# 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_dbr-4
_database_code_depnum_ccdc_archive 'CCDC 1038959'
_audit_update_record             
;
2014-12-12 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_cell_setting           orthorhombic

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'

_cell_length_a                   9.1967(5)
_cell_length_b                   10.3931(7)
_cell_length_c                   19.4118(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1855.42(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3253
_cell_measurement_theta_min      4.2617
_cell_measurement_theta_max      72.7513

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7419
_exptl_absorpt_correction_T_max  0.7725
_exptl_absorpt_process_details   
;
CrysAlis, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8848
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.56
_diffrn_reflns_theta_max         72.81
_reflns_number_total             3641
_reflns_number_gt                3152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.1317P)²+0.1424P] 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       0.0066(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1803
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_chemical_absolute_configuration ad

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7431(2) 0.1665(2) 0.77150(12) 0.0364(5) Uani 1 1 d . . .
C2 C 0.7691(3) 0.0553(3) 0.73301(16) 0.0472(6) Uani 1 1 d . . .
H2 H 0.7068 -0.0148 0.7369 0.057 Uiso 1 1 calc R . .
C3 C 0.8876(3) 0.0494(3) 0.68893(16) 0.0503(6) Uani 1 1 d . . .
H3 H 0.9040 -0.0249 0.6634 0.060 Uiso 1 1 calc R . .
C4 C 0.9813(3) 0.1520(3) 0.68249(14) 0.0499(7) Uani 1 1 d . . .
H4 H 1.0608 0.1474 0.6530 0.060 Uiso 1 1 calc R . .
C5 C 0.9550(3) 0.2628(3) 0.72081(15) 0.0510(7) Uani 1 1 d . . .
H5 H 1.0173 0.3329 0.7168 0.061 Uiso 1 1 calc R . .
C6 C 0.8380(3) 0.2692(3) 0.76433(14) 0.0437(6) Uani 1 1 d . . .
H6 H 0.8220 0.3440 0.7896 0.052 Uiso 1 1 calc R . .
C7 C 0.6204(2) 0.1740(3) 0.82374(13) 0.0380(5) Uani 1 1 d . . .
H7 H 0.6040 0.2649 0.8347 0.046 Uiso 1 1 calc R . .
C8 C 0.6656(3) 0.1049(4) 0.89035(15) 0.0555(8) Uani 1 1 d . . .
H8A H 0.7068 0.0218 0.8786 0.067 Uiso 1 1 calc R . .
H8B H 0.7408 0.1548 0.9130 0.067 Uiso 1 1 calc R . .
C9 C 0.5428(3) 0.0852(3) 0.93945(14) 0.0521(7) Uani 1 1 d . . .
H9 H 0.5663 0.0634 0.9846 0.063 Uiso 1 1 calc R . .
C10 C 0.4022(3) 0.0962(2) 0.92406(12) 0.0359(5) Uani 1 1 d . . .
C11 C 0.2873(3) 0.0722(2) 0.97610(13) 0.0399(5) Uani 1 1 d . . .
C12 C 0.1474(3) 0.0627(3) 0.95705(13) 0.0416(6) Uani 1 1 d . . .
C13 C 0.0961(3) 0.0794(3) 0.88371(14) 0.0502(7) Uani 1 1 d . . .
H13A H 0.0555 0.1649 0.8782 0.060 Uiso 1 1 calc R . .
H13B H 0.0197 0.0176 0.8742 0.060 Uiso 1 1 calc R . .
C14 C 0.2181(3) 0.0610(3) 0.83245(13) 0.0451(6) Uani 1 1 d . . .
H14A H 0.1856 0.0878 0.7871 0.054 Uiso 1 1 calc R . .
H14B H 0.2433 -0.0295 0.8301 0.054 Uiso 1 1 calc R . .
C15 C 0.3525(2) 0.1386(2) 0.85267(11) 0.0317(5) Uani 1 1 d . . .
C16 C 0.4770(2) 0.1166(2) 0.80076(12) 0.0342(5) Uani 1 1 d . . .
H16 H 0.4904 0.0236 0.7954 0.041 Uiso 1 1 calc R . .
C17 C 0.3360(4) 0.0533(4) 1.04928(14) 0.0611(9) Uani 1 1 d . . .
H17A H 0.2538 0.0315 1.0774 0.092 Uiso 1 1 calc R . .
H17B H 0.3794 0.1313 1.0660 0.092 Uiso 1 1 calc R . .
H17C H 0.4061 -0.0151 1.0512 0.092 Uiso 1 1 calc R . .
C18 C 0.0314(3) 0.0366(3) 1.00855(15) 0.0503(7) Uani 1 1 d . . .
C19 C -0.1497(6) -0.1027(5) 1.0455(3) 0.1018(17) Uani 1 1 d . . .
H19A H -0.1090 -0.1040 1.0916 0.122 Uiso 1 1 calc R . .
H19B H -0.2271 -0.0393 1.0445 0.122 Uiso 1 1 calc R . .
C20 C -0.2022(13) -0.2160(8) 1.0305(7) 0.251(7) Uani 1 1 d . . .
H20A H -0.2134 -0.2234 0.9815 0.377 Uiso 1 1 calc R . .
H20B H -0.2951 -0.2265 1.0523 0.377 Uiso 1 1 calc R . .
H20C H -0.1368 -0.2813 1.0466 0.377 Uiso 1 1 calc R . .
H1 H 0.382(4) 0.307(4) 0.880(2) 0.070(11) Uiso 1 1 d . . .
N1 N 0.4328(2) 0.1710(3) 0.73165(11) 0.0462(5) Uani 1 1 d . . .
O1 O 0.3100(2) 0.27056(18) 0.85374(10) 0.0421(4) Uani 1 1 d . . .
O2 O 0.4592(3) 0.2830(2) 0.71952(12) 0.0689(7) Uani 1 1 d . . .
O3 O 0.3706(3) 0.0985(3) 0.69174(11) 0.0748(8) Uani 1 1 d . . .
O4 O 0.0070(4) 0.0997(3) 1.05892(19) 0.1108(13) Uani 1 1 d . . .
O5 O -0.0377(3) -0.0675(3) 0.99632(16) 0.0896(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(4) . ?
C1 C2 1.396(4) . ?
C1 C7 1.519(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C16 1.515(3) . ?
C7 C8 1.537(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.492(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.332(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.483(3) . ?
C10 C15 1.524(3) . ?
C11 C12 1.342(4) . ?
C11 C17 1.503(4) . ?
C12 C18 1.487(4) . ?
C12 C13 1.510(4) . ?
C13 C14 1.512(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.527(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.426(3) . ?
C15 C16 1.542(3) . ?
C16 N1 1.512(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O4 1.198(4) . ?
C18 O5 1.277(4) . ?
C19 C20 1.305(9) . ?
C19 O5 1.452(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 O2 1.212(4) . ?
N1 O3 1.223(3) . ?
O1 H1 0.91(4) . ?

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
C6 C1 C2 118.4(2) . . ?
C6 C1 C7 119.7(2) . . ?
C2 C1 C7 121.8(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C16 C7 C1 115.47(19) . . ?
C16 C7 C8 107.4(2) . . ?
C1 C7 C8 109.7(2) . . ?
C16 C7 H7 108.0 . . ?
C1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C9 C8 C7 113.4(2) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 125.4(2) . . ?
C10 C9 H9 117.3 . . ?
C8 C9 H9 117.3 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 C15 121.3(2) . . ?
C11 C10 C15 117.0(2) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 C17 122.5(3) . . ?
C10 C11 C17 117.0(2) . . ?
C11 C12 C18 121.1(2) . . ?
C11 C12 C13 123.4(2) . . ?
C18 C12 C13 115.5(2) . . ?
C12 C13 C14 111.9(2) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.4(2) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O1 C15 C10 110.33(19) . . ?
O1 C15 C14 106.83(19) . . ?
C10 C15 C14 108.9(2) . . ?
O1 C15 C16 110.86(19) . . ?
C10 C15 C16 109.17(17) . . ?
C14 C15 C16 110.74(18) . . ?
N1 C16 C7 110.4(2) . . ?
N1 C16 C15 108.95(18) . . ?
C7 C16 C15 113.29(18) . . ?
N1 C16 H16 108.0 . . ?
C7 C16 H16 108.0 . . ?
C15 C16 H16 108.0 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 121.5(3) . . ?
O4 C18 C12 125.7(3) . . ?
O5 C18 C12 112.7(2) . . ?
C20 C19 O5 110.1(5) . . ?
C20 C19 H19A 109.6 . . ?
O5 C19 H19A 109.6 . . ?
C20 C19 H19B 109.7 . . ?
O5 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 N1 O3 124.2(3) . . ?
O2 N1 C16 118.5(2) . . ?
O3 N1 C16 117.2(3) . . ?
C15 O1 H1 102(3) . . ?
C18 O5 C19 116.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        72.81
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_dbr30
_database_code_depnum_ccdc_archive 'CCDC 1038960'
_audit_update_record             
;
2014-12-12 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N O5'
_chemical_formula_weight         361.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_cell_setting           monoclinic

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

_cell_length_a                   8.9810(4)
_cell_length_b                   11.3115(5)
_cell_length_c                   9.4917(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.099(7)
_cell_angle_gamma                90.00
_cell_volume                     893.41(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4203
_cell_measurement_theta_min      3.9072
_cell_measurement_theta_max      72.8252
_chemical_absolute_configuration rm
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7338
_exptl_absorpt_correction_T_max  0.8218
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4718
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.32
_diffrn_reflns_theta_max         72.99
_reflns_number_total             2805
_reflns_number_gt                2769
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_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)+(0.0654P)²+0.1774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(18)
_refine_ls_number_reflns         2805
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5892(2) 0.38091(16) 0.57041(19) 0.0177(4) Uani 1 1 d . . .
C2 C 0.7286(2) 0.42495(17) 0.56968(18) 0.0168(3) Uani 1 1 d . . .
C3 C 0.8854(2) 0.37586(17) 0.67254(19) 0.0161(3) Uani 1 1 d . . .
C4 C 0.8791(2) 0.26222(16) 0.75632(19) 0.0164(3) Uani 1 1 d . . .
C5 C 0.7436(2) 0.27316(18) 0.8151(2) 0.0205(4) Uani 1 1 d . . .
H5A H 0.7405 0.2029 0.8726 0.025 Uiso 1 1 calc R . .
H5B H 0.7630 0.3408 0.8824 0.025 Uiso 1 1 calc R . .
C6 C 0.5842(2) 0.28796(19) 0.6836(2) 0.0201(4) Uani 1 1 d . . .
H6A H 0.5029 0.3097 0.7232 0.024 Uiso 1 1 calc R . .
H6B H 0.5531 0.2129 0.6315 0.024 Uiso 1 1 calc R . .
C7 C 0.4277(2) 0.41495(17) 0.45874(19) 0.0183(4) Uani 1 1 d . . .
C8 C 0.1512(2) 0.3636(2) 0.3683(2) 0.0294(5) Uani 1 1 d . . .
H8A H 0.1174 0.4385 0.3934 0.044 Uiso 1 1 calc R . .
H8B H 0.0828 0.3023 0.3801 0.044 Uiso 1 1 calc R . .
H8C H 0.1444 0.3650 0.2649 0.044 Uiso 1 1 calc R . .
C9 C 1.0261(2) 0.42579(16) 0.68845(18) 0.0173(3) Uani 1 1 d . . .
H01 H 1.0225 0.4950 0.6345 0.021 Uiso 1 1 calc R . .
C10 C 1.1892(2) 0.37941(17) 0.78616(19) 0.0178(3) Uani 1 1 d . . .
H10 H 1.2554 0.3802 0.7243 0.021 Uiso 1 1 calc R . .
C11 C 1.1815(2) 0.25056(15) 0.83532(19) 0.0160(3) Uani 1 1 d . . .
H11 H 1.1538 0.2000 0.7452 0.019 Uiso 1 1 calc R . .
C12 C 1.0420(2) 0.24732(16) 0.89035(19) 0.0167(3) Uani 1 1 d . . .
H12 H 1.0551 0.3136 0.9606 0.020 Uiso 1 1 calc R . .
C13 C 0.7378(2) 0.52339(18) 0.4651(2) 0.0229(4) Uani 1 1 d . . .
H13A H 0.6342 0.5342 0.3856 0.034 Uiso 1 1 calc R . .
H13B H 0.8148 0.5030 0.4213 0.034 Uiso 1 1 calc R . .
H13C H 0.7702 0.5953 0.5221 0.034 Uiso 1 1 calc R . .
C14 C 1.2696(2) 0.46278(17) 0.9221(2) 0.0197(4) Uani 1 1 d . . .
H14A H 1.2831 0.5402 0.8846 0.024 Uiso 1 1 calc R . .
H14B H 1.1999 0.4715 0.9786 0.024 Uiso 1 1 calc R . .
C15 C 1.4336(2) 0.41643(17) 1.0287(2) 0.0194(4) Uani 1 1 d . . .
H15A H 1.5061 0.4124 0.9746 0.023 Uiso 1 1 calc R . .
H15B H 1.4794 0.4702 1.1138 0.023 Uiso 1 1 calc R . .
C16 C 1.4153(2) 0.29366(16) 1.08731(19) 0.0172(4) Uani 1 1 d . . .
H16 H 1.3372 0.3005 1.1364 0.021 Uiso 1 1 calc R . .
C17 C 1.3434(2) 0.20922(17) 0.9521(2) 0.0179(3) Uani 1 1 d . . .
H17A H 1.4189 0.2006 0.9018 0.021 Uiso 1 1 calc R . .
H17B H 1.3295 0.1320 0.9900 0.021 Uiso 1 1 calc R . .
C18 C 1.5677(2) 0.24221(17) 1.2037(2) 0.0197(4) Uani 1 1 d . . .
C19 C 1.7143(2) 0.2820(2) 1.2264(2) 0.0264(4) Uani 1 1 d . . .
H19A H 1.8037 0.2462 1.2986 0.032 Uiso 1 1 calc R . .
H19B H 1.7273 0.3457 1.1702 0.032 Uiso 1 1 calc R . .
C20 C 1.5436(2) 0.1396(2) 1.2931(2) 0.0257(4) Uani 1 1 d . . .
H20A H 1.4969 0.0748 1.2257 0.039 Uiso 1 1 calc R . .
H20B H 1.4732 0.1626 1.3434 0.039 Uiso 1 1 calc R . .
H20C H 1.6454 0.1158 1.3676 0.039 Uiso 1 1 calc R . .
N1 N 1.04400(18) 0.13434(16) 0.97521(16) 0.0212(3) Uani 1 1 d . . .
O O 0.85120(15) 0.16834(11) 0.64994(14) 0.0197(3) Uani 1 1 d . . .
H0 H 0.8016 0.1153 0.6720 0.030 Uiso 1 1 calc R . .
O3 O 1.0453(2) 0.14365(16) 1.10377(17) 0.0383(4) Uani 1 1 d . . .
O4 O 1.04529(19) 0.03980(12) 0.91429(17) 0.0311(3) Uani 1 1 d . . .
O5 O 0.39256(15) 0.49568(13) 0.36838(15) 0.0233(3) Uani 1 1 d . . .
O6 O 0.31529(16) 0.34075(14) 0.46861(15) 0.0266(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.350(3) . ?
C1 C7 1.489(2) . ?
C1 C6 1.516(3) . ?
C2 C3 1.487(2) . ?
C2 C13 1.514(3) . ?
C3 C9 1.339(3) . ?
C3 C4 1.524(2) . ?
C4 O 1.421(2) . ?
C4 C5 1.523(2) . ?
C4 C12 1.545(2) . ?
C5 C6 1.513(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O5 1.211(2) . ?
C7 O6 1.343(2) . ?
C8 O6 1.445(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.504(2) . ?
C9 H01 0.9300 . ?
C10 C11 1.540(2) . ?
C10 C14 1.541(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.528(2) . ?
C11 C17 1.533(2) . ?
C11 H11 0.9800 . ?
C12 N1 1.507(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.532(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.528(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.515(2) . ?
C16 C17 1.534(2) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.330(3) . ?
C18 C20 1.501(3) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 O4 1.218(2) . ?
N1 O3 1.221(2) . ?
O H0 0.8200 . ?

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 C7 123.90(16) . . ?
C2 C1 C6 122.29(16) . . ?
C7 C1 C6 113.78(15) . . ?
C1 C2 C3 120.68(16) . . ?
C1 C2 C13 123.64(16) . . ?
C3 C2 C13 115.67(15) . . ?
C9 C3 C2 122.47(16) . . ?
C9 C3 C4 121.04(16) . . ?
C2 C3 C4 116.47(15) . . ?
O C4 C5 111.67(14) . . ?
O C4 C3 106.91(13) . . ?
C5 C4 C3 108.32(14) . . ?
O C4 C12 111.28(14) . . ?
C5 C4 C12 110.30(14) . . ?
C3 C4 C12 108.19(14) . . ?
C6 C5 C4 110.22(14) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 112.96(15) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O5 C7 O6 121.24(16) . . ?
O5 C7 C1 128.58(16) . . ?
O6 C7 C1 110.18(15) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C10 125.56(16) . . ?
C3 C9 H01 117.2 . . ?
C10 C9 H01 117.2 . . ?
C9 C10 C11 111.86(14) . . ?
C9 C10 C14 110.10(15) . . ?
C11 C10 C14 112.70(14) . . ?
C9 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
C14 C10 H10 107.3 . . ?
C12 C11 C17 114.98(14) . . ?
C12 C11 C10 105.23(13) . . ?
C17 C11 C10 111.65(14) . . ?
C12 C11 H11 108.3 . . ?
C17 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
N1 C12 C11 110.89(14) . . ?
N1 C12 C4 110.47(14) . . ?
C11 C12 C4 111.09(13) . . ?
N1 C12 H12 108.1 . . ?
C11 C12 H12 108.1 . . ?
C4 C12 H12 108.1 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 112.00(15) . . ?
C15 C14 H14A 109.2 . . ?
C10 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C10 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 110.06(14) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C18 C16 C15 115.03(14) . . ?
C18 C16 C17 110.56(14) . . ?
C15 C16 C17 109.30(14) . . ?
C18 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C17 C16 H16 107.2 . . ?
C11 C17 C16 113.65(14) . . ?
C11 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C11 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C20 120.95(17) . . ?
C19 C18 C16 123.78(18) . . ?
C20 C18 C16 115.26(16) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 N1 O3 123.52(17) . . ?
O4 N1 C12 119.42(14) . . ?
O3 N1 C12 117.06(17) . . ?
C4 O H0 109.5 . . ?
C7 O6 C8 116.71(15) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        72.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
