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_7220050
_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         'C30 H29 Br N2 O3 S2'
_chemical_formula_sum            'C30 H29 Br N2 O3 S2'
_chemical_formula_weight         609.61
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-12-21 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                88.602(2)
_cell_angle_beta                 77.468(2)
_cell_angle_gamma                84.525(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4344(6)
_cell_length_b                   12.6293(9)
_cell_length_c                   15.4003(11)
_cell_measurement_reflns_used    9236
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.12
_cell_volume                     1405.05(18)
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9833
_diffrn_measured_fraction_theta_max 0.9833
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34824
_diffrn_reflns_theta_full        27.6008
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.646
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5631
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.7552.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.4408
_exptl_crystal_description       sheet
_exptl_crystal_F_000             628.1698
_refine_diff_density_max         1.4192
_refine_diff_density_min         -1.2790
_refine_diff_density_rms         0.2339
_refine_ls_d_res_high            0.7670
_refine_ls_d_res_low             6.5310
_refine_ls_goodness_of_fit_ref   0.8957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8957
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.0336
_refine_ls_shift/su_mean         0.0015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3461
_reflns_number_total             6418
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra05123a2.cif
_cod_data_source_block           pa_0m
_cod_database_code               7220050
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C27(H27), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C25(H25), C11(H11), C31(H31), C37(H37), C33(H33), C21(H21),
 C16(H16), C30(H30), C22(H22), C28(H28), C10(H10), N8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C34(H34a,H34b,H34c), C38(H38a,H38b,H38c), C1(H1a,H1b,H1c)
;