#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519952.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_1519952
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 1-Butylammonium fumarate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              562
_journal_year                    2008
_chemical_formula_sum            'C8 H15 N O4'
_chemical_formula_weight         189.21
_chemical_name_systematic
;
1-Butylammonium fumarate
;
_space_group_IT_number           2
_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                105.47(5)
_cell_angle_beta                 99.121(5)
_cell_angle_gamma                93.957(5)
_cell_formula_units_Z            4
_cell_length_a                   9.2652(6)
_cell_length_b                   10.5292(10)
_cell_length_c                   10.5973(10)
_cell_measurement_reflns_used    4398
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     977.0(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19740
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9817
_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    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0657
_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)+(0.0862P)²+0.1591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                2463
_reflns_number_total             4473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-562.cif
_cod_data_source_block           06skc0064p-1
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/562)

More at:
http://ecrystals.chem.soton.ac.uk/562/
;
_cod_original_cell_volume        977.01(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.5918(3) -0.8949(3) 0.6338(2) 0.0270(6) Uani 1 1 d . . .
C2 C 0.7012(2) -0.9925(3) 0.6238(2) 0.0273(6) Uani 1 1 d . . .
H2 H 0.6679 -1.0824 0.6148 0.033 Uiso 1 1 calc R . .
C3 C 0.8421(3) -0.9605(3) 0.6266(2) 0.0289(6) Uani 1 1 d . . .
H3 H 0.8763 -0.8703 0.6378 0.035 Uiso 1 1 calc R . .
C4 C 0.9494(3) -1.0592(3) 0.6132(3) 0.0293(6) Uani 1 1 d . . .
O1A O 0.47353(17) -0.92163(17) 0.66740(18) 0.0316(5) Uani 1 1 d . . .
O1B O 0.62738(17) -0.78901(16) 0.60403(17) 0.0300(4) Uani 1 1 d . . .
O4A O 0.89438(17) -1.17913(17) 0.55325(19) 0.0336(5) Uani 1 1 d . . .
H4 H 0.9622 -1.2282 0.5471 0.050 Uiso 1 1 calc R . .
O4B O 1.08221(17) -1.02374(18) 0.6548(2) 0.0381(5) Uani 1 1 d . . .
C22 C 0.6545(3) -0.8570(3) 0.1798(3) 0.0375(7) Uani 1 1 d . . .
H22A H 0.5584 -0.9012 0.1252 0.045 Uiso 1 1 calc R . .
H22B H 0.7290 -0.9189 0.1596 0.045 Uiso 1 1 calc R . .
C23 C 0.6949(3) -0.7343(3) 0.1416(3) 0.0386(7) Uani 1 1 d . . .
H23A H 0.7871 -0.6861 0.2007 0.046 Uiso 1 1 calc R . .
H23B H 0.6164 -0.6755 0.1542 0.046 Uiso 1 1 calc R . .
C24 C 0.7161(3) -0.7664(3) -0.0030(3) 0.0486(8) Uani 1 1 d . . .
H24A H 0.7946 -0.8254 -0.0152 0.058 Uiso 1 1 calc R . .
H24B H 0.6240 -0.8150 -0.0617 0.058 Uiso 1 1 calc R . .
C25 C 0.7567(4) -0.6445(4) -0.0445(3) 0.0683(11) Uani 1 1 d . . .
H25A H 0.6747 -0.5904 -0.0423 0.102 Uiso 1 1 calc R . .
H25B H 0.7776 -0.6712 -0.1351 0.102 Uiso 1 1 calc R . .
H25C H 0.8442 -0.5927 0.0169 0.102 Uiso 1 1 calc R . .
N21 N 0.6449(2) -0.8296(2) 0.3232(2) 0.0322(5) Uani 1 1 d . . .
H21A H 0.7344 -0.7934 0.3740 0.048 Uiso 1 1 calc R . .
H21B H 0.6169 -0.9068 0.3407 0.048 Uiso 1 1 calc R . .
H21C H 0.5775 -0.7720 0.3426 0.048 Uiso 1 1 calc R . .
C31 C 0.9097(3) -0.6001(2) 0.5938(3) 0.0286(6) Uani 1 1 d . . .
C32 C 0.7932(2) -0.5102(2) 0.6037(3) 0.0289(6) Uani 1 1 d . . .
H32 H 0.7619 -0.4796 0.6866 0.035 Uiso 1 1 calc R . .
C33 C 0.7315(2) -0.4709(2) 0.5018(3) 0.0289(6) Uani 1 1 d . . .
H33 H 0.7620 -0.5030 0.4187 0.035 Uiso 1 1 calc R . .
C34 C 0.6170(2) -0.3794(2) 0.5105(3) 0.0274(6) Uani 1 1 d . . .
O31A O 0.91531(17) -0.67009(17) 0.47470(18) 0.0308(4) Uani 1 1 d . . .
O31B O 0.99369(19) -0.60254(18) 0.69538(19) 0.0368(5) Uani 1 1 d . . .
O34A O 0.57191(17) -0.35305(17) 0.39904(18) 0.0323(5) Uani 1 1 d . . .
H34 H 0.5026 -0.3059 0.4074 0.048 Uiso 1 1 calc R . .
O34B O 0.57199(17) -0.33439(17) 0.61462(18) 0.0318(4) Uani 1 1 d . . .
C42A C 0.2862(17) -0.7422(14) -0.1473(14) 0.033(3) Uani 0.467(11) 1 d P A 1
H42A H 0.3368 -0.6506 -0.1118 0.039 Uiso 0.467(11) 1 calc PR A 1
H42B H 0.3597 -0.8058 -0.1445 0.039 Uiso 0.467(11) 1 calc PR A 1
C43A C 0.1640(9) -0.7657(9) -0.0687(9) 0.042(2) Uani 0.467(11) 1 d P A 1
H43A H 0.0984 -0.6949 -0.0646 0.051 Uiso 0.467(11) 1 calc PR A 1
H43B H 0.1041 -0.8518 -0.1155 0.051 Uiso 0.467(11) 1 calc PR A 1
C44A C 0.2317(8) -0.7658(9) 0.0732(9) 0.049(3) Uani 0.467(11) 1 d P A 1
H44A H 0.3186 -0.8155 0.0720 0.058 Uiso 0.467(11) 1 calc PR A 1
H44B H 0.2632 -0.6738 0.1301 0.058 Uiso 0.467(11) 1 calc PR A 1
C45A C 0.117(3) -0.830(3) 0.125(2) 0.095(9) Uani 0.467(11) 1 d P A 1
H45A H 0.0269 -0.7876 0.1132 0.142 Uiso 0.467(11) 1 calc PR A 1
H45B H 0.1508 -0.8207 0.2194 0.142 Uiso 0.467(11) 1 calc PR A 1
H45C H 0.0972 -0.9243 0.0754 0.142 Uiso 0.467(11) 1 calc PR A 1
N41A N 0.218(3) -0.761(3) -0.258(3) 0.043(6) Uani 0.467(11) 1 d P A 1
H41A H 0.1646 -0.8421 -0.2846 0.064 Uiso 0.467(11) 1 calc PR A 1
H41B H 0.2820 -0.7571 -0.3144 0.064 Uiso 0.467(11) 1 calc PR A 1
H41C H 0.1568 -0.6971 -0.2590 0.064 Uiso 0.467(11) 1 calc PR A 1
C42B C 0.306(2) -0.6956(13) -0.1245(17) 0.054(4) Uani 0.533(11) 1 d P A 2
H42C H 0.4032 -0.7297 -0.1151 0.065 Uiso 0.533(11) 1 calc PR A 2
H42D H 0.3266 -0.5991 -0.1120 0.065 Uiso 0.533(11) 1 calc PR A 2
C43B C 0.2447(12) -0.7094(9) -0.0148(8) 0.081(3) Uani 0.533(11) 1 d P A 2
H43C H 0.3277 -0.6849 0.0619 0.097 Uiso 0.533(11) 1 calc PR A 2
H43D H 0.1799 -0.6382 0.0023 0.097 Uiso 0.533(11) 1 calc PR A 2
C44B C 0.1662(11) -0.8201(11) -0.0029(10) 0.083(3) Uani 0.533(11) 1 d P A 2
H44C H 0.2275 -0.8942 -0.0169 0.099 Uiso 0.533(11) 1 calc PR A 2
H44D H 0.0778 -0.8455 -0.0743 0.099 Uiso 0.533(11) 1 calc PR A 2
C45B C 0.1146(15) -0.801(2) 0.1386(19) 0.061(4) Uani 0.533(11) 1 d P A 2
H45D H 0.2014 -0.7798 0.2100 0.091 Uiso 0.533(11) 1 calc PR A 2
H45E H 0.0582 -0.8832 0.1387 0.091 Uiso 0.533(11) 1 calc PR A 2
H45F H 0.0528 -0.7284 0.1533 0.091 Uiso 0.533(11) 1 calc PR A 2
N41B N 0.2238(19) -0.762(3) -0.285(3) 0.025(3) Uani 0.533(11) 1 d P A 2
H41D H 0.1926 -0.8497 -0.2985 0.038 Uiso 0.533(11) 1 calc PR A 2
H41E H 0.2890 -0.7547 -0.3389 0.038 Uiso 0.533(11) 1 calc PR A 2
H41F H 0.1453 -0.7189 -0.3036 0.038 Uiso 0.533(11) 1 calc PR A 2
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'
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
O1A C1 O1B 124.7(2) . .
O1A C1 C2 119.3(2) . .
O1B C1 C2 116.0(2) . .
C3 C2 C1 123.3(2) . .
C3 C2 H2 118.4 . .
C1 C2 H2 118.4 . .
C2 C3 C4 122.8(2) . .
C2 C3 H3 118.6 . .
C4 C3 H3 118.6 . .
O4B C4 O4A 124.2(2) . .
O4B C4 C3 120.5(2) . .
O4A C4 C3 115.3(2) . .
C4 O4A H4 109.5 . .
N21 C22 C23 112.9(2) . .
N21 C22 H22A 109.0 . .
C23 C22 H22A 109.0 . .
N21 C22 H22B 109.0 . .
C23 C22 H22B 109.0 . .
H22A C22 H22B 107.8 . .
C22 C23 C24 111.7(2) . .
C22 C23 H23A 109.3 . .
C24 C23 H23A 109.3 . .
C22 C23 H23B 109.3 . .
C24 C23 H23B 109.3 . .
H23A C23 H23B 107.9 . .
C25 C24 C23 112.9(3) . .
C25 C24 H24A 109.0 . .
C23 C24 H24A 109.0 . .
C25 C24 H24B 109.0 . .
C23 C24 H24B 109.0 . .
H24A C24 H24B 107.8 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C22 N21 H21A 109.5 . .
C22 N21 H21B 109.5 . .
H21A N21 H21B 109.5 . .
C22 N21 H21C 109.5 . .
H21A N21 H21C 109.5 . .
H21B N21 H21C 109.5 . .
O31B C31 O31A 124.9(2) . .
O31B C31 C32 119.7(2) . .
O31A C31 C32 115.4(2) . .
C33 C32 C31 122.5(3) . .
C33 C32 H32 118.8 . .
C31 C32 H32 118.8 . .
C32 C33 C34 123.2(3) . .
C32 C33 H33 118.4 . .
C34 C33 H33 118.4 . .
O34B C34 O34A 125.0(2) . .
O34B C34 C33 121.9(2) . .
O34A C34 C33 113.2(2) . .
C34 O34A H34 109.5 . .
N41A C42A C43A 102.6(17) . .
N41A C42A H42A 111.3 . .
C43A C42A H42A 111.3 . .
N41A C42A H42B 111.3 . .
C43A C42A H42B 111.3 . .
H42A C42A H42B 109.2 . .
C44A C43A C42A 110.6(8) . .
C44A C43A H43A 109.5 . .
C42A C43A H43A 109.5 . .
C44A C43A H43B 109.5 . .
C42A C43A H43B 109.5 . .
H43A C43A H43B 108.1 . .
C45A C44A C43A 106.8(11) . .
C45A C44A H44A 110.4 . .
C43A C44A H44A 110.4 . .
C45A C44A H44B 110.4 . .
C43A C44A H44B 110.4 . .
H44A C44A H44B 108.6 . .
C43B C42B N41B 124.1(15) . .
C43B C42B H42C 106.3 . .
N41B C42B H42C 106.3 . .
C43B C42B H42D 106.3 . .
N41B C42B H42D 106.3 . .
H42C C42B H42D 106.4 . .
C44B C43B C42B 127.8(9) . .
C44B C43B H43C 105.4 . .
C42B C43B H43C 105.4 . .
C44B C43B H43D 105.4 . .
C42B C43B H43D 105.4 . .
H43C C43B H43D 106.0 . .
C43B C44B C45B 114.4(11) . .
C43B C44B H44C 108.7 . .
C45B C44B H44C 108.7 . .
C43B C44B H44D 108.7 . .
C45B C44B H44D 108.7 . .
H44C C44B H44D 107.6 . .
C44B C45B H45D 109.5 . .
C44B C45B H45E 109.5 . .
H45D C45B H45E 109.5 . .
C44B C45B H45F 109.5 . .
H45D C45B H45F 109.5 . .
H45E C45B H45F 109.5 . .
C42B N41B H41D 109.5 . .
C42B N41B H41E 109.5 . .
H41D N41B H41E 109.5 . .
C42B N41B H41F 109.5 . .
H41D N41B H41F 109.5 . .
H41E N41B H41F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1A 1.242(3) .
C1 O1B 1.273(3) .
C1 C2 1.489(3) .
C2 C3 1.319(3) .
C2 H2 0.9500 .
C3 C4 1.483(3) .
C3 H3 0.9500 .
C4 O4B 1.234(3) .
C4 O4A 1.280(3) .
O4A H4 0.8400 .
C22 N21 1.488(3) .
C22 C23 1.494(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.526(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.506(5) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
N21 H21A 0.9100 .
N21 H21B 0.9100 .
N21 H21C 0.9100 .
C31 O31B 1.232(3) .
C31 O31A 1.292(3) .
C31 C32 1.482(3) .
C32 C33 1.319(4) .
C32 H32 0.9500 .
C33 C34 1.479(3) .
C33 H33 0.9500 .
C34 O34B 1.229(3) .
C34 O34A 1.296(3) .
O34A H34 0.8400 .
C42A N41A 1.20(3) .
C42A C43A 1.551(19) .
C42A H42A 0.9900 .
C42A H42B 0.9900 .
C43A C44A 1.535(13) .
C43A H43A 0.9900 .
C43A H43B 0.9900 .
C44A C45A 1.47(2) .
C44A H44A 0.9900 .
C44A H44B 0.9900 .
C45A H45A 0.9800 .
C45A H45B 0.9800 .
C45A H45C 0.9800 .
N41A H41A 0.9100 .
N41A H41B 0.9100 .
N41A H41C 0.9100 .
C42B C43B 1.41(2) .
C42B N41B 1.69(3) .
C42B H42C 0.9900 .
C42B H42D 0.9900 .
C43B C44B 1.376(14) .
C43B H43C 0.9900 .
C43B H43D 0.9900 .
C44B C45B 1.61(2) .
C44B H44C 0.9900 .
C44B H44D 0.9900 .
C45B H45D 0.9800 .
C45B H45E 0.9800 .
C45B H45F 0.9800 .
N41B H41D 0.9100 .
N41B H41E 0.9100 .
N41B H41F 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
N21 H21A O31A 0.91 2.01 2.895(3) 164.8 .
O4A H4 O31A 0.84 1.61 2.453(2) 175.7 2_736
N21 H21B O1A 0.91 1.91 2.802(3) 165.0 2_636
N21 H21C O34B 0.91 1.88 2.783(3) 174.8 2_646
O34A H34 O1B 0.84 1.63 2.457(2) 168.9 2_646
N41A H41A O4B 0.91 1.91 2.81(3) 170.4 1_454
N41A H41C O31B 0.91 1.93 2.82(3) 163.2 1_454
N41B H41D O4B 0.91 1.94 2.83(3) 166.4 1_454
N41B H41F O31B 0.91 1.93 2.822(19) 167.6 1_454
N41A H41B O34A 0.91 2.17 3.00(3) 151.5 2_645
N41B H41E O34A 0.91 1.95 2.78(2) 150.7 2_645
N41A H41B O1A 0.91 2.56 3.09(3) 117.5 1_554
N41B H41E O1A 0.91 2.54 2.98(2) 110.1 1_554
