# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_4881
_database_code_depnum_ccdc_archive 'CCDC 1574014'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;
_audit_creation_date             2017-04-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 O3'
_chemical_formula_sum            'C23 H20 O3'
_chemical_formula_weight         344.39
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2479(5)
_cell_length_b                   10.4410(5)
_cell_length_c                   9.4838(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.490(5)
_cell_angle_gamma                90
_cell_volume                     903.20(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    109.1
_cell_measurement_theta_max      71.0850
_cell_measurement_theta_min      4.2308
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5793
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.224
_diffrn_reflns_theta_min         4.727
_diffrn_ambient_temperature      109.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega   12.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -105.0000  109.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -10.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -105.0000  -70.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  132.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   59.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   91.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 17 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 20 omega  101.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
 21 omega   99.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 23 omega   73.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
 24 omega   63.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000  -59.0000 48

#__ type_ start__ end____ width___ exp.time_
 25 omega   61.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  109.0000 35

#__ type_ start__ end____ width___ exp.time_
 26 omega   81.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000   -1.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0752920000
_diffrn_orient_matrix_UB_12      0.1315583000
_diffrn_orient_matrix_UB_13      -0.0240955000
_diffrn_orient_matrix_UB_21      -0.1373589000
_diffrn_orient_matrix_UB_22      -0.0546370000
_diffrn_orient_matrix_UB_23      0.0508159000
_diffrn_orient_matrix_UB_31      0.0627567000
_diffrn_orient_matrix_UB_32      0.0384710000
_diffrn_orient_matrix_UB_33      0.1549146000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3340
_reflns_number_total             3387
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.068
_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)+(0.0490P)²+0.1197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_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
O1 O -0.26872(16) -0.30169(13) -0.52026(15) 0.0249(3) Uani 1 1 d . . . . .
O3 O -0.28367(15) -0.44022(15) -1.09324(15) 0.0242(3) Uani 1 1 d . . . . .
O2 O -0.10577(16) -0.32921(17) -1.17425(15) 0.0275(3) Uani 1 1 d . . . . .
C22 C -0.16284(19) -0.36716(19) -1.0772(2) 0.0179(4) Uani 1 1 d . . . . .
C2 C -0.10903(19) -0.33798(18) -0.9250(2) 0.0165(4) Uani 1 1 d . . . . .
C18 C -0.1942(2) 0.3156(2) -0.6552(2) 0.0254(5) Uani 1 1 d . . . . .
H18 H -0.1351 0.3649 -0.7043 0.030 Uiso 1 1 calc R U . . .
C20 C -0.3884(2) 0.3005(2) -0.5174(2) 0.0248(5) Uani 1 1 d . . . . .
H20 H -0.4615 0.3392 -0.4758 0.030 Uiso 1 1 calc R U . . .
C7 C -0.1628(2) -0.11394(18) -0.61233(19) 0.0162(4) Uani 1 1 d . . . . .
C4 C -0.0863(2) -0.32787(18) -0.67469(19) 0.0167(4) Uani 1 1 d . . . . .
H4 H -0.0346 -0.3980 -0.6190 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4171(2) -0.4883(2) -0.9202(3) 0.0336(5) Uani 1 1 d . . . . .
H12 H 0.5002 -0.5358 -0.9289 0.040 Uiso 1 1 calc R U . . .
C19 C -0.3018(2) 0.37397(19) -0.5910(2) 0.0256(5) Uani 1 1 d . . . . .
H19 H -0.3154 0.4621 -0.5978 0.031 Uiso 1 1 calc R U . . .
C21 C -0.3671(2) 0.1691(2) -0.5050(2) 0.0212(4) Uani 1 1 d . . . . .
H21 H -0.4248 0.1207 -0.4535 0.025 Uiso 1 1 calc R U . . .
C3 C -0.1716(2) -0.37403(17) -0.81463(19) 0.0167(4) Uani 1 1 d . . . . .
H3 H -0.2575 -0.4218 -0.8229 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2785(2) -0.2928(2) -0.9580(2) 0.0284(5) Uani 1 1 d . . . . .
H14 H 0.2703 -0.2091 -0.9917 0.034 Uiso 1 1 calc R U . . .
C8 C -0.1839(2) -0.25338(19) -0.58928(19) 0.0177(4) Uani 1 1 d . . . . .
C17 C -0.1744(2) 0.18368(19) -0.6461(2) 0.0215(4) Uani 1 1 d . . . . .
H17 H -0.1039 0.1451 -0.6916 0.026 Uiso 1 1 calc R U . . .
C15 C -0.2452(2) -0.03051(18) -0.5543(2) 0.0181(4) Uani 1 1 d . . . . .
H15 H -0.3036 -0.0669 -0.4940 0.022 Uiso 1 1 calc R U . . .
C1 C 0.0326(2) -0.26501(19) -0.8803(2) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.0320 -0.1868 -0.9376 0.021 Uiso 1 1 calc R U . . .
C5 C 0.0212(2) -0.22955(17) -0.72295(19) 0.0162(4) Uani 1 1 d . . . . .
H5 H 0.1174 -0.2340 -0.6618 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1819(2) -0.4709(2) -0.8447(2) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.1079 -0.5079 -0.8028 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3070(2) -0.5411(2) -0.8565(3) 0.0294(5) Uani 1 1 d . . . . .
H11 H 0.3168 -0.6243 -0.8212 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0513(2) -0.09620(19) -0.7104(2) 0.0184(4) Uani 1 1 d . . . . .
H6A H 0.0218 -0.0337 -0.6709 0.022 Uiso 1 1 calc R U . . .
H6B H -0.0987 -0.0667 -0.8036 0.022 Uiso 1 1 calc R U . . .
C23 C -0.3468(2) -0.4713(3) -1.2388(2) 0.0329(5) Uani 1 1 d . . . . .
H23A H -0.4420 -0.5086 -1.2406 0.049 Uiso 1 1 calc R U . . .
H23B H -0.2846 -0.5313 -1.2769 0.049 Uiso 1 1 calc R U . . .
H23C H -0.3558 -0.3948 -1.2957 0.049 Uiso 1 1 calc R U . . .
C9 C 0.1666(2) -0.34534(19) -0.8953(2) 0.0191(4) Uani 1 1 d . . . . .
C16 C -0.2593(2) 0.10853(19) -0.5695(2) 0.0181(4) Uani 1 1 d . . . . .
C13 C 0.4024(3) -0.3641(3) -0.9710(3) 0.0373(6) Uani 1 1 d . . . . .
H13 H 0.4761 -0.3279 -1.0141 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.212(2) . ?
O3 C22 1.341(2) . ?
O3 C23 1.445(2) . ?
O2 C22 1.202(2) . ?
C22 C2 1.478(3) . ?
C2 C3 1.331(3) . ?
C2 C1 1.514(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C18 C17 1.390(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(3) . ?
C20 C21 1.388(3) . ?
C7 C8 1.490(3) . ?
C7 C15 1.335(3) . ?
C7 C6 1.509(3) . ?
C4 H4 0.9800 . ?
C4 C3 1.507(3) . ?
C4 C8 1.522(3) . ?
C4 C5 1.550(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(3) . ?
C12 C13 1.382(4) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C21 C16 1.403(3) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C14 C9 1.388(3) . ?
C14 C13 1.389(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.463(3) . ?
C1 H1 0.9800 . ?
C1 C5 1.558(2) . ?
C1 C9 1.522(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.559(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C10 C9 1.396(3) . ?
C11 H11 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C13 H13 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
C22 O3 C23 115.77(16) . . ?
O3 C22 C2 111.62(16) . . ?
O2 C22 O3 124.31(18) . . ?
O2 C22 C2 124.07(18) . . ?
C22 C2 C1 120.89(16) . . ?
C3 C2 C22 126.10(17) . . ?
C3 C2 C1 112.97(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.48(19) . . ?
C21 C20 H20 119.8 . . ?
C8 C7 C6 109.25(16) . . ?
C15 C7 C8 118.67(17) . . ?
C15 C7 C6 131.95(18) . . ?
C3 C4 H4 112.0 . . ?
C3 C4 C8 111.21(15) . . ?
C3 C4 C5 102.71(14) . . ?
C8 C4 H4 112.0 . . ?
C8 C4 C5 106.52(15) . . ?
C5 C4 H4 112.0 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.65(19) . . ?
C20 C19 H19 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C16 120.60(19) . . ?
C16 C21 H21 119.7 . . ?
C2 C3 C4 111.69(16) . . ?
C2 C3 H3 124.2 . . ?
C4 C3 H3 124.2 . . ?
C9 C14 H14 119.6 . . ?
C9 C14 C13 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
O1 C8 C7 126.75(18) . . ?
O1 C8 C4 124.64(18) . . ?
C7 C8 C4 108.53(15) . . ?
C18 C17 H17 119.7 . . ?
C18 C17 C16 120.64(19) . . ?
C16 C17 H17 119.7 . . ?
C7 C15 H15 114.6 . . ?
C7 C15 C16 130.90(18) . . ?
C16 C15 H15 114.6 . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C5 101.29(14) . . ?
C2 C1 C9 112.12(16) . . ?
C5 C1 H1 109.7 . . ?
C9 C1 H1 109.7 . . ?
C9 C1 C5 113.90(15) . . ?
C4 C5 C1 105.88(15) . . ?
C4 C5 H5 111.0 . . ?
C4 C5 C6 105.29(14) . . ?
C1 C5 H5 111.0 . . ?
C1 C5 C6 112.56(15) . . ?
C6 C5 H5 111.0 . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.41(19) . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C7 C6 C5 106.49(15) . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C9 C1 119.87(19) . . ?
C14 C9 C10 118.53(18) . . ?
C10 C9 C1 121.58(17) . . ?
C21 C16 C15 117.52(18) . . ?
C17 C16 C21 118.35(18) . . ?
C17 C16 C15 124.12(18) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

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 C22 C2 C3 -2.1(3) . . . . ?
O3 C22 C2 C1 175.42(16) . . . . ?
O2 C22 C2 C3 177.4(2) . . . . ?
O2 C22 C2 C1 -5.1(3) . . . . ?
C22 C2 C3 C4 179.69(17) . . . . ?
C22 C2 C1 C5 166.51(15) . . . . ?
C22 C2 C1 C9 -71.7(2) . . . . ?
C2 C1 C5 C4 22.48(18) . . . . ?
C2 C1 C5 C6 -92.04(17) . . . . ?
C2 C1 C9 C14 134.45(19) . . . . ?
C2 C1 C9 C10 -46.9(2) . . . . ?
C18 C17 C16 C21 1.5(3) . . . . ?
C18 C17 C16 C15 -179.78(19) . . . . ?
C20 C21 C16 C17 0.0(3) . . . . ?
C20 C21 C16 C15 -178.79(19) . . . . ?
C7 C15 C16 C21 173.9(2) . . . . ?
C7 C15 C16 C17 -4.9(3) . . . . ?
C4 C5 C6 C7 18.95(19) . . . . ?
C19 C18 C17 C16 -1.8(3) . . . . ?
C19 C20 C21 C16 -1.3(3) . . . . ?
C21 C20 C19 C18 1.0(3) . . . . ?
C3 C2 C1 C5 -15.7(2) . . . . ?
C3 C2 C1 C9 106.13(19) . . . . ?
C3 C4 C8 O1 78.4(2) . . . . ?
C3 C4 C8 C7 -98.50(18) . . . . ?
C3 C4 C5 C1 -21.76(18) . . . . ?
C3 C4 C5 C6 97.66(16) . . . . ?
C8 C7 C15 C16 -173.31(19) . . . . ?
C8 C7 C6 C5 -11.6(2) . . . . ?
C8 C4 C3 C2 126.33(17) . . . . ?
C8 C4 C5 C1 -138.74(15) . . . . ?
C8 C4 C5 C6 -19.32(19) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C15 C7 C8 O1 -1.0(3) . . . . ?
C15 C7 C8 C4 175.77(17) . . . . ?
C15 C7 C6 C5 172.6(2) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C1 C5 C6 C7 133.82(16) . . . . ?
C5 C4 C3 C2 12.7(2) . . . . ?
C5 C4 C8 O1 -170.46(18) . . . . ?
C5 C4 C8 C7 12.68(19) . . . . ?
C5 C1 C9 C14 -111.3(2) . . . . ?
C5 C1 C9 C10 67.4(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C11 C10 C9 C14 0.3(3) . . . . ?
C11 C10 C9 C1 -178.4(2) . . . . ?
C6 C7 C8 O1 -177.42(18) . . . . ?
C6 C7 C8 C4 -0.6(2) . . . . ?
C6 C7 C15 C16 2.1(4) . . . . ?
C23 O3 C22 O2 -1.0(3) . . . . ?
C23 O3 C22 C2 178.53(18) . . . . ?
C9 C14 C13 C12 -0.6(4) . . . . ?
C9 C1 C5 C4 -98.08(18) . . . . ?
C9 C1 C5 C6 147.40(16) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C13 C12 C11 C10 0.7(4) . . . . ?
C13 C14 C9 C1 179.2(2) . . . . ?
C13 C14 C9 C10 0.4(3) . . . . ?

_shelx_estimated_absorpt_T_max   0.801
_shelx_estimated_absorpt_T_min   0.755
_shelx_SHELXL_version_number     2014/7
_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.
;
####################################################################### 
# 
# 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_sa5238
_database_code_depnum_ccdc_archive 'CCDC 1582747'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_chemical_absolute_configuration unk
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.139(4)
_cell_length_b                   10.409(4)
_cell_length_c                   9.569(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.930(6)
_cell_angle_gamma                90
_cell_volume                     896.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4809
_cell_measurement_theta_min      1.9565
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.213
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11029
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         3.388
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3783
_reflns_number_total             3934
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1445 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.091
_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)+(0.0260P)²+0.1881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0926
_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:
 C1(H1), C4(H4), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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
C1 C 0.6202(3) 0.6679(2) 0.5273(2) 0.0246(5) Uani 1 1 d . . . . .
H1 H 0.555623 0.589881 0.520915 0.030 Uiso 1 1 calc R . . . .
C2 C 0.5888(2) 0.7419(3) 0.3893(2) 0.0247(5) Uani 1 1 d . . . . .
C3 C 0.7135(3) 0.7747(2) 0.3427(3) 0.0246(5) Uani 1 1 d . . . . .
H3 H 0.716011 0.819281 0.256472 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8496(2) 0.7322(3) 0.4442(2) 0.0258(5) Uani 1 1 d . . . . .
H4 H 0.892253 0.804566 0.506918 0.031 Uiso 1 1 calc R . . . .
C5 C 0.9700(3) 0.6638(2) 0.3804(3) 0.0265(5) Uani 1 1 d . . . . .
H5 H 1.061145 0.658951 0.454904 0.032 Uiso 1 1 calc R . . . .
C6 C 0.9120(3) 0.5285(2) 0.3506(3) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.7993(3) 0.5014(2) 0.4459(3) 0.0270(5) Uani 1 1 d . . . . .
H7A H 0.833634 0.429979 0.511776 0.032 Uiso 1 1 calc R . . . .
H7B H 0.702354 0.477598 0.388609 0.032 Uiso 1 1 calc R . . . .
C8 C 0.7847(3) 0.6273(2) 0.5301(3) 0.0253(5) Uani 1 1 d . . . . .
H8 H 0.840707 0.621684 0.629377 0.030 Uiso 1 1 calc R . . . .
C9 C 0.6025(2) 0.7463(3) 0.6583(2) 0.0257(5) Uani 1 1 d . . . . .
C10 C 0.5664(3) 0.6824(3) 0.7752(3) 0.0323(6) Uani 1 1 d . . . . .
H10 H 0.546376 0.592777 0.769514 0.039 Uiso 1 1 calc R . . . .
C11 C 0.5594(3) 0.7480(3) 0.9006(3) 0.0381(6) Uani 1 1 d . . . . .
H11 H 0.535058 0.702966 0.979929 0.046 Uiso 1 1 calc R . . . .
C12 C 0.5876(3) 0.8785(3) 0.9101(3) 0.0365(6) Uani 1 1 d . . . . .
H12 H 0.582579 0.923586 0.995462 0.044 Uiso 1 1 calc R . . . .
C13 C 0.6232(3) 0.9426(3) 0.7940(3) 0.0359(6) Uani 1 1 d . . . . .
H13 H 0.642913 1.032260 0.799777 0.043 Uiso 1 1 calc R . . . .
C14 C 0.6305(3) 0.8770(3) 0.6689(3) 0.0311(6) Uani 1 1 d . . . . .
H14 H 0.654888 0.922222 0.589883 0.037 Uiso 1 1 calc R . . . .
C15 C 0.4362(3) 0.7724(2) 0.3199(3) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.2858(3) 0.8638(3) 0.1183(3) 0.0416(7) Uani 1 1 d . . . . .
H16A H 0.295214 0.913298 0.033160 0.062 Uiso 1 1 calc GR . . . .
H16B H 0.226950 0.912746 0.176330 0.062 Uiso 1 1 calc GR . . . .
H16C H 0.236385 0.781937 0.090459 0.062 Uiso 1 1 calc GR . . . .
C17 C 0.9628(3) 0.4534(2) 0.2562(3) 0.0260(5) Uani 1 1 d . . . . .
H17 H 1.029640 0.494793 0.205063 0.031 Uiso 1 1 calc R . . . .
C18 C 0.9333(3) 0.3179(3) 0.2177(2) 0.0263(5) Uani 1 1 d . . . . .
C19 C 1.0186(3) 0.2614(3) 0.1256(3) 0.0303(6) Uani 1 1 d . . . . .
H19 H 1.088877 0.312338 0.088093 0.036 Uiso 1 1 calc R . . . .
C20 C 1.0025(3) 0.1327(3) 0.0880(3) 0.0358(6) Uani 1 1 d . . . . .
H20 H 1.060689 0.096745 0.024566 0.043 Uiso 1 1 calc R . . . .
C21 C 0.9020(3) 0.0571(3) 0.1429(3) 0.0405(7) Uani 1 1 d . . . . .
H21 H 0.892336 -0.031492 0.119363 0.049 Uiso 1 1 calc R . . . .
C22 C 0.8155(3) 0.1116(3) 0.2324(3) 0.0408(7) Uani 1 1 d . . . . .
H22 H 0.745634 0.060015 0.269679 0.049 Uiso 1 1 calc R . . . .
C23 C 0.8298(3) 0.2410(3) 0.2684(3) 0.0332(6) Uani 1 1 d . . . . .
H23 H 0.767958 0.277249 0.328435 0.040 Uiso 1 1 calc R . . . .
O1 O 0.43200(18) 0.83947(19) 0.19946(18) 0.0331(4) Uani 1 1 d . . . . .
O2 O 0.32561(18) 0.7385(2) 0.36353(19) 0.0362(4) Uani 1 1 d . . . . .
O3 O 1.00746(19) 0.72905(19) 0.2617(2) 0.0348(4) Uani 1 1 d . . . . .
H3A H 1.098545 0.746571 0.277072 0.052 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
C1 H1 1.0000 . ?
C1 C2 1.513(3) . ?
C1 C8 1.557(3) . ?
C1 C9 1.527(3) . ?
C2 C3 1.338(3) . ?
C2 C15 1.472(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.506(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.523(3) . ?
C4 C8 1.545(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.514(4) . ?
C5 O3 1.416(3) . ?
C6 C7 1.516(3) . ?
C6 C17 1.336(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.556(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.389(4) . ?
C9 C14 1.385(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(4) . ?
C14 H14 0.9500 . ?
C15 O1 1.342(3) . ?
C15 O2 1.210(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O1 1.447(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.471(4) . ?
C18 C19 1.402(3) . ?
C18 C23 1.389(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C23 H23 0.9500 . ?
O3 H3A 0.8400 . ?

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 H1 109.8 . . ?
C2 C1 C8 100.99(18) . . ?
C2 C1 C9 114.4(2) . . ?
C8 C1 H1 109.8 . . ?
C9 C1 H1 109.8 . . ?
C9 C1 C8 111.7(2) . . ?
C3 C2 C1 112.1(2) . . ?
C3 C2 C15 126.2(2) . . ?
C15 C2 C1 121.7(2) . . ?
C2 C3 H3 124.3 . . ?
C2 C3 C4 111.5(2) . . ?
C4 C3 H3 124.3 . . ?
C3 C4 H4 111.0 . . ?
C3 C4 C5 116.9(2) . . ?
C3 C4 C8 101.61(18) . . ?
C5 C4 H4 111.0 . . ?
C5 C4 C8 104.7(2) . . ?
C8 C4 H4 111.0 . . ?
C4 C5 H5 108.0 . . ?
C6 C5 C4 104.9(2) . . ?
C6 C5 H5 108.0 . . ?
O3 C5 C4 112.9(2) . . ?
O3 C5 H5 108.0 . . ?
O3 C5 C6 114.8(2) . . ?
C5 C6 C7 108.1(2) . . ?
C17 C6 C5 121.4(2) . . ?
C17 C6 C7 130.5(2) . . ?
C6 C7 H7A 110.4 . . ?
C6 C7 H7B 110.4 . . ?
C6 C7 C8 106.4(2) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C1 C8 H8 111.5 . . ?
C4 C8 C1 104.89(19) . . ?
C4 C8 C7 104.14(19) . . ?
C4 C8 H8 111.5 . . ?
C7 C8 C1 112.9(2) . . ?
C7 C8 H8 111.5 . . ?
C10 C9 C1 118.6(2) . . ?
C14 C9 C1 122.7(2) . . ?
C14 C9 C10 118.5(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.7(3) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O1 C15 C2 112.6(2) . . ?
O2 C15 C2 124.3(2) . . ?
O2 C15 O1 123.1(2) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
C6 C17 H17 114.3 . . ?
C6 C17 C18 131.4(2) . . ?
C18 C17 H17 114.3 . . ?
C19 C18 C17 117.5(2) . . ?
C23 C18 C17 124.8(2) . . ?
C23 C18 C19 117.7(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 C22 120.7(3) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C15 O1 C16 116.03(19) . . ?
C5 O3 H3A 109.5 . . ?

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
O3 H3A O2 0.84 2.10 2.905(3) 160.5 1_655

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 -1.9(3) . . . . ?
C1 C2 C15 O1 179.4(2) . . . . ?
C1 C2 C15 O2 -2.3(4) . . . . ?
C1 C9 C10 C11 175.4(2) . . . . ?
C1 C9 C14 C13 -175.3(2) . . . . ?
C2 C1 C8 C4 27.6(2) . . . . ?
C2 C1 C8 C7 -85.1(2) . . . . ?
C2 C1 C9 C10 153.1(2) . . . . ?
C2 C1 C9 C14 -31.3(3) . . . . ?
C2 C3 C4 C5 132.8(2) . . . . ?
C2 C3 C4 C8 19.6(3) . . . . ?
C2 C15 O1 C16 174.9(2) . . . . ?
C3 C2 C15 O1 0.0(4) . . . . ?
C3 C2 C15 O2 178.2(3) . . . . ?
C3 C4 C5 C6 -77.5(3) . . . . ?
C3 C4 C5 O3 48.2(3) . . . . ?
C3 C4 C8 C1 -28.8(2) . . . . ?
C3 C4 C8 C7 90.0(2) . . . . ?
C4 C5 C6 C7 -22.8(3) . . . . ?
C4 C5 C6 C17 158.7(2) . . . . ?
C5 C4 C8 C1 -150.86(19) . . . . ?
C5 C4 C8 C7 -32.1(2) . . . . ?
C5 C6 C7 C8 2.7(3) . . . . ?
C5 C6 C17 C18 174.5(2) . . . . ?
C6 C7 C8 C1 131.3(2) . . . . ?
C6 C7 C8 C4 18.1(2) . . . . ?
C6 C17 C18 C19 -172.3(2) . . . . ?
C6 C17 C18 C23 6.1(4) . . . . ?
C7 C6 C17 C18 -3.6(5) . . . . ?
C8 C1 C2 C3 -16.5(3) . . . . ?
C8 C1 C2 C15 164.0(2) . . . . ?
C8 C1 C9 C10 -92.9(3) . . . . ?
C8 C1 C9 C14 82.6(3) . . . . ?
C8 C4 C5 C6 34.0(2) . . . . ?
C8 C4 C5 O3 159.70(19) . . . . ?
C9 C1 C2 C3 103.6(2) . . . . ?
C9 C1 C2 C15 -75.9(3) . . . . ?
C9 C1 C8 C4 -94.4(2) . . . . ?
C9 C1 C8 C7 152.8(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C15 C2 C3 C4 177.6(2) . . . . ?
C17 C6 C7 C8 -179.0(2) . . . . ?
C17 C18 C19 C20 177.4(2) . . . . ?
C17 C18 C23 C22 -176.3(2) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C18 C23 C22 2.1(4) . . . . ?
C19 C20 C21 C22 1.6(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C18 -1.3(4) . . . . ?
C23 C18 C19 C20 -1.1(4) . . . . ?
O2 C15 O1 C16 -3.4(4) . . . . ?
O3 C5 C6 C7 -147.3(2) . . . . ?
O3 C5 C6 C17 34.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
