#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/25/2232575.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_2232575
loop_
_publ_author_name
'Hossein Zadeh, Soudeh'
'Talei Bavil Olyai, Mohamad Reza'
'Biglari Mazlaghani, Hossein'
'Notash, Behrouz'
_publ_section_title
;
 A second monoclinic polymorph of 2,4-dimethylanilinium chloride
;
_journal_coeditor_code           BT5679
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3190
_journal_paper_doi               10.1107/S160053681104551X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H12 N +, Cl -'
_chemical_formula_moiety         'C8 H12 N +, Cl -'
_chemical_formula_sum            'C8 H12 Cl N'
_chemical_formula_weight         157.64
_chemical_name_systematic
;
2,4-dimethylanilinium chloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3651(11)
_cell_length_b                   18.631(4)
_cell_length_c                   8.5428(17)
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.19
_cell_volume                     851.3(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_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      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5557
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0422
_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)+(0.0462P)²+0.1562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                1838
_reflns_number_total             2276
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5679.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2232575
_cod_database_fobs_code          2232575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C8 0.9245(5) 0.39088(11) 0.1976(3) 0.0692(6) Uani d . 1 1
H H8A 1.0616 0.3635 0.2452 0.104 Uiso calc R 1 1
H H8B 0.9148 0.3842 0.0858 0.104 Uiso calc R 1 1
H H8C 0.7715 0.3750 0.2376 0.104 Uiso calc R 1 1
C C7 0.6327(3) 0.64679(10) 0.1382(2) 0.0533(4) Uani d . 1 1
H H7A 0.6040 0.6834 0.2139 0.080 Uiso calc R 1 1
H H7B 0.4783 0.6227 0.1078 0.080 Uiso calc R 1 1
H H7C 0.6969 0.6683 0.0475 0.080 Uiso calc R 1 1
Cl Cl1 0.08615(7) 0.78443(2) 0.04928(5) 0.04796(14) Uani d . 1 1
N N1 1.0561(3) 0.68899(8) 0.35343(16) 0.0406(3) Uani d . 1 1
C C1 1.0245(3) 0.61337(8) 0.30934(16) 0.0367(3) Uani d . 1 1
C C2 0.8198(3) 0.59328(9) 0.20976(17) 0.0407(3) Uani d . 1 1
C C3 0.7952(3) 0.52034(10) 0.17611(19) 0.0477(4) Uani d . 1 1
H H3 0.6585 0.5053 0.1107 0.057 Uiso calc R 1 1
C C5 1.1683(3) 0.49210(10) 0.3321(2) 0.0502(4) Uani d . 1 1
H H5 1.2861 0.4589 0.3719 0.060 Uiso calc R 1 1
C C4 0.9645(3) 0.46926(9) 0.23530(19) 0.0478(4) Uani d . 1 1
C C6 1.1980(3) 0.56416(9) 0.37005(19) 0.0458(4) Uani d . 1 1
H H6 1.3341 0.5792 0.4360 0.055 Uiso calc R 1 1
H H1A 0.932(4) 0.7056(11) 0.411(3) 0.057(6) Uiso d . 1 1
H H1C 1.060(4) 0.7208(11) 0.268(3) 0.062(6) Uiso d . 1 1
H H1B 1.192(5) 0.6971(11) 0.415(2) 0.057(6) Uiso 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
C8 0.0840(16) 0.0542(12) 0.0681(12) 0.0007(11) -0.0025(11) -0.0061(9)
C7 0.0395(9) 0.0614(11) 0.0569(10) 0.0008(8) -0.0108(7) 0.0054(8)
Cl1 0.0356(2) 0.0578(3) 0.0501(2) -0.00034(18) 0.00128(14) 0.01375(18)
N1 0.0323(7) 0.0494(8) 0.0397(7) -0.0023(6) 0.0003(5) 0.0018(6)
C1 0.0299(7) 0.0462(8) 0.0342(6) -0.0031(6) 0.0036(5) 0.0034(6)
C2 0.0325(7) 0.0526(9) 0.0366(7) -0.0016(7) 0.0001(5) 0.0035(6)
C3 0.0437(9) 0.0567(10) 0.0415(8) -0.0067(7) -0.0051(6) -0.0019(7)
C5 0.0442(9) 0.0532(10) 0.0525(9) 0.0065(8) -0.0007(7) 0.0080(7)
C4 0.0530(10) 0.0499(9) 0.0406(8) -0.0012(8) 0.0048(7) 0.0010(7)
C6 0.0345(8) 0.0553(10) 0.0462(8) -0.0017(7) -0.0056(6) 0.0062(7)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C1 N1 H1A 112.9(13)
C1 N1 H1C 114.4(12)
H1A N1 H1C 105.4(18)
C1 N1 H1B 113.2(13)
H1A N1 H1B 103.1(18)
H1C N1 H1B 106.9(18)
C6 C1 C2 122.02(15)
C6 C1 N1 118.79(14)
C2 C1 N1 119.18(14)
C1 C2 C3 116.57(15)
C1 C2 C7 122.66(15)
C3 C2 C7 120.76(15)
C4 C3 C2 123.15(16)
C4 C3 H3 118.4
C2 C3 H3 118.4
C4 C5 C6 120.51(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C3 C4 C5 118.14(16)
C3 C4 C8 120.66(17)
C5 C4 C8 121.19(18)
C1 C6 C5 119.59(15)
C1 C6 H6 120.2
C5 C6 H6 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 C4 1.507(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C7 C2 1.509(2)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N1 C1 1.465(2)
N1 H1A 0.91(2)
N1 H1C 0.94(2)
N1 H1B 0.88(2)
C1 C6 1.379(2)
C1 C2 1.387(2)
C2 C3 1.393(2)
C3 C4 1.383(2)
C3 H3 0.9300
C5 C4 1.385(3)
C5 C6 1.387(3)
C5 H5 0.9300
C6 H6 0.9300
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 H1A Cl1 4_676 0.91(2) 2.28(2) 3.1721(17) 164.4(17)
N1 H1B Cl1 4_776 0.88(2) 2.35(2) 3.2228(17) 172.1(18)
N1 H1C Cl1 1_655 0.94(2) 2.23(2) 3.1630(16) 172.8(19)
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
C6 C1 C2 C3 1.2(2)
N1 C1 C2 C3 -177.97(14)
C6 C1 C2 C7 -178.00(15)
N1 C1 C2 C7 2.9(2)
C1 C2 C3 C4 -0.8(2)
C7 C2 C3 C4 178.37(15)
C2 C3 C4 C5 -0.3(2)
C2 C3 C4 C8 178.59(17)
C6 C5 C4 C3 1.1(2)
C6 C5 C4 C8 -177.79(17)
C2 C1 C6 C5 -0.4(2)
N1 C1 C6 C5 178.72(15)
C4 C5 C6 C1 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 80216
