Distal <i>meta</i>-C-H functionalization of α-substituted cinnamates.
Bakthadoss, Manickam; Reddy, Tadiparthi Thirupathi; Chemical science 14 (2023) 5880–5886; doi:10.1039/d2sc06206b

data_1568529
_publ_section_title
;
 Distal <i>meta</i>-C-H functionalization of &#x3b1;-substituted
 cinnamates.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              5880
_journal_page_last               5886
_journal_paper_doi               10.1039/d2sc06206b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H21 N O5'
_chemical_formula_sum            'C23 H21 N O5'
_chemical_formula_weight         391.41
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-22
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.515(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7248(8)
_cell_length_b                   23.0566(19)
_cell_length_c                   12.1391(13)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1164
_cell_measurement_theta_min      3.5275
_cell_volume                     2102.2(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(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details
;
  1 omega  -39.00   13.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -77.0000 -150.0000 52

  2 omega  -92.00  -37.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000 -120.0000 55

  3 omega  -93.00  -55.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000  -30.0000 38

  4 omega  -24.00   14.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   30.0000 38

  5 omega  -90.00  -34.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -37.0000 -120.0000 56

  6 omega  -83.00  -57.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  -30.0000 26

  7 omega  -43.00    3.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   90.0000 46

  8 omega   35.00   69.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -       19.2147  178.0000 -120.0000 34

  9 omega   30.00   56.00   1.0000   21.4500
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -19.0000  -30.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0236305000
_diffrn_orient_matrix_UB_12      0.0252365000
_diffrn_orient_matrix_UB_13      0.0264974000
_diffrn_orient_matrix_UB_21      0.0288524000
_diffrn_orient_matrix_UB_22      -0.0134531000
_diffrn_orient_matrix_UB_23      0.0536779000
_diffrn_orient_matrix_UB_31      0.0868624000
_diffrn_orient_matrix_UB_32      0.0113368000
_diffrn_orient_matrix_UB_33      0.0046946000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15136
_diffrn_reflns_theta_full        29.18
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88457
_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    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0033(10)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.167
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                3133
_reflns_number_total             4947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc06206b2.cif
_cod_data_source_block           mb-ttr-b-19-g
_cod_depositor_comments
'Adding full bibliography for 1568529--1568531.cif.'
_cod_database_code               1568529
_chemical_oxdiff_formula         'C10 H8 N2 O4'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 295K, 0.55 0.38 0.2'
_reflns_odcompleteness_completeness 99.43
_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:
 C8(H8A,H8B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C4(H4), C18(H18), C19(H19), C20(H20), C7(H7), C17(H17),
 C5(H5), C16(H16), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'