# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_HL
_database_code_depnum_ccdc_archive 'CCDC 1425680'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N4 O'
_chemical_formula_weight         384.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   14.0046(13)
_cell_length_b                   8.9892(8)
_cell_length_c                   16.6000(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.069(2)
_cell_angle_gamma                90.00
_cell_volume                     2017.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1488
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      22.14

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13382
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4650
_reflns_number_gt                2259
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0672P)²+1.1850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.2045
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85459(14) 0.4227(2) 0.51399(15) 0.0612(7) Uani 1 1 d . A 1
H1 H 0.8456(7) 0.327(4) 0.513(2) 0.092 Uiso 1 1 calc R A 1
N1A N 0.8148(3) 1.1250(5) 0.5272(3) 0.0447(11) Uani 0.662(4) 1 d P B 1
N2A N 0.8418(3) 0.8814(4) 0.5471(3) 0.0360(9) Uani 0.662(4) 1 d P B 1
N3A N 0.9322(2) 0.7366(4) 0.4754(2) 0.0461(11) Uani 0.662(4) 1 d P B 1
H3C H 0.9820 0.6703 0.4844 0.055 Uiso 0.662(4) 1 d PR B 1
N4 N 0.50895(19) 0.3966(3) 0.3740(2) 0.0814(10) Uani 1 1 d . . .
C1A C 0.7873(3) 1.0802(7) 0.5973(2) 0.0457(14) Uani 0.662(4) 1 d PG B 1
C2A C 0.7519(5) 1.1625(5) 0.6543(4) 0.061(2) Uani 0.662(4) 1 d PG B 1
H2A H 0.7405 1.2640 0.6461 0.073 Uiso 0.662(4) 1 calc PR B 1
C3A C 0.7334(7) 1.0932(8) 0.7235(4) 0.075(3) Uani 0.662(4) 1 d PG B 1
H3A H 0.7096 1.1482 0.7616 0.091 Uiso 0.662(4) 1 calc PR B 1
C4A C 0.7503(7) 0.9415(8) 0.7358(3) 0.061(2) Uani 0.662(4) 1 d PG B 1
H4A H 0.7380 0.8951 0.7822 0.073 Uiso 0.662(4) 1 calc PR B 1
C5A C 0.7858(5) 0.8592(5) 0.6789(4) 0.0503(18) Uani 0.662(4) 1 d PG B 1
H5A H 0.7972 0.7577 0.6871 0.060 Uiso 0.662(4) 1 calc PR B 1
C6A C 0.8043(3) 0.9285(6) 0.6096(3) 0.0390(15) Uani 0.662(4) 1 d PG B 1
C7A C 0.8471(6) 0.9995(10) 0.4981(5) 0.0349(18) Uani 0.662(4) 1 d P B 1
C8A C 0.8827(3) 0.9818(9) 0.4259(2) 0.0407(16) Uani 0.662(4) 1 d PG B 1
C9A C 0.8807(4) 1.0978(6) 0.3701(5) 0.0527(18) Uani 0.662(4) 1 d PG B 1
H9A H 0.8515 1.1879 0.3773 0.063 Uiso 0.662(4) 1 calc PR B 1
C10A C 0.9226(7) 1.0790(7) 0.3034(4) 0.063(2) Uani 0.662(4) 1 d PG B 1
H10A H 0.9213 1.1566 0.2661 0.076 Uiso 0.662(4) 1 calc PR B 1
C11A C 0.9663(6) 0.9443(9) 0.2926(4) 0.071(3) Uani 0.662(4) 1 d PG B 1
H11A H 0.9943 0.9317 0.2480 0.085 Uiso 0.662(4) 1 calc PR B 1
C12A C 0.9683(4) 0.8283(5) 0.3484(5) 0.0547(17) Uani 0.662(4) 1 d PG B 1
H12A H 0.9975 0.7382 0.3411 0.066 Uiso 0.662(4) 1 calc PR B 1
C13A C 0.9264(4) 0.8471(6) 0.4150(3) 0.0424(15) Uani 0.662(4) 1 d PG B 1
C14A C 0.8584(3) 0.7275(4) 0.5248(3) 0.0401(11) Uani 0.662(4) 1 d P B 1
H14A H 0.8887 0.6735 0.5764 0.048 Uiso 0.662(4) 1 calc PR B 1
C15 C 0.76540(19) 0.6466(3) 0.48096(16) 0.0377(6) Uani 1 1 d . . .
C16 C 0.6756(2) 0.7142(3) 0.44450(19) 0.0492(8) Uani 1 1 d . B .
H16 H 0.6725 0.8176 0.4445 0.059 Uiso 1 1 calc R . .
C17 C 0.5913(2) 0.6363(3) 0.40848(19) 0.0547(8) Uani 1 1 d . . .
H17 H 0.5331 0.6873 0.3844 0.066 Uiso 1 1 calc R B .
C18 C 0.5921(2) 0.4798(3) 0.40761(19) 0.0506(8) Uani 1 1 d . B .
C19 C 0.6828(2) 0.4105(3) 0.44205(19) 0.0495(8) Uani 1 1 d . . .
H19 H 0.6869 0.3073 0.4405 0.059 Uiso 1 1 calc R B .
C20 C 0.76674(19) 0.4919(3) 0.47837(17) 0.0405(6) Uani 1 1 d . A .
C21 C 0.4079(3) 0.4572(5) 0.3612(3) 0.0891(13) Uani 1 1 d . . .
H21A H 0.3676 0.3874 0.3825 0.107 Uiso 1 1 calc R . .
H21B H 0.4107 0.5497 0.3918 0.107 Uiso 1 1 calc R . .
C22 C 0.3639(4) 0.4835(6) 0.2748(3) 0.135(2) Uani 1 1 d . . .
H22A H 0.4025 0.5553 0.2542 0.203 Uiso 1 1 calc R . .
H22B H 0.2980 0.5208 0.2676 0.203 Uiso 1 1 calc R . .
H22C H 0.3616 0.3921 0.2444 0.203 Uiso 1 1 calc R . .
C23 C 0.5165(3) 0.2357(4) 0.3563(3) 0.0844(12) Uani 1 1 d . . .
H23A H 0.4637 0.2091 0.3079 0.101 Uiso 1 1 calc R . .
H23B H 0.5789 0.2173 0.3430 0.101 Uiso 1 1 calc R . .
C24 C 0.5102(3) 0.1414(5) 0.4263(3) 0.1155(17) Uani 1 1 d . . .
H24A H 0.4502 0.1630 0.4418 0.173 Uiso 1 1 calc R . .
H24B H 0.5659 0.1604 0.4729 0.173 Uiso 1 1 calc R . .
H24C H 0.5105 0.0388 0.4103 0.173 Uiso 1 1 calc R . .
N1B N 0.8372(6) 1.1197(10) 0.4822(6) 0.048(2) Uani 0.338(4) 1 d P B 2
N2B N 0.8603(5) 0.8757(8) 0.4957(6) 0.044(2) Uani 0.338(4) 1 d P B 2
N3B N 0.8584(5) 0.7392(8) 0.6140(4) 0.052(2) Uani 0.338(4) 1 d P B 2
H3D H 0.8905 0.6709 0.6509 0.062 Uiso 0.338(4) 1 d PR B 2
C1B C 0.8755(5) 1.0632(15) 0.4164(7) 0.040(3) Uani 0.338(4) 1 d PG B 2
C2B C 0.8983(9) 1.1369(8) 0.3502(10) 0.056(4) Uani 0.338(4) 1 d PG B 2
H2B H 0.8867 1.2385 0.3431 0.067 Uiso 0.338(4) 1 calc PR B 2
C3B C 0.9384(13) 1.0587(15) 0.2945(8) 0.078(7) Uani 0.338(4) 1 d PG B 2
H3B H 0.9536 1.1081 0.2502 0.093 Uiso 0.338(4) 1 calc PR B 2
C4B C 0.9557(11) 0.9068(15) 0.3051(8) 0.057(4) Uani 0.338(4) 1 d PG B 2
H4B H 0.9825 0.8545 0.2679 0.068 Uiso 0.338(4) 1 calc PR B 2
C5B C 0.9329(9) 0.8331(8) 0.3713(9) 0.055(4) Uani 0.338(4) 1 d PG B 2
H5B H 0.9445 0.7315 0.3784 0.066 Uiso 0.338(4) 1 calc PR B 2
C6B C 0.8928(7) 0.9113(16) 0.4270(5) 0.040(3) Uani 0.338(4) 1 d PG B 2
C7B C 0.8270(12) 1.007(3) 0.5231(11) 0.040(4) Uani 0.338(4) 1 d P B 2
C8B C 0.7956(7) 0.9923(16) 0.5980(5) 0.044(3) Uani 0.338(4) 1 d PG B 2
C9B C 0.7500(9) 1.1100(11) 0.6276(7) 0.064(4) Uani 0.338(4) 1 d PG B 2
H9B H 0.7415 1.2005 0.5996 0.077 Uiso 0.338(4) 1 calc PR B 2
C10B C 0.7170(12) 1.0923(15) 0.6991(8) 0.057(5) Uani 0.338(4) 1 d PG B 2
H10B H 0.6865 1.1710 0.7189 0.069 Uiso 0.338(4) 1 calc PR B 2
C11B C 0.7296(14) 0.9569(19) 0.7410(8) 0.092(8) Uani 0.338(4) 1 d PG B 2
H11B H 0.7076 0.9451 0.7888 0.111 Uiso 0.338(4) 1 calc PR B 2
C12B C 0.7753(10) 0.8392(12) 0.7114(8) 0.062(5) Uani 0.338(4) 1 d PG B 2
H12B H 0.7837 0.7486 0.7395 0.075 Uiso 0.338(4) 1 calc PR B 2
C13B C 0.8082(6) 0.8569(11) 0.6399(8) 0.046(3) Uani 0.338(4) 1 d PG B 2
C14B C 0.8592 0.7266 0.5255 0.040 Uani 0.34 1 d P B 2
H14B H 0.9177 0.6718 0.5199 0.048 Uiso 0.338(4) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.368(3) . ?
O1 H1 0.8704 . ?
N1A C7A 1.351(9) . ?
N1A C1A 1.377(6) . ?
N2A C6A 1.348(6) . ?
N2A C7A 1.350(11) . ?
N2A C14A 1.467(5) . ?
N3A C13A 1.399(5) . ?
N3A C14A 1.478(5) . ?
N3A H3C 0.9000 . ?
N4 C18 1.375(4) . ?
N4 C21 1.479(5) . ?
N4 C23 1.484(4) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9300 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9300 . ?
C7A C8A 1.423(8) . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9300 . ?
C14A C15 1.504(5) . ?
C14A H14A 0.9800 . ?
C15 C16 1.386(4) . ?
C15 C20 1.392(3) . ?
C15 C14B 1.512(3) . ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.407(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(4) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9300 . ?
C21 C22 1.426(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.459(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1B C7B 1.25(2) . ?
N1B C1B 1.429(13) . ?
N2B C6B 1.372(12) . ?
N2B C7B 1.39(2) . ?
N2B C14B 1.429(7) . ?
N3B C13B 1.398(10) . ?
N3B C14B 1.477(7) . ?
N3B H3D 0.8999 . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C2B C3B 1.3900 . ?
C2B H2B 0.9300 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9300 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9300 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9300 . ?
C7B C8B 1.429(17) . ?
C8B C9B 1.3900 . ?
C8B C13B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9300 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9300 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9300 . ?
C14B H14B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 H1 109.5 . . ?
C7A N1A C1A 104.5(6) . . ?
C6A N2A C7A 108.1(5) . . ?
C6A N2A C14A 127.6(5) . . ?
C7A N2A C14A 123.5(5) . . ?
C13A N3A C14A 121.2(4) . . ?
C13A N3A H3C 119.2 . . ?
C14A N3A H3C 119.6 . . ?
C18 N4 C21 122.4(3) . . ?
C18 N4 C23 120.9(3) . . ?
C21 N4 C23 116.4(3) . . ?
N1A C1A C2A 130.3(5) . . ?
N1A C1A C6A 109.6(5) . . ?
C2A C1A C6A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
N2A C6A C5A 133.6(5) . . ?
N2A C6A C1A 106.3(5) . . ?
C5A C6A C1A 120.0 . . ?
N2A C7A N1A 111.4(7) . . ?
N2A C7A C8A 120.4(7) . . ?
N1A C7A C8A 128.2(8) . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A C7A 121.9(7) . . ?
C13A C8A C7A 118.0(7) . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
C12A C13A N3A 121.8(6) . . ?
C8A C13A N3A 118.1(6) . . ?
N2A C14A N3A 105.5(3) . . ?
N2A C14A C15 113.8(3) . . ?
N3A C14A C15 113.6(3) . . ?
N2A C14A H14A 107.9 . . ?
N3A C14A H14A 107.9 . . ?
C15 C14A H14A 107.9 . . ?
C16 C15 C20 116.3(2) . . ?
C16 C15 C14A 124.9(2) . . ?
C20 C15 C14A 118.7(3) . . ?
C16 C15 C14B 125.4(2) . . ?
C20 C15 C14B 118.3(2) . . ?
C14A C15 C14B 0.53(16) . . ?
C17 C16 C15 123.2(3) . . ?
C17 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
N4 C18 C19 120.5(3) . . ?
N4 C18 C17 122.7(3) . . ?
C19 C18 C17 116.8(3) . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
O1 C20 C19 121.0(2) . . ?
O1 C20 C15 117.3(2) . . ?
C19 C20 C15 121.7(2) . . ?
C22 C21 N4 110.7(4) . . ?
C22 C21 H21A 109.5 . . ?
N4 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N4 112.8(4) . . ?
C24 C23 H23A 109.0 . . ?
N4 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
N4 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7B N1B C1B 104.1(12) . . ?
C6B N2B C7B 106.7(12) . . ?
C6B N2B C14B 122.8(9) . . ?
C7B N2B C14B 130.4(12) . . ?
C13B N3B C14B 119.9(7) . . ?
C13B N3B H3D 120.5 . . ?
C14B N3B H3D 119.6 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B N1B 130.0(12) . . ?
C6B C1B N1B 109.9(12) . . ?
C1B C2B C3B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
N2B C6B C5B 135.5(12) . . ?
N2B C6B C1B 104.5(12) . . ?
C5B C6B C1B 120.0 . . ?
N1B C7B N2B 114.6(15) . . ?
N1B C7B C8B 130.6(18) . . ?
N2B C7B C8B 114.5(18) . . ?
C9B C8B C13B 120.0 . . ?
C9B C8B C7B 120.8(14) . . ?
C13B C8B C7B 119.1(14) . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C12B C13B C8B 120.0 . . ?
C12B C13B N3B 118.8(11) . . ?
C8B C13B N3B 121.2(11) . . ?
N2B C14B N3B 106.0(5) . . ?
N2B C14B C15 111.2(3) . . ?
N3B C14B C15 107.0(3) . . ?
N2B C14B H14B 110.8 . . ?
N3B C14B H14B 110.8 . . ?
C15 C14B H14B 110.8 . . ?

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
C7A N1A C1A C2A 177.5(5) . . . . ?
C7A N1A C1A C6A 0.5(5) . . . . ?
N1A C1A C2A C3A -176.8(6) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C7A N2A C6A C5A -177.3(5) . . . . ?
C14A N2A C6A C5A 12.9(7) . . . . ?
C7A N2A C6A C1A -0.4(5) . . . . ?
C14A N2A C6A C1A -170.2(4) . . . . ?
C4A C5A C6A N2A 176.6(6) . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
N1A C1A C6A N2A -0.1(4) . . . . ?
C2A C1A C6A N2A -177.5(4) . . . . ?
N1A C1A C6A C5A 177.4(4) . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C6A N2A C7A N1A 0.7(7) . . . . ?
C14A N2A C7A N1A 171.0(5) . . . . ?
C6A N2A C7A C8A -178.9(6) . . . . ?
C14A N2A C7A C8A -8.6(10) . . . . ?
C1A N1A C7A N2A -0.7(7) . . . . ?
C1A N1A C7A C8A 178.8(7) . . . . ?
N2A C7A C8A C9A 174.1(5) . . . . ?
N1A C7A C8A C9A -5.4(11) . . . . ?
N2A C7A C8A C13A -10.3(9) . . . . ?
N1A C7A C8A C13A 170.2(6) . . . . ?
C13A C8A C9A C10A 0.0 . . . . ?
C7A C8A C9A C10A 175.4(6) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C8A 0.0 . . . . ?
C11A C12A C13A N3A -176.0(5) . . . . ?
C9A C8A C13A C12A 0.0 . . . . ?
C7A C8A C13A C12A -175.6(5) . . . . ?
C9A C8A C13A N3A 176.1(4) . . . . ?
C7A C8A C13A N3A 0.5(6) . . . . ?
C14A N3A C13A C12A -155.5(4) . . . . ?
C14A N3A C13A C8A 28.5(5) . . . . ?
C6A N2A C14A N3A -159.5(4) . . . . ?
C7A N2A C14A N3A 32.1(6) . . . . ?
C6A N2A C14A C15 75.2(5) . . . . ?
C7A N2A C14A C15 -93.1(6) . . . . ?
C13A N3A C14A N2A -42.2(5) . . . . ?
C13A N3A C14A C15 83.2(4) . . . . ?
N2A C14A C15 C16 16.2(5) . . . . ?
N3A C14A C15 C16 -104.6(4) . . . . ?
N2A C14A C15 C20 -161.5(3) . . . . ?
N3A C14A C15 C20 77.7(4) . . . . ?
N2A C14A C15 C14B -137(19) . . . . ?
N3A C14A C15 C14B 103(19) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C14A C15 C16 C17 -176.9(3) . . . . ?
C14B C15 C16 C17 -176.6(2) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C21 N4 C18 C19 160.5(3) . . . . ?
C23 N4 C18 C19 -13.5(5) . . . . ?
C21 N4 C18 C17 -20.3(6) . . . . ?
C23 N4 C18 C17 165.7(3) . . . . ?
C16 C17 C18 N4 178.4(3) . . . . ?
C16 C17 C18 C19 -2.3(5) . . . . ?
N4 C18 C19 C20 -178.1(3) . . . . ?
C17 C18 C19 C20 2.7(5) . . . . ?
C18 C19 C20 O1 178.1(3) . . . . ?
C18 C19 C20 C15 -1.3(5) . . . . ?
C16 C15 C20 O1 -180.0(2) . . . . ?
C14A C15 C20 O1 -2.1(4) . . . . ?
C14B C15 C20 O1 -2.3(4) . . . . ?
C16 C15 C20 C19 -0.5(4) . . . . ?
C14A C15 C20 C19 177.4(3) . . . . ?
C14B C15 C20 C19 177.1(2) . . . . ?
C18 N4 C21 C22 106.8(4) . . . . ?
C23 N4 C21 C22 -79.0(5) . . . . ?
C18 N4 C23 C24 91.0(4) . . . . ?
C21 N4 C23 C24 -83.3(4) . . . . ?
C7B N1B C1B C2B 177.7(11) . . . . ?
C7B N1B C1B C6B -4.3(11) . . . . ?
C6B C1B C2B C3B 0.0 . . . . ?
N1B C1B C2B C3B 177.8(9) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C7B N2B C6B C5B -179.2(10) . . . . ?
C14B N2B C6B C5B -2.2(13) . . . . ?
C7B N2B C6B C1B -0.9(10) . . . . ?
C14B N2B C6B C1B 176.2(6) . . . . ?
C4B C5B C6B N2B 178.1(12) . . . . ?
C4B C5B C6B C1B 0.0 . . . . ?
C2B C1B C6B N2B -178.7(9) . . . . ?
N1B C1B C6B N2B 3.1(8) . . . . ?
C2B C1B C6B C5B 0.0 . . . . ?
N1B C1B C6B C5B -178.2(7) . . . . ?
C1B N1B C7B N2B 3.9(16) . . . . ?
C1B N1B C7B C8B 177.0(15) . . . . ?
C6B N2B C7B N1B -2.1(16) . . . . ?
C14B N2B C7B N1B -178.8(9) . . . . ?
C6B N2B C7B C8B -176.3(11) . . . . ?
C14B N2B C7B C8B 6.9(19) . . . . ?
N1B C7B C8B C9B 14(2) . . . . ?
N2B C7B C8B C9B -172.6(9) . . . . ?
N1B C7B C8B C13B -167.8(14) . . . . ?
N2B C7B C8B C13B 5.3(17) . . . . ?
C13B C8B C9B C10B 0.0 . . . . ?
C7B C8B C9B C10B 177.9(13) . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C8B 0.0 . . . . ?
C11B C12B C13B N3B 176.7(8) . . . . ?
C9B C8B C13B C12B 0.0 . . . . ?
C7B C8B C13B C12B -177.9(13) . . . . ?
C9B C8B C13B N3B -176.7(9) . . . . ?
C7B C8B C13B N3B 5.4(12) . . . . ?
C14B N3B C13B C12B 155.5(7) . . . . ?
C14B N3B C13B C8B -27.8(9) . . . . ?
C6B N2B C14B N3B 158.2(7) . . . . ?
C7B N2B C14B N3B -25.5(12) . . . . ?
C6B N2B C14B C15 -85.8(7) . . . . ?
C7B N2B C14B C15 90.5(12) . . . . ?
C13B N3B C14B N2B 34.2(8) . . . . ?
C13B N3B C14B C15 -84.6(7) . . . . ?
C16 C15 C14B N2B -26.0(5) . . . . ?
C20 C15 C14B N2B 156.5(5) . . . . ?
C14A C15 C14B N2B 1(19) . . . . ?
C16 C15 C14B N3B 89.3(4) . . . . ?
C20 C15 C14B N3B -88.1(4) . . . . ?
C14A C15 C14B N3B 117(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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 1425681'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 Cl Cu N4 O2'
_chemical_formula_weight         514.50

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   8.089(3)
_cell_length_b                   20.908(8)
_cell_length_c                   13.943(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.474(8)
_cell_angle_gamma                90.00
_cell_volume                     2358.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2222
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      22.72

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8145
_exptl_absorpt_correction_T_max  0.8914
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16112
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0959
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.63
_reflns_number_total             5458
_reflns_number_gt                3237
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0892P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5458
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C 0.8284(5) 0.12858(19) 0.5898(3) 0.0395(10) Uani 1 1 d . . .
C6 C 0.9490(5) 0.07931(18) 0.4419(3) 0.0367(9) Uani 1 1 d . . .
C7 C 0.9601(5) 0.09779(19) 0.5433(3) 0.0370(9) Uani 1 1 d . . .
C9 C 1.1062(6) 0.0869(2) 0.5949(3) 0.0455(11) Uani 1 1 d . . .
H9 H 1.1951 0.0677 0.5644 0.055 Uiso 1 1 calc R . .
C11 C 1.0303(5) 0.0551(2) 0.2955(3) 0.0434(10) Uani 1 1 d . . .
C12 C 0.3604(5) 0.1916(2) 0.4519(3) 0.0438(10) Uani 1 1 d . . .
C14 C 0.4704(5) 0.2256(2) 0.5113(3) 0.0443(10) Uani 1 1 d . . .
C15 C 0.8579(5) 0.0553(2) 0.2988(3) 0.0385(9) Uani 1 1 d . . .
C17 C 0.6169(5) 0.1999(2) 0.5522(3) 0.0452(11) Uani 1 1 d . . .
H17 H 0.6739 0.2263 0.5948 0.054 Uiso 1 1 calc R . .
C18 C 0.2200(6) 0.2218(2) 0.4157(4) 0.0594(13) Uani 1 1 d . . .
H18 H 0.1480 0.1989 0.3763 0.071 Uiso 1 1 calc R . .
C19 C 1.1211(6) 0.1041(2) 0.6893(4) 0.0547(13) Uani 1 1 d . . .
H19 H 1.2194 0.0967 0.7225 0.066 Uiso 1 1 calc R . .
C21 C 0.1844(7) 0.2852(3) 0.4366(4) 0.0690(15) Uani 1 1 d . . .
C22 C 0.7657(6) 0.0425(2) 0.2160(3) 0.0507(12) Uani 1 1 d . . .
H22 H 0.6507 0.0424 0.2169 0.061 Uiso 1 1 calc R . .
C23 C 1.1159(7) 0.0421(3) 0.2130(4) 0.0658(15) Uani 1 1 d . . .
H23 H 1.2308 0.0416 0.2120 0.079 Uiso 1 1 calc R . .
C24 C 0.8455(7) 0.1436(2) 0.6857(3) 0.0552(12) Uani 1 1 d . . .
H24 H 0.7568 0.1618 0.7178 0.066 Uiso 1 1 calc R . .
C26 C 0.2952(8) 0.3196(3) 0.4959(4) 0.0798(18) Uani 1 1 d . . .
H26 H 0.2750 0.3623 0.5103 0.096 Uiso 1 1 calc R . .
C28 C 0.9895(7) 0.1323(3) 0.7347(4) 0.0618(14) Uani 1 1 d . . .
H28 H 0.9987 0.1438 0.7990 0.074 Uiso 1 1 calc R . .
C29 C 0.4318(8) 0.2899(3) 0.5318(4) 0.0696(16) Uani 1 1 d . . .
H29 H 0.5028 0.3130 0.5715 0.083 Uiso 1 1 calc R . .
C31 C 1.0229(8) 0.0298(3) 0.1316(4) 0.0760(17) Uani 1 1 d . . .
H31 H 1.0764 0.0211 0.0743 0.091 Uiso 1 1 calc R . .
C32 C 0.8507(7) 0.0300(3) 0.1333(4) 0.0623(14) Uani 1 1 d . . .
H32 H 0.7920 0.0216 0.0770 0.075 Uiso 1 1 calc R . .
C37 C -0.0630(12) 0.2733(5) 0.2887(8) 0.160(5) Uani 1 1 d . . .
H37A H -0.0488 0.3187 0.2816 0.240 Uiso 1 1 calc R . .
H37B H -0.1300 0.2573 0.2369 0.240 Uiso 1 1 calc R . .
H37C H 0.0431 0.2528 0.2878 0.240 Uiso 1 1 calc R . .
C38 C -0.1312(15) 0.2621(5) 0.3656(9) 0.203(7) Uani 1 1 d . . .
H38A H -0.1254 0.2182 0.3877 0.244 Uiso 1 1 calc R . .
H38B H -0.2398 0.2809 0.3736 0.244 Uiso 1 1 calc R . .
C3A C -0.0152(15) 0.3806(5) 0.4380(12) 0.192(7) Uani 1 1 d . . .
H3A1 H -0.1338 0.3852 0.4295 0.231 Uiso 1 1 calc R . .
H3A2 H 0.0134 0.3867 0.5051 0.231 Uiso 1 1 calc R . .
C5A C 0.065(2) 0.4188(7) 0.3838(11) 0.205(6) Uani 1 1 d . . .
H5A1 H 0.1812 0.4127 0.3935 0.307 Uiso 1 1 calc R . .
H5A2 H 0.0361 0.4622 0.3992 0.307 Uiso 1 1 calc R . .
H5A3 H 0.0367 0.4104 0.3180 0.307 Uiso 1 1 calc R . .
C11A C 0.362(3) 0.1620(13) 0.2022(13) 0.38(2) Uani 1 1 d . . .
H11A H 0.2743 0.1883 0.2255 0.569 Uiso 1 1 calc R . .
H11B H 0.3837 0.1280 0.2468 0.569 Uiso 1 1 calc R . .
H11C H 0.3316 0.1443 0.1411 0.569 Uiso 1 1 calc R . .
Cl1 Cl 0.46711(13) -0.00536(5) 0.37720(8) 0.0481(3) Uani 1 1 d . . .
Cu1 Cu 0.58665(6) 0.08199(2) 0.44604(4) 0.0411(2) Uani 1 1 d . . .
N2A N 0.8110(4) 0.07042(15) 0.3922(2) 0.0359(8) Uani 1 1 d . . .
N1A N 1.0842(4) 0.06958(17) 0.3876(3) 0.0440(9) Uani 1 1 d . . .
H2 H 1.1854 0.0719 0.4067 0.053 Uiso 1 1 calc R . .
N3A N 0.6816(4) 0.14356(16) 0.5373(2) 0.0370(8) Uani 1 1 d . . .
N4 N 0.0485(8) 0.3143(3) 0.3991(5) 0.114(2) Uani 1 1 d . . .
O1 O 0.3864(3) 0.13065(14) 0.4286(2) 0.0507(8) Uani 1 1 d . . .
O2 O 0.485(2) 0.1939(10) 0.193(2) 0.403(11) Uani 1 1 d . . .
H2A H 0.4596 0.2318 0.1910 0.604 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 C24 1.380(6) . ?
C5 C7 1.407(6) . ?
C5 N3A 1.424(5) . ?
C6 N2A 1.322(5) . ?
C6 N1A 1.351(5) . ?
C6 C7 1.468(6) . ?
C7 C9 1.397(6) . ?
C9 C19 1.369(7) . ?
C9 H9 0.9300 . ?
C11 C23 1.375(6) . ?
C11 N1A 1.386(6) . ?
C11 C15 1.396(6) . ?
C12 O1 1.332(5) . ?
C12 C18 1.391(6) . ?
C12 C14 1.404(6) . ?
C14 C29 1.409(7) . ?
C14 C17 1.417(6) . ?
C15 C22 1.395(6) . ?
C15 N2A 1.396(5) . ?
C17 N3A 1.306(5) . ?
C17 H17 0.9300 . ?
C18 C21 1.388(7) . ?
C18 H18 0.9300 . ?
C19 C28 1.376(7) . ?
C19 H19 0.9300 . ?
C21 N4 1.357(7) . ?
C21 C26 1.410(8) . ?
C22 C32 1.373(6) . ?
C22 H22 0.9300 . ?
C23 C31 1.381(7) . ?
C23 H23 0.9300 . ?
C24 C28 1.366(7) . ?
C24 H24 0.9300 . ?
C26 C29 1.359(7) . ?
C26 H26 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C31 C32 1.394(8) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C37 C38 1.232(11) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 N4 1.874(15) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C3A C5A 1.279(16) . ?
C3A N4 1.577(14) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C11A O2 1.20(2) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
Cl1 Cu1 2.2752(13) . ?
Cu1 O1 1.927(3) . ?
Cu1 N3A 1.962(3) . ?
Cu1 N2A 1.984(3) . ?
N1A H2 0.8600 . ?
O2 H2A 0.8200 . ?

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
C24 C5 C7 118.7(4) . . ?
C24 C5 N3A 121.6(4) . . ?
C7 C5 N3A 119.7(4) . . ?
N2A C6 N1A 111.7(4) . . ?
N2A C6 C7 125.9(4) . . ?
N1A C6 C7 122.4(4) . . ?
C9 C7 C5 118.6(4) . . ?
C9 C7 C6 119.8(4) . . ?
C5 C7 C6 121.6(4) . . ?
C19 C9 C7 121.3(4) . . ?
C19 C9 H9 119.3 . . ?
C7 C9 H9 119.3 . . ?
C23 C11 N1A 131.4(4) . . ?
C23 C11 C15 122.6(4) . . ?
N1A C11 C15 106.0(4) . . ?
O1 C12 C18 118.4(4) . . ?
O1 C12 C14 121.9(4) . . ?
C18 C12 C14 119.7(4) . . ?
C12 C14 C29 117.5(4) . . ?
C12 C14 C17 124.7(4) . . ?
C29 C14 C17 117.8(4) . . ?
C22 C15 N2A 131.9(4) . . ?
C22 C15 C11 120.0(4) . . ?
N2A C15 C11 108.1(4) . . ?
N3A C17 C14 127.8(4) . . ?
N3A C17 H17 116.1 . . ?
C14 C17 H17 116.1 . . ?
C21 C18 C12 121.9(5) . . ?
C21 C18 H18 119.1 . . ?
C12 C18 H18 119.1 . . ?
C9 C19 C28 119.5(5) . . ?
C9 C19 H19 120.3 . . ?
C28 C19 H19 120.3 . . ?
N4 C21 C18 121.0(5) . . ?
N4 C21 C26 120.4(5) . . ?
C18 C21 C26 118.5(5) . . ?
C32 C22 C15 117.6(4) . . ?
C32 C22 H22 121.2 . . ?
C15 C22 H22 121.2 . . ?
C11 C23 C31 116.7(5) . . ?
C11 C23 H23 121.6 . . ?
C31 C23 H23 121.6 . . ?
C28 C24 C5 121.6(5) . . ?
C28 C24 H24 119.2 . . ?
C5 C24 H24 119.2 . . ?
C29 C26 C21 119.6(5) . . ?
C29 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
C24 C28 C19 120.3(5) . . ?
C24 C28 H28 119.9 . . ?
C19 C28 H28 119.9 . . ?
C26 C29 C14 122.8(5) . . ?
C26 C29 H29 118.6 . . ?
C14 C29 H29 118.6 . . ?
C23 C31 C32 121.6(5) . . ?
C23 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C22 C32 C31 121.5(5) . . ?
C22 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C37 C38 N4 75.7(10) . . ?
C37 C38 H38A 115.9 . . ?
N4 C38 H38A 115.9 . . ?
C37 C38 H38B 115.9 . . ?
N4 C38 H38B 115.9 . . ?
H38A C38 H38B 112.9 . . ?
C5A C3A N4 100.3(15) . . ?
C5A C3A H3A1 111.7 . . ?
N4 C3A H3A1 111.7 . . ?
C5A C3A H3A2 111.7 . . ?
N4 C3A H3A2 111.7 . . ?
H3A1 C3A H3A2 109.5 . . ?
C3A C5A H5A1 109.5 . . ?
C3A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C3A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
O2 C11A H11A 109.5 . . ?
O2 C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
O2 C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O1 Cu1 N3A 93.44(14) . . ?
O1 Cu1 N2A 141.91(14) . . ?
N3A Cu1 N2A 88.33(13) . . ?
O1 Cu1 Cl1 90.94(10) . . ?
N3A Cu1 Cl1 164.35(11) . . ?
N2A Cu1 Cl1 97.43(10) . . ?
C6 N2A C15 106.6(3) . . ?
C6 N2A Cu1 123.7(3) . . ?
C15 N2A Cu1 129.6(3) . . ?
C6 N1A C11 107.6(4) . . ?
C6 N1A H2 126.2 . . ?
C11 N1A H2 126.2 . . ?
C17 N3A C5 116.7(3) . . ?
C17 N3A Cu1 122.7(3) . . ?
C5 N3A Cu1 120.6(3) . . ?
C21 N4 C3A 121.8(7) . . ?
C21 N4 C38 117.4(5) . . ?
C3A N4 C38 110.0(6) . . ?
C12 O1 Cu1 127.5(3) . . ?
C11A O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 C5 C7 C9 -3.6(6) . . . . ?
N3A C5 C7 C9 176.4(4) . . . . ?
C24 C5 C7 C6 178.8(4) . . . . ?
N3A C5 C7 C6 -1.3(6) . . . . ?
N2A C6 C7 C9 160.5(4) . . . . ?
N1A C6 C7 C9 -19.9(6) . . . . ?
N2A C6 C7 C5 -21.9(6) . . . . ?
N1A C6 C7 C5 157.8(4) . . . . ?
C5 C7 C9 C19 1.7(6) . . . . ?
C6 C7 C9 C19 179.4(4) . . . . ?
O1 C12 C14 C29 180.0(4) . . . . ?
C18 C12 C14 C29 0.1(7) . . . . ?
O1 C12 C14 C17 -0.1(7) . . . . ?
C18 C12 C14 C17 -180.0(5) . . . . ?
C23 C11 C15 C22 -0.6(7) . . . . ?
N1A C11 C15 C22 179.8(4) . . . . ?
C23 C11 C15 N2A -179.8(4) . . . . ?
N1A C11 C15 N2A 0.6(5) . . . . ?
C12 C14 C17 N3A 5.5(7) . . . . ?
C29 C14 C17 N3A -174.6(5) . . . . ?
O1 C12 C18 C21 -179.9(5) . . . . ?
C14 C12 C18 C21 -0.1(8) . . . . ?
C7 C9 C19 C28 0.3(7) . . . . ?
C12 C18 C21 N4 178.7(6) . . . . ?
C12 C18 C21 C26 0.4(9) . . . . ?
N2A C15 C22 C32 178.9(5) . . . . ?
C11 C15 C22 C32 0.0(7) . . . . ?
N1A C11 C23 C31 -179.6(5) . . . . ?
C15 C11 C23 C31 0.8(8) . . . . ?
C7 C5 C24 C28 3.5(7) . . . . ?
N3A C5 C24 C28 -176.4(5) . . . . ?
N4 C21 C26 C29 -179.1(7) . . . . ?
C18 C21 C26 C29 -0.9(10) . . . . ?
C5 C24 C28 C19 -1.5(8) . . . . ?
C9 C19 C28 C24 -0.4(8) . . . . ?
C21 C26 C29 C14 1.0(10) . . . . ?
C12 C14 C29 C26 -0.6(8) . . . . ?
C17 C14 C29 C26 179.5(6) . . . . ?
C11 C23 C31 C32 -0.5(9) . . . . ?
C15 C22 C32 C31 0.4(8) . . . . ?
C23 C31 C32 C22 -0.1(9) . . . . ?
N1A C6 N2A C15 -1.4(5) . . . . ?
C7 C6 N2A C15 178.3(4) . . . . ?
N1A C6 N2A Cu1 -178.7(3) . . . . ?
C7 C6 N2A Cu1 1.0(6) . . . . ?
C22 C15 N2A C6 -178.6(5) . . . . ?
C11 C15 N2A C6 0.5(5) . . . . ?
C22 C15 N2A Cu1 -1.5(7) . . . . ?
C11 C15 N2A Cu1 177.5(3) . . . . ?
O1 Cu1 N2A C6 120.5(3) . . . . ?
N3A Cu1 N2A C6 27.1(3) . . . . ?
Cl1 Cu1 N2A C6 -138.4(3) . . . . ?
O1 Cu1 N2A C15 -56.1(4) . . . . ?
N3A Cu1 N2A C15 -149.6(4) . . . . ?
Cl1 Cu1 N2A C15 45.0(3) . . . . ?
N2A C6 N1A C11 1.8(5) . . . . ?
C7 C6 N1A C11 -177.9(4) . . . . ?
C23 C11 N1A C6 179.0(5) . . . . ?
C15 C11 N1A C6 -1.4(5) . . . . ?
C14 C17 N3A C5 -178.3(4) . . . . ?
C14 C17 N3A Cu1 2.7(6) . . . . ?
C24 C5 N3A C17 42.8(6) . . . . ?
C7 C5 N3A C17 -137.2(4) . . . . ?
C24 C5 N3A Cu1 -138.2(4) . . . . ?
C7 C5 N3A Cu1 41.9(5) . . . . ?
O1 Cu1 N3A C17 -10.7(4) . . . . ?
N2A Cu1 N3A C17 131.2(3) . . . . ?
Cl1 Cu1 N3A C17 -116.7(4) . . . . ?
O1 Cu1 N3A C5 170.4(3) . . . . ?
N2A Cu1 N3A C5 -47.7(3) . . . . ?
Cl1 Cu1 N3A C5 64.4(5) . . . . ?
C18 C21 N4 C3A 166.9(8) . . . . ?
C26 C21 N4 C3A -14.8(12) . . . . ?
C18 C21 N4 C38 26.1(10) . . . . ?
C26 C21 N4 C38 -155.7(7) . . . . ?
C5A C3A N4 C21 90.1(13) . . . . ?
C5A C3A N4 C38 -126.5(11) . . . . ?
C37 C38 N4 C21 -101.1(8) . . . . ?
C37 C38 N4 C3A 113.7(9) . . . . ?
C18 C12 O1 Cu1 166.8(3) . . . . ?
C14 C12 O1 Cu1 -13.1(6) . . . . ?
N3A Cu1 O1 C12 16.2(4) . . . . ?
N2A Cu1 O1 C12 -75.4(4) . . . . ?
Cl1 Cu1 O1 C12 -178.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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 1425682'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N3.20 O2.80 Zn0.80'
_chemical_formula_weight         430.34

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   20.646(2)
_cell_length_b                   18.537(2)
_cell_length_c                   15.4375(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.913(2)
_cell_angle_gamma                90.00
_cell_volume                     5220.7(10)
_cell_formula_units_Z            10
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2254
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.02

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2248
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_T_max  0.9000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14747
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.42
_reflns_number_total             7163
_reflns_number_gt                4439
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.1119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         7163
_refine_ls_number_parameters     658
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3836(9) 0.0666(9) 0.9290(12) 0.075(6) Uani 1 1 d . . .
H32A H 0.4082 0.1028 0.9781 0.113 Uiso 1 1 calc R . .
H32B H 0.3623 0.0314 0.9538 0.113 Uiso 1 1 calc R . .
H32C H 0.3457 0.0888 0.8713 0.113 Uiso 1 1 calc R . .
C2 C 0.4367(11) 0.0311(11) 0.9044(14) 0.089(6) Uani 1 1 d . . .
H31A H 0.4118 -0.0070 0.8574 0.106 Uiso 1 1 calc R . .
H31B H 0.4746 0.0089 0.9631 0.106 Uiso 1 1 calc R . .
C3 C 0.5343(13) 0.1953(12) 0.9609(14) 0.125(8) Uani 1 1 d . . .
H34A H 0.5051 0.2238 0.9038 0.188 Uiso 1 1 calc R . .
H34B H 0.5815 0.2176 0.9976 0.188 Uiso 1 1 calc R . .
H34C H 0.5103 0.1922 1.0011 0.188 Uiso 1 1 calc R . .
C4 C 0.5438(9) 0.1221(9) 0.9305(13) 0.063(5) Uani 1 1 d . . .
H33A H 0.5710 0.0934 0.9891 0.076 Uiso 1 1 calc R . .
H33B H 0.5735 0.1258 0.8973 0.076 Uiso 1 1 calc R . .
C5 C 0.4371(9) 0.1064(10) 0.7649(12) 0.051(5) Uani 1 1 d . . .
C6 C 0.3726(10) 0.0694(9) 0.6990(14) 0.048(5) Uani 1 1 d . . .
H29 H 0.3555 0.0335 0.7251 0.058 Uiso 1 1 calc R . .
C7 C 0.3361(5) 0.0811(7) 0.6071(10) 0.029(3) Uani 1 1 d . . .
C8 C 0.3667(9) 0.1313(9) 0.5581(12) 0.038(4) Uani 1 1 d . . .
C9 C 0.4301(10) 0.1710(10) 0.6310(13) 0.059(5) Uani 1 1 d . . .
H26 H 0.4479 0.2081 0.6077 0.071 Uiso 1 1 calc R . .
C10 C 0.4658(10) 0.1590(9) 0.7301(12) 0.057(5) Uani 1 1 d . . .
H27 H 0.5073 0.1851 0.7717 0.069 Uiso 1 1 calc R . .
C11 C 0.3410(6) 0.1481(6) 0.4611(9) 0.032(3) Uani 1 1 d . . .
H24 H 0.3679 0.1820 0.4468 0.038 Uiso 1 1 calc R . .
C12 C 0.2678(9) 0.1407(8) 0.2894(10) 0.036(4) Uani 1 1 d . . .
C13 C 0.2859(9) 0.2095(8) 0.2684(11) 0.049(4) Uani 1 1 d . . .
H21 H 0.3104 0.2436 0.3171 0.059 Uiso 1 1 calc R . .
C14 C 0.2654(10) 0.2226(8) 0.1736(14) 0.059(5) Uani 1 1 d . . .
H20 H 0.2723 0.2694 0.1578 0.071 Uiso 1 1 calc R . .
C15 C 0.2354(9) 0.1746(9) 0.0979(11) 0.050(4) Uani 1 1 d . . .
H19 H 0.2282 0.1847 0.0350 0.060 Uiso 1 1 calc R . .
C16 C 0.2170(8) 0.1102(7) 0.1236(10) 0.043(4) Uani 1 1 d . . .
H18 H 0.1943 0.0767 0.0736 0.051 Uiso 1 1 calc R . .
C17 C 0.2280(9) 0.0899(9) 0.2133(11) 0.046(4) Uani 1 1 d . . .
C18 C 0.2102(8) 0.0191(8) 0.2274(9) 0.029(3) Uani 1 1 d . . .
C19 C 0.1827(9) -0.0955(8) 0.1950(10) 0.038(4) Uani 1 1 d . . .
C20 C 0.1725(11) -0.1702(8) 0.1656(13) 0.058(5) Uani 1 1 d . . .
H44 H 0.1811 -0.1878 0.1155 0.070 Uiso 1 1 calc R . .
C21 C 0.1491(11) -0.2128(9) 0.2177(14) 0.070(6) Uani 1 1 d . . .
H45 H 0.1366 -0.2599 0.1956 0.085 Uiso 1 1 calc R . .
C22 C 0.1418(9) -0.1945(9) 0.2975(12) 0.065(5) Uani 1 1 d . . .
H46 H 0.1272 -0.2287 0.3290 0.078 Uiso 1 1 calc R . .
C23 C 0.1565(8) -0.1237(9) 0.3320(12) 0.040(4) Uani 1 1 d . . .
H47 H 0.1534 -0.1101 0.3879 0.048 Uiso 1 1 calc R . .
C24 C 0.1755(6) -0.0752(8) 0.2822(10) 0.029(4) Uani 1 1 d . . .
C25 C 0.0836(7) 0.0757(10) 0.4023(11) 0.050(4) Uani 1 1 d . . .
C26 C 0.0126(11) 0.0897(11) 0.3953(19) 0.111(8) Uani 1 1 d . . .
H2A1 H -0.0218 0.0545 0.3532 0.166 Uiso 1 1 calc R . .
H2A2 H -0.0035 0.1371 0.3688 0.166 Uiso 1 1 calc R . .
H2A3 H 0.0159 0.0869 0.4593 0.166 Uiso 1 1 calc R . .
C27 C 0.5405(9) 0.3216(8) 0.6548(11) 0.077(4) Uani 1 1 d . . .
H4A2 H 0.4987 0.2938 0.6463 0.116 Uiso 1 1 calc R . .
H4A3 H 0.5552 0.3529 0.7104 0.116 Uiso 1 1 calc R . .
H4A4 H 0.5801 0.2897 0.6653 0.116 Uiso 1 1 calc R . .
C28 C 0.481(3) 0.4397(10) 0.591(5) 0.37(3) Uani 1 1 d . . .
H8A1 H 0.4438 0.4664 0.5368 0.557 Uiso 1 1 calc R . .
H8A2 H 0.5187 0.4719 0.6331 0.557 Uiso 1 1 calc R . .
H8A3 H 0.4589 0.4170 0.6267 0.557 Uiso 1 1 calc R . .
C29 C 0.5171(17) 0.375(2) 0.547(5) 0.34(4) Uani 1 1 d . . .
H6A H 0.5503 0.3848 0.5190 0.414 Uiso 1 1 calc R . .
C30 C 0.2446(7) 0.4092(7) 0.4211(9) 0.024(3) Uani 1 1 d . . .
C31 C 0.2655(10) 0.3899(9) 0.5224(11) 0.058(5) Uani 1 1 d . . .
H14 H 0.2895 0.4215 0.5746 0.070 Uiso 1 1 calc R . .
C32 C 0.2464(12) 0.3201(9) 0.5339(13) 0.073(6) Uani 1 1 d . . .
H15 H 0.2620 0.3044 0.5978 0.087 Uiso 1 1 calc R . .
C33 C 0.2063(9) 0.2711(8) 0.4596(10) 0.046(4) Uani 1 1 d . . .
H16 H 0.1897 0.2273 0.4708 0.056 Uiso 1 1 calc R . .
C34 C 0.1932(9) 0.2942(7) 0.3654(10) 0.040(4) Uani 1 1 d . . .
H17 H 0.1700 0.2616 0.3141 0.048 Uiso 1 1 calc R . .
C35 C 0.2111(8) 0.3586(8) 0.3431(11) 0.034(4) Uani 1 1 d . . .
C36 C 0.2668(8) 0.4843(8) 0.4062(12) 0.037(4) Uani 1 1 d . . .
C37 C 0.2943(8) 0.6019(8) 0.4318(11) 0.039(4) Uani 1 1 d . . .
C38 C 0.3097(10) 0.6661(9) 0.4706(14) 0.057(5) Uani 1 1 d . . .
H41 H 0.3106 0.6755 0.5303 0.068 Uiso 1 1 calc R . .
C39 C 0.3248(10) 0.7200(8) 0.4204(14) 0.055(5) Uani 1 1 d . . .
H40 H 0.3295 0.7682 0.4393 0.066 Uiso 1 1 calc R . .
C40 C 0.3325(9) 0.6965(7) 0.3375(11) 0.051(5) Uani 1 1 d . . .
H39 H 0.3453 0.7311 0.3045 0.062 Uiso 1 1 calc R . .
C41 C 0.3230(9) 0.6294(10) 0.3037(12) 0.047(4) Uani 1 1 d . . .
H38 H 0.3298 0.6166 0.2503 0.057 Uiso 1 1 calc R . .
C42 C 0.3011(8) 0.5770(8) 0.3559(11) 0.042(4) Uani 1 1 d . . .
C43 C 0.3870(11) 0.4246(12) 0.2286(17) 0.095(8) Uani 1 1 d . . .
C44 C 0.4658(8) 0.3993(12) 0.2388(19) 0.123(10) Uani 1 1 d . . .
H1A1 H 0.4940 0.3765 0.3012 0.185 Uiso 1 1 calc R . .
H1A2 H 0.4917 0.4406 0.2337 0.185 Uiso 1 1 calc R . .
H1A3 H 0.4580 0.3657 0.1874 0.185 Uiso 1 1 calc R . .
C45 C 0.1401(8) 0.3555(8) 0.1760(11) 0.057(5) Uani 1 1 d . . .
H11 H 0.1102 0.3268 0.1918 0.069 Uiso 1 1 calc R . .
C46 C 0.1144(9) 0.3677(9) 0.0694(12) 0.040(4) Uani 1 1 d . . .
C47 C 0.0479(10) 0.3363(9) 0.0079(13) 0.056(5) Uani 1 1 d . . .
H7 H 0.0248 0.3073 0.0342 0.067 Uiso 1 1 calc R . .
C48 C 0.0164(10) 0.3471(10) -0.0886(14) 0.059(5) Uani 1 1 d . . .
H6 H -0.0240 0.3192 -0.1287 0.071 Uiso 1 1 calc R . .
C49 C 0.0422(9) 0.4006(9) -0.1344(11) 0.042(4) Uani 1 1 d . . .
C50 C 0.1089(8) 0.4322(9) -0.0696(10) 0.040(4) Uani 1 1 d . . .
H10 H 0.1312 0.4637 -0.0945 0.048 Uiso 1 1 calc R . .
C51 C 0.0328(9) 0.4679(7) -0.2750(11) 0.045(4) Uani 1 1 d . . .
H4A H 0.0509 0.5085 -0.2302 0.054 Uiso 1 1 calc R . .
H4B H -0.0069 0.4843 -0.3367 0.054 Uiso 1 1 calc R . .
C52 C 0.0944(11) 0.4347(9) -0.2907(14) 0.097(7) Uani 1 1 d . . .
H3A H 0.1351 0.4231 -0.2284 0.146 Uiso 1 1 calc R . .
H3B H 0.1098 0.4686 -0.3245 0.146 Uiso 1 1 calc R . .
H3C H 0.0769 0.3916 -0.3293 0.146 Uiso 1 1 calc R . .
C53 C -0.0615(9) 0.3795(12) -0.2968(13) 0.082(7) Uani 1 1 d . . .
H2A H -0.0870 0.4117 -0.3520 0.098 Uiso 1 1 calc R . .
H2B H -0.0910 0.3740 -0.2633 0.098 Uiso 1 1 calc R . .
C54 C -0.0507(8) 0.3099(9) -0.3308(13) 0.070(5) Uani 1 1 d . . .
H1A H -0.0132 0.3138 -0.3506 0.105 Uiso 1 1 calc R . .
H1B H -0.0956 0.2945 -0.3855 0.105 Uiso 1 1 calc R . .
H1C H -0.0361 0.2753 -0.2787 0.105 Uiso 1 1 calc R . .
C55 C 0.1461(9) 0.4175(8) 0.0387(10) 0.051(4) Uani 1 1 d . . .
N4 N 0.4724(6) 0.0808(7) 0.8624(9) 0.040(3) Uani 1 1 d . . .
N1A N 0.2042(7) -0.0360(6) 0.1681(9) 0.040(3) Uani 1 1 d . . .
H8 H 0.2130 -0.0332 0.1190 0.048 Uiso 1 1 calc R . .
N2A N 0.1944(6) -0.0069(6) 0.2954(8) 0.029(3) Uani 1 1 d . . .
N3A N 0.2819(7) 0.1215(7) 0.3848(9) 0.036(3) Uani 1 1 d . . .
N5 N 0.0075(8) 0.4084(9) -0.2321(11) 0.083(5) Uani 1 1 d . . .
N2B N 0.2841(7) 0.5011(6) 0.3332(8) 0.037(3) Uani 1 1 d . . .
N1B N 0.2753(7) 0.5384(6) 0.4691(8) 0.040(3) Uani 1 1 d . . .
H5 H 0.2704 0.5356 0.5213 0.048 Uiso 1 1 calc R . .
N3B N 0.1971(7) 0.3793(7) 0.2467(9) 0.032(3) Uani 1 1 d . . .
O3 O 0.1208(7) 0.1215(7) 0.3853(11) 0.080(4) Uani 1 1 d . . .
O2 O 0.1107(6) 0.0180(7) 0.4317(8) 0.060(3) Uani 1 1 d . . .
O1 O 0.2722(5) 0.0484(6) 0.5496(8) 0.045(3) Uani 1 1 d . . .
O4 O 0.2069(6) 0.4544(5) 0.0892(8) 0.041(3) Uani 1 1 d . . .
O5 O 0.3645(6) 0.4878(8) 0.2045(9) 0.069(4) Uani 1 1 d . . .
O6 O 0.3598(5) 0.3763(6) 0.2611(10) 0.074(4) Uani 1 1 d . . .
O7 O 0.4544(18) 0.3515(14) 0.4999(19) 0.289(17) Uani 1 1 d . . .
H4A1 H 0.4266 0.3751 0.5132 0.434 Uiso 1 1 calc R . .
Zn1 Zn 0.27065(5) 0.43959(9) 0.22606(6) 0.0344(4) Uani 1 1 d . . .
Zn2 Zn 0.20808(5) 0.06067(9) 0.40905(6) 0.0360(4) 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 C2 1.47(3) . ?
C1 H32A 0.9600 . ?
C1 H32B 0.9600 . ?
C1 H32C 0.9600 . ?
C2 N4 1.50(2) . ?
C2 H31A 0.9700 . ?
C2 H31B 0.9700 . ?
C3 C4 1.48(2) . ?
C3 H34A 0.9600 . ?
C3 H34B 0.9600 . ?
C3 H34C 0.9600 . ?
C4 N4 1.55(2) . ?
C4 H33A 0.9700 . ?
C4 H33B 0.9700 . ?
C5 C10 1.37(2) . ?
C5 N4 1.413(19) . ?
C5 C6 1.42(2) . ?
C6 C7 1.28(2) . ?
C6 H29 0.9300 . ?
C7 O1 1.341(14) . ?
C7 C8 1.511(17) . ?
C8 C11 1.371(19) . ?
C8 C9 1.46(2) . ?
C9 C10 1.37(2) . ?
C9 H26 0.9300 . ?
C10 H27 0.9300 . ?
C11 N3A 1.331(16) . ?
C11 H24 0.9300 . ?
C12 N3A 1.407(17) . ?
C12 C13 1.41(2) . ?
C12 C17 1.43(2) . ?
C13 C14 1.34(2) . ?
C13 H21 0.9300 . ?
C14 C15 1.36(2) . ?
C14 H20 0.9300 . ?
C15 C16 1.37(2) . ?
C15 H19 0.9300 . ?
C16 C17 1.35(2) . ?
C16 H18 0.9300 . ?
C17 C18 1.41(2) . ?
C18 N2A 1.327(16) . ?
C18 N1A 1.339(17) . ?
C19 N1A 1.324(18) . ?
C19 C20 1.441(19) . ?
C19 C24 1.471(18) . ?
C20 C21 1.37(2) . ?
C20 H44 0.9300 . ?
C21 C22 1.35(2) . ?
C21 H45 0.9300 . ?
C22 C23 1.40(2) . ?
C22 H46 0.9300 . ?
C23 C24 1.354(19) . ?
C23 H47 0.9300 . ?
C24 N2A 1.312(16) . ?
C25 O2 1.195(18) . ?
C25 O3 1.25(2) . ?
C25 C26 1.44(2) . ?
C26 H2A1 0.9600 . ?
C26 H2A2 0.9600 . ?
C26 H2A3 0.9600 . ?
C27 C29 1.80(6) . ?
C27 H4A2 0.9600 . ?
C27 H4A3 0.9600 . ?
C27 H4A4 0.9600 . ?
C28 C29 1.72(7) . ?
C28 H8A1 0.9600 . ?
C28 H8A2 0.9600 . ?
C28 H8A3 0.9600 . ?
C29 O7 1.23(3) . ?
C29 H6A 0.9800 . ?
C30 C35 1.424(19) . ?
C30 C31 1.458(18) . ?
C30 C36 1.52(2) . ?
C31 C32 1.39(2) . ?
C31 H14 0.9300 . ?
C32 C33 1.39(2) . ?
C32 H15 0.9300 . ?
C33 C34 1.415(19) . ?
C33 H16 0.9300 . ?
C34 C35 1.343(19) . ?
C34 H17 0.9300 . ?
C35 N3B 1.428(17) . ?
C36 N1B 1.349(17) . ?
C36 N2B 1.367(18) . ?
C37 C38 1.30(2) . ?
C37 C42 1.33(2) . ?
C37 N1B 1.443(19) . ?
C38 C39 1.39(2) . ?
C38 H41 0.9300 . ?
C39 C40 1.43(2) . ?
C39 H40 0.9300 . ?
C40 C41 1.33(2) . ?
C40 H39 0.9300 . ?
C41 C42 1.46(2) . ?
C41 H38 0.9300 . ?
C42 N2B 1.453(16) . ?
C43 O5 1.25(2) . ?
C43 O6 1.28(2) . ?
C43 C44 1.63(3) . ?
C44 H1A1 0.9600 . ?
C44 H1A2 0.9600 . ?
C44 H1A3 0.9600 . ?
C45 N3B 1.252(19) . ?
C45 C46 1.49(2) . ?
C45 H11 0.9300 . ?
C46 C55 1.34(2) . ?
C46 C47 1.38(2) . ?
C47 C48 1.33(2) . ?
C47 H7 0.9300 . ?
C48 C49 1.46(2) . ?
C48 H6 0.9300 . ?
C49 N5 1.34(2) . ?
C49 C50 1.40(2) . ?
C50 C55 1.502(19) . ?
C50 H10 0.9300 . ?
C51 N5 1.501(19) . ?
C51 C52 1.53(2) . ?
C51 H4A 0.9700 . ?
C51 H4B 0.9700 . ?
C52 H3A 0.9600 . ?
C52 H3B 0.9600 . ?
C52 H3C 0.9600 . ?
C53 N5 1.41(2) . ?
C53 C54 1.45(2) . ?
C53 H2A 0.9700 . ?
C53 H2B 0.9700 . ?
C54 H1A 0.9600 . ?
C54 H1B 0.9600 . ?
C54 H1C 0.9600 . ?
C55 O4 1.317(19) . ?
N1A H8 0.8600 . ?
N2A Zn2 2.065(10) . ?
N3A Zn2 2.065(12) . ?
N2B Zn1 1.920(12) . ?
N1B H5 0.8600 . ?
N3B Zn1 2.028(12) . ?
O3 Zn2 2.009(12) . ?
O2 Zn2 2.336(10) . ?
O1 Zn2 1.956(11) . ?
O4 Zn1 1.915(11) . ?
O5 Zn1 2.295(12) . ?
O6 Zn1 2.031(11) . ?
O7 H4A1 0.8200 . ?

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
C2 C1 H32A 109.5 . . ?
C2 C1 H32B 109.5 . . ?
H32A C1 H32B 109.5 . . ?
C2 C1 H32C 109.5 . . ?
H32A C1 H32C 109.5 . . ?
H32B C1 H32C 109.5 . . ?
C1 C2 N4 114.3(15) . . ?
C1 C2 H31A 108.7 . . ?
N4 C2 H31A 108.7 . . ?
C1 C2 H31B 108.7 . . ?
N4 C2 H31B 108.7 . . ?
H31A C2 H31B 107.6 . . ?
C4 C3 H34A 109.5 . . ?
C4 C3 H34B 109.5 . . ?
H34A C3 H34B 109.5 . . ?
C4 C3 H34C 109.5 . . ?
H34A C3 H34C 109.5 . . ?
H34B C3 H34C 109.5 . . ?
C3 C4 N4 116.3(15) . . ?
C3 C4 H33A 108.2 . . ?
N4 C4 H33A 108.2 . . ?
C3 C4 H33B 108.2 . . ?
N4 C4 H33B 108.2 . . ?
H33A C4 H33B 107.4 . . ?
C10 C5 N4 123.6(14) . . ?
C10 C5 C6 119.7(15) . . ?
N4 C5 C6 116.3(15) . . ?
C7 C6 C5 125.7(16) . . ?
C7 C6 H29 117.2 . . ?
C5 C6 H29 117.2 . . ?
C6 C7 O1 123.0(12) . . ?
C6 C7 C8 119.5(11) . . ?
O1 C7 C8 117.4(12) . . ?
C11 C8 C9 118.4(13) . . ?
C11 C8 C7 130.4(12) . . ?
C9 C8 C7 111.0(13) . . ?
C10 C9 C8 126.7(16) . . ?
C10 C9 H26 116.6 . . ?
C8 C9 H26 116.6 . . ?
C9 C10 C5 116.4(15) . . ?
C9 C10 H27 121.8 . . ?
C5 C10 H27 121.8 . . ?
N3A C11 C8 127.4(11) . . ?
N3A C11 H24 116.3 . . ?
C8 C11 H24 116.3 . . ?
N3A C12 C13 121.6(13) . . ?
N3A C12 C17 116.9(13) . . ?
C13 C12 C17 121.3(13) . . ?
C14 C13 C12 115.7(14) . . ?
C14 C13 H21 122.1 . . ?
C12 C13 H21 122.1 . . ?
C13 C14 C15 126.9(16) . . ?
C13 C14 H20 116.6 . . ?
C15 C14 H20 116.6 . . ?
C14 C15 C16 113.4(14) . . ?
C14 C15 H19 123.3 . . ?
C16 C15 H19 123.3 . . ?
C17 C16 C15 127.3(13) . . ?
C17 C16 H18 116.3 . . ?
C15 C16 H18 116.3 . . ?
C16 C17 C18 119.3(14) . . ?
C16 C17 C12 114.6(14) . . ?
C18 C17 C12 125.4(13) . . ?
N2A C18 N1A 106.5(12) . . ?
N2A C18 C17 129.9(12) . . ?
N1A C18 C17 123.6(11) . . ?
N1A C19 C20 136.2(15) . . ?
N1A C19 C24 105.4(12) . . ?
C20 C19 C24 118.1(14) . . ?
C21 C20 C19 114.2(15) . . ?
C21 C20 H44 122.9 . . ?
C19 C20 H44 122.9 . . ?
C22 C21 C20 127.8(15) . . ?
C22 C21 H45 116.1 . . ?
C20 C21 H45 116.1 . . ?
C21 C22 C23 119.0(15) . . ?
C21 C22 H46 120.5 . . ?
C23 C22 H46 120.5 . . ?
C24 C23 C22 118.5(15) . . ?
C24 C23 H47 120.7 . . ?
C22 C23 H47 120.7 . . ?
N2A C24 C23 134.1(14) . . ?
N2A C24 C19 103.8(12) . . ?
C23 C24 C19 122.0(14) . . ?
O2 C25 O3 117.6(13) . . ?
O2 C25 C26 117.9(19) . . ?
O3 C25 C26 124.3(17) . . ?
C25 C26 H2A1 109.5 . . ?
C25 C26 H2A2 109.5 . . ?
H2A1 C26 H2A2 109.5 . . ?
C25 C26 H2A3 109.5 . . ?
H2A1 C26 H2A3 109.5 . . ?
H2A2 C26 H2A3 109.5 . . ?
C29 C27 H4A2 109.5 . . ?
C29 C27 H4A3 109.5 . . ?
H4A2 C27 H4A3 109.5 . . ?
C29 C27 H4A4 109.5 . . ?
H4A2 C27 H4A4 109.5 . . ?
H4A3 C27 H4A4 109.5 . . ?
C29 C28 H8A1 109.5 . . ?
C29 C28 H8A2 109.5 . . ?
H8A1 C28 H8A2 109.5 . . ?
C29 C28 H8A3 109.5 . . ?
H8A1 C28 H8A3 109.5 . . ?
H8A2 C28 H8A3 109.5 . . ?
O7 C29 C28 87(4) . . ?
O7 C29 C27 96(3) . . ?
C28 C29 C27 90(4) . . ?
O7 C29 H6A 124.6 . . ?
C28 C29 H6A 124.6 . . ?
C27 C29 H6A 124.6 . . ?
C35 C30 C31 121.9(12) . . ?
C35 C30 C36 122.4(12) . . ?
C31 C30 C36 115.5(12) . . ?
C32 C31 C30 114.0(14) . . ?
C32 C31 H14 123.0 . . ?
C30 C31 H14 123.0 . . ?
C31 C32 C33 126.7(14) . . ?
C31 C32 H15 116.7 . . ?
C33 C32 H15 116.7 . . ?
C32 C33 C34 113.9(13) . . ?
C32 C33 H16 123.1 . . ?
C34 C33 H16 123.1 . . ?
C35 C34 C33 126.1(13) . . ?
C35 C34 H17 117.0 . . ?
C33 C34 H17 117.0 . . ?
C34 C35 C30 116.8(12) . . ?
C34 C35 N3B 124.0(14) . . ?
C30 C35 N3B 119.1(13) . . ?
N1B C36 N2B 115.3(13) . . ?
N1B C36 C30 121.3(13) . . ?
N2B C36 C30 123.3(13) . . ?
C38 C37 C42 128.3(16) . . ?
C38 C37 N1B 128.0(15) . . ?
C42 C37 N1B 103.3(13) . . ?
C37 C38 C39 118.2(16) . . ?
C37 C38 H41 120.9 . . ?
C39 C38 H41 120.9 . . ?
C38 C39 C40 115.4(14) . . ?
C38 C39 H40 122.3 . . ?
C40 C39 H40 122.3 . . ?
C41 C40 C39 125.5(14) . . ?
C41 C40 H39 117.3 . . ?
C39 C40 H39 117.3 . . ?
C40 C41 C42 115.6(15) . . ?
C40 C41 H38 122.2 . . ?
C42 C41 H38 122.2 . . ?
C37 C42 N2B 115.8(13) . . ?
C37 C42 C41 116.3(14) . . ?
N2B C42 C41 127.8(13) . . ?
O5 C43 O6 127.1(18) . . ?
O5 C43 C44 120.9(18) . . ?
O6 C43 C44 111(2) . . ?
C43 C44 H1A1 109.5 . . ?
C43 C44 H1A2 109.5 . . ?
H1A1 C44 H1A2 109.5 . . ?
C43 C44 H1A3 109.5 . . ?
H1A1 C44 H1A3 109.5 . . ?
H1A2 C44 H1A3 109.5 . . ?
N3B C45 C46 127.9(13) . . ?
N3B C45 H11 116.1 . . ?
C46 C45 H11 116.1 . . ?
C55 C46 C47 122.7(15) . . ?
C55 C46 C45 120.9(15) . . ?
C47 C46 C45 114.9(14) . . ?
C48 C47 C46 120.9(14) . . ?
C48 C47 H7 119.5 . . ?
C46 C47 H7 119.5 . . ?
C47 C48 C49 123.2(15) . . ?
C47 C48 H6 118.4 . . ?
C49 C48 H6 118.4 . . ?
N5 C49 C50 126.1(14) . . ?
N5 C49 C48 119.6(14) . . ?
C50 C49 C48 113.6(15) . . ?
C49 C50 C55 122.7(15) . . ?
C49 C50 H10 118.7 . . ?
C55 C50 H10 118.7 . . ?
N5 C51 C52 105.2(12) . . ?
N5 C51 H4A 110.7 . . ?
C52 C51 H4A 110.7 . . ?
N5 C51 H4B 110.7 . . ?
C52 C51 H4B 110.7 . . ?
H4A C51 H4B 108.8 . . ?
C51 C52 H3A 109.5 . . ?
C51 C52 H3B 109.5 . . ?
H3A C52 H3B 109.5 . . ?
C51 C52 H3C 109.5 . . ?
H3A C52 H3C 109.5 . . ?
H3B C52 H3C 109.5 . . ?
N5 C53 C54 108.6(17) . . ?
N5 C53 H2A 110.0 . . ?
C54 C53 H2A 110.0 . . ?
N5 C53 H2B 110.0 . . ?
C54 C53 H2B 110.0 . . ?
H2A C53 H2B 108.4 . . ?
C53 C54 H1A 109.5 . . ?
C53 C54 H1B 109.5 . . ?
H1A C54 H1B 109.5 . . ?
C53 C54 H1C 109.5 . . ?
H1A C54 H1C 109.5 . . ?
H1B C54 H1C 109.5 . . ?
O4 C55 C46 129.5(14) . . ?
O4 C55 C50 114.4(13) . . ?
C46 C55 C50 116.0(14) . . ?
C5 N4 C2 123.6(12) . . ?
C5 N4 C4 114.1(13) . . ?
C2 N4 C4 120.8(13) . . ?
C19 N1A C18 111.0(12) . . ?
C19 N1A H8 124.5 . . ?
C18 N1A H8 124.5 . . ?
C24 N2A C18 113.2(11) . . ?
C24 N2A Zn2 129.1(10) . . ?
C18 N2A Zn2 117.7(9) . . ?
C11 N3A C12 119.1(12) . . ?
C11 N3A Zn2 119.4(9) . . ?
C12 N3A Zn2 121.3(10) . . ?
C49 N5 C53 126.0(15) . . ?
C49 N5 C51 117.5(13) . . ?
C53 N5 C51 114.4(14) . . ?
C36 N2B C42 98.6(11) . . ?
C36 N2B Zn1 125.9(9) . . ?
C42 N2B Zn1 134.7(9) . . ?
C36 N1B C37 106.7(12) . . ?
C36 N1B H5 126.6 . . ?
C37 N1B H5 126.6 . . ?
C45 N3B C35 117.7(12) . . ?
C45 N3B Zn1 121.5(9) . . ?
C35 N3B Zn1 120.7(10) . . ?
C25 O3 Zn2 99.7(10) . . ?
C25 O2 Zn2 85.5(10) . . ?
C7 O1 Zn2 128.8(9) . . ?
C55 O4 Zn1 123.5(9) . . ?
C43 O5 Zn1 79.2(11) . . ?
C43 O6 Zn1 90.0(12) . . ?
C29 O7 H4A1 109.5 . . ?
O4 Zn1 N2B 127.8(5) . . ?
O4 Zn1 N3B 94.2(5) . . ?
N2B Zn1 N3B 90.5(4) . . ?
O4 Zn1 O6 116.5(5) . . ?
N2B Zn1 O6 111.5(5) . . ?
N3B Zn1 O6 107.0(5) . . ?
O4 Zn1 O5 88.6(4) . . ?
N2B Zn1 O5 95.9(5) . . ?
N3B Zn1 O5 169.4(5) . . ?
O6 Zn1 O5 62.8(5) . . ?
O1 Zn2 O3 110.6(5) . . ?
O1 Zn2 N2A 128.6(5) . . ?
O3 Zn2 N2A 115.5(5) . . ?
O1 Zn2 N3A 95.2(5) . . ?
O3 Zn2 N3A 109.6(5) . . ?
N2A Zn2 N3A 89.8(5) . . ?
O1 Zn2 O2 88.7(4) . . ?
O3 Zn2 O2 57.0(5) . . ?
N2A Zn2 O2 97.9(4) . . ?
N3A Zn2 O2 166.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 C7 -1(3) . . . . ?
N4 C5 C6 C7 -174.8(15) . . . . ?
C5 C6 C7 O1 -174.4(15) . . . . ?
C5 C6 C7 C8 8(2) . . . . ?
C6 C7 C8 C11 174.6(16) . . . . ?
O1 C7 C8 C11 -3(2) . . . . ?
C6 C7 C8 C9 -11(2) . . . . ?
O1 C7 C8 C9 171.4(14) . . . . ?
C11 C8 C9 C10 -176.0(17) . . . . ?
C7 C8 C9 C10 9(3) . . . . ?
C8 C9 C10 C5 -3(3) . . . . ?
N4 C5 C10 C9 171.3(17) . . . . ?
C6 C5 C10 C9 -2(3) . . . . ?
C9 C8 C11 N3A -175.7(15) . . . . ?
C7 C8 C11 N3A -2(3) . . . . ?
N3A C12 C13 C14 -175.9(14) . . . . ?
C17 C12 C13 C14 -2(2) . . . . ?
C12 C13 C14 C15 -7(3) . . . . ?
C13 C14 C15 C16 9(3) . . . . ?
C14 C15 C16 C17 -3(3) . . . . ?
C15 C16 C17 C18 -175.4(16) . . . . ?
C15 C16 C17 C12 -4(2) . . . . ?
N3A C12 C17 C16 -179.0(14) . . . . ?
C13 C12 C17 C16 7(2) . . . . ?
N3A C12 C17 C18 -9(2) . . . . ?
C13 C12 C17 C18 177.2(15) . . . . ?
C16 C17 C18 N2A -156.7(16) . . . . ?
C12 C17 C18 N2A 33(3) . . . . ?
C16 C17 C18 N1A 21(2) . . . . ?
C12 C17 C18 N1A -148.6(15) . . . . ?
N1A C19 C20 C21 179.6(18) . . . . ?
C24 C19 C20 C21 7(2) . . . . ?
C19 C20 C21 C22 -7(3) . . . . ?
C20 C21 C22 C23 3(3) . . . . ?
C21 C22 C23 C24 2(2) . . . . ?
C22 C23 C24 N2A -177.7(15) . . . . ?
C22 C23 C24 C19 -2(2) . . . . ?
N1A C19 C24 N2A -0.7(15) . . . . ?
C20 C19 C24 N2A 174.1(15) . . . . ?
N1A C19 C24 C23 -177.8(13) . . . . ?
C20 C19 C24 C23 -3(2) . . . . ?
C35 C30 C31 C32 -3(2) . . . . ?
C36 C30 C31 C32 -178.1(15) . . . . ?
C30 C31 C32 C33 -5(3) . . . . ?
C31 C32 C33 C34 9(3) . . . . ?
C32 C33 C34 C35 -5(2) . . . . ?
C33 C34 C35 C30 -2(2) . . . . ?
C33 C34 C35 N3B 179.6(14) . . . . ?
C31 C30 C35 C34 6(2) . . . . ?
C36 C30 C35 C34 -179.2(13) . . . . ?
C31 C30 C35 N3B -175.3(13) . . . . ?
C36 C30 C35 N3B -1(2) . . . . ?
C35 C30 C36 N1B 157.8(13) . . . . ?
C31 C30 C36 N1B -27(2) . . . . ?
C35 C30 C36 N2B -26(2) . . . . ?
C31 C30 C36 N2B 148.4(14) . . . . ?
C42 C37 C38 C39 11(3) . . . . ?
N1B C37 C38 C39 -178.4(16) . . . . ?
C37 C38 C39 C40 -9(3) . . . . ?
C38 C39 C40 C41 3(3) . . . . ?
C39 C40 C41 C42 2(2) . . . . ?
C38 C37 C42 N2B 176.1(17) . . . . ?
N1B C37 C42 N2B 3.5(17) . . . . ?
C38 C37 C42 C41 -5(3) . . . . ?
N1B C37 C42 C41 -178.0(13) . . . . ?
C40 C41 C42 C37 -1(2) . . . . ?
C40 C41 C42 N2B 177.3(14) . . . . ?
N3B C45 C46 C55 -11(2) . . . . ?
N3B C45 C46 C47 -178.0(17) . . . . ?
C55 C46 C47 C48 9(3) . . . . ?
C45 C46 C47 C48 175.4(16) . . . . ?
C46 C47 C48 C49 -10(3) . . . . ?
C47 C48 C49 N5 -179.9(19) . . . . ?
C47 C48 C49 C50 9(3) . . . . ?
N5 C49 C50 C55 -176.6(16) . . . . ?
C48 C49 C50 C55 -6(2) . . . . ?
C47 C46 C55 O4 176.2(16) . . . . ?
C45 C46 C55 O4 11(2) . . . . ?
C47 C46 C55 C50 -6(2) . . . . ?
C45 C46 C55 C50 -171.6(13) . . . . ?
C49 C50 C55 O4 -177.1(15) . . . . ?
C49 C50 C55 C46 5(2) . . . . ?
C10 C5 N4 C2 171.1(17) . . . . ?
C6 C5 N4 C2 -16(2) . . . . ?
C10 C5 N4 C4 5(2) . . . . ?
C6 C5 N4 C4 178.5(14) . . . . ?
C1 C2 N4 C5 -76.4(19) . . . . ?
C1 C2 N4 C4 88.5(17) . . . . ?
C3 C4 N4 C5 73.7(19) . . . . ?
C3 C4 N4 C2 -92.6(19) . . . . ?
C20 C19 N1A C18 -174.2(19) . . . . ?
C24 C19 N1A C18 -0.8(16) . . . . ?
N2A C18 N1A C19 2.1(17) . . . . ?
C17 C18 N1A C19 -176.4(14) . . . . ?
C23 C24 N2A C18 178.6(16) . . . . ?
C19 C24 N2A C18 2.0(15) . . . . ?
C23 C24 N2A Zn2 3(2) . . . . ?
C19 C24 N2A Zn2 -174.1(10) . . . . ?
N1A C18 N2A C24 -2.6(16) . . . . ?
C17 C18 N2A C24 175.7(15) . . . . ?
N1A C18 N2A Zn2 174.0(9) . . . . ?
C17 C18 N2A Zn2 -8(2) . . . . ?
C8 C11 N3A C12 -174.5(14) . . . . ?
C8 C11 N3A Zn2 11(2) . . . . ?
C13 C12 N3A C11 -34(2) . . . . ?
C17 C12 N3A C11 152.0(14) . . . . ?
C13 C12 N3A Zn2 140.5(12) . . . . ?
C17 C12 N3A Zn2 -33.7(17) . . . . ?
C50 C49 N5 C53 -176.5(19) . . . . ?
C48 C49 N5 C53 13(3) . . . . ?
C50 C49 N5 C51 -14(3) . . . . ?
C48 C49 N5 C51 175.6(15) . . . . ?
C54 C53 N5 C49 -92(2) . . . . ?
C54 C53 N5 C51 104.7(18) . . . . ?
C52 C51 N5 C49 87.9(17) . . . . ?
C52 C51 N5 C53 -107.7(18) . . . . ?
N1B C36 N2B C42 -3.3(16) . . . . ?
C30 C36 N2B C42 -179.2(14) . . . . ?
N1B C36 N2B Zn1 -174.6(10) . . . . ?
C30 C36 N2B Zn1 9(2) . . . . ?
C37 C42 N2B C36 -0.4(17) . . . . ?
C41 C42 N2B C36 -178.7(16) . . . . ?
C37 C42 N2B Zn1 169.7(12) . . . . ?
C41 C42 N2B Zn1 -9(2) . . . . ?
N2B C36 N1B C37 5.5(18) . . . . ?
C30 C36 N1B C37 -178.4(13) . . . . ?
C38 C37 N1B C36 -177.8(18) . . . . ?
C42 C37 N1B C36 -5.2(16) . . . . ?
C46 C45 N3B C35 -178.4(14) . . . . ?
C46 C45 N3B Zn1 -2(2) . . . . ?
C34 C35 N3B C45 34(2) . . . . ?
C30 C35 N3B C45 -144.4(14) . . . . ?
C34 C35 N3B Zn1 -142.1(12) . . . . ?
C30 C35 N3B Zn1 39.5(16) . . . . ?
O2 C25 O3 Zn2 5.2(16) . . . . ?
C26 C25 O3 Zn2 -179.3(15) . . . . ?
O3 C25 O2 Zn2 -4.4(14) . . . . ?
C26 C25 O2 Zn2 179.8(15) . . . . ?
C6 C7 O1 Zn2 178.7(12) . . . . ?
C8 C7 O1 Zn2 -4.0(17) . . . . ?
C46 C55 O4 Zn1 4(2) . . . . ?
C50 C55 O4 Zn1 -173.6(9) . . . . ?
O6 C43 O5 Zn1 -9.5(18) . . . . ?
C44 C43 O5 Zn1 -178.6(18) . . . . ?
O5 C43 O6 Zn1 11(2) . . . . ?
C44 C43 O6 Zn1 -179.5(13) . . . . ?
C55 O4 Zn1 N2B -107.2(11) . . . . ?
C55 O4 Zn1 N3B -13.3(11) . . . . ?
C55 O4 Zn1 O6 98.0(11) . . . . ?
C55 O4 Zn1 O5 156.5(11) . . . . ?
C36 N2B Zn1 O4 115.2(12) . . . . ?
C42 N2B Zn1 O4 -52.7(15) . . . . ?
C36 N2B Zn1 N3B 19.5(13) . . . . ?
C42 N2B Zn1 N3B -148.4(14) . . . . ?
C36 N2B Zn1 O6 -89.0(13) . . . . ?
C42 N2B Zn1 O6 103.1(14) . . . . ?
C36 N2B Zn1 O5 -152.0(12) . . . . ?
C42 N2B Zn1 O5 40.1(14) . . . . ?
C45 N3B Zn1 O4 12.2(13) . . . . ?
C35 N3B Zn1 O4 -171.9(10) . . . . ?
C45 N3B Zn1 N2B 140.1(12) . . . . ?
C35 N3B Zn1 N2B -43.9(11) . . . . ?
C45 N3B Zn1 O6 -107.2(12) . . . . ?
C35 N3B Zn1 O6 68.8(11) . . . . ?
C45 N3B Zn1 O5 -93(3) . . . . ?
C35 N3B Zn1 O5 83(3) . . . . ?
C43 O6 Zn1 O4 68.2(10) . . . . ?
C43 O6 Zn1 N2B -90.6(10) . . . . ?
C43 O6 Zn1 N3B 172.0(9) . . . . ?
C43 O6 Zn1 O5 -5.1(9) . . . . ?
C43 O5 Zn1 O4 -115.6(12) . . . . ?
C43 O5 Zn1 N2B 116.5(12) . . . . ?
C43 O5 Zn1 N3B -10(3) . . . . ?
C43 O5 Zn1 O6 5.3(10) . . . . ?
C7 O1 Zn2 O3 -103.3(12) . . . . ?
C7 O1 Zn2 N2A 103.8(12) . . . . ?
C7 O1 Zn2 N3A 9.9(12) . . . . ?
C7 O1 Zn2 O2 -157.1(12) . . . . ?
C25 O3 Zn2 O1 -77.0(10) . . . . ?
C25 O3 Zn2 N2A 79.8(11) . . . . ?
C25 O3 Zn2 N3A 179.3(9) . . . . ?
C25 O3 Zn2 O2 -2.8(9) . . . . ?
C24 N2A Zn2 O1 56.4(14) . . . . ?
C18 N2A Zn2 O1 -119.5(10) . . . . ?
C24 N2A Zn2 O3 -95.3(12) . . . . ?
C18 N2A Zn2 O3 88.7(11) . . . . ?
C24 N2A Zn2 N3A 153.0(12) . . . . ?
C18 N2A Zn2 N3A -23.0(11) . . . . ?
C24 N2A Zn2 O2 -38.2(13) . . . . ?
C18 N2A Zn2 O2 145.8(10) . . . . ?
C11 N3A Zn2 O1 -12.7(11) . . . . ?
C12 N3A Zn2 O1 173.0(11) . . . . ?
C11 N3A Zn2 O3 101.4(11) . . . . ?
C12 N3A Zn2 O3 -73.0(11) . . . . ?
C11 N3A Zn2 N2A -141.5(11) . . . . ?
C12 N3A Zn2 N2A 44.2(11) . . . . ?
C11 N3A Zn2 O2 94(2) . . . . ?
C12 N3A Zn2 O2 -81(2) . . . . ?
C25 O2 Zn2 O1 118.6(9) . . . . ?
C25 O2 Zn2 O3 2.9(9) . . . . ?
C25 O2 Zn2 N2A -112.5(9) . . . . ?
C25 O2 Zn2 N3A 12(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.070
