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_4508359
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.650(4)
_cell_length_b                   13.822(11)
_cell_length_c                   21.585(17)
_cell_measurement_reflns_used    1190
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.040
_cell_measurement_theta_min      2.394
_cell_volume                     1387(2)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2069
_diffrn_reflns_av_unetI/netI     0.1675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12649
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.887
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0817 after correction.
The Ratio of minimum to maximum transmission is 0.5523.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method 'crystallized from ???'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0185P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1570
_reflns_number_total             2833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co400066y_si_001.cif
_cod_data_source_block           4a
_cod_original_cell_volume        1387.3(19)
_cod_database_code               4508359
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C11(H11A,H11B,H11C)
;
_shelx_hkl_checksum              23390
_shelx_res_checksum              29647
_shelxl_version_number           2013-4