 
data_06skc0012p212121
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
2-pyrrolidinone-5-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C5 H7 N O3'
_chemical_formula_weight          129.12
 
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            orthorhombic
_symmetry_space_group_name_H-M    P212121
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    8.1972(10)
_cell_length_b                    14.340(2)
_cell_length_c                    14.6661(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1724.0(4)
_cell_formula_units_Z             12
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2566
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       23.26
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.492
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              816
_exptl_absorpt_coefficient_mu     0.125
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9731
_exptl_absorpt_correction_T_max   0.9926
_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             23141
_diffrn_reflns_av_R_equivalents   0.1562
_diffrn_reflns_av_sigmaI/netI     0.0869
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.12
_diffrn_reflns_theta_max          23.37
_reflns_number_total              2495
_reflns_number_gt                 1581
_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)+(0.0534P)²+0.0000P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0(2)
_refine_ls_number_reflns          2495
_refine_ls_number_parameters      247
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1088
_refine_ls_R_factor_gt            0.0518
_refine_ls_wR_factor_ref          0.1118
_refine_ls_wR_factor_gt           0.0942
_refine_ls_goodness_of_fit_ref    1.012
_refine_ls_restrained_S_all       1.012
_refine_ls_shift/su_max           0.001
_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
C2 C -0.1812(6) 0.2133(3) 0.0329(3) 0.0385(12) Uani 1 1 d . . .
C3 C -0.2817(6) 0.1266(3) 0.0214(3) 0.0400(13) Uani 1 1 d . . .
H3A H -0.2261 0.0813 -0.0190 0.048 Uiso 1 1 calc R . .
H3B H -0.3902 0.1415 -0.0044 0.048 Uiso 1 1 calc R . .
C4 C -0.2970(6) 0.0884(3) 0.1184(3) 0.0422(13) Uani 1 1 d . . .
H4A H -0.2976 0.0194 0.1183 0.051 Uiso 1 1 calc R . .
H4B H -0.3979 0.1112 0.1480 0.051 Uiso 1 1 calc R . .
C5 C -0.1449(5) 0.1262(3) 0.1670(3) 0.0405(13) Uani 1 1 d . . .
H5 H -0.0526 0.0811 0.1605 0.049 Uiso 1 1 calc R . .
C6 C -0.1747(5) 0.1469(4) 0.2670(3) 0.0392(12) Uani 1 1 d . . .
N1 N -0.1108(5) 0.2104(3) 0.1150(2) 0.0416(11) Uani 1 1 d . . .
H1 H -0.0488 0.2557 0.1359 0.050 Uiso 1 1 calc R . .
O2 O -0.1615(4) 0.2784(2) -0.0219(2) 0.0475(9) Uani 1 1 d . . .
O6A O -0.2011(4) 0.0693(2) 0.31287(18) 0.0439(8) Uani 1 1 d . . .
H6A H -0.2123 0.0818 0.3685 0.066 Uiso 1 1 calc R . .
O6B O -0.1727(4) 0.2239(2) 0.2995(2) 0.0492(9) Uani 1 1 d . . .
C22 C 0.2288(5) 0.3428(3) 0.4687(3) 0.0365(12) Uani 1 1 d . . .
C23 C 0.3654(5) 0.2732(3) 0.4788(3) 0.0419(13) Uani 1 1 d . . .
H23A H 0.3349 0.2231 0.5219 0.050 Uiso 1 1 calc R . .
H23B H 0.4660 0.3040 0.5009 0.050 Uiso 1 1 calc R . .
C24 C 0.3899(5) 0.2340(3) 0.3822(3) 0.0381(13) Uani 1 1 d . . .
H24A H 0.4753 0.2690 0.3488 0.046 Uiso 1 1 calc R . .
H24B H 0.4198 0.1672 0.3839 0.046 Uiso 1 1 calc R . .
C25 C 0.2220(6) 0.2483(3) 0.3386(3) 0.0393(12) Uani 1 1 d . . .
H25 H 0.1527 0.1924 0.3513 0.047 Uiso 1 1 calc R . .
C26 C 0.2243(6) 0.2660(4) 0.2378(3) 0.0394(12) Uani 1 1 d . . .
N21 N 0.1569(5) 0.3277(2) 0.3884(2) 0.0400(10) Uani 1 1 d . . .
H21 H 0.0771 0.3627 0.3674 0.048 Uiso 1 1 calc R . .
O22 O 0.1877(4) 0.4034(2) 0.5244(2) 0.0405(8) Uani 1 1 d . . .
O26A O 0.3019(4) 0.1991(2) 0.1941(2) 0.0545(9) Uani 1 1 d . . .
H26A H 0.3001 0.2101 0.1378 0.082 Uiso 1 1 calc R . .
O26B O 0.1573(3) 0.3313(2) 0.2010(2) 0.0427(8) Uani 1 1 d . . .
C32 C 0.3212(6) 0.0094(3) 0.9219(3) 0.0406(13) Uani 1 1 d . . .
C33 C 0.1421(5) 0.0285(3) 0.9343(3) 0.0405(12) Uani 1 1 d . . .
H33A H 0.1245 0.0847 0.9723 0.049 Uiso 1 1 calc R . .
H33B H 0.0865 -0.0252 0.9632 0.049 Uiso 1 1 calc R . .
C34 C 0.0802(5) 0.0440(3) 0.8368(3) 0.0431(12) Uani 1 1 d . . .
H34A H -0.0110 0.0892 0.8356 0.052 Uiso 1 1 calc R . .
H34B H 0.0438 -0.0153 0.8089 0.052 Uiso 1 1 calc R . .
C35 C 0.2309(5) 0.0829(3) 0.7877(3) 0.0385(12) Uani 1 1 d . . .
H35 H 0.2343 0.1521 0.7964 0.046 Uiso 1 1 calc R . .
C36 C 0.2468(6) 0.0614(3) 0.6872(3) 0.0386(12) Uani 1 1 d . . .
N31 N 0.3631(4) 0.0410(2) 0.8394(2) 0.0400(10) Uani 1 1 d . . .
H31 H 0.4631 0.0367 0.8181 0.048 Uiso 1 1 calc R . .
O32 O 0.4155(4) -0.0288(2) 0.9754(2) 0.0458(9) Uani 1 1 d . . .
O36A O 0.1035(4) 0.0650(2) 0.64571(19) 0.0476(9) Uani 1 1 d . . .
H36A H 0.1163 0.0560 0.5896 0.071 Uiso 1 1 calc R . .
O36B O 0.3750(4) 0.0467(2) 0.64987(19) 0.0434(9) 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
C2 O2 1.243(5) . ?
C2 N1 1.335(5) . ?
C2 C3 1.501(6) . ?
C3 C4 1.529(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.535(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.456(5) . ?
C5 C6 1.516(6) . ?
C5 H5 1.0000 . ?
C6 O6B 1.202(5) . ?
C6 O6A 1.318(5) . ?
N1 H1 0.8800 . ?
O6A H6A 0.8400 . ?
C22 O22 1.239(5) . ?
C22 N21 1.335(5) . ?
C22 C23 1.507(6) . ?
C23 C24 1.537(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.531(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.454(5) . ?
C25 C26 1.501(5) . ?
C25 H25 1.0000 . ?
C26 O26B 1.213(5) . ?
C26 O26A 1.317(5) . ?
N21 H21 0.8800 . ?
O26A H26A 0.8400 . ?
C32 O32 1.230(5) . ?
C32 N31 1.337(5) . ?
C32 C33 1.505(6) . ?
C33 C34 1.533(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.535(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N31 1.452(5) . ?
C35 C36 1.511(6) . ?
C35 H35 1.0000 . ?
C36 O36B 1.204(5) . ?
C36 O36A 1.325(5) . ?
N31 H31 0.8800 . ?
O36A H36A 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
O2 C2 N1 123.4(4) . . ?
O2 C2 C3 128.4(4) . . ?
N1 C2 C3 108.2(4) . . ?
C2 C3 C4 103.7(3) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 103.8(4) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N1 C5 C6 112.1(4) . . ?
N1 C5 C4 101.9(3) . . ?
C6 C5 C4 112.8(4) . . ?
N1 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
O6B C6 O6A 125.1(4) . . ?
O6B C6 C5 124.1(4) . . ?
O6A C6 C5 110.8(4) . . ?
C2 N1 C5 114.5(4) . . ?
C2 N1 H1 122.7 . . ?
C5 N1 H1 122.7 . . ?
C6 O6A H6A 109.5 . . ?
O22 C22 N21 125.1(4) . . ?
O22 C22 C23 127.0(4) . . ?
N21 C22 C23 107.9(4) . . ?
C22 C23 C24 104.4(3) . . ?
C22 C23 H23A 110.9 . . ?
C24 C23 H23A 110.9 . . ?
C22 C23 H23B 110.9 . . ?
C24 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
C25 C24 C23 102.6(3) . . ?
C25 C24 H24A 111.2 . . ?
C23 C24 H24A 111.2 . . ?
C25 C24 H24B 111.2 . . ?
C23 C24 H24B 111.2 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C26 111.5(4) . . ?
N21 C25 C24 103.0(4) . . ?
C26 C25 C24 114.9(4) . . ?
N21 C25 H25 109.0 . . ?
C26 C25 H25 109.0 . . ?
C24 C25 H25 109.0 . . ?
O26B C26 O26A 124.3(4) . . ?
O26B C26 C25 124.3(5) . . ?
O26A C26 C25 111.3(5) . . ?
C22 N21 C25 114.1(4) . . ?
C22 N21 H21 123.0 . . ?
C25 N21 H21 123.0 . . ?
C26 O26A H26A 109.5 . . ?
O32 C32 N31 124.5(4) . . ?
O32 C32 C33 128.1(4) . . ?
N31 C32 C33 107.4(4) . . ?
C32 C33 C34 103.6(3) . . ?
C32 C33 H33A 111.0 . . ?
C34 C33 H33A 111.0 . . ?
C32 C33 H33B 111.0 . . ?
C34 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?
C33 C34 C35 102.9(3) . . ?
C33 C34 H34A 111.2 . . ?
C35 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
C35 C34 H34B 111.2 . . ?
H34A C34 H34B 109.1 . . ?
N31 C35 C36 111.1(4) . . ?
N31 C35 C34 101.8(3) . . ?
C36 C35 C34 116.9(4) . . ?
N31 C35 H35 108.9 . . ?
C36 C35 H35 108.9 . . ?
C34 C35 H35 108.9 . . ?
O36B C36 O36A 124.9(4) . . ?
O36B C36 C35 123.7(4) . . ?
O36A C36 C35 111.4(4) . . ?
C32 N31 C35 114.9(4) . . ?
C32 N31 H31 122.5 . . ?
C35 N31 H31 122.5 . . ?
C36 O36A H36A 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
N1 H1 O26B  0.88 2.22 3.070(5) 161.5 .
O6A H6A O22  0.84 1.79 2.585(4) 158.5 4_456
N21 H21 O36B  0.88 2.12 2.983(5) 166.4 4_456
O26A H26A O2  0.84 1.74 2.563(4) 167.4 4
O36A H36A O32  0.84 1.74 2.556(4) 163.6 2_554
N31 H31 O26B  0.88 2.49 3.086(5) 125.7 4_556
N31 H31 O6A  0.88 2.47 3.214(5) 142.0 2
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              23.37
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.218
_refine_diff_density_min   -0.268
_refine_diff_density_rms    0.056
