Direct decarboxylative Giese amidations: photocatalytic <i>vs.</i> metal- and light-free.
Kitcatt, David M.; Scott, Katie A.; Rongione, Elena; Nicolle, Simon; Lee, Ai-Lan; Chemical science 14 (2023) 9806–9813; doi:10.1039/d3sc03143h

data_1569712
_publ_section_title
;
 Direct decarboxylative Giese amidations: photocatalytic <i>vs.</i> metal-
 and light-free.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              9806
_journal_page_last               9813
_journal_paper_doi               10.1039/d3sc03143h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-21 deposited with the CCDC.	2023-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.7432(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.20570(10)
_cell_length_b                   20.7249(5)
_cell_length_c                   12.8023(3)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.144
_cell_measurement_theta_min      3.503
_cell_volume                     1361.29(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37605
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_min         3.503
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0950 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.8502.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.951
_refine_diff_density_min         -1.856
_refine_diff_density_rms         0.253
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     415
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2050
_refine_ls_R_factor_gt           0.1991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.5000P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5464
_refine_ls_wR_factor_ref         0.5539
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4888
_reflns_number_total             5348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03143h2.cif
_cod_data_source_block           cu_8v00967_0m_a
_cod_depositor_comments          'Adding full bibliography for 1569712.cif.'
_cod_database_code               1569712
_shelx_shelxl_version_number     2018/3
_publcif_funding_html
;
;
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.842
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(11)
 -0.2(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C6') \\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C13')
\\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2') \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(O11)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C9) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C6') \\sim Ueq, Uanis(O1') \\sim Ueq, Uanis(C7') \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C6) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O1, O2, O8, O11, O1', O2', O8', O11', C1, C3, C4, C5, C6, C7, C9, C10, C11,
 C13, C14, C15, C16, C17, C18, C1', C3', C4', C5', C6', C7', C9', C10', C11',
 C13', C14', C15', C16', C17', C18', N12, N12'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C3'(H3'), C4'(H4'), C7'(H7')
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C5'(H5'A,H5'B)
5.c Aromatic/amide H refined with riding coordinates:
 N12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), N12'(H12'),
 C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18')
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C9'(H9'A,H9'B,H9'C), C10'(H10D,H10E,H10F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              7442
_olex2_submission_special_instructions 'No special instructions were received'