# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2019Mar_sampleA
_database_code_depnum_ccdc_archive 'CCDC 1915566'
loop_
_audit_author_name
_audit_author_address
'Kiyoshi Tsuge'
;University of Toyama
Japan
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_weight         300.35
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ab'
_space_group_IT_number           41
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   8.05576(16)
_cell_length_b                   24.7866(5)
_cell_length_c                   15.4543(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3085.84(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14195
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      68.14
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280.00
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  0.895

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            16768
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_theta_max         68.141
_diffrn_reflns_theta_min         3.566
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2780
_reflns_number_gt                2682
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0632
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2780
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0339P)²+0.6254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.69572(15) 0.57746(5) 0.64436(8) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.85992(18) 0.41961(5) 0.49810(10) 0.0443(4) Uani 1 1 d . . . . .
O3 O 0.72129(15) 0.70294(4) 0.56202(10) 0.0373(3) Uani 1 1 d . . . . .
O4 O 0.48611(16) 0.66387(5) 0.60916(10) 0.0430(3) Uani 1 1 d . . . . .
C1 C 0.7330(2) 0.52417(6) 0.63885(13) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.7620(2) 0.49851(6) 0.56328(13) 0.0304(4) Uani 1 1 d . . . . .
C3 C 0.7420(2) 0.52613(7) 0.47713(13) 0.0337(4) Uani 1 1 d . . . . .
H3A H 0.681994 0.502028 0.436743 0.040 Uiso 1 1 calc R U . . .
H3B H 0.852683 0.533860 0.452205 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6453(2) 0.57887(7) 0.48797(12) 0.0304(4) Uani 1 1 d . . . . .
H4 H 0.527194 0.569535 0.501192 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7173(2) 0.60864(6) 0.56661(12) 0.0294(4) Uani 1 1 d . . . . .
H5 H 0.837952 0.615990 0.557069 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7381(2) 0.49865(7) 0.72614(12) 0.0347(4) Uani 1 1 d . . . . .
H6A H 0.646615 0.513165 0.762009 0.042 Uiso 1 1 calc R U . . .
H6B H 0.844310 0.507814 0.754842 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7216(2) 0.43750(8) 0.71985(15) 0.0380(4) Uani 1 1 d . . . . .
H7A H 0.746499 0.421048 0.776767 0.046 Uiso 1 1 calc R U . . .
H7B H 0.606187 0.427956 0.704052 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8404(2) 0.41534(7) 0.65216(14) 0.0377(4) Uani 1 1 d . . . . .
H8A H 0.955809 0.420172 0.672758 0.045 Uiso 1 1 calc R U . . .
H8B H 0.820440 0.376165 0.645264 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8216(2) 0.44260(6) 0.56512(14) 0.0337(4) Uani 1 1 d . . . . .
C10 C 0.6465(2) 0.61565(7) 0.40963(12) 0.0320(4) Uani 1 1 d . . . . .
C11 C 0.7945(3) 0.63193(8) 0.37136(13) 0.0390(4) Uani 1 1 d . . . . .
H11 H 0.896811 0.617592 0.391524 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7940(3) 0.66884(9) 0.30413(15) 0.0479(5) Uani 1 1 d . . . . .
H12 H 0.895759 0.679718 0.278385 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6455(3) 0.68992(9) 0.27438(14) 0.0509(6) Uani 1 1 d . . . . .
H13 H 0.645356 0.715506 0.228608 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4977(3) 0.67374(8) 0.31130(14) 0.0471(5) Uani 1 1 d . . . . .
H14 H 0.395709 0.687959 0.290477 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4974(3) 0.63677(8) 0.37872(13) 0.0386(4) Uani 1 1 d . . . . .
H15 H 0.395257 0.625798 0.403918 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6261(2) 0.66128(7) 0.58264(11) 0.0302(4) Uani 1 1 d . . . . .
C17 C 0.6487(3) 0.75689(7) 0.56562(17) 0.0441(5) Uani 1 1 d . . . . .
H17A H 0.721783 0.781118 0.599429 0.053 Uiso 1 1 calc R U . . .
H17B H 0.539405 0.755323 0.594806 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6285(4) 0.77811(10) 0.47777(17) 0.0617(7) Uani 1 1 d . . . . .
H18A H 0.592342 0.815818 0.480644 0.074 Uiso 1 1 calc R U . . .
H18B H 0.544964 0.756749 0.446912 0.074 Uiso 1 1 calc R U . . .
H18C H 0.734633 0.775950 0.446983 0.074 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.357(2) . ?
O1 C5 1.439(2) . ?
O2 C9 1.222(2) . ?
O3 C16 1.325(2) . ?
O3 C17 1.461(2) . ?
O4 C16 1.201(2) . ?
C1 C2 1.350(3) . ?
C1 C6 1.490(3) . ?
C2 C9 1.467(2) . ?
C2 C3 1.506(3) . ?
C3 C4 1.531(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.516(2) . ?
C4 C5 1.535(2) . ?
C4 H4 1.0000 . ?
C5 C16 1.518(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.390(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.465(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C1 O1 C5 116.33(14) . . ?
C16 O3 C17 118.19(15) . . ?
C2 C1 O1 123.42(17) . . ?
C2 C1 C6 125.33(15) . . ?
O1 C1 C6 111.25(15) . . ?
C1 C2 C9 119.00(17) . . ?
C1 C2 C3 122.15(14) . . ?
C9 C2 C3 118.80(16) . . ?
C2 C3 C4 110.24(15) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C10 C4 C3 115.01(15) . . ?
C10 C4 C5 109.91(14) . . ?
C3 C4 C5 107.74(14) . . ?
C10 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
O1 C5 C16 105.48(14) . . ?
O1 C5 C4 110.92(12) . . ?
C16 C5 C4 111.06(14) . . ?
O1 C5 H5 109.8 . . ?
C16 C5 H5 109.8 . . ?
C4 C5 H5 109.8 . . ?
C1 C6 C7 111.21(16) . . ?
C1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.37(16) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 112.79(15) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O2 C9 C2 120.45(18) . . ?
O2 C9 C8 121.34(15) . . ?
C2 C9 C8 118.16(17) . . ?
C11 C10 C15 118.94(17) . . ?
C11 C10 C4 121.34(17) . . ?
C15 C10 C4 119.57(17) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O4 C16 O3 125.71(16) . . ?
O4 C16 C5 123.78(16) . . ?
O3 C16 C5 110.50(14) . . ?
O3 C17 C18 109.74(18) . . ?
O3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5 O1 C1 C2 -10.9(2) . . . . ?
C5 O1 C1 C6 168.82(14) . . . . ?
O1 C1 C2 C9 172.43(15) . . . . ?
C6 C1 C2 C9 -7.2(3) . . . . ?
O1 C1 C2 C3 -5.0(2) . . . . ?
C6 C1 C2 C3 175.32(18) . . . . ?
C1 C2 C3 C4 -14.5(2) . . . . ?
C9 C2 C3 C4 168.03(15) . . . . ?
C2 C3 C4 C10 168.36(15) . . . . ?
C2 C3 C4 C5 45.42(19) . . . . ?
C1 O1 C5 C16 165.33(13) . . . . ?
C1 O1 C5 C4 44.99(19) . . . . ?
C10 C4 C5 O1 171.76(14) . . . . ?
C3 C4 C5 O1 -62.23(18) . . . . ?
C10 C4 C5 C16 54.80(19) . . . . ?
C3 C4 C5 C16 -179.19(14) . . . . ?
C2 C1 C6 C7 -19.4(3) . . . . ?
O1 C1 C6 C7 160.90(15) . . . . ?
C1 C6 C7 C8 48.6(2) . . . . ?
C6 C7 C8 C9 -53.6(2) . . . . ?
C1 C2 C9 O2 -174.87(17) . . . . ?
C3 C2 C9 O2 2.7(2) . . . . ?
C1 C2 C9 C8 2.7(2) . . . . ?
C3 C2 C9 C8 -179.76(16) . . . . ?
C7 C8 C9 O2 -154.28(17) . . . . ?
C7 C8 C9 C2 28.2(2) . . . . ?
C3 C4 C10 C11 -54.0(2) . . . . ?
C5 C4 C10 C11 67.8(2) . . . . ?
C3 C4 C10 C15 130.57(18) . . . . ?
C5 C4 C10 C15 -107.66(18) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C4 C10 C11 C12 -174.92(18) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C4 C10 C15 C14 175.03(16) . . . . ?
C17 O3 C16 O4 -4.5(3) . . . . ?
C17 O3 C16 C5 174.42(16) . . . . ?
O1 C5 C16 O4 -49.7(2) . . . . ?
C4 C5 C16 O4 70.5(2) . . . . ?
O1 C5 C16 O3 131.28(14) . . . . ?
C4 C5 C16 O3 -108.47(16) . . . . ?
C16 O3 C17 C18 -109.6(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
