One-Pot Synthesis of Benzothiazole-Tethered Chromanones/Coumarins via Claisen Rearrangement Using the Solid State Melt Reaction.
Bakthadoss, Manickam; Selvakumar, Raman; The Journal of organic chemistry 81 (2016) 3391–3399; doi:10.1021/acs.joc.5b02920

data_4036604
_publ_section_title
;
 One-Pot Synthesis of Benzothiazole-Tethered Chromanones/Coumarins via
 Claisen Rearrangement Using the Solid State Melt Reaction.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3391
_journal_page_last               3399
_journal_paper_doi               10.1021/acs.joc.5b02920
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C26 H21 N O2 S'
_chemical_formula_sum            'C26 H21 N O2 S'
_chemical_formula_weight         411.50
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                95.821(2)
_cell_angle_beta                 97.715(2)
_cell_angle_gamma                93.790(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7107(2)
_cell_length_b                   10.3413(3)
_cell_length_c                   11.8345(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1047.51(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  monochromate
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0216
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15798
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourlecc
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0994P)^2^+0.8129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2141
_reflns_number_gt                3292
_reflns_number_total             4259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02920_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4036604
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H26A(0.375) H26B(0.375) H26C(0.375) H2(0.113) H3(0.131) H4(0.132)
 H5(0.115) H9(0.082) H10(0.089) H11(0.076) H16A(0.111) H16B(0.111) H16C(0.111)
 H19(0.085) H20(0.094) H22(0.088) H23(0.075) H24(0.149) H25A(0.482) H25B(0.482)
 H25C(0.482)
 Fixed X: H26A(-0.7934) H26B(-0.8668) H26C(-0.7596) H2(0.6804) H3(0.9187)
 H4(0.9703) H5(0.7902) H9(0.3354) H10(0.1309) H11(-0.0821) H16A(-0.3578) H16B(-
 0.2439) H16C(-0.3299) H19(-0.3658) H20(-0.5653) H22(-0.4082) H23(-0.2122) H24(-
 0.5953) H25A(-0.7868) H25B(-0.6913) H25C(-0.6142)
 Fixed Y: H26A(0.3318) H26B(0.2883) H26C(0.4183) H2(0.9271) H3(1.021)
 H4(1.0428) H5(0.9774) H9(0.78) H10(0.6749) H11(0.5826) H16A(0.5055)
 H16B(0.5088) H16C(0.6326) H19(0.6426) H20(0.5155) H22(0.2008) H23(0.3269)
 H24(0.2342) H25A(0.1545) H25B(0.0788) H25C(0.1279)
 Fixed Z: H26A(0.9335) H26B(0.8058) H26C(0.8368) H2(0.5245) H3(0.6183)
 H4(0.8132) H5(0.9236) H9(0.9784) H10(1.0468) H11(0.9225) H16A(0.5192)
 H16B(0.4274) H16C(0.4606) H19(0.8167) H20(0.8677) H22(0.7183) H23(0.6608)
 H24(0.9119) H25A(0.7321) H25B(0.8222) H25C(0.7204)
;