# 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_1_sq_sq
_database_code_depnum_ccdc_archive 'CCDC 2072696'
loop_
_audit_author_name
_audit_author_address
'Yu Liang'
;JiangSu University of Science and Technogly
China
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C144 H128 N24 O32 Zn12)'
_chemical_formula_sum            'C36 H32 N6 O8 Zn3'
_chemical_formula_weight         872.78
_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      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'

_cell_length_a                   21.169(6)
_cell_length_b                   21.169(6)
_cell_length_c                   9.021(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4043(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8795
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.820
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       columnar
_exptl_crystal_F_000             1776
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.360
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3292
_reflns_number_total             3566
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.671
_refine_diff_density_min         -1.472
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.173
_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)+(0.0557P)²+34.7652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C2, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.001
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.04231(3) 0.45438(3) 0.14881(7) 0.0223(2) Uani 1 1 d . . . . .
Zn2 Zn 0.000000 0.500000 0.500000 0.0211(2) Uani 1 2 d S T P . .
C1 C -0.0068(3) 0.2503(3) 0.3259(7) 0.0295(13) Uani 1 1 d . U . . .
H1 H 0.011212 0.253852 0.232184 0.035 Uiso 1 1 calc R . . . .
C2 C -0.0625(5) 0.2388(5) 0.6094(12) 0.0670(15) Uani 1 1 d . U . . .
C3 C -0.0417(3) 0.1864(3) 0.5316(8) 0.0380(15) Uani 1 1 d . U . . .
H3 H -0.045798 0.146608 0.574320 0.046 Uiso 1 1 calc R . . . .
C4 C -0.0541(3) 0.2975(3) 0.5419(7) 0.0355(14) Uani 1 1 d . U . . .
H4 H -0.067563 0.333707 0.591280 0.043 Uiso 1 1 calc R . . . .
C5 C -0.0261(3) 0.3036(3) 0.4024(7) 0.0278(12) Uani 1 1 d . U . . .
C6 C -0.0147(3) 0.1914(3) 0.3916(7) 0.0308(13) Uani 1 1 d . U . . .
C7 C -0.0924(5) 0.2324(5) 0.7626(11) 0.0654(18) Uani 1 1 d . U . . .
C8 C -0.0923(6) 0.2920(6) 0.8469(13) 0.0884(18) Uani 1 1 d . U . . .
H8A H -0.050102 0.308606 0.850770 0.133 Uiso 1 1 calc GR . . . .
H8B H -0.107178 0.284336 0.945725 0.133 Uiso 1 1 calc GR . . . .
H8C H -0.119504 0.322001 0.798929 0.133 Uiso 1 1 calc GR . . . .
C9 C -0.1573(5) 0.2034(6) 0.7435(14) 0.0877(17) Uani 1 1 d . U . . .
H9A H -0.185523 0.234145 0.701989 0.131 Uiso 1 1 calc GR . . . .
H9B H -0.173026 0.189906 0.838228 0.131 Uiso 1 1 calc GR . . . .
H9C H -0.154527 0.167653 0.678270 0.131 Uiso 1 1 calc GR . . . .
C10 C -0.0624(6) 0.1819(6) 0.8506(13) 0.0902(18) Uani 1 1 d . U . . .
H10A H -0.054212 0.146139 0.788055 0.135 Uiso 1 1 calc GR . . . .
H10B H -0.090087 0.169636 0.929725 0.135 Uiso 1 1 calc GR . . . .
H10C H -0.023308 0.197109 0.891174 0.135 Uiso 1 1 calc GR . . . .
C11 C 0.0711(3) 0.3989(3) -0.2899(7) 0.0272(12) Uani 1 1 d . U . . .
C12 C 0.0998(3) 0.3570(3) -0.3910(8) 0.0393(16) Uani 1 1 d . U . . .
H12 H 0.098282 0.363960 -0.492685 0.047 Uiso 1 1 calc R . . . .
C13 C 0.1057(4) 0.3352(3) -0.0788(8) 0.0440(17) Uani 1 1 d . U . . .
H13 H 0.107949 0.328002 0.022763 0.053 Uiso 1 1 calc R . . . .
C14 C 0.1319(4) 0.2949(4) -0.1782(9) 0.054(2) Uani 1 1 d . U . . .
H14 H 0.152118 0.258745 -0.143528 0.064 Uiso 1 1 calc R . . . .
C15 C 0.1296(4) 0.3059(4) -0.3327(9) 0.0491(19) Uani 1 1 d . U . . .
H15 H 0.149147 0.277354 -0.396277 0.059 Uiso 1 1 calc R . . . .
C16 C 0.0749(3) 0.3886(3) -0.1374(7) 0.0288(13) Uani 1 1 d . U . . .
C17 C -0.0133(3) 0.3680(3) 0.3447(7) 0.0288(13) Uani 1 1 d . U . . .
C18 C 0.1332(3) 0.4917(3) 0.3157(7) 0.0278(13) Uani 1 1 d . U . . .
N1 N 0.0427(2) 0.4359(2) -0.0710(5) 0.0268(11) Uani 1 1 d . . . . .
N2 N 0.0200(2) 0.4730(2) -0.1777(5) 0.0220(10) Uani 1 1 d . . . . .
N3 N 0.0357(2) 0.4516(2) -0.3107(5) 0.0258(11) Uani 1 1 d . . . . .
O1 O -0.0338(2) 0.41486(18) 0.4131(5) 0.0303(10) Uani 1 1 d . . . . .
O2 O 0.0193(2) 0.3718(2) 0.2254(5) 0.0363(11) Uani 1 1 d . . . . .
O3 O 0.0829(2) 0.4857(2) 0.3866(5) 0.0393(11) Uani 1 1 d . . . . .
O4 O 0.1341(2) 0.4774(3) 0.1802(5) 0.0429(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.021(5) . ?
Zn1 N2 2.043(5) 5_565 ?
Zn1 O2 1.942(4) . ?
Zn1 O3 2.405(5) . ?
Zn1 O4 2.023(5) . ?
Zn2 N3 2.130(5) 1_556 ?
Zn2 N3 2.130(5) 5_565 ?
Zn2 O1 2.092(4) . ?
Zn2 O1 2.092(4) 5_566 ?
Zn2 O3 2.054(4) . ?
Zn2 O3 2.054(4) 5_566 ?
C1 C5 1.384(8) . ?
C1 C6 1.391(9) . ?
C2 C3 1.385(12) . ?
C2 C4 1.396(12) . ?
C2 C7 1.526(14) . ?
C3 C6 1.389(9) . ?
C4 C5 1.397(9) . ?
C5 C17 1.486(8) . ?
C6 C18 1.490(9) 2 ?
C7 C8 1.473(14) . ?
C7 C9 1.516(14) . ?
C7 C10 1.475(14) . ?
C11 C12 1.410(9) . ?
C11 C16 1.395(9) . ?
C11 N3 1.357(8) . ?
C12 C15 1.359(10) . ?
C13 C14 1.358(10) . ?
C13 C16 1.408(9) . ?
C14 C15 1.414(11) . ?
C16 N1 1.351(8) . ?
C17 O1 1.246(7) . ?
C17 O2 1.280(8) . ?
C18 O3 1.249(7) . ?
C18 O4 1.259(8) . ?
N1 N2 1.331(7) . ?
N2 N3 1.324(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 105.85(19) . 5_565 ?
N1 Zn1 O3 158.03(18) . . ?
N1 Zn1 O4 100.40(19) . . ?
N2 Zn1 O3 84.81(17) 5_565 . ?
O2 Zn1 N1 100.14(19) . . ?
O2 Zn1 N2 118.1(2) . 5_565 ?
O2 Zn1 O3 91.16(18) . . ?
O2 Zn1 O4 114.1(2) . . ?
O4 Zn1 N2 114.9(2) . 5_565 ?
O4 Zn1 O3 57.66(16) . . ?
N3 Zn2 N3 180.0 1_556 5_565 ?
O1 Zn2 N3 90.46(18) 5_566 5_565 ?
O1 Zn2 N3 89.54(18) . 5_565 ?
O1 Zn2 N3 90.46(18) . 1_556 ?
O1 Zn2 N3 89.54(18) 5_566 1_556 ?
O1 Zn2 O1 180.0 . 5_566 ?
O3 Zn2 N3 88.6(2) . 5_565 ?
O3 Zn2 N3 91.4(2) 5_566 5_565 ?
O3 Zn2 N3 91.4(2) . 1_556 ?
O3 Zn2 N3 88.6(2) 5_566 1_556 ?
O3 Zn2 O1 91.21(18) . 5_566 ?
O3 Zn2 O1 88.78(18) . . ?
O3 Zn2 O1 88.78(18) 5_566 5_566 ?
O3 Zn2 O1 91.22(18) 5_566 . ?
O3 Zn2 O3 180.0 5_566 . ?
C5 C1 C6 118.8(6) . . ?
C3 C2 C4 116.9(8) . . ?
C3 C2 C7 121.4(8) . . ?
C4 C2 C7 121.7(8) . . ?
C2 C3 C6 122.0(7) . . ?
C2 C4 C5 121.8(7) . . ?
C1 C5 C4 120.1(6) . . ?
C1 C5 C17 121.3(5) . . ?
C4 C5 C17 118.5(5) . . ?
C1 C6 C18 120.3(6) . 2 ?
C3 C6 C1 120.4(6) . . ?
C3 C6 C18 119.2(6) . 2 ?
C8 C7 C2 113.0(9) . . ?
C8 C7 C9 114.0(9) . . ?
C8 C7 C10 110.1(10) . . ?
C9 C7 C2 108.0(9) . . ?
C10 C7 C2 111.9(9) . . ?
C10 C7 C9 99.1(9) . . ?
C16 C11 C12 121.0(6) . . ?
N3 C11 C12 131.7(6) . . ?
N3 C11 C16 107.3(5) . . ?
C15 C12 C11 116.8(6) . . ?
C14 C13 C16 116.5(7) . . ?
C13 C14 C15 122.2(7) . . ?
C12 C15 C14 121.9(7) . . ?
C11 C16 C13 121.5(6) . . ?
N1 C16 C11 107.0(5) . . ?
N1 C16 C13 131.5(6) . . ?
O1 C17 C5 119.6(5) . . ?
O1 C17 O2 123.7(6) . . ?
O2 C17 C5 116.8(5) . . ?
O3 C18 C6 120.1(6) . 4 ?
O3 C18 O4 119.0(6) . . ?
O4 C18 C6 120.9(5) . 4 ?
C16 N1 Zn1 125.4(4) . . ?
N2 N1 Zn1 126.4(4) . . ?
N2 N1 C16 107.4(5) . . ?
N1 N2 Zn1 125.8(4) . 5_565 ?
N3 N2 Zn1 122.3(4) . 5_565 ?
N3 N2 N1 111.3(4) . . ?
C11 N3 Zn2 134.6(4) . 1_554 ?
N2 N3 Zn2 118.2(3) . 1_554 ?
N2 N3 C11 107.1(5) . . ?
C17 O1 Zn2 138.8(4) . . ?
C17 O2 Zn1 119.4(4) . . ?
Zn2 O3 Zn1 100.32(18) . . ?
C18 O3 Zn1 82.9(4) . . ?
C18 O3 Zn2 165.6(5) . . ?
C18 O4 Zn1 100.4(4) . . ?

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2072698'
loop_
_audit_author_name
_audit_author_address
'Yu Liang'
;JiangSu University of Science and Technogly
China
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N6 Zn'
_chemical_formula_sum            'C12 H8 N6 Zn'
_chemical_formula_weight         301.61
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3420(17)
_cell_length_b                   10.0637(16)
_cell_length_c                   12.093(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.291(3)
_cell_angle_gamma                90
_cell_volume                     1188.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1178
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       columnar
_exptl_crystal_F_000             608
_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  0.0748
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9677
_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         27.101
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      296.15
_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_monochromator  graphite
_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                1695
_reflns_number_total             2611
_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       'SAINT V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_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         0.450
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.007
_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)+(0.0210P)²+1.2242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 0.49822(5) 0.06614(4) 0.64018(4) 0.02485(14) Uani 1 1 d . . . . .
C1 C 0.2035(4) 0.0985(4) 0.4736(4) 0.0289(10) Uani 1 1 d . . . . .
C2 C 0.1365(5) 0.1499(4) 0.5478(4) 0.0376(11) Uani 1 1 d . . . . .
H2 H 0.180820 0.158478 0.627995 0.045 Uiso 1 1 calc R . . . .
C3 C 0.0042(5) 0.1863(5) 0.4971(4) 0.0465(12) Uani 1 1 d . . . . .
H3 H -0.042610 0.221436 0.544182 0.056 Uiso 1 1 calc R . . . .
C4 C -0.0657(5) 0.1732(5) 0.3762(5) 0.0572(15) Uani 1 1 d . . . . .
H4 H -0.156528 0.200343 0.345346 0.069 Uiso 1 1 calc R . . . .
C5 C -0.0022(5) 0.1213(5) 0.3041(5) 0.0517(13) Uani 1 1 d . . . . .
H5 H -0.048384 0.111139 0.224296 0.062 Uiso 1 1 calc R . . . .
C6 C 0.1354(4) 0.0838(4) 0.3539(4) 0.0336(10) Uani 1 1 d . . . . .
C7 C 0.3907(4) -0.0337(4) 0.8383(3) 0.0235(9) Uani 1 1 d . . . . .
C8 C 0.3348(4) 0.0762(4) 0.8761(4) 0.0325(10) Uani 1 1 d . . . . .
H8 H 0.337364 0.160736 0.845805 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2759(4) 0.0529(4) 0.9600(4) 0.0377(11) Uani 1 1 d . . . . .
H9 H 0.235745 0.123442 0.986315 0.045 Uiso 1 1 calc R . . . .
C10 C 0.2738(4) -0.0749(4) 1.0084(4) 0.0375(11) Uani 1 1 d . . . . .
H10 H 0.234039 -0.085678 1.066467 0.045 Uiso 1 1 calc R . . . .
C11 C 0.3290(4) -0.1828(4) 0.9718(3) 0.0309(10) Uani 1 1 d . . . . .
H11 H 0.327405 -0.266896 1.003153 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3878(4) -0.1602(4) 0.8848(3) 0.0239(9) Uani 1 1 d . . . . .
N1 N 0.3349(3) 0.0566(3) 0.4943(3) 0.0289(8) Uani 1 1 d . . . . .
N2 N 0.3426(4) 0.0178(3) 0.3903(3) 0.0319(8) Uani 1 1 d . . . . .
N3 N 0.2240(4) 0.0311(4) 0.3035(3) 0.0393(9) Uani 1 1 d . . . . .
N4 N 0.4574(3) -0.0462(3) 0.7582(3) 0.0266(8) Uani 1 1 d . . . . .
N5 N 0.4938(4) -0.1737(3) 0.7546(3) 0.0281(8) Uani 1 1 d . . . . .
N6 N 0.4535(3) -0.2436(3) 0.8308(3) 0.0261(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.001(3) . ?
Zn1 N2 1.990(3) 3_656 ?
Zn1 N4 1.973(3) . ?
Zn1 N6 1.980(3) 2_656 ?
C1 C2 1.401(5) . ?
C1 C6 1.392(6) . ?
C1 N1 1.364(5) . ?
C2 C3 1.352(6) . ?
C3 C4 1.407(6) . ?
C4 C5 1.358(6) . ?
C5 C6 1.401(6) . ?
C6 N3 1.365(5) . ?
C7 C8 1.393(5) . ?
C7 C12 1.395(5) . ?
C7 N4 1.369(4) . ?
C8 C9 1.365(5) . ?
C9 C10 1.417(6) . ?
C10 C11 1.366(5) . ?
C11 C12 1.398(5) . ?
C12 N6 1.373(4) . ?
N1 N2 1.344(4) . ?
N2 N3 1.333(4) . ?
N4 N5 1.342(4) . ?
N5 N6 1.331(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 108.99(13) 3_656 . ?
N4 Zn1 N1 106.86(13) . . ?
N4 Zn1 N2 106.20(13) . 3_656 ?
N4 Zn1 N6 121.84(13) . 2_656 ?
N6 Zn1 N1 107.01(13) 2_656 . ?
N6 Zn1 N2 105.51(13) 2_656 3_656 ?
C6 C1 C2 121.1(4) . . ?
N1 C1 C2 132.0(4) . . ?
N1 C1 C6 106.8(3) . . ?
C3 C2 C1 116.8(4) . . ?
C2 C3 C4 122.7(5) . . ?
C5 C4 C3 120.8(5) . . ?
C4 C5 C6 117.7(5) . . ?
C1 C6 C5 120.8(4) . . ?
N3 C6 C1 108.8(4) . . ?
N3 C6 C5 130.4(4) . . ?
C8 C7 C12 121.7(4) . . ?
N4 C7 C8 131.8(4) . . ?
N4 C7 C12 106.5(3) . . ?
C9 C8 C7 116.3(4) . . ?
C8 C9 C10 122.3(4) . . ?
C11 C10 C9 121.5(4) . . ?
C10 C11 C12 116.6(4) . . ?
C7 C12 C11 121.6(4) . . ?
N6 C12 C7 106.7(3) . . ?
N6 C12 C11 131.7(3) . . ?
C1 N1 Zn1 130.3(3) . . ?
N2 N1 Zn1 123.0(2) . . ?
N2 N1 C1 106.4(3) . . ?
N1 N2 Zn1 127.3(3) . 3_656 ?
N3 N2 Zn1 119.9(3) . 3_656 ?
N3 N2 N1 112.6(3) . . ?
N2 N3 C6 105.4(3) . . ?
C7 N4 Zn1 137.6(3) . . ?
N5 N4 Zn1 113.3(2) . . ?
N5 N4 C7 108.9(3) . . ?
N6 N5 N4 109.1(3) . . ?
C12 N6 Zn1 130.0(2) . 2_646 ?
N5 N6 Zn1 121.0(2) . 2_646 ?
N5 N6 C12 108.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
