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_7244970
_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         'C28 H32 O2'
_chemical_formula_sum            'C28 H32 O2'
_chemical_formula_weight         400.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-11-18 deposited with the CCDC.	2022-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.352(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5909(4)
_cell_length_b                   23.7105(9)
_cell_length_c                   10.2921(4)
_cell_measurement_reflns_used    16764
_cell_measurement_temperature    293
_cell_measurement_theta_max      60.6220
_cell_measurement_theta_min      3.2870
_cell_volume                     2245.80(16)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_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    121.00 147.00   0.50    0.14    --   73.53  77.00   0.00   52
  2  \w     50.00  94.00   0.50    0.14    --   73.53  77.00   0.00   88
  3  \w     72.00 142.00   0.50    0.14    --   73.53  38.00 120.00  140
  4  \w     26.00  72.00   0.50    0.05    --   -0.62  77.00   0.00   92
  5  \w    -16.00  23.00   0.50    0.05    --   -0.62  77.00   0.00   78
  6  \w    -84.00  -2.00   0.50    0.14    --  -74.78  57.00 120.00  164
  7  \w    -57.00  -4.00   0.50    0.14    --  -74.78  77.00-150.00  106
  8  \w     26.00  67.00   0.50    0.05    --   -0.62  38.00-120.00   82
  9  \w    102.00 144.00   0.50    0.14    --   73.53 125.00-180.00   84
 10  \w     83.00 137.00   0.50    0.14    --   73.53  90.00 -53.00  108
 11  \w     87.00 147.00   0.50    0.14    --   73.53 125.00  60.00  120
 12  \w      0.00  42.00   0.50    0.14    --   73.53 -38.00   0.00   84
 13  \w      1.00  26.00   0.50    0.14    --   73.53 -38.00-150.00   50
 14  \w     35.00  69.00   0.50    0.14    --   73.53 -38.00-150.00   68
 15  \w      1.00  88.00   0.50    0.14    --   73.53 -57.00-180.00  174
 16  \w     30.00  56.00   0.50    0.14    --   73.53 -90.00-167.00   52
 17  \w     40.00 111.00   0.50    0.14    --   73.53-125.00-150.00  142
 18  \w     30.00 101.00   0.50    0.14    --   73.53-125.00  60.00  142
 19  \w    -34.00  22.00   0.50    0.05    --   -0.62 -90.00-167.00  112
 20  \w   -118.00 -82.00   0.50    0.14    --  -74.78 -90.00-167.00   72
 21  \w   -143.00 -92.00   0.50    0.14    --  -74.78 -99.00 -60.00  102
 22  \w   -126.00-100.00   0.50    0.14    --  -74.78-125.00 150.00   52
 23  \w   -101.00 -54.00   0.50    0.14    --  -74.78  90.00 -53.00   94
 24  \w   -110.00 -64.00   0.50    0.14    --  -74.78 125.00 -60.00   92
 25  \w    -61.00 -20.00   0.50    0.14    --  -74.78 125.00 -60.00   82
 26  \w    -37.00 -11.00   0.50    0.14    --  -74.78  90.00 -53.00   52
 27  \w    -19.00  36.00   0.50    0.05    --   -0.62  90.00 -53.00  110
 28  \w   -109.00 -23.00   0.50    0.14    --  -74.78 125.00  90.00  172
;
_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      0.1264062000
_diffrn_orient_matrix_UB_12      0.0180265000
_diffrn_orient_matrix_UB_13      0.0822924000
_diffrn_orient_matrix_UB_21      -0.0128241000
_diffrn_orient_matrix_UB_22      0.0482021000
_diffrn_orient_matrix_UB_23      -0.0705781000
_diffrn_orient_matrix_UB_31      -0.0707951000
_diffrn_orient_matrix_UB_32      0.0234557000
_diffrn_orient_matrix_UB_33      0.0812891000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.562
_diffrn_reflns_theta_min         3.241
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70741
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0562P)^2^+0.3218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4026
_reflns_number_total             5141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc01256a2.cif
_cod_data_source_block           19-12-4tm_auto
_cod_depositor_comments
'Adding full bibliography for 7244969--7244970.cif.'
_cod_database_code               7244970
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHO
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.922
_diffrn_oxdiff_digest_frames
;
019a39a89ad1970f970c5d2ed95847cb220276648c7
;
_diffrn_oxdiff_digest_hkl
;
010a95a3c3cd620dff5525a2054f858efbf632
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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 Ternary CH refined with riding coordinates:
 C15(H15), C20(H20), C23(H23), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,
 H24B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.644