# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_bc111173
_database_code_depnum_ccdc_archive 'CCDC 1057787'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H22 O'
_chemical_formula_sum            'C22 H22 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         302.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.8889(10)
_cell_length_b                   5.8024(3)
_cell_length_c                   15.1560(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.856(5)
_cell_angle_gamma                90.00
_cell_volume                     1652.44(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1577
_cell_measurement_theta_min      3.9370
_cell_measurement_theta_max      28.9520
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7756
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         29.43
_reflns_number_total             3864
_reflns_number_gt                2668
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.3550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3864
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.30987(6) 0.43295(19) 0.16865(7) 0.0371(3) Uani 1 1 d . . .
C1 C 0.25067(9) 0.4488(3) 0.30230(11) 0.0360(4) Uani 1 1 d . . .
H1A H 0.2594 0.4730 0.3658 0.043 Uiso 1 1 calc R . .
H1B H 0.2238 0.3070 0.2925 0.043 Uiso 1 1 calc R . .
C2 C 0.32154(8) 0.4249(3) 0.26340(11) 0.0335(4) Uani 1 1 d . . .
H2A H 0.3409 0.2725 0.2800 0.040 Uiso 1 1 calc R . .
C3 C 0.37612(8) 0.6021(3) 0.29801(11) 0.0335(4) Uani 1 1 d . . .
C4 C 0.41226(9) 0.5756(3) 0.38217(12) 0.0438(5) Uani 1 1 d . . .
H4A H 0.4019 0.4505 0.4170 0.053 Uiso 1 1 calc R . .
C5 C 0.46332(10) 0.7329(4) 0.41450(13) 0.0524(5) Uani 1 1 d . . .
H5A H 0.4869 0.7146 0.4710 0.063 Uiso 1 1 calc R . .
C6 C 0.47925(10) 0.9173(4) 0.36260(14) 0.0529(5) Uani 1 1 d . . .
H6A H 0.5141 1.0224 0.3839 0.063 Uiso 1 1 calc R . .
C7 C 0.44368(9) 0.9464(3) 0.27917(13) 0.0440(5) Uani 1 1 d . . .
H7A H 0.4547 1.0714 0.2447 0.053 Uiso 1 1 calc R . .
C8 C 0.39137(8) 0.7906(3) 0.24598(11) 0.0342(4) Uani 1 1 d . . .
C9 C 0.35286(9) 0.8198(3) 0.15451(11) 0.0384(4) Uani 1 1 d . . .
H9A H 0.3855 0.7874 0.1106 0.046 Uiso 1 1 calc R . .
H9B H 0.3373 0.9785 0.1468 0.046 Uiso 1 1 calc R . .
C10 C 0.28826(9) 0.6602(3) 0.13891(11) 0.0347(4) Uani 1 1 d . . .
C11 C 0.22721(9) 0.7429(3) 0.18745(11) 0.0347(4) Uani 1 1 d . . .
H11A H 0.2015 0.8697 0.1645 0.042 Uiso 1 1 calc R . .
C12 C 0.20754(8) 0.6463(3) 0.26120(10) 0.0306(4) Uani 1 1 d . . .
C13 C 0.14246(8) 0.7157(3) 0.30222(10) 0.0330(4) Uani 1 1 d . . .
C14 C 0.10623(9) 0.9208(3) 0.28084(12) 0.0404(4) Uani 1 1 d . . .
H14A H 0.1246 1.0232 0.2418 0.049 Uiso 1 1 calc R . .
C15 C 0.04382(10) 0.9760(4) 0.31609(13) 0.0456(5) Uani 1 1 d . . .
H15A H 0.0217 1.1158 0.3010 0.055 Uiso 1 1 calc R . .
C16 C 0.01342(10) 0.8292(4) 0.37309(12) 0.0466(5) Uani 1 1 d . . .
C17 C 0.04964(11) 0.6269(4) 0.39587(13) 0.0555(6) Uani 1 1 d . . .
H17A H 0.0311 0.5255 0.4351 0.067 Uiso 1 1 calc R . .
C18 C 0.11287(10) 0.5716(4) 0.36177(12) 0.0474(5) Uani 1 1 d . . .
H18A H 0.1360 0.4350 0.3792 0.057 Uiso 1 1 calc R . .
C19 C -0.05709(11) 0.8841(5) 0.40706(15) 0.0662(7) Uani 1 1 d . . .
H19A H -0.0737 1.0310 0.3844 0.099 Uiso 1 1 calc R . .
H19B H -0.0512 0.8889 0.4707 0.099 Uiso 1 1 calc R . .
H19C H -0.0911 0.7671 0.3877 0.099 Uiso 1 1 calc R . .
C20 C 0.26365(10) 0.6410(4) 0.04052(12) 0.0455(5) Uani 1 1 d . . .
H20A H 0.2482 0.7869 0.0123 0.055 Uiso 1 1 calc R . .
C21 C 0.29857(12) 0.4792(4) -0.01820(14) 0.0611(6) Uani 1 1 d . . .
H21A H 0.3360 0.3803 0.0090 0.073 Uiso 1 1 calc R . .
H21B H 0.3052 0.5309 -0.0777 0.073 Uiso 1 1 calc R . .
C22 C 0.22426(11) 0.4342(4) 0.00294(13) 0.0591(6) Uani 1 1 d . . .
H22A H 0.1859 0.4588 -0.0437 0.071 Uiso 1 1 calc R . .
H22B H 0.2168 0.3082 0.0430 0.071 Uiso 1 1 calc R . .


_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
O C2 1.4313(19) . ?
O C10 1.439(2) . ?
C1 C2 1.523(2) . ?
C1 C12 1.504(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.511(2) . ?
C2 H2A 0.9800 . ?
C3 C4 1.393(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.395(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.508(2) . ?
C9 C10 1.531(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(2) . ?
C10 C20 1.520(2) . ?
C11 C12 1.336(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.488(2) . ?
C13 C18 1.389(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.381(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.384(3) . ?
C16 C19 1.510(3) . ?
C17 C18 1.387(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.494(3) . ?
C20 C21 1.493(3) . ?
C20 H20A 0.9800 . ?
C21 C22 1.494(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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 O C10 110.71(11) . . ?
C2 C1 C12 111.67(14) . . ?
C2 C1 H1A 109.3 . . ?
C12 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C12 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
O C2 C1 109.52(13) . . ?
O C2 C3 110.84(13) . . ?
C1 C2 C3 113.53(14) . . ?
O C2 H2A 107.6 . . ?
C1 C2 H2A 107.6 . . ?
C3 C2 H2A 107.6 . . ?
C4 C3 C8 119.60(16) . . ?
C4 C3 C2 119.74(16) . . ?
C8 C3 C2 120.65(15) . . ?
C5 C4 C3 120.75(18) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C6 C5 C4 119.70(18) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 120.21(18) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C6 C7 C8 120.79(18) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C7 C8 C3 118.92(16) . . ?
C7 C8 C9 121.10(16) . . ?
C3 C8 C9 119.96(15) . . ?
C8 C9 C10 112.10(14) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O C10 C11 110.20(14) . . ?
O C10 C20 106.77(14) . . ?
C11 C10 C20 109.23(14) . . ?
O C10 C9 108.04(13) . . ?
C11 C10 C9 111.68(14) . . ?
C20 C10 C9 110.79(14) . . ?
C12 C11 C10 124.49(16) . . ?
C12 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
C11 C12 C13 123.22(15) . . ?
C11 C12 C1 118.74(15) . . ?
C13 C12 C1 117.95(14) . . ?
C18 C13 C14 116.38(16) . . ?
C18 C13 C12 120.85(16) . . ?
C14 C13 C12 122.71(16) . . ?
C15 C14 C13 121.74(18) . . ?
C15 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C14 C15 C16 121.70(18) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C15 C16 C17 116.94(17) . . ?
C15 C16 C19 121.4(2) . . ?
C17 C16 C19 121.6(2) . . ?
C18 C17 C16 121.73(19) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C13 121.46(18) . . ?
C17 C18 H18A 119.3 . . ?
C13 C18 H18A 119.3 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 60.05(14) . . ?
C22 C20 C10 121.57(17) . . ?
C21 C20 C10 121.43(17) . . ?
C22 C20 H20A 114.4 . . ?
C21 C20 H20A 114.4 . . ?
C10 C20 H20A 114.4 . . ?
C20 C21 C22 60.01(14) . . ?
C20 C21 H21A 117.8 . . ?
C22 C21 H21A 117.8 . . ?
C20 C21 H21B 117.8 . . ?
C22 C21 H21B 117.8 . . ?
H21A C21 H21B 114.9 . . ?
C20 C22 C21 59.94(13) . . ?
C20 C22 H22A 117.8 . . ?
C21 C22 H22A 117.8 . . ?
C20 C22 H22B 117.8 . . ?
C21 C22 H22B 117.8 . . ?
H22A C22 H22B 114.9 . . ?

_diffrn_measured_fraction_theta_max 0.846
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_jaya0902
_database_code_depnum_ccdc_archive 'CCDC 1057788'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         368.41

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8013(3)
_cell_length_b                   11.3046(7)
_cell_length_c                   15.3699(10)
_cell_angle_alpha                110.966(3)
_cell_angle_beta                 92.458(3)
_cell_angle_gamma                102.961(2)
_cell_volume                     908.83(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9457
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      26.42
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27213
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         26.44
_reflns_number_total             3687
_reflns_number_gt                2882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.3600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3687
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.11816(19) 0.67061(11) 0.16572(8) 0.0378(3) Uani 1 1 d . . .
O2 O 0.2221(3) 0.90526(15) -0.12045(11) 0.0620(4) Uani 1 1 d . . .
O3 O 0.4921(3) 0.77779(17) -0.14309(10) 0.0638(4) Uani 1 1 d . . .
C1 C -0.0909(3) 0.78112(16) 0.13896(12) 0.0351(4) Uani 1 1 d . . .
H1A H -0.2492 0.7807 0.1137 0.042 Uiso 1 1 calc R . .
C2 C 0.0002(3) 0.90677(17) 0.22544(12) 0.0382(4) Uani 1 1 d . . .
H2A H 0.0440 0.9805 0.2059 0.046 Uiso 1 1 calc R . .
H2B H -0.1263 0.9200 0.2643 0.046 Uiso 1 1 calc R . .
C3 C 0.2133(3) 0.90177(16) 0.28231(11) 0.0336(4) Uani 1 1 d . . .
C4 C 0.2630(3) 0.78644(15) 0.26457(11) 0.0332(4) Uani 1 1 d . . .
H4A H 0.4002 0.7855 0.2976 0.040 Uiso 1 1 calc R . .
C5 C 0.1111(3) 0.65672(15) 0.19423(12) 0.0333(4) Uani 1 1 d . . .
C6 C 0.2319(3) 0.61005(16) 0.10580(12) 0.0352(4) Uani 1 1 d . . .
H6A H 0.3967 0.6145 0.1241 0.042 Uiso 1 1 calc R . .
H6B H 0.1519 0.5193 0.0681 0.042 Uiso 1 1 calc R . .
C7 C 0.2246(3) 0.69235(15) 0.04769(11) 0.0334(4) Uani 1 1 d . . .
C8 C 0.0670(3) 0.77152(15) 0.06212(11) 0.0332(4) Uani 1 1 d . . .
C9 C 0.0510(3) 0.84609(17) 0.00711(12) 0.0393(4) Uani 1 1 d . . .
H9A H -0.0586 0.8966 0.0151 0.047 Uiso 1 1 calc R . .
C10 C 0.2033(3) 0.84135(18) -0.05864(13) 0.0424(4) Uani 1 1 d . . .
C11 C 0.4230(4) 0.8775(2) -0.16608(16) 0.0604(6) Uani 1 1 d . . .
H11A H 0.5540 0.9560 -0.1454 0.072 Uiso 1 1 calc R . .
H11B H 0.3822 0.8481 -0.2336 0.072 Uiso 1 1 calc R . .
C12 C 0.3620(3) 0.76444(18) -0.07269(12) 0.0428(4) Uani 1 1 d . . .
C13 C 0.3744(3) 0.68749(17) -0.02259(12) 0.0405(4) Uani 1 1 d . . .
H13A H 0.4785 0.6335 -0.0344 0.049 Uiso 1 1 calc R . .
C14 C 0.3543(3) 1.02621(16) 0.35726(11) 0.0365(4) Uani 1 1 d . . .
C15 C 0.2697(4) 1.13787(19) 0.38350(15) 0.0543(5) Uani 1 1 d . . .
H15A H 0.1257 1.1349 0.3527 0.065 Uiso 1 1 calc R . .
C16 C 0.3951(5) 1.2535(2) 0.45452(17) 0.0685(7) Uani 1 1 d . . .
H16A H 0.3348 1.3270 0.4704 0.082 Uiso 1 1 calc R . .
C17 C 0.6056(5) 1.2610(2) 0.50144(16) 0.0624(6) Uani 1 1 d . . .
H17A H 0.6877 1.3386 0.5498 0.075 Uiso 1 1 calc R . .
C18 C 0.6953(4) 1.1524(2) 0.47638(14) 0.0557(5) Uani 1 1 d . . .
H18A H 0.8404 1.1571 0.5073 0.067 Uiso 1 1 calc R . .
C19 C 0.5712(3) 1.03580(19) 0.40529(13) 0.0448(4) Uani 1 1 d . . .
H19A H 0.6336 0.9630 0.3895 0.054 Uiso 1 1 calc R . .
C20 C 0.0606(3) 0.55970(16) 0.24295(12) 0.0357(4) Uani 1 1 d . . .
C21 C -0.1210(3) 0.56219(19) 0.29918(15) 0.0474(5) Uani 1 1 d . . .
H21A H -0.2153 0.6202 0.3041 0.057 Uiso 1 1 calc R . .
C22 C -0.1630(4) 0.4792(2) 0.34797(15) 0.0538(5) Uani 1 1 d . . .
H22A H -0.2862 0.4813 0.3848 0.065 Uiso 1 1 calc R . .
C23 C -0.0236(4) 0.39394(19) 0.34216(15) 0.0525(5) Uani 1 1 d . . .
H23A H -0.0507 0.3390 0.3755 0.063 Uiso 1 1 calc R . .
C24 C 0.1562(4) 0.3904(2) 0.28673(16) 0.0562(5) Uani 1 1 d . . .
H24A H 0.2503 0.3324 0.2823 0.067 Uiso 1 1 calc R . .
C25 C 0.1982(4) 0.47242(18) 0.23741(14) 0.0474(5) Uani 1 1 d . . .
H25A H 0.3204 0.4689 0.2001 0.057 Uiso 1 1 calc R . .


_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 C1 1.4281(19) . ?
O1 C5 1.4416(19) . ?
O2 C10 1.379(2) . ?
O2 C11 1.423(3) . ?
O3 C12 1.378(2) . ?
O3 C11 1.426(3) . ?
C1 C8 1.514(2) . ?
C1 C2 1.522(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.507(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.333(2) . ?
C3 C14 1.489(2) . ?
C4 C5 1.516(2) . ?
C4 H4A 0.9300 . ?
C5 C20 1.520(2) . ?
C5 C6 1.533(2) . ?
C6 C7 1.508(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.389(2) . ?
C7 C13 1.409(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.365(2) . ?
C9 H9A 0.9300 . ?
C10 C12 1.375(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.363(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.361(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.388(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.390(2) . ?
C20 C25 1.385(2) . ?
C21 C22 1.385(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.382(3) . ?
C24 H24A 0.9300 . ?
C25 H25A 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
C1 O1 C5 110.83(11) . . ?
C10 O2 C11 105.11(15) . . ?
C12 O3 C11 105.38(16) . . ?
O1 C1 C8 111.10(13) . . ?
O1 C1 C2 109.57(13) . . ?
C8 C1 C2 112.78(13) . . ?
O1 C1 H1A 107.7 . . ?
C8 C1 H1A 107.7 . . ?
C2 C1 H1A 107.7 . . ?
C3 C2 C1 111.51(13) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C14 123.43(15) . . ?
C4 C3 C2 118.63(15) . . ?
C14 C3 C2 117.92(14) . . ?
C3 C4 C5 124.51(15) . . ?
C3 C4 H4A 117.7 . . ?
C5 C4 H4A 117.7 . . ?
O1 C5 C4 110.39(13) . . ?
O1 C5 C20 106.01(12) . . ?
C4 C5 C20 108.39(13) . . ?
O1 C5 C6 107.69(13) . . ?
C4 C5 C6 110.53(13) . . ?
C20 C5 C6 113.74(13) . . ?
C7 C6 C5 111.58(13) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C13 119.71(16) . . ?
C8 C7 C6 120.10(15) . . ?
C13 C7 C6 120.18(15) . . ?
C7 C8 C9 121.34(16) . . ?
C7 C8 C1 120.62(15) . . ?
C9 C8 C1 118.03(15) . . ?
C10 C9 C8 117.20(16) . . ?
C10 C9 H9A 121.4 . . ?
C8 C9 H9A 121.4 . . ?
C9 C10 C12 121.85(17) . . ?
C9 C10 O2 128.02(17) . . ?
C12 C10 O2 110.11(16) . . ?
O2 C11 O3 108.58(16) . . ?
O2 C11 H11A 110.0 . . ?
O3 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
O3 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 C10 121.99(17) . . ?
C13 C12 O3 128.33(18) . . ?
C10 C12 O3 109.67(17) . . ?
C12 C13 C7 117.85(16) . . ?
C12 C13 H13A 121.1 . . ?
C7 C13 H13A 121.1 . . ?
C15 C14 C19 117.14(17) . . ?
C15 C14 C3 120.47(17) . . ?
C19 C14 C3 122.37(16) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C14 120.94(19) . . ?
C18 C19 H19A 119.5 . . ?
C14 C19 H19A 119.5 . . ?
C21 C20 C25 118.15(16) . . ?
C21 C20 C5 119.61(15) . . ?
C25 C20 C5 122.15(16) . . ?
C20 C21 C22 120.75(18) . . ?
C20 C21 H21A 119.6 . . ?
C22 C21 H21A 119.6 . . ?
C23 C22 C21 120.29(19) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C24 C23 C22 119.53(18) . . ?
C24 C23 H23A 120.2 . . ?
C22 C23 H23A 120.2 . . ?
C23 C24 C25 120.47(19) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C24 C25 C20 120.81(18) . . ?
C24 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053


####################################################################### 
# 
# 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_p088a
_database_code_depnum_ccdc_archive 'CCDC 1057789'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H20 O'
_chemical_formula_sum            'C20 H20 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         276.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.2076(8)
_cell_length_b                   15.3283(17)
_cell_length_c                   16.201(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.237(13)
_cell_angle_gamma                90.00
_cell_volume                     1535.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    857
_cell_measurement_theta_min      3.5300
_cell_measurement_theta_max      23.4130
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6862
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.1076
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         29.14
_reflns_number_total             3527
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0939P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3527
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2531
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.0856(4) 0.14690(13) 0.39015(14) 0.0530(7) Uani 1 1 d . . .
C1 C 0.0446(5) 0.22996(19) 0.34716(19) 0.0400(8) Uani 1 1 d . . .
C2 C 0.1372(5) 0.3016(2) 0.40487(19) 0.0438(8) Uani 1 1 d . . .
H2A H 0.2940 0.2992 0.4084 0.053 Uiso 1 1 calc R . .
H2B H 0.0925 0.3580 0.3820 0.053 Uiso 1 1 calc R . .
C3 C 0.0640(5) 0.2930(2) 0.4900(2) 0.0517(9) Uani 1 1 d . . .
C4 C -0.0334(6) 0.2172(2) 0.5106(2) 0.0613(10) Uani 1 1 d . . .
H4A H -0.0731 0.2098 0.5641 0.074 Uiso 1 1 calc R . .
C5 C -0.0780(6) 0.1444(2) 0.4471(2) 0.0603(10) Uani 1 1 d . . .
H5A H -0.0861 0.0872 0.4736 0.072 Uiso 1 1 calc R . .
C6 C -0.2826(6) 0.1658(3) 0.3932(2) 0.0730(12) Uani 1 1 d . . .
H6A H -0.3932 0.1889 0.4258 0.088 Uiso 1 1 calc R . .
H6B H -0.3390 0.1150 0.3628 0.088 Uiso 1 1 calc R . .
C7 C -0.2033(5) 0.2353(2) 0.3346(2) 0.0513(9) Uani 1 1 d . . .
H7A H -0.2549 0.2228 0.2775 0.062 Uiso 1 1 calc R . .
H7B H -0.2532 0.2929 0.3490 0.062 Uiso 1 1 calc R . .
C8 C 0.1540(5) 0.2231(2) 0.2663(2) 0.0496(9) Uani 1 1 d . . .
H8A H 0.0878 0.1753 0.2338 0.059 Uiso 1 1 calc R . .
H8B H 0.3050 0.2084 0.2798 0.059 Uiso 1 1 calc R . .
C9 C 0.1420(5) 0.3043(2) 0.21308(19) 0.0456(8) Uani 1 1 d . . .
C10 C -0.0297(6) 0.3189(3) 0.1540(2) 0.0639(11) Uani 1 1 d . . .
H10A H -0.1409 0.2782 0.1468 0.077 Uiso 1 1 calc R . .
C11 C -0.0383(7) 0.3933(3) 0.1055(2) 0.0750(12) Uani 1 1 d . . .
H11A H -0.1553 0.4020 0.0663 0.090 Uiso 1 1 calc R . .
C12 C 0.1240(7) 0.4548(2) 0.1145(2) 0.0619(11) Uani 1 1 d . . .
H12A H 0.1161 0.5051 0.0822 0.074 Uiso 1 1 calc R . .
C13 C 0.2971(6) 0.4409(2) 0.1717(2) 0.0583(10) Uani 1 1 d . . .
H13A H 0.4084 0.4816 0.1780 0.070 Uiso 1 1 calc R . .
C14 C 0.3069(6) 0.3665(2) 0.2201(2) 0.0542(9) Uani 1 1 d . . .
H14A H 0.4262 0.3577 0.2582 0.065 Uiso 1 1 calc R . .
C15 C 0.1111(6) 0.3643(2) 0.5514(2) 0.0480(9) Uani 1 1 d . . .
C16 C 0.2993(7) 0.4135(3) 0.5537(2) 0.0682(11) Uani 1 1 d . . .
H16A H 0.3952 0.4043 0.5137 0.082 Uiso 1 1 calc R . .
C17 C 0.3469(7) 0.4759(3) 0.6141(3) 0.0783(13) Uani 1 1 d . . .
H17A H 0.4770 0.5062 0.6155 0.094 Uiso 1 1 calc R . .
C18 C 0.2052(7) 0.4936(3) 0.6718(2) 0.0680(11) Uani 1 1 d . . .
H18A H 0.2355 0.5371 0.7111 0.082 Uiso 1 1 calc R . .
C19 C 0.0167(7) 0.4459(2) 0.6707(2) 0.0692(12) Uani 1 1 d . . .
H19A H -0.0793 0.4563 0.7104 0.083 Uiso 1 1 calc R . .
C20 C -0.0300(6) 0.3831(3) 0.6111(2) 0.0629(11) Uani 1 1 d . . .
H20A H -0.1593 0.3524 0.6106 0.075 Uiso 1 1 calc R . .


_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
O C5 1.434(4) . ?
O C1 1.462(3) . ?
C1 C2 1.521(4) . ?
C1 C8 1.534(4) . ?
C1 C7 1.536(4) . ?
C2 C3 1.496(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.366(4) . ?
C3 C15 1.490(4) . ?
C4 C5 1.525(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.510(5) . ?
C5 H5A 0.9800 . ?
C6 C7 1.538(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.512(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.384(5) . ?
C9 C14 1.396(4) . ?
C10 C11 1.383(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.377(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.381(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.388(5) . ?
C15 C20 1.392(4) . ?
C16 C17 1.380(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(5) . ?
C19 H19A 0.9300 . ?
C20 H20A 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
C5 O C1 103.1(2) . . ?
O C1 C2 107.2(2) . . ?
O C1 C8 106.0(2) . . ?
C2 C1 C8 113.8(2) . . ?
O C1 C7 103.8(2) . . ?
C2 C1 C7 111.1(3) . . ?
C8 C1 C7 114.0(3) . . ?
C3 C2 C1 111.9(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C15 121.7(3) . . ?
C4 C3 C2 118.6(3) . . ?
C15 C3 C2 119.6(3) . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
O C5 C6 103.3(3) . . ?
O C5 C4 108.6(3) . . ?
C6 C5 C4 108.8(3) . . ?
O C5 H5A 111.9 . . ?
C6 C5 H5A 111.9 . . ?
C4 C5 H5A 111.9 . . ?
C5 C6 C7 102.0(3) . . ?
C5 C6 H6A 111.4 . . ?
C7 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C7 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
C1 C7 C6 104.8(3) . . ?
C1 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C1 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C1 C8 C9 115.3(2) . . ?
C1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C1 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C14 117.3(3) . . ?
C10 C9 C8 121.5(3) . . ?
C14 C9 C8 121.2(3) . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C9 121.6(3) . . ?
C13 C14 H14A 119.2 . . ?
C9 C14 H14A 119.2 . . ?
C16 C15 C20 116.8(3) . . ?
C16 C15 C3 122.0(3) . . ?
C20 C15 C3 121.2(3) . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16A 119.3 . . ?
C17 C16 H16A 119.3 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18A 120.5 . . ?
C19 C18 H18A 120.5 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C19 C20 C15 121.7(4) . . ?
C19 C20 H20A 119.1 . . ?
C15 C20 H20A 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.853
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_012b
_database_code_depnum_ccdc_archive 'CCDC 1057790'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H16 O'
_chemical_formula_sum            'C18 H16 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      299(2)
_chemical_formula_weight         248.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5946(4)
_cell_length_b                   9.1084(7)
_cell_length_c                   26.337(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.820(3)
_cell_angle_gamma                90.00
_cell_volume                     1341.93(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7908
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         26.38
_reflns_number_total             2703
_reflns_number_gt                2020
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.6564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2703
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1822
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O -0.1532(3) 0.4903(2) 0.10819(7) 0.0588(5) Uani 1 1 d . . .
C1 C 0.1624(4) 0.6191(2) 0.07622(8) 0.0435(5) Uani 1 1 d . . .
C2 C 0.3460(4) 0.6620(3) 0.04483(8) 0.0524(6) Uani 1 1 d . . .
H2A H 0.4609 0.5950 0.0344 0.063 Uiso 1 1 calc R . .
C3 C 0.3542(5) 0.8073(3) 0.02927(10) 0.0607(7) Uani 1 1 d . . .
H3A H 0.4752 0.8379 0.0079 0.073 Uiso 1 1 calc R . .
C4 C 0.1861(5) 0.9069(3) 0.04503(10) 0.0622(7) Uani 1 1 d . . .
H4A H 0.1940 1.0036 0.0339 0.075 Uiso 1 1 calc R . .
C5 C 0.0046(5) 0.8648(3) 0.07748(10) 0.0564(6) Uani 1 1 d . . .
H5A H -0.1072 0.9326 0.0887 0.068 Uiso 1 1 calc R . .
C6 C -0.0058(4) 0.7202(3) 0.09264(8) 0.0461(6) Uani 1 1 d . . .
C7 C -0.1699(4) 0.6379(3) 0.12755(9) 0.0514(6) Uani 1 1 d . . .
H7A H -0.3340 0.6752 0.1252 0.062 Uiso 1 1 calc R . .
C8 C -0.0758(4) 0.6398(3) 0.18174(9) 0.0519(6) Uani 1 1 d . . .
H8A H -0.0370 0.7403 0.1907 0.062 Uiso 1 1 calc R . .
H8B H -0.2028 0.6079 0.2039 0.062 Uiso 1 1 calc R . .
C9 C 0.1296(4) 0.5507(2) 0.19159(8) 0.0434(5) Uani 1 1 d . . .
C10 C 0.2216(4) 0.4622(3) 0.15218(9) 0.0502(6) Uani 1 1 d . . .
H10A H 0.3510 0.3999 0.1580 0.060 Uiso 1 1 calc R . .
C11 C 0.1015(4) 0.4724(3) 0.10008(9) 0.0483(6) Uani 1 1 d . . .
C12 C 0.1459(6) 0.3399(3) 0.06701(11) 0.0702(8) Uani 1 1 d . . .
H12A H 0.0669 0.3530 0.0347 0.105 Uiso 1 1 calc R . .
H12B H 0.0844 0.2537 0.0833 0.105 Uiso 1 1 calc R . .
H12C H 0.3146 0.3287 0.0620 0.105 Uiso 1 1 calc R . .
C13 C 0.2445(4) 0.5506(3) 0.24302(8) 0.0450(5) Uani 1 1 d . . .
C14 C 0.1813(5) 0.6499(3) 0.28023(9) 0.0617(7) Uani 1 1 d . . .
H14A H 0.0599 0.7171 0.2734 0.074 Uiso 1 1 calc R . .
C15 C 0.2942(6) 0.6519(4) 0.32749(10) 0.0726(8) Uani 1 1 d . . .
H15A H 0.2489 0.7207 0.3516 0.087 Uiso 1 1 calc R . .
C16 C 0.4702(6) 0.5542(4) 0.33870(10) 0.0707(8) Uani 1 1 d . . .
H16A H 0.5470 0.5563 0.3703 0.085 Uiso 1 1 calc R . .
C17 C 0.5339(6) 0.4523(4) 0.30304(12) 0.0785(9) Uani 1 1 d . . .
H17A H 0.6530 0.3842 0.3106 0.094 Uiso 1 1 calc R . .
C18 C 0.4219(5) 0.4503(3) 0.25590(10) 0.0657(8) Uani 1 1 d . . .
H18A H 0.4666 0.3800 0.2322 0.079 Uiso 1 1 calc R . .


_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
O C7 1.441(3) . ?
O C11 1.453(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.391(3) . ?
C1 C11 1.517(3) . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.509(3) . ?
C7 C8 1.514(3) . ?
C7 H7A 0.9800 . ?
C8 C9 1.428(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.417(3) . ?
C9 C13 1.491(3) . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.511(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.383(3) . ?
C13 C18 1.387(3) . ?
C14 C15 1.388(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.357(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
C7 O C11 103.02(16) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 C11 132.0(2) . . ?
C6 C1 C11 107.31(19) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5A 120.8 . . ?
C4 C5 H5A 120.8 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C7 132.9(2) . . ?
C1 C6 C7 106.3(2) . . ?
O C7 C6 101.83(18) . . ?
O C7 C8 108.71(19) . . ?
C6 C7 C8 111.24(18) . . ?
O C7 H7A 111.5 . . ?
C6 C7 H7A 111.5 . . ?
C8 C7 H7A 111.5 . . ?
C9 C8 C7 115.7(2) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 C13 120.6(2) . . ?
C8 C9 C13 120.1(2) . . ?
C9 C10 C11 117.7(2) . . ?
C9 C10 H10A 121.1 . . ?
C11 C10 H10A 121.1 . . ?
O C11 C1 100.90(18) . . ?
O C11 C10 107.19(18) . . ?
C1 C11 C10 109.16(18) . . ?
O C11 C12 110.1(2) . . ?
C1 C11 C12 115.1(2) . . ?
C10 C11 C12 113.4(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 116.5(2) . . ?
C14 C13 C9 122.1(2) . . ?
C18 C13 C9 121.3(2) . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14A 119.1 . . ?
C15 C14 H14A 119.1 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C13 C18 C17 121.6(3) . . ?
C13 C18 H18A 119.2 . . ?
C17 C18 H18A 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.5(3) . . . . ?
C11 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C11 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C6 C7 -177.54(19) . . . . ?
C11 C1 C6 C7 1.0(2) . . . . ?
C11 O C7 C6 43.9(2) . . . . ?
C11 O C7 C8 -73.6(2) . . . . ?
C5 C6 C7 O 154.3(2) . . . . ?
C1 C6 C7 O -27.5(2) . . . . ?
C5 C6 C7 C8 -90.0(3) . . . . ?
C1 C6 C7 C8 88.2(2) . . . . ?
O C7 C8 C9 39.3(3) . . . . ?
C6 C7 C8 C9 -72.1(3) . . . . ?
C7 C8 C9 C10 -3.6(3) . . . . ?
C7 C8 C9 C13 176.80(19) . . . . ?
C8 C9 C10 C11 2.8(3) . . . . ?
C13 C9 C10 C11 -177.59(19) . . . . ?
C7 O C11 C1 -42.9(2) . . . . ?
C7 O C11 C10 71.3(2) . . . . ?
C7 O C11 C12 -164.96(19) . . . . ?
C2 C1 C11 O -156.1(2) . . . . ?
C6 C1 C11 O 25.6(2) . . . . ?
C2 C1 C11 C10 91.2(3) . . . . ?
C6 C1 C11 C10 -87.1(2) . . . . ?
C2 C1 C11 C12 -37.6(3) . . . . ?
C6 C1 C11 C12 144.1(2) . . . . ?
C9 C10 C11 O -36.9(3) . . . . ?
C9 C10 C11 C1 71.6(3) . . . . ?
C9 C10 C11 C12 -158.6(2) . . . . ?
C10 C9 C13 C14 170.8(2) . . . . ?
C8 C9 C13 C14 -9.5(3) . . . . ?
C10 C9 C13 C18 -9.0(3) . . . . ?
C8 C9 C13 C18 170.6(2) . . . . ?
C18 C13 C14 C15 1.8(4) . . . . ?
C9 C13 C14 C15 -178.0(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C14 C13 C18 C17 -1.7(4) . . . . ?
C9 C13 C18 C17 178.1(3) . . . . ?
C16 C17 C18 C13 0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.069
