 
data_04mbh0606
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
1-Butylammonium DL-tartrate DL-tartaric acid monohydrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H25 N O13'
_chemical_formula_weight          391.33
 
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'
 'O'  'O'   0.0106   0.0060
 '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'
 
_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                    4.865(2)
_cell_length_b                    9.416(3)
_cell_length_c                    19.127(12)
_cell_angle_alpha                 98.13(3)
_cell_angle_beta                  95.13(7)
_cell_angle_gamma                 97.98(3)
_cell_volume                      853.7(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3502
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.522
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              416
_exptl_absorpt_coefficient_mu     0.140
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9726
_exptl_absorpt_correction_T_max   0.9972
_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             15063
_diffrn_reflns_av_R_equivalents   0.0922
_diffrn_reflns_av_sigmaI/netI     0.1090
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          3.63
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3899
_reflns_number_gt                 2204
_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)+(0.0546P)²+0.1828P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3899
_refine_ls_number_parameters      252
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1343
_refine_ls_R_factor_gt            0.0596
_refine_ls_wR_factor_ref          0.1354
_refine_ls_wR_factor_gt           0.1102
_refine_ls_goodness_of_fit_ref    1.021
_refine_ls_restrained_S_all       1.021
_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 1.1676(5) 0.8357(3) 0.60799(14) 0.0177(6) Uani 1 1 d . . .
C2 C 0.9378(5) 0.7751(3) 0.54801(14) 0.0177(6) Uani 1 1 d . . .
H2 H 0.8177 0.6919 0.5628 0.021 Uiso 1 1 calc R . .
C3 C 1.0655(5) 0.7178(3) 0.48170(13) 0.0174(6) Uani 1 1 d . . .
H3 H 1.1709 0.6381 0.4924 0.021 Uiso 1 1 calc R . .
C4 C 0.8385(5) 0.6583(3) 0.42133(14) 0.0176(6) Uani 1 1 d . . .
O1A O 1.2896(4) 0.7316(2) 0.62749(10) 0.0254(5) Uani 1 1 d . . .
H1 H 1.4228 0.7664 0.6590 0.038 Uiso 1 1 calc R . .
O1B O 1.2198(4) 0.9639(2) 0.63198(10) 0.0222(4) Uani 1 1 d . . .
O2 O 0.7665(3) 0.87961(19) 0.53293(10) 0.0217(4) Uani 1 1 d . . .
H2O H 0.8568 0.9634 0.5458 0.033 Uiso 1 1 calc R . .
O3 O 1.2487(3) 0.8266(2) 0.45773(9) 0.0203(4) Uani 1 1 d . . .
H3O H 1.4053 0.8388 0.4819 0.031 Uiso 1 1 calc R . .
O4A O 0.6444(4) 0.5648(2) 0.44035(9) 0.0207(4) Uani 1 1 d . . .
H4 H 0.5366 0.5232 0.4043 0.031 Uiso 1 1 calc R . .
O4B O 0.8407(4) 0.69194(19) 0.36226(9) 0.0203(4) Uani 1 1 d . . .
C21 C 0.6968(7) -0.0289(4) 0.92083(17) 0.0395(8) Uani 1 1 d . . .
H21A H 0.6270 0.0511 0.9488 0.059 Uiso 1 1 calc R . .
H21B H 0.8172 -0.0740 0.9522 0.059 Uiso 1 1 calc R . .
H21C H 0.5388 -0.1014 0.8977 0.059 Uiso 1 1 calc R . .
C22 C 0.8629(6) 0.0289(3) 0.86473(15) 0.0287(7) Uani 1 1 d . . .
H22A H 1.0090 0.1098 0.8879 0.034 Uiso 1 1 calc R . .
H22B H 0.9572 -0.0488 0.8416 0.034 Uiso 1 1 calc R . .
C23 C 0.6810(6) 0.0822(3) 0.80856(14) 0.0237(6) Uani 1 1 d . . .
H23A H 0.5306 0.0025 0.7865 0.028 Uiso 1 1 calc R . .
H23B H 0.5925 0.1628 0.8313 0.028 Uiso 1 1 calc R . .
C24 C 0.8471(5) 0.1338(3) 0.75203(14) 0.0232(6) Uani 1 1 d . . .
H24A H 1.0004 0.2119 0.7743 0.028 Uiso 1 1 calc R . .
H24B H 0.9320 0.0526 0.7286 0.028 Uiso 1 1 calc R . .
N25 N 0.6709(4) 0.1897(2) 0.69747(12) 0.0242(6) Uani 1 1 d . . .
H25B H 0.7723 0.2089 0.6612 0.036 Uiso 1 1 calc R . .
H25C H 0.6137 0.2726 0.7175 0.036 Uiso 1 1 calc R . .
H25A H 0.5191 0.1218 0.6803 0.036 Uiso 1 1 calc R . .
C31 C 1.2116(5) 0.3659(3) 0.28669(14) 0.0201(6) Uani 1 1 d . . .
C32 C 1.0087(5) 0.3808(3) 0.22380(14) 0.0188(6) Uani 1 1 d . . .
H32 H 0.8821 0.2864 0.2079 0.023 Uiso 1 1 calc R . .
C33 C 1.1713(5) 0.4202(3) 0.16261(14) 0.0186(6) Uani 1 1 d . . .
H33 H 1.2710 0.3382 0.1454 0.022 Uiso 1 1 calc R . .
C34 C 0.9693(6) 0.4463(3) 0.10245(15) 0.0223(6) Uani 1 1 d . . .
O31A O 1.3179(4) 0.2505(2) 0.28056(10) 0.0247(5) Uani 1 1 d . . .
O31B O 1.2586(4) 0.4685(2) 0.33735(10) 0.0214(4) Uani 1 1 d . . .
O32 O 0.8463(4) 0.4913(2) 0.24219(10) 0.0224(5) Uani 1 1 d . . .
H32O H 0.8916 0.5284 0.2850 0.034 Uiso 1 1 calc R . .
O33 O 1.3673(4) 0.54835(19) 0.18322(10) 0.0231(5) Uani 1 1 d . . .
H33O H 1.5218 0.5268 0.1978 0.035 Uiso 1 1 calc R . .
O34A O 0.9816(4) 0.5600(2) 0.07948(10) 0.0252(5) Uani 1 1 d . . .
O34B O 0.7820(4) 0.3309(2) 0.07975(10) 0.0294(5) Uani 1 1 d . . .
H34 H 0.6838 0.3445 0.0436 0.044 Uiso 1 1 calc R . .
O1W O 0.4969(4) 0.3284(2) 0.96134(11) 0.0260(5) Uani 1 1 d D . .
H1W H 0.355(5) 0.366(4) 0.9547(17) 0.053(12) Uiso 1 1 d D . .
H2W H 0.611(6) 0.359(4) 0.9328(18) 0.076(14) Uiso 1 1 d 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
C1 O1B 1.213(3) . ?
C1 O1A 1.295(3) . ?
C1 C2 1.516(4) . ?
C2 O2 1.418(3) . ?
C2 C3 1.525(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.417(3) . ?
C3 C4 1.512(4) . ?
C3 H3 1.0000 . ?
C4 O4B 1.217(3) . ?
C4 O4A 1.311(3) . ?
O1A H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C21 C22 1.516(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.515(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.501(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N25 1.491(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
N25 H25A 0.9100 . ?
C31 O31B 1.248(3) . ?
C31 O31A 1.262(3) . ?
C31 C32 1.522(4) . ?
C32 O32 1.416(3) . ?
C32 C33 1.530(4) . ?
C32 H32 1.0000 . ?
C33 O33 1.414(3) . ?
C33 C34 1.515(4) . ?
C33 H33 1.0000 . ?
C34 O34A 1.209(3) . ?
C34 O34B 1.311(3) . ?
O32 H32O 0.8400 . ?
O33 H33O 0.8400 . ?
O34B H34 0.8400 . ?
O1W H1W 0.822(17) . ?
O1W H2W 0.861(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
O1B C1 O1A 127.6(2) . . ?
O1B C1 C2 122.4(2) . . ?
O1A C1 C2 109.9(2) . . ?
O2 C2 C1 112.1(2) . . ?
O2 C2 C3 110.4(2) . . ?
C1 C2 C3 109.7(2) . . ?
O2 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
O3 C3 C4 107.0(2) . . ?
O3 C3 C2 112.8(2) . . ?
C4 C3 C2 110.2(2) . . ?
O3 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
O4B C4 O4A 124.8(2) . . ?
O4B C4 C3 123.5(2) . . ?
O4A C4 C3 111.7(2) . . ?
C1 O1A H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C21 112.3(3) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 111.6(2) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N25 C24 C23 111.9(2) . . ?
N25 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
N25 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 N25 H25B 109.5 . . ?
C24 N25 H25C 109.5 . . ?
H25B N25 H25C 109.5 . . ?
C24 N25 H25A 109.5 . . ?
H25B N25 H25A 109.5 . . ?
H25C N25 H25A 109.5 . . ?
O31B C31 O31A 127.4(2) . . ?
O31B C31 C32 117.4(2) . . ?
O31A C31 C32 115.2(2) . . ?
O32 C32 C31 111.1(2) . . ?
O32 C32 C33 108.3(2) . . ?
C31 C32 C33 109.6(2) . . ?
O32 C32 H32 109.3 . . ?
C31 C32 H32 109.3 . . ?
C33 C32 H32 109.3 . . ?
O33 C33 C34 107.6(2) . . ?
O33 C33 C32 112.0(2) . . ?
C34 C33 C32 109.2(2) . . ?
O33 C33 H33 109.3 . . ?
C34 C33 H33 109.3 . . ?
C32 C33 H33 109.3 . . ?
O34A C34 O34B 125.3(3) . . ?
O34A C34 C33 123.5(3) . . ?
O34B C34 C33 111.2(2) . . ?
C32 O32 H32O 109.5 . . ?
C33 O33 H33O 109.5 . . ?
C34 O34B H34 109.5 . . ?
H1W O1W H2W 107(2) . . ?
 
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 O1B  0.84 2.30 2.725(3) 111.4 .
O32 H32O O4B  0.84 2.04 2.764(3) 144.7 .
O32 H32O O31B  0.84 2.15 2.638(3) 116.7 .
O1A H1 O31A  0.84 1.67 2.448(3) 152.2 2_866
O2 H2O O3  0.84 2.12 2.758(3) 132.6 2_776
O3 H3O O2  0.84 1.89 2.732(3) 175.4 1_655
O33 H33O O32  0.84 1.82 2.654(3) 171.6 1_655
O4A H4 O31B  0.84 1.75 2.567(3) 165.4 1_455
N25 H25B O4B  0.91 2.10 2.881(3) 143.6 2_766
N25 H25B O3  0.91 2.24 3.014(3) 142.1 2_766
N25 H25C O33  0.91 2.34 3.152(3) 148.5 2_766
O1W H2W O34A  0.861(18) 2.07(2) 2.828(3) 147(3) 2_766
O1W H2W O33  0.861(18) 2.50(3) 3.233(3) 143(3) 2_766
N25 H25A O1B  0.91 1.99 2.892(3) 171.8 1_445
O34B H34 O1W  0.84 1.72 2.543(3) 165.4 1_554
O1W H1W O34A  0.822(17) 1.966(19) 2.779(3) 170(3) 2_666
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.319
_refine_diff_density_min   -0.397
_refine_diff_density_rms    0.073
