Copper(II)-photocatalyzed decarboxylative oxygenation of carboxylic acids.
Reichle, Alexander; Sterzel, Hannes; Kreitmeier, Peter; Fayad, Remi; Castellano, Felix N.; Rehbein, Julia; Reiser, Oliver; Chemical communications (Cambridge, England) 58 (2022) 4456–4459; doi:10.1039/d2cc00570k

data_7129720
_publ_section_title
;
 Copper(II)-photocatalyzed decarboxylative oxygenation of carboxylic
 acids.
;
_journal_issue                   28
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4456
_journal_page_last               4459
_journal_paper_doi               10.1039/d2cc00570k
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_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
_audit_creation_date             2021-07-30
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3024(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.06989(7)
_cell_length_b                   7.09422(3)
_cell_length_c                   26.42930(11)
_cell_measurement_reflns_used    41275
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.2280
_cell_measurement_theta_min      2.7210
_cell_volume                     3012.99(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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     49.00  74.00   0.50    0.50    --   34.00  36.00-161.82   50
  2  \w     53.00  78.00   0.50    0.50    --   38.00  36.00-156.12   50
  3  \w     57.00  82.00   0.50    0.50    --   42.00  36.00-147.85   50
  4  \w     49.00  75.00   0.50    0.50    --   77.75-157.00  43.87   52
  5  \w     68.00 111.00   0.50    0.50    --   77.75-144.00 172.69   86
  6  \w     85.00 111.00   0.50    0.50    --   77.75-157.00  43.87   52
  7  \w     44.00  71.00   0.50    0.50    --   75.18-125.00 -30.00   54
  8  \w     40.00  67.00   0.50    0.50    --   77.75-131.00 -66.80   54
  9  \w     68.00  94.00   0.50    0.50    --   77.75-131.00 -66.80   52
 10  \w     45.00  87.00   0.50    0.50    --   77.75-149.00-142.77   84
 11  \w     40.00  65.00   0.50    0.50    --   75.18-125.00-180.00   50
 12  \w     62.00  98.00   0.50    0.50    --   75.18-125.00-120.00   72
 13  \w     48.00  79.00   0.50    0.50    --   75.18-125.00-150.00   62
 14  \w     47.00  72.00   0.50    0.50    --   75.18-125.00 -90.00   50
 15  \w     39.00  71.00   0.50    0.50    --   75.18-125.00  30.00   64
 16  \w     25.00  50.00   0.50    0.50    --   62.55-125.00  30.00   50
 17  \w     39.00  72.00   0.50    0.50    --   75.18-125.00  60.00   66
 18  \w     37.00  63.00   0.50    0.50    --   62.55-125.00  60.00   52
 19  \w     49.00  99.00   0.50    0.50    --   75.18-125.00 120.00  100
 20  \w     41.00  76.00   0.50    0.50    --   75.18-125.00   0.00   70
 21  \w     24.00  50.00   0.50    0.50    --   62.55-125.00 -30.00   52
 22  \w     24.00  63.00   0.50    0.50    --   62.55-125.00 -60.00   78
 23  \w     25.00  50.00   0.50    0.50    --   62.55-125.00-180.00   50
 24  \w     41.00 100.00   0.50    0.50    --   77.75-123.00 -69.54  118
 25  \w     43.00  83.00   0.50    0.50    --   77.75-117.00  11.73   80
 26  \w     69.00 100.00   0.50    0.50    --   77.75-121.00  93.80   62
 27  \w     89.00 114.00   0.50    0.50    --   77.75 118.00 137.63   50
 28  \w     14.00  40.00   0.50    0.50    --   14.00  92.00 145.36   52
 29  \w    -88.00 -63.00   0.50    0.50    --  -46.00 -36.00  93.78   50
 30  \w    -91.00 -65.00   0.50    0.50    --  -50.00 -35.00  83.99   52
 31  \w    -88.00 -62.00   0.50    0.50    --  -46.00 -35.00 113.42   52
 32  \w    -88.00 -62.00   0.50    0.50    --  -46.00 -36.00 124.70   52
 33  \w    -87.00 -62.00   0.50    0.50    --  -46.00 -36.00 151.75   50
 34  \w   -101.00 -76.00   0.50    0.50    --  -58.00 -38.00  88.03   50
 35  \w   -100.00 -74.00   0.50    0.50    --  -58.00 -35.00 140.84   52
 36  \w   -114.00 -88.00   0.50    0.50    --  -74.00 -34.00 124.46   52
 37  \w    -96.00 -71.00   0.50    0.50    --  -54.00 -36.00  75.02   50
 38  \w   -113.00 -88.00   0.50    0.50    --  -74.00 -34.00   3.07   50
 39  \w   -107.00 -81.00   0.50    0.50    --  -66.00 -34.00  69.26   52
 40  \w   -112.00 -81.00   0.50    0.50    --  -70.00 -30.00 157.81   62
 41  \w   -106.00 -80.00   0.50    0.50    --  -74.00 -91.00 170.79   52
 42  \w   -105.00 -80.00   0.50    0.50    --  -74.00 -91.00 177.41   50
 43  \w   -106.00 -80.00   0.50    0.50    --  -74.00 -91.00 144.81   52
 44  \w   -106.00 -80.00   0.50    0.50    --  -74.00 -91.00 163.05   52
 45  \w    -93.00 -59.00   0.50    0.50    --  -74.00-149.00-105.89   68
 46  \w   -103.00 -78.00   0.50    0.50    --  -74.00-158.00-152.33   50
 47  \w   -108.00 -83.00   0.50    0.50    --  -74.00-108.00-133.88   50
 48  \w   -105.00 -80.00   0.50    0.50    --  -74.00 -91.00-177.98   50
 49  \w   -106.00 -80.00   0.50    0.50    --  -74.00 -91.00-135.19   52
 50  \w   -106.00 -81.00   0.50    0.50    --  -74.00 -91.00 162.08   50
 51  \w   -106.00 -81.00   0.50    0.50    --  -74.00 -91.00 128.88   50
 52  \w   -103.00 -77.00   0.50    0.50    --  -74.00 140.00  24.42   52
 53  \w    -83.00 -43.00   0.50    0.50    --  -74.00 136.00 -58.59   80
 54  \w    -91.00 -36.00   0.50    0.50    --  -70.00 121.00-103.70  110
 55  \w    -90.00 -30.00   0.50    0.50    --  -68.39 125.00  30.00  120
 56  \w    -68.00 -32.00   0.50    0.50    --  -64.12 125.00  90.00   72
 57  \w     74.00  99.00   0.50    0.50    --   77.75  25.00 176.95   50
 58  \w     72.00 117.00   0.50    0.50    --   77.75  20.00 157.71   90
 59  \w     65.00 106.00   0.50    0.50    --   77.75  21.00 122.37   82
 60  \w     66.00 119.00   0.50    0.50    --   77.75  20.00  15.06  106
 61  \w     65.00 102.00   0.50    0.50    --   77.75  21.00 -24.58   74
 62  \w     94.00 119.00   0.50    0.50    --   77.75  18.00 -63.03   50
 63  \w     74.00 111.00   0.50    0.50    --   77.75  25.00-167.20   74
 64  \w     75.00 113.00   0.50    0.50    --   77.75  23.00-125.00   76
 65  \w     52.00  77.00   0.50    0.50    --   77.75  18.00 -63.03   50
 66  \w     64.00  89.00   0.50    0.50    --   77.75  16.00   8.66   50
 67  \w     51.00 101.00   0.50    0.50    --   77.75  17.00  88.34  100
 68  \w     36.00 100.00   0.50    0.50    --   62.55  15.00 120.00  128
 69  \w     45.00  73.00   0.50    0.50    --   62.55  15.00  60.00   56
 70  \w     61.00 104.00   0.50    0.50    --   77.75   9.00   8.34   86
 71  \w     38.00  70.00   0.50    0.50    --   62.55  15.00-180.00   64
 72  \w     75.00 103.00   0.50    0.50    --   62.55  15.00-180.00   56
 73  \w     61.00  87.00   0.50    0.50    --   77.75  12.00-179.79   52
 74  \w     61.00  87.00   0.50    0.50    --   77.75   8.00-178.48   52
 75  \w     68.00  94.00   0.50    0.50    --   77.75   7.00-120.61   52
 76  \w     62.00 112.00   0.50    0.50    --   77.75   3.00 -93.67  100
 77  \w     51.00  94.00   0.50    0.50    --   77.75   7.00 -48.53   86
 78  \w     67.00 105.00   0.50    0.50    --   77.75   4.00 111.01   76
 79  \w     61.00  86.00   0.50    0.50    --   77.75   3.00 123.98   50
 80  \w     68.00  94.00   0.50    0.50    --   77.75   3.00  65.82   52
 81  \w     61.00 109.00   0.50    0.50    --   77.75   3.00-164.36   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0799933000
_diffrn_orient_matrix_UB_12      0.1143407000
_diffrn_orient_matrix_UB_13      0.0092878000
_diffrn_orient_matrix_UB_21      -0.0338569000
_diffrn_orient_matrix_UB_22      -0.0613865000
_diffrn_orient_matrix_UB_23      -0.0520938000
_diffrn_orient_matrix_UB_31      -0.0405311000
_diffrn_orient_matrix_UB_32      -0.1741252000
_diffrn_orient_matrix_UB_33      0.0244630000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            66058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.433
_diffrn_reflns_theta_min         2.750
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.377
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0407P)^2^+1.2798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5835
_reflns_number_total             6106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00570k2.cif
_cod_data_source_block           u082
_cod_depositor_comments
'Adding full bibliography for 7129719--7129722.cif.'
_cod_database_code               7129720
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H14 Cl N O3'
_chemical_oxdiff_usercomment     Reichle_Reiser_AR-1178
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.815
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C3(H3), C25(H25), C33(H33), C29(H29), C8(H8), C32(H32),
 C10(H10), C36(H36), C11(H11), C35(H35), C15(H15), C14(H14), C18(H18), C17(H17)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              85922
_olex2_date_sample_submission    2021-07-29
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id AR-1178
_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.882