 
data_04mbh0607
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
1-Butylammonium DL-tartrate hydrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H19 N O7'
_chemical_formula_weight          241.24
 
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'
 '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            Monoclinic
_symmetry_space_group_name_H-M    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    7.388(3)
_cell_length_b                    14.227(5)
_cell_length_c                    21.744(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.87(3)
_cell_angle_gamma                 90.00
_cell_volume                      2280.3(14)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5055
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.405
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1040
_exptl_absorpt_coefficient_mu     0.123
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9854
_exptl_absorpt_correction_T_max   0.9963
_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             23440
_diffrn_reflns_av_R_equivalents   0.0618
_diffrn_reflns_av_sigmaI/netI     0.0688
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          3.11
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5223
_reflns_number_gt                 3511
_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)+(0.0402P)²+0.7799P] 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          5223
_refine_ls_number_parameters      321
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0954
_refine_ls_R_factor_gt            0.0516
_refine_ls_wR_factor_ref          0.1099
_refine_ls_wR_factor_gt           0.0952
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_restrained_S_all       1.036
_refine_ls_shift/su_max           0.000
_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 0.1061(2) 0.58021(12) 0.11521(8) 0.0147(4) Uani 1 1 d . . .
C2 C 0.3133(2) 0.59032(13) 0.11525(8) 0.0156(4) Uani 1 1 d . . .
H2 H 0.3453 0.6573 0.1072 0.019 Uiso 1 1 calc R . .
C3 C 0.4019(2) 0.55956(13) 0.17748(8) 0.0152(4) Uani 1 1 d . . .
H3 H 0.3661 0.6037 0.2103 0.018 Uiso 1 1 calc R . .
C4 C 0.6076(2) 0.55711(13) 0.17671(8) 0.0159(4) Uani 1 1 d . . .
O1A O 0.02591(16) 0.63428(9) 0.15142(6) 0.0177(3) Uani 1 1 d . . .
O1B O 0.03095(16) 0.52158(9) 0.08031(6) 0.0202(3) Uani 1 1 d . . .
O2 O 0.38572(16) 0.53164(9) 0.07052(6) 0.0188(3) Uani 1 1 d . . .
H2O H 0.3408 0.5465 0.0353 0.028 Uiso 1 1 calc R . .
O3 O 0.34708(16) 0.46763(9) 0.19148(6) 0.0190(3) Uani 1 1 d . . .
H3O H 0.2478 0.4697 0.2081 0.028 Uiso 1 1 calc R . .
O4A O 0.69665(16) 0.49215(9) 0.19799(6) 0.0234(3) Uani 1 1 d . . .
O4B O 0.67615(16) 0.63193(9) 0.15184(6) 0.0202(3) Uani 1 1 d . . .
H4 H 0.7897 0.6271 0.1531 0.030 Uiso 1 1 calc R . .
C21 C 0.6509(3) 0.35459(17) 0.46504(10) 0.0325(5) Uani 1 1 d . . .
H21A H 0.6262 0.3829 0.5047 0.049 Uiso 1 1 calc R . .
H21B H 0.7665 0.3207 0.4692 0.049 Uiso 1 1 calc R . .
H21C H 0.5533 0.3107 0.4523 0.049 Uiso 1 1 calc R . .
C22 C 0.6614(3) 0.43133(15) 0.41676(10) 0.0294(5) Uani 1 1 d . . .
H22A H 0.7637 0.4736 0.4293 0.035 Uiso 1 1 calc R . .
H22B H 0.5486 0.4690 0.4160 0.035 Uiso 1 1 calc R . .
C23 C 0.6867(3) 0.39580(15) 0.35182(9) 0.0235(4) Uani 1 1 d . . .
H23B H 0.7280 0.4484 0.3265 0.028 Uiso 1 1 calc R . .
H23A H 0.7824 0.3470 0.3537 0.028 Uiso 1 1 calc R . .
C24 C 0.5145(2) 0.35515(14) 0.32134(9) 0.0203(4) Uani 1 1 d . . .
H24B H 0.4785 0.2991 0.3446 0.024 Uiso 1 1 calc R . .
H24A H 0.4159 0.4021 0.3223 0.024 Uiso 1 1 calc R . .
N25 N 0.53928(19) 0.32829(11) 0.25646(7) 0.0171(3) Uani 1 1 d . . .
H25A H 0.6419 0.2932 0.2549 0.020(5) Uiso 1 1 calc R . .
H25B H 0.5491 0.3811 0.2333 0.039(7) Uiso 1 1 calc R . .
H25C H 0.4420 0.2941 0.2415 0.031(6) Uiso 1 1 calc R . .
C31 C 0.8734(2) 0.67977(13) 0.30318(8) 0.0154(4) Uani 1 1 d . . .
C32 C 1.0767(2) 0.66456(13) 0.29989(8) 0.0154(4) Uani 1 1 d . . .
H32 H 1.0997 0.5974 0.2894 0.018 Uiso 1 1 calc R . .
C33 C 1.1768(2) 0.68778(13) 0.36151(9) 0.0170(4) Uani 1 1 d . . .
H33 H 1.1478 0.6382 0.3919 0.020 Uiso 1 1 calc R . .
C34 C 1.3824(2) 0.69056(13) 0.35736(9) 0.0169(4) Uani 1 1 d . . .
O31A O 0.79801(16) 0.62025(9) 0.33865(6) 0.0212(3) Uani 1 1 d . . .
H31 H 0.6853 0.6290 0.3365 0.032 Uiso 1 1 calc R . .
O31B O 0.79520(17) 0.74268(10) 0.27439(7) 0.0251(3) Uani 1 1 d . . .
O32 O 1.14328(16) 0.72338(9) 0.25373(6) 0.0177(3) Uani 1 1 d . . .
H32O H 1.1116 0.7015 0.2188 0.027 Uiso 1 1 calc R . .
O33 O 1.11481(16) 0.77528(9) 0.38289(6) 0.0219(3) Uani 1 1 d . . .
H33O H 1.2041 0.8082 0.3956 0.033 Uiso 1 1 calc R . .
O34A O 1.45964(16) 0.76372(9) 0.37579(6) 0.0224(3) Uani 1 1 d . . .
O34B O 1.45766(16) 0.61894(9) 0.33577(7) 0.0225(3) Uani 1 1 d . . .
C41 C 0.8484(3) 0.57158(15) 0.56924(11) 0.0336(5) Uani 1 1 d . . .
H41A H 0.8725 0.5564 0.6130 0.050 Uiso 1 1 calc R . .
H41B H 0.9441 0.5446 0.5456 0.050 Uiso 1 1 calc R . .
H41C H 0.7309 0.5453 0.5544 0.050 Uiso 1 1 calc R . .
C42 C 0.8451(3) 0.67739(14) 0.56101(9) 0.0234(4) Uani 1 1 d . . .
H42A H 0.9610 0.7039 0.5788 0.028 Uiso 1 1 calc R . .
H42B H 0.7461 0.7039 0.5841 0.028 Uiso 1 1 calc R . .
C43 C 0.8177(3) 0.70713(13) 0.49402(9) 0.0214(4) Uani 1 1 d . . .
H43A H 0.9229 0.6863 0.4717 0.026 Uiso 1 1 calc R . .
H43B H 0.7081 0.6758 0.4750 0.026 Uiso 1 1 calc R . .
C44 C 0.7966(3) 0.81232(14) 0.48728(9) 0.0225(4) Uani 1 1 d . . .
H44A H 0.6867 0.8329 0.5072 0.027 Uiso 1 1 calc R . .
H44B H 0.9027 0.8440 0.5084 0.027 Uiso 1 1 calc R . .
N45 N 0.7814(2) 0.84029(11) 0.42137(7) 0.0189(4) Uani 1 1 d . . .
H45A H 0.6823 0.8123 0.4021 0.036(6) Uiso 1 1 calc R . .
H45B H 0.8827 0.8218 0.4031 0.042(7) Uiso 1 1 calc R . .
H45C H 0.7698 0.9038 0.4185 0.038(7) Uiso 1 1 calc R . .
O1W O 0.28588(18) 0.56683(9) -0.04767(6) 0.0206(3) Uani 1 1 d D . .
H1W H 0.190(2) 0.5366(17) -0.0598(12) 0.051(8) Uiso 1 1 d D . .
H2W H 0.373(2) 0.5392(17) -0.0626(12) 0.059(9) Uiso 1 1 d D . .
O2W O 0.04304(18) 0.42968(10) 0.24454(7) 0.0233(3) Uani 1 1 d D . .
H21W H -0.057(3) 0.4473(16) 0.2284(12) 0.059(9) Uiso 1 1 d D . .
H22W H 0.044(3) 0.3709(11) 0.2417(12) 0.049(8) 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 1.234(2) . ?
C1 O1A 1.275(2) . ?
C1 C2 1.537(2) . ?
C2 O2 1.414(2) . ?
C2 C3 1.527(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.409(2) . ?
C3 C4 1.521(2) . ?
C3 H3 1.0000 . ?
C4 O4A 1.208(2) . ?
C4 O4B 1.311(2) . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4B H4 0.8400 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.523(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.509(3) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C24 N25 1.485(2) . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
C31 O31B 1.216(2) . ?
C31 O31A 1.296(2) . ?
C31 C32 1.524(2) . ?
C32 O32 1.420(2) . ?
C32 C33 1.522(3) . ?
C32 H32 1.0000 . ?
C33 O33 1.415(2) . ?
C33 C34 1.529(2) . ?
C33 H33 1.0000 . ?
C34 O34A 1.240(2) . ?
C34 O34B 1.266(2) . ?
O31A H31 0.8400 . ?
O32 H32O 0.8400 . ?
O33 H33O 0.8400 . ?
C41 C42 1.516(3) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.517(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.511(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 N45 1.484(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
N45 H45A 0.9100 . ?
N45 H45B 0.9100 . ?
N45 H45C 0.9100 . ?
O1W H1W 0.857(16) . ?
O1W H2W 0.840(16) . ?
O2W H21W 0.833(16) . ?
O2W H22W 0.839(16) . ?
 
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 125.39(16) . . ?
O1B C1 C2 118.04(16) . . ?
O1A C1 C2 116.56(16) . . ?
O2 C2 C3 106.29(14) . . ?
O2 C2 C1 111.56(15) . . ?
C3 C2 C1 109.96(15) . . ?
O2 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
O3 C3 C4 106.47(14) . . ?
O3 C3 C2 110.18(15) . . ?
C4 C3 C2 111.47(15) . . ?
O3 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
O4A C4 O4B 124.30(17) . . ?
O4A C4 C3 122.13(17) . . ?
O4B C4 C3 113.57(15) . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4B 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 . . ?
C21 C22 C23 114.65(18) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 112.46(16) . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
H23B C23 H23A 107.8 . . ?
N25 C24 C23 111.21(15) . . ?
N25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
N25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
H24B C24 H24A 108.0 . . ?
C24 N25 H25A 109.5 . . ?
C24 N25 H25B 109.5 . . ?
H25A N25 H25B 109.5 . . ?
C24 N25 H25C 109.5 . . ?
H25A N25 H25C 109.5 . . ?
H25B N25 H25C 109.5 . . ?
O31B C31 O31A 125.37(17) . . ?
O31B C31 C32 121.07(16) . . ?
O31A C31 C32 113.56(16) . . ?
O32 C32 C33 108.89(14) . . ?
O32 C32 C31 109.80(15) . . ?
C33 C32 C31 110.45(15) . . ?
O32 C32 H32 109.2 . . ?
C33 C32 H32 109.2 . . ?
C31 C32 H32 109.2 . . ?
O33 C33 C32 109.35(15) . . ?
O33 C33 C34 109.96(15) . . ?
C32 C33 C34 112.28(15) . . ?
O33 C33 H33 108.4 . . ?
C32 C33 H33 108.4 . . ?
C34 C33 H33 108.4 . . ?
O34A C34 O34B 126.24(17) . . ?
O34A C34 C33 116.11(16) . . ?
O34B C34 C33 117.65(16) . . ?
C31 O31A H31 109.5 . . ?
C32 O32 H32O 109.5 . . ?
C33 O33 H33O 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C41 C42 C43 112.97(17) . . ?
C41 C42 H42A 109.0 . . ?
C43 C42 H42A 109.0 . . ?
C41 C42 H42B 109.0 . . ?
C43 C42 H42B 109.0 . . ?
H42A C42 H42B 107.8 . . ?
C44 C43 C42 112.06(16) . . ?
C44 C43 H43A 109.2 . . ?
C42 C43 H43A 109.2 . . ?
C44 C43 H43B 109.2 . . ?
C42 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
N45 C44 C43 111.09(16) . . ?
N45 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
N45 C44 H44B 109.4 . . ?
C43 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
C44 N45 H45A 109.5 . . ?
C44 N45 H45B 109.5 . . ?
H45A N45 H45B 109.5 . . ?
C44 N45 H45C 109.5 . . ?
H45A N45 H45C 109.5 . . ?
H45B N45 H45C 109.5 . . ?
H1W O1W H2W 107(2) . . ?
H21W O2W H22W 106(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 O1W  0.84 1.85 2.673(2) 167.7 .
O3 H3O O2W  0.84 1.84 2.649(2) 160.0 .
N25 H25B O4A  0.91 2.09 2.933(2) 152.7 .
N25 H25B O3  0.91 2.09 2.770(2) 130.1 .
O33 H33O O34A  0.84 2.06 2.5680(19) 118.0 .
N45 H45B O33  0.91 1.92 2.811(2) 167.2 .
O4B H4 O1A  0.84 1.75 2.5850(19) 171.5 1_655
O32 H32O O1A  0.84 1.83 2.6546(19) 168.5 1_655
N25 H25A O32  0.91 1.89 2.801(2) 176.2 2_745
N25 H25C O31B  0.91 1.91 2.796(2) 164.3 2_645
O2W H22W O31B  0.839(16) 2.219(18) 2.957(2) 147(2) 2_645
O2W H22W O32  0.839(16) 2.52(2) 3.243(2) 145(2) 2_645
O31A H31 O34B  0.84 1.69 2.5112(19) 166.3 1_455
N45 H45A O34A  0.91 1.84 2.739(2) 169.2 1_455
O2W H21W O4A  0.833(16) 2.001(16) 2.831(2) 174(3) 1_455
O33 H33O O1W  0.84 2.23 2.944(2) 143.6 4_676
O1W H1W O1B  0.857(16) 1.856(16) 2.7095(19) 174(2) 3_565
O1W H2W O2  0.840(16) 2.063(17) 2.8738(19) 162(3) 3_665
N45 H45C O2  0.91 2.17 2.999(2) 150.7 2_655
N45 H45C O1B  0.91 2.23 2.930(2) 133.4 2_655
N45 H45C O3  0.91 2.65 3.145(2) 115.2 2_655
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.286
_refine_diff_density_min   -0.320
_refine_diff_density_rms    0.058
