# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1027197'
_audit_update_record             
;
2014-10-01 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4c
_chemical_name_common            
3-(4-Chlorophenyl)-2-(2-hydroxybenzoyl)-4H-furo[3,2-c]chromen-4-one
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H13 Cl O5'
_chemical_formula_weight         416.79

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/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                   11.644(3)
_cell_length_b                   14.685(2)
_cell_length_c                   11.1346(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.878(12)
_cell_angle_gamma                90.00
_cell_volume                     1902.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14881
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_sigmaI/netI    0.0850
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3715
_reflns_number_gt                2035
_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)+(0.1170P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
Cl1 Cl 0.72251(11) -0.16818(6) 1.15886(9) 0.0734(4) Uani 1 1 d . . .
O3 O 0.7961(2) 0.35350(15) 0.91856(18) 0.0492(6) Uani 1 1 d . . .
O1 O 0.5855(2) 0.39835(16) 1.1951(2) 0.0574(7) Uani 1 1 d . . .
O4 O 0.8625(3) 0.13546(18) 0.8122(2) 0.0665(8) Uani 1 1 d . . .
O2 O 0.5922(3) 0.25161(18) 1.2406(2) 0.0705(8) Uani 1 1 d . . .
C15 C 0.7319(4) -0.0537(2) 1.1201(3) 0.0514(9) Uani 1 1 d . . .
C18 C 0.8847(3) 0.2160(2) 0.8382(3) 0.0483(9) Uani 1 1 d . . .
C1 C 0.6836(3) 0.4658(2) 1.0265(3) 0.0463(8) Uani 1 1 d . . .
O5 O 0.9907(3) 0.14527(19) 0.6313(2) 0.0695(8) Uani 1 1 d . . .
H5 H 0.9481 0.1204 0.6785 0.104 Uiso 1 1 calc R . .
C19 C 0.9766(3) 0.2653(2) 0.7790(3) 0.0475(9) Uani 1 1 d . . .
C9 C 0.7234(3) 0.3759(2) 1.0053(3) 0.0445(8) Uani 1 1 d . . .
C12 C 0.7451(3) 0.1273(2) 1.0555(3) 0.0449(8) Uani 1 1 d . . .
C10 C 0.8135(3) 0.2600(2) 0.9274(3) 0.0469(9) Uani 1 1 d . . .
C14 C 0.6324(3) -0.0049(2) 1.0994(3) 0.0573(10) Uani 1 1 d . . .
H14 H 0.5611 -0.0326 1.1070 0.069 Uiso 1 1 calc R . .
C11 C 0.7512(3) 0.2238(2) 1.0190(3) 0.0456(8) Uani 1 1 d . . .
C8 C 0.6945(3) 0.3006(2) 1.0704(3) 0.0454(8) Uani 1 1 d . . .
C4 C 0.5843(3) 0.6309(3) 1.0850(3) 0.0584(10) Uani 1 1 d . . .
H4 H 0.5507 0.6864 1.1038 0.070 Uiso 1 1 calc R . .
C24 C 1.0233(3) 0.3473(3) 0.8234(3) 0.0536(9) Uani 1 1 d . . .
H24 H 0.9951 0.3724 0.8933 0.064 Uiso 1 1 calc R . .
C5 C 0.5630(3) 0.5555(3) 1.1540(3) 0.0597(10) Uani 1 1 d . . .
H5A H 0.5161 0.5598 1.2197 0.072 Uiso 1 1 calc R . .
C20 C 1.0241(3) 0.2269(3) 0.6758(3) 0.0529(10) Uani 1 1 d . . .
C2 C 0.7051(3) 0.5438(2) 0.9582(3) 0.0524(9) Uani 1 1 d . . .
H2 H 0.7530 0.5405 0.8931 0.063 Uiso 1 1 calc R . .
C17 C 0.8435(3) 0.0771(2) 1.0786(3) 0.0516(9) Uani 1 1 d . . .
H17 H 0.9150 0.1045 1.0715 0.062 Uiso 1 1 calc R . .
C6 C 0.6123(3) 0.4728(2) 1.1245(3) 0.0519(9) Uani 1 1 d . . .
C7 C 0.6224(3) 0.3102(2) 1.1723(3) 0.0516(9) Uani 1 1 d . . .
C21 C 1.1072(3) 0.2744(3) 0.6145(3) 0.0645(11) Uani 1 1 d . . .
H21 H 1.1335 0.2520 0.5422 0.077 Uiso 1 1 calc R . .
C16 C 0.8373(3) -0.0136(2) 1.1123(3) 0.0543(9) Uani 1 1 d . . .
H16 H 0.9040 -0.0467 1.1293 0.065 Uiso 1 1 calc R . .
C13 C 0.6397(3) 0.0855(3) 1.0671(3) 0.0561(10) Uani 1 1 d . . .
H13 H 0.5727 0.1188 1.0529 0.067 Uiso 1 1 calc R . .
C3 C 0.6553(3) 0.6251(2) 0.9878(3) 0.0581(10) Uani 1 1 d . . .
H3 H 0.6692 0.6767 0.9422 0.070 Uiso 1 1 calc R . .
C23 C 1.1097(3) 0.3911(3) 0.7655(3) 0.0628(11) Uani 1 1 d . . .
H23 H 1.1407 0.4450 0.7964 0.075 Uiso 1 1 calc R . .
C22 C 1.1502(4) 0.3542(3) 0.6607(4) 0.0694(12) Uani 1 1 d . . .
H22 H 1.2079 0.3843 0.6208 0.083 Uiso 1 1 calc R . .


_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
Cl1 C15 1.740(4) . ?
O3 C9 1.346(4) . ?
O3 C10 1.390(4) . ?
O1 C6 1.387(4) . ?
O1 C7 1.390(4) . ?
O4 C18 1.243(4) . ?
O2 C7 1.207(4) . ?
C15 C16 1.367(5) . ?
C15 C14 1.376(5) . ?
C18 C10 1.465(5) . ?
C18 C19 1.467(5) . ?
C1 C6 1.396(5) . ?
C1 C2 1.403(5) . ?
C1 C9 1.421(5) . ?
O5 C20 1.349(4) . ?
C19 C24 1.404(5) . ?
C19 C20 1.410(5) . ?
C9 C8 1.369(4) . ?
C12 C17 1.379(5) . ?
C12 C13 1.383(5) . ?
C12 C11 1.477(5) . ?
C10 C11 1.377(4) . ?
C14 C13 1.379(5) . ?
C11 C8 1.435(5) . ?
C8 C7 1.441(5) . ?
C4 C5 1.375(5) . ?
C4 C3 1.386(5) . ?
C24 C23 1.373(5) . ?
C5 C6 1.387(5) . ?
C20 C21 1.391(5) . ?
C2 C3 1.372(5) . ?
C17 C16 1.387(5) . ?
C21 C22 1.368(6) . ?
C23 C22 1.384(6) . ?

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
C9 O3 C10 106.5(2) . . ?
C6 O1 C7 123.6(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 Cl1 119.7(3) . . ?
C14 C15 Cl1 119.0(3) . . ?
O4 C18 C10 117.4(3) . . ?
O4 C18 C19 121.0(3) . . ?
C10 C18 C19 121.6(3) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 C9 113.8(3) . . ?
C2 C1 C9 127.1(3) . . ?
C24 C19 C20 118.2(3) . . ?
C24 C19 C18 123.0(3) . . ?
C20 C19 C18 118.7(3) . . ?
O3 C9 C8 110.7(3) . . ?
O3 C9 C1 124.3(3) . . ?
C8 C9 C1 125.0(3) . . ?
C17 C12 C13 118.7(3) . . ?
C17 C12 C11 121.1(3) . . ?
C13 C12 C11 120.2(3) . . ?
C11 C10 O3 110.8(3) . . ?
C11 C10 C18 130.9(3) . . ?
O3 C10 C18 118.1(3) . . ?
C15 C14 C13 119.1(4) . . ?
C10 C11 C8 104.6(3) . . ?
C10 C11 C12 127.3(3) . . ?
C8 C11 C12 128.1(3) . . ?
C9 C8 C11 107.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C11 C8 C7 132.7(3) . . ?
C5 C4 C3 120.6(3) . . ?
C23 C24 C19 121.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
O5 C20 C21 117.5(3) . . ?
O5 C20 C19 122.6(3) . . ?
C21 C20 C19 119.8(4) . . ?
C3 C2 C1 119.7(3) . . ?
C12 C17 C16 120.9(3) . . ?
C5 C6 O1 117.0(3) . . ?
C5 C6 C1 120.7(3) . . ?
O1 C6 C1 122.4(3) . . ?
O2 C7 O1 116.8(3) . . ?
O2 C7 C8 128.0(3) . . ?
O1 C7 C8 115.2(3) . . ?
C22 C21 C20 119.8(4) . . ?
C15 C16 C17 119.1(3) . . ?
C14 C13 C12 121.0(4) . . ?
C2 C3 C4 120.6(3) . . ?
C24 C23 C22 119.2(4) . . ?
C21 C22 C23 121.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.081
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1027198'
_audit_update_record             
;
2014-10-01 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        5c
_chemical_name_common            
'4-(2-(2-Hydroxy-5-methylbenzoyl)-8-methyl-4-oxo-4H-furo[3,2-c]chromen-3-yl)benzonitrile '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 N O5'
_chemical_formula_weight         435.42

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'
N N 0.0061 0.0033 '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   'Pbca '

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                   17.409(3)
_cell_length_b                   11.222(2)
_cell_length_c                   21.848(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4268.2(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50267
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4191
_reflns_number_gt                3012
_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)+(0.0651P)²+1.8032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4191
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.80511(7) 0.96260(12) 0.88896(6) 0.0490(3) Uani 1 1 d . . .
O1 O 0.79486(8) 1.26719(14) 0.78837(7) 0.0624(4) Uani 1 1 d . . .
C20 C 0.92288(10) 1.03953(18) 0.86638(9) 0.0461(5) Uani 1 1 d . . .
C7 C 0.86354(11) 1.11310(18) 0.83985(9) 0.0459(5) Uani 1 1 d . . .
C9 C 0.72170(11) 1.10469(19) 0.83475(9) 0.0505(5) Uani 1 1 d . . .
C21 C 1.00706(10) 1.05545(18) 0.86043(9) 0.0466(5) Uani 1 1 d . . .
C14 C 0.78706(12) 0.7689(2) 0.97235(10) 0.0538(5) Uani 1 1 d . . .
H14 H 0.7616 0.8350 0.9566 0.065 Uiso 1 1 calc R . .
O5 O 0.98173(9) 0.64828(16) 0.98820(9) 0.0785(5) Uani 1 1 d . . .
H5 H 1.0011 0.7047 0.9700 0.118 Uiso 1 1 calc R . .
O2 O 0.92199(9) 1.27416(15) 0.78647(9) 0.0754(5) Uani 1 1 d . . .
C11 C 0.88434(10) 0.95061(18) 0.89642(9) 0.0488(5) Uani 1 1 d . . .
O4 O 0.98522(8) 0.84838(18) 0.93833(10) 0.0872(6) Uani 1 1 d . . .
C8 C 0.79513(11) 1.06170(19) 0.85428(9) 0.0478(5) Uani 1 1 d . . .
C22 C 1.04284(12) 1.1569(2) 0.88160(10) 0.0588(6) Uani 1 1 d . . .
H22 H 1.0139 1.2163 0.9002 0.071 Uiso 1 1 calc R . .
C13 C 0.86693(11) 0.76175(18) 0.96514(9) 0.0494(5) Uani 1 1 d . . .
C6 C 0.86635(12) 1.21987(19) 0.80384(10) 0.0543(5) Uani 1 1 d . . .
C5 C 0.72600(12) 1.2106(2) 0.80090(10) 0.0548(5) Uani 1 1 d . . .
C12 C 0.91423(11) 0.85262(19) 0.93393(10) 0.0546(5) Uani 1 1 d . . .
C19 C 0.90488(13) 0.66151(19) 0.98955(10) 0.0580(5) Uani 1 1 d . . .
C27 C 1.05139(12) 0.9688(2) 0.83187(11) 0.0580(6) Uani 1 1 d . . .
H27 H 1.0279 0.9003 0.8170 0.070 Uiso 1 1 calc R . .
C4 C 0.65947(13) 1.2622(2) 0.77818(11) 0.0659(6) Uani 1 1 d . . .
H4 H 0.6616 1.3330 0.7561 0.079 Uiso 1 1 calc R . .
C10 C 0.65045(11) 1.0520(2) 0.84536(10) 0.0580(6) Uani 1 1 d . . .
H10 H 0.6478 0.9820 0.8681 0.070 Uiso 1 1 calc R . .
C2 C 0.58382(12) 1.1016(3) 0.82284(11) 0.0661(7) Uani 1 1 d . . .
C24 C 1.16460(12) 1.0838(2) 0.84738(10) 0.0624(6) Uani 1 1 d . . .
C26 C 1.12982(12) 0.9828(2) 0.82524(11) 0.0650(6) Uani 1 1 d . . .
H26 H 1.1588 0.9242 0.8059 0.078 Uiso 1 1 calc R . .
C15 C 0.74433(13) 0.6820(2) 1.00188(10) 0.0617(6) Uani 1 1 d . . .
C18 C 0.86181(16) 0.5720(2) 1.01746(12) 0.0702(7) Uani 1 1 d . . .
H18 H 0.8864 0.5044 1.0324 0.084 Uiso 1 1 calc R . .
C3 C 0.59024(14) 1.2068(3) 0.78896(11) 0.0706(7) Uani 1 1 d . . .
H3 H 0.5458 1.2407 0.7730 0.085 Uiso 1 1 calc R . .
C17 C 0.78400(16) 0.5823(2) 1.02310(11) 0.0711(7) Uani 1 1 d . . .
H17 H 0.7566 0.5210 1.0417 0.085 Uiso 1 1 calc R . .
C23 C 1.12115(13) 1.1713(2) 0.87550(10) 0.0670(7) Uani 1 1 d . . .
H23 H 1.1447 1.2399 0.8903 0.080 Uiso 1 1 calc R . .
C16 C 0.65922(14) 0.6951(3) 1.01120(13) 0.0841(8) Uani 1 1 d . . .
H16A H 0.6496 0.7321 1.0501 0.126 Uiso 1 1 calc R . .
H16B H 0.6355 0.6179 1.0103 0.126 Uiso 1 1 calc R . .
H16C H 0.6382 0.7436 0.9791 0.126 Uiso 1 1 calc R . .
C25 C 1.24660(14) 1.0995(3) 0.84004(12) 0.0903(10) Uani 1 1 d . . .
C1 C 0.50671(13) 1.0439(3) 0.83324(14) 0.0922(9) Uani 1 1 d . . .
H1A H 0.5080 0.9990 0.8706 0.138 Uiso 1 1 calc R . .
H1B H 0.4952 0.9917 0.7997 0.138 Uiso 1 1 calc R . .
H1C H 0.4679 1.1044 0.8361 0.138 Uiso 1 1 calc R . .
N1 N 1.31115(13) 1.1107(4) 0.83437(15) 0.1443(15) 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
O3 C8 1.357(2) . ?
O3 C11 1.395(2) . ?
O1 C5 1.384(3) . ?
O1 C6 1.395(2) . ?
C20 C11 1.370(3) . ?
C20 C7 1.444(3) . ?
C20 C21 1.482(2) . ?
C7 C8 1.360(3) . ?
C7 C6 1.434(3) . ?
C9 C10 1.394(3) . ?
C9 C5 1.402(3) . ?
C9 C8 1.431(3) . ?
C21 C22 1.377(3) . ?
C21 C27 1.390(3) . ?
C14 C15 1.386(3) . ?
C14 C13 1.402(3) . ?
O5 C19 1.346(3) . ?
O2 C6 1.206(2) . ?
C11 C12 1.467(3) . ?
O4 C12 1.240(2) . ?
C22 C23 1.379(3) . ?
C13 C19 1.409(3) . ?
C13 C12 1.477(3) . ?
C5 C4 1.387(3) . ?
C19 C18 1.394(3) . ?
C27 C26 1.382(3) . ?
C4 C3 1.377(4) . ?
C10 C2 1.378(3) . ?
C2 C3 1.397(4) . ?
C2 C1 1.507(3) . ?
C24 C26 1.373(4) . ?
C24 C23 1.384(4) . ?
C24 C25 1.447(3) . ?
C15 C17 1.394(4) . ?
C15 C16 1.503(3) . ?
C18 C17 1.365(3) . ?
C25 N1 1.138(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
C8 O3 C11 105.71(14) . . ?
C5 O1 C6 123.40(17) . . ?
C11 C20 C7 104.98(16) . . ?
C11 C20 C21 127.89(18) . . ?
C7 C20 C21 127.11(18) . . ?
C8 C7 C6 120.74(18) . . ?
C8 C7 C20 106.91(18) . . ?
C6 C7 C20 132.34(18) . . ?
C10 C9 C5 119.68(19) . . ?
C10 C9 C8 127.0(2) . . ?
C5 C9 C8 113.28(18) . . ?
C22 C21 C27 118.55(19) . . ?
C22 C21 C20 121.16(18) . . ?
C27 C21 C20 120.28(18) . . ?
C15 C14 C13 123.0(2) . . ?
C20 C11 O3 110.98(17) . . ?
C20 C11 C12 129.79(18) . . ?
O3 C11 C12 119.22(17) . . ?
O3 C8 C7 111.40(16) . . ?
O3 C8 C9 123.85(18) . . ?
C7 C8 C9 124.7(2) . . ?
C21 C22 C23 120.8(2) . . ?
C14 C13 C19 117.92(19) . . ?
C14 C13 C12 124.43(19) . . ?
C19 C13 C12 117.65(18) . . ?
O2 C6 O1 116.6(2) . . ?
O2 C6 C7 128.5(2) . . ?
O1 C6 C7 114.87(18) . . ?
O1 C5 C4 117.5(2) . . ?
O1 C5 C9 122.65(18) . . ?
C4 C5 C9 119.9(2) . . ?
O4 C12 C11 115.18(19) . . ?
O4 C12 C13 119.55(19) . . ?
C11 C12 C13 125.28(17) . . ?
O5 C19 C18 117.7(2) . . ?
O5 C19 C13 123.1(2) . . ?
C18 C19 C13 119.2(2) . . ?
C26 C27 C21 121.1(2) . . ?
C3 C4 C5 118.8(2) . . ?
C2 C10 C9 121.2(2) . . ?
C10 C2 C3 117.6(2) . . ?
C10 C2 C1 121.5(3) . . ?
C3 C2 C1 120.9(2) . . ?
C26 C24 C23 120.1(2) . . ?
C26 C24 C25 119.7(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C26 C27 119.5(2) . . ?
C14 C15 C17 117.0(2) . . ?
C14 C15 C16 121.6(2) . . ?
C17 C15 C16 121.5(2) . . ?
C17 C18 C19 120.8(2) . . ?
C4 C3 C2 122.9(2) . . ?
C18 C17 C15 122.0(2) . . ?
C22 C23 C24 120.0(2) . . ?
N1 C25 C24 179.4(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
