# Electronic Supplementary Material (ESI) for ChemComm.
# 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).
# 
# 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_KA845_0m
_database_code_depnum_ccdc_archive 'CCDC 2052967'
loop_
_audit_author_name
_audit_author_address
'Dr. B.Sridhar'
;Department of Analytical and Structural Chemistry, CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-12-29 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40

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                   6.549(3)
_cell_length_b                   12.882(5)
_cell_length_c                   10.906(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.723(12)
_cell_angle_gamma                90
_cell_volume                     916.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9297
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      56.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33298
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5572
_reflns_number_gt                4019
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.999

_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 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.0917P] 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 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.1913(3) 0.48766(16) 0.5563(2) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.0966(4) 0.46208(19) 0.4286(2) 0.0398(5) Uani 1 1 d . . . . .
H2A H 0.018692 0.398038 0.428472 0.048 Uiso 1 1 calc R U . . .
H2B H 0.200474 0.456058 0.370510 0.048 Uiso 1 1 calc R U . . .
C3 C -0.0447(4) 0.5564(2) 0.3982(2) 0.0418(5) Uani 1 1 d . . . . .
H3 H 0.041851 0.611210 0.367861 0.050 Uiso 1 1 calc R U . . .
C4 C -0.1075(4) 0.5929(2) 0.5237(2) 0.0399(5) Uani 1 1 d . . . . .
H4A H -0.128804 0.667392 0.524792 0.048 Uiso 1 1 calc R U . . .
H4B H -0.231171 0.558217 0.545060 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0752(3) 0.56166(16) 0.6094(2) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.1266(3) 0.60042(17) 0.7288(2) 0.0348(5) Uani 1 1 d . . . . .
C7 C 0.3065(3) 0.56487(17) 0.7904(2) 0.0339(4) Uani 1 1 d . . . . .
C8 C 0.4326(3) 0.48887(17) 0.7393(2) 0.0334(5) Uani 1 1 d . . . . .
C9 C 0.3717(3) 0.44701(15) 0.6209(2) 0.0318(4) Uani 1 1 d . . . . .
C10 C 0.6192(4) 0.45405(18) 0.8035(2) 0.0403(5) Uani 1 1 d . . . . .
H10 H 0.660010 0.482022 0.880235 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7387(4) 0.38047(19) 0.7543(3) 0.0448(6) Uani 1 1 d . . . . .
C12 C 0.6760(4) 0.3365(2) 0.6391(3) 0.0458(6) Uani 1 1 d . . . . .
H12 H 0.756312 0.285482 0.606534 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4980(4) 0.36772(16) 0.5739(2) 0.0384(5) Uani 1 1 d . . . . .
C14 C -0.2143(5) 0.5366(2) 0.2975(2) 0.0525(7) Uani 1 1 d . . . . .
C15 C -0.4084(5) 0.5564(4) 0.3096(3) 0.0864(13) Uani 1 1 d . . . . .
H15A H -0.505893 0.544685 0.244118 0.104 Uiso 1 1 calc R U . . .
H15B H -0.448385 0.582103 0.383627 0.104 Uiso 1 1 calc R U . . .
C16 C -0.1436(8) 0.4951(4) 0.1797(3) 0.0908(13) Uani 1 1 d . . . . .
H16A H -0.257661 0.491916 0.118567 0.136 Uiso 1 1 calc R U . . .
H16B H -0.087786 0.426832 0.193442 0.136 Uiso 1 1 calc R U . . .
H16C H -0.040275 0.540118 0.151640 0.136 Uiso 1 1 calc R U . . .
C17 C -0.0094(4) 0.6793(2) 0.7846(3) 0.0503(6) Uani 1 1 d . . . . .
H17A H -0.028292 0.737978 0.730646 0.075 Uiso 1 1 calc R U . . .
H17B H 0.053733 0.701533 0.862764 0.075 Uiso 1 1 calc R U . . .
H17C H -0.139953 0.648392 0.795840 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3712(4) 0.6075(2) 0.9156(2) 0.0445(6) Uani 1 1 d . . . . .
C19 C 0.5661(7) 0.7396(4) 1.0220(4) 0.0881(13) Uani 1 1 d . . . . .
H19A H 0.640347 0.801173 1.003737 0.132 Uiso 1 1 calc R U . . .
H19B H 0.654788 0.693345 1.070531 0.132 Uiso 1 1 calc R U . . .
H19C H 0.451581 0.757990 1.067212 0.132 Uiso 1 1 calc R U . . .
C20 C 0.9355(5) 0.3423(3) 0.8231(3) 0.0647(9) Uani 1 1 d . . . . .
H20A H 1.047289 0.351111 0.772398 0.097 Uiso 1 1 calc R U . . .
H20B H 0.921841 0.270135 0.842871 0.097 Uiso 1 1 calc R U . . .
H20C H 0.961789 0.381513 0.897613 0.097 Uiso 1 1 calc R U . . .
C21 C 0.5573(5) 0.2604(2) 0.4019(3) 0.0595(8) Uani 1 1 d . . . . .
H21A H 0.493798 0.243707 0.321879 0.089 Uiso 1 1 calc R U . . .
H21B H 0.580942 0.197843 0.448696 0.089 Uiso 1 1 calc R U . . .
H21C H 0.685520 0.294758 0.393517 0.089 Uiso 1 1 calc R U . . .
O1 O 0.4928(4) 0.68871(16) 0.90831(18) 0.0594(6) Uani 1 1 d . . . . .
O2 O 0.3208(5) 0.5742(3) 1.0103(2) 0.1063(12) Uani 1 1 d . . . . .
O3 O 0.4260(3) 0.32733(15) 0.46380(18) 0.0519(5) 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 C5 1.376(3) . ?
C1 C9 1.425(3) . ?
C1 C2 1.513(3) . ?
C2 C3 1.547(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.518(3) . ?
C3 C4 1.535(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.410(3) . ?
C6 C7 1.385(3) . ?
C6 C17 1.511(3) . ?
C7 C8 1.424(3) . ?
C7 C18 1.500(3) . ?
C8 C9 1.425(3) . ?
C8 C10 1.430(3) . ?
C9 C13 1.435(3) . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.409(4) . ?
C11 C20 1.519(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 O3 1.357(3) . ?
C14 C15 1.314(5) . ?
C14 C16 1.499(5) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O2 1.190(4) . ?
C18 O1 1.321(3) . ?
C19 O1 1.449(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.426(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C5 C1 C9 120.70(19) . . ?
C5 C1 C2 109.84(19) . . ?
C9 C1 C2 129.5(2) . . ?
C1 C2 C3 102.64(19) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.2 . . ?
C14 C3 C4 117.6(2) . . ?
C14 C3 C2 114.4(2) . . ?
C4 C3 C2 104.42(19) . . ?
C14 C3 H3 106.6 . . ?
C4 C3 H3 106.6 . . ?
C2 C3 H3 106.6 . . ?
C5 C4 C3 102.32(19) . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C1 C5 C6 122.42(19) . . ?
C1 C5 C4 111.15(19) . . ?
C6 C5 C4 126.4(2) . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 C17 122.2(2) . . ?
C5 C6 C17 120.4(2) . . ?
C6 C7 C8 122.33(19) . . ?
C6 C7 C18 119.1(2) . . ?
C8 C7 C18 118.61(19) . . ?
C7 C8 C9 119.14(18) . . ?
C7 C8 C10 121.6(2) . . ?
C9 C8 C10 119.3(2) . . ?
C1 C9 C8 117.89(18) . . ?
C1 C9 C13 124.3(2) . . ?
C8 C9 C13 117.82(19) . . ?
C11 C10 C8 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C8 C10 H10 119.3 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 C20 121.4(3) . . ?
C12 C11 C20 118.9(3) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O3 C13 C12 124.3(2) . . ?
O3 C13 C9 114.9(2) . . ?
C12 C13 C9 120.8(2) . . ?
C15 C14 C16 121.6(3) . . ?
C15 C14 C3 123.4(3) . . ?
C16 C14 C3 114.9(3) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 O1 123.3(3) . . ?
O2 C18 C7 125.4(3) . . ?
O1 C18 C7 111.2(2) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 O1 C19 117.7(3) . . ?
C13 O3 C21 118.1(2) . . ?

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
C5 C1 C2 C3 18.7(2) . . . . ?
C9 C1 C2 C3 -161.2(2) . . . . ?
C1 C2 C3 C14 -159.4(2) . . . . ?
C1 C2 C3 C4 -29.5(2) . . . . ?
C14 C3 C4 C5 157.3(2) . . . . ?
C2 C3 C4 C5 29.4(2) . . . . ?
C9 C1 C5 C6 -0.3(3) . . . . ?
C2 C1 C5 C6 179.8(2) . . . . ?
C9 C1 C5 C4 179.9(2) . . . . ?
C2 C1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 C1 -18.9(3) . . . . ?
C3 C4 C5 C6 161.3(2) . . . . ?
C1 C5 C6 C7 3.1(3) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
C1 C5 C6 C17 -178.1(2) . . . . ?
C4 C5 C6 C17 1.6(4) . . . . ?
C5 C6 C7 C8 -2.7(3) . . . . ?
C17 C6 C7 C8 178.6(2) . . . . ?
C5 C6 C7 C18 177.5(2) . . . . ?
C17 C6 C7 C18 -1.3(4) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C18 C7 C8 C9 179.4(2) . . . . ?
C6 C7 C8 C10 179.2(2) . . . . ?
C18 C7 C8 C10 -1.0(3) . . . . ?
C5 C1 C9 C8 -2.9(3) . . . . ?
C2 C1 C9 C8 176.9(2) . . . . ?
C5 C1 C9 C13 178.1(2) . . . . ?
C2 C1 C9 C13 -2.1(4) . . . . ?
C7 C8 C9 C1 3.2(3) . . . . ?
C10 C8 C9 C1 -176.4(2) . . . . ?
C7 C8 C9 C13 -177.7(2) . . . . ?
C10 C8 C9 C13 2.7(3) . . . . ?
C7 C8 C10 C11 179.5(2) . . . . ?
C9 C8 C10 C11 -0.9(3) . . . . ?
C8 C10 C11 C12 -1.1(4) . . . . ?
C8 C10 C11 C20 -179.2(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C20 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 O3 -178.5(2) . . . . ?
C11 C12 C13 C9 0.7(4) . . . . ?
C1 C9 C13 O3 -4.3(3) . . . . ?
C8 C9 C13 O3 176.7(2) . . . . ?
C1 C9 C13 C12 176.4(2) . . . . ?
C8 C9 C13 C12 -2.6(3) . . . . ?
C4 C3 C14 C15 5.2(5) . . . . ?
C2 C3 C14 C15 128.2(4) . . . . ?
C4 C3 C14 C16 -176.5(3) . . . . ?
C2 C3 C14 C16 -53.5(4) . . . . ?
C6 C7 C18 O2 87.9(4) . . . . ?
C8 C7 C18 O2 -92.0(4) . . . . ?
C6 C7 C18 O1 -91.9(3) . . . . ?
C8 C7 C18 O1 88.3(3) . . . . ?
O2 C18 O1 C19 -0.6(5) . . . . ?
C7 C18 O1 C19 179.1(3) . . . . ?
C12 C13 O3 C21 -10.5(4) . . . . ?
C9 C13 O3 C21 170.3(2) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_KB56_0m
_database_code_depnum_ccdc_archive 'CCDC 2085118'
loop_
_audit_author_name
_audit_author_address
'Dr. B.Sridhar'
;Department of Analytical and Structural Chemistry, CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 O3'
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.35

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.4785(4)
_cell_length_b                   9.2084(4)
_cell_length_c                   10.5687(5)
_cell_angle_alpha                95.956(2)
_cell_angle_beta                 104.157(2)
_cell_angle_gamma                100.451(2)
_cell_volume                     777.25(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3438
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      20.92

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15804
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3555
_reflns_number_gt                2134
_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, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.1838P] 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         3555
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.3011(2) 0.58167(18) 0.66235(16) 0.0356(4) Uani 1 1 d . . . . .
C2 C 0.1843(2) 0.4479(2) 0.61680(18) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.072279 0.447173 0.607819 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2316(3) 0.3156(2) 0.58448(19) 0.0525(5) Uani 1 1 d . . . . .
H3 H 0.151521 0.227274 0.553621 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3964(3) 0.3146(2) 0.59795(18) 0.0493(5) Uani 1 1 d . . . . .
H4 H 0.428218 0.226173 0.575152 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5144(2) 0.4452(2) 0.64535(16) 0.0427(4) Uani 1 1 d . . . . .
H5 H 0.626151 0.443734 0.655433 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4700(2) 0.57976(18) 0.67860(15) 0.0353(4) Uani 1 1 d . . . . .
C7 C 0.5997(2) 0.7200(2) 0.72916(17) 0.0405(4) Uani 1 1 d . . . . .
C8 C 0.7750(2) 0.7135(2) 0.8016(2) 0.0551(5) Uani 1 1 d . . . . .
H8A H 0.847310 0.734104 0.744406 0.066 Uiso 1 1 calc R U . . .
H8B H 0.776171 0.613166 0.821678 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8436(2) 0.8247(2) 0.9300(2) 0.0546(5) Uani 1 1 d . . . . .
H9A H 0.962842 0.858089 0.944733 0.066 Uiso 1 1 calc R U . . .
H9B H 0.794171 0.911345 0.919996 0.066 Uiso 1 1 calc R U . . .
C10 C 0.8111(2) 0.7618(2) 1.0508(2) 0.0595(6) Uani 1 1 d . . . . .
H10A H 0.859100 0.839489 1.127068 0.071 Uiso 1 1 calc R U . . .
H10B H 0.869304 0.680990 1.064872 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6290(2) 0.7034(2) 1.04497(19) 0.0495(5) Uani 1 1 d . . . . .
H11A H 0.577112 0.633623 0.963763 0.059 Uiso 1 1 calc R U . . .
H11B H 0.624203 0.648547 1.117993 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5292(2) 0.8233(2) 1.05085(19) 0.0515(5) Uani 1 1 d . . . . .
H12A H 0.526479 0.872982 0.973995 0.062 Uiso 1 1 calc R U . . .
H12B H 0.585720 0.897348 1.128536 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3513(3) 0.7652(2) 1.05558(19) 0.0548(5) Uani 1 1 d . . . . .
H13A H 0.303816 0.849896 1.076475 0.066 Uiso 1 1 calc R U . . .
H13B H 0.353927 0.706334 1.126737 0.066 Uiso 1 1 calc R U . . .
C14 C 0.2369(2) 0.6694(2) 0.92761(18) 0.0474(5) Uani 1 1 d . . . . .
H14A H 0.283767 0.584619 0.905917 0.057 Uiso 1 1 calc R U . . .
H14B H 0.129131 0.631193 0.941633 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2137(2) 0.75425(19) 0.81448(18) 0.0414(4) Uani 1 1 d . . . . .
H15 H 0.173790 0.840937 0.826273 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2433(2) 0.72032(17) 0.69897(17) 0.0357(4) Uani 1 1 d . . . . .
C17 C 0.2168(2) 0.8264(2) 0.60261(18) 0.0421(4) Uani 1 1 d . . . . .
C18 C 0.2119(3) 0.8702(3) 0.3860(2) 0.0743(7) Uani 1 1 d . . . . .
H18A H 0.200517 0.815297 0.300808 0.111 Uiso 1 1 calc R U . . .
H18B H 0.308855 0.950087 0.408262 0.111 Uiso 1 1 calc R U . . .
H18C H 0.114972 0.910921 0.384009 0.111 Uiso 1 1 calc R U . . .
O1 O 0.56560(15) 0.84088(14) 0.71342(13) 0.0531(4) Uani 1 1 d . . . . .
O2 O 0.1842(2) 0.94596(15) 0.62565(13) 0.0686(4) Uani 1 1 d . . . . .
O3 O 0.22923(16) 0.77147(13) 0.48392(12) 0.0502(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 1.389(2) . ?
C1 C6 1.404(2) . ?
C1 C16 1.496(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(2) . ?
C7 O1 1.217(2) . ?
C7 C8 1.511(2) . ?
C8 C9 1.529(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.513(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.533(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.487(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.323(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(2) . ?
C17 O2 1.198(2) . ?
C17 O3 1.339(2) . ?
C18 O3 1.445(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 C1 C6 118.50(15) . . ?
C2 C1 C16 118.93(15) . . ?
C6 C1 C16 122.48(14) . . ?
C3 C2 C1 121.26(18) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.07(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.63(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.38(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.12(16) . . ?
C5 C6 C7 120.50(16) . . ?
C1 C6 C7 120.37(15) . . ?
O1 C7 C6 120.47(16) . . ?
O1 C7 C8 119.38(16) . . ?
C6 C7 C8 120.14(16) . . ?
C7 C8 C9 112.85(16) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.05(17) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 116.02(16) . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 114.46(16) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 114.07(16) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 114.73(16) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 112.62(15) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 127.36(16) . . ?
C16 C15 H15 116.3 . . ?
C14 C15 H15 116.3 . . ?
C15 C16 C17 117.52(16) . . ?
C15 C16 C1 122.94(15) . . ?
C17 C16 C1 119.53(15) . . ?
O2 C17 O3 122.99(16) . . ?
O2 C17 C16 124.87(18) . . ?
O3 C17 C16 112.12(15) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 O3 C18 115.62(15) . . ?

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
C6 C1 C2 C3 -1.7(3) . . . . ?
C16 C1 C2 C3 -178.47(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -179.70(16) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C16 C1 C6 C5 178.35(15) . . . . ?
C2 C1 C6 C7 -179.05(15) . . . . ?
C16 C1 C6 C7 -2.4(2) . . . . ?
C5 C6 C7 O1 153.09(17) . . . . ?
C1 C6 C7 O1 -26.2(2) . . . . ?
C5 C6 C7 C8 -27.4(2) . . . . ?
C1 C6 C7 C8 153.33(16) . . . . ?
O1 C7 C8 C9 47.1(2) . . . . ?
C6 C7 C8 C9 -132.40(18) . . . . ?
C7 C8 C9 C10 91.0(2) . . . . ?
C8 C9 C10 C11 -58.4(2) . . . . ?
C9 C10 C11 C12 -69.7(2) . . . . ?
C10 C11 C12 C13 -175.56(16) . . . . ?
C11 C12 C13 C14 -69.4(2) . . . . ?
C12 C13 C14 C15 -63.1(2) . . . . ?
C13 C14 C15 C16 124.0(2) . . . . ?
C14 C15 C16 C17 -177.57(16) . . . . ?
C14 C15 C16 C1 2.6(3) . . . . ?
C2 C1 C16 C15 81.6(2) . . . . ?
C6 C1 C16 C15 -95.1(2) . . . . ?
C2 C1 C16 C17 -98.27(19) . . . . ?
C6 C1 C16 C17 85.1(2) . . . . ?
C15 C16 C17 O2 6.6(3) . . . . ?
C1 C16 C17 O2 -173.56(17) . . . . ?
C15 C16 C17 O3 -171.76(15) . . . . ?
C1 C16 C17 O3 8.1(2) . . . . ?
O2 C17 O3 C18 4.1(3) . . . . ?
C16 C17 O3 C18 -177.53(15) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.037

