#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239528.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_2239528
loop_
_publ_author_name
'Maroua, Arbi'
'Lamia, Khederi'
'Ahmed, Hamdi'
'Mohamed, Rzaigui'
_publ_section_title
;
 3-Chloro-2-methylanilinium chloride monohydrate
;
_journal_coeditor_code           FJ2671
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o643
_journal_paper_doi               10.1107/S1600536814009921
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H9 Cl N +, Cl -, H2 O'
_chemical_formula_moiety         'C7 H9 Cl N +, Cl -, H2 O'
_chemical_formula_sum            'C7 H11 Cl2 N O'
_chemical_formula_weight         196.07
_chemical_name_systematic
;
3-Chloro-2-methylanilinium chloride monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.434(4)
_cell_length_b                   7.475(3)
_cell_length_c                   16.785(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     932.7(6)
_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, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            5019
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.421
_refine_ls_abs_structure_details 'Flack (1983), unique data only'
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0547
_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)+(0.0841P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                1804
_reflns_number_total             3947
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2671sup1.cif
_cod_data_source_block           I
_cod_database_code               2239528
_cod_database_fobs_code          2239528
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_thermal_displace_type
_atom_site_occupancy
Cl Cl1 0.21684(13) 0.68978(12) 0.14721(5) 0.0605(3) Uani 1.000
N N1 0.2400(3) 0.3630(3) 0.41835(13) 0.0397(7) Uani 1.000
C C1 0.2542(4) 0.3587(4) 0.33084(16) 0.0375(8) Uani 1.000
C C2 0.2248(4) 0.5163(4) 0.28915(15) 0.0368(7) Uani 1.000
C C3 0.2477(4) 0.5022(5) 0.20642(15) 0.0429(8) Uani 1.000
C C4 0.2959(5) 0.3453(4) 0.16946(19) 0.0520(10) Uani 1.000
C C5 0.3203(5) 0.1946(5) 0.2135(2) 0.0581(10) Uani 1.000
C C6 0.3010(4) 0.2003(4) 0.29557(18) 0.0435(8) Uani 1.000
C C7 0.1793(5) 0.6906(4) 0.3283(2) 0.0551(10) Uani 1.000
O O1W 0.5280(3) 0.0960(3) 0.01902(16) 0.0676(9) Uani 1.000
Cl Cl2 0.62142(10) 0.50337(10) 0.00015(4) 0.0469(2) Uani 1.000
H H1A 0.20910 0.47250 0.43403 0.0477 Uiso 1.000
H H1B 0.34559 0.33388 0.43972 0.0477 Uiso 1.000
H H1C 0.15674 0.28516 0.43419 0.0477 Uiso 1.000
H H3 0.31954 0.09820 0.32617 0.0522 Uiso 1.000
H H4 0.35005 0.08749 0.18857 0.0698 Uiso 1.000
H H5 0.31181 0.34223 0.11452 0.0624 Uiso 1.000
H H7A 0.16524 0.78143 0.28835 0.0825 Uiso 1.000
H H7B 0.27430 0.72387 0.36406 0.0825 Uiso 1.000
H H7C 0.06902 0.67814 0.35757 0.0825 Uiso 1.000
H H1W1 0.42091 0.05452 0.01130 0.0825 Uiso 1.000
H H2W1 0.52857 0.20105 -0.00122 0.0825 Uiso 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 '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
2 -4 1
2 -4 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
H1W1 O1W H2W1 106.00 no
H1A N1 H1C 109.00 no
H1B N1 H1C 109.00 no
C1 N1 H1B 109.00 no
C1 N1 H1C 109.00 no
C1 N1 H1A 109.00 no
H1A N1 H1B 109.00 no
C2 C1 C6 123.8(3) no
N1 C1 C2 118.2(2) no
N1 C1 C6 117.9(3) no
C1 C2 C7 123.6(2) no
C3 C2 C7 121.8(3) no
C1 C2 C3 114.6(3) no
Cl1 C3 C4 117.8(2) no
C2 C3 C4 122.9(3) no
Cl1 C3 C2 119.4(3) no
C3 C4 C5 119.8(3) no
C4 C5 C6 120.1(3) no
C1 C6 C5 118.9(3) no
C3 C4 H5 120.00 no
C5 C4 H5 120.00 no
C6 C5 H4 120.00 no
C4 C5 H4 120.00 no
C1 C6 H3 121.00 no
C5 C6 H3 121.00 no
C2 C7 H7B 109.00 no
C2 C7 H7C 109.00 no
C2 C7 H7A 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
H7A C7 H7B 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.734(4) no
O1W H2W1 0.8600 no
O1W H1W1 0.8600 no
N1 C1 1.473(4) no
N1 H1A 0.8900 no
N1 H1C 0.8900 no
N1 H1B 0.8900 no
C1 C2 1.388(4) no
C1 C6 1.369(4) no
C2 C7 1.498(4) no
C2 C3 1.403(4) no
C3 C4 1.374(5) no
C4 C5 1.360(5) no
C5 C6 1.386(5) no
C4 H5 0.9300 no
C5 H4 0.9300 no
C6 H3 0.9300 no
C7 H7C 0.9600 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
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
O1W H1W1 Cl2 3_455 0.8600 2.2800 3.129(3) 169.00 yes
O1W H2W1 Cl2 . 0.8600 2.3600 3.139(3) 151.00 yes
N1 H1A Cl2 2_565 0.8900 2.7000 3.178(3) 115.00 yes
N1 H1A O1W 4_655 0.8900 2.3000 2.667(4) 105.00 yes
N1 H1B Cl2 4_645 0.8900 2.6800 3.187(3) 117.00 yes
N1 H1B O1W 4_655 0.8900 2.2800 2.667(4) 106.00 yes
N1 H1C Cl2 2_565 0.8900 2.8300 3.178(3) 105.00 yes
C7 H7A Cl1 . 0.9600 2.5000 3.053(4) 117.00 ?
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
_geom_torsion_publ_flag
N1 C1 C2 C3 177.7(3) no
N1 C1 C2 C7 0.2(4) no
C6 C1 C2 C3 -0.3(4) no
C6 C1 C2 C7 -178.0(3) no
N1 C1 C6 C5 -178.1(3) no
C2 C1 C6 C5 -0.2(5) no
C1 C2 C3 Cl1 -179.5(2) no
C1 C2 C3 C4 -0.2(5) no
C7 C2 C3 Cl1 -1.8(4) no
C7 C2 C3 C4 177.6(3) no
Cl1 C3 C4 C5 -179.5(3) no
C2 C3 C4 C5 1.2(5) no
C3 C4 C5 C6 -1.6(5) no
C4 C5 C6 C1 1.1(5) no
