##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,4,6-Trimethylanilinium chloroacetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H14 N +, C2 H2 Cl O2 -'
_chemical_formula_sum     'C11 H16 Cl N O2'
_chemical_formula_iupac     'C9 H14 N +, C2 H2 Cl O2 -'
_chemical_formula_weight     229.70
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     26.529(5)
_cell_length_b     4.7453(9)
_cell_length_c     22.717(5)
_cell_angle_alpha     90.00
_cell_angle_beta     124.24(3)
_cell_angle_gamma     90.00
_cell_volume     2364.2(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2690
_cell_measurement_theta_min     3.07
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.2000
_exptl_crystal_size_mid     0.2000
_exptl_crystal_size_min     0.2000
_exptl_crystal_density_diffrn     1.291
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.304
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.941
_exptl_absorpt_correction_T_max     0.941
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Rigaku SCXmini'
_diffrn_measurement_method     'CCD_Profile_fitting'
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     11449
_diffrn_reflns_av_R_equivalents     0.0504
_diffrn_reflns_av_sigmaI/netI     0.0424
_diffrn_reflns_theta_min     3.07
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -34
_diffrn_reflns_limit_h_max     34
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     2690
_reflns_number_gt     1900
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0843
_refine_ls_R_factor_gt     0.0565
_refine_ls_wR_factor_gt     0.1542
_refine_ls_wR_factor_ref     0.1794
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     2690
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0913P)²+1.3591P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.302
_refine_diff_density_min     -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material     'SHELXL97 (Sheldrick, 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.24425(10) -0.0238(5) 0.67051(12) 0.0389(6) Uani d . 1 1 . .
    H H1 0.2600 -0.1541 0.7074 0.047 Uiso calc R 1 1 . .
    C C2 0.28257(11) 0.0902(5) 0.65328(12) 0.0396(6) Uani d . 1 1 . .
    C C3 0.25819(11) 0.2862(5) 0.59771(13) 0.0383(5) Uani d . 1 1 . .
    H H3 0.2835 0.3641 0.5858 0.046 Uiso calc R 1 1 . .
    C C4 0.19732(10) 0.3681(5) 0.55975(12) 0.0331(5) Uani d . 1 1 . .
    C C5 0.16059(9) 0.2490(4) 0.57926(11) 0.0298(5) Uani d . 1 1 . .
    C C6 0.18307(10) 0.0510(5) 0.63429(11) 0.0327(5) Uani d . 1 1 . .
    C C7 0.17409(12) 0.5789(5) 0.49986(13) 0.0431(6) Uani d . 1 1 . .
    H H7A 0.1644 0.7526 0.5130 0.065 Uiso calc R 1 1 . .
    H H7B 0.1382 0.5055 0.4576 0.065 Uiso calc R 1 1 . .
    H H7C 0.2050 0.6122 0.4910 0.065 Uiso calc R 1 1 . .
    C C8 0.14313(11) -0.0861(6) 0.65436(14) 0.0449(6) Uani d . 1 1 . .
    H H8A 0.1633 -0.2502 0.6829 0.067 Uiso calc R 1 1 . .
    H H8B 0.1050 -0.1400 0.6119 0.067 Uiso calc R 1 1 . .
    H H8C 0.1359 0.0450 0.6810 0.067 Uiso calc R 1 1 . .
    C C9 0.34835(12) -0.0022(7) 0.69235(15) 0.0559(7) Uani d . 1 1 . .
    H H9A 0.3648 -0.0243 0.7420 0.084 Uiso calc R 1 1 . .
    H H9B 0.3714 0.1375 0.6866 0.084 Uiso calc R 1 1 . .
    H H9C 0.3506 -0.1786 0.6733 0.084 Uiso calc R 1 1 . .
    C C10 -0.00154(10) 0.7701(5) 0.40030(12) 0.0354(5) Uani d . 1 1 . .
    C C11 -0.00622(14) 0.9110(8) 0.33770(15) 0.0690(10) Uani d . 1 1 . .
    H H11A -0.0403 1.0412 0.3163 0.083 Uiso calc R 1 1 . .
    H H11B -0.0156 0.7677 0.3025 0.083 Uiso calc R 1 1 . .
    Cl Cl1 0.05862(4) 1.0959(2) 0.35657(5) 0.0832(4) Uani d . 1 1 . .
    N N1 0.09497(8) 0.3181(4) 0.53843(9) 0.0328(4) Uani d . 1 1 . .
    H H1A 0.0737 0.1818 0.5070 0.049 Uiso calc R 1 1 . .
    H H1B 0.0884 0.4804 0.5155 0.049 Uiso calc R 1 1 . .
    H H1C 0.0833 0.3337 0.5681 0.049 Uiso calc R 1 1 . .
    O O1 -0.04344(8) 0.6016(4) 0.38346(10) 0.0499(5) Uani d . 1 1 . .
    O O2 0.04153(8) 0.8320(3) 0.46255(8) 0.0432(4) Uani d . 1 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 0.0366(13) 0.0421(13) 0.0342(12) 0.0037(10) 0.0175(11) 0.0028(10)
    C2 0.0326(12) 0.0467(14) 0.0370(12) 0.0019(10) 0.0181(11) -0.0029(10)
    C3 0.0349(12) 0.0410(13) 0.0456(13) -0.0045(10) 0.0267(11) -0.0033(10)
    C4 0.0356(12) 0.0296(11) 0.0353(11) -0.0024(9) 0.0207(10) -0.0051(9)
    C5 0.0284(11) 0.0288(11) 0.0305(11) -0.0029(8) 0.0157(9) -0.0051(8)
    C6 0.0342(12) 0.0333(12) 0.0302(11) -0.0033(9) 0.0180(10) -0.0029(9)
    C7 0.0471(14) 0.0406(14) 0.0472(14) -0.0001(11) 0.0300(13) 0.0063(11)
    C8 0.0419(14) 0.0473(15) 0.0459(14) 0.0015(11) 0.0251(12) 0.0124(11)
    C9 0.0353(14) 0.078(2) 0.0488(16) 0.0087(13) 0.0205(13) 0.0064(14)
    C10 0.0319(12) 0.0367(13) 0.0380(12) 0.0007(9) 0.0198(11) 0.0001(10)
    C11 0.0509(17) 0.103(3) 0.0427(16) -0.0298(17) 0.0204(14) 0.0072(15)
    Cl1 0.0700(6) 0.1098(8) 0.0800(6) -0.0347(5) 0.0484(5) 0.0061(5)
    N1 0.0304(10) 0.0319(10) 0.0351(10) -0.0026(8) 0.0179(8) -0.0005(8)
    O1 0.0449(10) 0.0583(12) 0.0523(11) -0.0175(9) 0.0308(9) -0.0082(9)
    O2 0.0433(10) 0.0368(9) 0.0354(9) -0.0011(7) 0.0136(8) 0.0001(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C2 . 1.388(3) ?
    C1 C6 . 1.391(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.399(3) ?
    C2 C9 . 1.511(3) ?
    C3 C4 . 1.391(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.397(3) ?
    C4 C7 . 1.512(3) ?
    C5 C6 . 1.401(3) ?
    C5 N1 . 1.477(3) ?
    C6 C8 . 1.516(3) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 O1 . 1.242(3) ?
    C10 O2 . 1.254(3) ?
    C10 C11 . 1.512(4) ?
    C11 Cl1 . 1.756(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    N1 H1A . 0.8900 ?
    N1 H1B . 0.8900 ?
    N1 H1C . 0.8900 ?
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
    C2 C1 C6 . . 122.0(2) ?
    C2 C1 H1 . . 119.0 ?
    C6 C1 H1 . . 119.0 ?
    C1 C2 C3 . . 118.2(2) ?
    C1 C2 C9 . . 120.5(2) ?
    C3 C2 C9 . . 121.2(2) ?
    C4 C3 C2 . . 122.1(2) ?
    C4 C3 H3 . . 119.0 ?
    C2 C3 H3 . . 119.0 ?
    C3 C4 C5 . . 117.6(2) ?
    C3 C4 C7 . . 119.1(2) ?
    C5 C4 C7 . . 123.3(2) ?
    C4 C5 C6 . . 122.1(2) ?
    C4 C5 N1 . . 119.81(19) ?
    C6 C5 N1 . . 117.96(18) ?
    C1 C6 C5 . . 117.9(2) ?
    C1 C6 C8 . . 119.5(2) ?
    C5 C6 C8 . . 122.5(2) ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C6 C8 H8A . . 109.5 ?
    C6 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C6 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O1 C10 O2 . . 126.0(2) ?
    O1 C10 C11 . . 114.2(2) ?
    O2 C10 C11 . . 119.8(2) ?
    C10 C11 Cl1 . . 116.1(2) ?
    C10 C11 H11A . . 108.3 ?
    Cl1 C11 H11A . . 108.3 ?
    C10 C11 H11B . . 108.3 ?
    Cl1 C11 H11B . . 108.3 ?
    H11A C11 H11B . . 107.4 ?
    C5 N1 H1A . . 109.5 ?
    C5 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C5 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
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
    N1 H1B O2 . 0.89 2.02 2.860(2) 156
    N1 H1A O2 1_545 0.89 1.88 2.748(2) 165
    N1 H1C O1 5_566 0.89 1.93 2.809(2) 169
data_global
_journal_date_recd_electronic     2011-07-03
_journal_date_accepted     2011-07-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o1997
_journal_page_last     o1997
_journal_paper_category     QO
_journal_coeditor_code     JH2308
_publ_contact_author_name     'Tao, Rong'
_publ_contact_author_address
;
Ordered Matter Science Research Center, Southeast UniVersity,
Nanjing 210096, People's Republic of China
;
_publ_contact_author_email     'rongtao198806@163.com'
_publ_contact_author_fax     '86-25-52090626'
_publ_contact_author_phone     '86-25-52090626'
_publ_section_title
;
2,4,6-Trimethylanilinium chloroacetate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tao, Rong' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 210096, People's Republic of China
;
