Supramolecular structures in N-isonicotinoyl arylaldehydehydrazones: multiple hydrogen-bonding modes in series of geometric isomers

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.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

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

In full text version

(I) N-isonicotinoyl benzaldehydehydrazone

Crystal data

C13H11N3O	F(000) = 1888
Mr = 225.25	Dx = 1.367 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4964 reflections
a = 7.1927 (2) Å	θ = 3.4–27.5°
b = 21.2168 (7) Å	µ = 0.09 mm^−1
c = 28.6771 (10) Å	T = 120 K
V = 4376.3 (2) Å^3	Block, colourless
Z = 16	0.50 × 0.25 × 0.20 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	4964 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ϕ & ω scans	h = −9→5
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −27→27
Tmin = 0.966, Tmax = 0.982	l = −34→37
24117 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0763P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4964 reflections	Δρmax = 0.42 e Å^−3
308 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.30732 (18)	0.89156 (6)	0.36805 (5)	0.0218 (3)
C12	0.2246 (2)	0.83490 (7)	0.36854 (6)	0.0215 (4)
C13	0.2290 (2)	0.79380 (7)	0.40621 (6)	0.0213 (4)
C14	0.3232 (2)	0.81130 (7)	0.44618 (6)	0.0185 (4)
C15	0.4038 (2)	0.87097 (7)	0.44693 (6)	0.0211 (4)
C16	0.3932 (2)	0.90872 (8)	0.40765 (6)	0.0221 (4)
C17	0.3434 (2)	0.77007 (7)	0.48849 (6)	0.0215 (4)
O1	0.36608 (18)	0.79234 (5)	0.52721 (4)	0.0316 (3)
N17	0.33990 (19)	0.70717 (6)	0.47865 (5)	0.0215 (3)
N27	0.34698 (18)	0.66458 (6)	0.51498 (5)	0.0216 (3)
C27	0.3407 (2)	0.60626 (7)	0.50285 (6)	0.0208 (4)
C21	0.3361 (2)	0.55639 (7)	0.53793 (6)	0.0195 (4)
C22	0.2853 (2)	0.49525 (7)	0.52464 (6)	0.0235 (4)
C23	0.2727 (2)	0.44764 (7)	0.55815 (6)	0.0255 (4)
C24	0.3081 (2)	0.46062 (7)	0.60447 (7)	0.0252 (4)
C25	0.3610 (2)	0.52110 (7)	0.61772 (7)	0.0262 (4)
C26	0.3759 (2)	0.56842 (7)	0.58466 (6)	0.0232 (4)
N31	0.27932 (19)	0.64135 (6)	0.38413 (5)	0.0230 (3)
C32	0.1632 (2)	0.59217 (7)	0.38168 (6)	0.0217 (4)
C33	0.1536 (2)	0.55171 (7)	0.34394 (6)	0.0197 (4)
C34	0.2726 (2)	0.56107 (7)	0.30643 (6)	0.0189 (4)
C35	0.3915 (2)	0.61300 (7)	0.30806 (6)	0.0230 (4)
C36	0.3888 (2)	0.65142 (7)	0.34690 (6)	0.0234 (4)
C37	0.2776 (2)	0.51940 (7)	0.26428 (6)	0.0214 (4)
O3	0.31675 (18)	0.54004 (5)	0.22580 (4)	0.0296 (3)
N37	0.23655 (19)	0.45787 (6)	0.27330 (5)	0.0213 (3)
N47	0.24051 (18)	0.41517 (6)	0.23713 (5)	0.0216 (3)
C47	0.1826 (2)	0.35949 (7)	0.24720 (6)	0.0202 (4)
C41	0.1828 (2)	0.30983 (7)	0.21188 (6)	0.0201 (4)
C42	0.1062 (2)	0.25101 (8)	0.22278 (6)	0.0242 (4)
C43	0.0967 (2)	0.20405 (7)	0.18906 (7)	0.0266 (4)
C44	0.1613 (2)	0.21547 (7)	0.14450 (6)	0.0238 (4)
C45	0.2408 (2)	0.27344 (7)	0.13361 (6)	0.0230 (4)
C46	0.2536 (2)	0.31989 (7)	0.16711 (6)	0.0209 (4)
H12	0.1590	0.8221	0.3414	0.026*
H13	0.1680	0.7542	0.4045	0.026*
H15	0.4654	0.8856	0.4741	0.025*
H16	0.4499	0.9491	0.4088	0.027*
H17	0.3333	0.6940	0.4496	0.026*
H27	0.3390	0.5955	0.4707	0.025*
H22	0.2595	0.4861	0.4929	0.028*
H23	0.2396	0.4061	0.5490	0.031*
H24	0.2964	0.4284	0.6272	0.030*
H25	0.3871	0.5300	0.6495	0.031*
H26	0.4135	0.6095	0.5939	0.028*
H32	0.0828	0.5846	0.4074	0.026*
H33	0.0668	0.5180	0.3437	0.024*
H35	0.4732	0.6218	0.2828	0.028*
H36	0.4689	0.6870	0.3473	0.028*
H37	0.2080	0.4456	0.3017	0.026*
H47	0.1393	0.3506	0.2778	0.024*
H42	0.0605	0.2432	0.2533	0.029*
H43	0.0456	0.1641	0.1967	0.032*
H44	0.1515	0.1837	0.1213	0.029*
H45	0.2863	0.2810	0.1030	0.028*
H46	0.3108	0.3590	0.1597	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0231 (8)	0.0229 (7)	0.0195 (8)	0.0018 (5)	0.0016 (6)	0.0019 (6)
C12	0.0235 (9)	0.0235 (8)	0.0176 (9)	0.0007 (6)	−0.0030 (7)	−0.0008 (7)
C13	0.0218 (9)	0.0201 (8)	0.0221 (10)	−0.0003 (6)	−0.0006 (7)	−0.0010 (7)
C14	0.0205 (9)	0.0178 (7)	0.0170 (9)	0.0025 (6)	0.0015 (7)	0.0009 (7)
C15	0.0224 (9)	0.0208 (8)	0.0201 (10)	−0.0013 (6)	−0.0016 (7)	−0.0016 (7)
C16	0.0240 (9)	0.0206 (8)	0.0218 (10)	−0.0021 (6)	0.0003 (7)	0.0009 (7)
C17	0.0242 (9)	0.0206 (8)	0.0196 (10)	−0.0012 (6)	−0.0004 (7)	0.0002 (7)
O1	0.0527 (8)	0.0231 (6)	0.0188 (7)	−0.0014 (5)	−0.0032 (6)	−0.0007 (5)
N17	0.0307 (8)	0.0182 (7)	0.0156 (8)	−0.0004 (6)	−0.0012 (6)	0.0022 (6)
N27	0.0264 (8)	0.0189 (7)	0.0195 (8)	−0.0010 (5)	0.0000 (6)	0.0036 (6)
C27	0.0235 (9)	0.0212 (8)	0.0176 (9)	0.0019 (6)	−0.0003 (7)	−0.0007 (7)
C21	0.0177 (8)	0.0199 (8)	0.0211 (10)	0.0019 (6)	0.0032 (7)	0.0003 (7)
C22	0.0285 (10)	0.0205 (8)	0.0217 (10)	0.0004 (6)	0.0006 (7)	−0.0023 (7)
C23	0.0282 (10)	0.0185 (8)	0.0297 (11)	0.0000 (6)	0.0036 (8)	0.0004 (7)
C24	0.0250 (9)	0.0219 (8)	0.0287 (11)	0.0030 (6)	−0.0002 (8)	0.0078 (8)
C25	0.0310 (10)	0.0257 (9)	0.0220 (10)	0.0023 (7)	−0.0050 (8)	0.0028 (8)
C26	0.0274 (9)	0.0195 (8)	0.0226 (10)	−0.0001 (6)	−0.0043 (7)	0.0003 (7)
N31	0.0275 (8)	0.0203 (7)	0.0211 (8)	0.0006 (5)	−0.0034 (6)	−0.0022 (6)
C32	0.0250 (9)	0.0207 (8)	0.0193 (9)	0.0000 (6)	0.0017 (7)	0.0007 (7)
C33	0.0237 (9)	0.0172 (7)	0.0182 (9)	−0.0001 (6)	−0.0010 (7)	0.0010 (7)
C34	0.0213 (9)	0.0171 (7)	0.0183 (9)	0.0027 (6)	−0.0019 (7)	0.0012 (7)
C35	0.0249 (9)	0.0211 (8)	0.0231 (10)	−0.0010 (6)	0.0036 (7)	0.0032 (7)
C36	0.0251 (9)	0.0193 (8)	0.0257 (10)	−0.0030 (6)	−0.0024 (7)	−0.0009 (7)
C37	0.0237 (9)	0.0205 (8)	0.0199 (10)	0.0016 (6)	0.0002 (7)	−0.0016 (7)
O3	0.0447 (8)	0.0259 (6)	0.0182 (7)	−0.0034 (5)	0.0062 (6)	0.0009 (5)
N37	0.0305 (8)	0.0179 (7)	0.0154 (8)	−0.0009 (5)	0.0021 (6)	−0.0020 (6)
N47	0.0274 (8)	0.0206 (7)	0.0168 (8)	0.0014 (5)	0.0005 (6)	−0.0045 (6)
C47	0.0233 (9)	0.0229 (8)	0.0144 (9)	−0.0001 (6)	−0.0026 (7)	−0.0007 (7)
C41	0.0200 (9)	0.0200 (8)	0.0203 (10)	0.0023 (6)	−0.0039 (7)	−0.0011 (7)
C42	0.0298 (9)	0.0234 (8)	0.0193 (10)	−0.0024 (7)	−0.0013 (7)	0.0025 (7)
C43	0.0315 (10)	0.0189 (8)	0.0294 (11)	−0.0046 (7)	−0.0017 (8)	−0.0002 (8)
C44	0.0258 (9)	0.0212 (8)	0.0243 (10)	0.0031 (6)	−0.0033 (7)	−0.0047 (7)
C45	0.0236 (9)	0.0249 (8)	0.0205 (10)	0.0038 (6)	0.0021 (7)	−0.0012 (7)
C46	0.0222 (9)	0.0193 (8)	0.0213 (10)	−0.0004 (6)	−0.0001 (7)	0.0011 (7)

Geometric parameters (Å, º)

N11—C12	1.341 (2)	N31—C32	1.338 (2)
N11—C16	1.343 (2)	N31—C36	1.344 (2)
C12—C13	1.389 (2)	C32—C33	1.383 (2)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.382 (2)	C33—C34	1.389 (2)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.392 (2)	C34—C35	1.396 (2)
C14—C17	1.503 (2)	C34—C37	1.498 (2)
C15—C16	1.384 (2)	C35—C36	1.380 (2)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O1	1.218 (2)	C37—O3	1.220 (2)
C17—N17	1.3642 (19)	C37—N37	1.3632 (19)
N17—N27	1.3800 (18)	N37—N47	1.3776 (18)
N17—H17	0.88	N37—H37	0.88
N27—C27	1.2862 (19)	N47—C47	1.2857 (19)
C27—C21	1.460 (2)	C47—C41	1.462 (2)
C27—H27	0.95	C47—H47	0.95
C21—C26	1.394 (2)	C41—C46	1.397 (2)
C21—C22	1.401 (2)	C41—C42	1.400 (2)
C22—C23	1.397 (2)	C42—C43	1.390 (2)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.380 (2)	C43—C44	1.381 (2)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.391 (2)	C44—C45	1.392 (2)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.385 (2)	C45—C46	1.379 (2)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C12—N11—C16	115.97 (14)	C32—N31—C36	116.61 (15)
N11—C12—C13	124.12 (16)	N31—C32—C33	123.79 (16)
N11—C12—H12	117.9	N31—C32—H32	118.1
C13—C12—H12	117.9	C33—C32—H32	118.1
C14—C13—C12	119.18 (15)	C32—C33—C34	119.12 (15)
C14—C13—H13	120.4	C32—C33—H33	120.4
C12—C13—H13	120.4	C34—C33—H33	120.4
C13—C14—C15	117.46 (15)	C33—C34—C35	117.68 (15)
C13—C14—C17	124.08 (14)	C33—C34—C37	123.75 (14)
C15—C14—C17	118.46 (15)	C35—C34—C37	118.56 (15)
C16—C15—C14	119.37 (16)	C36—C35—C34	118.97 (16)
C16—C15—H15	120.3	C36—C35—H35	120.5
C14—C15—H15	120.3	C34—C35—H35	120.5
N11—C16—C15	123.83 (15)	N31—C36—C35	123.76 (15)
N11—C16—H16	118.1	N31—C36—H36	118.1
C15—C16—H16	118.1	C35—C36—H36	118.1
O1—C17—N17	124.78 (16)	O3—C37—N37	124.42 (16)
O1—C17—C14	121.55 (14)	O3—C37—C34	121.58 (14)
N17—C17—C14	113.63 (15)	N37—C37—C34	114.00 (15)
C17—N17—N27	118.94 (14)	C37—N37—N47	118.84 (14)
C17—N17—H17	120.5	C37—N37—H37	120.6
N27—N17—H17	120.5	N47—N37—H37	120.6
C27—N27—N17	115.13 (14)	C47—N47—N37	115.36 (14)
N27—C27—C21	120.77 (16)	N47—C47—C41	120.41 (16)
N27—C27—H27	119.6	N47—C47—H47	119.8
C21—C27—H27	119.6	C41—C47—H47	119.8
C26—C21—C22	118.99 (15)	C46—C41—C42	119.00 (15)
C26—C21—C27	121.68 (14)	C46—C41—C47	121.81 (14)
C22—C21—C27	119.30 (16)	C42—C41—C47	119.17 (16)
C23—C22—C21	119.95 (17)	C43—C42—C41	120.19 (16)
C23—C22—H22	120.0	C43—C42—H42	119.9
C21—C22—H22	120.0	C41—C42—H42	119.9
C24—C23—C22	120.38 (16)	C44—C43—C42	120.09 (15)
C24—C23—H23	119.8	C44—C43—H43	120.0
C22—C23—H23	119.8	C42—C43—H43	120.0
C23—C24—C25	119.82 (16)	C43—C44—C45	120.06 (16)
C23—C24—H24	120.1	C43—C44—H44	120.0
C25—C24—H24	120.1	C45—C44—H44	120.0
C26—C25—C24	120.18 (17)	C46—C45—C44	120.17 (17)
C26—C25—H25	119.9	C46—C45—H45	119.9
C24—C25—H25	119.9	C44—C45—H45	119.9
C25—C26—C21	120.64 (15)	C45—C46—C41	120.43 (15)
C25—C26—H26	119.7	C45—C46—H46	119.8
C21—C26—H26	119.7	C41—C46—H46	119.8
C16—N11—C12—C13	−2.2 (2)	C36—N31—C32—C33	1.2 (2)
N11—C12—C13—C14	0.1 (2)	N31—C32—C33—C34	1.3 (2)
C12—C13—C14—C15	2.3 (2)	C32—C33—C34—C35	−2.6 (2)
C12—C13—C14—C17	−177.77 (15)	C32—C33—C34—C37	178.51 (15)
C13—C14—C15—C16	−2.6 (2)	C33—C34—C35—C36	1.5 (2)
C17—C14—C15—C16	177.45 (15)	C37—C34—C35—C36	−179.56 (15)
C12—N11—C16—C15	1.8 (2)	C32—N31—C36—C35	−2.4 (2)
C14—C15—C16—N11	0.5 (3)	C34—C35—C36—N31	1.1 (3)
C13—C14—C17—O1	−153.73 (16)	C33—C34—C37—O3	148.38 (16)
C15—C14—C17—O1	26.2 (2)	C35—C34—C37—O3	−30.5 (2)
C13—C14—C17—N17	28.4 (2)	C33—C34—C37—N37	−32.1 (2)
C15—C14—C17—N17	−151.70 (15)	C35—C34—C37—N37	149.01 (15)
O1—C17—N17—N27	5.7 (2)	O3—C37—N37—N47	0.7 (2)
C14—C17—N17—N27	−176.49 (13)	C34—C37—N37—N47	−178.82 (13)
C17—N17—N27—C27	179.14 (14)	C37—N37—N47—C47	−173.36 (14)
N17—N27—C27—C21	−176.42 (13)	N37—N47—C47—C41	−179.05 (13)
N27—C27—C21—C26	−13.2 (2)	N47—C47—C41—C46	3.2 (2)
N27—C27—C21—C22	164.93 (15)	N47—C47—C41—C42	−175.26 (15)
C26—C21—C22—C23	0.9 (2)	C46—C41—C42—C43	−1.6 (2)
C27—C21—C22—C23	−177.30 (15)	C47—C41—C42—C43	176.86 (14)
C21—C22—C23—C24	0.7 (2)	C41—C42—C43—C44	−0.6 (3)
C22—C23—C24—C25	−1.6 (2)	C42—C43—C44—C45	1.8 (3)
C23—C24—C25—C26	0.8 (2)	C43—C44—C45—C46	−0.6 (3)
C24—C25—C26—C21	0.7 (2)	C44—C45—C46—C41	−1.6 (2)
C22—C21—C26—C25	−1.6 (2)	C42—C41—C46—C45	2.7 (2)
C27—C21—C26—C25	176.53 (15)	C47—C41—C46—C45	−175.71 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N31	0.88	2.22	3.080 (2)	166
N37—H37···N11^i	0.88	2.22	3.076 (2)	163
C12—H12···Cg1^ii	0.95	2.77	3.517 (2)	137
C16—H16···Cg2^iii	0.95	2.89	3.610 (2)	134
C26—H26···Cg3^iii	0.95	2.99	3.581 (2)	121
C43—H43···Cg4^iv	0.95	2.89	3.610 (2)	134

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, −z+1; (iv) −x, y−1/2, −z+1/2.

(II) N-isonicotinoyl 2-fluorobenzaldehydehydrazone

Crystal data

C13H10FN3O	Z = 4
Mr = 243.24	F(000) = 504
Triclinic, P1	Dx = 1.471 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4815 (2) Å	Cell parameters from 5044 reflections
b = 11.1344 (2) Å	θ = 1.5–27.5°
c = 14.5365 (3) Å	µ = 0.11 mm^−1
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) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	5044 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3443 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.5°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.969, Tmax = 0.998	l = −18→18
24858 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 0.2769P] where P = (Fo^2 + 2Fc^2)/3
5044 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.2568 (2)	0.10175 (13)	0.23246 (9)	0.0220 (3)
C12	0.2461 (3)	0.21827 (16)	0.22005 (12)	0.0229 (4)
C13	0.2556 (2)	0.30368 (15)	0.29254 (11)	0.0205 (4)
C14	0.2742 (2)	0.26714 (14)	0.38461 (11)	0.0170 (3)
C15	0.2839 (3)	0.14643 (15)	0.39850 (11)	0.0220 (4)
C16	0.2752 (3)	0.06825 (16)	0.32166 (12)	0.0233 (4)
C17	0.2846 (2)	0.34777 (15)	0.47089 (11)	0.0185 (3)
O1	0.3187 (2)	0.31077 (11)	0.55034 (8)	0.0287 (3)
N17	0.2520 (2)	0.45985 (12)	0.45519 (9)	0.0187 (3)
N27	0.2615 (2)	0.53571 (13)	0.53311 (9)	0.0200 (3)
C27	0.2206 (2)	0.63712 (15)	0.51473 (11)	0.0209 (4)
C21	0.2277 (2)	0.72362 (15)	0.59302 (11)	0.0196 (4)
C22	0.2171 (3)	0.84367 (16)	0.57814 (12)	0.0240 (4)
F22	0.20023 (18)	0.87950 (10)	0.48760 (7)	0.0388 (3)
C23	0.2258 (3)	0.93012 (16)	0.64940 (13)	0.0283 (4)
C24	0.2436 (3)	0.89412 (17)	0.74086 (13)	0.0265 (4)
C25	0.2523 (3)	0.77371 (16)	0.75936 (12)	0.0252 (4)
C26	0.2447 (2)	0.68958 (15)	0.68671 (11)	0.0209 (4)
N31	0.1828 (2)	0.59474 (13)	0.27155 (10)	0.0232 (3)
C32	0.3068 (2)	0.71541 (15)	0.28034 (11)	0.0211 (4)
C33	0.3042 (2)	0.79405 (15)	0.20699 (11)	0.0190 (3)
C34	0.1675 (2)	0.74530 (15)	0.11893 (11)	0.0182 (3)
C35	0.0398 (2)	0.61985 (15)	0.10813 (11)	0.0205 (4)
C36	0.0519 (3)	0.54914 (16)	0.18554 (12)	0.0232 (4)
C37	0.1565 (2)	0.81756 (15)	0.03206 (11)	0.0198 (4)
O3	0.08845 (19)	0.76039 (11)	−0.04838 (8)	0.0289 (3)
N37	0.2310 (2)	0.94722 (12)	0.05026 (9)	0.0206 (3)
N47	0.2291 (2)	1.01832 (12)	−0.02739 (9)	0.0213 (3)
C47	0.3226 (2)	1.13827 (15)	−0.00777 (11)	0.0203 (4)
C41	0.3254 (2)	1.22065 (15)	−0.08559 (11)	0.0193 (4)
C42	0.4632 (3)	1.34337 (15)	−0.07278 (11)	0.0215 (4)
F42	0.59329 (15)	1.38642 (9)	0.01540 (7)	0.0303 (3)
C43	0.4784 (3)	1.42250 (16)	−0.14464 (12)	0.0251 (4)
C44	0.3500 (3)	1.37705 (16)	−0.23482 (12)	0.0262 (4)
C45	0.2069 (3)	1.25612 (16)	−0.25095 (12)	0.0246 (4)
C46	0.1936 (3)	1.17945 (16)	−0.17695 (11)	0.0211 (4)
H12	0.2310	0.2441	0.1573	0.027*
H13	0.2495	0.3859	0.2796	0.025*
H15	0.2965	0.1175	0.4603	0.026*
H16	0.2828	−0.0141	0.3328	0.028*
H17	0.2247	0.4847	0.3960	0.022*
H27	0.1858	0.6562	0.4504	0.025*
H23	0.2198	1.0122	0.6358	0.034*
H24	0.2500	0.9517	0.7913	0.032*
H25	0.2635	0.7491	0.8224	0.030*
H26	0.2510	0.6076	0.7003	0.025*
H32	0.4020	0.7491	0.3402	0.025*
H33	0.3941	0.8795	0.2169	0.023*
H35	−0.0544	0.5832	0.0485	0.025*
H36	−0.0372	0.4637	0.1775	0.028*
H37	0.2568	0.9871	0.1089	0.025*
H47	0.3897	1.1738	0.0566	0.024*
H43	0.5744	1.5060	−0.1326	0.030*
H44	0.3599	1.4289	−0.2860	0.031*
H45	0.1180	1.2259	−0.3128	0.029*
H46	0.0934	1.0976	−0.1883	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0218 (8)	0.0223 (7)	0.0203 (7)	0.0065 (6)	0.0048 (6)	−0.0025 (6)
C12	0.0262 (9)	0.0259 (9)	0.0178 (8)	0.0114 (7)	0.0049 (7)	0.0011 (6)
C13	0.0237 (9)	0.0203 (8)	0.0192 (8)	0.0110 (7)	0.0043 (7)	0.0017 (6)
C14	0.0153 (8)	0.0168 (8)	0.0178 (8)	0.0050 (6)	0.0035 (6)	0.0000 (6)
C15	0.0277 (9)	0.0192 (8)	0.0187 (8)	0.0073 (7)	0.0065 (7)	0.0015 (6)
C16	0.0265 (9)	0.0178 (8)	0.0250 (9)	0.0071 (7)	0.0068 (7)	0.0019 (7)
C17	0.0182 (8)	0.0193 (8)	0.0165 (8)	0.0055 (7)	0.0036 (6)	0.0005 (6)
O1	0.0455 (8)	0.0269 (6)	0.0167 (6)	0.0176 (6)	0.0069 (5)	0.0029 (5)
N17	0.0235 (8)	0.0179 (7)	0.0144 (6)	0.0075 (6)	0.0042 (5)	−0.0002 (5)
N27	0.0214 (7)	0.0190 (7)	0.0183 (7)	0.0053 (6)	0.0057 (6)	−0.0028 (5)
C27	0.0230 (9)	0.0215 (8)	0.0182 (8)	0.0071 (7)	0.0067 (7)	0.0020 (6)
C21	0.0189 (8)	0.0184 (8)	0.0209 (8)	0.0055 (7)	0.0059 (7)	−0.0003 (6)
C22	0.0267 (9)	0.0231 (9)	0.0225 (9)	0.0084 (7)	0.0075 (7)	0.0046 (7)
F22	0.0656 (8)	0.0267 (6)	0.0310 (6)	0.0210 (6)	0.0180 (6)	0.0113 (4)
C23	0.0283 (10)	0.0184 (8)	0.0393 (11)	0.0090 (8)	0.0102 (8)	−0.0017 (7)
C24	0.0205 (9)	0.0265 (9)	0.0295 (9)	0.0052 (7)	0.0063 (7)	−0.0091 (7)
C25	0.0223 (9)	0.0280 (9)	0.0216 (9)	0.0044 (7)	0.0056 (7)	−0.0043 (7)
C26	0.0209 (9)	0.0200 (8)	0.0218 (8)	0.0064 (7)	0.0067 (7)	0.0018 (6)
N31	0.0299 (8)	0.0214 (7)	0.0217 (7)	0.0114 (6)	0.0094 (6)	0.0041 (6)
C32	0.0239 (9)	0.0237 (8)	0.0173 (8)	0.0113 (7)	0.0046 (7)	0.0008 (6)
C33	0.0210 (9)	0.0168 (8)	0.0199 (8)	0.0069 (7)	0.0066 (7)	0.0010 (6)
C34	0.0218 (9)	0.0197 (8)	0.0173 (8)	0.0107 (7)	0.0077 (7)	0.0020 (6)
C35	0.0224 (9)	0.0211 (8)	0.0183 (8)	0.0085 (7)	0.0051 (7)	−0.0002 (6)
C36	0.0260 (9)	0.0193 (8)	0.0242 (9)	0.0058 (7)	0.0096 (7)	0.0016 (6)
C37	0.0229 (9)	0.0219 (8)	0.0172 (8)	0.0102 (7)	0.0067 (7)	0.0029 (6)
O3	0.0441 (8)	0.0234 (6)	0.0164 (6)	0.0109 (6)	0.0047 (5)	0.0003 (5)
N37	0.0308 (8)	0.0185 (7)	0.0135 (7)	0.0093 (6)	0.0064 (6)	0.0027 (5)
N47	0.0285 (8)	0.0217 (7)	0.0171 (7)	0.0115 (6)	0.0081 (6)	0.0059 (5)
C47	0.0232 (9)	0.0224 (9)	0.0172 (8)	0.0097 (7)	0.0066 (7)	0.0013 (6)
C41	0.0249 (9)	0.0188 (8)	0.0196 (8)	0.0114 (7)	0.0100 (7)	0.0021 (6)
C42	0.0244 (9)	0.0219 (8)	0.0203 (8)	0.0102 (7)	0.0074 (7)	−0.0014 (6)
F42	0.0336 (6)	0.0260 (5)	0.0246 (5)	0.0047 (5)	0.0042 (4)	−0.0031 (4)
C43	0.0321 (10)	0.0172 (8)	0.0328 (10)	0.0103 (7)	0.0180 (8)	0.0038 (7)
C44	0.0386 (11)	0.0248 (9)	0.0273 (9)	0.0193 (8)	0.0184 (8)	0.0099 (7)
C45	0.0306 (10)	0.0294 (9)	0.0203 (8)	0.0180 (8)	0.0083 (7)	0.0050 (7)
C46	0.0249 (9)	0.0204 (8)	0.0226 (8)	0.0121 (7)	0.0087 (7)	0.0024 (6)

Geometric parameters (Å, º)

N11—C12	1.337 (2)	N31—C32	1.340 (2)
N11—C16	1.339 (2)	N31—C36	1.345 (2)
C12—C13	1.383 (2)	C32—C33	1.388 (2)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.389 (2)	C33—C34	1.387 (2)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.384 (2)	C34—C35	1.388 (2)
C14—C17	1.504 (2)	C34—C37	1.504 (2)
C15—C16	1.383 (2)	C35—C36	1.382 (2)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O1	1.2238 (19)	C37—O3	1.2225 (19)
C17—N17	1.359 (2)	C37—N37	1.360 (2)
N17—N27	1.3779 (19)	N37—N47	1.3859 (17)
N17—H17	0.8998	N37—H37	0.90
N27—C27	1.278 (2)	N47—C47	1.275 (2)
C27—C21	1.461 (2)	C47—C41	1.465 (2)
C27—H27	0.95	C47—H47	0.95
C21—C22	1.381 (2)	C41—C42	1.389 (2)
C21—C26	1.403 (2)	C41—C46	1.400 (2)
C22—F22	1.3665 (19)	C42—F42	1.3626 (19)
C22—C23	1.380 (2)	C42—C43	1.377 (2)
C23—C24	1.379 (3)	C43—C44	1.383 (2)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.389 (3)	C44—C45	1.388 (2)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.381 (2)	C45—C46	1.384 (2)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C12—N11—C16	116.00 (14)	C32—N31—C36	116.74 (14)
N11—C12—C13	124.35 (15)	N31—C32—C33	123.75 (15)
N11—C12—H12	117.8	N31—C32—H32	118.1
C13—C12—H12	117.8	C33—C32—H32	118.1
C12—C13—C14	118.84 (15)	C34—C33—C32	118.59 (14)
C12—C13—H13	120.6	C34—C33—H33	120.7
C14—C13—H13	120.6	C32—C33—H33	120.7
C15—C14—C13	117.52 (15)	C33—C34—C35	118.43 (14)
C15—C14—C17	116.98 (14)	C33—C34—C37	123.97 (14)
C13—C14—C17	125.50 (14)	C35—C34—C37	117.50 (14)
C16—C15—C14	119.43 (15)	C36—C35—C34	118.91 (15)
C16—C15—H15	120.3	C36—C35—H35	120.5
C14—C15—H15	120.3	C34—C35—H35	120.5
N11—C16—C15	123.85 (15)	N31—C36—C35	123.57 (15)
N11—C16—H16	118.1	N31—C36—H36	118.2
C15—C16—H16	118.1	C35—C36—H36	118.2
O1—C17—N17	123.09 (14)	O3—C37—N37	123.96 (14)
O1—C17—C14	120.08 (14)	O3—C37—C34	120.59 (14)
N17—C17—C14	116.83 (13)	N37—C37—C34	115.43 (13)
C17—N17—N27	117.96 (13)	C37—N37—N47	117.72 (13)
C17—N17—H17	121.8	C37—N37—H37	122.0
N27—N17—H17	120.2	N47—N37—H37	119.0
C27—N27—N17	115.93 (13)	C47—N47—N37	115.75 (13)
N27—C27—C21	119.73 (15)	N47—C47—C41	119.25 (14)
N27—C27—H27	120.1	N47—C47—H47	120.4
C21—C27—H27	120.1	C41—C47—H47	120.4
C22—C21—C26	116.48 (15)	C42—C41—C46	116.52 (14)
C22—C21—C27	121.34 (15)	C42—C41—C47	121.32 (15)
C26—C21—C27	122.18 (15)	C46—C41—C47	122.14 (15)
F22—C22—C23	118.17 (15)	F42—C42—C43	118.33 (14)
F22—C22—C21	117.85 (15)	F42—C42—C41	117.95 (14)
C23—C22—C21	123.97 (16)	C43—C42—C41	123.71 (15)
C24—C23—C22	118.17 (16)	C42—C43—C44	118.20 (15)
C24—C23—H23	120.9	C42—C43—H43	120.9
C22—C23—H23	120.9	C44—C43—H43	120.9
C23—C24—C25	120.11 (16)	C43—C44—C45	120.37 (15)
C23—C24—H24	119.9	C43—C44—H44	119.8
C25—C24—H24	119.9	C45—C44—H44	119.8
C26—C25—C24	120.40 (16)	C46—C45—C44	120.08 (16)
C26—C25—H25	119.8	C46—C45—H45	120.0
C24—C25—H25	119.8	C44—C45—H45	120.0
C25—C26—C21	120.86 (16)	C45—C46—C41	121.07 (15)
C25—C26—H26	119.6	C45—C46—H46	119.5
C21—C26—H26	119.6	C41—C46—H46	119.5
C16—N11—C12—C13	0.9 (3)	C36—N31—C32—C33	1.0 (3)
N11—C12—C13—C14	−1.1 (3)	N31—C32—C33—C34	−0.8 (3)
C12—C13—C14—C15	0.5 (2)	C32—C33—C34—C35	−0.2 (2)
C12—C13—C14—C17	−179.41 (15)	C32—C33—C34—C37	−176.37 (16)
C13—C14—C15—C16	0.1 (2)	C33—C34—C35—C36	0.8 (2)
C17—C14—C15—C16	−179.94 (15)	C37—C34—C35—C36	177.30 (15)
C12—N11—C16—C15	−0.2 (2)	C32—N31—C36—C35	−0.3 (3)
C14—C15—C16—N11	−0.3 (3)	C34—C35—C36—N31	−0.7 (3)
C15—C14—C17—O1	6.6 (2)	C33—C34—C37—O3	153.48 (17)
C13—C14—C17—O1	−173.48 (16)	C35—C34—C37—O3	−22.8 (2)
C15—C14—C17—N17	−172.52 (15)	C33—C34—C37—N37	−24.9 (2)
C13—C14—C17—N17	7.4 (2)	C35—C34—C37—N37	158.88 (15)
O1—C17—N17—N27	1.2 (2)	O3—C37—N37—N47	0.1 (3)
C14—C17—N17—N27	−179.74 (13)	C34—C37—N37—N47	178.37 (14)
C17—N17—N27—C27	−176.75 (14)	C37—N37—N47—C47	−171.32 (15)
N17—N27—C27—C21	−179.75 (14)	N37—N47—C47—C41	−179.08 (14)
N27—C27—C21—C22	169.03 (16)	N47—C47—C41—C42	−163.00 (16)
N27—C27—C21—C26	−11.2 (3)	N47—C47—C41—C46	15.4 (3)
C26—C21—C22—F22	−179.89 (15)	C46—C41—C42—F42	179.85 (14)
C27—C21—C22—F22	−0.1 (2)	C47—C41—C42—F42	−1.6 (2)
C26—C21—C22—C23	1.2 (3)	C46—C41—C42—C43	−1.7 (3)
C27—C21—C22—C23	−179.05 (16)	C47—C41—C42—C43	176.82 (16)
F22—C22—C23—C24	−179.77 (15)	F42—C42—C43—C44	178.04 (15)
C21—C22—C23—C24	−0.9 (3)	C41—C42—C43—C44	−0.4 (3)
C22—C23—C24—C25	0.0 (3)	C42—C43—C44—C45	1.7 (3)
C23—C24—C25—C26	0.5 (3)	C43—C44—C45—C46	−0.9 (3)
C24—C25—C26—C21	−0.1 (3)	C44—C45—C46—C41	−1.3 (3)
C22—C21—C26—C25	−0.7 (2)	C42—C41—C46—C45	2.6 (2)
C27—C21—C26—C25	179.58 (16)	C47—C41—C46—C45	−175.96 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N31	0.90	2.21	3.0895 (19)	165
N37—H37···N11^i	0.90	2.19	3.0700 (19)	165
C13—H13···N31	0.95	2.53	3.463 (2)	167

Symmetry code: (i) x, y+1, z.

(III) N-isonicotinoyl 3-fluorobenzaldehydehydrazone

Crystal data

C13H10FN3O	F(000) = 2016
Mr = 243.24	Dx = 1.425 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5207 reflections
a = 13.1910 (4) Å	θ = 2.9–27.6°
b = 18.8057 (6) Å	µ = 0.11 mm^−1
c = 18.2843 (4) Å	T = 120 K
V = 4535.7 (2) Å^3	Needle, colourless
Z = 16	0.12 × 0.06 × 0.04 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	5207 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ϕ & ω scans	h = −14→17
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −24→21
Tmin = 0.975, Tmax = 0.996	l = −22→23
32649 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 1.9661P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
5207 reflections	Δρmax = 0.67 e Å^−3
336 parameters	Δρmin = −0.66 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0206 (14)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.48911 (13)	−0.04000 (9)	0.36595 (10)	0.0271 (4)
C12	0.40080 (15)	−0.00579 (10)	0.37487 (11)	0.0246 (4)
C13	0.39033 (14)	0.05825 (10)	0.41165 (11)	0.0233 (4)
C14	0.47641 (14)	0.08952 (10)	0.44133 (10)	0.0222 (4)
C15	0.56870 (14)	0.05504 (10)	0.43207 (11)	0.0244 (4)
C16	0.57108 (15)	−0.00894 (11)	0.39506 (12)	0.0266 (4)
C17	0.47670 (14)	0.15832 (10)	0.48285 (11)	0.0234 (4)
O1	0.55367 (11)	0.19416 (8)	0.48815 (8)	0.0322 (4)
N17	0.38765 (12)	0.17658 (8)	0.51417 (9)	0.0237 (4)
N27	0.38387 (12)	0.23581 (8)	0.55838 (9)	0.0233 (4)
C37	0.11594 (14)	0.11515 (10)	0.51004 (11)	0.0221 (4)
C27	0.29804 (14)	0.24726 (10)	0.58816 (11)	0.0236 (4)
C21	0.28062 (14)	0.30477 (10)	0.64067 (11)	0.0229 (4)
C22	0.18202 (14)	0.31315 (11)	0.66708 (11)	0.0253 (4)
C23	0.16399 (14)	0.36499 (11)	0.71864 (11)	0.0256 (4)
F23	0.06787 (9)	0.37216 (7)	0.74408 (8)	0.0397 (4)
C24	0.23791 (15)	0.40892 (11)	0.74548 (11)	0.0270 (4)
C25	0.33552 (15)	0.40023 (11)	0.71901 (12)	0.0274 (5)
C26	0.35741 (15)	0.34884 (11)	0.66716 (11)	0.0259 (4)
N31	−0.14132 (13)	0.02314 (9)	0.61911 (10)	0.0290 (4)
C32	−0.15375 (16)	0.06896 (12)	0.56491 (13)	0.0327 (5)
C33	−0.07478 (16)	0.10133 (12)	0.52769 (13)	0.0323 (5)
C34	0.02389 (14)	0.08595 (10)	0.54775 (11)	0.0221 (4)
C35	0.03770 (16)	0.03871 (12)	0.60450 (13)	0.0342 (5)
C36	−0.04620 (17)	0.00940 (13)	0.63802 (14)	0.0391 (6)
O3	0.20099 (10)	0.09197 (7)	0.52349 (8)	0.0281 (3)
N37	0.09777 (12)	0.16686 (8)	0.46035 (9)	0.0240 (4)
N47	0.17787 (12)	0.19446 (9)	0.42072 (9)	0.0251 (4)
C47	0.15322 (15)	0.24611 (10)	0.37845 (11)	0.0247 (4)
C41	0.22817 (15)	0.28149 (10)	0.33232 (11)	0.0257 (4)
C42	0.32939 (16)	0.26093 (12)	0.33128 (12)	0.0315 (5)
C43	0.39533 (17)	0.29646 (13)	0.28605 (13)	0.0364 (5)
F43	0.49092 (15)	0.27994 (12)	0.28543 (14)	0.0521 (8)	0.652 (4)
C44	0.36606 (16)	0.35160 (11)	0.24134 (12)	0.0323 (5)
C45	0.26565 (17)	0.37122 (11)	0.24312 (13)	0.0334 (5)
F45	0.2425 (3)	0.4250 (2)	0.2084 (2)	0.0431 (13)	0.348 (4)
C46	0.19610 (16)	0.33746 (10)	0.28778 (12)	0.0273 (4)
H12	0.3416	−0.0268	0.3547	0.029*
H13	0.3258	0.0802	0.4164	0.028*
H15	0.6293	0.0752	0.4509	0.029*
H16	0.6346	−0.0323	0.3899	0.032*
H17	0.3328	0.1510	0.5064	0.028*
H27	0.2429	0.2171	0.5757	0.028*
H22	0.1286	0.2837	0.6499	0.030*
H24	0.2228	0.4442	0.7811	0.032*
H25	0.3883	0.4300	0.7367	0.033*
H26	0.4248	0.3436	0.6496	0.031*
H32	−0.2211	0.0804	0.5506	0.039*
H33	−0.0882	0.1336	0.4889	0.039*
H35	0.1041	0.0265	0.6203	0.041*
H36	−0.0351	−0.0228	0.6773	0.047*
H37	0.0358	0.1827	0.4533	0.029*
H47	0.0847	0.2617	0.3771	0.030*
H42	0.3525	0.2230	0.3613	0.038*
H43	0.4645	0.2823	0.2856	0.044*	0.348 (4)
H44	0.4133	0.3752	0.2105	0.039*
H45	0.2434	0.4091	0.2127	0.040*	0.652 (4)
H46	0.1272	0.3522	0.2882	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0283 (9)	0.0255 (8)	0.0274 (9)	0.0014 (7)	0.0046 (7)	−0.0028 (7)
C12	0.0237 (10)	0.0273 (10)	0.0227 (10)	−0.0017 (8)	0.0021 (7)	−0.0024 (8)
C13	0.0223 (9)	0.0257 (10)	0.0218 (10)	0.0027 (7)	0.0031 (7)	−0.0007 (8)
C14	0.0252 (10)	0.0233 (9)	0.0180 (9)	−0.0008 (7)	0.0036 (7)	0.0012 (8)
C15	0.0229 (10)	0.0272 (10)	0.0230 (10)	−0.0014 (8)	0.0010 (7)	0.0003 (8)
C16	0.0245 (10)	0.0270 (10)	0.0284 (11)	0.0046 (8)	0.0041 (8)	0.0006 (9)
C17	0.0261 (10)	0.0235 (9)	0.0206 (10)	0.0014 (8)	0.0013 (7)	0.0008 (8)
O1	0.0282 (8)	0.0326 (8)	0.0359 (9)	−0.0075 (6)	0.0069 (6)	−0.0101 (7)
N17	0.0233 (8)	0.0236 (8)	0.0242 (9)	−0.0006 (6)	0.0018 (6)	−0.0046 (7)
N27	0.0276 (8)	0.0219 (8)	0.0205 (8)	0.0024 (6)	0.0002 (6)	−0.0018 (7)
C37	0.0223 (9)	0.0208 (9)	0.0233 (10)	−0.0015 (7)	0.0024 (7)	−0.0042 (8)
C27	0.0246 (9)	0.0239 (9)	0.0222 (10)	−0.0010 (8)	0.0011 (7)	−0.0008 (8)
C21	0.0256 (10)	0.0236 (9)	0.0195 (10)	0.0020 (7)	0.0026 (7)	0.0018 (8)
C22	0.0231 (10)	0.0276 (10)	0.0251 (11)	−0.0007 (8)	−0.0007 (8)	0.0012 (8)
C23	0.0216 (10)	0.0299 (10)	0.0252 (10)	0.0039 (8)	0.0036 (8)	0.0006 (9)
F23	0.0236 (6)	0.0493 (8)	0.0463 (8)	0.0015 (5)	0.0092 (5)	−0.0168 (7)
C24	0.0315 (11)	0.0258 (10)	0.0235 (11)	0.0030 (8)	0.0018 (8)	−0.0040 (8)
C25	0.0262 (10)	0.0281 (10)	0.0280 (11)	−0.0035 (8)	0.0014 (8)	−0.0054 (9)
C26	0.0219 (9)	0.0290 (10)	0.0269 (11)	0.0004 (8)	0.0047 (8)	−0.0013 (9)
N31	0.0247 (9)	0.0302 (9)	0.0323 (10)	−0.0033 (7)	0.0031 (7)	0.0048 (8)
C32	0.0222 (10)	0.0386 (12)	0.0371 (12)	−0.0005 (9)	0.0015 (9)	0.0102 (10)
C33	0.0269 (11)	0.0369 (11)	0.0330 (12)	0.0000 (9)	0.0022 (9)	0.0130 (10)
C34	0.0231 (10)	0.0198 (9)	0.0234 (10)	−0.0013 (7)	0.0023 (7)	−0.0027 (8)
C35	0.0236 (10)	0.0415 (12)	0.0374 (13)	−0.0020 (9)	−0.0026 (9)	0.0116 (10)
C36	0.0300 (11)	0.0462 (13)	0.0412 (14)	−0.0024 (10)	0.0000 (10)	0.0208 (11)
O3	0.0221 (7)	0.0285 (7)	0.0338 (8)	0.0000 (6)	0.0028 (6)	0.0025 (6)
N37	0.0200 (8)	0.0245 (8)	0.0276 (9)	0.0000 (6)	0.0061 (6)	0.0018 (7)
N47	0.0249 (9)	0.0257 (8)	0.0248 (9)	−0.0044 (7)	0.0075 (7)	−0.0009 (7)
C47	0.0252 (10)	0.0249 (9)	0.0241 (10)	−0.0025 (8)	0.0028 (8)	−0.0029 (9)
C41	0.0298 (10)	0.0263 (10)	0.0211 (10)	−0.0054 (8)	0.0035 (8)	−0.0038 (8)
C42	0.0305 (11)	0.0342 (11)	0.0299 (12)	−0.0027 (9)	0.0043 (8)	0.0072 (9)
C43	0.0298 (11)	0.0410 (13)	0.0384 (13)	−0.0034 (9)	0.0079 (9)	0.0034 (11)
F43	0.0229 (11)	0.0590 (15)	0.0746 (18)	0.0091 (9)	0.0176 (10)	0.0325 (13)
C44	0.0350 (12)	0.0296 (11)	0.0322 (12)	−0.0077 (9)	0.0104 (9)	0.0025 (9)
C45	0.0416 (13)	0.0239 (11)	0.0348 (12)	−0.0039 (9)	0.0075 (10)	0.0012 (10)
F45	0.041 (2)	0.039 (2)	0.050 (3)	0.0038 (17)	0.0045 (18)	0.0235 (19)
C46	0.0295 (10)	0.0239 (10)	0.0286 (11)	−0.0030 (8)	0.0036 (8)	−0.0019 (9)

Geometric parameters (Å, º)

N11—C16	1.339 (3)	C25—H25	0.95
N11—C12	1.341 (2)	C26—H26	0.95
C12—C13	1.386 (3)	N31—C32	1.323 (3)
C12—H12	0.95	N31—C36	1.327 (3)
C13—C14	1.389 (3)	C32—C33	1.385 (3)
C13—H13	0.95	C32—H32	0.95
C14—C15	1.390 (3)	C33—C34	1.383 (3)
C14—C17	1.500 (3)	C33—H33	0.95
C15—C16	1.381 (3)	C34—C35	1.378 (3)
C15—H15	0.95	C35—C36	1.380 (3)
C16—H16	0.95	C35—H35	0.95
C17—O1	1.223 (2)	C36—H36	0.95
C17—N17	1.351 (2)	N37—N47	1.382 (2)
N17—N27	1.377 (2)	N37—H37	0.88
N17—H17	0.88	N47—C47	1.283 (3)
N27—C27	1.275 (2)	C47—C41	1.460 (3)
C37—O3	1.228 (2)	C47—H47	0.95
C37—N37	1.352 (3)	C41—C42	1.390 (3)
C37—C34	1.500 (3)	C41—C46	1.396 (3)
C27—C21	1.464 (3)	C42—C43	1.374 (3)
C27—H27	0.95	C42—H42	0.95
C21—C26	1.396 (3)	C43—F43	1.299 (3)
C21—C22	1.396 (3)	C43—C44	1.376 (3)
C22—C23	1.377 (3)	C43—H43	0.95
C22—H22	0.95	C44—C45	1.375 (3)
C23—F23	1.357 (2)	C44—H44	0.95
C23—C24	1.369 (3)	C45—F45	1.232 (4)
C24—C25	1.385 (3)	C45—C46	1.383 (3)
C24—H24	0.95	C45—H45	0.95
C25—C26	1.384 (3)	C46—H46	0.95
C16—N11—C12	116.36 (17)	C21—C26—H26	120.0
N11—C12—C13	124.22 (18)	C32—N31—C36	116.05 (18)
N11—C12—H12	117.9	N31—C32—C33	124.1 (2)
C13—C12—H12	117.9	N31—C32—H32	117.9
C12—C13—C14	118.42 (17)	C33—C32—H32	117.9
C12—C13—H13	120.8	C34—C33—C32	119.05 (19)
C14—C13—H13	120.8	C34—C33—H33	120.5
C13—C14—C15	118.10 (17)	C32—C33—H33	120.5
C13—C14—C17	124.39 (17)	C35—C34—C33	117.32 (18)
C15—C14—C17	117.51 (17)	C35—C34—C37	118.36 (17)
C16—C15—C14	119.09 (18)	C33—C34—C37	124.28 (18)
C16—C15—H15	120.5	C34—C35—C36	119.1 (2)
C14—C15—H15	120.5	C34—C35—H35	120.5
N11—C16—C15	123.81 (18)	C36—C35—H35	120.5
N11—C16—H16	118.1	N31—C36—C35	124.4 (2)
C15—C16—H16	118.1	N31—C36—H36	117.8
O1—C17—N17	123.25 (18)	C35—C36—H36	117.8
O1—C17—C14	121.18 (17)	C37—N37—N47	119.12 (16)
N17—C17—C14	115.56 (16)	C37—N37—H37	120.4
C17—N17—N27	119.07 (16)	N47—N37—H37	120.4
C17—N17—H17	120.5	C47—N47—N37	113.97 (16)
N27—N17—H17	120.5	N47—C47—C41	121.42 (18)
C27—N27—N17	114.80 (16)	N47—C47—H47	119.3
O3—C37—N37	123.47 (17)	C41—C47—H47	119.3
O3—C37—C34	121.14 (17)	C42—C41—C46	119.51 (19)
N37—C37—C34	115.37 (16)	C42—C41—C47	122.11 (19)
N27—C27—C21	122.97 (18)	C46—C41—C47	118.38 (18)
N27—C27—H27	118.5	C43—C42—C41	118.8 (2)
C21—C27—H27	118.5	C43—C42—H42	120.6
C26—C21—C22	119.28 (18)	C41—C42—H42	120.6
C26—C21—C27	123.52 (17)	F43—C43—C42	120.2 (2)
C22—C21—C27	117.15 (17)	F43—C43—C44	116.6 (2)
C23—C22—C21	118.53 (18)	C42—C43—C44	123.1 (2)
C23—C22—H22	120.7	C42—C43—H43	118.4
C21—C22—H22	120.7	C44—C43—H43	118.4
F23—C23—C24	118.85 (18)	C45—C44—C43	117.29 (19)
F23—C23—C22	117.80 (17)	C45—C44—H44	121.4
C24—C23—C22	123.35 (18)	C43—C44—H44	121.4
C23—C24—C25	117.76 (19)	F45—C45—C44	116.5 (3)
C23—C24—H24	121.1	F45—C45—C46	121.1 (3)
C25—C24—H24	121.1	C44—C45—C46	122.0 (2)
C26—C25—C24	121.03 (19)	C44—C45—H45	119.0
C26—C25—H25	119.5	C46—C45—H45	119.0
C24—C25—H25	119.5	C45—C46—C41	119.3 (2)
C25—C26—C21	120.06 (18)	C45—C46—H46	120.3
C25—C26—H26	120.0	C41—C46—H46	120.3
C16—N11—C12—C13	0.0 (3)	N31—C32—C33—C34	−0.4 (4)
N11—C12—C13—C14	0.1 (3)	C32—C33—C34—C35	−0.1 (3)
C12—C13—C14—C15	0.4 (3)	C32—C33—C34—C37	177.51 (19)
C12—C13—C14—C17	−179.63 (18)	O3—C37—C34—C35	8.0 (3)
C13—C14—C15—C16	−1.0 (3)	N37—C37—C34—C35	−173.12 (19)
C17—C14—C15—C16	179.07 (18)	O3—C37—C34—C33	−169.6 (2)
C12—N11—C16—C15	−0.6 (3)	N37—C37—C34—C33	9.3 (3)
C14—C15—C16—N11	1.1 (3)	C33—C34—C35—C36	0.1 (3)
C13—C14—C17—O1	−157.19 (19)	C37—C34—C35—C36	−177.7 (2)
C15—C14—C17—O1	22.7 (3)	C32—N31—C36—C35	−0.9 (4)
C13—C14—C17—N17	23.8 (3)	C34—C35—C36—N31	0.5 (4)
C15—C14—C17—N17	−156.28 (18)	O3—C37—N37—N47	1.8 (3)
O1—C17—N17—N27	−4.5 (3)	C34—C37—N37—N47	−177.11 (16)
C14—C17—N17—N27	174.52 (16)	C37—N37—N47—C47	−175.96 (17)
C17—N17—N27—C27	−177.04 (18)	N37—N47—C47—C41	−179.77 (17)
N17—N27—C27—C21	175.89 (17)	N47—C47—C41—C42	0.5 (3)
N27—C27—C21—C26	−5.0 (3)	N47—C47—C41—C46	−179.84 (19)
N27—C27—C21—C22	177.60 (19)	C46—C41—C42—C43	−0.1 (3)
C26—C21—C22—C23	0.0 (3)	C47—C41—C42—C43	179.5 (2)
C27—C21—C22—C23	177.53 (18)	C41—C42—C43—F43	177.9 (2)
C21—C22—C23—F23	−179.61 (18)	C41—C42—C43—C44	−0.1 (4)
C21—C22—C23—C24	0.0 (3)	F43—C43—C44—C45	−178.0 (2)
F23—C23—C24—C25	179.58 (19)	C42—C43—C44—C45	0.2 (4)
C22—C23—C24—C25	0.0 (3)	C43—C44—C45—F45	173.0 (3)
C23—C24—C25—C26	0.0 (3)	C43—C44—C45—C46	0.1 (3)
C24—C25—C26—C21	0.0 (3)	F45—C45—C46—C41	−173.0 (3)
C22—C21—C26—C25	−0.1 (3)	C44—C45—C46—C41	−0.3 (3)
C27—C21—C26—C25	−177.37 (19)	C42—C41—C46—C45	0.3 (3)
C36—N31—C32—C33	0.9 (3)	C47—C41—C46—C45	−179.35 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O3	0.88	2.09	2.937 (2)	162
N37—H37···N27^i	0.88	2.53	3.381 (2)	162
C24—H24···N31^ii	0.95	2.59	3.517 (3)	166
C44—H44···N11^iii	0.95	2.48	3.414 (3)	167

Symmetry codes: (i) x−1/2, −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

Crystal data

C13H10FN3O·H2O	F(000) = 544
Mr = 261.26	Dx = 1.443 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1630 reflections
a = 6.4189 (3) Å	θ = 3.0–27.5°
b = 6.8520 (3) Å	µ = 0.11 mm^−1
c = 27.3451 (12) Å	T = 120 K
V = 1202.70 (9) Å^3	Block, colourless
Z = 4	0.48 × 0.38 × 0.22 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	1630 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1412 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ & ω scans	h = −7→8
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −8→8
Tmin = 0.960, Tmax = 0.976	l = −35→34
8595 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.2601P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1630 reflections	Δρmax = 0.21 e Å^−3
176 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Absolute structure: Friedel pairs merged
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.1309 (3)	0.1955 (2)	0.79927 (6)	0.0226 (4)
C12	0.0466 (3)	0.1661 (3)	0.75506 (7)	0.0208 (4)
C13	0.1535 (3)	0.1943 (3)	0.71156 (7)	0.0192 (4)
C14	0.3602 (3)	0.2524 (3)	0.71330 (7)	0.0177 (4)
C15	0.4512 (3)	0.2827 (3)	0.75919 (7)	0.0214 (4)
C16	0.3300 (3)	0.2539 (3)	0.80056 (7)	0.0237 (4)
C17	0.4957 (3)	0.2774 (3)	0.66882 (6)	0.0185 (4)
O1	0.6837 (2)	0.2441 (2)	0.67050 (5)	0.0246 (3)
N17	0.3945 (2)	0.3369 (2)	0.62815 (6)	0.0195 (4)
N27	0.5123 (2)	0.3767 (2)	0.58669 (5)	0.0196 (3)
C27	0.4069 (3)	0.4085 (3)	0.54793 (7)	0.0196 (4)
C21	0.5097 (3)	0.4644 (3)	0.50215 (7)	0.0183 (4)
C22	0.3966 (3)	0.4563 (3)	0.45859 (7)	0.0205 (4)
C23	0.4844 (3)	0.5159 (3)	0.41463 (7)	0.0225 (4)
C24	0.6858 (3)	0.5828 (3)	0.41546 (7)	0.0214 (4)
F24	0.77439 (19)	0.64424 (19)	0.37277 (4)	0.0309 (3)
C25	0.8048 (3)	0.5928 (3)	0.45748 (7)	0.0214 (4)
C26	0.7147 (3)	0.5337 (3)	0.50133 (7)	0.0198 (4)
O2	−0.0118 (2)	0.4809 (2)	0.61671 (5)	0.0221 (3)
H12	−0.0941	0.1238	0.7534	0.025*
H13	0.0861	0.1740	0.6810	0.023*
H15	0.5927	0.3220	0.7619	0.026*
H16	0.3917	0.2769	0.8316	0.028*
H17	0.2585	0.3689	0.6288	0.023*
H27	0.2595	0.3958	0.5488	0.024*
H22	0.2574	0.4093	0.4590	0.025*
H23	0.4075	0.5105	0.3850	0.027*
H25	0.9443	0.6387	0.4565	0.026*
H26	0.7926	0.5404	0.5308	0.024*
H2A	−0.0294	0.5613	0.6395	0.033*
H2B	−0.1175	0.4087	0.6160	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0230 (8)	0.0242 (9)	0.0205 (8)	0.0013 (7)	0.0018 (7)	0.0027 (7)
C12	0.0166 (9)	0.0221 (9)	0.0236 (9)	−0.0007 (8)	−0.0003 (8)	0.0029 (8)
C13	0.0184 (9)	0.0207 (9)	0.0186 (9)	0.0006 (8)	−0.0021 (7)	0.0005 (8)
C14	0.0189 (9)	0.0156 (8)	0.0187 (9)	0.0005 (8)	0.0006 (7)	0.0016 (8)
C15	0.0194 (9)	0.0214 (9)	0.0234 (9)	−0.0010 (8)	−0.0026 (8)	−0.0006 (8)
C16	0.0242 (10)	0.0271 (10)	0.0197 (9)	0.0001 (10)	−0.0028 (8)	−0.0009 (8)
C17	0.0161 (9)	0.0191 (9)	0.0203 (9)	−0.0006 (8)	0.0018 (7)	−0.0008 (7)
O1	0.0150 (6)	0.0338 (8)	0.0250 (7)	0.0008 (7)	0.0012 (5)	0.0045 (6)
N17	0.0156 (7)	0.0253 (9)	0.0176 (8)	0.0006 (7)	0.0038 (6)	0.0022 (7)
N27	0.0197 (8)	0.0215 (8)	0.0175 (7)	0.0001 (7)	0.0051 (6)	0.0002 (6)
C27	0.0164 (8)	0.0213 (9)	0.0211 (9)	−0.0011 (8)	0.0033 (8)	−0.0001 (8)
C21	0.0189 (8)	0.0159 (8)	0.0200 (9)	0.0021 (8)	0.0029 (8)	−0.0007 (7)
C22	0.0175 (9)	0.0210 (9)	0.0230 (9)	0.0005 (8)	0.0015 (8)	−0.0016 (8)
C23	0.0234 (9)	0.0242 (10)	0.0199 (9)	0.0007 (9)	−0.0007 (8)	−0.0016 (8)
C24	0.0262 (9)	0.0190 (9)	0.0188 (9)	0.0026 (8)	0.0077 (8)	0.0006 (8)
F24	0.0340 (7)	0.0364 (7)	0.0222 (6)	−0.0026 (6)	0.0090 (5)	0.0056 (5)
C25	0.0187 (9)	0.0182 (9)	0.0274 (10)	−0.0020 (8)	0.0029 (8)	−0.0016 (8)
C26	0.0199 (9)	0.0177 (9)	0.0217 (9)	−0.0002 (8)	−0.0017 (8)	−0.0021 (8)
O2	0.0178 (6)	0.0260 (7)	0.0224 (7)	−0.0012 (6)	0.0031 (5)	−0.0031 (6)

Geometric parameters (Å, º)

N11—C12	1.339 (2)	C27—C21	1.466 (2)
N11—C16	1.340 (3)	C27—H27	0.95
C12—C13	1.387 (3)	C21—C22	1.396 (2)
C12—H12	0.95	C21—C26	1.399 (3)
C13—C14	1.386 (3)	C22—C23	1.389 (3)
C13—H13	0.95	C22—H22	0.95
C14—C15	1.400 (3)	C23—C24	1.372 (3)
C14—C17	1.505 (2)	C23—H23	0.95
C15—C16	1.387 (3)	C24—F24	1.365 (2)
C15—H15	0.95	C24—C25	1.381 (3)
C16—H16	0.95	C25—C26	1.392 (3)
C17—O1	1.229 (2)	C25—H25	0.95
C17—N17	1.351 (2)	C26—H26	0.95
N17—N27	1.390 (2)	O2—H2A	0.84
N17—H17	0.90	O2—H2B	0.84
N27—C27	1.276 (2)
C12—N11—C16	116.98 (17)	N27—C27—C21	120.99 (17)
N11—C12—C13	123.62 (17)	N27—C27—H27	119.5
N11—C12—H12	118.2	C21—C27—H27	119.5
C13—C12—H12	118.2	C22—C21—C26	119.27 (17)
C14—C13—C12	118.95 (18)	C22—C21—C27	118.95 (17)
C14—C13—H13	120.5	C26—C21—C27	121.71 (17)
C12—C13—H13	120.5	C23—C22—C21	121.06 (18)
C13—C14—C15	118.23 (17)	C23—C22—H22	119.5
C13—C14—C17	123.93 (17)	C21—C22—H22	119.5
C15—C14—C17	117.79 (16)	C24—C23—C22	117.78 (18)
C16—C15—C14	118.41 (17)	C24—C23—H23	121.1
C16—C15—H15	120.8	C22—C23—H23	121.1
C14—C15—H15	120.8	F24—C24—C23	118.77 (18)
N11—C16—C15	123.79 (18)	F24—C24—C25	117.79 (17)
N11—C16—H16	118.1	C23—C24—C25	123.44 (18)
C15—C16—H16	118.1	C24—C25—C26	118.23 (18)
O1—C17—N17	123.98 (17)	C24—C25—H25	120.9
O1—C17—C14	121.07 (17)	C26—C25—H25	120.9
N17—C17—C14	114.95 (15)	C25—C26—C21	120.22 (17)
C17—N17—N27	117.96 (15)	C25—C26—H26	119.9
C17—N17—H17	121.5	C21—C26—H26	119.9
N27—N17—H17	119.8	H2A—O2—H2B	107.2
C27—N27—N17	114.97 (15)
C16—N11—C12—C13	−0.5 (3)	C17—N17—N27—C27	171.65 (17)
N11—C12—C13—C14	1.3 (3)	N17—N27—C27—C21	176.14 (16)
C12—C13—C14—C15	−0.8 (3)	N27—C27—C21—C22	166.14 (18)
C12—C13—C14—C17	176.66 (17)	N27—C27—C21—C26	−16.8 (3)
C13—C14—C15—C16	−0.3 (3)	C26—C21—C22—C23	0.0 (3)
C17—C14—C15—C16	−177.91 (18)	C27—C21—C22—C23	177.15 (18)
C12—N11—C16—C15	−0.8 (3)	C21—C22—C23—C24	0.0 (3)
C14—C15—C16—N11	1.1 (3)	C22—C23—C24—F24	−179.26 (18)
C13—C14—C17—O1	−147.6 (2)	C22—C23—C24—C25	0.3 (3)
C15—C14—C17—O1	29.9 (3)	F24—C24—C25—C26	178.91 (17)
C13—C14—C17—N17	32.1 (3)	C23—C24—C25—C26	−0.7 (3)
C15—C14—C17—N17	−150.38 (18)	C24—C25—C26—C21	0.7 (3)
O1—C17—N17—N27	−4.9 (3)	C22—C21—C26—C25	−0.3 (3)
C14—C17—N17—N27	175.40 (15)	C27—C21—C26—C25	−177.43 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O2	0.90	1.93	2.8059 (18)	165
O2—H2A···N11^i	0.84	2.02	2.833 (2)	163
O2—H2B···O1^ii	0.84	2.26	2.9354 (19)	137
O2—H2B···N27^ii	0.84	2.52	3.2427 (18)	145

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x−1, y, z.

(V) N-isonicotinoyl 2-chlorobenzaldehydehydrazone

Crystal data

C13H10ClN3O	F(000) = 536
Mr = 259.69	Dx = 1.440 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2757 reflections
a = 7.9977 (2) Å	θ = 3.5–27.5°
b = 6.7184 (2) Å	µ = 0.31 mm^−1
c = 22.5514 (6) Å	T = 120 K
β = 98.609 (3)°	Plate, colourless
V = 1198.07 (6) Å^3	0.40 × 0.14 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2757 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
ϕ & ω scans	h = −10→10
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −7→8
Tmin = 0.893, Tmax = 0.994	l = −29→29
18325 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.4843P] where P = (Fo^2 + 2Fc^2)/3
2757 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	−0.07515 (16)	0.1695 (2)	0.67399 (6)	0.0214 (3)
C12	0.01389 (19)	0.3068 (2)	0.64910 (7)	0.0208 (3)
C13	0.18814 (19)	0.3082 (2)	0.65489 (7)	0.0192 (3)
C14	0.27868 (18)	0.1597 (2)	0.68869 (6)	0.0161 (3)
C15	0.18877 (19)	0.0168 (2)	0.71512 (7)	0.0201 (3)
C16	0.01336 (19)	0.0271 (3)	0.70645 (7)	0.0227 (4)
C17	0.46874 (18)	0.1534 (2)	0.70072 (7)	0.0157 (3)
O1	0.54326 (13)	0.10882 (17)	0.75062 (5)	0.0211 (3)
N17	0.55609 (15)	0.19946 (19)	0.65557 (5)	0.0161 (3)
N27	0.47650 (16)	0.21267 (19)	0.59726 (5)	0.0165 (3)
C27	0.57369 (18)	0.2355 (2)	0.55758 (7)	0.0170 (3)
C21	0.5007 (2)	0.2480 (2)	0.49427 (7)	0.0165 (3)
C22	0.60118 (19)	0.2658 (2)	0.44858 (7)	0.0181 (3)
Cl22	0.82143 (5)	0.27586 (7)	0.466582 (18)	0.02905 (14)
C23	0.5319 (2)	0.2757 (2)	0.38862 (7)	0.0212 (3)
C24	0.3585 (2)	0.2667 (2)	0.37239 (7)	0.0225 (3)
C25	0.2548 (2)	0.2456 (2)	0.41642 (7)	0.0223 (3)
C26	0.32502 (19)	0.2373 (2)	0.47628 (7)	0.0192 (3)
H12	−0.0465	0.4094	0.6261	0.025*
H13	0.2453	0.4087	0.6361	0.023*
H15	0.2462	−0.0864	0.7388	0.024*
H16	−0.0471	−0.0721	0.7245	0.027*
H17	0.6666	0.1849	0.6631	0.019*
H27	0.6926	0.2442	0.5692	0.020*
H23	0.6033	0.2887	0.3587	0.025*
H24	0.3101	0.2749	0.3313	0.027*
H25	0.1357	0.2369	0.4053	0.027*
H26	0.2528	0.2241	0.5059	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0143 (6)	0.0298 (8)	0.0202 (7)	−0.0003 (5)	0.0023 (5)	−0.0005 (6)
C12	0.0175 (8)	0.0230 (8)	0.0218 (8)	0.0032 (6)	0.0024 (6)	0.0018 (6)
C13	0.0161 (7)	0.0206 (8)	0.0214 (8)	−0.0010 (6)	0.0047 (6)	0.0007 (6)
C14	0.0146 (7)	0.0210 (8)	0.0130 (7)	−0.0005 (6)	0.0023 (6)	−0.0027 (6)
C15	0.0167 (8)	0.0253 (8)	0.0177 (8)	0.0000 (6)	0.0004 (6)	0.0039 (6)
C16	0.0170 (8)	0.0309 (9)	0.0203 (8)	−0.0052 (6)	0.0032 (6)	0.0033 (7)
C17	0.0146 (7)	0.0154 (7)	0.0173 (8)	−0.0001 (6)	0.0030 (6)	−0.0014 (6)
O1	0.0176 (6)	0.0291 (6)	0.0157 (5)	−0.0001 (5)	−0.0007 (4)	0.0026 (5)
N17	0.0095 (6)	0.0237 (7)	0.0145 (6)	0.0000 (5)	0.0002 (5)	−0.0007 (5)
N27	0.0169 (6)	0.0196 (6)	0.0128 (6)	0.0008 (5)	0.0011 (5)	0.0000 (5)
C27	0.0153 (7)	0.0180 (8)	0.0180 (8)	−0.0004 (6)	0.0033 (6)	−0.0007 (6)
C21	0.0198 (7)	0.0138 (7)	0.0164 (8)	0.0000 (6)	0.0039 (6)	−0.0003 (6)
C22	0.0194 (7)	0.0164 (8)	0.0192 (8)	−0.0015 (6)	0.0052 (6)	0.0000 (6)
Cl22	0.0196 (2)	0.0445 (3)	0.0246 (2)	−0.00346 (17)	0.00826 (16)	0.00145 (18)
C23	0.0302 (9)	0.0169 (8)	0.0181 (8)	−0.0021 (6)	0.0088 (7)	−0.0003 (6)
C24	0.0313 (9)	0.0199 (8)	0.0155 (8)	−0.0003 (7)	0.0002 (7)	0.0004 (6)
C25	0.0212 (8)	0.0242 (8)	0.0203 (8)	0.0027 (7)	−0.0013 (6)	−0.0003 (6)
C26	0.0196 (7)	0.0203 (8)	0.0181 (8)	0.0020 (6)	0.0040 (6)	0.0004 (6)

Geometric parameters (Å, º)

N11—C12	1.339 (2)	N27—C27	1.2793 (19)
N11—C16	1.341 (2)	C27—C21	1.462 (2)
C12—C13	1.380 (2)	C27—H27	0.95
C12—H12	0.95	C21—C22	1.403 (2)
C13—C14	1.391 (2)	C21—C26	1.405 (2)
C13—H13	0.95	C22—C23	1.384 (2)
C14—C15	1.386 (2)	C22—Cl22	1.7488 (16)
C14—C17	1.504 (2)	C23—C24	1.382 (2)
C15—C16	1.389 (2)	C23—H23	0.95
C15—H15	0.95	C24—C25	1.393 (2)
C16—H16	0.95	C24—H24	0.95
C17—O1	1.2291 (18)	C25—C26	1.383 (2)
C17—N17	1.3538 (19)	C25—H25	0.95
N17—N27	1.3755 (17)	C26—H26	0.95
N17—H17	0.88
C12—N11—C16	116.74 (13)	C27—N27—N17	115.71 (12)
N11—C12—C13	123.91 (15)	N27—C27—C21	119.64 (13)
N11—C12—H12	118.0	N27—C27—H27	120.2
C13—C12—H12	118.0	C21—C27—H27	120.2
C12—C13—C14	118.85 (14)	C22—C21—C26	116.75 (14)
C12—C13—H13	120.6	C22—C21—C27	122.24 (14)
C14—C13—H13	120.6	C26—C21—C27	121.00 (13)
C15—C14—C13	118.10 (14)	C23—C22—C21	122.15 (14)
C15—C14—C17	118.57 (13)	C23—C22—Cl22	117.83 (12)
C13—C14—C17	123.24 (13)	C21—C22—Cl22	120.02 (12)
C14—C15—C16	118.89 (15)	C24—C23—C22	119.71 (14)
C14—C15—H15	120.6	C24—C23—H23	120.1
C16—C15—H15	120.6	C22—C23—H23	120.1
N11—C16—C15	123.51 (15)	C23—C24—C25	119.77 (15)
N11—C16—H16	118.2	C23—C24—H24	120.1
C15—C16—H16	118.2	C25—C24—H24	120.1
O1—C17—N17	120.67 (13)	C26—C25—C24	120.13 (15)
O1—C17—C14	120.69 (13)	C26—C25—H25	119.9
N17—C17—C14	118.64 (13)	C24—C25—H25	119.9
C17—N17—N27	121.11 (12)	C25—C26—C21	121.47 (14)
C17—N17—H17	116.5	C25—C26—H26	119.3
N27—N17—H17	120.0	C21—C26—H26	119.3
C16—N11—C12—C13	0.3 (2)	N17—N27—C27—C21	179.08 (12)
N11—C12—C13—C14	−0.3 (2)	N27—C27—C21—C22	−177.67 (14)
C12—C13—C14—C15	0.0 (2)	N27—C27—C21—C26	0.6 (2)
C12—C13—C14—C17	−176.53 (14)	C26—C21—C22—C23	1.0 (2)
C13—C14—C15—C16	0.4 (2)	C27—C21—C22—C23	179.38 (14)
C17—C14—C15—C16	177.09 (14)	C26—C21—C22—Cl22	−178.92 (11)
C12—N11—C16—C15	0.1 (2)	C27—C21—C22—Cl22	−0.6 (2)
C14—C15—C16—N11	−0.5 (2)	C21—C22—C23—C24	−0.4 (2)
C15—C14—C17—O1	−38.0 (2)	Cl22—C22—C23—C24	179.49 (12)
C13—C14—C17—O1	138.45 (16)	C22—C23—C24—C25	−0.7 (2)
C15—C14—C17—N17	142.48 (15)	C23—C24—C25—C26	1.2 (2)
C13—C14—C17—N17	−41.0 (2)	C24—C25—C26—C21	−0.6 (2)
O1—C17—N17—N27	167.57 (13)	C22—C21—C26—C25	−0.5 (2)
C14—C17—N17—N27	−12.9 (2)	C27—C21—C26—C25	−178.89 (14)
C17—N17—N27—C27	−172.66 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N11^i	0.88	2.05	2.923 (2)	175
C23—H23···O1^ii	0.95	2.51	3.222 (2)	132
C16—H16···Cg3^iii	0.95	2.95	3.723 (2)	154

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) −x, y+3/2, −z+3/2.

(VI) N-isonicotinoyl 3-chlorobenzaldehydehydrazone

Crystal data

C13H10ClN3O	F(000) = 536
Mr = 259.69	Dx = 1.467 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2691 reflections
a = 7.4524 (3) Å	θ = 2.3–27.5°
b = 11.2367 (4) Å	µ = 0.32 mm^−1
c = 14.3949 (3) Å	T = 120 K
β = 102.701 (2)°	Block, colourless
V = 1175.94 (7) Å^3	0.34 × 0.28 × 0.18 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2691 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
ϕ & ω scans	h = −8→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.886, Tmax = 0.946	l = −15→18
15675 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0972P)^2 + 0.0157P] where P = (Fo^2 + 2Fc^2)/3
2691 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.33989 (19)	0.02209 (12)	0.21775 (9)	0.0201 (3)
C12	0.2546 (2)	0.12766 (15)	0.21030 (11)	0.0205 (4)
C13	0.2716 (2)	0.20830 (14)	0.28515 (10)	0.0189 (3)
C14	0.3828 (2)	0.17859 (13)	0.37300 (10)	0.0173 (3)
C15	0.4760 (2)	0.07098 (15)	0.38044 (10)	0.0193 (4)
C16	0.4504 (2)	−0.00387 (15)	0.30272 (11)	0.0212 (4)
C17	0.4036 (2)	0.25233 (14)	0.46237 (10)	0.0192 (4)
O1	0.49112 (18)	0.21469 (11)	0.53817 (7)	0.0310 (3)
N17	0.31632 (18)	0.36002 (12)	0.45326 (8)	0.0185 (3)
N27	0.32877 (19)	0.42603 (12)	0.53490 (9)	0.0187 (3)
C27	0.2404 (2)	0.52468 (14)	0.52636 (10)	0.0183 (3)
C21	0.2506 (2)	0.60117 (14)	0.61006 (10)	0.0181 (3)
C22	0.3610 (2)	0.57045 (14)	0.69811 (10)	0.0194 (4)
C23	0.3677 (2)	0.64497 (16)	0.77489 (11)	0.0226 (4)
Cl23	0.50652 (7)	0.60557 (4)	0.88451 (3)	0.0389 (2)
C24	0.2685 (2)	0.75100 (15)	0.76697 (12)	0.0251 (4)
C25	0.1614 (2)	0.78112 (15)	0.67912 (12)	0.0257 (4)
C26	0.1511 (2)	0.70700 (15)	0.60082 (11)	0.0226 (4)
H12	0.1783	0.1487	0.1506	0.025*
H13	0.2084	0.2823	0.2764	0.023*
H15	0.5569	0.0490	0.4386	0.023*
H16	0.5140	−0.0777	0.3094	0.025*
H17	0.2549	0.3860	0.3976	0.022*
H27	0.1686	0.5482	0.4662	0.022*
H22	0.4308	0.4990	0.7051	0.023*
H24	0.2745	0.8013	0.8206	0.030*
H25	0.0938	0.8535	0.6721	0.031*
H26	0.0761	0.7286	0.5409	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0232 (7)	0.0182 (7)	0.0181 (6)	−0.0010 (6)	0.0028 (5)	−0.0022 (5)
C12	0.0263 (9)	0.0192 (8)	0.0146 (7)	−0.0017 (7)	0.0012 (6)	0.0001 (6)
C13	0.0228 (8)	0.0148 (8)	0.0179 (7)	0.0016 (6)	0.0023 (6)	0.0011 (6)
C14	0.0201 (8)	0.0157 (8)	0.0160 (7)	−0.0037 (6)	0.0037 (6)	−0.0006 (6)
C15	0.0215 (8)	0.0193 (8)	0.0160 (7)	0.0002 (6)	0.0014 (6)	0.0006 (6)
C16	0.0221 (8)	0.0186 (8)	0.0220 (8)	0.0025 (6)	0.0032 (6)	0.0005 (6)
C17	0.0239 (9)	0.0169 (8)	0.0156 (7)	−0.0016 (6)	0.0021 (6)	−0.0003 (6)
O1	0.0481 (8)	0.0226 (7)	0.0172 (6)	0.0079 (6)	−0.0038 (5)	−0.0019 (5)
N17	0.0259 (7)	0.0164 (7)	0.0121 (6)	0.0002 (6)	0.0019 (5)	−0.0021 (5)
N27	0.0252 (7)	0.0178 (7)	0.0131 (6)	−0.0024 (6)	0.0043 (5)	−0.0022 (5)
C27	0.0214 (8)	0.0180 (8)	0.0160 (7)	−0.0008 (6)	0.0053 (6)	0.0003 (6)
C21	0.0210 (8)	0.0170 (8)	0.0175 (8)	−0.0031 (6)	0.0068 (6)	0.0007 (6)
C22	0.0231 (8)	0.0156 (8)	0.0198 (8)	−0.0016 (6)	0.0057 (6)	−0.0018 (6)
C23	0.0279 (9)	0.0217 (9)	0.0185 (8)	−0.0061 (7)	0.0056 (6)	−0.0029 (6)
Cl23	0.0563 (4)	0.0348 (3)	0.0196 (3)	0.0020 (2)	−0.0046 (2)	−0.00640 (17)
C24	0.0332 (10)	0.0193 (9)	0.0259 (8)	−0.0046 (7)	0.0130 (7)	−0.0076 (6)
C25	0.0316 (10)	0.0165 (8)	0.0321 (9)	0.0015 (7)	0.0141 (7)	−0.0015 (7)
C26	0.0252 (9)	0.0202 (9)	0.0232 (8)	−0.0005 (7)	0.0067 (6)	0.0014 (6)

Geometric parameters (Å, º)

N11—C12	1.339 (2)	N27—C27	1.281 (2)
N11—C16	1.348 (2)	C27—C21	1.468 (2)
C12—C13	1.392 (2)	C27—H27	0.95
C12—H12	0.95	C21—C26	1.392 (2)
C13—C14	1.392 (2)	C21—C22	1.394 (2)
C13—H13	0.95	C22—C23	1.379 (2)
C14—C15	1.387 (2)	C22—H22	0.95
C14—C17	1.509 (2)	C23—C24	1.394 (3)
C15—C16	1.379 (2)	C23—Cl23	1.7429 (17)
C15—H15	0.95	C24—C25	1.381 (2)
C16—H16	0.95	C24—H24	0.95
C17—O1	1.2172 (18)	C25—C26	1.390 (2)
C17—N17	1.366 (2)	C25—H25	0.95
N17—N27	1.3755 (17)	C26—H26	0.95
N17—H17	0.88
C12—N11—C16	116.68 (13)	C27—N27—N17	116.61 (13)
N11—C12—C13	123.64 (14)	N27—C27—C21	119.67 (14)
N11—C12—H12	118.2	N27—C27—H27	120.2
C13—C12—H12	118.2	C21—C27—H27	120.2
C14—C13—C12	118.81 (15)	C26—C21—C22	119.59 (14)
C14—C13—H13	120.6	C26—C21—C27	119.42 (14)
C12—C13—H13	120.6	C22—C21—C27	120.98 (14)
C15—C14—C13	117.86 (14)	C23—C22—C21	119.25 (15)
C15—C14—C17	117.19 (13)	C23—C22—H22	120.4
C13—C14—C17	124.90 (14)	C21—C22—H22	120.4
C16—C15—C14	119.43 (14)	C22—C23—C24	121.90 (15)
C16—C15—H15	120.3	C22—C23—Cl23	118.77 (14)
C14—C15—H15	120.3	C24—C23—Cl23	119.33 (12)
N11—C16—C15	123.54 (15)	C25—C24—C23	118.30 (15)
N11—C16—H16	118.2	C25—C24—H24	120.9
C15—C16—H16	118.2	C23—C24—H24	120.9
O1—C17—N17	122.93 (14)	C24—C25—C26	120.89 (16)
O1—C17—C14	120.52 (14)	C24—C25—H25	119.6
N17—C17—C14	116.53 (12)	C26—C25—H25	119.6
C17—N17—N27	117.02 (12)	C25—C26—C21	120.07 (15)
C17—N17—H17	121.5	C25—C26—H26	120.0
N27—N17—H17	121.5	C21—C26—H26	120.0
C16—N11—C12—C13	−1.4 (2)	C17—N17—N27—C27	−177.27 (14)
N11—C12—C13—C14	−0.1 (2)	N17—N27—C27—C21	−178.64 (13)
C12—C13—C14—C15	2.0 (2)	N27—C27—C21—C26	−178.61 (15)
C12—C13—C14—C17	−175.23 (14)	N27—C27—C21—C22	2.6 (2)
C13—C14—C15—C16	−2.4 (2)	C26—C21—C22—C23	0.8 (2)
C17—C14—C15—C16	175.05 (14)	C27—C21—C22—C23	179.62 (14)
C12—N11—C16—C15	1.0 (2)	C21—C22—C23—C24	−0.6 (2)
C14—C15—C16—N11	0.9 (2)	C21—C22—C23—Cl23	−179.93 (12)
C15—C14—C17—O1	−3.8 (2)	C22—C23—C24—C25	−0.2 (3)
C13—C14—C17—O1	173.48 (15)	Cl23—C23—C24—C25	179.17 (13)
C15—C14—C17—N17	177.74 (14)	C23—C24—C25—C26	0.7 (3)
C13—C14—C17—N17	−5.0 (2)	C24—C25—C26—C21	−0.5 (3)
O1—C17—N17—N27	−0.8 (2)	C22—C21—C26—C25	−0.3 (2)
C14—C17—N17—N27	177.67 (13)	C27—C21—C26—C25	−179.11 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N11^i	0.88	2.25	3.0776 (18)	156
C12—H12···O1^ii	0.95	2.43	3.316 (2)	154

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

(VIII) N-isonicotinoyl 2-bromobenzaldehydehydrazone

Crystal data

C13H10BrN3O	F(000) = 608
Mr = 304.15	Dx = 1.688 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2746 reflections
a = 8.0268 (2) Å	θ = 3.2–27.7°
b = 6.7134 (3) Å	µ = 3.43 mm^−1
c = 22.5024 (10) Å	T = 120 K
β = 99.297 (3)°	Lath, colourless
V = 1196.66 (8) Å^3	0.12 × 0.03 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2746 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2182 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 9.091 pixels mm^-1	θmax = 27.7°, θmin = 3.2°
ϕ & ω scans	h = −9→10
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −8→8
Tmin = 0.654, Tmax = 0.935	l = −29→29
11911 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0225P)^2 + 1.7209P] where P = (Fo^2 + 2Fc^2)/3
2746 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.58 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	−0.0743 (3)	0.1663 (4)	0.67403 (12)	0.0203 (6)
C12	0.0136 (4)	0.3048 (5)	0.64913 (14)	0.0200 (6)
C13	0.1868 (4)	0.3046 (5)	0.65474 (14)	0.0179 (6)
C14	0.2776 (3)	0.1554 (4)	0.68826 (13)	0.0151 (6)
C15	0.1892 (4)	0.0128 (5)	0.71467 (14)	0.0184 (6)
C16	0.0146 (4)	0.0233 (5)	0.70585 (14)	0.0218 (7)
C17	0.4682 (3)	0.1487 (4)	0.70088 (13)	0.0150 (6)
O1	0.5423 (2)	0.1039 (3)	0.75071 (9)	0.0197 (5)
N17	0.5537 (3)	0.1969 (4)	0.65575 (11)	0.0150 (5)
N27	0.4743 (3)	0.2120 (4)	0.59707 (11)	0.0147 (5)
C27	0.5722 (4)	0.2340 (4)	0.55812 (13)	0.0156 (6)
C21	0.5022 (4)	0.2478 (4)	0.49409 (13)	0.0144 (6)
C22	0.6039 (4)	0.2648 (4)	0.44941 (14)	0.0169 (6)
Br22	0.84348 (4)	0.27171 (5)	0.470142 (14)	0.02685 (13)
C23	0.5372 (4)	0.2772 (4)	0.38870 (14)	0.0188 (6)
C24	0.3636 (4)	0.2694 (4)	0.37134 (14)	0.0210 (7)
C25	0.2599 (4)	0.2477 (4)	0.41460 (14)	0.0198 (7)
C26	0.3274 (4)	0.2390 (4)	0.47474 (14)	0.0183 (6)
H12	−0.0472	0.4085	0.6264	0.024*
H13	0.2434	0.4051	0.6360	0.022*
H15	0.2471	−0.0906	0.7384	0.022*
H16	−0.0451	−0.0771	0.7235	0.026*
H17	0.6731	0.1758	0.6597	0.018*
H27	0.6908	0.2415	0.5708	0.019*
H23	0.6095	0.2908	0.3594	0.023*
H24	0.3158	0.2788	0.3300	0.025*
H25	0.1411	0.2388	0.4026	0.024*
H26	0.2541	0.2268	0.5037	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0126 (12)	0.0304 (16)	0.0181 (14)	−0.0005 (10)	0.0025 (10)	−0.0026 (12)
C12	0.0218 (15)	0.0204 (17)	0.0175 (16)	0.0015 (12)	0.0019 (12)	0.0008 (13)
C13	0.0179 (14)	0.0189 (16)	0.0176 (16)	−0.0013 (11)	0.0049 (12)	−0.0009 (12)
C14	0.0154 (14)	0.0188 (16)	0.0119 (15)	0.0009 (11)	0.0042 (11)	−0.0031 (12)
C15	0.0176 (14)	0.0239 (17)	0.0140 (16)	−0.0014 (12)	0.0034 (11)	0.0031 (13)
C16	0.0207 (15)	0.0273 (18)	0.0171 (17)	−0.0055 (12)	0.0027 (12)	0.0049 (13)
C17	0.0164 (14)	0.0168 (16)	0.0115 (15)	−0.0017 (11)	0.0018 (11)	−0.0021 (12)
O1	0.0188 (11)	0.0278 (13)	0.0116 (11)	−0.0014 (9)	−0.0003 (8)	0.0033 (9)
N17	0.0117 (11)	0.0225 (14)	0.0107 (13)	0.0005 (9)	0.0015 (9)	−0.0012 (10)
N27	0.0141 (11)	0.0190 (13)	0.0107 (12)	−0.0003 (9)	0.0017 (9)	−0.0015 (10)
C27	0.0163 (14)	0.0154 (15)	0.0145 (15)	0.0005 (11)	0.0004 (11)	−0.0022 (12)
C21	0.0179 (14)	0.0142 (15)	0.0112 (14)	0.0012 (10)	0.0028 (11)	−0.0011 (11)
C22	0.0173 (14)	0.0153 (15)	0.0185 (16)	−0.0017 (11)	0.0042 (11)	0.0000 (12)
Br22	0.01710 (18)	0.0442 (2)	0.02051 (19)	−0.00275 (13)	0.00674 (12)	0.00206 (15)
C23	0.0277 (16)	0.0138 (15)	0.0165 (16)	−0.0024 (12)	0.0087 (12)	−0.0008 (12)
C24	0.0288 (17)	0.0207 (17)	0.0131 (16)	0.0003 (13)	0.0021 (12)	0.0013 (13)
C25	0.0192 (15)	0.0207 (17)	0.0183 (16)	0.0039 (12)	−0.0005 (12)	−0.0002 (13)
C26	0.0180 (15)	0.0194 (16)	0.0181 (16)	0.0004 (11)	0.0045 (12)	−0.0016 (13)

Geometric parameters (Å, º)

N11—C16	1.334 (4)	N27—C27	1.276 (4)
N11—C12	1.343 (4)	C27—C21	1.462 (4)
C12—C13	1.375 (4)	C27—H27	0.95
C12—H12	0.95	C21—C22	1.398 (4)
C13—C14	1.388 (4)	C21—C26	1.402 (4)
C13—H13	0.95	C22—C23	1.387 (4)
C14—C15	1.382 (4)	C22—Br22	1.905 (3)
C14—C17	1.511 (4)	C23—C24	1.386 (4)
C15—C16	1.385 (4)	C23—H23	0.95
C15—H15	0.95	C24—C25	1.387 (4)
C16—H16	0.95	C24—H24	0.95
C17—O1	1.219 (3)	C25—C26	1.375 (4)
C17—N17	1.353 (4)	C25—H25	0.95
N17—N27	1.374 (3)	C26—H26	0.95
N17—H17	0.9588
C16—N11—C12	116.8 (3)	C27—N27—N17	115.3 (2)
N11—C12—C13	123.5 (3)	N27—C27—C21	120.2 (3)
N11—C12—H12	118.2	N27—C27—H27	119.9
C13—C12—H12	118.2	C21—C27—H27	119.9
C12—C13—C14	119.0 (3)	C22—C21—C26	116.8 (3)
C12—C13—H13	120.5	C22—C21—C27	122.5 (3)
C14—C13—H13	120.5	C26—C21—C27	120.6 (3)
C15—C14—C13	118.2 (3)	C23—C22—C21	122.4 (3)
C15—C14—C17	118.2 (3)	C23—C22—Br22	117.0 (2)
C13—C14—C17	123.4 (3)	C21—C22—Br22	120.6 (2)
C14—C15—C16	118.8 (3)	C24—C23—C22	119.1 (3)
C14—C15—H15	120.6	C24—C23—H23	120.5
C16—C15—H15	120.6	C22—C23—H23	120.5
N11—C16—C15	123.7 (3)	C23—C24—C25	119.7 (3)
N11—C16—H16	118.1	C23—C24—H24	120.1
C15—C16—H16	118.1	C25—C24—H24	120.1
O1—C17—N17	121.2 (2)	C26—C25—C24	120.6 (3)
O1—C17—C14	120.6 (3)	C26—C25—H25	119.7
N17—C17—C14	118.2 (3)	C24—C25—H25	119.7
C17—N17—N27	121.8 (2)	C25—C26—C21	121.3 (3)
C17—N17—H17	121.0	C25—C26—H26	119.4
N27—N17—H17	113.7	C21—C26—H26	119.4
C16—N11—C12—C13	0.3 (5)	N17—N27—C27—C21	178.8 (2)
N11—C12—C13—C14	−0.7 (5)	N27—C27—C21—C22	−177.6 (3)
C12—C13—C14—C15	0.0 (4)	N27—C27—C21—C26	0.6 (4)
C12—C13—C14—C17	−175.7 (3)	C26—C21—C22—C23	1.5 (4)
C13—C14—C15—C16	0.9 (4)	C27—C21—C22—C23	179.8 (3)
C17—C14—C15—C16	176.8 (3)	C26—C21—C22—Br22	−178.5 (2)
C12—N11—C16—C15	0.7 (5)	C27—C21—C22—Br22	−0.2 (4)
C14—C15—C16—N11	−1.3 (5)	C21—C22—C23—C24	−1.1 (4)
C15—C14—C17—O1	−37.8 (4)	Br22—C22—C23—C24	178.9 (2)
C13—C14—C17—O1	137.9 (3)	C22—C23—C24—C25	−0.5 (4)
C15—C14—C17—N17	143.3 (3)	C23—C24—C25—C26	1.7 (4)
C13—C14—C17—N17	−41.0 (4)	C24—C25—C26—C21	−1.2 (4)
O1—C17—N17—N27	167.9 (3)	C22—C21—C26—C25	−0.3 (4)
C14—C17—N17—N27	−13.2 (4)	C27—C21—C26—C25	−178.7 (3)
C17—N17—N27—C27	−171.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N11^i	0.96	2.00	2.955 (3)	172
C23—H23···O1^ii	0.95	2.52	3.213 (4)	130
C16—H16···Cg3^iii	0.95	2.87	3.743 (3)	154

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+3/2.

(IX) N-isonicotinoyl 3-bromobenzaldehydehydrazone

Crystal data

C13H10BrN3O	F(000) = 608
Mr = 304.15	Dx = 1.698 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2733 reflections
a = 7.4578 (2) Å	θ = 2.9–27.5°
b = 11.3264 (3) Å	µ = 3.45 mm^−1
c = 14.3558 (3) Å	T = 120 K
β = 101.119 (2)°	Plate, colourless
V = 1189.87 (5) Å^3	0.40 × 0.20 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2733 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2231 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.340, Tmax = 0.934	l = −18→18
14830 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 0.5661P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
2733 reflections	Δρmax = 0.41 e Å^−3
164 parameters	Δρmin = −0.55 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.3372 (2)	0.02360 (14)	0.21574 (11)	0.0184 (3)
C12	0.2566 (3)	0.12994 (17)	0.20990 (13)	0.0182 (4)
C13	0.2756 (3)	0.20922 (16)	0.28486 (13)	0.0165 (4)
C14	0.3841 (2)	0.17842 (16)	0.37143 (13)	0.0143 (4)
C15	0.4734 (3)	0.07005 (17)	0.37751 (13)	0.0169 (4)
C16	0.4457 (3)	−0.00363 (17)	0.29919 (13)	0.0183 (4)
C17	0.4060 (3)	0.25088 (16)	0.46118 (13)	0.0167 (4)
O1	0.4929 (2)	0.21345 (13)	0.53588 (9)	0.0267 (3)
N17	0.3190 (2)	0.35760 (14)	0.45373 (10)	0.0160 (3)
N27	0.3313 (2)	0.42289 (14)	0.53563 (11)	0.0163 (3)
C27	0.2438 (3)	0.52064 (17)	0.52817 (13)	0.0164 (4)
C21	0.2519 (3)	0.59632 (15)	0.61166 (13)	0.0152 (4)
C22	0.3607 (3)	0.56599 (17)	0.69924 (13)	0.0160 (4)
C23	0.3653 (3)	0.64066 (17)	0.77589 (13)	0.0175 (4)
Br23	0.51223 (3)	0.597016 (19)	0.894103 (14)	0.03140 (11)
C24	0.2666 (3)	0.74551 (17)	0.76882 (14)	0.0212 (4)
C25	0.1616 (3)	0.77495 (18)	0.68193 (14)	0.0222 (4)
C26	0.1521 (3)	0.70134 (17)	0.60387 (14)	0.0195 (4)
H12	0.1823	0.1522	0.1511	0.022*
H13	0.2154	0.2835	0.2771	0.020*
H15	0.5523	0.0470	0.4347	0.020*
H16	0.5068	−0.0776	0.3046	0.022*
H17	0.2679	0.3898	0.3993	0.019*
H27	0.1737	0.5441	0.4686	0.020*
H22	0.4302	0.4952	0.7059	0.019*
H24	0.2713	0.7955	0.8224	0.025*
H25	0.0947	0.8468	0.6754	0.027*
H26	0.0773	0.7225	0.5449	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0217 (8)	0.0178 (8)	0.0153 (8)	−0.0007 (7)	0.0023 (7)	−0.0033 (6)
C12	0.0218 (10)	0.0186 (9)	0.0130 (9)	−0.0001 (8)	0.0009 (8)	0.0008 (7)
C13	0.0204 (10)	0.0131 (9)	0.0161 (9)	0.0010 (7)	0.0036 (8)	−0.0005 (7)
C14	0.0151 (9)	0.0142 (9)	0.0142 (8)	−0.0023 (7)	0.0045 (7)	−0.0002 (7)
C15	0.0177 (9)	0.0178 (9)	0.0143 (9)	−0.0005 (7)	0.0006 (7)	0.0002 (7)
C16	0.0197 (10)	0.0166 (9)	0.0181 (9)	0.0015 (8)	0.0021 (8)	−0.0010 (7)
C17	0.0208 (10)	0.0148 (9)	0.0139 (8)	−0.0030 (7)	0.0023 (7)	−0.0008 (7)
O1	0.0411 (9)	0.0208 (7)	0.0146 (7)	0.0068 (7)	−0.0038 (6)	−0.0013 (6)
N17	0.0233 (8)	0.0146 (8)	0.0089 (7)	−0.0005 (7)	0.0000 (6)	−0.0015 (6)
N27	0.0213 (8)	0.0159 (8)	0.0119 (7)	−0.0025 (6)	0.0035 (6)	−0.0026 (6)
C27	0.0202 (9)	0.0169 (9)	0.0120 (8)	−0.0018 (8)	0.0029 (7)	0.0011 (7)
C21	0.0176 (9)	0.0144 (9)	0.0145 (9)	−0.0022 (7)	0.0054 (7)	0.0001 (7)
C22	0.0187 (9)	0.0142 (9)	0.0153 (9)	−0.0005 (7)	0.0039 (7)	0.0000 (7)
C23	0.0222 (10)	0.0174 (9)	0.0133 (9)	−0.0033 (8)	0.0042 (7)	0.0002 (7)
Br23	0.04584 (17)	0.02825 (15)	0.01556 (13)	0.00163 (10)	−0.00544 (10)	−0.00469 (8)
C24	0.0276 (11)	0.0170 (9)	0.0214 (9)	−0.0033 (8)	0.0113 (8)	−0.0059 (8)
C25	0.0260 (10)	0.0149 (9)	0.0280 (10)	0.0031 (8)	0.0109 (9)	0.0001 (8)
C26	0.0226 (10)	0.0184 (9)	0.0177 (9)	0.0006 (8)	0.0044 (8)	0.0030 (7)

Geometric parameters (Å, º)

N11—C12	1.341 (3)	N27—C27	1.279 (3)
N11—C16	1.346 (2)	C27—C21	1.465 (2)
C12—C13	1.388 (3)	C27—H27	0.95
C12—H12	0.95	C21—C26	1.396 (3)
C13—C14	1.390 (2)	C21—C22	1.401 (3)
C13—H13	0.95	C22—C23	1.383 (3)
C14—C15	1.391 (3)	C22—H22	0.95
C14—C17	1.510 (2)	C23—C24	1.390 (3)
C15—C16	1.383 (3)	C23—Br23	1.8996 (19)
C15—H15	0.95	C24—C25	1.380 (3)
C16—H16	0.95	C24—H24	0.95
C17—O1	1.217 (2)	C25—C26	1.387 (3)
C17—N17	1.366 (2)	C25—H25	0.95
N17—N27	1.377 (2)	C26—H26	0.95
N17—H17	0.8799
C12—N11—C16	116.52 (16)	C27—N27—N17	116.40 (16)
N11—C12—C13	123.72 (17)	N27—C27—C21	119.87 (17)
N11—C12—H12	118.1	N27—C27—H27	120.1
C13—C12—H12	118.1	C21—C27—H27	120.1
C12—C13—C14	119.06 (17)	C26—C21—C22	119.22 (17)
C12—C13—H13	120.5	C26—C21—C27	119.71 (17)
C14—C13—H13	120.5	C22—C21—C27	121.06 (17)
C13—C14—C15	117.80 (17)	C23—C22—C21	119.03 (18)
C13—C14—C17	125.12 (16)	C23—C22—H22	120.5
C15—C14—C17	117.02 (16)	C21—C22—H22	120.5
C16—C15—C14	119.12 (17)	C22—C23—C24	122.19 (18)
C16—C15—H15	120.4	C22—C23—Br23	118.24 (15)
C14—C15—H15	120.4	C24—C23—Br23	119.57 (14)
N11—C16—C15	123.72 (18)	C25—C24—C23	118.19 (18)
N11—C16—H16	118.1	C25—C24—H24	120.9
C15—C16—H16	118.1	C23—C24—H24	120.9
O1—C17—N17	122.77 (17)	C24—C25—C26	121.12 (18)
O1—C17—C14	120.94 (17)	C24—C25—H25	119.4
N17—C17—C14	116.26 (15)	C26—C25—H25	119.4
C17—N17—N27	117.12 (15)	C25—C26—C21	120.24 (18)
C17—N17—H17	123.6	C25—C26—H26	119.9
N27—N17—H17	118.8	C21—C26—H26	119.9
C16—N11—C12—C13	−1.9 (3)	C17—N17—N27—C27	−177.62 (17)
N11—C12—C13—C14	0.1 (3)	N17—N27—C27—C21	−179.09 (16)
C12—C13—C14—C15	2.0 (3)	N27—C27—C21—C26	−178.18 (18)
C12—C13—C14—C17	−174.98 (18)	N27—C27—C21—C22	2.8 (3)
C13—C14—C15—C16	−2.3 (3)	C26—C21—C22—C23	0.4 (3)
C17—C14—C15—C16	174.90 (17)	C27—C21—C22—C23	179.44 (17)
C12—N11—C16—C15	1.5 (3)	C21—C22—C23—C24	−0.5 (3)
C14—C15—C16—N11	0.6 (3)	C21—C22—C23—Br23	179.51 (14)
C13—C14—C17—O1	174.48 (19)	C22—C23—C24—C25	−0.2 (3)
C15—C14—C17—O1	−2.5 (3)	Br23—C23—C24—C25	179.79 (15)
C13—C14—C17—N17	−3.6 (3)	C23—C24—C25—C26	1.0 (3)
C15—C14—C17—N17	179.34 (17)	C24—C25—C26—C21	−1.1 (3)
O1—C17—N17—N27	−0.6 (3)	C22—C21—C26—C25	0.4 (3)
C14—C17—N17—N27	177.46 (15)	C27—C21—C26—C25	−178.65 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N11^i	0.88	2.27	3.117 (2)	163
C12—H12···O1^ii	0.95	2.48	3.371 (2)	156

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

(X) N-isonicotinoyl 4-bromobenzaldehydehydrazone

Crystal data

C13H10BrN3O·H2O	F(000) = 1296
Mr = 322.17	Dx = 1.658 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5916 reflections
a = 14.2570 (3) Å	θ = 1.6–27.5°
b = 14.6299 (4) Å	µ = 3.19 mm^−1
c = 14.1669 (4) Å	T = 120 K
β = 119.152 (2)°	Block, colourless
V = 2580.61 (12) Å^3	0.38 × 0.24 × 0.24 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	5916 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	5220 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ϕ & ω scans	h = −18→17
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −18→18
Tmin = 0.341, Tmax = 0.465	l = −16→18
28990 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.23	w = 1/[σ^2(Fo^2) + (0.017P)^2 + 24.843P] where P = (Fo^2 + 2Fc^2)/3
5916 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 2.26 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.5800 (4)	0.0327 (4)	0.7369 (4)	0.0217 (11)
C12	0.5383 (5)	0.1105 (4)	0.6845 (5)	0.0217 (13)
C13	0.5930 (5)	0.1913 (4)	0.6997 (5)	0.0205 (12)
C14	0.7025 (4)	0.1925 (4)	0.7756 (5)	0.0153 (11)
C15	0.7502 (4)	0.1119 (4)	0.8281 (5)	0.0174 (11)
C16	0.6865 (5)	0.0347 (4)	0.8089 (5)	0.0231 (13)
C17	0.7729 (5)	0.2753 (4)	0.8043 (5)	0.0171 (12)
O1	0.8715 (3)	0.2673 (3)	0.8431 (4)	0.0218 (9)
N17	0.7221 (4)	0.3567 (3)	0.7862 (4)	0.0193 (11)
N27	0.7829 (4)	0.4360 (3)	0.8169 (4)	0.0197 (11)
C27	0.7274 (5)	0.5099 (4)	0.7989 (5)	0.0218 (13)
C21	0.7799 (5)	0.6002 (4)	0.8265 (5)	0.0188 (12)
C22	0.7158 (5)	0.6780 (4)	0.8020 (5)	0.0208 (13)
C23	0.7600 (5)	0.7643 (4)	0.8269 (5)	0.0211 (13)
C24	0.8712 (5)	0.7725 (4)	0.8780 (5)	0.0196 (12)
Br24	0.93391 (5)	0.89108 (4)	0.91670 (6)	0.02576 (17)
C25	0.9369 (5)	0.6969 (4)	0.9046 (5)	0.0201 (12)
C26	0.8930 (5)	0.6114 (4)	0.8797 (6)	0.0233 (13)
O2	0.5001 (4)	0.4045 (3)	0.6585 (4)	0.0286 (11)
N31	0.1127 (5)	0.0114 (4)	0.3484 (5)	0.0245 (12)
C32	0.0596 (5)	0.0851 (4)	0.3548 (5)	0.0218 (13)
C33	0.1056 (5)	0.1708 (4)	0.3845 (5)	0.0190 (12)
C34	0.2117 (5)	0.1819 (4)	0.4092 (5)	0.0165 (11)
C35	0.2665 (5)	0.1062 (5)	0.4041 (6)	0.0240 (13)
C36	0.2147 (6)	0.0241 (5)	0.3723 (5)	0.0245 (14)
C37	0.2712 (5)	0.2711 (4)	0.4455 (5)	0.0193 (12)
O3	0.3693 (3)	0.2717 (3)	0.5027 (4)	0.0266 (10)
N37	0.2100 (4)	0.3471 (4)	0.4120 (4)	0.0198 (11)
N47	0.2627 (4)	0.4296 (4)	0.4440 (4)	0.0207 (11)
C47	0.2064 (5)	0.5023 (4)	0.4067 (5)	0.0208 (13)
C41	0.2604 (5)	0.5919 (4)	0.4393 (5)	0.0213 (13)
C42	0.1989 (5)	0.6725 (4)	0.4157 (5)	0.0215 (13)
C43	0.2491 (5)	0.7565 (5)	0.4539 (5)	0.0217 (13)
C44	0.3603 (5)	0.7598 (4)	0.5122 (5)	0.0209 (12)
Br44	0.43156 (5)	0.87230 (4)	0.56999 (6)	0.02707 (17)
C45	0.4226 (5)	0.6818 (5)	0.5320 (5)	0.0224 (13)
C46	0.3720 (5)	0.5987 (4)	0.4955 (5)	0.0233 (13)
O4	−0.0157 (4)	0.3575 (4)	0.2779 (4)	0.0356 (13)
H12	0.4643	0.1102	0.6320	0.026*
H13	0.5577	0.2446	0.6600	0.025*
H15	0.8253	0.1094	0.8766	0.021*
H16	0.7194	−0.0194	0.8482	0.028*
H17	0.6517	0.3593	0.7555	0.023*
H27	0.6515	0.5061	0.7673	0.026*
H22	0.6400	0.6714	0.7675	0.025*
H23	0.7155	0.8169	0.8095	0.025*
H25	1.0127	0.7042	0.9401	0.024*
H26	0.9383	0.5593	0.8982	0.028*
H2A	0.4385	0.3898	0.5856	0.043*
H2B	0.4670	0.4321	0.6999	0.043*
H32	−0.0131	0.0778	0.3381	0.026*
H33	0.0653	0.2212	0.3879	0.023*
H35	0.3399	0.1110	0.4227	0.029*
H36	0.2533	−0.0266	0.3667	0.029*
H37	0.1398	0.3440	0.3716	0.024*
H47	0.1313	0.4987	0.3589	0.025*
H42	0.1229	0.6695	0.3736	0.026*
H43	0.2079	0.8108	0.4402	0.026*
H45	0.4988	0.6856	0.5699	0.027*
H46	0.4141	0.5450	0.5090	0.028*
H4A	−0.0291	0.4180	0.2408	0.053*
H4B	−0.0785	0.3472	0.2898	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.021 (3)	0.017 (2)	0.025 (3)	−0.004 (2)	0.010 (2)	−0.003 (2)
C12	0.016 (3)	0.021 (3)	0.021 (3)	−0.001 (2)	0.004 (2)	0.000 (2)
C13	0.020 (3)	0.019 (3)	0.019 (3)	0.001 (2)	0.007 (2)	0.002 (2)
C14	0.013 (3)	0.017 (3)	0.016 (3)	−0.001 (2)	0.007 (2)	−0.003 (2)
C15	0.011 (2)	0.020 (3)	0.019 (3)	0.000 (2)	0.005 (2)	0.000 (2)
C16	0.025 (3)	0.016 (3)	0.026 (3)	−0.001 (2)	0.009 (3)	0.001 (2)
C17	0.016 (3)	0.017 (3)	0.018 (3)	0.001 (2)	0.008 (2)	0.000 (2)
O1	0.0115 (19)	0.020 (2)	0.031 (2)	−0.0019 (16)	0.0080 (18)	−0.0015 (19)
N17	0.013 (2)	0.014 (2)	0.030 (3)	0.0019 (19)	0.009 (2)	0.001 (2)
N27	0.021 (3)	0.014 (2)	0.022 (3)	−0.003 (2)	0.009 (2)	−0.002 (2)
C27	0.020 (3)	0.017 (3)	0.024 (3)	−0.003 (2)	0.007 (3)	−0.006 (2)
C21	0.022 (3)	0.014 (3)	0.020 (3)	−0.002 (2)	0.009 (2)	−0.005 (2)
C22	0.015 (3)	0.019 (3)	0.026 (3)	−0.002 (2)	0.008 (2)	−0.003 (2)
C23	0.020 (3)	0.016 (3)	0.024 (3)	0.001 (2)	0.009 (3)	0.002 (2)
C24	0.020 (3)	0.016 (3)	0.023 (3)	−0.003 (2)	0.010 (2)	0.001 (2)
Br24	0.0199 (3)	0.0163 (3)	0.0362 (4)	−0.0027 (2)	0.0099 (3)	0.0001 (3)
C25	0.017 (3)	0.023 (3)	0.020 (3)	0.001 (2)	0.009 (2)	0.000 (2)
C26	0.028 (3)	0.014 (3)	0.035 (4)	0.006 (2)	0.021 (3)	0.000 (3)
O2	0.017 (2)	0.030 (3)	0.030 (2)	0.0081 (19)	0.0045 (19)	−0.007 (2)
N31	0.028 (3)	0.020 (3)	0.025 (3)	−0.003 (2)	0.013 (2)	−0.003 (2)
C32	0.018 (3)	0.021 (3)	0.025 (3)	0.001 (2)	0.010 (2)	0.002 (2)
C33	0.017 (3)	0.020 (3)	0.018 (3)	0.002 (2)	0.007 (2)	0.003 (2)
C34	0.015 (3)	0.017 (3)	0.014 (3)	−0.002 (2)	0.004 (2)	0.000 (2)
C35	0.017 (3)	0.027 (3)	0.032 (3)	0.000 (3)	0.015 (3)	−0.003 (3)
C36	0.028 (3)	0.020 (3)	0.025 (3)	0.006 (3)	0.013 (3)	−0.001 (3)
C37	0.016 (3)	0.023 (3)	0.019 (3)	−0.003 (2)	0.009 (2)	−0.004 (2)
O3	0.014 (2)	0.025 (2)	0.033 (3)	−0.0021 (18)	0.0046 (19)	−0.003 (2)
N37	0.014 (2)	0.016 (2)	0.025 (3)	−0.0051 (19)	0.006 (2)	−0.006 (2)
N47	0.020 (2)	0.019 (3)	0.023 (3)	−0.007 (2)	0.011 (2)	−0.004 (2)
C47	0.018 (3)	0.018 (3)	0.025 (3)	−0.002 (2)	0.010 (2)	0.001 (2)
C41	0.022 (3)	0.019 (3)	0.023 (3)	−0.003 (2)	0.011 (3)	0.002 (2)
C42	0.018 (3)	0.019 (3)	0.024 (3)	−0.003 (2)	0.007 (2)	0.002 (2)
C43	0.020 (3)	0.019 (3)	0.024 (3)	−0.002 (2)	0.010 (3)	0.003 (2)
C44	0.021 (3)	0.020 (3)	0.022 (3)	−0.004 (2)	0.011 (2)	0.001 (2)
Br44	0.0260 (3)	0.0209 (3)	0.0341 (4)	−0.0077 (3)	0.0145 (3)	−0.0065 (3)
C45	0.014 (3)	0.027 (3)	0.023 (3)	−0.002 (2)	0.007 (2)	0.000 (3)
C46	0.030 (3)	0.015 (3)	0.027 (3)	0.003 (3)	0.015 (3)	0.003 (2)
O4	0.018 (2)	0.037 (3)	0.045 (3)	0.005 (2)	0.009 (2)	0.019 (2)

Geometric parameters (Å, º)

N11—C12	1.332 (8)	N31—C36	1.336 (9)
N11—C16	1.356 (8)	N31—C32	1.345 (8)
C12—C13	1.374 (9)	C32—C33	1.383 (9)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.399 (8)	C33—C34	1.386 (8)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.383 (8)	C34—C35	1.376 (9)
C14—C17	1.497 (8)	C34—C37	1.504 (8)
C15—C16	1.391 (9)	C35—C36	1.366 (9)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O1	1.240 (7)	C37—O3	1.228 (7)
C17—N17	1.352 (8)	C37—N37	1.349 (8)
N17—N27	1.385 (7)	N37—N47	1.377 (7)
N17—H17	0.88	N37—H37	0.88
N27—C27	1.290 (8)	N47—C47	1.282 (8)
C27—C21	1.474 (8)	C47—C41	1.475 (9)
C27—H27	0.95	C47—H47	0.95
C21—C22	1.392 (9)	C41—C46	1.394 (9)
C21—C26	1.418 (9)	C41—C42	1.409 (9)
C22—C23	1.378 (9)	C42—C43	1.393 (9)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.391 (9)	C43—C44	1.386 (9)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.379 (8)	C44—C45	1.388 (9)
C24—Br24	1.905 (6)	C44—Br44	1.898 (6)
C25—C26	1.366 (9)	C45—C46	1.379 (9)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
O2—H2A	1.00	O4—H4A	1.00
O2—H2B	1.00	O4—H4B	1.00
C12—N11—C16	115.7 (5)	C36—N31—C32	116.7 (6)
N11—C12—C13	125.7 (6)	N31—C32—C33	123.3 (6)
N11—C12—H12	117.2	N31—C32—H32	118.4
C13—C12—H12	117.2	C33—C32—H32	118.4
C12—C13—C14	117.9 (6)	C32—C33—C34	118.7 (6)
C12—C13—H13	121.1	C32—C33—H33	120.7
C14—C13—H13	121.1	C34—C33—H33	120.7
C15—C14—C13	118.3 (5)	C35—C34—C33	118.1 (6)
C15—C14—C17	117.0 (5)	C35—C34—C37	118.4 (5)
C13—C14—C17	124.6 (5)	C33—C34—C37	123.5 (6)
C14—C15—C16	119.0 (5)	C36—C35—C34	119.7 (6)
C14—C15—H15	120.5	C36—C35—H35	120.1
C16—C15—H15	120.5	C34—C35—H35	120.1
N11—C16—C15	123.4 (6)	N31—C36—C35	123.5 (6)
N11—C16—H16	118.3	N31—C36—H36	118.2
C15—C16—H16	118.3	C35—C36—H36	118.2
O1—C17—N17	123.6 (6)	O3—C37—N37	124.0 (6)
O1—C17—C14	120.6 (5)	O3—C37—C34	120.2 (6)
N17—C17—C14	115.8 (5)	N37—C37—C34	115.7 (5)
C17—N17—N27	118.9 (5)	C37—N37—N47	116.8 (5)
C17—N17—H17	120.6	C37—N37—H37	121.6
N27—N17—H17	120.6	N47—N37—H37	121.6
C27—N27—N17	114.2 (5)	C47—N47—N37	117.4 (5)
N27—C27—C21	121.0 (6)	N47—C47—C41	118.8 (6)
N27—C27—H27	119.5	N47—C47—H47	120.6
C21—C27—H27	119.5	C41—C47—H47	120.6
C22—C21—C26	118.4 (6)	C46—C41—C42	118.7 (6)
C22—C21—C27	118.7 (6)	C46—C41—C47	121.3 (6)
C26—C21—C27	122.9 (6)	C42—C41—C47	120.0 (6)
C23—C22—C21	121.5 (6)	C43—C42—C41	120.3 (6)
C23—C22—H22	119.2	C43—C42—H42	119.9
C21—C22—H22	119.2	C41—C42—H42	119.9
C22—C23—C24	118.4 (6)	C44—C43—C42	118.9 (6)
C22—C23—H23	120.8	C44—C43—H43	120.5
C24—C23—H23	120.8	C42—C43—H43	120.5
C25—C24—C23	121.6 (6)	C43—C44—C45	121.7 (6)
C25—C24—Br24	119.4 (5)	C43—C44—Br44	120.2 (5)
C23—C24—Br24	119.0 (5)	C45—C44—Br44	118.0 (5)
C26—C25—C24	120.0 (6)	C46—C45—C44	118.8 (6)
C26—C25—H25	120.0	C46—C45—H45	120.6
C24—C25—H25	120.0	C44—C45—H45	120.6
C25—C26—C21	120.1 (6)	C45—C46—C41	121.4 (6)
C25—C26—H26	119.9	C45—C46—H46	119.3
C21—C26—H26	119.9	C41—C46—H46	119.3
H2A—O2—H2B	105.4	H4A—O4—H4B	105.3
C16—N11—C12—C13	−1.9 (10)	C36—N31—C32—C33	−0.2 (10)
N11—C12—C13—C14	1.0 (10)	N31—C32—C33—C34	−0.1 (10)
C12—C13—C14—C15	2.2 (9)	C32—C33—C34—C35	−0.8 (9)
C12—C13—C14—C17	−178.1 (6)	C32—C33—C34—C37	−178.2 (6)
C13—C14—C15—C16	−4.2 (9)	C33—C34—C35—C36	2.0 (10)
C17—C14—C15—C16	176.1 (6)	C37—C34—C35—C36	179.5 (6)
C12—N11—C16—C15	−0.2 (10)	C32—N31—C36—C35	1.4 (10)
C14—C15—C16—N11	3.3 (10)	C34—C35—C36—N31	−2.3 (11)
C15—C14—C17—O1	23.3 (9)	C35—C34—C37—O3	−24.5 (9)
C13—C14—C17—O1	−156.4 (6)	C33—C34—C37—O3	152.9 (6)
C15—C14—C17—N17	−156.0 (6)	C35—C34—C37—N37	156.1 (6)
C13—C14—C17—N17	24.2 (9)	C33—C34—C37—N37	−26.6 (9)
O1—C17—N17—N27	−3.1 (9)	O3—C37—N37—N47	0.7 (9)
C14—C17—N17—N27	176.2 (5)	C34—C37—N37—N47	−179.9 (5)
C17—N17—N27—C27	−178.3 (6)	C37—N37—N47—C47	175.3 (6)
N17—N27—C27—C21	−179.8 (6)	N37—N47—C47—C41	−179.9 (6)
N27—C27—C21—C22	177.9 (6)	N47—C47—C41—C46	10.0 (10)
N27—C27—C21—C26	−3.9 (10)	N47—C47—C41—C42	−168.7 (6)
C26—C21—C22—C23	1.0 (10)	C46—C41—C42—C43	−3.9 (10)
C27—C21—C22—C23	179.3 (6)	C47—C41—C42—C43	174.7 (6)
C21—C22—C23—C24	−0.3 (10)	C41—C42—C43—C44	2.1 (10)
C22—C23—C24—C25	−0.5 (10)	C42—C43—C44—C45	1.0 (10)
C22—C23—C24—Br24	−178.2 (5)	C42—C43—C44—Br44	−177.8 (5)
C23—C24—C25—C26	0.6 (10)	C43—C44—C45—C46	−2.3 (10)
Br24—C24—C25—C26	178.3 (5)	Br44—C44—C45—C46	176.6 (5)
C24—C25—C26—C21	0.1 (10)	C44—C45—C46—C41	0.3 (10)
C22—C21—C26—C25	−0.9 (10)	C42—C41—C46—C45	2.7 (10)
C27—C21—C26—C25	−179.1 (6)	C47—C41—C46—C45	−175.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O2	0.88	2.03	2.864 (7)	159
N37—H37···O4	0.88	1.96	2.834 (7)	171
O2—H2A···O3	1.00	2.05	2.848 (7)	135
O2—H2A···N47	1.00	2.40	3.287 (7)	148
O2—H2B···N11^i	1.00	2.00	2.944 (7)	156
O4—H4A···N31^ii	1.00	1.85	2.789 (7)	155
O4—H4B···O1^iii	1.00	2.10	2.867 (7)	132
C13—H13···O2	0.95	2.48	3.327 (8)	149
C27—H27···O2	0.95	2.45	3.249 (8)	142
C33—H33···O4	0.95	2.45	3.191 (8)	135

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y+1/2, −z+1/2; (iii) x−1, −y+1/2, z−1/2.

(XI) N-isonicotinoyl 2-methoxybenzaldehydehydrazone

Crystal data

C14H13N3O2	F(000) = 1072
Mr = 255.27	Dx = 1.282 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6048 reflections
a = 9.8899 (3) Å	θ = 1.8–27.5°
b = 15.8189 (4) Å	µ = 0.09 mm^−1
c = 17.0380 (5) Å	T = 120 K
β = 97.236 (2)°	Needle, colourless
V = 2644.32 (13) Å^3	0.40 × 0.08 × 0.05 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	6048 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.8°
ϕ & ω scans	h = −12→12
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −20→20
Tmin = 0.974, Tmax = 0.996	l = −22→22
33120 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 0.7605P] where P = (Fo^2 + 2Fc^2)/3
6048 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.24285 (13)	0.46023 (9)	0.50833 (8)	0.0322 (3)
C12	0.32844 (16)	0.41087 (10)	0.47406 (9)	0.0283 (4)
C13	0.40675 (15)	0.43834 (9)	0.41718 (9)	0.0235 (3)
C14	0.39903 (15)	0.52289 (9)	0.39537 (9)	0.0218 (3)
C15	0.31165 (16)	0.57525 (10)	0.43039 (9)	0.0276 (4)
C16	0.23589 (16)	0.54106 (11)	0.48509 (10)	0.0325 (4)
C17	0.48363 (15)	0.56099 (9)	0.33778 (9)	0.0221 (3)
O1	0.53411 (11)	0.63194 (6)	0.34959 (6)	0.0274 (3)
N17	0.49667 (13)	0.51292 (8)	0.27459 (7)	0.0251 (3)
N27	0.57270 (13)	0.54065 (8)	0.21639 (8)	0.0261 (3)
C27	0.57442 (15)	0.48788 (10)	0.15936 (9)	0.0267 (4)
C21	0.64948 (15)	0.50540 (10)	0.09265 (9)	0.0264 (4)
C22	0.65393 (16)	0.44324 (10)	0.03400 (9)	0.0286 (4)
O22	0.58912 (12)	0.36911 (7)	0.04609 (7)	0.0355 (3)
C221	0.58917 (19)	0.30389 (12)	−0.01257 (11)	0.0441 (5)
C23	0.72338 (18)	0.45857 (12)	−0.03076 (10)	0.0369 (4)
C24	0.78696 (19)	0.53524 (12)	−0.03723 (11)	0.0437 (5)
C25	0.78403 (19)	0.59739 (12)	0.01980 (11)	0.0424 (5)
C26	0.71520 (17)	0.58195 (11)	0.08420 (10)	0.0334 (4)
N31	−0.07965 (14)	0.22436 (9)	0.07857 (9)	0.0349 (3)
C32	0.03832 (17)	0.18196 (11)	0.08414 (11)	0.0358 (4)
C33	0.15787 (16)	0.20838 (10)	0.12824 (10)	0.0293 (4)
C34	0.15779 (15)	0.28436 (9)	0.16890 (9)	0.0225 (3)
C35	0.03634 (15)	0.32914 (10)	0.16381 (9)	0.0265 (4)
C36	−0.07832 (16)	0.29678 (10)	0.11920 (10)	0.0310 (4)
C37	0.28144 (15)	0.32300 (9)	0.21527 (9)	0.0225 (3)
O3	0.28046 (10)	0.39774 (6)	0.23568 (6)	0.0286 (3)
N37	0.39079 (12)	0.27253 (8)	0.23228 (8)	0.0260 (3)
N47	0.51289 (12)	0.30839 (8)	0.26555 (7)	0.0253 (3)
C47	0.61228 (16)	0.25583 (10)	0.27639 (9)	0.0274 (4)
C41	0.75064 (15)	0.28293 (10)	0.30607 (9)	0.0262 (4)
C42	0.85552 (16)	0.22238 (10)	0.31390 (9)	0.0290 (4)
O42	0.81679 (11)	0.14148 (7)	0.29343 (7)	0.0373 (3)
C421	0.92104 (19)	0.08051 (11)	0.28666 (13)	0.0474 (5)
C43	0.98840 (17)	0.24604 (12)	0.34073 (10)	0.0358 (4)
C44	1.01772 (17)	0.32986 (12)	0.35887 (10)	0.0387 (4)
C45	0.91641 (17)	0.39039 (12)	0.35039 (10)	0.0370 (4)
C46	0.78383 (17)	0.36693 (11)	0.32432 (9)	0.0311 (4)
H12	0.3359	0.3533	0.4898	0.034*
H13	0.4642	0.4003	0.3937	0.028*
H15	0.3041	0.6335	0.4170	0.033*
H16	0.1747	0.5773	0.5078	0.039*
H17	0.4566	0.4632	0.2698	0.030*
H27	0.5257	0.4362	0.1605	0.032*
H22A	0.5466	0.3253	−0.0638	0.066*
H22B	0.5378	0.2550	0.0030	0.066*
H22C	0.6832	0.2869	−0.0169	0.066*
H23	0.7269	0.4164	−0.0702	0.044*
H24	0.8337	0.5457	−0.0817	0.052*
H25	0.8287	0.6499	0.0148	0.051*
H26	0.7128	0.6245	0.1234	0.040*
H32	0.0400	0.1303	0.0559	0.043*
H33	0.2383	0.1752	0.1306	0.035*
H35	0.0321	0.3815	0.1907	0.032*
H36	−0.1610	0.3278	0.1173	0.037*
H37	0.3850	0.2179	0.2225	0.031*
H47	0.5955	0.1977	0.2648	0.033*
H42A	0.9816	0.1011	0.2495	0.071*
H42B	0.8794	0.0271	0.2672	0.071*
H42C	0.9738	0.0714	0.3386	0.071*
H43	1.0589	0.2049	0.3466	0.043*
H44	1.1087	0.3459	0.3774	0.046*
H45	0.9378	0.4479	0.3624	0.044*
H46	0.7142	0.4086	0.3187	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0254 (7)	0.0439 (9)	0.0269 (8)	0.0010 (6)	0.0025 (6)	0.0029 (6)
C12	0.0279 (9)	0.0289 (9)	0.0267 (9)	−0.0040 (7)	−0.0023 (7)	0.0029 (7)
C13	0.0234 (8)	0.0228 (8)	0.0232 (8)	−0.0008 (6)	−0.0007 (6)	−0.0030 (6)
C14	0.0180 (7)	0.0252 (8)	0.0206 (8)	−0.0016 (6)	−0.0041 (6)	−0.0024 (6)
C15	0.0274 (9)	0.0269 (8)	0.0273 (9)	0.0044 (7)	−0.0017 (7)	0.0003 (7)
C16	0.0259 (9)	0.0426 (10)	0.0284 (9)	0.0081 (7)	0.0013 (7)	−0.0028 (8)
C17	0.0201 (8)	0.0202 (8)	0.0246 (8)	0.0008 (6)	−0.0025 (6)	0.0014 (6)
O1	0.0295 (6)	0.0216 (6)	0.0298 (6)	−0.0050 (5)	−0.0017 (5)	0.0008 (5)
N17	0.0285 (7)	0.0214 (7)	0.0262 (7)	−0.0067 (5)	0.0072 (6)	−0.0009 (6)
N27	0.0237 (7)	0.0293 (7)	0.0257 (7)	−0.0037 (5)	0.0041 (6)	0.0039 (6)
C27	0.0243 (8)	0.0279 (8)	0.0275 (9)	−0.0027 (7)	0.0016 (7)	0.0027 (7)
C21	0.0222 (8)	0.0324 (9)	0.0239 (8)	0.0003 (6)	0.0004 (7)	0.0045 (7)
C22	0.0234 (8)	0.0339 (9)	0.0276 (9)	0.0024 (7)	−0.0006 (7)	0.0054 (7)
O22	0.0371 (7)	0.0339 (7)	0.0363 (7)	−0.0028 (5)	0.0073 (6)	−0.0061 (5)
C221	0.0439 (11)	0.0432 (11)	0.0445 (11)	0.0015 (9)	0.0024 (9)	−0.0132 (9)
C23	0.0381 (10)	0.0460 (11)	0.0271 (9)	0.0054 (8)	0.0055 (8)	0.0000 (8)
C24	0.0454 (11)	0.0567 (12)	0.0311 (10)	−0.0025 (9)	0.0135 (9)	0.0091 (9)
C25	0.0436 (11)	0.0473 (11)	0.0373 (11)	−0.0106 (9)	0.0090 (9)	0.0085 (9)
C26	0.0341 (10)	0.0377 (10)	0.0283 (9)	−0.0046 (8)	0.0031 (8)	0.0026 (7)
N31	0.0255 (8)	0.0322 (8)	0.0453 (9)	−0.0034 (6)	−0.0017 (6)	−0.0044 (7)
C32	0.0287 (9)	0.0307 (9)	0.0469 (11)	−0.0030 (7)	0.0001 (8)	−0.0111 (8)
C33	0.0221 (8)	0.0287 (9)	0.0370 (10)	−0.0008 (7)	0.0030 (7)	−0.0059 (7)
C34	0.0211 (8)	0.0242 (8)	0.0223 (8)	−0.0024 (6)	0.0032 (6)	0.0010 (6)
C35	0.0253 (8)	0.0243 (8)	0.0299 (9)	−0.0006 (6)	0.0033 (7)	−0.0003 (7)
C36	0.0221 (8)	0.0303 (9)	0.0398 (10)	0.0025 (7)	0.0007 (7)	0.0030 (8)
C37	0.0221 (8)	0.0243 (8)	0.0217 (8)	−0.0013 (6)	0.0051 (6)	−0.0017 (6)
O3	0.0249 (6)	0.0237 (6)	0.0366 (7)	−0.0001 (4)	0.0018 (5)	−0.0076 (5)
N37	0.0221 (7)	0.0220 (7)	0.0328 (8)	−0.0020 (5)	−0.0010 (6)	−0.0066 (6)
N47	0.0198 (7)	0.0291 (7)	0.0267 (7)	−0.0030 (6)	0.0020 (6)	−0.0055 (6)
C47	0.0264 (9)	0.0270 (8)	0.0282 (9)	−0.0012 (7)	0.0011 (7)	−0.0042 (7)
C41	0.0233 (8)	0.0339 (9)	0.0211 (8)	−0.0022 (7)	0.0012 (7)	−0.0023 (7)
C42	0.0269 (9)	0.0349 (9)	0.0249 (9)	−0.0024 (7)	0.0019 (7)	0.0033 (7)
O42	0.0255 (6)	0.0319 (7)	0.0538 (8)	0.0028 (5)	0.0021 (6)	0.0039 (6)
C421	0.0348 (11)	0.0341 (10)	0.0735 (15)	0.0086 (8)	0.0076 (10)	0.0063 (10)
C43	0.0244 (9)	0.0505 (11)	0.0323 (10)	0.0018 (8)	0.0030 (7)	0.0058 (8)
C44	0.0251 (9)	0.0578 (12)	0.0326 (10)	−0.0106 (8)	0.0010 (8)	−0.0050 (9)
C45	0.0332 (10)	0.0451 (11)	0.0332 (10)	−0.0126 (8)	0.0063 (8)	−0.0104 (8)
C46	0.0290 (9)	0.0368 (10)	0.0276 (9)	−0.0032 (7)	0.0038 (7)	−0.0081 (7)

Geometric parameters (Å, º)

N11—C16	1.338 (2)	N31—C36	1.338 (2)
N11—C12	1.339 (2)	N31—C32	1.339 (2)
C12—C13	1.385 (2)	C32—C33	1.383 (2)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.388 (2)	C33—C34	1.387 (2)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.385 (2)	C34—C35	1.388 (2)
C14—C17	1.494 (2)	C34—C37	1.500 (2)
C15—C16	1.378 (2)	C35—C36	1.382 (2)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O1	1.2346 (17)	C37—O3	1.2327 (17)
C17—N17	1.3374 (19)	C37—N37	1.3461 (19)
N17—N27	1.3889 (16)	N37—N47	1.3889 (17)
N17—H17	0.88	N37—H37	0.88
N27—C27	1.2827 (19)	N47—C47	1.2829 (19)
C27—C21	1.460 (2)	C47—C41	1.462 (2)
C27—H27	0.95	C47—H47	0.95
C21—C26	1.390 (2)	C41—C46	1.394 (2)
C21—C22	1.407 (2)	C41—C42	1.406 (2)
C22—O22	1.3645 (19)	C42—O42	1.3685 (19)
C22—C23	1.392 (2)	C42—C43	1.387 (2)
O22—C221	1.437 (2)	O42—C421	1.427 (2)
C221—H22A	0.98	C421—H42A	0.98
C221—H22B	0.98	C421—H42B	0.98
C221—H22C	0.98	C421—H42C	0.98
C23—C24	1.377 (3)	C43—C44	1.384 (3)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.385 (3)	C44—C45	1.380 (2)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.384 (2)	C45—C46	1.381 (2)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C16—N11—C12	116.11 (14)	C36—N31—C32	116.15 (14)
N11—C12—C13	124.24 (15)	N31—C32—C33	124.39 (15)
N11—C12—H12	117.9	N31—C32—H32	117.8
C13—C12—H12	117.9	C33—C32—H32	117.8
C12—C13—C14	118.23 (14)	C32—C33—C34	118.61 (15)
C12—C13—H13	120.9	C32—C33—H33	120.7
C14—C13—H13	120.9	C34—C33—H33	120.7
C15—C14—C13	118.51 (14)	C33—C34—C35	117.77 (14)
C15—C14—C17	118.23 (13)	C33—C34—C37	124.36 (13)
C13—C14—C17	123.24 (13)	C35—C34—C37	117.83 (13)
C16—C15—C14	118.59 (15)	C36—C35—C34	119.30 (14)
C16—C15—H15	120.7	C36—C35—H35	120.4
C14—C15—H15	120.7	C34—C35—H35	120.4
N11—C16—C15	124.29 (15)	N31—C36—C35	123.77 (15)
N11—C16—H16	117.9	N31—C36—H36	118.1
C15—C16—H16	117.9	C35—C36—H36	118.1
O1—C17—N17	124.75 (14)	O3—C37—N37	122.87 (14)
O1—C17—C14	120.53 (13)	O3—C37—C34	120.30 (14)
N17—C17—C14	114.71 (13)	N37—C37—C34	116.83 (13)
C17—N17—N27	120.73 (12)	C37—N37—N47	118.64 (12)
C17—N17—H17	119.6	C37—N37—H37	120.7
N27—N17—H17	119.6	N47—N37—H37	120.7
C27—N27—N17	113.30 (12)	C47—N47—N37	113.89 (12)
N27—C27—C21	121.52 (14)	N47—C47—C41	121.77 (14)
N27—C27—H27	119.2	N47—C47—H47	119.1
C21—C27—H27	119.2	C41—C47—H47	119.1
C26—C21—C22	118.58 (14)	C46—C41—C42	118.55 (15)
C26—C21—C27	122.41 (15)	C46—C41—C47	122.70 (15)
C22—C21—C27	119.00 (14)	C42—C41—C47	118.71 (14)
O22—C22—C23	123.87 (15)	O42—C42—C43	124.01 (15)
O22—C22—C21	115.86 (13)	O42—C42—C41	115.69 (14)
C23—C22—C21	120.26 (15)	C43—C42—C41	120.30 (15)
C22—O22—C221	118.09 (13)	C42—O42—C421	118.09 (13)
O22—C221—H22A	109.5	O42—C421—H42A	109.5
O22—C221—H22B	109.5	O42—C421—H42B	109.5
H22A—C221—H22B	109.5	H42A—C421—H42B	109.5
O22—C221—H22C	109.5	O42—C421—H42C	109.5
H22A—C221—H22C	109.5	H42A—C421—H42C	109.5
H22B—C221—H22C	109.5	H42B—C421—H42C	109.5
C24—C23—C22	119.52 (16)	C44—C43—C42	119.68 (16)
C24—C23—H23	120.2	C44—C43—H43	120.2
C22—C23—H23	120.2	C42—C43—H43	120.2
C23—C24—C25	121.25 (16)	C45—C44—C43	120.82 (16)
C23—C24—H24	119.4	C45—C44—H44	119.6
C25—C24—H24	119.4	C43—C44—H44	119.6
C26—C25—C24	119.14 (17)	C44—C45—C46	119.63 (17)
C26—C25—H25	120.4	C44—C45—H45	120.2
C24—C25—H25	120.4	C46—C45—H45	120.2
C25—C26—C21	121.25 (16)	C45—C46—C41	121.01 (16)
C25—C26—H26	119.4	C45—C46—H46	119.5
C21—C26—H26	119.4	C41—C46—H46	119.5
C16—N11—C12—C13	−0.5 (2)	C36—N31—C32—C33	−0.1 (3)
N11—C12—C13—C14	1.6 (2)	N31—C32—C33—C34	−0.9 (3)
C12—C13—C14—C15	−1.2 (2)	C32—C33—C34—C35	0.9 (2)
C12—C13—C14—C17	176.82 (14)	C32—C33—C34—C37	−176.50 (15)
C13—C14—C15—C16	−0.2 (2)	C33—C34—C35—C36	0.1 (2)
C17—C14—C15—C16	−178.35 (14)	C37—C34—C35—C36	177.68 (14)
C12—N11—C16—C15	−1.1 (2)	C32—N31—C36—C35	1.2 (2)
C14—C15—C16—N11	1.5 (3)	C34—C35—C36—N31	−1.2 (2)
C15—C14—C17—O1	38.7 (2)	C33—C34—C37—O3	164.71 (14)
C13—C14—C17—O1	−139.36 (15)	C35—C34—C37—O3	−12.7 (2)
C15—C14—C17—N17	−140.50 (14)	C33—C34—C37—N37	−14.9 (2)
C13—C14—C17—N17	41.5 (2)	C35—C34—C37—N37	167.71 (13)
O1—C17—N17—N27	0.9 (2)	O3—C37—N37—N47	−8.2 (2)
C14—C17—N17—N27	−179.96 (12)	C34—C37—N37—N47	171.40 (12)
C17—N17—N27—C27	−179.37 (14)	C37—N37—N47—C47	−177.15 (13)
N17—N27—C27—C21	−179.69 (13)	N37—N47—C47—C41	176.01 (13)
N27—C27—C21—C26	−4.5 (2)	N47—C47—C41—C46	−0.1 (2)
N27—C27—C21—C22	176.53 (15)	N47—C47—C41—C42	−177.80 (14)
C26—C21—C22—O22	179.18 (14)	C46—C41—C42—O42	−178.61 (14)
C27—C21—C22—O22	−1.8 (2)	C47—C41—C42—O42	−0.8 (2)
C26—C21—C22—C23	0.2 (2)	C46—C41—C42—C43	1.2 (2)
C27—C21—C22—C23	179.24 (15)	C47—C41—C42—C43	179.02 (14)
C23—C22—O22—C221	−1.9 (2)	C43—C42—O42—C421	−10.8 (2)
C21—C22—O22—C221	179.24 (14)	C41—C42—O42—C421	169.09 (15)
O22—C22—C23—C24	−179.26 (16)	O42—C42—C43—C44	179.04 (15)
C21—C22—C23—C24	−0.4 (3)	C41—C42—C43—C44	−0.8 (2)
C22—C23—C24—C25	0.5 (3)	C42—C43—C44—C45	−0.2 (3)
C23—C24—C25—C26	−0.3 (3)	C43—C44—C45—C46	0.7 (3)
C24—C25—C26—C21	0.1 (3)	C44—C45—C46—C41	−0.3 (3)
C22—C21—C26—C25	−0.1 (2)	C42—C41—C46—C45	−0.7 (2)
C27—C21—C26—C25	−179.07 (16)	C47—C41—C46—C45	−178.40 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O3	0.88	2.05	2.8240 (16)	146
N17—H17···N47	0.88	2.51	3.2440 (18)	141
N37—H37···O1^i	0.88	2.06	2.7757 (16)	138
C33—H33···O1^i	0.95	2.34	3.2550 (19)	163
C47—H47···O1^i	0.95	2.43	3.1244 (19)	130

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(XII) N-isonicotinoyl 3-methoxybenzaldehydehydrazone

Crystal data

C14H13N3O2	F(000) = 536
Mr = 255.27	Dx = 1.371 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2827 reflections
a = 8.2938 (4) Å	θ = 2.4–27.5°
b = 11.0771 (6) Å	µ = 0.10 mm^−1
c = 13.846 (5) Å	T = 120 K
β = 103.478 (3)°	Plate, colourless
V = 1237.0 (5) Å^3	0.15 × 0.15 × 0.04 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2827 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.4°
ϕ & ω scans	h = −10→10
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.977, Tmax = 0.996	l = −17→17
14906 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0889P)^2] where P = (Fo^2 + 2Fc^2)/3
2827 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.3443 (2)	0.01173 (16)	0.21674 (11)	0.0221 (4)
C12	0.2510 (2)	0.11174 (19)	0.21241 (14)	0.0229 (5)
C13	0.2721 (2)	0.19592 (18)	0.28839 (13)	0.0209 (5)
C14	0.3938 (2)	0.17631 (17)	0.37461 (13)	0.0185 (4)
C15	0.4922 (2)	0.07418 (19)	0.37889 (14)	0.0217 (5)
C16	0.4640 (2)	−0.00431 (19)	0.29901 (14)	0.0224 (5)
C17	0.4226 (2)	0.25532 (19)	0.46606 (13)	0.0198 (5)
O1	0.51981 (18)	0.22403 (13)	0.54261 (10)	0.0292 (4)
N17	0.3325 (2)	0.35815 (15)	0.45832 (11)	0.0202 (4)
N27	0.3498 (2)	0.43143 (15)	0.54134 (11)	0.0200 (4)
C27	0.2485 (2)	0.51952 (18)	0.53219 (14)	0.0208 (5)
C21	0.2499 (2)	0.60431 (18)	0.61353 (13)	0.0195 (5)
C22	0.3668 (2)	0.59741 (18)	0.70439 (14)	0.0205 (5)
C23	0.3612 (2)	0.68102 (19)	0.77832 (14)	0.0236 (5)
O23	0.46807 (18)	0.68502 (15)	0.86998 (10)	0.0329 (4)
C231	0.5981 (3)	0.6000 (2)	0.89170 (16)	0.0332 (6)
C24	0.2401 (3)	0.77063 (19)	0.76175 (15)	0.0275 (5)
C25	0.1266 (3)	0.7769 (2)	0.67251 (15)	0.0284 (5)
C26	0.1297 (3)	0.69469 (19)	0.59773 (15)	0.0247 (5)
H12	0.1662	0.1254	0.1542	0.027*
H13	0.2043	0.2660	0.2816	0.025*
H15	0.5781	0.0584	0.4361	0.026*
H16	0.5333	−0.0733	0.3028	0.027*
H17	0.2644	0.3781	0.4018	0.024*
H27	0.1699	0.5305	0.4709	0.025*
H22	0.4493	0.5361	0.7154	0.025*
H23A	0.5520	0.5191	0.8953	0.040*
H23B	0.6729	0.6199	0.9556	0.040*
H23C	0.6598	0.6018	0.8393	0.040*
H24	0.2361	0.8275	0.8125	0.033*
H25	0.0447	0.8386	0.6618	0.034*
H26	0.0505	0.6998	0.5361	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0256 (9)	0.0214 (10)	0.0178 (8)	−0.0019 (7)	0.0020 (7)	−0.0010 (7)
C12	0.0264 (11)	0.0228 (12)	0.0166 (9)	0.0010 (9)	−0.0009 (8)	0.0042 (8)
C13	0.0248 (11)	0.0170 (11)	0.0192 (9)	0.0017 (9)	0.0015 (8)	0.0012 (8)
C14	0.0204 (10)	0.0166 (11)	0.0183 (9)	−0.0034 (8)	0.0041 (8)	−0.0006 (8)
C15	0.0212 (10)	0.0220 (12)	0.0196 (9)	0.0007 (9)	0.0001 (8)	0.0003 (8)
C16	0.0244 (10)	0.0199 (11)	0.0222 (10)	0.0019 (9)	0.0038 (8)	0.0002 (8)
C17	0.0225 (10)	0.0175 (11)	0.0186 (10)	−0.0017 (9)	0.0031 (8)	0.0003 (8)
O1	0.0381 (9)	0.0237 (8)	0.0196 (7)	0.0059 (7)	−0.0058 (6)	−0.0031 (6)
N17	0.0266 (9)	0.0190 (9)	0.0130 (8)	0.0023 (7)	0.0008 (7)	−0.0023 (7)
N27	0.0272 (9)	0.0172 (9)	0.0156 (8)	−0.0024 (7)	0.0048 (7)	−0.0022 (7)
C27	0.0260 (10)	0.0213 (11)	0.0143 (9)	−0.0008 (9)	0.0029 (8)	0.0021 (8)
C21	0.0238 (10)	0.0167 (11)	0.0196 (10)	−0.0022 (8)	0.0078 (8)	0.0012 (8)
C22	0.0217 (10)	0.0198 (11)	0.0204 (10)	−0.0004 (9)	0.0059 (8)	−0.0015 (8)
C23	0.0247 (11)	0.0249 (12)	0.0215 (10)	−0.0023 (9)	0.0059 (8)	−0.0027 (8)
O23	0.0325 (8)	0.0375 (10)	0.0245 (8)	0.0061 (7)	−0.0020 (6)	−0.0129 (7)
C231	0.0346 (12)	0.0341 (14)	0.0255 (11)	0.0022 (11)	−0.0041 (9)	−0.0074 (10)
C24	0.0360 (12)	0.0220 (12)	0.0268 (11)	−0.0001 (10)	0.0119 (9)	−0.0072 (9)
C25	0.0337 (12)	0.0222 (12)	0.0313 (12)	0.0057 (10)	0.0114 (10)	0.0005 (9)
C26	0.0287 (11)	0.0239 (12)	0.0211 (10)	0.0023 (9)	0.0051 (8)	0.0049 (8)

Geometric parameters (Å, º)

N11—C16	1.337 (2)	C27—H27	0.95
N11—C12	1.345 (3)	C21—C26	1.394 (3)
C12—C13	1.386 (3)	C21—C22	1.400 (3)
C12—H12	0.95	C22—C23	1.389 (3)
C13—C14	1.389 (3)	C22—H22	0.95
C13—H13	0.95	C23—O23	1.369 (2)
C14—C15	1.388 (3)	C23—C24	1.393 (3)
C14—C17	1.512 (3)	O23—C231	1.411 (3)
C15—C16	1.383 (3)	C231—H23A	0.98
C15—H15	0.95	C231—H23B	0.98
C16—H16	0.95	C231—H23C	0.98
C17—O1	1.223 (2)	C24—C25	1.369 (3)
C17—N17	1.353 (3)	C24—H24	0.95
N17—N27	1.387 (2)	C25—C26	1.384 (3)
N17—H17	0.88	C25—H25	0.95
N27—C27	1.275 (3)	C26—H26	0.95
C27—C21	1.465 (3)
C16—N11—C12	116.92 (16)	C26—C21—C22	120.04 (18)
N11—C12—C13	123.44 (17)	C26—C21—C27	117.57 (17)
N11—C12—H12	118.3	C22—C21—C27	122.39 (18)
C13—C12—H12	118.3	C23—C22—C21	119.37 (19)
C12—C13—C14	119.01 (18)	C23—C22—H22	120.3
C12—C13—H13	120.5	C21—C22—H22	120.3
C14—C13—H13	120.5	O23—C23—C22	125.37 (18)
C15—C14—C13	117.80 (17)	O23—C23—C24	114.58 (17)
C15—C14—C17	117.36 (16)	C22—C23—C24	120.05 (18)
C13—C14—C17	124.80 (18)	C23—O23—C231	118.28 (15)
C16—C15—C14	119.33 (17)	O23—C231—H23A	109.5
C16—C15—H15	120.3	O23—C231—H23B	109.5
C14—C15—H15	120.3	H23A—C231—H23B	109.5
N11—C16—C15	123.47 (19)	O23—C231—H23C	109.5
N11—C16—H16	118.3	H23A—C231—H23C	109.5
C15—C16—H16	118.3	H23B—C231—H23C	109.5
O1—C17—N17	123.21 (17)	C25—C24—C23	120.17 (19)
O1—C17—C14	120.36 (18)	C25—C24—H24	119.9
N17—C17—C14	116.40 (15)	C23—C24—H24	119.9
C17—N17—N27	118.59 (15)	C24—C25—C26	120.8 (2)
C17—N17—H17	120.7	C24—C25—H25	119.6
N27—N17—H17	120.7	C26—C25—H25	119.6
C27—N27—N17	115.28 (15)	C25—C26—C21	119.53 (19)
N27—C27—C21	121.85 (17)	C25—C26—H26	120.2
N27—C27—H27	119.1	C21—C26—H26	120.2
C21—C27—H27	119.1
C16—N11—C12—C13	−0.8 (3)	N17—N27—C27—C21	179.40 (17)
N11—C12—C13—C14	−1.0 (3)	N27—C27—C21—C26	−177.36 (19)
C12—C13—C14—C15	2.0 (3)	N27—C27—C21—C22	3.0 (3)
C12—C13—C14—C17	−175.39 (18)	C26—C21—C22—C23	0.2 (3)
C13—C14—C15—C16	−1.1 (3)	C27—C21—C22—C23	179.86 (18)
C17—C14—C15—C16	176.41 (18)	C21—C22—C23—O23	−179.60 (18)
C12—N11—C16—C15	1.7 (3)	C21—C22—C23—C24	0.0 (3)
C14—C15—C16—N11	−0.7 (3)	C22—C23—O23—C231	1.8 (3)
C15—C14—C17—O1	−5.7 (3)	C24—C23—O23—C231	−177.87 (19)
C13—C14—C17—O1	171.67 (19)	O23—C23—C24—C25	179.40 (18)
C15—C14—C17—N17	176.09 (18)	C22—C23—C24—C25	−0.2 (3)
C13—C14—C17—N17	−6.6 (3)	C23—C24—C25—C26	0.2 (3)
O1—C17—N17—N27	−0.6 (3)	C24—C25—C26—C21	0.0 (3)
C14—C17—N17—N27	177.58 (16)	C22—C21—C26—C25	−0.3 (3)
C17—N17—N27—C27	−172.55 (18)	C27—C21—C26—C25	−179.89 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N11^i	0.88	2.24	3.044 (2)	152
C12—H12···O1^ii	0.95	2.40	3.227 (2)	145
C24—H24···N27^iii	0.95	2.57	3.480 (3)	161
C27—H27···N11^i	0.95	2.58	3.353 (3)	139
C16—H16···Cg2^iv	0.95	2.92	3.689 (2)	139

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x+1/2, −y+1/2, z−1/2.

(XIII) N-isonicotinoyl 4-methoxybenzaldehydehydrazone

Crystal data

C14H13N3O2·H2O	F(000) = 576
Mr = 273.29	Dx = 1.389 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3002 reflections
a = 7.2702 (2) Å	θ = 3.2–27.6°
b = 12.3085 (5) Å	µ = 0.10 mm^−1
c = 14.7299 (6) Å	T = 120 K
β = 97.370 (3)°	Plate, colourless
V = 1307.22 (8) Å^3	0.36 × 0.18 × 0.05 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	3002 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2550 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.2°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −15→15
Tmin = 0.972, Tmax = 0.995	l = −18→19
14720 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 1.3161P] where P = (Fo^2 + 2Fc^2)/3
3002 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.3674 (2)	0.64170 (15)	0.00512 (11)	0.0273 (4)
C12	0.4632 (3)	0.67382 (16)	0.08417 (13)	0.0237 (4)
C13	0.4656 (3)	0.61667 (15)	0.16551 (13)	0.0209 (4)
C14	0.3664 (3)	0.52034 (15)	0.16538 (13)	0.0207 (4)
C15	0.2717 (3)	0.48411 (17)	0.08244 (14)	0.0261 (4)
C16	0.2755 (3)	0.54703 (18)	0.00512 (14)	0.0290 (5)
C17	0.3516 (3)	0.45384 (16)	0.24959 (13)	0.0210 (4)
O1	0.3476 (2)	0.35389 (11)	0.24625 (10)	0.0270 (3)
N17	0.3351 (2)	0.51258 (13)	0.32488 (10)	0.0210 (3)
N27	0.2966 (2)	0.46005 (13)	0.40326 (10)	0.0215 (3)
C27	0.2743 (3)	0.52519 (16)	0.46882 (13)	0.0213 (4)
C21	0.2229 (2)	0.48909 (15)	0.55672 (12)	0.0201 (4)
C22	0.2154 (3)	0.56569 (16)	0.62589 (13)	0.0219 (4)
C23	0.1626 (3)	0.53758 (16)	0.70939 (13)	0.0227 (4)
C24	0.1133 (2)	0.43093 (15)	0.72535 (12)	0.0198 (4)
O24	0.06597 (19)	0.41100 (11)	0.81042 (9)	0.0239 (3)
C241	0.0145 (3)	0.30219 (16)	0.83091 (13)	0.0249 (4)
C25	0.1180 (3)	0.35286 (15)	0.65724 (12)	0.0206 (4)
C26	0.1735 (3)	0.38237 (15)	0.57379 (13)	0.0211 (4)
O2	0.3743 (2)	0.74712 (11)	0.34021 (9)	0.0268 (3)
H12	0.5332	0.7390	0.0846	0.028*
H13	0.5340	0.6430	0.2204	0.025*
H15	0.2057	0.4173	0.0793	0.031*
H16	0.2098	0.5221	−0.0509	0.035*
H17	0.3485	0.5836	0.3244	0.025*
H27	0.2920	0.6007	0.4599	0.026*
H22	0.2474	0.6390	0.6152	0.026*
H23	0.1599	0.5909	0.7558	0.027*
H24A	−0.0941	0.2803	0.7884	0.037*
H24B	−0.0156	0.2989	0.8938	0.037*
H24C	0.1180	0.2529	0.8245	0.037*
H25	0.0835	0.2799	0.6677	0.025*
H26	0.1778	0.3289	0.5276	0.025*
H2A	0.3661	0.7824	0.3930	0.040*
H2B	0.4660	0.7794	0.3145	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0303 (9)	0.0298 (9)	0.0225 (8)	0.0076 (7)	0.0063 (7)	0.0018 (7)
C12	0.0238 (9)	0.0211 (9)	0.0276 (10)	0.0041 (7)	0.0080 (7)	0.0012 (8)
C13	0.0208 (9)	0.0209 (9)	0.0214 (9)	0.0029 (7)	0.0043 (7)	−0.0029 (7)
C14	0.0214 (9)	0.0189 (9)	0.0222 (9)	0.0042 (7)	0.0042 (7)	−0.0018 (7)
C15	0.0270 (10)	0.0235 (10)	0.0277 (10)	0.0008 (8)	0.0036 (8)	−0.0061 (8)
C16	0.0305 (10)	0.0333 (11)	0.0224 (10)	0.0042 (9)	0.0010 (8)	−0.0045 (8)
C17	0.0191 (9)	0.0197 (9)	0.0251 (9)	−0.0010 (7)	0.0057 (7)	−0.0001 (7)
O1	0.0360 (8)	0.0159 (7)	0.0311 (8)	−0.0022 (6)	0.0118 (6)	−0.0014 (5)
N17	0.0266 (8)	0.0167 (8)	0.0206 (8)	0.0005 (6)	0.0070 (6)	0.0022 (6)
N27	0.0244 (8)	0.0214 (8)	0.0189 (8)	0.0009 (6)	0.0034 (6)	0.0026 (6)
C27	0.0225 (9)	0.0184 (9)	0.0230 (9)	0.0005 (7)	0.0034 (7)	0.0025 (7)
C21	0.0184 (8)	0.0204 (9)	0.0218 (9)	0.0031 (7)	0.0030 (7)	0.0041 (7)
C22	0.0240 (9)	0.0169 (9)	0.0247 (9)	−0.0014 (7)	0.0028 (7)	0.0030 (7)
C23	0.0282 (10)	0.0188 (9)	0.0211 (9)	−0.0005 (7)	0.0034 (7)	−0.0018 (7)
C24	0.0208 (9)	0.0212 (9)	0.0171 (8)	0.0015 (7)	0.0017 (7)	0.0017 (7)
O24	0.0338 (8)	0.0214 (7)	0.0175 (6)	−0.0005 (6)	0.0070 (5)	0.0010 (5)
C241	0.0315 (10)	0.0217 (10)	0.0226 (9)	0.0015 (8)	0.0082 (8)	0.0038 (7)
C25	0.0247 (9)	0.0163 (9)	0.0208 (9)	−0.0009 (7)	0.0026 (7)	0.0016 (7)
C26	0.0263 (9)	0.0171 (9)	0.0199 (9)	0.0029 (7)	0.0033 (7)	−0.0014 (7)
O2	0.0378 (8)	0.0195 (7)	0.0249 (7)	−0.0032 (6)	0.0104 (6)	−0.0018 (5)

Geometric parameters (Å, º)

N11—C12	1.338 (3)	C21—C26	1.393 (3)
N11—C16	1.343 (3)	C21—C22	1.394 (3)
C12—C13	1.388 (3)	C22—C23	1.379 (3)
C12—H12	0.95	C22—H22	0.95
C13—C14	1.388 (3)	C23—C24	1.389 (3)
C13—H13	0.95	C23—H23	0.95
C14—C15	1.396 (3)	C24—O24	1.364 (2)
C14—C17	1.501 (3)	C24—C25	1.393 (3)
C15—C16	1.381 (3)	O24—C241	1.433 (2)
C15—H15	0.95	C241—H24A	0.98
C16—H16	0.95	C241—H24B	0.98
C17—O1	1.231 (2)	C241—H24C	0.98
C17—N17	1.342 (2)	C25—C26	1.390 (3)
N17—N27	1.383 (2)	C25—H25	0.95
N17—H17	0.88	C26—H26	0.95
N27—C27	1.281 (2)	O2—H2A	0.9001
C27—C21	1.462 (3)	O2—H2B	0.90
C27—H27	0.95
C12—N11—C16	117.38 (17)	C26—C21—C22	118.06 (17)
N11—C12—C13	123.32 (19)	C26—C21—C27	123.20 (17)
N11—C12—H12	118.3	C22—C21—C27	118.69 (17)
C13—C12—H12	118.3	C23—C22—C21	121.58 (18)
C12—C13—C14	118.88 (18)	C23—C22—H22	119.2
C12—C13—H13	120.6	C21—C22—H22	119.2
C14—C13—H13	120.6	C22—C23—C24	119.71 (17)
C13—C14—C15	118.16 (18)	C22—C23—H23	120.1
C13—C14—C17	123.84 (17)	C24—C23—H23	120.1
C15—C14—C17	117.98 (17)	O24—C24—C23	115.25 (16)
C16—C15—C14	118.87 (19)	O24—C24—C25	124.76 (17)
C16—C15—H15	120.6	C23—C24—C25	119.98 (17)
C14—C15—H15	120.6	C24—O24—C241	117.72 (15)
N11—C16—C15	123.32 (19)	O24—C241—H24A	109.5
N11—C16—H16	118.3	O24—C241—H24B	109.5
C15—C16—H16	118.3	H24A—C241—H24B	109.5
O1—C17—N17	124.53 (18)	O24—C241—H24C	109.5
O1—C17—C14	121.04 (17)	H24A—C241—H24C	109.5
N17—C17—C14	114.35 (16)	H24B—C241—H24C	109.5
C17—N17—N27	119.16 (16)	C26—C25—C24	119.55 (17)
C17—N17—H17	120.4	C26—C25—H25	120.2
N27—N17—H17	120.4	C24—C25—H25	120.2
C27—N27—N17	113.30 (16)	C25—C26—C21	121.12 (17)
N27—C27—C21	123.29 (18)	C25—C26—H26	119.4
N27—C27—H27	118.4	C21—C26—H26	119.4
C21—C27—H27	118.4	H2A—O2—H2B	106.6
C16—N11—C12—C13	−2.6 (3)	N17—N27—C27—C21	176.68 (16)
N11—C12—C13—C14	1.0 (3)	N27—C27—C21—C26	−7.4 (3)
C12—C13—C14—C15	1.4 (3)	N27—C27—C21—C22	175.35 (18)
C12—C13—C14—C17	−177.31 (17)	C26—C21—C22—C23	0.6 (3)
C13—C14—C15—C16	−2.1 (3)	C27—C21—C22—C23	178.05 (17)
C17—C14—C15—C16	176.65 (18)	C21—C22—C23—C24	−0.8 (3)
C12—N11—C16—C15	1.8 (3)	C22—C23—C24—O24	179.07 (16)
C14—C15—C16—N11	0.5 (3)	C22—C23—C24—C25	0.2 (3)
C13—C14—C17—O1	−144.08 (19)	C23—C24—O24—C241	−179.78 (17)
C15—C14—C17—O1	37.2 (3)	C25—C24—O24—C241	−1.0 (3)
C13—C14—C17—N17	38.9 (3)	O24—C24—C25—C26	−178.26 (17)
C15—C14—C17—N17	−139.85 (18)	C23—C24—C25—C26	0.5 (3)
O1—C17—N17—N27	−5.2 (3)	C24—C25—C26—C21	−0.6 (3)
C14—C17—N17—N27	171.75 (15)	C22—C21—C26—C25	0.1 (3)
C17—N17—N27—C27	−176.47 (17)	C27—C21—C26—C25	−177.21 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O2	0.88	2.03	2.907 (2)	173
O2—H2A···N11^i	0.90	1.90	2.794 (2)	176
O2—H2B···O1^ii	0.90	1.95	2.846 (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

Crystal data

C15H15N3O2	F(000) = 1136
Mr = 269.30	Dx = 1.310 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6259 reflections
a = 8.3787 (3) Å	θ = 2.5–27.5°
b = 18.2450 (7) Å	µ = 0.09 mm^−1
c = 17.8701 (7) Å	T = 120 K
β = 90.975 (2)°	Block, colourless
V = 2731.40 (18) Å^3	0.15 × 0.10 × 0.10 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	6259 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.101
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
ϕ & ω scans	h = −10→10
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −23→23
Tmin = 0.977, Tmax = 0.991	l = −20→23
36314 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0646P)^2] where P = (Fo^2 + 2Fc^2)/3
6259 reflections	(Δ/σ)max < 0.001
363 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.2340 (2)	0.47253 (11)	−0.01027 (11)	0.0480 (5)
C12	0.3231 (3)	0.42644 (12)	0.02971 (13)	0.0438 (6)
C13	0.4060 (2)	0.44493 (11)	0.09511 (12)	0.0373 (5)
C14	0.4000 (2)	0.51669 (10)	0.11968 (12)	0.0330 (5)
C15	0.3099 (2)	0.56605 (12)	0.07790 (13)	0.0436 (6)
C16	0.2294 (3)	0.54137 (13)	0.01526 (14)	0.0499 (6)
C17	0.4894 (2)	0.54463 (11)	0.18730 (12)	0.0343 (5)
O1	0.54021 (16)	0.60796 (7)	0.18926 (9)	0.0445 (4)
N17	0.50727 (19)	0.49675 (8)	0.24398 (10)	0.0363 (4)
N27	0.58615 (19)	0.51937 (9)	0.30882 (10)	0.0382 (4)
C27	0.5863 (2)	0.47283 (11)	0.36289 (12)	0.0370 (5)
C21	0.6655 (2)	0.49102 (11)	0.43347 (12)	0.0357 (5)
C22	0.6866 (2)	0.43837 (11)	0.48994 (12)	0.0367 (5)
O22	0.62164 (15)	0.37096 (7)	0.47492 (8)	0.0407 (4)
C221	0.6323 (3)	0.31602 (11)	0.53255 (13)	0.0456 (6)
C222	0.5368 (3)	0.25150 (12)	0.50690 (14)	0.0546 (6)
C23	0.7679 (2)	0.45541 (12)	0.55578 (13)	0.0443 (6)
C24	0.8252 (3)	0.52589 (12)	0.56696 (14)	0.0512 (6)
C25	0.8025 (3)	0.57936 (12)	0.51301 (14)	0.0507 (6)
C26	0.7228 (2)	0.56158 (11)	0.44731 (13)	0.0424 (6)
N31	−0.09225 (19)	0.22791 (9)	0.41265 (10)	0.0406 (4)
C32	0.0442 (2)	0.19013 (11)	0.41047 (12)	0.0408 (5)
C33	0.1785 (2)	0.21210 (10)	0.37276 (11)	0.0339 (5)
C34	0.1738 (2)	0.27779 (10)	0.33334 (11)	0.0296 (5)
C35	0.0339 (2)	0.31774 (10)	0.33493 (11)	0.0335 (5)
C36	−0.0937 (2)	0.29143 (11)	0.37458 (12)	0.0390 (5)
C37	0.3104 (2)	0.30835 (10)	0.28998 (11)	0.0315 (5)
O3	0.31086 (15)	0.37316 (7)	0.27039 (8)	0.0386 (4)
N37	0.42922 (18)	0.26125 (8)	0.27497 (9)	0.0349 (4)
N47	0.56225 (19)	0.28542 (9)	0.23692 (9)	0.0360 (4)
C47	0.6705 (2)	0.23622 (11)	0.22917 (12)	0.0366 (5)
C41	0.8199 (2)	0.25275 (11)	0.19229 (12)	0.0368 (5)
C42	0.9413 (2)	0.19967 (11)	0.19138 (12)	0.0388 (5)
O42	0.91086 (16)	0.13473 (7)	0.22608 (9)	0.0441 (4)
C421	1.0376 (2)	0.08101 (11)	0.22868 (14)	0.0459 (6)
C422	0.9849 (3)	0.01803 (12)	0.27611 (14)	0.0527 (6)
C43	1.0867 (2)	0.21637 (12)	0.15773 (13)	0.0452 (6)
C44	1.1110 (3)	0.28414 (13)	0.12689 (13)	0.0493 (6)
C45	0.9937 (3)	0.33680 (13)	0.12764 (12)	0.0476 (6)
C46	0.8488 (2)	0.32095 (12)	0.15984 (12)	0.0418 (5)
H12	0.3309	0.3773	0.0125	0.053*
H13	0.4653	0.4091	0.1223	0.045*
H15	0.3039	0.6161	0.0923	0.052*
H16	0.1659	0.5757	−0.0119	0.060*
H17	0.4585	0.4540	0.2426	0.044*
H27	0.5348	0.4268	0.3567	0.044*
H22D	0.5897	0.3354	0.5799	0.055*
H22E	0.7451	0.3017	0.5413	0.055*
H22A	0.5792	0.2332	0.4597	0.082*
H22B	0.4252	0.2661	0.4994	0.082*
H22C	0.5433	0.2128	0.5448	0.082*
H23	0.7843	0.4190	0.5931	0.053*
H24	0.8808	0.5376	0.6122	0.061*
H25	0.8413	0.6277	0.5211	0.061*
H26	0.7063	0.5985	0.4105	0.051*
H32	0.0492	0.1449	0.4368	0.049*
H33	0.2723	0.1829	0.3737	0.041*
H35	0.0257	0.3630	0.3089	0.040*
H36	−0.1885	0.3200	0.3750	0.047*
H37	0.4231	0.2142	0.2852	0.042*
H47	0.6527	0.1882	0.2478	0.044*
H42D	1.1360	0.1031	0.2504	0.055*
H42E	1.0609	0.0637	0.1775	0.055*
H42A	0.8850	−0.0021	0.2555	0.079*
H42B	0.9678	0.0351	0.3273	0.079*
H42C	1.0673	−0.0201	0.2765	0.079*
H43	1.1689	0.1805	0.1563	0.054*
H44	1.2105	0.2949	0.1046	0.059*
H45	1.0120	0.3837	0.1062	0.057*
H46	0.7674	0.3572	0.1599	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0423 (11)	0.0586 (13)	0.0431 (12)	0.0058 (9)	0.0050 (9)	0.0051 (10)
C12	0.0447 (12)	0.0426 (13)	0.0441 (15)	0.0035 (11)	0.0019 (11)	−0.0020 (11)
C13	0.0366 (11)	0.0317 (11)	0.0437 (15)	0.0032 (9)	0.0006 (10)	0.0013 (10)
C14	0.0298 (10)	0.0311 (11)	0.0385 (13)	0.0007 (9)	0.0104 (9)	0.0061 (10)
C15	0.0471 (13)	0.0372 (12)	0.0467 (15)	0.0069 (10)	0.0093 (11)	0.0089 (11)
C16	0.0468 (13)	0.0563 (15)	0.0467 (16)	0.0150 (12)	0.0066 (12)	0.0174 (13)
C17	0.0338 (11)	0.0285 (11)	0.0409 (14)	0.0000 (9)	0.0103 (9)	0.0014 (10)
O1	0.0522 (9)	0.0263 (8)	0.0555 (11)	−0.0073 (7)	0.0095 (7)	0.0007 (7)
N17	0.0424 (10)	0.0276 (9)	0.0389 (11)	−0.0091 (7)	0.0008 (8)	0.0028 (8)
N27	0.0399 (10)	0.0385 (10)	0.0364 (11)	−0.0071 (8)	0.0036 (8)	−0.0018 (9)
C27	0.0336 (11)	0.0329 (11)	0.0448 (14)	−0.0029 (9)	0.0042 (10)	0.0024 (10)
C21	0.0322 (11)	0.0338 (12)	0.0413 (14)	−0.0001 (9)	0.0067 (9)	−0.0032 (10)
C22	0.0341 (11)	0.0328 (12)	0.0433 (14)	−0.0014 (9)	0.0038 (10)	−0.0037 (10)
O22	0.0461 (8)	0.0340 (8)	0.0419 (9)	−0.0028 (6)	−0.0015 (7)	0.0026 (7)
C221	0.0502 (13)	0.0396 (12)	0.0469 (15)	−0.0009 (11)	−0.0002 (11)	0.0094 (11)
C222	0.0564 (14)	0.0427 (13)	0.0646 (17)	−0.0060 (12)	−0.0034 (12)	0.0127 (12)
C23	0.0487 (13)	0.0436 (13)	0.0404 (15)	0.0035 (11)	−0.0021 (11)	0.0001 (11)
C24	0.0612 (15)	0.0464 (14)	0.0458 (16)	−0.0036 (12)	−0.0063 (12)	−0.0057 (12)
C25	0.0624 (15)	0.0415 (13)	0.0483 (16)	−0.0092 (11)	0.0028 (12)	−0.0087 (12)
C26	0.0480 (13)	0.0383 (13)	0.0412 (15)	−0.0058 (10)	0.0072 (11)	−0.0017 (10)
N31	0.0389 (10)	0.0396 (10)	0.0434 (12)	−0.0008 (8)	0.0053 (8)	0.0001 (9)
C32	0.0470 (13)	0.0343 (12)	0.0411 (14)	−0.0035 (10)	0.0035 (10)	0.0062 (10)
C33	0.0338 (11)	0.0287 (11)	0.0392 (13)	0.0015 (9)	0.0018 (9)	0.0000 (9)
C34	0.0324 (11)	0.0254 (10)	0.0310 (12)	−0.0031 (8)	−0.0029 (9)	−0.0043 (9)
C35	0.0386 (11)	0.0266 (10)	0.0352 (13)	0.0007 (9)	−0.0035 (9)	−0.0021 (9)
C36	0.0351 (11)	0.0399 (12)	0.0420 (14)	0.0011 (10)	−0.0014 (10)	−0.0090 (10)
C37	0.0344 (11)	0.0273 (11)	0.0327 (13)	−0.0021 (9)	−0.0043 (9)	−0.0008 (9)
O3	0.0402 (8)	0.0272 (8)	0.0486 (10)	−0.0036 (6)	0.0006 (7)	0.0047 (7)
N37	0.0331 (9)	0.0273 (9)	0.0444 (11)	−0.0029 (7)	0.0046 (8)	0.0043 (8)
N47	0.0318 (9)	0.0379 (10)	0.0382 (11)	−0.0039 (8)	0.0020 (8)	0.0027 (8)
C47	0.0370 (11)	0.0371 (12)	0.0356 (13)	−0.0025 (9)	−0.0028 (9)	0.0008 (10)
C41	0.0321 (11)	0.0460 (13)	0.0322 (13)	−0.0040 (10)	−0.0026 (9)	−0.0056 (10)
C42	0.0409 (12)	0.0377 (12)	0.0377 (13)	−0.0052 (10)	0.0010 (10)	−0.0092 (10)
O42	0.0363 (8)	0.0393 (8)	0.0570 (11)	0.0014 (6)	0.0084 (7)	−0.0062 (7)
C421	0.0363 (12)	0.0416 (13)	0.0600 (17)	0.0022 (10)	0.0081 (11)	−0.0143 (12)
C422	0.0486 (14)	0.0431 (13)	0.0668 (18)	0.0032 (11)	0.0098 (12)	−0.0087 (12)
C43	0.0355 (12)	0.0500 (14)	0.0504 (16)	−0.0031 (10)	0.0060 (10)	−0.0162 (12)
C44	0.0435 (13)	0.0609 (16)	0.0437 (15)	−0.0107 (12)	0.0108 (11)	−0.0068 (12)
C45	0.0447 (13)	0.0562 (15)	0.0419 (14)	−0.0108 (12)	0.0009 (11)	0.0058 (12)
C46	0.0369 (12)	0.0511 (14)	0.0374 (13)	−0.0011 (10)	−0.0005 (10)	0.0021 (11)

Geometric parameters (Å, º)

N11—C12	1.326 (3)	N31—C32	1.336 (2)
N11—C16	1.337 (3)	N31—C36	1.344 (3)
C12—C13	1.391 (3)	C32—C33	1.381 (3)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.382 (3)	C33—C34	1.390 (3)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.385 (3)	C34—C35	1.381 (3)
C14—C17	1.500 (3)	C34—C37	1.500 (3)
C15—C16	1.373 (3)	C35—C36	1.379 (3)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O1	1.232 (2)	C37—O3	1.233 (2)
C17—N17	1.344 (3)	C37—N37	1.345 (2)
N17—N27	1.387 (2)	N37—N47	1.387 (2)
N17—H17	0.8799	N37—H37	0.88
N27—C27	1.286 (3)	N47—C47	1.285 (2)
C27—C21	1.454 (3)	C47—C41	1.456 (3)
C27—H27	0.95	C47—H47	0.95
C21—C26	1.394 (3)	C41—C46	1.396 (3)
C21—C22	1.402 (3)	C41—C42	1.405 (3)
C22—O22	1.369 (2)	C42—O42	1.363 (2)
C22—C23	1.385 (3)	C42—C43	1.401 (3)
O22—C221	1.439 (2)	O42—C421	1.445 (2)
C221—C222	1.491 (3)	C421—C422	1.499 (3)
C221—H22D	0.99	C421—H42D	0.99
C221—H22E	0.99	C421—H42E	0.99
C222—H22A	0.98	C422—H42A	0.98
C222—H22B	0.98	C422—H42B	0.98
C222—H22C	0.98	C422—H42C	0.98
C23—C24	1.386 (3)	C43—C44	1.370 (3)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.382 (3)	C44—C45	1.375 (3)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.380 (3)	C45—C46	1.383 (3)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C12—N11—C16	115.5 (2)	C32—N31—C36	115.51 (17)
N11—C12—C13	124.6 (2)	N31—C32—C33	124.69 (19)
N11—C12—H12	117.7	N31—C32—H32	117.7
C13—C12—H12	117.7	C33—C32—H32	117.7
C14—C13—C12	118.45 (19)	C32—C33—C34	118.78 (18)
C14—C13—H13	120.8	C32—C33—H33	120.6
C12—C13—H13	120.8	C34—C33—H33	120.6
C13—C14—C15	117.8 (2)	C35—C34—C33	117.45 (18)
C13—C14—C17	123.88 (18)	C35—C34—C37	118.01 (17)
C15—C14—C17	118.24 (18)	C33—C34—C37	124.54 (17)
C16—C15—C14	118.8 (2)	C36—C35—C34	119.53 (19)
C16—C15—H15	120.6	C36—C35—H35	120.2
C14—C15—H15	120.6	C34—C35—H35	120.2
N11—C16—C15	124.7 (2)	N31—C36—C35	124.04 (19)
N11—C16—H16	117.6	N31—C36—H36	118.0
C15—C16—H16	117.6	C35—C36—H36	118.0
O1—C17—N17	123.7 (2)	O3—C37—N37	123.37 (18)
O1—C17—C14	120.63 (19)	O3—C37—C34	120.59 (17)
N17—C17—C14	115.72 (17)	N37—C37—C34	116.04 (16)
C17—N17—N27	118.79 (16)	C37—N37—N47	119.86 (15)
C17—N17—H17	120.6	C37—N37—H37	122.4
N27—N17—H17	120.1	N47—N37—H37	117.5
C27—N27—N17	115.17 (17)	C47—N47—N37	113.90 (16)
N27—C27—C21	119.71 (19)	N47—C47—C41	121.19 (19)
N27—C27—H27	120.1	N47—C47—H47	119.4
C21—C27—H27	120.1	C41—C47—H47	119.4
C26—C21—C22	117.8 (2)	C46—C41—C42	118.64 (19)
C26—C21—C27	121.0 (2)	C46—C41—C47	121.94 (18)
C22—C21—C27	121.20 (18)	C42—C41—C47	119.38 (19)
O22—C22—C23	123.8 (2)	O42—C42—C43	123.71 (19)
O22—C22—C21	115.43 (19)	O42—C42—C41	116.93 (18)
C23—C22—C21	120.77 (19)	C43—C42—C41	119.3 (2)
C22—O22—C221	117.74 (16)	C42—O42—C421	117.44 (16)
O22—C221—C222	107.66 (18)	O42—C421—C422	108.32 (17)
O22—C221—H22D	110.2	O42—C421—H42D	110.0
C222—C221—H22D	110.2	C422—C421—H42D	110.0
O22—C221—H22E	110.2	O42—C421—H42E	110.0
C222—C221—H22E	110.2	C422—C421—H42E	110.0
H22D—C221—H22E	108.5	H42D—C421—H42E	108.4
C221—C222—H22A	109.5	C421—C422—H42A	109.5
C221—C222—H22B	109.5	C421—C422—H42B	109.5
H22A—C222—H22B	109.5	H42A—C422—H42B	109.5
C221—C222—H22C	109.5	C421—C422—H42C	109.5
H22A—C222—H22C	109.5	H42A—C422—H42C	109.5
H22B—C222—H22C	109.5	H42B—C422—H42C	109.5
C22—C23—C24	119.7 (2)	C44—C43—C42	120.3 (2)
C22—C23—H23	120.2	C44—C43—H43	119.8
C24—C23—H23	120.2	C42—C43—H43	119.8
C25—C24—C23	120.7 (2)	C43—C44—C45	121.0 (2)
C25—C24—H24	119.6	C43—C44—H44	119.5
C23—C24—H24	119.6	C45—C44—H44	119.5
C26—C25—C24	119.1 (2)	C44—C45—C46	119.4 (2)
C26—C25—H25	120.4	C44—C45—H45	120.3
C24—C25—H25	120.4	C46—C45—H45	120.3
C25—C26—C21	121.9 (2)	C45—C46—C41	121.3 (2)
C25—C26—H26	119.1	C45—C46—H46	119.4
C21—C26—H26	119.1	C41—C46—H46	119.4
C16—N11—C12—C13	1.4 (3)	C36—N31—C32—C33	0.1 (3)
N11—C12—C13—C14	−2.0 (3)	N31—C32—C33—C34	−0.5 (3)
C12—C13—C14—C15	0.7 (3)	C32—C33—C34—C35	0.5 (3)
C12—C13—C14—C17	−177.24 (18)	C32—C33—C34—C37	179.98 (18)
C13—C14—C15—C16	1.0 (3)	C33—C34—C35—C36	−0.2 (3)
C17—C14—C15—C16	179.04 (19)	C37—C34—C35—C36	−179.67 (17)
C12—N11—C16—C15	0.5 (3)	C32—N31—C36—C35	0.3 (3)
C14—C15—C16—N11	−1.7 (3)	C34—C35—C36—N31	−0.3 (3)
C13—C14—C17—O1	147.0 (2)	C35—C34—C37—O3	15.4 (3)
C15—C14—C17—O1	−30.9 (3)	C33—C34—C37—O3	−164.00 (18)
C13—C14—C17—N17	−33.7 (3)	C35—C34—C37—N37	−164.97 (17)
C15—C14—C17—N17	148.42 (18)	C33—C34—C37—N37	15.6 (3)
O1—C17—N17—N27	0.5 (3)	O3—C37—N37—N47	1.4 (3)
C14—C17—N17—N27	−178.80 (15)	C34—C37—N37—N47	−178.23 (15)
C17—N17—N27—C27	174.10 (17)	C37—N37—N47—C47	176.85 (18)
N17—N27—C27—C21	−179.97 (16)	N37—N47—C47—C41	−178.38 (16)
N27—C27—C21—C26	8.8 (3)	N47—C47—C41—C46	−3.9 (3)
N27—C27—C21—C22	−171.40 (19)	N47—C47—C41—C42	173.85 (19)
C26—C21—C22—O22	177.04 (17)	C46—C41—C42—O42	177.60 (17)
C27—C21—C22—O22	−2.7 (3)	C47—C41—C42—O42	−0.2 (3)
C26—C21—C22—C23	−2.8 (3)	C46—C41—C42—C43	−0.4 (3)
C27—C21—C22—C23	177.38 (19)	C47—C41—C42—C43	−178.21 (18)
C23—C22—O22—C221	3.1 (3)	C43—C42—O42—C421	0.8 (3)
C21—C22—O22—C221	−176.78 (17)	C41—C42—O42—C421	−177.06 (18)
C22—O22—C221—C222	173.11 (17)	C42—O42—C421—C422	173.93 (17)
O22—C22—C23—C24	−177.98 (19)	O42—C42—C43—C44	−177.0 (2)
C21—C22—C23—C24	1.9 (3)	C41—C42—C43—C44	0.8 (3)
C22—C23—C24—C25	−0.2 (3)	C42—C43—C44—C45	−0.6 (3)
C23—C24—C25—C26	−0.5 (4)	C43—C44—C45—C46	−0.2 (4)
C24—C25—C26—C21	−0.6 (3)	C44—C45—C46—C41	0.7 (3)
C22—C21—C26—C25	2.2 (3)	C42—C41—C46—C45	−0.4 (3)
C27—C21—C26—C25	−178.03 (19)	C47—C41—C46—C45	177.40 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O3	0.88	1.99	2.836 (2)	160
N37—H37···O1^i	0.88	2.01	2.879 (2)	168
C27—H27···O3	0.95	2.60	3.352 (2)	136
C33—H33···O1^i	0.95	2.38	3.238 (2)	150
C47—H47···O1^i	0.95	2.47	3.287 (2)	145

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(XV) N-isonicotinoyl 3-ethoxybenzaldehydehydrazone

Crystal data

C15H15N3O2	F(000) = 568
Mr = 269.30	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3089 reflections
a = 24.2060 (17) Å	θ = 3.8–27.9°
b = 5.5637 (4) Å	µ = 0.09 mm^−1
c = 9.9571 (4) Å	T = 120 K
β = 94.965 (4)°	Block, colourless
V = 1335.94 (14) Å^3	0.10 × 0.04 × 0.03 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	3089 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
Detector resolution: 9.091 pixels mm^-1	θmax = 27.9°, θmin = 3.8°
ϕ & ω scans	h = −31→31
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −7→7
Tmin = 0.985, Tmax = 0.997	l = −12→12
17209 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.221	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1145P)^2 + 0.807P] where P = (Fo^2 + 2Fc^2)/3
3089 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.46930 (10)	1.2555 (4)	0.5871 (2)	0.0316 (5)
C12	0.46048 (11)	1.0481 (5)	0.6480 (2)	0.0293 (6)
C13	0.41829 (11)	0.8892 (5)	0.6054 (2)	0.0279 (6)
C14	0.38363 (10)	0.9450 (5)	0.4911 (2)	0.0258 (6)
C15	0.39299 (11)	1.1596 (5)	0.4255 (3)	0.0281 (6)
C16	0.43558 (12)	1.3083 (5)	0.4780 (3)	0.0312 (6)
C17	0.33847 (11)	0.7834 (5)	0.4321 (2)	0.0261 (6)
O1	0.32397 (8)	0.7854 (4)	0.31090 (17)	0.0336 (5)
N17	0.31707 (9)	0.6371 (4)	0.5221 (2)	0.0280 (5)
N27	0.27501 (9)	0.4788 (4)	0.4795 (2)	0.0272 (5)
C27	0.26185 (11)	0.3332 (5)	0.5710 (3)	0.0279 (6)
C21	0.21697 (11)	0.1589 (5)	0.5475 (2)	0.0261 (6)
C22	0.17571 (11)	0.1870 (5)	0.4406 (2)	0.0271 (6)
C23	0.13304 (10)	0.0221 (5)	0.4250 (2)	0.0269 (6)
O23	0.08936 (7)	0.0337 (3)	0.32784 (17)	0.0318 (5)
C231	0.08654 (11)	0.2364 (5)	0.2386 (3)	0.0315 (6)
C232	0.03418 (12)	0.2120 (6)	0.1465 (3)	0.0386 (7)
C24	0.13114 (12)	−0.1719 (5)	0.5139 (3)	0.0325 (6)
C25	0.17197 (12)	−0.1971 (5)	0.6185 (3)	0.0321 (6)
C26	0.21436 (11)	−0.0312 (5)	0.6377 (2)	0.0285 (6)
H12	0.4844	1.0061	0.7250	0.035*
H13	0.4132	0.7448	0.6537	0.034*
H15	0.3707	1.2038	0.3462	0.034*
H16	0.4410	1.4564	0.4336	0.037*
H17	0.3298	0.6421	0.6076	0.034*
H27	0.2820	0.3387	0.6572	0.034*
H22	0.1771	0.3180	0.3798	0.032*
H23B	0.1193	0.2391	0.1854	0.038*
H23A	0.0859	0.3877	0.2908	0.038*
H23C	0.0344	0.0576	0.0992	0.046*
H23D	0.0321	0.3432	0.0806	0.046*
H23E	0.0020	0.2193	0.1998	0.046*
H24	0.1019	−0.2857	0.5023	0.039*
H25	0.1709	−0.3303	0.6779	0.039*
H26	0.2415	−0.0467	0.7120	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0315 (13)	0.0344 (13)	0.0280 (11)	−0.0030 (10)	−0.0012 (9)	−0.0044 (9)
C12	0.0275 (14)	0.0358 (15)	0.0234 (12)	0.0019 (11)	−0.0041 (10)	−0.0023 (10)
C13	0.0270 (14)	0.0283 (13)	0.0283 (13)	0.0009 (11)	0.0008 (10)	0.0002 (10)
C14	0.0203 (13)	0.0311 (14)	0.0257 (12)	0.0033 (10)	0.0001 (9)	−0.0046 (10)
C15	0.0252 (14)	0.0323 (14)	0.0259 (12)	0.0030 (11)	−0.0032 (10)	0.0004 (10)
C16	0.0335 (15)	0.0309 (14)	0.0288 (13)	0.0011 (12)	0.0006 (11)	−0.0015 (11)
C17	0.0217 (13)	0.0299 (14)	0.0261 (13)	0.0022 (11)	−0.0011 (10)	−0.0006 (10)
O1	0.0327 (11)	0.0428 (11)	0.0242 (9)	−0.0096 (9)	−0.0041 (7)	0.0007 (8)
N17	0.0227 (11)	0.0318 (12)	0.0282 (11)	−0.0026 (9)	−0.0049 (8)	−0.0017 (9)
N27	0.0212 (11)	0.0313 (12)	0.0282 (11)	−0.0033 (9)	−0.0031 (8)	−0.0053 (9)
C27	0.0221 (13)	0.0313 (14)	0.0296 (13)	0.0003 (11)	−0.0018 (10)	−0.0011 (10)
C21	0.0206 (13)	0.0271 (13)	0.0303 (13)	0.0024 (10)	0.0003 (10)	−0.0016 (10)
C22	0.0257 (14)	0.0280 (13)	0.0271 (13)	0.0008 (11)	0.0002 (10)	0.0007 (10)
C23	0.0226 (13)	0.0333 (14)	0.0242 (12)	0.0000 (11)	−0.0005 (9)	−0.0029 (10)
O23	0.0263 (10)	0.0393 (11)	0.0285 (10)	−0.0069 (8)	−0.0042 (7)	0.0004 (8)
C231	0.0255 (14)	0.0369 (15)	0.0314 (14)	0.0012 (12)	−0.0019 (10)	0.0012 (11)
C232	0.0286 (15)	0.0482 (18)	0.0375 (16)	0.0035 (13)	−0.0060 (12)	−0.0006 (13)
C24	0.0340 (16)	0.0272 (14)	0.0364 (14)	−0.0052 (12)	0.0029 (11)	−0.0023 (11)
C25	0.0329 (15)	0.0265 (13)	0.0367 (14)	0.0030 (11)	0.0015 (11)	0.0023 (11)
C26	0.0272 (14)	0.0298 (14)	0.0278 (13)	0.0032 (11)	−0.0020 (10)	0.0009 (10)

Geometric parameters (Å, º)

N11—C12	1.329 (4)	C21—C26	1.393 (4)
N11—C16	1.334 (3)	C21—C22	1.403 (3)
C12—C13	1.389 (4)	C22—C23	1.380 (4)
C12—H12	0.95	C22—H22	0.95
C13—C14	1.390 (3)	C23—O23	1.371 (3)
C13—H13	0.95	C23—C24	1.399 (4)
C14—C15	1.389 (4)	O23—C231	1.434 (3)
C14—C17	1.496 (4)	C231—C232	1.505 (4)
C15—C16	1.388 (4)	C231—H23B	0.99
C15—H15	0.95	C231—H23A	0.99
C16—H16	0.95	C232—H23C	0.98
C17—O1	1.227 (3)	C232—H23D	0.98
C17—N17	1.347 (3)	C232—H23E	0.98
N17—N27	1.385 (3)	C24—C25	1.379 (4)
N17—H17	0.88	C24—H24	0.95
N27—C27	1.280 (3)	C25—C26	1.381 (4)
C27—C21	1.460 (4)	C25—H25	0.95
C27—H27	0.95	C26—H26	0.95
C12—N11—C16	116.8 (2)	C23—C22—C21	119.2 (2)
N11—C12—C13	123.8 (2)	C23—C22—H22	120.4
N11—C12—H12	118.1	C21—C22—H22	120.4
C13—C12—H12	118.1	O23—C23—C22	124.9 (2)
C12—C13—C14	118.9 (2)	O23—C23—C24	114.7 (2)
C12—C13—H13	120.5	C22—C23—C24	120.4 (2)
C14—C13—H13	120.5	C23—O23—C231	117.8 (2)
C15—C14—C13	117.8 (2)	O23—C231—C232	107.4 (2)
C15—C14—C17	118.4 (2)	O23—C231—H23B	110.2
C13—C14—C17	123.8 (2)	C232—C231—H23B	110.2
C16—C15—C14	118.7 (2)	O23—C231—H23A	110.2
C16—C15—H15	120.6	C232—C231—H23A	110.2
C14—C15—H15	120.6	H23B—C231—H23A	108.5
N11—C16—C15	123.9 (3)	C231—C232—H23C	109.5
N11—C16—H16	118.0	C231—C232—H23D	109.5
C15—C16—H16	118.0	H23C—C232—H23D	109.5
O1—C17—N17	124.5 (2)	C231—C232—H23E	109.5
O1—C17—C14	121.2 (2)	H23C—C232—H23E	109.5
N17—C17—C14	114.3 (2)	H23D—C232—H23E	109.5
C17—N17—N27	119.7 (2)	C25—C24—C23	119.7 (3)
C17—N17—H17	120.2	C25—C24—H24	120.1
N27—N17—H17	120.2	C23—C24—H24	120.1
C27—N27—N17	113.9 (2)	C24—C25—C26	120.8 (3)
N27—C27—C21	122.2 (2)	C24—C25—H25	119.6
N27—C27—H27	118.9	C26—C25—H25	119.6
C21—C27—H27	118.9	C25—C26—C21	119.5 (2)
C26—C21—C22	120.3 (2)	C25—C26—H26	120.2
C26—C21—C27	118.4 (2)	C21—C26—H26	120.2
C22—C21—C27	121.2 (2)
C16—N11—C12—C13	−1.0 (4)	N27—C27—C21—C26	163.7 (3)
N11—C12—C13—C14	1.4 (4)	N27—C27—C21—C22	−19.4 (4)
C12—C13—C14—C15	−0.4 (4)	C26—C21—C22—C23	−0.9 (4)
C12—C13—C14—C17	177.2 (2)	C27—C21—C22—C23	−177.8 (2)
C13—C14—C15—C16	−1.0 (4)	C21—C22—C23—O23	177.7 (2)
C17—C14—C15—C16	−178.7 (2)	C21—C22—C23—C24	−0.5 (4)
C12—N11—C16—C15	−0.5 (4)	C22—C23—O23—C231	−2.4 (4)
C14—C15—C16—N11	1.5 (4)	C24—C23—O23—C231	176.0 (2)
C15—C14—C17—O1	26.8 (4)	C23—O23—C231—C232	−177.7 (2)
C13—C14—C17—O1	−150.8 (3)	O23—C23—C24—C25	−177.9 (2)
C15—C14—C17—N17	−154.6 (2)	C22—C23—C24—C25	0.5 (4)
C13—C14—C17—N17	27.8 (4)	C23—C24—C25—C26	0.9 (4)
O1—C17—N17—N27	−1.3 (4)	C24—C25—C26—C21	−2.4 (4)
C14—C17—N17—N27	−179.9 (2)	C22—C21—C26—C25	2.4 (4)
C17—N17—N27—C27	173.5 (2)	C27—C21—C26—C25	179.3 (2)
N17—N27—C27—C21	177.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O1^i	0.88	2.08	2.898 (3)	154
C12—H12···N11^ii	0.95	2.52	3.424 (3)	160

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2.