#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/72/2017276.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_2017276
loop_
_publ_author_name
'Sridhar, Balasubramanian'
'Ravikumar, Krishnan'
_publ_section_title
;
 Lamotrigine, an antiepileptic drug, and its chloride and nitrate salts
;
_journal_coeditor_code           DN3123
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o460
_journal_page_last               o464
_journal_paper_doi               10.1107/S0108270109030960
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H8 Cl2 N5 + , Cl -'
_chemical_formula_moiety         'C9 H8 Cl2 N5 + , Cl -'
_chemical_formula_sum            'C9 H8 Cl3 N5'
_chemical_formula_weight         292.55
_chemical_name_common            'Lamotriginium chloride'
_chemical_name_systematic
;
3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium chloride
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.588(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.664(5)
_cell_length_b                   5.5139(17)
_cell_length_c                   13.392(4)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.51
_cell_volume                     1200.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10623
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0466
_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)+(0.0615P)²+0.5312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                1645
_reflns_number_total             2119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3123.cif
_cod_data_source_block           II
_cod_original_cell_volume        1201.0(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017276
_cod_database_fobs_code          2017276
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.21676(18) 0.3960(6) 0.9622(2) 0.0346(7) Uani d . 1 . .
C C2 0.16292(18) 0.5422(6) 0.8953(2) 0.0347(7) Uani d . 1 . .
C C3 0.10250(19) 0.6702(6) 0.9294(2) 0.0418(8) Uani d . 1 . .
C C4 0.0939(2) 0.6449(7) 1.0288(3) 0.0498(9) Uani d . 1 . .
H H4 0.0534 0.7312 1.0516 0.060 Uiso calc R 1 . .
C C5 0.1454(2) 0.4920(7) 1.0944(3) 0.0498(9) Uani d . 1 . .
H H5 0.1381 0.4702 1.1607 0.060 Uiso calc R 1 . .
C C6 0.2077(2) 0.3706(6) 1.0624(2) 0.0427(8) Uani d . 1 . .
H H6 0.2436 0.2720 1.1078 0.051 Uiso calc R 1 . .
C C7 0.28538(18) 0.2693(6) 0.9280(2) 0.0337(7) Uani d . 1 . .
C C8 0.40791(18) 0.0504(6) 0.8620(2) 0.0358(7) Uani d . 1 . .
C C9 0.37029(18) 0.3494(5) 0.9584(2) 0.0332(7) Uani d . 1 . .
N N1 0.26640(15) 0.0880(5) 0.8662(2) 0.0388(6) Uani d . 1 . .
N N2 0.32909(16) -0.0200(5) 0.8340(2) 0.0404(7) Uani d . 1 . .
H H2N 0.315(2) -0.129(7) 0.789(3) 0.066(13) Uiso d . 1 . .
N N3 0.4632(2) -0.0745(6) 0.8269(2) 0.0492(8) Uani d . 1 . .
N N4 0.43016(14) 0.2373(5) 0.92572(18) 0.0353(6) Uani d . 1 . .
H H3N 0.446(2) -0.184(7) 0.784(3) 0.056(12) Uiso d . 1 . .
H H4N 0.516(2) -0.030(6) 0.841(2) 0.044(10) Uiso d . 1 . .
N N5 0.38916(19) 0.5389(5) 1.0188(2) 0.0452(7) Uani d . 1 . .
H H5N 0.440(2) 0.587(6) 1.034(2) 0.039(9) Uiso d . 1 . .
H H6N 0.351(2) 0.615(6) 1.042(3) 0.048(10) Uiso d . 1 . .
Cl Cl1 0.17094(5) 0.56486(16) 0.76934(6) 0.0467(3) Uani d . 1 . .
Cl Cl2 0.03727(7) 0.8640(2) 0.84802(8) 0.0719(4) Uani d . 1 . .
Cl Cl3 0.35241(5) -0.43520(15) 0.67219(6) 0.0443(3) Uani d . 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.6(3) ?
C2 C1 C7 . . 120.4(3) ?
C6 C1 C7 . . 120.0(3) ?
C1 C2 C3 . . 119.9(3) ?
C1 C2 Cl1 . . 119.9(2) ?
C3 C2 Cl1 . . 120.2(2) ?
C4 C3 C2 . . 120.2(3) ?
C4 C3 Cl2 . . 119.2(3) ?
C2 C3 Cl2 . . 120.5(3) ?
C5 C4 C3 . . 119.9(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.4(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N1 C7 C9 . . 120.1(3) ?
N1 C7 C1 . . 117.4(3) ?
C9 C7 C1 . . 122.4(3) ?
N3 C8 N4 . . 120.9(3) ?
N3 C8 N2 . . 117.8(3) ?
N4 C8 N2 . . 121.3(3) ?
N5 C9 N4 . . 118.5(3) ?
N5 C9 C7 . . 120.0(3) ?
N4 C9 C7 . . 121.5(3) ?
C7 N1 N2 . . 116.5(3) ?
C8 N2 N1 . . 124.1(3) ?
C8 N2 H2N . . 120(3) ?
N1 N2 H2N . . 115(3) ?
C8 N3 H3N . . 117(3) ?
C8 N3 H4N . . 121(2) ?
H3N N3 H4N . . 121(3) ?
C9 N4 C8 . . 116.5(3) ?
C9 N5 H5N . . 118(2) ?
C9 N5 H6N . . 121(2) ?
H5N N5 H6N . . 121(3) ?
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 . 1.381(4) ?
C1 C6 . 1.390(4) ?
C1 C7 . 1.494(4) ?
C2 C3 . 1.386(4) ?
C2 Cl1 . 1.725(3) ?
C3 C4 . 1.377(5) ?
C3 Cl2 . 1.731(3) ?
C4 C5 . 1.374(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.293(4) ?
C7 C9 . 1.453(4) ?
C8 N3 . 1.316(4) ?
C8 N4 . 1.337(4) ?
C8 N2 . 1.342(4) ?
C9 N5 . 1.317(4) ?
C9 N4 . 1.326(4) ?
N1 N2 . 1.352(4) ?
N2 H2N . 0.85(4) ?
N3 H3N . 0.84(4) ?
N3 H4N . 0.89(4) ?
N5 H5N . 0.88(3) ?
N5 H6N . 0.87(4) ?
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
N2 H2N Cl3 . 0.85(4) 2.47(4) 3.233(3) 150(3)
N3 H3N Cl3 . 0.84(4) 2.36(4) 3.160(4) 160(3)
N3 H4N Cl3 2_656 0.89(4) 2.30(4) 3.165(4) 164(3)
N5 H5N N4 3_667 0.88(3) 2.32(3) 3.189(4) 173(3)
N5 H6N Cl3 4_566 0.87(4) 2.48(4) 3.149(3) 135(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.6(5) ?
C7 C1 C2 C3 . . . . -176.2(3) ?
C6 C1 C2 Cl1 . . . . -177.3(2) ?
C7 C1 C2 Cl1 . . . . 3.9(4) ?
C1 C2 C3 C4 . . . . -2.5(5) ?
Cl1 C2 C3 C4 . . . . 177.4(3) ?
C1 C2 C3 Cl2 . . . . 177.3(2) ?
Cl1 C2 C3 Cl2 . . . . -2.8(4) ?
C2 C3 C4 C5 . . . . -0.1(5) ?
Cl2 C3 C4 C5 . . . . -179.9(3) ?
C3 C4 C5 C6 . . . . 2.6(6) ?
C4 C5 C6 C1 . . . . -2.4(6) ?
C2 C1 C6 C5 . . . . -0.2(5) ?
C7 C1 C6 C5 . . . . 178.6(3) ?
C2 C1 C7 N1 . . . . -72.4(4) ?
C6 C1 C7 N1 . . . . 108.8(3) ?
C2 C1 C7 C9 . . . . 104.9(3) ?
C6 C1 C7 C9 . . . . -73.9(4) ?
N1 C7 C9 N5 . . . . 177.8(3) ?
C1 C7 C9 N5 . . . . 0.6(5) ?
N1 C7 C9 N4 . . . . -1.5(4) ?
C1 C7 C9 N4 . . . . -178.7(3) ?
C9 C7 N1 N2 . . . . 0.9(4) ?
C1 C7 N1 N2 . . . . 178.2(3) ?
N3 C8 N2 N1 . . . . 178.4(3) ?
N4 C8 N2 N1 . . . . 0.1(5) ?
C7 N1 N2 C8 . . . . -0.2(5) ?
N5 C9 N4 C8 . . . . -178.0(3) ?
C7 C9 N4 C8 . . . . 1.3(4) ?
N3 C8 N4 C9 . . . . -178.9(3) ?
N2 C8 N4 C9 . . . . -0.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654185
