 
data_06skc0078p1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
1,1,3,3-Tetramethylbutylammonium malate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H25 N O5'
_chemical_formula_weight          263.33
 
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   0.0000
 '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            triclinic
_symmetry_space_group_name_H-M    P1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 
_cell_length_a                    6.1782(3)
_cell_length_b                    7.5786(3)
_cell_length_c                    8.0969(3)
_cell_angle_alpha                 100.526(2)
_cell_angle_beta                  91.585(2)
_cell_angle_gamma                 107.060(2)
_cell_volume                      355.00(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1592
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.232
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              144
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9906
_exptl_absorpt_correction_T_max   0.9962
_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    '10cm confocal mirrors'
_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             6071
_diffrn_reflns_av_R_equivalents   0.0394
_diffrn_reflns_av_sigmaI/netI     0.0359
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.45
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1616
_reflns_number_gt                 1540
_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)+(0.0235P)²+0.1306P] 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      none
_refine_ls_extinction_coef        ?
_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          1616
_refine_ls_number_parameters      171
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0407
_refine_ls_R_factor_gt            0.0378
_refine_ls_wR_factor_ref          0.0836
_refine_ls_wR_factor_gt           0.0813
_refine_ls_goodness_of_fit_ref    1.101
_refine_ls_restrained_S_all       1.099
_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 0.8880(4) 0.3628(3) 0.6325(3) 0.0184(5) Uani 1 1 d . . .
C2 C 0.9336(4) 0.1861(3) 0.6715(3) 0.0201(5) Uani 1 1 d . . .
H2 H 1.0357 0.2238 0.7783 0.024 Uiso 1 1 calc R . .
C3 C 1.0534(4) 0.0984(3) 0.5318(3) 0.0220(5) Uani 1 1 d . . .
H3A H 0.9537 0.0557 0.4252 0.026 Uiso 1 1 calc R . .
H3B H 1.1949 0.1931 0.5134 0.026 Uiso 1 1 calc R . .
C4 C 1.1089(4) -0.0679(3) 0.5822(3) 0.0195(5) Uani 1 1 d . . .
O1A O 1.0606(3) 0.4974(2) 0.6188(2) 0.0225(4) Uani 1 1 d . . .
O1B O 0.6859(3) 0.3617(2) 0.6200(2) 0.0212(4) Uani 1 1 d . . .
O2 O 0.7292(3) 0.0517(3) 0.6967(3) 0.0285(4) Uani 1 1 d . . .
H2A H 0.6178 0.0855 0.6690 0.043 Uiso 1 1 calc R . .
O4A O 0.9736(3) -0.2320(2) 0.5043(2) 0.0283(4) Uani 1 1 d . . .
H4A H 1.0056 -0.3179 0.5427 0.042 Uiso 1 1 calc R . .
O4B O 1.2602(3) -0.0480(2) 0.6885(2) 0.0281(4) Uani 1 1 d . . .
C21 C 0.2739(4) 0.2445(4) 1.1246(3) 0.0256(5) Uani 1 1 d . . .
H21A H 0.2787 0.1600 1.0185 0.038 Uiso 1 1 calc R . .
H21B H 0.1269 0.2693 1.1260 0.038 Uiso 1 1 calc R . .
H21C H 0.2939 0.1853 1.2195 0.038 Uiso 1 1 calc R . .
C22 C 0.4657(4) 0.4311(4) 1.1398(3) 0.0220(5) Uani 1 1 d . . .
C23 C 0.4381(4) 0.4968(3) 0.9730(3) 0.0180(4) Uani 1 1 d . . .
H23A H 0.4674 0.4020 0.8822 0.022 Uiso 1 1 calc R . .
H23B H 0.2757 0.4875 0.9548 0.022 Uiso 1 1 calc R . .
C24 C 0.5757(4) 0.6912(3) 0.9418(3) 0.0195(5) Uani 1 1 d . . .
C26 C 0.4361(5) 0.5671(4) 1.2967(3) 0.0293(6) Uani 1 1 d . . .
H26A H 0.2961 0.5996 1.2786 0.044 Uiso 1 1 calc R . .
H26B H 0.5663 0.6819 1.3170 0.044 Uiso 1 1 calc R . .
H26C H 0.4269 0.5068 1.3946 0.044 Uiso 1 1 calc R . .
C27 C 0.6922(4) 0.3896(4) 1.1630(3) 0.0275(6) Uani 1 1 d . . .
H27A H 0.6881 0.3231 1.2564 0.041 Uiso 1 1 calc R . .
H27B H 0.8166 0.5083 1.1881 0.041 Uiso 1 1 calc R . .
H27C H 0.7163 0.3109 1.0592 0.041 Uiso 1 1 calc R . .
C28 C 0.4865(4) 0.8501(3) 1.0245(3) 0.0242(5) Uani 1 1 d . . .
H28A H 0.5151 0.8712 1.1472 0.036 Uiso 1 1 calc R . .
H28B H 0.3228 0.8160 0.9941 0.036 Uiso 1 1 calc R . .
H28C H 0.5644 0.9656 0.9853 0.036 Uiso 1 1 calc R . .
C29 C 0.8324(4) 0.7448(4) 0.9793(3) 0.0239(5) Uani 1 1 d . . .
H29A H 0.9060 0.8569 0.9338 0.036 Uiso 1 1 calc R . .
H29B H 0.8864 0.6402 0.9266 0.036 Uiso 1 1 calc R . .
H29C H 0.8699 0.7718 1.1015 0.036 Uiso 1 1 calc R . .
N25 N 0.5348(3) 0.6729(3) 0.7517(3) 0.0189(4) Uani 1 1 d . . .
H25A H 0.5978 0.5868 0.6968 0.028 Uiso 1 1 calc R . .
H25B H 0.5995 0.7865 0.7235 0.028 Uiso 1 1 calc R . .
H25C H 0.3827 0.6345 0.7216 0.028 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 O1B 1.248(3) . ?
C1 O1A 1.265(3) . ?
C1 C2 1.531(3) . ?
C2 O2 1.417(3) . ?
C2 C3 1.527(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O4B 1.209(3) . ?
C4 O4A 1.311(3) . ?
O2 H2A 0.8400 . ?
O4A H4A 0.8400 . ?
C21 C22 1.538(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C26 1.535(4) . ?
C22 C27 1.535(3) . ?
C22 C23 1.544(3) . ?
C23 C24 1.540(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C28 1.522(3) . ?
C24 C29 1.524(3) . ?
C24 N25 1.527(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
 
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 126.3(2) . . ?
O1B C1 C2 117.3(2) . . ?
O1A C1 C2 116.4(2) . . ?
O2 C2 C3 110.06(19) . . ?
O2 C2 C1 111.02(18) . . ?
C3 C2 C1 111.35(19) . . ?
O2 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C4 C3 C2 109.18(19) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
O4B C4 O4A 124.0(2) . . ?
O4B C4 C3 122.3(2) . . ?
O4A C4 C3 113.8(2) . . ?
C2 O2 H2A 109.5 . . ?
C4 O4A H4A 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 . . ?
C26 C22 C27 109.7(2) . . ?
C26 C22 C21 107.8(2) . . ?
C27 C22 C21 107.6(2) . . ?
C26 C22 C23 113.8(2) . . ?
C27 C22 C23 112.6(2) . . ?
C21 C22 C23 105.02(19) . . ?
C24 C23 C22 123.1(2) . . ?
C24 C23 H23A 106.6 . . ?
C22 C23 H23A 106.6 . . ?
C24 C23 H23B 106.6 . . ?
C22 C23 H23B 106.6 . . ?
H23A C23 H23B 106.5 . . ?
C28 C24 C29 110.6(2) . . ?
C28 C24 N25 106.35(18) . . ?
C29 C24 N25 105.91(19) . . ?
C28 C24 C23 113.42(19) . . ?
C29 C24 C23 115.87(19) . . ?
N25 C24 C23 103.68(18) . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
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 . . ?
 
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 H2A O1B  0.84 2.12 2.621(2) 117.6 .
N25 H25A O1B  0.91 1.94 2.828(3) 164.4 .
O2 H2A O4B  0.84 2.17 2.767(2) 128.3 1_455
N25 H25C O1A  0.91 2.03 2.920(3) 166.4 1_455
O4A H4A O1A  0.84 1.74 2.582(2) 177.5 1_545
N25 H25B O2  0.91 1.99 2.891(3) 171.1 1_565
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.184
_refine_diff_density_min   -0.186
_refine_diff_density_rms    0.042
