Catalytic Asymmetric Dearomative [3 + 2] Cycloaddition of Electron-Deficient Indoles with All-Carbon 1,3-Dipoles.
Sun, Meng; Zhu, Zi-Qi; Gu, Ling; Wan, Xiao; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 83 (2018) 2341–2348; doi:10.1021/acs.joc.7b03259

data_4033489
_publ_section_title
;
 Catalytic Asymmetric Dearomative [3 + 2] Cycloaddition of
 Electron-Deficient Indoles with All-Carbon 1,3-Dipoles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2341
_journal_page_last               2348
_journal_paper_doi               10.1021/acs.joc.7b03259
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H16 N4 O3'
_chemical_formula_sum            'C22 H16 N4 O3'
_chemical_formula_weight         384.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.557(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8423(7)
_cell_length_b                   6.5103(5)
_cell_length_c                   19.3939(16)
_cell_measurement_reflns_used    939
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      69.760
_cell_measurement_theta_min      5.98
_cell_volume                     1868.1(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19671
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.207
_diffrn_reflns_theta_min         2.987
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1462 before and 0.0816 after correction. The Ratio of minimum to maximum transmission is 0.7341. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_extinction_coef       0.0027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0211P)^2^+1.0747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                6176
_reflns_number_total             6713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03259_si_002.cif
_cod_data_source_block           cu_d8v17202_0m
_cod_depositor_comments          'Adding full bibliography for 4033489.cif.'
_cod_database_code               4033489
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C1A(H1A), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C8A(H8A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB)
;
_shelx_res_checksum              8465
_shelx_hkl_checksum              34455
_olex2_submission_special_instructions 'No special instructions were received'