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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024000732/wm5708sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000732/wm5708Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000732/wm5708IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000732/wm5708IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024000732/wm5708Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024000732/wm5708IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024000732/wm5708IIIsup7.cml
Supplementary material

CCDC references: 2327446; 2327447; 2327448

Computing details top

Methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate (I) top
Crystal data top
C16H12Cl2N2O2F(000) = 688
Mr = 335.18Dx = 1.510 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 15.47572 (16) ÅCell parameters from 12282 reflections
b = 4.16896 (4) Åθ = 2.9–77.0°
c = 23.2257 (2) ŵ = 4.04 mm1
β = 100.1964 (9)°T = 100 K
V = 1474.80 (2) Å3Prism, red
Z = 40.22 × 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 tubeRint = 0.060
φ and ω scansθmax = 77.8°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 1919
Tmin = 0.404, Tmax = 0.600k = 55
23940 measured reflectionsl = 2928
3151 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-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 reflectionsΔρmax = 0.46 e Å3
200 parametersΔρmin = 0.32 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.13479 (3)0.05540 (11)0.40331 (2)0.02247 (13)
Cl20.27874 (3)0.32473 (12)0.48326 (2)0.02639 (14)
O10.01936 (9)0.1723 (4)0.10978 (6)0.0285 (3)
O20.14455 (9)0.0786 (4)0.10100 (6)0.0268 (3)
N10.34295 (10)0.5658 (4)0.38299 (7)0.0216 (3)
N20.38242 (10)0.6368 (4)0.34161 (7)0.0211 (3)
C10.26399 (11)0.3911 (4)0.36605 (8)0.0207 (4)
C20.22931 (12)0.2761 (5)0.41127 (8)0.0214 (4)
C30.22169 (11)0.3354 (4)0.30397 (8)0.0197 (4)
C40.26794 (11)0.1764 (5)0.26603 (8)0.0210 (4)
H40.3276490.1194110.2790230.025*
C50.22744 (12)0.1012 (5)0.20969 (8)0.0220 (4)
H50.2590870.0111300.1845140.026*
C60.14025 (11)0.1895 (4)0.18962 (8)0.0203 (4)
C70.09485 (11)0.3596 (4)0.22649 (8)0.0215 (4)
H70.0362190.4271190.2126520.026*
C80.13490 (12)0.4308 (5)0.28326 (8)0.0220 (4)
H80.1033370.5447860.3082780.026*
C90.09401 (12)0.0996 (5)0.13000 (8)0.0215 (4)
C100.10264 (14)0.1883 (6)0.04358 (8)0.0293 (4)
H10A0.0875220.0031270.0177760.044*
H10B0.0491210.3072010.0469280.044*
H10C0.1429470.3288380.0272280.044*
C110.46037 (11)0.8199 (4)0.36040 (8)0.0209 (4)
C120.51605 (12)0.8486 (5)0.31977 (8)0.0228 (4)
H120.5007230.7512520.2823640.027*
C130.59408 (13)1.0194 (5)0.33381 (9)0.0255 (4)
H130.6321901.0381160.3060980.031*
C140.61616 (12)1.1624 (5)0.38829 (9)0.0258 (4)
H140.6701571.2745950.3983270.031*
C150.55900 (13)1.1414 (5)0.42850 (8)0.0264 (4)
H150.5734401.2452820.4653610.032*
C160.48136 (12)0.9698 (5)0.41483 (8)0.0233 (4)
H160.4427430.9544050.4422800.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0167 (2)0.0264 (2)0.0244 (2)0.00357 (16)0.00406 (15)0.00043 (16)
Cl20.0217 (2)0.0355 (3)0.0213 (2)0.00499 (17)0.00171 (16)0.00103 (17)
O10.0183 (6)0.0359 (8)0.0291 (7)0.0048 (6)0.0016 (5)0.0043 (6)
O20.0193 (6)0.0382 (8)0.0220 (6)0.0047 (6)0.0016 (5)0.0046 (6)
N10.0162 (7)0.0232 (8)0.0248 (7)0.0001 (6)0.0022 (6)0.0017 (6)
N20.0153 (7)0.0216 (7)0.0260 (8)0.0007 (6)0.0025 (6)0.0023 (6)
C10.0152 (8)0.0208 (8)0.0255 (9)0.0019 (7)0.0018 (7)0.0006 (7)
C20.0163 (8)0.0233 (9)0.0241 (9)0.0006 (7)0.0023 (6)0.0014 (7)
C30.0163 (8)0.0202 (8)0.0221 (9)0.0004 (7)0.0023 (6)0.0026 (7)
C40.0142 (8)0.0244 (9)0.0241 (9)0.0035 (7)0.0029 (6)0.0038 (7)
C50.0166 (8)0.0260 (9)0.0240 (9)0.0034 (7)0.0049 (7)0.0022 (7)
C60.0159 (8)0.0220 (9)0.0224 (8)0.0002 (7)0.0021 (6)0.0025 (7)
C70.0140 (8)0.0221 (9)0.0281 (9)0.0019 (7)0.0028 (7)0.0016 (7)
C80.0153 (8)0.0248 (9)0.0261 (9)0.0004 (7)0.0044 (7)0.0011 (7)
C90.0175 (8)0.0233 (9)0.0237 (9)0.0013 (7)0.0038 (7)0.0019 (7)
C100.0264 (10)0.0391 (11)0.0214 (9)0.0002 (8)0.0018 (7)0.0053 (8)
C110.0140 (8)0.0219 (9)0.0259 (9)0.0017 (7)0.0011 (6)0.0034 (7)
C120.0205 (9)0.0238 (9)0.0246 (9)0.0002 (7)0.0053 (7)0.0005 (7)
C130.0195 (9)0.0274 (10)0.0306 (10)0.0009 (8)0.0077 (7)0.0020 (8)
C140.0155 (8)0.0291 (10)0.0319 (10)0.0030 (7)0.0014 (7)0.0046 (8)
C150.0233 (9)0.0305 (10)0.0241 (9)0.0045 (8)0.0004 (7)0.0017 (8)
C160.0189 (9)0.0282 (9)0.0227 (9)0.0010 (7)0.0037 (7)0.0035 (7)
Geometric parameters (Å, º) top
Cl1—C21.7102 (19)C7—C81.386 (3)
Cl2—C21.7231 (18)C7—H70.9500
O1—C91.206 (2)C8—H80.9500
O2—C91.343 (2)C10—H10A0.9800
O2—C101.450 (2)C10—H10B0.9800
N1—N21.262 (2)C10—H10C0.9800
N1—C11.417 (2)C11—C121.391 (3)
N2—C111.429 (2)C11—C161.396 (3)
C1—C21.349 (3)C12—C131.390 (3)
C1—C31.492 (2)C12—H120.9500
C3—C41.397 (3)C13—C141.386 (3)
C3—C81.402 (2)C13—H130.9500
C4—C51.383 (3)C14—C151.398 (3)
C4—H40.9500C14—H140.9500
C5—C61.397 (2)C15—C161.386 (3)
C5—H50.9500C15—H150.9500
C6—C71.394 (3)C16—H160.9500
C6—C91.490 (3)
C9—O2—C10115.49 (15)O1—C9—O2123.12 (17)
N2—N1—C1114.77 (15)O1—C9—C6124.62 (17)
N1—N2—C11112.90 (15)O2—C9—C6112.26 (15)
C2—C1—N1114.12 (16)O2—C10—H10A109.5
C2—C1—C3121.99 (16)O2—C10—H10B109.5
N1—C1—C3123.89 (16)H10A—C10—H10B109.5
C1—C2—Cl1123.88 (14)O2—C10—H10C109.5
C1—C2—Cl2122.96 (14)H10A—C10—H10C109.5
Cl1—C2—Cl2113.11 (11)H10B—C10—H10C109.5
C4—C3—C8119.01 (16)C12—C11—C16120.20 (17)
C4—C3—C1119.81 (16)C12—C11—N2115.44 (16)
C8—C3—C1121.15 (16)C16—C11—N2124.36 (16)
C5—C4—C3120.48 (16)C13—C12—C11120.10 (18)
C5—C4—H4119.8C13—C12—H12119.9
C3—C4—H4119.8C11—C12—H12119.9
C4—C5—C6120.35 (17)C14—C13—C12119.88 (18)
C4—C5—H5119.8C14—C13—H13120.1
C6—C5—H5119.8C12—C13—H13120.1
C7—C6—C5119.42 (17)C13—C14—C15120.01 (18)
C7—C6—C9119.19 (16)C13—C14—H14120.0
C5—C6—C9121.38 (17)C15—C14—H14120.0
C8—C7—C6120.28 (16)C16—C15—C14120.30 (18)
C8—C7—H7119.9C16—C15—H15119.8
C6—C7—H7119.9C14—C15—H15119.8
C7—C8—C3120.38 (17)C15—C16—C11119.46 (17)
C7—C8—H8119.8C15—C16—H16120.3
C3—C8—H8119.8C11—C16—H16120.3
C1—N1—N2—C11178.44 (15)C4—C3—C8—C71.9 (3)
N2—N1—C1—C2170.71 (16)C1—C3—C8—C7176.03 (17)
N2—N1—C1—C39.2 (3)C10—O2—C9—O11.8 (3)
N1—C1—C2—Cl1179.62 (13)C10—O2—C9—C6177.22 (16)
C3—C1—C2—Cl10.3 (3)C7—C6—C9—O12.5 (3)
N1—C1—C2—Cl22.2 (2)C5—C6—C9—O1178.85 (19)
C3—C1—C2—Cl2177.66 (14)C7—C6—C9—O2176.46 (17)
C2—C1—C3—C4120.9 (2)C5—C6—C9—O22.2 (3)
N1—C1—C3—C459.0 (3)N1—N2—C11—C12167.20 (16)
C2—C1—C3—C857.0 (3)N1—N2—C11—C1614.1 (3)
N1—C1—C3—C8123.1 (2)C16—C11—C12—C131.8 (3)
C8—C3—C4—C52.9 (3)N2—C11—C12—C13179.43 (17)
C1—C3—C4—C5175.04 (17)C11—C12—C13—C140.3 (3)
C3—C4—C5—C61.4 (3)C12—C13—C14—C151.6 (3)
C4—C5—C6—C71.2 (3)C13—C14—C15—C162.0 (3)
C4—C5—C6—C9177.42 (17)C14—C15—C16—C110.5 (3)
C5—C6—C7—C82.2 (3)C12—C11—C16—C151.4 (3)
C9—C6—C7—C8176.44 (17)N2—C11—C16—C15179.91 (18)
C6—C7—C8—C30.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N2i0.952.543.191 (3)126
C5—H5···O20.952.402.726 (2)100
Symmetry code: (i) x, y1, z.
Methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate (II) top
Crystal data top
C17H14Cl2N2O2F(000) = 720
Mr = 349.20Dx = 1.420 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 15.6177 (2) ÅCell parameters from 12932 reflections
b = 8.47502 (11) Åθ = 3.0–77.0°
c = 13.10365 (17) ŵ = 3.67 mm1
β = 109.6555 (15)°T = 100 K
V = 1633.34 (4) Å3Prism, red
Z = 40.26 × 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 tubeRint = 0.054
φ and ω scansθmax = 78.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 1519
Tmin = 0.307, Tmax = 0.530k = 1010
28857 measured reflectionsl = 1616
3469 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.13Δρmax = 0.30 e Å3
3469 reflectionsΔρmin = 0.48 e Å3
211 parametersExtinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
Cl10.98647 (3)0.77109 (5)0.27683 (3)0.02442 (14)
Cl20.94376 (3)0.63249 (5)0.06421 (3)0.02432 (14)
O10.69644 (8)0.59702 (16)0.60175 (10)0.0264 (3)
O20.81960 (8)0.44134 (15)0.66154 (9)0.0245 (3)
N10.78451 (9)0.49845 (18)0.10125 (11)0.0209 (3)
N20.71406 (9)0.44374 (18)0.11566 (11)0.0219 (3)
C10.84094 (11)0.5841 (2)0.19136 (13)0.0199 (3)
C20.91421 (11)0.6533 (2)0.17879 (13)0.0210 (3)
C30.82373 (11)0.5849 (2)0.29668 (13)0.0196 (3)
C40.74921 (11)0.6634 (2)0.30912 (13)0.0216 (3)
H40.7105190.7252910.2515760.026*
C50.73197 (11)0.6504 (2)0.40622 (14)0.0220 (3)
H50.6821770.7055340.4155950.026*
C60.78742 (11)0.5568 (2)0.48977 (13)0.0195 (3)
C70.86273 (11)0.4802 (2)0.47817 (13)0.0208 (3)
H70.9013890.4180740.5356320.025*
C80.88054 (11)0.4957 (2)0.38166 (13)0.0207 (3)
H80.9320790.4447240.3736100.025*
C90.76178 (11)0.5361 (2)0.58862 (13)0.0204 (3)
C100.79809 (13)0.4119 (2)0.75872 (14)0.0275 (4)
H10A0.8399750.3326190.8029760.041*
H10B0.7355180.3730250.7390450.041*
H10C0.8041670.5100440.8001060.041*
C110.65821 (11)0.3536 (2)0.02710 (13)0.0215 (3)
C120.57409 (12)0.3086 (3)0.03265 (15)0.0296 (4)
H120.5562000.3432330.0914450.036*
C130.51651 (13)0.2138 (3)0.04704 (16)0.0314 (4)
H130.4588990.1851920.0430690.038*
C140.54206 (12)0.1597 (2)0.13325 (14)0.0249 (4)
C150.62625 (12)0.2063 (2)0.13829 (14)0.0233 (4)
H150.6442260.1712150.1969140.028*
C160.68413 (11)0.3026 (2)0.05973 (13)0.0217 (3)
H160.7410000.3337960.0647850.026*
C170.48059 (13)0.0527 (3)0.21805 (16)0.0337 (4)
H17A0.5169800.0292870.2368710.050*
H17B0.4482590.1143180.2828430.050*
H17C0.4364820.0032050.1897050.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0228 (2)0.0257 (2)0.0259 (2)0.00466 (15)0.00965 (16)0.00107 (15)
Cl20.0258 (2)0.0280 (2)0.0246 (2)0.00138 (15)0.01564 (16)0.00240 (15)
O10.0245 (6)0.0358 (7)0.0220 (6)0.0048 (5)0.0119 (5)0.0007 (5)
O20.0266 (6)0.0303 (7)0.0204 (6)0.0048 (5)0.0131 (5)0.0057 (5)
N10.0212 (6)0.0230 (7)0.0204 (6)0.0009 (5)0.0094 (5)0.0002 (5)
N20.0223 (7)0.0248 (7)0.0202 (7)0.0011 (6)0.0093 (5)0.0005 (6)
C10.0209 (7)0.0203 (8)0.0200 (8)0.0022 (6)0.0087 (6)0.0015 (6)
C20.0219 (8)0.0212 (8)0.0214 (8)0.0017 (6)0.0092 (6)0.0008 (6)
C30.0206 (7)0.0205 (8)0.0197 (8)0.0039 (6)0.0095 (6)0.0019 (6)
C40.0213 (8)0.0228 (8)0.0209 (8)0.0013 (6)0.0075 (6)0.0026 (6)
C50.0209 (8)0.0231 (8)0.0246 (8)0.0008 (6)0.0112 (6)0.0010 (6)
C60.0206 (7)0.0205 (8)0.0188 (7)0.0028 (6)0.0086 (6)0.0019 (6)
C70.0199 (7)0.0228 (8)0.0206 (7)0.0001 (6)0.0079 (6)0.0009 (6)
C80.0200 (7)0.0221 (8)0.0221 (8)0.0009 (6)0.0099 (6)0.0030 (6)
C90.0199 (7)0.0223 (8)0.0201 (7)0.0026 (6)0.0081 (6)0.0032 (6)
C100.0323 (9)0.0340 (10)0.0210 (8)0.0027 (8)0.0153 (7)0.0043 (7)
C110.0227 (8)0.0230 (8)0.0196 (8)0.0004 (6)0.0081 (6)0.0001 (6)
C120.0265 (9)0.0407 (11)0.0261 (9)0.0058 (8)0.0146 (7)0.0065 (8)
C130.0238 (8)0.0438 (12)0.0302 (9)0.0093 (8)0.0138 (7)0.0067 (8)
C140.0260 (8)0.0256 (9)0.0226 (8)0.0018 (7)0.0076 (7)0.0007 (7)
C150.0273 (8)0.0244 (9)0.0206 (8)0.0019 (7)0.0112 (7)0.0008 (7)
C160.0222 (8)0.0236 (8)0.0214 (8)0.0002 (6)0.0101 (6)0.0015 (7)
C170.0319 (9)0.0391 (11)0.0300 (9)0.0093 (8)0.0105 (8)0.0090 (8)
Geometric parameters (Å, º) top
Cl1—C21.7159 (17)C7—H70.9500
Cl2—C21.7217 (16)C8—H80.9500
O1—C91.207 (2)C10—H10A0.9800
O2—C91.339 (2)C10—H10B0.9800
O2—C101.4438 (19)C10—H10C0.9800
N1—N21.265 (2)C11—C121.393 (2)
N1—C11.414 (2)C11—C161.398 (2)
N2—C111.418 (2)C12—C131.383 (3)
C1—C21.345 (2)C12—H120.9500
C1—C31.492 (2)C13—C141.396 (3)
C3—C81.391 (2)C13—H130.9500
C3—C41.397 (2)C14—C151.396 (2)
C4—C51.391 (2)C14—C171.504 (2)
C4—H40.9500C15—C161.385 (2)
C5—C61.393 (2)C15—H150.9500
C5—H50.9500C16—H160.9500
C6—C71.396 (2)C17—H17A0.9800
C6—C91.489 (2)C17—H17B0.9800
C7—C81.389 (2)C17—H17C0.9800
C9—O2—C10115.59 (13)O2—C10—H10A109.5
N2—N1—C1113.13 (13)O2—C10—H10B109.5
N1—N2—C11113.70 (13)H10A—C10—H10B109.5
C2—C1—N1116.03 (14)O2—C10—H10C109.5
C2—C1—C3122.48 (15)H10A—C10—H10C109.5
N1—C1—C3121.28 (14)H10B—C10—H10C109.5
C1—C2—Cl1122.31 (13)C12—C11—C16119.63 (16)
C1—C2—Cl2123.43 (13)C12—C11—N2115.85 (15)
Cl1—C2—Cl2114.26 (9)C16—C11—N2124.45 (15)
C8—C3—C4119.85 (15)C13—C12—C11120.30 (16)
C8—C3—C1118.23 (14)C13—C12—H12119.8
C4—C3—C1121.77 (15)C11—C12—H12119.8
C5—C4—C3119.63 (15)C12—C13—C14120.76 (16)
C5—C4—H4120.2C12—C13—H13119.6
C3—C4—H4120.2C14—C13—H13119.6
C4—C5—C6120.25 (15)C15—C14—C13118.40 (16)
C4—C5—H5119.9C15—C14—C17120.88 (16)
C6—C5—H5119.9C13—C14—C17120.72 (16)
C5—C6—C7120.22 (14)C16—C15—C14121.44 (15)
C5—C6—C9118.22 (14)C16—C15—H15119.3
C7—C6—C9121.52 (15)C14—C15—H15119.3
C8—C7—C6119.28 (15)C15—C16—C11119.45 (15)
C8—C7—H7120.4C15—C16—H16120.3
C6—C7—H7120.4C11—C16—H16120.3
C7—C8—C3120.73 (15)C14—C17—H17A109.5
C7—C8—H8119.6C14—C17—H17B109.5
C3—C8—H8119.6H17A—C17—H17B109.5
O1—C9—O2123.68 (15)C14—C17—H17C109.5
O1—C9—C6124.15 (15)H17A—C17—H17C109.5
O2—C9—C6112.17 (13)H17B—C17—H17C109.5
C1—N1—N2—C11178.24 (14)C1—C3—C8—C7173.98 (15)
N2—N1—C1—C2176.18 (15)C10—O2—C9—O11.4 (2)
N2—N1—C1—C38.9 (2)C10—O2—C9—C6178.45 (14)
N1—C1—C2—Cl1176.23 (12)C5—C6—C9—O11.0 (3)
C3—C1—C2—Cl18.9 (2)C7—C6—C9—O1178.47 (17)
N1—C1—C2—Cl23.7 (2)C5—C6—C9—O2178.82 (14)
C3—C1—C2—Cl2171.16 (13)C7—C6—C9—O21.4 (2)
C2—C1—C3—C869.6 (2)N1—N2—C11—C12171.71 (16)
N1—C1—C3—C8104.94 (19)N1—N2—C11—C1611.5 (2)
C2—C1—C3—C4114.81 (19)C16—C11—C12—C130.1 (3)
N1—C1—C3—C470.6 (2)N2—C11—C12—C13176.77 (18)
C8—C3—C4—C50.6 (2)C11—C12—C13—C141.0 (3)
C1—C3—C4—C5174.91 (16)C12—C13—C14—C151.3 (3)
C3—C4—C5—C61.5 (3)C12—C13—C14—C17178.15 (19)
C4—C5—C6—C72.4 (3)C13—C14—C15—C160.6 (3)
C4—C5—C6—C9175.06 (15)C17—C14—C15—C16178.87 (17)
C5—C6—C7—C81.3 (2)C14—C15—C16—C110.5 (3)
C9—C6—C7—C8176.06 (15)C12—C11—C16—C150.9 (3)
C6—C7—C8—C30.7 (3)N2—C11—C16—C15175.78 (16)
C4—C3—C8—C71.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.952.433.268 (2)148
C13—H13···O1ii0.952.403.309 (3)159
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y1/2, z+1/2.
Methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate (III) top
Crystal data top
C18H16Cl2N2O2Z = 2
Mr = 363.23F(000) = 376
Triclinic, P1Dx = 1.412 Mg m3
a = 8.22057 (10) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.53211 (9) ÅCell parameters from 14210 reflections
c = 13.08729 (14) Åθ = 3.6–77.0°
α = 103.9484 (9)°µ = 3.53 mm1
β = 101.9047 (10)°T = 100 K
γ = 98.0600 (9)°Prism, red
V = 854.09 (2) Å30.20 × 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 tubeRint = 0.063
φ and ω scansθmax = 77.8°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 1010
Tmin = 0.349, Tmax = 0.700k = 810
29808 measured reflectionsl = 1616
3632 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-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 reflectionsΔρmax = 0.31 e Å3
220 parametersΔρmin = 0.46 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.07283 (5)0.14861 (4)0.77715 (3)0.02444 (11)
Cl20.13915 (5)0.31047 (4)0.57534 (3)0.02637 (12)
O10.30977 (14)0.68544 (14)1.04185 (9)0.0315 (3)
O20.04043 (13)0.67433 (12)0.95696 (8)0.0208 (2)
N10.21612 (15)0.01951 (15)0.54534 (10)0.0198 (2)
N20.26094 (15)0.16265 (15)0.53648 (10)0.0208 (3)
C10.17177 (17)0.02110 (17)0.64440 (11)0.0189 (3)
C20.13347 (18)0.12681 (18)0.66254 (11)0.0206 (3)
C30.17331 (18)0.17742 (17)0.72590 (11)0.0185 (3)
C40.05481 (18)0.27494 (17)0.70373 (11)0.0203 (3)
H40.0264570.2429880.6355540.024*
C50.05592 (18)0.41897 (17)0.78162 (12)0.0203 (3)
H50.0260720.4841810.7672600.024*
C60.17767 (17)0.46736 (17)0.88079 (11)0.0188 (3)
C70.29835 (18)0.37242 (17)0.90121 (11)0.0202 (3)
H70.3829300.4068720.9680320.024*
C80.29570 (18)0.22742 (17)0.82428 (12)0.0202 (3)
H80.3776510.1622760.8389000.024*
C90.18624 (18)0.61892 (17)0.96841 (12)0.0209 (3)
C100.0464 (2)0.82424 (18)1.03931 (12)0.0244 (3)
H10A0.0632700.8581601.0254270.037*
H10B0.1357200.9115181.0370930.037*
H10C0.0707720.8045281.1111500.037*
C110.31099 (18)0.16259 (18)0.43840 (11)0.0207 (3)
C120.33518 (19)0.31514 (18)0.41637 (12)0.0232 (3)
H120.3185470.4093550.4660000.028*
C130.38330 (18)0.3316 (2)0.32285 (13)0.0249 (3)
C140.40929 (18)0.1914 (2)0.25099 (12)0.0258 (3)
C150.38626 (19)0.0399 (2)0.27461 (12)0.0260 (3)
H150.4037290.0545270.2255810.031*
C160.33864 (19)0.02371 (19)0.36759 (12)0.0231 (3)
H160.3250380.0799760.3829230.028*
C170.4088 (2)0.4974 (2)0.30023 (15)0.0333 (4)
H17A0.3762390.5782060.3554580.050*
H17B0.3382630.4888340.2281490.050*
H17C0.5284070.5329260.3023860.050*
C180.4627 (2)0.2029 (3)0.14898 (14)0.0363 (4)
H18A0.3770110.2427300.1033530.055*
H18B0.4739090.0936880.1088170.055*
H18C0.5719960.2796120.1685420.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0346 (2)0.02094 (19)0.02065 (18)0.00298 (14)0.01118 (14)0.00900 (14)
Cl20.0402 (2)0.01643 (18)0.02316 (19)0.00645 (14)0.01064 (15)0.00402 (13)
O10.0278 (6)0.0277 (6)0.0306 (6)0.0074 (5)0.0038 (5)0.0053 (5)
O20.0259 (5)0.0182 (5)0.0211 (5)0.0070 (4)0.0100 (4)0.0059 (4)
N10.0231 (6)0.0194 (6)0.0185 (6)0.0034 (5)0.0077 (5)0.0066 (5)
N20.0240 (6)0.0199 (6)0.0198 (6)0.0025 (5)0.0092 (5)0.0060 (5)
C10.0214 (6)0.0188 (7)0.0171 (6)0.0034 (5)0.0071 (5)0.0044 (5)
C20.0251 (7)0.0191 (7)0.0180 (6)0.0041 (5)0.0070 (5)0.0049 (5)
C30.0234 (7)0.0164 (6)0.0187 (6)0.0017 (5)0.0108 (5)0.0069 (5)
C40.0247 (7)0.0203 (7)0.0174 (6)0.0040 (5)0.0071 (5)0.0070 (5)
C50.0242 (7)0.0190 (7)0.0216 (7)0.0063 (5)0.0097 (6)0.0088 (5)
C60.0234 (7)0.0170 (6)0.0189 (7)0.0029 (5)0.0103 (5)0.0067 (5)
C70.0216 (7)0.0204 (7)0.0186 (6)0.0020 (5)0.0063 (5)0.0056 (5)
C80.0227 (7)0.0191 (7)0.0218 (7)0.0060 (5)0.0093 (5)0.0070 (5)
C90.0248 (7)0.0194 (7)0.0219 (7)0.0050 (5)0.0105 (6)0.0079 (6)
C100.0337 (8)0.0179 (7)0.0262 (7)0.0080 (6)0.0152 (6)0.0066 (6)
C110.0212 (7)0.0231 (7)0.0190 (7)0.0025 (5)0.0085 (5)0.0063 (6)
C120.0247 (7)0.0226 (7)0.0230 (7)0.0022 (6)0.0084 (6)0.0069 (6)
C130.0214 (7)0.0299 (8)0.0252 (7)0.0006 (6)0.0064 (6)0.0129 (6)
C140.0206 (7)0.0376 (9)0.0214 (7)0.0024 (6)0.0085 (6)0.0114 (6)
C150.0245 (7)0.0313 (8)0.0235 (7)0.0052 (6)0.0119 (6)0.0049 (6)
C160.0247 (7)0.0226 (7)0.0244 (7)0.0042 (6)0.0108 (6)0.0072 (6)
C170.0366 (9)0.0343 (9)0.0335 (9)0.0011 (7)0.0109 (7)0.0192 (7)
C180.0376 (9)0.0506 (11)0.0260 (8)0.0047 (8)0.0162 (7)0.0157 (8)
Geometric parameters (Å, º) top
Cl1—C21.7176 (14)C10—H10A0.9800
Cl2—C21.7148 (14)C10—H10B0.9800
O1—C91.2041 (19)C10—H10C0.9800
O2—C91.3422 (17)C11—C161.396 (2)
O2—C101.4478 (17)C11—C121.396 (2)
N1—N21.2651 (17)C12—C131.393 (2)
N1—C11.4148 (17)C12—H120.9500
N2—C111.4263 (17)C13—C141.404 (2)
C1—C21.346 (2)C13—C171.509 (2)
C1—C31.4901 (19)C14—C151.397 (2)
C3—C81.390 (2)C14—C181.509 (2)
C3—C41.397 (2)C15—C161.384 (2)
C4—C51.392 (2)C15—H150.9500
C4—H40.9500C16—H160.9500
C5—C61.395 (2)C17—H17A0.9800
C5—H50.9500C17—H17B0.9800
C6—C71.390 (2)C17—H17C0.9800
C6—C91.4894 (19)C18—H18A0.9800
C7—C81.388 (2)C18—H18B0.9800
C7—H70.9500C18—H18C0.9800
C8—H80.9500
C9—O2—C10113.91 (11)O2—C10—H10C109.5
N2—N1—C1112.85 (11)H10A—C10—H10C109.5
N1—N2—C11113.33 (12)H10B—C10—H10C109.5
C2—C1—N1116.08 (12)C16—C11—C12120.15 (13)
C2—C1—C3121.77 (12)C16—C11—N2124.38 (13)
N1—C1—C3122.12 (12)C12—C11—N2115.46 (13)
C1—C2—Cl2124.19 (11)C13—C12—C11121.13 (14)
C1—C2—Cl1122.44 (11)C13—C12—H12119.4
Cl2—C2—Cl1113.37 (8)C11—C12—H12119.4
C8—C3—C4119.86 (13)C12—C13—C14118.70 (14)
C8—C3—C1119.43 (13)C12—C13—C17120.45 (15)
C4—C3—C1120.70 (13)C14—C13—C17120.84 (14)
C5—C4—C3119.96 (13)C15—C14—C13119.55 (13)
C5—C4—H4120.0C15—C14—C18119.66 (15)
C3—C4—H4120.0C13—C14—C18120.80 (15)
C4—C5—C6119.88 (13)C16—C15—C14121.71 (14)
C4—C5—H5120.1C16—C15—H15119.1
C6—C5—H5120.1C14—C15—H15119.1
C7—C6—C5119.93 (13)C15—C16—C11118.75 (14)
C7—C6—C9117.03 (13)C15—C16—H16120.6
C5—C6—C9123.04 (13)C11—C16—H16120.6
C8—C7—C6120.22 (13)C13—C17—H17A109.5
C8—C7—H7119.9C13—C17—H17B109.5
C6—C7—H7119.9H17A—C17—H17B109.5
C7—C8—C3120.10 (13)C13—C17—H17C109.5
C7—C8—H8119.9H17A—C17—H17C109.5
C3—C8—H8119.9H17B—C17—H17C109.5
O1—C9—O2123.20 (13)C14—C18—H18A109.5
O1—C9—C6124.17 (13)C14—C18—H18B109.5
O2—C9—C6112.64 (12)H18A—C18—H18B109.5
O2—C10—H10A109.5C14—C18—H18C109.5
O2—C10—H10B109.5H18A—C18—H18C109.5
H10A—C10—H10B109.5H18B—C18—H18C109.5
C1—N1—N2—C11178.17 (11)C10—O2—C9—O11.63 (19)
N2—N1—C1—C2175.79 (13)C10—O2—C9—C6178.38 (11)
N2—N1—C1—C32.06 (19)C7—C6—C9—O119.0 (2)
N1—C1—C2—Cl21.1 (2)C5—C6—C9—O1161.01 (14)
C3—C1—C2—Cl2176.74 (11)C7—C6—C9—O2161.04 (12)
N1—C1—C2—Cl1178.69 (10)C5—C6—C9—O219.00 (18)
C3—C1—C2—Cl13.5 (2)N1—N2—C11—C1611.1 (2)
C2—C1—C3—C867.37 (19)N1—N2—C11—C12170.08 (13)
N1—C1—C3—C8110.35 (15)C16—C11—C12—C131.5 (2)
C2—C1—C3—C4113.54 (16)N2—C11—C12—C13179.65 (13)
N1—C1—C3—C468.73 (18)C11—C12—C13—C140.7 (2)
C8—C3—C4—C52.2 (2)C11—C12—C13—C17179.96 (14)
C1—C3—C4—C5178.73 (12)C12—C13—C14—C150.1 (2)
C3—C4—C5—C61.3 (2)C17—C13—C14—C15179.40 (14)
C4—C5—C6—C70.5 (2)C12—C13—C14—C18179.55 (14)
C4—C5—C6—C9179.51 (12)C17—C13—C14—C180.2 (2)
C5—C6—C7—C81.6 (2)C13—C14—C15—C160.2 (2)
C9—C6—C7—C8178.48 (12)C18—C14—C15—C16179.48 (14)
C6—C7—C8—C30.7 (2)C14—C15—C16—C110.9 (2)
C4—C3—C8—C71.2 (2)C12—C11—C16—C151.5 (2)
C1—C3—C8—C7179.74 (12)N2—C11—C16—C15179.72 (13)
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compounds top
ContactPercentage contribution
(I)(II)(III)
H···H33.539.737.0
Cl···H/H···Cl20.514.419.1
C···H/H···C14.314.516.0
O···H/H···O8.16.68.7
C···C6.04.02.1
N···H/H···N4.25.24.9
N···C/C···N4.00.32.0
Cl···O/O···Cl3.72.61.5
Cl···C/C···Cl3.32.85.3
O···C/C···O1.74.61.4
Cl···Cl0.64.01.0
O···C/C···O1.11.4
Cl···N/N..Cl0.80.4
O···C/C···O0.2
 

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