# Electronic Supplementary Material (ESI) for RSC Sustainability.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RM_CEZ_1_3_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2267667'
loop_
_audit_author_name
_audit_author_address
'Kenneth McClain'
;US Navy, Naval Air Warfare Center, Weapons Division, Research Department, Chemistry Division
United States of America
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C18 H20 O6'
_chemical_formula_sum            'C18 H20 O6'
_chemical_formula_weight         332.36
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.3732(5)
_cell_length_b                   9.3953(8)
_cell_length_c                   13.6384(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.205(3)
_cell_angle_gamma                90
_cell_volume                     801.08(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4442
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.65
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9054.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.3778
_exptl_crystal_description       prism
_exptl_crystal_F_000             352.2259
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.152
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9131
_diffrn_reflns_theta_full        25.3410
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -5
_reflns_number_gt                1325
_reflns_number_total             1468
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.2079
_refine_diff_density_min         -0.2025
_refine_diff_density_rms         0.0452
_refine_ls_d_res_high            0.8303
_refine_ls_d_res_low             7.6887
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0734
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.0734
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.3606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0870
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009)
2.b Idealised Me refined as rotating group:
 C00B(H00a,H00b,H00c), C00C(H00d,H00e,H00f)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
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_refinement_flags_posn
O001 O 0.22693(15) 0.69075(11) 0.11356(7) 0.0220(3) Uani 1.000000 .
O002 O 0.86458(15) 0.85486(11) 0.30540(7) 0.0243(3) Uani 1.000000 .
O003 O 0.57393(16) 0.85316(11) 0.13603(7) 0.0247(3) Uani 1.000000 .
H003 H 0.6846(16) 0.9028(14) 0.1534(4) 0.0370(4) Uiso 1.000000 GR
C004 C 0.4776(2) 0.59913(14) 0.37425(10) 0.0169(3) Uani 1.000000 .
C005 C 0.5444(2) 0.76932(14) 0.21461(10) 0.0185(3) Uani 1.000000 .
C006 C 0.6622(2) 0.68228(14) 0.38352(10) 0.0175(3) Uani 1.000000 .
H006 H 0.7657(2) 0.68105(14) 0.44390(10) 0.0211(4) Uiso 1.000000 R
C007 C 0.3617(2) 0.68549(14) 0.20498(10) 0.0176(3) Uani 1.000000 .
C008 C 0.4343(2) 0.51004(14) 0.45616(10) 0.0178(3) Uani 1.000000 .
H008 H 0.3005(2) 0.46222(14) 0.44590(10) 0.0214(4) Uiso 1.000000 R
C009 C 0.3282(2) 0.60158(14) 0.28429(10) 0.0180(3) Uani 1.000000 .
H009 H 0.2025(2) 0.54517(14) 0.27742(10) 0.0216(4) Uiso 1.000000 R
C00A C 0.6934(2) 0.76628(14) 0.30448(10) 0.0180(3) Uani 1.000000 .
C00B C 0.0161(2) 0.63580(17) 0.10762(11) 0.0252(4) Uani 1.000000 .
H00a H -0.0719(5) 0.6605(10) 0.0427(3) 0.0378(5) Uiso 1.000000 GR
H00b H 0.0227(3) 0.5321(2) 0.1150(8) 0.0378(5) Uiso 1.000000 GR
H00c H -0.0471(6) 0.6771(8) 0.1611(5) 0.0378(5) Uiso 1.000000 GR
C00C C 1.0225(2) 0.85631(17) 0.39594(11) 0.0261(4) Uani 1.000000 .
H00d H 1.1358(9) 0.9241(8) 0.3893(3) 0.0392(5) Uiso 1.000000 GR
H00e H 0.9556(4) 0.8848(11) 0.45180(17) 0.0392(5) Uiso 1.000000 GR
H00f H 1.0841(12) 0.7609(3) 0.4086(4) 0.0392(5) Uiso 1.000000 GR


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
O001 C007 1.3705(15) . ?
O001 C00B 1.4266(17) . ?
O002 C00A 1.3705(17) . ?
O002 C00C 1.4336(16) . ?
O003 H003 0.8400 . ?
O003 C005 1.3722(16) . ?
C004 C006 1.3972(19) . ?
C004 C008 1.4645(18) . ?
C004 C009 1.3993(18) . ?
C005 C007 1.391(2) . ?
C005 C00A 1.3972(19) . ?
C006 H006 0.9500 . ?
C006 C00A 1.3811(19) . ?
C007 C009 1.3880(19) . ?
C008 C008 1.333(3) 3_666 ?
C008 H008 0.9500 . ?
C009 H009 0.9500 . ?
C00B H00a 0.9800 . ?
C00B H00b 0.9800 . ?
C00B H00c 0.9800 . ?
C00C H00d 0.9800 . ?
C00C H00e 0.9800 . ?
C00C H00f 0.9800 . ?

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
C00B O001 C007 117.08(10) . . ?
C00C O002 C00A 115.99(11) . . ?
C005 O003 H003 109.5 . . ?
C008 C004 C006 122.05(12) . . ?
C009 C004 C006 119.18(12) . . ?
C009 C004 C008 118.77(12) . . ?
C007 C005 O003 119.39(12) . . ?
C00A C005 O003 121.59(12) . . ?
C00A C005 C007 119.01(12) . . ?
H006 C006 C004 120.16(8) . . ?
C00A C006 C004 119.68(12) . . ?
C00A C006 H006 120.16(8) . . ?
C005 C007 O001 115.51(12) . . ?
C009 C007 O001 124.44(12) . . ?
C009 C007 C005 120.04(12) . . ?
C008 C008 C004 125.90(16) 3_666 . ?
H008 C008 C004 117.05(7) . . ?
C007 C009 C004 120.75(12) . . ?
H009 C009 C004 119.62(8) . . ?
H009 C009 C007 119.62(8) . . ?
C005 C00A O002 113.56(12) . . ?
C006 C00A O002 125.10(12) . . ?
C006 C00A C005 121.34(12) . . ?
H00a C00B O001 109.5 . . ?
H00b C00B O001 109.5 . . ?
H00b C00B H00a 109.5 . . ?
H00c C00B O001 109.5 . . ?
H00c C00B H00a 109.5 . . ?
H00c C00B H00b 109.5 . . ?
H00d C00C O002 109.5 . . ?
H00e C00C O002 109.5 . . ?
H00e C00C H00d 109.5 . . ?
H00f C00C O002 109.5 . . ?
H00f C00C H00d 109.5 . . ?
H00f C00C H00e 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
(E)-4,4?-(ethene-1,2-diyl)bis(2,6-dimethoxyphenol)
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
