Asymmetric synthesis of spirooxindole–pyranoindole products via Friedel–Crafts alkylation/cyclization of the indole carbocyclic ring
Gao, Yuan; Wang, Xiaonan; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng; New Journal of Chemistry 44 (2020) 9788–9792; doi:10.1039/D0NJ00074D

data_7059595
_publ_section_title
;
 Asymmetric synthesis of spirooxindole--pyranoindole products via
 Friedel--Crafts alkylation/cyclization of the indole carbocyclic ring
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9788
_journal_page_last               9792
_journal_paper_doi               10.1039/D0NJ00074D
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H20 N4 O3'
_chemical_formula_sum            'C27 H20 N4 O3'
_chemical_formula_weight         448.48
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-18
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.2140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.5749(3)
_cell_length_b                   8.9564(2)
_cell_length_c                   12.5886(4)
_cell_measurement_reflns_used    9623
_cell_measurement_temperature    297.0
_cell_measurement_theta_max      27.960
_cell_measurement_theta_min      2.903
_cell_volume                     1170.83(6)
_computing_cell_refinement       'SAINT V8.40A (bu, 2016)'
_computing_data_reduction        'SAINT V8.40A (bu, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29710
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_extinction_coef       0.027(2)
_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   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.1917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                4116
_reflns_number_total             5819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj00074d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
 Adding full bibliography for 7059595.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.35 H1.74 N0.35 O0.26'
_cod_original_formula_weight         39.00
_cod_original_formula_moiety         'C2.348 H1.739 N0.348 O0.261'
_cod_original_formula_units_Z            23
_cod_original_cell_volume        1170.83(5)
_cod_database_code               7059595
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N14(H14A,H14B)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), N22(H22), C23(H23), C24(H24),
 C27(H27), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'