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

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

data_cvd364
_database_code_depnum_ccdc_archive 'CCDC 1502611'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2015-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H32 N2 O4 Zn'
_chemical_formula_sum            'C18 H32 N2 O4 Zn'
_chemical_formula_weight         405.82
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   10.1081(2)
_cell_length_b                   5.45455(12)
_cell_length_c                   17.4938(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.0814(19)
_cell_angle_gamma                90
_cell_volume                     960.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    106
_cell_measurement_theta_max      28.8029
_cell_measurement_theta_min      2.9473
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15203
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.735
_diffrn_ambient_temperature      106
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8506  -38.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881  -66.0000  177.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00  119.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8506   77.0000  -60.0000 138

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8506  179.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00  119.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8506   77.0000  120.0000 138

#__ type_ start__ end____ width___ exp.time_
  6 omega -122.00  -32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881  179.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega -122.00  -32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881  179.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega -115.00   14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881  -38.0000    0.0000 129

#__ type_ start__ end____ width___ exp.time_
  9 omega  -18.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8506   38.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0382754000
_diffrn_orient_matrix_UB_12      -0.0419855000
_diffrn_orient_matrix_UB_13      0.0294629000
_diffrn_orient_matrix_UB_21      0.0490512000
_diffrn_orient_matrix_UB_22      -0.0895608000
_diffrn_orient_matrix_UB_23      0.0106570000
_diffrn_orient_matrix_UB_31      0.0330372000
_diffrn_orient_matrix_UB_32      0.0844310000
_diffrn_orient_matrix_UB_33      0.0259847000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2052
_reflns_number_total             2173
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.4412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0572
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2500 0.44349(4) 0.2500 0.01057(8) Uani 1 2 d S T P . .
O1 O 0.28654(9) 0.22992(17) 0.33869(5) 0.01357(19) Uani 1 1 d . . . . .
C3 C 0.16375(13) 0.4769(2) 0.41983(7) 0.0134(3) Uani 1 1 d . . . . .
H3 H 0.1501 0.5026 0.4723 0.016 Uiso 1 1 calc R . . . .
N1 N 0.10317(10) 0.6336(2) 0.29192(6) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.24979(13) 0.2891(2) 0.40502(7) 0.0121(3) Uani 1 1 d . . . . .
C5 C 0.00060(13) 0.8188(3) 0.40027(8) 0.0158(3) Uani 1 1 d . . . . .
H5A H -0.0915 0.7831 0.3813 0.024 Uiso 1 1 calc GR . . . .
H5B H 0.0234 0.9857 0.3854 0.024 Uiso 1 1 calc GR . . . .
H5C H 0.0104 0.8048 0.4563 0.024 Uiso 1 1 calc GR . . . .
C4 C 0.09252(12) 0.6378(2) 0.36601(7) 0.0122(3) Uani 1 1 d . . . . .
C1 C 0.30808(14) 0.1334(3) 0.47086(8) 0.0160(3) Uani 1 1 d . . . . .
H1A H 0.2845 -0.0387 0.4610 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.2726 0.1870 0.5185 0.024 Uiso 1 1 calc GR . . . .
H1C H 0.4050 0.1507 0.4758 0.024 Uiso 1 1 calc GR . . . .
C6 C 0.02168(13) 0.8068(2) 0.24285(8) 0.0145(3) Uani 1 1 d . . . . .
H6A H 0.0616 0.9724 0.2479 0.017 Uiso 1 1 calc R . . . .
H6B H -0.0685 0.8154 0.2606 0.017 Uiso 1 1 calc R . . . .
C8 C -0.06652(13) 0.4960(3) 0.14233(8) 0.0161(3) Uani 1 1 d . . . . .
H8A H -0.0639 0.4499 0.0878 0.019 Uiso 1 1 calc R . . . .
H8B H -0.0268 0.3609 0.1745 0.019 Uiso 1 1 calc R . . . .
C7 C 0.01139(13) 0.7302(3) 0.15891(7) 0.0149(3) Uani 1 1 d . . . . .
H7A H -0.0315 0.8641 0.1275 0.018 Uiso 1 1 calc R . . . .
H7B H 0.1021 0.7081 0.1428 0.018 Uiso 1 1 calc R . . . .
O2 O -0.20043(9) 0.53490(19) 0.15885(6) 0.0187(2) Uani 1 1 d . . . . .
C9 C -0.27592(14) 0.3164(3) 0.14903(9) 0.0214(3) Uani 1 1 d . . . . .
H9A H -0.2854 0.2715 0.0946 0.032 Uiso 1 1 calc GR . . . .
H9B H -0.3640 0.3426 0.1669 0.032 Uiso 1 1 calc GR . . . .
H9C H -0.2306 0.1841 0.1788 0.032 Uiso 1 1 calc GR . . . .


_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 O1 1.9492(9) . ?
Zn1 O1 1.9492(9) 2 ?
Zn1 N1 2.0020(11) 2 ?
Zn1 N1 2.0020(11) . ?
O1 C2 1.2903(16) . ?
C3 H3 0.9500 . ?
C3 C2 1.3831(19) . ?
C3 C4 1.4332(19) . ?
N1 C4 1.3103(17) . ?
N1 C6 1.4774(16) . ?
C2 C1 1.5084(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C4 1.5155(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5213(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5153(19) . ?
C8 O2 1.4248(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O2 C9 1.4173(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O1 Zn1 O1 106.59(6) . 2 ?
O1 Zn1 N1 96.45(4) . . ?
O1 Zn1 N1 120.44(4) 2 . ?
O1 Zn1 N1 120.44(4) . 2 ?
O1 Zn1 N1 96.45(4) 2 2 ?
N1 Zn1 N1 117.62(6) . 2 ?
C2 O1 Zn1 121.12(8) . . ?
C2 C3 H3 115.9 . . ?
C2 C3 C4 128.16(12) . . ?
C4 C3 H3 115.9 . . ?
C4 N1 Zn1 119.99(9) . . ?
C4 N1 C6 118.24(11) . . ?
C6 N1 Zn1 120.77(8) . . ?
O1 C2 C3 126.14(12) . . ?
O1 C2 C1 114.93(11) . . ?
C3 C2 C1 118.92(12) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
C3 C4 C5 115.41(11) . . ?
N1 C4 C3 123.96(12) . . ?
N1 C4 C5 120.63(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 111.85(11) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H8A C8 H8B 108.3 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
O2 C8 H8A 109.9 . . ?
O2 C8 H8B 109.9 . . ?
O2 C8 C7 108.82(11) . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 C6 113.96(11) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 O2 C8 111.17(11) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C2 C3 11.97(18) . . . . ?
Zn1 O1 C2 C1 -168.31(8) . . . . ?
Zn1 N1 C4 C3 -12.56(17) . . . . ?
Zn1 N1 C4 C5 167.66(9) . . . . ?
Zn1 N1 C6 C7 29.13(14) . . . . ?
N1 C6 C7 C8 67.42(14) . . . . ?
C2 C3 C4 N1 -2.4(2) . . . . ?
C2 C3 C4 C5 177.36(13) . . . . ?
C4 C3 C2 O1 3.1(2) . . . . ?
C4 C3 C2 C1 -176.59(13) . . . . ?
C4 N1 C6 C7 -162.29(11) . . . . ?
C6 N1 C4 C3 178.77(12) . . . . ?
C6 N1 C4 C5 -1.02(18) . . . . ?
C7 C8 O2 C9 -176.23(11) . . . . ?
O2 C8 C7 C6 63.74(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cvd488_red_c2
_database_code_depnum_ccdc_archive 'CCDC 1502612'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2015-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H14 N O Zn0.5)'
_chemical_formula_sum            'C16 H28 N2 O2 Zn'
_chemical_formula_weight         345.77
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C16 H28 N2 O2'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.5697(5)
_cell_length_b                   5.67097(8)
_cell_length_c                   17.9276(4)
_cell_angle_alpha                90
_cell_angle_beta                 127.823(4)
_cell_angle_gamma                90
_cell_volume                     1732.20(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22063
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.2390
_cell_measurement_theta_min      4.0740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.0664
_exptl_crystal_size_min          0.0437
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31521
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.170
_diffrn_reflns_theta_min         4.100
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -117.00  -15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -38.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega -115.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -57.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302 -125.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302  -99.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302 -125.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  6 omega    3.00   29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   91.0000  -66.6619 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   11.00   40.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000   40.4327 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   15.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000 -167.6133 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   15.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  146.8368 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   19.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000   46.4447 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  -64.8785 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000  162.5944 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   19.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000 -121.8530 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   25.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -33.2908 111

#__ type_ start__ end____ width___ exp.time_
 15 omega   28.00  141.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -111.6591 113

#__ type_ start__ end____ width___ exp.time_
 16 omega   28.00  141.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   66.7477 113

#__ type_ start__ end____ width___ exp.time_
 17 omega   33.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  163.7476 111

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   -1.6474 113

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  154.2474 113

#__ type_ start__ end____ width___ exp.time_
 20 omega   34.00  147.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 113

#__ type_ start__ end____ width___ exp.time_
 21 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 22 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 23 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 25 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
 26 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
 27 omega   38.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 28 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
 31 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 32 omega   35.00  116.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
 33 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
 34 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 35 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
 36 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
 37 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 38 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
 39 omega   35.00  116.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
 40 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
 41 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 42 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 43 omega   35.00  116.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -30.0000 81

#__ type_ start__ end____ width___ exp.time_
 44 omega   35.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 45 omega   35.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 46 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
 47 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 48 omega   29.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
 49 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
 50 omega   38.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 51 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 52 omega   79.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 53 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000   90.0000 179

#__ type_ start__ end____ width___ exp.time_
 54 omega    8.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302   77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 55 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000 -120.0000 179

#__ type_ start__ end____ width___ exp.time_
 56 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000  120.0000 179

#__ type_ start__ end____ width___ exp.time_
 57 omega    2.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302 -125.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 58 omega   15.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302   38.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 59 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000 -180.0000 179

#__ type_ start__ end____ width___ exp.time_
 60 omega   -5.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302   19.0000 -180.0000 128

#__ type_ start__ end____ width___ exp.time_
 61 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000 -150.0000 179

#__ type_ start__ end____ width___ exp.time_
 62 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000  -90.0000 179

#__ type_ start__ end____ width___ exp.time_
 63 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000  -60.0000 179

#__ type_ start__ end____ width___ exp.time_
 64 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000  -30.0000 179

#__ type_ start__ end____ width___ exp.time_
 65 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000    0.0000 179

#__ type_ start__ end____ width___ exp.time_
 66 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000   30.0000 179

#__ type_ start__ end____ width___ exp.time_
 67 omega  -48.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302    0.0000   60.0000 179

#__ type_ start__ end____ width___ exp.time_
 68 omega    4.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000 -139.9244 29

#__ type_ start__ end____ width___ exp.time_
 69 omega   29.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000   38.6144 111

#__ type_ start__ end____ width___ exp.time_
 70 omega   29.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -15.5500 111

#__ type_ start__ end____ width___ exp.time_
 71 omega   85.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 72 omega   85.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 73

#__ type_ start__ end____ width___ exp.time_
 73 omega   83.00  158.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0544368000
_diffrn_orient_matrix_UB_12      0.0268782000
_diffrn_orient_matrix_UB_13      0.1082606000
_diffrn_orient_matrix_UB_21      -0.0628267000
_diffrn_orient_matrix_UB_22      0.1505305000
_diffrn_orient_matrix_UB_23      -0.0069739000
_diffrn_orient_matrix_UB_31      -0.0355997000
_diffrn_orient_matrix_UB_32      -0.2245551000
_diffrn_orient_matrix_UB_33      0.0082849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3524
_reflns_number_total             3572
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.225
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.202(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+1.5290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.0997
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,
 H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5000 0.91103(9) 0.5000 0.02157(18) Uani 1 2 d S T P . .
Zn2 Zn 1.0000 1.08980(9) 1.0000 0.02416(18) Uani 1 2 d S T P . .
O1 O 0.58940(13) 1.1085(6) 0.59284(16) 0.0252(5) Uani 1 1 d . . . . .
O2 O 0.95794(13) 1.2859(5) 1.04918(17) 0.0280(5) Uani 1 1 d . . . . .
N1 N 0.55288(15) 0.7274(5) 0.46017(17) 0.0207(6) Uani 1 1 d . . . . .
N2 N 0.90349(15) 0.9070(7) 0.91020(17) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.7128(2) 1.2883(7) 0.6695(2) 0.0273(7) Uani 1 1 d . . . . .
H1A H 0.6901 1.4427 0.6483 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.7584 1.2779 0.6720 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.7275 1.2607 0.7313 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.65379(18) 1.1064(7) 0.6021(2) 0.0196(6) Uani 1 1 d . . . . .
C3 C 0.67143(17) 0.9557(6) 0.5575(2) 0.0193(7) Uani 1 1 d . . . . .
H3 H 0.7206 0.9761 0.5721 0.023 Uiso 1 1 calc R . . . .
C4 C 0.62457(18) 0.7726(6) 0.4918(2) 0.0183(6) Uani 1 1 d . . . . .
C5 C 0.6630(2) 0.6257(7) 0.4598(2) 0.0278(7) Uani 1 1 d . . . . .
H5A H 0.6680 0.4657 0.4804 0.042 Uiso 1 1 calc GR . . . .
H5B H 0.7141 0.6884 0.4866 0.042 Uiso 1 1 calc GR . . . .
H5C H 0.6313 0.6298 0.3922 0.042 Uiso 1 1 calc GR . . . .
C6 C 0.50813(19) 0.5309(6) 0.3928(2) 0.0268(7) Uani 1 1 d . . . . .
H6A H 0.4764 0.4540 0.4072 0.032 Uiso 1 1 calc R . . . .
H6B H 0.5444 0.4154 0.3995 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4551(2) 0.6222(7) 0.2914(3) 0.0347(8) Uani 1 1 d . . . . .
H7A H 0.4214 0.7451 0.2862 0.042 Uiso 1 1 calc R . . . .
H7B H 0.4873 0.6910 0.2762 0.042 Uiso 1 1 calc R . . . .
C8 C 0.4053(2) 0.4307(9) 0.2218(2) 0.0328(9) Uani 1 1 d . . . . .
H8A H 0.3719 0.4962 0.1593 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.3737 0.3610 0.2369 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.4384 0.3122 0.2245 0.049 Uiso 1 1 calc GR . . . .
C9 C 0.8607(2) 1.4615(6) 1.0532(2) 0.0305(8) Uani 1 1 d . . . . .
H9A H 0.8887 1.4307 1.1192 0.046 Uiso 1 1 calc GR . . . .
H9B H 0.8053 1.4502 1.0213 0.046 Uiso 1 1 calc GR . . . .
H9C H 0.8732 1.6172 1.0449 0.046 Uiso 1 1 calc GR . . . .
C10 C 0.88410(19) 1.2842(6) 1.0125(2) 0.0212(6) Uani 1 1 d . . . . .
C11 C 0.82790(18) 1.1332(6) 0.9427(2) 0.0201(7) Uani 1 1 d . . . . .
H11 H 0.7773 1.1538 0.9238 0.024 Uiso 1 1 calc R . . . .
C12 C 0.83717(19) 0.9503(6) 0.8958(2) 0.0203(7) Uani 1 1 d . . . . .
C13 C 0.7649(2) 0.8018(7) 0.8273(2) 0.0300(7) Uani 1 1 d . . . . .
H13A H 0.7546 0.7998 0.7670 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.7207 0.8678 0.8204 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.7738 0.6437 0.8510 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.9082(2) 0.7086(6) 0.8599(2) 0.0283(7) Uani 1 1 d . . . . .
H14A H 0.8653 0.5999 0.8372 0.034 Uiso 1 1 calc R . . . .
H14B H 0.9570 0.6239 0.9033 0.034 Uiso 1 1 calc R . . . .
C15 C 0.9040(2) 0.7987(8) 0.7768(3) 0.0344(8) Uani 1 1 d . . . . .
H15A H 0.8555 0.8857 0.7342 0.041 Uiso 1 1 calc R . . . .
H15B H 0.9473 0.9061 0.7999 0.041 Uiso 1 1 calc R . . . .
C16 C 0.9074(2) 0.6017(10) 0.7237(3) 0.0314(8) Uani 1 1 d . . . . .
H16A H 0.9143 0.6659 0.6796 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.8595 0.5131 0.6901 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.9508 0.5000 0.7673 0.047 Uiso 1 1 calc GR . . . .


_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 O1 1.951(3) . ?
Zn1 O1 1.951(3) 2_656 ?
Zn1 N1 1.974(3) . ?
Zn1 N1 1.974(3) 2_656 ?
Zn2 O2 1.954(3) 2_757 ?
Zn2 O2 1.954(3) . ?
Zn2 N2 1.972(3) . ?
Zn2 N2 1.972(3) 2_757 ?
O1 C2 1.294(4) . ?
O2 C10 1.298(4) . ?
N1 C4 1.305(4) . ?
N1 C6 1.484(4) . ?
N2 C12 1.312(4) . ?
N2 C14 1.483(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.502(5) . ?
C2 C3 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.424(4) . ?
C4 C5 1.514(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.499(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C10 1.498(5) . ?
C10 C11 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.424(4) . ?
C12 C13 1.516(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.525(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.499(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
O1 Zn1 O1 109.95(18) . 2_656 ?
O1 Zn1 N1 97.09(10) . . ?
O1 Zn1 N1 97.09(10) 2_656 2_656 ?
O1 Zn1 N1 118.84(11) . 2_656 ?
O1 Zn1 N1 118.84(11) 2_656 . ?
N1 Zn1 N1 116.29(17) . 2_656 ?
O2 Zn2 O2 110.62(17) 2_757 . ?
O2 Zn2 N2 118.72(11) 2_757 . ?
O2 Zn2 N2 118.72(11) . 2_757 ?
O2 Zn2 N2 96.76(11) . . ?
O2 Zn2 N2 96.76(11) 2_757 2_757 ?
N2 Zn2 N2 116.6(2) . 2_757 ?
C2 O1 Zn1 121.7(2) . . ?
C10 O2 Zn2 122.2(2) . . ?
C4 N1 Zn1 122.2(2) . . ?
C4 N1 C6 120.5(3) . . ?
C6 N1 Zn1 117.3(2) . . ?
C12 N2 Zn2 122.7(3) . . ?
C12 N2 C14 119.7(3) . . ?
C14 N2 Zn2 117.6(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 114.2(3) . . ?
O1 C2 C3 126.1(3) . . ?
C3 C2 C1 119.7(3) . . ?
C2 C3 H3 115.6 . . ?
C2 C3 C4 128.7(3) . . ?
C4 C3 H3 115.6 . . ?
N1 C4 C3 123.6(3) . . ?
N1 C4 C5 120.4(3) . . ?
C3 C4 C5 116.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 C7 110.7(3) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.2(3) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
O2 C10 C9 115.0(3) . . ?
O2 C10 C11 125.8(3) . . ?
C11 C10 C9 119.1(3) . . ?
C10 C11 H11 115.7 . . ?
C10 C11 C12 128.6(3) . . ?
C12 C11 H11 115.7 . . ?
N2 C12 C11 123.5(3) . . ?
N2 C12 C13 120.6(3) . . ?
C11 C12 C13 115.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 C15 110.8(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.0(3) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C2 C1 173.7(2) . . . . ?
Zn1 O1 C2 C3 -6.9(5) . . . . ?
Zn1 N1 C4 C3 0.2(4) . . . . ?
Zn1 N1 C4 C5 179.5(2) . . . . ?
Zn1 N1 C6 C7 84.0(3) . . . . ?
Zn2 O2 C10 C9 -174.5(2) . . . . ?
Zn2 O2 C10 C11 6.8(5) . . . . ?
Zn2 N2 C12 C11 0.5(5) . . . . ?
Zn2 N2 C12 C13 -178.9(2) . . . . ?
Zn2 N2 C14 C15 -80.1(3) . . . . ?
O1 C2 C3 C4 0.6(6) . . . . ?
O2 C10 C11 C12 -0.1(6) . . . . ?
N1 C6 C7 C8 -176.5(3) . . . . ?
N2 C14 C15 C16 -179.2(3) . . . . ?
C1 C2 C3 C4 180.0(3) . . . . ?
C2 C3 C4 N1 3.3(5) . . . . ?
C2 C3 C4 C5 -176.0(3) . . . . ?
C4 N1 C6 C7 -96.7(4) . . . . ?
C6 N1 C4 C3 -179.0(3) . . . . ?
C6 N1 C4 C5 0.2(4) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C10 C11 C12 N2 -4.0(5) . . . . ?
C10 C11 C12 C13 175.3(3) . . . . ?
C12 N2 C14 C15 101.8(4) . . . . ?
C14 N2 C12 C11 178.4(3) . . . . ?
C14 N2 C12 C13 -0.9(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 3 -1 0.1420 -4.9959 2.9979 -1.0112 -0.3008 0.7722 -0.5037
5 -3 1 0.1420 4.9959 -2.9979 1.0112 0.3008 -0.7722 0.5037
-13 0 3 0.0332 -12.9975 -0.0008 2.9943 -0.3834 0.7956 0.4877
13 0 -3 0.0332 12.9975 0.0008 -2.9943 0.3834 -0.7956 -0.4877
-1 0 -9 0.0246 -0.9874 -0.0031 -9.0064 -1.0289 0.1244 -0.0388
1 0 9 0.0246 0.9874 0.0031 9.0064 1.0289 -0.1244 0.0388
-13 0 9 0.0287 -13.0056 0.0012 8.9981 0.2662 0.7545 0.5373
13 0 -9 0.0287 13.0056 -0.0012 -8.9981 -0.2662 -0.7545 -0.5373
-4 0 -7 0.0263 -3.9886 -0.0029 -7.0069 -0.9758 0.2990 0.0846
4 0 7 0.0263 3.9886 0.0029 7.0069 0.9758 -0.2990 -0.0846
-2 -2 9 0.1111 -2.0113 -1.9966 9.0097 0.8122 -0.2370 0.5946
2 2 -9 0.1111 2.0113 1.9966 -9.0097 -0.8122 0.2370 -0.5946
-7 0 12 0.0192 -7.0126 0.0030 12.0036 0.9179 0.3573 0.3484
1 3 6 0.1272 0.9917 3.0011 5.9969 0.7839 0.3476 -0.6595
-9 3 7 0.1225 -9.0046 3.0001 6.9916 0.3474 0.9686 -0.2952
-9 0 11 0.0220 -9.0103 0.0024 11.0018 0.7006 0.4897 0.4114
9 0 -11 0.0220 9.0103 -0.0024 -11.0018 -0.7006 -0.4897 -0.4114

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1502613'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2016-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H32 N2 O4 Zn'
_chemical_formula_sum            'C18 H32 N2 O4 Zn'
_chemical_formula_weight         405.82
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   13.2557(4)
_cell_length_b                   5.89050(10)
_cell_length_c                   13.9479(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.615(3)
_cell_angle_gamma                90
_cell_volume                     1043.62(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4927
_cell_measurement_temperature    105.5(8)
_cell_measurement_theta_max      73.8320
_cell_measurement_theta_min      5.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7792
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.061
_diffrn_reflns_theta_min         4.058
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  125.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega -124.00  -79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -99.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302   38.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00  139.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -61.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega   34.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  6 omega   31.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -94.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  9 omega   75.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   77.0000  -30.0000 83

#__ type_ start__ end____ width___ exp.time_
 10 omega   73.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  125.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega -115.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 12 omega -115.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 13 omega -115.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 14 omega   75.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   77.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 15 omega   81.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   45.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   81.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   45.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 17 omega   24.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -94.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   45.0000  150.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0642454000
_diffrn_orient_matrix_UB_12      0.1019541000
_diffrn_orient_matrix_UB_13      -0.1006383000
_diffrn_orient_matrix_UB_21      -0.0172689000
_diffrn_orient_matrix_UB_22      0.2181866000
_diffrn_orient_matrix_UB_23      0.0541045000
_diffrn_orient_matrix_UB_31      0.1014092000
_diffrn_orient_matrix_UB_32      0.1019867000
_diffrn_orient_matrix_UB_33      -0.0151414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2018
_reflns_number_total             2093
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.5225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2500 -0.07385(4) 0.7500 0.02108(12) Uani 1 2 d S T P . .
O1 O 0.15094(8) -0.27226(18) 0.78919(9) 0.0253(2) Uani 1 1 d . . . . .
O2 O 0.26470(9) 0.0808(2) 0.50308(9) 0.0291(3) Uani 1 1 d . . . . .
N1 N 0.14398(10) 0.1137(2) 0.65105(9) 0.0206(3) Uani 1 1 d . . . . .
C1 C -0.01422(13) -0.4078(3) 0.79641(13) 0.0273(3) Uani 1 1 d . . . . .
H1A H -0.0892 -0.3753 0.7671 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.0040 -0.3914 0.8693 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.0007 -0.5634 0.7796 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.05033(12) -0.2434(2) 0.75521(11) 0.0217(3) Uani 1 1 d . . . . .
C3 C -0.00102(12) -0.0811(2) 0.68738(12) 0.0228(3) Uani 1 1 d . . . . .
H3 H -0.0757 -0.0840 0.6706 0.027 Uiso 1 1 calc R . . . .
C4 C 0.04275(12) 0.0906(2) 0.63899(11) 0.0211(3) Uani 1 1 d . . . . .
C5 C -0.03596(12) 0.2493(3) 0.57138(12) 0.0268(3) Uani 1 1 d . . . . .
H5A H -0.0302 0.2382 0.5030 0.040 Uiso 1 1 calc GR . . . .
H5B H -0.0214 0.4056 0.5955 0.040 Uiso 1 1 calc GR . . . .
H5C H -0.1073 0.2070 0.5719 0.040 Uiso 1 1 calc GR . . . .
C6 C 0.18082(13) 0.3020(3) 0.60057(12) 0.0283(3) Uani 1 1 d . . . . .
H6A H 0.1899 0.4392 0.6432 0.034 Uiso 1 1 calc R . . . .
H6B H 0.1267 0.3360 0.5368 0.034 Uiso 1 1 calc R . . . .
C7 C 0.28316(12) 0.2484(3) 0.57927(12) 0.0283(3) Uani 1 1 d . . . . .
H7A H 0.3122 0.3873 0.5572 0.034 Uiso 1 1 calc R . . . .
H7B H 0.3349 0.1916 0.6407 0.034 Uiso 1 1 calc R . . . .
C8 C 0.35890(15) 0.0226(4) 0.48051(14) 0.0402(4) Uani 1 1 d . . . . .
H8A H 0.4113 -0.0356 0.5412 0.048 Uiso 1 1 calc R . . . .
H8B H 0.3888 0.1582 0.4568 0.048 Uiso 1 1 calc R . . . .
C9 C 0.3344(2) -0.1557(6) 0.4010(2) 0.0686(7) Uani 1 1 d . . . . .
H9A H 0.2836 -0.0958 0.3408 0.103 Uiso 1 1 calc GR . . . .
H9B H 0.3044 -0.2889 0.4249 0.103 Uiso 1 1 calc GR . . . .
H9C H 0.3992 -0.1993 0.3851 0.103 Uiso 1 1 calc GR . . . .


_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 O1 1.9492(11) . ?
Zn1 O1 1.9492(10) 2_556 ?
Zn1 N1 1.9979(12) . ?
Zn1 N1 1.9979(13) 2_556 ?
O1 C2 1.2926(19) . ?
O2 C7 1.420(2) . ?
O2 C8 1.414(2) . ?
N1 C4 1.311(2) . ?
N1 C6 1.4699(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.510(2) . ?
C2 C3 1.380(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.428(2) . ?
C4 C5 1.513(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.503(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.494(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O1 Zn1 O1 106.32(6) . 2_556 ?
O1 Zn1 N1 122.35(5) . 2_556 ?
O1 Zn1 N1 97.37(5) 2_556 2_556 ?
O1 Zn1 N1 122.35(5) 2_556 . ?
O1 Zn1 N1 97.36(5) . . ?
N1 Zn1 N1 112.84(7) 2_556 . ?
C2 O1 Zn1 121.71(9) . . ?
C8 O2 C7 111.16(14) . . ?
C4 N1 Zn1 121.55(10) . . ?
C4 N1 C6 119.01(13) . . ?
C6 N1 Zn1 118.93(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 114.44(13) . . ?
O1 C2 C3 126.68(14) . . ?
C3 C2 C1 118.88(14) . . ?
C2 C3 H3 115.6 . . ?
C2 C3 C4 128.86(14) . . ?
C4 C3 H3 115.6 . . ?
N1 C4 C3 123.52(14) . . ?
N1 C4 C5 120.93(13) . . ?
C3 C4 C5 115.55(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 112.24(13) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
O2 C7 C6 108.78(12) . . ?
O2 C7 H7A 109.9 . . ?
O2 C7 H7B 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 H8A 110.0 . . ?
O2 C8 H8B 110.0 . . ?
O2 C8 C9 108.50(17) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C2 C1 -177.95(10) . . . . ?
Zn1 O1 C2 C3 1.9(2) . . . . ?
Zn1 N1 C4 C3 -6.0(2) . . . . ?
Zn1 N1 C4 C5 173.89(10) . . . . ?
Zn1 N1 C6 C7 35.54(16) . . . . ?
O1 C2 C3 C4 0.1(3) . . . . ?
N1 C6 C7 O2 70.14(16) . . . . ?
C1 C2 C3 C4 179.87(15) . . . . ?
C2 C3 C4 N1 2.4(2) . . . . ?
C2 C3 C4 C5 -177.49(15) . . . . ?
C4 N1 C6 C7 -152.50(14) . . . . ?
C6 N1 C4 C3 -177.69(13) . . . . ?
C6 N1 C4 C5 2.1(2) . . . . ?
C7 O2 C8 C9 179.35(18) . . . . ?
C8 O2 C7 C6 -179.58(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cvd436
_database_code_depnum_ccdc_archive 'CCDC 1502614'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2015-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H38 N4 O2 Zn'
_chemical_formula_sum            'C20 H38 N4 O2 Zn'
_chemical_formula_weight         431.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2840 1.4300 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   10.6251(2)
_cell_length_b                   5.40880(10)
_cell_length_c                   20.3670(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.906(2)
_cell_angle_gamma                90
_cell_volume                     1140.90(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13688
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.6875
_cell_measurement_theta_min      3.0721
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20128
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.144
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   77.0000   60.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
  4 omega  -62.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881   77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega  -70.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069  -38.0000  -30.0000 129

#__ type_ start__ end____ width___ exp.time_
  6 omega  -19.00  119.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   77.0000 -120.0000 138

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069 -130.0000  -65.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega  -17.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   38.0000 -150.0000 129

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069  179.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
 10 omega -118.00  -65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2881 -140.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   34.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069  179.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069  179.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  -17.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.0069   38.0000   30.0000 129
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0452265000
_diffrn_orient_matrix_UB_12      0.0188856000
_diffrn_orient_matrix_UB_13      0.0309435000
_diffrn_orient_matrix_UB_21      -0.0491075000
_diffrn_orient_matrix_UB_22      -0.0225259000
_diffrn_orient_matrix_UB_23      0.0178094000
_diffrn_orient_matrix_UB_31      0.0153023000
_diffrn_orient_matrix_UB_32      -0.1277830000
_diffrn_orient_matrix_UB_33      0.0014352000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1947
_reflns_number_total             2016
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0563
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C6 C 0.30134(14) 1.1816(3) 0.18524(7) 0.0242(3) Uani 1 1 d . . . . .
H6A H 0.2558 1.2590 0.1425 0.029 Uiso 1 1 calc R . . . .
H6B H 0.3473 1.3135 0.2149 0.029 Uiso 1 1 calc R . . . .
C5 C 0.32616(14) 1.0944(3) 0.05068(7) 0.0252(3) Uani 1 1 d . . . . .
H5A H 0.3441 1.0295 0.0088 0.038 Uiso 1 1 calc GR . . . .
H5B H 0.3484 1.2704 0.0548 0.038 Uiso 1 1 calc GR . . . .
H5C H 0.2343 1.0736 0.0500 0.038 Uiso 1 1 calc GR . . . .
C4 C 0.40607(12) 0.9549(2) 0.11005(7) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.49258(13) 0.7749(3) 0.09372(7) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.4915 0.7584 0.0472 0.025 Uiso 1 1 calc R . . . .
N2 N 0.05596(11) 0.9238(2) 0.11218(6) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.57729(13) 0.6220(3) 0.13621(7) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.39498(10) 1.0009(2) 0.17149(5) 0.0182(2) Uani 1 1 d . . . . .
O1 O 0.59538(10) 0.61437(19) 0.20082(5) 0.0258(2) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.82543(4) 0.2500 0.01970(9) Uani 1 2 d S T P . .
C1 C 0.65899(14) 0.4426(3) 0.10749(8) 0.0274(3) Uani 1 1 d . . . . .
H1A H 0.6479 0.4728 0.0591 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.6323 0.2732 0.1147 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.7500 0.4650 0.1299 0.041 Uiso 1 1 calc GR . . . .
C9 C 0.02798(17) 0.7152(3) 0.06617(9) 0.0354(4) Uani 1 1 d . . . . .
H9A H -0.0211 0.7725 0.0222 0.053 Uiso 1 1 calc GR . . . .
H9B H -0.0229 0.5923 0.0843 0.053 Uiso 1 1 calc GR . . . .
H9C H 0.1091 0.6401 0.0609 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.13121(15) 0.8460(3) 0.17811(8) 0.0271(3) Uani 1 1 d . . . . .
H8A H 0.1943 0.7187 0.1716 0.032 Uiso 1 1 calc R . . . .
H8B H 0.0724 0.7695 0.2038 0.032 Uiso 1 1 calc R . . . .
C7 C 0.20326(15) 1.0582(3) 0.21908(7) 0.0286(3) Uani 1 1 d . . . . .
H7A H 0.2486 0.9948 0.2637 0.034 Uiso 1 1 calc R . . . .
H7B H 0.1400 1.1835 0.2265 0.034 Uiso 1 1 calc R . . . .
C10 C -0.06378(14) 1.0419(3) 0.11796(9) 0.0324(4) Uani 1 1 d . . . . .
H10A H -0.1096 1.1015 0.0736 0.049 Uiso 1 1 calc GR . . . .
H10B H -0.0446 1.1818 0.1492 0.049 Uiso 1 1 calc GR . . . .
H10C H -0.1180 0.9223 0.1350 0.049 Uiso 1 1 calc GR . . . .


_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
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N1 1.4657(18) . ?
C6 C7 1.526(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C4 1.5144(18) . ?
C4 C3 1.429(2) . ?
C4 N1 1.3067(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.377(2) . ?
N2 C9 1.455(2) . ?
N2 C8 1.4629(19) . ?
N2 C10 1.4518(19) . ?
C2 O1 1.2874(17) . ?
C2 C1 1.504(2) . ?
N1 Zn1 1.9764(11) . ?
O1 Zn1 1.9460(10) . ?
Zn1 N1 1.9763(11) 2_655 ?
Zn1 O1 1.9460(10) 2_655 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
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
H6A C6 H6B 108.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 C7 110.83(11) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
C3 C4 C5 115.39(12) . . ?
N1 C4 C5 121.03(12) . . ?
N1 C4 C3 123.58(12) . . ?
C4 C3 H3 115.6 . . ?
C2 C3 C4 128.87(13) . . ?
C2 C3 H3 115.6 . . ?
C9 N2 C8 111.05(13) . . ?
C10 N2 C9 109.70(12) . . ?
C10 N2 C8 111.18(12) . . ?
C3 C2 C1 119.74(13) . . ?
O1 C2 C3 126.09(13) . . ?
O1 C2 C1 114.17(12) . . ?
C6 N1 Zn1 116.77(9) . . ?
C4 N1 C6 121.34(11) . . ?
C4 N1 Zn1 121.87(9) . . ?
C2 O1 Zn1 122.11(9) . . ?
N1 Zn1 N1 122.60(7) 2_655 . ?
O1 Zn1 N1 97.47(4) . . ?
O1 Zn1 N1 115.68(4) . 2_655 ?
O1 Zn1 N1 97.47(4) 2_655 2_655 ?
O1 Zn1 N1 115.68(4) 2_655 . ?
O1 Zn1 O1 108.17(6) . 2_655 ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
N2 C8 C7 113.03(12) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 C6 113.16(12) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 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
C5 C4 C3 C2 179.54(14) . . . . ?
C5 C4 N1 C6 2.49(19) . . . . ?
C5 C4 N1 Zn1 -179.03(9) . . . . ?
C4 C3 C2 O1 -0.6(2) . . . . ?
C4 C3 C2 C1 179.34(13) . . . . ?
C3 C4 N1 C6 -177.82(12) . . . . ?
C3 C4 N1 Zn1 0.67(18) . . . . ?
C3 C2 O1 Zn1 0.6(2) . . . . ?
N2 C8 C7 C6 -61.32(16) . . . . ?
N1 C6 C7 C8 -57.00(16) . . . . ?
N1 C4 C3 C2 -0.2(2) . . . . ?
C1 C2 O1 Zn1 -179.30(9) . . . . ?
C9 N2 C8 C7 159.33(13) . . . . ?
C7 C6 N1 C4 118.52(14) . . . . ?
C7 C6 N1 Zn1 -60.04(13) . . . . ?
C10 N2 C8 C7 -78.22(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
