[Pd]-Catalyzed <i>para</i>-selective allylation of phenols: access to 4-[(<i>E</i>)-3-aryl/alkylprop-2-enyl]phenols.
Chinnabattigalla, Sreenivasulu; Choudhury, Aditya; Gedu, Satyanarayana; Organic & biomolecular chemistry 19 (2021) 8259–8263; doi:10.1039/d1ob01489g

data_7158281
_publ_section_title
;
 [Pd]-Catalyzed <i>para</i>-selective allylation of phenols: access to
 4-[(<i>E</i>)-3-aryl/alkylprop-2-enyl]phenols.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8259
_journal_page_last               8263
_journal_paper_doi               10.1039/d1ob01489g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H18 O'
_chemical_formula_sum            'C17 H18 O'
_chemical_formula_weight         238.31
_chemical_name_systematic        GSCBS5_265
_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             2020-12-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                72.77(5)
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.787(7)
_cell_length_b                   13.87(2)
_cell_length_c                   21.66(2)
_cell_measurement_reflns_used    194
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      17.32
_cell_measurement_theta_min      2.94
_cell_volume                     1374(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2286
_diffrn_reflns_av_unetI/netI     0.8537
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7877
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.860
_diffrn_reflns_theta_min         1.969
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5774
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.7745.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method 'DCM +Hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.838
_refine_ls_R_factor_all          0.5151
_refine_ls_R_factor_gt           0.1342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2736
_refine_ls_wR_factor_ref         0.5038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                745
_reflns_number_total             5234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01489g2.cif
_cod_data_source_block           mo_gscbs5_265_2_0ma
_cod_depositor_comments
;
Adding full bibliography for 7158281--7158283.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H36 O2'
_cod_original_formula_weight         476.63
_cod_original_formula_moiety         '2(C17 H18 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1373(3)
_cod_database_code               7158281
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C4(H4), C23(H23), C6(H6), C26(H26), C9(H9), C25(H25),
 C21(H21), C8(H8), C32(H32), C15(H15), C12(H12), C29(H29), C30(H30), C13(H13),
 C14(H14), C31(H31)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C33(H33A,H33B,H33C), C16(H16A,H16B,
 H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_shelx_res_checksum              66142
_olex2_exptl_crystal_mounting_method 'IN ACRYOLOOP WITH MINERAL OIL'
_olex2_submission_original_sample_id GSCBS5_265
_olex2_submission_special_instructions 'No special instructions were received'