Green synthesis of new pyrrolidine-fused spirooxindoles via three-component domino reaction in EtOH/H2O
Wang, Yong-Chao; Wang, Jun-Liang; Burgess, Kevin S.; Zhang, Jiang-Wei; Zheng, Qiu-Mei; Pu, Ya-Dan; Yan, Li-Jun; Chen, Xue-Bing; RSC Advances 8 (2018) 5702–; doi:10.1039/C7RA13207G

data_7230077
_publ_section_title
;
 Green synthesis of new pyrrolidine-fused spirooxindoles via
 three-component domino reaction in EtOH/H2O
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              5702
_journal_paper_doi               10.1039/C7RA13207G
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C28 H30 N4 O4'
_chemical_formula_sum            'C28 H30 N4 O4'
_chemical_formula_weight         486.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-18 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.979(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8684(9)
_cell_length_b                   25.4867(18)
_cell_length_c                   10.5567(9)
_cell_measurement_reflns_used    6437
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      2.905
_cell_volume                     2479.1(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12158
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.905
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorness
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1030
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         7554
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.722
_reflns_Friedel_fraction_max     0.722
_reflns_number_gt                7437
_reflns_number_total             7554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra13207g2.cif
_cod_data_source_block           180115
_cod_depositor_comments
;

2018-02-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C28 H30 N4 O4)'
_cod_original_formula_sum        'C58 H62 N6 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     971.13
_cod_database_code               7230077
_shelx_shelxl_version_number     2016/6
_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:
 C19(H19), C48(H48), C38(H38), C57(H57), C29(H29), C50(H50), C22(H22),
 C20(H20), C52(H52), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C23(H23A,H23B), C54(H54A,H54B), C51(H51A,H51B), C25(H25A,
 H25B), C27(H27A,H27B), C53(H53A,H53B), C26(H26A,H26B), C56(H56A,H56B),
 C55(H55A,H55B)
2.c Aromatic/amide H refined with riding coordinates:
 C46(H46), C3(H3), C33(H33), C41(H41), C44(H44), N5(H5), N1(H1), C15(H15),
 C34(H34), C12(H12), C13(H13), C42(H42), C4(H4), C17(H17), C43(H43), C5(H5A),
 C14(H14), C32(H32)
2.d Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C18(H18A,H18B,H18C), C1(H1A,H1B,H1C), C30(H30A,H30B,H30C)
;