A Catalyst-Free Facile Synthesis of 2-(dihydropyridyl)benzothiazoles from (Benzothiazol-2-yl)acrylonitriles: A Green Route
Singh, Nikunj; Budhwan, Rajnish; Rawat, Megha; Peddinti, Rama Krishna; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00288A

data_7161081
_publ_section_title
;
 Catalyst-free facile synthesis of 2-(dihydropyridyl)benzothiazoles from
 (benzothiazol-2-yl)acrylonitriles: green route.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3210
_journal_page_last               3217
_journal_paper_doi               10.1039/d6ob00288a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C21 H16 F3 N5 O2 S, C2 H6 O S'
_chemical_formula_sum            'C23 H22 F3 N5 O3 S2'
_chemical_formula_weight         537.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-10-27
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-27 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                94.609(9)
_cell_angle_beta                 110.349(9)
_cell_angle_gamma                108.894(9)
_cell_formula_units_Z            2
_cell_length_a                   9.845(4)
_cell_length_b                   11.454(4)
_cell_length_c                   12.044(4)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.8405
_cell_measurement_theta_min      2.4346
_cell_volume                     1175.9(8)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST photon III C7'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.849
_diffrn_reflns_theta_min         1.925
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.084
_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     327
_refine_ls_number_reflns         4525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0866P)^2^+0.5485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4114
_reflns_number_total             4525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00288a2.cif
_cod_data_source_block           rkp_ns_th11_1977_0ma_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7161079--7161081.cif.
;
_cod_original_cell_volume        1176.0(7)
_cod_database_code               7161081
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C3(H3), C4(H4A), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              67527
_olex2_submission_special_instructions 'No special instructions were received'