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#$Date: 2024-05-11 04:45:11 +0300 (Sat, 11 May 2024) $
#$Revision: 291812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312495.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_2312495
loop_
_publ_author_name
'Pavlović, Gordana'
'Lekšić, Edislav'
'Meštrović, Ernest'
_publ_section_title
;
 Supramolecular synthons in hydrates and solvates of lamotrigine: a tool
 for cocrystal design.
;
_journal_coeditor_code           AW5084
_journal_issue                   3
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_paper_doi               10.1107/S2052520624002567
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C9 H7 Cl2 N5, C2 H3 N'
_chemical_formula_sum            'C11 H10 Cl2 N6'
_chemical_formula_weight         297.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                69.598(6)
_cell_angle_beta                 82.227(5)
_cell_angle_gamma                82.015(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9855(4)
_cell_length_b                   8.6004(5)
_cell_length_c                   10.9109(7)
_cell_measurement_reflns_used    2878
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.2064
_cell_measurement_theta_min      4.3388
_cell_volume                     692.48(7)
_computing_cell_refinement
'CrysAlis RED, Oxford Diffraction Ltd.Version 1.171.36.21'
_computing_data_collection
'CrysAlis CCD, Oxford Diffraction Ltd.Version 1.171.36.21'
_computing_data_reduction
'CrysAlis RED, Oxford Diffraction Ltd.Version 1.171.36.21'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5383
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.342
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21.
Empirical absorption correction using 
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       'block prism'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1224P)²+0.2081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2430
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5084.cif
_cod_data_source_block           LAM_acetonitrile_solvate
_cod_database_code               2312495
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.46106(8) 0.33991(8) 0.73313(7) 0.0666(3) Uani 1 1 d . . . . .
Cl2 Cl 0.24043(8) 0.04639(10) 0.77877(7) 0.0711(3) Uani 1 1 d . . . . .
N1 N 0.8385(3) 0.2641(3) 0.92386(19) 0.0517(5) Uani 1 1 d . . . . .
N2 N 0.9300(3) 0.3850(3) 0.92135(19) 0.0530(5) Uani 1 1 d . . . . .
N3 N 1.0867(3) 0.6000(3) 0.8051(2) 0.0550(5) Uani 1 1 d D . . . .
N4 N 0.9872(2) 0.4587(2) 0.68806(17) 0.0439(4) Uani 1 1 d . . . . .
N5 N 0.8811(3) 0.3112(3) 0.5812(2) 0.0578(6) Uani 1 1 d D . . . .
N6 N 0.3554(6) 0.8047(7) 0.5603(5) 0.1205(14) Uani 1 1 d . . . . .
C1 C 0.7137(3) 0.1019(3) 0.8297(2) 0.0426(5) Uani 1 1 d . . . . .
C2 C 0.5468(3) 0.1355(3) 0.7964(2) 0.0454(5) Uani 1 1 d . . . . .
C3 C 0.4480(3) 0.0056(3) 0.8184(2) 0.0487(5) Uani 1 1 d . . . . .
C4 C 0.5145(3) -0.1578(3) 0.8738(2) 0.0540(6) Uani 1 1 d . . . . .
H4 H 0.4479 -0.2444 0.8891 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6790(3) -0.1919(3) 0.9062(3) 0.0544(6) Uani 1 1 d . . . . .
H5 H 0.7239 -0.3020 0.9427 0.065 Uiso 1 1 calc R U . . .
C6 C 0.7794(3) -0.0632(3) 0.8849(2) 0.0490(5) Uani 1 1 d . . . . .
H6 H 0.8906 -0.0876 0.9075 0.059 Uiso 1 1 calc R U . . .
C7 C 0.8183(3) 0.2396(3) 0.8155(2) 0.0426(5) Uani 1 1 d . . . . .
C8 C 0.9993(3) 0.4774(3) 0.8040(2) 0.0430(5) Uani 1 1 d . . . . .
C9 C 0.8963(3) 0.3381(3) 0.6926(2) 0.0423(5) Uani 1 1 d . . . . .
C10 C 0.4992(7) 0.7841(5) 0.5660(4) 0.0895(11) Uani 1 1 d . . . . .
C11 C 0.6768(6) 0.7575(6) 0.5731(4) 0.1052(14) Uani 1 1 d . . . . .
H11A H 0.7014 0.6782 0.6572 0.158 Uiso 1 1 calc R U . . .
H11B H 0.7198 0.8610 0.5617 0.158 Uiso 1 1 calc R U . . .
H11C H 0.7297 0.7153 0.5050 0.158 Uiso 1 1 calc R U . . .
H2N3 H 1.093(7) 0.625(7) 0.874(3) 0.126 Uiso 1 1 d D U . . .
H2N5 H 0.927(7) 0.375(5) 0.509(3) 0.126 Uiso 1 1 d D U . . .
H1N3 H 1.135(6) 0.664(5) 0.734(3) 0.126 Uiso 1 1 d D U . . .
H1N5 H 0.823(6) 0.236(5) 0.579(6) 0.126 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 120.63(19) . . ?
C8 N2 N1 117.33(19) . . ?
C8 N3 H2N3 124(4) . . ?
C8 N3 H1N3 121(4) . . ?
H2N3 N3 H1N3 115(5) . . ?
C9 N4 C8 115.90(18) . . ?
C9 N5 H2N5 118(3) . . ?
C9 N5 H1N5 123(4) . . ?
H2N5 N5 H1N5 119(5) . . ?
C6 C1 C2 118.9(2) . . ?
C6 C1 C7 119.8(2) . . ?
C2 C1 C7 121.2(2) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 Cl1 120.20(18) . . ?
C1 C2 Cl1 119.48(17) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 Cl2 119.26(19) . . ?
C2 C3 Cl2 120.53(19) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C9 120.6(2) . . ?
N1 C7 C1 116.15(19) . . ?
C9 C7 C1 123.20(19) . . ?
N2 C8 N3 115.6(2) . . ?
N2 C8 N4 125.9(2) . . ?
N3 C8 N4 118.6(2) . . ?
N4 C9 N5 119.00(19) . . ?
N4 C9 C7 119.61(19) . . ?
N5 C9 C7 121.4(2) . . ?
N6 C10 C11 179.6(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.727(2) . ?
Cl2 C3 1.727(3) . ?
N1 C7 1.305(3) . ?
N1 N2 1.342(3) . ?
N2 C8 1.341(3) . ?
N3 C8 1.346(3) . ?
N3 H2N3 0.863(10) . ?
N3 H1N3 0.858(10) . ?
N4 C9 1.330(3) . ?
N4 C8 1.347(3) . ?
N5 C9 1.338(3) . ?
N5 H2N5 0.857(10) . ?
N5 H1N5 0.858(10) . ?
N6 C10 1.145(6) . ?
C1 C6 1.392(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.495(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.381(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.426(3) . ?
C10 C11 1.412(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 -0.3(4) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C7 C1 C2 C3 -175.77(19) . . . . ?
C6 C1 C2 Cl1 177.79(16) . . . . ?
C7 C1 C2 Cl1 1.9(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
Cl1 C2 C3 C4 -177.46(18) . . . . ?
C1 C2 C3 Cl2 179.41(16) . . . . ?
Cl1 C2 C3 Cl2 1.7(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
Cl2 C3 C4 C5 -179.77(19) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 175.9(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
N2 N1 C7 C9 1.5(4) . . . . ?
N2 N1 C7 C1 -179.9(2) . . . . ?
C6 C1 C7 N1 -72.2(3) . . . . ?
C2 C1 C7 N1 103.7(3) . . . . ?
C6 C1 C7 C9 106.4(3) . . . . ?
C2 C1 C7 C9 -77.8(3) . . . . ?
N1 N2 C8 N3 178.4(2) . . . . ?
N1 N2 C8 N4 -0.9(4) . . . . ?
C9 N4 C8 N2 0.7(4) . . . . ?
C9 N4 C8 N3 -178.6(2) . . . . ?
C8 N4 C9 N5 -179.1(2) . . . . ?
C8 N4 C9 C7 0.5(3) . . . . ?
N1 C7 C9 N4 -1.7(3) . . . . ?
C1 C7 C9 N4 179.8(2) . . . . ?
N1 C7 C9 N5 178.0(2) . . . . ?
C1 C7 C9 N5 -0.5(4) . . . . ?
