# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_S1
_database_code_depnum_ccdc_archive 'CCDC 2374532'
loop_
_audit_author_name
_audit_author_address
'Prema Vasudev'
;Central Institute of Medicinal and Aromatic Plants
India
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   15.9042(17)
_cell_length_b                   10.4909(11)
_cell_length_c                   10.2599(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.555(3)
_cell_angle_gamma                90
_cell_volume                     1677.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    42348
_cell_measurement_theta_min      7.093
_cell_measurement_theta_max      72.117

_exptl_crystal_description       prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.671
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42348
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         7.093
_diffrn_reflns_theta_max         72.117
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3133
_reflns_number_gt                3052
_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       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0896P)²+0.5251P] 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         3133
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.63962(9) 0.08712(12) 0.01826(13) 0.0584(4) Uani 1 1 d . . . . .
O2 O 0.69736(8) 0.00730(12) -0.15607(12) 0.0537(4) Uani 1 1 d . . . . .
C001 C 0.79696(9) -0.12965(14) -0.00992(14) 0.0373(4) Uani 1 1 d . . . . .
C002 C 0.77619(10) -0.05092(15) -0.12064(15) 0.0412(4) Uani 1 1 d . . . . .
C003 C 0.93649(10) -0.16275(15) -0.06178(16) 0.0431(4) Uani 1 1 d . . . . .
C004 C 0.73247(9) -0.14612(14) 0.07881(14) 0.0377(4) Uani 1 1 d . . . . .
H004 H 0.7417 -0.2277 0.1260 0.045 Uiso 1 1 calc R U . . .
C005 C 0.87775(10) -0.18646(15) 0.01836(15) 0.0410(4) Uani 1 1 d . . . . .
H005 H 0.8923 -0.2405 0.0913 0.049 Uiso 1 1 calc R U . . .
C006 C 0.74028(10) -0.03738(15) 0.17717(15) 0.0411(4) Uani 1 1 d . . . . .
C007 C 0.62313(10) -0.25697(18) -0.09775(16) 0.0481(4) Uani 1 1 d . . . . .
C008 C 0.91505(10) -0.08217(15) -0.17109(16) 0.0433(4) Uani 1 1 d . . . . .
O3 O 0.61923(10) -0.25198(15) -0.21648(13) 0.0677(4) Uani 1 1 d . . . . .
C009 C 0.83451(11) -0.02641(16) -0.20221(16) 0.0460(4) Uani 1 1 d . . . . .
H009 H 0.8197 0.0263 -0.2761 0.055 Uiso 1 1 calc R U . . .
C010 C 0.79287(11) -0.04329(18) 0.30258(16) 0.0492(4) Uani 1 1 d . . . . .
H010 H 0.8246 -0.1168 0.3285 0.059 Uiso 1 1 calc R U . . .
C011 C 0.64158(9) -0.14149(16) -0.00817(14) 0.0410(4) Uani 1 1 d . . . . .
H011 H 0.6007 -0.1425 0.0517 0.049 Uiso 1 1 calc R U . . .
C012 C 0.63288(10) -0.01278(17) -0.07885(16) 0.0460(4) Uani 1 1 d . . . . .
C013 C 0.69449(11) 0.07348(16) 0.14040(17) 0.0480(4) Uani 1 1 d . . . . .
C014 C 1.02683(11) -0.2115(2) -0.0482(2) 0.0575(5) Uani 1 1 d . . . . .
H01A H 1.0289 -0.3034 -0.0374 0.069 Uiso 1 1 calc R U . . .
H01B H 1.0646 -0.1726 0.0273 0.069 Uiso 1 1 calc R U . . .
C015 C 0.54857(12) 0.0108(2) -0.17214(19) 0.0617(5) Uani 1 1 d . . . . .
H01C H 0.5025 -0.0013 -0.1256 0.092 Uiso 1 1 calc R U . . .
H01D H 0.5472 0.0966 -0.2051 0.092 Uiso 1 1 calc R U . . .
H01E H 0.5422 -0.0478 -0.2453 0.092 Uiso 1 1 calc R U . . .
C016 C 0.99098(11) -0.06562(18) -0.23789(19) 0.0537(5) Uani 1 1 d . . . . .
H01F H 1.0176 0.0172 -0.2177 0.064 Uiso 1 1 calc R U . . .
H01G H 0.9739 -0.0748 -0.3336 0.064 Uiso 1 1 calc R U . . .
C017 C 0.61074(17) -0.3800(2) -0.0307(2) 0.0741(6) Uani 1 1 d . . . . .
H01H H 0.6160 -0.3658 0.0630 0.111 Uiso 1 1 calc R U . . .
H01I H 0.5547 -0.4133 -0.0670 0.111 Uiso 1 1 calc R U . . .
H01J H 0.6535 -0.4401 -0.0451 0.111 Uiso 1 1 calc R U . . .
C018 C 0.69977(14) 0.1759(2) 0.2271(2) 0.0642(5) Uani 1 1 d . . . . .
H018 H 0.6683 0.2496 0.2016 0.077 Uiso 1 1 calc R U . . .
C019 C 1.05160(13) -0.1725(2) -0.1784(2) 0.0693(6) Uani 1 1 d . . . . .
H01K H 1.1106 -0.1430 -0.1622 0.083 Uiso 1 1 calc R U . . .
H01L H 1.0461 -0.2444 -0.2390 0.083 Uiso 1 1 calc R U . . .
C020 C 0.75210(16) 0.1677(2) 0.3516(2) 0.0695(6) Uani 1 1 d . . . . .
H020 H 0.7558 0.2361 0.4101 0.083 Uiso 1 1 calc R U . . .
C021 C 0.79878(14) 0.0588(2) 0.38963(19) 0.0635(5) Uani 1 1 d . . . . .
H021 H 0.8342 0.0538 0.4734 0.076 Uiso 1 1 calc R U . . .


_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 C013 1.384(2) . ?
O1 C012 1.435(2) . ?
O2 C002 1.3765(19) . ?
O2 C012 1.4314(19) . ?
C001 C002 1.390(2) . ?
C001 C005 1.393(2) . ?
C001 C004 1.511(2) . ?
C002 C009 1.392(2) . ?
C003 C005 1.385(2) . ?
C003 C008 1.391(2) . ?
C003 C014 1.505(2) . ?
C004 C006 1.512(2) . ?
C004 C011 1.540(2) . ?
C006 C010 1.388(2) . ?
C006 C013 1.384(2) . ?
C007 O3 1.208(2) . ?
C007 C017 1.494(3) . ?
C007 C011 1.513(2) . ?
C008 C009 1.386(2) . ?
C008 C016 1.513(2) . ?
C010 C021 1.386(3) . ?
C011 C012 1.526(2) . ?
C012 C015 1.504(2) . ?
C013 C018 1.387(3) . ?
C014 C019 1.523(3) . ?
C016 C019 1.524(3) . ?
C018 C020 1.380(3) . ?
C020 C021 1.375(3) . ?

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
C013 O1 C012 119.94(12) . . ?
C002 O2 C012 120.28(12) . . ?
C002 C001 C005 118.86(14) . . ?
C002 C001 C004 118.78(13) . . ?
C005 C001 C004 122.30(13) . . ?
O2 C002 C001 122.30(13) . . ?
O2 C002 C009 116.15(14) . . ?
C001 C002 C009 121.56(14) . . ?
C005 C003 C008 120.14(14) . . ?
C005 C003 C014 128.95(16) . . ?
C008 C003 C014 110.90(15) . . ?
C006 C004 C001 109.94(12) . . ?
C006 C004 C011 107.77(12) . . ?
C001 C004 C011 108.59(11) . . ?
C003 C005 C001 120.21(14) . . ?
C010 C006 C013 118.46(15) . . ?
C010 C006 C004 122.59(15) . . ?
C013 C006 C004 118.94(14) . . ?
O3 C007 C017 121.11(17) . . ?
O3 C007 C011 122.82(17) . . ?
C017 C007 C011 116.07(15) . . ?
C009 C008 C003 120.54(14) . . ?
C009 C008 C016 129.18(16) . . ?
C003 C008 C016 110.23(15) . . ?
C008 C009 C002 118.67(15) . . ?
C021 C010 C006 120.88(18) . . ?
C007 C011 C012 115.58(13) . . ?
C007 C011 C004 111.83(13) . . ?
C012 C011 C004 106.77(13) . . ?
O2 C012 O1 108.34(14) . . ?
O2 C012 C015 105.65(13) . . ?
O1 C012 C015 104.77(14) . . ?
O2 C012 C011 112.74(12) . . ?
O1 C012 C011 109.22(13) . . ?
C015 C012 C011 115.62(16) . . ?
C018 C013 O1 116.56(16) . . ?
C018 C013 C006 121.02(17) . . ?
O1 C013 C006 122.40(15) . . ?
C003 C014 C019 103.71(16) . . ?
C008 C016 C019 103.45(15) . . ?
C013 C018 C020 119.5(2) . . ?
C016 C019 C014 107.16(15) . . ?
C021 C020 C018 120.37(18) . . ?
C020 C021 C010 119.74(19) . . ?

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
C012 O2 C002 C001 -0.5(2) . . . . ?
C012 O2 C002 C009 179.58(15) . . . . ?
C005 C001 C002 O2 179.16(14) . . . . ?
C004 C001 C002 O2 -3.4(2) . . . . ?
C005 C001 C002 C009 -0.9(2) . . . . ?
C004 C001 C002 C009 176.51(14) . . . . ?
C002 C001 C004 C006 -83.54(17) . . . . ?
C005 C001 C004 C006 93.79(17) . . . . ?
C002 C001 C004 C011 34.13(18) . . . . ?
C005 C001 C004 C011 -148.54(14) . . . . ?
C008 C003 C005 C001 -0.1(2) . . . . ?
C014 C003 C005 C001 178.76(16) . . . . ?
C002 C001 C005 C003 1.0(2) . . . . ?
C004 C001 C005 C003 -176.31(14) . . . . ?
C001 C004 C006 C010 -91.75(17) . . . . ?
C011 C004 C006 C010 150.07(14) . . . . ?
C001 C004 C006 C013 87.10(16) . . . . ?
C011 C004 C006 C013 -31.09(18) . . . . ?
C005 C003 C008 C009 -1.0(2) . . . . ?
C014 C003 C008 C009 179.96(15) . . . . ?
C005 C003 C008 C016 176.82(14) . . . . ?
C014 C003 C008 C016 -2.21(19) . . . . ?
C003 C008 C009 C002 1.1(2) . . . . ?
C016 C008 C009 C002 -176.27(16) . . . . ?
O2 C002 C009 C008 179.79(14) . . . . ?
C001 C002 C009 C008 -0.1(2) . . . . ?
C013 C006 C010 C021 0.7(2) . . . . ?
C004 C006 C010 C021 179.52(15) . . . . ?
O3 C007 C011 C012 14.8(2) . . . . ?
C017 C007 C011 C012 -165.91(16) . . . . ?
O3 C007 C011 C004 -107.66(19) . . . . ?
C017 C007 C011 C004 71.66(19) . . . . ?
C006 C004 C011 C007 -172.32(12) . . . . ?
C001 C004 C011 C007 68.64(16) . . . . ?
C006 C004 C011 C012 60.35(14) . . . . ?
C001 C004 C011 C012 -58.70(15) . . . . ?
C002 O2 C012 O1 93.12(17) . . . . ?
C002 O2 C012 C015 -155.06(16) . . . . ?
C002 O2 C012 C011 -27.9(2) . . . . ?
C013 O1 C012 O2 -87.75(17) . . . . ?
C013 O1 C012 C015 159.83(15) . . . . ?
C013 O1 C012 C011 35.40(19) . . . . ?
C007 C011 C012 O2 -67.97(17) . . . . ?
C004 C011 C012 O2 57.11(17) . . . . ?
C007 C011 C012 O1 171.54(13) . . . . ?
C004 C011 C012 O1 -63.38(15) . . . . ?
C007 C011 C012 C015 53.72(19) . . . . ?
C004 C011 C012 C015 178.81(13) . . . . ?
C012 O1 C013 C018 177.77(16) . . . . ?
C012 O1 C013 C006 -4.1(2) . . . . ?
C010 C006 C013 C018 -0.9(2) . . . . ?
C004 C006 C013 C018 -179.84(16) . . . . ?
C010 C006 C013 O1 -179.03(14) . . . . ?
C004 C006 C013 O1 2.1(2) . . . . ?
C005 C003 C014 C019 169.96(18) . . . . ?
C008 C003 C014 C019 -11.1(2) . . . . ?
C009 C008 C016 C019 -167.87(18) . . . . ?
C003 C008 C016 C019 14.5(2) . . . . ?
O1 C013 C018 C020 178.79(18) . . . . ?
C006 C013 C018 C020 0.6(3) . . . . ?
C008 C016 C019 C014 -21.1(2) . . . . ?
C003 C014 C019 C016 19.9(2) . . . . ?
C013 C018 C020 C021 0.0(3) . . . . ?
C018 C020 C021 C010 -0.3(3) . . . . ?
C006 C010 C021 C020 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C011 H011 O3 0.98 2.59 3.2799(19) 127.9 4_556
C015 H01E O3 0.96 2.46 3.045(3) 119.5 .
C017 H01H O3 0.96 2.57 3.486(3) 159.9 4_556

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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 2374533'
loop_
_audit_author_name
_audit_author_address
'Prema Vasudev'
;Central Institute of Medicinal and Aromatic Plants
India
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O3'
_chemical_formula_weight         330.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6299(3)
_cell_length_b                   18.4579(5)
_cell_length_c                   9.9846(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.0090(10)
_cell_angle_gamma                90
_cell_volume                     1667.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    43033
_cell_measurement_theta_min      5.289
_cell_measurement_theta_max      67.778

_exptl_crystal_description       rectangular
_exptl_crystal_colour            \,Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.696
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43033
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.289
_diffrn_reflns_theta_max         67.778
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2981
_reflns_number_gt                2653
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0940P)²+0.4662P] 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         2981
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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
O1 O 0.97182(12) 0.10015(6) 0.47201(12) 0.0427(3) Uani 1 1 d . . . . .
O2 O 0.83148(14) 0.11036(6) 0.23385(12) 0.0477(3) Uani 1 1 d . . . . .
C001 C 1.12060(18) 0.11068(8) 0.50240(16) 0.0401(4) Uani 1 1 d . . . . .
C002 C 0.91172(18) 0.12568(9) 0.14615(16) 0.0427(4) Uani 1 1 d . . . . .
C003 C 1.0693(2) 0.21143(9) 0.32522(19) 0.0482(4) Uani 1 1 d . . . . .
H003 H 1.1140 0.2587 0.3212 0.058 Uiso 1 1 calc R U . . .
C004 C 0.8680(2) 0.08700(9) 0.01574(17) 0.0482(4) Uani 1 1 d . . . . .
O3 O 0.9780(2) 0.23821(8) 0.61393(15) 0.0879(6) Uani 1 1 d . . . . .
C005 C 0.86810(17) 0.14513(8) 0.37034(15) 0.0391(4) Uani 1 1 d . . . . .
C006 C 1.0243(2) 0.17514(9) 0.18140(18) 0.0467(4) Uani 1 1 d . . . . .
C007 C 0.9617(2) 0.26500(9) 0.50075(18) 0.0494(4) Uani 1 1 d . . . . .
C008 C 1.17650(19) 0.16438(9) 0.43703(18) 0.0461(4) Uani 1 1 d . . . . .
C009 C 0.7243(2) -0.00439(12) -0.1452(2) 0.0670(6) Uani 1 1 d . . . . .
H009 H 0.6546 -0.0414 -0.1656 0.080 Uiso 1 1 calc R U . . .
C010 C 0.9399(2) 0.10452(11) -0.08344(18) 0.0568(5) Uani 1 1 d . . . . .
C011 C 1.21328(19) 0.06461(9) 0.60253(18) 0.0485(4) Uani 1 1 d . . . . .
H011 H 1.1744 0.0297 0.6469 0.058 Uiso 1 1 calc R U . . .
C012 C 0.92865(19) 0.22100(8) 0.36437(17) 0.0441(4) Uani 1 1 d . . . . .
H012 H 0.8558 0.2477 0.2870 0.053 Uiso 1 1 calc R U . . .
C013 C 1.0529(2) 0.15671(13) -0.0471(2) 0.0650(6) Uani 1 1 d . . . . .
H013 H 1.0986 0.1688 -0.1125 0.078 Uiso 1 1 calc R U . . .
C014 C 0.7605(2) 0.03152(10) -0.01816(18) 0.0539(5) Uani 1 1 d . . . . .
H014 H 0.7141 0.0193 0.0465 0.065 Uiso 1 1 calc R U . . .
C015 C 1.0966(2) 0.18991(11) 0.0826(2) 0.0575(5) Uani 1 1 d . . . . .
H015 H 1.1747 0.2226 0.1065 0.069 Uiso 1 1 calc R U . . .
C016 C 1.3294(2) 0.16989(12) 0.4746(2) 0.0623(5) Uani 1 1 d . . . . .
H016 H 1.3692 0.2055 0.4325 0.075 Uiso 1 1 calc R U . . .
C017 C 0.72788(19) 0.14289(10) 0.40519(18) 0.0483(4) Uani 1 1 d . . . . .
H01A H 0.6543 0.1727 0.3389 0.072 Uiso 1 1 calc R U . . .
H01B H 0.6928 0.0939 0.3987 0.072 Uiso 1 1 calc R U . . .
H01C H 0.7472 0.1607 0.5002 0.072 Uiso 1 1 calc R U . . .
C018 C 1.3645(2) 0.07098(12) 0.6361(2) 0.0614(5) Uani 1 1 d . . . . .
H018 H 1.4277 0.0396 0.7020 0.074 Uiso 1 1 calc R U . . .
C019 C 0.8954(3) 0.06664(15) -0.2152(2) 0.0740(7) Uani 1 1 d . . . . .
H019 H 0.9387 0.0782 -0.2827 0.089 Uiso 1 1 calc R U . . .
C020 C 1.4221(2) 0.12393(13) 0.5722(2) 0.0695(6) Uani 1 1 d . . . . .
H020 H 1.5239 0.1283 0.5956 0.083 Uiso 1 1 calc R U . . .
C021 C 0.7909(3) 0.01395(16) -0.2448(2) 0.0801(8) Uani 1 1 d . . . . .
H021 H 0.7635 -0.0101 -0.3318 0.096 Uiso 1 1 calc R U . . .
C022 C 0.9738(3) 0.34475(11) 0.4862(3) 0.0699(6) Uani 1 1 d . . . . .
H02A H 0.9576 0.3566 0.3883 0.105 Uiso 1 1 calc R U . . .
H02B H 0.9009 0.3686 0.5163 0.105 Uiso 1 1 calc R U . . .
H02C H 1.0706 0.3605 0.5444 0.105 Uiso 1 1 calc R U . . .


_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 C001 1.3730(19) . ?
O1 C005 1.4224(18) . ?
O2 C002 1.3808(18) . ?
O2 C005 1.4369(18) . ?
C001 C011 1.381(2) . ?
C001 C008 1.392(2) . ?
C002 C006 1.368(2) . ?
C002 C004 1.417(2) . ?
C003 C006 1.508(2) . ?
C003 C008 1.509(2) . ?
C003 C012 1.543(2) . ?
C004 C014 1.412(3) . ?
C004 C010 1.426(2) . ?
O3 C007 1.194(2) . ?
C005 C017 1.506(2) . ?
C005 C012 1.526(2) . ?
C006 C015 1.415(2) . ?
C007 C022 1.488(3) . ?
C007 C012 1.523(2) . ?
C008 C016 1.394(3) . ?
C009 C014 1.367(3) . ?
C009 C021 1.396(4) . ?
C010 C013 1.405(3) . ?
C010 C019 1.421(3) . ?
C011 C018 1.383(3) . ?
C013 C015 1.363(3) . ?
C016 C020 1.368(3) . ?
C018 C020 1.382(3) . ?
C019 C021 1.357(4) . ?

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
C001 O1 C005 120.00(12) . . ?
C002 O2 C005 120.06(12) . . ?
O1 C001 C011 116.09(14) . . ?
O1 C001 C008 122.59(15) . . ?
C011 C001 C008 121.32(16) . . ?
C006 C002 O2 122.66(15) . . ?
C006 C002 C004 122.20(15) . . ?
O2 C002 C004 115.14(15) . . ?
C006 C003 C008 110.48(14) . . ?
C006 C003 C012 107.51(14) . . ?
C008 C003 C012 108.42(13) . . ?
C014 C004 C002 123.27(15) . . ?
C014 C004 C010 119.22(17) . . ?
C002 C004 C010 117.50(18) . . ?
O1 C005 O2 107.50(12) . . ?
O1 C005 C017 106.57(12) . . ?
O2 C005 C017 104.98(13) . . ?
O1 C005 C012 112.28(13) . . ?
O2 C005 C012 110.24(12) . . ?
C017 C005 C012 114.77(13) . . ?
C002 C006 C015 119.01(17) . . ?
C002 C006 C003 119.08(14) . . ?
C015 C006 C003 121.91(17) . . ?
O3 C007 C022 120.88(17) . . ?
O3 C007 C012 123.04(16) . . ?
C022 C007 C012 116.08(16) . . ?
C016 C008 C001 117.92(17) . . ?
C016 C008 C003 123.33(16) . . ?
C001 C008 C003 118.70(15) . . ?
C014 C009 C021 120.6(2) . . ?
C013 C010 C019 122.57(19) . . ?
C013 C010 C004 119.58(17) . . ?
C019 C010 C004 117.8(2) . . ?
C018 C011 C001 119.28(17) . . ?
C007 C012 C005 114.86(13) . . ?
C007 C012 C003 110.75(14) . . ?
C005 C012 C003 106.56(13) . . ?
C015 C013 C010 120.88(16) . . ?
C009 C014 C004 120.50(19) . . ?
C013 C015 C006 120.71(19) . . ?
C020 C016 C008 121.19(19) . . ?
C011 C018 C020 120.22(19) . . ?
C021 C019 C010 121.4(2) . . ?
C016 C020 C018 120.05(18) . . ?
C019 C021 C009 120.4(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
C005 O1 C001 C011 179.92(13) . . . . ?
C005 O1 C001 C008 -0.1(2) . . . . ?
C005 O2 C002 C006 -2.1(2) . . . . ?
C005 O2 C002 C004 178.60(13) . . . . ?
C006 C002 C004 C014 174.66(15) . . . . ?
O2 C002 C004 C014 -6.0(2) . . . . ?
C006 C002 C004 C010 -3.8(2) . . . . ?
O2 C002 C004 C010 175.56(13) . . . . ?
C001 O1 C005 O2 91.48(15) . . . . ?
C001 O1 C005 C017 -156.40(13) . . . . ?
C001 O1 C005 C012 -29.93(18) . . . . ?
C002 O2 C005 O1 -90.89(15) . . . . ?
C002 O2 C005 C017 155.91(14) . . . . ?
C002 O2 C005 C012 31.79(18) . . . . ?
O2 C002 C006 C015 -177.26(14) . . . . ?
C004 C002 C006 C015 2.0(2) . . . . ?
O2 C002 C006 C003 3.7(2) . . . . ?
C004 C002 C006 C003 -177.02(14) . . . . ?
C008 C003 C006 C002 84.21(18) . . . . ?
C012 C003 C006 C002 -33.92(19) . . . . ?
C008 C003 C006 C015 -94.79(18) . . . . ?
C012 C003 C006 C015 147.08(15) . . . . ?
O1 C001 C008 C016 -179.33(15) . . . . ?
C011 C001 C008 C016 0.7(2) . . . . ?
O1 C001 C008 C003 -1.9(2) . . . . ?
C011 C001 C008 C003 178.13(15) . . . . ?
C006 C003 C008 C016 92.2(2) . . . . ?
C012 C003 C008 C016 -150.27(17) . . . . ?
C006 C003 C008 C001 -85.17(18) . . . . ?
C012 C003 C008 C001 32.4(2) . . . . ?
C014 C004 C010 C013 -176.35(16) . . . . ?
C002 C004 C010 C013 2.1(2) . . . . ?
C014 C004 C010 C019 2.3(2) . . . . ?
C002 C004 C010 C019 -179.20(15) . . . . ?
O1 C001 C011 C018 178.57(14) . . . . ?
C008 C001 C011 C018 -1.4(2) . . . . ?
O3 C007 C012 C005 19.2(3) . . . . ?
C022 C007 C012 C005 -161.04(17) . . . . ?
O3 C007 C012 C003 -101.5(2) . . . . ?
C022 C007 C012 C003 78.2(2) . . . . ?
O1 C005 C012 C007 -64.05(17) . . . . ?
O2 C005 C012 C007 176.12(13) . . . . ?
C017 C005 C012 C007 57.86(19) . . . . ?
O1 C005 C012 C003 58.99(16) . . . . ?
O2 C005 C012 C003 -60.84(16) . . . . ?
C017 C005 C012 C003 -179.10(13) . . . . ?
C006 C003 C012 C007 -173.60(13) . . . . ?
C008 C003 C012 C007 66.94(17) . . . . ?
C006 C003 C012 C005 60.82(15) . . . . ?
C008 C003 C012 C005 -58.63(16) . . . . ?
C019 C010 C013 C015 -177.42(17) . . . . ?
C004 C010 C013 C015 1.2(3) . . . . ?
C021 C009 C014 C004 -1.1(3) . . . . ?
C002 C004 C014 C009 -179.25(15) . . . . ?
C010 C004 C014 C009 -0.8(2) . . . . ?
C010 C013 C015 C006 -3.0(3) . . . . ?
C002 C006 C015 C013 1.5(3) . . . . ?
C003 C006 C015 C013 -179.52(16) . . . . ?
C001 C008 C016 C020 0.2(3) . . . . ?
C003 C008 C016 C020 -177.15(18) . . . . ?
C001 C011 C018 C020 1.3(3) . . . . ?
C013 C010 C019 C021 176.71(19) . . . . ?
C004 C010 C019 C021 -1.9(3) . . . . ?
C008 C016 C020 C018 -0.3(3) . . . . ?
C011 C018 C020 C016 -0.5(3) . . . . ?
C010 C019 C021 C009 0.0(3) . . . . ?
C014 C009 C021 C019 1.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C017 H01C O3 0.96 2.56 3.132(3) 118.3 .
C022 H02C O2 0.96 2.63 3.583(3) 171.1 4_666

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045

