# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 1412785'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2016-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/N

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

_cell_length_a                   5.3480(11)
_cell_length_b                   12.242(2)
_cell_length_c                   17.786(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.89(3)
_cell_angle_gamma                90.00
_cell_volume                     1161.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2386
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2147
_reflns_number_gt                1221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2800P] 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         2147
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0869(4) 0.8585(2) 0.55032(13) 0.0585(7) Uani 1 1 d . . .
C2 C 0.0546(6) 0.6756(3) 0.51910(18) 0.0520(9) Uani 1 1 d . . .
H2A H 0.2208 0.7071 0.5186 0.062 Uiso 1 1 calc R . .
H2B H 0.0322 0.6257 0.4768 0.062 Uiso 1 1 calc R . .
O2 O -0.3282(5) 0.7607(3) 0.47200(15) 0.0756(9) Uani 1 1 d . . .
C3 C -0.1361(6) 0.7643(3) 0.51031(19) 0.0525(9) Uani 1 1 d . . .
C4 C 0.1172(6) 0.8648(3) 0.60441(18) 0.0465(8) Uani 1 1 d . . .
C5 C 0.2671(7) 0.9578(3) 0.6001(2) 0.0580(10) Uani 1 1 d . . .
H5A H 0.2348 1.0088 0.5620 0.070 Uiso 1 1 calc R . .
C6 C 0.4610(7) 0.9723(3) 0.6527(2) 0.0572(10) Uani 1 1 d . . .
H6A H 0.5623 1.0337 0.6501 0.069 Uiso 1 1 calc R . .
C7 C 0.5108(6) 0.8958(3) 0.71098(19) 0.0474(9) Uani 1 1 d . . .
C8 C 0.7157(6) 0.9090(3) 0.7647(2) 0.0591(10) Uani 1 1 d . . .
H8A H 0.8192 0.9697 0.7616 0.071 Uiso 1 1 calc R . .
C9 C 0.7648(7) 0.8352(3) 0.8206(2) 0.0623(11) Uani 1 1 d . . .
H9A H 0.9013 0.8450 0.8551 0.075 Uiso 1 1 calc R . .
C10 C 0.6091(7) 0.7445(3) 0.82590(19) 0.0586(10) Uani 1 1 d . . .
H10A H 0.6417 0.6945 0.8647 0.070 Uiso 1 1 calc R . .
C12 C 0.3556(6) 0.8029(3) 0.71502(17) 0.0420(8) Uani 1 1 d . . .
C11 C 0.4098(6) 0.7280(3) 0.77515(18) 0.0502(9) Uani 1 1 d . . .
H11A H 0.3081 0.6671 0.7799 0.060 Uiso 1 1 calc R . .
C13 C 0.1515(6) 0.7876(3) 0.65937(17) 0.0415(8) Uani 1 1 d . . .
C14 C -0.0197(6) 0.6898(3) 0.65727(18) 0.0467(8) Uani 1 1 d . . .
H14A H -0.1924 0.7142 0.6511 0.056 Uiso 1 1 calc R . .
H14B H 0.0023 0.6509 0.7048 0.056 Uiso 1 1 calc R . .
C1 C 0.0343(6) 0.6119(3) 0.59246(17) 0.0445(8) Uani 1 1 d . . .
H1A H -0.1080 0.5617 0.5851 0.053 Uiso 1 1 calc R . .
C15 C 0.2693(7) 0.5437(3) 0.6101(2) 0.0592(10) Uani 1 1 d . . .
H15A H 0.2957 0.4964 0.5682 0.089 Uiso 1 1 calc R . .
H15B H 0.2492 0.5004 0.6543 0.089 Uiso 1 1 calc R . .
H15C H 0.4113 0.5911 0.6187 0.089 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0572(15) 0.0568(16) 0.0599(15) 0.0006(13) -0.0083(12) 0.0082(12)
C2 0.050(2) 0.064(2) 0.0425(19) -0.0097(17) 0.0074(16) -0.0092(18)
O2 0.0544(16) 0.105(2) 0.0650(17) 0.0006(16) -0.0163(14) -0.0041(15)
C3 0.047(2) 0.067(3) 0.0437(19) 0.0045(18) 0.0026(17) -0.0083(18)
C4 0.0444(19) 0.049(2) 0.0463(19) -0.0040(16) 0.0018(15) 0.0030(16)
C5 0.072(2) 0.043(2) 0.059(2) 0.0049(17) 0.005(2) 0.0014(19)
C6 0.059(2) 0.044(2) 0.068(2) -0.0064(19) 0.010(2) -0.0132(18)
C7 0.0485(19) 0.047(2) 0.048(2) -0.0154(16) 0.0080(16) 0.0003(17)
C8 0.048(2) 0.063(2) 0.067(3) -0.024(2) 0.0051(19) -0.0050(18)
C9 0.052(2) 0.082(3) 0.052(2) -0.022(2) -0.0069(18) 0.007(2)
C10 0.059(2) 0.077(3) 0.0387(19) -0.0109(19) 0.0025(17) 0.016(2)
C12 0.0397(17) 0.049(2) 0.0380(17) -0.0071(15) 0.0093(14) 0.0052(15)
C11 0.054(2) 0.059(2) 0.0385(18) -0.0046(16) 0.0085(16) 0.0013(17)
C13 0.0402(17) 0.0422(18) 0.0432(18) -0.0020(15) 0.0105(14) -0.0009(14)
C14 0.0435(18) 0.053(2) 0.0443(19) -0.0016(16) 0.0073(15) -0.0027(16)
C1 0.0369(17) 0.0460(19) 0.051(2) -0.0042(15) 0.0065(15) -0.0083(15)
C15 0.052(2) 0.055(2) 0.070(2) -0.0065(19) 0.0010(19) 0.0025(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.371(4) . ?
O1 C4 1.407(4) . ?
C2 C3 1.491(5) . ?
C2 C1 1.530(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O2 C3 1.195(4) . ?
C4 C13 1.363(4) . ?
C4 C5 1.397(5) . ?
C5 C6 1.360(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.409(5) . ?
C6 H6A 0.9300 . ?
C7 C12 1.413(4) . ?
C7 C8 1.413(5) . ?
C8 C9 1.356(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.395(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10A 0.9300 . ?
C12 C11 1.424(4) . ?
C12 C13 1.435(4) . ?
C11 H11A 0.9300 . ?
C13 C14 1.506(4) . ?
C14 C1 1.538(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C15 1.524(4) . ?
C1 H1A 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C4 120.9(3) . . ?
C3 C2 C1 111.9(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O2 C3 O1 117.0(4) . . ?
O2 C3 C2 126.0(4) . . ?
O1 C3 C2 116.9(3) . . ?
C13 C4 C5 123.7(3) . . ?
C13 C4 O1 120.8(3) . . ?
C5 C4 O1 115.4(3) . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C12 119.3(3) . . ?
C6 C7 C8 121.4(3) . . ?
C12 C7 C8 119.3(3) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C7 C12 C11 117.8(3) . . ?
C7 C12 C13 119.5(3) . . ?
C11 C12 C13 122.7(3) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C4 C13 C12 117.5(3) . . ?
C4 C13 C14 118.8(3) . . ?
C12 C13 C14 123.6(3) . . ?
C13 C14 C1 111.5(3) . . ?
C13 C14 H14A 109.3 . . ?
C1 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C1 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C1 C2 110.4(3) . . ?
C15 C1 C14 112.3(3) . . ?
C2 C1 C14 110.5(3) . . ?
C15 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
C14 C1 H1A 107.8 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C3 O2 171.4(3) . . . . ?
C4 O1 C3 C2 -8.2(5) . . . . ?
C1 C2 C3 O2 -100.7(4) . . . . ?
C1 C2 C3 O1 78.8(4) . . . . ?
C3 O1 C4 C13 -51.1(4) . . . . ?
C3 O1 C4 C5 132.9(3) . . . . ?
C13 C4 C5 C6 1.0(5) . . . . ?
O1 C4 C5 C6 176.9(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C12 -0.4(5) . . . . ?
C5 C6 C7 C8 178.4(3) . . . . ?
C6 C7 C8 C9 -179.6(3) . . . . ?
C12 C7 C8 C9 -0.9(5) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 0.9(5) . . . . ?
C6 C7 C12 C11 -179.3(3) . . . . ?
C8 C7 C12 C11 1.9(4) . . . . ?
C6 C7 C12 C13 0.5(4) . . . . ?
C8 C7 C12 C13 -178.3(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C7 C12 C11 C10 -1.6(5) . . . . ?
C13 C12 C11 C10 178.6(3) . . . . ?
C5 C4 C13 C12 -0.8(5) . . . . ?
O1 C4 C13 C12 -176.5(3) . . . . ?
C5 C4 C13 C14 -179.0(3) . . . . ?
O1 C4 C13 C14 5.3(4) . . . . ?
C7 C12 C13 C4 0.0(4) . . . . ?
C11 C12 C13 C4 179.9(3) . . . . ?
C7 C12 C13 C14 178.1(3) . . . . ?
C11 C12 C13 C14 -2.1(5) . . . . ?
C4 C13 C14 C1 71.3(4) . . . . ?
C12 C13 C14 C1 -106.7(3) . . . . ?
C3 C2 C1 C15 -164.9(3) . . . . ?
C3 C2 C1 C14 -40.0(4) . . . . ?
C13 C14 C1 C15 76.5(3) . . . . ?
C13 C14 C1 C2 -47.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 1432822'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3630(15)
_cell_length_b                   17.941(4)
_cell_length_c                   8.5680(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.50(3)
_cell_angle_gamma                90.00
_cell_volume                     1131.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2245
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_sigmaI/netI    0.1205
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.37
_reflns_number_total             1622
_reflns_number_gt                641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0380P)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_number_reflns         1622
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1981
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.3623(6) 0.1785(3) 0.9870(5) 0.1089(18) Uani 1 1 d . . .
C1 C 1.2805(9) 0.1574(4) 1.2454(7) 0.102(2) Uani 1 1 d . . .
H1A H 1.3938 0.1824 1.2659 0.153 Uiso 1 1 calc R . .
H1B H 1.2871 0.1075 1.2861 0.153 Uiso 1 1 calc R . .
H1C H 1.1845 0.1839 1.2948 0.153 Uiso 1 1 calc R . .
O2 O 0.6065(5) 0.0320(2) 0.8067(5) 0.0702(12) Uani 1 1 d . . .
C2 C 1.2432(9) 0.1546(4) 1.0741(7) 0.0728(19) Uani 1 1 d . . .
O3 O 0.3727(5) 0.0321(2) 0.6383(4) 0.0876(15) Uani 1 1 d . . .
C3 C 1.0790(7) 0.1220(3) 1.0046(7) 0.0538(15) Uani 1 1 d . . .
C4 C 0.9451(8) 0.0931(3) 1.0953(6) 0.0615(17) Uani 1 1 d . . .
H4A H 0.9622 0.0922 1.2032 0.074 Uiso 1 1 calc R . .
C5 C 0.7836(8) 0.0648(3) 1.0295(7) 0.0628(17) Uani 1 1 d . . .
H5A H 0.6922 0.0464 1.0916 0.075 Uiso 1 1 calc R . .
C6 C 0.7651(8) 0.0653(3) 0.8700(7) 0.0543(15) Uani 1 1 d . . .
C7 C 0.4998(8) 0.0660(4) 0.6909(7) 0.0650(18) Uani 1 1 d . . .
C8 C 0.5577(6) 0.1417(3) 0.6434(6) 0.0599(16) Uani 1 1 d . . .
H8A H 0.5889 0.1704 0.7362 0.072 Uiso 1 1 calc R . .
H8B H 0.4565 0.1665 0.5903 0.072 Uiso 1 1 calc R . .
C9 C 0.7213(8) 0.1412(4) 0.5354(7) 0.0716(18) Uani 1 1 d . . .
H9A H 0.6799 0.1238 0.4321 0.086 Uiso 1 1 calc R . .
C10 C 0.8687(7) 0.0874(3) 0.5980(6) 0.0621(16) Uani 1 1 d U . .
H10A H 0.8351 0.0369 0.5690 0.075 Uiso 1 1 calc R . .
H10B H 0.9824 0.0989 0.5486 0.075 Uiso 1 1 calc R . .
C11 C 0.8972(8) 0.0910(3) 0.7708(6) 0.0491(14) Uani 1 1 d U . .
C12 C 1.0511(7) 0.1205(3) 0.8432(6) 0.0546(15) Uani 1 1 d . . .
H12A H 1.1407 0.1404 0.7809 0.066 Uiso 1 1 calc R . .
C13 C 0.7971(8) 0.2161(3) 0.5190(8) 0.111(3) Uani 1 1 d . . .
H13A H 0.7041 0.2494 0.4807 0.167 Uiso 1 1 calc R . .
H13B H 0.8945 0.2148 0.4467 0.167 Uiso 1 1 calc R . .
H13C H 0.8425 0.2333 0.6187 0.167 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.087(3) 0.160(5) 0.080(3) 0.007(3) -0.002(3) -0.040(3)
C1 0.129(7) 0.111(6) 0.066(5) 0.010(5) -0.007(4) -0.012(5)
O2 0.079(3) 0.058(3) 0.074(3) 0.005(2) 0.012(2) -0.009(2)
C2 0.076(5) 0.072(5) 0.071(5) 0.007(4) 0.018(4) -0.002(4)
O3 0.072(3) 0.107(4) 0.084(3) -0.019(3) -0.003(2) -0.023(3)
C3 0.052(4) 0.044(3) 0.066(4) 0.001(3) 0.015(3) -0.005(3)
C4 0.063(4) 0.060(4) 0.061(4) 0.008(3) 0.003(3) 0.005(3)
C5 0.080(5) 0.055(4) 0.054(4) 0.017(3) 0.024(3) 0.007(4)
C6 0.061(4) 0.034(3) 0.069(4) -0.005(3) -0.003(3) -0.001(3)
C7 0.065(5) 0.079(5) 0.053(4) -0.016(4) 0.027(3) -0.021(4)
C8 0.047(4) 0.069(4) 0.064(4) 0.008(3) 0.016(3) -0.006(3)
C9 0.078(5) 0.070(5) 0.068(4) -0.004(4) 0.019(3) -0.031(4)
C10 0.059(4) 0.064(4) 0.064(4) -0.005(3) 0.016(3) -0.003(3)
C11 0.061(4) 0.049(4) 0.038(3) -0.002(3) 0.012(3) 0.009(3)
C12 0.060(4) 0.050(4) 0.054(4) 0.003(3) 0.009(3) 0.005(3)
C13 0.115(6) 0.074(5) 0.147(7) 0.029(5) 0.036(5) -0.003(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.243(6) . ?
C1 C2 1.487(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C7 1.390(6) . ?
O2 C6 1.407(6) . ?
C2 C3 1.455(7) . ?
O3 C7 1.194(6) . ?
C3 C4 1.374(6) . ?
C3 C12 1.392(6) . ?
C4 C5 1.397(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.370(7) . ?
C5 H5A 0.9300 . ?
C6 C11 1.387(7) . ?
C7 C8 1.484(7) . ?
C8 C9 1.538(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.464(7) . ?
C9 C10 1.539(7) . ?
C9 H9A 0.9800 . ?
C10 C11 1.491(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.383(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 O2 C6 122.5(5) . . ?
O1 C2 C3 119.0(6) . . ?
O1 C2 C1 117.8(6) . . ?
C3 C2 C1 123.2(6) . . ?
C4 C3 C12 117.7(6) . . ?
C4 C3 C2 121.4(6) . . ?
C12 C3 C2 120.9(5) . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 H5A 121.2 . . ?
C4 C5 H5A 121.2 . . ?
C5 C6 C11 124.1(5) . . ?
C5 C6 O2 116.2(5) . . ?
C11 C6 O2 119.5(5) . . ?
O3 C7 O2 118.0(6) . . ?
O3 C7 C8 126.2(6) . . ?
O2 C7 C8 115.8(5) . . ?
C7 C8 C9 113.2(5) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C13 C9 C8 111.0(5) . . ?
C13 C9 C10 110.0(5) . . ?
C8 C9 C10 110.5(5) . . ?
C13 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C11 C10 C9 113.5(5) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C6 115.6(5) . . ?
C12 C11 C10 123.7(5) . . ?
C6 C11 C10 120.8(5) . . ?
C11 C12 C3 123.4(5) . . ?
C11 C12 H12A 118.3 . . ?
C3 C12 H12A 118.3 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.4(6) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
O1 C2 C3 C12 -2.8(9) . . . . ?
C1 C2 C3 C12 -179.7(6) . . . . ?
C12 C3 C4 C5 -1.8(8) . . . . ?
C2 C3 C4 C5 177.1(6) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C5 C6 C11 1.0(8) . . . . ?
C4 C5 C6 O2 175.9(5) . . . . ?
C7 O2 C6 C5 133.1(5) . . . . ?
C7 O2 C6 C11 -51.7(7) . . . . ?
C6 O2 C7 O3 176.3(5) . . . . ?
C6 O2 C7 C8 -3.1(7) . . . . ?
O3 C7 C8 C9 -102.1(7) . . . . ?
O2 C7 C8 C9 77.3(6) . . . . ?
C7 C8 C9 C13 -167.9(5) . . . . ?
C7 C8 C9 C10 -45.5(6) . . . . ?
C13 C9 C10 C11 81.7(6) . . . . ?
C8 C9 C10 C11 -41.3(6) . . . . ?
C5 C6 C11 C12 -3.1(8) . . . . ?
O2 C6 C11 C12 -177.9(5) . . . . ?
C5 C6 C11 C10 178.0(5) . . . . ?
O2 C6 C11 C10 3.3(8) . . . . ?
C9 C10 C11 C12 -109.7(6) . . . . ?
C9 C10 C11 C6 69.0(7) . . . . ?
C6 C11 C12 C3 2.9(8) . . . . ?
C10 C11 C12 C3 -178.3(5) . . . . ?
C4 C3 C12 C11 -0.5(8) . . . . ?
C2 C3 C12 C11 -179.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.044
