# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Goffredo Rosini'
_publ_contact_author_address     
;
Dipartimento di Chimica Organica "A. Mangini"
Alma Mater Studiorum - Universita di Bologna
Viale del Risorgimento, 4
Bologna
I-40136
ITALY
;

_publ_contact_author_email       GOFFREDO.ROSINI@UNIBO.IT

_publ_section_title              
;
p1,n1 Salts: Self Assembled Supramolecular Structures
Sequestering Racemates
;
loop_
_publ_author_name
'Goffredo Rosini'
'Claudia Ayoub'
'Valerio Borzatta'
'Emanuela Marotta'
'Andrea Mazzanti'
'Paolo Righi'

# Attachment 'p1n1.CIF'

data_compound_2
_database_code_depnum_ccdc_archive 'CCDC 276877'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N O2, C10 H15 O2'
_chemical_formula_sum            'C21 H33 N O4'
_chemical_formula_weight         363.48

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

_cell_length_a                   11.1297(6)
_cell_length_b                   13.4914(7)
_cell_length_c                   28.0333(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4209.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plates
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45793
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.50
_reflns_number_total             9681
_reflns_number_gt                7079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0567P)^2^+0.2527P] 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   -0.7(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9681
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.43252(13) 0.44235(11) 0.28609(5) 0.0419(3) Uani 1 1 d . . .
HN1 H 0.4918(18) 0.3943(17) 0.2992(7) 0.063 Uiso 1 1 d . . .
N1A N 0.91243(13) 0.58055(10) 0.29128(5) 0.0379(3) Uani 1 1 d . . .
HN1A H 0.9555(18) 0.6315(16) 0.3045(7) 0.057 Uiso 1 1 d . . .
O1 O 0.15186(15) 0.79095(11) 0.29996(5) 0.0678(4) Uani 1 1 d . . .
O2 O 0.07453(15) 0.67704(12) 0.34777(5) 0.0716(5) Uani 1 1 d . . .
O3 O 0.25713(12) 0.53646(10) 0.22371(4) 0.0479(3) Uani 1 1 d . . .
HO3 H 0.306(2) 0.5808(17) 0.2105(8) 0.072 Uiso 1 1 d . . .
O4 O 0.41504(13) 0.24546(10) 0.25200(5) 0.0561(4) Uani 1 1 d . . .
HO4 H 0.469(2) 0.234(2) 0.2734(9) 0.084 Uiso 1 1 d . . .
O1A O 0.59806(12) 0.18782(9) 0.30897(4) 0.0505(3) Uani 1 1 d . . .
O2A O 0.58703(14) 0.34083(10) 0.33812(5) 0.0597(4) Uani 1 1 d . . .
O3A O 0.76184(12) 0.46273(10) 0.23011(5) 0.0492(3) Uani 1 1 d . . .
HO3A H 0.779(2) 0.4056(19) 0.2189(8) 0.074 Uiso 1 1 d . . .
O4A O 0.95418(15) 0.77431(10) 0.25156(6) 0.0630(4) Uani 1 1 d . . .
HO4A H 1.021(2) 0.780(2) 0.2689(10) 0.094 Uiso 1 1 d . . .
C1 C 0.25274(18) 0.76146(14) 0.37184(7) 0.0516(5) Uani 1 1 d . . .
H1 H 0.3174 0.8016 0.3581 0.062 Uiso 1 1 calc R . .
C2 C 0.23631(18) 0.77539(15) 0.42484(7) 0.0536(5) Uani 1 1 d . . .
C3 C 0.29565(17) 0.68326(14) 0.40681(6) 0.0479(4) Uani 1 1 d . . .
H3 H 0.2456 0.6236 0.4082 0.057 Uiso 1 1 calc R . .
C4 C 0.42631(18) 0.66501(15) 0.41178(7) 0.0525(5) Uani 1 1 d . . .
H4 H 0.4770 0.7113 0.3977 0.063 Uiso 1 1 calc R . .
C5 C 0.47837(16) 0.59090(15) 0.43388(7) 0.0481(4) Uani 1 1 d . . .
C6 C 0.15157(19) 0.74066(14) 0.33798(7) 0.0520(5) Uani 1 1 d . . .
C7 C 0.4115(2) 0.51303(19) 0.46032(10) 0.0793(7) Uani 1 1 d . . .
H7A H 0.4332 0.5154 0.4934 0.119 Uiso 1 1 calc R . .
H7B H 0.4313 0.4491 0.4475 0.119 Uiso 1 1 calc R . .
H7C H 0.3267 0.5243 0.4571 0.119 Uiso 1 1 calc R . .
C8 C 0.61259(19) 0.57747(19) 0.43359(9) 0.0683(6) Uani 1 1 d . . .
H8A H 0.6411 0.5715 0.4658 0.102 Uiso 1 1 calc R . .
H8B H 0.6496 0.6338 0.4187 0.102 Uiso 1 1 calc R . .
H8C H 0.6327 0.5185 0.4161 0.102 Uiso 1 1 calc R . .
C9 C 0.3149(2) 0.85200(17) 0.44877(9) 0.0771(7) Uani 1 1 d . . .
H9A H 0.3886 0.8587 0.4313 0.116 Uiso 1 1 calc R . .
H9B H 0.3322 0.8314 0.4808 0.116 Uiso 1 1 calc R . .
H9C H 0.2738 0.9145 0.4494 0.116 Uiso 1 1 calc R . .
C10 C 0.1128(2) 0.7683(2) 0.44597(9) 0.0735(7) Uani 1 1 d . . .
H10A H 0.0697 0.8286 0.4398 0.110 Uiso 1 1 calc R . .
H10B H 0.1190 0.7583 0.4798 0.110 Uiso 1 1 calc R . .
H10C H 0.0707 0.7136 0.4319 0.110 Uiso 1 1 calc R . .
C11 C 0.42433(15) 0.42102(12) 0.23301(6) 0.0375(4) Uani 1 1 d . . .
H11 H 0.4786 0.4675 0.2169 0.045 Uiso 1 1 calc R . .
C12 C 0.29869(15) 0.43897(12) 0.21281(6) 0.0391(4) Uani 1 1 d . . .
H12 H 0.2442 0.3921 0.2285 0.047 Uiso 1 1 calc R . .
C13 C 0.29428(17) 0.41786(13) 0.15985(6) 0.0457(4) Uani 1 1 d . . .
C14 C 0.3721(2) 0.46319(17) 0.12826(7) 0.0606(5) Uani 1 1 d . . .
H14 H 0.4282 0.5088 0.1393 0.073 Uiso 1 1 calc R . .
C15 C 0.3665(3) 0.4406(2) 0.08023(9) 0.0899(9) Uani 1 1 d . . .
H15 H 0.4198 0.4705 0.0591 0.108 Uiso 1 1 calc R . .
C16 C 0.2831(4) 0.3745(3) 0.06349(11) 0.1121(14) Uani 1 1 d . . .
H16 H 0.2795 0.3599 0.0311 0.135 Uiso 1 1 calc R . .
C17 C 0.2058(3) 0.3303(3) 0.09429(13) 0.1104(12) Uani 1 1 d . . .
H17 H 0.1493 0.2855 0.0829 0.133 Uiso 1 1 calc R . .
C18 C 0.2104(2) 0.35139(18) 0.14242(9) 0.0747(7) Uani 1 1 d . . .
H18 H 0.1569 0.3208 0.1632 0.090 Uiso 1 1 calc R . .
C19 C 0.47372(17) 0.31741(14) 0.22440(6) 0.0474(4) Uani 1 1 d . . .
H19A H 0.4649 0.3009 0.1909 0.057 Uiso 1 1 calc R . .
H19B H 0.5588 0.3167 0.2319 0.057 Uiso 1 1 calc R . .
C20 C 0.4775(2) 0.54397(16) 0.29580(8) 0.0665(6) Uani 1 1 d . . .
H20A H 0.5486 0.5559 0.2773 0.100 Uiso 1 1 calc R . .
H20B H 0.4960 0.5503 0.3291 0.100 Uiso 1 1 calc R . .
H20C H 0.4168 0.5914 0.2873 0.100 Uiso 1 1 calc R . .
C21 C 0.32292(19) 0.4213(2) 0.31443(7) 0.0671(6) Uani 1 1 d . . .
H21A H 0.2957 0.3553 0.3078 0.101 Uiso 1 1 calc R . .
H21B H 0.2611 0.4678 0.3061 0.101 Uiso 1 1 calc R . .
H21C H 0.3410 0.4273 0.3478 0.101 Uiso 1 1 calc R . .
C1A C 0.74059(16) 0.23542(12) 0.36696(6) 0.0410(4) Uani 1 1 d . . .
H1A H 0.7964 0.1861 0.3540 0.049 Uiso 1 1 calc R . .
C2A C 0.73286(16) 0.23725(13) 0.42118(6) 0.0432(4) Uani 1 1 d . . .
C3A C 0.79932(16) 0.31735(13) 0.39483(6) 0.0433(4) Uani 1 1 d . . .
H3A H 0.7564 0.3807 0.3934 0.052 Uiso 1 1 calc R . .
C4A C 0.93126(17) 0.32736(15) 0.39740(7) 0.0515(5) Uani 1 1 d . . .
H4A H 0.9760 0.2826 0.3795 0.062 Uiso 1 1 calc R . .
C5A C 0.99215(17) 0.39275(16) 0.42227(7) 0.0533(5) Uani 1 1 d . . .
C6A C 0.63434(17) 0.25696(13) 0.33582(6) 0.0430(4) Uani 1 1 d . . .
C7A C 0.9336(3) 0.4680(2) 0.45302(10) 0.0914(9) Uani 1 1 d . . .
H7A1 H 0.9684 0.4659 0.4843 0.137 Uiso 1 1 calc R . .
H7A2 H 0.8491 0.4542 0.4551 0.137 Uiso 1 1 calc R . .
H7A3 H 0.9452 0.5327 0.4395 0.137 Uiso 1 1 calc R . .
C8A C 1.1265(2) 0.3971(2) 0.42065(10) 0.0820(8) Uani 1 1 d . . .
H8A1 H 1.1579 0.3941 0.4525 0.123 Uiso 1 1 calc R . .
H8A2 H 1.1513 0.4580 0.4059 0.123 Uiso 1 1 calc R . .
H8A3 H 1.1565 0.3421 0.4025 0.123 Uiso 1 1 calc R . .
C9A C 0.8064(2) 0.16186(16) 0.44793(8) 0.0648(6) Uani 1 1 d . . .
H9A1 H 0.8747 0.1431 0.4290 0.097 Uiso 1 1 calc R . .
H9A2 H 0.7581 0.1044 0.4543 0.097 Uiso 1 1 calc R . .
H9A3 H 0.8333 0.1900 0.4775 0.097 Uiso 1 1 calc R . .
C10A C 0.6159(2) 0.26364(19) 0.44482(7) 0.0659(6) Uani 1 1 d . . .
H10D H 0.5709 0.2043 0.4510 0.099 Uiso 1 1 calc R . .
H10E H 0.5704 0.3063 0.4242 0.099 Uiso 1 1 calc R . .
H10F H 0.6317 0.2972 0.4744 0.099 Uiso 1 1 calc R . .
C11A C 0.87074(15) 0.61258(12) 0.24212(6) 0.0373(4) Uani 1 1 d . . .
H11A H 0.7935 0.6464 0.2461 0.045 Uiso 1 1 calc R . .
C12A C 0.84954(15) 0.52451(12) 0.20861(6) 0.0398(4) Uani 1 1 d . . .
H12A H 0.9246 0.4872 0.2051 0.048 Uiso 1 1 calc R . .
C13A C 0.80950(16) 0.56086(13) 0.16016(6) 0.0433(4) Uani 1 1 d . . .
C14A C 0.8842(2) 0.55496(17) 0.12096(7) 0.0599(5) Uani 1 1 d . . .
H14A H 0.9597 0.5261 0.1238 0.072 Uiso 1 1 calc R . .
C15A C 0.8464(2) 0.5924(2) 0.07692(8) 0.0758(7) Uani 1 1 d . . .
H15A H 0.8968 0.5880 0.0505 0.091 Uiso 1 1 calc R . .
C16A C 0.7369(3) 0.6349(2) 0.07251(8) 0.0763(7) Uani 1 1 d . . .
H16A H 0.7127 0.6604 0.0432 0.092 Uiso 1 1 calc R . .
C17A C 0.6614(2) 0.64055(19) 0.11102(8) 0.0720(6) Uani 1 1 d . . .
H17A H 0.5860 0.6696 0.1079 0.086 Uiso 1 1 calc R . .
C18A C 0.69764(19) 0.60292(16) 0.15465(7) 0.0573(5) Uani 1 1 d . . .
H18A H 0.6457 0.6061 0.1806 0.069 Uiso 1 1 calc R . .
C19A C 0.95895(19) 0.68806(14) 0.22338(6) 0.0510(5) Uani 1 1 d . . .
H19C H 1.0395 0.6607 0.2241 0.061 Uiso 1 1 calc R . .
H19D H 0.9395 0.7043 0.1906 0.061 Uiso 1 1 calc R . .
C20A C 0.99596(18) 0.49462(15) 0.29174(8) 0.0565(5) Uani 1 1 d . . .
H20D H 1.0600 0.5061 0.2695 0.085 Uiso 1 1 calc R . .
H20E H 0.9531 0.4357 0.2829 0.085 Uiso 1 1 calc R . .
H20F H 1.0287 0.4866 0.3232 0.085 Uiso 1 1 calc R . .
C21A C 0.81253(18) 0.56494(16) 0.32561(6) 0.0541(5) Uani 1 1 d . . .
H21D H 0.7600 0.6214 0.3251 0.081 Uiso 1 1 calc R . .
H21E H 0.8447 0.5567 0.3571 0.081 Uiso 1 1 calc R . .
H21F H 0.7683 0.5067 0.3168 0.081 Uiso 1 1 calc R . .

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
N1 0.0462(8) 0.0426(8) 0.0368(7) 0.0013(6) -0.0027(6) 0.0077(7)
N1A 0.0396(7) 0.0357(7) 0.0383(7) 0.0035(6) -0.0003(6) -0.0012(6)
O1 0.0869(11) 0.0541(8) 0.0625(9) 0.0141(7) -0.0234(8) -0.0203(8)
O2 0.0769(10) 0.0696(10) 0.0682(10) 0.0168(8) -0.0254(8) -0.0312(9)
O3 0.0471(7) 0.0443(7) 0.0522(7) 0.0055(6) 0.0033(6) 0.0098(6)
O4 0.0558(8) 0.0413(7) 0.0711(9) 0.0063(7) -0.0176(7) -0.0038(6)
O1A 0.0576(8) 0.0425(7) 0.0513(7) -0.0011(6) -0.0168(6) 0.0028(6)
O2A 0.0724(9) 0.0478(7) 0.0588(8) -0.0065(6) -0.0262(7) 0.0225(7)
O3A 0.0544(8) 0.0380(6) 0.0552(8) 0.0003(6) 0.0049(6) -0.0074(6)
O4A 0.0806(11) 0.0356(7) 0.0727(10) 0.0022(7) -0.0206(8) -0.0060(7)
C1 0.0530(11) 0.0446(10) 0.0572(11) 0.0045(9) -0.0100(9) -0.0122(9)
C2 0.0483(11) 0.0494(11) 0.0630(12) -0.0022(9) -0.0116(9) 0.0035(9)
C3 0.0445(10) 0.0416(10) 0.0576(11) 0.0023(8) -0.0073(8) -0.0040(8)
C4 0.0475(11) 0.0509(11) 0.0591(12) -0.0037(9) 0.0000(9) -0.0047(9)
C5 0.0449(10) 0.0538(11) 0.0456(10) -0.0096(9) -0.0014(8) 0.0030(9)
C6 0.0622(12) 0.0401(10) 0.0536(11) 0.0033(8) -0.0112(9) -0.0089(9)
C7 0.0605(14) 0.0825(17) 0.0949(18) 0.0311(14) -0.0081(13) 0.0017(13)
C8 0.0503(12) 0.0775(15) 0.0772(15) -0.0072(12) -0.0004(10) 0.0096(11)
C9 0.0753(16) 0.0608(14) 0.0953(18) -0.0249(13) -0.0264(13) 0.0027(13)
C10 0.0563(14) 0.0893(17) 0.0749(15) -0.0063(13) -0.0054(11) 0.0105(13)
C11 0.0384(9) 0.0394(9) 0.0348(8) 0.0034(7) 0.0017(7) -0.0015(7)
C12 0.0372(8) 0.0338(8) 0.0463(9) 0.0060(7) -0.0018(7) -0.0020(7)
C13 0.0469(10) 0.0430(10) 0.0472(10) 0.0015(8) -0.0129(8) 0.0076(8)
C14 0.0758(15) 0.0620(12) 0.0439(11) 0.0064(9) -0.0031(10) 0.0075(12)
C15 0.122(2) 0.099(2) 0.0484(13) 0.0101(14) 0.0045(15) 0.054(2)
C16 0.154(3) 0.113(3) 0.0687(18) -0.0397(19) -0.049(2) 0.072(3)
C17 0.111(3) 0.109(3) 0.111(3) -0.052(2) -0.063(2) 0.025(2)
C18 0.0661(15) 0.0660(14) 0.0921(17) -0.0159(13) -0.0301(13) 0.0010(12)
C19 0.0484(10) 0.0513(11) 0.0426(10) -0.0017(8) -0.0033(8) 0.0110(9)
C20 0.0910(16) 0.0453(11) 0.0632(13) -0.0077(10) -0.0260(12) 0.0031(11)
C21 0.0606(12) 0.0984(18) 0.0423(11) 0.0120(11) 0.0113(9) 0.0140(13)
C1A 0.0439(10) 0.0365(9) 0.0427(9) -0.0026(7) -0.0072(7) 0.0080(8)
C2A 0.0429(10) 0.0442(10) 0.0424(9) 0.0032(8) -0.0104(8) -0.0048(8)
C3A 0.0438(10) 0.0341(9) 0.0521(10) -0.0006(8) -0.0041(8) 0.0022(8)
C4A 0.0468(11) 0.0498(11) 0.0578(11) 0.0003(9) 0.0040(9) 0.0007(9)
C5A 0.0513(11) 0.0572(12) 0.0512(11) 0.0116(10) -0.0075(9) -0.0075(10)
C6A 0.0469(10) 0.0416(10) 0.0405(9) 0.0019(7) -0.0062(8) 0.0051(8)
C7A 0.0836(19) 0.102(2) 0.0886(19) -0.0371(16) -0.0266(15) -0.0004(17)
C8A 0.0535(13) 0.0958(19) 0.0968(18) 0.0183(15) -0.0118(13) -0.0217(14)
C9A 0.0731(14) 0.0587(13) 0.0627(13) 0.0165(10) -0.0258(11) -0.0096(11)
C10A 0.0540(13) 0.0941(17) 0.0495(12) -0.0097(11) -0.0021(9) -0.0138(12)
C11A 0.0419(9) 0.0336(8) 0.0363(8) 0.0017(7) -0.0011(7) 0.0031(7)
C12A 0.0398(9) 0.0371(9) 0.0424(9) -0.0036(7) 0.0030(7) 0.0017(7)
C13A 0.0476(10) 0.0398(9) 0.0425(9) -0.0053(7) 0.0003(8) -0.0070(8)
C14A 0.0566(12) 0.0732(14) 0.0499(11) -0.0071(10) 0.0066(9) -0.0072(11)
C15A 0.0816(17) 0.1043(19) 0.0415(11) 0.0004(12) 0.0049(11) -0.0209(16)
C16A 0.0931(19) 0.0863(18) 0.0496(12) 0.0135(12) -0.0196(13) -0.0223(15)
C17A 0.0706(15) 0.0813(16) 0.0642(14) 0.0107(12) -0.0186(12) 0.0050(13)
C18A 0.0566(12) 0.0672(13) 0.0481(11) 0.0044(9) -0.0039(9) 0.0067(11)
C19A 0.0666(12) 0.0444(10) 0.0420(10) 0.0068(8) -0.0044(9) -0.0122(10)
C20A 0.0573(12) 0.0536(12) 0.0584(12) 0.0088(10) -0.0079(10) 0.0152(10)
C21A 0.0529(11) 0.0660(13) 0.0435(10) 0.0080(9) 0.0076(8) -0.0078(10)

_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 C21 1.483(2) . ?
N1 C20 1.485(3) . ?
N1 C11 1.518(2) . ?
N1A C21A 1.486(2) . ?
N1A C20A 1.486(2) . ?
N1A C11A 1.517(2) . ?
O1 C6 1.263(2) . ?
O2 C6 1.244(2) . ?
O3 C12 1.427(2) . ?
O4 C19 1.403(2) . ?
O1A C6A 1.265(2) . ?
O2A C6A 1.250(2) . ?
O3A C12A 1.418(2) . ?
O4A C19A 1.407(2) . ?
C1 C6 1.499(3) . ?
C1 C2 1.509(3) . ?
C1 C3 1.517(3) . ?
C2 C3 1.496(3) . ?
C2 C10 1.500(3) . ?
C2 C9 1.511(3) . ?
C3 C4 1.481(3) . ?
C4 C5 1.311(3) . ?
C5 C7 1.486(3) . ?
C5 C8 1.505(3) . ?
C11 C19 1.521(2) . ?
C11 C12 1.528(2) . ?
C12 C13 1.513(2) . ?
C13 C14 1.382(3) . ?
C13 C18 1.384(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.371(5) . ?
C16 C17 1.356(5) . ?
C17 C18 1.380(4) . ?
C1A C6A 1.498(2) . ?
C1A C3A 1.503(2) . ?
C1A C2A 1.523(2) . ?
C2A C3A 1.504(2) . ?
C2A C10A 1.504(3) . ?
C2A C9A 1.505(3) . ?
C3A C4A 1.476(3) . ?
C4A C5A 1.313(3) . ?
C5A C7A 1.483(3) . ?
C5A C8A 1.497(3) . ?
C11A C19A 1.509(2) . ?
C11A C12A 1.533(2) . ?
C12A C13A 1.511(2) . ?
C13A C18A 1.377(3) . ?
C13A C14A 1.381(3) . ?
C14A C15A 1.399(3) . ?
C15A C16A 1.353(4) . ?
C16A C17A 1.370(4) . ?
C17A C18A 1.384(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
C21 N1 C20 110.81(17) . . ?
C21 N1 C11 116.06(15) . . ?
C20 N1 C11 112.03(14) . . ?
C21A N1A C20A 110.61(15) . . ?
C21A N1A C11A 113.57(14) . . ?
C20A N1A C11A 114.93(14) . . ?
C6 C1 C2 123.77(18) . . ?
C6 C1 C3 121.02(16) . . ?
C2 C1 C3 59.25(12) . . ?
C3 C2 C10 119.05(19) . . ?
C3 C2 C1 60.66(13) . . ?
C10 C2 C1 119.49(18) . . ?
C3 C2 C9 117.57(18) . . ?
C10 C2 C9 113.5(2) . . ?
C1 C2 C9 116.89(19) . . ?
C4 C3 C2 122.67(17) . . ?
C4 C3 C1 119.03(17) . . ?
C2 C3 C1 60.09(13) . . ?
C5 C4 C3 127.23(19) . . ?
C4 C5 C7 123.61(19) . . ?
C4 C5 C8 121.9(2) . . ?
C7 C5 C8 114.5(2) . . ?
O2 C6 O1 123.94(19) . . ?
O2 C6 C1 120.48(18) . . ?
O1 C6 C1 115.58(18) . . ?
N1 C11 C19 107.93(13) . . ?
N1 C11 C12 112.83(13) . . ?
C19 C11 C12 114.68(14) . . ?
O3 C12 C13 111.91(13) . . ?
O3 C12 C11 111.31(13) . . ?
C13 C12 C11 111.32(14) . . ?
C14 C13 C18 118.9(2) . . ?
C14 C13 C12 121.70(17) . . ?
C18 C13 C12 119.37(19) . . ?
C13 C14 C15 119.9(2) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C16 C15 119.8(3) . . ?
C16 C17 C18 120.6(3) . . ?
C17 C18 C13 120.2(3) . . ?
O4 C19 C11 112.35(15) . . ?
C6A C1A C3A 120.23(15) . . ?
C6A C1A C2A 122.27(16) . . ?
C3A C1A C2A 59.58(11) . . ?
C3A C2A C10A 118.18(17) . . ?
C3A C2A C9A 117.57(17) . . ?
C10A C2A C9A 114.28(18) . . ?
C3A C2A C1A 59.56(11) . . ?
C10A C2A C1A 119.52(16) . . ?
C9A C2A C1A 117.09(17) . . ?
C4A C3A C1A 121.68(16) . . ?
C4A C3A C2A 122.08(16) . . ?
C1A C3A C2A 60.86(11) . . ?
C5A C4A C3A 126.93(19) . . ?
C4A C5A C7A 122.8(2) . . ?
C4A C5A C8A 121.7(2) . . ?
C7A C5A C8A 115.5(2) . . ?
O2A C6A O1A 124.33(17) . . ?
O2A C6A C1A 118.56(16) . . ?
O1A C6A C1A 117.11(15) . . ?
C19A C11A N1A 108.03(14) . . ?
C19A C11A C12A 114.19(14) . . ?
N1A C11A C12A 112.52(13) . . ?
O3A C12A C13A 111.71(14) . . ?
O3A C12A C11A 107.52(13) . . ?
C13A C12A C11A 110.16(13) . . ?
C18A C13A C14A 118.62(18) . . ?
C18A C13A C12A 120.09(16) . . ?
C14A C13A C12A 121.28(18) . . ?
C13A C14A C15A 120.0(2) . . ?
C16A C15A C14A 120.3(2) . . ?
C15A C16A C17A 120.3(2) . . ?
C16A C17A C18A 119.8(2) . . ?
C13A C18A C17A 120.9(2) . . ?
O4A C19A C11A 109.75(16) . . ?

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 108.9(2) . . . . ?
C6 C1 C2 C10 0.1(3) . . . . ?
C3 C1 C2 C10 -108.8(2) . . . . ?
C6 C1 C2 C9 -143.0(2) . . . . ?
C3 C1 C2 C9 108.1(2) . . . . ?
C10 C2 C3 C4 -143.3(2) . . . . ?
C1 C2 C3 C4 107.2(2) . . . . ?
C9 C2 C3 C4 0.3(3) . . . . ?
C10 C2 C3 C1 109.5(2) . . . . ?
C9 C2 C3 C1 -107.0(2) . . . . ?
C6 C1 C3 C4 133.5(2) . . . . ?
C2 C1 C3 C4 -113.1(2) . . . . ?
C6 C1 C3 C2 -113.4(2) . . . . ?
C2 C3 C4 C5 120.8(2) . . . . ?
C1 C3 C4 C5 -168.00(19) . . . . ?
C3 C4 C5 C7 -3.0(3) . . . . ?
C3 C4 C5 C8 175.95(19) . . . . ?
C2 C1 C6 O2 -46.1(3) . . . . ?
C3 C1 C6 O2 25.5(3) . . . . ?
C2 C1 C6 O1 134.4(2) . . . . ?
C3 C1 C6 O1 -154.05(19) . . . . ?
C21 N1 C11 C19 -94.78(19) . . . . ?
C20 N1 C11 C19 136.57(17) . . . . ?
C21 N1 C11 C12 33.0(2) . . . . ?
C20 N1 C11 C12 -95.66(18) . . . . ?
N1 C11 C12 O3 53.89(18) . . . . ?
C19 C11 C12 O3 178.03(14) . . . . ?
N1 C11 C12 C13 179.49(14) . . . . ?
C19 C11 C12 C13 -56.37(19) . . . . ?
O3 C12 C13 C14 70.5(2) . . . . ?
C11 C12 C13 C14 -54.8(2) . . . . ?
O3 C12 C13 C18 -109.59(19) . . . . ?
C11 C12 C13 C18 125.15(19) . . . . ?
C18 C13 C14 C15 -1.0(3) . . . . ?
C12 C13 C14 C15 178.89(19) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C13 -0.1(5) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
C12 C13 C18 C17 -179.3(2) . . . . ?
N1 C11 C19 O4 55.49(19) . . . . ?
C12 C11 C19 O4 -71.21(19) . . . . ?
C6A C1A C2A C3A -108.65(18) . . . . ?
C6A C1A C2A C10A -1.4(3) . . . . ?
C3A C1A C2A C10A 107.3(2) . . . . ?
C6A C1A C2A C9A 143.76(18) . . . . ?
C3A C1A C2A C9A -107.60(19) . . . . ?
C6A C1A C3A C4A -136.27(19) . . . . ?
C2A C1A C3A C4A 111.7(2) . . . . ?
C6A C1A C3A C2A 111.99(19) . . . . ?
C10A C2A C3A C4A 139.41(19) . . . . ?
C9A C2A C3A C4A -4.3(3) . . . . ?
C1A C2A C3A C4A -111.1(2) . . . . ?
C10A C2A C3A C1A -109.48(18) . . . . ?
C9A C2A C3A C1A 106.81(19) . . . . ?
C1A C3A C4A C5A -176.63(19) . . . . ?
C2A C3A C4A C5A -103.4(2) . . . . ?
C3A C4A C5A C7A 0.8(4) . . . . ?
C3A C4A C5A C8A -178.1(2) . . . . ?
C3A C1A C6A O2A -8.7(3) . . . . ?
C2A C1A C6A O2A 62.3(2) . . . . ?
C3A C1A C6A O1A 171.71(16) . . . . ?
C2A C1A C6A O1A -117.26(19) . . . . ?
C21A N1A C11A C19A 141.75(16) . . . . ?
C20A N1A C11A C19A -89.47(18) . . . . ?
C21A N1A C11A C12A -91.27(17) . . . . ?
C20A N1A C11A C12A 37.5(2) . . . . ?
C19A C11A C12A O3A -177.74(14) . . . . ?
N1A C11A C12A O3A 58.64(17) . . . . ?
C19A C11A C12A C13A -55.79(19) . . . . ?
N1A C11A C12A C13A -179.41(13) . . . . ?
O3A C12A C13A C18A 49.9(2) . . . . ?
C11A C12A C13A C18A -69.5(2) . . . . ?
O3A C12A C13A C14A -131.59(18) . . . . ?
C11A C12A C13A C14A 108.99(19) . . . . ?
C18A C13A C14A C15A 0.8(3) . . . . ?
C12A C13A C14A C15A -177.7(2) . . . . ?
C13A C14A C15A C16A 0.3(4) . . . . ?
C14A C15A C16A C17A -0.8(4) . . . . ?
C15A C16A C17A C18A 0.2(4) . . . . ?
C14A C13A C18A C17A -1.4(3) . . . . ?
C12A C13A C18A C17A 177.2(2) . . . . ?
C16A C17A C18A C13A 0.9(4) . . . . ?
N1A C11A C19A O4A -65.76(18) . . . . ?
C12A C11A C19A O4A 168.24(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O2A 1.00(2) 1.68(2) 2.6383(19) 159.3(19) .
N1A HN1A O2 0.92(2) 1.90(2) 2.731(2) 150.0(18) 1_655
O3 HO3 O1A 0.89(2) 1.87(2) 2.7581(19) 171(2) 3_655
O4 HO4 O1A 0.86(3) 1.86(3) 2.7026(18) 166(3) .
O3A HO3A O1 0.86(2) 1.80(2) 2.6465(19) 168(2) 3_645
O4A HO4A O1 0.89(3) 1.70(3) 2.595(2) 178(3) 1_655

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.031


data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 287292'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'crisantemico-ammina senza SMe'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N O2, C10 H15 O2'
_chemical_formula_sum            'C21 H33 N O4'
_chemical_formula_weight         363.48

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

_cell_length_a                   7.3883(8)
_cell_length_b                   10.1582(11)
_cell_length_c                   28.935(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2171.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plates
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27500
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         29.98
_reflns_number_total             6299
_reflns_number_gt                4733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0537P)^2^+0.5421P] 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   -0.7(12)
_refine_ls_number_reflns         6299
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.7222(2) 0.80835(12) 0.97739(4) 0.0489(3) Uani 1 1 d . . .
O2 O 0.7513(3) 1.01582(12) 0.95634(5) 0.0602(4) Uani 1 1 d . . .
O3 O 0.3856(2) 0.62705(11) 0.94298(5) 0.0447(3) Uani 1 1 d . . .
HO3 H 0.331(3) 0.641(2) 0.9696(8) 0.041(5) Uiso 1 1 d . . .
O4 O 0.5982(3) 0.25266(15) 0.96262(8) 0.0815(6) Uani 1 1 d . . .
HO4 H 0.645(4) 0.174(3) 0.9610(10) 0.082(9) Uiso 1 1 d . . .
N1 N 0.7249(2) 0.54314(14) 0.96355(5) 0.0404(3) Uani 1 1 d . . .
HN1 H 0.681(4) 0.630(3) 0.9620(9) 0.072(8) Uiso 1 1 d . . .
C1 C 0.6622(3) 0.85800(17) 0.89995(6) 0.0440(4) Uani 1 1 d . . .
H1 H 0.5741 0.7860 0.8986 0.053 Uiso 1 1 calc R . .
C2 C 0.8016(4) 0.8559(2) 0.86193(8) 0.0586(6) Uani 1 1 d . . .
C3 C 0.6494(4) 0.9546(2) 0.86059(8) 0.0584(6) Uani 1 1 d . . .
H3 H 0.6844 1.0450 0.8683 0.070 Uiso 1 1 calc R . .
C4 C 0.5024(4) 0.9433(3) 0.82669(8) 0.0701(7) Uani 1 1 d . . .
H4 H 0.4319 0.8677 0.8287 0.084 Uiso 1 1 calc R . .
C5 C 0.4577(4) 1.0268(3) 0.79377(8) 0.0705(7) Uani 1 1 d . . .
C6 C 0.7141(3) 0.89900(16) 0.94779(6) 0.0404(4) Uani 1 1 d . . .
C7 C 0.5541(6) 1.1549(3) 0.78675(12) 0.1019(12) Uani 1 1 d . . .
H7A H 0.6675 1.1532 0.8029 0.153 Uiso 1 1 calc R . .
H7B H 0.4809 1.2255 0.7984 0.153 Uiso 1 1 calc R . .
H7C H 0.5757 1.1681 0.7544 0.153 Uiso 1 1 calc R . .
C8 C 0.3040(5) 1.0007(4) 0.76125(10) 0.0995(11) Uani 1 1 d . . .
H8A H 0.2148 1.0688 0.7643 0.149 Uiso 1 1 calc R . .
H8B H 0.2503 0.9171 0.7685 0.149 Uiso 1 1 calc R . .
H8C H 0.3485 0.9993 0.7301 0.149 Uiso 1 1 calc R . .
C9 C 0.7966(5) 0.7423(3) 0.82776(9) 0.0819(9) Uani 1 1 d . . .
H9A H 0.6746 0.7108 0.8248 0.123 Uiso 1 1 calc R . .
H9B H 0.8729 0.6724 0.8387 0.123 Uiso 1 1 calc R . .
H9C H 0.8391 0.7720 0.7982 0.123 Uiso 1 1 calc R . .
C10 C 0.9910(5) 0.9029(3) 0.87244(11) 0.0847(9) Uani 1 1 d . . .
H10A H 1.0576 0.8336 0.8873 0.127 Uiso 1 1 calc R . .
H10B H 0.9855 0.9780 0.8925 0.127 Uiso 1 1 calc R . .
H10C H 1.0505 0.9269 0.8442 0.127 Uiso 1 1 calc R . .
C11 C 0.6158(3) 0.46832(16) 0.92827(6) 0.0398(4) Uani 1 1 d . . .
H11 H 0.6435 0.5076 0.8982 0.048 Uiso 1 1 calc R . .
C12 C 0.4124(3) 0.48959(16) 0.93649(6) 0.0387(4) Uani 1 1 d . . .
H12 H 0.3746 0.4420 0.9643 0.046 Uiso 1 1 calc R . .
C13 C 0.3054(3) 0.44076(18) 0.89527(7) 0.0434(4) Uani 1 1 d . . .
C14 C 0.2802(4) 0.5190(3) 0.85696(8) 0.0635(6) Uani 1 1 d . . .
H14 H 0.3307 0.6028 0.8563 0.076 Uiso 1 1 calc R . .
C15 C 0.1813(5) 0.4750(4) 0.81955(10) 0.0885(9) Uani 1 1 d . . .
H15 H 0.1669 0.5289 0.7938 0.106 Uiso 1 1 calc R . .
C16 C 0.1042(5) 0.3524(4) 0.82015(13) 0.0941(10) Uani 1 1 d . . .
H16 H 0.0377 0.3226 0.7950 0.113 Uiso 1 1 calc R . .
C17 C 0.1258(5) 0.2761(3) 0.85746(13) 0.0921(10) Uani 1 1 d . . .
H17 H 0.0719 0.1933 0.8580 0.110 Uiso 1 1 calc R . .
C18 C 0.2267(4) 0.3172(2) 0.89547(10) 0.0675(6) Uani 1 1 d . . .
H18 H 0.2411 0.2620 0.9208 0.081 Uiso 1 1 calc R . .
C19 C 0.6674(3) 0.32301(19) 0.92492(9) 0.0575(6) Uani 1 1 d . . .
H19A H 0.6199 0.2864 0.8964 0.069 Uiso 1 1 calc R . .
H19B H 0.7981 0.3147 0.9243 0.069 Uiso 1 1 calc R . .
C20 C 0.9193(3) 0.5512(3) 0.95078(9) 0.0636(6) Uani 1 1 d . . .
H20A H 0.9758 0.4674 0.9559 0.095 Uiso 1 1 calc R . .
H20B H 0.9777 0.6168 0.9694 0.095 Uiso 1 1 calc R . .
H20C H 0.9300 0.5745 0.9188 0.095 Uiso 1 1 calc R . .
C21 C 0.7048(4) 0.5005(2) 1.01252(7) 0.0619(6) Uani 1 1 d . . .
H21A H 0.7658 0.5619 1.0324 0.093 Uiso 1 1 calc R . .
H21B H 0.7569 0.4146 1.0163 0.093 Uiso 1 1 calc R . .
H21C H 0.5787 0.4975 1.0205 0.093 Uiso 1 1 calc R . .

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
O1 0.0716(9) 0.0328(6) 0.0423(7) -0.0006(5) -0.0096(7) -0.0030(6)
O2 0.0856(11) 0.0255(5) 0.0696(9) -0.0072(6) -0.0174(8) 0.0062(7)
O3 0.0527(8) 0.0266(5) 0.0546(8) -0.0052(5) 0.0118(7) 0.0028(5)
O4 0.0968(14) 0.0301(7) 0.1176(16) 0.0091(8) 0.0314(12) 0.0162(8)
N1 0.0380(8) 0.0314(7) 0.0518(8) 0.0004(6) 0.0003(6) 0.0056(6)
C1 0.0584(12) 0.0312(8) 0.0423(9) 0.0014(7) -0.0066(8) -0.0020(8)
C2 0.0719(15) 0.0560(12) 0.0478(11) -0.0016(9) 0.0010(11) -0.0060(11)
C3 0.0832(16) 0.0379(9) 0.0540(12) 0.0078(9) -0.0076(11) -0.0068(11)
C4 0.0936(19) 0.0577(13) 0.0589(13) 0.0123(11) -0.0150(14) 0.0017(14)
C5 0.0939(19) 0.0717(16) 0.0458(11) 0.0134(11) 0.0011(12) 0.0242(14)
C6 0.0447(9) 0.0293(7) 0.0473(9) -0.0039(7) -0.0041(8) 0.0052(7)
C7 0.132(3) 0.081(2) 0.093(2) 0.0402(17) 0.005(2) 0.010(2)
C8 0.125(3) 0.112(3) 0.0613(16) 0.0135(16) -0.0221(17) 0.034(2)
C9 0.113(2) 0.0806(18) 0.0524(13) -0.0149(12) 0.0033(15) 0.0047(17)
C10 0.0766(19) 0.099(2) 0.0780(18) -0.0030(16) 0.0138(16) -0.0127(17)
C11 0.0454(10) 0.0289(7) 0.0450(9) -0.0027(7) 0.0070(8) 0.0024(7)
C12 0.0454(9) 0.0244(7) 0.0463(9) 0.0002(6) 0.0082(8) 0.0019(7)
C13 0.0388(9) 0.0390(9) 0.0523(10) -0.0073(8) 0.0085(8) -0.0002(8)
C14 0.0636(14) 0.0634(14) 0.0635(13) 0.0035(11) -0.0029(11) -0.0081(12)
C15 0.092(2) 0.110(3) 0.0628(15) -0.0001(16) -0.0153(15) -0.001(2)
C16 0.085(2) 0.108(3) 0.089(2) -0.039(2) -0.0166(18) -0.005(2)
C17 0.089(2) 0.0699(18) 0.117(3) -0.0322(19) -0.009(2) -0.0256(17)
C18 0.0770(16) 0.0442(11) 0.0813(16) -0.0103(11) -0.0032(14) -0.0130(12)
C19 0.0587(13) 0.0338(9) 0.0800(15) -0.0115(10) 0.0149(11) 0.0078(9)
C20 0.0424(11) 0.0671(14) 0.0814(16) -0.0077(13) -0.0003(11) -0.0004(10)
C21 0.0722(15) 0.0623(13) 0.0514(12) 0.0089(10) -0.0069(11) 0.0011(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
O1 C6 1.259(2) . ?
O2 C6 1.243(2) . ?
O3 C12 1.423(2) . ?
O4 C19 1.400(3) . ?
N1 C20 1.485(3) . ?
N1 C21 1.489(3) . ?
N1 C11 1.507(2) . ?
C1 C6 1.495(3) . ?
C1 C3 1.506(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.507(4) . ?
C2 C10 1.510(4) . ?
C2 C9 1.520(3) . ?
C3 C4 1.468(4) . ?
C4 C5 1.318(3) . ?
C5 C7 1.497(5) . ?
C5 C8 1.499(4) . ?
C11 C19 1.528(2) . ?
C11 C12 1.536(3) . ?
C12 C13 1.514(3) . ?
C13 C14 1.376(3) . ?
C13 C18 1.383(3) . ?
C14 C15 1.380(4) . ?
C15 C16 1.370(5) . ?
C16 C17 1.339(5) . ?
C17 C18 1.393(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
C20 N1 C21 110.42(18) . . ?
C20 N1 C11 112.14(16) . . ?
C21 N1 C11 116.40(16) . . ?
C6 C1 C3 122.33(16) . . ?
C6 C1 C2 120.31(19) . . ?
C3 C1 C2 60.01(16) . . ?
C3 C2 C1 59.97(15) . . ?
C3 C2 C10 119.1(2) . . ?
C1 C2 C10 118.8(2) . . ?
C3 C2 C9 118.1(2) . . ?
C1 C2 C9 118.0(2) . . ?
C10 C2 C9 113.2(3) . . ?
C4 C3 C1 120.1(2) . . ?
C4 C3 C2 121.2(2) . . ?
C1 C3 C2 60.02(15) . . ?
C5 C4 C3 128.2(3) . . ?
C4 C5 C7 122.6(3) . . ?
C4 C5 C8 122.0(3) . . ?
C7 C5 C8 115.4(2) . . ?
O2 C6 O1 123.53(17) . . ?
O2 C6 C1 120.45(17) . . ?
O1 C6 C1 115.99(15) . . ?
N1 C11 C19 113.38(17) . . ?
N1 C11 C12 110.34(13) . . ?
C19 C11 C12 112.94(15) . . ?
O3 C12 C13 110.67(15) . . ?
O3 C12 C11 107.12(14) . . ?
C13 C12 C11 110.03(14) . . ?
C14 C13 C18 118.0(2) . . ?
C14 C13 C12 121.05(18) . . ?
C18 C13 C12 120.9(2) . . ?
C13 C14 C15 121.1(2) . . ?
C16 C15 C14 120.3(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 C18 121.8(3) . . ?
C13 C18 C17 119.6(3) . . ?
O4 C19 C11 110.64(17) . . ?

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 -112.2(2) . . . . ?
C6 C1 C2 C10 -3.3(3) . . . . ?
C3 C1 C2 C10 108.9(3) . . . . ?
C6 C1 C2 C9 139.9(2) . . . . ?
C3 C1 C2 C9 -107.9(3) . . . . ?
C6 C1 C3 C4 -140.2(2) . . . . ?
C2 C1 C3 C4 110.9(3) . . . . ?
C6 C1 C3 C2 108.9(2) . . . . ?
C1 C2 C3 C4 -109.1(2) . . . . ?
C10 C2 C3 C4 142.5(2) . . . . ?
C9 C2 C3 C4 -1.3(3) . . . . ?
C10 C2 C3 C1 -108.4(2) . . . . ?
C9 C2 C3 C1 107.8(2) . . . . ?
C1 C3 C4 C5 171.1(3) . . . . ?
C2 C3 C4 C5 -117.8(3) . . . . ?
C3 C4 C5 C7 -1.8(5) . . . . ?
C3 C4 C5 C8 179.3(3) . . . . ?
C3 C1 C6 O2 -1.1(3) . . . . ?
C2 C1 C6 O2 70.5(3) . . . . ?
C3 C1 C6 O1 -179.05(19) . . . . ?
C2 C1 C6 O1 -107.4(2) . . . . ?
C20 N1 C11 C19 65.4(2) . . . . ?
C21 N1 C11 C19 -63.1(2) . . . . ?
C20 N1 C11 C12 -166.76(17) . . . . ?
C21 N1 C11 C12 64.7(2) . . . . ?
N1 C11 C12 O3 46.88(19) . . . . ?
C19 C11 C12 O3 174.94(17) . . . . ?
N1 C11 C12 C13 167.23(14) . . . . ?
C19 C11 C12 C13 -64.7(2) . . . . ?
O3 C12 C13 C14 34.5(3) . . . . ?
C11 C12 C13 C14 -83.7(2) . . . . ?
O3 C12 C13 C18 -144.1(2) . . . . ?
C11 C12 C13 C18 97.7(2) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 C15 -179.4(2) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C18 -0.9(6) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C12 C13 C18 C17 178.6(2) . . . . ?
C16 C17 C18 C13 0.9(5) . . . . ?
N1 C11 C19 O4 75.5(2) . . . . ?
C12 C11 C19 O4 -51.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O1 0.94(3) 1.89(3) 2.7238(19) 147(2) .
O3 HO3 O1 0.88(2) 1.81(2) 2.6827(19) 173(2) 4_467
O4 HO4 O2 0.87(3) 1.80(3) 2.665(2) 177(3) 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039