##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Tetramethylammonium hydrogen 4,5-dichlorophthalate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_sum     'C12 H15 Cl2 N O4'
_chemical_formula_iupac     'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_weight     308.15
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z-1/2'
    'x, -y-1/2, z'
_cell_length_a     10.2800(6)
_cell_length_b     6.9120(3)
_cell_length_c     19.0486(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1353.51(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     18405
_cell_measurement_theta_min     2.14
_cell_measurement_theta_max     27.63
_cell_measurement_temperature     296
_exptl_crystal_description     'rod'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.660
_exptl_crystal_size_mid     0.353
_exptl_crystal_size_min     0.170
_exptl_crystal_density_diffrn     1.512
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.488
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.7834
_exptl_absorpt_correction_T_max     0.9314
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS-2'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     18362
_diffrn_reflns_av_R_equivalents     0.0647
_diffrn_reflns_av_sigmaI/netI     0.0229
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     25.98
_diffrn_reflns_theta_full     25.98
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <2
_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.
;
_reflns_number_total     1449
_reflns_number_gt     1239
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0401
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0919
_refine_ls_wR_factor_ref     0.0954
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     1449
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
   'w = 1/[σ²(Fo²)+1+0.2573P+(0.0562P)²] where P = 0.33Fo² + 0.67Fc²'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.213
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.026(4)
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    C C1 0.4066(2) 0.2500 0.44167(12) 0.0454(5) Uani d S 1 . .
    C C2 0.4771(2) 0.2500 0.50518(11) 0.0450(5) Uani d S 1 . .
    C C3 0.6127(2) 0.2500 0.50158(11) 0.0480(5) Uani d S 1 . .
    H H3 0.6600 0.2500 0.5432 0.058 Uiso calc SR 1 . .
    C C4 0.6796(2) 0.2500 0.43883(12) 0.0479(5) Uani d S 1 . .
    C C5 0.6096(2) 0.2500 0.37654(11) 0.0472(5) Uani d S 1 . .
    C C6 0.4759(2) 0.2500 0.37902(12) 0.0498(5) Uani d S 1 . .
    H H6 0.4299 0.2500 0.3370 0.060 Uiso calc SR 1 . .
    C C7 0.2594(3) 0.2500 0.43061(14) 0.0600(6) Uani d S 1 . .
    C C8 0.4259(3) 0.2500 0.58052(13) 0.0542(6) Uani d S 1 . .
    C C9 0.47041(19) -0.0750(3) 0.20137(11) 0.0650(5) Uani d . 1 . .
    H H9A 0.3859 -0.0740 0.1799 0.097 Uiso calc R 1 . .
    H H9B 0.5176 0.0385 0.1874 0.097 Uiso calc R 1 . .
    H H9C 0.4611 -0.0764 0.2515 0.097 Uiso calc R 1 . .
    C C10 0.6754(2) -0.2500 0.21052(15) 0.0675(8) Uani d S 1 . .
    H H10A 0.6680 -0.2500 0.2608 0.101 Uiso calc SR 1 . .
    H H10B 0.7218 -0.1366 0.1957 0.101 Uiso calc PR 0.50 . .
    H H10C 0.7218 -0.3634 0.1957 0.101 Uiso calc PR 0.50 . .
    C C11 0.5555(3) -0.2500 0.10057(13) 0.0692(8) Uani d S 1 . .
    H H11A 0.4706 -0.2500 0.0796 0.104 Uiso calc SR 1 . .
    H H11B 0.6022 -0.3634 0.0860 0.104 Uiso calc PR 0.50 . .
    H H11C 0.6022 -0.1366 0.0860 0.104 Uiso calc PR 0.50 . .
    N N1 0.54249(17) -0.2500 0.17855(10) 0.0487(5) Uani d S 1 . .
    O O1 0.2171(2) 0.2500 0.37122(12) 0.0946(8) Uani d S 1 . .
    O O2 0.1854(2) 0.2500 0.48320(13) 0.1022(9) Uani d S 1 . .
    O O3 0.3031(2) 0.2500 0.59080(11) 0.0791(6) Uani d S 1 . .
    O O4 0.5034(2) 0.2500 0.62873(9) 0.0729(6) Uani d S 1 . .
    Cl Cl1 0.84719(6) 0.2500 0.43804(3) 0.0661(3) Uani d S 1 . .
    Cl Cl2 0.68740(6) 0.2500 0.29635(3) 0.0611(2) Uani d S 1 . .
    H H3A 0.242(5) 0.2500 0.538(3) 0.129(14) Uiso d S 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0445(12) 0.0447(11) 0.0469(12) 0.000 -0.0013(9) 0.000
    C2 0.0503(12) 0.0434(11) 0.0414(11) 0.000 0.0022(9) 0.000
    C3 0.0484(12) 0.0561(13) 0.0394(11) 0.000 -0.0044(9) 0.000
    C4 0.0455(12) 0.0566(13) 0.0416(11) 0.000 -0.0020(9) 0.000
    C5 0.0491(12) 0.0525(13) 0.0399(11) 0.000 -0.0002(9) 0.000
    C6 0.0501(12) 0.0566(14) 0.0425(11) 0.000 -0.0045(10) 0.000
    C7 0.0470(13) 0.0705(17) 0.0626(15) 0.000 0.0000(12) 0.000
    C8 0.0616(15) 0.0556(14) 0.0454(12) 0.000 0.0078(11) 0.000
    C9 0.0577(10) 0.0730(12) 0.0643(10) 0.0082(9) 0.0015(8) -0.0009(10)
    C10 0.0385(12) 0.101(2) 0.0633(16) 0.000 -0.0120(11) 0.000
    C11 0.0581(15) 0.108(2) 0.0413(13) 0.000 -0.0002(11) 0.000
    N1 0.0348(9) 0.0706(13) 0.0406(10) 0.000 -0.0011(7) 0.000
    O1 0.0528(11) 0.168(3) 0.0633(13) 0.000 -0.0128(10) 0.000
    O2 0.0483(11) 0.189(3) 0.0694(14) 0.000 0.0080(10) 0.000
    O3 0.0602(11) 0.1206(18) 0.0566(12) 0.000 0.0159(9) 0.000
    O4 0.0784(13) 0.0997(15) 0.0405(9) 0.000 0.0027(9) 0.000
    Cl1 0.0449(3) 0.1033(6) 0.0501(4) 0.000 -0.0013(2) 0.000
    Cl2 0.0567(4) 0.0860(5) 0.0405(3) 0.000 0.0038(2) 0.000
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.390(3) ?
    C1 C2 . 1.410(3) y
    C1 C7 . 1.528(3) y
    C2 C3 . 1.396(3) ?
    C2 C8 . 1.529(3) y
    C3 C4 . 1.379(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.388(3) ?
    C4 Cl1 . 1.722(2) ?
    C5 C6 . 1.375(3) ?
    C5 Cl2 . 1.724(2) ?
    C6 H6 . 0.9300 ?
    C7 O1 . 1.212(3) y
    C7 O2 . 1.258(3) y
    C8 O4 . 1.215(3) y
    C8 O3 . 1.278(3) y
    C9 N1 . 1.483(2) y
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 N1 . 1.496(3) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 N1 . 1.491(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    N1 C9 8 1.483(2) ?
    O2 H3A . 1.20(5) ?
    O3 H3A . 1.18(5) ?
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
    C6 C1 C2 . . 118.2(2) ?
    C6 C1 C7 . . 112.9(2) ?
    C2 C1 C7 . . 128.9(2) ?
    C3 C2 C1 . . 118.1(2) ?
    C3 C2 C8 . . 113.0(2) ?
    C1 C2 C8 . . 128.9(2) ?
    C4 C3 C2 . . 122.7(2) ?
    C4 C3 H3 . . 118.6 ?
    C2 C3 H3 . . 118.6 ?
    C3 C4 C5 . . 118.8(2) ?
    C3 C4 Cl1 . . 120.41(17) ?
    C5 C4 Cl1 . . 120.75(18) ?
    C6 C5 C4 . . 119.3(2) ?
    C6 C5 Cl2 . . 119.61(17) ?
    C4 C5 Cl2 . . 121.11(18) ?
    C5 C6 C1 . . 122.8(2) ?
    C5 C6 H6 . . 118.6 ?
    C1 C6 H6 . . 118.6 ?
    O1 C7 O2 . . 121.7(3) ?
    O1 C7 C1 . . 119.0(2) ?
    O2 C7 C1 . . 119.3(2) ?
    O4 C8 O3 . . 122.1(2) ?
    O4 C8 C2 . . 118.9(2) ?
    O3 C8 C2 . . 119.0(2) ?
    N1 C9 H9A . . 109.5 ?
    N1 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    N1 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N1 C10 H10A . . 109.5 ?
    N1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N1 C11 H11A . . 109.5 ?
    N1 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N1 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C9 N1 C9 8 . 109.2(2) y
    C9 N1 C11 8 . 109.68(13) y
    C9 N1 C11 . . 109.68(13) ?
    C9 N1 C10 8 . 109.69(13) y
    C9 N1 C10 . . 109.69(13) ?
    C11 N1 C10 . . 108.86(19) y
    C7 O2 H3A . . 114(2) ?
    C8 O3 H3A . . 113(2) ?
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
    C6 C1 C2 C3 . . . . 0.0 ?
    C7 C1 C2 C3 . . . . 180.0 ?
    C6 C1 C2 C8 . . . . 180.0 ?
    C7 C1 C2 C8 . . . . 0.0 ?
    C1 C2 C3 C4 . . . . 0.0 ?
    C8 C2 C3 C4 . . . . 180.0 ?
    C2 C3 C4 C5 . . . . 0.0 ?
    C2 C3 C4 Cl1 . . . . 180.0 ?
    C3 C4 C5 C6 . . . . 0.0 ?
    Cl1 C4 C5 C6 . . . . 180.0 ?
    C3 C4 C5 Cl2 . . . . 180.0 ?
    Cl1 C4 C5 Cl2 . . . . 0.0 ?
    C4 C5 C6 C1 . . . . 0.0 ?
    Cl2 C5 C6 C1 . . . . 180.0 ?
    C2 C1 C6 C5 . . . . 0.0 ?
    C7 C1 C6 C5 . . . . 180.0 ?
    C6 C1 C7 O1 . . . . 0.0 y
    C2 C1 C7 O1 . . . . 180.0 ?
    C6 C1 C7 O2 . . . . 180.0 ?
    C2 C1 C7 O2 . . . . 0.0 ?
    C3 C2 C8 O4 . . . . 0.0 y
    C1 C2 C8 O4 . . . . 180.0 ?
    C3 C2 C8 O3 . . . . 180.0 ?
    C1 C2 C8 O3 . . . . 0.0 ?
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
    O2 H3A O3 . 1.18(5) 1.20(5) 2.380(3) 177(4)
    C11 H11A O2 2_554 0.96 2.44 3.337(3) 155.8
    C11 H11A O3 2_554 0.96 2.82 3.691(3) 151.0
    C10 H10A O4 5_656 0.96 2.75 3.571(4) 144.6
    C9 H9C O4 5_656 0.96 2.60 3.466(3) 149.6
    C9 H9B O1 6_656 0.96 2.76 3.659(3) 157.2
data_global
_journal_date_recd_electronic     2006-08-25
_journal_date_accepted     2006-08-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4258
_journal_page_last     o4260
_journal_paper_category     EO
_journal_coeditor_code     AT2096
_publ_contact_author
;
   Mustafa Odabaşoğlu
    Department of Chemistry
    Faculty of Arts & Science
    Ondokuz Mayıs University
    55139 Kurupelit Samsun
    Turkey
;
_publ_contact_author_email     muodabas@omu.edu.tr
_publ_contact_author_fax     '++90(362) 457 6081'
_publ_contact_author_phone     '++90(362) 312 1919 ext. 5196'
_publ_section_title
;
Tetramethylammonium hydrogen 4,5-dichlorophthalate
;
loop_
    _publ_author_name
    _publ_author_address
    'Bozkurt, Esat'
;
    Department of Physics
    Faculty of Arts & Science
    Ondokuz Mayıs University
    TR-55139 Kurupelit Samsun
    Turkey
;
    'Kartal, İbrahim'
;
    Department of Physics
    Faculty of Arts & Science
    Ondokuz Mayıs University
    TR-55139 Kurupelit Samsun
    Turkey
;
    'Odabaşoğlu, Mustafa'
;
    Department of Chemistry
    Faculty of Arts & Science
    Ondokuz Mayıs University
    TR-55139 Kurupelit Samsun
    Turkey
;
    'Büyükgüngör, Orhan'
;   Department of Physics
    Faculty of Arts & Science
    Ondokuz Mayıs University
    TR-55139 Kurupelit Samsun
    Turkey
;
