# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2287262'
loop_
_audit_author_name
_audit_author_address
'Onur Sahin'
;Sinop University
Turkey
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 O'
_chemical_formula_sum            'C26 H16 O'
_chemical_formula_weight         344.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   5.8787(3)
_cell_length_b                   25.8705(14)
_cell_length_c                   12.0671(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.194(2)
_cell_angle_gamma                90
_cell_volume                     1800.31(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9394
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-3 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number            41927
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4132
_reflns_number_gt                2508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;


_computing_data_collection       'APEX3 (Bruker, 2013)'
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae, 2020)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.5611P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4132
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3471(3) 0.46581(7) 0.24971(16) 0.0483(5) Uani 1 1 d . . . . .
H1 H 0.2228 0.4796 0.2772 0.058 Uiso 1 1 calc R U . . .
C2 C 0.3502(4) 0.46424(8) 0.13594(17) 0.0554(5) Uani 1 1 d . . . . .
H2 H 0.2244 0.4774 0.0849 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5361(4) 0.44355(8) 0.09539(16) 0.0560(6) Uani 1 1 d . . . . .
H3 H 0.5311 0.4427 0.0179 0.067 Uiso 1 1 calc R U . . .
C4 C 0.7277(3) 0.42433(8) 0.16778(16) 0.0521(5) Uani 1 1 d . . . . .
H4 H 0.8524 0.4109 0.1401 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7301(3) 0.42557(7) 0.28341(15) 0.0410(4) Uani 1 1 d . . . . .
C6 C 0.8876(3) 0.40997(7) 0.38335(15) 0.0447(5) Uani 1 1 d . . . . .
H6 H 1.0335 0.3955 0.3867 0.054 Uiso 1 1 calc R U . . .
C7 C 0.7867(3) 0.42001(7) 0.47122(15) 0.0410(4) Uani 1 1 d . . . . .
C8 C 0.5393(3) 0.44573(7) 0.32052(14) 0.0378(4) Uani 1 1 d . . . . .
C9 C 0.8676(3) 0.41417(7) 0.59356(15) 0.0426(4) Uani 1 1 d . . . . .
C10 C 1.0682(3) 0.43984(8) 0.64058(17) 0.0558(5) Uani 1 1 d . . . . .
H10 H 1.1487 0.4579 0.5938 0.067 Uiso 1 1 calc R U . . .
C11 C 1.1538(4) 0.43936(8) 0.75735(19) 0.0650(6) Uani 1 1 d . . . . .
H11 H 1.2919 0.4562 0.7873 0.078 Uiso 1 1 calc R U . . .
C12 C 1.0347(4) 0.41440(8) 0.82591(18) 0.0624(6) Uani 1 1 d . . . . .
H12 H 1.0886 0.4156 0.9036 0.075 Uiso 1 1 calc R U . . .
C13 C 0.8297(3) 0.38640(7) 0.78267(16) 0.0501(5) Uani 1 1 d . . . . .
C14 C 0.7107(4) 0.35956(9) 0.85590(17) 0.0631(6) Uani 1 1 d . . . . .
H14 H 0.7649 0.3615 0.9335 0.076 Uiso 1 1 calc R U . . .
C15 C 0.5193(4) 0.33115(9) 0.81561(18) 0.0681(6) Uani 1 1 d . . . . .
H15 H 0.4404 0.3146 0.8652 0.082 Uiso 1 1 calc R U . . .
C16 C 0.4409(4) 0.32675(8) 0.69908(17) 0.0582(5) Uani 1 1 d . . . . .
H16 H 0.3112 0.3065 0.6720 0.070 Uiso 1 1 calc R U . . .
C17 C 0.5505(3) 0.35160(7) 0.62321(15) 0.0431(4) Uani 1 1 d . . . . .
C18 C 0.7465(3) 0.38458(7) 0.66341(14) 0.0411(4) Uani 1 1 d . . . . .
C19 C 0.4655(3) 0.33912(7) 0.50499(16) 0.0442(4) Uani 1 1 d . . . . .
C20 C 0.3776(3) 0.32444(7) 0.41455(17) 0.0489(5) Uani 1 1 d . . . . .
C21 C 0.2514(3) 0.30816(7) 0.30538(15) 0.0433(4) Uani 1 1 d . . . . .
C22 C 0.0436(4) 0.28194(9) 0.29739(18) 0.0658(6) Uani 1 1 d . . . . .
H22 H -0.0100 0.2741 0.3630 0.079 Uiso 1 1 calc R U . . .
C23 C -0.0845(4) 0.26738(10) 0.1955(2) 0.0772(7) Uani 1 1 d . . . . .
H23 H -0.2227 0.2495 0.1927 0.093 Uiso 1 1 calc R U . . .
C24 C -0.0126(5) 0.27869(10) 0.0994(2) 0.0745(7) Uani 1 1 d . . . . .
H24 H -0.1013 0.2688 0.0303 0.089 Uiso 1 1 calc R U . . .
C25 C 0.1894(5) 0.30459(10) 0.10305(18) 0.0785(7) Uani 1 1 d . . . . .
H25 H 0.2381 0.3126 0.0362 0.094 Uiso 1 1 calc R U . . .
C26 C 0.3243(4) 0.31933(9) 0.20619(18) 0.0634(6) Uani 1 1 d . . . . .
H26 H 0.4635 0.3367 0.2081 0.076 Uiso 1 1 calc R U . . .
O1 O 0.57117(19) 0.44309(4) 0.43656(10) 0.0425(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 1.377(3) . ?
C1 C8 1.379(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.388(2) . ?
C5 C6 1.429(2) . ?
C6 C7 1.337(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.390(2) . ?
C7 C9 1.468(2) . ?
C8 O1 1.378(2) . ?
C9 C10 1.376(3) . ?
C9 C18 1.427(3) . ?
C10 C11 1.401(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.348(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.416(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.412(3) . ?
C13 C18 1.428(2) . ?
C14 C15 1.353(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.440(2) . ?
C17 C19 1.453(2) . ?
C19 C20 1.176(2) . ?
C20 C21 1.444(3) . ?
C21 C26 1.378(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.364(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.341(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(3) . ?
C25 H25 0.9300 . ?
C26 H26 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 C1 C8 116.05(18) . . ?
C2 C1 H1 122.0 . . ?
C8 C1 H1 122.0 . . ?
C1 C2 C3 121.74(18) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 121.23(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.34(19) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C8 C5 C4 118.71(16) . . ?
C8 C5 C6 105.41(15) . . ?
C4 C5 C6 135.88(18) . . ?
C7 C6 C5 107.47(16) . . ?
C7 C6 H6 126.3 . . ?
C5 C6 H6 126.3 . . ?
C6 C7 O1 111.32(15) . . ?
C6 C7 C9 132.10(16) . . ?
O1 C7 C9 116.45(15) . . ?
O1 C8 C1 125.59(16) . . ?
O1 C8 C5 110.50(14) . . ?
C1 C8 C5 123.91(17) . . ?
C10 C9 C18 120.08(17) . . ?
C10 C9 C7 116.71(17) . . ?
C18 C9 C7 123.20(15) . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.68(19) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.72(18) . . ?
C14 C13 C18 120.00(18) . . ?
C12 C13 C18 119.26(19) . . ?
C15 C14 C13 121.40(19) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 119.98(17) . . ?
C16 C17 C19 115.65(17) . . ?
C18 C17 C19 124.23(17) . . ?
C9 C18 C13 117.70(17) . . ?
C9 C18 C17 125.25(16) . . ?
C13 C18 C17 117.02(17) . . ?
C20 C19 C17 171.1(2) . . ?
C19 C20 C21 175.1(2) . . ?
C26 C21 C22 117.46(18) . . ?
C26 C21 C20 122.71(18) . . ?
C22 C21 C20 119.78(18) . . ?
C23 C22 C21 121.6(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.0(2) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C8 O1 C7 105.28(13) . . ?

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
C8 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C8 0.4(3) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C8 C5 C6 C7 1.2(2) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C5 C6 C7 O1 -1.8(2) . . . . ?
C5 C6 C7 C9 -177.31(18) . . . . ?
C2 C1 C8 O1 -179.48(16) . . . . ?
C2 C1 C8 C5 1.1(3) . . . . ?
C4 C5 C8 O1 179.13(15) . . . . ?
C6 C5 C8 O1 -0.25(19) . . . . ?
C4 C5 C8 C1 -1.4(3) . . . . ?
C6 C5 C8 C1 179.24(17) . . . . ?
C6 C7 C9 C10 57.4(3) . . . . ?
O1 C7 C9 C10 -117.93(18) . . . . ?
C6 C7 C9 C18 -123.9(2) . . . . ?
O1 C7 C9 C18 60.8(2) . . . . ?
C18 C9 C10 C11 -2.4(3) . . . . ?
C7 C9 C10 C11 176.32(18) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C10 C11 C12 C13 3.0(3) . . . . ?
C11 C12 C13 C14 178.6(2) . . . . ?
C11 C12 C13 C18 -0.1(3) . . . . ?
C12 C13 C14 C15 -177.6(2) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 2.0(3) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C18 -2.2(3) . . . . ?
C15 C16 C17 C19 173.59(18) . . . . ?
C10 C9 C18 C13 5.2(3) . . . . ?
C7 C9 C18 C13 -173.49(16) . . . . ?
C10 C9 C18 C17 -172.78(17) . . . . ?
C7 C9 C18 C17 8.5(3) . . . . ?
C14 C13 C18 C9 177.38(17) . . . . ?
C12 C13 C18 C9 -3.9(3) . . . . ?
C14 C13 C18 C17 -4.5(3) . . . . ?
C12 C13 C18 C17 174.19(16) . . . . ?
C16 C17 C18 C9 -176.96(18) . . . . ?
C19 C17 C18 C9 7.6(3) . . . . ?
C16 C17 C18 C13 5.1(3) . . . . ?
C19 C17 C18 C13 -170.38(16) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C20 C21 C22 C23 177.9(2) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C20 C21 C26 C25 -177.1(2) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
C1 C8 O1 C7 179.73(17) . . . . ?
C5 C8 O1 C7 -0.79(18) . . . . ?
C6 C7 O1 C8 1.62(19) . . . . ?
C9 C7 O1 C8 177.90(14) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4



