#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/33/2003362.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_2003362
loop_
_publ_author_name
'Janes, R. W.'
'Palmer, R. A.'
_publ_section_title
;
 3,5-Diamino-6-(2-methylphenyl)-1,2,4-triazine Monohydrate: an Analogue
 of Lamotrigine
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              685
_journal_page_last               688
_journal_paper_doi               10.1107/S0108270194009352
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'Crystallized from acetonitrile'
_chemical_formula_moiety         '2(C10 H11 N5),H2 O1'
_chemical_formula_sum            'C10 H12 N5 O0.5'
_chemical_formula_weight         210.2
_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_type_scat_source           'SHELX76 (Sheldrick, 1976)'
_cell_angle_alpha                90
_cell_angle_beta                 95.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.672(2)
_cell_length_b                   11.690(2)
_cell_length_c                   19.184(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      32
_cell_measurement_theta_min      9
_cell_volume                     2160.4(7)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0081
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8893
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        <10
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.73
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.29
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.37
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     341
_refine_ls_number_reflns         3373
_refine_ls_R_factor_obs          0.0566
_refine_ls_shift/esd_max         0.640
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1.0/[σ²(F) + 0.010180(F)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0767
_reflns_number_observed          3373
_reflns_number_total             4107
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            li1108.cif
_cod_data_source_block           li1108a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1.0/[\s^2^(F) +
0.010180(F)^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1.0/[\s^2^(F) + 0.010180(F)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2160.4(6)
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C20 H24 N10 O1'
_cod_database_code               2003362
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C1 -.1122(2) .4359(2) -.1331(1) .047(1)
C2 -.0946(2) .4560(2) -.2028(1) .054(1)
C3 -.1416(3) .5607(2) -.2326(1) .065(1)
C4 -.2049(3) .6407(2) -.1938(2) .071(1)
C5 -.2282(3) .6184(3) -.1253(2) .070(1)
C6 -.1809(3) .5167(2) -.0947(1) .060(1)
C21 -.0219(4) .3721(3) -.2456(2) .082(2)
N1 .0897(2) .3437(2) -.0792(1) .055(1)
N2 .1615(2) .2597(2) -.0450(1) .057(1)
C3t .0912(2) .1658(2) -.0280(1) .046(1)
N4 -.0451(2) .1482(1) -.0445(1) .046(1)
C5t -.1142(2) .2323(2) -.0798(1) .043(1)
C6t -.0440(2) .3352(2) -.0966(1) .047(1)
N3 .1651(2) .0867(2) .0091(1) .058(1)
N5 -.2488(2) .2193(2) -.0999(1) .056(1)
C1' .8190(2) .1842(2) .1726(1) .045(1)
C2' .8365(2) .2283(2) .2412(1) .051(1)
C3' .9337(3) .1752(2) .2887(1) .065(1)
C4' 1.0133(3) .0828(3) .2690(2) .072(1)
C5' .9967(3) .0427(2) .2025(2) .072(2)
C6' .8984(3) .0913(2) .1546(1) .058(1)
C21' .7545(3) .3271(3) .2653(2) .073(1)
N1' .6164(2) .1665(1) .0913(1) .044(1)
N2' .5211(2) .2060(1) .0409(1) .045(1)
C3t' .5309(2) .3161(2) .0224(1) .041(1)
N4' .6306(2) .3899(1) .0469(1) .045(1)
C5t' .7267(2) .3474(2) .0935(1) .047(1)
C6t' .7157(2) .2320(2) .1184(1) .043(1)
N3' .4354(2) .3548(2) -.0271(1) .050(1)
N5' .8346(2) .4129(2) .1151(1) .070(1)
O1A -.4651(2) .0562(2) -.0804(1) .077(1)
H3 -.1278(3) .5781(2) -.2869(1) ?
H4 -.2368(3) .7216(2) -.2172(2) ?
H5 -.2825(3) .6798(3) -.0957(2) ?
H6 -.1971(3) .4996(2) -.0407(1) ?
H21 -.0063(4) .2929(3) -.2170(2) ?
H22 .0743(4) .3979(3) -.2655(2) ?
H23 -.1002(4) .3600(3) -.2887(2) ?
H31 .2551(30) .1018(25) .0183(4) ?
H32 .1200(4) .0163(33) .0236(18) ?
H51 -.2976(32) .1610(27) -.0918(15) ?
H52 -.2898(31) .2724(27) -.1249(15) ?
H3' .9480(3) .2062(2) .3419(1) ?
H4' 1.0882(3) .0434(3) .3067(2) ?
H5' 1.0598(3) -.0275(2) .1870(2) ?
H6' .8833(3) .0565(2) .1023(1) ?
H21' .6629(3) .3502(3) .2319(2) ?
H22' .8312(3) .3939(3) .2639(2) ?
H23' .7274(3) .3162(3) .3183(2) ?
H31' .3582(36) .2977(30) -.0318(16) ?
H32' .4282(28) .4329(26) -.0408(14) ?
H51' .8496(32) .4815(30) .0984(15) ?
H52' .9059(31) .3857(26) .1404(16) ?
H1A -.5028(34) .0910(30) -.0434(18) ?
H2A -.5258(55) .0055(43) -.0940(25) ?
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
C1 C2 C3 118.5(2) yes
C2 C3 C4 121.0(2) yes
C3 C4 C5 120.5(3) yes
C4 C5 C6 119.4(3) yes
C5 C6 C1 120.6(2) yes
C6 C1 C2 119.9(2) yes
C2 C1 C6t 119.9(2) yes
C6 C1 C6t 119.8(2) yes
C1 C6t N1 116.3(2) yes
C6t N1 N2 121.7(2) yes
N1 N2 C3t 117.7(2) yes
N2 C3t N4 125.0(2) yes
C3t N4 C5t 116.3(2) yes
N4 C5t C6t 120.3(2) yes
C5t C6t N1 118.9(2) yes
C5t C6t C1 124.7(2) yes
N2 C3t N3 115.8(2) yes
N4 C3t N3 119.2(2) yes
N4 C5t N5 119.6(2) yes
C6t C5t N5 120.1(2) yes
C1 C2 C21 121.6(2) yes
C3 C2 C21 119.9(2) yes
C1' C2' C3' 117.7(2) yes
C2' C3' C4' 121.5(2) yes
C3' C4' C5' 120.1(2) yes
C4' C5' C6' 120.0(3) yes
C5' C6' C1' 121.2(2) yes
C6' C1' C2' 119.6(2) yes
C2' C1' C6t' 122.2(2) yes
C6' C1' C6t' 118.2(2) yes
C1' C6t' N1' 119.1(2) yes
C6t' N1' N2' 121.1(2) yes
N1' N2' C3t' 117.2(2) yes
N2' C3t' N4' 125.9(2) yes
C3t' N4' C5t' 115.6(2) yes
N4' C5t' C6t' 120.4(2) yes
C5t' C6t' N1' 119.5(2) yes
C5t' C6t' C1' 121.4(2) yes
N2' C3t' N3' 116.8(2) yes
N4' C3t' N3' 117.2(2) yes
N4' C5t' N5' 118.6(2) yes
C6t' C5t' N5' 121.0(2) yes
C1' C2' C21' 123.2(2) yes
C3' C2' C21' 119.1(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.384(3) yes
C3 C4 1.373(4) yes
C5 C6 1.386(4) yes
C1 C6t 1.493(3) yes
N1 N2 1.341(2) yes
C3t N4 1.344(3) yes
C5t C6t 1.432(2) yes
C5t N5 1.333(3) yes
C1' C2' 1.411(3) yes
C3' C4' 1.398(4) yes
C5' C6' 1.384(3) yes
C1' C6t' 1.485(2) yes
N1' N2' 1.355(2) yes
C3t' N4' 1.347(2) yes
C5t' C6t' 1.439(3) yes
C5t' N5' 1.331(2) yes
C2 C3 1.408(3) yes
C4 C5 1.378(4) yes
C6 C1 1.401(3) yes
C6t N1 1.310(3) yes
N2 C3t 1.346(3) yes
N4 C5t 1.338(3) yes
C3t N3 1.334(3) yes
C2 C21 1.494(4) yes
C2' C3' 1.395(3) yes
C4' C5' 1.355(4) yes
C6' C1' 1.391(3) yes
C6t' N1' 1.300(2) yes
N2' C3t' 1.341(2) yes
N4' C5t' 1.327(2) yes
C3t' N3' 1.342(2) yes
C2' C21' 1.497(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139054229
