# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_mo_210909a_0m
_database_code_depnum_ccdc_archive 'CCDC 2151471'
loop_
_audit_author_name
_audit_author_address
'shanghua xu'
;Central China Normal University
China
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_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         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35
_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                   5.7272(12)
_cell_length_b                   7.6083(16)
_cell_length_c                   18.734(4)
_cell_angle_alpha                79.036(3)
_cell_angle_beta                 82.382(3)
_cell_angle_gamma                87.161(4)
_cell_volume                     794.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      29.71
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5749
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.728
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                1930
_reflns_number_total             2900
_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         0.567
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.030
_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)+(0.0768P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1660
_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 Ternary CH refined with riding coordinates: 
 C11(H11) 
2.b Secondary CH2 refined with riding coordinates: 
 C9(H9A,H9B), C10(H10A,H10B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C3(H3A), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), 
 C17(H17), C18(H18), C19(H19) 
2.d Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_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 0.4201(3) 0.2859(2) 1.38662(8) 0.0525(5) Uani 1 1 d . . . . .
O2 O 0.2816(3) 0.2253(3) 1.06467(9) 0.0614(5) Uani 1 1 d . . . . .
O3 O 1.1082(4) 0.1908(4) 0.93266(10) 0.0992(9) Uani 1 1 d . . . . .
H3 H 1.1506 0.2213 0.9685 0.149 Uiso 1 1 calc GR . . . .
C1 C 0.6070(5) 0.3586(4) 1.41384(13) 0.0647(8) Uani 1 1 d . . . . .
H1A H 0.6267 0.4815 1.3903 0.097 Uiso 1 1 calc GR . . . .
H1B H 0.7502 0.2916 1.4038 0.097 Uiso 1 1 calc GR . . . .
H1C H 0.5702 0.3519 1.4658 0.097 Uiso 1 1 calc GR . . . .
C2 C 0.4435(4) 0.2839(3) 1.31326(11) 0.0390(5) Uani 1 1 d . . . . .
C3 C 0.2621(4) 0.2051(3) 1.28903(12) 0.0436(6) Uani 1 1 d . . . . .
H3A H 0.1349 0.1586 1.3222 0.052 Uiso 1 1 calc R . . . .
C4 C 0.2701(4) 0.1959(3) 1.21655(11) 0.0406(5) Uani 1 1 d . . . . .
H4 H 0.1462 0.1452 1.2008 0.049 Uiso 1 1 calc R . . . .
C5 C 0.4621(4) 0.2616(3) 1.16562(11) 0.0359(5) Uani 1 1 d . . . . .
C6 C 0.6419(4) 0.3381(3) 1.19126(11) 0.0439(6) Uani 1 1 d . . . . .
H6 H 0.7720 0.3812 1.1586 0.053 Uiso 1 1 calc R . . . .
C7 C 0.6327(4) 0.3519(3) 1.26395(11) 0.0444(6) Uani 1 1 d . . . . .
H7 H 0.7531 0.4067 1.2796 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4638(4) 0.2504(3) 1.08742(11) 0.0387(5) Uani 1 1 d . . . . .
C9 C 0.6945(4) 0.2706(4) 1.03803(12) 0.0479(6) Uani 1 1 d . . . . .
H9A H 0.8067 0.1830 1.0594 0.058 Uiso 1 1 calc R . . . .
H9B H 0.7537 0.3883 1.0373 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6878(4) 0.2490(3) 0.95959(11) 0.0436(6) Uani 1 1 d . . . . .
H10A H 0.6506 0.1263 0.9592 0.052 Uiso 1 1 calc R . . . .
H10B H 0.5632 0.3261 0.9394 0.052 Uiso 1 1 calc R . . . .
C11 C 0.9176(4) 0.2944(4) 0.91176(13) 0.0553(7) Uani 1 1 d . . . . .
H11 H 0.9512 0.4176 0.9150 0.066 Uiso 1 1 calc R . . . .
C12 C 0.9050(4) 0.2933(4) 0.83250(12) 0.0503(6) Uani 1 1 d . . . . .
H12 H 0.7756 0.3505 0.8120 0.060 Uiso 1 1 calc R . . . .
C13 C 1.0631(4) 0.2177(3) 0.78979(12) 0.0428(6) Uani 1 1 d . . . . .
H13 H 1.1878 0.1575 0.8119 0.051 Uiso 1 1 calc R . . . .
C14 C 1.0674(4) 0.2163(3) 0.71129(11) 0.0395(5) Uani 1 1 d . . . . .
C15 C 0.8931(4) 0.2976(4) 0.67033(13) 0.0565(7) Uani 1 1 d . . . . .
H15 H 0.7647 0.3547 0.6929 0.068 Uiso 1 1 calc R . . . .
C16 C 0.9086(5) 0.2946(5) 0.59682(14) 0.0716(9) Uani 1 1 d . . . . .
H16 H 0.7912 0.3509 0.5701 0.086 Uiso 1 1 calc R . . . .
C17 C 1.0948(5) 0.2095(4) 0.56205(14) 0.0654(8) Uani 1 1 d . . . . .
H17 H 1.1031 0.2074 0.5123 0.078 Uiso 1 1 calc R . . . .
C18 C 1.2665(5) 0.1287(4) 0.60115(14) 0.0595(7) Uani 1 1 d . . . . .
H18 H 1.3930 0.0706 0.5781 0.071 Uiso 1 1 calc R . . . .
C19 C 1.2542(4) 0.1324(3) 0.67535(12) 0.0495(6) Uani 1 1 d . . . . .
H19 H 1.3739 0.0774 0.7014 0.059 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 1.422(3) . ?
O1 C2 1.366(2) . ?
O2 C8 1.215(3) . ?
O3 H3 0.8200 . ?
O3 C11 1.370(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.391(3) . ?
C2 C7 1.379(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(3) . ?
C5 C6 1.388(3) . ?
C5 C8 1.482(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.498(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.313(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.470(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9300 . ?

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 O1 C1 117.45(18) . . ?
C11 O3 H3 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.90(19) . . ?
O1 C2 C7 124.3(2) . . ?
C7 C2 C3 119.76(19) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 C2 120.24(19) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.04(19) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C8 119.50(18) . . ?
C6 C5 C4 117.63(19) . . ?
C6 C5 C8 122.86(19) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.73(19) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
O2 C8 C5 119.87(19) . . ?
O2 C8 C9 121.66(19) . . ?
C5 C8 C9 118.47(18) . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C8 C9 C10 116.15(18) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.61(18) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
O3 C11 C10 115.2(2) . . ?
O3 C11 H11 106.5 . . ?
O3 C11 C12 108.4(2) . . ?
C10 C11 H11 106.5 . . ?
C12 C11 C10 113.1(2) . . ?
C12 C11 H11 106.5 . . ?
C11 C12 H12 117.6 . . ?
C13 C12 C11 124.8(2) . . ?
C13 C12 H12 117.6 . . ?
C12 C13 H13 116.0 . . ?
C12 C13 C14 128.0(2) . . ?
C14 C13 H13 116.0 . . ?
C15 C14 C13 123.3(2) . . ?
C19 C14 C13 119.2(2) . . ?
C19 C14 C15 117.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 121.2(2) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?

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
O3 H3 O2 0.82 2.05 2.845(2) 164.4 1_655

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
O1 C2 C3 C4 -179.7(2) . . . . ?
O1 C2 C7 C6 178.1(2) . . . . ?
O2 C8 C9 C10 -2.8(4) . . . . ?
O3 C11 C12 C13 -5.3(4) . . . . ?
C1 O1 C2 C3 177.4(2) . . . . ?
C1 O1 C2 C7 -1.9(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C2 C7 C6 -1.2(4) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 -179.6(2) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C8 O2 17.4(3) . . . . ?
C4 C5 C8 C9 -162.6(2) . . . . ?
C5 C6 C7 C2 1.8(4) . . . . ?
C5 C8 C9 C10 177.1(2) . . . . ?
C6 C5 C8 O2 -161.4(2) . . . . ?
C6 C5 C8 C9 18.7(3) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C8 C5 C6 C7 177.9(2) . . . . ?
C8 C9 C10 C11 172.7(2) . . . . ?
C9 C10 C11 O3 60.9(3) . . . . ?
C9 C10 C11 C12 -173.6(2) . . . . ?
C10 C11 C12 C13 -134.3(3) . . . . ?
C11 C12 C13 C14 -177.7(2) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C12 C13 C14 C19 178.3(2) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C13 C14 C19 C18 -179.6(2) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C14 0.6(4) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
