# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_s2179lc
_audit_block_doi                 10.5517/cc1j9hnz
_database_code_depnum_ccdc_archive 'CCDC 1409311'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O2'
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   14.3210(8)
_cell_length_b                   8.9769(5)
_cell_length_c                   11.7100(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.660(2)
_cell_angle_gamma                90.00
_cell_volume                     1504.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3.78
_cell_measurement_theta_min      65.82
_cell_measurement_theta_max      2422

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         I\mS
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8918
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.78
_diffrn_reflns_theta_max         65.82
_reflns_number_total             2432
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

_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)+(0.0307P)²+0.4181P] 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     SHELXL
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(16)
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.82203(6) 0.98403(9) 0.10019(7) 0.0241(2) Uani 1 1 d . . .
C1 C 0.68721(8) 1.11331(13) 0.16327(9) 0.0202(3) Uani 1 1 d . . .
O2 O 0.54764(6) 1.15482(10) 0.26524(8) 0.0300(2) Uani 1 1 d . . .
C2 C 0.70351(8) 1.28227(13) 0.15115(10) 0.0220(3) Uani 1 1 d . . .
H2 H 0.6532 1.3460 0.1830 0.026 Uiso 1 1 calc R . .
C3 C 0.67355(9) 1.19122(15) 0.04905(10) 0.0254(3) Uani 1 1 d . . .
H3A H 0.7204 1.1725 -0.0099 0.030 Uiso 1 1 calc R . .
H3B H 0.6087 1.2041 0.0189 0.030 Uiso 1 1 calc R . .
C4 C 0.77334(8) 1.01820(12) 0.17978(10) 0.0187(2) Uani 1 1 d . . .
C5 C 0.79945(7) 0.97409(13) 0.29913(10) 0.0190(2) Uani 1 1 d . . .
C6 C 0.85705(8) 0.85012(14) 0.31689(10) 0.0222(3) Uani 1 1 d . . .
H6 H 0.8764 0.7926 0.2537 0.027 Uiso 1 1 calc R . .
C7 C 0.88587(8) 0.81123(15) 0.42651(11) 0.0262(3) Uani 1 1 d . . .
H7 H 0.9238 0.7255 0.4387 0.031 Uiso 1 1 calc R . .
C8 C 0.85964(9) 0.89699(15) 0.51905(11) 0.0280(3) Uani 1 1 d . . .
H8 H 0.8804 0.8708 0.5942 0.034 Uiso 1 1 calc R . .
C9 C 0.80312(9) 1.02076(15) 0.50160(11) 0.0276(3) Uani 1 1 d . . .
H9 H 0.7855 1.0798 0.5648 0.033 Uiso 1 1 calc R . .
C10 C 0.77231(8) 1.05846(14) 0.39229(10) 0.0225(3) Uani 1 1 d . . .
H10 H 0.7325 1.1421 0.3808 0.027 Uiso 1 1 calc R . .
C11 C 0.60062(8) 1.06539(14) 0.22280(10) 0.0211(3) Uani 1 1 d . . .
C12 C 0.57961(8) 0.90261(13) 0.22434(10) 0.0207(3) Uani 1 1 d . . .
C13 C 0.60342(8) 0.81176(14) 0.13281(10) 0.0224(3) Uani 1 1 d . . .
H13 H 0.6364 0.8525 0.0709 0.027 Uiso 1 1 calc R . .
C14 C 0.57899(8) 0.66186(14) 0.13204(11) 0.0250(3) Uani 1 1 d . . .
H14 H 0.5937 0.6009 0.0688 0.030 Uiso 1 1 calc R . .
C15 C 0.53312(8) 0.60176(15) 0.22371(11) 0.0265(3) Uani 1 1 d . . .
H15 H 0.5169 0.4992 0.2235 0.032 Uiso 1 1 calc R . .
C16 C 0.51067(8) 0.69114(16) 0.31624(10) 0.0270(3) Uani 1 1 d . . .
H16 H 0.4800 0.6491 0.3795 0.032 Uiso 1 1 calc R . .
C17 C 0.53295(8) 0.84096(15) 0.31614(10) 0.0247(3) Uani 1 1 d . . .
H17 H 0.5165 0.9021 0.3786 0.030 Uiso 1 1 calc R . .
C18 C 0.79849(8) 1.34444(14) 0.16432(10) 0.0225(3) Uani 1 1 d . . .
H18 H 0.8496 1.2862 0.1399 0.027 Uiso 1 1 calc R . .
C19 C 0.81592(8) 1.47732(16) 0.20843(10) 0.0265(3) Uani 1 1 d . . .
H19A H 0.7660 1.5377 0.2334 0.032 Uiso 1 1 calc R . .
H19B H 0.8784 1.5126 0.2152 0.032 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 C4 1.2193(14) . ?
C1 C11 1.5030(16) . ?
C1 C4 1.5080(17) . ?
C1 C3 1.5170(16) . ?
C1 C2 1.5418(17) . ?
O2 C11 1.2202(15) . ?
C2 C18 1.4742(17) . ?
C2 C3 1.5007(17) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.4898(17) . ?
C5 C10 1.3926(17) . ?
C5 C6 1.3972(17) . ?
C6 C7 1.3818(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3898(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3863(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3838(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4921(17) . ?
C12 C17 1.3964(17) . ?
C12 C13 1.3969(17) . ?
C13 C14 1.3903(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3841(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3933(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.321(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C4 117.47(10) . . ?
C11 C1 C3 117.00(10) . . ?
C4 C1 C3 117.27(10) . . ?
C11 C1 C2 116.97(10) . . ?
C4 C1 C2 116.31(10) . . ?
C3 C1 C2 58.75(8) . . ?
C18 C2 C3 122.09(10) . . ?
C18 C2 C1 120.30(10) . . ?
C3 C2 C1 59.80(8) . . ?
C18 C2 H2 114.6 . . ?
C3 C2 H2 114.6 . . ?
C1 C2 H2 114.6 . . ?
C2 C3 C1 61.45(7) . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3B 117.6 . . ?
C1 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
O1 C4 C5 121.11(10) . . ?
O1 C4 C1 121.88(10) . . ?
C5 C4 C1 116.93(10) . . ?
C10 C5 C6 119.57(11) . . ?
C10 C5 C4 121.48(10) . . ?
C6 C5 C4 118.84(10) . . ?
C7 C6 C5 119.92(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.27(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.93(12) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.10(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 120.19(11) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O2 C11 C12 120.76(11) . . ?
O2 C11 C1 122.12(11) . . ?
C12 C11 C1 117.08(10) . . ?
C17 C12 C13 119.48(11) . . ?
C17 C12 C11 119.90(11) . . ?
C13 C12 C11 120.58(11) . . ?
C14 C13 C12 120.20(11) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.82(12) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.27(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.07(11) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.12(11) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C19 C18 C2 123.10(11) . . ?
C19 C18 H18 118.5 . . ?
C2 C18 H18 118.5 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

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
C11 C1 C2 C18 141.50(11) . . . . ?
C4 C1 C2 C18 -4.50(16) . . . . ?
C3 C1 C2 C18 -111.82(13) . . . . ?
C11 C1 C2 C3 -106.68(11) . . . . ?
C4 C1 C2 C3 107.33(11) . . . . ?
C18 C2 C3 C1 108.91(12) . . . . ?
C11 C1 C3 C2 106.63(11) . . . . ?
C4 C1 C3 C2 -105.70(11) . . . . ?
C11 C1 C4 O1 135.43(11) . . . . ?
C3 C1 C4 O1 -12.09(16) . . . . ?
C2 C1 C4 O1 -78.75(14) . . . . ?
C11 C1 C4 C5 -47.73(14) . . . . ?
C3 C1 C4 C5 164.75(10) . . . . ?
C2 C1 C4 C5 98.09(12) . . . . ?
O1 C4 C5 C10 151.98(11) . . . . ?
C1 C4 C5 C10 -24.89(16) . . . . ?
O1 C4 C5 C6 -24.20(17) . . . . ?
C1 C4 C5 C6 158.93(10) . . . . ?
C10 C5 C6 C7 0.65(17) . . . . ?
C4 C5 C6 C7 176.91(10) . . . . ?
C5 C6 C7 C8 -1.54(17) . . . . ?
C6 C7 C8 C9 1.02(18) . . . . ?
C7 C8 C9 C10 0.41(18) . . . . ?
C8 C9 C10 C5 -1.30(18) . . . . ?
C6 C5 C10 C9 0.77(17) . . . . ?
C4 C5 C10 C9 -175.39(11) . . . . ?
C4 C1 C11 O2 141.85(12) . . . . ?
C3 C1 C11 O2 -70.54(15) . . . . ?
C2 C1 C11 O2 -3.75(16) . . . . ?
C4 C1 C11 C12 -40.41(14) . . . . ?
C3 C1 C11 C12 107.20(12) . . . . ?
C2 C1 C11 C12 173.99(10) . . . . ?
O2 C11 C12 C17 -33.00(17) . . . . ?
C1 C11 C12 C17 149.23(11) . . . . ?
O2 C11 C12 C13 144.85(11) . . . . ?
C1 C11 C12 C13 -32.92(16) . . . . ?
C17 C12 C13 C14 1.42(17) . . . . ?
C11 C12 C13 C14 -176.44(11) . . . . ?
C12 C13 C14 C15 -1.71(18) . . . . ?
C13 C14 C15 C16 0.54(18) . . . . ?
C14 C15 C16 C17 0.93(18) . . . . ?
C15 C16 C17 C12 -1.22(18) . . . . ?
C13 C12 C17 C16 0.05(17) . . . . ?
C11 C12 C17 C16 177.93(11) . . . . ?
C3 C2 C18 C19 142.07(12) . . . . ?
C1 C2 C18 C19 -146.68(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        65.82
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.026
####################################################################### 
# 
# 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_s2180lc
_audit_block_doi                 10.5517/cc1j9hp0
_database_code_depnum_ccdc_archive 'CCDC 1409312'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O2'
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.3155(3)
_cell_length_b                   7.7433(4)
_cell_length_c                   15.0935(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.579(3)
_cell_angle_gamma                90.00
_cell_volume                     725.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2402
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      65.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5323
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         I\mS
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8588
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         65.87
_reflns_number_total             2439
_reflns_number_gt                2402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

_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)+(0.0541P)²+0.1546P] 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     SHELXL
_refine_ls_extinction_coef       0.0060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.59472(18) 0.32920(15) 0.41805(8) 0.0178(3) Uani 1 1 d . . .
C1 C 0.3155(3) 0.4361(2) 0.31644(11) 0.0151(4) Uani 1 1 d . . .
O2 O -0.01624(18) 0.54383(17) 0.24310(8) 0.0224(3) Uani 1 1 d . . .
C2 C 0.3397(3) 0.5597(2) 0.39482(11) 0.0176(4) Uani 1 1 d . . .
H2A H 0.2218 0.5453 0.4294 0.021 Uiso 1 1 calc R . .
H2B H 0.3429 0.6811 0.3745 0.021 Uiso 1 1 calc R . .
C3 C 0.5585(3) 0.5046(2) 0.45088(12) 0.0181(4) Uani 1 1 d . . .
H3 H 0.5502 0.5011 0.5164 0.022 Uiso 1 1 calc R . .
C4 C 0.4597(2) 0.3063(2) 0.33709(11) 0.0158(4) Uani 1 1 d . . .
C5 C 0.4920(3) 0.1410(2) 0.29371(11) 0.0160(4) Uani 1 1 d . . .
C6 C 0.3169(3) 0.0413(2) 0.25363(12) 0.0186(4) Uani 1 1 d . . .
H6 H 0.1748 0.0798 0.2551 0.022 Uiso 1 1 calc R . .
C7 C 0.3479(3) -0.1129(2) 0.21172(12) 0.0210(4) Uani 1 1 d . . .
H7 H 0.2276 -0.1793 0.1837 0.025 Uiso 1 1 calc R . .
C8 C 0.5556(3) -0.1704(2) 0.21078(13) 0.0239(4) Uani 1 1 d . . .
H8 H 0.5774 -0.2761 0.1818 0.029 Uiso 1 1 calc R . .
C9 C 0.7312(3) -0.0743(3) 0.25198(14) 0.0262(4) Uani 1 1 d . . .
H9 H 0.8731 -0.1151 0.2521 0.031 Uiso 1 1 calc R . .
C10 C 0.7004(3) 0.0808(2) 0.29297(12) 0.0212(4) Uani 1 1 d . . .
H10 H 0.8212 0.1468 0.3208 0.025 Uiso 1 1 calc R . .
C11 C 0.1423(3) 0.4550(2) 0.23789(12) 0.0156(4) Uani 1 1 d . . .
C12 C 0.1598(3) 0.3720(2) 0.14978(11) 0.0166(4) Uani 1 1 d . . .
C13 C -0.0243(3) 0.2969(2) 0.09940(12) 0.0185(4) Uani 1 1 d . . .
H13 H -0.1559 0.2984 0.1214 0.022 Uiso 1 1 calc R . .
C14 C -0.0154(3) 0.2200(2) 0.01723(12) 0.0227(4) Uani 1 1 d . . .
H14 H -0.1395 0.1649 -0.0160 0.027 Uiso 1 1 calc R . .
C15 C 0.1751(3) 0.2234(3) -0.01669(12) 0.0232(4) Uani 1 1 d . . .
H15 H 0.1802 0.1725 -0.0735 0.028 Uiso 1 1 calc R . .
C16 C 0.3570(3) 0.3008(3) 0.03218(12) 0.0212(4) Uani 1 1 d . . .
H16 H 0.4861 0.3051 0.0083 0.025 Uiso 1 1 calc R . .
C17 C 0.3514(3) 0.3723(2) 0.11610(11) 0.0175(4) Uani 1 1 d . . .
H17 H 0.4781 0.4214 0.1506 0.021 Uiso 1 1 calc R . .
C18 C 0.7429(3) 0.6141(2) 0.43633(12) 0.0208(4) Uani 1 1 d . . .
H18 H 0.7727 0.6224 0.3770 0.025 Uiso 1 1 calc R . .
C19 C 0.8672(3) 0.7004(3) 0.50140(15) 0.0301(5) Uani 1 1 d . . .
H19A H 0.8411 0.6945 0.5613 0.036 Uiso 1 1 calc R . .
H19B H 0.9828 0.7684 0.4883 0.036 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 C4 1.367(2) . ?
O1 C3 1.478(2) . ?
C1 C4 1.354(2) . ?
C1 C11 1.465(2) . ?
C1 C2 1.507(2) . ?
O2 C11 1.229(2) . ?
C2 C3 1.542(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C18 1.489(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.469(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.499(2) . ?
C12 C13 1.394(2) . ?
C12 C17 1.396(2) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.321(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?

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
C4 O1 C3 108.01(12) . . ?
C4 C1 C11 129.13(15) . . ?
C4 C1 C2 108.89(14) . . ?
C11 C1 C2 121.64(14) . . ?
C1 C2 C3 101.91(13) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.3 . . ?
O1 C3 C18 107.50(13) . . ?
O1 C3 C2 104.38(13) . . ?
C18 C3 C2 114.07(15) . . ?
O1 C3 H3 110.2 . . ?
C18 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C1 C4 O1 113.11(15) . . ?
C1 C4 C5 133.39(15) . . ?
O1 C4 C5 113.35(14) . . ?
C6 C5 C10 119.05(16) . . ?
C6 C5 C4 120.82(15) . . ?
C10 C5 C4 120.13(15) . . ?
C7 C6 C5 120.64(15) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.71(16) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.23(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.11(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.24(17) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O2 C11 C1 120.00(15) . . ?
O2 C11 C12 119.35(14) . . ?
C1 C11 C12 120.62(14) . . ?
C13 C12 C17 119.60(15) . . ?
C13 C12 C11 118.23(14) . . ?
C17 C12 C11 122.15(14) . . ?
C14 C13 C12 120.04(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.04(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.12(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.10(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.03(15) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C19 C18 C3 123.55(18) . . ?
C19 C18 H18 118.2 . . ?
C3 C18 H18 118.2 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

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
C4 C1 C2 C3 14.66(17) . . . . ?
C11 C1 C2 C3 -171.48(15) . . . . ?
C4 O1 C3 C18 -104.38(15) . . . . ?
C4 O1 C3 C2 17.11(16) . . . . ?
C1 C2 C3 O1 -18.63(16) . . . . ?
C1 C2 C3 C18 98.41(16) . . . . ?
C11 C1 C4 O1 -177.88(16) . . . . ?
C2 C1 C4 O1 -4.62(18) . . . . ?
C11 C1 C4 C5 -2.7(3) . . . . ?
C2 C1 C4 C5 170.54(17) . . . . ?
C3 O1 C4 C1 -8.32(18) . . . . ?
C3 O1 C4 C5 175.51(12) . . . . ?
C1 C4 C5 C6 -38.6(3) . . . . ?
O1 C4 C5 C6 136.56(15) . . . . ?
C1 C4 C5 C10 141.99(19) . . . . ?
O1 C4 C5 C10 -42.9(2) . . . . ?
C10 C5 C6 C7 -1.5(2) . . . . ?
C4 C5 C6 C7 179.04(15) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C4 C5 C10 C9 -179.78(16) . . . . ?
C4 C1 C11 O2 154.56(17) . . . . ?
C2 C1 C11 O2 -17.9(3) . . . . ?
C4 C1 C11 C12 -27.6(3) . . . . ?
C2 C1 C11 C12 159.87(15) . . . . ?
O2 C11 C12 C13 -42.0(2) . . . . ?
C1 C11 C12 C13 140.22(16) . . . . ?
O2 C11 C12 C17 136.18(17) . . . . ?
C1 C11 C12 C17 -41.6(2) . . . . ?
C17 C12 C13 C14 1.3(3) . . . . ?
C11 C12 C13 C14 179.49(16) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C15 C16 C17 C12 -2.4(3) . . . . ?
C13 C12 C17 C16 1.1(2) . . . . ?
C11 C12 C17 C16 -176.98(16) . . . . ?
O1 C3 C18 C19 -123.66(19) . . . . ?
C2 C3 C18 C19 121.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        65.87
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_s2181lc
_audit_block_doi                 10.5517/cc1j9hq1
_database_code_depnum_ccdc_archive 'CCDC 1409313'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O2'
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   14.3185(10)
_cell_length_b                   8.9738(6)
_cell_length_c                   11.7148(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.675(3)
_cell_angle_gamma                90.00
_cell_volume                     1504.61(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2345
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      65.86

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         I\mS
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8708
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         65.86
_reflns_number_total             2353
_reflns_number_gt                2345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

_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)+(0.0276P)²+0.4216P] 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     SHELXL
_refine_ls_extinction_coef       0.0041(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.17796(6) 0.01588(10) 0.89990(7) 0.0250(2) Uani 1 1 d . . .
C1 C 0.31283(8) -0.11326(14) 0.83673(10) 0.0213(3) Uani 1 1 d . . .
O2 O 0.45241(6) -0.15482(11) 0.73484(8) 0.0310(2) Uani 1 1 d . . .
C2 C 0.29645(9) -0.28231(14) 0.84890(10) 0.0229(3) Uani 1 1 d . . .
H2 H 0.3467 -0.3461 0.8171 0.027 Uiso 1 1 calc R . .
C3 C 0.32643(9) -0.19129(15) 0.95085(10) 0.0259(3) Uani 1 1 d . . .
H3A H 0.3912 -0.2043 0.9810 0.031 Uiso 1 1 calc R . .
H3B H 0.2796 -0.1726 1.0097 0.031 Uiso 1 1 calc R . .
C4 C 0.22674(8) -0.01832(13) 0.82012(10) 0.0197(3) Uani 1 1 d . . .
C5 C 0.20055(8) 0.02578(14) 0.70102(10) 0.0198(3) Uani 1 1 d . . .
C6 C 0.14309(8) 0.14994(14) 0.68315(10) 0.0228(3) Uani 1 1 d . . .
H6 H 0.1239 0.2076 0.7463 0.027 Uiso 1 1 calc R . .
C7 C 0.11416(8) 0.18890(15) 0.57370(11) 0.0266(3) Uani 1 1 d . . .
H7 H 0.0762 0.2746 0.5616 0.032 Uiso 1 1 calc R . .
C8 C 0.14040(9) 0.10307(15) 0.48101(11) 0.0291(3) Uani 1 1 d . . .
H8 H 0.1196 0.1293 0.4059 0.035 Uiso 1 1 calc R . .
C9 C 0.19680(9) -0.02061(15) 0.49848(11) 0.0280(3) Uani 1 1 d . . .
H9 H 0.2144 -0.0797 0.4353 0.034 Uiso 1 1 calc R . .
C10 C 0.22756(8) -0.05841(14) 0.60777(10) 0.0233(3) Uani 1 1 d . . .
H10 H 0.2673 -0.1422 0.6192 0.028 Uiso 1 1 calc R . .
C11 C 0.39944(8) -0.06544(14) 0.77728(10) 0.0219(3) Uani 1 1 d . . .
C12 C 0.42042(8) 0.09753(14) 0.77587(10) 0.0215(3) Uani 1 1 d . . .
C13 C 0.39669(8) 0.18832(15) 0.86712(10) 0.0234(3) Uani 1 1 d . . .
H13 H 0.3637 0.1475 0.9290 0.028 Uiso 1 1 calc R . .
C14 C 0.42101(9) 0.33802(15) 0.86805(11) 0.0258(3) Uani 1 1 d . . .
H14 H 0.4063 0.3990 0.9313 0.031 Uiso 1 1 calc R . .
C15 C 0.46692(8) 0.39824(15) 0.77618(11) 0.0272(3) Uani 1 1 d . . .
H15 H 0.4832 0.5009 0.7763 0.033 Uiso 1 1 calc R . .
C16 C 0.48926(8) 0.30887(16) 0.68391(11) 0.0278(3) Uani 1 1 d . . .
H16 H 0.5199 0.3509 0.6207 0.033 Uiso 1 1 calc R . .
C17 C 0.46701(8) 0.15907(15) 0.68393(11) 0.0255(3) Uani 1 1 d . . .
H17 H 0.4834 0.0979 0.6214 0.031 Uiso 1 1 calc R . .
C18 C 0.20159(9) -0.34445(14) 0.83574(10) 0.0233(3) Uani 1 1 d . . .
H18 H 0.1505 -0.2862 0.8602 0.028 Uiso 1 1 calc R . .
C19 C 0.18412(9) -0.47722(16) 0.79163(11) 0.0270(3) Uani 1 1 d . . .
H19A H 0.2340 -0.5376 0.7666 0.032 Uiso 1 1 calc R . .
H19B H 0.1216 -0.5124 0.7849 0.032 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 C4 1.2221(14) . ?
C1 C11 1.5026(16) . ?
C1 C4 1.5064(17) . ?
C1 C3 1.5167(17) . ?
C1 C2 1.5423(18) . ?
O2 C11 1.2198(15) . ?
C2 C18 1.4722(17) . ?
C2 C3 1.4992(18) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.4877(17) . ?
C5 C10 1.3923(17) . ?
C5 C6 1.3972(18) . ?
C6 C7 1.3809(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3839(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4931(18) . ?
C12 C13 1.3940(18) . ?
C12 C17 1.3972(17) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3870(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.320(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C4 117.52(10) . . ?
C11 C1 C3 117.00(10) . . ?
C4 C1 C3 117.29(10) . . ?
C11 C1 C2 116.97(10) . . ?
C4 C1 C2 116.24(10) . . ?
C3 C1 C2 58.69(8) . . ?
C18 C2 C3 122.11(11) . . ?
C18 C2 C1 120.34(11) . . ?
C3 C2 C1 59.80(8) . . ?
C18 C2 H2 114.6 . . ?
C3 C2 H2 114.6 . . ?
C1 C2 H2 114.6 . . ?
C2 C3 C1 61.51(8) . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3B 117.6 . . ?
C1 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
O1 C4 C5 121.09(11) . . ?
O1 C4 C1 121.81(11) . . ?
C5 C4 C1 117.03(10) . . ?
C10 C5 C6 119.41(11) . . ?
C10 C5 C4 121.56(11) . . ?
C6 C5 C4 118.93(10) . . ?
C7 C6 C5 120.03(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.25(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.87(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.12(12) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.31(12) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
O2 C11 C12 120.79(11) . . ?
O2 C11 C1 122.18(12) . . ?
C12 C11 C1 116.99(10) . . ?
C13 C12 C17 119.51(11) . . ?
C13 C12 C11 120.69(11) . . ?
C17 C12 C11 119.76(11) . . ?
C14 C13 C12 120.34(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.71(12) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.23(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.18(11) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.00(12) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C19 C18 C2 123.14(11) . . ?
C19 C18 H18 118.4 . . ?
C2 C18 H18 118.4 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

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
C11 C1 C2 C18 -141.50(11) . . . . ?
C4 C1 C2 C18 4.48(16) . . . . ?
C3 C1 C2 C18 111.84(13) . . . . ?
C11 C1 C2 C3 106.65(12) . . . . ?
C4 C1 C2 C3 -107.36(11) . . . . ?
C18 C2 C3 C1 -108.95(13) . . . . ?
C11 C1 C3 C2 -106.61(12) . . . . ?
C4 C1 C3 C2 105.58(12) . . . . ?
C11 C1 C4 O1 -135.45(12) . . . . ?
C3 C1 C4 O1 12.19(17) . . . . ?
C2 C1 C4 O1 78.76(15) . . . . ?
C11 C1 C4 C5 47.69(15) . . . . ?
C3 C1 C4 C5 -164.67(10) . . . . ?
C2 C1 C4 C5 -98.10(12) . . . . ?
O1 C4 C5 C10 -151.97(12) . . . . ?
C1 C4 C5 C10 24.92(16) . . . . ?
O1 C4 C5 C6 24.36(17) . . . . ?
C1 C4 C5 C6 -158.75(10) . . . . ?
C10 C5 C6 C7 -0.49(17) . . . . ?
C4 C5 C6 C7 -176.90(11) . . . . ?
C5 C6 C7 C8 1.36(18) . . . . ?
C6 C7 C8 C9 -0.91(18) . . . . ?
C7 C8 C9 C10 -0.41(19) . . . . ?
C8 C9 C10 C5 1.28(19) . . . . ?
C6 C5 C10 C9 -0.83(18) . . . . ?
C4 C5 C10 C9 175.49(11) . . . . ?
C4 C1 C11 O2 -141.75(12) . . . . ?
C3 C1 C11 O2 70.52(15) . . . . ?
C2 C1 C11 O2 3.80(17) . . . . ?
C4 C1 C11 C12 40.50(15) . . . . ?
C3 C1 C11 C12 -107.24(13) . . . . ?
C2 C1 C11 C12 -173.96(11) . . . . ?
O2 C11 C12 C13 -144.85(12) . . . . ?
C1 C11 C12 C13 32.94(16) . . . . ?
O2 C11 C12 C17 33.06(18) . . . . ?
C1 C11 C12 C17 -149.15(11) . . . . ?
C17 C12 C13 C14 -1.49(18) . . . . ?
C11 C12 C13 C14 176.43(11) . . . . ?
C12 C13 C14 C15 1.75(18) . . . . ?
C13 C14 C15 C16 -0.56(18) . . . . ?
C14 C15 C16 C17 -0.91(18) . . . . ?
C15 C16 C17 C12 1.17(18) . . . . ?
C13 C12 C17 C16 0.02(18) . . . . ?
C11 C12 C17 C16 -177.92(11) . . . . ?
C3 C2 C18 C19 -142.11(13) . . . . ?
C1 C2 C18 C19 146.59(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        65.86
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_s2182lc
_audit_block_doi                 10.5517/cc1j9hr2
_database_code_depnum_ccdc_archive 'CCDC 1409314'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O2'
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.309(2)
_cell_length_b                   7.753(2)
_cell_length_c                   15.117(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.736(14)
_cell_angle_gamma                90.00
_cell_volume                     726.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2381
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      65.60

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         I\mS
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8149
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         65.60
_reflns_number_total             2402
_reflns_number_gt                2381
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Shledrick, 1991)'
_computing_publication_material  ?

_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)+(0.0189P)²+0.1712P] 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     SHELXL
_refine_ls_extinction_coef       0.0085(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
O1 O 0.40543(14) 0.67093(11) 0.58216(6) 0.0201(2) Uani 1 1 d . . .
C1 C 0.6846(2) 0.56407(16) 0.68385(8) 0.0176(3) Uani 1 1 d . . .
O2 O 1.01651(14) 0.45632(12) 0.75682(6) 0.0245(2) Uani 1 1 d . . .
C2 C 0.6601(2) 0.44062(17) 0.60497(8) 0.0200(3) Uani 1 1 d . . .
H2A H 0.6573 0.3192 0.6250 0.024 Uiso 1 1 calc R . .
H2B H 0.7777 0.4555 0.5705 0.024 Uiso 1 1 calc R . .
C3 C 0.4420(2) 0.49500(16) 0.54945(8) 0.0201(3) Uani 1 1 d . . .
H3 H 0.4503 0.4987 0.4841 0.024 Uiso 1 1 calc R . .
C4 C 0.53971(19) 0.69329(16) 0.66270(8) 0.0172(3) Uani 1 1 d . . .
C5 C 0.5073(2) 0.85887(16) 0.70647(8) 0.0175(3) Uani 1 1 d . . .
C6 C 0.6831(2) 0.95870(17) 0.74637(8) 0.0200(3) Uani 1 1 d . . .
H6 H 0.8254 0.9206 0.7447 0.024 Uiso 1 1 calc R . .
C7 C 0.6520(2) 1.11310(17) 0.78840(9) 0.0223(3) Uani 1 1 d . . .
H7 H 0.7726 1.1793 0.8165 0.027 Uiso 1 1 calc R . .
C8 C 0.4446(2) 1.17057(18) 0.78931(9) 0.0256(3) Uani 1 1 d . . .
H8 H 0.4231 1.2762 0.8182 0.031 Uiso 1 1 calc R . .
C9 C 0.2685(2) 1.07470(18) 0.74827(10) 0.0282(3) Uani 1 1 d . . .
H9 H 0.1265 1.1152 0.7484 0.034 Uiso 1 1 calc R . .
C10 C 0.2996(2) 0.91898(17) 0.70682(9) 0.0234(3) Uani 1 1 d . . .
H10 H 0.1785 0.8534 0.6786 0.028 Uiso 1 1 calc R . .
C11 C 0.8566(2) 0.54534(16) 0.76207(8) 0.0179(3) Uani 1 1 d . . .
C12 C 0.83968(19) 0.62809(16) 0.85017(8) 0.0171(3) Uani 1 1 d . . .
C13 C 1.0238(2) 0.70278(17) 0.90073(8) 0.0209(3) Uani 1 1 d . . .
H13 H 1.1557 0.7009 0.8790 0.025 Uiso 1 1 calc R . .
C14 C 1.0150(2) 0.77990(18) 0.98269(9) 0.0238(3) Uani 1 1 d . . .
H14 H 1.1392 0.8354 1.0157 0.029 Uiso 1 1 calc R . .
C15 C 0.8252(2) 0.77627(18) 1.01682(9) 0.0249(3) Uani 1 1 d . . .
H15 H 0.8206 0.8268 1.0737 0.030 Uiso 1 1 calc R . .
C16 C 0.6428(2) 0.69876(18) 0.96776(9) 0.0234(3) Uani 1 1 d . . .
H16 H 0.5136 0.6944 0.9914 0.028 Uiso 1 1 calc R . .
C17 C 0.6487(2) 0.62743(16) 0.88398(8) 0.0190(3) Uani 1 1 d . . .
H17 H 0.5220 0.5779 0.8496 0.023 Uiso 1 1 calc R . .
C18 C 0.2567(2) 0.38594(18) 0.56333(9) 0.0230(3) Uani 1 1 d . . .
H18 H 0.2261 0.3780 0.6224 0.028 Uiso 1 1 calc R . .
C19 C 0.1331(2) 0.3001(2) 0.49860(11) 0.0324(4) Uani 1 1 d . . .
H19A H 0.1598 0.3056 0.4389 0.039 Uiso 1 1 calc R . .
H19B H 0.0170 0.2325 0.5115 0.039 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 C4 1.3586(15) . ?
O1 C3 1.4835(15) . ?
C1 C4 1.3540(18) . ?
C1 C11 1.4553(18) . ?
C1 C2 1.5143(17) . ?
O2 C11 1.2373(16) . ?
C2 C3 1.5312(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C18 1.4894(19) . ?
C3 H3 1.0000 . ?
C4 C5 1.4758(18) . ?
C5 C10 1.3921(19) . ?
C5 C6 1.3942(18) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4999(17) . ?
C12 C13 1.3922(18) . ?
C12 C17 1.3936(18) . ?
C13 C14 1.3861(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3888(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.313(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?

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
C4 O1 C3 107.83(9) . . ?
C4 C1 C11 129.35(11) . . ?
C4 C1 C2 108.43(11) . . ?
C11 C1 C2 121.88(11) . . ?
C1 C2 C3 101.96(10) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?
O1 C3 C18 107.46(10) . . ?
O1 C3 C2 104.49(10) . . ?
C18 C3 C2 114.54(11) . . ?
O1 C3 H3 110.0 . . ?
C18 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
C1 C4 O1 113.46(11) . . ?
C1 C4 C5 132.97(11) . . ?
O1 C4 C5 113.42(10) . . ?
C10 C5 C6 119.09(12) . . ?
C10 C5 C4 120.13(11) . . ?
C6 C5 C4 120.76(11) . . ?
C7 C6 C5 120.56(12) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.81(12) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 120.26(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.96(13) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.28(12) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O2 C11 C1 119.80(11) . . ?
O2 C11 C12 119.29(11) . . ?
C1 C11 C12 120.89(11) . . ?
C13 C12 C17 119.35(11) . . ?
C13 C12 C11 118.38(11) . . ?
C17 C12 C11 122.23(11) . . ?
C14 C13 C12 120.12(12) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.26(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.83(12) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.03(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.33(12) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C3 123.75(13) . . ?
C19 C18 H18 118.1 . . ?
C3 C18 H18 118.1 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

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
C4 C1 C2 C3 -14.87(13) . . . . ?
C11 C1 C2 C3 171.19(12) . . . . ?
C4 O1 C3 C18 104.62(11) . . . . ?
C4 O1 C3 C2 -17.45(12) . . . . ?
C1 C2 C3 O1 18.92(12) . . . . ?
C1 C2 C3 C18 -98.37(12) . . . . ?
C11 C1 C4 O1 177.93(12) . . . . ?
C2 C1 C4 O1 4.59(14) . . . . ?
C11 C1 C4 C5 2.7(2) . . . . ?
C2 C1 C4 C5 -170.64(12) . . . . ?
C3 O1 C4 C1 8.45(13) . . . . ?
C3 O1 C4 C5 -175.36(10) . . . . ?
C1 C4 C5 C10 -142.14(14) . . . . ?
O1 C4 C5 C10 42.64(16) . . . . ?
C1 C4 C5 C6 39.1(2) . . . . ?
O1 C4 C5 C6 -136.11(11) . . . . ?
C10 C5 C6 C7 2.06(18) . . . . ?
C4 C5 C6 C7 -179.19(11) . . . . ?
C5 C6 C7 C8 -1.27(19) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C6 C5 C10 C9 -1.45(19) . . . . ?
C4 C5 C10 C9 179.79(12) . . . . ?
C4 C1 C11 O2 -154.48(13) . . . . ?
C2 C1 C11 O2 18.08(19) . . . . ?
C4 C1 C11 C12 27.5(2) . . . . ?
C2 C1 C11 C12 -159.98(11) . . . . ?
O2 C11 C12 C13 41.75(17) . . . . ?
C1 C11 C12 C13 -140.18(12) . . . . ?
O2 C11 C12 C17 -136.11(13) . . . . ?
C1 C11 C12 C17 41.96(18) . . . . ?
C17 C12 C13 C14 -1.81(18) . . . . ?
C11 C12 C13 C14 -179.73(12) . . . . ?
C12 C13 C14 C15 2.9(2) . . . . ?
C13 C14 C15 C16 -1.5(2) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C15 C16 C17 C12 2.2(2) . . . . ?
C13 C12 C17 C16 -0.76(18) . . . . ?
C11 C12 C17 C16 177.08(12) . . . . ?
O1 C3 C18 C19 123.69(14) . . . . ?
C2 C3 C18 C19 -120.72(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        65.60
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.027
