# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dbr71
_database_code_depnum_ccdc_archive 'CCDC 2292620'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.5552(4)
_cell_length_b                   7.1623(3)
_cell_length_c                   23.1013(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2242.82(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6335
_cell_measurement_temperature    298.98
_cell_measurement_theta_max      22.8100
_cell_measurement_theta_min      2.3090
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.98
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  90.00   0.50    3.00    --   16.22  30.00  30.00  200
  2  ω      1.00  63.00   0.50    3.00    --   16.22-113.00 138.00  124
  3  ω     10.00  71.00   0.50    3.00    --   16.22-125.00  90.00  122
  4  ω    -37.00  21.00   0.50    3.00    --  -15.60 -94.00   0.00  116
  5  ω    -37.00  53.00   0.50    3.00    --   16.22 -94.00   0.00  180
  6  ω    -41.00  58.00   0.50    3.00    --  -15.60  30.00 -90.00  198
  7  ω     -8.00  86.00   0.50    3.00    --   16.22  45.00-120.00  188
  8  ω    -37.00  21.00   0.50    3.00    --  -15.60 -94.00-180.00  116
  9  ω    -37.00  21.00   0.50    3.00    --  -15.60 -94.00 -90.00  116
 10  ω    -40.00  55.00   0.50    3.00    --  -15.60  45.00-180.00  190
 11  ω    -63.00  -1.00   0.50    3.00    --  -15.60 113.00-130.00  124
 12  ω    -11.00  86.00   0.50    3.00    --   16.22  61.00  60.00  194
 13  ω    -40.00  55.00   0.50    3.00    --  -15.60  45.00  90.00  190
 14  ω    -37.00  21.00   0.50    3.00    --  -15.60 -94.00  90.00  116
 15  ω    -57.00  41.00   0.50    3.00    --   16.22 -30.00  60.00  196
 16  ω    -70.00 -10.00   0.50    3.00    --  -15.60 125.00 150.00  120
 17  ω    -87.00  50.50   0.50    3.00    --  -15.60  15.00  60.00  275
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016301000
_diffrn_orient_matrix_UB_12      -0.0227761000
_diffrn_orient_matrix_UB_13      0.0298694000
_diffrn_orient_matrix_UB_21      0.0513991000
_diffrn_orient_matrix_UB_22      0.0172216000
_diffrn_orient_matrix_UB_23      0.0022232000
_diffrn_orient_matrix_UB_31      -0.0097132000
_diffrn_orient_matrix_UB_32      0.0948055000
_diffrn_orient_matrix_UB_33      0.0067619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                932
_reflns_number_total             1989
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.151
_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)+(0.0499P)²+2.6121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.2085
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70000(19) 0.2975(4) 0.44636(12) 0.0634(9) Uani 1 1 d . . . . .
O3 O 0.4564(2) 0.1989(5) 0.54496(12) 0.0656(9) Uani 1 1 d . . . . .
H3 H 0.407051 0.226595 0.526280 0.098 Uiso 1 1 calc GR . . . .
O2 O 0.79840(19) 0.1964(5) 0.51493(13) 0.0763(10) Uani 1 1 d . . . . .
C3 C 0.5373(3) 0.2323(5) 0.51297(17) 0.0525(10) Uani 1 1 d . . . . .
C4 C 0.6275(3) 0.1887(6) 0.53534(18) 0.0538(11) Uani 1 1 d . . . . .
C2 C 0.5287(3) 0.3097(6) 0.45672(17) 0.0562(11) Uani 1 1 d . . . . .
H2 H 0.466890 0.340020 0.441962 0.067 Uiso 1 1 calc R . . . .
C5 C 0.7115(3) 0.2251(6) 0.5013(2) 0.0605(12) Uani 1 1 d . . . . .
C1 C 0.6089(3) 0.3388(6) 0.42526(19) 0.0619(12) Uani 1 1 d . . . . .
C6 C 0.6401(3) 0.1039(7) 0.5941(2) 0.0742(14) Uani 1 1 d . . . . .
H6A H 0.589680 0.009326 0.599432 0.089 Uiso 1 1 calc R . . . .
H6B H 0.703645 0.041996 0.595543 0.089 Uiso 1 1 calc R . . . .
C8 C 0.6131(3) 0.4150(7) 0.3653(2) 0.0787(15) Uani 1 1 d . . . . .
H8A H 0.653811 0.526315 0.365509 0.094 Uiso 1 1 calc R . . . .
H8B H 0.547063 0.451942 0.353886 0.094 Uiso 1 1 calc R . . . .
C9 C 0.6536(4) 0.2800(9) 0.3201(2) 0.0866(17) Uani 1 1 d . . . . .
H9 H 0.722481 0.253576 0.330182 0.104 Uiso 1 1 calc R . . . .
C10 C 0.5988(4) 0.0975(9) 0.3200(2) 0.1039(19) Uani 1 1 d . . . . .
H10A H 0.606838 0.037125 0.356783 0.156 Uiso 1 1 calc GR . . . .
H10B H 0.624653 0.018625 0.289978 0.156 Uiso 1 1 calc GR . . . .
H10C H 0.530044 0.120147 0.313056 0.156 Uiso 1 1 calc GR . . . .
C7 C 0.6341(5) 0.2393(9) 0.6432(2) 0.114(2) Uani 1 1 d . . . . .
H7A H 0.687125 0.327612 0.640213 0.171 Uiso 1 1 calc GR . . . .
H7B H 0.639149 0.173093 0.679169 0.171 Uiso 1 1 calc GR . . . .
H7C H 0.572166 0.304135 0.641623 0.171 Uiso 1 1 calc GR . . . .
C11 C 0.6528(4) 0.3722(10) 0.2606(2) 0.117(2) Uani 1 1 d . . . . .
H11A H 0.586930 0.411382 0.251336 0.175 Uiso 1 1 calc GR . . . .
H11B H 0.675244 0.284517 0.232032 0.175 Uiso 1 1 calc GR . . . .
H11C H 0.695750 0.478824 0.260861 0.175 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.379(5) . ?
O1 C1 1.360(5) . ?
O3 H3 0.8200 . ?
O3 C3 1.345(4) . ?
O2 C5 1.236(4) . ?
C3 C4 1.363(5) . ?
C3 C2 1.418(5) . ?
C4 C5 1.410(5) . ?
C4 C6 1.496(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.325(5) . ?
C1 C8 1.489(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.494(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.525(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.503(7) . ?
C9 C11 1.527(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C1 O1 C5 121.0(3) . . ?
C3 O3 H3 109.5 . . ?
O3 C3 C4 118.9(4) . . ?
O3 C3 C2 120.4(3) . . ?
C4 C3 C2 120.8(4) . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 C6 122.6(4) . . ?
C5 C4 C6 119.3(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
O1 C5 C4 119.4(4) . . ?
O2 C5 O1 113.9(4) . . ?
O2 C5 C4 126.6(4) . . ?
O1 C1 C8 112.3(4) . . ?
C2 C1 O1 121.0(4) . . ?
C2 C1 C8 126.8(4) . . ?
C4 C6 H6A 108.6 . . ?
C4 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C4 114.8(4) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C1 C8 H8A 108.6 . . ?
C1 C8 H8B 108.6 . . ?
C1 C8 C9 114.7(4) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C11 109.9(5) . . ?
C10 C9 C8 112.0(4) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C11 111.7(5) . . ?
C11 C9 H9 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_dbr70
_database_code_depnum_ccdc_archive 'CCDC 2292621'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;School of Chemical Sciences, Central University of Karnataka
India
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_audit_creation_date             2023-12-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.2134(6)
_cell_length_b                   9.7698(10)
_cell_length_c                   15.9903(12)
_cell_angle_alpha                96.982(7)
_cell_angle_beta                 91.685(8)
_cell_angle_gamma                96.327(9)
_cell_volume                     802.73(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    297.6
_cell_measurement_theta_max      24.5630
_cell_measurement_theta_min      2.1050
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.044
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.113
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_unetI/netI     0.2048
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15181
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.6
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  59.00   0.50   14.95    --  -14.97  30.00 -30.00  200
  2  ω    -11.00  86.00   0.50   14.95    --   16.22  61.00-120.00  194
  3  ω    -41.00  59.00   0.50   14.95    --  -14.97  30.00-180.00  200
  4  ω    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 -90.00  118
  5  ω     26.00  90.00   0.50   14.95    --   16.22-155.00 -90.00  128
  6  ω     10.00  71.00   0.50   14.95    --   16.22-125.00  30.00  122
  7  ω      7.00  68.00   0.50   14.95    --   16.22-120.00  66.00  122
  8  ω    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 120.00  118
  9  ω    -37.00  22.00   0.50   14.95    --  -14.97 -94.00  90.00  118
 10  ω    -54.00  41.00   0.50   14.95    --   16.22 -45.00  30.00  190
 11  ω    -37.00  22.00   0.50   14.95    --  -14.97 -94.00 -60.00  118
 12  ω    -57.00  41.00   0.50   14.95    --   16.22 -30.00 -90.00  196
 13  ω    -39.00  55.00   0.50   14.95    --  -14.97  45.00 -90.00  188
 14  ω    -39.00  55.00   0.50   14.95    --  -14.97  45.00-180.00  188
 15  ω    -41.00  59.00   0.50   14.95    --  -14.97  30.00-180.00  200
 16  ω    -57.00  41.00   0.50   14.95    --   16.22 -30.00-180.00  196
 17  ω    -88.00 -26.00   0.50   14.95    --  -14.97 155.00 -51.00  124
 18  ω    -63.00  75.00   0.50   14.95    --   16.22 -15.00   0.00  276
 19  ω    -65.00  -6.00   0.50   14.95    --  -14.97 120.00 151.00  118
 20  ω    -89.00  10.00   0.50   14.95    --  -14.97 -30.00   0.00  198
 21  ω    -85.00  13.00   0.50   14.95    --  -14.97 -61.00 -60.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1010969000
_diffrn_orient_matrix_UB_12      -0.0445642000
_diffrn_orient_matrix_UB_13      0.0145882000
_diffrn_orient_matrix_UB_21      -0.0258992000
_diffrn_orient_matrix_UB_22      -0.0341092000
_diffrn_orient_matrix_UB_23      -0.0416219000
_diffrn_orient_matrix_UB_31      0.0887807000
_diffrn_orient_matrix_UB_32      -0.0476648000
_diffrn_orient_matrix_UB_33      0.0074651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                1322
_reflns_number_total             4392
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2517
_refine_ls_R_factor_gt           0.0827
_refine_ls_restrained_S_all      0.870
_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)+(0.0781P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.2148
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C20) = Uanis(C19)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C28(H28)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C27(H27A,H27B), C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B),
 C17(H17A,H17B), C4(H4A,H4B), C18(H18A,H18B), C1(H1A,H1B), C19(H19A,H19B),
 C5(H5A,H5B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C10(H10)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C6(H6A,H6B,H6C), C21(H21A,H21B,H21C)
3.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2090(17) 0.2308(11) 0.4239(8) 0.098(3) Uani 1 1 d . . . . .
O6 O 0.7904(18) 0.4804(12) 0.4498(8) 0.115(4) Uani 1 1 d . . . . .
H6 H 0.665350 0.444769 0.472492 0.172 Uiso 1 1 calc GR . . . .
O2 O -0.3556(18) 0.0973(10) 0.5767(8) 0.114(3) Uani 1 1 d . . . . .
H2 H -0.413010 0.016859 0.559824 0.171 Uiso 1 1 calc GR . . . .
O4 O 1.067(2) 0.8502(10) 0.5857(8) 0.110(3) Uani 1 1 d . . . . .
O3 O 0.3920(19) 0.3830(11) 0.5288(7) 0.121(4) Uani 1 1 d . . . . .
C26 C 0.859(3) 0.770(2) 0.6125(12) 0.100(5) Uani 1 1 d . . . . .
C24 C 0.875(3) 0.602(2) 0.4930(15) 0.104(6) Uani 1 1 d . . . . .
O5 O 1.357(2) 0.8866(11) 0.4917(8) 0.133(5) Uani 1 1 d . . . . .
C25 C 0.770(3) 0.6497(19) 0.5675(14) 0.095(5) Uani 1 1 d . . . . .
H25 H 0.631267 0.595838 0.587056 0.114 Uiso 1 1 calc R . . . .
C11 C 0.021(3) 0.1290(18) 0.3906(12) 0.104(5) Uani 1 1 d . . . . .
C10 C -0.164(3) 0.0835(16) 0.4420(12) 0.094(5) Uani 1 1 d . . . . .
H10 H -0.288228 0.010933 0.420740 0.112 Uiso 1 1 calc R . . . .
C12 C 0.049(3) 0.0832(16) 0.3006(11) 0.117(5) Uani 1 1 d . . . . .
H12A H -0.079794 0.004929 0.282650 0.140 Uiso 1 1 calc R . . . .
H12B H 0.217811 0.051546 0.293287 0.140 Uiso 1 1 calc R . . . .
C22 C 1.174(3) 0.803(3) 0.5085(14) 0.108(6) Uani 1 1 d . . . . .
C7 C 0.215(3) 0.295(2) 0.5071(13) 0.091(5) Uani 1 1 d . . . . .
C9 C -0.174(3) 0.1415(17) 0.5249(13) 0.090(5) Uani 1 1 d . . . . .
C13 C 0.020(4) 0.197(2) 0.2438(12) 0.143(7) Uani 1 1 d . . . . .
H13 H 0.161066 0.270573 0.260525 0.172 Uiso 1 1 calc R . . . .
C23 C 1.092(3) 0.675(2) 0.4635(15) 0.104(6) Uani 1 1 d . . . . .
C8 C 0.022(3) 0.2453(18) 0.5592(12) 0.088(5) Uani 1 1 d . . . . .
C27 C 0.766(3) 0.8381(18) 0.6926(13) 0.126(6) Uani 1 1 d . . . . .
H27A H 0.742090 0.933081 0.685487 0.152 Uiso 1 1 calc R . . . .
H27B H 0.598850 0.790744 0.703116 0.152 Uiso 1 1 calc R . . . .
C2 C 0.199(3) 0.2555(18) 0.7076(13) 0.122(5) Uani 1 1 d . . . . .
H2A H 0.128243 0.160474 0.711420 0.147 Uiso 1 1 calc R . . . .
H2B H 0.367243 0.252621 0.683578 0.147 Uiso 1 1 calc R . . . .
C3 C 0.235(4) 0.330(2) 0.7937(15) 0.174(8) Uani 1 1 d . . . . .
H3A H 0.068265 0.330356 0.818761 0.209 Uiso 1 1 calc R . . . .
H3B H 0.302548 0.425507 0.790233 0.209 Uiso 1 1 calc R . . . .
C16 C 1.226(3) 0.6312(17) 0.3864(13) 0.122(6) Uani 1 1 d . . . . .
H16A H 1.408862 0.660923 0.396054 0.146 Uiso 1 1 calc R . . . .
H16B H 1.203593 0.530583 0.376236 0.146 Uiso 1 1 calc R . . . .
C14 C -0.223(3) 0.262(2) 0.2523(12) 0.172(7) Uani 1 1 d . . . . .
H14A H -0.366579 0.190494 0.249344 0.258 Uiso 1 1 calc GR . . . .
H14B H -0.241387 0.317361 0.207550 0.258 Uiso 1 1 calc GR . . . .
H14C H -0.217894 0.319020 0.305642 0.258 Uiso 1 1 calc GR . . . .
C17 C 1.136(4) 0.685(2) 0.3100(14) 0.160(7) Uani 1 1 d . . . . .
H17A H 1.152820 0.785844 0.320056 0.192 Uiso 1 1 calc R . . . .
H17B H 0.954335 0.652531 0.298344 0.192 Uiso 1 1 calc R . . . .
C28 C 0.941(4) 0.839(2) 0.7675(16) 0.162(7) Uani 1 1 d . . . . .
H28 H 1.106392 0.891313 0.757192 0.194 Uiso 1 1 calc R . . . .
C4 C 0.418(4) 0.268(3) 0.8522(15) 0.187(8) Uani 1 1 d . . . . .
H4A H 0.346711 0.174764 0.859635 0.224 Uiso 1 1 calc R . . . .
H4B H 0.583874 0.263352 0.826805 0.224 Uiso 1 1 calc R . . . .
C18 C 1.290(5) 0.640(2) 0.2323(15) 0.210(10) Uani 1 1 d . . . . .
H18A H 1.473551 0.662114 0.246135 0.252 Uiso 1 1 calc R . . . .
H18B H 1.255781 0.539751 0.217686 0.252 Uiso 1 1 calc R . . . .
C1 C 0.029(3) 0.3144(16) 0.6487(12) 0.112(5) Uani 1 1 d . . . . .
H1A H 0.087358 0.412359 0.649381 0.135 Uiso 1 1 calc R . . . .
H1B H -0.145173 0.306899 0.668758 0.135 Uiso 1 1 calc R . . . .
C15 C 0.059(3) 0.142(2) 0.1526(11) 0.211(11) Uani 1 1 d . . . . .
H15A H 0.211821 0.095262 0.149568 0.317 Uiso 1 1 calc GR . . . .
H15B H 0.076305 0.217272 0.119426 0.317 Uiso 1 1 calc GR . . . .
H15C H -0.087873 0.077125 0.131279 0.317 Uiso 1 1 calc GR . . . .
C29 C 0.994(4) 0.697(2) 0.7854(13) 0.224(11) Uani 1 1 d . . . . .
H29A H 0.833373 0.642430 0.793428 0.336 Uiso 1 1 calc GR . . . .
H29B H 1.103133 0.704915 0.835455 0.336 Uiso 1 1 calc GR . . . .
H29C H 1.077614 0.652410 0.738632 0.336 Uiso 1 1 calc GR . . . .
C30 C 0.832(5) 0.915(2) 0.8453(14) 0.213(9) Uani 1 1 d . . . . .
H30A H 0.809806 1.007763 0.835711 0.319 Uiso 1 1 calc GR . . . .
H30B H 0.949850 0.917017 0.892956 0.319 Uiso 1 1 calc GR . . . .
H30C H 0.668458 0.866512 0.856372 0.319 Uiso 1 1 calc GR . . . .
C19 C 1.223(10) 0.706(6) 0.162(2) 0.433(16) Uani 1 1 d . . . . .
H19A H 1.048594 0.668720 0.142351 0.519 Uiso 1 1 calc R . . . .
H19B H 1.222031 0.803977 0.181018 0.519 Uiso 1 1 calc R . . . .
C6 C 0.617(6) 0.290(3) 0.9915(16) 0.321(18) Uani 1 1 d . . . . .
H6A H 0.641257 0.346464 1.045329 0.481 Uiso 1 1 calc GR . . . .
H6B H 0.781500 0.282073 0.967135 0.481 Uiso 1 1 calc GR . . . .
H6C H 0.535222 0.199784 0.998639 0.481 Uiso 1 1 calc GR . . . .
C5 C 0.454(5) 0.355(4) 0.9358(19) 0.284(15) Uani 1 1 d . . . . .
H5A H 0.534629 0.447263 0.929088 0.341 Uiso 1 1 calc R . . . .
H5B H 0.287789 0.364071 0.960277 0.341 Uiso 1 1 calc R . . . .
C20 C 1.371(10) 0.692(5) 0.102(2) 0.433(16) Uani 1 1 d . . . . .
H20A H 1.375466 0.593338 0.084720 0.519 Uiso 1 1 calc R . . . .
H20B H 1.544678 0.730558 0.122100 0.519 Uiso 1 1 calc R . . . .
C21 C 1.304(9) 0.755(4) 0.029(2) 0.433(16) Uani 1 1 d . . . . .
H21A H 1.438228 0.748843 -0.010487 0.649 Uiso 1 1 calc GR . . . .
H21B H 1.284551 0.851202 0.046011 0.649 Uiso 1 1 calc GR . . . .
H21C H 1.144559 0.708422 0.003428 0.649 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.363(16) . ?
O1 C7 1.397(17) . ?
O6 H6 0.8200 . ?
O6 C24 1.321(19) . ?
O2 H2 0.8200 . ?
O2 C9 1.346(15) . ?
O4 C26 1.380(17) . ?
O4 C22 1.418(19) . ?
O3 C7 1.202(18) . ?
C26 C25 1.329(19) . ?
C26 C27 1.49(2) . ?
C24 C25 1.377(19) . ?
C24 C23 1.40(2) . ?
O5 C22 1.242(19) . ?
C25 H25 0.9300 . ?
C11 C10 1.359(18) . ?
C11 C12 1.47(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.382(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.534(18) . ?
C22 C23 1.38(2) . ?
C7 C8 1.410(18) . ?
C9 C8 1.404(19) . ?
C13 H13 0.9800 . ?
C13 C14 1.477(19) . ?
C13 C15 1.519(18) . ?
C23 C16 1.48(2) . ?
C8 C1 1.50(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.48(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.473(18) . ?
C2 C1 1.484(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.53(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.471(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.55(2) . ?
C28 H28 0.9800 . ?
C28 C29 1.51(2) . ?
C28 C30 1.52(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.49(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.41(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.26(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C5 1.46(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.44(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C7 123.5(14) . . ?
C24 O6 H6 109.5 . . ?
C9 O2 H2 109.5 . . ?
C26 O4 C22 118.0(16) . . ?
O4 C26 C27 110.6(18) . . ?
C25 C26 O4 119.8(17) . . ?
C25 C26 C27 129.6(19) . . ?
O6 C24 C25 122.3(17) . . ?
O6 C24 C23 117(2) . . ?
C25 C24 C23 120.8(19) . . ?
C26 C25 C24 122.6(16) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
O1 C11 C12 113.3(15) . . ?
C10 C11 O1 118.2(17) . . ?
C10 C11 C12 128.5(18) . . ?
C11 C10 H10 118.9 . . ?
C11 C10 C9 122.1(16) . . ?
C9 C10 H10 118.9 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.7(14) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O5 C22 O4 111(2) . . ?
O5 C22 C23 126.5(19) . . ?
C23 C22 O4 122.5(19) . . ?
O1 C7 C8 117.1(18) . . ?
O3 C7 O1 117.0(16) . . ?
O3 C7 C8 126(2) . . ?
O2 C9 C10 122.8(16) . . ?
O2 C9 C8 117.7(17) . . ?
C10 C9 C8 119.4(15) . . ?
C12 C13 H13 106.6 . . ?
C14 C13 C12 115.0(16) . . ?
C14 C13 H13 106.6 . . ?
C14 C13 C15 111.4(15) . . ?
C15 C13 C12 110.0(18) . . ?
C15 C13 H13 106.6 . . ?
C24 C23 C16 125(2) . . ?
C22 C23 C24 116(2) . . ?
C22 C23 C16 118.6(17) . . ?
C7 C8 C1 117.0(17) . . ?
C9 C8 C7 119.5(18) . . ?
C9 C8 C1 123.4(16) . . ?
C26 C27 H27A 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C28 C27 C26 114.7(15) . . ?
C28 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C3 C2 C1 116.1(16) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C2 C3 C4 114.7(18) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C23 C16 H16A 108.5 . . ?
C23 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C23 114.9(16) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C16 C17 C18 112.2(19) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C27 C28 H28 107.8 . . ?
C27 C28 C29 113.7(18) . . ?
C27 C28 C30 110.4(19) . . ?
C29 C28 H28 107.8 . . ?
C29 C28 C30 109(2) . . ?
C30 C28 H28 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 111(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111(3) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C8 C1 H1A 108.7 . . ?
C8 C1 H1B 108.7 . . ?
C2 C1 C8 114.2(15) . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114(5) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 C4 109(3) . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C19 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
C19 C20 C21 116(5) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.113
_oxdiff_exptl_absorpt_empirical_full_min 0.468
####################################################################### 
# 
# 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_dbr67
_database_code_depnum_ccdc_archive 'CCDC 2292622'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H26 O3)'
_chemical_formula_sum            'C32 H52 O6'
_chemical_formula_weight         532.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1560(2)
_cell_length_b                   10.2227(2)
_cell_length_c                   17.7959(4)
_cell_angle_alpha                81.850(2)
_cell_angle_beta                 88.334(2)
_cell_angle_gamma                87.904(2)
_cell_volume                     1647.27(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11092
_cell_measurement_temperature    298.3
_cell_measurement_theta_max      22.7630
_cell_measurement_theta_min      2.1550
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.954
_diffrn_reflns_theta_min         2.014
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.3
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  22.00   0.50    6.00    --  -14.97 -94.00   0.00  118
  2  ω    -37.00  53.00   0.50    6.00    --   16.22 -94.00  90.00  180
  3  ω    -37.00  53.00   0.50    6.00    --   16.22 -94.00 120.00  180
  4  ω    -43.00  20.00   0.50    6.00    --  -14.97 -91.00 173.00  126
  5  ω    -57.00  41.00   0.50    6.00    --   16.22 -30.00 -90.00  196
  6  ω    -37.00  22.00   0.50    6.00    --  -14.97 -94.00-150.00  118
  7  ω    -57.00  41.00   0.50    6.00    --   16.22 -30.00-180.00  196
  8  ω    -54.00  41.00   0.50    6.00    --   16.22 -45.00-180.00  190
  9  ω    -51.00  45.00   0.50    6.00    --  -14.97  91.00 -72.00  192
 10  ω    -19.00  44.00   0.50    6.00    --   16.22  91.00 -72.00  126
 11  ω    -63.00  75.00   0.50    6.00    --   16.22 -15.00 -90.00  276
 12  ω    -69.00 -10.00   0.50    6.00    --  -14.97 125.00-150.00  118
 13  ω    -69.00 -10.00   0.50    6.00    --  -14.97 125.00 -60.00  118
 14  ω    -69.00 -10.00   0.50    6.00    --  -14.97 125.00 -30.00  118
 15  ω    -31.00  -2.00   0.50    6.00    --   16.22 114.00  67.51   58
 16  ω    -39.00  55.00   0.50    6.00    --  -14.97  45.00  90.00  188
 17  ω    -44.00  52.00   0.50    6.00    --   16.22 -91.00 173.00  192
 18  ω    -57.00  41.00   0.50    6.00    --   16.22 -30.00 120.00  196
 19  ω    -88.00  16.00   0.50    6.00    --  -14.97 -77.00  60.00  208
 20  ω    -89.00  10.00   0.50    6.00    --  -14.97 -30.00 150.00  198
 21  ω    -89.00 -26.50   0.50    6.00    --  -14.97 -30.00 -90.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0457366000
_diffrn_orient_matrix_UB_12      0.0455818000
_diffrn_orient_matrix_UB_13      -0.0223840000
_diffrn_orient_matrix_UB_21      0.0064016000
_diffrn_orient_matrix_UB_22      -0.0426618000
_diffrn_orient_matrix_UB_23      -0.0281574000
_diffrn_orient_matrix_UB_31      -0.0622898000
_diffrn_orient_matrix_UB_32      0.0319468000
_diffrn_orient_matrix_UB_33      -0.0181182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3313
_reflns_number_total             6897
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0884
_refine_ls_restrained_S_all      1.051
_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)+(0.1528P)²+0.3783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2591
_refine_ls_wR_factor_ref         0.3129
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C13)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C2(H2A,H2B), C1(H1A,H1B), C18(H18A,H18B), C20(H20A,H20B),
 C19(H19A,H19B), C4(H4A,H4B), C3(H3A,H3B), C21(H21A,H21B), C5(H5A,H5B),
 C22(H22A,H22B), C6(H6A,H6B), C23(H23A,H23B), C7(H7A,H7B), C24(H24A,H24B),
 C8(H8A,H8B), C15(H15A,H15B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C11(H11)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C32(H29,H32A,H32B)
3.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.3031(2) 0.44090(19) 0.42274(12) 0.0677(6) Uani 1 1 d . . . . .
O002 O 0.8029(2) -0.0841(2) 0.56731(14) 0.0769(7) Uani 1 1 d . . . . .
O003 O 0.5676(2) 0.1909(2) 0.42973(12) 0.0767(7) Uani 1 1 d . . . . .
H003 H 0.525759 0.241886 0.455517 0.115 Uiso 1 1 calc GR . . . .
O004 O 0.0745(2) 0.6676(2) 0.55787(12) 0.0786(7) Uani 1 1 d . . . . .
H004 H 0.026901 0.724836 0.531225 0.118 Uiso 1 1 calc GR . . . .
O005 O 0.9102(3) -0.1604(2) 0.46971(15) 0.0951(8) Uani 1 1 d . . . . .
O006 O 0.4136(3) 0.3287(3) 0.52000(15) 0.1152(10) Uani 1 1 d . . . . .
C26 C 0.2108(3) 0.5385(3) 0.39083(17) 0.0600(8) Uani 1 1 d . . . . .
C27 C 0.1362(3) 0.6155(3) 0.43428(17) 0.0579(7) Uani 1 1 d . . . . .
H27 H 0.074224 0.683299 0.412170 0.070 Uiso 1 1 calc R . . . .
C11 C 0.6375(3) 0.0967(3) 0.55449(18) 0.0618(8) Uani 1 1 d . . . . .
H11 H 0.578843 0.158428 0.575986 0.074 Uiso 1 1 calc R . . . .
C12 C 0.6473(3) 0.1009(3) 0.47460(18) 0.0598(8) Uani 1 1 d . . . . .
C13 C 0.7362(4) 0.0137(3) 0.4416(2) 0.0757(7) Uani 1 1 d . . . . .
C10 C 0.7127(3) 0.0041(3) 0.59820(19) 0.0693(9) Uani 1 1 d . . . . .
C28 C 0.1518(3) 0.5937(3) 0.51374(18) 0.0611(8) Uani 1 1 d . . . . .
C14 C 0.8204(3) -0.0795(3) 0.4903(2) 0.0708(9) Uani 1 1 d . . . . .
C30 C 0.3231(4) 0.4177(3) 0.49969(19) 0.0779(10) Uani 1 1 d . . . . .
C17 C 0.2089(4) 0.5478(3) 0.30695(19) 0.0792(10) Uani 1 1 d . . . . .
H17A H 0.304898 0.572910 0.286578 0.095 Uiso 1 1 calc R . . . .
H17B H 0.139755 0.617874 0.287782 0.095 Uiso 1 1 calc R . . . .
C29 C 0.2423(4) 0.4959(4) 0.54547(19) 0.0898(12) Uani 1 1 d . . . . .
C2 C 0.6534(5) 0.0876(3) 0.7232(2) 0.0876(11) Uani 1 1 d . . . . .
H2A H 0.552731 0.108663 0.709294 0.105 Uiso 1 1 calc R . . . .
H2B H 0.709887 0.164872 0.705446 0.105 Uiso 1 1 calc R . . . .
C1 C 0.7089(5) -0.0235(4) 0.6830(2) 0.0965(12) Uani 1 1 d . . . . .
H1A H 0.648112 -0.098874 0.698374 0.116 Uiso 1 1 calc R . . . .
H1B H 0.807107 -0.048552 0.699799 0.116 Uiso 1 1 calc R . . . .
C18 C 0.1694(5) 0.4233(3) 0.27755(19) 0.0892(11) Uani 1 1 d . . . . .
H18A H 0.076179 0.394314 0.299969 0.107 Uiso 1 1 calc R . . . .
H18B H 0.242533 0.354364 0.292909 0.107 Uiso 1 1 calc R . . . .
C20 C 0.1307(6) 0.3248(4) 0.1569(2) 0.1143(15) Uani 1 1 d . . . . .
H20A H 0.037946 0.290253 0.176811 0.137 Uiso 1 1 calc R . . . .
H20B H 0.206096 0.257904 0.171983 0.137 Uiso 1 1 calc R . . . .
C19 C 0.1594(5) 0.4432(4) 0.1917(2) 0.1038(13) Uani 1 1 d . . . . .
H19A H 0.082432 0.508932 0.177418 0.125 Uiso 1 1 calc R . . . .
H19B H 0.250539 0.479117 0.170216 0.125 Uiso 1 1 calc R . . . .
C4 C 0.6161(6) 0.1722(4) 0.8492(2) 0.1195(16) Uani 1 1 d . . . . .
H4A H 0.515384 0.197810 0.837358 0.143 Uiso 1 1 calc R . . . .
H4B H 0.675539 0.246780 0.829766 0.143 Uiso 1 1 calc R . . . .
C3 C 0.6599(6) 0.0608(4) 0.8079(2) 0.1095(14) Uani 1 1 d . . . . .
H3A H 0.597535 -0.012537 0.825584 0.131 Uiso 1 1 calc R . . . .
H3B H 0.759209 0.032614 0.821337 0.131 Uiso 1 1 calc R . . . .
C21 C 0.1259(6) 0.3480(5) 0.0711(2) 0.1274(17) Uani 1 1 d . . . . .
H21A H 0.044167 0.408437 0.056647 0.153 Uiso 1 1 calc R . . . .
H21B H 0.214358 0.391891 0.051876 0.153 Uiso 1 1 calc R . . . .
C5 C 0.6282(7) 0.1482(5) 0.9333(3) 0.1332(18) Uani 1 1 d . . . . .
H5A H 0.559523 0.080956 0.952964 0.160 Uiso 1 1 calc R . . . .
H5B H 0.725493 0.111606 0.944862 0.160 Uiso 1 1 calc R . . . .
C22 C 0.1125(7) 0.2317(5) 0.0332(3) 0.1341(18) Uani 1 1 d . . . . .
H22A H 0.022057 0.189686 0.050763 0.161 Uiso 1 1 calc R . . . .
H22B H 0.192132 0.169647 0.049058 0.161 Uiso 1 1 calc R . . . .
C6 C 0.6025(7) 0.2606(5) 0.9747(3) 0.1414(19) Uani 1 1 d . . . . .
H6A H 0.504434 0.295892 0.963711 0.170 Uiso 1 1 calc R . . . .
H6B H 0.669655 0.328437 0.954018 0.170 Uiso 1 1 calc R . . . .
C23 C 0.1136(8) 0.2556(5) -0.0522(3) 0.149(2) Uani 1 1 d . . . . .
H23A H 0.030647 0.313851 -0.067824 0.179 Uiso 1 1 calc R . . . .
H23B H 0.201218 0.302706 -0.069431 0.179 Uiso 1 1 calc R . . . .
C7 C 0.6169(8) 0.2392(6) 1.0583(3) 0.162(2) Uani 1 1 d . . . . .
H7A H 0.546276 0.174548 1.079229 0.195 Uiso 1 1 calc R . . . .
H7B H 0.713232 0.199877 1.069427 0.195 Uiso 1 1 calc R . . . .
C24 C 0.1086(10) 0.1408(7) -0.0919(4) 0.202(3) Uani 1 1 d . . . . .
H24A H 0.191425 0.082351 -0.076244 0.242 Uiso 1 1 calc R . . . .
H24B H 0.020816 0.093852 -0.074933 0.242 Uiso 1 1 calc R . . . .
C8 C 0.5979(10) 0.3519(8) 1.0988(4) 0.214(4) Uani 1 1 d . . . . .
H8A H 0.666824 0.417213 1.076733 0.257 Uiso 1 1 calc R . . . .
H8B H 0.500712 0.389868 1.088234 0.257 Uiso 1 1 calc R . . . .
C25 C 0.1103(11) 0.1642(8) -0.1722(4) 0.236(4) Uani 1 1 d . . . . .
H25A H 0.038508 0.232151 -0.188879 0.354 Uiso 1 1 calc GR . . . .
H25B H 0.088003 0.084397 -0.191494 0.354 Uiso 1 1 calc GR . . . .
H25C H 0.205345 0.192031 -0.190608 0.354 Uiso 1 1 calc GR . . . .
C9 C 0.6136(11) 0.3354(10) 1.1767(5) 0.285(6) Uani 1 1 d . . . . .
H9A H 0.548984 0.268789 1.200164 0.428 Uiso 1 1 calc GR . . . .
H9B H 0.589839 0.417385 1.195352 0.428 Uiso 1 1 calc GR . . . .
H9C H 0.712730 0.308496 1.188648 0.428 Uiso 1 1 calc GR . . . .
C16 C 0.8640(6) 0.0979(6) 0.3218(3) 0.154(2) Uani 1 1 d . . . . .
H16A H 0.870312 0.091608 0.268486 0.231 Uiso 1 1 calc GR . . . .
H16B H 0.955821 0.070161 0.344536 0.231 Uiso 1 1 calc GR . . . .
H16C H 0.841142 0.187864 0.328856 0.231 Uiso 1 1 calc GR . . . .
C15 C 0.7487(4) 0.0126(3) 0.35775(19) 0.0757(7) Uani 1 1 d . . . . .
H15A H 0.769334 -0.077221 0.347909 0.091 Uiso 1 1 calc R . . . .
H15B H 0.655900 0.042006 0.335119 0.091 Uiso 1 1 calc R . . . .
C31 C 0.2350(6) 0.4184(7) 0.6480(4) 0.183(3) Uani 1 1 d . . . . .
H31A H 0.150572 0.444702 0.677207 0.220 Uiso 1 1 calc R . . . .
H31B H 0.254348 0.323562 0.656694 0.220 Uiso 1 1 calc R . . . .
C32 C 0.3392(9) 0.4837(7) 0.6496(5) 0.213(4) Uani 1 1 d . . . . .
H29 H 0.357987 0.531324 0.599961 0.319 Uiso 1 1 calc GR . . . .
H32A H 0.422425 0.427444 0.664911 0.319 Uiso 1 1 calc GR . . . .
H32B H 0.321411 0.545270 0.685123 0.319 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C26 1.356(3) . ?
O001 C30 1.373(4) . ?
O002 C10 1.363(3) . ?
O002 C14 1.369(4) . ?
O003 H003 0.8200 . ?
O003 C12 1.339(3) . ?
O004 H004 0.8200 . ?
O004 C28 1.336(3) . ?
O005 C14 1.230(3) . ?
O006 C30 1.230(4) . ?
C26 C27 1.336(4) . ?
C26 C17 1.483(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.411(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.417(4) . ?
C11 C10 1.322(4) . ?
C12 C13 1.368(4) . ?
C13 C14 1.416(4) . ?
C13 C15 1.494(5) . ?
C10 C1 1.495(5) . ?
C28 C29 1.345(4) . ?
C30 C29 1.399(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.503(5) . ?
C29 C31 1.885(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.492(5) . ?
C2 C3 1.496(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.518(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.470(5) . ?
C20 C21 1.513(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.479(6) . ?
C4 C5 1.488(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.459(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.459(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.505(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.482(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.456(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.445(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.415(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.384(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C15 1.468(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.188(7) . ?
C32 H29 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 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
C26 O001 C30 121.7(2) . . ?
C10 O002 C14 121.5(2) . . ?
C12 O003 H003 109.5 . . ?
C28 O004 H004 109.5 . . ?
O001 C26 C17 112.6(2) . . ?
C27 C26 O001 120.2(3) . . ?
C27 C26 C17 127.2(3) . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.9(3) . . ?
C28 C27 H27 120.1 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(3) . . ?
O003 C12 C11 120.0(2) . . ?
O003 C12 C13 118.6(3) . . ?
C13 C12 C11 121.4(3) . . ?
C12 C13 C14 117.4(3) . . ?
C12 C13 C15 123.5(3) . . ?
C14 C13 C15 119.1(3) . . ?
O002 C10 C1 111.4(3) . . ?
C11 C10 O002 120.9(3) . . ?
C11 C10 C1 127.6(3) . . ?
O004 C28 C27 120.4(2) . . ?
O004 C28 C29 119.8(3) . . ?
C29 C28 C27 119.9(3) . . ?
O002 C14 C13 119.4(3) . . ?
O005 C14 O002 115.1(3) . . ?
O005 C14 C13 125.5(3) . . ?
O001 C30 C29 118.1(3) . . ?
O006 C30 O001 114.3(3) . . ?
O006 C30 C29 127.6(3) . . ?
C26 C17 H17A 108.5 . . ?
C26 C17 H17B 108.5 . . ?
C26 C17 C18 115.1(3) . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C28 C29 C30 120.1(3) . . ?
C28 C29 C31 125.4(3) . . ?
C30 C29 C31 112.2(3) . . ?
H2A C2 H2B 107.5 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.8(3) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C10 C1 H1A 108.3 . . ?
C10 C1 H1B 108.3 . . ?
C2 C1 C10 115.8(3) . . ?
C2 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C17 C18 C19 112.0(3) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H20A C20 H20B 107.6 . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C19 C20 C21 114.5(4) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C18 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
C20 C19 C18 116.2(3) . . ?
C20 C19 H19A 108.2 . . ?
C20 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
H4A C4 H4B 107.3 . . ?
C3 C4 H4A 108.1 . . ?
C3 C4 H4B 108.1 . . ?
C3 C4 C5 116.6(4) . . ?
C5 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C2 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C4 C3 C2 116.2(4) . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C20 C21 H21A 108.1 . . ?
C20 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C22 C21 C20 116.8(4) . . ?
C22 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C4 C5 H5A 107.9 . . ?
C4 C5 H5B 107.9 . . ?
H5A C5 H5B 107.2 . . ?
C6 C5 C4 117.8(5) . . ?
C6 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
C21 C22 H22A 108.2 . . ?
C21 C22 H22B 108.2 . . ?
C21 C22 C23 116.2(5) . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C5 C6 H6A 107.7 . . ?
C5 C6 H6B 107.7 . . ?
C5 C6 C7 118.6(5) . . ?
H6A C6 H6B 107.1 . . ?
C7 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
C22 C23 H23A 107.9 . . ?
C22 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C24 C23 C22 117.6(6) . . ?
C24 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C6 C7 H7A 107.7 . . ?
C6 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?
C8 C7 C6 118.4(6) . . ?
C8 C7 H7A 107.7 . . ?
C8 C7 H7B 107.7 . . ?
C23 C24 H24A 108.0 . . ?
C23 C24 H24B 108.0 . . ?
H24A C24 H24B 107.2 . . ?
C25 C24 C23 117.2(7) . . ?
C25 C24 H24A 108.0 . . ?
C25 C24 H24B 108.0 . . ?
C7 C8 H8A 107.4 . . ?
C7 C8 H8B 107.4 . . ?
H8A C8 H8B 106.9 . . ?
C9 C8 C7 119.7(8) . . ?
C9 C8 H8A 107.4 . . ?
C9 C8 H8B 107.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C13 C15 H15A 109.1 . . ?
C13 C15 H15B 109.1 . . ?
C16 C15 C13 112.5(3) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C29 C31 H31A 115.1 . . ?
C29 C31 H31B 115.1 . . ?
H31A C31 H31B 112.2 . . ?
C32 C31 C29 81.0(7) . . ?
C32 C31 H31A 115.1 . . ?
C32 C31 H31B 115.1 . . ?
C31 C32 H29 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H29 C32 H32A 109.5 . . ?
H29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.505
