#------------------------------------------------------------------------------
#$Date: 2024-05-11 03:45:11 +0200 (Sat 11 de May de 2024) $
#$Revision: 291812 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/24/2312493.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_2312493
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, C5 H12 O, H2 O'
_chemical_formula_sum            'C14 H21 Cl2 N5 O2'
_chemical_formula_weight         362.26
_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                84.043(8)
_cell_angle_beta                 75.989(8)
_cell_angle_gamma                85.943(9)
_cell_formula_units_Z            2
_cell_length_a                   7.6284(8)
_cell_length_b                   8.5181(9)
_cell_length_c                   14.5190(13)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.7683
_cell_measurement_theta_min      3.1476
_cell_volume                     909.41(16)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.957
_diffrn_reflns_theta_min         3.150
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30472
_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    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0624
_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)+(0.1160P)²+0.1605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2735
_reflns_number_total             3448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5084.cif
_cod_data_source_block           LAM_n-pentanol_solvate
_cod_database_code               2312493
_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 0.27370(10) 0.13131(15) 0.14817(7) 0.1069(4) Uani 1 1 d . . . . .
Cl2 Cl 0.01605(15) 0.23352(17) 0.01237(6) 0.1211(5) Uani 1 1 d . . . . .
O1 O 0.2661(3) 0.4404(2) 0.48819(16) 0.0716(5) Uani 1 1 d D . . . .
H1O H 0.191(4) 0.449(5) 0.5388(17) 0.107 Uiso 1 1 d D U . . .
H2O H 0.251(6) 0.530(2) 0.463(3) 0.107 Uiso 1 1 d D U . . .
O2 O 0.9522(3) 0.5374(3) 0.32149(18) 0.0841(6) Uani 1 1 d D . . . .
H1O2 H 0.997(6) 0.612(4) 0.336(3) 0.126 Uiso 1 1 d D U . . .
N1 N 0.1284(3) -0.1878(2) 0.35341(15) 0.0581(5) Uani 1 1 d . . . . .
N2 N 0.2387(3) -0.2494(2) 0.40928(15) 0.0597(5) Uani 1 1 d . . . . .
N3 N 0.4362(3) -0.2087(2) 0.49918(18) 0.0682(6) Uani 1 1 d D . . . .
H1N3 H 0.485(4) -0.3039(18) 0.501(2) 0.082 Uiso 1 1 d D U . . .
H2N3 H 0.510(4) -0.151(4) 0.518(2) 0.082 Uiso 1 1 d D U . . .
N4 N 0.2907(3) 0.0107(2) 0.44159(14) 0.0529(5) Uani 1 1 d . . . . .
N5 N 0.1348(4) 0.2235(2) 0.38520(19) 0.0702(6) Uani 1 1 d D . . . .
H1N5 H 0.064(4) 0.267(4) 0.351(2) 0.084 Uiso 1 1 d D U . . .
H2N5 H 0.190(4) 0.285(3) 0.412(2) 0.084 Uiso 1 1 d D U . . .
C1 C -0.0216(3) 0.0203(3) 0.27542(17) 0.0541(5) Uani 1 1 d . . . . .
C2 C 0.0460(3) 0.0957(3) 0.18461(19) 0.0636(6) Uani 1 1 d . . . . .
C3 C -0.0665(4) 0.1397(4) 0.1240(2) 0.0727(7) Uani 1 1 d . . . . .
C4 C -0.2471(4) 0.1087(5) 0.1523(2) 0.0843(9) Uani 1 1 d . . . . .
H4 H -0.3231 0.1383 0.1115 0.101 Uiso 1 1 calc R U . . .
C5 C -0.3146(4) 0.0344(5) 0.2406(2) 0.0877(10) Uani 1 1 d . . . . .
H5 H -0.4365 0.0127 0.2593 0.105 Uiso 1 1 calc R U . . .
C6 C -0.2042(4) -0.0085(4) 0.3018(2) 0.0713(7) Uani 1 1 d . . . . .
H6 H -0.2528 -0.0577 0.3620 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0987(3) -0.0359(3) 0.34013(17) 0.0521(5) Uani 1 1 d . . . . .
C8 C 0.3188(3) -0.1473(3) 0.44805(17) 0.0526(5) Uani 1 1 d . . . . .
C9 C 0.1762(3) 0.0687(3) 0.38919(17) 0.0522(5) Uani 1 1 d . . . . .
C10 C 0.8711(6) 0.5668(5) 0.2422(3) 0.1071(12) Uani 1 1 d D U . . .
H10A H 0.9444 0.5141 0.1888 0.128 Uiso 1 1 calc R U . . .
H10B H 0.8678 0.6793 0.2232 0.128 Uiso 1 1 calc R U . . .
C11 C 0.6899(7) 0.5117(8) 0.2642(4) 0.1371(19) Uani 1 1 d D U . . .
H11A H 0.6162 0.5682 0.3158 0.165 Uiso 1 1 calc R U . . .
H11B H 0.6934 0.4005 0.2867 0.165 Uiso 1 1 calc R U . . .
C12 C 0.6011(9) 0.5326(9) 0.1811(4) 0.175(3) Uani 1 1 d D U . . .
H12A H 0.6951 0.5177 0.1239 0.209 Uiso 0.61 1 calc R U P A 1
H12B H 0.5198 0.4471 0.1891 0.209 Uiso 0.61 1 calc R U P A 1
H12C H 0.6516 0.6255 0.1420 0.209 Uiso 0.39 1 calc R U P B 2
H12D H 0.6450 0.4434 0.1441 0.209 Uiso 0.39 1 calc R U P B 2
C13A C 0.5030(12) 0.6739(11) 0.1637(6) 0.136(3) Uani 0.61 1 d D U P C 1
H13A H 0.5860 0.7545 0.1317 0.163 Uiso 0.61 1 calc R U P C 1
H13B H 0.4349 0.7105 0.2237 0.163 Uiso 0.61 1 calc R U P C 1
C13B C 0.4112(13) 0.548(2) 0.1885(8) 0.140(5) Uani 0.39 1 d D U P C 2
H13C H 0.3523 0.5988 0.2455 0.168 Uiso 0.39 1 calc R U P C 2
H13D H 0.3634 0.4442 0.1937 0.168 Uiso 0.39 1 calc R U P C 2
C14 C 0.3704(10) 0.6473(11) 0.1002(5) 0.194(3) Uani 1 1 d D U . . .
H14A H 0.3043 0.7447 0.0888 0.291 Uiso 0.61 1 calc R U P C 1
H14B H 0.4382 0.6125 0.0405 0.291 Uiso 0.61 1 calc R U P C 1
H14C H 0.2873 0.5686 0.1324 0.291 Uiso 0.61 1 calc R U P C 1
H14D H 0.2420 0.6567 0.1063 0.291 Uiso 0.39 1 calc R U P C 2
H14E H 0.4163 0.7506 0.0957 0.291 Uiso 0.39 1 calc R U P C 2
H14F H 0.4274 0.5964 0.0439 0.291 Uiso 0.39 1 calc R U P C 2
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'
O O 0.0492 0.0322 '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
H1O O1 H2O 97(4) . . ?
C10 O2 H1O2 116(3) . . ?
C7 N1 N2 121.04(19) . . ?
C8 N2 N1 117.05(18) . . ?
C8 N3 H1N3 128(2) . . ?
C8 N3 H2N3 123(2) . . ?
H1N3 N3 H2N3 105(3) . . ?
C9 N4 C8 115.91(19) . . ?
C9 N5 H1N5 122(2) . . ?
C9 N5 H2N5 120(2) . . ?
H1N5 N5 H2N5 118(3) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 120.4(2) . . ?
C2 C1 C7 121.7(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 Cl1 120.0(2) . . ?
C1 C2 Cl1 119.26(19) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 Cl2 119.1(2) . . ?
C2 C3 Cl2 120.9(2) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C9 120.0(2) . . ?
N1 C7 C1 116.9(2) . . ?
C9 C7 C1 123.13(19) . . ?
N2 C8 N3 116.85(19) . . ?
N2 C8 N4 126.0(2) . . ?
N3 C8 N4 117.1(2) . . ?
N4 C9 N5 118.4(2) . . ?
N4 C9 C7 119.71(19) . . ?
N5 C9 C7 121.9(2) . . ?
O2 C10 C11 111.9(4) . . ?
O2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
O2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 114.1(5) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13A C12 C11 120.1(6) . . ?
C13B C12 C11 125.3(7) . . ?
C13A C12 H12A 107.3 . . ?
C11 C12 H12A 107.3 . . ?
C13A C12 H12B 107.3 . . ?
C11 C12 H12B 107.3 . . ?
H12A C12 H12B 106.9 . . ?
C13B C12 H12C 106.0 . . ?
C11 C12 H12C 106.0 . . ?
C13B C12 H12D 106.0 . . ?
C11 C12 H12D 106.0 . . ?
H12C C12 H12D 106.3 . . ?
C12 C13A C14 110.3(6) . . ?
C12 C13A H13A 109.6 . . ?
C14 C13A H13A 109.6 . . ?
C12 C13A H13B 109.6 . . ?
C14 C13A H13B 109.6 . . ?
H13A C13A H13B 108.1 . . ?
C12 C13B C14 110.5(7) . . ?
C12 C13B H13C 109.5 . . ?
C14 C13B H13C 109.5 . . ?
C12 C13B H13D 109.5 . . ?
C14 C13B H13D 109.5 . . ?
H13C C13B H13D 108.1 . . ?
C13A C14 H14A 109.5 . . ?
C13A C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13A C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13B C14 H14D 109.5 . . ?
C13B C14 H14E 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C13B C14 H14F 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 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 1.728(3) . ?
Cl2 C3 1.723(3) . ?
O1 H1O 0.823(10) . ?
O1 H2O 0.823(10) . ?
O2 C10 1.427(4) . ?
O2 H1O2 0.813(10) . ?
N1 C7 1.300(3) . ?
N1 N2 1.349(3) . ?
N2 C8 1.338(3) . ?
N3 C8 1.342(3) . ?
N3 H1N3 0.869(10) . ?
N3 H2N3 0.875(10) . ?
N4 C9 1.329(3) . ?
N4 C8 1.345(3) . ?
N5 C9 1.333(3) . ?
N5 H1N5 0.864(10) . ?
N5 H2N5 0.870(10) . ?
C1 C6 1.385(4) . ?
C1 C2 1.400(4) . ?
C1 C7 1.489(3) . ?
C2 C3 1.380(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.435(3) . ?
C10 C11 1.441(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13A 1.405(8) . ?
C12 C13B 1.424(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C13A C14 1.565(7) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C13B C14 1.544(9) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 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 -1.6(4) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C1 C2 C3 176.7(2) . . . . ?
C6 C1 C2 Cl1 -179.1(2) . . . . ?
C7 C1 C2 Cl1 -2.5(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
Cl1 C2 C3 C4 178.8(3) . . . . ?
C1 C2 C3 Cl2 179.6(2) . . . . ?
Cl1 C2 C3 Cl2 -1.2(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
Cl2 C3 C4 C5 180.0(3) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C7 C1 C6 C5 -176.1(3) . . . . ?
N2 N1 C7 C9 -3.3(4) . . . . ?
N2 N1 C7 C1 178.6(2) . . . . ?
C6 C1 C7 N1 68.3(3) . . . . ?
C2 C1 C7 N1 -108.2(3) . . . . ?
C6 C1 C7 C9 -109.7(3) . . . . ?
C2 C1 C7 C9 73.8(3) . . . . ?
N1 N2 C8 N3 -176.4(2) . . . . ?
N1 N2 C8 N4 4.6(4) . . . . ?
C9 N4 C8 N2 -2.1(4) . . . . ?
C9 N4 C8 N3 178.9(2) . . . . ?
C8 N4 C9 N5 175.9(2) . . . . ?
C8 N4 C9 C7 -3.0(3) . . . . ?
N1 C7 C9 N4 5.8(4) . . . . ?
C1 C7 C9 N4 -176.2(2) . . . . ?
N1 C7 C9 N5 -173.1(3) . . . . ?
C1 C7 C9 N5 4.9(4) . . . . ?
O2 C10 C11 C12 -177.1(5) . . . . ?
C10 C11 C12 C13A -88.6(9) . . . . ?
C10 C11 C12 C13B -154.1(10) . . . . ?
C11 C12 C13A C14 -159.9(6) . . . . ?
C11 C12 C13B C14 151.2(9) . . . . ?
