Carboamination and olefination: <i>ortho</i> C-H functionalization of phenoxyacetamide.
Nanda, Tanmayee; Dhal, Shubham Kumar; Das Adhikari, Gopal Krushna; Prusty, Namrata; Ravikumar, Ponneri C.; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02202a

data_7131754
_publ_section_title
;
 Carboamination and olefination: <i>ortho</i> C-H functionalization of
 phenoxyacetamide.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02202a
_journal_year                    2023
_chemical_formula_moiety         'C26 H27 N O6'
_chemical_formula_sum            'C26 H27 N O6'
_chemical_formula_weight         449.48
_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             2022-10-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-10-12 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.905(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1511(6)
_cell_length_b                   11.6784(4)
_cell_length_c                   14.2759(6)
_cell_measurement_reflns_used    18168
_cell_measurement_temperature    297.6(7)
_cell_measurement_theta_max      30.6430
_cell_measurement_theta_min      3.4390
_cell_volume                     2279.89(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_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      297.6(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.867
_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     -5.00  47.00   0.50   16.98    --    3.51-112.00  -7.00  104
  2  \w     -8.00  66.00   0.50   16.98    --    3.51  57.00  60.00  148
  3  \w    -59.00  15.00   0.50   16.98    --    3.51 -57.00 -30.00  148
  4  \w      0.00  70.00   0.50   16.98    --    3.51  37.00-180.00  140
  5  \w    -42.00  27.00   0.50   16.98    --    3.51 -77.00 -90.00  138
  6  \w     -8.00  66.00   0.50   16.98    --    3.51  57.00 150.00  148
  7  \w    -63.00   3.00   0.50   16.98    --    3.51 -37.00 -30.00  132
  8  \w    -42.00  17.00   0.50   16.98    --   -4.14 -77.00-120.00  118
  9  \w     37.00  62.00   0.50   16.98    --   -4.14  37.00  90.00   50
 10  \w      3.00  29.00   0.50   16.98    --   -4.14  37.00  90.00   52
 11  \w    -16.00  18.00   0.50   16.98    --   -4.14 -77.00 120.00   68
 12  \w      6.00  31.00   0.50   16.98    --   -4.14 -99.00 -60.00   50
 13  \w     -7.00  61.00   0.50   16.98    --   -4.14  37.00  60.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0213985000
_diffrn_orient_matrix_UB_12      0.0413387000
_diffrn_orient_matrix_UB_13      0.0246323000
_diffrn_orient_matrix_UB_21      -0.0113242000
_diffrn_orient_matrix_UB_22      -0.0436950000
_diffrn_orient_matrix_UB_23      0.0298976000
_diffrn_orient_matrix_UB_31      0.0458609000
_diffrn_orient_matrix_UB_32      0.0085197000
_diffrn_orient_matrix_UB_33      0.0337961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50828
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.469
_diffrn_reflns_theta_min         3.424
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0571P)^2^+0.3480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4340
_reflns_number_total             6015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02202a2.cif
_cod_data_source_block           tn-2932_auto
_cod_database_code               7131754
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O '
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.74
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C24(H24A,H24B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C15(H15), C11(H11), C3(H3), C12(H12), C14(H14), C13(H13)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_shelx_res_checksum              94188
_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.660