# 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_AAB_AJ_60_0m
_database_code_depnum_ccdc_archive 'CCDC 1451380'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   14.6923(14)
_cell_length_b                   5.7956(6)
_cell_length_c                   18.3537(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.638(7)
_cell_angle_gamma                90
_cell_volume                     1518.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2480
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.25

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'BRUKER 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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8929
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.603
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2627
_reflns_number_gt                1888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.16416(10) 0.2494(3) 0.25025(8) 0.0511(4) Uani 1 1 d . . . . .
O2 O 0.93746(11) 1.0345(3) 0.19905(9) 0.0556(4) Uani 1 1 d . . . . .
O3 O 1.13906(12) 0.4374(3) 0.02793(8) 0.0587(5) Uani 1 1 d . . . . .
O4 O 1.09331(10) 0.7874(2) 0.05502(7) 0.0448(4) Uani 1 1 d . . . . .
C1 C 1.06542(13) 0.6723(3) 0.19353(10) 0.0347(5) Uani 1 1 d . . . . .
H1 H 1.0826 0.8322 0.1857 0.042 Uiso 1 1 calc R U . . .
C2 C 1.11412(13) 0.5148(3) 0.14958(10) 0.0345(5) Uani 1 1 d . . . . .
C3 C 1.15516(14) 0.3204(4) 0.17853(11) 0.0430(5) Uani 1 1 d . . . . .
H3 H 1.1797 0.2254 0.1471 0.052 Uiso 1 1 calc R U . . .
C4 C 1.14121(13) 0.4088(4) 0.29986(11) 0.0425(5) Uani 1 1 d . . . . .
C5 C 1.09730(13) 0.6154(4) 0.27623(11) 0.0378(5) Uani 1 1 d . . . . .
C6 C 1.08251(15) 0.7658(4) 0.33117(11) 0.0501(6) Uani 1 1 d . . . . .
H6 H 1.0546 0.9080 0.3171 0.060 Uiso 1 1 calc R U . . .
C7 C 1.10839(18) 0.7087(5) 0.40624(12) 0.0630(7) Uani 1 1 d . . . . .
H7 H 1.0976 0.8119 0.4421 0.076 Uiso 1 1 calc R U . . .
C8 C 1.15012(17) 0.4990(5) 0.42812(13) 0.0630(7) Uani 1 1 d . . . . .
H8 H 1.1667 0.4594 0.4786 0.076 Uiso 1 1 calc R U . . .
C9 C 1.16707(15) 0.3486(4) 0.37491(12) 0.0535(6) Uani 1 1 d . . . . .
H9 H 1.1957 0.2073 0.3892 0.064 Uiso 1 1 calc R U . . .
C10 C 0.95896(13) 0.6452(3) 0.16477(10) 0.0358(5) Uani 1 1 d . . . . .
H10A H 0.9455 0.6122 0.1115 0.043 Uiso 1 1 calc R U . . .
H10B H 0.9390 0.5127 0.1893 0.043 Uiso 1 1 calc R U . . .
C11 C 0.90139(14) 0.8508(4) 0.17686(10) 0.0384(5) Uani 1 1 d . . . . .
C12 C 0.79733(14) 0.8253(4) 0.15859(10) 0.0402(5) Uani 1 1 d . . . . .
C13 C 0.75180(15) 0.6312(4) 0.12375(12) 0.0513(6) Uani 1 1 d . . . . .
H13 H 0.7865 0.5108 0.1105 0.062 Uiso 1 1 calc R U . . .
C14 C 0.65510(16) 0.6149(5) 0.10852(14) 0.0644(7) Uani 1 1 d . . . . .
H14 H 0.6249 0.4845 0.0849 0.077 Uiso 1 1 calc R U . . .
C15 C 0.60387(17) 0.7929(6) 0.12857(14) 0.0689(8) Uani 1 1 d . . . . .
H15 H 0.5390 0.7818 0.1189 0.083 Uiso 1 1 calc R U . . .
C16 C 0.64818(18) 0.9870(5) 0.16278(15) 0.0674(8) Uani 1 1 d . . . . .
H16 H 0.6132 1.1072 0.1759 0.081 Uiso 1 1 calc R U . . .
C17 C 0.74422(16) 1.0033(4) 0.17763(12) 0.0532(6) Uani 1 1 d . . . . .
H17 H 0.7738 1.1351 0.2007 0.064 Uiso 1 1 calc R U . . .
C18 C 1.11693(13) 0.5673(3) 0.07200(11) 0.0373(5) Uani 1 1 d . . . . .
C19 C 1.09673(17) 0.8642(4) -0.01913(11) 0.0540(6) Uani 1 1 d . . . . .
H19A H 1.1543 0.8142 -0.0301 0.081 Uiso 1 1 calc R U . . .
H19B H 1.0933 1.0296 -0.0213 0.081 Uiso 1 1 calc R U . . .
H19C H 1.0448 0.7999 -0.0553 0.081 Uiso 1 1 calc R U . . .


_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 1.356(2) . ?
O1 C4 1.393(2) . ?
O2 C11 1.216(2) . ?
O3 C18 1.204(2) . ?
O4 C18 1.340(2) . ?
O4 C19 1.444(2) . ?
C1 C2 1.506(3) . ?
C1 C5 1.516(3) . ?
C1 C10 1.536(3) . ?
C2 C3 1.328(3) . ?
C2 C18 1.466(3) . ?
C4 C5 1.380(3) . ?
C4 C9 1.384(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.380(3) . ?
C7 C8 1.378(4) . ?
C8 C9 1.375(3) . ?
C10 C11 1.508(3) . ?
C11 C12 1.493(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.387(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.376(3) . ?

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 116.76(16) . . ?
C18 O4 C19 116.63(16) . . ?
C2 C1 C5 109.31(16) . . ?
C2 C1 C10 109.12(15) . . ?
C5 C1 C10 111.77(15) . . ?
C3 C2 C18 116.77(18) . . ?
C3 C2 C1 121.89(18) . . ?
C18 C2 C1 121.33(16) . . ?
C2 C3 O1 125.24(19) . . ?
C5 C4 C9 122.0(2) . . ?
C5 C4 O1 122.48(18) . . ?
C9 C4 O1 115.5(2) . . ?
C4 C5 C6 117.26(19) . . ?
C4 C5 C1 120.98(18) . . ?
C6 C5 C1 121.75(19) . . ?
C7 C6 C5 121.4(2) . . ?
C8 C7 C6 120.1(2) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C4 119.6(2) . . ?
C11 C10 C1 115.44(16) . . ?
O2 C11 C12 120.27(19) . . ?
O2 C11 C10 121.74(19) . . ?
C12 C11 C10 117.97(18) . . ?
C13 C12 C17 118.8(2) . . ?
C13 C12 C11 122.77(19) . . ?
C17 C12 C11 118.5(2) . . ?
C14 C13 C12 120.6(2) . . ?
C15 C14 C13 119.6(3) . . ?
C16 C15 C14 120.3(2) . . ?
C15 C16 C17 120.0(2) . . ?
C16 C17 C12 120.7(2) . . ?
O3 C18 O4 122.34(18) . . ?
O3 C18 C2 126.63(19) . . ?
O4 C18 C2 111.01(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 17.5(2) . . . . ?
C10 C1 C2 C3 -105.0(2) . . . . ?
C5 C1 C2 C18 -163.55(16) . . . . ?
C10 C1 C2 C18 74.0(2) . . . . ?
C18 C2 C3 O1 176.19(17) . . . . ?
C1 C2 C3 O1 -4.9(3) . . . . ?
C4 O1 C3 C2 -10.2(3) . . . . ?
C3 O1 C4 C5 10.2(3) . . . . ?
C3 O1 C4 C9 -168.56(17) . . . . ?
C9 C4 C5 C6 2.1(3) . . . . ?
O1 C4 C5 C6 -176.61(17) . . . . ?
C9 C4 C5 C1 -176.99(18) . . . . ?
O1 C4 C5 C1 4.3(3) . . . . ?
C2 C1 C5 C4 -17.0(2) . . . . ?
C10 C1 C5 C4 103.9(2) . . . . ?
C2 C1 C5 C6 163.94(18) . . . . ?
C10 C1 C5 C6 -75.2(2) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C1 C5 C6 C7 177.4(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 C4 -0.6(3) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
O1 C4 C9 C8 177.79(19) . . . . ?
C2 C1 C10 C11 -154.66(16) . . . . ?
C5 C1 C10 C11 84.3(2) . . . . ?
C1 C10 C11 O2 9.0(3) . . . . ?
C1 C10 C11 C12 -172.80(16) . . . . ?
O2 C11 C12 C13 171.06(19) . . . . ?
C10 C11 C12 C13 -7.2(3) . . . . ?
O2 C11 C12 C17 -9.2(3) . . . . ?
C10 C11 C12 C17 172.55(17) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 179.47(19) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C11 C12 C17 C16 -179.2(2) . . . . ?
C19 O4 C18 O3 -0.8(3) . . . . ?
C19 O4 C18 C2 177.73(17) . . . . ?
C3 C2 C18 O3 12.7(3) . . . . ?
C1 C2 C18 O3 -166.27(19) . . . . ?
C3 C2 C18 O4 -165.73(17) . . . . ?
C1 C2 C18 O4 15.3(2) . . . . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_ABB_AK_52_0m
_database_code_depnum_ccdc_archive 'CCDC 1451381'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0700(10)
_cell_length_b                   21.309(3)
_cell_length_c                   14.389(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.273(2)
_cell_angle_gamma                90
_cell_volume                     1858.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8444
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14303
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3271
_reflns_number_gt                2945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.6266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3271
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93710(15) 1.06349(4) 0.07299(7) 0.0321(2) Uani 1 1 d . . . . .
O2 O 0.84557(16) 1.05907(5) 0.29905(7) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.31578(15) 0.94518(5) 0.14166(8) 0.0387(3) Uani 1 1 d . . . . .
C1 C 0.5072(2) 1.06599(6) 0.15471(9) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.3614 1.0658 0.1186 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6291(2) 1.00739(6) 0.12794(9) 0.0246(3) Uani 1 1 d . . . . .
C3 C 0.8254(2) 1.01016(6) 0.09085(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.8925 0.9715 0.0757 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8337(2) 1.12033(6) 0.08758(9) 0.0289(3) Uani 1 1 d . . . . .
C5 C 0.6297(2) 1.12413(6) 0.12606(9) 0.0281(3) Uani 1 1 d . . . . .
C6 C 0.5421(3) 1.18397(7) 0.13645(10) 0.0370(3) Uani 1 1 d . . . . .
H6 H 0.4023 1.1884 0.1622 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6535(3) 1.23705(7) 0.11017(12) 0.0464(4) Uani 1 1 d . . . . .
H7 H 0.5906 1.2774 0.1184 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8566(3) 1.23151(7) 0.07188(11) 0.0459(4) Uani 1 1 d . . . . .
H8 H 0.9333 1.2680 0.0538 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9472(3) 1.17296(7) 0.05996(10) 0.0375(3) Uani 1 1 d . . . . .
H9 H 1.0859 1.1687 0.0331 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4596(2) 1.06727(6) 0.25866(10) 0.0292(3) Uani 1 1 d . . . . .
H10A H 0.3727 1.1054 0.2707 0.035 Uiso 1 1 calc R U . . .
H10B H 0.3666 1.0306 0.2721 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6604(2) 1.06651(6) 0.32561(10) 0.0288(3) Uani 1 1 d . . . . .
C12 C 0.6270(2) 1.07504(6) 0.42727(9) 0.0299(3) Uani 1 1 d . . . . .
C13 C 0.8060(3) 1.06643(8) 0.48991(11) 0.0444(4) Uani 1 1 d . . . . .
H13 H 0.9452 1.0552 0.4679 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7837(3) 1.07400(9) 0.58442(12) 0.0558(5) Uani 1 1 d . . . . .
H14 H 0.9072 1.0673 0.6268 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5848(3) 1.09102(8) 0.61732(11) 0.0489(4) Uani 1 1 d . . . . .
H15 H 0.5708 1.0968 0.6822 0.059 Uiso 1 1 calc R U . . .
C16 C 0.4064(3) 1.09958(8) 0.55609(12) 0.0497(4) Uani 1 1 d . . . . .
H16 H 0.2683 1.1114 0.5786 0.060 Uiso 1 1 calc R U . . .
C17 C 0.4258(3) 1.09109(8) 0.46150(11) 0.0414(4) Uani 1 1 d . . . . .
H17 H 0.3002 1.0963 0.4197 0.050 Uiso 1 1 calc R U . . .
C18 C 0.5173(2) 0.94678(6) 0.13765(9) 0.0266(3) Uani 1 1 d . . . . .
C19 C 0.6457(2) 0.88686(6) 0.14620(9) 0.0255(3) Uani 1 1 d . . . . .
C20 C 0.8558(2) 0.88372(6) 0.19042(9) 0.0291(3) Uani 1 1 d . . . . .
H20 H 0.9247 0.9209 0.2142 0.035 Uiso 1 1 calc R U . . .
C21 C 0.9647(2) 0.82681(6) 0.19991(10) 0.0320(3) Uani 1 1 d . . . . .
H21 H 1.1071 0.8255 0.2309 0.038 Uiso 1 1 calc R U . . .
C22 C 0.8703(2) 0.77166(6) 0.16519(10) 0.0311(3) Uani 1 1 d . . . . .
C23 C 0.6588(2) 0.77501(6) 0.12227(10) 0.0330(3) Uani 1 1 d . . . . .
H23 H 0.5902 0.7378 0.0986 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5473(2) 0.83127(6) 0.11341(9) 0.0302(3) Uani 1 1 d . . . . .
H24 H 0.4023 0.8322 0.0848 0.036 Uiso 1 1 calc R U . . .
C25 C 0.9951(3) 0.71062(8) 0.17222(13) 0.0422(4) Uani 1 1 d . . . . .
H25A H 0.975(4) 0.6881(12) 0.2288(19) 0.099(8) Uiso 1 1 d . . . . .
H25B H 1.150(4) 0.7165(11) 0.1735(17) 0.086(7) Uiso 1 1 d . . . . .
H25C H 0.962(4) 0.6828(12) 0.1192(19) 0.092(8) Uiso 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
O1 C3 1.3554(16) . ?
O1 C4 1.3855(16) . ?
O2 C11 1.2178(17) . ?
O3 C18 1.2285(16) . ?
C1 C2 1.5127(17) . ?
C1 C5 1.5144(18) . ?
C1 C10 1.5396(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.3343(18) . ?
C2 C18 1.4691(18) . ?
C3 H3 0.9500 . ?
C4 C9 1.3863(19) . ?
C4 C5 1.387(2) . ?
C5 C6 1.3930(19) . ?
C6 C7 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.5099(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.4993(19) . ?
C12 C13 1.384(2) . ?
C12 C17 1.386(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.4974(18) . ?
C19 C20 1.3937(19) . ?
C19 C24 1.3967(18) . ?
C20 C21 1.3843(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(2) . ?
C22 C25 1.506(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.96(3) . ?
C25 H25B 0.95(3) . ?
C25 H25C 0.98(3) . ?

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 117.93(10) . . ?
C2 C1 C5 110.54(11) . . ?
C2 C1 C10 112.56(10) . . ?
C5 C1 C10 111.86(11) . . ?
C2 C1 H1 107.2 . . ?
C5 C1 H1 107.2 . . ?
C10 C1 H1 107.2 . . ?
C3 C2 C18 120.32(12) . . ?
C3 C2 C1 121.75(12) . . ?
C18 C2 C1 117.78(11) . . ?
C2 C3 O1 125.51(12) . . ?
C2 C3 H3 117.2 . . ?
O1 C3 H3 117.2 . . ?
O1 C4 C9 115.27(12) . . ?
O1 C4 C5 122.26(12) . . ?
C9 C4 C5 122.46(13) . . ?
C4 C5 C6 116.84(13) . . ?
C4 C5 C1 121.63(12) . . ?
C6 C5 C1 121.53(13) . . ?
C7 C6 C5 121.60(15) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 120.02(15) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.87(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 119.21(15) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C11 C10 C1 115.48(11) . . ?
C11 C10 H10A 108.4 . . ?
C1 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C1 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
O2 C11 C12 120.04(13) . . ?
O2 C11 C10 121.80(12) . . ?
C12 C11 C10 118.16(12) . . ?
C13 C12 C17 118.44(14) . . ?
C13 C12 C11 118.35(13) . . ?
C17 C12 C11 123.22(13) . . ?
C12 C13 C14 120.51(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.51(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.55(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.43(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.54(16) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O3 C18 C2 119.70(12) . . ?
O3 C18 C19 119.17(12) . . ?
C2 C18 C19 121.09(11) . . ?
C20 C19 C24 118.45(12) . . ?
C20 C19 C18 122.46(11) . . ?
C24 C19 C18 118.99(12) . . ?
C21 C20 C19 120.42(12) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.43(13) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 117.82(13) . . ?
C21 C22 C25 120.77(13) . . ?
C23 C22 C25 121.40(13) . . ?
C24 C23 C22 121.36(13) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C19 120.49(12) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C22 C25 H25A 113.6(15) . . ?
C22 C25 H25B 112.4(14) . . ?
H25A C25 H25B 103(2) . . ?
C22 C25 H25C 113.0(14) . . ?
H25A C25 H25C 109(2) . . ?
H25B C25 H25C 105(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 4.66(17) . . . . ?
C10 C1 C2 C3 -121.23(14) . . . . ?
C5 C1 C2 C18 -170.96(11) . . . . ?
C10 C1 C2 C18 63.16(15) . . . . ?
C18 C2 C3 O1 175.54(12) . . . . ?
C1 C2 C3 O1 0.0(2) . . . . ?
C4 O1 C3 C2 -5.18(19) . . . . ?
C3 O1 C4 C9 -174.22(12) . . . . ?
C3 O1 C4 C5 5.02(18) . . . . ?
O1 C4 C5 C6 -179.44(12) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
O1 C4 C5 C1 0.07(19) . . . . ?
C9 C4 C5 C1 179.25(12) . . . . ?
C2 C1 C5 C4 -4.63(17) . . . . ?
C10 C1 C5 C4 121.65(13) . . . . ?
C2 C1 C5 C6 174.86(12) . . . . ?
C10 C1 C5 C6 -58.87(16) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C1 C5 C6 C7 -179.87(13) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
O1 C4 C9 C8 180.00(12) . . . . ?
C5 C4 C9 C8 0.8(2) . . . . ?
C2 C1 C10 C11 61.31(15) . . . . ?
C5 C1 C10 C11 -63.86(14) . . . . ?
C1 C10 C11 O2 -7.02(19) . . . . ?
C1 C10 C11 C12 173.18(11) . . . . ?
O2 C11 C12 C13 -7.9(2) . . . . ?
C10 C11 C12 C13 171.87(13) . . . . ?
O2 C11 C12 C17 172.09(14) . . . . ?
C10 C11 C12 C17 -8.11(19) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 179.75(14) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C12 -1.3(2) . . . . ?
C13 C12 C17 C16 1.4(2) . . . . ?
C11 C12 C17 C16 -178.66(14) . . . . ?
C3 C2 C18 O3 -155.85(13) . . . . ?
C1 C2 C18 O3 19.83(18) . . . . ?
C3 C2 C18 C19 26.35(19) . . . . ?
C1 C2 C18 C19 -157.97(11) . . . . ?
O3 C18 C19 C20 -144.96(13) . . . . ?
C2 C18 C19 C20 32.85(19) . . . . ?
O3 C18 C19 C24 31.36(19) . . . . ?
C2 C18 C19 C24 -150.84(12) . . . . ?
C24 C19 C20 C21 1.1(2) . . . . ?
C18 C19 C20 C21 177.41(12) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C20 C21 C22 C23 -1.6(2) . . . . ?
C20 C21 C22 C25 177.19(14) . . . . ?
C21 C22 C23 C24 0.8(2) . . . . ?
C25 C22 C23 C24 -178.05(14) . . . . ?
C22 C23 C24 C19 1.0(2) . . . . ?
C20 C19 C24 C23 -1.9(2) . . . . ?
C18 C19 C24 C23 -178.40(12) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate - petroleum ether'
