Brønsted acid-promoted synthesis of highly functionalized tetrahydrocarbazoles from diethyl (<i>E</i>)-5-diazo-4-oxohex-2-enedioate.
Arunkumar, Vemula; Balamurugan, Rengarajan; Organic & biomolecular chemistry 22 (2024) 9214–9218; doi:10.1039/d4ob00992d

data_7160130
_publ_section_title
;
 Br&#xf8;nsted acid-promoted synthesis of highly functionalized
 tetrahydrocarbazoles from diethyl
 (<i>E</i>)-5-diazo-4-oxohex-2-enedioate.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9214
_journal_page_last               9218
_journal_paper_doi               10.1039/d4ob00992d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H21 N O5'
_chemical_formula_sum            'C19 H21 N O5'
_chemical_formula_weight         343.38
_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_Int_Tables_number      14
_audit_creation_date             2021-07-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.960(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4646(7)
_cell_length_b                   21.096(2)
_cell_length_c                   10.1483(10)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.30
_cell_volume                     1742.3(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      288.0
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49348
_diffrn_reflns_theta_full        27.5551
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0999 before and 0.0712 after correction. The Ratio of minimum to maximum transmission is 0.9084. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3089
_exptl_crystal_description       plate
_exptl_crystal_F_000             728.4229
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.6833
_refine_diff_density_min         -0.4759
_refine_diff_density_rms         0.1334
_refine_ls_d_res_high            0.7682
_refine_ls_d_res_low             10.5481
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0575
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1195P)^2^+0.2869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1976
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2823
_reflns_number_total             4013
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00992d2.cif
_cod_data_source_block           RB001A_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160128--7160130.cif.'
_cod_database_code               7160130
_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:
 C13(H13), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C15(H15a,H15b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1)
2.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C16(H16a,H16b,H16c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'