# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2005

data_global
_journal_name_full               'New J.Chem.(Nouv.J.Chim.)'

_journal_coden_Cambridge         0440

_publ_contact_author_name        'Prof K Harris'
_publ_contact_author_address     
;
Department of Chemistry
Cardiff University
P.O. Box 912
Cardiff
CF10 3TB
UK
;

_publ_contact_author_email       HARRISKDM@CARDIFF.AC.UK

_publ_section_title              
;
Hydrogen-bonded chains of a,w-diaminoalkane and
a,w-dihydroxyalkane guest molecules lead to disrupted tunnel structures
in urea inclusion compounds
;

_publ_section_references         
;
PLATON- (a) Spek, A. L. (1990) Acta Cryst. A46, C34.
(b) Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool,
Utrecht University, Utrecht, The Netherlands.

SHELXTL, program suite for structure solution and refinement,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA

SMART, program for instrument control and data aquisition,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA

SAINTPLUS, program suite for data processing,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA
;
loop_
_publ_author_name
'K. Harris'
'Benson M. Kariuki'
'Sang-Ok Lee'

data_s2pna21
_database_code_depnum_ccdc_archive 'CCDC 264610'
#associated with structure 1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '7(C1 H4 N2 O1), C7 H18 N2, C2 H6 O2'
_chemical_formula_sum            'C16 H52 N16 O9'
_chemical_formula_weight         612.74

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   Pna21

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

_cell_length_a                   14.7028(12)
_cell_length_b                   7.9159(7)
_cell_length_c                   28.661(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3335.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4415
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      70.96

_exptl_crystal_description       plate
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7308
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_process_details   'Sadabs in SaintPlus'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20168
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         70.96
_reflns_number_total             5684
_reflns_number_gt                4415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_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^)+(0.1261P)^2^+0.6329P] 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       0.0013(3)
_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   0.4(3)
_refine_ls_number_reflns         5684
_refine_ls_number_parameters     386
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1928
_refine_ls_wR_factor_gt          0.1702
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

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 0.5817(2) 0.5465(4) 1.8850(7) 0.0485(8) Uani 1 1 d . A 1
C2 C 0.4465(2) 0.4889(4) 1.7622(7) 0.0474(8) Uani 1 1 d . B 1
C3 C 0.4797(2) 0.3251(5) 2.0086(7) 0.0502(8) Uani 1 1 d . C 1
C4 C 0.4572(2) 0.6080(4) 2.1292(7) 0.0481(8) Uani 1 1 d . D 1
C5 C 0.2535(2) 0.9926(4) 2.0708(7) 0.0489(8) Uani 1 1 d . E 1
C6 C 0.3519(2) 1.1202(5) 2.1981(7) 0.0488(8) Uani 1 1 d . F 1
C7 C 0.1698(2) 0.4292(5) 1.8295(7) 0.0539(9) Uani 1 1 d . G 1
N1 N 0.6157(3) 0.6206(5) 1.8474(7) 0.0681(9) Uani 1 1 d . A 1
H1A H 0.6025 0.5828 1.8201 0.082 Uiso 1 1 calc R A 1
H1B H 0.6510 0.7066 1.8503 0.082 Uiso 1 1 calc R A 1
N2 N 0.6044(2) 0.6100(5) 1.9265(7) 0.0640(9) Uani 1 1 d . A 1
H2A H 0.5836 0.5648 1.9516 0.077 Uiso 1 1 calc R A 1
H2B H 0.6399 0.6961 1.9281 0.077 Uiso 1 1 calc R A 1
N3 N 0.3945(2) 0.5137(5) 1.7243(7) 0.0631(9) Uani 1 1 d . B 1
H3A H 0.4194 0.5222 1.6972 0.076 Uiso 1 1 calc R B 1
H3B H 0.3364 0.5212 1.7270 0.076 Uiso 1 1 calc R B 1
N4 N 0.4053(2) 0.4797(5) 1.8040(7) 0.0650(9) Uani 1 1 d . B 1
H4A H 0.4371 0.4659 1.8289 0.078 Uiso 1 1 calc R B 1
H4B H 0.3470 0.4875 1.8059 0.078 Uiso 1 1 calc R B 1
N5 N 0.4634(3) 0.2447(5) 1.9685(7) 0.0668(9) Uani 1 1 d . C 1
H5A H 0.4825 0.2867 1.9426 0.080 Uiso 1 1 calc R C 1
H5B H 0.4339 0.1509 1.9685 0.080 Uiso 1 1 calc R C 1
N6 N 0.4500(3) 0.2567(5) 2.0474(7) 0.0767(11) Uani 1 1 d . C 1
H6A H 0.4600 0.3058 2.0737 0.092 Uiso 1 1 calc R C 1
H6B H 0.4207 0.1627 2.0466 0.092 Uiso 1 1 calc R C 1
N7 N 0.4476(3) 0.6767(4) 2.0874(7) 0.0677(9) Uani 1 1 d . D 1
H7A H 0.4716 0.6291 2.0634 0.081 Uiso 1 1 calc R D 1
H7B H 0.4174 0.7690 2.0842 0.081 Uiso 1 1 calc R D 1
N8 N 0.4184(2) 0.6791(4) 2.1661(7) 0.0632(8) Uani 1 1 d . D 1
H8A H 0.4236 0.6328 2.1932 0.076 Uiso 1 1 calc R D 1
H8B H 0.3882 0.7714 2.1631 0.076 Uiso 1 1 calc R D 1
N9 N 0.2152(2) 1.0141(5) 2.0294(7) 0.0684(10) Uani 1 1 d . E 1
H9A H 0.2483 1.0160 2.0047 0.082 Uiso 1 1 calc R E 1
H9B H 0.1572 1.0262 2.0273 0.082 Uiso 1 1 calc R E 1
N10 N 0.1998(2) 0.9931(5) 2.1085(7) 0.0626(9) Uani 1 1 d . E 1
H10A H 0.2231 0.9810 2.1358 0.075 Uiso 1 1 calc R E 1
H10B H 0.1420 1.0054 2.1054 0.075 Uiso 1 1 calc R E 1
N11 N 0.3916(2) 1.1712(4) 2.1593(7) 0.0630(9) Uani 1 1 d . F 1
H11A H 0.3855 1.1135 2.1341 0.076 Uiso 1 1 calc R F 1
H11B H 0.4236 1.2622 2.1592 0.076 Uiso 1 1 calc R F 1
N12 N 0.3616(2) 1.2133(4) 2.2364(7) 0.0603(8) Uani 1 1 d . F 1
H12A H 0.3356 1.1829 2.2619 0.072 Uiso 1 1 calc R F 1
H12B H 0.3938 1.3039 2.2356 0.072 Uiso 1 1 calc R F 1
N13 N 0.1461(3) 0.3248(5) 1.7941(7) 0.0707(10) Uani 1 1 d . G 1
H13A H 0.1616 0.3489 1.7660 0.085 Uiso 1 1 calc R G 1
H13B H 0.1156 0.2345 1.7998 0.085 Uiso 1 1 calc R G 1
N14 N 0.1446(3) 0.3864(5) 1.8720(7) 0.0774(11) Uani 1 1 d . G 1
H14A H 0.1586 0.4497 1.8953 0.093 Uiso 1 1 calc R G 1
H14B H 0.1142 0.2950 1.8765 0.093 Uiso 1 1 calc R G 1
O1 O 0.52988(17) 0.4205(3) 1.8818(7) 0.0538(6) Uani 1 1 d . A 1
O2 O 0.53138(16) 0.4776(3) 1.7590(7) 0.0521(6) Uani 1 1 d . B 1
O3 O 0.5220(2) 0.4602(4) 2.0092(7) 0.0596(7) Uani 1 1 d . C 1
O4 O 0.50198(19) 0.4714(3) 2.1337(7) 0.0508(6) Uani 1 1 d . D 1
O5 O 0.33742(16) 0.9747(3) 2.0751(7) 0.0527(6) Uani 1 1 d . E 1
O6 O 0.30451(18) 0.9870(3) 2.1991(7) 0.0531(6) Uani 1 1 d . F 1
O7 O 0.21373(17) 0.5596(3) 1.8217(7) 0.0546(6) Uani 1 1 d . G 1
C8 C 0.3723(4) 0.7729(8) 1.9599(7) 0.0891(16) Uani 1 1 d . H 1
H8C H 0.3661 0.7483 1.9929 0.107 Uiso 1 1 calc R H 1
H8D H 0.4367 0.7705 1.9524 0.107 Uiso 1 1 calc R H 1
C9 C 0.3251(3) 0.6396(7) 1.9327(7) 0.0863(15) Uani 1 1 d . H 1
H9C H 0.3309 0.6655 1.8997 0.104 Uiso 1 1 calc R H 1
H9D H 0.3554 0.5326 1.9382 0.104 Uiso 1 1 calc R H 1
O8 O 0.3376(2) 0.9397(4) 1.9510(7) 0.0738(8) Uani 1 1 d . H 1
H8 H 0.3502 0.9675 1.9242 0.111 Uiso 1 1 calc R H 1
O9 O 0.2317(2) 0.6216(4) 1.9436(7) 0.0719(8) Uani 1 1 d . H 1
H9 H 0.2264 0.5747 1.9690 0.108 Uiso 1 1 calc R H 1
C10 C 0.3032(9) 1.0478(13) 1.5687(7) 0.188(5) Uani 1 1 d D I 1
H10C H 0.2403 1.0573 1.5785 0.226 Uiso 1 1 calc R I 1
H10D H 0.3259 1.1614 1.5637 0.226 Uiso 1 1 calc R I 1
C11 C 0.3569(7) 0.9682(11) 1.6079(7) 0.157(4) Uani 1 1 d D I 1
H11C H 0.4212 0.9910 1.6036 0.188 Uiso 1 1 calc R I 1
H11D H 0.3482 0.8468 1.6076 0.188 Uiso 1 1 calc R I 1
C12 C 0.3254(6) 1.0403(13) 1.6547(7) 0.165(4) Uani 1 1 d D I 1
H12C H 0.3293 1.1625 1.6535 0.197 Uiso 1 1 calc R I 1
H12D H 0.2620 1.0106 1.6594 0.197 Uiso 1 1 calc R I 1
C13 C 0.3795(5) 0.9784(11) 1.6953(7) 0.128(3) Uani 1 1 d D I 1
H13C H 0.4406 1.0237 1.6930 0.153 Uiso 1 1 calc R I 1
H13D H 0.3839 0.8564 1.6934 0.153 Uiso 1 1 calc R I 1
C14 C 0.3407(6) 1.0253(11) 1.7423(7) 0.162(4) Uani 1 1 d D I 1
H14C H 0.2840 0.9653 1.7471 0.194 Uiso 1 1 calc R I 1
H14D H 0.3277 1.1454 1.7429 0.194 Uiso 1 1 calc R I 1
C15 C 0.4061(5) 0.9824(12) 1.7815(7) 0.155(4) Uani 1 1 d D I 1
H15A H 0.4608 1.0501 1.7786 0.186 Uiso 1 1 calc R I 1
H15B H 0.4232 0.8642 1.7796 0.186 Uiso 1 1 calc R I 1
C16 C 0.3605(7) 1.0174(15) 1.8283(7) 0.156(5) Uani 0.644(11) 1 d PD I 1
H16A H 0.3423 1.1351 1.8298 0.187 Uiso 0.644(11) 1 calc PR I 1
H16B H 0.3062 0.9485 1.8311 0.187 Uiso 0.644(11) 1 calc PR I 1
N15 N 0.3055(10) 0.9600(11) 1.5251(7) 0.232(7) Uani 1 1 d D I 1
H15C H 0.2848 0.8553 1.5290 0.348 Uiso 1 1 calc R I 1
H15D H 0.3625 0.9562 1.5146 0.348 Uiso 1 1 calc R I 1
N16 N 0.4217(7) 0.9803(19) 1.8664(8) 0.175(5) Uani 0.644(11) 1 d PDU I 1
H16C H 0.4712 1.0443 1.8639 0.263 Uiso 0.644(11) 1 calc PR I 1
H16D H 0.4374 0.8718 1.8654 0.263 Uiso 0.644(11) 1 calc PR I 1
N16A N 0.3374(9) 1.0606(18) 1.8584(8) 0.093(4) Uani 0.356(11) 1 d PDU I 2
H16E H 0.3023 1.1366 1.8443 0.139 Uiso 0.356(11) 1 calc PR I 2
H16F H 0.3885 1.1099 1.8679 0.139 Uiso 0.356(11) 1 calc PR I 2
C16A C 0.3592(13) 0.9255(14) 1.8258(8) 0.156(5) Uani 0.356(11) 1 d PD I 2
H16I H 0.3029 0.8697 1.8171 0.187 Uiso 0.356(11) 1 calc PR I 2
H16J H 0.3964 0.8431 1.8420 0.187 Uiso 0.356(11) 1 calc PR I 2

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 0.0474(16) 0.0505(18) 0.0478(19) 0.0049(17) 0.0019(17) 0.0017(15)
C2 0.0460(17) 0.0501(18) 0.0461(19) 0.0023(16) -0.0007(16) 0.0000(15)
C3 0.0482(17) 0.056(2) 0.0467(17) 0.0042(18) 0.0020(16) -0.0074(16)
C4 0.0465(17) 0.0448(17) 0.053(2) -0.0021(17) -0.0043(16) -0.0006(14)
C5 0.050(2) 0.0474(17) 0.0490(18) -0.0048(17) 0.0016(17) 0.0005(14)
C6 0.0487(17) 0.0524(19) 0.0452(17) 0.0029(17) -0.0016(16) -0.0040(15)
C7 0.0483(17) 0.0517(19) 0.062(2) 0.0058(19) -0.0022(19) 0.0009(16)
N1 0.084(2) 0.074(2) 0.0468(18) 0.0056(17) 0.0035(17) -0.0253(18)
N2 0.070(2) 0.075(2) 0.0468(17) 0.0028(17) -0.0035(16) -0.0243(17)
N3 0.0519(17) 0.090(2) 0.0477(18) 0.0033(17) -0.0044(15) 0.0035(16)
N4 0.0480(17) 0.095(3) 0.0520(18) 0.0103(18) 0.0038(15) 0.0008(16)
N5 0.084(2) 0.063(2) 0.0536(18) -0.0006(17) 0.0020(17) -0.0186(18)
N6 0.106(3) 0.075(2) 0.0486(18) 0.0057(18) 0.004(2) -0.030(2)
N7 0.083(2) 0.0616(19) 0.059(2) 0.0076(17) -0.0071(18) 0.0176(17)
N8 0.0688(19) 0.0608(18) 0.060(2) -0.0052(17) 0.0010(17) 0.0123(16)
N9 0.0586(19) 0.096(3) 0.0504(18) -0.0048(18) -0.0052(16) 0.0063(17)
N10 0.0516(17) 0.083(2) 0.0536(19) -0.0048(17) 0.0078(15) -0.0039(15)
N11 0.074(2) 0.0650(19) 0.0502(18) -0.0017(16) 0.0073(17) -0.0203(16)
N12 0.077(2) 0.0559(17) 0.0479(18) -0.0064(15) 0.0044(16) -0.0146(16)
N13 0.082(2) 0.0566(18) 0.074(2) -0.0102(18) -0.0060(19) -0.0087(17)
N14 0.091(3) 0.076(2) 0.065(2) 0.0032(19) 0.009(2) -0.020(2)
O1 0.0618(14) 0.0550(13) 0.0445(12) 0.0054(12) -0.0022(12) -0.0119(12)
O2 0.0443(12) 0.0646(14) 0.0473(13) 0.0018(12) 0.0008(11) -0.0006(11)
O3 0.0683(16) 0.0673(17) 0.0432(13) 0.0035(13) 0.0004(13) -0.0189(13)
O4 0.0555(14) 0.0509(14) 0.0459(13) 0.0008(12) 0.0016(11) 0.0016(11)
O5 0.0501(14) 0.0592(13) 0.0487(13) -0.0012(12) -0.0006(12) 0.0005(10)
O6 0.0624(15) 0.0516(14) 0.0453(13) -0.0017(11) 0.0021(12) -0.0121(11)
O7 0.0550(13) 0.0542(14) 0.0545(15) -0.0008(12) 0.0016(12) -0.0041(11)
C8 0.069(3) 0.107(4) 0.091(4) -0.013(3) -0.016(3) 0.026(3)
C9 0.074(3) 0.088(3) 0.097(4) -0.022(3) -0.004(3) 0.027(2)
O8 0.0767(19) 0.085(2) 0.0593(18) -0.0084(17) 0.0052(16) -0.0056(17)
O9 0.0791(19) 0.0675(17) 0.0691(18) 0.0021(16) -0.0080(16) 0.0089(15)
C10 0.218(12) 0.164(8) 0.182(10) 0.001(8) -0.072(10) 0.047(9)
C11 0.228(11) 0.129(7) 0.113(6) 0.011(5) -0.031(7) 0.033(7)
C12 0.129(7) 0.157(8) 0.208(12) 0.041(8) -0.030(8) 0.028(6)
C13 0.126(6) 0.137(7) 0.119(6) 0.003(5) 0.019(5) 0.021(5)
C14 0.141(7) 0.102(5) 0.242(13) 0.002(7) 0.031(8) -0.004(5)
C15 0.112(6) 0.155(8) 0.197(10) -0.036(8) 0.047(7) -0.005(5)
C16 0.252(16) 0.081(8) 0.134(10) -0.026(8) 0.054(10) -0.030(10)
N15 0.45(2) 0.144(7) 0.102(5) 0.026(5) -0.045(8) 0.014(9)
N16 0.121(8) 0.207(12) 0.199(12) 0.026(10) 0.035(9) -0.022(8)
N16A 0.092(8) 0.119(10) 0.067(8) -0.003(7) 0.013(6) 0.031(7)
C16A 0.252(16) 0.081(8) 0.134(10) -0.026(8) 0.054(10) -0.030(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
C1 O1 1.258(4) . ?
C1 N1 1.326(5) . ?
C1 N2 1.333(5) . ?
C2 O2 1.255(4) . ?
C2 N3 1.344(5) . ?
C2 N4 1.345(5) . ?
C3 O3 1.237(4) . ?
C3 N6 1.314(5) . ?
C3 N5 1.335(5) . ?
C4 O4 1.273(4) . ?
C4 N7 1.324(5) . ?
C4 N8 1.327(5) . ?
C5 O5 1.248(4) . ?
C5 N9 1.323(5) . ?
C5 N10 1.339(5) . ?
C6 O6 1.264(4) . ?
C6 N11 1.320(5) . ?
C6 N12 1.330(5) . ?
C7 O7 1.237(5) . ?
C7 N14 1.318(5) . ?
C7 N13 1.353(5) . ?
C8 O8 1.439(7) . ?
C8 C9 1.485(8) . ?
C9 O9 1.415(6) . ?
C10 N15 1.430(9) . ?
C10 C11 1.512(8) . ?
C11 C12 1.528(8) . ?
C12 C13 1.493(8) . ?
C13 C14 1.509(8) . ?
C14 C15 1.516(8) . ?
C15 C16 1.526(8) . ?
C16 N16 1.446(9) . ?
N16A C16A 1.455(9) . ?

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
O1 C1 N1 121.4(4) . . ?
O1 C1 N2 121.0(3) . . ?
N1 C1 N2 117.6(3) . . ?
O2 C2 N3 121.0(4) . . ?
O2 C2 N4 120.7(4) . . ?
N3 C2 N4 118.2(3) . . ?
O3 C3 N6 120.7(4) . . ?
O3 C3 N5 121.0(3) . . ?
N6 C3 N5 118.3(3) . . ?
O4 C4 N7 119.8(3) . . ?
O4 C4 N8 120.1(3) . . ?
N7 C4 N8 120.2(3) . . ?
O5 C5 N9 121.6(4) . . ?
O5 C5 N10 120.2(4) . . ?
N9 C5 N10 118.1(3) . . ?
O6 C6 N11 121.2(4) . . ?
O6 C6 N12 120.1(3) . . ?
N11 C6 N12 118.6(3) . . ?
O7 C7 N14 121.8(4) . . ?
O7 C7 N13 120.6(4) . . ?
N14 C7 N13 117.6(4) . . ?
O8 C8 C9 113.1(4) . . ?
O9 C9 C8 114.2(4) . . ?
N15 C10 C11 115.8(8) . . ?
C10 C11 C12 109.8(7) . . ?
C13 C12 C11 113.6(7) . . ?
C12 C13 C14 114.5(7) . . ?
C13 C14 C15 111.5(7) . . ?
C14 C15 C16 109.3(7) . . ?
N16 C16 C15 110.7(8) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        70.96
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.049

#===END
# associated with structure 2
data_s1pna21
_database_code_depnum_ccdc_archive 'CCDC 264611'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '7(C1 H4 N2 O1), C8 H20 N2, C2 H6 O2'
_chemical_formula_sum            'C17 H54 N16 O9'
_chemical_formula_weight         626.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   14.5312(12)
_cell_length_b                   8.0457(7)
_cell_length_c                   28.962(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3386.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4238
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      70.55

_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_T_max  0.9064
_exptl_absorpt_process_details   'Sadabs in SaintPlus'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20612
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         70.55
_reflns_number_total             5622
_reflns_number_gt                4238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_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^)+(0.1053P)^2^+0.4957P] 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   0.0(3)
_refine_ls_number_reflns         5622
_refine_ls_number_parameters     383
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003

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 0.0507(2) 0.0058(4) 0.74415(13) 0.0497(8) Uani 1 1 d . . .
C2 C 0.9099(2) 0.9607(4) 0.62174(12) 0.0518(8) Uani 1 1 d . . .
C3 C 0.4585(2) 0.3881(4) 0.87757(12) 0.0509(8) Uani 1 1 d . . .
C4 C 0.2582(2) 0.0064(4) 0.93479(13) 0.0522(8) Uani 1 1 d . . .
C5 C 0.3554(2) 0.8761(4) 0.80846(12) 0.0513(8) Uani 1 1 d . . .
C6 C 0.8272(2) 1.4336(5) 0.67942(14) 0.0597(9) Uani 1 1 d . . .
C7 C 0.0184(2) 0.1623(5) 0.49860(12) 0.0525(8) Uani 1 1 d . . .
O1 O -0.03502(16) 0.0258(3) 0.74792(8) 0.0558(6) Uani 1 1 d . . .
O2 O 0.96273(17) 1.0831(3) 0.62519(8) 0.0577(6) Uani 1 1 d . . .
O3 O 0.50294(18) 0.5205(3) 0.87289(8) 0.0540(6) Uani 1 1 d . . .
O4 O 0.34455(16) 0.0170(3) 0.93030(8) 0.0539(6) Uani 1 1 d . . .
O5 O 0.30955(18) 1.0076(3) 0.80781(9) 0.0583(6) Uani 1 1 d . . .
O6 O 0.78506(16) 1.5640(3) 0.68701(9) 0.0583(6) Uani 1 1 d . . .
O7 O -0.02342(17) 0.0278(3) 0.49759(8) 0.0601(7) Uani 1 1 d . . .
N1 N 0.1033(2) -0.0186(4) 0.78097(11) 0.0646(9) Uani 1 1 d . . .
H1A H 0.0790 -0.0211 0.8080 0.078 Uiso 1 1 calc R . .
H1B H 0.1617 -0.0320 0.7778 0.078 Uiso 1 1 calc R . .
N2 N 0.0908(2) 0.0073(4) 0.70233(12) 0.0652(8) Uani 1 1 d . . .
H2A H 0.0580 0.0220 0.6780 0.078 Uiso 1 1 calc R . .
H2B H 0.1493 -0.0063 0.6999 0.078 Uiso 1 1 calc R . .
N3 N 0.8732(2) 0.8909(4) 0.65962(11) 0.0691(9) Uani 1 1 d . . .
H3A H 0.8860 0.9301 0.6865 0.083 Uiso 1 1 calc R . .
H3B H 0.8370 0.8069 0.6570 0.083 Uiso 1 1 calc R . .
N4 N 0.8886(2) 0.8937(5) 0.58136(11) 0.0688(9) Uani 1 1 d . . .
H4A H 0.9113 0.9341 0.5563 0.083 Uiso 1 1 calc R . .
H4B H 0.8521 0.8096 0.5802 0.083 Uiso 1 1 calc R . .
N5 N 0.4216(2) 0.3134(4) 0.84073(11) 0.0637(8) Uani 1 1 d . . .
H5A H 0.4283 0.3561 0.8137 0.076 Uiso 1 1 calc R . .
H5B H 0.3911 0.2225 0.8440 0.076 Uiso 1 1 calc R . .
N6 N 0.4473(2) 0.3191(4) 0.91863(11) 0.0662(8) Uani 1 1 d . . .
H6A H 0.4708 0.3651 0.9427 0.079 Uiso 1 1 calc R . .
H6B H 0.4166 0.2282 0.9213 0.079 Uiso 1 1 calc R . .
N7 N 0.2042(2) 0.0090(4) 0.89744(11) 0.0666(9) Uani 1 1 d . . .
H7A H 0.2282 0.0179 0.8704 0.080 Uiso 1 1 calc R . .
H7B H 0.1455 0.0018 0.9004 0.080 Uiso 1 1 calc R . .
N8 N 0.2197(2) -0.0083(5) 0.97603(12) 0.0738(10) Uani 1 1 d . . .
H8A H 0.2535 -0.0108 1.0004 0.089 Uiso 1 1 calc R . .
H8B H 0.1608 -0.0154 0.9784 0.089 Uiso 1 1 calc R . .
N9 N 0.3974(2) 0.8241(4) 0.84664(11) 0.0687(9) Uani 1 1 d . . .
H9A H 0.3934 0.8814 0.8716 0.082 Uiso 1 1 calc R . .
H9B H 0.4285 0.7333 0.8463 0.082 Uiso 1 1 calc R . .
N10 N 0.3653(2) 0.7859(4) 0.77011(11) 0.0658(9) Uani 1 1 d . . .
H10A H 0.3401 0.8182 0.7448 0.079 Uiso 1 1 calc R . .
H10B H 0.3969 0.6955 0.7707 0.079 Uiso 1 1 calc R . .
N11 N 0.8470(3) 1.3868(5) 0.63601(14) 0.0850(11) Uani 1 1 d . . .
H11A H 0.8302 1.4479 0.6131 0.102 Uiso 1 1 calc R . .
H11B H 0.8763 1.2957 0.6311 0.102 Uiso 1 1 calc R . .
N12 N 0.8527(2) 1.3331(5) 0.71364(13) 0.0755(10) Uani 1 1 d . . .
H12A H 0.8398 1.3585 0.7418 0.091 Uiso 1 1 calc R . .
H12B H 0.8820 1.2428 0.7076 0.091 Uiso 1 1 calc R . .
N13 N 0.0521(3) 0.2258(5) 0.45901(12) 0.0764(10) Uani 1 1 d . . .
H13A H 0.0446 0.1733 0.4334 0.092 Uiso 1 1 calc R . .
H13B H 0.0812 0.3189 0.4593 0.092 Uiso 1 1 calc R . .
N14 N 0.0335(2) 0.2446(5) 0.53699(12) 0.0725(9) Uani 1 1 d . . .
H14A H 0.0141 0.2057 0.5629 0.087 Uiso 1 1 calc R . .
H14B H 0.0627 0.3375 0.5363 0.087 Uiso 1 1 calc R . .
C8 C 0.6154(3) 0.7920(6) 0.55033(18) 0.0837(13) Uani 1 1 d . . .
H8C H 0.6173 0.7573 0.5183 0.100 Uiso 1 1 calc R . .
H8D H 0.5512 0.7983 0.5594 0.100 Uiso 1 1 calc R . .
C9 C 0.6623(3) 0.6618(6) 0.57933(17) 0.0810(13) Uani 1 1 d . . .
H9C H 0.6583 0.6947 0.6115 0.097 Uiso 1 1 calc R . .
H9D H 0.6290 0.5579 0.5760 0.097 Uiso 1 1 calc R . .
O8 O 0.6544(2) 0.9520(4) 0.55380(10) 0.0760(8) Uani 1 1 d . . .
H8 H 0.6591 0.9779 0.5811 0.114 Uiso 1 1 calc R . .
O9 O 0.7550(2) 0.6340(4) 0.56831(11) 0.0765(8) Uani 1 1 d . . .
H9 H 0.7584 0.5837 0.5437 0.115 Uiso 1 1 calc R . .
C10 C 0.6548(6) 1.0277(11) 0.9635(3) 0.133(2) Uani 1 1 d D . .
H10C H 0.6607 1.1465 0.9587 0.159 Uiso 1 1 calc R . .
H10D H 0.6013 1.0086 0.9828 0.159 Uiso 1 1 calc R . .
C11 C 0.6412(14) 0.9428(17) 0.9176(4) 0.281(9) Uani 1 1 d D . .
H11C H 0.6697 0.8338 0.9187 0.337 Uiso 1 1 calc R . .
H11D H 0.5759 0.9270 0.9124 0.337 Uiso 1 1 calc R . .
C12 C 0.6792(9) 1.0341(14) 0.8796(3) 0.206(6) Uani 1 1 d D . .
H12C H 0.7456 1.0401 0.8828 0.248 Uiso 1 1 calc R . .
H12D H 0.6552 1.1466 0.8798 0.248 Uiso 1 1 calc R . .
C13 C 0.6547(9) 0.9498(13) 0.8339(3) 0.177(4) Uani 1 1 d D . .
H13C H 0.6951 0.8558 0.8284 0.212 Uiso 1 1 calc R . .
H13D H 0.5917 0.9100 0.8347 0.212 Uiso 1 1 calc R . .
C14 C 0.6657(12) 1.0712(16) 0.7982(3) 0.260(9) Uani 1 1 d D . .
H14C H 0.7217 1.1338 0.8035 0.312 Uiso 1 1 calc R . .
H14D H 0.6144 1.1482 0.7990 0.312 Uiso 1 1 calc R . .
C15 C 0.6702(9) 0.9864(15) 0.7501(3) 0.201(5) Uani 1 1 d D . .
H15A H 0.7251 1.0230 0.7340 0.242 Uiso 1 1 calc R . .
H15B H 0.6741 0.8668 0.7540 0.242 Uiso 1 1 calc R . .
C16 C 0.5934(7) 1.0252(14) 0.7242(3) 0.169(4) Uani 1 1 d D . .
H16A H 0.5846 1.1447 0.7254 0.203 Uiso 1 1 calc R . .
H16B H 0.5403 0.9742 0.7387 0.203 Uiso 1 1 calc R . .
C17 C 0.5952(6) 0.9733(11) 0.6744(2) 0.134(3) Uani 1 1 d D . .
H17A H 0.6183 0.8602 0.6731 0.161 Uiso 1 1 calc R . .
H17B H 0.5322 0.9708 0.6634 0.161 Uiso 1 1 calc R . .
N15 N 0.7340(6) 0.9677(10) 0.9861(3) 0.181(4) Uani 1 1 d D . .
H15C H 0.7832 0.9859 0.9686 0.271 Uiso 1 1 calc R . .
H15D H 0.7280 0.8591 0.9912 0.271 Uiso 1 1 calc R . .
N16 N 0.6480(5) 1.0710(8) 0.64252(19) 0.140(2) Uani 1 1 d D . .
H16C H 0.7007 1.1013 0.6557 0.210 Uiso 1 1 calc R . .
H16D H 0.6161 1.1612 0.6347 0.210 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
C1 0.0479(19) 0.0474(18) 0.054(2) -0.0007(15) 0.0021(14) -0.0010(14)
C2 0.0485(17) 0.058(2) 0.048(2) 0.0031(16) 0.0039(15) 0.0016(15)
C3 0.0464(18) 0.0492(18) 0.057(2) -0.0008(16) 0.0019(15) 0.0036(15)
C4 0.0521(19) 0.0523(19) 0.0522(19) -0.0044(15) -0.0024(15) -0.0018(15)
C5 0.0529(19) 0.054(2) 0.0466(19) 0.0012(15) -0.0006(14) 0.0041(16)
C6 0.0491(18) 0.060(2) 0.070(3) -0.0041(19) -0.0054(17) -0.0036(17)
C7 0.0499(17) 0.061(2) 0.0469(19) 0.0046(16) -0.0002(14) -0.0067(16)
O1 0.0458(13) 0.0682(15) 0.0535(14) 0.0024(12) 0.0006(11) -0.0033(11)
O2 0.0626(15) 0.0613(15) 0.0490(14) 0.0028(12) -0.0008(11) -0.0109(12)
O3 0.0545(13) 0.0561(15) 0.0513(14) 0.0000(11) -0.0024(10) -0.0065(11)
O4 0.0479(13) 0.0609(14) 0.0528(14) -0.0011(11) 0.0006(10) -0.0002(10)
O5 0.0678(16) 0.0579(15) 0.0492(14) -0.0040(11) -0.0020(11) 0.0132(12)
O6 0.0573(13) 0.0587(14) 0.0590(15) -0.0017(11) 0.0028(11) 0.0041(12)
O7 0.0642(15) 0.0711(17) 0.0449(14) 0.0029(12) 0.0050(11) -0.0144(12)
N1 0.0469(16) 0.092(2) 0.0555(19) 0.0028(16) -0.0048(13) 0.0056(15)
N2 0.0526(17) 0.089(2) 0.0536(18) 0.0055(16) 0.0079(13) 0.0017(16)
N3 0.083(2) 0.078(2) 0.0461(18) 0.0052(16) 0.0062(15) -0.0245(18)
N4 0.070(2) 0.089(2) 0.0474(18) 0.0009(16) 0.0008(14) -0.0239(18)
N5 0.0655(18) 0.0650(19) 0.0605(19) -0.0046(16) -0.0048(14) -0.0141(15)
N6 0.078(2) 0.0638(19) 0.0563(19) 0.0067(15) -0.0011(16) -0.0107(15)
N7 0.0490(17) 0.095(3) 0.0562(19) -0.0028(16) -0.0083(14) 0.0048(16)
N8 0.0573(18) 0.109(3) 0.055(2) -0.0057(17) 0.0026(15) -0.0009(19)
N9 0.079(2) 0.074(2) 0.0536(19) -0.0024(16) -0.0130(16) 0.0241(17)
N10 0.087(2) 0.0615(19) 0.0489(19) -0.0041(14) -0.0035(15) 0.0178(17)
N11 0.102(3) 0.082(3) 0.071(3) -0.0125(19) 0.009(2) 0.019(2)
N12 0.079(2) 0.061(2) 0.087(3) 0.0041(18) -0.0111(18) 0.0081(17)
N13 0.104(3) 0.073(2) 0.0520(19) 0.0052(16) 0.0095(18) -0.029(2)
N14 0.092(2) 0.072(2) 0.0536(19) -0.0007(16) 0.0043(16) -0.0245(19)
C8 0.072(3) 0.090(3) 0.089(3) 0.006(3) -0.015(2) -0.014(2)
C9 0.086(3) 0.075(3) 0.082(3) 0.001(2) 0.013(2) -0.019(2)
O8 0.088(2) 0.081(2) 0.0590(18) 0.0073(14) -0.0008(15) -0.0027(16)
O9 0.0823(19) 0.078(2) 0.0690(19) -0.0052(15) -0.0023(14) -0.0113(15)
C10 0.151(7) 0.145(6) 0.101(5) -0.014(4) -0.015(5) 0.001(5)
C11 0.43(3) 0.184(12) 0.232(17) -0.067(12) -0.041(18) -0.056(14)
C12 0.284(14) 0.166(9) 0.170(10) -0.059(8) 0.104(10) -0.083(9)
C13 0.206(10) 0.166(9) 0.159(9) -0.047(8) 0.014(7) -0.017(8)
C14 0.43(3) 0.203(14) 0.148(10) -0.008(10) -0.102(13) 0.002(15)
C15 0.257(14) 0.219(11) 0.128(8) -0.027(7) -0.047(9) 0.059(10)
C16 0.174(8) 0.226(11) 0.106(6) -0.031(6) 0.008(6) 0.039(8)
C17 0.141(6) 0.170(7) 0.092(5) -0.002(4) 0.005(4) 0.026(5)
N15 0.178(7) 0.199(7) 0.165(7) -0.088(6) -0.036(6) 0.054(6)
N16 0.205(7) 0.128(5) 0.087(4) -0.011(3) 0.006(4) -0.017(5)

_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 O1 1.261(4) . ?
C1 N1 1.327(5) . ?
C1 N2 1.344(5) . ?
C2 O2 1.253(4) . ?
C2 N4 1.325(5) . ?
C2 N3 1.343(5) . ?
C3 O3 1.254(4) . ?
C3 N6 1.323(5) . ?
C3 N5 1.337(5) . ?
C4 O4 1.264(4) . ?
C4 N8 1.324(5) . ?
C4 N7 1.337(5) . ?
C5 O5 1.250(4) . ?
C5 N9 1.330(5) . ?
C5 N10 1.334(5) . ?
C6 O6 1.234(5) . ?
C6 N12 1.332(5) . ?
C6 N11 1.343(5) . ?
C7 O7 1.241(4) . ?
C7 N14 1.313(5) . ?
C7 N13 1.348(5) . ?
C8 O8 1.410(6) . ?
C8 C9 1.506(7) . ?
C9 O9 1.403(6) . ?
C10 N15 1.410(8) . ?
C10 C11 1.507(9) . ?
C11 C12 1.435(9) . ?
C12 C13 1.529(9) . ?
C13 C14 1.431(9) . ?
C14 C15 1.553(9) . ?
C15 C16 1.381(8) . ?
C16 C17 1.502(8) . ?
C17 N16 1.435(7) . ?

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
O1 C1 N1 121.2(3) . . ?
O1 C1 N2 120.3(3) . . ?
N1 C1 N2 118.4(3) . . ?
O2 C2 N4 122.3(3) . . ?
O2 C2 N3 120.5(3) . . ?
N4 C2 N3 117.3(3) . . ?
O3 C3 N6 121.2(3) . . ?
O3 C3 N5 120.2(3) . . ?
N6 C3 N5 118.6(3) . . ?
O4 C4 N8 121.3(3) . . ?
O4 C4 N7 119.9(3) . . ?
N8 C4 N7 118.9(3) . . ?
O5 C5 N9 121.5(3) . . ?
O5 C5 N10 120.3(3) . . ?
N9 C5 N10 118.1(3) . . ?
O6 C6 N12 121.4(4) . . ?
O6 C6 N11 120.7(4) . . ?
N12 C6 N11 117.8(4) . . ?
O7 C7 N14 122.8(3) . . ?
O7 C7 N13 119.3(3) . . ?
N14 C7 N13 117.9(3) . . ?
O8 C8 C9 114.4(4) . . ?
O9 C9 C8 114.8(4) . . ?
N15 C10 C11 111.2(10) . . ?
C12 C11 C10 113.2(9) . . ?
C11 C12 C13 110.3(9) . . ?
C14 C13 C12 107.2(8) . . ?
C13 C14 C15 110.7(10) . . ?
C16 C15 C14 110.7(9) . . ?
C15 C16 C17 116.4(8) . . ?
N16 C17 C16 118.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        70.55
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.048
#===END

data_soleer3
_database_code_depnum_ccdc_archive 'CCDC 264612'
#associated with structure 3
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '8(C1 H4 N2 O1), C8 H20 N2, C3 H8 O2'
_chemical_formula_sum            'C19 H60 N18 O10'
_chemical_formula_weight         700.85

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           Trigonal
_symmetry_space_group_name_H-M   P3121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   8.2121(2)
_cell_length_b                   8.2121(2)
_cell_length_c                   48.6159(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2839.34(13)
_cell_formula_units_Z            3
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3102
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      70.46

_exptl_crystal_description       Plate
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_process_details   'Sadabs in SaintPlus'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18182
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         70.46
_reflns_number_total             3552
_reflns_number_gt                3102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_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^)+(0.1336P)^2^+1.1596P] 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   0.4(5)
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     243
_refine_ls_number_restraints     401
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2160
_refine_ls_wR_factor_gt          0.2056
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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 0.8050(4) 0.7354(4) 0.60820(6) 0.0415(6) Uani 1 1 d U . .
C2 C 1.4049(4) 0.9234(4) 0.64940(6) 0.0402(6) Uani 1 1 d U . .
C3 C 0.4830(4) 0.1592(4) 0.79687(5) 0.0418(6) Uani 1 1 d U . .
C4 C 0.6157(4) 0.7402(4) 0.76005(6) 0.0417(6) Uani 1 1 d U . .
C5 C 1.0780(7) 1.1791(7) 0.83590(12) 0.0965(15) Uani 1 1 d U . .
H5C H 1.1362 1.1786 0.8532 0.116 Uiso 1 1 calc R . .
H5D H 1.1598 1.1846 0.8211 0.116 Uiso 1 1 calc R . .
C6 C 0.8876(10) 1.0000 0.8333 0.105(2) Uani 1 2 d SU . .
H6C H 0.8125 0.9893 0.8494 0.126 Uiso 0.50 1 calc PR . .
H6D H 0.8232 1.0107 0.8173 0.126 Uiso 0.50 1 calc PR . .
N1 N 0.8892(4) 0.7616(4) 0.58365(5) 0.0570(7) Uani 1 1 d U . .
H1A H 0.8225 0.7194 0.5690 0.068 Uiso 1 1 calc R . .
H1B H 1.0099 0.8207 0.5826 0.068 Uiso 1 1 calc R . .
N2 N 0.9095(4) 0.8030(4) 0.63062(5) 0.0536(7) Uani 1 1 d U . .
H2A H 0.8568 0.7880 0.6464 0.064 Uiso 1 1 calc R . .
H2B H 1.0302 0.8619 0.6294 0.064 Uiso 1 1 calc R . .
N3 N 1.4794(4) 0.9012(4) 0.67243(5) 0.0519(6) Uani 1 1 d U . .
H3A H 1.4658 0.9461 0.6877 0.062 Uiso 1 1 calc R . .
H3B H 1.5410 0.8420 0.6720 0.062 Uiso 1 1 calc R . .
N4 N 1.4283(4) 0.8514(4) 0.62629(5) 0.0536(7) Uani 1 1 d U . .
H4A H 1.3811 0.8633 0.6111 0.064 Uiso 1 1 calc R . .
H4B H 1.4906 0.7927 0.6265 0.064 Uiso 1 1 calc R . .
N5 N 0.5330(5) 0.2603(4) 0.77369(5) 0.0601(8) Uani 1 1 d U . .
H5A H 0.4961 0.2050 0.7580 0.072 Uiso 1 1 calc R . .
H5B H 0.6021 0.3807 0.7744 0.072 Uiso 1 1 calc R . .
N6 N 0.5434(4) 0.2505(4) 0.82061(5) 0.0538(7) Uani 1 1 d U . .
H6A H 0.5135 0.1890 0.8358 0.065 Uiso 1 1 calc R . .
H6B H 0.6123 0.3710 0.8207 0.065 Uiso 1 1 calc R . .
N7 N 0.5901(4) 0.8227(4) 0.73844(5) 0.0573(7) Uani 1 1 d U . .
H7A H 0.6344 0.8169 0.7227 0.069 Uiso 1 1 calc R . .
H7B H 0.5292 0.8821 0.7402 0.069 Uiso 1 1 calc R . .
N8 N 0.5445(4) 0.7497(4) 0.78413(5) 0.0580(7) Uani 1 1 d U . .
H8A H 0.5590 0.6958 0.7983 0.070 Uiso 1 1 calc R . .
H8B H 0.4839 0.8096 0.7855 0.070 Uiso 1 1 calc R . .
O1 O 0.6271(3) 0.6483(3) 0.60985(4) 0.0437(5) Uani 1 1 d U . .
O2 O 1.3141(3) 1.0096(3) 0.64948(4) 0.0444(5) Uani 1 1 d U . .
O3 O 0.3820(3) -0.0168(3) 0.79590(3) 0.0478(5) Uani 1 1 d U . .
O4 O 0.7052(3) 0.6528(3) 0.75753(4) 0.0462(5) Uani 1 1 d U . .
O5 O 1.0550(4) 1.3366(4) 0.83466(5) 0.0748(8) Uani 1 1 d U . .
H5 H 1.0750 1.3782 0.8189 0.112 Uiso 1 1 calc R . .
C7 C 1.043(3) 1.331(2) 0.75634(13) 0.116(3) Uani 0.559(7) 1 d PDU A 1
H7C H 0.9336 1.2052 0.7563 0.139 Uiso 0.559(7) 1 calc PR A 1
H7D H 1.1546 1.3199 0.7578 0.139 Uiso 0.559(7) 1 calc PR A 1
C8 C 1.049(2) 1.4344(12) 0.72963(15) 0.142(4) Uani 0.559(7) 1 d PDU A 1
H8C H 0.9638 1.4841 0.7311 0.170 Uiso 0.559(7) 1 calc PR A 1
H8D H 1.1747 1.5390 0.7267 0.170 Uiso 0.559(7) 1 calc PR A 1
C9 C 0.9902(19) 1.2981(12) 0.70509(13) 0.153(4) Uani 0.559(7) 1 d PDU A 1
H9A H 1.0373 1.2118 0.7076 0.183 Uiso 0.559(7) 1 calc PR A 1
H9B H 0.8542 1.2252 0.7039 0.183 Uiso 0.559(7) 1 calc PR A 1
C10 C 1.0718(8) 1.4123(14) 0.67851(10) 0.204(6) Uani 0.559(7) 1 d PDU . 1
H10A H 1.1118 1.5432 0.6821 0.245 Uiso 0.559(7) 1 calc PR A 1
H10B H 1.1816 1.4050 0.6730 0.245 Uiso 0.559(7) 1 calc PR A 1
N9 N 1.0322(12) 1.4387(10) 0.77971(12) 0.089(2) Uani 0.559(7) 1 d PDU A 1
H9C H 0.9352 1.4574 0.7774 0.133 Uiso 0.559(7) 1 calc PR A 1
H9D H 1.1380 1.5491 0.7807 0.133 Uiso 0.559(7) 1 calc PR A 1
C7A C 1.008(3) 1.359(3) 0.75594(9) 0.116(3) Uani 0.441(7) 1 d PDU A 2
H7A1 H 1.0370 1.4888 0.7564 0.139 Uiso 0.441(7) 1 calc PR A 2
H7A2 H 0.8723 1.2787 0.7566 0.139 Uiso 0.441(7) 1 calc PR A 2
C8A C 1.085(2) 1.322(2) 0.72931(7) 0.151(6) Uani 0.441(7) 1 d PDU A 2
H8A1 H 1.2204 1.4050 0.7283 0.181 Uiso 0.441(7) 1 calc PR A 2
H8A2 H 1.0603 1.1928 0.7291 0.181 Uiso 0.441(7) 1 calc PR A 2
C9A C 0.989(2) 1.356(2) 0.70459(10) 0.153(4) Uani 0.441(7) 1 d PDU A 2
H9A1 H 0.8551 1.2670 0.7050 0.183 Uiso 0.441(7) 1 calc PR A 2
H9A2 H 1.0077 1.4819 0.7054 0.183 Uiso 0.441(7) 1 calc PR A 2
C10A C 1.0758(5) 1.3307(16) 0.67796(6) 0.204(6) Uani 0.441(7) 1 d PDU . 2
H10C H 1.1815 1.4504 0.6723 0.245 Uiso 0.441(7) 1 calc PR A 2
H10D H 1.1208 1.2432 0.6810 0.245 Uiso 0.441(7) 1 calc PR A 2
N9A N 1.094(3) 1.320(3) 0.77968(7) 0.244(10) Uani 0.441(7) 1 d PDU A 2
H9A3 H 1.2181 1.3803 0.7777 0.366 Uiso 0.441(7) 1 calc PR A 2
H9A4 H 1.0509 1.1966 0.7807 0.366 Uiso 0.441(7) 1 calc PR A 2

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 0.0429(14) 0.0410(14) 0.0429(15) 0.0031(11) -0.0005(11) 0.0229(13)
C2 0.0398(14) 0.0385(14) 0.0438(15) 0.0027(11) 0.0045(11) 0.0206(11)
C3 0.0461(15) 0.0421(14) 0.0377(15) 0.0015(11) 0.0034(11) 0.0224(13)
C4 0.0387(14) 0.0378(15) 0.0451(15) -0.0007(11) -0.0015(12) 0.0165(12)
C5 0.079(3) 0.094(3) 0.113(4) -0.026(3) -0.011(3) 0.041(3)
C6 0.087(4) 0.067(4) 0.155(7) -0.037(4) -0.018(2) 0.0336(19)
N1 0.0413(13) 0.0774(19) 0.0446(14) -0.0006(13) 0.0030(10) 0.0239(14)
N2 0.0454(14) 0.0631(16) 0.0448(14) -0.0039(12) -0.0064(10) 0.0215(13)
N3 0.0640(17) 0.0686(17) 0.0409(13) -0.0036(12) -0.0032(12) 0.0465(14)
N4 0.0738(19) 0.0670(17) 0.0391(13) -0.0058(11) -0.0041(12) 0.0495(16)
N5 0.084(2) 0.0433(14) 0.0357(13) 0.0076(10) 0.0021(13) 0.0188(14)
N6 0.0677(17) 0.0422(13) 0.0386(13) 0.0004(10) -0.0024(12) 0.0177(13)
N7 0.0696(18) 0.0629(17) 0.0532(15) 0.0096(13) -0.0001(13) 0.0435(15)
N8 0.0764(19) 0.0643(17) 0.0470(14) 0.0013(12) 0.0063(13) 0.0455(16)
O1 0.0426(10) 0.0491(11) 0.0372(10) 0.0008(8) -0.0001(8) 0.0212(9)
O2 0.0535(12) 0.0490(11) 0.0385(10) -0.0029(8) -0.0022(8) 0.0315(9)
O3 0.0667(14) 0.0378(11) 0.0348(10) 0.0040(8) 0.0022(8) 0.0231(10)
O4 0.0522(12) 0.0475(11) 0.0425(11) 0.0041(9) 0.0028(9) 0.0276(9)
O5 0.0822(18) 0.0599(15) 0.0664(16) -0.0018(13) 0.0056(14) 0.0237(14)
C7 0.121(7) 0.110(6) 0.149(6) 0.015(5) 0.024(5) 0.082(5)
C8 0.121(8) 0.074(6) 0.207(12) 0.012(7) -0.007(8) 0.032(6)
C9 0.110(5) 0.075(7) 0.306(11) 0.041(7) 0.009(6) 0.071(6)
C10 0.186(10) 0.075(7) 0.354(15) 0.019(9) 0.113(9) 0.068(7)
N9 0.128(6) 0.086(4) 0.067(4) 0.012(3) 0.005(4) 0.065(5)
C7A 0.121(7) 0.110(6) 0.149(6) 0.015(5) 0.024(5) 0.082(5)
C8A 0.107(9) 0.147(11) 0.218(13) -0.048(10) 0.049(9) 0.078(8)
C9A 0.110(5) 0.075(7) 0.306(11) 0.041(7) 0.009(6) 0.071(6)
C10A 0.186(10) 0.075(7) 0.354(15) 0.019(9) 0.113(9) 0.068(7)
N9A 0.27(2) 0.26(2) 0.220(19) 0.026(18) 0.055(18) 0.150(18)

_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 O1 1.268(3) . ?
C1 N2 1.325(4) . ?
C1 N1 1.342(4) . ?
C2 O2 1.259(3) . ?
C2 N4 1.328(4) . ?
C2 N3 1.331(4) . ?
C3 O3 1.257(4) . ?
C3 N6 1.330(4) . ?
C3 N5 1.337(4) . ?
C4 O4 1.265(3) . ?
C4 N7 1.322(4) . ?
C4 N8 1.328(4) . ?
C5 O5 1.398(6) . ?
C5 C6 1.524(7) . ?
C6 C5 1.524(7) 4_676 ?
C7 N9 1.4695(10) . ?
C7 C8 1.5403(10) . ?
C8 C9 1.5397(10) . ?
C9 C10 1.5394(11) . ?
C10 C10 1.5392(10) 5_766 ?
C7A N9A 1.4698(10) . ?
C7A C8A 1.5400(10) . ?
C8A C9A 1.5399(10) . ?
C9A C10A 1.5398(10) . ?
C10A C10A 1.5394(10) 5_766 ?

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
O1 C1 N2 120.4(3) . . ?
O1 C1 N1 120.2(3) . . ?
N2 C1 N1 119.4(3) . . ?
O2 C2 N4 120.8(3) . . ?
O2 C2 N3 121.1(3) . . ?
N4 C2 N3 118.2(3) . . ?
O3 C3 N6 121.8(2) . . ?
O3 C3 N5 120.3(3) . . ?
N6 C3 N5 118.0(3) . . ?
O4 C4 N7 120.0(3) . . ?
O4 C4 N8 121.1(3) . . ?
N7 C4 N8 118.9(3) . . ?
O5 C5 C6 110.0(5) . . ?
C5 C6 C5 114.2(7) 4_676 . ?
N9 C7 C8 108.3(6) . . ?
C9 C8 C7 109.8(5) . . ?
C10 C9 C8 109.0(5) . . ?
C10 C10 C9 112.2(6) 5_766 . ?
N9A C7A C8A 108.95(10) . . ?
C9A C8A C7A 108.56(10) . . ?
C10A C9A C8A 108.54(10) . . ?
C10A C10A C9A 108.62(10) 5_766 . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        70.46
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.062
#===END

data_soleer4
_database_code_depnum_ccdc_archive 'CCDC 264613'
# associated with structure 4
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C1 H4 N2 O1), C4 H10 O2'
_chemical_formula_sum            'C6 H18 N4 O4'
_chemical_formula_weight         210.24

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   5.2046(3)
_cell_length_b                   7.3638(4)
_cell_length_c                   14.6064(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.604(3)
_cell_angle_gamma                90.00
_cell_volume                     553.50(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      6.13
_cell_measurement_theta_max      70.30

_exptl_crystal_description       needle
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'Sadabs in SaintPlus'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3392
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.13
_diffrn_reflns_theta_max         70.30
_reflns_number_total             1005
_reflns_number_gt                930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_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^)+(0.0473P)^2^+0.0681P] 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       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1005
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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 -0.4488(2) -0.09249(14) 0.13971(7) 0.0387(3) Uani 1 1 d . . .
C2 C -0.1814(3) 0.41400(18) 0.09749(9) 0.0548(4) Uani 1 1 d . . .
H2A H -0.2270 0.5314 0.1206 0.066 Uiso 1 1 calc R . .
H2B H -0.3326 0.3678 0.0573 0.066 Uiso 1 1 calc R . .
C3 C 0.0372(2) 0.43860(16) 0.04163(9) 0.0489(3) Uani 1 1 d . . .
H3A H 0.0878 0.3208 0.0206 0.059 Uiso 1 1 calc R . .
H3B H 0.1861 0.4900 0.0810 0.059 Uiso 1 1 calc R . .
N1 N -0.4240(2) -0.16295(16) 0.22421(7) 0.0560(3) Uani 1 1 d . . .
H1A H -0.2719 -0.1817 0.2548 0.067 Uiso 1 1 calc R . .
H1B H -0.5600 -0.1898 0.2484 0.067 Uiso 1 1 calc R . .
N2 N -0.68824(18) -0.06488(15) 0.09451(7) 0.0555(4) Uani 1 1 d . . .
H2C H -0.7095 -0.0191 0.0397 0.067 Uiso 1 1 calc R . .
H2D H -0.8212 -0.0929 0.1202 0.067 Uiso 1 1 calc R . .
O1 O -0.25225(14) -0.05218(11) 0.10305(5) 0.0458(3) Uani 1 1 d . . .
O2 O -0.11806(17) 0.29237(12) 0.17425(6) 0.0520(3) Uani 1 1 d . . .
H2 H -0.1252 0.1873 0.1554 0.078 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
C1 0.0346(6) 0.0402(6) 0.0432(6) -0.0053(4) 0.0126(4) -0.0006(4)
C2 0.0491(8) 0.0588(7) 0.0599(8) 0.0019(6) 0.0202(6) 0.0057(5)
C3 0.0405(6) 0.0535(7) 0.0547(7) -0.0014(5) 0.0132(5) 0.0001(5)
N1 0.0429(6) 0.0812(8) 0.0465(6) 0.0103(5) 0.0156(4) 0.0006(5)
N2 0.0311(6) 0.0821(8) 0.0550(6) 0.0098(5) 0.0116(4) -0.0004(5)
O1 0.0308(5) 0.0612(5) 0.0472(5) 0.0040(3) 0.0121(3) -0.0016(3)
O2 0.0521(5) 0.0569(5) 0.0496(5) -0.0037(4) 0.0157(4) -0.0059(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
C1 O1 1.2588(12) . ?
C1 N1 1.3273(15) . ?
C1 N2 1.3359(15) . ?
C2 O2 1.4344(15) . ?
C2 C3 1.5069(16) . ?
C3 C3 1.519(2) 3_565 ?

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
O1 C1 N1 121.04(10) . . ?
O1 C1 N2 120.75(10) . . ?
N1 C1 N2 118.21(10) . . ?
O2 C2 C3 113.22(10) . . ?
C2 C3 C3 112.50(13) . 3_565 ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        70.30
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
#===END