#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/72/2017275.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_2017275
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 H7 Cl2 N5'
_chemical_formula_moiety         'C9 H7 Cl2 N5'
_chemical_formula_sum            'C9 H7 Cl2 N5'
_chemical_formula_weight         256.10
_chemical_name_common            Lamotrigine
_chemical_name_systematic
;
6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.172(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.136(3)
_cell_length_b                   8.6409(12)
_cell_length_c                   13.5549(18)
_cell_measurement_reflns_used    8111
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.29
_cell_volume                     2117.0(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9654
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0489P)²+1.6016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                1785
_reflns_number_total             1869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3123.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017275
_cod_database_fobs_code          2017275
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.90356(9) 0.18792(19) 0.02977(11) 0.0323(3) Uani d . 1 . .
C C2 0.97759(9) 0.19888(18) 0.09308(11) 0.0322(3) Uani d . 1 . .
C C3 1.01725(9) 0.06717(19) 0.13631(12) 0.0343(4) Uani d . 1 . .
C C4 0.98390(10) -0.07678(19) 0.11757(13) 0.0395(4) Uani d . 1 . .
H H4 1.0106 -0.1649 0.1468 0.047 Uiso calc R 1 . .
C C5 0.91100(11) -0.0891(2) 0.05540(14) 0.0435(4) Uani d . 1 . .
H H5 0.8885 -0.1858 0.0428 0.052 Uiso calc R 1 . .
C C6 0.87094(10) 0.0419(2) 0.01153(13) 0.0387(4) Uani d . 1 . .
H H6 0.8218 0.0322 -0.0305 0.046 Uiso calc R 1 . .
C C7 0.85971(8) 0.32755(19) -0.01719(11) 0.0321(3) Uani d . 1 . .
C C8 0.78227(9) 0.57302(18) -0.10430(12) 0.0320(3) Uani d . 1 . .
C C9 0.83559(8) 0.43671(18) 0.04445(12) 0.0321(3) Uani d . 1 . .
N N1 0.83969(8) 0.34528(17) -0.11885(10) 0.0379(3) Uani d . 1 . .
N N2 0.79947(8) 0.46909(17) -0.16605(10) 0.0389(3) Uani d . 1 . .
N N3 0.74525(9) 0.69972(19) -0.14875(13) 0.0435(4) Uani d . 1 . .
H H3N 0.7302(12) 0.710(3) -0.211(2) 0.054(6) Uiso d . 1 . .
H H4N 0.7319(11) 0.764(3) -0.1111(17) 0.048(6) Uiso d . 1 . .
N N4 0.79845(7) 0.56192(15) 0.00028(10) 0.0323(3) Uani d . 1 . .
N N5 0.84784(10) 0.4120(2) 0.14622(12) 0.0493(4) Uani d . 1 . .
H H5N 0.8311(11) 0.472(3) 0.1809(16) 0.047(6) Uiso d . 1 . .
H H6N 0.8731(13) 0.334(3) 0.1748(17) 0.056(6) Uiso d . 1 . .
Cl Cl1 1.02059(2) 0.37772(5) 0.11260(3) 0.04626(16) Uani d . 1 . .
Cl Cl2 1.10963(2) 0.07839(5) 0.21190(3) 0.04507(16) 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
C6 C1 C2 . . 118.36(15) ?
C6 C1 C7 . . 120.10(14) ?
C2 C1 C7 . . 121.54(14) ?
C3 C2 C1 . . 120.50(14) ?
C3 C2 Cl1 . . 120.12(12) ?
C1 C2 Cl1 . . 119.32(12) ?
C4 C3 C2 . . 120.33(15) ?
C4 C3 Cl2 . . 118.63(13) ?
C2 C3 Cl2 . . 121.01(13) ?
C5 C4 C3 . . 119.72(16) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.37(16) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 120.71(16) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
N1 C7 C9 . . 119.77(14) ?
N1 C7 C1 . . 118.22(13) ?
C9 C7 C1 . . 121.91(13) ?
N3 C8 N2 . . 118.05(15) ?
N3 C8 N4 . . 115.87(15) ?
N2 C8 N4 . . 126.08(15) ?
N4 C9 N5 . . 118.85(15) ?
N4 C9 C7 . . 120.12(14) ?
N5 C9 C7 . . 120.99(15) ?
C7 N1 N2 . . 120.96(13) ?
C8 N2 N1 . . 116.98(13) ?
C8 N3 H3N . . 121.4(16) ?
C8 N3 H4N . . 119.1(14) ?
H3N N3 H4N . . 119(2) ?
C9 N4 C8 . . 115.86(13) ?
C9 N5 H5N . . 121.1(15) ?
C9 N5 H6N . . 118.7(15) ?
H5N N5 H6N . . 120(2) ?
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 C6 . 1.393(2) ?
C1 C2 . 1.398(2) ?
C1 C7 . 1.488(2) ?
C2 C3 . 1.387(2) ?
C2 Cl1 . 1.7298(16) ?
C3 C4 . 1.383(2) ?
C3 Cl2 . 1.7305(17) ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.312(2) ?
C7 C9 . 1.433(2) ?
C8 N3 . 1.335(2) ?
C8 N2 . 1.340(2) ?
C8 N4 . 1.351(2) ?
C9 N4 . 1.325(2) ?
C9 N5 . 1.338(2) ?
N1 N2 . 1.350(2) ?
N3 H3N . 0.80(2) ?
N3 H4N . 0.85(2) ?
N5 H5N . 0.83(2) ?
N5 H6N . 0.85(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
N3 H3N N1 4_654 0.80(2) 2.54(2) 3.284(2) 155(2)
N3 H4N N4 7_665 0.85(2) 2.33(2) 3.178(2) 176.7(19)
N5 H5N N2 6_566 0.83(2) 2.40(2) 3.152(2) 151.3(19)
N5 H6N Cl2 2_755 0.85(3) 2.65(2) 3.4121(18) 151(2)
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 . . . . 0.1(2) ?
C7 C1 C2 C3 . . . . 179.75(13) ?
C6 C1 C2 Cl1 . . . . 177.32(11) ?
C7 C1 C2 Cl1 . . . . -2.99(19) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
Cl1 C2 C3 C4 . . . . -177.48(12) ?
C1 C2 C3 Cl2 . . . . 178.22(11) ?
Cl1 C2 C3 Cl2 . . . . 0.98(18) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
Cl2 C3 C4 C5 . . . . -178.30(12) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 C1 . . . . -0.2(3) ?
C2 C1 C6 C5 . . . . 0.2(2) ?
C7 C1 C6 C5 . . . . -179.53(15) ?
C6 C1 C7 N1 . . . . -68.7(2) ?
C2 C1 C7 N1 . . . . 111.63(17) ?
C6 C1 C7 C9 . . . . 107.69(18) ?
C2 C1 C7 C9 . . . . -72.0(2) ?
N1 C7 C9 N4 . . . . -5.6(2) ?
C1 C7 C9 N4 . . . . 178.08(14) ?
N1 C7 C9 N5 . . . . 172.17(17) ?
C1 C7 C9 N5 . . . . -4.2(2) ?
C9 C7 N1 N2 . . . . 3.1(2) ?
C1 C7 N1 N2 . . . . 179.60(14) ?
N3 C8 N2 N1 . . . . 177.19(15) ?
N4 C8 N2 N1 . . . . -3.3(2) ?
C7 N1 N2 C8 . . . . 1.0(2) ?
N5 C9 N4 C8 . . . . -174.33(15) ?
C7 C9 N4 C8 . . . . 3.5(2) ?
N3 C8 N4 C9 . . . . -179.57(14) ?
N2 C8 N4 C9 . . . . 0.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3741
