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_4036602
_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         'C24 H17 N O2 S'
_chemical_formula_sum            'C24 H17 N O2 S'
_chemical_formula_weight         383.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90.00
_cell_angle_beta                 114.5970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4196(2)
_cell_length_b                   20.2974(5)
_cell_length_c                   10.6385(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1849.44(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  monochromate
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17498
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0746P)^2^+0.3713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                3824
_reflns_number_total             4642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02920_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4036602
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.063) H3(0.07) H4(0.069) H5(0.063) H9(0.054) H10(0.061)
 H11(0.055) H16A(0.076) H16B(0.076) H17(0.046) H19(0.07) H20(0.093) H21(0.098)
 H22(0.087) H24A(0.103) H24B(0.103) H24C(0.103)
 Fixed X: H2(-0.1469) H3(-0.2944) H4(-0.1983) H5(0.0493) H9(0.5136) H10(0.752)
 H11(0.8436) H16A(0.4833) H16B(0.6465) H17(0.7813) H19(1.0099) H20(1.1872)
 H21(1.1128) H22(0.8626) H24A(0.582) H24B(0.6218) H24C(0.5506)
 Fixed Y: H2(0.4788) H3(0.5738) H4(0.6726) H5(0.6796) H9(0.5956) H10(0.5738)
 H11(0.4671) H16A(0.2221) H16B(0.2356) H17(0.3466) H19(0.3149) H20(0.2948)
 H21(0.3065) H22(0.336) H24A(0.3991) H24B(0.3832) H24C(0.3285)
 Fixed Z: H2(0.7062) H3(0.6405) H4(0.7486) H5(0.9241) H9(1.2181) H10(1.3954)
 H11(1.4409) H16A(1.2582) H16B(1.3891) H17(1.2581) H19(1.4171) H20(1.6405)
 H21(1.8194) H22(1.7761) H24A(1.477) H24B(1.6323) H24C(1.5194)
;