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_7248589
_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         'C10 H12 N2 O2 S'
_chemical_formula_sum            'C10 H12 N2 O2 S'
_chemical_formula_weight         224.28
_chemical_name_systematic
1-(4,5-dimethylthiazol-2-yl)piperidine-2,6-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0048(7)
_cell_length_b                   9.1927(7)
_cell_length_c                   21.2407(14)
_cell_measurement_reflns_used    1575
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1710
_cell_measurement_theta_min      4.0720
_cell_volume                     2148.8(3)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_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    -12.00  86.00   1.00    4.13    --   19.44  77.00 -30.00   98
  2  \w    -52.00 -26.00   1.00    4.13    --  -20.23  77.00  90.00   26
  3  \w     10.00  40.00   1.00    4.13    --  -20.23  77.00  90.00   30
  4  \w    -11.00  34.00   1.00    4.13    --  -20.23  77.00-120.00   45
;
_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      -0.0436994000
_diffrn_orient_matrix_UB_12      -0.0148706000
_diffrn_orient_matrix_UB_13      -0.0237001000
_diffrn_orient_matrix_UB_21      0.0465300000
_diffrn_orient_matrix_UB_22      0.0006254000
_diffrn_orient_matrix_UB_23      -0.0231319000
_diffrn_orient_matrix_UB_31      0.0089216000
_diffrn_orient_matrix_UB_32      -0.0756383000
_diffrn_orient_matrix_UB_33      0.0044855000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91031
_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 yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method 'Recrystallized from Ethylacetate'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.683
_exptl_crystal_size_min          0.301
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             2560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00217b2.cif
_cod_data_source_block           exp_1313
_cod_depositor_comments
'Adding full bibliography for 7248586--7248590.cif.'
_cod_database_code               7248589
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.785
_diffrn_oxdiff_ac3_digest_frames
;
01a7d72e76aae5cb283ea2b7d237751d3300027a857
;
_diffrn_oxdiff_ac3_digest_hkl
;
0169753652c2b31d3599ff5f599b7603fb981d
;
_reflns_odcompleteness_completeness 99.45
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00C,H00D), C00D(H00E,H00F)
2.b Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I), C00F(H00J,H00K,H00L)
;
_olex2_date_sample_data_collection 2017-12-26
_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.871