# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DCF-10
_database_code_depnum_ccdc_archive 'CCDC 2195444'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Fu'
;Luoyang Normal University
China
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2022-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N5 O2 Zn'
_chemical_formula_sum            'C8 H9 N5 O2 Zn'
_chemical_formula_weight         272.59
_chemical_absolute_configuration ad
_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'
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'
H H 0.0000 0.0000 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7893(5)
_cell_length_b                   10.0252(7)
_cell_length_c                   10.2988(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1010.72(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1644
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9490
_cell_measurement_theta_min      4.4420
_shelx_estimated_absorpt_T_max   0.794
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3248
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_min         3.518
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -13.00   1.00    2.05    --  -15.84 -38.00-150.00   33
  2  ω      0.00  69.00   1.00    2.05    --   17.09  57.00-180.00   69
  3  ω     -9.00  33.00   1.00    2.05    --   17.09  77.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150176000
_diffrn_orient_matrix_UB_12      0.0682924000
_diffrn_orient_matrix_UB_13      0.0110085000
_diffrn_orient_matrix_UB_21      0.0029826000
_diffrn_orient_matrix_UB_22      -0.0122471000
_diffrn_orient_matrix_UB_23      0.0677869000
_diffrn_orient_matrix_UB_31      0.0707945000
_diffrn_orient_matrix_UB_32      -0.0139782000
_diffrn_orient_matrix_UB_33      -0.0052247000
_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         0.552
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                1993
_reflns_number_total             2136
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.061
_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)+(0.0217P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0631
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_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 0.43679(4) 0.21302(5) 0.34701(4) 0.02233(14) Uani 1 1 d . . . . .
O1 O 0.5183(3) 0.4064(3) 0.2954(3) 0.0278(7) Uani 1 1 d . . . . .
O2 O 0.6253(3) 0.5118(3) 0.1336(3) 0.0310(8) Uani 1 1 d . . . . .
N1 N 0.2504(3) 0.2855(5) 0.3880(3) 0.0237(8) Uani 1 1 d . . . . .
N3 N 0.0623(4) 0.3089(4) 0.4989(3) 0.0253(8) Uani 1 1 d . . . . .
N0AA N 0.1868(4) 0.2556(4) 0.4995(4) 0.0259(8) Uani 1 1 d . . . . .
N2 N 0.1904(4) 0.4078(4) 0.1942(3) 0.0322(10) Uani 1 1 d . . . . .
N4 N 0.4740(4) 0.1913(4) 0.1531(4) 0.0360(9) Uani 1 1 d . . . . .
H4A H 0.4969 0.1071 0.1367 0.043 Uiso 1 1 calc R . . . .
H4B H 0.3983 0.2097 0.1087 0.043 Uiso 1 1 calc R . . . .
C5 C 0.5745(4) 0.4108(4) 0.1859(4) 0.0242(9) Uani 1 1 d . . . . .
C1AA C -0.0628(5) 0.4488(4) 0.3312(4) 0.0331(11) Uani 1 1 d . . . . .
H1AA H -0.1452 0.4611 0.3745 0.040 Uiso 1 1 calc R . . . .
C1 C 0.1646(4) 0.3608(4) 0.3141(4) 0.0230(10) Uani 1 1 d . . . . .
C6 C 0.5851(5) 0.2805(5) 0.1094(4) 0.0302(10) Uani 1 1 d . . . . .
H6 H 0.5752 0.2987 0.0164 0.036 Uiso 1 1 calc R . . . .
C0AA C 0.0444(4) 0.3759(4) 0.3839(4) 0.0244(10) Uani 1 1 d . . . . .
C7 C 0.7216(5) 0.2167(6) 0.1349(5) 0.0459(13) Uani 1 1 d . . . . .
H7A H 0.7319 0.2012 0.2264 0.069 Uiso 1 1 calc GR . . . .
H7B H 0.7930 0.2749 0.1054 0.069 Uiso 1 1 calc GR . . . .
H7C H 0.7270 0.1334 0.0894 0.069 Uiso 1 1 calc GR . . . .
C3 C 0.0867(5) 0.4793(5) 0.1473(5) 0.0369(12) Uani 1 1 d . . . . .
H3 H 0.0979 0.5178 0.0658 0.044 Uiso 1 1 calc R . . . .
C4 C -0.0380(5) 0.5010(5) 0.2111(4) 0.0386(12) Uani 1 1 d . . . . .
H4 H -0.1051 0.5519 0.1707 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.163(3) . ?
Zn1 O2 2.116(3) 3_645 ?
Zn1 N1 2.008(3) . ?
Zn1 N3 2.019(3) 4_556 ?
Zn1 N4 2.042(4) . ?
O1 C5 1.256(5) . ?
O2 Zn1 2.116(3) 3_655 ?
O2 C5 1.250(5) . ?
N1 N0AA 1.340(5) . ?
N1 C1 1.362(5) . ?
N3 Zn1 2.019(3) 4_456 ?
N3 N0AA 1.331(5) . ?
N3 C0AA 1.373(5) . ?
N2 C1 1.345(5) . ?
N2 C3 1.334(6) . ?
N4 C6 1.478(5) . ?
C5 C6 1.529(6) . ?
C1AA C0AA 1.389(6) . ?
C1AA C4 1.365(6) . ?
C1 C0AA 1.387(6) . ?
C6 C7 1.504(6) . ?
C3 C4 1.403(6) . ?

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 O1 169.64(11) 3_645 . ?
N1 Zn1 O1 93.57(15) . . ?
N1 Zn1 O2 93.66(15) . 3_645 ?
N1 Zn1 N3 115.27(13) . 4_556 ?
N1 Zn1 N4 113.97(15) . . ?
N3 Zn1 O1 93.80(13) 4_556 . ?
N3 Zn1 O2 89.80(13) 4_556 3_645 ?
N3 Zn1 N4 130.44(16) 4_556 . ?
N4 Zn1 O1 77.85(12) . . ?
N4 Zn1 O2 92.42(13) . 3_645 ?
C5 O1 Zn1 114.4(3) . . ?
C5 O2 Zn1 128.1(3) . 3_655 ?
N0AA N1 Zn1 121.4(3) . . ?
N0AA N1 C1 108.4(3) . . ?
C1 N1 Zn1 130.1(3) . . ?
N0AA N3 Zn1 120.7(3) . 4_456 ?
N0AA N3 C0AA 108.5(3) . . ?
C0AA N3 Zn1 130.9(3) . 4_456 ?
N3 N0AA N1 109.4(3) . . ?
C3 N2 C1 112.2(4) . . ?
C6 N4 Zn1 111.4(3) . . ?
O1 C5 C6 117.5(4) . . ?
O2 C5 O1 126.2(4) . . ?
O2 C5 C6 116.3(4) . . ?
C4 C1AA C0AA 114.9(4) . . ?
N1 C1 C0AA 107.1(3) . . ?
N2 C1 N1 126.2(4) . . ?
N2 C1 C0AA 126.6(4) . . ?
N4 C6 C5 108.1(3) . . ?
N4 C6 C7 110.1(4) . . ?
C7 C6 C5 109.4(4) . . ?
N3 C0AA C1AA 133.7(4) . . ?
N3 C0AA C1 106.6(4) . . ?
C1 C0AA C1AA 119.7(4) . . ?
N2 C3 C4 125.1(5) . . ?
C1AA C4 C3 121.3(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C5 O2 177.8(3) . . . . ?
Zn1 O1 C5 C6 -3.5(5) . . . . ?
Zn1 O2 C5 O1 -31.5(6) 3_655 . . . ?
Zn1 O2 C5 C6 149.7(3) 3_655 . . . ?
Zn1 N1 N0AA N3 -176.1(3) . . . . ?
Zn1 N1 C1 N2 -2.4(7) . . . . ?
Zn1 N1 C1 C0AA 175.7(3) . . . . ?
Zn1 N3 N0AA N1 -179.1(3) 4_456 . . . ?
Zn1 N3 C0AA C1AA -1.3(8) 4_456 . . . ?
Zn1 N3 C0AA C1 178.7(3) 4_456 . . . ?
Zn1 N4 C6 C5 -35.6(4) . . . . ?
Zn1 N4 C6 C7 83.9(4) . . . . ?
O1 C5 C6 N4 25.5(5) . . . . ?
O1 C5 C6 C7 -94.4(5) . . . . ?
O2 C5 C6 N4 -155.6(4) . . . . ?
O2 C5 C6 C7 84.5(5) . . . . ?
N1 C1 C0AA N3 0.2(5) . . . . ?
N1 C1 C0AA C1AA -179.8(4) . . . . ?
N0AA N1 C1 N2 -178.4(4) . . . . ?
N0AA N1 C1 C0AA -0.3(5) . . . . ?
N0AA N3 C0AA C1AA 179.9(5) . . . . ?
N0AA N3 C0AA C1 0.0(5) . . . . ?
N2 C1 C0AA N3 178.3(4) . . . . ?
N2 C1 C0AA C1AA -1.7(7) . . . . ?
N2 C3 C4 C1AA 0.4(8) . . . . ?
C1 N1 N0AA N3 0.3(5) . . . . ?
C1 N2 C3 C4 -2.1(7) . . . . ?
C0AA N3 N0AA N1 -0.2(5) . . . . ?
C0AA C1AA C4 C3 0.9(7) . . . . ?
C3 N2 C1 N1 -179.5(4) . . . . ?
C3 N2 C1 C0AA 2.8(7) . . . . ?
C4 C1AA C0AA N3 179.8(5) . . . . ?
C4 C1AA C0AA C1 -0.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_TrzPy_auto
_database_code_depnum_ccdc_archive 'CCDC 2195443'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Fu'
;Luoyang Normal University
China
;
_audit_update_record             
;
2022-08-11 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        TrzPy
_chemical_formula_moiety         'C5 H4 N4'
_chemical_formula_sum            'C5 H4 N4'
_chemical_formula_weight         120.12
_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'

_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                   3.7561(4)
_cell_length_b                   10.2354(13)
_cell_length_c                   14.2732(16)
_cell_angle_alpha                97.137(10)
_cell_angle_beta                 96.109(9)
_cell_angle_gamma                92.497(9)
_cell_volume                     540.49(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    824
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1910
_cell_measurement_theta_min      4.4320
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4445
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.208
_diffrn_reflns_theta_min         3.303
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  41.00   1.00   10.00    --   16.93  77.00 120.00   51
  2  ω    -42.00  44.00   1.00   10.00    --   16.93 -77.00 -90.00   86
  3  ω     -9.00  39.00   1.00   10.00    --   16.93  77.00  30.00   48
  4  ω     63.00  89.00   1.00   10.00    --   16.93 178.00 -90.00   26
  5  ω    -10.00  17.00   1.00   10.00    --   16.93 -99.00  60.00   27
  6  ω    -52.00  73.00   1.00   10.00    --   16.93   0.00  90.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0692221000
_diffrn_orient_matrix_UB_12      -0.0397489000
_diffrn_orient_matrix_UB_13      -0.0374152000
_diffrn_orient_matrix_UB_21      0.0240457000
_diffrn_orient_matrix_UB_22      -0.0508408000
_diffrn_orient_matrix_UB_23      0.0292356000
_diffrn_orient_matrix_UB_31      -0.1755549000
_diffrn_orient_matrix_UB_32      -0.0270006000
_diffrn_orient_matrix_UB_33      -0.0169107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                1255
_reflns_number_total             2438
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1484
_refine_ls_R_factor_gt           0.0746
_refine_ls_restrained_S_all      1.095
_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)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1705
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), N4(H4), C3(H3), C2(H2), C1(H1), C6(H6), C8(H8A), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 1.0585(6) 0.1431(2) 0.34527(19) 0.0468(7) Uani 1 1 d . . . . .
N8 N 0.3578(6) 0.8983(3) 0.29521(18) 0.0498(7) Uani 1 1 d . . . . .
H8 H 0.292151 0.977112 0.309443 0.060 Uiso 1 1 calc R U . . .
N4 N 0.8923(6) 0.3942(3) 0.20797(18) 0.0489(7) Uani 1 1 d . . . . .
H4 H 0.826805 0.470270 0.195674 0.059 Uiso 1 1 calc R U . . .
N5 N 0.6496(6) 0.6340(2) 0.15287(19) 0.0509(7) Uani 1 1 d . . . . .
N2 N 1.0902(6) 0.1982(3) 0.18623(19) 0.0497(7) Uani 1 1 d . . . . .
N3 N 1.0124(7) 0.3023(3) 0.14508(19) 0.0554(8) Uani 1 1 d . . . . .
N6 N 0.4910(7) 0.6977(3) 0.31158(19) 0.0581(8) Uani 1 1 d . . . . .
N7 N 0.3792(7) 0.8065(3) 0.35454(19) 0.0579(8) Uani 1 1 d . . . . .
C4 C 1.0149(7) 0.2250(3) 0.2785(2) 0.0390(7) Uani 1 1 d . . . . .
C5 C 0.8891(7) 0.3498(3) 0.2936(2) 0.0377(7) Uani 1 1 d . . . . .
C9 C 0.5388(7) 0.7216(3) 0.2214(2) 0.0421(8) Uani 1 1 d . . . . .
C10 C 0.4548(7) 0.8490(3) 0.2093(2) 0.0387(7) Uani 1 1 d . . . . .
C3 C 0.9673(8) 0.1937(3) 0.4297(2) 0.0518(9) Uani 1 1 d . . . . .
H3 H 0.991815 0.141936 0.478894 0.062 Uiso 1 1 calc R U . . .
C2 C 0.8372(8) 0.3194(3) 0.4494(2) 0.0493(8) Uani 1 1 d . . . . .
H2 H 0.778279 0.347411 0.510058 0.059 Uiso 1 1 calc R U . . .
C1 C 0.7958(7) 0.4010(3) 0.3811(2) 0.0476(8) Uani 1 1 d . . . . .
H1 H 0.711017 0.484814 0.392574 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4831(8) 0.8968(3) 0.1242(2) 0.0501(8) Uani 1 1 d . . . . .
H6 H 0.431772 0.982554 0.114741 0.060 Uiso 1 1 calc R U . . .
C8 C 0.6715(8) 0.6811(3) 0.0713(2) 0.0537(9) Uani 1 1 d . . . . .
H8A H 0.744968 0.625229 0.021373 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5923(8) 0.8085(3) 0.0549(2) 0.0546(9) Uani 1 1 d . . . . .
H7 H 0.614274 0.834008 -0.004584 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.347(4) . ?
N1 C3 1.337(4) . ?
N8 H8 0.8600 . ?
N8 N7 1.341(3) . ?
N8 C10 1.359(3) . ?
N4 H4 0.8600 . ?
N4 N3 1.344(3) . ?
N4 C5 1.357(3) . ?
N5 C9 1.354(4) . ?
N5 C8 1.324(4) . ?
N2 N3 1.309(3) . ?
N2 C4 1.373(3) . ?
N6 N7 1.310(3) . ?
N6 C9 1.369(4) . ?
C4 C5 1.381(4) . ?
C5 C1 1.380(4) . ?
C9 C10 1.382(4) . ?
C10 C6 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.402(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.361(4) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.363(4) . ?
C8 H8A 0.9300 . ?
C8 C7 1.392(4) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 113.6(3) . . ?
N7 N8 H8 124.9 . . ?
N7 N8 C10 110.2(3) . . ?
C10 N8 H8 124.9 . . ?
N3 N4 H4 124.8 . . ?
N3 N4 C5 110.4(3) . . ?
C5 N4 H4 124.8 . . ?
C8 N5 C9 113.8(3) . . ?
N3 N2 C4 106.6(3) . . ?
N2 N3 N4 109.6(3) . . ?
N7 N6 C9 106.4(3) . . ?
N6 N7 N8 109.8(3) . . ?
N1 C4 N2 125.6(3) . . ?
N1 C4 C5 124.5(3) . . ?
N2 C4 C5 109.9(3) . . ?
N4 C5 C4 103.6(3) . . ?
N4 C5 C1 135.1(3) . . ?
C1 C5 C4 121.4(3) . . ?
N5 C9 N6 125.6(3) . . ?
N5 C9 C10 124.3(3) . . ?
N6 C9 C10 110.1(3) . . ?
N8 C10 C9 103.5(3) . . ?
N8 C10 C6 135.5(3) . . ?
C6 C10 C9 121.0(3) . . ?
N1 C3 H3 117.7 . . ?
N1 C3 C2 124.6(3) . . ?
C2 C3 H3 117.7 . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C5 C1 H1 122.5 . . ?
C2 C1 C5 114.9(3) . . ?
C2 C1 H1 122.5 . . ?
C10 C6 H6 122.6 . . ?
C7 C6 C10 114.8(3) . . ?
C7 C6 H6 122.6 . . ?
N5 C8 H8A 117.7 . . ?
N5 C8 C7 124.5(3) . . ?
C7 C8 H8A 117.7 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?

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
N1 C4 C5 N4 179.8(3) . . . . ?
N1 C4 C5 C1 -0.1(4) . . . . ?
N1 C3 C2 C1 -0.3(5) . . . . ?
N8 C10 C6 C7 -179.5(3) . . . . ?
N4 C5 C1 C2 -179.9(3) . . . . ?
N5 C9 C10 N8 179.7(3) . . . . ?
N5 C9 C10 C6 -0.7(4) . . . . ?
N5 C8 C7 C6 0.1(5) . . . . ?
N2 C4 C5 N4 0.2(3) . . . . ?
N2 C4 C5 C1 -179.6(2) . . . . ?
N3 N4 C5 C4 0.0(3) . . . . ?
N3 N4 C5 C1 179.7(3) . . . . ?
N3 N2 C4 N1 -179.8(3) . . . . ?
N3 N2 C4 C5 -0.3(3) . . . . ?
N6 C9 C10 N8 0.1(3) . . . . ?
N6 C9 C10 C6 179.7(3) . . . . ?
N7 N8 C10 C9 -0.5(3) . . . . ?
N7 N8 C10 C6 180.0(3) . . . . ?
N7 N6 C9 N5 -179.3(3) . . . . ?
N7 N6 C9 C10 0.3(3) . . . . ?
C4 N1 C3 C2 0.1(4) . . . . ?
C4 N2 N3 N4 0.3(3) . . . . ?
C4 C5 C1 C2 -0.1(4) . . . . ?
C5 N4 N3 N2 -0.1(3) . . . . ?
C9 N5 C8 C7 0.4(4) . . . . ?
C9 N6 N7 N8 -0.6(3) . . . . ?
C9 C10 C6 C7 1.0(4) . . . . ?
C10 N8 N7 N6 0.7(3) . . . . ?
C10 C6 C7 C8 -0.8(4) . . . . ?
C3 N1 C4 N2 179.5(3) . . . . ?
C3 N1 C4 C5 0.1(4) . . . . ?
C3 C2 C1 C5 0.3(4) . . . . ?
C8 N5 C9 N6 179.5(3) . . . . ?
C8 N5 C9 C10 -0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.633
####################################################################### 
# 
# 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_LCF-10_auto
_database_code_depnum_ccdc_archive 'CCDC 2195445'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Fu'
;Luoyang Normal University
China
;
_audit_update_record             
;
2022-08-11 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        PL134
_chemical_formula_moiety         'C8 H9 N5 O2 Zn'
_chemical_formula_sum            'C8 H9 N5 O2 Zn'
_chemical_formula_weight         272.57
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7703(9)
_cell_length_b                   9.9768(10)
_cell_length_c                   10.6503(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1038.15(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4830
_cell_measurement_theta_min      4.3320
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.650
_exptl_absorpt_coefficient_mu    2.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3276
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.292
_diffrn_reflns_theta_min         3.490
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.859
_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  37.00   1.00    1.93    --   16.93  77.00 -90.00   43
  2  ω     34.00  70.00   1.00    1.93    --   16.93  57.00-150.00   36
  3  ω      2.00  64.00   1.00    1.93    --   16.93  57.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0140471000
_diffrn_orient_matrix_UB_12      0.0183811000
_diffrn_orient_matrix_UB_13      -0.0629437000
_diffrn_orient_matrix_UB_21      0.0135635000
_diffrn_orient_matrix_UB_22      -0.0667405000
_diffrn_orient_matrix_UB_23      -0.0195520000
_diffrn_orient_matrix_UB_31      -0.0699100000
_diffrn_orient_matrix_UB_32      -0.0166732000
_diffrn_orient_matrix_UB_33      0.0088840000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.514
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                1999
_reflns_number_total             2125
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.061
_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)+(0.0278P)²+0.0397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0724
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C2(H2)
2.c X=CH2 refined with riding coordinates:
 N5(H5a,H5b)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c)
;
_atom_sites_solution_hydrogens   geom
_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 0.54939(5) 0.20600(5) 0.35254(4) 0.02259(15) Uani 1 1 d . . . . .
O2 O 0.5083(4) 0.5113(3) 0.0905(3) 0.0377(10) Uani 1 1 d . . . . .
O1 O 0.5718(4) 0.3995(3) 0.2634(3) 0.0318(8) Uani 1 1 d . . . . .
N3 N 0.3052(4) 0.2563(4) 0.4987(4) 0.0270(9) Uani 1 1 d . . . . .
N2 N 0.2477(3) 0.3157(4) 0.5966(3) 0.0263(9) Uani 1 1 d . . . . .
N4 N 0.4377(3) 0.2917(4) 0.4911(3) 0.0252(8) Uani 1 1 d . . . . .
C6 C 0.5252(4) 0.4054(5) 0.1535(5) 0.0271(10) Uani 1 1 d . . . . .
N1 N 0.3250(4) 0.4648(5) 0.7595(4) 0.0369(11) Uani 1 1 d . . . . .
C5 C 0.3436(4) 0.3921(5) 0.6554(5) 0.0243(9) Uani 1 1 d . . . . .
C4 C 0.4647(5) 0.3782(5) 0.5875(4) 0.0250(10) Uani 1 1 d . . . . .
C7 C 0.4820(4) 0.2744(5) 0.0893(4) 0.0290(11) Uani 1 1 d . . . . .
H7 H 0.521557 0.271122 0.004837 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5825(5) 0.4462(5) 0.6286(5) 0.0344(12) Uani 1 1 d . . . . .
H3 H 0.666304 0.439369 0.587743 0.041 Uiso 1 1 calc R U . . .
C1 C 0.4368(7) 0.5296(6) 0.7965(5) 0.0436(14) Uani 1 1 d . . . . .
H1 H 0.430845 0.582362 0.868241 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5639(6) 0.5236(6) 0.7340(5) 0.0465(15) Uani 1 1 d . . . . .
H2 H 0.637029 0.573265 0.764890 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3265(5) 0.2681(6) 0.0796(7) 0.0607(19) Uani 1 1 d . . . . .
H8A H 0.300459 0.189949 0.032744 0.091 Uiso 1 1 calc R U . . .
H8B H 0.293466 0.346844 0.037659 0.091 Uiso 1 1 calc R U . . .
H8C H 0.287717 0.263463 0.162310 0.091 Uiso 1 1 calc R U . . .
N5 N 0.5317(4) 0.1585(4) 0.1625(4) 0.0309(9) Uani 1 1 d . . . . .
H5A H 0.474433 0.100954 0.191702 0.037 Uiso 1 1 calc R U . . .
H5B H 0.617901 0.148552 0.175862 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 2.112(3) 3_645 ?
Zn1 O1 2.163(3) . ?
Zn1 N2 2.023(3) 4_556 ?
Zn1 N4 2.025(3) . ?
Zn1 N5 2.086(4) . ?
O2 C6 1.262(5) . ?
O1 C6 1.256(6) . ?
N3 N2 1.324(5) . ?
N3 N4 1.344(5) . ?
N2 C5 1.360(6) . ?
N4 C4 1.366(5) . ?
C6 C7 1.534(6) . ?
N1 C5 1.338(6) . ?
N1 C1 1.329(7) . ?
C5 C4 1.394(6) . ?
C4 C3 1.406(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.524(6) . ?
C7 N5 1.476(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.374(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.410(7) . ?
C2 H2 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?

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 O1 166.98(13) 3_645 . ?
N2 Zn1 O2 94.60(15) 4_556 3_645 ?
N2 Zn1 O1 96.69(15) 4_556 . ?
N2 Zn1 N4 111.48(14) 4_556 . ?
N2 Zn1 N5 108.36(15) 4_556 . ?
N4 Zn1 O2 92.02(14) . 3_645 ?
N4 Zn1 O1 89.85(14) . . ?
N4 Zn1 N5 139.32(15) . . ?
N5 Zn1 O2 92.73(14) . 3_645 ?
N5 Zn1 O1 77.58(13) . . ?
C6 O2 Zn1 130.7(3) . 3_655 ?
C6 O1 Zn1 114.5(3) . . ?
N2 N3 N4 109.8(4) . . ?
N3 N2 Zn1 124.7(3) . 4_456 ?
N3 N2 C5 108.7(3) . . ?
C5 N2 Zn1 126.6(3) . 4_456 ?
N3 N4 Zn1 116.9(3) . . ?
N3 N4 C4 107.9(4) . . ?
C4 N4 Zn1 135.2(3) . . ?
O2 C6 C7 116.1(4) . . ?
O1 C6 O2 125.6(4) . . ?
O1 C6 C7 118.3(4) . . ?
C1 N1 C5 113.4(4) . . ?
N2 C5 C4 106.9(4) . . ?
N1 C5 N2 126.3(4) . . ?
N1 C5 C4 126.8(4) . . ?
N4 C4 C5 106.8(4) . . ?
N4 C4 C3 134.2(4) . . ?
C5 C4 C3 119.0(4) . . ?
C6 C7 H7 109.2 . . ?
C8 C7 C6 109.8(4) . . ?
C8 C7 H7 109.2 . . ?
N5 C7 C6 110.0(3) . . ?
N5 C7 H7 109.2 . . ?
N5 C7 C8 109.4(5) . . ?
C4 C3 H3 122.7 . . ?
C2 C3 C4 114.7(5) . . ?
C2 C3 H3 122.7 . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.3(4) . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Zn1 N5 H5A 81.6 . . ?
Zn1 N5 H5B 77.5 . . ?
C7 N5 Zn1 111.2(3) . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?

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 O2 C6 O1 -34.8(7) 3_655 . . . ?
Zn1 O2 C6 C7 144.1(3) 3_655 . . . ?
Zn1 O1 C6 O2 168.9(4) . . . . ?
Zn1 O1 C6 C7 -10.0(5) . . . . ?
Zn1 N2 C5 N1 1.5(7) 4_456 . . . ?
Zn1 N2 C5 C4 -179.3(3) 4_456 . . . ?
Zn1 N4 C4 C5 -176.3(3) . . . . ?
Zn1 N4 C4 C3 1.7(9) . . . . ?
O2 C6 C7 C8 -70.6(6) . . . . ?
O2 C6 C7 N5 169.0(4) . . . . ?
O1 C6 C7 C8 108.4(5) . . . . ?
O1 C6 C7 N5 -12.0(6) . . . . ?
N3 N2 C5 N1 -178.4(5) . . . . ?
N3 N2 C5 C4 0.7(5) . . . . ?
N3 N4 C4 C5 1.0(5) . . . . ?
N3 N4 C4 C3 179.0(5) . . . . ?
N2 N3 N4 Zn1 177.3(3) . . . . ?
N2 N3 N4 C4 -0.6(5) . . . . ?
N2 C5 C4 N4 -1.1(5) . . . . ?
N2 C5 C4 C3 -179.4(4) . . . . ?
N4 N3 N2 Zn1 180.0(3) . . . 4_456 ?
N4 N3 N2 C5 -0.1(5) . . . . ?
N4 C4 C3 C2 -178.9(6) . . . . ?
C6 C7 N5 Zn1 28.2(4) . . . . ?
N1 C5 C4 N4 178.1(5) . . . . ?
N1 C5 C4 C3 -0.2(8) . . . . ?
N1 C1 C2 C3 -1.2(10) . . . . ?
C5 N1 C1 C2 -0.2(9) . . . . ?
C5 C4 C3 C2 -1.1(7) . . . . ?
C4 C3 C2 C1 1.8(8) . . . . ?
C1 N1 C5 N2 179.9(5) . . . . ?
C1 N1 C5 C4 0.9(8) . . . . ?
C8 C7 N5 Zn1 -92.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.079
_oxdiff_exptl_absorpt_empirical_full_min 0.939
