#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220207.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220207
loop_
_publ_author_name
'Smirani, Wajda'
'Amri, Olfa'
'Rzaigui, Mohamed'
_publ_section_title
;
 2,6-Dimethylanilinium chloride monohydrate
;
_journal_coeditor_code           HB2860
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2463
_journal_paper_doi               10.1107/S1600536808039159
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H12 N +, Cl -, H2 O'
_chemical_formula_moiety         'C8 H12 N +, Cl -, H2 O'
_chemical_formula_sum            'C8 H14 Cl N O'
_chemical_formula_weight         175.65
_chemical_name_common            '2,6-xylidinium chloride monohydrate'
_chemical_name_systematic
;
2,6-Dimethylanilinium chloride monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.88(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.676(3)
_cell_length_b                   14.144(3)
_cell_length_c                   7.913(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.81
_cell_measurement_theta_min      9.21
_cell_volume                     950.2(8)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'Non-profiled ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3722
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0307
_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)+(0.0408P)²+0.1063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1827
_reflns_number_total             2244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2860.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220207
_cod_database_fobs_code          2220207
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
H H8 0.3326(19) 0.0879(11) 0.050(2) 0.048(4) Uiso d 1
H H7 0.3721(19) 0.1013(11) 0.233(2) 0.045(4) Uiso d 1
H H5 -0.159(2) 0.2065(13) 0.033(2) 0.058(4) Uiso d 1
H H6 0.3494(19) 0.0085(13) 0.161(2) 0.053(4) Uiso d 1
H H3 -0.121(2) -0.0291(12) 0.318(2) 0.055(4) Uiso d 1
H H13 0.171(2) 0.2037(14) -0.109(2) 0.066(5) Uiso d 1
H H11 0.265(2) -0.0493(14) 0.427(3) 0.070(6) Uiso d 1
H H17 0.056(2) 0.2698(15) -0.066(2) 0.073(5) Uiso d 1
H H2 0.488(3) 0.2297(19) 0.405(3) 0.083(7) Uiso d 1
H H4 -0.278(2) 0.0943(13) 0.191(2) 0.067(5) Uiso d 1
H H1 0.472(3) 0.1562(17) 0.518(3) 0.090(7) Uiso d 1
H H10 0.215(2) -0.1099(13) 0.268(2) 0.062(5) Uiso d 1
H H9 0.124(2) -0.1045(14) 0.406(3) 0.071(6) Uiso d 1
H H12 0.215(3) 0.2560(15) 0.065(3) 0.087(7) Uiso d 1
N N1 0.31170(12) 0.06739(8) 0.14878(14) 0.0353(2) Uani d 1
C C7 0.1308(2) 0.22609(11) -0.0155(2) 0.0510(3) Uani d 1
C C8 0.1800(2) -0.07172(12) 0.3454(2) 0.0512(3) Uani d 1
C C1 0.14475(13) 0.07516(8) 0.15925(14) 0.0322(2) Uani d 1
C C6 0.05793(14) 0.15126(9) 0.07822(14) 0.0359(3) Uani d 1
C C5 -0.09996(16) 0.15637(10) 0.08975(17) 0.0435(3) Uani d 1
C C2 0.08245(14) 0.00745(9) 0.25368(15) 0.0367(3) Uani d 1
C C3 -0.07586(16) 0.01607(10) 0.26089(17) 0.0445(3) Uani d 1
C C4 -0.16594(15) 0.08936(11) 0.18003(18) 0.0466(3) Uani d 1
O O1 0.48995(14) 0.16863(9) 0.41224(15) 0.0580(3) Uani d 1
Cl Cl1 0.45854(4) 0.11499(2) 0.81025(4) 0.04716(12) Uani d 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
N1 0.0319(5) 0.0398(5) 0.0364(5) 0.0052(4) 0.0125(4) 0.0025(4)
C7 0.0553(9) 0.0467(7) 0.0546(8) 0.0130(7) 0.0200(7) 0.0119(6)
C8 0.0580(9) 0.0523(8) 0.0493(8) 0.0100(7) 0.0253(7) 0.0123(7)
C1 0.0282(5) 0.0398(6) 0.0296(5) 0.0024(4) 0.0083(4) -0.0058(4)
C6 0.0370(6) 0.0389(6) 0.0318(5) 0.0050(5) 0.0074(4) -0.0049(4)
C5 0.0356(6) 0.0504(7) 0.0428(6) 0.0102(6) 0.0039(5) -0.0091(6)
C2 0.0378(6) 0.0416(6) 0.0328(5) 0.0007(5) 0.0121(4) -0.0047(5)
C3 0.0402(7) 0.0524(8) 0.0452(6) -0.0068(6) 0.0186(5) -0.0077(6)
C4 0.0298(6) 0.0602(8) 0.0508(7) -0.0003(5) 0.0107(5) -0.0145(6)
O1 0.0654(7) 0.0543(7) 0.0509(6) 0.0072(5) 0.0039(5) -0.0041(5)
Cl1 0.04621(19) 0.04719(19) 0.0534(2) 0.01013(14) 0.02267(14) 0.00643(13)
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'
Cl Cl 0.1484 0.1585 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -5 -3
1 5 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 H8 114.1(10)
C1 N1 H7 110.5(10)
H8 N1 H7 106.5(15)
C1 N1 H6 114.0(11)
H8 N1 H6 105.3(15)
H7 N1 H6 105.9(14)
C6 C7 H13 114.5(12)
C6 C7 H17 110.9(13)
H13 C7 H17 103.3(16)
C6 C7 H12 108.9(13)
H13 C7 H12 108.2(18)
H17 C7 H12 111.0(18)
C2 C8 H11 111.7(12)
C2 C8 H10 110.5(11)
H11 C8 H10 109.9(17)
C2 C8 H9 109.7(13)
H11 C8 H9 104.3(18)
H10 C8 H9 110.5(17)
C2 C1 C6 123.14(11)
C2 C1 N1 118.34(11)
C6 C1 N1 118.50(11)
C1 C6 C5 117.13(12)
C1 C6 C7 121.91(11)
C5 C6 C7 120.95(12)
C4 C5 C6 121.09(13)
C4 C5 H5 121.5(11)
C6 C5 H5 117.4(11)
C1 C2 C3 117.24(12)
C1 C2 C8 122.14(12)
C3 C2 C8 120.62(12)
C4 C3 C2 121.22(13)
C4 C3 H3 119.6(11)
C2 C3 H3 119.2(11)
C3 C4 C5 120.15(12)
C3 C4 H4 118.9(11)
C5 C4 H4 120.9(11)
H2 O1 H1 105(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4718(16)
N1 H8 0.883(18)
N1 H7 0.896(17)
N1 H6 0.893(18)
C7 C6 1.504(2)
C7 H13 0.93(2)
C7 H17 0.92(2)
C7 H12 0.96(2)
C8 C2 1.498(2)
C8 H11 0.93(2)
C8 H10 0.92(2)
C8 H9 0.88(2)
C1 C2 1.3907(17)
C1 C6 1.3921(17)
C6 C5 1.3934(18)
C5 C4 1.380(2)
C5 H5 0.935(18)
C2 C3 1.3917(18)
C3 C4 1.374(2)
C3 H3 0.918(18)
C4 H4 1.00(2)
O1 H2 0.87(3)
O1 H1 0.90(3)
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 H1 Cl1 . 0.90(2) 2.41(2) 3.305(3) 173(2) yes
O1 H2 Cl1 4_565 0.87(3) 2.32(3) 3.163(3) 165(2) yes
N1 H6 Cl1 3_656 0.893(18) 2.392(18) 3.235(3) 157.5(15) yes
N1 H7 O1 . 0.896(16) 1.835(16) 2.731(3) 177.3(17) yes
N1 H8 Cl1 1_554 0.883(16) 2.414(16) 3.265(3) 162.8(15) yes
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
C2 C1 C6 C5 -2.12(17)
N1 C1 C6 C5 179.69(10)
C2 C1 C6 C7 176.85(12)
N1 C1 C6 C7 -1.34(17)
C1 C6 C5 C4 0.94(17)
C7 C6 C5 C4 -178.04(13)
C6 C1 C2 C3 2.13(17)
N1 C1 C2 C3 -179.68(10)
C6 C1 C2 C8 -177.60(12)
N1 C1 C2 C8 0.60(18)
C1 C2 C3 C4 -0.96(18)
C8 C2 C3 C4 178.78(14)
C2 C3 C4 C5 -0.1(2)
C6 C5 C4 C3 0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655664
