Advanced palladium free approach to the synthesis of substituted alkene oxindoles via aluminum-promoted Knoevenagel reaction
Novikova, Daria S.; Grigoreva, Tatyana A.; Zolotarev, Andrey A.; Garabadzhiu, Alexander V.; Tribulovich, Vyacheslav G.; RSC Advances 8 (2018) 34543–; doi:10.1039/C8RA07576J

data_7231627
_publ_section_title
;
 Advanced palladium free approach to the synthesis of substituted alkene
 oxindoles via aluminum-promoted Knoevenagel reaction
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              34543
_journal_paper_doi               10.1039/C8RA07576J
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C30 H22 Cl0.76 N O3'
_chemical_formula_sum            'C30 H22 Cl0.75 N O3'
_chemical_formula_weight         471.25
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-14 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                69.018(7)
_cell_angle_beta                 85.368(6)
_cell_angle_gamma                85.951(6)
_cell_formula_units_Z            2
_cell_length_a                   10.2260(7)
_cell_length_b                   10.6156(8)
_cell_length_c                   11.7663(8)
_cell_measurement_reflns_used    5824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7050
_cell_measurement_theta_min      2.9250
_cell_volume                     1187.51(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -36.00   44.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000  120.0000 80

  2 omega  -84.00  -43.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  131.0000  -45.0000 41

  3 omega  -87.00  -17.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  139.0000  129.0000 70

  4 omega  -87.00   -3.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -57.0000 -120.0000 84

  5 omega  -90.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -19.0000  -60.0000 109

  6 omega  -36.00   45.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   38.0000  -60.0000 81

  7 omega  -61.00   48.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   19.0000   60.0000 109

  8 omega  -63.00   -4.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000   60.0000 59

  9 omega  -79.00    7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000  150.0000 86

 10 omega   -6.00   44.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000    0.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0023686000
_diffrn_orient_matrix_UB_12      0.0620535000
_diffrn_orient_matrix_UB_13      0.0102351000
_diffrn_orient_matrix_UB_21      0.0057722000
_diffrn_orient_matrix_UB_22      0.0355568000
_diffrn_orient_matrix_UB_23      -0.0638378000
_diffrn_orient_matrix_UB_31      -0.0693798000
_diffrn_orient_matrix_UB_32      0.0040613000
_diffrn_orient_matrix_UB_33      -0.0017921000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17805
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.804
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0494P)^2^+0.8321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4448
_reflns_number_total             5168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07576j2.cif
_cod_data_source_block           0nds11
_cod_original_cell_volume        1187.51(15)
_cod_database_code               7231627
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C30 H22 Cl0.75 N O3'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
  C28(H28)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'