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

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

data_1-Zn
_database_code_depnum_ccdc_archive 'CCDC 1046687'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H66 N2 O2 Zn2'
_chemical_formula_sum            'C40 H66 N2 O2 Zn2'
_chemical_formula_weight         737.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.827(6)
_cell_length_b                   12.689(2)
_cell_length_c                   20.032(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.81(3)
_cell_angle_gamma                90
_cell_volume                     3785(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10289
_cell_measurement_theta_min      2.3408
_cell_measurement_theta_max      77.0469

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.815
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, CCD Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_reflns_number            12072
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.578
_diffrn_reflns_theta_max         87.671
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3904
_reflns_number_gt                3692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.1, CCDC 2012'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0927P)²+7.1314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3904
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.98891(2) 0.56077(2) 0.55900(2) 0.01516(14) Uani 1 1 d . . . . .
O1 O 1.07689(11) 0.45245(12) 0.54965(8) 0.0144(3) Uani 1 1 d . . . . .
N1 N 0.90710(13) 0.44589(13) 0.58333(10) 0.0129(4) Uani 1 1 d . . . . .
C1 C 1.10034(14) 0.36660(16) 0.59213(11) 0.0137(4) Uani 1 1 d . . . . .
C2 C 1.03249(15) 0.31034(16) 0.60456(11) 0.0150(4) Uani 1 1 d . . . . .
C3 C 1.06055(15) 0.22458(17) 0.65138(12) 0.0171(4) Uani 1 1 d . . . . .
H3 H 1.0152 0.1852 0.6614 0.020 Uiso 1 1 calc R U . . .
C4 C 1.15326(15) 0.19085(16) 0.68592(11) 0.0155(4) Uani 1 1 d . . . . .
C5 C 1.21926(15) 0.24690(17) 0.67198(11) 0.0163(4) Uani 1 1 d . . . . .
H5 H 1.2807 0.2279 0.6929 0.020 Uiso 1 1 calc R U . . .
C6 C 1.19337(15) 0.33316(17) 0.62596(11) 0.0156(4) Uani 1 1 d . . . . .
H6 H 1.2390 0.3722 0.6162 0.019 Uiso 1 1 calc R U . . .
C11 C 0.93084(15) 0.33877(16) 0.56566(12) 0.0164(4) Uani 1 1 d . . . . .
H11A H 0.9174 0.3340 0.5138 0.020 Uiso 1 1 calc R U . . .
H11B H 0.8929 0.2864 0.5788 0.020 Uiso 1 1 calc R U . . .
C12 C 0.93356(16) 0.45258(18) 0.66024(12) 0.0171(4) Uani 1 1 d . . . . .
H12A H 0.9986 0.4423 0.6814 0.026 Uiso 1 1 calc R U . . .
H12B H 0.9024 0.3979 0.6775 0.026 Uiso 1 1 calc R U . . .
H12C H 0.9175 0.5221 0.6736 0.026 Uiso 1 1 calc R U . . .
C13 C 0.80467(14) 0.46805(17) 0.53815(11) 0.0136(4) Uani 1 1 d . . . . .
H13 H 0.7986 0.4550 0.4875 0.016 Uiso 1 1 calc R U . . .
C14 C 0.78166(15) 0.58386(18) 0.54255(12) 0.0180(4) Uani 1 1 d . . . . .
H14A H 0.8242 0.6282 0.5283 0.022 Uiso 1 1 calc R U . . .
H14B H 0.7881 0.6017 0.5922 0.022 Uiso 1 1 calc R U . . .
C15 C 0.68004(15) 0.60890(18) 0.49143(13) 0.0209(5) Uani 1 1 d . . . . .
H15A H 0.6655 0.6830 0.4986 0.025 Uiso 1 1 calc R U . . .
H15B H 0.6765 0.6012 0.4414 0.025 Uiso 1 1 calc R U . . .
C16 C 0.61161(16) 0.53824(18) 0.50473(13) 0.0198(4) Uani 1 1 d . . . . .
H16A H 0.5519 0.5526 0.4689 0.024 Uiso 1 1 calc R U . . .
H16B H 0.6081 0.5537 0.5522 0.024 Uiso 1 1 calc R U . . .
C17 C 0.63524(15) 0.42242(18) 0.50106(13) 0.0199(5) Uani 1 1 d . . . . .
H17A H 0.6297 0.4043 0.4517 0.024 Uiso 1 1 calc R U . . .
H17B H 0.5924 0.3781 0.5148 0.024 Uiso 1 1 calc R U . . .
C18 C 0.73655(15) 0.39768(17) 0.55324(12) 0.0181(4) Uani 1 1 d . . . . .
H18A H 0.7399 0.4076 0.6031 0.022 Uiso 1 1 calc R U . . .
H18B H 0.7512 0.3232 0.5474 0.022 Uiso 1 1 calc R U . . .
C7 C 1.18045(16) 0.09845(18) 0.73847(12) 0.0197(5) Uani 1 1 d . . . . .
C8 C 1.1817(2) 0.1375(2) 0.80837(14) 0.0325(6) Uani 1 1 d . . . . .
H8A H 1.1225 0.1659 0.8040 0.049 Uiso 1 1 calc R U . . .
H8B H 1.2270 0.1931 0.8248 0.049 Uiso 1 1 calc R U . . .
H8C H 1.1965 0.0793 0.8426 0.049 Uiso 1 1 calc R U . . .
C9 C 1.11022(19) 0.0074(2) 0.70960(15) 0.0312(6) Uani 1 1 d . . . . .
H9A H 1.0501 0.0330 0.7052 0.047 Uiso 1 1 calc R U . . .
H9B H 1.1260 -0.0523 0.7426 0.047 Uiso 1 1 calc R U . . .
H9C H 1.1108 -0.0153 0.6630 0.047 Uiso 1 1 calc R U . . .
C10 C 1.27719(19) 0.05453(19) 0.75274(15) 0.0262(5) Uani 1 1 d . . . . .
H10A H 1.2865 -0.0079 0.7832 0.039 Uiso 1 1 calc R U . . .
H10B H 1.3214 0.1087 0.7763 0.039 Uiso 1 1 calc R U . . .
H10C H 1.2844 0.0352 0.7076 0.039 Uiso 1 1 calc R U . . .
C21 C 1.02382(16) 0.70423(17) 0.60007(12) 0.0203(4) Uani 1 1 d . . . . .
H21A H 1.0901 0.7092 0.6159 0.024 Uiso 1 1 calc R U . . .
H21B H 0.9996 0.7562 0.5614 0.024 Uiso 1 1 calc R U . . .
C22 C 0.99566(19) 0.7361(2) 0.65903(14) 0.0277(5) Uani 1 1 d . . . . .
H22A H 1.0264 0.6927 0.7006 0.042 Uiso 1 1 calc R U . . .
H22B H 0.9306 0.7268 0.6460 0.042 Uiso 1 1 calc R U . . .
H22C H 1.0110 0.8104 0.6702 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 C21 1.997(2) . ?
Zn1 O1 2.0099(16) . ?
Zn1 O1 2.0769(18) 5_766 ?
Zn1 N1 2.1134(18) . ?
Zn1 Zn1 2.9412(9) 5_766 ?
O1 C1 1.354(2) . ?
O1 Zn1 2.0769(18) 5_766 ?
N1 C12 1.455(3) . ?
N1 C11 1.485(3) . ?
N1 C13 1.591(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.460(3) . ?
C2 C3 1.407(3) . ?
C2 C11 1.573(3) . ?
C3 C4 1.458(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(3) . ?
C4 C7 1.537(3) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.507(3) . ?
C13 C14 1.524(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.619(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.498(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.620(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C7 C8 1.479(3) . ?
C7 C10 1.562(3) . ?
C7 C9 1.571(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C21 C22 1.454(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C21 Zn1 O1 123.92(9) . . ?
C21 Zn1 O1 118.41(8) . 5_766 ?
O1 Zn1 O1 87.96(7) . 5_766 ?
C21 Zn1 N1 129.74(8) . . ?
O1 Zn1 N1 92.74(7) . . ?
O1 Zn1 N1 93.28(7) 5_766 . ?
C21 Zn1 Zn1 135.83(7) . 5_766 ?
O1 Zn1 Zn1 44.88(5) . 5_766 ?
O1 Zn1 Zn1 43.07(4) 5_766 5_766 ?
N1 Zn1 Zn1 94.19(5) . 5_766 ?
C1 O1 Zn1 122.85(13) . . ?
C1 O1 Zn1 121.79(13) . 5_766 ?
Zn1 O1 Zn1 92.04(7) . 5_766 ?
C12 N1 C11 107.49(17) . . ?
C12 N1 C13 117.64(17) . . ?
C11 N1 C13 108.52(16) . . ?
C12 N1 Zn1 103.00(13) . . ?
C11 N1 Zn1 110.61(13) . . ?
C13 N1 Zn1 109.43(12) . . ?
O1 C1 C2 117.71(19) . . ?
O1 C1 C6 122.96(18) . . ?
C2 C1 C6 119.32(19) . . ?
C1 C2 C3 115.5(2) . . ?
C1 C2 C11 121.28(19) . . ?
C3 C2 C11 123.12(19) . . ?
C2 C3 C4 125.7(2) . . ?
C2 C3 H3 117.2 . . ?
C4 C3 H3 117.2 . . ?
C5 C4 C3 117.75(19) . . ?
C5 C4 C7 118.7(2) . . ?
C3 C4 C7 123.51(19) . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 123.86(19) . . ?
C5 C6 H6 118.1 . . ?
C1 C6 H6 118.1 . . ?
N1 C11 C2 113.00(17) . . ?
N1 C11 H11A 109.0 . . ?
C2 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C2 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 111.02(17) . . ?
C18 C13 N1 116.19(17) . . ?
C14 C13 N1 110.79(17) . . ?
C18 C13 H13 106.0 . . ?
C14 C13 H13 106.0 . . ?
N1 C13 H13 106.0 . . ?
C13 C14 C15 111.00(18) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 113.16(18) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 111.37(18) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.16(19) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C13 C18 C17 111.99(18) . . ?
C13 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C13 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C8 C7 C4 107.70(19) . . ?
C8 C7 C10 104.4(2) . . ?
C4 C7 C10 115.29(18) . . ?
C8 C7 C9 112.1(2) . . ?
C4 C7 C9 108.06(19) . . ?
C10 C7 C9 109.4(2) . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 C21 Zn1 118.05(16) . . ?
C22 C21 H21A 107.8 . . ?
Zn1 C21 H21A 107.8 . . ?
C22 C21 H21B 107.8 . . ?
Zn1 C21 H21B 107.8 . . ?
H21A C21 H21B 107.1 . . ?
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 . . ?

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
Zn1 O1 C1 C2 45.5(2) . . . . ?
Zn1 O1 C1 C2 -71.2(2) 5_766 . . . ?
Zn1 O1 C1 C6 -133.15(17) . . . . ?
Zn1 O1 C1 C6 110.1(2) 5_766 . . . ?
O1 C1 C2 C3 -177.40(18) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
O1 C1 C2 C11 5.2(3) . . . . ?
C6 C1 C2 C11 -176.10(18) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C11 C2 C3 C4 176.44(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C7 178.1(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C7 C4 C5 C6 -177.72(19) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
O1 C1 C6 C5 177.68(19) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C12 N1 C11 C2 -54.7(2) . . . . ?
C13 N1 C11 C2 177.10(16) . . . . ?
Zn1 N1 C11 C2 57.05(19) . . . . ?
C1 C2 C11 N1 -62.9(2) . . . . ?
C3 C2 C11 N1 119.9(2) . . . . ?
C12 N1 C13 C18 -58.6(2) . . . . ?
C11 N1 C13 C18 63.6(2) . . . . ?
Zn1 N1 C13 C18 -175.64(14) . . . . ?
C12 N1 C13 C14 69.3(2) . . . . ?
C11 N1 C13 C14 -168.53(16) . . . . ?
Zn1 N1 C13 C14 -47.74(18) . . . . ?
C18 C13 C14 C15 -54.2(2) . . . . ?
N1 C13 C14 C15 175.18(16) . . . . ?
C13 C14 C15 C16 53.8(2) . . . . ?
C14 C15 C16 C17 -53.5(3) . . . . ?
C15 C16 C17 C18 53.4(3) . . . . ?
C14 C13 C18 C17 55.7(2) . . . . ?
N1 C13 C18 C17 -176.49(16) . . . . ?
C16 C17 C18 C13 -55.3(2) . . . . ?
C5 C4 C7 C8 97.3(3) . . . . ?
C3 C4 C7 C8 -80.7(3) . . . . ?
C5 C4 C7 C10 -18.7(3) . . . . ?
C3 C4 C7 C10 163.3(2) . . . . ?
C5 C4 C7 C9 -141.4(2) . . . . ?
C3 C4 C7 C9 40.5(3) . . . . ?

_refine_diff_density_max         0.687
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.102

_shelxl_version_number           2013-4

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

data_3-Zn
_database_code_depnum_ccdc_archive 'CCDC 1046688'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H54 N2 O2 Zn2'
_chemical_formula_sum            'C40 H54 N2 O2 Zn2'
_chemical_formula_weight         725.59

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   15.727(9)
_cell_length_b                   13.996(7)
_cell_length_c                   15.894(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3498(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4081
_cell_measurement_theta_min      2.9052
_cell_measurement_theta_max      28.6195

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    1.408
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'medium-focus sealed tube'
_diffrn_measurement_device_type  'Kuma KM-4-CCD κ-geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14620
_diffrn_reflns_av_unetI/netI     0.1405
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         28.679
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_point_group_measured_fraction_full 0.799
_reflns_number_total             6636
_reflns_number_gt                3761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.547
_reflns_Friedel_fraction_max     0.538
_reflns_Friedel_fraction_full    0.602

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

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.1, CCDC 2012'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0834P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6636
_refine_ls_number_parameters     419
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.21875(7) 0.49108(7) -0.01712(8) 0.0231(3) Uani 1 1 d . . . . .
Zn2 Zn 0.04350(7) 0.47810(7) 0.07022(7) 0.0228(3) Uani 1 1 d . . . . .
O1 O 0.1023(4) 0.5571(4) -0.0222(5) 0.0238(14) Uani 1 1 d . . . . .
O2 O 0.1575(4) 0.4071(4) 0.0705(5) 0.0222(14) Uani 1 1 d . . . . .
N1 N 0.2713(5) 0.6037(5) 0.0581(5) 0.0231(19) Uani 1 1 d . . . . .
N2 N -0.0205(5) 0.3732(5) -0.0012(5) 0.0228(19) Uani 1 1 d . . . . .
C1 C 0.0983(6) 0.6538(6) -0.0209(7) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.1427(6) 0.7049(6) 0.0393(6) 0.019(2) Uani 1 1 d . . . . .
C3 C 0.1352(6) 0.8046(6) 0.0407(6) 0.026(2) Uani 1 1 d . . . . .
H3 H 0.1654 0.8396 0.0823 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0847(6) 0.8542(6) -0.0170(7) 0.023(2) Uani 1 1 d . . . . .
H4 H 0.0804 0.9219 -0.0141 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0401(6) 0.8032(6) -0.0794(6) 0.021(2) Uani 1 1 d . . . . .
C6 C 0.0474(6) 0.7015(6) -0.0830(6) 0.019(2) Uani 1 1 d . . . . .
C7 C -0.0075(6) 0.8497(7) -0.1413(6) 0.023(2) Uani 1 1 d . . . . .
H7 H -0.0112 0.9175 -0.1406 0.028 Uiso 1 1 calc R U . . .
C8 C -0.0492(6) 0.7997(7) -0.2031(6) 0.026(2) Uani 1 1 d . . . . .
H8 H -0.0849 0.8322 -0.2419 0.032 Uiso 1 1 calc R U . . .
C9 C -0.0389(6) 0.7017(7) -0.2087(6) 0.027(2) Uani 1 1 d . . . . .
H9 H -0.0645 0.6677 -0.2538 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0085(6) 0.6525(7) -0.1490(6) 0.024(2) Uani 1 1 d . . . . .
H10 H 0.0145 0.5851 -0.1532 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1990(6) 0.6553(6) 0.1002(6) 0.023(2) Uani 1 1 d . . . . .
H11A H 0.1649 0.6087 0.1328 0.027 Uiso 1 1 calc R U . . .
H11B H 0.2223 0.7027 0.1403 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3153(7) 0.6681(6) -0.0015(7) 0.029(3) Uani 1 1 d . . . . .
H12A H 0.3663 0.6364 -0.0234 0.043 Uiso 1 1 calc R U . . .
H12B H 0.3318 0.7270 0.0277 0.043 Uiso 1 1 calc R U . . .
H12C H 0.2771 0.6837 -0.0482 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3320(6) 0.5686(6) 0.1240(6) 0.023(2) Uani 1 1 d . . . . .
H13 H 0.2969 0.5400 0.1700 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3895(6) 0.4886(6) 0.0901(7) 0.024(2) Uani 1 1 d . . . . .
H14A H 0.3540 0.4357 0.0683 0.029 Uiso 1 1 calc R U . . .
H14B H 0.4244 0.5135 0.0430 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4477(7) 0.4513(7) 0.1597(7) 0.030(3) Uani 1 1 d . . . . .
H15A H 0.4126 0.4225 0.2048 0.036 Uiso 1 1 calc R U . . .
H15B H 0.4850 0.4008 0.1366 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5024(6) 0.5308(7) 0.1969(7) 0.027(2) Uani 1 1 d . . . . .
H16A H 0.5390 0.5045 0.2420 0.033 Uiso 1 1 calc R U . . .
H16B H 0.5396 0.5578 0.1527 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4458(7) 0.6092(7) 0.2329(7) 0.030(2) Uani 1 1 d . . . . .
H17A H 0.4116 0.5835 0.2800 0.036 Uiso 1 1 calc R U . . .
H17B H 0.4814 0.6620 0.2548 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3880(7) 0.6460(7) 0.1650(7) 0.029(2) Uani 1 1 d . . . . .
H18A H 0.4230 0.6765 0.1207 0.035 Uiso 1 1 calc R U . . .
H18B H 0.3506 0.6958 0.1892 0.035 Uiso 1 1 calc R U . . .
C21 C 0.2881(8) 0.4394(8) -0.1126(7) 0.037(3) Uani 1 1 d . . . . .
H21A H 0.3157 0.4938 -0.1415 0.044 Uiso 1 1 calc R U . . .
H21B H 0.3338 0.3989 -0.0888 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2411(8) 0.3817(8) -0.1774(8) 0.049(3) Uani 1 1 d . . . . .
H22A H 0.2785 0.3694 -0.2255 0.074 Uiso 1 1 calc R U . . .
H22B H 0.1909 0.4172 -0.1963 0.074 Uiso 1 1 calc R U . . .
H22C H 0.2232 0.3208 -0.1526 0.074 Uiso 1 1 calc R U . . .
C31 C 0.1549(6) 0.3114(5) 0.0663(8) 0.023(2) Uani 1 1 d . . . . .
C32 C 0.1047(6) 0.2642(7) 0.0104(6) 0.021(2) Uani 1 1 d . . . . .
C33 C 0.1047(6) 0.1622(6) 0.0092(7) 0.029(3) Uani 1 1 d . . . . .
H33 H 0.0706 0.1305 -0.0314 0.034 Uiso 1 1 calc R U . . .
C34 C 0.1521(5) 0.1076(6) 0.0643(7) 0.024(2) Uani 1 1 d . . . . .
H34 H 0.1519 0.0398 0.0611 0.029 Uiso 1 1 calc R U . . .
C35 C 0.2009(7) 0.1560(6) 0.1256(7) 0.026(2) Uani 1 1 d . . . . .
C36 C 0.2047(6) 0.2572(6) 0.1281(6) 0.020(2) Uani 1 1 d . . . . .
C37 C 0.2461(6) 0.1054(7) 0.1880(7) 0.025(2) Uani 1 1 d . . . . .
H37 H 0.2460 0.0375 0.1869 0.029 Uiso 1 1 calc R U . . .
C38 C 0.2900(7) 0.1515(7) 0.2498(7) 0.033(3) Uani 1 1 d . . . . .
H38 H 0.3183 0.1158 0.2923 0.040 Uiso 1 1 calc R U . . .
C39 C 0.2934(6) 0.2503(7) 0.2507(6) 0.026(2) Uani 1 1 d . . . . .
H39 H 0.3250 0.2817 0.2935 0.031 Uiso 1 1 calc R U . . .
C40 C 0.2519(7) 0.3040(7) 0.1908(7) 0.027(2) Uani 1 1 d . . . . .
H40 H 0.2551 0.3718 0.1919 0.032 Uiso 1 1 calc R U . . .
C41 C 0.0459(7) 0.3184(6) -0.0488(6) 0.025(2) Uani 1 1 d . . . . .
H41A H 0.0799 0.3632 -0.0834 0.030 Uiso 1 1 calc R U . . .
H41B H 0.0178 0.2726 -0.0873 0.030 Uiso 1 1 calc R U . . .
C42 C -0.0657(6) 0.3077(6) 0.0591(7) 0.025(2) Uani 1 1 d . . . . .
H42A H -0.0256 0.2851 0.1018 0.038 Uiso 1 1 calc R U . . .
H42B H -0.0888 0.2529 0.0282 0.038 Uiso 1 1 calc R U . . .
H42C H -0.1123 0.3424 0.0864 0.038 Uiso 1 1 calc R U . . .
C43 C -0.0820(7) 0.4175(6) -0.0635(6) 0.024(2) Uani 1 1 d . . . . .
H43 H -0.0474 0.4447 -0.1105 0.029 Uiso 1 1 calc R U . . .
C44 C -0.1306(6) 0.5002(6) -0.0232(7) 0.024(2) Uani 1 1 d . . . . .
H44A H -0.1660 0.4754 0.0234 0.028 Uiso 1 1 calc R U . . .
H44B H -0.0895 0.5463 0.0009 0.028 Uiso 1 1 calc R U . . .
C45 C -0.1873(7) 0.5516(7) -0.0866(7) 0.032(3) Uani 1 1 d . . . . .
H45A H -0.1514 0.5835 -0.1293 0.039 Uiso 1 1 calc R U . . .
H45B H -0.2208 0.6013 -0.0573 0.039 Uiso 1 1 calc R U . . .
C46 C -0.2482(7) 0.4809(7) -0.1306(7) 0.030(2) Uani 1 1 d . . . . .
H46A H -0.2897 0.4561 -0.0891 0.036 Uiso 1 1 calc R U . . .
H46B H -0.2802 0.5147 -0.1752 0.036 Uiso 1 1 calc R U . . .
C47 C -0.2002(7) 0.3990(7) -0.1686(7) 0.030(2) Uani 1 1 d . . . . .
H47A H -0.1627 0.4231 -0.2139 0.036 Uiso 1 1 calc R U . . .
H47B H -0.2408 0.3532 -0.1938 0.036 Uiso 1 1 calc R U . . .
C48 C -0.1471(7) 0.3485(7) -0.1028(7) 0.030(2) Uani 1 1 d . . . . .
H48A H -0.1168 0.2941 -0.1290 0.036 Uiso 1 1 calc R U . . .
H48B H -0.1847 0.3229 -0.0582 0.036 Uiso 1 1 calc R U . . .
C51 C -0.0049(7) 0.5267(6) 0.1766(7) 0.027(2) Uani 1 1 d . . . . .
H51A H -0.0557 0.4877 0.1897 0.032 Uiso 1 1 calc R U . . .
H51B H 0.0372 0.5143 0.2216 0.032 Uiso 1 1 calc R U . . .
C52 C -0.0300(8) 0.6278(8) 0.1828(8) 0.047(3) Uani 1 1 d . . . . .
H52A H -0.0790 0.6396 0.1462 0.070 Uiso 1 1 calc R U . . .
H52B H 0.0176 0.6684 0.1651 0.070 Uiso 1 1 calc R U . . .
H52C H -0.0451 0.6427 0.2411 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 C21 2.004(12) . ?
Zn1 O1 2.053(6) . ?
Zn1 O2 2.062(7) . ?
Zn1 N1 2.144(8) . ?
Zn1 Zn2 3.091(2) . ?
Zn2 C51 1.975(11) . ?
Zn2 O2 2.049(6) . ?
Zn2 O1 2.058(7) . ?
Zn2 N2 2.111(8) . ?
O1 C1 1.355(9) . ?
O2 C31 1.342(9) . ?
N1 C12 1.479(11) . ?
N1 C13 1.500(12) . ?
N1 C11 1.505(11) . ?
N2 C41 1.501(12) . ?
N2 C42 1.505(12) . ?
N2 C43 1.516(12) . ?
C1 C2 1.384(13) . ?
C1 C6 1.436(13) . ?
C2 C3 1.400(12) . ?
C2 C11 1.484(13) . ?
C3 C4 1.399(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(14) . ?
C4 H4 0.9500 . ?
C5 C7 1.397(13) . ?
C5 C6 1.430(13) . ?
C6 C10 1.394(13) . ?
C7 C8 1.374(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(14) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.537(12) . ?
C13 C18 1.539(13) . ?
C13 H13 1.0000 . ?
C14 C15 1.528(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.525(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.502(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C21 C22 1.503(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 C32 1.360(13) . ?
C31 C36 1.468(14) . ?
C32 C33 1.428(13) . ?
C32 C41 1.521(13) . ?
C33 C34 1.380(13) . ?
C33 H33 0.9500 . ?
C34 C35 1.413(14) . ?
C34 H34 0.9500 . ?
C35 C37 1.411(14) . ?
C35 C36 1.419(12) . ?
C36 C40 1.405(14) . ?
C37 C38 1.364(15) . ?
C37 H37 0.9500 . ?
C38 C39 1.384(13) . ?
C38 H38 0.9500 . ?
C39 C40 1.378(14) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.527(13) . ?
C43 C48 1.540(13) . ?
C43 H43 1.0000 . ?
C44 C45 1.526(14) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.544(15) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.499(14) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.514(14) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C51 C52 1.472(14) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 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
C21 Zn1 O1 128.2(4) . . ?
C21 Zn1 O2 124.1(4) . . ?
O1 Zn1 O2 82.3(2) . . ?
C21 Zn1 N1 118.5(4) . . ?
O1 Zn1 N1 92.0(3) . . ?
O2 Zn1 N1 102.9(3) . . ?
C21 Zn1 Zn2 143.5(3) . . ?
O1 Zn1 Zn2 41.31(19) . . ?
O2 Zn1 Zn2 41.08(16) . . ?
N1 Zn1 Zn2 97.9(2) . . ?
C51 Zn2 O2 120.1(4) . . ?
C51 Zn2 O1 126.8(3) . . ?
O2 Zn2 O1 82.5(3) . . ?
C51 Zn2 N2 121.1(4) . . ?
O2 Zn2 N2 94.7(3) . . ?
O1 Zn2 N2 101.8(3) . . ?
C51 Zn2 Zn1 135.0(3) . . ?
O2 Zn2 Zn1 41.39(19) . . ?
O1 Zn2 Zn1 41.17(17) . . ?
N2 Zn2 Zn1 103.0(2) . . ?
C1 O1 Zn1 119.4(6) . . ?
C1 O1 Zn2 120.3(6) . . ?
Zn1 O1 Zn2 97.5(3) . . ?
C31 O2 Zn2 117.2(5) . . ?
C31 O2 Zn1 123.3(6) . . ?
Zn2 O2 Zn1 97.5(3) . . ?
C12 N1 C13 110.4(7) . . ?
C12 N1 C11 110.3(7) . . ?
C13 N1 C11 109.1(8) . . ?
C12 N1 Zn1 105.8(6) . . ?
C13 N1 Zn1 113.2(5) . . ?
C11 N1 Zn1 108.0(5) . . ?
C41 N2 C42 109.8(7) . . ?
C41 N2 C43 108.9(8) . . ?
C42 N2 C43 111.3(7) . . ?
C41 N2 Zn2 107.2(5) . . ?
C42 N2 Zn2 107.9(6) . . ?
C43 N2 Zn2 111.8(5) . . ?
O1 C1 C2 120.2(9) . . ?
O1 C1 C6 118.6(9) . . ?
C2 C1 C6 121.1(8) . . ?
C1 C2 C3 118.9(8) . . ?
C1 C2 C11 120.7(8) . . ?
C3 C2 C11 120.4(8) . . ?
C4 C3 C2 122.2(9) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.5(8) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C7 C5 C4 121.8(8) . . ?
C7 C5 C6 118.6(8) . . ?
C4 C5 C6 119.6(8) . . ?
C10 C6 C5 119.0(8) . . ?
C10 C6 C1 122.2(8) . . ?
C5 C6 C1 118.7(8) . . ?
C8 C7 C5 121.5(9) . . ?
C8 C7 H7 119.3 . . ?
C5 C7 H7 119.3 . . ?
C7 C8 C9 119.7(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.7(9) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C6 120.3(9) . . ?
C9 C10 H10 119.8 . . ?
C6 C10 H10 119.8 . . ?
C2 C11 N1 112.6(8) . . ?
C2 C11 H11A 109.1 . . ?
N1 C11 H11A 109.1 . . ?
C2 C11 H11B 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 111.5(8) . . ?
N1 C13 C18 115.4(7) . . ?
C14 C13 C18 108.9(8) . . ?
N1 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C18 C13 H13 106.8 . . ?
C15 C14 C13 110.3(8) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 111.6(8) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 109.9(8) . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 109.3(9) . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 C13 114.1(8) . . ?
C17 C18 H18A 108.7 . . ?
C13 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C13 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C22 C21 Zn1 116.4(9) . . ?
C22 C21 H21A 108.2 . . ?
Zn1 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
Zn1 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?
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 . . ?
O2 C31 C32 122.3(10) . . ?
O2 C31 C36 117.8(9) . . ?
C32 C31 C36 119.7(7) . . ?
C31 C32 C33 119.6(8) . . ?
C31 C32 C41 121.0(8) . . ?
C33 C32 C41 119.4(8) . . ?
C34 C33 C32 123.1(9) . . ?
C34 C33 H33 118.5 . . ?
C32 C33 H33 118.5 . . ?
C33 C34 C35 117.7(8) . . ?
C33 C34 H34 121.1 . . ?
C35 C34 H34 121.1 . . ?
C37 C35 C34 121.2(9) . . ?
C37 C35 C36 117.4(9) . . ?
C34 C35 C36 121.4(9) . . ?
C40 C36 C35 120.5(9) . . ?
C40 C36 C31 121.0(8) . . ?
C35 C36 C31 118.4(8) . . ?
C38 C37 C35 121.6(9) . . ?
C38 C37 H37 119.2 . . ?
C35 C37 H37 119.2 . . ?
C37 C38 C39 120.0(10) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C40 C39 C38 121.3(10) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C36 119.1(9) . . ?
C39 C40 H40 120.5 . . ?
C36 C40 H40 120.5 . . ?
N2 C41 C32 111.5(8) . . ?
N2 C41 H41A 109.3 . . ?
C32 C41 H41A 109.3 . . ?
N2 C41 H41B 109.3 . . ?
C32 C41 H41B 109.3 . . ?
H41A C41 H41B 108.0 . . ?
N2 C42 H42A 109.5 . . ?
N2 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N2 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N2 C43 C44 110.8(8) . . ?
N2 C43 C48 115.6(7) . . ?
C44 C43 C48 108.3(8) . . ?
N2 C43 H43 107.3 . . ?
C44 C43 H43 107.3 . . ?
C48 C43 H43 107.3 . . ?
C45 C44 C43 111.9(9) . . ?
C45 C44 H44A 109.2 . . ?
C43 C44 H44A 109.2 . . ?
C45 C44 H44B 109.2 . . ?
C43 C44 H44B 109.2 . . ?
H44A C44 H44B 107.9 . . ?
C44 C45 C46 111.1(8) . . ?
C44 C45 H45A 109.4 . . ?
C46 C45 H45A 109.4 . . ?
C44 C45 H45B 109.4 . . ?
C46 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
C47 C46 C45 111.1(8) . . ?
C47 C46 H46A 109.4 . . ?
C45 C46 H46A 109.4 . . ?
C47 C46 H46B 109.4 . . ?
C45 C46 H46B 109.4 . . ?
H46A C46 H46B 108.0 . . ?
C46 C47 C48 110.9(9) . . ?
C46 C47 H47A 109.5 . . ?
C48 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
C47 C48 C43 110.7(8) . . ?
C47 C48 H48A 109.5 . . ?
C43 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C43 C48 H48B 109.5 . . ?
H48A C48 H48B 108.1 . . ?
C52 C51 Zn2 119.4(8) . . ?
C52 C51 H51A 107.5 . . ?
Zn2 C51 H51A 107.5 . . ?
C52 C51 H51B 107.5 . . ?
Zn2 C51 H51B 107.5 . . ?
H51A C51 H51B 107.0 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 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
Zn1 O1 C1 C2 -49.1(12) . . . . ?
Zn2 O1 C1 C2 71.1(10) . . . . ?
Zn1 O1 C1 C6 130.7(8) . . . . ?
Zn2 O1 C1 C6 -109.1(9) . . . . ?
O1 C1 C2 C3 -178.0(9) . . . . ?
C6 C1 C2 C3 2.2(14) . . . . ?
O1 C1 C2 C11 3.2(14) . . . . ?
C6 C1 C2 C11 -176.5(8) . . . . ?
C1 C2 C3 C4 -0.5(14) . . . . ?
C11 C2 C3 C4 178.3(9) . . . . ?
C2 C3 C4 C5 -0.5(15) . . . . ?
C3 C4 C5 C7 -176.5(9) . . . . ?
C3 C4 C5 C6 -0.2(14) . . . . ?
C7 C5 C6 C10 1.5(14) . . . . ?
C4 C5 C6 C10 -174.9(9) . . . . ?
C7 C5 C6 C1 178.3(9) . . . . ?
C4 C5 C6 C1 1.8(14) . . . . ?
O1 C1 C6 C10 -6.0(14) . . . . ?
C2 C1 C6 C10 173.8(9) . . . . ?
O1 C1 C6 C5 177.4(8) . . . . ?
C2 C1 C6 C5 -2.9(14) . . . . ?
C4 C5 C7 C8 178.4(10) . . . . ?
C6 C5 C7 C8 2.1(14) . . . . ?
C5 C7 C8 C9 -5.0(15) . . . . ?
C7 C8 C9 C10 4.4(15) . . . . ?
C8 C9 C10 C6 -0.8(15) . . . . ?
C5 C6 C10 C9 -2.2(14) . . . . ?
C1 C6 C10 C9 -178.8(9) . . . . ?
C1 C2 C11 N1 62.3(12) . . . . ?
C3 C2 C11 N1 -116.4(9) . . . . ?
C12 N1 C11 C2 49.9(10) . . . . ?
C13 N1 C11 C2 171.4(8) . . . . ?
Zn1 N1 C11 C2 -65.2(8) . . . . ?
C12 N1 C13 C14 -77.8(9) . . . . ?
C11 N1 C13 C14 160.9(8) . . . . ?
Zn1 N1 C13 C14 40.6(9) . . . . ?
C12 N1 C13 C18 47.2(10) . . . . ?
C11 N1 C13 C18 -74.2(10) . . . . ?
Zn1 N1 C13 C18 165.6(7) . . . . ?
N1 C13 C14 C15 -177.4(8) . . . . ?
C18 C13 C14 C15 54.1(11) . . . . ?
C13 C14 C15 C16 -57.9(11) . . . . ?
C14 C15 C16 C17 59.0(11) . . . . ?
C15 C16 C17 C18 -57.0(11) . . . . ?
C16 C17 C18 C13 57.2(12) . . . . ?
N1 C13 C18 C17 177.9(9) . . . . ?
C14 C13 C18 C17 -55.8(12) . . . . ?
Zn2 O2 C31 C32 46.2(13) . . . . ?
Zn1 O2 C31 C32 -74.7(10) . . . . ?
Zn2 O2 C31 C36 -129.9(7) . . . . ?
Zn1 O2 C31 C36 109.1(9) . . . . ?
O2 C31 C32 C33 -179.8(8) . . . . ?
C36 C31 C32 C33 -3.7(14) . . . . ?
O2 C31 C32 C41 -2.1(15) . . . . ?
C36 C31 C32 C41 174.0(8) . . . . ?
C31 C32 C33 C34 1.9(15) . . . . ?
C41 C32 C33 C34 -175.9(9) . . . . ?
C32 C33 C34 C35 1.5(15) . . . . ?
C33 C34 C35 C37 175.4(9) . . . . ?
C33 C34 C35 C36 -3.0(15) . . . . ?
C37 C35 C36 C40 0.0(14) . . . . ?
C34 C35 C36 C40 178.4(10) . . . . ?
C37 C35 C36 C31 -177.2(9) . . . . ?
C34 C35 C36 C31 1.3(14) . . . . ?
O2 C31 C36 C40 1.3(14) . . . . ?
C32 C31 C36 C40 -175.0(10) . . . . ?
O2 C31 C36 C35 178.5(9) . . . . ?
C32 C31 C36 C35 2.2(14) . . . . ?
C34 C35 C37 C38 -176.8(10) . . . . ?
C36 C35 C37 C38 1.7(15) . . . . ?
C35 C37 C38 C39 -2.2(16) . . . . ?
C37 C38 C39 C40 1.1(16) . . . . ?
C38 C39 C40 C36 0.6(16) . . . . ?
C35 C36 C40 C39 -1.1(15) . . . . ?
C31 C36 C40 C39 176.0(9) . . . . ?
C42 N2 C41 C32 -52.4(10) . . . . ?
C43 N2 C41 C32 -174.5(7) . . . . ?
Zn2 N2 C41 C32 64.4(8) . . . . ?
C31 C32 C41 N2 -63.0(12) . . . . ?
C33 C32 C41 N2 114.7(9) . . . . ?
C41 N2 C43 C44 -160.1(7) . . . . ?
C42 N2 C43 C44 78.7(9) . . . . ?
Zn2 N2 C43 C44 -41.9(9) . . . . ?
C41 N2 C43 C48 76.2(10) . . . . ?
C42 N2 C43 C48 -44.9(11) . . . . ?
Zn2 N2 C43 C48 -165.6(7) . . . . ?
N2 C43 C44 C45 175.0(8) . . . . ?
C48 C43 C44 C45 -57.2(10) . . . . ?
C43 C44 C45 C46 54.8(11) . . . . ?
C44 C45 C46 C47 -53.6(12) . . . . ?
C45 C46 C47 C48 56.3(12) . . . . ?
C46 C47 C48 C43 -60.2(11) . . . . ?
N2 C43 C48 C47 -175.6(9) . . . . ?
C44 C43 C48 C47 59.5(11) . . . . ?

_refine_diff_density_max         2.880
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.150

_shelxl_version_number           2013-4

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

data_L1H
_database_code_depnum_ccdc_archive 'CCDC 1046691'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H29 N O'
_chemical_formula_sum            'C18 H29 N O'
_chemical_formula_weight         275.42

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'

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

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

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

_cell_length_a                   6.519(5)
_cell_length_b                   26.13(2)
_cell_length_c                   9.596(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.95(4)
_cell_angle_gamma                90
_cell_volume                     1629(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2160
_cell_measurement_theta_min      3.1119
_cell_measurement_theta_max      28.6765

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            7481
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.118
_diffrn_reflns_theta_max         28.740
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3700
_reflns_number_gt                2818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.5707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.70008(16) 0.08397(4) 0.88881(11) 0.0241(3) Uani 1 1 d . . . . .
H H 0.593(3) 0.0725(8) 0.941(2) 0.053(6) Uiso 1 1 d . . . . .
N N 0.34200(18) 0.07291(4) 0.99215(12) 0.0159(3) Uani 1 1 d . . . . .
C1 C 0.6066(2) 0.11941(5) 0.80023(14) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.4177(2) 0.14105(5) 0.82696(14) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.3275(2) 0.17631(5) 0.73282(14) 0.0148(3) Uani 1 1 d . . . . .
H3 H 0.1977 0.1904 0.7501 0.018 Uiso 1 1 calc R U . . .
C4 C 0.4190(2) 0.19212(5) 0.61366(14) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.6075(2) 0.16990(6) 0.59095(15) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.6743 0.1796 0.5109 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7000(2) 0.13397(6) 0.68214(15) 0.0217(3) Uani 1 1 d . . . . .
H6 H 0.8281 0.1193 0.6636 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3180(2) 0.12762(5) 0.95926(14) 0.0166(3) Uani 1 1 d . . . . .
H11A H 0.3819 0.1481 1.0382 0.020 Uiso 1 1 calc R U . . .
H11B H 0.1697 0.1363 0.9470 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2143(2) 0.04223(6) 0.89021(14) 0.0212(3) Uani 1 1 d . . . . .
H12A H 0.0695 0.0519 0.8929 0.032 Uiso 1 1 calc R U . . .
H12B H 0.2311 0.0059 0.9133 0.032 Uiso 1 1 calc R U . . .
H12C H 0.2571 0.0484 0.7962 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3060(2) 0.05923(5) 1.13799(14) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.3015 0.0210 1.1415 0.021 Uiso 1 1 calc R U . . .
C14 C 0.4845(2) 0.07545(6) 1.24104(14) 0.0206(3) Uani 1 1 d . . . . .
H14A H 0.4874 0.1132 1.2494 0.025 Uiso 1 1 calc R U . . .
H14B H 0.6162 0.0641 1.2069 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4592(2) 0.05154(6) 1.38354(15) 0.0250(3) Uani 1 1 d . . . . .
H15A H 0.4663 0.0138 1.3757 0.030 Uiso 1 1 calc R U . . .
H15B H 0.5737 0.0628 1.4510 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2550(2) 0.06656(6) 1.43802(15) 0.0241(3) Uani 1 1 d . . . . .
H16A H 0.2561 0.1037 1.4590 0.029 Uiso 1 1 calc R U . . .
H16B H 0.2381 0.0479 1.5261 0.029 Uiso 1 1 calc R U . . .
C17 C 0.0736(2) 0.05447(7) 1.33203(15) 0.0278(4) Uani 1 1 d . . . . .
H17A H -0.0545 0.0680 1.3664 0.033 Uiso 1 1 calc R U . . .
H17B H 0.0590 0.0169 1.3223 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1034(2) 0.07795(6) 1.18907(15) 0.0214(3) Uani 1 1 d . . . . .
H18A H -0.0127 0.0680 1.1211 0.026 Uiso 1 1 calc R U . . .
H18B H 0.1051 0.1157 1.1965 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3176(2) 0.23361(6) 0.51890(14) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.3515(3) 0.28554(6) 0.59141(17) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.2854 0.2855 0.6794 0.039 Uiso 1 1 calc R U . . .
H8B H 0.2912 0.3126 0.5302 0.039 Uiso 1 1 calc R U . . .
H8C H 0.4995 0.2917 0.6110 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0853(2) 0.22429(6) 0.49086(16) 0.0240(3) Uani 1 1 d . . . . .
H9A H 0.0617 0.1907 0.4471 0.036 Uiso 1 1 calc R U . . .
H9B H 0.0248 0.2509 0.4282 0.036 Uiso 1 1 calc R U . . .
H9C H 0.0210 0.2253 0.5794 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4089(3) 0.23589(7) 0.37733(16) 0.0275(4) Uani 1 1 d . . . . .
H10A H 0.5551 0.2449 0.3916 0.041 Uiso 1 1 calc R U . . .
H10B H 0.3358 0.2618 0.3183 0.041 Uiso 1 1 calc R U . . .
H10C H 0.3941 0.2024 0.3314 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.3646(18) . ?
O H 0.94(2) . ?
N C12 1.4669(19) . ?
N C11 1.470(2) . ?
N C13 1.4825(19) . ?
C1 C6 1.385(2) . ?
C1 C2 1.399(2) . ?
C2 C3 1.385(2) . ?
C2 C11 1.517(2) . ?
C3 C4 1.397(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C7 1.528(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.521(2) . ?
C13 C18 1.529(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.525(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.530(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C7 C10 1.530(2) . ?
C7 C8 1.532(2) . ?
C7 C9 1.535(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C1 O H 103.5(13) . . ?
C12 N C11 110.16(11) . . ?
C12 N C13 111.77(12) . . ?
C11 N C13 114.49(11) . . ?
O C1 C6 119.46(13) . . ?
O C1 C2 120.87(13) . . ?
C6 C1 C2 119.67(13) . . ?
C3 C2 C1 118.69(13) . . ?
C3 C2 C11 120.76(13) . . ?
C1 C2 C11 120.51(13) . . ?
C2 C3 C4 122.92(13) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 116.70(13) . . ?
C5 C4 C7 122.99(13) . . ?
C3 C4 C7 120.25(13) . . ?
C6 C5 C4 121.69(14) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 120.31(14) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N C11 C2 111.07(11) . . ?
N C11 H11A 109.4 . . ?
C2 C11 H11A 109.4 . . ?
N C11 H11B 109.4 . . ?
C2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N C12 H12A 109.5 . . ?
N C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N C13 C14 111.85(12) . . ?
N C13 C18 115.92(12) . . ?
C14 C13 C18 109.66(12) . . ?
N C13 H13 106.3 . . ?
C14 C13 H13 106.3 . . ?
C18 C13 H13 106.3 . . ?
C13 C14 C15 109.44(13) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.57(13) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 111.59(13) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.35(13) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C13 C18 C17 109.81(13) . . ?
C13 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C13 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C4 C7 C10 112.00(13) . . ?
C4 C7 C8 108.67(13) . . ?
C10 C7 C8 108.47(13) . . ?
C4 C7 C9 111.17(12) . . ?
C10 C7 C9 107.69(13) . . ?
C8 C7 C9 108.75(12) . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O C1 C2 C3 -179.05(12) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
O C1 C2 C11 3.2(2) . . . . ?
C6 C1 C2 C11 -176.96(13) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C11 C2 C3 C4 176.26(12) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 C7 -176.19(12) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C7 C4 C5 C6 177.11(13) . . . . ?
O C1 C6 C5 180.00(13) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C12 N C11 C2 -70.24(15) . . . . ?
C13 N C11 C2 162.79(11) . . . . ?
C3 C2 C11 N 142.32(13) . . . . ?
C1 C2 C11 N -40.02(17) . . . . ?
C12 N C13 C14 159.25(12) . . . . ?
C11 N C13 C14 -74.61(15) . . . . ?
C12 N C13 C18 -74.04(16) . . . . ?
C11 N C13 C18 52.11(16) . . . . ?
N C13 C14 C15 -169.06(12) . . . . ?
C18 C13 C14 C15 60.90(16) . . . . ?
C13 C14 C15 C16 -57.60(17) . . . . ?
C14 C15 C16 C17 53.79(18) . . . . ?
C15 C16 C17 C18 -53.06(19) . . . . ?
N C13 C18 C17 171.70(12) . . . . ?
C14 C13 C18 C17 -60.50(16) . . . . ?
C16 C17 C18 C13 56.39(18) . . . . ?
C5 C4 C7 C10 17.37(19) . . . . ?
C3 C4 C7 C10 -165.50(13) . . . . ?
C5 C4 C7 C8 -102.44(16) . . . . ?
C3 C4 C7 C8 74.69(16) . . . . ?
C5 C4 C7 C9 137.90(14) . . . . ?
C3 C4 C7 C9 -44.97(18) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

