# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_210611kk_auto
_database_code_depnum_ccdc_archive 'CCDC 2251568'
loop_
_audit_author_name
_audit_author_address
'Kazuma Kurokawa'
;Kyoto University
Japan
;
_audit_update_record             
;
2023-03-25 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C25 H16 O2'
_chemical_formula_sum            'C25 H16 O2'
_chemical_formula_weight         348.404
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.6918(3)
_cell_length_b                   5.05931(11)
_cell_length_c                   21.7368(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.000(2)
_cell_angle_gamma                90
_cell_volume                     1641.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.6910
_cell_measurement_theta_min      4.2480
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             730.252
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.9953
_diffrn_reflns_Laue_measured_fraction_max 0.9788
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11768
_diffrn_reflns_point_group_measured_fraction_full 0.9953
_diffrn_reflns_point_group_measured_fraction_max 0.9788
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.39
_diffrn_reflns_theta_min         4.28
_diffrn_ambient_temperature      93.0
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.9788
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00  30.00   92
  2  ω    -84.00 -38.00   0.50    0.50    --    5.00  60.00  60.00   92
  3  ω   -133.00 -37.00   0.50    0.50    --  -43.80  60.00 120.00  192
  4  ω   -133.00  46.00   0.50    0.50    --  -43.80  40.00  -6.65  358
  5  ω   -192.00 -13.00   0.50    0.85    -- -102.60  10.00  30.00  358
  6  ω   -192.00 -37.00   0.50    0.85    -- -102.60  60.00 174.46  310
  7  ω   -192.00 -37.00   0.50    0.85    -- -102.60  60.00 146.66  310
  8  ω   -192.00 -37.00   0.50    0.85    -- -102.60  60.00 126.21  310
  9  ω   -192.00 -13.00   0.50    0.85    -- -102.60  30.00 120.00  358
 10  ω   -192.00 -37.00   0.50    0.85    -- -102.60  60.00  28.58  310
 11  ω   -168.00 -43.00   0.50    0.85    -- -102.60  20.00  90.00  250
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2882
_reflns_number_total             3238
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.2967
_refine_diff_density_min         -0.2002
_refine_diff_density_rms         0.0550
_refine_ls_d_res_high            0.8045
_refine_ls_d_res_low             10.3365
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.0419
_refine_ls_shift/su_max          0.1661
_refine_ls_shift/su_mean         0.0047
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.6245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1081
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C19(H19), C8(H8), C6(H6), C14(H14), C5(H5), C18(H18),
 C22(H22), C20(H20), C23(H23), C13(H13)
2.b Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
2.c Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
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_refinement_flags_posn
O26 O 0.19749(6) 0.17564(18) 0.34477(4) 0.0244(2) Uani 1.000000 .
O25 O 0.21286(6) 1.05604(19) 0.73916(4) 0.0264(2) Uani 1.000000 .
H25 H 0.2123(9) 1.149(2) 0.7711(5) 0.0396(4) Uiso 1.000000 GR
C4 C 0.17179(8) 0.6666(2) 0.59964(6) 0.0189(3) Uani 1.000000 .
C1 C 0.35240(8) 1.1799(2) 0.63501(6) 0.0198(3) Uani 1.000000 .
C21 C 0.40780(8) 1.3876(3) 0.66685(6) 0.0214(3) Uani 1.000000 .
C9 C 0.14921(8) 0.4873(2) 0.54671(6) 0.0191(3) Uani 1.000000 .
C17 C 0.35736(8) 1.0677(2) 0.57649(6) 0.0197(3) Uani 1.000000 .
C15 C 0.26405(8) 0.6874(2) 0.50415(6) 0.0192(3) Uani 1.000000 .
C10 C 0.19502(8) 0.4988(2) 0.49791(6) 0.0194(3) Uani 1.000000 .
C11 C 0.17172(8) 0.3259(2) 0.44407(6) 0.0200(3) Uani 1.000000 .
H11 H 0.12469(8) 0.2017(2) 0.43916(6) 0.0240(3) Uiso 1.000000 R
C3 C 0.24326(8) 0.8543(2) 0.60551(6) 0.0190(3) Uani 1.000000 .
C2 C 0.28415(8) 1.0580(2) 0.65549(6) 0.0196(3) Uani 1.000000 .
C12 C 0.21638(8) 0.3359(2) 0.39890(6) 0.0205(3) Uani 1.000000 .
C7 C 0.03679(8) 0.2851(3) 0.58775(6) 0.0236(3) Uani 1.000000 .
H7 H -0.00797(8) 0.1545(3) 0.58418(6) 0.0283(3) Uiso 1.000000 R
C24 C 0.27381(8) 1.1563(3) 0.71242(6) 0.0211(3) Uani 1.000000 .
C19 C 0.47708(8) 1.3771(3) 0.58209(7) 0.0252(3) Uani 1.000000 .
H19 H 0.52015(8) 1.4448(3) 0.56364(7) 0.0302(4) Uiso 1.000000 R
C16 C 0.28754(8) 0.8619(2) 0.55878(6) 0.0187(3) Uani 1.000000 .
C8 C 0.08162(8) 0.2971(3) 0.54279(6) 0.0225(3) Uani 1.000000 .
H8 H 0.06691(8) 0.1743(3) 0.50804(6) 0.0270(3) Uiso 1.000000 R
C6 C 0.05713(8) 0.4656(3) 0.63879(6) 0.0238(3) Uani 1.000000 .
H6 H 0.02529(8) 0.4600(3) 0.66951(6) 0.0286(3) Uiso 1.000000 R
C14 C 0.30778(8) 0.6909(3) 0.45599(6) 0.0220(3) Uani 1.000000 .
H14 H 0.35408(8) 0.8163(3) 0.45940(6) 0.0264(3) Uiso 1.000000 R
C5 C 0.12318(8) 0.6514(3) 0.64472(6) 0.0227(3) Uani 1.000000 .
H5 H 0.13654(8) 0.7724(3) 0.67984(6) 0.0273(3) Uiso 1.000000 R
C18 C 0.42087(8) 1.1680(3) 0.55047(6) 0.0231(3) Uani 1.000000 .
H18 H 0.42659(8) 1.0965(3) 0.51152(6) 0.0277(3) Uiso 1.000000 R
C22 C 0.39360(9) 1.4831(3) 0.72429(6) 0.0238(3) Uani 1.000000 .
H22 H 0.42880(9) 1.6245(3) 0.74776(6) 0.0285(3) Uiso 1.000000 R
C20 C 0.47156(8) 1.4856(3) 0.63859(7) 0.0243(3) Uani 1.000000 .
H20 H 0.51039(8) 1.6261(3) 0.65867(7) 0.0292(3) Uiso 1.000000 R
C23 C 0.32881(9) 1.3697(3) 0.74547(6) 0.0237(3) Uani 1.000000 .
H23 H 0.31988(9) 1.4356(3) 0.78394(6) 0.0285(3) Uiso 1.000000 R
C13 C 0.28553(8) 0.5198(3) 0.40484(6) 0.0230(3) Uani 1.000000 .
H13 H 0.31653(8) 0.5252(3) 0.37361(6) 0.0276(3) Uiso 1.000000 R
C27 C 0.12525(9) -0.0093(3) 0.33427(6) 0.0255(3) Uani 1.000000 .
H27a H 0.1204(5) -0.1130(14) 0.2952(3) 0.0382(4) Uiso 1.000000 GR
H27b H 0.1368(3) -0.1280(13) 0.3716(2) 0.0382(4) Uiso 1.000000 GR
H27c H 0.06912(14) 0.0865(3) 0.3288(5) 0.0382(4) Uiso 1.000000 GR


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
O26 C12 1.3836(15) . ?
O26 C27 1.4328(15) . ?
O25 H25 0.8400 . ?
O25 C24 1.3616(15) . ?
C4 C9 1.4213(17) . ?
C4 C3 1.4451(17) . ?
C4 C5 1.4176(17) . ?
C1 C21 1.4024(18) . ?
C1 C17 1.4170(17) . ?
C1 C2 1.4214(17) . ?
C21 C22 1.4192(18) . ?
C21 C20 1.4158(18) . ?
C9 C10 1.4549(17) . ?
C9 C8 1.4150(18) . ?
C17 C16 1.4739(17) . ?
C17 C18 1.3854(17) . ?
C15 C10 1.4183(17) . ?
C15 C16 1.4334(17) . ?
C15 C14 1.4183(17) . ?
C10 C11 1.4156(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3721(17) . ?
C3 C2 1.4911(17) . ?
C3 C16 1.3972(16) . ?
C2 C24 1.3888(17) . ?
C12 C13 1.4046(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3706(18) . ?
C7 C6 1.3954(19) . ?
C24 C23 1.4293(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.4123(18) . ?
C19 C20 1.3723(19) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.3758(18) . ?
C14 H14 0.9500 . ?
C14 C13 1.3664(18) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.3652(19) . ?
C20 H20 0.9500 . ?
C23 H23 0.9500 . ?
C13 H13 0.9500 . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 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
C27 O26 C12 117.99(10) . . ?
C24 O25 H25 109.5 . . ?
C3 C4 C9 118.91(11) . . ?
C5 C4 C9 118.18(11) . . ?
C5 C4 C3 122.90(11) . . ?
C17 C1 C21 123.07(12) . . ?
C2 C1 C21 125.64(12) . . ?
C2 C1 C17 111.29(11) . . ?
C22 C21 C1 116.58(12) . . ?
C20 C21 C1 117.50(12) . . ?
C20 C21 C22 125.92(12) . . ?
C10 C9 C4 120.60(11) . . ?
C8 C9 C4 118.51(11) . . ?
C8 C9 C10 120.89(11) . . ?
C16 C17 C1 105.96(10) . . ?
C18 C17 C1 117.77(12) . . ?
C18 C17 C16 136.27(12) . . ?
C16 C15 C10 119.14(11) . . ?
C14 C15 C10 117.85(11) . . ?
C14 C15 C16 123.00(11) . . ?
C15 C10 C9 119.47(11) . . ?
C11 C10 C9 121.24(11) . . ?
C11 C10 C15 119.30(11) . . ?
H11 C11 C10 119.66(7) . . ?
C12 C11 C10 120.67(11) . . ?
C12 C11 H11 119.66(7) . . ?
C2 C3 C4 131.77(11) . . ?
C16 C3 C4 120.03(11) . . ?
C16 C3 C2 108.19(10) . . ?
C3 C2 C1 105.54(10) . . ?
C24 C2 C1 115.49(11) . . ?
C24 C2 C3 138.97(12) . . ?
C11 C12 O26 124.35(11) . . ?
C13 C12 O26 115.01(11) . . ?
C13 C12 C11 120.63(11) . . ?
C8 C7 H7 120.12(8) . . ?
C6 C7 H7 120.12(7) . . ?
C6 C7 C8 119.76(12) . . ?
C2 C24 O25 122.53(11) . . ?
C23 C24 O25 117.49(11) . . ?
C23 C24 C2 119.98(12) . . ?
C18 C19 H19 118.91(7) . . ?
C20 C19 H19 118.91(8) . . ?
C20 C19 C18 122.19(12) . . ?
C15 C16 C17 129.17(11) . . ?
C3 C16 C17 109.02(11) . . ?
C3 C16 C15 121.81(11) . . ?
C7 C8 C9 121.83(12) . . ?
H8 C8 C9 119.08(7) . . ?
H8 C8 C7 119.08(8) . . ?
H6 C6 C7 119.93(7) . . ?
C5 C6 C7 120.15(12) . . ?
C5 C6 H6 119.93(7) . . ?
H14 C14 C15 118.92(7) . . ?
C13 C14 C15 122.17(12) . . ?
C13 C14 H14 118.92(7) . . ?
C6 C5 C4 121.52(12) . . ?
H5 C5 C4 119.24(7) . . ?
H5 C5 C6 119.24(7) . . ?
C19 C18 C17 119.70(12) . . ?
H18 C18 C17 120.15(7) . . ?
H18 C18 C19 120.15(7) . . ?
H22 C22 C21 120.35(7) . . ?
C23 C22 C21 119.29(12) . . ?
C23 C22 H22 120.35(8) . . ?
C19 C20 C21 119.78(12) . . ?
H20 C20 C21 120.11(8) . . ?
H20 C20 C19 120.11(8) . . ?
C22 C23 C24 123.01(12) . . ?
H23 C23 C24 118.50(7) . . ?
H23 C23 C22 118.50(8) . . ?
C14 C13 C12 119.36(11) . . ?
H13 C13 C12 120.32(7) . . ?
H13 C13 C14 120.32(7) . . ?
H27a C27 O26 109.5 . . ?
H27b C27 O26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 O26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?

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
O26 C12 C11 C10 -179.56(12) . . . . ?
O26 C12 C13 C14 178.58(11) . . . . ?
O25 C24 C2 C1 -178.35(12) . . . . ?
O25 C24 C2 C3 2.52(17) . . . . ?
O25 C24 C23 C22 178.55(11) . . . . ?
C4 C9 C10 C15 1.30(13) . . . . ?
C4 C9 C10 C11 -178.41(11) . . . . ?
C4 C9 C8 C7 1.21(14) . . . . ?
C4 C3 C2 C1 179.50(14) . . . . ?
C4 C3 C2 C24 -1.32(18) . . . . ?
C4 C3 C16 C17 -179.52(11) . . . . ?
C4 C3 C16 C15 0.17(13) . . . . ?
C4 C5 C6 C7 0.33(15) . . . . ?
C1 C21 C22 C23 0.49(13) . . . . ?
C1 C21 C20 C19 0.04(13) . . . . ?
C1 C17 C16 C15 -179.66(9) . . . . ?
C1 C17 C16 C3 -0.01(11) . . . . ?
C1 C17 C18 C19 -0.65(13) . . . . ?
C1 C2 C3 C16 0.20(11) . . . . ?
C1 C2 C24 C23 1.18(13) . . . . ?
C21 C22 C23 C24 0.11(15) . . . . ?
C21 C20 C19 C18 -0.03(15) . . . . ?
C9 C10 C15 C16 0.37(13) . . . . ?
C9 C10 C15 C14 179.37(11) . . . . ?
C9 C10 C11 C12 -178.97(12) . . . . ?
C9 C8 C7 C6 0.52(15) . . . . ?
C17 C16 C15 C10 178.51(13) . . . . ?
C17 C16 C15 C14 -0.44(15) . . . . ?
C17 C16 C3 C2 -0.12(11) . . . . ?
C17 C18 C19 C20 0.34(15) . . . . ?
C15 C10 C11 C12 1.32(14) . . . . ?
C15 C16 C3 C2 179.56(12) . . . . ?
C15 C14 C13 C12 0.83(15) . . . . ?
C10 C11 C12 C13 -0.64(14) . . . . ?
C11 C12 C13 C14 -0.43(14) . . . . ?
C3 C2 C24 C23 -177.94(16) . . . . ?
C2 C24 C23 C22 -1.01(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
