[3+3] Annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes
Gopal Sathishkannan; Kannupal Srinivasan; Chem.Commun. 50 (2014) 4062–; doi:10.1039/C4CC00565A

data_7112209
_publ_section_title
;
 [3+3] Annulation of donor-acceptor cyclopropanes with
 mercaptoacetaldehyde: application to the synthesis of tetrasubstituted
 thiophenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              4062
_journal_paper_doi               10.1039/C4CC00565A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C22 H22 O6 S'
_chemical_formula_sum            'C22 H22 O6 S'
_chemical_formula_weight         414.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-14
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.99(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.107(3)
_cell_length_b                   8.543(3)
_cell_length_c                   34.204(8)
_cell_measurement_reflns_used    860
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7056
_cell_measurement_theta_min      3.8203
_cell_volume                     2065.4(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9892
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details
;
  1 omega  -11.00   20.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000 -120.0000 31

  2 omega  -46.00  -21.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   77.0000 -120.0000 25

  3 omega    0.00   50.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   77.0000 -120.0000 50

  4 omega  -61.00  -35.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522 -178.0000  -60.0000 26

  5 omega  -84.00  -54.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  178.0000   90.0000 30

  6 omega  -25.00    0.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000    0.0000 25

  7 omega  -25.00   10.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000  150.0000 35

  8 omega  -33.00   27.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   57.0000    0.0000 60

  9 omega  -86.00  -51.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -57.0000 -180.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0879032000
_diffrn_orient_matrix_UB_12      0.0373625000
_diffrn_orient_matrix_UB_13      -0.0050110000
_diffrn_orient_matrix_UB_21      -0.0098904000
_diffrn_orient_matrix_UB_22      -0.0414360000
_diffrn_orient_matrix_UB_23      -0.0182393000
_diffrn_orient_matrix_UB_31      -0.0464664000
_diffrn_orient_matrix_UB_32      -0.0620907000
_diffrn_orient_matrix_UB_33      0.0087113000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            11955
_diffrn_reflns_theta_full        29.77
_diffrn_reflns_theta_max         29.77
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.672
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+1.1483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1420
_reflns_number_gt                2950
_reflns_number_total             4782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00565a2.cif
_cod_data_source_block           ndr-km
_cod_original_cell_volume        2065.3(13)
_cod_database_code               7112209
_chemical_oxdiff_formula         'C20 H20 O2 S1'
_chemical_oxdiff_usercomment     '298K, COLORLESS BLOCK, 0.4 0.3 0.2'
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32