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_7248587
_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_absolute_configuration unk
_chemical_formula_moiety         'C9 H10 N2 O2 S'
_chemical_formula_sum            'C9 H10 N2 O2 S'
_chemical_formula_weight         210.26
_chemical_name_systematic        1-(5-methylthiazol-2-yl)piperidine-2,6-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-07 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            4
_cell_length_a                   17.3234(14)
_cell_length_b                   6.5197(5)
_cell_length_c                   8.7737(7)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0870
_cell_measurement_theta_min      3.8840
_cell_volume                     990.93(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.6917
_diffrn_measured_fraction_theta_max 0.6917
_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    -40.00  62.00   1.00    6.63    --   19.29 -19.00-120.00  102
  2  \w    -20.00   5.00   1.00    6.63    --  -20.23 -99.00  30.00   25
  3  \w    -59.00 -27.00   1.00    6.63    --  -20.23 -77.00 120.00   32
;
_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      0.0383344000
_diffrn_orient_matrix_UB_12      -0.0382432000
_diffrn_orient_matrix_UB_13      -0.0005215000
_diffrn_orient_matrix_UB_21      -0.0095829000
_diffrn_orient_matrix_UB_22      -0.0692225000
_diffrn_orient_matrix_UB_23      0.0594584000
_diffrn_orient_matrix_UB_31      -0.0107399000
_diffrn_orient_matrix_UB_32      -0.0746669000
_diffrn_orient_matrix_UB_33      -0.0547986000
_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  0.0241
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2748
_diffrn_reflns_theta_full        26.3584
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.4092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440.6876
_exptl_crystal_recrystallization_method 'Crystallised from Ethylacetate'
_exptl_crystal_size_max          0.925
_exptl_crystal_size_mid          0.638
_exptl_crystal_size_min          0.239
_refine_diff_density_max         0.2508
_refine_diff_density_min         -0.2623
_refine_diff_density_rms         0.0426
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_d_res_high            0.8004
_refine_ls_d_res_low             6.1640
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0658
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+0.6130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.339
_reflns_limit_h_max              21
_reflns_limit_h_min              -21
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              9
_reflns_limit_l_min              -10
_reflns_number_gt                1203
_reflns_number_total             1402
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00217b2.cif
_cod_data_source_block           exp_971
_cod_depositor_comments
'Adding full bibliography for 7248586--7248590.cif.'
_cod_original_cell_volume        990.93(13)
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7248587
_chemical_oxdiff_usercomment     'MYS 01'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_date_sample_data_collection 2016-12-02
_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 1.059
_oxdiff_exptl_absorpt_empirical_full_min 0.942