Copper(i) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides.
Muthusamy, Sengodagounder; Kumar, Singaravelan Ganesh; Organic & biomolecular chemistry 14 (2016) 2228–2240; doi:10.1039/c5ob02322j

data_7154899
_publ_section_title
;
 Copper(i) catalyzed diastereoselective multicomponent synthesis of
 spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides
 via azomethine ylides.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2228
_journal_page_last               2240
_journal_paper_doi               10.1039/c5ob02322j
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         '0.5(C32 H24 Br N3 O3)'
_chemical_formula_sum            'C32 H24 Br N3 O3'
_chemical_formula_weight         578.44
_chemical_melting_point          431
_chemical_name_systematic        spiroindolopyrrole
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-14
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2015-10-20 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.744(6)
_cell_angle_beta                 93.929(5)
_cell_angle_gamma                90.612(7)
_cell_formula_units_Z            2
_cell_length_a                   9.6198(8)
_cell_length_b                   11.1689(9)
_cell_length_c                   13.4682(6)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    251(18)
_cell_measurement_theta_max      29.2205
_cell_measurement_theta_min      2.5830
_cell_volume                     1320.30(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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_computing_molecular_graphics
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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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      251(18)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -18.00   25.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -30.0000 43

  2 omega  -20.00   15.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -180.0000 35

  3 omega  -88.00  -60.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -179.0000 -150.0000 28

  4 omega  -46.00   76.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -       18.9803    0.0000    0.0000 122

  5 omega  -90.00  -47.00   1.0000   13.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000   60.0000 43
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0501839000
_diffrn_orient_matrix_UB_12      0.0482875000
_diffrn_orient_matrix_UB_13      0.0072354000
_diffrn_orient_matrix_UB_21      -0.0528061000
_diffrn_orient_matrix_UB_22      -0.0444515000
_diffrn_orient_matrix_UB_23      0.0006154000
_diffrn_orient_matrix_UB_31      0.0128416000
_diffrn_orient_matrix_UB_32      0.0226792000
_diffrn_orient_matrix_UB_33      0.0572590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7527
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       diamond
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1620
_reflns_number_gt                3260
_reflns_number_total             4868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02322j2.cif
_cod_data_source_block           spiroindolopyrrole
_cod_depositor_comments
'Adding full bibliography for 7154899--7154900.cif.'
_cod_original_cell_volume        1320.30(16)
_cod_database_code               7154899
_chemical_oxdiff_formula         'C32 H24 Br1 N3 O3'
_chemical_oxdiff_usercomment     '264 K, COLORLESS, PLATE'
_reflns_odcompleteness_completeness 81.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32