# Electronic Supplementary Material (ESI) for ChemComm.
# 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_chxdamcu
_database_code_depnum_ccdc_archive 'CCDC 1038527'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(R,R)-trans-N,N'-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine -CuCl2 complex"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H50 Cl2 Cu N2 O2'
_chemical_formula_weight         725.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'C 2 '

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

_cell_length_a                   13.608(3)
_cell_length_b                   10.347(2)
_cell_length_c                   14.528(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.341(3)
_cell_angle_gamma                90.00
_cell_volume                     1817.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             766
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.8401
_exptl_absorpt_correction_T_max  0.9048
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7381
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4090
_reflns_number_gt                3676
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0016P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4090
_refine_ls_number_parameters     288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0374
_refine_ls_wR_factor_gt          0.0371
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.866
_refine_ls_shift/su_max          0.004
_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 0.93688(13) 0.63355(16) 0.97260(13) 0.0097(4) Uani 1 1 d . . .
H1 H 0.9140(13) 0.6299(15) 0.8963(11) 0.012 Uiso 1 1 d . . .
C2 C 0.89242(15) 0.51400(16) 1.00135(15) 0.0131(4) Uani 1 1 d . . .
H2 H 0.8108(14) 0.5171(15) 0.9658(12) 0.016 Uiso 1 1 d . . .
H3 H 0.9127(13) 0.5130(15) 1.0750(13) 0.016 Uiso 1 1 d . . .
C3 C 0.93688(12) 0.3916(2) 0.97479(13) 0.0147(4) Uani 1 1 d . . .
H4 H 0.9106(14) 0.3169(15) 1.0016(13) 0.018 Uiso 1 1 d . . .
H5 H 0.9092(12) 0.398(2) 0.8985(11) 0.018 Uiso 1 1 d . . .
C4 C 0.77782(15) 0.78351(18) 0.93354(14) 0.0131(4) Uani 1 1 d . . .
H6 H 0.7380(13) 0.7163(15) 0.9550(12) 0.016 Uiso 1 1 d . . .
H7 H 0.7624(12) 0.8654(14) 0.9582(11) 0.016 Uiso 1 1 d . . .
C5 C 0.74384(13) 0.78966(16) 0.81988(13) 0.0133(4) Uani 1 1 d . . .
C6 C 0.69485(15) 0.68309(17) 0.75635(14) 0.0163(4) Uani 1 1 d . . .
H8 H 0.6854(14) 0.6088(16) 0.7851(12) 0.020 Uiso 1 1 d . . .
C7 C 0.66270(15) 0.68767(18) 0.65150(15) 0.0172(4) Uani 1 1 d . . .
H9 H 0.6301(14) 0.6129(17) 0.6090(12) 0.021 Uiso 1 1 d . . .
C8 C 0.67630(13) 0.79952(17) 0.60482(14) 0.0147(4) Uani 1 1 d . . .
C9 C 0.72357(12) 0.9066(2) 0.66816(13) 0.0173(4) Uani 1 1 d . . .
H10 H 0.7312(14) 0.9806(16) 0.6369(13) 0.021 Uiso 1 1 d . . .
C10 C 0.75711(12) 0.9014(2) 0.77356(12) 0.0156(3) Uani 1 1 d . . .
H11 H 0.7875(13) 0.9867(16) 0.8193(12) 0.019 Uiso 1 1 d . . .
C11 C 0.63780(14) 0.80328(18) 0.49089(14) 0.0166(4) Uani 1 1 d . . .
C12 C 0.64507(15) 0.69382(18) 0.43808(15) 0.0197(4) Uani 1 1 d . . .
H12 H 0.6796(14) 0.6165(16) 0.4765(12) 0.024 Uiso 1 1 d . . .
C13 C 0.60117(15) 0.69417(19) 0.33137(15) 0.0218(5) Uani 1 1 d . . .
H13 H 0.6046(15) 0.6219(16) 0.2963(13) 0.026 Uiso 1 1 d . . .
C14 C 0.55075(15) 0.8034(2) 0.27535(15) 0.0222(5) Uani 1 1 d . . .
H14 H 0.5203(15) 0.7987(17) 0.2039(14) 0.027 Uiso 1 1 d . . .
C15 C 0.54555(14) 0.9145(2) 0.32622(13) 0.0234(4) Uani 1 1 d . . .
H15 H 0.5100(14) 0.9996(16) 0.2834(13) 0.028 Uiso 1 1 d . . .
C16 C 0.58899(14) 0.9145(2) 0.43291(13) 0.0198(4) Uani 1 1 d . . .
H16 H 0.5872(14) 0.9803(17) 0.4657(14) 0.024 Uiso 1 1 d . . .
N1 N 0.89935(11) 0.75776(14) 0.99770(10) 0.0096(3) Uani 1 1 d . . .
H17 H 0.9115(13) 0.7549(17) 1.0595(12) 0.012 Uiso 1 1 d . . .
Cu1 Cu 1.0000 0.90116(2) 1.0000 0.01268(8) Uani 1 2 d S . .
Cl1 Cl 0.93323(4) 1.04091(4) 1.07497(4) 0.02000(12) Uani 1 1 d . . .
O1 O 1.07454(10) 0.71795(11) 0.79057(9) 0.0194(3) Uani 1 1 d . . .
C17 C 0.97763(18) 0.7812(2) 0.71293(17) 0.0269(5) Uani 1 1 d . . .
H18 H 0.9542(15) 0.8464(15) 0.7447(13) 0.032 Uiso 1 1 d . . .
H19 H 0.9184(16) 0.7287(19) 0.6889(14) 0.032 Uiso 1 1 d . . .
C18 C 1.0071(3) 0.8375(3) 0.6348(2) 0.0556(8) Uani 1 1 d . . .
H20 H 0.9513(19) 0.840(2) 0.5677(17) 0.067 Uiso 1 1 d . . .
H21 H 1.010(2) 0.922(2) 0.643(2) 0.067 Uiso 1 1 d . . .
C19 C 1.1232(2) 0.7898(3) 0.66522(19) 0.0407(6) Uani 1 1 d . . .
H22 H 1.1652(17) 0.8447(18) 0.6525(16) 0.049 Uiso 1 1 d . . .
H23 H 1.1191(18) 0.706(2) 0.6303(16) 0.049 Uiso 1 1 d . . .
C20 C 1.16708(18) 0.7665(2) 0.78049(17) 0.0266(5) Uani 1 1 d . . .
H24 H 1.2311(16) 0.7103(17) 0.8154(13) 0.032 Uiso 1 1 d . . .
H25 H 1.1912(14) 0.8498(15) 0.8189(13) 0.032 Uiso 1 1 d . . .


_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 1.489(2) . ?
C1 C2 1.517(2) . ?
C1 C1 1.526(3) 2_757 ?
C1 H1 1.005(14) . ?
C2 C3 1.527(3) . ?
C2 H2 0.987(16) . ?
C2 H3 0.974(17) . ?
C3 C3 1.527(3) 2_757 ?
C3 H4 1.002(16) . ?
C3 H5 0.995(14) . ?
C4 C5 1.498(2) . ?
C4 N1 1.503(2) . ?
C4 H6 1.015(16) . ?
C4 H7 0.980(14) . ?
C5 C10 1.391(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.379(2) . ?
C6 H8 0.912(16) . ?
C7 C8 1.396(2) . ?
C7 H9 0.962(18) . ?
C8 C9 1.394(3) . ?
C8 C11 1.490(2) . ?
C9 C10 1.383(2) . ?
C9 H10 0.920(16) . ?
C10 H11 1.066(16) . ?
C11 C12 1.397(2) . ?
C11 C16 1.400(3) . ?
C12 C13 1.382(2) . ?
C12 H12 0.965(16) . ?
C13 C14 1.378(2) . ?
C13 H13 0.918(16) . ?
C14 C15 1.386(3) . ?
C14 H14 0.926(17) . ?
C15 C16 1.382(2) . ?
C15 H15 1.059(16) . ?
C16 H16 0.838(17) . ?
N1 Cu1 2.0091(15) . ?
N1 H17 0.835(15) . ?
Cu1 N1 2.0091(15) 2_757 ?
Cu1 Cl1 2.2387(6) . ?
Cu1 Cl1 2.2387(6) 2_757 ?
O1 C20 1.425(2) . ?
O1 C17 1.440(2) . ?
C17 C18 1.486(4) . ?
C17 H18 0.951(18) . ?
C17 H19 0.899(19) . ?
C18 C19 1.514(4) . ?
C18 H20 0.92(2) . ?
C18 H21 0.88(2) . ?
C19 C20 1.517(3) . ?
C19 H22 0.88(2) . ?
C19 H23 1.00(2) . ?
C20 H24 0.974(19) . ?
C20 H25 0.996(16) . ?

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 114.29(14) . . ?
N1 C1 C1 107.62(10) . 2_757 ?
C2 C1 C1 110.61(11) . 2_757 ?
N1 C1 H1 109.6(9) . . ?
C2 C1 H1 108.2(9) . . ?
C1 C1 H1 106.2(10) 2_757 . ?
C1 C2 C3 110.61(15) . . ?
C1 C2 H2 108.9(9) . . ?
C3 C2 H2 112.1(9) . . ?
C1 C2 H3 111.3(10) . . ?
C3 C2 H3 108.8(10) . . ?
H2 C2 H3 105.0(13) . . ?
C3 C3 C2 111.57(11) 2_757 . ?
C3 C3 H4 109.7(10) 2_757 . ?
C2 C3 H4 106.8(10) . . ?
C3 C3 H5 107.5(9) 2_757 . ?
C2 C3 H5 103.6(12) . . ?
H4 C3 H5 117.6(15) . . ?
C5 C4 N1 112.70(14) . . ?
C5 C4 H6 115.5(9) . . ?
N1 C4 H6 106.2(9) . . ?
C5 C4 H7 110.9(9) . . ?
N1 C4 H7 106.6(9) . . ?
H6 C4 H7 104.2(12) . . ?
C10 C5 C6 117.77(17) . . ?
C10 C5 C4 121.72(15) . . ?
C6 C5 C4 120.50(16) . . ?
C7 C6 C5 121.08(17) . . ?
C7 C6 H8 119.6(10) . . ?
C5 C6 H8 119.3(10) . . ?
C6 C7 C8 121.30(18) . . ?
C6 C7 H9 120.0(10) . . ?
C8 C7 H9 118.7(10) . . ?
C9 C8 C7 117.51(17) . . ?
C9 C8 C11 122.19(16) . . ?
C7 C8 C11 120.27(16) . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H10 121.6(11) . . ?
C8 C9 H10 117.3(11) . . ?
C9 C10 C5 121.15(19) . . ?
C9 C10 H11 119.6(9) . . ?
C5 C10 H11 119.0(9) . . ?
C12 C11 C16 118.02(17) . . ?
C12 C11 C8 120.77(16) . . ?
C16 C11 C8 121.15(17) . . ?
C13 C12 C11 120.72(18) . . ?
C13 C12 H12 119.8(10) . . ?
C11 C12 H12 119.5(10) . . ?
C14 C13 C12 120.42(18) . . ?
C14 C13 H13 118.6(12) . . ?
C12 C13 H13 121.0(12) . . ?
C13 C14 C15 119.94(19) . . ?
C13 C14 H14 117.7(12) . . ?
C15 C14 H14 122.4(12) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.3(10) . . ?
C14 C15 H15 119.9(10) . . ?
C15 C16 C11 120.99(19) . . ?
C15 C16 H16 121.9(13) . . ?
C11 C16 H16 117.1(13) . . ?
C1 N1 C4 113.87(13) . . ?
C1 N1 Cu1 109.50(10) . . ?
C4 N1 Cu1 115.28(11) . . ?
C1 N1 H17 108.2(13) . . ?
C4 N1 H17 106.9(12) . . ?
Cu1 N1 H17 102.2(12) . . ?
N1 Cu1 N1 84.78(8) 2_757 . ?
N1 Cu1 Cl1 153.48(4) 2_757 . ?
N1 Cu1 Cl1 93.40(4) . . ?
N1 Cu1 Cl1 93.40(4) 2_757 2_757 ?
N1 Cu1 Cl1 153.48(4) . 2_757 ?
Cl1 Cu1 Cl1 99.53(3) . 2_757 ?
C20 O1 C17 107.08(15) . . ?
O1 C17 C18 107.78(19) . . ?
O1 C17 H18 109.4(11) . . ?
C18 C17 H18 111.2(11) . . ?
O1 C17 H19 111.4(12) . . ?
C18 C17 H19 116.7(13) . . ?
H18 C17 H19 100.1(16) . . ?
C17 C18 C19 105.1(2) . . ?
C17 C18 H20 116.0(16) . . ?
C19 C18 H20 124.0(15) . . ?
C17 C18 H21 107(2) . . ?
C19 C18 H21 108(2) . . ?
H20 C18 H21 95(2) . . ?
C18 C19 C20 101.7(2) . . ?
C18 C19 H22 114.7(14) . . ?
C20 C19 H22 111.6(14) . . ?
C18 C19 H23 109.2(14) . . ?
C20 C19 H23 109.0(12) . . ?
H22 C19 H23 110.2(17) . . ?
O1 C20 C19 104.54(17) . . ?
O1 C20 H24 110.9(11) . . ?
C19 C20 H24 118.3(11) . . ?
O1 C20 H25 109.1(11) . . ?
C19 C20 H25 110.0(10) . . ?
H24 C20 H25 103.8(14) . . ?

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 -178.91(13) . . . . ?
C1 C1 C2 C3 -57.3(2) 2_757 . . . ?
C1 C2 C3 C3 54.9(2) . . . 2_757 ?
N1 C4 C5 C10 -82.2(2) . . . . ?
N1 C4 C5 C6 99.39(19) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C4 C5 C6 C7 179.69(17) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C11 -178.16(17) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C11 C8 C9 C10 178.95(16) . . . . ?
C8 C9 C10 C5 -0.7(2) . . . . ?
C6 C5 C10 C9 -0.4(2) . . . . ?
C4 C5 C10 C9 -178.84(15) . . . . ?
C9 C8 C11 C12 146.54(17) . . . . ?
C7 C8 C11 C12 -35.4(3) . . . . ?
C9 C8 C11 C16 -36.2(3) . . . . ?
C7 C8 C11 C16 141.77(18) . . . . ?
C16 C11 C12 C13 -2.6(3) . . . . ?
C8 C11 C12 C13 174.68(17) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 2.4(3) . . . . ?
C8 C11 C16 C15 -174.90(16) . . . . ?
C2 C1 N1 C4 -67.76(18) . . . . ?
C1 C1 N1 C4 168.97(15) 2_757 . . . ?
C2 C1 N1 Cu1 161.55(11) . . . . ?
C1 C1 N1 Cu1 38.28(17) 2_757 . . . ?
C5 C4 N1 C1 -59.95(19) . . . . ?
C5 C4 N1 Cu1 67.83(16) . . . . ?
C1 N1 Cu1 N1 -13.97(7) . . . 2_757 ?
C4 N1 Cu1 N1 -143.90(13) . . . 2_757 ?
C1 N1 Cu1 Cl1 -167.43(9) . . . . ?
C4 N1 Cu1 Cl1 62.63(11) . . . . ?
C1 N1 Cu1 Cl1 73.19(14) . . . 2_757 ?
C4 N1 Cu1 Cl1 -56.74(16) . . . 2_757 ?
C20 O1 C17 C18 17.5(2) . . . . ?
O1 C17 C18 C19 6.3(3) . . . . ?
C17 C18 C19 C20 -25.8(3) . . . . ?
C17 O1 C20 C19 -34.2(2) . . . . ?
C18 C19 C20 O1 36.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H17 O1 0.835(15) 2.132(16) 2.959(2) 170.1(17) 2_757

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# 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_tana_1_12_b_0m
_database_code_depnum_ccdc_archive 'CCDC 1042149'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C72 H84 Cl4 Cu2 N4 O4'
_chemical_formula_weight         1338.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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)

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

_cell_length_a                   13.8568(3)
_cell_length_b                   15.8847(4)
_cell_length_c                   15.2073(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0460(10)
_cell_angle_gamma                90.00
_cell_volume                     3328.68(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      67.88

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2045
_exptl_absorpt_correction_T_max  0.4627
_exptl_absorpt_process_details   sadabs
_chemical_absolute_configuration syn

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35306
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         67.55
_reflns_number_total             9740
_reflns_number_gt                9703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0388P)²+0.8642P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.059(9)
_refine_ls_number_reflns         9740
_refine_ls_number_parameters     795
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.201858(18) 0.273165(17) -0.000666(17) 0.01509(8) Uani 1 1 d . . .
Cu2 Cu 0.697799(19) 0.072386(17) 1.003697(18) 0.01519(8) Uani 1 1 d . . .
Cl1 Cl -0.33584(3) 0.33180(3) -0.07735(3) 0.01947(11) Uani 1 1 d . . .
Cl2 Cl -0.28623(3) 0.22241(3) 0.10754(3) 0.01917(11) Uani 1 1 d . . .
Cl3 Cl 0.83058(3) 0.01646(3) 1.08145(3) 0.02053(11) Uani 1 1 d . . .
Cl4 Cl 0.78145(3) 0.12360(3) 0.89455(3) 0.01967(11) Uani 1 1 d . . .
O1 O 0.67934(13) 0.02441(16) 0.26391(11) 0.0395(5) Uani 1 1 d . . .
O2 O 0.70783(14) 0.11972(14) 0.37139(11) 0.0380(4) Uani 1 1 d . . .
O3 O 0.78264(15) 0.21275(14) 0.62666(12) 0.0406(5) Uani 1 1 d . . .
O4 O 0.81737(15) 0.31128(15) 0.73032(11) 0.0399(5) Uani 1 1 d . . .
N1 N -0.07186(12) 0.22166(15) 0.05485(12) 0.0160(4) Uani 1 1 d . . .
N2 N -0.11859(12) 0.33450(13) -0.08026(11) 0.0161(4) Uani 1 1 d . . .
N3 N 0.57179(12) 0.12735(13) 0.95109(11) 0.0155(4) Uani 1 1 d . . .
N4 N 0.60955(12) 0.00043(12) 1.07080(11) 0.0152(4) Uani 1 1 d . . .
C1 C 0.00762(14) 0.24529(14) 0.00077(13) 0.0157(4) Uani 1 1 d . . .
H1 H 0.0458 0.2921 0.0316 0.019 Uiso 1 1 calc R . .
C2 C 0.07719(14) 0.17293(15) -0.01331(14) 0.0209(4) Uani 1 1 d . . .
H2C H 0.0403 0.1253 -0.0423 0.025 Uiso 1 1 calc R . .
H2D H 0.1081 0.1532 0.0447 0.025 Uiso 1 1 calc R . .
C3 C 0.15567(17) 0.20100(18) -0.07070(16) 0.0277(5) Uani 1 1 d . . .
H3C H 0.1979 0.2432 -0.0379 0.033 Uiso 1 1 calc R . .
H3D H 0.1964 0.1520 -0.0826 0.033 Uiso 1 1 calc R . .
C4 C 0.11256(15) 0.23893(17) -0.15845(14) 0.0290(5) Uani 1 1 d . . .
H4C H 0.0769 0.1949 -0.1948 0.035 Uiso 1 1 calc R . .
H4D H 0.1654 0.2602 -0.1914 0.035 Uiso 1 1 calc R . .
C5 C 0.04335(15) 0.31124(17) -0.14211(14) 0.0220(5) Uani 1 1 d . . .
H5A H 0.0794 0.3570 -0.1088 0.026 Uiso 1 1 calc R . .
H5B H 0.0139 0.3344 -0.1992 0.026 Uiso 1 1 calc R . .
C6 C -0.03555(13) 0.27707(13) -0.08926(12) 0.0159(4) Uani 1 1 d . . .
H6 H -0.0632 0.2266 -0.1222 0.019 Uiso 1 1 calc R . .
C7 C -0.09682(15) 0.42408(14) -0.05642(13) 0.0192(4) Uani 1 1 d . . .
H7A H -0.1506 0.4597 -0.0835 0.023 Uiso 1 1 calc R . .
H7B H -0.0371 0.4411 -0.0823 0.023 Uiso 1 1 calc R . .
C8 C -0.08298(15) 0.44123(14) 0.04231(14) 0.0177(4) Uani 1 1 d . . .
C9 C 0.00888(15) 0.45943(15) 0.08536(14) 0.0206(4) Uani 1 1 d . . .
H9 H 0.0639 0.4591 0.0530 0.025 Uiso 1 1 calc R . .
C10 C 0.02023(15) 0.47795(15) 0.17522(15) 0.0221(5) Uani 1 1 d . . .
H10 H 0.0833 0.4897 0.2034 0.027 Uiso 1 1 calc R . .
C11 C -0.05861(16) 0.47970(15) 0.22479(14) 0.0213(5) Uani 1 1 d . . .
C12 C -0.15021(15) 0.46171(17) 0.18090(15) 0.0231(5) Uani 1 1 d . . .
H12 H -0.2054 0.4620 0.2131 0.028 Uiso 1 1 calc R . .
C13 C -0.16183(16) 0.44344(16) 0.09097(15) 0.0211(5) Uani 1 1 d . . .
H13 H -0.2249 0.4323 0.0625 0.025 Uiso 1 1 calc R . .
C14 C -0.04727(16) 0.50185(16) 0.32002(14) 0.0236(5) Uani 1 1 d . . .
C15 C -0.11375(17) 0.47443(18) 0.37700(16) 0.0277(5) Uani 1 1 d . . .
H15 H -0.1660 0.4391 0.3548 0.033 Uiso 1 1 calc R . .
C16 C -0.10465(19) 0.4980(2) 0.46552(16) 0.0331(6) Uani 1 1 d . . .
H16 H -0.1510 0.4794 0.5030 0.040 Uiso 1 1 calc R . .
C17 C -0.0283(2) 0.54863(19) 0.49922(16) 0.0360(6) Uani 1 1 d . . .
H17 H -0.0223 0.5649 0.5597 0.043 Uiso 1 1 calc R . .
C18 C 0.0391(2) 0.5754(2) 0.44449(16) 0.0368(6) Uani 1 1 d . . .
H18 H 0.0923 0.6093 0.4677 0.044 Uiso 1 1 calc R . .
C19 C 0.02937(18) 0.55292(18) 0.35550(15) 0.0307(5) Uani 1 1 d . . .
H19 H 0.0755 0.5726 0.3183 0.037 Uiso 1 1 calc R . .
C20 C -0.04967(14) 0.24037(15) 0.15103(13) 0.0194(4) Uani 1 1 d . . .
H20A H -0.1081 0.2275 0.1808 0.023 Uiso 1 1 calc R . .
H20B H -0.0371 0.3015 0.1578 0.023 Uiso 1 1 calc R . .
C21 C 0.03544(15) 0.19353(15) 0.19864(13) 0.0186(5) Uani 1 1 d . . .
C22 C 0.12107(15) 0.23599(17) 0.22796(15) 0.0228(5) Uani 1 1 d . . .
H22 H 0.1279 0.2938 0.2137 0.027 Uiso 1 1 calc R . .
C23 C 0.19693(16) 0.19427(16) 0.27803(15) 0.0239(5) Uani 1 1 d . . .
H23 H 0.2548 0.2241 0.2970 0.029 Uiso 1 1 calc R . .
C24 C 0.18901(16) 0.11038(16) 0.30030(13) 0.0194(4) Uani 1 1 d . . .
C25 C 0.10420(15) 0.06788(17) 0.26856(13) 0.0230(5) Uani 1 1 d . . .
H25 H 0.0980 0.0097 0.2813 0.028 Uiso 1 1 calc R . .
C26 C 0.02915(16) 0.10889(16) 0.21895(14) 0.0234(5) Uani 1 1 d . . .
H26 H -0.0278 0.0784 0.1984 0.028 Uiso 1 1 calc R . .
C27 C 0.26390(15) 0.06708(17) 0.36207(13) 0.0205(5) Uani 1 1 d . . .
C28 C 0.27978(18) -0.01915(17) 0.35579(17) 0.0267(5) Uani 1 1 d . . .
H28 H 0.2490 -0.0497 0.3069 0.032 Uiso 1 1 calc R . .
C29 C 0.34012(18) -0.06096(19) 0.42026(17) 0.0330(6) Uani 1 1 d . . .
H29 H 0.3503 -0.1198 0.4153 0.040 Uiso 1 1 calc R . .
C30 C 0.38589(18) -0.0168(2) 0.49234(17) 0.0320(6) Uani 1 1 d . . .
H30 H 0.4245 -0.0458 0.5381 0.038 Uiso 1 1 calc R . .
C31 C 0.37438(17) 0.0693(2) 0.49640(16) 0.0309(6) Uani 1 1 d . . .
H31 H 0.4077 0.1003 0.5437 0.037 Uiso 1 1 calc R . .
C32 C 0.31432(16) 0.11083(17) 0.43167(15) 0.0245(5) Uani 1 1 d . . .
H32 H 0.3075 0.1702 0.4349 0.029 Uiso 1 1 calc R . .
C33 C 0.50748(13) 0.12177(14) 1.02344(12) 0.0160(4) Uani 1 1 d . . .
H33 H 0.5383 0.1569 1.0733 0.019 Uiso 1 1 calc R . .
C34 C 0.50752(13) 0.03145(13) 1.05692(12) 0.0158(4) Uani 1 1 d . . .
H34 H 0.4709 -0.0042 1.0105 0.019 Uiso 1 1 calc R . .
C35 C 0.61788(15) -0.09205(15) 1.05596(13) 0.0191(4) Uani 1 1 d . . .
H35A H 0.5686 -0.1219 1.0869 0.023 Uiso 1 1 calc R . .
H35B H 0.6828 -0.1116 1.0813 0.023 Uiso 1 1 calc R . .
C36 C 0.60349(15) -0.11324(14) 0.95877(14) 0.0177(4) Uani 1 1 d . . .
C37 C 0.67933(15) -0.10472(15) 0.90584(15) 0.0203(5) Uani 1 1 d . . .
H37 H 0.7416 -0.0875 0.9318 0.024 Uiso 1 1 calc R . .
C38 C 0.66488(15) -0.12117(16) 0.81551(14) 0.0214(5) Uani 1 1 d . . .
H38 H 0.7175 -0.1150 0.7807 0.026 Uiso 1 1 calc R . .
C39 C 0.57432(15) -0.14665(14) 0.77505(14) 0.0193(4) Uani 1 1 d . . .
C40 C 0.49923(15) -0.15586(14) 0.82872(14) 0.0207(4) Uani 1 1 d . . .
H40 H 0.4371 -0.1736 0.8030 0.025 Uiso 1 1 calc R . .
C41 C 0.51336(15) -0.13976(14) 0.91865(14) 0.0201(4) Uani 1 1 d . . .
H41 H 0.4610 -0.1469 0.9535 0.024 Uiso 1 1 calc R . .
C42 C 0.55998(15) -0.16759(16) 0.67829(14) 0.0219(4) Uani 1 1 d . . .
C43 C 0.62164(16) -0.13587(17) 0.62005(15) 0.0256(5) Uani 1 1 d . . .
H43 H 0.6724 -0.0986 0.6413 0.031 Uiso 1 1 calc R . .
C44 C 0.61025(19) -0.1579(2) 0.53086(16) 0.0321(6) Uani 1 1 d . . .
H44 H 0.6548 -0.1375 0.4925 0.039 Uiso 1 1 calc R . .
C45 C 0.53435(19) -0.2093(2) 0.49808(16) 0.0344(6) Uani 1 1 d . . .
H45 H 0.5254 -0.2232 0.4370 0.041 Uiso 1 1 calc R . .
C46 C 0.4720(2) -0.24013(19) 0.55509(16) 0.0349(6) Uani 1 1 d . . .
H46 H 0.4195 -0.2754 0.5330 0.042 Uiso 1 1 calc R . .
C47 C 0.48481(17) -0.22026(18) 0.64444(15) 0.0289(5) Uani 1 1 d . . .
H47 H 0.4417 -0.2429 0.6830 0.035 Uiso 1 1 calc R . .
C48 C 0.45622(15) 0.02651(16) 1.14104(14) 0.0207(5) Uani 1 1 d . . .
H48A H 0.4543 -0.0327 1.1610 0.025 Uiso 1 1 calc R . .
H48B H 0.4929 0.0597 1.1885 0.025 Uiso 1 1 calc R . .
C49 C 0.35310(14) 0.06066(15) 1.12405(14) 0.0244(5) Uani 1 1 d . . .
H49A H 0.3146 0.0241 1.0808 0.029 Uiso 1 1 calc R . .
H49B H 0.3221 0.0599 1.1798 0.029 Uiso 1 1 calc R . .
C50 C 0.35339(15) 0.14995(16) 1.08858(14) 0.0220(5) Uani 1 1 d . . .
H50A H 0.3880 0.1873 1.1335 0.026 Uiso 1 1 calc R . .
H50B H 0.2858 0.1704 1.0767 0.026 Uiso 1 1 calc R . .
C51 C 0.40302(14) 0.15338(15) 1.00342(14) 0.0192(4) Uani 1 1 d . . .
H51A H 0.4031 0.2119 0.9810 0.023 Uiso 1 1 calc R . .
H51B H 0.3675 0.1176 0.9575 0.023 Uiso 1 1 calc R . .
C52 C 0.53577(14) 0.08949(15) 0.86427(13) 0.0180(4) Uani 1 1 d . . .
H52A H 0.5109 0.0324 0.8752 0.022 Uiso 1 1 calc R . .
H52B H 0.5917 0.0828 0.8294 0.022 Uiso 1 1 calc R . .
C53 C 0.45681(15) 0.13750(15) 0.80820(13) 0.0180(4) Uani 1 1 d . . .
C54 C 0.37391(15) 0.09616(16) 0.77165(15) 0.0230(5) Uani 1 1 d . . .
H54 H 0.3658 0.0381 0.7838 0.028 Uiso 1 1 calc R . .
C55 C 0.30278(16) 0.13810(16) 0.71771(15) 0.0221(5) Uani 1 1 d . . .
H55 H 0.2469 0.1082 0.6934 0.027 Uiso 1 1 calc R . .
C56 C 0.31160(15) 0.22328(16) 0.69845(13) 0.0184(4) Uani 1 1 d . . .
C57 C 0.39514(15) 0.26515(16) 0.73613(14) 0.0227(5) Uani 1 1 d . . .
H57 H 0.4029 0.3235 0.7249 0.027 Uiso 1 1 calc R . .
C58 C 0.46687(16) 0.22252(17) 0.78972(14) 0.0230(5) Uani 1 1 d . . .
H58 H 0.5233 0.2519 0.8139 0.028 Uiso 1 1 calc R . .
C59 C 0.23881(15) 0.26856(17) 0.63767(14) 0.0211(5) Uani 1 1 d . . .
C60 C 0.18881(16) 0.22632(18) 0.56579(14) 0.0247(5) Uani 1 1 d . . .
H60 H 0.1959 0.1672 0.5599 0.030 Uiso 1 1 calc R . .
C61 C 0.12839(17) 0.2713(2) 0.50256(16) 0.0299(5) Uani 1 1 d . . .
H61 H 0.0965 0.2427 0.4529 0.036 Uiso 1 1 calc R . .
C62 C 0.11486(19) 0.3562(2) 0.51170(17) 0.0341(6) Uani 1 1 d . . .
H62 H 0.0745 0.3863 0.4681 0.041 Uiso 1 1 calc R . .
C63 C 0.16012(19) 0.39785(19) 0.58448(18) 0.0339(6) Uani 1 1 d . . .
H63 H 0.1495 0.4564 0.5916 0.041 Uiso 1 1 calc R . .
C64 C 0.22120(18) 0.35451(18) 0.64739(17) 0.0279(5) Uani 1 1 d . . .
H64 H 0.2513 0.3837 0.6975 0.034 Uiso 1 1 calc R . .
C65 C 0.65792(18) 0.05725(19) 0.33044(16) 0.0309(6) Uani 1 1 d . . .
C66 C 0.7940(2) 0.1480(2) 0.3325(2) 0.0462(8) Uani 1 1 d . . .
H66A H 0.7823 0.1462 0.2672 0.055 Uiso 1 1 calc R . .
H66B H 0.8496 0.1107 0.3515 0.055 Uiso 1 1 calc R . .
C67 C 0.8157(3) 0.2344(3) 0.3622(3) 0.0729(12) Uani 1 1 d . . .
H67A H 0.7697 0.2732 0.3299 0.109 Uiso 1 1 calc R . .
H67B H 0.8819 0.2491 0.3508 0.109 Uiso 1 1 calc R . .
H67C H 0.8099 0.2387 0.4257 0.109 Uiso 1 1 calc R . .
C68 C 0.5722(2) 0.0329(2) 0.37676(18) 0.0424(7) Uani 1 1 d . . .
H68A H 0.5276 0.0807 0.3769 0.064 Uiso 1 1 calc R . .
H68B H 0.5941 0.0167 0.4378 0.064 Uiso 1 1 calc R . .
H68C H 0.5388 -0.0147 0.3459 0.064 Uiso 1 1 calc R . .
C69 C 0.6677(3) 0.1034(3) 0.6367(3) 0.0694(12) Uani 1 1 d . . .
H69A H 0.6608 0.1025 0.5719 0.104 Uiso 1 1 calc R . .
H69B H 0.6056 0.0887 0.6581 0.104 Uiso 1 1 calc R . .
H69C H 0.7172 0.0626 0.6594 0.104 Uiso 1 1 calc R . .
C70 C 0.6973(2) 0.1890(2) 0.66824(18) 0.0433(7) Uani 1 1 d . . .
H70A H 0.6441 0.2296 0.6523 0.052 Uiso 1 1 calc R . .
H70B H 0.7121 0.1890 0.7334 0.052 Uiso 1 1 calc R . .
C71 C 0.83648(19) 0.2753(2) 0.66477(16) 0.0321(6) Uani 1 1 d . . .
C72 C 0.9217(2) 0.2960(2) 0.6157(2) 0.0504(8) Uani 1 1 d . . .
H72A H 0.9416 0.3543 0.6280 0.076 Uiso 1 1 calc R . .
H72B H 0.9036 0.2889 0.5521 0.076 Uiso 1 1 calc R . .
H72C H 0.9757 0.2581 0.6350 0.076 Uiso 1 1 calc R . .
H1N H -0.0816(17) 0.176(2) 0.0475(16) 0.012(7) Uiso 1 1 d . . .
H3N H 0.5869(16) 0.1812(19) 0.9431(15) 0.012(6) Uiso 1 1 d . . .
H2N H -0.1551(17) 0.3371(18) -0.1302(17) 0.021(6) Uiso 1 1 d . . .
H4N H 0.6308(15) 0.0105(15) 1.1246(15) 0.007(5) Uiso 1 1 d . . .


_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 N2 2.0099(18) . ?
Cu1 N1 2.0753(18) . ?
Cu1 Cl2 2.2649(5) . ?
Cu1 Cl1 2.2844(5) . ?
Cu2 N4 2.0263(18) . ?
Cu2 N3 2.0388(17) . ?
Cu2 Cl3 2.2615(5) . ?
Cu2 Cl4 2.2729(5) . ?
O1 C65 1.203(3) . ?
O2 C65 1.327(4) . ?
O2 C66 1.458(4) . ?
O3 C71 1.338(4) . ?
O3 C70 1.448(3) . ?
O4 C71 1.202(3) . ?
N1 C1 1.490(3) . ?
N1 C20 1.492(3) . ?
N1 H1N 0.74(3) . ?
N2 C6 1.486(3) . ?
N2 C7 1.491(3) . ?
N2 H2N 0.87(3) . ?
N3 C52 1.488(3) . ?
N3 C33 1.490(3) . ?
N3 H3N 0.89(3) . ?
N4 C34 1.491(2) . ?
N4 C35 1.493(3) . ?
N4 H4N 0.86(2) . ?
C1 C6 1.521(3) . ?
C1 C2 1.530(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.531(3) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 C5 1.533(3) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C7 C8 1.518(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.383(3) . ?
C8 C9 1.399(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(3) . ?
C11 C14 1.483(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.399(3) . ?
C14 C15 1.399(4) . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.513(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.384(4) . ?
C21 C22 1.397(3) . ?
C22 C23 1.398(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.397(3) . ?
C24 C27 1.492(3) . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.391(3) . ?
C27 C28 1.392(4) . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.396(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.522(3) . ?
C33 C51 1.532(3) . ?
C33 H33 1.0000 . ?
C34 C48 1.529(3) . ?
C34 H34 1.0000 . ?
C35 C36 1.509(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.396(3) . ?
C36 C41 1.396(3) . ?
C37 C38 1.392(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.398(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.396(3) . ?
C39 C42 1.501(3) . ?
C40 C41 1.385(3) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 C43 1.388(3) . ?
C42 C47 1.392(3) . ?
C43 C44 1.393(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.383(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.377(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.388(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.525(3) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.518(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.530(3) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.520(3) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.387(3) . ?
C53 C58 1.389(4) . ?
C54 C55 1.385(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.392(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.404(3) . ?
C56 C59 1.481(3) . ?
C57 C58 1.393(3) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C59 C64 1.398(4) . ?
C59 C60 1.402(3) . ?
C60 C61 1.403(3) . ?
C60 H60 0.9500 . ?
C61 C62 1.370(5) . ?
C61 H61 0.9500 . ?
C62 C63 1.382(4) . ?
C62 H62 0.9500 . ?
C63 C64 1.391(4) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?
C65 C68 1.494(4) . ?
C66 C67 1.465(6) . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 C70 1.484(6) . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C70 H70A 0.9900 . ?
C70 H70B 0.9900 . ?
C71 C72 1.498(4) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 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
N2 Cu1 N1 84.68(7) . . ?
N2 Cu1 Cl2 169.44(6) . . ?
N1 Cu1 Cl2 93.24(5) . . ?
N2 Cu1 Cl1 88.98(5) . . ?
N1 Cu1 Cl1 172.93(5) . . ?
Cl2 Cu1 Cl1 93.558(19) . . ?
N4 Cu2 N3 84.37(7) . . ?
N4 Cu2 Cl3 90.92(5) . . ?
N3 Cu2 Cl3 171.63(5) . . ?
N4 Cu2 Cl4 161.97(6) . . ?
N3 Cu2 Cl4 92.39(5) . . ?
Cl3 Cu2 Cl4 94.19(2) . . ?
C65 O2 C66 116.7(2) . . ?
C71 O3 C70 116.6(2) . . ?
C1 N1 C20 113.75(16) . . ?
C1 N1 Cu1 109.66(13) . . ?
C20 N1 Cu1 113.61(14) . . ?
C1 N1 H1N 107(2) . . ?
C20 N1 H1N 111(2) . . ?
Cu1 N1 H1N 100.8(19) . . ?
C6 N2 C7 117.99(16) . . ?
C6 N2 Cu1 104.90(13) . . ?
C7 N2 Cu1 115.49(13) . . ?
C6 N2 H2N 109.5(17) . . ?
C7 N2 H2N 104.6(19) . . ?
Cu1 N2 H2N 103.4(17) . . ?
C52 N3 C33 117.41(16) . . ?
C52 N3 Cu2 111.61(13) . . ?
C33 N3 Cu2 103.82(12) . . ?
C52 N3 H3N 109.2(15) . . ?
C33 N3 H3N 108.9(15) . . ?
Cu2 N3 H3N 105.1(15) . . ?
C34 N4 C35 113.02(16) . . ?
C34 N4 Cu2 110.85(13) . . ?
C35 N4 Cu2 114.75(13) . . ?
C34 N4 H4N 107.4(14) . . ?
C35 N4 H4N 107.7(16) . . ?
Cu2 N4 H4N 102.2(15) . . ?
N1 C1 C6 109.68(15) . . ?
N1 C1 C2 113.65(18) . . ?
C6 C1 C2 108.49(17) . . ?
N1 C1 H1 108.3 . . ?
C6 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C1 C2 C3 110.92(19) . . ?
C1 C2 H2C 109.5 . . ?
C3 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
C3 C2 H2D 109.5 . . ?
H2C C2 H2D 108.0 . . ?
C4 C3 C2 112.16(18) . . ?
C4 C3 H3C 109.2 . . ?
C2 C3 H3C 109.2 . . ?
C4 C3 H3D 109.2 . . ?
C2 C3 H3D 109.2 . . ?
H3C C3 H3D 107.9 . . ?
C3 C4 C5 110.34(19) . . ?
C3 C4 H4C 109.6 . . ?
C5 C4 H4C 109.6 . . ?
C3 C4 H4D 109.6 . . ?
C5 C4 H4D 109.6 . . ?
H4C C4 H4D 108.1 . . ?
C6 C5 C4 108.3(2) . . ?
C6 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C1 110.84(15) . . ?
N2 C6 C5 115.82(18) . . ?
C1 C6 C5 110.92(15) . . ?
N2 C6 H6 106.2 . . ?
C1 C6 H6 106.2 . . ?
C5 C6 H6 106.2 . . ?
N2 C7 C8 114.39(18) . . ?
N2 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C13 C8 C9 118.4(2) . . ?
C13 C8 C7 120.60(19) . . ?
C9 C8 C7 120.92(19) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 121.52(19) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C12 117.5(2) . . ?
C10 C11 C14 121.7(2) . . ?
C12 C11 C14 120.8(2) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C8 C13 C12 121.0(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C19 C14 C15 117.7(2) . . ?
C19 C14 C11 120.8(2) . . ?
C15 C14 C11 121.5(2) . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
N1 C20 C21 116.16(18) . . ?
N1 C20 H20A 108.2 . . ?
C21 C20 H20A 108.2 . . ?
N1 C20 H20B 108.2 . . ?
C21 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C26 C21 C22 118.0(2) . . ?
C26 C21 C20 121.4(2) . . ?
C22 C21 C20 120.6(2) . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 117.8(2) . . ?
C23 C24 C27 122.1(2) . . ?
C25 C24 C27 119.9(2) . . ?
C26 C25 C24 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C21 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C32 C27 C28 118.2(2) . . ?
C32 C27 C24 120.6(2) . . ?
C28 C27 C24 121.0(2) . . ?
C29 C28 C27 120.7(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.2(2) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
N3 C33 C34 108.90(16) . . ?
N3 C33 C51 117.38(15) . . ?
C34 C33 C51 110.03(16) . . ?
N3 C33 H33 106.7 . . ?
C34 C33 H33 106.7 . . ?
C51 C33 H33 106.7 . . ?
N4 C34 C33 109.01(16) . . ?
N4 C34 C48 112.46(15) . . ?
C33 C34 C48 110.13(17) . . ?
N4 C34 H34 108.4 . . ?
C33 C34 H34 108.4 . . ?
C48 C34 H34 108.4 . . ?
N4 C35 C36 111.30(18) . . ?
N4 C35 H35A 109.4 . . ?
C36 C35 H35A 109.4 . . ?
N4 C35 H35B 109.4 . . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C41 118.06(19) . . ?
C37 C36 C35 120.90(19) . . ?
C41 C36 C35 121.02(19) . . ?
C38 C37 C36 120.8(2) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C39 121.2(2) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C40 C39 C38 117.56(19) . . ?
C40 C39 C42 121.32(19) . . ?
C38 C39 C42 121.04(19) . . ?
C41 C40 C39 121.43(19) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C36 120.94(19) . . ?
C40 C41 H41 119.5 . . ?
C36 C41 H41 119.5 . . ?
C43 C42 C47 118.0(2) . . ?
C43 C42 C39 121.2(2) . . ?
C47 C42 C39 120.8(2) . . ?
C42 C43 C44 121.0(2) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C45 C44 C43 120.2(2) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C46 C45 C44 119.1(2) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 120.8(3) . . ?
C45 C46 H46 119.6 . . ?
C47 C46 H46 119.6 . . ?
C46 C47 C42 120.8(2) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
C49 C48 C34 110.48(17) . . ?
C49 C48 H48A 109.6 . . ?
C34 C48 H48A 109.6 . . ?
C49 C48 H48B 109.6 . . ?
C34 C48 H48B 109.6 . . ?
H48A C48 H48B 108.1 . . ?
C50 C49 C48 110.80(18) . . ?
C50 C49 H49A 109.5 . . ?
C48 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 108.1 . . ?
C49 C50 C51 110.64(19) . . ?
C49 C50 H50A 109.5 . . ?
C51 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C51 C50 H50B 109.5 . . ?
H50A C50 H50B 108.1 . . ?
C50 C51 C33 108.64(17) . . ?
C50 C51 H51A 110.0 . . ?
C33 C51 H51A 110.0 . . ?
C50 C51 H51B 110.0 . . ?
C33 C51 H51B 110.0 . . ?
H51A C51 H51B 108.3 . . ?
N3 C52 C53 116.70(18) . . ?
N3 C52 H52A 108.1 . . ?
C53 C52 H52A 108.1 . . ?
N3 C52 H52B 108.1 . . ?
C53 C52 H52B 108.1 . . ?
H52A C52 H52B 107.3 . . ?
C54 C53 C58 118.4(2) . . ?
C54 C53 C52 120.3(2) . . ?
C58 C53 C52 121.3(2) . . ?
C55 C54 C53 121.1(2) . . ?
C55 C54 H54 119.4 . . ?
C53 C54 H54 119.4 . . ?
C54 C55 C56 121.3(2) . . ?
C54 C55 H55 119.4 . . ?
C56 C55 H55 119.4 . . ?
C55 C56 C57 117.5(2) . . ?
C55 C56 C59 122.3(2) . . ?
C57 C56 C59 120.2(2) . . ?
C58 C57 C56 121.0(2) . . ?
C58 C57 H57 119.5 . . ?
C56 C57 H57 119.5 . . ?
C53 C58 C57 120.7(2) . . ?
C53 C58 H58 119.7 . . ?
C57 C58 H58 119.7 . . ?
C64 C59 C60 118.2(2) . . ?
C64 C59 C56 121.6(2) . . ?
C60 C59 C56 120.2(2) . . ?
C59 C60 C61 120.1(3) . . ?
C59 C60 H60 120.0 . . ?
C61 C60 H60 120.0 . . ?
C62 C61 C60 120.7(3) . . ?
C62 C61 H61 119.7 . . ?
C60 C61 H61 119.7 . . ?
C61 C62 C63 119.8(2) . . ?
C61 C62 H62 120.1 . . ?
C63 C62 H62 120.1 . . ?
C62 C63 C64 120.4(3) . . ?
C62 C63 H63 119.8 . . ?
C64 C63 H63 119.8 . . ?
C63 C64 C59 120.7(2) . . ?
C63 C64 H64 119.6 . . ?
C59 C64 H64 119.6 . . ?
O1 C65 O2 123.8(3) . . ?
O1 C65 C68 124.3(3) . . ?
O2 C65 C68 111.9(2) . . ?
O2 C66 C67 108.3(3) . . ?
O2 C66 H66A 110.0 . . ?
C67 C66 H66A 110.0 . . ?
O2 C66 H66B 110.0 . . ?
C67 C66 H66B 110.0 . . ?
H66A C66 H66B 108.4 . . ?
C66 C67 H67A 109.5 . . ?
C66 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C66 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C65 C68 H68A 109.5 . . ?
C65 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C65 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C70 C69 H69A 109.5 . . ?
C70 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C70 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O3 C70 C69 107.9(3) . . ?
O3 C70 H70A 110.1 . . ?
C69 C70 H70A 110.1 . . ?
O3 C70 H70B 110.1 . . ?
C69 C70 H70B 110.1 . . ?
H70A C70 H70B 108.4 . . ?
O4 C71 O3 123.4(3) . . ?
O4 C71 C72 124.3(3) . . ?
O3 C71 C72 112.3(2) . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        67.55
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_tana3_12_0m
_database_code_depnum_ccdc_archive 'CCDC 1042150'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H34 Cl2 Cu N2'
_chemical_formula_sum            'C32 H34 Cl2 Cu N2'
_chemical_formula_weight         581.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.8780(6)
_cell_length_b                   10.4574(2)
_cell_length_c                   10.7037(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.636(2)
_cell_angle_gamma                90.00
_cell_volume                     2826.44(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3219
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      67.67

_exptl_crystal_description       ?
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1212
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_T_max  0.8744
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8188
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.58
_diffrn_reflns_theta_max         66.59
_reflns_number_total             2472
_reflns_number_gt                2199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0696P)²+1.3789P] 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         2472
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_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 1.0000 -0.00501(4) 0.7500 0.04641(18) Uani 1 2 d S . .
Cl1 Cl 1.02367(3) -0.15242(6) 0.90422(7) 0.0744(2) Uani 1 1 d . . .
N1 N 0.96394(6) 0.13955(17) 0.63768(17) 0.0452(4) Uani 1 1 d . . .
H1 H 0.9838 0.1493 0.5779 0.054 Uiso 1 1 calc R . .
C1 C 0.90898(8) 0.1207(3) 0.5607(2) 0.0568(6) Uani 1 1 d . . .
H1C H 0.9070 0.0381 0.5186 0.068 Uiso 1 1 calc R . .
H1D H 0.9016 0.1857 0.4945 0.068 Uiso 1 1 calc R . .
C2 C 0.86697(8) 0.1269(2) 0.6381(2) 0.0495(5) Uani 1 1 d . . .
C3 C 0.86253(8) 0.0324(2) 0.7259(2) 0.0541(5) Uani 1 1 d . . .
H3 H 0.8874 -0.0331 0.7414 0.065 Uiso 1 1 calc R . .
C4 C 0.82187(8) 0.0334(2) 0.7911(2) 0.0524(5) Uani 1 1 d . . .
H4 H 0.8199 -0.0314 0.8494 0.063 Uiso 1 1 calc R . .
C5 C 0.78365(7) 0.1304(2) 0.7705(2) 0.0454(5) Uani 1 1 d . . .
C6 C 0.73921(7) 0.12927(19) 0.8372(2) 0.0459(5) Uani 1 1 d . . .
C7 C 0.74500(9) 0.0811(2) 0.9600(2) 0.0545(5) Uani 1 1 d . . .
H7 H 0.7774 0.0467 1.0013 0.065 Uiso 1 1 calc R . .
C8 C 0.70352(10) 0.0832(3) 1.0221(2) 0.0634(6) Uani 1 1 d . . .
H8 H 0.7082 0.0501 1.1045 0.076 Uiso 1 1 calc R . .
C9 C 0.65525(10) 0.1339(3) 0.9629(3) 0.0659(7) Uani 1 1 d . . .
H9 H 0.6275 0.1362 1.0053 0.079 Uiso 1 1 calc R . .
C10 C 0.64850(9) 0.1812(3) 0.8403(3) 0.0644(6) Uani 1 1 d . . .
H10 H 0.6159 0.2150 0.7994 0.077 Uiso 1 1 calc R . .
C11 C 0.68985(8) 0.1787(2) 0.7780(2) 0.0563(6) Uani 1 1 d . . .
H11 H 0.6847 0.2105 0.6951 0.068 Uiso 1 1 calc R . .
C12 C 0.78906(8) 0.2259(2) 0.6840(2) 0.0540(5) Uani 1 1 d . . .
H12 H 0.7646 0.2924 0.6691 0.065 Uiso 1 1 calc R . .
C13 C 0.82981(9) 0.2244(2) 0.6196(2) 0.0550(5) Uani 1 1 d . . .
H13 H 0.8324 0.2901 0.5627 0.066 Uiso 1 1 calc R . .
C14 C 0.97166(7) 0.26113(19) 0.7106(2) 0.0457(5) Uani 1 1 d . . .
H14 H 0.9476 0.2617 0.7697 0.055 Uiso 1 1 calc R . .
C15 C 0.96120(10) 0.3802(2) 0.6279(3) 0.0691(7) Uani 1 1 d . . .
H15A H 0.9839 0.3799 0.5667 0.083 Uiso 1 1 calc R . .
H15B H 0.9247 0.3802 0.5805 0.083 Uiso 1 1 calc R . .
C16 C 0.97176(12) 0.4993(2) 0.7098(4) 0.0838(10) Uani 1 1 d . . .
H16A H 0.9470 0.5033 0.7657 0.101 Uiso 1 1 calc R . .
H16B H 0.9664 0.5744 0.6552 0.101 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 2.0275(18) . ?
Cu1 N1 2.0275(18) 2_756 ?
Cu1 Cl1 2.2436(7) . ?
Cu1 Cl1 2.2436(7) 2_756 ?
N1 C14 1.482(3) . ?
N1 C1 1.493(3) . ?
N1 H1 0.9100 . ?
C1 C2 1.506(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 C3 1.385(3) . ?
C2 C13 1.386(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C5 C12 1.390(3) . ?
C5 C6 1.480(3) . ?
C6 C7 1.385(3) . ?
C6 C11 1.395(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.517(3) . ?
C14 C14 1.524(4) 2_756 ?
C14 H14 0.9800 . ?
C15 C16 1.513(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C16 1.525(6) 2_756 ?
C16 H16A 0.9700 . ?
C16 H16B 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
N1 Cu1 N1 83.57(10) . 2_756 ?
N1 Cu1 Cl1 164.74(5) . . ?
N1 Cu1 Cl1 93.43(5) 2_756 . ?
N1 Cu1 Cl1 93.43(5) . 2_756 ?
N1 Cu1 Cl1 164.74(5) 2_756 2_756 ?
Cl1 Cu1 Cl1 93.21(4) . 2_756 ?
C14 N1 C1 113.97(16) . . ?
C14 N1 Cu1 109.62(13) . . ?
C1 N1 Cu1 119.24(14) . . ?
C14 N1 H1 104.1 . . ?
C1 N1 H1 104.1 . . ?
Cu1 N1 H1 104.1 . . ?
N1 C1 C2 113.95(17) . . ?
N1 C1 H1C 108.8 . . ?
C2 C1 H1C 108.8 . . ?
N1 C1 H1D 108.8 . . ?
C2 C1 H1D 108.8 . . ?
H1C C1 H1D 107.7 . . ?
C3 C2 C13 117.6(2) . . ?
C3 C2 C1 121.3(2) . . ?
C13 C2 C1 121.0(2) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C12 C5 C4 117.0(2) . . ?
C12 C5 C6 121.94(18) . . ?
C4 C5 C6 121.0(2) . . ?
C7 C6 C11 117.7(2) . . ?
C7 C6 C5 121.75(18) . . ?
C11 C6 C5 120.6(2) . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C13 C12 C5 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C5 C12 H12 119.2 . . ?
C12 C13 C2 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C2 C13 H13 119.4 . . ?
N1 C14 C15 114.2(2) . . ?
N1 C14 C14 107.10(12) . 2_756 ?
C15 C14 C14 110.50(15) . 2_756 ?
N1 C14 H14 108.3 . . ?
C15 C14 H14 108.3 . . ?
C14 C14 H14 108.3 2_756 . ?
C16 C15 C14 110.5(3) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C16 110.9(2) . 2_756 ?
C15 C16 H16A 109.5 . . ?
C16 C16 H16A 109.5 2_756 . ?
C15 C16 H16B 109.5 . . ?
C16 C16 H16B 109.5 2_756 . ?
H16A C16 H16B 108.1 . . ?

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 C14 -14.62(9) 2_756 . . . ?
Cl1 Cu1 N1 C14 64.8(2) . . . . ?
Cl1 Cu1 N1 C14 -179.60(12) 2_756 . . . ?
N1 Cu1 N1 C1 -148.56(18) 2_756 . . . ?
Cl1 Cu1 N1 C1 -69.2(3) . . . . ?
Cl1 Cu1 N1 C1 46.47(15) 2_756 . . . ?
C14 N1 C1 C2 -56.5(3) . . . . ?
Cu1 N1 C1 C2 75.6(2) . . . . ?
N1 C1 C2 C3 -68.9(3) . . . . ?
N1 C1 C2 C13 114.2(2) . . . . ?
C13 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 -175.7(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C12 -1.1(3) . . . . ?
C3 C4 C5 C6 178.1(2) . . . . ?
C12 C5 C6 C7 -147.7(2) . . . . ?
C4 C5 C6 C7 33.2(3) . . . . ?
C12 C5 C6 C11 31.6(3) . . . . ?
C4 C5 C6 C11 -147.6(2) . . . . ?
C11 C6 C7 C8 -0.7(3) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C6 -0.4(4) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
C5 C6 C11 C10 -178.3(2) . . . . ?
C4 C5 C12 C13 0.9(3) . . . . ?
C6 C5 C12 C13 -178.2(2) . . . . ?
C5 C12 C13 C2 0.4(3) . . . . ?
C3 C2 C13 C12 -1.5(3) . . . . ?
C1 C2 C13 C12 175.6(2) . . . . ?
C1 N1 C14 C15 -60.7(2) . . . . ?
Cu1 N1 C14 C15 162.72(15) . . . . ?
C1 N1 C14 C14 176.57(19) . . . 2_756 ?
Cu1 N1 C14 C14 40.0(2) . . . 2_756 ?
N1 C14 C15 C16 -178.2(2) . . . . ?
C14 C14 C15 C16 -57.3(3) 2_756 . . . ?
C14 C15 C16 C16 56.7(4) . . . 2_756 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052
