 
data_07skc0026p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Maleic acid and 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H14 N2 O9'
_chemical_formula_weight          318.24
 
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                    31.3779(13)
_cell_length_b                    12.3307(6)
_cell_length_c                    7.1600(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.968(2)
_cell_angle_gamma                 90.00
_cell_volume                      2766.6(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5433
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.528
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1328
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9840
_exptl_absorpt_correction_T_max   0.9973
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_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 APEX II 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             17424
_diffrn_reflns_av_R_equivalents   0.0788
_diffrn_reflns_av_sigmaI/netI     0.0819
_diffrn_reflns_limit_h_min        -37
_diffrn_reflns_limit_h_max        37
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          25.00
_reflns_number_total              4829
_reflns_number_gt                 2884
_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.

 Due to the small size and weakly diffracting nature of the crystals, data
 were only included out to 25deg.

 H54 was found on the difference map in a nearly central position between
 O54B and O42; therefore although it was attached to O54B in keeping with
 the protonation of the rest of the structure, its position cannot be
 conclusively determined with this data alone.
;
 
_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+17.7474P] 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          4829
_refine_ls_number_parameters      405
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1648
_refine_ls_R_factor_gt            0.0990
_refine_ls_wR_factor_ref          0.2044
_refine_ls_wR_factor_gt           0.1681
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_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 0.37280(18) 0.1485(5) -0.0507(8) 0.0217(13) Uani 1 1 d . . .
C2 C 0.33647(17) 0.0987(5) 0.0388(8) 0.0221(13) Uani 1 1 d . . .
H2 H 0.3363 0.0217 0.0420 0.026 Uiso 1 1 calc R . .
C3 C 0.30351(17) 0.1472(5) 0.1164(8) 0.0214(13) Uani 1 1 d . . .
H3 H 0.2835 0.0986 0.1663 0.026 Uiso 1 1 calc R . .
C4 C 0.29271(17) 0.2638(5) 0.1381(8) 0.0203(13) Uani 1 1 d . . .
O1A O 0.39903(12) 0.0807(3) -0.1142(6) 0.0278(10) Uani 1 1 d . . .
H1 H 0.4195 0.1142 -0.1584 0.042 Uiso 1 1 calc R . .
O1B O 0.37738(12) 0.2505(3) -0.0630(6) 0.0263(9) Uani 1 1 d . . .
O4A O 0.31687(12) 0.3397(3) 0.0781(6) 0.0240(9) Uani 1 1 d . . .
H4 H 0.3379 0.3119 0.0282 0.036 Uiso 1 1 calc R . .
O4B O 0.25948(12) 0.2862(3) 0.2171(5) 0.0244(9) Uani 1 1 d . . .
C22 C 0.52110(17) 0.7718(4) 0.2592(8) 0.0204(13) Uani 1 1 d . . .
C24 C 0.47730(17) 0.6282(5) 0.3165(9) 0.0259(14) Uani 1 1 d . . .
H24A H 0.4521 0.6031 0.2395 0.031 Uiso 1 1 calc R . .
H24B H 0.4746 0.6042 0.4473 0.031 Uiso 1 1 calc R . .
C25 C 0.51906(18) 0.5866(5) 0.2378(9) 0.0272(14) Uani 1 1 d . . .
H25A H 0.5332 0.5326 0.3223 0.033 Uiso 1 1 calc R . .
H25B H 0.5139 0.5540 0.1123 0.033 Uiso 1 1 calc R . .
N21 N 0.54423(15) 0.6852(4) 0.2286(7) 0.0261(12) Uani 1 1 d . . .
H21 H 0.5715 0.6868 0.2054 0.031 Uiso 1 1 calc R . .
N23 N 0.48202(15) 0.7452(4) 0.3055(7) 0.0280(12) Uani 1 1 d . . .
H23 H 0.4617 0.7922 0.3268 0.034 Uiso 1 1 calc R . .
O22 O 0.53326(12) 0.8711(3) 0.2446(6) 0.0267(10) Uani 1 1 d . . .
C31 C 0.19861(19) 0.4920(5) 0.3574(8) 0.0227(13) Uani 1 1 d . . .
C32 C 0.18501(17) 0.6074(5) 0.3783(8) 0.0231(13) Uani 1 1 d . . .
H32 H 0.2034 0.6606 0.3304 0.028 Uiso 1 1 calc R . .
C33 C 0.15027(18) 0.6446(5) 0.4560(8) 0.0250(14) Uani 1 1 d . . .
H33 H 0.1478 0.7214 0.4516 0.030 Uiso 1 1 calc R . .
C34 C 0.11459(17) 0.5911(5) 0.5478(8) 0.0228(13) Uani 1 1 d . . .
O31A O 0.17860(12) 0.4129(3) 0.4065(6) 0.0252(10) Uani 1 1 d . . .
O31B O 0.23499(12) 0.4849(3) 0.2747(6) 0.0265(10) Uani 1 1 d . . .
H31 H 0.2443 0.4212 0.2836 0.040 Uiso 1 1 calc R . .
O34A O 0.11211(12) 0.4837(3) 0.5535(6) 0.0268(10) Uani 1 1 d . . .
H34 H 0.1338 0.4567 0.5073 0.040 Uiso 1 1 calc R . .
O34B O 0.08721(12) 0.6459(3) 0.6182(6) 0.0297(10) Uani 1 1 d . . .
C42 C 0.01642(17) 0.4877(5) 1.2180(7) 0.0204(13) Uani 1 1 d . . .
C44 C 0.01789(17) 0.6740(5) 1.2355(8) 0.0240(13) Uani 1 1 d . . .
H44A H 0.0128 0.7153 1.1179 0.029 Uiso 1 1 calc R . .
H44B H 0.0334 0.7205 1.3289 0.029 Uiso 1 1 calc R . .
C45 C -0.02461(18) 0.6319(5) 1.3103(8) 0.0237(13) Uani 1 1 d . . .
H45A H -0.0261 0.6460 1.4459 0.028 Uiso 1 1 calc R . .
H45B H -0.0496 0.6653 1.2427 0.028 Uiso 1 1 calc R . .
N41 N -0.02207(15) 0.5154(4) 1.2713(7) 0.0269(12) Uani 1 1 d . . .
H41 H -0.0433 0.4696 1.2818 0.032 Uiso 1 1 calc R . .
N43 N 0.04119(14) 0.5741(4) 1.2036(7) 0.0214(11) Uani 1 1 d . . .
H43 H 0.0683 0.5714 1.1779 0.026 Uiso 1 1 calc R . .
O42 O 0.02677(12) 0.3892(3) 1.1872(6) 0.0248(10) Uani 1 1 d . . .
C51 C 0.20532(17) 0.5167(5) 0.8440(8) 0.0210(13) Uani 1 1 d . . .
C52 C 0.19495(19) 0.4004(5) 0.8719(8) 0.0242(14) Uani 1 1 d . . .
H52 H 0.2156 0.3509 0.8298 0.029 Uiso 1 1 calc R . .
C53 C 0.16143(18) 0.3541(5) 0.9464(8) 0.0232(13) Uani 1 1 d . . .
H53 H 0.1622 0.2771 0.9500 0.028 Uiso 1 1 calc R . .
C54 C 0.12293(18) 0.4036(5) 1.0250(8) 0.0225(13) Uani 1 1 d . . .
O51A O 0.23829(12) 0.5396(3) 0.7677(6) 0.0263(10) Uani 1 1 d . . .
O51B O 0.17965(12) 0.5938(3) 0.8969(6) 0.0221(9) Uani 1 1 d . . .
H51 H 0.1576 0.5658 0.9381 0.033 Uiso 1 1 calc R . .
O54A O 0.11834(12) 0.5054(3) 1.0335(6) 0.0243(9) Uani 1 1 d . . .
O54B O 0.09614(12) 0.3365(3) 1.0819(6) 0.0291(10) Uani 1 1 d . . .
H54 H 0.0735 0.3692 1.1052 0.044 Uiso 1 1 calc R . .
C61 C 0.38551(18) 0.8448(5) 0.4555(8) 0.0234(14) Uani 1 1 d . . .
C62 C 0.34773(18) 0.8988(5) 0.5325(8) 0.0252(14) Uani 1 1 d . . .
H62 H 0.3492 0.9757 0.5314 0.030 Uiso 1 1 calc R . .
C63 C 0.31241(18) 0.8603(5) 0.6023(8) 0.0228(13) Uani 1 1 d . . .
H63 H 0.2925 0.9133 0.6390 0.027 Uiso 1 1 calc R . .
C64 C 0.29968(17) 0.7453(5) 0.6309(8) 0.0218(13) Uani 1 1 d . . .
O61A O 0.38847(13) 0.7382(3) 0.4493(7) 0.0344(11) Uani 1 1 d . . .
H61 H 0.3652 0.7105 0.4771 0.052 Uiso 1 1 calc R . .
O61B O 0.41391(14) 0.9014(4) 0.3985(6) 0.0369(11) Uani 1 1 d . . .
O64A O 0.32100(12) 0.6662(3) 0.5869(6) 0.0296(10) Uani 1 1 d . . .
O64B O 0.26279(12) 0.7368(3) 0.7053(6) 0.0259(10) Uani 1 1 d . . .
H64 H 0.2575 0.6712 0.7249 0.039 Uiso 1 1 calc R . .
 
 
_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 1.270(7) . ?
C1 O1A 1.273(7) . ?
C1 C2 1.471(8) . ?
C2 C3 1.340(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.487(8) . ?
C3 H3 0.9500 . ?
C4 O4B 1.243(6) . ?
C4 O4A 1.292(6) . ?
O1A H1 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.288(7) . ?
C22 N21 1.316(7) . ?
C22 N23 1.328(7) . ?
C24 N23 1.453(7) . ?
C24 C25 1.541(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.453(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31A 1.221(7) . ?
C31 O31B 1.316(7) . ?
C31 C32 1.495(8) . ?
C32 C33 1.331(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.482(8) . ?
C33 H33 0.9500 . ?
C34 O34B 1.222(7) . ?
C34 O34A 1.327(7) . ?
O31B H31 0.8400 . ?
O34A H34 0.8400 . ?
C42 O42 1.279(7) . ?
C42 N43 1.326(7) . ?
C42 N41 1.329(7) . ?
C44 N43 1.456(7) . ?
C44 C45 1.552(7) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N41 1.466(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N41 H41 0.8800 . ?
N43 H43 0.8800 . ?
C51 O51A 1.228(6) . ?
C51 O51B 1.314(6) . ?
C51 C52 1.487(8) . ?
C52 C53 1.332(8) . ?
C52 H52 0.9500 . ?
C53 C54 1.489(8) . ?
C53 H53 0.9500 . ?
C54 O54B 1.262(7) . ?
C54 O54A 1.265(7) . ?
O51B H51 0.8400 . ?
O54B H54 0.8400 . ?
C61 O61B 1.218(7) . ?
C61 O61A 1.320(7) . ?
C61 C62 1.490(8) . ?
C62 C63 1.327(8) . ?
C62 H62 0.9500 . ?
C63 C64 1.490(8) . ?
C63 H63 0.9500 . ?
C64 O64A 1.233(7) . ?
C64 O64B 1.303(6) . ?
O61A H61 0.8400 . ?
O64B H64 0.8400 . ?
 
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 123.2(5) . . ?
O1B C1 C2 122.5(5) . . ?
O1A C1 C2 114.3(5) . . ?
C3 C2 C1 128.8(5) . . ?
C3 C2 H2 115.6 . . ?
C1 C2 H2 115.6 . . ?
C2 C3 C4 131.3(5) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 H3 114.3 . . ?
O4B C4 O4A 120.7(5) . . ?
O4B C4 C3 117.7(5) . . ?
O4A C4 C3 121.6(5) . . ?
C1 O1A H1 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N21 126.1(5) . . ?
O22 C22 N23 122.4(5) . . ?
N21 C22 N23 111.5(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 102.3(5) . . ?
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 111.4(5) . . ?
C22 N21 H21 124.3 . . ?
C25 N21 H21 124.3 . . ?
C22 N23 C24 110.9(5) . . ?
C22 N23 H23 124.6 . . ?
C24 N23 H23 124.6 . . ?
O31A C31 O31B 123.2(5) . . ?
O31A C31 C32 125.3(5) . . ?
O31B C31 C32 111.5(5) . . ?
C33 C32 C31 127.9(5) . . ?
C33 C32 H32 116.0 . . ?
C31 C32 H32 116.0 . . ?
C32 C33 C34 133.3(6) . . ?
C32 C33 H33 113.4 . . ?
C34 C33 H33 113.4 . . ?
O34B C34 O34A 119.7(5) . . ?
O34B C34 C33 120.0(5) . . ?
O34A C34 C33 120.3(5) . . ?
C31 O31B H31 109.5 . . ?
C34 O34A H34 109.5 . . ?
O42 C42 N43 126.5(5) . . ?
O42 C42 N41 122.4(5) . . ?
N43 C42 N41 111.2(5) . . ?
N43 C44 C45 102.6(4) . . ?
N43 C44 H44A 111.2 . . ?
C45 C44 H44A 111.2 . . ?
N43 C44 H44B 111.2 . . ?
C45 C44 H44B 111.2 . . ?
H44A C44 H44B 109.2 . . ?
N41 C45 C44 101.9(4) . . ?
N41 C45 H45A 111.4 . . ?
C44 C45 H45A 111.4 . . ?
N41 C45 H45B 111.4 . . ?
C44 C45 H45B 111.4 . . ?
H45A C45 H45B 109.3 . . ?
C42 N41 C45 111.4(5) . . ?
C42 N41 H41 124.3 . . ?
C45 N41 H41 124.3 . . ?
C42 N43 C44 111.5(5) . . ?
C42 N43 H43 124.3 . . ?
C44 N43 H43 124.3 . . ?
O51A C51 O51B 120.3(5) . . ?
O51A C51 C52 118.5(5) . . ?
O51B C51 C52 121.1(5) . . ?
C53 C52 C51 130.5(5) . . ?
C53 C52 H52 114.7 . . ?
C51 C52 H52 114.7 . . ?
C52 C53 C54 130.5(5) . . ?
C52 C53 H53 114.8 . . ?
C54 C53 H53 114.8 . . ?
O54B C54 O54A 123.7(5) . . ?
O54B C54 C53 114.9(5) . . ?
O54A C54 C53 121.4(5) . . ?
C51 O51B H51 109.5 . . ?
C54 O54B H54 109.5 . . ?
O61B C61 O61A 120.3(5) . . ?
O61B C61 C62 118.6(5) . . ?
O61A C61 C62 121.1(5) . . ?
C63 C62 C61 132.5(6) . . ?
C63 C62 H62 113.7 . . ?
C61 C62 H62 113.7 . . ?
C62 C63 C64 128.8(5) . . ?
C62 C63 H63 115.6 . . ?
C64 C63 H63 115.6 . . ?
O64A C64 O64B 123.1(5) . . ?
O64A C64 C63 124.4(5) . . ?
O64B C64 C63 112.5(5) . . ?
C61 O61A H61 109.5 . . ?
C64 O64B H64 109.5 . . ?
 
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
O4A H4 O1B  0.84 1.62 2.456(5) 176.2 .
N23 H23 O61B  0.88 2.10 2.977(6) 175.8 .
N23 H23 O61A  0.88 2.59 3.162(6) 123.6 .
O31B H31 O4B  0.84 1.80 2.607(5) 160.0 .
O34A H34 O31A  0.84 1.70 2.540(5) 175.1 .
N43 H43 O54A  0.88 2.09 2.892(6) 151.3 .
O51B H51 O54A  0.84 1.62 2.457(5) 174.0 .
O54B H54 O42  0.84 1.63 2.429(5) 158.6 .
O61A H61 O64A  0.84 1.72 2.541(6) 166.0 .
O64B H64 O51A  0.84 1.76 2.596(6) 171.4 .
O1A H1 O22  0.84 1.64 2.438(5) 156.6 3_665
N21 H21 O1B  0.88 2.09 2.896(6) 151.3 3_665
N41 H41 O34B  0.88 2.13 2.987(6) 164.5 3_567
N41 H41 O34A  0.88 2.58 3.150(6) 123.5 3_567
 
_diffrn_measured_fraction_theta_max    0.988
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.988
_refine_diff_density_max    0.355
_refine_diff_density_min   -0.360
_refine_diff_density_rms    0.086
