One-pot chemo/regio/stereoselective generation of library of functionalized spiro-oxindoles/pyrrolizines/pyrrolidines from α–aroylidineketene dithioacetals
SHANMUGAM, SIVAKUMAR; Pandi, Dhanalakshmi; Seenivasagaperumal, Sriram Babu; Thimmarayaperumal, Solaimalai; RSC Adv.  (2015) –; doi:10.1039/C5RA05123A

data_7220047
_publ_section_title
;
 One-pot chemo/regio/stereoselective generation of library of
 functionalized spiro-oxindoles/pyrrolizines/pyrrolidines from
 \a--aroylidineketene dithioacetals
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA05123A
_journal_year                    2015
_chemical_formula_moiety         'C25 H25 Br N2 O2 S2'
_chemical_formula_sum            'C25 H25 Br N2 O2 S2'
_chemical_formula_weight         529.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_update_record
;
2014-02-24 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                78.184(8)
_cell_angle_beta                 70.207(8)
_cell_angle_gamma                73.573(8)
_cell_formula_units_Z            2
_cell_length_a                   10.1343(15)
_cell_length_b                   11.2188(15)
_cell_length_c                   12.5542(19)
_cell_measurement_temperature    296(2)
_cell_volume                     1278.8(3)
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28989
_diffrn_reflns_theta_full        24.9970
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_process_details   empirical
_exptl_crystal_density_diffrn    1.3751
_exptl_crystal_F_000             544.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.7106
_refine_diff_density_min         -0.8420
_refine_diff_density_rms         0.0632
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             11.7260
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0181
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+0.8539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3644
_reflns_number_total             4493
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra05123a2.cif
_cod_data_source_block           spc1_0m
_cod_database_code               7220047
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H1 of N1, H22 of C22, H4 of C4, H20 of C20, {H11a,H11b} of C11,
  H18 of C18, H13 of C13, {H10a,H10b} of C10, H5 of C5, H16 of C16, {H9a,H9b}
  of C9, H3 of C3, H19 of C19, H15 of C15, H2 of C2
 At 1.5 times of:
  {H25a,H25b,H25c} of C25, {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C20(H20), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C11(H11a,H11b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C15(H15), C16(H16), C5(H5), C4(H4), C3(H3), C2(H2),
 N1(H1), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C25(H25a,H25b,H25c)
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