# Supplementary Information (SI) for ChemComm.
# 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_5aa
_database_code_depnum_ccdc_archive 'CCDC 2243298'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_publcif_datablock.id            {56b90ed7-7997-4b82-80de-6359957c7730}

# publcif _publ_body_element loop end

_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            'C19 H26 O3'
_chemical_formula_weight         302.40

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   8.7312(11)
_cell_length_b                   16.422(2)
_cell_length_c                   11.2564(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.28

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65854
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.642
_diffrn_reflns_theta_max         26.991
_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             3515
_reflns_number_gt                3313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_max     0.998
_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       'Bruker APEX3'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0679P)²+0.6901P] 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 1488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
C1 C 0.8837(3) 0.5011(2) 0.6182(3) 0.0303(7) Uani 1 1 d . . . . .
H1 H 0.9779 0.5122 0.5754 0.036 Uiso 1 1 calc R U . . .
H10 H 0.9103 0.4885 0.6998 0.036 Uiso 1 1 calc R U . . .
C2 C 0.7619(3) 0.44416(16) 0.4464(2) 0.0196(5) Uani 1 1 d . . . . .
C3 C 0.6477(3) 0.51531(16) 0.4397(2) 0.0204(5) Uani 1 1 d . . . . .
H14 H 0.6255 0.5256 0.3557 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4964(3) 0.49331(15) 0.5012(2) 0.0183(5) Uani 1 1 d . . . . .
H15 H 0.5165 0.4857 0.5862 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3803(3) 0.56174(16) 0.4870(3) 0.0222(6) Uani 1 1 d . . . . .
C6 C 0.3210(4) 0.60182(19) 0.5849(3) 0.0284(7) Uani 1 1 d . . . . .
H19 H 0.3549 0.5882 0.6607 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2101(4) 0.6630(2) 0.5707(4) 0.0375(8) Uani 1 1 d . . . . .
H18 H 0.1701 0.6892 0.6370 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1604(4) 0.68409(19) 0.4589(4) 0.0396(8) Uani 1 1 d . . . . .
H2 H 0.0860 0.7242 0.4497 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4466(4) 0.28290(18) 0.6256(3) 0.0291(6) Uani 1 1 d . . . . .
H3 H 0.4767 0.2635 0.7036 0.035 Uiso 1 1 calc R U . . .
H26 H 0.4030 0.2374 0.5823 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3269(4) 0.3492(2) 0.6390(3) 0.0322(7) Uani 1 1 d . . . . .
H4 H 0.3658 0.3918 0.6904 0.039 Uiso 1 1 calc R U . . .
H25 H 0.2355 0.3267 0.6754 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2867(3) 0.38495(18) 0.5177(3) 0.0271(6) Uani 1 1 d . . . . .
H24 H 0.2179 0.4307 0.5281 0.033 Uiso 1 1 calc R U . . .
H5 H 0.2342 0.3441 0.4706 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4316(3) 0.41349(15) 0.4510(3) 0.0197(5) Uani 1 1 d . . . . .
H6 H 0.4019 0.4240 0.3684 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5505(3) 0.34426(15) 0.4493(3) 0.0191(5) Uani 1 1 d . . . . .
C14 C 0.5038(3) 0.27769(16) 0.3618(3) 0.0244(6) Uani 1 1 d . . . . .
H9 H 0.5848 0.2384 0.3555 0.037 Uiso 1 1 calc R U . . .
H7 H 0.4849 0.3015 0.2853 0.037 Uiso 1 1 calc R U . . .
H8 H 0.4125 0.2514 0.3897 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7836(4) 0.5763(2) 0.6160(3) 0.0328(7) Uani 1 1 d . . . . .
H11 H 0.8425 0.6229 0.6424 0.039 Uiso 1 1 calc R U . . .
H12 H 0.6985 0.5691 0.6703 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7222(3) 0.59219(17) 0.4910(3) 0.0269(6) Uani 1 1 d . . . . .
H20 H 0.8055 0.6093 0.4398 0.032 Uiso 1 1 calc R U . . .
H13 H 0.6473 0.6358 0.4938 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3305(4) 0.58524(18) 0.3744(3) 0.0275(6) Uani 1 1 d . . . . .
H16 H 0.3713 0.5600 0.3076 0.033 Uiso 1 1 calc R U . . .
C18 C 0.2209(4) 0.64587(18) 0.3605(4) 0.0369(8) Uani 1 1 d . . . . .
H17 H 0.1883 0.6606 0.2848 0.044 Uiso 1 1 calc R U . . .
C19 C 0.8991(3) 0.45551(18) 0.3647(3) 0.0271(6) Uani 1 1 d . . . . .
H21 H 0.9664 0.4096 0.3720 0.041 Uiso 1 1 calc R U . . .
H23 H 0.9530 0.5042 0.3865 0.041 Uiso 1 1 calc R U . . .
H22 H 0.8645 0.4599 0.2840 0.041 Uiso 1 1 calc R U . . .
O1 O 0.8094(2) 0.43187(12) 0.56583(18) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.6959(2) 0.37047(11) 0.40622(18) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.5791(2) 0.31240(12) 0.56369(18) 0.0247(4) 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 1.436(4) . ?
C1 C15 1.513(5) . ?
C1 H1 0.9700 . ?
C1 H10 0.9700 . ?
C2 O2 1.414(3) . ?
C2 O1 1.422(3) . ?
C2 C19 1.522(4) . ?
C2 C3 1.538(4) . ?
C3 C16 1.533(4) . ?
C3 C4 1.535(4) . ?
C3 H14 0.9800 . ?
C4 C5 1.522(4) . ?
C4 C12 1.536(3) . ?
C4 H15 0.9800 . ?
C5 C6 1.384(4) . ?
C5 C17 1.394(4) . ?
C6 C7 1.404(5) . ?
C6 H19 0.9300 . ?
C7 C8 1.376(6) . ?
C7 H18 0.9300 . ?
C8 C18 1.378(6) . ?
C8 H2 0.9300 . ?
C9 O3 1.435(3) . ?
C9 C10 1.517(5) . ?
C9 H3 0.9700 . ?
C9 H26 0.9700 . ?
C10 C11 1.528(5) . ?
C10 H4 0.9700 . ?
C10 H25 0.9700 . ?
C11 C12 1.544(4) . ?
C11 H24 0.9700 . ?
C11 H5 0.9700 . ?
C12 C13 1.539(3) . ?
C12 H6 0.9800 . ?
C13 O3 1.412(3) . ?
C13 O2 1.426(3) . ?
C13 C14 1.527(4) . ?
C14 H9 0.9600 . ?
C14 H7 0.9600 . ?
C14 H8 0.9600 . ?
C15 C16 1.528(5) . ?
C15 H11 0.9700 . ?
C15 H12 0.9700 . ?
C16 H20 0.9700 . ?
C16 H13 0.9700 . ?
C17 C18 1.390(4) . ?
C17 H16 0.9300 . ?
C18 H17 0.9300 . ?
C19 H21 0.9600 . ?
C19 H23 0.9600 . ?
C19 H22 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
O1 C1 C15 112.2(2) . . ?
O1 C1 H1 109.2 . . ?
C15 C1 H1 109.2 . . ?
O1 C1 H10 109.2 . . ?
C15 C1 H10 109.2 . . ?
H1 C1 H10 107.9 . . ?
O2 C2 O1 107.4(2) . . ?
O2 C2 C19 103.4(2) . . ?
O1 C2 C19 111.1(2) . . ?
O2 C2 C3 111.7(2) . . ?
O1 C2 C3 110.1(2) . . ?
C19 C2 C3 112.8(2) . . ?
C16 C3 C4 112.9(2) . . ?
C16 C3 C2 109.4(2) . . ?
C4 C3 C2 110.9(2) . . ?
C16 C3 H14 107.8 . . ?
C4 C3 H14 107.8 . . ?
C2 C3 H14 107.8 . . ?
C5 C4 C12 110.2(2) . . ?
C5 C4 C3 110.6(2) . . ?
C12 C4 C3 110.6(2) . . ?
C5 C4 H15 108.4 . . ?
C12 C4 H15 108.4 . . ?
C3 C4 H15 108.4 . . ?
C6 C5 C17 118.4(3) . . ?
C6 C5 C4 121.1(3) . . ?
C17 C5 C4 120.5(3) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H19 119.8 . . ?
C7 C6 H19 119.8 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H18 119.9 . . ?
C6 C7 H18 119.9 . . ?
C7 C8 C18 120.0(3) . . ?
C7 C8 H2 120.0 . . ?
C18 C8 H2 120.0 . . ?
O3 C9 C10 111.2(2) . . ?
O3 C9 H3 109.4 . . ?
C10 C9 H3 109.4 . . ?
O3 C9 H26 109.4 . . ?
C10 C9 H26 109.4 . . ?
H3 C9 H26 108.0 . . ?
C9 C10 C11 110.2(3) . . ?
C9 C10 H4 109.6 . . ?
C11 C10 H4 109.6 . . ?
C9 C10 H25 109.6 . . ?
C11 C10 H25 109.6 . . ?
H4 C10 H25 108.1 . . ?
C10 C11 C12 111.3(2) . . ?
C10 C11 H24 109.4 . . ?
C12 C11 H24 109.4 . . ?
C10 C11 H5 109.4 . . ?
C12 C11 H5 109.4 . . ?
H24 C11 H5 108.0 . . ?
C4 C12 C13 112.7(2) . . ?
C4 C12 C11 112.4(2) . . ?
C13 C12 C11 109.5(2) . . ?
C4 C12 H6 107.3 . . ?
C13 C12 H6 107.3 . . ?
C11 C12 H6 107.3 . . ?
O3 C13 O2 105.3(2) . . ?
O3 C13 C14 111.7(2) . . ?
O2 C13 C14 103.5(2) . . ?
O3 C13 C12 112.5(2) . . ?
O2 C13 C12 112.4(2) . . ?
C14 C13 C12 110.9(2) . . ?
C13 C14 H9 109.5 . . ?
C13 C14 H7 109.5 . . ?
H9 C14 H7 109.5 . . ?
C13 C14 H8 109.5 . . ?
H9 C14 H8 109.5 . . ?
H7 C14 H8 109.5 . . ?
C1 C15 C16 111.0(3) . . ?
C1 C15 H11 109.4 . . ?
C16 C15 H11 109.4 . . ?
C1 C15 H12 109.4 . . ?
C16 C15 H12 109.4 . . ?
H11 C15 H12 108.0 . . ?
C15 C16 C3 110.8(2) . . ?
C15 C16 H20 109.5 . . ?
C3 C16 H20 109.5 . . ?
C15 C16 H13 109.5 . . ?
C3 C16 H13 109.5 . . ?
H20 C16 H13 108.1 . . ?
C18 C17 C5 121.0(3) . . ?
C18 C17 H16 119.5 . . ?
C5 C17 H16 119.5 . . ?
C8 C18 C17 120.0(3) . . ?
C8 C18 H17 120.0 . . ?
C17 C18 H17 120.0 . . ?
C2 C19 H21 109.5 . . ?
C2 C19 H23 109.5 . . ?
H21 C19 H23 109.5 . . ?
C2 C19 H22 109.5 . . ?
H21 C19 H22 109.5 . . ?
H23 C19 H22 109.5 . . ?
C2 O1 C1 114.1(2) . . ?
C2 O2 C13 120.8(2) . . ?
C13 O3 C9 115.2(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
O2 C2 C3 C16 176.7(2) . . . . ?
O1 C2 C3 C16 57.4(3) . . . . ?
C19 C2 C3 C16 -67.2(3) . . . . ?
O2 C2 C3 C4 51.5(3) . . . . ?
O1 C2 C3 C4 -67.8(3) . . . . ?
C19 C2 C3 C4 167.6(2) . . . . ?
C16 C3 C4 C5 60.6(3) . . . . ?
C2 C3 C4 C5 -176.1(2) . . . . ?
C16 C3 C4 C12 -176.9(2) . . . . ?
C2 C3 C4 C12 -53.7(3) . . . . ?
C12 C4 C5 C6 118.5(3) . . . . ?
C3 C4 C5 C6 -118.9(3) . . . . ?
C12 C4 C5 C17 -61.2(3) . . . . ?
C3 C4 C5 C17 61.4(3) . . . . ?
C17 C5 C6 C7 1.9(4) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C6 C7 C8 C18 -0.7(5) . . . . ?
O3 C9 C10 C11 54.8(3) . . . . ?
C9 C10 C11 C12 -53.4(3) . . . . ?
C5 C4 C12 C13 173.3(2) . . . . ?
C3 C4 C12 C13 50.6(3) . . . . ?
C5 C4 C12 C11 -62.3(3) . . . . ?
C3 C4 C12 C11 175.0(2) . . . . ?
C10 C11 C12 C4 -74.9(3) . . . . ?
C10 C11 C12 C13 51.3(3) . . . . ?
C4 C12 C13 O3 74.2(3) . . . . ?
C11 C12 C13 O3 -51.8(3) . . . . ?
C4 C12 C13 O2 -44.5(3) . . . . ?
C11 C12 C13 O2 -170.5(2) . . . . ?
C4 C12 C13 C14 -159.9(2) . . . . ?
C11 C12 C13 C14 74.1(3) . . . . ?
O1 C1 C15 C16 -51.7(3) . . . . ?
C1 C15 C16 C3 51.2(3) . . . . ?
C4 C3 C16 C15 70.2(3) . . . . ?
C2 C3 C16 C15 -53.9(3) . . . . ?
C6 C5 C17 C18 -1.8(4) . . . . ?
C4 C5 C17 C18 177.9(3) . . . . ?
C7 C8 C18 C17 0.9(5) . . . . ?
C5 C17 C18 C8 0.4(5) . . . . ?
O2 C2 O1 C1 178.1(2) . . . . ?
C19 C2 O1 C1 65.6(3) . . . . ?
C3 C2 O1 C1 -60.0(3) . . . . ?
C15 C1 O1 C2 57.5(3) . . . . ?
O1 C2 O2 C13 71.6(3) . . . . ?
C19 C2 O2 C13 -170.9(2) . . . . ?
C3 C2 O2 C13 -49.2(3) . . . . ?
O3 C13 O2 C2 -77.3(3) . . . . ?
C14 C13 O2 C2 165.3(2) . . . . ?
C12 C13 O2 C2 45.5(3) . . . . ?
O2 C13 O3 C9 179.2(2) . . . . ?
C14 C13 O3 C9 -69.0(3) . . . . ?
C12 C13 O3 C9 56.4(3) . . . . ?
C10 C9 O3 C13 -57.7(3) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_5as
_database_code_depnum_ccdc_archive 'CCDC 2243299'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 Cl O3'
_chemical_formula_sum            'C19 H25 Cl O3'
_chemical_formula_weight         336.84
_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'
Cl Cl 0.1484 0.1585 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.719(3)
_cell_length_b                   12.729(2)
_cell_length_c                   8.8925(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1666.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0961 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1605
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            54108
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1612
_reflns_number_total             1885
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.949
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0903
_refine_ls_restrained_S_all      1.152
_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)+(0.0638P)²+8.3943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5380(4) 0.750000 0.1959(7) 0.0211(12) Uani 1 2 d S T P . .
C2 C 0.4436(4) 0.750000 0.1907(6) 0.0190(11) Uani 1 2 d S T P . .
H2 H 0.411470 0.750000 0.098003 0.023 Uiso 1 2 calc R U P . .
C3 C 0.3982(4) 0.750000 0.3292(6) 0.0191(11) Uani 1 2 d S T P . .
H3 H 0.333677 0.750000 0.329945 0.023 Uiso 1 2 calc R U P . .
C4 C 0.4443(4) 0.750000 0.4656(6) 0.0156(11) Uani 1 2 d S T P . .
C5 C 0.5377(4) 0.750000 0.4623(7) 0.0187(11) Uani 1 2 d S T P . .
H5 H 0.570461 0.750000 0.554286 0.022 Uiso 1 2 calc R U P . .
C6 C 0.5851(4) 0.750000 0.3275(7) 0.0210(12) Uani 1 2 d S T P . .
H6 H 0.649605 0.750000 0.327077 0.025 Uiso 1 2 calc R U P . .
C7 C 0.3919(3) 0.750000 0.6126(6) 0.0133(10) Uani 1 2 d S T P . .
H7 H 0.437117 0.750000 0.696523 0.016 Uiso 1 2 calc R U P . .
C8 C 0.3334(2) 0.6506(3) 0.6282(4) 0.0134(7) Uani 1 1 d . . . . .
H8 H 0.290086 0.648824 0.541618 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3904(3) 0.5498(3) 0.6228(4) 0.0154(8) Uani 1 1 d . . . . .
H9A H 0.349640 0.488299 0.613682 0.018 Uiso 1 1 calc R U . . .
H9B H 0.430230 0.551409 0.533050 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4486(3) 0.5385(3) 0.7639(5) 0.0210(9) Uani 1 1 d . . . . .
H10A H 0.480314 0.469890 0.762892 0.025 Uiso 1 1 calc R U . . .
H10B H 0.494942 0.594813 0.766944 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3873(3) 0.5459(3) 0.9019(4) 0.0204(8) Uani 1 1 d . . . . .
H11A H 0.346223 0.484354 0.904355 0.024 Uiso 1 1 calc R U . . .
H11B H 0.425205 0.544127 0.993868 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2772(2) 0.6526(3) 0.7738(4) 0.0150(8) Uani 1 1 d . . . . .
C13 C 0.2009(3) 0.5729(3) 0.7715(4) 0.0190(8) Uani 1 1 d . . . . .
H13A H 0.164493 0.579890 0.863180 0.028 Uiso 1 1 calc R U . . .
H13B H 0.226517 0.501872 0.766353 0.028 Uiso 1 1 calc R U . . .
H13C H 0.162334 0.585183 0.683411 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59775(11) 0.750000 0.02351(17) 0.0276(4) Uani 1 2 d S T P . .
O1 O 0.33468(18) 0.6395(2) 0.9011(3) 0.0166(6) Uani 1 1 d . . . . .
O2 O 0.2317(2) 0.750000 0.7937(4) 0.0163(8) Uani 1 2 d S T P . .


_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 1.391(9) . ?
C1 C6 1.359(9) . ?
C1 Cl1 1.767(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(8) . ?
C4 C5 1.375(8) . ?
C4 C7 1.518(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(8) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.537(4) . ?
C7 C8 1.537(4) 7_575 ?
C8 H8 1.0000 . ?
C8 C9 1.533(5) . ?
C8 C12 1.536(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O1 1.421(5) . ?
C12 C13 1.514(5) . ?
C12 O1 1.423(4) . ?
C12 O2 1.420(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 117.9(5) . . ?
C6 C1 C2 122.5(5) . . ?
C6 C1 Cl1 119.6(5) . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.5(5) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C7 120.2(5) . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 C7 121.8(5) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(6) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7 107.8 . . ?
C4 C7 C8 111.3(3) . . ?
C4 C7 C8 111.3(3) . 7_575 ?
C8 C7 H7 107.8 . . ?
C8 C7 H7 107.8 7_575 . ?
C8 C7 C8 110.8(4) 7_575 . ?
C7 C8 H8 107.8 . . ?
C9 C8 C7 112.3(3) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C12 109.6(3) . . ?
C12 C8 C7 111.3(3) . . ?
C12 C8 H8 107.8 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(3) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 108.9(3) . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O1 C11 C10 111.7(3) . . ?
O1 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C13 C12 C8 112.1(3) . . ?
O1 C12 C8 110.4(3) . . ?
O1 C12 C13 111.9(3) . . ?
O2 C12 C8 111.9(3) . . ?
O2 C12 C13 103.7(3) . . ?
O2 C12 O1 106.5(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O1 C12 115.2(3) . . ?
C12 O2 C12 121.6(4) . 7_575 ?

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
C1 C2 C3 C4 0.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C2 C3 C4 C7 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C7 C8 -62.1(3) . . . 7_575 ?
C3 C4 C7 C8 62.1(3) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C7 C8 C9 59.1(5) . . . . ?
C4 C7 C8 C12 -177.6(3) . . . . ?
C5 C4 C7 C8 -117.9(3) . . . . ?
C5 C4 C7 C8 117.9(3) . . . 7_575 ?
C6 C1 C2 C3 0.000(1) . . . . ?
C7 C4 C5 C6 180.000(1) . . . . ?
C7 C8 C9 C10 69.8(4) . . . . ?
C7 C8 C12 C13 164.0(3) . . . . ?
C7 C8 C12 O1 -70.5(4) . . . . ?
C7 C8 C12 O2 47.9(4) . . . . ?
C8 C7 C8 C9 -176.5(3) 7_575 . . . ?
C8 C7 C8 C12 -53.2(5) 7_575 . . . ?
C8 C9 C10 C11 54.1(4) . . . . ?
C8 C12 O1 C11 -57.8(4) . . . . ?
C8 C12 O2 C12 -46.9(5) . . . 7_575 ?
C9 C8 C12 C13 -71.2(4) . . . . ?
C9 C8 C12 O1 54.3(4) . . . . ?
C9 C8 C12 O2 172.7(3) . . . . ?
C9 C10 C11 O1 -54.6(4) . . . . ?
C10 C11 O1 C12 58.5(4) . . . . ?
C12 C8 C9 C10 -54.5(4) . . . . ?
C13 C12 O1 C11 67.9(4) . . . . ?
C13 C12 O2 C12 -168.0(3) . . . 7_575 ?
Cl1 C1 C2 C3 180.000(0) . . . . ?
Cl1 C1 C6 C5 180.000(1) . . . . ?
O1 C12 O2 C12 73.8(5) . . . 7_575 ?
O2 C12 O1 C11 -179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT097_5as                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.95 eA-3  
RESPONSE: There is no disorder in the molecule, and also we have assigned 
the atoms appropriately. Still, there is a positive residual desity close to 
chlorine atom, when that electron density taken into the consideration, its 
interupting the real geometry of the molecule, hence, we have not taken 
into the consideration.  
;
# end Validation Reply Form
####################################################################### 
# 
# 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_6fs
_database_code_depnum_ccdc_archive 'CCDC 2243301'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_publcif_datablock.id            {7dc0a681-f822-4d08-8c59-1a28f5771bd8}

# publcif _publ_body_element loop end

_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            'C30 H36 Cl2 O3'
_chemical_formula_weight         515.49

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'
Cl Cl 0.1484 0.1585 '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                   10.1704(10)
_cell_length_b                   12.2125(13)
_cell_length_c                   12.2391(13)
_cell_angle_alpha                66.671(4)
_cell_angle_beta                 78.351(4)
_cell_angle_gamma                87.561(4)
_cell_volume                     1366.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.84

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67475
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5946
_reflns_number_gt                4719
_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 APEX3'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0469P)²+1.0439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0171(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5946
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_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 0.64841(19) 0.53886(17) 0.26815(17) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.53194(19) 0.50336(18) 0.22479(17) 0.0149(4) Uani 1 1 d . . . . .
H32 H 0.4838 0.5743 0.1873 0.018 Uiso 1 1 calc R U . . .
H25 H 0.5690 0.4737 0.1627 0.018 Uiso 1 1 calc R U . . .
C3 C 0.43149(18) 0.40861(17) 0.32438(17) 0.0138(4) Uani 1 1 d . . . . .
H33 H 0.4080 0.4305 0.3937 0.017 Uiso 1 1 calc R U . . .
H24 H 0.4750 0.3329 0.3504 0.017 Uiso 1 1 calc R U . . .
C4 C 0.30028(18) 0.39147(17) 0.28544(17) 0.0129(4) Uani 1 1 d . . . . .
C5 C 0.18945(19) 0.47641(17) 0.30858(18) 0.0140(4) Uani 1 1 d . . . . .
H8 H 0.1574 0.4429 0.3969 0.017 Uiso 1 1 calc R U . . .
C6 C 0.06647(19) 0.46683(18) 0.25690(19) 0.0164(4) Uani 1 1 d . . . . .
H19 H -0.0113 0.4953 0.2970 0.020 Uiso 1 1 calc R U . . .
H18 H 0.0827 0.5176 0.1709 0.020 Uiso 1 1 calc R U . . .
C7 C 0.03699(19) 0.34136(18) 0.27392(18) 0.0149(4) Uani 1 1 d . . . . .
C8 C -0.1036(2) 0.22566(18) 0.21739(19) 0.0167(4) Uani 1 1 d . . . . .
C9 C -0.0135(2) 0.2301(2) 0.1008(2) 0.0239(5) Uani 1 1 d . . . . .
H10 H -0.0313 0.2997 0.0339 0.036 Uiso 1 1 calc R U . . .
H2 H -0.0310 0.1600 0.0879 0.036 Uiso 1 1 calc R U . . .
H9 H 0.0788 0.2334 0.1067 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1889(2) 0.12714(18) 0.74979(18) 0.0188(4) Uani 1 1 d . . . . .
C11 C 0.0857(2) 0.18802(18) 0.69577(19) 0.0182(4) Uani 1 1 d . . . . .
H36 H 0.0065 0.1993 0.7428 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1022(2) 0.23194(18) 0.57018(18) 0.0167(4) Uani 1 1 d . . . . .
H35 H 0.0328 0.2722 0.5336 0.020 Uiso 1 1 calc R U . . .
C13 C 0.22043(19) 0.21713(17) 0.49767(18) 0.0140(4) Uani 1 1 d . . . . .
C14 C 0.32164(19) 0.15410(17) 0.55574(18) 0.0151(4) Uani 1 1 d . . . . .
H3 H 0.4007 0.1418 0.5093 0.018 Uiso 1 1 calc R U . . .
C15 C 0.3070(2) 0.10940(18) 0.68103(19) 0.0177(4) Uani 1 1 d . . . . .
H4 H 0.3756 0.0681 0.7183 0.021 Uiso 1 1 calc R U . . .
C16 C 0.23804(18) 0.26142(17) 0.35996(17) 0.0131(4) Uani 1 1 d . . . . .
H34 H 0.3016 0.2087 0.3355 0.016 Uiso 1 1 calc R U . . .
C17 C 0.33699(18) 0.40677(17) 0.15194(18) 0.0141(4) Uani 1 1 d . . . . .
C18 C 0.4156(2) 0.31057(18) 0.12204(18) 0.0176(4) Uani 1 1 d . . . . .
H5 H 0.3544 0.2510 0.1256 0.026 Uiso 1 1 calc R U . . .
H7 H 0.4723 0.2744 0.1798 0.026 Uiso 1 1 calc R U . . .
H6 H 0.4701 0.3454 0.0418 0.026 Uiso 1 1 calc R U . . .
C19 C -0.0790(2) 0.11990(18) 0.32915(19) 0.0186(4) Uani 1 1 d . . . . .
H11 H -0.0980 0.0462 0.3218 0.022 Uiso 1 1 calc R U . . .
H14 H -0.1391 0.1216 0.4009 0.022 Uiso 1 1 calc R U . . .
C20 C 0.0664(2) 0.12366(18) 0.34304(19) 0.0176(4) Uani 1 1 d . . . . .
H12 H 0.0749 0.0692 0.4241 0.021 Uiso 1 1 calc R U . . .
H13 H 0.1246 0.0980 0.2851 0.021 Uiso 1 1 calc R U . . .
C21 C 0.10927(19) 0.24791(17) 0.32183(17) 0.0139(4) Uani 1 1 d . . . . .
C22 C -0.2503(2) 0.2295(2) 0.2067(2) 0.0217(5) Uani 1 1 d . . . . .
H17 H -0.3062 0.2239 0.2822 0.033 Uiso 1 1 calc R U . . .
H16 H -0.2723 0.1639 0.1884 0.033 Uiso 1 1 calc R U . . .
H15 H -0.2648 0.3033 0.1429 0.033 Uiso 1 1 calc R U . . .
C23 C 0.23067(19) 0.60545(17) 0.27667(18) 0.0150(4) Uani 1 1 d . . . . .
C24 C 0.2467(2) 0.63937(19) 0.3696(2) 0.0188(4) Uani 1 1 d . . . . .
H20 H 0.2304 0.5829 0.4492 0.023 Uiso 1 1 calc R U . . .
C25 C 0.2865(2) 0.75583(19) 0.3463(2) 0.0227(5) Uani 1 1 d . . . . .
H23 H 0.2963 0.7772 0.4093 0.027 Uiso 1 1 calc R U . . .
C26 C 0.3109(2) 0.83856(19) 0.2277(2) 0.0231(5) Uani 1 1 d . . . . .
C27 C 0.2934(2) 0.80927(19) 0.1333(2) 0.0230(5) Uani 1 1 d . . . . .
H22 H 0.3083 0.8666 0.0541 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2535(2) 0.69359(18) 0.15804(19) 0.0189(4) Uani 1 1 d . . . . .
H21 H 0.2416 0.6738 0.0946 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6019(2) 0.61402(19) 0.34053(19) 0.0194(4) Uani 1 1 d . . . . .
H27 H 0.5300 0.5719 0.4070 0.029 Uiso 1 1 calc R U . . .
H26 H 0.5707 0.6882 0.2890 0.029 Uiso 1 1 calc R U . . .
H28 H 0.6753 0.6297 0.3714 0.029 Uiso 1 1 calc R U . . .
C30 C 0.75628(19) 0.60875(19) 0.15800(18) 0.0177(4) Uani 1 1 d . . . . .
H31 H 0.8277 0.6344 0.1842 0.027 Uiso 1 1 calc R U . . .
H29 H 0.7180 0.6772 0.1045 0.027 Uiso 1 1 calc R U . . .
H30 H 0.7911 0.5587 0.1159 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.16961(6) 0.07094(5) 0.90685(5) 0.02692(15) Uani 1 1 d . . . . .
Cl2 Cl 0.36492(6) 0.98417(5) 0.19575(7) 0.03466(17) Uani 1 1 d . . . . .
H1 H 0.759(3) 0.404(3) 0.308(3) 0.052 Uiso 1 1 d . U . . .
O1 O 0.70334(14) 0.43427(13) 0.34827(13) 0.0177(3) Uani 1 1 d . . . . .
O2 O -0.07869(13) 0.33557(12) 0.23259(13) 0.0163(3) Uani 1 1 d . . . . .
O3 O 0.30809(14) 0.49466(13) 0.07028(13) 0.0184(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 1.440(2) . ?
C1 C29 1.513(3) . ?
C1 C30 1.523(3) . ?
C1 C2 1.534(3) . ?
C2 C3 1.533(3) . ?
C2 H32 0.9700 . ?
C2 H25 0.9700 . ?
C3 C4 1.553(3) . ?
C3 H33 0.9700 . ?
C3 H24 0.9700 . ?
C4 C17 1.537(3) . ?
C4 C5 1.559(3) . ?
C4 C16 1.568(3) . ?
C5 C23 1.521(3) . ?
C5 C6 1.539(3) . ?
C5 H8 0.9800 . ?
C6 C7 1.497(3) . ?
C6 H19 0.9700 . ?
C6 H18 0.9700 . ?
C7 C21 1.326(3) . ?
C7 O2 1.386(2) . ?
C8 O2 1.465(2) . ?
C8 C9 1.515(3) . ?
C8 C22 1.520(3) . ?
C8 C19 1.521(3) . ?
C9 H10 0.9600 . ?
C9 H2 0.9600 . ?
C9 H9 0.9600 . ?
C10 C15 1.383(3) . ?
C10 C11 1.384(3) . ?
C10 Cl1 1.738(2) . ?
C11 C12 1.389(3) . ?
C11 H36 0.9300 . ?
C12 C13 1.394(3) . ?
C12 H35 0.9300 . ?
C13 C14 1.397(3) . ?
C13 C16 1.526(3) . ?
C14 C15 1.387(3) . ?
C14 H3 0.9300 . ?
C15 H4 0.9300 . ?
C16 C21 1.512(3) . ?
C16 H34 0.9800 . ?
C17 O3 1.216(2) . ?
C17 C18 1.515(3) . ?
C18 H5 0.9600 . ?
C18 H7 0.9600 . ?
C18 H6 0.9600 . ?
C19 C20 1.527(3) . ?
C19 H11 0.9700 . ?
C19 H14 0.9700 . ?
C20 C21 1.503(3) . ?
C20 H12 0.9700 . ?
C20 H13 0.9700 . ?
C22 H17 0.9600 . ?
C22 H16 0.9600 . ?
C22 H15 0.9600 . ?
C23 C24 1.394(3) . ?
C23 C28 1.403(3) . ?
C24 C25 1.396(3) . ?
C24 H20 0.9300 . ?
C25 C26 1.380(3) . ?
C25 H23 0.9300 . ?
C26 C27 1.382(3) . ?
C26 Cl2 1.750(2) . ?
C27 C28 1.383(3) . ?
C27 H22 0.9300 . ?
C28 H21 0.9300 . ?
C29 H27 0.9600 . ?
C29 H26 0.9600 . ?
C29 H28 0.9600 . ?
C30 H31 0.9600 . ?
C30 H29 0.9600 . ?
C30 H30 0.9600 . ?
O1 H1 0.85(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
O1 C1 C29 106.16(16) . . ?
O1 C1 C30 110.28(16) . . ?
C29 C1 C30 109.52(16) . . ?
O1 C1 C2 110.37(15) . . ?
C29 C1 C2 111.50(16) . . ?
C30 C1 C2 108.99(16) . . ?
C3 C2 C1 115.01(16) . . ?
C3 C2 H32 108.5 . . ?
C1 C2 H32 108.5 . . ?
C3 C2 H25 108.5 . . ?
C1 C2 H25 108.5 . . ?
H32 C2 H25 107.5 . . ?
C2 C3 C4 114.49(16) . . ?
C2 C3 H33 108.6 . . ?
C4 C3 H33 108.6 . . ?
C2 C3 H24 108.6 . . ?
C4 C3 H24 108.6 . . ?
H33 C3 H24 107.6 . . ?
C17 C4 C3 107.86(15) . . ?
C17 C4 C5 113.08(16) . . ?
C3 C4 C5 112.24(15) . . ?
C17 C4 C16 106.40(15) . . ?
C3 C4 C16 111.12(15) . . ?
C5 C4 C16 106.01(15) . . ?
C23 C5 C6 112.06(16) . . ?
C23 C5 C4 118.27(15) . . ?
C6 C5 C4 110.98(15) . . ?
C23 C5 H8 104.7 . . ?
C6 C5 H8 104.7 . . ?
C4 C5 H8 104.7 . . ?
C7 C6 C5 112.06(16) . . ?
C7 C6 H19 109.2 . . ?
C5 C6 H19 109.2 . . ?
C7 C6 H18 109.2 . . ?
C5 C6 H18 109.2 . . ?
H19 C6 H18 107.9 . . ?
C21 C7 O2 124.01(18) . . ?
C21 C7 C6 125.82(18) . . ?
O2 C7 C6 110.17(16) . . ?
O2 C8 C9 108.41(16) . . ?
O2 C8 C22 104.34(16) . . ?
C9 C8 C22 110.42(17) . . ?
O2 C8 C19 108.42(16) . . ?
C9 C8 C19 113.06(18) . . ?
C22 C8 C19 111.75(17) . . ?
C8 C9 H10 109.5 . . ?
C8 C9 H2 109.5 . . ?
H10 C9 H2 109.5 . . ?
C8 C9 H9 109.5 . . ?
H10 C9 H9 109.5 . . ?
H2 C9 H9 109.5 . . ?
C15 C10 C11 121.18(19) . . ?
C15 C10 Cl1 119.27(17) . . ?
C11 C10 Cl1 119.56(16) . . ?
C10 C11 C12 118.92(19) . . ?
C10 C11 H36 120.5 . . ?
C12 C11 H36 120.5 . . ?
C11 C12 C13 121.59(19) . . ?
C11 C12 H35 119.2 . . ?
C13 C12 H35 119.2 . . ?
C12 C13 C14 117.73(18) . . ?
C12 C13 C16 122.05(17) . . ?
C14 C13 C16 120.14(17) . . ?
C15 C14 C13 121.55(18) . . ?
C15 C14 H3 119.2 . . ?
C13 C14 H3 119.2 . . ?
C10 C15 C14 119.02(19) . . ?
C10 C15 H4 120.5 . . ?
C14 C15 H4 120.5 . . ?
C21 C16 C13 112.15(15) . . ?
C21 C16 C4 109.99(16) . . ?
C13 C16 C4 115.55(15) . . ?
C21 C16 H34 106.2 . . ?
C13 C16 H34 106.2 . . ?
C4 C16 H34 106.2 . . ?
O3 C17 C18 119.57(18) . . ?
O3 C17 C4 122.04(18) . . ?
C18 C17 C4 118.37(17) . . ?
C17 C18 H5 109.5 . . ?
C17 C18 H7 109.5 . . ?
H5 C18 H7 109.5 . . ?
C17 C18 H6 109.5 . . ?
H5 C18 H6 109.5 . . ?
H7 C18 H6 109.5 . . ?
C8 C19 C20 110.61(16) . . ?
C8 C19 H11 109.5 . . ?
C20 C19 H11 109.5 . . ?
C8 C19 H14 109.5 . . ?
C20 C19 H14 109.5 . . ?
H11 C19 H14 108.1 . . ?
C21 C20 C19 110.43(17) . . ?
C21 C20 H12 109.6 . . ?
C19 C20 H12 109.6 . . ?
C21 C20 H13 109.6 . . ?
C19 C20 H13 109.6 . . ?
H12 C20 H13 108.1 . . ?
C7 C21 C20 121.94(18) . . ?
C7 C21 C16 121.29(17) . . ?
C20 C21 C16 116.76(17) . . ?
C8 C22 H17 109.5 . . ?
C8 C22 H16 109.5 . . ?
H17 C22 H16 109.5 . . ?
C8 C22 H15 109.5 . . ?
H17 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?
C24 C23 C28 117.51(18) . . ?
C24 C23 C5 118.87(18) . . ?
C28 C23 C5 123.62(18) . . ?
C23 C24 C25 121.8(2) . . ?
C23 C24 H20 119.1 . . ?
C25 C24 H20 119.1 . . ?
C26 C25 C24 118.5(2) . . ?
C26 C25 H23 120.8 . . ?
C24 C25 H23 120.8 . . ?
C25 C26 C27 121.6(2) . . ?
C25 C26 Cl2 119.36(17) . . ?
C27 C26 Cl2 119.09(18) . . ?
C26 C27 C28 119.2(2) . . ?
C26 C27 H22 120.4 . . ?
C28 C27 H22 120.4 . . ?
C27 C28 C23 121.5(2) . . ?
C27 C28 H21 119.3 . . ?
C23 C28 H21 119.3 . . ?
C1 C29 H27 109.5 . . ?
C1 C29 H26 109.5 . . ?
H27 C29 H26 109.5 . . ?
C1 C29 H28 109.5 . . ?
H27 C29 H28 109.5 . . ?
H26 C29 H28 109.5 . . ?
C1 C30 H31 109.5 . . ?
C1 C30 H29 109.5 . . ?
H31 C30 H29 109.5 . . ?
C1 C30 H30 109.5 . . ?
H31 C30 H30 109.5 . . ?
H29 C30 H30 109.5 . . ?
C1 O1 H1 111(2) . . ?
C7 O2 C8 116.29(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
O1 C1 C2 C3 45.0(2) . . . . ?
C29 C1 C2 C3 -72.7(2) . . . . ?
C30 C1 C2 C3 166.29(17) . . . . ?
C1 C2 C3 C4 168.52(16) . . . . ?
C2 C3 C4 C17 36.2(2) . . . . ?
C2 C3 C4 C5 -89.1(2) . . . . ?
C2 C3 C4 C16 152.42(16) . . . . ?
C17 C4 C5 C23 -79.8(2) . . . . ?
C3 C4 C5 C23 42.5(2) . . . . ?
C16 C4 C5 C23 163.98(16) . . . . ?
C17 C4 C5 C6 51.7(2) . . . . ?
C3 C4 C5 C6 174.02(15) . . . . ?
C16 C4 C5 C6 -64.49(19) . . . . ?
C23 C5 C6 C7 172.42(16) . . . . ?
C4 C5 C6 C7 37.8(2) . . . . ?
C5 C6 C7 C21 -3.2(3) . . . . ?
C5 C6 C7 O2 176.56(15) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
Cl1 C10 C11 C12 -179.69(15) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C11 C12 C13 C16 177.96(18) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C16 C13 C14 C15 -177.93(17) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
Cl1 C10 C15 C14 179.78(15) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C12 C13 C16 C21 -36.1(3) . . . . ?
C14 C13 C16 C21 140.54(18) . . . . ?
C12 C13 C16 C4 91.1(2) . . . . ?
C14 C13 C16 C4 -92.3(2) . . . . ?
C17 C4 C16 C21 -63.85(19) . . . . ?
C3 C4 C16 C21 178.99(15) . . . . ?
C5 C4 C16 C21 56.78(19) . . . . ?
C17 C4 C16 C13 167.93(15) . . . . ?
C3 C4 C16 C13 50.8(2) . . . . ?
C5 C4 C16 C13 -71.43(19) . . . . ?
C3 C4 C17 O3 -107.4(2) . . . . ?
C5 C4 C17 O3 17.3(2) . . . . ?
C16 C4 C17 O3 133.28(18) . . . . ?
C3 C4 C17 C18 70.5(2) . . . . ?
C5 C4 C17 C18 -164.75(16) . . . . ?
C16 C4 C17 C18 -48.8(2) . . . . ?
O2 C8 C19 C20 -61.1(2) . . . . ?
C9 C8 C19 C20 59.1(2) . . . . ?
C22 C8 C19 C20 -175.56(17) . . . . ?
C8 C19 C20 C21 44.4(2) . . . . ?
O2 C7 C21 C20 -3.9(3) . . . . ?
C6 C7 C21 C20 175.74(19) . . . . ?
O2 C7 C21 C16 177.20(17) . . . . ?
C6 C7 C21 C16 -3.1(3) . . . . ?
C19 C20 C21 C7 -12.5(3) . . . . ?
C19 C20 C21 C16 166.40(17) . . . . ?
C13 C16 C21 C7 104.9(2) . . . . ?
C4 C16 C21 C7 -25.2(2) . . . . ?
C13 C16 C21 C20 -74.0(2) . . . . ?
C4 C16 C21 C20 155.89(16) . . . . ?
C6 C5 C23 C24 127.88(19) . . . . ?
C4 C5 C23 C24 -101.1(2) . . . . ?
C6 C5 C23 C28 -51.9(2) . . . . ?
C4 C5 C23 C28 79.1(2) . . . . ?
C28 C23 C24 C25 -1.2(3) . . . . ?
C5 C23 C24 C25 178.94(18) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C27 1.7(3) . . . . ?
C24 C25 C26 Cl2 -178.40(16) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
Cl2 C26 C27 C28 178.60(16) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C24 C23 C28 C27 1.4(3) . . . . ?
C5 C23 C28 C27 -178.73(18) . . . . ?
C21 C7 O2 C8 -13.8(3) . . . . ?
C6 C7 O2 C8 166.52(16) . . . . ?
C9 C8 O2 C7 -77.6(2) . . . . ?
C22 C8 O2 C7 164.74(16) . . . . ?
C19 C8 O2 C7 45.5(2) . . . . ?

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
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564
O1 H1 O2 0.85(3) 2.03(3) 2.869(2) 167(3) 1_655
C6 H18 O3 0.97 2.44 2.926(3) 111.0 .
C15 H4 Cl2 0.93 2.99 3.880(2) 161.3 2_666
C27 H22 Cl1 0.93 2.94 3.678(2) 137.6 1_564

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_5bc
_database_code_depnum_ccdc_archive 'CCDC 2243300'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_publcif_datablock.id            {8a2ff812-e6af-4ede-827e-fddd2a6de49a}

# publcif _publ_body_element loop end

_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            'C25 H26 O5'
_chemical_formula_weight         406.46

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   8.7057(10)
_cell_length_b                   18.724(2)
_cell_length_c                   12.0239(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1959.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9710
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.38

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            100962
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4255
_reflns_number_gt                4164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.997
_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       'Bruker APEX3'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0489P)²+0.4791P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0086(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4255
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
C1 C 0.6066(3) 0.69101(12) 0.70905(18) 0.0188(4) Uani 1 1 d . . . . .
H1A H 0.5675 0.7383 0.6919 0.023 Uiso 1 1 calc R U . . .
H1B H 0.6433 0.6913 0.7852 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6828(2) 0.67140(11) 0.52106(17) 0.0125(4) Uani 1 1 d . . . . .
C3 C 0.5569(2) 0.61382(10) 0.51040(17) 0.0120(4) Uani 1 1 d . . . . .
H3 H 0.5185 0.6143 0.4338 0.014 Uiso 1 1 calc R U . . .
C4 C 0.6272(2) 0.53991(10) 0.53334(16) 0.0110(4) Uani 1 1 d . . . . .
H4 H 0.6760 0.5416 0.6068 0.013 Uiso 1 1 calc R U . . .
C5 C 0.5153(2) 0.47800(10) 0.53327(16) 0.0113(4) Uani 1 1 d . . . . .
C6 C 0.3890(2) 0.47810(10) 0.46694(17) 0.0129(4) Uani 1 1 d . . . . .
H6 H 0.3674 0.5187 0.4252 0.015 Uiso 1 1 calc R U . . .
C7 C 0.2877(2) 0.41792(10) 0.45903(17) 0.0126(4) Uani 1 1 d . . . . .
C8 C 0.3181(2) 0.35559(11) 0.52206(16) 0.0121(4) Uani 1 1 d . . . . .
C9 C 0.2201(2) 0.29582(11) 0.50703(17) 0.0153(4) Uani 1 1 d . . . . .
H9 H 0.2400 0.2538 0.5457 0.018 Uiso 1 1 calc R U . . .
C10 C 0.0961(2) 0.29900(12) 0.43613(18) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.0330 0.2593 0.4278 0.022 Uiso 1 1 calc R U . . .
C11 C 0.4785(3) 0.63662(12) 0.69730(18) 0.0200(4) Uani 1 1 d . . . . .
H11A H 0.5135 0.5906 0.7243 0.024 Uiso 1 1 calc R U . . .
H11B H 0.3913 0.6512 0.7421 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7539(2) 0.52713(10) 0.44681(16) 0.0115(4) Uani 1 1 d . . . . .
H12 H 0.7998 0.4800 0.4595 0.014 Uiso 1 1 calc R U . . .
C13 C 0.8798(2) 0.58484(10) 0.45646(17) 0.0122(4) Uani 1 1 d . . . . .
C14 C 0.6329(2) 0.74437(11) 0.48030(18) 0.0158(4) Uani 1 1 d . . . . .
H14A H 0.7063 0.7796 0.5036 0.024 Uiso 1 1 calc R U . . .
H14B H 0.5340 0.7557 0.5109 0.024 Uiso 1 1 calc R U . . .
H14C H 0.6266 0.7440 0.4006 0.024 Uiso 1 1 calc R U . . .
C15 C 0.9848(2) 0.57217(11) 0.55516(17) 0.0152(4) Uani 1 1 d . . . . .
H15A H 1.0227 0.5241 0.5530 0.023 Uiso 1 1 calc R U . . .
H15B H 0.9285 0.5796 0.6229 0.023 Uiso 1 1 calc R U . . .
H15C H 1.0696 0.6049 0.5521 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8960(2) 0.58442(11) 0.25764(17) 0.0155(4) Uani 1 1 d . . . . .
H16A H 0.9688 0.5821 0.1967 0.019 Uiso 1 1 calc R U . . .
H16B H 0.8379 0.6284 0.2506 0.019 Uiso 1 1 calc R U . . .
C17 C 0.7887(2) 0.52137(11) 0.25234(17) 0.0149(4) Uani 1 1 d . . . . .
H17A H 0.7357 0.5207 0.1814 0.018 Uiso 1 1 calc R U . . .
H17B H 0.8463 0.4773 0.2598 0.018 Uiso 1 1 calc R U . . .
C18 C 0.5466(2) 0.41610(10) 0.60275(16) 0.0116(4) Uani 1 1 d . . . . .
C19 C 0.4474(2) 0.35563(10) 0.59879(16) 0.0116(4) Uani 1 1 d . . . . .
C20 C 0.1585(2) 0.41991(11) 0.38720(18) 0.0156(4) Uani 1 1 d . . . . .
H20 H 0.1376 0.4612 0.3469 0.019 Uiso 1 1 calc R U . . .
C21 C 0.0640(2) 0.36146(12) 0.37659(18) 0.0186(4) Uani 1 1 d . . . . .
H21 H -0.0211 0.3634 0.3299 0.022 Uiso 1 1 calc R U . . .
C22 C 0.4751(2) 0.29790(11) 0.67190(17) 0.0136(4) Uani 1 1 d . . . . .
H22 H 0.4095 0.2587 0.6706 0.016 Uiso 1 1 calc R U . . .
C23 C 0.5968(2) 0.29829(10) 0.74479(18) 0.0149(4) Uani 1 1 d . . . . .
H23 H 0.6124 0.2598 0.7923 0.018 Uiso 1 1 calc R U . . .
C24 C 0.6971(2) 0.35658(11) 0.74759(18) 0.0147(4) Uani 1 1 d . . . . .
H24 H 0.7801 0.3567 0.7963 0.018 Uiso 1 1 calc R U . . .
C25 C 0.6723(2) 0.41388(11) 0.67771(18) 0.0138(4) Uani 1 1 d . . . . .
H25 H 0.7401 0.4522 0.6798 0.017 Uiso 1 1 calc R U . . .
O1 O 0.73157(16) 0.67418(8) 0.63535(12) 0.0149(3) Uani 1 1 d . . . . .
O2 O 0.43193(16) 0.63022(8) 0.58309(13) 0.0159(3) Uani 1 1 d . . . . .
O3 O 0.81435(15) 0.65518(7) 0.45676(12) 0.0126(3) Uani 1 1 d . . . . .
O4 O 0.97694(16) 0.58383(8) 0.36193(12) 0.0139(3) Uani 1 1 d . . . . .
O5 O 0.68003(16) 0.52757(8) 0.34092(12) 0.0135(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 1.438(2) . ?
C1 C11 1.517(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O3 1.415(2) . ?
C2 O1 1.439(2) . ?
C2 C14 1.515(3) . ?
C2 C3 1.543(3) . ?
C3 O2 1.429(2) . ?
C3 C4 1.538(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.514(3) . ?
C4 C12 1.535(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.359(3) . ?
C5 C18 1.455(3) . ?
C6 C7 1.434(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.416(3) . ?
C7 C20 1.419(3) . ?
C8 C9 1.419(3) . ?
C8 C19 1.456(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C21 1.399(3) . ?
C10 H10 0.9300 . ?
C11 O2 1.437(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.426(2) . ?
C12 C13 1.543(3) . ?
C12 H12 0.9800 . ?
C13 O4 1.417(2) . ?
C13 O3 1.435(2) . ?
C13 C15 1.517(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.439(3) . ?
C16 C17 1.507(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O5 1.429(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C25 1.418(3) . ?
C18 C19 1.425(3) . ?
C19 C22 1.414(3) . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.375(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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 C11 110.60(17) . . ?
O1 C1 H1A 109.5 . . ?
C11 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C11 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O3 C2 O1 106.90(15) . . ?
O3 C2 C14 104.42(16) . . ?
O1 C2 C14 111.15(16) . . ?
O3 C2 C3 112.32(15) . . ?
O1 C2 C3 108.31(15) . . ?
C14 C2 C3 113.55(16) . . ?
O2 C3 C4 112.74(16) . . ?
O2 C3 C2 109.87(15) . . ?
C4 C3 C2 109.35(15) . . ?
O2 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C5 C4 C12 110.02(16) . . ?
C5 C4 C3 115.65(15) . . ?
C12 C4 C3 107.73(15) . . ?
C5 C4 H4 107.7 . . ?
C12 C4 H4 107.7 . . ?
C3 C4 H4 107.7 . . ?
C6 C5 C18 119.35(18) . . ?
C6 C5 C4 121.33(17) . . ?
C18 C5 C4 119.28(17) . . ?
C5 C6 C7 122.37(18) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C8 C7 C20 119.70(17) . . ?
C8 C7 C6 119.82(18) . . ?
C20 C7 C6 120.47(18) . . ?
C7 C8 C9 118.00(18) . . ?
C7 C8 C19 118.89(17) . . ?
C9 C8 C19 123.11(18) . . ?
C10 C9 C8 121.08(19) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C21 120.62(19) . . ?
C9 C10 H10 119.7 . . ?
C21 C10 H10 119.7 . . ?
O2 C11 C1 110.63(17) . . ?
O2 C11 H11A 109.5 . . ?
C1 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O5 C12 C4 106.28(15) . . ?
O5 C12 C13 112.52(15) . . ?
C4 C12 C13 110.50(16) . . ?
O5 C12 H12 109.2 . . ?
C4 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
O4 C13 O3 104.55(15) . . ?
O4 C13 C15 105.41(15) . . ?
O3 C13 C15 112.38(16) . . ?
O4 C13 C12 110.75(16) . . ?
O3 C13 C12 111.15(15) . . ?
C15 C13 C12 112.17(16) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C17 109.55(16) . . ?
O4 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
O4 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
O5 C17 C16 108.37(16) . . ?
O5 C17 H17A 110.0 . . ?
C16 C17 H17A 110.0 . . ?
O5 C17 H17B 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C25 C18 C19 117.75(17) . . ?
C25 C18 C5 122.21(17) . . ?
C19 C18 C5 120.02(17) . . ?
C22 C19 C18 118.91(17) . . ?
C22 C19 C8 121.70(17) . . ?
C18 C19 C8 119.38(17) . . ?
C21 C20 C7 120.67(19) . . ?
C21 C20 H20 119.7 . . ?
C7 C20 H20 119.7 . . ?
C20 C21 C10 119.87(19) . . ?
C20 C21 H21 120.1 . . ?
C10 C21 H21 120.1 . . ?
C23 C22 C19 121.57(19) . . ?
C23 C22 H22 119.2 . . ?
C19 C22 H22 119.2 . . ?
C22 C23 C24 120.05(19) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.63(19) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C18 122.05(18) . . ?
C24 C25 H25 119.0 . . ?
C18 C25 H25 119.0 . . ?
C1 O1 C2 111.91(15) . . ?
C3 O2 C11 112.82(15) . . ?
C2 O3 C13 121.32(15) . . ?
C13 O4 C16 113.99(14) . . ?
C12 O5 C17 111.51(14) . . ?

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
O3 C2 C3 O2 175.76(16) . . . . ?
O1 C2 C3 O2 57.94(19) . . . . ?
C14 C2 C3 O2 -66.0(2) . . . . ?
O3 C2 C3 C4 51.5(2) . . . . ?
O1 C2 C3 C4 -66.29(19) . . . . ?
C14 C2 C3 C4 169.73(17) . . . . ?
O2 C3 C4 C5 53.7(2) . . . . ?
C2 C3 C4 C5 176.23(16) . . . . ?
O2 C3 C4 C12 177.22(15) . . . . ?
C2 C3 C4 C12 -60.24(19) . . . . ?
C12 C4 C5 C6 -90.4(2) . . . . ?
C3 C4 C5 C6 31.9(3) . . . . ?
C12 C4 C5 C18 87.4(2) . . . . ?
C3 C4 C5 C18 -150.28(17) . . . . ?
C18 C5 C6 C7 -2.7(3) . . . . ?
C4 C5 C6 C7 175.13(18) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C20 -178.90(19) . . . . ?
C20 C7 C8 C9 2.6(3) . . . . ?
C6 C7 C8 C9 -176.46(18) . . . . ?
C20 C7 C8 C19 -177.44(19) . . . . ?
C6 C7 C8 C19 3.5(3) . . . . ?
C7 C8 C9 C10 -2.2(3) . . . . ?
C19 C8 C9 C10 177.8(2) . . . . ?
C8 C9 C10 C21 0.3(3) . . . . ?
O1 C1 C11 O2 -53.8(2) . . . . ?
C5 C4 C12 O5 64.94(19) . . . . ?
C3 C4 C12 O5 -61.95(18) . . . . ?
C5 C4 C12 C13 -172.70(16) . . . . ?
C3 C4 C12 C13 60.4(2) . . . . ?
O5 C12 C13 O4 -47.6(2) . . . . ?
C4 C12 C13 O4 -166.20(15) . . . . ?
O5 C12 C13 O3 68.2(2) . . . . ?
C4 C12 C13 O3 -50.4(2) . . . . ?
O5 C12 C13 C15 -165.05(16) . . . . ?
C4 C12 C13 C15 76.3(2) . . . . ?
O4 C16 C17 O5 61.2(2) . . . . ?
C6 C5 C18 C25 -176.95(19) . . . . ?
C4 C5 C18 C25 5.2(3) . . . . ?
C6 C5 C18 C19 1.6(3) . . . . ?
C4 C5 C18 C19 -176.31(17) . . . . ?
C25 C18 C19 C22 2.3(3) . . . . ?
C5 C18 C19 C22 -176.28(18) . . . . ?
C25 C18 C19 C8 -179.36(18) . . . . ?
C5 C18 C19 C8 2.1(3) . . . . ?
C7 C8 C19 C22 173.73(18) . . . . ?
C9 C8 C19 C22 -6.3(3) . . . . ?
C7 C8 C19 C18 -4.6(3) . . . . ?
C9 C8 C19 C18 175.43(18) . . . . ?
C8 C7 C20 C21 -1.2(3) . . . . ?
C6 C7 C20 C21 177.9(2) . . . . ?
C7 C20 C21 C10 -0.7(3) . . . . ?
C9 C10 C21 C20 1.2(3) . . . . ?
C18 C19 C22 C23 -1.3(3) . . . . ?
C8 C19 C22 C23 -179.58(18) . . . . ?
C19 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C18 0.4(3) . . . . ?
C19 C18 C25 C24 -1.9(3) . . . . ?
C5 C18 C25 C24 176.61(19) . . . . ?
C11 C1 O1 C2 57.9(2) . . . . ?
O3 C2 O1 C1 179.51(15) . . . . ?
C14 C2 O1 C1 66.1(2) . . . . ?
C3 C2 O1 C1 -59.26(19) . . . . ?
C4 C3 O2 C11 65.1(2) . . . . ?
C2 C3 O2 C11 -57.2(2) . . . . ?
C1 C11 O2 C3 54.9(2) . . . . ?
O1 C2 O3 C13 73.5(2) . . . . ?
C14 C2 O3 C13 -168.65(16) . . . . ?
C3 C2 O3 C13 -45.2(2) . . . . ?
O4 C13 O3 C2 163.74(15) . . . . ?
C15 C13 O3 C2 -82.4(2) . . . . ?
C12 C13 O3 C2 44.2(2) . . . . ?
O3 C13 O4 C16 -70.07(18) . . . . ?
C15 C13 O4 C16 171.28(15) . . . . ?
C12 C13 O4 C16 49.7(2) . . . . ?
C17 C16 O4 C13 -57.6(2) . . . . ?
C4 C12 O5 C17 175.69(15) . . . . ?
C13 C12 O5 C17 54.6(2) . . . . ?
C16 C17 O5 C12 -60.99(19) . . . . ?

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
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .
C14 H14B O3 0.96 2.62 3.363(2) 134.5 4_465
C15 H15B O1 0.96 2.47 3.072(3) 120.6 .

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
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