Phosphine-catalysed denitrative rearomatising (3 + 2) annulation of α,β-ynones and 3-nitroindoles.
Dutta, Lona; Chattopadhyay, Anwita; Yadav, Nisha; Ramasastry, S. S. V.; Organic & biomolecular chemistry 21 (2023) 738–742; doi:10.1039/d2ob02180c

data_7159046
_publ_section_title
;
 Phosphine-catalysed denitrative rearomatising (3 + 2) annulation of
 &#x3b1;,&#x3b2;-ynones and 3-nitroindoles.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              738
_journal_page_last               742
_journal_paper_doi               10.1039/d2ob02180c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_chemical_name_systematic
(E)-4,4-dimethyl-1-(3-nitro-1H-indol-1-yl)-1-phenylpent-1-en-3-one
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-23 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                73.343(7)
_cell_angle_beta                 82.375(6)
_cell_angle_gamma                63.636(7)
_cell_formula_units_Z            2
_cell_length_a                   9.9977(7)
_cell_length_b                   10.0721(7)
_cell_length_c                   10.6301(8)
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      30.8920
_cell_measurement_theta_min      2.8070
_cell_volume                     918.83(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.843
_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    -67.00  23.00   0.30   30.00    --   29.89  54.00-150.00  300
  2  \w    -52.00 -25.00   0.30   30.00    --   29.89  54.00 -60.00   90
  3  \w    -64.00 117.80   0.30   30.00    --   29.89  54.00  90.00  606
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0473040000
_diffrn_orient_matrix_UB_12      0.0640618000
_diffrn_orient_matrix_UB_13      0.0248251000
_diffrn_orient_matrix_UB_21      -0.0530677000
_diffrn_orient_matrix_UB_22      -0.0310471000
_diffrn_orient_matrix_UB_23      0.0193543000
_diffrn_orient_matrix_UB_31      0.0348734000
_diffrn_orient_matrix_UB_32      -0.0392989000
_diffrn_orient_matrix_UB_33      0.0621302000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7049
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.74
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+0.1316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.2074
_reflns_number_gt                3249
_reflns_number_total             5725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob02180c2.cif
_cod_data_source_block           ld49p
_cod_depositor_comments          'Adding full bibliography for 7159046.cif.'
_cod_original_cell_volume        918.83(11)
_cod_database_code               7159046
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3A) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
3. Others
 Fixed Sof: C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5) H2A(0.5) H2B(0.5)
 H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5) H3C(0.5) C3A(0.5) H3AA(0.5) H3AB(0.5)
 H3AC(0.5) C2A(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5)
 H1AC(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC),
 C2A(H2AA,H2AB,H2AC), C1A(H1AA,H1AB,H1AC)
;
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.800