# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_s
_audit_block_doi                 10.5517/ccdc.csd.cc288pt2
_database_code_depnum_ccdc_archive 'CCDC 2093734'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.1c02916 2022
loop_
_audit_author_name
_audit_author_address
'Chao Wang'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 O'
_chemical_formula_sum            'C17 H18 O'
_chemical_formula_weight         238.31
_chemical_absolute_configuration ad
_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 0.0181 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.5667(13)
_cell_length_b                   5.2499(6)
_cell_length_c                   12.1291(14)
_cell_angle_alpha                90
_cell_angle_beta                 117.369(3)
_cell_angle_gamma                90
_cell_volume                     654.08(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    205.0
_cell_measurement_theta_max      68.491
_cell_measurement_theta_min      4.104
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0771 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9493
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.485
_diffrn_reflns_theta_min         4.104
_diffrn_ambient_temperature      205.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2323
_reflns_number_total             2357
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.150
_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)+(0.0818P)²+0.1705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1646
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C00A(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C002(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00H), C00D(H00I), C00E(H00J), C00F(H00K),
 C00G(H00L), C00H(H00M), C00I(H00N)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
O001 O 0.9884(3) 0.3827(6) 0.9504(3) 0.1096(16) Uani 1 1 d . . . . .
H001 H 1.007103 0.259946 0.998742 0.164 Uiso 1 1 calc R U . . .
C002 C 0.6807(3) 0.1691(6) 0.6771(3) 0.0473(7) Uani 1 1 d . . . . .
H00A H 0.718063 0.016384 0.659521 0.057 Uiso 1 1 calc R U . . .
H00B H 0.593481 0.125664 0.665780 0.057 Uiso 1 1 calc R U . . .
C003 C 0.7654(3) 0.2503(6) 0.8113(3) 0.0512(8) Uani 1 1 d . . . . .
H003 H 0.770810 0.104619 0.865314 0.061 Uiso 1 1 calc R U . . .
C004 C 0.5733(4) 0.4394(6) 0.8326(3) 0.0579(9) Uani 1 1 d . . . . .
C005 C 0.7095(4) 0.4786(6) 0.8506(3) 0.0569(9) Uani 1 1 d . . . . .
H00C H 0.766425 0.514945 0.938476 0.068 Uiso 1 1 calc R U . . .
H00D H 0.710431 0.628303 0.802789 0.068 Uiso 1 1 calc R U . . .
C006 C 0.6698(3) 0.3770(8) 0.5865(3) 0.0564(9) Uani 1 1 d . . . . .
H00E H 0.638246 0.301337 0.503786 0.068 Uiso 1 1 calc R U . . .
H00F H 0.604522 0.500677 0.582474 0.068 Uiso 1 1 calc R U . . .
C007 C 0.4746(4) 0.6062(7) 0.7615(4) 0.0629(10) Uani 1 1 d . . . . .
H007 H 0.493410 0.745088 0.723458 0.076 Uiso 1 1 calc R U . . .
C008 C 0.7946(4) 0.5159(7) 0.6179(4) 0.0609(9) Uani 1 1 d . . . . .
C009 C 0.5422(5) 0.2357(8) 0.8882(4) 0.0754(13) Uani 1 1 d . . . . .
H009 H 0.607427 0.119497 0.937419 0.090 Uiso 1 1 calc R U . . .
C00A C 0.9008(3) 0.3007(7) 0.8271(4) 0.0701(12) Uani 1 1 d . . . . .
H00G H 0.934627 0.137889 0.812417 0.084 Uiso 1 1 calc R U . . .
C00B C 0.8001(6) 0.6794(9) 0.5291(5) 0.0842(14) Uani 1 1 d . . . . .
H00H H 0.728325 0.690378 0.449783 0.101 Uiso 1 1 calc R U . . .
C00C C 0.9023(3) 0.4923(6) 0.7345(5) 0.0668(11) Uani 1 1 d . . . . .
C00D C 0.3488(5) 0.5741(9) 0.7447(5) 0.0820(14) Uani 1 1 d . . . . .
H00I H 0.283389 0.690104 0.695632 0.098 Uiso 1 1 calc R U . . .
C00E C 1.0144(7) 0.8090(10) 0.6717(10) 0.128(3) Uani 1 1 d . . . . .
H00J H 1.087920 0.911182 0.690521 0.154 Uiso 1 1 calc R U . . .
C00F C 0.4175(7) 0.2028(9) 0.8720(5) 0.0953(18) Uani 1 1 d . . . . .
H00K H 0.398451 0.064405 0.910109 0.114 Uiso 1 1 calc R U . . .
C00G C 0.9079(9) 0.8224(11) 0.5560(9) 0.118(3) Uani 1 1 d . . . . .
H00L H 0.909757 0.931187 0.495251 0.142 Uiso 1 1 calc R U . . .
C00H C 1.0123(4) 0.6425(9) 0.7606(7) 0.102(2) Uani 1 1 d . . . . .
H00M H 1.085490 0.630997 0.838928 0.123 Uiso 1 1 calc R U . . .
C00I C 0.3196(6) 0.3712(9) 0.8001(6) 0.0958(18) Uani 1 1 d . . . . .
H00N H 0.234377 0.347902 0.789170 0.115 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
O001 H001 0.8300 . ?
O001 C00A 1.434(5) . ?
C002 H00A 0.9800 . ?
C002 H00B 0.9800 . ?
C002 C003 1.525(4) . ?
C002 C006 1.512(5) . ?
C003 H003 0.9900 . ?
C003 C005 1.538(5) . ?
C003 C00A 1.511(6) . ?
C004 C005 1.502(6) . ?
C004 C007 1.382(5) . ?
C004 C009 1.397(5) . ?
C005 H00C 0.9800 . ?
C005 H00D 0.9800 . ?
C006 H00E 0.9800 . ?
C006 H00F 0.9800 . ?
C006 C008 1.501(5) . ?
C007 H007 0.9400 . ?
C007 C00D 1.383(7) . ?
C008 C00B 1.402(6) . ?
C008 C00C 1.395(6) . ?
C009 H009 0.9400 . ?
C009 C00F 1.374(8) . ?
C00A H00G 0.9900 . ?
C00A C00C 1.515(6) . ?
C00B H00H 0.9400 . ?
C00B C00G 1.360(9) . ?
C00C C00H 1.404(6) . ?
C00D H00I 0.9400 . ?
C00D C00I 1.382(7) . ?
C00E H00J 0.9400 . ?
C00E C00G 1.379(11) . ?
C00E C00H 1.397(11) . ?
C00F H00K 0.9400 . ?
C00F C00I 1.384(8) . ?
C00G H00L 0.9400 . ?
C00H H00M 0.9400 . ?
C00I H00N 0.9400 . ?

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
C00A O001 H001 109.5 . . ?
H00A C002 H00B 107.9 . . ?
C003 C002 H00A 109.2 . . ?
C003 C002 H00B 109.2 . . ?
C006 C002 H00A 109.2 . . ?
C006 C002 H00B 109.2 . . ?
C006 C002 C003 111.8(3) . . ?
C002 C003 H003 107.7 . . ?
C002 C003 C005 113.2(3) . . ?
C005 C003 H003 107.7 . . ?
C00A C003 C002 107.7(3) . . ?
C00A C003 H003 107.7 . . ?
C00A C003 C005 112.5(3) . . ?
C007 C004 C005 120.9(3) . . ?
C007 C004 C009 117.7(4) . . ?
C009 C004 C005 121.4(3) . . ?
C003 C005 H00C 108.7 . . ?
C003 C005 H00D 108.7 . . ?
C004 C005 C003 114.2(3) . . ?
C004 C005 H00C 108.7 . . ?
C004 C005 H00D 108.7 . . ?
H00C C005 H00D 107.6 . . ?
C002 C006 H00E 108.6 . . ?
C002 C006 H00F 108.6 . . ?
H00E C006 H00F 107.6 . . ?
C008 C006 C002 114.6(3) . . ?
C008 C006 H00E 108.6 . . ?
C008 C006 H00F 108.6 . . ?
C004 C007 H007 119.1 . . ?
C004 C007 C00D 121.7(4) . . ?
C00D C007 H007 119.1 . . ?
C00B C008 C006 118.7(4) . . ?
C00C C008 C006 121.4(3) . . ?
C00C C008 C00B 119.8(4) . . ?
C004 C009 H009 119.5 . . ?
C00F C009 C004 120.9(4) . . ?
C00F C009 H009 119.5 . . ?
O001 C00A C003 112.3(4) . . ?
O001 C00A H00G 107.4 . . ?
O001 C00A C00C 109.3(3) . . ?
C003 C00A H00G 107.4 . . ?
C003 C00A C00C 112.8(3) . . ?
C00C C00A H00G 107.4 . . ?
C008 C00B H00H 119.5 . . ?
C00G C00B C008 121.0(6) . . ?
C00G C00B H00H 119.5 . . ?
C008 C00C C00A 120.0(3) . . ?
C008 C00C C00H 118.3(5) . . ?
C00H C00C C00A 121.6(5) . . ?
C007 C00D H00I 120.1 . . ?
C00I C00D C007 119.9(5) . . ?
C00I C00D H00I 120.1 . . ?
C00G C00E H00J 120.2 . . ?
C00G C00E C00H 119.5(5) . . ?
C00H C00E H00J 120.2 . . ?
C009 C00F H00K 119.6 . . ?
C009 C00F C00I 120.7(4) . . ?
C00I C00F H00K 119.6 . . ?
C00B C00G C00E 120.5(6) . . ?
C00B C00G H00L 119.7 . . ?
C00E C00G H00L 119.7 . . ?
C00C C00H H00M 119.6 . . ?
C00E C00H C00C 120.9(6) . . ?
C00E C00H H00M 119.6 . . ?
C00D C00I C00F 119.1(5) . . ?
C00D C00I H00N 120.5 . . ?
C00F C00I H00N 120.5 . . ?

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
O001 C00A C00C C008 -154.6(4) . . . . ?
O001 C00A C00C C00H 27.8(5) . . . . ?
C002 C003 C005 C004 55.8(4) . . . . ?
C002 C003 C00A O001 179.1(3) . . . . ?
C002 C003 C00A C00C 55.0(4) . . . . ?
C002 C006 C008 C00B 168.8(3) . . . . ?
C002 C006 C008 C00C -13.5(5) . . . . ?
C003 C002 C006 C008 41.4(4) . . . . ?
C003 C00A C00C C008 -28.9(5) . . . . ?
C003 C00A C00C C00H 153.5(4) . . . . ?
C004 C007 C00D C00I 0.1(7) . . . . ?
C004 C009 C00F C00I -0.1(7) . . . . ?
C005 C003 C00A O001 53.7(4) . . . . ?
C005 C003 C00A C00C -70.4(4) . . . . ?
C005 C004 C007 C00D -179.5(4) . . . . ?
C005 C004 C009 C00F 179.5(4) . . . . ?
C006 C002 C003 C005 62.8(4) . . . . ?
C006 C002 C003 C00A -62.2(3) . . . . ?
C006 C008 C00B C00G 175.6(4) . . . . ?
C006 C008 C00C C00A 7.2(5) . . . . ?
C006 C008 C00C C00H -175.2(4) . . . . ?
C007 C004 C005 C003 -123.6(3) . . . . ?
C007 C004 C009 C00F 0.2(5) . . . . ?
C007 C00D C00I C00F 0.0(7) . . . . ?
C008 C00B C00G C00E 0.1(7) . . . . ?
C008 C00C C00H C00E -0.8(6) . . . . ?
C009 C004 C005 C003 57.1(4) . . . . ?
C009 C004 C007 C00D -0.3(5) . . . . ?
C009 C00F C00I C00D -0.1(7) . . . . ?
C00A C003 C005 C004 178.2(3) . . . . ?
C00A C00C C00H C00E 176.7(4) . . . . ?
C00B C008 C00C C00A -175.2(3) . . . . ?
C00B C008 C00C C00H 2.4(5) . . . . ?
C00C C008 C00B C00G -2.1(6) . . . . ?
C00G C00E C00H C00C -1.2(7) . . . . ?
C00H C00E C00G C00B 1.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
