# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_rm005
_database_code_depnum_ccdc_archive 'CCDC 2075144'
loop_
_audit_author_name
_audit_author_address
'Takeshi Fujita'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2021-04-03 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-4-[3-methyl-5-(prop-1-en-1-yl)benzofuran-2-yl]phenol
_chemical_name_common            Eupomatenoid-6
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.768(2)
_cell_length_b                   18.775(9)
_cell_length_c                   31.234(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2796(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1512
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11851
_diffrn_reflns_av_R_equivalents  0.1232
_diffrn_reflns_av_sigmaI/netI    0.1015
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2462
_reflns_number_gt                1363
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+5.9798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2950(6) 0.03432(15) 0.64046(9) 0.0354(9) Uani 1 1 d . . .
C1 C 0.4828(10) 0.0302(2) 0.60606(13) 0.0316(11) Uani 1 1 d . . .
C2 C 0.6318(10) 0.0922(2) 0.60166(13) 0.0303(11) Uani 1 1 d . . .
C3 C 0.5917(10) 0.2100(2) 0.64715(13) 0.0320(11) Uani 1 1 d . . .
H3 H 0.7303 0.2366 0.6323 0.038 Uiso 1 1 calc R . .
C4 C 0.4466(10) 0.2403(2) 0.68145(14) 0.0337(12) Uani 1 1 d . . .
C5 C 0.2431(10) 0.1995(3) 0.70345(15) 0.0361(12) Uani 1 1 d . . .
H5 H 0.1456 0.2205 0.7268 0.043 Uiso 1 1 calc R . .
C6 C 0.1808(10) 0.1294(2) 0.69199(14) 0.0367(12) Uani 1 1 d . . .
H6 H 0.0446 0.1022 0.7070 0.044 Uiso 1 1 calc R . .
C7 C 0.5305(10) 0.1395(2) 0.63478(13) 0.0315(11) Uani 1 1 d . . .
C8 C 0.3263(10) 0.1019(2) 0.65791(14) 0.0332(12) Uani 1 1 d . . .
C9 C 0.8550(10) 0.1114(2) 0.56989(14) 0.0379(12) Uani 1 1 d . . .
H9 H 1.0019 0.0749 0.5702 0.057 Uiso 1 1 calc R . .
H9A H 0.9366 0.1576 0.5775 0.057 Uiso 1 1 calc R . .
H9B H 0.7725 0.1142 0.5412 0.057 Uiso 1 1 calc R . .
C10 C 0.5009(11) 0.3162(3) 0.69605(15) 0.0346(13) Uani 1 1 d . . .
H10 H 0.407(10) 0.327(2) 0.7183(14) 0.039(15) Uiso 1 1 d . . .
C11 C 0.6915(12) 0.3581(3) 0.68239(17) 0.0425(14) Uani 1 1 d . . .
H11 H 0.804(12) 0.345(3) 0.6585(17) 0.066(18) Uiso 1 1 d . . .
C12 C 0.7330(12) 0.4346(2) 0.69689(16) 0.0478(14) Uani 1 1 d . . .
H12 H 0.6807 0.4671 0.6736 0.072 Uiso 1 1 calc R . .
H12A H 0.9303 0.4421 0.7045 0.072 Uiso 1 1 calc R . .
H12B H 0.6149 0.4440 0.7219 0.072 Uiso 1 1 calc R . .
C13 C 0.4792(9) -0.0381(2) 0.58317(14) 0.0318(11) Uani 1 1 d . . .
C14 C 0.3055(11) -0.0927(3) 0.59674(17) 0.0490(15) Uani 1 1 d . . .
H14 H 0.1873 -0.0854 0.6208 0.059 Uiso 1 1 calc R . .
C15 C 0.3004(12) -0.1585(3) 0.57570(15) 0.0510(15) Uani 1 1 d . . .
H15 H 0.1836 -0.1958 0.5859 0.061 Uiso 1 1 calc R . .
C16 C 0.4635(10) -0.1687(2) 0.54055(14) 0.0321(11) Uani 1 1 d . . .
C17 C 0.6367(11) -0.1158(2) 0.52588(17) 0.0506(15) Uani 1 1 d . . .
H17 H 0.7520 -0.1234 0.5015 0.061 Uiso 1 1 calc R . .
C18 C 0.6411(12) -0.0505(3) 0.54726(17) 0.0502(15) Uani 1 1 d . . .
H18 H 0.7587 -0.0135 0.5368 0.060 Uiso 1 1 calc R . .
O2 O 0.4456(7) -0.23453(15) 0.51943(10) 0.0402(9) Uani 1 1 d . . .
H2 H 0.5891 -0.2405 0.5042 0.060 Uiso 1 1 calc R . .


_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
O1 C8 1.388(5) . ?
O1 C1 1.401(5) . ?
C1 C2 1.371(6) . ?
C1 C13 1.469(6) . ?
C2 C7 1.447(6) . ?
C2 C9 1.499(6) . ?
C3 C4 1.396(6) . ?
C3 C7 1.409(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(6) . ?
C4 C10 1.518(7) . ?
C5 C6 1.395(6) . ?
C5 H5 0.9500 . ?
C6 C8 1.372(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(6) . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.276(7) . ?
C10 H10 0.85(5) . ?
C11 C12 1.519(7) . ?
C11 H11 0.95(5) . ?
C12 H12 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C18 1.381(6) . ?
C13 C14 1.384(6) . ?
C14 C15 1.399(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.359(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(6) . ?
C16 O2 1.404(5) . ?
C17 C18 1.397(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O2 H2 0.8400 . ?

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
C8 O1 C1 106.4(3) . . ?
C2 C1 O1 111.2(4) . . ?
C2 C1 C13 134.4(4) . . ?
O1 C1 C13 114.4(4) . . ?
C1 C2 C7 106.1(4) . . ?
C1 C2 C9 129.6(4) . . ?
C7 C2 C9 124.3(4) . . ?
C4 C3 C7 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C7 C3 H3 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 C10 121.9(4) . . ?
C5 C4 C10 118.6(4) . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C8 C6 C5 116.6(4) . . ?
C8 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C8 C7 C3 118.4(4) . . ?
C8 C7 C2 106.9(4) . . ?
C3 C7 C2 134.7(4) . . ?
C6 C8 O1 126.5(4) . . ?
C6 C8 C7 124.0(4) . . ?
O1 C8 C7 109.4(4) . . ?
C2 C9 H9 109.5 . . ?
C2 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C11 C10 C4 126.9(5) . . ?
C11 C10 H10 120(3) . . ?
C4 C10 H10 112(3) . . ?
C10 C11 C12 125.2(5) . . ?
C10 C11 H11 120(3) . . ?
C12 C11 H11 114(3) . . ?
C11 C12 H12 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C18 C13 C14 117.3(4) . . ?
C18 C13 C1 122.4(4) . . ?
C14 C13 C1 120.3(4) . . ?
C13 C14 C15 121.3(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 O2 118.0(4) . . ?
C17 C16 O2 121.2(4) . . ?
C16 C17 C18 119.0(5) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 121.8(5) . . ?
C13 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C16 O2 H2 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
C8 O1 C1 C2 0.6(5) . . . . ?
C8 O1 C1 C13 -179.7(4) . . . . ?
O1 C1 C2 C7 -1.0(5) . . . . ?
C13 C1 C2 C7 179.5(5) . . . . ?
O1 C1 C2 C9 179.3(4) . . . . ?
C13 C1 C2 C9 -0.2(9) . . . . ?
C7 C3 C4 C5 0.7(6) . . . . ?
C7 C3 C4 C10 -179.4(4) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C10 C4 C5 C6 179.9(4) . . . . ?
C4 C5 C6 C8 -0.4(7) . . . . ?
C4 C3 C7 C8 -0.7(6) . . . . ?
C4 C3 C7 C2 179.2(5) . . . . ?
C1 C2 C7 C8 1.0(5) . . . . ?
C9 C2 C7 C8 -179.3(4) . . . . ?
C1 C2 C7 C3 -178.9(5) . . . . ?
C9 C2 C7 C3 0.8(8) . . . . ?
C5 C6 C8 O1 -178.6(4) . . . . ?
C5 C6 C8 C7 0.4(7) . . . . ?
C1 O1 C8 C6 179.1(4) . . . . ?
C1 O1 C8 C7 0.0(5) . . . . ?
C3 C7 C8 C6 0.2(7) . . . . ?
C2 C7 C8 C6 -179.8(4) . . . . ?
C3 C7 C8 O1 179.3(4) . . . . ?
C2 C7 C8 O1 -0.6(5) . . . . ?
C3 C4 C10 C11 -6.3(8) . . . . ?
C5 C4 C10 C11 173.6(5) . . . . ?
C4 C10 C11 C12 178.0(5) . . . . ?
C2 C1 C13 C18 -3.5(8) . . . . ?
O1 C1 C13 C18 177.0(4) . . . . ?
C2 C1 C13 C14 177.8(5) . . . . ?
O1 C1 C13 C14 -1.7(6) . . . . ?
C18 C13 C14 C15 1.9(8) . . . . ?
C1 C13 C14 C15 -179.4(5) . . . . ?
C13 C14 C15 C16 -1.7(8) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C14 C15 C16 O2 -177.9(5) . . . . ?
C15 C16 C17 C18 -0.8(8) . . . . ?
O2 C16 C17 C18 178.2(5) . . . . ?
C14 C13 C18 C17 -1.6(8) . . . . ?
C1 C13 C18 C17 179.7(5) . . . . ?
C16 C17 C18 C13 1.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.057
