The War on hTG2: Warhead Optimization in Small Molecule Human Tissue Transglutaminase Inhibitors
Mader, Lavleen; Watt, Sarah K.I.; Iyer, Harish R.; Nguyen, Linh; Kaur, Harpreet; Keillor, Jeffrey W.; RSC Medicinal Chemistry  (2022) –; doi:10.1039/D2MD00378C

data_7245919
_publ_section_title
;
 The War on hTG2: Warhead Optimization in Small Molecule Human Tissue
 Transglutaminase Inhibitors
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D2MD00378C
_journal_year                    2022
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_name_systematic        '(2E)-2-cyano-3-cyclopropyl-2-propenoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-05-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-14 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.778(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.290(4)
_cell_length_b                   12.586(6)
_cell_length_c                   7.891(4)
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.456
_cell_measurement_theta_min      3.094
_cell_volume                     708.8(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5635
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.669
_diffrn_reflns_theta_min         2.854
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8609.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_recrystallization_method
'Crystallized directly from reaction mixture (toluene)'
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.447
_exptl_crystal_size_min          0.268
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1342
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0427
_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/[\s^2^(Fo^2^)+(0.0537P)^2^+0.1996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                873
_reflns_number_total             1342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2md00378c2.cif
_cod_data_source_block           s1150_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        708.7(6)
_cod_database_code               7245919
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H1-O1
 0.86 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_shelx_res_checksum              83210
_olex2_date_sample_submission    2022-05-14
_olex2_exptl_crystal_mounting_method
'Mounted on a 200uM MicroLoop with Parabar 10312 oil'
_olex2_submission_original_sample_id S1150_LM-1-73
_olex2_submission_special_instructions 'No special instructions were received'