# 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_KB690_0m
_database_code_depnum_ccdc_archive 'CCDC 2296090'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.37

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.546(4)
_cell_length_b                   6.518(3)
_cell_length_c                   15.600(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.428(9)
_cell_angle_gamma                90
_cell_volume                     837.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7078
_cell_measurement_theta_min      2.479
_cell_measurement_theta_max      30.191

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17575
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         30.515
_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 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5101
_reflns_number_gt                3824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.998

_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, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0393P)²+0.0904P] 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_abs_structure_details 
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5101
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.5452(3) 0.7753(3) 0.30352(13) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.3730(3) 0.8516(3) 0.28926(15) 0.0315(5) Uani 1 1 d . . . . .
H2A H 0.372802 1.003439 0.287647 0.038 Uiso 1 1 calc R U . . .
H2B H 0.331894 0.808296 0.340085 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2589(3) 0.7700(3) 0.20272(16) 0.0326(5) Uani 1 1 d . . . . .
H3A H 0.146362 0.813129 0.199361 0.039 Uiso 1 1 calc R U . . .
H3B H 0.289742 0.830738 0.151383 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2651(2) 0.5352(3) 0.19677(14) 0.0274(5) Uani 1 1 d . . . . .
H4A H 0.217414 0.473180 0.241974 0.033 Uiso 1 1 calc R U . . .
H4B H 0.200628 0.489561 0.137344 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4372(3) 0.4657(3) 0.21202(13) 0.0232(4) Uani 1 1 d . . . . .
C6 C 0.5664(2) 0.5442(3) 0.29252(13) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.7260(2) 0.4876(3) 0.27032(14) 0.0250(4) Uani 1 1 d . . . . .
H7A H 0.767015 0.604722 0.242172 0.030 Uiso 1 1 calc R U . . .
H7B H 0.810012 0.447451 0.324737 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6827(2) 0.3069(3) 0.20582(13) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.699947 0.175412 0.240058 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5017(2) 0.3374(3) 0.16298(12) 0.0235(4) Uani 1 1 d . . . . .
C10 C 0.5453(2) 0.4331(3) 0.37819(13) 0.0238(4) Uani 1 1 d . . . . .
H10A H 0.442710 0.480751 0.389657 0.029 Uiso 1 1 calc R U . . .
H10B H 0.534546 0.283929 0.366139 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6818(2) 0.4668(3) 0.46148(13) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.6975(2) 0.6489(3) 0.50961(13) 0.0239(4) Uani 1 1 d . . . . .
H12 H 0.618867 0.754207 0.491193 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8268(3) 0.6786(4) 0.58423(14) 0.0305(5) Uani 1 1 d . . . . .
H13 H 0.835753 0.803771 0.616400 0.037 Uiso 1 1 calc R U . . .
C14 C 0.9425(3) 0.5274(4) 0.61196(15) 0.0333(5) Uani 1 1 d . . . . .
H14 H 1.031432 0.549000 0.662602 0.040 Uiso 1 1 calc R U . . .
C15 C 0.9280(3) 0.3438(4) 0.56546(15) 0.0342(5) Uani 1 1 d . . . . .
H15 H 1.006617 0.238820 0.584591 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7979(3) 0.3134(4) 0.49060(13) 0.0283(5) Uani 1 1 d . . . . .
H16 H 0.788305 0.187147 0.459157 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8058(3) 0.1092(3) 0.11250(16) 0.0347(6) Uani 1 1 d . . . . .
H17A H 0.700941 0.055103 0.076040 0.042 Uiso 1 1 calc R U . . .
H17B H 0.848120 0.013663 0.162671 0.042 Uiso 1 1 calc R U . . .
C18 C 0.9239(3) 0.1259(4) 0.05724(16) 0.0378(6) Uani 1 1 d . . . . .
H18A H 0.939528 -0.009487 0.033488 0.057 Uiso 1 1 calc R U . . .
H18B H 1.027960 0.176974 0.094064 0.057 Uiso 1 1 calc R U . . .
H18C H 0.881442 0.221228 0.007943 0.057 Uiso 1 1 calc R U . . .
C19 C 0.4154(3) 0.2307(3) 0.08440(14) 0.0259(5) Uani 1 1 d . . . . .
C20 C 0.3498(3) 0.1367(4) 0.01899(15) 0.0318(5) Uani 1 1 d . . . . .
H20 H 0.297561 0.061883 -0.033032 0.038 Uiso 1 1 calc R U . . .
O1 O 0.66159(18) 0.8902(2) 0.32316(10) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.78289(17) 0.3099(2) 0.14588(9) 0.0267(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 O1 1.217(2) . ?
C1 C2 1.513(3) . ?
C1 C6 1.532(3) . ?
C2 C3 1.535(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.496(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.346(3) . ?
C5 C6 1.523(3) . ?
C6 C7 1.539(3) . ?
C6 C10 1.572(3) . ?
C7 C8 1.529(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.426(2) . ?
C8 C9 1.526(3) . ?
C8 H8 1.0000 . ?
C9 C19 1.431(3) . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.392(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O2 1.440(3) . ?
C17 C18 1.495(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.195(3) . ?
C20 H20 0.9500 . ?

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
O1 C1 C2 122.19(19) . . ?
O1 C1 C6 121.3(2) . . ?
C2 C1 C6 116.49(17) . . ?
C1 C2 C3 112.40(18) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 111.99(19) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 109.93(18) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C9 C5 C4 129.15(19) . . ?
C9 C5 C6 111.14(18) . . ?
C4 C5 C6 119.70(17) . . ?
C5 C6 C1 109.96(17) . . ?
C5 C6 C7 103.02(15) . . ?
C1 C6 C7 113.54(16) . . ?
C5 C6 C10 108.90(16) . . ?
C1 C6 C10 108.29(16) . . ?
C7 C6 C10 112.96(17) . . ?
C8 C7 C6 105.01(16) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
O2 C8 C9 115.25(16) . . ?
O2 C8 C7 109.81(16) . . ?
C9 C8 C7 103.15(16) . . ?
O2 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
C5 C9 C19 126.4(2) . . ?
C5 C9 C8 110.64(18) . . ?
C19 C9 C8 122.89(18) . . ?
C11 C10 C6 115.24(16) . . ?
C11 C10 H10A 108.5 . . ?
C6 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C6 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C16 118.47(19) . . ?
C12 C11 C10 121.91(18) . . ?
C16 C11 C10 119.61(18) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O2 C17 C18 108.65(18) . . ?
O2 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O2 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C9 177.0(2) . . ?
C19 C20 H20 180.0 . . ?
C8 O2 C17 112.84(16) . . ?

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
O1 C1 C2 C3 131.4(2) . . . . ?
C6 C1 C2 C3 -49.0(2) . . . . ?
C1 C2 C3 C4 53.5(2) . . . . ?
C2 C3 C4 C5 -52.5(2) . . . . ?
C3 C4 C5 C9 -129.6(2) . . . . ?
C3 C4 C5 C6 50.0(3) . . . . ?
C9 C5 C6 C1 135.90(18) . . . . ?
C4 C5 C6 C1 -43.8(2) . . . . ?
C9 C5 C6 C7 14.6(2) . . . . ?
C4 C5 C6 C7 -165.10(17) . . . . ?
C9 C5 C6 C10 -105.59(19) . . . . ?
C4 C5 C6 C10 74.7(2) . . . . ?
O1 C1 C6 C5 -138.50(19) . . . . ?
C2 C1 C6 C5 41.9(2) . . . . ?
O1 C1 C6 C7 -23.7(3) . . . . ?
C2 C1 C6 C7 156.69(17) . . . . ?
O1 C1 C6 C10 102.6(2) . . . . ?
C2 C1 C6 C10 -77.0(2) . . . . ?
C5 C6 C7 C8 -24.7(2) . . . . ?
C1 C6 C7 C8 -143.54(17) . . . . ?
C10 C6 C7 C8 92.66(19) . . . . ?
C6 C7 C8 O2 149.04(16) . . . . ?
C6 C7 C8 C9 25.68(19) . . . . ?
C4 C5 C9 C19 -2.3(3) . . . . ?
C6 C5 C9 C19 178.09(19) . . . . ?
C4 C5 C9 C8 -178.52(19) . . . . ?
C6 C5 C9 C8 1.9(2) . . . . ?
O2 C8 C9 C5 -137.29(18) . . . . ?
C7 C8 C9 C5 -17.6(2) . . . . ?
O2 C8 C9 C19 46.3(3) . . . . ?
C7 C8 C9 C19 166.01(18) . . . . ?
C5 C6 C10 C11 169.86(17) . . . . ?
C1 C6 C10 C11 -70.6(2) . . . . ?
C7 C6 C10 C11 56.0(2) . . . . ?
C6 C10 C11 C12 76.7(2) . . . . ?
C6 C10 C11 C16 -102.0(2) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C10 C11 C12 C13 -177.92(18) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C10 C11 C16 C15 177.78(18) . . . . ?
C9 C8 O2 C17 -91.0(2) . . . . ?
C7 C8 O2 C17 153.11(18) . . . . ?
C18 C17 O2 C8 -174.91(18) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane (3:2)'
