Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO2
Zhou, Chunlin; Wang, Xinchao; Yang, Lei; Fu, Lei; Li, Gang; Green Chemistry 24 (2022) 6100–6107; doi:10.1039/D2GC01256A

data_7244969
_publ_section_title
;
 Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with
 organic halides and CO2
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              6100
_journal_page_last               6107
_journal_paper_doi               10.1039/D2GC01256A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_block_doi                 10.5517/ccdc.csd.cc291rqv
_audit_creation_date             2021-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2022-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.608(2)
_cell_angle_beta                 109.911(2)
_cell_angle_gamma                92.242(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8580(2)
_cell_length_b                   9.5201(2)
_cell_length_c                   9.7104(2)
_cell_measurement_reflns_used    11237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.4980
_cell_measurement_theta_min      4.1470
_cell_volume                     749.00(3)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9864
_diffrn_measured_fraction_theta_max 0.9864
_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     50.00  80.00   0.50    0.05    --   73.53  77.00   0.00   60
  2  \w     52.00  90.00   0.50    0.05    --   73.53  77.00  60.00   76
  3  \w    122.00 147.00   0.50    0.05    --   73.53  77.00 120.00   50
  4  \w    119.00 145.00   0.50    0.05    --   73.53  77.00   0.00   52
  5  \w     50.00  76.00   0.50    0.05    --   73.53  77.00 150.00   52
  6  \w     90.00 146.00   0.50    0.05    --   73.53  77.00 -60.00  112
  7  \w     50.00 147.00   0.50    0.05    --   73.53  77.00-150.00  194
  8  \w    109.00 135.00   0.50    0.05    --   73.53  77.00-180.00   52
  9  \w     50.00  85.00   0.50    0.05    --   73.53  77.00-180.00   70
 10  \w     50.00  75.00   0.50    0.05    --   73.53  77.00-120.00   50
 11  \w     50.00  81.00   0.50    0.05    --   73.53  77.00 -60.00   62
 12  \w     51.00  89.00   0.50    0.05    --   73.53  77.00 -30.00   76
 13  \w     50.00  76.00   0.50    0.05    --   73.53  77.00 -90.00   52
 14  \w     50.00 106.00   0.50    0.05    --   73.53  77.00  30.00  112
 15  \w     50.00  86.00   0.50    0.05    --   73.53  77.00  90.00   72
 16  \w     99.00 140.00   0.50    0.05    --   73.53  77.00  90.00   82
 17  \w    121.00 147.00   0.50    0.05    --   73.53  77.00 150.00   52
 18  \w     50.00 105.00   0.50    0.05    --   73.53  77.00 120.00  110
 19  \w     60.00  96.00   0.50    0.05    --   73.53  38.00   0.00   72
 20  \w     58.00  84.00   0.50    0.05    --   73.53  57.00 -60.00   52
 21  \w     57.00  83.00   0.50    0.05    --   73.53  57.00 -90.00   52
 22  \w     89.00 116.00   0.50    0.05    --   73.53  57.00 -90.00   54
 23  \w    108.00 141.00   0.50    0.05    --   73.53  38.00   0.00   66
 24  \w     67.00  93.00   0.50    0.05    --   73.53-102.00-126.00   52
 25  \w     21.00 105.00   0.50    0.05    --   73.53-125.00 -60.00  168
 26  \w     24.00 110.00   0.50    0.05    --   73.53-125.00 150.00  172
 27  \w     35.00  69.00   0.50    0.05    --   73.53 -38.00  90.00   68
 28  \w     14.00  39.00   0.50    0.05    --   73.53 -38.00 -90.00   50
 29  \w     44.00  71.00   0.50    0.05    --   73.53 -38.00 -90.00   54
 30  \w     92.00 144.00   0.50    0.05    --   73.53 102.00 -23.00  104
 31  \w    -16.00  70.00   0.50    0.05    --   -0.62  57.00-120.00  172
 32  \w    -17.00  58.00   0.50    0.05    --   -0.62  57.00 -30.00  150
 33  \w    -11.00  14.00   0.50    0.05    --   -0.62  38.00  30.00   50
 34  \w    -13.00  12.00   0.50    0.05    --   -0.62  57.00  60.00   50
 35  \w    -14.00  11.00   0.50    0.05    --   -0.62  38.00 120.00   50
 36  \w     15.00  69.00   0.50    0.05    --   -0.62  38.00 120.00  108
 37  \w     24.00  50.00   0.50    0.05    --   -0.62  57.00  60.00   52
 38  \w     39.00  72.00   0.50    0.05    --   -0.62  38.00  30.00   66
 39  \w     14.00  71.00   0.50    0.05    --   -0.62  38.00-180.00  114
 40  \w    -97.00  -6.00   0.50    0.05    --  -74.78  77.00   0.00  182
 41  \w    -91.00  -6.00   0.50    0.05    --  -74.78  57.00-120.00  170
 42  \w    -71.00 -33.00   0.50    0.05    --  -74.78  38.00  90.00   76
 43  \w    -26.00  -1.00   0.50    0.05    --  -74.78  38.00  90.00   50
 44  \w   -110.00 -20.00   0.50    0.05    --  -74.78 125.00  30.00  180
 45  \w    -75.00 -41.00   0.50    0.05    --  -74.78 102.00 -23.00   68
 46  \w    -82.00 -51.00   0.50    0.05    --  -74.78 -77.00 120.00   62
 47  \w   -147.00 -94.00   0.50    0.05    --  -74.78 -77.00 120.00  106
 48  \w   -143.00 -99.00   0.50    0.05    --  -74.78 -77.00 154.19   88
 49  \w    -93.00 -51.00   0.50    0.05    --  -74.78 -77.00 154.19   84
 50  \w   -142.00 -96.00   0.50    0.05    --  -74.78 -77.00 -30.00   92
 51  \w   -137.00-112.00   0.50    0.05    --  -74.78 -46.00  41.33   50
 52  \w    -77.00 -52.00   0.50    0.05    --  -74.78 -77.00 -30.00   50
 53  \w    -88.00 -63.00   0.50    0.05    --  -74.78 -55.00-114.93   50
 54  \w    -87.00 -56.00   0.50    0.05    --  -74.78 -64.00-160.18   62
 55  \w   -106.00 -58.00   0.50    0.05    --  -74.78 -64.00-129.31   96
 56  \w   -137.00 -60.00   0.50    0.05    --  -74.78 -46.00 -11.97  154
 57  \w   -108.00 -59.00   0.50    0.05    --  -74.78 -46.00  41.33   98
 58  \w   -119.00 -60.00   0.50    0.05    --  -74.78 -46.00 142.06  118
 59  \w   -146.00-114.00   0.50    0.05    --  -74.78-125.00  60.00   64
 60  \w   -126.00 -96.00   0.50    0.05    --  -74.78-102.00-126.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1324897000
_diffrn_orient_matrix_UB_12      -0.0364812000
_diffrn_orient_matrix_UB_13      0.0968082000
_diffrn_orient_matrix_UB_21      0.0741039000
_diffrn_orient_matrix_UB_22      0.1336414000
_diffrn_orient_matrix_UB_23      0.0289947000
_diffrn_orient_matrix_UB_31      -0.0562969000
_diffrn_orient_matrix_UB_32      0.0414499000
_diffrn_orient_matrix_UB_33      0.1117455000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19649
_diffrn_reflns_theta_full        60.6394
_diffrn_reflns_theta_max         60.64
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.1809
_exptl_crystal_description       block
_exptl_crystal_F_000             284.6713
_exptl_crystal_size_max          0.033
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.2958
_refine_diff_density_min         -0.2085
_refine_diff_density_rms         0.0404
_refine_ls_d_res_high            0.7690
_refine_ls_d_res_low             9.2615
_refine_ls_goodness_of_fit_ref   1.0649
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0649
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.1405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2753
_reflns_number_total             3409
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc01256a2.cif
_cod_data_source_block           18-16-3A_auto
_cod_depositor_comments
'Adding full bibliography for 7244969--7244970.cif.'
_cod_database_code               7244969
_chemical_oxdiff_formula         CHO
_diffrn_oxdiff_digest_frames
;
01488e73417a8202c0db964033be06647e00042e30e
;
_diffrn_oxdiff_digest_hkl
;
01ba1cef8fadee8c89bb071731024bd763829f
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_olex2_refinement_description
;
;
_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 3.527
_oxdiff_exptl_absorpt_empirical_full_min 0.591