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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, C
13H
6Cl
5NO
3·0.5C
6H
6, (I), oxyclozanide xylene hemisolvate, C
13H
6Cl
5NO
3·0.5C
8H
10, (II), and oxyclozanide toluene hemisolvate, C
13H
6Cl
5NO
3·0.5C
7H
8, (III), were structurally characterized. In this context, the crystal structure of oxyclozanide chlorobenzene hemisolvate, C
13H
6Cl
5NO
3·0.5C
6H
5Cl, (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
CCDC references: 1583525; 1583524; 1583523; 1583522
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
C13H6Cl5NO3·0.5C6H6 | 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) Å3 | 0.28 × 0.12 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H 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 reflections | Δρmax = 1.01 e Å−3 |
238 parameters | Δρmin = −0.45 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C16i | 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—C14i | 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) | C16i—C14—C15 | 120.2 (3) |
O2—C7—N1 | 120.6 (2) | C16i—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) | C14i—C16—C15 | 120.1 (3) |
O3—C9—C10 | 126.1 (2) | C14i—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) | C16i—C14—C15—C16 | 0.1 (5) |
C6—C1—C7—N1 | 22.1 (3) | C14—C15—C16—C14i | −0.1 (5) |
Symmetry code: (i) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
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···Cl4ii | 0.83 (4) | 2.80 (4) | 3.1912 (18) | 111 (3) |
O3—H3O···O1iii | 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···Cg1iv | 0.95 | 2.87 | 3.820 (3) | 177 |
C11—H11···Cg1v | 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)
top
Crystal data top
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) Å3 | 0.42 × 0.38 × 0.24 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H 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 reflections | Δρmax = 0.38 e Å−3 |
248 parameters | Δρmin = −0.39 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C17i | 1.387 (3) |
C8—N1 | 1.416 (2) | C16—H16 | 0.9500 |
C9—O3 | 1.357 (2) | C17—C16i | 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) | C17i—C16—C15 | 121.2 (2) |
O3—C9—C10 | 125.64 (17) | C17i—C16—H16 | 119.4 |
O3—C9—C8 | 115.85 (16) | C15—C16—H16 | 119.4 |
C10—C9—C8 | 118.50 (17) | C16i—C17—C15 | 121.0 (2) |
C11—C10—C9 | 122.09 (17) | C16i—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—C17i | −0.1 (3) |
C2—C1—C7—O2 | −10.6 (2) | C14—C15—C16—C17i | −179.22 (19) |
C6—C1—C7—N1 | −10.8 (3) | C16—C15—C17—C16i | 0.1 (3) |
C2—C1—C7—N1 | 168.40 (16) | C14—C15—C17—C16i | 179.22 (19) |
Symmetry code: (i) −x, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···Cl4ii | 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···O1iii | 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···Cg1i | 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)
top
Crystal data top
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) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H 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 reflections | Δρmax = 0.70 e Å−3 |
263 parameters | Δρmin = −0.36 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···Cl4i | 0.77 (3) | 2.76 (3) | 3.1736 (15) | 116 (3) |
O3—H3O···O1ii | 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)
top
Crystal data top
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) Å3 | 0.32 × 0.22 × 0.13 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H 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 reflections | Δρmax = 0.47 e Å−3 |
262 parameters | Δρmin = −0.40 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···Cl4i | 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···O1ii | 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. |
Details of π–π and Cl···Cl contacts (Å) observed in solvates (I)–(IV). topContacts | (I) | (II) | (III) | (IV) |
π–πv* | 3.8554 (14) | 3.6139 (13) | 3.6365 (12) | 3.6382 (9) |
π–πiv* | 3.6369 (14) | 4.2077 (13) | 3.9763 (12) | 3.9401 (9) |
Cl3···Cl1ii | 3.4113 (8) | 3.3727 (7) | 3.4304 (7) | 3.4407 (6) |
Cl2···Cl5vi | 3.5094 (9) | - | 3.4059 (6) | 3.3522 (4) |
Cl2···Cl2vii | 3.3107 (8) | 3.5964 (7) | 3.5884 (7) | 3.5938 (5) |
Cl2···Cl5iv/-/v/v | 3.6262 (10) | - | 3.6599 (8) | 3.6505 (6) |
Cl5···Cl5viii/-/-/- | 3.5779 (8) | - | - | - |
Cl4···O2ii | 3.2124 (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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