 
data_06skc0046c2c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Malonic acid & 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H22 N6 O7'
_chemical_formula_weight          362.36
 
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                    16.6403(10)
_cell_length_b                    14.4382(5)
_cell_length_c                    7.6872(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  117.299(2)
_cell_angle_gamma                 90.00
_cell_volume                      1641.20(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1896
_cell_measurement_theta_min       1.02
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.467
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              768
_exptl_absorpt_coefficient_mu     0.121
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9785
_exptl_absorpt_correction_T_max   0.9880
_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    'graphite'
_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             10719
_diffrn_reflns_av_R_equivalents   0.0559
_diffrn_reflns_av_sigmaI/netI     0.0481
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1868
_reflns_number_gt                 1411
_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)+(0.0169P)²+32.0327P] 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      SHELXL
_refine_ls_extinction_coef        0.017(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1868
_refine_ls_number_parameters      117
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1392
_refine_ls_R_factor_gt            0.1115
_refine_ls_wR_factor_ref          0.2739
_refine_ls_wR_factor_gt           0.2629
_refine_ls_goodness_of_fit_ref    1.169
_refine_ls_restrained_S_all       1.169
_refine_ls_shift/su_max           0.024
_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
C2 C 0.0000 0.2578(5) 0.7500 0.0217(16) Uani 1 2 d S . .
H2A H 0.0190 0.2983 0.8661 0.026 Uiso 0.50 1 calc PR . .
H2B H -0.0190 0.2983 0.6339 0.026 Uiso 0.50 1 calc PR . .
C1 C 0.0810(4) 0.2012(4) 0.7720(9) 0.0239(13) Uani 1 1 d . . .
O1A O 0.0988(3) 0.1243(3) 0.8403(7) 0.0315(11) Uani 1 1 d . . .
O1B O 0.1314(3) 0.2499(3) 0.7125(7) 0.0301(11) Uani 1 1 d . . .
H1 H 0.1838 0.2275 0.7611 0.045 Uiso 1 1 calc R . .
C22 C 0.3005(4) 0.0983(4) 0.7982(9) 0.0232(12) Uani 1 1 d . . .
C24 C 0.2751(4) -0.0591(4) 0.8004(9) 0.0257(13) Uani 1 1 d . . .
H24A H 0.2371 -0.1001 0.6897 0.031 Uiso 1 1 calc R . .
H24B H 0.2806 -0.0862 0.9236 0.031 Uiso 1 1 calc R . .
C25 C 0.3690(4) -0.0435(4) 0.8103(9) 0.0271(13) Uani 1 1 d . . .
H25A H 0.4170 -0.0762 0.9235 0.032 Uiso 1 1 calc R . .
H25B H 0.3700 -0.0642 0.6886 0.032 Uiso 1 1 calc R . .
N21 N 0.3791(3) 0.0576(3) 0.8337(8) 0.0262(12) Uani 1 1 d . . .
H21 H 0.4301 0.0876 0.8667 0.031 Uiso 1 1 calc R . .
N23 N 0.2381(3) 0.0338(3) 0.7710(8) 0.0294(12) Uani 1 1 d . . .
H23 H 0.1813 0.0464 0.7392 0.035 Uiso 1 1 calc R . .
O22 O 0.2885(3) 0.1846(3) 0.7912(7) 0.0313(11) Uani 1 1 d . . .
C32 C 0.5000 0.2480(5) 0.7500 0.0208(16) Uani 1 2 d S . .
C35 C 0.4524(4) 0.3997(4) 0.7473(10) 0.0283(14) Uani 1 1 d . . .
H35A H 0.4519 0.4390 0.8523 0.034 Uiso 1 1 calc R . .
H35B H 0.4047 0.4210 0.6190 0.034 Uiso 1 1 calc R . .
N31 N 0.4416(3) 0.3011(3) 0.7803(8) 0.0264(12) Uani 1 1 d . . .
H31 H 0.4017 0.2797 0.8155 0.032 Uiso 1 1 calc R . .
O32 O 0.5000 0.1620(4) 0.7500 0.0273(14) Uani 1 2 d S . .
 
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
C2 0.018(4) 0.018(4) 0.030(4) 0.000 0.011(3) 0.000
C1 0.019(3) 0.024(3) 0.028(3) 0.001(2) 0.010(2) 0.001(2)
O1A 0.028(2) 0.023(2) 0.051(3) 0.0097(19) 0.024(2) 0.0048(17)
O1B 0.026(2) 0.026(2) 0.047(3) 0.0078(19) 0.023(2) 0.0024(17)
C22 0.022(3) 0.018(3) 0.031(3) 0.000(2) 0.013(2) 0.000(2)
C24 0.026(3) 0.021(3) 0.028(3) -0.003(2) 0.010(2) -0.004(2)
C25 0.028(3) 0.020(3) 0.034(3) 0.001(2) 0.015(3) 0.004(2)
N21 0.022(2) 0.020(2) 0.035(3) -0.003(2) 0.012(2) -0.0016(19)
N23 0.019(2) 0.024(3) 0.044(3) 0.002(2) 0.014(2) 0.000(2)
O22 0.024(2) 0.019(2) 0.051(3) -0.0011(19) 0.019(2) 0.0020(17)
C32 0.020(4) 0.020(4) 0.022(4) 0.000 0.009(3) 0.000
C35 0.030(3) 0.019(3) 0.035(3) 0.004(2) 0.014(3) 0.003(2)
N31 0.026(3) 0.024(3) 0.034(3) 0.000(2) 0.018(2) 0.001(2)
O32 0.024(3) 0.021(3) 0.040(4) 0.000 0.018(3) 0.000
 
_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
C2 C1 1.518(7) 2_556 ?
C2 C1 1.518(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 O1A 1.205(7) . ?
C1 O1B 1.325(7) . ?
O1B H1 0.8400 . ?
C22 O22 1.260(7) . ?
C22 N23 1.338(7) . ?
C22 N21 1.342(7) . ?
C24 N23 1.450(7) . ?
C24 C25 1.546(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.471(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.242(10) . ?
C32 N31 1.340(6) . ?
C32 N31 1.340(6) 2_656 ?
C35 N31 1.471(7) . ?
C35 C35 1.564(12) 2_656 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 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
C1 C2 C1 114.9(6) 2_556 . ?
C1 C2 H2A 108.5 2_556 . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 2_556 . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O1A C1 O1B 124.8(5) . . ?
O1A C1 C2 124.9(5) . . ?
O1B C1 C2 110.2(5) . . ?
C1 O1B H1 109.5 . . ?
O22 C22 N23 125.7(5) . . ?
O22 C22 N21 124.2(5) . . ?
N23 C22 N21 110.0(5) . . ?
N23 C24 C25 102.7(4) . . ?
N23 C24 H24A 111.2 . . ?
C25 C24 H24A 111.2 . . ?
N23 C24 H24B 111.2 . . ?
C25 C24 H24B 111.2 . . ?
H24A C24 H24B 109.1 . . ?
N21 C25 C24 101.9(5) . . ?
N21 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N21 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 111.3(5) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 112.0(5) . . ?
C22 N23 H23 124.0 . . ?
C24 N23 H23 124.0 . . ?
O32 C32 N31 124.9(3) . . ?
O32 C32 N31 124.9(3) . 2_656 ?
N31 C32 N31 110.2(7) . 2_656 ?
N31 C35 C35 101.4(3) . 2_656 ?
N31 C35 H35A 111.5 . . ?
C35 C35 H35A 111.5 2_656 . ?
N31 C35 H35B 111.5 . . ?
C35 C35 H35B 111.5 2_656 . ?
H35A C35 H35B 109.3 . . ?
C32 N31 C35 111.6(5) . . ?
C32 N31 H31 124.2 . . ?
C35 N31 H31 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 1.76 2.576(6) 163.0 .
N21 H21 O32  0.88 2.07 2.814(6) 142.3 .
N23 H23 O1A  0.88 2.18 2.914(7) 141.3 .
N31 H31 O22  0.88 2.27 3.086(6) 154.5 .
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.480
_refine_diff_density_min   -0.458
_refine_diff_density_rms    0.121
