Synthesis of trans-Stilbenes via Phosphine-Catalyzed Coupling Reaction of Benzylic Halides
Zhang, Sheng; Xie, Zhilong; Ye, Zhanqiang; Zhang, Mingyang; Li, Dongdeng; Yamaguchi, Masahiko; Bao, Ming; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01237E

data_7158817
_publ_section_title
;
 Synthesis of trans-Stilbenes via Phosphine-Catalyzed Coupling Reaction of
 Benzylic Halides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01237E
_journal_year                    2022
_chemical_formula_moiety         '0.09(C18 H16 O4)'
_chemical_formula_sum            'C H O'
_chemical_formula_weight         29.02
_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             2021-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.036(12)
_cell_angle_gamma                90
_cell_formula_units_Z            43
_cell_length_a                   6.0447(17)
_cell_length_b                   7.273(2)
_cell_length_c                   33.480(10)
_cell_measurement_reflns_used    2203
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.53
_cell_measurement_theta_min      2.43
_cell_volume                     1471.9(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      295.9
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_unetI/netI     0.1394
_diffrn_reflns_Laue_measured_fraction_full 0.917
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            15071
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.660
_diffrn_reflns_theta_min         2.433
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5391
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.7230.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             645
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0309P)^2^+0.4339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.2054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2505
_reflns_number_total             6029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01237e2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1471.9(8)
_cod_database_code               7158817
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00F(H00F), C00L(H00L), C00M(H00M),
 C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012),
 C013(H013), C014(H014)
2.b Idealised Me refined as rotating group:
 C015(H01A,H01B,H01C), C016(H01J,H01K,H01L), C017(H01D,H01E,H01F), C018(H01G,
 H01H,H01I)
;
_shelx_res_checksum              30629
_olex2_submission_special_instructions 'No special instructions were received'