Synthesis of Isomeric Isothiazolo[4′,3′:4,5]- and Isothiazolo[4′,5′:4,5]thieno[3,2-b]pyrano[2,3-d]pyridines by Combination of Domino Reactions
Shestopalov, Anatoliy M.; Larionova, Natalia A.; Fedorov, Alexander E.; Rodinovskaya, Lyudmila A.; Mortikov, Valery Yu.; Zubarev, Andrey A.; Bushmarinov, Ivan S.; ACS Combinatorial Science 15 (2013) 541–; doi:10.1021/co400066y

data_4508360
_publ_section_title
;
 Synthesis of Isomeric Isothiazolo[4&#x2032;,3&#x2032;:4,5]- and
 Isothiazolo[4&#x2032;,5&#x2032;:4,5]thieno[3,2-b]pyrano[2,3-d]pyridines
 by Combination of Domino Reactions
;
_journal_issue                   10
_journal_name_full               'ACS Combinatorial Science'
_journal_page_first              541
_journal_paper_doi               10.1021/co400066y
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C11 H12 N2 O3 S3'
_chemical_formula_sum            'C11 H12 N2 O3 S3'
_chemical_formula_weight         316.41
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-08-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.849(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.160(5)
_cell_length_b                   4.6826(11)
_cell_length_c                   13.811(3)
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    300
_cell_measurement_theta_max      64.885
_cell_measurement_theta_min      3.874
_cell_volume                     1475.7(6)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10726
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.030
_diffrn_reflns_theta_min         3.874
_diffrn_source                   'microfocus tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.653
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1222 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8290.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'grayish yellow'
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method 'crystallized from ???'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0928P)^2^+0.5820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1687
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co400066y_si_001.cif
_cod_data_source_block           4b
_cod_database_code               4508360
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9'-C8
 1.5 with sigma of 0.01
 C9'-C8 = C9-C8
 1.5 with sigma of 0.01
 O3-C9 = O3'-C9'
 1.33 with sigma of 0.01
 O2'-C9' = O2-C9
 1.2 with sigma of 0.01
 C11'-C10' = C11-C10
 1.5 with sigma of 0.02
 O3-C10 = O3'-C10'
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O2 \\sim C9 \\sim C9' \\sim O2' \\sim O3 \\sim O3' \\sim C10' \\sim C10 \\sim C11' \\sim C11: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H8BC)=Sof(H8BD)=Sof(C9')=Sof(O3')=Sof(O2')=Sof(C11')=Sof(H11A)=Sof(H11B)=
 Sof(H11C)=Sof(C10')=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(C9)=Sof(O3)=Sof(O2)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C11)=Sof(H11D)=Sof(H11E)=Sof(H11F)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8BC,H8BD), C8(H8AA,H8AB), C10(H10A,H10B), C10'(H10C,H10D)
5.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C11'(H11A,H11B,H11C), C11(H11D,H11E,H11F)
;
_shelx_hkl_checksum              86744
_shelx_res_checksum              7902
_shelxl_version_number           2013-4