Highly Diastereoselective Synthesis of Benzothiazolo[3,2-a]pyridines via [4 + 2] Annulation Reaction of 2-Vinylbenzothiazoles and Azlactones
Pan, Bin; Li, Ao; Liu, Dong; Ni, QingShan; Liang, Wu; Du, Fei; Gu, Jing; ouyang, qin; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00618A

data_7158688
_publ_section_title
;
 Highly Diastereoselective Synthesis of Benzothiazolo[3,2-a]pyridines via
 [4 + 2] Annulation Reaction of 2-Vinylbenzothiazoles and Azlactones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00618A
_journal_year                    2022
_chemical_formula_moiety         'C26 H18 Cl N3 O2 S, C H2 Cl2'
_chemical_formula_sum            'C27 H20 Cl3 N3 O2 S'
_chemical_formula_weight         556.87
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-27 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                72.079(5)
_cell_angle_beta                 78.101(5)
_cell_angle_gamma                83.806(5)
_cell_formula_units_Z            2
_cell_length_a                   10.2432(6)
_cell_length_b                   11.1049(6)
_cell_length_c                   11.6840(6)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3910
_cell_measurement_theta_min      3.6350
_cell_volume                     1235.98(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_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      3.00  77.00   1.00    4.75    --   18.58-126.00 -27.01   74
  2  \w     -9.00  89.00   1.00    4.75    --   18.58  77.00-180.00   98
  3  \w    -42.00  49.00   1.00    4.75    --   18.58 -77.00-180.00   91
  4  \w     -9.00  89.00   1.00    4.75    --   18.58  77.00 -60.00   98
  5  \w    -50.00  40.00   1.00    4.75    --   18.58 -57.00 -60.00   90
  6  \w     14.00  87.00   1.00    4.75    --   18.58  57.00  90.00   73
  7  \w     29.00  60.00   1.00    4.75    --   18.58 -99.00  90.00   31
  8  \w    -85.00 -11.00   1.00    4.75    --  -18.81 -77.00  30.00   74
  9  \w    -44.00  53.00   1.00    4.75    --  -18.81  38.00  90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0221482000
_diffrn_orient_matrix_UB_12      0.0627415000
_diffrn_orient_matrix_UB_13      -0.0238177000
_diffrn_orient_matrix_UB_21      -0.0672176000
_diffrn_orient_matrix_UB_22      0.0239162000
_diffrn_orient_matrix_UB_23      0.0017380000
_diffrn_orient_matrix_UB_31      -0.0032560000
_diffrn_orient_matrix_UB_32      0.0028665000
_diffrn_orient_matrix_UB_33      0.0603432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18501
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0452P)^2^+0.4917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4391
_reflns_number_total             5865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00618a2.cif
_cod_data_source_block           20210414-ouyang-pb-934
_cod_database_code               7158688
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H18 Cl N3 O2 S'
_reflns_odcompleteness_completeness 99.78
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C12(H12), C16(H16), C15(H15), C13(H13), C2(H2), C26(H26), C5(H5),
 C22(H22), C3(H3A), C4(H4), C25(H25), C24(H24), C23(H23)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              76747
_olex2_date_sample_data_collection 2021-04-14
_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 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.748