(4) 0.029(5)
C18 0.085(6) 0.058(5) 0.053(5) 0.007(4) -0.006(4) 0.029(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 O1 1.923(4) . ?
Cu1 N4 1.924(5) . ?
Cu1 N1 1.925(5) . ?
Cu1 O2 1.929(5) . ?
Cu2 O1 1.904(4) . ?
Cu2 O2 1.921(4) 15 ?
Cu2 N3 1.942(5) . ?
Cu2 N2 1.963(5) . ?
O1 C17 1.439(11) . ?
O2 C18 1.531(11) . ?
O2 Cu2 1.921(4) 14_455 ?
N1 C1 1.337(8) . ?
N1 N2 1.359(7) . ?
N2 C3 1.349(8) . ?
N3 C9 1.355(8) . ?
N3 N4 1.363(7) 15 ?
N4 C15 1.326(8) . ?
N4 N3 1.363(7) 14_455 ?
C1 C2 1.386(9) . ?
C1 C4 1.502(9) . ?
C2 C3 1.396(9) . ?
C2 C6 1.480(9) . ?
C3 C5 1.504(9) . ?
C6 C13 1.388(9) 16_664 ?
C6 C7 1.403(9) . ?
C7 C8 1.387(9) . ?
C8 C14 1.375(9) 16_664 ?
C9 C11 1.402(9) . ?
C9 C10 1.481(9) . ?
C11 C15 1.396(9) 15 ?
C11 C12 1.466(9) . ?
C12 C13 1.394(9) . ?
C12 C14 1.403(9) . ?
C13 C6 1.388(9) 16_664 ?
C14 C8 1.375(9) 16_664 ?
C15 C11 1.396(9) 14_455 ?
C15 C16 1.503(9) . ?

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 Cu1 N4 97.5(2) . . ?
O1 Cu1 N1 89.7(2) . . ?
N4 Cu1 N1 156.9(2) . . ?
O1 Cu1 O2 142.6(2) . . ?
N4 Cu1 O2 88.3(2) . . ?
N1 Cu1 O2 99.2(2) . . ?
O1 Cu2 O2 98.2(2) . 15 ?
O1 Cu2 N3 142.5(2) . . ?
O2 Cu2 N3 89.8(2) 15 . ?
O1 Cu2 N2 90.5(2) . . ?
O2 Cu2 N2 144.6(2) 15 . ?
N3 Cu2 N2 104.0(2) . . ?
C17 O1 Cu2 117.5(5) . . ?
C17 O1 Cu1 124.0(5) . . ?
Cu2 O1 Cu1 117.9(2) . . ?
C18 O2 Cu2 109.9(5) . 14_455 ?
C18 O2 Cu1 116.4(5) . . ?
Cu2 O2 Cu1 113.3(2) 14_455 . ?
C1 N1 N2 108.6(5) . . ?
C1 N1 Cu1 131.0(5) . . ?
N2 N1 Cu1 120.1(4) . . ?
C3 N2 N1 107.8(5) . . ?
C3 N2 Cu2 133.6(4) . . ?
N1 N2 Cu2 118.2(4) . . ?
C9 N3 N4 107.6(5) . 15 ?
C9 N3 Cu2 133.1(4) . . ?
N4 N3 Cu2 118.2(4) 15 . ?
C15 N4 N3 109.4(5) . 14_455 ?
C15 N4 Cu1 132.5(4) . . ?
N3 N4 Cu1 117.6(4) 14_455 . ?
N1 C1 C2 109.8(6) . . ?
N1 C1 C4 121.4(6) . . ?
C2 C1 C4 128.7(6) . . ?
C1 C2 C3 104.3(6) . . ?
C1 C2 C6 127.4(6) . . ?
C3 C2 C6 128.0(6) . . ?
N2 C3 C2 109.4(6) . . ?
N2 C3 C5 122.8(6) . . ?
C2 C3 C5 127.7(6) . . ?
C13 C6 C7 118.8(6) 16_664 . ?
C13 C6 C2 118.7(6) 16_664 . ?
C7 C6 C2 122.4(6) . . ?
C8 C7 C6 119.2(6) . . ?
C14 C8 C7 121.8(6) 16_664 . ?
N3 C9 C11 109.0(6) . . ?
N3 C9 C10 121.5(6) . . ?
C11 C9 C10 129.4(6) . . ?
C15 C11 C9 104.6(6) 15 . ?
C15 C11 C12 127.9(6) 15 . ?
C9 C11 C12 127.3(6) . . ?
C13 C12 C14 118.5(6) . . ?
C13 C12 C11 119.9(6) . . ?
C14 C12 C11 121.5(6) . . ?
C6 C13 C12 121.9(6) 16_664 . ?
C8 C14 C12 119.7(6) 16_664 . ?
N4 C15 C11 109.5(6) . 14_455 ?
N4 C15 C16 121.4(6) . . ?
C11 C15 C16 129.2(6) 14_455 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 1006743'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CuICl(H2-1,3-bdpb)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl Cu N4'
_chemical_formula_weight         365.33

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'
Cl Cl 0.1484 0.1585 '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 m a'

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

_cell_length_a                   6.1784(8)
_cell_length_b                   12.9041(17)
_cell_length_c                   19.866(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1583.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7845
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      31.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12815
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1460
_reflns_number_gt                1265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Word

_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)+(0.0571P)²+3.2042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1460
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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 0.66323(11) 1.2500 0.67777(3) 0.0353(3) Uani 1 2 d S . .
Cl1 Cl 1.0474(2) 1.2500 0.69987(6) 0.0311(3) Uani 1 2 d S . .
N1 N 0.5750(5) 1.1085(2) 0.65284(15) 0.0309(7) Uani 1 1 d . . .
C1 C 0.3707(6) 0.9660(3) 0.66173(19) 0.0309(8) Uani 1 1 d . . .
N2 N 0.3993(5) 1.0645(2) 0.68183(16) 0.0334(7) Uani 1 1 d . . .
H2 H 0.3139 1.0966 0.7105 0.040 Uiso 1 1 calc R . .
C2 C 0.5384(6) 0.9435(2) 0.61793(17) 0.0266(7) Uani 1 1 d . . .
C3 C 0.6595(5) 1.0358(3) 0.61398(17) 0.0274(8) Uani 1 1 d . . .
C4 C 0.1825(7) 0.9044(3) 0.6867(2) 0.0465(11) Uani 1 1 d . . .
H4A H 0.0963 0.9469 0.7176 0.070 Uiso 1 1 calc R . .
H4B H 0.2352 0.8428 0.7104 0.070 Uiso 1 1 calc R . .
H4C H 0.0926 0.8831 0.6485 0.070 Uiso 1 1 calc R . .
C5 C 0.8557(6) 1.0598(3) 0.5731(2) 0.0413(10) Uani 1 1 d . . .
H5A H 0.9014 1.1313 0.5817 0.062 Uiso 1 1 calc R . .
H5B H 0.8219 1.0516 0.5252 0.062 Uiso 1 1 calc R . .
H5C H 0.9728 1.0122 0.5854 0.062 Uiso 1 1 calc R . .
C6 C 0.5766(6) 0.8444(2) 0.58297(17) 0.0269(7) Uani 1 1 d . . .
C7 C 0.6403(6) 0.8431(3) 0.51533(18) 0.0329(8) Uani 1 1 d . . .
H7 H 0.6611 0.9066 0.4920 0.040 Uiso 1 1 calc R . .
C8 C 0.5497(8) 0.7500 0.6157(2) 0.0268(10) Uani 1 2 d S . .
H8 H 0.5115 0.7500 0.6621 0.032 Uiso 1 2 calc SR . .
C9 C 0.6730(9) 0.7500 0.4823(3) 0.0365(13) Uani 1 2 d S . .
H9 H 0.7182 0.7500 0.4366 0.044 Uiso 1 2 calc SR . .

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 0.0469(5) 0.0176(4) 0.0416(4) 0.000 0.0004(3) 0.000
Cl1 0.0307(6) 0.0295(6) 0.0333(7) 0.000 -0.0008(5) 0.000
N1 0.0368(16) 0.0190(14) 0.0370(16) -0.0020(13) 0.0032(14) -0.0008(13)
C1 0.0346(19) 0.0203(17) 0.038(2) 0.0001(15) 0.0042(16) 0.0004(15)
N2 0.0393(17) 0.0206(15) 0.0402(18) -0.0057(13) 0.0111(14) 0.0013(13)
C2 0.0352(19) 0.0154(15) 0.0293(18) 0.0012(13) -0.0006(15) 0.0008(14)
C3 0.0353(19) 0.0200(16) 0.0268(17) -0.0004(14) 0.0000(14) 0.0020(15)
C4 0.043(2) 0.032(2) 0.065(3) -0.0034(19) 0.016(2) -0.0054(18)
C5 0.045(2) 0.034(2) 0.045(2) -0.0051(18) 0.0109(18) -0.0105(18)
C6 0.0342(18) 0.0180(16) 0.0286(18) -0.0019(14) -0.0013(14) -0.0005(15)
C7 0.048(2) 0.0213(17) 0.0295(19) 0.0029(14) 0.0004(16) -0.0017(16)
C8 0.034(3) 0.023(2) 0.024(2) 0.000 0.004(2) 0.000
C9 0.053(3) 0.027(3) 0.029(3) 0.000 0.004(2) 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
Cu1 N1 1.969(3) . ?
Cu1 N1 1.969(3) 7_585 ?
Cu1 Cl1 2.4136(15) . ?
Cu1 Cl1 2.5340(14) 2_476 ?
Cl1 Cu1 2.5340(14) 2_576 ?
N1 C3 1.322(4) . ?
N1 N2 1.353(4) . ?
C1 N2 1.344(5) . ?
C1 C2 1.384(5) . ?
C1 C4 1.493(5) . ?
N2 H2 0.8800 . ?
C2 C3 1.409(5) . ?
C2 C6 1.474(4) . ?
C3 C5 1.492(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.391(4) . ?
C6 C7 1.400(5) . ?
C7 C9 1.385(4) . ?
C7 H7 0.9500 . ?
C8 C6 1.391(4) 7_575 ?
C8 H8 0.9500 . ?
C9 C7 1.385(4) 7_575 ?
C9 H9 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 136.08(18) . 7_585 ?
N1 Cu1 Cl1 108.54(9) . . ?
N1 Cu1 Cl1 108.54(9) 7_585 . ?
N1 Cu1 Cl1 99.38(9) . 2_476 ?
N1 Cu1 Cl1 99.38(9) 7_585 2_476 ?
Cl1 Cu1 Cl1 95.93(4) . 2_476 ?
Cu1 Cl1 Cu1 116.89(5) . 2_576 ?
C3 N1 N2 105.5(3) . . ?
C3 N1 Cu1 134.1(3) . . ?
N2 N1 Cu1 120.2(2) . . ?
N2 C1 C2 106.7(3) . . ?
N2 C1 C4 120.5(3) . . ?
C2 C1 C4 132.8(3) . . ?
C1 N2 N1 112.1(3) . . ?
C1 N2 H2 124.0 . . ?
N1 N2 H2 124.0 . . ?
C1 C2 C3 104.8(3) . . ?
C1 C2 C6 126.8(3) . . ?
C3 C2 C6 128.4(3) . . ?
N1 C3 C2 110.9(3) . . ?
N1 C3 C5 119.4(3) . . ?
C2 C3 C5 129.6(3) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 118.2(3) . . ?
C8 C6 C2 121.3(3) . . ?
C7 C6 C2 120.5(3) . . ?
C9 C7 C6 120.4(3) . . ?
C9 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6 C8 C6 122.2(4) 7_575 . ?
C6 C8 H8 118.9 7_575 . ?
C6 C8 H8 118.9 . . ?
C7 C9 C7 120.5(5) 7_575 . ?
C7 C9 H9 119.8 7_575 . ?
C7 C9 H9 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 1006744'
