The solvent-controlled Rh(iii)-catalyzed switchable [4+2] annulation of 2-arylIndoles with iodonium ylides
Nunewar, Saiprasad; Kumar, Sanjeev; Priyanka, Pendam; Girase, Pradeep; Kanchupalli, Vinaykumar; Chemical Communications  (2022) –; doi:10.1039/D2CC01386J

data_7130046
_publ_section_title
;
 The solvent-controlled Rh(iii)-catalyzed switchable [4+2] annulation of
 2-arylIndoles with iodonium ylides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01386J
_journal_year                    2022
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bd823
_audit_creation_date             2021-10-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-03-07 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6240(5)
_cell_length_b                   9.8728(3)
_cell_length_c                   19.5796(6)
_cell_measurement_reflns_used    9439
_cell_measurement_temperature    293(14)
_cell_measurement_theta_max      26.6330
_cell_measurement_theta_min      2.1010
_cell_volume                     3213.51(17)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9680
_diffrn_measured_fraction_theta_max 0.9680
_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    -57.00 -17.00   0.50   38.14    --   16.22 -79.00  57.00   80
  2  \w    -37.00  16.00   0.50   38.14    --  -14.97 -94.00  30.00  106
  3  \w     31.00  65.00   0.50   38.14    --   16.22-125.00  60.00   68
  4  \w    -17.00  57.00   0.50   38.14    --   16.22-102.00 -32.00  148
  5  \w    -64.00 -11.00   0.50   38.14    --  -14.97 125.00   0.00  106
  6  \w     -6.00  67.00   0.50   38.14    --   16.22  45.00 -90.00  146
  7  \w    -31.00  -6.00   0.50   38.14    --   16.22 -48.00-168.00   50
  8  \w    -33.00  16.00   0.50   38.14    --  -14.97 -94.00-180.00   98
  9  \w    -37.00  26.00   0.50   38.14    --   16.22 -94.00 -90.00  126
 10  \w    -67.00 -22.00   0.50   38.14    --  -14.97 125.00-120.00   90
;
_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      0.0389499000
_diffrn_orient_matrix_UB_12      -0.0015047000
_diffrn_orient_matrix_UB_13      -0.0147756000
_diffrn_orient_matrix_UB_21      0.0139290000
_diffrn_orient_matrix_UB_22      -0.0404236000
_diffrn_orient_matrix_UB_23      0.0275169000
_diffrn_orient_matrix_UB_31      -0.0104775000
_diffrn_orient_matrix_UB_32      -0.0593906000
_diffrn_orient_matrix_UB_33      -0.0183321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20142
_diffrn_reflns_theta_full        26.9910
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30163
_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 yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2955
_exptl_crystal_description       block
_exptl_crystal_F_000             1328.5591
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2144
_refine_diff_density_min         -0.2475
_refine_diff_density_rms         0.0602
_refine_ls_d_res_high            0.7830
_refine_ls_d_res_low             9.7898
_refine_ls_goodness_of_fit_ref   1.0241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0241
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0673P)^2^+0.0485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2353
_reflns_number_total             3391
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2cc01386j2.cif
_cod_data_source_block           EXTER33
_cod_database_code               7130046
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.68
_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:
 C17(H17a,H17b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C13(H13), C10(H10), C2(H2), C12(H12), C11(H11), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c)
;
_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 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.586