# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2266205'
loop_
_audit_author_name
_audit_author_address
methoxybenzene
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2023-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.12(C28 H24 F2 O4 S)'
_chemical_formula_sum            'C H F O S'
_chemical_formula_weight         80.08
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0930(6)
_cell_length_b                   8.0955(3)
_cell_length_c                   20.7666(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.204(2)
_cell_angle_gamma                90
_cell_volume                     2448.56(16)
_cell_formula_units_Z            34
_cell_measurement_reflns_used    6117
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0502 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.9214.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23539
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         1.398
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4272
_reflns_number_total             6091
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.3339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C21(H21), C12(H12), C17(H17), C28(H28), C5(H5), C8(H8),
 C19(H19), C24(H24), C18(H18), C3(H3), C27(H27), C26(H26), C25(H25), C6(H6),
 C2(H2), C1(H1)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
S1 S 0.95282(3) 0.52716(6) 0.64929(2) 0.03816(13) Uani 1 1 d . . . . .
F1 F 0.77390(8) 0.36905(15) 0.79228(6) 0.0625(3) Uani 1 1 d . . . . .
F2 F 0.84646(8) 0.56536(18) 0.85682(5) 0.0699(4) Uani 1 1 d . . . . .
O2 O 0.97083(9) 0.70173(16) 0.65279(6) 0.0514(3) Uani 1 1 d . . . . .
O1 O 1.02496(8) 0.41780(17) 0.68343(6) 0.0504(3) Uani 1 1 d . . . . .
O3 O 0.72018(12) -0.14305(18) 0.59075(8) 0.0794(5) Uani 1 1 d . . . . .
O4 O 0.49498(10) 0.6219(2) 0.66470(9) 0.0795(5) Uani 1 1 d . . . . .
C10 C 0.81385(11) 0.3235(2) 0.66009(8) 0.0370(4) Uani 1 1 d . . . . .
C13 C 0.85288(10) 0.4920(2) 0.68139(7) 0.0361(4) Uani 1 1 d . . . . .
H13 H 0.8062 0.5746 0.6616 0.043 Uiso 1 1 calc R . . . .
C16 C 0.72991(12) 0.6437(2) 0.76288(8) 0.0432(4) Uani 1 1 d . . . . .
C23 C 0.91526(11) 0.4665(2) 0.56489(8) 0.0422(4) Uani 1 1 d . . . . .
C11 C 0.86001(11) 0.1801(2) 0.68623(8) 0.0442(4) Uani 1 1 d . . . . .
H11 H 0.9128 0.1879 0.7213 0.053 Uiso 1 1 calc R . . . .
C9 C 0.73318(12) 0.3084(2) 0.60957(9) 0.0472(4) Uani 1 1 d . . . . .
H9 H 0.7009 0.4029 0.5918 0.057 Uiso 1 1 calc R . . . .
C21 C 0.64582(12) 0.5856(3) 0.72625(9) 0.0474(4) Uani 1 1 d . . . . .
H21 H 0.6371 0.4728 0.7186 0.057 Uiso 1 1 calc R . . . .
C4 C 0.66687(13) -0.1698(2) 0.52633(9) 0.0484(4) Uani 1 1 d . . . . .
C14 C 0.88519(11) 0.5243(2) 0.75701(8) 0.0416(4) Uani 1 1 d . . . . .
H14A H 0.9287 0.4392 0.7775 0.050 Uiso 1 1 calc R . . . .
H14B H 0.9169 0.6296 0.7645 0.050 Uiso 1 1 calc R . . . .
C15 C 0.80760(12) 0.5267(2) 0.79061(8) 0.0468(4) Uani 1 1 d . . . . .
C20 C 0.57433(13) 0.6943(3) 0.70087(9) 0.0535(5) Uani 1 1 d . . . . .
C12 C 0.82948(13) 0.0272(2) 0.66154(9) 0.0508(5) Uani 1 1 d . . . . .
H12 H 0.8623 -0.0673 0.6787 0.061 Uiso 1 1 calc R . . . .
C17 C 0.74276(14) 0.8121(3) 0.77354(10) 0.0540(5) Uani 1 1 d . . . . .
H17 H 0.7995 0.8526 0.7976 0.065 Uiso 1 1 calc R . . . .
C28 C 0.86237(14) 0.5736(3) 0.51934(9) 0.0594(5) Uani 1 1 d . . . . .
H28 H 0.8486 0.6781 0.5327 0.071 Uiso 1 1 calc R . . . .
C7 C 0.74913(14) 0.0154(2) 0.61073(10) 0.0534(5) Uani 1 1 d . . . . .
C5 C 0.59363(14) -0.2723(3) 0.51974(11) 0.0614(5) Uani 1 1 d . . . . .
H5 H 0.5780 -0.3137 0.5571 0.074 Uiso 1 1 calc R . . . .
C8 C 0.70012(14) 0.1548(3) 0.58534(10) 0.0584(5) Uani 1 1 d . . . . .
H8 H 0.6453 0.1459 0.5522 0.070 Uiso 1 1 calc R . . . .
C19 C 0.58651(15) 0.8613(3) 0.71239(11) 0.0624(6) Uani 1 1 d . . . . .
H19 H 0.5383 0.9345 0.6961 0.075 Uiso 1 1 calc R . . . .
C24 C 0.93720(14) 0.3119(3) 0.54622(10) 0.0611(5) Uani 1 1 d . . . . .
H24 H 0.9731 0.2400 0.5773 0.073 Uiso 1 1 calc R . . . .
C18 C 0.67118(16) 0.9187(3) 0.74838(11) 0.0640(6) Uani 1 1 d . . . . .
H18 H 0.6799 1.0315 0.7557 0.077 Uiso 1 1 calc R . . . .
C3 C 0.68911(15) -0.1067(3) 0.47131(12) 0.0656(6) Uani 1 1 d . . . . .
H3 H 0.7389 -0.0358 0.4761 0.079 Uiso 1 1 calc R . . . .
C27 C 0.82991(17) 0.5252(4) 0.45387(10) 0.0797(8) Uani 1 1 d . . . . .
H27 H 0.7934 0.5964 0.4228 0.096 Uiso 1 1 calc R . . . .
C26 C 0.85146(17) 0.3725(4) 0.43467(11) 0.0832(8) Uani 1 1 d . . . . .
H26 H 0.8298 0.3406 0.3903 0.100 Uiso 1 1 calc R . . . .
C25 C 0.90416(18) 0.2660(4) 0.47947(13) 0.0796(8) Uani 1 1 d . . . . .
H25 H 0.9182 0.1624 0.4655 0.095 Uiso 1 1 calc R . . . .
C6 C 0.54268(18) -0.3134(4) 0.45565(16) 0.0899(9) Uani 1 1 d . . . . .
H6 H 0.4927 -0.3841 0.4501 0.108 Uiso 1 1 calc R . . . .
C2 C 0.6370(2) -0.1497(3) 0.40921(12) 0.0803(8) Uani 1 1 d . . . . .
H2 H 0.6518 -0.1074 0.3717 0.096 Uiso 1 1 calc R . . . .
C1 C 0.5649(2) -0.2520(4) 0.40146(13) 0.0925(9) Uani 1 1 d . . . . .
H1 H 0.5304 -0.2805 0.3589 0.111 Uiso 1 1 calc R . . . .
C22 C 0.41901(17) 0.7243(4) 0.63544(17) 0.1019(10) Uani 1 1 d . . . . .
H22A H 0.4364 0.8028 0.6063 0.153 Uiso 1 1 calc GR . . . .
H22B H 0.3998 0.7819 0.6699 0.153 Uiso 1 1 calc GR . . . .
H22C H 0.3693 0.6576 0.6103 0.153 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.4374(14) . ?
S1 O1 1.4378(13) . ?
S1 C13 1.8244(16) . ?
S1 C23 1.7644(17) . ?
F1 C15 1.378(2) . ?
F2 C15 1.382(2) . ?
O3 C4 1.386(2) . ?
O3 C7 1.383(2) . ?
O4 C20 1.368(2) . ?
O4 C22 1.416(3) . ?
C10 C13 1.506(2) . ?
C10 C11 1.389(2) . ?
C10 C9 1.388(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.540(2) . ?
C16 C21 1.380(2) . ?
C16 C15 1.500(3) . ?
C16 C17 1.386(3) . ?
C23 C28 1.374(3) . ?
C23 C24 1.376(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(3) . ?
C4 C5 1.360(3) . ?
C4 C3 1.371(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(2) . ?
C20 C19 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C7 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.376(3) . ?
C7 C8 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C8 H8 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.381(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.395(3) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.368(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.365(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.361(4) . ?
C25 H25 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.351(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.343(4) . ?
C1 H1 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O2 S1 O1 118.15(8) . . ?
O2 S1 C13 107.37(8) . . ?
O2 S1 C23 109.33(8) . . ?
O1 S1 C13 108.39(8) . . ?
O1 S1 C23 108.85(8) . . ?
C23 S1 C13 103.80(7) . . ?
C7 O3 C4 119.50(15) . . ?
C20 O4 C22 118.6(2) . . ?
C11 C10 C13 121.65(14) . . ?
C9 C10 C13 119.97(15) . . ?
C9 C10 C11 118.22(16) . . ?
S1 C13 H13 108.2 . . ?
C10 C13 S1 109.35(11) . . ?
C10 C13 H13 108.2 . . ?
C10 C13 C14 116.65(14) . . ?
C14 C13 S1 105.97(10) . . ?
C14 C13 H13 108.2 . . ?
C21 C16 C15 120.62(17) . . ?
C21 C16 C17 119.56(18) . . ?
C17 C16 C15 119.81(17) . . ?
C28 C23 S1 119.06(15) . . ?
C28 C23 C24 121.29(18) . . ?
C24 C23 S1 119.63(15) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.51(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 120.96(17) . . ?
C8 C9 H9 119.5 . . ?
C16 C21 H21 119.8 . . ?
C16 C21 C20 120.31(19) . . ?
C20 C21 H21 119.8 . . ?
C5 C4 O3 116.32(18) . . ?
C5 C4 C3 120.90(19) . . ?
C3 C4 O3 122.64(18) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.34(13) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
F1 C15 F2 104.36(14) . . ?
F1 C15 C16 109.77(15) . . ?
F1 C15 C14 109.61(15) . . ?
F2 C15 C16 108.90(15) . . ?
F2 C15 C14 106.49(14) . . ?
C16 C15 C14 116.93(14) . . ?
O4 C20 C21 114.78(19) . . ?
O4 C20 C19 125.0(2) . . ?
C19 C20 C21 120.19(19) . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C7 119.20(18) . . ?
C7 C12 H12 120.4 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.57(19) . . ?
C18 C17 H17 120.2 . . ?
C23 C28 H28 120.2 . . ?
C23 C28 C27 119.5(2) . . ?
C27 C28 H28 120.2 . . ?
O3 C7 C12 115.91(18) . . ?
C8 C7 O3 123.35(17) . . ?
C8 C7 C12 120.64(18) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.41(17) . . ?
C7 C8 H8 120.3 . . ?
C20 C19 H19 120.4 . . ?
C20 C19 C18 119.1(2) . . ?
C18 C19 H19 120.4 . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.2(2) . . ?
C25 C24 H24 120.9 . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.8(2) . . ?
C26 C27 H27 120.1 . . ?
C27 C26 H26 119.5 . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C5 C6 H6 119.6 . . ?
C1 C6 C5 120.9(2) . . ?
C1 C6 H6 119.6 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2 119.4 . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
