#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:36:09 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/85/7248590.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248590
loop_
_publ_author_name
'Shaiwale, Mayuri'
'Som, Narayan N.'
'Jha, Prafulla K.'
'Ballabh, Amar'
_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         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.28
_chemical_name_systematic        1-(benzo[d]thiazol-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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-07
_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            8
_cell_length_a                   10.7717(9)
_cell_length_b                   9.2453(9)
_cell_length_c                   23.0901(14)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9390
_cell_measurement_theta_min      4.0250
_cell_volume                     2299.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  51.00   1.00    1.96    --   19.29 -77.00-150.00  103
  2  ω     -8.00  92.00   1.00    1.96    --   19.29  38.00-180.00  100
  3  ω    -25.00  23.00   1.00    1.96    --  -20.38 -99.00  90.00   48
  4  ω    -50.00  25.00   1.00    1.96    --   19.29 -57.00  30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0386603000
_diffrn_orient_matrix_UB_12      0.0008188000
_diffrn_orient_matrix_UB_13      -0.0248868000
_diffrn_orient_matrix_UB_21      0.0532193000
_diffrn_orient_matrix_UB_22      0.0058936000
_diffrn_orient_matrix_UB_23      -0.0179164000
_diffrn_orient_matrix_UB_31      0.0036914000
_diffrn_orient_matrix_UB_32      -0.0764738000
_diffrn_orient_matrix_UB_33      -0.0016728000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12233
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.398
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method 'Crystallised from Metjhanol'
_exptl_crystal_size_max          1.26
_exptl_crystal_size_mid          0.693
_exptl_crystal_size_min          0.346
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          13.373
_refine_ls_shift/su_mean         0.086
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1510P)²+2.6040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1862
_reflns_number_total             2341
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00217b2.cif
_cod_data_source_block           exp_1166
_cod_depositor_comments
'Adding full bibliography for 7248586--7248590.cif.'
_cod_database_code               7248590
_shelx_shelxl_version_number     2014/7
_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.
;
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C7(H7), C5(H5)
;
_olex2_date_sample_data_collection 2017-06-28
_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 1.898
_oxdiff_exptl_absorpt_empirical_full_min 0.667
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
S2 S 0.28006(9) 0.02123(12) 0.60525(4) 0.0606(4) Uani 1 1 d . . . . .
N10 N 0.3795(2) -0.0653(3) 0.70861(10) 0.0407(6) Uani 1 1 d . . . . .
O17 O 0.2178(3) -0.2182(3) 0.72103(11) 0.0673(8) Uani 1 1 d . . . . .
N9 N 0.4414(3) -0.1819(3) 0.62183(11) 0.0501(7) Uani 1 1 d . . . . .
C1 C 0.3748(3) -0.0875(3) 0.64759(12) 0.0403(7) Uani 1 1 d . . . . .
C11 C 0.2923(3) -0.1391(3) 0.74322(13) 0.0455(7) Uani 1 1 d . . . . .
C16 C 0.4733(3) 0.0269(4) 0.72898(15) 0.0479(8) Uani 1 1 d . . . . .
O18 O 0.5414(2) 0.0850(3) 0.69463(12) 0.0676(8) Uani 1 1 d . . . . .
C3 C 0.3348(3) -0.0703(4) 0.54527(13) 0.0520(8) Uani 1 1 d . . . . .
C8 C 0.4201(3) -0.1746(4) 0.56241(14) 0.0508(8) Uani 1 1 d . . . . .
C6 C 0.4537(5) -0.2361(6) 0.46375(18) 0.0865(15) Uani 1 1 d . . . . .
H6 H 0.4925 -0.2922 0.4356 0.104 Uiso 1 1 calc R . . . .
C12 C 0.2997(4) -0.1117(6) 0.80722(15) 0.0630(10) Uani 1 1 d . . . . .
C15 C 0.4818(4) 0.0464(6) 0.79274(18) 0.0771(14) Uani 1 1 d . . . . .
C4 C 0.3091(4) -0.0481(5) 0.48660(16) 0.0747(12) Uani 1 1 d . . . . .
H4 H 0.2518 0.0212 0.4749 0.090 Uiso 1 1 calc R . . . .
C7 C 0.4807(5) -0.2599(5) 0.52085(18) 0.0762(12) Uani 1 1 d . . . . .
H7 H 0.5376 -0.3305 0.5318 0.091 Uiso 1 1 calc R . . . .
C5 C 0.3706(5) -0.1312(6) 0.44681(16) 0.0849(16) Uani 1 1 d . . . . .
H5 H 0.3559 -0.1165 0.4076 0.102 Uiso 1 1 calc R . . . .
H15A H 0.550(5) 0.080(5) 0.8029(19) 0.074(14) Uiso 1 1 d . . . . .
H12A H 0.225(6) -0.134(7) 0.821(3) 0.12(2) Uiso 1 1 d . . . . .
C0AA C 0.4199(14) -0.0391(12) 0.8267(3) 0.187(6) Uani 1 1 d . . . . .
H0AA H 0.347(2) 0.019(3) 0.8248(12) -0.001(6) Uiso 1 1 d . . . . .
H12B H 0.318(7) -0.204(8) 0.821(3) 0.13(2) Uiso 1 1 d . . . . .
H15B H 0.412(16) 0.14(2) 0.810(7) 0.41(9) Uiso 1 1 d . . . . .
H0AB H 0.400(5) 0.004(6) 0.871(2) 0.105(16) Uiso 1 1 d . . . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C3 S2 C1 88.11(15) . . ?
C11 N10 C1 117.9(2) . . ?
C11 N10 C16 125.7(3) . . ?
C16 N10 C1 116.4(2) . . ?
C1 N9 C8 109.5(3) . . ?
N10 C1 S2 119.6(2) . . ?
N9 C1 S2 117.7(2) . . ?
N9 C1 N10 122.7(3) . . ?
N10 C11 C12 116.2(3) . . ?
O17 C11 N10 119.9(3) . . ?
O17 C11 C12 123.9(3) . . ?
N10 C16 C15 116.7(3) . . ?
O18 C16 N10 119.2(3) . . ?
O18 C16 C15 124.1(4) . . ?
C8 C3 S2 109.7(2) . . ?
C8 C3 C4 120.6(4) . . ?
C4 C3 S2 129.7(3) . . ?
C3 C8 N9 115.0(3) . . ?
C7 C8 N9 124.7(4) . . ?
C7 C8 C3 120.2(3) . . ?
C7 C6 C5 121.7(4) . . ?
C0AA C12 C11 114.1(4) . . ?
C0AA C15 C16 119.5(5) . . ?
C5 C4 C3 118.2(4) . . ?
C6 C7 C8 118.0(5) . . ?
C4 C5 C6 121.3(4) . . ?
C15 C0AA C12 121.8(6) . . ?
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
S2 C1 1.735(3) . ?
S2 C3 1.727(3) . ?
N10 C1 1.425(4) . ?
N10 C11 1.409(4) . ?
N10 C16 1.404(4) . ?
O17 C11 1.201(4) . ?
N9 C1 1.276(4) . ?
N9 C8 1.393(4) . ?
C11 C12 1.501(4) . ?
C16 O18 1.206(4) . ?
C16 C15 1.486(5) . ?
C3 C8 1.389(5) . ?
C3 C4 1.398(5) . ?
C8 C7 1.404(5) . ?
C6 C7 1.368(6) . ?
C6 C5 1.377(7) . ?
C12 C0AA 1.525(11) . ?
C15 C0AA 1.298(9) . ?
C4 C5 1.368(7) . ?
