 
data_06skc0062p21n
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Toluidinium fumarate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H13 N O4'
_chemical_formula_weight          223.22
 
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/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    9.2008(3)
_cell_length_b                    23.6311(10)
_cell_length_c                    10.4061(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  95.173(3)
_cell_angle_gamma                 90.00
_cell_volume                      2253.33(15)
_cell_formula_units_Z             8
_cell_measurement_temperature     260(2)
_cell_measurement_reflns_used     3319
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       23.26
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.316
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              944
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9684
_exptl_absorpt_correction_T_max   0.9960
_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             22244
_diffrn_reflns_av_R_equivalents   0.0796
_diffrn_reflns_av_sigmaI/netI     0.0560
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        26
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          23.27
_reflns_number_total              3232
_reflns_number_gt                 2215
_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)+(0.0495P)²+1.0777P] 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      SHELXL
_refine_ls_extinction_coef        0.0041(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3232
_refine_ls_number_parameters      301
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0816
_refine_ls_R_factor_gt            0.0429
_refine_ls_wR_factor_ref          0.1067
_refine_ls_wR_factor_gt           0.0901
_refine_ls_goodness_of_fit_ref    0.983
_refine_ls_restrained_S_all       0.983
_refine_ls_shift/su_max           0.046
_refine_ls_shift/su_mean          0.002
 
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 0.1141(2) -0.00360(11) 0.6196(2) 0.0190(6) Uani 1 1 d . . .
C2 C 0.2300(2) -0.00020(11) 0.5290(2) 0.0195(6) Uani 1 1 d . . .
H2 H 0.2750 0.0346 0.5188 0.023 Uiso 1 1 calc R . .
C3 C 0.2725(2) -0.04347(10) 0.4629(2) 0.0205(6) Uani 1 1 d . . .
H3 H 0.2263 -0.0781 0.4710 0.025 Uiso 1 1 calc R . .
C4 C 0.3915(2) -0.03941(11) 0.3753(2) 0.0209(6) Uani 1 1 d . . .
O1A O 0.04779(16) -0.04828(7) 0.63425(15) 0.0239(4) Uani 1 1 d . . .
O1B O 0.09033(16) 0.04376(7) 0.67686(16) 0.0224(4) Uani 1 1 d . . .
H1 H 0.0275 0.0391 0.7270 0.034 Uiso 0.50 1 calc PR . .
O4A O 0.45560(17) -0.08268(7) 0.34431(16) 0.0274(4) Uani 1 1 d . . .
O4B O 0.41965(16) 0.01143(7) 0.33861(15) 0.0214(4) Uani 1 1 d . . .
H4 H 0.4875 0.0106 0.2927 0.032 Uiso 0.50 1 calc PR . .
C21 C 0.2704(3) 0.25119(12) 0.3074(3) 0.0414(8) Uani 1 1 d . . .
C22 C 0.3569(3) 0.20852(13) 0.3648(3) 0.0445(8) Uani 1 1 d . . .
H22 H 0.4365 0.2182 0.4220 0.053 Uiso 1 1 calc R . .
C23 C 0.3281(3) 0.15188(11) 0.3391(3) 0.0359(7) Uani 1 1 d . . .
H23 H 0.3874 0.1238 0.3782 0.043 Uiso 1 1 calc R . .
C24 C 0.2102(2) 0.13813(10) 0.2547(2) 0.0225(6) Uani 1 1 d . . .
C25 C 0.1212(3) 0.17932(11) 0.1983(3) 0.0353(7) Uani 1 1 d . . .
H25 H 0.0409 0.1695 0.1420 0.042 Uiso 1 1 calc R . .
C26 C 0.1515(3) 0.23548(12) 0.2257(3) 0.0428(8) Uani 1 1 d . . .
H26 H 0.0901 0.2633 0.1881 0.051 Uiso 1 1 calc R . .
C27 C 0.3052(4) 0.31278(13) 0.3356(4) 0.0681(11) Uani 1 1 d . . .
H27A H 0.2851 0.3215 0.4224 0.102 Uiso 1 1 calc R . .
H27B H 0.2462 0.3362 0.2764 0.102 Uiso 1 1 calc R . .
H27C H 0.4065 0.3197 0.3260 0.102 Uiso 1 1 calc R . .
N24 N 0.1781(2) 0.07839(8) 0.2255(2) 0.0225(5) Uani 1 1 d . . .
H24A H 0.2580 0.0578 0.2447 0.038(8) Uiso 1 1 calc R . .
H24B H 0.1492 0.0747 0.1419 0.050(9) Uiso 1 1 calc R . .
H24C H 0.1075 0.0665 0.2721 0.046(9) Uiso 1 1 calc R . .
C31 C 0.5717(2) 0.04888(10) 0.0912(2) 0.0186(6) Uani 1 1 d . . .
C32 C 0.6816(2) 0.05394(9) -0.0044(2) 0.0193(6) Uani 1 1 d . . .
H32 H 0.6488 0.0586 -0.0909 0.023 Uiso 1 1 calc R . .
C33 C 0.8236(2) 0.05218(9) 0.0279(2) 0.0185(6) Uani 1 1 d . . .
H33 H 0.8559 0.0477 0.1146 0.022 Uiso 1 1 calc R . .
C34 C 0.9345(3) 0.05693(10) -0.0665(2) 0.0186(6) Uani 1 1 d . . .
O31A O 0.61656(16) 0.02330(7) 0.19708(15) 0.0222(4) Uani 1 1 d . . .
H31 H 0.5481 0.0192 0.2416 0.033 Uiso 0.50 1 calc PR . .
O31B O 0.44639(16) 0.06768(7) 0.06686(15) 0.0235(4) Uani 1 1 d . . .
O34A O 0.88861(15) 0.04386(7) -0.18361(15) 0.0222(4) Uani 1 1 d . . .
H34 H 0.9571 0.0448 -0.2289 0.033 Uiso 0.50 1 calc PR . .
O34B O 1.06137(16) 0.07141(7) -0.03162(15) 0.0237(4) Uani 1 1 d . . .
C41 C 0.7552(3) -0.27514(11) 0.2111(3) 0.0356(7) Uani 1 1 d . . .
C42 C 0.7920(3) -0.23911(12) 0.3130(3) 0.0437(8) Uani 1 1 d . . .
H42 H 0.8351 -0.2538 0.3902 0.052 Uiso 1 1 calc R . .
C43 C 0.7658(3) -0.18140(12) 0.3026(3) 0.0386(8) Uani 1 1 d . . .
H43 H 0.7915 -0.1576 0.3721 0.046 Uiso 1 1 calc R . .
C44 C 0.7019(2) -0.15983(10) 0.1890(2) 0.0220(6) Uani 1 1 d . . .
C45 C 0.6646(3) -0.19458(12) 0.0861(3) 0.0366(7) Uani 1 1 d . . .
H45 H 0.6215 -0.1798 0.0090 0.044 Uiso 1 1 calc R . .
C46 C 0.6917(3) -0.25208(12) 0.0984(3) 0.0434(8) Uani 1 1 d . . .
H46 H 0.6663 -0.2757 0.0286 0.052 Uiso 1 1 calc R . .
C47 C 0.7825(3) -0.33789(12) 0.2231(3) 0.0550(9) Uani 1 1 d . . .
H47A H 0.6918 -0.3578 0.2069 0.083 Uiso 1 1 calc R . .
H47B H 0.8248 -0.3464 0.3086 0.083 Uiso 1 1 calc R . .
H47C H 0.8482 -0.3494 0.1614 0.083 Uiso 1 1 calc R . .
N44 N 0.67102(19) -0.09910(8) 0.18009(19) 0.0231(5) Uani 1 1 d . . .
H44A H 0.7520 -0.0797 0.2038 0.035 Uiso 1 1 calc R . .
H44B H 0.6025 -0.0904 0.2319 0.035 Uiso 1 1 calc R . .
H44C H 0.6398 -0.0903 0.0991 0.035 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 O1A 1.236(3) . ?
C1 O1B 1.295(3) . ?
C1 C2 1.488(3) . ?
C2 C3 1.311(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.490(3) . ?
C3 H3 0.9300 . ?
C4 O4A 1.237(3) . ?
C4 O4B 1.294(3) . ?
O1B H1 0.8200 . ?
O4B H4 0.8200 . ?
C21 C26 1.375(4) . ?
C21 C22 1.386(4) . ?
C21 C27 1.513(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 N24 1.469(3) . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N24 H24A 0.8900 . ?
N24 H24B 0.8900 . ?
N24 H24C 0.8900 . ?
C31 O31B 1.240(3) . ?
C31 O31A 1.291(3) . ?
C31 C32 1.486(3) . ?
C32 C33 1.321(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.483(3) . ?
C33 H33 0.9300 . ?
C34 O34B 1.239(3) . ?
C34 O34A 1.291(3) . ?
O31A H31 0.8200 . ?
O34A H34 0.8200 . ?
C41 C46 1.374(4) . ?
C41 C42 1.378(4) . ?
C41 C47 1.507(4) . ?
C42 C43 1.387(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.370(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.368(3) . ?
C44 N44 1.464(3) . ?
C45 C46 1.385(4) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
N44 H44A 0.8900 . ?
N44 H44B 0.8900 . ?
N44 H44C 0.8900 . ?
 
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 125.2(2) . . ?
O1A C1 C2 120.9(2) . . ?
O1B C1 C2 113.9(2) . . ?
C3 C2 C1 123.7(2) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
O4A C4 O4B 125.3(2) . . ?
O4A C4 C3 120.0(2) . . ?
O4B C4 C3 114.7(2) . . ?
C1 O1B H1 109.5 . . ?
C4 O4B H4 109.5 . . ?
C26 C21 C22 117.6(3) . . ?
C26 C21 C27 121.5(3) . . ?
C22 C21 C27 120.9(3) . . ?
C21 C22 C23 121.8(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 118.6(3) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 N24 119.5(2) . . ?
C23 C24 N24 119.5(2) . . ?
C24 C25 C26 119.5(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 121.5(3) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 N24 H24A 109.5 . . ?
C24 N24 H24B 109.5 . . ?
H24A N24 H24B 109.5 . . ?
C24 N24 H24C 109.5 . . ?
H24A N24 H24C 109.5 . . ?
H24B N24 H24C 109.5 . . ?
O31B C31 O31A 124.2(2) . . ?
O31B C31 C32 120.7(2) . . ?
O31A C31 C32 115.1(2) . . ?
C33 C32 C31 123.0(2) . . ?
C33 C32 H32 118.5 . . ?
C31 C32 H32 118.5 . . ?
C32 C33 C34 123.6(2) . . ?
C32 C33 H33 118.2 . . ?
C34 C33 H33 118.2 . . ?
O34B C34 O34A 124.2(2) . . ?
O34B C34 C33 120.9(2) . . ?
O34A C34 C33 114.9(2) . . ?
C31 O31A H31 109.5 . . ?
C34 O34A H34 109.5 . . ?
C46 C41 C42 117.9(3) . . ?
C46 C41 C47 121.0(3) . . ?
C42 C41 C47 121.1(3) . . ?
C41 C42 C43 121.2(3) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C44 C43 C42 119.4(3) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C45 C44 C43 120.6(2) . . ?
C45 C44 N44 120.3(2) . . ?
C43 C44 N44 119.0(2) . . ?
C44 C45 C46 119.1(3) . . ?
C44 C45 H45 120.5 . . ?
C46 C45 H45 120.5 . . ?
C41 C46 C45 121.8(3) . . ?
C41 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C41 C47 H47A 109.5 . . ?
C41 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C41 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 N44 H44A 109.5 . . ?
C44 N44 H44B 109.5 . . ?
H44A N44 H44B 109.5 . . ?
C44 N44 H44C 109.5 . . ?
H44A N44 H44C 109.5 . . ?
H44B N44 H44C 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
O34A H34 O1B  0.82 1.64 2.457(2) 177.1 1_654
O34A H34 O1A  0.82 2.79 3.314(2) 123.6 1_654
N24 H24A O4B  0.89 2.03 2.891(3) 163.8 .
N24 H24A O31B  0.89 2.66 3.101(3) 111.9 .
O31A H31 O4B  0.82 1.63 2.452(2) 176.2 .
O31A H31 O4A  0.82 2.80 3.350(2) 126.3 .
N44 H44B O4A  0.89 1.87 2.759(2) 172.1 .
N24 H24B O34B  0.89 1.91 2.796(3) 171.8 1_455
N24 H24C O1A  0.89 1.85 2.739(2) 174.6 3_556
N44 H44A O1B  0.89 2.01 2.856(2) 158.1 3_656
N44 H44A O34B  0.89 2.60 3.093(2) 115.9 3_755
N44 H44C O31B  0.89 1.91 2.797(3) 173.5 3_655
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              23.27
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.196
_refine_diff_density_min   -0.202
_refine_diff_density_rms    0.045
