[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_7158283
_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 H17 Br O'
_chemical_formula_sum            'C17 H17 Br O'
_chemical_formula_weight         317.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.906(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2775(7)
_cell_length_b                   5.2464(5)
_cell_length_c                   17.4065(11)
_cell_measurement_reflns_used    741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5700
_cell_measurement_theta_min      2.6660
_cell_volume                     754.94(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_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    -88.00 -62.00   1.00   25.98    --  -18.08 -77.00 -60.00   26
  2  \w    -10.00  88.00   1.00   25.98    --   19.64  77.00 -30.00   98
  3  \w    -39.00  47.00   1.00   25.98    --   19.64 -77.00-180.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3212
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.619
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.959
_diffrn_reflns_theta_min         2.343
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          1.977
_refine_ls_shift/su_mean         0.087
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.2172
_reflns_Friedel_coverage         0.285
_reflns_Friedel_fraction_full    0.435
_reflns_Friedel_fraction_max     0.307
_reflns_number_gt                1179
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01489g2.cif
_cod_data_source_block           exp_9978
_cod_depositor_comments
'Adding full bibliography for 7158281--7158283.cif.'
_cod_database_code               7158283
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.913
_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:
 C9(H9A,H9B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C14(H14), C13(H13), C16(H16), C11(H11), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
;