# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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data_1
_database_code_depnum_ccdc_archive 'CCDC 883582'
#TrackingRef 'compound 1.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C21 H16 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         284.34
_chemical_compound_source        'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P c'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,-y,1/2+z
_cell_length_a                   23.955(4)
_cell_length_b                   7.5099(12)
_cell_length_c                   8.5462(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.195(3)
_cell_angle_gamma                90
_cell_volume                     1531.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.180
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.074
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'SADABS 2009'
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.987
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details           
;
;
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 18.4
# number of measured reflections (redundant set)
_diffrn_reflns_number            11390
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             5662
# number of observed reflections (> n sig(I))
_reflns_number_gt                3580
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details          
;
Refinement on F^2^ for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses 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
observed criterion of F^2^ > 2sigma(F^2^) is used only
for calculating -R-factor-obs 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^)+(0.0168P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
# Permitted for _refine_ls_hydrogen_treatment :
# refall - refined all H parameters
# refxyz - refined H coordinates only
# refU - refined H U only
# noref - no refinement of H parameters
# constr - H parameters constrained
# mixed - some constrained, some independent
# undef - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(17)
# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm = Det. by chiral ref. mol. with known abs.conf
# ad = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn = Det. with reference to synthesis
# unk = Unknown/Arbitrary
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5662
_refine_ls_number_parameters     403
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.17909(10) 0.5976(4) 0.2646(3) 1.000 0.0662(10) . .
C2 C Uani 0.45488(14) 0.2255(5) 0.2797(3) 1.000 0.0471(11) . .
C3 C Uani 0.50558(15) 0.2857(5) 0.2199(4) 1.000 0.0531(14) . .
C6 C Uani 0.35836(14) 0.2824(5) 0.3382(4) 1.000 0.0520(14) . .
C7 C Uani 0.40760(15) 0.3410(5) 0.2729(4) 1.000 0.0482(12) . .
C9 C Uani 0.55321(17) 0.1734(6) 0.2282(4) 1.000 0.0624(17) . .
C15 C Uani 0.45971(16) 0.5683(5) 0.1485(4) 1.000 0.0604(16) . .
C19 C Uani 0.27511(14) 0.5081(5) 0.3326(4) 1.000 0.0550(14) . .
C20 C Uani 0.31179(14) 0.4033(5) 0.3375(4) 1.000 0.0556(14) . .
C21 C Uani 0.40333(18) 0.0020(5) 0.4072(4) 1.000 0.0677(17) . .
C24 C Uani 0.35702(16) 0.1128(5) 0.4039(4) 1.000 0.0639(17) . .
C26 C Uani 0.41233(14) 0.5124(5) 0.2048(4) 1.000 0.0554(14) . .
C27 C Uani 0.45262(16) 0.0544(5) 0.3465(4) 1.000 0.0559(16) . .
C29 C Uani 0.50827(15) 0.4578(5) 0.1535(4) 1.000 0.0538(14) . .
C31 C Uani 0.54867(19) 0.0006(7) 0.2969(5) 1.000 0.0807(19) . .
C34 C Uani 0.23375(14) 0.6576(5) 0.3255(4) 1.000 0.0537(14) . .
C35 C Uani 0.60223(17) 0.2334(7) 0.1694(5) 1.000 0.0812(19) . .
C36 C Uani 0.50155(18) -0.0558(5) 0.3528(4) 1.000 0.0688(17) . .
C37 C Uani 0.55837(17) 0.5122(6) 0.0954(4) 1.000 0.0749(17) . .
C39 C Uani 0.60392(18) 0.3999(8) 0.1025(5) 1.000 0.091(2) . .
C41 C Uani 0.23114(15) 0.7362(4) 0.4879(4) 1.000 0.0681(17) . .
C42 C Uani 0.25079(15) 0.7954(5) 0.2099(4) 1.000 0.0723(17) . .
O2 O Uani 1.12335(10) 0.3904(3) 0.4661(2) 1.000 0.0681(10) . .
C1 C Uani 0.90356(14) 0.2309(4) 0.6573(4) 1.000 0.0479(12) . .
C4 C Uani 0.85998(15) 0.2587(4) 0.7562(4) 1.000 0.0499(12) . .
C5 C Uani 0.87320(16) 0.3083(5) 0.9162(4) 1.000 0.0541(14) . .
C8 C Uani 0.80312(15) 0.2375(4) 0.6966(4) 1.000 0.0530(14) . .
C10 C Uani 0.78969(16) 0.1883(5) 0.5390(5) 1.000 0.0603(16) . .
C11 C Uani 0.95959(14) 0.2582(5) 0.7181(4) 1.000 0.0526(14) . .
C12 C Uani 0.92882(16) 0.3284(5) 0.9718(5) 1.000 0.0641(17) . .
C13 C Uani 0.75970(15) 0.2705(5) 0.7967(5) 1.000 0.0626(16) . .
C14 C Uani 1.00433(15) 0.2454(5) 0.6162(5) 1.000 0.0586(16) . .
C16 C Uani 0.97081(15) 0.3046(5) 0.8753(5) 1.000 0.0662(17) . .
C22 C Uani 0.73363(18) 0.1671(5) 0.4826(5) 1.000 0.0783(17) . .
C23 C Uani 0.77466(18) 0.3205(5) 0.9559(5) 1.000 0.0745(17) . .
C25 C Uani 0.83381(16) 0.1587(5) 0.4416(5) 1.000 0.0659(17) . .
C28 C Uani 1.04112(15) 0.2452(5) 0.5306(4) 1.000 0.0602(16) . .
C30 C Uani 0.88838(16) 0.1804(4) 0.4984(4) 1.000 0.0608(17) . .
C32 C Uani 0.82850(17) 0.3383(5) 1.0122(5) 1.000 0.0700(17) . .
C33 C Uani 1.08565(14) 0.2479(5) 0.4238(4) 1.000 0.0549(14) . .
C38 C Uani 0.69148(19) 0.1980(6) 0.5793(7) 1.000 0.094(2) . .
C40 C Uani 1.06208(15) 0.2828(5) 0.2566(4) 1.000 0.0710(17) . .
C43 C Uani 0.70387(17) 0.2489(6) 0.7323(7) 1.000 0.090(2) . .
C44 C Uani 1.11725(16) 0.0721(5) 0.4339(5) 1.000 0.0841(17) . .
H1 H Uiso 0.16590 0.53360 0.32960 1.000 0.0990 calc R
H15 H Uiso 0.46100 0.68160 0.10520 1.000 0.0730 calc R
H21 H Uiso 0.40140 -0.11080 0.45120 1.000 0.0810 calc R
H24 H Uiso 0.32470 0.07370 0.44610 1.000 0.0770 calc R
H26 H Uiso 0.38150 0.58820 0.19920 1.000 0.0670 calc R
H31 H Uiso 0.57960 -0.07470 0.30270 1.000 0.0970 calc R
H35 H Uiso 0.63380 0.16100 0.17530 1.000 0.0970 calc R
H36 H Uiso 0.50050 -0.16890 0.39680 1.000 0.0830 calc R
H37 H Uiso 0.56090 0.62500 0.05170 1.000 0.0900 calc R
H39 H Uiso 0.63660 0.43730 0.06130 1.000 0.1090 calc R
H41A H Uiso 0.20610 0.83630 0.48190 1.000 0.1020 calc R
H41B H Uiso 0.26790 0.77420 0.52840 1.000 0.1020 calc R
H41C H Uiso 0.21770 0.64770 0.55640 1.000 0.1020 calc R
H42A H Uiso 0.25010 0.74300 0.10730 1.000 0.1080 calc R
H42B H Uiso 0.28800 0.83690 0.24210 1.000 0.1080 calc R
H42C H Uiso 0.22510 0.89370 0.20700 1.000 0.1080 calc R
H2 H Uiso 1.13580 0.37940 0.55820 1.000 0.1020 calc R
H12 H Uiso 0.93790 0.35860 1.07660 1.000 0.0770 calc R
H16 H Uiso 1.00780 0.31980 0.91600 1.000 0.0790 calc R
H22 H Uiso 0.72450 0.13180 0.37910 1.000 0.0940 calc R
H23 H Uiso 0.74660 0.34130 1.02200 1.000 0.0890 calc R
H25 H Uiso 0.82530 0.12410 0.33770 1.000 0.0790 calc R
H30 H Uiso 0.91640 0.16180 0.43180 1.000 0.0730 calc R
H32 H Uiso 0.83690 0.37110 1.11670 1.000 0.0840 calc R
H38 H Uiso 0.65420 0.18410 0.54010 1.000 0.1130 calc R
H40A H Uiso 1.04270 0.39490 0.25140 1.000 0.1060 calc R
H40B H Uiso 1.03640 0.18940 0.22260 1.000 0.1060 calc R
H40C H Uiso 1.09210 0.28640 0.18950 1.000 0.1060 calc R
H43 H Uiso 0.67480 0.26960 0.79510 1.000 0.1080 calc R
H44A H Uiso 1.14710 0.07610 0.36630 1.000 0.1260 calc R
H44B H Uiso 1.09210 -0.02310 0.40140 1.000 0.1260 calc R
H44C H Uiso 1.13250 0.05220 0.54020 1.000 0.1260 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 0.0425(14) 0.101(2) 0.0533(15) 0.0154(14) -0.0059(12) -0.0106(14)
C2 0.055(2) 0.053(2) 0.0315(19) -0.0012(17) -0.0059(17) 0.009(2)
C3 0.048(2) 0.065(3) 0.045(2) -0.0108(19) -0.0033(18) 0.008(2)
C6 0.048(2) 0.059(3) 0.048(2) -0.0086(19) -0.0015(18) -0.002(2)
C7 0.054(2) 0.049(2) 0.040(2) 0.0009(17) -0.0052(17) 0.0049(19)
C9 0.058(3) 0.070(3) 0.057(3) -0.011(2) -0.006(2) 0.007(2)
C15 0.070(3) 0.056(3) 0.054(2) 0.007(2) -0.001(2) -0.001(2)
C19 0.042(2) 0.073(3) 0.050(2) -0.0072(19) 0.0041(17) -0.001(2)
C20 0.042(2) 0.070(3) 0.055(2) -0.009(2) 0.0052(19) -0.001(2)
C21 0.091(3) 0.051(3) 0.060(3) 0.001(2) 0.001(2) -0.002(3)
C24 0.065(3) 0.064(3) 0.063(3) -0.002(2) 0.007(2) -0.008(2)
C26 0.052(2) 0.060(3) 0.053(2) 0.0046(19) -0.0011(19) 0.009(2)
C27 0.064(3) 0.057(3) 0.046(2) -0.004(2) 0.001(2) 0.008(2)
C29 0.052(2) 0.064(3) 0.045(2) -0.002(2) 0.0015(18) -0.002(2)
C31 0.076(3) 0.092(4) 0.071(3) -0.013(3) -0.010(2) 0.033(3)
C34 0.042(2) 0.073(3) 0.045(2) 0.0027(19) -0.0016(16) 0.001(2)
C35 0.057(3) 0.107(4) 0.078(3) -0.021(3) -0.003(2) 0.014(3)
C36 0.090(3) 0.059(3) 0.055(3) -0.003(2) -0.007(2) 0.025(3)
C37 0.068(3) 0.082(3) 0.075(3) -0.002(3) 0.008(3) -0.010(3)
C39 0.065(3) 0.123(5) 0.087(4) -0.024(3) 0.011(3) -0.004(3)
C41 0.072(3) 0.075(3) 0.057(3) -0.004(2) 0.005(2) 0.015(2)
C42 0.066(3) 0.085(3) 0.066(3) 0.014(2) 0.006(2) -0.011(2)
O2 0.0606(16) 0.0967(19) 0.0460(15) 0.0052(15) -0.0001(13) -0.0229(16)
C1 0.051(2) 0.039(2) 0.054(2) -0.0021(17) 0.0066(19) 0.0012(18)
C4 0.054(2) 0.039(2) 0.056(2) 0.0007(18) 0.0012(19) -0.0005(17)
C5 0.054(2) 0.048(2) 0.062(3) 0.0044(19) 0.014(2) -0.002(2)
C8 0.049(2) 0.039(2) 0.070(3) 0.0020(19) 0.000(2) -0.0022(17)
C10 0.045(2) 0.055(3) 0.079(3) -0.007(2) -0.005(2) -0.001(2)
C11 0.041(2) 0.057(3) 0.060(2) 0.004(2) 0.0054(19) 0.0015(19)
C12 0.059(3) 0.074(3) 0.059(3) 0.000(2) 0.003(2) -0.013(2)
C13 0.043(2) 0.054(3) 0.092(3) 0.001(2) 0.013(2) -0.003(2)
C14 0.042(2) 0.064(3) 0.068(3) -0.004(2) -0.004(2) 0.006(2)
C16 0.049(3) 0.077(3) 0.071(3) 0.004(2) -0.004(2) -0.009(2)
C22 0.067(3) 0.075(3) 0.089(3) -0.010(3) -0.015(3) -0.001(3)
C23 0.076(3) 0.074(3) 0.077(3) -0.002(3) 0.027(3) 0.000(3)
C25 0.064(3) 0.061(3) 0.070(3) -0.011(2) -0.009(2) 0.000(2)
C28 0.041(2) 0.070(3) 0.069(3) -0.003(2) 0.002(2) 0.001(2)
C30 0.064(3) 0.060(3) 0.059(3) -0.008(2) 0.009(2) 0.001(2)
C32 0.074(3) 0.070(3) 0.067(3) -0.004(2) 0.012(3) -0.002(3)
C33 0.040(2) 0.068(3) 0.056(2) 0.002(2) -0.0002(18) 0.005(2)
C38 0.057(3) 0.098(4) 0.125(4) -0.007(3) -0.010(3) -0.001(3)
C40 0.066(3) 0.083(3) 0.061(3) 0.000(2) -0.011(2) 0.000(2)
C43 0.053(3) 0.084(4) 0.135(5) 0.008(3) 0.017(3) 0.004(3)
C44 0.079(3) 0.091(3) 0.083(3) 0.008(3) 0.011(2) 0.025(3)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C34 1.437(4) . . yes
O1 H1 0.8200 . . no
O2 C33 1.426(4) . . yes
O2 H2 0.8200 . . no
C2 C7 1.424(5) . . no
C2 C27 1.409(5) . . no
C2 C3 1.433(5) . . no
C3 C9 1.415(6) . . no
C3 C29 1.415(5) . . no
C6 C20 1.438(5) . . no
C6 C24 1.394(5) . . no
C6 C7 1.420(5) . . no
C7 C26 1.421(5) . . no
C9 C31 1.433(7) . . no
C9 C35 1.393(6) . . no
C15 C29 1.426(5) . . no
C15 C26 1.340(5) . . no
C19 C20 1.178(5) . . no
C19 C34 1.495(5) . . no
C21 C24 1.385(6) . . no
C21 C27 1.389(6) . . no
C27 C36 1.432(6) . . no
C29 C37 1.401(5) . . no
C31 C36 1.334(6) . . no
C34 C42 1.512(5) . . no
C34 C41 1.515(5) . . no
C35 C39 1.377(8) . . no
C37 C39 1.376(7) . . no
C15 H15 0.9300 . . no
C21 H21 0.9300 . . no
C24 H24 0.9300 . . no
C26 H26 0.9300 . . no
C31 H31 0.9300 . . no
C35 H35 0.9300 . . no
C36 H36 0.9300 . . no
C37 H37 0.9300 . . no
C39 H39 0.9300 . . no
C41 H41B 0.9600 . . no
C41 H41C 0.9600 . . no
C41 H41A 0.9600 . . no
C42 H42B 0.9600 . . no
C42 H42C 0.9600 . . no
C42 H42A 0.9600 . . no
C1 C4 1.417(5) . . no
C1 C11 1.410(5) . . no
C1 C30 1.425(5) . . no
C4 C8 1.419(5) . . no
C4 C5 1.425(5) . . no
C5 C12 1.382(5) . . no
C5 C32 1.425(6) . . no
C8 C10 1.406(5) . . no
C8 C13 1.427(5) . . no
C10 C25 1.421(6) . . no
C10 C22 1.394(6) . . no
C11 C16 1.390(5) . . no
C11 C14 1.444(5) . . no
C12 C16 1.369(6) . . no
C13 C43 1.409(6) . . no
C13 C23 1.426(6) . . no
C14 C28 1.195(5) . . no
C22 C38 1.381(7) . . no
C23 C32 1.342(6) . . no
C25 C30 1.362(5) . . no
C28 C33 1.466(5) . . no
C33 C44 1.520(5) . . no
C33 C40 1.511(5) . . no
C38 C43 1.369(8) . . no
C12 H12 0.9300 . . no
C16 H16 0.9300 . . no
C22 H22 0.9300 . . no
C23 H23 0.9300 . . no
C25 H25 0.9300 . . no
C30 H30 0.9300 . . no
C32 H32 0.9300 . . no
C38 H38 0.9300 . . no
C40 H40A 0.9600 . . no
C40 H40B 0.9600 . . no
C40 H40C 0.9600 . . no
C43 H43 0.9300 . . no
C44 H44A 0.9600 . . no
C44 H44B 0.9600 . . no
C44 H44C 0.9600 . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C34 O1 H1 109.00 . . . no
C33 O2 H2 110.00 . . . no
C3 C2 C27 119.8(3) . . . no
C7 C2 C27 120.8(3) . . . no
C3 C2 C7 119.4(3) . . . no
C9 C3 C29 119.9(3) . . . no
C2 C3 C9 120.0(3) . . . no
C2 C3 C29 120.1(3) . . . no
C20 C6 C24 122.2(3) . . . no
C7 C6 C24 119.5(3) . . . no
C7 C6 C20 118.3(3) . . . no
C6 C7 C26 122.8(3) . . . no
C2 C7 C26 118.4(3) . . . no
C2 C7 C6 118.8(3) . . . no
C3 C9 C31 118.0(4) . . . no
C31 C9 C35 122.6(4) . . . no
C3 C9 C35 119.4(4) . . . no
C26 C15 C29 121.5(3) . . . no
C20 C19 C34 173.2(4) . . . no
C6 C20 C19 176.7(4) . . . no
C24 C21 C27 121.9(3) . . . no
C6 C24 C21 120.6(3) . . . no
C7 C26 C15 122.2(3) . . . no
C2 C27 C21 118.4(3) . . . no
C21 C27 C36 122.9(3) . . . no
C2 C27 C36 118.8(3) . . . no
C3 C29 C37 118.7(3) . . . no
C3 C29 C15 118.5(3) . . . no
C15 C29 C37 122.8(4) . . . no
C9 C31 C36 122.2(4) . . . no
O1 C34 C42 105.6(3) . . . yes
O1 C34 C19 111.0(3) . . . yes
C19 C34 C42 108.9(3) . . . no
C41 C34 C42 111.6(3) . . . no
O1 C34 C41 110.0(3) . . . yes
C19 C34 C41 109.7(3) . . . no
C9 C35 C39 120.1(4) . . . no
C27 C36 C31 121.3(4) . . . no
C29 C37 C39 120.5(4) . . . no
C35 C39 C37 121.5(4) . . . no
C26 C15 H15 119.00 . . . no
C29 C15 H15 119.00 . . . no
C27 C21 H21 119.00 . . . no
C24 C21 H21 119.00 . . . no
C6 C24 H24 120.00 . . . no
C21 C24 H24 120.00 . . . no
C15 C26 H26 119.00 . . . no
C7 C26 H26 119.00 . . . no
C36 C31 H31 119.00 . . . no
C9 C31 H31 119.00 . . . no
C9 C35 H35 120.00 . . . no
C39 C35 H35 120.00 . . . no
C31 C36 H36 119.00 . . . no
C27 C36 H36 119.00 . . . no
C29 C37 H37 120.00 . . . no
C39 C37 H37 120.00 . . . no
C37 C39 H39 119.00 . . . no
C35 C39 H39 119.00 . . . no
C34 C41 H41A 109.00 . . . no
C34 C41 H41C 109.00 . . . no
H41A C41 H41B 110.00 . . . no
C34 C41 H41B 109.00 . . . no
H41B C41 H41C 109.00 . . . no
H41A C41 H41C 109.00 . . . no
C34 C42 H42B 109.00 . . . no
C34 C42 H42C 109.00 . . . no
C34 C42 H42A 109.00 . . . no
H42A C42 H42C 109.00 . . . no
H42B C42 H42C 110.00 . . . no
H42A C42 H42B 109.00 . . . no
C4 C1 C30 118.0(3) . . . no
C11 C1 C30 122.8(3) . . . no
C4 C1 C11 119.2(3) . . . no
C1 C4 C5 120.0(3) . . . no
C5 C4 C8 119.8(3) . . . no
C1 C4 C8 120.3(3) . . . no
C4 C5 C12 118.8(3) . . . no
C12 C5 C32 122.4(3) . . . no
C4 C5 C32 118.7(3) . . . no
C4 C8 C13 119.6(3) . . . no
C10 C8 C13 120.3(3) . . . no
C4 C8 C10 120.2(3) . . . no
C8 C10 C22 119.4(4) . . . no
C22 C10 C25 121.6(4) . . . no
C8 C10 C25 119.0(4) . . . no
C1 C11 C14 120.1(3) . . . no
C14 C11 C16 120.7(3) . . . no
C1 C11 C16 119.1(3) . . . no
C5 C12 C16 121.1(4) . . . no
C8 C13 C23 119.0(3) . . . no
C23 C13 C43 123.4(4) . . . no
C8 C13 C43 117.6(4) . . . no
C11 C14 C28 176.2(4) . . . no
C11 C16 C12 121.8(3) . . . no
C10 C22 C38 120.5(4) . . . no
C13 C23 C32 121.3(4) . . . no
C10 C25 C30 120.9(4) . . . no
C14 C28 C33 178.8(4) . . . no
C1 C30 C25 121.7(3) . . . no
C5 C32 C23 121.7(4) . . . no
O2 C33 C28 109.4(3) . . . yes
O2 C33 C44 109.7(3) . . . yes
C28 C33 C40 111.1(3) . . . no
C28 C33 C44 109.8(3) . . . no
C40 C33 C44 110.2(3) . . . no
O2 C33 C40 106.5(3) . . . yes
C22 C38 C43 120.8(4) . . . no
C13 C43 C38 121.4(4) . . . no
C5 C12 H12 119.00 . . . no
C16 C12 H12 119.00 . . . no
C11 C16 H16 119.00 . . . no
C12 C16 H16 119.00 . . . no
C10 C22 H22 120.00 . . . no
C38 C22 H22 120.00 . . . no
C13 C23 H23 119.00 . . . no
C32 C23 H23 119.00 . . . no
C10 C25 H25 120.00 . . . no
C30 C25 H25 120.00 . . . no
C1 C30 H30 119.00 . . . no
C25 C30 H30 119.00 . . . no
C5 C32 H32 119.00 . . . no
C23 C32 H32 119.00 . . . no
C22 C38 H38 120.00 . . . no
C43 C38 H38 120.00 . . . no
C33 C40 H40A 109.00 . . . no
C33 C40 H40B 109.00 . . . no
C33 C40 H40C 110.00 . . . no
H40A C40 H40B 109.00 . . . no
H40A C40 H40C 109.00 . . . no
H40B C40 H40C 109.00 . . . no
C13 C43 H43 119.00 . . . no
C38 C43 H43 119.00 . . . no
C33 C44 H44A 109.00 . . . no
C33 C44 H44B 110.00 . . . no
C33 C44 H44C 110.00 . . . no
H44A C44 H44B 109.00 . . . no
H44A C44 H44C 110.00 . . . no
H44B C44 H44C 109.00 . . . no
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 C2 C3 C9 179.0(3) . . . . no
C7 C2 C3 C29 -0.6(5) . . . . no
C27 C2 C3 C9 -0.1(5) . . . . no
C27 C2 C3 C29 -179.6(3) . . . . no
C3 C2 C7 C6 -177.5(3) . . . . no
C3 C2 C7 C26 0.7(5) . . . . no
C27 C2 C7 C6 1.5(5) . . . . no
C27 C2 C7 C26 179.7(3) . . . . no
C3 C2 C27 C21 178.3(3) . . . . no
C3 C2 C27 C36 0.0(5) . . . . no
C7 C2 C27 C21 -0.7(5) . . . . no
C7 C2 C27 C36 -179.1(3) . . . . no
C2 C3 C9 C31 0.2(5) . . . . no
C2 C3 C9 C35 179.9(3) . . . . no
C29 C3 C9 C31 179.8(3) . . . . no
C29 C3 C9 C35 -0.6(5) . . . . no
C2 C3 C29 C15 0.2(5) . . . . no
C2 C3 C29 C37 -179.7(3) . . . . no
C9 C3 C29 C15 -179.3(3) . . . . no
C9 C3 C29 C37 0.8(5) . . . . no
C20 C6 C7 C2 177.1(3) . . . . no
C20 C6 C7 C26 -1.1(5) . . . . no
C24 C6 C7 C2 -1.4(5) . . . . no
C24 C6 C7 C26 -179.6(3) . . . . no
C7 C6 C24 C21 0.6(5) . . . . no
C20 C6 C24 C21 -177.8(3) . . . . no
C2 C7 C26 C15 -0.5(5) . . . . no
C6 C7 C26 C15 177.6(3) . . . . no
C3 C9 C31 C36 -0.3(6) . . . . no
C35 C9 C31 C36 -180.0(4) . . . . no
C3 C9 C35 C39 -0.7(6) . . . . no
C31 C9 C35 C39 179.0(4) . . . . no
C29 C15 C26 C7 0.2(5) . . . . no
C26 C15 C29 C3 0.0(5) . . . . no
C26 C15 C29 C37 179.9(3) . . . . no
C27 C21 C24 C6 0.2(5) . . . . no
C24 C21 C27 C2 -0.1(5) . . . . no
C24 C21 C27 C36 178.1(3) . . . . no
C2 C27 C36 C31 0.0(5) . . . . no
C21 C27 C36 C31 -178.3(4) . . . . no
C3 C29 C37 C39 0.2(6) . . . . no
C15 C29 C37 C39 -179.7(4) . . . . no
C9 C31 C36 C27 0.2(6) . . . . no
C9 C35 C39 C37 1.7(7) . . . . no
C29 C37 C39 C35 -1.4(6) . . . . no
C11 C1 C4 C5 -1.9(5) . . . . no
C11 C1 C4 C8 178.1(3) . . . . no
C30 C1 C4 C5 179.6(3) . . . . no
C30 C1 C4 C8 -0.4(4) . . . . no
C4 C1 C11 C14 -174.8(3) . . . . no
C4 C1 C11 C16 2.6(5) . . . . no
C30 C1 C11 C14 3.6(5) . . . . no
C30 C1 C11 C16 -179.0(3) . . . . no
C4 C1 C30 C25 -0.1(5) . . . . no
C11 C1 C30 C25 -178.5(3) . . . . no
C1 C4 C5 C12 0.0(5) . . . . no
C1 C4 C5 C32 179.0(3) . . . . no
C8 C4 C5 C12 -179.9(3) . . . . no
C8 C4 C5 C32 -1.0(5) . . . . no
C1 C4 C8 C10 0.2(5) . . . . no
C1 C4 C8 C13 -178.4(3) . . . . no
C5 C4 C8 C10 -179.9(3) . . . . no
C5 C4 C8 C13 1.6(5) . . . . no
C4 C5 C12 C16 1.2(6) . . . . no
C32 C5 C12 C16 -177.7(4) . . . . no
C4 C5 C32 C23 0.2(6) . . . . no
C12 C5 C32 C23 179.1(4) . . . . no
C4 C8 C10 C22 179.7(3) . . . . no
C4 C8 C10 C25 0.6(5) . . . . no
C13 C8 C10 C22 -1.8(5) . . . . no
C13 C8 C10 C25 179.1(3) . . . . no
C4 C8 C13 C23 -1.3(5) . . . . no
C4 C8 C13 C43 179.6(3) . . . . no
C10 C8 C13 C23 -179.9(3) . . . . no
C10 C8 C13 C43 1.1(5) . . . . no
C8 C10 C22 C38 1.5(6) . . . . no
C25 C10 C22 C38 -179.5(4) . . . . no
C8 C10 C25 C30 -1.1(5) . . . . no
C22 C10 C25 C30 179.8(3) . . . . no
C1 C11 C16 C12 -1.5(6) . . . . no
C14 C11 C16 C12 175.9(4) . . . . no
C5 C12 C16 C11 -0.4(6) . . . . no
C8 C13 C23 C32 0.6(6) . . . . no
C43 C13 C23 C32 179.6(4) . . . . no
C8 C13 C43 C38 0.0(6) . . . . no
C23 C13 C43 C38 -179.0(4) . . . . no
C10 C22 C38 C43 -0.4(7) . . . . no
C13 C23 C32 C5 0.0(6) . . . . no
C10 C25 C30 C1 0.9(5) . . . . no
C22 C38 C43 C13 -0.4(7) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O2 2.754(3) . 1_455 no
O1 O2 2.772(3) . 2_464 no
O2 O1 2.772(3) . 2_665 no
O2 O1 2.754(3) . 1_655 no
O1 H2 1.9700 . 2_464 no
O1 H41C 2.7800 . 2_564 no
O2 H1 1.9400 . 1_655 no
C2 C15 3.504(5) . 2_565 no
C3 C36 3.575(5) . 2_554 no
C4 C25 3.593(5) . 2_555 no
C7 C15 3.406(5) . 2_565 no
C9 C36 3.448(5) . 2_554 no
C15 C7 3.406(5) . 2_564 no
C15 C2 3.504(5) . 2_564 no
C15 C36 3.421(5) . 1_565 no
C19 C41 3.549(5) . 2_564 no
C19 C26 3.557(5) . . no
C20 C41 3.565(5) . 2_564 no
C25 C4 3.593(5) . 2_554 no
C26 C19 3.557(5) . . no
C36 C15 3.421(5) . 1_545 no
C36 C3 3.575(5) . 2_555 no
C36 C9 3.448(5) . 2_555 no
C41 C20 3.565(5) . 2_565 no
C41 C19 3.549(5) . 2_565 no
C2 H15 2.8600 . 2_565 no
C3 H37 3.0900 . 2_565 no
C3 H36 2.8900 . 2_554 no
C4 H32 3.0600 . 2_564 no
C4 H25 3.0900 . 2_555 no
C7 H15 3.0100 . 2_565 no
C8 H25 3.0000 . 2_555 no
C9 H36 2.9900 . 2_554 no
C14 H30 2.5900 . . no
C14 H40A 3.0500 . 2_565 no
C15 H36 3.0000 . 1_565 no
C16 H40A 3.0800 . 2_565 no
C19 H41C 2.8700 . 2_564 no
C19 H26 2.9500 . . no
C20 H26 2.5400 . . no
C20 H42A 3.0500 . 2_565 no
C20 H41B 3.0600 . 2_564 no
C24 H42B 2.9200 . 1_545 no
C27 H15 2.9600 . 2_565 no
C28 H30 3.0900 . . no
C29 H36 3.0800 . 2_554 no
C33 H1 3.0400 . 1_655 no
C36 H15 2.9900 . 1_545 no
C38 H39 3.0400 . 2_565 no
C40 H16 3.0900 . 1_554 no
C44 H41A 2.7700 . 1_645 no
H1 O2 1.9400 . 1_455 no
H1 H2 2.4400 . 1_455 no
H1 H41C 2.3700 . . no
H1 H2 2.4500 . 2_464 no
H1 C33 3.0400 . 1_455 no
H2 H1 2.4400 . 1_655 no
H2 H44C 2.4600 . . no
H2 H1 2.4500 . 2_665 no
H2 O1 1.9700 . 2_665 no
H12 H32 2.4800 . . no
H15 C2 2.8600 . 2_564 no
H15 C36 2.9900 . 1_565 no
H15 H37 2.5100 . . no
H15 C7 3.0100 . 2_564 no
H15 C27 2.9600 . 2_564 no
H16 C40 3.0900 . 1_556 no
H21 H36 2.5000 . . no
H22 H25 2.4700 . . no
H23 H43 2.5300 . . no
H24 H42B 2.5900 . 1_545 no
H25 H22 2.4700 . . no
H25 C4 3.0900 . 2_554 no
H25 C8 3.0000 . 2_554 no
H26 C19 2.9500 . . no
H26 C20 2.5400 . . no
H30 C14 2.5900 . . no
H30 C28 3.0900 . . no
H31 H35 2.5000 . . no
H32 H12 2.4800 . . no
H32 C4 3.0600 . 2_565 no
H35 H31 2.5000 . . no
H36 C15 3.0000 . 1_545 no
H36 H21 2.5000 . . no
H36 C3 2.8900 . 2_555 no
H36 C9 2.9900 . 2_555 no
H36 C29 3.0800 . 2_555 no
H37 H15 2.5100 . . no
H37 C3 3.0900 . 2_564 no
H39 C38 3.0400 . 2_564 no
H40A C14 3.0500 . 2_564 no
H40A C16 3.0800 . 2_564 no
H40B H44B 2.5100 . . no
H40C H44A 2.4800 . . no
H41A H44C 2.4800 . 1_465 no
H41A C44 2.7700 . 1_465 no
H41A H42C 2.4700 . . no
H41A H44A 2.4400 . 1_465 no
H41B C20 3.0600 . 2_565 no
H41B H42B 2.5800 . . no
H41C H1 2.3700 . . no
H41C O1 2.7800 . 2_565 no
H41C C19 2.8700 . 2_565 no
H42A C20 3.0500 . 2_564 no
H42B C24 2.9200 . 1_565 no
H42B H41B 2.5800 . . no
H42B H24 2.5900 . 1_565 no
H42C H41A 2.4700 . . no
H42C H44C 2.5600 . 2_464 no
H43 H23 2.5300 . . no
H44A H40C 2.4800 . . no
H44A H41A 2.4400 . 1_645 no
H44B H40B 2.5100 . . no
H44C H2 2.4600 . . no
H44C H41A 2.4800 . 1_645 no
H44C H42C 2.5600 . 2_665 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O1 H1 O2 0.8200 1.9400 2.754(3) 171.00 1_455 yes
O2 H2 O1 0.8200 1.9700 2.772(3) 165.00 2_665 yes


data_3_b
_database_code_depnum_ccdc_archive 'CCDC 883583'
#TrackingRef 'compound 3.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 O4'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C36 H34 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         530.63
_chemical_compound_source        'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z
_cell_length_a                   16.8215(8)
_cell_length_b                   24.9185(14)
_cell_length_c                   7.4008(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3102.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    1218
_cell_measurement_theta_min      2.4195
_cell_measurement_theta_max      32.6647
_cell_special_details            
;
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.073
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.994
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details           
;
;
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measurement_method       '\w scans'
# number of measured reflections (redundant set)
_diffrn_reflns_number            18311
_diffrn_reflns_av_R_equivalents  0.1727
_diffrn_reflns_av_sigmaI/netI    0.0963
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2734
# number of observed reflections (> n sig(I))
_reflns_number_gt                1156
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details          
;
Refinement on F^2^ for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses 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
observed criterion of F^2^ > 2sigma(F^2^) is used only
for calculating -R-factor-obs 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^)+(0.1330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
# Permitted for _refine_ls_hydrogen_treatment :
# refall - refined all H parameters
# refxyz - refined H coordinates only
# refU - refined H U only
# noref - no refinement of H parameters
# constr - H parameters constrained
# mixed - some constrained, some independent
# undef - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2734
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.2771
_refine_ls_wR_factor_gt          0.2172
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O31 O Uani 0.4462(3) 0.19685(16) 0.6149(6) 1.000 0.132(2) . .
O50 O Uani 0.92308(16) 0.40935(11) 0.3100(4) 1.000 0.0686(11) . .
C1 C Uani 0.5987(2) 0.37776(16) 0.4246(5) 1.000 0.0510(14) . .
C2 C Uani 0.6393(2) 0.42565(14) 0.3949(5) 1.000 0.0440(12) . .
C3 C Uani 0.5999(2) 0.47538(14) 0.4236(4) 1.000 0.0402(11) . .
C4 C Uani 0.5199(2) 0.47550(13) 0.4840(4) 1.000 0.0390(12) . .
C5 C Uani 0.6391(2) 0.52564(15) 0.3944(5) 1.000 0.0480(14) . .
C6 C Uani 0.3993(2) 0.42751(15) 0.5762(5) 1.000 0.0483(12) . .
C7 C Uani 0.8643(2) 0.42658(15) 0.1815(6) 1.000 0.0537(16) . .
C8 C Uani 0.8843(3) 0.48434(17) 0.1334(6) 1.000 0.0740(17) . .
C10 C Uani 0.7846(2) 0.42457(15) 0.2691(5) 1.000 0.0543(16) . .
C11 C Uani 0.7210(2) 0.42401(15) 0.3291(5) 1.000 0.0480(14) . .
C20 C Uani 0.4792(2) 0.32637(17) 0.5024(5) 1.000 0.0503(17) . .
C21 C Uani 0.4438(3) 0.28575(18) 0.5164(6) 1.000 0.0623(17) . .
C22 C Uani 0.5201(2) 0.37699(15) 0.4816(5) 1.000 0.0473(14) . .
C23 C Uani 0.4793(2) 0.42570(15) 0.5147(5) 1.000 0.0420(12) . .
C25 C Uani 0.3971(3) 0.23578(18) 0.5331(7) 1.000 0.0757(19) . .
C51 C Uani 0.8655(3) 0.3911(2) 0.0138(6) 1.000 0.083(2) . .
C103 C Uani 0.3255(4) 0.2454(3) 0.6417(13) 1.000 0.203(6) . .
C105 C Uani 0.3757(4) 0.2137(3) 0.3501(9) 1.000 0.162(4) . .
H1 H Uiso 0.62500 0.34540 0.40570 1.000 0.0610 calc R
H5 H Uiso 0.69160 0.52610 0.35480 1.000 0.0570 calc R
H6 H Uiso 0.37250 0.39540 0.59690 1.000 0.0580 calc R
H8A H Uiso 0.88710 0.50540 0.24170 1.000 0.1110 calc R
H8B H Uiso 0.84370 0.49860 0.05560 1.000 0.1110 calc R
H8C H Uiso 0.93460 0.48550 0.07230 1.000 0.1110 calc R
H10A H Uiso 0.29450 0.21310 0.64730 1.000 0.3050 calc R
H10B H Uiso 0.29460 0.27350 0.58720 1.000 0.3050 calc R
H10C H Uiso 0.34070 0.25590 0.76170 1.000 0.3050 calc R
H10D H Uiso 0.42330 0.20360 0.28710 1.000 0.2430 calc R
H10E H Uiso 0.34790 0.24050 0.28200 1.000 0.2430 calc R
H10F H Uiso 0.34230 0.18270 0.36450 1.000 0.2430 calc R
H31 H Uiso 0.43910 0.19710 0.72450 1.000 0.1980 calc R
H50 H Uiso 0.91800 0.37710 0.32880 1.000 0.1030 calc R
H51A H Uiso 0.91700 0.39290 -0.04160 1.000 0.1240 calc R
H51B H Uiso 0.82600 0.40350 -0.07020 1.000 0.1240 calc R
H51C H Uiso 0.85410 0.35470 0.04760 1.000 0.1240 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
O31 0.132(4) 0.077(2) 0.186(4) 0.043(3) -0.065(3) -0.025(2)
O50 0.0495(17) 0.0664(19) 0.090(2) 0.0135(16) -0.0014(16) 0.0127(15)
C1 0.043(2) 0.056(2) 0.054(3) -0.0010(19) 0.002(2) 0.011(2)
C2 0.036(2) 0.054(2) 0.042(2) -0.0024(18) 0.0010(17) 0.0016(19)
C3 0.0276(19) 0.053(2) 0.040(2) 0.0016(17) -0.0045(17) -0.0040(17)
C4 0.032(2) 0.048(2) 0.037(2) 0.0009(17) -0.0023(16) -0.0021(16)
C5 0.030(2) 0.063(3) 0.051(2) -0.0007(19) 0.0008(18) -0.004(2)
C6 0.041(2) 0.053(2) 0.051(2) 0.0004(18) 0.0047(19) -0.005(2)
C7 0.039(2) 0.055(3) 0.067(3) 0.005(2) 0.005(2) 0.006(2)
C8 0.074(3) 0.072(3) 0.076(3) 0.012(2) 0.008(3) -0.008(3)
C10 0.047(3) 0.052(2) 0.064(3) 0.0025(19) -0.002(2) 0.009(2)
C11 0.030(2) 0.060(3) 0.054(2) -0.0038(19) 0.0035(19) 0.0001(19)
C20 0.044(3) 0.051(3) 0.056(3) -0.002(2) 0.001(2) 0.004(2)
C21 0.054(3) 0.057(3) 0.076(3) 0.005(2) -0.003(2) 0.004(2)
C22 0.046(3) 0.050(2) 0.046(2) -0.0009(18) -0.0004(19) 0.0009(19)
C23 0.034(2) 0.056(2) 0.036(2) -0.0020(18) 0.0000(16) -0.0007(18)
C25 0.054(3) 0.056(3) 0.117(4) 0.018(3) -0.014(3) -0.003(2)
C51 0.079(4) 0.084(3) 0.085(4) -0.024(3) 0.019(3) 0.008(3)
C103 0.136(7) 0.116(6) 0.358(14) 0.007(7) 0.141(8) -0.025(5)
C105 0.196(8) 0.128(6) 0.163(7) -0.007(5) -0.086(6) -0.069(5)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O31 C25 1.411(7) . . yes
O50 C7 1.438(5) . . yes
O31 H31 0.8200 . . no
O50 H50 0.8200 . . no
C1 C22 1.388(5) . . no
C1 C2 1.392(5) . . no
C2 C3 1.421(5) . . no
C2 C11 1.459(5) . . no
C3 C4 1.418(5) . . no
C3 C5 1.432(5) . . no
C4 C23 1.435(5) . . no
C4 C4 1.413(5) . 5_666 no
C5 C6 1.352(5) . 5_666 no
C6 C23 1.421(5) . . no
C7 C51 1.524(6) . . no
C7 C8 1.520(6) . . no
C7 C10 1.490(5) . . no
C10 C11 1.158(5) . . no
C20 C22 1.445(5) . . no
C20 C21 1.179(6) . . no
C21 C25 1.477(7) . . no
C22 C23 1.416(5) . . no
C25 C105 1.506(8) . . no
C25 C103 1.468(9) . . no
C1 H1 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C8 H8A 0.9600 . . no
C8 H8B 0.9600 . . no
C8 H8C 0.9600 . . no
C51 H51A 0.9600 . . no
C51 H51B 0.9600 . . no
C51 H51C 0.9600 . . no
C103 H10A 0.9600 . . no
C103 H10B 0.9600 . . no
C103 H10C 0.9600 . . no
C105 H10D 0.9600 . . no
C105 H10E 0.9600 . . no
C105 H10F 0.9600 . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O31 H31 110.00 . . . no
C7 O50 H50 109.00 . . . no
C2 C1 C22 121.8(3) . . . no
C1 C2 C11 119.4(3) . . . no
C1 C2 C3 119.7(3) . . . no
C3 C2 C11 120.9(3) . . . no
C4 C3 C5 118.9(3) . . . no
C2 C3 C4 119.4(3) . . . no
C2 C3 C5 121.7(3) . . . no
C3 C4 C4 120.3(3) . . 5_666 no
C3 C4 C23 120.0(3) . . . no
C4 C4 C23 119.7(3) 5_666 . . no
C3 C5 C6 120.7(3) . . 5_666 no
C5 C6 C23 122.1(3) 5_666 . . no
O50 C7 C51 110.9(3) . . . yes
C8 C7 C10 109.4(3) . . . no
C8 C7 C51 110.8(4) . . . no
C10 C7 C51 110.3(3) . . . no
O50 C7 C8 106.6(3) . . . yes
O50 C7 C10 108.7(3) . . . yes
C7 C10 C11 176.5(4) . . . no
C2 C11 C10 176.2(4) . . . no
C21 C20 C22 177.9(4) . . . no
C20 C21 C25 178.2(5) . . . no
C1 C22 C23 120.2(3) . . . no
C1 C22 C20 119.9(3) . . . no
C20 C22 C23 119.9(3) . . . no
C4 C23 C22 118.9(3) . . . no
C4 C23 C6 118.3(3) . . . no
C6 C23 C22 122.8(3) . . . no
O31 C25 C103 111.0(5) . . . yes
O31 C25 C105 106.0(4) . . . yes
C21 C25 C105 111.1(5) . . . no
C103 C25 C105 110.9(5) . . . no
C21 C25 C103 110.2(5) . . . no
O31 C25 C21 107.7(4) . . . yes
C2 C1 H1 119.00 . . . no
C22 C1 H1 119.00 . . . no
C3 C5 H5 120.00 . . . no
C6 C5 H5 120.00 5_666 . . no
C23 C6 H6 119.00 . . . no
C5 C6 H6 119.00 5_666 . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
C7 C8 H8C 110.00 . . . no
H8A C8 H8B 109.00 . . . no
H8A C8 H8C 110.00 . . . no
H8B C8 H8C 109.00 . . . no
C7 C51 H51A 109.00 . . . no
C7 C51 H51B 109.00 . . . no
C7 C51 H51C 109.00 . . . no
H51A C51 H51B 109.00 . . . no
H51A C51 H51C 110.00 . . . no
H51B C51 H51C 110.00 . . . no
C25 C103 H10A 109.00 . . . no
C25 C103 H10B 109.00 . . . no
C25 C103 H10C 109.00 . . . no
H10A C103 H10B 110.00 . . . no
H10A C103 H10C 109.00 . . . no
H10B C103 H10C 109.00 . . . no
C25 C105 H10D 109.00 . . . no
C25 C105 H10E 110.00 . . . no
C25 C105 H10F 109.00 . . . no
H10D C105 H10E 110.00 . . . no
H10D C105 H10F 109.00 . . . no
H10E C105 H10F 109.00 . . . no
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
C22 C1 C2 C3 0.1(5) . . . . no
C22 C1 C2 C11 -177.9(3) . . . . no
C2 C1 C22 C20 177.1(3) . . . . no
C2 C1 C22 C23 -1.3(6) . . . . no
C1 C2 C3 C4 0.7(5) . . . . no
C1 C2 C3 C5 -179.8(3) . . . . no
C11 C2 C3 C4 178.7(3) . . . . no
C11 C2 C3 C5 -1.8(5) . . . . no
C2 C3 C4 C23 -0.3(5) . . . . no
C2 C3 C4 C4 179.0(3) . . . 5_666 no
C5 C3 C4 C23 -179.9(3) . . . . no
C5 C3 C4 C4 -0.5(4) . . . 5_666 no
C2 C3 C5 C6 -179.5(3) . . . 5_666 no
C4 C3 C5 C6 0.0(5) . . . 5_666 no
C3 C4 C23 C6 179.7(3) . . . . no
C3 C4 C23 C22 -0.8(5) . . . . no
C4 C4 C23 C6 0.3(5) 5_666 . . . no
C4 C4 C23 C22 179.9(3) 5_666 . . . no
C3 C4 C4 C3 180.0(3) . . 5_666 5_666 no
C3 C4 C4 C23 0.7(5) . . 5_666 5_666 no
C23 C4 C4 C3 -0.7(5) . . 5_666 5_666 no
C23 C4 C4 C23 -180.0(3) . . 5_666 5_666 no
C3 C5 C6 C23 0.4(6) . . 5_666 5_666 no
C5 C6 C23 C4 0.2(5) 5_666 . . . no
C5 C6 C23 C22 -179.4(4) 5_666 . . . no
C1 C22 C23 C4 1.5(5) . . . . no
C1 C22 C23 C6 -178.9(4) . . . . no
C20 C22 C23 C4 -176.8(3) . . . . no
C20 C22 C23 C6 2.8(6) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O31 O50 2.732(5) . 3_456 no
O31 O31 2.697(7) . 4_656 no
O50 O31 2.732(5) . 3_556 no
O50 O50 2.736(4) . 4_755 no
O31 H50 1.9500 . 3_456 no
O31 H31 2.2700 . 4_656 no
O50 H31 2.6800 . 3_556 no
C2 C6 3.547(5) . 4_655 no
C3 C5 3.546(5) . 8_565 no
C4 C4 3.528(4) . 4_655 no
C5 C3 3.546(5) . 8_564 no
C6 C2 3.547(5) . 4_655 no
C22 C22 3.494(5) . 4_655 no
C23 C23 3.552(5) . 4_656 no
C8 H8A 2.9100 . 8_564 no
C10 H8B 3.0200 . 8_565 no
C10 H5 3.0400 . . no
C11 H5 2.6000 . . no
C20 H6 2.5800 . . no
C21 H6 3.0400 . . no
C25 H50 3.0100 . 3_456 no
H5 C10 3.0400 . . no
H5 C11 2.6000 . . no
H6 C20 2.5800 . . no
H6 C21 3.0400 . . no
H8A C8 2.9100 . 8_565 no
H8A H8B 2.4400 . 8_565 no
H8A H8C 2.5800 . 8_565 no
H8B H51B 2.5600 . . no
H8B C10 3.0200 . 8_564 no
H8B H8A 2.4400 . 8_564 no
H8C H51A 2.4700 . . no
H8C H8C 2.5500 . 5_765 no
H8C H8A 2.5800 . 8_564 no
H10A H10F 2.3700 . . no
H10A H31 2.5300 . . no
H10B H10E 2.5700 . . no
H10C H31 2.2300 . . no
H10E H10B 2.5700 . . no
H10F H10A 2.3700 . . no
H31 H10A 2.5300 . . no
H31 H10C 2.2300 . . no
H31 O50 2.6800 . 3_456 no
H31 H50 1.9200 . 3_456 no
H31 H51C 2.5600 . 3_456 no
H31 O31 2.2700 . 4_656 no
H31 H31 2.0800 . 4_656 no
H50 H51C 2.4100 . . no
H50 O31 1.9500 . 3_556 no
H50 C25 3.0100 . 3_556 no
H50 H31 1.9200 . 3_556 no
H51A H8C 2.4700 . . no
H51B H8B 2.5600 . . no
H51C H50 2.4100 . . no
H51C H31 2.5600 . 3_556 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O31 H31 O31 0.8200 2.2700 2.697(7) 113.00 4_656 yes
O50 H50 O31 0.8200 1.9500 2.732(5) 160.00 3_556 yes
# Loop Mechanism for Extra Tables(s)
#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?
#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#===END