Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based bispirooxindoles through a three-component [3 + 2] cycloaddition.
Guo, Jiaomei; Zhao, Yang; Fang, Dongmei; Wang, Qilin; Bu, Zhanwei; Organic & biomolecular chemistry 16 (2018) 6025–6034; doi:10.1039/c8ob01493k

data_7156355
_publ_section_title
;
 Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based
 bispirooxindoles through a three-component [3 + 2] cycloaddition.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6025
_journal_page_last               6034
_journal_paper_doi               10.1039/c8ob01493k
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C34 H33 N3 O6'
_chemical_formula_sum            'C34 H33 N3 O6'
_chemical_formula_weight         579.63
_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     direct
_audit_creation_date             2017-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-18 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                86.119(6)
_cell_angle_beta                 84.314(6)
_cell_angle_gamma                65.589(7)
_cell_formula_units_Z            2
_cell_length_a                   11.2505(7)
_cell_length_b                   11.5713(10)
_cell_length_c                   13.0127(9)
_cell_measurement_reflns_used    2129
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1420
_cell_measurement_theta_min      3.8650
_cell_volume                     1534.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -41.00   28.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -90.0000 69

  2 omega  -12.00   23.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000  -90.0000 35

  3 omega  -15.00   19.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -180.0000 34

  4 omega  -39.00   13.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000 -120.0000 52

  5 omega  -48.00   45.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -77.0000   30.0000 93

  6 omega   -9.00   86.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   77.0000  150.0000 95

  7 omega   43.00   72.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  178.0000   90.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0446283000
_diffrn_orient_matrix_UB_12      0.0292497000
_diffrn_orient_matrix_UB_13      0.0425551000
_diffrn_orient_matrix_UB_21      0.0530687000
_diffrn_orient_matrix_UB_22      -0.0157881000
_diffrn_orient_matrix_UB_23      0.0312505000
_diffrn_orient_matrix_UB_31      0.0038901000
_diffrn_orient_matrix_UB_32      0.0585713000
_diffrn_orient_matrix_UB_33      -0.0146869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0652
_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       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12262
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.553
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.255
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0580P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3732
_reflns_number_total             6274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01493k2.cif
_cod_data_source_block           201712258
_cod_depositor_comments          'Adding full bibliography for 7156355.cif.'
_cod_database_code               7156355
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H56N2O3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.78
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'