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_4029390
_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         'C34 H38 N2 O3'
_chemical_formula_sum            'C34 H38 N2 O3'
_chemical_formula_weight         522.66
_chemical_melting_point          178.0(10)
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.8256(10)
_cell_length_b                   10.1693(4)
_cell_length_c                   25.5637(11)
_cell_measurement_reflns_used    2914
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.35
_cell_volume                     5673.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2248
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            44616
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_min         1.593
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_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          0.1766
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2574
_reflns_number_total             5866
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo500559r_si_019.cif
_cod_data_source_block           HFJ1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '177-179' was changed to '178.0(10)'
- 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               4029390
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7'(0.043) H6'(0.047) H6(0.05) H7(0.045) H10(0.054) H5'(0.051)
 H5(0.056) H2(0.05) H11(0.053) H8(0.051) H3(0.057) H13(0.064) H8'(0.055)
 H14(0.061) H2'(0.07) H13'(0.077) H11'(0.066) H10'(0.065) H14'(0.073)
 H17A(0.108) H17B(0.108) H17C(0.108) H16A(0.108) H16B(0.108) H16C(0.108)
 H3'(0.083) H15A(0.145) H15B(0.145) H15C(0.145) H16D(0.137) H16E(0.137)
 H16F(0.137) H15D(0.127) H15E(0.127) H15F(0.127) H17D(0.161) H17E(0.161)
 H17F(0.161)
 Fixed X: H7'(0.1101) H6'(0.0379) H6(0.0714) H7(0.1871) H10(0.303) H5'(-
 0.0043) H5(-0.003) H2(0.1358) H11(0.3755) H8(0.1789) H3(0.0604) H13(0.289)
 H8'(0.2253) H14(0.22) H2'(0.1785) H13'(0.1711) H11'(0.1845) H10'(0.1958)
 H14'(0.1871) H17A(0.3422) H17B(0.4085) H17C(0.3989) H16A(0.4593) H16B(0.4549)
 H16C(0.4219) H3'(0.1381) H15A(-0.0066) H15B(-0.0235) H15C(-0.0456)
 H16D(0.0915) H16E(0.136) H16F(0.1465) H15D(-0.0812) H15E(-0.0843) H15F(-
 0.0306) H17D(0.202) H17E(0.1687) H17F(0.1304)
 Fixed Y: H7'(0.1423) H6'(0.0549) H6(0.189) H7(-0.0401) H10(0.0049) H5'(-
 0.1126) H5(0.1453) H2(-0.1761) H11(-0.0497) H8(0.229) H3(-0.2212) H13(0.1787)
 H8'(0.0467) H14(0.239) H2'(-0.174) H13'(0.1691) H11'(0.501) H10'(0.3808)
 H14'(0.0511) H17A(0.092) H17B(0.038) H17C(0.1691) H16A(-0.006) H16B(-0.0897)
 H16C(-0.1377) H3'(-0.3399) H15A(-0.267) H15B(-0.4146) H15C(-0.3055)
 H16D(0.3635) H16E(0.4193) H16F(0.2779) H15D(0.0637) H15E(-0.0179) H15F(0.082)
 H17D(0.5932) H17E(0.597) H17F(0.5851)
 Fixed Z: H7'(0.3693) H6'(0.4268) H6(0.2766) H7(0.3177) H10(0.3093)
 H5'(0.4763) H5(0.2157) H2(0.2614) H11(0.2482) H8(0.2912) H3(0.2015)
 H13(0.1441) H8'(0.4043) H14(0.2073) H2'(0.3886) H13'(0.5682) H11'(0.4874)
 H10'(0.411) H14'(0.4936) H17A(0.0858) H17B(0.0763) H17C(0.1075) H16A(0.1844)
 H16B(0.133) H16C(0.184) H3'(0.4403) H15A(0.5466) H15B(0.5365) H15C(0.4975)
 H16D(0.6114) H16E(0.6541) H16F(0.6314) H15D(0.1696) H15E(0.1176) H15F(0.1267)
 H17D(0.5604) H17E(0.6147) H17F(0.563)
;
_shelx_res_checksum              10307
_shelx_hkl_checksum              39511