Organocatalytic Asymmetric Michael-Michael Cascade for the Construction of Highly Functionalized N-Fused Piperidinoindoline Derivatives.
Zhao, Yong-Long; Wang, Yao; Cao, Jian; Liang, Yong-Min; Xu, Peng-Fei; Organic letters 16 (2014) 2438–2441; doi:10.1021/ol5008185

data_1514345
_publ_section_title
;
 Organocatalytic Asymmetric Michael-Michael Cascade for the Construction
 of Highly Functionalized N-Fused Piperidinoindoline Derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2438
_journal_page_last               2441
_journal_paper_doi               10.1021/ol5008185
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration none
_chemical_formula_moiety         'C24 H23 Br N2 O7'
_chemical_formula_sum            'C24 H23 Br N2 O7'
_chemical_formula_weight         531.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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Olex2 1.2
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3460
_cell_measurement_theta_min      3.5300
_cell_volume                     2370.8(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0484260000
_diffrn_orient_matrix_UB_12      -0.0183308000
_diffrn_orient_matrix_UB_13      0.0271459000
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_diffrn_orient_matrix_UB_23      0.0122321000
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_diffrn_orient_matrix_UB_32      0.0313897000
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_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_number            6631
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.984
_diffrn_reflns_theta_min         3.065
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
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_refine_diff_density_max         0.445
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
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 Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
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_refine_ls_abs_structure_Flack   -0.016(13)
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0186P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5008185_si_002.cif
_cod_data_source_block           zhaoyl1218
_cod_depositor_comments          'Adding full bibliography for 1514345.cif.'
_cod_database_code               1514345
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.64
_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:
 C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
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