# 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_127-3
_database_code_depnum_ccdc_archive 'CCDC 2084815'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3313(17)
_cell_length_b                   8.8068(15)
_cell_length_c                   10.2625(15)
_cell_angle_alpha                77.537(14)
_cell_angle_beta                 72.055(16)
_cell_angle_gamma                75.300(16)
_cell_volume                     685.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1770
_cell_measurement_theta_min      3.1650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4266
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.110
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  21.00   1.00    2.00    --  -11.27 -77.00 120.00   98
  2  ω    -57.00  36.00   1.00    2.00    --   11.90 -57.00-120.00   93
  3  ω    -16.00  83.00   1.00    2.00    --   11.90  57.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205759000
_diffrn_orient_matrix_UB_12      -0.0493727000
_diffrn_orient_matrix_UB_13      -0.0514824000
_diffrn_orient_matrix_UB_21      -0.0880242000
_diffrn_orient_matrix_UB_22      0.0160740000
_diffrn_orient_matrix_UB_23      0.0005210000
_diffrn_orient_matrix_UB_31      0.0132681000
_diffrn_orient_matrix_UB_32      0.0663004000
_diffrn_orient_matrix_UB_33      -0.0524220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1561
_reflns_number_total             2399
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0832
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2123
_refine_ls_wR_factor_ref         0.2471
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C2(H2), C15(H15), C7(H7), C3(H3), C6(H6), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O2 O 0.6230(2) 0.1089(2) 0.84322(18) 0.0273(6) Uani 1 1 d . . . . .
O1 O 0.3356(2) 0.1832(2) 0.96336(19) 0.0301(6) Uani 1 1 d . . . . .
H1 H 0.323697 0.099877 1.015851 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6916(4) 0.2317(3) 0.8531(3) 0.0245(7) Uani 1 1 d . . . . .
C12 C 0.6170(4) 0.3921(3) 0.8249(3) 0.0256(7) Uani 1 1 d . . . . .
C10 C 0.4462(4) 0.1496(3) 0.8339(3) 0.0273(7) Uani 1 1 d . . . . .
C8 C 0.4659(4) 0.4357(3) 0.7681(3) 0.0260(7) Uani 1 1 d . . . . .
C16 C 0.8456(4) 0.1863(3) 0.8919(3) 0.0290(7) Uani 1 1 d . . . . .
H16 H 0.894250 0.079071 0.909313 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7007(4) 0.5024(3) 0.8418(3) 0.0303(7) Uani 1 1 d . . . . .
H13 H 0.652908 0.609958 0.825556 0.036 Uiso 1 1 calc R U . . .
C1 C 0.2379(4) 0.6469(3) 0.6817(3) 0.0277(7) Uani 1 1 d . . . . .
C2 C 0.2306(4) 0.5894(3) 0.5677(3) 0.0300(8) Uani 1 1 d . . . . .
H2 H 0.317463 0.507244 0.532327 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9255(4) 0.2980(3) 0.9044(3) 0.0323(8) Uani 1 1 d . . . . .
H15 H 1.029372 0.267119 0.928130 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3769(4) 0.5856(3) 0.7499(3) 0.0281(7) Uani 1 1 d . . . . .
H7 H 0.407564 0.659628 0.785141 0.034 Uiso 1 1 calc R U . . .
C4 C -0.0358(4) 0.7728(3) 0.5559(3) 0.0318(8) Uani 1 1 d . . . . .
C9 C 0.4224(4) 0.2982(3) 0.7297(3) 0.0290(7) Uani 1 1 d . . . . .
H9A H 0.495780 0.277691 0.638882 0.035 Uiso 1 1 calc R U . . .
H9B H 0.303882 0.325800 0.724821 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0968(4) 0.6519(3) 0.5061(3) 0.0301(7) Uani 1 1 d . . . . .
H3 H 0.096263 0.611623 0.429681 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1073(4) 0.7739(3) 0.7274(3) 0.0297(7) Uani 1 1 d . . . . .
H6 H 0.110743 0.818815 0.800418 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4186(4) 0.0062(3) 0.7930(3) 0.0322(8) Uani 1 1 d . . . . .
H17A H 0.492902 -0.009323 0.702493 0.048 Uiso 1 1 calc R U . . .
H17B H 0.300756 0.022072 0.791583 0.048 Uiso 1 1 calc R U . . .
H17C H 0.444485 -0.085692 0.858658 0.048 Uiso 1 1 calc R U . . .
C5 C -0.0274(4) 0.8345(3) 0.6664(3) 0.0336(8) Uani 1 1 d . . . . .
H5 H -0.113613 0.918029 0.700124 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8510(4) 0.4576(4) 0.8815(3) 0.0337(8) Uani 1 1 d . . . . .
H14 H 0.902695 0.534060 0.892963 0.040 Uiso 1 1 calc R U . . .
C18 C -0.1848(4) 0.8348(4) 0.4915(3) 0.0416(9) Uani 1 1 d . . . . .
H18A H -0.145814 0.823714 0.395045 0.062 Uiso 1 1 calc R U . . .
H18B H -0.229395 0.944843 0.500792 0.062 Uiso 1 1 calc R U . . .
H18C H -0.273722 0.775352 0.537580 0.062 Uiso 1 1 calc R U . . .


_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
O2 C11 1.380(3) . ?
O2 C10 1.453(3) . ?
O1 H1 0.8200 . ?
O1 C10 1.406(3) . ?
C11 C12 1.398(4) . ?
C11 C16 1.396(4) . ?
C12 C8 1.477(4) . ?
C12 C13 1.397(4) . ?
C10 C9 1.513(4) . ?
C10 C17 1.504(4) . ?
C8 C7 1.345(4) . ?
C8 C9 1.506(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C1 C2 1.394(4) . ?
C1 C7 1.463(4) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C7 H7 0.9300 . ?
C4 C3 1.380(4) . ?
C4 C5 1.386(4) . ?
C4 C18 1.510(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.387(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C11 O2 C10 116.43(19) . . ?
C10 O1 H1 109.5 . . ?
O2 C11 C12 123.7(3) . . ?
O2 C11 C16 115.5(2) . . ?
C16 C11 C12 120.8(3) . . ?
C11 C12 C8 119.1(3) . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 C8 123.8(2) . . ?
O2 C10 C9 109.6(2) . . ?
O2 C10 C17 105.1(2) . . ?
O1 C10 O2 108.9(2) . . ?
O1 C10 C9 107.6(2) . . ?
O1 C10 C17 112.4(2) . . ?
C17 C10 C9 113.2(2) . . ?
C12 C8 C9 114.1(2) . . ?
C7 C8 C12 122.9(3) . . ?
C7 C8 C9 122.9(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13 118.8 . . ?
C2 C1 C7 123.5(2) . . ?
C2 C1 C6 116.8(3) . . ?
C6 C1 C7 119.6(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C8 C7 C1 128.3(3) . . ?
C8 C7 H7 115.9 . . ?
C1 C7 H7 115.9 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C18 120.7(3) . . ?
C5 C4 C18 121.5(3) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 C10 111.6(2) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 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
O2 C11 C12 C8 -6.2(4) . . . . ?
O2 C11 C12 C13 179.0(2) . . . . ?
O2 C11 C16 C15 179.7(2) . . . . ?
O2 C10 C9 C8 -58.2(3) . . . . ?
O1 C10 C9 C8 60.1(3) . . . . ?
C11 O2 C10 O1 -71.5(3) . . . . ?
C11 O2 C10 C9 45.9(3) . . . . ?
C11 O2 C10 C17 167.8(2) . . . . ?
C11 C12 C8 C7 173.8(3) . . . . ?
C11 C12 C8 C9 -7.5(4) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C11 C16 C15 C14 1.5(4) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C8 C7 C1 172.8(3) . . . . ?
C12 C8 C9 C10 39.2(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C10 O2 C11 C12 -14.4(4) . . . . ?
C10 O2 C11 C16 166.7(2) . . . . ?
C8 C12 C13 C14 -173.2(2) . . . . ?
C16 C11 C12 C8 172.7(2) . . . . ?
C16 C11 C12 C13 -2.0(4) . . . . ?
C16 C15 C14 C13 -2.2(4) . . . . ?
C13 C12 C8 C7 -11.9(4) . . . . ?
C13 C12 C8 C9 166.9(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C2 C1 C7 C8 -34.4(4) . . . . ?
C2 C1 C6 C5 3.0(4) . . . . ?
C7 C8 C9 C10 -142.1(3) . . . . ?
C7 C1 C2 C3 -179.7(2) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C9 C8 C7 C1 -5.9(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C6 C1 C2 C3 -2.1(4) . . . . ?
C6 C1 C7 C8 148.2(3) . . . . ?
C17 C10 C9 C8 -175.1(2) . . . . ?
C5 C4 C3 C2 2.6(4) . . . . ?
C18 C4 C3 C2 -177.3(3) . . . . ?
C18 C4 C5 C6 178.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.499
_oxdiff_exptl_absorpt_empirical_full_min 0.436
