 
data_06skc0059p21
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
1-Methylpiperazinium oxalate dihydrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C7 H18 N2 O6'
_chemical_formula_weight          226.23
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 '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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    8.2165(4)
_cell_length_b                    7.0534(5)
_cell_length_c                    10.0677(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  104.266(4)
_cell_angle_gamma                 90.00
_cell_volume                      565.47(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1618
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       23.26
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.11
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.329
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              244
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9773
_exptl_absorpt_correction_T_max   0.9966
_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             7091
_diffrn_reflns_av_R_equivalents   0.0657
_diffrn_reflns_av_sigmaI/netI     0.0537
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.56
_diffrn_reflns_theta_max          23.35
_reflns_number_total              738
_reflns_number_gt                 641
_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.

 Unfortunately the crystals were weakly diffracting therefore data could 
 only be collected out to 23.35deg thereby reducing the completeness and 
 unique/observed reflections ratio.
;
 
_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)+(0.0495P)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     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.058(12)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    10(10)
_refine_ls_number_reflns          738
_refine_ls_number_parameters      155
_refine_ls_number_restraints      7
_refine_ls_R_factor_all           0.0462
_refine_ls_R_factor_gt            0.0344
_refine_ls_wR_factor_ref          0.0788
_refine_ls_wR_factor_gt           0.0761
_refine_ls_goodness_of_fit_ref    1.063
_refine_ls_restrained_S_all       1.059
_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 0.1903(4) 0.2033(5) 0.8753(4) 0.0236(9) Uani 1 1 d . . .
C2 C 0.1488(4) 0.0514(5) 0.7602(4) 0.0253(9) Uani 1 1 d . . .
O1A O 0.3433(3) 0.2147(3) 0.9406(3) 0.0275(7) Uani 1 1 d . . .
O1B O 0.0738(3) 0.2984(5) 0.8971(3) 0.0365(8) Uani 1 1 d . . .
O2A O 0.2606(3) -0.0619(4) 0.7512(3) 0.0341(7) Uani 1 1 d . . .
O2B O 0.0017(3) 0.0605(4) 0.6823(3) 0.0312(7) Uani 1 1 d . . .
C22 C 0.6242(5) 0.1313(5) 0.6670(4) 0.0276(10) Uani 1 1 d . . .
H22A H 0.6478 0.0932 0.5789 0.033 Uiso 1 1 calc R . .
H22B H 0.5076 0.1795 0.6478 0.033 Uiso 1 1 calc R . .
C23 C 0.6423(5) -0.0382(5) 0.7610(4) 0.0293(9) Uani 1 1 d . . .
H23A H 0.5612 -0.1377 0.7182 0.035 Uiso 1 1 calc R . .
H23B H 0.7570 -0.0912 0.7759 0.035 Uiso 1 1 calc R . .
C25 C 0.7232(4) 0.1753(6) 0.9591(4) 0.0280(9) Uani 1 1 d . . .
H25A H 0.8411 0.1304 0.9826 0.034 Uiso 1 1 calc R . .
H25B H 0.6945 0.2142 1.0450 0.034 Uiso 1 1 calc R . .
C26 C 0.7068(5) 0.3418(5) 0.8649(4) 0.0259(9) Uani 1 1 d . . .
H26A H 0.7864 0.4423 0.9083 0.031 Uiso 1 1 calc R . .
H26B H 0.5916 0.3939 0.8476 0.031 Uiso 1 1 calc R . .
C27 C 0.7401(5) 0.4497(5) 0.6390(4) 0.0346(10) Uani 1 1 d . . .
H27A H 0.6304 0.5123 0.6222 0.052 Uiso 1 1 calc R . .
H27B H 0.7597 0.4063 0.5518 0.052 Uiso 1 1 calc R . .
H27C H 0.8283 0.5395 0.6822 0.052 Uiso 1 1 calc R . .
N21 N 0.7430(4) 0.2835(5) 0.7317(3) 0.0250(8) Uani 1 1 d . . .
H21 H 0.8507 0.2328 0.7514 0.031(11) Uiso 1 1 calc R . .
N24 N 0.6108(4) 0.0184(4) 0.8946(3) 0.0253(8) Uani 1 1 d . . .
H24A H 0.5008 0.0562 0.8813 0.030 Uiso 1 1 calc R . .
H24B H 0.6276 -0.0845 0.9526 0.030 Uiso 1 1 calc R . .
O1W O -0.1501(4) -0.1878(4) 0.4880(3) 0.0371(7) Uani 1 1 d D . .
H1W H -0.090(6) -0.256(6) 0.450(5) 0.064(17) Uiso 1 1 d D . .
H2W H -0.080(6) -0.123(9) 0.547(6) 0.11(3) Uiso 1 1 d D . .
O2W O 0.3555(3) -0.4172(4) 0.6752(3) 0.0388(8) Uani 1 1 d D . .
H21W H 0.300(5) -0.321(4) 0.685(5) 0.048(14) Uiso 1 1 d D . .
H22W H 0.282(5) -0.505(5) 0.647(5) 0.064(17) 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 0.020(2) 0.028(2) 0.024(2) 0.0022(18) 0.0068(17) -0.0003(19)
C2 0.021(2) 0.026(2) 0.029(2) 0.0041(18) 0.0078(17) 0.0011(19)
O1A 0.0181(14) 0.0323(16) 0.0306(15) -0.0069(13) 0.0032(11) 0.0003(12)
O1B 0.0185(13) 0.0444(17) 0.0450(18) -0.0165(16) 0.0051(13) 0.0018(13)
O2A 0.0237(15) 0.0343(16) 0.0414(17) -0.0084(14) 0.0026(13) 0.0067(13)
O2B 0.0203(14) 0.0355(16) 0.0354(16) -0.0059(14) 0.0024(12) -0.0002(13)
C22 0.0209(18) 0.034(2) 0.027(2) -0.0028(18) 0.0042(18) -0.0009(16)
C23 0.023(2) 0.029(2) 0.038(2) -0.0047(19) 0.0098(18) -0.0016(17)
C25 0.0228(18) 0.032(2) 0.029(2) -0.0020(19) 0.0059(16) 0.0000(18)
C26 0.020(2) 0.028(2) 0.030(2) -0.0040(17) 0.0053(18) 0.0039(16)
C27 0.034(2) 0.032(2) 0.039(2) 0.011(2) 0.0095(19) 0.0044(19)
N21 0.0208(16) 0.0234(16) 0.0307(18) 0.0047(15) 0.0060(14) 0.0050(14)
N24 0.0191(16) 0.0281(18) 0.0294(19) 0.0040(15) 0.0071(14) 0.0016(14)
O1W 0.0389(16) 0.0340(17) 0.0354(17) -0.0057(15) 0.0035(15) -0.0014(15)
O2W 0.0276(15) 0.0354(18) 0.054(2) -0.0038(16) 0.0103(14) 0.0011(15)
 
_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 1.231(5) . ?
C1 O1A 1.270(4) . ?
C1 C2 1.553(5) . ?
C2 O2A 1.238(4) . ?
C2 O2B 1.270(5) . ?
C22 N21 1.489(5) . ?
C22 C23 1.509(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N24 1.485(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 N24 1.485(5) . ?
C25 C26 1.495(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N21 1.500(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N21 1.495(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N21 H21 0.9300 . ?
N24 H24A 0.9200 . ?
N24 H24B 0.9200 . ?
O1W H1W 0.85(2) . ?
O1W H2W 0.85(2) . ?
O2W H21W 0.84(2) . ?
O2W H22W 0.86(2) . ?
 
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 125.9(3) . . ?
O1B C1 C2 118.1(3) . . ?
O1A C1 C2 115.9(3) . . ?
O2A C2 O2B 126.7(4) . . ?
O2A C2 C1 118.0(3) . . ?
O2B C2 C1 115.3(3) . . ?
N21 C22 C23 110.2(3) . . ?
N21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
N21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
N24 C23 C22 110.0(3) . . ?
N24 C23 H23A 109.7 . . ?
C22 C23 H23A 109.7 . . ?
N24 C23 H23B 109.7 . . ?
C22 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
N24 C25 C26 111.0(3) . . ?
N24 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
N24 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 N21 110.2(3) . . ?
C25 C26 H26A 109.6 . . ?
N21 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
N21 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N21 C27 H27A 109.5 . . ?
N21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 N21 C27 112.6(3) . . ?
C22 N21 C26 109.6(3) . . ?
C27 N21 C26 111.5(3) . . ?
C22 N21 H21 107.6 . . ?
C27 N21 H21 107.6 . . ?
C26 N21 H21 107.6 . . ?
C25 N24 C23 111.6(3) . . ?
C25 N24 H24A 109.3 . . ?
C23 N24 H24A 109.3 . . ?
C25 N24 H24B 109.3 . . ?
C23 N24 H24B 109.3 . . ?
H24A N24 H24B 108.0 . . ?
H1W O1W H2W 105(3) . . ?
H21W O2W H22W 105(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
N24 H24A O1A  0.92 1.91 2.733(4) 147.1 .
N24 H24A O2A  0.92 2.24 2.939(4) 132.0 .
O1W H2W O2B  0.85(2) 1.88(3) 2.692(4) 159(6) .
O2W H21W O2A  0.84(2) 2.00(2) 2.787(4) 157(4) .
N21 H21 O2B  0.93 1.98 2.786(4) 143.8 1_655
N21 H21 O1B  0.93 2.10 2.819(4) 133.3 1_655
N24 H24B O1A  0.92 1.76 2.679(4) 178.3 2_647
O1W H1W O2B  0.85(2) 2.11(2) 2.934(4) 165(5) 2_546
O2W H22W O1W  0.86(2) 1.99(3) 2.797(4) 156(5) 2_546
 
_diffrn_measured_fraction_theta_max    0.823
_diffrn_reflns_theta_full              23.35
_diffrn_measured_fraction_theta_full   0.823
_refine_diff_density_max    0.155
_refine_diff_density_min   -0.167
_refine_diff_density_rms    0.038
