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_1568530
_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         'C27 H23 N O5 S'
_chemical_formula_sum            'C27 H23 N O5 S'
_chemical_formula_weight         473.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-06-11
_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                88.527(4)
_cell_angle_beta                 77.996(4)
_cell_angle_gamma                72.445(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2408(5)
_cell_length_b                   10.2565(5)
_cell_length_c                   15.3407(7)
_cell_measurement_temperature    297.00
_cell_volume                     1208.25(12)
_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      297.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.863
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13468
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         4.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.172
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.0369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                3842
_reflns_number_total             5569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc06206b2.cif
_cod_data_source_block           ttr-b-162-m-pvs
_cod_depositor_comments
'Adding full bibliography for 1568529--1568531.cif.'
_cod_original_cell_volume        1208.25(10)
_cod_database_code               1568530
_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:
 C20C(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C16C(H16C), C14C(H14C), C8C(H8C), C11C(H11C), C10C(H10C), C7C(H7C),
 C26C(H26C), C23C(H23C), C6C(H6C), C2C(H2C), C4C(H4C), C24C(H24C), C25C(H25C),
 C5C(H5C), C3C(H3C)
2.c Idealised Me refined as rotating group:
 C15C(H15A,H15B,H15C), C19C(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'