#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/94/4029417.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029417
loop_
_publ_author_name
'Hong, Fong-Jiao'
'Low, Yun-Yee'
'Chong, Kam-Weng'
'Thomas, Noel F.'
'Kam, Toh-Seok'
_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 H31 N O'
_chemical_formula_sum            'C32 H31 N O'
_chemical_formula_weight         445.58
_chemical_melting_point          233(2)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.144(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.173(8)
_cell_length_b                   25.204(19)
_cell_length_c                   9.160(7)
_cell_measurement_reflns_used    304
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.45
_cell_measurement_theta_min      2.41
_cell_volume                     2522(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2686
_diffrn_reflns_av_sigmaI/netI    0.4174
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.3569
_refine_ls_R_factor_gt           0.0914
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.2941
_reflns_number_gt                1256
_reflns_number_total             5273
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo500559r_si_028.cif
_cod_data_source_block           hfj_5111_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '231-235' was changed to '233(2)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

 Adding full bibliography for 4029384--4029417.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1A C 0.4394(7) 0.1874(3) 0.8319(8) 0.0382(18) Uani 1 1 d .
C2A C 0.5104(7) 0.2246(3) 0.7757(8) 0.048(2) Uani 1 1 d .
H2A H 0.4755 0.2450 0.6929 0.058 Uiso 1 1 calc R
C3A C 0.6342(7) 0.2315(3) 0.8434(9) 0.053(2) Uani 1 1 d .
H3A H 0.6802 0.2569 0.8060 0.063 Uiso 1 1 calc R
C4A C 0.6892(6) 0.2010(3) 0.9652(8) 0.0414(19) Uani 1 1 d .
C5A C 0.6155(7) 0.1630(3) 1.0150(8) 0.0435(19) Uani 1 1 d .
H5A H 0.6509 0.1420 1.0961 0.052 Uiso 1 1 calc R
C6A C 0.4933(7) 0.1548(3) 0.9513(8) 0.0409(19) Uani 1 1 d .
C7A C 0.3051(6) 0.1821(2) 0.7564(7) 0.0380(18) Uani 1 1 d .
H7A H 0.2979 0.1881 0.6492 0.046 Uiso 1 1 calc R
C8A C 0.2534(6) 0.1264(3) 0.7770(7) 0.0355(18) Uani 1 1 d .
H8A H 0.3006 0.1016 0.7288 0.043 Uiso 1 1 calc R
C9A C 0.1216(7) 0.1203(3) 0.6962(8) 0.0428(19) Uani 1 1 d .
C10A C 0.0253(7) 0.1446(3) 0.7469(9) 0.052(2) Uani 1 1 d .
H10A H 0.0412 0.1639 0.8355 0.062 Uiso 1 1 calc R
C11A C -0.0948(8) 0.1400(3) 0.6646(10) 0.064(2) Uani 1 1 d .
H11A H -0.1583 0.1561 0.6996 0.076 Uiso 1 1 calc R
C12A C -0.1203(8) 0.1120(4) 0.5319(11) 0.070(3) Uani 1 1 d .
H12A H -0.2002 0.1099 0.4768 0.084 Uiso 1 1 calc R
C13A C -0.0264(8) 0.0873(3) 0.4818(9) 0.066(3) Uani 1 1 d .
H13A H -0.0437 0.0676 0.3939 0.080 Uiso 1 1 calc R
C14A C 0.0940(7) 0.0912(3) 0.5613(8) 0.051(2) Uani 1 1 d .
H14A H 0.1565 0.0747 0.5255 0.061 Uiso 1 1 calc R
C15A C 0.8214(6) 0.2075(3) 1.0373(9) 0.066(3) Uani 1 1 d .
H15A H 0.8657 0.2195 0.9644 0.099 Uiso 1 1 calc R
H15B H 0.8540 0.1740 1.0773 0.099 Uiso 1 1 calc R
H15C H 0.8294 0.2330 1.1165 0.099 Uiso 1 1 calc R
C16A C 0.1817(6) 0.2658(3) 0.7325(8) 0.0410(19) Uani 1 1 d .
C17A C 0.1179(6) 0.3051(3) 0.8126(7) 0.051(2) Uani 1 1 d .
H17A H 0.1760 0.3308 0.8621 0.076 Uiso 1 1 calc R
H17B H 0.0822 0.2869 0.8851 0.076 Uiso 1 1 calc R
H17C H 0.0548 0.3227 0.7420 0.076 Uiso 1 1 calc R
C1B C 0.4597(6) 0.1001(3) 1.1721(8) 0.0393(19) Uani 1 1 d .
C2B C 0.4377(6) 0.1389(3) 1.2715(8) 0.0437(19) Uani 1 1 d .
H2B H 0.3964 0.1697 1.2344 0.052 Uiso 1 1 calc R
C3B C 0.4760(7) 0.1327(3) 1.4246(8) 0.046(2) Uani 1 1 d .
H3B H 0.4594 0.1590 1.4885 0.055 Uiso 1 1 calc R
C4B C 0.5393(6) 0.0872(3) 1.4835(7) 0.0403(19) Uani 1 1 d .
C5B C 0.5605(6) 0.0482(3) 1.3847(8) 0.0435(19) Uani 1 1 d .
H5B H 0.6016 0.0174 1.4220 0.052 Uiso 1 1 calc R
C6B C 0.5213(6) 0.0544(3) 1.2315(8) 0.0428(19) Uani 1 1 d .
H6B H 0.5364 0.0276 1.1678 0.051 Uiso 1 1 calc R
C7B C 0.4227(6) 0.1088(3) 1.0028(7) 0.0385(18) Uani 1 1 d .
H7B H 0.4491 0.0768 0.9573 0.046 Uiso 1 1 calc R
C8B C 0.2832(6) 0.1117(3) 0.9460(7) 0.0381(18) Uani 1 1 d .
H8B H 0.2509 0.1397 1.0013 0.046 Uiso 1 1 calc R
C9B C 0.2283(6) 0.0586(3) 0.9796(8) 0.0377(18) Uani 1 1 d .
C10B C 0.2299(7) 0.0143(3) 0.8888(8) 0.048(2) Uani 1 1 d .
H10B H 0.2586 0.0176 0.8010 0.058 Uiso 1 1 calc R
C11B C 0.1895(7) -0.0344(3) 0.9276(9) 0.056(2) Uani 1 1 d .
H11B H 0.1928 -0.0637 0.8668 0.068 Uiso 1 1 calc R
C12B C 0.1445(7) -0.0399(3) 1.0548(11) 0.061(3) Uani 1 1 d .
H12B H 0.1176 -0.0729 1.0798 0.073 Uiso 1 1 calc R
C13B C 0.1387(7) 0.0035(3) 1.1468(9) 0.057(2) Uani 1 1 d .
H13B H 0.1079 0.0000 1.2331 0.068 Uiso 1 1 calc R
C14B C 0.1809(6) 0.0526(3) 1.1057(8) 0.049(2) Uani 1 1 d .
H14B H 0.1766 0.0821 1.1656 0.058 Uiso 1 1 calc R
C15B C 0.5855(6) 0.0807(3) 1.6507(7) 0.053(2) Uani 1 1 d .
H15D H 0.5199 0.0686 1.6951 0.079 Uiso 1 1 calc R
H15E H 0.6152 0.1142 1.6937 0.079 Uiso 1 1 calc R
H15F H 0.6508 0.0552 1.6690 0.079 Uiso 1 1 calc R
N7A N 0.2368(5) 0.2244(2) 0.8137(6) 0.0392(15) Uani 1 1 d .
H7A1 H 0.2315 0.2227 0.9059 0.047 Uiso 1 1 calc R
O16A O 0.1851(5) 0.27182(18) 0.5978(5) 0.0559(15) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2A C1A C6A 120.0(7)
C2A C1A C7A 118.3(7)
C6A C1A C7A 121.7(6)
C1A C2A C3A 120.3(7)
C1A C2A H2A 119.8
C3A C2A H2A 119.8
C4A C3A C2A 121.0(7)
C4A C3A H3A 119.5
C2A C3A H3A 119.5
C3A C4A C5A 116.7(7)
C3A C4A C15A 121.6(7)
C5A C4A C15A 121.6(7)
C6A C5A C4A 124.1(7)
C6A C5A H5A 117.9
C4A C5A H5A 117.9
C5A C6A C1A 117.8(7)
C5A C6A C7B 120.7(7)
C1A C6A C7B 121.4(6)
N7A C7A C1A 108.1(5)
N7A C7A C8A 112.4(5)
C1A C7A C8A 112.4(6)
N7A C7A H7A 107.9
C1A C7A H7A 107.9
C8A C7A H7A 107.9
C9A C8A C7A 112.6(6)
C9A C8A C8B 116.5(5)
C7A C8A C8B 109.2(5)
C9A C8A H8A 105.9
C7A C8A H8A 105.9
C8B C8A H8A 105.9
C10A C9A C14A 118.4(7)
C10A C9A C8A 122.0(7)
C14A C9A C8A 119.5(7)
C11A C10A C9A 120.1(8)
C11A C10A H10A 119.9
C9A C10A H10A 119.9
C12A C11A C10A 120.9(9)
C12A C11A H11A 119.6
C10A C11A H11A 119.6
C13A C12A C11A 119.5(9)
C13A C12A H12A 120.3
C11A C12A H12A 120.3
C12A C13A C14A 120.8(8)
C12A C13A H13A 119.6
C14A C13A H13A 119.6
C13A C14A C9A 120.3(8)
C13A C14A H14A 119.9
C9A C14A H14A 119.9
C4A C15A H15A 109.5
C4A C15A H15B 109.5
H15A C15A H15B 109.5
C4A C15A H15C 109.5
H15A C15A H15C 109.5
H15B C15A H15C 109.5
O16A C16A N7A 122.2(7)
O16A C16A C17A 121.2(7)
N7A C16A C17A 116.6(6)
C16A C17A H17A 109.5
C16A C17A H17B 109.5
H17A C17A H17B 109.5
C16A C17A H17C 109.5
H17A C17A H17C 109.5
H17B C17A H17C 109.5
C6B C1B C2B 117.8(7)
C6B C1B C7B 121.2(6)
C2B C1B C7B 120.9(6)
C3B C2B C1B 121.4(7)
C3B C2B H2B 119.3
C1B C2B H2B 119.3
C2B C3B C4B 120.6(6)
C2B C3B H3B 119.7
C4B C3B H3B 119.7
C5B C4B C3B 118.1(6)
C5B C4B C15B 120.8(7)
C3B C4B C15B 121.1(6)
C6B C5B C4B 121.2(7)
C6B C5B H5B 119.4
C4B C5B H5B 119.4
C5B C6B C1B 120.8(7)
C5B C6B H6B 119.6
C1B C6B H6B 119.6
C6A C7B C1B 111.9(5)
C6A C7B C8B 114.2(6)
C1B C7B C8B 112.8(6)
C6A C7B H7B 105.7
C1B C7B H7B 105.7
C8B C7B H7B 105.7
C9B C8B C7B 108.1(5)
C9B C8B C8A 113.3(6)
C7B C8B C8A 109.7(5)
C9B C8B H8B 108.5
C7B C8B H8B 108.5
C8A C8B H8B 108.5
C14B C9B C10B 117.9(7)
C14B C9B C8B 120.4(7)
C10B C9B C8B 121.6(7)
C11B C10B C9B 120.8(8)
C11B C10B H10B 119.6
C9B C10B H10B 119.6
C12B C11B C10B 120.5(8)
C12B C11B H11B 119.7
C10B C11B H11B 119.7
C11B C12B C13B 120.5(8)
C11B C12B H12B 119.7
C13B C12B H12B 119.7
C12B C13B C14B 118.0(8)
C12B C13B H13B 121.0
C14B C13B H13B 121.0
C9B C14B C13B 122.1(8)
C9B C14B H14B 119.0
C13B C14B H14B 119.0
C4B C15B H15D 109.5
C4B C15B H15E 109.5
H15D C15B H15E 109.5
C4B C15B H15F 109.5
H15D C15B H15F 109.5
H15E C15B H15F 109.5
C16A N7A C7A 125.0(6)
C16A N7A H7A1 117.5
C7A N7A H7A1 117.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1A C2A 1.396(9)
C1A C6A 1.399(9)
C1A C7A 1.521(9)
C2A C3A 1.403(10)
C2A H2A 0.9300
C3A C4A 1.388(9)
C3A H3A 0.9300
C4A C5A 1.401(9)
C4A C15A 1.494(9)
C5A C6A 1.383(9)
C5A H5A 0.9300
C6A C7B 1.531(9)
C7A N7A 1.470(8)
C7A C8A 1.545(8)
C7A H7A 0.9800
C8A C9A 1.511(9)
C8A C8B 1.557(8)
C8A H8A 0.9800
C9A C10A 1.401(9)
C9A C14A 1.413(9)
C10A C11A 1.399(10)
C10A H10A 0.9300
C11A C12A 1.383(11)
C11A H11A 0.9300
C12A C13A 1.380(11)
C12A H12A 0.9300
C13A C14A 1.392(10)
C13A H13A 0.9300
C14A H14A 0.9300
C15A H15A 0.9600
C15A H15B 0.9600
C15A H15C 0.9600
C16A O16A 1.251(7)
C16A N7A 1.351(8)
C16A C17A 1.500(9)
C17A H17A 0.9600
C17A H17B 0.9600
C17A H17C 0.9600
C1B C6B 1.393(9)
C1B C2B 1.394(9)
C1B C7B 1.535(9)
C2B C3B 1.386(9)
C2B H2B 0.9300
C3B C4B 1.394(9)
C3B H3B 0.9300
C4B C5B 1.390(9)
C4B C15B 1.519(9)
C5B C6B 1.388(9)
C5B H5B 0.9300
C6B H6B 0.9300
C7B C8B 1.537(9)
C7B H7B 0.9800
C8B C9B 1.531(9)
C8B H8B 0.9800
C9B C14B 1.377(9)
C9B C10B 1.395(9)
C10B C11B 1.379(9)
C10B H10B 0.9300
C11B C12B 1.370(10)
C11B H11B 0.9300
C12B C13B 1.390(11)
C12B H12B 0.9300
C13B C14B 1.405(9)
C13B H13B 0.9300
C14B H14B 0.9300
C15B H15D 0.9600
C15B H15E 0.9600
C15B H15F 0.9600
N7A H7A1 0.8600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139093412
