Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivatives via multicomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinolinium N-ylides
Boudriga, Sarra; Haddad, Saoussen; Askri, Moheddine; Soldera, Armand; Knorr, Michael; Strohmann, Carsten; Golz, Christopher; RSC Advances 9 (2019) 11082–; doi:10.1039/C8RA09884K

data_7232592
_publ_section_title
;
 Highly diastereoselective construction of novel
 dispiropyrrolo[2,1-a]isoquinoline derivatives via multicomponent
 1,3-dipolar cycloaddition of cyclic diketones-based
 tetrahydroisoquinolinium N-ylides
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              11082
_journal_paper_doi               10.1039/C8RA09884K
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C34 H27 N3 O3'
_chemical_formula_sum            'C34 H27 N3 O3'
_chemical_formula_weight         525.58
_chemical_name_systematic
(1'R*,2'R*,3R*,10b'R*)-1',1''-diphenyl-1',5',6',10b'-tetrahydrodispiro[indoline-3,3'-pyrrolo[2,1-a]isoquinoline-2',3''-pyrrolidine]-2,2'',5''-trione
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-17
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2017-11-14 deposited with the CCDC.    2019-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                65.084(5)
_cell_angle_beta                 80.892(4)
_cell_angle_gamma                79.404(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8139(3)
_cell_length_b                   12.9798(6)
_cell_length_c                   14.2280(7)
_cell_measurement_reflns_used    11170
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.0420
_cell_measurement_theta_min      2.7560
_cell_volume                     1281.12(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -47.00   16.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4645  -57.0000 -120.0000 63

  2 omega   19.00   79.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4645 -131.0000  -79.5535 60

  3 omega  -14.00   59.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4645  -99.0000  -16.0000 73

  4 omega  -91.00    5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -38.0000   90.0000 96

  5 omega  -25.00   49.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708   57.0000  150.0000 74

  6 omega   -8.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708   57.0000   30.0000 58

  7 omega  -88.00    3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -57.0000    0.0000 91

  8 omega  -25.00   23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -99.0000  150.0000 48

  9 omega  -87.00    3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -57.0000 -120.0000 90

 10 omega  -75.00    1.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  123.0000   40.9583 76

 11 omega  -55.00   43.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4645  -38.0000  -60.0000 98

 12 omega   -4.00   86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4645   57.0000   30.0000 90

 13 omega  -72.00    9.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  118.0000  133.8350 81

 14 omega  -89.00   11.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -77.0000 -120.0000 100

 15 omega  -25.00   23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -99.0000  -90.0000 48

 16 omega  -25.00   23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708  -99.0000   90.0000 48

 17 omega  -40.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8708   57.0000   90.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0026865000
_diffrn_orient_matrix_UB_12      -0.0153449000
_diffrn_orient_matrix_UB_13      -0.0420054000
_diffrn_orient_matrix_UB_21      0.0595128000
_diffrn_orient_matrix_UB_22      0.0392287000
_diffrn_orient_matrix_UB_23      -0.0310299000
_diffrn_orient_matrix_UB_31      0.0710630000
_diffrn_orient_matrix_UB_32      -0.0438123000
_diffrn_orient_matrix_UB_33      0.0178681000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33514
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         2.663
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0485P)^2^+0.4393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4514
_reflns_number_total             5562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra09884k2.cif
_cod_data_source_block           3055
_cod_database_code               7232592
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         'C34 H27 N3 O3'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N7-H7
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C25(H25), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C32(H32A,H32B), C36(H36A,H36B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C22(H22), C24(H24),
 C28(H28), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C37(H37), C38(H38),
  C39(H39), C40(H40)
;
_shelx_res_checksum              59312