# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ISN-D(-)TA-ACN
_database_code_depnum_ccdc_archive 'CCDC 1916549'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Isoniazid-D-tartaric acid salt'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N6 O14'
_chemical_formula_sum            'C20 H26 N6 O14'
_chemical_formula_weight         574.47

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.8533(2)
_cell_length_b                   15.1576(4)
_cell_length_c                   19.7612(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2352.33(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4924
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      29.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick, 2016'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8495
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.098
_diffrn_reflns_theta_max         29.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             4924
_reflns_number_gt                4467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.592
_reflns_Friedel_fraction_max     0.659
_reflns_Friedel_fraction_full    0.849

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0937P)²+3.4382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 1497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4924
_refine_ls_number_parameters     433
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          5.512
_refine_ls_shift/su_mean         0.033

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
C1 C 0.9736(6) 0.2383(3) 0.7436(2) 0.0187(9) Uani 1 1 d . . . . .
C2 C 1.0215(7) 0.3005(3) 0.6952(2) 0.0254(10) Uani 1 1 d . . . . .
H2 H 1.020189 0.285928 0.648460 0.031 Uiso 1 1 calc R U . . .
C3 C 1.0708(7) 0.3835(3) 0.7162(2) 0.0278(11) Uani 1 1 d . . . . .
H3 H 1.104135 0.426461 0.683791 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0302(7) 0.3459(3) 0.8298(2) 0.0273(11) Uani 1 1 d . . . . .
H4 H 1.035746 0.362472 0.876081 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9790(7) 0.2619(3) 0.8118(2) 0.0229(9) Uani 1 1 d . . . . .
H5 H 0.947769 0.220487 0.845720 0.027 Uiso 1 1 calc R U . . .
C6 C 0.9186(6) 0.1452(3) 0.7281(2) 0.0199(9) Uani 1 1 d . . . . .
H6A H 0.626(14) 0.617(10) 0.631(6) 0.18(6) Uiso 1 1 d D . . . .
H6B H 0.646(5) 0.631(2) 0.676(2) -0.001(10) Uiso 1 1 d D . . . .
C7 C 0.5617(7) 0.3911(3) 0.7338(3) 0.0282(11) Uani 1 1 d . . . . .
C8 C 0.5043(9) 0.3706(4) 0.7984(3) 0.0423(15) Uani 1 1 d . . . . .
H8 H 0.501741 0.414681 0.832569 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4523(9) 0.2878(4) 0.8124(3) 0.0399(14) Uani 1 1 d . . . . .
H9 H 0.417612 0.273701 0.857217 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5034(7) 0.2430(3) 0.7005(3) 0.0309(11) Uani 1 1 d . . . . .
H10 H 0.502095 0.198290 0.666820 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5607(7) 0.3259(3) 0.6847(3) 0.0293(11) Uani 1 1 d . . . . .
H11 H 0.599627 0.338532 0.640190 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6061(9) 0.4837(4) 0.7264(3) 0.0427(14) Uani 1 1 d . . . . .
C13 C 0.3000(6) 0.2388(3) 0.5045(2) 0.0203(9) Uani 1 1 d . . . . .
C14 C 0.2442(6) 0.1431(3) 0.5043(2) 0.0189(9) Uani 1 1 d . . . . .
H14 H 0.120(8) 0.145(4) 0.509(3) 0.025(14) Uiso 1 1 d . . . . .
C15 C 0.3203(6) 0.0930(3) 0.5643(2) 0.0159(8) Uani 1 1 d . . . . .
H15 H 0.280(6) 0.117(3) 0.605(2) 0.006(10) Uiso 1 1 d . . . . .
C16 C 0.2539(6) -0.0022(3) 0.5627(2) 0.0174(8) Uani 1 1 d . . . . .
C17 C 0.2513(6) 0.4923(3) 0.5647(2) 0.0188(9) Uani 1 1 d . . . . .
C18 C 0.3077(6) 0.5897(3) 0.5613(2) 0.0160(8) Uani 1 1 d . . . . .
H18 H 0.306(7) 0.614(4) 0.604(3) 0.016(12) Uiso 1 1 d . . . . .
C19 C 0.1939(6) 0.6387(3) 0.5108(2) 0.0161(8) Uani 1 1 d . . . . .
H19 H 0.072(7) 0.642(3) 0.526(3) 0.016(12) Uiso 1 1 d . . . . .
C20 C 0.2581(5) 0.7332(3) 0.5019(2) 0.0168(8) Uani 1 1 d . . . . .
H1A H 1.096(9) 0.463(2) 0.794(3) 0.044(18) Uiso 1 1 d D . . . .
H2A H 0.868(7) 0.176(3) 0.631(2) 0.020(13) Uiso 1 1 d D . . . .
H3A H 0.706(11) 0.051(5) 0.646(4) 0.05(2) Uiso 1 1 d . . . . .
H4A H 0.319(13) 0.355(6) 0.565(5) 0.09(3) Uiso 1 1 d . . . . .
H7A H 0.886(10) 0.029(5) 0.602(4) 0.05(2) Uiso 1 1 d . . . . .
H11A H 0.499(6) 0.568(3) 0.503(2) 0.014(12) Uiso 1 1 d . . . . .
H12A H 0.088(12) 0.584(5) 0.449(4) 0.07(3) Uiso 1 1 d . . . . .
H5B H 0.400(12) 0.106(5) 0.449(4) 0.07(3) Uiso 1 1 d . . . . .
H6C H 0.539(12) 0.088(6) 0.527(4) 0.07(3) Uiso 1 1 d . . . . .
N1 N 1.0715(6) 0.4032(3) 0.7817(2) 0.0248(9) Uani 1 1 d D . . . .
N2 N 0.8698(6) 0.1323(2) 0.66437(19) 0.0221(8) Uani 1 1 d D . . . .
N3 N 0.8144(6) 0.0469(3) 0.6448(2) 0.0228(8) Uani 1 1 d . . . . .
N4 N 0.4482(6) 0.2241(3) 0.7643(2) 0.0337(10) Uani 1 1 d . . . . .
N5 N 0.6832(8) 0.5073(4) 0.6655(3) 0.0522(16) Uani 1 1 d . . . . .
N6 N 0.7228(8) 0.5918(5) 0.6560(3) 0.0559(17) Uani 1 1 d D . . . .
O1 O 0.9174(6) 0.0891(2) 0.77229(17) 0.0356(10) Uani 1 1 d . . . . .
O2 O 0.5779(8) 0.5461(5) 0.7702(2) 0.0777(19) Uani 1 1 d . . . . .
O3 O 0.3606(6) 0.2740(3) 0.45494(18) 0.0357(9) Uani 1 1 d . . . . .
O4 O 0.2749(5) 0.2783(2) 0.56206(17) 0.0285(8) Uani 1 1 d . . . . .
O5 O 0.2853(5) 0.1014(2) 0.44188(16) 0.0252(7) Uani 1 1 d . . . . .
O6 O 0.4993(4) 0.0991(2) 0.56518(17) 0.0215(7) Uani 1 1 d . . . . .
O7 O 0.0967(4) -0.0123(2) 0.56609(17) 0.0237(7) Uani 1 1 d . . . . .
O8 O 0.3602(4) -0.0639(2) 0.55767(19) 0.0251(7) Uani 1 1 d . . . . .
O9 O 0.3676(5) 0.4348(2) 0.5650(2) 0.0362(9) Uani 1 1 d . . . . .
O10 O 0.0970(4) 0.4770(2) 0.56758(18) 0.0276(8) Uani 1 1 d . . . . .
O11 O 0.4821(4) 0.6012(2) 0.54541(17) 0.0220(7) Uani 1 1 d . . . . .
O12 O 0.1936(5) 0.5943(2) 0.44788(16) 0.0205(6) Uani 1 1 d . . . . .
O13 O 0.2975(5) 0.7644(2) 0.44788(16) 0.0252(7) Uani 1 1 d . . . . .
O14 O 0.2597(5) 0.7758(2) 0.55948(17) 0.0254(7) Uani 1 1 d D . . . .
H5A H 0.698(8) 0.466(4) 0.627(3) 0.034(16) Uiso 1 1 d . . . . .
H3B H 0.822(10) 0.001(5) 0.667(4) 0.05(2) Uiso 1 1 d . . . . .
H14A H 0.291(17) 0.837(3) 0.550(6) 0.14(5) Uiso 1 1 d 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
C1 C2 1.394(6) . ?
C1 C5 1.397(5) . ?
C1 C6 1.506(6) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9500 . ?
C3 N1 1.330(6) . ?
C3 H3 0.9500 . ?
C4 N1 1.328(6) . ?
C4 C5 1.381(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 O1 1.218(5) . ?
C6 N2 1.332(6) . ?
C7 C8 1.390(8) . ?
C7 C11 1.385(7) . ?
C7 C12 1.454(8) . ?
C8 C9 1.349(9) . ?
C8 H8 0.9500 . ?
C9 N4 1.354(7) . ?
C9 H9 0.9500 . ?
C10 N4 1.363(7) . ?
C10 C11 1.371(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O2 1.301(8) . ?
C12 N5 1.393(9) . ?
C13 O3 1.213(6) . ?
C13 O4 1.300(6) . ?
C13 C14 1.516(6) . ?
C14 O5 1.424(5) . ?
C14 C15 1.530(6) . ?
C14 H14 0.98(6) . ?
C15 O6 1.408(5) . ?
C15 C16 1.535(6) . ?
C15 H15 0.94(5) . ?
C16 O7 1.246(6) . ?
C16 O8 1.256(5) . ?
C17 O10 1.235(6) . ?
C17 O9 1.262(6) . ?
C17 C18 1.543(5) . ?
C18 O11 1.416(5) . ?
C18 C19 1.532(6) . ?
C18 H18 0.92(5) . ?
C19 O12 1.413(5) . ?
C19 C20 1.529(6) . ?
C19 H19 1.00(6) . ?
C20 O13 1.207(5) . ?
C20 O14 1.309(5) . ?
N1 H1A 0.96(3) . ?
N2 N3 1.420(5) . ?
N2 H2A 0.94(2) . ?
N3 H3A 0.85(9) . ?
N3 H7A 1.05(8) . ?
N3 H3B 0.82(8) . ?
N5 N6 1.332(9) . ?
N5 H5A 1.00(6) . ?
N6 H6A 0.98(3) . ?
N6 H6B 0.93(2) . ?
O4 H4A 1.22(9) . ?
O5 H5B 0.92(9) . ?
O6 H6C 0.83(9) . ?
O9 H4A 1.26(9) . ?
O11 H11A 0.98(5) . ?
O12 H12A 0.84(9) . ?
O14 H14A 0.98(3) . ?

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
C2 C1 C5 118.7(4) . . ?
C2 C1 C6 124.9(4) . . ?
C5 C1 C6 116.4(4) . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C3 C2 119.9(4) . . ?
N1 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N1 C4 C5 119.4(4) . . ?
N1 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C1 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
O1 C6 N2 124.9(4) . . ?
O1 C6 C1 120.7(4) . . ?
N2 C6 C1 114.3(4) . . ?
C8 C7 C11 118.9(5) . . ?
C8 C7 C12 112.7(5) . . ?
C11 C7 C12 128.3(5) . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 N4 121.7(5) . . ?
C8 C9 H9 119.1 . . ?
N4 C9 H9 119.1 . . ?
N4 C10 C11 120.5(5) . . ?
N4 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C7 119.7(5) . . ?
C10 C11 H11 120.2 . . ?
C7 C11 H11 120.2 . . ?
O2 C12 N5 117.5(6) . . ?
O2 C12 C7 126.5(6) . . ?
N5 C12 C7 116.0(5) . . ?
O3 C13 O4 124.3(4) . . ?
O3 C13 C14 122.1(4) . . ?
O4 C13 C14 113.5(4) . . ?
O5 C14 C13 111.2(4) . . ?
O5 C14 C15 111.2(3) . . ?
C13 C14 C15 111.1(4) . . ?
O5 C14 H14 109(3) . . ?
C13 C14 H14 105(3) . . ?
C15 C14 H14 109(3) . . ?
O6 C15 C14 111.5(4) . . ?
O6 C15 C16 113.7(4) . . ?
C14 C15 C16 108.5(3) . . ?
O6 C15 H15 108(3) . . ?
C14 C15 H15 110(3) . . ?
C16 C15 H15 106(3) . . ?
O7 C16 O8 124.8(4) . . ?
O7 C16 C15 116.8(4) . . ?
O8 C16 C15 118.4(4) . . ?
O10 C17 O9 125.5(4) . . ?
O10 C17 C18 117.6(4) . . ?
O9 C17 C18 117.0(4) . . ?
O11 C18 C19 111.1(3) . . ?
O11 C18 C17 113.8(4) . . ?
C19 C18 C17 109.0(3) . . ?
O11 C18 H18 100(3) . . ?
C19 C18 H18 113(3) . . ?
C17 C18 H18 110(3) . . ?
O12 C19 C20 110.2(3) . . ?
O12 C19 C18 110.1(3) . . ?
C20 C19 C18 109.6(3) . . ?
O12 C19 H19 106(3) . . ?
C20 C19 H19 108(3) . . ?
C18 C19 H19 113(3) . . ?
O13 C20 O14 125.0(4) . . ?
O13 C20 C19 123.6(4) . . ?
O14 C20 C19 111.4(3) . . ?
C4 N1 C3 123.2(4) . . ?
C4 N1 H1A 119(4) . . ?
C3 N1 H1A 118(4) . . ?
C6 N2 N3 118.6(4) . . ?
C6 N2 H2A 124(3) . . ?
N3 N2 H2A 117(3) . . ?
N2 N3 H3A 103(5) . . ?
N2 N3 H7A 107(4) . . ?
H3A N3 H7A 126(6) . . ?
N2 N3 H3B 128(5) . . ?
H3A N3 H3B 96(7) . . ?
H7A N3 H3B 99(6) . . ?
C9 N4 C10 119.5(5) . . ?
N6 N5 C12 118.1(5) . . ?
N6 N5 H5A 118(4) . . ?
C12 N5 H5A 124(4) . . ?
N5 N6 H6A 105(10) . . ?
N5 N6 H6B 114(3) . . ?
H6A N6 H6B 58(9) . . ?
C13 O4 H4A 116(5) . . ?
C14 O5 H5B 94(5) . . ?
C15 O6 H6C 111(7) . . ?
C17 O9 H4A 116(5) . . ?
C18 O11 H11A 105(3) . . ?
C19 O12 H12A 94(6) . . ?
C20 O14 H14A 108(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
C5 C1 C2 C3 -0.7(8) . . . . ?
C6 C1 C2 C3 -179.4(5) . . . . ?
C1 C2 C3 N1 -0.2(8) . . . . ?
N1 C4 C5 C1 0.8(8) . . . . ?
C2 C1 C5 C4 0.5(8) . . . . ?
C6 C1 C5 C4 179.3(5) . . . . ?
C2 C1 C6 O1 162.6(5) . . . . ?
C5 C1 C6 O1 -16.2(7) . . . . ?
C2 C1 C6 N2 -18.9(7) . . . . ?
C5 C1 C6 N2 162.3(5) . . . . ?
C11 C7 C8 C9 1.3(9) . . . . ?
C12 C7 C8 C9 177.6(6) . . . . ?
C7 C8 C9 N4 -2.5(10) . . . . ?
N4 C10 C11 C7 -0.3(8) . . . . ?
C8 C7 C11 C10 0.1(8) . . . . ?
C12 C7 C11 C10 -175.5(6) . . . . ?
C8 C7 C12 O2 -8.6(10) . . . . ?
C11 C7 C12 O2 167.2(7) . . . . ?
C8 C7 C12 N5 172.8(6) . . . . ?
C11 C7 C12 N5 -11.4(10) . . . . ?
O3 C13 C14 O5 4.7(6) . . . . ?
O4 C13 C14 O5 -175.9(4) . . . . ?
O3 C13 C14 C15 129.2(5) . . . . ?
O4 C13 C14 C15 -51.4(5) . . . . ?
O5 C14 C15 O6 68.4(5) . . . . ?
C13 C14 C15 O6 -56.1(5) . . . . ?
O5 C14 C15 C16 -57.5(5) . . . . ?
C13 C14 C15 C16 177.9(4) . . . . ?
O6 C15 C16 O7 175.7(4) . . . . ?
C14 C15 C16 O7 -59.7(5) . . . . ?
O6 C15 C16 O8 -4.7(5) . . . . ?
C14 C15 C16 O8 120.0(4) . . . . ?
O10 C17 C18 O11 -168.8(4) . . . . ?
O9 C17 C18 O11 12.0(6) . . . . ?
O10 C17 C18 C19 -44.1(5) . . . . ?
O9 C17 C18 C19 136.6(4) . . . . ?
O11 C18 C19 O12 72.8(4) . . . . ?
C17 C18 C19 O12 -53.4(5) . . . . ?
O11 C18 C19 C20 -48.6(4) . . . . ?
C17 C18 C19 C20 -174.8(3) . . . . ?
O12 C19 C20 O13 1.9(6) . . . . ?
C18 C19 C20 O13 123.3(5) . . . . ?
O12 C19 C20 O14 -179.9(4) . . . . ?
C18 C19 C20 O14 -58.6(5) . . . . ?
C5 C4 N1 C3 -1.8(8) . . . . ?
C2 C3 N1 C4 1.6(8) . . . . ?
O1 C6 N2 N3 -1.1(8) . . . . ?
C1 C6 N2 N3 -179.6(4) . . . . ?
C8 C9 N4 C10 2.3(9) . . . . ?
C11 C10 N4 C9 -0.8(8) . . . . ?
O2 C12 N5 N6 -0.1(10) . . . . ?
C7 C12 N5 N6 178.6(6) . . . . ?

_refine_diff_density_max         1.874
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.084


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Ethanol'
####################################################################### 
# 
# 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_ISN-D(-)TA-ACN_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1916550'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Isoniazid-D-tartaric acid salt'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 N6 O14'
_chemical_formula_sum            'C20 H13 N6 O14'
_chemical_formula_weight         561.36

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8825(5)
_cell_length_b                   15.1865(9)
_cell_length_c                   19.8838(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2380.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             1148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick, 2016'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11003
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.687
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4831
_reflns_number_gt                4522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.995

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1246P)²+3.2919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.082(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4831
_refine_ls_number_parameters     366
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2369
_refine_ls_wR_factor_gt          0.2243
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_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
C1 C 0.9617(9) 0.2709(5) 0.7391(3) 0.0347(14) Uani 1 1 d . . . . .
C2 C 0.9770(13) 0.2052(5) 0.6907(4) 0.051(2) Uani 1 1 d . . . . .
H2 H 0.949618 0.217365 0.646124 0.061 Uiso 1 1 calc R U . . .
C3 C 1.0315(14) 0.1235(5) 0.7079(4) 0.058(2) Uani 1 1 d . . . . .
H3 H 1.040679 0.079962 0.675192 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0594(10) 0.1693(5) 0.8197(4) 0.0422(17) Uani 1 1 d . . . . .
H4 H 1.088488 0.156440 0.864008 0.051 Uiso 1 1 calc R U . . .
C5 C 1.0051(9) 0.2513(4) 0.8043(3) 0.0390(16) Uani 1 1 d . . . . .
H5 H 0.997238 0.294184 0.837529 0.047 Uiso 1 1 calc R U . . .
H5A H 0.601(13) 0.829(5) 0.627(3) 0.06(3) Uiso 1 1 d D . . . .
C6 C 0.9086(12) 0.3625(5) 0.7262(4) 0.0484(18) Uani 1 1 d . . . . .
C7 C 0.5247(8) 0.7620(4) 0.7433(3) 0.0237(12) Uani 1 1 d . . . . .
C8 C 0.4840(10) 0.6975(4) 0.6948(3) 0.0351(15) Uani 1 1 d . . . . .
H8 H 0.492912 0.710219 0.649154 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4313(10) 0.6162(4) 0.7155(3) 0.0397(16) Uani 1 1 d . . . . .
H9 H 0.402443 0.573633 0.683884 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4584(10) 0.6558(4) 0.8288(3) 0.0362(15) Uani 1 1 d . . . . .
H10 H 0.449157 0.640523 0.873929 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5111(9) 0.7395(4) 0.8108(3) 0.0326(15) Uani 1 1 d . . . . .
H11 H 0.537487 0.780633 0.843838 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5814(9) 0.8548(3) 0.7273(3) 0.0283(13) Uani 1 1 d . . . . .
C13 C 0.7138(9) 0.7378(4) 0.4964(3) 0.0290(13) Uani 1 1 d . . . . .
C14 C 0.7681(8) 0.6413(4) 0.4943(3) 0.0262(12) Uani 1 1 d . . . . .
H14 H 0.891711 0.639479 0.489177 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6893(7) 0.5925(4) 0.4343(3) 0.0230(11) Uani 1 1 d . . . . .
H15 H 0.729642 0.621121 0.393140 0.028 Uiso 1 1 calc R U . . .
C16 C 0.7568(7) 0.4981(4) 0.4344(3) 0.0225(11) Uani 1 1 d . . . . .
C17 C 0.7550(8) 0.2338(4) 0.4995(3) 0.0253(12) Uani 1 1 d . . . . .
C18 C 0.8177(7) 0.1392(3) 0.4902(3) 0.0207(11) Uani 1 1 d . . . . .
H18 H 0.933852 0.140639 0.472636 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7052(7) 0.0905(3) 0.4406(3) 0.0231(11) Uani 1 1 d . . . . .
H19 H 0.723306 0.116471 0.396091 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7609(8) -0.0070(4) 0.4373(3) 0.0263(12) Uani 1 1 d . . . . .
N1 N 1.0726(8) 0.1051(4) 0.7725(3) 0.0430(14) Uani 1 1 d . . . . .
N2 N 0.8293(11) 0.3801(6) 0.6640(4) 0.066(2) Uani 1 1 d . . . . .
N3 N 0.7926(11) 0.4667(7) 0.6522(4) 0.082(3) Uani 1 1 d . . . . .
N4 N 0.4209(7) 0.5975(3) 0.7813(3) 0.0324(12) Uani 1 1 d . . . . .
N5 N 0.6345(7) 0.8673(3) 0.6653(2) 0.0281(11) Uani 1 1 d D . . . .
N6 N 0.6947(7) 0.9520(3) 0.6463(3) 0.0305(12) Uani 1 1 d . . . . .
O1 O 0.9269(12) 0.4259(6) 0.7683(3) 0.092(3) Uani 1 1 d . . . . .
O2 O 0.5797(9) 0.9115(3) 0.7713(2) 0.0544(17) Uani 1 1 d . . . . .
O3 O 0.6534(9) 0.7711(4) 0.5460(3) 0.0547(15) Uani 1 1 d . . . . .
O4 O 0.7351(7) 0.7782(3) 0.4403(2) 0.0401(12) Uani 1 1 d . . . . .
O5 O 0.9110(6) 0.4881(3) 0.4309(3) 0.0375(11) Uani 1 1 d . . . . .
O6 O 0.6493(6) 0.4363(3) 0.4396(3) 0.0361(11) Uani 1 1 d . . . . .
O7 O 0.7256(7) 0.5977(3) 0.5560(2) 0.0393(12) Uani 1 1 d . . . . .
O8 O 0.5102(5) 0.5988(3) 0.4352(2) 0.0298(9) Uani 1 1 d . . . . .
O9 O 0.7164(6) 0.2660(3) 0.5532(2) 0.0347(10) Uani 1 1 d . . . . .
O10 O 0.7525(7) 0.2762(3) 0.4415(2) 0.0358(11) Uani 1 1 d . . . . .
O11 O 0.9153(6) -0.0206(3) 0.4302(3) 0.0418(12) Uani 1 1 d . . . . .
O12 O 0.6465(7) -0.0634(3) 0.4391(4) 0.0543(15) Uani 1 1 d . . . . .
O13 O 0.8178(6) 0.0950(3) 0.5534(2) 0.0294(9) Uani 1 1 d . . . . .
O14 O 0.5313(5) 0.1012(3) 0.4574(2) 0.0317(10) 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
C1 C5 1.373(10) . ?
C1 C2 1.392(10) . ?
C1 C6 1.475(11) . ?
C2 C3 1.357(12) . ?
C2 H2 0.9300 . ?
C3 N1 1.353(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(10) . ?
C4 N1 1.358(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O1 1.283(11) . ?
C6 N2 1.411(11) . ?
C7 C11 1.389(7) . ?
C7 C8 1.412(8) . ?
C7 C12 1.512(8) . ?
C8 C9 1.367(9) . ?
C8 H8 0.9300 . ?
C9 N4 1.340(9) . ?
C9 H9 0.9300 . ?
C10 N4 1.328(8) . ?
C10 C11 1.384(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 O2 1.227(7) . ?
C12 N5 1.316(8) . ?
C13 O3 1.206(8) . ?
C13 O4 1.284(8) . ?
C13 C14 1.528(8) . ?
C14 O7 1.434(7) . ?
C14 C15 1.535(8) . ?
C14 H14 0.9800 . ?
C15 O8 1.415(7) . ?
C15 C16 1.530(7) . ?
C15 H15 0.9800 . ?
C16 O5 1.227(8) . ?
C16 O6 1.268(7) . ?
C17 O9 1.212(7) . ?
C17 O10 1.321(7) . ?
C17 C18 1.531(7) . ?
C18 O13 1.424(6) . ?
C18 C19 1.519(8) . ?
C18 H18 0.9800 . ?
C19 O14 1.420(7) . ?
C19 C20 1.546(7) . ?
C19 H19 0.9800 . ?
C20 O11 1.243(8) . ?
C20 O12 1.243(8) . ?
N2 N3 1.367(12) . ?
N5 N6 1.422(7) . ?
N5 H5A 0.99(3) . ?

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
C5 C1 C2 118.4(7) . . ?
C5 C1 C6 116.0(6) . . ?
C2 C1 C6 125.5(7) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
N1 C3 C2 120.2(7) . . ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 N1 121.8(7) . . ?
C5 C4 H4 119.1 . . ?
N1 C4 H4 119.1 . . ?
C4 C5 C1 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
O1 C6 N2 118.6(8) . . ?
O1 C6 C1 124.2(8) . . ?
N2 C6 C1 117.2(7) . . ?
C11 C7 C8 118.2(5) . . ?
C11 C7 C12 117.1(5) . . ?
C8 C7 C12 124.7(5) . . ?
C9 C8 C7 119.3(6) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N4 C9 C8 120.3(6) . . ?
N4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N4 C10 C11 119.6(6) . . ?
N4 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C7 119.9(6) . . ?
C10 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?
O2 C12 N5 124.7(5) . . ?
O2 C12 C7 120.0(5) . . ?
N5 C12 C7 115.2(5) . . ?
O3 C13 O4 124.1(6) . . ?
O3 C13 C14 122.4(6) . . ?
O4 C13 C14 113.4(5) . . ?
O7 C14 C13 110.7(5) . . ?
O7 C14 C15 110.3(5) . . ?
C13 C14 C15 111.8(5) . . ?
O7 C14 H14 108.0 . . ?
C13 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
O8 C15 C16 114.2(5) . . ?
O8 C15 C14 111.2(5) . . ?
C16 C15 C14 108.1(4) . . ?
O8 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C14 C15 H15 107.7 . . ?
O5 C16 O6 125.1(5) . . ?
O5 C16 C15 117.4(5) . . ?
O6 C16 C15 117.4(5) . . ?
O9 C17 O10 124.6(5) . . ?
O9 C17 C18 124.5(5) . . ?
O10 C17 C18 110.9(5) . . ?
O13 C18 C19 110.1(4) . . ?
O13 C18 C17 109.6(4) . . ?
C19 C18 C17 110.3(5) . . ?
O13 C18 H18 108.9 . . ?
C19 C18 H18 108.9 . . ?
C17 C18 H18 108.9 . . ?
O14 C19 C18 110.8(5) . . ?
O14 C19 C20 113.2(5) . . ?
C18 C19 C20 109.2(4) . . ?
O14 C19 H19 107.8 . . ?
C18 C19 H19 107.8 . . ?
C20 C19 H19 107.8 . . ?
O11 C20 O12 126.8(6) . . ?
O11 C20 C19 116.2(5) . . ?
O12 C20 C19 116.9(5) . . ?
C3 N1 C4 119.4(6) . . ?
N3 N2 C6 115.3(7) . . ?
C10 N4 C9 122.7(5) . . ?
C12 N5 N6 119.0(5) . . ?
C12 N5 H5A 123(6) . . ?
N6 N5 H5A 115(5) . . ?

_refine_diff_density_max         1.384
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.325


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Ethanol'
####################################################################### 
# 
# 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_ISN_DL_TA_EtOH
_database_code_depnum_ccdc_archive 'CCDC 1916551'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Isoniazid-DL-tartaric acid salt'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N3 O7'
_chemical_formula_sum            'C10 H13 N3 O7'
_chemical_formula_weight         287.23

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.409(2)
_cell_length_b                   7.1753(14)
_cell_length_c                   14.653(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.098(10)
_cell_angle_gamma                90
_cell_volume                     1200.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      23.59

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick, 2016'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15957
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2930
_reflns_number_gt                1893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0890P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1663
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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
C1 C 0.52831(19) 0.7622(3) 0.47237(16) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.4633(2) 0.7150(4) 0.37444(18) 0.0317(6) Uani 1 1 d . . . . .
H2 H 0.494973 0.727126 0.326778 0.038 Uiso 1 1 calc R U . . .
C3 C 0.3506(2) 0.6497(4) 0.3489(2) 0.0381(7) Uani 1 1 d . . . . .
H3 H 0.307928 0.616854 0.283106 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3613(2) 0.6814(4) 0.5062(2) 0.0368(6) Uani 1 1 d . . . . .
H4 H 0.326105 0.672664 0.551572 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4752(2) 0.7461(4) 0.53932(19) 0.0322(6) Uani 1 1 d . . . . .
H5 H 0.515464 0.778466 0.605546 0.039 Uiso 1 1 calc R U . . .
C6 C 0.65370(19) 0.8274(3) 0.51228(17) 0.0239(5) Uani 1 1 d . . . . .
C7 C 0.98821(19) 0.7601(3) 0.31290(16) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.98826(18) 0.5496(3) 0.31064(16) 0.0212(5) Uani 1 1 d . . . . .
H8 H 0.984087 0.509332 0.245431 0.025 Uiso 1 1 calc R U . . .
C9 C 0.88067(19) 0.4735(3) 0.32527(16) 0.0197(5) Uani 1 1 d . . . . .
H9 H 0.810372 0.514837 0.269284 0.024 Uiso 1 1 calc R U . . .
C10 C 0.88180(17) 0.2629(3) 0.32640(16) 0.0208(5) Uani 1 1 d . . . . .
H1B H 0.846(2) 0.971(4) 0.454(2) 0.037(8) Uiso 1 1 d . . . . .
H1C H 0.873(3) 0.769(6) 0.494(2) 0.072(11) Uiso 1 1 d . . . . .
H1D H 0.680(2) 0.789(4) 0.388(2) 0.044(8) Uiso 1 1 d . . . . .
H2D H 0.849(2) 0.913(4) 0.555(2) 0.040(8) Uiso 1 1 d . . . . .
H3A H 0.893(3) 0.955(6) 0.252(3) 0.075(12) Uiso 1 1 d . . . . .
H4A H 1.153(3) 0.532(5) 0.383(2) 0.069(11) Uiso 1 1 d . . . . .
H5A H 0.893(3) 0.450(6) 0.454(3) 0.069(11) Uiso 1 1 d . . . . .
N1 N 0.70673(16) 0.8366(3) 0.44704(15) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.82855(17) 0.8799(3) 0.48851(17) 0.0261(5) Uani 1 1 d . . . . .
N3 N 0.29959(18) 0.6310(3) 0.41315(17) 0.0365(6) Uani 1 1 d . . . . .
O1 O 0.70510(15) 0.8732(3) 0.59832(12) 0.0386(5) Uani 1 1 d . . . . .
O2 O 1.06895(16) 0.8506(3) 0.36739(16) 0.0482(6) Uani 1 1 d . . . . .
O3 O 0.89096(15) 0.8310(3) 0.24792(13) 0.0355(5) Uani 1 1 d . . . . .
O4 O 1.08904(15) 0.4724(3) 0.38340(13) 0.0333(5) Uani 1 1 d . . . . .
O5 O 0.87621(15) 0.5460(3) 0.41375(13) 0.0293(4) Uani 1 1 d . . . . .
O6 O 0.89098(16) 0.1825(2) 0.40374(12) 0.0355(5) Uani 1 1 d . . . . .
O7 O 0.87324(14) 0.1844(2) 0.24623(11) 0.0252(4) 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
C1 C2 1.384(3) . ?
C1 C5 1.385(3) . ?
C1 C6 1.506(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 N3 1.332(3) . ?
C3 H3 0.9300 . ?
C4 N3 1.325(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O1 1.214(3) . ?
C6 N1 1.358(3) . ?
C7 O2 1.198(3) . ?
C7 O3 1.312(3) . ?
C7 C8 1.511(3) . ?
C8 O4 1.400(3) . ?
C8 C9 1.533(3) . ?
C8 H8 0.9800 . ?
C9 O5 1.418(3) . ?
C9 C10 1.511(3) . ?
C9 H9 0.9800 . ?
C10 O6 1.236(3) . ?
C10 O7 1.269(3) . ?
N1 N2 1.425(3) . ?
N1 H1D 0.86(3) . ?
N2 H1B 0.90(3) . ?
N2 H1C 0.95(4) . ?
N2 H2D 0.93(3) . ?
O3 H3A 0.89(4) . ?
O4 H4A 0.90(4) . ?
O5 H5A 0.88(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
C2 C1 C5 117.9(2) . . ?
C2 C1 C6 124.9(2) . . ?
C5 C1 C6 117.2(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N3 C3 C2 123.7(2) . . ?
N3 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N3 C4 C5 123.5(2) . . ?
N3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C1 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C1 C5 H5 120.5 . . ?
O1 C6 N1 121.0(2) . . ?
O1 C6 C1 122.0(2) . . ?
N1 C6 C1 117.0(2) . . ?
O2 C7 O3 124.3(2) . . ?
O2 C7 C8 123.3(2) . . ?
O3 C7 C8 112.35(19) . . ?
O4 C8 C7 112.74(18) . . ?
O4 C8 C9 108.63(18) . . ?
C7 C8 C9 110.18(18) . . ?
O4 C8 H8 108.4 . . ?
C7 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
O5 C9 C10 111.12(18) . . ?
O5 C9 C8 110.22(17) . . ?
C10 C9 C8 110.65(18) . . ?
O5 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.3 . . ?
O6 C10 O7 125.8(2) . . ?
O6 C10 C9 118.3(2) . . ?
O7 C10 C9 115.90(19) . . ?
C6 N1 N2 115.9(2) . . ?
C6 N1 H1D 125.6(19) . . ?
N2 N1 H1D 115.9(19) . . ?
N1 N2 H1B 111.6(17) . . ?
N1 N2 H1C 110(2) . . ?
H1B N2 H1C 113(3) . . ?
N1 N2 H2D 108.1(17) . . ?
H1B N2 H2D 111(3) . . ?
H1C N2 H2D 102(3) . . ?
C4 N3 C3 117.2(2) . . ?
C7 O3 H3A 110(2) . . ?
C8 O4 H4A 109(2) . . ?
C9 O5 H5A 104(2) . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
