# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# 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 
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data_20201112-libs-xxl-1-150k
_database_code_depnum_ccdc_archive 'CCDC 2113583'
_audit_update_record             
;
2021-10-02 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_audit_creation_date             2020-11-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 O'
_chemical_formula_sum            'C22 H18 O'
_chemical_formula_weight         298.36
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.9796(2)
_cell_length_b                   18.2987(4)
_cell_length_c                   22.0157(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3214.64(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_min      3.6970
_cell_measurement_theta_max      28.7070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_min  0.89428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.977
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2733
_reflns_number_total             3810
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.266
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.069
_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)+(0.0397P)²+1.6193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C22(H22), C9(H9), C13(H13), C5(H5), C18(H18), C1(H1),
 C15(H15), C19(H19), C3(H3), C21(H21), C4(H4), C2(H2), C20(H20)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.76839(15) 0.43422(7) 0.42703(6) 0.0312(3) Uani 1 1 d . . . . .
C12 C 0.47098(19) 0.44014(8) 0.43012(8) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.3199(2) 0.36468(9) 0.51097(7) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.4610(2) 0.48402(9) 0.37806(8) 0.0206(4) Uani 1 1 d . . . . .
H11 H 0.5591 0.4968 0.3579 0.025 Uiso 1 1 calc R . . . .
C17 C 0.2430(2) 0.63092(9) 0.30664(8) 0.0228(4) Uani 1 1 d . . . . .
C10 C 0.3089(2) 0.50890(9) 0.35587(7) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.2957(2) 0.55357(9) 0.29910(8) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.1715(2) 0.44689(9) 0.43963(8) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.0731 0.4353 0.4601 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3236(2) 0.41892(9) 0.46060(7) 0.0196(3) Uani 1 1 d . . . . .
C22 C 0.2953(2) 0.67100(10) 0.35714(8) 0.0277(4) Uani 1 1 d . . . . .
H22 H 0.3632 0.6490 0.3862 0.033 Uiso 1 1 calc R . . . .
C9 C 0.1645(2) 0.49160(9) 0.38903(8) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.0618 0.5106 0.3768 0.029 Uiso 1 1 calc R . . . .
C13 C 0.6391(2) 0.42245(9) 0.45407(8) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.6460 0.4010 0.4923 0.028 Uiso 1 1 calc R . . . .
C5 C 0.4032(2) 0.29782(9) 0.50636(8) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.4731 0.2890 0.4733 0.029 Uiso 1 1 calc R . . . .
C18 C 0.1419(2) 0.66580(9) 0.26389(8) 0.0268(4) Uani 1 1 d . . . . .
H18 H 0.1071 0.6403 0.2296 0.032 Uiso 1 1 calc R . . . .
C1 C 0.2172(2) 0.37659(10) 0.56150(8) 0.0257(4) Uani 1 1 d . . . . .
H1 H 0.1606 0.4208 0.5655 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3273(2) 0.52451(9) 0.24478(8) 0.0273(4) Uani 1 1 d . . . . .
H15 H 0.3215 0.5559 0.2116 0.033 Uiso 1 1 calc R . . . .
C19 C 0.0924(2) 0.73774(10) 0.27169(9) 0.0321(4) Uani 1 1 d . . . . .
H19 H 0.0241 0.7601 0.2429 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2817(2) 0.25710(10) 0.60013(9) 0.0320(4) Uani 1 1 d . . . . .
H3 H 0.2690 0.2213 0.6297 0.038 Uiso 1 1 calc R . . . .
C21 C 0.2472(3) 0.74313(10) 0.36456(9) 0.0332(4) Uani 1 1 d . . . . .
H21 H 0.2843 0.7693 0.3982 0.040 Uiso 1 1 calc R . . . .
C4 C 0.3833(2) 0.24449(9) 0.55026(9) 0.0301(4) Uani 1 1 d . . . . .
H4 H 0.4384 0.2000 0.5463 0.036 Uiso 1 1 calc R . . . .
C2 C 0.1989(2) 0.32330(10) 0.60577(8) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.1309 0.3320 0.6393 0.036 Uiso 1 1 calc R . . . .
C20 C 0.1445(3) 0.77640(10) 0.32234(9) 0.0350(5) Uani 1 1 d . . . . .
H20 H 0.1105 0.8246 0.3279 0.042 Uiso 1 1 calc R . . . .
C16 C 0.3710(3) 0.44655(10) 0.23165(9) 0.0347(5) Uani 1 1 d . . . . .
H16A H 0.3220 0.4323 0.1936 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.3284 0.4159 0.2635 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.4905 0.4415 0.2294 0.052 Uiso 1 1 calc GR . . . .


_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 C13 1.210(2) . ?
C12 C11 1.402(2) . ?
C12 C7 1.409(2) . ?
C12 C13 1.477(2) . ?
C6 C7 1.488(2) . ?
C6 C5 1.396(2) . ?
C6 C1 1.399(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.385(2) . ?
C17 C14 1.486(2) . ?
C17 C22 1.396(2) . ?
C17 C18 1.395(2) . ?
C10 C14 1.497(2) . ?
C10 C9 1.400(2) . ?
C14 C15 1.333(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.395(2) . ?
C8 C9 1.383(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.384(3) . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.382(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.497(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C3 C2 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(3) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C11 C12 C7 119.98(14) . . ?
C11 C12 C13 117.97(14) . . ?
C7 C12 C13 121.86(15) . . ?
C5 C6 C7 121.38(15) . . ?
C5 C6 C1 118.25(15) . . ?
C1 C6 C7 120.02(15) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 C12 121.78(15) . . ?
C10 C11 H11 119.1 . . ?
C22 C17 C14 120.33(15) . . ?
C18 C17 C14 121.62(16) . . ?
C18 C17 C22 118.04(16) . . ?
C11 C10 C14 122.37(15) . . ?
C11 C10 C9 117.55(15) . . ?
C9 C10 C14 120.07(14) . . ?
C17 C14 C10 116.53(15) . . ?
C15 C14 C17 122.27(16) . . ?
C15 C14 C10 121.20(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C7 121.23(15) . . ?
C12 C7 C6 123.72(15) . . ?
C8 C7 C12 117.85(15) . . ?
C8 C7 C6 118.29(15) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.82(17) . . ?
C21 C22 H22 119.6 . . ?
C10 C9 H9 119.3 . . ?
C8 C9 C10 121.37(15) . . ?
C8 C9 H9 119.3 . . ?
O1 C13 C12 124.02(16) . . ?
O1 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.85(17) . . ?
C4 C5 H5 119.6 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.09(17) . . ?
C19 C18 H18 119.5 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.76(17) . . ?
C2 C1 H1 119.6 . . ?
C14 C15 H15 116.6 . . ?
C14 C15 C16 126.70(16) . . ?
C16 C15 H15 116.6 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.98(17) . . ?
C20 C19 H19 120.0 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.74(17) . . ?
C2 C3 H3 120.1 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.37(18) . . ?
C20 C21 H21 119.8 . . ?
C5 C4 C3 120.28(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.11(17) . . ?
C3 C2 H2 119.9 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.69(17) . . ?
C21 C20 H20 120.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C12 C11 C10 C14 -177.78(15) . . . . ?
C12 C11 C10 C9 3.0(2) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C11 C12 C7 C6 171.52(15) . . . . ?
C11 C12 C7 C8 -4.2(2) . . . . ?
C11 C12 C13 O1 -11.2(2) . . . . ?
C11 C10 C14 C17 -111.96(18) . . . . ?
C11 C10 C14 C15 69.1(2) . . . . ?
C11 C10 C9 C8 -4.6(2) . . . . ?
C17 C14 C15 C16 -176.09(17) . . . . ?
C17 C22 C21 C20 0.9(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C10 C14 C15 C16 2.8(3) . . . . ?
C14 C17 C22 C21 179.87(16) . . . . ?
C14 C17 C18 C19 179.44(16) . . . . ?
C14 C10 C9 C8 176.17(16) . . . . ?
C7 C12 C11 C10 1.4(2) . . . . ?
C7 C12 C13 O1 173.64(16) . . . . ?
C7 C6 C5 C4 -172.46(15) . . . . ?
C7 C6 C1 C2 173.25(16) . . . . ?
C7 C8 C9 C10 1.8(3) . . . . ?
C22 C17 C14 C10 36.0(2) . . . . ?
C22 C17 C14 C15 -145.09(18) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C22 C21 C20 C19 -1.4(3) . . . . ?
C9 C10 C14 C17 67.2(2) . . . . ?
C9 C10 C14 C15 -111.68(19) . . . . ?
C9 C8 C7 C12 2.6(2) . . . . ?
C9 C8 C7 C6 -173.30(15) . . . . ?
C13 C12 C11 C10 -173.85(15) . . . . ?
C13 C12 C7 C6 -13.5(2) . . . . ?
C13 C12 C7 C8 170.85(15) . . . . ?
C5 C6 C7 C12 -47.5(2) . . . . ?
C5 C6 C7 C8 128.19(17) . . . . ?
C5 C6 C1 C2 0.0(2) . . . . ?
C18 C17 C14 C10 -144.43(16) . . . . ?
C18 C17 C14 C15 34.5(3) . . . . ?
C18 C17 C22 C21 0.3(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C1 C6 C7 C12 139.45(17) . . . . ?
C1 C6 C7 C8 -44.9(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
