Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
Thangamani, Murugesan; Thangamalar, Subaramaniam; Srinivasan, Kannupal; RSC Advances 11 (2021) 14980–14985; doi:10.1039/D1RA01194D

data_7242691
_publ_section_title
;
 Tin(iv) chloride mediated (3 + 2) annulation of
 trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles:
 diastereoselective access to 5-vinyl-1-pyrroline derivatives
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              14980
_journal_page_last               14985
_journal_paper_doi               10.1039/D1RA01194D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C32 H33 N O6'
_chemical_formula_sum            'C32 H33 N O6'
_chemical_formula_weight         527.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc26rtvn
_audit_creation_date             2020-11-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-02 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0422(6)
_cell_length_b                   22.1419(14)
_cell_length_c                   26.2315(15)
_cell_measurement_reflns_used    100421
_cell_measurement_temperature    298.08
_cell_measurement_theta_max      30.071
_cell_measurement_theta_min      2.358
_cell_volume                     5832.7(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.08
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            100421
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.071
_diffrn_reflns_theta_min         2.358
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         100421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.6975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                44246
_reflns_number_total             100421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra01194d2.cif
_cod_data_source_block           bm1a_13112019_0m_a
_cod_database_code               7242691
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(10)
 1(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Fixed Sof: H20A(0.6) H20B(0.6) H20C(0.4) H20D(0.4) C21B(0.4) H21A(0.4)
 H21B(0.4) H21C(0.4) C21A(0.6) H21D(0.6) H21E(0.6) H21F(0.6)
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C10(H10), C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20(H20C,H20D), C23(H23A,H23B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C27(H27), C28(H28), C30(H30), C31(H31)
4.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C32(H32A,H32B,H32C), C21B(H21A,H21B,H21C), C21A(H21D,
 H21E,H21F)
;
_shelx_res_checksum              62963
_olex2_submission_special_instructions 'No special instructions were received'