#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:09:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180126 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/24/7102461.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7102461
loop_
_publ_author_name
'Lam, Chi-Keung'
'Cheng, Mei-Fun'
'Li, Chi-Lun'
'Zhang, Jie-Peng'
'Chen, Xiao-Ming'
'Li, Wai-Kee'
'Mak, Thomas C W'
_publ_section_title
;
 Stabilization of D5h and C2v valence tautomers of the croconate
 dianion.
;
_journal_issue                   4
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              448
_journal_page_last               449
_journal_paper_doi               10.1039/b312545a
_journal_year                    2004
_chemical_formula_moiety         '[(n-C4H9)4N+]2(C5O5)2-.3(CH3NH)2CO'
_chemical_formula_sum            'C46 H96 N8 O8'
_chemical_formula_weight         889.31
_chemical_melting_point          424.1(10)
_chemical_name_common
'bis(tetra-n-butylammonium) croconate-1,3-dimethylurea (1/3) '
_chemical_name_systematic
;
bis(tetra-n-butylammonium) croconate-1,3-dimethylurea (1/3)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.204(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.211(4)
_cell_length_b                   13.5697(19)
_cell_length_c                   15.775(2)
_cell_measurement_temperature    123
_cell_volume                     5388.4(14)
_computing_cell_refinement
;
SAINT-PLUS for Windows NT, Ver. 5.0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 1997.
;
_computing_data_collection
'SMART for Windows NT, 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_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.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ' Smart Apex CCD'
_diffrn_measurement_method       ' omega scan '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27470
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.894441
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            '  pale yellow '
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0736P)²+3.5807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                4687
_reflns_number_total             5304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b312545a.txt
_cod_data_source_block           compound(2)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '123K' was changed to '123' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as ' 150-152 deg. (dec) '. The value ' 150-152 deg. (dec) ' was changed 
to '424.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Adriana Da\<skevi\<c, 2011-06-14
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7102461
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'
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
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_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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
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
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_4
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) . .
