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_7161079
_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         'C19 H16 N6 O2 S, C2 H6 O S'
_chemical_formula_sum            'C21 H22 N6 O3 S2'
_chemical_formula_weight         470.56
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-24 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.871(9)
_cell_angle_beta                 93.284(9)
_cell_angle_gamma                110.537(8)
_cell_formula_units_Z            2
_cell_length_a                   8.725(2)
_cell_length_b                   9.713(2)
_cell_length_c                   13.679(3)
_cell_measurement_reflns_used    9695
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.49
_cell_volume                     1064.8(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            67161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.656
_diffrn_reflns_theta_min         2.279
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7045
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1118 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.9451.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0497P)^2^+0.4480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4012
_reflns_number_total             4419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00288a2.cif
_cod_data_source_block           rkp_ns_py4_2315_0m
_cod_depositor_comments
'Adding full bibliography for 7161079--7161081.cif.'
_cod_database_code               7161079
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.884
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N008(H00A)
2.b Ternary CH refined with riding coordinates:
 C00L(H00L)
2.c Secondary CH2 refined with riding coordinates:
 C00K(H00C,H00D), C00O(H00E,H00F)
2.d Aromatic/amide H refined with riding coordinates:
 N007(H007), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00V(H00V)
2.e Idealised Me refined as rotating group:
 C00T(H00G,H00H,H00I), C00W(H00J,H00K,H00O)
;
_shelx_res_checksum              41944
_olex2_submission_special_instructions 'No special instructions were received'