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Halogen–halogen contacts are electrostatic in nature and exhibit directionality similar to hydrogen bonds. Oxyclozanide [systematic name: 2,3,5-tri­chloro-N-(3,5-di­chloro-2-hy­droxy­phen­yl)-6-hy­droxy­benzamide] is a drug used for the treatment of fascioliasis in domestic animals. The mol­ecule carries five chlorine substituents and represents an ideal candidate for the study of halogen bonds in the crystal. Three new crystalline solvates of oxyclozanide, namely, oxyclozanide benzene hemisolvate, C13H6Cl5NO3·0.5C6H6, (I), oxyclozanide xylene hemisolvate, C13H6Cl5NO3·0.5C8H10, (II), and oxyclozanide toluene hemisolvate, C13H6Cl5NO3·0.5C7H8, (III), were structurally characterized. In this context, the crystal structure of oxyclozanide chloro­benzene hemisolvate, C13H6Cl5NO3·0.5C6H5Cl, (IV), was redetermined based on intensity data collected at 100 K. In all four solvates, the cocrystallized solvent mol­ecules are located on crystallographic inversion centres. Solvates (I)–(IV) exhibit similar one-dimensional hydrogen-bonded chains generated by O—H...O, O—H...Cl and Cl...Cl inter­actions. The extension of these one-dimensional chains into two-dimensional layers is promoted by Cl...Cl and C—H...π contacts. Solvates (III) and (IV) are isostructural and differ from (I) and (II) with respect to subtle details concerning the inter­molecular contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617015923/eg3229sup1.cif
Contains datablocks I, II, III, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015923/eg3229Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015923/eg3229IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015923/eg3229IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617015923/eg3229IVsup5.hkl
Contains datablock IV

CCDC references: 1583525; 1583524; 1583523; 1583522

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: Bruker SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: Bruker SHELXTL.

2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide benzene hemisolvate (I) top
Crystal data top
C13H6Cl5NO3·0.5C6H6Z = 2
Mr = 440.49F(000) = 442
Triclinic, P1Dx = 1.750 Mg m3
a = 7.16810 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.28821 (10) ÅCell parameters from 9832 reflections
c = 13.42132 (15) Åθ = 2.3–30.0°
α = 88.3124 (5)°µ = 0.88 mm1
β = 85.6481 (5)°T = 100 K
γ = 69.7508 (5)°Plate, colorless
V = 835.93 (2) Å30.28 × 0.12 × 0.12 mm
Data collection top
Bruker D8 QUEST PHOTON-100
diffractometer
4544 reflections with I > 2σ(I)
ω and φ scansRint = 0.042
Absorption correction: multi-scan
SADABS, Bruker, 2016
θmax = 30.6°, θmin = 2.3°
Tmin = 0.674, Tmax = 0.746h = 1010
33894 measured reflectionsk = 1313
5125 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.049P)2 + 1.7393P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
5125 reflectionsΔρmax = 1.01 e Å3
238 parametersΔρmin = 0.45 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7028 (3)0.6943 (3)0.62719 (16)0.0122 (4)
C20.6728 (3)0.8529 (3)0.63386 (17)0.0126 (4)
C30.6045 (3)0.9287 (2)0.72536 (17)0.0134 (4)
C40.5744 (3)0.8501 (3)0.81021 (17)0.0150 (4)
H40.52570.90320.87150.018*
C50.6155 (3)0.6926 (3)0.80567 (17)0.0141 (4)
C60.6786 (3)0.6156 (2)0.71628 (17)0.0128 (4)
C70.7569 (3)0.6285 (3)0.52377 (16)0.0127 (4)
C80.7720 (3)0.4220 (2)0.41010 (16)0.0122 (4)
C90.7888 (3)0.2662 (3)0.41558 (16)0.0125 (4)
C100.8438 (3)0.1793 (3)0.32880 (17)0.0133 (4)
C110.8740 (3)0.2434 (3)0.23666 (17)0.0137 (4)
H110.91090.18280.17780.016*
C120.8487 (3)0.3983 (3)0.23332 (16)0.0133 (4)
C130.7990 (3)0.4888 (3)0.31852 (17)0.0140 (4)
H130.78370.59450.31430.017*
N10.7236 (3)0.4999 (2)0.50233 (15)0.0131 (3)
H1N0.694 (5)0.457 (4)0.549 (3)0.028 (9)*
O10.7052 (3)0.9357 (2)0.55533 (13)0.0180 (3)
H1O0.753 (6)0.867 (5)0.512 (3)0.030 (10)*
O20.8234 (3)0.6981 (2)0.45756 (13)0.0198 (4)
O30.7510 (3)0.2153 (2)0.50785 (13)0.0175 (3)
H3O0.757 (6)0.122 (5)0.501 (3)0.040 (11)*
Cl10.55481 (9)1.12371 (6)0.73066 (5)0.01984 (13)
Cl20.58544 (9)0.59906 (7)0.91518 (4)0.01909 (13)
Cl30.73715 (9)0.41827 (6)0.71881 (4)0.01671 (12)
Cl40.87882 (9)0.01455 (6)0.33607 (4)0.01679 (12)
Cl50.88112 (10)0.48339 (7)0.11972 (4)0.02009 (13)
C141.0684 (5)0.1397 (3)0.0494 (2)0.0308 (6)
H141.11520.23540.08320.037*
C150.8740 (5)0.0836 (4)0.0203 (2)0.0312 (6)
H150.78780.14080.03430.037*
C160.8063 (5)0.0565 (4)0.0292 (2)0.0304 (6)
H160.67360.09510.04920.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0127 (9)0.0115 (9)0.0130 (9)0.0051 (7)0.0006 (7)0.0012 (7)
C20.0146 (9)0.0103 (9)0.0143 (10)0.0059 (8)0.0019 (7)0.0011 (7)
C30.0172 (10)0.0068 (9)0.0161 (10)0.0038 (7)0.0019 (8)0.0001 (7)
C40.0170 (10)0.0141 (10)0.0138 (10)0.0056 (8)0.0003 (8)0.0024 (8)
C50.0162 (10)0.0156 (10)0.0112 (9)0.0067 (8)0.0000 (7)0.0031 (8)
C60.0145 (9)0.0094 (9)0.0148 (10)0.0048 (7)0.0012 (7)0.0027 (7)
C70.0144 (9)0.0119 (9)0.0128 (9)0.0059 (8)0.0007 (7)0.0001 (7)
C80.0132 (9)0.0108 (9)0.0127 (9)0.0042 (7)0.0008 (7)0.0003 (7)
C90.0153 (9)0.0106 (9)0.0116 (9)0.0046 (7)0.0007 (7)0.0000 (7)
C100.0148 (10)0.0107 (9)0.0145 (10)0.0043 (8)0.0028 (7)0.0011 (7)
C110.0158 (10)0.0138 (10)0.0119 (9)0.0054 (8)0.0008 (7)0.0008 (7)
C120.0161 (10)0.0151 (10)0.0101 (9)0.0069 (8)0.0024 (7)0.0028 (7)
C130.0162 (10)0.0132 (10)0.0132 (10)0.0058 (8)0.0011 (8)0.0014 (8)
N10.0192 (9)0.0104 (8)0.0106 (8)0.0067 (7)0.0011 (7)0.0005 (6)
O10.0301 (9)0.0120 (8)0.0143 (8)0.0108 (7)0.0012 (7)0.0022 (6)
O20.0336 (10)0.0167 (8)0.0144 (8)0.0162 (7)0.0025 (7)0.0009 (6)
O30.0321 (9)0.0092 (7)0.0127 (8)0.0099 (7)0.0014 (6)0.0004 (6)
Cl10.0283 (3)0.0104 (2)0.0212 (3)0.0074 (2)0.0000 (2)0.00175 (19)
Cl20.0264 (3)0.0186 (3)0.0128 (2)0.0093 (2)0.0018 (2)0.00335 (19)
Cl30.0260 (3)0.0097 (2)0.0150 (2)0.0070 (2)0.00141 (19)0.00290 (17)
Cl40.0235 (3)0.0103 (2)0.0164 (2)0.00561 (19)0.00081 (19)0.00124 (18)
Cl50.0292 (3)0.0225 (3)0.0115 (2)0.0129 (2)0.0015 (2)0.00396 (19)
C140.0440 (17)0.0220 (13)0.0196 (12)0.0029 (12)0.0011 (11)0.0003 (10)
C150.0385 (16)0.0284 (14)0.0267 (14)0.0124 (12)0.0047 (12)0.0061 (11)
C160.0310 (14)0.0308 (15)0.0224 (13)0.0013 (12)0.0019 (11)0.0082 (11)
Geometric parameters (Å, º) top
C1—C61.414 (3)C9—C101.389 (3)
C1—C21.417 (3)C10—C111.391 (3)
C1—C71.502 (3)C10—Cl41.730 (2)
C2—O11.340 (3)C11—C121.387 (3)
C2—C31.402 (3)C11—H110.9500
C3—C41.378 (3)C12—C131.389 (3)
C3—Cl11.723 (2)C12—Cl51.734 (2)
C4—C51.391 (3)C13—H130.9500
C4—H40.9500N1—H1N0.78 (4)
C5—C61.378 (3)O1—H1O0.83 (4)
C5—Cl21.723 (2)O3—H3O0.86 (4)
C6—Cl31.733 (2)C14—C16i1.381 (5)
C7—O21.245 (3)C14—C151.390 (5)
C7—N11.340 (3)C14—H140.9500
C8—C131.391 (3)C15—C161.389 (5)
C8—C91.410 (3)C15—H150.9500
C8—N11.411 (3)C16—C14i1.381 (5)
C9—O31.354 (3)C16—H160.9500
C6—C1—C2117.9 (2)C9—C10—C11121.8 (2)
C6—C1—C7127.1 (2)C9—C10—Cl4118.95 (17)
C2—C1—C7115.07 (19)C11—C10—Cl4119.24 (17)
O1—C2—C3117.7 (2)C12—C11—C10118.0 (2)
O1—C2—C1122.7 (2)C12—C11—H11121.0
C3—C2—C1119.6 (2)C10—C11—H11121.0
C4—C3—C2121.0 (2)C11—C12—C13122.2 (2)
C4—C3—Cl1119.87 (18)C11—C12—Cl5119.51 (17)
C2—C3—Cl1119.09 (17)C13—C12—Cl5118.31 (17)
C3—C4—C5119.7 (2)C12—C13—C8118.9 (2)
C3—C4—H4120.2C12—C13—H13120.6
C5—C4—H4120.2C8—C13—H13120.6
C6—C5—C4120.6 (2)C7—N1—C8126.3 (2)
C6—C5—Cl2121.83 (18)C7—N1—H1N115 (3)
C4—C5—Cl2117.61 (17)C8—N1—H1N118 (3)
C5—C6—C1121.0 (2)C2—O1—H1O101 (3)
C5—C6—Cl3117.31 (17)C9—O3—H3O107 (3)
C1—C6—Cl3121.60 (17)C16i—C14—C15120.2 (3)
O2—C7—N1120.6 (2)C16i—C14—H14119.9
O2—C7—C1119.5 (2)C15—C14—H14119.9
N1—C7—C1119.76 (19)C16—C15—C14119.7 (3)
C13—C8—C9120.4 (2)C16—C15—H15120.2
C13—C8—N1124.8 (2)C14—C15—H15120.2
C9—C8—N1114.84 (19)C14i—C16—C15120.1 (3)
O3—C9—C10126.1 (2)C14i—C16—H16119.9
O3—C9—C8115.24 (19)C15—C16—H16119.9
C10—C9—C8118.6 (2)
C6—C1—C2—O1175.3 (2)C2—C1—C7—N1157.5 (2)
C7—C1—C2—O15.0 (3)C13—C8—C9—O3177.2 (2)
C6—C1—C2—C35.4 (3)N1—C8—C9—O31.7 (3)
C7—C1—C2—C3174.3 (2)C13—C8—C9—C103.6 (3)
O1—C2—C3—C4177.7 (2)N1—C8—C9—C10177.5 (2)
C1—C2—C3—C42.9 (3)O3—C9—C10—C11178.1 (2)
O1—C2—C3—Cl13.1 (3)C8—C9—C10—C112.8 (3)
C1—C2—C3—Cl1176.25 (17)O3—C9—C10—Cl42.8 (3)
C2—C3—C4—C51.1 (4)C8—C9—C10—Cl4176.31 (17)
Cl1—C3—C4—C5179.71 (18)C9—C10—C11—C120.3 (3)
C3—C4—C5—C62.6 (4)Cl4—C10—C11—C12178.73 (17)
C3—C4—C5—Cl2177.22 (18)C10—C11—C12—C131.4 (3)
C4—C5—C6—C10.1 (3)C10—C11—C12—Cl5178.98 (17)
Cl2—C5—C6—C1179.86 (17)C11—C12—C13—C80.6 (3)
C4—C5—C6—Cl3177.15 (18)Cl5—C12—C13—C8179.79 (17)
Cl2—C5—C6—Cl32.6 (3)C9—C8—C13—C121.9 (3)
C2—C1—C6—C54.0 (3)N1—C8—C13—C12179.2 (2)
C7—C1—C6—C5175.6 (2)O2—C7—N1—C85.6 (4)
C2—C1—C6—Cl3173.07 (17)C1—C7—N1—C8177.8 (2)
C7—C1—C6—Cl37.3 (3)C13—C8—N1—C722.8 (4)
C6—C1—C7—O2161.3 (2)C9—C8—N1—C7158.4 (2)
C2—C1—C7—O219.1 (3)C16i—C14—C15—C160.1 (5)
C6—C1—C7—N122.1 (3)C14—C15—C16—C14i0.1 (5)
Symmetry code: (i) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O20.83 (4)1.65 (4)2.453 (3)161 (4)
O1—H1O···Cl4ii0.83 (4)2.80 (4)3.1912 (18)111 (3)
O3—H3O···O1iii0.86 (4)2.00 (4)2.778 (2)150 (4)
O3—H3O···Cl40.86 (4)2.52 (4)3.0543 (18)121 (3)
N1—H1N···O30.78 (4)2.22 (4)2.581 (3)109 (3)
N1—H1N···Cl30.78 (4)2.33 (4)2.981 (2)142 (4)
C13—H13···O20.952.252.791 (3)115
C11—H11···Cg1iv0.952.873.820 (3)177
C11—H11···Cg1v0.952.873.820 (3)177
Symmetry codes: (ii) x, y+1, z; (iii) x, y1, z; (iv) x, y1, z1; (v) x+2, y+1, z+1.
2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide xylene hemisolvate (II) top
Crystal data top
C13H6Cl5NO3·C8H10Z = 2
Mr = 454.52F(000) = 458
Triclinic, P1Dx = 1.731 Mg m3
a = 7.12429 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.40484 (11) ÅCell parameters from 9941 reflections
c = 14.27988 (16) Åθ = 2.7–28.4°
α = 83.7014 (5)°µ = 0.85 mm1
β = 80.0916 (5)°T = 100 K
γ = 67.8388 (4)°Block, colorless
V = 871.84 (2) Å30.42 × 0.38 × 0.24 mm
Data collection top
Bruker D8 QUEST PHOTON-100
diffractometer
3962 reflections with I > 2σ(I)
ω and φ scansRint = 0.050
Absorption correction: multi-scan
SADABS, Bruker,2016
θmax = 28.4°, θmin = 2.3°
Tmin = 0.643, Tmax = 0.746h = 99
33198 measured reflectionsk = 1212
4370 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0255P)2 + 0.9635P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
4370 reflectionsΔρmax = 0.38 e Å3
248 parametersΔρmin = 0.39 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5230 (3)0.7132 (2)0.62906 (13)0.0144 (3)
C20.3878 (3)0.8690 (2)0.63606 (13)0.0148 (3)
C30.3268 (3)0.9369 (2)0.72421 (13)0.0172 (4)
C40.3917 (3)0.8552 (2)0.80586 (13)0.0186 (4)
H40.34800.90290.86520.022*
C50.5217 (3)0.7024 (2)0.80102 (13)0.0177 (4)
C60.5845 (3)0.6314 (2)0.71466 (13)0.0159 (3)
C70.5863 (3)0.6550 (2)0.53009 (13)0.0151 (3)
C80.8161 (3)0.4493 (2)0.42423 (13)0.0144 (3)
C90.9533 (3)0.2963 (2)0.43085 (13)0.0153 (3)
C101.0320 (3)0.2159 (2)0.34827 (13)0.0156 (3)
C110.9856 (3)0.2835 (2)0.25973 (13)0.0176 (4)
H111.04090.22690.20380.021*
C120.8560 (3)0.4359 (2)0.25538 (13)0.0180 (4)
C130.7682 (3)0.5202 (2)0.33614 (13)0.0169 (4)
H130.67720.62410.33130.020*
O10.3150 (2)0.95706 (16)0.56027 (10)0.0203 (3)
H1O0.364 (5)0.893 (4)0.516 (3)0.062 (10)*
O20.4970 (2)0.73476 (16)0.46413 (10)0.0239 (3)
O30.9964 (2)0.24008 (16)0.51951 (9)0.0198 (3)
H3O1.081 (5)0.154 (4)0.521 (2)0.053 (9)*
N10.7395 (2)0.51966 (18)0.51270 (11)0.0160 (3)
H1N0.790 (4)0.470 (3)0.561 (2)0.033 (7)*
Cl10.17067 (8)1.12793 (5)0.72880 (3)0.02598 (12)
Cl20.60222 (8)0.60473 (6)0.90548 (3)0.02628 (12)
Cl30.73444 (7)0.43706 (5)0.71895 (3)0.02215 (11)
Cl41.19104 (7)0.02420 (5)0.35651 (3)0.02084 (11)
Cl50.80180 (8)0.52492 (6)0.14470 (3)0.02605 (12)
C140.3506 (4)1.1013 (3)0.89580 (17)0.0377 (6)
H14A0.47181.16730.93580.057*
H14B0.37511.01170.87990.057*
H14C0.32301.15920.83720.057*
C150.1685 (3)1.0486 (3)0.94909 (14)0.0258 (4)
C160.0866 (3)0.8975 (3)0.98487 (15)0.0270 (4)
H160.14530.82590.97490.032*
C170.0791 (3)1.1503 (2)0.96518 (15)0.0269 (5)
H170.13231.25410.94160.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0117 (8)0.0151 (8)0.0167 (8)0.0057 (7)0.0005 (6)0.0027 (6)
C20.0133 (8)0.0143 (8)0.0167 (8)0.0059 (7)0.0013 (6)0.0021 (6)
C30.0170 (9)0.0134 (8)0.0199 (9)0.0060 (7)0.0034 (7)0.0037 (7)
C40.0211 (9)0.0190 (9)0.0172 (8)0.0101 (8)0.0030 (7)0.0058 (7)
C50.0171 (9)0.0197 (9)0.0163 (8)0.0077 (7)0.0001 (7)0.0006 (7)
C60.0126 (8)0.0150 (8)0.0187 (8)0.0044 (7)0.0017 (7)0.0033 (7)
C70.0134 (8)0.0143 (8)0.0187 (8)0.0070 (7)0.0010 (7)0.0033 (7)
C80.0130 (8)0.0139 (8)0.0168 (8)0.0059 (7)0.0011 (6)0.0046 (6)
C90.0147 (8)0.0164 (8)0.0154 (8)0.0072 (7)0.0002 (6)0.0018 (7)
C100.0124 (8)0.0138 (8)0.0197 (9)0.0043 (7)0.0023 (7)0.0052 (7)
C110.0167 (9)0.0208 (9)0.0160 (8)0.0083 (7)0.0022 (7)0.0050 (7)
C120.0179 (9)0.0219 (9)0.0155 (8)0.0095 (8)0.0001 (7)0.0019 (7)
C130.0176 (9)0.0149 (8)0.0181 (8)0.0067 (7)0.0004 (7)0.0011 (7)
O10.0234 (7)0.0141 (6)0.0165 (6)0.0007 (5)0.0015 (5)0.0017 (5)
O20.0245 (7)0.0207 (7)0.0175 (6)0.0027 (6)0.0032 (5)0.0042 (5)
O30.0231 (7)0.0151 (7)0.0156 (6)0.0006 (6)0.0023 (5)0.0024 (5)
N10.0178 (8)0.0136 (7)0.0144 (7)0.0031 (6)0.0011 (6)0.0032 (6)
Cl10.0349 (3)0.0134 (2)0.0228 (2)0.00356 (19)0.00454 (19)0.00526 (17)
Cl20.0288 (3)0.0278 (3)0.0168 (2)0.0037 (2)0.00399 (18)0.00176 (18)
Cl30.0230 (2)0.0170 (2)0.0186 (2)0.00080 (18)0.00124 (17)0.00141 (16)
Cl40.0222 (2)0.0151 (2)0.0207 (2)0.00219 (17)0.00143 (17)0.00613 (16)
Cl50.0306 (3)0.0273 (3)0.0161 (2)0.0070 (2)0.00225 (18)0.00116 (18)
C140.0332 (13)0.0486 (15)0.0256 (11)0.0077 (11)0.0027 (9)0.0079 (10)
C150.0263 (11)0.0305 (11)0.0149 (9)0.0059 (9)0.0049 (8)0.0068 (8)
C160.0319 (11)0.0274 (11)0.0212 (10)0.0128 (9)0.0071 (8)0.0088 (8)
C170.0317 (11)0.0215 (10)0.0204 (9)0.0054 (9)0.0067 (8)0.0035 (8)
Geometric parameters (Å, º) top
C1—C61.415 (3)C10—Cl41.7339 (19)
C1—C21.421 (2)C11—C121.383 (3)
C1—C71.505 (2)C11—H110.9500
C2—O11.341 (2)C12—C131.389 (3)
C2—C31.400 (2)C12—Cl51.7390 (19)
C3—C41.373 (3)C13—H130.9500
C3—Cl11.7209 (19)O1—H1O0.85 (4)
C4—C51.387 (3)O3—H3O0.81 (3)
C4—H40.9500N1—H1N0.84 (3)
C5—C61.390 (3)C14—C151.509 (3)
C5—Cl21.7304 (19)C14—H14A0.9800
C6—Cl31.7353 (19)C14—H14B0.9800
C7—O21.243 (2)C14—H14C0.9800
C7—N11.342 (2)C15—C171.390 (3)
C8—C131.391 (3)C15—C161.392 (3)
C8—C91.405 (3)C16—C17i1.387 (3)
C8—N11.416 (2)C16—H160.9500
C9—O31.357 (2)C17—C16i1.387 (3)
C9—C101.387 (2)C17—H170.9500
C10—C111.386 (3)
C6—C1—C2116.97 (16)C12—C11—C10117.86 (17)
C6—C1—C7127.53 (16)C12—C11—H11121.1
C2—C1—C7115.49 (16)C10—C11—H11121.1
O1—C2—C3117.32 (16)C11—C12—C13122.35 (18)
O1—C2—C1122.45 (16)C11—C12—Cl5118.72 (14)
C3—C2—C1120.22 (17)C13—C12—Cl5118.93 (15)
C4—C3—C2121.40 (17)C12—C13—C8118.61 (17)
C4—C3—Cl1119.88 (14)C12—C13—H13120.7
C2—C3—Cl1118.71 (15)C8—C13—H13120.7
C3—C4—C5119.44 (17)C2—O1—H1O102 (2)
C3—C4—H4120.3C9—O3—H3O114 (2)
C5—C4—H4120.3C7—N1—C8127.27 (17)
C4—C5—C6120.58 (17)C7—N1—H1N115.4 (19)
C4—C5—Cl2117.80 (14)C8—N1—H1N117.2 (19)
C6—C5—Cl2121.62 (15)C15—C14—H14A109.5
C5—C6—C1121.34 (17)C15—C14—H14B109.5
C5—C6—Cl3116.23 (14)H14A—C14—H14B109.5
C1—C6—Cl3122.40 (14)C15—C14—H14C109.5
O2—C7—N1120.21 (17)H14A—C14—H14C109.5
O2—C7—C1119.29 (16)H14B—C14—H14C109.5
N1—C7—C1120.50 (16)C17—C15—C16117.9 (2)
C13—C8—C9120.50 (16)C17—C15—C14120.9 (2)
C13—C8—N1125.32 (16)C16—C15—C14121.2 (2)
C9—C8—N1114.17 (16)C17i—C16—C15121.2 (2)
O3—C9—C10125.64 (17)C17i—C16—H16119.4
O3—C9—C8115.85 (16)C15—C16—H16119.4
C10—C9—C8118.50 (17)C16i—C17—C15121.0 (2)
C11—C10—C9122.09 (17)C16i—C17—H17119.5
C11—C10—Cl4119.07 (14)C15—C17—H17119.5
C9—C10—Cl4118.84 (15)
C6—C1—C2—O1178.31 (16)C13—C8—C9—O3177.31 (16)
C7—C1—C2—O12.4 (2)N1—C8—C9—O31.7 (2)
C6—C1—C2—C32.2 (3)C13—C8—C9—C102.9 (3)
C7—C1—C2—C3177.04 (16)N1—C8—C9—C10178.08 (16)
O1—C2—C3—C4179.21 (17)O3—C9—C10—C11177.76 (17)
C1—C2—C3—C41.3 (3)C8—C9—C10—C112.4 (3)
O1—C2—C3—Cl11.9 (2)O3—C9—C10—Cl43.0 (3)
C1—C2—C3—Cl1177.60 (14)C8—C9—C10—Cl4176.76 (13)
C2—C3—C4—C50.5 (3)C9—C10—C11—C120.1 (3)
Cl1—C3—C4—C5178.37 (14)Cl4—C10—C11—C12179.09 (14)
C3—C4—C5—C60.7 (3)C10—C11—C12—C131.9 (3)
C3—C4—C5—Cl2179.16 (15)C10—C11—C12—Cl5178.01 (14)
C4—C5—C6—C11.8 (3)C11—C12—C13—C81.5 (3)
Cl2—C5—C6—C1178.11 (14)Cl5—C12—C13—C8178.46 (14)
C4—C5—C6—Cl3176.23 (15)C9—C8—C13—C121.0 (3)
Cl2—C5—C6—Cl33.9 (2)N1—C8—C13—C12179.93 (17)
C2—C1—C6—C52.5 (3)O2—C7—N1—C81.3 (3)
C7—C1—C6—C5176.66 (17)C1—C7—N1—C8179.75 (16)
C2—C1—C6—Cl3175.41 (13)C13—C8—N1—C711.3 (3)
C7—C1—C6—Cl35.4 (3)C9—C8—N1—C7169.69 (17)
C6—C1—C7—O2170.25 (18)C17—C15—C16—C17i0.1 (3)
C2—C1—C7—O210.6 (2)C14—C15—C16—C17i179.22 (19)
C6—C1—C7—N110.8 (3)C16—C15—C17—C16i0.1 (3)
C2—C1—C7—N1168.40 (16)C14—C15—C17—C16i179.22 (19)
Symmetry code: (i) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···Cl4ii0.85 (4)2.73 (3)3.1154 (15)109 (3)
O1—H1O···O20.85 (4)1.61 (4)2.4309 (19)159 (4)
O3—H3O···Cl40.81 (3)2.63 (3)3.0438 (14)113 (3)
O3—H3O···O1iii0.81 (3)2.07 (3)2.852 (2)163 (3)
N1—H1N···O30.84 (3)2.18 (3)2.578 (2)109 (2)
N1—H1N···Cl30.84 (3)2.23 (3)2.9599 (17)145 (2)
C13—H13···O20.952.222.792 (2)118
C4—H4···Cg10.952.783.553 (2)139
C4—H4···Cg1i0.952.783.553 (2)139
Symmetry codes: (i) x, y+2, z+2; (ii) x1, y+1, z; (iii) x+1, y1, z.
2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide toluene hemisolvate (III) top
Crystal data top
C13H6Cl5NO3·0.5C7H8Z = 2
Mr = 447.50F(000) = 450
Triclinic, P1Dx = 1.739 Mg m3
a = 6.92017 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.71946 (11) ÅCell parameters from 9976 reflections
c = 13.98498 (17) Åθ = 2.3–27.5°
α = 86.3845 (5)°µ = 0.87 mm1
β = 85.4687 (5)°T = 100 K
γ = 65.8069 (5)°Block, colorless
V = 854.85 (2) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker D8 QUEST PHOTON-100
diffractometer
3596 reflections with I > 2σ(I)
ω and φ scansRint = 0.045
Absorption correction: multi-scan
SADABS; Bruker,2016
θmax = 27.6°, θmin = 2.3°
Tmin = 0.671, Tmax = 0.746h = 88
34326 measured reflectionsk = 1212
3926 independent reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.6449P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3926 reflectionsΔρmax = 0.70 e Å3
263 parametersΔρmin = 0.36 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5445 (3)0.70242 (19)0.63715 (13)0.0117 (3)
C20.4190 (3)0.8594 (2)0.64418 (13)0.0124 (3)
C30.3710 (3)0.9254 (2)0.73388 (13)0.0136 (4)
C40.4375 (3)0.8403 (2)0.81643 (13)0.0158 (4)
H40.40280.88670.87680.019*
C50.5556 (3)0.6861 (2)0.81126 (13)0.0145 (4)
C60.6090 (3)0.6169 (2)0.72352 (13)0.0127 (3)
C70.5976 (3)0.64568 (19)0.53671 (13)0.0118 (3)
C80.8190 (3)0.44060 (19)0.42960 (13)0.0115 (3)
C90.9544 (3)0.2859 (2)0.43545 (13)0.0124 (3)
C101.0224 (3)0.2073 (2)0.35111 (13)0.0130 (3)
C110.9688 (3)0.2788 (2)0.26193 (13)0.0145 (4)
H111.01620.22380.20470.017*
C120.8445 (3)0.4321 (2)0.25876 (13)0.0144 (4)
C130.7666 (3)0.5148 (2)0.34112 (13)0.0129 (3)
H130.67940.61980.33700.015*
O10.3444 (2)0.95046 (15)0.56754 (10)0.0170 (3)
H1O0.378 (5)0.896 (4)0.525 (2)0.045 (9)*
O20.5016 (2)0.72891 (15)0.46946 (10)0.0208 (3)
O31.0037 (2)0.22740 (16)0.52478 (10)0.0177 (3)
H3O1.090 (5)0.147 (3)0.526 (2)0.035 (8)*
N10.7519 (2)0.50897 (17)0.51940 (11)0.0126 (3)
H1N0.805 (4)0.455 (3)0.567 (2)0.037 (8)*
Cl10.22859 (8)1.11787 (5)0.73944 (3)0.02065 (13)
Cl20.63532 (8)0.58405 (5)0.91728 (3)0.02191 (13)
Cl30.74991 (7)0.42266 (5)0.72621 (3)0.01645 (12)
Cl41.17609 (7)0.01493 (5)0.35769 (3)0.01722 (12)
Cl50.78220 (8)0.52576 (6)0.14821 (3)0.02193 (13)
C140.2911 (13)1.0908 (11)0.9046 (6)0.049 (2)0.5
H14A0.39801.18700.92780.073*0.5
H14B0.34971.01420.91140.073*0.5
H14C0.25131.10330.83680.073*0.5
C150.0981 (6)1.0415 (4)0.9624 (3)0.0309 (10)0.5
C160.0081 (6)1.1429 (3)0.9749 (2)0.0305 (15)0.5
H160.06801.24180.94670.037*0.5
C170.1697 (6)1.0996 (4)1.0284 (3)0.0369 (11)0.5
H170.23121.16891.03690.044*0.5
C180.2574 (6)0.9548 (5)1.0695 (3)0.047 (3)0.5
H180.37890.92521.10610.056*0.5
C190.1674 (7)0.8534 (3)1.0571 (3)0.0450 (15)0.5
H190.22740.75441.08520.054*0.5
C200.0103 (7)0.8967 (4)1.0036 (3)0.0313 (15)0.5
H200.07180.82740.99510.038*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0112 (8)0.0113 (8)0.0123 (8)0.0045 (7)0.0003 (6)0.0013 (6)
C20.0113 (8)0.0129 (8)0.0118 (8)0.0038 (7)0.0002 (6)0.0002 (6)
C30.0139 (8)0.0101 (8)0.0154 (9)0.0036 (7)0.0025 (7)0.0027 (7)
C40.0176 (9)0.0162 (9)0.0125 (9)0.0058 (7)0.0017 (7)0.0039 (7)
C50.0158 (8)0.0175 (9)0.0107 (8)0.0073 (7)0.0016 (7)0.0009 (7)
C60.0119 (8)0.0105 (8)0.0139 (9)0.0029 (6)0.0005 (6)0.0002 (6)
C70.0115 (8)0.0118 (8)0.0128 (8)0.0054 (7)0.0004 (6)0.0014 (6)
C80.0123 (8)0.0114 (8)0.0109 (8)0.0048 (7)0.0005 (6)0.0023 (6)
C90.0122 (8)0.0130 (8)0.0120 (8)0.0053 (7)0.0004 (6)0.0003 (6)
C100.0124 (8)0.0107 (8)0.0155 (9)0.0041 (7)0.0013 (6)0.0032 (7)
C110.0148 (8)0.0178 (9)0.0115 (8)0.0071 (7)0.0013 (7)0.0040 (7)
C120.0161 (8)0.0172 (9)0.0106 (8)0.0078 (7)0.0001 (7)0.0007 (7)
C130.0130 (8)0.0116 (8)0.0132 (8)0.0043 (7)0.0004 (6)0.0004 (6)
O10.0222 (7)0.0105 (6)0.0114 (6)0.0001 (5)0.0005 (5)0.0003 (5)
O20.0250 (7)0.0146 (7)0.0113 (6)0.0041 (5)0.0028 (5)0.0010 (5)
O30.0225 (7)0.0116 (6)0.0112 (6)0.0012 (6)0.0015 (5)0.0007 (5)
N10.0147 (7)0.0111 (7)0.0096 (7)0.0025 (6)0.0020 (6)0.0001 (6)
Cl10.0273 (3)0.0100 (2)0.0185 (2)0.00167 (18)0.00269 (18)0.00386 (17)
Cl20.0298 (3)0.0195 (2)0.0107 (2)0.0040 (2)0.00335 (18)0.00140 (17)
Cl30.0204 (2)0.0104 (2)0.0130 (2)0.00089 (17)0.00071 (16)0.00092 (16)
Cl40.0195 (2)0.0108 (2)0.0169 (2)0.00156 (17)0.00101 (17)0.00391 (16)
Cl50.0290 (3)0.0221 (2)0.0104 (2)0.0064 (2)0.00104 (18)0.00198 (17)
C140.044 (4)0.064 (5)0.036 (4)0.017 (4)0.009 (3)0.026 (4)
C150.039 (3)0.034 (3)0.015 (2)0.011 (2)0.0107 (19)0.0097 (19)
C160.047 (4)0.018 (3)0.018 (3)0.007 (2)0.010 (2)0.003 (2)
C170.046 (3)0.040 (3)0.021 (2)0.014 (2)0.006 (2)0.012 (2)
C180.049 (5)0.055 (5)0.021 (4)0.006 (4)0.007 (3)0.009 (3)
C190.060 (4)0.024 (3)0.026 (3)0.004 (2)0.018 (3)0.005 (2)
C200.048 (4)0.020 (3)0.021 (3)0.012 (2)0.017 (2)0.001 (2)
Geometric parameters (Å, º) top
C1—C61.416 (3)C11—H110.9500
C1—C21.418 (2)C12—C131.388 (2)
C1—C71.504 (2)C12—Cl51.7353 (19)
C2—O11.339 (2)C13—H130.9500
C2—C31.399 (2)O1—H1O0.77 (3)
C3—C41.372 (3)O3—H3O0.77 (3)
C3—Cl11.7236 (18)N1—H1N0.83 (3)
C4—C51.385 (3)C14—C151.506 (9)
C4—H40.9500C14—H14A0.9800
C5—C61.387 (3)C14—H14B0.9800
C5—Cl21.7267 (19)C14—H14C0.9800
C6—Cl31.7332 (18)C15—C161.3900
C7—O21.242 (2)C15—C201.3900
C7—N11.342 (2)C16—C171.3900
C8—C131.388 (2)C16—H160.9500
C8—C91.410 (2)C17—C181.3900
C8—N11.412 (2)C17—H170.9500
C9—O31.349 (2)C18—C191.3900
C9—C101.388 (2)C18—H180.9500
C10—C111.389 (3)C19—C201.3900
C10—Cl41.7322 (18)C19—H190.9500
C11—C121.382 (3)C20—H200.9500
C6—C1—C2117.62 (16)C11—C12—Cl5119.23 (14)
C6—C1—C7127.06 (16)C13—C12—Cl5118.37 (14)
C2—C1—C7115.31 (15)C8—C13—C12118.49 (16)
O1—C2—C3117.23 (16)C8—C13—H13120.8
O1—C2—C1122.78 (16)C12—C13—H13120.8
C3—C2—C1119.98 (16)C2—O1—H1O104 (2)
C4—C3—C2121.19 (16)C9—O3—H3O113 (2)
C4—C3—Cl1119.95 (14)C7—N1—C8126.96 (16)
C2—C3—Cl1118.85 (14)C7—N1—H1N117 (2)
C3—C4—C5119.65 (17)C8—N1—H1N116 (2)
C3—C4—H4120.2C15—C14—H14A109.5
C5—C4—H4120.2C15—C14—H14B109.5
C4—C5—C6120.81 (17)H14A—C14—H14B109.5
C4—C5—Cl2117.80 (14)C15—C14—H14C109.5
C6—C5—Cl2121.39 (14)H14A—C14—H14C109.5
C5—C6—C1120.69 (16)H14B—C14—H14C109.5
C5—C6—Cl3116.70 (14)C16—C15—C20120.0
C1—C6—Cl3122.58 (14)C16—C15—C14119.2 (4)
O2—C7—N1120.31 (16)C20—C15—C14120.8 (4)
O2—C7—C1119.15 (16)C17—C16—C15120.0
N1—C7—C1120.49 (16)C17—C16—H16120.0
C13—C8—C9120.66 (16)C15—C16—H16120.0
C13—C8—N1125.12 (16)C16—C17—C18120.0
C9—C8—N1114.20 (16)C16—C17—H17120.0
O3—C9—C10125.93 (16)C18—C17—H17120.0
O3—C9—C8115.59 (15)C19—C18—C17120.0
C10—C9—C8118.47 (16)C19—C18—H18120.0
C9—C10—C11121.70 (17)C17—C18—H18120.0
C9—C10—Cl4118.99 (14)C20—C19—C18120.0
C11—C10—Cl4119.31 (14)C20—C19—H19120.0
C12—C11—C10118.14 (17)C18—C19—H19120.0
C12—C11—H11120.9C19—C20—C15120.0
C10—C11—H11120.9C19—C20—H20120.0
C11—C12—C13122.40 (17)C15—C20—H20120.0
C6—C1—C2—O1178.20 (16)C13—C8—C9—C104.2 (3)
C7—C1—C2—O12.8 (2)N1—C8—C9—C10177.61 (16)
C6—C1—C2—C32.8 (3)O3—C9—C10—C11177.77 (17)
C7—C1—C2—C3176.21 (16)C8—C9—C10—C113.1 (3)
O1—C2—C3—C4178.79 (16)O3—C9—C10—Cl42.8 (3)
C1—C2—C3—C42.1 (3)C8—C9—C10—Cl4176.29 (13)
O1—C2—C3—Cl12.1 (2)C9—C10—C11—C120.0 (3)
C1—C2—C3—Cl1176.99 (13)Cl4—C10—C11—C12179.43 (14)
C2—C3—C4—C50.4 (3)C10—C11—C12—C132.2 (3)
Cl1—C3—C4—C5178.70 (14)C10—C11—C12—Cl5177.83 (14)
C3—C4—C5—C60.6 (3)C9—C8—C13—C122.2 (3)
C3—C4—C5—Cl2179.97 (14)N1—C8—C13—C12179.86 (16)
C4—C5—C6—C10.2 (3)C11—C12—C13—C81.1 (3)
Cl2—C5—C6—C1179.27 (14)Cl5—C12—C13—C8178.96 (13)
C4—C5—C6—Cl3178.02 (14)O2—C7—N1—C82.5 (3)
Cl2—C5—C6—Cl32.5 (2)C1—C7—N1—C8179.82 (15)
C2—C1—C6—C51.8 (3)C13—C8—N1—C713.9 (3)
C7—C1—C6—C5177.04 (16)C9—C8—N1—C7168.07 (17)
C2—C1—C6—Cl3176.26 (13)C20—C15—C16—C170.0
C7—C1—C6—Cl34.9 (3)C14—C15—C16—C17179.7 (5)
C6—C1—C7—O2168.38 (17)C15—C16—C17—C180.0
C2—C1—C7—O212.7 (2)C16—C17—C18—C190.0
C6—C1—C7—N113.9 (3)C17—C18—C19—C200.0
C2—C1—C7—N1164.96 (16)C18—C19—C20—C150.0
C13—C8—C9—O3176.55 (16)C16—C15—C20—C190.0
N1—C8—C9—O31.6 (2)C14—C15—C20—C19179.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O20.77 (3)1.70 (3)2.4328 (19)157 (3)
O1—H1O···Cl4i0.77 (3)2.76 (3)3.1736 (15)116 (3)
O3—H3O···O1ii0.77 (3)2.09 (3)2.8247 (19)162 (3)
O3—H3O···Cl40.77 (3)2.65 (3)3.0491 (14)114 (3)
N1—H1N···O30.83 (3)2.16 (3)2.572 (2)110 (2)
N1—H1N···Cl30.83 (3)2.26 (3)2.9608 (16)143 (3)
C13—H13···O20.952.212.782 (2)118
C4—H4···Cg10.952.753.551 (3)143
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y1, z.
2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide chlorobenzene hemisolvate (IV) top
Crystal data top
C13H6Cl5NO3·0.5C6H5ClZ = 2
Mr = 457.71F(000) = 458
Triclinic, P1Dx = 1.785 Mg m3
a = 6.90927 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.69846 (10) ÅCell parameters from 9026 reflections
c = 13.97198 (15) Åθ = 2.7–30.5°
α = 86.5557 (5)°µ = 0.95 mm1
β = 85.9678 (5)°T = 100 K
γ = 65.8305 (5)°Block, colorless
V = 851.56 (2) Å30.32 × 0.22 × 0.13 mm
Data collection top
Bruker D8 QUEST PHOTON-100
diffractometer
4583 reflections with I > 2σ(I)
ω and φ scansRint = 0.039
Absorption correction: multi-scan
SADABS, Bruker,2016
θmax = 30.5°, θmin = 2.3°
Tmin = 0.609, Tmax = 0.746h = 99
28022 measured reflectionsk = 1313
5153 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0271P)2 + 0.6071P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
5153 reflectionsΔρmax = 0.47 e Å3
262 parametersΔρmin = 0.40 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5493 (2)0.69889 (14)0.63821 (9)0.0124 (2)
C20.4238 (2)0.85676 (15)0.64551 (10)0.0134 (2)
C30.3787 (2)0.92250 (15)0.73564 (10)0.0146 (2)
C40.4472 (2)0.83663 (15)0.81823 (10)0.0156 (3)
H40.41500.88300.87870.019*
C50.5641 (2)0.68135 (15)0.81268 (10)0.0145 (2)
C60.6145 (2)0.61251 (14)0.72444 (10)0.0133 (2)
C70.6001 (2)0.64288 (15)0.53757 (10)0.0132 (2)
C80.8213 (2)0.43816 (15)0.42989 (9)0.0127 (2)
C90.9564 (2)0.28285 (15)0.43559 (10)0.0131 (2)
C101.0236 (2)0.20416 (15)0.35099 (10)0.0136 (2)
C110.9688 (2)0.27606 (15)0.26157 (10)0.0144 (2)
H111.01540.22120.20430.017*
C120.8442 (2)0.43010 (15)0.25871 (10)0.0147 (2)
C130.7673 (2)0.51275 (15)0.34127 (10)0.0140 (2)
H130.67960.61790.33720.017*
O10.34808 (17)0.94815 (11)0.56887 (8)0.0177 (2)
H1O0.387 (4)0.887 (3)0.5250 (19)0.046 (7)*
O20.50180 (18)0.72605 (12)0.47023 (8)0.0209 (2)
O31.00771 (18)0.22409 (12)0.52514 (7)0.0178 (2)
H3O1.092 (4)0.140 (3)0.5255 (18)0.039 (6)*
N10.75516 (19)0.50592 (13)0.51990 (8)0.0136 (2)
H1N0.811 (3)0.448 (2)0.5671 (15)0.025 (5)*
Cl10.23748 (6)1.11544 (4)0.74163 (3)0.02096 (8)
Cl20.64438 (6)0.57877 (4)0.91872 (2)0.02178 (8)
Cl30.75269 (6)0.41765 (4)0.72676 (2)0.01719 (8)
Cl41.17772 (6)0.01160 (4)0.35736 (2)0.01750 (8)
Cl50.77895 (6)0.52445 (4)0.14820 (2)0.02178 (8)
C140.0900 (4)1.0315 (3)0.9659 (2)0.0260 (7)0.5
C150.0078 (4)1.1389 (2)0.97452 (18)0.0239 (9)0.5
H150.07481.23670.94510.029*0.5
C160.1722 (4)1.1034 (3)1.02614 (18)0.0282 (7)0.5
H160.22841.17681.03200.034*0.5
C170.2702 (4)0.9603 (3)1.06916 (18)0.0316 (11)0.5
H170.39330.93601.10440.038*0.5
C180.1880 (4)0.8528 (2)1.06057 (18)0.0351 (9)0.5
H180.25500.75511.09000.042*0.5
C190.0079 (5)0.8884 (3)1.0089 (2)0.0325 (11)0.5
H190.04820.81501.00310.039*0.5
Cl60.3135 (2)1.07814 (16)0.90176 (9)0.0407 (3)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0122 (6)0.0106 (5)0.0131 (6)0.0035 (5)0.0008 (4)0.0007 (4)
C20.0135 (6)0.0110 (6)0.0143 (6)0.0038 (5)0.0006 (4)0.0000 (4)
C30.0152 (6)0.0100 (5)0.0166 (6)0.0030 (5)0.0002 (5)0.0021 (5)
C40.0174 (6)0.0134 (6)0.0150 (6)0.0051 (5)0.0005 (5)0.0026 (5)
C50.0161 (6)0.0138 (6)0.0128 (6)0.0051 (5)0.0017 (5)0.0004 (5)
C60.0134 (6)0.0096 (5)0.0152 (6)0.0029 (5)0.0012 (5)0.0001 (4)
C70.0125 (6)0.0120 (6)0.0150 (6)0.0047 (5)0.0002 (4)0.0015 (4)
C80.0135 (6)0.0111 (5)0.0128 (6)0.0042 (5)0.0006 (4)0.0020 (4)
C90.0127 (6)0.0114 (5)0.0145 (6)0.0043 (5)0.0014 (4)0.0003 (4)
C100.0127 (6)0.0102 (5)0.0170 (6)0.0034 (5)0.0004 (5)0.0024 (5)
C110.0146 (6)0.0150 (6)0.0140 (6)0.0063 (5)0.0004 (5)0.0025 (5)
C120.0164 (6)0.0153 (6)0.0125 (6)0.0066 (5)0.0010 (5)0.0006 (5)
C130.0145 (6)0.0110 (5)0.0151 (6)0.0039 (5)0.0009 (5)0.0002 (4)
O10.0217 (5)0.0101 (4)0.0150 (5)0.0003 (4)0.0009 (4)0.0006 (4)
O20.0242 (5)0.0143 (5)0.0148 (5)0.0022 (4)0.0035 (4)0.0002 (4)
O30.0217 (5)0.0103 (4)0.0141 (5)0.0013 (4)0.0029 (4)0.0003 (4)
N10.0159 (5)0.0094 (5)0.0124 (5)0.0017 (4)0.0022 (4)0.0008 (4)
Cl10.02598 (18)0.01007 (14)0.02078 (16)0.00128 (12)0.00118 (13)0.00281 (11)
Cl20.02931 (19)0.01755 (16)0.01339 (15)0.00417 (14)0.00417 (13)0.00169 (12)
Cl30.02126 (16)0.00969 (14)0.01533 (15)0.00100 (12)0.00173 (11)0.00117 (11)
Cl40.01932 (16)0.01024 (14)0.01891 (16)0.00172 (12)0.00009 (12)0.00291 (11)
Cl50.02782 (19)0.02052 (16)0.01319 (15)0.00618 (14)0.00201 (12)0.00215 (12)
C140.0319 (17)0.0290 (17)0.0185 (14)0.0139 (14)0.0076 (12)0.0094 (12)
C150.035 (2)0.0153 (15)0.0193 (17)0.0088 (15)0.0071 (15)0.0042 (14)
C160.0372 (19)0.0265 (16)0.0223 (15)0.0139 (14)0.0036 (13)0.0090 (12)
C170.036 (2)0.033 (2)0.0132 (19)0.0017 (18)0.0022 (15)0.0026 (15)
C180.050 (2)0.0225 (16)0.0233 (16)0.0068 (16)0.0082 (15)0.0023 (13)
C190.047 (3)0.025 (2)0.028 (2)0.0186 (19)0.0142 (18)0.0045 (17)
Cl60.0365 (6)0.0541 (8)0.0347 (7)0.0198 (6)0.0001 (5)0.0163 (5)
Geometric parameters (Å, º) top
C1—C61.4149 (18)C11—C121.3853 (19)
C1—C21.4233 (18)C11—H110.9500
C1—C71.5039 (18)C12—C131.3897 (18)
C2—O11.3382 (16)C12—Cl51.7365 (14)
C2—C31.4028 (18)C13—H130.9500
C3—C41.3740 (19)O1—H1O0.83 (3)
C3—Cl11.7242 (13)O3—H3O0.78 (3)
C4—C51.3912 (18)N1—H1N0.84 (2)
C4—H40.9500C14—C151.3900
C5—C61.3912 (18)C14—C191.3900
C5—Cl21.7260 (14)C14—Cl61.722 (2)
C6—Cl31.7331 (13)C15—C161.3900
C7—O21.2439 (17)C15—H150.9500
C7—N11.3453 (17)C16—C171.3900
C8—C131.3900 (18)C16—H160.9500
C8—C91.4111 (18)C17—C181.3900
C8—N11.4124 (17)C17—H170.9500
C9—O31.3517 (16)C18—C191.3900
C9—C101.3916 (18)C18—H180.9500
C10—C111.3914 (19)C19—H190.9500
C10—Cl41.7305 (13)
C6—C1—C2117.67 (12)C12—C11—H11121.0
C6—C1—C7127.14 (12)C10—C11—H11121.0
C2—C1—C7115.19 (11)C11—C12—C13122.51 (13)
O1—C2—C3117.50 (12)C11—C12—Cl5119.17 (10)
O1—C2—C1122.64 (12)C13—C12—Cl5118.32 (10)
C3—C2—C1119.85 (12)C12—C13—C8118.55 (12)
C4—C3—C2121.33 (12)C12—C13—H13120.7
C4—C3—Cl1119.85 (10)C8—C13—H13120.7
C2—C3—Cl1118.81 (10)C2—O1—H1O101.6 (18)
C3—C4—C5119.53 (12)C9—O3—H3O112.9 (18)
C3—C4—H4120.2C7—N1—C8127.01 (12)
C5—C4—H4120.2C7—N1—H1N118.2 (14)
C4—C5—C6120.75 (12)C8—N1—H1N114.3 (14)
C4—C5—Cl2117.59 (10)C15—C14—C19120.0
C6—C5—Cl2121.66 (10)C15—C14—Cl6119.20 (16)
C5—C6—C1120.79 (12)C19—C14—Cl6120.80 (16)
C5—C6—Cl3116.63 (10)C16—C15—C14120.0
C1—C6—Cl3122.56 (10)C16—C15—H15120.0
O2—C7—N1120.11 (13)C14—C15—H15120.0
O2—C7—C1119.45 (12)C15—C16—C17120.0
N1—C7—C1120.41 (12)C15—C16—H16120.0
C13—C8—C9120.58 (12)C17—C16—H16120.0
C13—C8—N1125.30 (12)C18—C17—C16120.0
C9—C8—N1114.10 (12)C18—C17—H17120.0
O3—C9—C10125.95 (12)C16—C17—H17120.0
O3—C9—C8115.48 (12)C17—C18—C19120.0
C10—C9—C8118.56 (12)C17—C18—H18120.0
C11—C10—C9121.73 (12)C19—C18—H18120.0
C11—C10—Cl4119.21 (10)C18—C19—C14120.0
C9—C10—Cl4119.06 (10)C18—C19—H19120.0
C12—C11—C10117.93 (12)C14—C19—H19120.0
C6—C1—C2—O1177.86 (13)C13—C8—C9—C103.9 (2)
C7—C1—C2—O12.85 (19)N1—C8—C9—C10177.42 (12)
C6—C1—C2—C33.4 (2)O3—C9—C10—C11177.45 (13)
C7—C1—C2—C3175.92 (12)C8—C9—C10—C113.0 (2)
O1—C2—C3—C4178.92 (13)O3—C9—C10—Cl43.0 (2)
C1—C2—C3—C42.2 (2)C8—C9—C10—Cl4176.60 (10)
O1—C2—C3—Cl12.03 (18)C9—C10—C11—C120.0 (2)
C1—C2—C3—Cl1176.80 (10)Cl4—C10—C11—C12179.62 (10)
C2—C3—C4—C50.1 (2)C10—C11—C12—C132.3 (2)
Cl1—C3—C4—C5178.93 (11)C10—C11—C12—Cl5178.25 (10)
C3—C4—C5—C60.8 (2)C11—C12—C13—C81.4 (2)
C3—C4—C5—Cl2179.50 (11)Cl5—C12—C13—C8179.18 (10)
C4—C5—C6—C10.4 (2)C9—C8—C13—C121.8 (2)
Cl2—C5—C6—C1179.24 (11)N1—C8—C13—C12179.68 (13)
C4—C5—C6—Cl3177.82 (11)O2—C7—N1—C82.0 (2)
Cl2—C5—C6—Cl32.51 (17)C1—C7—N1—C8179.87 (12)
C2—C1—C6—C52.5 (2)C13—C8—N1—C713.7 (2)
C7—C1—C6—C5176.70 (13)C9—C8—N1—C7167.68 (13)
C2—C1—C6—Cl3175.65 (10)C19—C14—C15—C160.0
C7—C1—C6—Cl35.2 (2)Cl6—C14—C15—C16179.9 (2)
C6—C1—C7—O2167.43 (14)C14—C15—C16—C170.0
C2—C1—C7—O213.36 (19)C15—C16—C17—C180.0
C6—C1—C7—N114.6 (2)C16—C17—C18—C190.0
C2—C1—C7—N1164.56 (13)C17—C18—C19—C140.0
C13—C8—C9—O3176.47 (12)C15—C14—C19—C180.0
N1—C8—C9—O32.20 (18)Cl6—C14—C19—C18179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···Cl4i0.83 (3)2.78 (3)3.1898 (11)112 (2)
O1—H1O···O20.83 (3)1.64 (3)2.4382 (15)160 (3)
O3—H3O···Cl40.78 (3)2.64 (2)3.0550 (11)115 (2)
O3—H3O···O1ii0.78 (3)2.07 (3)2.8139 (14)159 (2)
N1—H1N···Cl30.84 (2)2.26 (2)2.9656 (12)141 (2)
N1—H1N···O30.84 (2)2.13 (2)2.5709 (15)112 (2)
C13—H13···O20.952.222.7869 (17)118
C4—H4···Cg10.952.763.5578 (18)142
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y1, z.
Details of ππ and Cl···Cl contacts (Å) observed in solvates (I)–(IV). top
Contacts(I)(II)(III)(IV)
ππv*3.8554 (14)3.6139 (13)3.6365 (12)3.6382 (9)
ππiv*3.6369 (14)4.2077 (13)3.9763 (12)3.9401 (9)
Cl3···Cl1ii3.4113 (8)3.3727 (7)3.4304 (7)3.4407 (6)
Cl2···Cl5vi3.5094 (9)-3.4059 (6)3.3522 (4)
Cl2···Cl2vii3.3107 (8)3.5964 (7)3.5884 (7)3.5938 (5)
Cl2···Cl5iv/-/v/v3.6262 (10)-3.6599 (8)3.6505 (6)
Cl5···Cl5viii/-/-/-3.5779 (8)---
Cl4···O2ii3.2124 (19)3.2065 (15)3.1814 (14)3.1724 (12)
θ1#145.88 (6)/131.79 (9)155.83 (8)148.65 (8)/156.05 (7)146.96 (5)/155.75 (5)
θ2#147.71 (8)/132.80 (9)156.66 (8)148.51 (8)/157.53 (7)147.16 (5)/157.66 (5)
Symmetry codes: (ii) x, y-1, z for (I); (ii) x+1, y-1, z for (II)–(IV); (iv) -x+2, -y+1, -z+1 for (I)–(IV); (v) -x+1, -y+1, -z+1 for (I)–(IV); (vi) x, y, z+1 for (I), (III) and (IV); (vii) -x+1, -y+1, -z+2 for (I)–(IV); (viii) -x+2, -y+1, -z for (I).

Notes: (*) centroid–centroid separation between the rings defined by C1–C6 and C8–C13 in the oxyclozanide molecule. (#) θ1 = C6–Cl3···Cl1/C5–Cl2···Cl5 and θ2 = C3—Cl1···Cl3/C12—Cl5···Cl2.
 

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