# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_161018a_0m
_database_code_depnum_ccdc_archive 'CCDC 1916894'
loop_
_audit_author_name
_audit_author_address
'Min Shao'
;Shanghai University
China
;
_audit_update_record             
;
2019-05-18 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N2 O6 Zn'
_chemical_formula_weight         376.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   17.23(3)
_cell_length_b                   19.96(3)
_cell_length_c                   9.432(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.708(18)
_cell_angle_gamma                90.00
_cell_volume                     3123(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5528
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.62

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_T_max  0.7947
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7748
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2764
_reflns_number_gt                2590
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0398P)²+17.6237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.23358(2) 0.32092(2) 0.47365(5) 0.02599(17) Uani 1 1 d . . .
C1 C 0.3043(2) 0.2731(2) 0.7805(4) 0.0294(8) Uani 1 1 d . . .
C2 C 0.3393(2) 0.2888(2) 0.9462(4) 0.0280(8) Uani 1 1 d . . .
H2 H 0.2936 0.2998 0.9854 0.034 Uiso 1 1 calc R . .
C3 C 0.3830(2) 0.2292(2) 1.0353(5) 0.0355(9) Uani 1 1 d . . .
H3A H 0.3502 0.1894 1.0074 0.043 Uiso 1 1 calc R . .
H3B H 0.3888 0.2374 1.1390 0.043 Uiso 1 1 calc R . .
C4 C 0.4666(2) 0.2162(2) 1.0129(5) 0.0392(10) Uani 1 1 d . . .
H4A H 0.4933 0.1813 1.0803 0.047 Uiso 1 1 calc R . .
H4B H 0.4605 0.2002 0.9133 0.047 Uiso 1 1 calc R . .
C5 C 0.5189(2) 0.2792(2) 1.0389(4) 0.0285(8) Uani 1 1 d . . .
H5 H 0.5242 0.2934 1.1405 0.034 Uiso 1 1 calc R . .
C6 C 0.4747(2) 0.3356(2) 0.9381(5) 0.0337(9) Uani 1 1 d . . .
H6A H 0.5078 0.3756 0.9543 0.040 Uiso 1 1 calc R . .
H6B H 0.4655 0.3224 0.8360 0.040 Uiso 1 1 calc R . .
C7 C 0.3941(2) 0.3508(2) 0.9693(5) 0.0341(9) Uani 1 1 d . . .
H7A H 0.3672 0.3865 0.9045 0.041 Uiso 1 1 calc R . .
H7B H 0.4037 0.3663 1.0700 0.041 Uiso 1 1 calc R . .
C8 C 0.6043(2) 0.2685(2) 1.0242(4) 0.0331(9) Uani 1 1 d . . .
C9 C 0.1512(2) 0.43992(19) 0.3124(4) 0.0287(8) Uani 1 1 d . . .
H9 H 0.1208 0.4074 0.2514 0.034 Uiso 1 1 calc R . .
C10 C 0.1362(2) 0.5075(2) 0.2746(4) 0.0307(9) Uani 1 1 d . . .
C11 C 0.1824(3) 0.5553(2) 0.3679(5) 0.0392(10) Uani 1 1 d . . .
H11 H 0.1754 0.6006 0.3443 0.047 Uiso 1 1 calc R . .
C12 C 0.2388(3) 0.5356(2) 0.4958(5) 0.0411(10) Uani 1 1 d . . .
H12 H 0.2685 0.5673 0.5605 0.049 Uiso 1 1 calc R . .
C13 C 0.2501(2) 0.4680(2) 0.5251(5) 0.0354(9) Uani 1 1 d . . .
H13 H 0.2879 0.4547 0.6108 0.042 Uiso 1 1 calc R . .
C14 C 0.0745(3) 0.5274(2) 0.1410(5) 0.0386(10) Uani 1 1 d . . .
H14 H 0.0697 0.5723 0.1136 0.046 Uiso 1 1 calc R . .
N1 N 0.20801(19) 0.42042(16) 0.4333(4) 0.0274(7) Uani 1 1 d . . .
N2 N 0.0274(2) 0.48475(19) 0.0617(4) 0.0421(9) Uani 1 1 d . . .
O1 O 0.2779(2) 0.32276(16) 0.6981(3) 0.0492(9) Uani 1 1 d . . .
O2 O 0.3025(2) 0.21411(16) 0.7389(3) 0.0461(8) Uani 1 1 d . . .
O3 O 0.64921(18) 0.31920(18) 1.0408(4) 0.0534(9) Uani 1 1 d . . .
O4 O 0.62480(19) 0.21085(18) 0.9989(4) 0.0554(10) Uani 1 1 d . . .
O1W O 0.3832(6) 0.4495(5) 0.3369(11) 0.186(4) Uani 1 1 d . . .
O2W O 0.4797(16) 0.4990(6) 0.1544(17) 0.429(16) Uani 1 1 d . . .
H1WA H 0.3828 0.4158 0.3916 0.514 Uiso 1 1 d R . .
H1WB H 0.4044 0.4108 0.3472 0.514 Uiso 1 1 d R . .
H2WB H 0.4832 0.4597 0.1217 0.514 Uiso 1 1 d R . .
H2WA H 0.5294 0.4893 0.1871 0.514 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.047(4) . ?
Zn1 N1 2.048(4) . ?
Zn1 O4 2.053(4) 8_455 ?
Zn1 O2 2.054(4) 7_556 ?
Zn1 O3 2.061(4) 2_656 ?
Zn1 Zn1 2.903(4) 7_556 ?
C1 O2 1.238(5) . ?
C1 O1 1.266(5) . ?
C1 C2 1.548(6) . ?
C2 C3 1.531(6) . ?
C2 C7 1.536(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.533(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.528(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.530(6) . ?
C5 C6 1.537(6) . ?
C5 H5 0.9800 . ?
C6 C7 1.524(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O4 1.245(6) . ?
C8 O3 1.258(6) . ?
C9 N1 1.344(5) . ?
C9 C10 1.402(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(6) . ?
C10 C14 1.466(6) . ?
C11 C12 1.385(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(7) . ?
C12 H12 0.9300 . ?
C13 N1 1.356(6) . ?
C13 H13 0.9300 . ?
C14 N2 1.270(6) . ?
C14 H14 0.9300 . ?
N2 N2 1.422(7) 5_565 ?
O2 Zn1 2.054(4) 7_556 ?
O3 Zn1 2.061(4) 2_656 ?
O4 Zn1 2.053(4) 8_556 ?
O1W H1WA 0.8487 . ?
O1W H1WB 0.8490 . ?
O2W O2W 1.75(3) 2_655 ?
O2W H2WB 0.8500 . ?
O2W H2WA 0.8500 . ?

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 N1 100.13(13) . . ?
O1 Zn1 O4 88.97(17) . 8_455 ?
N1 Zn1 O4 99.44(15) . 8_455 ?
O1 Zn1 O2 160.91(13) . 7_556 ?
N1 Zn1 O2 98.96(14) . 7_556 ?
O4 Zn1 O2 87.91(16) 8_455 7_556 ?
O1 Zn1 O3 88.35(17) . 2_656 ?
N1 Zn1 O3 99.74(14) . 2_656 ?
O4 Zn1 O3 160.81(15) 8_455 2_656 ?
O2 Zn1 O3 88.44(16) 7_556 2_656 ?
O1 Zn1 Zn1 80.78(9) . 7_556 ?
N1 Zn1 Zn1 178.73(9) . 7_556 ?
O4 Zn1 Zn1 79.67(12) 8_455 7_556 ?
O2 Zn1 Zn1 80.14(11) 7_556 7_556 ?
O3 Zn1 Zn1 81.15(10) 2_656 7_556 ?
O2 C1 O1 125.2(4) . . ?
O2 C1 C2 118.8(4) . . ?
O1 C1 C2 116.0(4) . . ?
C3 C2 C7 110.8(3) . . ?
C3 C2 C1 113.3(4) . . ?
C7 C2 C1 111.3(3) . . ?
C3 C2 H2 107.0 . . ?
C7 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C2 C3 C4 113.4(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 111.9(4) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C8 114.2(4) . . ?
C4 C5 C6 109.4(3) . . ?
C8 C5 C6 112.0(3) . . ?
C4 C5 H5 106.9 . . ?
C8 C5 H5 106.9 . . ?
C6 C5 H5 106.9 . . ?
C7 C6 C5 110.6(3) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C2 111.7(3) . . ?
C6 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O4 C8 O3 124.8(4) . . ?
O4 C8 C5 118.4(4) . . ?
O3 C8 C5 116.8(4) . . ?
N1 C9 C10 122.4(4) . . ?
N1 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 117.7(4) . . ?
C11 C10 C14 121.0(4) . . ?
C9 C10 C14 121.3(4) . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 118.6(4) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N1 C13 C12 122.4(4) . . ?
N1 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
N2 C14 C10 121.6(4) . . ?
N2 C14 H14 119.2 . . ?
C10 C14 H14 119.2 . . ?
C9 N1 C13 118.6(4) . . ?
C9 N1 Zn1 120.6(3) . . ?
C13 N1 Zn1 120.7(3) . . ?
C14 N2 N2 111.8(5) . 5_565 ?
C1 O1 Zn1 126.3(3) . . ?
C1 O2 Zn1 127.4(3) . 7_556 ?
C8 O3 Zn1 125.9(3) . 2_656 ?
C8 O4 Zn1 128.5(3) . 8_556 ?
H1WA O1W H1WB 44.2 . . ?
O2W O2W H2WB 109.1 2_655 . ?
O2W O2W H2WA 62.8 2_655 . ?
H2WB O2W H2WA 76.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O3 0.85 2.15 2.959(10) 159.3 2_656
O1W H1WA O3 0.85 2.15 2.959(10) 159.3 2_656
O2W H2WA O1W 0.85 1.77 2.54(2) 149.7 2_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.078
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_161201a
_database_code_depnum_ccdc_archive 'CCDC 1916896'
loop_
_audit_author_name
_audit_author_address
'Min Shao'
;Shanghai University
China
;
_audit_update_record             
;
2019-05-18 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N5 O7 Zn'
_chemical_formula_weight         544.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.585(5)
_cell_length_b                   10.181(6)
_cell_length_c                   14.860(12)
_cell_angle_alpha                104.460(9)
_cell_angle_beta                 101.001(9)
_cell_angle_gamma                102.349(6)
_cell_volume                     1186.9(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4041
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.52

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8450
_exptl_absorpt_correction_T_max  0.8989
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6078
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4117
_reflns_number_gt                3783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+1.4654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4117
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.49581(4) 0.09146(3) 0.64941(2) 0.02988(12) Uani 1 1 d . . .
C1 C 0.4259(3) 0.3205(3) 0.61979(19) 0.0303(6) Uani 1 1 d . . .
C2 C 0.3590(3) 0.4171(3) 0.57184(18) 0.0275(5) Uani 1 1 d . . .
C3 C 0.4308(3) 0.5617(3) 0.60872(18) 0.0283(5) Uani 1 1 d . . .
H3 H 0.5193 0.5971 0.6632 0.034 Uiso 1 1 calc R . .
C4 C 0.3730(3) 0.6539(3) 0.56576(18) 0.0284(5) Uani 1 1 d . . .
C5 C 0.2395(3) 0.6021(3) 0.48546(19) 0.0304(6) Uani 1 1 d . . .
H5 H 0.1978 0.6628 0.4564 0.036 Uiso 1 1 calc R . .
C6 C 0.1699(3) 0.4578(3) 0.44974(19) 0.0310(6) Uani 1 1 d . . .
C7 C 0.2278(3) 0.3636(3) 0.49020(19) 0.0320(6) Uani 1 1 d . . .
H7 H 0.1802 0.2669 0.4634 0.038 Uiso 1 1 calc R . .
C8 C 0.4577(4) 0.8102(3) 0.60849(19) 0.0333(6) Uani 1 1 d . . .
C9 C 0.4953(3) 0.2097(3) 0.85661(19) 0.0338(6) Uani 1 1 d . . .
H9 H 0.5643 0.2903 0.8519 0.041 Uiso 1 1 calc R . .
C10 C 0.4675(3) 0.2115(3) 0.9456(2) 0.0373(6) Uani 1 1 d . . .
C11 C 0.3614(5) 0.0920(4) 0.9503(3) 0.0604(10) Uani 1 1 d . . .
H11 H 0.3378 0.0879 1.0082 0.072 Uiso 1 1 calc R . .
C12 C 0.2907(5) -0.0216(4) 0.8679(3) 0.0685(12) Uani 1 1 d . . .
H12 H 0.2186 -0.1024 0.8702 0.082 Uiso 1 1 calc R . .
C13 C 0.3267(4) -0.0149(3) 0.7837(2) 0.0475(8) Uani 1 1 d . . .
H13 H 0.2786 -0.0923 0.7290 0.057 Uiso 1 1 calc R . .
C14 C 0.5538(4) 0.3354(3) 1.0312(2) 0.0401(7) Uani 1 1 d . . .
C15 C 0.4913(6) 0.3563(4) 1.1193(3) 0.0782(13) Uani 1 1 d . . .
H15A H 0.5306 0.3003 1.1569 0.117 Uiso 1 1 calc R . .
H15B H 0.3729 0.3282 1.1010 0.117 Uiso 1 1 calc R . .
H15C H 0.5303 0.4541 1.1567 0.117 Uiso 1 1 calc R . .
C16 C 0.9118(3) 0.5491(3) 1.14090(19) 0.0356(6) Uani 1 1 d . . .
C17 C 1.0019(4) 0.4421(4) 1.1117(3) 0.0555(9) Uani 1 1 d . . .
H17A H 0.9288 0.3629 1.0601 0.083 Uiso 1 1 calc R . .
H17B H 1.0407 0.4110 1.1655 0.083 Uiso 1 1 calc R . .
H17C H 1.0942 0.4834 1.0905 0.083 Uiso 1 1 calc R . .
C18 C 0.9983(3) 0.6806(3) 1.22244(19) 0.0328(6) Uani 1 1 d . . .
C19 C 1.1679(3) 0.7248(3) 1.25222(19) 0.0330(6) Uani 1 1 d . . .
H19 H 1.2268 0.6700 1.2208 0.040 Uiso 1 1 calc R . .
C20 C 1.1699(4) 0.9202(3) 1.3714(2) 0.0374(6) Uani 1 1 d . . .
H20 H 1.2277 1.0025 1.4209 0.045 Uiso 1 1 calc R . .
C21 C 0.9995(4) 0.8804(3) 1.3484(2) 0.0454(7) Uani 1 1 d . . .
H21 H 0.9435 0.9340 1.3833 0.055 Uiso 1 1 calc R . .
C22 C 0.9127(4) 0.7602(3) 1.2730(2) 0.0421(7) Uani 1 1 d . . .
H22 H 0.7979 0.7331 1.2563 0.051 Uiso 1 1 calc R . .
C23 C 0.2463(8) 0.0174(11) 0.1350(4) 0.156(4) Uani 1 1 d . . .
H23A H 0.3058 0.0911 0.1147 0.234 Uiso 1 1 calc R . .
H23B H 0.2466 -0.0726 0.0950 0.234 Uiso 1 1 calc R . .
H23C H 0.2983 0.0289 0.2007 0.234 Uiso 1 1 calc R . .
N1 N 0.4290(3) 0.0995(2) 0.77686(16) 0.0334(5) Uani 1 1 d . . .
N2 N 0.6821(3) 0.4173(3) 1.02357(17) 0.0434(6) Uani 1 1 d . . .
N3 N 0.7614(3) 0.5368(3) 1.10208(17) 0.0429(6) Uani 1 1 d . . .
N4 N 1.2534(3) 0.8429(2) 1.32412(15) 0.0319(5) Uani 1 1 d . . .
N5 N 0.0279(3) 0.4010(3) 0.36467(18) 0.0438(6) Uani 1 1 d . . .
O1 O 0.3699(2) 0.18807(18) 0.57578(14) 0.0367(4) Uani 1 1 d . . .
O2 O 0.5295(3) 0.3704(2) 0.69826(14) 0.0449(5) Uani 1 1 d . . .
O3 O 0.5793(3) 0.8502(2) 0.67737(16) 0.0520(6) Uani 1 1 d . . .
O4 O 0.3934(3) 0.89225(18) 0.57114(14) 0.0373(5) Uani 1 1 d . . .
O5 O -0.0425(3) 0.4819(3) 0.33911(17) 0.0578(6) Uani 1 1 d . . .
O6 O -0.0147(4) 0.2754(3) 0.3246(2) 0.0883(11) Uani 1 1 d . . .
O1W O 0.1246(10) 0.0228(15) 0.1290(5) 0.305(7) Uani 1 1 d . . .
H1W H 0.0623 -0.0448 0.0849 0.458 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.968(2) . ?
Zn1 O4 1.977(2) 1_545 ?
Zn1 N4 2.041(3) 2_767 ?
Zn1 N1 2.069(3) . ?
C1 O2 1.235(3) . ?
C1 O1 1.280(3) . ?
C1 C2 1.497(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 C8 1.513(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 N5 1.471(4) . ?
C7 H7 0.9300 . ?
C8 O3 1.227(3) . ?
C8 O4 1.274(3) . ?
C9 N1 1.339(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(5) . ?
C10 C14 1.482(4) . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(5) . ?
C12 H12 0.9300 . ?
C13 N1 1.339(4) . ?
C13 H13 0.9300 . ?
C14 N2 1.274(4) . ?
C14 C15 1.492(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.275(4) . ?
C16 C18 1.494(4) . ?
C16 C17 1.493(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.376(4) . ?
C18 C22 1.387(4) . ?
C19 N4 1.344(3) . ?
C19 H19 0.9300 . ?
C20 N4 1.336(4) . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O1W 1.046(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N2 N3 1.392(3) . ?
N4 Zn1 2.041(3) 2_767 ?
N5 O6 1.208(3) . ?
N5 O5 1.212(3) . ?
O4 Zn1 1.977(2) 1_565 ?
O1W H1W 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O4 101.08(9) . 1_545 ?
O1 Zn1 N4 116.34(9) . 2_767 ?
O4 Zn1 N4 115.06(9) 1_545 2_767 ?
O1 Zn1 N1 110.18(9) . . ?
O4 Zn1 N1 103.05(9) 1_545 . ?
N4 Zn1 N1 110.08(9) 2_767 . ?
O2 C1 O1 123.6(2) . . ?
O2 C1 C2 119.6(2) . . ?
O1 C1 C2 116.8(2) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 120.7(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 C8 118.7(2) . . ?
C5 C4 C8 121.5(2) . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C7 123.0(2) . . ?
C5 C6 N5 119.0(2) . . ?
C7 C6 N5 118.1(2) . . ?
C6 C7 C2 118.2(2) . . ?
C6 C7 H7 120.9 . . ?
C2 C7 H7 120.9 . . ?
O3 C8 O4 124.3(2) . . ?
O3 C8 C4 118.9(2) . . ?
O4 C8 C4 116.7(2) . . ?
N1 C9 C10 124.2(3) . . ?
N1 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C11 C10 C9 116.9(3) . . ?
C11 C10 C14 122.7(3) . . ?
C9 C10 C14 120.4(3) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C13 C12 122.2(3) . . ?
N1 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
N2 C14 C10 115.6(3) . . ?
N2 C14 C15 124.2(3) . . ?
C10 C14 C15 120.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C18 115.7(3) . . ?
N3 C16 C17 124.7(3) . . ?
C18 C16 C17 119.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C22 117.3(3) . . ?
C19 C18 C16 120.7(2) . . ?
C22 C18 C16 122.0(3) . . ?
N4 C19 C18 123.7(3) . . ?
N4 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
N4 C20 C21 121.4(3) . . ?
N4 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C22 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C18 119.4(3) . . ?
C21 C22 H22 120.3 . . ?
C18 C22 H22 120.3 . . ?
O1W C23 H23A 109.5 . . ?
O1W C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1W C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 N1 C9 117.6(3) . . ?
C13 N1 Zn1 119.19(19) . . ?
C9 N1 Zn1 122.94(19) . . ?
C14 N2 N3 116.3(2) . . ?
C16 N3 N2 115.9(2) . . ?
C19 N4 C20 118.5(2) . . ?
C19 N4 Zn1 119.58(19) . 2_767 ?
C20 N4 Zn1 121.67(19) . 2_767 ?
O6 N5 O5 123.2(3) . . ?
O6 N5 C6 118.3(2) . . ?
O5 N5 C6 118.5(2) . . ?
C1 O1 Zn1 107.17(17) . . ?
C8 O4 Zn1 110.94(17) . 1_565 ?
C23 O1W H1W 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
O2 C1 C2 C3 9.3(4) . . . . ?
O1 C1 C2 C3 -171.0(2) . . . . ?
O2 C1 C2 C7 -171.7(3) . . . . ?
O1 C1 C2 C7 8.0(4) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C8 -179.2(2) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C8 C4 C5 C6 179.2(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C4 C5 C6 N5 179.9(2) . . . . ?
C5 C6 C7 C2 1.8(4) . . . . ?
N5 C6 C7 C2 -178.4(2) . . . . ?
C3 C2 C7 C6 -1.8(4) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
C3 C4 C8 O3 3.1(4) . . . . ?
C5 C4 C8 O3 -177.2(3) . . . . ?
C3 C4 C8 O4 -175.0(2) . . . . ?
C5 C4 C8 O4 4.6(4) . . . . ?
N1 C9 C10 C11 -1.5(5) . . . . ?
N1 C9 C10 C14 176.4(3) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C14 C10 C11 C12 -177.4(4) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 N1 -0.4(6) . . . . ?
C11 C10 C14 N2 159.3(3) . . . . ?
C9 C10 C14 N2 -18.5(4) . . . . ?
C11 C10 C14 C15 -19.6(5) . . . . ?
C9 C10 C14 C15 162.6(3) . . . . ?
N3 C16 C18 C19 -161.9(3) . . . . ?
C17 C16 C18 C19 19.3(4) . . . . ?
N3 C16 C18 C22 20.1(4) . . . . ?
C17 C16 C18 C22 -158.7(3) . . . . ?
C22 C18 C19 N4 -2.9(4) . . . . ?
C16 C18 C19 N4 179.1(2) . . . . ?
N4 C20 C21 C22 -1.9(5) . . . . ?
C20 C21 C22 C18 0.8(5) . . . . ?
C19 C18 C22 C21 1.4(4) . . . . ?
C16 C18 C22 C21 179.5(3) . . . . ?
C12 C13 N1 C9 -0.6(5) . . . . ?
C12 C13 N1 Zn1 173.4(3) . . . . ?
C10 C9 N1 C13 1.5(4) . . . . ?
C10 C9 N1 Zn1 -172.2(2) . . . . ?
O1 Zn1 N1 C13 102.1(2) . . . . ?
O4 Zn1 N1 C13 -5.1(2) 1_545 . . . ?
N4 Zn1 N1 C13 -128.3(2) 2_767 . . . ?
O1 Zn1 N1 C9 -84.3(2) . . . . ?
O4 Zn1 N1 C9 168.5(2) 1_545 . . . ?
N4 Zn1 N1 C9 45.3(2) 2_767 . . . ?
C10 C14 N2 N3 177.8(3) . . . . ?
C15 C14 N2 N3 -3.3(5) . . . . ?
C18 C16 N3 N2 177.5(2) . . . . ?
C17 C16 N3 N2 -3.7(5) . . . . ?
C14 N2 N3 C16 121.1(3) . . . . ?
C18 C19 N4 C20 1.9(4) . . . . ?
C18 C19 N4 Zn1 -172.8(2) . . . 2_767 ?
C21 C20 N4 C19 0.6(4) . . . . ?
C21 C20 N4 Zn1 175.2(2) . . . 2_767 ?
C5 C6 N5 O6 168.0(3) . . . . ?
C7 C6 N5 O6 -11.9(4) . . . . ?
C5 C6 N5 O5 -13.3(4) . . . . ?
C7 C6 N5 O5 166.9(3) . . . . ?
O2 C1 O1 Zn1 -5.8(3) . . . . ?
C2 C1 O1 Zn1 174.49(18) . . . . ?
O4 Zn1 O1 C1 -179.83(17) 1_545 . . . ?
N4 Zn1 O1 C1 -54.5(2) 2_767 . . . ?
N1 Zn1 O1 C1 71.68(19) . . . . ?
O3 C8 O4 Zn1 -7.8(4) . . . 1_565 ?
C4 C8 O4 Zn1 170.20(18) . . . 1_565 ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_161018b_0m
_database_code_depnum_ccdc_archive 'CCDC 1916895'
loop_
_audit_author_name
_audit_author_address
'Min Shao'
;Shanghai University
China
;
_audit_update_record             
;
2019-05-18 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N5 O8 Zn'
_chemical_formula_weight         548.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.74(3)
_cell_length_b                   8.444(15)
_cell_length_c                   19.15(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.957(17)
_cell_angle_gamma                90.00
_cell_volume                     2280(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.76

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8044
_exptl_absorpt_correction_T_max  0.8479
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9972
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3848
_reflns_number_gt                3431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1072P)²+1.1122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3848
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.04701(2) 0.12959(5) 0.187106(19) 0.02138(19) Uani 1 1 d . . .
C1 C 0.0867(2) 0.5015(4) 0.23163(16) 0.0204(7) Uani 1 1 d . . .
C2 C 0.1896(2) 0.5091(4) 0.23231(18) 0.0232(7) Uani 1 1 d . . .
C3 C 0.2232(2) 0.4188(4) 0.18344(18) 0.0220(7) Uani 1 1 d . . .
C4 C 0.3218(2) 0.4201(5) 0.1957(2) 0.0294(8) Uani 1 1 d . . .
C5 C 0.3835(3) 0.5076(5) 0.2494(2) 0.0394(10) Uani 1 1 d . . .
H5 H 0.4484 0.5048 0.2552 0.047 Uiso 1 1 calc R . .
C6 C 0.3477(3) 0.5995(5) 0.2946(2) 0.0414(10) Uani 1 1 d . . .
H6 H 0.3881 0.6611 0.3308 0.050 Uiso 1 1 calc R . .
C7 C 0.2508(3) 0.5996(5) 0.2856(2) 0.0341(9) Uani 1 1 d . . .
H7 H 0.2267 0.6619 0.3161 0.041 Uiso 1 1 calc R . .
C8 C 0.1555(2) 0.3308(5) 0.12075(18) 0.0245(8) Uani 1 1 d . . .
C9 C 0.2476(2) 0.0377(5) 0.2708(2) 0.0338(9) Uani 1 1 d . . .
H9 H 0.2389 -0.0265 0.2299 0.041 Uiso 1 1 calc R . .
C10 C 0.3377(3) 0.0558(6) 0.3160(2) 0.0387(10) Uani 1 1 d . . .
H10 H 0.3884 0.0052 0.3058 0.046 Uiso 1 1 calc R . .
C11 C 0.3524(3) 0.1503(5) 0.3772(2) 0.0313(9) Uani 1 1 d . . .
C12 C 0.2721(3) 0.2149(5) 0.3912(2) 0.0370(9) Uani 1 1 d . . .
H12 H 0.2781 0.2744 0.4332 0.044 Uiso 1 1 calc R . .
C13 C 0.1835(3) 0.1897(5) 0.3422(2) 0.0342(9) Uani 1 1 d . . .
H13 H 0.1307 0.2330 0.3523 0.041 Uiso 1 1 calc R . .
C14 C 0.4499(3) 0.1820(6) 0.4250(2) 0.0391(10) Uani 1 1 d . . .
C15 C 0.4634(4) 0.2556(11) 0.4967(3) 0.092(3) Uani 1 1 d . . .
H15A H 0.5288 0.2464 0.5249 0.138 Uiso 1 1 calc R . .
H15B H 0.4242 0.2032 0.5217 0.138 Uiso 1 1 calc R . .
H15C H 0.4463 0.3655 0.4904 0.138 Uiso 1 1 calc R . .
C16 C 0.6614(3) 0.2667(5) 0.4316(2) 0.0345(9) Uani 1 1 d . . .
C17 C 0.6311(4) 0.3724(7) 0.3671(3) 0.0637(17) Uani 1 1 d . . .
H17A H 0.5864 0.3178 0.3279 0.096 Uiso 1 1 calc R . .
H17B H 0.6854 0.4022 0.3521 0.096 Uiso 1 1 calc R . .
H17C H 0.6020 0.4656 0.3797 0.096 Uiso 1 1 calc R . .
C18 C 0.7564(2) 0.2862(5) 0.48454(19) 0.0300(8) Uani 1 1 d . . .
C19 C 0.8100(3) 0.4214(6) 0.4872(2) 0.0416(10) Uani 1 1 d . . .
H19 H 0.7895 0.5004 0.4523 0.050 Uiso 1 1 calc R . .
C20 C 0.8939(3) 0.4382(5) 0.5416(2) 0.0366(9) Uani 1 1 d . . .
H20 H 0.9291 0.5299 0.5423 0.044 Uiso 1 1 calc R . .
C21 C 0.8770(3) 0.1971(5) 0.5881(2) 0.0372(9) Uani 1 1 d . . .
H21 H 0.9008 0.1177 0.6222 0.045 Uiso 1 1 calc R . .
C22 C 0.7929(3) 0.1706(6) 0.5358(2) 0.0409(10) Uani 1 1 d . . .
H22 H 0.7606 0.0756 0.5348 0.049 Uiso 1 1 calc R . .
N1 N 0.1709(2) 0.1070(4) 0.28185(17) 0.0257(7) Uani 1 1 d . . .
N2 N 0.5182(2) 0.1408(5) 0.4005(2) 0.0428(9) Uani 1 1 d . . .
N3 N 0.6084(2) 0.1624(5) 0.4476(2) 0.0439(9) Uani 1 1 d . . .
N4 N 0.9274(2) 0.3320(4) 0.59296(16) 0.0267(7) Uani 1 1 d . . .
N5 N 0.3636(2) 0.3203(5) 0.1500(2) 0.0418(9) Uani 1 1 d . . .
O1 O 0.05413(17) 0.6219(3) 0.25505(14) 0.0253(6) Uani 1 1 d . . .
O2 O 0.04117(16) 0.3773(3) 0.21210(15) 0.0268(6) Uani 1 1 d . . .
O3 O 0.1168(2) 0.4128(4) 0.06762(15) 0.0419(7) Uani 1 1 d . . .
O4 O 0.14291(17) 0.1850(3) 0.12846(13) 0.0281(6) Uani 1 1 d . . .
O5 O 0.3139(2) 0.2793(5) 0.09091(19) 0.0598(10) Uani 1 1 d . . .
O6 O 0.4471(2) 0.2837(5) 0.1742(2) 0.0662(11) Uani 1 1 d . . .
O1W O 0.0585(2) -0.1099(3) 0.17045(14) 0.0317(6) Uani 1 1 d . . .
O2W O 0.0104(3) 0.6885(4) 0.05996(16) 0.0595(10) Uani 1 1 d . . .
H1WA H 0.0410 -0.1292 0.1251 0.071 Uiso 1 1 d R . .
H1WB H 0.0575 -0.1742 0.2046 0.071 Uiso 1 1 d R . .
H2WA H -0.0276 0.6607 0.0192 0.071 Uiso 1 1 d R . .
H2WB H 0.0585 0.6282 0.0689 0.071 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1W 2.062(4) . ?
Zn1 O4 2.099(4) . ?
Zn1 O1 2.102(4) 2_545 ?
Zn1 N4 2.147(4) 4_465 ?
Zn1 O2 2.153(4) . ?
Zn1 N1 2.175(4) . ?
C1 O2 1.243(4) . ?
C1 O1 1.261(4) . ?
C1 C2 1.514(5) . ?
C2 C7 1.379(5) . ?
C2 C3 1.405(5) . ?
C3 C4 1.402(5) . ?
C3 C8 1.514(5) . ?
C4 C5 1.373(6) . ?
C4 N5 1.474(5) . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.226(5) . ?
C8 O4 1.260(5) . ?
C9 N1 1.344(5) . ?
C9 C10 1.366(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(6) . ?
C11 C14 1.486(6) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 N1 1.316(5) . ?
C13 H13 0.9300 . ?
C14 N2 1.278(6) . ?
C14 C15 1.467(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.272(6) . ?
C16 C18 1.480(5) . ?
C16 C17 1.483(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C22 1.378(6) . ?
C18 C19 1.381(6) . ?
C19 C20 1.373(6) . ?
C19 H19 0.9300 . ?
C20 N4 1.315(5) . ?
C20 H20 0.9300 . ?
C21 N4 1.349(5) . ?
C21 C22 1.366(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N2 N3 1.383(5) . ?
N4 Zn1 2.147(4) 4_666 ?
N5 O5 1.205(5) . ?
N5 O6 1.222(5) . ?
O1 Zn1 2.102(4) 2 ?
O1W H1WA 0.8468 . ?
O1W H1WB 0.8535 . ?
O2W H2WA 0.8501 . ?
O2W H2WB 0.8500 . ?

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
O1W Zn1 O4 92.15(12) . . ?
O1W Zn1 O1 98.86(10) . 2_545 ?
O4 Zn1 O1 168.81(10) . 2_545 ?
O1W Zn1 N4 95.88(12) . 4_465 ?
O4 Zn1 N4 91.90(18) . 4_465 ?
O1 Zn1 N4 84.97(18) 2_545 4_465 ?
O1W Zn1 O2 176.05(10) . . ?
O4 Zn1 O2 88.81(11) . . ?
O1 Zn1 O2 80.35(10) 2_545 . ?
N4 Zn1 O2 87.92(12) 4_465 . ?
O1W Zn1 N1 87.50(11) . . ?
O4 Zn1 N1 86.17(18) . . ?
O1 Zn1 N1 96.30(18) 2_545 . ?
N4 Zn1 N1 176.18(11) 4_465 . ?
O2 Zn1 N1 88.74(11) . . ?
O2 C1 O1 124.0(3) . . ?
O2 C1 C2 119.3(3) . . ?
O1 C1 C2 116.5(3) . . ?
C7 C2 C3 120.8(3) . . ?
C7 C2 C1 117.9(3) . . ?
C3 C2 C1 121.2(3) . . ?
C4 C3 C2 115.7(3) . . ?
C4 C3 C8 123.2(3) . . ?
C2 C3 C8 121.0(3) . . ?
C5 C4 C3 123.9(3) . . ?
C5 C4 N5 116.9(3) . . ?
C3 C4 N5 119.2(3) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.3(4) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O3 C8 O4 126.9(4) . . ?
O3 C8 C3 114.9(4) . . ?
O4 C8 C3 118.2(3) . . ?
N1 C9 C10 123.9(4) . . ?
N1 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 117.1(3) . . ?
C10 C11 C14 120.7(4) . . ?
C12 C11 C14 122.1(4) . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N1 C13 C12 122.8(4) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
N2 C14 C15 123.5(4) . . ?
N2 C14 C11 116.7(4) . . ?
C15 C14 C11 119.8(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C18 116.0(4) . . ?
N3 C16 C17 124.1(4) . . ?
C18 C16 C17 119.9(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C18 C19 117.4(4) . . ?
C22 C18 C16 120.3(4) . . ?
C19 C18 C16 122.3(4) . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N4 C20 C19 123.8(4) . . ?
N4 C20 H20 118.1 . . ?
C19 C20 H20 118.1 . . ?
N4 C21 C22 123.6(4) . . ?
N4 C21 H21 118.2 . . ?
C22 C21 H21 118.2 . . ?
C21 C22 C18 119.2(4) . . ?
C21 C22 H22 120.4 . . ?
C18 C22 H22 120.4 . . ?
C13 N1 C9 117.4(3) . . ?
C13 N1 Zn1 123.7(3) . . ?
C9 N1 Zn1 116.5(3) . . ?
C14 N2 N3 115.8(4) . . ?
C16 N3 N2 118.4(4) . . ?
C20 N4 C21 116.4(3) . . ?
C20 N4 Zn1 124.2(3) . 4_666 ?
C21 N4 Zn1 119.1(3) . 4_666 ?
O5 N5 O6 123.6(4) . . ?
O5 N5 C4 118.5(3) . . ?
O6 N5 C4 117.9(4) . . ?
C1 O1 Zn1 127.9(2) . 2 ?
C1 O2 Zn1 146.5(2) . . ?
C8 O4 Zn1 115.2(2) . . ?
Zn1 O1W H1WA 109.5 . . ?
Zn1 O1W H1WB 119.0 . . ?
H1WA O1W H1WB 126.5 . . ?
H2WA O2W H2WB 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C7 -146.2(3) . . . . ?
O1 C1 C2 C7 30.1(5) . . . . ?
O2 C1 C2 C3 29.6(5) . . . . ?
O1 C1 C2 C3 -154.0(3) . . . . ?
C7 C2 C3 C4 3.8(5) . . . . ?
C1 C2 C3 C4 -172.0(3) . . . . ?
C7 C2 C3 C8 -174.5(3) . . . . ?
C1 C2 C3 C8 9.7(5) . . . . ?
C2 C3 C4 C5 -2.7(6) . . . . ?
C8 C3 C4 C5 175.6(4) . . . . ?
C2 C3 C4 N5 176.0(3) . . . . ?
C8 C3 C4 N5 -5.7(5) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
N5 C4 C5 C6 -178.4(4) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
C3 C2 C7 C6 -2.6(6) . . . . ?
C1 C2 C7 C6 173.2(4) . . . . ?
C5 C6 C7 C2 0.1(7) . . . . ?
C4 C3 C8 O3 -98.6(4) . . . . ?
C2 C3 C8 O3 79.6(4) . . . . ?
C4 C3 C8 O4 83.0(4) . . . . ?
C2 C3 C8 O4 -98.8(4) . . . . ?
N1 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 3.6(6) . . . . ?
C9 C10 C11 C14 -175.8(4) . . . . ?
C10 C11 C12 C13 -3.6(6) . . . . ?
C14 C11 C12 C13 175.8(4) . . . . ?
C11 C12 C13 N1 -0.2(7) . . . . ?
C10 C11 C14 N2 11.4(6) . . . . ?
C12 C11 C14 N2 -168.0(4) . . . . ?
C10 C11 C14 C15 -168.0(6) . . . . ?
C12 C11 C14 C15 12.6(7) . . . . ?
N3 C16 C18 C22 16.9(6) . . . . ?
C17 C16 C18 C22 -166.7(5) . . . . ?
N3 C16 C18 C19 -160.1(4) . . . . ?
C17 C16 C18 C19 16.2(6) . . . . ?
C22 C18 C19 C20 -2.8(6) . . . . ?
C16 C18 C19 C20 174.3(4) . . . . ?
C18 C19 C20 N4 -0.3(7) . . . . ?
N4 C21 C22 C18 0.2(7) . . . . ?
C19 C18 C22 C21 2.8(6) . . . . ?
C16 C18 C22 C21 -174.3(4) . . . . ?
C12 C13 N1 C9 4.0(6) . . . . ?
C12 C13 N1 Zn1 -157.9(3) . . . . ?
C10 C9 N1 C13 -4.0(6) . . . . ?
C10 C9 N1 Zn1 159.3(4) . . . . ?
O1W Zn1 N1 C13 -145.3(3) . . . . ?
O4 Zn1 N1 C13 122.3(3) . . . . ?
O1 Zn1 N1 C13 -46.7(3) 2_545 . . . ?
N4 Zn1 N1 C13 62.6(16) 4_465 . . . ?
O2 Zn1 N1 C13 33.4(3) . . . . ?
O1W Zn1 N1 C9 52.6(3) . . . . ?
O4 Zn1 N1 C9 -39.7(3) . . . . ?
O1 Zn1 N1 C9 151.2(3) 2_545 . . . ?
N4 Zn1 N1 C9 -99.5(15) 4_465 . . . ?
O2 Zn1 N1 C9 -128.6(3) . . . . ?
C15 C14 N2 N3 3.2(8) . . . . ?
C11 C14 N2 N3 -176.2(4) . . . . ?
C18 C16 N3 N2 179.1(4) . . . . ?
C17 C16 N3 N2 2.9(7) . . . . ?
C14 N2 N3 C16 -112.1(5) . . . . ?
C19 C20 N4 C21 3.3(6) . . . . ?
C19 C20 N4 Zn1 -170.5(3) . . . 4_666 ?
C22 C21 N4 C20 -3.3(6) . . . . ?
C22 C21 N4 Zn1 170.9(3) . . . 4_666 ?
C5 C4 N5 O5 -158.7(4) . . . . ?
C3 C4 N5 O5 22.5(6) . . . . ?
C5 C4 N5 O6 21.2(6) . . . . ?
C3 C4 N5 O6 -157.5(4) . . . . ?
O2 C1 O1 Zn1 30.6(5) . . . 2 ?
C2 C1 O1 Zn1 -145.6(2) . . . 2 ?
O1 C1 O2 Zn1 -164.0(3) . . . . ?
C2 C1 O2 Zn1 12.1(6) . . . . ?
O1W Zn1 O2 C1 60.3(17) . . . . ?
O4 Zn1 O2 C1 -43.7(4) . . . . ?
O1 Zn1 O2 C1 139.1(4) 2_545 . . . ?
N4 Zn1 O2 C1 -135.7(4) 4_465 . . . ?
N1 Zn1 O2 C1 42.5(4) . . . . ?
O3 C8 O4 Zn1 -97.2(4) . . . . ?
C3 C8 O4 Zn1 81.0(3) . . . . ?
O1W Zn1 O4 C8 176.6(2) . . . . ?
O1 Zn1 O4 C8 7.2(6) 2_545 . . . ?
N4 Zn1 O4 C8 80.6(3) 4_465 . . . ?
O2 Zn1 O4 C8 -7.2(2) . . . . ?
N1 Zn1 O4 C8 -96.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O2W 0.85 1.95 2.646(5) 138.9 1_545
O1W H1WB O1 0.85 1.98 2.796(5) 159.2 1_545
O1W H1WB O2 0.85 2.49 3.026(5) 121.5 2_545
O2W H2WA O3 0.85 1.90 2.746(5) 175.4 3_565
O2W H2WB O3 0.85 2.01 2.787(6) 150.8 .

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.127
