# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_GUPT-2
_database_code_depnum_ccdc_archive 'CCDC 2031407'
loop_
_audit_author_name
_audit_author_address
'shuhua zhang'
;Guangdong University of Petrochemical Technology
China
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-05-03 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O6 Zn'
_chemical_formula_sum            'C21 H18 N2 O6 Zn'
_chemical_formula_weight         459.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Zn1'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1026(4)
_cell_length_b                   16.5399(8)
_cell_length_c                   19.7752(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3958.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4115
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6580
_cell_measurement_theta_min      3.6050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27503
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.494
_diffrn_reflns_theta_min         3.367
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  61.00   1.00   25.00    --   18.63 -99.00 120.00   39
  2  ω    -87.00 -61.00   1.00   25.00    --  -18.94 -57.00 150.00   26
  3  ω    -46.00  34.00   1.00   25.00    --  -18.94  77.00   0.00   80
  4  ω    -56.00  54.00   1.00   25.00    --  -18.94  19.00 150.00  110
  5  ω    -88.00   8.00   1.00   25.00    --  -18.94 -77.00-150.00   96
  6  ω    -34.00  -1.00   1.00   25.00    --  -18.94 -57.00-120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081815000
_diffrn_orient_matrix_UB_12      -0.0421156000
_diffrn_orient_matrix_UB_13      0.0046218000
_diffrn_orient_matrix_UB_21      0.0052685000
_diffrn_orient_matrix_UB_22      -0.0050282000
_diffrn_orient_matrix_UB_23      -0.0354651000
_diffrn_orient_matrix_UB_31      0.0577920000
_diffrn_orient_matrix_UB_32      0.0064219000
_diffrn_orient_matrix_UB_33      0.0025763000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2582
_reflns_number_total             4079
_reflns_odcompleteness_completeness 99.63
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.039
_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)+(0.0754P)²+5.7855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C18-C19
 1.5 with sigma of 0.01
 C15-C14 \\sim C18-C19
 with sigma of 0.02
 C8-C7 \\sim C18-C19
 with sigma of 0.02
 C9-C8 \\sim C18-C19
 with sigma of 0.02
3. Rigid bond restraints
 C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5A, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O6, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5A, Zn1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
O2 \\sim O5A: within 3.8A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(O4) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5.a Riding coordinates:
 O4(H4), O3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C11(H11), C13(H13), C17(H17), C21(H21), C4(H4A), C3(H3A),
 C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.04681(4) 0.10863(4) 0.63537(3) 0.0476(2) Uani 1 1 d . U . . .
N1 N 0.1948(3) 0.0497(3) 0.62204(18) 0.0481(10) Uani 1 1 d . . . . .
O2 O 0.0119(3) 0.1590(3) 0.54883(18) 0.0658(11) Uani 1 1 d . U . . .
C10 C 0.3036(5) -0.0695(4) 0.6174(3) 0.0674(16) Uani 1 1 d . . . . .
H10 H 0.307070 -0.125440 0.622101 0.081 Uiso 1 1 calc R . . . .
O1 O 0.1535(4) 0.2411(3) 0.5641(2) 0.0800(13) Uani 1 1 d . . . . .
C15 C 0.0634(4) 0.2434(3) 0.4582(2) 0.0502(12) Uani 1 1 d D . . . .
C12 C 0.2875(4) 0.0916(4) 0.6107(3) 0.0600(14) Uani 1 1 d . . . . .
H12 H 0.283243 0.147724 0.609292 0.072 Uiso 1 1 calc R . . . .
C11 C 0.2052(4) -0.0300(4) 0.6261(3) 0.0590(14) Uani 1 1 d . . . . .
H11 H 0.142483 -0.060592 0.635212 0.071 Uiso 1 1 calc R . . . .
C14 C 0.0773(5) 0.2133(4) 0.5287(2) 0.0558(13) Uani 1 1 d D . . . .
C13 C 0.3870(4) 0.0562(4) 0.6012(3) 0.0634(15) Uani 1 1 d . . . . .
H13 H 0.448881 0.088474 0.594290 0.076 Uiso 1 1 calc R . . . .
C9 C 0.3985(4) -0.0258(4) 0.6017(3) 0.0595(14) Uani 1 1 d D . . . .
C8 C 0.5081(4) -0.0661(4) 0.5859(3) 0.0725(17) Uani 1 1 d D . . . .
H8A H 0.499243 -0.099928 0.546242 0.087 Uiso 1 1 calc R . . . .
H8B H 0.562018 -0.024645 0.575159 0.087 Uiso 1 1 calc R . . . .
C7 C 0.5511(5) -0.1163(4) 0.6424(3) 0.0760(19) Uani 1 1 d D . . . .
H7A H 0.499111 -0.159464 0.651942 0.091 Uiso 1 1 calc R . . . .
H7B H 0.557473 -0.083194 0.682731 0.091 Uiso 1 1 calc R . . . .
O6 O -0.0666(6) 0.2978(4) 0.2206(3) 0.135(2) Uani 1 1 d . U . . .
O5A O 0.0839(5) 0.3662(5) 0.2303(3) 0.156(3) Uani 1 1 d . U . . .
C20 C -0.0377(6) 0.2387(4) 0.3535(3) 0.0704(17) Uani 1 1 d . . . . .
O4 O -0.1292(5) 0.2107(3) 0.3183(2) 0.119(2) Uani 1 1 d . U . . .
H4 H -0.130399 0.231261 0.280548 0.178 Uiso 1 1 d R . . . .
C18 C 0.0356(6) 0.2913(4) 0.3237(3) 0.0720(17) Uani 1 1 d D U . . .
C17 C 0.1242(5) 0.3190(4) 0.3610(3) 0.0785(19) Uani 1 1 d . U . . .
H17 H 0.175548 0.352982 0.340676 0.094 Uiso 1 1 calc R . . . .
C21 C -0.0234(5) 0.2151(3) 0.4187(3) 0.0601(14) Uani 1 1 d . . . . .
H21 H -0.073404 0.178805 0.437526 0.072 Uiso 1 1 calc R . . . .
O3 O 0.2248(3) 0.3257(3) 0.4641(3) 0.1036(17) Uani 1 1 d . . . . .
H3 H 0.223631 0.307066 0.502504 0.155 Uiso 1 1 d R . . . .
C16 C 0.1388(4) 0.2968(4) 0.4293(3) 0.0638(15) Uani 1 1 d . . . . .
C19 C 0.0193(7) 0.3181(5) 0.2500(4) 0.090(2) Uani 1 1 d D U . . .
C5 C 0.7564(4) -0.0928(4) 0.6271(3) 0.0573(14) Uani 1 1 d . . . . .
C6 C 0.6658(4) -0.1535(4) 0.6255(4) 0.080(2) Uani 1 1 d . . . . .
H6A H 0.681982 -0.196074 0.657753 0.096 Uiso 1 1 calc R . . . .
H6B H 0.662775 -0.177746 0.580872 0.096 Uiso 1 1 calc R . . . .
C4 C 0.7941(4) -0.0534(4) 0.5715(3) 0.0669(16) Uani 1 1 d . . . . .
H4A H 0.763374 -0.065105 0.529513 0.080 Uiso 1 1 calc R . . . .
C3 C 0.8068(5) -0.0737(4) 0.6864(3) 0.0791(19) Uani 1 1 d . . . . .
H3A H 0.785726 -0.099932 0.726020 0.095 Uiso 1 1 calc R . . . .
C2 C 0.8760(4) 0.0032(4) 0.5758(3) 0.0620(15) Uani 1 1 d . . . . .
H2 H 0.897990 0.029471 0.536489 0.074 Uiso 1 1 calc R . . . .
C1 C 0.8890(5) -0.0157(4) 0.6885(3) 0.0738(18) Uani 1 1 d . . . . .
H1 H 0.920078 -0.002769 0.730099 0.089 Uiso 1 1 calc R . . . .
N2 N 0.9259(3) 0.0226(3) 0.63343(19) 0.0514(11) 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 2.056(4) . ?
Zn1 O2 1.950(3) . ?
Zn1 O5A 1.973(6) 8_566 ?
Zn1 N2 2.041(4) 1_455 ?
N1 C12 1.338(6) . ?
N1 C11 1.326(7) . ?
O2 C14 1.261(7) . ?
C10 C11 1.369(7) . ?
C10 C9 1.393(8) . ?
O1 C14 1.246(6) . ?
C15 C14 1.490(6) . ?
C15 C21 1.390(7) . ?
C15 C16 1.394(7) . ?
C12 C13 1.352(7) . ?
C13 C9 1.363(8) . ?
C9 C8 1.517(7) . ?
C8 C7 1.487(8) . ?
C7 C6 1.554(8) . ?
O6 C19 1.236(9) . ?
O5A C19 1.182(9) . ?
C20 O4 1.388(7) . ?
C20 C18 1.376(9) . ?
C20 C21 1.358(7) . ?
C18 C17 1.379(9) . ?
C18 C19 1.536(6) . ?
C17 C16 1.409(8) . ?
O3 C16 1.336(7) . ?
C5 C6 1.488(8) . ?
C5 C4 1.358(8) . ?
C5 C3 1.358(8) . ?
C4 C2 1.366(8) . ?
C3 C1 1.383(8) . ?
C2 N2 1.328(6) . ?
C1 N2 1.337(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 N1 106.19(16) . . ?
O2 Zn1 O5A 142.5(3) . 8_566 ?
O2 Zn1 N2 97.25(17) . 1_455 ?
O5A Zn1 N1 91.4(2) 8_566 . ?
O5A Zn1 N2 109.1(2) 8_566 1_455 ?
N2 Zn1 N1 106.94(18) 1_455 . ?
C12 N1 Zn1 120.4(4) . . ?
C11 N1 Zn1 123.1(3) . . ?
C11 N1 C12 116.5(4) . . ?
C14 O2 Zn1 116.5(3) . . ?
C11 C10 C9 119.8(6) . . ?
C21 C15 C14 119.9(5) . . ?
C21 C15 C16 118.6(5) . . ?
C16 C15 C14 121.4(5) . . ?
N1 C12 C13 123.1(5) . . ?
N1 C11 C10 123.4(5) . . ?
O2 C14 C15 117.5(5) . . ?
O1 C14 O2 123.3(5) . . ?
O1 C14 C15 119.1(5) . . ?
C12 C13 C9 121.4(5) . . ?
C10 C9 C8 122.6(6) . . ?
C13 C9 C10 115.8(5) . . ?
C13 C9 C8 121.7(5) . . ?
C7 C8 C9 113.4(5) . . ?
C8 C7 C6 111.8(5) . . ?
C19 O5A Zn1 107.8(6) . 8_565 ?
C18 C20 O4 120.8(6) . . ?
C21 C20 O4 118.8(6) . . ?
C21 C20 C18 120.4(6) . . ?
C20 C18 C17 118.8(5) . . ?
C20 C18 C19 120.3(7) . . ?
C17 C18 C19 120.8(7) . . ?
C18 C17 C16 121.6(6) . . ?
C20 C21 C15 122.2(6) . . ?
C15 C16 C17 118.4(6) . . ?
O3 C16 C15 121.7(5) . . ?
O3 C16 C17 119.9(6) . . ?
O6 C19 Zn1 79.8(4) . 8_565 ?
O6 C19 C18 118.4(7) . . ?
O5A C19 Zn1 46.4(4) . 8_565 ?
O5A C19 O6 125.6(7) . . ?
O5A C19 C18 115.0(8) . . ?
C18 C19 Zn1 161.4(7) . 8_565 ?
C4 C5 C6 123.6(6) . . ?
C4 C5 C3 116.0(5) . . ?
C3 C5 C6 120.4(6) . . ?
C5 C6 C7 112.7(5) . . ?
C5 C4 C2 121.4(5) . . ?
C5 C3 C1 120.6(5) . . ?
N2 C2 C4 123.3(5) . . ?
N2 C1 C3 123.1(5) . . ?
C2 N2 Zn1 120.7(4) . 1_655 ?
C2 N2 C1 115.6(5) . . ?
C1 N2 Zn1 123.7(4) . 1_655 ?

_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.821
