In the crystal of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, molecules are linked by C—H⋯N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. In methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate, molecules are linked by C—H⋯O hydrogen bonds and C—Cl⋯π interactions, forming layers parallel to (010). In methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate, molecules are linked by C—H⋯π and C—Cl⋯π interactions, forming chains parallel to [011].
Supporting information
CCDC references: 2327446; 2327447; 2327448
Methyl 4-{2,2-dichloro-1-[(
E)-phenyldiazenyl]ethenyl}benzoate (I)
top
Crystal data top
C16H12Cl2N2O2 | F(000) = 688 |
Mr = 335.18 | Dx = 1.510 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 15.47572 (16) Å | Cell parameters from 12282 reflections |
b = 4.16896 (4) Å | θ = 2.9–77.0° |
c = 23.2257 (2) Å | µ = 4.04 mm−1 |
β = 100.1964 (9)° | T = 100 K |
V = 1474.80 (2) Å3 | Prism, red |
Z = 4 | 0.22 × 0.13 × 0.11 mm |
Data collection top
XtaLAB Synergy, Dualflex, HyPix diffractometer | 2823 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.060 |
φ and ω scans | θmax = 77.8°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −19→19 |
Tmin = 0.404, Tmax = 0.600 | k = −5→5 |
23940 measured reflections | l = −29→28 |
3151 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0503P)2 + 1.3375P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3151 reflections | Δρmax = 0.46 e Å−3 |
200 parameters | Δρmin = −0.32 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 | |
Cl1 | 0.13479 (3) | 0.05540 (11) | 0.40331 (2) | 0.02247 (13) | |
Cl2 | 0.27874 (3) | 0.32473 (12) | 0.48326 (2) | 0.02639 (14) | |
O1 | 0.01936 (9) | 0.1723 (4) | 0.10978 (6) | 0.0285 (3) | |
O2 | 0.14455 (9) | −0.0786 (4) | 0.10100 (6) | 0.0268 (3) | |
N1 | 0.34295 (10) | 0.5658 (4) | 0.38299 (7) | 0.0216 (3) | |
N2 | 0.38242 (10) | 0.6368 (4) | 0.34161 (7) | 0.0211 (3) | |
C1 | 0.26399 (11) | 0.3911 (4) | 0.36605 (8) | 0.0207 (4) | |
C2 | 0.22931 (12) | 0.2761 (5) | 0.41127 (8) | 0.0214 (4) | |
C3 | 0.22169 (11) | 0.3354 (4) | 0.30397 (8) | 0.0197 (4) | |
C4 | 0.26794 (11) | 0.1764 (5) | 0.26603 (8) | 0.0210 (4) | |
H4 | 0.327649 | 0.119411 | 0.279023 | 0.025* | |
C5 | 0.22744 (12) | 0.1012 (5) | 0.20969 (8) | 0.0220 (4) | |
H5 | 0.259087 | −0.011130 | 0.184514 | 0.026* | |
C6 | 0.14025 (11) | 0.1895 (4) | 0.18962 (8) | 0.0203 (4) | |
C7 | 0.09485 (11) | 0.3596 (4) | 0.22649 (8) | 0.0215 (4) | |
H7 | 0.036219 | 0.427119 | 0.212652 | 0.026* | |
C8 | 0.13490 (12) | 0.4308 (5) | 0.28326 (8) | 0.0220 (4) | |
H8 | 0.103337 | 0.544786 | 0.308278 | 0.026* | |
C9 | 0.09401 (12) | 0.0996 (5) | 0.13000 (8) | 0.0215 (4) | |
C10 | 0.10264 (14) | −0.1883 (6) | 0.04358 (8) | 0.0293 (4) | |
H10A | 0.087522 | −0.003127 | 0.017776 | 0.044* | |
H10B | 0.049121 | −0.307201 | 0.046928 | 0.044* | |
H10C | 0.142947 | −0.328838 | 0.027228 | 0.044* | |
C11 | 0.46037 (11) | 0.8199 (4) | 0.36040 (8) | 0.0209 (4) | |
C12 | 0.51605 (12) | 0.8486 (5) | 0.31977 (8) | 0.0228 (4) | |
H12 | 0.500723 | 0.751252 | 0.282364 | 0.027* | |
C13 | 0.59408 (13) | 1.0194 (5) | 0.33381 (9) | 0.0255 (4) | |
H13 | 0.632190 | 1.038116 | 0.306098 | 0.031* | |
C14 | 0.61616 (12) | 1.1624 (5) | 0.38829 (9) | 0.0258 (4) | |
H14 | 0.670157 | 1.274595 | 0.398327 | 0.031* | |
C15 | 0.55900 (13) | 1.1414 (5) | 0.42850 (8) | 0.0264 (4) | |
H15 | 0.573440 | 1.245282 | 0.465361 | 0.032* | |
C16 | 0.48136 (12) | 0.9698 (5) | 0.41483 (8) | 0.0233 (4) | |
H16 | 0.442743 | 0.954405 | 0.442280 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0167 (2) | 0.0264 (2) | 0.0244 (2) | −0.00357 (16) | 0.00406 (15) | −0.00043 (16) |
Cl2 | 0.0217 (2) | 0.0355 (3) | 0.0213 (2) | −0.00499 (17) | 0.00171 (16) | −0.00103 (17) |
O1 | 0.0183 (6) | 0.0359 (8) | 0.0291 (7) | 0.0048 (6) | −0.0016 (5) | −0.0043 (6) |
O2 | 0.0193 (6) | 0.0382 (8) | 0.0220 (6) | 0.0047 (6) | 0.0016 (5) | −0.0046 (6) |
N1 | 0.0162 (7) | 0.0232 (8) | 0.0248 (7) | 0.0001 (6) | 0.0022 (6) | 0.0017 (6) |
N2 | 0.0153 (7) | 0.0216 (7) | 0.0260 (8) | 0.0007 (6) | 0.0025 (6) | 0.0023 (6) |
C1 | 0.0152 (8) | 0.0208 (8) | 0.0255 (9) | 0.0019 (7) | 0.0018 (7) | −0.0006 (7) |
C2 | 0.0163 (8) | 0.0233 (9) | 0.0241 (9) | 0.0006 (7) | 0.0023 (6) | −0.0014 (7) |
C3 | 0.0163 (8) | 0.0202 (8) | 0.0221 (9) | −0.0004 (7) | 0.0023 (6) | 0.0026 (7) |
C4 | 0.0142 (8) | 0.0244 (9) | 0.0241 (9) | 0.0035 (7) | 0.0029 (6) | 0.0038 (7) |
C5 | 0.0166 (8) | 0.0260 (9) | 0.0240 (9) | 0.0034 (7) | 0.0049 (7) | 0.0022 (7) |
C6 | 0.0159 (8) | 0.0220 (9) | 0.0224 (8) | −0.0002 (7) | 0.0021 (6) | 0.0025 (7) |
C7 | 0.0140 (8) | 0.0221 (9) | 0.0281 (9) | 0.0019 (7) | 0.0028 (7) | 0.0016 (7) |
C8 | 0.0153 (8) | 0.0248 (9) | 0.0261 (9) | 0.0004 (7) | 0.0044 (7) | −0.0011 (7) |
C9 | 0.0175 (8) | 0.0233 (9) | 0.0237 (9) | 0.0013 (7) | 0.0038 (7) | 0.0019 (7) |
C10 | 0.0264 (10) | 0.0391 (11) | 0.0214 (9) | 0.0002 (8) | 0.0018 (7) | −0.0053 (8) |
C11 | 0.0140 (8) | 0.0219 (9) | 0.0259 (9) | 0.0017 (7) | 0.0011 (6) | 0.0034 (7) |
C12 | 0.0205 (9) | 0.0238 (9) | 0.0246 (9) | 0.0002 (7) | 0.0053 (7) | 0.0005 (7) |
C13 | 0.0195 (9) | 0.0274 (10) | 0.0306 (10) | 0.0009 (8) | 0.0077 (7) | 0.0020 (8) |
C14 | 0.0155 (8) | 0.0291 (10) | 0.0319 (10) | −0.0030 (7) | 0.0014 (7) | 0.0046 (8) |
C15 | 0.0233 (9) | 0.0305 (10) | 0.0241 (9) | −0.0045 (8) | 0.0004 (7) | 0.0017 (8) |
C16 | 0.0189 (9) | 0.0282 (9) | 0.0227 (9) | −0.0010 (7) | 0.0037 (7) | 0.0035 (7) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.7102 (19) | C7—C8 | 1.386 (3) |
Cl2—C2 | 1.7231 (18) | C7—H7 | 0.9500 |
O1—C9 | 1.206 (2) | C8—H8 | 0.9500 |
O2—C9 | 1.343 (2) | C10—H10A | 0.9800 |
O2—C10 | 1.450 (2) | C10—H10B | 0.9800 |
N1—N2 | 1.262 (2) | C10—H10C | 0.9800 |
N1—C1 | 1.417 (2) | C11—C12 | 1.391 (3) |
N2—C11 | 1.429 (2) | C11—C16 | 1.396 (3) |
C1—C2 | 1.349 (3) | C12—C13 | 1.390 (3) |
C1—C3 | 1.492 (2) | C12—H12 | 0.9500 |
C3—C4 | 1.397 (3) | C13—C14 | 1.386 (3) |
C3—C8 | 1.402 (2) | C13—H13 | 0.9500 |
C4—C5 | 1.383 (3) | C14—C15 | 1.398 (3) |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.397 (2) | C15—C16 | 1.386 (3) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.394 (3) | C16—H16 | 0.9500 |
C6—C9 | 1.490 (3) | | |
| | | |
C9—O2—C10 | 115.49 (15) | O1—C9—O2 | 123.12 (17) |
N2—N1—C1 | 114.77 (15) | O1—C9—C6 | 124.62 (17) |
N1—N2—C11 | 112.90 (15) | O2—C9—C6 | 112.26 (15) |
C2—C1—N1 | 114.12 (16) | O2—C10—H10A | 109.5 |
C2—C1—C3 | 121.99 (16) | O2—C10—H10B | 109.5 |
N1—C1—C3 | 123.89 (16) | H10A—C10—H10B | 109.5 |
C1—C2—Cl1 | 123.88 (14) | O2—C10—H10C | 109.5 |
C1—C2—Cl2 | 122.96 (14) | H10A—C10—H10C | 109.5 |
Cl1—C2—Cl2 | 113.11 (11) | H10B—C10—H10C | 109.5 |
C4—C3—C8 | 119.01 (16) | C12—C11—C16 | 120.20 (17) |
C4—C3—C1 | 119.81 (16) | C12—C11—N2 | 115.44 (16) |
C8—C3—C1 | 121.15 (16) | C16—C11—N2 | 124.36 (16) |
C5—C4—C3 | 120.48 (16) | C13—C12—C11 | 120.10 (18) |
C5—C4—H4 | 119.8 | C13—C12—H12 | 119.9 |
C3—C4—H4 | 119.8 | C11—C12—H12 | 119.9 |
C4—C5—C6 | 120.35 (17) | C14—C13—C12 | 119.88 (18) |
C4—C5—H5 | 119.8 | C14—C13—H13 | 120.1 |
C6—C5—H5 | 119.8 | C12—C13—H13 | 120.1 |
C7—C6—C5 | 119.42 (17) | C13—C14—C15 | 120.01 (18) |
C7—C6—C9 | 119.19 (16) | C13—C14—H14 | 120.0 |
C5—C6—C9 | 121.38 (17) | C15—C14—H14 | 120.0 |
C8—C7—C6 | 120.28 (16) | C16—C15—C14 | 120.30 (18) |
C8—C7—H7 | 119.9 | C16—C15—H15 | 119.8 |
C6—C7—H7 | 119.9 | C14—C15—H15 | 119.8 |
C7—C8—C3 | 120.38 (17) | C15—C16—C11 | 119.46 (17) |
C7—C8—H8 | 119.8 | C15—C16—H16 | 120.3 |
C3—C8—H8 | 119.8 | C11—C16—H16 | 120.3 |
| | | |
C1—N1—N2—C11 | 178.44 (15) | C4—C3—C8—C7 | 1.9 (3) |
N2—N1—C1—C2 | 170.71 (16) | C1—C3—C8—C7 | −176.03 (17) |
N2—N1—C1—C3 | −9.2 (3) | C10—O2—C9—O1 | −1.8 (3) |
N1—C1—C2—Cl1 | −179.62 (13) | C10—O2—C9—C6 | 177.22 (16) |
C3—C1—C2—Cl1 | 0.3 (3) | C7—C6—C9—O1 | 2.5 (3) |
N1—C1—C2—Cl2 | −2.2 (2) | C5—C6—C9—O1 | −178.85 (19) |
C3—C1—C2—Cl2 | 177.66 (14) | C7—C6—C9—O2 | −176.46 (17) |
C2—C1—C3—C4 | −120.9 (2) | C5—C6—C9—O2 | 2.2 (3) |
N1—C1—C3—C4 | 59.0 (3) | N1—N2—C11—C12 | 167.20 (16) |
C2—C1—C3—C8 | 57.0 (3) | N1—N2—C11—C16 | −14.1 (3) |
N1—C1—C3—C8 | −123.1 (2) | C16—C11—C12—C13 | 1.8 (3) |
C8—C3—C4—C5 | −2.9 (3) | N2—C11—C12—C13 | −179.43 (17) |
C1—C3—C4—C5 | 175.04 (17) | C11—C12—C13—C14 | −0.3 (3) |
C3—C4—C5—C6 | 1.4 (3) | C12—C13—C14—C15 | −1.6 (3) |
C4—C5—C6—C7 | 1.2 (3) | C13—C14—C15—C16 | 2.0 (3) |
C4—C5—C6—C9 | −177.42 (17) | C14—C15—C16—C11 | −0.5 (3) |
C5—C6—C7—C8 | −2.2 (3) | C12—C11—C16—C15 | −1.4 (3) |
C9—C6—C7—C8 | 176.44 (17) | N2—C11—C16—C15 | 179.91 (18) |
C6—C7—C8—C3 | 0.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N2i | 0.95 | 2.54 | 3.191 (3) | 126 |
C5—H5···O2 | 0.95 | 2.40 | 2.726 (2) | 100 |
Symmetry code: (i) x, y−1, z. |
Methyl 4-{2,2-dichloro-1-[(
E)-(4-methylphenyl)diazenyl]ethenyl}benzoate (II)
top
Crystal data top
C17H14Cl2N2O2 | F(000) = 720 |
Mr = 349.20 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 15.6177 (2) Å | Cell parameters from 12932 reflections |
b = 8.47502 (11) Å | θ = 3.0–77.0° |
c = 13.10365 (17) Å | µ = 3.67 mm−1 |
β = 109.6555 (15)° | T = 100 K |
V = 1633.34 (4) Å3 | Prism, red |
Z = 4 | 0.26 × 0.19 × 0.17 mm |
Data collection top
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3197 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.054 |
φ and ω scans | θmax = 78.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −15→19 |
Tmin = 0.307, Tmax = 0.530 | k = −10→10 |
28857 measured reflections | l = −16→16 |
3469 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0579P)2 + 0.7484P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.13 | Δρmax = 0.30 e Å−3 |
3469 reflections | Δρmin = −0.48 e Å−3 |
211 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0012 (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 | |
Cl1 | 0.98647 (3) | 0.77109 (5) | 0.27683 (3) | 0.02442 (14) | |
Cl2 | 0.94376 (3) | 0.63249 (5) | 0.06421 (3) | 0.02432 (14) | |
O1 | 0.69644 (8) | 0.59702 (16) | 0.60175 (10) | 0.0264 (3) | |
O2 | 0.81960 (8) | 0.44134 (15) | 0.66154 (9) | 0.0245 (3) | |
N1 | 0.78451 (9) | 0.49845 (18) | 0.10125 (11) | 0.0209 (3) | |
N2 | 0.71406 (9) | 0.44374 (18) | 0.11566 (11) | 0.0219 (3) | |
C1 | 0.84094 (11) | 0.5841 (2) | 0.19136 (13) | 0.0199 (3) | |
C2 | 0.91421 (11) | 0.6533 (2) | 0.17879 (13) | 0.0210 (3) | |
C3 | 0.82373 (11) | 0.5849 (2) | 0.29668 (13) | 0.0196 (3) | |
C4 | 0.74921 (11) | 0.6634 (2) | 0.30912 (13) | 0.0216 (3) | |
H4 | 0.710519 | 0.725291 | 0.251576 | 0.026* | |
C5 | 0.73197 (11) | 0.6504 (2) | 0.40622 (14) | 0.0220 (3) | |
H5 | 0.682177 | 0.705534 | 0.415595 | 0.026* | |
C6 | 0.78742 (11) | 0.5568 (2) | 0.48977 (13) | 0.0195 (3) | |
C7 | 0.86273 (11) | 0.4802 (2) | 0.47817 (13) | 0.0208 (3) | |
H7 | 0.901389 | 0.418074 | 0.535632 | 0.025* | |
C8 | 0.88054 (11) | 0.4957 (2) | 0.38166 (13) | 0.0207 (3) | |
H8 | 0.932079 | 0.444724 | 0.373610 | 0.025* | |
C9 | 0.76178 (11) | 0.5361 (2) | 0.58862 (13) | 0.0204 (3) | |
C10 | 0.79809 (13) | 0.4119 (2) | 0.75872 (14) | 0.0275 (4) | |
H10A | 0.839975 | 0.332619 | 0.802976 | 0.041* | |
H10B | 0.735518 | 0.373025 | 0.739045 | 0.041* | |
H10C | 0.804167 | 0.510044 | 0.800106 | 0.041* | |
C11 | 0.65821 (11) | 0.3536 (2) | 0.02710 (13) | 0.0215 (3) | |
C12 | 0.57409 (12) | 0.3086 (3) | 0.03265 (15) | 0.0296 (4) | |
H12 | 0.556200 | 0.343233 | 0.091445 | 0.036* | |
C13 | 0.51651 (13) | 0.2138 (3) | −0.04704 (16) | 0.0314 (4) | |
H13 | 0.458899 | 0.185192 | −0.043069 | 0.038* | |
C14 | 0.54206 (12) | 0.1597 (2) | −0.13325 (14) | 0.0249 (4) | |
C15 | 0.62625 (12) | 0.2063 (2) | −0.13829 (14) | 0.0233 (4) | |
H15 | 0.644226 | 0.171215 | −0.196914 | 0.028* | |
C16 | 0.68413 (11) | 0.3026 (2) | −0.05973 (13) | 0.0217 (3) | |
H16 | 0.741000 | 0.333796 | −0.064785 | 0.026* | |
C17 | 0.48059 (13) | 0.0527 (3) | −0.21805 (16) | 0.0337 (4) | |
H17A | 0.516980 | −0.029287 | −0.236871 | 0.050* | |
H17B | 0.448259 | 0.114318 | −0.282843 | 0.050* | |
H17C | 0.436482 | 0.003205 | −0.189705 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0228 (2) | 0.0257 (2) | 0.0259 (2) | −0.00466 (15) | 0.00965 (16) | −0.00107 (15) |
Cl2 | 0.0258 (2) | 0.0280 (2) | 0.0246 (2) | 0.00138 (15) | 0.01564 (16) | 0.00240 (15) |
O1 | 0.0245 (6) | 0.0358 (7) | 0.0220 (6) | 0.0048 (5) | 0.0119 (5) | −0.0007 (5) |
O2 | 0.0266 (6) | 0.0303 (7) | 0.0204 (6) | 0.0048 (5) | 0.0131 (5) | 0.0057 (5) |
N1 | 0.0212 (6) | 0.0230 (7) | 0.0204 (6) | −0.0009 (5) | 0.0094 (5) | 0.0002 (5) |
N2 | 0.0223 (7) | 0.0248 (7) | 0.0202 (7) | −0.0011 (6) | 0.0093 (5) | −0.0005 (6) |
C1 | 0.0209 (7) | 0.0203 (8) | 0.0200 (8) | 0.0022 (6) | 0.0087 (6) | 0.0015 (6) |
C2 | 0.0219 (8) | 0.0212 (8) | 0.0214 (8) | 0.0017 (6) | 0.0092 (6) | 0.0008 (6) |
C3 | 0.0206 (7) | 0.0205 (8) | 0.0197 (8) | −0.0039 (6) | 0.0095 (6) | −0.0019 (6) |
C4 | 0.0213 (8) | 0.0228 (8) | 0.0209 (8) | 0.0013 (6) | 0.0075 (6) | 0.0026 (6) |
C5 | 0.0209 (8) | 0.0231 (8) | 0.0246 (8) | 0.0008 (6) | 0.0112 (6) | −0.0010 (6) |
C6 | 0.0206 (7) | 0.0205 (8) | 0.0188 (7) | −0.0028 (6) | 0.0086 (6) | −0.0019 (6) |
C7 | 0.0199 (7) | 0.0228 (8) | 0.0206 (7) | −0.0001 (6) | 0.0079 (6) | −0.0009 (6) |
C8 | 0.0200 (7) | 0.0221 (8) | 0.0221 (8) | −0.0009 (6) | 0.0099 (6) | −0.0030 (6) |
C9 | 0.0199 (7) | 0.0223 (8) | 0.0201 (7) | −0.0026 (6) | 0.0081 (6) | −0.0032 (6) |
C10 | 0.0323 (9) | 0.0340 (10) | 0.0210 (8) | 0.0027 (8) | 0.0153 (7) | 0.0043 (7) |
C11 | 0.0227 (8) | 0.0230 (8) | 0.0196 (8) | −0.0004 (6) | 0.0081 (6) | 0.0001 (6) |
C12 | 0.0265 (9) | 0.0407 (11) | 0.0261 (9) | −0.0058 (8) | 0.0146 (7) | −0.0065 (8) |
C13 | 0.0238 (8) | 0.0438 (12) | 0.0302 (9) | −0.0093 (8) | 0.0138 (7) | −0.0067 (8) |
C14 | 0.0260 (8) | 0.0256 (9) | 0.0226 (8) | −0.0018 (7) | 0.0076 (7) | −0.0007 (7) |
C15 | 0.0273 (8) | 0.0244 (9) | 0.0206 (8) | 0.0019 (7) | 0.0112 (7) | 0.0008 (7) |
C16 | 0.0222 (8) | 0.0236 (8) | 0.0214 (8) | 0.0002 (6) | 0.0101 (6) | 0.0015 (7) |
C17 | 0.0319 (9) | 0.0391 (11) | 0.0300 (9) | −0.0093 (8) | 0.0105 (8) | −0.0090 (8) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.7159 (17) | C7—H7 | 0.9500 |
Cl2—C2 | 1.7217 (16) | C8—H8 | 0.9500 |
O1—C9 | 1.207 (2) | C10—H10A | 0.9800 |
O2—C9 | 1.339 (2) | C10—H10B | 0.9800 |
O2—C10 | 1.4438 (19) | C10—H10C | 0.9800 |
N1—N2 | 1.265 (2) | C11—C12 | 1.393 (2) |
N1—C1 | 1.414 (2) | C11—C16 | 1.398 (2) |
N2—C11 | 1.418 (2) | C12—C13 | 1.383 (3) |
C1—C2 | 1.345 (2) | C12—H12 | 0.9500 |
C1—C3 | 1.492 (2) | C13—C14 | 1.396 (3) |
C3—C8 | 1.391 (2) | C13—H13 | 0.9500 |
C3—C4 | 1.397 (2) | C14—C15 | 1.396 (2) |
C4—C5 | 1.391 (2) | C14—C17 | 1.504 (2) |
C4—H4 | 0.9500 | C15—C16 | 1.385 (2) |
C5—C6 | 1.393 (2) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—C7 | 1.396 (2) | C17—H17A | 0.9800 |
C6—C9 | 1.489 (2) | C17—H17B | 0.9800 |
C7—C8 | 1.389 (2) | C17—H17C | 0.9800 |
| | | |
C9—O2—C10 | 115.59 (13) | O2—C10—H10A | 109.5 |
N2—N1—C1 | 113.13 (13) | O2—C10—H10B | 109.5 |
N1—N2—C11 | 113.70 (13) | H10A—C10—H10B | 109.5 |
C2—C1—N1 | 116.03 (14) | O2—C10—H10C | 109.5 |
C2—C1—C3 | 122.48 (15) | H10A—C10—H10C | 109.5 |
N1—C1—C3 | 121.28 (14) | H10B—C10—H10C | 109.5 |
C1—C2—Cl1 | 122.31 (13) | C12—C11—C16 | 119.63 (16) |
C1—C2—Cl2 | 123.43 (13) | C12—C11—N2 | 115.85 (15) |
Cl1—C2—Cl2 | 114.26 (9) | C16—C11—N2 | 124.45 (15) |
C8—C3—C4 | 119.85 (15) | C13—C12—C11 | 120.30 (16) |
C8—C3—C1 | 118.23 (14) | C13—C12—H12 | 119.8 |
C4—C3—C1 | 121.77 (15) | C11—C12—H12 | 119.8 |
C5—C4—C3 | 119.63 (15) | C12—C13—C14 | 120.76 (16) |
C5—C4—H4 | 120.2 | C12—C13—H13 | 119.6 |
C3—C4—H4 | 120.2 | C14—C13—H13 | 119.6 |
C4—C5—C6 | 120.25 (15) | C15—C14—C13 | 118.40 (16) |
C4—C5—H5 | 119.9 | C15—C14—C17 | 120.88 (16) |
C6—C5—H5 | 119.9 | C13—C14—C17 | 120.72 (16) |
C5—C6—C7 | 120.22 (14) | C16—C15—C14 | 121.44 (15) |
C5—C6—C9 | 118.22 (14) | C16—C15—H15 | 119.3 |
C7—C6—C9 | 121.52 (15) | C14—C15—H15 | 119.3 |
C8—C7—C6 | 119.28 (15) | C15—C16—C11 | 119.45 (15) |
C8—C7—H7 | 120.4 | C15—C16—H16 | 120.3 |
C6—C7—H7 | 120.4 | C11—C16—H16 | 120.3 |
C7—C8—C3 | 120.73 (15) | C14—C17—H17A | 109.5 |
C7—C8—H8 | 119.6 | C14—C17—H17B | 109.5 |
C3—C8—H8 | 119.6 | H17A—C17—H17B | 109.5 |
O1—C9—O2 | 123.68 (15) | C14—C17—H17C | 109.5 |
O1—C9—C6 | 124.15 (15) | H17A—C17—H17C | 109.5 |
O2—C9—C6 | 112.17 (13) | H17B—C17—H17C | 109.5 |
| | | |
C1—N1—N2—C11 | −178.24 (14) | C1—C3—C8—C7 | −173.98 (15) |
N2—N1—C1—C2 | −176.18 (15) | C10—O2—C9—O1 | 1.4 (2) |
N2—N1—C1—C3 | 8.9 (2) | C10—O2—C9—C6 | −178.45 (14) |
N1—C1—C2—Cl1 | 176.23 (12) | C5—C6—C9—O1 | −1.0 (3) |
C3—C1—C2—Cl1 | −8.9 (2) | C7—C6—C9—O1 | −178.47 (17) |
N1—C1—C2—Cl2 | −3.7 (2) | C5—C6—C9—O2 | 178.82 (14) |
C3—C1—C2—Cl2 | 171.16 (13) | C7—C6—C9—O2 | 1.4 (2) |
C2—C1—C3—C8 | −69.6 (2) | N1—N2—C11—C12 | −171.71 (16) |
N1—C1—C3—C8 | 104.94 (19) | N1—N2—C11—C16 | 11.5 (2) |
C2—C1—C3—C4 | 114.81 (19) | C16—C11—C12—C13 | 0.1 (3) |
N1—C1—C3—C4 | −70.6 (2) | N2—C11—C12—C13 | −176.77 (18) |
C8—C3—C4—C5 | −0.6 (2) | C11—C12—C13—C14 | 1.0 (3) |
C1—C3—C4—C5 | 174.91 (16) | C12—C13—C14—C15 | −1.3 (3) |
C3—C4—C5—C6 | −1.5 (3) | C12—C13—C14—C17 | 178.15 (19) |
C4—C5—C6—C7 | 2.4 (3) | C13—C14—C15—C16 | 0.6 (3) |
C4—C5—C6—C9 | −175.06 (15) | C17—C14—C15—C16 | −178.87 (17) |
C5—C6—C7—C8 | −1.3 (2) | C14—C15—C16—C11 | 0.5 (3) |
C9—C6—C7—C8 | 176.06 (15) | C12—C11—C16—C15 | −0.9 (3) |
C6—C7—C8—C3 | −0.7 (3) | N2—C11—C16—C15 | 175.78 (16) |
C4—C3—C8—C7 | 1.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.95 | 2.43 | 3.268 (2) | 148 |
C13—H13···O1ii | 0.95 | 2.40 | 3.309 (3) | 159 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2. |
Methyl
4-{2,2-dichloro-1-[(
E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate (III)
top
Crystal data top
C18H16Cl2N2O2 | Z = 2 |
Mr = 363.23 | F(000) = 376 |
Triclinic, P1 | Dx = 1.412 Mg m−3 |
a = 8.22057 (10) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.53211 (9) Å | Cell parameters from 14210 reflections |
c = 13.08729 (14) Å | θ = 3.6–77.0° |
α = 103.9484 (9)° | µ = 3.53 mm−1 |
β = 101.9047 (10)° | T = 100 K |
γ = 98.0600 (9)° | Prism, red |
V = 854.09 (2) Å3 | 0.20 × 0.15 × 0.09 mm |
Data collection top
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3340 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.063 |
φ and ω scans | θmax = 77.8°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −10→10 |
Tmin = 0.349, Tmax = 0.700 | k = −8→10 |
29808 measured reflections | l = −16→16 |
3632 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2636P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3632 reflections | Δρmax = 0.31 e Å−3 |
220 parameters | Δρmin = −0.46 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 | |
Cl1 | 0.07283 (5) | −0.14861 (4) | 0.77715 (3) | 0.02444 (11) | |
Cl2 | 0.13915 (5) | −0.31047 (4) | 0.57534 (3) | 0.02637 (12) | |
O1 | 0.30977 (14) | 0.68544 (14) | 1.04185 (9) | 0.0315 (3) | |
O2 | 0.04043 (13) | 0.67433 (12) | 0.95696 (8) | 0.0208 (2) | |
N1 | 0.21612 (15) | 0.01951 (15) | 0.54534 (10) | 0.0198 (2) | |
N2 | 0.26094 (15) | 0.16265 (15) | 0.53648 (10) | 0.0208 (3) | |
C1 | 0.17177 (17) | 0.02110 (17) | 0.64440 (11) | 0.0189 (3) | |
C2 | 0.13347 (18) | −0.12681 (18) | 0.66254 (11) | 0.0206 (3) | |
C3 | 0.17331 (18) | 0.17742 (17) | 0.72590 (11) | 0.0185 (3) | |
C4 | 0.05481 (18) | 0.27494 (17) | 0.70373 (11) | 0.0203 (3) | |
H4 | −0.026457 | 0.242988 | 0.635554 | 0.024* | |
C5 | 0.05592 (18) | 0.41897 (17) | 0.78162 (12) | 0.0203 (3) | |
H5 | −0.026072 | 0.484181 | 0.767260 | 0.024* | |
C6 | 0.17767 (17) | 0.46736 (17) | 0.88079 (11) | 0.0188 (3) | |
C7 | 0.29835 (18) | 0.37242 (17) | 0.90121 (11) | 0.0202 (3) | |
H7 | 0.382930 | 0.406872 | 0.968032 | 0.024* | |
C8 | 0.29570 (18) | 0.22742 (17) | 0.82428 (12) | 0.0202 (3) | |
H8 | 0.377651 | 0.162276 | 0.838900 | 0.024* | |
C9 | 0.18624 (18) | 0.61892 (17) | 0.96841 (12) | 0.0209 (3) | |
C10 | 0.0464 (2) | 0.82424 (18) | 1.03931 (12) | 0.0244 (3) | |
H10A | −0.063270 | 0.858160 | 1.025427 | 0.037* | |
H10B | 0.135720 | 0.911518 | 1.037093 | 0.037* | |
H10C | 0.070772 | 0.804528 | 1.111150 | 0.037* | |
C11 | 0.31099 (18) | 0.16259 (18) | 0.43840 (11) | 0.0207 (3) | |
C12 | 0.33518 (19) | 0.31514 (18) | 0.41637 (12) | 0.0232 (3) | |
H12 | 0.318547 | 0.409355 | 0.466000 | 0.028* | |
C13 | 0.38330 (18) | 0.3316 (2) | 0.32285 (13) | 0.0249 (3) | |
C14 | 0.40929 (18) | 0.1914 (2) | 0.25099 (12) | 0.0258 (3) | |
C15 | 0.38626 (19) | 0.0399 (2) | 0.27461 (12) | 0.0260 (3) | |
H15 | 0.403729 | −0.054527 | 0.225581 | 0.031* | |
C16 | 0.33864 (19) | 0.02371 (19) | 0.36759 (12) | 0.0231 (3) | |
H16 | 0.325038 | −0.079976 | 0.382923 | 0.028* | |
C17 | 0.4088 (2) | 0.4974 (2) | 0.30023 (15) | 0.0333 (4) | |
H17A | 0.376239 | 0.578206 | 0.355458 | 0.050* | |
H17B | 0.338263 | 0.488834 | 0.228149 | 0.050* | |
H17C | 0.528407 | 0.532926 | 0.302386 | 0.050* | |
C18 | 0.4627 (2) | 0.2029 (3) | 0.14898 (14) | 0.0363 (4) | |
H18A | 0.377011 | 0.242730 | 0.103353 | 0.055* | |
H18B | 0.473909 | 0.093688 | 0.108817 | 0.055* | |
H18C | 0.571996 | 0.279612 | 0.168542 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0346 (2) | 0.02094 (19) | 0.02065 (18) | 0.00298 (14) | 0.01118 (14) | 0.00900 (14) |
Cl2 | 0.0402 (2) | 0.01643 (18) | 0.02316 (19) | 0.00645 (14) | 0.01064 (15) | 0.00402 (13) |
O1 | 0.0278 (6) | 0.0277 (6) | 0.0306 (6) | 0.0074 (5) | 0.0038 (5) | −0.0053 (5) |
O2 | 0.0259 (5) | 0.0182 (5) | 0.0211 (5) | 0.0070 (4) | 0.0100 (4) | 0.0059 (4) |
N1 | 0.0231 (6) | 0.0194 (6) | 0.0185 (6) | 0.0034 (5) | 0.0077 (5) | 0.0066 (5) |
N2 | 0.0240 (6) | 0.0199 (6) | 0.0198 (6) | 0.0025 (5) | 0.0092 (5) | 0.0060 (5) |
C1 | 0.0214 (6) | 0.0188 (7) | 0.0171 (6) | 0.0034 (5) | 0.0071 (5) | 0.0044 (5) |
C2 | 0.0251 (7) | 0.0191 (7) | 0.0180 (6) | 0.0041 (5) | 0.0070 (5) | 0.0049 (5) |
C3 | 0.0234 (7) | 0.0164 (6) | 0.0187 (6) | 0.0017 (5) | 0.0108 (5) | 0.0069 (5) |
C4 | 0.0247 (7) | 0.0203 (7) | 0.0174 (6) | 0.0040 (5) | 0.0071 (5) | 0.0070 (5) |
C5 | 0.0242 (7) | 0.0190 (7) | 0.0216 (7) | 0.0063 (5) | 0.0097 (6) | 0.0088 (5) |
C6 | 0.0234 (7) | 0.0170 (6) | 0.0189 (7) | 0.0029 (5) | 0.0103 (5) | 0.0067 (5) |
C7 | 0.0216 (7) | 0.0204 (7) | 0.0186 (6) | 0.0020 (5) | 0.0063 (5) | 0.0056 (5) |
C8 | 0.0227 (7) | 0.0191 (7) | 0.0218 (7) | 0.0060 (5) | 0.0093 (5) | 0.0070 (5) |
C9 | 0.0248 (7) | 0.0194 (7) | 0.0219 (7) | 0.0050 (5) | 0.0105 (6) | 0.0079 (6) |
C10 | 0.0337 (8) | 0.0179 (7) | 0.0262 (7) | 0.0080 (6) | 0.0152 (6) | 0.0066 (6) |
C11 | 0.0212 (7) | 0.0231 (7) | 0.0190 (7) | 0.0025 (5) | 0.0085 (5) | 0.0063 (6) |
C12 | 0.0247 (7) | 0.0226 (7) | 0.0230 (7) | 0.0022 (6) | 0.0084 (6) | 0.0069 (6) |
C13 | 0.0214 (7) | 0.0299 (8) | 0.0252 (7) | 0.0006 (6) | 0.0064 (6) | 0.0129 (6) |
C14 | 0.0206 (7) | 0.0376 (9) | 0.0214 (7) | 0.0024 (6) | 0.0085 (6) | 0.0114 (6) |
C15 | 0.0245 (7) | 0.0313 (8) | 0.0235 (7) | 0.0052 (6) | 0.0119 (6) | 0.0049 (6) |
C16 | 0.0247 (7) | 0.0226 (7) | 0.0244 (7) | 0.0042 (6) | 0.0108 (6) | 0.0072 (6) |
C17 | 0.0366 (9) | 0.0343 (9) | 0.0335 (9) | 0.0011 (7) | 0.0109 (7) | 0.0192 (7) |
C18 | 0.0376 (9) | 0.0506 (11) | 0.0260 (8) | 0.0047 (8) | 0.0162 (7) | 0.0157 (8) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.7176 (14) | C10—H10A | 0.9800 |
Cl2—C2 | 1.7148 (14) | C10—H10B | 0.9800 |
O1—C9 | 1.2041 (19) | C10—H10C | 0.9800 |
O2—C9 | 1.3422 (17) | C11—C16 | 1.396 (2) |
O2—C10 | 1.4478 (17) | C11—C12 | 1.396 (2) |
N1—N2 | 1.2651 (17) | C12—C13 | 1.393 (2) |
N1—C1 | 1.4148 (17) | C12—H12 | 0.9500 |
N2—C11 | 1.4263 (17) | C13—C14 | 1.404 (2) |
C1—C2 | 1.346 (2) | C13—C17 | 1.509 (2) |
C1—C3 | 1.4901 (19) | C14—C15 | 1.397 (2) |
C3—C8 | 1.390 (2) | C14—C18 | 1.509 (2) |
C3—C4 | 1.397 (2) | C15—C16 | 1.384 (2) |
C4—C5 | 1.392 (2) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.395 (2) | C17—H17A | 0.9800 |
C5—H5 | 0.9500 | C17—H17B | 0.9800 |
C6—C7 | 1.390 (2) | C17—H17C | 0.9800 |
C6—C9 | 1.4894 (19) | C18—H18A | 0.9800 |
C7—C8 | 1.388 (2) | C18—H18B | 0.9800 |
C7—H7 | 0.9500 | C18—H18C | 0.9800 |
C8—H8 | 0.9500 | | |
| | | |
C9—O2—C10 | 113.91 (11) | O2—C10—H10C | 109.5 |
N2—N1—C1 | 112.85 (11) | H10A—C10—H10C | 109.5 |
N1—N2—C11 | 113.33 (12) | H10B—C10—H10C | 109.5 |
C2—C1—N1 | 116.08 (12) | C16—C11—C12 | 120.15 (13) |
C2—C1—C3 | 121.77 (12) | C16—C11—N2 | 124.38 (13) |
N1—C1—C3 | 122.12 (12) | C12—C11—N2 | 115.46 (13) |
C1—C2—Cl2 | 124.19 (11) | C13—C12—C11 | 121.13 (14) |
C1—C2—Cl1 | 122.44 (11) | C13—C12—H12 | 119.4 |
Cl2—C2—Cl1 | 113.37 (8) | C11—C12—H12 | 119.4 |
C8—C3—C4 | 119.86 (13) | C12—C13—C14 | 118.70 (14) |
C8—C3—C1 | 119.43 (13) | C12—C13—C17 | 120.45 (15) |
C4—C3—C1 | 120.70 (13) | C14—C13—C17 | 120.84 (14) |
C5—C4—C3 | 119.96 (13) | C15—C14—C13 | 119.55 (13) |
C5—C4—H4 | 120.0 | C15—C14—C18 | 119.66 (15) |
C3—C4—H4 | 120.0 | C13—C14—C18 | 120.80 (15) |
C4—C5—C6 | 119.88 (13) | C16—C15—C14 | 121.71 (14) |
C4—C5—H5 | 120.1 | C16—C15—H15 | 119.1 |
C6—C5—H5 | 120.1 | C14—C15—H15 | 119.1 |
C7—C6—C5 | 119.93 (13) | C15—C16—C11 | 118.75 (14) |
C7—C6—C9 | 117.03 (13) | C15—C16—H16 | 120.6 |
C5—C6—C9 | 123.04 (13) | C11—C16—H16 | 120.6 |
C8—C7—C6 | 120.22 (13) | C13—C17—H17A | 109.5 |
C8—C7—H7 | 119.9 | C13—C17—H17B | 109.5 |
C6—C7—H7 | 119.9 | H17A—C17—H17B | 109.5 |
C7—C8—C3 | 120.10 (13) | C13—C17—H17C | 109.5 |
C7—C8—H8 | 119.9 | H17A—C17—H17C | 109.5 |
C3—C8—H8 | 119.9 | H17B—C17—H17C | 109.5 |
O1—C9—O2 | 123.20 (13) | C14—C18—H18A | 109.5 |
O1—C9—C6 | 124.17 (13) | C14—C18—H18B | 109.5 |
O2—C9—C6 | 112.64 (12) | H18A—C18—H18B | 109.5 |
O2—C10—H10A | 109.5 | C14—C18—H18C | 109.5 |
O2—C10—H10B | 109.5 | H18A—C18—H18C | 109.5 |
H10A—C10—H10B | 109.5 | H18B—C18—H18C | 109.5 |
| | | |
C1—N1—N2—C11 | 178.17 (11) | C10—O2—C9—O1 | 1.63 (19) |
N2—N1—C1—C2 | −175.79 (13) | C10—O2—C9—C6 | −178.38 (11) |
N2—N1—C1—C3 | 2.06 (19) | C7—C6—C9—O1 | 19.0 (2) |
N1—C1—C2—Cl2 | 1.1 (2) | C5—C6—C9—O1 | −161.01 (14) |
C3—C1—C2—Cl2 | −176.74 (11) | C7—C6—C9—O2 | −161.04 (12) |
N1—C1—C2—Cl1 | −178.69 (10) | C5—C6—C9—O2 | 19.00 (18) |
C3—C1—C2—Cl1 | 3.5 (2) | N1—N2—C11—C16 | −11.1 (2) |
C2—C1—C3—C8 | 67.37 (19) | N1—N2—C11—C12 | 170.08 (13) |
N1—C1—C3—C8 | −110.35 (15) | C16—C11—C12—C13 | 1.5 (2) |
C2—C1—C3—C4 | −113.54 (16) | N2—C11—C12—C13 | −179.65 (13) |
N1—C1—C3—C4 | 68.73 (18) | C11—C12—C13—C14 | −0.7 (2) |
C8—C3—C4—C5 | −2.2 (2) | C11—C12—C13—C17 | 179.96 (14) |
C1—C3—C4—C5 | 178.73 (12) | C12—C13—C14—C15 | 0.1 (2) |
C3—C4—C5—C6 | 1.3 (2) | C17—C13—C14—C15 | 179.40 (14) |
C4—C5—C6—C7 | 0.5 (2) | C12—C13—C14—C18 | −179.55 (14) |
C4—C5—C6—C9 | −179.51 (12) | C17—C13—C14—C18 | −0.2 (2) |
C5—C6—C7—C8 | −1.6 (2) | C13—C14—C15—C16 | −0.2 (2) |
C9—C6—C7—C8 | 178.48 (12) | C18—C14—C15—C16 | 179.48 (14) |
C6—C7—C8—C3 | 0.7 (2) | C14—C15—C16—C11 | 0.9 (2) |
C4—C3—C8—C7 | 1.2 (2) | C12—C11—C16—C15 | −1.5 (2) |
C1—C3—C8—C7 | −179.74 (12) | N2—C11—C16—C15 | 179.72 (13) |
Percentage contributions of interatomic contacts to the
Hirshfeld surface for the title compounds topContact | | Percentage contribution | |
| (I) | (II) | (III) |
H···H | 33.5 | 39.7 | 37.0 |
Cl···H/H···Cl | 20.5 | 14.4 | 19.1 |
C···H/H···C | 14.3 | 14.5 | 16.0 |
O···H/H···O | 8.1 | 6.6 | 8.7 |
C···C | 6.0 | 4.0 | 2.1 |
N···H/H···N | 4.2 | 5.2 | 4.9 |
N···C/C···N | 4.0 | 0.3 | 2.0 |
Cl···O/O···Cl | 3.7 | 2.6 | 1.5 |
Cl···C/C···Cl | 3.3 | 2.8 | 5.3 |
O···C/C···O | 1.7 | 4.6 | 1.4 |
Cl···Cl | 0.6 | 4.0 | 1.0 |
O···C/C···O | – | 1.1 | 1.4 |
Cl···N/N..Cl | – | 0.8 | 0.4 |
O···C/C···O | – | – | 0.2 |