 
data_ssf1338
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
succinic acid & 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H18 N4 O6'
_chemical_formula_weight          290.28
 
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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.5097(15)
_cell_length_b                    9.529(2)
_cell_length_c                    13.030(3)
_cell_angle_alpha                 104.839(3)
_cell_angle_beta                  91.938(3)
_cell_angle_gamma                 95.093(3)
_cell_volume                      657.5(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     913
_cell_measurement_theta_min       3.61
_cell_measurement_theta_max       29.25

 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.466
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              308
_exptl_absorpt_coefficient_mu     0.122
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.9856
_exptl_absorpt_correction_T_max   0.9952
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.6905
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator   'silicon 111'
_diffrn_measurement_device_type   'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method        'fine-slice ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         5
_diffrn_reflns_number             5694
_diffrn_reflns_av_R_equivalents   0.0277
_diffrn_reflns_av_sigmaI/netI     0.0424
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          26.64
_reflns_number_total              2909
_reflns_number_gt                 2337
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_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)+(0.0846P)²+0.3023P] 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          2909
_refine_ls_number_parameters      183
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0626
_refine_ls_R_factor_gt            0.0507
_refine_ls_wR_factor_ref          0.1486
_refine_ls_wR_factor_gt           0.1386
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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 0.0960(3) 0.32238(17) 0.90949(13) 0.0175(3) Uani 1 1 d . . .
C2 C -0.0540(3) 0.42133(17) 0.98461(13) 0.0184(4) Uani 1 1 d . . .
H2A H -0.0702 0.3868 1.0498 0.022 Uiso 1 1 calc R . .
H2B H -0.2197 0.4153 0.9510 0.022 Uiso 1 1 calc R . .
O1A O 0.0212(2) 0.18438(13) 0.89571(10) 0.0232(3) Uani 1 1 d . . .
H1 H 0.1091 0.1331 0.8529 0.035 Uiso 1 1 calc R . .
O1B O 0.2693(2) 0.36534(13) 0.86537(10) 0.0252(3) Uani 1 1 d . . .
C22 C 0.5970(3) -0.01663(18) 0.29276(13) 0.0190(3) Uani 1 1 d . . .
C24 C 0.2806(3) 0.04334(19) 0.40366(14) 0.0214(4) Uani 1 1 d . . .
H24A H 0.1433 0.0823 0.3727 0.026 Uiso 1 1 calc R . .
H24B H 0.2789 0.0735 0.4822 0.026 Uiso 1 1 calc R . .
C25 C 0.2681(3) -0.12373(19) 0.36197(14) 0.0225(4) Uani 1 1 d . . .
H25A H 0.3026 -0.1700 0.4201 0.027 Uiso 1 1 calc R . .
H25B H 0.1063 -0.1653 0.3266 0.027 Uiso 1 1 calc R . .
N21 N 0.4589(3) -0.14198(17) 0.28625(13) 0.0280(4) Uani 1 1 d . . .
H21 H 0.4809 -0.2256 0.2415 0.034 Uiso 1 1 calc R . .
N23 N 0.5132(3) 0.09167(16) 0.36767(12) 0.0225(3) Uani 1 1 d . . .
H23 H 0.5894 0.1799 0.3916 0.027 Uiso 1 1 calc R . .
O22 O 0.7753(2) 0.00200(13) 0.23943(10) 0.0236(3) Uani 1 1 d . . .
C31 C 0.2363(3) 0.50094(17) 0.59371(13) 0.0178(3) Uani 1 1 d . . .
C32 C 0.4099(3) 0.44165(17) 0.51072(13) 0.0185(3) Uani 1 1 d . . .
H32A H 0.3150 0.3904 0.4437 0.022 Uiso 1 1 calc R . .
H32B H 0.5009 0.3693 0.5343 0.022 Uiso 1 1 calc R . .
O31A O 0.0674(3) 0.40081(14) 0.60433(11) 0.0299(3) Uani 1 1 d . . .
H31 H -0.0205 0.4369 0.6538 0.045 Uiso 1 1 calc R . .
O31B O 0.2497(2) 0.62819(13) 0.64550(10) 0.0238(3) Uani 1 1 d . . .
C42 C -0.7204(3) 0.39826(18) 1.20842(13) 0.0182(3) Uani 1 1 d . . .
C44 C -0.5363(3) 0.21210(19) 1.09930(14) 0.0210(4) Uani 1 1 d . . .
H44A H -0.3892 0.1899 1.1355 0.025 Uiso 1 1 calc R . .
H44B H -0.5274 0.1751 1.0214 0.025 Uiso 1 1 calc R . .
C45 C -0.7712(3) 0.14809(18) 1.13788(13) 0.0212(4) Uani 1 1 d . . .
H45A H -0.9016 0.1175 1.0802 0.025 Uiso 1 1 calc R . .
H45B H -0.7416 0.0640 1.1665 0.025 Uiso 1 1 calc R . .
N41 N -0.8318(3) 0.27267(16) 1.22157(11) 0.0211(3) Uani 1 1 d . . .
H41 H -0.9275 0.2665 1.2733 0.025 Uiso 1 1 calc R . .
N43 N -0.5639(3) 0.36760(15) 1.12953(11) 0.0199(3) Uani 1 1 d . . .
H43 H -0.4897 0.4324 1.1007 0.024 Uiso 1 1 calc R . .
O42 O -0.7538(2) 0.52470(13) 1.25851(10) 0.0234(3) Uani 1 1 d . . .
 
 
_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 O1B 1.224(2) . ?
C1 O1A 1.307(2) . ?
C1 C2 1.500(2) . ?
C2 C2 1.510(3) 2_567 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O1A H1 0.8400 . ?
C22 O22 1.248(2) . ?
C22 N21 1.340(2) . ?
C22 N23 1.353(2) . ?
C24 N23 1.456(2) . ?
C24 C25 1.539(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31B 1.2218(19) . ?
C31 O31A 1.309(2) . ?
C31 C32 1.502(2) . ?
C32 C32 1.511(3) 2_666 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
O31A H31 0.8400 . ?
C42 O42 1.248(2) . ?
C42 N41 1.349(2) . ?
C42 N43 1.355(2) . ?
C44 N43 1.456(2) . ?
C44 C45 1.536(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N41 1.463(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N41 H41 0.8800 . ?
N43 H43 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
O1B C1 O1A 123.33(14) . . ?
O1B C1 C2 124.02(15) . . ?
O1A C1 C2 112.65(13) . . ?
C1 C2 C2 113.23(17) . 2_567 ?
C1 C2 H2A 108.9 . . ?
C2 C2 H2A 108.9 2_567 . ?
C1 C2 H2B 108.9 . . ?
C2 C2 H2B 108.9 2_567 . ?
H2A C2 H2B 107.7 . . ?
C1 O1A H1 109.5 . . ?
O22 C22 N21 127.08(16) . . ?
O22 C22 N23 123.64(16) . . ?
N21 C22 N23 109.28(15) . . ?
N23 C24 C25 102.56(13) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 102.31(14) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 112.17(14) . . ?
C22 N21 H21 123.9 . . ?
C25 N21 H21 123.9 . . ?
C22 N23 C24 111.24(14) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?
O31B C31 O31A 123.53(15) . . ?
O31B C31 C32 124.09(15) . . ?
O31A C31 C32 112.38(13) . . ?
C31 C32 C32 113.14(17) . 2_666 ?
C31 C32 H32A 109.0 . . ?
C32 C32 H32A 109.0 2_666 . ?
C31 C32 H32B 109.0 . . ?
C32 C32 H32B 109.0 2_666 . ?
H32A C32 H32B 107.8 . . ?
C31 O31A H31 109.5 . . ?
O42 C42 N41 126.84(15) . . ?
O42 C42 N43 123.71(16) . . ?
N41 C42 N43 109.44(14) . . ?
N43 C44 C45 101.78(13) . . ?
N43 C44 H44A 111.4 . . ?
C45 C44 H44A 111.4 . . ?
N43 C44 H44B 111.4 . . ?
C45 C44 H44B 111.4 . . ?
H44A C44 H44B 109.3 . . ?
N41 C45 C44 101.42(13) . . ?
N41 C45 H45A 111.5 . . ?
C44 C45 H45A 111.5 . . ?
N41 C45 H45B 111.5 . . ?
C44 C45 H45B 111.5 . . ?
H45A C45 H45B 109.3 . . ?
C42 N41 C45 110.55(14) . . ?
C42 N41 H41 124.7 . . ?
C45 N41 H41 124.7 . . ?
C42 N43 C44 110.28(14) . . ?
C42 N43 H43 124.9 . . ?
C44 N43 H43 124.9 . . ?
 
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
O1A H1 O22  0.84 1.71 2.5293(17) 165.6 2_656
N21 H21 O1B  0.88 2.26 3.047(2) 148.8 2_656
O31A H31 O42  0.84 1.72 2.5418(17) 166.6 2_467
N41 H41 O31B  0.88 2.28 3.0023(19) 139.9 2_467
N23 H23 O31B  0.88 2.13 2.914(2) 147.3 2_666
N43 H43 O1B  0.88 2.12 2.879(2) 144.0 2_567
 
_diffrn_measured_fraction_theta_max    0.965
_diffrn_reflns_theta_full              26.64
_diffrn_measured_fraction_theta_full   0.965
_refine_diff_density_max    0.454
_refine_diff_density_min   -0.475
_refine_diff_density_rms    0.058
