# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 N O8'
_chemical_formula_weight         395.40

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   P2(1)2(1)2(1)

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                   9.7254(9)
_cell_length_b                   9.9683(9)
_cell_length_c                   20.3950(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1977.2(3)
_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            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_T_max  0.9616
_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_reflns_number            23185
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3489
_reflns_number_gt                3022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0469P)²+0.2980P] 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   0.6(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.6993(2) -0.10992(19) 1.02847(9) 0.0819(6) Uani 1 1 d . . .
O2 O 0.56510(16) -0.28309(17) 1.05419(7) 0.0665(4) Uani 1 1 d . . .
O3 O 0.96247(19) -0.22928(18) 0.72282(10) 0.0824(5) Uani 1 1 d . . .
O4 O 0.96527(16) -0.01396(17) 0.69194(7) 0.0654(4) Uani 1 1 d . . .
O5 O 0.37202(16) 0.02109(15) 0.99388(7) 0.0608(4) Uani 1 1 d . . .
O6 O 0.49856(15) 0.16449(13) 0.93165(7) 0.0508(4) Uani 1 1 d . . .
O7 O 0.39085(18) -0.0324(2) 0.75959(9) 0.0880(6) Uani 1 1 d . . .
O8 O 0.55784(15) -0.18230(16) 0.76686(7) 0.0582(4) Uani 1 1 d . . .
N1 N 0.52766(17) -0.05562(15) 0.92071(8) 0.0450(4) Uani 1 1 d . . .
C1 C 0.5313(2) -0.18824(19) 0.95087(9) 0.0457(5) Uani 1 1 d . . .
H1A H 0.4378 -0.2225 0.9573 0.055 Uiso 1 1 calc R . .
C2 C 0.6078(2) -0.2727(2) 0.90021(10) 0.0540(5) Uani 1 1 d . . .
H2A H 0.5436 -0.3148 0.8702 0.065 Uiso 1 1 calc R . .
H2B H 0.6615 -0.3421 0.9216 0.065 Uiso 1 1 calc R . .
C3 C 0.7020(2) -0.17455(19) 0.86343(9) 0.0455(5) Uani 1 1 d . . .
H3A H 0.7961 -0.1816 0.8803 0.055 Uiso 1 1 calc R . .
C4 C 0.7017(2) -0.1950(2) 0.78896(10) 0.0486(5) Uani 1 1 d . . .
H4A H 0.7388 -0.2834 0.7776 0.058 Uiso 1 1 calc R . .
C5 C 0.7841(2) -0.0862(2) 0.75767(9) 0.0480(5) Uani 1 1 d . . .
C6 C 0.7336(2) 0.0347(2) 0.76901(10) 0.0522(5) Uani 1 1 d . . .
H6A H 0.7736 0.1129 0.7531 0.063 Uiso 1 1 calc R . .
C7 C 0.6050(2) 0.0335(2) 0.81016(9) 0.0502(5) Uani 1 1 d . . .
H7A H 0.5669 0.1238 0.8160 0.060 Uiso 1 1 calc R . .
C8 C 0.64487(19) -0.03222(18) 0.87671(9) 0.0409(4) Uani 1 1 d . . .
H8A H 0.7145 0.0224 0.8989 0.049 Uiso 1 1 calc R . .
C9 C 0.5058(2) -0.0582(3) 0.77719(10) 0.0580(6) Uani 1 1 d . . .
C10 C 0.4584(2) 0.0438(2) 0.95233(9) 0.0459(5) Uani 1 1 d . . .
C11 C 0.4182(2) 0.2867(2) 0.94592(10) 0.0498(5) Uani 1 1 d . . .
C12 C 0.2816(3) 0.2754(3) 0.91263(17) 0.0878(9) Uani 1 1 d . . .
H12A H 0.2282 0.2065 0.9334 0.132 Uiso 1 1 calc R . .
H12B H 0.2950 0.2530 0.8673 0.132 Uiso 1 1 calc R . .
H12C H 0.2338 0.3594 0.9158 0.132 Uiso 1 1 calc R . .
C13 C 0.5042(3) 0.3948(2) 0.91494(17) 0.0914(10) Uani 1 1 d . . .
H13A H 0.5905 0.4015 0.9376 0.137 Uiso 1 1 calc R . .
H13B H 0.4566 0.4790 0.9177 0.137 Uiso 1 1 calc R . .
H13C H 0.5205 0.3731 0.8698 0.137 Uiso 1 1 calc R . .
C14 C 0.4036(3) 0.3101(3) 1.01831(13) 0.0813(8) Uani 1 1 d . . .
H14A H 0.4931 0.3172 1.0378 0.122 Uiso 1 1 calc R . .
H14B H 0.3548 0.2364 1.0377 0.122 Uiso 1 1 calc R . .
H14C H 0.3534 0.3917 1.0257 0.122 Uiso 1 1 calc R . .
C15 C 0.6085(2) -0.1857(2) 1.01524(10) 0.0496(5) Uani 1 1 d . . .
C16 C 0.6377(3) -0.3029(3) 1.11627(12) 0.0763(8) Uani 1 1 d . . .
H16A H 0.6049 -0.2395 1.1488 0.092 Uiso 1 1 calc R . .
H16B H 0.7356 -0.2890 1.1103 0.092 Uiso 1 1 calc R . .
C17 C 0.6109(3) -0.4408(3) 1.13792(13) 0.0819(8) Uani 1 1 d . . .
H17A H 0.6589 -0.4575 1.1782 0.123 Uiso 1 1 calc R . .
H17B H 0.6422 -0.5025 1.1050 0.123 Uiso 1 1 calc R . .
H17C H 0.5140 -0.4527 1.1447 0.123 Uiso 1 1 calc R . .
C18 C 0.9125(2) -0.1195(2) 0.72263(10) 0.0543(5) Uani 1 1 d . . .
C19 C 1.0939(3) -0.0348(3) 0.65833(13) 0.0848(8) Uani 1 1 d . . .
H19A H 1.1219 0.0473 0.6376 0.127 Uiso 1 1 calc R . .
H19B H 1.0826 -0.1033 0.6257 0.127 Uiso 1 1 calc R . .
H19C H 1.1627 -0.0621 0.6893 0.127 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 C15 1.194(3) . ?
O2 C15 1.323(2) . ?
O2 C16 1.463(3) . ?
O3 C18 1.198(3) . ?
O4 C18 1.327(3) . ?
O4 C19 1.441(3) . ?
O5 C10 1.215(2) . ?
O6 C10 1.333(2) . ?
O6 C11 1.476(2) . ?
O7 C9 1.202(3) . ?
O8 C9 1.353(3) . ?
O8 C4 1.475(3) . ?
N1 C10 1.361(3) . ?
N1 C1 1.459(3) . ?
N1 C8 1.469(2) . ?
C1 C15 1.512(3) . ?
C1 C2 1.526(3) . ?
C2 C3 1.536(3) . ?
C3 C4 1.533(3) . ?
C3 C8 1.547(3) . ?
C4 C5 1.492(3) . ?
C5 C6 1.321(3) . ?
C5 C18 1.477(3) . ?
C6 C7 1.506(3) . ?
C7 C9 1.490(3) . ?
C7 C8 1.557(3) . ?
C11 C12 1.496(3) . ?
C11 C14 1.501(3) . ?
C11 C13 1.504(3) . ?
C16 C17 1.468(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
C15 O2 C16 117.68(18) . . ?
C18 O4 C19 116.5(2) . . ?
C10 O6 C11 121.81(15) . . ?
C9 O8 C4 112.69(16) . . ?
C10 N1 C1 118.20(16) . . ?
C10 N1 C8 123.89(16) . . ?
C1 N1 C8 112.50(15) . . ?
N1 C1 C15 111.29(16) . . ?
N1 C1 C2 103.07(16) . . ?
C15 C1 C2 110.78(17) . . ?
C1 C2 C3 105.66(16) . . ?
C4 C3 C2 113.45(17) . . ?
C4 C3 C8 107.15(15) . . ?
C2 C3 C8 106.52(16) . . ?
O8 C4 C5 108.41(17) . . ?
O8 C4 C3 107.05(16) . . ?
C5 C4 C3 109.02(16) . . ?
C6 C5 C18 127.16(19) . . ?
C6 C5 C4 112.87(18) . . ?
C18 C5 C4 119.84(18) . . ?
C5 C6 C7 113.54(18) . . ?
C9 C7 C6 106.89(16) . . ?
C9 C7 C8 107.25(17) . . ?
C6 C7 C8 106.38(16) . . ?
N1 C8 C3 103.88(14) . . ?
N1 C8 C7 113.95(16) . . ?
C3 C8 C7 108.84(15) . . ?
O7 C9 O8 119.8(2) . . ?
O7 C9 C7 127.3(2) . . ?
O8 C9 C7 112.93(18) . . ?
O5 C10 O6 126.28(19) . . ?
O5 C10 N1 122.46(19) . . ?
O6 C10 N1 111.26(16) . . ?
O6 C11 C12 108.59(18) . . ?
O6 C11 C14 111.86(18) . . ?
C12 C11 C14 111.9(2) . . ?
O6 C11 C13 102.37(17) . . ?
C12 C11 C13 110.9(2) . . ?
C14 C11 C13 110.7(2) . . ?
O1 C15 O2 124.4(2) . . ?
O1 C15 C1 125.04(19) . . ?
O2 C15 C1 110.54(17) . . ?
O2 C16 C17 107.5(2) . . ?
O3 C18 O4 124.7(2) . . ?
O3 C18 C5 123.2(2) . . ?
O4 C18 C5 112.16(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 995983'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 N O8'
_chemical_formula_weight         395.40

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.0916(7)
_cell_length_b                   9.9171(13)
_cell_length_c                   10.6705(15)
_cell_angle_alpha                81.115(4)
_cell_angle_beta                 77.646(5)
_cell_angle_gamma                87.407(4)
_cell_volume                     519.96(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             210
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_T_max  0.9776
_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_reflns_number            5954
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2860
_reflns_number_gt                2393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1506P)²+0.1570P] 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   2(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     253
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.2046
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1059(11) 0.7805(5) 0.6166(5) 0.1034(17) Uani 1 1 d . . .
O2 O 0.4429(10) 0.7138(4) 0.4764(4) 0.0851(13) Uani 1 1 d . . .
O3 O 0.8319(11) 0.6814(4) 1.1295(4) 0.0924(14) Uani 1 1 d . . .
O4 O 0.8541(10) 0.4803(5) 1.2540(4) 0.0847(12) Uani 1 1 d . . .
O5 O 0.1634(12) 0.1056(4) 1.0325(5) 0.1060(17) Uani 1 1 d . . .
O6 O 0.3998(15) 0.0786(5) 1.1845(7) 0.126(2) Uani 1 1 d . . .
O7 O 0.5560(8) 0.2590(4) 0.6358(6) 0.1031(19) Uani 1 1 d . . .
O8 O 0.8357(7) 0.4168(3) 0.6623(4) 0.0676(10) Uani 1 1 d . . .
N1 N 0.4024(7) 0.4669(3) 0.6513(4) 0.0515(9) Uani 1 1 d . . .
H1A H 0.2650 0.4390 0.6281 0.062 Uiso 1 1 calc R . .
C1 C 0.6080(10) 0.4915(5) 1.0899(5) 0.0581(12) Uani 1 1 d . . .
C2 C 0.5517(11) 0.3555(5) 1.1223(5) 0.0657(13) Uani 1 1 d . . .
H2A H 0.6247 0.3018 1.1862 0.079 Uiso 1 1 calc R . .
C3 C 0.3838(11) 0.2987(5) 1.0582(5) 0.0630(13) Uani 1 1 d . . .
C4 C 0.2764(10) 0.3753(5) 0.9627(5) 0.0576(12) Uani 1 1 d . . .
H4A H 0.1663 0.3347 0.9205 0.069 Uiso 1 1 calc R . .
C5 C 0.3320(10) 0.5148(4) 0.9286(5) 0.0543(11) Uani 1 1 d . . .
C6 C 0.4976(10) 0.5710(4) 0.9935(5) 0.0562(12) Uani 1 1 d . . .
H6A H 0.5362 0.6635 0.9726 0.067 Uiso 1 1 calc R . .
C7 C 0.3918(8) 0.6002(4) 0.6904(4) 0.0463(10) Uani 1 1 d . . .
H7A H 0.5749 0.6237 0.6935 0.056 Uiso 1 1 calc R . .
C8 C 0.2168(10) 0.6015(4) 0.8253(5) 0.0573(12) Uani 1 1 d . . .
H8A H 0.1972 0.6946 0.8437 0.069 Uiso 1 1 calc R . .
H8B H 0.0393 0.5688 0.8269 0.069 Uiso 1 1 calc R . .
C9 C 0.2936(10) 0.7081(4) 0.5915(5) 0.0536(11) Uani 1 1 d . . .
C10 C 0.377(2) 0.8201(7) 0.3788(6) 0.099(2) Uani 1 1 d . . .
H10A H 0.4989 0.8149 0.2974 0.149 Uiso 1 1 calc R . .
H10B H 0.3920 0.9076 0.4044 0.149 Uiso 1 1 calc R . .
H10C H 0.1962 0.8085 0.3695 0.149 Uiso 1 1 calc R . .
C11 C 0.7738(12) 0.5616(5) 1.1580(5) 0.0661(14) Uani 1 1 d . . .
C12 C 1.0092(17) 0.5429(10) 1.3276(8) 0.103(2) Uani 1 1 d . . .
H12A H 1.0575 0.4753 1.3938 0.154 Uiso 1 1 calc R . .
H12B H 0.9039 0.6139 1.3672 0.154 Uiso 1 1 calc R . .
H12C H 1.1694 0.5812 1.2708 0.154 Uiso 1 1 calc R . .
C13 C 0.3194(14) 0.1513(6) 1.1005(6) 0.0773(16) Uani 1 1 d . . .
C14 C 0.092(2) -0.0386(7) 1.0665(11) 0.136(4) Uani 1 1 d . . .
H14A H -0.0190 -0.0609 1.0105 0.203 Uiso 1 1 calc R . .
H14B H -0.0049 -0.0555 1.1550 0.203 Uiso 1 1 calc R . .
H14C H 0.2526 -0.0939 1.0564 0.203 Uiso 1 1 calc R . .
C15 C 0.6209(9) 0.3846(4) 0.6498(5) 0.0547(11) Uani 1 1 d . . .
C16 C 0.7557(14) 0.1467(7) 0.6299(11) 0.110(3) Uani 1 1 d U . .
C17 C 0.590(2) 0.0269(11) 0.6183(12) 0.133(3) Uani 1 1 d U . .
H17A H 0.5246 0.0456 0.5392 0.199 Uiso 1 1 calc R . .
H17B H 0.4400 0.0139 0.6908 0.199 Uiso 1 1 calc R . .
H17C H 0.6998 -0.0543 0.6175 0.199 Uiso 1 1 calc R . .
C18 C 0.975(2) 0.1786(9) 0.5110(11) 0.136(4) Uani 1 1 d . . .
H18A H 1.0828 0.2510 0.5219 0.204 Uiso 1 1 calc R . .
H18B H 0.8958 0.2065 0.4368 0.204 Uiso 1 1 calc R . .
H18C H 1.0849 0.0988 0.4982 0.204 Uiso 1 1 calc R . .
C19 C 0.8609(18) 0.1205(8) 0.7516(12) 0.120(3) Uani 1 1 d . . .
H19A H 0.9617 0.1977 0.7579 0.180 Uiso 1 1 calc R . .
H19B H 0.9754 0.0409 0.7504 0.180 Uiso 1 1 calc R . .
H19C H 0.7132 0.1059 0.8249 0.180 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 C9 1.178(6) . ?
O2 C9 1.293(6) . ?
O2 C10 1.446(7) . ?
O3 C11 1.214(7) . ?
O4 C11 1.327(7) . ?
O4 C12 1.445(8) . ?
O5 C13 1.320(8) . ?
O5 C14 1.463(7) . ?
O6 C13 1.193(8) . ?
O7 C15 1.341(5) . ?
O7 C16 1.473(6) . ?
O8 C15 1.193(5) . ?
N1 C15 1.349(5) . ?
N1 C7 1.441(5) . ?
N1 H1A 0.8600 . ?
C1 C2 1.368(7) . ?
C1 C6 1.397(7) . ?
C1 C11 1.482(8) . ?
C2 C3 1.389(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(7) . ?
C3 C13 1.491(7) . ?
C4 C5 1.401(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(7) . ?
C5 C8 1.495(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.524(7) . ?
C7 C9 1.529(6) . ?
C7 H7A 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C19 1.491(15) . ?
C16 C18 1.501(15) . ?
C16 C17 1.524(12) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C9 O2 C10 116.3(5) . . ?
C11 O4 C12 116.4(6) . . ?
C13 O5 C14 116.5(6) . . ?
C15 O7 C16 121.4(4) . . ?
C15 N1 C7 122.1(4) . . ?
C15 N1 H1A 118.9 . . ?
C7 N1 H1A 118.9 . . ?
C2 C1 C6 120.0(5) . . ?
C2 C1 C11 122.4(5) . . ?
C6 C1 C11 117.5(4) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 C13 121.4(5) . . ?
C2 C3 C13 117.0(5) . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 118.0(5) . . ?
C6 C5 C8 120.5(4) . . ?
C4 C5 C8 121.5(5) . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 H6A 119.3 . . ?
C1 C6 H6A 119.3 . . ?
N1 C7 C8 111.7(4) . . ?
N1 C7 C9 111.0(4) . . ?
C8 C7 C9 110.6(4) . . ?
N1 C7 H7A 107.8 . . ?
C8 C7 H7A 107.8 . . ?
C9 C7 H7A 107.8 . . ?
C5 C8 C7 112.4(4) . . ?
C5 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 O2 123.1(5) . . ?
O1 C9 C7 124.3(5) . . ?
O2 C9 C7 112.6(4) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O4 122.8(5) . . ?
O3 C11 C1 123.9(6) . . ?
O4 C11 C1 113.3(4) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 O5 121.8(5) . . ?
O6 C13 C3 125.5(6) . . ?
O5 C13 C3 112.7(5) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 C15 O7 125.2(4) . . ?
O8 C15 N1 125.8(4) . . ?
O7 C15 N1 109.0(4) . . ?
O7 C16 C19 110.5(7) . . ?
O7 C16 C18 109.6(8) . . ?
C19 C16 C18 112.6(7) . . ?
O7 C16 C17 102.3(6) . . ?
C19 C16 C17 110.8(9) . . ?
C18 C16 C17 110.6(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 C1 C2 C3 -0.1(7) . . . . ?
C11 C1 C2 C3 176.8(5) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C1 C2 C3 C13 -177.6(5) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C13 C3 C4 C5 177.4(5) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 C8 -179.7(4) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C8 C5 C6 C1 -179.7(4) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
C11 C1 C6 C5 -177.5(4) . . . . ?
C15 N1 C7 C8 -105.1(5) . . . . ?
C15 N1 C7 C9 130.9(5) . . . . ?
C6 C5 C8 C7 92.6(5) . . . . ?
C4 C5 C8 C7 -87.4(5) . . . . ?
N1 C7 C8 C5 65.6(5) . . . . ?
C9 C7 C8 C5 -170.2(4) . . . . ?
C10 O2 C9 O1 3.2(9) . . . . ?
C10 O2 C9 C7 -175.4(5) . . . . ?
N1 C7 C9 O1 123.5(6) . . . . ?
C8 C7 C9 O1 -1.1(7) . . . . ?
N1 C7 C9 O2 -57.8(5) . . . . ?
C8 C7 C9 O2 177.6(4) . . . . ?
C12 O4 C11 O3 2.1(8) . . . . ?
C12 O4 C11 C1 -178.0(5) . . . . ?
C2 C1 C11 O3 178.3(6) . . . . ?
C6 C1 C11 O3 -4.7(8) . . . . ?
C2 C1 C11 O4 -1.6(7) . . . . ?
C6 C1 C11 O4 175.4(4) . . . . ?
C14 O5 C13 O6 0.7(12) . . . . ?
C14 O5 C13 C3 179.4(7) . . . . ?
C4 C3 C13 O6 -178.3(7) . . . . ?
C2 C3 C13 O6 0.0(10) . . . . ?
C4 C3 C13 O5 3.0(8) . . . . ?
C2 C3 C13 O5 -178.7(6) . . . . ?
C16 O7 C15 O8 -2.2(11) . . . . ?
C16 O7 C15 N1 179.5(7) . . . . ?
C7 N1 C15 O8 -10.8(8) . . . . ?
C7 N1 C15 O7 167.5(5) . . . . ?
C15 O7 C16 C19 60.4(10) . . . . ?
C15 O7 C16 C18 -64.3(9) . . . . ?
C15 O7 C16 C17 178.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 995986'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 N O5'
_chemical_formula_weight         359.41

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'
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)

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

_cell_length_a                   9.1672(5)
_cell_length_b                   7.7813(5)
_cell_length_c                   12.9980(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.487(2)
_cell_angle_gamma                90.00
_cell_volume                     914.50(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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_reflns_number            10650
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3023
_reflns_number_gt                2955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0358P)²+0.1377P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(7)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.23595(12) -0.34397(16) -0.12089(8) 0.0239(2) Uani 1 1 d . . .
O1 O 0.20953(11) 0.25048(14) 0.19822(7) 0.0321(2) Uani 1 1 d . . .
O2 O 0.31039(12) 0.05505(14) 0.31606(7) 0.0362(3) Uani 1 1 d . . .
O3 O 0.43446(11) -0.17413(16) -0.24392(8) 0.0395(3) Uani 1 1 d . . .
O4 O 0.23824(11) -0.15682(14) -0.37230(7) 0.0317(2) Uani 1 1 d . . .
O5 O 0.10999(11) -0.32216(16) 0.05563(8) 0.0366(3) Uani 1 1 d . . .
H5A H 0.082(2) -0.354(3) -0.0048(16) 0.047(5) Uiso 1 1 d . . .
C1 C 0.26153(15) 0.04314(18) 0.03898(10) 0.0268(3) Uani 1 1 d . . .
H1A H 0.2299 0.1588 0.0272 0.032 Uiso 1 1 calc R . .
C2 C 0.28042(14) -0.01673(19) 0.13621(10) 0.0260(3) Uani 1 1 d . . .
C3 C 0.32107(16) -0.20149(19) 0.16061(10) 0.0299(3) Uani 1 1 d . . .
H3A H 0.2775 -0.2387 0.2218 0.036 Uiso 1 1 calc R . .
H3B H 0.4299 -0.2114 0.1789 0.036 Uiso 1 1 calc R . .
C4 C 0.26675(15) -0.31848(19) 0.06929(10) 0.0283(3) Uani 1 1 d . . .
H4A H 0.3060 -0.4370 0.0855 0.034 Uiso 1 1 calc R . .
C5 C 0.31834(14) -0.25389(18) -0.03023(10) 0.0241(3) Uani 1 1 d . . .
H5B H 0.4265 -0.2768 -0.0259 0.029 Uiso 1 1 calc R . .
C6 C 0.28729(14) -0.06146(18) -0.05252(10) 0.0247(3) Uani 1 1 d . . .
H6A H 0.3758 -0.0124 -0.0778 0.030 Uiso 1 1 calc R . .
C7 C 0.15908(15) -0.05996(19) -0.14488(10) 0.0281(3) Uani 1 1 d . . .
H7A H 0.0623 -0.0663 -0.1207 0.034 Uiso 1 1 calc R . .
H7B H 0.1618 0.0444 -0.1881 0.034 Uiso 1 1 calc R . .
C8 C 0.18835(14) -0.22206(18) -0.20510(10) 0.0252(3) Uani 1 1 d . . .
H8A H 0.0946 -0.2626 -0.2488 0.030 Uiso 1 1 calc R . .
C9 C 0.30628(16) -0.5022(2) -0.14913(11) 0.0304(3) Uani 1 1 d . . .
H9A H 0.3146 -0.5841 -0.0902 0.036 Uiso 1 1 calc R . .
H9B H 0.4075 -0.4755 -0.1616 0.036 Uiso 1 1 calc R . .
C10 C 0.22080(15) -0.58526(18) -0.24513(11) 0.0272(3) Uani 1 1 d . . .
C11 C 0.07204(16) -0.6286(2) -0.25071(11) 0.0322(3) Uani 1 1 d . . .
H11A H 0.0240 -0.6091 -0.1924 0.039 Uiso 1 1 calc R . .
C12 C -0.00554(17) -0.6996(2) -0.34063(12) 0.0380(3) Uani 1 1 d . . .
H12A H -0.1071 -0.7275 -0.3441 0.046 Uiso 1 1 calc R . .
C13 C 0.06321(18) -0.7304(2) -0.42560(12) 0.0415(4) Uani 1 1 d . . .
H13A H 0.0092 -0.7796 -0.4872 0.050 Uiso 1 1 calc R . .
C14 C 0.21044(18) -0.6895(2) -0.42084(11) 0.0393(4) Uani 1 1 d . . .
H14A H 0.2584 -0.7114 -0.4790 0.047 Uiso 1 1 calc R . .
C15 C 0.28833(16) -0.6164(2) -0.33122(11) 0.0319(3) Uani 1 1 d . . .
H15A H 0.3895 -0.5872 -0.3287 0.038 Uiso 1 1 calc R . .
C16 C 0.30388(15) -0.18334(18) -0.27409(10) 0.0269(3) Uani 1 1 d . . .
C17 C 0.33202(18) -0.1090(2) -0.44755(11) 0.0369(4) Uani 1 1 d . . .
H17A H 0.4143 -0.0364 -0.4129 0.044 Uiso 1 1 calc R . .
H17B H 0.2737 -0.0406 -0.5041 0.044 Uiso 1 1 calc R . .
C18 C 0.39401(18) -0.2640(2) -0.49352(12) 0.0410(4) Uani 1 1 d . . .
H18A H 0.4569 -0.2273 -0.5435 0.062 Uiso 1 1 calc R . .
H18B H 0.3128 -0.3348 -0.5293 0.062 Uiso 1 1 calc R . .
H18C H 0.4529 -0.3312 -0.4378 0.062 Uiso 1 1 calc R . .
C19 C 0.26907(15) 0.09701(19) 0.22627(10) 0.0273(3) Uani 1 1 d . . .
C20 C 0.21064(17) 0.3723(2) 0.28153(11) 0.0356(3) Uani 1 1 d . . .
H20A H 0.1650 0.4800 0.2534 0.053 Uiso 1 1 calc R . .
H20B H 0.3129 0.3943 0.3146 0.053 Uiso 1 1 calc R . .
H20C H 0.1548 0.3256 0.3333 0.053 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 C8 1.4598(17) . ?
N1 C9 1.4643(18) . ?
N1 C5 1.4687(17) . ?
O1 C19 1.3384(18) . ?
O1 C20 1.4378(17) . ?
O2 C19 1.2109(17) . ?
O3 C16 1.1988(17) . ?
O4 C16 1.3345(16) . ?
O4 C17 1.4530(17) . ?
O5 C4 1.4189(17) . ?
O5 H5A 0.82(2) . ?
C1 C2 1.3312(19) . ?
C1 C6 1.4918(18) . ?
C1 H1A 0.9500 . ?
C2 C19 1.4847(19) . ?
C2 C3 1.506(2) . ?
C3 C4 1.5134(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5334(17) . ?
C4 H4A 1.0000 . ?
C5 C6 1.543(2) . ?
C5 H5B 1.0000 . ?
C6 C7 1.5354(19) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5314(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C16 1.5263(18) . ?
C8 H8A 1.0000 . ?
C9 C10 1.505(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3866(19) . ?
C10 C11 1.395(2) . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 C18 1.499(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 N1 C9 116.61(10) . . ?
C8 N1 C5 110.01(11) . . ?
C9 N1 C5 114.39(11) . . ?
C19 O1 C20 115.54(11) . . ?
C16 O4 C17 117.39(11) . . ?
C4 O5 H5A 105.7(13) . . ?
C2 C1 C6 123.58(13) . . ?
C2 C1 H1A 118.2 . . ?
C6 C1 H1A 118.2 . . ?
C1 C2 C19 121.65(13) . . ?
C1 C2 C3 121.53(13) . . ?
C19 C2 C3 116.76(12) . . ?
C2 C3 C4 111.78(11) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O5 C4 C3 107.81(11) . . ?
O5 C4 C5 110.36(11) . . ?
C3 C4 C5 110.92(12) . . ?
O5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C5 C4 109.33(11) . . ?
N1 C5 C6 104.95(10) . . ?
C4 C5 C6 113.81(11) . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C6 C7 114.70(11) . . ?
C1 C6 C5 115.36(11) . . ?
C7 C6 C5 104.36(11) . . ?
C1 C6 H6A 107.3 . . ?
C7 C6 H6A 107.3 . . ?
C5 C6 H6A 107.3 . . ?
C8 C7 C6 102.55(11) . . ?
C8 C7 H7A 111.3 . . ?
C6 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N1 C8 C16 114.72(11) . . ?
N1 C8 C7 101.99(10) . . ?
C16 C8 C7 109.56(12) . . ?
N1 C8 H8A 110.1 . . ?
C16 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N1 C9 C10 112.22(11) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 118.58(13) . . ?
C15 C10 C9 120.22(13) . . ?
C11 C10 C9 121.18(13) . . ?
C12 C11 C10 120.26(13) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 120.53(14) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 119.81(14) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 119.88(13) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C10 120.93(13) . . ?
C14 C15 H15A 119.5 . . ?
C10 C15 H15A 119.5 . . ?
O3 C16 O4 124.90(12) . . ?
O3 C16 C8 124.87(12) . . ?
O4 C16 C8 110.20(11) . . ?
O4 C17 C18 111.58(13) . . ?
O4 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O4 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 O1 123.49(13) . . ?
O2 C19 C2 123.21(14) . . ?
O1 C19 C2 113.30(12) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C19 173.35(12) . . . . ?
C6 C1 C2 C3 -3.9(2) . . . . ?
C1 C2 C3 C4 -27.40(19) . . . . ?
C19 C2 C3 C4 155.25(11) . . . . ?
C2 C3 C4 O5 -68.02(14) . . . . ?
C2 C3 C4 C5 52.91(16) . . . . ?
C8 N1 C5 C4 135.90(11) . . . . ?
C9 N1 C5 C4 -90.59(13) . . . . ?
C8 N1 C5 C6 13.45(12) . . . . ?
C9 N1 C5 C6 146.96(11) . . . . ?
O5 C4 C5 N1 -47.16(15) . . . . ?
C3 C4 C5 N1 -166.57(12) . . . . ?
O5 C4 C5 C6 69.81(15) . . . . ?
C3 C4 C5 C6 -49.60(15) . . . . ?
C2 C1 C6 C7 129.05(14) . . . . ?
C2 C1 C6 C5 7.71(19) . . . . ?
N1 C5 C6 C1 139.27(11) . . . . ?
C4 C5 C6 C1 19.77(16) . . . . ?
N1 C5 C6 C7 12.49(13) . . . . ?
C4 C5 C6 C7 -107.00(12) . . . . ?
C1 C6 C7 C8 -159.43(11) . . . . ?
C5 C6 C7 C8 -32.24(13) . . . . ?
C9 N1 C8 C16 -47.81(17) . . . . ?
C5 N1 C8 C16 84.57(13) . . . . ?
C9 N1 C8 C7 -166.14(11) . . . . ?
C5 N1 C8 C7 -33.76(12) . . . . ?
C6 C7 C8 N1 39.94(13) . . . . ?
C6 C7 C8 C16 -82.01(12) . . . . ?
C8 N1 C9 C10 -47.20(16) . . . . ?
C5 N1 C9 C10 -177.54(11) . . . . ?
N1 C9 C10 C15 122.74(14) . . . . ?
N1 C9 C10 C11 -55.68(18) . . . . ?
C15 C10 C11 C12 -0.5(2) . . . . ?
C9 C10 C11 C12 177.92(14) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 0.8(2) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C9 C10 C15 C14 -178.68(14) . . . . ?
C17 O4 C16 O3 -1.6(2) . . . . ?
C17 O4 C16 C8 176.78(12) . . . . ?
N1 C8 C16 O3 -35.8(2) . . . . ?
C7 C8 C16 O3 78.19(17) . . . . ?
N1 C8 C16 O4 145.82(12) . . . . ?
C7 C8 C16 O4 -100.20(13) . . . . ?
C16 O4 C17 C18 86.32(16) . . . . ?
C20 O1 C19 O2 6.10(18) . . . . ?
C20 O1 C19 C2 -173.53(11) . . . . ?
C1 C2 C19 O2 -166.65(13) . . . . ?
C3 C2 C19 O2 10.69(19) . . . . ?
C1 C2 C19 O1 12.98(17) . . . . ?
C3 C2 C19 O1 -169.68(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 995987'
