# 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
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#  data retrieval see:
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data_1

_audit_creation_date             2014-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.25(C128 H168 Cu4 N48 O4), 2(N O3)'
_chemical_formula_sum            'C32 H42 Cu N14 O7'
_chemical_formula_weight         798.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x, -y, -z+1/2'
4 '-x, y, -z+1/2'
5 'x+1/2, y+1/2, z+1/2'
6 '-x+1/2, -y+1/2, z+1/2'
7 'x+1/2, -y+1/2, -z+1'
8 '-x+1/2, y+1/2, -z+1'
9 '-x, -y, -z'
10 'x, y, -z'
11 '-x, y, z-1/2'
12 'x, -y, z-1/2'
13 '-x+1/2, -y+1/2, -z+1/2'
14 'x+1/2, y+1/2, -z+1/2'
15 '-x+1/2, y+1/2, z'
16 'x+1/2, -y+1/2, z'

_cell_length_a                   23.711(5)
_cell_length_b                   8.9025(18)
_cell_length_c                   33.427(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7056(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7722
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.8485
_cell_measurement_theta_min      2.1060
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7633
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             3336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            11583
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 342
	           Slice: -110.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 13.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.2385
	          2theta: -19.8630
;
_diffrn_measurement_device       
;
Saturn724 (4x4 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4574
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1083
_diffrn_orient_matrix_UB_12      -0.0237
_diffrn_orient_matrix_UB_13      0.0181
_diffrn_orient_matrix_UB_21      -0.0006
_diffrn_orient_matrix_UB_22      -0.0239
_diffrn_orient_matrix_UB_23      -0.0347
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      -0.0238
_diffrn_orient_matrix_UB_33      0.0163
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2853
_reflns_number_total             3509
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0741
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0640P)²+22.1470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1752
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
 O4A-N8 \\sim O4B-N8
 with sigma of 0.02
 N9-O5 \\sim N9-O6
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O6) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(N9) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O4B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O5) = Uanis(O6)
4. Others
 Fixed Sof: O4A(0.5) O4B(0.25) O5(0.25) O6(0.5)
 Fixed X: Cu1(0.5) O1(0.5)
 Fixed Y: Cu1(0.5) O1(0.5)
 Fixed Z: O3(0.5) N7(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C9(H9), C10(H10)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.5000 0.62822(2) 0.0451(3) Uani 1 d . . 2 S T P
O1 O 0.5000 0.5000 0.56094(15) 0.0733(15) Uani 1 d . . 2 DS T P
N1 N 0.45242(15) 0.3106(4) 0.62468(10) 0.0462(9) Uani 1 d . . 1 . . .
N2 N 0.4137(2) 0.0887(5) 0.63851(13) 0.0756(14) Uani 1 d . . 1 . . .
N3 N 0.38851(16) 0.1511(4) 0.60616(10) 0.0499(9) Uani 1 d . . 1 . . .
N4 N 0.43001(16) 0.6234(4) 0.64250(11) 0.0487(9) Uani 1 d . . 1 . . .
N5 N 0.34403(17) 0.7269(4) 0.64004(12) 0.0576(10) Uani 1 d . . 1 . . .
N6 N 0.37020(16) 0.7624(4) 0.67496(11) 0.0508(9) Uani 1 d . . 1 . . .
C1 C 0.4516(2) 0.1879(6) 0.64823(15) 0.0675(15) Uani 1 d . . 1 . . .
H1A H 0.4761 0.1751 0.6697 0.081 Uiso 1 calc . . 1 R . .
C2 C 0.41200(19) 0.2816(5) 0.59829(14) 0.0513(11) Uani 1 d . . 1 . . .
H2 H 0.4018 0.3445 0.5773 0.062 Uiso 1 calc . . 1 R . .
C3 C 0.3406(2) 0.0747(6) 0.58653(14) 0.0618(13) Uani 1 d . . 1 . . .
H3A H 0.3057 0.1185 0.5961 0.074 Uiso 1 calc . . 1 R . .
H3B H 0.3408 -0.0305 0.5942 0.074 Uiso 1 calc . . 1 R . .
C4 C 0.34227(19) 0.0857(5) 0.54134(13) 0.0477(11) Uani 1 d . . 1 . . .
C5 C 0.30308(18) 0.1735(5) 0.52091(13) 0.0502(11) Uani 1 d . . 1 . . .
C6 C 0.2598(2) 0.2680(7) 0.54338(18) 0.0781(16) Uani 1 d . . 1 . . .
H6A H 0.2546 0.3619 0.5298 0.117 Uiso 1 calc . . 1 GR . .
H6B H 0.2730 0.2865 0.5701 0.117 Uiso 1 calc . . 1 GR . .
H6C H 0.2246 0.2151 0.5444 0.117 Uiso 1 calc . . 1 GR . .
C7 C 0.38189(19) -0.0018(5) 0.52102(13) 0.0502(11) Uani 1 d . . 1 . . .
C8 C 0.4239(2) -0.0994(6) 0.54301(17) 0.0731(15) Uani 1 d . . 1 . . .
H8A H 0.4150 -0.2032 0.5386 0.110 Uiso 1 calc . . 1 GR . .
H8B H 0.4222 -0.0779 0.5711 0.110 Uiso 1 calc . . 1 GR . .
H8C H 0.4612 -0.0789 0.5333 0.110 Uiso 1 calc . . 1 GR . .
C9 C 0.3815(2) 0.6424(5) 0.62150(13) 0.0518(11) Uani 1 d . . 1 . . .
H9 H 0.3753 0.5999 0.5965 0.062 Uiso 1 calc . . 1 R . .
C10 C 0.4202(2) 0.7010(5) 0.67594(14) 0.0548(12) Uani 1 d . . 1 . . .
H10 H 0.4455 0.7100 0.6970 0.066 Uiso 1 calc . . 1 R . .
C11 C 0.3449(2) 0.8667(5) 0.70446(15) 0.0618(13) Uani 1 d . . 1 . . .
H11A H 0.3324 0.9564 0.6905 0.074 Uiso 1 calc . . 1 R . .
H11B H 0.3738 0.8966 0.7234 0.074 Uiso 1 calc . . 1 R . .
C12 C 0.29520(19) 0.8020(5) 0.72760(13) 0.0467(10) Uani 1 d . . 1 . . .
C13 C 0.2405(2) 0.8295(5) 0.71446(12) 0.0497(11) Uani 1 d . . 1 . . .
C14 C 0.2296(3) 0.9148(7) 0.67578(16) 0.0806(18) Uani 1 d . . 1 . . .
H14A H 0.2240 1.0193 0.6817 0.121 Uiso 1 calc . . 1 GR . .
H14B H 0.1965 0.8752 0.6630 0.121 Uiso 1 calc . . 1 GR . .
H14C H 0.2614 0.9037 0.6583 0.121 Uiso 1 calc . . 1 GR . .
C15 C 0.30518(19) 0.7212(5) 0.76265(13) 0.0503(11) Uani 1 d . . 1 . . .
C16 C 0.3648(2) 0.6898(7) 0.77603(17) 0.0831(18) Uani 1 d . . 1 . . .
H16A H 0.3904 0.7126 0.7546 0.125 Uiso 1 calc . . 1 GR . .
H16B H 0.3683 0.5858 0.7832 0.125 Uiso 1 calc . . 1 GR . .
H16C H 0.3736 0.7512 0.7988 0.125 Uiso 1 calc . . 1 GR . .
O4A O 0.5417(3) 0.0097(15) 0.7289(3) 0.121(4) Uani 0.50 d . 1 1 . . .
O4B O 0.5000 0.0000 0.7154(4) 0.129(6) Uani 0.50 d . 2 2 S TU P
N8 N 0.5000 0.0000 0.7500 0.0520(18) Uani 1 d . . 4 S T P
O2 O 0.63932(18) 0.4787(4) 0.53227(10) 0.0798(11) Uani 1 d . . 1 . . .
O3 O 0.5728(2) 0.5919(7) 0.5000 0.0732(14) Uani 1 d . . 2 S T P
N7 N 0.6173(3) 0.5125(7) 0.5000 0.0581(15) Uani 1 d . . 2 S T P
H1 H 0.477(2) 0.471(7) 0.5434(13) 0.10(2) Uiso 1 d . . 1 D . .
N9 N 0.5000 0.5000 0.2500 0.102(4) Uani 1 d . . 4 S TU P
O5 O 0.5000 0.6525(14) 0.2500 0.110(3) Uani 0.50 d . . 2 S TU P
O6 O 0.5127(4) 0.5371(12) 0.2839(3) 0.110(3) Uani 0.50 d . . 1 . U .


_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 2.249(5) . ?
Cu1 N1 2.032(3) . ?
Cu1 N1 2.032(3) 2_665 ?
Cu1 N4 2.047(4) 2_665 ?
Cu1 N4 2.047(4) . ?
O1 H1 0.84(2) . ?
N1 C1 1.346(6) . ?
N1 C2 1.328(5) . ?
N2 N3 1.354(5) . ?
N2 C1 1.301(6) . ?
N3 C2 1.315(5) . ?
N3 C3 1.478(6) . ?
N4 C9 1.358(6) . ?
N4 C10 1.334(5) . ?
N5 N6 1.359(5) . ?
N5 C9 1.318(6) . ?
N6 C10 1.306(6) . ?
N6 C11 1.481(5) . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.514(6) . ?
C4 C5 1.393(6) . ?
C4 C7 1.397(6) . ?
C5 C5 1.398(9) 10_556 ?
C5 C6 1.525(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C7 1.405(9) 10_556 ?
C7 C8 1.512(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.523(6) . ?
C12 C13 1.392(6) . ?
C12 C15 1.395(6) . ?
C13 C14 1.521(6) . ?
C13 C15 1.400(6) 13_566 ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C13 1.400(6) 13_566 ?
C15 C16 1.509(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O4A O4A 1.42(2) 3_556 ?
O4A N8 1.218(8) . ?
O4B N8 1.158(12) . ?
N8 O4A 1.219(8) 2_655 ?
N8 O4A 1.219(8) 3_556 ?
N8 O4A 1.219(8) 4_656 ?
N8 O4B 1.158(12) 3_556 ?
O2 N7 1.236(4) . ?
O3 N7 1.271(7) . ?
N7 O2 1.236(5) 10_556 ?
N9 O5 1.358(13) 2_665 ?
N9 O5 1.358(13) . ?
N9 O6 1.218(9) 2_665 ?
N9 O6 1.218(9) 3_565 ?
N9 O6 1.218(9) . ?
N9 O6 1.218(9) 4_655 ?
O5 O6 1.559(13) 4_655 ?
O6 O6 0.894(17) 2_665 ?

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 O1 86.67(10) 2_665 . ?
N1 Cu1 O1 86.67(10) . . ?
N1 Cu1 N1 173.3(2) . 2_665 ?
N1 Cu1 N4 90.51(14) 2_665 2_665 ?
N1 Cu1 N4 91.05(14) . 2_665 ?
N1 Cu1 N4 91.05(14) 2_665 . ?
N1 Cu1 N4 90.51(14) . . ?
N4 Cu1 O1 103.49(11) . . ?
N4 Cu1 O1 103.50(11) 2_665 . ?
N4 Cu1 N4 153.0(2) . 2_665 ?
Cu1 O1 H1 134(4) . . ?
C1 N1 Cu1 130.3(3) . . ?
C2 N1 Cu1 126.9(3) . . ?
C2 N1 C1 102.7(4) . . ?
C1 N2 N3 103.0(4) . . ?
N2 N3 C3 120.3(4) . . ?
C2 N3 N2 109.6(4) . . ?
C2 N3 C3 130.1(4) . . ?
C9 N4 Cu1 129.3(3) . . ?
C10 N4 Cu1 127.9(3) . . ?
C10 N4 C9 102.8(4) . . ?
C9 N5 N6 103.2(4) . . ?
N5 N6 C11 122.2(4) . . ?
C10 N6 N5 109.8(4) . . ?
C10 N6 C11 127.8(4) . . ?
N1 C1 H1A 122.8 . . ?
N2 C1 N1 114.5(4) . . ?
N2 C1 H1A 122.8 . . ?
N1 C2 H2 124.9 . . ?
N3 C2 N1 110.2(4) . . ?
N3 C2 H2 124.9 . . ?
N3 C3 H3A 109.0 . . ?
N3 C3 H3B 109.0 . . ?
N3 C3 C4 113.1(4) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 C7 121.6(4) . . ?
C7 C4 C3 117.8(4) . . ?
C4 C5 C5 119.4(3) . 10_556 ?
C4 C5 C6 121.1(4) . . ?
C5 C5 C6 119.5(3) 10_556 . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 C7 119.1(3) . 10_556 ?
C4 C7 C8 121.8(4) . . ?
C7 C7 C8 119.1(3) 10_556 . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9 123.3 . . ?
N5 C9 N4 113.5(4) . . ?
N5 C9 H9 123.3 . . ?
N4 C10 H10 124.6 . . ?
N6 C10 N4 110.7(4) . . ?
N6 C10 H10 124.6 . . ?
N6 C11 H11A 108.6 . . ?
N6 C11 H11B 108.6 . . ?
N6 C11 C12 114.5(4) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 C15 120.9(4) . . ?
C15 C12 C11 119.4(4) . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 C15 119.4(4) . 13_566 ?
C15 C13 C14 119.6(4) 13_566 . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C13 119.6(4) . 13_566 ?
C12 C15 C16 120.2(4) . . ?
C13 C15 C16 120.2(4) 13_566 . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 O4A O4A 54.3(6) . 3_556 ?
O4A N8 O4A 109.3(11) . 2_655 ?
O4A N8 O4A 71.4(11) 4_656 2_655 ?
O4A N8 O4A 109.3(11) 3_556 4_656 ?
O4A N8 O4A 71.4(11) . 3_556 ?
O4A N8 O4A 171.8(13) 3_556 2_655 ?
O4A N8 O4A 171.8(13) . 4_656 ?
O4B N8 O4A 54.6(5) . . ?
O4B N8 O4A 125.4(5) 3_556 2_655 ?
O4B N8 O4A 54.6(5) 3_556 4_656 ?
O4B N8 O4A 54.6(5) . 2_655 ?
O4B N8 O4A 125.4(5) . 3_556 ?
O4B N8 O4A 125.4(5) 3_556 . ?
O4B N8 O4A 125.4(5) . 4_656 ?
O4B N8 O4A 54.6(5) 3_556 3_556 ?
O4B N8 O4B 179.998(1) . 3_556 ?
O2 N7 O2 121.6(7) . 10_556 ?
O2 N7 O3 119.1(3) . . ?
O2 N7 O3 119.1(3) 10_556 . ?
O5 N9 O5 179.999(2) . 2_665 ?
O6 N9 O5 105.7(5) . 2_665 ?
O6 N9 O5 74.3(5) 3_565 2_665 ?
O6 N9 O5 74.3(5) 2_665 2_665 ?
O6 N9 O5 105.7(5) 3_565 . ?
O6 N9 O5 105.7(5) 2_665 . ?
O6 N9 O5 105.7(5) 4_655 2_665 ?
O6 N9 O5 74.3(5) 4_655 . ?
O6 N9 O5 74.3(5) . . ?
O6 N9 O6 151.4(10) 2_665 4_655 ?
O6 N9 O6 151.4(10) 3_565 . ?
O6 N9 O6 43.1(8) 3_565 4_655 ?
O6 N9 O6 148.5(11) 4_655 . ?
O6 N9 O6 43.1(8) 2_665 . ?
O6 N9 O6 148.5(10) 3_565 2_665 ?
N9 O5 O6 48.8(5) . 4_655 ?
O6 O6 N9 68.5(4) 2_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 N2 176.9(4) . . . . ?
Cu1 N1 C2 N3 -177.1(3) . . . . ?
Cu1 N4 C9 N5 178.3(3) . . . . ?
Cu1 N4 C10 N6 -178.2(3) . . . . ?
O1 Cu1 N1 C1 144.9(4) . . . . ?
O1 Cu1 N1 C2 -38.0(4) . . . . ?
O1 Cu1 N4 C9 28.0(4) . . . . ?
O1 Cu1 N4 C10 -154.8(4) . . . . ?
N1 Cu1 N1 C1 144.8(4) 2_665 . . . ?
N1 Cu1 N1 C2 -38.0(4) 2_665 . . . ?
N1 Cu1 N4 C9 114.9(4) 2_665 . . . ?
N1 Cu1 N4 C9 -58.7(4) . . . . ?
N1 Cu1 N4 C10 -68.0(4) 2_665 . . . ?
N1 Cu1 N4 C10 118.5(4) . . . . ?
N2 N3 C2 N1 -0.5(6) . . . . ?
N2 N3 C3 C4 -140.6(5) . . . . ?
N3 N2 C1 N1 0.5(7) . . . . ?
N3 C3 C4 C5 -110.1(5) . . . . ?
N3 C3 C4 C7 73.8(5) . . . . ?
N4 Cu1 N1 C1 -111.7(4) . . . . ?
N4 Cu1 N1 C1 41.4(5) 2_665 . . . ?
N4 Cu1 N1 C2 65.5(4) . . . . ?
N4 Cu1 N1 C2 -141.4(4) 2_665 . . . ?
N4 Cu1 N4 C9 -152.0(4) 2_665 . . . ?
N4 Cu1 N4 C10 25.2(4) 2_665 . . . ?
N5 N6 C10 N4 0.2(5) . . . . ?
N5 N6 C11 C12 73.0(6) . . . . ?
N6 N5 C9 N4 -0.5(5) . . . . ?
N6 C11 C12 C13 -95.3(5) . . . . ?
N6 C11 C12 C15 87.4(5) . . . . ?
C1 N1 C2 N3 0.7(5) . . . . ?
C1 N2 N3 C2 0.0(6) . . . . ?
C1 N2 N3 C3 -177.7(5) . . . . ?
C2 N1 C1 N2 -0.8(6) . . . . ?
C2 N3 C3 C4 42.3(7) . . . . ?
C3 N3 C2 N1 176.9(4) . . . . ?
C3 C4 C5 C5 -175.6(3) . . . 10_556 ?
C3 C4 C5 C6 3.7(6) . . . . ?
C3 C4 C7 C7 175.7(3) . . . 10_556 ?
C3 C4 C7 C8 -2.9(6) . . . . ?
C5 C4 C7 C7 -0.4(5) . . . 10_556 ?
C5 C4 C7 C8 -179.0(4) . . . . ?
C7 C4 C5 C5 0.4(5) . . . 10_556 ?
C7 C4 C5 C6 179.7(4) . . . . ?
C9 N4 C10 N6 -0.5(5) . . . . ?
C9 N5 N6 C10 0.2(5) . . . . ?
C9 N5 N6 C11 175.4(4) . . . . ?
C10 N4 C9 N5 0.6(5) . . . . ?
C10 N6 C11 C12 -112.7(5) . . . . ?
C11 N6 C10 N4 -174.7(4) . . . . ?
C11 C12 C13 C14 4.0(6) . . . . ?
C11 C12 C13 C15 -175.6(4) . . . 13_566 ?
C11 C12 C15 C13 175.6(4) . . . 13_566 ?
C11 C12 C15 C16 -3.9(6) . . . . ?
C13 C12 C15 C13 -1.7(7) . . . 13_566 ?
C13 C12 C15 C16 178.8(4) . . . . ?
C15 C12 C13 C14 -178.7(4) . . . . ?
C15 C12 C13 C15 1.7(7) . . . 13_566 ?
O4A O4A N8 O4A -171.4(14) 3_556 . . 2_655 ?
O4A O4A N8 O4A 95.7(9) 3_556 . . 4_656 ?
O4A O4A N8 O4B 8.6(14) 3_556 . . 3_556 ?
O4A O4A N8 O4B -171.4(14) 3_556 . . . ?
O5 N9 O5 O6 -75.1(5) 2_665 . . 4_655 ?
O5 N9 O6 O6 -44.4(16) 2_665 . . 2_665 ?
O5 N9 O6 O6 135.6(16) . . . 2_665 ?
O6 N9 O5 O6 179.999(3) . . . 4_655 ?
O6 N9 O5 O6 29.7(10) 3_565 . . 4_655 ?
O6 N9 O5 O6 -150.3(10) 2_665 . . 4_655 ?
O6 N9 O6 O6 -130.3(16) 3_565 . . 2_665 ?
O6 N9 O6 O6 135.6(16) 4_655 . . 2_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009806'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            {[Cu(btmx)2(Cl)2]5H2O}n
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H40 Cu N12, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C32 H50 Cl2 Cu N12 O5'
_chemical_formula_weight         817.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9002(16)
_cell_length_b                   10.020(2)
_cell_length_c                   13.153(3)
_cell_angle_alpha                101.72(3)
_cell_angle_beta                 93.69(3)
_cell_angle_gamma                91.54(3)
_cell_volume                     1016.5(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2854
_cell_measurement_theta_min      1.5851
_cell_measurement_theta_max      27.8445

_exptl_crystal_description       rodlike
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             429
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8235
_exptl_absorpt_correction_T_max  0.8692
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Saturn724
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10043
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3775
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0892P)²+0.5882P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3775
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
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
1 -0.020 0.000 0.000 133.6 26.7
2 0.000 0.500 0.500 45.9 1.8
_platon_squeeze_details          
; ?
;
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 0.0000 0.06576(17) Uani 1 2 d S . .
Cl1 Cl 0.32329(12) 0.62693(10) -0.03329(7) 0.0760(3) Uani 1 1 d . . .
O1 O 0.4561(4) 0.9581(4) 0.2033(3) 0.1437(16) Uani 1 1 d . . .
H1WA H 0.4380 0.8747 0.1740 0.172 Uiso 1 1 d R . .
H1WB H 0.4452 1.0101 0.1599 0.172 Uiso 1 1 d R . .
N1 N 0.1110(3) 0.4395(2) 0.12387(16) 0.0501(7) Uani 1 1 d . . .
N2 N 0.2882(3) 0.3783(2) 0.23629(16) 0.0447(6) Uani 1 1 d . . .
N3 N 0.1347(4) 0.3702(4) 0.2739(2) 0.0801(9) Uani 1 1 d . . .
N4 N 0.0569(3) 0.3239(2) -0.09438(16) 0.0476(6) Uani 1 1 d . . .
N5 N 0.0239(3) 0.1375(2) -0.20930(15) 0.0383(5) Uani 1 1 d . . .
N6 N 0.1927(3) 0.1648(2) -0.19647(18) 0.0489(6) Uani 1 1 d . . .
C1 C 0.0334(4) 0.4103(4) 0.2037(3) 0.0788(12) Uani 1 1 d . . .
H1 H -0.0829 0.4175 0.2095 0.095 Uiso 1 1 calc R . .
C2 C 0.2715(4) 0.4189(3) 0.1471(2) 0.0488(8) Uani 1 1 d . . .
H2 H 0.3604 0.4312 0.1064 0.059 Uiso 1 1 calc R . .
C3 C 0.4415(4) 0.3378(3) 0.2901(2) 0.0481(8) Uani 1 1 d . . .
H3A H 0.5391 0.3491 0.2511 0.058 Uiso 1 1 calc R . .
H3B H 0.4293 0.2422 0.2935 0.058 Uiso 1 1 calc R . .
C4 C 0.4707(3) 0.4234(3) 0.39979(18) 0.0354(6) Uani 1 1 d . . .
C5 C 0.5586(3) 0.5484(3) 0.41521(19) 0.0381(6) Uani 1 1 d . . .
C6 C 0.6200(4) 0.6034(3) 0.3244(2) 0.0612(9) Uani 1 1 d . . .
H6A H 0.6043 0.5340 0.2621 0.092 Uiso 1 1 calc R . .
H6B H 0.7382 0.6301 0.3378 0.092 Uiso 1 1 calc R . .
H6C H 0.5563 0.6811 0.3158 0.092 Uiso 1 1 calc R . .
C7 C 0.4114(3) 0.3731(3) 0.4837(2) 0.0380(6) Uani 1 1 d . . .
C8 C 0.3167(4) 0.2368(3) 0.4664(3) 0.0635(9) Uani 1 1 d . . .
H8A H 0.3911 0.1701 0.4852 0.095 Uiso 1 1 calc R . .
H8B H 0.2775 0.2091 0.3943 0.095 Uiso 1 1 calc R . .
H8C H 0.2213 0.2442 0.5086 0.095 Uiso 1 1 calc R . .
C9 C 0.2063(4) 0.2784(3) -0.12635(19) 0.0448(7) Uani 1 1 d . . .
H9 H 0.3098 0.3232 -0.1011 0.054 Uiso 1 1 calc R . .
C10 C -0.0546(4) 0.2332(3) -0.1477(2) 0.0491(8) Uani 1 1 d . . .
H10 H -0.1715 0.2357 -0.1428 0.059 Uiso 1 1 calc R . .
C11 C -0.0525(4) 0.0156(3) -0.28122(19) 0.0426(7) Uani 1 1 d . . .
H11A H -0.1741 0.0130 -0.2747 0.051 Uiso 1 1 calc R . .
H11B H -0.0078 -0.0649 -0.2607 0.051 Uiso 1 1 calc R . .
C12 C -0.0200(3) 0.0104(2) -0.39433(18) 0.0357(6) Uani 1 1 d . . .
C13 C 0.0965(3) -0.0798(2) -0.44304(19) 0.0371(6) Uani 1 1 d . . .
C14 C 0.2000(4) -0.1663(4) -0.3820(2) 0.0654(10) Uani 1 1 d . . .
H14A H 0.1575 -0.2594 -0.4009 0.098 Uiso 1 1 calc R . .
H14B H 0.1911 -0.1330 -0.3088 0.098 Uiso 1 1 calc R . .
H14C H 0.3167 -0.1613 -0.3976 0.098 Uiso 1 1 calc R . .
C15 C -0.1150(3) 0.0906(2) -0.45056(19) 0.0378(6) Uani 1 1 d . . .
C16 C -0.2411(4) 0.1887(3) -0.3971(2) 0.0651(10) Uani 1 1 d . . .
H16A H -0.3018 0.1458 -0.3506 0.098 Uiso 1 1 calc R . .
H16B H -0.3198 0.2126 -0.4485 0.098 Uiso 1 1 calc R . .
H16C H -0.1812 0.2696 -0.3583 0.098 Uiso 1 1 calc R . .


_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 2.009(2) . ?
Cu1 N1 2.009(2) 2_565 ?
Cu1 N4 2.021(2) 2_565 ?
Cu1 N4 2.021(2) . ?
O1 H1WA 0.8500 . ?
O1 H1WB 0.8499 . ?
N1 C2 1.317(4) . ?
N1 C1 1.328(4) . ?
N2 C2 1.318(4) . ?
N2 N3 1.346(4) . ?
N2 C3 1.471(3) . ?
N3 C1 1.314(5) . ?
N4 C10 1.309(4) . ?
N4 C9 1.339(4) . ?
N5 C10 1.320(3) . ?
N5 N6 1.347(3) . ?
N5 C11 1.472(3) . ?
N6 C9 1.308(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.387(4) . ?
C4 C7 1.404(4) . ?
C5 C7 1.403(3) 2_666 ?
C5 C6 1.514(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C5 1.403(3) 2_666 ?
C7 C8 1.508(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.517(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C15 1.400(4) . ?
C12 C13 1.399(4) . ?
C13 C15 1.399(4) 2_554 ?
C13 C14 1.517(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C13 1.399(4) 2_554 ?
C15 C16 1.522(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 180.00(12) . 2_565 ?
N1 Cu1 N4 89.22(9) . 2_565 ?
N1 Cu1 N4 90.78(9) 2_565 2_565 ?
N1 Cu1 N4 90.78(9) . . ?
N1 Cu1 N4 89.22(9) 2_565 . ?
N4 Cu1 N4 180.00(10) 2_565 . ?
H1WA O1 H1WB 111.6 . . ?
C2 N1 C1 103.3(2) . . ?
C2 N1 Cu1 130.5(2) . . ?
C1 N1 Cu1 126.3(2) . . ?
C2 N2 N3 109.4(2) . . ?
C2 N2 C3 129.3(2) . . ?
N3 N2 C3 121.2(2) . . ?
C1 N3 N2 102.8(3) . . ?
C10 N4 C9 104.1(2) . . ?
C10 N4 Cu1 125.0(2) . . ?
C9 N4 Cu1 130.58(19) . . ?
C10 N5 N6 109.7(2) . . ?
C10 N5 C11 127.7(2) . . ?
N6 N5 C11 122.6(2) . . ?
C9 N6 N5 103.0(2) . . ?
N3 C1 N1 114.3(3) . . ?
N3 C1 H1 122.8 . . ?
N1 C1 H1 122.8 . . ?
N1 C2 N2 110.2(3) . . ?
N1 C2 H2 124.9 . . ?
N2 C2 H2 124.9 . . ?
N2 C3 C4 110.9(2) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C7 121.3(2) . . ?
C5 C4 C3 119.3(2) . . ?
C7 C4 C3 119.4(2) . . ?
C4 C5 C7 119.7(2) . 2_666 ?
C4 C5 C6 121.2(2) . . ?
C7 C5 C6 119.1(2) 2_666 . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C4 119.0(2) 2_666 . ?
C5 C7 C8 120.0(2) 2_666 . ?
C4 C7 C8 121.0(2) . . ?
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 . . ?
N6 C9 N4 113.5(2) . . ?
N6 C9 H9 123.2 . . ?
N4 C9 H9 123.2 . . ?
N4 C10 N5 109.7(3) . . ?
N4 C10 H10 125.2 . . ?
N5 C10 H10 125.2 . . ?
N5 C11 C12 113.8(2) . . ?
N5 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N5 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C15 C12 C13 120.7(2) . . ?
C15 C12 C11 119.1(2) . . ?
C13 C12 C11 120.1(2) . . ?
C15 C13 C12 119.1(2) 2_554 . ?
C15 C13 C14 120.2(2) 2_554 . ?
C12 C13 C14 120.7(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C13 120.2(2) . 2_554 ?
C12 C15 C16 120.4(2) . . ?
C13 C15 C16 119.4(2) 2_554 . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C2 154(100) 2_565 . . . ?
N4 Cu1 N1 C2 -113.0(3) 2_565 . . . ?
N4 Cu1 N1 C2 67.0(3) . . . . ?
N1 Cu1 N1 C1 -26(100) 2_565 . . . ?
N4 Cu1 N1 C1 67.1(3) 2_565 . . . ?
N4 Cu1 N1 C1 -112.9(3) . . . . ?
C2 N2 N3 C1 -1.2(4) . . . . ?
C3 N2 N3 C1 -178.1(3) . . . . ?
N1 Cu1 N4 C10 117.4(2) . . . . ?
N1 Cu1 N4 C10 -62.6(2) 2_565 . . . ?
N4 Cu1 N4 C10 -27(100) 2_565 . . . ?
N1 Cu1 N4 C9 -70.6(3) . . . . ?
N1 Cu1 N4 C9 109.4(3) 2_565 . . . ?
N4 Cu1 N4 C9 145(100) 2_565 . . . ?
C10 N5 N6 C9 -0.2(3) . . . . ?
C11 N5 N6 C9 -179.1(2) . . . . ?
N2 N3 C1 N1 1.6(4) . . . . ?
C2 N1 C1 N3 -1.3(4) . . . . ?
Cu1 N1 C1 N3 178.6(2) . . . . ?
C1 N1 C2 N2 0.4(3) . . . . ?
Cu1 N1 C2 N2 -179.47(18) . . . . ?
N3 N2 C2 N1 0.5(3) . . . . ?
C3 N2 C2 N1 177.0(2) . . . . ?
C2 N2 C3 C4 123.7(3) . . . . ?
N3 N2 C3 C4 -60.1(3) . . . . ?
N2 C3 C4 C5 -85.7(3) . . . . ?
N2 C3 C4 C7 95.7(3) . . . . ?
C7 C4 C5 C7 -0.3(4) . . . 2_666 ?
C3 C4 C5 C7 -178.9(2) . . . 2_666 ?
C7 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C5 C4 C7 C5 0.3(4) . . . 2_666 ?
C3 C4 C7 C5 178.9(2) . . . 2_666 ?
C5 C4 C7 C8 -179.7(3) . . . . ?
C3 C4 C7 C8 -1.1(4) . . . . ?
N5 N6 C9 N4 0.1(3) . . . . ?
C10 N4 C9 N6 0.1(3) . . . . ?
Cu1 N4 C9 N6 -173.20(19) . . . . ?
C9 N4 C10 N5 -0.2(3) . . . . ?
Cu1 N4 C10 N5 173.56(18) . . . . ?
N6 N5 C10 N4 0.3(3) . . . . ?
C11 N5 C10 N4 179.1(2) . . . . ?
C10 N5 C11 C12 119.0(3) . . . . ?
N6 N5 C11 C12 -62.3(3) . . . . ?
N5 C11 C12 C15 -77.7(3) . . . . ?
N5 C11 C12 C13 106.1(3) . . . . ?
C15 C12 C13 C15 -1.0(4) . . . 2_554 ?
C11 C12 C13 C15 175.1(2) . . . 2_554 ?
C15 C12 C13 C14 179.8(2) . . . . ?
C11 C12 C13 C14 -4.1(4) . . . . ?
C13 C12 C15 C13 1.0(4) . . . 2_554 ?
C11 C12 C15 C13 -175.1(2) . . . 2_554 ?
C13 C12 C15 C16 -179.9(2) . . . . ?
C11 C12 C15 C16 4.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1009807'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            {[Cu(btmx)(Cl)2]n
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Cl2 Cu N6'
_chemical_formula_sum            'C16 H20 Cl2 Cu N6'
_chemical_formula_weight         430.82

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.328(3)
_cell_length_b                   14.147(3)
_cell_length_c                   9.6681(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.46(3)
_cell_angle_gamma                90.00
_cell_volume                     1786.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884
_exptl_absorpt_coefficient_mu    1.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_T_max  0.7490
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Saturn724
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            17943
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3276
_reflns_number_gt                2937
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0446P)²+9.9377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3276
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.06166(5) 0.09313(5) 0.90187(7) 0.0377(2) Uani 1 1 d . . .
Cl1 Cl 1.09284(12) -0.06702(11) 0.94079(15) 0.0441(4) Uani 1 1 d . . .
Cl2 Cl 1.03046(15) 0.24889(12) 0.86728(18) 0.0600(5) Uani 1 1 d . . .
N1 N 0.8660(4) 0.0871(4) 0.5114(5) 0.0414(12) Uani 1 1 d . . .
N2 N 0.8664(4) -0.0075(4) 0.5351(6) 0.0484(13) Uani 1 1 d . . .
N3 N 0.9727(4) 0.0672(3) 0.7118(5) 0.0399(11) Uani 1 1 d . . .
N4 N 0.2970(4) 0.1136(4) 0.2531(5) 0.0443(12) Uani 1 1 d . . .
N5 N 0.2884(4) 0.2080(4) 0.2243(7) 0.0622(16) Uani 1 1 d . . .
N6 N 0.1766(4) 0.1255(4) 0.0652(5) 0.0414(12) Uani 1 1 d . . .
C1 C 0.9295(5) 0.1303(5) 0.6161(6) 0.0430(15) Uani 1 1 d . . .
H1 H 0.9418 0.1950 0.6216 0.052 Uiso 1 1 calc R . .
C2 C 0.9318(5) -0.0162(4) 0.6559(6) 0.0435(15) Uani 1 1 d . . .
H2 H 0.9486 -0.0743 0.6995 0.052 Uiso 1 1 calc R . .
C3 C 0.8025(5) 0.1295(5) 0.3844(6) 0.0498(17) Uani 1 1 d . . .
H3A H 0.8198 0.1007 0.3012 0.060 Uiso 1 1 calc R . .
H3B H 0.8177 0.1965 0.3822 0.060 Uiso 1 1 calc R . .
C4 C 0.6881(4) 0.1166(4) 0.3805(6) 0.0368(13) Uani 1 1 d . . .
C5 C 0.6349(5) 0.0433(4) 0.3003(6) 0.0392(13) Uani 1 1 d . . .
C6 C 0.5305(5) 0.0333(4) 0.2961(6) 0.0412(14) Uani 1 1 d . . .
C7 C 0.4804(4) 0.0947(4) 0.3742(6) 0.0396(14) Uani 1 1 d . . .
C8 C 0.5336(5) 0.1695(5) 0.4523(6) 0.0435(15) Uani 1 1 d . . .
C9 C 0.6389(5) 0.1798(4) 0.4555(6) 0.0411(14) Uani 1 1 d . . .
C10 C 0.6974(5) 0.2587(5) 0.5422(8) 0.065(2) Uani 1 1 d . . .
H10A H 0.7661 0.2607 0.5259 0.098 Uiso 1 1 calc R . .
H10B H 0.6991 0.2474 0.6406 0.098 Uiso 1 1 calc R . .
H10C H 0.6642 0.3179 0.5152 0.098 Uiso 1 1 calc R . .
C11 C 0.4779(6) 0.2399(5) 0.5292(8) 0.0616(19) Uani 1 1 d . . .
H11A H 0.4104 0.2508 0.4749 0.092 Uiso 1 1 calc R . .
H11B H 0.5151 0.2984 0.5413 0.092 Uiso 1 1 calc R . .
H11C H 0.4731 0.2149 0.6200 0.092 Uiso 1 1 calc R . .
C12 C 0.4697(5) -0.0439(5) 0.2065(7) 0.0595(19) Uani 1 1 d . . .
H12A H 0.4523 -0.0234 0.1101 0.089 Uiso 1 1 calc R . .
H12B H 0.4082 -0.0567 0.2407 0.089 Uiso 1 1 calc R . .
H12C H 0.5104 -0.1004 0.2123 0.089 Uiso 1 1 calc R . .
C13 C 0.6886(5) -0.0261(5) 0.2208(7) 0.0554(17) Uani 1 1 d . . .
H13A H 0.6546 -0.0862 0.2159 0.083 Uiso 1 1 calc R . .
H13B H 0.7585 -0.0333 0.2690 0.083 Uiso 1 1 calc R . .
H13C H 0.6869 -0.0029 0.1270 0.083 Uiso 1 1 calc R . .
C14 C 0.3684(5) 0.0783(5) 0.3783(7) 0.0496(16) Uani 1 1 d . . .
H14A H 0.3572 0.0111 0.3874 0.060 Uiso 1 1 calc R . .
H14B H 0.3532 0.1091 0.4614 0.060 Uiso 1 1 calc R . .
C15 C 0.2308(5) 0.0663(5) 0.1582(6) 0.0455(15) Uani 1 1 d . . .
H15 H 0.2231 0.0009 0.1566 0.055 Uiso 1 1 calc R . .
C16 C 0.2145(5) 0.2107(5) 0.1134(7) 0.0552(18) Uani 1 1 d . . .
H16 H 0.1895 0.2671 0.0706 0.066 Uiso 1 1 calc R . .


_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 N3 2.013(5) . ?
Cu1 N6 2.023(5) 1_656 ?
Cu1 Cl2 2.2550(18) . ?
Cu1 Cl1 2.3207(17) . ?
N1 C1 1.332(7) . ?
N1 N2 1.359(7) . ?
N1 C3 1.473(7) . ?
N2 C2 1.317(8) . ?
N3 C1 1.332(7) . ?
N3 C2 1.366(8) . ?
N4 C15 1.322(8) . ?
N4 N5 1.364(8) . ?
N4 C14 1.471(7) . ?
N5 C16 1.305(8) . ?
N6 C15 1.331(8) . ?
N6 C16 1.353(8) . ?
N6 Cu1 2.023(5) 1_454 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.528(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.395(8) . ?
C4 C5 1.400(8) . ?
C5 C6 1.390(8) . ?
C5 C13 1.512(9) . ?
C6 C7 1.404(9) . ?
C6 C12 1.524(9) . ?
C7 C8 1.407(8) . ?
C7 C14 1.519(8) . ?
C8 C9 1.405(9) . ?
C8 C11 1.521(9) . ?
C9 C10 1.516(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
N3 Cu1 N6 166.3(2) . 1_656 ?
N3 Cu1 Cl2 89.14(15) . . ?
N6 Cu1 Cl2 89.05(16) 1_656 . ?
N3 Cu1 Cl1 91.37(15) . . ?
N6 Cu1 Cl1 90.63(15) 1_656 . ?
Cl2 Cu1 Cl1 179.09(7) . . ?
C1 N1 N2 110.1(5) . . ?
C1 N1 C3 128.3(5) . . ?
N2 N1 C3 121.6(5) . . ?
C2 N2 N1 102.8(5) . . ?
C1 N3 C2 102.8(5) . . ?
C1 N3 Cu1 127.4(4) . . ?
C2 N3 Cu1 129.4(4) . . ?
C15 N4 N5 109.7(5) . . ?
C15 N4 C14 129.3(6) . . ?
N5 N4 C14 121.0(5) . . ?
C16 N5 N4 102.4(5) . . ?
C15 N6 C16 102.3(5) . . ?
C15 N6 Cu1 127.6(4) . 1_454 ?
C16 N6 Cu1 130.0(4) . 1_454 ?
N1 C1 N3 110.0(6) . . ?
N1 C1 H1 125.0 . . ?
N3 C1 H1 125.0 . . ?
N2 C2 N3 114.3(6) . . ?
N2 C2 H2 122.8 . . ?
N3 C2 H2 122.8 . . ?
N1 C3 C4 112.1(5) . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C9 C4 C5 121.6(5) . . ?
C9 C4 C3 118.7(6) . . ?
C5 C4 C3 119.8(6) . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 C13 119.5(6) . . ?
C4 C5 C13 121.5(6) . . ?
C5 C6 C7 120.1(5) . . ?
C5 C6 C12 120.3(6) . . ?
C7 C6 C12 119.6(6) . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 C14 119.6(6) . . ?
C6 C7 C14 119.6(5) . . ?
C9 C8 C7 119.0(6) . . ?
C9 C8 C11 120.3(6) . . ?
C7 C8 C11 120.7(6) . . ?
C4 C9 C8 119.6(5) . . ?
C4 C9 C10 121.1(6) . . ?
C8 C9 C10 119.3(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C7 113.9(5) . . ?
N4 C14 H14A 108.8 . . ?
C7 C14 H14A 108.8 . . ?
N4 C14 H14B 108.8 . . ?
C7 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N4 C15 N6 110.3(6) . . ?
N4 C15 H15 124.8 . . ?
N6 C15 H15 124.8 . . ?
N5 C16 N6 115.2(6) . . ?
N5 C16 H16 122.4 . . ?
N6 C16 H16 122.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.0(7) . . . . ?
C3 N1 N2 C2 179.6(5) . . . . ?
N6 Cu1 N3 C1 -76.8(10) 1_656 . . . ?
Cl2 Cu1 N3 C1 5.6(5) . . . . ?
Cl1 Cu1 N3 C1 -175.1(5) . . . . ?
N6 Cu1 N3 C2 112.0(9) 1_656 . . . ?
Cl2 Cu1 N3 C2 -165.6(5) . . . . ?
Cl1 Cu1 N3 C2 13.7(5) . . . . ?
C15 N4 N5 C16 1.3(8) . . . . ?
C14 N4 N5 C16 -175.9(6) . . . . ?
N2 N1 C1 N3 -0.5(7) . . . . ?
C3 N1 C1 N3 179.9(5) . . . . ?
C2 N3 C1 N1 0.8(7) . . . . ?
Cu1 N3 C1 N1 -172.2(4) . . . . ?
N1 N2 C2 N3 0.5(7) . . . . ?
C1 N3 C2 N2 -0.8(7) . . . . ?
Cu1 N3 C2 N2 172.0(4) . . . . ?
C1 N1 C3 C4 -116.2(7) . . . . ?
N2 N1 C3 C4 64.3(8) . . . . ?
N1 C3 C4 C9 82.8(7) . . . . ?
N1 C3 C4 C5 -98.4(6) . . . . ?
C9 C4 C5 C6 -0.3(8) . . . . ?
C3 C4 C5 C6 -179.1(5) . . . . ?
C9 C4 C5 C13 -179.0(5) . . . . ?
C3 C4 C5 C13 2.2(8) . . . . ?
C4 C5 C6 C7 -1.5(8) . . . . ?
C13 C5 C6 C7 177.3(5) . . . . ?
C4 C5 C6 C12 178.3(5) . . . . ?
C13 C5 C6 C12 -3.0(9) . . . . ?
C5 C6 C7 C8 2.9(8) . . . . ?
C12 C6 C7 C8 -176.9(6) . . . . ?
C5 C6 C7 C14 -175.1(5) . . . . ?
C12 C6 C7 C14 5.2(8) . . . . ?
C6 C7 C8 C9 -2.5(8) . . . . ?
C14 C7 C8 C9 175.5(5) . . . . ?
C6 C7 C8 C11 176.0(6) . . . . ?
C14 C7 C8 C11 -6.0(9) . . . . ?
C5 C4 C9 C8 0.7(8) . . . . ?
C3 C4 C9 C8 179.5(5) . . . . ?
C5 C4 C9 C10 179.9(6) . . . . ?
C3 C4 C9 C10 -1.4(8) . . . . ?
C7 C8 C9 C4 0.7(8) . . . . ?
C11 C8 C9 C4 -177.8(6) . . . . ?
C7 C8 C9 C10 -178.5(6) . . . . ?
C11 C8 C9 C10 3.0(9) . . . . ?
C15 N4 C14 C7 117.5(7) . . . . ?
N5 N4 C14 C7 -65.9(8) . . . . ?
C8 C7 C14 N4 101.7(7) . . . . ?
C6 C7 C14 N4 -80.3(7) . . . . ?
N5 N4 C15 N6 -0.2(7) . . . . ?
C14 N4 C15 N6 176.7(6) . . . . ?
C16 N6 C15 N4 -1.0(7) . . . . ?
Cu1 N6 C15 N4 -177.7(4) 1_454 . . . ?
N4 N5 C16 N6 -2.0(8) . . . . ?
C15 N6 C16 N5 1.9(8) . . . . ?
Cu1 N6 C16 N5 178.5(5) 1_454 . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 1009808'
