# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_13_0m
_database_code_depnum_ccdc_archive 'CCDC 2262466'
loop_
_audit_author_name
_audit_author_address
'Fei Xue'
;Nanjing forestry University
China
;
_audit_update_record             
;
2023-05-12 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O'
_chemical_formula_sum            'C15 H20 O'
_chemical_formula_weight         216.31
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.75930(10)
_cell_length_b                   16.2350(4)
_cell_length_c                   16.5153(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1276.09(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.58
_cell_measurement_theta_min      6.01
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1422 before and 0.0522 after correction. The Ratio of minimum to maximum transmission is 0.8965. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16119
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.575
_diffrn_reflns_theta_min         6.012
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2543
_reflns_number_total             2591
_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 (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         0.173
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.038
_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)+(0.0367P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0694
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C13(H13A,H13B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.5434(2) 0.77755(6) 0.47391(5) 0.0238(2) Uani 1 1 d . . . . .
C8 C 0.5222(3) 0.71869(8) 0.33388(7) 0.0222(3) Uani 1 1 d . . . . .
C9 C 0.3473(3) 0.73963(8) 0.27301(7) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.3714(3) 0.85594(8) 0.35546(8) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.5710(3) 0.79238(8) 0.38902(7) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.766521 0.812570 0.379091 0.026 Uiso 1 1 calc R . . . .
C1 C 0.2445(3) 0.82446(8) 0.28549(8) 0.0223(3) Uani 1 1 d . . . . .
C14 C 0.6582(3) 0.63682(8) 0.34908(8) 0.0259(3) Uani 1 1 d . . . . .
H14A H 0.844877 0.645801 0.373981 0.031 Uiso 1 1 calc R . . . .
H14B H 0.687278 0.608453 0.296685 0.031 Uiso 1 1 calc R . . . .
C2 C 0.0478(3) 0.87126(9) 0.24354(8) 0.0276(3) Uani 1 1 d . . . . .
H2 H -0.038499 0.850627 0.195804 0.033 Uiso 1 1 calc R . . . .
C5 C 0.3069(3) 0.93328(8) 0.38409(9) 0.0296(3) Uani 1 1 d . . . . .
H5 H 0.395686 0.954388 0.431244 0.036 Uiso 1 1 calc R . . . .
C10 C 0.2655(3) 0.68836(9) 0.20104(8) 0.0273(3) Uani 1 1 d . . . . .
H10A H 0.058762 0.689948 0.194704 0.033 Uiso 1 1 calc R . . . .
H10B H 0.320776 0.630443 0.210946 0.033 Uiso 1 1 calc R . . . .
C13 C 0.4831(4) 0.58145(9) 0.40457(9) 0.0332(3) Uani 1 1 d . . . . .
H13A H 0.474079 0.606662 0.459090 0.040 Uiso 1 1 calc R . . . .
H13B H 0.289066 0.578232 0.383211 0.040 Uiso 1 1 calc R . . . .
C3 C -0.0197(3) 0.94923(9) 0.27324(9) 0.0337(3) Uani 1 1 d . . . . .
H3 H -0.155513 0.981691 0.245682 0.040 Uiso 1 1 calc R . . . .
C11 C 0.4034(3) 0.71827(9) 0.12224(8) 0.0323(3) Uani 1 1 d . . . . .
H11A H 0.345369 0.775849 0.111755 0.039 Uiso 1 1 calc R . . . .
H11B H 0.610126 0.717626 0.128866 0.039 Uiso 1 1 calc R . . . .
C4 C 0.1077(4) 0.98005(9) 0.34217(9) 0.0362(4) Uani 1 1 d . . . . .
H4 H 0.059503 1.033445 0.361169 0.043 Uiso 1 1 calc R . . . .
C12 C 0.3240(4) 0.66518(10) 0.04973(9) 0.0410(4) Uani 1 1 d . . . . .
H12A H 0.415876 0.686675 0.001010 0.062 Uiso 1 1 calc GR . . . .
H12B H 0.119717 0.666353 0.042321 0.062 Uiso 1 1 calc GR . . . .
H12C H 0.385251 0.608364 0.059196 0.062 Uiso 1 1 calc GR . . . .
C15 C 0.6015(4) 0.49472(9) 0.41199(10) 0.0404(4) Uani 1 1 d . . . . .
H15A H 0.589694 0.466931 0.359427 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.492825 0.463775 0.452167 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.798409 0.497599 0.429163 0.061 Uiso 1 1 calc GR . . . .
H1 H 0.379(5) 0.7586(13) 0.4838(13) 0.050(6) Uiso 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
O1 C7 1.4287(15) . ?
O1 H1 0.86(2) . ?
C8 C9 1.3487(18) . ?
C8 C7 1.5214(18) . ?
C8 C14 1.4994(18) . ?
C9 C1 1.4761(18) . ?
C9 C10 1.5023(18) . ?
C6 C7 1.5082(18) . ?
C6 C1 1.4003(18) . ?
C6 C5 1.3764(19) . ?
C7 H7 1.0000 . ?
C1 C2 1.3904(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.5303(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.398(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5362(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C15 1.522(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.523(2) . ?
C4 H4 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C7 O1 H1 109.4(15) . . ?
C9 C8 C7 110.01(11) . . ?
C9 C8 C14 127.92(12) . . ?
C14 C8 C7 122.07(11) . . ?
C8 C9 C1 109.62(11) . . ?
C8 C9 C10 127.58(13) . . ?
C1 C9 C10 122.79(12) . . ?
C1 C6 C7 108.98(11) . . ?
C5 C6 C7 129.67(13) . . ?
C5 C6 C1 121.35(13) . . ?
O1 C7 C8 116.15(10) . . ?
O1 C7 C6 114.70(11) . . ?
O1 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C6 C7 C8 102.82(10) . . ?
C6 C7 H7 107.6 . . ?
C6 C1 C9 108.22(11) . . ?
C2 C1 C9 131.56(13) . . ?
C2 C1 C6 120.14(13) . . ?
C8 C14 H14A 109.1 . . ?
C8 C14 H14B 109.1 . . ?
C8 C14 C13 112.70(11) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.40(14) . . ?
C3 C2 H2 120.8 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.46(14) . . ?
C4 C5 H5 120.8 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C9 C10 C11 112.61(11) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C13 C14 112.96(13) . . ?
C15 C13 H13A 109.0 . . ?
C15 C13 H13B 109.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.09(14) . . ?
C4 C3 H3 119.5 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.41(12) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.55(14) . . ?
C3 C4 H4 119.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
