Solvent-free iodine-promoted synthesis of 3,2′-pyrrolinyl spirooxindoles from alkylidene oxindoles and enamino esters under ball-milling conditions
Xu, Hui; Liu, Hong-Wei; Lin, Hao-Sheng; Wang, Guan-Wu; Chemical Communications  (2017) –; doi:10.1039/C7CC08306H

data_7120846
_publ_section_title
;
 Solvent-free iodine-promoted synthesis of 3,2&#x2032;-pyrrolinyl
 spirooxindoles from alkylidene oxindoles and enamino esters under
 ball-milling conditions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC08306H
_journal_year                    2017
_chemical_formula_sum            'C30 H34 N2 O6'
_chemical_formula_weight         518.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1p95nt
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-23 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.9450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.13730(10)
_cell_length_b                   24.0612(2)
_cell_length_c                   11.22560(10)
_cell_measurement_reflns_used    15648
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.2110
_cell_measurement_theta_min      4.3150
_cell_volume                     2770.19(5)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24796
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.338
_diffrn_reflns_theta_min         3.674
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00141(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.7183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4877
_reflns_number_total             5269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08306h2.cif
_cod_data_source_block           shelxl
_cod_database_code               7120846
_shelx_estimated_absorpt_t_min   0.849
_shelx_estimated_absorpt_t_max   0.889
_shelxl_version_number           2013-4
_shelx_res_checksum              55024