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_7129722
_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         'C40 H42 Cu2 N2 O12'
_chemical_formula_sum            'C40 H42 Cu2 N2 O12'
_chemical_formula_weight         869.84
_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     dual
_audit_creation_date             2021-05-27
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                83.192(2)
_cell_angle_beta                 85.2690(10)
_cell_angle_gamma                88.081(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8246(2)
_cell_length_b                   13.6030(3)
_cell_length_c                   14.54570(10)
_cell_measurement_reflns_used    22042
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      71.4280
_cell_measurement_theta_min      3.0260
_cell_volume                     1923.11(6)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-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      123.01(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 0.990
_diffrn_measured_fraction_theta_max 0.946
_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  22.00   0.50    0.70    --    6.00  99.00   7.56   54
  2  \w     -6.00  23.00   0.50    0.70    --   -6.00  82.00-157.23   58
  3  \w      0.00  25.00   0.50    0.70    --   10.00  98.00-106.27   50
  4  \w      9.00  34.00   0.50    0.70    --   14.00  90.00 112.04   50
  5  \w     14.00  39.00   0.50    0.70    --   18.00  89.00 -29.86   50
  6  \w     16.00  41.00   0.50    0.70    --   18.00  86.00  62.34   50
  7  \w     16.00  41.00   0.50    0.70    --   18.00  85.00 123.56   50
  8  \w     16.00  41.00   0.50    0.70    --   18.00  85.00 -85.28   50
  9  \w     13.00  39.00   0.50    0.70    --   18.00  91.00 163.22   52
 10  \w    -43.00 -18.00   0.50    0.70    --  -22.00 122.00 137.58   50
 11  \w     25.00  50.00   0.50    0.70    --   22.00  77.00-119.31   50
 12  \w    -54.00 -26.00   0.50    0.70    --  -22.00 -76.00 -68.10   56
 13  \w     30.00  55.00   0.50    0.70    --   26.00  76.00  24.91   50
 14  \w     30.00  55.00   0.50    0.70    --   26.00  76.00 -67.81   50
 15  \w     30.00  55.00   0.50    0.70    --   26.00  76.00 -40.51   50
 16  \w     34.00  59.00   0.50    0.70    --   26.00  68.00  19.04   50
 17  \w     34.00  59.00   0.50    0.70    --   26.00  69.00 159.50   50
 18  \w     33.00  58.00   0.50    0.70    --   30.00  77.00-106.65   50
 19  \w    -62.00 -35.00   0.50    0.70    --  -30.00 -76.00 161.36   54
 20  \w    -27.00   0.00   0.50    0.70    --  -30.00 107.00  18.49   54
 21  \w     35.00  60.00   0.50    0.70    --   30.00  75.00 -35.76   50
 22  \w     39.00  64.00   0.50    0.70    --   34.00  75.00  57.60   50
 23  \w     42.00  67.00   0.50    0.70    --   34.00  67.00-164.59   50
 24  \w     41.00  66.00   0.50    0.70    --   34.00  70.00  96.52   50
 25  \w     37.00  62.00   0.50    0.70    --   34.00  77.00 118.11   50
 26  \w     40.00  65.00   0.50    0.70    --   34.00  73.00 -15.00   50
 27  \w     39.00  64.00   0.50    0.70    --   34.00  74.00-116.09   50
 28  \w     41.00  66.00   0.50    0.70    --   38.00  77.00 154.66   50
 29  \w     43.00  68.00   0.50    0.70    --   38.00  74.00 -78.77   50
 30  \w     42.00  69.00   0.50    0.70    --   38.00  77.00  24.41   54
 31  \w     43.00  68.00   0.50    0.70    --   38.00  74.00-160.29   50
 32  \w    -75.00 -48.00   0.50    0.70    --  -42.00 -72.00  64.90   54
 33  \w     48.00  73.00   0.50    0.70    --   42.00  72.00-160.07   50
 34  \w     50.00  75.00   0.50    0.70    --   42.00  69.00-129.10   50
 35  \w     48.00  73.00   0.50    0.70    --   42.00  72.00 175.57   50
 36  \w     48.00  73.00   0.50    0.70    --   42.00  72.00 139.25   50
 37  \w     49.00  74.00   0.50    0.70    --   42.00  70.00  -5.07   50
 38  \w     50.00  75.00   0.50    0.70    --   42.00  69.00 -46.88   50
 39  \w     49.00  74.00   0.50    0.70    --   42.00  71.00 -98.38   50
 40  \w     51.00  76.00   0.50    0.70    --   42.00  63.00  71.13   50
 41  \w     50.00  75.00   0.50    0.70    --   42.00  69.00  17.74   50
 42  \w     54.00  79.00   0.50    0.70    --   46.00  68.00  69.25   50
 43  \w     53.00  78.00   0.50    0.70    --   46.00  70.00 178.67   50
 44  \w    -80.00 -53.00   0.50    0.70    --  -50.00 -77.00   7.28   54
 45  \w     58.00  83.00   0.50    0.70    --   50.00  66.00  85.95   50
 46  \w     58.00  83.00   0.50    0.70    --   50.00  67.00  16.71   50
 47  \w     61.00  86.00   0.50    0.70    --   54.00  71.00  13.66   50
 48  \w    -87.00 -60.00   0.50    0.70    --  -54.00 -72.00 104.45   54
 49  \w    -87.00 -60.00   0.50    0.70    --  -54.00 -72.00 -54.01   54
 50  \w     63.00  88.00   0.50    0.70    --   54.00  63.00-177.17   50
 51  \w     61.00  86.00   0.50    0.70    --   54.00  70.00-149.98   50
 52  \w    -86.00 -60.00   0.50    0.70    --  -54.00 -72.00 -28.19   52
 53  \w    -98.00 -70.00   0.50    0.70    --  -58.00 -61.00 -63.44   56
 54  \w     66.00  91.00   0.50    0.70    --   58.00  69.00  99.55   50
 55  \w     64.00  89.00   0.50    0.70    --   58.00  72.00 -63.02   50
 56  \w     65.00  90.00   0.50    0.70    --   58.00  70.00  47.42   50
 57  \w     67.00  92.00   0.50    0.70    --   58.00  61.00  50.06   50
 58  \w     65.00  90.00   0.50    0.70    --   58.00  70.00-153.71   50
 59  \w     65.00  90.00   0.50    0.70    --   58.00  70.00  92.35   50
 60  \w     67.00  92.00   0.50    0.70    --   58.00  62.00 -79.82   50
 61  \w     66.00  91.00   0.50    0.70    --   58.00  69.00 -77.48   50
 62  \w     66.00  91.00   0.50    0.70    --   58.00  69.00-171.36   50
 63  \w    -92.00 -65.00   0.50    0.70    --  -58.00 -69.00  12.43   54
 64  \w     66.00  91.00   0.50    0.70    --   58.00  68.00-124.44   50
 65  \w     64.00  89.00   0.50    0.70    --   58.00  72.00 138.99   50
 66  \w     68.00  93.00   0.50    0.70    --   62.00  72.00  78.22   50
 67  \w     70.00 100.00   0.50    0.70    --   62.00  71.00-172.37   60
 68  \w     69.00  94.00   0.50    0.70    --   62.00  70.00 -58.46   50
 69  \w     69.00  94.00   0.50    0.70    --   62.00  71.00-107.63   50
 70  \w   -100.00 -69.00   0.50    0.70    --  -62.00 -71.00  12.15   62
 71  \w     20.00  47.00   0.50    0.70    --   62.57-125.00  60.00   54
 72  \w     20.00  47.00   0.50    0.70    --   62.57-125.00   0.00   54
 73  \w     75.00 102.00   0.50    0.70    --   62.57  15.00-150.00   54
 74  \w     31.00  72.00   0.50    0.70    --   62.57  15.00-150.00   82
 75  \w     20.00  58.00   0.50    0.70    --   62.57-125.00-150.00   76
 76  \w     19.00  90.00   0.50    0.70    --   62.57-125.00 -90.00  142
 77  \w     24.00  50.00   0.50    0.70    --   62.57-125.00 -60.00   52
 78  \w     19.00  67.00   0.50    0.70    --   62.57-125.00  90.00   96
 79  \w     19.00  79.00   0.50    0.70    --   62.57-125.00 -30.00  120
 80  \w     19.00  89.00   0.50    0.70    --   62.57-125.00 150.00  140
 81  \w     20.00  51.00   0.50    0.70    --   62.57-125.00-120.00   62
 82  \w    -56.00 -22.00   0.50    0.70    --  -64.16 125.00  30.00   68
 83  \w     71.00 103.00   0.50    0.70    --   66.00  74.00 133.52   64
 84  \w   -101.00 -75.00   0.50    0.70    --  -66.00 -59.00  92.12   52
 85  \w     44.00 114.00   0.50    0.70    --   68.89  19.00  67.32  140
 86  \w     84.00 113.00   0.50    0.70    --   68.89  20.00  -7.06   58
 87  \w     49.00  76.00   0.50    0.70    --   68.89  20.00  -7.06   54
 88  \w   -104.00 -75.00   0.50    0.70    --  -70.00 -74.00-117.89   58
 89  \w   -102.00 -75.00   0.50    0.70    --  -70.00 -73.00-161.05   54
 90  \w   -105.00 -79.00   0.50    0.70    --  -70.00 -64.00 -28.07   52
 91  \w   -103.00 -75.00   0.50    0.70    --  -70.00 -73.00 -32.94   56
 92  \w   -105.00 -76.00   0.50    0.70    --  -70.00 -72.00  58.96   58
 93  \w   -106.00 -77.00   0.50    0.70    --  -70.00 -71.00 151.13   58
 94  \w   -101.00 -75.00   0.50    0.70    --  -70.00 -74.00   2.46   52
 95  \w   -103.00 -75.00   0.50    0.70    --  -70.00 -74.00 -57.04   56
 96  \w    -72.00 -29.00   0.50    0.70    --  -70.24 125.00 -60.00   86
 97  \w    -81.00 -39.00   0.50    0.70    --  -70.24 -15.00   0.00   84
 98  \w    -54.00 -27.00   0.50    0.70    --  -70.24 125.00 -30.00   54
 99  \w    -99.00 -61.00   0.50    0.70    --  -70.24 125.00 -30.00   76
100  \w    -98.00 -26.00   0.50    0.70    --  -70.24 125.00-150.00  144
101  \w    -62.00 -26.00   0.50    0.70    --  -70.24 125.00 -90.00   72
102  \w    -58.00 -27.00   0.50    0.70    --  -70.24 125.00  90.00   62
103  \w    -99.00 -72.00   0.50    0.70    --  -70.24 125.00  90.00   54
104  \w    -97.00 -26.00   0.50    0.70    --  -70.24 125.00 120.00  142
105  \w    -72.00 -45.00   0.50    0.70    --  -70.58 -19.00 177.78   54
106  \w   -115.00 -76.00   0.50    0.70    --  -70.58 -19.00 177.78   78
107  \w     32.00  81.00   0.50    0.70    --   72.44-125.00-180.00   98
108  \w   -107.00 -78.00   0.50    2.00    --  -74.00 -75.00-121.51   58
109  \w   -107.00 -79.00   0.50    2.00    --  -74.00 -73.00 170.30   56
110  \w     38.00  99.00   0.50    2.00    --   75.21-125.00  90.00  122
111  \w     38.00 104.00   0.50    2.00    --   75.21-125.00-120.00  132
112  \w     79.00 104.00   0.50    2.00    --   75.21-125.00 -60.00   50
113  \w     35.00  60.00   0.50    2.00    --   75.21-125.00 -60.00   50
114  \w     35.00 104.00   0.50    2.00    --   75.21-125.00   0.00  138
115  \w     33.00 104.00   0.50    2.00    --   75.21-125.00 150.00  142
116  \w     33.00 104.00   0.50    2.00    --   75.21-125.00 120.00  142
117  \w     55.00 119.00   0.50    2.00    --   75.21  15.00 120.00  128
118  \w     45.00  95.00   0.50    2.00    --   75.21  15.00 -30.00  100
;
_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      -0.0028540000
_diffrn_orient_matrix_UB_12      0.1135844000
_diffrn_orient_matrix_UB_13      -0.0223636000
_diffrn_orient_matrix_UB_21      -0.0929448000
_diffrn_orient_matrix_UB_22      0.0090283000
_diffrn_orient_matrix_UB_23      0.0893713000
_diffrn_orient_matrix_UB_31      0.1269813000
_diffrn_orient_matrix_UB_32      0.0057743000
_diffrn_orient_matrix_UB_33      0.0544202000
_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  0.0848
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52324
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.028
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_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 blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       plate
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.607
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0843P)^2^+0.7796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5785
_reflns_number_total             7274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00570k2.cif
_cod_data_source_block           u065
_cod_depositor_comments
;
Adding full bibliography for 7129719--7129722.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H21 Cu N O6'
_cod_original_formula_weight         434.92
_cod_original_formula_moiety         '0.5(C40 H42 Cu2 N2 O12)'
_cod_original_formula_units_Z            4
_cod_database_code               7129722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H13 Cu O6'
_chemical_oxdiff_usercomment     Reichle_Reiser_AR-663
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.665
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C24(H24A,H24B), C17(H17A,H17B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C12(H12), C39(H39), C13(H13), C6(H6), C38(H38), C15(H15), C26(H26),
 C36(H36), C30(H30), C29(H29), C16(H16), C4(H4), C27(H27), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C10(H10A,H10B,H10C), C1(H1A,H1B,
 H1C), C31(H31A,H31B,H31C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              68414
_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-663
_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 2.146
_oxdiff_exptl_absorpt_empirical_full_min 0.398