# 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_NPESAL_a
_database_code_depnum_ccdc_archive 'CCDC 983262'
_audit_update_record             
;
2014-01-23 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C15 H16 N2 O'

_chemical_formula_weight         240.30



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           7

_space_group_name_H-M_alt        'P c'

_space_group_name_Hall           'P -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'



_cell_length_a                   12.7337(3)

_cell_length_b                   11.5202(3)

_cell_length_c                   9.2042(2)

_cell_angle_alpha                90

_cell_angle_beta                 100.3390(11)

_cell_angle_gamma                90

_cell_volume                     1328.28(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    8401

_cell_measurement_theta_min      2.86

_cell_measurement_theta_max      24.84



_exptl_crystal_description       Rectangular

_exptl_crystal_colour            Brown

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.202

_exptl_crystal_F_000             512

_exptl_transmission_factor_min   ?

_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.16

_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.04

_exptl_absorpt_coefficient_mu    0.077

_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      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21170

_diffrn_reflns_av_unetI/netI     0.0200

_diffrn_reflns_av_R_equivalents  0.0229

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       14

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         1.768

_diffrn_reflns_theta_max         26.362

_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_max 0.998

_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_Laue_measured_fraction_max 0.998

_diffrn_reflns_Laue_measured_fraction_full 0.998

_diffrn_reflns_point_group_measured_fraction_max 0.980

_diffrn_reflns_point_group_measured_fraction_full 0.986

_reflns_number_total             5314

_reflns_number_gt                4550

_reflns_threshold_expression     'I > 2σ(I)'

_reflns_Friedel_coverage         0.960

_reflns_Friedel_fraction_max     0.963

_reflns_Friedel_fraction_full    0.975



_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       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_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)+(0.0618P)²+0.0475P] 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 
;

 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]

 (Parsons and Flack (2004), Acta Cryst. A60, s61).

;

_refine_ls_abs_structure_Flack   0.0(3)

_chemical_absolute_configuration ?

_refine_ls_number_reflns         5314

_refine_ls_number_parameters     327

_refine_ls_number_restraints     86

_refine_ls_R_factor_all          0.0467

_refine_ls_R_factor_gt           0.0381

_refine_ls_wR_factor_ref         0.1024

_refine_ls_wR_factor_gt          0.0916

_refine_ls_goodness_of_fit_ref   1.042

_refine_ls_restrained_S_all      1.034

_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




































































O001 O -0.04830(15) 0.00650(16) 0.8231(2) 0.0700(5) Uani 1 1 d . U . . .
H001 H -0.0137 0.0466 0.8883 0.105 Uiso 1 1 calc R U . . .
N1 N 0.18035(16) 0.33140(17) 0.9353(2) 0.0564(5) Uani 1 1 d . U . . .
H3 H 0.1211 0.3627 0.8941 0.068 Uiso 1 1 calc R U . . .
O003 O 0.03068(17) 0.54313(17) 0.8802(3) 0.0800(6) Uani 1 1 d . U . . .
H003 H 0.0540 0.5977 0.9336 0.120 Uiso 1 1 calc R U . . .
N004 N -0.00072(17) 0.18480(18) 0.9919(2) 0.0582(5) Uani 1 1 d . U . . .
N005 N 0.03277(17) 0.74006(18) 1.0111(2) 0.0611(5) Uani 1 1 d . U . . .
C1 C 0.27199(18) 0.35303(19) 0.8783(2) 0.0487(5) Uani 1 1 d . U . . .
C007 C -0.14125(19) 0.0601(2) 0.7687(3) 0.0545(5) Uani 1 1 d . U . . .
N008 N 0.25407(18) 0.8036(2) 1.0075(3) 0.0717(6) Uani 1 1 d . U . . .
H008 H 0.2523 0.7347 1.0429 0.086 Uiso 1 1 calc R U . . .
C009 C -0.0695(2) 0.5661(2) 0.8145(3) 0.0639(7) Uani 1 1 d . U . . .
C00A C 0.3658(2) 0.2890(2) 0.9203(3) 0.0595(6) Uani 1 1 d . U . . .
H00A H 0.3680 0.2299 0.9896 0.071 Uiso 1 1 calc R U . . .
C00B C -0.0659(2) 0.7521(2) 0.9511(3) 0.0561(6) Uani 1 1 d . U . . .
H00B H -0.1028 0.8171 0.9746 0.067 Uiso 1 1 calc R U . . .
C00C C 0.2718(2) 0.4401(2) 0.7724(3) 0.0620(6) Uani 1 1 d . U . . .
H00C H 0.2100 0.4829 0.7406 0.074 Uiso 1 1 calc R U . . .
C00D C -0.16614(19) 0.1691(2) 0.8239(3) 0.0542(5) Uani 1 1 d . U . . .
C00E C 0.3330(2) 0.8309(2) 0.9280(3) 0.0574(6) Uani 1 1 d . U . . .
C00F C 0.0891(2) 0.8301(3) 1.1048(3) 0.0684(7) Uani 1 1 d . U . . .
H00D H 0.1215 0.7966 1.1989 0.082 Uiso 1 1 calc R U . . .
H00F H 0.0386 0.8889 1.1235 0.082 Uiso 1 1 calc R U . . .
C00G C -0.0909(2) 0.2292(2) 0.9373(3) 0.0573(6) Uani 1 1 d . U . . .
H00G H -0.1091 0.3014 0.9706 0.069 Uiso 1 1 calc R U . . .
C00H C 0.4031(2) 0.7438(2) 0.8989(3) 0.0643(6) Uani 1 1 d . U . . .
H00H H 0.3970 0.6696 0.9361 0.077 Uiso 1 1 calc R U . . .
C00I C -0.1216(2) 0.6685(2) 0.8488(3) 0.0571(6) Uani 1 1 d . U . . .
C00J C 0.0729(2) 0.2496(3) 1.1040(3) 0.0706(7) Uani 1 1 d . U . . .
H00J H 0.0786 0.2109 1.1987 0.085 Uiso 1 1 calc R U . . .
H00K H 0.0452 0.3271 1.1135 0.085 Uiso 1 1 calc R U . . .
C00K C 0.1821(2) 0.2575(2) 1.0620(3) 0.0604(6) Uani 1 1 d . U . . .
H00L H 0.2326 0.2881 1.1447 0.073 Uiso 1 1 calc R U . . .
H00M H 0.2057 0.1805 1.0400 0.073 Uiso 1 1 calc R U . . .
C00L C 0.1748(2) 0.8860(2) 1.0334(3) 0.0660(7) Uani 1 1 d . U . . .
H00N H 0.1421 0.9207 0.9402 0.079 Uiso 1 1 calc R U . . .
H00O H 0.2091 0.9475 1.0969 0.079 Uiso 1 1 calc R U . . .
C00M C -0.2646(2) 0.2191(3) 0.7649(4) 0.0753(8) Uani 1 1 d . U . . .
H00P H -0.2829 0.2902 0.8013 0.090 Uiso 1 1 calc R U . . .
C00N C 0.4805(2) 0.7662(3) 0.8166(3) 0.0792(8) Uani 1 1 d . U . . .
H00Q H 0.5266 0.7072 0.7993 0.095 Uiso 1 1 calc R U . . .
C00O C -0.2269(2) 0.6883(3) 0.7780(3) 0.0702(7) Uani 1 1 d . U . . .
H00R H -0.2623 0.7543 0.8020 0.084 Uiso 1 1 calc R U . . .
C00P C 0.3440(3) 0.9416(3) 0.8698(3) 0.0710(7) Uani 1 1 d . U . . .
H00S H 0.2987 1.0013 0.8872 0.085 Uiso 1 1 calc R U . . .
C00Q C -0.3073(3) 0.0602(3) 0.6004(4) 0.0846(9) Uani 1 1 d . U . . .
H00T H -0.3543 0.0247 0.5244 0.101 Uiso 1 1 calc R U . . .
C00R C -0.2794(3) 0.6129(3) 0.6738(4) 0.0831(8) Uani 1 1 d . U . . .
H00U H -0.3491 0.6277 0.6268 0.100 Uiso 1 1 calc R U . . .
C00S C -0.1232(3) 0.4911(3) 0.7092(4) 0.0815(9) Uani 1 1 d . U . . .
H00V H -0.0891 0.4243 0.6848 0.098 Uiso 1 1 calc R U . . .
C00T C 0.3624(3) 0.4634(2) 0.7148(4) 0.0741(7) Uani 1 1 d . U . . .
H00W H 0.3611 0.5225 0.6456 0.089 Uiso 1 1 calc R U . . .
C00U C -0.3344(2) 0.1660(4) 0.6553(4) 0.0911(10) Uani 1 1 d . U . . .
H5 H -0.3997 0.2004 0.6178 0.109 Uiso 1 1 calc R U . . .
C00V C -0.2122(2) 0.0071(3) 0.6564(3) 0.0707(7) Uani 1 1 d . U . . .
H4 H -0.1955 -0.0643 0.6193 0.085 Uiso 1 1 calc R U . . .
C00W C 0.4552(2) 0.3129(3) 0.8596(4) 0.0735(8) Uani 1 1 d . U . . .
H00$ H 0.5168 0.2690 0.8881 0.088 Uiso 1 1 calc R U . . .
C00X C -0.2259(3) 0.5138(3) 0.6403(4) 0.0886(10) Uani 1 1 d . U . . .
H00X H -0.2604 0.4620 0.5700 0.106 Uiso 1 1 calc R U . . .
C00Y C 0.4547(3) 0.4003(3) 0.7582(4) 0.0790(8) Uani 1 1 d . U . . .
H00Y H 0.5157 0.4167 0.7195 0.095 Uiso 1 1 calc R U . . .
C00Z C 0.4903(3) 0.8752(4) 0.7592(4) 0.0859(9) Uani 1 1 d . U . . .
H00Z H 0.5426 0.8899 0.7028 0.103 Uiso 1 1 calc R U . . .
C010 C 0.4227(3) 0.9620(3) 0.7860(4) 0.0844(9) Uani 1 1 d . U . . .
H010 H 0.4295 1.0357 0.7474 0.101 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






































O001 C007 1.349(3) . ?
N1 C1 1.385(3) . ?
N1 C00K 1.441(3) . ?
O003 C009 1.336(4) . ?
N004 C00G 1.275(3) . ?
N004 C00J 1.467(3) . ?
N005 C00B 1.287(3) . ?
N005 C00F 1.453(4) . ?
C1 C00A 1.398(3) . ?
C1 C00C 1.398(3) . ?
C007 C00V 1.387(4) . ?
C007 C00D 1.411(3) . ?
N008 C00E 1.382(4) . ?
N008 C00L 1.436(3) . ?
C009 C00S 1.384(5) . ?
C009 C00I 1.417(3) . ?
C00A C00W 1.383(4) . ?
C00B C00I 1.441(4) . ?
C00C C00T 1.379(4) . ?
C00D C00M 1.398(4) . ?
C00D C00G 1.459(4) . ?
C00E C00P 1.399(4) . ?
C00E C00H 1.400(4) . ?
C00F C00L 1.516(4) . ?
C00H C00N 1.371(4) . ?
C00I C00O 1.400(4) . ?
C00J C00K 1.511(4) . ?
C00M C00U 1.364(5) . ?
C00N C00Z 1.377(5) . ?
C00O C00R 1.376(5) . ?
C00P C010 1.390(4) . ?
C00Q C00V 1.372(5) . ?
C00Q C00U 1.387(6) . ?
C00R C00X 1.392(5) . ?
C00S C00X 1.373(5) . ?
C00T C00Y 1.379(5) . ?
C00W C00Y 1.372(5) . ?
C00Z C010 1.371(5) . ?



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 N1 C00K 121.40(19) . . ?
C00G N004 C00J 119.3(2) . . ?
C00B N005 C00F 121.2(2) . . ?
N1 C1 C00A 122.4(2) . . ?
N1 C1 C00C 119.8(2) . . ?
C00A C1 C00C 117.8(2) . . ?
O001 C007 C00V 119.1(2) . . ?
O001 C007 C00D 120.8(2) . . ?
C00V C007 C00D 120.1(2) . . ?
C00E N008 C00L 122.5(2) . . ?
O003 C009 C00S 120.3(3) . . ?
O003 C009 C00I 120.7(3) . . ?
C00S C009 C00I 118.9(3) . . ?
C00W C00A C1 120.5(2) . . ?
N005 C00B C00I 122.5(2) . . ?
C00T C00C C1 120.7(2) . . ?
C00M C00D C007 118.1(3) . . ?
C00M C00D C00G 120.7(2) . . ?
C007 C00D C00G 121.2(2) . . ?
N008 C00E C00P 122.8(2) . . ?
N008 C00E C00H 119.2(2) . . ?
C00P C00E C00H 118.0(3) . . ?
N005 C00F C00L 111.3(2) . . ?
N004 C00G C00D 121.4(2) . . ?
C00N C00H C00E 121.2(3) . . ?
C00O C00I C009 118.7(3) . . ?
C00O C00I C00B 120.9(2) . . ?
C009 C00I C00B 120.5(2) . . ?
N004 C00J C00K 110.6(2) . . ?
N1 C00K C00J 111.2(2) . . ?
N008 C00L C00F 111.9(2) . . ?
C00U C00M C00D 121.5(3) . . ?
C00H C00N C00Z 120.5(3) . . ?
C00R C00O C00I 121.8(3) . . ?
C010 C00P C00E 119.9(3) . . ?
C00V C00Q C00U 121.0(3) . . ?
C00O C00R C00X 118.5(3) . . ?
C00X C00S C009 121.0(3) . . ?
C00C C00T C00Y 120.9(3) . . ?
C00M C00U C00Q 119.4(3) . . ?
C00Q C00V C007 119.8(3) . . ?
C00Y C00W C00A 121.2(3) . . ?
C00S C00X C00R 121.1(3) . . ?
C00W C00Y C00T 118.9(3) . . ?
C010 C00Z C00N 119.6(3) . . ?
C00Z C010 C00P 121.0(3) . . ?



_refine_diff_density_max         0.161

_refine_diff_density_min         -0.216

_refine_diff_density_rms         0.047

#************************************END******************************


####################################################################### 
# 
# 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_NPZn_1_b
_database_code_depnum_ccdc_archive 'CCDC 1029616'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 N4 O2 Zn'
_chemical_formula_weight         543.95

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   20.9597(10)
_cell_length_b                   5.8865(3)
_cell_length_c                   21.8889(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.264(5)
_cell_angle_gamma                90
_cell_volume                     2617.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3505
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      21.83

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.973
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22412
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6305
_reflns_number_gt                4332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.974

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0377P)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 
;
 Flack x determined using 1748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.40(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6305
_refine_ls_number_parameters     334
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.110
_refine_ls_shift/su_mean         0.015

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
Zn01 Zn 0.50009(12) 0.58669(7) 0.50018(12) 0.03901(15) Uani 1 1 d . . . . .
N4 N 0.4396(5) 0.3946(14) 0.4341(5) 0.039(2) Uani 1 1 d . . . . .
O003 O 0.5688(3) 0.7729(12) 0.4811(4) 0.043(2) Uani 1 1 d . . . . .
N2 N 0.4583(6) 0.0336(16) 0.6437(5) 0.056(3) Uani 1 1 d . . . . .
H5 H 0.4639 -0.0906 0.6250 0.067 Uiso 1 1 calc R U . . .
O1 O 0.4331(3) 0.7722(14) 0.5208(4) 0.049(2) Uani 1 1 d . . . . .
C3 C 0.4171(6) 0.034(2) 0.6850(6) 0.043(3) Uani 1 1 d . . . . .
C5 C 0.4620(6) 0.1893(18) 0.4088(6) 0.047(3) Uani 1 1 d . . . . .
H5A H 0.4242 0.1070 0.3843 0.056 Uiso 1 1 calc R U . . .
H5B H 0.4842 0.0924 0.4434 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3801(7) 0.4492(18) 0.4146(6) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.3548 0.3532 0.3844 0.051 Uiso 1 1 calc R U . . .
C1 C 0.2415(7) 0.851(2) 0.4061(7) 0.058(3) Uani 1 1 d . . . . .
H1 H 0.1983 0.8680 0.3827 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3327(7) -0.008(3) 0.7642(7) 0.064(4) Uani 1 1 d . . . . .
H2 H 0.3042 -0.0182 0.7905 0.077 Uiso 1 1 calc R U . . .
C00B C 0.6259(6) 0.7968(16) 0.5162(6) 0.038(3) Uani 1 1 d . . . . .
C00C C 0.3460(5) 0.6364(18) 0.4322(5) 0.035(3) Uani 1 1 d . . . . .
C00D C 0.3328(6) 0.9838(16) 0.4933(6) 0.046(3) Uani 1 1 d . . . . .
H00D H 0.3495 1.0861 0.5256 0.055 Uiso 1 1 calc R U . . .
C00E C 0.3367(7) -0.183(3) 0.7228(8) 0.069(4) Uani 1 1 d . . . . .
H00E H 0.3105 -0.3115 0.7206 0.083 Uiso 1 1 calc R U . . .
C00F C 0.5104(6) 0.243(2) 0.3659(6) 0.054(3) Uani 1 1 d . . . . .
H00A H 0.4860 0.3023 0.3255 0.065 Uiso 1 1 calc R U . . .
H00B H 0.5423 0.3567 0.3860 0.065 Uiso 1 1 calc R U . . .
C00G C 0.6222(6) 0.4537(19) 0.5857(6) 0.039(3) Uani 1 1 d . . . . .
H00G H 0.6482 0.3523 0.6137 0.047 Uiso 1 1 calc R U . . .
C00H C 0.3714(5) 0.7951(18) 0.4811(6) 0.036(3) Uani 1 1 d . . . . .
C00I C 0.6553(6) 0.6533(17) 0.5679(6) 0.038(3) Uani 1 1 d . . . . .
C00J C 0.4147(7) 0.200(2) 0.7259(7) 0.061(4) Uani 1 1 d . . . . .
H00J H 0.4411 0.3288 0.7283 0.074 Uiso 1 1 calc R U . . .
C00K C 0.2795(5) 0.685(2) 0.3962(5) 0.048(3) Uani 1 1 d . . . . .
H00K H 0.2620 0.5887 0.3626 0.058 Uiso 1 1 calc R U . . .
C00L C 0.7303(6) 1.018(2) 0.5460(7) 0.052(4) Uani 1 1 d . . . . .
H00L H 0.7544 1.1432 0.5384 0.063 Uiso 1 1 calc R U . . .
C00M C 0.3807(7) -0.162(2) 0.6842(7) 0.056(4) Uani 1 1 d . . . . .
H00M H 0.3855 -0.2813 0.6579 0.067 Uiso 1 1 calc R U . . .
C00N C 0.7181(6) 0.6790(19) 0.6026(6) 0.058(4) Uani 1 1 d . . . . .
H00N H 0.7374 0.5717 0.6327 0.069 Uiso 1 1 calc R U . . .
C00O C 0.2717(7) 1.007(2) 0.4563(7) 0.058(4) Uani 1 1 d . . . . .
H00O H 0.2471 1.1314 0.4633 0.070 Uiso 1 1 calc R U . . .
N3 N 0.5420(6) 0.0442(17) 0.3574(4) 0.049(3) Uani 1 1 d . . . . .
H3 H 0.5356 -0.0740 0.3783 0.059 Uiso 1 1 calc R U . . .
C00Q C 0.6232(7) -0.165(2) 0.3166(7) 0.056(4) Uani 1 1 d . . . . .
H00Q H 0.6239 -0.2828 0.3452 0.067 Uiso 1 1 calc R U . . .
C00R C 0.3706(9) 0.175(3) 0.7655(7) 0.081(5) Uani 1 1 d . . . . .
H00R H 0.3681 0.2916 0.7936 0.097 Uiso 1 1 calc R U . . .
C00S C 0.6662(6) 0.975(2) 0.5089(6) 0.052(3) Uani 1 1 d . . . . .
H00S H 0.6495 1.0759 0.4763 0.062 Uiso 1 1 calc R U . . .
C00T C 0.4931(6) 0.2440(17) 0.6311(6) 0.049(3) Uani 1 1 d . . . . .
H00C H 0.4611 0.3580 0.6117 0.059 Uiso 1 1 calc R U . . .
H00F H 0.5192 0.3051 0.6705 0.059 Uiso 1 1 calc R U . . .
C00U C 0.5353(6) 0.1920(17) 0.5898(6) 0.044(3) Uani 1 1 d . . . . .
H00H H 0.5110 0.1023 0.5545 0.053 Uiso 1 1 calc R U . . .
H00I H 0.5725 0.1026 0.6125 0.053 Uiso 1 1 calc R U . . .
C00V C 0.5830(7) 0.0245(19) 0.3177(6) 0.047(3) Uani 1 1 d . . . . .
C00W C 0.5885(8) 0.202(2) 0.2742(6) 0.061(4) Uani 1 1 d . . . . .
H00W H 0.5640 0.3342 0.2735 0.073 Uiso 1 1 calc R U . . .
C00X C 0.6279(8) 0.184(2) 0.2345(7) 0.064(4) Uani 1 1 d . . . . .
H00X H 0.6303 0.3028 0.2072 0.076 Uiso 1 1 calc R U . . .
C00Y C 0.7541(6) 0.8755(19) 0.5916(6) 0.053(3) Uani 1 1 d . . . . .
H00Y H 0.7957 0.9021 0.6177 0.064 Uiso 1 1 calc R U . . .
N1 N 0.5595(5) 0.4041(13) 0.5659(5) 0.036(2) Uani 1 1 d . . . . .
C010 C 0.6610(7) -0.181(2) 0.2747(8) 0.066(4) Uani 1 1 d . . . . .
H010 H 0.6851 -0.3132 0.2739 0.079 Uiso 1 1 calc R U . . .
C011 C 0.6652(9) -0.011(4) 0.2338(7) 0.078(5) Uani 1 1 d . . . . .
H011 H 0.6923 -0.0248 0.2062 0.093 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
Zn01 O1 1.918(8) . ?
Zn01 O003 1.936(8) . ?
Zn01 N1 1.973(10) . ?
Zn01 N4 2.018(10) . ?
N4 C4 1.257(17) . ?
N4 C5 1.454(13) . ?
O003 C00B 1.261(13) . ?
N2 C3 1.396(15) . ?
N2 C00T 1.497(13) . ?
N2 H5 0.8600 . ?
O1 C00H 1.376(13) . ?
C3 C00J 1.337(17) . ?
C3 C00M 1.379(17) . ?
C5 C00F 1.575(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C00C 1.417(16) . ?
C4 H4 0.9300 . ?
C1 C00K 1.312(17) . ?
C1 C00O 1.451(19) . ?
C1 H1 0.9300 . ?
C2 C00R 1.34(2) . ?
C2 C00E 1.39(2) . ?
C2 H2 0.9300 . ?
C00B C00S 1.379(16) . ?
C00B C00I 1.424(16) . ?
C00C C00H 1.422(15) . ?
C00C C00K 1.450(14) . ?
C00D C00O 1.341(19) . ?
C00D C00H 1.438(15) . ?
C00D H00D 0.9300 . ?
C00E C00M 1.40(2) . ?
C00E H00E 0.9300 . ?
C00F N3 1.382(15) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00G N1 1.311(16) . ?
C00G C00I 1.465(16) . ?
C00G H00G 0.9300 . ?
C00I C00N 1.357(17) . ?
C00J C00R 1.42(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00Y 1.307(17) . ?
C00L C00S 1.411(18) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00Y 1.434(15) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
N3 C00V 1.369(16) . ?
N3 H3 0.8600 . ?
C00Q C010 1.36(2) . ?
C00Q C00V 1.405(17) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T C00U 1.444(15) . ?
C00T H00C 0.9700 . ?
C00T H00F 0.9700 . ?
C00U N1 1.491(13) . ?
C00U H00H 0.9700 . ?
C00U H00I 0.9700 . ?
C00V C00W 1.439(16) . ?
C00W C00X 1.341(19) . ?
C00W H00W 0.9300 . ?
C00X C011 1.39(2) . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C010 C011 1.36(2) . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?

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 Zn01 O003 110.78(11) . . ?
O1 Zn01 N1 120.4(4) . . ?
O003 Zn01 N1 95.5(3) . . ?
O1 Zn01 N4 96.9(4) . . ?
O003 Zn01 N4 122.2(4) . . ?
N1 Zn01 N4 112.92(12) . . ?
C4 N4 C5 118.0(11) . . ?
C4 N4 Zn01 119.7(8) . . ?
C5 N4 Zn01 122.3(9) . . ?
C00B O003 Zn01 125.3(7) . . ?
C3 N2 C00T 121.8(10) . . ?
C3 N2 H5 119.1 . . ?
C00T N2 H5 119.1 . . ?
C00H O1 Zn01 122.4(7) . . ?
C00J C3 C00M 120.6(13) . . ?
C00J C3 N2 124.3(11) . . ?
C00M C3 N2 114.9(12) . . ?
N4 C5 C00F 112.0(10) . . ?
N4 C5 H5A 109.2 . . ?
C00F C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C00F C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N4 C4 C00C 129.2(13) . . ?
N4 C4 H4 115.4 . . ?
C00C C4 H4 115.4 . . ?
C00K C1 C00O 115.3(12) . . ?
C00K C1 H1 122.4 . . ?
C00O C1 H1 122.3 . . ?
C00R C2 C00E 118.9(14) . . ?
C00R C2 H2 120.6 . . ?
C00E C2 H2 120.5 . . ?
O003 C00B C00S 122.1(11) . . ?
O003 C00B C00I 125.2(10) . . ?
C00S C00B C00I 112.7(11) . . ?
C4 C00C C00H 126.5(11) . . ?
C4 C00C C00K 119.2(12) . . ?
C00H C00C C00K 114.3(10) . . ?
C00O C00D C00H 117.6(12) . . ?
C00O C00D H00D 121.2 . . ?
C00H C00D H00D 121.2 . . ?
C2 C00E C00M 118.9(15) . . ?
C2 C00E H00E 120.6 . . ?
C00M C00E H00E 120.6 . . ?
N3 C00F C5 108.0(9) . . ?
N3 C00F H00A 110.1 . . ?
C5 C00F H00A 110.1 . . ?
N3 C00F H00B 110.1 . . ?
C5 C00F H00B 110.1 . . ?
H00A C00F H00B 108.4 . . ?
N1 C00G C00I 126.3(12) . . ?
N1 C00G H00G 116.9 . . ?
C00I C00G H00G 116.8 . . ?
O1 C00H C00C 122.1(9) . . ?
O1 C00H C00D 116.3(10) . . ?
C00C C00H C00D 121.5(11) . . ?
C00N C00I C00B 123.2(11) . . ?
C00N C00I C00G 113.4(12) . . ?
C00B C00I C00G 123.2(11) . . ?
C3 C00J C00R 118.0(13) . . ?
C3 C00J H00J 121.0 . . ?
C00R C00J H00J 121.0 . . ?
C1 C00K C00C 126.7(12) . . ?
C1 C00K H00K 116.6 . . ?
C00C C00K H00K 116.7 . . ?
C00Y C00L C00S 116.9(12) . . ?
C00Y C00L H00L 121.6 . . ?
C00S C00L H00L 121.6 . . ?
C3 C00M C00E 120.7(15) . . ?
C3 C00M H00M 119.7 . . ?
C00E C00M H00M 119.7 . . ?
C00I C00N C00Y 118.3(11) . . ?
C00I C00N H00N 120.8 . . ?
C00Y C00N H00N 120.8 . . ?
C00D C00O C1 124.4(12) . . ?
C00D C00O H00O 117.8 . . ?
C1 C00O H00O 117.8 . . ?
C00V N3 C00F 123.7(10) . . ?
C00V N3 H3 118.2 . . ?
C00F N3 H3 118.2 . . ?
C010 C00Q C00V 121.3(14) . . ?
C010 C00Q H00Q 119.3 . . ?
C00V C00Q H00Q 119.3 . . ?
C2 C00R C00J 122.8(15) . . ?
C2 C00R H00R 118.6 . . ?
C00J C00R H00R 118.6 . . ?
C00B C00S C00L 126.6(13) . . ?
C00B C00S H00S 116.7 . . ?
C00L C00S H00S 116.7 . . ?
C00U C00T N2 109.9(8) . . ?
C00U C00T H00C 109.7 . . ?
N2 C00T H00C 109.7 . . ?
C00U C00T H00F 109.7 . . ?
N2 C00T H00F 109.7 . . ?
H00C C00T H00F 108.2 . . ?
C00T C00U N1 110.9(9) . . ?
C00T C00U H00H 109.5 . . ?
N1 C00U H00H 109.5 . . ?
C00T C00U H00I 109.5 . . ?
N1 C00U H00I 109.5 . . ?
H00H C00U H00I 108.1 . . ?
N3 C00V C00Q 123.5(13) . . ?
N3 C00V C00W 121.6(11) . . ?
C00Q C00V C00W 114.9(13) . . ?
C00X C00W C00V 122.2(13) . . ?
C00X C00W H00W 118.9 . . ?
C00V C00W H00W 118.9 . . ?
C00W C00X C011 120.7(14) . . ?
C00W C00X H00X 119.6 . . ?
C011 C00X H00X 119.6 . . ?
C00L C00Y C00N 122.0(12) . . ?
C00L C00Y H00Y 119.0 . . ?
C00N C00Y H00Y 119.0 . . ?
C00G N1 C00U 118.1(11) . . ?
C00G N1 Zn01 121.4(8) . . ?
C00U N1 Zn01 120.2(8) . . ?
C011 C010 C00Q 122.6(14) . . ?
C011 C010 H010 118.7 . . ?
C00Q C010 H010 118.7 . . ?
C010 C011 C00X 118.1(14) . . ?
C010 C011 H011 120.9 . . ?
C00X C011 H011 120.9 . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
