# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_cd212
_database_code_depnum_ccdc_archive 'CCDC 1967442'
loop_
_audit_author_name
_audit_author_address
'Hakan Erer'
;Eskisehir Osmangazi University
Turkey
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Co N4 O5, H2 O'
_chemical_formula_sum            'C24 H22 Co N4 O6'
_chemical_formula_weight         521.38
_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'
Co Co 0.3494 0.9721 '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'

_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                   8.1544(2)
_cell_length_b                   16.2063(3)
_cell_length_c                   17.1591(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.034(2)
_cell_angle_gamma                90
_cell_volume                     2245.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0180
_cell_measurement_theta_min      3.4610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90676
_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    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31732
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.744
_diffrn_reflns_theta_min         3.465
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0454
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4289
_reflns_number_total             5400
_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         1.034
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.036
_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)+(0.0464P)²+2.3305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C9(H9A,H9B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C5(H5), C11(H11), C20(H20), C24(H24), C13(H13), C23(H23),
 C10(H10), C16(H16), C12(H12), C18(H18), C17(H17), C22(H22)
;
_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
Co1 Co 0.38713(4) 0.30762(2) 0.28131(2) 0.02463(11) Uani 1 1 d . . . . .
O1 O 0.5572(2) 0.31312(11) 0.37373(10) 0.0340(4) Uani 1 1 d . . . . .
O4 O 0.9850(2) 0.26149(12) 0.70447(11) 0.0379(4) Uani 1 1 d . . . . .
O5 O 1.2357(2) 0.42988(13) 0.51443(11) 0.0387(5) Uani 1 1 d . . . . .
O3 O 0.7274(2) 0.23914(13) 0.65371(11) 0.0407(5) Uani 1 1 d . . . . .
O2 O 0.7115(2) 0.39602(14) 0.31076(11) 0.0459(5) Uani 1 1 d . . . . .
N1 N 0.2789(3) 0.41782(13) 0.25365(12) 0.0314(5) Uani 1 1 d . . . . .
N4 N -0.2823(2) 0.25408(12) -0.16223(13) 0.0284(4) Uani 1 1 d . . . . .
N2 N 0.0763(3) 0.50802(13) 0.23354(13) 0.0319(5) Uani 1 1 d . . . . .
N3 N -0.3810(3) 0.31796(14) -0.06568(14) 0.0369(5) Uani 1 1 d . . . . .
C4 C 0.8977(3) 0.31427(14) 0.57637(14) 0.0251(5) Uani 1 1 d . . . . .
C7 C 0.9654(3) 0.39494(15) 0.44137(14) 0.0266(5) Uani 1 1 d . . . . .
H7 H 0.9881 0.4221 0.3964 0.032 Uiso 1 1 calc R . . . .
C2 C 0.8138(3) 0.35477(14) 0.44181(13) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.7811(3) 0.31420(14) 0.50903(14) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.6809 0.2869 0.5091 0.030 Uiso 1 1 calc R . . . .
C8 C 0.8655(3) 0.26899(15) 0.64865(14) 0.0285(5) Uani 1 1 d . . . . .
C6 C 1.0822(3) 0.39390(15) 0.50889(14) 0.0262(5) Uani 1 1 d . . . . .
C5 C 1.0479(3) 0.35418(15) 0.57621(14) 0.0279(5) Uani 1 1 d . . . . .
H5 H 1.1258 0.3543 0.6213 0.034 Uiso 1 1 calc R . . . .
C1 C 0.6870(3) 0.35591(16) 0.36885(14) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.3445(3) 0.49583(16) 0.25451(16) 0.0361(6) Uani 1 1 d . . . . .
H11 H 0.4569 0.5083 0.2624 0.043 Uiso 1 1 calc R . . . .
C20 C -0.2432(3) 0.45156(16) 0.10782(16) 0.0333(6) Uani 1 1 d . . . . .
H20 H -0.2633 0.4148 0.1470 0.040 Uiso 1 1 calc R . . . .
C19 C -0.2979(3) 0.43234(16) 0.02967(16) 0.0335(6) Uani 1 1 d . . . . .
C15 C -0.1590(3) 0.52450(15) 0.12866(16) 0.0305(5) Uani 1 1 d . . . . .
C24 C -0.2527(3) 0.27680(16) -0.08785(16) 0.0319(6) Uani 1 1 d . . . . .
H24 H -0.1548 0.2656 -0.0548 0.038 Uiso 1 1 calc R . . . .
C13 C 0.1167(3) 0.42797(16) 0.24048(16) 0.0358(6) Uani 1 1 d . . . . .
H13 H 0.0403 0.3850 0.2365 0.043 Uiso 1 1 calc R . . . .
C23 C -0.4398(3) 0.28179(17) -0.18924(17) 0.0358(6) Uani 1 1 d . . . . .
H23 H -0.4951 0.2744 -0.2399 0.043 Uiso 1 1 calc R . . . .
C10 C 1.4573(3) 0.50104(18) 0.46594(16) 0.0376(6) Uani 1 1 d . . . . .
H10 H 1.5044 0.5248 0.4250 0.045 Uiso 1 1 calc R . . . .
C14 C -0.0931(3) 0.54097(17) 0.21408(16) 0.0361(6) Uani 1 1 d . . . . .
H14A H -0.0924 0.5999 0.2239 0.043 Uiso 1 1 calc R . . . .
H14B H -0.1650 0.5152 0.2475 0.043 Uiso 1 1 calc R . . . .
C16 C -0.1312(3) 0.57977(17) 0.06989(17) 0.0373(6) Uani 1 1 d . . . . .
H16 H -0.0756 0.6290 0.0830 0.045 Uiso 1 1 calc R . . . .
C12 C 0.2215(3) 0.55146(17) 0.24220(17) 0.0378(6) Uani 1 1 d . . . . .
H12 H 0.2329 0.6085 0.2400 0.045 Uiso 1 1 calc R . . . .
C18 C -0.2696(3) 0.48806(18) -0.02829(17) 0.0397(6) Uani 1 1 d . . . . .
H18 H -0.3064 0.4763 -0.0809 0.048 Uiso 1 1 calc R . . . .
C17 C -0.1864(4) 0.56141(18) -0.00805(18) 0.0415(7) Uani 1 1 d . . . . .
H17 H -0.1677 0.5985 -0.0472 0.050 Uiso 1 1 calc R . . . .
C22 C -0.5010(3) 0.32150(18) -0.13019(19) 0.0419(7) Uani 1 1 d . . . . .
H22 H -0.6044 0.3464 -0.1328 0.050 Uiso 1 1 calc R . . . .
C9 C 1.2825(3) 0.46675(19) 0.44803(16) 0.0385(6) Uani 1 1 d . . . . .
H9A H 1.2062 0.5111 0.4305 0.046 Uiso 1 1 calc R . . . .
H9B H 1.2778 0.4265 0.4060 0.046 Uiso 1 1 calc R . . . .
C21 C -0.3908(4) 0.35165(19) 0.01297(19) 0.0443(7) Uani 1 1 d . . . . .
H21A H -0.3465 0.3113 0.0521 0.053 Uiso 1 1 calc R . . . .
H21B H -0.5063 0.3603 0.0185 0.053 Uiso 1 1 calc R . . . .
O6 O 0.4112(4) 0.2759(3) 0.5932(3) 0.1187(14) Uani 1 1 d . . . . .
H6A H 0.5130 0.2732 0.6123 0.178 Uiso 1 1 d G . . . .
H6B H 0.3888 0.3244 0.5761 0.178 Uiso 1 1 d G . . . .


_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
Co1 O1 1.9572(17) . ?
Co1 O4 1.9810(19) 4_565 ?
Co1 N1 2.019(2) . ?
Co1 N4 2.055(2) 4_666 ?
O1 C1 1.278(3) . ?
O4 Co1 1.9809(19) 4_666 ?
O4 C8 1.273(3) . ?
O5 C6 1.372(3) . ?
O5 C9 1.387(3) . ?
O3 C8 1.240(3) . ?
O2 C1 1.229(3) . ?
N1 C11 1.372(3) . ?
N1 C13 1.320(3) . ?
N4 Co1 2.055(2) 4_565 ?
N4 C24 1.318(3) . ?
N4 C23 1.378(3) . ?
N2 C13 1.340(3) . ?
N2 C14 1.475(3) . ?
N2 C12 1.368(3) . ?
N3 C24 1.340(3) . ?
N3 C22 1.373(4) . ?
N3 C21 1.468(4) . ?
C4 C3 1.390(3) . ?
C4 C8 1.496(3) . ?
C4 C5 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.398(3) . ?
C7 C6 1.393(3) . ?
C2 C3 1.385(3) . ?
C2 C1 1.508(3) . ?
C3 H3 0.9300 . ?
C6 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.343(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.388(4) . ?
C20 C15 1.388(4) . ?
C19 C18 1.386(4) . ?
C19 C21 1.518(4) . ?
C15 C14 1.513(4) . ?
C15 C16 1.391(4) . ?
C24 H24 0.9300 . ?
C13 H13 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.353(4) . ?
C10 C10 1.275(5) 3_866 ?
C10 H10 0.9300 . ?
C10 C9 1.521(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.388(4) . ?
C17 H17 0.9300 . ?
C22 H22 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O4 105.03(8) . 4_565 ?
O1 Co1 N1 112.77(8) . . ?
O1 Co1 N4 95.00(8) . 4_666 ?
O4 Co1 N1 123.18(9) 4_565 . ?
O4 Co1 N4 113.50(9) 4_565 4_666 ?
N1 Co1 N4 103.92(9) . 4_666 ?
C1 O1 Co1 118.11(16) . . ?
C8 O4 Co1 102.57(16) . 4_666 ?
C6 O5 C9 118.7(2) . . ?
C11 N1 Co1 130.96(18) . . ?
C13 N1 Co1 123.02(18) . . ?
C13 N1 C11 105.5(2) . . ?
C24 N4 Co1 123.25(17) . 4_565 ?
C24 N4 C23 105.7(2) . . ?
C23 N4 Co1 131.03(18) . 4_565 ?
C13 N2 C14 125.6(2) . . ?
C13 N2 C12 106.9(2) . . ?
C12 N2 C14 127.4(2) . . ?
C24 N3 C22 106.8(2) . . ?
C24 N3 C21 126.2(2) . . ?
C22 N3 C21 127.0(2) . . ?
C3 C4 C8 120.7(2) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 C8 119.2(2) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C2 119.5(2) . . ?
C7 C2 C1 119.6(2) . . ?
C3 C2 C7 119.9(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
O4 C8 C4 117.8(2) . . ?
O3 C8 O4 121.1(2) . . ?
O3 C8 C4 121.1(2) . . ?
O5 C6 C7 124.3(2) . . ?
O5 C6 C5 115.4(2) . . ?
C5 C6 C7 120.4(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
O1 C1 C2 114.6(2) . . ?
O2 C1 O1 124.7(2) . . ?
O2 C1 C2 120.6(2) . . ?
N1 C11 H11 125.2 . . ?
C12 C11 N1 109.6(2) . . ?
C12 C11 H11 125.2 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C15 121.4(3) . . ?
C15 C20 H20 119.3 . . ?
C20 C19 C21 117.4(3) . . ?
C18 C19 C20 118.9(2) . . ?
C18 C19 C21 123.7(3) . . ?
C20 C15 C14 119.7(2) . . ?
C20 C15 C16 119.1(2) . . ?
C16 C15 C14 121.1(2) . . ?
N4 C24 N3 111.7(2) . . ?
N4 C24 H24 124.2 . . ?
N3 C24 H24 124.2 . . ?
N1 C13 N2 111.3(2) . . ?
N1 C13 H13 124.3 . . ?
N2 C13 H13 124.3 . . ?
N4 C23 H23 125.5 . . ?
C22 C23 N4 109.1(2) . . ?
C22 C23 H23 125.5 . . ?
C10 C10 H10 118.2 3_866 . ?
C10 C10 C9 123.5(4) 3_866 . ?
C9 C10 H10 118.2 . . ?
N2 C14 C15 110.5(2) . . ?
N2 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
N2 C12 H12 126.6 . . ?
C11 C12 N2 106.7(2) . . ?
C11 C12 H12 126.6 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
N3 C22 H22 126.6 . . ?
C23 C22 N3 106.7(2) . . ?
C23 C22 H22 126.6 . . ?
O5 C9 C10 110.5(2) . . ?
O5 C9 H9A 109.6 . . ?
O5 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N3 C21 C19 113.8(2) . . ?
N3 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
C19 C21 H21A 108.8 . . ?
C19 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
H6A O6 H6B 109.5 . . ?

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
O6 H6A O3 0.85 1.88 2.708(4) 165.9 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd026
_database_code_depnum_ccdc_archive 'CCDC 1967445'
loop_
_audit_author_name
_audit_author_address
'Hakan Erer'
;Eskisehir Osmangazi University
Turkey
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N4 O5 Zn, 2(H2 O)'
_chemical_formula_sum            'C24 H24 N4 O7 Zn'
_chemical_formula_weight         545.84
_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                   8.2964(5)
_cell_length_b                   17.7264(11)
_cell_length_c                   16.8112(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.546(2)
_cell_angle_gamma                90
_cell_volume                     2444.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            119060
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5271
_reflns_number_total             6090
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         0.756
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6090
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.1147
_refine_ls_restrained_S_all      1.393
_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)+15.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2009
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H6A
 2 with sigma of 0.02
 O4-H7AB
 2 with sigma of 0.02
 O4-H7B
 2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O7) = Uanis(O7A)
4. Others
 Sof(O7A)=Sof(H7AA)=Sof(H7AB)=1-FVAR(1)
 Sof(O7)=Sof(H7A)=Sof(H7B)=FVAR(1)
5.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B), O7A(H7AA,H7AB)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C10(H10), C11(H11), C13(H13), C18(H18), C20(H20),
 C12(H12), C19(H19), C17(H17), C16(H16), C23(H23), C24(H24)
;
_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 0.39365(8) 0.29383(4) 0.32167(4) 0.02760(18) Uani 1 1 d . . . . .
O5 O 1.2276(5) 0.4320(3) 0.5551(2) 0.0356(10) Uani 1 1 d . . . . .
O1 O 0.5755(5) 0.3117(3) 0.4062(3) 0.0430(12) Uani 1 1 d . . . . .
O3 O 0.9702(5) 0.2797(3) 0.7478(3) 0.0463(12) Uani 1 1 d . . . . .
O4 O 0.7115(6) 0.2711(3) 0.6961(3) 0.0519(14) Uani 1 1 d D . . . .
N3 N 0.2421(6) 0.2506(3) 0.3927(3) 0.0322(11) Uani 1 1 d . . . . .
O2 O 0.7365(6) 0.3773(3) 0.3378(3) 0.0556(14) Uani 1 1 d D . . . .
N1 N 0.3011(6) 0.3905(3) 0.2745(3) 0.0351(12) Uani 1 1 d . . . . .
N2 N 0.1221(7) 0.4728(3) 0.2183(3) 0.0427(13) Uani 1 1 d . . . . .
N4 N 0.0417(7) 0.1947(3) 0.4397(3) 0.0376(12) Uani 1 1 d . . . . .
C4 C 0.8926(6) 0.3303(3) 0.6178(3) 0.0238(11) Uani 1 1 d . . . . .
C2 C 0.8222(6) 0.3551(3) 0.4766(3) 0.0235(11) Uani 1 1 d . . . . .
C3 C 0.7837(7) 0.3239(3) 0.5471(3) 0.0260(11) Uani 1 1 d . . . . .
H3 H 0.6853 0.2988 0.5470 0.031 Uiso 1 1 calc R . . . .
C1 C 0.7039(7) 0.3480(4) 0.3995(3) 0.0331(13) Uani 1 1 d . . . . .
C7 C 0.9697(6) 0.3929(3) 0.4769(3) 0.0249(11) Uani 1 1 d . . . . .
H7 H 0.9957 0.4142 0.4299 0.030 Uiso 1 1 calc R . . . .
C6 C 1.0370(7) 0.3676(3) 0.6187(3) 0.0271(12) Uani 1 1 d . . . . .
H6 H 1.1087 0.3722 0.6665 0.033 Uiso 1 1 calc R . . . .
C10 C 1.4650(7) 0.4689(4) 0.5074(4) 0.0340(13) Uani 1 1 d . . . . .
H10 H 1.5292 0.4318 0.5354 0.041 Uiso 1 1 calc R . . . .
C8 C 1.0768(6) 0.3985(3) 0.5480(3) 0.0261(11) Uani 1 1 d . . . . .
C9 C 1.2881(7) 0.4521(3) 0.4831(4) 0.0316(13) Uani 1 1 d . . . . .
H9A H 1.2313 0.4961 0.4586 0.038 Uiso 1 1 calc R . . . .
H9B H 1.2737 0.4109 0.4448 0.038 Uiso 1 1 calc R . . . .
C5 C 0.8524(7) 0.2912(4) 0.6922(3) 0.0324(13) Uani 1 1 d . . . . .
C11 C 0.3717(9) 0.4615(4) 0.2786(4) 0.0430(16) Uani 1 1 d . . . . .
H11 H 0.4780 0.4726 0.3017 0.052 Uiso 1 1 calc R . . . .
C13 C 0.1512(8) 0.4009(4) 0.2374(4) 0.0433(16) Uani 1 1 d . . . . .
H13 H 0.0750 0.3625 0.2259 0.052 Uiso 1 1 calc R . . . .
C18 C 0.2771(8) 0.2476(3) 0.4750(4) 0.0351(14) Uani 1 1 d . . . . .
H18 H 0.3708 0.2664 0.5058 0.042 Uiso 1 1 calc R . . . .
C20 C 0.0994(8) 0.2185(4) 0.3738(4) 0.0385(15) Uani 1 1 d . . . . .
H20 H 0.0453 0.2130 0.3215 0.046 Uiso 1 1 calc R . . . .
C12 C 0.2627(9) 0.5114(4) 0.2440(4) 0.0472(17) Uani 1 1 d . . . . .
H12 H 0.2794 0.5629 0.2384 0.057 Uiso 1 1 calc R . . . .
C19 C 0.1536(9) 0.2128(4) 0.5041(4) 0.0434(16) Uani 1 1 d . . . . .
H19 H 0.1466 0.2032 0.5579 0.052 Uiso 1 1 calc R . . . .
C15 C -0.0137(8) 0.5019(4) 0.0814(4) 0.0451(17) Uani 1 1 d . . . . .
C22 C -0.0561(9) 0.0709(4) 0.4723(5) 0.053(2) Uani 1 1 d . . . . .
C17 C 0.0423(11) 0.5633(4) -0.0378(5) 0.062(2) Uani 1 1 d . . . . .
H17 H 0.0712 0.6069 -0.0631 0.074 Uiso 1 1 calc R . . . .
C16 C 0.0289(11) 0.5652(4) 0.0428(5) 0.059(2) Uani 1 1 d . . . . .
H16 H 0.0490 0.6100 0.0713 0.071 Uiso 1 1 calc R . . . .
C14 C -0.0262(10) 0.5029(5) 0.1700(5) 0.058(2) Uani 1 1 d . . . . .
H14A H -0.0438 0.5542 0.1867 0.070 Uiso 1 1 calc R . . . .
H14B H -0.1192 0.4729 0.1796 0.070 Uiso 1 1 calc R . . . .
C21 C -0.1060(10) 0.1497(5) 0.4422(6) 0.062(2) Uani 1 1 d . . . . .
H21A H -0.1691 0.1468 0.3889 0.075 Uiso 1 1 calc R . . . .
H21B H -0.1729 0.1733 0.4779 0.075 Uiso 1 1 calc R . . . .
C23 C -0.0077(11) 0.0189(5) 0.4202(6) 0.064(2) Uani 1 1 d . . . . .
H23 H -0.0125 0.0306 0.3659 0.077 Uiso 1 1 calc R . . . .
C24 C -0.0485(11) 0.0513(4) 0.5511(6) 0.065(3) Uani 1 1 d . . . . .
H24 H -0.0821 0.0859 0.5869 0.078 Uiso 1 1 calc R . . . .
O6 O 0.7891(12) 0.3122(5) 0.1938(5) 0.101(3) Uani 1 1 d . . . . .
H6A H 0.7468 0.3403 0.2260 0.152 Uiso 1 1 d DG . . . .
H6B H 0.7740 0.2676 0.2096 0.152 Uiso 1 1 d G . . . .
O7 O 0.407(9) 0.327(7) 0.675(7) 0.103(9) Uani 0.20(9) 1 d . . P A 1
H7A H 0.4082 0.3338 0.6249 0.154 Uiso 0.20(9) 1 d G . P A 1
H7B H 0.4717 0.2899 0.6869 0.154 Uiso 0.20(9) 1 d DG . P A 1
O7A O 0.432(3) 0.357(3) 0.6969(19) 0.103(9) Uani 0.80(9) 1 d . . P A 2
H7AA H 0.3869 0.3872 0.6606 0.154 Uiso 0.80(9) 1 d G . P A 2
H7AB H 0.5216 0.3416 0.6841 0.154 Uiso 0.80(9) 1 d DG . P A 2


_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 1.939(4) . ?
Zn1 O3 1.969(4) 4_565 ?
Zn1 N3 2.010(5) . ?
Zn1 N1 1.994(5) . ?
O5 C8 1.374(6) . ?
O5 C9 1.424(7) . ?
O1 C1 1.264(7) . ?
O3 Zn1 1.969(4) 4_666 ?
O3 C5 1.264(7) . ?
O4 C5 1.233(7) . ?
N3 C18 1.373(8) . ?
N3 C20 1.310(8) . ?
O2 C1 1.226(8) . ?
N1 C11 1.386(8) . ?
N1 C13 1.319(8) . ?
N2 C13 1.327(9) . ?
N2 C12 1.366(9) . ?
N2 C14 1.470(9) . ?
N4 C20 1.340(8) . ?
N4 C19 1.356(9) . ?
N4 C21 1.467(9) . ?
C4 C3 1.387(7) . ?
C4 C6 1.366(8) . ?
C4 C5 1.510(7) . ?
C2 C3 1.388(7) . ?
C2 C1 1.510(7) . ?
C2 C7 1.395(8) . ?
C7 C8 1.383(7) . ?
C6 C8 1.392(8) . ?
C10 C10 1.287(12) 3_866 ?
C10 C9 1.494(8) . ?
C11 C12 1.335(10) . ?
C18 C19 1.348(9) . ?
C15 C17 1.370(11) 3_565 ?
C15 C16 1.369(10) . ?
C15 C14 1.510(11) . ?
C22 C21 1.522(11) . ?
C22 C23 1.373(11) . ?
C22 C24 1.362(12) . ?
C17 C15 1.370(11) 3_565 ?
C17 C16 1.376(12) . ?
C23 C24 1.390(12) 3_556 ?
C24 C23 1.390(12) 3_556 ?

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 O3 106.3(2) . 4_565 ?
O1 Zn1 N3 96.5(2) . . ?
O1 Zn1 N1 111.3(2) . . ?
O3 Zn1 N3 114.2(2) 4_565 . ?
O3 Zn1 N1 117.4(2) 4_565 . ?
N1 Zn1 N3 109.0(2) . . ?
C8 O5 C9 117.8(4) . . ?
C1 O1 Zn1 126.3(4) . . ?
C5 O3 Zn1 106.6(4) . 4_666 ?
C18 N3 Zn1 123.8(4) . . ?
C20 N3 Zn1 130.1(4) . . ?
C20 N3 C18 106.0(5) . . ?
C11 N1 Zn1 128.7(4) . . ?
C13 N1 Zn1 126.1(5) . . ?
C13 N1 C11 105.0(6) . . ?
C13 N2 C12 106.8(6) . . ?
C13 N2 C14 126.1(6) . . ?
C12 N2 C14 126.7(6) . . ?
C20 N4 C19 107.4(5) . . ?
C20 N4 C21 126.7(6) . . ?
C19 N4 C21 125.6(6) . . ?
C3 C4 C5 118.4(5) . . ?
C6 C4 C3 120.5(5) . . ?
C6 C4 C5 121.0(5) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 C7 120.1(5) . . ?
C7 C2 C1 120.1(5) . . ?
C4 C3 C2 119.8(5) . . ?
O1 C1 C2 114.5(5) . . ?
O2 C1 O1 125.9(6) . . ?
O2 C1 C2 119.6(6) . . ?
C8 C7 C2 119.2(5) . . ?
C4 C6 C8 120.0(5) . . ?
C10 C10 C9 124.8(8) 3_866 . ?
O5 C8 C7 124.5(5) . . ?
O5 C8 C6 115.1(5) . . ?
C7 C8 C6 120.4(5) . . ?
O5 C9 C10 105.9(5) . . ?
O3 C5 C4 116.4(5) . . ?
O4 C5 O3 123.3(5) . . ?
O4 C5 C4 120.3(5) . . ?
C12 C11 N1 109.0(6) . . ?
N1 C13 N2 112.0(6) . . ?
C19 C18 N3 109.0(6) . . ?
N3 C20 N4 110.9(6) . . ?
C11 C12 N2 107.3(6) . . ?
C18 C19 N4 106.6(6) . . ?
C17 C15 C14 120.4(7) 3_565 . ?
C16 C15 C17 118.3(7) . 3_565 ?
C16 C15 C14 121.3(7) . . ?
C23 C22 C21 119.6(8) . . ?
C24 C22 C21 121.9(7) . . ?
C24 C22 C23 118.3(8) . . ?
C15 C17 C16 121.0(7) 3_565 . ?
C15 C16 C17 120.7(7) . . ?
N2 C14 C15 111.5(6) . . ?
N4 C21 C22 108.7(6) . . ?
C22 C23 C24 119.6(8) . 3_556 ?
C22 C24 C23 122.1(8) . 3_556 ?

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
O6 H6A O2 0.85 2.00 2.774(9) 150.4 .
O6 H6B O7 0.85 2.14 2.69(12) 122.6 4_665
O7 H7B O4 0.85 2.00 2.68(8) 136.8 .
O7A H7AB O4 0.85 2.00 2.78(2) 152.4 .

####################################################################### 
# 
# 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_cd294
_database_code_depnum_ccdc_archive 'CCDC 1967443'
loop_
_audit_author_name
_audit_author_address
'Hakan Erer'
;Eskisehir Osmangazi University
Turkey
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Co N4 O5, 2(H2 O)'
_chemical_formula_sum            'C24 H24 Co N4 O7'
_chemical_formula_weight         539.40
_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'
Co Co 0.3494 0.9721 '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'

_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                   8.3011(6)
_cell_length_b                   17.7049(14)
_cell_length_c                   16.8818(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.892(2)
_cell_angle_gamma                90
_cell_volume                     2444.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7675
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28322
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.959
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3759
_reflns_number_total             4939
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         0.539
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0938
_refine_ls_restrained_S_all      1.229
_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)+16.2885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1896
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H6A
 2 with sigma of 0.02
 O4-H7B
 2 with sigma of 0.02
 O4-H7AB
 2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O6) = Uanis(O7) = Uanis(O7A)
4. Others
 Sof(O7A)=Sof(H7AA)=Sof(H7AB)=1-FVAR(1)
 Sof(O7)=Sof(H7A)=Sof(H7B)=FVAR(1)
5.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B), O7A(H7AA,H7AB)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C6(H6), C7(H7), C18(H18), C19(H19), C13(H13), C20(H20),
 C11(H11), C24(H24), C12(H12), C23(H23), C17(H17), C16(H16)
;
_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
Co1 Co 0.60416(9) 0.29085(5) 0.67550(5) 0.0266(2) Uani 1 1 d . . . . .
O5 O -0.2338(5) 0.4319(3) 0.4422(2) 0.0378(11) Uani 1 1 d . . . . .
O1 O 0.4286(5) 0.3112(3) 0.5845(3) 0.0422(12) Uani 1 1 d . . . . .
O3 O 0.0073(5) 0.2849(3) 0.2424(2) 0.0426(11) Uani 1 1 d . . . . .
O4 O 0.2650(5) 0.2686(3) 0.2950(3) 0.0463(13) Uani 1 1 d D . . . .
N3 N 0.6946(6) 0.3905(3) 0.7229(3) 0.0341(12) Uani 1 1 d . . . . .
O2 O 0.2678(6) 0.3709(3) 0.6567(3) 0.0575(15) Uani 1 1 d D . . . .
N1 N 0.7610(6) 0.2489(3) 0.6062(3) 0.0354(12) Uani 1 1 d . . . . .
N4 N 0.8718(7) 0.4739(3) 0.7812(3) 0.0427(14) Uani 1 1 d . . . . .
N2 N 0.9625(7) 0.1950(3) 0.5600(3) 0.0371(13) Uani 1 1 d . . . . .
C3 C 0.2091(7) 0.3238(3) 0.4454(3) 0.0267(13) Uani 1 1 d . . . . .
H3 H 0.3071 0.2986 0.4447 0.032 Uiso 1 1 calc R . . . .
C2 C 0.1761(7) 0.3537(3) 0.5165(3) 0.0256(12) Uani 1 1 d . . . . .
C4 C 0.0948(7) 0.3313(3) 0.3744(3) 0.0243(12) Uani 1 1 d . . . . .
C1 C 0.2986(8) 0.3452(4) 0.5935(4) 0.0335(14) Uani 1 1 d . . . . .
C8 C -0.0832(7) 0.3984(3) 0.4480(3) 0.0258(12) Uani 1 1 d . . . . .
C5 C 0.1264(7) 0.2933(4) 0.2994(3) 0.0298(13) Uani 1 1 d . . . . .
C10 C -0.4661(7) 0.4690(4) 0.4923(4) 0.0348(14) Uani 1 1 d . . . . .
H10 H -0.5329 0.4321 0.4645 0.042 Uiso 1 1 calc R . . . .
C6 C -0.0493(7) 0.3689(3) 0.3760(3) 0.0286(13) Uani 1 1 d . . . . .
H6 H -0.1247 0.3748 0.3288 0.034 Uiso 1 1 calc R . . . .
C7 C 0.0291(7) 0.3913(3) 0.5179(3) 0.0272(13) Uani 1 1 d . . . . .
H7 H 0.0070 0.4115 0.5658 0.033 Uiso 1 1 calc R . . . .
C9 C -0.2893(7) 0.4512(4) 0.5154(4) 0.0332(14) Uani 1 1 d . . . . .
H9A H -0.2300 0.4947 0.5405 0.040 Uiso 1 1 calc R . . . .
H9B H -0.2733 0.4092 0.5528 0.040 Uiso 1 1 calc R . . . .
O6 O 0.2114(9) 0.3159(5) 0.8049(4) 0.0871(19) Uani 1 1 d . . . . .
H6A H 0.2600 0.3377 0.7708 0.131 Uiso 1 1 d DG . . . .
H6B H 0.1609 0.2793 0.7791 0.131 Uiso 1 1 d G . . . .
C18 C 0.6206(8) 0.4599(4) 0.7198(4) 0.0420(17) Uani 1 1 d . . . . .
H18 H 0.5127 0.4699 0.6968 0.050 Uiso 1 1 calc R . . . .
C19 C 0.7287(9) 0.5114(4) 0.7555(4) 0.0451(17) Uani 1 1 d . . . . .
H19 H 0.7096 0.5626 0.7615 0.054 Uiso 1 1 calc R . . . .
C13 C 0.9041(8) 0.2183(4) 0.6259(4) 0.0432(16) Uani 1 1 d . . . . .
H13 H 0.9594 0.2130 0.6784 0.052 Uiso 1 1 calc R . . . .
C20 C 0.8458(8) 0.4013(4) 0.7606(4) 0.0425(17) Uani 1 1 d . . . . .
H20 H 0.9241 0.3634 0.7715 0.051 Uiso 1 1 calc R . . . .
C11 C 0.7237(9) 0.2461(4) 0.5230(4) 0.0403(16) Uani 1 1 d . . . . .
H11 H 0.6282 0.2642 0.4919 0.048 Uiso 1 1 calc R . . . .
C22 C 1.0113(8) 0.5025(4) 0.9187(4) 0.0428(17) Uani 1 1 d . . . . .
C21 C 1.0216(9) 0.5042(5) 0.8301(5) 0.052(2) Uani 1 1 d . . . . .
H21A H 1.0380 0.5558 0.8140 0.063 Uiso 1 1 calc R . . . .
H21B H 1.1148 0.4746 0.8208 0.063 Uiso 1 1 calc R . . . .
C24 C 1.0404(10) 0.4370(4) 0.9617(5) 0.060(2) Uani 1 1 d . . . . .
H24 H 1.0681 0.3935 0.9361 0.072 Uiso 1 1 calc R . . . .
C12 C 0.8481(9) 0.2129(4) 0.4946(4) 0.0476(17) Uani 1 1 d . . . . .
H12 H 0.8547 0.2040 0.4410 0.057 Uiso 1 1 calc R . . . .
C23 C 0.9706(11) 0.5657(4) 0.9575(5) 0.061(2) Uani 1 1 d . . . . .
H23 H 0.9501 0.6108 0.9293 0.073 Uiso 1 1 calc R . . . .
C15 C 1.0590(10) 0.0715(4) 0.5286(6) 0.061(2) Uani 1 1 d . . . . .
C14 C 1.1095(10) 0.1508(5) 0.5585(6) 0.066(2) Uani 1 1 d . . . . .
H14A H 1.1743 0.1483 0.6120 0.080 Uiso 1 1 calc R . . . .
H14B H 1.1750 0.1744 0.5229 0.080 Uiso 1 1 calc R . . . .
C17 C 1.0478(12) 0.0509(5) 0.4483(6) 0.075(3) Uani 1 1 d . . . . .
H17 H 1.0798 0.0854 0.4125 0.090 Uiso 1 1 calc R . . . .
C16 C 1.0101(12) 0.0200(5) 0.5805(6) 0.075(3) Uani 1 1 d . . . . .
H16 H 1.0154 0.0321 0.6345 0.090 Uiso 1 1 calc R . . . .
O7 O 0.5572(19) 0.3532(16) 0.3024(13) 0.0871(19) Uani 0.57(4) 1 d . . P A 1
H7A H 0.5740 0.3745 0.3481 0.131 Uiso 0.57(4) 1 d G . P A 1
H7B H 0.4614 0.3346 0.2935 0.131 Uiso 0.57(4) 1 d DG . P A 1
O7A O 0.569(3) 0.326(2) 0.3261(17) 0.0871(19) Uani 0.43(4) 1 d . . P A 2
H7AA H 0.6212 0.2950 0.3599 0.131 Uiso 0.43(4) 1 d G . P A 2
H7AB H 0.4718 0.3248 0.3361 0.131 Uiso 0.43(4) 1 d DG . P A 2


_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
Co1 O1 1.960(4) . ?
Co1 O3 2.008(4) 4_666 ?
Co1 N3 2.027(5) . ?
Co1 N1 2.034(5) . ?
O5 C8 1.372(7) . ?
O5 C9 1.433(7) . ?
O1 C1 1.268(8) . ?
O3 Co1 2.008(4) 4_565 ?
O3 C5 1.264(7) . ?
O4 C5 1.244(7) . ?
N3 C18 1.371(8) . ?
N3 C20 1.321(8) . ?
O2 C1 1.227(8) . ?
N1 C13 1.296(8) . ?
N1 C11 1.386(8) . ?
N4 C19 1.365(9) . ?
N4 C20 1.340(9) . ?
N4 C21 1.471(8) . ?
N2 C13 1.352(8) . ?
N2 C12 1.364(9) . ?
N2 C14 1.452(9) . ?
C3 C2 1.381(8) . ?
C3 C4 1.401(7) . ?
C2 C1 1.514(8) . ?
C2 C7 1.393(8) . ?
C4 C5 1.497(8) . ?
C4 C6 1.373(8) . ?
C8 C6 1.396(8) . ?
C8 C7 1.378(8) . ?
C10 C10 1.281(12) 3_466 ?
C10 C9 1.486(8) . ?
C18 C19 1.346(10) . ?
C11 C12 1.345(10) . ?
C22 C21 1.513(10) . ?
C22 C24 1.368(10) . ?
C22 C23 1.367(10) . ?
C24 C23 1.384(11) 3_767 ?
C23 C24 1.384(11) 3_767 ?
C15 C14 1.526(12) . ?
C15 C17 1.390(12) . ?
C15 C16 1.374(11) . ?
C17 C16 1.401(12) 3_756 ?
C16 C17 1.401(12) 3_756 ?

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 Co1 O3 104.35(19) . 4_666 ?
O1 Co1 N3 108.9(2) . . ?
O1 Co1 N1 94.6(2) . . ?
O3 Co1 N3 121.1(2) 4_666 . ?
O3 Co1 N1 115.9(2) 4_666 . ?
N3 Co1 N1 108.3(2) . . ?
C8 O5 C9 117.7(4) . . ?
C1 O1 Co1 121.8(4) . . ?
C5 O3 Co1 99.8(4) . 4_565 ?
C18 N3 Co1 129.2(4) . . ?
C20 N3 Co1 125.0(5) . . ?
C20 N3 C18 105.7(6) . . ?
C13 N1 Co1 130.9(5) . . ?
C13 N1 C11 106.2(6) . . ?
C11 N1 Co1 122.8(4) . . ?
C19 N4 C21 127.3(6) . . ?
C20 N4 C19 106.9(6) . . ?
C20 N4 C21 125.4(6) . . ?
C13 N2 C12 107.2(5) . . ?
C13 N2 C14 126.8(7) . . ?
C12 N2 C14 125.6(6) . . ?
C2 C3 C4 120.0(5) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 C7 120.2(5) . . ?
C7 C2 C1 119.6(5) . . ?
C3 C4 C5 119.3(5) . . ?
C6 C4 C3 119.6(5) . . ?
C6 C4 C5 120.9(5) . . ?
O1 C1 C2 113.9(5) . . ?
O2 C1 O1 126.1(6) . . ?
O2 C1 C2 120.0(6) . . ?
O5 C8 C6 114.6(5) . . ?
O5 C8 C7 125.1(5) . . ?
C7 C8 C6 120.3(5) . . ?
O3 C5 C4 118.0(5) . . ?
O4 C5 O3 121.6(5) . . ?
O4 C5 C4 120.4(5) . . ?
C10 C10 C9 125.2(8) 3_466 . ?
C4 C6 C8 120.3(5) . . ?
C8 C7 C2 119.6(5) . . ?
O5 C9 C10 105.9(5) . . ?
C19 C18 N3 109.3(6) . . ?
C18 C19 N4 106.9(6) . . ?
N1 C13 N2 111.1(6) . . ?
N3 C20 N4 111.2(6) . . ?
C12 C11 N1 109.0(6) . . ?
C24 C22 C21 120.4(7) . . ?
C23 C22 C21 121.2(7) . . ?
C23 C22 C24 118.4(7) . . ?
N4 C21 C22 111.2(6) . . ?
C22 C24 C23 121.0(7) . 3_767 ?
C11 C12 N2 106.5(6) . . ?
C22 C23 C24 120.6(7) . 3_767 ?
C17 C15 C14 122.2(8) . . ?
C16 C15 C14 119.6(9) . . ?
C16 C15 C17 118.0(8) . . ?
N2 C14 C15 108.5(7) . . ?
C15 C17 C16 122.4(8) . 3_756 ?
C15 C16 C17 119.7(9) . 3_756 ?

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
O6 H6A O2 0.85 2.02 2.797(8) 150.7 .
O6 H6B O7A 0.85 2.21 2.82(3) 129.0 4_566
O7 H7B O4 0.85 2.01 2.84(2) 163.7 .
O7A H7AB O4 0.85 2.00 2.68(2) 136.3 .

####################################################################### 
# 
# 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_cd091
_database_code_depnum_ccdc_archive 'CCDC 1967444'
loop_
_audit_author_name
_audit_author_address
'Hakan Erer'
;Eskisehir Osmangazi University
Turkey
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2019-11-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5457)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N4 O5 Zn, H2 O'
_chemical_formula_sum            'C24 H22 N4 O6 Zn'
_chemical_formula_weight         527.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.1281(5)
_cell_length_b                   16.1955(12)
_cell_length_c                   17.1781(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.562(2)
_cell_angle_gamma                90
_cell_volume                     2246.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      3.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43678
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.434
_diffrn_reflns_theta_min         2.911
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3920
_reflns_number_total             4587
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         1.359
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.123
_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)+(0.0303P)²+7.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C21(H21A,H21B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C5(H5), C23(H23), C24(H24), C13(H13), C11(H11), C20(H20),
 C16(H16), C10(H10), C12(H12), C18(H18), C22(H22), C17(H17)
;
_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 0.61077(5) 0.69145(2) 0.71579(2) 0.02149(12) Uani 1 1 d . . . . .
O1 O 0.4375(3) 0.68825(17) 0.62824(14) 0.0307(6) Uani 1 1 d . . . . .
O3 O 0.0327(3) 0.73952(17) 0.29799(15) 0.0345(6) Uani 1 1 d . . . . .
O5 O -0.2322(3) 0.56974(18) 0.48605(17) 0.0370(6) Uani 1 1 d . . . . .
O4 O 0.2899(3) 0.75991(19) 0.34982(16) 0.0415(7) Uani 1 1 d . . . . .
N1 N 0.7160(4) 0.58244(18) 0.74644(17) 0.0282(7) Uani 1 1 d . . . . .
N4 N 1.2804(4) 0.74709(18) 1.15768(17) 0.0259(6) Uani 1 1 d . . . . .
O2 O 0.2816(4) 0.6030(2) 0.68944(16) 0.0455(8) Uani 1 1 d . . . . .
N2 N 0.9177(4) 0.49219(18) 0.76671(18) 0.0288(7) Uani 1 1 d . . . . .
N3 N 1.3777(4) 0.6817(2) 1.0603(2) 0.0344(7) Uani 1 1 d . . . . .
C3 C 0.0345(4) 0.6049(2) 0.55909(19) 0.0216(7) Uani 1 1 d . . . . .
H3 H 0.0092 0.5774 0.6037 0.026 Uiso 1 1 calc R . . . .
C2 C 0.1853(4) 0.6451(2) 0.55919(18) 0.0203(7) Uani 1 1 d . . . . .
C6 C 0.1102(4) 0.6861(2) 0.42521(18) 0.0212(7) Uani 1 1 d . . . . .
C7 C 0.2231(4) 0.6859(2) 0.49250(19) 0.0222(7) Uani 1 1 d . . . . .
H7 H 0.3239 0.7132 0.4928 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3079(4) 0.6441(2) 0.63223(19) 0.0243(7) Uani 1 1 d . . . . .
C4 C -0.0791(4) 0.6059(2) 0.4917(2) 0.0231(7) Uani 1 1 d . . . . .
C8 C 0.1504(4) 0.7316(2) 0.3537(2) 0.0257(7) Uani 1 1 d . . . . .
C5 C -0.0408(4) 0.6460(2) 0.42465(19) 0.0238(7) Uani 1 1 d . . . . .
H5 H -0.1159 0.6460 0.3796 0.029 Uiso 1 1 calc R . . . .
C23 C 1.4366(5) 0.7178(2) 1.1829(2) 0.0343(9) Uani 1 1 d . . . . .
H23 H 1.4918 0.7247 1.2330 0.041 Uiso 1 1 calc R . . . .
C24 C 1.2506(4) 0.7244(2) 1.0832(2) 0.0302(8) Uani 1 1 d . . . . .
H24 H 1.1538 0.7366 1.0510 0.036 Uiso 1 1 calc R . . . .
C13 C 0.8786(5) 0.5722(2) 0.7593(2) 0.0343(9) Uani 1 1 d . . . . .
H13 H 0.9553 0.6151 0.7628 0.041 Uiso 1 1 calc R . . . .
C11 C 0.6496(5) 0.5045(2) 0.7456(2) 0.0350(9) Uani 1 1 d . . . . .
H11 H 0.5372 0.4922 0.7375 0.042 Uiso 1 1 calc R . . . .
C20 C 1.2375(5) 0.5484(2) 0.8889(2) 0.0314(8) Uani 1 1 d . . . . .
H20 H 1.2566 0.5853 0.8494 0.038 Uiso 1 1 calc R . . . .
C15 C 1.1529(4) 0.4753(2) 0.8695(2) 0.0285(8) Uani 1 1 d . . . . .
C19 C 1.2940(5) 0.5671(2) 0.9660(2) 0.0313(8) Uani 1 1 d . . . . .
C16 C 1.1274(5) 0.4196(2) 0.9284(2) 0.0344(9) Uani 1 1 d . . . . .
H16 H 1.0724 0.3702 0.9159 0.041 Uiso 1 1 calc R . . . .
C10 C -0.4601(5) 0.4986(3) 0.5339(2) 0.0365(9) Uani 1 1 d . . . . .
H10 H -0.5103 0.4750 0.5745 0.044 Uiso 1 1 calc R . . . .
C12 C 0.7725(5) 0.4486(2) 0.7583(2) 0.0369(9) Uani 1 1 d . . . . .
H12 H 0.7609 0.3916 0.7609 0.044 Uiso 1 1 calc R . . . .
C14 C 1.0860(5) 0.4584(2) 0.7851(2) 0.0343(9) Uani 1 1 d . . . . .
H14A H 1.1588 0.4832 0.7506 0.041 Uiso 1 1 calc R . . . .
H14B H 1.0839 0.3993 0.7758 0.041 Uiso 1 1 calc R . . . .
C18 C 1.2674(5) 0.5111(3) 1.0246(2) 0.0376(9) Uani 1 1 d . . . . .
H18 H 1.3055 0.5229 1.0765 0.045 Uiso 1 1 calc R . . . .
C22 C 1.4968(5) 0.6775(3) 1.1235(3) 0.0399(10) Uani 1 1 d . . . . .
H22 H 1.5994 0.6518 1.1250 0.048 Uiso 1 1 calc R . . . .
C17 C 1.1840(5) 0.4377(3) 1.0058(2) 0.0395(9) Uani 1 1 d . . . . .
H17 H 1.1660 0.4005 1.0452 0.047 Uiso 1 1 calc R . . . .
C21 C 1.3874(6) 0.6474(3) 0.9818(3) 0.0416(10) Uani 1 1 d . . . . .
H21A H 1.5029 0.6383 0.9752 0.050 Uiso 1 1 calc R . . . .
H21B H 1.3440 0.6878 0.9431 0.050 Uiso 1 1 calc R . . . .
C9 C -0.2835(5) 0.5326(3) 0.5512(2) 0.0390(9) Uani 1 1 d . . . . .
H9A H -0.2799 0.5725 0.5935 0.047 Uiso 1 1 calc R . . . .
H9B H -0.2085 0.4879 0.5681 0.047 Uiso 1 1 calc R . . . .
O6 O 0.5986(7) 0.7195(5) 0.4035(5) 0.135(2) Uani 1 1 d . . . . .
H6A H 0.6097 0.6712 0.4227 0.203 Uiso 1 1 d G . . . .
H6B H 0.4980 0.7273 0.3853 0.203 Uiso 1 1 d G . . . .


_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 1.940(2) . ?
Zn1 O3 1.963(3) 4_676 ?
Zn1 N1 2.006(3) . ?
Zn1 N4 2.050(3) 4_575 ?
O1 C1 1.281(4) . ?
O3 Zn1 1.963(3) 4_575 ?
O3 C8 1.281(4) . ?
O5 C4 1.369(4) . ?
O5 C9 1.376(5) . ?
O4 C8 1.232(4) . ?
N1 C13 1.325(5) . ?
N1 C11 1.372(5) . ?
N4 Zn1 2.050(3) 4_676 ?
N4 C23 1.378(5) . ?
N4 C24 1.327(5) . ?
O2 C1 1.226(4) . ?
N2 C13 1.337(5) . ?
N2 C12 1.368(5) . ?
N2 C14 1.474(5) . ?
N3 C24 1.338(5) . ?
N3 C22 1.371(5) . ?
N3 C21 1.468(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.388(5) . ?
C3 C4 1.395(4) . ?
C2 C7 1.388(5) . ?
C2 C1 1.510(4) . ?
C6 C7 1.391(4) . ?
C6 C8 1.500(5) . ?
C6 C5 1.387(5) . ?
C7 H7 0.9300 . ?
C4 C5 1.389(5) . ?
C5 H5 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.350(6) . ?
C24 H24 0.9300 . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.347(6) . ?
C20 H20 0.9300 . ?
C20 C15 1.390(5) . ?
C20 C19 1.385(5) . ?
C15 C16 1.387(5) . ?
C15 C14 1.515(5) . ?
C19 C18 1.389(6) . ?
C19 C21 1.515(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(6) . ?
C10 C10 1.266(8) 3_466 ?
C10 H10 0.9300 . ?
C10 C9 1.535(6) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C17 1.389(6) . ?
C22 H22 0.9300 . ?
C17 H17 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8501 . ?

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 O3 107.88(11) . 4_676 ?
O1 Zn1 N1 115.47(12) . . ?
O1 Zn1 N4 96.01(11) . 4_575 ?
O3 Zn1 N1 118.41(12) 4_676 . ?
O3 Zn1 N4 111.38(12) 4_676 4_575 ?
N1 Zn1 N4 105.37(12) . 4_575 ?
C1 O1 Zn1 120.1(2) . . ?
C8 O3 Zn1 108.6(2) . 4_575 ?
C4 O5 C9 119.1(3) . . ?
C13 N1 Zn1 122.7(3) . . ?
C13 N1 C11 105.7(3) . . ?
C11 N1 Zn1 130.7(3) . . ?
C23 N4 Zn1 131.3(3) . 4_676 ?
C24 N4 Zn1 123.1(2) . 4_676 ?
C24 N4 C23 105.5(3) . . ?
C13 N2 C12 107.3(3) . . ?
C13 N2 C14 125.8(3) . . ?
C12 N2 C14 126.8(3) . . ?
C24 N3 C22 107.0(3) . . ?
C24 N3 C21 126.1(4) . . ?
C22 N3 C21 126.9(3) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 120.2(3) . . ?
C7 C6 C8 119.8(3) . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 C8 120.0(3) . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O1 C1 C2 114.7(3) . . ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 120.8(3) . . ?
O5 C4 C3 124.4(3) . . ?
O5 C4 C5 115.4(3) . . ?
C5 C4 C3 120.2(3) . . ?
O3 C8 C6 116.5(3) . . ?
O4 C8 O3 122.4(3) . . ?
O4 C8 C6 121.0(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N4 C23 H23 125.4 . . ?
C22 C23 N4 109.2(4) . . ?
C22 C23 H23 125.4 . . ?
N4 C24 N3 111.4(3) . . ?
N4 C24 H24 124.3 . . ?
N3 C24 H24 124.3 . . ?
N1 C13 N2 111.0(3) . . ?
N1 C13 H13 124.5 . . ?
N2 C13 H13 124.5 . . ?
N1 C11 H11 125.3 . . ?
C12 C11 N1 109.5(4) . . ?
C12 C11 H11 125.3 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C15 121.0(4) . . ?
C20 C15 C14 119.7(3) . . ?
C16 C15 C20 119.3(4) . . ?
C16 C15 C14 120.9(3) . . ?
C20 C19 C18 119.2(4) . . ?
C20 C19 C21 117.6(4) . . ?
C18 C19 C21 123.1(4) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C10 C10 H10 118.8 3_466 . ?
C10 C10 C9 122.3(5) 3_466 . ?
C9 C10 H10 118.8 . . ?
N2 C12 H12 126.7 . . ?
C11 C12 N2 106.6(3) . . ?
C11 C12 H12 126.7 . . ?
N2 C14 C15 111.1(3) . . ?
N2 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
N3 C22 H22 126.6 . . ?
C23 C22 N3 106.9(3) . . ?
C23 C22 H22 126.6 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
N3 C21 C19 114.3(3) . . ?
N3 C21 H21A 108.7 . . ?
N3 C21 H21B 108.7 . . ?
C19 C21 H21A 108.7 . . ?
C19 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
O5 C9 C10 111.3(3) . . ?
O5 C9 H9A 109.4 . . ?
O5 C9 H9B 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
H6A O6 H6B 109.5 . . ?

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
O6 H6B O4 0.85 1.81 2.654(6) 171.4 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 1.2(5) . . . . ?
Zn1 O1 C1 C2 -178.2(2) . . . . ?
Zn1 O3 C8 O4 -4.3(5) 4_575 . . . ?
Zn1 O3 C8 C6 175.3(2) 4_575 . . . ?
Zn1 N1 C13 N2 -170.3(2) . . . . ?
Zn1 N1 C11 C12 169.4(3) . . . . ?
Zn1 N4 C23 C22 176.8(3) 4_676 . . . ?
Zn1 N4 C24 N3 -176.9(2) 4_676 . . . ?
O5 C4 C5 C6 178.6(3) . . . . ?
N1 C11 C12 N2 -0.4(5) . . . . ?
N4 C23 C22 N3 0.2(5) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
C3 C2 C1 O1 -174.8(3) . . . . ?
C3 C2 C1 O2 5.8(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C2 C3 C4 O5 -178.6(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C7 C2 C1 O1 5.1(5) . . . . ?
C7 C2 C1 O2 -174.3(4) . . . . ?
C7 C6 C8 O3 -170.2(3) . . . . ?
C7 C6 C8 O4 9.5(5) . . . . ?
C7 C6 C5 C4 0.2(5) . . . . ?
C1 C2 C7 C6 179.6(3) . . . . ?
C4 O5 C9 C10 177.9(3) . . . . ?
C4 C3 C2 C7 -0.1(5) . . . . ?
C4 C3 C2 C1 179.8(3) . . . . ?
C8 C6 C7 C2 178.9(3) . . . . ?
C8 C6 C5 C4 -178.2(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C6 C8 O3 8.3(5) . . . . ?
C5 C6 C8 O4 -172.0(3) . . . . ?
C23 N4 C24 N3 0.8(4) . . . . ?
C24 N4 C23 C22 -0.6(4) . . . . ?
C24 N3 C22 C23 0.3(5) . . . . ?
C24 N3 C21 C19 -79.5(5) . . . . ?
C13 N1 C11 C12 0.3(5) . . . . ?
C13 N2 C12 C11 0.3(5) . . . . ?
C13 N2 C14 C15 71.6(5) . . . . ?
C11 N1 C13 N2 -0.1(4) . . . . ?
C20 C15 C16 C17 0.9(6) . . . . ?
C20 C15 C14 N2 -88.5(4) . . . . ?
C20 C19 C18 C17 -0.5(6) . . . . ?
C20 C19 C21 N3 153.6(4) . . . . ?
C15 C20 C19 C18 1.0(6) . . . . ?
C15 C20 C19 C21 179.1(3) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C19 C20 C15 C16 -1.2(6) . . . . ?
C19 C20 C15 C14 177.2(3) . . . . ?
C19 C18 C17 C16 0.3(6) . . . . ?
C16 C15 C14 N2 89.9(4) . . . . ?
C10 C10 C9 O5 3.8(7) 3_466 . . . ?
C12 N2 C13 N1 -0.2(5) . . . . ?
C12 N2 C14 C15 -104.6(4) . . . . ?
C14 N2 C13 N1 -177.0(3) . . . . ?
C14 N2 C12 C11 177.1(3) . . . . ?
C14 C15 C16 C17 -177.5(4) . . . . ?
C18 C19 C21 N3 -28.4(6) . . . . ?
C22 N3 C24 N4 -0.7(4) . . . . ?
C22 N3 C21 C19 101.6(5) . . . . ?
C21 N3 C24 N4 -179.8(3) . . . . ?
C21 N3 C22 C23 179.4(4) . . . . ?
C21 C19 C18 C17 -178.5(4) . . . . ?
C9 O5 C4 C3 3.0(5) . . . . ?
C9 O5 C4 C5 -176.5(3) . . . . ?

