# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 1946662'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N3 O4 Zn'
_chemical_formula_sum            'C20 H15 N3 O4 Zn'
_chemical_formula_weight         426.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3289(4)
_cell_length_b                   9.6117(4)
_cell_length_c                   14.9979(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.083(3)
_cell_angle_gamma                90
_cell_volume                     1763.71(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.4410
_cell_measurement_theta_min      3.6600
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.599
_exptl_absorpt_coefficient_mu    1.426
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10390
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.970
_diffrn_reflns_theta_min         2.928
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  25.00   1.00   28.00    --  -13.28 -99.00  30.00   31
  2  ω   -103.00 -77.00   1.00   28.00    --  -13.28-178.00  30.00   26
  3  ω    -19.00  17.00   1.00   28.00    --  -13.28 -99.00 -90.00   36
  4  ω     47.00  85.00   1.00   28.00    --   13.28 178.00-150.00   38
  5  ω    -61.00  38.00   1.00   28.00    --   13.28 -57.00   0.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0314661000
_diffrn_orient_matrix_UB_12      -0.0334285000
_diffrn_orient_matrix_UB_13      -0.0366511000
_diffrn_orient_matrix_UB_21      0.0272171000
_diffrn_orient_matrix_UB_22      0.0394557000
_diffrn_orient_matrix_UB_23      -0.0304750000
_diffrn_orient_matrix_UB_31      0.0403644000
_diffrn_orient_matrix_UB_32      -0.0526377000
_diffrn_orient_matrix_UB_33      0.0004361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3589
_reflns_number_total             4446
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0768
_refine_special_details          ?
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.50568(2) 0.68314(2) 0.26798(2) 0.01838(8) Uani 1 1 d . . . . .
O1 O 0.36629(11) 0.58660(15) 0.22076(9) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.64722(11) 0.58926(15) 0.30956(9) 0.0240(3) Uani 1 1 d . . . . .
O11 O 0.21543(12) 0.48921(17) 0.26082(10) 0.0326(4) Uani 1 1 d . . . . .
O22 O 0.78568(12) 0.47192(18) 0.26398(10) 0.0343(4) Uani 1 1 d . . . . .
N1 N 0.43753(12) 0.64476(17) 0.39158(10) 0.0179(3) Uani 1 1 d . . . . .
N2 N 0.57066(12) 0.65744(17) 0.14169(11) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.50418(15) 0.8931(2) 0.28090(14) 0.0249(4) Uani 1 1 d . . . . .
H3A H 0.445(2) 0.928(3) 0.2577(16) 0.036(7) Uiso 1 1 d . . . . .
H3B H 0.560(2) 0.929(3) 0.2594(16) 0.036(7) Uiso 1 1 d . . . . .
H3C H 0.512(2) 0.914(3) 0.339(2) 0.055(9) Uiso 1 1 d . . . . .
C10 C 0.47635(15) 0.68394(19) 0.47772(13) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.58473(17) 0.7332(2) 0.49703(14) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.6274(18) 0.733(2) 0.4513(15) 0.022(6) Uiso 1 1 d . . . . .
C12 C 0.62355(19) 0.7745(2) 0.58219(15) 0.0281(5) Uani 1 1 d . . . . .
H12 H 0.693(2) 0.810(2) 0.5949(15) 0.028(6) Uiso 1 1 d . . . . .
C13 C 0.5564(2) 0.7676(2) 0.65158(15) 0.0289(5) Uani 1 1 d . . . . .
H13 H 0.5847(19) 0.796(2) 0.7107(16) 0.028(6) Uiso 1 1 d . . . . .
C14 C 0.4529(2) 0.7186(2) 0.63496(14) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.404(2) 0.716(2) 0.6786(17) 0.034(7) Uiso 1 1 d . . . . .
C15 C 0.40880(17) 0.6759(2) 0.54748(13) 0.0215(4) Uani 1 1 d . . . . .
C16 C 0.30167(17) 0.6254(2) 0.52611(14) 0.0237(4) Uani 1 1 d . . . . .
H16 H 0.2560(18) 0.624(2) 0.5725(15) 0.025(6) Uiso 1 1 d . . . . .
C17 C 0.26593(16) 0.5846(2) 0.44042(14) 0.0227(4) Uani 1 1 d . . . . .
H17 H 0.2000(18) 0.554(2) 0.4251(13) 0.018(5) Uiso 1 1 d . . . . .
C18 C 0.33747(15) 0.5962(2) 0.37450(13) 0.0191(4) Uani 1 1 d . . . . .
C19 C 0.30188(15) 0.5528(2) 0.27744(13) 0.0209(4) Uani 1 1 d . . . . .
C20 C 0.52753(15) 0.6956(2) 0.05652(13) 0.0192(4) Uani 1 1 d . . . . .
C21 C 0.43429(17) 0.7824(2) 0.04418(14) 0.0242(4) Uani 1 1 d . . . . .
H21 H 0.4040(18) 0.811(2) 0.0949(15) 0.020(5) Uiso 1 1 d . . . . .
C22 C 0.39205(19) 0.8228(2) -0.04048(14) 0.0281(5) Uani 1 1 d . . . . .
H22 H 0.3298(19) 0.877(2) -0.0492(15) 0.029(6) Uiso 1 1 d . . . . .
C23 C 0.4401(2) 0.7774(2) -0.11600(15) 0.0296(5) Uani 1 1 d . . . . .
H23 H 0.409(2) 0.807(2) -0.1714(17) 0.034(7) Uiso 1 1 d . . . . .
C24 C 0.52806(18) 0.6918(2) -0.10622(14) 0.0263(5) Uani 1 1 d . . . . .
H24 H 0.5590(19) 0.657(2) -0.1548(16) 0.031(6) Uiso 1 1 d . . . . .
C25 C 0.57555(16) 0.6497(2) -0.01930(13) 0.0216(4) Uani 1 1 d . . . . .
C26 C 0.66889(17) 0.5637(2) -0.00488(14) 0.0251(4) Uani 1 1 d . . . . .
H26 H 0.6991(18) 0.530(2) -0.0561(14) 0.023(6) Uiso 1 1 d . . . . .
C27 C 0.71097(17) 0.5294(2) 0.08040(14) 0.0247(4) Uani 1 1 d . . . . .
H27 H 0.7687(18) 0.473(2) 0.0919(14) 0.023(6) Uiso 1 1 d . . . . .
C28 C 0.65904(15) 0.5789(2) 0.15269(13) 0.0197(4) Uani 1 1 d . . . . .
C29 C 0.70229(15) 0.5430(2) 0.24953(13) 0.0226(4) Uani 1 1 d . . . . .


_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 2.0039(13) . ?
Zn1 O2 1.9949(13) . ?
Zn1 N1 2.1593(15) . ?
Zn1 N2 2.1599(16) . ?
Zn1 N3 2.0281(19) . ?
O1 C19 1.275(2) . ?
O2 C29 1.273(2) . ?
O11 C19 1.227(2) . ?
O22 C29 1.231(2) . ?
N1 C10 1.374(2) . ?
N1 C18 1.314(2) . ?
N2 C20 1.372(2) . ?
N2 C28 1.319(2) . ?
C10 C11 1.414(3) . ?
C10 C15 1.417(3) . ?
C11 C12 1.367(3) . ?
C12 C13 1.409(3) . ?
C13 C14 1.355(3) . ?
C14 C15 1.418(3) . ?
C15 C16 1.406(3) . ?
C16 C17 1.364(3) . ?
C17 C18 1.408(3) . ?
C18 C19 1.526(3) . ?
C20 C21 1.414(3) . ?
C20 C25 1.416(3) . ?
C21 C22 1.368(3) . ?
C22 C23 1.410(3) . ?
C23 C24 1.355(3) . ?
C24 C25 1.421(3) . ?
C25 C26 1.412(3) . ?
C26 C27 1.360(3) . ?
C27 C28 1.408(3) . ?
C28 C29 1.524(3) . ?

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 79.44(6) . . ?
O1 Zn1 N2 91.82(6) . . ?
O1 Zn1 N3 118.50(7) . . ?
O2 Zn1 O1 125.45(6) . . ?
O2 Zn1 N1 94.15(6) . . ?
O2 Zn1 N2 79.49(6) . . ?
O2 Zn1 N3 115.99(7) . . ?
N1 Zn1 N2 163.54(6) . . ?
N3 Zn1 N1 94.53(7) . . ?
N3 Zn1 N2 101.91(7) . . ?
C19 O1 Zn1 117.38(12) . . ?
C29 O2 Zn1 117.34(12) . . ?
C10 N1 Zn1 129.29(12) . . ?
C18 N1 Zn1 110.39(12) . . ?
C18 N1 C10 119.37(16) . . ?
C20 N2 Zn1 130.02(12) . . ?
C28 N2 Zn1 110.23(13) . . ?
C28 N2 C20 119.26(16) . . ?
N1 C10 C11 119.70(17) . . ?
N1 C10 C15 120.72(17) . . ?
C11 C10 C15 119.58(18) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C13 120.5(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 121.1(2) . . ?
C10 C15 C14 118.31(19) . . ?
C16 C15 C10 118.13(18) . . ?
C16 C15 C14 123.57(19) . . ?
C17 C16 C15 119.94(18) . . ?
C16 C17 C18 118.76(19) . . ?
N1 C18 C17 123.06(18) . . ?
N1 C18 C19 115.83(16) . . ?
C17 C18 C19 121.11(17) . . ?
O1 C19 C18 115.91(16) . . ?
O11 C19 O1 126.03(19) . . ?
O11 C19 C18 118.06(17) . . ?
N2 C20 C21 119.68(17) . . ?
N2 C20 C25 120.81(17) . . ?
C21 C20 C25 119.52(18) . . ?
C22 C21 C20 119.95(19) . . ?
C21 C22 C23 120.6(2) . . ?
C24 C23 C22 120.7(2) . . ?
C23 C24 C25 120.4(2) . . ?
C20 C25 C24 118.83(18) . . ?
C26 C25 C20 118.25(18) . . ?
C26 C25 C24 122.92(19) . . ?
C27 C26 C25 119.68(19) . . ?
C26 C27 C28 119.03(19) . . ?
N2 C28 C27 122.96(18) . . ?
N2 C28 C29 115.80(17) . . ?
C27 C28 C29 121.24(17) . . ?
O2 C29 C28 116.15(17) . . ?
O22 C29 O2 125.18(19) . . ?
O22 C29 C28 118.67(18) . . ?

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
_geom_hbond_publ_flag
N3 H3A O11 0.84(3) 2.04(3) 2.856(2) 161(2) 2 yes
N3 H3B O22 0.86(3) 2.02(3) 2.858(2) 162(2) 2_655 yes

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1946666'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O5 Zn, H2 O'
_chemical_formula_sum            'C23 H23 N3 O6 Zn'
_chemical_formula_weight         502.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.8788(11)
_cell_length_b                   7.6223(6)
_cell_length_c                   18.3192(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.464(7)
_cell_angle_gamma                90
_cell_volume                     2147.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7230
_cell_measurement_theta_min      2.8790
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10235
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.707
_diffrn_reflns_theta_min         2.649
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -69.00   1.00  205.00    --  -12.36-178.00 -60.00   33
  2  ω    -96.00 -61.00   1.00  205.00    --  -12.36 178.00-150.00   35
  3  ω    -19.00   7.00   1.00  205.00    --   12.52 -99.00  30.00   26
  4  ω    -18.00  85.00   1.00  205.00    --   12.52  77.00-180.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0439859000
_diffrn_orient_matrix_UB_12      0.0273402000
_diffrn_orient_matrix_UB_13      0.0067269000
_diffrn_orient_matrix_UB_21      0.0132299000
_diffrn_orient_matrix_UB_22      -0.0745101000
_diffrn_orient_matrix_UB_23      0.0232075000
_diffrn_orient_matrix_UB_31      0.0044634000
_diffrn_orient_matrix_UB_32      -0.0485059000
_diffrn_orient_matrix_UB_33      -0.0318610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             5115
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.963
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5115
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.48664(3) 0.54740(8) 0.72673(2) 0.02099(15) Uani 1 1 d . . . . .
O1 O 0.36815(17) 0.4483(5) 0.68916(14) 0.0255(7) Uani 1 1 d . . . . .
O2 O 0.59700(18) 0.4243(4) 0.72299(15) 0.0273(8) Uani 1 1 d . . . . .
O3 O 0.3616(2) 0.8763(6) 0.8323(2) 0.0497(12) Uani 1 1 d . . . . .
O11 O 0.25831(19) 0.4132(5) 0.58670(16) 0.0331(9) Uani 1 1 d . . . . .
O22 O 0.6972(2) 0.2292(4) 0.77968(17) 0.0319(8) Uani 1 1 d . . . . .
N1 N 0.4609(2) 0.6192(5) 0.60976(17) 0.0191(8) Uani 1 1 d . . . . .
N2 N 0.5132(2) 0.3952(5) 0.83158(17) 0.0228(9) Uani 1 1 d . . . . .
N3 N 0.5058(3) 0.7851(6) 0.7779(2) 0.0250(9) Uani 1 1 d . . . . .
H3A H 0.487(3) 0.777(7) 0.815(3) 0.049(16) Uiso 1 1 d . . . . .
H3B H 0.558(3) 0.790(6) 0.789(2) 0.021(13) Uiso 1 1 d . . . . .
C10 C 0.5121(3) 0.7046(6) 0.5701(2) 0.0195(10) Uani 1 1 d . . . . .
C11 C 0.5950(3) 0.7649(6) 0.6085(2) 0.0238(10) Uani 1 1 d . . . . .
H11 H 0.615432 0.745402 0.660051 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6457(3) 0.8524(6) 0.5700(2) 0.0269(11) Uani 1 1 d . . . . .
H12 H 0.699998 0.894411 0.595726 0.032 Uiso 1 1 calc R . . . .
C13 C 0.6163(3) 0.8790(6) 0.4919(2) 0.0275(11) Uani 1 1 d . . . . .
H13 H 0.651657 0.937567 0.466356 0.033 Uiso 1 1 calc R . . . .
C14 C 0.5375(3) 0.8210(6) 0.4535(2) 0.0258(11) Uani 1 1 d . . . . .
H14 H 0.519501 0.838082 0.401637 0.031 Uiso 1 1 calc R . . . .
C15 C 0.4815(3) 0.7337(6) 0.4915(2) 0.0197(10) Uani 1 1 d . . . . .
C16 C 0.3977(3) 0.6761(6) 0.4549(2) 0.0238(10) Uani 1 1 d . . . . .
H16 H 0.376490 0.693213 0.403275 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3474(3) 0.5947(6) 0.4952(2) 0.0231(10) Uani 1 1 d . . . . .
H17 H 0.291051 0.558826 0.472056 0.028 Uiso 1 1 calc R . . . .
C18 C 0.3828(3) 0.5665(6) 0.5726(2) 0.0202(9) Uani 1 1 d . . . . .
C19 C 0.3310(3) 0.4674(6) 0.6193(2) 0.0226(10) Uani 1 1 d . . . . .
C20 C 0.4672(3) 0.3777(7) 0.8859(2) 0.0246(10) Uani 1 1 d . . . . .
C21 C 0.3872(3) 0.4688(7) 0.8757(2) 0.0294(11) Uani 1 1 d . . . . .
H21 H 0.366656 0.539498 0.833652 0.035 Uiso 1 1 calc R . . . .
C22 C 0.3408(3) 0.4507(8) 0.9289(2) 0.0369(12) Uani 1 1 d . . . . .
H22 H 0.288225 0.509659 0.922622 0.044 Uiso 1 1 calc R . . . .
C23 C 0.3710(3) 0.3452(8) 0.9927(2) 0.0377(14) Uani 1 1 d . . . . .
H23 H 0.337784 0.333958 1.027723 0.045 Uiso 1 1 calc R . . . .
C24 C 0.4472(3) 0.2599(7) 1.0039(2) 0.0345(12) Uani 1 1 d . . . . .
H24 H 0.466483 0.191149 1.046781 0.041 Uiso 1 1 calc R . . . .
C25 C 0.4988(3) 0.2739(7) 0.9507(2) 0.0264(11) Uani 1 1 d . . . . .
C26 C 0.5794(3) 0.1919(6) 0.9600(2) 0.0297(11) Uani 1 1 d . . . . .
H26 H 0.602676 0.126975 1.003326 0.036 Uiso 1 1 calc R . . . .
C27 C 0.6242(3) 0.2069(6) 0.9055(2) 0.0284(11) Uani 1 1 d . . . . .
H27 H 0.677377 0.150691 0.910702 0.034 Uiso 1 1 calc R . . . .
C28 C 0.5882(3) 0.3085(6) 0.8419(2) 0.0213(10) Uani 1 1 d . . . . .
C29 C 0.6315(3) 0.3220(7) 0.7764(2) 0.0249(10) Uani 1 1 d . . . . .
C31 C 0.4751(3) 0.9448(7) 0.7330(2) 0.0273(10) Uani 1 1 d . . . . .
H31A H 0.496529 0.943384 0.687863 0.033 Uiso 1 1 calc R . . . .
H31B H 0.498942 1.047454 0.762190 0.033 Uiso 1 1 calc R . . . .
C32 C 0.3769(3) 0.9585(7) 0.7107(2) 0.0307(11) Uani 1 1 d . . . . .
H32A H 0.360145 1.046943 0.671665 0.037 Uiso 1 1 calc R . . . .
H32B H 0.352977 0.847283 0.689387 0.037 Uiso 1 1 calc R . . . .
C33 C 0.3376(3) 1.0049(7) 0.7750(3) 0.0339(13) Uani 1 1 d . . . . .
H33A H 0.358243 1.119200 0.794994 0.041 Uiso 1 1 calc R . . . .
H33B H 0.274773 1.009871 0.757256 0.041 Uiso 1 1 calc R . . . .
O4 O 0.8037(2) 0.3609(6) 0.6864(2) 0.0346(9) Uani 1 1 d D . . . .
H4A H 0.773(4) 0.305(7) 0.709(3) 0.051(18) Uiso 1 1 d . . . . .
H4B H 0.805(5) 0.464(3) 0.697(4) 0.09(3) Uiso 1 1 d D . . . .
H3 H 0.330(4) 0.876(8) 0.857(3) 0.07(2) Uiso 1 1 d . . . . .


_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 1.984(3) . ?
Zn1 O2 2.004(3) . ?
Zn1 N1 2.150(3) . ?
Zn1 N2 2.193(3) . ?
Zn1 N3 2.028(4) . ?
O1 C19 1.276(5) . ?
O2 C29 1.264(5) . ?
O3 C33 1.417(6) . ?
O11 C19 1.231(5) . ?
O22 C29 1.250(5) . ?
N1 C10 1.381(5) . ?
N1 C18 1.320(5) . ?
N2 C20 1.380(5) . ?
N2 C28 1.334(5) . ?
N3 C31 1.482(6) . ?
C10 C11 1.406(6) . ?
C10 C15 1.419(5) . ?
C11 C12 1.369(6) . ?
C12 C13 1.405(6) . ?
C13 C14 1.348(6) . ?
C14 C15 1.423(6) . ?
C15 C16 1.402(6) . ?
C16 C17 1.366(6) . ?
C17 C18 1.405(5) . ?
C18 C19 1.528(6) . ?
C20 C21 1.418(6) . ?
C20 C25 1.411(6) . ?
C21 C22 1.367(5) . ?
C22 C23 1.401(7) . ?
C23 C24 1.344(7) . ?
C24 C25 1.425(6) . ?
C25 C26 1.396(6) . ?
C26 C27 1.367(6) . ?
C27 C28 1.398(6) . ?
C28 C29 1.527(5) . ?
C31 C32 1.513(6) . ?
C32 C33 1.507(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
O1 Zn1 O2 124.85(13) . . ?
O1 Zn1 N1 79.84(12) . . ?
O1 Zn1 N2 93.48(12) . . ?
O1 Zn1 N3 121.36(15) . . ?
O2 Zn1 N1 92.01(12) . . ?
O2 Zn1 N2 78.68(12) . . ?
O2 Zn1 N3 113.74(14) . . ?
N1 Zn1 N2 162.73(14) . . ?
N3 Zn1 N1 101.69(15) . . ?
N3 Zn1 N2 95.39(15) . . ?
C19 O1 Zn1 117.7(2) . . ?
C29 O2 Zn1 118.4(2) . . ?
C10 N1 Zn1 130.9(3) . . ?
C18 N1 Zn1 110.9(2) . . ?
C18 N1 C10 118.2(3) . . ?
C20 N2 Zn1 131.4(3) . . ?
C28 N2 Zn1 110.8(2) . . ?
C28 N2 C20 117.8(4) . . ?
C31 N3 Zn1 119.1(3) . . ?
N1 C10 C11 119.4(3) . . ?
N1 C10 C15 120.7(4) . . ?
C11 C10 C15 119.9(4) . . ?
C12 C11 C10 119.9(4) . . ?
C11 C12 C13 120.5(4) . . ?
C14 C13 C12 120.9(4) . . ?
C13 C14 C15 120.6(4) . . ?
C10 C15 C14 118.2(4) . . ?
C16 C15 C10 118.7(4) . . ?
C16 C15 C14 123.1(4) . . ?
C17 C16 C15 119.8(4) . . ?
C16 C17 C18 118.3(4) . . ?
N1 C18 C17 124.2(4) . . ?
N1 C18 C19 115.5(3) . . ?
C17 C18 C19 120.3(4) . . ?
O1 C19 C18 116.1(4) . . ?
O11 C19 O1 126.3(4) . . ?
O11 C19 C18 117.7(4) . . ?
N2 C20 C21 118.5(4) . . ?
N2 C20 C25 121.3(4) . . ?
C25 C20 C21 120.2(4) . . ?
C22 C21 C20 118.8(4) . . ?
C21 C22 C23 121.3(5) . . ?
C24 C23 C22 120.8(4) . . ?
C23 C24 C25 120.6(4) . . ?
C20 C25 C24 118.2(4) . . ?
C26 C25 C20 118.4(4) . . ?
C26 C25 C24 123.3(4) . . ?
C27 C26 C25 120.1(4) . . ?
C26 C27 C28 118.4(4) . . ?
N2 C28 C27 123.8(4) . . ?
N2 C28 C29 114.6(4) . . ?
C27 C28 C29 121.5(4) . . ?
O2 C29 C28 117.2(4) . . ?
O22 C29 O2 125.5(4) . . ?
O22 C29 C28 117.3(4) . . ?
N3 C31 C32 112.4(4) . . ?
C33 C32 C31 113.9(4) . . ?
O3 C33 C32 109.3(4) . . ?

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
_geom_hbond_publ_flag
N3 H3A O3 0.82(5) 2.22(5) 2.804(5) 129(5) . yes
N3 H3B O4 0.80(5) 2.20(5) 2.987(5) 168(5) 2_656 yes
O4 H4A O22 0.83(5) 2.06(5) 2.868(5) 164(5) . yes
O4 H4B O22 0.81(2) 2.07(2) 2.876(6) 178(8) 2_656 yes
O3 H3 O11 0.75(6) 1.96(6) 2.704(4) 171(7) 2_556 yes

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1946667'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O5 Zn'
_chemical_formula_sum            'C23 H21 N3 O5 Zn'
_chemical_formula_weight         484.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.156(3)
_cell_length_b                   7.8984(7)
_cell_length_c                   14.1312(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.031(12)
_cell_angle_gamma                90
_cell_volume                     2033.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1606
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.3720
_cell_measurement_theta_min      3.0030
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4781
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.530
_diffrn_reflns_theta_min         2.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2466
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  16.00   1.00  135.00    --  -12.44 -99.00  90.00   33
  2  ω   -100.00 -58.00   1.00  135.00    --  -12.44-178.00 -90.00   42
  3  ω    -26.00  93.00   1.00  135.00    --   12.52   0.00-120.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0200419000
_diffrn_orient_matrix_UB_12      -0.0767986000
_diffrn_orient_matrix_UB_13      -0.0075156000
_diffrn_orient_matrix_UB_21      0.0300145000
_diffrn_orient_matrix_UB_22      -0.0412033000
_diffrn_orient_matrix_UB_23      0.0349091000
_diffrn_orient_matrix_UB_31      -0.0145604000
_diffrn_orient_matrix_UB_32      0.0220301000
_diffrn_orient_matrix_UB_33      0.0388182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1847
_reflns_number_total             2447
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+2.8033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 0.36119(14) 0.8127(4) 0.62593(19) 0.0346(6) Uani 1 1 d . . . . .
C11 C 0.32716(15) 0.7861(4) 0.7004(2) 0.0435(7) Uani 1 1 d . . . . .
H11 H 0.349556 0.717576 0.754837 0.052 Uiso 1 1 calc R . . . .
C12 C 0.26117(16) 0.8615(5) 0.6920(2) 0.0490(8) Uani 1 1 d . . . . .
H12 H 0.239563 0.844050 0.741794 0.059 Uiso 1 1 calc R . . . .
C13 C 0.22545(17) 0.9635(5) 0.6111(2) 0.0543(9) Uani 1 1 d . . . . .
H13 H 0.180616 1.013326 0.607016 0.065 Uiso 1 1 calc R . . . .
C14 C 0.25695(16) 0.9897(5) 0.5378(2) 0.0515(8) Uani 1 1 d . . . . .
H14 H 0.233180 1.057472 0.483635 0.062 Uiso 1 1 calc R . . . .
C15 C 0.32494(15) 0.9154(4) 0.5432(2) 0.0427(7) Uani 1 1 d . . . . .
C16 C 0.35977(17) 0.9408(4) 0.4699(2) 0.0500(8) Uani 1 1 d . . . . .
H16 H 0.338368 1.010224 0.415478 0.060 Uiso 1 1 calc R . . . .
C17 C 0.42469(16) 0.8632(4) 0.4793(2) 0.0466(8) Uani 1 1 d . . . . .
H17 H 0.447700 0.878214 0.430795 0.056 Uiso 1 1 calc R . . . .
C18 C 0.45710(14) 0.7606(4) 0.56196(18) 0.0353(6) Uani 1 1 d . . . . .
C19 C 0.52881(15) 0.6698(4) 0.57200(19) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.42744(11) 0.7367(3) 0.63450(15) 0.0332(5) Uani 1 1 d . . . . .
O1 O 0.55363(11) 0.5766(2) 0.64695(15) 0.0422(5) Uani 1 1 d . . . . .
O11 O 0.55881(10) 0.6946(3) 0.50731(13) 0.0474(6) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.56681(6) 0.750000 0.04435(19) Uani 1 2 d S T P . .
N2 N 0.5361(2) 0.3285(5) 0.7945(3) 0.0271(9) Uani 0.5 1 d D U . A -1
C21 C 0.4890(6) 0.1889(6) 0.746(2) 0.0342(18) Uani 0.5 1 d . U . A -1
H21A H 0.496335 0.093298 0.791128 0.041 Uiso 0.5 1 calc R . . A -1
H21B H 0.501604 0.153590 0.687592 0.041 Uiso 0.5 1 calc R . . A -1
C22 C 0.4100(4) 0.2433(10) 0.7160(8) 0.0349(17) Uani 0.5 1 d . U . A -1
H22A H 0.378907 0.152037 0.680455 0.042 Uiso 0.5 1 calc R . . A -1
H22B H 0.396130 0.268874 0.774896 0.042 Uiso 0.5 1 calc R . . A -1
C23 C 0.6119(4) 0.3009(11) 0.7929(8) 0.0370(19) Uani 0.5 1 d . U . A -1
H23A H 0.628314 0.190778 0.819291 0.055 Uiso 0.5 1 calc GR . . A -1
H23B H 0.643546 0.385723 0.832678 0.055 Uiso 0.5 1 calc GR . . A -1
H23C H 0.613168 0.308141 0.725627 0.055 Uiso 0.5 1 calc GR . . A -1
O2 O 0.3997(2) 0.3895(5) 0.6538(3) 0.0303(8) Uani 0.5 1 d . . . A -1
H2 H 0.539(3) 0.329(6) 0.8571(17) 0.018(12) Uiso 0.5 1 d D . . B -1
H2A H 0.407(3) 0.364(7) 0.605(4) 0.025(14) Uiso 0.5 1 d . . . C -1


_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
C10 C11 1.414(4) . ?
C10 C15 1.416(4) . ?
C10 N1 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(4) . ?
C15 C16 1.409(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(4) . ?
C18 C19 1.517(4) . ?
C18 N1 1.330(3) . ?
C19 O1 1.256(3) . ?
C19 O11 1.237(3) . ?
N1 Zn1 2.234(2) . ?
O1 Zn1 2.0269(16) . ?
Zn1 N2 2.036(4) . ?
Zn1 O2 2.425(4) . ?
N2 C21 1.456(12) . ?
N2 C23 1.476(8) . ?
N2 H2 0.870(19) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(14) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 O2 1.427(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 H2A 0.78(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
C11 C10 C15 118.6(3) . . ?
N1 C10 C11 119.7(3) . . ?
N1 C10 C15 121.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.9(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 119.5(3) . . ?
C14 C15 C16 122.8(3) . . ?
C16 C15 C10 117.8(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.4(2) . . ?
N1 C18 C17 122.7(3) . . ?
N1 C18 C19 116.8(2) . . ?
O1 C19 C18 116.8(2) . . ?
O11 C19 C18 118.1(3) . . ?
O11 C19 O1 125.1(3) . . ?
C10 N1 Zn1 132.45(17) . . ?
C18 N1 C10 118.2(2) . . ?
C18 N1 Zn1 109.30(18) . . ?
C19 O1 Zn1 118.98(17) . . ?
N1 Zn1 N1 106.17(11) 2_656 . ?
N1 Zn1 O2 74.44(10) . . ?
N1 Zn1 O2 164.12(10) 2_656 . ?
O1 Zn1 N1 77.95(8) . . ?
O1 Zn1 N1 99.37(8) . 2_656 ?
O1 Zn1 N1 99.37(8) 2_656 . ?
O1 Zn1 N1 77.95(8) 2_656 2_656 ?
O1 Zn1 O1 175.62(11) 2_656 . ?
O1 Zn1 N2 90.71(11) 2_656 . ?
O1 Zn1 N2 93.34(11) . . ?
O1 Zn1 O2 86.26(11) 2_656 . ?
O1 Zn1 O2 96.28(11) . . ?
N2 Zn1 N1 104.73(13) . 2_656 ?
N2 Zn1 N1 148.85(13) . . ?
N2 Zn1 O2 76.93(15) . . ?
Zn1 N2 H2 103(3) . . ?
C21 N2 Zn1 116.9(6) . . ?
C21 N2 C23 110.5(7) . . ?
C21 N2 H2 108(4) . . ?
C23 N2 Zn1 111.9(4) . . ?
C23 N2 H2 106(3) . . ?
N2 C21 H21A 109.7 . . ?
N2 C21 H21B 109.7 . . ?
N2 C21 C22 109.9(6) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O2 C22 C21 109.9(9) . . ?
O2 C22 H22A 109.7 . . ?
O2 C22 H22B 109.7 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Zn1 O2 H2A 108(4) . . ?
C22 O2 Zn1 100.8(4) . . ?
C22 O2 H2A 108(4) . . ?

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
_geom_hbond_publ_flag
N2 H2 O11 0.870(19) 2.05(2) 2.907(4) 171(5) 6_566 yes
O2 H2A O11 0.78(5) 1.94(5) 2.717(4) 172(6) 5_666 yes

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
C10 C11 C12 C13 0.7(5) . . . . ?
C10 C15 C16 C17 2.0(4) . . . . ?
C11 C10 C15 C14 0.8(4) . . . . ?
C11 C10 C15 C16 179.8(3) . . . . ?
C11 C10 N1 C18 178.3(2) . . . . ?
C11 C10 N1 Zn1 -0.3(4) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C17 -179.1(3) . . . . ?
C15 C10 C11 C12 -1.1(4) . . . . ?
C15 C10 N1 C18 -0.6(4) . . . . ?
C15 C10 N1 Zn1 -179.20(19) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C19 178.5(3) . . . . ?
C16 C17 C18 N1 -1.2(5) . . . . ?
C17 C18 C19 O1 -178.3(3) . . . . ?
C17 C18 C19 O11 2.8(4) . . . . ?
C17 C18 N1 C10 1.9(4) . . . . ?
C17 C18 N1 Zn1 -179.2(2) . . . . ?
C18 C19 O1 Zn1 -3.5(3) . . . . ?
C19 C18 N1 C10 -177.8(2) . . . . ?
C19 C18 N1 Zn1 1.1(3) . . . . ?
N1 C10 C11 C12 -180.0(3) . . . . ?
N1 C10 C15 C14 179.7(3) . . . . ?
N1 C10 C15 C16 -1.3(4) . . . . ?
N1 C18 C19 O1 1.4(4) . . . . ?
N1 C18 C19 O11 -177.5(2) . . . . ?
O11 C19 O1 Zn1 175.3(2) . . . . ?
Zn1 N2 C21 C22 -31(2) . . . . ?
N2 C21 C22 O2 56.2(19) . . . . ?
C21 C22 O2 Zn1 -48.6(11) . . . . ?
C23 N2 C21 C22 -160.2(14) . . . . ?

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1946663'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O5 Zn, C2 H3 N'
_chemical_formula_sum            'C25 H24 N4 O5 Zn'
_chemical_formula_weight         525.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8724(2)
_cell_length_b                   11.3651(5)
_cell_length_c                   14.9498(5)
_cell_angle_alpha                68.924(4)
_cell_angle_beta                 84.619(3)
_cell_angle_gamma                71.212(4)
_cell_volume                     1181.22(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.8430
_cell_measurement_theta_min      3.4520
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13581
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.331
_diffrn_reflns_theta_min         2.851
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  54.00   1.00    5.00    --  -14.04  19.00 -90.00  107
  2  ω     16.00  42.00   1.00    5.00    --   14.04 -57.00-120.00   26
  3  ω    -20.00  27.00   1.00    5.00    --  -14.04 -99.00-120.00   47
  4  ω    -11.00  89.00   1.00    5.00    --   14.04  37.00-180.00  100
  5  ω     12.00  39.00   1.00    5.00    --   14.04 -77.00  30.00   27
  6  ω    -19.00  54.00   1.00    5.00    --   14.04 -99.00  30.00   73
  7  ω     49.00  74.00   1.00    5.00    --   14.04-178.00   0.00   25
  8  ω     54.00  79.00   1.00    5.00    --   14.04 178.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0341124000
_diffrn_orient_matrix_UB_12      0.0648083000
_diffrn_orient_matrix_UB_13      0.0020820000
_diffrn_orient_matrix_UB_21      0.0082596000
_diffrn_orient_matrix_UB_22      0.0273730000
_diffrn_orient_matrix_UB_23      -0.0503541000
_diffrn_orient_matrix_UB_31      -0.0884938000
_diffrn_orient_matrix_UB_32      0.0010670000
_diffrn_orient_matrix_UB_33      -0.0068683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5107
_reflns_number_total             6173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.5190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.31955(3) 0.39335(2) 0.29446(2) 0.02085(8) Uani 1 1 d . . . . .
O1 O 0.26252(19) 0.30615(15) 0.21197(10) 0.0277(3) Uani 1 1 d . . . . .
O2 O 0.56157(17) 0.37154(14) 0.34365(10) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.1779(2) 0.57409(17) 0.49705(12) 0.0371(4) Uani 1 1 d . . . . .
H3 H 0.186(3) 0.568(3) 0.5521(19) 0.033(7) Uiso 1 1 d . . . . .
O11 O 0.2006(2) 0.12765(16) 0.21290(12) 0.0396(4) Uani 1 1 d . . . . .
O22 O 0.7894(2) 0.45466(17) 0.31356(11) 0.0354(4) Uani 1 1 d . . . . .
N1 N 0.2886(2) 0.21450(16) 0.40339(12) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.4174(2) 0.52357(16) 0.16963(11) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.1080(2) 0.52822(18) 0.32997(13) 0.0222(3) Uani 1 1 d . . . . .
H3A H 0.105(3) 0.508(2) 0.3924(18) 0.027(6) Uiso 1 1 d . . . . .
H3B H 0.014(3) 0.519(3) 0.3119(18) 0.039(7) Uiso 1 1 d . . . . .
C10 C 0.3067(2) 0.16915(19) 0.50156(13) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.3471(3) 0.2476(2) 0.54633(15) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.358(3) 0.332(2) 0.5092(17) 0.031(6) Uiso 1 1 d . . . . .
C12 C 0.3664(3) 0.2024(2) 0.64418(15) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.388(3) 0.259(3) 0.6715(18) 0.036(7) Uiso 1 1 d . . . . .
C13 C 0.3488(3) 0.0778(2) 0.70098(16) 0.0321(5) Uani 1 1 d . . . . .
H13 H 0.372(3) 0.046(2) 0.7701(18) 0.035(6) Uiso 1 1 d . . . . .
C14 C 0.3103(3) 0.0007(2) 0.65914(16) 0.0294(5) Uani 1 1 d . . . . .
H14 H 0.304(3) -0.083(3) 0.6964(18) 0.033(6) Uiso 1 1 d . . . . .
C15 C 0.2864(2) 0.0443(2) 0.55841(15) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.2432(3) -0.0307(2) 0.51197(16) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.230(3) -0.113(3) 0.5481(18) 0.037(7) Uiso 1 1 d . . . . .
C17 C 0.2221(3) 0.0179(2) 0.41448(16) 0.0261(4) Uani 1 1 d . . . . .
H17 H 0.194(3) -0.027(3) 0.3814(18) 0.036(7) Uiso 1 1 d . . . . .
C18 C 0.2483(2) 0.1406(2) 0.36260(14) 0.0220(4) Uani 1 1 d . . . . .
C19 C 0.2347(3) 0.1943(2) 0.25328(15) 0.0257(4) Uani 1 1 d . . . . .
C20 C 0.3425(2) 0.59484(19) 0.07920(14) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.1730(3) 0.5917(2) 0.05768(16) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.116(3) 0.538(2) 0.1050(17) 0.031(6) Uiso 1 1 d . . . . .
C22 C 0.0973(3) 0.6634(2) -0.03204(16) 0.0324(5) Uani 1 1 d . . . . .
H22 H -0.012(3) 0.657(2) -0.0460(17) 0.036(7) Uiso 1 1 d . . . . .
C23 C 0.1856(3) 0.7405(2) -0.10387(16) 0.0351(5) Uani 1 1 d . . . . .
H23 H 0.131(3) 0.792(2) -0.1670(18) 0.035(7) Uiso 1 1 d . . . . .
C24 C 0.3490(3) 0.7442(2) -0.08535(16) 0.0321(5) Uani 1 1 d . . . . .
H24 H 0.409(3) 0.794(3) -0.1322(18) 0.039(7) Uiso 1 1 d . . . . .
C25 C 0.4321(3) 0.6717(2) 0.00678(14) 0.0251(4) Uani 1 1 d . . . . .
C26 C 0.5992(3) 0.6744(2) 0.03088(16) 0.0330(5) Uani 1 1 d . . . . .
H26 H 0.653(3) 0.724(3) -0.0147(19) 0.044(7) Uiso 1 1 d . . . . .
C27 C 0.6695(3) 0.6046(2) 0.12127(16) 0.0306(5) Uani 1 1 d . . . . .
H27 H 0.776(3) 0.604(3) 0.1405(18) 0.039(7) Uiso 1 1 d . . . . .
C28 C 0.5750(2) 0.5285(2) 0.18862(14) 0.0216(4) Uani 1 1 d . . . . .
C29 C 0.6494(2) 0.4451(2) 0.29007(14) 0.0233(4) Uani 1 1 d . . . . .
C31 C 0.0983(3) 0.6705(2) 0.28951(16) 0.0264(4) Uani 1 1 d . . . . .
H31A H -0.024(3) 0.725(2) 0.2968(16) 0.025(6) Uiso 1 1 d . . . . .
H31B H 0.120(3) 0.691(2) 0.2210(17) 0.024(6) Uiso 1 1 d . . . . .
C32 C 0.2366(3) 0.6979(2) 0.33673(16) 0.0263(4) Uani 1 1 d . . . . .
H32A H 0.356(3) 0.628(2) 0.3414(16) 0.030(6) Uiso 1 1 d . . . . .
H32B H 0.245(3) 0.783(3) 0.2979(18) 0.039(7) Uiso 1 1 d . . . . .
C33 C 0.1908(3) 0.7001(2) 0.43705(16) 0.0279(4) Uani 1 1 d . . . . .
H33A H 0.281(3) 0.722(2) 0.4593(16) 0.027(6) Uiso 1 1 d . . . . .
H33B H 0.074(3) 0.768(3) 0.4362(17) 0.036(7) Uiso 1 1 d . . . . .
N4 N 0.2339(6) 0.1086(3) -0.0823(2) 0.0921(11) Uani 1 1 d . . . . .
C41 C 0.2342(5) 0.0368(3) -0.0064(2) 0.0634(9) Uani 1 1 d . . . . .
C42 C 0.2337(6) -0.0533(3) 0.0906(2) 0.0736(11) Uani 1 1 d . . . . .
H42A H 0.145704 -0.097095 0.095106 0.110 Uiso 1 1 calc GR . . . .
H42B H 0.204870 -0.004529 0.133647 0.110 Uiso 1 1 calc GR . . . .
H42C H 0.350153 -0.118099 0.107386 0.110 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9935(14) . ?
Zn1 O2 2.0149(13) . ?
Zn1 N1 2.1695(16) . ?
Zn1 N2 2.1785(15) . ?
Zn1 N3 2.0445(17) . ?
O1 C19 1.278(2) . ?
O2 C29 1.267(2) . ?
O3 C33 1.420(3) . ?
O11 C19 1.225(3) . ?
O22 C29 1.236(2) . ?
N1 C10 1.374(2) . ?
N1 C18 1.324(2) . ?
N2 C20 1.373(2) . ?
N2 C28 1.320(2) . ?
N3 C31 1.488(3) . ?
C10 C11 1.412(3) . ?
C10 C15 1.419(3) . ?
C11 C12 1.370(3) . ?
C12 C13 1.409(3) . ?
C13 C14 1.361(3) . ?
C14 C15 1.416(3) . ?
C15 C16 1.407(3) . ?
C16 C17 1.365(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.526(3) . ?
C20 C21 1.415(3) . ?
C20 C25 1.416(3) . ?
C21 C22 1.367(3) . ?
C22 C23 1.407(3) . ?
C23 C24 1.358(3) . ?
C24 C25 1.418(3) . ?
C25 C26 1.409(3) . ?
C26 C27 1.360(3) . ?
C27 C28 1.401(3) . ?
C28 C29 1.522(3) . ?
C31 C32 1.517(3) . ?
C32 C33 1.516(3) . ?
N4 C41 1.135(4) . ?
C41 C42 1.443(4) . ?

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 O2 128.35(6) . . ?
O1 Zn1 N1 79.77(6) . . ?
O1 Zn1 N2 89.64(6) . . ?
O1 Zn1 N3 116.44(7) . . ?
O2 Zn1 N1 95.24(6) . . ?
O2 Zn1 N2 78.79(6) . . ?
O2 Zn1 N3 115.16(7) . . ?
N1 Zn1 N2 160.85(6) . . ?
N3 Zn1 N1 98.19(6) . . ?
N3 Zn1 N2 100.81(6) . . ?
C19 O1 Zn1 117.91(13) . . ?
C29 O2 Zn1 117.42(12) . . ?
C10 N1 Zn1 131.21(13) . . ?
C18 N1 Zn1 110.03(13) . . ?
C18 N1 C10 118.75(16) . . ?
C20 N2 Zn1 130.14(12) . . ?
C28 N2 Zn1 110.99(13) . . ?
C28 N2 C20 118.86(16) . . ?
C31 N3 Zn1 118.38(13) . . ?
N1 C10 C11 119.49(17) . . ?
N1 C10 C15 120.87(18) . . ?
C11 C10 C15 119.64(18) . . ?
C12 C11 C10 119.7(2) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 120.8(2) . . ?
C14 C15 C10 118.71(19) . . ?
C16 C15 C10 118.39(18) . . ?
C16 C15 C14 122.90(19) . . ?
C17 C16 C15 119.58(19) . . ?
C16 C17 C18 119.0(2) . . ?
N1 C18 C17 123.39(19) . . ?
N1 C18 C19 116.41(17) . . ?
C17 C18 C19 120.19(18) . . ?
O1 C19 C18 115.88(17) . . ?
O11 C19 O1 125.8(2) . . ?
O11 C19 C18 118.29(19) . . ?
N2 C20 C21 119.69(17) . . ?
N2 C20 C25 121.04(17) . . ?
C21 C20 C25 119.27(18) . . ?
C22 C21 C20 119.8(2) . . ?
C21 C22 C23 121.0(2) . . ?
C24 C23 C22 120.4(2) . . ?
C23 C24 C25 120.5(2) . . ?
C20 C25 C24 119.06(18) . . ?
C26 C25 C20 117.90(19) . . ?
C26 C25 C24 123.03(19) . . ?
C27 C26 C25 119.98(19) . . ?
C26 C27 C28 118.9(2) . . ?
N2 C28 C27 123.26(19) . . ?
N2 C28 C29 115.40(16) . . ?
C27 C28 C29 121.34(17) . . ?
O2 C29 C28 116.89(16) . . ?
O22 C29 O2 125.38(19) . . ?
O22 C29 C28 117.73(17) . . ?
N3 C31 C32 111.57(17) . . ?
C33 C32 C31 114.38(17) . . ?
O3 C33 C32 109.08(18) . . ?
N4 C41 C42 179.4(4) . . ?

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
_geom_hbond_publ_flag
O3 H3 O22 0.81(3) 1.95(3) 2.758(2) 177(3) 2_666 yes
N3 H3A O3 0.88(2) 2.16(2) 2.862(2) 137(2) . yes
N3 H3B O22 0.86(3) 2.12(3) 2.943(2) 161(2) 1_455 yes

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1946665'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O5 Zn, C3 H8 O'
_chemical_formula_sum            'C26 H29 N3 O6 Zn'
_chemical_formula_weight         544.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9175(5)
_cell_length_b                   11.4683(6)
_cell_length_c                   15.3238(9)
_cell_angle_alpha                71.090(5)
_cell_angle_beta                 85.805(5)
_cell_angle_gamma                70.921(5)
_cell_volume                     1243.17(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5510
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.7330
_cell_measurement_theta_min      4.2770
_shelx_estimated_absorpt_T_max   0.719
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8490
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.993
_diffrn_reflns_theta_min         3.050
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -57.00   1.00    1.00    --  -41.63 125.00  30.00   28
  2  ω   -119.00 -13.00   1.00    1.00    --  -41.63 -19.00 -60.00  106
  3  ω    -50.00 -10.00   1.00    1.00    --  -41.63 125.00  30.00   40
  4  ω   -116.00 -46.00   1.00    1.00    --  -41.63 -37.00-120.00   70
  5  ω     28.00  90.00   1.00    1.00    --   41.63-125.00-150.00   62
  6  ω     89.00 116.00   1.00    1.00    --   41.63 165.00  63.00   27
  7  ω     31.00 100.00   1.00    4.00    --  104.43 -94.00-150.00   69
  8  ω     41.00 125.00   1.00    4.00    --  104.43 -45.00-150.00   84
  9  ω     79.00 178.00   1.00    4.00    --  104.43  30.00 -90.00   99
 10  ω     87.00 133.00   1.00    4.00    --  104.43 -61.00  30.00   46
 11  ω    105.00 175.00   1.00    4.00    --  104.43 125.00-150.00   70
 12  ω     32.00 117.00   1.00    4.00    --  104.43-125.00  60.00   85
 13  ω     54.00 113.00   1.00    4.00    --  104.43-116.00-171.00   59
 14  ω    108.00 165.00   1.00    4.00    --  104.43 125.00-180.00   57
 15  ω     38.00  75.00   1.00    4.00    --  104.43 -45.00 -60.00   37
 16  ω     61.00  96.00   1.00    4.00    --  104.43 -94.00 -60.00   35
 17  ω     24.00 129.00   1.00    4.00    --  104.43 -15.00  90.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1688961000
_diffrn_orient_matrix_UB_12      0.0589538000
_diffrn_orient_matrix_UB_13      -0.0638163000
_diffrn_orient_matrix_UB_21      0.1124072000
_diffrn_orient_matrix_UB_22      0.0421332000
_diffrn_orient_matrix_UB_23      -0.0834008000
_diffrn_orient_matrix_UB_31      0.0358456000
_diffrn_orient_matrix_UB_32      -0.1312765000
_diffrn_orient_matrix_UB_33      -0.0167421000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4604
_reflns_number_total             4795
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.6059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.68732(3) 0.62145(2) 0.69015(2) 0.01894(8) Uani 1 1 d . . . . .
O1 O 0.75922(17) 0.71283(12) 0.76434(8) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.44686(15) 0.64399(12) 0.63964(8) 0.0245(2) Uani 1 1 d . . . . .
O3 O 0.8345(2) 0.42093(15) 0.50614(10) 0.0423(4) Uani 1 1 d . . . . .
H3 H 0.816(4) 0.425(3) 0.455(2) 0.047(7) Uiso 1 1 d . . . . .
O11 O 0.86252(19) 0.87533(13) 0.75645(9) 0.0327(3) Uani 1 1 d . . . . .
O22 O 0.21044(18) 0.57428(15) 0.66764(9) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.71959(17) 0.79067(13) 0.58041(9) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.58266(17) 0.50440(12) 0.81048(9) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.90266(19) 0.48360(14) 0.66151(10) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.990(3) 0.496(2) 0.6782(17) 0.036(6) Uiso 1 1 d . . . . .
H3B H 0.900(3) 0.499(2) 0.6043(18) 0.031(6) Uiso 1 1 d . . . . .
C10 C 0.6862(2) 0.83291(16) 0.48692(11) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.6367(2) 0.75411(18) 0.44586(12) 0.0255(3) Uani 1 1 d . . . . .
H11 H 0.636(3) 0.670(2) 0.4828(16) 0.032(6) Uiso 1 1 d . . . . .
C12 C 0.5994(2) 0.7978(2) 0.35255(12) 0.0304(4) Uani 1 1 d . . . . .
H12 H 0.562(4) 0.743(3) 0.3262(18) 0.048(7) Uiso 1 1 d . . . . .
C13 C 0.6077(3) 0.9204(2) 0.29689(12) 0.0338(4) Uani 1 1 d . . . . .
H13 H 0.578(4) 0.952(3) 0.2334(19) 0.047(7) Uiso 1 1 d . . . . .
C14 C 0.6584(2) 0.99694(18) 0.33487(12) 0.0308(4) Uani 1 1 d . . . . .
H14 H 0.666(3) 1.081(2) 0.3009(17) 0.037(6) Uiso 1 1 d . . . . .
C15 C 0.7000(2) 0.95513(16) 0.43075(12) 0.0238(3) Uani 1 1 d . . . . .
C16 C 0.7552(2) 1.02989(16) 0.47321(13) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.764(3) 1.112(2) 0.4368(16) 0.034(6) Uiso 1 1 d . . . . .
C17 C 0.7934(2) 0.98333(16) 0.56560(13) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.836(3) 1.029(2) 0.5948(16) 0.033(6) Uiso 1 1 d . . . . .
C18 C 0.7718(2) 0.86367(15) 0.61689(11) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.8021(2) 0.81384(16) 0.72115(12) 0.0244(3) Uani 1 1 d . . . . .
C20 C 0.6523(2) 0.43740(15) 0.89861(11) 0.0197(3) Uani 1 1 d . . . . .
C21 C 0.8184(2) 0.44124(16) 0.92357(12) 0.0235(3) Uani 1 1 d . . . . .
H21 H 0.878(3) 0.488(2) 0.8806(14) 0.021(5) Uiso 1 1 d . . . . .
C22 C 0.8892(2) 0.37352(17) 1.01141(12) 0.0275(4) Uani 1 1 d . . . . .
H22 H 0.997(3) 0.377(2) 1.0282(16) 0.029(5) Uiso 1 1 d . . . . .
C23 C 0.7975(3) 0.30066(17) 1.07792(12) 0.0294(4) Uani 1 1 d . . . . .
H23 H 0.851(3) 0.255(2) 1.1376(18) 0.041(6) Uiso 1 1 d . . . . .
C24 C 0.6372(3) 0.29601(16) 1.05572(12) 0.0272(4) Uani 1 1 d . . . . .
H24 H 0.571(3) 0.250(2) 1.1000(16) 0.032(6) Uiso 1 1 d . . . . .
C25 C 0.5601(2) 0.36372(15) 0.96501(11) 0.0223(3) Uani 1 1 d . . . . .
C26 C 0.3971(2) 0.35901(16) 0.93810(12) 0.0259(3) Uani 1 1 d . . . . .
H26 H 0.340(3) 0.309(2) 0.9814(16) 0.030(5) Uiso 1 1 d . . . . .
C27 C 0.3301(2) 0.42669(17) 0.85017(12) 0.0251(3) Uani 1 1 d . . . . .
H27 H 0.221(3) 0.429(2) 0.8289(17) 0.038(6) Uiso 1 1 d . . . . .
C28 C 0.4263(2) 0.49948(15) 0.78858(11) 0.0202(3) Uani 1 1 d . . . . .
C29 C 0.3548(2) 0.57868(17) 0.69100(11) 0.0234(3) Uani 1 1 d . . . . .
C31 C 0.9181(2) 0.34380(17) 0.70387(12) 0.0268(3) Uani 1 1 d . . . . .
H31A H 0.902(3) 0.327(2) 0.7691(16) 0.029(5) Uiso 1 1 d . . . . .
H31B H 1.039(3) 0.287(2) 0.6978(16) 0.035(6) Uiso 1 1 d . . . . .
C32 C 0.7811(3) 0.31020(17) 0.66094(12) 0.0279(4) Uani 1 1 d . . . . .
H32A H 0.663(3) 0.375(2) 0.6590(14) 0.021(5) Uiso 1 1 d . . . . .
H32B H 0.777(3) 0.221(2) 0.7010(17) 0.042(6) Uiso 1 1 d . . . . .
C33 C 0.8255(3) 0.29980(18) 0.56560(13) 0.0289(4) Uani 1 1 d . . . . .
H33A H 0.940(3) 0.231(2) 0.5685(16) 0.035(6) Uiso 1 1 d . . . . .
H33B H 0.731(3) 0.276(2) 0.5450(17) 0.038(6) Uiso 1 1 d . . . . .
O4 O 0.7292(2) 0.87256(13) 0.92948(10) 0.0353(3) Uani 1 1 d . . . . .
H4 H 0.766(4) 0.866(3) 0.878(2) 0.047(7) Uiso 1 1 d . . . . .
C41 C 0.7501(3) 0.9411(2) 1.05747(14) 0.0410(5) Uani 1 1 d . . . . .
H41A H 0.622669 0.981155 1.055148 0.061 Uiso 1 1 calc GR . . . .
H41B H 0.806452 0.987546 1.081315 0.061 Uiso 1 1 calc GR . . . .
H41C H 0.781032 0.852363 1.096947 0.061 Uiso 1 1 calc GR . . . .
C42 C 0.8131(3) 0.94471(17) 0.96159(13) 0.0301(4) Uani 1 1 d . . . . .
H42 H 0.942828 0.901963 0.965011 0.036 Uiso 1 1 calc R . . . .
C43 C 0.7709(4) 1.0815(2) 0.89556(16) 0.0461(5) Uani 1 1 d . . . . .
H43A H 0.815844 1.078791 0.836098 0.069 Uiso 1 1 calc GR . . . .
H43B H 0.826306 1.129417 0.918439 0.069 Uiso 1 1 calc GR . . . .
H43C H 0.643754 1.123464 0.890115 0.069 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9928(12) . ?
Zn1 O2 2.0137(12) . ?
Zn1 N1 2.1921(13) . ?
Zn1 N2 2.1882(13) . ?
Zn1 N3 2.0438(14) . ?
O1 C19 1.274(2) . ?
O2 C29 1.266(2) . ?
O3 C33 1.414(2) . ?
O11 C19 1.234(2) . ?
O22 C29 1.244(2) . ?
N1 C10 1.371(2) . ?
N1 C18 1.322(2) . ?
N2 C20 1.370(2) . ?
N2 C28 1.329(2) . ?
N3 C31 1.488(2) . ?
C10 C11 1.415(2) . ?
C10 C15 1.422(2) . ?
C11 C12 1.372(2) . ?
C12 C13 1.409(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.417(2) . ?
C15 C16 1.414(3) . ?
C16 C17 1.359(3) . ?
C17 C18 1.402(2) . ?
C18 C19 1.520(2) . ?
C20 C21 1.414(2) . ?
C20 C25 1.421(2) . ?
C21 C22 1.370(2) . ?
C22 C23 1.414(3) . ?
C23 C24 1.360(3) . ?
C24 C25 1.422(2) . ?
C25 C26 1.406(3) . ?
C26 C27 1.363(3) . ?
C27 C28 1.402(2) . ?
C28 C29 1.513(2) . ?
C31 C32 1.517(3) . ?
C32 C33 1.511(2) . ?
O4 C42 1.428(2) . ?
C41 C42 1.509(3) . ?
C42 C43 1.508(3) . ?

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 O2 131.42(5) . . ?
O1 Zn1 N1 79.30(5) . . ?
O1 Zn1 N2 92.32(5) . . ?
O1 Zn1 N3 111.66(6) . . ?
O2 Zn1 N1 93.60(5) . . ?
O2 Zn1 N2 78.87(5) . . ?
O2 Zn1 N3 116.91(5) . . ?
N2 Zn1 N1 160.72(5) . . ?
N3 Zn1 N1 97.40(5) . . ?
N3 Zn1 N2 101.83(5) . . ?
C19 O1 Zn1 117.94(11) . . ?
C29 O2 Zn1 117.44(11) . . ?
C10 N1 Zn1 131.61(11) . . ?
C18 N1 Zn1 109.71(10) . . ?
C18 N1 C10 118.57(14) . . ?
C20 N2 Zn1 131.23(11) . . ?
C28 N2 Zn1 110.26(10) . . ?
C28 N2 C20 118.49(13) . . ?
C31 N3 Zn1 118.99(10) . . ?
N1 C10 C11 119.57(15) . . ?
N1 C10 C15 120.83(15) . . ?
C11 C10 C15 119.60(15) . . ?
C12 C11 C10 119.54(17) . . ?
C11 C12 C13 121.16(17) . . ?
C14 C13 C12 120.22(17) . . ?
C13 C14 C15 120.51(17) . . ?
C14 C15 C10 118.93(16) . . ?
C16 C15 C10 118.35(15) . . ?
C16 C15 C14 122.71(16) . . ?
C17 C16 C15 119.44(16) . . ?
C16 C17 C18 118.94(16) . . ?
N1 C18 C17 123.80(15) . . ?
N1 C18 C19 116.29(14) . . ?
C17 C18 C19 119.86(15) . . ?
O1 C19 C18 116.36(14) . . ?
O11 C19 O1 125.93(16) . . ?
O11 C19 C18 117.69(15) . . ?
N2 C20 C21 119.54(14) . . ?
N2 C20 C25 120.81(15) . . ?
C21 C20 C25 119.65(15) . . ?
C22 C21 C20 119.72(16) . . ?
C21 C22 C23 120.85(17) . . ?
C24 C23 C22 120.53(16) . . ?
C23 C24 C25 120.33(16) . . ?
C20 C25 C24 118.91(16) . . ?
C26 C25 C20 118.67(15) . . ?
C26 C25 C24 122.41(16) . . ?
C27 C26 C25 119.48(15) . . ?
C26 C27 C28 118.93(16) . . ?
N2 C28 C27 123.59(15) . . ?
N2 C28 C29 115.69(14) . . ?
C27 C28 C29 120.73(15) . . ?
O2 C29 C28 117.39(14) . . ?
O22 C29 O2 125.24(16) . . ?
O22 C29 C28 117.37(15) . . ?
N3 C31 C32 111.14(14) . . ?
C33 C32 C31 113.94(15) . . ?
O3 C33 C32 108.96(14) . . ?
O4 C42 C41 107.68(15) . . ?
O4 C42 C43 110.28(17) . . ?
C43 C42 C41 112.60(17) . . ?

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
_geom_hbond_publ_flag
O3 H3 O22 0.79(3) 1.90(3) 2.6930(19) 175(3) 2_666 yes
N3 H3A O22 0.83(3) 2.18(3) 2.9634(19) 158(2) 1_655 yes
N3 H3B O3 0.84(3) 2.15(2) 2.833(2) 138(2) . yes
O4 H4 O11 0.84(3) 1.95(3) 2.776(2) 171(3) . yes

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1946664'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;Department of Chemistry and Chemical Technology, University of Ljubljana
Slovenia
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N3 O5 Zn, C2 H6 O'
_chemical_formula_sum            'C25 H27 N3 O6 Zn'
_chemical_formula_weight         530.86
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8788(5)
_cell_length_b                   11.2689(6)
_cell_length_c                   15.3272(10)
_cell_angle_alpha                105.313(5)
_cell_angle_beta                 98.626(5)
_cell_angle_gamma                110.008(5)
_cell_volume                     1189.14(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5280
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8740
_cell_measurement_theta_min      3.0540
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.528
_exptl_absorpt_coefficient_mu    1.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8209
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.955
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.76  37.00 120.00   99
  2  ω   -114.00 -18.00   1.00    1.00    --  -41.76 -37.00 -60.00   96
  3  ω    -28.00  64.00   1.00    1.00    --   41.76 -19.00 150.00   92
  4  ω     48.00  97.00   1.00    1.00    --   41.76-125.00-120.00   49
  5  ω     71.00  97.00   1.00    4.00    --  104.43-125.00-150.00   26
  6  ω     81.00 139.00   1.00    4.00    --  104.43  45.00 -90.00   58
  7  ω     33.00 120.00   1.00    4.00    --  104.43 -61.00-180.00   87
  8  ω     31.00 130.00   1.00    4.00    --  104.43 -45.00  60.00   99
  9  ω     32.00  58.00   1.00    4.00    --  104.43-125.00-150.00   26
 10  ω     77.00 127.00   1.00    4.00    --  104.43  30.00  90.00   50
 11  ω    145.00 177.00   1.00    4.00    --  104.43  30.00  90.00   32
 12  ω     41.00  66.00   1.00    4.00    --  104.43-125.00 -90.00   25
 13  ω     85.00 111.00   1.00    4.00    --  104.43-125.00 -90.00   26
 14  ω     48.00 117.00   1.00    4.00    --  104.43-125.00   0.00   69
 15  ω    112.00 138.00   1.00    4.00    --  104.43 125.00 -30.00   26
 16  ω     23.00 136.00   1.00    4.00    --  104.43 -15.00 -90.00  113
 17  ω     85.00 110.00   1.00    4.00    --  104.43-103.00 104.00   25
 18  ω     29.00 119.00   1.00    4.00    --  104.43 -77.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0468228000
_diffrn_orient_matrix_UB_12      -0.0386177000
_diffrn_orient_matrix_UB_13      -0.0947985000
_diffrn_orient_matrix_UB_21      0.1364968000
_diffrn_orient_matrix_UB_22      -0.0533795000
_diffrn_orient_matrix_UB_23      0.0420522000
_diffrn_orient_matrix_UB_31      -0.1604827000
_diffrn_orient_matrix_UB_32      -0.1399446000
_diffrn_orient_matrix_UB_33      -0.0304380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4397
_reflns_number_total             4586
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.6823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0836
_refine_special_details          ?
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.50685(3) 0.70139(2) 0.30964(2) 0.01686(9) Uani 1 1 d . . . . .
O2 O 0.77348(16) 0.72801(12) 0.36011(8) 0.0207(2) Uani 1 1 d . . . . .
O1 O 0.27058(17) 0.53894(13) 0.23841(9) 0.0259(3) Uani 1 1 d . . . . .
O3 O 0.7417(2) 1.07592(14) 0.48890(10) 0.0327(3) Uani 1 1 d . . . . .
H3 H 0.805(4) 1.120(3) 0.542(2) 0.038(7) Uiso 1 1 d . . . . .
O22 O 1.05299(17) 0.77635(14) 0.33065(9) 0.0289(3) Uani 1 1 d . . . . .
O11 O 0.01255(18) 0.39176(14) 0.25419(10) 0.0315(3) Uani 1 1 d . . . . .
N2 N 0.61124(19) 0.69577(13) 0.18509(10) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.41634(18) 0.64149(14) 0.42478(10) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.4572(2) 0.87215(14) 0.33377(10) 0.0185(3) Uani 1 1 d . . . . .
H3A H 0.337(3) 0.844(2) 0.3171(15) 0.020(5) Uiso 1 1 d . . . . .
H3B H 0.492(3) 0.912(2) 0.3903(18) 0.022(5) Uiso 1 1 d . . . . .
C20 C 0.5212(2) 0.67275(16) 0.09434(11) 0.0183(3) Uani 1 1 d . . . . .
C21 C 0.3270(2) 0.64206(18) 0.06993(13) 0.0241(4) Uani 1 1 d . . . . .
H21 H 0.260(3) 0.637(2) 0.1165(17) 0.030(6) Uiso 1 1 d . . . . .
C22 C 0.2369(3) 0.61846(19) -0.02056(14) 0.0273(4) Uani 1 1 d . . . . .
H22 H 0.110(4) 0.596(2) -0.0369(18) 0.033(6) Uiso 1 1 d . . . . .
C23 C 0.3348(3) 0.62327(19) -0.09054(13) 0.0287(4) Uani 1 1 d . . . . .
H23 H 0.273(3) 0.606(2) -0.1514(19) 0.033(6) Uiso 1 1 d . . . . .
C24 C 0.5224(3) 0.65289(19) -0.06847(13) 0.0274(4) Uani 1 1 d . . . . .
H24 H 0.590(3) 0.656(2) -0.1128(18) 0.031(6) Uiso 1 1 d . . . . .
C25 C 0.6206(2) 0.67959(17) 0.02481(12) 0.0218(3) Uani 1 1 d . . . . .
C26 C 0.8150(3) 0.71356(19) 0.05118(13) 0.0270(4) Uani 1 1 d . . . . .
H26 H 0.880(3) 0.719(2) 0.0050(17) 0.031(6) Uiso 1 1 d . . . . .
C27 C 0.9008(2) 0.73585(19) 0.14152(13) 0.0248(4) Uani 1 1 d . . . . .
H27 H 1.031(3) 0.757(2) 0.1614(17) 0.029(6) Uiso 1 1 d . . . . .
C28 C 0.7932(2) 0.72424(16) 0.20629(11) 0.0180(3) Uani 1 1 d . . . . .
C29 C 0.8817(2) 0.74450(16) 0.30720(12) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.5017(2) 0.68823(16) 0.51914(12) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.6681(2) 0.80627(18) 0.55768(12) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.716(3) 0.852(2) 0.5194(17) 0.027(5) Uiso 1 1 d . . . . .
C12 C 0.7546(3) 0.8519(2) 0.65165(13) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.863(4) 0.932(3) 0.6768(17) 0.033(6) Uiso 1 1 d . . . . .
C13 C 0.6820(3) 0.7822(2) 0.71115(13) 0.0298(4) Uani 1 1 d . . . . .
H13 H 0.752(4) 0.816(3) 0.776(2) 0.043(7) Uiso 1 1 d . . . . .
C14 C 0.5199(3) 0.6690(2) 0.67547(13) 0.0279(4) Uani 1 1 d . . . . .
H14 H 0.469(3) 0.621(3) 0.7127(18) 0.035(6) Uiso 1 1 d . . . . .
C15 C 0.4238(2) 0.62009(18) 0.57897(13) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.2531(3) 0.50536(19) 0.53941(14) 0.0262(4) Uani 1 1 d . . . . .
H16 H 0.195(4) 0.457(3) 0.5777(19) 0.039(7) Uiso 1 1 d . . . . .
C17 C 0.1683(2) 0.46447(18) 0.44652(14) 0.0246(4) Uani 1 1 d . . . . .
H17 H 0.054(3) 0.390(2) 0.4157(17) 0.032(6) Uiso 1 1 d . . . . .
C18 C 0.2558(2) 0.53411(16) 0.39120(12) 0.0189(3) Uani 1 1 d . . . . .
C19 C 0.1699(2) 0.48377(17) 0.28599(13) 0.0222(3) Uani 1 1 d . . . . .
C31 C 0.5431(2) 0.97009(18) 0.28764(12) 0.0221(3) Uani 1 1 d . . . . .
H31A H 0.490(3) 1.032(2) 0.2944(15) 0.019(5) Uiso 1 1 d . . . . .
H31B H 0.513(3) 0.920(2) 0.2205(16) 0.022(5) Uiso 1 1 d . . . . .
C32 C 0.7537(2) 1.04121(17) 0.32863(13) 0.0231(4) Uani 1 1 d . . . . .
H32A H 0.811(3) 0.974(2) 0.3298(16) 0.026(5) Uiso 1 1 d . . . . .
H32B H 0.809(3) 1.089(2) 0.2889(16) 0.024(5) Uiso 1 1 d . . . . .
C33 C 0.8147(2) 1.14162(17) 0.42702(13) 0.0230(3) Uani 1 1 d . . . . .
H33A H 0.765(3) 1.212(2) 0.4254(16) 0.025(5) Uiso 1 1 d . . . . .
H33B H 0.950(4) 1.186(2) 0.4477(17) 0.032(6) Uiso 1 1 d . . . . .
O4 O -0.0152(2) 0.18804(17) 0.10144(11) 0.0397(4) Uani 1 1 d . . . . .
H4 H -0.012(4) 0.251(3) 0.147(2) 0.052(8) Uiso 1 1 d . . . . .
C41 C -0.1929(4) 0.0809(2) 0.07611(18) 0.0419(5) Uani 1 1 d . . . . .
H41A H -0.173(4) 0.015(3) 0.104(2) 0.058(9) Uiso 1 1 d . . . . .
H41B H -0.284(4) 0.110(3) 0.102(2) 0.049(8) Uiso 1 1 d . . . . .
C42 C -0.2579(4) 0.0174(3) -0.0286(2) 0.0497(6) Uani 1 1 d . . . . .
H42A H -0.378(5) -0.056(4) -0.045(2) 0.064(9) Uiso 1 1 d . . . . .
H42B H -0.166(5) -0.016(3) -0.052(2) 0.068(10) Uiso 1 1 d . . . . .
H42C H -0.278(5) 0.085(4) -0.059(3) 0.083(12) Uiso 1 1 d . . . . .


_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 O2 2.0150(12) . ?
Zn1 O1 2.0028(12) . ?
Zn1 N2 2.1834(14) . ?
Zn1 N1 2.1808(14) . ?
Zn1 N3 2.0433(14) . ?
O2 C29 1.264(2) . ?
O1 C19 1.274(2) . ?
O3 C33 1.422(2) . ?
O22 C29 1.239(2) . ?
O11 C19 1.234(2) . ?
N2 C20 1.376(2) . ?
N2 C28 1.324(2) . ?
N1 C10 1.373(2) . ?
N1 C18 1.326(2) . ?
N3 C31 1.490(2) . ?
C20 C21 1.414(2) . ?
C20 C25 1.416(2) . ?
C21 C22 1.371(3) . ?
C22 C23 1.414(3) . ?
C23 C24 1.365(3) . ?
C24 C25 1.419(3) . ?
C25 C26 1.410(3) . ?
C26 C27 1.363(3) . ?
C27 C28 1.402(2) . ?
C28 C29 1.520(2) . ?
C10 C11 1.413(2) . ?
C10 C15 1.423(2) . ?
C11 C12 1.370(3) . ?
C12 C13 1.415(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.419(3) . ?
C15 C16 1.414(3) . ?
C16 C17 1.358(3) . ?
C17 C18 1.402(2) . ?
C18 C19 1.519(2) . ?
C31 C32 1.517(2) . ?
C32 C33 1.515(3) . ?
O4 C41 1.415(3) . ?
C41 C42 1.499(4) . ?

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
O2 Zn1 N2 78.68(5) . . ?
O2 Zn1 N1 93.29(5) . . ?
O2 Zn1 N3 115.85(5) . . ?
O1 Zn1 O2 133.48(5) . . ?
O1 Zn1 N2 92.56(5) . . ?
O1 Zn1 N1 79.52(5) . . ?
O1 Zn1 N3 110.67(6) . . ?
N1 Zn1 N2 159.87(5) . . ?
N3 Zn1 N2 101.39(5) . . ?
N3 Zn1 N1 98.73(5) . . ?
C29 O2 Zn1 117.63(11) . . ?
C19 O1 Zn1 117.36(11) . . ?
C20 N2 Zn1 130.75(11) . . ?
C28 N2 Zn1 110.59(11) . . ?
C28 N2 C20 118.62(14) . . ?
C10 N1 Zn1 131.66(11) . . ?
C18 N1 Zn1 109.71(11) . . ?
C18 N1 C10 118.41(14) . . ?
C31 N3 Zn1 118.91(11) . . ?
N2 C20 C21 119.70(15) . . ?
N2 C20 C25 120.90(15) . . ?
C21 C20 C25 119.40(16) . . ?
C22 C21 C20 119.79(17) . . ?
C21 C22 C23 121.05(17) . . ?
C24 C23 C22 120.12(17) . . ?
C23 C24 C25 120.29(17) . . ?
C20 C25 C24 119.34(16) . . ?
C26 C25 C20 118.45(16) . . ?
C26 C25 C24 122.20(17) . . ?
C27 C26 C25 119.48(16) . . ?
C26 C27 C28 119.09(16) . . ?
N2 C28 C27 123.41(16) . . ?
N2 C28 C29 115.58(14) . . ?
C27 C28 C29 121.01(15) . . ?
O2 C29 C28 116.88(14) . . ?
O22 C29 O2 125.66(16) . . ?
O22 C29 C28 117.47(15) . . ?
N1 C10 C11 119.66(15) . . ?
N1 C10 C15 120.88(15) . . ?
C11 C10 C15 119.46(16) . . ?
C12 C11 C10 119.64(17) . . ?
C11 C12 C13 121.35(18) . . ?
C14 C13 C12 119.87(17) . . ?
C13 C14 C15 120.53(17) . . ?
C14 C15 C10 119.09(17) . . ?
C16 C15 C10 118.39(16) . . ?
C16 C15 C14 122.52(17) . . ?
C17 C16 C15 119.38(16) . . ?
C16 C17 C18 119.15(16) . . ?
N1 C18 C17 123.72(16) . . ?
N1 C18 C19 116.43(15) . . ?
C17 C18 C19 119.81(15) . . ?
O1 C19 C18 116.31(14) . . ?
O11 C19 O1 126.05(17) . . ?
O11 C19 C18 117.61(16) . . ?
N3 C31 C32 111.54(14) . . ?
C33 C32 C31 114.43(15) . . ?
O3 C33 C32 109.91(14) . . ?
O4 C41 C42 109.2(2) . . ?

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
_geom_hbond_publ_flag
O3 H3 O22 0.80(3) 1.92(3) 2.7241(19) 178(3) 2_776 yes
N3 H3A O22 0.86(2) 2.17(2) 2.9807(19) 158(2) 1_455 yes
N3 H3B O3 0.82(2) 2.17(2) 2.819(2) 136(2) . yes
O4 H4 O11 0.84(3) 1.89(3) 2.732(2) 175(3) . yes

