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_7129721
_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         'C15 H10 O3'
_chemical_formula_sum            'C15 H10 O3'
_chemical_formula_weight         238.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-26
_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                90
_cell_angle_beta                 91.551(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7617(9)
_cell_length_b                   8.1050(4)
_cell_length_c                   19.5997(12)
_cell_measurement_reflns_used    7198
_cell_measurement_temperature    122.97(10)
_cell_measurement_theta_max      73.2260
_cell_measurement_theta_min      4.4780
_cell_volume                     2185.3(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 1.3-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      122.97(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 0.970
_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     46.00  77.00   0.50    0.70    --   38.00  67.00  85.75   62
  2  \w     66.00  97.00   0.50    0.70    --   58.00  68.00 102.00   62
  3  \w     88.00 120.00   0.50    2.00    --   76.92  54.00  78.70   64
  4  \w     69.00 124.00   0.50    2.00    --   76.92  25.00  64.97  110
  5  \w     57.00 116.00   0.50    0.70    --   68.89  24.00 120.32  118
  6  \w     51.00 115.00   0.50    0.70    --   68.89  21.00 168.51  128
  7  \w     85.00 124.00   0.50    2.00    --   76.92  34.00   3.39   78
  8  \w     44.00 120.00   0.50    2.00    --   75.21  15.00-180.00  152
  9  \w     61.00  92.00   0.50    0.70    --   54.00  71.00-132.06   62
 10  \w      6.00  33.00   0.50    0.70    --   14.00  94.00-114.27   54
 11  \w     32.00 104.00   0.50    2.00    --   75.21-125.00-120.00  144
 12  \w     34.00 107.00   0.50    2.00    --   76.92-129.00-178.89  146
 13  \w     19.00  91.00   0.50    0.70    --   62.57-125.00  90.00  144
 14  \w     32.00 104.00   0.50    2.00    --   75.21-125.00 -60.00  144
 15  \w     19.00  91.00   0.50    0.70    --   62.57-125.00 -30.00  144
 16  \w     32.00 104.00   0.50    2.00    --   75.21-125.00   0.00  144
 17  \w      1.00  28.00   0.50    0.70    --   10.00  96.00  43.07   54
 18  \w   -115.00 -39.00   0.50    0.70    --  -70.24 -15.00-150.00  152
 19  \w   -116.00 -82.00   0.50    0.70    --  -70.00 -42.00-158.06   68
 20  \w    -96.00 -65.00   0.50    0.70    --  -58.00 -71.00 -32.30   62
 21  \w   -111.00 -79.00   0.50    0.70    --  -70.00 -62.00  13.83   64
 22  \w   -107.00 -75.00   0.50    0.70    --  -66.00 -61.00 117.39   64
 23  \w   -106.00 -75.00   0.50    0.70    --  -70.00 -74.00 162.36   62
 24  \w    -79.00 -48.00   0.50    0.70    --  -42.00 -72.00 -27.40   62
 25  \w    -99.00 -26.00   0.50    0.70    --  -70.24 125.00 -30.00  146
 26  \w    -99.00 -26.00   0.50    0.70    --  -70.24 125.00  60.00  146
;
_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      -0.1095947000
_diffrn_orient_matrix_UB_12      -0.0382799000
_diffrn_orient_matrix_UB_13      -0.0055731000
_diffrn_orient_matrix_UB_21      -0.0184066000
_diffrn_orient_matrix_UB_22      0.1189576000
_diffrn_orient_matrix_UB_23      0.0592781000
_diffrn_orient_matrix_UB_31      -0.0139584000
_diffrn_orient_matrix_UB_32      0.1432226000
_diffrn_orient_matrix_UB_33      -0.0513428000
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11611
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.956
_diffrn_reflns_theta_min         4.514
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_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_density_diffrn    1.448
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0504P)^2^+3.9222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             2140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00570k2.cif
_cod_data_source_block           u064
_cod_depositor_comments
'Adding full bibliography for 7129719--7129722.cif.'
_cod_database_code               7129721
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H10 O3'
_chemical_oxdiff_usercomment     Reichle_Reiser_AR1091
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.872
_reflns_odcompleteness_completeness 100.00
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C6(H6), C7(H7), C14(H14), C12(H12), C13(H13), C1(H1)
;
_shelx_res_checksum              92179
_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.643