A simple and efficient synthesis of a series of N-(thiazol-2-yl)piperidine-2,6-dione compounds and their interesting NLO properties
Shaiwale, Mayuri; Som, Narayan N.; Jha, Prafulla K.; Ballabh, Amar; CrystEngComm 26 (2024) 3069–3076; doi:10.1039/D4CE00217B

data_7248588
_publ_section_title
;
 A simple and efficient synthesis of a series of
 N-(thiazol-2-yl)piperidine-2,6-dione compounds and their interesting NLO
 properties
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3069
_journal_page_last               3076
_journal_paper_doi               10.1039/D4CE00217B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C9 H10 N2 O2 S'
_chemical_formula_sum            'C9 H10 N2 O2 S'
_chemical_formula_weight         210.25
_chemical_name_systematic        1-(4-methylthiazol-2-yl)piperidine-2,6-dione
_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
_audit_creation_date             2021-02-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.828(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4402(13)
_cell_length_b                   9.0667(12)
_cell_length_c                   10.6841(15)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4580
_cell_measurement_theta_min      4.0200
_cell_volume                     982.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  68.00   1.00    1.00    --   19.60 -19.00 -90.00  121
  2  \w     -3.00  34.00   1.00    1.00    --   19.60 -57.00-180.00   37
  3  \w    -19.00  23.00   1.00    1.00    --  -20.54 -99.00 -30.00   42
  4  \w    -99.00 -61.00   1.00    1.00    --  -20.54 178.00  30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0257466000
_diffrn_orient_matrix_UB_12      -0.0299107000
_diffrn_orient_matrix_UB_13      -0.0622896000
_diffrn_orient_matrix_UB_21      -0.0119617000
_diffrn_orient_matrix_UB_22      0.0721727000
_diffrn_orient_matrix_UB_23      -0.0256002000
_diffrn_orient_matrix_UB_31      0.0640323000
_diffrn_orient_matrix_UB_32      0.0011277000
_diffrn_orient_matrix_UB_33      -0.0119112000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4203
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.892
_diffrn_reflns_theta_min         3.852
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method 'Recrystallized from methanol'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.447
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.2604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1833
_reflns_number_total             2244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00217b2.cif
_cod_data_source_block           exp_1254
_cod_depositor_comments
'Adding full bibliography for 7248586--7248590.cif.'
_cod_database_code               7248588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C9H10N2O2S
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H10 of C10
 At 1.5 times of:
  H12a of C12
2.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C3(H3a,H3b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2017-11-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.734