 
data_07skc0011p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
adipic acid 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H22 N4 O6'
_chemical_formula_weight          318.34
 
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                    7.7814(3)
_cell_length_b                    22.3584(11)
_cell_length_c                    9.1957(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.329(3)
_cell_angle_gamma                 90.00
_cell_volume                      1556.77(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3364
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.13
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              680
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9859
_exptl_absorpt_correction_T_max   0.9956
_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             14674
_diffrn_reflns_av_R_equivalents   0.0880
_diffrn_reflns_av_sigmaI/netI     0.0856
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        29
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3521
_reflns_number_gt                 2194
_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)+(0.0127P)²+4.5713P] 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          3521
_refine_ls_number_parameters      201
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1552
_refine_ls_R_factor_gt            0.0934
_refine_ls_wR_factor_ref          0.1880
_refine_ls_wR_factor_gt           0.1574
_refine_ls_goodness_of_fit_ref    1.133
_refine_ls_restrained_S_all       1.133
_refine_ls_shift/su_max           0.024
_refine_ls_shift/su_mean          0.003
 
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 0.9036(5) -0.02891(17) 1.2022(4) 0.0233(8) Uani 1 1 d . . .
C2 C 0.8931(5) 0.03736(16) 1.1668(4) 0.0225(8) Uani 1 1 d . . .
H2A H 1.0122 0.0520 1.1633 0.027 Uiso 1 1 calc R . .
H2B H 0.8556 0.0590 1.2482 0.027 Uiso 1 1 calc R . .
C3 C 0.7651(5) 0.05173(16) 1.0190(4) 0.0219(8) Uani 1 1 d . . .
H3A H 0.6452 0.0385 1.0238 0.026 Uiso 1 1 calc R . .
H3B H 0.8001 0.0290 0.9380 0.026 Uiso 1 1 calc R . .
C4 C 0.7598(5) 0.11830(15) 0.9811(4) 0.0191(8) Uani 1 1 d . . .
H4A H 0.7294 0.1413 1.0636 0.023 Uiso 1 1 calc R . .
H4B H 0.8782 0.1313 0.9713 0.023 Uiso 1 1 calc R . .
C5 C 0.6252(5) 0.13175(16) 0.8364(4) 0.0238(9) Uani 1 1 d . . .
H5A H 0.6606 0.1107 0.7533 0.029 Uiso 1 1 calc R . .
H5B H 0.5089 0.1158 0.8440 0.029 Uiso 1 1 calc R . .
C6 C 0.6066(5) 0.19715(17) 0.8003(4) 0.0220(8) Uani 1 1 d . . .
O1A O 1.0315(4) -0.04297(12) 1.3160(3) 0.0333(7) Uani 1 1 d . . .
H1 H 1.0327 -0.0802 1.3288 0.050 Uiso 1 1 calc R . .
O1B O 0.8027(4) -0.06541(11) 1.1299(3) 0.0321(7) Uani 1 1 d . . .
O6A O 0.6751(3) 0.23670(11) 0.8838(3) 0.0264(7) Uani 1 1 d . . .
O6B O 0.5035(4) 0.20743(12) 0.6662(3) 0.0293(7) Uani 1 1 d . . .
H6 H 0.4930 0.2445 0.6517 0.044 Uiso 1 1 calc R . .
C22 C 0.4539(5) 0.36287(16) 0.7029(4) 0.0227(8) Uani 1 1 d . . .
C24 C 0.5462(6) 0.41567(17) 0.9224(5) 0.0333(10) Uani 1 1 d . . .
H24A H 0.6609 0.4325 0.9762 0.040 Uiso 1 1 calc R . .
H24B H 0.4736 0.4065 0.9949 0.040 Uiso 1 1 calc R . .
C25 C 0.4493(6) 0.45812(17) 0.7992(5) 0.0304(10) Uani 1 1 d . . .
H25A H 0.3595 0.4823 0.8333 0.036 Uiso 1 1 calc R . .
H25B H 0.5328 0.4852 0.7650 0.036 Uiso 1 1 calc R . .
N21 N 0.3677(4) 0.41618(14) 0.6821(4) 0.0276(8) Uani 1 1 d . . .
H21 H 0.2760 0.4242 0.6088 0.033 Uiso 1 1 calc R . .
N23 N 0.5702(4) 0.36318(14) 0.8357(4) 0.0269(8) Uani 1 1 d . . .
H23 H 0.6503 0.3353 0.8664 0.032 Uiso 1 1 calc R . .
O22 O 0.4255(3) 0.32078(11) 0.6112(3) 0.0237(6) Uani 1 1 d . . .
C32 C 0.0063(5) 0.69651(17) 0.8064(4) 0.0231(8) Uani 1 1 d . . .
C34 C -0.0361(5) 0.79529(17) 0.7328(5) 0.0268(9) Uani 1 1 d . . .
H34A H 0.0504 0.8112 0.6788 0.032 Uiso 1 1 calc R . .
H34B H -0.0913 0.8290 0.7750 0.032 Uiso 1 1 calc R . .
C35 C -0.1757(5) 0.75594(16) 0.6307(5) 0.0244(9) Uani 1 1 d . . .
H35A H -0.2945 0.7626 0.6494 0.029 Uiso 1 1 calc R . .
H35B H -0.1797 0.7635 0.5239 0.029 Uiso 1 1 calc R . .
N31 N -0.1118(4) 0.69607(14) 0.6746(4) 0.0280(8) Uani 1 1 d . . .
H31 H -0.1461 0.6637 0.6215 0.034 Uiso 1 1 calc R . .
N33 N 0.0458(4) 0.75303(13) 0.8483(4) 0.0256(8) Uani 1 1 d . . .
H33 H 0.1132 0.7634 0.9352 0.031 Uiso 1 1 calc R . .
O32 O 0.0728(4) 0.65166(11) 0.8816(3) 0.0307(7) 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 1.218(4) . ?
C1 O1A 1.305(4) . ?
C1 C2 1.515(5) . ?
C2 C3 1.523(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.499(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O6A 1.211(4) . ?
C6 O6B 1.328(4) . ?
O1A H1 0.8400 . ?
O6B H6 0.8400 . ?
C22 O22 1.249(4) . ?
C22 N23 1.342(5) . ?
C22 N21 1.360(5) . ?
C24 N23 1.454(5) . ?
C24 C25 1.536(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.260(5) . ?
C32 N33 1.336(5) . ?
C32 N31 1.342(5) . ?
C34 N33 1.454(5) . ?
C34 C35 1.538(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N31 1.452(5) . ?
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
O1B C1 O1A 123.5(3) . . ?
O1B C1 C2 122.8(3) . . ?
O1A C1 C2 113.6(3) . . ?
C1 C2 C3 112.9(3) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 112.8(3) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.7(3) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 113.5(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O6A C6 O6B 123.1(3) . . ?
O6A C6 C5 124.5(3) . . ?
O6B C6 C5 112.4(3) . . ?
C1 O1A H1 109.5 . . ?
C6 O6B H6 109.5 . . ?
O22 C22 N23 126.6(3) . . ?
O22 C22 N21 124.1(3) . . ?
N23 C22 N21 109.3(3) . . ?
N23 C24 C25 101.4(3) . . ?
N23 C24 H24A 111.5 . . ?
C25 C24 H24A 111.5 . . ?
N23 C24 H24B 111.5 . . ?
C25 C24 H24B 111.5 . . ?
H24A C24 H24B 109.3 . . ?
N21 C25 C24 101.7(3) . . ?
N21 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N21 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C22 N21 C25 110.1(3) . . ?
C22 N21 H21 125.0 . . ?
C25 N21 H21 125.0 . . ?
C22 N23 C24 111.0(3) . . ?
C22 N23 H23 124.5 . . ?
C24 N23 H23 124.5 . . ?
O32 C32 N33 123.8(3) . . ?
O32 C32 N31 126.8(3) . . ?
N33 C32 N31 109.3(3) . . ?
N33 C34 C35 101.7(3) . . ?
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 102.1(3) . . ?
N31 C35 H35A 111.4 . . ?
C34 C35 H35A 111.4 . . ?
N31 C35 H35B 111.4 . . ?
C34 C35 H35B 111.4 . . ?
H35A C35 H35B 109.2 . . ?
C32 N31 C35 111.3(3) . . ?
C32 N31 H31 124.3 . . ?
C35 N31 H31 124.3 . . ?
C32 N33 C34 111.8(3) . . ?
C32 N33 H33 124.1 . . ?
C34 N33 H33 124.1 . . ?
 
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
O6B H6 O22  0.84 1.80 2.628(4) 168.9 .
N23 H23 O6A  0.88 2.22 2.948(4) 140.4 .
O1A H1 O32  0.84 1.68 2.507(4) 168.2 4_666
N21 H21 O1B  0.88 2.15 2.900(4) 142.6 2_656
N31 H31 O1B  0.88 2.24 3.003(4) 145.4 4_465
N33 H33 O6A  0.88 2.05 2.894(4) 159.1 3_667
 
_diffrn_measured_fraction_theta_max    0.989
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.989
_refine_diff_density_max    0.551
_refine_diff_density_min   -0.373
_refine_diff_density_rms    0.083
