##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-05-14
_journal_date_accepted     2008-05-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o1152
_journal_page_last     o1152
_journal_paper_category     QO
_journal_coeditor_code     LH2629
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Bis(isobutylammonium) phthalate monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Norzalida, Zakaria'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ariffin, Azhar'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(isobutylammonium) phthalate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C4 H12 N +), C8 H4 O4 2-, H2 O'
_chemical_formula_sum     'C16 H30 N2 O5'
_chemical_formula_iupac     '2C4 H12 N +, C8 H4 O4 2-, H2 O'
_chemical_formula_weight     330.42
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.8647(4)
_cell_length_b     9.4340(5)
_cell_length_c     12.9119(6)
_cell_angle_alpha     72.298(3)
_cell_angle_beta     79.449(3)
_cell_angle_gamma     69.059(3)
_cell_volume     957.37(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     941
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     22.7
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.146
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8057
_diffrn_reflns_av_R_equivalents     0.0495
_diffrn_reflns_av_sigmaI/netI     0.0928
_diffrn_reflns_theta_min     2.47
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4343
_reflns_number_gt     2454
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1164
_refine_ls_R_factor_gt     0.0610
_refine_ls_wR_factor_gt     0.1292
_refine_ls_wR_factor_ref     0.1560
_refine_ls_goodness_of_fit_ref     0.973
_refine_ls_restrained_S_all     0.973
_refine_ls_number_reflns     4343
_refine_ls_number_parameters     241
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.329
_refine_diff_density_min     -0.274
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.049(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.49468(17) 0.58257(19) 0.62388(12) 0.0271(4) Uani d . 1 . .
    O O2 0.75147(17) 0.58034(18) 0.58411(12) 0.0250(4) Uani d . 1 . .
    O O3 0.86510(16) 0.23828(19) 0.58460(12) 0.0254(4) Uani d . 1 . .
    O O4 1.08162(16) 0.21636(19) 0.66133(12) 0.0285(4) Uani d . 1 . .
    O O1w 0.7147(2) 0.8989(2) 0.50641(15) 0.0342(4) Uani d D 1 . .
    H H1w1 0.696(3) 0.811(2) 0.535(2) 0.078(12) Uiso d D 1 . .
    H H1w2 0.785(3) 0.887(3) 0.4520(18) 0.096(14) Uiso d D 1 . .
    N N1 0.4142(2) 0.8164(2) 0.43079(16) 0.0230(5) Uani d D 1 . .
    H H1n1 0.448(3) 0.7460(19) 0.4886(14) 0.062(10) Uiso d D 1 . .
    H H1n2 0.3266(18) 0.809(2) 0.4159(16) 0.034(7) Uiso d D 1 . .
    H H1n3 0.391(2) 0.9076(13) 0.4421(17) 0.028(7) Uiso d D 1 . .
    N N2 0.9312(2) 0.4473(3) 0.39672(16) 0.0259(5) Uani d D 1 . .
    H H2n1 0.873(2) 0.5321(15) 0.4154(19) 0.054(9) Uiso d D 1 . .
    H H2n2 1.0323(12) 0.440(2) 0.3961(17) 0.042(8) Uiso d D 1 . .
    H H2n3 0.917(2) 0.3689(16) 0.4499(14) 0.037(8) Uiso d D 1 . .
    C C1 0.6391(3) 0.5332(3) 0.64401(17) 0.0216(5) Uani d . 1 . .
    C C2 0.6832(2) 0.4119(3) 0.75120(17) 0.0212(5) Uani d . 1 . .
    C C3 0.5823(3) 0.4347(3) 0.84480(18) 0.0265(5) Uani d . 1 . .
    H H3 0.4850 0.5215 0.8393 0.032 Uiso calc R 1 . .
    C C4 0.6217(3) 0.3327(3) 0.94606(19) 0.0338(6) Uani d . 1 . .
    H H4 0.5509 0.3489 1.0092 0.041 Uiso calc R 1 . .
    C C5 0.7644(3) 0.2070(3) 0.95501(19) 0.0326(6) Uani d . 1 . .
    H H5 0.7928 0.1378 1.0244 0.039 Uiso calc R 1 . .
    C C6 0.8653(3) 0.1828(3) 0.86233(18) 0.0268(6) Uani d . 1 . .
    H H6 0.9630 0.0964 0.8688 0.032 Uiso calc R 1 . .
    C C7 0.8264(2) 0.2824(3) 0.76022(17) 0.0207(5) Uani d . 1 . .
    C C8 0.9328(2) 0.2442(3) 0.66050(18) 0.0217(5) Uani d . 1 . .
    C C9 0.5386(2) 0.7900(3) 0.33858(17) 0.0231(5) Uani d . 1 . .
    H H9A 0.5535 0.6865 0.3273 0.028 Uiso calc R 1 . .
    H H9B 0.6430 0.7861 0.3584 0.028 Uiso calc R 1 . .
    C C10 0.4971(3) 0.9152(3) 0.23207(19) 0.0309(6) Uani d . 1 . .
    H H10 0.3883 0.9236 0.2148 0.037 Uiso calc R 1 . .
    C C11 0.4909(3) 1.0755(3) 0.2390(2) 0.0464(8) Uani d . 1 . .
    H H11A 0.4091 1.1074 0.2970 0.070 Uiso calc R 1 . .
    H H11B 0.4626 1.1529 0.1692 0.070 Uiso calc R 1 . .
    H H11C 0.5972 1.0693 0.2553 0.070 Uiso calc R 1 . .
    C C12 0.6223(3) 0.8638(3) 0.14157(19) 0.0369(7) Uani d . 1 . .
    H H12A 0.6251 0.7605 0.1383 0.055 Uiso calc R 1 . .
    H H12B 0.7293 0.8575 0.1565 0.055 Uiso calc R 1 . .
    H H12C 0.5931 0.9405 0.0716 0.055 Uiso calc R 1 . .
    C C13 0.8993(3) 0.4525(3) 0.28710(19) 0.0308(6) Uani d . 1 . .
    H H13A 0.9174 0.5469 0.2340 0.037 Uiso calc R 1 . .
    H H13B 0.7845 0.4611 0.2877 0.037 Uiso calc R 1 . .
    C C14 1.0072(3) 0.3079(3) 0.2514(2) 0.0397(7) Uani d . 1 . .
    H H14 1.1214 0.2921 0.2627 0.048 Uiso calc R 1 . .
    C C15 0.9981(5) 0.3334(5) 0.1306(3) 0.0870(13) Uani d . 1 . .
    H H15A 1.0264 0.4277 0.0893 0.130 Uiso calc R 1 . .
    H H15B 0.8878 0.3469 0.1174 0.130 Uiso calc R 1 . .
    H H15C 1.0743 0.2421 0.1069 0.130 Uiso calc R 1 . .
    C C16 0.9674(5) 0.1631(4) 0.3167(3) 0.0663(10) Uani d . 1 . .
    H H16A 0.9732 0.1493 0.3944 0.100 Uiso calc R 1 . .
    H H16B 1.0452 0.0715 0.2941 0.100 Uiso calc R 1 . .
    H H16C 0.8576 0.1736 0.3043 0.100 Uiso calc R 1 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.243(2) ?
    O2 C1 . 1.270(2) ?
    O3 C8 . 1.263(3) ?
    O4 C8 . 1.251(2) ?
    O1w H1w1 . 0.861(10) ?
    O1w H1w2 . 0.858(10) ?
    N1 C9 . 1.483(3) ?
    N1 H1n1 . 0.852(9) ?
    N1 H1n2 . 0.865(9) ?
    N1 H1n3 . 0.861(9) ?
    N2 C13 . 1.477(3) ?
    N2 H2n1 . 0.860(9) ?
    N2 H2n2 . 0.874(9) ?
    N2 H2n3 . 0.873(9) ?
    C1 C2 . 1.514(3) ?
    C2 C3 . 1.389(3) ?
    C2 C7 . 1.406(3) ?
    C3 C4 . 1.386(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.384(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.383(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.386(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.507(3) ?
    C9 C10 . 1.519(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C12 . 1.522(3) ?
    C10 C11 . 1.523(4) ?
    C10 H10 . 1.0000 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.508(4) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C16 . 1.496(4) ?
    C14 C15 . 1.518(4) ?
    C14 H14 . 1.0000 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    H1w1 O1w H1w2 . . 107.2(15) ?
    C9 N1 H1n1 . . 109.2(17) ?
    C9 N1 H1n2 . . 108.1(14) ?
    H1n1 N1 H1n2 . . 109.4(13) ?
    C9 N1 H1n3 . . 113.4(15) ?
    H1n1 N1 H1n3 . . 108.9(13) ?
    H1n2 N1 H1n3 . . 107.9(12) ?
    C13 N2 H2n1 . . 111.6(16) ?
    C13 N2 H2n2 . . 109.3(15) ?
    H2n1 N2 H2n2 . . 106.4(13) ?
    C13 N2 H2n3 . . 116.3(15) ?
    H2n1 N2 H2n3 . . 107.0(13) ?
    H2n2 N2 H2n3 . . 105.7(13) ?
    O1 C1 O2 . . 125.4(2) ?
    O1 C1 C2 . . 117.22(19) ?
    O2 C1 C2 . . 117.30(18) ?
    C3 C2 C7 . . 119.0(2) ?
    C3 C2 C1 . . 118.49(19) ?
    C7 C2 C1 . . 122.38(19) ?
    C4 C3 C2 . . 121.0(2) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 119.9(2) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C6 C5 C4 . . 119.6(2) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    C5 C6 C7 . . 121.2(2) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C6 C7 C2 . . 119.3(2) ?
    C6 C7 C8 . . 119.4(2) ?
    C2 C7 C8 . . 121.22(19) ?
    O4 C8 O3 . . 125.5(2) ?
    O4 C8 C7 . . 117.10(19) ?
    O3 C8 C7 . . 117.40(18) ?
    N1 C9 C10 . . 113.95(18) ?
    N1 C9 H9A . . 108.8 ?
    C10 C9 H9A . . 108.8 ?
    N1 C9 H9B . . 108.8 ?
    C10 C9 H9B . . 108.8 ?
    H9A C9 H9B . . 107.7 ?
    C9 C10 C12 . . 108.7(2) ?
    C9 C10 C11 . . 112.0(2) ?
    C12 C10 C11 . . 110.4(2) ?
    C9 C10 H10 . . 108.5 ?
    C12 C10 H10 . . 108.5 ?
    C11 C10 H10 . . 108.5 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C10 C12 H12A . . 109.5 ?
    C10 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C10 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N2 C13 C14 . . 111.78(19) ?
    N2 C13 H13A . . 109.3 ?
    C14 C13 H13A . . 109.3 ?
    N2 C13 H13B . . 109.3 ?
    C14 C13 H13B . . 109.3 ?
    H13A C13 H13B . . 107.9 ?
    C16 C14 C13 . . 112.4(2) ?
    C16 C14 C15 . . 110.8(3) ?
    C13 C14 C15 . . 110.0(3) ?
    C16 C14 H14 . . 107.8 ?
    C13 C14 H14 . . 107.8 ?
    C15 C14 H14 . . 107.8 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C14 C16 H16A . . 109.5 ?
    C14 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C14 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . -43.9(3) ?
    O2 C1 C2 C3 . . . . 133.5(2) ?
    O1 C1 C2 C7 . . . . 139.7(2) ?
    O2 C1 C2 C7 . . . . -42.9(3) ?
    C7 C2 C3 C4 . . . . 0.4(3) ?
    C1 C2 C3 C4 . . . . -176.1(2) ?
    C2 C3 C4 C5 . . . . 0.8(4) ?
    C3 C4 C5 C6 . . . . -1.1(4) ?
    C4 C5 C6 C7 . . . . 0.1(4) ?
    C5 C6 C7 C2 . . . . 1.2(3) ?
    C5 C6 C7 C8 . . . . -175.0(2) ?
    C3 C2 C7 C6 . . . . -1.4(3) ?
    C1 C2 C7 C6 . . . . 174.98(19) ?
    C3 C2 C7 C8 . . . . 174.7(2) ?
    C1 C2 C7 C8 . . . . -8.9(3) ?
    C6 C7 C8 O4 . . . . -51.4(3) ?
    C2 C7 C8 O4 . . . . 132.5(2) ?
    C6 C7 C8 O3 . . . . 126.5(2) ?
    C2 C7 C8 O3 . . . . -49.7(3) ?
    N1 C9 C10 C12 . . . . -172.76(19) ?
    N1 C9 C10 C11 . . . . 65.0(3) ?
    N2 C13 C14 C16 . . . . 68.6(3) ?
    N2 C13 C14 C15 . . . . -167.4(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1<i>w</i> H1<i>w</i>1 O2 . 0.860(10)
                                        1.97(2) 2.780(2) 156(3) yes
    O1<i>w</i> H1<i>w</i>2 O4 2_766 0.860(10)
                                            1.97(2) 2.780(2) 157(3) yes
    N1 H1<i>n</i>1 O1 . 0.850(10)
                                1.940(10)
                                        2.788(2) 172(2) yes
    N1 H1<i>n</i>2 O3 2_666 0.870(10)
                                    1.910(10)
                                            2.755(2) 167(2) yes
    N1 H1<i>n</i>3 O1<i>w</i> 2_676 0.860(10)
                                            1.990(10)
                                                    2.823(3) 164(2) yes
    N2 H2<i>n</i>1 O2 . 0.860(10)
                                2.35(2) 2.996(2) 132(2) yes
    N2 H2<i>n</i>1 O4 2_766 0.860(10)
                                    2.42(2) 2.995(3) 124(2) yes
    N2 H2<i>n</i>2 O2 2_766 0.870(10)
                                    1.910(10)
                                            2.781(2) 172(2) yes
    N2 H2<i>n</i>3 O3 . 0.870(10)
                                1.890(10)
                                        2.741(2) 166(2) yes
