# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_180519b
_database_code_depnum_ccdc_archive 'CCDC 1865404'
loop_
_audit_author_name
_audit_author_address
'Yingping Song'
;Yantai Institute of Coastal Zone Research
China
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_absolute_configuration R/S
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.50 H15 O2'
_chemical_formula_weight         137.20

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 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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.0302(7)
_cell_length_b                   7.6119(8)
_cell_length_c                   7.7844(9)
_cell_angle_alpha                94.191(9)
_cell_angle_beta                 109.731(10)
_cell_angle_gamma                97.560(9)
_cell_volume                     385.61(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1527
_cell_measurement_theta_min      5.9530
_cell_measurement_theta_max      71.1330

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             152
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8557
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.1281
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2041
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.91
_diffrn_reflns_theta_max         66.03
_reflns_number_total             1470
_reflns_number_gt                1431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0528P)²+0.0307P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         1470
_refine_ls_number_parameters     179
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.091
_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 0.5728(2) 0.48751(19) 0.58364(19) 0.0313(3) Uani 1 1 d . . .
O2 O 0.7782(2) 0.9502(2) 0.8187(2) 0.0412(4) Uani 1 1 d . . .
H2 H 0.6828 1.0039 0.8123 0.062 Uiso 1 1 calc R . .
O3 O 0.2169(2) 0.0884(3) -0.0045(2) 0.0449(4) Uani 1 1 d . . .
H3 H 0.0944 0.0542 -0.0616 0.067 Uiso 1 1 calc R . .
O4 O 0.4497(4) 0.1403(3) 0.7597(3) 0.0627(6) Uani 1 1 d . . .
H4E H 0.4693 0.2420 0.7243 0.075 Uiso 1 1 d R . .
H4F H 0.3785 0.1462 0.8284 0.075 Uiso 1 1 d R . .
C1 C 0.6239(3) 0.6347(3) 0.7305(3) 0.0327(5) Uani 1 1 d . . .
C2 C 0.7127(3) 0.8062(3) 0.6718(3) 0.0320(5) Uani 1 1 d . . .
H2A H 0.6052 0.8393 0.5674 0.038 Uiso 1 1 calc R . .
C3 C 0.8911(3) 0.7778(3) 0.6127(3) 0.0370(5) Uani 1 1 d . . .
H3A H 0.9976 0.7405 0.7125 0.044 Uiso 1 1 calc R . .
H3B H 0.9480 0.8884 0.5805 0.044 Uiso 1 1 calc R . .
C4 C 0.8146(4) 0.6345(3) 0.4471(3) 0.0382(5) Uani 1 1 d . . .
H4A H 0.9298 0.6112 0.4122 0.046 Uiso 1 1 calc R . .
H4B H 0.7191 0.6792 0.3446 0.046 Uiso 1 1 calc R . .
C5 C 0.7084(3) 0.4584(3) 0.4819(3) 0.0308(4) Uani 1 1 d . . .
C6 C 0.5635(3) 0.3560(3) 0.2936(3) 0.0328(5) Uani 1 1 d . . .
H6 H 0.6400 0.3592 0.2092 0.039 Uiso 1 1 calc R . .
C7 C 0.4809(3) 0.1577(3) 0.2961(3) 0.0311(5) Uani 1 1 d . . .
H7 H 0.4993 0.1415 0.4241 0.037 Uiso 1 1 calc R . .
C8 C 0.2499(3) 0.1283(3) 0.1886(3) 0.0364(5) Uani 1 1 d . . .
C9 C 0.1948(4) 0.3113(4) 0.2233(3) 0.0453(6) Uani 1 1 d . . .
H9A H 0.1863 0.3305 0.3449 0.054 Uiso 1 1 calc R . .
H9B H 0.0651 0.3242 0.1322 0.054 Uiso 1 1 calc R . .
C10 C 0.3710(4) 0.4405(3) 0.2070(4) 0.0434(6) Uani 1 1 d . . .
H10A H 0.3837 0.5571 0.2728 0.052 Uiso 1 1 calc R . .
H10B H 0.3497 0.4533 0.0791 0.052 Uiso 1 1 calc R . .
C11 C 0.4163(4) 0.6537(4) 0.7442(4) 0.0465(6) Uani 1 1 d . . .
H11A H 0.3604 0.5461 0.7794 0.070 Uiso 1 1 calc R . .
H11B H 0.3249 0.6745 0.6271 0.070 Uiso 1 1 calc R . .
H11C H 0.4328 0.7526 0.8349 0.070 Uiso 1 1 calc R . .
C12 C 0.7658(4) 0.5904(4) 0.9115(3) 0.0459(6) Uani 1 1 d . . .
H12A H 0.9009 0.5933 0.9069 0.069 Uiso 1 1 calc R . .
H12B H 0.7156 0.4732 0.9322 0.069 Uiso 1 1 calc R . .
H12C H 0.7707 0.6765 1.0100 0.069 Uiso 1 1 calc R . .
C13 C 0.8675(3) 0.3495(3) 0.5847(3) 0.0399(5) Uani 1 1 d . . .
H13A H 0.8010 0.2484 0.6216 0.060 Uiso 1 1 calc R . .
H13B H 0.9656 0.4225 0.6917 0.060 Uiso 1 1 calc R . .
H13C H 0.9364 0.3087 0.5057 0.060 Uiso 1 1 calc R . .
C14 C 0.5912(4) 0.0245(3) 0.2278(4) 0.0446(6) Uani 1 1 d . . .
H14A H 0.5986 0.0515 0.1115 0.067 Uiso 1 1 calc R . .
H14B H 0.5172 -0.0942 0.2136 0.067 Uiso 1 1 calc R . .
H14C H 0.7272 0.0322 0.3154 0.067 Uiso 1 1 calc R . .
C15 C 0.1353(4) -0.0229(4) 0.2491(4) 0.0561(7) Uani 1 1 d . . .
H15A H 0.1851 -0.1315 0.2299 0.084 Uiso 1 1 calc R . .
H15B H -0.0084 -0.0371 0.1784 0.084 Uiso 1 1 calc R . .
H15C H 0.1563 0.0039 0.3772 0.084 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 C1 1.456(3) . ?
O1 C5 1.458(3) . ?
O2 C2 1.432(3) . ?
O2 H2 0.8200 . ?
O3 C8 1.445(3) . ?
O3 H3 0.8200 . ?
O4 H4E 0.8499 . ?
O4 H4F 0.8500 . ?
C1 C12 1.518(3) . ?
C1 C11 1.523(3) . ?
C1 C2 1.539(3) . ?
C2 C3 1.509(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.522(3) . ?
C5 C6 1.552(3) . ?
C6 C10 1.542(3) . ?
C6 C7 1.548(3) . ?
C6 H6 0.9800 . ?
C7 C14 1.522(3) . ?
C7 C8 1.532(3) . ?
C7 H7 0.9800 . ?
C8 C15 1.512(4) . ?
C8 C9 1.523(4) . ?
C9 C10 1.524(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 O1 C5 122.15(16) . . ?
C2 O2 H2 109.5 . . ?
C8 O3 H3 109.5 . . ?
H4E O4 H4F 108.8 . . ?
O1 C1 C12 111.68(19) . . ?
O1 C1 C11 102.97(18) . . ?
C12 C1 C11 110.0(2) . . ?
O1 C1 C2 109.65(16) . . ?
C12 C1 C2 112.50(18) . . ?
C11 C1 C2 109.59(19) . . ?
O2 C2 C3 109.20(17) . . ?
O2 C2 C1 110.85(17) . . ?
C3 C2 C1 111.25(18) . . ?
O2 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C2 C3 C4 108.40(18) . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 C5 113.54(19) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 C13 110.00(18) . . ?
O1 C5 C4 112.14(18) . . ?
C13 C5 C4 110.14(19) . . ?
O1 C5 C6 104.33(16) . . ?
C13 C5 C6 111.80(18) . . ?
C4 C5 C6 108.31(17) . . ?
C10 C6 C7 104.98(18) . . ?
C10 C6 C5 113.19(18) . . ?
C7 C6 C5 115.58(16) . . ?
C10 C6 H6 107.6 . . ?
C7 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C14 C7 C8 113.38(19) . . ?
C14 C7 C6 114.60(19) . . ?
C8 C7 C6 106.62(18) . . ?
C14 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
O3 C8 C15 109.39(19) . . ?
O3 C8 C9 109.4(2) . . ?
C15 C8 C9 114.8(2) . . ?
O3 C8 C7 108.38(17) . . ?
C15 C8 C7 112.1(2) . . ?
C9 C8 C7 102.56(18) . . ?
C8 C9 C10 103.5(2) . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.0 . . ?
C9 C10 C6 105.04(19) . . ?
C9 C10 H10A 110.7 . . ?
C6 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C6 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C12 -82.3(2) . . . . ?
C5 O1 C1 C11 159.66(19) . . . . ?
C5 O1 C1 C2 43.1(3) . . . . ?
O1 C1 C2 O2 -175.77(17) . . . . ?
C12 C1 C2 O2 -50.8(2) . . . . ?
C11 C1 C2 O2 71.9(2) . . . . ?
O1 C1 C2 C3 -54.1(2) . . . . ?
C12 C1 C2 C3 70.9(2) . . . . ?
C11 C1 C2 C3 -166.4(2) . . . . ?
O2 C2 C3 C4 -175.62(19) . . . . ?
C1 C2 C3 C4 61.7(2) . . . . ?
C2 C3 C4 C5 -55.7(3) . . . . ?
C1 O1 C5 C13 85.4(2) . . . . ?
C1 O1 C5 C4 -37.5(3) . . . . ?
C1 O1 C5 C6 -154.50(18) . . . . ?
C3 C4 C5 O1 42.3(3) . . . . ?
C3 C4 C5 C13 -80.6(3) . . . . ?
C3 C4 C5 C6 156.90(19) . . . . ?
O1 C5 C6 C10 47.3(2) . . . . ?
C13 C5 C6 C10 166.18(19) . . . . ?
C4 C5 C6 C10 -72.3(2) . . . . ?
O1 C5 C6 C7 -73.8(2) . . . . ?
C13 C5 C6 C7 45.1(2) . . . . ?
C4 C5 C6 C7 166.59(18) . . . . ?
C10 C6 C7 C14 133.8(2) . . . . ?
C5 C6 C7 C14 -100.7(2) . . . . ?
C10 C6 C7 C8 7.5(2) . . . . ?
C5 C6 C7 C8 132.99(18) . . . . ?
C14 C7 C8 O3 -41.7(3) . . . . ?
C6 C7 C8 O3 85.4(2) . . . . ?
C14 C7 C8 C15 79.2(3) . . . . ?
C6 C7 C8 C15 -153.8(2) . . . . ?
C14 C7 C8 C9 -157.2(2) . . . . ?
C6 C7 C8 C9 -30.2(2) . . . . ?
O3 C8 C9 C10 -73.4(2) . . . . ?
C15 C8 C9 C10 163.3(2) . . . . ?
C7 C8 C9 C10 41.5(2) . . . . ?
C8 C9 C10 C6 -37.4(2) . . . . ?
C7 C6 C10 C9 18.2(2) . . . . ?
C5 C6 C10 C9 -108.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
