# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ISO1_01
_database_code_depnum_ccdc_archive 'CCDC 2104467'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT906_ISO1_01             
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.523 Check 
RESPONSE: These can be attributed to the weak data.
The most common place for a high value of K is in the lowest-intensity bin in 
the table. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of 
Fo, thus the high value of Fo/Fc. This is most obvious in the weakest
intensities, since the small addition to Fo becomes insignificant in the ratio 
when Fo is large.
;
_vrf_PLAT911_ISO1_01             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: The data is 99.8 % complete to 0.83 Angstrom.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.229(3)
_cell_length_b                   5.7538(16)
_cell_length_c                   10.095(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.277(18)
_cell_angle_gamma                90
_cell_volume                     589.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    298.36
_cell_measurement_theta_max      68.301
_cell_measurement_theta_min      4.357
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.7213.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.1
_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  0.0485
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_min         4.357
_diffrn_ambient_temperature      298.36
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                823
_reflns_number_total             1075
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.071
_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)+(0.0431P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C6(H6)
2.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O7 O 0.59476(13) 0.2471(2) 0.57511(11) 0.0522(4) Uani 1 1 d . . . . .
N7 N 0.57288(15) 0.1442(3) 0.35847(14) 0.0489(5) Uani 1 1 d . . . . .
H7A H 0.513535 0.042538 0.369418 0.059 Uiso 1 1 calc R U . . .
H7B H 0.597316 0.164296 0.280845 0.059 Uiso 1 1 calc R U . . .
N1 N 0.92661(16) 0.7630(3) 0.39700(17) 0.0533(5) Uani 1 1 d . . . . .
C4 C 0.73017(16) 0.4417(3) 0.43591(16) 0.0371(4) Uani 1 1 d . . . . .
C5 C 0.74692(18) 0.6435(3) 0.51104(18) 0.0445(5) Uani 1 1 d . . . . .
H5 H 0.693496 0.674335 0.576945 0.053 Uiso 1 1 calc R U . . .
C7 C 0.62667(17) 0.2697(3) 0.46121(16) 0.0397(5) Uani 1 1 d . . . . .
C3 C 0.81501(17) 0.4026(3) 0.34154(18) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.807256 0.269664 0.288749 0.054 Uiso 1 1 calc R U . . .
C2 C 0.91113(19) 0.5655(4) 0.3278(2) 0.0513(5) Uani 1 1 d . . . . .
H2 H 0.969163 0.535558 0.266004 0.062 Uiso 1 1 calc R U . . .
C6 C 0.8437(2) 0.7971(4) 0.4866(2) 0.0514(5) Uani 1 1 d . . . . .
H6 H 0.851800 0.934109 0.535832 0.062 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
O7 C7 1.2412(19) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.325(2) . ?
N1 C2 1.333(2) . ?
N1 C6 1.330(3) . ?
C4 C5 1.386(2) . ?
C4 C7 1.495(2) . ?
C4 C3 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.378(3) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?

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
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
C6 N1 C2 116.00(16) . . ?
C5 C4 C7 120.17(15) . . ?
C5 C4 C3 117.87(16) . . ?
C3 C4 C7 121.92(17) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.89(16) . . ?
C6 C5 H5 120.6 . . ?
O7 C7 N7 122.42(16) . . ?
O7 C7 C4 120.18(16) . . ?
N7 C7 C4 117.40(14) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 C4 118.41(18) . . ?
C2 C3 H3 120.8 . . ?
N1 C2 C3 124.47(17) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
N1 C6 C5 124.31(18) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?

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
C4 C5 C6 N1 -2.0(3) . . . . ?
C4 C3 C2 N1 -1.8(3) . . . . ?
C5 C4 C7 O7 -30.6(3) . . . . ?
C5 C4 C7 N7 149.94(18) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C7 C4 C5 C6 179.31(18) . . . . ?
C7 C4 C3 C2 -177.49(17) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C3 C4 C7 O7 146.95(18) . . . . ?
C3 C4 C7 N7 -32.5(3) . . . . ?
C2 N1 C6 C5 0.5(3) . . . . ?
C6 N1 C2 C3 1.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Single-crystal was mounted on to diffractometer using a MiTeGen loop and silicon oil. '
_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_ISO1_07
_database_code_depnum_ccdc_archive 'CCDC 2104473'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT088_ISO1_07             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.18 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT250_ISO1_07             
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note  
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.
;
_vrf_PLAT927_ISO1_07             
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0014 Check 
RESPONSE: The structure was collected at 3.99 GPa. Weighting scheme was applied
to the data.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.300(3)
_cell_length_b                   5.6768(6)
_cell_length_c                   9.5955(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.32(2)
_cell_angle_gamma                90
_cell_volume                     486.19(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.63
_cell_measurement_theta_min      4.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0982 before and 0.0541 after correction. The Ratio of minimum to maximum transmission is 0.8104. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.372
_diffrn_reflns_Laue_measured_fraction_max 0.373
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2132
_diffrn_reflns_point_group_measured_fraction_full 0.372
_diffrn_reflns_point_group_measured_fraction_max 0.373
_diffrn_reflns_theta_full        23.255
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.372
_diffrn_measured_fraction_theta_max 0.373
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                192
_reflns_number_total             261
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         261
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      0.957
_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)+(0.0790P)²+0.2685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 0.4220(15) -0.2924(8) -0.1151(6) 0.043(7) Uani 1 1 d . . . . .
N7 N 0.0557(13) 0.3658(8) -0.1526(5) 0.043(7) Uani 1 1 d . . . . .
H7A H -0.008605 0.468072 -0.141853 0.052 Uiso 1 1 calc R U . . .
H7B H 0.076289 0.354681 -0.234323 0.052 Uiso 1 1 calc R U . . .
O7 O 0.0945(11) 0.2387(7) 0.0762(5) 0.038(7) Uani 1 1 d . . . . .
C2 C 0.4138(19) -0.0790(9) -0.1776(7) 0.033(7) Uani 1 1 d . . . . .
H2 H 0.475938 -0.047144 -0.236176 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3176(17) 0.0942(10) -0.1589(8) 0.041(7) Uani 1 1 d . . . . .
H3 H 0.312206 0.237707 -0.206879 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2289(17) 0.0518(8) -0.0676(7) 0.039(6) Uani 1 1 d . . . . .
C5 C 0.245(2) -0.1625(9) 0.0056(8) 0.039(8) Uani 1 1 d . . . . .
H5 H 0.192300 -0.194264 0.072503 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3417(19) -0.3257(10) -0.0234(8) 0.037(7) Uani 1 1 d . . . . .
H6 H 0.351077 -0.469475 0.024825 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1221(18) 0.2269(9) -0.0446(8) 0.041(7) 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
N1 C2 1.344(7) . ?
N1 C6 1.318(13) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.311(11) . ?
O7 C7 1.258(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(13) . ?
C4 C5 1.392(7) . ?
C4 C7 1.464(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(16) . ?
C6 H6 0.9300 . ?

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
C6 N1 C2 117.1(8) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 118.5 . . ?
N1 C2 C3 122.9(9) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.1(9) . . ?
C3 C4 C7 121.8(5) . . ?
C5 C4 C7 120.0(8) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.3(8) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 124.3(6) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
N7 C7 C4 118.6(5) . . ?
O7 C7 N7 121.6(9) . . ?
O7 C7 C4 119.8(8) . . ?

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
N1 C2 C3 C4 2.5(18) . . . . ?
C2 N1 C6 C5 4(2) . . . . ?
C2 C3 C4 C5 2.3(16) . . . . ?
C2 C3 C4 C7 -179.0(10) . . . . ?
C3 C4 C5 C6 -3.9(18) . . . . ?
C3 C4 C7 N7 33.1(18) . . . . ?
C3 C4 C7 O7 -148.0(10) . . . . ?
C4 C5 C6 N1 1(2) . . . . ?
C5 C4 C7 N7 -148.2(11) . . . . ?
C5 C4 C7 O7 30.7(18) . . . . ?
C6 N1 C2 C3 -5.4(17) . . . . ?
C7 C4 C5 C6 177.3(11) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 3.99 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_04
_database_code_depnum_ccdc_archive 'CCDC 2104470'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_04             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.350 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts
available data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_04             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.16 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT340_ISO1_04             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so impacts on the precision of the bonds lengths.
;
_vrf_PLAT913_ISO1_04             
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          9 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to the data collected e.g. Tungsten powder rings,
diamond reflections.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.528(5)
_cell_length_b                   5.6786(15)
_cell_length_c                   9.709(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.08(5)
_cell_angle_gamma                90
_cell_volume                     509.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.768
_cell_measurement_theta_min      4.191
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0761 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.8725. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            999
_diffrn_reflns_point_group_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.350
_diffrn_reflns_theta_full        23.264
_diffrn_reflns_theta_max         23.264
_diffrn_reflns_theta_min         4.191
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.350
_diffrn_measured_fraction_theta_max 0.350
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                233
_reflns_number_total             259
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.081
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         259
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.022
_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)+(0.0721P)²+0.1434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.4268(8) -0.2837(5) -0.1094(8) 0.038(5) Uani 1 1 d . . . . .
N7 N 0.0584(7) 0.3646(6) -0.1504(8) 0.034(4) Uani 1 1 d . . . . .
H7A H -0.002729 0.469521 -0.138854 0.041 Uiso 1 1 calc R U . . .
H7B H 0.079224 0.350057 -0.231400 0.041 Uiso 1 1 calc R U . . .
O7 O 0.0937(6) 0.2405(4) 0.0743(6) 0.041(4) Uani 1 1 d . . . . .
C2 C 0.4135(9) -0.0756(6) -0.1756(10) 0.036(5) Uani 1 1 d . . . . .
H2 H 0.474035 -0.044016 -0.235405 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3164(8) 0.0936(6) -0.1605(9) 0.035(6) Uani 1 1 d . . . . .
H3 H 0.308476 0.233300 -0.211778 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2300(7) 0.0521(5) -0.0671(8) 0.022(5) Uani 1 1 d . . . . .
C5 C 0.2463(9) -0.1583(6) 0.0068(10) 0.024(5) Uani 1 1 d . . . . .
H5 H 0.194832 -0.188370 0.074922 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3398(8) -0.3196(6) -0.0231(9) 0.030(5) Uani 1 1 d . . . . .
H6 H 0.343355 -0.466368 0.020022 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1200(9) 0.2267(6) -0.0447(10) 0.028(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
N1 C2 1.336(7) . ?
N1 C6 1.330(5) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.311(12) . ?
O7 C7 1.243(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 C5 1.383(7) . ?
C4 C7 1.497(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(5) . ?
C6 H6 0.9300 . ?

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
C6 N1 C2 116.0(4) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 118.1 . . ?
N1 C2 C3 123.9(3) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.5(5) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C7 122.1(4) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 C7 119.4(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 125.0(4) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.5 . . ?
N7 C7 C4 118.5(5) . . ?
O7 C7 N7 122.5(4) . . ?
O7 C7 C4 119.0(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
N1 C2 C3 C4 2.6(16) . . . . ?
C2 N1 C6 C5 -3.5(15) . . . . ?
C2 C3 C4 C5 0.2(14) . . . . ?
C2 C3 C4 C7 -179.6(8) . . . . ?
C3 C4 C5 C6 -4.2(13) . . . . ?
C3 C4 C7 N7 30.1(13) . . . . ?
C3 C4 C7 O7 -147.8(7) . . . . ?
C4 C5 C6 N1 6.1(16) . . . . ?
C5 C4 C7 N7 -149.6(8) . . . . ?
C5 C4 C7 O7 32.5(11) . . . . ?
C6 N1 C2 C3 -1.1(14) . . . . ?
C7 C4 C5 C6 175.5(9) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 2.40 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_06
_database_code_depnum_ccdc_archive 'CCDC 2104472'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_06             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.378 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts
available data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_06             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.30 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT250_ISO1_06             
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used RIGU restraints 
to combat and ensure they are chemically reasonable.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.3656(17)
_cell_length_b                   5.6791(3)
_cell_length_c                   9.6213(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.642(11)
_cell_angle_gamma                90
_cell_volume                     492.79(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    508
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.860
_cell_measurement_theta_min      4.209
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0860 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8990. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.378
_diffrn_reflns_Laue_measured_fraction_max 0.378
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2165
_diffrn_reflns_point_group_measured_fraction_full 0.378
_diffrn_reflns_point_group_measured_fraction_max 0.378
_diffrn_reflns_theta_full        23.278
_diffrn_reflns_theta_max         23.278
_diffrn_reflns_theta_min         4.209
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.378
_diffrn_measured_fraction_theta_max 0.378
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                211
_reflns_number_total             271
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         271
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      0.953
_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)+(0.0767P)²+0.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 0.4238(11) -0.2896(6) -0.1128(4) 0.039(5) Uani 1 1 d . . . . .
N7 N 0.0571(10) 0.3666(6) -0.1520(4) 0.040(5) Uani 1 1 d . . . . .
H7A H -0.007203 0.468014 -0.141015 0.047 Uiso 1 1 calc R U . . .
H7B H 0.078549 0.356305 -0.233226 0.047 Uiso 1 1 calc R U . . .
O7 O 0.0925(8) 0.2394(5) 0.0749(3) 0.036(5) Uani 1 1 d . . . . .
C2 C 0.4140(14) -0.0783(7) -0.1769(6) 0.036(6) Uani 1 1 d . . . . .
H2 H 0.475956 -0.046249 -0.235563 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3159(13) 0.0939(8) -0.1597(6) 0.030(5) Uani 1 1 d . . . . .
H3 H 0.309531 0.236092 -0.208949 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2275(13) 0.0519(6) -0.0687(5) 0.030(5) Uani 1 1 d . . . . .
C5 C 0.2443(15) -0.1607(7) 0.0055(6) 0.035(6) Uani 1 1 d . . . . .
H5 H 0.191688 -0.191248 0.072897 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3402(13) -0.3240(8) -0.0230(6) 0.038(6) Uani 1 1 d . . . . .
H6 H 0.347209 -0.468659 0.023688 0.045 Uiso 1 1 calc R U . . .
C7 C 0.1228(13) 0.2264(7) -0.0440(5) 0.037(5) 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
N1 C2 1.341(5) . ?
N1 C6 1.328(10) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.322(8) . ?
O7 C7 1.253(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(10) . ?
C4 C5 1.390(6) . ?
C4 C7 1.458(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(12) . ?
C6 H6 0.9300 . ?

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
C6 N1 C2 116.9(6) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 118.5 . . ?
N1 C2 C3 122.9(7) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 C7 122.1(4) . . ?
C5 C4 C7 119.7(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.3(6) . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 124.4(4) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
N7 C7 C4 118.2(4) . . ?
O7 C7 N7 120.7(7) . . ?
O7 C7 C4 121.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 2.5(14) . . . . ?
C2 N1 C6 C5 1.2(14) . . . . ?
C2 C3 C4 C5 1.8(13) . . . . ?
C2 C3 C4 C7 179.3(7) . . . . ?
C3 C4 C5 C6 -4.4(13) . . . . ?
C3 C4 C7 N7 33.5(13) . . . . ?
C3 C4 C7 O7 -148.5(8) . . . . ?
C4 C5 C6 N1 3.0(15) . . . . ?
C5 C4 C7 N7 -149.1(8) . . . . ?
C5 C4 C7 O7 29.0(13) . . . . ?
C6 N1 C2 C3 -4.0(13) . . . . ?
C7 C4 C5 C6 178.1(8) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 3.46 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_05
_database_code_depnum_ccdc_archive 'CCDC 2104471'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_05             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.373 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available
data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_05             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.29 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT340_ISO1_05             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.007 Ang.  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so impacts on the precision of the bonds lengths.
;
_vrf_PLAT913_ISO1_05             
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          8 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to the data collected e.g. Tungsten powder rings,
diamond reflections.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.4148(10)
_cell_length_b                   5.6817(4)
_cell_length_c                   9.6396(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.208(11)
_cell_angle_gamma                90
_cell_volume                     497.58(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    984
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.279
_cell_measurement_theta_min      4.203
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0703 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.9092. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.373
_diffrn_reflns_Laue_measured_fraction_max 0.373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2101
_diffrn_reflns_point_group_measured_fraction_full 0.373
_diffrn_reflns_point_group_measured_fraction_max 0.373
_diffrn_reflns_theta_full        23.284
_diffrn_reflns_theta_max         23.284
_diffrn_reflns_theta_min         4.203
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.373
_diffrn_measured_fraction_theta_max 0.373
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                249
_reflns_number_total             270
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         270
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.059
_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)+(0.0734P)²+0.0630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.4245(6) -0.2878(4) -0.1125(6) 0.036(4) Uani 1 1 d . . . . .
N7 N 0.0566(6) 0.3649(5) -0.1512(6) 0.032(3) Uani 1 1 d . . . . .
H7A H -0.005177 0.469707 -0.139557 0.038 Uiso 1 1 calc R U . . .
H7B H 0.076881 0.351685 -0.232804 0.038 Uiso 1 1 calc R U . . .
O7 O 0.0934(4) 0.2391(3) 0.0746(4) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.4139(7) -0.0781(6) -0.1756(7) 0.040(4) Uani 1 1 d . . . . .
H2 H 0.475675 -0.046547 -0.234449 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3181(6) 0.0942(5) -0.1595(7) 0.030(4) Uani 1 1 d . . . . .
H3 H 0.311962 0.235803 -0.209124 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2303(6) 0.0518(5) -0.0670(6) 0.027(4) Uani 1 1 d . . . . .
C5 C 0.2458(7) -0.1591(5) 0.0061(7) 0.022(4) Uani 1 1 d . . . . .
H5 H 0.193692 -0.189084 0.073882 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3398(7) -0.3226(5) -0.0236(7) 0.033(4) Uani 1 1 d . . . . .
H6 H 0.344925 -0.468337 0.021329 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1193(7) 0.2266(5) -0.0455(7) 0.025(3) 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
N1 C2 1.329(5) . ?
N1 C6 1.330(4) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.300(8) . ?
O7 C7 1.246(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C4 C5 1.378(5) . ?
C4 C7 1.495(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(5) . ?
C6 H6 0.9300 . ?

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 N1 C6 116.3(3) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 117.9 . . ?
N1 C2 C3 124.2(2) . . ?
C3 C2 H2 117.9 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.1(4) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C7 122.0(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C7 119.4(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 124.5(4) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
N7 C7 C4 118.9(4) . . ?
O7 C7 N7 122.3(3) . . ?
O7 C7 C4 118.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 2.7(12) . . . . ?
C2 N1 C6 C5 -0.3(11) . . . . ?
C2 C3 C4 C5 1.3(10) . . . . ?
C2 C3 C4 C7 -178.2(6) . . . . ?
C3 C4 C5 C6 -4.4(10) . . . . ?
C3 C4 C7 N7 30.3(9) . . . . ?
C3 C4 C7 O7 -147.5(5) . . . . ?
C4 C5 C6 N1 4.1(12) . . . . ?
C5 C4 C7 N7 -149.2(6) . . . . ?
C5 C4 C7 O7 32.9(8) . . . . ?
C6 N1 C2 C3 -3.2(11) . . . . ?
C7 C4 C5 C6 175.1(7) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 3.23 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_10
_database_code_depnum_ccdc_archive 'CCDC 2104476'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_THETM01_ISO1_10             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT029_ISO1_10             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.370 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts
available data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_10             
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.85 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT213_ISO1_10             
;
PROBLEM: Atom C6              has ADP max/min Ratio .....        4.0 prolat
RESPONSE: Structure is at high pressure.
;
_vrf_PLAT250_ISO1_10             
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note  
RESPONSE: The data are limited due to DAC hence the tensor may be elongated 
due to lack of data in a particular direction. We have used restraints 
to combat and ensure they are chemically reasonable.
;
_vrf_PLAT411_ISO1_10             
;
PROBLEM: Short Inter H...H Contact  H3       ..H5       .       2.09 Ang.  
RESPONSE: Structure is at high pressure.
;
_vrf_PLAT905_ISO1_10             
;
PROBLEM: Negative K value in the Analysis of Variance ...     -0.239 Report
RESPONSE: These can be attributed to the weak data. This is DAC data with large
background.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   13.149(8)
_cell_length_b                   3.4103(10)
_cell_length_c                   10.173(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.11(4)
_cell_angle_gamma                90
_cell_volume                     455.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    170
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.91
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0927 before and 0.0387 after correction. The Ratio of minimum to maximum transmission is 0.8068. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.370
_diffrn_reflns_Laue_measured_fraction_max 0.370
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            945
_diffrn_reflns_point_group_measured_fraction_full 0.370
_diffrn_reflns_point_group_measured_fraction_max 0.370
_diffrn_reflns_theta_full        22.940
_diffrn_reflns_theta_max         22.940
_diffrn_reflns_theta_min         4.012
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.370
_diffrn_measured_fraction_theta_max 0.370
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                155
_reflns_number_total             234
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         234
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      0.909
_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)+(0.0741P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C3-C2
 1.302 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C2(H2)
6.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O7 O 0.5990(10) 0.3294(16) 0.5631(4) 0.035(7) Uani 1 1 d . U . . .
N7 N 0.5657(13) 0.1342(18) 0.3548(5) 0.035(7) Uani 1 1 d . U . . .
H7A H 0.508550 0.032495 0.374296 0.041 Uiso 1 1 calc R U . . .
H7B H 0.584601 0.122757 0.275269 0.041 Uiso 1 1 calc R U . . .
N1 N 0.9313(14) 0.6084(18) 0.3711(5) 0.034(6) Uani 1 1 d . U . . .
C7 C 0.625(2) 0.309(3) 0.4477(7) 0.027(6) Uani 1 1 d . U . . .
C3 C 0.7749(16) 0.336(3) 0.2975(7) 0.021(6) Uani 1 1 d D U . . .
H3 H 0.737973 0.203259 0.230821 0.025 Uiso 1 1 calc R U . . .
C5 C 0.793(2) 0.641(3) 0.5071(8) 0.029(6) Uani 1 1 d . U . . .
H5 H 0.769484 0.713476 0.588214 0.035 Uiso 1 1 calc R U . . .
C4 C 0.725(2) 0.437(3) 0.4130(7) 0.025(6) Uani 1 1 d . U . . .
C6 C 0.886(2) 0.726(3) 0.4803(8) 0.036(6) Uani 1 1 d . U . . .
H6 H 0.924712 0.877583 0.540746 0.043 Uiso 1 1 calc R U . . .
C2 C 0.8686(17) 0.418(4) 0.2806(8) 0.026(6) Uani 1 1 d D U . . .
H2 H 0.895477 0.342737 0.201782 0.031 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
O7 C7 1.241(9) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.33(2) . ?
N1 C6 1.346(17) . ?
N1 C2 1.37(2) . ?
C7 C4 1.45(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.419(19) . ?
C3 C2 1.28(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.45(3) . ?
C5 C6 1.31(4) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?

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
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
C6 N1 C2 115.0(17) . . ?
O7 C7 N7 121.2(18) . . ?
O7 C7 C4 120.8(17) . . ?
N7 C7 C4 117.7(9) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.2(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.4(11) . . ?
C7 C4 C5 121.3(11) . . ?
C3 C4 C7 126.6(14) . . ?
C3 C4 C5 111(2) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 N1 124.4(16) . . ?
C5 C6 H6 117.8 . . ?
N1 C2 H2 117.9 . . ?
C3 C2 N1 124.2(11) . . ?
C3 C2 H2 117.9 . . ?

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
O7 C7 C4 C3 161.3(11) . . . . ?
O7 C7 C4 C5 -9(2) . . . . ?
N7 C7 C4 C3 -12(2) . . . . ?
N7 C7 C4 C5 178.0(10) . . . . ?
C4 C3 C2 N1 0(2) . . . . ?
C4 C5 C6 N1 -6(3) . . . . ?
C6 N1 C2 C3 -3(2) . . . . ?
C6 C5 C4 C7 173.9(19) . . . . ?
C6 C5 C4 C3 2(2) . . . . ?
C2 N1 C6 C5 6(2) . . . . ?
C2 C3 C4 C7 -170.8(18) . . . . ?
C2 C3 C4 C5 0.0(19) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 4.98 GPa. Integration performed with dynamic masking procedure.'
_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_ISO1_08
_database_code_depnum_ccdc_archive 'CCDC 2104474'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_08             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.378 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts
available data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_08             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.23 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT340_ISO1_08             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0078 Ang.  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so impacts on the precision of the bonds lengths.
;
_vrf_PLAT913_ISO1_08             
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          7 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to the data collected e.g. Tungsten powder rings,
diamond reflections.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.2976(12)
_cell_length_b                   5.6740(4)
_cell_length_c                   9.5819(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.290(13)
_cell_angle_gamma                90
_cell_volume                     485.19(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.877
_cell_measurement_theta_min      4.220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0978 before and 0.0437 after correction. The Ratio of minimum to maximum transmission is 0.8753. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.378
_diffrn_reflns_Laue_measured_fraction_max 0.378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2056
_diffrn_reflns_point_group_measured_fraction_full 0.378
_diffrn_reflns_point_group_measured_fraction_max 0.378
_diffrn_reflns_theta_full        23.286
_diffrn_reflns_theta_max         23.286
_diffrn_reflns_theta_min         4.220
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.378
_diffrn_measured_fraction_theta_max 0.378
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                237
_reflns_number_total             265
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         265
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.000
_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)+(0.0614P)²+0.1892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.4233(6) -0.2925(5) -0.1140(6) 0.036(4) Uani 1 1 d . . . . .
N7 N 0.0540(6) 0.3654(5) -0.1524(6) 0.029(3) Uani 1 1 d . . . . .
H7A H -0.008570 0.470268 -0.141108 0.035 Uiso 1 1 calc R U . . .
H7B H 0.073819 0.352445 -0.234486 0.035 Uiso 1 1 calc R U . . .
O7 O 0.0938(5) 0.2385(4) 0.0754(5) 0.035(3) Uani 1 1 d . . . . .
C2 C 0.4133(8) -0.0812(6) -0.1777(8) 0.034(4) Uani 1 1 d . . . . .
H2 H 0.473739 -0.051473 -0.238260 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3190(7) 0.0945(6) -0.1588(7) 0.029(5) Uani 1 1 d . . . . .
H3 H 0.315293 0.238705 -0.205891 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2297(6) 0.0513(5) -0.0680(7) 0.021(4) Uani 1 1 d . . . . .
C5 C 0.2459(7) -0.1608(5) 0.0063(8) 0.024(4) Uani 1 1 d . . . . .
H5 H 0.195222 -0.189442 0.075634 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3384(7) -0.3265(6) -0.0252(8) 0.028(4) Uani 1 1 d . . . . .
H6 H 0.342306 -0.473520 0.018586 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1186(8) 0.2269(6) -0.0455(8) 0.024(3) 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
N1 C2 1.337(5) . ?
N1 C6 1.326(4) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.297(9) . ?
O7 C7 1.245(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 C5 1.385(6) . ?
C4 C7 1.494(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(5) . ?
C6 H6 0.9300 . ?

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
C6 N1 C2 116.4(3) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 118.1 . . ?
N1 C2 C3 123.9(3) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 122.3(4) . . ?
C5 C4 C7 119.0(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 124.6(4) . . ?
N1 C6 H6 117.7 . . ?
C5 C6 H6 117.7 . . ?
N7 C7 C4 118.4(4) . . ?
O7 C7 N7 122.5(3) . . ?
O7 C7 C4 119.1(6) . . ?

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
N1 C2 C3 C4 0.4(12) . . . . ?
C2 N1 C6 C5 -1.3(12) . . . . ?
C2 C3 C4 C5 3.8(11) . . . . ?
C2 C3 C4 C7 -177.2(7) . . . . ?
C3 C4 C5 C6 -6.6(10) . . . . ?
C3 C4 C7 N7 31.8(10) . . . . ?
C3 C4 C7 O7 -146.7(6) . . . . ?
C4 C5 C6 N1 5.5(13) . . . . ?
C5 C4 C7 N7 -149.3(6) . . . . ?
C5 C4 C7 O7 32.3(9) . . . . ?
C6 N1 C2 C3 -1.8(11) . . . . ?
C7 C4 C5 C6 174.5(7) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 4.00 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_03
_database_code_depnum_ccdc_archive 'CCDC 2104469'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_03             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.375 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available
data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_03             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.43 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT340_ISO1_03             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0078 Ang.  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data and so impacts on the precision of the bonds lengths.
;
_vrf_PLAT913_ISO1_03             
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          9 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that gives additional 
background to the data collected e.g. Tungsten powder rings,
diamond reflections.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.629(2)
_cell_length_b                   5.7123(7)
_cell_length_c                   9.773(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.03(2)
_cell_angle_gamma                90
_cell_volume                     523.70(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    906
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.216
_cell_measurement_theta_min      4.160
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1065 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8927. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.375
_diffrn_reflns_Laue_measured_fraction_max 0.375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2034
_diffrn_reflns_point_group_measured_fraction_full 0.375
_diffrn_reflns_point_group_measured_fraction_max 0.375
_diffrn_reflns_theta_full        23.237
_diffrn_reflns_theta_max         23.237
_diffrn_reflns_theta_min         4.160
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.375
_diffrn_measured_fraction_theta_max 0.375
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                255
_reflns_number_total             285
_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 V8.38A (Bruker, 2017)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         285
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      0.973
_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)+(0.0818P)²+0.1710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Rotating group:
 N7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O7 O 0.4067(5) 0.7420(4) 0.4263(5) 0.038(3) Uani 1 1 d . . . . .
N7 N 0.4384(6) 0.8632(6) 0.6488(6) 0.032(3) Uani 1 1 d . . . . .
H7A H 0.465879 0.992694 0.617836 0.039 Uiso 1 1 d R U . . .
H7B H 0.379096 0.893725 0.700610 0.039 Uiso 1 1 d R U . . .
N1 N 0.0734(6) 0.2209(5) 0.6081(6) 0.038(4) Uani 1 1 d . . . . .
C7 C 0.3797(8) 0.7277(6) 0.5451(8) 0.027(3) Uani 1 1 d . . . . .
C4 C 0.2721(6) 0.5525(5) 0.5689(7) 0.029(4) Uani 1 1 d . . . . .
C3 C 0.1834(7) 0.5939(6) 0.6597(7) 0.033(5) Uani 1 1 d . . . . .
H3 H 0.189134 0.733787 0.709307 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2543(7) 0.3440(6) 0.4934(7) 0.031(4) Uani 1 1 d . . . . .
H5 H 0.306495 0.314170 0.425986 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1583(7) 0.1837(6) 0.5204(8) 0.034(4) Uani 1 1 d . . . . .
H6 H 0.152081 0.040102 0.474584 0.041 Uiso 1 1 calc R U . . .
C2 C 0.0871(8) 0.4257(6) 0.6751(8) 0.037(4) Uani 1 1 d . . . . .
H2 H 0.027622 0.456025 0.735892 0.044 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
O7 C7 1.249(6) . ?
N7 H7A 0.8628 . ?
N7 H7B 0.8628 . ?
N7 C7 1.299(9) . ?
N1 C6 1.328(4) . ?
N1 C2 1.332(6) . ?
C7 C4 1.496(5) . ?
C4 C3 1.384(4) . ?
C4 C5 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.367(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(5) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?

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
H7A N7 H7B 109.1 . . ?
C7 N7 H7A 110.6 . . ?
C7 N7 H7B 110.4 . . ?
C6 N1 C2 116.7(3) . . ?
O7 C7 N7 122.7(4) . . ?
O7 C7 C4 119.0(6) . . ?
N7 C7 C4 118.2(4) . . ?
C3 C4 C7 122.3(4) . . ?
C3 C4 C5 117.8(4) . . ?
C5 C4 C7 119.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 123.9(4) . . ?
N1 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
N1 C2 C3 123.9(3) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?

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
O7 C7 C4 C3 -146.2(6) . . . . ?
O7 C7 C4 C5 30.8(10) . . . . ?
N7 C7 C4 C3 32.0(11) . . . . ?
N7 C7 C4 C5 -151.0(7) . . . . ?
C7 C4 C3 C2 179.6(7) . . . . ?
C7 C4 C5 C6 178.0(7) . . . . ?
C4 C3 C2 N1 0.4(12) . . . . ?
C4 C5 C6 N1 4.7(12) . . . . ?
C3 C4 C5 C6 -5.0(10) . . . . ?
C5 C4 C3 C2 2.6(11) . . . . ?
C6 N1 C2 C3 -0.9(11) . . . . ?
C2 N1 C6 C5 -1.7(12) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 1.90 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_11
_database_code_depnum_ccdc_archive 'CCDC 2104477'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_11             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.366 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts available
data. This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_11             
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.90 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT411_ISO1_11             
;
PROBLEM: Short Inter H...H Contact  H1       ..H5       .       2.04 Ang.  
RESPONSE: Structure is at high pressure.
;
_vrf_PLAT414_ISO1_11             
;
PROBLEM: Short Intra D-H..H-X       H2       ..H2B              1.97 Ang.  
RESPONSE: Structure is at high pressure.
;
_vrf_PLAT906_ISO1_11             
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.474 Check 
RESPONSE: These can be attributed to the weak data.
The most common place for a high value of K is in the lowest-intensity bin in
the table. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values of
Fo, thus the high value of Fo/Fc. This is most obvious in the weakest
intensities, since the small addition to Fo becomes insignificant in the ratio
when Fo is large.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   13.177(9)
_cell_length_b                   3.4083(19)
_cell_length_c                   10.184(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.15(7)
_cell_angle_gamma                90
_cell_volume                     456.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    117
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.19
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0347 after correction.
The Ratio of minimum to maximum transmission is 0.6859.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.366
_diffrn_reflns_Laue_measured_fraction_max 0.366
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            591
_diffrn_reflns_point_group_measured_fraction_full 0.366
_diffrn_reflns_point_group_measured_fraction_max 0.366
_diffrn_reflns_theta_full        23.254
_diffrn_reflns_theta_max         23.254
_diffrn_reflns_theta_min         3.096
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.366
_diffrn_measured_fraction_theta_max 0.366
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                119
_reflns_number_total             238
_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 V8.38A (Bruker, 2017)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         238
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      0.879
_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)+(0.0821P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N1-C1
 1.344 with sigma of 0.02
 N2-C6
 1.32 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C4(H4)
4.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_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
O1 O 0.3991(6) 0.332(2) 0.4340(10) 0.054(6) Uani 1 1 d . . . . .
N1 N 0.0697(7) 0.603(3) 0.6273(15) 0.044(7) Uani 1 1 d D . . . .
C6 C 0.3754(10) 0.299(4) 0.5480(19) 0.051(7) Uani 1 1 d D . . . .
N2 N 0.4336(9) 0.133(3) 0.6477(16) 0.055(7) Uani 1 1 d D . . . .
H2A H 0.492572 0.040336 0.632979 0.066 Uiso 1 1 calc R U . . .
H2B H 0.411324 0.121172 0.725396 0.066 Uiso 1 1 calc R U . . .
C1 C 0.1254(10) 0.413(4) 0.7158(18) 0.056(7) Uani 1 1 d D . . . .
H1 H 0.094400 0.322283 0.789805 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2720(12) 0.440(4) 0.588(2) 0.057(7) Uani 1 1 d . . . . .
C5 C 0.1098(9) 0.719(3) 0.5171(15) 0.040(6) Uani 1 1 d . . . . .
H5 H 0.070384 0.858455 0.454493 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2316(10) 0.334(3) 0.7060(18) 0.059(7) Uani 1 1 d . . . . .
H2 H 0.270917 0.219567 0.774262 0.071 Uiso 1 1 calc R U . . .
C4 C 0.2124(12) 0.632(4) 0.495(2) 0.057(7) Uani 1 1 d . . . . .
H4 H 0.239402 0.705134 0.415712 0.068 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 C6 1.224(16) . ?
N1 C1 1.30(2) . ?
N1 C5 1.327(14) . ?
C6 N2 1.36(2) . ?
C6 C3 1.521(14) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 H1 0.9300 . ?
C1 C2 1.433(16) . ?
C3 C2 1.388(19) . ?
C3 C4 1.37(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.416(16) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?

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
C1 N1 C5 119.9(10) . . ?
O1 C6 N2 125.7(11) . . ?
O1 C6 C3 120.3(16) . . ?
N2 C6 C3 114.0(14) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(12) . . ?
C2 C1 H1 118.0 . . ?
C2 C3 C6 122.8(16) . . ?
C4 C3 C6 117.0(16) . . ?
C4 C3 C2 119.6(11) . . ?
N1 C5 H5 119.9 . . ?
N1 C5 C4 120.1(17) . . ?
C4 C5 H5 119.9 . . ?
C1 C2 H2 122.1 . . ?
C3 C2 C1 115.7(17) . . ?
C3 C2 H2 122.1 . . ?
C3 C4 C5 120.4(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?

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
O1 C6 C3 C2 165.2(16) . . . . ?
O1 C6 C3 C4 -5(3) . . . . ?
N1 C1 C2 C3 -6(3) . . . . ?
N1 C5 C4 C3 -2(3) . . . . ?
C6 C3 C2 C1 -165.9(15) . . . . ?
C6 C3 C4 C5 170.4(11) . . . . ?
N2 C6 C3 C2 -13(3) . . . . ?
N2 C6 C3 C4 176(2) . . . . ?
C1 N1 C5 C4 1(3) . . . . ?
C5 N1 C1 C2 3(3) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C4 C3 C2 C1 5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 5.65 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_09
_database_code_depnum_ccdc_archive 'CCDC 2104475'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_ISO1_09             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.375 Why?  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts
available data.
This is exacerbated by the structure being P21/c.
;
_vrf_PLAT088_ISO1_09             
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.12 Note  
RESPONSE: The sample is housed in a Diamond anvil cell that restricts 
available data.
;
_vrf_PLAT906_ISO1_09             
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.256 Check 
RESPONSE: These can be attributed to the weak data.
The most common place for a high value of K is in the lowest-intensity bin in
the table. Almost all area detector integration programs end up 
slightly underestimating the background, resulting in overestimated values
of Fo, thus the high value of Fo/Fc. This is most obvious in the weakest
intensities, since the small addition to Fo becomes insignificant in the ratio
when Fo is large.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.2314(19)
_cell_length_b                   5.6679(4)
_cell_length_c                   9.5601(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.813(12)
_cell_angle_gamma                90
_cell_volume                     478.83(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    518
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.965
_cell_measurement_theta_min      4.229
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0734 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.9046. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.375
_diffrn_reflns_Laue_measured_fraction_max 0.375
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2103
_diffrn_reflns_point_group_measured_fraction_full 0.375
_diffrn_reflns_point_group_measured_fraction_max 0.375
_diffrn_reflns_theta_full        23.178
_diffrn_reflns_theta_max         23.178
_diffrn_reflns_theta_min         4.229
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.375
_diffrn_measured_fraction_theta_max 0.375
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                205
_reflns_number_total             256
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         256
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0387
_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)+(0.0686P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.4228(11) -0.2948(6) -0.1151(5) 0.034(5) Uani 1 1 d . . . . .
N7 N 0.0543(9) 0.3668(6) -0.1527(4) 0.033(5) Uani 1 1 d . . . . .
H7A H -0.009815 0.469998 -0.141708 0.039 Uiso 1 1 calc R U . . .
H7B H 0.074459 0.355551 -0.234809 0.039 Uiso 1 1 calc R U . . .
O7 O 0.0947(8) 0.2384(5) 0.0767(4) 0.031(5) Uani 1 1 d . . . . .
C2 C 0.4147(14) -0.0815(7) -0.1774(6) 0.028(6) Uani 1 1 d . . . . .
H2 H 0.477165 -0.050146 -0.236028 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3186(13) 0.0934(8) -0.1589(6) 0.028(5) Uani 1 1 d . . . . .
H3 H 0.313911 0.237290 -0.206758 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2292(13) 0.0517(6) -0.0679(5) 0.026(5) Uani 1 1 d . . . . .
C5 C 0.2433(15) -0.1633(6) 0.0049(6) 0.030(6) Uani 1 1 d . . . . .
H5 H 0.189478 -0.194358 0.071390 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3394(13) -0.3282(7) -0.0245(6) 0.032(6) Uani 1 1 d . . . . .
H6 H 0.346630 -0.473435 0.022263 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1216(13) 0.2263(6) -0.0439(6) 0.030(5) 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
N1 C2 1.341(5) . ?
N1 C6 1.328(10) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C7 1.314(8) . ?
O7 C7 1.250(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(9) . ?
C4 C5 1.391(5) . ?
C4 C7 1.467(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(11) . ?
C6 H6 0.9300 . ?

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
C6 N1 C2 116.7(6) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
N1 C2 H2 118.4 . . ?
N1 C2 C3 123.2(6) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.6(7) . . ?
C3 C4 C7 122.6(4) . . ?
C5 C4 C7 118.9(6) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.8(6) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 124.6(4) . . ?
N1 C6 H6 117.7 . . ?
C5 C6 H6 117.7 . . ?
N7 C7 C4 118.1(4) . . ?
O7 C7 N7 121.5(7) . . ?
O7 C7 C4 120.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 2.3(13) . . . . ?
C2 N1 C6 C5 2.3(14) . . . . ?
C2 C3 C4 C5 1.9(12) . . . . ?
C2 C3 C4 C7 -178.8(7) . . . . ?
C3 C4 C5 C6 -3.8(13) . . . . ?
C3 C4 C7 N7 32.9(13) . . . . ?
C3 C4 C7 O7 -147.5(7) . . . . ?
C4 C5 C6 N1 1.7(15) . . . . ?
C5 C4 C7 N7 -147.9(8) . . . . ?
C5 C4 C7 O7 31.7(13) . . . . ?
C6 N1 C2 C3 -4.3(13) . . . . ?
C7 C4 C5 C6 177.0(8) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 4.33 GPa. Integration performed with dynamic masking procedure. '
_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_ISO1_02
_database_code_depnum_ccdc_archive 'CCDC 2104468'
loop_
_audit_author_name
_audit_author_address
'Iain D.H. Oswald'
;The University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT088_ISO1_02             
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.65 Note  
RESPONSE: The sample is housed in a Diamond Anvil Cell that restricts available
data. This is exacerbated by the structure being P21/c.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        Isonicotinamide
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_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'

_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                   9.599(2)
_cell_length_b                   5.6979(4)
_cell_length_c                   9.7492(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.402(14)
_cell_angle_gamma                90
_cell_volume                     518.68(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    656
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      4.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0877 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9021.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method 
'Produced from slow evaporation of a filtered saturated solution of isonicotinamide Form I in ethanol at room temperature.'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.371
_diffrn_reflns_Laue_measured_fraction_max 0.372
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2303
_diffrn_reflns_point_group_measured_fraction_full 0.371
_diffrn_reflns_point_group_measured_fraction_max 0.372
_diffrn_reflns_theta_full        23.272
_diffrn_reflns_theta_max         23.272
_diffrn_reflns_theta_min         4.172
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.371
_diffrn_measured_fraction_theta_max 0.372
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                233
_reflns_number_total             281
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         281
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.023
_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)+(0.0551P)²+0.0783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0853
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N7-H7B
 0.93 with sigma of 0.02
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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
N1 N 0.4258(9) -0.2819(5) -0.1094(3) 0.038(5) Uani 1 1 d . . . . .
N7 N 0.0590(8) 0.3657(6) -0.1502(3) 0.038(5) Uani 1 1 d D . . . .
H7A H 0.100(10) 0.349(6) -0.229(5) 0.041(11) Uiso 1 1 d . . . . .
H7B H 0.017(8) 0.504(6) -0.126(5) 0.059(14) Uiso 1 1 d D . . . .
O7 O 0.0929(7) 0.2417(4) 0.0737(3) 0.040(5) Uani 1 1 d . . . . .
C2 C 0.4128(11) -0.0738(7) -0.1752(4) 0.033(5) Uani 1 1 d . . . . .
H2 H 0.478(10) -0.046(5) -0.237(4) 0.035(11) Uiso 1 1 d . . . . .
C3 C 0.3168(11) 0.0951(8) -0.1599(4) 0.032(5) Uani 1 1 d . . . . .
H3 H 0.322(11) 0.241(7) -0.208(4) 0.048(11) Uiso 1 1 d . . . . .
C4 C 0.2276(10) 0.0530(6) -0.0679(4) 0.029(4) Uani 1 1 d . . . . .
C5 C 0.2443(13) -0.1575(6) 0.0051(5) 0.033(5) Uani 1 1 d . . . . .
H5 H 0.191(10) -0.183(6) 0.076(4) 0.038(12) Uiso 1 1 d . . . . .
C6 C 0.3418(12) -0.3171(7) -0.0204(4) 0.035(5) Uani 1 1 d . . . . .
H6 H 0.359(10) -0.469(6) 0.032(4) 0.044(11) Uiso 1 1 d . . . . .
C7 C 0.1230(11) 0.2272(6) -0.0440(4) 0.030(5) 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
N1 C2 1.340(5) . ?
N1 C6 1.330(9) . ?
N7 H7A 0.94(5) . ?
N7 H7B 0.94(2) . ?
N7 C7 1.333(7) . ?
O7 C7 1.249(4) . ?
C2 H2 0.97(6) . ?
C2 C3 1.364(10) . ?
C3 H3 0.97(4) . ?
C3 C4 1.397(9) . ?
C4 C5 1.385(5) . ?
C4 C7 1.468(10) . ?
C5 H5 0.96(6) . ?
C5 C6 1.369(11) . ?
C6 H6 1.00(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
C6 N1 C2 116.3(6) . . ?
H7A N7 H7B 125(3) . . ?
C7 N7 H7A 112(4) . . ?
C7 N7 H7B 117(3) . . ?
N1 C2 H2 116(3) . . ?
N1 C2 C3 124.2(6) . . ?
C3 C2 H2 120(3) . . ?
C2 C3 H3 116(5) . . ?
C2 C3 C4 118.6(4) . . ?
C4 C3 H3 125(5) . . ?
C3 C4 C7 122.0(4) . . ?
C5 C4 C3 117.6(6) . . ?
C5 C4 C7 120.4(6) . . ?
C4 C5 H5 119(3) . . ?
C6 C5 C4 119.0(6) . . ?
C6 C5 H5 122(3) . . ?
N1 C6 C5 124.2(4) . . ?
N1 C6 H6 114(4) . . ?
C5 C6 H6 122(4) . . ?
N7 C7 C4 119.1(3) . . ?
O7 C7 N7 120.7(6) . . ?
O7 C7 C4 120.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 1.4(12) . . . . ?
C2 N1 C6 C5 0.9(11) . . . . ?
C2 C3 C4 C5 1.4(11) . . . . ?
C2 C3 C4 C7 179.1(6) . . . . ?
C3 C4 C5 C6 -2.9(11) . . . . ?
C3 C4 C7 N7 33.8(11) . . . . ?
C3 C4 C7 O7 -147.5(7) . . . . ?
C4 C5 C6 N1 1.8(13) . . . . ?
C5 C4 C7 N7 -148.6(7) . . . . ?
C5 C4 C7 O7 30.1(11) . . . . ?
C6 N1 C2 C3 -2.5(11) . . . . ?
C7 C4 C5 C6 179.4(7) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Data were collected on a crystal in a Diamond Anvil Cell at 1.58 GPa. Integration performed with dynamic masking procedure. '
_olex2_submission_special_instructions 'No special instructions were received'
