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_7220049
_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 N3 O4 S2'
_chemical_formula_sum            'C25 H25 Br N3 O4 S2'
_chemical_formula_weight         575.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_audit_update_record
;
2014-02-24 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.463(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2286(12)
_cell_length_b                   9.6157(6)
_cell_length_c                   30.5098(19)
_cell_measurement_temperature    296(2)
_cell_volume                     5154.2(6)
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            113097
_diffrn_reflns_theta_full        25.9986
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_process_details   empirical
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             2360.00
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.9979
_refine_diff_density_min         -0.9954
_refine_diff_density_rms         0.1124
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             13.5726
_refine_ls_goodness_of_fit_ref   1.0506
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    86
_refine_ls_number_parameters     634
_refine_ls_number_reflns         10142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0506
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+4.8099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -22
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              -15
_reflns_number_gt                7147
_reflns_number_total             10142
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra05123a2.cif
_cod_data_source_block           SCP4_0m
_cod_database_code               7220049
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1l of C1l, H1k of C1k, H5a of N5, H5 of C5, H19 of C19, H1r of C1r, H1b of
  C1b, H1q of C1q, H1j of C1j, {H32a,H32b} of C32, {H1pa,H1pb} of C1p, H25 of
  C25, H1n of C1n, H23 of C23, {H34a,H34b} of C34, H26 of C26, H7 of N7, {H1ga,
  H1gb} of C1g, H20 of C20, H11 of C11, H1i of C1i, H27 of C27, {H1ma,H1mb} of
  C1m, H1f of C1f, H15 of C15, H24 of C24, H8 of N8, H10 of C10, H9 of C9, H4
  of N4, {H1oa,H1ob} of C1o, H1a of C1a
 At 1.5 times of:
  {H29a,H29b,H29c} of C29, {H30a,H30b,H30c} of C30, {H1ha,H1hb,H1hc} of C1h,
  {H28a,H28b,H28c} of C28
2.a Ternary CH refined with riding coordinates:
 N4(H4), N7(H7), C9(H9), C11(H11), C5(H5), C10(H10), C15(H15), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1g(H1ga,H1gb), C1m(H1ma,H1mb), C1o(H1oa,H1ob), C1p(H1pa,H1pb), C32(H32a,
 H32b), C34(H34a,H34b)
2.c Aromatic/amide H refined with riding coordinates:
 C1l(H1l), C26(H26), C25(H25), C1j(H1j), C1i(H1i), C27(H27), C23(H23),
 C24(H24), C1r(H1r), C1q(H1q), C1f(H1f), C1k(H1k), C1n(H1n), C20(H20), N5(H5a),
 N8(H8), C1a(H1a), C1b(H1b)
2.d Idealised Me refined as rotating group:
 C1h(H1ha,H1hb,H1hc), C28(H28a,H28b,H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,
 H30c)
;