Palladium-catalyzed remote <i>meta</i>-C-H olefination of cinnamates.
Bakthadoss, Manickam; Hussain, Mir Ashiq; Reddy, Tadiparthi Thirupathi; Chemical communications (Cambridge, England) 59 (2023) 5249–5252; doi:10.1039/d3cc00289f

data_7131501
_publ_section_title
;
 Palladium-catalyzed remote <i>meta</i>-C-H olefination of cinnamates.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5249
_journal_page_last               5252
_journal_paper_doi               10.1039/d3cc00289f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H18 Br N O6'
_chemical_formula_sum            'C23 H18 Br N O6'
_chemical_formula_weight         484.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-01-10 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.6790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.99040(10)
_cell_length_b                   22.6800(2)
_cell_length_c                   11.91330(10)
_cell_measurement_reflns_used    32118
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.0970
_cell_measurement_theta_min      3.6940
_cell_volume                     2148.36(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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     44.00 127.00   0.50    0.20    --   96.67-145.00 -60.00  166
  2  \w     44.00 127.00   0.50    0.20    --   96.67-145.00   0.00  166
  3  \w     22.00 106.00   0.50    0.20    --   96.67 -96.00  90.00  168
  4  \w     30.00 109.00   0.50    0.20    --   96.67-117.00  90.00  158
  5  \w     18.00  79.00   0.50    0.20    --   40.33-104.00 150.00  122
  6  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00 120.00  154
  7  \w     41.00  99.00   0.50    0.20    --   40.33-138.00 -30.00  116
  8  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00 120.00   78
  9  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00 -30.00  108
 10  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00 -90.00  154
 11  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-180.00   78
 12  \w     41.00  99.00   0.50    0.20    --   40.33-138.00-180.00  116
 13  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00 -60.00  108
 14  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00-150.00   54
 15  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -60.00   54
 16  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -30.00   54
 17  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00   0.00   54
 18  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  60.00   54
 19  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 20  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00 150.00   78
 21  \w    -26.00  43.00   0.50    0.20    --   40.33 -38.00  94.00  138
 22  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00 -30.00  122
 23  \w     82.00 167.00   0.50    0.20    --   96.67  25.00   0.00  170
 24  \w     75.00 164.00   0.50    0.20    --   96.67  59.00 -30.00  178
 25  \w     75.00 164.00   0.50    0.20    --   96.67  59.00   0.00  178
 26  \w     75.00 164.00   0.50    0.20    --   96.67  59.00 -90.00  178
 27  \w     75.00 164.00   0.50    0.20    --   96.67  59.00  30.00  178
 28  \w     78.00 163.00   0.50    0.20    --   96.67  50.00  60.00  170
 29  \w     75.00 164.00   0.50    0.20    --   96.67  59.00  90.00  178
 30  \w     70.00 165.00   0.50    0.20    --   96.67  77.00 120.00  190
 31  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 150.00  190
 32  \w     70.00 165.00   0.50    0.20    --   96.67  77.00 150.00  190
 33  \w     78.00 163.00   0.50    0.20    --   96.67  50.00 -60.00  170
 34  \w     81.00 163.00   0.50    0.20    --   96.67  38.00-111.00  164
 35  \w     25.00 107.00   0.50    0.20    --   40.33  38.00-111.00  164
 36  \w     99.00 164.00   0.50    0.20    --   96.67 117.00-120.00  130
 37  \w    105.00 170.00   0.50    0.20    --   96.67  96.00-180.00  130
 38  \w    105.00 170.00   0.50    0.20    --   96.67  96.00-150.00  130
 39  \w     99.00 164.00   0.50    0.20    --   96.67 117.00 150.00  130
 40  \w    -43.00  26.00   0.50    0.20    --  -40.33  38.00-111.00  138
 41  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00-180.00  118
 42  \w    -31.00  30.00   0.50    0.20    --  -40.33  25.00 -30.00  122
 43  \w    -43.00  26.00   0.50    0.20    --  -40.33  38.00 -30.00  138
 44  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  30.00   64
 45  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 120.00   64
 46  \w    -78.00   4.00   0.50    0.20    --  -40.33 104.00  30.00  164
 47  \w    -43.00 -16.00   0.50    0.20    --  -82.50  38.00-111.00   54
 48  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  30.00  192
 49  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  90.00  192
 50  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -60.00  192
 51  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  60.00  192
 52  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -30.00  192
 53  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -90.00  192
 54  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-120.00  192
 55  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-150.00  192
 56  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-180.00  192
 57  \w   -110.00 -26.00   0.50    0.20    --  -40.33 -25.00 -60.00  168
 58  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00   0.00  192
 59  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 150.00  192
 60  \w   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00  94.00  162
 61  \w   -150.00 -69.00   0.50    0.20    --  -82.50 -33.00 150.00  162
 62  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  90.00  192
 63  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  30.00  192
 64  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  60.00  192
 65  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 120.00  192
 66  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00   0.00  192
 67  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -60.00  192
 68  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-180.00  192
 69  \w   -150.00 -58.00   0.50    0.20    --  -82.50 -68.00-150.00  184
 70  \w   -150.00 -58.00   0.50    0.20    --  -82.50 -68.00-120.00  184
 71  \w   -149.00 -67.00   0.50    0.20    --  -82.50 -38.00  94.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1383
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            41106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         3.898
_exptl_absorpt_coefficient_mu    2.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0550P)^2^+1.4562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3853
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00289f2.cif
_cod_data_source_block           1_100k_11
_cod_depositor_comments
'Adding full bibliography for 7131501--7131502.cif.'
_cod_database_code               7131501
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.589
_shelx_estimated_absorpt_t_min   0.384
_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C3(H3), C11(H11), C6(H6), C8(H8), C17(H17), C19(H19), C5(H5),
 C7(H7), C18(H18)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              72031
_shelx_hkl_checksum              95860
_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
;