# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  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. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 922750'
#TrackingRef 'Compound11.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N O5'
_chemical_formula_weight         373.44
_chemical_absolute_configuration syn
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_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   7.6964(6)
_cell_length_b                   9.0385(9)
_cell_length_c                   28.1815(19)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1960.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1232
_cell_measurement_theta_min      3.1337
_cell_measurement_theta_max      74.5582
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.041
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         4461
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4426
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         74.74
_reflns_number_total             3150
_reflns_number_gt                2034
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_number_reflns         3150
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C8 C 0.8249(4) 0.4783(4) 0.15548(10) 0.0542(8) Uani 1 1 d . . .
O2 O 0.9254(3) 0.0881(3) 0.05326(9) 0.0800(7) Uani 1 1 d . . .
C13 C 0.7546(5) 0.7478(4) 0.17795(11) 0.0677(9) Uani 1 1 d . . .
C10 C 0.5977(4) 0.3198(4) 0.11037(10) 0.0560(8) Uani 1 1 d . . .
C9 C 0.6705(4) 0.4774(4) 0.11991(10) 0.0550(8) Uani 1 1 d . . .
O1 O 0.5998(4) -0.0703(3) 0.02597(8) 0.0880(9) Uani 1 1 d . . .
C4 C 0.7573(5) 0.1308(4) 0.06035(11) 0.0640(9) Uani 1 1 d . . .
C5 C 0.7521(4) 0.2322(4) 0.09518(10) 0.0572(8) Uani 1 1 d . . .
C6 C 0.9253(4) 0.2553(4) 0.10888(11) 0.0633(8) Uani 1 1 d . . .
N1 N 1.0326(4) 0.1695(4) 0.08533(11) 0.0813(9) Uani 1 1 d . . .
C3 C 0.6145(5) 0.0899(4) 0.02859(13) 0.0687(10) Uani 1 1 d . . .
C14 C 0.8920(5) 0.6360(4) 0.16258(10) 0.0586(8) Uani 1 1 d . . .
C11 C 0.5317(5) 0.5884(4) 0.13535(12) 0.0703(10) Uani 1 1 d . . .
H11A H 0.4401 0.5907 0.1117 0.084 Uiso 1 1 calc R . .
H11B H 0.4809 0.5556 0.1650 0.084 Uiso 1 1 calc R . .
C1 C 0.4705(5) 0.3126(4) 0.06800(11) 0.0672(9) Uani 1 1 d . . .
H1A H 0.3581 0.3497 0.0780 0.081 Uiso 1 1 calc R . .
H1B H 0.5129 0.3766 0.0429 0.081 Uiso 1 1 calc R . .
C7 C 0.9781(5) 0.3746(4) 0.14212(12) 0.0686(9) Uani 1 1 d . . .
H7A H 1.0697 0.4329 0.1276 0.082 Uiso 1 1 calc R . .
H7B H 1.0246 0.3304 0.1708 0.082 Uiso 1 1 calc R . .
C19 C 0.5117(5) 0.2524(4) 0.15475(11) 0.0748(10) Uani 1 1 d . . .
H19A H 0.4798 0.1516 0.1484 0.112 Uiso 1 1 calc R . .
H19B H 0.4097 0.3082 0.1627 0.112 Uiso 1 1 calc R . .
H19C H 0.5920 0.2553 0.1808 0.112 Uiso 1 1 calc R . .
O3 O 0.9940(4) 0.9127(3) 0.20491(11) 0.1050(10) Uani 1 1 d . . .
C15 C 1.0466(5) 0.6458(4) 0.19710(12) 0.0759(10) Uani 1 1 d . . .
H15A H 1.0182 0.5890 0.2253 0.091 Uiso 1 1 calc R . .
H15B H 1.1460 0.5988 0.1823 0.091 Uiso 1 1 calc R . .
C2 C 0.4481(5) 0.1547(4) 0.04820(13) 0.0707(10) Uani 1 1 d . . .
H2A H 0.4052 0.0909 0.0733 0.085 Uiso 1 1 calc R . .
H2B H 0.3613 0.1564 0.0232 0.085 Uiso 1 1 calc R . .
C12 C 0.6036(6) 0.7442(4) 0.14180(13) 0.0795(11) Uani 1 1 d . . .
H12A H 0.5114 0.8091 0.1526 0.095 Uiso 1 1 calc R . .
H12B H 0.6445 0.7811 0.1115 0.095 Uiso 1 1 calc R . .
O4 O 1.2318(4) 0.8202(4) 0.23330(12) 0.1254(12) Uani 1 1 d . . .
C20 C 0.6080(6) -0.1377(4) -0.01410(14) 0.0797(11) Uani 1 1 d . . .
C17 C 0.8398(6) 0.8989(5) 0.17618(15) 0.0971(14) Uani 1 1 d . . .
H17A H 0.8699 0.9209 0.1435 0.116 Uiso 1 1 calc R . .
H17B H 0.7561 0.9724 0.1865 0.116 Uiso 1 1 calc R . .
C16 C 1.0991(6) 0.7972(5) 0.21228(13) 0.0857(12) Uani 1 1 d . . .
C21 C 0.6020(7) -0.3009(4) -0.01184(17) 0.1061(15) Uani 1 1 d . . .
H21A H 0.4936 -0.3316 0.0019 0.159 Uiso 1 1 calc R . .
H21B H 0.6962 -0.3363 0.0074 0.159 Uiso 1 1 calc R . .
H21C H 0.6122 -0.3409 -0.0433 0.159 Uiso 1 1 calc R . .
C18 C 0.6850(6) 0.7189(5) 0.22859(11) 0.0926(14) Uani 1 1 d . . .
H18A H 0.7779 0.7301 0.2511 0.139 Uiso 1 1 calc R . .
H18B H 0.6396 0.6201 0.2304 0.139 Uiso 1 1 calc R . .
H18C H 0.5945 0.7885 0.2357 0.139 Uiso 1 1 calc R . .
O5 O 0.6221(9) -0.0722(4) -0.04930(11) 0.202(3) Uani 1 1 d . . .
H8 H 0.769(4) 0.443(3) 0.1864(11) 0.065(9) Uiso 1 1 d . . .
H9 H 0.710(4) 0.516(4) 0.0893(11) 0.062(9) Uiso 1 1 d . . .
H3 H 0.638(4) 0.121(3) -0.0023(11) 0.060(9) Uiso 1 1 d . . .
H14 H 0.937(3) 0.669(3) 0.1298(10) 0.055(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C8 0.0559(18) 0.0569(19) 0.0497(15) -0.0004(15) 0.0041(15) 0.0104(15)
O2 0.0782(17) 0.0681(15) 0.0938(16) -0.0187(14) 0.0194(15) 0.0072(14)
C13 0.084(2) 0.061(2) 0.0586(17) -0.0111(17) -0.0103(17) 0.015(2)
C10 0.0527(16) 0.0635(19) 0.0519(15) 0.0000(15) 0.0037(14) 0.0076(16)
C9 0.0626(18) 0.0531(19) 0.0493(15) -0.0024(15) 0.0028(15) 0.0096(16)
O1 0.148(3) 0.0481(12) 0.0680(13) -0.0061(12) 0.0132(16) -0.0076(17)
C4 0.071(2) 0.061(2) 0.0607(17) 0.0002(17) 0.0131(17) -0.0015(19)
C5 0.0639(19) 0.0543(18) 0.0532(15) 0.0012(15) 0.0119(15) 0.0119(17)
C6 0.0579(19) 0.062(2) 0.0696(18) -0.0005(18) 0.0082(16) 0.0096(17)
N1 0.0700(18) 0.0720(19) 0.102(2) -0.0223(18) 0.0135(17) 0.0104(17)
C3 0.100(3) 0.0467(17) 0.0597(18) -0.0013(16) 0.011(2) -0.004(2)
C14 0.073(2) 0.0577(19) 0.0453(15) -0.0037(15) -0.0021(16) 0.0085(17)
C11 0.068(2) 0.075(2) 0.0679(19) -0.0105(18) -0.0130(17) 0.020(2)
C1 0.069(2) 0.069(2) 0.0637(17) -0.0065(17) -0.0047(16) -0.0004(19)
C7 0.062(2) 0.066(2) 0.077(2) -0.0052(19) -0.0046(17) 0.0124(18)
C19 0.074(2) 0.084(3) 0.0666(19) 0.0047(19) 0.0162(17) -0.001(2)
O3 0.121(2) 0.083(2) 0.111(2) -0.0314(18) -0.0322(19) 0.004(2)
C15 0.076(2) 0.082(3) 0.070(2) -0.016(2) -0.0137(19) 0.007(2)
C2 0.075(2) 0.064(2) 0.073(2) -0.0117(18) -0.0051(18) -0.0026(19)
C12 0.094(3) 0.072(2) 0.072(2) -0.013(2) -0.023(2) 0.023(2)
O4 0.109(2) 0.138(3) 0.130(2) -0.056(2) -0.032(2) -0.002(2)
C20 0.106(3) 0.065(2) 0.069(2) -0.003(2) -0.012(2) -0.017(2)
C17 0.129(4) 0.064(3) 0.097(3) -0.018(2) -0.031(3) 0.006(3)
C16 0.088(3) 0.092(3) 0.076(2) -0.026(2) -0.016(2) 0.000(3)
C21 0.132(4) 0.056(2) 0.131(3) -0.021(2) -0.010(3) -0.009(3)
C18 0.097(3) 0.122(4) 0.0590(19) -0.022(2) 0.0030(19) 0.023(3)
O5 0.437(9) 0.088(2) 0.083(2) -0.0153(19) -0.012(4) -0.062(4)
_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
C8 C14 1.529(4) . ?
C8 C7 1.552(4) . ?
C8 C9 1.555(4) . ?
C8 H8 1.02(3) . ?
O2 C4 1.365(4) . ?
O2 N1 1.428(4) . ?
C13 C17 1.516(5) . ?
C13 C14 1.525(4) . ?
C13 C12 1.545(5) . ?
C13 C18 1.546(5) . ?
C10 C5 1.490(4) . ?
C10 C19 1.541(4) . ?
C10 C1 1.545(4) . ?
C10 C9 1.554(4) . ?
C9 C11 1.529(4) . ?
C9 H9 0.98(3) . ?
O1 C20 1.285(4) . ?
O1 C3 1.454(4) . ?
C4 C5 1.344(4) . ?
C4 C3 1.465(5) . ?
C5 C6 1.403(5) . ?
C6 N1 1.313(4) . ?
C6 C7 1.486(5) . ?
C3 C2 1.513(5) . ?
C3 H3 0.93(3) . ?
C14 C15 1.539(4) . ?
C14 H14 1.03(3) . ?
C11 C12 1.524(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 C2 1.542(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O3 C16 1.336(5) . ?
O3 C17 1.442(5) . ?
C15 C16 1.490(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O4 C16 1.199(4) . ?
C20 O5 1.160(4) . ?
C20 C21 1.477(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C14 C8 C7 109.8(3) . . ?
C14 C8 C9 110.3(3) . . ?
C7 C8 C9 114.9(2) . . ?
C14 C8 H8 108.5(18) . . ?
C7 C8 H8 110.0(18) . . ?
C9 C8 H8 103.0(18) . . ?
C4 O2 N1 108.0(2) . . ?
C17 C13 C14 106.7(3) . . ?
C17 C13 C12 108.8(3) . . ?
C14 C13 C12 108.7(3) . . ?
C17 C13 C18 109.4(3) . . ?
C14 C13 C18 113.0(3) . . ?
C12 C13 C18 110.2(3) . . ?
C5 C10 C19 111.5(3) . . ?
C5 C10 C1 105.1(3) . . ?
C19 C10 C1 109.8(3) . . ?
C5 C10 C9 104.4(3) . . ?
C19 C10 C9 112.1(3) . . ?
C1 C10 C9 113.6(3) . . ?
C11 C9 C10 113.5(3) . . ?
C11 C9 C8 110.3(2) . . ?
C10 C9 C8 113.1(3) . . ?
C11 C9 H9 103.8(19) . . ?
C10 C9 H9 106.5(19) . . ?
C8 C9 H9 109.0(18) . . ?
C20 O1 C3 120.9(3) . . ?
C5 C4 O2 109.1(3) . . ?
C5 C4 C3 126.6(3) . . ?
O2 C4 C3 123.4(3) . . ?
C4 C5 C6 105.9(3) . . ?
C4 C5 C10 126.6(3) . . ?
C6 C5 C10 126.9(3) . . ?
N1 C6 C5 111.8(3) . . ?
N1 C6 C7 125.1(3) . . ?
C5 C6 C7 122.7(3) . . ?
C6 N1 O2 105.1(3) . . ?
O1 C3 C4 109.9(3) . . ?
O1 C3 C2 109.7(3) . . ?
C4 C3 C2 108.3(3) . . ?
O1 C3 H3 105.5(19) . . ?
C4 C3 H3 110.6(19) . . ?
C2 C3 H3 113(2) . . ?
C13 C14 C8 114.9(3) . . ?
C13 C14 C15 108.6(3) . . ?
C8 C14 C15 113.4(3) . . ?
C13 C14 H14 107.3(16) . . ?
C8 C14 H14 105.5(16) . . ?
C15 C14 H14 106.7(16) . . ?
C12 C11 C9 112.7(3) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C2 C1 C10 112.9(3) . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C10 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C6 C7 C8 112.6(3) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 O3 C17 121.2(3) . . ?
C16 C15 C14 116.3(3) . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C3 C2 C1 113.3(3) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C11 C12 C13 111.8(3) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O5 C20 O1 120.9(4) . . ?
O5 C20 C21 123.3(4) . . ?
O1 C20 C21 115.8(4) . . ?
O3 C17 C13 114.5(3) . . ?
O3 C17 H17A 108.6 . . ?
C13 C17 H17A 108.6 . . ?
O3 C17 H17B 108.6 . . ?
C13 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O4 C16 O3 117.2(4) . . ?
O4 C16 C15 122.1(4) . . ?
O3 C16 C15 120.6(4) . . ?
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 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5 C10 C9 C11 179.0(2) . . . . ?
C19 C10 C9 C11 -60.2(3) . . . . ?
C1 C10 C9 C11 65.0(3) . . . . ?
C5 C10 C9 C8 -54.4(3) . . . . ?
C19 C10 C9 C8 66.4(3) . . . . ?
C1 C10 C9 C8 -168.3(3) . . . . ?
C14 C8 C9 C11 -52.6(3) . . . . ?
C7 C8 C9 C11 -177.3(3) . . . . ?
C14 C8 C9 C10 179.0(3) . . . . ?
C7 C8 C9 C10 54.3(4) . . . . ?
N1 O2 C4 C5 -0.8(4) . . . . ?
N1 O2 C4 C3 169.3(3) . . . . ?
O2 C4 C5 C6 1.7(4) . . . . ?
C3 C4 C5 C6 -167.9(3) . . . . ?
O2 C4 C5 C10 172.6(3) . . . . ?
C3 C4 C5 C10 3.0(6) . . . . ?
C19 C10 C5 C4 99.1(4) . . . . ?
C1 C10 C5 C4 -19.8(4) . . . . ?
C9 C10 C5 C4 -139.6(3) . . . . ?
C19 C10 C5 C6 -91.8(4) . . . . ?
C1 C10 C5 C6 149.3(3) . . . . ?
C9 C10 C5 C6 29.4(4) . . . . ?
C4 C5 C6 N1 -2.2(4) . . . . ?
C10 C5 C6 N1 -173.1(3) . . . . ?
C4 C5 C6 C7 171.5(3) . . . . ?
C10 C5 C6 C7 0.6(5) . . . . ?
C5 C6 N1 O2 1.7(4) . . . . ?
C7 C6 N1 O2 -171.8(3) . . . . ?
C4 O2 N1 C6 -0.6(4) . . . . ?
C20 O1 C3 C4 -123.5(4) . . . . ?
C20 O1 C3 C2 117.5(4) . . . . ?
C5 C4 C3 O1 -132.6(4) . . . . ?
O2 C4 C3 O1 59.2(4) . . . . ?
C5 C4 C3 C2 -12.7(5) . . . . ?
O2 C4 C3 C2 179.1(3) . . . . ?
C17 C13 C14 C8 -172.1(3) . . . . ?
C12 C13 C14 C8 -54.9(4) . . . . ?
C18 C13 C14 C8 67.7(4) . . . . ?
C17 C13 C14 C15 59.8(4) . . . . ?
C12 C13 C14 C15 177.0(3) . . . . ?
C18 C13 C14 C15 -60.5(4) . . . . ?
C7 C8 C14 C13 -177.5(2) . . . . ?
C9 C8 C14 C13 54.9(3) . . . . ?
C7 C8 C14 C15 -51.9(3) . . . . ?
C9 C8 C14 C15 -179.5(3) . . . . ?
C10 C9 C11 C12 -176.7(3) . . . . ?
C8 C9 C11 C12 55.2(4) . . . . ?
C5 C10 C1 C2 46.9(4) . . . . ?
C19 C10 C1 C2 -73.1(4) . . . . ?
C9 C10 C1 C2 160.5(3) . . . . ?
N1 C6 C7 C8 167.1(3) . . . . ?
C5 C6 C7 C8 -5.8(5) . . . . ?
C14 C8 C7 C6 -146.2(3) . . . . ?
C9 C8 C7 C6 -21.2(4) . . . . ?
C13 C14 C15 C16 -40.8(4) . . . . ?
C8 C14 C15 C16 -169.7(3) . . . . ?
O1 C3 C2 C1 160.5(3) . . . . ?
C4 C3 C2 C1 40.5(4) . . . . ?
C10 C1 C2 C3 -62.4(4) . . . . ?
C9 C11 C12 C13 -56.9(4) . . . . ?
C17 C13 C12 C11 170.2(3) . . . . ?
C14 C13 C12 C11 54.4(4) . . . . ?
C18 C13 C12 C11 -69.9(4) . . . . ?
C3 O1 C20 O5 -2.3(8) . . . . ?
C3 O1 C20 C21 176.4(4) . . . . ?
C16 O3 C17 C13 31.7(5) . . . . ?
C14 C13 C17 O3 -57.1(4) . . . . ?
C12 C13 C17 O3 -174.2(3) . . . . ?
C18 C13 C17 O3 65.4(4) . . . . ?
C17 O3 C16 O4 174.1(4) . . . . ?
C17 O3 C16 C15 -9.2(6) . . . . ?
C14 C15 C16 O4 -168.9(4) . . . . ?
C14 C15 C16 O3 14.6(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.040


data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 922751'
#TrackingRef 'Compound12.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 N O5'
_chemical_formula_weight         349.42
_chemical_absolute_configuration syn
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   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   7.6411(3)
_cell_length_b                   8.3284(4)
_cell_length_c                   27.4713(13)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1748.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      2.9600
_cell_measurement_theta_max      29.0344
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         6454
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5375
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2871
_reflns_number_gt                2469
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0427P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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   -1.1(14)
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.4936(3) -0.4143(3) 0.87206(9) 0.0400(6) Uani 1 1 d . . .
H1A H 0.5716 -0.4966 0.8844 0.048 Uiso 1 1 calc R . .
H1B H 0.4172 -0.3815 0.8985 0.048 Uiso 1 1 calc R . .
C2 C 0.3827(3) -0.4848(3) 0.83082(9) 0.0422(6) Uani 1 1 d . . .
H2A H 0.3260 -0.5816 0.8425 0.051 Uiso 1 1 calc R . .
H2B H 0.4595 -0.5150 0.8042 0.051 Uiso 1 1 calc R . .
C3 C 0.2426(4) -0.3699(3) 0.81138(9) 0.0409(7) Uani 1 1 d . . .
C4 C 0.3231(3) -0.2072(3) 0.80911(8) 0.0356(6) Uani 1 1 d . . .
C5 C 0.4749(3) -0.1630(3) 0.82922(8) 0.0309(6) Uani 1 1 d . . .
C6 C 0.4754(3) 0.0051(3) 0.82796(8) 0.0352(6) Uani 1 1 d . . .
C7 C 0.6097(3) 0.1036(3) 0.85357(9) 0.0417(6) Uani 1 1 d . . .
H7A H 0.5525 0.1716 0.8774 0.050 Uiso 1 1 calc R . .
H7B H 0.6679 0.1726 0.8302 0.050 Uiso 1 1 calc R . .
C8 C 0.7485(3) -0.0026(3) 0.87961(8) 0.0302(5) Uani 1 1 d . . .
C9 C 0.6731(3) -0.1643(3) 0.89787(8) 0.0292(6) Uani 1 1 d . . .
C10 C 0.6028(3) -0.2686(3) 0.85525(8) 0.0309(6) Uani 1 1 d . . .
C11 C 0.8052(3) -0.2547(3) 0.92942(8) 0.0407(6) Uani 1 1 d . . .
H11A H 0.7494 -0.3496 0.9428 0.049 Uiso 1 1 calc R . .
H11B H 0.9016 -0.2901 0.9091 0.049 Uiso 1 1 calc R . .
C12 C 0.8771(4) -0.1542(3) 0.97088(9) 0.0437(7) Uani 1 1 d . . .
H12A H 0.9614 -0.2171 0.9892 0.052 Uiso 1 1 calc R . .
H12B H 0.7824 -0.1253 0.9927 0.052 Uiso 1 1 calc R . .
C13 C 0.9651(3) -0.0018(3) 0.95208(8) 0.0346(6) Uani 1 1 d . . .
C14 C 0.8305(3) 0.0921(3) 0.92192(8) 0.0323(6) Uani 1 1 d . . .
C15 C 0.9118(4) 0.2510(3) 0.90580(9) 0.0455(7) Uani 1 1 d . . .
H15A H 0.9739 0.2321 0.8756 0.055 Uiso 1 1 calc R . .
H15B H 0.8173 0.3252 0.8987 0.055 Uiso 1 1 calc R . .
C16 C 1.0346(4) 0.3321(4) 0.94017(11) 0.0481(7) Uani 1 1 d . . .
C17 C 1.0085(3) 0.1036(3) 0.99524(8) 0.0472(7) Uani 1 1 d . . .
H17A H 0.9030 0.1203 1.0142 0.057 Uiso 1 1 calc R . .
H17B H 1.0921 0.0479 1.0158 0.057 Uiso 1 1 calc R . .
C18 C 1.1322(3) -0.0413(4) 0.92385(10) 0.0538(8) Uani 1 1 d . . .
H18A H 1.1919 0.0565 0.9156 0.081 Uiso 1 1 calc R . .
H18B H 1.1026 -0.0981 0.8946 0.081 Uiso 1 1 calc R . .
H18C H 1.2071 -0.1070 0.9436 0.081 Uiso 1 1 calc R . .
C19 C 0.7513(3) -0.3244(4) 0.82126(9) 0.0460(7) Uani 1 1 d . . .
H19A H 0.7021 -0.3723 0.7926 0.069 Uiso 1 1 calc R . .
H19B H 0.8228 -0.4017 0.8379 0.069 Uiso 1 1 calc R . .
H19C H 0.8217 -0.2337 0.8122 0.069 Uiso 1 1 calc R . .
N1 N 0.3345(3) 0.0617(3) 0.80687(8) 0.0491(6) Uani 1 1 d . . .
O1 O 0.1752(3) -0.4146(3) 0.76550(7) 0.0530(5) Uani 1 1 d . . .
O2 O 0.2333(2) -0.0762(2) 0.79407(6) 0.0495(5) Uani 1 1 d . . .
O3 O 1.0803(3) 0.2585(3) 0.98196(7) 0.0608(6) Uani 1 1 d . . .
O4 O 1.1008(3) 0.4604(3) 0.93193(8) 0.0714(7) Uani 1 1 d . . .
O5 O 0.0484(3) -0.7113(3) 0.78797(8) 0.0521(6) Uani 1 1 d . . .
H9 H 0.568(3) -0.141(2) 0.9176(7) 0.025(6) Uiso 1 1 d . . .
H8 H 0.837(3) -0.020(3) 0.8579(7) 0.029(6) Uiso 1 1 d . . .
H14 H 0.734(3) 0.115(2) 0.9438(6) 0.019(5) Uiso 1 1 d . . .
H5A H -0.015(4) -0.761(4) 0.7716(10) 0.056(11) Uiso 1 1 d . . .
H3 H 0.140(4) -0.361(3) 0.8362(9) 0.052(8) Uiso 1 1 d . . .
H1 H 0.121(4) -0.508(4) 0.7699(10) 0.069(11) Uiso 1 1 d . . .
H5B H 0.137(4) -0.775(4) 0.7922(11) 0.064(11) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0364(13) 0.0349(14) 0.0486(14) 0.0086(13) -0.0115(12) 0.0002(13)
C2 0.0405(14) 0.0352(15) 0.0508(14) 0.0046(13) -0.0132(13) -0.0025(13)
C3 0.0415(15) 0.0406(16) 0.0406(14) 0.0018(13) -0.0124(14) -0.0030(14)
C4 0.0384(13) 0.0308(14) 0.0376(13) 0.0022(12) -0.0098(12) 0.0063(13)
C5 0.0306(13) 0.0339(15) 0.0282(11) 0.0010(12) -0.0051(11) 0.0006(11)
C6 0.0381(13) 0.0340(14) 0.0335(12) 0.0048(12) -0.0110(12) -0.0006(13)
C7 0.0447(15) 0.0352(16) 0.0451(13) 0.0064(13) -0.0148(12) 0.0011(14)
C8 0.0282(11) 0.0350(14) 0.0275(11) 0.0016(11) -0.0025(11) -0.0012(12)
C9 0.0263(12) 0.0346(14) 0.0266(11) 0.0050(10) 0.0009(11) 0.0019(11)
C10 0.0251(11) 0.0343(14) 0.0333(12) 0.0007(11) -0.0035(10) 0.0037(12)
C11 0.0380(14) 0.0390(16) 0.0449(14) 0.0090(13) -0.0114(12) -0.0004(13)
C12 0.0447(15) 0.0499(17) 0.0367(13) 0.0096(13) -0.0114(12) 0.0009(14)
C13 0.0281(12) 0.0445(15) 0.0314(12) 0.0025(12) -0.0040(11) 0.0023(13)
C14 0.0284(12) 0.0388(15) 0.0298(12) -0.0015(12) 0.0013(11) 0.0019(13)
C15 0.0489(15) 0.0430(17) 0.0448(14) 0.0007(13) -0.0157(12) -0.0048(15)
C16 0.0440(15) 0.0397(17) 0.0606(18) -0.0059(15) -0.0097(15) 0.0002(15)
C17 0.0446(16) 0.0578(19) 0.0393(13) 0.0024(14) -0.0135(13) -0.0037(16)
C18 0.0354(14) 0.066(2) 0.0600(17) -0.0023(15) 0.0014(13) 0.0049(15)
C19 0.0385(13) 0.0544(18) 0.0451(14) -0.0101(13) 0.0023(13) 0.0050(14)
N1 0.0557(14) 0.0314(13) 0.0604(13) 0.0038(11) -0.0294(12) -0.0009(12)
O1 0.0571(13) 0.0416(12) 0.0603(12) 0.0011(10) -0.0279(10) -0.0069(12)
O2 0.0473(10) 0.0362(10) 0.0651(12) 0.0048(10) -0.0298(10) 0.0032(10)
O3 0.0694(14) 0.0592(13) 0.0539(11) -0.0029(11) -0.0253(10) -0.0159(12)
O4 0.0713(15) 0.0492(14) 0.0938(16) 0.0035(12) -0.0320(13) -0.0170(13)
O5 0.0512(13) 0.0483(14) 0.0567(12) -0.0103(11) -0.0145(11) 0.0002(12)
_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 1.531(3) . ?
C1 C10 1.543(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.532(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.411(3) . ?
C3 C4 1.489(4) . ?
C3 H3 1.04(3) . ?
C4 C5 1.337(3) . ?
C4 O2 1.354(3) . ?
C5 C6 1.400(3) . ?
C5 C10 1.497(3) . ?
C6 N1 1.310(3) . ?
C6 C7 1.490(3) . ?
C7 C8 1.555(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.538(3) . ?
C8 C9 1.548(3) . ?
C8 H8 0.91(2) . ?
C9 C11 1.529(3) . ?
C9 C10 1.554(3) . ?
C9 H9 0.99(2) . ?
C10 C19 1.541(3) . ?
C11 C12 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.526(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.512(3) . ?
C13 C18 1.530(3) . ?
C13 C14 1.535(3) . ?
C14 C15 1.527(4) . ?
C14 H14 0.97(2) . ?
C15 C16 1.493(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O4 1.204(3) . ?
C16 O3 1.347(3) . ?
C17 O3 1.449(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 O2 1.429(3) . ?
O1 H1 0.89(3) . ?
O5 H5A 0.78(3) . ?
O5 H5B 0.87(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 112.3(2) . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 113.9(2) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C4 110.7(2) . . ?
O1 C3 C2 113.7(2) . . ?
C4 C3 C2 107.1(2) . . ?
O1 C3 H3 109.3(14) . . ?
C4 C3 H3 106.0(15) . . ?
C2 C3 H3 109.8(14) . . ?
C5 C4 O2 110.1(2) . . ?
C5 C4 C3 126.3(2) . . ?
O2 C4 C3 122.5(2) . . ?
C4 C5 C6 105.5(2) . . ?
C4 C5 C10 127.0(2) . . ?
C6 C5 C10 126.7(2) . . ?
N1 C6 C5 111.6(2) . . ?
N1 C6 C7 125.2(2) . . ?
C5 C6 C7 122.7(2) . . ?
C6 C7 C8 111.9(2) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C14 C8 C9 110.67(18) . . ?
C14 C8 C7 109.5(2) . . ?
C9 C8 C7 112.97(19) . . ?
C14 C8 H8 105.9(13) . . ?
C9 C8 H8 110.4(15) . . ?
C7 C8 H8 107.1(13) . . ?
C11 C9 C8 111.48(19) . . ?
C11 C9 C10 112.4(2) . . ?
C8 C9 C10 111.77(18) . . ?
C11 C9 H9 108.9(12) . . ?
C8 C9 H9 108.1(12) . . ?
C10 C9 H9 103.9(12) . . ?
C5 C10 C19 111.62(19) . . ?
C5 C10 C1 104.60(19) . . ?
C19 C10 C1 110.1(2) . . ?
C5 C10 C9 104.90(19) . . ?
C19 C10 C9 111.72(19) . . ?
C1 C10 C9 113.63(18) . . ?
C12 C11 C9 113.2(2) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.4(2) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C17 C13 C12 108.30(19) . . ?
C17 C13 C18 109.8(2) . . ?
C12 C13 C18 111.1(2) . . ?
C17 C13 C14 105.9(2) . . ?
C12 C13 C14 108.1(2) . . ?
C18 C13 C14 113.3(2) . . ?
C15 C14 C13 109.0(2) . . ?
C15 C14 C8 113.01(19) . . ?
C13 C14 C8 114.8(2) . . ?
C15 C14 H14 108.6(12) . . ?
C13 C14 H14 106.0(11) . . ?
C8 C14 H14 105.0(11) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15A 107.9 . . ?
C14 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
C14 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
O4 C16 O3 117.1(3) . . ?
O4 C16 C15 123.2(3) . . ?
O3 C16 C15 119.7(3) . . ?
O3 C17 C13 113.7(2) . . ?
O3 C17 H17A 108.8 . . ?
C13 C17 H17A 108.8 . . ?
O3 C17 H17B 108.8 . . ?
C13 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 N1 O2 105.3(2) . . ?
C3 O1 H1 106.2(19) . . ?
C4 O2 N1 107.37(17) . . ?
C16 O3 C17 121.4(2) . . ?
H5A O5 H5B 104(3) . . ?
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
C10 C1 C2 C3 -64.0(3) . . . . ?
C1 C2 C3 O1 163.0(2) . . . . ?
C1 C2 C3 C4 40.4(3) . . . . ?
O1 C3 C4 C5 -136.8(3) . . . . ?
C2 C3 C4 C5 -12.3(4) . . . . ?
O1 C3 C4 O2 56.6(3) . . . . ?
C2 C3 C4 O2 -179.0(2) . . . . ?
O2 C4 C5 C6 2.1(3) . . . . ?
C3 C4 C5 C6 -165.9(3) . . . . ?
O2 C4 C5 C10 172.6(2) . . . . ?
C3 C4 C5 C10 4.6(4) . . . . ?
C4 C5 C6 N1 -1.9(3) . . . . ?
C10 C5 C6 N1 -172.5(2) . . . . ?
C4 C5 C6 C7 170.6(2) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
N1 C6 C7 C8 173.4(2) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C6 C7 C8 C14 -155.4(2) . . . . ?
C6 C7 C8 C9 -31.6(3) . . . . ?
C14 C8 C9 C11 -48.8(3) . . . . ?
C7 C8 C9 C11 -171.9(2) . . . . ?
C14 C8 C9 C10 -175.42(19) . . . . ?
C7 C8 C9 C10 61.4(3) . . . . ?
C4 C5 C10 C19 96.5(3) . . . . ?
C6 C5 C10 C19 -94.9(3) . . . . ?
C4 C5 C10 C1 -22.5(3) . . . . ?
C6 C5 C10 C1 146.1(2) . . . . ?
C4 C5 C10 C9 -142.3(2) . . . . ?
C6 C5 C10 C9 26.2(3) . . . . ?
C2 C1 C10 C5 49.2(2) . . . . ?
C2 C1 C10 C19 -70.8(2) . . . . ?
C2 C1 C10 C9 163.1(2) . . . . ?
C11 C9 C10 C5 179.10(19) . . . . ?
C8 C9 C10 C5 -54.7(2) . . . . ?
C11 C9 C10 C19 -59.8(3) . . . . ?
C8 C9 C10 C19 66.4(3) . . . . ?
C11 C9 C10 C1 65.4(3) . . . . ?
C8 C9 C10 C1 -168.36(19) . . . . ?
C8 C9 C11 C12 52.9(3) . . . . ?
C10 C9 C11 C12 179.3(2) . . . . ?
C9 C11 C12 C13 -58.0(3) . . . . ?
C11 C12 C13 C17 171.5(2) . . . . ?
C11 C12 C13 C18 -67.8(3) . . . . ?
C11 C12 C13 C14 57.2(3) . . . . ?
C17 C13 C14 C15 60.1(2) . . . . ?
C12 C13 C14 C15 175.96(19) . . . . ?
C18 C13 C14 C15 -60.4(3) . . . . ?
C17 C13 C14 C8 -172.0(2) . . . . ?
C12 C13 C14 C8 -56.1(3) . . . . ?
C18 C13 C14 C8 67.5(3) . . . . ?
C9 C8 C14 C15 178.4(2) . . . . ?
C7 C8 C14 C15 -56.5(3) . . . . ?
C9 C8 C14 C13 52.5(3) . . . . ?
C7 C8 C14 C13 177.70(19) . . . . ?
C13 C14 C15 C16 -35.4(3) . . . . ?
C8 C14 C15 C16 -164.2(2) . . . . ?
C14 C15 C16 O4 -177.1(3) . . . . ?
C14 C15 C16 O3 5.1(4) . . . . ?
C12 C13 C17 O3 -175.3(2) . . . . ?
C18 C13 C17 O3 63.1(3) . . . . ?
C14 C13 C17 O3 -59.5(3) . . . . ?
C5 C6 N1 O2 1.0(3) . . . . ?
C7 C6 N1 O2 -171.4(2) . . . . ?
C5 C4 O2 N1 -1.6(2) . . . . ?
C3 C4 O2 N1 167.0(2) . . . . ?
C6 N1 O2 C4 0.4(2) . . . . ?
O4 C16 O3 C17 -179.8(3) . . . . ?
C15 C16 O3 C17 -2.0(4) . . . . ?
C13 C17 O3 C16 30.8(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033