Cp*Ir(III) and Cp*Rh(III)-catalyzed annulation of salicylaldehydes with fluorinated vinyl tosylates.
Zhao, Shuwen; Cai, Xiaojia; Lu, Yuying; Hu, Jinhui; Xiong, Zhuang; Jin, Jingwei; Li, Yin; Wang, Honggen; Wu, Jia-Qiang; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc02194c

data_7130367
_publ_section_title
;
 Cp*Ir(III) and Cp*Rh(III)-catalyzed annulation of salicylaldehydes with
 fluorinated vinyl tosylates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc02194c
_journal_year                    2022
_chemical_formula_moiety         'C11 H6 Cl F3 O3'
_chemical_formula_sum            'C11 H6 Cl F3 O3'
_chemical_formula_weight         278.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-06-07 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.625(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.72550(10)
_cell_length_b                   22.4433(7)
_cell_length_c                   10.8444(3)
_cell_measurement_reflns_used    4377
_cell_measurement_temperature    297.56(10)
_cell_measurement_theta_max      75.1880
_cell_measurement_theta_min      3.9350
_cell_volume                     1146.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.56(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_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     94.00 167.00   0.50    0.88    --  108.86  57.00 -90.00  146
  2  \w    145.00 177.00   0.50    0.88    --  108.86 125.00-150.00   64
  3  \w     96.00 123.00   0.50    0.88    --  108.86 125.00-150.00   54
  4  \w    105.00 130.00   0.50    0.88    --  108.86 140.00  -9.00   50
  5  \w    -62.00 -37.00   0.50    0.88    --  -91.75 140.00  -9.00   50
  6  \w    -73.00 -25.00   0.50    0.22    --  -48.55 140.00  -9.00   96
  7  \w   -115.00 -27.00   0.50    0.22    --  -48.55 -77.00   0.00  176
  8  \w   -163.00 -77.00   0.50    0.88    --  -91.75-130.00 104.00  172
  9  \w   -120.00 -95.00   0.50    0.22    --  -48.55-130.00 104.00   50
 10  \w   -116.00 -91.00   0.50    0.22    --  -48.55-140.00 -69.00   50
 11  \w   -163.00 -91.00   0.50    0.88    --  -91.75 -57.00 -60.00  144
 12  \w    -24.00  24.00   0.50    0.22    --  -48.55  19.00 -60.00   96
 13  \w    -45.00 -20.00   0.50    0.88    --  -91.75  57.00-150.00   50
 14  \w   -104.00 -75.00   0.50    0.88    --  -91.75  77.00   0.00   58
 15  \w    -61.00 -20.00   0.50    0.88    --  -91.75  57.00 -30.00   82
 16  \w    -53.00 -22.00   0.50    0.88    --  -91.75  57.00   0.00   62
 17  \w     38.00  66.00   0.50    0.88    --  108.86 -57.00  60.00   56
 18  \w     63.00  95.00   0.50    0.88    --  108.86 -77.00  90.00   64
 19  \w     40.00  65.00   0.50    0.88    --  108.86 -57.00 150.00   50
 20  \w     47.00  75.00   0.50    0.88    --  108.86-130.00 104.00   56
 21  \w     89.00 114.00   0.50    0.88    --  108.86-130.00 104.00   50
 22  \w     57.00  82.00   0.50    0.22    --   48.55-130.00 104.00   50
 23  \w     57.00 104.00   0.50    0.22    --   48.55-140.00 -69.00   94
 24  \w     94.00 119.00   0.50    0.88    --  108.86-140.00 -69.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137765000
_diffrn_orient_matrix_UB_12      -0.0524852000
_diffrn_orient_matrix_UB_13      -0.0918128000
_diffrn_orient_matrix_UB_21      0.0003276000
_diffrn_orient_matrix_UB_22      0.0441668000
_diffrn_orient_matrix_UB_23      -0.1087404000
_diffrn_orient_matrix_UB_31      0.3268239000
_diffrn_orient_matrix_UB_32      -0.0022551000
_diffrn_orient_matrix_UB_33      0.0076990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.402
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0996P)^2^+0.4930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1861
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02194c2.cif
_cod_data_source_block           exp_3268_auto
_cod_database_code               7130367
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F15B(0.5) F15A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C7(H7)
;
_shelx_res_checksum              46185
_shelx_hkl_checksum              94820
_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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.545