# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_laq-20210407
_database_code_depnum_ccdc_archive 'CCDC 2157693'
loop_
_audit_author_name
_audit_author_address
'Xiaopeng Xuan'
;henan normal university
China
;
_audit_update_record             
;
2022-03-10 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2021-04-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C48 H40 N24 O8 Zn4), C3 H7 N O'
_chemical_formula_sum            'C27 H27 N13 O5 Zn2'
_chemical_formula_weight         744.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn1 C1 N1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.6657(3)
_cell_length_b                   11.3205(2)
_cell_length_c                   8.8645(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1772.76(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3310
_cell_measurement_theta_min      6.3310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yelllow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5570
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.552
_diffrn_reflns_theta_min         4.639
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00  -7.00   1.00    1.00    --  -35.62 133.00-140.00   87
  2  ω    -54.00  18.00   1.00    1.00    --  -35.62  62.00 163.00   72
  3  ω    106.00 132.00   1.00    3.17    --  107.12  62.00 163.00   26
  4  ω     41.00 122.00   1.00    3.17    --  107.12 -62.00  25.00   81
  5  ω     90.00 118.00   1.00    3.17    --  107.12 -58.00-154.00   28
  6  ω    106.00 173.00   1.00    3.17    --  107.12  58.00 -13.00   67
  7  ω     44.00 102.00   1.00    3.17    --  107.12-136.00 -26.00   58
  8  ω      1.00  70.00   1.00    1.00    --   35.62 -99.00 150.00   69
  9  ω     36.00  94.00   1.00    1.00    --   35.62  57.00-150.00   58
 10  ω    101.00 177.00   1.00    3.17    --  107.12 111.00 -60.00   76
 11  ω     91.00 172.00   1.00    3.17    --  107.12  45.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061129000
_diffrn_orient_matrix_UB_12      -0.1355396000
_diffrn_orient_matrix_UB_13      0.0098426000
_diffrn_orient_matrix_UB_21      0.0601561000
_diffrn_orient_matrix_UB_22      -0.0122008000
_diffrn_orient_matrix_UB_23      -0.1247868000
_diffrn_orient_matrix_UB_31      0.0627772000
_diffrn_orient_matrix_UB_32      -0.0015317000
_diffrn_orient_matrix_UB_33      0.1206682000
_diffrn_oxdiff_digest_frames     
;
01b45756eacbcdfda39eef6f0ea20d2d2800036a905
;
_diffrn_oxdiff_digest_hkl        
;
01333283307af2f7efd5972a2c719ca95b2f98
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                2665
_reflns_number_total             2800
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         1.106
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     262
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1352P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1713
_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. Restrained distances
 O3-C13 = O4-C17
 1.2 with sigma of 0.01
 O3-N7
 2.2 with sigma of 0.02
 N8-C17 = N7-C13 = N7-C14 = N8-C16 = N8-C18 = N7-C15
 1.48 with sigma of 0.01
 C15-C14 = C16-C18
 2.5 with sigma of 0.02
 C16-C17
 2.5 with sigma of 0.02
 C13-C15
 2.5 with sigma of 0.02
3. Restrained planarity
 C14, N7, C13, C15, O3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C15 \\sim N7 \\sim C13 \\sim C14 \\sim O3: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
N7 \\sim O3 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim N8 \\sim C17 \\sim
C18 \\sim O4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(N7) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(N8) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C15, N7, C13, C14, O3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N7, O3, C13, C14, C15, C16, N8, C17, C18, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(N8)=Sof(C17)=Sof(H17)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(O4)=0.5*(1-FVAR(2))
 Sof(N7)=Sof(O3)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=0.5*FVAR(2)
7.a Rotating group:
 N6(H6A,H6B)
7.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13), 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 0.39350(3) 0.50796(6) 0.9717(4) 0.0291(3) Uani 1 1 d . . . . .
O1 O 0.3338(3) 0.3860(4) 0.8750(6) 0.0439(10) Uani 1 1 d . . . . .
N1 N 0.5634(3) 0.5690(5) 0.6582(7) 0.0370(10) Uani 1 1 d . . . . .
O2 O 0.3048(4) 0.5167(5) 0.6974(8) 0.0492(14) Uani 1 1 d . . . . .
N2 N 0.1717(3) 0.1395(5) 0.5517(6) 0.0359(10) Uani 1 1 d . . . . .
N3 N 0.4788(3) 0.5667(5) 0.8487(6) 0.0370(11) Uani 1 1 d . . . . .
N4 N 0.5308(3) 0.7243(5) 1.0001(7) 0.0434(12) Uani 1 1 d . . . . .
N5 N 0.6409(3) 0.8141(6) 0.8872(8) 0.0475(13) Uani 1 1 d . . . . .
C1 C 0.5307(3) 0.6536(5) 0.8768(7) 0.0342(11) Uani 1 1 d . . . . .
C2 C 0.3003(3) 0.4174(6) 0.7531(8) 0.0398(13) Uani 1 1 d . . . . .
N6 N 0.6955(3) 0.7526(6) 0.6635(9) 0.0519(14) Uani 1 1 d . . . . .
H6A H 0.698504 0.688568 0.611335 0.062 Uiso 1 1 d GR . . . .
H6B H 0.684698 0.810700 0.604544 0.062 Uiso 1 1 d GR . . . .
C3 C 0.5014(5) 0.5200(5) 0.7180(11) 0.0377(14) Uani 1 1 d . . . . .
H3 H 0.475899 0.457875 0.671856 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2574(4) 0.2079(6) 0.7371(8) 0.0449(15) Uani 1 1 d . . . . .
H4 H 0.287060 0.192050 0.821317 0.054 Uiso 1 1 calc R . . . .
C5 C 0.5824(3) 0.6548(6) 0.7603(7) 0.0340(12) Uani 1 1 d . . . . .
C6 C 0.2562(3) 0.3207(5) 0.6776(7) 0.0353(11) Uani 1 1 d . . . . .
C7 C 0.2078(4) 0.4471(6) 0.4755(10) 0.0537(18) Uani 1 1 d . . . . .
H7A H 0.239079 0.503263 0.527518 0.080 Uiso 1 1 calc R . . . .
H7B H 0.225279 0.438738 0.373476 0.080 Uiso 1 1 calc R . . . .
H7C H 0.156366 0.474244 0.475256 0.080 Uiso 1 1 calc R . . . .
C8 C 0.2118(4) 0.3408(6) 0.5467(8) 0.0422(14) Uani 1 1 d . . . . .
C9 C 0.1707(3) 0.2454(5) 0.4904(8) 0.0385(12) Uani 1 1 d . . . . .
H9 H 0.141059 0.257256 0.405081 0.046 Uiso 1 1 calc R . . . .
C10 C 0.5887(4) 0.8002(7) 0.9926(10) 0.0495(16) Uani 1 1 d . . . . .
H10 H 0.592831 0.851226 1.074354 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2151(4) 0.1186(6) 0.6731(9) 0.0463(15) Uani 1 1 d . . . . .
H11 H 0.216745 0.043130 0.714463 0.056 Uiso 1 1 calc R . . . .
C12 C 0.6400(3) 0.7411(6) 0.7703(8) 0.0378(13) Uani 1 1 d . . . . .
N7 N 0.0488(16) 0.345(2) 0.005(3) 0.063(4) Uani 0.206(10) 1 d D U P A 1
O3 O 0.1143(18) 0.412(3) 0.200(3) 0.057(7) Uani 0.206(10) 1 d D U P A 1
C13 C 0.0513(16) 0.413(3) 0.147(3) 0.063(4) Uani 0.206(10) 1 d D U P A 1
H13 H 0.010052 0.451844 0.189199 0.076 Uiso 0.206(10) 1 calc R . P A 1
C14 C 0.109(2) 0.280(5) -0.075(6) 0.085(8) Uani 0.206(10) 1 d D U P A 1
H14A H 0.088322 0.245224 -0.164610 0.128 Uiso 0.206(10) 1 calc R . P A 1
H14B H 0.148808 0.333790 -0.101735 0.128 Uiso 0.206(10) 1 calc R . P A 1
H14C H 0.128599 0.219424 -0.010509 0.128 Uiso 0.206(10) 1 calc R . P A 1
C15 C -0.0258(17) 0.340(4) -0.070(4) 0.072(7) Uani 0.206(10) 1 d D U P A 1
H15A H -0.021778 0.294451 -0.160929 0.108 Uiso 0.206(10) 1 calc R . P A 1
H15B H -0.062122 0.304766 -0.003965 0.108 Uiso 0.206(10) 1 calc R . P A 1
H15C H -0.041881 0.419121 -0.095184 0.108 Uiso 0.206(10) 1 calc R . P A 1
C16 C -0.0253(11) 0.425(3) 0.044(4) 0.067(5) Uani 0.294(10) 1 d D U P A 2
H16A H -0.064301 0.398840 -0.023439 0.100 Uiso 0.294(10) 1 calc R . P A 2
H16B H -0.039042 0.405190 0.145901 0.100 Uiso 0.294(10) 1 calc R . P A 2
H16C H -0.019307 0.508911 0.035521 0.100 Uiso 0.294(10) 1 calc R . P A 2
N8 N 0.0466(12) 0.366(2) 0.005(3) 0.060(4) Uani 0.294(10) 1 d D U P A 2
C17 C 0.1110(12) 0.399(3) 0.101(3) 0.068(4) Uani 0.294(10) 1 d D U P A 2
H17 H 0.161175 0.394057 0.069616 0.081 Uiso 0.294(10) 1 calc R . P A 2
C18 C 0.045(2) 0.296(3) -0.134(3) 0.083(6) Uani 0.294(10) 1 d D U P A 2
H18A H -0.005832 0.290263 -0.170567 0.124 Uiso 0.294(10) 1 calc R . P A 2
H18B H 0.076132 0.333793 -0.209349 0.124 Uiso 0.294(10) 1 calc R . P A 2
H18C H 0.064580 0.218367 -0.114393 0.124 Uiso 0.294(10) 1 calc R . P A 2
O4 O 0.0916(15) 0.432(3) 0.224(3) 0.064(6) Uani 0.294(10) 1 d D U 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 1.937(4) . ?
Zn1 N1 2.017(5) 2_665 ?
Zn1 N2 2.011(5) 4 ?
Zn1 N3 1.975(5) . ?
O1 C2 1.282(8) . ?
N1 C3 1.336(10) . ?
N1 C5 1.370(8) . ?
O2 C2 1.230(9) . ?
N2 C9 1.317(8) . ?
N2 C11 1.343(8) . ?
N3 C1 1.367(8) . ?
N3 C3 1.335(11) . ?
N4 C1 1.355(8) . ?
N4 C10 1.336(9) . ?
N5 C10 1.323(11) . ?
N5 C12 1.326(10) . ?
C1 C5 1.378(9) . ?
C2 C6 1.502(9) . ?
N6 H6A 0.8612 . ?
N6 H6B 0.8612 . ?
N6 C12 1.369(9) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C6 1.381(9) . ?
C4 C11 1.379(9) . ?
C5 C12 1.413(8) . ?
C6 C8 1.419(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C8 1.361(9) . ?
C8 C9 1.393(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N7 C13 1.471(13) . ?
N7 C14 1.475(13) . ?
N7 C15 1.479(13) . ?
O3 C13 1.207(13) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N8 1.475(12) . ?
N8 C17 1.464(12) . ?
N8 C18 1.470(13) . ?
C17 H17 0.9300 . ?
C17 O4 1.206(13) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N1 105.1(2) . 2_665 ?
O1 Zn1 N2 111.8(2) . 4 ?
O1 Zn1 N3 114.3(2) . . ?
N2 Zn1 N1 104.3(2) 4 2_665 ?
N3 Zn1 N1 108.0(2) . 2_665 ?
N3 Zn1 N2 112.5(2) . 4 ?
C2 O1 Zn1 115.2(4) . . ?
C3 N1 Zn1 117.1(5) . 2_664 ?
C3 N1 C5 103.5(6) . . ?
C5 N1 Zn1 139.0(4) . 2_664 ?
C9 N2 Zn1 121.4(4) . 4_544 ?
C9 N2 C11 119.9(5) . . ?
C11 N2 Zn1 118.7(4) . 4_544 ?
C1 N3 Zn1 130.8(4) . . ?
C3 N3 Zn1 125.0(5) . . ?
C3 N3 C1 104.0(5) . . ?
C10 N4 C1 110.0(6) . . ?
C10 N5 C12 118.0(6) . . ?
N3 C1 C5 108.4(5) . . ?
N4 C1 N3 124.9(6) . . ?
N4 C1 C5 126.6(6) . . ?
O1 C2 C6 114.4(6) . . ?
O2 C2 O1 124.2(6) . . ?
O2 C2 C6 121.4(6) . . ?
H6A N6 H6B 109.3 . . ?
C12 N6 H6A 109.6 . . ?
C12 N6 H6B 109.5 . . ?
N1 C3 H3 122.4 . . ?
N3 C3 N1 115.2(6) . . ?
N3 C3 H3 122.4 . . ?
C6 C4 H4 119.6 . . ?
C11 C4 H4 119.6 . . ?
C11 C4 C6 120.8(6) . . ?
N1 C5 C1 109.0(5) . . ?
N1 C5 C12 135.1(6) . . ?
C1 C5 C12 116.0(6) . . ?
C4 C6 C2 119.7(6) . . ?
C4 C6 C8 118.0(6) . . ?
C8 C6 C2 122.3(6) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C7 C8 C6 123.4(6) . . ?
C7 C8 C9 119.5(6) . . ?
C9 C8 C6 117.1(6) . . ?
N2 C9 C8 123.5(6) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N4 C10 H10 114.9 . . ?
N5 C10 N4 130.2(7) . . ?
N5 C10 H10 114.9 . . ?
N2 C11 C4 120.7(6) . . ?
N2 C11 H11 119.7 . . ?
C4 C11 H11 119.7 . . ?
N5 C12 N6 118.2(6) . . ?
N5 C12 C5 119.2(6) . . ?
N6 C12 C5 122.6(6) . . ?
C13 N7 C14 131(2) . . ?
C13 N7 C15 115.6(18) . . ?
C14 N7 C15 113.9(18) . . ?
N7 C13 H13 124.6 . . ?
O3 C13 N7 111(2) . . ?
O3 C13 H13 124.6 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
N7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 C16 H16A 109.5 . . ?
N8 C16 H16B 109.5 . . ?
N8 C16 H16C 109.5 . . ?
C17 N8 C16 114.8(15) . . ?
C17 N8 C18 129(2) . . ?
C18 N8 C16 115.3(17) . . ?
N8 C17 H17 123.8 . . ?
O4 C17 N8 112(2) . . ?
O4 C17 H17 123.8 . . ?
N8 C18 H18A 109.5 . . ?
N8 C18 H18B 109.5 . . ?
N8 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 O2 0.5(9) . . . . ?
Zn1 O1 C2 C6 178.4(4) . . . . ?
Zn1 N1 C3 N3 174.1(5) 2_664 . . . ?
Zn1 N1 C5 C1 -171.8(5) 2_664 . . . ?
Zn1 N1 C5 C12 9.3(12) 2_664 . . . ?
Zn1 N2 C9 C8 176.5(5) 4_544 . . . ?
Zn1 N2 C11 C4 -176.2(6) 4_544 . . . ?
Zn1 N3 C1 N4 -3.7(10) . . . . ?
Zn1 N3 C1 C5 175.5(4) . . . . ?
Zn1 N3 C3 N1 -175.9(5) . . . . ?
O1 C2 C6 C4 -3.1(9) . . . . ?
O1 C2 C6 C8 176.1(6) . . . . ?
N1 C5 C12 N5 178.6(7) . . . . ?
N1 C5 C12 N6 -1.5(11) . . . . ?
O2 C2 C6 C4 174.8(7) . . . . ?
O2 C2 C6 C8 -5.9(10) . . . . ?
N3 C1 C5 N1 0.1(7) . . . . ?
N3 C1 C5 C12 179.2(5) . . . . ?
N4 C1 C5 N1 179.2(6) . . . . ?
N4 C1 C5 C12 -1.7(9) . . . . ?
C1 N3 C3 N1 -0.2(9) . . . . ?
C1 N4 C10 N5 0.8(11) . . . . ?
C1 C5 C12 N5 -0.3(9) . . . . ?
C1 C5 C12 N6 179.7(6) . . . . ?
C2 C6 C8 C7 2.6(11) . . . . ?
C2 C6 C8 C9 -177.3(6) . . . . ?
C3 N1 C5 C1 -0.2(7) . . . . ?
C3 N1 C5 C12 -179.1(7) . . . . ?
C3 N3 C1 N4 -179.1(7) . . . . ?
C3 N3 C1 C5 0.1(7) . . . . ?
C4 C6 C8 C7 -178.1(8) . . . . ?
C4 C6 C8 C9 2.0(9) . . . . ?
C5 N1 C3 N3 0.2(9) . . . . ?
C6 C4 C11 N2 -0.2(12) . . . . ?
C6 C8 C9 N2 -0.5(10) . . . . ?
C7 C8 C9 N2 179.6(7) . . . . ?
C9 N2 C11 C4 1.7(10) . . . . ?
C10 N4 C1 N3 -179.6(6) . . . . ?
C10 N4 C1 C5 1.5(9) . . . . ?
C10 N5 C12 N6 -177.8(7) . . . . ?
C10 N5 C12 C5 2.1(10) . . . . ?
C11 N2 C9 C8 -1.4(10) . . . . ?
C11 C4 C6 C2 177.6(6) . . . . ?
C11 C4 C6 C8 -1.7(11) . . . . ?
C12 N5 C10 N4 -2.5(13) . . . . ?
C14 N7 C13 O3 0.1(4) . . . . ?
C15 N7 C13 O3 -179.9(5) . . . . ?
C16 N8 C17 O4 25(5) . . . . ?
C18 N8 C17 O4 -163(3) . . . . ?

_olex2_date_sample_data_collection 2021-04-07
_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 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.576
####################################################################### 
# 
# 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_laq-1-20210420
_database_code_depnum_ccdc_archive 'CCDC 2157692'
loop_
_audit_author_name
_audit_author_address
'Xiaopeng Xuan'
;henan normal university
China
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N7 O2 Zn, C4 H9 N O'
_chemical_formula_sum            'C15 H18 N8 O3 Zn'
_chemical_formula_weight         423.74
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn1 C1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.0312(5)
_cell_length_b                   11.2975(5)
_cell_length_c                   8.6680(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1765.74(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2671
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      71.1990
_cell_measurement_theta_min      4.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4578
_diffrn_reflns_point_group_measured_fraction_full 0.698
_diffrn_reflns_point_group_measured_fraction_max 0.676
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.529
_diffrn_reflns_theta_min         4.619
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  53.00   1.00    1.00    --   35.62-115.00 117.00   26
  2  ω    -27.00   6.00   1.00    1.00    --   35.62 -17.00 -61.00   33
  3  ω     80.00 158.00   1.00    1.41    --  107.12  17.00 107.00   78
  4  ω    116.00 143.00   1.00    1.41    --  107.12 117.00 -62.00   27
  5  ω     42.00  81.00   1.00    1.41    --  107.12-115.00 117.00   39
  6  ω   -101.00 -22.00   1.00    1.00    --  -35.62 -57.00  30.00   79
  7  ω     47.00  76.00   1.00    1.00    --   35.62-117.00-149.00   29
  8  ω     60.00 105.00   1.00    1.00    --   35.62 178.00-120.00   45
  9  ω    103.00 129.00   1.00    1.41    --  107.12 111.00 120.00   26
 10  ω    107.00 174.00   1.00    1.41    --  107.12  61.00   0.00   67
 11  ω     39.00 105.00   1.00    1.41    --  107.12 -95.00-150.00   66
 12  ω     57.00 123.00   1.00    1.41    --  107.12 -45.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0218319000
_diffrn_orient_matrix_UB_12      -0.1289020000
_diffrn_orient_matrix_UB_13      -0.0357796000
_diffrn_orient_matrix_UB_21      0.0816421000
_diffrn_orient_matrix_UB_22      0.0382058000
_diffrn_orient_matrix_UB_23      -0.0173565000
_diffrn_orient_matrix_UB_31      0.0126893000
_diffrn_orient_matrix_UB_32      -0.0229035000
_diffrn_orient_matrix_UB_33      0.1731585000
_diffrn_oxdiff_digest_frames     
;
01d2171d27f62fc9914e40beb8e95d0e4f000287742
;
_diffrn_oxdiff_digest_hkl        
;
01fabc9ee0fc97588a3700c9cfb8cd1e91ab27
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.296
_reflns_Friedel_fraction_full    0.352
_reflns_Friedel_fraction_max     0.332
_reflns_number_gt                2271
_reflns_number_total             2338
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.635
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.121
_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)+(0.0617P)²+2.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1132
_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 Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9), C10(H10)
2.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 0.60684(3) 0.47397(5) 1.01321(11) 0.0181(2) Uani 1 1 d . . . . .
O1 O 0.6687(2) 0.5918(4) 0.9133(5) 0.0274(9) Uani 1 1 d . . . . .
O2 O 0.6952(2) 0.4621(3) 0.7265(6) 0.0298(10) Uani 1 1 d . . . . .
N1 N 0.3495(3) 0.1983(5) 0.9293(6) 0.0298(11) Uani 1 1 d . . . . .
N2 N 0.7925(3) 0.5340(4) 0.5022(9) 0.0326(12) Uani 1 1 d . . . . .
H2A H 0.748779 0.511679 0.471704 0.039 Uiso 1 1 d GR . . . .
H2B H 0.820078 0.543053 0.421107 0.039 Uiso 1 1 d GR . . . .
N3 N 0.4637(2) 0.2699(4) 1.0402(6) 0.0279(11) Uani 1 1 d . . . . .
N4 N 0.8312(2) 0.8403(4) 0.5915(6) 0.0213(9) Uani 1 1 d . . . . .
N6 N 0.2974(3) 0.2703(5) 0.7063(7) 0.0325(12) Uani 1 1 d . . . . .
H6A H 0.262410 0.219143 0.715957 0.039 Uiso 1 1 calc R . . . .
H6B H 0.297482 0.318264 0.629249 0.039 Uiso 1 1 calc R . . . .
N7 N 0.4326(2) 0.4445(4) 0.7026(6) 0.0216(9) Uani 1 1 d . . . . .
N9 N 0.5194(2) 0.4285(4) 0.8897(6) 0.0229(10) Uani 1 1 d . . . . .
C1 C 0.4648(3) 0.3460(5) 0.9183(7) 0.0203(11) Uani 1 1 d . . . . .
C2 C 0.4965(4) 0.4841(6) 0.7609(9) 0.0223(13) Uani 1 1 d . . . . .
H2 H 0.523164 0.545452 0.715805 0.027 Uiso 1 1 calc R . . . .
C3 C 0.4123(3) 0.3550(5) 0.8042(7) 0.0209(11) Uani 1 1 d . . . . .
C4 C 0.3516(3) 0.2751(5) 0.8104(8) 0.0271(12) Uani 1 1 d . . . . .
C5 C 0.4037(3) 0.2008(5) 1.0338(9) 0.0300(14) Uani 1 1 d . . . . .
H5 H 0.399028 0.146559 1.113859 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7005(3) 0.5621(5) 0.7867(7) 0.0237(11) Uani 1 1 d . . . . .
C7 C 0.7458(3) 0.6575(4) 0.7125(7) 0.0201(10) Uani 1 1 d . . . . .
C8 C 0.7445(3) 0.7707(6) 0.7766(7) 0.0278(12) Uani 1 1 d . . . . .
H8 H 0.715007 0.786065 0.862332 0.033 Uiso 1 1 calc R . . . .
C9 C 0.7867(3) 0.8598(5) 0.7133(8) 0.0264(12) Uani 1 1 d . . . . .
H9 H 0.784471 0.935256 0.755903 0.032 Uiso 1 1 calc R . . . .
C10 C 0.8321(3) 0.7329(4) 0.5267(8) 0.0224(10) Uani 1 1 d . . . . .
H10 H 0.862590 0.720851 0.441572 0.027 Uiso 1 1 calc R . . . .
C11 C 0.7895(3) 0.6376(5) 0.5802(7) 0.0228(11) Uani 1 1 d . . . . .
O3 O 0.9129(3) 0.5681(6) 0.2609(8) 0.0598(17) Uani 1 1 d . . . . .
N5 N 0.9647(4) 0.6661(7) 0.0635(8) 0.0576(18) Uani 1 1 d . . . . .
C12 C 1.0398(4) 0.5212(7) 0.1924(13) 0.055(2) Uani 1 1 d . . . . .
H12A H 1.040150 0.481963 0.290674 0.083 Uiso 1 1 calc GR . . . .
H12B H 1.080982 0.574926 0.186683 0.083 Uiso 1 1 calc GR . . . .
H12C H 1.043818 0.463493 0.111589 0.083 Uiso 1 1 calc GR . . . .
C13 C 0.9676(5) 0.5898(7) 0.1740(10) 0.053(2) Uani 1 1 d . . . . .
C14 C 0.8946(5) 0.7308(11) 0.045(2) 0.094(5) Uani 1 1 d . . . . .
H14A H 0.881280 0.766815 0.141819 0.142 Uiso 1 1 calc GR . . . .
H14B H 0.856292 0.676791 0.014382 0.142 Uiso 1 1 calc GR . . . .
H14C H 0.900406 0.791001 -0.031769 0.142 Uiso 1 1 calc GR . . . .
C15 C 1.0273(5) 0.6939(8) -0.0382(11) 0.061(2) Uani 1 1 d . . . . .
H15A H 1.057414 0.754124 0.008478 0.091 Uiso 1 1 calc GR . . . .
H15B H 1.008885 0.721879 -0.135578 0.091 Uiso 1 1 calc GR . . . .
H15C H 1.056534 0.623994 -0.054288 0.091 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.940(4) . ?
Zn1 N4 1.997(4) 4_645 ?
Zn1 N7 2.013(5) 2_665 ?
Zn1 N9 1.974(5) . ?
O1 C6 1.283(7) . ?
O2 C6 1.248(7) . ?
N1 C4 1.348(9) . ?
N1 C5 1.332(9) . ?
N2 C11 1.353(7) . ?
N3 C1 1.363(7) . ?
N3 C5 1.335(7) . ?
N4 C9 1.344(8) . ?
N4 C10 1.337(7) . ?
N6 C4 1.331(8) . ?
N7 C2 1.334(8) . ?
N7 C3 1.391(7) . ?
N9 C1 1.378(7) . ?
N9 C2 1.345(9) . ?
C1 C3 1.372(8) . ?
C3 C4 1.420(7) . ?
C6 C7 1.497(7) . ?
C7 C8 1.395(8) . ?
C7 C11 1.410(8) . ?
C8 C9 1.376(8) . ?
C10 C11 1.402(7) . ?
O3 C13 1.265(10) . ?
N5 C13 1.289(11) . ?
N5 C14 1.469(11) . ?
N5 C15 1.466(11) . ?
C12 C13 1.524(11) . ?

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 N4 110.43(17) . 4_645 ?
O1 Zn1 N7 104.68(18) . 2_665 ?
O1 Zn1 N9 113.3(2) . . ?
N4 Zn1 N7 105.5(2) 4_645 2_665 ?
N9 Zn1 N4 115.8(2) . 4_645 ?
N9 Zn1 N7 106.19(19) . 2_665 ?
C6 O1 Zn1 117.3(4) . . ?
C5 N1 C4 119.0(5) . . ?
C5 N3 C1 110.4(5) . . ?
C9 N4 Zn1 118.5(4) . 4_654 ?
C10 N4 Zn1 122.4(4) . 4_654 ?
C10 N4 C9 119.1(5) . . ?
C2 N7 Zn1 117.4(4) . 2_664 ?
C2 N7 C3 103.4(5) . . ?
C3 N7 Zn1 139.1(4) . 2_664 ?
C1 N9 Zn1 130.4(4) . . ?
C2 N9 Zn1 125.0(4) . . ?
C2 N9 C1 104.2(5) . . ?
N3 C1 N9 125.2(5) . . ?
N3 C1 C3 126.5(5) . . ?
C3 C1 N9 108.2(5) . . ?
N7 C2 N9 115.0(6) . . ?
N7 C3 C4 133.6(5) . . ?
C1 C3 N7 109.1(5) . . ?
C1 C3 C4 117.3(5) . . ?
N1 C4 C3 117.4(5) . . ?
N6 C4 N1 118.1(5) . . ?
N6 C4 C3 124.5(6) . . ?
N1 C5 N3 129.4(6) . . ?
O1 C6 C7 115.0(5) . . ?
O2 C6 O1 124.1(5) . . ?
O2 C6 C7 120.9(5) . . ?
C8 C7 C6 118.7(5) . . ?
C8 C7 C11 118.7(5) . . ?
C11 C7 C6 122.7(5) . . ?
C9 C8 C7 120.2(5) . . ?
N4 C9 C8 121.6(5) . . ?
N4 C10 C11 123.5(5) . . ?
N2 C11 C7 124.5(5) . . ?
N2 C11 C10 118.5(5) . . ?
C10 C11 C7 116.9(5) . . ?
C13 N5 C14 116.6(9) . . ?
C13 N5 C15 124.0(8) . . ?
C15 N5 C14 119.4(9) . . ?
O3 C13 N5 122.7(9) . . ?
O3 C13 C12 120.3(8) . . ?
N5 C13 C12 116.9(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2B O3 0.87 2.19 3.040(8) 165.1 . yes
N6 H6A O2 0.86 2.38 3.213(6) 162.7 3_455 yes
N6 H6B O1 0.86 2.22 3.041(7) 160.9 2_664 yes
C2 H2 N3 0.93 2.59 3.449(9) 153.3 2_664 yes
C2 H2 N9 0.93 2.94 3.378(9) 110.1 2_664 yes
C8 H8 O1 0.93 2.39 2.713(7) 100.2 . yes
C9 H9 N2 0.93 2.78 3.490(9) 134.0 4_655 yes
C9 H9 N7 0.93 3.03 3.438(7) 108.1 3_565 yes
C10 H10 O3 0.93 2.50 3.301(8) 144.3 . yes
C12 H12B N1 0.96 2.82 3.493(11) 128.2 4_654 yes
C14 H14A O2 0.96 2.70 3.452(13) 135.2 4_654 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C6 O2 -1.4(7) . . . . ?
Zn1 O1 C6 C7 178.4(4) . . . . ?
Zn1 N4 C9 C8 -177.7(4) 4_654 . . . ?
Zn1 N4 C10 C11 179.6(4) 4_654 . . . ?
Zn1 N7 C2 N9 178.4(4) 2_664 . . . ?
Zn1 N7 C3 C1 -177.2(4) 2_664 . . . ?
Zn1 N7 C3 C4 3.7(10) 2_664 . . . ?
Zn1 N9 C1 N3 -5.0(8) . . . . ?
Zn1 N9 C1 C3 174.5(4) . . . . ?
Zn1 N9 C2 N7 -174.8(4) . . . . ?
O1 C6 C7 C8 -5.7(8) . . . . ?
O1 C6 C7 C11 174.6(5) . . . . ?
O2 C6 C7 C8 174.2(5) . . . . ?
O2 C6 C7 C11 -5.5(9) . . . . ?
N3 C1 C3 N7 178.8(5) . . . . ?
N3 C1 C3 C4 -1.9(9) . . . . ?
N4 C10 C11 N2 177.5(5) . . . . ?
N4 C10 C11 C7 -2.2(8) . . . . ?
N7 C3 C4 N1 -179.7(6) . . . . ?
N7 C3 C4 N6 1.1(10) . . . . ?
N9 C1 C3 N7 -0.7(6) . . . . ?
N9 C1 C3 C4 178.6(5) . . . . ?
C1 N3 C5 N1 0.2(9) . . . . ?
C1 N9 C2 N7 -0.6(7) . . . . ?
C1 C3 C4 N1 1.3(8) . . . . ?
C1 C3 C4 N6 -178.0(6) . . . . ?
C2 N7 C3 C1 0.3(6) . . . . ?
C2 N7 C3 C4 -178.8(6) . . . . ?
C2 N9 C1 N3 -178.7(6) . . . . ?
C2 N9 C1 C3 0.8(6) . . . . ?
C3 N7 C2 N9 0.2(7) . . . . ?
C4 N1 C5 N3 -0.7(10) . . . . ?
C5 N1 C4 N6 179.2(6) . . . . ?
C5 N1 C4 C3 -0.1(8) . . . . ?
C5 N3 C1 N9 -179.4(5) . . . . ?
C5 N3 C1 C3 1.1(8) . . . . ?
C6 C7 C8 C9 178.6(5) . . . . ?
C6 C7 C11 N2 3.4(9) . . . . ?
C6 C7 C11 C10 -176.9(5) . . . . ?
C7 C8 C9 N4 -1.4(9) . . . . ?
C8 C7 C11 N2 -176.3(6) . . . . ?
C8 C7 C11 C10 3.3(8) . . . . ?
C9 N4 C10 C11 -0.8(8) . . . . ?
C10 N4 C9 C8 2.7(8) . . . . ?
C11 C7 C8 C9 -1.7(9) . . . . ?
C14 N5 C13 O3 1.9(13) . . . . ?
C14 N5 C13 C12 179.3(8) . . . . ?
C15 N5 C13 O3 179.5(7) . . . . ?
C15 N5 C13 C12 -3.2(11) . . . . ?

_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.594
