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_7160129
_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         'C28 H26 N2 O4'
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-27
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-06-28 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                109.715(9)
_cell_angle_beta                 97.202(7)
_cell_angle_gamma                106.377(7)
_cell_formula_units_Z            2
_cell_length_a                   7.8862(5)
_cell_length_b                   12.8660(12)
_cell_length_c                   12.9041(13)
_cell_measurement_reflns_used    4361
_cell_measurement_temperature    295.83
_cell_measurement_theta_max      21.6250
_cell_measurement_theta_min      2.7150
_cell_volume                     1146.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      295.83
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -43.00  54.00   0.50    4.00    --  -15.60  61.00   0.00  194
  2  \w    -15.00  89.00   0.50    4.00    --   16.22  77.00 -60.00  208
  3  \w    -15.00  89.00   0.50    4.00    --   16.22  77.00-150.00  208
  4  \w    -10.00  90.00   0.50    4.00    --   16.22  30.00-180.00  200
  5  \w    -41.00  58.00   0.50    4.00    --  -15.60  30.00 -60.00  198
  6  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00-120.00  116
  7  \w     28.00  91.00   0.50    4.00    --   16.22-158.00 -95.00  126
  8  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00   0.00  116
  9  \w      5.00  66.00   0.50    4.00    --   16.22-118.00  58.00  122
 10  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00 120.00  116
 11  \w    -37.00  53.00   0.50    4.00    --   16.22 -94.00  90.00  180
 12  \w    -37.00  15.00   0.50    4.00    --  -15.60 -94.00  30.00  104
 13  \w    -54.00  41.00   0.50    4.00    --   16.22 -45.00  90.00  190
 14  \w    -10.00  90.00   0.50    4.00    --   16.22  30.00  60.00  200
 15  \w    -66.00  -5.00   0.50    4.00    --  -15.60 118.00 144.00  122
 16  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00 -90.00  120
 17  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00-150.00  120
 18  \w    -40.00  55.00   0.50    4.00    --  -15.60  45.00-180.00  190
 19  \w    -90.00 -28.00   0.50    4.00    --  -15.60 158.00 -61.00  124
 20  \w    -89.00   9.00   0.50    4.00    --  -15.60 -30.00-150.00  196
 21  \w    -85.00  12.00   0.50    4.00    --  -15.60 -61.00  60.00  194
 22  \w    -89.00   9.00   0.50    4.00    --  -15.60 -30.00 120.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221715000
_diffrn_orient_matrix_UB_12      -0.0087570000
_diffrn_orient_matrix_UB_13      -0.0580279000
_diffrn_orient_matrix_UB_21      0.0435740000
_diffrn_orient_matrix_UB_22      0.0611495000
_diffrn_orient_matrix_UB_23      0.0148466000
_diffrn_orient_matrix_UB_31      0.0833955000
_diffrn_orient_matrix_UB_32      -0.0091472000
_diffrn_orient_matrix_UB_33      -0.0061458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3342
_diffrn_reflns_av_unetI/netI     0.2730
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.712
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_min         1.943
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.3194
_refine_ls_R_factor_gt           0.1744
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3970
_refine_ls_wR_factor_ref         0.5818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1155
_reflns_number_total             3915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00992d2.cif
_cod_data_source_block           rb54
_cod_depositor_comments
'Adding full bibliography for 7160128--7160130.cif.'
_cod_original_cell_volume        1146.77(19)
_cod_database_code               7160129
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C25(H25A,H25B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C2(H2), C5(H5), C19(H19), C16(H16), C3(H3), C18(H18),
 C4(H4), C17(H17)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              5737
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.364
_oxdiff_exptl_absorpt_empirical_full_min 0.192