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Sixteen N-isonicotinoyl arylaldehydehydrazones, NC5H4CONHN=CHC6H4R, have been studied and the structures of 14 of them have been determined, including the unsubstituted parent compound with R = H, and the complete sets of 2-, 3- and 4-substituted geometric isomers for R = F, Br and OMe, and two of the three isomers for R = Cl and OEt. The 2-chloro and 3-chloro derivatives are isostructural with the corresponding bromo isomers, and all compounds contain trans amide groups apart from the isostructural pair where R = 2-Cl and 2-Br, which contain cis amide groups. The structures exhibit a wide range of direction-specific intermolecular interactions, including eight types of hydrogen bonds, N—H...N, N—H...O, O—H...O, O—H...N, C—H...N, C—H...O, C—H...π(arene) and C—H...π(pyridyl), as well as π...π stacking interactions. The structures exhibit a very broad range of combinations of these interactions: the resulting hydrogen-bonded supramolecular structures range from one-dimensional when R = 2-F, 2-OMe or 2-OEt, via two-dimensional when R = 4-F, 3-Cl, 3-Br, 4-OMe or 3-OEt, to three-dimensional when R = H, 3-F, 2-Cl, 2-Br, 4-Br or 3-OMe. Minor changes in either the identity of the substituent or its location can lead to substantial changes in the pattern of supramolecular aggregation, posing significant problems of predictability. The new structures are compared with the recently published structures of the isomeric series having R = NO2, with several monosubstituted analogues containing 2-pyridyl or 3-pyridyl units rather than 4-pyridyl, and with a number of examples having two or three substituents in the aryl ring: some 30 structures in all are discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107036270/bm5048sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VIII, IX, X, XI, XII, XIII, XIV, XV

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048Isup2.fcf
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048IIsup3.fcf
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048IIIsup4.fcf
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048IVsup5.fcf
Contains datablock IV

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048Vsup6.fcf
Contains datablock V

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048VIsup7.fcf
Contains datablock VI

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048VIIIsup8.fcf
Contains datablock VIII

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048IXsup9.fcf
Contains datablock IX

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048Xsup10.fcf
Contains datablock X

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048XIsup11.fcf
Contains datablock XI

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048XIIsup12.fcf
Contains datablock XII

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048XIIIsup13.fcf
Contains datablock XIII

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048XIVsup14.fcf
Contains datablock XIV

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768107036270/bm5048XVsup15.fcf
Contains datablock XV

CCDC references: 671581; 671582; 671583; 671584; 671585; 671586; 671587; 671588; 671589; 671590; 671591; 671592; 671593; 671594

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) & SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 & PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
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[Figure 5]
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[Figure 8]
In full text version
(I) N-isonicotinoyl benzaldehydehydrazone top
Crystal data top
C13H11N3OF(000) = 1888
Mr = 225.25Dx = 1.367 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4964 reflections
a = 7.1927 (2) Åθ = 3.4–27.5°
b = 21.2168 (7) ŵ = 0.09 mm1
c = 28.6771 (10) ÅT = 120 K
V = 4376.3 (2) Å3Block, colourless
Z = 160.50 × 0.25 × 0.20 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
4964 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.4°
ϕ & ω scansh = 95
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 2727
Tmin = 0.966, Tmax = 0.982l = 3437
24117 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0763P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4964 reflectionsΔρmax = 0.42 e Å3
308 parametersΔρmin = 0.48 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (8)
Crystal data top
C13H11N3OV = 4376.3 (2) Å3
Mr = 225.25Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 7.1927 (2) ŵ = 0.09 mm1
b = 21.2168 (7) ÅT = 120 K
c = 28.6771 (10) Å0.50 × 0.25 × 0.20 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
4964 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3331 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.982Rint = 0.050
24117 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.05Δρmax = 0.42 e Å3
4964 reflectionsΔρmin = 0.48 e Å3
308 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.30732 (18)0.89156 (6)0.36805 (5)0.0218 (3)
C120.2246 (2)0.83490 (7)0.36854 (6)0.0215 (4)
C130.2290 (2)0.79380 (7)0.40621 (6)0.0213 (4)
C140.3232 (2)0.81130 (7)0.44618 (6)0.0185 (4)
C150.4038 (2)0.87097 (7)0.44693 (6)0.0211 (4)
C160.3932 (2)0.90872 (8)0.40765 (6)0.0221 (4)
C170.3434 (2)0.77007 (7)0.48849 (6)0.0215 (4)
O10.36608 (18)0.79234 (5)0.52721 (4)0.0316 (3)
N170.33990 (19)0.70717 (6)0.47865 (5)0.0215 (3)
N270.34698 (18)0.66458 (6)0.51498 (5)0.0216 (3)
C270.3407 (2)0.60626 (7)0.50285 (6)0.0208 (4)
C210.3361 (2)0.55639 (7)0.53793 (6)0.0195 (4)
C220.2853 (2)0.49525 (7)0.52464 (6)0.0235 (4)
C230.2727 (2)0.44764 (7)0.55815 (6)0.0255 (4)
C240.3081 (2)0.46062 (7)0.60447 (7)0.0252 (4)
C250.3610 (2)0.52110 (7)0.61772 (7)0.0262 (4)
C260.3759 (2)0.56842 (7)0.58466 (6)0.0232 (4)
N310.27932 (19)0.64135 (6)0.38413 (5)0.0230 (3)
C320.1632 (2)0.59217 (7)0.38168 (6)0.0217 (4)
C330.1536 (2)0.55171 (7)0.34394 (6)0.0197 (4)
C340.2726 (2)0.56107 (7)0.30643 (6)0.0189 (4)
C350.3915 (2)0.61300 (7)0.30806 (6)0.0230 (4)
C360.3888 (2)0.65142 (7)0.34690 (6)0.0234 (4)
C370.2776 (2)0.51940 (7)0.26428 (6)0.0214 (4)
O30.31675 (18)0.54004 (5)0.22580 (4)0.0296 (3)
N370.23655 (19)0.45787 (6)0.27330 (5)0.0213 (3)
N470.24051 (18)0.41517 (6)0.23713 (5)0.0216 (3)
C470.1826 (2)0.35949 (7)0.24720 (6)0.0202 (4)
C410.1828 (2)0.30983 (7)0.21188 (6)0.0201 (4)
C420.1062 (2)0.25101 (8)0.22278 (6)0.0242 (4)
C430.0967 (2)0.20405 (7)0.18906 (7)0.0266 (4)
C440.1613 (2)0.21547 (7)0.14450 (6)0.0238 (4)
C450.2408 (2)0.27344 (7)0.13361 (6)0.0230 (4)
C460.2536 (2)0.31989 (7)0.16711 (6)0.0209 (4)
H120.15900.82210.34140.026*
H130.16800.75420.40450.026*
H150.46540.88560.47410.025*
H160.44990.94910.40880.027*
H170.33330.69400.44960.026*
H270.33900.59550.47070.025*
H220.25950.48610.49290.028*
H230.23960.40610.54900.031*
H240.29640.42840.62720.030*
H250.38710.53000.64950.031*
H260.41350.60950.59390.028*
H320.08280.58460.40740.026*
H330.06680.51800.34370.024*
H350.47320.62180.28280.028*
H360.46890.68700.34730.028*
H370.20800.44560.30170.026*
H470.13930.35060.27780.024*
H420.06050.24320.25330.029*
H430.04560.16410.19670.032*
H440.15150.18370.12130.029*
H450.28630.28100.10300.028*
H460.31080.35900.15970.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0231 (8)0.0229 (7)0.0195 (8)0.0018 (5)0.0016 (6)0.0019 (6)
C120.0235 (9)0.0235 (8)0.0176 (9)0.0007 (6)0.0030 (7)0.0008 (7)
C130.0218 (9)0.0201 (8)0.0221 (10)0.0003 (6)0.0006 (7)0.0010 (7)
C140.0205 (9)0.0178 (7)0.0170 (9)0.0025 (6)0.0015 (7)0.0009 (7)
C150.0224 (9)0.0208 (8)0.0201 (10)0.0013 (6)0.0016 (7)0.0016 (7)
C160.0240 (9)0.0206 (8)0.0218 (10)0.0021 (6)0.0003 (7)0.0009 (7)
C170.0242 (9)0.0206 (8)0.0196 (10)0.0012 (6)0.0004 (7)0.0002 (7)
O10.0527 (8)0.0231 (6)0.0188 (7)0.0014 (5)0.0032 (6)0.0007 (5)
N170.0307 (8)0.0182 (7)0.0156 (8)0.0004 (6)0.0012 (6)0.0022 (6)
N270.0264 (8)0.0189 (7)0.0195 (8)0.0010 (5)0.0000 (6)0.0036 (6)
C270.0235 (9)0.0212 (8)0.0176 (9)0.0019 (6)0.0003 (7)0.0007 (7)
C210.0177 (8)0.0199 (8)0.0211 (10)0.0019 (6)0.0032 (7)0.0003 (7)
C220.0285 (10)0.0205 (8)0.0217 (10)0.0004 (6)0.0006 (7)0.0023 (7)
C230.0282 (10)0.0185 (8)0.0297 (11)0.0000 (6)0.0036 (8)0.0004 (7)
C240.0250 (9)0.0219 (8)0.0287 (11)0.0030 (6)0.0002 (8)0.0078 (8)
C250.0310 (10)0.0257 (9)0.0220 (10)0.0023 (7)0.0050 (8)0.0028 (8)
C260.0274 (9)0.0195 (8)0.0226 (10)0.0001 (6)0.0043 (7)0.0003 (7)
N310.0275 (8)0.0203 (7)0.0211 (8)0.0006 (5)0.0034 (6)0.0022 (6)
C320.0250 (9)0.0207 (8)0.0193 (9)0.0000 (6)0.0017 (7)0.0007 (7)
C330.0237 (9)0.0172 (7)0.0182 (9)0.0001 (6)0.0010 (7)0.0010 (7)
C340.0213 (9)0.0171 (7)0.0183 (9)0.0027 (6)0.0019 (7)0.0012 (7)
C350.0249 (9)0.0211 (8)0.0231 (10)0.0010 (6)0.0036 (7)0.0032 (7)
C360.0251 (9)0.0193 (8)0.0257 (10)0.0030 (6)0.0024 (7)0.0009 (7)
C370.0237 (9)0.0205 (8)0.0199 (10)0.0016 (6)0.0002 (7)0.0016 (7)
O30.0447 (8)0.0259 (6)0.0182 (7)0.0034 (5)0.0062 (6)0.0009 (5)
N370.0305 (8)0.0179 (7)0.0154 (8)0.0009 (5)0.0021 (6)0.0020 (6)
N470.0274 (8)0.0206 (7)0.0168 (8)0.0014 (5)0.0005 (6)0.0045 (6)
C470.0233 (9)0.0229 (8)0.0144 (9)0.0001 (6)0.0026 (7)0.0007 (7)
C410.0200 (9)0.0200 (8)0.0203 (10)0.0023 (6)0.0039 (7)0.0011 (7)
C420.0298 (9)0.0234 (8)0.0193 (10)0.0024 (7)0.0013 (7)0.0025 (7)
C430.0315 (10)0.0189 (8)0.0294 (11)0.0046 (7)0.0017 (8)0.0002 (8)
C440.0258 (9)0.0212 (8)0.0243 (10)0.0031 (6)0.0033 (7)0.0047 (7)
C450.0236 (9)0.0249 (8)0.0205 (10)0.0038 (6)0.0021 (7)0.0012 (7)
C460.0222 (9)0.0193 (8)0.0213 (10)0.0004 (6)0.0001 (7)0.0011 (7)
Geometric parameters (Å, º) top
N11—C121.341 (2)N31—C321.338 (2)
N11—C161.343 (2)N31—C361.344 (2)
C12—C131.389 (2)C32—C331.383 (2)
C12—H120.95C32—H320.95
C13—C141.382 (2)C33—C341.389 (2)
C13—H130.95C33—H330.95
C14—C151.392 (2)C34—C351.396 (2)
C14—C171.503 (2)C34—C371.498 (2)
C15—C161.384 (2)C35—C361.380 (2)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.218 (2)C37—O31.220 (2)
C17—N171.3642 (19)C37—N371.3632 (19)
N17—N271.3800 (18)N37—N471.3776 (18)
N17—H170.88N37—H370.88
N27—C271.2862 (19)N47—C471.2857 (19)
C27—C211.460 (2)C47—C411.462 (2)
C27—H270.95C47—H470.95
C21—C261.394 (2)C41—C461.397 (2)
C21—C221.401 (2)C41—C421.400 (2)
C22—C231.397 (2)C42—C431.390 (2)
C22—H220.95C42—H420.95
C23—C241.380 (2)C43—C441.381 (2)
C23—H230.95C43—H430.95
C24—C251.391 (2)C44—C451.392 (2)
C24—H240.95C44—H440.95
C25—C261.385 (2)C45—C461.379 (2)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
C12—N11—C16115.97 (14)C32—N31—C36116.61 (15)
N11—C12—C13124.12 (16)N31—C32—C33123.79 (16)
N11—C12—H12117.9N31—C32—H32118.1
C13—C12—H12117.9C33—C32—H32118.1
C14—C13—C12119.18 (15)C32—C33—C34119.12 (15)
C14—C13—H13120.4C32—C33—H33120.4
C12—C13—H13120.4C34—C33—H33120.4
C13—C14—C15117.46 (15)C33—C34—C35117.68 (15)
C13—C14—C17124.08 (14)C33—C34—C37123.75 (14)
C15—C14—C17118.46 (15)C35—C34—C37118.56 (15)
C16—C15—C14119.37 (16)C36—C35—C34118.97 (16)
C16—C15—H15120.3C36—C35—H35120.5
C14—C15—H15120.3C34—C35—H35120.5
N11—C16—C15123.83 (15)N31—C36—C35123.76 (15)
N11—C16—H16118.1N31—C36—H36118.1
C15—C16—H16118.1C35—C36—H36118.1
O1—C17—N17124.78 (16)O3—C37—N37124.42 (16)
O1—C17—C14121.55 (14)O3—C37—C34121.58 (14)
N17—C17—C14113.63 (15)N37—C37—C34114.00 (15)
C17—N17—N27118.94 (14)C37—N37—N47118.84 (14)
C17—N17—H17120.5C37—N37—H37120.6
N27—N17—H17120.5N47—N37—H37120.6
C27—N27—N17115.13 (14)C47—N47—N37115.36 (14)
N27—C27—C21120.77 (16)N47—C47—C41120.41 (16)
N27—C27—H27119.6N47—C47—H47119.8
C21—C27—H27119.6C41—C47—H47119.8
C26—C21—C22118.99 (15)C46—C41—C42119.00 (15)
C26—C21—C27121.68 (14)C46—C41—C47121.81 (14)
C22—C21—C27119.30 (16)C42—C41—C47119.17 (16)
C23—C22—C21119.95 (17)C43—C42—C41120.19 (16)
C23—C22—H22120.0C43—C42—H42119.9
C21—C22—H22120.0C41—C42—H42119.9
C24—C23—C22120.38 (16)C44—C43—C42120.09 (15)
C24—C23—H23119.8C44—C43—H43120.0
C22—C23—H23119.8C42—C43—H43120.0
C23—C24—C25119.82 (16)C43—C44—C45120.06 (16)
C23—C24—H24120.1C43—C44—H44120.0
C25—C24—H24120.1C45—C44—H44120.0
C26—C25—C24120.18 (17)C46—C45—C44120.17 (17)
C26—C25—H25119.9C46—C45—H45119.9
C24—C25—H25119.9C44—C45—H45119.9
C25—C26—C21120.64 (15)C45—C46—C41120.43 (15)
C25—C26—H26119.7C45—C46—H46119.8
C21—C26—H26119.7C41—C46—H46119.8
C16—N11—C12—C132.2 (2)C36—N31—C32—C331.2 (2)
N11—C12—C13—C140.1 (2)N31—C32—C33—C341.3 (2)
C12—C13—C14—C152.3 (2)C32—C33—C34—C352.6 (2)
C12—C13—C14—C17177.77 (15)C32—C33—C34—C37178.51 (15)
C13—C14—C15—C162.6 (2)C33—C34—C35—C361.5 (2)
C17—C14—C15—C16177.45 (15)C37—C34—C35—C36179.56 (15)
C12—N11—C16—C151.8 (2)C32—N31—C36—C352.4 (2)
C14—C15—C16—N110.5 (3)C34—C35—C36—N311.1 (3)
C13—C14—C17—O1153.73 (16)C33—C34—C37—O3148.38 (16)
C15—C14—C17—O126.2 (2)C35—C34—C37—O330.5 (2)
C13—C14—C17—N1728.4 (2)C33—C34—C37—N3732.1 (2)
C15—C14—C17—N17151.70 (15)C35—C34—C37—N37149.01 (15)
O1—C17—N17—N275.7 (2)O3—C37—N37—N470.7 (2)
C14—C17—N17—N27176.49 (13)C34—C37—N37—N47178.82 (13)
C17—N17—N27—C27179.14 (14)C37—N37—N47—C47173.36 (14)
N17—N27—C27—C21176.42 (13)N37—N47—C47—C41179.05 (13)
N27—C27—C21—C2613.2 (2)N47—C47—C41—C463.2 (2)
N27—C27—C21—C22164.93 (15)N47—C47—C41—C42175.26 (15)
C26—C21—C22—C230.9 (2)C46—C41—C42—C431.6 (2)
C27—C21—C22—C23177.30 (15)C47—C41—C42—C43176.86 (14)
C21—C22—C23—C240.7 (2)C41—C42—C43—C440.6 (3)
C22—C23—C24—C251.6 (2)C42—C43—C44—C451.8 (3)
C23—C24—C25—C260.8 (2)C43—C44—C45—C460.6 (3)
C24—C25—C26—C210.7 (2)C44—C45—C46—C411.6 (2)
C22—C21—C26—C251.6 (2)C42—C41—C46—C452.7 (2)
C27—C21—C26—C25176.53 (15)C47—C41—C46—C45175.71 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N310.882.223.080 (2)166
N37—H37···N11i0.882.223.076 (2)163
C12—H12···Cg1ii0.952.773.517 (2)137
C16—H16···Cg2iii0.952.893.610 (2)134
C26—H26···Cg3iii0.952.993.581 (2)121
C43—H43···Cg4iv0.952.893.610 (2)134
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x, y+1/2, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x, y1/2, z+1/2.
(II) N-isonicotinoyl 2-fluorobenzaldehydehydrazone top
Crystal data top
C13H10FN3OZ = 4
Mr = 243.24F(000) = 504
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4815 (2) ÅCell parameters from 5044 reflections
b = 11.1344 (2) Åθ = 1.5–27.5°
c = 14.5365 (3) ŵ = 0.11 mm1
α = 90.663 (2)°T = 120 K
β = 104.903 (3)°Needle, colourless
γ = 109.268 (2)°0.36 × 0.04 × 0.02 mm
V = 1098.45 (5) Å3
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5044 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3443 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.5°
ϕ & ω scansh = 99
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1414
Tmin = 0.969, Tmax = 0.998l = 1818
24858 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2769P]
where P = (Fo2 + 2Fc2)/3
5044 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C13H10FN3Oγ = 109.268 (2)°
Mr = 243.24V = 1098.45 (5) Å3
Triclinic, P1Z = 4
a = 7.4815 (2) ÅMo Kα radiation
b = 11.1344 (2) ŵ = 0.11 mm1
c = 14.5365 (3) ÅT = 120 K
α = 90.663 (2)°0.36 × 0.04 × 0.02 mm
β = 104.903 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5044 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3443 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.998Rint = 0.058
24858 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.03Δρmax = 0.23 e Å3
5044 reflectionsΔρmin = 0.31 e Å3
325 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.2568 (2)0.10175 (13)0.23246 (9)0.0220 (3)
C120.2461 (3)0.21827 (16)0.22005 (12)0.0229 (4)
C130.2556 (2)0.30368 (15)0.29254 (11)0.0205 (4)
C140.2742 (2)0.26714 (14)0.38461 (11)0.0170 (3)
C150.2839 (3)0.14643 (15)0.39850 (11)0.0220 (4)
C160.2752 (3)0.06825 (16)0.32166 (12)0.0233 (4)
C170.2846 (2)0.34777 (15)0.47089 (11)0.0185 (3)
O10.3187 (2)0.31077 (11)0.55034 (8)0.0287 (3)
N170.2520 (2)0.45985 (12)0.45519 (9)0.0187 (3)
N270.2615 (2)0.53571 (13)0.53311 (9)0.0200 (3)
C270.2206 (2)0.63712 (15)0.51473 (11)0.0209 (4)
C210.2277 (2)0.72362 (15)0.59302 (11)0.0196 (4)
C220.2171 (3)0.84367 (16)0.57814 (12)0.0240 (4)
F220.20023 (18)0.87950 (10)0.48760 (7)0.0388 (3)
C230.2258 (3)0.93012 (16)0.64940 (13)0.0283 (4)
C240.2436 (3)0.89412 (17)0.74086 (13)0.0265 (4)
C250.2523 (3)0.77371 (16)0.75936 (12)0.0252 (4)
C260.2447 (2)0.68958 (15)0.68671 (11)0.0209 (4)
N310.1828 (2)0.59474 (13)0.27155 (10)0.0232 (3)
C320.3068 (2)0.71541 (15)0.28034 (11)0.0211 (4)
C330.3042 (2)0.79405 (15)0.20699 (11)0.0190 (3)
C340.1675 (2)0.74530 (15)0.11893 (11)0.0182 (3)
C350.0398 (2)0.61985 (15)0.10813 (11)0.0205 (4)
C360.0519 (3)0.54914 (16)0.18554 (12)0.0232 (4)
C370.1565 (2)0.81756 (15)0.03206 (11)0.0198 (4)
O30.08845 (19)0.76039 (11)0.04838 (8)0.0289 (3)
N370.2310 (2)0.94722 (12)0.05026 (9)0.0206 (3)
N470.2291 (2)1.01832 (12)0.02739 (9)0.0213 (3)
C470.3226 (2)1.13827 (15)0.00777 (11)0.0203 (4)
C410.3254 (2)1.22065 (15)0.08559 (11)0.0193 (4)
C420.4632 (3)1.34337 (15)0.07278 (11)0.0215 (4)
F420.59329 (15)1.38642 (9)0.01540 (7)0.0303 (3)
C430.4784 (3)1.42250 (16)0.14464 (12)0.0251 (4)
C440.3500 (3)1.37705 (16)0.23482 (12)0.0262 (4)
C450.2069 (3)1.25612 (16)0.25095 (12)0.0246 (4)
C460.1936 (3)1.17945 (16)0.17695 (11)0.0211 (4)
H120.23100.24410.15730.027*
H130.24950.38590.27960.025*
H150.29650.11750.46030.026*
H160.28280.01410.33280.028*
H170.22470.48470.39600.022*
H270.18580.65620.45040.025*
H230.21981.01220.63580.034*
H240.25000.95170.79130.032*
H250.26350.74910.82240.030*
H260.25100.60760.70030.025*
H320.40200.74910.34020.025*
H330.39410.87950.21690.023*
H350.05440.58320.04850.025*
H360.03720.46370.17750.028*
H370.25680.98710.10890.025*
H470.38971.17380.05660.024*
H430.57441.50600.13260.030*
H440.35991.42890.28600.031*
H450.11801.22590.31280.029*
H460.09341.09760.18830.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0218 (8)0.0223 (7)0.0203 (7)0.0065 (6)0.0048 (6)0.0025 (6)
C120.0262 (9)0.0259 (9)0.0178 (8)0.0114 (7)0.0049 (7)0.0011 (6)
C130.0237 (9)0.0203 (8)0.0192 (8)0.0110 (7)0.0043 (7)0.0017 (6)
C140.0153 (8)0.0168 (8)0.0178 (8)0.0050 (6)0.0035 (6)0.0000 (6)
C150.0277 (9)0.0192 (8)0.0187 (8)0.0073 (7)0.0065 (7)0.0015 (6)
C160.0265 (9)0.0178 (8)0.0250 (9)0.0071 (7)0.0068 (7)0.0019 (7)
C170.0182 (8)0.0193 (8)0.0165 (8)0.0055 (7)0.0036 (6)0.0005 (6)
O10.0455 (8)0.0269 (6)0.0167 (6)0.0176 (6)0.0069 (5)0.0029 (5)
N170.0235 (8)0.0179 (7)0.0144 (6)0.0075 (6)0.0042 (5)0.0002 (5)
N270.0214 (7)0.0190 (7)0.0183 (7)0.0053 (6)0.0057 (6)0.0028 (5)
C270.0230 (9)0.0215 (8)0.0182 (8)0.0071 (7)0.0067 (7)0.0020 (6)
C210.0189 (8)0.0184 (8)0.0209 (8)0.0055 (7)0.0059 (7)0.0003 (6)
C220.0267 (9)0.0231 (9)0.0225 (9)0.0084 (7)0.0075 (7)0.0046 (7)
F220.0656 (8)0.0267 (6)0.0310 (6)0.0210 (6)0.0180 (6)0.0113 (4)
C230.0283 (10)0.0184 (8)0.0393 (11)0.0090 (8)0.0102 (8)0.0017 (7)
C240.0205 (9)0.0265 (9)0.0295 (9)0.0052 (7)0.0063 (7)0.0091 (7)
C250.0223 (9)0.0280 (9)0.0216 (9)0.0044 (7)0.0056 (7)0.0043 (7)
C260.0209 (9)0.0200 (8)0.0218 (8)0.0064 (7)0.0067 (7)0.0018 (6)
N310.0299 (8)0.0214 (7)0.0217 (7)0.0114 (6)0.0094 (6)0.0041 (6)
C320.0239 (9)0.0237 (8)0.0173 (8)0.0113 (7)0.0046 (7)0.0008 (6)
C330.0210 (9)0.0168 (8)0.0199 (8)0.0069 (7)0.0066 (7)0.0010 (6)
C340.0218 (9)0.0197 (8)0.0173 (8)0.0107 (7)0.0077 (7)0.0020 (6)
C350.0224 (9)0.0211 (8)0.0183 (8)0.0085 (7)0.0051 (7)0.0002 (6)
C360.0260 (9)0.0193 (8)0.0242 (9)0.0058 (7)0.0096 (7)0.0016 (6)
C370.0229 (9)0.0219 (8)0.0172 (8)0.0102 (7)0.0067 (7)0.0029 (6)
O30.0441 (8)0.0234 (6)0.0164 (6)0.0109 (6)0.0047 (5)0.0003 (5)
N370.0308 (8)0.0185 (7)0.0135 (7)0.0093 (6)0.0064 (6)0.0027 (5)
N470.0285 (8)0.0217 (7)0.0171 (7)0.0115 (6)0.0081 (6)0.0059 (5)
C470.0232 (9)0.0224 (9)0.0172 (8)0.0097 (7)0.0066 (7)0.0013 (6)
C410.0249 (9)0.0188 (8)0.0196 (8)0.0114 (7)0.0100 (7)0.0021 (6)
C420.0244 (9)0.0219 (8)0.0203 (8)0.0102 (7)0.0074 (7)0.0014 (6)
F420.0336 (6)0.0260 (5)0.0246 (5)0.0047 (5)0.0042 (4)0.0031 (4)
C430.0321 (10)0.0172 (8)0.0328 (10)0.0103 (7)0.0180 (8)0.0038 (7)
C440.0386 (11)0.0248 (9)0.0273 (9)0.0193 (8)0.0184 (8)0.0099 (7)
C450.0306 (10)0.0294 (9)0.0203 (8)0.0180 (8)0.0083 (7)0.0050 (7)
C460.0249 (9)0.0204 (8)0.0226 (8)0.0121 (7)0.0087 (7)0.0024 (6)
Geometric parameters (Å, º) top
N11—C121.337 (2)N31—C321.340 (2)
N11—C161.339 (2)N31—C361.345 (2)
C12—C131.383 (2)C32—C331.388 (2)
C12—H120.95C32—H320.95
C13—C141.389 (2)C33—C341.387 (2)
C13—H130.95C33—H330.95
C14—C151.384 (2)C34—C351.388 (2)
C14—C171.504 (2)C34—C371.504 (2)
C15—C161.383 (2)C35—C361.382 (2)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.2238 (19)C37—O31.2225 (19)
C17—N171.359 (2)C37—N371.360 (2)
N17—N271.3779 (19)N37—N471.3859 (17)
N17—H170.8998N37—H370.90
N27—C271.278 (2)N47—C471.275 (2)
C27—C211.461 (2)C47—C411.465 (2)
C27—H270.95C47—H470.95
C21—C221.381 (2)C41—C421.389 (2)
C21—C261.403 (2)C41—C461.400 (2)
C22—F221.3665 (19)C42—F421.3626 (19)
C22—C231.380 (2)C42—C431.377 (2)
C23—C241.379 (3)C43—C441.383 (2)
C23—H230.95C43—H430.95
C24—C251.389 (3)C44—C451.388 (2)
C24—H240.95C44—H440.95
C25—C261.381 (2)C45—C461.384 (2)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
C12—N11—C16116.00 (14)C32—N31—C36116.74 (14)
N11—C12—C13124.35 (15)N31—C32—C33123.75 (15)
N11—C12—H12117.8N31—C32—H32118.1
C13—C12—H12117.8C33—C32—H32118.1
C12—C13—C14118.84 (15)C34—C33—C32118.59 (14)
C12—C13—H13120.6C34—C33—H33120.7
C14—C13—H13120.6C32—C33—H33120.7
C15—C14—C13117.52 (15)C33—C34—C35118.43 (14)
C15—C14—C17116.98 (14)C33—C34—C37123.97 (14)
C13—C14—C17125.50 (14)C35—C34—C37117.50 (14)
C16—C15—C14119.43 (15)C36—C35—C34118.91 (15)
C16—C15—H15120.3C36—C35—H35120.5
C14—C15—H15120.3C34—C35—H35120.5
N11—C16—C15123.85 (15)N31—C36—C35123.57 (15)
N11—C16—H16118.1N31—C36—H36118.2
C15—C16—H16118.1C35—C36—H36118.2
O1—C17—N17123.09 (14)O3—C37—N37123.96 (14)
O1—C17—C14120.08 (14)O3—C37—C34120.59 (14)
N17—C17—C14116.83 (13)N37—C37—C34115.43 (13)
C17—N17—N27117.96 (13)C37—N37—N47117.72 (13)
C17—N17—H17121.8C37—N37—H37122.0
N27—N17—H17120.2N47—N37—H37119.0
C27—N27—N17115.93 (13)C47—N47—N37115.75 (13)
N27—C27—C21119.73 (15)N47—C47—C41119.25 (14)
N27—C27—H27120.1N47—C47—H47120.4
C21—C27—H27120.1C41—C47—H47120.4
C22—C21—C26116.48 (15)C42—C41—C46116.52 (14)
C22—C21—C27121.34 (15)C42—C41—C47121.32 (15)
C26—C21—C27122.18 (15)C46—C41—C47122.14 (15)
F22—C22—C23118.17 (15)F42—C42—C43118.33 (14)
F22—C22—C21117.85 (15)F42—C42—C41117.95 (14)
C23—C22—C21123.97 (16)C43—C42—C41123.71 (15)
C24—C23—C22118.17 (16)C42—C43—C44118.20 (15)
C24—C23—H23120.9C42—C43—H43120.9
C22—C23—H23120.9C44—C43—H43120.9
C23—C24—C25120.11 (16)C43—C44—C45120.37 (15)
C23—C24—H24119.9C43—C44—H44119.8
C25—C24—H24119.9C45—C44—H44119.8
C26—C25—C24120.40 (16)C46—C45—C44120.08 (16)
C26—C25—H25119.8C46—C45—H45120.0
C24—C25—H25119.8C44—C45—H45120.0
C25—C26—C21120.86 (16)C45—C46—C41121.07 (15)
C25—C26—H26119.6C45—C46—H46119.5
C21—C26—H26119.6C41—C46—H46119.5
C16—N11—C12—C130.9 (3)C36—N31—C32—C331.0 (3)
N11—C12—C13—C141.1 (3)N31—C32—C33—C340.8 (3)
C12—C13—C14—C150.5 (2)C32—C33—C34—C350.2 (2)
C12—C13—C14—C17179.41 (15)C32—C33—C34—C37176.37 (16)
C13—C14—C15—C160.1 (2)C33—C34—C35—C360.8 (2)
C17—C14—C15—C16179.94 (15)C37—C34—C35—C36177.30 (15)
C12—N11—C16—C150.2 (2)C32—N31—C36—C350.3 (3)
C14—C15—C16—N110.3 (3)C34—C35—C36—N310.7 (3)
C15—C14—C17—O16.6 (2)C33—C34—C37—O3153.48 (17)
C13—C14—C17—O1173.48 (16)C35—C34—C37—O322.8 (2)
C15—C14—C17—N17172.52 (15)C33—C34—C37—N3724.9 (2)
C13—C14—C17—N177.4 (2)C35—C34—C37—N37158.88 (15)
O1—C17—N17—N271.2 (2)O3—C37—N37—N470.1 (3)
C14—C17—N17—N27179.74 (13)C34—C37—N37—N47178.37 (14)
C17—N17—N27—C27176.75 (14)C37—N37—N47—C47171.32 (15)
N17—N27—C27—C21179.75 (14)N37—N47—C47—C41179.08 (14)
N27—C27—C21—C22169.03 (16)N47—C47—C41—C42163.00 (16)
N27—C27—C21—C2611.2 (3)N47—C47—C41—C4615.4 (3)
C26—C21—C22—F22179.89 (15)C46—C41—C42—F42179.85 (14)
C27—C21—C22—F220.1 (2)C47—C41—C42—F421.6 (2)
C26—C21—C22—C231.2 (3)C46—C41—C42—C431.7 (3)
C27—C21—C22—C23179.05 (16)C47—C41—C42—C43176.82 (16)
F22—C22—C23—C24179.77 (15)F42—C42—C43—C44178.04 (15)
C21—C22—C23—C240.9 (3)C41—C42—C43—C440.4 (3)
C22—C23—C24—C250.0 (3)C42—C43—C44—C451.7 (3)
C23—C24—C25—C260.5 (3)C43—C44—C45—C460.9 (3)
C24—C25—C26—C210.1 (3)C44—C45—C46—C411.3 (3)
C22—C21—C26—C250.7 (2)C42—C41—C46—C452.6 (2)
C27—C21—C26—C25179.58 (16)C47—C41—C46—C45175.96 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N310.902.213.0895 (19)165
N37—H37···N11i0.902.193.0700 (19)165
C13—H13···N310.952.533.463 (2)167
Symmetry code: (i) x, y+1, z.
(III) N-isonicotinoyl 3-fluorobenzaldehydehydrazone top
Crystal data top
C13H10FN3OF(000) = 2016
Mr = 243.24Dx = 1.425 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5207 reflections
a = 13.1910 (4) Åθ = 2.9–27.6°
b = 18.8057 (6) ŵ = 0.11 mm1
c = 18.2843 (4) ÅT = 120 K
V = 4535.7 (2) Å3Needle, colourless
Z = 160.12 × 0.06 × 0.04 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5207 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3977 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 2.9°
ϕ & ω scansh = 1417
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 2421
Tmin = 0.975, Tmax = 0.996l = 2223
32649 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0684P)2 + 1.9661P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
5207 reflectionsΔρmax = 0.67 e Å3
336 parametersΔρmin = 0.66 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0206 (14)
Crystal data top
C13H10FN3OV = 4535.7 (2) Å3
Mr = 243.24Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 13.1910 (4) ŵ = 0.11 mm1
b = 18.8057 (6) ÅT = 120 K
c = 18.2843 (4) Å0.12 × 0.06 × 0.04 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5207 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3977 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.996Rint = 0.071
32649 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.10Δρmax = 0.67 e Å3
5207 reflectionsΔρmin = 0.66 e Å3
336 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N110.48911 (13)0.04000 (9)0.36595 (10)0.0271 (4)
C120.40080 (15)0.00579 (10)0.37487 (11)0.0246 (4)
C130.39033 (14)0.05825 (10)0.41165 (11)0.0233 (4)
C140.47641 (14)0.08952 (10)0.44133 (10)0.0222 (4)
C150.56870 (14)0.05504 (10)0.43207 (11)0.0244 (4)
C160.57108 (15)0.00894 (11)0.39506 (12)0.0266 (4)
C170.47670 (14)0.15832 (10)0.48285 (11)0.0234 (4)
O10.55367 (11)0.19416 (8)0.48815 (8)0.0322 (4)
N170.38765 (12)0.17658 (8)0.51417 (9)0.0237 (4)
N270.38387 (12)0.23581 (8)0.55838 (9)0.0233 (4)
C370.11594 (14)0.11515 (10)0.51004 (11)0.0221 (4)
C270.29804 (14)0.24726 (10)0.58816 (11)0.0236 (4)
C210.28062 (14)0.30477 (10)0.64067 (11)0.0229 (4)
C220.18202 (14)0.31315 (11)0.66708 (11)0.0253 (4)
C230.16399 (14)0.36499 (11)0.71864 (11)0.0256 (4)
F230.06787 (9)0.37216 (7)0.74408 (8)0.0397 (4)
C240.23791 (15)0.40892 (11)0.74548 (11)0.0270 (4)
C250.33552 (15)0.40023 (11)0.71901 (12)0.0274 (5)
C260.35741 (15)0.34884 (11)0.66716 (11)0.0259 (4)
N310.14132 (13)0.02314 (9)0.61911 (10)0.0290 (4)
C320.15375 (16)0.06896 (12)0.56491 (13)0.0327 (5)
C330.07478 (16)0.10133 (12)0.52769 (13)0.0323 (5)
C340.02389 (14)0.08595 (10)0.54775 (11)0.0221 (4)
C350.03770 (16)0.03871 (12)0.60450 (13)0.0342 (5)
C360.04620 (17)0.00940 (13)0.63802 (14)0.0391 (6)
O30.20099 (10)0.09197 (7)0.52349 (8)0.0281 (3)
N370.09777 (12)0.16686 (8)0.46035 (9)0.0240 (4)
N470.17787 (12)0.19446 (9)0.42072 (9)0.0251 (4)
C470.15322 (15)0.24611 (10)0.37845 (11)0.0247 (4)
C410.22817 (15)0.28149 (10)0.33232 (11)0.0257 (4)
C420.32939 (16)0.26093 (12)0.33128 (12)0.0315 (5)
C430.39533 (17)0.29646 (13)0.28605 (13)0.0364 (5)
F430.49092 (15)0.27994 (12)0.28543 (14)0.0521 (8)0.652 (4)
C440.36606 (16)0.35160 (11)0.24134 (12)0.0323 (5)
C450.26565 (17)0.37122 (11)0.24312 (13)0.0334 (5)
F450.2425 (3)0.4250 (2)0.2084 (2)0.0431 (13)0.348 (4)
C460.19610 (16)0.33746 (10)0.28778 (12)0.0273 (4)
H120.34160.02680.35470.029*
H130.32580.08020.41640.028*
H150.62930.07520.45090.029*
H160.63460.03230.38990.032*
H170.33280.15100.50640.028*
H270.24290.21710.57570.028*
H220.12860.28370.64990.030*
H240.22280.44420.78110.032*
H250.38830.43000.73670.033*
H260.42480.34360.64960.031*
H320.22110.08040.55060.039*
H330.08820.13360.48890.039*
H350.10410.02650.62030.041*
H360.03510.02280.67730.047*
H370.03580.18270.45330.029*
H470.08470.26170.37710.030*
H420.35250.22300.36130.038*
H430.46450.28230.28560.044*0.348 (4)
H440.41330.37520.21050.039*
H450.24340.40910.21270.040*0.652 (4)
H460.12720.35220.28820.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0283 (9)0.0255 (8)0.0274 (9)0.0014 (7)0.0046 (7)0.0028 (7)
C120.0237 (10)0.0273 (10)0.0227 (10)0.0017 (8)0.0021 (7)0.0024 (8)
C130.0223 (9)0.0257 (10)0.0218 (10)0.0027 (7)0.0031 (7)0.0007 (8)
C140.0252 (10)0.0233 (9)0.0180 (9)0.0008 (7)0.0036 (7)0.0012 (8)
C150.0229 (10)0.0272 (10)0.0230 (10)0.0014 (8)0.0010 (7)0.0003 (8)
C160.0245 (10)0.0270 (10)0.0284 (11)0.0046 (8)0.0041 (8)0.0006 (9)
C170.0261 (10)0.0235 (9)0.0206 (10)0.0014 (8)0.0013 (7)0.0008 (8)
O10.0282 (8)0.0326 (8)0.0359 (9)0.0075 (6)0.0069 (6)0.0101 (7)
N170.0233 (8)0.0236 (8)0.0242 (9)0.0006 (6)0.0018 (6)0.0046 (7)
N270.0276 (8)0.0219 (8)0.0205 (8)0.0024 (6)0.0002 (6)0.0018 (7)
C370.0223 (9)0.0208 (9)0.0233 (10)0.0015 (7)0.0024 (7)0.0042 (8)
C270.0246 (9)0.0239 (9)0.0222 (10)0.0010 (8)0.0011 (7)0.0008 (8)
C210.0256 (10)0.0236 (9)0.0195 (10)0.0020 (7)0.0026 (7)0.0018 (8)
C220.0231 (10)0.0276 (10)0.0251 (11)0.0007 (8)0.0007 (8)0.0012 (8)
C230.0216 (10)0.0299 (10)0.0252 (10)0.0039 (8)0.0036 (8)0.0006 (9)
F230.0236 (6)0.0493 (8)0.0463 (8)0.0015 (5)0.0092 (5)0.0168 (7)
C240.0315 (11)0.0258 (10)0.0235 (11)0.0030 (8)0.0018 (8)0.0040 (8)
C250.0262 (10)0.0281 (10)0.0280 (11)0.0035 (8)0.0014 (8)0.0054 (9)
C260.0219 (9)0.0290 (10)0.0269 (11)0.0004 (8)0.0047 (8)0.0013 (9)
N310.0247 (9)0.0302 (9)0.0323 (10)0.0033 (7)0.0031 (7)0.0048 (8)
C320.0222 (10)0.0386 (12)0.0371 (12)0.0005 (9)0.0015 (9)0.0102 (10)
C330.0269 (11)0.0369 (11)0.0330 (12)0.0000 (9)0.0022 (9)0.0130 (10)
C340.0231 (10)0.0198 (9)0.0234 (10)0.0013 (7)0.0023 (7)0.0027 (8)
C350.0236 (10)0.0415 (12)0.0374 (13)0.0020 (9)0.0026 (9)0.0116 (10)
C360.0300 (11)0.0462 (13)0.0412 (14)0.0024 (10)0.0000 (10)0.0208 (11)
O30.0221 (7)0.0285 (7)0.0338 (8)0.0000 (6)0.0028 (6)0.0025 (6)
N370.0200 (8)0.0245 (8)0.0276 (9)0.0000 (6)0.0061 (6)0.0018 (7)
N470.0249 (9)0.0257 (8)0.0248 (9)0.0044 (7)0.0075 (7)0.0009 (7)
C470.0252 (10)0.0249 (9)0.0241 (10)0.0025 (8)0.0028 (8)0.0029 (9)
C410.0298 (10)0.0263 (10)0.0211 (10)0.0054 (8)0.0035 (8)0.0038 (8)
C420.0305 (11)0.0342 (11)0.0299 (12)0.0027 (9)0.0043 (8)0.0072 (9)
C430.0298 (11)0.0410 (13)0.0384 (13)0.0034 (9)0.0079 (9)0.0034 (11)
F430.0229 (11)0.0590 (15)0.0746 (18)0.0091 (9)0.0176 (10)0.0325 (13)
C440.0350 (12)0.0296 (11)0.0322 (12)0.0077 (9)0.0104 (9)0.0025 (9)
C450.0416 (13)0.0239 (11)0.0348 (12)0.0039 (9)0.0075 (10)0.0012 (10)
F450.041 (2)0.039 (2)0.050 (3)0.0038 (17)0.0045 (18)0.0235 (19)
C460.0295 (10)0.0239 (10)0.0286 (11)0.0030 (8)0.0036 (8)0.0019 (9)
Geometric parameters (Å, º) top
N11—C161.339 (3)C25—H250.95
N11—C121.341 (2)C26—H260.95
C12—C131.386 (3)N31—C321.323 (3)
C12—H120.95N31—C361.327 (3)
C13—C141.389 (3)C32—C331.385 (3)
C13—H130.95C32—H320.95
C14—C151.390 (3)C33—C341.383 (3)
C14—C171.500 (3)C33—H330.95
C15—C161.381 (3)C34—C351.378 (3)
C15—H150.95C35—C361.380 (3)
C16—H160.95C35—H350.95
C17—O11.223 (2)C36—H360.95
C17—N171.351 (2)N37—N471.382 (2)
N17—N271.377 (2)N37—H370.88
N17—H170.88N47—C471.283 (3)
N27—C271.275 (2)C47—C411.460 (3)
C37—O31.228 (2)C47—H470.95
C37—N371.352 (3)C41—C421.390 (3)
C37—C341.500 (3)C41—C461.396 (3)
C27—C211.464 (3)C42—C431.374 (3)
C27—H270.95C42—H420.95
C21—C261.396 (3)C43—F431.299 (3)
C21—C221.396 (3)C43—C441.376 (3)
C22—C231.377 (3)C43—H430.95
C22—H220.95C44—C451.375 (3)
C23—F231.357 (2)C44—H440.95
C23—C241.369 (3)C45—F451.232 (4)
C24—C251.385 (3)C45—C461.383 (3)
C24—H240.95C45—H450.95
C25—C261.384 (3)C46—H460.95
C16—N11—C12116.36 (17)C21—C26—H26120.0
N11—C12—C13124.22 (18)C32—N31—C36116.05 (18)
N11—C12—H12117.9N31—C32—C33124.1 (2)
C13—C12—H12117.9N31—C32—H32117.9
C12—C13—C14118.42 (17)C33—C32—H32117.9
C12—C13—H13120.8C34—C33—C32119.05 (19)
C14—C13—H13120.8C34—C33—H33120.5
C13—C14—C15118.10 (17)C32—C33—H33120.5
C13—C14—C17124.39 (17)C35—C34—C33117.32 (18)
C15—C14—C17117.51 (17)C35—C34—C37118.36 (17)
C16—C15—C14119.09 (18)C33—C34—C37124.28 (18)
C16—C15—H15120.5C34—C35—C36119.1 (2)
C14—C15—H15120.5C34—C35—H35120.5
N11—C16—C15123.81 (18)C36—C35—H35120.5
N11—C16—H16118.1N31—C36—C35124.4 (2)
C15—C16—H16118.1N31—C36—H36117.8
O1—C17—N17123.25 (18)C35—C36—H36117.8
O1—C17—C14121.18 (17)C37—N37—N47119.12 (16)
N17—C17—C14115.56 (16)C37—N37—H37120.4
C17—N17—N27119.07 (16)N47—N37—H37120.4
C17—N17—H17120.5C47—N47—N37113.97 (16)
N27—N17—H17120.5N47—C47—C41121.42 (18)
C27—N27—N17114.80 (16)N47—C47—H47119.3
O3—C37—N37123.47 (17)C41—C47—H47119.3
O3—C37—C34121.14 (17)C42—C41—C46119.51 (19)
N37—C37—C34115.37 (16)C42—C41—C47122.11 (19)
N27—C27—C21122.97 (18)C46—C41—C47118.38 (18)
N27—C27—H27118.5C43—C42—C41118.8 (2)
C21—C27—H27118.5C43—C42—H42120.6
C26—C21—C22119.28 (18)C41—C42—H42120.6
C26—C21—C27123.52 (17)F43—C43—C42120.2 (2)
C22—C21—C27117.15 (17)F43—C43—C44116.6 (2)
C23—C22—C21118.53 (18)C42—C43—C44123.1 (2)
C23—C22—H22120.7C42—C43—H43118.4
C21—C22—H22120.7C44—C43—H43118.4
F23—C23—C24118.85 (18)C45—C44—C43117.29 (19)
F23—C23—C22117.80 (17)C45—C44—H44121.4
C24—C23—C22123.35 (18)C43—C44—H44121.4
C23—C24—C25117.76 (19)F45—C45—C44116.5 (3)
C23—C24—H24121.1F45—C45—C46121.1 (3)
C25—C24—H24121.1C44—C45—C46122.0 (2)
C26—C25—C24121.03 (19)C44—C45—H45119.0
C26—C25—H25119.5C46—C45—H45119.0
C24—C25—H25119.5C45—C46—C41119.3 (2)
C25—C26—C21120.06 (18)C45—C46—H46120.3
C25—C26—H26120.0C41—C46—H46120.3
C16—N11—C12—C130.0 (3)N31—C32—C33—C340.4 (4)
N11—C12—C13—C140.1 (3)C32—C33—C34—C350.1 (3)
C12—C13—C14—C150.4 (3)C32—C33—C34—C37177.51 (19)
C12—C13—C14—C17179.63 (18)O3—C37—C34—C358.0 (3)
C13—C14—C15—C161.0 (3)N37—C37—C34—C35173.12 (19)
C17—C14—C15—C16179.07 (18)O3—C37—C34—C33169.6 (2)
C12—N11—C16—C150.6 (3)N37—C37—C34—C339.3 (3)
C14—C15—C16—N111.1 (3)C33—C34—C35—C360.1 (3)
C13—C14—C17—O1157.19 (19)C37—C34—C35—C36177.7 (2)
C15—C14—C17—O122.7 (3)C32—N31—C36—C350.9 (4)
C13—C14—C17—N1723.8 (3)C34—C35—C36—N310.5 (4)
C15—C14—C17—N17156.28 (18)O3—C37—N37—N471.8 (3)
O1—C17—N17—N274.5 (3)C34—C37—N37—N47177.11 (16)
C14—C17—N17—N27174.52 (16)C37—N37—N47—C47175.96 (17)
C17—N17—N27—C27177.04 (18)N37—N47—C47—C41179.77 (17)
N17—N27—C27—C21175.89 (17)N47—C47—C41—C420.5 (3)
N27—C27—C21—C265.0 (3)N47—C47—C41—C46179.84 (19)
N27—C27—C21—C22177.60 (19)C46—C41—C42—C430.1 (3)
C26—C21—C22—C230.0 (3)C47—C41—C42—C43179.5 (2)
C27—C21—C22—C23177.53 (18)C41—C42—C43—F43177.9 (2)
C21—C22—C23—F23179.61 (18)C41—C42—C43—C440.1 (4)
C21—C22—C23—C240.0 (3)F43—C43—C44—C45178.0 (2)
F23—C23—C24—C25179.58 (19)C42—C43—C44—C450.2 (4)
C22—C23—C24—C250.0 (3)C43—C44—C45—F45173.0 (3)
C23—C24—C25—C260.0 (3)C43—C44—C45—C460.1 (3)
C24—C25—C26—C210.0 (3)F45—C45—C46—C41173.0 (3)
C22—C21—C26—C250.1 (3)C44—C45—C46—C410.3 (3)
C27—C21—C26—C25177.37 (19)C42—C41—C46—C450.3 (3)
C36—N31—C32—C330.9 (3)C47—C41—C46—C45179.35 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O30.882.092.937 (2)162
N37—H37···N27i0.882.533.381 (2)162
C24—H24···N31ii0.952.593.517 (3)166
C44—H44···N11iii0.952.483.414 (3)167
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x, y+1/2, z+3/2; (iii) x+1, y+1/2, z+1/2.
(IV) N-isonicotinoyl 4-fluorobenzaldehydehydrazone monohydrate top
Crystal data top
C13H10FN3O·H2OF(000) = 544
Mr = 261.26Dx = 1.443 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1630 reflections
a = 6.4189 (3) Åθ = 3.0–27.5°
b = 6.8520 (3) ŵ = 0.11 mm1
c = 27.3451 (12) ÅT = 120 K
V = 1202.70 (9) Å3Block, colourless
Z = 40.48 × 0.38 × 0.22 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
1630 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1412 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 78
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 88
Tmin = 0.960, Tmax = 0.976l = 3534
8595 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.050P)2 + 0.2601P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1630 reflectionsΔρmax = 0.21 e Å3
176 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Friedel pairs merged
Primary atom site location: structure-invariant direct methods
Crystal data top
C13H10FN3O·H2OV = 1202.70 (9) Å3
Mr = 261.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.4189 (3) ŵ = 0.11 mm1
b = 6.8520 (3) ÅT = 120 K
c = 27.3451 (12) Å0.48 × 0.38 × 0.22 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
1630 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1412 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.976Rint = 0.031
8595 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.088H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
1630 reflectionsΔρmin = 0.20 e Å3
176 parametersAbsolute structure: Friedel pairs merged
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.1309 (3)0.1955 (2)0.79927 (6)0.0226 (4)
C120.0466 (3)0.1661 (3)0.75506 (7)0.0208 (4)
C130.1535 (3)0.1943 (3)0.71156 (7)0.0192 (4)
C140.3602 (3)0.2524 (3)0.71330 (7)0.0177 (4)
C150.4512 (3)0.2827 (3)0.75919 (7)0.0214 (4)
C160.3300 (3)0.2539 (3)0.80056 (7)0.0237 (4)
C170.4957 (3)0.2774 (3)0.66882 (6)0.0185 (4)
O10.6837 (2)0.2441 (2)0.67050 (5)0.0246 (3)
N170.3945 (2)0.3369 (2)0.62815 (6)0.0195 (4)
N270.5123 (2)0.3767 (2)0.58669 (5)0.0196 (3)
C270.4069 (3)0.4085 (3)0.54793 (7)0.0196 (4)
C210.5097 (3)0.4644 (3)0.50215 (7)0.0183 (4)
C220.3966 (3)0.4563 (3)0.45859 (7)0.0205 (4)
C230.4844 (3)0.5159 (3)0.41463 (7)0.0225 (4)
C240.6858 (3)0.5828 (3)0.41546 (7)0.0214 (4)
F240.77439 (19)0.64424 (19)0.37277 (4)0.0309 (3)
C250.8048 (3)0.5928 (3)0.45748 (7)0.0214 (4)
C260.7147 (3)0.5337 (3)0.50133 (7)0.0198 (4)
O20.0118 (2)0.4809 (2)0.61671 (5)0.0221 (3)
H120.09410.12380.75340.025*
H130.08610.17400.68100.023*
H150.59270.32200.76190.026*
H160.39170.27690.83160.028*
H170.25850.36890.62880.023*
H270.25950.39580.54880.024*
H220.25740.40930.45900.025*
H230.40750.51050.38500.027*
H250.94430.63870.45650.026*
H260.79260.54040.53080.024*
H2A0.02940.56130.63950.033*
H2B0.11750.40870.61600.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0230 (8)0.0242 (9)0.0205 (8)0.0013 (7)0.0018 (7)0.0027 (7)
C120.0166 (9)0.0221 (9)0.0236 (9)0.0007 (8)0.0003 (8)0.0029 (8)
C130.0184 (9)0.0207 (9)0.0186 (9)0.0006 (8)0.0021 (7)0.0005 (8)
C140.0189 (9)0.0156 (8)0.0187 (9)0.0005 (8)0.0006 (7)0.0016 (8)
C150.0194 (9)0.0214 (9)0.0234 (9)0.0010 (8)0.0026 (8)0.0006 (8)
C160.0242 (10)0.0271 (10)0.0197 (9)0.0001 (10)0.0028 (8)0.0009 (8)
C170.0161 (9)0.0191 (9)0.0203 (9)0.0006 (8)0.0018 (7)0.0008 (7)
O10.0150 (6)0.0338 (8)0.0250 (7)0.0008 (7)0.0012 (5)0.0045 (6)
N170.0156 (7)0.0253 (9)0.0176 (8)0.0006 (7)0.0038 (6)0.0022 (7)
N270.0197 (8)0.0215 (8)0.0175 (7)0.0001 (7)0.0051 (6)0.0002 (6)
C270.0164 (8)0.0213 (9)0.0211 (9)0.0011 (8)0.0033 (8)0.0001 (8)
C210.0189 (8)0.0159 (8)0.0200 (9)0.0021 (8)0.0029 (8)0.0007 (7)
C220.0175 (9)0.0210 (9)0.0230 (9)0.0005 (8)0.0015 (8)0.0016 (8)
C230.0234 (9)0.0242 (10)0.0199 (9)0.0007 (9)0.0007 (8)0.0016 (8)
C240.0262 (9)0.0190 (9)0.0188 (9)0.0026 (8)0.0077 (8)0.0006 (8)
F240.0340 (7)0.0364 (7)0.0222 (6)0.0026 (6)0.0090 (5)0.0056 (5)
C250.0187 (9)0.0182 (9)0.0274 (10)0.0020 (8)0.0029 (8)0.0016 (8)
C260.0199 (9)0.0177 (9)0.0217 (9)0.0002 (8)0.0017 (8)0.0021 (8)
O20.0178 (6)0.0260 (7)0.0224 (7)0.0012 (6)0.0031 (5)0.0031 (6)
Geometric parameters (Å, º) top
N11—C121.339 (2)C27—C211.466 (2)
N11—C161.340 (3)C27—H270.95
C12—C131.387 (3)C21—C221.396 (2)
C12—H120.95C21—C261.399 (3)
C13—C141.386 (3)C22—C231.389 (3)
C13—H130.95C22—H220.95
C14—C151.400 (3)C23—C241.372 (3)
C14—C171.505 (2)C23—H230.95
C15—C161.387 (3)C24—F241.365 (2)
C15—H150.95C24—C251.381 (3)
C16—H160.95C25—C261.392 (3)
C17—O11.229 (2)C25—H250.95
C17—N171.351 (2)C26—H260.95
N17—N271.390 (2)O2—H2A0.84
N17—H170.90O2—H2B0.84
N27—C271.276 (2)
C12—N11—C16116.98 (17)N27—C27—C21120.99 (17)
N11—C12—C13123.62 (17)N27—C27—H27119.5
N11—C12—H12118.2C21—C27—H27119.5
C13—C12—H12118.2C22—C21—C26119.27 (17)
C14—C13—C12118.95 (18)C22—C21—C27118.95 (17)
C14—C13—H13120.5C26—C21—C27121.71 (17)
C12—C13—H13120.5C23—C22—C21121.06 (18)
C13—C14—C15118.23 (17)C23—C22—H22119.5
C13—C14—C17123.93 (17)C21—C22—H22119.5
C15—C14—C17117.79 (16)C24—C23—C22117.78 (18)
C16—C15—C14118.41 (17)C24—C23—H23121.1
C16—C15—H15120.8C22—C23—H23121.1
C14—C15—H15120.8F24—C24—C23118.77 (18)
N11—C16—C15123.79 (18)F24—C24—C25117.79 (17)
N11—C16—H16118.1C23—C24—C25123.44 (18)
C15—C16—H16118.1C24—C25—C26118.23 (18)
O1—C17—N17123.98 (17)C24—C25—H25120.9
O1—C17—C14121.07 (17)C26—C25—H25120.9
N17—C17—C14114.95 (15)C25—C26—C21120.22 (17)
C17—N17—N27117.96 (15)C25—C26—H26119.9
C17—N17—H17121.5C21—C26—H26119.9
N27—N17—H17119.8H2A—O2—H2B107.2
C27—N27—N17114.97 (15)
C16—N11—C12—C130.5 (3)C17—N17—N27—C27171.65 (17)
N11—C12—C13—C141.3 (3)N17—N27—C27—C21176.14 (16)
C12—C13—C14—C150.8 (3)N27—C27—C21—C22166.14 (18)
C12—C13—C14—C17176.66 (17)N27—C27—C21—C2616.8 (3)
C13—C14—C15—C160.3 (3)C26—C21—C22—C230.0 (3)
C17—C14—C15—C16177.91 (18)C27—C21—C22—C23177.15 (18)
C12—N11—C16—C150.8 (3)C21—C22—C23—C240.0 (3)
C14—C15—C16—N111.1 (3)C22—C23—C24—F24179.26 (18)
C13—C14—C17—O1147.6 (2)C22—C23—C24—C250.3 (3)
C15—C14—C17—O129.9 (3)F24—C24—C25—C26178.91 (17)
C13—C14—C17—N1732.1 (3)C23—C24—C25—C260.7 (3)
C15—C14—C17—N17150.38 (18)C24—C25—C26—C210.7 (3)
O1—C17—N17—N274.9 (3)C22—C21—C26—C250.3 (3)
C14—C17—N17—N27175.40 (15)C27—C21—C26—C25177.43 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O20.901.932.8059 (18)165
O2—H2A···N11i0.842.022.833 (2)163
O2—H2B···O1ii0.842.262.9354 (19)137
O2—H2B···N27ii0.842.523.2427 (18)145
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x1, y, z.
(V) N-isonicotinoyl 2-chlorobenzaldehydehydrazone top
Crystal data top
C13H10ClN3OF(000) = 536
Mr = 259.69Dx = 1.440 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2757 reflections
a = 7.9977 (2) Åθ = 3.5–27.5°
b = 6.7184 (2) ŵ = 0.31 mm1
c = 22.5514 (6) ÅT = 120 K
β = 98.609 (3)°Plate, colourless
V = 1198.07 (6) Å30.40 × 0.14 × 0.02 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2757 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2159 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.5°
ϕ & ω scansh = 1010
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 78
Tmin = 0.893, Tmax = 0.994l = 2929
18325 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.4843P]
where P = (Fo2 + 2Fc2)/3
2757 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C13H10ClN3OV = 1198.07 (6) Å3
Mr = 259.69Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9977 (2) ŵ = 0.31 mm1
b = 6.7184 (2) ÅT = 120 K
c = 22.5514 (6) Å0.40 × 0.14 × 0.02 mm
β = 98.609 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2757 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2159 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.994Rint = 0.042
18325 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å3
2757 reflectionsΔρmin = 0.29 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.07515 (16)0.1695 (2)0.67399 (6)0.0214 (3)
C120.01389 (19)0.3068 (2)0.64910 (7)0.0208 (3)
C130.18814 (19)0.3082 (2)0.65489 (7)0.0192 (3)
C140.27868 (18)0.1597 (2)0.68869 (6)0.0161 (3)
C150.18877 (19)0.0168 (2)0.71512 (7)0.0201 (3)
C160.01336 (19)0.0271 (3)0.70645 (7)0.0227 (4)
C170.46874 (18)0.1534 (2)0.70072 (7)0.0157 (3)
O10.54326 (13)0.10882 (17)0.75062 (5)0.0211 (3)
N170.55609 (15)0.19946 (19)0.65557 (5)0.0161 (3)
N270.47650 (16)0.21267 (19)0.59726 (5)0.0165 (3)
C270.57369 (18)0.2355 (2)0.55758 (7)0.0170 (3)
C210.5007 (2)0.2480 (2)0.49427 (7)0.0165 (3)
C220.60118 (19)0.2658 (2)0.44858 (7)0.0181 (3)
Cl220.82143 (5)0.27586 (7)0.466582 (18)0.02905 (14)
C230.5319 (2)0.2757 (2)0.38862 (7)0.0212 (3)
C240.3585 (2)0.2667 (2)0.37239 (7)0.0225 (3)
C250.2548 (2)0.2456 (2)0.41642 (7)0.0223 (3)
C260.32502 (19)0.2373 (2)0.47628 (7)0.0192 (3)
H120.04650.40940.62610.025*
H130.24530.40870.63610.023*
H150.24620.08640.73880.024*
H160.04710.07210.72450.027*
H170.66660.18490.66310.019*
H270.69260.24420.56920.020*
H230.60330.28870.35870.025*
H240.31010.27490.33130.027*
H250.13570.23690.40530.027*
H260.25280.22410.50590.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0143 (6)0.0298 (8)0.0202 (7)0.0003 (5)0.0023 (5)0.0005 (6)
C120.0175 (8)0.0230 (8)0.0218 (8)0.0032 (6)0.0024 (6)0.0018 (6)
C130.0161 (7)0.0206 (8)0.0214 (8)0.0010 (6)0.0047 (6)0.0007 (6)
C140.0146 (7)0.0210 (8)0.0130 (7)0.0005 (6)0.0023 (6)0.0027 (6)
C150.0167 (8)0.0253 (8)0.0177 (8)0.0000 (6)0.0004 (6)0.0039 (6)
C160.0170 (8)0.0309 (9)0.0203 (8)0.0052 (6)0.0032 (6)0.0033 (7)
C170.0146 (7)0.0154 (7)0.0173 (8)0.0001 (6)0.0030 (6)0.0014 (6)
O10.0176 (6)0.0291 (6)0.0157 (5)0.0001 (5)0.0007 (4)0.0026 (5)
N170.0095 (6)0.0237 (7)0.0145 (6)0.0000 (5)0.0002 (5)0.0007 (5)
N270.0169 (6)0.0196 (6)0.0128 (6)0.0008 (5)0.0011 (5)0.0000 (5)
C270.0153 (7)0.0180 (8)0.0180 (8)0.0004 (6)0.0033 (6)0.0007 (6)
C210.0198 (7)0.0138 (7)0.0164 (8)0.0000 (6)0.0039 (6)0.0003 (6)
C220.0194 (7)0.0164 (8)0.0192 (8)0.0015 (6)0.0052 (6)0.0000 (6)
Cl220.0196 (2)0.0445 (3)0.0246 (2)0.00346 (17)0.00826 (16)0.00145 (18)
C230.0302 (9)0.0169 (8)0.0181 (8)0.0021 (6)0.0088 (7)0.0003 (6)
C240.0313 (9)0.0199 (8)0.0155 (8)0.0003 (7)0.0002 (7)0.0004 (6)
C250.0212 (8)0.0242 (8)0.0203 (8)0.0027 (7)0.0013 (6)0.0003 (6)
C260.0196 (7)0.0203 (8)0.0181 (8)0.0020 (6)0.0040 (6)0.0004 (6)
Geometric parameters (Å, º) top
N11—C121.339 (2)N27—C271.2793 (19)
N11—C161.341 (2)C27—C211.462 (2)
C12—C131.380 (2)C27—H270.95
C12—H120.95C21—C221.403 (2)
C13—C141.391 (2)C21—C261.405 (2)
C13—H130.95C22—C231.384 (2)
C14—C151.386 (2)C22—Cl221.7488 (16)
C14—C171.504 (2)C23—C241.382 (2)
C15—C161.389 (2)C23—H230.95
C15—H150.95C24—C251.393 (2)
C16—H160.95C24—H240.95
C17—O11.2291 (18)C25—C261.383 (2)
C17—N171.3538 (19)C25—H250.95
N17—N271.3755 (17)C26—H260.95
N17—H170.88
C12—N11—C16116.74 (13)C27—N27—N17115.71 (12)
N11—C12—C13123.91 (15)N27—C27—C21119.64 (13)
N11—C12—H12118.0N27—C27—H27120.2
C13—C12—H12118.0C21—C27—H27120.2
C12—C13—C14118.85 (14)C22—C21—C26116.75 (14)
C12—C13—H13120.6C22—C21—C27122.24 (14)
C14—C13—H13120.6C26—C21—C27121.00 (13)
C15—C14—C13118.10 (14)C23—C22—C21122.15 (14)
C15—C14—C17118.57 (13)C23—C22—Cl22117.83 (12)
C13—C14—C17123.24 (13)C21—C22—Cl22120.02 (12)
C14—C15—C16118.89 (15)C24—C23—C22119.71 (14)
C14—C15—H15120.6C24—C23—H23120.1
C16—C15—H15120.6C22—C23—H23120.1
N11—C16—C15123.51 (15)C23—C24—C25119.77 (15)
N11—C16—H16118.2C23—C24—H24120.1
C15—C16—H16118.2C25—C24—H24120.1
O1—C17—N17120.67 (13)C26—C25—C24120.13 (15)
O1—C17—C14120.69 (13)C26—C25—H25119.9
N17—C17—C14118.64 (13)C24—C25—H25119.9
C17—N17—N27121.11 (12)C25—C26—C21121.47 (14)
C17—N17—H17116.5C25—C26—H26119.3
N27—N17—H17120.0C21—C26—H26119.3
C16—N11—C12—C130.3 (2)N17—N27—C27—C21179.08 (12)
N11—C12—C13—C140.3 (2)N27—C27—C21—C22177.67 (14)
C12—C13—C14—C150.0 (2)N27—C27—C21—C260.6 (2)
C12—C13—C14—C17176.53 (14)C26—C21—C22—C231.0 (2)
C13—C14—C15—C160.4 (2)C27—C21—C22—C23179.38 (14)
C17—C14—C15—C16177.09 (14)C26—C21—C22—Cl22178.92 (11)
C12—N11—C16—C150.1 (2)C27—C21—C22—Cl220.6 (2)
C14—C15—C16—N110.5 (2)C21—C22—C23—C240.4 (2)
C15—C14—C17—O138.0 (2)Cl22—C22—C23—C24179.49 (12)
C13—C14—C17—O1138.45 (16)C22—C23—C24—C250.7 (2)
C15—C14—C17—N17142.48 (15)C23—C24—C25—C261.2 (2)
C13—C14—C17—N1741.0 (2)C24—C25—C26—C210.6 (2)
O1—C17—N17—N27167.57 (13)C22—C21—C26—C250.5 (2)
C14—C17—N17—N2712.9 (2)C27—C21—C26—C25178.89 (14)
C17—N17—N27—C27172.66 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.882.052.923 (2)175
C23—H23···O1ii0.952.513.222 (2)132
C16—H16···Cg3iii0.952.953.723 (2)154
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x, y+3/2, z+3/2.
(VI) N-isonicotinoyl 3-chlorobenzaldehydehydrazone top
Crystal data top
C13H10ClN3OF(000) = 536
Mr = 259.69Dx = 1.467 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2691 reflections
a = 7.4524 (3) Åθ = 2.3–27.5°
b = 11.2367 (4) ŵ = 0.32 mm1
c = 14.3949 (3) ÅT = 120 K
β = 102.701 (2)°Block, colourless
V = 1175.94 (7) Å30.34 × 0.28 × 0.18 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2691 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2076 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.3°
ϕ & ω scansh = 89
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1414
Tmin = 0.886, Tmax = 0.946l = 1518
15675 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0972P)2 + 0.0157P]
where P = (Fo2 + 2Fc2)/3
2691 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C13H10ClN3OV = 1175.94 (7) Å3
Mr = 259.69Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4524 (3) ŵ = 0.32 mm1
b = 11.2367 (4) ÅT = 120 K
c = 14.3949 (3) Å0.34 × 0.28 × 0.18 mm
β = 102.701 (2)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2691 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2076 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.946Rint = 0.034
15675 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.08Δρmax = 0.38 e Å3
2691 reflectionsΔρmin = 0.33 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.33989 (19)0.02209 (12)0.21775 (9)0.0201 (3)
C120.2546 (2)0.12766 (15)0.21030 (11)0.0205 (4)
C130.2716 (2)0.20830 (14)0.28515 (10)0.0189 (3)
C140.3828 (2)0.17859 (13)0.37300 (10)0.0173 (3)
C150.4760 (2)0.07098 (15)0.38044 (10)0.0193 (4)
C160.4504 (2)0.00387 (15)0.30272 (11)0.0212 (4)
C170.4036 (2)0.25233 (14)0.46237 (10)0.0192 (4)
O10.49112 (18)0.21469 (11)0.53817 (7)0.0310 (3)
N170.31632 (18)0.36002 (12)0.45326 (8)0.0185 (3)
N270.32877 (19)0.42603 (12)0.53490 (9)0.0187 (3)
C270.2404 (2)0.52468 (14)0.52636 (10)0.0183 (3)
C210.2506 (2)0.60117 (14)0.61006 (10)0.0181 (3)
C220.3610 (2)0.57045 (14)0.69811 (10)0.0194 (4)
C230.3677 (2)0.64497 (16)0.77489 (11)0.0226 (4)
Cl230.50652 (7)0.60557 (4)0.88451 (3)0.0389 (2)
C240.2685 (2)0.75100 (15)0.76697 (12)0.0251 (4)
C250.1614 (2)0.78112 (15)0.67912 (12)0.0257 (4)
C260.1511 (2)0.70700 (15)0.60082 (11)0.0226 (4)
H120.17830.14870.15060.025*
H130.20840.28230.27640.023*
H150.55690.04900.43860.023*
H160.51400.07770.30940.025*
H170.25490.38600.39760.022*
H270.16860.54820.46620.022*
H220.43080.49900.70510.023*
H240.27450.80130.82060.030*
H250.09380.85350.67210.031*
H260.07610.72860.54090.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0232 (7)0.0182 (7)0.0181 (6)0.0010 (6)0.0028 (5)0.0022 (5)
C120.0263 (9)0.0192 (8)0.0146 (7)0.0017 (7)0.0012 (6)0.0001 (6)
C130.0228 (8)0.0148 (8)0.0179 (7)0.0016 (6)0.0023 (6)0.0011 (6)
C140.0201 (8)0.0157 (8)0.0160 (7)0.0037 (6)0.0037 (6)0.0006 (6)
C150.0215 (8)0.0193 (8)0.0160 (7)0.0002 (6)0.0014 (6)0.0006 (6)
C160.0221 (8)0.0186 (8)0.0220 (8)0.0025 (6)0.0032 (6)0.0005 (6)
C170.0239 (9)0.0169 (8)0.0156 (7)0.0016 (6)0.0021 (6)0.0003 (6)
O10.0481 (8)0.0226 (7)0.0172 (6)0.0079 (6)0.0038 (5)0.0019 (5)
N170.0259 (7)0.0164 (7)0.0121 (6)0.0002 (6)0.0019 (5)0.0021 (5)
N270.0252 (7)0.0178 (7)0.0131 (6)0.0024 (6)0.0043 (5)0.0022 (5)
C270.0214 (8)0.0180 (8)0.0160 (7)0.0008 (6)0.0053 (6)0.0003 (6)
C210.0210 (8)0.0170 (8)0.0175 (8)0.0031 (6)0.0068 (6)0.0007 (6)
C220.0231 (8)0.0156 (8)0.0198 (8)0.0016 (6)0.0057 (6)0.0018 (6)
C230.0279 (9)0.0217 (9)0.0185 (8)0.0061 (7)0.0056 (6)0.0029 (6)
Cl230.0563 (4)0.0348 (3)0.0196 (3)0.0020 (2)0.0046 (2)0.00640 (17)
C240.0332 (10)0.0193 (9)0.0259 (8)0.0046 (7)0.0130 (7)0.0076 (6)
C250.0316 (10)0.0165 (8)0.0321 (9)0.0015 (7)0.0141 (7)0.0015 (7)
C260.0252 (9)0.0202 (9)0.0232 (8)0.0005 (7)0.0067 (6)0.0014 (6)
Geometric parameters (Å, º) top
N11—C121.339 (2)N27—C271.281 (2)
N11—C161.348 (2)C27—C211.468 (2)
C12—C131.392 (2)C27—H270.95
C12—H120.95C21—C261.392 (2)
C13—C141.392 (2)C21—C221.394 (2)
C13—H130.95C22—C231.379 (2)
C14—C151.387 (2)C22—H220.95
C14—C171.509 (2)C23—C241.394 (3)
C15—C161.379 (2)C23—Cl231.7429 (17)
C15—H150.95C24—C251.381 (2)
C16—H160.95C24—H240.95
C17—O11.2172 (18)C25—C261.390 (2)
C17—N171.366 (2)C25—H250.95
N17—N271.3755 (17)C26—H260.95
N17—H170.88
C12—N11—C16116.68 (13)C27—N27—N17116.61 (13)
N11—C12—C13123.64 (14)N27—C27—C21119.67 (14)
N11—C12—H12118.2N27—C27—H27120.2
C13—C12—H12118.2C21—C27—H27120.2
C14—C13—C12118.81 (15)C26—C21—C22119.59 (14)
C14—C13—H13120.6C26—C21—C27119.42 (14)
C12—C13—H13120.6C22—C21—C27120.98 (14)
C15—C14—C13117.86 (14)C23—C22—C21119.25 (15)
C15—C14—C17117.19 (13)C23—C22—H22120.4
C13—C14—C17124.90 (14)C21—C22—H22120.4
C16—C15—C14119.43 (14)C22—C23—C24121.90 (15)
C16—C15—H15120.3C22—C23—Cl23118.77 (14)
C14—C15—H15120.3C24—C23—Cl23119.33 (12)
N11—C16—C15123.54 (15)C25—C24—C23118.30 (15)
N11—C16—H16118.2C25—C24—H24120.9
C15—C16—H16118.2C23—C24—H24120.9
O1—C17—N17122.93 (14)C24—C25—C26120.89 (16)
O1—C17—C14120.52 (14)C24—C25—H25119.6
N17—C17—C14116.53 (12)C26—C25—H25119.6
C17—N17—N27117.02 (12)C25—C26—C21120.07 (15)
C17—N17—H17121.5C25—C26—H26120.0
N27—N17—H17121.5C21—C26—H26120.0
C16—N11—C12—C131.4 (2)C17—N17—N27—C27177.27 (14)
N11—C12—C13—C140.1 (2)N17—N27—C27—C21178.64 (13)
C12—C13—C14—C152.0 (2)N27—C27—C21—C26178.61 (15)
C12—C13—C14—C17175.23 (14)N27—C27—C21—C222.6 (2)
C13—C14—C15—C162.4 (2)C26—C21—C22—C230.8 (2)
C17—C14—C15—C16175.05 (14)C27—C21—C22—C23179.62 (14)
C12—N11—C16—C151.0 (2)C21—C22—C23—C240.6 (2)
C14—C15—C16—N110.9 (2)C21—C22—C23—Cl23179.93 (12)
C15—C14—C17—O13.8 (2)C22—C23—C24—C250.2 (3)
C13—C14—C17—O1173.48 (15)Cl23—C23—C24—C25179.17 (13)
C15—C14—C17—N17177.74 (14)C23—C24—C25—C260.7 (3)
C13—C14—C17—N175.0 (2)C24—C25—C26—C210.5 (3)
O1—C17—N17—N270.8 (2)C22—C21—C26—C250.3 (2)
C14—C17—N17—N27177.67 (13)C27—C21—C26—C25179.11 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.882.253.0776 (18)156
C12—H12···O1ii0.952.433.316 (2)154
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.
(VIII) N-isonicotinoyl 2-bromobenzaldehydehydrazone top
Crystal data top
C13H10BrN3OF(000) = 608
Mr = 304.15Dx = 1.688 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2746 reflections
a = 8.0268 (2) Åθ = 3.2–27.7°
b = 6.7134 (3) ŵ = 3.43 mm1
c = 22.5024 (10) ÅT = 120 K
β = 99.297 (3)°Lath, colourless
V = 1196.66 (8) Å30.12 × 0.03 × 0.02 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2746 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2182 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 9.091 pixels mm-1θmax = 27.7°, θmin = 3.2°
ϕ & ω scansh = 910
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 88
Tmin = 0.654, Tmax = 0.935l = 2929
11911 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0225P)2 + 1.7209P]
where P = (Fo2 + 2Fc2)/3
2746 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
C13H10BrN3OV = 1196.66 (8) Å3
Mr = 304.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0268 (2) ŵ = 3.43 mm1
b = 6.7134 (3) ÅT = 120 K
c = 22.5024 (10) Å0.12 × 0.03 × 0.02 mm
β = 99.297 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2746 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2182 reflections with I > 2σ(I)
Tmin = 0.654, Tmax = 0.935Rint = 0.062
11911 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.06Δρmax = 0.45 e Å3
2746 reflectionsΔρmin = 0.58 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.0743 (3)0.1663 (4)0.67403 (12)0.0203 (6)
C120.0136 (4)0.3048 (5)0.64913 (14)0.0200 (6)
C130.1868 (4)0.3046 (5)0.65474 (14)0.0179 (6)
C140.2776 (3)0.1554 (4)0.68826 (13)0.0151 (6)
C150.1892 (4)0.0128 (5)0.71467 (14)0.0184 (6)
C160.0146 (4)0.0233 (5)0.70585 (14)0.0218 (7)
C170.4682 (3)0.1487 (4)0.70088 (13)0.0150 (6)
O10.5423 (2)0.1039 (3)0.75071 (9)0.0197 (5)
N170.5537 (3)0.1969 (4)0.65575 (11)0.0150 (5)
N270.4743 (3)0.2120 (4)0.59707 (11)0.0147 (5)
C270.5722 (4)0.2340 (4)0.55812 (13)0.0156 (6)
C210.5022 (4)0.2478 (4)0.49409 (13)0.0144 (6)
C220.6039 (4)0.2648 (4)0.44941 (14)0.0169 (6)
Br220.84348 (4)0.27171 (5)0.470142 (14)0.02685 (13)
C230.5372 (4)0.2772 (4)0.38870 (14)0.0188 (6)
C240.3636 (4)0.2694 (4)0.37134 (14)0.0210 (7)
C250.2599 (4)0.2477 (4)0.41460 (14)0.0198 (7)
C260.3274 (4)0.2390 (4)0.47474 (14)0.0183 (6)
H120.04720.40850.62640.024*
H130.24340.40510.63600.022*
H150.24710.09060.73840.022*
H160.04510.07710.72350.026*
H170.67310.17580.65970.018*
H270.69080.24150.57080.019*
H230.60950.29080.35940.023*
H240.31580.27880.33000.025*
H250.14110.23880.40260.024*
H260.25410.22680.50370.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0126 (12)0.0304 (16)0.0181 (14)0.0005 (10)0.0025 (10)0.0026 (12)
C120.0218 (15)0.0204 (17)0.0175 (16)0.0015 (12)0.0019 (12)0.0008 (13)
C130.0179 (14)0.0189 (16)0.0176 (16)0.0013 (11)0.0049 (12)0.0009 (12)
C140.0154 (14)0.0188 (16)0.0119 (15)0.0009 (11)0.0042 (11)0.0031 (12)
C150.0176 (14)0.0239 (17)0.0140 (16)0.0014 (12)0.0034 (11)0.0031 (13)
C160.0207 (15)0.0273 (18)0.0171 (17)0.0055 (12)0.0027 (12)0.0049 (13)
C170.0164 (14)0.0168 (16)0.0115 (15)0.0017 (11)0.0018 (11)0.0021 (12)
O10.0188 (11)0.0278 (13)0.0116 (11)0.0014 (9)0.0003 (8)0.0033 (9)
N170.0117 (11)0.0225 (14)0.0107 (13)0.0005 (9)0.0015 (9)0.0012 (10)
N270.0141 (11)0.0190 (13)0.0107 (12)0.0003 (9)0.0017 (9)0.0015 (10)
C270.0163 (14)0.0154 (15)0.0145 (15)0.0005 (11)0.0004 (11)0.0022 (12)
C210.0179 (14)0.0142 (15)0.0112 (14)0.0012 (10)0.0028 (11)0.0011 (11)
C220.0173 (14)0.0153 (15)0.0185 (16)0.0017 (11)0.0042 (11)0.0000 (12)
Br220.01710 (18)0.0442 (2)0.02051 (19)0.00275 (13)0.00674 (12)0.00206 (15)
C230.0277 (16)0.0138 (15)0.0165 (16)0.0024 (12)0.0087 (12)0.0008 (12)
C240.0288 (17)0.0207 (17)0.0131 (16)0.0003 (13)0.0021 (12)0.0013 (13)
C250.0192 (15)0.0207 (17)0.0183 (16)0.0039 (12)0.0005 (12)0.0002 (13)
C260.0180 (15)0.0194 (16)0.0181 (16)0.0004 (11)0.0045 (12)0.0016 (13)
Geometric parameters (Å, º) top
N11—C161.334 (4)N27—C271.276 (4)
N11—C121.343 (4)C27—C211.462 (4)
C12—C131.375 (4)C27—H270.95
C12—H120.95C21—C221.398 (4)
C13—C141.388 (4)C21—C261.402 (4)
C13—H130.95C22—C231.387 (4)
C14—C151.382 (4)C22—Br221.905 (3)
C14—C171.511 (4)C23—C241.386 (4)
C15—C161.385 (4)C23—H230.95
C15—H150.95C24—C251.387 (4)
C16—H160.95C24—H240.95
C17—O11.219 (3)C25—C261.375 (4)
C17—N171.353 (4)C25—H250.95
N17—N271.374 (3)C26—H260.95
N17—H170.9588
C16—N11—C12116.8 (3)C27—N27—N17115.3 (2)
N11—C12—C13123.5 (3)N27—C27—C21120.2 (3)
N11—C12—H12118.2N27—C27—H27119.9
C13—C12—H12118.2C21—C27—H27119.9
C12—C13—C14119.0 (3)C22—C21—C26116.8 (3)
C12—C13—H13120.5C22—C21—C27122.5 (3)
C14—C13—H13120.5C26—C21—C27120.6 (3)
C15—C14—C13118.2 (3)C23—C22—C21122.4 (3)
C15—C14—C17118.2 (3)C23—C22—Br22117.0 (2)
C13—C14—C17123.4 (3)C21—C22—Br22120.6 (2)
C14—C15—C16118.8 (3)C24—C23—C22119.1 (3)
C14—C15—H15120.6C24—C23—H23120.5
C16—C15—H15120.6C22—C23—H23120.5
N11—C16—C15123.7 (3)C23—C24—C25119.7 (3)
N11—C16—H16118.1C23—C24—H24120.1
C15—C16—H16118.1C25—C24—H24120.1
O1—C17—N17121.2 (2)C26—C25—C24120.6 (3)
O1—C17—C14120.6 (3)C26—C25—H25119.7
N17—C17—C14118.2 (3)C24—C25—H25119.7
C17—N17—N27121.8 (2)C25—C26—C21121.3 (3)
C17—N17—H17121.0C25—C26—H26119.4
N27—N17—H17113.7C21—C26—H26119.4
C16—N11—C12—C130.3 (5)N17—N27—C27—C21178.8 (2)
N11—C12—C13—C140.7 (5)N27—C27—C21—C22177.6 (3)
C12—C13—C14—C150.0 (4)N27—C27—C21—C260.6 (4)
C12—C13—C14—C17175.7 (3)C26—C21—C22—C231.5 (4)
C13—C14—C15—C160.9 (4)C27—C21—C22—C23179.8 (3)
C17—C14—C15—C16176.8 (3)C26—C21—C22—Br22178.5 (2)
C12—N11—C16—C150.7 (5)C27—C21—C22—Br220.2 (4)
C14—C15—C16—N111.3 (5)C21—C22—C23—C241.1 (4)
C15—C14—C17—O137.8 (4)Br22—C22—C23—C24178.9 (2)
C13—C14—C17—O1137.9 (3)C22—C23—C24—C250.5 (4)
C15—C14—C17—N17143.3 (3)C23—C24—C25—C261.7 (4)
C13—C14—C17—N1741.0 (4)C24—C25—C26—C211.2 (4)
O1—C17—N17—N27167.9 (3)C22—C21—C26—C250.3 (4)
C14—C17—N17—N2713.2 (4)C27—C21—C26—C25178.7 (3)
C17—N17—N27—C27171.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.962.002.955 (3)172
C23—H23···O1ii0.952.523.213 (4)130
C16—H16···Cg3iii0.952.873.743 (3)154
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+3/2.
(IX) N-isonicotinoyl 3-bromobenzaldehydehydrazone top
Crystal data top
C13H10BrN3OF(000) = 608
Mr = 304.15Dx = 1.698 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2733 reflections
a = 7.4578 (2) Åθ = 2.9–27.5°
b = 11.3264 (3) ŵ = 3.45 mm1
c = 14.3558 (3) ÅT = 120 K
β = 101.119 (2)°Plate, colourless
V = 1189.87 (5) Å30.40 × 0.20 × 0.02 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2733 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2231 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ & ω scansh = 99
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1414
Tmin = 0.340, Tmax = 0.934l = 1818
14830 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.5661P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
2733 reflectionsΔρmax = 0.41 e Å3
164 parametersΔρmin = 0.55 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (8)
Crystal data top
C13H10BrN3OV = 1189.87 (5) Å3
Mr = 304.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4578 (2) ŵ = 3.45 mm1
b = 11.3264 (3) ÅT = 120 K
c = 14.3558 (3) Å0.40 × 0.20 × 0.02 mm
β = 101.119 (2)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2733 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2231 reflections with I > 2σ(I)
Tmin = 0.340, Tmax = 0.934Rint = 0.043
14830 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.07Δρmax = 0.41 e Å3
2733 reflectionsΔρmin = 0.55 e Å3
164 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.3372 (2)0.02360 (14)0.21574 (11)0.0184 (3)
C120.2566 (3)0.12994 (17)0.20990 (13)0.0182 (4)
C130.2756 (3)0.20922 (16)0.28486 (13)0.0165 (4)
C140.3841 (2)0.17842 (16)0.37143 (13)0.0143 (4)
C150.4734 (3)0.07005 (17)0.37751 (13)0.0169 (4)
C160.4457 (3)0.00363 (17)0.29919 (13)0.0183 (4)
C170.4060 (3)0.25088 (16)0.46118 (13)0.0167 (4)
O10.4929 (2)0.21345 (13)0.53588 (9)0.0267 (3)
N170.3190 (2)0.35760 (14)0.45373 (10)0.0160 (3)
N270.3313 (2)0.42289 (14)0.53563 (11)0.0163 (3)
C270.2438 (3)0.52064 (17)0.52817 (13)0.0164 (4)
C210.2519 (3)0.59632 (15)0.61166 (13)0.0152 (4)
C220.3607 (3)0.56599 (17)0.69924 (13)0.0160 (4)
C230.3653 (3)0.64066 (17)0.77589 (13)0.0175 (4)
Br230.51223 (3)0.597016 (19)0.894103 (14)0.03140 (11)
C240.2666 (3)0.74551 (17)0.76882 (14)0.0212 (4)
C250.1616 (3)0.77495 (18)0.68193 (14)0.0222 (4)
C260.1521 (3)0.70134 (17)0.60387 (14)0.0195 (4)
H120.18230.15220.15110.022*
H130.21540.28350.27710.020*
H150.55230.04700.43470.020*
H160.50680.07760.30460.022*
H170.26790.38980.39930.019*
H270.17370.54410.46860.020*
H220.43020.49520.70590.019*
H240.27130.79550.82240.025*
H250.09470.84680.67540.027*
H260.07730.72250.54490.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0217 (8)0.0178 (8)0.0153 (8)0.0007 (7)0.0023 (7)0.0033 (6)
C120.0218 (10)0.0186 (9)0.0130 (9)0.0001 (8)0.0009 (8)0.0008 (7)
C130.0204 (10)0.0131 (9)0.0161 (9)0.0010 (7)0.0036 (8)0.0005 (7)
C140.0151 (9)0.0142 (9)0.0142 (8)0.0023 (7)0.0045 (7)0.0002 (7)
C150.0177 (9)0.0178 (9)0.0143 (9)0.0005 (7)0.0006 (7)0.0002 (7)
C160.0197 (10)0.0166 (9)0.0181 (9)0.0015 (8)0.0021 (8)0.0010 (7)
C170.0208 (10)0.0148 (9)0.0139 (8)0.0030 (7)0.0023 (7)0.0008 (7)
O10.0411 (9)0.0208 (7)0.0146 (7)0.0068 (7)0.0038 (6)0.0013 (6)
N170.0233 (8)0.0146 (8)0.0089 (7)0.0005 (7)0.0000 (6)0.0015 (6)
N270.0213 (8)0.0159 (8)0.0119 (7)0.0025 (6)0.0035 (6)0.0026 (6)
C270.0202 (9)0.0169 (9)0.0120 (8)0.0018 (8)0.0029 (7)0.0011 (7)
C210.0176 (9)0.0144 (9)0.0145 (9)0.0022 (7)0.0054 (7)0.0001 (7)
C220.0187 (9)0.0142 (9)0.0153 (9)0.0005 (7)0.0039 (7)0.0000 (7)
C230.0222 (10)0.0174 (9)0.0133 (9)0.0033 (8)0.0042 (7)0.0002 (7)
Br230.04584 (17)0.02825 (15)0.01556 (13)0.00163 (10)0.00544 (10)0.00469 (8)
C240.0276 (11)0.0170 (9)0.0214 (9)0.0033 (8)0.0113 (8)0.0059 (8)
C250.0260 (10)0.0149 (9)0.0280 (10)0.0031 (8)0.0109 (9)0.0001 (8)
C260.0226 (10)0.0184 (9)0.0177 (9)0.0006 (8)0.0044 (8)0.0030 (7)
Geometric parameters (Å, º) top
N11—C121.341 (3)N27—C271.279 (3)
N11—C161.346 (2)C27—C211.465 (2)
C12—C131.388 (3)C27—H270.95
C12—H120.95C21—C261.396 (3)
C13—C141.390 (2)C21—C221.401 (3)
C13—H130.95C22—C231.383 (3)
C14—C151.391 (3)C22—H220.95
C14—C171.510 (2)C23—C241.390 (3)
C15—C161.383 (3)C23—Br231.8996 (19)
C15—H150.95C24—C251.380 (3)
C16—H160.95C24—H240.95
C17—O11.217 (2)C25—C261.387 (3)
C17—N171.366 (2)C25—H250.95
N17—N271.377 (2)C26—H260.95
N17—H170.8799
C12—N11—C16116.52 (16)C27—N27—N17116.40 (16)
N11—C12—C13123.72 (17)N27—C27—C21119.87 (17)
N11—C12—H12118.1N27—C27—H27120.1
C13—C12—H12118.1C21—C27—H27120.1
C12—C13—C14119.06 (17)C26—C21—C22119.22 (17)
C12—C13—H13120.5C26—C21—C27119.71 (17)
C14—C13—H13120.5C22—C21—C27121.06 (17)
C13—C14—C15117.80 (17)C23—C22—C21119.03 (18)
C13—C14—C17125.12 (16)C23—C22—H22120.5
C15—C14—C17117.02 (16)C21—C22—H22120.5
C16—C15—C14119.12 (17)C22—C23—C24122.19 (18)
C16—C15—H15120.4C22—C23—Br23118.24 (15)
C14—C15—H15120.4C24—C23—Br23119.57 (14)
N11—C16—C15123.72 (18)C25—C24—C23118.19 (18)
N11—C16—H16118.1C25—C24—H24120.9
C15—C16—H16118.1C23—C24—H24120.9
O1—C17—N17122.77 (17)C24—C25—C26121.12 (18)
O1—C17—C14120.94 (17)C24—C25—H25119.4
N17—C17—C14116.26 (15)C26—C25—H25119.4
C17—N17—N27117.12 (15)C25—C26—C21120.24 (18)
C17—N17—H17123.6C25—C26—H26119.9
N27—N17—H17118.8C21—C26—H26119.9
C16—N11—C12—C131.9 (3)C17—N17—N27—C27177.62 (17)
N11—C12—C13—C140.1 (3)N17—N27—C27—C21179.09 (16)
C12—C13—C14—C152.0 (3)N27—C27—C21—C26178.18 (18)
C12—C13—C14—C17174.98 (18)N27—C27—C21—C222.8 (3)
C13—C14—C15—C162.3 (3)C26—C21—C22—C230.4 (3)
C17—C14—C15—C16174.90 (17)C27—C21—C22—C23179.44 (17)
C12—N11—C16—C151.5 (3)C21—C22—C23—C240.5 (3)
C14—C15—C16—N110.6 (3)C21—C22—C23—Br23179.51 (14)
C13—C14—C17—O1174.48 (19)C22—C23—C24—C250.2 (3)
C15—C14—C17—O12.5 (3)Br23—C23—C24—C25179.79 (15)
C13—C14—C17—N173.6 (3)C23—C24—C25—C261.0 (3)
C15—C14—C17—N17179.34 (17)C24—C25—C26—C211.1 (3)
O1—C17—N17—N270.6 (3)C22—C21—C26—C250.4 (3)
C14—C17—N17—N27177.46 (15)C27—C21—C26—C25178.65 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.882.273.117 (2)163
C12—H12···O1ii0.952.483.371 (2)156
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2.
(X) N-isonicotinoyl 4-bromobenzaldehydehydrazone top
Crystal data top
C13H10BrN3O·H2OF(000) = 1296
Mr = 322.17Dx = 1.658 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5916 reflections
a = 14.2570 (3) Åθ = 1.6–27.5°
b = 14.6299 (4) ŵ = 3.19 mm1
c = 14.1669 (4) ÅT = 120 K
β = 119.152 (2)°Block, colourless
V = 2580.61 (12) Å30.38 × 0.24 × 0.24 mm
Z = 8
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5916 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode5220 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.6°
ϕ & ω scansh = 1817
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1818
Tmin = 0.341, Tmax = 0.465l = 1618
28990 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.017P)2 + 24.843P]
where P = (Fo2 + 2Fc2)/3
5916 reflections(Δ/σ)max < 0.001
344 parametersΔρmax = 2.26 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
C13H10BrN3O·H2OV = 2580.61 (12) Å3
Mr = 322.17Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.2570 (3) ŵ = 3.19 mm1
b = 14.6299 (4) ÅT = 120 K
c = 14.1669 (4) Å0.38 × 0.24 × 0.24 mm
β = 119.152 (2)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5916 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
5220 reflections with I > 2σ(I)
Tmin = 0.341, Tmax = 0.465Rint = 0.045
28990 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.017P)2 + 24.843P]
where P = (Fo2 + 2Fc2)/3
5916 reflectionsΔρmax = 2.26 e Å3
344 parametersΔρmin = 0.73 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.5800 (4)0.0327 (4)0.7369 (4)0.0217 (11)
C120.5383 (5)0.1105 (4)0.6845 (5)0.0217 (13)
C130.5930 (5)0.1913 (4)0.6997 (5)0.0205 (12)
C140.7025 (4)0.1925 (4)0.7756 (5)0.0153 (11)
C150.7502 (4)0.1119 (4)0.8281 (5)0.0174 (11)
C160.6865 (5)0.0347 (4)0.8089 (5)0.0231 (13)
C170.7729 (5)0.2753 (4)0.8043 (5)0.0171 (12)
O10.8715 (3)0.2673 (3)0.8431 (4)0.0218 (9)
N170.7221 (4)0.3567 (3)0.7862 (4)0.0193 (11)
N270.7829 (4)0.4360 (3)0.8169 (4)0.0197 (11)
C270.7274 (5)0.5099 (4)0.7989 (5)0.0218 (13)
C210.7799 (5)0.6002 (4)0.8265 (5)0.0188 (12)
C220.7158 (5)0.6780 (4)0.8020 (5)0.0208 (13)
C230.7600 (5)0.7643 (4)0.8269 (5)0.0211 (13)
C240.8712 (5)0.7725 (4)0.8780 (5)0.0196 (12)
Br240.93391 (5)0.89108 (4)0.91670 (6)0.02576 (17)
C250.9369 (5)0.6969 (4)0.9046 (5)0.0201 (12)
C260.8930 (5)0.6114 (4)0.8797 (6)0.0233 (13)
O20.5001 (4)0.4045 (3)0.6585 (4)0.0286 (11)
N310.1127 (5)0.0114 (4)0.3484 (5)0.0245 (12)
C320.0596 (5)0.0851 (4)0.3548 (5)0.0218 (13)
C330.1056 (5)0.1708 (4)0.3845 (5)0.0190 (12)
C340.2117 (5)0.1819 (4)0.4092 (5)0.0165 (11)
C350.2665 (5)0.1062 (5)0.4041 (6)0.0240 (13)
C360.2147 (6)0.0241 (5)0.3723 (5)0.0245 (14)
C370.2712 (5)0.2711 (4)0.4455 (5)0.0193 (12)
O30.3693 (3)0.2717 (3)0.5027 (4)0.0266 (10)
N370.2100 (4)0.3471 (4)0.4120 (4)0.0198 (11)
N470.2627 (4)0.4296 (4)0.4440 (4)0.0207 (11)
C470.2064 (5)0.5023 (4)0.4067 (5)0.0208 (13)
C410.2604 (5)0.5919 (4)0.4393 (5)0.0213 (13)
C420.1989 (5)0.6725 (4)0.4157 (5)0.0215 (13)
C430.2491 (5)0.7565 (5)0.4539 (5)0.0217 (13)
C440.3603 (5)0.7598 (4)0.5122 (5)0.0209 (12)
Br440.43156 (5)0.87230 (4)0.56999 (6)0.02707 (17)
C450.4226 (5)0.6818 (5)0.5320 (5)0.0224 (13)
C460.3720 (5)0.5987 (4)0.4955 (5)0.0233 (13)
O40.0157 (4)0.3575 (4)0.2779 (4)0.0356 (13)
H120.46430.11020.63200.026*
H130.55770.24460.66000.025*
H150.82530.10940.87660.021*
H160.71940.01940.84820.028*
H170.65170.35930.75550.023*
H270.65150.50610.76730.026*
H220.64000.67140.76750.025*
H230.71550.81690.80950.025*
H251.01270.70420.94010.024*
H260.93830.55930.89820.028*
H2A0.43850.38980.58560.043*
H2B0.46700.43210.69990.043*
H320.01310.07780.33810.026*
H330.06530.22120.38790.023*
H350.33990.11100.42270.029*
H360.25330.02660.36670.029*
H370.13980.34400.37160.024*
H470.13130.49870.35890.025*
H420.12290.66950.37360.026*
H430.20790.81080.44020.026*
H450.49880.68560.56990.027*
H460.41410.54500.50900.028*
H4A0.02910.41800.24080.053*
H4B0.07850.34720.28980.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.021 (3)0.017 (2)0.025 (3)0.004 (2)0.010 (2)0.003 (2)
C120.016 (3)0.021 (3)0.021 (3)0.001 (2)0.004 (2)0.000 (2)
C130.020 (3)0.019 (3)0.019 (3)0.001 (2)0.007 (2)0.002 (2)
C140.013 (3)0.017 (3)0.016 (3)0.001 (2)0.007 (2)0.003 (2)
C150.011 (2)0.020 (3)0.019 (3)0.000 (2)0.005 (2)0.000 (2)
C160.025 (3)0.016 (3)0.026 (3)0.001 (2)0.009 (3)0.001 (2)
C170.016 (3)0.017 (3)0.018 (3)0.001 (2)0.008 (2)0.000 (2)
O10.0115 (19)0.020 (2)0.031 (2)0.0019 (16)0.0080 (18)0.0015 (19)
N170.013 (2)0.014 (2)0.030 (3)0.0019 (19)0.009 (2)0.001 (2)
N270.021 (3)0.014 (2)0.022 (3)0.003 (2)0.009 (2)0.002 (2)
C270.020 (3)0.017 (3)0.024 (3)0.003 (2)0.007 (3)0.006 (2)
C210.022 (3)0.014 (3)0.020 (3)0.002 (2)0.009 (2)0.005 (2)
C220.015 (3)0.019 (3)0.026 (3)0.002 (2)0.008 (2)0.003 (2)
C230.020 (3)0.016 (3)0.024 (3)0.001 (2)0.009 (3)0.002 (2)
C240.020 (3)0.016 (3)0.023 (3)0.003 (2)0.010 (2)0.001 (2)
Br240.0199 (3)0.0163 (3)0.0362 (4)0.0027 (2)0.0099 (3)0.0001 (3)
C250.017 (3)0.023 (3)0.020 (3)0.001 (2)0.009 (2)0.000 (2)
C260.028 (3)0.014 (3)0.035 (4)0.006 (2)0.021 (3)0.000 (3)
O20.017 (2)0.030 (3)0.030 (2)0.0081 (19)0.0045 (19)0.007 (2)
N310.028 (3)0.020 (3)0.025 (3)0.003 (2)0.013 (2)0.003 (2)
C320.018 (3)0.021 (3)0.025 (3)0.001 (2)0.010 (2)0.002 (2)
C330.017 (3)0.020 (3)0.018 (3)0.002 (2)0.007 (2)0.003 (2)
C340.015 (3)0.017 (3)0.014 (3)0.002 (2)0.004 (2)0.000 (2)
C350.017 (3)0.027 (3)0.032 (3)0.000 (3)0.015 (3)0.003 (3)
C360.028 (3)0.020 (3)0.025 (3)0.006 (3)0.013 (3)0.001 (3)
C370.016 (3)0.023 (3)0.019 (3)0.003 (2)0.009 (2)0.004 (2)
O30.014 (2)0.025 (2)0.033 (3)0.0021 (18)0.0046 (19)0.003 (2)
N370.014 (2)0.016 (2)0.025 (3)0.0051 (19)0.006 (2)0.006 (2)
N470.020 (2)0.019 (3)0.023 (3)0.007 (2)0.011 (2)0.004 (2)
C470.018 (3)0.018 (3)0.025 (3)0.002 (2)0.010 (2)0.001 (2)
C410.022 (3)0.019 (3)0.023 (3)0.003 (2)0.011 (3)0.002 (2)
C420.018 (3)0.019 (3)0.024 (3)0.003 (2)0.007 (2)0.002 (2)
C430.020 (3)0.019 (3)0.024 (3)0.002 (2)0.010 (3)0.003 (2)
C440.021 (3)0.020 (3)0.022 (3)0.004 (2)0.011 (2)0.001 (2)
Br440.0260 (3)0.0209 (3)0.0341 (4)0.0077 (3)0.0145 (3)0.0065 (3)
C450.014 (3)0.027 (3)0.023 (3)0.002 (2)0.007 (2)0.000 (3)
C460.030 (3)0.015 (3)0.027 (3)0.003 (3)0.015 (3)0.003 (2)
O40.018 (2)0.037 (3)0.045 (3)0.005 (2)0.009 (2)0.019 (2)
Geometric parameters (Å, º) top
N11—C121.332 (8)N31—C361.336 (9)
N11—C161.356 (8)N31—C321.345 (8)
C12—C131.374 (9)C32—C331.383 (9)
C12—H120.95C32—H320.95
C13—C141.399 (8)C33—C341.386 (8)
C13—H130.95C33—H330.95
C14—C151.383 (8)C34—C351.376 (9)
C14—C171.497 (8)C34—C371.504 (8)
C15—C161.391 (9)C35—C361.366 (9)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.240 (7)C37—O31.228 (7)
C17—N171.352 (8)C37—N371.349 (8)
N17—N271.385 (7)N37—N471.377 (7)
N17—H170.88N37—H370.88
N27—C271.290 (8)N47—C471.282 (8)
C27—C211.474 (8)C47—C411.475 (9)
C27—H270.95C47—H470.95
C21—C221.392 (9)C41—C461.394 (9)
C21—C261.418 (9)C41—C421.409 (9)
C22—C231.378 (9)C42—C431.393 (9)
C22—H220.95C42—H420.95
C23—C241.391 (9)C43—C441.386 (9)
C23—H230.95C43—H430.95
C24—C251.379 (8)C44—C451.388 (9)
C24—Br241.905 (6)C44—Br441.898 (6)
C25—C261.366 (9)C45—C461.379 (9)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
O2—H2A1.00O4—H4A1.00
O2—H2B1.00O4—H4B1.00
C12—N11—C16115.7 (5)C36—N31—C32116.7 (6)
N11—C12—C13125.7 (6)N31—C32—C33123.3 (6)
N11—C12—H12117.2N31—C32—H32118.4
C13—C12—H12117.2C33—C32—H32118.4
C12—C13—C14117.9 (6)C32—C33—C34118.7 (6)
C12—C13—H13121.1C32—C33—H33120.7
C14—C13—H13121.1C34—C33—H33120.7
C15—C14—C13118.3 (5)C35—C34—C33118.1 (6)
C15—C14—C17117.0 (5)C35—C34—C37118.4 (5)
C13—C14—C17124.6 (5)C33—C34—C37123.5 (6)
C14—C15—C16119.0 (5)C36—C35—C34119.7 (6)
C14—C15—H15120.5C36—C35—H35120.1
C16—C15—H15120.5C34—C35—H35120.1
N11—C16—C15123.4 (6)N31—C36—C35123.5 (6)
N11—C16—H16118.3N31—C36—H36118.2
C15—C16—H16118.3C35—C36—H36118.2
O1—C17—N17123.6 (6)O3—C37—N37124.0 (6)
O1—C17—C14120.6 (5)O3—C37—C34120.2 (6)
N17—C17—C14115.8 (5)N37—C37—C34115.7 (5)
C17—N17—N27118.9 (5)C37—N37—N47116.8 (5)
C17—N17—H17120.6C37—N37—H37121.6
N27—N17—H17120.6N47—N37—H37121.6
C27—N27—N17114.2 (5)C47—N47—N37117.4 (5)
N27—C27—C21121.0 (6)N47—C47—C41118.8 (6)
N27—C27—H27119.5N47—C47—H47120.6
C21—C27—H27119.5C41—C47—H47120.6
C22—C21—C26118.4 (6)C46—C41—C42118.7 (6)
C22—C21—C27118.7 (6)C46—C41—C47121.3 (6)
C26—C21—C27122.9 (6)C42—C41—C47120.0 (6)
C23—C22—C21121.5 (6)C43—C42—C41120.3 (6)
C23—C22—H22119.2C43—C42—H42119.9
C21—C22—H22119.2C41—C42—H42119.9
C22—C23—C24118.4 (6)C44—C43—C42118.9 (6)
C22—C23—H23120.8C44—C43—H43120.5
C24—C23—H23120.8C42—C43—H43120.5
C25—C24—C23121.6 (6)C43—C44—C45121.7 (6)
C25—C24—Br24119.4 (5)C43—C44—Br44120.2 (5)
C23—C24—Br24119.0 (5)C45—C44—Br44118.0 (5)
C26—C25—C24120.0 (6)C46—C45—C44118.8 (6)
C26—C25—H25120.0C46—C45—H45120.6
C24—C25—H25120.0C44—C45—H45120.6
C25—C26—C21120.1 (6)C45—C46—C41121.4 (6)
C25—C26—H26119.9C45—C46—H46119.3
C21—C26—H26119.9C41—C46—H46119.3
H2A—O2—H2B105.4H4A—O4—H4B105.3
C16—N11—C12—C131.9 (10)C36—N31—C32—C330.2 (10)
N11—C12—C13—C141.0 (10)N31—C32—C33—C340.1 (10)
C12—C13—C14—C152.2 (9)C32—C33—C34—C350.8 (9)
C12—C13—C14—C17178.1 (6)C32—C33—C34—C37178.2 (6)
C13—C14—C15—C164.2 (9)C33—C34—C35—C362.0 (10)
C17—C14—C15—C16176.1 (6)C37—C34—C35—C36179.5 (6)
C12—N11—C16—C150.2 (10)C32—N31—C36—C351.4 (10)
C14—C15—C16—N113.3 (10)C34—C35—C36—N312.3 (11)
C15—C14—C17—O123.3 (9)C35—C34—C37—O324.5 (9)
C13—C14—C17—O1156.4 (6)C33—C34—C37—O3152.9 (6)
C15—C14—C17—N17156.0 (6)C35—C34—C37—N37156.1 (6)
C13—C14—C17—N1724.2 (9)C33—C34—C37—N3726.6 (9)
O1—C17—N17—N273.1 (9)O3—C37—N37—N470.7 (9)
C14—C17—N17—N27176.2 (5)C34—C37—N37—N47179.9 (5)
C17—N17—N27—C27178.3 (6)C37—N37—N47—C47175.3 (6)
N17—N27—C27—C21179.8 (6)N37—N47—C47—C41179.9 (6)
N27—C27—C21—C22177.9 (6)N47—C47—C41—C4610.0 (10)
N27—C27—C21—C263.9 (10)N47—C47—C41—C42168.7 (6)
C26—C21—C22—C231.0 (10)C46—C41—C42—C433.9 (10)
C27—C21—C22—C23179.3 (6)C47—C41—C42—C43174.7 (6)
C21—C22—C23—C240.3 (10)C41—C42—C43—C442.1 (10)
C22—C23—C24—C250.5 (10)C42—C43—C44—C451.0 (10)
C22—C23—C24—Br24178.2 (5)C42—C43—C44—Br44177.8 (5)
C23—C24—C25—C260.6 (10)C43—C44—C45—C462.3 (10)
Br24—C24—C25—C26178.3 (5)Br44—C44—C45—C46176.6 (5)
C24—C25—C26—C210.1 (10)C44—C45—C46—C410.3 (10)
C22—C21—C26—C250.9 (10)C42—C41—C46—C452.7 (10)
C27—C21—C26—C25179.1 (6)C47—C41—C46—C45175.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O20.882.032.864 (7)159
N37—H37···O40.881.962.834 (7)171
O2—H2A···O31.002.052.848 (7)135
O2—H2A···N471.002.403.287 (7)148
O2—H2B···N11i1.002.002.944 (7)156
O4—H4A···N31ii1.001.852.789 (7)155
O4—H4B···O1iii1.002.102.867 (7)132
C13—H13···O20.952.483.327 (8)149
C27—H27···O20.952.453.249 (8)142
C33—H33···O40.952.453.191 (8)135
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1/2, z+1/2; (iii) x1, y+1/2, z1/2.
(XI) N-isonicotinoyl 2-methoxybenzaldehydehydrazone top
Crystal data top
C14H13N3O2F(000) = 1072
Mr = 255.27Dx = 1.282 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6048 reflections
a = 9.8899 (3) Åθ = 1.8–27.5°
b = 15.8189 (4) ŵ = 0.09 mm1
c = 17.0380 (5) ÅT = 120 K
β = 97.236 (2)°Needle, colourless
V = 2644.32 (13) Å30.40 × 0.08 × 0.05 mm
Z = 8
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6048 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4196 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.8°
ϕ & ω scansh = 1212
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 2020
Tmin = 0.974, Tmax = 0.996l = 2222
33120 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0411P)2 + 0.7605P]
where P = (Fo2 + 2Fc2)/3
6048 reflections(Δ/σ)max < 0.001
345 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C14H13N3O2V = 2644.32 (13) Å3
Mr = 255.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.8899 (3) ŵ = 0.09 mm1
b = 15.8189 (4) ÅT = 120 K
c = 17.0380 (5) Å0.40 × 0.08 × 0.05 mm
β = 97.236 (2)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6048 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
4196 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.996Rint = 0.053
33120 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
6048 reflectionsΔρmin = 0.22 e Å3
345 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.24285 (13)0.46023 (9)0.50833 (8)0.0322 (3)
C120.32844 (16)0.41087 (10)0.47406 (9)0.0283 (4)
C130.40675 (15)0.43834 (9)0.41718 (9)0.0235 (3)
C140.39903 (15)0.52289 (9)0.39537 (9)0.0218 (3)
C150.31165 (16)0.57525 (10)0.43039 (9)0.0276 (4)
C160.23589 (16)0.54106 (11)0.48509 (10)0.0325 (4)
C170.48363 (15)0.56099 (9)0.33778 (9)0.0221 (3)
O10.53411 (11)0.63194 (6)0.34959 (6)0.0274 (3)
N170.49667 (13)0.51292 (8)0.27459 (7)0.0251 (3)
N270.57270 (13)0.54065 (8)0.21639 (8)0.0261 (3)
C270.57442 (15)0.48788 (10)0.15936 (9)0.0267 (4)
C210.64948 (15)0.50540 (10)0.09265 (9)0.0264 (4)
C220.65393 (16)0.44324 (10)0.03400 (9)0.0286 (4)
O220.58912 (12)0.36911 (7)0.04609 (7)0.0355 (3)
C2210.58917 (19)0.30389 (12)0.01257 (11)0.0441 (5)
C230.72338 (18)0.45857 (12)0.03076 (10)0.0369 (4)
C240.78696 (19)0.53524 (12)0.03723 (11)0.0437 (5)
C250.78403 (19)0.59739 (12)0.01980 (11)0.0424 (5)
C260.71520 (17)0.58195 (11)0.08420 (10)0.0334 (4)
N310.07965 (14)0.22436 (9)0.07857 (9)0.0349 (3)
C320.03832 (17)0.18196 (11)0.08414 (11)0.0358 (4)
C330.15787 (16)0.20838 (10)0.12824 (10)0.0293 (4)
C340.15779 (15)0.28436 (9)0.16890 (9)0.0225 (3)
C350.03634 (15)0.32914 (10)0.16381 (9)0.0265 (4)
C360.07832 (16)0.29678 (10)0.11920 (10)0.0310 (4)
C370.28144 (15)0.32300 (9)0.21527 (9)0.0225 (3)
O30.28046 (10)0.39774 (6)0.23568 (6)0.0286 (3)
N370.39079 (12)0.27253 (8)0.23228 (8)0.0260 (3)
N470.51289 (12)0.30839 (8)0.26555 (7)0.0253 (3)
C470.61228 (16)0.25583 (10)0.27639 (9)0.0274 (4)
C410.75064 (15)0.28293 (10)0.30607 (9)0.0262 (4)
C420.85552 (16)0.22238 (10)0.31390 (9)0.0290 (4)
O420.81679 (11)0.14148 (7)0.29343 (7)0.0373 (3)
C4210.92104 (19)0.08051 (11)0.28666 (13)0.0474 (5)
C430.98840 (17)0.24604 (12)0.34073 (10)0.0358 (4)
C441.01772 (17)0.32986 (12)0.35887 (10)0.0387 (4)
C450.91641 (17)0.39039 (12)0.35039 (10)0.0370 (4)
C460.78383 (17)0.36693 (11)0.32432 (9)0.0311 (4)
H120.33590.35330.48980.034*
H130.46420.40030.39370.028*
H150.30410.63350.41700.033*
H160.17470.57730.50780.039*
H170.45660.46320.26980.030*
H270.52570.43620.16050.032*
H22A0.54660.32530.06380.066*
H22B0.53780.25500.00300.066*
H22C0.68320.28690.01690.066*
H230.72690.41640.07020.044*
H240.83370.54570.08170.052*
H250.82870.64990.01480.051*
H260.71280.62450.12340.040*
H320.04000.13030.05590.043*
H330.23830.17520.13060.035*
H350.03210.38150.19070.032*
H360.16100.32780.11730.037*
H370.38500.21790.22250.031*
H470.59550.19770.26480.033*
H42A0.98160.10110.24950.071*
H42B0.87940.02710.26720.071*
H42C0.97380.07140.33860.071*
H431.05890.20490.34660.043*
H441.10870.34590.37740.046*
H450.93780.44790.36240.044*
H460.71420.40860.31870.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0254 (7)0.0439 (9)0.0269 (8)0.0010 (6)0.0025 (6)0.0029 (6)
C120.0279 (9)0.0289 (9)0.0267 (9)0.0040 (7)0.0023 (7)0.0029 (7)
C130.0234 (8)0.0228 (8)0.0232 (8)0.0008 (6)0.0007 (6)0.0030 (6)
C140.0180 (7)0.0252 (8)0.0206 (8)0.0016 (6)0.0041 (6)0.0024 (6)
C150.0274 (9)0.0269 (8)0.0273 (9)0.0044 (7)0.0017 (7)0.0003 (7)
C160.0259 (9)0.0426 (10)0.0284 (9)0.0081 (7)0.0013 (7)0.0028 (8)
C170.0201 (8)0.0202 (8)0.0246 (8)0.0008 (6)0.0025 (6)0.0014 (6)
O10.0295 (6)0.0216 (6)0.0298 (6)0.0050 (5)0.0017 (5)0.0008 (5)
N170.0285 (7)0.0214 (7)0.0262 (7)0.0067 (5)0.0072 (6)0.0009 (6)
N270.0237 (7)0.0293 (7)0.0257 (7)0.0037 (5)0.0041 (6)0.0039 (6)
C270.0243 (8)0.0279 (8)0.0275 (9)0.0027 (7)0.0016 (7)0.0027 (7)
C210.0222 (8)0.0324 (9)0.0239 (8)0.0003 (6)0.0004 (7)0.0045 (7)
C220.0234 (8)0.0339 (9)0.0276 (9)0.0024 (7)0.0006 (7)0.0054 (7)
O220.0371 (7)0.0339 (7)0.0363 (7)0.0028 (5)0.0073 (6)0.0061 (5)
C2210.0439 (11)0.0432 (11)0.0445 (11)0.0015 (9)0.0024 (9)0.0132 (9)
C230.0381 (10)0.0460 (11)0.0271 (9)0.0054 (8)0.0055 (8)0.0000 (8)
C240.0454 (11)0.0567 (12)0.0311 (10)0.0025 (9)0.0135 (9)0.0091 (9)
C250.0436 (11)0.0473 (11)0.0373 (11)0.0106 (9)0.0090 (9)0.0085 (9)
C260.0341 (10)0.0377 (10)0.0283 (9)0.0046 (8)0.0031 (8)0.0026 (7)
N310.0255 (8)0.0322 (8)0.0453 (9)0.0034 (6)0.0017 (6)0.0044 (7)
C320.0287 (9)0.0307 (9)0.0469 (11)0.0030 (7)0.0001 (8)0.0111 (8)
C330.0221 (8)0.0287 (9)0.0370 (10)0.0008 (7)0.0030 (7)0.0059 (7)
C340.0211 (8)0.0242 (8)0.0223 (8)0.0024 (6)0.0032 (6)0.0010 (6)
C350.0253 (8)0.0243 (8)0.0299 (9)0.0006 (6)0.0033 (7)0.0003 (7)
C360.0221 (8)0.0303 (9)0.0398 (10)0.0025 (7)0.0007 (7)0.0030 (8)
C370.0221 (8)0.0243 (8)0.0217 (8)0.0013 (6)0.0051 (6)0.0017 (6)
O30.0249 (6)0.0237 (6)0.0366 (7)0.0001 (4)0.0018 (5)0.0076 (5)
N370.0221 (7)0.0220 (7)0.0328 (8)0.0020 (5)0.0010 (6)0.0066 (6)
N470.0198 (7)0.0291 (7)0.0267 (7)0.0030 (6)0.0020 (6)0.0055 (6)
C470.0264 (9)0.0270 (8)0.0282 (9)0.0012 (7)0.0011 (7)0.0042 (7)
C410.0233 (8)0.0339 (9)0.0211 (8)0.0022 (7)0.0012 (7)0.0023 (7)
C420.0269 (9)0.0349 (9)0.0249 (9)0.0024 (7)0.0019 (7)0.0033 (7)
O420.0255 (6)0.0319 (7)0.0538 (8)0.0028 (5)0.0021 (6)0.0039 (6)
C4210.0348 (11)0.0341 (10)0.0735 (15)0.0086 (8)0.0076 (10)0.0063 (10)
C430.0244 (9)0.0505 (11)0.0323 (10)0.0018 (8)0.0030 (7)0.0058 (8)
C440.0251 (9)0.0578 (12)0.0326 (10)0.0106 (8)0.0010 (8)0.0050 (9)
C450.0332 (10)0.0451 (11)0.0332 (10)0.0126 (8)0.0063 (8)0.0104 (8)
C460.0290 (9)0.0368 (10)0.0276 (9)0.0032 (7)0.0038 (7)0.0081 (7)
Geometric parameters (Å, º) top
N11—C161.338 (2)N31—C361.338 (2)
N11—C121.339 (2)N31—C321.339 (2)
C12—C131.385 (2)C32—C331.383 (2)
C12—H120.95C32—H320.95
C13—C141.388 (2)C33—C341.387 (2)
C13—H130.95C33—H330.95
C14—C151.385 (2)C34—C351.388 (2)
C14—C171.494 (2)C34—C371.500 (2)
C15—C161.378 (2)C35—C361.382 (2)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.2346 (17)C37—O31.2327 (17)
C17—N171.3374 (19)C37—N371.3461 (19)
N17—N271.3889 (16)N37—N471.3889 (17)
N17—H170.88N37—H370.88
N27—C271.2827 (19)N47—C471.2829 (19)
C27—C211.460 (2)C47—C411.462 (2)
C27—H270.95C47—H470.95
C21—C261.390 (2)C41—C461.394 (2)
C21—C221.407 (2)C41—C421.406 (2)
C22—O221.3645 (19)C42—O421.3685 (19)
C22—C231.392 (2)C42—C431.387 (2)
O22—C2211.437 (2)O42—C4211.427 (2)
C221—H22A0.98C421—H42A0.98
C221—H22B0.98C421—H42B0.98
C221—H22C0.98C421—H42C0.98
C23—C241.377 (3)C43—C441.384 (3)
C23—H230.95C43—H430.95
C24—C251.385 (3)C44—C451.380 (2)
C24—H240.95C44—H440.95
C25—C261.384 (2)C45—C461.381 (2)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
C16—N11—C12116.11 (14)C36—N31—C32116.15 (14)
N11—C12—C13124.24 (15)N31—C32—C33124.39 (15)
N11—C12—H12117.9N31—C32—H32117.8
C13—C12—H12117.9C33—C32—H32117.8
C12—C13—C14118.23 (14)C32—C33—C34118.61 (15)
C12—C13—H13120.9C32—C33—H33120.7
C14—C13—H13120.9C34—C33—H33120.7
C15—C14—C13118.51 (14)C33—C34—C35117.77 (14)
C15—C14—C17118.23 (13)C33—C34—C37124.36 (13)
C13—C14—C17123.24 (13)C35—C34—C37117.83 (13)
C16—C15—C14118.59 (15)C36—C35—C34119.30 (14)
C16—C15—H15120.7C36—C35—H35120.4
C14—C15—H15120.7C34—C35—H35120.4
N11—C16—C15124.29 (15)N31—C36—C35123.77 (15)
N11—C16—H16117.9N31—C36—H36118.1
C15—C16—H16117.9C35—C36—H36118.1
O1—C17—N17124.75 (14)O3—C37—N37122.87 (14)
O1—C17—C14120.53 (13)O3—C37—C34120.30 (14)
N17—C17—C14114.71 (13)N37—C37—C34116.83 (13)
C17—N17—N27120.73 (12)C37—N37—N47118.64 (12)
C17—N17—H17119.6C37—N37—H37120.7
N27—N17—H17119.6N47—N37—H37120.7
C27—N27—N17113.30 (12)C47—N47—N37113.89 (12)
N27—C27—C21121.52 (14)N47—C47—C41121.77 (14)
N27—C27—H27119.2N47—C47—H47119.1
C21—C27—H27119.2C41—C47—H47119.1
C26—C21—C22118.58 (14)C46—C41—C42118.55 (15)
C26—C21—C27122.41 (15)C46—C41—C47122.70 (15)
C22—C21—C27119.00 (14)C42—C41—C47118.71 (14)
O22—C22—C23123.87 (15)O42—C42—C43124.01 (15)
O22—C22—C21115.86 (13)O42—C42—C41115.69 (14)
C23—C22—C21120.26 (15)C43—C42—C41120.30 (15)
C22—O22—C221118.09 (13)C42—O42—C421118.09 (13)
O22—C221—H22A109.5O42—C421—H42A109.5
O22—C221—H22B109.5O42—C421—H42B109.5
H22A—C221—H22B109.5H42A—C421—H42B109.5
O22—C221—H22C109.5O42—C421—H42C109.5
H22A—C221—H22C109.5H42A—C421—H42C109.5
H22B—C221—H22C109.5H42B—C421—H42C109.5
C24—C23—C22119.52 (16)C44—C43—C42119.68 (16)
C24—C23—H23120.2C44—C43—H43120.2
C22—C23—H23120.2C42—C43—H43120.2
C23—C24—C25121.25 (16)C45—C44—C43120.82 (16)
C23—C24—H24119.4C45—C44—H44119.6
C25—C24—H24119.4C43—C44—H44119.6
C26—C25—C24119.14 (17)C44—C45—C46119.63 (17)
C26—C25—H25120.4C44—C45—H45120.2
C24—C25—H25120.4C46—C45—H45120.2
C25—C26—C21121.25 (16)C45—C46—C41121.01 (16)
C25—C26—H26119.4C45—C46—H46119.5
C21—C26—H26119.4C41—C46—H46119.5
C16—N11—C12—C130.5 (2)C36—N31—C32—C330.1 (3)
N11—C12—C13—C141.6 (2)N31—C32—C33—C340.9 (3)
C12—C13—C14—C151.2 (2)C32—C33—C34—C350.9 (2)
C12—C13—C14—C17176.82 (14)C32—C33—C34—C37176.50 (15)
C13—C14—C15—C160.2 (2)C33—C34—C35—C360.1 (2)
C17—C14—C15—C16178.35 (14)C37—C34—C35—C36177.68 (14)
C12—N11—C16—C151.1 (2)C32—N31—C36—C351.2 (2)
C14—C15—C16—N111.5 (3)C34—C35—C36—N311.2 (2)
C15—C14—C17—O138.7 (2)C33—C34—C37—O3164.71 (14)
C13—C14—C17—O1139.36 (15)C35—C34—C37—O312.7 (2)
C15—C14—C17—N17140.50 (14)C33—C34—C37—N3714.9 (2)
C13—C14—C17—N1741.5 (2)C35—C34—C37—N37167.71 (13)
O1—C17—N17—N270.9 (2)O3—C37—N37—N478.2 (2)
C14—C17—N17—N27179.96 (12)C34—C37—N37—N47171.40 (12)
C17—N17—N27—C27179.37 (14)C37—N37—N47—C47177.15 (13)
N17—N27—C27—C21179.69 (13)N37—N47—C47—C41176.01 (13)
N27—C27—C21—C264.5 (2)N47—C47—C41—C460.1 (2)
N27—C27—C21—C22176.53 (15)N47—C47—C41—C42177.80 (14)
C26—C21—C22—O22179.18 (14)C46—C41—C42—O42178.61 (14)
C27—C21—C22—O221.8 (2)C47—C41—C42—O420.8 (2)
C26—C21—C22—C230.2 (2)C46—C41—C42—C431.2 (2)
C27—C21—C22—C23179.24 (15)C47—C41—C42—C43179.02 (14)
C23—C22—O22—C2211.9 (2)C43—C42—O42—C42110.8 (2)
C21—C22—O22—C221179.24 (14)C41—C42—O42—C421169.09 (15)
O22—C22—C23—C24179.26 (16)O42—C42—C43—C44179.04 (15)
C21—C22—C23—C240.4 (3)C41—C42—C43—C440.8 (2)
C22—C23—C24—C250.5 (3)C42—C43—C44—C450.2 (3)
C23—C24—C25—C260.3 (3)C43—C44—C45—C460.7 (3)
C24—C25—C26—C210.1 (3)C44—C45—C46—C410.3 (3)
C22—C21—C26—C250.1 (2)C42—C41—C46—C450.7 (2)
C27—C21—C26—C25179.07 (16)C47—C41—C46—C45178.40 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O30.882.052.8240 (16)146
N17—H17···N470.882.513.2440 (18)141
N37—H37···O1i0.882.062.7757 (16)138
C33—H33···O1i0.952.343.2550 (19)163
C47—H47···O1i0.952.433.1244 (19)130
Symmetry code: (i) x+1, y1/2, z+1/2.
(XII) N-isonicotinoyl 3-methoxybenzaldehydehydrazone top
Crystal data top
C14H13N3O2F(000) = 536
Mr = 255.27Dx = 1.371 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2827 reflections
a = 8.2938 (4) Åθ = 2.4–27.5°
b = 11.0771 (6) ŵ = 0.10 mm1
c = 13.846 (5) ÅT = 120 K
β = 103.478 (3)°Plate, colourless
V = 1237.0 (5) Å30.15 × 0.15 × 0.04 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2827 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1776 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.4°
ϕ & ω scansh = 1010
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1414
Tmin = 0.977, Tmax = 0.996l = 1717
14906 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0889P)2]
where P = (Fo2 + 2Fc2)/3
2827 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C14H13N3O2V = 1237.0 (5) Å3
Mr = 255.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.2938 (4) ŵ = 0.10 mm1
b = 11.0771 (6) ÅT = 120 K
c = 13.846 (5) Å0.15 × 0.15 × 0.04 mm
β = 103.478 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2827 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1776 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.996Rint = 0.058
14906 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.09Δρmax = 0.28 e Å3
2827 reflectionsΔρmin = 0.33 e Å3
173 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.3443 (2)0.01173 (16)0.21674 (11)0.0221 (4)
C120.2510 (2)0.11174 (19)0.21241 (14)0.0229 (5)
C130.2721 (2)0.19592 (18)0.28839 (13)0.0209 (5)
C140.3938 (2)0.17631 (17)0.37461 (13)0.0185 (4)
C150.4922 (2)0.07418 (19)0.37889 (14)0.0217 (5)
C160.4640 (2)0.00431 (19)0.29901 (14)0.0224 (5)
C170.4226 (2)0.25532 (19)0.46606 (13)0.0198 (5)
O10.51981 (18)0.22403 (13)0.54261 (10)0.0292 (4)
N170.3325 (2)0.35815 (15)0.45832 (11)0.0202 (4)
N270.3498 (2)0.43143 (15)0.54134 (11)0.0200 (4)
C270.2485 (2)0.51952 (18)0.53219 (14)0.0208 (5)
C210.2499 (2)0.60431 (18)0.61353 (13)0.0195 (5)
C220.3668 (2)0.59741 (18)0.70439 (14)0.0205 (5)
C230.3612 (2)0.68102 (19)0.77832 (14)0.0236 (5)
O230.46807 (18)0.68502 (15)0.86998 (10)0.0329 (4)
C2310.5981 (3)0.6000 (2)0.89170 (16)0.0332 (6)
C240.2401 (3)0.77063 (19)0.76175 (15)0.0275 (5)
C250.1266 (3)0.7769 (2)0.67251 (15)0.0284 (5)
C260.1297 (3)0.69469 (19)0.59773 (15)0.0247 (5)
H120.16620.12540.15420.027*
H130.20430.26600.28160.025*
H150.57810.05840.43610.026*
H160.53330.07330.30280.027*
H170.26440.37810.40180.024*
H270.16990.53050.47090.025*
H220.44930.53610.71540.025*
H23A0.55200.51910.89530.040*
H23B0.67290.61990.95560.040*
H23C0.65980.60180.83930.040*
H240.23610.82750.81250.033*
H250.04470.83860.66180.034*
H260.05050.69980.53610.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0256 (9)0.0214 (10)0.0178 (8)0.0019 (7)0.0020 (7)0.0010 (7)
C120.0264 (11)0.0228 (12)0.0166 (9)0.0010 (9)0.0009 (8)0.0042 (8)
C130.0248 (11)0.0170 (11)0.0192 (9)0.0017 (9)0.0015 (8)0.0012 (8)
C140.0204 (10)0.0166 (11)0.0183 (9)0.0034 (8)0.0041 (8)0.0006 (8)
C150.0212 (10)0.0220 (12)0.0196 (9)0.0007 (9)0.0001 (8)0.0003 (8)
C160.0244 (10)0.0199 (11)0.0222 (10)0.0019 (9)0.0038 (8)0.0002 (8)
C170.0225 (10)0.0175 (11)0.0186 (10)0.0017 (9)0.0031 (8)0.0003 (8)
O10.0381 (9)0.0237 (8)0.0196 (7)0.0059 (7)0.0058 (6)0.0031 (6)
N170.0266 (9)0.0190 (9)0.0130 (8)0.0023 (7)0.0008 (7)0.0023 (7)
N270.0272 (9)0.0172 (9)0.0156 (8)0.0024 (7)0.0048 (7)0.0022 (7)
C270.0260 (10)0.0213 (11)0.0143 (9)0.0008 (9)0.0029 (8)0.0021 (8)
C210.0238 (10)0.0167 (11)0.0196 (10)0.0022 (8)0.0078 (8)0.0012 (8)
C220.0217 (10)0.0198 (11)0.0204 (10)0.0004 (9)0.0059 (8)0.0015 (8)
C230.0247 (11)0.0249 (12)0.0215 (10)0.0023 (9)0.0059 (8)0.0027 (8)
O230.0325 (8)0.0375 (10)0.0245 (8)0.0061 (7)0.0020 (6)0.0129 (7)
C2310.0346 (12)0.0341 (14)0.0255 (11)0.0022 (11)0.0041 (9)0.0074 (10)
C240.0360 (12)0.0220 (12)0.0268 (11)0.0001 (10)0.0119 (9)0.0072 (9)
C250.0337 (12)0.0222 (12)0.0313 (12)0.0057 (10)0.0114 (10)0.0005 (9)
C260.0287 (11)0.0239 (12)0.0211 (10)0.0023 (9)0.0051 (8)0.0049 (8)
Geometric parameters (Å, º) top
N11—C161.337 (2)C27—H270.95
N11—C121.345 (3)C21—C261.394 (3)
C12—C131.386 (3)C21—C221.400 (3)
C12—H120.95C22—C231.389 (3)
C13—C141.389 (3)C22—H220.95
C13—H130.95C23—O231.369 (2)
C14—C151.388 (3)C23—C241.393 (3)
C14—C171.512 (3)O23—C2311.411 (3)
C15—C161.383 (3)C231—H23A0.98
C15—H150.95C231—H23B0.98
C16—H160.95C231—H23C0.98
C17—O11.223 (2)C24—C251.369 (3)
C17—N171.353 (3)C24—H240.95
N17—N271.387 (2)C25—C261.384 (3)
N17—H170.88C25—H250.95
N27—C271.275 (3)C26—H260.95
C27—C211.465 (3)
C16—N11—C12116.92 (16)C26—C21—C22120.04 (18)
N11—C12—C13123.44 (17)C26—C21—C27117.57 (17)
N11—C12—H12118.3C22—C21—C27122.39 (18)
C13—C12—H12118.3C23—C22—C21119.37 (19)
C12—C13—C14119.01 (18)C23—C22—H22120.3
C12—C13—H13120.5C21—C22—H22120.3
C14—C13—H13120.5O23—C23—C22125.37 (18)
C15—C14—C13117.80 (17)O23—C23—C24114.58 (17)
C15—C14—C17117.36 (16)C22—C23—C24120.05 (18)
C13—C14—C17124.80 (18)C23—O23—C231118.28 (15)
C16—C15—C14119.33 (17)O23—C231—H23A109.5
C16—C15—H15120.3O23—C231—H23B109.5
C14—C15—H15120.3H23A—C231—H23B109.5
N11—C16—C15123.47 (19)O23—C231—H23C109.5
N11—C16—H16118.3H23A—C231—H23C109.5
C15—C16—H16118.3H23B—C231—H23C109.5
O1—C17—N17123.21 (17)C25—C24—C23120.17 (19)
O1—C17—C14120.36 (18)C25—C24—H24119.9
N17—C17—C14116.40 (15)C23—C24—H24119.9
C17—N17—N27118.59 (15)C24—C25—C26120.8 (2)
C17—N17—H17120.7C24—C25—H25119.6
N27—N17—H17120.7C26—C25—H25119.6
C27—N27—N17115.28 (15)C25—C26—C21119.53 (19)
N27—C27—C21121.85 (17)C25—C26—H26120.2
N27—C27—H27119.1C21—C26—H26120.2
C21—C27—H27119.1
C16—N11—C12—C130.8 (3)N17—N27—C27—C21179.40 (17)
N11—C12—C13—C141.0 (3)N27—C27—C21—C26177.36 (19)
C12—C13—C14—C152.0 (3)N27—C27—C21—C223.0 (3)
C12—C13—C14—C17175.39 (18)C26—C21—C22—C230.2 (3)
C13—C14—C15—C161.1 (3)C27—C21—C22—C23179.86 (18)
C17—C14—C15—C16176.41 (18)C21—C22—C23—O23179.60 (18)
C12—N11—C16—C151.7 (3)C21—C22—C23—C240.0 (3)
C14—C15—C16—N110.7 (3)C22—C23—O23—C2311.8 (3)
C15—C14—C17—O15.7 (3)C24—C23—O23—C231177.87 (19)
C13—C14—C17—O1171.67 (19)O23—C23—C24—C25179.40 (18)
C15—C14—C17—N17176.09 (18)C22—C23—C24—C250.2 (3)
C13—C14—C17—N176.6 (3)C23—C24—C25—C260.2 (3)
O1—C17—N17—N270.6 (3)C24—C25—C26—C210.0 (3)
C14—C17—N17—N27177.58 (16)C22—C21—C26—C250.3 (3)
C17—N17—N27—C27172.55 (18)C27—C21—C26—C25179.89 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.882.243.044 (2)152
C12—H12···O1ii0.952.403.227 (2)145
C24—H24···N27iii0.952.573.480 (3)161
C27—H27···N11i0.952.583.353 (3)139
C16—H16···Cg2iv0.952.923.689 (2)139
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+3/2; (iv) x+1/2, y+1/2, z1/2.
(XIII) N-isonicotinoyl 4-methoxybenzaldehydehydrazone top
Crystal data top
C14H13N3O2·H2OF(000) = 576
Mr = 273.29Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3002 reflections
a = 7.2702 (2) Åθ = 3.2–27.6°
b = 12.3085 (5) ŵ = 0.10 mm1
c = 14.7299 (6) ÅT = 120 K
β = 97.370 (3)°Plate, colourless
V = 1307.22 (8) Å30.36 × 0.18 × 0.05 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3002 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2550 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 3.2°
ϕ & ω scansh = 99
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1515
Tmin = 0.972, Tmax = 0.995l = 1819
14720 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0518P)2 + 1.3161P]
where P = (Fo2 + 2Fc2)/3
3002 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C14H13N3O2·H2OV = 1307.22 (8) Å3
Mr = 273.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.2702 (2) ŵ = 0.10 mm1
b = 12.3085 (5) ÅT = 120 K
c = 14.7299 (6) Å0.36 × 0.18 × 0.05 mm
β = 97.370 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3002 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2550 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.995Rint = 0.054
14720 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.07Δρmax = 0.55 e Å3
3002 reflectionsΔρmin = 0.26 e Å3
182 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.3674 (2)0.64170 (15)0.00512 (11)0.0273 (4)
C120.4632 (3)0.67382 (16)0.08417 (13)0.0237 (4)
C130.4656 (3)0.61667 (15)0.16551 (13)0.0209 (4)
C140.3664 (3)0.52034 (15)0.16538 (13)0.0207 (4)
C150.2717 (3)0.48411 (17)0.08244 (14)0.0261 (4)
C160.2755 (3)0.54703 (18)0.00512 (14)0.0290 (5)
C170.3516 (3)0.45384 (16)0.24959 (13)0.0210 (4)
O10.3476 (2)0.35389 (11)0.24625 (10)0.0270 (3)
N170.3351 (2)0.51258 (13)0.32488 (10)0.0210 (3)
N270.2966 (2)0.46005 (13)0.40326 (10)0.0215 (3)
C270.2743 (3)0.52519 (16)0.46882 (13)0.0213 (4)
C210.2229 (2)0.48909 (15)0.55672 (12)0.0201 (4)
C220.2154 (3)0.56569 (16)0.62589 (13)0.0219 (4)
C230.1626 (3)0.53758 (16)0.70939 (13)0.0227 (4)
C240.1133 (2)0.43093 (15)0.72535 (12)0.0198 (4)
O240.06597 (19)0.41100 (11)0.81042 (9)0.0239 (3)
C2410.0145 (3)0.30219 (16)0.83091 (13)0.0249 (4)
C250.1180 (3)0.35286 (15)0.65724 (12)0.0206 (4)
C260.1735 (3)0.38237 (15)0.57379 (13)0.0211 (4)
O20.3743 (2)0.74712 (11)0.34021 (9)0.0268 (3)
H120.53320.73900.08460.028*
H130.53400.64300.22040.025*
H150.20570.41730.07930.031*
H160.20980.52210.05090.035*
H170.34850.58360.32440.025*
H270.29200.60070.45990.026*
H220.24740.63900.61520.026*
H230.15990.59090.75580.027*
H24A0.09410.28030.78840.037*
H24B0.01560.29890.89380.037*
H24C0.11800.25290.82450.037*
H250.08350.27990.66770.025*
H260.17780.32890.52760.025*
H2A0.36610.78240.39300.040*
H2B0.46600.77940.31450.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0303 (9)0.0298 (9)0.0225 (8)0.0076 (7)0.0063 (7)0.0018 (7)
C120.0238 (9)0.0211 (9)0.0276 (10)0.0041 (7)0.0080 (7)0.0012 (8)
C130.0208 (9)0.0209 (9)0.0214 (9)0.0029 (7)0.0043 (7)0.0029 (7)
C140.0214 (9)0.0189 (9)0.0222 (9)0.0042 (7)0.0042 (7)0.0018 (7)
C150.0270 (10)0.0235 (10)0.0277 (10)0.0008 (8)0.0036 (8)0.0061 (8)
C160.0305 (10)0.0333 (11)0.0224 (10)0.0042 (9)0.0010 (8)0.0045 (8)
C170.0191 (9)0.0197 (9)0.0251 (9)0.0010 (7)0.0057 (7)0.0001 (7)
O10.0360 (8)0.0159 (7)0.0311 (8)0.0022 (6)0.0118 (6)0.0014 (5)
N170.0266 (8)0.0167 (8)0.0206 (8)0.0005 (6)0.0070 (6)0.0022 (6)
N270.0244 (8)0.0214 (8)0.0189 (8)0.0009 (6)0.0034 (6)0.0026 (6)
C270.0225 (9)0.0184 (9)0.0230 (9)0.0005 (7)0.0034 (7)0.0025 (7)
C210.0184 (8)0.0204 (9)0.0218 (9)0.0031 (7)0.0030 (7)0.0041 (7)
C220.0240 (9)0.0169 (9)0.0247 (9)0.0014 (7)0.0028 (7)0.0030 (7)
C230.0282 (10)0.0188 (9)0.0211 (9)0.0005 (7)0.0034 (7)0.0018 (7)
C240.0208 (9)0.0212 (9)0.0171 (8)0.0015 (7)0.0017 (7)0.0017 (7)
O240.0338 (8)0.0214 (7)0.0175 (6)0.0005 (6)0.0070 (5)0.0010 (5)
C2410.0315 (10)0.0217 (10)0.0226 (9)0.0015 (8)0.0082 (8)0.0038 (7)
C250.0247 (9)0.0163 (9)0.0208 (9)0.0009 (7)0.0026 (7)0.0016 (7)
C260.0263 (9)0.0171 (9)0.0199 (9)0.0029 (7)0.0033 (7)0.0014 (7)
O20.0378 (8)0.0195 (7)0.0249 (7)0.0032 (6)0.0104 (6)0.0018 (5)
Geometric parameters (Å, º) top
N11—C121.338 (3)C21—C261.393 (3)
N11—C161.343 (3)C21—C221.394 (3)
C12—C131.388 (3)C22—C231.379 (3)
C12—H120.95C22—H220.95
C13—C141.388 (3)C23—C241.389 (3)
C13—H130.95C23—H230.95
C14—C151.396 (3)C24—O241.364 (2)
C14—C171.501 (3)C24—C251.393 (3)
C15—C161.381 (3)O24—C2411.433 (2)
C15—H150.95C241—H24A0.98
C16—H160.95C241—H24B0.98
C17—O11.231 (2)C241—H24C0.98
C17—N171.342 (2)C25—C261.390 (3)
N17—N271.383 (2)C25—H250.95
N17—H170.88C26—H260.95
N27—C271.281 (2)O2—H2A0.9001
C27—C211.462 (3)O2—H2B0.90
C27—H270.95
C12—N11—C16117.38 (17)C26—C21—C22118.06 (17)
N11—C12—C13123.32 (19)C26—C21—C27123.20 (17)
N11—C12—H12118.3C22—C21—C27118.69 (17)
C13—C12—H12118.3C23—C22—C21121.58 (18)
C12—C13—C14118.88 (18)C23—C22—H22119.2
C12—C13—H13120.6C21—C22—H22119.2
C14—C13—H13120.6C22—C23—C24119.71 (17)
C13—C14—C15118.16 (18)C22—C23—H23120.1
C13—C14—C17123.84 (17)C24—C23—H23120.1
C15—C14—C17117.98 (17)O24—C24—C23115.25 (16)
C16—C15—C14118.87 (19)O24—C24—C25124.76 (17)
C16—C15—H15120.6C23—C24—C25119.98 (17)
C14—C15—H15120.6C24—O24—C241117.72 (15)
N11—C16—C15123.32 (19)O24—C241—H24A109.5
N11—C16—H16118.3O24—C241—H24B109.5
C15—C16—H16118.3H24A—C241—H24B109.5
O1—C17—N17124.53 (18)O24—C241—H24C109.5
O1—C17—C14121.04 (17)H24A—C241—H24C109.5
N17—C17—C14114.35 (16)H24B—C241—H24C109.5
C17—N17—N27119.16 (16)C26—C25—C24119.55 (17)
C17—N17—H17120.4C26—C25—H25120.2
N27—N17—H17120.4C24—C25—H25120.2
C27—N27—N17113.30 (16)C25—C26—C21121.12 (17)
N27—C27—C21123.29 (18)C25—C26—H26119.4
N27—C27—H27118.4C21—C26—H26119.4
C21—C27—H27118.4H2A—O2—H2B106.6
C16—N11—C12—C132.6 (3)N17—N27—C27—C21176.68 (16)
N11—C12—C13—C141.0 (3)N27—C27—C21—C267.4 (3)
C12—C13—C14—C151.4 (3)N27—C27—C21—C22175.35 (18)
C12—C13—C14—C17177.31 (17)C26—C21—C22—C230.6 (3)
C13—C14—C15—C162.1 (3)C27—C21—C22—C23178.05 (17)
C17—C14—C15—C16176.65 (18)C21—C22—C23—C240.8 (3)
C12—N11—C16—C151.8 (3)C22—C23—C24—O24179.07 (16)
C14—C15—C16—N110.5 (3)C22—C23—C24—C250.2 (3)
C13—C14—C17—O1144.08 (19)C23—C24—O24—C241179.78 (17)
C15—C14—C17—O137.2 (3)C25—C24—O24—C2411.0 (3)
C13—C14—C17—N1738.9 (3)O24—C24—C25—C26178.26 (17)
C15—C14—C17—N17139.85 (18)C23—C24—C25—C260.5 (3)
O1—C17—N17—N275.2 (3)C24—C25—C26—C210.6 (3)
C14—C17—N17—N27171.75 (15)C22—C21—C26—C250.1 (3)
C17—N17—N27—C27176.47 (17)C27—C21—C26—C25177.21 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O20.882.032.907 (2)173
O2—H2A···N11i0.901.902.794 (2)176
O2—H2B···O1ii0.901.952.846 (2)176
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1/2, z+1/2.
(XIV) N-isonicotinoyl 2-ethoxybenzaldehydehydrazone top
Crystal data top
C15H15N3O2F(000) = 1136
Mr = 269.30Dx = 1.310 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6259 reflections
a = 8.3787 (3) Åθ = 2.5–27.5°
b = 18.2450 (7) ŵ = 0.09 mm1
c = 17.8701 (7) ÅT = 120 K
β = 90.975 (2)°Block, colourless
V = 2731.40 (18) Å30.15 × 0.10 × 0.10 mm
Z = 8
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6259 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.101
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.5°
ϕ & ω scansh = 1010
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 2323
Tmin = 0.977, Tmax = 0.991l = 2023
36314 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0646P)2]
where P = (Fo2 + 2Fc2)/3
6259 reflections(Δ/σ)max < 0.001
363 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C15H15N3O2V = 2731.40 (18) Å3
Mr = 269.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.3787 (3) ŵ = 0.09 mm1
b = 18.2450 (7) ÅT = 120 K
c = 17.8701 (7) Å0.15 × 0.10 × 0.10 mm
β = 90.975 (2)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6259 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3252 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.991Rint = 0.101
36314 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å3
6259 reflectionsΔρmin = 0.22 e Å3
363 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.2340 (2)0.47253 (11)0.01027 (11)0.0480 (5)
C120.3231 (3)0.42644 (12)0.02971 (13)0.0438 (6)
C130.4060 (2)0.44493 (11)0.09511 (12)0.0373 (5)
C140.4000 (2)0.51669 (10)0.11968 (12)0.0330 (5)
C150.3099 (2)0.56605 (12)0.07790 (13)0.0436 (6)
C160.2294 (3)0.54137 (13)0.01526 (14)0.0499 (6)
C170.4894 (2)0.54463 (11)0.18730 (12)0.0343 (5)
O10.54021 (16)0.60796 (7)0.18926 (9)0.0445 (4)
N170.50727 (19)0.49675 (8)0.24398 (10)0.0363 (4)
N270.58615 (19)0.51937 (9)0.30882 (10)0.0382 (4)
C270.5863 (2)0.47283 (11)0.36289 (12)0.0370 (5)
C210.6655 (2)0.49102 (11)0.43347 (12)0.0357 (5)
C220.6866 (2)0.43837 (11)0.48994 (12)0.0367 (5)
O220.62164 (15)0.37096 (7)0.47492 (8)0.0407 (4)
C2210.6323 (3)0.31602 (11)0.53255 (13)0.0456 (6)
C2220.5368 (3)0.25150 (12)0.50690 (14)0.0546 (6)
C230.7679 (2)0.45541 (12)0.55578 (13)0.0443 (6)
C240.8252 (3)0.52589 (12)0.56696 (14)0.0512 (6)
C250.8025 (3)0.57936 (12)0.51301 (14)0.0507 (6)
C260.7228 (2)0.56158 (11)0.44731 (13)0.0424 (6)
N310.09225 (19)0.22791 (9)0.41265 (10)0.0406 (4)
C320.0442 (2)0.19013 (11)0.41047 (12)0.0408 (5)
C330.1785 (2)0.21210 (10)0.37276 (11)0.0339 (5)
C340.1738 (2)0.27779 (10)0.33334 (11)0.0296 (5)
C350.0339 (2)0.31774 (10)0.33493 (11)0.0335 (5)
C360.0937 (2)0.29143 (11)0.37458 (12)0.0390 (5)
C370.3104 (2)0.30835 (10)0.28998 (11)0.0315 (5)
O30.31086 (15)0.37316 (7)0.27039 (8)0.0386 (4)
N370.42922 (18)0.26125 (8)0.27497 (9)0.0349 (4)
N470.56225 (19)0.28542 (9)0.23692 (9)0.0360 (4)
C470.6705 (2)0.23622 (11)0.22917 (12)0.0366 (5)
C410.8199 (2)0.25275 (11)0.19229 (12)0.0368 (5)
C420.9413 (2)0.19967 (11)0.19138 (12)0.0388 (5)
O420.91086 (16)0.13473 (7)0.22608 (9)0.0441 (4)
C4211.0376 (2)0.08101 (11)0.22868 (14)0.0459 (6)
C4220.9849 (3)0.01803 (12)0.27611 (14)0.0527 (6)
C431.0867 (2)0.21637 (12)0.15773 (13)0.0452 (6)
C441.1110 (3)0.28414 (13)0.12689 (13)0.0493 (6)
C450.9937 (3)0.33680 (13)0.12764 (12)0.0476 (6)
C460.8488 (2)0.32095 (12)0.15984 (12)0.0418 (5)
H120.33090.37730.01250.053*
H130.46530.40910.12230.045*
H150.30390.61610.09230.052*
H160.16590.57570.01190.060*
H170.45850.45400.24260.044*
H270.53480.42680.35670.044*
H22D0.58970.33540.57990.055*
H22E0.74510.30170.54130.055*
H22A0.57920.23320.45970.082*
H22B0.42520.26610.49940.082*
H22C0.54330.21280.54480.082*
H230.78430.41900.59310.053*
H240.88080.53760.61220.061*
H250.84130.62770.52110.061*
H260.70630.59850.41050.051*
H320.04920.14490.43680.049*
H330.27230.18290.37370.041*
H350.02570.36300.30890.040*
H360.18850.32000.37500.047*
H370.42310.21420.28520.042*
H470.65270.18820.24780.044*
H42D1.13600.10310.25040.055*
H42E1.06090.06370.17750.055*
H42A0.88500.00210.25550.079*
H42B0.96780.03510.32730.079*
H42C1.06730.02010.27650.079*
H431.16890.18050.15630.054*
H441.21050.29490.10460.059*
H451.01200.38370.10620.057*
H460.76740.35720.15990.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0423 (11)0.0586 (13)0.0431 (12)0.0058 (9)0.0050 (9)0.0051 (10)
C120.0447 (12)0.0426 (13)0.0441 (15)0.0035 (11)0.0019 (11)0.0020 (11)
C130.0366 (11)0.0317 (11)0.0437 (15)0.0032 (9)0.0006 (10)0.0013 (10)
C140.0298 (10)0.0311 (11)0.0385 (13)0.0007 (9)0.0104 (9)0.0061 (10)
C150.0471 (13)0.0372 (12)0.0467 (15)0.0069 (10)0.0093 (11)0.0089 (11)
C160.0468 (13)0.0563 (15)0.0467 (16)0.0150 (12)0.0066 (12)0.0174 (13)
C170.0338 (11)0.0285 (11)0.0409 (14)0.0000 (9)0.0103 (9)0.0014 (10)
O10.0522 (9)0.0263 (8)0.0555 (11)0.0073 (7)0.0095 (7)0.0007 (7)
N170.0424 (10)0.0276 (9)0.0389 (11)0.0091 (7)0.0008 (8)0.0028 (8)
N270.0399 (10)0.0385 (10)0.0364 (11)0.0071 (8)0.0036 (8)0.0018 (9)
C270.0336 (11)0.0329 (11)0.0448 (14)0.0029 (9)0.0042 (10)0.0024 (10)
C210.0322 (11)0.0338 (12)0.0413 (14)0.0001 (9)0.0067 (9)0.0032 (10)
C220.0341 (11)0.0328 (12)0.0433 (14)0.0014 (9)0.0038 (10)0.0037 (10)
O220.0461 (8)0.0340 (8)0.0419 (9)0.0028 (6)0.0015 (7)0.0026 (7)
C2210.0502 (13)0.0396 (12)0.0469 (15)0.0009 (11)0.0002 (11)0.0094 (11)
C2220.0564 (14)0.0427 (13)0.0646 (17)0.0060 (12)0.0034 (12)0.0127 (12)
C230.0487 (13)0.0436 (13)0.0404 (15)0.0035 (11)0.0021 (11)0.0001 (11)
C240.0612 (15)0.0464 (14)0.0458 (16)0.0036 (12)0.0063 (12)0.0057 (12)
C250.0624 (15)0.0415 (13)0.0483 (16)0.0092 (11)0.0028 (12)0.0087 (12)
C260.0480 (13)0.0383 (13)0.0412 (15)0.0058 (10)0.0072 (11)0.0017 (10)
N310.0389 (10)0.0396 (10)0.0434 (12)0.0008 (8)0.0053 (8)0.0001 (9)
C320.0470 (13)0.0343 (12)0.0411 (14)0.0035 (10)0.0035 (10)0.0062 (10)
C330.0338 (11)0.0287 (11)0.0392 (13)0.0015 (9)0.0018 (9)0.0000 (9)
C340.0324 (11)0.0254 (10)0.0310 (12)0.0031 (8)0.0029 (9)0.0043 (9)
C350.0386 (11)0.0266 (10)0.0352 (13)0.0007 (9)0.0035 (9)0.0021 (9)
C360.0351 (11)0.0399 (12)0.0420 (14)0.0011 (10)0.0014 (10)0.0090 (10)
C370.0344 (11)0.0273 (11)0.0327 (13)0.0021 (9)0.0043 (9)0.0008 (9)
O30.0402 (8)0.0272 (8)0.0486 (10)0.0036 (6)0.0006 (7)0.0047 (7)
N370.0331 (9)0.0273 (9)0.0444 (11)0.0029 (7)0.0046 (8)0.0043 (8)
N470.0318 (9)0.0379 (10)0.0382 (11)0.0039 (8)0.0020 (8)0.0027 (8)
C470.0370 (11)0.0371 (12)0.0356 (13)0.0025 (9)0.0028 (9)0.0008 (10)
C410.0321 (11)0.0460 (13)0.0322 (13)0.0040 (10)0.0026 (9)0.0056 (10)
C420.0409 (12)0.0377 (12)0.0377 (13)0.0052 (10)0.0010 (10)0.0092 (10)
O420.0363 (8)0.0393 (8)0.0570 (11)0.0014 (6)0.0084 (7)0.0062 (7)
C4210.0363 (12)0.0416 (13)0.0600 (17)0.0022 (10)0.0081 (11)0.0143 (12)
C4220.0486 (14)0.0431 (13)0.0668 (18)0.0032 (11)0.0098 (12)0.0087 (12)
C430.0355 (12)0.0500 (14)0.0504 (16)0.0031 (10)0.0060 (10)0.0162 (12)
C440.0435 (13)0.0609 (16)0.0437 (15)0.0107 (12)0.0108 (11)0.0068 (12)
C450.0447 (13)0.0562 (15)0.0419 (14)0.0108 (12)0.0009 (11)0.0058 (12)
C460.0369 (12)0.0511 (14)0.0374 (13)0.0011 (10)0.0005 (10)0.0021 (11)
Geometric parameters (Å, º) top
N11—C121.326 (3)N31—C321.336 (2)
N11—C161.337 (3)N31—C361.344 (3)
C12—C131.391 (3)C32—C331.381 (3)
C12—H120.95C32—H320.95
C13—C141.382 (3)C33—C341.390 (3)
C13—H130.95C33—H330.95
C14—C151.385 (3)C34—C351.381 (3)
C14—C171.500 (3)C34—C371.500 (3)
C15—C161.373 (3)C35—C361.379 (3)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.232 (2)C37—O31.233 (2)
C17—N171.344 (3)C37—N371.345 (2)
N17—N271.387 (2)N37—N471.387 (2)
N17—H170.8799N37—H370.88
N27—C271.286 (3)N47—C471.285 (2)
C27—C211.454 (3)C47—C411.456 (3)
C27—H270.95C47—H470.95
C21—C261.394 (3)C41—C461.396 (3)
C21—C221.402 (3)C41—C421.405 (3)
C22—O221.369 (2)C42—O421.363 (2)
C22—C231.385 (3)C42—C431.401 (3)
O22—C2211.439 (2)O42—C4211.445 (2)
C221—C2221.491 (3)C421—C4221.499 (3)
C221—H22D0.99C421—H42D0.99
C221—H22E0.99C421—H42E0.99
C222—H22A0.98C422—H42A0.98
C222—H22B0.98C422—H42B0.98
C222—H22C0.98C422—H42C0.98
C23—C241.386 (3)C43—C441.370 (3)
C23—H230.95C43—H430.95
C24—C251.382 (3)C44—C451.375 (3)
C24—H240.95C44—H440.95
C25—C261.380 (3)C45—C461.383 (3)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
C12—N11—C16115.5 (2)C32—N31—C36115.51 (17)
N11—C12—C13124.6 (2)N31—C32—C33124.69 (19)
N11—C12—H12117.7N31—C32—H32117.7
C13—C12—H12117.7C33—C32—H32117.7
C14—C13—C12118.45 (19)C32—C33—C34118.78 (18)
C14—C13—H13120.8C32—C33—H33120.6
C12—C13—H13120.8C34—C33—H33120.6
C13—C14—C15117.8 (2)C35—C34—C33117.45 (18)
C13—C14—C17123.88 (18)C35—C34—C37118.01 (17)
C15—C14—C17118.24 (18)C33—C34—C37124.54 (17)
C16—C15—C14118.8 (2)C36—C35—C34119.53 (19)
C16—C15—H15120.6C36—C35—H35120.2
C14—C15—H15120.6C34—C35—H35120.2
N11—C16—C15124.7 (2)N31—C36—C35124.04 (19)
N11—C16—H16117.6N31—C36—H36118.0
C15—C16—H16117.6C35—C36—H36118.0
O1—C17—N17123.7 (2)O3—C37—N37123.37 (18)
O1—C17—C14120.63 (19)O3—C37—C34120.59 (17)
N17—C17—C14115.72 (17)N37—C37—C34116.04 (16)
C17—N17—N27118.79 (16)C37—N37—N47119.86 (15)
C17—N17—H17120.6C37—N37—H37122.4
N27—N17—H17120.1N47—N37—H37117.5
C27—N27—N17115.17 (17)C47—N47—N37113.90 (16)
N27—C27—C21119.71 (19)N47—C47—C41121.19 (19)
N27—C27—H27120.1N47—C47—H47119.4
C21—C27—H27120.1C41—C47—H47119.4
C26—C21—C22117.8 (2)C46—C41—C42118.64 (19)
C26—C21—C27121.0 (2)C46—C41—C47121.94 (18)
C22—C21—C27121.20 (18)C42—C41—C47119.38 (19)
O22—C22—C23123.8 (2)O42—C42—C43123.71 (19)
O22—C22—C21115.43 (19)O42—C42—C41116.93 (18)
C23—C22—C21120.77 (19)C43—C42—C41119.3 (2)
C22—O22—C221117.74 (16)C42—O42—C421117.44 (16)
O22—C221—C222107.66 (18)O42—C421—C422108.32 (17)
O22—C221—H22D110.2O42—C421—H42D110.0
C222—C221—H22D110.2C422—C421—H42D110.0
O22—C221—H22E110.2O42—C421—H42E110.0
C222—C221—H22E110.2C422—C421—H42E110.0
H22D—C221—H22E108.5H42D—C421—H42E108.4
C221—C222—H22A109.5C421—C422—H42A109.5
C221—C222—H22B109.5C421—C422—H42B109.5
H22A—C222—H22B109.5H42A—C422—H42B109.5
C221—C222—H22C109.5C421—C422—H42C109.5
H22A—C222—H22C109.5H42A—C422—H42C109.5
H22B—C222—H22C109.5H42B—C422—H42C109.5
C22—C23—C24119.7 (2)C44—C43—C42120.3 (2)
C22—C23—H23120.2C44—C43—H43119.8
C24—C23—H23120.2C42—C43—H43119.8
C25—C24—C23120.7 (2)C43—C44—C45121.0 (2)
C25—C24—H24119.6C43—C44—H44119.5
C23—C24—H24119.6C45—C44—H44119.5
C26—C25—C24119.1 (2)C44—C45—C46119.4 (2)
C26—C25—H25120.4C44—C45—H45120.3
C24—C25—H25120.4C46—C45—H45120.3
C25—C26—C21121.9 (2)C45—C46—C41121.3 (2)
C25—C26—H26119.1C45—C46—H46119.4
C21—C26—H26119.1C41—C46—H46119.4
C16—N11—C12—C131.4 (3)C36—N31—C32—C330.1 (3)
N11—C12—C13—C142.0 (3)N31—C32—C33—C340.5 (3)
C12—C13—C14—C150.7 (3)C32—C33—C34—C350.5 (3)
C12—C13—C14—C17177.24 (18)C32—C33—C34—C37179.98 (18)
C13—C14—C15—C161.0 (3)C33—C34—C35—C360.2 (3)
C17—C14—C15—C16179.04 (19)C37—C34—C35—C36179.67 (17)
C12—N11—C16—C150.5 (3)C32—N31—C36—C350.3 (3)
C14—C15—C16—N111.7 (3)C34—C35—C36—N310.3 (3)
C13—C14—C17—O1147.0 (2)C35—C34—C37—O315.4 (3)
C15—C14—C17—O130.9 (3)C33—C34—C37—O3164.00 (18)
C13—C14—C17—N1733.7 (3)C35—C34—C37—N37164.97 (17)
C15—C14—C17—N17148.42 (18)C33—C34—C37—N3715.6 (3)
O1—C17—N17—N270.5 (3)O3—C37—N37—N471.4 (3)
C14—C17—N17—N27178.80 (15)C34—C37—N37—N47178.23 (15)
C17—N17—N27—C27174.10 (17)C37—N37—N47—C47176.85 (18)
N17—N27—C27—C21179.97 (16)N37—N47—C47—C41178.38 (16)
N27—C27—C21—C268.8 (3)N47—C47—C41—C463.9 (3)
N27—C27—C21—C22171.40 (19)N47—C47—C41—C42173.85 (19)
C26—C21—C22—O22177.04 (17)C46—C41—C42—O42177.60 (17)
C27—C21—C22—O222.7 (3)C47—C41—C42—O420.2 (3)
C26—C21—C22—C232.8 (3)C46—C41—C42—C430.4 (3)
C27—C21—C22—C23177.38 (19)C47—C41—C42—C43178.21 (18)
C23—C22—O22—C2213.1 (3)C43—C42—O42—C4210.8 (3)
C21—C22—O22—C221176.78 (17)C41—C42—O42—C421177.06 (18)
C22—O22—C221—C222173.11 (17)C42—O42—C421—C422173.93 (17)
O22—C22—C23—C24177.98 (19)O42—C42—C43—C44177.0 (2)
C21—C22—C23—C241.9 (3)C41—C42—C43—C440.8 (3)
C22—C23—C24—C250.2 (3)C42—C43—C44—C450.6 (3)
C23—C24—C25—C260.5 (4)C43—C44—C45—C460.2 (4)
C24—C25—C26—C210.6 (3)C44—C45—C46—C410.7 (3)
C22—C21—C26—C252.2 (3)C42—C41—C46—C450.4 (3)
C27—C21—C26—C25178.03 (19)C47—C41—C46—C45177.40 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O30.881.992.836 (2)160
N37—H37···O1i0.882.012.879 (2)168
C27—H27···O30.952.603.352 (2)136
C33—H33···O1i0.952.383.238 (2)150
C47—H47···O1i0.952.473.287 (2)145
Symmetry code: (i) x+1, y1/2, z+1/2.
(XV) N-isonicotinoyl 3-ethoxybenzaldehydehydrazone top
Crystal data top
C15H15N3O2F(000) = 568
Mr = 269.30Dx = 1.339 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3089 reflections
a = 24.2060 (17) Åθ = 3.8–27.9°
b = 5.5637 (4) ŵ = 0.09 mm1
c = 9.9571 (4) ÅT = 120 K
β = 94.965 (4)°Block, colourless
V = 1335.94 (14) Å30.10 × 0.04 × 0.03 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3089 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2245 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
Detector resolution: 9.091 pixels mm-1θmax = 27.9°, θmin = 3.8°
ϕ & ω scansh = 3131
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 77
Tmin = 0.985, Tmax = 0.997l = 1212
17209 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1145P)2 + 0.807P]
where P = (Fo2 + 2Fc2)/3
3089 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C15H15N3O2V = 1335.94 (14) Å3
Mr = 269.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 24.2060 (17) ŵ = 0.09 mm1
b = 5.5637 (4) ÅT = 120 K
c = 9.9571 (4) Å0.10 × 0.04 × 0.03 mm
β = 94.965 (4)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3089 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2245 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.997Rint = 0.077
17209 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.09Δρmax = 0.32 e Å3
3089 reflectionsΔρmin = 0.31 e Å3
182 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.46930 (10)1.2555 (4)0.5871 (2)0.0316 (5)
C120.46048 (11)1.0481 (5)0.6480 (2)0.0293 (6)
C130.41829 (11)0.8892 (5)0.6054 (2)0.0279 (6)
C140.38363 (10)0.9450 (5)0.4911 (2)0.0258 (6)
C150.39299 (11)1.1596 (5)0.4255 (3)0.0281 (6)
C160.43558 (12)1.3083 (5)0.4780 (3)0.0312 (6)
C170.33847 (11)0.7834 (5)0.4321 (2)0.0261 (6)
O10.32397 (8)0.7854 (4)0.31090 (17)0.0336 (5)
N170.31707 (9)0.6371 (4)0.5221 (2)0.0280 (5)
N270.27501 (9)0.4788 (4)0.4795 (2)0.0272 (5)
C270.26185 (11)0.3332 (5)0.5710 (3)0.0279 (6)
C210.21697 (11)0.1589 (5)0.5475 (2)0.0261 (6)
C220.17571 (11)0.1870 (5)0.4406 (2)0.0271 (6)
C230.13304 (10)0.0221 (5)0.4250 (2)0.0269 (6)
O230.08936 (7)0.0337 (3)0.32784 (17)0.0318 (5)
C2310.08654 (11)0.2364 (5)0.2386 (3)0.0315 (6)
C2320.03418 (12)0.2120 (6)0.1465 (3)0.0386 (7)
C240.13114 (12)0.1719 (5)0.5139 (3)0.0325 (6)
C250.17197 (12)0.1971 (5)0.6185 (3)0.0321 (6)
C260.21436 (11)0.0312 (5)0.6377 (2)0.0285 (6)
H120.48441.00610.72500.035*
H130.41320.74480.65370.034*
H150.37071.20380.34620.034*
H160.44101.45640.43360.037*
H170.32980.64210.60760.034*
H270.28200.33870.65720.034*
H220.17710.31800.37980.032*
H23B0.11930.23910.18540.038*
H23A0.08590.38770.29080.038*
H23C0.03440.05760.09920.046*
H23D0.03210.34320.08060.046*
H23E0.00200.21930.19980.046*
H240.10190.28570.50230.039*
H250.17090.33030.67790.039*
H260.24150.04670.71200.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0315 (13)0.0344 (13)0.0280 (11)0.0030 (10)0.0012 (9)0.0044 (9)
C120.0275 (14)0.0358 (15)0.0234 (12)0.0019 (11)0.0041 (10)0.0023 (10)
C130.0270 (14)0.0283 (13)0.0283 (13)0.0009 (11)0.0008 (10)0.0002 (10)
C140.0203 (13)0.0311 (14)0.0257 (12)0.0033 (10)0.0001 (9)0.0046 (10)
C150.0252 (14)0.0323 (14)0.0259 (12)0.0030 (11)0.0032 (10)0.0004 (10)
C160.0335 (15)0.0309 (14)0.0288 (13)0.0011 (12)0.0006 (11)0.0015 (11)
C170.0217 (13)0.0299 (14)0.0261 (13)0.0022 (11)0.0011 (10)0.0006 (10)
O10.0327 (11)0.0428 (11)0.0242 (9)0.0096 (9)0.0041 (7)0.0007 (8)
N170.0227 (11)0.0318 (12)0.0282 (11)0.0026 (9)0.0049 (8)0.0017 (9)
N270.0212 (11)0.0313 (12)0.0282 (11)0.0033 (9)0.0031 (8)0.0053 (9)
C270.0221 (13)0.0313 (14)0.0296 (13)0.0003 (11)0.0018 (10)0.0011 (10)
C210.0206 (13)0.0271 (13)0.0303 (13)0.0024 (10)0.0003 (10)0.0016 (10)
C220.0257 (14)0.0280 (13)0.0271 (13)0.0008 (11)0.0002 (10)0.0007 (10)
C230.0226 (13)0.0333 (14)0.0242 (12)0.0000 (11)0.0005 (9)0.0029 (10)
O230.0263 (10)0.0393 (11)0.0285 (10)0.0069 (8)0.0042 (7)0.0004 (8)
C2310.0255 (14)0.0369 (15)0.0314 (14)0.0012 (12)0.0019 (10)0.0012 (11)
C2320.0286 (15)0.0482 (18)0.0375 (16)0.0035 (13)0.0060 (12)0.0006 (13)
C240.0340 (16)0.0272 (14)0.0364 (14)0.0052 (12)0.0029 (11)0.0023 (11)
C250.0329 (15)0.0265 (13)0.0367 (14)0.0030 (11)0.0015 (11)0.0023 (11)
C260.0272 (14)0.0298 (14)0.0278 (13)0.0032 (11)0.0020 (10)0.0009 (10)
Geometric parameters (Å, º) top
N11—C121.329 (4)C21—C261.393 (4)
N11—C161.334 (3)C21—C221.403 (3)
C12—C131.389 (4)C22—C231.380 (4)
C12—H120.95C22—H220.95
C13—C141.390 (3)C23—O231.371 (3)
C13—H130.95C23—C241.399 (4)
C14—C151.389 (4)O23—C2311.434 (3)
C14—C171.496 (4)C231—C2321.505 (4)
C15—C161.388 (4)C231—H23B0.99
C15—H150.95C231—H23A0.99
C16—H160.95C232—H23C0.98
C17—O11.227 (3)C232—H23D0.98
C17—N171.347 (3)C232—H23E0.98
N17—N271.385 (3)C24—C251.379 (4)
N17—H170.88C24—H240.95
N27—C271.280 (3)C25—C261.381 (4)
C27—C211.460 (4)C25—H250.95
C27—H270.95C26—H260.95
C12—N11—C16116.8 (2)C23—C22—C21119.2 (2)
N11—C12—C13123.8 (2)C23—C22—H22120.4
N11—C12—H12118.1C21—C22—H22120.4
C13—C12—H12118.1O23—C23—C22124.9 (2)
C12—C13—C14118.9 (2)O23—C23—C24114.7 (2)
C12—C13—H13120.5C22—C23—C24120.4 (2)
C14—C13—H13120.5C23—O23—C231117.8 (2)
C15—C14—C13117.8 (2)O23—C231—C232107.4 (2)
C15—C14—C17118.4 (2)O23—C231—H23B110.2
C13—C14—C17123.8 (2)C232—C231—H23B110.2
C16—C15—C14118.7 (2)O23—C231—H23A110.2
C16—C15—H15120.6C232—C231—H23A110.2
C14—C15—H15120.6H23B—C231—H23A108.5
N11—C16—C15123.9 (3)C231—C232—H23C109.5
N11—C16—H16118.0C231—C232—H23D109.5
C15—C16—H16118.0H23C—C232—H23D109.5
O1—C17—N17124.5 (2)C231—C232—H23E109.5
O1—C17—C14121.2 (2)H23C—C232—H23E109.5
N17—C17—C14114.3 (2)H23D—C232—H23E109.5
C17—N17—N27119.7 (2)C25—C24—C23119.7 (3)
C17—N17—H17120.2C25—C24—H24120.1
N27—N17—H17120.2C23—C24—H24120.1
C27—N27—N17113.9 (2)C24—C25—C26120.8 (3)
N27—C27—C21122.2 (2)C24—C25—H25119.6
N27—C27—H27118.9C26—C25—H25119.6
C21—C27—H27118.9C25—C26—C21119.5 (2)
C26—C21—C22120.3 (2)C25—C26—H26120.2
C26—C21—C27118.4 (2)C21—C26—H26120.2
C22—C21—C27121.2 (2)
C16—N11—C12—C131.0 (4)N27—C27—C21—C26163.7 (3)
N11—C12—C13—C141.4 (4)N27—C27—C21—C2219.4 (4)
C12—C13—C14—C150.4 (4)C26—C21—C22—C230.9 (4)
C12—C13—C14—C17177.2 (2)C27—C21—C22—C23177.8 (2)
C13—C14—C15—C161.0 (4)C21—C22—C23—O23177.7 (2)
C17—C14—C15—C16178.7 (2)C21—C22—C23—C240.5 (4)
C12—N11—C16—C150.5 (4)C22—C23—O23—C2312.4 (4)
C14—C15—C16—N111.5 (4)C24—C23—O23—C231176.0 (2)
C15—C14—C17—O126.8 (4)C23—O23—C231—C232177.7 (2)
C13—C14—C17—O1150.8 (3)O23—C23—C24—C25177.9 (2)
C15—C14—C17—N17154.6 (2)C22—C23—C24—C250.5 (4)
C13—C14—C17—N1727.8 (4)C23—C24—C25—C260.9 (4)
O1—C17—N17—N271.3 (4)C24—C25—C26—C212.4 (4)
C14—C17—N17—N27179.9 (2)C22—C21—C26—C252.4 (4)
C17—N17—N27—C27173.5 (2)C27—C21—C26—C25179.3 (2)
N17—N27—C27—C21177.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O1i0.882.082.898 (3)154
C12—H12···N11ii0.952.523.424 (3)160
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y1/2, z+3/2.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC13H11N3OC13H10FN3OC13H10FN3OC13H10FN3O·H2O
Mr225.25243.24243.24261.26
Crystal system, space groupOrthorhombic, PbcaTriclinic, P1Orthorhombic, PbcaOrthorhombic, P212121
Temperature (K)120120120120
a, b, c (Å)7.1927 (2), 21.2168 (7), 28.6771 (10)7.4815 (2), 11.1344 (2), 14.5365 (3)13.1910 (4), 18.8057 (6), 18.2843 (4)6.4189 (3), 6.8520 (3), 27.3451 (12)
α, β, γ (°)90, 90, 9090.663 (2), 104.903 (3), 109.268 (2)90, 90, 9090, 90, 90
V3)4376.3 (2)1098.45 (5)4535.7 (2)1202.70 (9)
Z164164
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.110.110.11
Crystal size (mm)0.50 × 0.25 × 0.200.36 × 0.04 × 0.020.12 × 0.06 × 0.040.48 × 0.38 × 0.22
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.966, 0.9820.969, 0.9980.975, 0.9960.960, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
24117, 4964, 3331 24858, 5044, 3443 32649, 5207, 3977 8595, 1630, 1412
Rint0.0500.0580.0710.031
(sin θ/λ)max1)0.6500.6500.6520.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.05 0.053, 0.125, 1.03 0.063, 0.151, 1.10 0.034, 0.088, 1.03
No. of reflections4964504452071630
No. of parameters308325336176
No. of restraints0001
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0763P)2]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2769P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0684P)2 + 1.9661P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.050P)2 + 0.2601P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.42, 0.480.23, 0.310.67, 0.660.21, 0.20
Absolute structure???Friedel pairs merged


(V)(VI)(VIII)(IX)
Crystal data
Chemical formulaC13H10ClN3OC13H10ClN3OC13H10BrN3OC13H10BrN3O
Mr259.69259.69304.15304.15
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/nMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)120120120120
a, b, c (Å)7.9977 (2), 6.7184 (2), 22.5514 (6)7.4524 (3), 11.2367 (4), 14.3949 (3)8.0268 (2), 6.7134 (3), 22.5024 (10)7.4578 (2), 11.3264 (3), 14.3558 (3)
α, β, γ (°)90, 98.609 (3), 9090, 102.701 (2), 9090, 99.297 (3), 9090, 101.119 (2), 90
V3)1198.07 (6)1175.94 (7)1196.66 (8)1189.87 (5)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.310.323.433.45
Crystal size (mm)0.40 × 0.14 × 0.020.34 × 0.28 × 0.180.12 × 0.03 × 0.020.40 × 0.20 × 0.02
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.893, 0.9940.886, 0.9460.654, 0.9350.340, 0.934
No. of measured, independent and
observed [I > 2σ(I)] reflections
18325, 2757, 2159 15675, 2691, 2076 11911, 2746, 2182 14830, 2733, 2231
Rint0.0420.0340.0620.043
(sin θ/λ)max1)0.6500.6490.6530.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.03 0.038, 0.143, 1.08 0.041, 0.093, 1.06 0.028, 0.073, 1.07
No. of reflections2757269127462733
No. of parameters163163163164
No. of restraints0000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0486P)2 + 0.4843P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0972P)2 + 0.0157P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0225P)2 + 1.7209P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0343P)2 + 0.5661P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.31, 0.290.38, 0.330.45, 0.580.41, 0.55
Absolute structure????


(X)(XI)(XII)(XIII)
Crystal data
Chemical formulaC13H10BrN3O·H2OC14H13N3O2C14H13N3O2C14H13N3O2·H2O
Mr322.17255.27255.27273.29
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)120120120120
a, b, c (Å)14.2570 (3), 14.6299 (4), 14.1669 (4)9.8899 (3), 15.8189 (4), 17.0380 (5)8.2938 (4), 11.0771 (6), 13.846 (5)7.2702 (2), 12.3085 (5), 14.7299 (6)
α, β, γ (°)90, 119.152 (2), 9090, 97.236 (2), 9090, 103.478 (3), 9090, 97.370 (3), 90
V3)2580.61 (12)2644.32 (13)1237.0 (5)1307.22 (8)
Z8844
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)3.190.090.100.10
Crystal size (mm)0.38 × 0.24 × 0.240.40 × 0.08 × 0.050.15 × 0.15 × 0.040.36 × 0.18 × 0.05
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.341, 0.4650.974, 0.9960.977, 0.9960.972, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
28990, 5916, 5220 33120, 6048, 4196 14906, 2827, 1776 14720, 3002, 2550
Rint0.0450.0530.0580.054
(sin θ/λ)max1)0.6510.6500.6490.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.157, 1.23 0.052, 0.106, 1.02 0.047, 0.162, 1.09 0.057, 0.142, 1.07
No. of reflections5916604828273002
No. of parameters344345173182
No. of restraints0000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.017P)2 + 24.843P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0411P)2 + 0.7605P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0889P)2]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0518P)2 + 1.3161P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)2.26, 0.730.19, 0.220.28, 0.330.55, 0.26
Absolute structure????


(XIV)(XV)
Crystal data
Chemical formulaC15H15N3O2C15H15N3O2
Mr269.30269.30
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)120120
a, b, c (Å)8.3787 (3), 18.2450 (7), 17.8701 (7)24.2060 (17), 5.5637 (4), 9.9571 (4)
α, β, γ (°)90, 90.975 (2), 9090, 94.965 (4), 90
V3)2731.40 (18)1335.94 (14)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.15 × 0.10 × 0.100.10 × 0.04 × 0.03
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.977, 0.9910.985, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
36314, 6259, 3252 17209, 3089, 2245
Rint0.1010.077
(sin θ/λ)max1)0.6500.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.137, 1.00 0.069, 0.221, 1.09
No. of reflections62593089
No. of parameters363182
No. of restraints00
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0646P)2]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.1145P)2 + 0.807P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.20, 0.220.32, 0.31
Absolute structure??

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) & COLLECT, DENZO & COLLECT, OSCAIL (McArdle, 2003) & SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 & PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (XII) top
D—H···AD—HH···AD···AD—H···A
N17—H17···N11i0.882.243.044 (2)152
C12—H12···O1ii0.952.403.227 (2)145
C24—H24···N27iii0.952.573.480 (3)161
C27—H27···N11i0.952.583.353 (3)139
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+3/2.
 

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