# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Kar, Tanusree'
_publ_contact_author_email       mstk@iacs.res.in

_publ_section_title              
;
Insight in supramolecular self-assembly directed by weak
interactions in acetophenone derivatives: Crystal
structures and Hirshfeld surface analyses
;
loop_
_publ_author_name
S.Seth
D.Sarkar
A.Roy
T.Kar

data_a-9
_database_code_depnum_ccdc_archive 'CCDC 824672'
#TrackingRef 'Compound-1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 O2'
_chemical_formula_weight         150.17

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   P21/c

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                   7.730(2)
_cell_length_b                   7.2650(10)
_cell_length_c                   15.295(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.818(8)
_cell_angle_gamma                90.00
_cell_volume                     773.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    980
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       flake
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7011
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1361
_reflns_number_gt                1238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0297P)^2^+0.3557P] where P=(Fo^2^+2Fc^2^)/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       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1361
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.80221(12) 1.07212(12) 0.20031(6) 0.0252(2) Uani 1 1 d . . .
H1 H 0.8247 0.9892 0.2402 0.038 Uiso 1 1 d R . .
O2 O 0.84587(13) 0.64750(12) -0.15141(6) 0.0298(3) Uani 1 1 d . . .
C1 C 0.80235(16) 1.00301(16) 0.11791(8) 0.0199(3) Uani 1 1 d . . .
C2 C 0.72532(16) 1.11557(16) 0.03552(9) 0.0200(3) Uani 1 1 d . . .
C3 C 0.71679(16) 1.04539(16) -0.05027(8) 0.0204(3) Uani 1 1 d . . .
H3 H 0.6628 1.1172 -0.1061 0.025 Uiso 1 1 calc R . .
C4 C 0.78646(16) 0.87027(16) -0.05619(8) 0.0202(3) Uani 1 1 d . . .
C5 C 0.87096(16) 0.76524(16) 0.02838(9) 0.0214(3) Uani 1 1 d . . .
H5 H 0.9228 0.6506 0.0266 0.026 Uiso 1 1 calc R . .
C6 C 0.87814(16) 0.83034(16) 0.11456(9) 0.0212(3) Uani 1 1 d . . .
H6 H 0.9336 0.7591 0.1705 0.025 Uiso 1 1 calc R . .
C7 C 0.65550(18) 1.30539(17) 0.04183(9) 0.0256(3) Uani 1 1 d . . .
H7A H 0.6107 1.3646 -0.0203 0.038 Uiso 1 1 calc R . .
H7B H 0.7589 1.3757 0.0893 0.038 Uiso 1 1 calc R . .
H7C H 0.5522 1.2975 0.0605 0.038 Uiso 1 1 calc R . .
C8 C 0.77111(17) 0.79591(17) -0.14885(9) 0.0232(3) Uani 1 1 d . . .
C9 C 0.65922(19) 0.9017(2) -0.24103(9) 0.0306(3) Uani 1 1 d . . .
H9A H 0.6547 0.8324 -0.2954 0.046 Uiso 1 1 calc R . .
H9B H 0.7207 1.0179 -0.2380 0.046 Uiso 1 1 calc R . .
H9C H 0.5308 0.9223 -0.2485 0.046 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0355(5) 0.0231(5) 0.0191(5) -0.0002(3) 0.0137(4) -0.0005(4)
O2 0.0376(5) 0.0280(5) 0.0268(5) -0.0044(4) 0.0167(4) 0.0014(4)
C1 0.0190(6) 0.0224(6) 0.0193(6) -0.0024(5) 0.0094(5) -0.0052(5)
C2 0.0175(6) 0.0206(6) 0.0223(6) 0.0000(5) 0.0089(5) -0.0024(5)
C3 0.0186(6) 0.0238(6) 0.0179(6) 0.0030(5) 0.0070(5) -0.0014(5)
C4 0.0181(6) 0.0226(6) 0.0209(6) -0.0014(5) 0.0094(5) -0.0045(5)
C5 0.0217(6) 0.0185(6) 0.0261(7) -0.0007(5) 0.0124(5) -0.0014(5)
C6 0.0214(6) 0.0217(6) 0.0205(6) 0.0048(5) 0.0090(5) -0.0004(5)
C7 0.0291(7) 0.0228(6) 0.0261(7) 0.0016(5) 0.0131(6) 0.0024(5)
C8 0.0201(6) 0.0271(7) 0.0240(7) -0.0037(5) 0.0112(5) -0.0056(5)
C9 0.0310(7) 0.0403(8) 0.0197(6) -0.0033(6) 0.0103(6) 0.0024(6)

_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 1.3571(14) . ?
O1 H1 0.8200 . ?
O2 C8 1.2320(15) . ?
C1 C6 1.3948(17) . ?
C1 C2 1.3991(17) . ?
C2 C3 1.3823(16) . ?
C2 C7 1.4993(17) . ?
C3 C4 1.3997(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3950(17) . ?
C4 C8 1.4724(17) . ?
C5 C6 1.3787(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.5048(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C6 122.48(11) . . ?
O1 C1 C2 116.61(11) . . ?
C6 C1 C2 120.89(11) . . ?
C3 C2 C1 117.71(11) . . ?
C3 C2 C7 122.05(11) . . ?
C1 C2 C7 120.24(11) . . ?
C2 C3 C4 122.41(11) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 118.37(11) . . ?
C5 C4 C8 120.04(11) . . ?
C3 C4 C8 121.58(11) . . ?
C6 C5 C4 120.43(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.06(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C4 120.63(11) . . ?
O2 C8 C9 120.22(11) . . ?
C4 C8 C9 119.14(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.47(10) . . . . ?
C6 C1 C2 C3 3.72(16) . . . . ?
O1 C1 C2 C7 2.59(16) . . . . ?
C6 C1 C2 C7 -176.23(10) . . . . ?
C1 C2 C3 C4 -1.73(17) . . . . ?
C7 C2 C3 C4 178.21(11) . . . . ?
C2 C3 C4 C5 -1.36(17) . . . . ?
C2 C3 C4 C8 178.25(10) . . . . ?
C3 C4 C5 C6 2.56(17) . . . . ?
C8 C4 C5 C6 -177.06(10) . . . . ?
C4 C5 C6 C1 -0.63(17) . . . . ?
O1 C1 C6 C5 178.66(10) . . . . ?
C2 C1 C6 C5 -2.60(17) . . . . ?
C5 C4 C8 O2 -5.85(17) . . . . ?
C3 C4 C8 O2 174.54(11) . . . . ?
C5 C4 C8 C9 172.90(11) . . . . ?
C3 C4 C8 C9 -6.71(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.88 2.6714(12) 162.5 4_576
C6 H6 O1 0.93 2.53 3.3983(15) 155.4 2_745

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033

# Attachment 'Compound-2.cif'

data_a-10
_database_code_depnum_ccdc_archive 'CCDC 824673'
#TrackingRef 'Compound-2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29

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   P21/c

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                   8.1940(6)
_cell_length_b                   9.4980(7)
_cell_length_c                   17.3407(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.609(3)
_cell_angle_gamma                90.00
_cell_volume                     1263.20(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1700
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11563
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2233
_reflns_number_gt                2018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0491P)^2^+0.3972P] where P=(Fo^2^+2Fc^2^)/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         2233
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.46570(12) 0.81566(11) 1.04545(6) 0.0329(3) Uani 1 1 d . . .
O2 O 0.99149(11) 0.58654(9) 0.88512(5) 0.0238(2) Uani 1 1 d . . .
C1 C 0.91515(16) 0.65115(13) 0.93396(7) 0.0209(3) Uani 1 1 d . . .
C2 C 0.74964(16) 0.59835(13) 0.92559(7) 0.0209(3) Uani 1 1 d . . .
C3 C 0.65896(16) 0.66445(13) 0.96844(7) 0.0221(3) Uani 1 1 d . . .
H3 H 0.5485 0.6315 0.9629 0.027 Uiso 1 1 calc R . .
C4 C 0.72701(16) 0.77994(13) 1.02021(7) 0.0217(3) Uani 1 1 d . . .
C5 C 0.89397(16) 0.82562(13) 1.02973(7) 0.0234(3) Uani 1 1 d . . .
H5 H 0.9429 0.8999 1.0653 0.028 Uiso 1 1 calc R . .
C6 C 0.98869(16) 0.76218(14) 0.98704(8) 0.0238(3) Uani 1 1 d . . .
H6 H 1.1004 0.7936 0.9938 0.029 Uiso 1 1 calc R . .
C7 C 0.67714(17) 0.47499(14) 0.86982(8) 0.0264(3) Uani 1 1 d . . .
H7A H 0.5670 0.4482 0.8734 0.040 Uiso 1 1 calc R . .
H7B H 0.7569 0.3973 0.8864 0.040 Uiso 1 1 calc R . .
H7C H 0.6611 0.5006 0.8141 0.040 Uiso 1 1 calc R . .
C8 C 0.61812(17) 0.84831(14) 1.06221(8) 0.0250(3) Uani 1 1 d . . .
C9 C 0.69767(19) 0.96167(15) 1.12481(9) 0.0329(3) Uani 1 1 d . . .
H9A H 0.6222 0.9811 1.1551 0.049 Uiso 1 1 calc R . .
H9B H 0.7125 1.0457 1.0972 0.049 Uiso 1 1 calc R . .
H9C H 0.8090 0.9306 1.1620 0.049 Uiso 1 1 calc R . .
C10 C 1.14922(16) 0.64621(14) 0.88194(8) 0.0264(3) Uani 1 1 d . . .
H10A H 1.2438 0.6307 0.9338 0.032 Uiso 1 1 calc R . .
H10B H 1.1352 0.7469 0.8725 0.032 Uiso 1 1 calc R . .
C11 C 1.19020(15) 0.57736(14) 0.81315(7) 0.0228(3) Uani 1 1 d . . .
C12 C 1.16818(17) 0.43315(14) 0.79905(8) 0.0256(3) Uani 1 1 d . . .
H12 H 1.1232 0.3785 0.8314 0.031 Uiso 1 1 calc R . .
C13 C 1.21291(17) 0.37073(15) 0.73722(8) 0.0291(3) Uani 1 1 d . . .
H13 H 1.1983 0.2742 0.7283 0.035 Uiso 1 1 calc R . .
C14 C 1.27933(17) 0.45126(15) 0.68844(8) 0.0279(3) Uani 1 1 d . . .
H14 H 1.3099 0.4089 0.6471 0.034 Uiso 1 1 calc R . .
C15 C 1.29994(17) 0.59484(15) 0.70144(8) 0.0280(3) Uani 1 1 d . . .
H15 H 1.3437 0.6494 0.6686 0.034 Uiso 1 1 calc R . .
C16 C 1.25529(17) 0.65733(14) 0.76348(8) 0.0268(3) Uani 1 1 d . . .
H16 H 1.2691 0.7540 0.7719 0.032 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0266(5) 0.0394(6) 0.0371(6) -0.0090(4) 0.0167(4) -0.0057(4)
O2 0.0208(5) 0.0241(5) 0.0288(5) -0.0027(4) 0.0117(4) -0.0023(4)
C1 0.0201(6) 0.0219(6) 0.0204(6) 0.0042(5) 0.0066(5) 0.0025(5)
C2 0.0199(6) 0.0201(6) 0.0205(6) 0.0040(5) 0.0045(5) -0.0001(5)
C3 0.0178(6) 0.0248(7) 0.0228(6) 0.0028(5) 0.0061(5) -0.0023(5)
C4 0.0229(6) 0.0227(6) 0.0190(6) 0.0030(5) 0.0066(5) -0.0005(5)
C5 0.0248(7) 0.0237(7) 0.0199(6) -0.0011(5) 0.0057(5) -0.0044(5)
C6 0.0189(6) 0.0256(7) 0.0255(6) 0.0012(5) 0.0061(5) -0.0043(5)
C7 0.0222(7) 0.0257(7) 0.0311(7) -0.0037(5) 0.0091(6) -0.0024(5)
C8 0.0271(7) 0.0261(7) 0.0228(6) 0.0021(5) 0.0101(5) -0.0023(5)
C9 0.0355(8) 0.0336(8) 0.0336(8) -0.0080(6) 0.0173(6) -0.0057(6)
C10 0.0203(6) 0.0287(7) 0.0318(7) -0.0028(6) 0.0114(5) -0.0048(5)
C11 0.0166(6) 0.0271(7) 0.0229(6) 0.0004(5) 0.0046(5) 0.0006(5)
C12 0.0244(7) 0.0268(7) 0.0249(6) 0.0022(5) 0.0077(5) -0.0036(5)
C13 0.0299(7) 0.0259(7) 0.0291(7) -0.0052(5) 0.0076(6) -0.0038(5)
C14 0.0249(7) 0.0363(8) 0.0217(6) -0.0050(5) 0.0071(5) 0.0002(6)
C15 0.0263(7) 0.0329(8) 0.0264(7) 0.0070(6) 0.0113(5) 0.0020(6)
C16 0.0262(7) 0.0225(6) 0.0331(7) 0.0032(5) 0.0122(6) 0.0016(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.2185(16) . ?
O2 C1 1.3631(15) . ?
O2 C10 1.4300(15) . ?
C1 C6 1.3900(18) . ?
C1 C2 1.4047(17) . ?
C2 C3 1.3737(17) . ?
C2 C7 1.5023(18) . ?
C3 C4 1.4028(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3886(18) . ?
C4 C8 1.4851(18) . ?
C5 C6 1.3848(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.5048(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.4985(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.3880(18) . ?
C11 C12 1.3918(19) . ?
C12 C13 1.3828(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.3860(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3858(19) . ?
C15 H15 0.9300 . ?
C16 H16 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 O2 C10 117.66(10) . . ?
O2 C1 C6 124.49(11) . . ?
O2 C1 C2 114.37(11) . . ?
C6 C1 C2 121.13(11) . . ?
C3 C2 C1 117.87(11) . . ?
C3 C2 C7 122.55(11) . . ?
C1 C2 C7 119.58(11) . . ?
C2 C3 C4 122.33(11) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 118.26(11) . . ?
C5 C4 C8 122.82(12) . . ?
C3 C4 C8 118.93(11) . . ?
C6 C5 C4 120.97(12) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.36(11) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C4 120.93(12) . . ?
O1 C8 C9 120.10(12) . . ?
C4 C8 C9 118.95(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 108.45(10) . . ?
O2 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 118.94(12) . . ?
C16 C11 C10 119.86(12) . . ?
C12 C11 C10 121.18(11) . . ?
C13 C12 C11 120.31(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.32(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.75(12) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.90(12) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.76(13) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?

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
C10 O2 C1 C6 -6.74(17) . . . . ?
C10 O2 C1 C2 171.92(10) . . . . ?
O2 C1 C2 C3 -175.54(10) . . . . ?
C6 C1 C2 C3 3.18(18) . . . . ?
O2 C1 C2 C7 3.40(16) . . . . ?
C6 C1 C2 C7 -177.89(11) . . . . ?
C1 C2 C3 C4 -0.86(18) . . . . ?
C7 C2 C3 C4 -179.77(11) . . . . ?
C2 C3 C4 C5 -1.80(18) . . . . ?
C2 C3 C4 C8 178.02(11) . . . . ?
C3 C4 C5 C6 2.24(18) . . . . ?
C8 C4 C5 C6 -177.57(11) . . . . ?
C4 C5 C6 C1 -0.02(19) . . . . ?
O2 C1 C6 C5 175.81(11) . . . . ?
C2 C1 C6 C5 -2.77(19) . . . . ?
C5 C4 C8 O1 171.78(12) . . . . ?
C3 C4 C8 O1 -8.03(18) . . . . ?
C5 C4 C8 C9 -6.83(19) . . . . ?
C3 C4 C8 C9 173.36(12) . . . . ?
C1 O2 C10 C11 -168.94(10) . . . . ?
O2 C10 C11 C16 140.32(12) . . . . ?
O2 C10 C11 C12 -41.24(16) . . . . ?
C16 C11 C12 C13 0.89(19) . . . . ?
C10 C11 C12 C13 -177.56(12) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 0.45(19) . . . . ?
C14 C15 C16 C11 0.15(19) . . . . ?
C12 C11 C16 C15 -0.82(18) . . . . ?
C10 C11 C16 C15 177.66(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047

# Attachment 'Compound-3.cif'

data_d-15
_database_code_depnum_ccdc_archive 'CCDC 824674'
#TrackingRef 'Compound-3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.41

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

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

_cell_length_a                   8.149(4)
_cell_length_b                   8.793(3)
_cell_length_c                   12.745(3)
_cell_angle_alpha                92.070(2)
_cell_angle_beta                 95.979(3)
_cell_angle_gamma                92.462(2)
_cell_volume                     906.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2140
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8302
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3194
_reflns_number_gt                2598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0968P] where P=(Fo^2^+2Fc^2^)/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         3194
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O3 O 0.43215(12) -0.10668(12) 0.85250(8) 0.0230(3) Uani 1 1 d . . .
O2 O 0.16753(13) 0.14659(13) 0.57370(8) 0.0267(3) Uani 1 1 d . . .
O1 O 0.53421(14) 0.14379(13) 0.66881(10) 0.0328(3) Uani 1 1 d . . .
C2 C -0.00110(19) 0.05803(18) 0.70886(12) 0.0226(4) Uani 1 1 d . . .
H2 H -0.0958 0.0989 0.6763 0.027 Uiso 1 1 calc R . .
C3 C 0.14754(19) 0.07446(17) 0.66507(12) 0.0210(4) Uani 1 1 d . . .
C5 C 0.28255(18) -0.06005(16) 0.80788(12) 0.0200(4) Uani 1 1 d . . .
C6 C 0.13469(18) -0.07753(17) 0.85221(12) 0.0214(4) Uani 1 1 d . . .
H6 H 0.1309 -0.1274 0.9151 0.026 Uiso 1 1 calc R . .
C4 C 0.29072(18) 0.01327(17) 0.71350(12) 0.0204(4) Uani 1 1 d . . .
C8 C 0.45210(19) 0.02514(18) 0.66492(12) 0.0223(4) Uani 1 1 d . . .
C1 C -0.00803(19) -0.01980(17) 0.80169(12) 0.0219(4) Uani 1 1 d . . .
C17 C 0.4349(2) -0.19317(17) 0.94637(12) 0.0235(4) Uani 1 1 d . . .
H17B H 0.3737 -0.1410 0.9970 0.028 Uiso 1 1 calc R . .
H17A H 0.5482 -0.1976 0.9776 0.028 Uiso 1 1 calc R . .
C18 C 0.36178(18) -0.35329(17) 0.92539(12) 0.0216(4) Uani 1 1 d . . .
C10 C 0.03695(19) 0.24097(18) 0.53264(13) 0.0248(4) Uani 1 1 d . . .
H10A H 0.0007 0.3035 0.5893 0.030 Uiso 1 1 calc R . .
H10B H -0.0567 0.1777 0.5006 0.030 Uiso 1 1 calc R . .
C20 C 0.1970(2) -0.56712(19) 0.97581(14) 0.0297(4) Uani 1 1 d . . .
H20 H 0.1295 -0.6099 1.0225 0.036 Uiso 1 1 calc R . .
C15 C 0.3036(2) 0.5280(2) 0.40388(14) 0.0312(4) Uani 1 1 d . . .
H15 H 0.3984 0.5900 0.4221 0.037 Uiso 1 1 calc R . .
C16 C 0.2441(2) 0.43373(19) 0.47772(14) 0.0284(4) Uani 1 1 d . . .
H16 H 0.2994 0.4331 0.5453 0.034 Uiso 1 1 calc R . .
C11 C 0.10279(19) 0.34013(17) 0.45181(12) 0.0226(4) Uani 1 1 d . . .
C7 C -0.1703(2) -0.0468(2) 0.84590(14) 0.0300(4) Uani 1 1 d . . .
H7A H -0.2384 0.0380 0.8315 0.045 Uiso 1 1 calc R . .
H7B H -0.1511 -0.0573 0.9208 0.045 Uiso 1 1 calc R . .
H7C H -0.2251 -0.1382 0.8136 0.045 Uiso 1 1 calc R . .
C23 C 0.4013(2) -0.44061(19) 0.83932(13) 0.0290(4) Uani 1 1 d . . .
H23 H 0.4708 -0.3988 0.7934 0.035 Uiso 1 1 calc R . .
C9 C 0.5011(2) -0.1169(2) 0.61044(14) 0.0321(4) Uani 1 1 d . . .
H9A H 0.4266 -0.1394 0.5478 0.048 Uiso 1 1 calc R . .
H9B H 0.4964 -0.2001 0.6569 0.048 Uiso 1 1 calc R . .
H9C H 0.6115 -0.1023 0.5916 0.048 Uiso 1 1 calc R . .
C14 C 0.2217(2) 0.5299(2) 0.30294(14) 0.0324(4) Uani 1 1 d . . .
H14 H 0.2619 0.5923 0.2531 0.039 Uiso 1 1 calc R . .
C19 C 0.2589(2) -0.41820(19) 0.99317(13) 0.0267(4) Uani 1 1 d . . .
H19 H 0.2310 -0.3610 1.0510 0.032 Uiso 1 1 calc R . .
C12 C 0.0212(2) 0.34430(18) 0.35117(13) 0.0271(4) Uani 1 1 d . . .
H12 H -0.0743 0.2832 0.3331 0.032 Uiso 1 1 calc R . .
C13 C 0.0801(2) 0.4386(2) 0.27682(13) 0.0328(4) Uani 1 1 d . . .
H13 H 0.0241 0.4402 0.2095 0.039 Uiso 1 1 calc R . .
C22 C 0.3386(2) -0.5890(2) 0.82121(14) 0.0329(4) Uani 1 1 d . . .
H22 H 0.3658 -0.6463 0.7633 0.039 Uiso 1 1 calc R . .
C21 C 0.2355(2) -0.65218(19) 0.88929(14) 0.0304(4) Uani 1 1 d . . .
H21 H 0.1923 -0.7516 0.8768 0.036 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0181(6) 0.0246(6) 0.0267(6) 0.0066(5) 0.0015(4) 0.0029(4)
O2 0.0248(6) 0.0309(6) 0.0268(6) 0.0109(5) 0.0068(5) 0.0105(5)
O1 0.0283(7) 0.0278(7) 0.0437(8) 0.0029(5) 0.0119(5) -0.0033(5)
C2 0.0207(8) 0.0240(8) 0.0233(8) 0.0004(7) 0.0011(6) 0.0054(6)
C3 0.0257(9) 0.0171(8) 0.0206(8) 0.0009(6) 0.0042(6) 0.0018(6)
C5 0.0193(8) 0.0145(8) 0.0253(9) -0.0010(6) -0.0005(6) 0.0001(6)
C6 0.0242(8) 0.0200(8) 0.0201(8) 0.0009(6) 0.0024(6) 0.0005(6)
C4 0.0214(8) 0.0179(8) 0.0225(8) -0.0002(6) 0.0047(6) 0.0020(6)
C8 0.0223(8) 0.0239(9) 0.0213(8) 0.0060(6) 0.0014(6) 0.0039(7)
C1 0.0207(8) 0.0202(8) 0.0244(8) -0.0030(6) 0.0022(6) -0.0006(6)
C17 0.0231(8) 0.0242(9) 0.0231(9) 0.0049(7) 0.0001(6) 0.0027(7)
C18 0.0194(8) 0.0220(8) 0.0233(8) 0.0044(6) -0.0008(6) 0.0044(6)
C10 0.0215(8) 0.0273(9) 0.0264(9) 0.0044(7) 0.0019(7) 0.0075(7)
C20 0.0275(9) 0.0275(9) 0.0352(10) 0.0091(7) 0.0061(7) 0.0005(7)
C15 0.0231(9) 0.0299(9) 0.0416(11) 0.0064(8) 0.0054(8) 0.0034(7)
C16 0.0244(9) 0.0321(9) 0.0287(9) 0.0045(7) -0.0005(7) 0.0059(7)
C11 0.0216(8) 0.0210(8) 0.0262(9) 0.0024(6) 0.0043(7) 0.0078(6)
C7 0.0235(9) 0.0373(10) 0.0301(9) 0.0043(7) 0.0053(7) 0.0041(7)
C23 0.0319(9) 0.0262(9) 0.0302(9) 0.0038(7) 0.0078(7) 0.0047(7)
C9 0.0335(9) 0.0303(10) 0.0346(10) 0.0028(7) 0.0117(8) 0.0064(7)
C14 0.0355(10) 0.0295(9) 0.0360(10) 0.0105(8) 0.0143(8) 0.0105(8)
C19 0.0286(9) 0.0264(9) 0.0259(9) 0.0029(7) 0.0052(7) 0.0048(7)
C12 0.0303(9) 0.0241(9) 0.0265(9) -0.0018(7) 0.0010(7) 0.0038(7)
C13 0.0440(11) 0.0330(10) 0.0219(9) 0.0022(7) 0.0020(8) 0.0112(8)
C22 0.0415(10) 0.0274(9) 0.0296(9) -0.0015(7) 0.0016(8) 0.0069(8)
C21 0.0307(9) 0.0210(8) 0.0374(10) 0.0027(7) -0.0072(8) 0.0018(7)

_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
O3 C5 1.3758(18) . ?
O3 C17 1.4394(18) . ?
O2 C3 1.3671(18) . ?
O2 C10 1.4443(18) . ?
O1 C8 1.2116(19) . ?
C2 C3 1.390(2) . ?
C2 C1 1.393(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(2) . ?
C5 C6 1.388(2) . ?
C5 C4 1.391(2) . ?
C6 C1 1.394(2) . ?
C6 H6 0.9300 . ?
C4 C8 1.512(2) . ?
C8 C9 1.496(2) . ?
C1 C7 1.504(2) . ?
C17 C18 1.509(2) . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C18 C19 1.386(2) . ?
C18 C23 1.390(2) . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C20 C21 1.381(2) . ?
C20 C19 1.384(2) . ?
C20 H20 0.9300 . ?
C15 C16 1.387(2) . ?
C15 C14 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C11 1.390(2) . ?
C16 H16 0.9300 . ?
C11 C12 1.384(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C23 C22 1.383(2) . ?
C23 H23 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C14 C13 1.381(3) . ?
C14 H14 0.9300 . ?
C19 H19 0.9300 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C22 C21 1.384(3) . ?
C22 H22 0.9300 . ?
C21 H21 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 O3 C17 118.32(12) . . ?
C3 O2 C10 117.52(12) . . ?
C3 C2 C1 119.88(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O2 C3 C2 124.65(14) . . ?
O2 C3 C4 114.83(13) . . ?
C2 C3 C4 120.51(14) . . ?
O3 C5 C6 124.68(14) . . ?
O3 C5 C4 114.11(13) . . ?
C6 C5 C4 121.18(14) . . ?
C5 C6 C1 119.47(14) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C4 C3 118.79(14) . . ?
C5 C4 C8 119.97(13) . . ?
C3 C4 C8 121.24(14) . . ?
O1 C8 C9 122.63(14) . . ?
O1 C8 C4 121.45(14) . . ?
C9 C8 C4 115.91(14) . . ?
C2 C1 C6 120.12(14) . . ?
C2 C1 C7 120.23(14) . . ?
C6 C1 C7 119.61(14) . . ?
O3 C17 C18 112.99(12) . . ?
O3 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
O3 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
H17B C17 H17A 107.8 . . ?
C19 C18 C23 118.64(15) . . ?
C19 C18 C17 120.96(14) . . ?
C23 C18 C17 120.36(14) . . ?
O2 C10 C11 108.16(12) . . ?
O2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C21 C20 C19 120.07(16) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C16 C15 C14 120.02(17) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.74(16) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C12 C11 C16 118.67(15) . . ?
C12 C11 C10 120.78(15) . . ?
C16 C11 C10 120.52(15) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C22 C23 C18 120.76(16) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C14 C15 119.67(16) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C20 C19 C18 120.77(16) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C11 C12 C13 120.87(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.03(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C21 C22 C23 119.99(16) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C20 C21 C22 119.76(16) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?

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
C10 O2 C3 C2 14.6(2) . . . . ?
C10 O2 C3 C4 -166.38(13) . . . . ?
C1 C2 C3 O2 179.02(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C17 O3 C5 C6 6.5(2) . . . . ?
C17 O3 C5 C4 -175.67(13) . . . . ?
O3 C5 C6 C1 177.28(13) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
O3 C5 C4 C3 -175.76(12) . . . . ?
C6 C5 C4 C3 2.2(2) . . . . ?
O3 C5 C4 C8 4.5(2) . . . . ?
C6 C5 C4 C8 -177.60(14) . . . . ?
O2 C3 C4 C5 178.95(13) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
O2 C3 C4 C8 -1.3(2) . . . . ?
C2 C3 C4 C8 177.79(14) . . . . ?
C5 C4 C8 O1 -105.09(18) . . . . ?
C3 C4 C8 O1 75.1(2) . . . . ?
C5 C4 C8 C9 76.15(19) . . . . ?
C3 C4 C8 C9 -103.61(18) . . . . ?
C3 C2 C1 C6 1.8(2) . . . . ?
C3 C2 C1 C7 -176.11(14) . . . . ?
C5 C6 C1 C2 -1.6(2) . . . . ?
C5 C6 C1 C7 176.31(14) . . . . ?
C5 O3 C17 C18 71.70(17) . . . . ?
O3 C17 C18 C19 -138.10(15) . . . . ?
O3 C17 C18 C23 44.2(2) . . . . ?
C3 O2 C10 C11 164.76(13) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C15 C16 C11 C12 -0.8(2) . . . . ?
C15 C16 C11 C10 -178.65(14) . . . . ?
O2 C10 C11 C12 126.75(15) . . . . ?
O2 C10 C11 C16 -55.48(19) . . . . ?
C19 C18 C23 C22 0.4(2) . . . . ?
C17 C18 C23 C22 178.13(14) . . . . ?
C16 C15 C14 C13 0.6(3) . . . . ?
C21 C20 C19 C18 -1.0(2) . . . . ?
C23 C18 C19 C20 0.2(2) . . . . ?
C17 C18 C19 C20 -177.56(14) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C12 C13 178.62(14) . . . . ?
C15 C14 C13 C12 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C18 C23 C22 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 1.2(2) . . . . ?
C23 C22 C21 C20 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056

# Attachment 'Compound-4.cif'

data_a-11
_database_code_depnum_ccdc_archive 'CCDC 824675'
#TrackingRef 'Compound-4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.44

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   31.128(6)
_cell_length_b                   8.2169(16)
_cell_length_c                   17.034(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4357.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1930
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39072
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3841
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0573P)^2^+0.7929P] where P=(Fo^2^+2Fc^2^)/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       0.0037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O3 O 1.15238(5) 0.69002(16) 0.64740(8) 0.0617(4) Uani 1 1 d . . .
O4 O 1.03808(5) 0.34589(19) 0.57794(9) 0.0762(5) Uani 1 1 d . . .
C4 C 1.09464(7) 0.5160(2) 0.61061(11) 0.0549(5) Uani 1 1 d . . .
C24 C 0.90550(9) 0.1444(4) 0.5935(2) 0.1000(9) Uani 1 1 d . . .
H24 H 0.8780 0.1793 0.5805 0.120 Uiso 1 1 calc R . .
C3 C 1.13512(7) 0.5775(2) 0.59515(12) 0.0565(5) Uani 1 1 d . . .
C12 C 1.14637(8) 0.8566(3) 0.62367(13) 0.0688(6) Uani 1 1 d . . .
H12A H 1.1159 0.8802 0.6200 0.083 Uiso 1 1 calc R . .
H12B H 1.1591 0.8734 0.5723 0.083 Uiso 1 1 calc R . .
C9 C 1.23811(9) 0.5390(4) 0.57522(19) 0.1142(11) Uani 1 1 d . . .
H9A H 1.2647 0.5900 0.5609 0.171 Uiso 1 1 calc R . .
H9B H 1.2413 0.4229 0.5728 0.171 Uiso 1 1 calc R . .
H9C H 1.2304 0.5705 0.6276 0.171 Uiso 1 1 calc R . .
C20 C 0.98095(7) 0.1559(3) 0.57270(12) 0.0625(6) Uani 1 1 d . . .
O2 O 1.05182(7) 0.7065(2) 0.67588(12) 0.1105(7) Uani 1 1 d . . .
C13 C 1.16685(6) 0.9690(2) 0.68178(11) 0.0553(5) Uani 1 1 d . . .
C14 C 1.19316(7) 0.9141(3) 0.74072(13) 0.0634(6) Uani 1 1 d . . .
H14 H 1.1989 0.8034 0.7453 0.076 Uiso 1 1 calc R . .
C18 C 1.15971(8) 1.1348(3) 0.67505(14) 0.0734(7) Uani 1 1 d . . .
H18 H 1.1422 1.1738 0.6350 0.088 Uiso 1 1 calc R . .
C1 C 1.14204(8) 0.4126(3) 0.47989(13) 0.0692(6) Uani 1 1 d . . .
C10 C 1.06857(7) 0.5756(3) 0.67903(13) 0.0664(6) Uani 1 1 d . . .
C21 C 0.98626(9) 0.0435(3) 0.63043(14) 0.0806(7) Uani 1 1 d . . .
H21 H 1.0138 0.0084 0.6433 0.097 Uiso 1 1 calc R . .
C25 C 0.94019(9) 0.2055(3) 0.55450(15) 0.0825(7) Uani 1 1 d . . .
H25 H 0.9361 0.2819 0.5149 0.099 Uiso 1 1 calc R . .
C17 C 1.17817(9) 1.2428(3) 0.72692(16) 0.0838(8) Uani 1 1 d . . .
H17 H 1.1732 1.3538 0.7215 0.101 Uiso 1 1 calc R . .
C22 C 0.95165(14) -0.0187(3) 0.66988(16) 0.1000(9) Uani 1 1 d . . .
H22 H 0.9557 -0.0957 0.7092 0.120 Uiso 1 1 calc R . .
C2 C 1.15961(7) 0.5263(3) 0.53149(12) 0.0606(6) Uani 1 1 d . . .
C5 C 1.07804(7) 0.3998(3) 0.55877(12) 0.0614(6) Uani 1 1 d . . .
C15 C 1.21119(8) 1.0226(3) 0.79342(14) 0.0774(7) Uani 1 1 d . . .
H15 H 1.2285 0.9844 0.8339 0.093 Uiso 1 1 calc R . .
O1 O 1.21237(7) 0.6831(3) 0.46878(13) 0.1403(10) Uani 1 1 d . . .
C6 C 1.10143(8) 0.3510(3) 0.49385(13) 0.0708(7) Uani 1 1 d . . .
H6 H 1.0897 0.2757 0.4592 0.085 Uiso 1 1 calc R . .
C23 C 0.91113(12) 0.0329(5) 0.65123(19) 0.1030(10) Uani 1 1 d . . .
H23 H 0.8875 -0.0084 0.6781 0.124 Uiso 1 1 calc R . .
C16 C 1.20355(8) 1.1874(3) 0.78600(16) 0.0817(7) Uani 1 1 d . . .
H16 H 1.2157 1.2602 0.8214 0.098 Uiso 1 1 calc R . .
C8 C 1.20408(8) 0.5906(3) 0.52027(15) 0.0735(7) Uani 1 1 d . . .
C11 C 1.06477(10) 0.4694(4) 0.74865(16) 0.1096(10) Uani 1 1 d . . .
H11A H 1.0459 0.5189 0.7862 0.164 Uiso 1 1 calc R . .
H11B H 1.0926 0.4544 0.7718 0.164 Uiso 1 1 calc R . .
H11C H 1.0534 0.3657 0.7332 0.164 Uiso 1 1 calc R . .
C19 C 1.01901(8) 0.2215(3) 0.52944(15) 0.0881(8) Uani 1 1 d . . .
H19A H 1.0396 0.1353 0.5195 0.106 Uiso 1 1 calc R . .
H19B H 1.0101 0.2672 0.4795 0.106 Uiso 1 1 calc R . .
C7 C 1.16704(9) 0.3523(4) 0.40867(16) 0.1055(10) Uani 1 1 d . . .
H7A H 1.1528 0.2594 0.3866 0.158 Uiso 1 1 calc R . .
H7B H 1.1956 0.3222 0.4244 0.158 Uiso 1 1 calc R . .
H7C H 1.1686 0.4372 0.3701 0.158 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0730(10) 0.0522(9) 0.0599(8) -0.0015(7) -0.0140(7) -0.0051(7)
O4 0.0734(10) 0.0737(10) 0.0814(10) -0.0263(9) 0.0104(8) -0.0218(8)
C4 0.0620(13) 0.0482(12) 0.0545(12) -0.0028(10) -0.0011(10) -0.0005(10)
C24 0.0679(18) 0.125(3) 0.107(2) -0.021(2) -0.0040(17) 0.0012(18)
C3 0.0652(14) 0.0504(12) 0.0540(12) -0.0004(10) -0.0085(11) -0.0041(10)
C12 0.0805(16) 0.0558(14) 0.0700(14) 0.0058(11) -0.0151(12) -0.0052(12)
C9 0.0696(17) 0.114(2) 0.159(3) 0.027(2) -0.0208(19) 0.0025(16)
C20 0.0676(15) 0.0579(13) 0.0619(13) -0.0079(11) -0.0067(11) -0.0118(11)
O2 0.1392(17) 0.0810(13) 0.1112(15) -0.0105(12) 0.0326(13) 0.0304(12)
C13 0.0551(12) 0.0539(13) 0.0571(12) 0.0029(10) 0.0038(10) -0.0050(10)
C14 0.0630(14) 0.0584(13) 0.0688(14) -0.0047(11) -0.0051(12) -0.0032(11)
C18 0.0809(16) 0.0625(15) 0.0768(15) 0.0040(13) -0.0006(13) -0.0001(13)
C1 0.0741(16) 0.0709(15) 0.0627(13) -0.0099(12) 0.0062(12) -0.0055(12)
C10 0.0684(14) 0.0633(15) 0.0675(14) -0.0096(12) 0.0008(12) -0.0060(12)
C21 0.0870(18) 0.0767(17) 0.0781(17) 0.0044(15) -0.0194(14) -0.0011(14)
C25 0.095(2) 0.0760(17) 0.0767(16) 0.0064(14) -0.0162(15) 0.0017(15)
C17 0.105(2) 0.0553(15) 0.0912(19) -0.0093(14) 0.0079(16) -0.0073(14)
C22 0.149(3) 0.0830(19) 0.0680(17) 0.0143(15) -0.0059(19) -0.032(2)
C2 0.0612(13) 0.0625(14) 0.0582(13) -0.0002(11) -0.0021(11) -0.0034(11)
C5 0.0653(14) 0.0537(13) 0.0653(14) -0.0060(11) 0.0025(12) -0.0073(11)
C15 0.0736(15) 0.0832(18) 0.0755(16) -0.0102(14) -0.0146(13) -0.0090(14)
O1 0.1004(15) 0.213(3) 0.1076(15) 0.0670(17) -0.0133(12) -0.0604(16)
C6 0.0772(16) 0.0682(15) 0.0668(14) -0.0208(12) 0.0027(12) -0.0132(13)
C23 0.100(2) 0.125(3) 0.084(2) -0.029(2) 0.0232(18) -0.050(2)
C16 0.0861(18) 0.0745(18) 0.0845(18) -0.0220(15) 0.0062(15) -0.0206(14)
C8 0.0702(16) 0.0814(17) 0.0689(15) -0.0012(13) 0.0008(13) -0.0085(13)
C11 0.122(2) 0.132(3) 0.0753(17) 0.0125(18) 0.0230(17) 0.010(2)
C19 0.0943(19) 0.0888(18) 0.0812(17) -0.0241(15) 0.0047(14) -0.0393(15)
C7 0.100(2) 0.128(2) 0.0880(18) -0.0388(18) 0.0287(16) -0.0179(18)

_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
O3 C3 1.391(2) . ?
O3 C12 1.439(2) . ?
O4 C5 1.360(2) . ?
O4 C19 1.442(3) . ?
C4 C3 1.383(3) . ?
C4 C5 1.399(3) . ?
C4 C10 1.502(3) . ?
C24 C23 1.355(4) . ?
C24 C25 1.364(4) . ?
C24 H24 0.9300 . ?
C3 C2 1.391(3) . ?
C12 C13 1.496(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C8 1.476(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 C21 1.359(3) . ?
C20 C25 1.368(3) . ?
C20 C19 1.496(3) . ?
O2 C10 1.197(3) . ?
C13 C14 1.372(3) . ?
C13 C18 1.386(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C18 C17 1.377(3) . ?
C18 H18 0.9300 . ?
C1 C6 1.382(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.524(3) . ?
C10 C11 1.477(3) . ?
C21 C22 1.369(4) . ?
C21 H21 0.9300 . ?
C25 H25 0.9300 . ?
C17 C16 1.358(4) . ?
C17 H17 0.9300 . ?
C22 C23 1.368(4) . ?
C22 H22 0.9300 . ?
C2 C8 1.494(3) . ?
C5 C6 1.384(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
O1 C8 1.189(3) . ?
C6 H6 0.9300 . ?
C23 H23 0.9300 . ?
C16 H16 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 C12 113.71(15) . . ?
C5 O4 C19 118.03(17) . . ?
C3 C4 C5 117.76(19) . . ?
C3 C4 C10 121.38(18) . . ?
C5 C4 C10 120.82(19) . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C4 C3 C2 122.49(19) . . ?
C4 C3 O3 118.24(18) . . ?
C2 C3 O3 119.23(19) . . ?
O3 C12 C13 110.22(16) . . ?
O3 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O3 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C21 C20 C25 118.6(2) . . ?
C21 C20 C19 120.3(2) . . ?
C25 C20 C19 121.0(2) . . ?
C14 C13 C18 118.7(2) . . ?
C14 C13 C12 122.38(19) . . ?
C18 C13 C12 119.0(2) . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 C7 119.0(2) . . ?
C2 C1 C7 121.3(2) . . ?
O2 C10 C11 122.2(2) . . ?
O2 C10 C4 119.6(2) . . ?
C11 C10 C4 118.2(2) . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C24 C25 C20 120.9(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C8 120.02(19) . . ?
C1 C2 C8 121.3(2) . . ?
O4 C5 C6 125.35(19) . . ?
O4 C5 C4 114.12(18) . . ?
C6 C5 C4 120.5(2) . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O1 C8 C9 119.7(2) . . ?
O1 C8 C2 121.5(2) . . ?
C9 C8 C2 118.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C19 C20 107.42(18) . . ?
O4 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O4 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C5 C4 C3 C2 -1.1(3) . . . . ?
C10 C4 C3 C2 -178.9(2) . . . . ?
C5 C4 C3 O3 -178.42(17) . . . . ?
C10 C4 C3 O3 3.7(3) . . . . ?
C12 O3 C3 C4 -96.6(2) . . . . ?
C12 O3 C3 C2 86.0(2) . . . . ?
C3 O3 C12 C13 -178.47(17) . . . . ?
O3 C12 C13 C14 9.8(3) . . . . ?
O3 C12 C13 C18 -171.50(19) . . . . ?
C18 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 C15 -179.6(2) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
C12 C13 C18 C17 -179.5(2) . . . . ?
C3 C4 C10 O2 74.6(3) . . . . ?
C5 C4 C10 O2 -103.2(3) . . . . ?
C3 C4 C10 C11 -105.1(3) . . . . ?
C5 C4 C10 C11 77.1(3) . . . . ?
C25 C20 C21 C22 -0.2(4) . . . . ?
C19 C20 C21 C22 -179.3(2) . . . . ?
C23 C24 C25 C20 0.0(4) . . . . ?
C21 C20 C25 C24 0.3(4) . . . . ?
C19 C20 C25 C24 179.4(2) . . . . ?
C13 C18 C17 C16 -0.4(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C4 C3 C2 C1 2.2(3) . . . . ?
O3 C3 C2 C1 179.56(18) . . . . ?
C4 C3 C2 C8 -176.7(2) . . . . ?
O3 C3 C2 C8 0.6(3) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 C1 C2 C3 179.6(2) . . . . ?
C6 C1 C2 C8 177.5(2) . . . . ?
C7 C1 C2 C8 -1.5(4) . . . . ?
C19 O4 C5 C6 3.4(3) . . . . ?
C19 O4 C5 C4 -177.8(2) . . . . ?
C3 C4 C5 O4 -179.80(18) . . . . ?
C10 C4 C5 O4 -1.9(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C10 C4 C5 C6 177.0(2) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C7 C1 C6 C5 178.6(2) . . . . ?
O4 C5 C6 C1 -179.6(2) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C25 C24 C23 C22 -0.3(5) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C18 C17 C16 C15 0.7(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C3 C2 C8 O1 -108.9(3) . . . . ?
C1 C2 C8 O1 72.2(3) . . . . ?
C3 C2 C8 C9 70.4(3) . . . . ?
C1 C2 C8 C9 -108.5(3) . . . . ?
C5 O4 C19 C20 166.6(2) . . . . ?
C21 C20 C19 O4 -80.6(3) . . . . ?
C25 C20 C19 O4 100.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.031