Rh(III)-Catalyzed [5+1] Annulation of 2-Alkenylanilides and 2-Alkenylphenols with Allenyl Acetates
Volla, Chandra; Singh, Anurag; Shukla, Rahul Kumar; Chemical Science  (2022) –; doi:10.1039/D1SC06097J

data_1566045
_publ_section_title
;
 Rh(III)-Catalyzed [5+1] Annulation of 2-Alkenylanilides and
 2-Alkenylphenols with Allenyl Acetates
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06097J
_journal_year                    2022
_chemical_formula_moiety         'C26 H22 F3 N O2 S'
_chemical_formula_sum            'C26 H22 F3 N O2 S'
_chemical_formula_weight         469.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4436(3)
_cell_length_b                   16.0587(6)
_cell_length_c                   38.2012(18)
_cell_measurement_reflns_used    8512
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.1620
_cell_measurement_theta_min      2.1120
_cell_volume                     4566.4(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_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   -110.00   1.50   0.50    8.00    --  -20.00 -72.00 -36.00  223
  2  \w    -68.50  17.00   0.50    8.00    --  -20.00 -72.00 108.00  171
  3  \w    -31.00  -1.00   0.50    8.00    --  -20.00   0.00-108.00   60
  4  \w    -59.00 -27.50   0.50    8.00    --  -20.00  72.00-180.00   63
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211015000
_diffrn_orient_matrix_UB_12      -0.0428634000
_diffrn_orient_matrix_UB_13      -0.0018445000
_diffrn_orient_matrix_UB_21      -0.0022562000
_diffrn_orient_matrix_UB_22      -0.0047501000
_diffrn_orient_matrix_UB_23      0.0184534000
_diffrn_orient_matrix_UB_31      -0.0928705000
_diffrn_orient_matrix_UB_32      -0.0096203000
_diffrn_orient_matrix_UB_33      -0.0008655000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.1177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            22474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.657
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1937
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.167
_refine_ls_abs_structure_details
;
 Flack x determined using 1568 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.57(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         8010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0792P)^2^+1.0088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5564
_reflns_number_total             8010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06097j2.cif
_cod_data_source_block           cmrv-as-415_mo
_cod_depositor_comments
;

2022-05-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C52 H44 F0.25 N2 O10 S2'
_cod_original_formula_weight         925.76
_cod_original_formula_moiety         '2(C26 H22 F3 N O2 S)'
_cod_original_formula_units_Z            4
_cod_database_code               1566045
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 93.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.11
_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.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C37(H37), C5(H5), C30(H30), C11(H11), C2(H2), C31(H31), C43(H43),
 C13(H13), C29(H29), C1(H1), C38(H38), C50(H50), C14(H14), C39(H39), C24(H24),
 C3(H3), C27(H27), C21(H21), C12(H12), C40(H40), C4(H4), C34(H34), C28(H28),
 C9(H9), C47(H47), C22(H22), C49(H49), C48(H48), C23(H23), C8(H8), C35(H35)
2.b Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C42(H42A,H42B,
 H42C)
;
_shelx_res_checksum              35788
_shelx_hkl_checksum              843
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.603