# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mw080414b
_database_code_depnum_ccdc_archive 'CCDC 2246512'
loop_
_audit_author_name
_audit_author_address
'Artur Korzanski'
;Adam Mickiewicz University, Faculty of Chemistry, Poznan, Poland
Poland
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_audit_creation_date             2022-09-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            2,3,3',4'-tetramethoxy-trans-stilbene
_chemical_name_systematic        
(E)-1-(3,4-dimethoxystyryl)-2,3-dimethoxybenzene
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H20 O4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.2140(2)
_cell_length_b                   23.4393(8)
_cell_length_c                   25.0160(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3057.27(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      28.4570
_cell_measurement_theta_min      3.5580
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7598
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.511
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  30.00   1.00   15.00    --   16.56 -57.00-120.00   77
  2  ω    -86.00 -49.00   1.00   15.00    --  -17.42 179.00   0.00   37
  3  ω    -91.00 -58.00   1.00   15.00    --  -17.42-179.00  30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0423339000
_diffrn_orient_matrix_UB_12      0.0138313000
_diffrn_orient_matrix_UB_13      0.0236340000
_diffrn_orient_matrix_UB_21      0.1081629000
_diffrn_orient_matrix_UB_22      0.0183478000
_diffrn_orient_matrix_UB_23      -0.0009903000
_diffrn_orient_matrix_UB_31      -0.0707277000
_diffrn_orient_matrix_UB_32      0.0196817000
_diffrn_orient_matrix_UB_33      -0.0156625000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2699
_reflns_number_total             3350
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+1.5264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C18(H18), C14(H14), C17(H17), C4(H4), C5(H5), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O19 O -0.0211(2) 0.44505(4) 0.34281(4) 0.0232(3) Uani 1 1 d . . . . .
O9 O 1.0197(2) 0.18225(4) 0.45293(4) 0.0195(3) Uani 1 1 d . . . . .
O7 O 1.3430(2) 0.09352(4) 0.44334(4) 0.0232(3) Uani 1 1 d . . . . .
O21 O 0.3442(2) 0.43018(4) 0.41066(4) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.8928(3) 0.17373(6) 0.36154(6) 0.0170(3) Uani 1 1 d . . . . .
C2 C 1.0450(3) 0.15551(6) 0.40399(5) 0.0167(3) Uani 1 1 d . . . . .
C3 C 1.2072(3) 0.10796(6) 0.39862(6) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.3813(3) 0.29116(6) 0.34024(6) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.7342(3) 0.22501(6) 0.36748(5) 0.0178(3) Uani 1 1 d . . . . .
H11 H 0.7797 0.2505 0.3943 0.021 Uiso 1 1 calc R U . . .
C6 C 0.9059(3) 0.14363(6) 0.31313(6) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.8065 0.1552 0.2842 0.023 Uiso 1 1 calc R U . . .
C18 C 0.1799(3) 0.29962(6) 0.30495(6) 0.0186(3) Uani 1 1 d . . . . .
H18 H 0.1372 0.2708 0.2810 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4381(3) 0.33513(6) 0.37696(6) 0.0181(3) Uani 1 1 d . . . . .
H14 H 0.5713 0.3302 0.4013 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0399(3) 0.35031(6) 0.30455(6) 0.0187(3) Uani 1 1 d . . . . .
H17 H -0.0936 0.3552 0.2803 0.022 Uiso 1 1 calc R U . . .
C4 C 1.2171(3) 0.07867(6) 0.35049(6) 0.0201(3) Uani 1 1 d . . . . .
H4 H 1.3238 0.0471 0.3466 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0994(3) 0.39326(6) 0.34016(6) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.2997(3) 0.38510(6) 0.37737(5) 0.0180(3) Uani 1 1 d . . . . .
C5 C 1.0656(3) 0.09697(6) 0.30811(6) 0.0198(3) Uani 1 1 d . . . . .
H5 H 1.0719 0.0774 0.2758 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5298(3) 0.23825(6) 0.33770(6) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.4767 0.2112 0.3129 0.022 Uiso 1 1 calc R U . . .
C22 C 0.5421(3) 0.42340(7) 0.44962(6) 0.0235(4) Uani 1 1 d . . . . .
H22A H 0.7029 0.4170 0.4319 0.035 Uiso 1 1 calc R U . . .
H22B H 0.5030 0.3914 0.4721 0.035 Uiso 1 1 calc R U . . .
H22C H 0.5534 0.4573 0.4710 0.035 Uiso 1 1 calc R U . . .
C20 C -0.2203(3) 0.45544(7) 0.30496(6) 0.0239(4) Uani 1 1 d . . . . .
H20A H -0.1506 0.4543 0.2695 0.036 Uiso 1 1 calc R U . . .
H20B H -0.2940 0.4923 0.3114 0.036 Uiso 1 1 calc R U . . .
H20C H -0.3505 0.4267 0.3085 0.036 Uiso 1 1 calc R U . . .
C10 C 1.2423(3) 0.21318(7) 0.47050(6) 0.0244(4) Uani 1 1 d . . . . .
H10A H 1.2644 0.2465 0.4487 0.037 Uiso 1 1 calc R U . . .
H10B H 1.3910 0.1893 0.4675 0.037 Uiso 1 1 calc R U . . .
H10C H 1.2202 0.2244 0.5071 0.037 Uiso 1 1 calc R U . . .
C8 C 1.5340(3) 0.05024(6) 0.43755(7) 0.0238(4) Uani 1 1 d . . . . .
H8A H 1.6537 0.0613 0.4103 0.036 Uiso 1 1 calc R U . . .
H8B H 1.4535 0.0150 0.4276 0.036 Uiso 1 1 calc R U . . .
H8C H 1.6231 0.0454 0.4708 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O19 C16 1.3687(17) . ?
O19 C20 1.4264(19) . ?
O9 C2 1.3818(16) . ?
O9 C10 1.4373(19) . ?
O7 C3 1.3665(18) . ?
O7 C8 1.4289(18) . ?
O21 C15 1.3654(17) . ?
O21 C22 1.4278(19) . ?
C1 C2 1.393(2) . ?
C1 C11 1.467(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.406(2) . ?
C3 C4 1.387(2) . ?
C13 C18 1.386(2) . ?
C13 C14 1.412(2) . ?
C13 C12 1.463(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.337(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.395(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.380(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C16 C15 1.412(2) . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
_geom_angle_publ_flag
C16 O19 C20 116.97(12) . . ?
C2 O9 C10 115.00(12) . . ?
C3 O7 C8 116.99(12) . . ?
C15 O21 C22 116.94(12) . . ?
C2 C1 C11 119.69(13) . . ?
C2 C1 C6 118.43(13) . . ?
C6 C1 C11 121.80(13) . . ?
O9 C2 C1 118.82(13) . . ?
O9 C2 C3 120.12(13) . . ?
C1 C2 C3 120.87(13) . . ?
O7 C3 C2 115.46(13) . . ?
O7 C3 C4 124.67(14) . . ?
C4 C3 C2 119.86(14) . . ?
C18 C13 C14 117.95(13) . . ?
C18 C13 C12 119.63(13) . . ?
C14 C13 C12 122.41(14) . . ?
C1 C11 H11 117.2 . . ?
C12 C11 C1 125.70(13) . . ?
C12 C11 H11 117.2 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.43(14) . . ?
C5 C6 H6 119.8 . . ?
C13 C18 H18 119.2 . . ?
C13 C18 C17 121.55(14) . . ?
C17 C18 H18 119.2 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.08(14) . . ?
C15 C14 H14 119.5 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.94(14) . . ?
C16 C17 H17 120.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.22(14) . . ?
C5 C4 H4 120.4 . . ?
O19 C16 C17 125.10(14) . . ?
O19 C16 C15 115.33(13) . . ?
C17 C16 C15 119.57(14) . . ?
O21 C15 C14 125.03(14) . . ?
O21 C15 C16 115.04(13) . . ?
C14 C15 C16 119.90(13) . . ?
C6 C5 C4 121.19(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C13 C12 H12 116.8 . . ?
C11 C12 C13 126.46(14) . . ?
C11 C12 H12 116.8 . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O9 C10 H10A 109.5 . . ?
O9 C10 H10B 109.5 . . ?
O9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O19 C16 C15 O21 -0.04(19) . . . . ?
O19 C16 C15 C14 -178.08(13) . . . . ?
O9 C2 C3 O7 -3.7(2) . . . . ?
O9 C2 C3 C4 175.11(14) . . . . ?
O7 C3 C4 C5 178.73(14) . . . . ?
C1 C2 C3 O7 -178.69(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C11 C12 C13 -174.91(14) . . . . ?
C1 C6 C5 C4 -0.1(2) . . . . ?
C2 C1 C11 C12 -159.62(15) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C13 C18 C17 C16 -0.6(2) . . . . ?
C13 C14 C15 O21 -178.68(14) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C11 C1 C2 O9 7.7(2) . . . . ?
C11 C1 C2 C3 -177.22(14) . . . . ?
C11 C1 C6 C5 177.16(14) . . . . ?
C6 C1 C2 O9 -175.35(13) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C6 C1 C11 C12 23.6(2) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C18 C13 C12 C11 177.23(14) . . . . ?
C18 C17 C16 O19 178.75(14) . . . . ?
C18 C17 C16 C15 -1.0(2) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
C14 C13 C12 C11 -1.5(2) . . . . ?
C17 C16 C15 O21 179.74(13) . . . . ?
C17 C16 C15 C14 1.7(2) . . . . ?
C12 C13 C18 C17 -177.42(13) . . . . ?
C12 C13 C14 C15 178.10(14) . . . . ?
C22 O21 C15 C14 -3.2(2) . . . . ?
C22 O21 C15 C16 178.88(13) . . . . ?
C20 O19 C16 C17 -1.3(2) . . . . ?
C20 O19 C16 C15 178.48(13) . . . . ?
C10 O9 C2 C1 -114.96(15) . . . . ?
C10 O9 C2 C3 69.94(17) . . . . ?
C8 O7 C3 C2 -172.10(13) . . . . ?
C8 O7 C3 C4 9.2(2) . . . . ?

_olex2_date_sample_data_collection 2021-07-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.469
_oxdiff_exptl_absorpt_empirical_full_min 0.816
