#------------------------------------------------------------------------------
#$Date: 2017-08-05 21:49:44 +0300 (Sat, 05 Aug 2017) $
#$Revision: 199586 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032570.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_4032570
loop_
_publ_author_name
'Chong, Kam-Weng'
'Hong, Fong-Jiao'
'Thomas, Noel F.'
'Low, Yun-Yee'
'Kam, Toh-Seok'
_publ_section_title
;
 Electrochemically Mediated Oxidative Transformations of Substituted
 4-Methoxystilbenes: Effect of Ortho-Substituted Nucleophilic Groups.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6172
_journal_page_last               6191
_journal_paper_doi               10.1021/acs.joc.7b00753
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C42 H34 N4 O10 S2'
_chemical_formula_sum            'C42 H34 N4 O10 S2'
_chemical_formula_weight         818.85
_chemical_melting_point          307.0(10)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.4680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4911(2)
_cell_length_b                   13.2075(2)
_cell_length_c                   15.3206(3)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.20
_cell_measurement_theta_min      2.44
_cell_volume                     1914.66(6)
_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
'enCIFer (Allen, et. al., J. Applied Cryst., 37, 335-338, 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         2.442
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0436
_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/[σ²(Fo²)+(0.0419P)²+0.7753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2714
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00753_si_011.cif
_cod_data_source_block           ckw_01_pl
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '__computing_structure_refinement' replaced with
'_computing_structure_refinement'.

Automatic conversion script
Id: cif_correct_tags 4968 2017-02-21 14:55:21Z antanas 

The following automatic conversions were performed:

'_chemical_melting_point' value '306-308' was changed to '307.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032566--4032573.cif.
;
_cod_database_code               4032570
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1B S 0.55849(6) 0.42836(4) 0.26551(4) 0.03352(16) Uani 1 1 d . .
O1B O 0.8336(2) 0.02247(13) 0.54492(13) 0.0611(5) Uani 1 1 d . .
O2B O 0.44327(17) 0.35946(11) 0.25134(10) 0.0433(4) Uani 1 1 d . .
O3B O 0.68124(18) 0.41494(13) 0.21880(10) 0.0508(5) Uani 1 1 d . .
O4B O 0.25449(18) 0.48310(14) 0.33495(12) 0.0560(5) Uani 1 1 d . .
O5B O 0.1426(2) 0.52484(19) 0.21313(15) 0.0840(7) Uani 1 1 d . .
N1A N 0.60769(17) 0.42802(12) 0.37012(11) 0.0288(4) Uani 1 1 d . .
N2A N 0.2464(2) 0.52699(16) 0.26472(14) 0.0454(5) Uani 1 1 d . .
C1B C 0.6028(2) 0.27827(15) 0.46429(13) 0.0280(5) Uani 1 1 d . .
C2B C 0.7176(2) 0.28112(17) 0.52674(15) 0.0385(5) Uani 1 1 d . .
H2B H 0.7452 0.3427 0.5520 0.046 Uiso 1 1 calc R U
C3B C 0.7909(3) 0.19494(18) 0.55181(16) 0.0449(6) Uani 1 1 d . .
H3B H 0.8670 0.1988 0.5938 0.054 Uiso 1 1 calc R U
C4B C 0.7524(3) 0.10254(17) 0.51499(16) 0.0412(6) Uani 1 1 d . .
C5B C 0.6407(3) 0.09754(17) 0.45230(17) 0.0464(6) Uani 1 1 d . .
H5B H 0.6141 0.0358 0.4269 0.056 Uiso 1 1 calc R U
C6B C 0.5679(2) 0.18541(17) 0.42727(15) 0.0411(6) Uani 1 1 d . .
H6B H 0.4933 0.1816 0.3843 0.049 Uiso 1 1 calc R U
C7B C 0.5245(2) 0.37325(14) 0.43400(13) 0.0259(4) Uani 1 1 d . .
H7B H 0.4351 0.3523 0.4029 0.031 Uiso 1 1 calc R U
C8B C 0.4883(2) 0.44363(14) 0.51030(13) 0.0259(4) Uani 1 1 d . .
H8B H 0.5531 0.4263 0.5611 0.031 Uiso 1 1 calc R U
C9A C 0.3394(2) 0.42846(15) 0.53692(14) 0.0296(5) Uani 1 1 d . .
C10A C 0.7085(2) 0.50251(15) 0.40286(14) 0.0296(5) Uani 1 1 d . .
C11A C 0.8436(2) 0.50666(18) 0.37630(17) 0.0432(6) Uani 1 1 d . .
H11A H 0.8743 0.4584 0.3378 0.052 Uiso 1 1 calc R U
C12A C 0.9330(3) 0.5829(2) 0.40731(19) 0.0578(8) Uani 1 1 d . .
H12A H 1.0239 0.5870 0.3889 0.069 Uiso 1 1 calc R U
C13A C 0.8881(3) 0.6530(2) 0.46547(19) 0.0588(8) Uani 1 1 d . .
H13A H 0.9488 0.7044 0.4862 0.071 Uiso 1 1 calc R U
C14A C 0.2464(2) 0.35266(18) 0.50682(16) 0.0446(6) Uani 1 1 d . .
H14A H 0.2754 0.3049 0.4673 0.054 Uiso 1 1 calc R U
C15A C 0.5021(2) 0.55488(16) 0.24144(14) 0.0352(5) Uani 1 1 d . .
C16A C 0.3651(2) 0.59149(17) 0.24351(14) 0.0374(5) Uani 1 1 d . .
C17A C 0.3323(3) 0.6920(2) 0.22684(18) 0.0561(7) Uani 1 1 d . .
H17A H 0.2398 0.7149 0.2282 0.067 Uiso 1 1 calc R U
C18A C 0.4387(4) 0.7578(2) 0.2082(2) 0.0731(9) Uani 1 1 d . .
H18A H 0.4187 0.8260 0.1989 0.088 Uiso 1 1 calc R U
C19A C 0.5746(3) 0.7227(2) 0.2033(2) 0.0742(10) Uani 1 1 d . .
H19A H 0.6456 0.7669 0.1891 0.089 Uiso 1 1 calc R U
C20A C 0.6053(3) 0.6222(2) 0.21948(18) 0.0551(7) Uani 1 1 d . .
H20A H 0.6972 0.5992 0.2156 0.066 Uiso 1 1 calc R U
C21B C 0.8071(4) -0.07374(19) 0.50612(19) 0.0687(9) Uani 1 1 d . .
H21A H 0.7122 -0.0943 0.5148 0.103 Uiso 1 1 calc R U
H21B H 0.8724 -0.1223 0.5327 0.103 Uiso 1 1 calc R U
H21C H 0.8188 -0.0698 0.4445 0.103 Uiso 1 1 calc R U
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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3B S1B O2B 119.42(10) . .
O3B S1B N1A 108.05(10) . .
O2B S1B N1A 107.74(9) . .
O3B S1B C15A 104.85(11) . .
O2B S1B C15A 110.62(10) . .
N1A S1B C15A 105.28(10) . .
C4B O1B C21B 118.4(2) . .
C10A N1A C7B 118.40(16) . .
C10A N1A S1B 118.21(14) . .
C7B N1A S1B 121.29(13) . .
O5B N2A O4B 123.8(2) . .
O5B N2A C16A 117.8(2) . .
O4B N2A C16A 118.30(19) . .
C6B C1B C2B 117.12(19) . .
C6B C1B C7B 120.94(18) . .
C2B C1B C7B 121.85(18) . .
C3B C2B C1B 121.5(2) . .
C3B C2B H2B 119.3 . .
C1B C2B H2B 119.3 . .
C2B C3B C4B 120.4(2) . .
C2B C3B H3B 119.8 . .
C4B C3B H3B 119.8 . .
O1B C4B C5B 125.5(2) . .
O1B C4B C3B 115.0(2) . .
C5B C4B C3B 119.5(2) . .
C4B C5B C6B 119.5(2) . .
C4B C5B H5B 120.3 . .
C6B C5B H5B 120.3 . .
C1B C6B C5B 122.0(2) . .
C1B C6B H6B 119.0 . .
C5B C6B H6B 119.0 . .
N1A C7B C1B 109.32(16) . .
N1A C7B C8B 111.29(15) . .
C1B C7B C8B 113.44(16) . .
N1A C7B H7B 107.5 . .
C1B C7B H7B 107.5 . .
C8B C7B H7B 107.5 . .
C9A C8B C8B 109.6(2) . 3_666
C9A C8B C7B 112.91(16) . .
C8B C8B C7B 112.3(2) 3_666 .
C9A C8B H8B 107.2 . .
C8B C8B H8B 107.2 3_666 .
C7B C8B H8B 107.2 . .
C14A C9A C10A 117.24(19) . 3_666
C14A C9A C8B 126.01(19) . .
C10A C9A C8B 116.74(17) 3_666 .
C11A C10A C9A 121.9(2) . 3_666
C11A C10A N1A 122.35(19) . .
C9A C10A N1A 115.79(18) 3_666 .
C10A C11A C12A 119.4(2) . .
C10A C11A H11A 120.3 . .
C12A C11A H11A 120.3 . .
C13A C12A C11A 120.1(2) . .
C13A C12A H12A 119.9 . .
C11A C12A H12A 119.9 . .
C12A C13A C14A 120.3(2) . 3_666
C12A C13A H13A 119.9 . .
C14A C13A H13A 119.9 3_666 .
C13A C14A C9A 121.1(2) 3_666 .
C13A C14A H14A 119.5 3_666 .
C9A C14A H14A 119.5 . .
C20A C15A C16A 117.6(2) . .
C20A C15A S1B 116.49(18) . .
C16A C15A S1B 125.93(17) . .
C17A C16A C15A 121.8(2) . .
C17A C16A N2A 115.6(2) . .
C15A C16A N2A 122.6(2) . .
C18A C17A C16A 119.0(3) . .
C18A C17A H17A 120.5 . .
C16A C17A H17A 120.5 . .
C19A C18A C17A 120.2(3) . .
C19A C18A H18A 119.9 . .
C17A C18A H18A 119.9 . .
C20A C19A C18A 120.0(3) . .
C20A C19A H19A 120.0 . .
C18A C19A H19A 120.0 . .
C19A C20A C15A 121.3(3) . .
C19A C20A H20A 119.3 . .
C15A C20A H20A 119.3 . .
O1B C21B H21A 109.5 . .
O1B C21B H21B 109.5 . .
H21A C21B H21B 109.5 . .
O1B C21B H21C 109.5 . .
H21A C21B H21C 109.5 . .
H21B C21B H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1B O3B 1.4252(17) .
S1B O2B 1.4263(16) .
S1B N1A 1.6340(17) .
S1B C15A 1.784(2) .
O1B C4B 1.367(3) .
O1B C21B 1.417(3) .
O4B N2A 1.219(2) .
O5B N2A 1.214(2) .
N1A C10A 1.435(2) .
N1A C7B 1.492(2) .
N2A C16A 1.469(3) .
C1B C6B 1.381(3) .
C1B C2B 1.394(3) .
C1B C7B 1.513(3) .
C2B C3B 1.373(3) .
C2B H2B 0.9300 .
C3B C4B 1.382(3) .
C3B H3B 0.9300 .
C4B C5B 1.376(3) .
C5B C6B 1.389(3) .
C5B H5B 0.9300 .
C6B H6B 0.9300 .
C7B C8B 1.553(3) .
C7B H7B 0.9800 .
C8B C9A 1.514(3) .
C8B C8B 1.542(4) 3_666
C8B H8B 0.9800 .
C9A C14A 1.390(3) .
C9A C10A 1.398(3) 3_666
C10A C11A 1.376(3) .
C10A C9A 1.398(3) 3_666
C11A C12A 1.377(3) .
C11A H11A 0.9300 .
C12A C13A 1.375(4) .
C12A H12A 0.9300 .
C13A C14A 1.379(3) 3_666
C13A H13A 0.9300 .
C14A C13A 1.379(3) 3_666
C14A H14A 0.9300 .
C15A C20A 1.384(3) .
C15A C16A 1.391(3) .
C16A C17A 1.382(3) .
C17A C18A 1.379(4) .
C17A H17A 0.9300 .
C18A C19A 1.378(4) .
C18A H18A 0.9300 .
C19A C20A 1.377(4) .
C19A H19A 0.9300 .
C20A H20A 0.9300 .
C21B H21A 0.9600 .
C21B H21B 0.9600 .
C21B H21C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3B S1B N1A C10A 58.76(17) . .
O2B S1B N1A C10A -170.94(15) . .
C15A S1B N1A C10A -52.86(17) . .
O3B S1B N1A C7B -137.98(15) . .
O2B S1B N1A C7B -7.68(17) . .
C15A S1B N1A C7B 110.41(16) . .
C6B C1B C2B C3B -1.4(3) . .
C7B C1B C2B C3B -177.9(2) . .
C1B C2B C3B C4B 0.3(4) . .
C21B O1B C4B C5B 3.3(4) . .
C21B O1B C4B C3B -175.7(2) . .
C2B C3B C4B O1B 179.7(2) . .
C2B C3B C4B C5B 0.6(4) . .
O1B C4B C5B C6B -179.3(2) . .
C3B C4B C5B C6B -0.3(4) . .
C2B C1B C6B C5B 1.7(3) . .
C7B C1B C6B C5B 178.2(2) . .
C4B C5B C6B C1B -0.9(4) . .
C10A N1A C7B C1B -90.4(2) . .
S1B N1A C7B C1B 106.38(17) . .
C10A N1A C7B C8B 35.7(2) . .
S1B N1A C7B C8B -127.53(15) . .
C6B C1B C7B N1A -98.1(2) . .
C2B C1B C7B N1A 78.3(2) . .
C6B C1B C7B C8B 137.1(2) . .
C2B C1B C7B C8B -46.6(3) . .
N1A C7B C8B C9A 139.47(16) . .
C1B C7B C8B C9A -96.8(2) . .
N1A C7B C8B C8B 14.9(3) . 3_666
C1B C7B C8B C8B 138.7(2) . 3_666
C8B C8B C9A C14A 133.9(2) 3_666 .
C7B C8B C9A C14A 7.9(3) . .
C8B C8B C9A C10A -45.8(3) 3_666 3_666
C7B C8B C9A C10A -171.90(18) . 3_666
C7B N1A C10A C11A 133.5(2) . .
S1B N1A C10A C11A -62.7(2) . .
C7B N1A C10A C9A -47.0(2) . 3_666
S1B N1A C10A C9A 116.73(18) . 3_666
C9A C10A C11A C12A -2.3(4) 3_666 .
N1A C10A C11A C12A 177.1(2) . .
C10A C11A C12A C13A 1.2(4) . .
C11A C12A C13A C14A 0.1(5) . 3_666
C10A C9A C14A C13A 0.9(4) 3_666 3_666
C8B C9A C14A C13A -178.9(2) . 3_666
O3B S1B C15A C20A -25.9(2) . .
O2B S1B C15A C20A -155.92(19) . .
N1A S1B C15A C20A 88.0(2) . .
O3B S1B C15A C16A 154.6(2) . .
O2B S1B C15A C16A 24.6(2) . .
N1A S1B C15A C16A -91.5(2) . .
C20A C15A C16A C17A -1.8(3) . .
S1B C15A C16A C17A 177.62(19) . .
C20A C15A C16A N2A 179.2(2) . .
S1B C15A C16A N2A -1.4(3) . .
O5B N2A C16A C17A 54.9(3) . .
O4B N2A C16A C17A -121.3(2) . .
O5B N2A C16A C15A -126.0(3) . .
O4B N2A C16A C15A 57.8(3) . .
C15A C16A C17A C18A -0.4(4) . .
N2A C16A C17A C18A 178.7(2) . .
C16A C17A C18A C19A 2.3(5) . .
C17A C18A C19A C20A -1.8(5) . .
C18A C19A C20A C15A -0.5(5) . .
C16A C15A C20A C19A 2.3(4) . .
S1B C15A C20A C19A -177.2(2) . .
