#------------------------------------------------------------------------------
#$Date: 2017-08-05 21:49:44 +0300 (Sat, 05 Aug 2017) $
#$Revision: 199586 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032567.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_4032567
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         'C36 H36 N2 O8'
_chemical_formula_sum            'C36 H36 N2 O8'
_chemical_formula_weight         624.67
_chemical_melting_point          252.0(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                 100.576(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2055(3)
_cell_length_b                   8.1914(2)
_cell_length_c                   20.5255(5)
_cell_measurement_reflns_used    3215
_cell_measurement_temperature    144(1)
_cell_measurement_theta_max      73.5130
_cell_measurement_theta_min      5.8100
_cell_volume                     1521.45(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      144(1)
_diffrn_detector_area_resol_mean 5.2020
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5644
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.949
_diffrn_reflns_theta_min         4.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0439
_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)+(0.0704P)²+0.3849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2609
_reflns_number_total             2970
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00753_si_013.cif
_cod_data_source_block           exp_6093
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '251-253' was changed to '252.0(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_original_cell_volume        1521.46(7)
_cod_database_code               4032567
_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
C15 C 1.08088(14) 0.53152(16) 0.00730(6) 0.0232(3) Uani 1 1 d . .
H15 H 1.0784 0.6469 -0.0055 0.028 Uiso 1 1 calc R U
C22 C 0.7753(2) 0.3702(2) 0.27249(7) 0.0423(4) Uani 1 1 d . .
H22A H 0.8696 0.3510 0.2603 0.063 Uiso 1 1 calc R U
H22B H 0.7779 0.3339 0.3172 0.063 Uiso 1 1 calc R U
H22C H 0.7533 0.4848 0.2695 0.063 Uiso 1 1 calc R U
C1A C 0.72814(15) 0.43813(17) 0.06702(6) 0.0241(3) Uani 1 1 d . .
C2A C 0.73696(15) 0.42535(17) 0.13566(6) 0.0254(3) Uani 1 1 d . .
H2A H 0.7969 0.4970 0.1638 0.030 Uiso 1 1 calc R U
C3A C 0.65713(15) 0.30685(17) 0.16217(6) 0.0254(3) Uani 1 1 d . .
C4A C 0.56219(15) 0.20119(17) 0.12061(6) 0.0256(3) Uani 1 1 d . .
C5A C 0.55106(16) 0.21623(18) 0.05238(7) 0.0271(3) Uani 1 1 d . .
H5A H 0.4878 0.1479 0.0241 0.032 Uiso 1 1 calc R U
C6A C 0.63391(16) 0.33276(18) 0.02621(6) 0.0271(3) Uani 1 1 d . .
H6A H 0.6262 0.3404 -0.0195 0.032 Uiso 1 1 calc R U
C7A C 0.82077(15) 0.55931(17) 0.03581(6) 0.0228(3) Uani 1 1 d . .
H7A H 0.7523 0.6295 0.0060 0.027 Uiso 1 1 calc R U
C9A C 1.04678(15) 0.59929(16) 0.12027(6) 0.0239(3) Uani 1 1 d . .
C10A C 1.13790(15) 0.52390(17) 0.08166(6) 0.0243(3) Uani 1 1 d . .
C11A C 1.26867(17) 0.45374(19) 0.11390(7) 0.0304(3) Uani 1 1 d . .
H11A H 1.3310 0.4028 0.0893 0.036 Uiso 1 1 calc R U
C12A C 1.30771(17) 0.4588(2) 0.18281(7) 0.0344(4) Uani 1 1 d . .
H12A H 1.3954 0.4109 0.2039 0.041 Uiso 1 1 calc R U
C13A C 1.21574(18) 0.5352(2) 0.21995(7) 0.0324(3) Uani 1 1 d . .
H13A H 1.2427 0.5393 0.2659 0.039 Uiso 1 1 calc R U
C14A C 1.08421(16) 0.60512(18) 0.18911(7) 0.0281(3) Uani 1 1 d . .
H14A H 1.0218 0.6552 0.2139 0.034 Uiso 1 1 calc R U
C15A C 0.88775(16) 0.83021(18) 0.07942(7) 0.0290(3) Uani 1 1 d . .
C16A C 0.9813(3) 1.0891(2) 0.11420(12) 0.0590(6) Uani 1 1 d . .
H16A H 1.0088 1.1261 0.0738 0.089 Uiso 1 1 calc R U
H16B H 1.0449 1.1382 0.1513 0.089 Uiso 1 1 calc R U
H16C H 0.8807 1.1195 0.1146 0.089 Uiso 1 1 calc R U
C17A C 0.4063(2) -0.0324(2) 0.11071(7) 0.0383(4) Uani 1 1 d . .
H17A H 0.3311 0.0169 0.0780 0.057 Uiso 1 1 calc R U
H17B H 0.3612 -0.1055 0.1377 0.057 Uiso 1 1 calc R U
H17C H 0.4734 -0.0922 0.0890 0.057 Uiso 1 1 calc R U
N1A N 0.91129(13) 0.66598(14) 0.08506(5) 0.0238(3) Uani 1 1 d . .
O3A O 0.66401(12) 0.28258(13) 0.22882(4) 0.0301(3) Uani 1 1 d . .
O4A O 0.48517(12) 0.09179(13) 0.15140(5) 0.0297(3) Uani 1 1 d . .
O15A O 0.78243(14) 0.89287(14) 0.04410(6) 0.0465(3) Uani 1 1 d . .
O16A O 0.99525(13) 0.91452(13) 0.11854(5) 0.0350(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10A C15 C15 108.79(13) . 3_765
C10A C15 C7A 114.76(11) . 3_765
C15 C15 C7A 111.51(13) 3_765 3_765
C10A C15 H15 107.1 . .
C15 C15 H15 107.1 3_765 .
C7A C15 H15 107.1 3_765 .
O3A C22 H22A 109.5 . .
O3A C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
O3A C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C6A C1A C2A 118.32(12) . .
C6A C1A C7A 119.11(11) . .
C2A C1A C7A 122.55(12) . .
C3A C2A C1A 120.66(13) . .
C3A C2A H2A 119.7 . .
C1A C2A H2A 119.7 . .
O3A C3A C2A 124.16(12) . .
O3A C3A C4A 115.24(12) . .
C2A C3A C4A 120.60(12) . .
O4A C4A C5A 125.09(13) . .
O4A C4A C3A 116.20(11) . .
C5A C4A C3A 118.70(13) . .
C6A C5A C4A 120.38(13) . .
C6A C5A H5A 119.8 . .
C4A C5A H5A 119.8 . .
C5A C6A C1A 121.30(12) . .
C5A C6A H6A 119.3 . .
C1A C6A H6A 119.3 . .
N1A C7A C1A 112.80(10) . .
N1A C7A C15 110.90(10) . 3_765
C1A C7A C15 110.75(11) . 3_765
N1A C7A H7A 107.4 . .
C1A C7A H7A 107.4 . .
C15 C7A H7A 107.4 3_765 .
C14A C9A C10A 121.84(13) . .
C14A C9A N1A 122.01(12) . .
C10A C9A N1A 116.12(11) . .
C11A C10A C9A 118.08(12) . .
C11A C10A C15 127.21(12) . .
C9A C10A C15 114.70(12) . .
C10A C11A C12A 120.73(13) . .
C10A C11A H11A 119.6 . .
C12A C11A H11A 119.6 . .
C13A C12A C11A 120.05(14) . .
C13A C12A H12A 120.0 . .
C11A C12A H12A 120.0 . .
C14A C13A C12A 120.42(13) . .
C14A C13A H13A 119.8 . .
C12A C13A H13A 119.8 . .
C13A C14A C9A 118.88(13) . .
C13A C14A H14A 120.6 . .
C9A C14A H14A 120.6 . .
O15A C15A O16A 124.02(13) . .
O15A C15A N1A 124.41(14) . .
O16A C15A N1A 111.57(12) . .
O16A C16A H16A 109.5 . .
O16A C16A H16B 109.5 . .
H16A C16A H16B 109.5 . .
O16A C16A H16C 109.5 . .
H16A C16A H16C 109.5 . .
H16B C16A H16C 109.5 . .
O4A C17A H17A 109.5 . .
O4A C17A H17B 109.5 . .
H17A C17A H17B 109.5 . .
O4A C17A H17C 109.5 . .
H17A C17A H17C 109.5 . .
H17B C17A H17C 109.5 . .
C15A N1A C9A 121.99(12) . .
C15A N1A C7A 117.75(11) . .
C9A N1A C7A 116.82(11) . .
C3A O3A C22 116.76(11) . .
C4A O4A C17A 116.61(11) . .
C15A O16A C16A 115.22(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C15 C10A 1.5214(16) .
C15 C15 1.553(3) 3_765
C15 C7A 1.5652(17) 3_765
C15 H15 0.9800 .
C22 O3A 1.4253(18) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C1A C6A 1.3901(19) .
C1A C2A 1.4002(17) .
C1A C7A 1.5242(19) .
C2A C3A 1.387(2) .
C2A H2A 0.9300 .
C3A O3A 1.3723(15) .
C3A C4A 1.402(2) .
C4A O4A 1.3674(17) .
C4A C5A 1.3907(18) .
C5A C6A 1.390(2) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
C7A N1A 1.4733(17) .
C7A C15 1.5653(17) 3_765
C7A H7A 0.9800 .
C9A C14A 1.3924(18) .
C9A C10A 1.3989(19) .
C9A N1A 1.4302(17) .
C10A C11A 1.387(2) .
C11A C12A 1.3946(19) .
C11A H11A 0.9300 .
C12A C13A 1.388(2) .
C12A H12A 0.9300 .
C13A C14A 1.383(2) .
C13A H13A 0.9300 .
C14A H14A 0.9300 .
C15A O15A 1.2128(18) .
C15A O16A 1.3451(17) .
C15A N1A 1.3642(19) .
C16A O16A 1.437(2) .
C16A H16A 0.9600 .
C16A H16B 0.9600 .
C16A H16C 0.9600 .
C17A O4A 1.4276(18) .
C17A H17A 0.9600 .
C17A H17B 0.9600 .
C17A H17C 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
C6A C1A C2A C3A 2.1(2) . .
C7A C1A C2A C3A -176.17(12) . .
C1A C2A C3A O3A 177.49(13) . .
C1A C2A C3A C4A -2.2(2) . .
O3A C3A C4A O4A 2.14(19) . .
C2A C3A C4A O4A -178.16(12) . .
O3A C3A C4A C5A -178.92(12) . .
C2A C3A C4A C5A 0.8(2) . .
O4A C4A C5A C6A 179.53(13) . .
C3A C4A C5A C6A 0.7(2) . .
C4A C5A C6A C1A -0.8(2) . .
C2A C1A C6A C5A -0.6(2) . .
C7A C1A C6A C5A 177.71(13) . .
C6A C1A C7A N1A 178.16(12) . .
C2A C1A C7A N1A -3.63(18) . .
C6A C1A C7A C15 -56.88(16) . 3_765
C2A C1A C7A C15 121.33(13) . 3_765
C14A C9A C10A C11A 0.0(2) . .
N1A C9A C10A C11A -178.35(13) . .
C14A C9A C10A C15 -179.04(12) . .
N1A C9A C10A C15 2.59(18) . .
C15 C15 C10A C11A 129.26(16) 3_765 .
C7A C15 C10A C11A 3.6(2) 3_765 .
C15 C15 C10A C9A -51.79(18) 3_765 .
C7A C15 C10A C9A -177.47(11) 3_765 .
C9A C10A C11A C12A -0.1(2) . .
C15 C10A C11A C12A 178.85(14) . .
C10A C11A C12A C13A -0.3(3) . .
C11A C12A C13A C14A 0.7(3) . .
C12A C13A C14A C9A -0.8(2) . .
C10A C9A C14A C13A 0.4(2) . .
N1A C9A C14A C13A 178.69(13) . .
O15A C15A N1A C9A 171.27(14) . .
O16A C15A N1A C9A -9.40(18) . .
O15A C15A N1A C7A 12.9(2) . .
O16A C15A N1A C7A -167.80(11) . .
C14A C9A N1A C15A 71.96(18) . .
C10A C9A N1A C15A -109.68(15) . .
C14A C9A N1A C7A -129.46(13) . .
C10A C9A N1A C7A 48.90(16) . .
C1A C7A N1A C15A -119.76(13) . .
C15 C7A N1A C15A 115.35(13) 3_765 .
C1A C7A N1A C9A 80.72(14) . .
C15 C7A N1A C9A -44.16(14) 3_765 .
C2A C3A O3A C22 -8.9(2) . .
C4A C3A O3A C22 170.75(14) . .
C5A C4A O4A C17A 10.6(2) . .
C3A C4A O4A C17A -170.56(13) . .
O15A C15A O16A C16A -2.4(2) . .
N1A C15A O16A C16A 178.28(16) . .
