# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1028485'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CHEMW03_3                   
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: The utility program, Squeeze, was used to remove the 
contributions to the scattering due to a disordered molecule of 
dichloromethane.  The use of Squeeze is described in the cif file.
;
_vrf_PLAT051_3                   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      54.19 %     
RESPONSE: see above
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 N4, 1/2 C H2 Cl2'
_chemical_formula_sum            'C42.50 H31 Cl N4'
_chemical_formula_weight         633.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   37.576(3)
_cell_length_b                   6.0193(4)
_cell_length_c                   30.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.952(2)
_cell_angle_gamma                90
_cell_volume                     6494.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14198
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prisms
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             2648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37888
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7387
_reflns_number_gt                5128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.001 0.000 97 20 ' '
2 0.500 0.595 0.000 97 20 ' '
3 0.500 0.452 0.500 97 20 ' '
4 1.000 0.952 0.500 97 20 ' '
_platon_squeeze_details          ?




_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'






_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0922P)²+16.0721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7387
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2212
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30323(7) 0.7292(5) 0.74743(9) 0.0258(6) Uani 1 1 d . . . . .
H1A H 0.3043 0.5664 0.7524 0.031 Uiso 1 1 calc R U . . .
H1B H 0.2779 0.7680 0.7280 0.031 Uiso 1 1 calc R U . . .
C2 C 0.31129(7) 0.8461(4) 0.79388(9) 0.0246(6) Uani 1 1 d . . . . .
C3 C 0.30114(8) 1.0665(5) 0.79626(10) 0.0306(6) Uani 1 1 d . . . . .
H3 H 0.2883 1.1446 0.7688 0.037 Uiso 1 1 calc R U . . .
C4 C 0.31001(9) 1.1714(5) 0.83921(11) 0.0356(7) Uani 1 1 d . . . . .
H4 H 0.3031 1.3218 0.8416 0.043 Uiso 1 1 calc R U . . .
C5 C 0.32898(8) 1.0541(5) 0.87846(10) 0.0337(7) Uani 1 1 d . . . . .
H5 H 0.3353 1.1215 0.9084 0.040 Uiso 1 1 calc R U . . .
C6 C 0.33865(7) 0.8344(5) 0.87315(10) 0.0300(6) Uani 1 1 d . . . . .
C7 C 0.35883(8) 0.7064(6) 0.91295(10) 0.0384(7) Uani 1 1 d . . . . .
C8 C 0.37540(9) 0.6008(6) 0.94649(11) 0.0444(8) Uani 1 1 d . . . . .
C9 C 0.39595(9) 0.4818(6) 0.98784(11) 0.0431(8) Uani 1 1 d . . . . .
C10 C 0.40212(8) 0.5795(5) 1.03118(11) 0.0391(7) Uani 1 1 d . . . . .
H10 H 0.3915 0.7204 1.0338 0.047 Uiso 1 1 calc R U . . .
C11 C 0.42370(9) 0.4725(6) 1.07076(11) 0.0431(8) Uani 1 1 d . . . . .
H11 H 0.4280 0.5413 1.1003 0.052 Uiso 1 1 calc R U . . .
C12 C 0.43895(10) 0.2682(6) 1.06757(13) 0.0521(9) Uani 1 1 d . . . . .
H12 H 0.4541 0.1975 1.0948 0.062 Uiso 1 1 calc R U . . .
C13 C 0.43221(11) 0.1648(6) 1.02460(14) 0.0551(10) Uani 1 1 d . . . . .
H13 H 0.4422 0.0216 1.0225 0.066 Uiso 1 1 calc R U . . .
C14 C 0.41079(10) 0.2714(6) 0.98470(13) 0.0516(9) Uani 1 1 d . . . . .
H14 H 0.4062 0.2011 0.9552 0.062 Uiso 1 1 calc R U . . .
C15 C 0.36695(7) 0.6956(5) 0.74619(9) 0.0275(6) Uani 1 1 d . . . . .
H15A H 0.3666 0.5367 0.7375 0.033 Uiso 1 1 calc R U . . .
H15B H 0.3718 0.7043 0.7804 0.033 Uiso 1 1 calc R U . . .
C16 C 0.39784(7) 0.8115(5) 0.73275(9) 0.0251(6) Uani 1 1 d . . . . .
C17 C 0.40285(8) 1.0386(5) 0.73918(9) 0.0297(6) Uani 1 1 d . . . . .
H17 H 0.3858 1.1243 0.7499 0.036 Uiso 1 1 calc R U . . .
C18 C 0.43285(8) 1.1389(5) 0.72981(10) 0.0327(6) Uani 1 1 d . . . . .
H18 H 0.4370 1.2940 0.7343 0.039 Uiso 1 1 calc R U . . .
C19 C 0.45675(7) 1.0086(5) 0.71365(9) 0.0282(6) Uani 1 1 d . . . . .
H19 H 0.4777 1.0732 0.7070 0.034 Uiso 1 1 calc R U . . .
C20 C 0.44987(7) 0.7843(5) 0.70722(8) 0.0251(6) Uani 1 1 d . . . . .
C21 C 0.47442(7) 0.6456(5) 0.69037(9) 0.0274(6) Uani 1 1 d . . . . .
C22 C 0.49569(7) 0.5393(5) 0.67576(9) 0.0286(6) Uani 1 1 d . . . . .
C23 C 0.52084(7) 0.4065(5) 0.65877(9) 0.0277(6) Uani 1 1 d . . . . .
C24 C 0.55716(7) 0.4788(5) 0.66408(10) 0.0316(6) Uani 1 1 d . . . . .
H24 H 0.5650 0.6196 0.6778 0.038 Uiso 1 1 calc R U . . .
C25 C 0.58172(8) 0.3474(5) 0.64960(11) 0.0365(7) Uani 1 1 d . . . . .
H25 H 0.6063 0.3980 0.6531 0.044 Uiso 1 1 calc R U . . .
C26 C 0.57051(9) 0.1426(6) 0.63001(11) 0.0409(8) Uani 1 1 d . . . . .
H26 H 0.5878 0.0496 0.6213 0.049 Uiso 1 1 calc R U . . .
C27 C 0.53439(10) 0.0718(6) 0.62299(12) 0.0425(8) Uani 1 1 d . . . . .
H27 H 0.5266 -0.0671 0.6084 0.051 Uiso 1 1 calc R U . . .
C28 C 0.50943(8) 0.2029(5) 0.63725(11) 0.0366(7) Uani 1 1 d . . . . .
H28 H 0.4845 0.1540 0.6324 0.044 Uiso 1 1 calc R U . . .
C29 C 0.31825(7) 0.7234(5) 0.67449(9) 0.0264(6) Uani 1 1 d . . . . .
H29A H 0.3115 0.5641 0.6733 0.032 Uiso 1 1 calc R U . . .
H29B H 0.3394 0.7388 0.6613 0.032 Uiso 1 1 calc R U . . .
C30 C 0.28552(7) 0.8523(4) 0.64425(9) 0.0245(6) Uani 1 1 d . . . . .
C31 C 0.27858(7) 1.0729(4) 0.65323(9) 0.0275(6) Uani 1 1 d . . . . .
H31 H 0.2935 1.1463 0.6802 0.033 Uiso 1 1 calc R U . . .
C32 C 0.24952(8) 1.1824(5) 0.62204(10) 0.0302(6) Uani 1 1 d . . . . .
H32 H 0.2442 1.3328 0.6272 0.036 Uiso 1 1 calc R U . . .
C33 C 0.22833(8) 1.0700(5) 0.58315(9) 0.0296(6) Uani 1 1 d . . . . .
H33 H 0.2082 1.1416 0.5612 0.035 Uiso 1 1 calc R U . . .
C34 C 0.23709(7) 0.8503(5) 0.57691(9) 0.0264(6) Uani 1 1 d . . . . .
C35 C 0.21625(8) 0.7238(5) 0.53715(10) 0.0311(6) Uani 1 1 d . . . . .
C36 C 0.19966(8) 0.6158(5) 0.50409(10) 0.0325(6) Uani 1 1 d . . . . .
C37 C 0.18010(8) 0.4881(5) 0.46407(9) 0.0309(6) Uani 1 1 d . . . . .
C38 C 0.19271(8) 0.2789(5) 0.45627(9) 0.0312(6) Uani 1 1 d . . . . .
H38 H 0.2144 0.2190 0.4778 0.037 Uiso 1 1 calc R U . . .
C39 C 0.17396(8) 0.1570(5) 0.41743(10) 0.0343(7) Uani 1 1 d . . . . .
H39 H 0.1826 0.0135 0.4124 0.041 Uiso 1 1 calc R U . . .
C40 C 0.14239(8) 0.2452(5) 0.38575(10) 0.0351(7) Uani 1 1 d . . . . .
H40 H 0.1296 0.1627 0.3589 0.042 Uiso 1 1 calc R U . . .
C41 C 0.12977(8) 0.4513(5) 0.39339(10) 0.0366(7) Uani 1 1 d . . . . .
H41 H 0.1080 0.5103 0.3719 0.044 Uiso 1 1 calc R U . . .
C42 C 0.14841(8) 0.5744(5) 0.43220(10) 0.0345(7) Uani 1 1 d . . . . .
H42 H 0.1396 0.7176 0.4371 0.041 Uiso 1 1 calc R U . . .
N1 N 0.33037(6) 0.7940(4) 0.72330(7) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.32975(6) 0.7303(4) 0.83143(8) 0.0269(5) Uani 1 1 d . . . . .
N3 N 0.42050(6) 0.6838(4) 0.71647(7) 0.0252(5) Uani 1 1 d . . . . .
N4 N 0.26516(6) 0.7413(4) 0.60715(7) 0.0267(5) Uani 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 1.465(3) . ?
C1 C2 1.512(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.335(3) . ?
C2 C3 1.388(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C6 N2 1.352(3) . ?
C6 C7 1.438(4) . ?
C7 C8 1.200(4) . ?
C8 C9 1.446(4) . ?
C9 C10 1.384(4) . ?
C9 C14 1.398(5) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.470(3) . ?
C15 C16 1.507(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.341(3) . ?
C16 C17 1.386(4) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(4) . ?
C19 H19 0.9500 . ?
C20 N3 1.357(3) . ?
C20 C21 1.441(4) . ?
C21 C22 1.202(4) . ?
C22 C23 1.440(4) . ?
C23 C28 1.393(4) . ?
C23 C24 1.397(4) . ?
C24 C25 1.379(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.379(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N1 1.465(3) . ?
C29 C30 1.512(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 N4 1.332(3) . ?
C30 C31 1.395(4) . ?
C31 C32 1.381(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.383(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(4) . ?
C33 H33 0.9500 . ?
C34 N4 1.345(3) . ?
C34 C35 1.440(4) . ?
C35 C36 1.198(4) . ?
C36 C37 1.435(4) . ?
C37 C38 1.389(4) . ?
C37 C42 1.392(4) . ?
C38 C39 1.384(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.371(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.386(4) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.5(2) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C3 122.6(3) . . ?
N2 C2 C1 116.8(2) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N2 C6 C5 122.9(3) . . ?
N2 C6 C7 116.7(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C6 179.2(4) . . ?
C7 C8 C9 177.7(4) . . ?
C10 C9 C14 119.2(3) . . ?
C10 C9 C8 119.8(3) . . ?
C14 C9 C8 121.0(3) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N1 C15 C16 112.1(2) . . ?
N1 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N3 C16 C17 122.8(3) . . ?
N3 C16 C15 116.9(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N3 C20 C19 122.6(2) . . ?
N3 C20 C21 117.1(2) . . ?
C19 C20 C21 120.3(3) . . ?
C22 C21 C20 176.7(3) . . ?
C21 C22 C23 178.4(3) . . ?
C28 C23 C24 119.0(3) . . ?
C28 C23 C22 120.5(3) . . ?
C24 C23 C22 120.5(3) . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 120.1(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
N1 C29 C30 114.4(2) . . ?
N1 C29 H29A 108.7 . . ?
C30 C29 H29A 108.7 . . ?
N1 C29 H29B 108.7 . . ?
C30 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
N4 C30 C31 123.0(2) . . ?
N4 C30 C29 114.4(2) . . ?
C31 C30 C29 122.5(2) . . ?
C32 C31 C30 118.6(2) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C31 C32 C33 119.0(3) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C34 118.6(2) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
N4 C34 C33 122.9(2) . . ?
N4 C34 C35 115.6(2) . . ?
C33 C34 C35 121.5(2) . . ?
C36 C35 C34 178.5(3) . . ?
C35 C36 C37 179.1(3) . . ?
C38 C37 C42 119.2(3) . . ?
C38 C37 C36 120.7(3) . . ?
C42 C37 C36 120.1(3) . . ?
C39 C38 C37 120.5(3) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 119.8(3) . . ?
C38 C39 H39 120.1 . . ?
C40 C39 H39 120.1 . . ?
C41 C40 C39 119.9(3) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C40 C41 C42 120.6(3) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C37 120.0(3) . . ?
C41 C42 H42 120.0 . . ?
C37 C42 H42 120.0 . . ?
C29 N1 C1 111.0(2) . . ?
C29 N1 C15 109.0(2) . . ?
C1 N1 C15 110.6(2) . . ?
C2 N2 C6 117.9(2) . . ?
C16 N3 C20 117.4(2) . . ?
C30 N4 C34 117.8(2) . . ?

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 N2 -99.2(3) . . . . ?
N1 C1 C2 C3 78.1(3) . . . . ?
N2 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 -177.9(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 N2 -1.1(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C14 C9 C10 C11 1.9(5) . . . . ?
C8 C9 C10 C11 -176.1(3) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 -1.3(6) . . . . ?
C11 C12 C13 C14 1.7(6) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C10 C9 C14 C13 -1.6(6) . . . . ?
C8 C9 C14 C13 176.4(4) . . . . ?
N1 C15 C16 N3 -127.0(2) . . . . ?
N1 C15 C16 C17 55.7(3) . . . . ?
N3 C16 C17 C18 -1.8(4) . . . . ?
C15 C16 C17 C18 175.4(2) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 N3 -0.5(4) . . . . ?
C18 C19 C20 C21 180.0(2) . . . . ?
C28 C23 C24 C25 -2.1(4) . . . . ?
C22 C23 C24 C25 177.2(3) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C24 C25 C26 C27 2.7(5) . . . . ?
C25 C26 C27 C28 -2.5(5) . . . . ?
C26 C27 C28 C23 -0.1(5) . . . . ?
C24 C23 C28 C27 2.3(4) . . . . ?
C22 C23 C28 C27 -177.0(3) . . . . ?
N1 C29 C30 N4 -154.1(2) . . . . ?
N1 C29 C30 C31 29.2(4) . . . . ?
N4 C30 C31 C32 -0.7(4) . . . . ?
C29 C30 C31 C32 175.7(3) . . . . ?
C30 C31 C32 C33 0.1(4) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C32 C33 C34 N4 0.4(4) . . . . ?
C32 C33 C34 C35 -179.8(3) . . . . ?
C42 C37 C38 C39 -0.3(4) . . . . ?
C36 C37 C38 C39 -179.5(3) . . . . ?
C37 C38 C39 C40 0.5(4) . . . . ?
C38 C39 C40 C41 -0.7(5) . . . . ?
C39 C40 C41 C42 0.7(5) . . . . ?
C40 C41 C42 C37 -0.5(5) . . . . ?
C38 C37 C42 C41 0.3(4) . . . . ?
C36 C37 C42 C41 179.5(3) . . . . ?
C30 C29 N1 C1 71.0(3) . . . . ?
C30 C29 N1 C15 -166.8(2) . . . . ?
C2 C1 N1 C29 -167.1(2) . . . . ?
C2 C1 N1 C15 71.7(3) . . . . ?
C16 C15 N1 C29 75.6(3) . . . . ?
C16 C15 N1 C1 -162.0(2) . . . . ?
C3 C2 N2 C6 0.1(4) . . . . ?
C1 C2 N2 C6 177.3(2) . . . . ?
C5 C6 N2 C2 0.9(4) . . . . ?
C7 C6 N2 C2 -179.4(2) . . . . ?
C17 C16 N3 C20 1.6(4) . . . . ?
C15 C16 N3 C20 -175.7(2) . . . . ?
C19 C20 N3 C16 -0.4(4) . . . . ?
C21 C20 N3 C16 179.1(2) . . . . ?
C31 C30 N4 C34 1.1(4) . . . . ?
C29 C30 N4 C34 -175.6(2) . . . . ?
C33 C34 N4 C30 -0.9(4) . . . . ?
C35 C34 N4 C30 179.3(2) . . . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1028486'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N4'
_chemical_formula_sum            'C26 H22 N4'
_chemical_formula_weight         390.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   23.3542(19)
_cell_length_b                   6.1583(6)
_cell_length_c                   29.500(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.130(6)
_cell_angle_gamma                90
_cell_volume                     4231.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3997
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      20.6

_exptl_crystal_description       laths
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. Apex II release 2010, Bruker AXS, Inc.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42921
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.422
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4834
_reflns_number_gt                2901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1069P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4834
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32318(9) 0.1512(4) 0.03844(8) 0.0298(5) Uani 1 1 d . . . . .
C2 C 0.27446(9) 0.2647(4) 0.05881(7) 0.0296(5) Uani 1 1 d . . . . .
C3 C 0.26892(11) 0.4900(4) 0.05627(9) 0.0360(6) Uani 1 1 d . . . . .
C4 C 0.22317(11) 0.5898(4) 0.07467(9) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.18420(11) 0.4640(5) 0.09549(9) 0.0432(6) Uani 1 1 d . . . . .
C6 C 0.19285(11) 0.2428(4) 0.09719(9) 0.0430(6) Uani 1 1 d . . . . .
C7 C 0.42589(10) 0.1357(4) 0.03615(8) 0.0285(5) Uani 1 1 d . . . . .
C8 C 0.43222(9) 0.2747(3) -0.00513(7) 0.0269(5) Uani 1 1 d . . . . .
C9 C 0.42178(10) 0.4970(4) -0.00456(8) 0.0302(5) Uani 1 1 d . . . . .
C10 C 0.43042(10) 0.6189(4) -0.04276(8) 0.0321(5) Uani 1 1 d . . . . .
C11 C 0.44949(10) 0.5157(4) -0.08017(8) 0.0331(5) Uani 1 1 d . . . . .
C12 C 0.45929(10) 0.2949(4) -0.07807(8) 0.0331(5) Uani 1 1 d . . . . .
C13 C 0.38351(10) 0.1043(4) 0.10766(8) 0.0306(5) Uani 1 1 d . . . . .
C14 C 0.42890(9) 0.2133(4) 0.13864(7) 0.0275(5) Uani 1 1 d . . . . .
C15 C 0.42458(10) 0.4335(4) 0.14790(8) 0.0314(5) Uani 1 1 d . . . . .
C16 C 0.46571(10) 0.5319(4) 0.17739(8) 0.0324(5) Uani 1 1 d . . . . .
C17 C 0.50974(10) 0.4034(4) 0.19648(8) 0.0330(5) Uani 1 1 d . . . . .
C18 C 0.51115(9) 0.1840(4) 0.18551(7) 0.0285(5) Uani 1 1 d . . . . .
C19 C 0.55647(10) 0.0479(4) 0.20520(8) 0.0335(5) Uani 1 1 d . . . . .
C20 C 0.59444(10) -0.0609(4) 0.22338(8) 0.0352(6) Uani 1 1 d . . . . .
C21 C 0.63752(9) -0.1895(4) 0.24778(8) 0.0323(5) Uani 1 1 d . . . . .
C22 C 0.66191(10) -0.1162(4) 0.28971(8) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.70092(11) -0.2426(5) 0.31537(9) 0.0435(6) Uani 1 1 d . . . . .
C24 C 0.71667(12) -0.4421(5) 0.29957(10) 0.0478(7) Uani 1 1 d . . . . .
C25 C 0.69424(11) -0.5160(5) 0.25805(10) 0.0477(7) Uani 1 1 d . . . . .
C26 C 0.65476(12) -0.3901(4) 0.23170(10) 0.0418(6) Uani 1 1 d . . . . .
N1 N 0.37853(7) 0.2051(3) 0.06257(6) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.23691(8) 0.1415(3) 0.07932(7) 0.0361(5) Uani 1 1 d . . . . .
N3 N 0.45065(8) 0.1731(3) -0.04142(6) 0.0310(5) Uani 1 1 d . . . . .
N4 N 0.47133(8) 0.0877(3) 0.15669(6) 0.0280(4) Uani 1 1 d . . . . .
H1A H 0.3154(9) -0.011(4) 0.0379(7) 0.027(6) Uiso 1 1 d . . . . .
H1B H 0.3259(9) 0.198(3) 0.0077(8) 0.029(6) Uiso 1 1 d . . . . .
H3 H 0.2965(11) 0.573(4) 0.0395(9) 0.043(7) Uiso 1 1 d . . . . .
H4 H 0.2193(10) 0.742(4) 0.0723(8) 0.033(6) Uiso 1 1 d . . . . .
H5 H 0.1539(11) 0.529(4) 0.1121(8) 0.042(7) Uiso 1 1 d . . . . .
H6 H 0.1661(13) 0.146(4) 0.1143(10) 0.057(8) Uiso 1 1 d . . . . .
H9 H 0.4079(10) 0.568(4) 0.0223(8) 0.034(6) Uiso 1 1 d . . . . .
H10 H 0.4249(10) 0.772(4) -0.0410(8) 0.032(6) Uiso 1 1 d . . . . .
H11 H 0.4561(10) 0.593(4) -0.1061(9) 0.032(6) Uiso 1 1 d . . . . .
H12 H 0.4751(10) 0.218(4) -0.1034(8) 0.034(6) Uiso 1 1 d . . . . .
H13A H 0.3916(10) -0.053(4) 0.1061(8) 0.031(6) Uiso 1 1 d . . . . .
H13B H 0.3453(11) 0.131(3) 0.1208(8) 0.036(6) Uiso 1 1 d . . . . .
H15 H 0.3936(11) 0.518(4) 0.1334(9) 0.042(7) Uiso 1 1 d . . . . .
H16 H 0.4638(10) 0.697(4) 0.1843(8) 0.035(6) Uiso 1 1 d . . . . .
H22 H 0.6498(10) 0.025(4) 0.3007(8) 0.037(7) Uiso 1 1 d . . . . .
H23 H 0.7191(13) -0.186(4) 0.3467(12) 0.068(9) Uiso 1 1 d . . . . .
H24 H 0.7457(13) -0.532(5) 0.3201(10) 0.065(9) Uiso 1 1 d . . . . .
H25 H 0.7038(13) -0.660(5) 0.2452(10) 0.060(9) Uiso 1 1 d . . . . .
H26 H 0.6404(12) -0.437(4) 0.2030(10) 0.054(8) Uiso 1 1 d . . . . .
H7A H 0.4228(9) -0.020(4) 0.0264(7) 0.030(6) Uiso 1 1 d . . . . .
H17 H 0.5383(12) 0.462(4) 0.2170(9) 0.045(7) Uiso 1 1 d . . . . .
H7B H 0.4617(11) 0.149(3) 0.0562(8) 0.033(6) 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 1.468(3) . ?
C1 C2 1.498(3) . ?
C1 H1A 1.02(2) . ?
C1 H1B 0.96(2) . ?
C2 N2 1.337(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.378(4) . ?
C3 H3 0.98(3) . ?
C4 C5 1.373(4) . ?
C4 H4 0.94(2) . ?
C5 C6 1.377(4) . ?
C5 H5 0.98(2) . ?
C6 N2 1.343(3) . ?
C6 H6 1.02(3) . ?
C7 N1 1.462(3) . ?
C7 C8 1.504(3) . ?
C7 H7A 1.00(2) . ?
C7 H7B 0.99(3) . ?
C8 N3 1.337(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.98(2) . ?
C10 C11 1.375(3) . ?
C10 H10 0.96(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.92(2) . ?
C12 N3 1.343(3) . ?
C12 H12 0.98(2) . ?
C13 N1 1.465(3) . ?
C13 C14 1.507(3) . ?
C13 H13A 0.99(2) . ?
C13 H13B 1.01(2) . ?
C14 N4 1.337(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.97(3) . ?
C16 C17 1.385(3) . ?
C16 H16 1.04(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.94(3) . ?
C18 N4 1.351(3) . ?
C18 C19 1.439(3) . ?
C19 C20 1.206(3) . ?
C20 C21 1.433(3) . ?
C21 C26 1.393(3) . ?
C21 C22 1.399(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.98(2) . ?
C23 C24 1.373(4) . ?
C23 H23 1.05(3) . ?
C24 C25 1.374(4) . ?
C24 H24 1.03(3) . ?
C25 C26 1.397(4) . ?
C25 H25 1.00(3) . ?
C26 H26 0.94(3) . ?

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 111.58(18) . . ?
N1 C1 H1A 112.3(13) . . ?
C2 C1 H1A 109.1(11) . . ?
N1 C1 H1B 105.9(14) . . ?
C2 C1 H1B 110.1(13) . . ?
H1A C1 H1B 107.8(17) . . ?
N2 C2 C3 121.8(2) . . ?
N2 C2 C1 117.3(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 121.3(14) . . ?
C2 C3 H3 119.0(14) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 122.0(14) . . ?
C3 C4 H4 119.2(14) . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 H5 121.5(15) . . ?
C6 C5 H5 119.8(15) . . ?
N2 C6 C5 124.0(2) . . ?
N2 C6 H6 115.8(15) . . ?
C5 C6 H6 120.0(15) . . ?
N1 C7 C8 112.80(18) . . ?
N1 C7 H7A 113.0(12) . . ?
C8 C7 H7A 108.8(12) . . ?
N1 C7 H7B 107.1(13) . . ?
C8 C7 H7B 107.9(13) . . ?
H7A C7 H7B 106.9(18) . . ?
N3 C8 C9 122.5(2) . . ?
N3 C8 C7 115.97(19) . . ?
C9 C8 C7 121.51(19) . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 119.5(14) . . ?
C8 C9 H9 121.2(14) . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 123.7(13) . . ?
C9 C10 H10 117.7(14) . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 120.5(14) . . ?
C12 C11 H11 120.7(14) . . ?
N3 C12 C11 123.5(2) . . ?
N3 C12 H12 115.6(13) . . ?
C11 C12 H12 120.8(13) . . ?
N1 C13 C14 111.64(18) . . ?
N1 C13 H13A 112.1(13) . . ?
C14 C13 H13A 109.6(14) . . ?
N1 C13 H13B 105.4(14) . . ?
C14 C13 H13B 107.3(14) . . ?
H13A C13 H13B 110.6(18) . . ?
N4 C14 C15 123.3(2) . . ?
N4 C14 C13 116.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.0(15) . . ?
C16 C15 H15 120.5(15) . . ?
C17 C16 C15 117.7(2) . . ?
C17 C16 H16 121.3(14) . . ?
C15 C16 H16 120.9(14) . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 121.0(16) . . ?
C18 C17 H17 119.6(16) . . ?
N4 C18 C17 123.1(2) . . ?
N4 C18 C19 116.8(2) . . ?
C17 C18 C19 120.1(2) . . ?
C20 C19 C18 177.2(3) . . ?
C19 C20 C21 176.1(2) . . ?
C26 C21 C22 118.6(2) . . ?
C26 C21 C20 121.9(2) . . ?
C22 C21 C20 119.5(2) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 120.9(15) . . ?
C21 C22 H22 118.2(14) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 119.8(16) . . ?
C22 C23 H23 120.2(16) . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 117.2(16) . . ?
C25 C24 H24 122.5(16) . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 123.5(18) . . ?
C26 C25 H25 116.1(18) . . ?
C21 C26 C25 119.9(3) . . ?
C21 C26 H26 119.4(17) . . ?
C25 C26 H26 120.7(17) . . ?
C7 N1 C13 110.29(18) . . ?
C7 N1 C1 110.42(17) . . ?
C13 N1 C1 110.75(17) . . ?
C2 N2 C6 117.4(2) . . ?
C8 N3 C12 117.32(19) . . ?
C14 N4 C18 116.99(19) . . ?

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 N2 -113.0(2) . . . . ?
N1 C1 C2 C3 67.0(3) . . . . ?
N2 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 N2 -0.6(4) . . . . ?
N1 C7 C8 N3 -146.75(19) . . . . ?
N1 C7 C8 C9 35.9(3) . . . . ?
N3 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 N3 0.7(4) . . . . ?
N1 C13 C14 N4 -122.7(2) . . . . ?
N1 C13 C14 C15 58.6(3) . . . . ?
N4 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 C15 C16 178.3(2) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 N4 0.1(3) . . . . ?
C16 C17 C18 C19 -179.7(2) . . . . ?
C26 C21 C22 C23 -2.0(3) . . . . ?
C20 C21 C22 C23 175.9(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C22 C21 C26 C25 2.0(4) . . . . ?
C20 C21 C26 C25 -175.9(2) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C8 C7 N1 C13 -165.12(18) . . . . ?
C8 C7 N1 C1 72.1(2) . . . . ?
C14 C13 N1 C7 76.7(2) . . . . ?
C14 C13 N1 C1 -160.77(19) . . . . ?
C2 C1 N1 C7 -166.60(18) . . . . ?
C2 C1 N1 C13 70.9(2) . . . . ?
C3 C2 N2 C6 0.7(3) . . . . ?
C1 C2 N2 C6 -179.3(2) . . . . ?
C5 C6 N2 C2 0.2(4) . . . . ?
C9 C8 N3 C12 0.3(3) . . . . ?
C7 C8 N3 C12 -176.96(19) . . . . ?
C11 C12 N3 C8 -0.8(3) . . . . ?
C15 C14 N4 C18 0.5(3) . . . . ?
C13 C14 N4 C18 -178.14(18) . . . . ?
C17 C18 N4 C14 -0.4(3) . . . . ?
C19 C18 N4 C14 179.45(18) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1028487'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT019_2                   
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.979 Report
RESPONSE: A complete data set out to 50 degrees in 2 theta was 
collected.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 N4'
_chemical_formula_sum            'C34 H26 N4'
_chemical_formula_weight         490.59

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1075(12)
_cell_length_b                   18.770(3)
_cell_length_c                   24.794(4)
_cell_angle_alpha                108.838(6)
_cell_angle_beta                 90.297(6)
_cell_angle_gamma                98.256(6)
_cell_volume                     2658.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2090
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      20.4

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. Apex II release 2010, Bruker AXS, Inc.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24454
_diffrn_reflns_av_unetI/netI     0.2126
_diffrn_reflns_av_R_equivalents  0.1166
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         25.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             9316
_reflns_number_gt                4022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
There are two crystallographically unique molecules in the asymmetric unit.  In 
one, there is disordered phenyl ring.  The disorder model included one of the 
acetylenic carbon atoms.  The disorder was modeled by assigning the variable x 
to the site occupancy factors for one component of the disorder.  The variable 
(1-x) was assigned to the site occupancy factors for the alternate component.  
A common isotropic displacement parameter was refined for the atoms of the two 
components while refining x.  In this way, the site occupancy for the major 
component consisting of atoms C7, C8, C9, C10, C11, C12 and C13 refined to 
77(2)%.  The geometry of the two components was restrained to be equivalent 
throughout the refinement process.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0091(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9316
_refine_ls_number_parameters     707
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.022
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1390(7) -0.1856(2) 0.26578(16) 0.0253(11) Uani 1 1 d . . . . .
C2 C -0.0877(7) -0.2077(2) 0.26466(18) 0.0326(11) Uani 1 1 d . . . . .
H2 H -0.1568 -0.2080 0.2988 0.039 Uiso 1 1 calc R U . . .
C3 C -0.2127(7) -0.2290(2) 0.21433(19) 0.0377(12) Uani 1 1 d . . . . .
H3 H -0.3680 -0.2451 0.2131 0.045 Uiso 1 1 calc R U . . .
C4 C -0.1081(7) -0.2267(2) 0.16542(18) 0.0322(11) Uani 1 1 d . . . . .
H4 H -0.1902 -0.2409 0.1299 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1197(7) -0.2031(2) 0.16924(18) 0.0303(11) Uani 1 1 d . . . . .
C6 C 0.2340(7) -0.1970(2) 0.11975(18) 0.0387(12) Uani 1 1 d . . . . .
C7 C 0.3315(10) -0.1932(3) 0.0775(3) 0.0339(17) Uani 0.766 1 d D U P A 1
C8 C 0.4284(9) -0.1824(2) 0.0277(2) 0.0343(13) Uani 0.766 1 d D U P A 1
C9 C 0.6446(9) -0.1480(3) 0.0295(2) 0.0481(16) Uani 0.766 1 d D U P A 1
H9 H 0.7321 -0.1318 0.0643 0.058 Uiso 0.766 1 calc R U P A 1
C10 C 0.7365(10) -0.1368(3) -0.0184(2) 0.0541(16) Uani 0.766 1 d D U P A 1
H10 H 0.8861 -0.1133 -0.0165 0.065 Uiso 0.766 1 calc R U P A 1
C11 C 0.6099(9) -0.1600(3) -0.0692(2) 0.0444(15) Uani 0.766 1 d D U P A 1
H11 H 0.6716 -0.1518 -0.1022 0.053 Uiso 0.766 1 calc R U P A 1
C12 C 0.3917(13) -0.1953(4) -0.0717(3) 0.0470(15) Uani 0.766 1 d D U P A 1
H12 H 0.3049 -0.2118 -0.1067 0.056 Uiso 0.766 1 calc R U P A 1
C13 C 0.3006(12) -0.2063(3) -0.0234(2) 0.0375(15) Uani 0.766 1 d D U P A 1
H13 H 0.1514 -0.2301 -0.0251 0.045 Uiso 0.766 1 calc R U P A 1
C7A C 0.278(3) -0.1719(12) 0.0816(8) 0.032 Uiso 0.234 1 d D U P A 2
C8A C 0.361(2) -0.1507(8) 0.0341(6) 0.034 Uiso 0.234 1 d D U P A 2
C9A C 0.470(2) -0.0785(8) 0.0412(6) 0.046 Uiso 0.234 1 d D U P A 2
H9A H 0.4909 -0.0422 0.0785 0.055 Uiso 0.234 1 calc R U P A 2
C10A C 0.550(2) -0.0574(8) -0.0042(6) 0.053 Uiso 0.234 1 d D U P A 2
H10A H 0.6251 -0.0074 0.0015 0.064 Uiso 0.234 1 calc R U P A 2
C11A C 0.518(3) -0.1108(10) -0.0585(6) 0.053 Uiso 0.234 1 d D U P A 2
H11A H 0.5722 -0.0974 -0.0903 0.063 Uiso 0.234 1 calc R U P A 2
C12A C 0.409(4) -0.1839(10) -0.0666(7) 0.044 Uiso 0.234 1 d D U P A 2
H12A H 0.3878 -0.2201 -0.1039 0.053 Uiso 0.234 1 calc R U P A 2
C13A C 0.329(3) -0.2044(10) -0.0204(7) 0.037 Uiso 0.234 1 d D U P A 2
H13A H 0.2541 -0.2544 -0.0260 0.044 Uiso 0.234 1 calc R U P A 2
C14 C 0.2765(6) -0.1573(2) 0.32087(16) 0.0259(11) Uani 1 1 d . . . . .
H14A H 0.2201 -0.1869 0.3459 0.031 Uiso 1 1 calc R U . . .
H14B H 0.4317 -0.1651 0.3132 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4002(6) -0.0285(2) 0.32142(16) 0.0232(10) Uani 1 1 d . . . . .
H15A H 0.3913 -0.0560 0.2798 0.028 Uiso 1 1 calc R U . . .
H15B H 0.5575 -0.0191 0.3352 0.028 Uiso 1 1 calc R U . . .
C16 C 0.3185(6) 0.0462(2) 0.33230(15) 0.0200(10) Uani 1 1 d . . . . .
C17 C 0.0973(7) 0.0480(2) 0.32065(15) 0.0248(11) Uani 1 1 d . . . . .
H17 H -0.0053 0.0021 0.3081 0.030 Uiso 1 1 calc R U . . .
C18 C 0.0273(6) 0.1172(2) 0.32744(15) 0.0242(10) Uani 1 1 d . . . . .
H18 H -0.1232 0.1198 0.3195 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1826(6) 0.1826(2) 0.34606(15) 0.0230(10) Uani 1 1 d . . . . .
H19 H 0.1402 0.2310 0.3512 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3995(6) 0.1767(2) 0.35713(15) 0.0206(10) Uani 1 1 d . . . . .
C21 C 0.5649(7) 0.2442(2) 0.37712(15) 0.0244(10) Uani 1 1 d . . . . .
C22 C 0.6996(7) 0.3011(2) 0.39260(15) 0.0235(10) Uani 1 1 d . . . . .
C23 C 0.8624(6) 0.3686(2) 0.41071(15) 0.0211(10) Uani 1 1 d . . . . .
C24 C 1.0684(7) 0.3690(2) 0.43482(15) 0.0295(11) Uani 1 1 d . . . . .
H24 H 1.1008 0.3246 0.4417 0.035 Uiso 1 1 calc R U . . .
C25 C 1.2266(7) 0.4334(3) 0.44883(17) 0.0337(11) Uani 1 1 d . . . . .
H25 H 1.3682 0.4328 0.4645 0.040 Uiso 1 1 calc R U . . .
C26 C 1.1800(7) 0.4987(2) 0.44011(16) 0.0346(12) Uani 1 1 d . . . . .
H26 H 1.2896 0.5427 0.4495 0.042 Uiso 1 1 calc R U . . .
C27 C 0.9737(7) 0.4999(2) 0.41774(16) 0.0324(11) Uani 1 1 d . . . . .
H27 H 0.9396 0.5453 0.4128 0.039 Uiso 1 1 calc R U . . .
C28 C 0.8172(6) 0.4351(2) 0.40259(15) 0.0237(10) Uani 1 1 d . . . . .
H28 H 0.6766 0.4359 0.3864 0.028 Uiso 1 1 calc R U . . .
C29 C 0.3494(6) -0.0523(2) 0.41027(15) 0.0226(10) Uani 1 1 d . . . . .
H29A H 0.3756 0.0041 0.4256 0.027 Uiso 1 1 calc R U . . .
H29B H 0.4934 -0.0700 0.4122 0.027 Uiso 1 1 calc R U . . .
C30 C 0.1942(6) -0.0818(2) 0.44799(16) 0.0208(10) Uani 1 1 d . . . . .
C31 C -0.0339(6) -0.0945(2) 0.43695(16) 0.0277(11) Uani 1 1 d . . . . .
H31 H -0.0962 -0.0877 0.4041 0.033 Uiso 1 1 calc R U . . .
C32 C -0.1692(7) -0.1176(2) 0.47533(17) 0.0317(11) Uani 1 1 d . . . . .
H32 H -0.3259 -0.1268 0.4693 0.038 Uiso 1 1 calc R U . . .
C33 C -0.0696(7) -0.1268(2) 0.52246(16) 0.0274(11) Uani 1 1 d . . . . .
H33 H -0.1569 -0.1429 0.5492 0.033 Uiso 1 1 calc R U . . .
C34 C 0.1553(7) -0.1125(2) 0.52983(16) 0.0276(11) Uani 1 1 d . . . . .
H34 H 0.2212 -0.1178 0.5629 0.033 Uiso 1 1 calc R U . . .
C35 C 0.4251(7) 0.4173(3) 0.27756(18) 0.0320(11) Uani 1 1 d . . . . .
C36 C 0.1973(7) 0.4129(3) 0.28317(17) 0.0337(11) Uani 1 1 d . . . . .
H36 H 0.1308 0.4578 0.2952 0.040 Uiso 1 1 calc R U . . .
C37 C 0.0710(7) 0.3429(3) 0.27112(16) 0.0297(11) Uani 1 1 d . . . . .
H37 H -0.0845 0.3382 0.2753 0.036 Uiso 1 1 calc R U . . .
C38 C 0.1742(7) 0.2787(2) 0.25270(15) 0.0262(11) Uani 1 1 d . . . . .
H38 H 0.0905 0.2294 0.2450 0.031 Uiso 1 1 calc R U . . .
C39 C 0.3998(7) 0.2870(2) 0.24562(15) 0.0230(10) Uani 1 1 d . . . . .
C40 C 0.5109(7) 0.2218(3) 0.22581(16) 0.0262(11) Uani 1 1 d . . . . .
C41 C 0.5934(7) 0.1657(3) 0.20906(16) 0.0264(11) Uani 1 1 d . . . . .
C42 C 0.6995(7) 0.0978(2) 0.19095(15) 0.0248(10) Uani 1 1 d . . . . .
C43 C 0.8954(7) 0.0971(3) 0.16208(17) 0.0374(12) Uani 1 1 d . . . . .
H43 H 0.9552 0.1403 0.1520 0.045 Uiso 1 1 calc R U . . .
C44 C 1.0025(8) 0.0347(3) 0.14813(19) 0.0471(14) Uani 1 1 d . . . . .
H44 H 1.1357 0.0350 0.1286 0.057 Uiso 1 1 calc R U . . .
C45 C 0.9162(8) -0.0291(3) 0.16258(18) 0.0427(13) Uani 1 1 d . . . . .
H45 H 0.9929 -0.0717 0.1543 0.051 Uiso 1 1 calc R U . . .
C46 C 0.7164(8) -0.0299(3) 0.18936(17) 0.0369(12) Uani 1 1 d . . . . .
H46 H 0.6533 -0.0741 0.1979 0.044 Uiso 1 1 calc R U . . .
C47 C 0.6097(7) 0.0331(2) 0.20360(16) 0.0287(11) Uani 1 1 d . . . . .
H47 H 0.4741 0.0322 0.2222 0.034 Uiso 1 1 calc R U . . .
C48 C 0.5706(7) 0.4949(2) 0.29749(18) 0.0395(12) Uani 1 1 d . . . . .
H48A H 0.5656 0.5178 0.3394 0.047 Uiso 1 1 calc R U . . .
H48B H 0.7260 0.4887 0.2886 0.047 Uiso 1 1 calc R U . . .
C49 C 0.5534(7) 0.5196(3) 0.20975(17) 0.0383(12) Uani 1 1 d . . . . .
H49A H 0.5069 0.4639 0.1935 0.046 Uiso 1 1 calc R U . . .
H49B H 0.7161 0.5302 0.2077 0.046 Uiso 1 1 calc R U . . .
C50 C 0.4404(7) 0.5593(2) 0.17375(18) 0.0358(12) Uani 1 1 d . . . . .
C51 C 0.2293(7) 0.5781(2) 0.18350(17) 0.0327(12) Uani 1 1 d . . . . .
H51 H 0.1544 0.5719 0.2155 0.039 Uiso 1 1 calc R U . . .
C52 C 0.1301(7) 0.6059(2) 0.14622(16) 0.0288(11) Uani 1 1 d . . . . .
H52 H -0.0158 0.6180 0.1512 0.035 Uiso 1 1 calc R U . . .
C53 C 0.2494(7) 0.6154(2) 0.10143(17) 0.0301(11) Uani 1 1 d . . . . .
H53 H 0.1859 0.6344 0.0748 0.036 Uiso 1 1 calc R U . . .
C54 C 0.4622(7) 0.5973(2) 0.09512(16) 0.0278(11) Uani 1 1 d . . . . .
C55 C 0.5919(7) 0.6053(2) 0.04803(17) 0.0291(11) Uani 1 1 d . . . . .
C56 C 0.6950(7) 0.6111(2) 0.00871(17) 0.0298(11) Uani 1 1 d . . . . .
C57 C 0.8189(7) 0.6162(2) -0.03913(16) 0.0276(11) Uani 1 1 d . . . . .
C58 C 1.0114(8) 0.5837(2) -0.05098(16) 0.0349(12) Uani 1 1 d . . . . .
H58 H 1.0620 0.5585 -0.0268 0.042 Uiso 1 1 calc R U . . .
C59 C 1.1299(7) 0.5878(2) -0.09751(17) 0.0344(12) Uani 1 1 d . . . . .
H59 H 1.2611 0.5654 -0.1054 0.041 Uiso 1 1 calc R U . . .
C60 C 1.0560(8) 0.6248(2) -0.13256(17) 0.0366(12) Uani 1 1 d . . . . .
H60 H 1.1366 0.6273 -0.1647 0.044 Uiso 1 1 calc R U . . .
C61 C 0.8676(8) 0.6580(3) -0.12133(18) 0.0389(13) Uani 1 1 d . . . . .
H61 H 0.8188 0.6833 -0.1457 0.047 Uiso 1 1 calc R U . . .
C62 C 0.7493(7) 0.6545(2) -0.07482(17) 0.0324(12) Uani 1 1 d . . . . .
H62 H 0.6203 0.6782 -0.0668 0.039 Uiso 1 1 calc R U . . .
C63 C 0.5993(7) 0.6241(3) 0.29837(19) 0.0450(13) Uani 1 1 d . . . . .
H63A H 0.5709 0.6561 0.2750 0.054 Uiso 1 1 calc R U . . .
H63B H 0.7616 0.6262 0.3026 0.054 Uiso 1 1 calc R U . . .
C64 C 0.5063(7) 0.6552(2) 0.35755(18) 0.0336(11) Uani 1 1 d . . . . .
C65 C 0.2925(7) 0.6687(2) 0.36202(18) 0.0373(12) Uani 1 1 d . . . . .
H65 H 0.1991 0.6574 0.3286 0.045 Uiso 1 1 calc R U . . .
C66 C 0.2124(7) 0.6989(2) 0.41523(18) 0.0340(12) Uani 1 1 d . . . . .
H66 H 0.0654 0.7102 0.4190 0.041 Uiso 1 1 calc R U . . .
C67 C 0.3492(8) 0.7122(2) 0.46241(19) 0.0384(12) Uani 1 1 d . . . . .
H67 H 0.2995 0.7331 0.4997 0.046 Uiso 1 1 calc R U . . .
C68 C 0.5591(9) 0.6947(3) 0.4548(2) 0.0473(14) Uani 1 1 d . . . . .
H68 H 0.6510 0.7025 0.4879 0.057 Uiso 1 1 calc R U . . .
N1 N 0.2446(5) -0.18347(17) 0.21883(14) 0.0259(9) Uani 1 1 d . . . . .
N2 N 0.2697(5) -0.07600(17) 0.35013(12) 0.0200(8) Uani 1 1 d . . . . .
N3 N 0.4705(5) 0.10935(18) 0.35121(12) 0.0204(8) Uani 1 1 d . . . . .
N4 N 0.2894(5) -0.09137(18) 0.49323(13) 0.0262(9) Uani 1 1 d . . . . .
N5 N 0.5281(5) 0.3562(2) 0.25823(14) 0.0320(9) Uani 1 1 d . . . . .
N6 N 0.4962(5) 0.54588(18) 0.26967(12) 0.0219(8) Uani 1 1 d . . . . .
N7 N 0.5595(5) 0.5697(2) 0.13131(14) 0.0366(10) Uani 1 1 d . . . . .
N8 N 0.6440(6) 0.6671(2) 0.40327(17) 0.0467(11) Uani 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 1.343(4) . ?
C1 C2 1.384(5) . ?
C1 C14 1.498(5) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.359(5) . ?
C5 C6 1.443(5) . ?
C6 C7A 1.201(14) . ?
C6 C7 1.225(6) . ?
C7 C8 1.432(6) . ?
C8 C9 1.378(6) . ?
C8 C13 1.391(7) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C7A C8A 1.433(9) . ?
C8A C9A 1.378(10) . ?
C8A C13A 1.392(10) . ?
C9A C10A 1.380(10) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.387(11) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.388(11) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.390(9) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14 N2 1.470(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N2 1.465(4) . ?
C15 C16 1.499(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.344(4) . ?
C16 C17 1.387(5) . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9500 . ?
C20 N3 1.359(5) . ?
C20 C21 1.447(5) . ?
C21 C22 1.202(5) . ?
C22 C23 1.435(5) . ?
C23 C24 1.388(5) . ?
C23 C28 1.391(5) . ?
C24 C25 1.381(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.379(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N2 1.470(4) . ?
C29 C30 1.508(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 N4 1.335(4) . ?
C30 C31 1.389(5) . ?
C31 C32 1.396(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.361(5) . ?
C33 H33 0.9500 . ?
C34 N4 1.341(4) . ?
C34 H34 0.9500 . ?
C35 N5 1.339(5) . ?
C35 C36 1.393(5) . ?
C35 C48 1.522(6) . ?
C36 C37 1.365(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.386(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.383(5) . ?
C38 H38 0.9500 . ?
C39 N5 1.358(5) . ?
C39 C40 1.433(6) . ?
C40 C41 1.187(6) . ?
C41 C42 1.454(6) . ?
C42 C47 1.390(5) . ?
C42 C43 1.397(5) . ?
C43 C44 1.370(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.392(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.393(6) . ?
C45 H45 0.9500 . ?
C46 C47 1.379(5) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 N6 1.465(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 N6 1.467(5) . ?
C49 C50 1.548(5) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 N7 1.332(5) . ?
C50 C51 1.387(5) . ?
C51 C52 1.374(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.377(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.388(5) . ?
C53 H53 0.9500 . ?
C54 N7 1.345(5) . ?
C54 C55 1.450(5) . ?
C55 C56 1.190(5) . ?
C56 C57 1.432(5) . ?
C57 C58 1.390(5) . ?
C57 C62 1.406(5) . ?
C58 C59 1.382(5) . ?
C58 H58 0.9500 . ?
C59 C60 1.385(5) . ?
C59 H59 0.9500 . ?
C60 C61 1.373(6) . ?
C60 H60 0.9500 . ?
C61 C62 1.378(5) . ?
C61 H61 0.9500 . ?
C62 H62 0.9500 . ?
C63 N6 1.453(5) . ?
C63 C64 1.539(6) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 N8 1.348(5) . ?
C64 C65 1.364(5) . ?
C65 C66 1.380(5) . ?
C65 H65 0.9500 . ?
C66 C67 1.367(6) . ?
C66 H66 0.9500 . ?
C67 C68 1.367(6) . ?
C67 H67 0.9500 . ?
C68 N8 1.352(5) . ?
C68 H68 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.4(4) . . ?
N1 C1 C14 116.5(4) . . ?
C2 C1 C14 121.0(3) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 C6 116.7(4) . . ?
C4 C5 C6 120.5(4) . . ?
C7A C6 C5 155.5(10) . . ?
C7 C6 C5 178.9(5) . . ?
C6 C7 C8 173.1(5) . . ?
C9 C8 C13 119.3(5) . . ?
C9 C8 C7 121.4(5) . . ?
C13 C8 C7 119.2(5) . . ?
C8 C9 C10 121.2(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 119.7(6) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.7(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C6 C7A C8A 169.7(14) . . ?
C9A C8A C13A 119.5(10) . . ?
C9A C8A C7A 121.3(11) . . ?
C13A C8A C7A 119.1(11) . . ?
C8A C9A C10A 121.9(11) . . ?
C8A C9A H9A 119.1 . . ?
C10A C9A H9A 119.1 . . ?
C11A C10A C9A 118.6(11) . . ?
C11A C10A H10A 120.7 . . ?
C9A C10A H10A 120.7 . . ?
C10A C11A C12A 120.4(11) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A H11A 119.8 . . ?
C13A C12A C11A 120.4(11) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C8A 119.2(11) . . ?
C12A C13A H13A 120.4 . . ?
C8A C13A H13A 120.4 . . ?
N2 C14 C1 110.9(3) . . ?
N2 C14 H14A 109.5 . . ?
C1 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 C16 111.5(3) . . ?
N2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N3 C16 C17 123.0(4) . . ?
N3 C16 C15 116.8(4) . . ?
C17 C16 C15 120.2(4) . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 118.2(4) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 119.3(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N3 C20 C19 123.3(3) . . ?
N3 C20 C21 116.2(4) . . ?
C19 C20 C21 120.5(4) . . ?
C22 C21 C20 178.1(4) . . ?
C21 C22 C23 179.3(5) . . ?
C24 C23 C28 118.5(3) . . ?
C24 C23 C22 121.7(4) . . ?
C28 C23 C22 119.8(4) . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 119.9(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 119.9(4) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C23 120.9(4) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
N2 C29 C30 114.6(3) . . ?
N2 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
N2 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
N4 C30 C31 123.0(3) . . ?
N4 C30 C29 115.8(3) . . ?
C31 C30 C29 121.1(3) . . ?
C30 C31 C32 118.3(4) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
C33 C32 C31 118.4(4) . . ?
C33 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C34 C33 C32 119.0(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
N4 C34 C33 123.9(4) . . ?
N4 C34 H34 118.1 . . ?
C33 C34 H34 118.1 . . ?
N5 C35 C36 123.7(4) . . ?
N5 C35 C48 117.0(4) . . ?
C36 C35 C48 119.3(4) . . ?
C37 C36 C35 118.9(4) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C36 C37 C38 118.6(4) . . ?
C36 C37 H37 120.7 . . ?
C38 C37 H37 120.7 . . ?
C39 C38 C37 119.5(4) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
N5 C39 C38 122.5(4) . . ?
N5 C39 C40 116.6(4) . . ?
C38 C39 C40 120.9(4) . . ?
C41 C40 C39 176.9(4) . . ?
C40 C41 C42 177.5(4) . . ?
C47 C42 C43 118.9(4) . . ?
C47 C42 C41 120.1(4) . . ?
C43 C42 C41 120.9(4) . . ?
C44 C43 C42 120.9(4) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 120.1(4) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 119.4(4) . . ?
C46 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
C47 C46 C45 120.3(4) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C42 120.4(4) . . ?
C46 C47 H47 119.8 . . ?
C42 C47 H47 119.8 . . ?
N6 C48 C35 111.0(3) . . ?
N6 C48 H48A 109.4 . . ?
C35 C48 H48A 109.4 . . ?
N6 C48 H48B 109.4 . . ?
C35 C48 H48B 109.4 . . ?
H48A C48 H48B 108.0 . . ?
N6 C49 C50 111.8(4) . . ?
N6 C49 H49A 109.3 . . ?
C50 C49 H49A 109.3 . . ?
N6 C49 H49B 109.3 . . ?
C50 C49 H49B 109.3 . . ?
H49A C49 H49B 107.9 . . ?
N7 C50 C51 123.8(4) . . ?
N7 C50 C49 113.8(4) . . ?
C51 C50 C49 122.3(3) . . ?
C52 C51 C50 119.2(4) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C53 C52 C51 117.7(4) . . ?
C53 C52 H52 121.2 . . ?
C51 C52 H52 121.2 . . ?
C52 C53 C54 120.1(4) . . ?
C52 C53 H53 120.0 . . ?
C54 C53 H53 120.0 . . ?
N7 C54 C53 122.4(3) . . ?
N7 C54 C55 115.8(4) . . ?
C53 C54 C55 121.7(4) . . ?
C56 C55 C54 178.8(5) . . ?
C55 C56 C57 178.6(4) . . ?
C58 C57 C62 118.7(4) . . ?
C58 C57 C56 120.7(4) . . ?
C62 C57 C56 120.7(4) . . ?
C59 C58 C57 120.8(4) . . ?
C59 C58 H58 119.6 . . ?
C57 C58 H58 119.6 . . ?
C58 C59 C60 119.5(4) . . ?
C58 C59 H59 120.3 . . ?
C60 C59 H59 120.3 . . ?
C61 C60 C59 120.8(4) . . ?
C61 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C60 C61 C62 120.1(4) . . ?
C60 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C61 C62 C57 120.3(4) . . ?
C61 C62 H62 119.9 . . ?
C57 C62 H62 119.9 . . ?
N6 C63 C64 110.4(3) . . ?
N6 C63 H63A 109.6 . . ?
C64 C63 H63A 109.6 . . ?
N6 C63 H63B 109.6 . . ?
C64 C63 H63B 109.6 . . ?
H63A C63 H63B 108.1 . . ?
N8 C64 C65 122.9(4) . . ?
N8 C64 C63 117.0(4) . . ?
C65 C64 C63 120.1(4) . . ?
C64 C65 C66 119.7(4) . . ?
C64 C65 H65 120.1 . . ?
C66 C65 H65 120.1 . . ?
C67 C66 C65 118.6(4) . . ?
C67 C66 H66 120.7 . . ?
C65 C66 H66 120.7 . . ?
C66 C67 C68 118.6(4) . . ?
C66 C67 H67 120.7 . . ?
C68 C67 H67 120.7 . . ?
N8 C68 C67 124.1(4) . . ?
N8 C68 H68 117.9 . . ?
C67 C68 H68 117.9 . . ?
C1 N1 C5 117.4(4) . . ?
C15 N2 C14 111.3(3) . . ?
C15 N2 C29 109.6(3) . . ?
C14 N2 C29 111.6(3) . . ?
C16 N3 C20 116.7(3) . . ?
C30 N4 C34 117.4(3) . . ?
C35 N5 C39 116.7(4) . . ?
C63 N6 C48 110.6(3) . . ?
C63 N6 C49 111.1(3) . . ?
C48 N6 C49 107.9(3) . . ?
C50 N7 C54 116.8(4) . . ?
C64 N8 C68 116.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.6(6) . . . . ?
C14 C1 C2 C3 176.1(4) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 N1 1.1(6) . . . . ?
C3 C4 C5 C6 -177.6(4) . . . . ?
N1 C5 C6 C7A -115(3) . . . . ?
C4 C5 C6 C7A 64(3) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 0.8(7) . . . . ?
C11 C12 C13 C8 -0.3(7) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C7 C8 C13 C12 179.2(4) . . . . ?
C7 C6 C7A C8A -6(8) . . . . ?
C5 C6 C7A C8A 175(8) . . . . ?
C6 C7A C8A C9A -112(10) . . . . ?
C6 C7A C8A C13A 68(10) . . . . ?
C13A C8A C9A C10A 0.0(3) . . . . ?
C7A C8A C9A C10A -180.0(3) . . . . ?
C8A C9A C10A C11A 0.0(3) . . . . ?
C9A C10A C11A C12A 0.0(7) . . . . ?
C10A C11A C12A C13A 0.0(9) . . . . ?
C11A C12A C13A C8A 0.1(9) . . . . ?
C9A C8A C13A C12A -0.1(7) . . . . ?
C7A C8A C13A C12A 179.9(5) . . . . ?
N1 C1 C14 N2 92.6(4) . . . . ?
C2 C1 C14 N2 -83.1(4) . . . . ?
N2 C15 C16 N3 128.6(3) . . . . ?
N2 C15 C16 C17 -54.0(4) . . . . ?
N3 C16 C17 C18 1.3(5) . . . . ?
C15 C16 C17 C18 -175.9(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 N3 -0.6(5) . . . . ?
C18 C19 C20 C21 -179.5(3) . . . . ?
C28 C23 C24 C25 -1.9(5) . . . . ?
C22 C23 C24 C25 176.2(4) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C24 C25 C26 C27 0.5(6) . . . . ?
C25 C26 C27 C28 -1.9(6) . . . . ?
C26 C27 C28 C23 1.4(6) . . . . ?
C24 C23 C28 C27 0.5(5) . . . . ?
C22 C23 C28 C27 -177.7(3) . . . . ?
N2 C29 C30 N4 151.6(3) . . . . ?
N2 C29 C30 C31 -31.1(5) . . . . ?
N4 C30 C31 C32 0.7(6) . . . . ?
C29 C30 C31 C32 -176.3(4) . . . . ?
C30 C31 C32 C33 -0.1(6) . . . . ?
C31 C32 C33 C34 0.6(6) . . . . ?
C32 C33 C34 N4 -1.6(6) . . . . ?
N5 C35 C36 C37 3.3(6) . . . . ?
C48 C35 C36 C37 -172.8(4) . . . . ?
C35 C36 C37 C38 -1.2(6) . . . . ?
C36 C37 C38 C39 -1.7(5) . . . . ?
C37 C38 C39 N5 2.7(5) . . . . ?
C37 C38 C39 C40 -179.0(3) . . . . ?
C47 C42 C43 C44 -2.3(6) . . . . ?
C41 C42 C43 C44 176.0(4) . . . . ?
C42 C43 C44 C45 0.1(7) . . . . ?
C43 C44 C45 C46 2.4(7) . . . . ?
C44 C45 C46 C47 -2.7(7) . . . . ?
C45 C46 C47 C42 0.5(6) . . . . ?
C43 C42 C47 C46 2.0(6) . . . . ?
C41 C42 C47 C46 -176.3(4) . . . . ?
N5 C35 C48 N6 127.8(4) . . . . ?
C36 C35 C48 N6 -55.8(5) . . . . ?
N6 C49 C50 N7 147.7(4) . . . . ?
N6 C49 C50 C51 -35.6(6) . . . . ?
N7 C50 C51 C52 3.2(7) . . . . ?
C49 C50 C51 C52 -173.2(4) . . . . ?
C50 C51 C52 C53 -1.6(6) . . . . ?
C51 C52 C53 C54 -0.1(6) . . . . ?
C52 C53 C54 N7 0.5(6) . . . . ?
C52 C53 C54 C55 179.0(4) . . . . ?
C62 C57 C58 C59 -1.2(6) . . . . ?
C56 C57 C58 C59 179.3(4) . . . . ?
C57 C58 C59 C60 0.2(6) . . . . ?
C58 C59 C60 C61 0.5(6) . . . . ?
C59 C60 C61 C62 -0.1(7) . . . . ?
C60 C61 C62 C57 -0.9(6) . . . . ?
C58 C57 C62 C61 1.6(6) . . . . ?
C56 C57 C62 C61 -178.9(4) . . . . ?
N6 C63 C64 N8 110.0(4) . . . . ?
N6 C63 C64 C65 -69.1(5) . . . . ?
N8 C64 C65 C66 2.9(7) . . . . ?
C63 C64 C65 C66 -178.0(4) . . . . ?
C64 C65 C66 C67 -2.1(6) . . . . ?
C65 C66 C67 C68 -0.3(6) . . . . ?
C66 C67 C68 N8 2.2(7) . . . . ?
C2 C1 N1 C5 0.8(6) . . . . ?
C14 C1 N1 C5 -174.9(3) . . . . ?
C4 C5 N1 C1 -1.7(6) . . . . ?
C6 C5 N1 C1 177.1(3) . . . . ?
C16 C15 N2 C14 154.4(3) . . . . ?
C16 C15 N2 C29 -81.7(4) . . . . ?
C1 C14 N2 C15 -73.1(4) . . . . ?
C1 C14 N2 C29 164.2(3) . . . . ?
C30 C29 N2 C15 164.7(3) . . . . ?
C30 C29 N2 C14 -71.6(4) . . . . ?
C17 C16 N3 C20 -1.9(5) . . . . ?
C15 C16 N3 C20 175.4(3) . . . . ?
C19 C20 N3 C16 1.5(5) . . . . ?
C21 C20 N3 C16 -179.6(3) . . . . ?
C31 C30 N4 C34 -1.7(6) . . . . ?
C29 C30 N4 C34 175.5(3) . . . . ?
C33 C34 N4 C30 2.2(6) . . . . ?
C36 C35 N5 C39 -2.3(6) . . . . ?
C48 C35 N5 C39 173.9(3) . . . . ?
C38 C39 N5 C35 -0.7(5) . . . . ?
C40 C39 N5 C35 -179.1(3) . . . . ?
C64 C63 N6 C48 -70.0(5) . . . . ?
C64 C63 N6 C49 170.1(3) . . . . ?
C35 C48 N6 C63 166.3(3) . . . . ?
C35 C48 N6 C49 -71.9(4) . . . . ?
C50 C49 N6 C63 -70.2(4) . . . . ?
C50 C49 N6 C48 168.4(3) . . . . ?
C51 C50 N7 C54 -2.7(6) . . . . ?
C49 C50 N7 C54 173.9(4) . . . . ?
C53 C54 N7 C50 0.9(6) . . . . ?
C55 C54 N7 C50 -177.7(4) . . . . ?
C65 C64 N8 C68 -1.1(6) . . . . ?
C63 C64 N8 C68 179.8(4) . . . . ?
C67 C68 N8 C64 -1.5(7) . . . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1028488'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 N4, Cu 2+, C2 H3 N, 2 Cl O4 1-'
_chemical_formula_sum            'C36 H29 Cl2 Cu N5 O8'
_chemical_formula_weight         794.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6528(11)
_cell_length_b                   12.4257(13)
_cell_length_c                   13.8814(15)
_cell_angle_alpha                99.698(3)
_cell_angle_beta                 111.246(3)
_cell_angle_gamma                100.405(2)
_cell_volume                     1781.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8127
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prisms
_exptl_crystal_colour            blue-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             814
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.822
_shelx_estimated_absorpt_T_min   0.740
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37865
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.999
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8127
_reflns_number_gt                7524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;




_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
 One of the perchlorate anions was disordered.  The disorder was modeled 
by assigning the variable x to the site occupancy for one component of the 
disordered anion and (1-x) to the site occupancy for the alternate component.  
The displacement parameters for the oxygen atoms of both components were 
constrained to be equal while refining x.  A separate constraint was applied 
to the displacement parameters for the Cl atoms.  The geometry of the two 
anions were restrained to be equivalent throughout the refinement process.  
In this way, the major component of the disorder consisting of atoms, O1, O2, 
O3, O4 and Cl1 had a site occupancy of 73(2)%.   
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+1.4027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8127
_refine_ls_number_parameters     493
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.055
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55010(17) 0.73287(14) 0.36346(14) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.45027(19) 0.78188(15) 0.35841(15) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.4648 0.8512 0.4076 0.029 Uiso 1 1 calc R U . . .
C3 C 0.32958(19) 0.72760(17) 0.28029(16) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.2597 0.7587 0.2758 0.034 Uiso 1 1 calc R U . . .
C4 C 0.31148(18) 0.62718(16) 0.20845(16) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.2294 0.5891 0.1540 0.032 Uiso 1 1 calc R U . . .
C5 C 0.41555(17) 0.58315(15) 0.21743(14) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.40239(17) 0.48026(15) 0.14416(14) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.39290(17) 0.39399(15) 0.08496(15) 0.0232(4) Uani 1 1 d . . . . .
C8 C 0.39216(18) 0.29053(15) 0.02006(14) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.4742(2) 0.29272(16) -0.03299(15) 0.0268(4) Uani 1 1 d . . . . .
H9 H 0.5258 0.3629 -0.0298 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4801(2) 0.19239(18) -0.09021(16) 0.0332(4) Uani 1 1 d . . . . .
H10 H 0.5364 0.1938 -0.1255 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4037(2) 0.09006(18) -0.09588(18) 0.0401(5) Uani 1 1 d . . . . .
H11 H 0.4071 0.0216 -0.1359 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3225(2) 0.08693(18) -0.04354(19) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.2711 0.0164 -0.0473 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3159(2) 0.18683(17) 0.01460(17) 0.0332(4) Uani 1 1 d . . . . .
H13 H 0.2601 0.1846 0.0503 0.040 Uiso 1 1 calc R U . . .
C14 C 0.68265(17) 0.78450(14) 0.44950(14) 0.0212(3) Uani 1 1 d . . . . .
H14A H 0.6976 0.8676 0.4715 0.025 Uiso 1 1 calc R U . . .
H14B H 0.6911 0.7546 0.5128 0.025 Uiso 1 1 calc R U . . .
C15 C 0.90173(18) 0.76432(15) 0.49770(15) 0.0244(4) Uani 1 1 d . . . . .
H15A H 0.9268 0.8349 0.5542 0.029 Uiso 1 1 calc R U . . .
H15B H 0.9696 0.7658 0.4706 0.029 Uiso 1 1 calc R U . . .
C16 C 0.88742(17) 0.66380(15) 0.54356(14) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.9735(2) 0.66255(17) 0.64325(16) 0.0299(4) Uani 1 1 d . . . . .
H17 H 1.0434 0.7264 0.6857 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9553(2) 0.56675(18) 0.67924(16) 0.0341(5) Uani 1 1 d . . . . .
H18 H 1.0150 0.5625 0.7457 0.041 Uiso 1 1 calc R U . . .
C19 C 0.8493(2) 0.47650(17) 0.61784(16) 0.0306(4) Uani 1 1 d . . . . .
H19 H 0.8351 0.4105 0.6424 0.037 Uiso 1 1 calc R U . . .
C20 C 0.76402(18) 0.48370(15) 0.51982(15) 0.0235(4) Uani 1 1 d . . . . .
C21 C 0.64622(19) 0.39835(16) 0.45805(15) 0.0249(4) Uani 1 1 d . . . . .
C22 C 0.54479(19) 0.32997(16) 0.40861(15) 0.0257(4) Uani 1 1 d . . . . .
C23 C 0.42377(18) 0.24987(16) 0.34489(15) 0.0246(4) Uani 1 1 d . . . . .
C24 C 0.3165(2) 0.28832(19) 0.29563(17) 0.0314(4) Uani 1 1 d . . . . .
H24 H 0.3242 0.3672 0.3046 0.038 Uiso 1 1 calc R U . . .
C25 C 0.1990(2) 0.2112(2) 0.23372(18) 0.0397(5) Uani 1 1 d . . . . .
H25 H 0.1262 0.2373 0.2007 0.048 Uiso 1 1 calc R U . . .
C26 C 0.1880(2) 0.0964(2) 0.22008(19) 0.0447(6) Uani 1 1 d . . . . .
H26 H 0.1075 0.0439 0.1774 0.054 Uiso 1 1 calc R U . . .
C27 C 0.2934(2) 0.0574(2) 0.26817(19) 0.0421(5) Uani 1 1 d . . . . .
H27 H 0.2849 -0.0217 0.2580 0.050 Uiso 1 1 calc R U . . .
C28 C 0.4113(2) 0.13325(17) 0.33112(17) 0.0310(4) Uani 1 1 d . . . . .
H28 H 0.4833 0.1064 0.3647 0.037 Uiso 1 1 calc R U . . .
C29 C 0.80028(18) 0.82950(14) 0.33879(14) 0.0221(4) Uani 1 1 d . . . . .
H29A H 0.8644 0.9019 0.3825 0.026 Uiso 1 1 calc R U . . .
H29B H 0.7196 0.8466 0.2976 0.026 Uiso 1 1 calc R U . . .
C30 C 0.84648(17) 0.76721(15) 0.26378(14) 0.0217(3) Uani 1 1 d . . . . .
C31 C 0.92575(19) 0.82193(17) 0.22266(16) 0.0282(4) Uani 1 1 d . . . . .
H31 H 0.9562 0.9021 0.2435 0.034 Uiso 1 1 calc R U . . .
C32 C 0.9599(2) 0.75777(18) 0.15050(17) 0.0314(4) Uani 1 1 d . . . . .
H32 H 1.0148 0.7933 0.1219 0.038 Uiso 1 1 calc R U . . .
C33 C 0.91255(19) 0.64100(18) 0.12097(16) 0.0281(4) Uani 1 1 d . . . . .
H33 H 0.9332 0.5955 0.0707 0.034 Uiso 1 1 calc R U . . .
C34 C 0.83502(17) 0.59163(16) 0.16550(14) 0.0232(4) Uani 1 1 d . . . . .
H34 H 0.8032 0.5116 0.1454 0.028 Uiso 1 1 calc R U . . .
C35 C 0.66746(17) 0.33984(15) 0.23216(14) 0.0203(3) Uani 1 1 d . . . . .
C36 C 0.64738(19) 0.21795(15) 0.20288(15) 0.0248(4) Uani 1 1 d . . . . .
H36A H 0.6756 0.1908 0.2678 0.037 Uiso 1 1 calc R U . . .
H36B H 0.6966 0.1991 0.1612 0.037 Uiso 1 1 calc R U . . .
H36C H 0.5565 0.1817 0.1599 0.037 Uiso 1 1 calc R U . . .
N1 N 0.53417(14) 0.63507(12) 0.29490(11) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.77931(14) 0.75749(12) 0.40934(12) 0.0195(3) Uani 1 1 d . . . . .
N3 N 0.78631(14) 0.57534(12) 0.48133(12) 0.0209(3) Uani 1 1 d . . . . .
N4 N 0.80320(14) 0.65367(12) 0.23663(12) 0.0201(3) Uani 1 1 d . . . . .
N5 N 0.68157(15) 0.43498(13) 0.25743(12) 0.0220(3) Uani 1 1 d . . . . .
Cl1 Cl 0.78791(10) 0.10604(8) 0.50539(10) 0.0178(2) Uani 0.729 1 d D U P A 1
O1 O 0.83836(19) 0.22110(14) 0.5672(2) 0.0372(5) Uani 0.729 1 d D U P A 1
O2 O 0.7709(3) 0.1045(2) 0.39653(17) 0.0436(6) Uani 0.729 1 d D U P A 1
O3 O 0.66818(19) 0.05749(18) 0.5079(2) 0.0334(5) Uani 0.729 1 d D U P A 1
O4 O 0.87683(19) 0.04075(18) 0.54556(19) 0.0206(4) Uani 0.729 1 d D U P A 1
Cl1A Cl 0.7770(4) 0.1089(3) 0.4809(3) 0.0260(9) Uiso 0.271 1 d D U P B 2
O1A O 0.8202(9) 0.2224(6) 0.4811(8) 0.081(2) Uiso 0.271 1 d D U P B 2
O2A O 0.6903(7) 0.0483(6) 0.3758(5) 0.0544(17) Uiso 0.271 1 d D U P B 2
O3A O 0.7037(10) 0.0987(9) 0.5452(8) 0.082(3) Uiso 0.271 1 d D U P B 2
O4A O 0.8800(6) 0.0560(6) 0.5189(6) 0.0237(18) Uiso 0.271 1 d D U P B 2
Cl2 Cl 0.85966(4) 0.25793(4) 0.03775(3) 0.02471(10) Uani 1 1 d . . . . .
O5 O 0.80174(15) 0.18938(13) -0.07026(11) 0.0348(3) Uani 1 1 d . . . . .
O6 O 0.87504(15) 0.18645(13) 0.11064(12) 0.0342(3) Uani 1 1 d . . . . .
O7 O 0.98252(16) 0.32870(15) 0.05875(13) 0.0433(4) Uani 1 1 d . . . . .
O8 O 0.77883(17) 0.32782(14) 0.05431(14) 0.0420(4) Uani 1 1 d . . . . .
Cu1 Cu 0.71324(2) 0.59504(2) 0.32536(2) 0.01759(7) Uani 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 1.348(2) . ?
C1 C2 1.393(2) . ?
C1 C14 1.507(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.360(2) . ?
C5 C6 1.439(2) . ?
C6 C7 1.196(3) . ?
C7 C8 1.437(3) . ?
C8 C13 1.400(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.490(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N2 1.483(2) . ?
C15 C16 1.504(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.348(2) . ?
C16 C17 1.389(3) . ?
C17 C18 1.377(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(3) . ?
C19 H19 0.9500 . ?
C20 N3 1.359(2) . ?
C20 C21 1.435(3) . ?
C21 C22 1.201(3) . ?
C22 C23 1.433(3) . ?
C23 C24 1.401(3) . ?
C23 C28 1.403(3) . ?
C24 C25 1.388(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N2 1.486(2) . ?
C29 C30 1.503(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 N4 1.346(2) . ?
C30 C31 1.388(3) . ?
C31 C32 1.390(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.381(3) . ?
C33 H33 0.9500 . ?
C34 N4 1.349(2) . ?
C34 H34 0.9500 . ?
C35 N5 1.138(2) . ?
C35 C36 1.452(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N1 Cu1 2.1418(15) . ?
N2 Cu1 2.0055(14) . ?
N3 Cu1 2.0953(15) . ?
N4 Cu1 2.0270(15) . ?
N5 Cu1 1.9574(15) . ?
Cl1 O1 1.4293(19) . ?
Cl1 O3 1.432(2) . ?
Cl1 O4 1.442(2) . ?
Cl1 O2 1.447(2) . ?
Cl1A O1A 1.409(7) . ?
Cl1A O2A 1.415(6) . ?
Cl1A O4A 1.447(6) . ?
Cl1A O3A 1.447(7) . ?
Cl2 O5 1.4344(14) . ?
Cl2 O7 1.4368(16) . ?
Cl2 O6 1.4399(15) . ?
Cl2 O8 1.4420(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 122.71(17) . . ?
N1 C1 C14 115.73(15) . . ?
C2 C1 C14 121.52(16) . . ?
C3 C2 C1 118.67(17) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.44(17) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.99(17) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.98(16) . . ?
N1 C5 C6 116.79(15) . . ?
C4 C5 C6 121.23(16) . . ?
C7 C6 C5 178.7(2) . . ?
C6 C7 C8 175.1(2) . . ?
C13 C8 C9 119.68(18) . . ?
C13 C8 C7 120.54(18) . . ?
C9 C8 C7 119.66(17) . . ?
C10 C9 C8 120.04(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
N2 C14 C1 110.16(14) . . ?
N2 C14 H14A 109.6 . . ?
C1 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
C1 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 C16 109.79(14) . . ?
N2 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C17 122.49(18) . . ?
N3 C16 C15 115.60(16) . . ?
C17 C16 C15 121.91(17) . . ?
C18 C17 C16 118.61(19) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.61(19) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 119.30(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N3 C20 C19 121.01(18) . . ?
N3 C20 C21 117.15(16) . . ?
C19 C20 C21 121.77(18) . . ?
C22 C21 C20 176.9(2) . . ?
C21 C22 C23 177.2(2) . . ?
C24 C23 C28 119.53(19) . . ?
C24 C23 C22 119.70(18) . . ?
C28 C23 C22 120.76(18) . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 119.7(2) . . ?
C27 C28 H28 120.2 . . ?
C23 C28 H28 120.2 . . ?
N2 C29 C30 108.76(14) . . ?
N2 C29 H29A 109.9 . . ?
C30 C29 H29A 109.9 . . ?
N2 C29 H29B 109.9 . . ?
C30 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N4 C30 C31 121.74(17) . . ?
N4 C30 C29 115.34(15) . . ?
C31 C30 C29 122.90(16) . . ?
C30 C31 C32 119.06(18) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C33 C32 C31 118.89(18) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C34 C33 C32 119.23(18) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
N4 C34 C33 121.94(17) . . ?
N4 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
N5 C35 C36 177.81(19) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C1 N1 C5 118.20(15) . . ?
C1 N1 Cu1 110.49(11) . . ?
C5 N1 Cu1 131.18(12) . . ?
C15 N2 C29 110.84(14) . . ?
C15 N2 C14 112.02(14) . . ?
C29 N2 C14 112.05(14) . . ?
C15 N2 Cu1 105.38(11) . . ?
C29 N2 Cu1 108.92(10) . . ?
C14 N2 Cu1 107.31(10) . . ?
C16 N3 C20 118.78(16) . . ?
C16 N3 Cu1 109.25(12) . . ?
C20 N3 Cu1 130.61(12) . . ?
C30 N4 C34 119.11(16) . . ?
C30 N4 Cu1 113.48(12) . . ?
C34 N4 Cu1 126.92(13) . . ?
C35 N5 Cu1 170.28(15) . . ?
O1 Cl1 O3 110.69(14) . . ?
O1 Cl1 O4 110.20(14) . . ?
O3 Cl1 O4 109.75(15) . . ?
O1 Cl1 O2 107.91(16) . . ?
O3 Cl1 O2 109.95(18) . . ?
O4 Cl1 O2 108.29(14) . . ?
O1A Cl1A O2A 108.6(5) . . ?
O1A Cl1A O4A 112.8(5) . . ?
O2A Cl1A O4A 110.3(5) . . ?
O1A Cl1A O3A 111.6(6) . . ?
O2A Cl1A O3A 104.9(6) . . ?
O4A Cl1A O3A 108.4(5) . . ?
O5 Cl2 O7 110.20(9) . . ?
O5 Cl2 O6 109.71(9) . . ?
O7 Cl2 O6 109.14(10) . . ?
O5 Cl2 O8 109.51(10) . . ?
O7 Cl2 O8 109.43(11) . . ?
O6 Cl2 O8 108.82(10) . . ?
N5 Cu1 N2 169.26(6) . . ?
N5 Cu1 N4 95.10(6) . . ?
N2 Cu1 N4 82.44(6) . . ?
N5 Cu1 N3 94.37(6) . . ?
N2 Cu1 N3 79.62(6) . . ?
N4 Cu1 N3 130.83(6) . . ?
N5 Cu1 N1 109.06(6) . . ?
N2 Cu1 N1 81.40(6) . . ?
N4 Cu1 N1 113.62(6) . . ?
N3 Cu1 N1 108.36(6) . . ?

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 0.5(3) . . . . ?
C14 C1 C2 C3 -177.17(17) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 N1 0.5(3) . . . . ?
C3 C4 C5 C6 -179.12(17) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 175.83(18) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C7 C8 C13 C12 -176.10(19) . . . . ?
N1 C1 C14 N2 31.5(2) . . . . ?
C2 C1 C14 N2 -150.74(16) . . . . ?
N2 C15 C16 N3 17.8(2) . . . . ?
N2 C15 C16 C17 -162.53(17) . . . . ?
N3 C16 C17 C18 0.6(3) . . . . ?
C15 C16 C17 C18 -178.97(18) . . . . ?
C16 C17 C18 C19 -2.8(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 N3 3.2(3) . . . . ?
C18 C19 C20 C21 -173.43(19) . . . . ?
C28 C23 C24 C25 0.0(3) . . . . ?
C22 C23 C24 C25 179.95(19) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C26 C27 C28 C23 -0.7(3) . . . . ?
C24 C23 C28 C27 0.6(3) . . . . ?
C22 C23 C28 C27 -179.4(2) . . . . ?
N2 C29 C30 N4 30.9(2) . . . . ?
N2 C29 C30 C31 -150.65(18) . . . . ?
N4 C30 C31 C32 0.8(3) . . . . ?
C29 C30 C31 C32 -177.53(18) . . . . ?
C30 C31 C32 C33 0.7(3) . . . . ?
C31 C32 C33 C34 -1.3(3) . . . . ?
C32 C33 C34 N4 0.4(3) . . . . ?
C2 C1 N1 C5 0.5(3) . . . . ?
C14 C1 N1 C5 178.21(15) . . . . ?
C2 C1 N1 Cu1 176.84(14) . . . . ?
C14 C1 N1 Cu1 -5.41(18) . . . . ?
C4 C5 N1 C1 -0.9(3) . . . . ?
C6 C5 N1 C1 178.68(15) . . . . ?
C4 C5 N1 Cu1 -176.43(13) . . . . ?
C6 C5 N1 Cu1 3.2(2) . . . . ?
C16 C15 N2 C29 -160.04(14) . . . . ?
C16 C15 N2 C14 73.99(18) . . . . ?
C16 C15 N2 Cu1 -42.37(16) . . . . ?
C30 C29 N2 C15 79.92(17) . . . . ?
C30 C29 N2 C14 -154.14(14) . . . . ?
C30 C29 N2 Cu1 -35.58(16) . . . . ?
C1 C14 N2 C15 -157.08(14) . . . . ?
C1 C14 N2 C29 77.62(17) . . . . ?
C1 C14 N2 Cu1 -41.89(16) . . . . ?
C17 C16 N3 C20 3.4(3) . . . . ?
C15 C16 N3 C20 -176.92(16) . . . . ?
C17 C16 N3 Cu1 -164.65(15) . . . . ?
C15 C16 N3 Cu1 14.99(19) . . . . ?
C19 C20 N3 C16 -5.3(3) . . . . ?
C21 C20 N3 C16 171.42(16) . . . . ?
C19 C20 N3 Cu1 159.79(14) . . . . ?
C21 C20 N3 Cu1 -23.5(2) . . . . ?
C31 C30 N4 C34 -1.7(3) . . . . ?
C29 C30 N4 C34 176.75(16) . . . . ?
C31 C30 N4 Cu1 170.80(15) . . . . ?
C29 C30 N4 Cu1 -10.71(19) . . . . ?
C33 C34 N4 C30 1.1(3) . . . . ?
C33 C34 N4 Cu1 -170.31(14) . . . . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1028489'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30 N4, Cu 2+, 2 Cl O4 1-, C2 H3 N'
_chemical_formula_sum            'C44 H33 Cl2 Cu N5 O8'
_chemical_formula_weight         894.19

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7070(14)
_cell_length_b                   13.1550(15)
_cell_length_c                   14.596(2)
_cell_angle_alpha                116.759(3)
_cell_angle_beta                 107.160(3)
_cell_angle_gamma                90.037(4)
_cell_volume                     2056.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    6722
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prisms
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             918
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.722
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23144
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.656
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             5877
_reflns_number_gt                4085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'






_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5877
_refine_ls_number_parameters     543
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2074
_refine_ls_wR_factor_gt          0.1916
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_restrained_S_all      1.291
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6998(7) 0.3410(6) 0.8479(7) 0.049(2) Uani 1 1 d . U . . .
C2 C 0.7526(8) 0.4166(7) 0.8230(8) 0.057(3) Uani 1 1 d . U . . .
H2 H 0.8201 0.4661 0.8744 0.069 Uiso 1 1 calc R U . . .
C3 C 0.7116(8) 0.4193(9) 0.7345(9) 0.060(3) Uani 1 1 d . U . . .
H3 H 0.7496 0.4715 0.7219 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6131(8) 0.3494(7) 0.6538(9) 0.073(3) Uani 1 1 d . U . . .
H4 H 0.5823 0.3518 0.5873 0.088 Uiso 1 1 calc R U . . .
C5 C 0.5632(7) 0.2743(7) 0.6804(7) 0.048(2) Uani 1 1 d . U . . .
C6 C 0.4671(7) 0.1952(8) 0.6041(7) 0.051(2) Uani 1 1 d . U . . .
C7 C 0.3871(7) 0.1240(7) 0.5395(7) 0.0437(19) Uani 1 1 d . U . . .
C8 C 0.2868(9) 0.0366(8) 0.4656(8) 0.042(2) Uani 1 1 d . U . . .
C9 C 0.2930(8) -0.0666(8) 0.4693(8) 0.044(2) Uani 1 1 d . U . . .
H9 H 0.3558 -0.0799 0.5149 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1981(9) -0.1493(9) 0.3995(9) 0.053(3) Uani 1 1 d . U . . .
H10 H 0.2015 -0.2233 0.3953 0.064 Uiso 1 1 calc R U . . .
C11 C 0.0993(8) -0.1364(9) 0.3353(8) 0.056(3) Uani 1 1 d . U . . .
H11 H 0.0327 -0.1910 0.2969 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1139(10) -0.0273(10) 0.3364(11) 0.068(3) Uani 1 1 d . U . . .
H12 H 0.0581 -0.0180 0.2820 0.082 Uiso 1 1 calc R U . . .
C13 C 0.1954(9) 0.0629(9) 0.4035(9) 0.050(3) Uani 1 1 d . U . . .
H13 H 0.1914 0.1372 0.4084 0.060 Uiso 1 1 calc R U . . .
C14 C 0.7492(6) 0.3403(6) 0.9521(6) 0.0466(19) Uani 1 1 d D U . . .
H14A H 0.7271 0.4033 1.0094 0.056 Uiso 1 1 calc R U . . .
H14B H 0.8316 0.3527 0.9736 0.056 Uiso 1 1 calc R U . . .
C15 C 0.7111(7) 0.2377(6) 1.0454(6) 0.049(2) Uani 1 1 d D U . . .
H15A H 0.7834 0.2817 1.1017 0.058 Uiso 1 1 calc R U . . .
H15B H 0.7033 0.1600 1.0397 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6176(5) 0.2979(5) 1.0780(5) 0.0470(18) Uani 1 1 d . U . . .
C17 C 0.6179(7) 0.3501(9) 1.1834(6) 0.073(3) Uani 1 1 d . U . . .
H17 H 0.6796 0.3487 1.2386 0.087 Uiso 1 1 calc R U . . .
C18 C 0.5351(10) 0.4019(10) 1.2099(8) 0.125(7) Uani 1 1 d . U . . .
H18 H 0.5353 0.4377 1.2829 0.150 Uiso 1 1 calc R U . . .
C19 C 0.4419(8) 0.4022(9) 1.1217(8) 0.089(4) Uani 1 1 d . U . . .
H19 H 0.3794 0.4379 1.1356 0.107 Uiso 1 1 calc R U . . .
C20 C 0.4483(8) 0.3485(7) 1.0176(8) 0.069(3) Uani 1 1 d . U . . .
C21 C 0.3648(8) 0.3602(8) 0.9342(8) 0.059(2) Uani 1 1 d . U . . .
C22 C 0.2923(8) 0.3737(7) 0.8731(7) 0.057(2) Uani 1 1 d . U . . .
C23 C 0.1991(10) 0.3894(7) 0.7892(9) 0.059(3) Uani 1 1 d . U . . .
C24 C 0.2142(11) 0.3714(10) 0.7000(10) 0.071(3) Uani 1 1 d . U . . .
H24 H 0.2831 0.3508 0.6898 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1284(10) 0.3818(11) 0.6144(11) 0.078(3) Uani 1 1 d . U . . .
H25 H 0.1321 0.3610 0.5443 0.094 Uiso 1 1 calc R U . . .
C26 C 0.0347(12) 0.4290(13) 0.6517(13) 0.083(4) Uani 1 1 d . U . . .
H26 H -0.0173 0.4553 0.6086 0.099 Uiso 1 1 calc R U . . .
C27 C 0.0166(10) 0.4379(9) 0.7382(10) 0.062(3) Uani 1 1 d . U . . .
H27 H -0.0525 0.4573 0.7485 0.074 Uiso 1 1 calc R U . . .
C28 C 0.0981(10) 0.4193(8) 0.8170(10) 0.061(3) Uani 1 1 d . U . . .
H28 H 0.0881 0.4257 0.8812 0.073 Uiso 1 1 calc R U . . .
C29 C 0.7767(6) 0.1404(6) 0.8922(6) 0.050(2) Uani 1 1 d D U . . .
H29A H 0.8440 0.1455 0.9506 0.060 Uiso 1 1 calc R U . . .
H29B H 0.8015 0.1567 0.8413 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7122(8) 0.0203(8) 0.8324(5) 0.049(2) Uani 1 1 d . U . . .
C31 C 0.7636(8) -0.0746(9) 0.8112(8) 0.075(4) Uani 1 1 d . U . . .
H31 H 0.8426 -0.0680 0.8339 0.090 Uiso 1 1 calc R U . . .
C32 C 0.6917(10) -0.1882(9) 0.7515(9) 0.084(4) Uani 1 1 d . U . . .
H32 H 0.7226 -0.2576 0.7347 0.101 Uiso 1 1 calc R U . . .
C33 C 0.5831(8) -0.1893(8) 0.7226(8) 0.101(5) Uani 1 1 d . U . . .
H33 H 0.5362 -0.2621 0.6830 0.121 Uiso 1 1 calc R U . . .
C34 C 0.5324(8) -0.0914(7) 0.7463(7) 0.065(3) Uani 1 1 d . U . . .
C35 C 0.4134(8) -0.1029(8) 0.7366(9) 0.061(3) Uani 1 1 d . U . . .
C36 C 0.3253(8) -0.1267(8) 0.7325(10) 0.063(3) Uani 1 1 d . U . . .
C37 C 0.2167(9) -0.1540(10) 0.7379(11) 0.063(3) Uani 1 1 d . U . . .
C38 C 0.1859(9) -0.0748(9) 0.8207(10) 0.061(3) Uani 1 1 d . U . . .
H38 H 0.2307 -0.0019 0.8713 0.074 Uiso 1 1 calc R U . . .
C39 C 0.0870(11) -0.1061(12) 0.8272(14) 0.082(3) Uani 1 1 d . U . . .
H39 H 0.0642 -0.0521 0.8849 0.099 Uiso 1 1 calc R U . . .
C40 C 0.0195(9) -0.2072(9) 0.7583(11) 0.061(3) Uani 1 1 d . U . . .
H40 H -0.0467 -0.2245 0.7695 0.073 Uiso 1 1 calc R U . . .
C41 C 0.0486(10) -0.2879(12) 0.6684(14) 0.081(3) Uani 1 1 d . U . . .
H41 H 0.0000 -0.3573 0.6142 0.097 Uiso 1 1 calc R U . . .
C42 C 0.1518(8) -0.2602(9) 0.6634(10) 0.062(3) Uani 1 1 d . U . . .
H42 H 0.1779 -0.3145 0.6086 0.074 Uiso 1 1 calc R U . . .
C43 C 0.2995(5) 0.1119(9) 0.7250(5) 0.0287(13) Uani 1 1 d . U . . .
C44 C 0.1785(5) 0.0863(10) 0.6737(6) 0.0398(15) Uani 1 1 d . U . . .
H44A H 0.1439 0.0800 0.7231 0.060 Uiso 1 1 calc R U . . .
H44B H 0.1584 0.0133 0.6060 0.060 Uiso 1 1 calc R U . . .
H44C H 0.1520 0.1483 0.6577 0.060 Uiso 1 1 calc R U . . .
N1 N 0.6077(6) 0.2741(5) 0.7779(6) 0.0413(17) Uani 1 1 d . U . . .
N2 N 0.7095(4) 0.2273(5) 0.9401(4) 0.0362(12) Uani 1 1 d D U . . .
N3 N 0.5344(5) 0.2955(5) 0.9947(5) 0.0457(16) Uani 1 1 d . U . . .
N4 N 0.5986(6) 0.0173(6) 0.8032(5) 0.0395(18) Uani 1 1 d . U . . .
N5 N 0.3928(4) 0.1346(6) 0.7630(4) 0.0336(12) Uani 1 1 d . U . . .
O1 O 0.6258(5) 0.5482(7) 0.5968(4) 0.0583(14) Uani 1 1 d . U . . .
O2 O 0.6555(8) 0.4059(8) 0.4450(7) 0.087(3) Uani 1 1 d . U . . .
O3 O 0.7993(5) 0.5385(10) 0.5810(6) 0.0860(19) Uani 1 1 d . U . . .
O4 O 0.6581(8) 0.5934(9) 0.4683(8) 0.083(3) Uani 1 1 d . U . . .
O5 O 0.8763(8) 0.7961(10) 1.0912(7) 0.112(3) Uani 1 1 d . U . . .
O6 O 0.9752(9) 0.6645(8) 0.9953(10) 0.098(3) Uani 1 1 d . U . . .
O7 O 0.9641(10) 0.8408(10) 0.9999(11) 0.109(4) Uani 1 1 d . U . . .
O8 O 0.8170(8) 0.7015(13) 0.9063(7) 0.140(3) Uani 1 1 d . U . . .
Cl1 Cl 0.68768(16) 0.5203(3) 0.52051(15) 0.0535(6) Uani 1 1 d . U . . .
Cl2 Cl 0.90866(13) 0.7474(2) 0.99937(13) 0.0433(4) Uani 1 1 d . U . . .
Cu1 Cu 0.55079(6) 0.17676(9) 0.84627(6) 0.0321(3) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.293(12) . ?
C1 C2 1.428(14) . ?
C1 C14 1.469(13) . ?
C2 C3 1.259(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(13) . ?
C4 H4 0.9500 . ?
C5 N1 1.369(11) . ?
C5 C6 1.402(12) . ?
C6 C7 1.199(11) . ?
C7 C8 1.477(13) . ?
C8 C9 1.384(11) . ?
C8 C13 1.397(14) . ?
C9 C10 1.397(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.441(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.339(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.485(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N2 1.474(7) . ?
C15 C16 1.504(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.342(9) . ?
C16 C17 1.373(11) . ?
C17 C18 1.314(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.471(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(14) . ?
C19 H19 0.9500 . ?
C20 N3 1.343(11) . ?
C20 C21 1.427(13) . ?
C21 C22 1.155(12) . ?
C22 C23 1.523(14) . ?
C23 C24 1.287(17) . ?
C23 C28 1.459(17) . ?
C24 C25 1.455(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.476(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.302(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.417(15) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N2 1.470(7) . ?
C29 C30 1.504(12) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.361(14) . ?
C30 N4 1.375(12) . ?
C31 C32 1.478(15) . ?
C31 H31 0.9500 . ?
C32 C33 1.317(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(14) . ?
C33 H33 0.9500 . ?
C34 N4 1.400(11) . ?
C34 C35 1.477(13) . ?
C35 C36 1.140(13) . ?
C36 C37 1.459(14) . ?
C37 C38 1.358(15) . ?
C37 C42 1.384(15) . ?
C38 C39 1.365(16) . ?
C38 H38 0.9500 . ?
C39 C40 1.342(18) . ?
C39 H39 0.9500 . ?
C40 C41 1.421(19) . ?
C40 H40 0.9500 . ?
C41 C42 1.392(15) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 N5 1.125(8) . ?
C43 C44 1.459(8) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
N1 Cu1 2.176(7) . ?
N2 Cu1 1.983(5) . ?
N3 Cu1 2.097(7) . ?
N4 Cu1 2.050(7) . ?
N5 Cu1 1.941(5) . ?
O1 Cl1 1.464(6) . ?
O2 Cl1 1.373(8) . ?
O3 Cl1 1.385(6) . ?
O4 Cl1 1.464(9) . ?
O5 Cl2 1.388(8) . ?
O6 Cl2 1.371(9) . ?
O7 Cl2 1.412(11) . ?
O8 Cl2 1.376(7) . ?

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 119.1(9) . . ?
N1 C1 C14 120.6(9) . . ?
C2 C1 C14 120.3(8) . . ?
C3 C2 C1 121.5(10) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 123.3(11) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 113.9(10) . . ?
C3 C4 H4 123.0 . . ?
C5 C4 H4 123.0 . . ?
N1 C5 C6 118.2(8) . . ?
N1 C5 C4 122.0(8) . . ?
C6 C5 C4 119.7(9) . . ?
C7 C6 C5 177.2(10) . . ?
C6 C7 C8 176.5(10) . . ?
C9 C8 C13 125.9(11) . . ?
C9 C8 C7 113.5(10) . . ?
C13 C8 C7 120.6(9) . . ?
C8 C9 C10 113.6(11) . . ?
C8 C9 H9 123.2 . . ?
C10 C9 H9 123.2 . . ?
C11 C10 C9 127.9(10) . . ?
C11 C10 H10 116.1 . . ?
C9 C10 H10 116.1 . . ?
C10 C11 C12 109.2(11) . . ?
C10 C11 H11 125.4 . . ?
C12 C11 H11 125.4 . . ?
C13 C12 C11 128.9(13) . . ?
C13 C12 H12 115.6 . . ?
C11 C12 H12 115.6 . . ?
C12 C13 C8 113.1(10) . . ?
C12 C13 H13 123.4 . . ?
C8 C13 H13 123.4 . . ?
C1 C14 N2 108.9(6) . . ?
C1 C14 H14A 109.9 . . ?
N2 C14 H14A 109.9 . . ?
C1 C14 H14B 109.9 . . ?
N2 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
N2 C15 C16 110.4(5) . . ?
N2 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C17 123.5(7) . . ?
N3 C16 C15 113.8(6) . . ?
C17 C16 C15 122.7(7) . . ?
C18 C17 C16 121.6(8) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 117.1(9) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
C20 C19 C18 117.8(9) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
N3 C20 C19 122.7(8) . . ?
N3 C20 C21 119.1(8) . . ?
C19 C20 C21 117.9(9) . . ?
C22 C21 C20 174.0(11) . . ?
C21 C22 C23 177.6(11) . . ?
C24 C23 C28 126.2(10) . . ?
C24 C23 C22 118.1(11) . . ?
C28 C23 C22 115.6(11) . . ?
C23 C24 C25 121.6(13) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 110.6(12) . . ?
C24 C25 H25 124.7 . . ?
C26 C25 H25 124.7 . . ?
C27 C26 C25 126.1(11) . . ?
C27 C26 H26 117.0 . . ?
C25 C26 H26 117.0 . . ?
C26 C27 C28 121.2(13) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C27 C28 C23 112.9(11) . . ?
C27 C28 H28 123.5 . . ?
C23 C28 H28 123.5 . . ?
N2 C29 C30 111.8(6) . . ?
N2 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
N2 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 N4 124.4(8) . . ?
C31 C30 C29 122.1(8) . . ?
N4 C30 C29 113.5(7) . . ?
C30 C31 C32 117.4(9) . . ?
C30 C31 H31 121.3 . . ?
C32 C31 H31 121.3 . . ?
C33 C32 C31 117.3(9) . . ?
C33 C32 H32 121.4 . . ?
C31 C32 H32 121.4 . . ?
C32 C33 C34 124.4(9) . . ?
C32 C33 H33 117.8 . . ?
C34 C33 H33 117.8 . . ?
C33 C34 N4 119.5(8) . . ?
C33 C34 C35 118.0(8) . . ?
N4 C34 C35 120.6(8) . . ?
C36 C35 C34 168.7(11) . . ?
C35 C36 C37 174.8(13) . . ?
C38 C37 C42 122.5(10) . . ?
C38 C37 C36 117.7(10) . . ?
C42 C37 C36 119.8(11) . . ?
C37 C38 C39 116.1(12) . . ?
C37 C38 H38 121.9 . . ?
C39 C38 H38 121.9 . . ?
C40 C39 C38 125.0(14) . . ?
C40 C39 H39 117.5 . . ?
C38 C39 H39 117.5 . . ?
C39 C40 C41 119.0(11) . . ?
C39 C40 H40 120.5 . . ?
C41 C40 H40 120.5 . . ?
C42 C41 C40 116.8(12) . . ?
C42 C41 H41 121.6 . . ?
C40 C41 H41 121.6 . . ?
C37 C42 C41 120.4(11) . . ?
C37 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
N5 C43 C44 177.4(12) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C1 N1 C5 120.1(8) . . ?
C1 N1 Cu1 108.3(7) . . ?
C5 N1 Cu1 131.5(6) . . ?
C29 N2 C15 110.6(4) . . ?
C29 N2 C14 110.7(4) . . ?
C15 N2 C14 111.0(4) . . ?
C29 N2 Cu1 109.9(4) . . ?
C15 N2 Cu1 105.3(4) . . ?
C14 N2 Cu1 109.2(4) . . ?
C20 N3 C16 117.3(7) . . ?
C20 N3 Cu1 131.0(5) . . ?
C16 N3 Cu1 110.3(5) . . ?
C30 N4 C34 117.1(7) . . ?
C30 N4 Cu1 113.7(6) . . ?
C34 N4 Cu1 129.2(6) . . ?
C43 N5 Cu1 172.5(6) . . ?
O2 Cl1 O3 109.3(6) . . ?
O2 Cl1 O4 110.6(6) . . ?
O3 Cl1 O4 115.0(7) . . ?
O2 Cl1 O1 108.7(6) . . ?
O3 Cl1 O1 106.4(4) . . ?
O4 Cl1 O1 106.5(6) . . ?
O6 Cl2 O8 108.8(8) . . ?
O6 Cl2 O5 114.6(8) . . ?
O8 Cl2 O5 110.8(7) . . ?
O6 Cl2 O7 111.2(5) . . ?
O8 Cl2 O7 105.9(8) . . ?
O5 Cl2 O7 105.1(8) . . ?
N5 Cu1 N2 176.1(2) . . ?
N5 Cu1 N4 100.9(3) . . ?
N2 Cu1 N4 81.8(3) . . ?
N5 Cu1 N3 96.7(2) . . ?
N2 Cu1 N3 79.4(2) . . ?
N4 Cu1 N3 129.0(3) . . ?
N5 Cu1 N1 101.3(3) . . ?
N2 Cu1 N1 80.0(3) . . ?
N4 Cu1 N1 115.0(2) . . ?
N3 Cu1 N1 107.7(3) . . ?

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 -0.2(4) . . . . ?
C14 C1 C2 C3 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 N1 1.6(7) . . . . ?
C3 C4 C5 C6 -176.7(8) . . . . ?
C13 C8 C9 C10 3(2) . . . . ?
C7 C8 C9 C10 180.0(7) . . . . ?
C8 C9 C10 C11 -4.9(19) . . . . ?
C9 C10 C11 C12 9.6(18) . . . . ?
C10 C11 C12 C13 -15(2) . . . . ?
C11 C12 C13 C8 13(2) . . . . ?
C9 C8 C13 C12 -6.4(19) . . . . ?
C7 C8 C13 C12 176.5(10) . . . . ?
N1 C1 C14 N2 24.1(5) . . . . ?
C2 C1 C14 N2 -156.5(5) . . . . ?
N2 C15 C16 N3 20.5(5) . . . . ?
N2 C15 C16 C17 -159.7(5) . . . . ?
N3 C16 C17 C18 0.0(4) . . . . ?
C15 C16 C17 C18 -179.8(3) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C18 C19 C20 N3 1.1(8) . . . . ?
C18 C19 C20 C21 -172.7(9) . . . . ?
C28 C23 C24 C25 1.2(18) . . . . ?
C22 C23 C24 C25 178.5(10) . . . . ?
C23 C24 C25 C26 7.5(17) . . . . ?
C24 C25 C26 C27 -14(2) . . . . ?
C25 C26 C27 C28 11(2) . . . . ?
C26 C27 C28 C23 -0.5(15) . . . . ?
C24 C23 C28 C27 -5.4(15) . . . . ?
C22 C23 C28 C27 177.3(8) . . . . ?
N2 C29 C30 C31 -159.0(5) . . . . ?
N2 C29 C30 N4 20.5(5) . . . . ?
N4 C30 C31 C32 0.8(4) . . . . ?
C29 C30 C31 C32 -179.8(2) . . . . ?
C30 C31 C32 C33 0.4(5) . . . . ?
C31 C32 C33 C34 -1.3(8) . . . . ?
C32 C33 C34 N4 0.9(8) . . . . ?
C32 C33 C34 C35 -163.2(9) . . . . ?
C33 C34 C35 C36 27(7) . . . . ?
N4 C34 C35 C36 -137(6) . . . . ?
C42 C37 C38 C39 0.4(18) . . . . ?
C36 C37 C38 C39 -176.0(11) . . . . ?
C37 C38 C39 C40 -0.4(19) . . . . ?
C38 C39 C40 C41 -3(2) . . . . ?
C39 C40 C41 C42 5.7(18) . . . . ?
C38 C37 C42 C41 2.9(19) . . . . ?
C36 C37 C42 C41 179.2(12) . . . . ?
C40 C41 C42 C37 -5.8(19) . . . . ?
C2 C1 N1 C5 1.6(5) . . . . ?
C14 C1 N1 C5 -179.0(3) . . . . ?
C2 C1 N1 Cu1 -178.3(4) . . . . ?
C14 C1 N1 Cu1 1.1(4) . . . . ?
C6 C5 N1 C1 176.0(7) . . . . ?
C4 C5 N1 C1 -2.3(7) . . . . ?
C6 C5 N1 Cu1 -4.2(8) . . . . ?
C4 C5 N1 Cu1 177.5(5) . . . . ?
C30 C29 N2 C15 82.9(6) . . . . ?
C30 C29 N2 C14 -153.6(5) . . . . ?
C30 C29 N2 Cu1 -32.9(5) . . . . ?
C16 C15 N2 C29 -163.1(5) . . . . ?
C16 C15 N2 C14 73.6(6) . . . . ?
C16 C15 N2 Cu1 -44.4(5) . . . . ?
C1 C14 N2 C29 82.9(6) . . . . ?
C1 C14 N2 C15 -153.9(5) . . . . ?
C1 C14 N2 Cu1 -38.3(4) . . . . ?
C19 C20 N3 C16 -1.4(7) . . . . ?
C21 C20 N3 C16 172.4(8) . . . . ?
C19 C20 N3 Cu1 163.6(6) . . . . ?
C21 C20 N3 Cu1 -22.6(10) . . . . ?
C17 C16 N3 C20 0.9(5) . . . . ?
C15 C16 N3 C20 -179.4(3) . . . . ?
C17 C16 N3 Cu1 -167.1(4) . . . . ?
C15 C16 N3 Cu1 12.6(4) . . . . ?
C31 C30 N4 C34 -1.1(5) . . . . ?
C29 C30 N4 C34 179.4(3) . . . . ?
C31 C30 N4 Cu1 -179.1(4) . . . . ?
C29 C30 N4 Cu1 1.4(4) . . . . ?
C33 C34 N4 C30 0.3(7) . . . . ?
C35 C34 N4 C30 164.0(8) . . . . ?
C33 C34 N4 Cu1 177.9(5) . . . . ?
C35 C34 N4 Cu1 -18.4(10) . . . . ?

_refine_diff_density_max         0.800
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1028490'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N4, Cu 2+, 2 Cl O4 1-, C H4 O'
_chemical_formula_sum            'C27 H26 Cl2 Cu N4 O9'
_chemical_formula_weight         684.96

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.9021(8)
_cell_length_b                   22.0571(19)
_cell_length_c                   12.5252(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.189(8)
_cell_angle_gamma                90
_cell_volume                     2892.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7078
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      25.4

_exptl_crystal_description       prisms
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.000
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova X-ray source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at 0, AtlasS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28259
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.450
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6631
_reflns_number_gt                4878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_refine_special_details          
;
 One of the perchlorate ions was disordered over two orientations.  The disorder 
was modeled by assigning the variable x to the site occupancy factors for one 
component of the disorder.  The variable (1-x) was assigned to the site 
occupancy factors for the alternate component.  The isotropic displacement 
parameters for the chlorine atoms and for the oxygen atoms were refined while 
refining the variable x.  Constraints were applied so that the isotropic 
displacement parameters for the chlorine atoms were kept equal.  Similar constraints 
were applied to the displacement parameters for the oxygen atoms.  The geometry of 
the two ions were restrained to be equivalent throughout the refinement 
procedure.  In this way, the site occupancy for the major component consisting of 
atoms, Cl1, O1, O2, O3 and O4 refined to 60(2)%.  The atoms of this disordered ion 
were ultimately refined anisotropically with their displacement parameters 
restrained to be approximately isotropic.
	The hydrogen atom on the methanolic oxygen atom was initially located in a 
difference electron density map.  However, this hydrogen was refined tied to the 
oxygen atom in the final refinement model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+7.1065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6631
_refine_ls_number_parameters     440
_refine_ls_number_restraints     645
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2361
_refine_ls_wR_factor_gt          0.2166
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.124
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3505(4) 0.8062(2) 0.5836(4) 0.0419(10) Uani 1 1 d . U . . .
H1 H 0.2766 0.7814 0.5590 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3359(5) 0.8666(2) 0.6033(4) 0.0469(11) Uani 1 1 d . U . . .
H2 H 0.2529 0.8836 0.5906 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4420(6) 0.9022(3) 0.6412(4) 0.0540(13) Uani 1 1 d . U . . .
H3 H 0.4338 0.9438 0.6576 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5604(6) 0.8769(3) 0.6552(5) 0.0560(13) Uani 1 1 d . U . . .
H4 H 0.6353 0.9010 0.6801 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5691(5) 0.8166(3) 0.6327(5) 0.0500(12) Uani 1 1 d . U . . .
C6 C 0.6945(6) 0.7846(3) 0.6493(6) 0.0694(17) Uani 1 1 d . U . . .
H6A H 0.7579 0.8125 0.6326 0.083 Uiso 1 1 calc R U . . .
H6B H 0.7272 0.7712 0.7276 0.083 Uiso 1 1 calc R U . . .
C7 C 0.7779(7) 0.6853(4) 0.6150(8) 0.092(3) Uani 1 1 d . U . . .
H7A H 0.7890 0.6609 0.5520 0.111 Uiso 1 1 calc R U . . .
H7B H 0.8595 0.7063 0.6499 0.111 Uiso 1 1 calc R U . . .
C8 C 0.7453(8) 0.6447(4) 0.6977(6) 0.084(2) Uani 1 1 d . U . . .
C9 C 0.8439(10) 0.6153(5) 0.7845(8) 0.113(3) Uani 1 1 d . U . . .
H9 H 0.9325 0.6230 0.7974 0.136 Uiso 1 1 calc R U . . .
C10 C 0.7950(12) 0.5743(5) 0.8471(8) 0.110(3) Uani 1 1 d . U . . .
H10 H 0.8561 0.5528 0.9033 0.131 Uiso 1 1 calc R U . . .
C11 C 0.6751(13) 0.5619(4) 0.8377(7) 0.117(3) Uani 1 1 d . U . . .
H11 H 0.6494 0.5335 0.8843 0.141 Uiso 1 1 calc R U . . .
C12 C 0.5879(10) 0.5939(3) 0.7536(6) 0.091(2) Uani 1 1 d . U . . .
H12 H 0.4993 0.5871 0.7427 0.109 Uiso 1 1 calc R U . . .
C13 C 0.6609(6) 0.7501(3) 0.4568(6) 0.0685(17) Uani 1 1 d . U . . .
H13A H 0.7465 0.7571 0.4462 0.082 Uiso 1 1 calc R U . . .
H13B H 0.6129 0.7887 0.4421 0.082 Uiso 1 1 calc R U . . .
C14 C 0.5923(5) 0.7031(2) 0.3771(5) 0.0484(12) Uani 1 1 d . U . . .
C15 C 0.6038(5) 0.6987(3) 0.2710(5) 0.0567(14) Uani 1 1 d . U . . .
H15 H 0.6587 0.7255 0.2468 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5359(5) 0.6555(3) 0.1999(4) 0.0505(12) Uani 1 1 d . U . . .
H16 H 0.5407 0.6530 0.1255 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4611(4) 0.6159(2) 0.2382(4) 0.0442(11) Uani 1 1 d . U . . .
H17 H 0.4159 0.5847 0.1911 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4516(4) 0.6215(2) 0.3457(4) 0.0376(9) Uani 1 1 d . U . . .
C19 C 0.3772(5) 0.5799(2) 0.3891(4) 0.0404(10) Uani 1 1 d . U . . .
C20 C 0.3157(5) 0.54422(19) 0.4232(4) 0.0423(10) Uani 1 1 d . U . . .
C21 C 0.2410(5) 0.50224(19) 0.4674(4) 0.0412(10) Uani 1 1 d . U . . .
C22 C 0.2845(6) 0.4850(2) 0.5790(5) 0.0548(13) Uani 1 1 d . U . . .
H22 H 0.3635 0.5001 0.6242 0.066 Uiso 1 1 calc R U . . .
C23 C 0.2132(7) 0.4461(3) 0.6236(6) 0.0676(17) Uani 1 1 d . U . . .
H23 H 0.2427 0.4344 0.6995 0.081 Uiso 1 1 calc R U . . .
C24 C 0.0997(7) 0.4244(3) 0.5580(7) 0.0706(18) Uani 1 1 d . U . . .
H24 H 0.0505 0.3977 0.5891 0.085 Uiso 1 1 calc R U . . .
C25 C 0.0548(6) 0.4406(3) 0.4469(6) 0.0658(16) Uani 1 1 d . U . . .
H25 H -0.0235 0.4244 0.4022 0.079 Uiso 1 1 calc R U . . .
C26 C 0.1250(5) 0.4806(2) 0.4013(5) 0.0521(13) Uani 1 1 d . U . . .
H26 H 0.0940 0.4929 0.3259 0.063 Uiso 1 1 calc R U . . .
C27 C 0.2907(8) 0.6582(3) 0.6777(6) 0.0784(19) Uani 1 1 d . U . . .
H27A H 0.3492 0.6787 0.7413 0.118 Uiso 1 1 calc R U . . .
H27B H 0.2797 0.6159 0.6971 0.118 Uiso 1 1 calc R U . . .
H27C H 0.2077 0.6788 0.6587 0.118 Uiso 1 1 calc R U . . .
N1 N 0.4658(4) 0.78099(18) 0.5982(3) 0.0393(8) Uani 1 1 d . U . . .
N2 N 0.6749(4) 0.7308(2) 0.5734(5) 0.0643(13) Uani 1 1 d . U . . .
N3 N 0.6247(7) 0.6342(3) 0.6869(4) 0.0777(17) Uani 1 1 d . U . . .
N4 N 0.5155(4) 0.66558(18) 0.4155(3) 0.0420(9) Uani 1 1 d . U . . .
Cl1 Cl 0.7500(3) 0.43347(13) 1.0844(2) 0.0574(7) Uani 0.6 1 d D U P A 1
O1 O 0.8536(8) 0.4213(5) 1.1768(6) 0.125(3) Uani 0.6 1 d D U P A 1
O2 O 0.6768(10) 0.4814(4) 1.1124(9) 0.147(4) Uani 0.6 1 d D U P A 1
O3 O 0.6720(9) 0.3827(4) 1.0517(8) 0.129(4) Uani 0.6 1 d D U P A 1
O4 O 0.7952(10) 0.4538(4) 0.9946(6) 0.112(3) Uani 0.6 1 d D U P A 1
Cl1A Cl 0.8141(6) 0.4254(2) 1.0864(4) 0.0790(15) Uani 0.4 1 d D U P B 2
O1A O 0.7229(10) 0.4049(5) 0.9910(7) 0.091(3) Uani 0.4 1 d D U P B 2
O2A O 0.9122(10) 0.4569(5) 1.0560(9) 0.098(3) Uani 0.4 1 d D U P B 2
O3A O 0.7596(12) 0.4653(5) 1.1494(9) 0.102(4) Uani 0.4 1 d D U P B 2
O4A O 0.8658(11) 0.3752(4) 1.1545(8) 0.085(3) Uani 0.4 1 d D U P B 2
O5 O 0.0444(4) 0.7423(2) 0.5216(3) 0.0723(12) Uani 1 1 d D U . . .
O6 O -0.0814(3) 0.71584(18) 0.3464(3) 0.0569(9) Uani 1 1 d D U . . .
O7 O 0.0857(5) 0.7828(2) 0.3641(5) 0.106(2) Uani 1 1 d D U . . .
O8 O 0.1281(4) 0.68247(19) 0.4090(4) 0.0721(12) Uani 1 1 d D U . . .
O9 O 0.3430(4) 0.66020(19) 0.5831(3) 0.0606(10) Uani 1 1 d G U . . .
H9O H 0.2884 0.6609 0.5207 0.091 Uiso 1 1 d G U . . .
Cu1 Cu 0.50985(6) 0.69317(3) 0.57999(5) 0.0489(2) Uani 1 1 d . U . . .
Cl2 Cl 0.04291(11) 0.73165(5) 0.41095(10) 0.0472(3) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(6) . ?
C1 C2 1.374(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.343(6) . ?
C5 C6 1.500(8) . ?
C6 N2 1.498(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.484(13) . ?
C7 N2 1.489(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.305(10) . ?
C8 C9 1.452(11) . ?
C9 C10 1.397(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.307(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(12) . ?
C11 H11 0.9500 . ?
C12 N3 1.355(11) . ?
C12 H12 0.9500 . ?
C13 N2 1.487(9) . ?
C13 C14 1.488(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.358(6) . ?
C14 C15 1.372(8) . ?
C15 C16 1.371(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(7) . ?
C17 H17 0.9500 . ?
C18 N4 1.363(6) . ?
C18 C19 1.429(6) . ?
C19 C20 1.188(7) . ?
C20 C21 1.442(6) . ?
C21 C26 1.389(8) . ?
C21 C22 1.398(7) . ?
C22 C23 1.376(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.367(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O9 1.452(8) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N1 Cu1 2.024(4) . ?
N2 Cu1 2.004(5) . ?
N3 Cu1 2.030(5) . ?
N4 Cu1 2.165(4) . ?
Cl1 O3 1.396(6) . ?
Cl1 O1 1.399(5) . ?
Cl1 O4 1.420(5) . ?
Cl1 O2 1.427(6) . ?
Cl1A O1A 1.399(6) . ?
Cl1A O2A 1.413(6) . ?
Cl1A O4A 1.416(6) . ?
Cl1A O3A 1.420(6) . ?
O5 Cl2 1.402(4) . ?
O6 Cl2 1.414(3) . ?
O7 Cl2 1.411(4) . ?
O8 Cl2 1.433(4) . ?
O9 H9O 0.8400 . ?

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 122.0(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 C6 114.8(5) . . ?
C4 C5 C6 122.8(5) . . ?
N2 C6 C5 108.8(5) . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 N2 110.3(6) . . ?
C8 C7 H7A 109.6 . . ?
N2 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 C9 120.7(10) . . ?
N3 C8 C7 117.8(6) . . ?
C9 C8 C7 121.4(9) . . ?
C10 C9 C8 113.1(10) . . ?
C10 C9 H9 123.5 . . ?
C8 C9 H9 123.5 . . ?
C11 C10 C9 127.8(10) . . ?
C11 C10 H10 116.1 . . ?
C9 C10 H10 116.1 . . ?
C10 C11 C12 114.6(12) . . ?
C10 C11 H11 122.7 . . ?
C12 C11 H11 122.7 . . ?
N3 C12 C11 122.7(10) . . ?
N3 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N2 C13 C14 110.8(5) . . ?
N2 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N4 C14 C15 122.1(5) . . ?
N4 C14 C13 115.5(5) . . ?
C15 C14 C13 122.4(5) . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 118.8(5) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
N4 C18 C17 121.6(4) . . ?
N4 C18 C19 117.1(4) . . ?
C17 C18 C19 121.2(4) . . ?
C20 C19 C18 178.2(5) . . ?
C19 C20 C21 178.1(5) . . ?
C26 C21 C22 120.0(5) . . ?
C26 C21 C20 120.7(5) . . ?
C22 C21 C20 119.3(5) . . ?
C23 C22 C21 120.2(6) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.5(6) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.4(6) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 119.6(6) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 119.2(6) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1 N1 C5 118.2(4) . . ?
C1 N1 Cu1 128.6(3) . . ?
C5 N1 Cu1 113.1(3) . . ?
C13 N2 C7 113.4(5) . . ?
C13 N2 C6 110.8(6) . . ?
C7 N2 C6 110.6(5) . . ?
C13 N2 Cu1 108.1(3) . . ?
C7 N2 Cu1 107.7(5) . . ?
C6 N2 Cu1 105.8(3) . . ?
C8 N3 C12 121.1(7) . . ?
C8 N3 Cu1 111.9(6) . . ?
C12 N3 Cu1 126.4(6) . . ?
C14 N4 C18 117.5(4) . . ?
C14 N4 Cu1 110.5(3) . . ?
C18 N4 Cu1 131.8(3) . . ?
O3 Cl1 O1 112.0(5) . . ?
O3 Cl1 O4 109.8(5) . . ?
O1 Cl1 O4 109.7(5) . . ?
O3 Cl1 O2 109.2(5) . . ?
O1 Cl1 O2 108.5(5) . . ?
O4 Cl1 O2 107.6(5) . . ?
O1A Cl1A O2A 109.9(5) . . ?
O1A Cl1A O4A 109.3(5) . . ?
O2A Cl1A O4A 110.1(5) . . ?
O1A Cl1A O3A 111.5(5) . . ?
O2A Cl1A O3A 108.0(5) . . ?
O4A Cl1A O3A 107.9(5) . . ?
C27 O9 H9O 115.0 . . ?
N2 Cu1 N1 81.48(18) . . ?
N2 Cu1 N3 84.1(3) . . ?
N1 Cu1 N3 131.41(18) . . ?
N2 Cu1 N4 79.23(18) . . ?
N1 Cu1 N4 116.53(15) . . ?
N3 Cu1 N4 105.76(18) . . ?
O5 Cl2 O7 111.3(3) . . ?
O5 Cl2 O6 110.6(2) . . ?
O7 Cl2 O6 109.6(3) . . ?
O5 Cl2 O8 108.4(2) . . ?
O7 Cl2 O8 107.9(3) . . ?
O6 Cl2 O8 109.0(2) . . ?

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 -1.5(7) . . . . ?
C1 C2 C3 C4 2.1(7) . . . . ?
C2 C3 C4 C5 -1.2(8) . . . . ?
C3 C4 C5 N1 -0.5(9) . . . . ?
C3 C4 C5 C6 -177.8(6) . . . . ?
N1 C5 C6 N2 27.7(8) . . . . ?
C4 C5 C6 N2 -154.9(6) . . . . ?
N2 C7 C8 N3 30.2(8) . . . . ?
N2 C7 C8 C9 -152.8(6) . . . . ?
N3 C8 C9 C10 3.0(9) . . . . ?
C7 C8 C9 C10 -173.9(6) . . . . ?
C8 C9 C10 C11 -2.2(12) . . . . ?
C9 C10 C11 C12 0.6(13) . . . . ?
C10 C11 C12 N3 0.3(11) . . . . ?
N2 C13 C14 N4 24.0(7) . . . . ?
N2 C13 C14 C15 -157.2(5) . . . . ?
N4 C14 C15 C16 0.3(8) . . . . ?
C13 C14 C15 C16 -178.3(6) . . . . ?
C14 C15 C16 C17 -2.4(8) . . . . ?
C15 C16 C17 C18 2.3(7) . . . . ?
C16 C17 C18 N4 -0.2(7) . . . . ?
C16 C17 C18 C19 -178.3(4) . . . . ?
C26 C21 C22 C23 0.5(7) . . . . ?
C20 C21 C22 C23 178.5(5) . . . . ?
C21 C22 C23 C24 0.1(8) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
C23 C24 C25 C26 -1.3(9) . . . . ?
C22 C21 C26 C25 -1.5(7) . . . . ?
C20 C21 C26 C25 -179.4(4) . . . . ?
C24 C25 C26 C21 1.9(7) . . . . ?
C2 C1 N1 C5 -0.2(7) . . . . ?
C2 C1 N1 Cu1 177.5(3) . . . . ?
C4 C5 N1 C1 1.2(8) . . . . ?
C6 C5 N1 C1 178.7(5) . . . . ?
C4 C5 N1 Cu1 -176.8(5) . . . . ?
C6 C5 N1 Cu1 0.6(6) . . . . ?
C14 C13 N2 C7 77.4(7) . . . . ?
C14 C13 N2 C6 -157.5(5) . . . . ?
C14 C13 N2 Cu1 -42.0(6) . . . . ?
C8 C7 N2 C13 -149.3(6) . . . . ?
C8 C7 N2 C6 85.5(7) . . . . ?
C8 C7 N2 Cu1 -29.7(7) . . . . ?
C5 C6 N2 C13 75.3(6) . . . . ?
C5 C6 N2 C7 -158.1(6) . . . . ?
C5 C6 N2 Cu1 -41.7(6) . . . . ?
C9 C8 N3 C12 -2.4(9) . . . . ?
C7 C8 N3 C12 174.6(6) . . . . ?
C9 C8 N3 Cu1 168.8(5) . . . . ?
C7 C8 N3 Cu1 -14.2(7) . . . . ?
C11 C12 N3 C8 0.7(10) . . . . ?
C11 C12 N3 Cu1 -169.2(5) . . . . ?
C15 C14 N4 C18 1.8(7) . . . . ?
C13 C14 N4 C18 -179.4(5) . . . . ?
C15 C14 N4 Cu1 -174.3(4) . . . . ?
C13 C14 N4 Cu1 4.4(6) . . . . ?
C17 C18 N4 C14 -1.9(6) . . . . ?
C19 C18 N4 C14 176.3(4) . . . . ?
C17 C18 N4 Cu1 173.3(3) . . . . ?
C19 C18 N4 Cu1 -8.5(6) . . . . ?

_refine_diff_density_max         1.559
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4

