A photo- and cobalt-catalyzed highly selective and divergent hydrofunctionalization of 1,3-dienes with phenols.
Wang, Yue; Miao, Junhao; Dong, Honglin; Zhang, Dongliang; Chen, Bei; Guan, Meihui; Zhang, Ge; Zhang, Qian; Chemical science 16 (2025) 5640–5650; doi:10.1039/d5sc00438a

data_1573930
_publ_section_title
;
 A photo- and cobalt-catalyzed highly selective and divergent
 hydrofunctionalization of 1,3-dienes with phenols.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              5640
_journal_page_last               5650
_journal_paper_doi               10.1039/d5sc00438a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C22 H19 Cl O'
_chemical_formula_sum            'C22 H19 Cl O'
_chemical_formula_weight         334.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jxgmk
_audit_creation_date             2024-03-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8872(5)
_cell_length_b                   10.1609(5)
_cell_length_c                   28.5346(12)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.10
_cell_volume                     3446.5(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2103
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.358
_diffrn_reflns_theta_min         3.097
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1504 before and 0.0871 after correction.
The Ratio of minimum to maximum transmission is 0.6906.
The \l/2 correction factor is Not present.
;
_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    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0975P)^2^+0.3910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2818
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00438a2.cif
_cod_data_source_block           22223
_cod_depositor_comments          'Adding full bibliography for 1573930.cif.'
_cod_database_code               1573930
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.797
_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:
 C00J(H00J), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00M(H00M), C00P(H00P), C00R(H00R), C00S(H00S),
 C010(H010), C012(H012), C013(H013), C016(H016), C017(H017), C01B(H01D)
2.d Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C)
;
_shelx_res_checksum              92198
_shelx_hkl_checksum              23001
_olex2_submission_special_instructions 'No special instructions were received'