 
data_04skc0010p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Pyrrolidinium DL-tartrate dihydrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H19 N O8'
_chemical_formula_weight          257.24
 
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            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.2670(45)
_cell_length_b                    7.3373(36)
_cell_length_c                    11.6052(51)
_cell_angle_alpha                 106.343(45)
_cell_angle_beta                  101.093(43)
_cell_angle_gamma                 93.796(58)
_cell_volume                      577.9(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2550
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.09
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.478
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              276
_exptl_absorpt_coefficient_mu     0.133
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9882
_exptl_absorpt_correction_T_max   0.9987
_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             10779
_diffrn_reflns_av_R_equivalents   0.0954
_diffrn_reflns_av_sigmaI/netI     0.1253
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2635
_reflns_number_gt                 1472
_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.

 The small size and weakly diffracting nature of the crystals has led to
 larger su's on the cell parameters.
;
 
_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)+(0.0371P)²+0.3956P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.044(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2635
_refine_ls_number_parameters      174
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.1574
_refine_ls_R_factor_gt            0.0808
_refine_ls_wR_factor_ref          0.1360
_refine_ls_wR_factor_gt           0.1105
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.068
_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
C1 C 0.4663(4) 0.4032(4) 0.6180(3) 0.0179(7) Uani 1 1 d . . .
C2 C 0.2586(4) 0.4186(4) 0.6175(3) 0.0181(7) Uani 1 1 d . . .
H2 H 0.2113 0.4938 0.5608 0.022 Uiso 1 1 calc R . .
C3 C 0.2396(4) 0.5278(4) 0.7460(3) 0.0203(7) Uani 1 1 d . . .
H3 H 0.2899 0.6652 0.7630 0.024 Uiso 1 1 calc R . .
C4 C 0.0347(4) 0.5176(4) 0.7556(3) 0.0193(7) Uani 1 1 d . . .
O1A O 0.5169(2) 0.2408(3) 0.58432(18) 0.0211(5) Uani 1 1 d . . .
O1B O 0.5758(2) 0.5599(3) 0.65299(18) 0.0201(5) Uani 1 1 d . . .
O2 O 0.1461(2) 0.2382(3) 0.57598(19) 0.0240(5) Uani 1 1 d . . .
H2O H 0.2161 0.1518 0.5776 0.036 Uiso 1 1 calc R . .
O3 O 0.3482(3) 0.4561(3) 0.83416(19) 0.0299(6) Uani 1 1 d . . .
H3O H 0.2858 0.4467 0.8865 0.045 Uiso 1 1 calc R . .
O4A O -0.0739(3) 0.5576(3) 0.66430(19) 0.0237(5) Uani 1 1 d . . .
H4 H -0.1869 0.5464 0.6710 0.036 Uiso 1 1 calc R . .
O4B O -0.0177(3) 0.4811(3) 0.84031(19) 0.0251(5) Uani 1 1 d . . .
C22 C 0.1816(4) -0.0078(4) 0.2745(3) 0.0242(7) Uani 1 1 d . . .
H22A H 0.1314 0.0976 0.3288 0.029 Uiso 1 1 calc R . .
H22B H 0.1481 -0.1285 0.2923 0.029 Uiso 1 1 calc R . .
C23 C 0.1059(4) -0.0256(5) 0.1411(3) 0.0265(8) Uani 1 1 d . . .
H23A H 0.0947 0.1018 0.1289 0.032 Uiso 1 1 calc R . .
H23B H -0.0192 -0.1047 0.1095 0.032 Uiso 1 1 calc R . .
C24 C 0.2542(4) -0.1234(5) 0.0782(3) 0.0300(8) Uani 1 1 d . . .
H24A H 0.2370 -0.2629 0.0661 0.036 Uiso 1 1 calc R . .
H24B H 0.2483 -0.1012 -0.0027 0.036 Uiso 1 1 calc R . .
C25 C 0.4393(4) -0.0293(5) 0.1668(3) 0.0313(8) Uani 1 1 d . . .
H25A H 0.5330 -0.1215 0.1652 0.038 Uiso 1 1 calc R . .
H25B H 0.4917 0.0816 0.1452 0.038 Uiso 1 1 calc R . .
N21 N 0.3921(3) 0.0347(3) 0.2918(2) 0.0227(6) Uani 1 1 d . . .
H21A H 0.4534 -0.0298 0.3421 0.027 Uiso 1 1 calc R . .
H21B H 0.4301 0.1638 0.3278 0.027 Uiso 1 1 calc R . .
O1W O 0.2248(3) 0.8675(3) 0.5622(2) 0.0252(5) Uani 1 1 d D . .
H1W H 0.110(3) 0.823(6) 0.528(3) 0.079(15) Uiso 1 1 d D . .
H2W H 0.291(4) 0.817(6) 0.514(3) 0.078(16) Uiso 1 1 d D . .
O2W O 0.2997(3) 0.3572(3) 1.0369(2) 0.0294(6) Uani 1 1 d D . .
H21W H 0.406(3) 0.411(9) 1.081(5) 0.19(3) Uiso 1 1 d D . .
H22W H 0.217(4) 0.402(5) 1.074(3) 0.053(13) Uiso 1 1 d D . .
 
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
C1 0.0194(14) 0.0223(18) 0.0133(15) 0.0067(13) 0.0048(12) 0.0026(13)
C2 0.0172(14) 0.0154(16) 0.0213(16) 0.0048(13) 0.0049(12) 0.0007(12)
C3 0.0168(14) 0.0238(17) 0.0207(16) 0.0079(14) 0.0039(13) 0.0017(12)
C4 0.0210(15) 0.0157(16) 0.0177(16) -0.0010(13) 0.0054(13) 0.0014(12)
O1A 0.0206(10) 0.0190(12) 0.0252(12) 0.0072(9) 0.0068(9) 0.0053(8)
O1B 0.0160(10) 0.0194(12) 0.0248(12) 0.0062(9) 0.0048(9) 0.0017(8)
O2 0.0174(10) 0.0202(12) 0.0314(13) 0.0033(10) 0.0041(9) 0.0035(9)
O3 0.0180(11) 0.0553(16) 0.0213(12) 0.0168(11) 0.0072(9) 0.0080(10)
O4A 0.0178(10) 0.0293(13) 0.0267(12) 0.0108(10) 0.0073(9) 0.0048(9)
O4B 0.0191(11) 0.0347(14) 0.0243(12) 0.0101(10) 0.0095(9) 0.0033(9)
C22 0.0196(15) 0.0243(18) 0.0290(18) 0.0081(14) 0.0061(13) 0.0016(13)
C23 0.0245(16) 0.0279(19) 0.0244(18) 0.0094(15) -0.0017(14) -0.0014(13)
C24 0.0353(18) 0.0261(19) 0.0243(18) 0.0031(15) 0.0032(15) 0.0028(14)
C25 0.0305(17) 0.032(2) 0.0295(19) 0.0048(15) 0.0088(15) 0.0050(15)
N21 0.0237(13) 0.0195(14) 0.0216(14) 0.0041(11) -0.0002(11) 0.0032(10)
O1W 0.0188(11) 0.0251(13) 0.0287(13) 0.0044(10) 0.0042(11) 0.0014(9)
O2W 0.0256(12) 0.0310(14) 0.0332(14) 0.0081(11) 0.0122(11) 0.0055(10)
 
_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 O1A 1.248(3) . ?
C1 O1B 1.270(3) . ?
C1 C2 1.521(4) . ?
C2 O2 1.414(3) . ?
C2 C3 1.518(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.412(3) . ?
C3 C4 1.513(4) . ?
C3 H3 1.0000 . ?
C4 O4B 1.209(3) . ?
C4 O4A 1.310(3) . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C22 N21 1.504(4) . ?
C22 C23 1.505(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.513(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.507(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21A 0.9200 . ?
N21 H21B 0.9200 . ?
O1W H1W 0.848(18) . ?
O1W H2W 0.833(18) . ?
O2W H21W 0.84(2) . ?
O2W H22W 0.839(18) . ?
 
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
O1A C1 O1B 124.9(3) . . ?
O1A C1 C2 118.7(3) . . ?
O1B C1 C2 116.3(2) . . ?
O2 C2 C3 110.5(2) . . ?
O2 C2 C1 112.8(2) . . ?
C3 C2 C1 109.2(2) . . ?
O2 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
O3 C3 C4 110.7(2) . . ?
O3 C3 C2 110.2(2) . . ?
C4 C3 C2 111.1(2) . . ?
O3 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
O4B C4 O4A 125.3(3) . . ?
O4B C4 C3 122.7(3) . . ?
O4A C4 C3 112.0(3) . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
N21 C22 C23 104.0(2) . . ?
N21 C22 H22A 111.0 . . ?
C23 C22 H22A 111.0 . . ?
N21 C22 H22B 111.0 . . ?
C23 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C22 C23 C24 103.1(2) . . ?
C22 C23 H23A 111.1 . . ?
C24 C23 H23A 111.1 . . ?
C22 C23 H23B 111.1 . . ?
C24 C23 H23B 111.1 . . ?
H23A C23 H23B 109.1 . . ?
C25 C24 C23 103.6(3) . . ?
C25 C24 H24A 111.0 . . ?
C23 C24 H24A 111.0 . . ?
C25 C24 H24B 111.0 . . ?
C23 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
N21 C25 C24 105.4(2) . . ?
N21 C25 H25A 110.7 . . ?
C24 C25 H25A 110.7 . . ?
N21 C25 H25B 110.7 . . ?
C24 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
C22 N21 C25 107.9(2) . . ?
C22 N21 H21A 110.1 . . ?
C25 N21 H21A 110.1 . . ?
C22 N21 H21B 110.1 . . ?
C25 N21 H21B 110.1 . . ?
H21A N21 H21B 108.4 . . ?
H1W O1W H2W 107(3) . . ?
H21W O2W H22W 108(3) . . ?
 
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
O2 H2O O1A  0.84 2.22 2.676(3) 114.2 .
O3 H3O O2W  0.84 2.02 2.726(3) 141.6 .
O3 H3O O4B  0.84 2.22 2.691(3) 115.9 .
O2 H2O O1W  0.84 2.05 2.783(3) 145.6 1_545
O4A H4 O1B  0.84 1.71 2.525(3) 162.9 1_455
N21 H21A O1A  0.92 1.97 2.835(3) 155.4 2_656
N21 H21B O1B  0.92 1.98 2.844(3) 155.8 2_666
O1W H2W O1A  0.833(18) 1.962(19) 2.777(3) 166(4) 2_666
O1W H1W O2  0.848(18) 1.96(2) 2.793(3) 165(4) 2_566
O2W H21W O3  0.84(2) 1.91(2) 2.752(4) 173(7) 2_667
O2W H22W O4B  0.839(18) 2.014(19) 2.852(3) 177(4) 2_567
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.305
_refine_diff_density_min   -0.286
_refine_diff_density_rms    0.074
