Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)-N(1')-bisindoles and C(3)-N(1')-diindolylmethane.
Hajra, Saumen; Maity, Subrata; Roy, Sayan; Das, Dhiraj; Organic & biomolecular chemistry 17 (2019) 7747–7759; doi:10.1039/c9ob01249d

data_7156991
_publ_section_title
;
 Controlling the regioselectivity of the ring opening of
 spiro-epoxyoxindoles for efficient synthesis of C(3)-N(1')-bisindoles and
 C(3)-N(1')-diindolylmethane.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7747
_journal_page_last               7759
_journal_paper_doi               10.1039/c9ob01249d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C31 H33 N3 O4'
_chemical_formula_sum            'C31 H33 N3 O4'
_chemical_formula_weight         511.60
_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     iterative
_audit_creation_date             2018-10-26
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2018-12-26 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                111.235(17)
_cell_angle_beta                 91.111(16)
_cell_angle_gamma                102.013(16)
_cell_formula_units_Z            2
_cell_length_a                   9.899(2)
_cell_length_b                   11.547(3)
_cell_length_c                   13.186(3)
_cell_measurement_reflns_used    15844
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      2.72
_cell_volume                     1366.7(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1624
_diffrn_reflns_av_unetI/netI     0.1749
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15844
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.727
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
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_refine_diff_density_max         0.148
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         4803
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.0645
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             4803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01249d2.cif
_cod_data_source_block           sm_out
_cod_depositor_comments
'Adding full bibliography for 7156991--7156992.cif.'
_cod_original_cell_volume        1366.8(6)
_cod_database_code               7156991
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C16(H16a,H16b), C25(H25a,H25b), C26(H26a,H26b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), N3(H3)
2.c Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'