# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cu_190522c_0m
_database_code_depnum_ccdc_archive 'CCDC 2058189'
loop_
_audit_author_name
_audit_author_address
'wangqing kong'
;wuhan university
China
;
_audit_update_record             
;
2021-01-23 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8774(4)
_cell_length_b                   11.4152(4)
_cell_length_c                   13.2381(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.989(2)
_cell_angle_gamma                90
_cell_volume                     1334.19(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.40
_cell_measurement_theta_min      5.01
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7918
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        64.990
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_min         5.009
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1919
_reflns_number_total             2166
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0102(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.037
_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)+(0.0424P)²+0.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0901
_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), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7) 
2.c Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_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
C1 C 0.37792(16) 0.68748(12) 0.07660(11) 0.0421(3) Uani 1 1 d . . . . .
C2 C 0.26852(16) 0.76102(12) 0.11009(11) 0.0452(4) Uani 1 1 d . . . . .
H2A H 0.2243 0.7418 0.1686 0.054 Uiso 1 1 calc R . . . .
C3 C 0.22452(18) 0.86204(12) 0.05788(12) 0.0504(4) Uani 1 1 d . . . . .
H3 H 0.1520 0.9105 0.0820 0.060 Uiso 1 1 calc R . . . .
C4 C 0.28692(19) 0.89172(14) -0.02956(13) 0.0561(4) Uani 1 1 d . . . . .
H4 H 0.2564 0.9596 -0.0648 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3955(2) 0.81962(15) -0.06443(13) 0.0607(4) Uani 1 1 d . . . . .
H5 H 0.4378 0.8387 -0.1237 0.073 Uiso 1 1 calc R . . . .
C6 C 0.44108(17) 0.71941(14) -0.01153(12) 0.0533(4) Uani 1 1 d . . . . .
H6 H 0.5154 0.6723 -0.0351 0.064 Uiso 1 1 calc R . . . .
C7 C 0.43165(16) 0.58233(12) 0.13435(11) 0.0453(3) Uani 1 1 d . . . . .
H7 H 0.5356 0.5693 0.1410 0.054 Uiso 1 1 calc R . . . .
C8 C 0.34814(15) 0.50420(11) 0.17786(10) 0.0392(3) Uani 1 1 d . . . . .
C9 C 0.17848(14) 0.50035(11) 0.16628(9) 0.0368(3) Uani 1 1 d . . . . .
H9A H 0.1407 0.5463 0.1074 0.044 Uiso 1 1 calc R . . . .
H9B H 0.1415 0.5359 0.2255 0.044 Uiso 1 1 calc R . . . .
C10 C 0.11627(15) 0.37574(11) 0.15394(9) 0.0350(3) Uani 1 1 d . . . . .
C11 C 0.19727(17) 0.28930(12) 0.23079(10) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.42070(18) 0.41072(12) 0.24643(11) 0.0496(4) Uani 1 1 d . . . . .
H12A H 0.5282 0.4078 0.2389 0.060 Uiso 1 1 calc R . . . .
H12B H 0.4095 0.4311 0.3164 0.060 Uiso 1 1 calc R . . . .
C13 C 0.15723(18) 0.16841(12) 0.18763(11) 0.0488(4) Uani 1 1 d . . . . .
H13A H 0.0570 0.1447 0.2026 0.059 Uiso 1 1 calc R . . . .
H13B H 0.2304 0.1103 0.2147 0.059 Uiso 1 1 calc R . . . .
C14 C 0.16255(18) 0.18475(12) 0.07366(11) 0.0453(4) Uani 1 1 d . . . . .
H14A H 0.2580 0.1567 0.0532 0.054 Uiso 1 1 calc R . . . .
H14B H 0.0804 0.1425 0.0356 0.054 Uiso 1 1 calc R . . . .
C15 C 0.14626(15) 0.31539(11) 0.05562(9) 0.0357(3) Uani 1 1 d . . . . .
C16 C -0.05618(16) 0.37646(13) 0.15702(12) 0.0495(4) Uani 1 1 d . . . . .
H16A H -0.1012 0.4328 0.1092 0.074 Uiso 1 1 calc GR . . . .
H16B H -0.0790 0.3969 0.2241 0.074 Uiso 1 1 calc GR . . . .
H16C H -0.0961 0.3001 0.1397 0.074 Uiso 1 1 calc GR . . . .
O1 O 0.35612(11) 0.29713(8) 0.22509(7) 0.0449(3) Uani 1 1 d . . . . .
O2 O 0.15853(15) 0.31307(10) 0.32814(7) 0.0628(3) Uani 1 1 d . . . . .
H2 H 0.1727 0.2544 0.3637 0.094 Uiso 1 1 calc GR . . . .
O3 O 0.15508(12) 0.36371(9) -0.02488(7) 0.0500(3) Uani 1 1 d . . . . .


_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
C1 C2 1.391(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.475(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3288(19) . ?
C8 C9 1.4986(19) . ?
C8 C12 1.5019(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5284(17) . ?
C10 C11 1.5405(18) . ?
C10 C15 1.5206(17) . ?
C10 C16 1.5357(19) . ?
C11 C13 1.522(2) . ?
C11 O1 1.4228(17) . ?
C11 O2 1.3947(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 O1 1.4339(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.526(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5148(18) . ?
C15 O3 1.2097(15) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O2 H2 0.8200 . ?

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
C2 C1 C6 117.65(13) . . ?
C2 C1 C7 121.65(13) . . ?
C6 C1 C7 120.64(13) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.02(14) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.61(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.33(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.13(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.26(15) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 116.4 . . ?
C8 C7 C1 127.29(13) . . ?
C8 C7 H7 116.4 . . ?
C7 C8 C9 125.14(12) . . ?
C7 C8 C12 121.02(13) . . ?
C9 C8 C12 113.83(12) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C8 C9 C10 112.73(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 C11 112.77(11) . . ?
C9 C10 C16 110.01(10) . . ?
C15 C10 C9 114.80(10) . . ?
C15 C10 C11 99.42(10) . . ?
C15 C10 C16 106.81(11) . . ?
C16 C10 C11 112.57(11) . . ?
C13 C11 C10 104.97(11) . . ?
O1 C11 C10 108.76(10) . . ?
O1 C11 C13 103.36(11) . . ?
O2 C11 C10 110.03(11) . . ?
O2 C11 C13 116.94(12) . . ?
O2 C11 O1 112.22(11) . . ?
C8 C12 H12A 109.1 . . ?
C8 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O1 C12 C8 112.70(11) . . ?
O1 C12 H12A 109.1 . . ?
O1 C12 H12B 109.1 . . ?
C11 C13 H13A 111.1 . . ?
C11 C13 H13B 111.1 . . ?
C11 C13 C14 103.32(10) . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C15 C14 C13 105.31(11) . . ?
C15 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
C14 C15 C10 109.48(10) . . ?
O3 C15 C10 125.50(11) . . ?
O3 C15 C14 125.02(12) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O1 C12 115.12(11) . . ?
C11 O2 H2 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 2.02 2.8055(14) 161.1 4_566

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
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C7 C8 C9 7.6(2) . . . . ?
C1 C7 C8 C12 -171.39(13) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C7 C8 43.6(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C7 C8 -139.49(16) . . . . ?
C7 C1 C2 C3 176.90(12) . . . . ?
C7 C1 C6 C5 -177.83(14) . . . . ?
C7 C8 C9 C10 138.81(13) . . . . ?
C7 C8 C12 O1 -134.31(14) . . . . ?
C8 C9 C10 C11 45.77(14) . . . . ?
C8 C9 C10 C15 -67.16(14) . . . . ?
C8 C9 C10 C16 172.35(11) . . . . ?
C8 C12 O1 C11 -57.23(16) . . . . ?
C9 C8 C12 O1 46.62(17) . . . . ?
C9 C10 C11 C13 -163.01(11) . . . . ?
C9 C10 C11 O1 -52.93(14) . . . . ?
C9 C10 C11 O2 70.36(15) . . . . ?
C9 C10 C15 C14 148.79(12) . . . . ?
C9 C10 C15 O3 -31.56(18) . . . . ?
C10 C11 C13 C14 39.02(14) . . . . ?
C10 C11 O1 C12 59.42(13) . . . . ?
C11 C10 C15 C14 28.20(14) . . . . ?
C11 C10 C15 O3 -152.15(13) . . . . ?
C11 C13 C14 C15 -20.39(15) . . . . ?
C12 C8 C9 C10 -42.16(15) . . . . ?
C13 C11 O1 C12 170.59(10) . . . . ?
C13 C14 C15 C10 -5.40(16) . . . . ?
C13 C14 C15 O3 174.95(13) . . . . ?
C15 C10 C11 C13 -40.95(13) . . . . ?
C15 C10 C11 O1 69.14(12) . . . . ?
C15 C10 C11 O2 -167.57(11) . . . . ?
C16 C10 C11 C13 71.79(14) . . . . ?
C16 C10 C11 O1 -178.13(10) . . . . ?
C16 C10 C11 O2 -54.84(15) . . . . ?
C16 C10 C15 C14 -88.97(13) . . . . ?
C16 C10 C15 O3 90.69(15) . . . . ?
O1 C11 C13 C14 -74.91(12) . . . . ?
O2 C11 C13 C14 161.27(12) . . . . ?
O2 C11 O1 C12 -62.55(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
