# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_A1_0m
_database_code_depnum_ccdc_archive 'CCDC 2051947'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)-N'-(2,4-dihydroxybenzylidene)isonicotinohydrazide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N3 O3'
_chemical_formula_weight         257.25

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'

_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'

_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.
;

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                   27.633(7)
_cell_length_b                   5.5391(12)
_cell_length_c                   7.6322(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1168.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      2.9488
_cell_measurement_theta_max      33.1943

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            22746
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.949
_diffrn_reflns_theta_max         33.221
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             4006
_reflns_number_gt                3329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.774
_reflns_Friedel_fraction_full    0.893

_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.
;

_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1183 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.85277(4) 0.8519(2) 0.85637(17) 0.0253(2) Uani 1 1 d . . . . .
H1A H 0.8301(8) 0.759(4) 0.847(3) 0.038 Uiso 1 1 d . U . . .
O2 O 1.02022(4) 0.8605(2) 0.74401(19) 0.0285(3) Uani 1 1 d . . . . .
H2A H 1.0421(8) 0.767(5) 0.708(4) 0.043 Uiso 1 1 d . U . . .
O3 O 0.71832(4) 0.5200(2) 0.92932(17) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.80256(5) 0.4722(2) 0.74750(17) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.76166(4) 0.3322(2) 0.71574(18) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.7634(7) 0.224(4) 0.629(3) 0.027 Uiso 1 1 d . U . . .
N3 N 0.59736(4) -0.0588(2) 0.67873(18) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.84190(5) 0.3906(3) 0.6784(2) 0.0206(3) Uani 1 1 d . . . . .
H1 H 0.840849 0.244856 0.612877 0.025 Uiso 1 1 calc R U . . .
C2 C 0.88745(5) 0.5151(2) 0.69804(19) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.89171(5) 0.7392(2) 0.78561(19) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.93674(5) 0.8505(3) 0.8011(2) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.939609 0.999007 0.862581 0.026 Uiso 1 1 calc R U . . .
C5 C 0.97743(5) 0.7446(3) 0.7269(2) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.97383(5) 0.5232(3) 0.6375(2) 0.0220(3) Uani 1 1 d . . . . .
H6 H 1.001629 0.451234 0.586193 0.026 Uiso 1 1 calc R U . . .
C7 C 0.92920(5) 0.4124(3) 0.62575(19) 0.0208(3) Uani 1 1 d . . . . .
H7 H 0.926750 0.261821 0.566792 0.025 Uiso 1 1 calc R U . . .
C8 C 0.72157(5) 0.3678(3) 0.81218(19) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.67929(5) 0.2109(3) 0.76513(17) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.63320(5) 0.2941(3) 0.8054(2) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.628956 0.443928 0.864039 0.025 Uiso 1 1 calc R U . . .
C11 C 0.59356(5) 0.1556(3) 0.7589(2) 0.0230(3) Uani 1 1 d . . . . .
H11 H 0.562156 0.215303 0.785086 0.028 Uiso 1 1 calc R U . . .
C12 C 0.64186(5) -0.1389(3) 0.6406(2) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.644960 -0.290000 0.582796 0.026 Uiso 1 1 calc R U . . .
C13 C 0.68370(5) -0.0119(3) 0.6816(2) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.714664 -0.075422 0.653269 0.025 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
O1 C3 1.3562(17) . ?
O1 H1A 0.81(2) . ?
O2 C5 1.3521(17) . ?
O2 H2A 0.84(3) . ?
O3 C8 1.2318(17) . ?
N1 C1 1.2899(19) . ?
N1 N2 1.3917(17) . ?
N2 C8 1.3447(19) . ?
N2 H2 0.90(2) . ?
N3 C12 1.3391(19) . ?
N3 C11 1.340(2) . ?
C1 C2 1.4430(19) . ?
C1 H1 0.9500 . ?
C2 C7 1.400(2) . ?
C2 C3 1.4151(19) . ?
C3 C4 1.394(2) . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(2) . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.500(2) . ?
C9 C10 1.389(2) . ?
C9 C13 1.394(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 O1 H1A 106.5(16) . . ?
C5 O2 H2A 107.7(16) . . ?
C1 N1 N2 114.70(12) . . ?
C8 N2 N1 119.47(12) . . ?
C8 N2 H2 123.3(12) . . ?
N1 N2 H2 117.2(12) . . ?
C12 N3 C11 117.70(13) . . ?
N1 C1 C2 121.68(13) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C7 C2 C3 118.31(13) . . ?
C7 C2 C1 118.94(13) . . ?
C3 C2 C1 122.75(13) . . ?
O1 C3 C4 118.10(13) . . ?
O1 C3 C2 121.73(12) . . ?
C4 C3 C2 120.17(13) . . ?
C5 C4 C3 120.07(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O2 C5 C4 117.88(13) . . ?
O2 C5 C6 121.53(13) . . ?
C4 C5 C6 120.59(13) . . ?
C7 C6 C5 118.84(14) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 122.00(13) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
O3 C8 N2 123.89(14) . . ?
O3 C8 C9 120.90(13) . . ?
N2 C8 C9 115.19(12) . . ?
C10 C9 C13 118.37(13) . . ?
C10 C9 C8 117.95(12) . . ?
C13 C9 C8 123.67(13) . . ?
C11 C10 C9 119.01(13) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N3 C11 C10 123.13(13) . . ?
N3 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3 C12 C13 123.19(14) . . ?
N3 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C12 C13 C9 118.58(13) . . ?
C12 C13 H13 120.7 . . ?
C9 C13 H13 120.7 . . ?

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
C1 N1 N2 C8 164.98(15) . . . . ?
N2 N1 C1 C2 179.63(13) . . . . ?
N1 C1 C2 C7 177.50(15) . . . . ?
N1 C1 C2 C3 -3.4(2) . . . . ?
C7 C2 C3 O1 178.86(14) . . . . ?
C1 C2 C3 O1 -0.3(2) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 179.74(14) . . . . ?
O1 C3 C4 C5 -178.40(14) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C3 C4 C5 O2 179.39(14) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
O2 C5 C6 C7 179.41(15) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 179.09(14) . . . . ?
N1 N2 C8 O3 0.2(2) . . . . ?
N1 N2 C8 C9 178.90(13) . . . . ?
O3 C8 C9 C10 23.5(2) . . . . ?
N2 C8 C9 C10 -155.25(14) . . . . ?
O3 C8 C9 C13 -157.33(15) . . . . ?
N2 C8 C9 C13 24.0(2) . . . . ?
C13 C9 C10 C11 -1.0(2) . . . . ?
C8 C9 C10 C11 178.22(13) . . . . ?
C12 N3 C11 C10 -0.9(2) . . . . ?
C9 C10 C11 N3 1.1(2) . . . . ?
C11 N3 C12 C13 0.6(2) . . . . ?
N3 C12 C13 C9 -0.5(2) . . . . ?
C10 C9 C13 C12 0.8(2) . . . . ?
C8 C9 C13 C12 -178.45(14) . . . . ?

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
O1 H1A N1 0.81(2) 1.92(3) 2.6532(17) 150(2) . yes
O2 H2A N3 0.84(3) 1.93(3) 2.7542(18) 167(3) 3 yes
N2 H2 O3 0.90(2) 1.96(2) 2.8418(17) 167.0(18) 4_644 yes
C1 H1 O3 0.95 2.49 3.2553(19) 137.9 4_644 yes
C13 H13 O3 0.95 2.57 3.327(2) 136.3 4_644 yes

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO, Ethanol'
