# 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_191031_fjj_2_073_0m
_database_code_depnum_ccdc_archive 'CCDC 2005327'
loop_
_audit_author_name
_audit_author_address
'Liu Jiyong'
;Zhejiang University
China
;
_audit_update_record             
;
2020-05-23 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34
_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      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                   13.1699(4)
_cell_length_b                   6.7473(2)
_cell_length_c                   16.9652(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.1300(10)
_cell_angle_gamma                90
_cell_volume                     1503.63(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5652
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1823 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12779
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_min         2.407
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2795
_reflns_number_total             3318
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.4536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1060
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.39611(7) 0.59833(15) 0.65427(6) 0.0399(3) Uani 1 1 d . . . . .
O2 O 0.05531(6) 0.05426(14) 0.81229(5) 0.0316(2) Uani 1 1 d . . . . .
O3 O 0.11076(7) -0.24045(15) 0.85838(6) 0.0404(2) Uani 1 1 d . . . . .
C1 C 0.30927(9) 0.9437(2) 0.59363(8) 0.0315(3) Uani 1 1 d . . . . .
H1 H 0.381184 0.929713 0.595638 0.038 Uiso 1 1 calc R . . . .
C2 C 0.26437(10) 1.1094(2) 0.55878(8) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.305849 1.207450 0.536950 0.041 Uiso 1 1 calc R . . . .
C3 C 0.15912(10) 1.13562(19) 0.55499(7) 0.0290(3) Uani 1 1 d . . . . .
C4 C 0.10078(9) 0.99024(19) 0.58811(8) 0.0307(3) Uani 1 1 d . . . . .
H4 H 0.028990 1.005914 0.586785 0.037 Uiso 1 1 calc R . . . .
C5 C 0.14527(9) 0.82274(19) 0.62306(7) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.103717 0.725242 0.645176 0.035 Uiso 1 1 calc R . . . .
C6 C 0.25075(9) 0.79607(18) 0.62605(7) 0.0255(3) Uani 1 1 d . . . . .
C7 C 0.30464(9) 0.61905(19) 0.66134(7) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.24554(8) 0.47044(18) 0.70295(7) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.173559 0.475013 0.693796 0.031 Uiso 1 1 calc R . . . .
C9 C 0.28420(8) 0.32935(18) 0.75256(7) 0.0248(2) Uani 1 1 d . . . . .
C10 C 0.21336(8) 0.18589(18) 0.78390(7) 0.0235(2) Uani 1 1 d . . . . .
C11 C 0.10060(8) 0.22628(19) 0.77876(8) 0.0283(3) Uani 1 1 d . . . . .
H11A H 0.085499 0.346852 0.809050 0.034 Uiso 1 1 calc R . . . .
H11B H 0.074387 0.244852 0.723089 0.034 Uiso 1 1 calc R . . . .
C12 C 0.13024(9) -0.07955(19) 0.83276(7) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.23022(8) 0.00619(18) 0.81682(7) 0.0241(2) Uani 1 1 d . . . . .
C14 C 0.32294(9) -0.11713(18) 0.83680(7) 0.0267(3) Uani 1 1 d . . . . .
H14A H 0.378382 -0.071559 0.804777 0.032 Uiso 1 1 calc R . . . .
H14B H 0.307650 -0.256721 0.822421 0.032 Uiso 1 1 calc R . . . .
C15 C 0.35966(9) -0.1073(2) 0.92426(8) 0.0327(3) Uani 1 1 d . . . . .
H15A H 0.377544 0.031338 0.938405 0.039 Uiso 1 1 calc R . . . .
H15B H 0.303743 -0.148982 0.956580 0.039 Uiso 1 1 calc R . . . .
C16 C 0.45160(10) -0.2390(2) 0.94332(9) 0.0408(3) Uani 1 1 d . . . . .
H16A H 0.507111 -0.198287 0.911403 0.061 Uiso 1 1 calc GR . . . .
H16B H 0.433403 -0.377181 0.931347 0.061 Uiso 1 1 calc GR . . . .
H16C H 0.473635 -0.226709 0.999524 0.061 Uiso 1 1 calc GR . . . .
C17 C 0.10973(11) 1.3161(2) 0.51705(9) 0.0395(3) Uani 1 1 d . . . . .
H17A H 0.090742 1.288674 0.461200 0.059 Uiso 1 1 calc GR . . . .
H17B H 0.157614 1.427423 0.521262 0.059 Uiso 1 1 calc GR . . . .
H17C H 0.048644 1.349885 0.543952 0.059 Uiso 1 1 calc GR . . . .
C18 C 0.39552(10) 0.3111(2) 0.77820(10) 0.0417(4) Uani 1 1 d . . . . .
H18A H 0.403251 0.259484 0.832301 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.427826 0.441661 0.776347 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.428027 0.220128 0.742663 0.063 Uiso 1 1 calc GR . . . .


_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 C7 1.2272(14) . ?
O2 C11 1.4406(15) . ?
O2 C12 1.3639(15) . ?
O3 C12 1.2039(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3778(19) . ?
C1 C6 1.3964(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3943(18) . ?
C3 C4 1.3894(17) . ?
C3 C17 1.5033(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3864(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3981(16) . ?
C6 C7 1.4924(17) . ?
C7 C8 1.4794(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3462(17) . ?
C9 C10 1.4702(16) . ?
C9 C18 1.5040(16) . ?
C10 C11 1.5062(15) . ?
C10 C13 1.3466(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4808(16) . ?
C13 C14 1.4963(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5285(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5181(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
C12 O2 C11 108.74(9) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.06(11) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.15(12) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C17 121.37(12) . . ?
C4 C3 C2 117.94(12) . . ?
C4 C3 C17 120.68(12) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.30(11) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.57(11) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.97(11) . . ?
C1 C6 C7 117.97(10) . . ?
C5 C6 C7 124.06(11) . . ?
O1 C7 C6 119.59(11) . . ?
O1 C7 C8 121.56(11) . . ?
C8 C7 C6 118.85(10) . . ?
C7 C8 H8 116.9 . . ?
C9 C8 C7 126.11(10) . . ?
C9 C8 H8 116.9 . . ?
C8 C9 C10 118.07(10) . . ?
C8 C9 C18 123.76(11) . . ?
C10 C9 C18 118.17(11) . . ?
C9 C10 C11 120.57(10) . . ?
C13 C10 C9 130.76(10) . . ?
C13 C10 C11 108.62(10) . . ?
O2 C11 C10 105.42(9) . . ?
O2 C11 H11A 110.7 . . ?
O2 C11 H11B 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
O2 C12 C13 109.36(10) . . ?
O3 C12 O2 121.32(11) . . ?
O3 C12 C13 129.32(12) . . ?
C10 C13 C12 107.77(10) . . ?
C10 C13 C14 134.60(11) . . ?
C12 C13 C14 117.60(11) . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.07(10) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 111.91(11) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
