Biomimetic oxidative dimerization of anodically generated stilbene radical cations: effect of aromatic substitution on product distribution and reaction pathways.
Hong, Fong-Jiao; Low, Yun-Yee; Chong, Kam-Weng; Thomas, Noel F.; Kam, Toh-Seok; The Journal of organic chemistry 79 (2014) 4528–4543; doi:10.1021/jo500559r

data_4029398
_publ_section_title
;
 Biomimetic oxidative dimerization of anodically generated stilbene
 radical cations: effect of aromatic substitution on product distribution
 and reaction pathways.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4528
_journal_page_last               4543
_journal_paper_doi               10.1021/jo500559r
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C32 H32 O5'
_chemical_formula_sum            'C32 H32 O5'
_chemical_formula_weight         496.58
_chemical_melting_point          120(2)
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.5972(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9058(5)
_cell_length_b                   9.7027(3)
_cell_length_c                   16.0143(4)
_cell_measurement_reflns_used    5165
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.37
_cell_volume                     2671.05(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
;  
SHELXL-97 (Sheldrick, 2008), enCIFer (Allen et al., 2004),
;
_computing_structure_refinement
;  
SHELXL97 (Sheldrick, 2008), Olex2 (Dolomanov & Puschmann, 2009)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.767
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16758
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1439 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.9476.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2904
_reflns_number_total             4387
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo500559r_si_002.cif
_cod_data_source_block           hfj2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '118-122' was changed to '120(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029384--4029417.cif.
;
_cod_database_code               4029398
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2A(0.041) H3A(0.04) H5A(0.044) H6A(0.042) H7A(0.037) H8A(0.034)
 H10A(0.037) H11A(0.039) H13A(0.05) H14A(0.046) H15A(0.071) H15B(0.071)
 H15C(0.071) H16A(0.078) H16B(0.078) H16C(0.078) H2B(0.049) H3B(0.048)
 H5B(0.04) H6B(0.038) H7B(0.038) H8B(0.036) H10B(0.045) H11B(0.051) H13B(0.04)
 H14B(0.037) H15D(0.075) H15E(0.075) H15F(0.075) H16D(0.141) H16E(0.141)
 H16F(0.141)
 Fixed X: H2A(0.3445) H3A(0.3741) H5A(0.3843) H6A(0.3574) H7A(0.3477)
 H8A(0.2116) H10A(0.1377) H11A(0.081) H13A(0.1989) H14A(0.2539) H15A(0.363)
 H15B(0.4211) H15C(0.452) H16A(0.0031) H16B(0.0267) H16C(0.0686) H2B(0.2163)
 H3B(0.2649) H5B(0.4803) H6B(0.4306) H7B(0.2622) H8B(0.2424) H10B(0.1343)
 H11B(0.0063) H13B(-0.0051) H14B(0.1232) H15D(0.5102) H15E(0.4865) H15F(0.4942)
 H16D(-0.1364) H16E(-0.1909) H16F(-0.1235)
 Fixed Y: H2A(0.5847) H3A(0.598) H5A(0.1855) H6A(0.1738) H7A(0.2871)
 H8A(0.4263) H10A(0.276) H11A(0.0644) H13A(-0.0951) H14A(0.1168) H15A(0.5727)
 H15B(0.5023) H15C(0.5657) H16A(-0.1227) H16B(-0.2784) H16C(-0.1679)
 H2B(0.5755) H3B(0.6258) H5B(0.6414) H6B(0.5914) H7B(0.6177) H8B(0.3481)
 H10B(0.6182) H11B(0.6714) H13B(0.3677) H14B(0.3141) H15D(0.619) H15E(0.7273)
 H15F(0.7724) H16D(0.3858) H16E(0.5114) H16F(0.4739)
 Fixed Z: H2A(0.5945) H3A(0.4686) H5A(0.4633) H6A(0.5908) H7A(0.7216)
 H8A(0.6028) H10A(0.4892) H11A(0.4353) H13A(0.6856) H14A(0.7389) H15A(0.3234)
 H15B(0.2895) H15C(0.3884) H16A(0.4279) H16B(0.4327) H16C(0.3979) H2B(0.8787)
 H3B(1.0326) H5B(1.0447) H6B(0.8889) H7B(0.7296) H8B(0.7859) H10B(0.6323)
 H11B(0.5949) H13B(0.7585) H14B(0.7946) H15D(1.202) H15E(1.2584) H15F(1.1686)
 H16D(0.6414) H16E(0.6336) H16F(0.7286)
;