# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1434846'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '[L4ZnEt]'
_chemical_name_common            4
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H37 N3 Zn'
_chemical_formula_sum            'C26 H37 N3 Zn'
_chemical_formula_weight         456.96

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'
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   'P 21/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                   8.8377(8)
_cell_length_b                   34.635(3)
_cell_length_c                   9.0028(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.1850(10)
_cell_angle_gamma                90.00
_cell_volume                     2428.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8208
_exptl_absorpt_correction_T_max  0.9504
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15366
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4249
_reflns_number_gt                3308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0495P)²+1.4854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4249
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6440(4) 0.91781(8) 0.9606(3) 0.0239(6) Uani 1 1 d . . .
C2 C 0.6458(4) 0.92135(8) 1.1170(4) 0.0306(7) Uani 1 1 d . . .
C3 C 0.5086(5) 0.90437(10) 1.1521(4) 0.0437(9) Uani 1 1 d . . .
H3 H 0.4311 0.8881 1.0534 0.052 Uiso 1 1 calc R . .
C4 C 0.5878(6) 0.87840(11) 1.3103(5) 0.0593(11) Uani 1 1 d . . .
H4A H 0.4961 0.8675 1.3294 0.089 Uiso 1 1 calc R . .
H4B H 0.6652 0.8938 1.4083 0.089 Uiso 1 1 calc R . .
H4C H 0.6525 0.8574 1.2935 0.089 Uiso 1 1 calc R . .
C5 C 0.4003(5) 0.93616(13) 1.1749(5) 0.0624(12) Uani 1 1 d . . .
H5A H 0.3124 0.9243 1.1974 0.094 Uiso 1 1 calc R . .
H5B H 0.3449 0.9517 1.0720 0.094 Uiso 1 1 calc R . .
H5C H 0.4746 0.9527 1.2700 0.094 Uiso 1 1 calc R . .
C6 C 0.7788(4) 0.94235(9) 1.2439(4) 0.0355(8) Uani 1 1 d . . .
H6 H 0.7818 0.9450 1.3503 0.043 Uiso 1 1 calc R . .
C7 C 0.9054(4) 0.95930(9) 1.2192(4) 0.0357(8) Uani 1 1 d . . .
H7 H 0.9934 0.9738 1.3070 0.043 Uiso 1 1 calc R . .
C8 C 0.9042(4) 0.95515(8) 1.0661(4) 0.0326(7) Uani 1 1 d . . .
H8 H 0.9936 0.9664 1.0503 0.039 Uiso 1 1 calc R . .
C9 C 0.7745(4) 0.93480(8) 0.9348(4) 0.0255(7) Uani 1 1 d . . .
C10 C 0.7750(4) 0.93217(9) 0.7659(4) 0.0330(7) Uani 1 1 d . . .
H10 H 0.7128 0.9081 0.7073 0.040 Uiso 1 1 calc R . .
C11 C 0.6813(5) 0.96692(10) 0.6545(4) 0.0457(9) Uani 1 1 d . . .
H11A H 0.6826 0.9648 0.5466 0.069 Uiso 1 1 calc R . .
H11B H 0.7391 0.9908 0.7113 0.069 Uiso 1 1 calc R . .
H11C H 0.5622 0.9673 0.6344 0.069 Uiso 1 1 calc R . .
C12 C 0.9557(4) 0.93073(10) 0.7837(4) 0.0431(9) Uani 1 1 d . . .
H12A H 0.9481 0.9291 0.6717 0.065 Uiso 1 1 calc R . .
H12B H 1.0162 0.9080 0.8500 0.065 Uiso 1 1 calc R . .
H12C H 1.0186 0.9541 0.8409 0.065 Uiso 1 1 calc R . .
C13 C 0.3360(4) 0.95435(9) 0.7365(4) 0.0371(8) Uani 1 1 d . . .
H13A H 0.4280 0.9641 0.8432 0.056 Uiso 1 1 calc R . .
H13B H 0.2263 0.9558 0.7386 0.056 Uiso 1 1 calc R . .
H13C H 0.3298 0.9701 0.6433 0.056 Uiso 1 1 calc R . .
C14 C 0.3730(4) 0.91282(8) 0.7121(4) 0.0297(7) Uani 1 1 d . . .
C15 C 0.2497(4) 0.89508(9) 0.5643(4) 0.0362(8) Uani 1 1 d . . .
H15 H 0.1464 0.9092 0.5029 0.043 Uiso 1 1 calc R . .
C16 C 0.2569(4) 0.85929(9) 0.4937(4) 0.0368(8) Uani 1 1 d . . .
C17 C 0.1239(5) 0.85284(11) 0.3112(4) 0.0562(11) Uani 1 1 d . . .
H17A H 0.1399 0.8272 0.2751 0.084 Uiso 1 1 calc R . .
H17B H 0.1374 0.8725 0.2401 0.084 Uiso 1 1 calc R . .
H17C H 0.0086 0.8547 0.3007 0.084 Uiso 1 1 calc R . .
C18 C 0.3845(5) 0.79850(9) 0.4849(4) 0.0472(9) Uani 1 1 d . . .
H18A H 0.3986 0.8068 0.3870 0.057 Uiso 1 1 calc R . .
H18B H 0.2769 0.7834 0.4422 0.057 Uiso 1 1 calc R . .
C19 C 0.5356(5) 0.77312(9) 0.5995(5) 0.0488(10) Uani 1 1 d . . .
H19A H 0.5183 0.7644 0.6951 0.059 Uiso 1 1 calc R . .
H19B H 0.5362 0.7499 0.5357 0.059 Uiso 1 1 calc R . .
C20 C 0.7066(5) 0.79231(9) 0.6679(4) 0.0416(9) Uani 1 1 d . . .
C21 C 0.8265(6) 0.78317(12) 0.6151(5) 0.0637(12) Uani 1 1 d . . .
H21 H 0.8005 0.7641 0.5307 0.076 Uiso 1 1 calc R . .
C22 C 0.9825(7) 0.80160(14) 0.6845(6) 0.0761(14) Uani 1 1 d . . .
H22 H 1.0643 0.7956 0.6477 0.091 Uiso 1 1 calc R . .
C23 C 1.0187(5) 0.82868(12) 0.8068(6) 0.0624(12) Uani 1 1 d . . .
H23 H 1.1261 0.8417 0.8575 0.075 Uiso 1 1 calc R . .
C24 C 0.8948(4) 0.83661(10) 0.8546(4) 0.0420(8) Uani 1 1 d . . .
H24 H 0.9202 0.8553 0.9403 0.050 Uiso 1 1 calc R . .
C25 C 0.5153(5) 0.80159(9) 0.9938(4) 0.0431(9) Uani 1 1 d . . .
H25A H 0.4549 0.8149 1.0479 0.052 Uiso 1 1 calc R . .
H25B H 0.4462 0.7787 0.9341 0.052 Uiso 1 1 calc R . .
C26 C 0.6889(6) 0.78808(11) 1.1300(5) 0.0644(12) Uani 1 1 d . . .
H26A H 0.6730 0.7709 1.2079 0.097 Uiso 1 1 calc R . .
H26B H 0.7575 0.8105 1.1918 0.097 Uiso 1 1 calc R . .
H26C H 0.7485 0.7741 1.0781 0.097 Uiso 1 1 calc R . .
N1 N 0.5135(3) 0.89541(7) 0.8272(3) 0.0249(5) Uani 1 1 d . . .
N2 N 0.3721(3) 0.83263(7) 0.5751(3) 0.0350(6) Uani 1 1 d . . .
N3 N 0.7422(3) 0.81953(7) 0.7877(3) 0.0335(6) Uani 1 1 d . . .
Zn1 Zn 0.52685(5) 0.837103(9) 0.82499(4) 0.02935(13) 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 1.406(4) . ?
C1 C9 1.408(4) . ?
C1 N1 1.438(3) . ?
C2 C6 1.396(4) . ?
C2 C3 1.509(4) . ?
C3 C5 1.535(5) . ?
C3 C4 1.545(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.526(4) . ?
C10 C12 1.528(4) . ?
C10 C11 1.535(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.328(4) . ?
C14 C15 1.402(4) . ?
C15 C16 1.408(4) . ?
C15 H15 0.9500 . ?
C16 N2 1.312(4) . ?
C16 C17 1.518(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.467(4) . ?
C18 C19 1.522(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.492(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N3 1.353(4) . ?
C20 C21 1.388(5) . ?
C21 C22 1.373(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.364(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(5) . ?
C23 H23 0.9500 . ?
C24 N3 1.328(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.517(5) . ?
C25 Zn1 1.995(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 Zn1 2.023(2) . ?
N2 Zn1 2.012(2) . ?
N3 Zn1 2.170(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
C2 C1 C9 120.4(3) . . ?
C2 C1 N1 120.6(3) . . ?
C9 C1 N1 118.9(2) . . ?
C6 C2 C1 118.1(3) . . ?
C6 C2 C3 118.8(3) . . ?
C1 C2 C3 123.1(3) . . ?
C2 C3 C5 111.2(3) . . ?
C2 C3 C4 111.1(3) . . ?
C5 C3 C4 109.5(3) . . ?
C2 C3 H3 108.3 . . ?
C5 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C2 C6 H6 119.1 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C1 118.9(3) . . ?
C8 C9 C10 119.2(3) . . ?
C1 C9 C10 121.9(3) . . ?
C9 C10 C12 113.1(3) . . ?
C9 C10 C11 110.5(2) . . ?
C12 C10 C11 108.0(3) . . ?
C9 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 124.2(3) . . ?
N1 C14 C13 120.3(3) . . ?
C15 C14 C13 115.5(3) . . ?
C14 C15 C16 129.3(3) . . ?
C14 C15 H15 115.3 . . ?
C16 C15 H15 115.3 . . ?
N2 C16 C15 123.8(3) . . ?
N2 C16 C17 120.1(3) . . ?
C15 C16 C17 116.2(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 111.2(3) . . ?
N2 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N2 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 114.6(3) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
N3 C20 C21 120.3(4) . . ?
N3 C20 C19 116.7(3) . . ?
C21 C20 C19 123.0(3) . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.3(4) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 118.1(4) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
N3 C24 C23 123.7(4) . . ?
N3 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
C26 C25 Zn1 114.2(3) . . ?
C26 C25 H25A 108.7 . . ?
Zn1 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
Zn1 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C14 N1 C1 119.5(2) . . ?
C14 N1 Zn1 118.88(19) . . ?
C1 N1 Zn1 121.29(17) . . ?
C16 N2 C18 119.9(3) . . ?
C16 N2 Zn1 120.6(2) . . ?
C18 N2 Zn1 119.4(2) . . ?
C24 N3 C20 118.4(3) . . ?
C24 N3 Zn1 125.6(2) . . ?
C20 N3 Zn1 115.3(2) . . ?
C25 Zn1 N2 123.49(12) . . ?
C25 Zn1 N1 125.72(12) . . ?
N2 Zn1 N1 94.34(9) . . ?
C25 Zn1 N3 108.01(13) . . ?
N2 Zn1 N3 89.33(11) . . ?
N1 Zn1 N3 109.91(10) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.056
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic, Oxygen-sensitive'
####################################################################### 
# 
# 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 1434847'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H70 N6 Zn2'
_chemical_formula_sum            'C50 H70 N6 Zn2'
_chemical_formula_weight         885.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6519(7)
_cell_length_b                   9.7012(7)
_cell_length_c                   14.3904(11)
_cell_angle_alpha                76.206(3)
_cell_angle_beta                 88.607(3)
_cell_angle_gamma                63.321(3)
_cell_volume                     1163.94(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_T_max  0.7833
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9718
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4053
_reflns_number_gt                3762
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0428P)²+1.0527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4053
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7973(2) 0.8180(3) 0.83742(15) 0.0226(5) Uani 1 1 d . . .
C2 C 0.8390(3) 0.9280(3) 0.86146(16) 0.0265(5) Uani 1 1 d . . .
C3 C 0.9211(3) 1.0065(3) 0.79392(18) 0.0328(6) Uani 1 1 d . . .
H3 H 0.8897 1.0127 0.7267 0.039 Uiso 1 1 calc R . .
C4 C 1.0978(3) 0.9053(4) 0.8125(2) 0.0470(7) Uani 1 1 d . . .
H4A H 1.1487 0.9575 0.7680 0.070 Uiso 1 1 calc R . .
H4B H 1.1267 0.7996 0.8025 0.070 Uiso 1 1 calc R . .
H4C H 1.1313 0.8938 0.8788 0.070 Uiso 1 1 calc R . .
C5 C 0.8771(4) 1.1767(4) 0.8004(2) 0.0474(7) Uani 1 1 d . . .
H5A H 0.9333 1.2210 0.7552 0.071 Uiso 1 1 calc R . .
H5B H 0.9053 1.1743 0.8659 0.071 Uiso 1 1 calc R . .
H5C H 0.7647 1.2433 0.7841 0.071 Uiso 1 1 calc R . .
C6 C 0.8058(3) 0.9612(3) 0.95111(18) 0.0364(6) Uani 1 1 d . . .
H6 H 0.8350 1.0333 0.9690 0.044 Uiso 1 1 calc R . .
C7 C 0.7318(3) 0.8915(3) 1.01396(18) 0.0391(6) Uani 1 1 d . . .
H7 H 0.7098 0.9160 1.0744 0.047 Uiso 1 1 calc R . .
C8 C 0.6898(3) 0.7863(3) 0.98903(17) 0.0343(6) Uani 1 1 d . . .
H8 H 0.6376 0.7398 1.0324 0.041 Uiso 1 1 calc R . .
C9 C 0.7222(3) 0.7465(3) 0.90124(16) 0.0259(5) Uani 1 1 d . . .
C10 C 0.6714(3) 0.6317(3) 0.87581(18) 0.0327(6) Uani 1 1 d . . .
H10 H 0.7179 0.6060 0.8155 0.039 Uiso 1 1 calc R . .
C11 C 0.4940(3) 0.7119(4) 0.8553(2) 0.0491(7) Uani 1 1 d . . .
H11A H 0.4623 0.6372 0.8388 0.074 Uiso 1 1 calc R . .
H11B H 0.4608 0.8070 0.8014 0.074 Uiso 1 1 calc R . .
H11C H 0.4454 0.7428 0.9125 0.074 Uiso 1 1 calc R . .
C12 C 0.7277(4) 0.4745(4) 0.9538(2) 0.0467(7) Uani 1 1 d . . .
H12A H 0.6923 0.4049 0.9337 0.070 Uiso 1 1 calc R . .
H12B H 0.6849 0.4964 1.0141 0.070 Uiso 1 1 calc R . .
H12C H 0.8417 0.4216 0.9634 0.070 Uiso 1 1 calc R . .
C13 C 1.0598(3) 0.5417(3) 0.81683(18) 0.0368(6) Uani 1 1 d . . .
H13A H 1.0177 0.5700 0.8760 0.055 Uiso 1 1 calc R . .
H13B H 1.1639 0.5355 0.8139 0.055 Uiso 1 1 calc R . .
H13C H 1.0665 0.4381 0.8163 0.055 Uiso 1 1 calc R . .
C14 C 0.9536(2) 0.6677(3) 0.73068(16) 0.0223(5) Uani 1 1 d . . .
C15 C 0.9997(2) 0.6436(3) 0.64022(16) 0.0236(5) Uani 1 1 d . . .
H15 H 1.0914 0.5475 0.6419 0.028 Uiso 1 1 calc R . .
C16 C 0.9312(2) 0.7393(3) 0.54709(16) 0.0205(4) Uani 1 1 d . . .
C17 C 1.0216(3) 0.6803(3) 0.46502(17) 0.0308(5) Uani 1 1 d . . .
H17A H 0.9654 0.7541 0.4036 0.046 Uiso 1 1 calc R . .
H17B H 1.0327 0.5740 0.4673 0.046 Uiso 1 1 calc R . .
H17C H 1.1250 0.6747 0.4711 0.046 Uiso 1 1 calc R . .
C18 C 0.7340(3) 0.9514(3) 0.42792(16) 0.0267(5) Uani 1 1 d . . .
H18A H 0.6752 0.9002 0.4079 0.032 Uiso 1 1 calc R . .
H18B H 0.8210 0.9363 0.3870 0.032 Uiso 1 1 calc R . .
C19 C 0.3720(2) 0.8728(3) 0.58739(15) 0.0226(5) Uani 1 1 d . . .
C20 C 0.3104(3) 0.7703(3) 0.58102(18) 0.0319(5) Uani 1 1 d . . .
H20 H 0.2016 0.8113 0.5662 0.038 Uiso 1 1 calc R . .
C21 C 0.4072(3) 0.6092(3) 0.5962(2) 0.0361(6) Uani 1 1 d . . .
H21 H 0.3664 0.5377 0.5926 0.043 Uiso 1 1 calc R . .
C22 C 0.5651(3) 0.5542(3) 0.61670(18) 0.0310(5) Uani 1 1 d . . .
H22 H 0.6352 0.4441 0.6265 0.037 Uiso 1 1 calc R . .
C23 C 0.6188(3) 0.6611(3) 0.62261(16) 0.0254(5) Uani 1 1 d . . .
H23 H 0.7275 0.6221 0.6368 0.031 Uiso 1 1 calc R . .
C24 C 0.5344(3) 1.1697(3) 0.64898(17) 0.0277(5) Uani 1 1 d . . .
H24A H 0.6053 1.2181 0.6496 0.033 Uiso 1 1 calc R . .
H24B H 0.4589 1.2330 0.5914 0.033 Uiso 1 1 calc R . .
C25 C 0.4437(3) 1.1889(3) 0.73777(19) 0.0403(7) Uani 1 1 d . . .
H25A H 0.3873 1.3022 0.7367 0.060 Uiso 1 1 calc R . .
H25B H 0.5164 1.1308 0.7960 0.060 Uiso 1 1 calc R . .
H25C H 0.3692 1.1459 0.7375 0.060 Uiso 1 1 calc R . .
N1 N 0.8241(2) 0.7905(2) 0.74284(12) 0.0208(4) Uani 1 1 d . . .
N2 N 0.79783(19) 0.8728(2) 0.52931(12) 0.0192(4) Uani 1 1 d . . .
N3 N 0.5253(2) 0.8190(2) 0.60937(13) 0.0209(4) Uani 1 1 d . . .
Zn1 Zn 0.66041(3) 0.94989(3) 0.632856(17) 0.01901(10) 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 C9 1.402(3) . ?
C1 C2 1.410(3) . ?
C1 N1 1.444(3) . ?
C2 C6 1.399(3) . ?
C2 C3 1.518(3) . ?
C3 C4 1.529(4) . ?
C3 C5 1.535(4) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.519(4) . ?
C10 C11 1.531(4) . ?
C10 C12 1.533(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.515(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.328(3) . ?
C14 C15 1.404(3) . ?
C15 C16 1.412(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.327(3) . ?
C16 C17 1.519(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.477(3) . ?
C18 C19 1.507(3) 2_676 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N3 1.346(3) . ?
C19 C20 1.388(3) . ?
C19 C18 1.507(3) 2_676 ?
C20 C21 1.378(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(3) . ?
C22 H22 0.9500 . ?
C23 N3 1.350(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.532(3) . ?
C24 Zn1 1.994(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 Zn1 2.0379(17) . ?
N2 Zn1 2.0208(17) . ?
N3 Zn1 2.2672(18) . ?

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
C9 C1 C2 120.6(2) . . ?
C9 C1 N1 121.2(2) . . ?
C2 C1 N1 118.0(2) . . ?
C6 C2 C1 118.1(2) . . ?
C6 C2 C3 120.1(2) . . ?
C1 C2 C3 121.7(2) . . ?
C2 C3 C4 110.7(2) . . ?
C2 C3 C5 113.2(2) . . ?
C4 C3 C5 109.5(2) . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C5 C3 H3 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C2 C6 H6 119.3 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C1 118.6(2) . . ?
C8 C9 C10 119.7(2) . . ?
C1 C9 C10 121.7(2) . . ?
C9 C10 C11 110.0(2) . . ?
C9 C10 C12 112.8(2) . . ?
C11 C10 C12 110.5(2) . . ?
C9 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C12 C10 H10 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 123.6(2) . . ?
N1 C14 C13 120.4(2) . . ?
C15 C14 C13 116.01(19) . . ?
C14 C15 C16 130.3(2) . . ?
C14 C15 H15 114.9 . . ?
C16 C15 H15 114.9 . . ?
N2 C16 C15 124.10(19) . . ?
N2 C16 C17 120.47(19) . . ?
C15 C16 C17 115.43(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 112.06(18) . 2_676 ?
N2 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 2_676 . ?
N2 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 2_676 . ?
H18A C18 H18B 107.9 . . ?
N3 C19 C20 121.7(2) . . ?
N3 C19 C18 118.3(2) . 2_676 ?
C20 C19 C18 120.0(2) . 2_676 ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 118.4(2) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N3 C23 C22 123.4(2) . . ?
N3 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?
C25 C24 Zn1 118.03(17) . . ?
C25 C24 H24A 107.8 . . ?
Zn1 C24 H24A 107.8 . . ?
C25 C24 H24B 107.8 . . ?
Zn1 C24 H24B 107.8 . . ?
H24A C24 H24B 107.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 N1 C1 119.58(18) . . ?
C14 N1 Zn1 123.24(15) . . ?
C1 N1 Zn1 117.15(13) . . ?
C16 N2 C18 117.58(18) . . ?
C16 N2 Zn1 123.18(14) . . ?
C18 N2 Zn1 118.24(13) . . ?
C19 N3 C23 117.52(19) . . ?
C19 N3 Zn1 130.62(15) . . ?
C23 N3 Zn1 111.83(14) . . ?
C24 Zn1 N2 130.62(9) . . ?
C24 Zn1 N1 116.52(9) . . ?
N2 Zn1 N1 94.14(7) . . ?
C24 Zn1 N3 116.20(8) . . ?
N2 Zn1 N3 90.58(7) . . ?
N1 Zn1 N3 103.04(7) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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 1434848'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N3 Zn'
_chemical_formula_sum            'C23 H31 N3 Zn'
_chemical_formula_weight         414.88

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'
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   'P 21/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                   10.6411(6)
_cell_length_b                   14.0394(7)
_cell_length_c                   14.2237(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.421(2)
_cell_angle_gamma                90.00
_cell_volume                     2107.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    1.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8160
_exptl_absorpt_correction_T_max  0.9117
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11629
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.11
_reflns_number_total             3726
_reflns_number_gt                3044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0519P)²+1.7309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3726
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.8194(3) 0.1679(2) 0.6837(2) 0.0249(6) Uani 1 1 d . . .
C2 C 0.7273(3) 0.2337(2) 0.7022(2) 0.0276(6) Uani 1 1 d . . .
C3 C 0.7423(3) 0.2911(2) 0.7921(2) 0.0365(8) Uani 1 1 d . . .
H3A H 0.8240 0.2762 0.8293 0.055 Uiso 1 1 calc R . .
H3B H 0.6735 0.2755 0.8292 0.055 Uiso 1 1 calc R . .
H3C H 0.7390 0.3591 0.7765 0.055 Uiso 1 1 calc R . .
C4 C 0.6173(3) 0.2426(2) 0.6381(2) 0.0334(7) Uani 1 1 d . . .
H4 H 0.5559 0.2886 0.6501 0.040 Uiso 1 1 calc R . .
C5 C 0.5947(3) 0.1869(3) 0.5578(2) 0.0380(8) Uani 1 1 d . . .
C6 C 0.4754(3) 0.1977(3) 0.4891(3) 0.0541(10) Uani 1 1 d . . .
H6A H 0.4765 0.1522 0.4370 0.081 Uiso 1 1 calc R . .
H6B H 0.4705 0.2627 0.4637 0.081 Uiso 1 1 calc R . .
H6C H 0.4016 0.1853 0.5219 0.081 Uiso 1 1 calc R . .
C7 C 0.6844(3) 0.1199(3) 0.5430(2) 0.0380(8) Uani 1 1 d . . .
H7 H 0.6688 0.0793 0.4893 0.046 Uiso 1 1 calc R . .
C8 C 0.7968(3) 0.1093(2) 0.6033(2) 0.0308(7) Uani 1 1 d . . .
C9 C 0.8913(3) 0.0354(2) 0.5826(3) 0.0435(9) Uani 1 1 d . . .
H9A H 0.8593 0.0016 0.5241 0.065 Uiso 1 1 calc R . .
H9B H 0.9044 -0.0101 0.6352 0.065 Uiso 1 1 calc R . .
H9C H 0.9719 0.0663 0.5749 0.065 Uiso 1 1 calc R . .
C10 C 0.8496(3) 0.0377(2) 0.8320(2) 0.0372(8) Uani 1 1 d . . .
H10A H 0.7743 0.0522 0.7871 0.056 Uiso 1 1 calc R . .
H10B H 0.8316 0.0501 0.8968 0.056 Uiso 1 1 calc R . .
H10C H 0.8724 -0.0294 0.8260 0.056 Uiso 1 1 calc R . .
C11 C 0.9585(3) 0.0999(2) 0.8108(2) 0.0283(7) Uani 1 1 d . . .
C12 C 1.0727(3) 0.0869(2) 0.8694(2) 0.0318(7) Uani 1 1 d . . .
H12 H 1.0751 0.0340 0.9113 0.038 Uiso 1 1 calc R . .
C13 C 1.1854(3) 0.1411(2) 0.8754(2) 0.0295(7) Uani 1 1 d . . .
C14 C 1.2870(3) 0.1176(3) 0.9563(2) 0.0426(8) Uani 1 1 d . . .
H14A H 1.3149 0.1641 1.0149 0.051 Uiso 1 1 d R . .
H14B H 1.2430 0.0623 0.9891 0.051 Uiso 1 1 d R . .
H14C H 1.3829 0.1102 0.9362 0.051 Uiso 1 1 d R . .
C15 C 1.3187(3) 0.2680(2) 0.8361(2) 0.0337(7) Uani 1 1 d . . .
H15A H 1.3945 0.2282 0.8320 0.040 Uiso 1 1 calc R . .
H15B H 1.3240 0.2934 0.9014 0.040 Uiso 1 1 calc R . .
C16 C 1.3164(3) 0.3504(2) 0.7660(2) 0.0331(7) Uani 1 1 d . . .
H16A H 1.3969 0.3862 0.7792 0.040 Uiso 1 1 calc R . .
H16B H 1.3119 0.3241 0.7011 0.040 Uiso 1 1 calc R . .
C17 C 1.2079(3) 0.4183(2) 0.7693(2) 0.0283(7) Uani 1 1 d . . .
C18 C 1.2253(3) 0.5097(2) 0.8048(2) 0.0310(7) Uani 1 1 d . . .
H18 H 1.3077 0.5315 0.8289 0.037 Uiso 1 1 calc R . .
C19 C 1.1221(3) 0.5689(2) 0.8051(2) 0.0357(8) Uani 1 1 d . . .
H19 H 1.1325 0.6313 0.8307 0.043 Uiso 1 1 calc R . .
C20 C 1.0044(3) 0.5370(2) 0.7679(2) 0.0375(8) Uani 1 1 d . . .
H20 H 0.9321 0.5769 0.7664 0.045 Uiso 1 1 calc R . .
C21 C 0.9937(3) 0.4455(2) 0.7329(2) 0.0335(7) Uani 1 1 d . . .
H21 H 0.9125 0.4235 0.7058 0.040 Uiso 1 1 calc R . .
C22 C 1.1047(3) 0.2381(2) 0.5583(2) 0.0344(7) Uani 1 1 d . . .
H22A H 1.1713 0.1917 0.5472 0.041 Uiso 1 1 calc R . .
H22B H 1.0243 0.2161 0.5219 0.041 Uiso 1 1 calc R . .
C23 C 1.1389(3) 0.3345(3) 0.5191(3) 0.0453(9) Uani 1 1 d . . .
H23A H 1.1473 0.3281 0.4516 0.068 Uiso 1 1 calc R . .
H23B H 1.2194 0.3566 0.5535 0.068 Uiso 1 1 calc R . .
H23C H 1.0720 0.3806 0.5271 0.068 Uiso 1 1 calc R . .
N1 N 0.9396(2) 0.16351(17) 0.74145(17) 0.0256(5) Uani 1 1 d . . .
N2 N 1.2041(2) 0.20947(18) 0.81553(18) 0.0283(6) Uani 1 1 d . . .
N3 N 1.0924(2) 0.38619(17) 0.73532(18) 0.0292(6) Uani 1 1 d . . .
Zn1 Zn 1.08485(3) 0.23634(2) 0.69640(2) 0.02581(13) 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 1.396(4) . ?
C1 C8 1.403(4) . ?
C1 N1 1.429(3) . ?
C2 C4 1.393(4) . ?
C2 C3 1.503(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.375(5) . ?
C5 C6 1.506(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.501(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.326(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.413(4) . ?
C12 H12 0.9500 . ?
C13 N2 1.315(4) . ?
C13 C14 1.510(4) . ?
C14 H14A 1.0704 . ?
C14 H14B 1.0476 . ?
C14 H14C 1.0991 . ?
C15 N2 1.468(4) . ?
C15 C16 1.525(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.503(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.340(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.377(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(4) . ?
C20 H20 0.9500 . ?
C21 N3 1.337(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.525(5) . ?
C22 Zn1 2.003(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 Zn1 2.025(2) . ?
N2 Zn1 2.017(2) . ?
N3 Zn1 2.174(2) . ?

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 C8 119.4(3) . . ?
C2 C1 N1 121.2(3) . . ?
C8 C1 N1 119.3(3) . . ?
C4 C2 C1 119.1(3) . . ?
C4 C2 C3 119.7(3) . . ?
C1 C2 C3 121.1(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 122.2(3) . . ?
C5 C4 H4 118.9 . . ?
C2 C4 H4 118.9 . . ?
C7 C5 C4 117.6(3) . . ?
C7 C5 C6 120.9(3) . . ?
C4 C5 C6 121.5(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C8 122.6(3) . . ?
C5 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C1 119.0(3) . . ?
C7 C8 C9 119.9(3) . . ?
C1 C8 C9 121.1(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 124.7(3) . . ?
N1 C11 C10 119.4(3) . . ?
C12 C11 C10 115.8(3) . . ?
C11 C12 C13 129.3(3) . . ?
C11 C12 H12 115.4 . . ?
C13 C12 H12 115.4 . . ?
N2 C13 C12 123.5(3) . . ?
N2 C13 C14 119.9(3) . . ?
C12 C13 C14 116.6(3) . . ?
C13 C14 H14A 124.0 . . ?
C13 C14 H14B 100.6 . . ?
H14A C14 H14B 101.5 . . ?
C13 C14 H14C 114.9 . . ?
H14A C14 H14C 95.0 . . ?
H14B C14 H14C 121.9 . . ?
N2 C15 C16 110.6(2) . . ?
N2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 114.1(3) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
N3 C17 C18 121.1(3) . . ?
N3 C17 C16 116.7(3) . . ?
C18 C17 C16 122.2(3) . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 118.3(3) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
N3 C21 C20 122.9(3) . . ?
N3 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C23 C22 Zn1 115.4(2) . . ?
C23 C22 H22A 108.4 . . ?
Zn1 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
Zn1 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 N1 C1 119.7(2) . . ?
C11 N1 Zn1 121.74(19) . . ?
C1 N1 Zn1 117.31(18) . . ?
C13 N2 C15 118.1(3) . . ?
C13 N2 Zn1 123.3(2) . . ?
C15 N2 Zn1 118.6(2) . . ?
C21 N3 C17 118.8(3) . . ?
C21 N3 Zn1 126.4(2) . . ?
C17 N3 Zn1 114.78(19) . . ?
C22 Zn1 N2 133.76(12) . . ?
C22 Zn1 N1 119.85(12) . . ?
N2 Zn1 N1 93.61(10) . . ?
C22 Zn1 N3 103.47(12) . . ?
N2 Zn1 N3 88.20(10) . . ?
N1 Zn1 N3 114.36(9) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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 1434849'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H58 N6 Zn2'
_chemical_formula_sum            'C44 H58 N6 Zn2'
_chemical_formula_weight         801.70

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.137(9)
_cell_length_b                   9.251(10)
_cell_length_c                   14.151(15)
_cell_angle_alpha                79.83(2)
_cell_angle_beta                 78.73(2)
_cell_angle_gamma                76.91(2)
_cell_volume                     1007.6(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7653
_exptl_absorpt_correction_T_max  0.9299
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6025
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.1374
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.15
_reflns_number_total             3483
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1366P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3483
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2035
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.4856(10) 0.3336(9) 0.8992(6) 0.049(2) Uani 1 1 d . . .
H1A H 0.3996 0.4040 0.8638 0.059 Uiso 1 1 calc R . .
H1B H 0.4315 0.3151 0.9681 0.059 Uiso 1 1 calc R . .
C2 C 0.6369(11) 0.4105(10) 0.8947(6) 0.055(2) Uani 1 1 d . . .
H2A H 0.5954 0.5043 0.9228 0.083 Uiso 1 1 calc R . .
H2B H 0.6901 0.4323 0.8268 0.083 Uiso 1 1 calc R . .
H2C H 0.7213 0.3440 0.9317 0.083 Uiso 1 1 calc R . .
C3 C 0.7407(9) 0.2706(8) 0.6674(5) 0.0389(18) Uani 1 1 d . . .
C4 C 0.9156(9) 0.2524(9) 0.6753(6) 0.045(2) Uani 1 1 d . . .
C5 C 1.0194(9) 0.1013(9) 0.7079(6) 0.051(2) Uani 1 1 d . . .
H5A H 1.1365 0.1110 0.7088 0.076 Uiso 1 1 calc R . .
H5B H 1.0212 0.0317 0.6628 0.076 Uiso 1 1 calc R . .
H5C H 0.9678 0.0629 0.7734 0.076 Uiso 1 1 calc R . .
C6 C 0.9882(10) 0.3819(9) 0.6533(6) 0.047(2) Uani 1 1 d . . .
H6 H 1.1045 0.3719 0.6598 0.057 Uiso 1 1 calc R . .
C7 C 0.8992(10) 0.5206(10) 0.6232(6) 0.048(2) Uani 1 1 d . . .
C8 C 0.9800(11) 0.6566(10) 0.6010(7) 0.064(3) Uani 1 1 d . . .
H8A H 0.8960 0.7450 0.5806 0.095 Uiso 1 1 calc R . .
H8B H 1.0781 0.6419 0.5486 0.095 Uiso 1 1 calc R . .
H8C H 1.0186 0.6715 0.6594 0.095 Uiso 1 1 calc R . .
C9 C 0.7290(9) 0.5342(9) 0.6122(6) 0.0431(19) Uani 1 1 d . . .
H9 H 0.6657 0.6291 0.5891 0.052 Uiso 1 1 calc R . .
C10 C 0.6511(9) 0.4101(9) 0.6349(6) 0.045(2) Uani 1 1 d . . .
C11 C 0.4619(10) 0.4292(10) 0.6290(6) 0.052(2) Uani 1 1 d . . .
H11A H 0.4279 0.3316 0.6468 0.077 Uiso 1 1 calc R . .
H11B H 0.4426 0.4704 0.5624 0.077 Uiso 1 1 calc R . .
H11C H 0.3936 0.4979 0.6739 0.077 Uiso 1 1 calc R . .
C12 C 0.7154(10) 0.0834(10) 0.5386(6) 0.052(2) Uani 1 1 d . . .
H12A H 0.7781 0.1654 0.5273 0.078 Uiso 1 1 calc R . .
H12B H 0.6271 0.1078 0.4969 0.078 Uiso 1 1 calc R . .
H12C H 0.7949 -0.0092 0.5232 0.078 Uiso 1 1 calc R . .
C13 C 0.6330(9) 0.0625(8) 0.6432(6) 0.0403(19) Uani 1 1 d . . .
C14 C 0.5358(9) -0.0499(9) 0.6742(6) 0.043(2) Uani 1 1 d . . .
H14 H 0.5417 -0.1130 0.6270 0.052 Uiso 1 1 calc R . .
C15 C 0.4314(9) -0.0847(8) 0.7634(6) 0.0395(18) Uani 1 1 d . . .
C16 C 0.3478(10) -0.2176(9) 0.7695(6) 0.052(2) Uani 1 1 d . . .
H16A H 0.2778 -0.2332 0.8338 0.078 Uiso 1 1 calc R . .
H16B H 0.4364 -0.3074 0.7596 0.078 Uiso 1 1 calc R . .
H16C H 0.2752 -0.1979 0.7191 0.078 Uiso 1 1 calc R . .
C17 C 0.7971(10) -0.1565(10) 0.8664(6) 0.049(2) Uani 1 1 d . . .
H17 H 0.7634 -0.1468 0.8046 0.058 Uiso 1 1 calc R . .
C18 C 0.9106(10) -0.2838(9) 0.8956(6) 0.047(2) Uani 1 1 d . . .
H18 H 0.9545 -0.3598 0.8549 0.057 Uiso 1 1 calc R . .
C19 C 0.9587(10) -0.2982(10) 0.9853(7) 0.053(2) Uani 1 1 d . . .
H19 H 1.0391 -0.3831 1.0072 0.063 Uiso 1 1 calc R . .
C20 C 0.8881(10) -0.1876(9) 1.0420(6) 0.049(2) Uani 1 1 d . . .
H20 H 0.9161 -0.1973 1.1053 0.059 Uiso 1 1 calc R . .
C21 C 0.7765(9) -0.0617(9) 1.0081(6) 0.0409(19) Uani 1 1 d . . .
C22 C 0.7015(10) 0.0613(9) 1.0711(6) 0.047(2) Uani 1 1 d . . .
H22A H 0.7957 0.0986 1.0876 0.056 Uiso 1 1 calc R . .
H22B H 0.6321 0.1458 1.0337 0.056 Uiso 1 1 calc R . .
N1 N 0.6553(7) 0.1478(7) 0.7051(4) 0.0374(15) Uani 1 1 d . . .
N2 N 0.4064(7) -0.0105(7) 0.8383(4) 0.0404(15) Uani 1 1 d . . .
N3 N 0.7315(8) -0.0454(7) 0.9206(5) 0.0416(16) Uani 1 1 d . . .
Zn1 Zn 0.54210(11) 0.14266(10) 0.84516(7) 0.0445(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 1.541(10) . ?
C1 Zn1 1.972(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C10 1.379(11) . ?
C3 C4 1.420(10) . ?
C3 N1 1.434(9) . ?
C4 C6 1.414(11) . ?
C4 C5 1.507(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.363(11) . ?
C6 H6 0.9500 . ?
C7 C9 1.398(11) . ?
C7 C8 1.507(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.393(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.527(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.499(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.339(9) . ?
C13 C14 1.406(10) . ?
C14 C15 1.407(10) . ?
C14 H14 0.9500 . ?
C15 N2 1.322(9) . ?
C15 C16 1.516(10) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.342(10) . ?
C17 C18 1.377(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.366(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(11) . ?
C20 H20 0.9500 . ?
C21 N3 1.332(10) . ?
C21 C22 1.514(10) . ?
C22 N2 1.472(9) 2_657 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N1 Zn1 2.012(6) . ?
N2 C22 1.472(9) 2_657 ?
N2 Zn1 2.009(6) . ?
N3 Zn1 2.305(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
C2 C1 Zn1 115.9(5) . . ?
C2 C1 H1A 108.3 . . ?
Zn1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
Zn1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C10 C3 C4 119.6(7) . . ?
C10 C3 N1 121.1(6) . . ?
C4 C3 N1 118.9(7) . . ?
C6 C4 C3 117.5(7) . . ?
C6 C4 C5 121.2(7) . . ?
C3 C4 C5 121.3(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 123.0(7) . . ?
C7 C6 H6 118.5 . . ?
C4 C6 H6 118.5 . . ?
C6 C7 C9 118.2(7) . . ?
C6 C7 C8 121.7(7) . . ?
C9 C7 C8 120.1(8) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 120.7(8) . . ?
C10 C9 H9 119.6 . . ?
C7 C9 H9 119.6 . . ?
C3 C10 C9 120.8(7) . . ?
C3 C10 C11 119.1(7) . . ?
C9 C10 C11 119.9(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 121.5(7) . . ?
N1 C13 C12 120.2(6) . . ?
C14 C13 C12 118.3(6) . . ?
C13 C14 C15 130.9(7) . . ?
C13 C14 H14 114.6 . . ?
C15 C14 H14 114.6 . . ?
N2 C15 C14 124.0(7) . . ?
N2 C15 C16 120.8(7) . . ?
C14 C15 C16 115.2(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 123.5(8) . . ?
N3 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C19 C18 C17 118.2(8) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C20 C19 C18 118.5(8) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 120.4(8) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
N3 C21 C20 121.5(7) . . ?
N3 C21 C22 118.6(7) . . ?
C20 C21 C22 119.9(7) . . ?
N2 C22 C21 112.7(6) 2_657 . ?
N2 C22 H22A 109.1 2_657 . ?
C21 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 2_657 . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C13 N1 C3 118.8(6) . . ?
C13 N1 Zn1 125.0(5) . . ?
C3 N1 Zn1 115.2(4) . . ?
C15 N2 C22 118.7(6) . 2_657 ?
C15 N2 Zn1 123.3(5) . . ?
C22 N2 Zn1 116.9(5) 2_657 . ?
C21 N3 C17 117.8(7) . . ?
C21 N3 Zn1 130.5(5) . . ?
C17 N3 Zn1 111.7(5) . . ?
C1 Zn1 N2 133.8(3) . . ?
C1 Zn1 N1 116.8(3) . . ?
N2 Zn1 N1 94.2(2) . . ?
C1 Zn1 N3 115.2(3) . . ?
N2 Zn1 N3 88.8(2) . . ?
N1 Zn1 N3 101.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         1.185
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_L3H
_database_code_depnum_ccdc_archive 'CCDC 1434850'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N3'
_chemical_formula_sum            'C23 H31 N3'
_chemical_formula_weight         349.51

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3914(8)
_cell_length_b                   10.7363(10)
_cell_length_c                   11.2888(9)
_cell_angle_alpha                99.922(4)
_cell_angle_beta                 100.271(4)
_cell_angle_gamma                101.376(5)
_cell_volume                     1072.30(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7157
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3667
_reflns_number_gt                2958
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1049P)²+1.9320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    fixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2630
_refine_ls_wR_factor_gt          0.2536
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.2330(4) 0.1825(4) 0.8837(4) 0.0492(10) Uani 1 1 d . . .
H1 H 0.2683 0.2007 0.9705 0.059 Uiso 1 1 calc R . .
C2 C 0.2219(5) 0.0599(4) 0.8185(4) 0.0592(12) Uani 1 1 d . . .
H2 H 0.2475 -0.0056 0.8593 0.071 Uiso 1 1 calc R . .
C3 C 0.1726(6) 0.0334(4) 0.6920(4) 0.0680(14) Uani 1 1 d . . .
H3 H 0.1649 -0.0503 0.6437 0.082 Uiso 1 1 calc R . .
C4 C 0.1348(5) 0.1312(4) 0.6373(4) 0.0526(11) Uani 1 1 d . . .
H4 H 0.0994 0.1153 0.5505 0.063 Uiso 1 1 calc R . .
C5 C 0.1489(4) 0.2516(3) 0.7092(3) 0.0340(8) Uani 1 1 d . . .
C6 C 0.1143(5) 0.3662(4) 0.6587(3) 0.0436(9) Uani 1 1 d . . .
H6A H 0.0253 0.3869 0.6856 0.052 Uiso 1 1 calc R . .
H6B H 0.1986 0.4426 0.6946 0.052 Uiso 1 1 calc R . .
C7 C -0.1816(4) 0.3323(4) 0.4975(4) 0.0485(10) Uani 1 1 d . . .
H7A H -0.1554 0.3441 0.5874 0.073 Uiso 1 1 calc R . .
H7B H -0.2550 0.2496 0.4622 0.073 Uiso 1 1 calc R . .
H7C H -0.2238 0.4040 0.4760 0.073 Uiso 1 1 calc R . .
C8 C -0.0442(4) 0.3308(3) 0.4466(3) 0.0332(8) Uani 1 1 d . . .
C9 C -0.0544(4) 0.3152(3) 0.3224(3) 0.0330(7) Uani 1 1 d . . .
H9 H -0.1497 0.3092 0.2730 0.040 Uiso 1 1 calc R . .
C10 C 0.0637(4) 0.3069(3) 0.2591(3) 0.0307(7) Uani 1 1 d . . .
C11 C 0.0224(4) 0.2840(5) 0.1198(3) 0.0522(10) Uani 1 1 d . . .
H11A H 0.1114 0.2804 0.0865 0.078 Uiso 1 1 calc R . .
H11B H -0.0189 0.3553 0.0959 0.078 Uiso 1 1 calc R . .
H11C H -0.0520 0.2015 0.0868 0.078 Uiso 1 1 calc R . .
C12 C 0.3139(3) 0.3027(3) 0.2555(3) 0.0301(7) Uani 1 1 d . . .
C13 C 0.3542(4) 0.1826(3) 0.2368(3) 0.0355(8) Uani 1 1 d . . .
C14 C 0.2672(5) 0.0660(4) 0.2754(4) 0.0458(9) Uani 1 1 d . . .
H14 H 0.1858 0.0942 0.3114 0.055 Uiso 1 1 calc R . .
C15 C 0.1954(6) -0.0471(5) 0.1664(5) 0.0797(16) Uani 1 1 d . . .
H15A H 0.1402 -0.1194 0.1949 0.119 Uiso 1 1 calc R . .
H15B H 0.2728 -0.0756 0.1283 0.119 Uiso 1 1 calc R . .
H15C H 0.1269 -0.0194 0.1057 0.119 Uiso 1 1 calc R . .
C16 C 0.3662(7) 0.0230(6) 0.3741(5) 0.093(2) Uani 1 1 d . . .
H16A H 0.3078 -0.0508 0.3984 0.140 Uiso 1 1 calc R . .
H16B H 0.4063 0.0951 0.4460 0.140 Uiso 1 1 calc R . .
H16C H 0.4484 -0.0033 0.3417 0.140 Uiso 1 1 calc R . .
C17 C 0.4720(4) 0.1704(4) 0.1800(3) 0.0443(9) Uani 1 1 d . . .
H17 H 0.4993 0.0894 0.1665 0.053 Uiso 1 1 calc R . .
C18 C 0.5501(4) 0.2751(4) 0.1427(3) 0.0453(9) Uani 1 1 d . . .
H18 H 0.6301 0.2656 0.1036 0.054 Uiso 1 1 calc R . .
C19 C 0.5114(4) 0.3924(4) 0.1626(3) 0.0423(9) Uani 1 1 d . . .
H19 H 0.5660 0.4636 0.1372 0.051 Uiso 1 1 calc R . .
C20 C 0.3945(4) 0.4101(3) 0.2187(3) 0.0363(8) Uani 1 1 d . . .
C21 C 0.3563(5) 0.5417(4) 0.2418(4) 0.0476(10) Uani 1 1 d . . .
H21 H 0.2563 0.5286 0.2631 0.057 Uiso 1 1 calc R . .
C22 C 0.4690(6) 0.6338(5) 0.3529(5) 0.0785(17) Uani 1 1 d . . .
H22A H 0.4431 0.7183 0.3673 0.118 Uiso 1 1 calc R . .
H22B H 0.5691 0.6452 0.3362 0.118 Uiso 1 1 calc R . .
H22C H 0.4667 0.5965 0.4261 0.118 Uiso 1 1 calc R . .
C23 C 0.3462(8) 0.6011(6) 0.1282(6) 0.0897(19) Uani 1 1 d . . .
H23A H 0.3209 0.6855 0.1472 0.134 Uiso 1 1 calc R . .
H23B H 0.2690 0.5428 0.0604 0.134 Uiso 1 1 calc R . .
H23C H 0.4423 0.6131 0.1039 0.134 Uiso 1 1 calc R . .
N1 N 0.1970(3) 0.2782(3) 0.8321(3) 0.0429(8) Uani 1 1 d . . .
N2 N 0.0871(3) 0.3452(3) 0.5254(3) 0.0393(7) Uani 1 1 d . . .
H2A H 0.1646 0.3414 0.4923 0.047 Uiso 1 1 calc R . .
N3 N 0.1991(3) 0.3173(3) 0.3194(2) 0.0306(6) 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 1.335(5) . ?
C1 C2 1.368(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(4) . ?
C5 C6 1.510(5) . ?
C6 N2 1.451(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.350(4) . ?
C8 C9 1.367(5) . ?
C9 C10 1.431(5) . ?
C9 H9 0.9500 . ?
C10 N3 1.305(4) . ?
C10 C11 1.515(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.406(5) . ?
C12 C20 1.417(5) . ?
C12 N3 1.418(4) . ?
C13 C17 1.390(5) . ?
C13 C14 1.529(5) . ?
C14 C16 1.516(6) . ?
C14 C15 1.520(6) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.516(5) . ?
C21 C23 1.524(6) . ?
C21 C22 1.535(6) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N2 H2A 0.8800 . ?

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 123.7(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 C6 113.8(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C5 114.1(3) . . ?
N2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 121.4(3) . . ?
N2 C8 C7 118.9(3) . . ?
C9 C8 C7 119.7(3) . . ?
C8 C9 C10 126.7(3) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
N3 C10 C9 121.1(3) . . ?
N3 C10 C11 122.4(3) . . ?
C9 C10 C11 116.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C20 120.1(3) . . ?
C13 C12 N3 119.2(3) . . ?
C20 C12 N3 120.5(3) . . ?
C17 C13 C12 119.2(3) . . ?
C17 C13 C14 120.4(3) . . ?
C12 C13 C14 120.4(3) . . ?
C16 C14 C15 110.3(4) . . ?
C16 C14 C13 110.9(4) . . ?
C15 C14 C13 112.1(3) . . ?
C16 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C13 C17 H17 119.6 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 121.9(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C12 118.3(3) . . ?
C19 C20 C21 120.7(3) . . ?
C12 C20 C21 121.0(3) . . ?
C20 C21 C23 112.3(3) . . ?
C20 C21 C22 110.1(4) . . ?
C23 C21 C22 111.3(4) . . ?
C20 C21 H21 107.6 . . ?
C23 C21 H21 107.6 . . ?
C22 C21 H21 107.6 . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C5 117.4(3) . . ?
C8 N2 C6 127.0(3) . . ?
C8 N2 H2A 116.5 . . ?
C6 N2 H2A 116.5 . . ?
C10 N3 C12 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.061

