data_global
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182

loop_
_publ_author_name
'Thomas C. W. Mak'
'Xiao-Ming Chen'
'Mei-Fun Cheng'
'Chi-Keung Lam'
'Chi-Lun Li'
'Wai-Kee Li'
'Jie-Peng Zhang'

_publ_contact_author_name        'Prof Thomas C. W. Mak'
_publ_contact_author_address     
;
Chemistry
The Chinese University of Hong Kong
Shatin, New Territories
Hong Kong SAR
852
CHINA
;

_publ_contact_author_email       TCWMAK@CUHK.EDU.HK

_publ_section_title              
;
Stabilization of D5h and C2v valence tautomers of
the croconate dianion
;

data_compound(1)
_database_code_depnum_ccdc_archive 'CCDC 210097'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis(tetra-n-propylammonium) croconate-urea-water (1/3/8)
;
_chemical_name_common            
'bis(tetra-n-propylammonium) croconate-urea-water (1/3/8)'
_chemical_melting_point          ' 88-91 deg. (dec) '
_chemical_formula_moiety         '   [(n-C3H7)4N+]2(C5O5 )2-. 3(NH2)2CO. 8H2O '
_chemical_formula_sum            'C32 H84 N8 O16'
_chemical_formula_weight         837.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   33.3992(17)
_cell_length_b                   16.2615(8)
_cell_length_c                   17.7104(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2100(10)
_cell_angle_gamma                90.00
_cell_volume                     9324.6(8)
_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       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3680
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_correction_T_min  0.898080
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123K
_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 APEX CCD diffractometer '
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41285
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         28.02
_reflns_number_total             11221
_reflns_number_gt                9545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'SMART for Windows NT, Bruker AXS Inc., Madison, Wisconsin, USA, 1998.'
_computing_cell_refinement       
;SAINT-PLUS for Windows NT, Ver. 6.0, Bruker AXS Inc., Madison,
Wisconsin, USA, 1997.
;
_computing_data_reduction        
;SAINT-PLUS for Windows NT, Ver. 6.0, Bruker AXS Inc.,
Madison, Wisconsin, USA, 1997.
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;XP-Interactive Molecular Graphics, Ver. 5.1, Bruker AXS Inc., Madison,
Wisconsin, USA, 1998.
;
_computing_publication_material  
'SHELXTL-Bruker AXS Inc., Madison, Wisconsin, USA, 1998.'

_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^)+(0.0696P)^2^+4.5655P] 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_number_reflns         11221
_refine_ls_number_parameters     570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1189
_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 0.38389(2) 0.35628(5) 0.06015(5) 0.02983(19) Uani 1 1 d . . .
C1 C 0.41471(3) 0.32936(6) 0.04063(6) 0.0215(2) Uani 1 1 d . . .
O2 O 0.39487(2) 0.35513(5) -0.09698(5) 0.03079(19) Uani 1 1 d . . .
C2 C 0.42015(3) 0.32731(7) -0.03920(6) 0.0220(2) Uani 1 1 d . . .
O3 O 0.47476(3) 0.27264(5) -0.09444(5) 0.02889(18) Uani 1 1 d . . .
C3 C 0.45994(3) 0.28723(6) -0.03783(6) 0.0220(2) Uani 1 1 d . . .
O4 O 0.51343(3) 0.23293(6) 0.06848(5) 0.0348(2) Uani 1 1 d . . .
C4 C 0.47938(3) 0.26743(7) 0.04362(6) 0.0229(2) Uani 1 1 d . . .
O5 O 0.45989(3) 0.28854(5) 0.16425(5) 0.02991(19) Uani 1 1 d . . .
C5 C 0.45210(3) 0.29453(6) 0.09245(6) 0.0217(2) Uani 1 1 d . . .
O6 O 0.25664(2) 0.49856(5) -0.10684(5) 0.02642(17) Uani 1 1 d . . .
C6 C 0.28968(3) 0.46021(6) -0.08092(6) 0.0218(2) Uani 1 1 d . . .
N1 N 0.30136(3) 0.43579(7) -0.00654(6) 0.0319(2) Uani 1 1 d . . .
H6A H 0.2860 0.4464 0.0248 0.038 Uiso 1 1 calc R . .
H6B H 0.3242 0.4095 0.0099 0.038 Uiso 1 1 calc R . .
N2 N 0.31465(3) 0.43980(6) -0.12714(6) 0.0258(2) Uani 1 1 d . . .
H5A H 0.3080 0.4531 -0.1756 0.031 Uiso 1 1 calc R . .
H5B H 0.3372 0.4135 -0.1082 0.031 Uiso 1 1 calc R . .
O7 O 0.62235(2) 0.13651(5) -0.05580(5) 0.03043(19) Uani 1 1 d . . .
C7 C 0.58845(3) 0.16038(7) -0.04589(7) 0.0238(2) Uani 1 1 d . . .
N3 N 0.55840(3) 0.19058(6) -0.10493(6) 0.0275(2) Uani 1 1 d . . .
H1A H 0.5623 0.1938 -0.1511 0.033 Uiso 1 1 calc R . .
H1B H 0.5354 0.2066 -0.0964 0.033 Uiso 1 1 calc R . .
N4 N 0.57915(3) 0.15482(7) 0.02319(6) 0.0360(3) Uani 1 1 d . . .
H2A H 0.5967 0.1343 0.0625 0.043 Uiso 1 1 calc R . .
H2B H 0.5556 0.1717 0.0283 0.043 Uiso 1 1 calc R . .
O8 O 0.24723(2) 0.48432(5) 0.09521(5) 0.02629(17) Uani 1 1 d . . .
C8 C 0.21594(3) 0.52749(7) 0.06903(7) 0.0230(2) Uani 1 1 d . . .
N5 N 0.20389(3) 0.54826(7) -0.00608(6) 0.0335(2) Uani 1 1 d . . .
H4A H 0.2178 0.5319 -0.0381 0.040 Uiso 1 1 calc R . .
H4B H 0.1822 0.5780 -0.0224 0.040 Uiso 1 1 calc R . .
N6 N 0.19301(3) 0.55674(6) 0.11631(6) 0.0296(2) Uani 1 1 d . . .
H3A H 0.1999 0.5457 0.1653 0.035 Uiso 1 1 calc R . .
H3B H 0.1716 0.5864 0.0974 0.035 Uiso 1 1 calc R . .
O1W O 0.31857(3) 0.49530(6) -0.28606(5) 0.03031(19) Uani 1 1 d . . .
H1WA H 0.2973(6) 0.4995(10) -0.3227(11) 0.044(5) Uiso 1 1 d . . .
H1WB H 0.3335(6) 0.5369(12) -0.2895(11) 0.051(5) Uiso 1 1 d . . .
O2W O 0.18430(3) 0.47891(6) -0.22379(5) 0.02943(19) Uani 1 1 d . . .
H2WA H 0.2052(6) 0.4811(10) -0.1909(11) 0.043(5) Uiso 1 1 d . . .
H2WB H 0.1699(5) 0.5170(11) -0.2159(10) 0.041(4) Uiso 1 1 d . . .
O3W O 0.42359(3) 0.23079(6) -0.24033(6) 0.0349(2) Uani 1 1 d . . .
H3WA H 0.4398(6) 0.2418(11) -0.1945(11) 0.045(5) Uiso 1 1 d . . .
H3WB H 0.4096(5) 0.2685(10) -0.2431(9) 0.026(4) Uiso 1 1 d . . .
O4W O 0.42868(3) 0.25238(6) 0.28898(6) 0.02905(18) Uani 1 1 d . . .
H4WA H 0.4384(5) 0.2636(10) 0.2522(11) 0.041(4) Uiso 1 1 d . . .
H4WB H 0.4482(6) 0.2516(10) 0.3298(11) 0.043(4) Uiso 1 1 d . . .
O5W O 0.37404(3) 0.36548(7) -0.25320(6) 0.0424(2) Uani 1 1 d . . .
H5WA H 0.3816(6) 0.3669(12) -0.1912(12) 0.064(6) Uiso 1 1 d . . .
H5WB H 0.3516(7) 0.4127(15) -0.2714(14) 0.091(7) Uiso 1 1 d . . .
O6W O 0.37198(3) 0.37571(6) 0.20918(6) 0.0359(2) Uani 1 1 d . . .
H6WA H 0.3771(5) 0.3650(9) 0.1658(10) 0.033(4) Uiso 1 1 d . . .
H6WB H 0.3866(6) 0.3453(11) 0.2403(11) 0.048(5) Uiso 1 1 d . . .
O7W O 0.63252(3) 0.10403(6) -0.20236(6) 0.0323(2) Uani 1 1 d . . .
H7WA H 0.6182(5) 0.1369(11) -0.2305(10) 0.042(5) Uiso 1 1 d . . .
H7WB H 0.6301(5) 0.1147(11) -0.1564(11) 0.044(4) Uiso 1 1 d . . .
O8W O 0.62503(3) 0.12652(6) 0.18687(5) 0.0337(2) Uani 1 1 d . . .
H8WA H 0.6124(5) 0.1607(11) 0.2056(10) 0.037(4) Uiso 1 1 d . . .
H8WB H 0.6412(6) 0.1019(11) 0.2257(11) 0.051(5) Uiso 1 1 d . . .
N7 N 0.25211(2) 0.77275(5) 0.24832(5) 0.01841(18) Uani 1 1 d . . .
C9 C 0.28542(3) 0.82946(6) 0.29412(6) 0.0210(2) Uani 1 1 d . . .
H9A H 0.2959 0.8624 0.2576 0.025 Uiso 1 1 calc R . .
H9B H 0.2729 0.8667 0.3245 0.025 Uiso 1 1 calc R . .
C10 C 0.32152(3) 0.78668(7) 0.34868(7) 0.0272(2) Uani 1 1 d . . .
H10A H 0.3369 0.7552 0.3187 0.033 Uiso 1 1 calc R . .
H10B H 0.3114 0.7490 0.3823 0.033 Uiso 1 1 calc R . .
C11 C 0.34954(4) 0.85046(8) 0.39771(8) 0.0329(3) Uani 1 1 d . . .
H11A H 0.3723 0.8234 0.4324 0.049 Uiso 1 1 calc R . .
H11B H 0.3342 0.8813 0.4274 0.049 Uiso 1 1 calc R . .
H11C H 0.3598 0.8871 0.3643 0.049 Uiso 1 1 calc R . .
C12 C 0.23483(3) 0.71833(6) 0.30271(6) 0.0209(2) Uani 1 1 d . . .
H12A H 0.2119 0.6869 0.2717 0.025 Uiso 1 1 calc R . .
H12B H 0.2561 0.6795 0.3275 0.025 Uiso 1 1 calc R . .
C13 C 0.21993(4) 0.76327(8) 0.36579(7) 0.0305(3) Uani 1 1 d . . .
H13A H 0.1981 0.8013 0.3421 0.037 Uiso 1 1 calc R . .
H13B H 0.2425 0.7947 0.3978 0.037 Uiso 1 1 calc R . .
C14 C 0.20388(4) 0.70215(9) 0.41623(8) 0.0371(3) Uani 1 1 d . . .
H14A H 0.1946 0.7312 0.4560 0.056 Uiso 1 1 calc R . .
H14B H 0.2256 0.6649 0.4401 0.056 Uiso 1 1 calc R . .
H14C H 0.1813 0.6717 0.3845 0.056 Uiso 1 1 calc R . .
C15 C 0.21853(3) 0.82773(7) 0.20040(6) 0.0222(2) Uani 1 1 d . . .
H15A H 0.2064 0.8591 0.2357 0.027 Uiso 1 1 calc R . .
H15B H 0.2312 0.8665 0.1717 0.027 Uiso 1 1 calc R . .
C16 C 0.18430(4) 0.78320(8) 0.14329(8) 0.0328(3) Uani 1 1 d . . .
H16A H 0.1705 0.7456 0.1711 0.039 Uiso 1 1 calc R . .
H16B H 0.1958 0.7514 0.1074 0.039 Uiso 1 1 calc R . .
C17 C 0.15340(4) 0.84502(8) 0.09835(8) 0.0359(3) Uani 1 1 d . . .
H17A H 0.1318 0.8165 0.0621 0.054 Uiso 1 1 calc R . .
H17B H 0.1671 0.8818 0.0705 0.054 Uiso 1 1 calc R . .
H17C H 0.1418 0.8759 0.1340 0.054 Uiso 1 1 calc R . .
C18 C 0.26939(3) 0.71566(6) 0.19596(6) 0.0211(2) Uani 1 1 d . . .
H18A H 0.2915 0.6833 0.2283 0.025 Uiso 1 1 calc R . .
H18B H 0.2478 0.6779 0.1707 0.025 Uiso 1 1 calc R . .
C19 C 0.28596(4) 0.75833(8) 0.13371(7) 0.0317(3) Uani 1 1 d . . .
H19A H 0.3102 0.7902 0.1581 0.038 Uiso 1 1 calc R . .
H19B H 0.2652 0.7958 0.1045 0.038 Uiso 1 1 calc R . .
C20 C 0.29710(4) 0.69568(9) 0.07869(7) 0.0364(3) Uani 1 1 d . . .
H20A H 0.3074 0.7236 0.0396 0.055 Uiso 1 1 calc R . .
H20B H 0.2730 0.6646 0.0542 0.055 Uiso 1 1 calc R . .
H20C H 0.3179 0.6592 0.1075 0.055 Uiso 1 1 calc R . .
N8 N 0.5000 0.52032(7) 0.2500 0.0189(2) Uani 1 2 d S . .
C21 C 0.47971(3) 0.46432(7) 0.29854(6) 0.0221(2) Uani 1 1 d . . .
H21A H 0.4587 0.4319 0.2635 0.027 Uiso 1 1 calc R . .
H21B H 0.5004 0.4266 0.3273 0.027 Uiso 1 1 calc R . .
C22 C 0.46000(5) 0.50786(9) 0.35553(9) 0.0420(3) Uani 1 1 d . . .
H22A H 0.4791 0.5484 0.3842 0.050 Uiso 1 1 calc R . .
H22B H 0.4355 0.5366 0.3271 0.050 Uiso 1 1 calc R . .
C23 C 0.44847(5) 0.44901(9) 0.41170(9) 0.0429(3) Uani 1 1 d . . .
H23A H 0.4363 0.4787 0.4472 0.064 Uiso 1 1 calc R . .
H23B H 0.4727 0.4209 0.4403 0.064 Uiso 1 1 calc R . .
H23C H 0.4290 0.4097 0.3836 0.064 Uiso 1 1 calc R . .
C24 C 0.46807(3) 0.57586(7) 0.19840(6) 0.0227(2) Uani 1 1 d . . .
H24A H 0.4547 0.6080 0.2313 0.027 Uiso 1 1 calc R . .
H24B H 0.4823 0.6139 0.1717 0.027 Uiso 1 1 calc R . .
C25 C 0.43516(4) 0.53147(8) 0.13815(8) 0.0343(3) Uani 1 1 d . . .
H25A H 0.4188 0.4974 0.1641 0.041 Uiso 1 1 calc R . .
H25B H 0.4481 0.4960 0.1071 0.041 Uiso 1 1 calc R . .
C26 C 0.40735(4) 0.59286(9) 0.08559(8) 0.0388(3) Uani 1 1 d . . .
H26A H 0.3867 0.5639 0.0476 0.058 Uiso 1 1 calc R . .
H26B H 0.4236 0.6262 0.0596 0.058 Uiso 1 1 calc R . .
H26C H 0.3941 0.6273 0.1163 0.058 Uiso 1 1 calc R . .
N9 N 0.0000 0.52347(7) 0.2500 0.0189(2) Uani 1 2 d S . .
C27 C 0.01698(3) 0.46730(6) 0.19670(6) 0.0215(2) Uani 1 1 d . . .
H27A H 0.0389 0.4343 0.2286 0.026 Uiso 1 1 calc R . .
H27B H -0.0048 0.4300 0.1711 0.026 Uiso 1 1 calc R . .
C28 C 0.03373(4) 0.50987(8) 0.13456(7) 0.0306(3) Uani 1 1 d . . .
H28A H 0.0585 0.5406 0.1588 0.037 Uiso 1 1 calc R . .
H28B H 0.0134 0.5482 0.1057 0.037 Uiso 1 1 calc R . .
C29 C 0.04374(4) 0.44572(9) 0.07956(8) 0.0375(3) Uani 1 1 d . . .
H29A H 0.0545 0.4724 0.0404 0.056 Uiso 1 1 calc R . .
H29B H 0.0191 0.4161 0.0552 0.056 Uiso 1 1 calc R . .
H29C H 0.0640 0.4081 0.1084 0.056 Uiso 1 1 calc R . .
C30 C 0.03341(3) 0.57969(7) 0.29649(6) 0.0220(2) Uani 1 1 d . . .
H30A H 0.0447 0.6116 0.2603 0.026 Uiso 1 1 calc R . .
H30B H 0.0208 0.6180 0.3257 0.026 Uiso 1 1 calc R . .
C31 C 0.06859(4) 0.53645(8) 0.35267(8) 0.0326(3) Uani 1 1 d . . .
H31A H 0.0578 0.5040 0.3892 0.039 Uiso 1 1 calc R . .
H31B H 0.0823 0.4995 0.3241 0.039 Uiso 1 1 calc R . .
C32 C 0.09927(4) 0.59854(9) 0.39667(8) 0.0395(3) Uani 1 1 d . . .
H32A H 0.1214 0.5703 0.4321 0.059 Uiso 1 1 calc R . .
H32B H 0.0857 0.6346 0.4254 0.059 Uiso 1 1 calc R . .
H32C H 0.1102 0.6301 0.3605 0.059 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 0.0231(4) 0.0376(5) 0.0287(4) -0.0012(3) 0.0063(3) 0.0059(3)
C1 0.0193(5) 0.0200(5) 0.0237(5) -0.0014(4) 0.0027(4) -0.0018(4)
O2 0.0242(4) 0.0396(5) 0.0255(4) 0.0082(3) 0.0002(3) 0.0025(3)
C2 0.0187(5) 0.0216(5) 0.0238(5) 0.0008(4) 0.0018(4) -0.0031(4)
O3 0.0280(4) 0.0366(5) 0.0226(4) -0.0018(3) 0.0072(3) 0.0014(3)
C3 0.0211(5) 0.0221(5) 0.0217(5) -0.0010(4) 0.0027(4) -0.0025(4)
O4 0.0264(4) 0.0499(5) 0.0258(4) -0.0015(4) 0.0019(3) 0.0146(4)
C4 0.0207(5) 0.0251(5) 0.0211(5) -0.0021(4) 0.0018(4) 0.0007(4)
O5 0.0303(4) 0.0385(5) 0.0198(4) -0.0006(3) 0.0039(3) 0.0004(3)
C5 0.0208(5) 0.0209(5) 0.0221(5) -0.0015(4) 0.0028(4) -0.0023(4)
O6 0.0214(4) 0.0314(4) 0.0258(4) 0.0035(3) 0.0046(3) 0.0046(3)
C6 0.0202(5) 0.0210(5) 0.0239(5) -0.0008(4) 0.0047(4) -0.0021(4)
N1 0.0238(5) 0.0477(6) 0.0245(5) 0.0065(4) 0.0066(4) 0.0125(4)
N2 0.0247(5) 0.0294(5) 0.0241(5) 0.0016(4) 0.0075(4) 0.0043(4)
O7 0.0231(4) 0.0394(5) 0.0293(4) -0.0015(4) 0.0074(3) 0.0071(3)
C7 0.0215(5) 0.0226(5) 0.0271(5) -0.0025(4) 0.0054(4) 0.0002(4)
N3 0.0227(5) 0.0334(5) 0.0263(5) 0.0001(4) 0.0058(4) 0.0050(4)
N4 0.0279(5) 0.0543(7) 0.0272(5) 0.0067(5) 0.0092(4) 0.0145(5)
O8 0.0224(4) 0.0310(4) 0.0254(4) 0.0027(3) 0.0058(3) 0.0051(3)
C8 0.0195(5) 0.0223(5) 0.0273(5) -0.0013(4) 0.0058(4) -0.0025(4)
N5 0.0265(5) 0.0462(6) 0.0269(5) 0.0049(4) 0.0049(4) 0.0135(4)
N6 0.0273(5) 0.0298(5) 0.0340(5) -0.0016(4) 0.0121(4) 0.0034(4)
O1W 0.0292(4) 0.0332(5) 0.0265(4) 0.0034(3) 0.0030(4) -0.0009(4)
O2W 0.0277(4) 0.0299(5) 0.0283(4) -0.0041(3) 0.0022(4) 0.0009(4)
O3W 0.0353(5) 0.0392(5) 0.0282(5) -0.0024(4) 0.0038(4) -0.0011(4)
O4W 0.0272(4) 0.0355(5) 0.0237(4) 0.0004(3) 0.0049(4) -0.0030(3)
O5W 0.0495(6) 0.0504(6) 0.0273(5) 0.0005(4) 0.0095(4) 0.0108(5)
O6W 0.0354(5) 0.0443(5) 0.0293(5) 0.0036(4) 0.0104(4) 0.0125(4)
O7W 0.0331(5) 0.0345(5) 0.0318(5) 0.0011(4) 0.0128(4) 0.0048(4)
O8W 0.0340(5) 0.0382(5) 0.0285(5) 0.0037(4) 0.0071(4) 0.0105(4)
N7 0.0175(4) 0.0174(4) 0.0198(4) 0.0006(3) 0.0034(3) 0.0001(3)
C9 0.0194(5) 0.0183(5) 0.0237(5) -0.0020(4) 0.0025(4) -0.0024(4)
C10 0.0215(5) 0.0246(5) 0.0310(6) -0.0036(4) -0.0020(4) 0.0018(4)
C11 0.0274(6) 0.0305(6) 0.0338(6) -0.0056(5) -0.0058(5) -0.0008(5)
C12 0.0210(5) 0.0197(5) 0.0221(5) 0.0033(4) 0.0057(4) -0.0009(4)
C13 0.0356(6) 0.0298(6) 0.0302(6) 0.0031(5) 0.0159(5) 0.0048(5)
C14 0.0398(7) 0.0427(7) 0.0341(7) 0.0029(6) 0.0192(6) -0.0042(6)
C15 0.0195(5) 0.0202(5) 0.0249(5) 0.0042(4) 0.0017(4) 0.0026(4)
C16 0.0253(6) 0.0271(6) 0.0383(7) 0.0067(5) -0.0070(5) -0.0027(4)
C17 0.0285(6) 0.0373(7) 0.0349(7) 0.0052(5) -0.0054(5) 0.0053(5)
C18 0.0201(5) 0.0212(5) 0.0217(5) -0.0024(4) 0.0045(4) 0.0006(4)
C19 0.0359(6) 0.0336(6) 0.0291(6) -0.0041(5) 0.0148(5) -0.0084(5)
C20 0.0383(7) 0.0471(8) 0.0263(6) -0.0021(5) 0.0128(5) 0.0046(6)
N8 0.0194(6) 0.0182(6) 0.0192(6) 0.000 0.0048(5) 0.000
C21 0.0225(5) 0.0224(5) 0.0227(5) 0.0033(4) 0.0079(4) -0.0007(4)
C22 0.0593(9) 0.0344(7) 0.0445(8) 0.0123(6) 0.0361(7) 0.0165(6)
C23 0.0533(8) 0.0461(8) 0.0381(7) -0.0023(6) 0.0280(7) -0.0115(6)
C24 0.0227(5) 0.0209(5) 0.0232(5) 0.0030(4) 0.0028(4) 0.0032(4)
C25 0.0313(6) 0.0325(6) 0.0318(6) 0.0018(5) -0.0063(5) -0.0013(5)
C26 0.0350(7) 0.0493(8) 0.0275(6) 0.0010(5) -0.0014(5) 0.0120(6)
N9 0.0174(5) 0.0171(6) 0.0217(6) 0.000 0.0039(5) 0.000
C27 0.0206(5) 0.0203(5) 0.0237(5) -0.0034(4) 0.0058(4) 0.0009(4)
C28 0.0347(6) 0.0304(6) 0.0304(6) -0.0038(5) 0.0154(5) -0.0054(5)
C29 0.0424(7) 0.0419(7) 0.0329(7) -0.0038(5) 0.0184(6) 0.0047(6)
C30 0.0190(5) 0.0204(5) 0.0249(5) -0.0024(4) 0.0021(4) -0.0026(4)
C31 0.0239(5) 0.0289(6) 0.0378(7) -0.0063(5) -0.0059(5) 0.0041(4)
C32 0.0298(6) 0.0450(8) 0.0357(7) -0.0020(6) -0.0074(5) -0.0077(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
O1 C1 1.2431(13) . ?
C1 C2 1.4694(15) . ?
C1 C5 1.4696(15) . ?
O2 C2 1.2412(13) . ?
C2 C3 1.4749(15) . ?
O3 C3 1.2452(13) . ?
C3 C4 1.4650(15) . ?
O4 C4 1.2476(13) . ?
C4 C5 1.4693(15) . ?
O5 C5 1.2376(13) . ?
O6 C6 1.2526(13) . ?
C6 N1 1.3389(15) . ?
C6 N2 1.3456(14) . ?
O7 C7 1.2495(13) . ?
C7 N4 1.3371(15) . ?
C7 N3 1.3517(15) . ?
O8 C8 1.2498(13) . ?
C8 N5 1.3351(15) . ?
C8 N6 1.3524(14) . ?
N7 C9 1.5176(13) . ?
N7 C15 1.5201(13) . ?
N7 C18 1.5222(13) . ?
N7 C12 1.5223(13) . ?
C9 C10 1.5164(15) . ?
C10 C11 1.5186(16) . ?
C12 C13 1.5173(15) . ?
C13 C14 1.5195(17) . ?
C15 C16 1.5121(16) . ?
C16 C17 1.5186(16) . ?
C18 C19 1.5175(15) . ?
C19 C20 1.5178(17) . ?
N8 C24 1.5197(12) 2_655 ?
N8 C24 1.5197(12) . ?
N8 C21 1.5211(12) 2_655 ?
N8 C21 1.5211(12) . ?
C21 C22 1.5098(16) . ?
C22 C23 1.4972(18) . ?
C24 C25 1.5141(16) . ?
C25 C26 1.5170(17) . ?
N9 C30 1.5192(12) 2 ?
N9 C30 1.5192(12) . ?
N9 C27 1.5198(12) . ?
N9 C27 1.5198(12) 2 ?
C27 C28 1.5185(15) . ?
C28 C29 1.5194(17) . ?
C30 C31 1.5136(15) . ?
C31 C32 1.5114(17) . ?

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 C2 125.58(10) . . ?
O1 C1 C5 126.63(10) . . ?
C2 C1 C5 107.78(9) . . ?
O2 C2 C1 124.42(10) . . ?
O2 C2 C3 127.04(10) . . ?
C1 C2 C3 108.53(9) . . ?
O3 C3 C4 125.67(10) . . ?
O3 C3 C2 127.28(10) . . ?
C4 C3 C2 107.05(9) . . ?
O4 C4 C3 126.27(10) . . ?
O4 C4 C5 124.79(10) . . ?
C3 C4 C5 108.94(9) . . ?
O5 C5 C4 125.22(10) . . ?
O5 C5 C1 127.16(10) . . ?
C4 C5 C1 107.62(9) . . ?
O6 C6 N1 121.73(10) . . ?
O6 C6 N2 121.44(10) . . ?
N1 C6 N2 116.81(10) . . ?
O7 C7 N4 121.99(11) . . ?
O7 C7 N3 122.05(11) . . ?
N4 C7 N3 115.92(10) . . ?
O8 C8 N5 122.13(10) . . ?
O8 C8 N6 121.12(11) . . ?
N5 C8 N6 116.74(10) . . ?
C9 N7 C15 106.53(8) . . ?
C9 N7 C18 111.01(7) . . ?
C15 N7 C18 110.90(8) . . ?
C9 N7 C12 110.93(8) . . ?
C15 N7 C12 110.65(8) . . ?
C18 N7 C12 106.88(8) . . ?
C10 C9 N7 115.20(9) . . ?
C9 C10 C11 109.45(9) . . ?
C13 C12 N7 115.44(9) . . ?
C12 C13 C14 110.15(10) . . ?
C16 C15 N7 115.14(9) . . ?
C15 C16 C17 109.79(10) . . ?
C19 C18 N7 115.10(9) . . ?
C18 C19 C20 110.50(10) . . ?
C24 N8 C24 107.07(11) 2_655 . ?
C24 N8 C21 110.57(6) 2_655 2_655 ?
C24 N8 C21 111.11(6) . 2_655 ?
C24 N8 C21 111.11(6) 2_655 . ?
C24 N8 C21 110.57(6) . . ?
C21 N8 C21 106.46(11) 2_655 . ?
C22 C21 N8 115.15(9) . . ?
C23 C22 C21 111.71(11) . . ?
C25 C24 N8 114.92(9) . . ?
C24 C25 C26 110.36(11) . . ?
C30 N9 C30 106.01(11) 2 . ?
C30 N9 C27 111.19(6) 2 . ?
C30 N9 C27 111.21(6) . . ?
C30 N9 C27 111.21(6) 2 2 ?
C30 N9 C27 111.19(6) . 2 ?
C27 N9 C27 106.11(11) . 2 ?
C28 C27 N9 115.86(9) . . ?
C27 C28 C29 109.26(10) . . ?
C31 C30 N9 115.16(9) . . ?
C32 C31 C30 110.32(10) . . ?

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
O1 C1 C2 O2 2.60(18) . . . . ?
C5 C1 C2 O2 -177.11(10) . . . . ?
O1 C1 C2 C3 -177.34(10) . . . . ?
C5 C1 C2 C3 2.94(11) . . . . ?
O2 C2 C3 O3 -1.70(19) . . . . ?
C1 C2 C3 O3 178.24(10) . . . . ?
O2 C2 C3 C4 178.15(11) . . . . ?
C1 C2 C3 C4 -1.91(11) . . . . ?
O3 C3 C4 O4 -0.26(19) . . . . ?
C2 C3 C4 O4 179.89(11) . . . . ?
O3 C3 C4 C5 180.00(10) . . . . ?
C2 C3 C4 C5 0.14(12) . . . . ?
O4 C4 C5 O5 2.00(18) . . . . ?
C3 C4 C5 O5 -178.25(10) . . . . ?
O4 C4 C5 C1 -178.08(11) . . . . ?
C3 C4 C5 C1 1.66(12) . . . . ?
O1 C1 C5 O5 -2.62(19) . . . . ?
C2 C1 C5 O5 177.09(11) . . . . ?
O1 C1 C5 C4 177.47(11) . . . . ?
C2 C1 C5 C4 -2.83(11) . . . . ?
C15 N7 C9 C10 177.83(9) . . . . ?
C18 N7 C9 C10 -61.34(11) . . . . ?
C12 N7 C9 C10 57.33(11) . . . . ?
N7 C9 C10 C11 -172.98(9) . . . . ?
C9 N7 C12 C13 52.80(12) . . . . ?
C15 N7 C12 C13 -65.22(12) . . . . ?
C18 N7 C12 C13 173.94(9) . . . . ?
N7 C12 C13 C14 -179.48(10) . . . . ?
C9 N7 C15 C16 173.50(10) . . . . ?
C18 N7 C15 C16 52.59(12) . . . . ?
C12 N7 C15 C16 -65.83(12) . . . . ?
N7 C15 C16 C17 -178.92(10) . . . . ?
C9 N7 C18 C19 -62.39(11) . . . . ?
C15 N7 C18 C19 55.83(11) . . . . ?
C12 N7 C18 C19 176.52(9) . . . . ?
N7 C18 C19 C20 -172.60(10) . . . . ?
C24 N8 C21 C22 55.61(12) 2_655 . . . ?
C24 N8 C21 C22 -63.14(12) . . . . ?
C21 N8 C21 C22 176.06(12) 2_655 . . . ?
N8 C21 C22 C23 -168.43(11) . . . . ?
C24 N8 C24 C25 175.59(11) 2_655 . . . ?
C21 N8 C24 C25 54.75(12) 2_655 . . . ?
C21 N8 C24 C25 -63.24(11) . . . . ?
N8 C24 C25 C26 -175.02(9) . . . . ?
C30 N9 C27 C28 55.72(11) 2 . . . ?
C30 N9 C27 C28 -62.17(11) . . . . ?
C27 N9 C27 C28 176.78(11) 2 . . . ?
N9 C27 C28 C29 -172.04(9) . . . . ?
C30 N9 C30 C31 175.22(11) 2 . . . ?
C27 N9 C30 C31 -63.80(11) . . . . ?
C27 N9 C30 C31 54.22(11) 2 . . . ?
N9 C30 C31 C32 -178.73(9) . . . . ?

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
O8W H8WB O2W 0.86(2) 1.99(2) 2.7972(13) 155.2(17) 8_556
N6 H3A O2W 0.86 2.19 2.9739(14) 151.7 6_566
N5 H4B O7 0.86 2.16 3.0123(13) 170.3 3_455
N6 H3B O8W 0.86 2.56 3.0654(13) 118.4 3_455
O2W H2WB O7W 0.817(18) 1.940(19) 2.7562(13) 176.0(17) 3_455
N3 H1A O3W 0.86 2.17 3.0183(14) 166.8 2_654
O7W H7WA O3W 0.804(19) 2.047(19) 2.8030(14) 156.6(17) 2_654
O8W H8WA O4W 0.816(18) 2.044(18) 2.8225(13) 159.4(16) 2_655
O4W H4WB O4 0.846(19) 1.962(19) 2.7955(13) 168.4(17) 2_655
N1 H6A O8 0.86 2.10 2.9562(12) 173.9 .
N1 H6B O1 0.86 2.16 3.0110(13) 173.1 .
N2 H5A O1W 0.86 2.18 2.9889(13) 156.4 .
N2 H5B O2 0.86 2.11 2.9423(12) 162.1 .
N3 H1B O3 0.86 2.30 3.1419(13) 166.6 .
N4 H2A O8W 0.86 2.18 2.9635(14) 151.8 .
N4 H2B O4 0.86 1.99 2.8175(13) 160.6 .
N5 H4A O6 0.86 2.06 2.9131(13) 173.7 .
O2W H2WA O6 0.792(19) 2.00(2) 2.7880(12) 174.2(17) .
O3W H3WA O3 0.88(2) 1.93(2) 2.8093(13) 176.8(17) .
O3W H3WB O5W 0.765(16) 1.957(16) 2.7209(16) 178.5(16) .
O4W H4WA O5 0.816(18) 1.913(18) 2.7282(13) 178.5(18) .
O7W H7WB O7 0.856(19) 1.895(19) 2.7503(13) 177.6(17) .
O5W H5WA O2 1.06(2) 1.63(2) 2.6873(13) 171.8(17) .
O5W H5WB O1W 1.07(2) 1.72(2) 2.7746(14) 171(2) .
O6W H6WA O1 0.845(17) 1.945(18) 2.7822(13) 170.8(15) .
O6W H6WB O4W 0.809(19) 2.099(19) 2.8795(14) 162.0(18) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.051
#< End of compound (1) > 

data_compound(2)
_database_code_depnum_ccdc_archive 'CCDC 216681'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis(tetra-n-butylammonium) croconate-1,3-dimethylurea (1/3)
;
_chemical_name_common            
'bis(tetra-n-butylammonium) croconate-1,3-dimethylurea (1/3) '
_chemical_melting_point          '  150-152 deg. (dec) '
_chemical_formula_moiety         [(n-C4H9)4N+]2(C5O5)2-.3(CH3NH)2CO
_chemical_formula_sum            'C46 H96 N8 O8'
_chemical_formula_weight         889.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.211(4)
_cell_length_b                   13.5697(19)
_cell_length_c                   15.775(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.204(18)
_cell_angle_gamma                90.00
_cell_volume                     5388.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            '  pale yellow '
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_correction_T_min  0.894441
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123K
_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  ' Smart Apex CCD'
_diffrn_measurement_method       ' omega scan '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27470
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5304
_reflns_number_gt                4687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'SMART for Windows NT, Bruker AXS Inc., Madison, Wisconsin, USA, 1997.'
_computing_cell_refinement       
;
SAINT-PLUS for Windows NT, Ver. 5.0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 1997.
;
_computing_data_reduction        
;SAINT-PLUS for Windows NT, Ver. 5.0, Bruker AXS Inc., Madison,
Wisconsin, USA, 1997.
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
XP-Interactive Molecular Graphics, Ver. 5.1, Bruker AXS Inc., Madison,
Wisconsin, USA, 1998.
;
_computing_publication_material  
'SHELXTL-Bruker AXS Inc., Madison, Wisconsin, USA, 1998.'

_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^)+(0.0736P)^2^+3.5807P] 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_number_reflns         5304
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.54953(4) 0.76693(7) 0.20510(6) 0.0332(2) Uani 1 1 d . . .
O2 O 0.57766(4) 0.56160(7) 0.17087(6) 0.0350(2) Uani 1 1 d . . .
O3 O 0.5000 0.43374(9) 0.2500 0.0350(3) Uani 1 2 d S . .
C1 C 0.52440(5) 0.69205(9) 0.22728(8) 0.0268(3) Uani 1 1 d . . .
C2 C 0.53921(5) 0.58947(9) 0.21044(8) 0.0278(3) Uani 1 1 d . . .
C3 C 0.5000 0.52506(13) 0.2500 0.0281(4) Uani 1 2 d S . .
O4 O 0.5000 1.11442(9) 0.2500 0.0310(3) Uani 1 2 d S . .
C4 C 0.5000 1.02302(13) 0.2500 0.0276(4) Uani 1 2 d S . .
C5 C 0.54334(6) 1.01577(11) 0.11580(9) 0.0381(3) Uani 1 1 d . . .
H5A H 0.5567 0.9662 0.0791 0.057 Uiso 1 1 calc R . .
H5B H 0.5718 1.0591 0.1345 0.057 Uiso 1 1 calc R . .
H5C H 0.5160 1.0530 0.0854 0.057 Uiso 1 1 calc R . .
N1 N 0.52166(5) 0.96924(8) 0.18839(8) 0.0355(3) Uani 1 1 d . . .
H1A H 0.5225 0.9061 0.1927 0.043 Uiso 1 1 calc R . .
O5 O 0.73819(4) 0.77625(10) 0.13091(8) 0.0520(3) Uani 1 1 d . . .
C6 C 0.69085(6) 0.75659(14) 0.13805(9) 0.0402(4) Uani 1 1 d . . .
C7 C 0.67422(7) 0.92055(15) 0.19007(12) 0.0538(4) Uani 1 1 d . . .
H7A H 0.6446 0.9617 0.2020 0.081 Uiso 1 1 calc R . .
H7B H 0.6944 0.9513 0.1476 0.081 Uiso 1 1 calc R . .
H7C H 0.6964 0.9115 0.2410 0.081 Uiso 1 1 calc R . .
C8 C 0.70696(8) 0.58392(16) 0.11267(13) 0.0586(5) Uani 1 1 d . . .
H8A H 0.6869 0.5244 0.1028 0.088 Uiso 1 1 calc R . .
H8B H 0.7297 0.5767 0.1631 0.088 Uiso 1 1 calc R . .
H8C H 0.7281 0.5966 0.0651 0.088 Uiso 1 1 calc R . .
N2 N 0.65513(5) 0.82607(11) 0.15958(8) 0.0454(3) Uani 1 1 d . . .
H2A H 0.6216 0.8139 0.1551 0.054 Uiso 1 1 calc R . .
N3 N 0.67098(5) 0.66521(11) 0.12317(8) 0.0454(3) Uani 1 1 d . . .
H3A H 0.6372 0.6556 0.1200 0.054 Uiso 1 1 calc R . .
N4 N 0.38958(4) 0.27540(7) 0.13286(6) 0.0229(2) Uani 1 1 d . . .
C9 C 0.36129(5) 0.18580(9) 0.09437(8) 0.0254(3) Uani 1 1 d . . .
H9A H 0.3256 0.1839 0.1142 0.030 Uiso 1 1 calc R . .
H9B H 0.3582 0.1940 0.0332 0.030 Uiso 1 1 calc R . .
C10 C 0.38782(5) 0.08739(9) 0.11424(9) 0.0294(3) Uani 1 1 d . . .
H10A H 0.3900 0.0768 0.1752 0.035 Uiso 1 1 calc R . .
H10B H 0.4237 0.0882 0.0950 0.035 Uiso 1 1 calc R . .
C11 C 0.35669(6) 0.00355(10) 0.07085(9) 0.0359(3) Uani 1 1 d . . .
H11A H 0.3220 -0.0007 0.0942 0.043 Uiso 1 1 calc R . .
H11B H 0.3515 0.0180 0.0107 0.043 Uiso 1 1 calc R . .
C12 C 0.38474(7) -0.09525(11) 0.08197(11) 0.0452(4) Uani 1 1 d . . .
H12A H 0.3637 -0.1457 0.0537 0.068 Uiso 1 1 calc R . .
H12B H 0.3893 -0.1106 0.1413 0.068 Uiso 1 1 calc R . .
H12C H 0.4188 -0.0919 0.0579 0.068 Uiso 1 1 calc R . .
C13 C 0.39285(5) 0.27058(9) 0.22935(8) 0.0250(3) Uani 1 1 d . . .
H13A H 0.4147 0.2146 0.2470 0.030 Uiso 1 1 calc R . .
H13B H 0.4106 0.3295 0.2512 0.030 Uiso 1 1 calc R . .
C14 C 0.33975(5) 0.26155(11) 0.26932(8) 0.0324(3) Uani 1 1 d . . .
H14A H 0.3251 0.1965 0.2581 0.039 Uiso 1 1 calc R . .
H14B H 0.3152 0.3097 0.2442 0.039 Uiso 1 1 calc R . .
C15 C 0.34607(6) 0.27811(14) 0.36441(9) 0.0423(4) Uani 1 1 d . . .
H15A H 0.3714 0.2310 0.3890 0.051 Uiso 1 1 calc R . .
H15B H 0.3602 0.3437 0.3753 0.051 Uiso 1 1 calc R . .
C16 C 0.29399(7) 0.26749(17) 0.40716(11) 0.0582(5) Uani 1 1 d . . .
H16A H 0.2999 0.2786 0.4671 0.087 Uiso 1 1 calc R . .
H16B H 0.2802 0.2023 0.3976 0.087 Uiso 1 1 calc R . .
H16C H 0.2690 0.3149 0.3839 0.087 Uiso 1 1 calc R . .
C17 C 0.35716(5) 0.36402(9) 0.10071(8) 0.0248(3) Uani 1 1 d . . .
H17A H 0.3602 0.3689 0.0398 0.030 Uiso 1 1 calc R . .
H17B H 0.3201 0.3516 0.1105 0.030 Uiso 1 1 calc R . .
C18 C 0.37254(5) 0.46277(9) 0.14022(9) 0.0286(3) Uani 1 1 d . . .
H18A H 0.4089 0.4786 0.1281 0.034 Uiso 1 1 calc R . .
H18B H 0.3704 0.4592 0.2014 0.034 Uiso 1 1 calc R . .
C19 C 0.33524(5) 0.54308(10) 0.10430(9) 0.0317(3) Uani 1 1 d . . .
H19A H 0.3389 0.5483 0.0436 0.038 Uiso 1 1 calc R . .
H19B H 0.2988 0.5244 0.1133 0.038 Uiso 1 1 calc R . .
C20 C 0.34656(6) 0.64275(10) 0.14513(10) 0.0384(3) Uani 1 1 d . . .
H20A H 0.3223 0.6907 0.1207 0.058 Uiso 1 1 calc R . .
H20B H 0.3823 0.6622 0.1354 0.058 Uiso 1 1 calc R . .
H20C H 0.3422 0.6383 0.2051 0.058 Uiso 1 1 calc R . .
C21 C 0.44679(5) 0.28183(9) 0.10700(8) 0.0250(3) Uani 1 1 d . . .
H21A H 0.4618 0.3433 0.1285 0.030 Uiso 1 1 calc R . .
H21B H 0.4668 0.2287 0.1347 0.030 Uiso 1 1 calc R . .
C22 C 0.45472(5) 0.27649(11) 0.01215(9) 0.0322(3) Uani 1 1 d . . .
H22A H 0.4367 0.3314 -0.0164 0.039 Uiso 1 1 calc R . .
H22B H 0.4394 0.2159 -0.0108 0.039 Uiso 1 1 calc R . .
C23 C 0.51398(6) 0.27991(10) -0.00370(9) 0.0338(3) Uani 1 1 d . . .
H23A H 0.5326 0.2335 0.0340 0.041 Uiso 1 1 calc R . .
H23B H 0.5190 0.2591 -0.0615 0.041 Uiso 1 1 calc R . .
C24 C 0.53838(6) 0.38114(12) 0.00982(11) 0.0444(4) Uani 1 1 d . . .
H24A H 0.5754 0.3786 -0.0010 0.067 Uiso 1 1 calc R . .
H24B H 0.5344 0.4017 0.0673 0.067 Uiso 1 1 calc R . .
H24C H 0.5208 0.4273 -0.0283 0.067 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 0.0313(5) 0.0230(5) 0.0455(6) 0.0025(4) 0.0055(4) -0.0013(4)
O2 0.0347(5) 0.0303(5) 0.0399(6) -0.0045(4) 0.0020(4) 0.0051(4)
O3 0.0376(7) 0.0203(6) 0.0458(8) 0.000 -0.0098(6) 0.000
C1 0.0272(6) 0.0236(6) 0.0291(6) 0.0004(5) -0.0041(5) 0.0006(5)
C2 0.0278(6) 0.0252(6) 0.0295(6) -0.0007(5) -0.0059(5) 0.0022(5)
C3 0.0296(9) 0.0226(9) 0.0308(9) 0.000 -0.0110(7) 0.000
O4 0.0371(7) 0.0198(6) 0.0354(7) 0.000 -0.0036(6) 0.000
C4 0.0292(9) 0.0221(8) 0.0310(9) 0.000 -0.0041(7) 0.000
C5 0.0435(8) 0.0342(7) 0.0369(8) 0.0019(6) 0.0060(6) 0.0032(6)
N1 0.0492(7) 0.0206(5) 0.0373(7) 0.0011(5) 0.0082(5) 0.0031(5)
O5 0.0265(6) 0.0839(9) 0.0457(7) -0.0115(6) 0.0029(5) -0.0035(5)
C6 0.0269(7) 0.0696(11) 0.0238(7) -0.0021(7) -0.0006(5) -0.0015(7)
C7 0.0445(9) 0.0679(12) 0.0490(10) -0.0033(9) 0.0021(8) 0.0003(8)
C8 0.0481(10) 0.0728(13) 0.0539(11) -0.0174(9) -0.0065(8) 0.0056(9)
N2 0.0263(6) 0.0683(10) 0.0416(7) 0.0015(6) 0.0030(5) -0.0008(6)
N3 0.0293(6) 0.0706(10) 0.0360(7) -0.0064(6) -0.0004(5) 0.0003(6)
N4 0.0248(5) 0.0206(5) 0.0233(5) 0.0000(4) 0.0006(4) -0.0008(4)
C9 0.0264(6) 0.0242(6) 0.0253(6) -0.0028(5) -0.0004(5) -0.0041(5)
C10 0.0340(7) 0.0222(6) 0.0318(7) -0.0019(5) 0.0008(5) -0.0021(5)
C11 0.0418(8) 0.0268(7) 0.0391(8) -0.0051(6) 0.0018(6) -0.0058(6)
C12 0.0634(10) 0.0245(7) 0.0483(9) -0.0060(6) 0.0081(8) -0.0025(7)
C13 0.0284(6) 0.0244(6) 0.0218(6) 0.0008(5) -0.0013(5) -0.0004(5)
C14 0.0294(7) 0.0422(8) 0.0255(7) 0.0004(5) 0.0012(5) -0.0043(6)
C15 0.0354(8) 0.0642(11) 0.0273(7) -0.0026(7) 0.0026(6) -0.0038(7)
C16 0.0445(9) 0.0988(16) 0.0323(8) -0.0051(9) 0.0105(7) -0.0075(10)
C17 0.0259(6) 0.0233(6) 0.0249(6) 0.0016(5) -0.0009(5) 0.0012(5)
C18 0.0316(7) 0.0230(6) 0.0305(7) 0.0007(5) -0.0027(5) 0.0006(5)
C19 0.0310(7) 0.0260(7) 0.0378(7) 0.0016(5) -0.0023(6) 0.0016(5)
C20 0.0478(8) 0.0264(7) 0.0403(8) 0.0004(6) -0.0043(6) 0.0072(6)
C21 0.0230(6) 0.0237(6) 0.0281(6) 0.0003(5) 0.0011(5) -0.0009(5)
C22 0.0315(7) 0.0367(7) 0.0285(7) -0.0009(5) 0.0033(5) -0.0026(6)
C23 0.0338(7) 0.0376(8) 0.0307(7) 0.0043(6) 0.0071(6) 0.0059(6)
C24 0.0367(8) 0.0485(9) 0.0484(9) 0.0084(7) 0.0070(7) -0.0063(7)

_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 C1 1.2574(16) . ?
O2 C2 1.2409(17) . ?
O3 C3 1.239(2) . ?
C1 C1 1.458(3) 2_655 ?
C1 C2 1.4693(18) . ?
C2 C3 1.4831(17) . ?
C3 C2 1.4831(17) 2_655 ?
O4 C4 1.240(2) . ?
C4 N1 1.3545(15) . ?
C4 N1 1.3545(15) 2_655 ?
C5 N1 1.4418(19) . ?
O5 C6 1.2340(18) . ?
C6 N3 1.353(2) . ?
C6 N2 1.360(2) . ?
C7 N2 1.442(2) . ?
C8 N3 1.444(2) . ?
N4 C9 1.5190(15) . ?
N4 C13 1.5211(15) . ?
N4 C21 1.5231(16) . ?
N4 C17 1.5247(15) . ?
C9 C10 1.5185(18) . ?
C10 C11 1.5227(18) . ?
C11 C12 1.521(2) . ?
C13 C14 1.5162(18) . ?
C14 C15 1.5163(19) . ?
C15 C16 1.516(2) . ?
C17 C18 1.5190(17) . ?
C18 C19 1.5275(18) . ?
C19 C20 1.5181(19) . ?
C21 C22 1.5224(18) . ?
C22 C23 1.5293(19) . ?
C23 C24 1.515(2) . ?

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 C1 126.08(7) . 2_655 ?
O1 C1 C2 125.32(12) . . ?
C1 C1 C2 108.59(7) 2_655 . ?
O2 C2 C1 126.39(12) . . ?
O2 C2 C3 126.15(12) . . ?
C1 C2 C3 107.46(11) . . ?
O3 C3 C2 126.11(8) . . ?
O3 C3 C2 126.11(8) . 2_655 ?
C2 C3 C2 107.79(15) . 2_655 ?
O4 C4 N1 122.60(8) . . ?
O4 C4 N1 122.60(8) . 2_655 ?
N1 C4 N1 114.79(16) . 2_655 ?
C4 N1 C5 121.33(12) . . ?
O5 C6 N3 122.21(15) . . ?
O5 C6 N2 122.02(16) . . ?
N3 C6 N2 115.76(13) . . ?
C6 N2 C7 119.09(13) . . ?
C6 N3 C8 119.42(14) . . ?
C9 N4 C13 111.32(9) . . ?
C9 N4 C21 111.67(9) . . ?
C13 N4 C21 105.74(9) . . ?
C9 N4 C17 105.51(9) . . ?
C13 N4 C17 111.39(9) . . ?
C21 N4 C17 111.33(9) . . ?
C10 C9 N4 115.46(10) . . ?
C9 C10 C11 110.74(11) . . ?
C12 C11 C10 112.46(12) . . ?
C14 C13 N4 114.83(10) . . ?
C13 C14 C15 110.68(11) . . ?
C16 C15 C14 112.35(13) . . ?
C18 C17 N4 116.08(10) . . ?
C17 C18 C19 109.85(11) . . ?
C20 C19 C18 112.40(11) . . ?
C22 C21 N4 116.03(10) . . ?
C21 C22 C23 110.03(11) . . ?
C24 C23 C22 113.39(12) . . ?

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
O1 C1 C2 O2 -1.5(2) . . . . ?
C1 C1 C2 O2 177.76(13) 2_655 . . . ?
O1 C1 C2 C3 178.07(11) . . . . ?
C1 C1 C2 C3 -2.67(16) 2_655 . . . ?
O2 C2 C3 O3 0.58(15) . . . . ?
C1 C2 C3 O3 -178.99(6) . . . . ?
O2 C2 C3 C2 -179.42(15) . . . 2_655 ?
C1 C2 C3 C2 1.01(6) . . . 2_655 ?
O4 C4 N1 C5 -3.83(15) . . . . ?
N1 C4 N1 C5 176.17(15) 2_655 . . . ?
O5 C6 N2 C7 -11.6(2) . . . . ?
N3 C6 N2 C7 169.77(14) . . . . ?
O5 C6 N3 C8 10.7(2) . . . . ?
N2 C6 N3 C8 -170.66(14) . . . . ?
C13 N4 C9 C10 -61.66(13) . . . . ?
C21 N4 C9 C10 56.28(13) . . . . ?
C17 N4 C9 C10 177.37(10) . . . . ?
N4 C9 C10 C11 -178.74(11) . . . . ?
C9 C10 C11 C12 174.40(12) . . . . ?
C9 N4 C13 C14 -57.29(14) . . . . ?
C21 N4 C13 C14 -178.75(10) . . . . ?
C17 N4 C13 C14 60.17(13) . . . . ?
N4 C13 C14 C15 -168.50(12) . . . . ?
C13 C14 C15 C16 -178.75(14) . . . . ?
C9 N4 C17 C18 171.49(10) . . . . ?
C13 N4 C17 C18 50.56(14) . . . . ?
C21 N4 C17 C18 -67.20(13) . . . . ?
N4 C17 C18 C19 -177.74(11) . . . . ?
C17 C18 C19 C20 176.68(12) . . . . ?
C9 N4 C21 C22 52.48(14) . . . . ?
C13 N4 C21 C22 173.72(10) . . . . ?
C17 N4 C21 C22 -65.16(13) . . . . ?
N4 C21 C22 C23 -177.85(10) . . . . ?
C21 C22 C23 C24 -73.64(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 H1A O1 0.86 2.01 2.8423(15) 161.6 .
N2 H2A O1 0.86 2.12 2.9088(17) 152.4 .
N3 H3A O2 0.86 2.16 2.8769(18) 140.8 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043

# End of compound (2)