Ester directed orthogonal dual C-H activation and ortho aryl C-H alkenylation via distal weak coordination
Bakthadoss, Manickam; Reddy, Tadiparthi Thirupathi; Agarwal, Vishal; Sharada, Duddu Savaraiah; Chemical Communications  (2022) –; doi:10.1039/D1CC06097J

data_7129453
_publ_section_title
;
 Ester directed orthogonal dual C-H activation and ortho aryl C-H
 alkenylation via distal weak coordination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06097J
_journal_year                    2022
_chemical_formula_moiety         'C22 H20 F2 O4'
_chemical_formula_sum            'C22 H18 F2 O4'
_chemical_formula_weight         384.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2021-09-19 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.067(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7331(11)
_cell_length_b                   20.6428(19)
_cell_length_c                   12.1338(15)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1133
_cell_measurement_theta_min      3.9406
_cell_volume                     1932.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details
;
  1 omega   16.00   50.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  -90.0000 34

  2 omega  -47.00  -21.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  -90.0000 26

  3 omega   17.00   55.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -90.0000 38

  4 omega  -59.00  -33.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  178.0000   30.0000 26

  5 omega  -18.00    9.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -90.0000 27

  6 omega  -72.00    1.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  -30.0000 73

  7 omega  -36.00   13.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000 -120.0000 49

  8 omega  -44.00  -16.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -60.0000 28

  9 omega   33.00   90.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585 -178.0000  -60.0000 57
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0254322000
_diffrn_orient_matrix_UB_12      -0.0148738000
_diffrn_orient_matrix_UB_13      -0.0490846000
_diffrn_orient_matrix_UB_21      0.0132139000
_diffrn_orient_matrix_UB_22      0.0309450000
_diffrn_orient_matrix_UB_23      -0.0232979000
_diffrn_orient_matrix_UB_31      0.0873614000
_diffrn_orient_matrix_UB_32      -0.0003387000
_diffrn_orient_matrix_UB_33      0.0220742000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12321
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         4.38
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0940
_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^)+(0.1030P)^2^+2.2075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2798
_reflns_number_gt                2502
_reflns_number_total             4469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc06097j2.cif
_cod_data_source_block           mb-ttr-219-g
_cod_database_code               7129453
_chemical_oxdiff_formula         'C10 H20 O4 Cl4 F1'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 295K, 0.75 0.32 0.12'
_reflns_odcompleteness_completeness 99.09
_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:
 C11(H11A,H11B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C16(H16), C15(H15), C3(H3), C5(H5), C2(H2), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'