# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_160928e
_database_code_depnum_ccdc_archive 'CCDC 1834022'
_audit_update_record             
;
2018-04-01 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35

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   C2/c

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

_cell_length_a                   17.0463(15)
_cell_length_b                   11.4307(11)
_cell_length_c                   18.4621(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.898(2)
_cell_angle_gamma                90.00
_cell_volume                     3423.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1209
_cell_measurement_theta_min      2.281
_cell_measurement_theta_max      20.172

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8441
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1735
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3023
_reflns_number_gt                1382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)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         3023
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.2243
_refine_ls_wR_factor_gt          0.1741
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
O1 O 0.4283(2) 0.5612(4) 0.6407(2) 0.1148(14) Uani 1 1 d . . .
O2 O 0.30692(18) 0.6459(3) 0.60590(18) 0.0918(11) Uani 1 1 d . . .
O3 O 0.34608(15) 0.9046(3) 0.37976(14) 0.0674(9) Uani 1 1 d . . .
H3 H 0.3011 0.9040 0.3873 0.101 Uiso 1 1 calc R . .
O4 O 0.61864(16) 0.8155(2) 0.70005(15) 0.0645(8) Uani 1 1 d . . .
C1 C 0.3795(3) 0.6548(4) 0.6287(2) 0.0642(12) Uani 1 1 d . . .
C2 C 0.4266(2) 0.7644(4) 0.6422(2) 0.0662(12) Uani 1 1 d . . .
H2A H 0.4757 0.7545 0.6854 0.079 Uiso 1 1 calc R . .
H2B H 0.3935 0.8257 0.6546 0.079 Uiso 1 1 calc R . .
C3 C 0.4514(2) 0.8016(3) 0.57372(19) 0.0484(10) Uani 1 1 d . . .
C4 C 0.3888(2) 0.8380(3) 0.5086(2) 0.0500(10) Uani 1 1 d . . .
H4 H 0.3346 0.8406 0.5098 0.060 Uiso 1 1 calc R . .
C5 C 0.4054(2) 0.8696(3) 0.4439(2) 0.0483(10) Uani 1 1 d . . .
C6 C 0.4870(2) 0.8683(3) 0.4408(2) 0.0466(9) Uani 1 1 d . . .
C7 C 0.5069(2) 0.9040(4) 0.3752(2) 0.0570(11) Uani 1 1 d . . .
H7 H 0.4651 0.9280 0.3323 0.068 Uiso 1 1 calc R . .
C8 C 0.5862(3) 0.9036(4) 0.3742(2) 0.0677(12) Uani 1 1 d . . .
H8 H 0.5981 0.9257 0.3302 0.081 Uiso 1 1 calc R . .
C9 C 0.6498(3) 0.8703(4) 0.4385(3) 0.0631(12) Uani 1 1 d . . .
H9 H 0.7040 0.8715 0.4375 0.076 Uiso 1 1 calc R . .
C10 C 0.6332(2) 0.8357(3) 0.5032(2) 0.0520(10) Uani 1 1 d . . .
H10 H 0.6764 0.8139 0.5457 0.062 Uiso 1 1 calc R . .
C11 C 0.5515(2) 0.8325(3) 0.5065(2) 0.0428(9) Uani 1 1 d . . .
C12 C 0.5314(2) 0.7974(3) 0.57298(19) 0.0418(9) Uani 1 1 d . . .
C13 C 0.5991(2) 0.7572(3) 0.6418(2) 0.0451(9) Uani 1 1 d . . .
C14 C 0.6394(2) 0.6424(3) 0.6390(2) 0.0463(9) Uani 1 1 d . . .
C15 C 0.7110(2) 0.6132(4) 0.6962(2) 0.0557(11) Uani 1 1 d . . .
H15 H 0.7352 0.6670 0.7343 0.067 Uiso 1 1 calc R . .
C16 C 0.7461(2) 0.5047(4) 0.6967(3) 0.0661(12) Uani 1 1 d . . .
H16 H 0.7944 0.4857 0.7349 0.079 Uiso 1 1 calc R . .
C17 C 0.7104(3) 0.4250(4) 0.6414(3) 0.0713(13) Uani 1 1 d . . .
H17 H 0.7340 0.3514 0.6426 0.086 Uiso 1 1 calc R . .
C18 C 0.6401(3) 0.4524(4) 0.5844(3) 0.0753(13) Uani 1 1 d . . .
H18 H 0.6164 0.3977 0.5467 0.090 Uiso 1 1 calc R . .
C19 C 0.6038(2) 0.5616(4) 0.5825(2) 0.0593(11) Uani 1 1 d . . .
H19 H 0.5559 0.5803 0.5437 0.071 Uiso 1 1 calc R . .
C20 C 0.3944(5) 0.4419(6) 0.6244(4) 0.135(2) Uani 1 1 d . . .
H20A H 0.3466 0.4430 0.5793 0.162 Uiso 1 1 calc R . .
H20B H 0.4354 0.3908 0.6145 0.162 Uiso 1 1 calc R . .
C21 C 0.3714(5) 0.3979(7) 0.6877(5) 0.171(3) Uani 1 1 d . . .
H21A H 0.4199 0.3870 0.7305 0.257 Uiso 1 1 calc R . .
H21B H 0.3435 0.3244 0.6742 0.257 Uiso 1 1 calc R . .
H21C H 0.3353 0.4528 0.7008 0.257 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
O1 C1 1.332(5) . ?
O1 C20 1.475(7) . ?
O2 C1 1.182(4) . ?
O3 C5 1.360(4) . ?
O3 H3 0.8200 . ?
O4 C13 1.221(4) . ?
C1 C2 1.468(6) . ?
C2 C3 1.511(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C12 1.369(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.359(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(5) . ?
C6 C7 1.413(5) . ?
C6 C11 1.424(5) . ?
C7 C8 1.357(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.412(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.430(4) . ?
C12 C13 1.502(5) . ?
C13 C14 1.490(5) . ?
C14 C19 1.385(5) . ?
C14 C15 1.387(5) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.433(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C1 O1 C20 121.6(5) . . ?
C5 O3 H3 109.5 . . ?
O2 C1 O1 121.5(5) . . ?
O2 C1 C2 126.3(4) . . ?
O1 C1 C2 112.1(4) . . ?
C1 C2 C3 112.2(3) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C12 C3 C4 120.0(3) . . ?
C12 C3 C2 122.3(3) . . ?
C4 C3 C2 117.7(3) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 O3 122.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
O3 C5 C6 116.5(3) . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 C11 118.8(3) . . ?
C7 C6 C11 119.1(3) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 118.0(3) . . ?
C10 C11 C12 123.0(3) . . ?
C6 C11 C12 119.1(3) . . ?
C3 C12 C11 120.1(3) . . ?
C3 C12 C13 120.7(3) . . ?
C11 C12 C13 119.2(3) . . ?
O4 C13 C14 120.5(3) . . ?
O4 C13 C12 120.6(3) . . ?
C14 C13 C12 118.8(3) . . ?
C19 C14 C15 119.5(4) . . ?
C19 C14 C13 120.9(3) . . ?
C15 C14 C13 119.5(4) . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.5(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.4(4) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 O1 110.2(6) . . ?
C21 C20 H20A 109.6 . . ?
O1 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
O1 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C20 O1 C1 O2 1.6(7) . . . . ?
C20 O1 C1 C2 -174.8(4) . . . . ?
O2 C1 C2 C3 -92.7(5) . . . . ?
O1 C1 C2 C3 83.4(4) . . . . ?
C1 C2 C3 C12 -109.5(4) . . . . ?
C1 C2 C3 C4 68.6(5) . . . . ?
C12 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C5 -178.1(4) . . . . ?
C3 C4 C5 O3 179.6(3) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
O3 C5 C6 C7 1.4(5) . . . . ?
C4 C5 C6 C11 0.5(5) . . . . ?
O3 C5 C6 C11 179.9(3) . . . . ?
C5 C6 C7 C8 178.9(4) . . . . ?
C11 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C6 -1.1(5) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C5 C6 C11 C10 -177.8(3) . . . . ?
C7 C6 C11 C10 0.8(5) . . . . ?
C5 C6 C11 C12 0.9(5) . . . . ?
C7 C6 C11 C12 179.4(3) . . . . ?
C4 C3 C12 C11 1.3(5) . . . . ?
C2 C3 C12 C11 179.3(3) . . . . ?
C4 C3 C12 C13 -179.2(3) . . . . ?
C2 C3 C12 C13 -1.2(5) . . . . ?
C10 C11 C12 C3 176.8(3) . . . . ?
C6 C11 C12 C3 -1.8(5) . . . . ?
C10 C11 C12 C13 -2.6(5) . . . . ?
C6 C11 C12 C13 178.8(3) . . . . ?
C3 C12 C13 O4 -67.4(5) . . . . ?
C11 C12 C13 O4 112.1(4) . . . . ?
C3 C12 C13 C14 109.9(4) . . . . ?
C11 C12 C13 C14 -70.6(4) . . . . ?
O4 C13 C14 C19 162.1(4) . . . . ?
C12 C13 C14 C19 -15.2(5) . . . . ?
O4 C13 C14 C15 -14.0(5) . . . . ?
C12 C13 C14 C15 168.8(3) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 176.2(3) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 1.0(6) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C15 C14 C19 C18 0.3(6) . . . . ?
C13 C14 C19 C18 -175.7(3) . . . . ?
C17 C18 C19 C14 0.0(6) . . . . ?
C1 O1 C20 C21 -84.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_161217d
_database_code_depnum_ccdc_archive 'CCDC 1834023'
_audit_update_record             
;
2018-04-01 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 N O3'
_chemical_formula_weight         409.46

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   14.9117(12)
_cell_length_b                   9.0532(8)
_cell_length_c                   16.0374(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.025(2)
_cell_angle_gamma                90.00
_cell_volume                     2138.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1012
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      18.895

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10547
_diffrn_reflns_av_R_equivalents  0.1569
_diffrn_reflns_av_sigmaI/netI    0.1554
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3761
_reflns_number_gt                1589
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1980P)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     SHELXL
_refine_ls_extinction_coef       0.001(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2188
_refine_ls_R_factor_gt           0.1367
_refine_ls_wR_factor_ref         0.4177
_refine_ls_wR_factor_gt          0.3854
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
N1 N 0.1069(4) 1.0456(7) 0.1256(4) 0.0544(17) Uani 1 1 d . . .
O1 O 0.3288(4) 0.6975(6) 0.0387(4) 0.0767(18) Uani 1 1 d . . .
O2 O 0.3936(4) 0.8417(6) -0.0434(4) 0.0752(18) Uani 1 1 d . . .
O3 O 0.5358(3) 1.1941(7) 0.1910(3) 0.0714(18) Uani 1 1 d . . .
H3 H 0.5590 1.1732 0.1495 0.107 Uiso 1 1 calc R . .
C1 C 0.3384(5) 0.8203(9) 0.0030(5) 0.0507(19) Uani 1 1 d . . .
C2 C 0.2780(5) 0.9391(8) 0.0262(4) 0.0509(19) Uani 1 1 d . . .
H2A H 0.2207 0.8961 0.0350 0.061 Uiso 1 1 calc R . .
H2B H 0.2657 1.0088 -0.0201 0.061 Uiso 1 1 calc R . .
C3 C 0.3198(4) 1.0206(7) 0.1054(4) 0.0398(17) Uani 1 1 d . . .
C4 C 0.4099(4) 1.0691(7) 0.1144(4) 0.0442(18) Uani 1 1 d . . .
H4 H 0.4436 1.0484 0.0716 0.053 Uiso 1 1 calc R . .
C5 C 0.4483(4) 1.1420(8) 0.1803(4) 0.0467(18) Uani 1 1 d . . .
C6 C 0.4010(5) 1.1752(8) 0.2493(4) 0.0463(18) Uani 1 1 d . . .
C7 C 0.4397(6) 1.2577(9) 0.3186(5) 0.063(2) Uani 1 1 d . . .
H7 H 0.4985 1.2936 0.3211 0.076 Uiso 1 1 calc R . .
C8 C 0.3930(6) 1.2866(10) 0.3824(5) 0.069(2) Uani 1 1 d . . .
H8 H 0.4191 1.3435 0.4281 0.082 Uiso 1 1 calc R . .
C9 C 0.3046(5) 1.2302(9) 0.3793(5) 0.062(2) Uani 1 1 d . . .
H9 H 0.2725 1.2470 0.4237 0.075 Uiso 1 1 calc R . .
C10 C 0.2669(5) 1.1516(8) 0.3116(5) 0.055(2) Uani 1 1 d . . .
H10 H 0.2080 1.1162 0.3098 0.066 Uiso 1 1 calc R . .
C11 C 0.3125(4) 1.1210(7) 0.2439(4) 0.0413(17) Uani 1 1 d . . .
C12 C 0.2722(4) 1.0453(8) 0.1707(4) 0.0443(18) Uani 1 1 d . . .
C13 C 0.1778(5) 0.9872(8) 0.1675(4) 0.0491(19) Uani 1 1 d . . .
C14 C 0.1675(5) 0.8513(9) 0.2176(5) 0.054(2) Uani 1 1 d . . .
C15 C 0.2381(5) 0.7521(9) 0.2371(5) 0.064(2) Uani 1 1 d . . .
H15 H 0.2940 0.7717 0.2205 0.077 Uiso 1 1 calc R . .
C16 C 0.2265(6) 0.6275(10) 0.2798(6) 0.076(3) Uani 1 1 d . . .
H16 H 0.2742 0.5606 0.2914 0.091 Uiso 1 1 calc R . .
C17 C 0.1454(8) 0.5977(12) 0.3063(6) 0.087(3) Uani 1 1 d . . .
H17 H 0.1371 0.5098 0.3341 0.104 Uiso 1 1 calc R . .
C18 C 0.0785(8) 0.6967(14) 0.2918(6) 0.096(3) Uani 1 1 d . . .
H18 H 0.0249 0.6800 0.3130 0.115 Uiso 1 1 calc R . .
C19 C 0.0870(5) 0.8216(11) 0.2465(6) 0.079(3) Uani 1 1 d . . .
H19 H 0.0385 0.8869 0.2350 0.095 Uiso 1 1 calc R . .
C20 C 0.1115(4) 1.1758(9) 0.0784(5) 0.051(2) Uani 1 1 d . . .
C21 C 0.1394(6) 1.3070(10) 0.1144(6) 0.072(3) Uani 1 1 d . . .
H21 H 0.1617 1.3098 0.1719 0.087 Uiso 1 1 calc R . .
C22 C 0.1359(6) 1.4346(11) 0.0692(7) 0.082(3) Uani 1 1 d . . .
H22 H 0.1552 1.5232 0.0953 0.098 Uiso 1 1 calc R . .
C23 C 0.1036(7) 1.4304(12) -0.0153(8) 0.092(3) Uani 1 1 d . . .
H23 H 0.0998 1.5165 -0.0473 0.111 Uiso 1 1 calc R . .
C24 C 0.0769(6) 1.2993(13) -0.0520(6) 0.084(3) Uani 1 1 d . . .
H24 H 0.0581 1.2949 -0.1101 0.101 Uiso 1 1 calc R . .
C25 C 0.0773(5) 1.1745(10) -0.0051(6) 0.066(2) Uani 1 1 d . . .
H25 H 0.0539 1.0874 -0.0304 0.079 Uiso 1 1 calc R . .
C26 C 0.3863(8) 0.5766(11) 0.0205(8) 0.111(4) Uani 1 1 d . . .
H26A H 0.3611 0.5304 -0.0326 0.133 Uiso 1 1 calc R . .
H26B H 0.4465 0.6131 0.0158 0.133 Uiso 1 1 calc R . .
C27 C 0.3917(8) 0.4717(13) 0.0873(9) 0.123(4) Uani 1 1 d . . .
H27A H 0.4117 0.5202 0.1402 0.184 Uiso 1 1 calc R . .
H27B H 0.4340 0.3954 0.0789 0.184 Uiso 1 1 calc R . .
H27C H 0.3329 0.4290 0.0880 0.184 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
N1 C13 1.275(9) . ?
N1 C20 1.408(9) . ?
O1 C1 1.270(9) . ?
O1 C26 1.449(11) . ?
O2 C1 1.208(9) . ?
O3 C5 1.372(8) . ?
O3 H3 0.8200 . ?
C1 C2 1.487(10) . ?
C2 C3 1.517(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C12 1.371(9) . ?
C3 C4 1.400(9) . ?
C4 C5 1.301(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.434(10) . ?
C6 C7 1.387(10) . ?
C6 C11 1.399(9) . ?
C7 C8 1.351(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.346(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.410(9) . ?
C12 C13 1.496(9) . ?
C13 C14 1.490(10) . ?
C14 C19 1.380(11) . ?
C14 C15 1.381(10) . ?
C15 C16 1.345(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.334(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(13) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.357(10) . ?
C20 C21 1.357(11) . ?
C21 C22 1.361(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.357(14) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(13) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.425(14) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C13 N1 C20 121.6(6) . . ?
C1 O1 C26 117.2(7) . . ?
C5 O3 H3 109.5 . . ?
O2 C1 O1 123.7(8) . . ?
O2 C1 C2 122.4(7) . . ?
O1 C1 C2 113.9(7) . . ?
C1 C2 C3 112.1(6) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C12 C3 C4 118.3(6) . . ?
C12 C3 C2 121.7(6) . . ?
C4 C3 C2 120.0(6) . . ?
C5 C4 C3 122.4(6) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 O3 124.4(6) . . ?
C4 C5 C6 121.8(6) . . ?
O3 C5 C6 113.8(6) . . ?
C7 C6 C11 120.6(7) . . ?
C7 C6 C5 122.5(7) . . ?
C11 C6 C5 116.9(6) . . ?
C8 C7 C6 120.8(8) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.7(7) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.4(7) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 122.7(7) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C6 116.9(6) . . ?
C10 C11 C12 123.3(6) . . ?
C6 C11 C12 119.8(6) . . ?
C3 C12 C11 120.8(6) . . ?
C3 C12 C13 120.9(6) . . ?
C11 C12 C13 118.3(6) . . ?
N1 C13 C14 118.7(6) . . ?
N1 C13 C12 124.7(7) . . ?
C14 C13 C12 116.6(6) . . ?
C19 C14 C15 118.0(8) . . ?
C19 C14 C13 120.7(7) . . ?
C15 C14 C13 121.3(7) . . ?
C16 C15 C14 120.4(8) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.9(9) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.0(10) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.5(9) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C14 120.0(9) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C25 C20 C21 118.0(8) . . ?
C25 C20 N1 118.7(7) . . ?
C21 C20 N1 122.8(7) . . ?
C20 C21 C22 122.2(9) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C23 118.9(10) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 119.3(9) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.8(10) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C20 120.6(9) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C27 C26 O1 108.4(9) . . ?
C27 C26 H26A 110.0 . . ?
O1 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
O1 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C26 O1 C1 O2 -1.5(13) . . . . ?
C26 O1 C1 C2 -179.0(8) . . . . ?
O2 C1 C2 C3 -90.5(9) . . . . ?
O1 C1 C2 C3 87.1(8) . . . . ?
C1 C2 C3 C12 -131.0(7) . . . . ?
C1 C2 C3 C4 47.2(9) . . . . ?
C12 C3 C4 C5 -3.2(10) . . . . ?
C2 C3 C4 C5 178.6(7) . . . . ?
C3 C4 C5 O3 -178.7(7) . . . . ?
C3 C4 C5 C6 1.2(11) . . . . ?
C4 C5 C6 C7 -177.4(7) . . . . ?
O3 C5 C6 C7 2.5(11) . . . . ?
C4 C5 C6 C11 2.1(11) . . . . ?
O3 C5 C6 C11 -177.9(6) . . . . ?
C11 C6 C7 C8 0.5(12) . . . . ?
C5 C6 C7 C8 -180.0(8) . . . . ?
C6 C7 C8 C9 1.1(13) . . . . ?
C7 C8 C9 C10 -1.9(13) . . . . ?
C8 C9 C10 C11 1.1(12) . . . . ?
C9 C10 C11 C6 0.5(11) . . . . ?
C9 C10 C11 C12 -176.7(7) . . . . ?
C7 C6 C11 C10 -1.3(11) . . . . ?
C5 C6 C11 C10 179.1(6) . . . . ?
C7 C6 C11 C12 176.0(7) . . . . ?
C5 C6 C11 C12 -3.5(10) . . . . ?
C4 C3 C12 C11 1.7(10) . . . . ?
C2 C3 C12 C11 179.8(6) . . . . ?
C4 C3 C12 C13 -175.8(6) . . . . ?
C2 C3 C12 C13 2.4(10) . . . . ?
C10 C11 C12 C3 178.8(7) . . . . ?
C6 C11 C12 C3 1.7(10) . . . . ?
C10 C11 C12 C13 -3.6(10) . . . . ?
C6 C11 C12 C13 179.2(7) . . . . ?
C20 N1 C13 C14 178.6(6) . . . . ?
C20 N1 C13 C12 -1.3(11) . . . . ?
C3 C12 C13 N1 -78.4(10) . . . . ?
C11 C12 C13 N1 104.1(8) . . . . ?
C3 C12 C13 C14 101.8(8) . . . . ?
C11 C12 C13 C14 -75.8(8) . . . . ?
N1 C13 C14 C19 -25.6(11) . . . . ?
C12 C13 C14 C19 154.2(8) . . . . ?
N1 C13 C14 C15 154.9(7) . . . . ?
C12 C13 C14 C15 -25.3(10) . . . . ?
C19 C14 C15 C16 2.9(12) . . . . ?
C13 C14 C15 C16 -177.6(7) . . . . ?
C14 C15 C16 C17 -1.4(13) . . . . ?
C15 C16 C17 C18 -2.2(15) . . . . ?
C16 C17 C18 C19 4.3(16) . . . . ?
C17 C18 C19 C14 -2.8(16) . . . . ?
C15 C14 C19 C18 -0.8(13) . . . . ?
C13 C14 C19 C18 179.7(8) . . . . ?
C13 N1 C20 C25 123.9(8) . . . . ?
C13 N1 C20 C21 -63.6(10) . . . . ?
C25 C20 C21 C22 -1.5(13) . . . . ?
N1 C20 C21 C22 -174.0(8) . . . . ?
C20 C21 C22 C23 -0.2(15) . . . . ?
C21 C22 C23 C24 -0.8(15) . . . . ?
C22 C23 C24 C25 3.7(15) . . . . ?
C23 C24 C25 C20 -5.5(14) . . . . ?
C21 C20 C25 C24 4.3(12) . . . . ?
N1 C20 C25 C24 177.2(7) . . . . ?
C1 O1 C26 C27 157.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.082
