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_7232594
_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         'C37 H27 N3 O3'
_chemical_formula_sum            'C37 H27 N3 O3'
_chemical_formula_weight         561.61
_chemical_name_systematic
'1'S * ,2'S * ,3S * ,10b'S * ) - 1''-phenyl - 2'-( pyridin-2-yl )- 6',10b'-dihydro-2H,2'H,5'H-dispiro [acenaphthylene-1,3'-pyrrolo[2,1-a]isoquinoline-1',3''-pyrrolidine]-2,2'',5''-trione'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-10
_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.    2019-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.888(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7916(5)
_cell_length_b                   9.7185(4)
_cell_length_c                   24.5997(10)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.3950
_cell_measurement_theta_min      2.6530
_cell_volume                     2817.5(2)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            39113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97807
_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    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0388P)^2^+1.1948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4875
_reflns_number_total             6140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra09884k2.cif
_cod_data_source_block           3007
_cod_database_code               7232594
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H37A)=Sof(H35A)=Sof(N3B)=Sof(C34B)=Sof(H34B)=1-FVAR(1)
 Sof(N3A)=Sof(C34A)=Sof(H34A)=Sof(H37)=Sof(H35)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C21(H21), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C34A(H34A), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C16(H16),
 C17(H17), C18(H18), C19(H19), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C36(H36), C37(H37), C37(H37A), C35(H35), C35(H35A), C34B(H34B)
;
_shelx_res_checksum              79919
_olex2_submission_special_instructions 'No special instructions were received'