#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:27:28 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246186 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311959.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_2311959
loop_
_publ_author_name
'Sridhar, Balasubramanian'
'Ravikumar, Krishnan'
_publ_section_title
;
 Role of halogen-halogen contacts in the crystal structures of three new
 solvates of the drug oxyclozanide.
;
_journal_coeditor_code           EG3229
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              1056
_journal_page_last               1063
_journal_paper_doi               10.1107/S2053229617015923
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C13 H6 Cl5 N O3, C8 H10'
_chemical_formula_moiety         'C13 H6 Cl5 N O3, 0.5(C8 H10)'
_chemical_formula_sum            'C17 H11 Cl5 N O3'
_chemical_formula_weight         454.52
_chemical_name_common
;
Oxyclozanide xylene hemisolvate
;
_chemical_name_systematic
;
2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide
xylene hemisolvate
;
_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                83.7014(5)
_cell_angle_beta                 80.0916(5)
_cell_angle_gamma                67.8388(4)
_cell_formula_units_Z            2
_cell_length_a                   7.12429(8)
_cell_length_b                   9.40484(11)
_cell_length_c                   14.27988(16)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.69
_cell_volume                     871.840(17)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33198
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_min         2.341
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker,2016
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0255P)²+0.9635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                3962
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eg3229sup1.cif
_cod_data_source_block           II
_cod_database_code               2311959
_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.
;
_shelx_estimated_absorpt_t_min   0.716
_shelx_estimated_absorpt_t_max   0.822
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
C C1 0.5230(3) 0.7132(2) 0.62906(13) 0.0144(3) Uani d 1
C C2 0.3878(3) 0.8690(2) 0.63606(13) 0.0148(3) Uani d 1
C C3 0.3268(3) 0.9369(2) 0.72421(13) 0.0172(4) Uani d 1
C C4 0.3917(3) 0.8552(2) 0.80586(13) 0.0186(4) Uani d 1
H H4 0.3480 0.9029 0.8652 0.022 Uiso calc 1
C C5 0.5217(3) 0.7024(2) 0.80102(13) 0.0177(4) Uani d 1
C C6 0.5845(3) 0.6314(2) 0.71466(13) 0.0159(3) Uani d 1
C C7 0.5863(3) 0.6550(2) 0.53009(13) 0.0151(3) Uani d 1
C C8 0.8161(3) 0.4493(2) 0.42423(13) 0.0144(3) Uani d 1
C C9 0.9533(3) 0.2963(2) 0.43085(13) 0.0153(3) Uani d 1
C C10 1.0320(3) 0.2159(2) 0.34827(13) 0.0156(3) Uani d 1
C C11 0.9856(3) 0.2835(2) 0.25973(13) 0.0176(4) Uani d 1
H H11 1.0409 0.2269 0.2038 0.021 Uiso calc 1
C C12 0.8560(3) 0.4359(2) 0.25538(13) 0.0180(4) Uani d 1
C C13 0.7682(3) 0.5202(2) 0.33614(13) 0.0169(4) Uani d 1
H H13 0.6772 0.6241 0.3313 0.020 Uiso calc 1
O O1 0.3150(2) 0.95706(16) 0.56027(10) 0.0203(3) Uani d 1
H H1O 0.364(5) 0.893(4) 0.516(3) 0.062(10) Uiso d 1
O O2 0.4970(2) 0.73476(16) 0.46413(10) 0.0239(3) Uani d 1
O O3 0.9964(2) 0.24008(16) 0.51951(9) 0.0198(3) Uani d 1
H H3O 1.081(5) 0.154(4) 0.521(2) 0.053(9) Uiso d 1
N N1 0.7395(2) 0.51966(18) 0.51270(11) 0.0160(3) Uani d 1
H H1N 0.790(4) 0.470(3) 0.561(2) 0.033(7) Uiso d 1
Cl Cl1 0.17067(8) 1.12793(5) 0.72880(3) 0.02598(12) Uani d 1
Cl Cl2 0.60222(8) 0.60473(6) 0.90548(3) 0.02628(12) Uani d 1
Cl Cl3 0.73444(7) 0.43706(5) 0.71895(3) 0.02215(11) Uani d 1
Cl Cl4 1.19104(7) 0.02420(5) 0.35651(3) 0.02084(11) Uani d 1
Cl Cl5 0.80180(8) 0.52492(6) 0.14470(3) 0.02605(12) Uani d 1
C C14 -0.3506(4) 1.1013(3) 0.89580(17) 0.0377(6) Uani d 1
H H14A -0.4718 1.1673 0.9358 0.057 Uiso calc 1
H H14B -0.3751 1.0117 0.8799 0.057 Uiso calc 1
H H14C -0.3230 1.1592 0.8372 0.057 Uiso calc 1
C C15 -0.1685(3) 1.0486(3) 0.94909(14) 0.0258(4) Uani d 1
C C16 -0.0866(3) 0.8975(3) 0.98487(15) 0.0270(4) Uani d 1
H H16 -0.1453 0.8259 0.9749 0.032 Uiso calc 1
C C17 -0.0791(3) 1.1503(2) 0.96518(15) 0.0269(5) Uani d 1
H H17 -0.1323 1.2541 0.9416 0.032 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C6 C1 C2 . 116.97(16)
C6 C1 C7 . 127.53(16)
C2 C1 C7 . 115.49(16)
O1 C2 C3 . 117.32(16)
O1 C2 C1 . 122.45(16)
C3 C2 C1 . 120.22(17)
C4 C3 C2 . 121.40(17)
C4 C3 Cl1 . 119.88(14)
C2 C3 Cl1 . 118.71(15)
C3 C4 C5 . 119.44(17)
C3 C4 H4 . 120.3
C5 C4 H4 . 120.3
C4 C5 C6 . 120.58(17)
C4 C5 Cl2 . 117.80(14)
C6 C5 Cl2 . 121.62(15)
C5 C6 C1 . 121.34(17)
C5 C6 Cl3 . 116.23(14)
C1 C6 Cl3 . 122.40(14)
O2 C7 N1 . 120.21(17)
O2 C7 C1 . 119.29(16)
N1 C7 C1 . 120.50(16)
C13 C8 C9 . 120.50(16)
C13 C8 N1 . 125.32(16)
C9 C8 N1 . 114.17(16)
O3 C9 C10 . 125.64(17)
O3 C9 C8 . 115.85(16)
C10 C9 C8 . 118.50(17)
C11 C10 C9 . 122.09(17)
C11 C10 Cl4 . 119.07(14)
C9 C10 Cl4 . 118.84(15)
C12 C11 C10 . 117.86(17)
C12 C11 H11 . 121.1
C10 C11 H11 . 121.1
C11 C12 C13 . 122.35(18)
C11 C12 Cl5 . 118.72(14)
C13 C12 Cl5 . 118.93(15)
C12 C13 C8 . 118.61(17)
C12 C13 H13 . 120.7
C8 C13 H13 . 120.7
C2 O1 H1O . 102(2)
C9 O3 H3O . 114(2)
C7 N1 C8 . 127.27(17)
C7 N1 H1N . 115.4(19)
C8 N1 H1N . 117.2(19)
C15 C14 H14A . 109.5
C15 C14 H14B . 109.5
H14A C14 H14B . 109.5
C15 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
C17 C15 C16 . 117.9(2)
C17 C15 C14 . 120.9(2)
C16 C15 C14 . 121.2(2)
C17 C16 C15 2_577 121.2(2)
C17 C16 H16 2_577 119.4
C15 C16 H16 . 119.4
C16 C17 C15 2_577 121.0(2)
C16 C17 H17 2_577 119.5
C15 C17 H17 . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.415(3)
C1 C2 . 1.421(2)
C1 C7 . 1.505(2)
C2 O1 . 1.341(2)
C2 C3 . 1.400(2)
C3 C4 . 1.373(3)
C3 Cl1 . 1.7209(19)
C4 C5 . 1.387(3)
C4 H4 . 0.9500
C5 C6 . 1.390(3)
C5 Cl2 . 1.7304(19)
C6 Cl3 . 1.7353(19)
C7 O2 . 1.243(2)
C7 N1 . 1.342(2)
C8 C13 . 1.391(3)
C8 C9 . 1.405(3)
C8 N1 . 1.416(2)
C9 O3 . 1.357(2)
C9 C10 . 1.387(2)
C10 C11 . 1.386(3)
C10 Cl4 . 1.7339(19)
C11 C12 . 1.383(3)
C11 H11 . 0.9500
C12 C13 . 1.389(3)
C12 Cl5 . 1.7390(19)
C13 H13 . 0.9500
O1 H1O . 0.85(4)
O3 H3O . 0.81(3)
N1 H1N . 0.84(3)
C14 C15 . 1.509(3)
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 C17 . 1.390(3)
C15 C16 . 1.392(3)
C16 C17 2_577 1.387(3)
C16 H16 . 0.9500
C17 C16 2_577 1.387(3)
C17 H17 . 0.9500
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
O1 H1O Cl4 1_465 0.85(4) 2.73(3) 3.1154(15) 109(3)
O1 H1O O2 . 0.85(4) 1.61(4) 2.4309(19) 159(4)
O3 H3O Cl4 . 0.81(3) 2.63(3) 3.0438(14) 113(3)
O3 H3O O1 1_645 0.81(3) 2.07(3) 2.852(2) 163(3)
N1 H1N O3 . 0.84(3) 2.18(3) 2.578(2) 109(2)
N1 H1N Cl3 . 0.84(3) 2.23(3) 2.9599(17) 145(2)
C13 H13 O2 . 0.95 2.22 2.792(2) 118
C4 H4 Cg1 . 0.95 2.78 3.553(2) 139
C4 H4 Cg1 2_577 0.95 2.78 3.553(2) 139
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_4
_geom_torsion
C6 C1 C2 O1 . -178.31(16)
C7 C1 C2 O1 . 2.4(2)
C6 C1 C2 C3 . 2.2(3)
C7 C1 C2 C3 . -177.04(16)
O1 C2 C3 C4 . 179.21(17)
C1 C2 C3 C4 . -1.3(3)
O1 C2 C3 Cl1 . -1.9(2)
C1 C2 C3 Cl1 . 177.60(14)
C2 C3 C4 C5 . 0.5(3)
Cl1 C3 C4 C5 . -178.37(14)
C3 C4 C5 C6 . -0.7(3)
C3 C4 C5 Cl2 . 179.16(15)
C4 C5 C6 C1 . 1.8(3)
Cl2 C5 C6 C1 . -178.11(14)
C4 C5 C6 Cl3 . -176.23(15)
Cl2 C5 C6 Cl3 . 3.9(2)
C2 C1 C6 C5 . -2.5(3)
C7 C1 C6 C5 . 176.66(17)
C2 C1 C6 Cl3 . 175.41(13)
C7 C1 C6 Cl3 . -5.4(3)
C6 C1 C7 O2 . 170.25(18)
C2 C1 C7 O2 . -10.6(2)
C6 C1 C7 N1 . -10.8(3)
C2 C1 C7 N1 . 168.40(16)
C13 C8 C9 O3 . 177.31(16)
N1 C8 C9 O3 . -1.7(2)
C13 C8 C9 C10 . -2.9(3)
N1 C8 C9 C10 . 178.08(16)
O3 C9 C10 C11 . -177.76(17)
C8 C9 C10 C11 . 2.4(3)
O3 C9 C10 Cl4 . 3.0(3)
C8 C9 C10 Cl4 . -176.76(13)
C9 C10 C11 C12 . -0.1(3)
Cl4 C10 C11 C12 . 179.09(14)
C10 C11 C12 C13 . -1.9(3)
C10 C11 C12 Cl5 . 178.01(14)
C11 C12 C13 C8 . 1.5(3)
Cl5 C12 C13 C8 . -178.46(14)
C9 C8 C13 C12 . 1.0(3)
N1 C8 C13 C12 . 179.93(17)
O2 C7 N1 C8 . -1.3(3)
C1 C7 N1 C8 . 179.75(16)
C13 C8 N1 C7 . 11.3(3)
C9 C8 N1 C7 . -169.69(17)
C17 C15 C16 C17 2_577 -0.1(3)
C14 C15 C16 C17 2_577 -179.22(19)
C16 C15 C17 C16 2_577 0.1(3)
C14 C15 C17 C16 2_577 179.22(19)
