 
data_06skc0068p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Oxalic acid & 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H14 N4 O6'
_chemical_formula_weight          262.23
 
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    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                    8.322(4)
_cell_length_b                    11.203(5)
_cell_length_c                    11.915(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.79(3)
_cell_angle_gamma                 90.00
_cell_volume                      1100.6(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2546
_cell_measurement_theta_min       0.41
_cell_measurement_theta_max       28.28
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.583
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              552
_exptl_absorpt_coefficient_mu     0.136
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9865
_exptl_absorpt_correction_T_max   0.9986
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15954
_diffrn_reflns_av_R_equivalents   0.1842
_diffrn_reflns_av_sigmaI/netI     0.1022
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.07
_diffrn_reflns_theta_max          25.00
_reflns_number_total              1934
_reflns_number_gt                 1265
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0000P)²+9.0267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1934
_refine_ls_number_parameters      153
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2012
_refine_ls_R_factor_gt            0.1421
_refine_ls_wR_factor_ref          0.2343
_refine_ls_wR_factor_gt           0.2116
_refine_ls_goodness_of_fit_ref    1.243
_refine_ls_restrained_S_all       1.243
_refine_ls_shift/su_max           0.003
_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 -0.2026(9) -0.1130(7) 0.4687(6) 0.0186(12) Uani 1 1 d . . .
C2 C -0.2938(9) -0.1534(7) 0.5644(6) 0.0186(12) Uani 1 1 d . . .
O1A O -0.1413(6) -0.1852(5) 0.4105(4) 0.0223(13) Uani 1 1 d . . .
O1B O -0.2003(6) 0.0022(5) 0.4570(5) 0.0203(13) Uani 1 1 d . . .
H1 H -0.1438 0.0202 0.4062 0.030 Uiso 1 1 calc R . .
O2A O -0.2945(7) -0.2683(5) 0.5775(4) 0.0209(13) Uani 1 1 d . . .
H2 H -0.3415 -0.2854 0.6335 0.031 Uiso 1 1 calc R . .
O2B O -0.3593(6) -0.0840(5) 0.6199(4) 0.0214(13) Uani 1 1 d . . .
C22 C -0.0253(10) -0.0242(8) 0.7596(7) 0.024(2) Uani 1 1 d . . .
C24 C -0.0981(9) 0.1354(7) 0.8617(6) 0.0200(13) Uani 1 1 d . . .
H24A H -0.1758 0.2018 0.8439 0.024 Uiso 1 1 calc R . .
H24B H -0.0094 0.1615 0.9204 0.024 Uiso 1 1 calc R . .
C25 C -0.1828(10) 0.0220(7) 0.8983(7) 0.0200(13) Uani 1 1 d . . .
H25A H -0.1701 0.0139 0.9818 0.024 Uiso 1 1 calc R . .
H25B H -0.2995 0.0210 0.8679 0.024 Uiso 1 1 calc R . .
N21 N -0.0932(8) -0.0699(6) 0.8465(5) 0.0219(16) Uani 1 1 d . . .
H21 H -0.0847 -0.1447 0.8689 0.026 Uiso 1 1 calc R . .
N23 N -0.0357(8) 0.0918(6) 0.7603(6) 0.0268(18) Uani 1 1 d . . .
H23 H -0.0085 0.1383 0.7064 0.032 Uiso 1 1 calc R . .
O22 O 0.0395(7) -0.0884(5) 0.6900(4) 0.0231(14) Uani 1 1 d . . .
C32 C -0.5205(9) -0.2108(7) 0.2907(6) 0.0173(19) Uani 1 1 d . . .
C34 C -0.6098(10) -0.3733(8) 0.3830(6) 0.024(2) Uani 1 1 d . . .
H34A H -0.5251 -0.4121 0.4372 0.028 Uiso 1 1 calc R . .
H34B H -0.6995 -0.4304 0.3615 0.028 Uiso 1 1 calc R . .
C35 C -0.6704(10) -0.2591(7) 0.4315(7) 0.025(2) Uani 1 1 d . . .
H35A H -0.7889 -0.2500 0.4105 0.030 Uiso 1 1 calc R . .
H35B H -0.6443 -0.2574 0.5151 0.030 Uiso 1 1 calc R . .
N31 N -0.5828(8) -0.1674(6) 0.3796(5) 0.0196(15) Uani 1 1 d . . .
H31 H -0.5720 -0.0932 0.4035 0.024 Uiso 1 1 calc R . .
N33 N -0.5444(8) -0.3293(6) 0.2851(5) 0.0206(16) Uani 1 1 d . . .
H33 H -0.5229 -0.3745 0.2286 0.025 Uiso 1 1 calc R . .
O32 O -0.4552(6) -0.1510(5) 0.2210(4) 0.0226(13) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2)
C2 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2)
O1A 0.027(3) 0.019(3) 0.024(3) -0.004(2) 0.013(2) 0.004(3)
O1B 0.021(3) 0.014(3) 0.029(3) -0.001(2) 0.016(3) -0.001(2)
O2A 0.022(3) 0.018(3) 0.023(3) -0.001(2) 0.004(2) -0.010(2)
O2B 0.023(3) 0.022(3) 0.021(3) -0.004(2) 0.011(3) -0.003(3)
C22 0.021(5) 0.025(5) 0.025(5) 0.006(4) 0.000(4) 0.000(4)
C24 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3)
C25 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3)
N21 0.025(4) 0.020(4) 0.022(4) 0.008(3) 0.008(3) 0.007(3)
N23 0.042(5) 0.019(4) 0.021(4) 0.004(3) 0.010(3) 0.000(3)
O22 0.034(3) 0.020(3) 0.017(3) -0.004(3) 0.009(3) 0.006(3)
C32 0.009(4) 0.017(5) 0.024(5) -0.010(4) -0.003(4) 0.004(3)
C34 0.018(4) 0.033(5) 0.021(4) -0.001(4) 0.006(4) 0.005(4)
C35 0.021(5) 0.029(5) 0.026(5) 0.003(4) 0.005(4) 0.001(4)
N31 0.023(4) 0.014(4) 0.022(4) 0.000(3) 0.005(3) 0.001(3)
N33 0.024(4) 0.020(4) 0.019(4) -0.007(3) 0.006(3) -0.005(3)
O32 0.025(3) 0.021(3) 0.021(3) 0.003(2) 0.000(3) -0.001(3)
 
_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 O1A 1.221(9) . ?
C1 O1B 1.298(9) . ?
C1 C2 1.522(10) . ?
C2 O2B 1.199(9) . ?
C2 O2A 1.297(9) . ?
O1B H1 0.8400 . ?
O2A H2 0.8400 . ?
C22 O22 1.272(10) . ?
C22 N23 1.303(11) . ?
C22 N21 1.346(10) . ?
C24 N23 1.462(9) . ?
C24 C25 1.544(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.457(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.248(9) . ?
C32 N31 1.333(9) . ?
C32 N33 1.343(10) . ?
C34 N33 1.439(10) . ?
C34 C35 1.517(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N31 1.446(10) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 0.8800 . ?
N33 H33 0.8800 . ?
 
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
O1A C1 O1B 125.8(7) . . ?
O1A C1 C2 121.1(7) . . ?
O1B C1 C2 113.1(7) . . ?
O2B C2 O2A 124.5(7) . . ?
O2B C2 C1 122.1(7) . . ?
O2A C2 C1 113.4(7) . . ?
C1 O1B H1 109.5 . . ?
C2 O2A H2 109.5 . . ?
O22 C22 N23 127.1(8) . . ?
O22 C22 N21 123.1(8) . . ?
N23 C22 N21 109.8(8) . . ?
N23 C24 C25 100.7(6) . . ?
N23 C24 H24A 111.6 . . ?
C25 C24 H24A 111.6 . . ?
N23 C24 H24B 111.6 . . ?
C25 C24 H24B 111.6 . . ?
H24A C24 H24B 109.4 . . ?
N21 C25 C24 100.5(6) . . ?
N21 C25 H25A 111.7 . . ?
C24 C25 H25A 111.7 . . ?
N21 C25 H25B 111.7 . . ?
C24 C25 H25B 111.7 . . ?
H25A C25 H25B 109.4 . . ?
C22 N21 C25 110.5(7) . . ?
C22 N21 H21 124.8 . . ?
C25 N21 H21 124.8 . . ?
C22 N23 C24 111.7(7) . . ?
C22 N23 H23 124.1 . . ?
C24 N23 H23 124.1 . . ?
O32 C32 N31 125.8(7) . . ?
O32 C32 N33 125.0(7) . . ?
N31 C32 N33 109.2(7) . . ?
N33 C34 C35 101.7(7) . . ?
N33 C34 H34A 111.4 . . ?
C35 C34 H34A 111.4 . . ?
N33 C34 H34B 111.4 . . ?
C35 C34 H34B 111.4 . . ?
H34A C34 H34B 109.3 . . ?
N31 C35 C34 102.9(6) . . ?
N31 C35 H35A 111.2 . . ?
C34 C35 H35A 111.2 . . ?
N31 C35 H35B 111.2 . . ?
C34 C35 H35B 111.2 . . ?
H35A C35 H35B 109.1 . . ?
C32 N31 C35 110.7(7) . . ?
C32 N31 H31 124.6 . . ?
C35 N31 H31 124.6 . . ?
C32 N33 C34 111.6(6) . . ?
C32 N33 H33 124.2 . . ?
C34 N33 H33 124.2 . . ?
 
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
 _geom_hbond_site_symmetry_A
O1B H1 O22  0.84 1.71 2.535(8) 167.3 3_556
N23 H23 O1A  0.88 2.06 2.867(8) 152.1 3_556
O2A H2 O32  0.84 1.66 2.480(8) 164.4 4_556
N21 H21 O1A  0.88 2.04 2.890(8) 162.2 4_556
N31 H31 O2B  0.88 2.07 2.858(8) 147.9 3_456
N33 H33 O2B  0.88 2.06 2.831(8) 146.5 4
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.360
_refine_diff_density_min   -0.354
_refine_diff_density_rms    0.093
