# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1895714'
loop_
_audit_author_name
_audit_author_address
CCDSA
;YAN AN Unversity
China
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C22 H18 N4 O4 Zn'
_chemical_formula_sum            'C22 H18 N4 O4 Zn'
_chemical_formula_weight         467.81
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410003662
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.8375(9)
_cell_length_b                   12.1648(9)
_cell_length_c                   13.9559(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.8680(10)
_cell_angle_gamma                90
_cell_volume                     1959.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6993
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.81
_cell_measurement_theta_min      2.25
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0415 before and 0.0260 after correction.
The Ratio of minimum to maximum transmission is 0.9113.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5859
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             961.6347
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10745
_diffrn_reflns_theta_full        26.3697
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.43
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -14
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -9
_reflns_number_gt                3655
_reflns_number_total             4007
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.1425
_refine_diff_density_min         -0.8052
_refine_diff_density_rms         0.1700
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             8.3723
_refine_ls_goodness_of_fit_ref   1.0468
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.0468
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1372P)²+6.3578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2030
_refine_ls_wR_factor_ref         0.2071
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C2(H2), C15(H15), C16(H16), C18(H18), C19(H19),
 C12(H12), C11(H11), C13(H13), C22(H22), C21(H21), C20(H20)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Zn1 Zn 0.54384(4) 0.35000(4) 0.53370(3) 0.0198(2) Uani 1.000000 .
O3 O 0.9286(4) 0.2900(4) 0.0882(4) 0.0619(12) Uani 1.000000 .
O4 O 1.1036(5) 0.3349(4) 0.0726(4) 0.0665(13) Uani 1.000000 .
O1 O 0.6091(4) 0.5225(5) 0.4901(4) 0.0737(15) Uani 1.000000 .
N3 N 0.4829(4) 0.3011(4) 1.2124(4) 0.0480(11) Uani 1.000000 .
N2 N 0.5998(4) 0.4032(4) 0.8542(4) 0.0493(11) Uani 1.000000 .
N1 N 0.5996(5) 0.4008(5) 0.6959(4) 0.0535(12) Uani 1.000000 .
N4 N 0.4860(5) 0.3060(5) 1.3705(4) 0.0520(12) Uani 1.000000 .
O2 O 0.7435(5) 0.3981(5) 0.5076(5) 0.0847(17) Uani 1.000000 .
C8 C 0.7092(5) 0.4951(5) 0.4868(4) 0.0464(12) Uani 1.000000 .
C10 C 1.0091(5) 0.3588(5) 0.0937(5) 0.0483(14) Uani 1.000000 .
C14 C 0.5710(5) 0.3756(5) 0.9444(4) 0.0463(13) Uani 1.000000 .
C12 C 0.6812(6) 0.4742(5) 0.7413(5) 0.0535(14) Uani 1.000000 .
C17 C 0.5137(5) 0.3247(5) 1.1225(4) 0.0458(12) Uani 1.000000 .
C11 C 0.5520(6) 0.3596(5) 0.7651(5) 0.0523(15) Uani 1.000000 .
C13 C 0.6839(5) 0.4780(5) 0.8399(5) 0.0518(14) Uani 1.000000 .
C22 C 0.3898(6) 0.2406(5) 1.2273(5) 0.0556(15) Uani 1.000000 .
C1 C 0.8334(6) 0.5466(5) 0.3667(5) 0.0554(15) Uani 1.000000 .
C21 C 0.3935(6) 0.2442(5) 1.3239(5) 0.0559(15) Uani 1.000000 .
C4 C 0.9302(5) 0.4950(5) 0.2048(5) 0.0492(13) Uani 1.000000 .
C20 C 0.5380(6) 0.3381(5) 1.3012(5) 0.0502(14) Uani 1.000000 .
C19 C 0.4617(6) 0.3392(6) 0.9459(5) 0.0584(17) Uani 1.000000 .
C15 C 0.6533(6) 0.3851(6) 1.0320(5) 0.0542(14) Uani 1.000000 .
C18 C 0.4327(6) 0.3122(7) 1.0336(5) 0.0588(16) Uani 1.000000 .
C16 C 0.6234(6) 0.3598(5) 1.1202(5) 0.0540(16) Uani 1.000000 .
C2 C 0.7977(6) 0.5999(6) 0.2779(5) 0.0588(16) Uani 1.000000 .
C3 C 0.8455(6) 0.5750(6) 0.1978(5) 0.0569(15) Uani 1.000000 .
C9 C 0.9897(7) 0.4765(5) 0.1226(5) 0.0598(17) Uani 1.000000 .
C7 C 0.7865(7) 0.5822(6) 0.4544(6) 0.0660(19) Uani 1.000000 .
C6 C 0.9148(7) 0.4639(6) 0.3723(5) 0.0647(18) Uani 1.000000 .
C5 C 0.9640(7) 0.4397(6) 0.2933(5) 0.0645(18) Uani 1.000000 .
H6 H 0.9371(7) 0.4238(6) 0.4301(5) 0.078(2) Uiso 1.000000 R
H5 H 1.0205(7) 0.3855(6) 0.2999(5) 0.077(2) Uiso 1.000000 R
H3 H 0.8202(6) 0.6126(6) 0.1389(5) 0.0683(18) Uiso 1.000000 R
H2 H 0.7404(6) 0.6535(6) 0.2713(5) 0.0705(19) Uiso 1.000000 R
H15 H 0.7280(6) 0.4083(6) 1.0316(5) 0.0651(17) Uiso 1.000000 R
H16 H 0.6786(6) 0.3668(5) 1.1788(5) 0.0648(19) Uiso 1.000000 R
H18 H 0.3590(6) 0.2856(7) 1.0334(5) 0.0706(19) Uiso 1.000000 R
H19 H 0.4065(6) 0.3325(6) 0.8873(5) 0.070(2) Uiso 1.000000 R
H12 H 0.7282(6) 0.5157(5) 0.7100(5) 0.0642(17) Uiso 1.000000 R
H11 H 0.4931(6) 0.3074(5) 0.7541(5) 0.0627(18) Uiso 1.000000 R
H13 H 0.7316(5) 0.5212(5) 0.8872(5) 0.0622(17) Uiso 1.000000 R
H22 H 0.3350(6) 0.2043(5) 1.1796(5) 0.0667(18) Uiso 1.000000 R
H21 H 0.3410(6) 0.2097(5) 1.3547(5) 0.0671(18) Uiso 1.000000 R
H20 H 0.6046(6) 0.3811(5) 1.3123(5) 0.0603(17) Uiso 1.000000 R
H9a H 1.0646(7) 0.5124(5) 0.1397(5) 0.072(2) Uiso 1.000000 R
H9b H 0.9450(7) 0.5136(5) 0.0649(5) 0.072(2) Uiso 1.000000 R
H7a H 0.7423(7) 0.6493(6) 0.4380(6) 0.079(2) Uiso 1.000000 R
H7b H 0.8510(7) 0.5982(6) 0.5089(6) 0.079(2) Uiso 1.000000 R


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 2.363(5) . ?
Zn1 O1 2.350(5) 3_666 ?
Zn1 N1 2.297(5) . ?
Zn1 N4 2.291(5) 1_554 ?
O3 C10 1.258(8) . ?
O4 C10 1.252(8) . ?
O1 C8 1.242(7) . ?
N3 C17 1.413(8) . ?
N3 C22 1.380(8) . ?
N3 C20 1.342(8) . ?
N2 C14 1.417(8) . ?
N2 C11 1.354(8) . ?
N2 C13 1.395(8) . ?
N1 C12 1.363(8) . ?
N1 C11 1.322(8) . ?
N4 C21 1.367(8) . ?
N4 C20 1.317(8) . ?
O2 C8 1.261(8) . ?
C8 C7 1.532(9) . ?
C10 C9 1.519(9) . ?
C14 C19 1.372(10) . ?
C14 C15 1.388(9) . ?
C12 C13 1.369(9) . ?
C12 H12 0.9300 . ?
C17 C18 1.397(9) . ?
C17 C16 1.374(10) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C22 C21 1.339(9) . ?
C22 H22 0.9300 . ?
C1 C2 1.379(10) . ?
C1 C7 1.516(9) . ?
C1 C6 1.384(10) . ?
C21 H21 0.9300 . ?
C4 C3 1.385(9) . ?
C4 C9 1.491(9) . ?
C4 C5 1.384(9) . ?
C20 H20 0.9300 . ?
C19 C18 1.382(10) . ?
C19 H19 0.9300 . ?
C15 C16 1.389(9) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C2 C3 1.394(10) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C6 C5 1.388(10) . ?
C6 H6 0.9300 . ?
C5 H5 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
N1 Zn1 O1 90.3(2) . 3_666 ?
N1 Zn1 O1 88.6(2) . . ?
N4 Zn1 O1 87.9(2) 1_554 3_666 ?
N4 Zn1 O1 89.7(2) 1_554 . ?
N4 Zn1 N1 177.84(19) 1_554 . ?
C8 O1 Zn1 152.0(5) . 3_666 ?
C8 O1 Zn1 98.1(4) . . ?
C22 N3 C17 128.0(5) . . ?
C20 N3 C17 125.7(5) . . ?
C20 N3 C22 106.3(5) . . ?
C11 N2 C14 126.1(6) . . ?
C13 N2 C14 127.0(5) . . ?
C13 N2 C11 106.9(5) . . ?
C12 N1 Zn1 130.8(4) . . ?
C11 N1 Zn1 122.9(4) . . ?
C11 N1 C12 106.3(5) . . ?
C21 N4 Zn1 129.2(4) . 1_556 ?
C20 N4 Zn1 125.2(4) . 1_556 ?
C20 N4 C21 105.6(5) . . ?
O2 C8 O1 120.2(6) . . ?
C7 C8 O1 117.6(6) . . ?
C7 C8 O2 122.1(6) . . ?
O4 C10 O3 122.4(6) . . ?
C9 C10 O3 119.1(6) . . ?
C9 C10 O4 118.5(6) . . ?
C19 C14 N2 120.4(6) . . ?
C15 C14 N2 120.2(6) . . ?
C15 C14 C19 119.5(6) . . ?
C13 C12 N1 110.2(6) . . ?
H12 C12 N1 124.9(4) . . ?
H12 C12 C13 124.9(4) . . ?
C18 C17 N3 120.4(6) . . ?
C16 C17 N3 121.0(6) . . ?
C16 C17 C18 118.6(6) . . ?
N1 C11 N2 111.3(6) . . ?
H11 C11 N2 124.4(4) . . ?
H11 C11 N1 124.4(4) . . ?
C12 C13 N2 105.3(5) . . ?
H13 C13 N2 127.4(3) . . ?
H13 C13 C12 127.4(4) . . ?
C21 C22 N3 106.6(6) . . ?
H22 C22 N3 126.7(3) . . ?
H22 C22 C21 126.7(4) . . ?
C7 C1 C2 119.9(6) . . ?
C6 C1 C2 117.6(6) . . ?
C6 C1 C7 122.5(7) . . ?
C22 C21 N4 109.9(6) . . ?
H21 C21 N4 125.0(3) . . ?
H21 C21 C22 125.0(4) . . ?
C9 C4 C3 120.7(6) . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 C9 121.4(6) . . ?
N4 C20 N3 111.6(6) . . ?
H20 C20 N3 124.2(4) . . ?
H20 C20 N4 124.2(4) . . ?
C18 C19 C14 120.8(6) . . ?
H19 C19 C14 119.6(4) . . ?
H19 C19 C18 119.6(4) . . ?
C16 C15 C14 119.7(6) . . ?
H15 C15 C14 120.2(4) . . ?
H15 C15 C16 120.2(4) . . ?
C19 C18 C17 120.2(6) . . ?
H18 C18 C17 119.9(4) . . ?
H18 C18 C19 119.9(4) . . ?
C15 C16 C17 121.1(6) . . ?
H16 C16 C17 119.4(4) . . ?
H16 C16 C15 119.4(4) . . ?
C3 C2 C1 121.4(6) . . ?
H2 C2 C1 119.3(4) . . ?
H2 C2 C3 119.3(4) . . ?
C2 C3 C4 120.9(7) . . ?
H3 C3 C4 119.6(4) . . ?
H3 C3 C2 119.6(4) . . ?
C4 C9 C10 118.1(5) . . ?
H9a C9 C10 107.8(4) . . ?
H9a C9 C4 107.8(4) . . ?
H9b C9 C10 107.8(4) . . ?
H9b C9 C4 107.8(4) . . ?
H9b C9 H9a 107.1 . . ?
C1 C7 C8 113.0(6) . . ?
H7a C7 C8 109.0(4) . . ?
H7a C7 C1 109.0(4) . . ?
H7b C7 C8 109.0(4) . . ?
H7b C7 C1 109.0(4) . . ?
H7b C7 H7a 107.8 . . ?
C5 C6 C1 121.3(7) . . ?
H6 C6 C1 119.3(4) . . ?
H6 C6 C5 119.3(4) . . ?
C6 C5 C4 121.1(7) . . ?
H5 C5 C4 119.4(4) . . ?
H5 C5 C6 119.4(4) . . ?

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1895715'
loop_
_audit_author_name
_audit_author_address
CCDSA
;YAN AN Unversity
China
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C22 H20 N4 O5 Zn'
_chemical_formula_sum            'C22 H20 N4 O5 Zn'
_chemical_formula_weight         485.82
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410003662
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.474(3)
_cell_length_b                   13.755(3)
_cell_length_c                   12.771(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.090(3)
_cell_angle_gamma                90
_cell_volume                     2115.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8206
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.22
_exptl_absorpt_coefficient_mu    1.204
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0641 before and 0.0242 after correction.
The Ratio of minimum to maximum transmission is 0.8570.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5252
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1001.6776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11505
_diffrn_reflns_theta_full        26.3719
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.52
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -15
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -9
_reflns_number_gt                3904
_reflns_number_total             4319
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5470
_refine_diff_density_min         -0.6232
_refine_diff_density_rms         0.1012
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             8.0975
_refine_ls_goodness_of_fit_ref   1.0371
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.0371
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0968P)²+3.5129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1570
_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 O(H,H) groups
2.a Rotating group:
 O5(H5a,H5b)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3), C15(H15), C16(H16), C18(H18), C19(H19),
 C11(H11), C20(H20), C21(H21), C22(H22), C12(H12), C13(H13)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Zn1 Zn 0.45855(3) 0.60029(2) 0.15084(3) 0.03119(16) Uani 1.000000 .
O1 O 0.6819(2) 0.5403(2) 0.3440(2) 0.0564(7) Uani 1.000000 .
O2 O 0.51303(19) 0.60462(16) 0.31722(19) 0.0343(5) Uani 1.000000 .
O3 O 0.85082(19) 0.88270(16) 0.48324(18) 0.0326(5) Uani 1.000000 .
O4 O 0.78945(16) 0.83930(15) 0.62317(16) 0.0280(4) Uani 1.000000 .
O5 O 0.61599(18) 0.55075(15) 0.1300(2) 0.0357(5) Uani 1.000000 .
N1 N 0.3980(2) 0.45625(17) 0.1523(2) 0.0276(5) Uani 1.000000 .
N2 N 0.3910(2) 0.29591(16) 0.1586(2) 0.0286(5) Uani 1.000000 .
N3 N 0.5290(2) -0.09492(16) 0.1533(2) 0.0279(5) Uani 1.000000 .
N4 N 0.5199(2) -0.25568(17) 0.1469(2) 0.0298(5) Uani 1.000000 .
C1 C 0.5628(2) 0.6926(2) 0.5206(2) 0.0324(6) Uani 1.000000 .
C2 C 0.5727(3) 0.7900(2) 0.4944(3) 0.0344(7) Uani 1.000000 .
C3 C 0.4960(4) 0.8545(3) 0.5187(5) 0.0693(13) Uani 1.000000 .
C4 C 0.4137(4) 0.8238(6) 0.5671(6) 0.094(2) Uani 1.000000 .
C5 C 0.4076(4) 0.7295(5) 0.5931(5) 0.0800(16) Uani 1.000000 .
C6 C 0.4792(3) 0.6650(4) 0.5698(3) 0.0549(10) Uani 1.000000 .
C7 C 0.6372(3) 0.6158(3) 0.4955(3) 0.0449(9) Uani 1.000000 .
C8 C 0.6088(3) 0.5847(2) 0.3754(3) 0.0322(7) Uani 1.000000 .
C9 C 0.6619(3) 0.8253(3) 0.4437(3) 0.0471(9) Uani 1.000000 .
C10 C 0.7739(2) 0.84987(19) 0.5225(2) 0.0270(6) Uani 1.000000 .
C11 C 0.4502(3) 0.3746(2) 0.1447(3) 0.0392(8) Uani 1.000000 .
C12 C 0.3009(4) 0.4285(3) 0.1714(5) 0.0718(16) Uani 1.000000 .
C13 C 0.2949(4) 0.3297(3) 0.1749(6) 0.0741(17) Uani 1.000000 .
C14 C 0.4259(3) 0.1966(2) 0.1570(2) 0.0285(6) Uani 1.000000 .
C15 C 0.3619(4) 0.1232(3) 0.1845(5) 0.0667(15) Uani 1.000000 .
C16 C 0.3967(4) 0.0270(2) 0.1833(5) 0.0684(15) Uani 1.000000 .
C17 C 0.4954(3) 0.0043(2) 0.1561(3) 0.0295(6) Uani 1.000000 .
C18 C 0.5573(3) 0.0779(2) 0.1271(3) 0.0350(7) Uani 1.000000 .
C19 C 0.5223(3) 0.1745(2) 0.1283(3) 0.0372(7) Uani 1.000000 .
C20 C 0.4653(2) -0.1748(2) 0.1553(3) 0.0295(6) Uani 1.000000 .
C21 C 0.6232(3) -0.2267(2) 0.1387(3) 0.0375(7) Uani 1.000000 .
C22 C 0.6305(3) -0.1280(2) 0.1427(3) 0.0374(7) Uani 1.000000 .
H6 H 0.4729(3) 0.5999(4) 0.5868(3) 0.0659(13) Uiso 1.000000 R
H5 H 0.3540(4) 0.7089(5) 0.6271(5) 0.096(2) Uiso 1.000000 R
H4 H 0.3632(4) 0.8683(6) 0.5813(6) 0.113(3) Uiso 1.000000 R
H3 H 0.5001(4) 0.9200(3) 0.5021(5) 0.0831(16) Uiso 1.000000 R
H15 H 0.2967(4) 0.1380(3) 0.2034(5) 0.0800(18) Uiso 1.000000 R
H16 H 0.3538(4) -0.0226(2) 0.2007(5) 0.0820(18) Uiso 1.000000 R
H18 H 0.6219(3) 0.0634(2) 0.1069(3) 0.0420(8) Uiso 1.000000 R
H19 H 0.5644(3) 0.2241(2) 0.1095(3) 0.0447(9) Uiso 1.000000 R
H5a H 0.6064(5) 0.4981(13) 0.094(2) 0.0536(8) Uiso 1.000000 GR
H5b H 0.6582(10) 0.535(2) 0.1913(4) 0.0536(8) Uiso 1.000000 GR
H11 H 0.5199(3) 0.3715(2) 0.1312(3) 0.0470(10) Uiso 1.000000 R
H20 H 0.3928(2) -0.1728(2) 0.1618(3) 0.0354(8) Uiso 1.000000 R
H21 H 0.6796(3) -0.2684(2) 0.1316(3) 0.0451(9) Uiso 1.000000 R
H22 H 0.6913(3) -0.0903(2) 0.1391(3) 0.0449(9) Uiso 1.000000 R
H7a H 0.7131(3) 0.6395(3) 0.5162(3) 0.0539(10) Uiso 1.000000 R
H7b H 0.6336(3) 0.5590(3) 0.5395(3) 0.0539(10) Uiso 1.000000 R
H9a H 0.6740(3) 0.7757(3) 0.3940(3) 0.0565(11) Uiso 1.000000 R
H9b H 0.6347(3) 0.8829(3) 0.4012(3) 0.0565(11) Uiso 1.000000 R
H12 H 0.2460(4) 0.4708(3) 0.1807(5) 0.0862(19) Uiso 1.000000 R
H13 H 0.2364(4) 0.2929(3) 0.1863(6) 0.089(2) Uiso 1.000000 R


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 O2 2.056(2) . ?
Zn1 O3 2.224(2) 4_575 ?
Zn1 O4 2.208(2) 4_575 ?
Zn1 O5 2.160(2) . ?
Zn1 N1 2.122(2) . ?
Zn1 N4 2.129(2) 1_565 ?
O1 C8 1.248(4) . ?
O2 C8 1.262(4) . ?
O3 C10 1.275(4) . ?
O4 C10 1.258(4) . ?
O5 H5a 0.8500 . ?
O5 H5b 0.8500 . ?
N1 C11 1.315(4) . ?
N1 C12 1.350(5) . ?
N2 C11 1.348(4) . ?
N2 C13 1.352(4) . ?
N2 C14 1.435(3) . ?
N3 C17 1.431(3) . ?
N3 C20 1.359(4) . ?
N3 C22 1.385(4) . ?
N4 C20 1.323(4) . ?
N4 C21 1.379(4) . ?
C1 C2 1.395(5) . ?
C1 C6 1.403(5) . ?
C1 C7 1.495(5) . ?
C2 C3 1.397(6) . ?
C2 C9 1.506(5) . ?
C3 C4 1.395(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.346(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.346(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.542(5) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C9 C10 1.532(4) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C11 H11 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.387(5) . ?
C14 C19 1.380(4) . ?
C15 C16 1.393(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(4) . ?
C18 C19 1.399(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.361(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
O3 Zn1 O2 161.08(9) 4_575 . ?
O4 Zn1 O2 101.51(8) 4_575 . ?
O4 Zn1 O3 59.58(8) 4_575 4_575 ?
O5 Zn1 O2 94.01(9) . . ?
O5 Zn1 O3 104.81(9) . 4_575 ?
O5 Zn1 O4 163.81(9) . 4_575 ?
N1 Zn1 O2 92.33(9) . . ?
N1 Zn1 O3 88.81(9) . 4_575 ?
N1 Zn1 O4 91.44(9) . 4_575 ?
N1 Zn1 O5 92.51(9) . . ?
N4 Zn1 O2 88.49(10) 1_565 . ?
N4 Zn1 O3 90.57(9) 1_565 4_575 ?
N4 Zn1 O4 88.86(9) 1_565 4_575 ?
N4 Zn1 O5 86.95(9) 1_565 . ?
N4 Zn1 N1 179.05(10) 1_565 . ?
C8 O2 Zn1 127.6(2) . . ?
C10 O3 Zn1 89.25(17) . 4_676 ?
C10 O4 Zn1 90.39(16) . 4_676 ?
H5a O5 Zn1 109.4 . . ?
H5b O5 Zn1 109.4 . . ?
H5b O5 H5a 104.5 . . ?
C11 N1 Zn1 127.8(2) . . ?
C12 N1 Zn1 127.1(2) . . ?
C12 N1 C11 104.9(3) . . ?
C13 N2 C11 106.4(3) . . ?
C14 N2 C11 125.7(3) . . ?
C14 N2 C13 127.8(3) . . ?
C20 N3 C17 126.5(3) . . ?
C22 N3 C17 126.6(2) . . ?
C22 N3 C20 106.9(2) . . ?
C20 N4 Zn1 125.8(2) . 1_545 ?
C21 N4 Zn1 128.26(19) . 1_545 ?
C21 N4 C20 105.9(2) . . ?
C6 C1 C2 119.3(3) . . ?
C7 C1 C2 121.9(3) . . ?
C7 C1 C6 118.8(4) . . ?
C3 C2 C1 116.7(4) . . ?
C9 C2 C1 122.3(3) . . ?
C9 C2 C3 121.0(4) . . ?
C4 C3 C2 122.1(5) . . ?
H3 C3 C2 118.9(3) . . ?
H3 C3 C4 118.9(4) . . ?
C5 C4 C3 119.8(5) . . ?
H4 C4 C3 120.1(4) . . ?
H4 C4 C5 120.1(3) . . ?
C6 C5 C4 119.8(5) . . ?
H5 C5 C4 120.1(3) . . ?
H5 C5 C6 120.1(3) . . ?
C5 C6 C1 122.3(5) . . ?
H6 C6 C1 118.8(3) . . ?
H6 C6 C5 118.8(3) . . ?
C8 C7 C1 114.5(3) . . ?
H7a C7 C1 108.64(19) . . ?
H7a C7 C8 108.6(2) . . ?
H7b C7 C1 108.6(2) . . ?
H7b C7 C8 108.64(19) . . ?
H7b C7 H7a 107.6 . . ?
O2 C8 O1 125.2(3) . . ?
C7 C8 O1 117.2(3) . . ?
C7 C8 O2 117.6(3) . . ?
C10 C9 C2 116.0(3) . . ?
H9a C9 C2 108.3(2) . . ?
H9a C9 C10 108.3(2) . . ?
H9b C9 C2 108.3(2) . . ?
H9b C9 C10 108.29(18) . . ?
H9b C9 H9a 107.4 . . ?
O4 C10 O3 120.7(3) . . ?
C9 C10 O3 118.1(3) . . ?
C9 C10 O4 121.2(3) . . ?
N2 C11 N1 112.2(3) . . ?
H11 C11 N1 123.92(18) . . ?
H11 C11 N2 123.92(17) . . ?
C13 C12 N1 110.4(3) . . ?
H12 C12 N1 124.81(19) . . ?
H12 C12 C13 124.8(2) . . ?
C12 C13 N2 106.2(3) . . ?
H13 C13 N2 126.90(18) . . ?
H13 C13 C12 126.9(2) . . ?
C15 C14 N2 119.6(3) . . ?
C19 C14 N2 120.1(3) . . ?
C19 C14 C15 120.3(3) . . ?
C16 C15 C14 119.2(3) . . ?
H15 C15 C14 120.4(2) . . ?
H15 C15 C16 120.4(2) . . ?
C17 C16 C15 120.7(3) . . ?
H16 C16 C15 119.6(2) . . ?
H16 C16 C17 119.63(18) . . ?
C16 C17 N3 120.1(3) . . ?
C18 C17 N3 120.3(3) . . ?
C18 C17 C16 119.5(3) . . ?
C19 C18 C17 119.7(3) . . ?
H18 C18 C17 120.17(18) . . ?
H18 C18 C19 120.17(18) . . ?
C18 C19 C14 120.6(3) . . ?
H19 C19 C14 119.71(17) . . ?
H19 C19 C18 119.71(18) . . ?
N4 C20 N3 111.3(2) . . ?
H20 C20 N3 124.36(16) . . ?
H20 C20 N4 124.36(16) . . ?
C22 C21 N4 109.8(3) . . ?
H21 C21 N4 125.08(16) . . ?
H21 C21 C22 125.08(19) . . ?
C21 C22 N3 106.1(3) . . ?
H22 C22 N3 126.94(16) . . ?
H22 C22 C21 126.94(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
