#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519904.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519904
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 1,1,3,3-Tetramethylbutylammonium malate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              560
_journal_year                    2008
_chemical_formula_sum            'C12 H25 N O5'
_chemical_formula_weight         263.33
_chemical_name_systematic
;
1,1,3,3-Tetramethylbutylammonium malate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.526(2)
_cell_angle_beta                 91.585(2)
_cell_angle_gamma                107.060(2)
_cell_formula_units_Z            1
_cell_length_a                   6.1782(3)
_cell_length_b                   7.5786(3)
_cell_length_c                   8.0969(3)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     355.00(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6071
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1616
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0235P)²+0.1306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                1540
_reflns_number_total             1616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-560.cif
_cod_data_source_block           06skc0078p1
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/560)

More at:
http://ecrystals.chem.soton.ac.uk/560/
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1519904
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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 . .
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
