# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wb2ck
_database_code_depnum_ccdc_archive 'CCDC 1006215'
_audit_update_record             
;
2014-06-02 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Br Cu N2'
_chemical_formula_sum            'C20 H24 Br Cu N2'
_chemical_formula_weight         435.86

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'
Br Br -0.2901 2.4595 '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 b c a'
_symmetry_int_tables_number      61

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

_cell_length_a                   9.6421(3)
_cell_length_b                   19.6933(5)
_cell_length_c                   19.7231(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3745.12(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18336
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.83

_exptl_crystal_description       block
_exptl_crystal_colour            'dark orange'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    3.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 The collected data cover nominally a full sphere of the reciprocal space.
 A combination of 24 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 1.0 deg in ω.
 Each frame was exposured for 5s. Nominal crystal to detector distance 45 mm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            143456
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5456
_reflns_number_gt                4443
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    
;
 SHELXS-97 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)
;
_computing_structure_refinement  
;
 SHELXL-97 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)
;
_computing_publication_material  
;
 WinGX v1.80.05 (L. J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838.)
;

_refine_special_details          
;
 All H atoms were refined using a riding model, with a common U restrained
 to be 1.2 (1.5 for methyl groups) times the equivalent isotropic displacement
 parameter of the parent atom. Methyl groups were treated as rigid bodies and
 allowed to rotate about the E-CH3 bond.

 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)+(0.0226P)²+4.2970P] 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         5456
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.33744(2) 0.178034(10) 0.604964(10) 0.02103(6) Uani 1 1 d . . .
Cu1 Cu 0.15934(2) 0.103087(11) 0.624683(11) 0.01464(6) Uani 1 1 d . . .
N2 N 0.13521(15) -0.00189(7) 0.63222(7) 0.0108(3) Uani 1 1 d . . .
N1 N -0.05191(16) 0.09955(7) 0.60787(7) 0.0125(3) Uani 1 1 d . . .
C10 C 0.22219(18) -0.05144(9) 0.65102(8) 0.0121(3) Uani 1 1 d . . .
C9 C 0.1951(2) -0.11984(9) 0.63290(10) 0.0163(4) Uani 1 1 d . . .
H9 H 0.2575 -0.1546 0.6464 0.020 Uiso 1 1 calc R . .
C17 C 0.35287(19) -0.03183(9) 0.69026(9) 0.0144(3) Uani 1 1 d . . .
C18 C 0.3244(2) 0.02477(10) 0.74199(10) 0.0195(4) Uani 1 1 d . . .
H18A H 0.4111 0.0374 0.7646 0.029 Uiso 1 1 calc R . .
H18B H 0.2576 0.0086 0.7758 0.029 Uiso 1 1 calc R . .
H18C H 0.2862 0.0645 0.7186 0.029 Uiso 1 1 calc R . .
C2 C -0.2741(2) 0.13634(10) 0.56868(10) 0.0217(4) Uani 1 1 d . . .
H2 H -0.3400 0.1719 0.5642 0.026 Uiso 1 1 calc R . .
C11 C -0.2336(2) -0.04791(10) 0.52863(9) 0.0175(4) Uani 1 1 d . . .
H11 H -0.3163 -0.0578 0.5045 0.021 Uiso 1 1 calc R . .
C4 C -0.20721(19) 0.02031(10) 0.55090(9) 0.0154(4) Uani 1 1 d . . .
C1 C -0.1472(2) 0.14846(9) 0.60294(9) 0.0157(4) Uani 1 1 d . . .
C5 C -0.08190(18) 0.03586(9) 0.58462(8) 0.0124(3) Uani 1 1 d . . .
C13 C -0.1158(2) 0.21811(10) 0.63423(10) 0.0201(4) Uani 1 1 d . . .
C6 C 0.01636(18) -0.01792(9) 0.59811(8) 0.0111(3) Uani 1 1 d . . .
C7 C -0.01596(19) -0.08497(9) 0.57809(9) 0.0135(3) Uani 1 1 d . . .
C16 C -0.0303(3) 0.21092(10) 0.69941(10) 0.0256(5) Uani 1 1 d . . .
H16A H -0.0794 0.1813 0.7313 0.038 Uiso 1 1 calc R . .
H16B H -0.0171 0.2558 0.7200 0.038 Uiso 1 1 calc R . .
H16C H 0.0603 0.1911 0.6886 0.038 Uiso 1 1 calc R . .
C12 C -0.1420(2) -0.09818(10) 0.54169(9) 0.0171(4) Uani 1 1 d . . .
H12 H -0.1613 -0.1430 0.5265 0.021 Uiso 1 1 calc R . .
C15 C -0.0365(2) 0.26018(10) 0.58106(10) 0.0253(4) Uani 1 1 d . . .
H15A H 0.0524 0.2382 0.5711 0.038 Uiso 1 1 calc R . .
H15B H -0.0198 0.3059 0.5988 0.038 Uiso 1 1 calc R . .
H15C H -0.0917 0.2632 0.5394 0.038 Uiso 1 1 calc R . .
C3 C -0.3018(2) 0.07385(11) 0.54213(10) 0.0205(4) Uani 1 1 d . . .
H3 H -0.3853 0.0665 0.5176 0.025 Uiso 1 1 calc R . .
C19 C 0.4136(2) -0.09235(11) 0.72930(11) 0.0276(5) Uani 1 1 d . . .
H19A H 0.4937 -0.0772 0.7559 0.041 Uiso 1 1 calc R . .
H19B H 0.4430 -0.1275 0.6971 0.041 Uiso 1 1 calc R . .
H19C H 0.3429 -0.1110 0.7598 0.041 Uiso 1 1 calc R . .
C8 C 0.0790(2) -0.13592(9) 0.59603(9) 0.0160(4) Uani 1 1 d . . .
H8 H 0.0629 -0.1816 0.5826 0.019 Uiso 1 1 calc R . .
C20 C 0.4610(2) -0.00721(12) 0.63845(10) 0.0245(4) Uani 1 1 d . . .
H20A H 0.4248 0.0325 0.6143 0.037 Uiso 1 1 calc R . .
H20B H 0.4804 -0.0436 0.6060 0.037 Uiso 1 1 calc R . .
H20C H 0.5467 0.0052 0.6621 0.037 Uiso 1 1 calc R . .
C14 C -0.2512(3) 0.25496(12) 0.65269(14) 0.0377(6) Uani 1 1 d . . .
H14A H -0.3043 0.2641 0.6113 0.056 Uiso 1 1 calc R . .
H14B H -0.2294 0.2979 0.6754 0.056 Uiso 1 1 calc R . .
H14C H -0.3062 0.2263 0.6831 0.056 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br1 Cu1 2.2975(3) . ?
Cu1 N1 2.0649(16) . ?
Cu1 N2 2.0857(14) . ?
N2 C10 1.339(2) . ?
N2 C6 1.366(2) . ?
N1 C1 1.335(2) . ?
N1 C5 1.367(2) . ?
C10 C9 1.418(2) . ?
C10 C17 1.528(2) . ?
C9 C8 1.371(3) . ?
C9 H9 0.9500 . ?
C17 C19 1.535(3) . ?
C17 C18 1.536(3) . ?
C17 C20 1.538(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C2 C3 1.364(3) . ?
C2 C1 1.417(3) . ?
C2 H2 0.9500 . ?
C11 C12 1.351(3) . ?
C11 C4 1.436(3) . ?
C11 H11 0.9500 . ?
C4 C3 1.405(3) . ?
C4 C5 1.413(2) . ?
C1 C13 1.534(3) . ?
C5 C6 1.446(2) . ?
C13 C16 1.534(3) . ?
C13 C14 1.538(3) . ?
C13 C15 1.539(3) . ?
C6 C7 1.413(2) . ?
C7 C8 1.404(3) . ?
C7 C12 1.435(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C8 H8 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 Cu1 N2 82.41(6) . . ?
N1 Cu1 Br1 137.04(4) . . ?
N2 Cu1 Br1 137.07(4) . . ?
C10 N2 C6 119.57(15) . . ?
C10 N2 Cu1 132.23(12) . . ?
C6 N2 Cu1 106.71(11) . . ?
C1 N1 C5 119.48(16) . . ?
C1 N1 Cu1 131.80(13) . . ?
C5 N1 Cu1 107.07(11) . . ?
N2 C10 C9 120.46(16) . . ?
N2 C10 C17 118.19(15) . . ?
C9 C10 C17 121.32(16) . . ?
C8 C9 C10 120.23(17) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C17 C19 111.85(16) . . ?
C10 C17 C18 111.86(15) . . ?
C19 C17 C18 107.37(16) . . ?
C10 C17 C20 107.58(14) . . ?
C19 C17 C20 108.63(17) . . ?
C18 C17 C20 109.50(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C2 C1 120.27(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C12 C11 C4 120.75(17) . . ?
C12 C11 H11 119.6 . . ?
C4 C11 H11 119.6 . . ?
C3 C4 C5 116.78(17) . . ?
C3 C4 C11 123.35(18) . . ?
C5 C4 C11 119.87(17) . . ?
N1 C1 C2 120.48(18) . . ?
N1 C1 C13 118.67(17) . . ?
C2 C1 C13 120.85(17) . . ?
N1 C5 C4 122.54(16) . . ?
N1 C5 C6 118.16(16) . . ?
C4 C5 C6 119.24(16) . . ?
C16 C13 C1 111.15(15) . . ?
C16 C13 C14 107.55(18) . . ?
C1 C13 C14 110.44(18) . . ?
C16 C13 C15 110.73(18) . . ?
C1 C13 C15 107.76(16) . . ?
C14 C13 C15 109.21(17) . . ?
N2 C6 C7 122.59(16) . . ?
N2 C6 C5 118.11(15) . . ?
C7 C6 C5 119.25(16) . . ?
C8 C7 C6 116.97(16) . . ?
C8 C7 C12 123.30(17) . . ?
C6 C7 C12 119.72(17) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 C7 121.06(17) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 C4 120.19(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C8 C7 120.06(17) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?

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 N2 C10 -171.83(16) . . . . ?
Br1 Cu1 N2 C10 28.00(19) . . . . ?
N1 Cu1 N2 C6 22.58(11) . . . . ?
Br1 Cu1 N2 C6 -137.59(9) . . . . ?
N2 Cu1 N1 C1 171.93(16) . . . . ?
Br1 Cu1 N1 C1 -27.89(19) . . . . ?
N2 Cu1 N1 C5 -23.23(11) . . . . ?
Br1 Cu1 N1 C5 136.96(9) . . . . ?
C6 N2 C10 C9 3.1(2) . . . . ?
Cu1 N2 C10 C9 -161.02(13) . . . . ?
C6 N2 C10 C17 -178.88(15) . . . . ?
Cu1 N2 C10 C17 17.0(2) . . . . ?
N2 C10 C9 C8 -0.2(3) . . . . ?
C17 C10 C9 C8 -178.16(17) . . . . ?
N2 C10 C17 C19 159.81(17) . . . . ?
C9 C10 C17 C19 -22.2(2) . . . . ?
N2 C10 C17 C18 39.3(2) . . . . ?
C9 C10 C17 C18 -142.65(17) . . . . ?
N2 C10 C17 C20 -81.0(2) . . . . ?
C9 C10 C17 C20 97.1(2) . . . . ?
C12 C11 C4 C3 -176.39(18) . . . . ?
C12 C11 C4 C5 2.4(3) . . . . ?
C5 N1 C1 C2 -5.4(3) . . . . ?
Cu1 N1 C1 C2 157.89(14) . . . . ?
C5 N1 C1 C13 175.36(15) . . . . ?
Cu1 N1 C1 C13 -21.3(2) . . . . ?
C3 C2 C1 N1 2.0(3) . . . . ?
C3 C2 C1 C13 -178.84(18) . . . . ?
C1 N1 C5 C4 4.6(2) . . . . ?
Cu1 N1 C5 C4 -162.51(13) . . . . ?
C1 N1 C5 C6 -172.53(15) . . . . ?
Cu1 N1 C5 C6 20.40(18) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
C11 C4 C5 N1 -178.99(16) . . . . ?
C3 C4 C5 C6 176.93(16) . . . . ?
C11 C4 C5 C6 -1.9(2) . . . . ?
N1 C1 C13 C16 -34.9(2) . . . . ?
C2 C1 C13 C16 145.86(19) . . . . ?
N1 C1 C13 C14 -154.23(18) . . . . ?
C2 C1 C13 C14 26.6(2) . . . . ?
N1 C1 C13 C15 86.6(2) . . . . ?
C2 C1 C13 C15 -92.6(2) . . . . ?
C10 N2 C6 C7 -3.7(2) . . . . ?
Cu1 N2 C6 C7 164.09(13) . . . . ?
C10 N2 C6 C5 173.84(15) . . . . ?
Cu1 N2 C6 C5 -18.39(17) . . . . ?
N1 C5 C6 N2 -1.3(2) . . . . ?
C4 C5 C6 N2 -178.45(15) . . . . ?
N1 C5 C6 C7 176.33(15) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
N2 C6 C7 C8 1.3(2) . . . . ?
C5 C6 C7 C8 -176.22(16) . . . . ?
N2 C6 C7 C12 -179.30(16) . . . . ?
C5 C6 C7 C12 3.2(2) . . . . ?
C4 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 176.56(17) . . . . ?
C6 C7 C12 C11 -2.8(3) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C5 C4 C3 C2 -3.4(3) . . . . ?
C11 C4 C3 C2 175.46(18) . . . . ?
C10 C9 C8 C7 -2.2(3) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?
C12 C7 C8 C9 -177.74(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.083
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wb3ck
_database_code_depnum_ccdc_archive 'CCDC 1006216'
_audit_update_record             
;
2014-06-02 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Cu2 N4'
_chemical_formula_sum            'C22 H24 Cu2 N4'
_chemical_formula_weight         471.53

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_int_tables_number      14

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                   8.5167(3)
_cell_length_b                   12.2692(3)
_cell_length_c                   20.6552(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.754(3)
_cell_angle_gamma                90.00
_cell_volume                     2150.90(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8720
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.85

_exptl_crystal_description       fragment
_exptl_crystal_colour            'dark orange'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 The collected data cover nominally a full sphere of the reciprocal space.
 A combination of 11 sets of ω scans were used; each set at different \j,
 2θ or κ angles and each scan 1.0 deg in ω.
 Each frame was exposured for 10s. Nominal crystal to detector distance 45 mm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, EOS'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42497
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         29.50
_reflns_number_total             5951
_reflns_number_gt                4858
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    
;
 SHELXS-97 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)
;
_computing_structure_refinement  
;
 SHELXL-97 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)
;
_computing_publication_material  
;
 WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838.)
;


_refine_special_details          
;
 Two sites are occupied by disordered CN groups and were refined using a split atom model;
 a ISOR restrain is applied to the disordered atom pairs.

 All H atoms were refined using a riding model, with a common U restrained
 to be 1.2 (1.5 for methyl groups) times the equivalent isotropic displacement
 parameter of the parent atom. Methyl groups were treated as rigid bodies and
 allowed to rotate about the E-CH3 bond.


 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)+(0.0241P)²+1.1724P] 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         5951
_refine_ls_number_parameters     277
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_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
C1 C 0.0976(2) 0.03666(15) 0.21949(8) 0.0176(4) Uani 1 1 d . . .
C2 C 0.1555(2) 0.02123(16) 0.15794(9) 0.0228(4) Uani 1 1 d . . .
H2 H 0.0992 0.0508 0.1204 0.027 Uiso 1 1 calc R . .
C3 C 0.2915(2) -0.03583(16) 0.15181(9) 0.0228(4) Uani 1 1 d . . .
H3 H 0.3315 -0.0433 0.1105 0.027 Uiso 1 1 calc R . .
C4 C 0.3719(2) -0.08357(16) 0.20715(9) 0.0188(4) Uani 1 1 d . . .
C5 C 0.3097(2) -0.06385(14) 0.26676(8) 0.0151(3) Uani 1 1 d . . .
C6 C 0.3789(2) -0.11667(14) 0.32506(8) 0.0150(3) Uani 1 1 d . . .
C7 C 0.5076(2) -0.18753(15) 0.32096(9) 0.0189(4) Uani 1 1 d . . .
C8 C 0.5621(2) -0.24058(17) 0.37885(10) 0.0244(4) Uani 1 1 d . . .
H8 H 0.6525 -0.2861 0.3797 0.029 Uiso 1 1 calc R . .
C9 C 0.4857(2) -0.22708(16) 0.43400(9) 0.0217(4) Uani 1 1 d . . .
H9 H 0.5209 -0.2655 0.4724 0.026 Uiso 1 1 calc R . .
C10 C 0.3548(2) -0.15648(14) 0.43431(8) 0.0164(3) Uani 1 1 d . . .
C11 C 0.5072(2) -0.15338(17) 0.20484(9) 0.0232(4) Uani 1 1 d . . .
H11 H 0.5521 -0.1646 0.1648 0.028 Uiso 1 1 calc R . .
C12 C 0.5710(2) -0.20330(17) 0.25935(10) 0.0257(4) Uani 1 1 d . . .
H12 H 0.6596 -0.2497 0.2568 0.031 Uiso 1 1 calc R . .
C13 C -0.0559(2) 0.09831(16) 0.22742(9) 0.0215(4) Uani 1 1 d . . .
C14 C -0.1710(3) 0.0852(2) 0.16638(10) 0.0339(5) Uani 1 1 d . . .
H14A H -0.2726 0.1181 0.1742 0.051 Uiso 1 1 calc R . .
H14B H -0.1859 0.0076 0.1566 0.051 Uiso 1 1 calc R . .
H14C H -0.1278 0.1216 0.1295 0.051 Uiso 1 1 calc R . .
C15 C -0.0177(3) 0.21927(17) 0.23831(11) 0.0331(5) Uani 1 1 d . . .
H15A H -0.1150 0.2594 0.2441 0.050 Uiso 1 1 calc R . .
H15B H 0.0310 0.2482 0.2005 0.050 Uiso 1 1 calc R . .
H15C H 0.0554 0.2275 0.2772 0.050 Uiso 1 1 calc R . .
C16 C -0.1381(2) 0.05431(19) 0.28543(10) 0.0281(5) Uani 1 1 d . . .
H16A H -0.0726 0.0692 0.3257 0.042 Uiso 1 1 calc R . .
H16B H -0.1536 -0.0245 0.2806 0.042 Uiso 1 1 calc R . .
H16C H -0.2406 0.0901 0.2870 0.042 Uiso 1 1 calc R . .
C17 C 0.2591(2) -0.14375(15) 0.49353(8) 0.0188(4) Uani 1 1 d . . .
C18 C 0.0829(2) -0.13652(18) 0.47120(9) 0.0252(4) Uani 1 1 d . . .
H18A H 0.0637 -0.0720 0.4437 0.038 Uiso 1 1 calc R . .
H18B H 0.0219 -0.1309 0.5092 0.038 Uiso 1 1 calc R . .
H18C H 0.0508 -0.2020 0.4464 0.038 Uiso 1 1 calc R . .
C19 C 0.3124(3) -0.04042(17) 0.53146(9) 0.0260(4) Uani 1 1 d . . .
H19A H 0.4232 -0.0479 0.5478 0.039 Uiso 1 1 calc R . .
H19B H 0.2476 -0.0306 0.5681 0.039 Uiso 1 1 calc R . .
H19C H 0.3003 0.0230 0.5026 0.039 Uiso 1 1 calc R . .
C20 C 0.2830(3) -0.24283(18) 0.53891(10) 0.0293(5) Uani 1 1 d . . .
H20A H 0.2581 -0.3097 0.5143 0.044 Uiso 1 1 calc R . .
H20B H 0.2133 -0.2366 0.5742 0.044 Uiso 1 1 calc R . .
H20C H 0.3929 -0.2453 0.5572 0.044 Uiso 1 1 calc R . .
C21 C 0.2078(2) 0.18434(15) 0.40423(8) 0.0165(3) Uani 1 1 d . . .
N1 N 0.17786(16) -0.00229(12) 0.27280(7) 0.0146(3) Uani 1 1 d . . .
N2 N 0.30859(16) -0.09913(12) 0.38109(7) 0.0139(3) Uani 1 1 d . . .
N3 N 0.22502(18) 0.27116(14) 0.42456(7) 0.0208(3) Uani 1 1 d . . .
Cu1 Cu 0.19468(3) 0.045578(18) 0.368430(10) 0.01538(6) Uani 1 1 d . . .
Cu2 Cu 0.24363(3) 0.410798(19) 0.467085(11) 0.02143(7) Uani 1 1 d . . .
C22 C 0.454(4) 0.482(3) 0.4953(12) 0.015(3) Uani 0.50 1 d PU . .
N4 N 0.433(3) 0.474(2) 0.4868(10) 0.014(3) Uani 0.50 1 d PU . .
C23 C 0.042(3) 0.486(2) 0.4930(16) 0.015(3) Uani 0.50 1 d PU . .
N5 N 0.067(3) 0.4716(18) 0.4916(14) 0.016(3) Uani 0.50 1 d PU . .


_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
C1 N1 1.335(2) . ?
C1 C2 1.414(3) . ?
C1 C13 1.531(3) . ?
C2 C3 1.368(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(2) . ?
C4 C11 1.439(3) . ?
C5 N1 1.368(2) . ?
C5 C6 1.449(2) . ?
C6 N2 1.364(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.406(3) . ?
C7 C12 1.436(3) . ?
C8 C9 1.368(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(2) . ?
C9 H9 0.9500 . ?
C10 N2 1.337(2) . ?
C10 C17 1.533(3) . ?
C11 C12 1.355(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.532(3) . ?
C13 C16 1.535(3) . ?
C13 C14 1.540(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.536(3) . ?
C17 C20 1.538(3) . ?
C17 C19 1.539(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N3 1.150(2) . ?
C21 Cu1 1.8558(19) . ?
N1 Cu1 2.0542(14) . ?
N2 Cu1 2.0297(14) . ?
N3 Cu2 1.9258(16) . ?
Cu2 N5 1.79(2) . ?
Cu2 N4 1.80(2) . ?
Cu2 C22 2.03(3) . ?
Cu2 C23 2.05(3) . ?
C22 C22 0.91(6) 3_666 ?
C22 N4 1.140(9) 3_666 ?
N4 C22 1.140(9) 3_666 ?
N4 N4 1.38(5) 3_666 ?
C23 C23 0.88(6) 3_566 ?
C23 N5 1.136(9) 3_566 ?
N5 C23 1.136(9) 3_566 ?
N5 N5 1.40(4) 3_566 ?

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 C1 C2 120.07(17) . . ?
N1 C1 C13 118.14(16) . . ?
C2 C1 C13 121.79(16) . . ?
C3 C2 C1 120.84(17) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.71(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 116.53(17) . . ?
C5 C4 C11 119.59(17) . . ?
C3 C4 C11 123.82(17) . . ?
N1 C5 C4 123.28(16) . . ?
N1 C5 C6 116.84(15) . . ?
C4 C5 C6 119.71(16) . . ?
N2 C6 C7 123.20(16) . . ?
N2 C6 C5 117.25(15) . . ?
C7 C6 C5 119.44(16) . . ?
C8 C7 C6 116.03(16) . . ?
C8 C7 C12 124.70(17) . . ?
C6 C7 C12 119.26(17) . . ?
C9 C8 C7 120.38(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.55(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C10 C9 119.87(16) . . ?
N2 C10 C17 117.57(15) . . ?
C9 C10 C17 122.55(16) . . ?
C12 C11 C4 120.55(17) . . ?
C12 C11 H11 119.7 . . ?
C4 C11 H11 119.7 . . ?
C11 C12 C7 121.38(18) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C1 C13 C15 108.75(16) . . ?
C1 C13 C16 111.02(16) . . ?
C15 C13 C16 109.34(17) . . ?
C1 C13 C14 110.61(16) . . ?
C15 C13 C14 109.53(17) . . ?
C16 C13 C14 107.56(17) . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 C18 109.69(14) . . ?
C10 C17 C20 110.70(16) . . ?
C18 C17 C20 107.78(16) . . ?
C10 C17 C19 109.66(15) . . ?
C18 C17 C19 110.17(17) . . ?
C20 C17 C19 108.81(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 Cu1 175.53(16) . . ?
C1 N1 C5 119.36(15) . . ?
C1 N1 Cu1 132.90(13) . . ?
C5 N1 Cu1 104.67(11) . . ?
C10 N2 C6 119.66(15) . . ?
C10 N2 Cu1 132.18(12) . . ?
C6 N2 Cu1 105.51(11) . . ?
C21 N3 Cu2 173.64(15) . . ?
C21 Cu1 N2 137.63(7) . . ?
C21 Cu1 N1 129.98(7) . . ?
N2 Cu1 N1 82.43(6) . . ?
N5 Cu2 N4 120.9(11) . . ?
N5 Cu2 N3 117.4(7) . . ?
N4 Cu2 N3 121.6(8) . . ?
N5 Cu2 C22 118.7(11) . . ?
N4 Cu2 C22 3.6(15) . . ?
N3 Cu2 C22 123.5(9) . . ?
N5 Cu2 C23 2.2(16) . . ?
N4 Cu2 C23 119.8(11) . . ?
N3 Cu2 C23 118.5(8) . . ?
C22 Cu2 C23 117.8(11) . . ?
C22 C22 N4 6(3) 3_666 3_666 ?
C22 C22 Cu2 175(5) 3_666 . ?
N4 C22 Cu2 176.3(11) 3_666 . ?
C22 N4 N4 4(2) 3_666 3_666 ?
C22 N4 Cu2 173.2(5) 3_666 . ?
N4 N4 Cu2 169(3) 3_666 . ?
C23 C23 N5 5(4) 3_566 3_566 ?
C23 C23 Cu2 175(5) 3_566 . ?
N5 C23 Cu2 178.3(12) 3_566 . ?
C23 N5 N5 3(2) 3_566 3_566 ?
C23 N5 Cu2 177.1(6) 3_566 . ?
N5 N5 Cu2 175(3) 3_566 . ?

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 C1 C2 C3 1.7(3) . . . . ?
C13 C1 C2 C3 -178.81(18) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C2 C3 C4 C5 -3.3(3) . . . . ?
C2 C3 C4 C11 173.99(18) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C11 C4 C5 N1 -177.22(17) . . . . ?
C3 C4 C5 C6 175.45(16) . . . . ?
C11 C4 C5 C6 -2.0(3) . . . . ?
N1 C5 C6 N2 -1.1(2) . . . . ?
C4 C5 C6 N2 -176.61(16) . . . . ?
N1 C5 C6 C7 175.30(16) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
N2 C6 C7 C8 -0.2(3) . . . . ?
C5 C6 C7 C8 -176.35(17) . . . . ?
N2 C6 C7 C12 178.17(17) . . . . ?
C5 C6 C7 C12 2.0(3) . . . . ?
C6 C7 C8 C9 3.7(3) . . . . ?
C12 C7 C8 C9 -174.55(19) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 N2 -2.5(3) . . . . ?
C8 C9 C10 C17 176.23(18) . . . . ?
C5 C4 C11 C12 2.5(3) . . . . ?
C3 C4 C11 C12 -174.77(19) . . . . ?
C4 C11 C12 C7 -0.7(3) . . . . ?
C8 C7 C12 C11 176.63(19) . . . . ?
C6 C7 C12 C11 -1.6(3) . . . . ?
N1 C1 C13 C15 89.0(2) . . . . ?
C2 C1 C13 C15 -90.5(2) . . . . ?
N1 C1 C13 C16 -31.3(2) . . . . ?
C2 C1 C13 C16 149.18(18) . . . . ?
N1 C1 C13 C14 -150.62(18) . . . . ?
C2 C1 C13 C14 29.8(3) . . . . ?
N2 C10 C17 C18 39.1(2) . . . . ?
C9 C10 C17 C18 -139.65(18) . . . . ?
N2 C10 C17 C20 157.95(16) . . . . ?
C9 C10 C17 C20 -20.8(2) . . . . ?
N2 C10 C17 C19 -82.0(2) . . . . ?
C9 C10 C17 C19 99.2(2) . . . . ?
C2 C1 N1 C5 -4.8(3) . . . . ?
C13 C1 N1 C5 175.69(16) . . . . ?
C2 C1 N1 Cu1 152.08(14) . . . . ?
C13 C1 N1 Cu1 -27.5(2) . . . . ?
C4 C5 N1 C1 3.9(3) . . . . ?
C6 C5 N1 C1 -171.46(16) . . . . ?
C4 C5 N1 Cu1 -158.79(15) . . . . ?
C6 C5 N1 Cu1 25.86(18) . . . . ?
C9 C10 N2 C6 6.0(2) . . . . ?
C17 C10 N2 C6 -172.80(15) . . . . ?
C9 C10 N2 Cu1 -152.63(14) . . . . ?
C17 C10 N2 Cu1 28.6(2) . . . . ?
C7 C6 N2 C10 -4.7(3) . . . . ?
C5 C6 N2 C10 171.50(16) . . . . ?
C7 C6 N2 Cu1 159.00(15) . . . . ?
C5 C6 N2 Cu1 -24.76(18) . . . . ?
Cu1 C21 N3 Cu2 -144.1(14) . . . . ?
N3 C21 Cu1 N2 69(2) . . . . ?
N3 C21 Cu1 N1 -62(2) . . . . ?
C10 N2 Cu1 C21 46.3(2) . . . . ?
C6 N2 Cu1 C21 -114.49(13) . . . . ?
C10 N2 Cu1 N1 -168.96(17) . . . . ?
C6 N2 Cu1 N1 30.21(11) . . . . ?
C1 N1 Cu1 C21 -40.4(2) . . . . ?
C5 N1 Cu1 C21 118.83(12) . . . . ?
C1 N1 Cu1 N2 170.13(17) . . . . ?
C5 N1 Cu1 N2 -30.62(11) . . . . ?
C21 N3 Cu2 N5 -57.4(17) . . . . ?
C21 N3 Cu2 N4 118.3(16) . . . . ?
C21 N3 Cu2 C22 114.6(17) . . . . ?
C21 N3 Cu2 C23 -59.6(17) . . . . ?
N5 Cu2 C22 C22 -87(54) . . . 3_666 ?
N4 Cu2 C22 C22 40(37) . . . 3_666 ?
N3 Cu2 C22 C22 101(54) . . . 3_666 ?
C23 Cu2 C22 C22 -85(54) . . . 3_666 ?
N5 Cu2 C22 N4 9(22) . . . 3_666 ?
N4 Cu2 C22 N4 137(45) . . . 3_666 ?
N3 Cu2 C22 N4 -163(21) . . . 3_666 ?
C23 Cu2 C22 N4 12(22) . . . 3_666 ?
N5 Cu2 N4 C22 32(5) . . . 3_666 ?
N3 Cu2 N4 C22 -143(4) . . . 3_666 ?
C22 Cu2 N4 C22 -22(24) . . . 3_666 ?
C23 Cu2 N4 C22 34(5) . . . 3_666 ?
N5 Cu2 N4 N4 43(16) . . . 3_666 ?
N3 Cu2 N4 N4 -133(15) . . . 3_666 ?
C22 Cu2 N4 N4 -11(12) . . . 3_666 ?
C23 Cu2 N4 N4 45(16) . . . 3_666 ?
N5 Cu2 C23 C23 27(24) . . . 3_566 ?
N4 Cu2 C23 C23 -92(53) . . . 3_566 ?
N3 Cu2 C23 C23 85(53) . . . 3_566 ?
C22 Cu2 C23 C23 -89(53) . . . 3_566 ?
N5 Cu2 C23 N5 95(71) . . . 3_566 ?
N4 Cu2 C23 N5 -24(42) . . . 3_566 ?
N3 Cu2 C23 N5 154(42) . . . 3_566 ?
C22 Cu2 C23 N5 -21(42) . . . 3_566 ?
N4 Cu2 N5 C23 27(13) . . . 3_566 ?
N3 Cu2 N5 C23 -158(13) . . . 3_566 ?
C22 Cu2 N5 C23 30(13) . . . 3_566 ?
C23 Cu2 N5 C23 -35(35) . . . 3_566 ?
N4 Cu2 N5 N5 47(33) . . . 3_566 ?
N3 Cu2 N5 N5 -137(32) . . . 3_566 ?
C22 Cu2 N5 N5 51(33) . . . 3_566 ?
C23 Cu2 N5 N5 -15(14) . . . 3_566 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.073
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fro5846
_database_code_depnum_ccdc_archive 'CCDC 1006445'
_audit_update_record             
;
2014-06-03 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Cu I N2'
_chemical_formula_weight         482.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca21

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

_cell_length_a                   20.4147(4)
_cell_length_b                   9.7229(2)
_cell_length_c                   19.5841(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3887.25(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7592
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      27.88

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    2.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5740
_exptl_absorpt_correction_T_max  0.8762
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16417
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6417
_reflns_number_gt                5971
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0425P)²+26.8636P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.51(4)
_refine_ls_number_reflns         6417
_refine_ls_number_parameters     446
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Cu1A Cu 0.94629(6) 0.54047(12) -0.27302(6) 0.0362(3) Uani 1 1 d . . .
I1A I 1.04284(3) 0.48670(8) -0.34174(3) 0.0537(2) Uani 1 1 d . . .
C1A C 0.8300(4) 0.4454(8) -0.2143(5) 0.0324(19) Uani 1 1 d . . .
N2A N 0.8473(4) 0.4983(8) -0.2777(4) 0.0346(18) Uani 1 1 d . . .
C3A C 0.8064(4) 0.4787(9) -0.3300(5) 0.036(2) Uani 1 1 d . . .
C4A C 0.7497(5) 0.3964(12) -0.3215(5) 0.050(3) Uani 1 1 d . . .
H4A H 0.7220 0.3814 -0.3592 0.061 Uiso 1 1 calc R . .
C5A C 0.7342(5) 0.3383(10) -0.2603(7) 0.051(3) Uani 1 1 d . . .
H5A H 0.6978 0.2796 -0.2567 0.061 Uiso 1 1 calc R . .
C6A C 0.7731(5) 0.3668(10) -0.2021(5) 0.038(2) Uani 1 1 d . . .
C7A C 0.7587(5) 0.3167(10) -0.1361(6) 0.047(2) Uani 1 1 d . . .
H7A H 0.7217 0.2610 -0.1290 0.057 Uiso 1 1 calc R . .
C8A C 0.7982(5) 0.3491(11) -0.0833(5) 0.046(2) Uani 1 1 d . . .
H8A H 0.7883 0.3145 -0.0396 0.055 Uiso 1 1 calc R . .
C9A C 0.8544(5) 0.4341(9) -0.0916(5) 0.038(2) Uani 1 1 d . . .
C10A C 0.8957(5) 0.4780(11) -0.0377(5) 0.044(2) Uani 1 1 d . . .
H10A H 0.8866 0.4487 0.0071 0.053 Uiso 1 1 calc R . .
C11A C 0.9465(5) 0.5591(10) -0.0488(6) 0.046(2) Uani 1 1 d . . .
H11A H 0.9727 0.5876 -0.0119 0.055 Uiso 1 1 calc R . .
C12A C 0.9623(5) 0.6043(11) -0.1175(5) 0.040(2) Uani 1 1 d . . .
N13A N 0.9251(4) 0.5600(7) -0.1693(4) 0.0323(16) Uani 1 1 d . . .
C14A C 0.8722(5) 0.4792(9) -0.1571(5) 0.034(2) Uani 1 1 d . . .
C15A C 0.8209(6) 0.5484(12) -0.3978(6) 0.048(3) Uani 1 1 d . . .
C16A C 0.7577(7) 0.5875(19) -0.4341(7) 0.091(5) Uani 1 1 d . . .
H16A H 0.7384 0.5061 -0.4545 0.136 Uiso 1 1 calc R . .
H16B H 0.7671 0.6544 -0.4695 0.136 Uiso 1 1 calc R . .
H16C H 0.7273 0.6269 -0.4015 0.136 Uiso 1 1 calc R . .
C17A C 0.8611(8) 0.4499(15) -0.4421(6) 0.078(4) Uani 1 1 d . . .
H17A H 0.9010 0.4249 -0.4183 0.117 Uiso 1 1 calc R . .
H17B H 0.8721 0.4947 -0.4849 0.117 Uiso 1 1 calc R . .
H17C H 0.8357 0.3678 -0.4514 0.117 Uiso 1 1 calc R . .
C18A C 0.8614(6) 0.6798(12) -0.3866(6) 0.054(3) Uani 1 1 d . . .
H18A H 0.8403 0.7367 -0.3524 0.082 Uiso 1 1 calc R . .
H18B H 0.8644 0.7304 -0.4292 0.082 Uiso 1 1 calc R . .
H18C H 0.9050 0.6553 -0.3712 0.082 Uiso 1 1 calc R . .
C19A C 1.0196(5) 0.6972(11) -0.1305(5) 0.047(2) Uani 1 1 d . . .
C20A C 1.0047(7) 0.7934(13) -0.1915(6) 0.062(3) Uani 1 1 d . . .
H20A H 1.0034 0.7400 -0.2333 0.093 Uiso 1 1 calc R . .
H20B H 1.0386 0.8629 -0.1950 0.093 Uiso 1 1 calc R . .
H20C H 0.9626 0.8377 -0.1845 0.093 Uiso 1 1 calc R . .
C21A C 1.0792(5) 0.6067(14) -0.1440(8) 0.071(4) Uani 1 1 d . . .
H21A H 1.0850 0.5432 -0.1063 0.107 Uiso 1 1 calc R . .
H21B H 1.1179 0.6640 -0.1484 0.107 Uiso 1 1 calc R . .
H21C H 1.0726 0.5554 -0.1859 0.107 Uiso 1 1 calc R . .
C22A C 1.0320(7) 0.7942(13) -0.0675(6) 0.067(4) Uani 1 1 d . . .
H22A H 0.9929 0.8480 -0.0585 0.100 Uiso 1 1 calc R . .
H22B H 1.0683 0.8554 -0.0774 0.100 Uiso 1 1 calc R . .
H22C H 1.0424 0.7389 -0.0277 0.100 Uiso 1 1 calc R . .
Cu1B Cu 0.80071(6) 0.00485(14) -0.04369(6) 0.0425(3) Uani 1 1 d . . .
I1B I 0.70211(3) 0.04365(8) 0.02464(3) 0.04984(19) Uani 1 1 d . . .
C1B C 0.8744(4) 0.0613(9) -0.1593(5) 0.034(2) Uani 1 1 d . . .
N2B N 0.8204(4) -0.0165(9) -0.1474(4) 0.0386(18) Uani 1 1 d . . .
C3B C 0.7841(5) -0.0577(11) -0.1994(5) 0.039(2) Uani 1 1 d . . .
C4B C 0.7978(5) -0.0158(12) -0.2668(5) 0.050(3) Uani 1 1 d . . .
H4B H 0.7703 -0.0439 -0.3027 0.060 Uiso 1 1 calc R . .
C5B C 0.8511(6) 0.0660(12) -0.2803(6) 0.052(3) Uani 1 1 d . . .
H5B H 0.8599 0.0953 -0.3252 0.063 Uiso 1 1 calc R . .
C6B C 0.8920(5) 0.1049(11) -0.2267(5) 0.047(2) Uani 1 1 d . . .
C7B C 0.9490(5) 0.1901(11) -0.2356(6) 0.052(3) Uani 1 1 d . . .
H7B H 0.9590 0.2232 -0.2795 0.062 Uiso 1 1 calc R . .
C8B C 0.9879(5) 0.2233(11) -0.1838(6) 0.050(3) Uani 1 1 d . . .
H8B H 1.0259 0.2755 -0.1917 0.060 Uiso 1 1 calc R . .
C9B C 0.9720(5) 0.1793(11) -0.1151(5) 0.044(2) Uani 1 1 d . . .
C10B C 1.0126(5) 0.2068(13) -0.0592(7) 0.059(3) Uani 1 1 d . . .
H10B H 1.0512 0.2582 -0.0654 0.071 Uiso 1 1 calc R . .
C11B C 0.9967(6) 0.1595(14) 0.0039(6) 0.065(3) Uani 1 1 d . . .
H11B H 1.0243 0.1781 0.0412 0.078 Uiso 1 1 calc R . .
C12B C 0.9395(5) 0.0835(13) 0.0136(6) 0.054(3) Uani 1 1 d . . .
N13B N 0.8991(4) 0.0564(9) -0.0401(4) 0.042(2) Uani 1 1 d . . .
C14B C 0.9159(5) 0.0991(11) -0.1035(5) 0.043(2) Uani 1 1 d . . .
C15B C 0.7249(5) -0.1537(11) -0.1848(5) 0.045(2) Uani 1 1 d . . .
C16B C 0.7097(6) -0.2441(13) -0.2477(6) 0.063(3) Uani 1 1 d . . .
H16D H 0.6951 -0.1862 -0.2851 0.094 Uiso 1 1 calc R . .
H16E H 0.6755 -0.3093 -0.2362 0.094 Uiso 1 1 calc R . .
H16F H 0.7489 -0.2934 -0.2612 0.094 Uiso 1 1 calc R . .
C17B C 0.6654(5) -0.0552(13) -0.1706(7) 0.056(3) Uani 1 1 d . . .
H17D H 0.6746 0.0002 -0.1305 0.084 Uiso 1 1 calc R . .
H17E H 0.6263 -0.1095 -0.1628 0.084 Uiso 1 1 calc R . .
H17F H 0.6587 0.0044 -0.2097 0.084 Uiso 1 1 calc R . .
C18B C 0.7369(6) -0.2486(11) -0.1243(6) 0.059(3) Uani 1 1 d . . .
H18D H 0.7767 -0.3011 -0.1319 0.088 Uiso 1 1 calc R . .
H18E H 0.7002 -0.3110 -0.1192 0.088 Uiso 1 1 calc R . .
H18F H 0.7416 -0.1941 -0.0830 0.088 Uiso 1 1 calc R . .
C19B C 0.9204(6) 0.0260(12) 0.0831(6) 0.049(3) Uani 1 1 d . . .
C20B C 0.8911(7) -0.1169(14) 0.0771(6) 0.069(4) Uani 1 1 d . . .
H20D H 0.8482 -0.1107 0.0560 0.104 Uiso 1 1 calc R . .
H20E H 0.8869 -0.1571 0.1222 0.104 Uiso 1 1 calc R . .
H20F H 0.9194 -0.1740 0.0492 0.104 Uiso 1 1 calc R . .
C21B C 0.8727(7) 0.1227(14) 0.1167(7) 0.071(4) Uani 1 1 d . . .
H21D H 0.8918 0.2138 0.1195 0.107 Uiso 1 1 calc R . .
H21E H 0.8627 0.0898 0.1624 0.107 Uiso 1 1 calc R . .
H21F H 0.8327 0.1266 0.0900 0.107 Uiso 1 1 calc R . .
C22B C 0.9824(8) 0.012(2) 0.1284(7) 0.100(6) Uani 1 1 d . . .
H22D H 1.0112 -0.0576 0.1090 0.150 Uiso 1 1 calc R . .
H22E H 0.9697 -0.0156 0.1741 0.150 Uiso 1 1 calc R . .
H22F H 1.0052 0.0991 0.1302 0.150 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
Cu1A N2A 2.064(8) . ?
Cu1A N13A 2.086(8) . ?
Cu1A I1A 2.4432(13) . ?
C1A N2A 1.391(12) . ?
C1A C6A 1.410(13) . ?
C1A C14A 1.452(13) . ?
N2A C3A 1.334(12) . ?
C3A C4A 1.417(14) . ?
C3A C15A 1.520(14) . ?
C4A C5A 1.362(16) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.416(14) . ?
C5A H5A 0.9400 . ?
C6A C7A 1.413(15) . ?
C7A C8A 1.349(15) . ?
C7A H7A 0.9400 . ?
C8A C9A 1.424(13) . ?
C8A H8A 0.9400 . ?
C9A C14A 1.402(13) . ?
C9A C10A 1.417(14) . ?
C10A C11A 1.322(15) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.452(15) . ?
C11A H11A 0.9400 . ?
C12A N13A 1.338(12) . ?
C12A C19A 1.501(13) . ?
N13A C14A 1.356(12) . ?
C15A C16A 1.522(17) . ?
C15A C17A 1.532(16) . ?
C15A C18A 1.538(16) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16A H16C 0.9700 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A H17C 0.9700 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A H18C 0.9700 . ?
C19A C21A 1.524(15) . ?
C19A C20A 1.548(15) . ?
C19A C22A 1.573(14) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20A H20C 0.9700 . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C21A H21C 0.9700 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C22A H22C 0.9700 . ?
Cu1B N13B 2.072(9) . ?
Cu1B N2B 2.081(8) . ?
Cu1B I1B 2.4463(13) . ?
C1B N2B 1.356(12) . ?
C1B C14B 1.430(13) . ?
C1B C6B 1.432(13) . ?
N2B C3B 1.323(13) . ?
C3B C4B 1.409(14) . ?
C3B C15B 1.554(15) . ?
C4B C5B 1.373(16) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.395(15) . ?
C5B H5B 0.9400 . ?
C6B C7B 1.438(15) . ?
C7B C8B 1.329(16) . ?
C7B H7B 0.9400 . ?
C8B C9B 1.448(14) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.399(15) . ?
C9B C14B 1.404(14) . ?
C10B C11B 1.359(17) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.395(17) . ?
C11B H11B 0.9400 . ?
C12B N13B 1.362(14) . ?
C12B C19B 1.523(17) . ?
N13B C14B 1.352(13) . ?
C15B C18B 1.523(15) . ?
C15B C16B 1.543(14) . ?
C15B C17B 1.572(14) . ?
C16B H16D 0.9700 . ?
C16B H16E 0.9700 . ?
C16B H16F 0.9700 . ?
C17B H17D 0.9700 . ?
C17B H17E 0.9700 . ?
C17B H17F 0.9700 . ?
C18B H18D 0.9700 . ?
C18B H18E 0.9700 . ?
C18B H18F 0.9700 . ?
C19B C21B 1.505(17) . ?
C19B C20B 1.518(18) . ?
C19B C22B 1.552(17) . ?
C20B H20D 0.9700 . ?
C20B H20E 0.9700 . ?
C20B H20F 0.9700 . ?
C21B H21D 0.9700 . ?
C21B H21E 0.9700 . ?
C21B H21F 0.9700 . ?
C22B H22D 0.9700 . ?
C22B H22E 0.9700 . ?
C22B H22F 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2A Cu1A N13A 81.9(3) . . ?
N2A Cu1A I1A 136.3(2) . . ?
N13A Cu1A I1A 136.3(2) . . ?
N2A C1A C6A 124.1(9) . . ?
N2A C1A C14A 117.1(8) . . ?
C6A C1A C14A 118.8(8) . . ?
C3A N2A C1A 118.2(8) . . ?
C3A N2A Cu1A 132.5(6) . . ?
C1A N2A Cu1A 106.4(6) . . ?
N2A C3A C4A 120.2(9) . . ?
N2A C3A C15A 119.0(8) . . ?
C4A C3A C15A 120.8(9) . . ?
C5A C4A C3A 121.8(9) . . ?
C5A C4A H4A 119.1 . . ?
C3A C4A H4A 119.1 . . ?
C4A C5A C6A 119.8(9) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A C7A 120.8(9) . . ?
C1A C6A C5A 115.6(9) . . ?
C7A C6A C5A 123.6(9) . . ?
C8A C7A C6A 119.9(9) . . ?
C8A C7A H7A 120.1 . . ?
C6A C7A H7A 120.1 . . ?
C7A C8A C9A 121.9(9) . . ?
C7A C8A H8A 119.0 . . ?
C9A C8A H8A 119.0 . . ?
C14A C9A C10A 115.6(8) . . ?
C14A C9A C8A 119.7(9) . . ?
C10A C9A C8A 124.6(9) . . ?
C11A C10A C9A 121.6(10) . . ?
C11A C10A H10A 119.2 . . ?
C9A C10A H10A 119.2 . . ?
C10A C11A C12A 120.5(10) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A H11A 119.8 . . ?
N13A C12A C11A 118.6(9) . . ?
N13A C12A C19A 120.6(8) . . ?
C11A C12A C19A 120.8(9) . . ?
C12A N13A C14A 120.3(8) . . ?
C12A N13A Cu1A 130.5(6) . . ?
C14A N13A Cu1A 106.5(6) . . ?
N13A C14A C9A 123.3(9) . . ?
N13A C14A C1A 117.9(8) . . ?
C9A C14A C1A 118.7(8) . . ?
C3A C15A C16A 110.8(10) . . ?
C3A C15A C17A 108.8(10) . . ?
C16A C15A C17A 110.2(12) . . ?
C3A C15A C18A 110.6(9) . . ?
C16A C15A C18A 108.3(11) . . ?
C17A C15A C18A 108.2(10) . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15A C17A H17A 109.5 . . ?
C15A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C15A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C15A C18A H18A 109.5 . . ?
C15A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C15A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C12A C19A C21A 107.7(9) . . ?
C12A C19A C20A 109.9(8) . . ?
C21A C19A C20A 111.9(10) . . ?
C12A C19A C22A 110.7(8) . . ?
C21A C19A C22A 110.7(10) . . ?
C20A C19A C22A 106.0(9) . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C19A C22A H22A 109.5 . . ?
C19A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C19A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
N13B Cu1B N2B 82.5(3) . . ?
N13B Cu1B I1B 137.9(2) . . ?
N2B Cu1B I1B 135.1(2) . . ?
N2B C1B C14B 119.6(9) . . ?
N2B C1B C6B 121.8(9) . . ?
C14B C1B C6B 118.6(9) . . ?
C3B N2B C1B 119.5(8) . . ?
C3B N2B Cu1B 132.4(6) . . ?
C1B N2B Cu1B 105.6(6) . . ?
N2B C3B C4B 121.5(10) . . ?
N2B C3B C15B 118.5(8) . . ?
C4B C3B C15B 120.0(9) . . ?
C5B C4B C3B 120.3(10) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4B C5B C6B 119.1(10) . . ?
C4B C5B H5B 120.5 . . ?
C6B C5B H5B 120.5 . . ?
C5B C6B C1B 117.6(10) . . ?
C5B C6B C7B 123.3(10) . . ?
C1B C6B C7B 119.1(10) . . ?
C8B C7B C6B 122.0(10) . . ?
C8B C7B H7B 119.0 . . ?
C6B C7B H7B 119.0 . . ?
C7B C8B C9B 120.2(10) . . ?
C7B C8B H8B 119.9 . . ?
C9B C8B H8B 119.9 . . ?
C10B C9B C14B 117.6(10) . . ?
C10B C9B C8B 122.4(10) . . ?
C14B C9B C8B 119.8(10) . . ?
C11B C10B C9B 120.3(11) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C10B C11B C12B 120.2(11) . . ?
C10B C11B H11B 119.9 . . ?
C12B C11B H11B 119.9 . . ?
N13B C12B C11B 120.3(11) . . ?
N13B C12B C19B 117.7(10) . . ?
C11B C12B C19B 122.0(10) . . ?
C14B N13B C12B 119.7(9) . . ?
C14B N13B Cu1B 106.8(6) . . ?
C12B N13B Cu1B 131.2(7) . . ?
N13B C14B C9B 121.7(9) . . ?
N13B C14B C1B 118.2(9) . . ?
C9B C14B C1B 120.1(9) . . ?
C18B C15B C16B 108.0(9) . . ?
C18B C15B C3B 112.4(8) . . ?
C16B C15B C3B 110.6(9) . . ?
C18B C15B C17B 110.8(9) . . ?
C16B C15B C17B 109.4(9) . . ?
C3B C15B C17B 105.5(8) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C15B C17B H17D 109.5 . . ?
C15B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C15B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C15B C18B H18D 109.5 . . ?
C15B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C15B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C21B C19B C20B 110.5(11) . . ?
C21B C19B C12B 109.1(10) . . ?
C20B C19B C12B 111.6(10) . . ?
C21B C19B C22B 109.6(11) . . ?
C20B C19B C22B 106.5(11) . . ?
C12B C19B C22B 109.6(10) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19B C21B H21D 109.5 . . ?
C19B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C19B C22B H22D 109.5 . . ?
C19B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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
C6A C1A N2A C3A 2.9(13) . . . . ?
C14A C1A N2A C3A -174.4(8) . . . . ?
C6A C1A N2A Cu1A -160.3(7) . . . . ?
C14A C1A N2A Cu1A 22.4(9) . . . . ?
N13A Cu1A N2A C3A 173.6(9) . . . . ?
I1A Cu1A N2A C3A -31.2(10) . . . . ?
N13A Cu1A N2A C1A -26.5(6) . . . . ?
I1A Cu1A N2A C1A 128.7(5) . . . . ?
C1A N2A C3A C4A -5.1(13) . . . . ?
Cu1A N2A C3A C4A 152.9(8) . . . . ?
C1A N2A C3A C15A 173.6(8) . . . . ?
Cu1A N2A C3A C15A -28.5(13) . . . . ?
N2A C3A C4A C5A 1.8(16) . . . . ?
C15A C3A C4A C5A -176.8(10) . . . . ?
C3A C4A C5A C6A 3.9(16) . . . . ?
N2A C1A C6A C7A -179.9(9) . . . . ?
C14A C1A C6A C7A -2.7(13) . . . . ?
N2A C1A C6A C5A 2.5(14) . . . . ?
C14A C1A C6A C5A 179.8(8) . . . . ?
C4A C5A C6A C1A -5.8(14) . . . . ?
C4A C5A C6A C7A 176.7(10) . . . . ?
C1A C6A C7A C8A 2.9(15) . . . . ?
C5A C6A C7A C8A -179.8(10) . . . . ?
C6A C7A C8A C9A 0.5(15) . . . . ?
C7A C8A C9A C14A -4.1(15) . . . . ?
C7A C8A C9A C10A 176.3(10) . . . . ?
C14A C9A C10A C11A 1.7(15) . . . . ?
C8A C9A C10A C11A -178.8(10) . . . . ?
C9A C10A C11A C12A -0.9(17) . . . . ?
C10A C11A C12A N13A -1.3(16) . . . . ?
C10A C11A C12A C19A 179.5(10) . . . . ?
C11A C12A N13A C14A 2.7(14) . . . . ?
C19A C12A N13A C14A -178.1(9) . . . . ?
C11A C12A N13A Cu1A -156.0(7) . . . . ?
C19A C12A N13A Cu1A 23.1(14) . . . . ?
N2A Cu1A N13A C12A -172.1(9) . . . . ?
I1A Cu1A N13A C12A 32.7(10) . . . . ?
N2A Cu1A N13A C14A 26.9(6) . . . . ?
I1A Cu1A N13A C14A -128.2(5) . . . . ?
C12A N13A C14A C9A -1.9(14) . . . . ?
Cu1A N13A C14A C9A 161.3(7) . . . . ?
C12A N13A C14A C1A 174.1(8) . . . . ?
Cu1A N13A C14A C1A -22.7(9) . . . . ?
C10A C9A C14A N13A -0.3(14) . . . . ?
C8A C9A C14A N13A -179.8(9) . . . . ?
C10A C9A C14A C1A -176.2(8) . . . . ?
C8A C9A C14A C1A 4.2(13) . . . . ?
N2A C1A C14A N13A 0.3(12) . . . . ?
C6A C1A C14A N13A -177.1(8) . . . . ?
N2A C1A C14A C9A 176.5(8) . . . . ?
C6A C1A C14A C9A -0.9(13) . . . . ?
N2A C3A C15A C16A -146.4(11) . . . . ?
C4A C3A C15A C16A 32.2(14) . . . . ?
N2A C3A C15A C17A 92.3(12) . . . . ?
C4A C3A C15A C17A -89.1(12) . . . . ?
N2A C3A C15A C18A -26.3(13) . . . . ?
C4A C3A C15A C18A 152.3(10) . . . . ?
N13A C12A C19A C21A -88.7(12) . . . . ?
C11A C12A C19A C21A 90.5(12) . . . . ?
N13A C12A C19A C20A 33.4(13) . . . . ?
C11A C12A C19A C20A -147.4(10) . . . . ?
N13A C12A C19A C22A 150.1(10) . . . . ?
C11A C12A C19A C22A -30.7(14) . . . . ?
C14B C1B N2B C3B -176.3(9) . . . . ?
C6B C1B N2B C3B 2.4(14) . . . . ?
C14B C1B N2B Cu1B 19.7(10) . . . . ?
C6B C1B N2B Cu1B -161.6(7) . . . . ?
N13B Cu1B N2B C3B 176.2(10) . . . . ?
I1B Cu1B N2B C3B -25.6(11) . . . . ?
N13B Cu1B N2B C1B -22.6(6) . . . . ?
I1B Cu1B N2B C1B 135.6(5) . . . . ?
C1B N2B C3B C4B -4.0(15) . . . . ?
Cu1B N2B C3B C4B 155.1(8) . . . . ?
C1B N2B C3B C15B 176.5(8) . . . . ?
Cu1B N2B C3B C15B -24.4(14) . . . . ?
N2B C3B C4B C5B 2.3(17) . . . . ?
C15B C3B C4B C5B -178.2(10) . . . . ?
C3B C4B C5B C6B 1.0(17) . . . . ?
C4B C5B C6B C1B -2.5(15) . . . . ?
C4B C5B C6B C7B 179.9(10) . . . . ?
N2B C1B C6B C5B 0.8(14) . . . . ?
C14B C1B C6B C5B 179.5(9) . . . . ?
N2B C1B C6B C7B 178.5(9) . . . . ?
C14B C1B C6B C7B -2.8(14) . . . . ?
C5B C6B C7B C8B -178.6(10) . . . . ?
C1B C6B C7B C8B 3.8(15) . . . . ?
C6B C7B C8B C9B -3.0(16) . . . . ?
C7B C8B C9B C10B 177.4(11) . . . . ?
C7B C8B C9B C14B 1.2(16) . . . . ?
C14B C9B C10B C11B -1.6(17) . . . . ?
C8B C9B C10B C11B -177.8(12) . . . . ?
C9B C10B C11B C12B 0(2) . . . . ?
C10B C11B C12B N13B -0.1(19) . . . . ?
C10B C11B C12B C19B 178.7(12) . . . . ?
C11B C12B N13B C14B 2.4(17) . . . . ?
C19B C12B N13B C14B -176.5(9) . . . . ?
C11B C12B N13B Cu1B -158.2(9) . . . . ?
C19B C12B N13B Cu1B 22.9(16) . . . . ?
N2B Cu1B N13B C14B 22.6(7) . . . . ?
I1B Cu1B N13B C14B -134.3(6) . . . . ?
N2B Cu1B N13B C12B -174.9(11) . . . . ?
I1B Cu1B N13B C12B 28.2(12) . . . . ?
C12B N13B C14B C9B -4.4(16) . . . . ?
Cu1B N13B C14B C9B 160.5(8) . . . . ?
C12B N13B C14B C1B 176.2(9) . . . . ?
Cu1B N13B C14B C1B -18.9(11) . . . . ?
C10B C9B C14B N13B 4.0(16) . . . . ?
C8B C9B C14B N13B -179.7(9) . . . . ?
C10B C9B C14B C1B -176.6(10) . . . . ?
C8B C9B C14B C1B -0.3(15) . . . . ?
N2B C1B C14B N13B -0.7(14) . . . . ?
C6B C1B C14B N13B -179.4(9) . . . . ?
N2B C1B C14B C9B 179.9(9) . . . . ?
C6B C1B C14B C9B 1.1(14) . . . . ?
N2B C3B C15B C18B -32.0(13) . . . . ?
C4B C3B C15B C18B 148.5(10) . . . . ?
N2B C3B C15B C16B -152.8(9) . . . . ?
C4B C3B C15B C16B 27.7(14) . . . . ?
N2B C3B C15B C17B 88.9(11) . . . . ?
C4B C3B C15B C17B -90.6(12) . . . . ?
N13B C12B C19B C21B -84.2(13) . . . . ?
C11B C12B C19B C21B 97.0(14) . . . . ?
N13B C12B C19B C20B 38.2(14) . . . . ?
C11B C12B C19B C20B -140.7(12) . . . . ?
N13B C12B C19B C22B 155.9(12) . . . . ?
C11B C12B C19B C22B -23.0(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.207
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.108
#=============================================================================
#  end of cif data for "fro5846" (compound 1)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
