#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:16:50 +0200 (vie 13 de oct de 2017) $
#$Revision: 201980 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/00/2310006.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_2310006
loop_
_publ_author_name
'Dadda, Noureddine'
'Nassour, Ayoub'
'Guillot, Beno\?ît'
'Benali-Cherif, Nourredine'
'Jelsch, Christian'
_publ_contact_author             'Christian Jelsch'
_publ_section_title
;
 Charge-density analysis and electrostatic properties of
 2-carboxy-4-methylanilinium chloride monohydrate obtained using a
 multipolar and a spherical-charges model
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section A'
_journal_page_first              452
_journal_page_last               463
_journal_paper_doi               10.1107/S0108767312016571
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C8 H10 N O2, H2 O, Cl'
_chemical_formula_sum            'C8 H12 Cl N O3'
_chemical_formula_weight         205.631
_chemical_name_systematic
;
2-carboxy-4-methylanilinium chloride monohydride
;
_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           MoPro
_cell_angle_alpha                90.00
_cell_angle_beta                 96.772(24)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0511(45)
_cell_length_b                   4.9629(17)
_cell_length_c                   19.5625(154)
_cell_measurement_reflns_used    2630
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      4.08
_cell_volume                     969.0(9)
_computing_molecular_graphics    'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_publication_material  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Appex II CCD detector'
_diffrn_measurement_method       'w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.01793
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2368
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         28.13
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'R. H. Blessing(1995) Acta. Cryst. A51,33-38.'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0348
_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)+(0.1P)²+0.01P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2083
_reflns_number_total             2276
_reflns_threshold_expression     >2.0sigma(I)
_iucr_refine_instructions_details
; 
TITL 2-Carboxy-4-methylanilinium chloride monohydrate. IAM refinement
;
_cod_data_source_file            pc5010.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2310006
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_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Cl CL1 0.840005(4) 0.50212(7) 0.32288(2) 0.0152(1) Uani 1 d .
O O2 0.3736(1) 0.5245(2) 0.36543(8) 0.0208(3) Uani 1 d .
O O1 0.1742(1) 0.4690(2) 0.30180(7) 0.0177(3) Uani 1 d .
O O3 0.5710(1) 0.3271(2) 0.23972(6) 0.0193(3) Uani 1 d .
N N1 0.0343(2) 0.0124(2) 0.32497(8) 0.0145(4) Uani 1 d .
C C1 0.2279(2) 0.2010(3) 0.40341(8) 0.0141(4) Uani 1 d .
C C6 0.3078(2) 0.1902(3) 0.46724(8) 0.0161(4) Uani 1 d .
C C3 0.0972(2) -0.1695(3) 0.44081(9) 0.0157(4) Uani 1 d .
C C4 0.1776(2) -0.1740(3) 0.50391(9) 0.0169(4) Uani 1 d .
C C7 0.3713(2) 0.0019(3) 0.5870(1) 0.0213(5) Uani 1 d .
C C5 0.2845(2) 0.0050(3) 0.51811(10) 0.0155(5) Uani 1 d .
C C2 0.1218(2) 0.0166(3) 0.39086(9) 0.0135(4) Uani 1 d .
C C8 0.2539(2) 0.4093(3) 0.35127(8) 0.0143(4) Uani 1 d .
H H3 0.02700 -0.29142 0.43216 0.01881 Uiso 1 d R
H H6 0.37877 0.31050 0.47587 0.01933 Uiso 1 d R
H H4 0.15975 -0.29857 0.53717 0.02024 Uiso 1 d R
H H1A 0.08439 0.01226 0.29036 0.02179 Uiso 1 d R
H H1C -0.01802 0.15755 0.32198 0.02179 Uiso 1 d R
H H1B -0.01628 -0.13526 0.32274 0.02179 Uiso 1 d R
H H2 0.38308 0.64041 0.33651 0.03121 Uiso 1 d R
H H7A 0.32283 0.08056 0.62145 0.03199 Uiso 1 d R
H H7B 0.39458 -0.18059 0.59948 0.03199 Uiso 1 d R
H H7C 0.45144 0.10386 0.58362 0.03199 Uiso 1 d R
H H1W 0.52536 0.46435 0.23820 0.02895 Uiso 1 d R
H H2W 0.64006 0.37879 0.26246 0.02895 Uiso 1 d R
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
CL1 0.0145(3) 0.0148(3) 0.0161(3) -0.0012(1) 0.0012(2) -0.0006(1)
O2 0.0172(7) 0.0222(7) 0.0222(7) -0.0058(5) -0.0007(5) 0.0077(5)
O1 0.0190(7) 0.0173(6) 0.0162(7) -0.0014(4) -0.0010(5) 0.0022(4)
O3 0.0154(6) 0.0203(6) 0.0212(6) 0.0023(5) -0.0018(5) -0.0052(5)
N1 0.0164(8) 0.0146(8) 0.0121(7) -0.0006(5) -0.0002(6) -0.0005(5)
C1 0.0146(7) 0.0136(8) 0.0143(8) 0.0014(6) 0.0021(6) -0.0005(6)
C6 0.0149(7) 0.0164(8) 0.0168(8) -0.0001(6) 0.0008(6) -0.0014(6)
C3 0.0164(8) 0.0150(8) 0.0157(8) -0.0010(6) 0.0021(6) -0.0006(6)
C4 0.0192(8) 0.0168(8) 0.0148(8) 0.0010(6) 0.0032(6) 0.0011(6)
C7 0.0212(9) 0.0264(10) 0.0152(9) -0.0009(6) -0.0029(7) 0.0021(6)
C5 0.0148(8) 0.0181(10) 0.0133(9) 0.0027(5) 0.0002(7) -0.0013(5)
C2 0.0144(8) 0.0134(9) 0.0124(8) 0.0027(5) -0.0000(7) -0.0018(5)
C8 0.0159(7) 0.0122(8) 0.0151(8) -0.0011(6) 0.0035(6) -0.0015(6)
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
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Cl Cl 0.1484 0.1585
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C8 O1 123.7(2)
O2 C8 C1 112.4(2)
O1 C8 C1 123.9(2)
N1 C2 C1 121.7(2)
N1 C2 C3 118.0(1)
C1 C2 C3 120.3(2)
C1 C6 C5 122.2(2)
C1 C6 H6 118.9
C6 C5 C4 117.9(2)
C6 C5 C7 120.9(1)
C6 C1 C8 120.3(2)
C6 C1 C2 118.3(2)
C3 C4 C5 121.2(2)
C3 C4 H4 119.4
C4 C5 C7 121.3(2)
C4 C3 C2 120.1(2)
C4 C3 H3 119.9
C5 C6 H6 118.9
C5 C4 H4 119.4
C5 C7 H7A 109.5
C5 C7 H7B 109.5
C5 C7 H7C 109.5
C2 N1 H1C 109.5
C2 N1 H1B 109.5
C2 N1 H1A 109.5
C2 C1 C8 121.4(1)
C2 C3 H3 119.9
C8 O2 H2 109.5
H1A N1 H1C 109.5
H1A N1 H1B 109.5
H1C N1 H1B 109.5
H1W O3 H2W 101.2
H7B C7 H7A 109.5
H7B C7 H7C 109.5
H7C C7 H7A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.331(2)
O2 H2 0.820
O1 C8 1.218(2)
O3 H1W 0.820
O3 H2W 0.820
N1 C2 1.472(3)
N1 H1C 0.890
N1 H1B 0.890
N1 H1A 0.890
C1 C8 1.497(3)
C1 C2 1.405(3)
C1 C6 1.404(3)
C6 C5 1.395(3)
C6 H6 0.930
C3 C2 1.388(3)
C3 C4 1.393(3)
C3 H3 0.930
C4 C5 1.397(3)
C4 H4 0.930
C7 C5 1.516(3)
C7 H7A 0.960
C7 H7B 0.960
C7 H7C 0.960
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
O2 C8 C1 C2 -166.2(1)
O2 C8 C1 C6 15.4(1)
O1 C8 O2 H2 1.1
O1 C8 C1 C2 14.5(2)
O1 C8 C1 C6 -163.9(1)
N1 C2 C1 C8 2.3(1)
N1 C2 C1 C6 -179.2(1)
N1 C2 C3 C4 179.8(2)
N1 C2 C3 H3 -0.2
C1 C8 O2 H2 -178.2
C1 C2 N1 H1C -71.1
C1 C2 N1 H1B 168.9
C1 C2 N1 H1A 48.9
C1 C2 C3 C4 0.2(2)
C1 C2 C3 H3 -179.8
C1 C6 C5 C4 0.2(2)
C1 C6 C5 C7 -178.9(2)
C6 C5 C4 C3 0.4(2)
C6 C5 C4 H4 -179.6
C6 C5 C7 H7A 104.6
C6 C5 C7 H7B -135.4
C6 C5 C7 H7C -15.4
C6 C1 C2 C3 0.4(1)
C3 C2 N1 H1C 109.3
C3 C2 N1 H1B -10.7
C3 C2 N1 H1A -130.7
C3 C2 C1 C8 -178.1(2)
C3 C4 C5 C7 179.5(2)
C4 C5 C6 H6 -179.8
C4 C5 C7 H7A -74.4
C4 C5 C7 H7B 45.6
C4 C5 C7 H7C 165.6
C7 C5 C6 H6 1.1
C7 C5 C4 H4 -0.5
C5 C6 C1 C8 177.9(2)
C5 C6 C1 C2 -0.5(2)
C5 C4 C3 C2 -0.6(2)
C5 C4 C3 H3 179.4
C2 C1 C6 H6 179.5
C2 C3 C4 H4 179.4
C8 C1 C6 H6 -2.1
H3 C3 C4 H4 -0.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658416
