 
data_07skc0001pbca
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Di(1-butylammonium) DL-tartrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H28 N2 O6'
_chemical_formula_weight          296.36
 
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            orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    13.3732(16)
_cell_length_b                    8.5025(9)
_cell_length_c                    27.693(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3148.9(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2256
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.11
_exptl_crystal_size_mid           0.09
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.250
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1296
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9892
_exptl_absorpt_correction_T_max   0.9980
_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             13540
_diffrn_reflns_av_R_equivalents   0.0955
_diffrn_reflns_av_sigmaI/netI     0.1238
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        35
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3058
_reflns_number_gt                 1695
_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)+(0.0000P)²+19.3032P] 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_number_reflns          3058
_refine_ls_number_parameters      187
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2187
_refine_ls_R_factor_gt            0.1244
_refine_ls_wR_factor_ref          0.2353
_refine_ls_wR_factor_gt           0.1932
_refine_ls_goodness_of_fit_ref    1.145
_refine_ls_restrained_S_all       1.145
_refine_ls_shift/su_max           0.011
_refine_ls_shift/su_mean          0.001
 
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 0.5053(5) 0.2372(7) 0.4324(2) 0.0256(14) Uani 1 1 d . . .
C2 C 0.5602(4) 0.0971(7) 0.4088(2) 0.0288(15) Uani 1 1 d . . .
H2 H 0.5151 0.0550 0.3830 0.035 Uiso 1 1 calc R . .
C3 C 0.5780(4) -0.0361(7) 0.4445(2) 0.0268(14) Uani 1 1 d . . .
H3 H 0.5115 -0.0788 0.4544 0.032 Uiso 1 1 calc R . .
C4 C 0.6371(5) -0.1689(7) 0.4211(2) 0.0284(14) Uani 1 1 d . . .
O1A O 0.5434(3) 0.3710(5) 0.42796(14) 0.0301(10) Uani 1 1 d . . .
O1B O 0.4242(3) 0.2085(5) 0.45386(15) 0.0322(11) Uani 1 1 d . . .
O2 O 0.6503(3) 0.1437(5) 0.38586(14) 0.0289(10) Uani 1 1 d . . .
H20 H 0.6915 0.1737 0.4068 0.043 Uiso 1 1 calc R . .
O3 O 0.6259(3) 0.0257(5) 0.48657(13) 0.0284(10) Uani 1 1 d . . .
H3O H 0.6232 -0.0410 0.5089 0.043 Uiso 1 1 calc R . .
O4A O 0.5999(3) -0.2248(5) 0.38302(15) 0.0358(11) Uani 1 1 d . . .
O4B O 0.7171(3) -0.2124(5) 0.44096(15) 0.0332(11) Uani 1 1 d . . .
C21 C 0.4087(5) 0.4313(10) 0.2295(2) 0.054(2) Uani 1 1 d . . .
H21A H 0.3734 0.3500 0.2479 0.080 Uiso 1 1 calc R . .
H21B H 0.3996 0.4123 0.1949 0.080 Uiso 1 1 calc R . .
H21C H 0.3816 0.5349 0.2379 0.080 Uiso 1 1 calc R . .
C22 C 0.5184(5) 0.4261(9) 0.2416(2) 0.0419(18) Uani 1 1 d . . .
H22A H 0.5536 0.5066 0.2221 0.050 Uiso 1 1 calc R . .
H22B H 0.5453 0.3219 0.2323 0.050 Uiso 1 1 calc R . .
C23 C 0.5403(5) 0.4548(8) 0.2947(2) 0.0350(16) Uani 1 1 d . . .
H23A H 0.5114 0.5573 0.3042 0.042 Uiso 1 1 calc R . .
H23B H 0.5073 0.3721 0.3141 0.042 Uiso 1 1 calc R . .
C24 C 0.6511(5) 0.4550(8) 0.3059(2) 0.0315(15) Uani 1 1 d . . .
H24A H 0.6795 0.3502 0.2985 0.038 Uiso 1 1 calc R . .
H24B H 0.6852 0.5334 0.2853 0.038 Uiso 1 1 calc R . .
N25 N 0.6694(4) 0.4925(6) 0.35667(17) 0.0283(12) Uani 1 1 d . . .
H25A H 0.6408 0.4177 0.3757 0.042 Uiso 1 1 calc R . .
H25B H 0.6425 0.5880 0.3637 0.042 Uiso 1 1 calc R . .
H25C H 0.7365 0.4950 0.3622 0.042 Uiso 1 1 calc R . .
C31 C 0.7612(6) -0.1783(10) 0.6691(2) 0.056(2) Uani 1 1 d . . .
H31A H 0.7691 -0.0712 0.6816 0.084 Uiso 1 1 calc R . .
H31B H 0.7803 -0.2542 0.6940 0.084 Uiso 1 1 calc R . .
H31C H 0.6913 -0.1955 0.6599 0.084 Uiso 1 1 calc R . .
C32 C 0.8279(5) -0.1998(8) 0.6251(2) 0.0419(18) Uani 1 1 d . . .
H32A H 0.8168 -0.3061 0.6115 0.050 Uiso 1 1 calc R . .
H32B H 0.8987 -0.1926 0.6352 0.050 Uiso 1 1 calc R . .
C33 C 0.8076(5) -0.0771(8) 0.5861(2) 0.0333(16) Uani 1 1 d . . .
H33A H 0.7349 -0.0725 0.5796 0.040 Uiso 1 1 calc R . .
H33B H 0.8291 0.0275 0.5979 0.040 Uiso 1 1 calc R . .
C34 C 0.8620(5) -0.1141(7) 0.5397(2) 0.0316(15) Uani 1 1 d . . .
H34A H 0.9344 -0.1241 0.5463 0.038 Uiso 1 1 calc R . .
H34B H 0.8379 -0.2159 0.5268 0.038 Uiso 1 1 calc R . .
N35 N 0.8453(4) 0.0124(6) 0.50280(18) 0.0322(13) Uani 1 1 d . . .
H35A H 0.8811 -0.0100 0.4757 0.048 Uiso 1 1 calc R . .
H35B H 0.8656 0.1065 0.5150 0.048 Uiso 1 1 calc R . .
H35C H 0.7791 0.0174 0.4953 0.048 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 1.254(7) . ?
C1 O1B 1.259(7) . ?
C1 C2 1.546(8) . ?
C2 O2 1.419(7) . ?
C2 C3 1.522(8) . ?
C2 H2 1.0000 . ?
C3 O3 1.430(6) . ?
C3 C4 1.523(8) . ?
C3 H3 1.0000 . ?
C4 O4B 1.258(7) . ?
C4 O4A 1.259(7) . ?
O2 H20 0.8400 . ?
O3 H3O 0.8400 . ?
C21 C22 1.506(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.519(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.514(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N25 1.462(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?
C31 C32 1.520(9) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.527(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.508(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N35 1.500(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N35 H35A 0.9100 . ?
N35 H35B 0.9100 . ?
N35 H35C 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
O1A C1 O1B 125.0(6) . . ?
O1A C1 C2 117.7(5) . . ?
O1B C1 C2 117.3(5) . . ?
O2 C2 C3 111.4(5) . . ?
O2 C2 C1 112.2(5) . . ?
C3 C2 C1 111.8(5) . . ?
O2 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
O3 C3 C4 112.7(5) . . ?
O3 C3 C2 109.1(5) . . ?
C4 C3 C2 110.9(5) . . ?
O3 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
O4B C4 O4A 126.2(6) . . ?
O4B C4 C3 118.3(5) . . ?
O4A C4 C3 115.5(5) . . ?
C2 O2 H20 109.5 . . ?
C3 O3 H3O 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 113.5(5) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 112.9(5) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
N25 C24 C23 111.3(5) . . ?
N25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
N25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 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 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C31 C32 C33 112.4(6) . . ?
C31 C32 H32A 109.1 . . ?
C33 C32 H32A 109.1 . . ?
C31 C32 H32B 109.1 . . ?
C33 C32 H32B 109.1 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 112.0(5) . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
N35 C34 C33 111.0(5) . . ?
N35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
N35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 N35 H35A 109.5 . . ?
C34 N35 H35B 109.5 . . ?
H35A N35 H35B 109.5 . . ?
C34 N35 H35C 109.5 . . ?
H35A N35 H35C 109.5 . . ?
H35B N35 H35C 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
N25 H25A O1A  0.91 1.99 2.793(6) 146.8 .
N25 H25A O2  0.91 2.35 3.084(6) 137.6 .
N35 H35C O3  0.91 2.06 2.971(6) 173.5 .
N35 H35C O4B  0.91 2.60 3.086(6) 114.0 .
O2 H20 O4B  0.84 1.82 2.640(6) 163.6 8_765
N25 H25C O2  0.91 2.08 2.848(6) 141.8 8_765
O3 H3O O1B  0.84 1.87 2.671(6) 159.2 5_656
N25 H25B O4A  0.91 1.77 2.679(6) 173.3 1_565
N35 H35B O1B  0.91 1.96 2.862(6) 171.7 4_556
N35 H35A O1A  0.91 1.95 2.820(6) 160.3 8_755
 
_diffrn_measured_fraction_theta_max    0.849
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.901
_refine_diff_density_max    0.454
_refine_diff_density_min   -0.346
_refine_diff_density_rms    0.090
