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_7156992
_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         'C25 H19 Br2 N3 O5'
_chemical_formula_sum            'C25 H19 Br2 N3 O5'
_chemical_formula_weight         601.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-26 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.00(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2334(8)
_cell_length_b                   9.4327(6)
_cell_length_c                   23.5205(18)
_cell_measurement_reflns_used    29728
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.733
_cell_volume                     2490.7(3)
_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      296.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_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  0.1300
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29728
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.733
_exptl_absorpt_coefficient_mu    3.296
_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
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0778P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2699
_reflns_number_total             4386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01249d2.cif
_cod_data_source_block           4out
_cod_depositor_comments
'Adding full bibliography for 7156991--7156992.cif.'
_cod_database_code               7156992
_shelx_shelxl_version_number     2014/7
_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 Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C18(H18a,H18b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C21(H21),
 C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c)
;
_olex2_submission_special_instructions 'No special instructions were received'