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_4036603
_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         'C25 H19 Cl N2 O2 S'
_chemical_formula_sum            'C25 H19 Cl N O2 S'
_chemical_formula_weight         432.92
_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                96.0030(10)
_cell_angle_beta                 104.1560(10)
_cell_angle_gamma                91.3710(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5557(2)
_cell_length_b                   10.2960(2)
_cell_length_c                   11.4909(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1088.76(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  monochromate
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            16328
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         1.84
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_correction_T_min  0.9173
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0052(18)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.2888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3912
_reflns_number_total             4474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02920_si_004.cif
_cod_data_source_block           fin1
_cod_database_code               4036603
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.066) H3(0.074) H4(0.071) H5(0.062) H11(0.056) H13(0.052)
 H14A(0.072) H14B(0.072) H15A(0.108) H15B(0.108) H15C(0.108) H16A(0.061)
 H16B(0.061) H19(0.056) H21(0.059) H22(0.066) H24(0.072) H25(0.065) H1(0.076)
 Fixed X: H2(-0.1592) H3(-0.1171) H4(0.0998) H5(0.2806) H11(0.4515)
 H13(0.1539) H14A(0.6899) H14B(0.5499) H15A(0.7836) H15B(0.7534) H15C(0.6454)
 H16A(0.1581) H16B(0.3203) H19(0.3936) H21(0.4856) H22(0.4899) H24(0.1567)
 H25(0.1507) H1(0.4109)
 Fixed Y: H2(0.7262) H3(0.692) H4(0.7589) H5(0.8639) H11(1.2055) H13(0.934)
 H14A(1.3057) H14B(1.3859) H15A(1.4166) H15B(1.5159) H15C(1.4986) H16A(0.9896)
 H16B(0.989) H19(1.1423) H21(1.2403) H22(1.3947) H24(1.5637) H25(1.4073)
 H1(1.0574)
 Fixed Z: H2(0.3989) H3(0.2092) H4(0.1751) H5(0.3301) H11(1.0603) H13(0.8695)
 H14A(1.046) H14B(1.0166) H15A(0.9113) H15B(1.0143) H15C(0.8862) H16A(1.0727)
 H16B(1.1436) H19(1.3046) H21(1.4957) H22(1.6571) H24(1.4547) H25(1.2939)
 H1(0.6237)
;