# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2350852'
loop_
_audit_author_name
_audit_author_address
'Qiang Zhao'
;Nanyang Normal University
China
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_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                   11.2312(4)
_cell_length_b                   14.7726(6)
_cell_length_c                   8.2671(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.0620(10)
_cell_angle_gamma                90
_cell_volume                     1296.42(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5804
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.9233.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1867
_reflns_number_total             2275
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.050
_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)+(0.0614P)²+0.3124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C9(H9), C12(H12), C14(H14), C13(H13)
;
_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
O2 O 0.42763(11) 0.40188(9) 0.19742(16) 0.0631(4) Uani 1 1 d . . . . .
O1 O 0.22220(13) 0.33300(10) 0.58265(19) 0.0752(4) Uani 1 1 d . . . . .
C16 C 0.17032(14) 0.53415(11) 0.1093(2) 0.0468(4) Uani 1 1 d . . . . .
C5 C 0.32718(15) 0.37087(10) 0.3883(2) 0.0468(4) Uani 1 1 d . . . . .
C7 C 0.14511(14) 0.47289(11) 0.22394(19) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.21990(15) 0.38690(11) 0.2253(2) 0.0469(4) Uani 1 1 d . . . . .
H6 H 0.165095 0.333761 0.191792 0.056 Uiso 1 1 calc R U . . .
C11 C 0.11444(16) 0.62024(11) 0.0735(2) 0.0545(4) Uani 1 1 d . . . . .
C15 C 0.25438(16) 0.50026(12) 0.0308(2) 0.0538(4) Uani 1 1 d . . . . .
C4 C 0.43704(16) 0.38132(11) 0.3604(2) 0.0512(4) Uani 1 1 d . . . . .
C00A C 0.32111(17) 0.34920(11) 0.5561(2) 0.0549(4) Uani 1 1 d . . . . .
C17 C 0.29188(16) 0.40621(12) 0.0972(2) 0.0548(4) Uani 1 1 d . . . . .
H17 H 0.269875 0.361942 0.003775 0.066 Uiso 1 1 calc R U . . .
C8 C 0.06393(16) 0.49762(13) 0.3064(2) 0.0560(4) Uani 1 1 d . . . . .
H8 H 0.046207 0.458557 0.383757 0.067 Uiso 1 1 calc R U . . .
C10 C 0.03013(18) 0.64355(13) 0.1603(2) 0.0628(5) Uani 1 1 d . . . . .
H10 H -0.009675 0.699622 0.141238 0.075 Uiso 1 1 calc R U . . .
C3 C 0.56430(16) 0.37182(13) 0.4885(3) 0.0624(5) Uani 1 1 d . . . . .
H3A H 0.600365 0.431192 0.523671 0.075 Uiso 1 1 calc R U . . .
H3B H 0.618938 0.339399 0.438672 0.075 Uiso 1 1 calc R U . . .
C9 C 0.00649(18) 0.58411(14) 0.2726(2) 0.0655(5) Uani 1 1 d . . . . .
H9 H -0.049396 0.601003 0.329001 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1481(2) 0.67195(14) -0.0488(3) 0.0723(6) Uani 1 1 d . . . . .
H12 H 0.114529 0.729601 -0.077181 0.087 Uiso 1 1 calc R U . . .
C2 C 0.55422(18) 0.32006(15) 0.6434(3) 0.0703(6) Uani 1 1 d . . . . .
H2A H 0.544270 0.256095 0.615813 0.084 Uiso 1 1 calc R U . . .
H2B H 0.632043 0.327544 0.737990 0.084 Uiso 1 1 calc R U . . .
C1 C 0.44618(19) 0.35085(15) 0.6990(3) 0.0707(6) Uani 1 1 d . . . . .
H1A H 0.462666 0.412009 0.743368 0.085 Uiso 1 1 calc R U . . .
H1B H 0.440885 0.312136 0.791120 0.085 Uiso 1 1 calc R U . . .
C14 C 0.2839(2) 0.55210(16) -0.0877(3) 0.0736(6) Uani 1 1 d . . . . .
H14 H 0.338827 0.530827 -0.142255 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2290(2) 0.63837(17) -0.1252(3) 0.0815(7) Uani 1 1 d . . . . .
H13 H 0.248827 0.673940 -0.205586 0.098 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
O2 C4 1.351(2) . ?
O2 C17 1.480(2) . ?
O1 C00A 1.224(2) . ?
C16 C7 1.404(2) . ?
C16 C11 1.406(2) . ?
C16 C15 1.401(2) . ?
C5 C6 1.504(2) . ?
C5 C4 1.336(2) . ?
C5 C00A 1.446(2) . ?
C7 C6 1.521(2) . ?
C7 C8 1.355(2) . ?
C6 H6 0.9800 . ?
C6 C17 1.555(2) . ?
C11 C10 1.405(3) . ?
C11 C12 1.413(3) . ?
C15 C17 1.503(3) . ?
C15 C14 1.367(3) . ?
C4 C3 1.482(2) . ?
C00A C1 1.512(3) . ?
C17 H17 0.9800 . ?
C8 H8 0.9300 . ?
C8 C9 1.417(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.365(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.527(3) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.358(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.501(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C13 1.405(3) . ?
C13 H13 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
C4 O2 C17 107.39(12) . . ?
C7 C16 C11 123.41(16) . . ?
C15 C16 C7 113.40(15) . . ?
C15 C16 C11 123.17(16) . . ?
C4 C5 C6 109.98(15) . . ?
C4 C5 C00A 121.77(16) . . ?
C00A C5 C6 128.24(14) . . ?
C16 C7 C6 108.11(14) . . ?
C8 C7 C16 118.87(15) . . ?
C8 C7 C6 133.02(15) . . ?
C5 C6 C7 114.65(13) . . ?
C5 C6 H6 111.9 . . ?
C5 C6 C17 101.34(13) . . ?
C7 C6 H6 111.9 . . ?
C7 C6 C17 104.50(13) . . ?
C17 C6 H6 111.9 . . ?
C16 C11 C12 115.75(18) . . ?
C10 C11 C16 116.27(16) . . ?
C10 C11 C12 127.96(18) . . ?
C16 C15 C17 108.19(14) . . ?
C14 C15 C16 119.31(18) . . ?
C14 C15 C17 132.47(18) . . ?
O2 C4 C3 118.50(15) . . ?
C5 C4 O2 114.98(15) . . ?
C5 C4 C3 126.52(17) . . ?
O1 C00A C5 123.02(17) . . ?
O1 C00A C1 121.93(17) . . ?
C5 C00A C1 115.02(15) . . ?
O2 C17 C6 106.28(13) . . ?
O2 C17 C15 111.05(14) . . ?
O2 C17 H17 111.2 . . ?
C6 C17 H17 111.2 . . ?
C15 C17 C6 105.81(13) . . ?
C15 C17 H17 111.2 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.79(17) . . ?
C9 C8 H8 120.6 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.19(16) . . ?
C9 C10 H10 119.9 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C4 C3 C2 109.18(15) . . ?
H3A C3 H3B 108.3 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.46(18) . . ?
C10 C9 H9 118.8 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.72(19) . . ?
C13 C12 H12 119.6 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 C3 113.16(16) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C00A C1 H1A 108.9 . . ?
C00A C1 H1B 108.9 . . ?
C2 C1 C00A 113.19(17) . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
C15 C14 H14 120.8 . . ?
C15 C14 C13 118.3(2) . . ?
C13 C14 H14 120.8 . . ?
C12 C13 C14 122.73(19) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?

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
O2 C4 C3 C2 -161.89(16) . . . . ?
O1 C00A C1 C2 147.60(19) . . . . ?
C16 C7 C6 C5 110.12(15) . . . . ?
C16 C7 C6 C17 0.11(17) . . . . ?
C16 C7 C8 C9 0.6(2) . . . . ?
C16 C11 C10 C9 0.1(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C16 C15 C17 O2 -114.71(15) . . . . ?
C16 C15 C17 C6 0.19(18) . . . . ?
C16 C15 C14 C13 0.6(3) . . . . ?
C5 C6 C17 O2 -1.47(16) . . . . ?
C5 C6 C17 C15 -119.60(14) . . . . ?
C5 C4 C3 C2 17.6(2) . . . . ?
C5 C00A C1 C2 -34.2(2) . . . . ?
C7 C16 C11 C10 0.3(2) . . . . ?
C7 C16 C11 C12 -178.31(15) . . . . ?
C7 C16 C15 C17 -0.13(19) . . . . ?
C7 C16 C15 C14 177.97(16) . . . . ?
C7 C6 C17 O2 117.95(13) . . . . ?
C7 C6 C17 C15 -0.18(17) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C6 C5 C4 O2 -0.9(2) . . . . ?
C6 C5 C4 C3 179.64(15) . . . . ?
C6 C5 C00A O1 6.8(3) . . . . ?
C6 C5 C00A C1 -171.34(16) . . . . ?
C6 C7 C8 C9 -178.43(16) . . . . ?
C11 C16 C7 C6 178.53(14) . . . . ?
C11 C16 C7 C8 -0.7(2) . . . . ?
C11 C16 C15 C17 -178.65(15) . . . . ?
C11 C16 C15 C14 -0.6(3) . . . . ?
C11 C10 C9 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C15 C16 C7 C6 0.01(18) . . . . ?
C15 C16 C7 C8 -179.25(14) . . . . ?
C15 C16 C11 C10 178.72(15) . . . . ?
C15 C16 C11 C12 0.1(2) . . . . ?
C15 C14 C13 C12 -0.1(3) . . . . ?
C4 O2 C17 C6 1.06(17) . . . . ?
C4 O2 C17 C15 115.67(15) . . . . ?
C4 C5 C6 C7 -110.46(16) . . . . ?
C4 C5 C6 C17 1.44(17) . . . . ?
C4 C5 C00A O1 -174.68(17) . . . . ?
C4 C5 C00A C1 7.2(2) . . . . ?
C4 C3 C2 C1 -43.8(2) . . . . ?
C00A C5 C6 C7 68.2(2) . . . . ?
C00A C5 C6 C17 -179.88(16) . . . . ?
C00A C5 C4 O2 -179.68(14) . . . . ?
C00A C5 C4 C3 0.9(3) . . . . ?
C17 O2 C4 C5 -0.13(19) . . . . ?
C17 O2 C4 C3 179.37(14) . . . . ?
C17 C15 C14 C13 178.12(19) . . . . ?
C8 C7 C6 C5 -70.8(2) . . . . ?
C8 C7 C6 C17 179.23(17) . . . . ?
C10 C11 C12 C13 -178.07(18) . . . . ?
C3 C2 C1 C00A 53.9(2) . . . . ?
C12 C11 C10 C9 178.61(17) . . . . ?
C14 C15 C17 O2 67.5(3) . . . . ?
C14 C15 C17 C6 -177.56(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
