
data_global


data_pca2(1)
#TrackingRef 'pca2(1).cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42

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   pca2(1)

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

_cell_length_a                   23.5957(18)
_cell_length_b                   9.4893(6)
_cell_length_c                   7.7521(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1735.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1007
_cell_measurement_theta_min      2.3135
_cell_measurement_theta_max      18.581

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9890
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'ccd area detector'
_diffrn_measurement_method       'phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8362
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3859
_reflns_number_gt                1940
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker smart apexii'
_computing_cell_refinement       'bruker smart apexii'
_computing_data_reduction        'bruker saint'
_computing_structure_solution    shelxtl
_computing_structure_refinement  'shelxl-97 (sheldrick, 1997)'
_computing_molecular_graphics    wingx
_computing_publication_material  wingx

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         3859
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 0.48544(17) 0.4425(4) 0.1918(5) 0.0680(11) Uani 1 1 d . . .
H1A H 0.4821 0.5189 0.2743 0.082 Uiso 1 1 calc R . .
H1B H 0.5155 0.4653 0.1113 0.082 Uiso 1 1 calc R . .
C2 C 0.43020(18) 0.4223(4) 0.0969(5) 0.0757(12) Uani 1 1 d . . .
H2A H 0.4365 0.4270 -0.0266 0.091 Uiso 1 1 calc R . .
H2B H 0.4036 0.4958 0.1286 0.091 Uiso 1 1 calc R . .
C3 C 0.40610(15) 0.2762(3) 0.1465(4) 0.0526(9) Uani 1 1 d . . .
H3 H 0.4112 0.2082 0.0526 0.063 Uiso 1 1 calc R . .
C4 C 0.44112(14) 0.2348(3) 0.3048(4) 0.0470(8) Uani 1 1 d . . .
C5 C 0.49848(15) 0.3049(3) 0.2844(5) 0.0587(9) Uani 1 1 d . . .
H5A H 0.5157 0.3226 0.3960 0.070 Uiso 1 1 calc R . .
H5B H 0.5238 0.2467 0.2164 0.070 Uiso 1 1 calc R . .
C6 C 0.43737(14) 0.0789(3) 0.3379(4) 0.0462(8) Uani 1 1 d . . .
C7 C 0.47750(14) -0.0144(4) 0.2704(4) 0.0541(9) Uani 1 1 d . . .
H7 H 0.5085 0.0210 0.2105 0.065 Uiso 1 1 calc R . .
C8 C 0.47177(16) -0.1580(4) 0.2912(5) 0.0613(10) Uani 1 1 d . . .
H8 H 0.4991 -0.2186 0.2468 0.074 Uiso 1 1 calc R . .
C9 C 0.42591(17) -0.2117(4) 0.3770(4) 0.0595(10) Uani 1 1 d . . .
H9 H 0.4221 -0.3085 0.3917 0.071 Uiso 1 1 calc R . .
C10 C 0.38512(15) -0.1209(3) 0.4420(4) 0.0530(9) Uani 1 1 d . . .
H10 H 0.3538 -0.1579 0.4988 0.064 Uiso 1 1 calc R . .
C11 C 0.39013(14) 0.0245(3) 0.4242(4) 0.0472(8) Uani 1 1 d . . .
C12 C 0.34470(14) 0.1240(3) 0.4935(4) 0.0485(9) Uani 1 1 d . . .
H12 H 0.3076 0.0881 0.4576 0.058 Uiso 1 1 calc R . .
C13 C 0.35240(15) 0.2718(3) 0.4161(4) 0.0520(9) Uani 1 1 d . . .
C14 C 0.34581(16) 0.2719(4) 0.2162(5) 0.0600(10) Uani 1 1 d . . .
H14A H 0.3264 0.1875 0.1776 0.072 Uiso 1 1 calc R . .
H14B H 0.3246 0.3537 0.1783 0.072 Uiso 1 1 calc R . .
C15 C 0.31554(16) 0.3804(4) 0.5044(5) 0.0656(11) Uani 1 1 d . . .
H15A H 0.3264 0.4738 0.4659 0.079 Uiso 1 1 calc R . .
H15B H 0.2763 0.3652 0.4724 0.079 Uiso 1 1 calc R . .
C16 C 0.32128(18) 0.3717(4) 0.6977(5) 0.0732(13) Uani 1 1 d . . .
H16A H 0.3600 0.3932 0.7308 0.088 Uiso 1 1 calc R . .
H16B H 0.2966 0.4406 0.7514 0.088 Uiso 1 1 calc R . .
C17 C 0.34583(15) 0.1304(3) 0.6934(4) 0.0517(9) Uani 1 1 d . . .
H17 H 0.3841 0.1565 0.7305 0.062 Uiso 1 1 calc R . .
C18 C 0.32990(14) -0.0050(4) 0.7791(4) 0.0511(8) Uani 1 1 d . . .
C19 C 0.27728(17) -0.0675(4) 0.7480(4) 0.0616(10) Uani 1 1 d . . .
H19 H 0.2509 -0.0217 0.6789 0.074 Uiso 1 1 calc R . .
C20 C 0.26413(17) -0.1978(4) 0.8195(5) 0.0693(11) Uani 1 1 d . . .
H20 H 0.2291 -0.2387 0.7972 0.083 Uiso 1 1 calc R . .
C21 C 0.3025(2) -0.2663(4) 0.9227(5) 0.0729(11) Uani 1 1 d . . .
H21 H 0.2937 -0.3540 0.9692 0.088 Uiso 1 1 calc R . .
C22 C 0.35389(19) -0.2049(4) 0.9570(5) 0.0694(11) Uani 1 1 d . . .
H22 H 0.3797 -0.2503 1.0285 0.083 Uiso 1 1 calc R . .
C23 C 0.36737(16) -0.0757(4) 0.8854(5) 0.0602(10) Uani 1 1 d . . .
H23 H 0.4024 -0.0354 0.9094 0.072 Uiso 1 1 calc R . .
O1 O 0.41137(9) 0.3088(2) 0.4420(3) 0.0493(6) Uani 1 1 d . . .
O2 O 0.30676(11) 0.2345(3) 0.7564(3) 0.0653(7) Uani 1 1 d . . .


_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 C2 1.509(5) . ?
C1 C5 1.521(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.547(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.522(5) . ?
C3 C4 1.531(4) . ?
C3 H3 0.9800 . ?
C4 O1 1.455(4) . ?
C4 C6 1.504(4) . ?
C4 C5 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.398(4) . ?
C6 C11 1.398(4) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.526(4) . ?
C12 C13 1.536(4) . ?
C12 C17 1.551(4) . ?
C12 H12 0.9800 . ?
C13 O1 1.449(4) . ?
C13 C15 1.512(4) . ?
C13 C14 1.557(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.507(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.421(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.436(4) . ?
C17 C18 1.495(5) . ?
C17 H17 0.9800 . ?
C18 C23 1.382(5) . ?
C18 C19 1.397(5) . ?
C19 C20 1.389(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(5) . ?
C22 H22 0.9300 . ?
C23 H23 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
C2 C1 C5 107.2(3) . . ?
C2 C1 H1A 110.3 . . ?
C5 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C5 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C1 C2 C3 108.1(3) . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C3 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C14 C3 C4 102.3(3) . . ?
C14 C3 C2 117.1(3) . . ?
C4 C3 C2 103.3(3) . . ?
C14 C3 H3 111.1 . . ?
C4 C3 H3 111.1 . . ?
C2 C3 H3 111.1 . . ?
O1 C4 C6 108.8(3) . . ?
O1 C4 C5 107.2(3) . . ?
C6 C4 C5 120.1(3) . . ?
O1 C4 C3 101.6(2) . . ?
C6 C4 C3 110.9(3) . . ?
C5 C4 C3 106.6(3) . . ?
C1 C5 C4 104.2(3) . . ?
C1 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
C1 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C11 119.1(3) . . ?
C7 C6 C4 121.2(3) . . ?
C11 C6 C4 119.4(3) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 118.7(3) . . ?
C10 C11 C12 121.2(3) . . ?
C6 C11 C12 120.0(3) . . ?
C11 C12 C13 110.1(3) . . ?
C11 C12 C17 111.3(3) . . ?
C13 C12 C17 110.6(3) . . ?
C11 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C17 C12 H12 108.2 . . ?
O1 C13 C15 108.9(3) . . ?
O1 C13 C12 106.3(3) . . ?
C15 C13 C12 112.2(3) . . ?
O1 C13 C14 103.5(3) . . ?
C15 C13 C14 113.1(3) . . ?
C12 C13 C14 112.2(3) . . ?
C3 C14 C13 105.1(3) . . ?
C3 C14 H14A 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C3 C14 H14B 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C13 111.2(3) . . ?
C16 C15 H15A 109.4 . . ?
C13 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 C15 110.3(3) . . ?
O2 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O2 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O2 C17 C18 106.2(3) . . ?
O2 C17 C12 110.8(3) . . ?
C18 C17 C12 114.0(3) . . ?
O2 C17 H17 108.6 . . ?
C18 C17 H17 108.6 . . ?
C12 C17 H17 108.6 . . ?
C23 C18 C19 117.7(3) . . ?
C23 C18 C17 121.4(3) . . ?
C19 C18 C17 120.8(3) . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 121.5(4) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
C13 O1 C4 104.2(2) . . ?
C16 O2 C17 111.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039

data_global



# Attachment 'pccn_end.cif'


data_pccn
#TrackingRef 'pccn_end.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.40

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   pccn

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

_cell_length_a                   18.1523(18)
_cell_length_b                   18.4758(19)
_cell_length_c                   9.9808(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3347.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      3.2075
_cell_measurement_theta_max      25.5095

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14995
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3810
_reflns_number_gt                2342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0902P)²+0.4972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3810
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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 0.06901(16) 0.30378(13) 0.0906(3) 0.0746(7) Uani 1 1 d . . .
H1A H 0.0311 0.2797 0.0387 0.089 Uiso 1 1 calc R . .
H1B H 0.1168 0.2923 0.0525 0.089 Uiso 1 1 calc R . .
C2 C 0.05645(12) 0.38492(12) 0.0933(2) 0.0592(6) Uani 1 1 d . . .
H2A H 0.0046 0.3962 0.1035 0.071 Uiso 1 1 calc R . .
H2B H 0.0748 0.4076 0.0122 0.071 Uiso 1 1 calc R . .
C3 C 0.10022(10) 0.40909(10) 0.21495(19) 0.0453(5) Uani 1 1 d . . .
C4 C 0.09506(13) 0.34559(11) 0.3166(2) 0.0548(5) Uani 1 1 d . . .
H4 H 0.0607 0.3579 0.3889 0.066 Uiso 1 1 calc R . .
C5 C 0.06535(16) 0.28144(13) 0.2356(3) 0.0770(8) Uani 1 1 d . . .
H5A H 0.0952 0.2387 0.2509 0.092 Uiso 1 1 calc R . .
H5B H 0.0149 0.2708 0.2612 0.092 Uiso 1 1 calc R . .
C6 C 0.08290(10) 0.48075(10) 0.28063(19) 0.0450(5) Uani 1 1 d . . .
C7 C 0.01400(11) 0.51339(12) 0.2743(2) 0.0574(6) Uani 1 1 d . . .
H7 H -0.0231 0.4921 0.2235 0.069 Uiso 1 1 calc R . .
C8 C 0.00001(12) 0.57668(12) 0.3420(3) 0.0662(6) Uani 1 1 d . . .
H8 H -0.0463 0.5981 0.3365 0.079 Uiso 1 1 calc R . .
C9 C 0.05472(12) 0.60849(13) 0.4181(3) 0.0659(7) Uani 1 1 d . . .
H9 H 0.0454 0.6515 0.4633 0.079 Uiso 1 1 calc R . .
C10 C 0.13810(10) 0.51234(10) 0.35973(19) 0.0437(5) Uani 1 1 d . . .
C11 C 0.21260(10) 0.47645(10) 0.37069(19) 0.0429(4) Uani 1 1 d . . .
H11 H 0.2257 0.4714 0.4655 0.051 Uiso 1 1 calc R . .
C12 C 0.17324(14) 0.33998(12) 0.3714(2) 0.0651(6) Uani 1 1 d . . .
H12A H 0.1951 0.2937 0.3486 0.078 Uiso 1 1 calc R . .
H12B H 0.1736 0.3455 0.4681 0.078 Uiso 1 1 calc R . .
C13 C 0.21487(11) 0.40206(10) 0.30388(19) 0.0473(5) Uani 1 1 d . . .
C14 C 0.29627(12) 0.39087(13) 0.2811(3) 0.0642(6) Uani 1 1 d . . .
H14A H 0.3167 0.3611 0.3520 0.077 Uiso 1 1 calc R . .
H14B H 0.3044 0.3666 0.1962 0.077 Uiso 1 1 calc R . .
C15 C 0.27541(10) 0.51482(11) 0.29658(19) 0.0486(5) Uani 1 1 d . . .
H15 H 0.2578 0.5293 0.2077 0.058 Uiso 1 1 calc R . .
C16 C 0.30891(10) 0.57958(11) 0.3639(2) 0.0476(5) Uani 1 1 d . . .
C17 C 0.34149(11) 0.57329(12) 0.4889(2) 0.0542(5) Uani 1 1 d . . .
H17 H 0.3447 0.5281 0.5295 0.065 Uiso 1 1 calc R . .
C18 C 0.36933(13) 0.63344(13) 0.5542(2) 0.0641(6) Uani 1 1 d . . .
H18 H 0.3908 0.6284 0.6383 0.077 Uiso 1 1 calc R . .
C19 C 0.36544(14) 0.70055(14) 0.4955(3) 0.0707(7) Uani 1 1 d . . .
H19 H 0.3830 0.7412 0.5403 0.085 Uiso 1 1 calc R . .
C20 C 0.33526(16) 0.70688(14) 0.3697(3) 0.0787(8) Uani 1 1 d . . .
H20 H 0.3339 0.7519 0.3282 0.094 Uiso 1 1 calc R . .
C21 C 0.30693(14) 0.64721(13) 0.3041(3) 0.0665(6) Uani 1 1 d . . .
H21 H 0.2864 0.6525 0.2192 0.080 Uiso 1 1 calc R . .
C22 C 0.12329(11) 0.57632(11) 0.4271(2) 0.0544(5) Uani 1 1 d . . .
H22 H 0.1599 0.5978 0.4788 0.065 Uiso 1 1 calc R . .
O1 O 0.17744(7) 0.40885(7) 0.17759(12) 0.0458(4) Uani 1 1 d . . .
O2 O 0.33077(8) 0.45967(9) 0.28041(18) 0.0691(5) Uani 1 1 d . . .


_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 C5 1.506(4) . ?
C1 C2 1.517(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.451(2) . ?
C3 C6 1.510(3) . ?
C3 C4 1.554(3) . ?
C4 C12 1.524(3) . ?
C4 C5 1.533(3) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.390(3) . ?
C6 C10 1.403(3) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C22 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C22 1.386(3) . ?
C10 C11 1.510(3) . ?
C11 C13 1.528(3) . ?
C11 C15 1.533(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.530(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.437(2) . ?
C13 C14 1.509(3) . ?
C14 O2 1.417(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.440(2) . ?
C15 C16 1.501(3) . ?
C15 H15 0.9800 . ?
C16 C21 1.385(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 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 C1 C2 104.32(19) . . ?
C5 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
C5 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C1 C2 C3 103.07(18) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
O1 C3 C6 108.39(15) . . ?
O1 C3 C2 107.41(16) . . ?
C6 C3 C2 119.74(17) . . ?
O1 C3 C4 102.93(15) . . ?
C6 C3 C4 111.46(16) . . ?
C2 C3 C4 105.58(17) . . ?
C12 C4 C5 117.7(2) . . ?
C12 C4 C3 103.27(17) . . ?
C5 C4 C3 105.10(17) . . ?
C12 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C1 C5 C4 106.23(19) . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C7 C6 C10 119.21(19) . . ?
C7 C6 C3 123.21(18) . . ?
C10 C6 C3 117.40(17) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C22 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C22 C9 H9 120.0 . . ?
C22 C10 C6 119.30(18) . . ?
C22 C10 C11 120.86(17) . . ?
C6 C10 C11 119.85(17) . . ?
C10 C11 C13 112.80(16) . . ?
C10 C11 C15 115.34(15) . . ?
C13 C11 C15 100.68(15) . . ?
C10 C11 H11 109.2 . . ?
C13 C11 H11 109.2 . . ?
C15 C11 H11 109.2 . . ?
C4 C12 C13 104.52(17) . . ?
C4 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C4 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
O1 C13 C14 110.04(17) . . ?
O1 C13 C11 106.95(14) . . ?
C14 C13 C11 102.43(17) . . ?
O1 C13 C12 102.62(16) . . ?
C14 C13 C12 116.56(18) . . ?
C11 C13 C12 117.95(18) . . ?
O2 C14 C13 108.10(17) . . ?
O2 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O2 C15 C16 109.35(16) . . ?
O2 C15 C11 104.24(16) . . ?
C16 C15 C11 117.01(16) . . ?
O2 C15 H15 108.7 . . ?
C16 C15 H15 108.7 . . ?
C11 C15 H15 108.7 . . ?
C21 C16 C17 118.4(2) . . ?
C21 C16 C15 121.0(2) . . ?
C17 C16 C15 120.60(18) . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.1(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.9(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C9 C22 C10 120.6(2) . . ?
C9 C22 H22 119.7 . . ?
C10 C22 H22 119.7 . . ?
C13 O1 C3 103.39(14) . . ?
C14 O2 C15 109.00(16) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067


