Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation and Aromatization Cascade Reaction of β'-Acetoxy Allenoate and 1,2-Bisnucleophile.
Ni, Chunjie; Wang, MingLi; Tong, Xiaofeng; Organic letters 18 (2016) 2240–2243; doi:10.1021/acs.orglett.6b00874

data_1555554
_publ_section_title
;
 Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation
 and Aromatization Cascade Reaction of \b'-Acetoxy Allenoate and
 1,2-Bisnucleophile.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2240
_journal_page_last               2243
_journal_paper_doi               10.1021/acs.orglett.6b00874
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C14 H12 O3 S)'
_chemical_formula_sum            'C28 H24 O6 S2'
_chemical_formula_weight         520.59
_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
_audit_creation_date             2016-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.413(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.268(3)
_cell_length_b                   7.4469(12)
_cell_length_c                   22.374(4)
_cell_measurement_reflns_used    7104
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.675
_cell_measurement_theta_min      2.715
_cell_volume                     2540.3(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16735
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.424
_diffrn_reflns_theta_min         1.336
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1256 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8225.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+0.0931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4623
_reflns_number_total             6444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00874_si_002.cif
_cod_data_source_block           1
_cod_database_code               1555554
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C25(H25)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              74690
_shelx_hkl_checksum              79759
_olex2_submission_special_instructions 'No special instructions were received'