Role of halogen–halogen contacts in the crystal structures of three new solvates of the drug oxyclozanide

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.

Computing details

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)

Crystal data

C13H6Cl5NO3·0.5C6H6	Z = 2
Mr = 440.49	F(000) = 442
Triclinic, P1	Dx = 1.750 Mg m^−3
a = 7.16810 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.28821 (10) Å	Cell parameters from 9832 reflections
c = 13.42132 (15) Å	θ = 2.3–30.0°
α = 88.3124 (5)°	µ = 0.88 mm^−1
β = 85.6481 (5)°	T = 100 K
γ = 69.7508 (5)°	Plate, colorless
V = 835.93 (2) Å^3	0.28 × 0.12 × 0.12 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4544 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.042
Absorption correction: multi-scan SADABS, Bruker, 2016	θmax = 30.6°, θmin = 2.3°
Tmin = 0.674, Tmax = 0.746	h = −10→10
33894 measured reflections	k = −13→13
5125 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 1.7393P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.001
5125 reflections	Δρmax = 1.01 e Å^−3
238 parameters	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7028 (3)	0.6943 (3)	0.62719 (16)	0.0122 (4)
C2	0.6728 (3)	0.8529 (3)	0.63386 (17)	0.0126 (4)
C3	0.6045 (3)	0.9287 (2)	0.72536 (17)	0.0134 (4)
C4	0.5744 (3)	0.8501 (3)	0.81021 (17)	0.0150 (4)
H4	0.5257	0.9032	0.8715	0.018*
C5	0.6155 (3)	0.6926 (3)	0.80567 (17)	0.0141 (4)
C6	0.6786 (3)	0.6156 (2)	0.71628 (17)	0.0128 (4)
C7	0.7569 (3)	0.6285 (3)	0.52377 (16)	0.0127 (4)
C8	0.7720 (3)	0.4220 (2)	0.41010 (16)	0.0122 (4)
C9	0.7888 (3)	0.2662 (3)	0.41558 (16)	0.0125 (4)
C10	0.8438 (3)	0.1793 (3)	0.32880 (17)	0.0133 (4)
C11	0.8740 (3)	0.2434 (3)	0.23666 (17)	0.0137 (4)
H11	0.9109	0.1828	0.1778	0.016*
C12	0.8487 (3)	0.3983 (3)	0.23332 (16)	0.0133 (4)
C13	0.7990 (3)	0.4888 (3)	0.31852 (17)	0.0140 (4)
H13	0.7837	0.5945	0.3143	0.017*
N1	0.7236 (3)	0.4999 (2)	0.50233 (15)	0.0131 (3)
H1N	0.694 (5)	0.457 (4)	0.549 (3)	0.028 (9)*
O1	0.7052 (3)	0.9357 (2)	0.55533 (13)	0.0180 (3)
H1O	0.753 (6)	0.867 (5)	0.512 (3)	0.030 (10)*
O2	0.8234 (3)	0.6981 (2)	0.45756 (13)	0.0198 (4)
O3	0.7510 (3)	0.2153 (2)	0.50785 (13)	0.0175 (3)
H3O	0.757 (6)	0.122 (5)	0.501 (3)	0.040 (11)*
Cl1	0.55481 (9)	1.12371 (6)	0.73066 (5)	0.01984 (13)
Cl2	0.58544 (9)	0.59906 (7)	0.91518 (4)	0.01909 (13)
Cl3	0.73715 (9)	0.41827 (6)	0.71881 (4)	0.01671 (12)
Cl4	0.87882 (9)	−0.01455 (6)	0.33607 (4)	0.01679 (12)
Cl5	0.88112 (10)	0.48339 (7)	0.11972 (4)	0.02009 (13)
C14	1.0684 (5)	−0.1397 (3)	0.0494 (2)	0.0308 (6)
H14	1.1152	−0.2354	0.0832	0.037*
C15	0.8740 (5)	−0.0836 (4)	0.0203 (2)	0.0312 (6)
H15	0.7878	−0.1408	0.0343	0.037*
C16	0.8063 (5)	0.0565 (4)	−0.0292 (2)	0.0304 (6)
H16	0.6736	0.0951	−0.0492	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0127 (9)	0.0115 (9)	0.0130 (9)	−0.0051 (7)	−0.0006 (7)	0.0012 (7)
C2	0.0146 (9)	0.0103 (9)	0.0143 (10)	−0.0059 (8)	−0.0019 (7)	0.0011 (7)
C3	0.0172 (10)	0.0068 (9)	0.0161 (10)	−0.0038 (7)	−0.0019 (8)	0.0001 (7)
C4	0.0170 (10)	0.0141 (10)	0.0138 (10)	−0.0056 (8)	0.0003 (8)	−0.0024 (8)
C5	0.0162 (10)	0.0156 (10)	0.0112 (9)	−0.0067 (8)	0.0000 (7)	0.0031 (8)
C6	0.0145 (9)	0.0094 (9)	0.0148 (10)	−0.0048 (7)	−0.0012 (7)	0.0027 (7)
C7	0.0144 (9)	0.0119 (9)	0.0128 (9)	−0.0059 (8)	−0.0007 (7)	−0.0001 (7)
C8	0.0132 (9)	0.0108 (9)	0.0127 (9)	−0.0042 (7)	−0.0008 (7)	−0.0003 (7)
C9	0.0153 (9)	0.0106 (9)	0.0116 (9)	−0.0046 (7)	−0.0007 (7)	0.0000 (7)
C10	0.0148 (10)	0.0107 (9)	0.0145 (10)	−0.0043 (8)	−0.0028 (7)	0.0011 (7)
C11	0.0158 (10)	0.0138 (10)	0.0119 (9)	−0.0054 (8)	−0.0008 (7)	−0.0008 (7)
C12	0.0161 (10)	0.0151 (10)	0.0101 (9)	−0.0069 (8)	−0.0024 (7)	0.0028 (7)
C13	0.0162 (10)	0.0132 (10)	0.0132 (10)	−0.0058 (8)	−0.0011 (8)	0.0014 (8)
N1	0.0192 (9)	0.0104 (8)	0.0106 (8)	−0.0067 (7)	0.0011 (7)	−0.0005 (6)
O1	0.0301 (9)	0.0120 (8)	0.0143 (8)	−0.0108 (7)	−0.0012 (7)	0.0022 (6)
O2	0.0336 (10)	0.0167 (8)	0.0144 (8)	−0.0162 (7)	0.0025 (7)	−0.0009 (6)
O3	0.0321 (9)	0.0092 (7)	0.0127 (8)	−0.0099 (7)	0.0014 (6)	0.0004 (6)
Cl1	0.0283 (3)	0.0104 (2)	0.0212 (3)	−0.0074 (2)	0.0000 (2)	−0.00175 (19)
Cl2	0.0264 (3)	0.0186 (3)	0.0128 (2)	−0.0093 (2)	0.0018 (2)	0.00335 (19)
Cl3	0.0260 (3)	0.0097 (2)	0.0150 (2)	−0.0070 (2)	−0.00141 (19)	0.00290 (17)
Cl4	0.0235 (3)	0.0103 (2)	0.0164 (2)	−0.00561 (19)	−0.00081 (19)	−0.00124 (18)
Cl5	0.0292 (3)	0.0225 (3)	0.0115 (2)	−0.0129 (2)	−0.0015 (2)	0.00396 (19)
C14	0.0440 (17)	0.0220 (13)	0.0196 (12)	−0.0029 (12)	−0.0011 (11)	−0.0003 (10)
C15	0.0385 (16)	0.0284 (14)	0.0267 (14)	−0.0124 (12)	0.0047 (12)	−0.0061 (11)
C16	0.0310 (14)	0.0308 (15)	0.0224 (13)	−0.0013 (12)	−0.0019 (11)	−0.0082 (11)

Geometric parameters (Å, º)

C1—C6	1.414 (3)	C9—C10	1.389 (3)
C1—C2	1.417 (3)	C10—C11	1.391 (3)
C1—C7	1.502 (3)	C10—Cl4	1.730 (2)
C2—O1	1.340 (3)	C11—C12	1.387 (3)
C2—C3	1.402 (3)	C11—H11	0.9500
C3—C4	1.378 (3)	C12—C13	1.389 (3)
C3—Cl1	1.723 (2)	C12—Cl5	1.734 (2)
C4—C5	1.391 (3)	C13—H13	0.9500
C4—H4	0.9500	N1—H1N	0.78 (4)
C5—C6	1.378 (3)	O1—H1O	0.83 (4)
C5—Cl2	1.723 (2)	O3—H3O	0.86 (4)
C6—Cl3	1.733 (2)	C14—C16^i	1.381 (5)
C7—O2	1.245 (3)	C14—C15	1.390 (5)
C7—N1	1.340 (3)	C14—H14	0.9500
C8—C13	1.391 (3)	C15—C16	1.389 (5)
C8—C9	1.410 (3)	C15—H15	0.9500
C8—N1	1.411 (3)	C16—C14^i	1.381 (5)
C9—O3	1.354 (3)	C16—H16	0.9500
C6—C1—C2	117.9 (2)	C9—C10—C11	121.8 (2)
C6—C1—C7	127.1 (2)	C9—C10—Cl4	118.95 (17)
C2—C1—C7	115.07 (19)	C11—C10—Cl4	119.24 (17)
O1—C2—C3	117.7 (2)	C12—C11—C10	118.0 (2)
O1—C2—C1	122.7 (2)	C12—C11—H11	121.0
C3—C2—C1	119.6 (2)	C10—C11—H11	121.0
C4—C3—C2	121.0 (2)	C11—C12—C13	122.2 (2)
C4—C3—Cl1	119.87 (18)	C11—C12—Cl5	119.51 (17)
C2—C3—Cl1	119.09 (17)	C13—C12—Cl5	118.31 (17)
C3—C4—C5	119.7 (2)	C12—C13—C8	118.9 (2)
C3—C4—H4	120.2	C12—C13—H13	120.6
C5—C4—H4	120.2	C8—C13—H13	120.6
C6—C5—C4	120.6 (2)	C7—N1—C8	126.3 (2)
C6—C5—Cl2	121.83 (18)	C7—N1—H1N	115 (3)
C4—C5—Cl2	117.61 (17)	C8—N1—H1N	118 (3)
C5—C6—C1	121.0 (2)	C2—O1—H1O	101 (3)
C5—C6—Cl3	117.31 (17)	C9—O3—H3O	107 (3)
C1—C6—Cl3	121.60 (17)	C16^i—C14—C15	120.2 (3)
O2—C7—N1	120.6 (2)	C16^i—C14—H14	119.9
O2—C7—C1	119.5 (2)	C15—C14—H14	119.9
N1—C7—C1	119.76 (19)	C16—C15—C14	119.7 (3)
C13—C8—C9	120.4 (2)	C16—C15—H15	120.2
C13—C8—N1	124.8 (2)	C14—C15—H15	120.2
C9—C8—N1	114.84 (19)	C14^i—C16—C15	120.1 (3)
O3—C9—C10	126.1 (2)	C14^i—C16—H16	119.9
O3—C9—C8	115.24 (19)	C15—C16—H16	119.9
C10—C9—C8	118.6 (2)
C6—C1—C2—O1	175.3 (2)	C2—C1—C7—N1	−157.5 (2)
C7—C1—C2—O1	−5.0 (3)	C13—C8—C9—O3	−177.2 (2)
C6—C1—C2—C3	−5.4 (3)	N1—C8—C9—O3	1.7 (3)
C7—C1—C2—C3	174.3 (2)	C13—C8—C9—C10	3.6 (3)
O1—C2—C3—C4	−177.7 (2)	N1—C8—C9—C10	−177.5 (2)
C1—C2—C3—C4	2.9 (3)	O3—C9—C10—C11	178.1 (2)
O1—C2—C3—Cl1	3.1 (3)	C8—C9—C10—C11	−2.8 (3)
C1—C2—C3—Cl1	−176.25 (17)	O3—C9—C10—Cl4	−2.8 (3)
C2—C3—C4—C5	1.1 (4)	C8—C9—C10—Cl4	176.31 (17)
Cl1—C3—C4—C5	−179.71 (18)	C9—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	−2.6 (4)	Cl4—C10—C11—C12	−178.73 (17)
C3—C4—C5—Cl2	177.22 (18)	C10—C11—C12—C13	1.4 (3)
C4—C5—C6—C1	−0.1 (3)	C10—C11—C12—Cl5	−178.98 (17)
Cl2—C5—C6—C1	−179.86 (17)	C11—C12—C13—C8	−0.6 (3)
C4—C5—C6—Cl3	177.15 (18)	Cl5—C12—C13—C8	179.79 (17)
Cl2—C5—C6—Cl3	−2.6 (3)	C9—C8—C13—C12	−1.9 (3)
C2—C1—C6—C5	4.0 (3)	N1—C8—C13—C12	179.2 (2)
C7—C1—C6—C5	−175.6 (2)	O2—C7—N1—C8	5.6 (4)
C2—C1—C6—Cl3	−173.07 (17)	C1—C7—N1—C8	−177.8 (2)
C7—C1—C6—Cl3	7.3 (3)	C13—C8—N1—C7	−22.8 (4)
C6—C1—C7—O2	−161.3 (2)	C9—C8—N1—C7	158.4 (2)
C2—C1—C7—O2	19.1 (3)	C16^i—C14—C15—C16	0.1 (5)
C6—C1—C7—N1	22.1 (3)	C14—C15—C16—C14^i	−0.1 (5)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.83 (4)	1.65 (4)	2.453 (3)	161 (4)
O1—H1O···Cl4^ii	0.83 (4)	2.80 (4)	3.1912 (18)	111 (3)
O3—H3O···O1^iii	0.86 (4)	2.00 (4)	2.778 (2)	150 (4)
O3—H3O···Cl4	0.86 (4)	2.52 (4)	3.0543 (18)	121 (3)
N1—H1N···O3	0.78 (4)	2.22 (4)	2.581 (3)	109 (3)
N1—H1N···Cl3	0.78 (4)	2.33 (4)	2.981 (2)	142 (4)
C13—H13···O2	0.95	2.25	2.791 (3)	115
C11—H11···Cg1^iv	0.95	2.87	3.820 (3)	177
C11—H11···Cg1^v	0.95	2.87	3.820 (3)	177

Symmetry codes: (ii) x, y+1, z; (iii) x, y−1, z; (iv) x, y−1, z−1; (v) −x+2, −y+1, −z+1.

2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide xylene hemisolvate (II)

Crystal data

C13H6Cl5NO3·C8H10	Z = 2
Mr = 454.52	F(000) = 458
Triclinic, P1	Dx = 1.731 Mg m^−3
a = 7.12429 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.40484 (11) Å	Cell parameters from 9941 reflections
c = 14.27988 (16) Å	θ = 2.7–28.4°
α = 83.7014 (5)°	µ = 0.85 mm^−1
β = 80.0916 (5)°	T = 100 K
γ = 67.8388 (4)°	Block, colorless
V = 871.84 (2) Å^3	0.42 × 0.38 × 0.24 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	3962 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.050
Absorption correction: multi-scan SADABS, Bruker,2016	θmax = 28.4°, θmin = 2.3°
Tmin = 0.643, Tmax = 0.746	h = −9→9
33198 measured reflections	k = −12→12
4370 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 0.9635P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
4370 reflections	Δρmax = 0.38 e Å^−3
248 parameters	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5230 (3)	0.7132 (2)	0.62906 (13)	0.0144 (3)
C2	0.3878 (3)	0.8690 (2)	0.63606 (13)	0.0148 (3)
C3	0.3268 (3)	0.9369 (2)	0.72421 (13)	0.0172 (4)
C4	0.3917 (3)	0.8552 (2)	0.80586 (13)	0.0186 (4)
H4	0.3480	0.9029	0.8652	0.022*
C5	0.5217 (3)	0.7024 (2)	0.80102 (13)	0.0177 (4)
C6	0.5845 (3)	0.6314 (2)	0.71466 (13)	0.0159 (3)
C7	0.5863 (3)	0.6550 (2)	0.53009 (13)	0.0151 (3)
C8	0.8161 (3)	0.4493 (2)	0.42423 (13)	0.0144 (3)
C9	0.9533 (3)	0.2963 (2)	0.43085 (13)	0.0153 (3)
C10	1.0320 (3)	0.2159 (2)	0.34827 (13)	0.0156 (3)
C11	0.9856 (3)	0.2835 (2)	0.25973 (13)	0.0176 (4)
H11	1.0409	0.2269	0.2038	0.021*
C12	0.8560 (3)	0.4359 (2)	0.25538 (13)	0.0180 (4)
C13	0.7682 (3)	0.5202 (2)	0.33614 (13)	0.0169 (4)
H13	0.6772	0.6241	0.3313	0.020*
O1	0.3150 (2)	0.95706 (16)	0.56027 (10)	0.0203 (3)
H1O	0.364 (5)	0.893 (4)	0.516 (3)	0.062 (10)*
O2	0.4970 (2)	0.73476 (16)	0.46413 (10)	0.0239 (3)
O3	0.9964 (2)	0.24008 (16)	0.51951 (9)	0.0198 (3)
H3O	1.081 (5)	0.154 (4)	0.521 (2)	0.053 (9)*
N1	0.7395 (2)	0.51966 (18)	0.51270 (11)	0.0160 (3)
H1N	0.790 (4)	0.470 (3)	0.561 (2)	0.033 (7)*
Cl1	0.17067 (8)	1.12793 (5)	0.72880 (3)	0.02598 (12)
Cl2	0.60222 (8)	0.60473 (6)	0.90548 (3)	0.02628 (12)
Cl3	0.73444 (7)	0.43706 (5)	0.71895 (3)	0.02215 (11)
Cl4	1.19104 (7)	0.02420 (5)	0.35651 (3)	0.02084 (11)
Cl5	0.80180 (8)	0.52492 (6)	0.14470 (3)	0.02605 (12)
C14	−0.3506 (4)	1.1013 (3)	0.89580 (17)	0.0377 (6)
H14A	−0.4718	1.1673	0.9358	0.057*
H14B	−0.3751	1.0117	0.8799	0.057*
H14C	−0.3230	1.1592	0.8372	0.057*
C15	−0.1685 (3)	1.0486 (3)	0.94909 (14)	0.0258 (4)
C16	−0.0866 (3)	0.8975 (3)	0.98487 (15)	0.0270 (4)
H16	−0.1453	0.8259	0.9749	0.032*
C17	−0.0791 (3)	1.1503 (2)	0.96518 (15)	0.0269 (5)
H17	−0.1323	1.2541	0.9416	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0117 (8)	0.0151 (8)	0.0167 (8)	−0.0057 (7)	0.0005 (6)	−0.0027 (6)
C2	0.0133 (8)	0.0143 (8)	0.0167 (8)	−0.0059 (7)	0.0013 (6)	−0.0021 (6)
C3	0.0170 (9)	0.0134 (8)	0.0199 (9)	−0.0060 (7)	0.0034 (7)	−0.0037 (7)
C4	0.0211 (9)	0.0190 (9)	0.0172 (8)	−0.0101 (8)	0.0030 (7)	−0.0058 (7)
C5	0.0171 (9)	0.0197 (9)	0.0163 (8)	−0.0077 (7)	−0.0001 (7)	−0.0006 (7)
C6	0.0126 (8)	0.0150 (8)	0.0187 (8)	−0.0044 (7)	0.0017 (7)	−0.0033 (7)
C7	0.0134 (8)	0.0143 (8)	0.0187 (8)	−0.0070 (7)	0.0010 (7)	−0.0033 (7)
C8	0.0130 (8)	0.0139 (8)	0.0168 (8)	−0.0059 (7)	0.0011 (6)	−0.0046 (6)
C9	0.0147 (8)	0.0164 (8)	0.0154 (8)	−0.0072 (7)	0.0002 (6)	−0.0018 (7)
C10	0.0124 (8)	0.0138 (8)	0.0197 (9)	−0.0043 (7)	0.0023 (7)	−0.0052 (7)
C11	0.0167 (9)	0.0208 (9)	0.0160 (8)	−0.0083 (7)	0.0022 (7)	−0.0050 (7)
C12	0.0179 (9)	0.0219 (9)	0.0155 (8)	−0.0095 (8)	−0.0001 (7)	−0.0019 (7)
C13	0.0176 (9)	0.0149 (8)	0.0181 (8)	−0.0067 (7)	−0.0004 (7)	−0.0011 (7)
O1	0.0234 (7)	0.0141 (6)	0.0165 (6)	−0.0007 (5)	0.0015 (5)	−0.0017 (5)
O2	0.0245 (7)	0.0207 (7)	0.0175 (6)	0.0027 (6)	−0.0032 (5)	−0.0042 (5)
O3	0.0231 (7)	0.0151 (7)	0.0156 (6)	−0.0006 (6)	−0.0023 (5)	−0.0024 (5)
N1	0.0178 (8)	0.0136 (7)	0.0144 (7)	−0.0031 (6)	−0.0011 (6)	−0.0032 (6)
Cl1	0.0349 (3)	0.0134 (2)	0.0228 (2)	−0.00356 (19)	0.00454 (19)	−0.00526 (17)
Cl2	0.0288 (3)	0.0278 (3)	0.0168 (2)	−0.0037 (2)	−0.00399 (18)	−0.00176 (18)
Cl3	0.0230 (2)	0.0170 (2)	0.0186 (2)	0.00080 (18)	−0.00124 (17)	−0.00141 (16)
Cl4	0.0222 (2)	0.0151 (2)	0.0207 (2)	−0.00219 (17)	0.00143 (17)	−0.00613 (16)
Cl5	0.0306 (3)	0.0273 (3)	0.0161 (2)	−0.0070 (2)	−0.00225 (18)	0.00116 (18)
C14	0.0332 (13)	0.0486 (15)	0.0256 (11)	−0.0077 (11)	−0.0027 (9)	−0.0079 (10)
C15	0.0263 (11)	0.0305 (11)	0.0149 (9)	−0.0059 (9)	0.0049 (8)	−0.0068 (8)
C16	0.0319 (11)	0.0274 (11)	0.0212 (10)	−0.0128 (9)	0.0071 (8)	−0.0088 (8)
C17	0.0317 (11)	0.0215 (10)	0.0204 (9)	−0.0054 (9)	0.0067 (8)	−0.0035 (8)

Geometric parameters (Å, º)

C1—C6	1.415 (3)	C10—Cl4	1.7339 (19)
C1—C2	1.421 (2)	C11—C12	1.383 (3)
C1—C7	1.505 (2)	C11—H11	0.9500
C2—O1	1.341 (2)	C12—C13	1.389 (3)
C2—C3	1.400 (2)	C12—Cl5	1.7390 (19)
C3—C4	1.373 (3)	C13—H13	0.9500
C3—Cl1	1.7209 (19)	O1—H1O	0.85 (4)
C4—C5	1.387 (3)	O3—H3O	0.81 (3)
C4—H4	0.9500	N1—H1N	0.84 (3)
C5—C6	1.390 (3)	C14—C15	1.509 (3)
C5—Cl2	1.7304 (19)	C14—H14A	0.9800
C6—Cl3	1.7353 (19)	C14—H14B	0.9800
C7—O2	1.243 (2)	C14—H14C	0.9800
C7—N1	1.342 (2)	C15—C17	1.390 (3)
C8—C13	1.391 (3)	C15—C16	1.392 (3)
C8—C9	1.405 (3)	C16—C17^i	1.387 (3)
C8—N1	1.416 (2)	C16—H16	0.9500
C9—O3	1.357 (2)	C17—C16^i	1.387 (3)
C9—C10	1.387 (2)	C17—H17	0.9500
C10—C11	1.386 (3)
C6—C1—C2	116.97 (16)	C12—C11—C10	117.86 (17)
C6—C1—C7	127.53 (16)	C12—C11—H11	121.1
C2—C1—C7	115.49 (16)	C10—C11—H11	121.1
O1—C2—C3	117.32 (16)	C11—C12—C13	122.35 (18)
O1—C2—C1	122.45 (16)	C11—C12—Cl5	118.72 (14)
C3—C2—C1	120.22 (17)	C13—C12—Cl5	118.93 (15)
C4—C3—C2	121.40 (17)	C12—C13—C8	118.61 (17)
C4—C3—Cl1	119.88 (14)	C12—C13—H13	120.7
C2—C3—Cl1	118.71 (15)	C8—C13—H13	120.7
C3—C4—C5	119.44 (17)	C2—O1—H1O	102 (2)
C3—C4—H4	120.3	C9—O3—H3O	114 (2)
C5—C4—H4	120.3	C7—N1—C8	127.27 (17)
C4—C5—C6	120.58 (17)	C7—N1—H1N	115.4 (19)
C4—C5—Cl2	117.80 (14)	C8—N1—H1N	117.2 (19)
C6—C5—Cl2	121.62 (15)	C15—C14—H14A	109.5
C5—C6—C1	121.34 (17)	C15—C14—H14B	109.5
C5—C6—Cl3	116.23 (14)	H14A—C14—H14B	109.5
C1—C6—Cl3	122.40 (14)	C15—C14—H14C	109.5
O2—C7—N1	120.21 (17)	H14A—C14—H14C	109.5
O2—C7—C1	119.29 (16)	H14B—C14—H14C	109.5
N1—C7—C1	120.50 (16)	C17—C15—C16	117.9 (2)
C13—C8—C9	120.50 (16)	C17—C15—C14	120.9 (2)
C13—C8—N1	125.32 (16)	C16—C15—C14	121.2 (2)
C9—C8—N1	114.17 (16)	C17^i—C16—C15	121.2 (2)
O3—C9—C10	125.64 (17)	C17^i—C16—H16	119.4
O3—C9—C8	115.85 (16)	C15—C16—H16	119.4
C10—C9—C8	118.50 (17)	C16^i—C17—C15	121.0 (2)
C11—C10—C9	122.09 (17)	C16^i—C17—H17	119.5
C11—C10—Cl4	119.07 (14)	C15—C17—H17	119.5
C9—C10—Cl4	118.84 (15)
C6—C1—C2—O1	−178.31 (16)	C13—C8—C9—O3	177.31 (16)
C7—C1—C2—O1	2.4 (2)	N1—C8—C9—O3	−1.7 (2)
C6—C1—C2—C3	2.2 (3)	C13—C8—C9—C10	−2.9 (3)
C7—C1—C2—C3	−177.04 (16)	N1—C8—C9—C10	178.08 (16)
O1—C2—C3—C4	179.21 (17)	O3—C9—C10—C11	−177.76 (17)
C1—C2—C3—C4	−1.3 (3)	C8—C9—C10—C11	2.4 (3)
O1—C2—C3—Cl1	−1.9 (2)	O3—C9—C10—Cl4	3.0 (3)
C1—C2—C3—Cl1	177.60 (14)	C8—C9—C10—Cl4	−176.76 (13)
C2—C3—C4—C5	0.5 (3)	C9—C10—C11—C12	−0.1 (3)
Cl1—C3—C4—C5	−178.37 (14)	Cl4—C10—C11—C12	179.09 (14)
C3—C4—C5—C6	−0.7 (3)	C10—C11—C12—C13	−1.9 (3)
C3—C4—C5—Cl2	179.16 (15)	C10—C11—C12—Cl5	178.01 (14)
C4—C5—C6—C1	1.8 (3)	C11—C12—C13—C8	1.5 (3)
Cl2—C5—C6—C1	−178.11 (14)	Cl5—C12—C13—C8	−178.46 (14)
C4—C5—C6—Cl3	−176.23 (15)	C9—C8—C13—C12	1.0 (3)
Cl2—C5—C6—Cl3	3.9 (2)	N1—C8—C13—C12	179.93 (17)
C2—C1—C6—C5	−2.5 (3)	O2—C7—N1—C8	−1.3 (3)
C7—C1—C6—C5	176.66 (17)	C1—C7—N1—C8	179.75 (16)
C2—C1—C6—Cl3	175.41 (13)	C13—C8—N1—C7	11.3 (3)
C7—C1—C6—Cl3	−5.4 (3)	C9—C8—N1—C7	−169.69 (17)
C6—C1—C7—O2	170.25 (18)	C17—C15—C16—C17^i	−0.1 (3)
C2—C1—C7—O2	−10.6 (2)	C14—C15—C16—C17^i	−179.22 (19)
C6—C1—C7—N1	−10.8 (3)	C16—C15—C17—C16^i	0.1 (3)
C2—C1—C7—N1	168.40 (16)	C14—C15—C17—C16^i	179.22 (19)

Symmetry code: (i) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl4^ii	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^iii	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^i	0.95	2.78	3.553 (2)	139

Symmetry codes: (i) −x, −y+2, −z+2; (ii) x−1, y+1, z; (iii) x+1, y−1, z.

2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide toluene hemisolvate (III)

Crystal data

C13H6Cl5NO3·0.5C7H8	Z = 2
Mr = 447.50	F(000) = 450
Triclinic, P1	Dx = 1.739 Mg m^−3
a = 6.92017 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.71946 (11) Å	Cell parameters from 9976 reflections
c = 13.98498 (17) Å	θ = 2.3–27.5°
α = 86.3845 (5)°	µ = 0.87 mm^−1
β = 85.4687 (5)°	T = 100 K
γ = 65.8069 (5)°	Block, colorless
V = 854.85 (2) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	3596 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.045
Absorption correction: multi-scan SADABS; Bruker,2016	θmax = 27.6°, θmin = 2.3°
Tmin = 0.671, Tmax = 0.746	h = −8→8
34326 measured reflections	k = −12→12
3926 independent reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.6449P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3926 reflections	Δρmax = 0.70 e Å^−3
263 parameters	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5445 (3)	0.70242 (19)	0.63715 (13)	0.0117 (3)
C2	0.4190 (3)	0.8594 (2)	0.64418 (13)	0.0124 (3)
C3	0.3710 (3)	0.9254 (2)	0.73388 (13)	0.0136 (4)
C4	0.4375 (3)	0.8403 (2)	0.81643 (13)	0.0158 (4)
H4	0.4028	0.8867	0.8768	0.019*
C5	0.5556 (3)	0.6861 (2)	0.81126 (13)	0.0145 (4)
C6	0.6090 (3)	0.6169 (2)	0.72352 (13)	0.0127 (3)
C7	0.5976 (3)	0.64568 (19)	0.53671 (13)	0.0118 (3)
C8	0.8190 (3)	0.44060 (19)	0.42960 (13)	0.0115 (3)
C9	0.9544 (3)	0.2859 (2)	0.43545 (13)	0.0124 (3)
C10	1.0224 (3)	0.2073 (2)	0.35111 (13)	0.0130 (3)
C11	0.9688 (3)	0.2788 (2)	0.26193 (13)	0.0145 (4)
H11	1.0162	0.2238	0.2047	0.017*
C12	0.8445 (3)	0.4321 (2)	0.25876 (13)	0.0144 (4)
C13	0.7666 (3)	0.5148 (2)	0.34112 (13)	0.0129 (3)
H13	0.6794	0.6198	0.3370	0.015*
O1	0.3444 (2)	0.95046 (15)	0.56754 (10)	0.0170 (3)
H1O	0.378 (5)	0.896 (4)	0.525 (2)	0.045 (9)*
O2	0.5016 (2)	0.72891 (15)	0.46946 (10)	0.0208 (3)
O3	1.0037 (2)	0.22740 (16)	0.52478 (10)	0.0177 (3)
H3O	1.090 (5)	0.147 (3)	0.526 (2)	0.035 (8)*
N1	0.7519 (2)	0.50897 (17)	0.51940 (11)	0.0126 (3)
H1N	0.805 (4)	0.455 (3)	0.567 (2)	0.037 (8)*
Cl1	0.22859 (8)	1.11787 (5)	0.73944 (3)	0.02065 (13)
Cl2	0.63532 (8)	0.58405 (5)	0.91728 (3)	0.02191 (13)
Cl3	0.74991 (7)	0.42266 (5)	0.72621 (3)	0.01645 (12)
Cl4	1.17609 (7)	0.01493 (5)	0.35769 (3)	0.01722 (12)
Cl5	0.78220 (8)	0.52576 (6)	0.14821 (3)	0.02193 (13)
C14	−0.2911 (13)	1.0908 (11)	0.9046 (6)	0.049 (2)	0.5
H14A	−0.3980	1.1870	0.9278	0.073*	0.5
H14B	−0.3497	1.0142	0.9114	0.073*	0.5
H14C	−0.2513	1.1033	0.8368	0.073*	0.5
C15	−0.0981 (6)	1.0415 (4)	0.9624 (3)	0.0309 (10)	0.5
C16	−0.0081 (6)	1.1429 (3)	0.9749 (2)	0.0305 (15)	0.5
H16	−0.0680	1.2418	0.9467	0.037*	0.5
C17	0.1697 (6)	1.0996 (4)	1.0284 (3)	0.0369 (11)	0.5
H17	0.2312	1.1689	1.0369	0.044*	0.5
C18	0.2574 (6)	0.9548 (5)	1.0695 (3)	0.047 (3)	0.5
H18	0.3789	0.9252	1.1061	0.056*	0.5
C19	0.1674 (7)	0.8534 (3)	1.0571 (3)	0.0450 (15)	0.5
H19	0.2274	0.7544	1.0852	0.054*	0.5
C20	−0.0103 (7)	0.8967 (4)	1.0036 (3)	0.0313 (15)	0.5
H20	−0.0718	0.8274	0.9951	0.038*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0112 (8)	0.0113 (8)	0.0123 (8)	−0.0045 (7)	0.0003 (6)	−0.0013 (6)
C2	0.0113 (8)	0.0129 (8)	0.0118 (8)	−0.0038 (7)	−0.0002 (6)	0.0002 (6)
C3	0.0139 (8)	0.0101 (8)	0.0154 (9)	−0.0036 (7)	0.0025 (7)	−0.0027 (7)
C4	0.0176 (9)	0.0162 (9)	0.0125 (9)	−0.0058 (7)	0.0017 (7)	−0.0039 (7)
C5	0.0158 (8)	0.0175 (9)	0.0107 (8)	−0.0073 (7)	−0.0016 (7)	0.0009 (7)
C6	0.0119 (8)	0.0105 (8)	0.0139 (9)	−0.0029 (6)	−0.0005 (6)	0.0002 (6)
C7	0.0115 (8)	0.0118 (8)	0.0128 (8)	−0.0054 (7)	0.0004 (6)	−0.0014 (6)
C8	0.0123 (8)	0.0114 (8)	0.0109 (8)	−0.0048 (7)	0.0005 (6)	−0.0023 (6)
C9	0.0122 (8)	0.0130 (8)	0.0120 (8)	−0.0053 (7)	−0.0004 (6)	−0.0003 (6)
C10	0.0124 (8)	0.0107 (8)	0.0155 (9)	−0.0041 (7)	0.0013 (6)	−0.0032 (7)
C11	0.0148 (8)	0.0178 (9)	0.0115 (8)	−0.0071 (7)	0.0013 (7)	−0.0040 (7)
C12	0.0161 (8)	0.0172 (9)	0.0106 (8)	−0.0078 (7)	−0.0001 (7)	0.0007 (7)
C13	0.0130 (8)	0.0116 (8)	0.0132 (8)	−0.0043 (7)	−0.0004 (6)	0.0004 (6)
O1	0.0222 (7)	0.0105 (6)	0.0114 (6)	−0.0001 (5)	0.0005 (5)	−0.0003 (5)
O2	0.0250 (7)	0.0146 (7)	0.0113 (6)	0.0041 (5)	−0.0028 (5)	−0.0010 (5)
O3	0.0225 (7)	0.0116 (6)	0.0112 (6)	0.0012 (6)	−0.0015 (5)	−0.0007 (5)
N1	0.0147 (7)	0.0111 (7)	0.0096 (7)	−0.0025 (6)	−0.0020 (6)	−0.0001 (6)
Cl1	0.0273 (3)	0.0100 (2)	0.0185 (2)	−0.00167 (18)	0.00269 (18)	−0.00386 (17)
Cl2	0.0298 (3)	0.0195 (2)	0.0107 (2)	−0.0040 (2)	−0.00335 (18)	0.00140 (17)
Cl3	0.0204 (2)	0.0104 (2)	0.0130 (2)	−0.00089 (17)	−0.00071 (16)	0.00092 (16)
Cl4	0.0195 (2)	0.0108 (2)	0.0169 (2)	−0.00156 (17)	0.00101 (17)	−0.00391 (16)
Cl5	0.0290 (3)	0.0221 (2)	0.0104 (2)	−0.0064 (2)	−0.00104 (18)	0.00198 (17)
C14	0.044 (4)	0.064 (5)	0.036 (4)	−0.017 (4)	0.009 (3)	−0.026 (4)
C15	0.039 (3)	0.034 (3)	0.015 (2)	−0.011 (2)	0.0107 (19)	−0.0097 (19)
C16	0.047 (4)	0.018 (3)	0.018 (3)	−0.007 (2)	0.010 (2)	−0.003 (2)
C17	0.046 (3)	0.040 (3)	0.021 (2)	−0.014 (2)	0.006 (2)	−0.012 (2)
C18	0.049 (5)	0.055 (5)	0.021 (4)	−0.006 (4)	0.007 (3)	−0.009 (3)
C19	0.060 (4)	0.024 (3)	0.026 (3)	0.004 (2)	0.018 (3)	0.005 (2)
C20	0.048 (4)	0.020 (3)	0.021 (3)	−0.012 (2)	0.017 (2)	−0.001 (2)

Geometric parameters (Å, º)

C1—C6	1.416 (3)	C11—H11	0.9500
C1—C2	1.418 (2)	C12—C13	1.388 (2)
C1—C7	1.504 (2)	C12—Cl5	1.7353 (19)
C2—O1	1.339 (2)	C13—H13	0.9500
C2—C3	1.399 (2)	O1—H1O	0.77 (3)
C3—C4	1.372 (3)	O3—H3O	0.77 (3)
C3—Cl1	1.7236 (18)	N1—H1N	0.83 (3)
C4—C5	1.385 (3)	C14—C15	1.506 (9)
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.387 (3)	C14—H14B	0.9800
C5—Cl2	1.7267 (19)	C14—H14C	0.9800
C6—Cl3	1.7332 (18)	C15—C16	1.3900
C7—O2	1.242 (2)	C15—C20	1.3900
C7—N1	1.342 (2)	C16—C17	1.3900
C8—C13	1.388 (2)	C16—H16	0.9500
C8—C9	1.410 (2)	C17—C18	1.3900
C8—N1	1.412 (2)	C17—H17	0.9500
C9—O3	1.349 (2)	C18—C19	1.3900
C9—C10	1.388 (2)	C18—H18	0.9500
C10—C11	1.389 (3)	C19—C20	1.3900
C10—Cl4	1.7322 (18)	C19—H19	0.9500
C11—C12	1.382 (3)	C20—H20	0.9500
C6—C1—C2	117.62 (16)	C11—C12—Cl5	119.23 (14)
C6—C1—C7	127.06 (16)	C13—C12—Cl5	118.37 (14)
C2—C1—C7	115.31 (15)	C8—C13—C12	118.49 (16)
O1—C2—C3	117.23 (16)	C8—C13—H13	120.8
O1—C2—C1	122.78 (16)	C12—C13—H13	120.8
C3—C2—C1	119.98 (16)	C2—O1—H1O	104 (2)
C4—C3—C2	121.19 (16)	C9—O3—H3O	113 (2)
C4—C3—Cl1	119.95 (14)	C7—N1—C8	126.96 (16)
C2—C3—Cl1	118.85 (14)	C7—N1—H1N	117 (2)
C3—C4—C5	119.65 (17)	C8—N1—H1N	116 (2)
C3—C4—H4	120.2	C15—C14—H14A	109.5
C5—C4—H4	120.2	C15—C14—H14B	109.5
C4—C5—C6	120.81 (17)	H14A—C14—H14B	109.5
C4—C5—Cl2	117.80 (14)	C15—C14—H14C	109.5
C6—C5—Cl2	121.39 (14)	H14A—C14—H14C	109.5
C5—C6—C1	120.69 (16)	H14B—C14—H14C	109.5
C5—C6—Cl3	116.70 (14)	C16—C15—C20	120.0
C1—C6—Cl3	122.58 (14)	C16—C15—C14	119.2 (4)
O2—C7—N1	120.31 (16)	C20—C15—C14	120.8 (4)
O2—C7—C1	119.15 (16)	C17—C16—C15	120.0
N1—C7—C1	120.49 (16)	C17—C16—H16	120.0
C13—C8—C9	120.66 (16)	C15—C16—H16	120.0
C13—C8—N1	125.12 (16)	C16—C17—C18	120.0
C9—C8—N1	114.20 (16)	C16—C17—H17	120.0
O3—C9—C10	125.93 (16)	C18—C17—H17	120.0
O3—C9—C8	115.59 (15)	C19—C18—C17	120.0
C10—C9—C8	118.47 (16)	C19—C18—H18	120.0
C9—C10—C11	121.70 (17)	C17—C18—H18	120.0
C9—C10—Cl4	118.99 (14)	C20—C19—C18	120.0
C11—C10—Cl4	119.31 (14)	C20—C19—H19	120.0
C12—C11—C10	118.14 (17)	C18—C19—H19	120.0
C12—C11—H11	120.9	C19—C20—C15	120.0
C10—C11—H11	120.9	C19—C20—H20	120.0
C11—C12—C13	122.40 (17)	C15—C20—H20	120.0
C6—C1—C2—O1	−178.20 (16)	C13—C8—C9—C10	−4.2 (3)
C7—C1—C2—O1	2.8 (2)	N1—C8—C9—C10	177.61 (16)
C6—C1—C2—C3	2.8 (3)	O3—C9—C10—C11	−177.77 (17)
C7—C1—C2—C3	−176.21 (16)	C8—C9—C10—C11	3.1 (3)
O1—C2—C3—C4	178.79 (16)	O3—C9—C10—Cl4	2.8 (3)
C1—C2—C3—C4	−2.1 (3)	C8—C9—C10—Cl4	−176.29 (13)
O1—C2—C3—Cl1	−2.1 (2)	C9—C10—C11—C12	0.0 (3)
C1—C2—C3—Cl1	176.99 (13)	Cl4—C10—C11—C12	179.43 (14)
C2—C3—C4—C5	0.4 (3)	C10—C11—C12—C13	−2.2 (3)
Cl1—C3—C4—C5	−178.70 (14)	C10—C11—C12—Cl5	177.83 (14)
C3—C4—C5—C6	0.6 (3)	C9—C8—C13—C12	2.2 (3)
C3—C4—C5—Cl2	−179.97 (14)	N1—C8—C13—C12	−179.86 (16)
C4—C5—C6—C1	0.2 (3)	C11—C12—C13—C8	1.1 (3)
Cl2—C5—C6—C1	−179.27 (14)	Cl5—C12—C13—C8	−178.96 (13)
C4—C5—C6—Cl3	−178.02 (14)	O2—C7—N1—C8	−2.5 (3)
Cl2—C5—C6—Cl3	2.5 (2)	C1—C7—N1—C8	179.82 (15)
C2—C1—C6—C5	−1.8 (3)	C13—C8—N1—C7	13.9 (3)
C7—C1—C6—C5	177.04 (16)	C9—C8—N1—C7	−168.07 (17)
C2—C1—C6—Cl3	176.26 (13)	C20—C15—C16—C17	0.0
C7—C1—C6—Cl3	−4.9 (3)	C14—C15—C16—C17	179.7 (5)
C6—C1—C7—O2	168.38 (17)	C15—C16—C17—C18	0.0
C2—C1—C7—O2	−12.7 (2)	C16—C17—C18—C19	0.0
C6—C1—C7—N1	−13.9 (3)	C17—C18—C19—C20	0.0
C2—C1—C7—N1	164.96 (16)	C18—C19—C20—C15	0.0
C13—C8—C9—O3	176.55 (16)	C16—C15—C20—C19	0.0
N1—C8—C9—O3	−1.6 (2)	C14—C15—C20—C19	−179.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.77 (3)	1.70 (3)	2.4328 (19)	157 (3)
O1—H1O···Cl4^i	0.77 (3)	2.76 (3)	3.1736 (15)	116 (3)
O3—H3O···O1^ii	0.77 (3)	2.09 (3)	2.8247 (19)	162 (3)
O3—H3O···Cl4	0.77 (3)	2.65 (3)	3.0491 (14)	114 (3)
N1—H1N···O3	0.83 (3)	2.16 (3)	2.572 (2)	110 (2)
N1—H1N···Cl3	0.83 (3)	2.26 (3)	2.9608 (16)	143 (3)
C13—H13···O2	0.95	2.21	2.782 (2)	118
C4—H4···Cg1	0.95	2.75	3.551 (3)	143

Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z.

2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide chlorobenzene hemisolvate (IV)

Crystal data

C13H6Cl5NO3·0.5C6H5Cl	Z = 2
Mr = 457.71	F(000) = 458
Triclinic, P1	Dx = 1.785 Mg m^−3
a = 6.90927 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.69846 (10) Å	Cell parameters from 9026 reflections
c = 13.97198 (15) Å	θ = 2.7–30.5°
α = 86.5557 (5)°	µ = 0.95 mm^−1
β = 85.9678 (5)°	T = 100 K
γ = 65.8305 (5)°	Block, colorless
V = 851.56 (2) Å^3	0.32 × 0.22 × 0.13 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4583 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.039
Absorption correction: multi-scan SADABS, Bruker,2016	θmax = 30.5°, θmin = 2.3°
Tmin = 0.609, Tmax = 0.746	h = −9→9
28022 measured reflections	k = −13→13
5153 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0271P)^2 + 0.6071P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
5153 reflections	Δρmax = 0.47 e Å^−3
262 parameters	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5493 (2)	0.69889 (14)	0.63821 (9)	0.0124 (2)
C2	0.4238 (2)	0.85676 (15)	0.64551 (10)	0.0134 (2)
C3	0.3787 (2)	0.92250 (15)	0.73564 (10)	0.0146 (2)
C4	0.4472 (2)	0.83663 (15)	0.81823 (10)	0.0156 (3)
H4	0.4150	0.8830	0.8787	0.019*
C5	0.5641 (2)	0.68135 (15)	0.81268 (10)	0.0145 (2)
C6	0.6145 (2)	0.61251 (14)	0.72444 (10)	0.0133 (2)
C7	0.6001 (2)	0.64288 (15)	0.53757 (10)	0.0132 (2)
C8	0.8213 (2)	0.43816 (15)	0.42989 (9)	0.0127 (2)
C9	0.9564 (2)	0.28285 (15)	0.43559 (10)	0.0131 (2)
C10	1.0236 (2)	0.20416 (15)	0.35099 (10)	0.0136 (2)
C11	0.9688 (2)	0.27606 (15)	0.26157 (10)	0.0144 (2)
H11	1.0154	0.2212	0.2043	0.017*
C12	0.8442 (2)	0.43010 (15)	0.25871 (10)	0.0147 (2)
C13	0.7673 (2)	0.51275 (15)	0.34127 (10)	0.0140 (2)
H13	0.6796	0.6179	0.3372	0.017*
O1	0.34808 (17)	0.94815 (11)	0.56887 (8)	0.0177 (2)
H1O	0.387 (4)	0.887 (3)	0.5250 (19)	0.046 (7)*
O2	0.50180 (18)	0.72605 (12)	0.47023 (8)	0.0209 (2)
O3	1.00771 (18)	0.22409 (12)	0.52514 (7)	0.0178 (2)
H3O	1.092 (4)	0.140 (3)	0.5255 (18)	0.039 (6)*
N1	0.75516 (19)	0.50592 (13)	0.51990 (8)	0.0136 (2)
H1N	0.811 (3)	0.448 (2)	0.5671 (15)	0.025 (5)*
Cl1	0.23748 (6)	1.11544 (4)	0.74163 (3)	0.02096 (8)
Cl2	0.64438 (6)	0.57877 (4)	0.91872 (2)	0.02178 (8)
Cl3	0.75269 (6)	0.41765 (4)	0.72676 (2)	0.01719 (8)
Cl4	1.17772 (6)	0.01160 (4)	0.35736 (2)	0.01750 (8)
Cl5	0.77895 (6)	0.52445 (4)	0.14820 (2)	0.02178 (8)
C14	−0.0900 (4)	1.0315 (3)	0.9659 (2)	0.0260 (7)	0.5
C15	−0.0078 (4)	1.1389 (2)	0.97452 (18)	0.0239 (9)	0.5
H15	−0.0748	1.2367	0.9451	0.029*	0.5
C16	0.1722 (4)	1.1034 (3)	1.02614 (18)	0.0282 (7)	0.5
H16	0.2284	1.1768	1.0320	0.034*	0.5
C17	0.2702 (4)	0.9603 (3)	1.06916 (18)	0.0316 (11)	0.5
H17	0.3933	0.9360	1.1044	0.038*	0.5
C18	0.1880 (4)	0.8528 (2)	1.06057 (18)	0.0351 (9)	0.5
H18	0.2550	0.7551	1.0900	0.042*	0.5
C19	0.0079 (5)	0.8884 (3)	1.0089 (2)	0.0325 (11)	0.5
H19	−0.0482	0.8150	1.0031	0.039*	0.5
Cl6	−0.3135 (2)	1.07814 (16)	0.90176 (9)	0.0407 (3)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0122 (6)	0.0106 (5)	0.0131 (6)	−0.0035 (5)	−0.0008 (4)	−0.0007 (4)
C2	0.0135 (6)	0.0110 (6)	0.0143 (6)	−0.0038 (5)	−0.0006 (4)	0.0000 (4)
C3	0.0152 (6)	0.0100 (5)	0.0166 (6)	−0.0030 (5)	0.0002 (5)	−0.0021 (5)
C4	0.0174 (6)	0.0134 (6)	0.0150 (6)	−0.0051 (5)	0.0005 (5)	−0.0026 (5)
C5	0.0161 (6)	0.0138 (6)	0.0128 (6)	−0.0051 (5)	−0.0017 (5)	0.0004 (5)
C6	0.0134 (6)	0.0096 (5)	0.0152 (6)	−0.0029 (5)	−0.0012 (5)	0.0001 (4)
C7	0.0125 (6)	0.0120 (6)	0.0150 (6)	−0.0047 (5)	−0.0002 (4)	−0.0015 (4)
C8	0.0135 (6)	0.0111 (5)	0.0128 (6)	−0.0042 (5)	−0.0006 (4)	−0.0020 (4)
C9	0.0127 (6)	0.0114 (5)	0.0145 (6)	−0.0043 (5)	−0.0014 (4)	−0.0003 (4)
C10	0.0127 (6)	0.0102 (5)	0.0170 (6)	−0.0034 (5)	−0.0004 (5)	−0.0024 (5)
C11	0.0146 (6)	0.0150 (6)	0.0140 (6)	−0.0063 (5)	0.0004 (5)	−0.0025 (5)
C12	0.0164 (6)	0.0153 (6)	0.0125 (6)	−0.0066 (5)	−0.0010 (5)	0.0006 (5)
C13	0.0145 (6)	0.0110 (5)	0.0151 (6)	−0.0039 (5)	−0.0009 (5)	−0.0002 (4)
O1	0.0217 (5)	0.0101 (4)	0.0150 (5)	−0.0003 (4)	−0.0009 (4)	0.0006 (4)
O2	0.0242 (5)	0.0143 (5)	0.0148 (5)	0.0022 (4)	−0.0035 (4)	−0.0002 (4)
O3	0.0217 (5)	0.0103 (4)	0.0141 (5)	0.0013 (4)	−0.0029 (4)	0.0003 (4)
N1	0.0159 (5)	0.0094 (5)	0.0124 (5)	−0.0017 (4)	−0.0022 (4)	−0.0008 (4)
Cl1	0.02598 (18)	0.01007 (14)	0.02078 (16)	−0.00128 (12)	0.00118 (13)	−0.00281 (11)
Cl2	0.02931 (19)	0.01755 (16)	0.01339 (15)	−0.00417 (14)	−0.00417 (13)	0.00169 (12)
Cl3	0.02126 (16)	0.00969 (14)	0.01533 (15)	−0.00100 (12)	−0.00173 (11)	0.00117 (11)
Cl4	0.01932 (16)	0.01024 (14)	0.01891 (16)	−0.00172 (12)	−0.00009 (12)	−0.00291 (11)
Cl5	0.02782 (19)	0.02052 (16)	0.01319 (15)	−0.00618 (14)	−0.00201 (12)	0.00215 (12)
C14	0.0319 (17)	0.0290 (17)	0.0185 (14)	−0.0139 (14)	0.0076 (12)	−0.0094 (12)
C15	0.035 (2)	0.0153 (15)	0.0193 (17)	−0.0088 (15)	0.0071 (15)	−0.0042 (14)
C16	0.0372 (19)	0.0265 (16)	0.0223 (15)	−0.0139 (14)	0.0036 (13)	−0.0090 (12)
C17	0.036 (2)	0.033 (2)	0.0132 (19)	−0.0017 (18)	0.0022 (15)	−0.0026 (15)
C18	0.050 (2)	0.0225 (16)	0.0233 (16)	−0.0068 (16)	0.0082 (15)	0.0023 (13)
C19	0.047 (3)	0.025 (2)	0.028 (2)	−0.0186 (19)	0.0142 (18)	−0.0045 (17)
Cl6	0.0365 (6)	0.0541 (8)	0.0347 (7)	−0.0198 (6)	0.0001 (5)	−0.0163 (5)

Geometric parameters (Å, º)

C1—C6	1.4149 (18)	C11—C12	1.3853 (19)
C1—C2	1.4233 (18)	C11—H11	0.9500
C1—C7	1.5039 (18)	C12—C13	1.3897 (18)
C2—O1	1.3382 (16)	C12—Cl5	1.7365 (14)
C2—C3	1.4028 (18)	C13—H13	0.9500
C3—C4	1.3740 (19)	O1—H1O	0.83 (3)
C3—Cl1	1.7242 (13)	O3—H3O	0.78 (3)
C4—C5	1.3912 (18)	N1—H1N	0.84 (2)
C4—H4	0.9500	C14—C15	1.3900
C5—C6	1.3912 (18)	C14—C19	1.3900
C5—Cl2	1.7260 (14)	C14—Cl6	1.722 (2)
C6—Cl3	1.7331 (13)	C15—C16	1.3900
C7—O2	1.2439 (17)	C15—H15	0.9500
C7—N1	1.3453 (17)	C16—C17	1.3900
C8—C13	1.3900 (18)	C16—H16	0.9500
C8—C9	1.4111 (18)	C17—C18	1.3900
C8—N1	1.4124 (17)	C17—H17	0.9500
C9—O3	1.3517 (16)	C18—C19	1.3900
C9—C10	1.3916 (18)	C18—H18	0.9500
C10—C11	1.3914 (19)	C19—H19	0.9500
C10—Cl4	1.7305 (13)
C6—C1—C2	117.67 (12)	C12—C11—H11	121.0
C6—C1—C7	127.14 (12)	C10—C11—H11	121.0
C2—C1—C7	115.19 (11)	C11—C12—C13	122.51 (13)
O1—C2—C3	117.50 (12)	C11—C12—Cl5	119.17 (10)
O1—C2—C1	122.64 (12)	C13—C12—Cl5	118.32 (10)
C3—C2—C1	119.85 (12)	C12—C13—C8	118.55 (12)
C4—C3—C2	121.33 (12)	C12—C13—H13	120.7
C4—C3—Cl1	119.85 (10)	C8—C13—H13	120.7
C2—C3—Cl1	118.81 (10)	C2—O1—H1O	101.6 (18)
C3—C4—C5	119.53 (12)	C9—O3—H3O	112.9 (18)
C3—C4—H4	120.2	C7—N1—C8	127.01 (12)
C5—C4—H4	120.2	C7—N1—H1N	118.2 (14)
C4—C5—C6	120.75 (12)	C8—N1—H1N	114.3 (14)
C4—C5—Cl2	117.59 (10)	C15—C14—C19	120.0
C6—C5—Cl2	121.66 (10)	C15—C14—Cl6	119.20 (16)
C5—C6—C1	120.79 (12)	C19—C14—Cl6	120.80 (16)
C5—C6—Cl3	116.63 (10)	C16—C15—C14	120.0
C1—C6—Cl3	122.56 (10)	C16—C15—H15	120.0
O2—C7—N1	120.11 (13)	C14—C15—H15	120.0
O2—C7—C1	119.45 (12)	C15—C16—C17	120.0
N1—C7—C1	120.41 (12)	C15—C16—H16	120.0
C13—C8—C9	120.58 (12)	C17—C16—H16	120.0
C13—C8—N1	125.30 (12)	C18—C17—C16	120.0
C9—C8—N1	114.10 (12)	C18—C17—H17	120.0
O3—C9—C10	125.95 (12)	C16—C17—H17	120.0
O3—C9—C8	115.48 (12)	C17—C18—C19	120.0
C10—C9—C8	118.56 (12)	C17—C18—H18	120.0
C11—C10—C9	121.73 (12)	C19—C18—H18	120.0
C11—C10—Cl4	119.21 (10)	C18—C19—C14	120.0
C9—C10—Cl4	119.06 (10)	C18—C19—H19	120.0
C12—C11—C10	117.93 (12)	C14—C19—H19	120.0
C6—C1—C2—O1	−177.86 (13)	C13—C8—C9—C10	−3.9 (2)
C7—C1—C2—O1	2.85 (19)	N1—C8—C9—C10	177.42 (12)
C6—C1—C2—C3	3.4 (2)	O3—C9—C10—C11	−177.45 (13)
C7—C1—C2—C3	−175.92 (12)	C8—C9—C10—C11	3.0 (2)
O1—C2—C3—C4	178.92 (13)	O3—C9—C10—Cl4	3.0 (2)
C1—C2—C3—C4	−2.2 (2)	C8—C9—C10—Cl4	−176.60 (10)
O1—C2—C3—Cl1	−2.03 (18)	C9—C10—C11—C12	0.0 (2)
C1—C2—C3—Cl1	176.80 (10)	Cl4—C10—C11—C12	179.62 (10)
C2—C3—C4—C5	0.1 (2)	C10—C11—C12—C13	−2.3 (2)
Cl1—C3—C4—C5	−178.93 (11)	C10—C11—C12—Cl5	178.25 (10)
C3—C4—C5—C6	0.8 (2)	C11—C12—C13—C8	1.4 (2)
C3—C4—C5—Cl2	−179.50 (11)	Cl5—C12—C13—C8	−179.18 (10)
C4—C5—C6—C1	0.4 (2)	C9—C8—C13—C12	1.8 (2)
Cl2—C5—C6—C1	−179.24 (11)	N1—C8—C13—C12	−179.68 (13)
C4—C5—C6—Cl3	−177.82 (11)	O2—C7—N1—C8	−2.0 (2)
Cl2—C5—C6—Cl3	2.51 (17)	C1—C7—N1—C8	−179.87 (12)
C2—C1—C6—C5	−2.5 (2)	C13—C8—N1—C7	13.7 (2)
C7—C1—C6—C5	176.70 (13)	C9—C8—N1—C7	−167.68 (13)
C2—C1—C6—Cl3	175.65 (10)	C19—C14—C15—C16	0.0
C7—C1—C6—Cl3	−5.2 (2)	Cl6—C14—C15—C16	179.9 (2)
C6—C1—C7—O2	167.43 (14)	C14—C15—C16—C17	0.0
C2—C1—C7—O2	−13.36 (19)	C15—C16—C17—C18	0.0
C6—C1—C7—N1	−14.6 (2)	C16—C17—C18—C19	0.0
C2—C1—C7—N1	164.56 (13)	C17—C18—C19—C14	0.0
C13—C8—C9—O3	176.47 (12)	C15—C14—C19—C18	0.0
N1—C8—C9—O3	−2.20 (18)	Cl6—C14—C19—C18	−179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl4^i	0.83 (3)	2.78 (3)	3.1898 (11)	112 (2)
O1—H1O···O2	0.83 (3)	1.64 (3)	2.4382 (15)	160 (3)
O3—H3O···Cl4	0.78 (3)	2.64 (2)	3.0550 (11)	115 (2)
O3—H3O···O1^ii	0.78 (3)	2.07 (3)	2.8139 (14)	159 (2)
N1—H1N···Cl3	0.84 (2)	2.26 (2)	2.9656 (12)	141 (2)
N1—H1N···O3	0.84 (2)	2.13 (2)	2.5709 (15)	112 (2)
C13—H13···O2	0.95	2.22	2.7869 (17)	118
C4—H4···Cg1	0.95	2.76	3.5578 (18)	142

Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z.