# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Zofia Urbanczyk-Lipkowska'
_publ_contact_author_email       ocryst@icho.edu.pl
loop_
_publ_author_name
Z.Urbanczyk-Lipkowska
P.Kalicki
'Sylwester Gawinkowski'
'Jacek Waluk'
'Masashi Yokoyama'
K.Tanaka

# Attachment '1b_orange.cif'

data_tana1_orange_0ma
_database_code_depnum_ccdc_archive 'CCDC 751997'
#TrackingRef '1b_orange.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'orange polymorph'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 O4'
_chemical_formula_weight         368.37

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9787(2)
_cell_length_b                   8.0272(2)
_cell_length_c                   15.4271(5)
_cell_angle_alpha                92.228(2)
_cell_angle_beta                 97.055(2)
_cell_angle_gamma                119.4050(10)
_cell_volume                     848.61(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4544
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8316
_exptl_absorpt_correction_T_max  0.9104
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9547
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         65.05
_reflns_number_total             2832
_reflns_number_gt                2472
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0435P)^2^+0.2295P] 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       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.9212(2) 0.2773(2) 0.19585(10) 0.0352(3) Uani 1 1 d . . .
C2 C 1.0131(2) 0.4044(2) 0.28187(9) 0.0371(4) Uani 1 1 d . . .
H2A H 0.9279 0.4509 0.2974 0.045 Uiso 1 1 calc R . .
H2B H 1.1352 0.5153 0.2742 0.045 Uiso 1 1 calc R . .
C3 C 1.0530(2) 0.3049(2) 0.35813(10) 0.0404(4) Uani 1 1 d . . .
H3A H 1.1693 0.2978 0.3530 0.049 Uiso 1 1 calc R . .
H3B H 1.0772 0.3815 0.4133 0.049 Uiso 1 1 calc R . .
C4 C 0.8863(2) 0.1066(2) 0.35932(10) 0.0353(3) Uani 1 1 d . . .
C5 C 0.8080(2) -0.0159(2) 0.27225(10) 0.0417(4) Uani 1 1 d . . .
H5A H 0.6702 -0.0586 0.2574 0.050 Uiso 1 1 calc R . .
H5B H 0.8207 -0.1294 0.2777 0.050 Uiso 1 1 calc R . .
C6 C 0.9104(3) 0.0865(2) 0.19751(10) 0.0431(4) Uani 1 1 d . . .
H6A H 1.0411 0.1047 0.2052 0.052 Uiso 1 1 calc R . .
H6B H 0.8397 0.0079 0.1419 0.052 Uiso 1 1 calc R . .
C7 C 0.8541(2) 0.3320(2) 0.12394(10) 0.0352(3) Uani 1 1 d . . .
C8 C 0.7655(2) 0.2227(2) 0.03459(10) 0.0356(3) Uani 1 1 d . . .
C9 C 0.7203(2) 0.3480(2) -0.02078(9) 0.0341(3) Uani 1 1 d . . .
C10 C 0.6345(2) 0.3115(2) -0.10784(10) 0.0423(4) Uani 1 1 d . . .
H10A H 0.5970 0.1958 -0.1409 0.051 Uiso 1 1 calc R . .
C11 C 0.6060(2) 0.4520(2) -0.14462(11) 0.0460(4) Uani 1 1 d . . .
H11A H 0.5474 0.4303 -0.2030 0.055 Uiso 1 1 calc R . .
C12 C 0.6640(2) 0.6251(2) -0.09500(10) 0.0448(4) Uani 1 1 d . . .
H12 H 0.6433 0.7175 -0.1209 0.054 Uiso 1 1 calc R . .
C13 C 0.7515(2) 0.6630(2) -0.00854(10) 0.0411(4) Uani 1 1 d . . .
H13 H 0.7920 0.7799 0.0241 0.049 Uiso 1 1 calc R . .
C14 C 0.7773(2) 0.5206(2) 0.02820(9) 0.0344(3) Uani 1 1 d . . .
C15 C 0.8606(2) 0.5199(2) 0.11952(10) 0.0375(4) Uani 1 1 d . . .
C16 C 0.8080(2) 0.0387(2) 0.43193(10) 0.0352(3) Uani 1 1 d . . .
C17 C 0.6363(2) -0.1548(2) 0.43449(10) 0.0372(4) Uani 1 1 d . . .
C18 C 0.5993(2) -0.1665(2) 0.52685(10) 0.0366(3) Uani 1 1 d . . .
C19 C 0.4606(2) -0.3186(2) 0.56349(11) 0.0451(4) Uani 1 1 d . . .
H19 H 0.3710 -0.4336 0.5292 0.054 Uiso 1 1 calc R . .
C20 C 0.4593(3) -0.2945(3) 0.65246(12) 0.0501(4) Uani 1 1 d . . .
H20 H 0.3690 -0.3955 0.6788 0.060 Uiso 1 1 calc R . .
C21 C 0.5914(3) -0.1210(3) 0.70311(11) 0.0499(4) Uani 1 1 d . . .
H21 H 0.5859 -0.1069 0.7626 0.060 Uiso 1 1 calc R . .
C22 C 0.7309(3) 0.0310(2) 0.66686(10) 0.0442(4) Uani 1 1 d . . .
H22 H 0.8195 0.1466 0.7010 0.053 Uiso 1 1 calc R . .
C23 C 0.7339(2) 0.0051(2) 0.57787(10) 0.0363(3) Uani 1 1 d . . .
C24 C 0.8711(2) 0.1393(2) 0.52309(10) 0.0373(4) Uani 1 1 d . . .
O1 O 0.73525(18) 0.06413(16) 0.00825(7) 0.0520(3) Uani 1 1 d . . .
O2 O 0.9200(2) 0.65035(17) 0.17830(8) 0.0591(4) Uani 1 1 d . . .
O3 O 0.53957(18) -0.28164(16) 0.37390(7) 0.0536(3) Uani 1 1 d . . .
O4 O 1.00937(19) 0.29776(16) 0.55076(8) 0.0572(4) Uani 1 1 d . . .

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
C1 0.0379(8) 0.0338(8) 0.0363(8) 0.0037(6) 0.0066(6) 0.0196(7)
C2 0.0405(8) 0.0355(8) 0.0352(8) 0.0048(6) 0.0045(6) 0.0194(7)
C3 0.0384(8) 0.0362(9) 0.0380(8) 0.0055(7) -0.0002(7) 0.0134(7)
C4 0.0372(8) 0.0321(8) 0.0361(8) 0.0023(6) -0.0021(6) 0.0188(7)
C5 0.0523(9) 0.0356(9) 0.0363(8) 0.0014(7) 0.0016(7) 0.0226(8)
C6 0.0606(10) 0.0427(9) 0.0358(8) 0.0038(7) 0.0060(7) 0.0337(8)
C7 0.0390(8) 0.0306(8) 0.0361(8) 0.0001(6) 0.0016(6) 0.0186(7)
C8 0.0378(8) 0.0292(8) 0.0387(8) 0.0001(6) 0.0038(6) 0.0168(6)
C9 0.0339(7) 0.0318(8) 0.0347(8) -0.0001(6) 0.0020(6) 0.0161(6)
C10 0.0454(9) 0.0404(9) 0.0362(8) -0.0033(7) -0.0005(7) 0.0200(7)
C11 0.0471(9) 0.0528(10) 0.0357(8) 0.0054(7) -0.0002(7) 0.0247(8)
C12 0.0495(9) 0.0472(10) 0.0437(9) 0.0152(8) 0.0070(7) 0.0282(8)
C13 0.0499(9) 0.0355(8) 0.0424(9) 0.0043(7) 0.0059(7) 0.0251(8)
C14 0.0356(8) 0.0331(8) 0.0353(8) 0.0018(6) 0.0039(6) 0.0183(6)
C15 0.0436(8) 0.0342(8) 0.0344(8) -0.0020(7) -0.0007(6) 0.0213(7)
C16 0.0376(8) 0.0285(8) 0.0352(8) 0.0024(6) -0.0014(6) 0.0149(7)
C17 0.0396(8) 0.0290(8) 0.0376(8) 0.0005(6) -0.0029(7) 0.0153(7)
C18 0.0338(8) 0.0324(8) 0.0418(8) 0.0052(6) 0.0004(6) 0.0164(7)
C19 0.0353(8) 0.0383(9) 0.0556(10) 0.0080(8) 0.0032(7) 0.0146(7)
C20 0.0451(9) 0.0527(11) 0.0605(11) 0.0223(9) 0.0183(8) 0.0272(9)
C21 0.0616(11) 0.0606(12) 0.0443(9) 0.0158(8) 0.0162(8) 0.0409(10)
C22 0.0554(10) 0.0411(9) 0.0394(9) 0.0027(7) 0.0014(7) 0.0280(8)
C23 0.0398(8) 0.0327(8) 0.0367(8) 0.0043(6) 0.0007(6) 0.0195(7)
C24 0.0407(8) 0.0285(8) 0.0361(8) 0.0013(6) -0.0023(6) 0.0142(7)
O1 0.0714(8) 0.0357(7) 0.0488(7) -0.0060(5) -0.0057(6) 0.0310(6)
O2 0.0929(10) 0.0449(7) 0.0427(7) -0.0118(6) -0.0139(6) 0.0434(7)
O3 0.0582(7) 0.0347(6) 0.0436(7) -0.0048(5) -0.0045(6) 0.0082(6)
O4 0.0619(8) 0.0354(7) 0.0421(7) -0.0032(5) -0.0008(6) 0.0025(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
C1 C7 1.354(2) . ?
C1 C6 1.493(2) . ?
C1 C2 1.504(2) . ?
C2 C3 1.534(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.494(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C16 1.352(2) . ?
C4 C5 1.500(2) . ?
C5 C6 1.523(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C15 1.488(2) . ?
C7 C8 1.492(2) . ?
C8 O1 1.2158(18) . ?
C8 C9 1.489(2) . ?
C9 C10 1.380(2) . ?
C9 C14 1.383(2) . ?
C10 C11 1.384(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.484(2) . ?
C15 O2 1.2151(18) . ?
C16 C17 1.490(2) . ?
C16 C24 1.491(2) . ?
C17 O3 1.2180(18) . ?
C17 C18 1.487(2) . ?
C18 C19 1.384(2) . ?
C18 C23 1.388(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.488(2) . ?
C24 O4 1.2170(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C6 123.49(14) . . ?
C7 C1 C2 122.67(13) . . ?
C6 C1 C2 113.84(12) . . ?
C1 C2 C3 114.18(12) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 112.08(12) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C16 C4 C3 123.99(14) . . ?
C16 C4 C5 121.20(14) . . ?
C3 C4 C5 114.81(13) . . ?
C4 C5 C6 113.81(13) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C1 C6 C5 110.45(12) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C1 C7 C15 125.28(13) . . ?
C1 C7 C8 128.00(13) . . ?
C15 C7 C8 106.70(12) . . ?
O1 C8 C9 124.36(14) . . ?
O1 C8 C7 129.05(14) . . ?
C9 C8 C7 106.58(12) . . ?
C10 C9 C14 120.93(14) . . ?
C10 C9 C8 129.14(14) . . ?
C14 C9 C8 109.93(12) . . ?
C9 C10 C11 118.14(15) . . ?
C9 C10 H10A 120.9 . . ?
C11 C10 H10A 120.9 . . ?
C10 C11 C12 120.53(15) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 121.55(15) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 117.59(15) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C9 C14 C13 121.25(14) . . ?
C9 C14 C15 109.72(13) . . ?
C13 C14 C15 129.03(14) . . ?
O2 C15 C14 124.98(14) . . ?
O2 C15 C7 127.96(14) . . ?
C14 C15 C7 107.06(12) . . ?
C4 C16 C17 125.30(14) . . ?
C4 C16 C24 127.84(14) . . ?
C17 C16 C24 106.86(12) . . ?
O3 C17 C18 124.94(14) . . ?
O3 C17 C16 128.12(14) . . ?
C18 C17 C16 106.93(12) . . ?
C19 C18 C23 121.14(15) . . ?
C19 C18 C17 129.25(14) . . ?
C23 C18 C17 109.58(13) . . ?
C20 C19 C18 118.06(16) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 120.71(16) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 121.41(16) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 117.66(16) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 C18 120.98(15) . . ?
C22 C23 C24 129.08(14) . . ?
C18 C23 C24 109.93(13) . . ?
O4 C24 C23 124.71(14) . . ?
O4 C24 C16 128.59(14) . . ?
C23 C24 C16 106.68(12) . . ?

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
C7 C1 C2 C3 171.89(14) . . . . ?
C6 C1 C2 C3 -7.85(19) . . . . ?
C1 C2 C3 C4 -43.18(18) . . . . ?
C2 C3 C4 C16 -131.95(15) . . . . ?
C2 C3 C4 C5 47.73(18) . . . . ?
C16 C4 C5 C6 178.33(14) . . . . ?
C3 C4 C5 C6 -1.37(19) . . . . ?
C7 C1 C6 C5 -125.51(16) . . . . ?
C2 C1 C6 C5 54.23(18) . . . . ?
C4 C5 C6 C1 -49.79(18) . . . . ?
C6 C1 C7 C15 179.57(14) . . . . ?
C2 C1 C7 C15 -0.2(2) . . . . ?
C6 C1 C7 C8 -2.1(3) . . . . ?
C2 C1 C7 C8 178.17(14) . . . . ?
C1 C7 C8 O1 0.2(3) . . . . ?
C15 C7 C8 O1 178.74(16) . . . . ?
C1 C7 C8 C9 -178.89(15) . . . . ?
C15 C7 C8 C9 -0.32(16) . . . . ?
O1 C8 C9 C10 2.0(3) . . . . ?
C7 C8 C9 C10 -178.91(15) . . . . ?
O1 C8 C9 C14 -178.29(15) . . . . ?
C7 C8 C9 C14 0.83(16) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 C11 179.30(15) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 179.77(13) . . . . ?
C10 C9 C14 C15 178.76(14) . . . . ?
C8 C9 C14 C15 -1.00(17) . . . . ?
C12 C13 C14 C9 1.2(2) . . . . ?
C12 C13 C14 C15 -177.90(15) . . . . ?
C9 C14 C15 O2 -178.58(16) . . . . ?
C13 C14 C15 O2 0.6(3) . . . . ?
C9 C14 C15 C7 0.78(17) . . . . ?
C13 C14 C15 C7 179.93(15) . . . . ?
C1 C7 C15 O2 -2.3(3) . . . . ?
C8 C7 C15 O2 179.09(16) . . . . ?
C1 C7 C15 C14 178.37(14) . . . . ?
C8 C7 C15 C14 -0.25(16) . . . . ?
C3 C4 C16 C17 177.05(13) . . . . ?
C5 C4 C16 C17 -2.6(2) . . . . ?
C3 C4 C16 C24 -1.9(2) . . . . ?
C5 C4 C16 C24 178.40(14) . . . . ?
C4 C16 C17 O3 0.1(3) . . . . ?
C24 C16 C17 O3 179.22(15) . . . . ?
C4 C16 C17 C18 -179.01(14) . . . . ?
C24 C16 C17 C18 0.15(15) . . . . ?
O3 C17 C18 C19 3.3(3) . . . . ?
C16 C17 C18 C19 -177.63(15) . . . . ?
O3 C17 C18 C23 -178.38(15) . . . . ?
C16 C17 C18 C23 0.73(16) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C20 178.45(15) . . . . ?
C18 C19 C20 C21 1.2(2) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C18 1.1(2) . . . . ?
C21 C22 C23 C24 -177.23(15) . . . . ?
C19 C18 C23 C22 -1.4(2) . . . . ?
C17 C18 C23 C22 -179.91(13) . . . . ?
C19 C18 C23 C24 177.19(13) . . . . ?
C17 C18 C23 C24 -1.32(16) . . . . ?
C22 C23 C24 O4 1.5(3) . . . . ?
C18 C23 C24 O4 -176.96(15) . . . . ?
C22 C23 C24 C16 179.83(15) . . . . ?
C18 C23 C24 C16 1.39(16) . . . . ?
C4 C16 C24 O4 -3.5(3) . . . . ?
C17 C16 C24 O4 177.37(16) . . . . ?
C4 C16 C24 C23 178.23(14) . . . . ?
C17 C16 C24 C23 -0.90(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        65.05
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034


# Attachment '1a_yellow.cif'

data_tana1_yellow_0m
_database_code_depnum_ccdc_archive 'CCDC 751998'
#TrackingRef '1a_yellow.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'yellow polymorph'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 O4'
_chemical_formula_weight         368.37

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   C2

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                   7.9860(2)
_cell_length_b                   7.0973(2)
_cell_length_c                   15.2269(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1440(10)
_cell_angle_gamma                90.00
_cell_volume                     849.55(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5574
_cell_measurement_theta_min      5.90
_cell_measurement_theta_max      67.62

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8243
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6435
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.90
_diffrn_reflns_theta_max         67.88
_reflns_number_total             1476
_reflns_number_gt                1465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0363P)^2^+0.2238P] 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       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.56785(16) 0.22453(17) 0.41540(8) 0.0309(3) Uani 1 1 d . . .
C2 C 0.67061(16) 0.2998(2) 0.49963(8) 0.0333(3) Uani 1 1 d . . .
H2A H 0.6550 0.4352 0.5018 0.040 Uiso 1 1 calc R . .
H2B H 0.7902 0.2756 0.4997 0.040 Uiso 1 1 calc R . .
C3 C 0.38008(15) 0.21014(19) 0.41736(8) 0.0334(3) Uani 1 1 d . . .
H3A H 0.3477 0.0783 0.4150 0.040 Uiso 1 1 calc R . .
H3B H 0.3173 0.2712 0.3647 0.040 Uiso 1 1 calc R . .
C4 C 0.63414(15) 0.1719(2) 0.34349(8) 0.0329(3) Uani 1 1 d . . .
C5 C 0.81722(16) 0.1730(2) 0.33401(8) 0.0347(3) Uani 1 1 d . . .
C6 C 0.82553(16) 0.0981(2) 0.24386(8) 0.0365(3) Uani 1 1 d . . .
C7 C 0.96766(18) 0.0683(2) 0.20468(10) 0.0456(4) Uani 1 1 d . . .
H7 H 1.0763 0.0976 0.2346 0.055 Uiso 1 1 calc R . .
C8 C 0.9417(2) -0.0063(3) 0.11977(11) 0.0575(5) Uani 1 1 d . . .
H8 H 1.0344 -0.0261 0.0915 0.069 Uiso 1 1 calc R . .
C9 C 0.7784(2) -0.0526(3) 0.07531(11) 0.0620(5) Uani 1 1 d . . .
H9 H 0.7643 -0.1042 0.0183 0.074 Uiso 1 1 calc R . .
C10 C 0.6378(2) -0.0227(3) 0.11498(10) 0.0535(4) Uani 1 1 d . . .
H10 H 0.5291 -0.0530 0.0854 0.064 Uiso 1 1 calc R . .
C11 C 0.66330(17) 0.0534(2) 0.19975(9) 0.0382(3) Uani 1 1 d . . .
C12 C 0.53714(16) 0.0961(2) 0.25861(8) 0.0364(3) Uani 1 1 d . . .
O1 O 0.94073(12) 0.22056(17) 0.38823(7) 0.0494(3) Uani 1 1 d . . .
O2 O 0.38483(12) 0.07033(18) 0.23802(7) 0.0497(3) Uani 1 1 d . . .

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
C1 0.0265(6) 0.0384(6) 0.0284(6) 0.0039(5) 0.0062(5) 0.0004(5)
C2 0.0267(6) 0.0455(7) 0.0288(6) -0.0019(5) 0.0078(5) -0.0042(6)
C3 0.0258(6) 0.0472(7) 0.0284(6) -0.0013(5) 0.0084(5) -0.0021(5)
C4 0.0258(6) 0.0452(7) 0.0285(6) 0.0004(5) 0.0067(5) -0.0015(5)
C5 0.0276(6) 0.0480(7) 0.0292(6) 0.0019(5) 0.0071(5) 0.0003(5)
C6 0.0310(7) 0.0496(8) 0.0306(6) 0.0014(6) 0.0100(5) -0.0007(6)
C7 0.0340(7) 0.0639(9) 0.0422(7) 0.0007(7) 0.0155(6) 0.0005(7)
C8 0.0500(9) 0.0842(12) 0.0449(9) -0.0058(8) 0.0267(7) 0.0029(9)
C9 0.0584(10) 0.0958(14) 0.0359(8) -0.0171(8) 0.0199(7) -0.0071(10)
C10 0.0452(8) 0.0848(12) 0.0313(7) -0.0102(8) 0.0089(6) -0.0084(8)
C11 0.0339(7) 0.0540(8) 0.0281(6) 0.0007(6) 0.0090(5) -0.0005(6)
C12 0.0286(7) 0.0518(8) 0.0291(6) 0.0011(6) 0.0061(5) -0.0018(6)
O1 0.0278(5) 0.0825(8) 0.0377(5) -0.0097(5) 0.0051(4) -0.0066(5)
O2 0.0283(5) 0.0817(7) 0.0391(5) -0.0107(5) 0.0057(4) -0.0071(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
C1 C4 1.3501(18) . ?
C1 C2 1.4944(18) . ?
C1 C3 1.5085(16) . ?
C2 C3 1.5318(17) 2_656 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C2 1.5318(17) 2_656 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C12 1.4858(18) . ?
C4 C5 1.4943(17) . ?
C5 O1 1.2172(16) . ?
C5 C6 1.4845(18) . ?
C6 C11 1.3868(19) . ?
C6 C7 1.3883(18) . ?
C7 C8 1.379(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.4927(18) . ?
C12 O2 1.2153(16) . ?

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 C1 C2 124.09(11) . . ?
C4 C1 C3 122.04(11) . . ?
C2 C1 C3 113.87(11) . . ?
C1 C2 C3 112.01(11) . 2_656 ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 2_656 . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 2_656 . ?
H2A C2 H2B 107.9 . . ?
C1 C3 C2 113.35(11) . 2_656 ?
C1 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 2_656 . ?
C1 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 2_656 . ?
H3A C3 H3B 107.7 . . ?
C1 C4 C12 125.93(11) . . ?
C1 C4 C5 127.38(11) . . ?
C12 C4 C5 106.67(10) . . ?
O1 C5 C6 124.31(12) . . ?
O1 C5 C4 128.73(12) . . ?
C6 C5 C4 106.94(10) . . ?
C11 C6 C7 121.46(12) . . ?
C11 C6 C5 109.85(11) . . ?
C7 C6 C5 128.67(12) . . ?
C8 C7 C6 117.51(14) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C9 121.19(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 120.82(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 118.12(15) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C6 120.89(12) . . ?
C10 C11 C12 129.54(13) . . ?
C6 C11 C12 109.56(11) . . ?
O2 C12 C4 128.59(12) . . ?
O2 C12 C11 124.42(12) . . ?
C4 C12 C11 106.98(10) . . ?

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 -134.97(13) . . . 2_656 ?
C3 C1 C2 C3 44.55(14) . . . 2_656 ?
C4 C1 C3 C2 -172.81(12) . . . 2_656 ?
C2 C1 C3 C2 7.66(14) . . . 2_656 ?
C2 C1 C4 C12 179.85(13) . . . . ?
C3 C1 C4 C12 0.4(2) . . . . ?
C2 C1 C4 C5 1.7(2) . . . . ?
C3 C1 C4 C5 -177.83(13) . . . . ?
C1 C4 C5 O1 0.0(2) . . . . ?
C12 C4 C5 O1 -178.45(16) . . . . ?
C1 C4 C5 C6 178.51(13) . . . . ?
C12 C4 C5 C6 0.03(14) . . . . ?
O1 C5 C6 C11 178.63(15) . . . . ?
C4 C5 C6 C11 0.06(15) . . . . ?
O1 C5 C6 C7 0.0(2) . . . . ?
C4 C5 C6 C7 -178.61(15) . . . . ?
C11 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 178.97(16) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C10 C11 C12 -178.44(17) . . . . ?
C7 C6 C11 C10 0.1(2) . . . . ?
C5 C6 C11 C10 -178.70(15) . . . . ?
C7 C6 C11 C12 178.66(14) . . . . ?
C5 C6 C11 C12 -0.12(16) . . . . ?
C1 C4 C12 O2 1.1(2) . . . . ?
C5 C4 C12 O2 179.58(15) . . . . ?
C1 C4 C12 C11 -178.61(13) . . . . ?
C5 C4 C12 C11 -0.10(15) . . . . ?
C10 C11 C12 O2 -1.1(3) . . . . ?
C6 C11 C12 O2 -179.55(14) . . . . ?
C10 C11 C12 C4 178.56(17) . . . . ?
C6 C11 C12 C4 0.14(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        67.88
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.024

data_t1y_kond_2_b_0m
_database_code_depnum_ccdc_archive 'CCDC 786188'
#TrackingRef 'sublimation.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 O4'
_chemical_formula_sum            'C24 H14 O4'
_chemical_formula_weight         366.35

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.5043(7)
_cell_length_b                   7.8779(7)
_cell_length_c                   8.3841(7)
_cell_angle_alpha                83.864(6)
_cell_angle_beta                 79.848(7)
_cell_angle_gamma                61.879(6)
_cell_volume                     430.14(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    305
_cell_measurement_theta_min      5.36
_cell_measurement_theta_max      50.99

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             190
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5906
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker AXS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2857
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.36
_diffrn_reflns_theta_max         67.35
_reflns_number_total             1355
_reflns_number_gt                760
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0780P)^2^+0.0000P] 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       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1355
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C8 C 0.2278(5) 0.2347(5) 0.6512(4) 0.0400(9) Uani 1 1 d . . .
C4 C 0.2825(6) 0.3495(5) 0.3782(4) 0.0497(10) Uani 1 1 d . . .
H4 H 0.3050 0.4379 0.3060 0.060 Uiso 1 1 calc R . .
C3 C 0.2573(5) 0.3692(5) 0.5443(4) 0.0421(9) Uani 1 1 d . . .
C7 C 0.2165(6) 0.0810(5) 0.5966(4) 0.0492(10) Uani 1 1 d . . .
H7 H 0.1941 -0.0075 0.6687 0.059 Uiso 1 1 calc R . .
C5 C 0.2734(6) 0.1956(5) 0.3229(5) 0.0546(11) Uani 1 1 d . . .
H5 H 0.2901 0.1796 0.2120 0.066 Uiso 1 1 calc R . .
C6 C 0.2393(6) 0.0637(5) 0.4319(5) 0.0542(11) Uani 1 1 d . . .
H6 H 0.2319 -0.0383 0.3923 0.065 Uiso 1 1 calc R . .
C2 C 0.2589(6) 0.5178(6) 0.6351(5) 0.0471(10) Uani 1 1 d . . .
C1 C 0.2171(6) 0.4749(5) 0.8183(4) 0.0454(10) Uani 1 1 d . . .
H1 H 0.0789 0.5719 0.8590 0.054 Uiso 1 1 calc R . .
C9 C 0.2130(6) 0.2836(5) 0.8188(5) 0.0465(10) Uani 1 1 d . . .
O1 O 0.2826(4) 0.6550(4) 0.5786(3) 0.0616(9) Uani 1 1 d . . .
O2 O 0.1979(4) 0.1880(4) 0.9402(3) 0.0629(9) Uani 1 1 d . . .
C11 C 0.3199(6) 0.6605(5) 0.9742(4) 0.0487(10) Uani 1 1 d . . .
H11 H 0.1990 0.7697 0.9581 0.058 Uiso 1 1 calc R . .
C10 C 0.3612(6) 0.4856(5) 0.9159(4) 0.0434(10) Uani 1 1 d . . .
C12 C 0.4582(6) 0.6735(5) 1.0566(4) 0.0494(10) Uani 1 1 d . . .
H12 H 0.4284 0.7923 1.0941 0.059 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
C8 0.049(2) 0.047(2) 0.029(2) -0.0045(16) -0.0050(16) -0.0260(19)
C4 0.060(3) 0.055(2) 0.037(2) 0.0057(19) -0.0071(19) -0.031(2)
C3 0.051(2) 0.047(2) 0.034(2) 0.0011(17) -0.0082(17) -0.0265(19)
C7 0.064(3) 0.051(2) 0.041(2) 0.0012(18) -0.0118(19) -0.032(2)
C5 0.068(3) 0.063(3) 0.034(2) -0.0033(19) -0.0112(19) -0.031(2)
C6 0.069(3) 0.054(3) 0.046(3) -0.005(2) -0.015(2) -0.031(2)
C2 0.051(3) 0.045(2) 0.048(2) 0.0005(18) -0.0098(19) -0.024(2)
C1 0.053(3) 0.048(2) 0.040(2) -0.0028(17) -0.0082(18) -0.027(2)
C9 0.054(3) 0.052(2) 0.041(2) -0.0013(18) -0.0056(18) -0.031(2)
O1 0.085(2) 0.0514(18) 0.0591(19) 0.0041(14) -0.0153(15) -0.0396(16)
O2 0.093(2) 0.078(2) 0.0357(16) 0.0088(14) -0.0097(14) -0.0560(18)
C11 0.054(3) 0.049(2) 0.044(2) -0.0026(18) -0.0087(19) -0.023(2)
C10 0.056(3) 0.046(2) 0.032(2) -0.0024(17) -0.0036(18) -0.029(2)
C12 0.061(3) 0.047(2) 0.045(2) -0.0057(18) -0.009(2) -0.027(2)

_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
C8 C7 1.383(4) . ?
C8 C3 1.387(4) . ?
C8 C9 1.468(5) . ?
C4 C5 1.378(4) . ?
C4 C3 1.387(5) . ?
C3 C2 1.468(5) . ?
C7 C6 1.374(5) . ?
C5 C6 1.395(5) . ?
C2 O1 1.211(4) . ?
C2 C1 1.546(5) . ?
C1 C10 1.503(5) . ?
C1 C9 1.521(5) . ?
C9 O2 1.222(4) . ?
C11 C10 1.386(4) . ?
C11 C12 1.391(5) . ?
C10 C12 1.381(5) 2_667 ?
C12 C10 1.381(5) 2_667 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C8 C3 121.4(3) . . ?
C7 C8 C9 128.6(3) . . ?
C3 C8 C9 110.0(3) . . ?
C5 C4 C3 118.4(3) . . ?
C8 C3 C4 120.5(3) . . ?
C8 C3 C2 109.8(3) . . ?
C4 C3 C2 129.7(3) . . ?
C6 C7 C8 117.7(3) . . ?
C4 C5 C6 120.5(4) . . ?
C7 C6 C5 121.5(3) . . ?
O1 C2 C3 126.7(3) . . ?
O1 C2 C1 124.8(3) . . ?
C3 C2 C1 108.5(3) . . ?
C10 C1 C9 117.7(3) . . ?
C10 C1 C2 113.8(3) . . ?
C9 C1 C2 102.2(3) . . ?
O2 C9 C8 125.9(3) . . ?
O2 C9 C1 125.0(3) . . ?
C8 C9 C1 109.1(3) . . ?
C10 C11 C12 120.4(4) . . ?
C12 C10 C11 118.0(3) 2_667 . ?
C12 C10 C1 121.8(3) 2_667 . ?
C11 C10 C1 120.1(4) . . ?
C10 C12 C11 121.6(3) 2_667 . ?

_diffrn_measured_fraction_theta_max 0.876
_diffrn_reflns_theta_full        67.35
_diffrn_measured_fraction_theta_full 0.876
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.056