4-(N,N-Di-4-tolyl­amino)­benz­aldehyde (3-pyridyl­carbonyl)­hydrazone monohydrate

The crystal structure of the title compound, C₂₇H₂₄N₄O·H₂O, containing tri­aryl­amine and benzoic hydrazide units and water of crystallization, shows a variety of hydrogen bonds, as well as features in which the N atom in the tri­aryl­amine moiety is sp²-hybridized and the three benzene rings are twisted with respect to one another.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.138
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

4-(N,N-Di-4-tolylamino)benzaldehyde (3-pyridylcarbonyl)hydrazone monohydrate

Crystal data

C27H24N4O·H2O	F(000) = 928
Mr = 438.52	Dx = 1.237 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 998 reflections
a = 11.425 (3) Å	θ = 2.5–24.0°
b = 12.404 (4) Å	µ = 0.08 mm^−1
c = 17.374 (5) Å	T = 293 K
β = 106.951 (5)°	Prism, green-yellow
V = 2355.3 (12) Å^3	0.42 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4823 independent reflections
Radiation source: fine-focus sealed tube	3093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→9
Tmin = 0.978, Tmax = 0.984	k = −15→15
13225 measured reflections	l = −21→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.4561P] where P = (Fo^2 + 2Fc^2)/3
4823 reflections	(Δ/σ)max = 0.002
300 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.6285 (2)	0.6144 (2)	−0.00995 (12)	0.0761 (6)
N2	0.52986 (14)	0.54021 (13)	0.23010 (9)	0.0461 (4)
H2	0.5386	0.4736	0.2191	0.055*
N3	0.48156 (14)	0.56772 (13)	0.29193 (9)	0.0448 (4)
N4	0.19990 (15)	0.54972 (13)	0.56390 (10)	0.0469 (4)
O1	0.55038 (14)	0.71553 (11)	0.19883 (9)	0.0608 (4)
H2A	0.4301	0.3488	0.1414	0.091*
H2B	0.4903	0.2704	0.1962	0.091*
C1	0.5887 (2)	0.63883 (19)	0.05217 (13)	0.0595 (6)
H1	0.5389	0.6992	0.0476	0.071*
C2	0.61545 (18)	0.58157 (16)	0.12313 (11)	0.0458 (5)
C3	0.6906 (2)	0.4928 (2)	0.12981 (14)	0.0648 (6)
H3	0.7126	0.4524	0.1769	0.078*
C4	0.7323 (3)	0.4650 (2)	0.06610 (17)	0.0818 (8)
H4	0.7822	0.4050	0.0690	0.098*
C5	0.6995 (3)	0.5269 (3)	−0.00150 (17)	0.0860 (8)
H5	0.7282	0.5072	−0.0444	0.103*
C6	0.56275 (18)	0.61895 (16)	0.18759 (11)	0.0447 (5)
C7	0.43578 (17)	0.48951 (16)	0.32144 (11)	0.0453 (5)
H7	0.4394	0.4202	0.3018	0.054*
C8	0.37829 (17)	0.50592 (16)	0.38476 (11)	0.0428 (5)
C9	0.31400 (18)	0.42206 (16)	0.40672 (12)	0.0455 (5)
H9	0.3105	0.3557	0.3812	0.055*
C10	0.25516 (17)	0.43410 (16)	0.46515 (12)	0.0450 (5)
H10	0.2122	0.3765	0.4779	0.054*
C11	0.25974 (16)	0.53213 (15)	0.50524 (11)	0.0410 (4)
C12	0.32548 (19)	0.61639 (17)	0.48372 (12)	0.0508 (5)
H12	0.3306	0.6824	0.5099	0.061*
C13	0.38248 (19)	0.60386 (17)	0.42491 (12)	0.0517 (5)
H13	0.4246	0.6617	0.4116	0.062*
C14	0.17737 (17)	0.65909 (15)	0.58368 (11)	0.0416 (4)
C15	0.0855 (2)	0.71895 (17)	0.53250 (12)	0.0545 (5)
H15	0.0387	0.6897	0.4840	0.065*
C16	0.0632 (2)	0.82239 (19)	0.55358 (14)	0.0630 (6)
H16	0.0006	0.8621	0.5190	0.076*
C17	0.1317 (2)	0.86850 (17)	0.62479 (14)	0.0570 (6)
C18	0.2232 (2)	0.80729 (19)	0.67450 (14)	0.0599 (6)
H18	0.2707	0.8365	0.7228	0.072*
C19	0.24604 (18)	0.70380 (17)	0.65447 (13)	0.0521 (5)
H19	0.3084	0.6640	0.6892	0.063*
C20	0.1051 (3)	0.9814 (2)	0.64862 (18)	0.0932 (10)
H20A	0.0921	1.0286	0.6031	0.140*
H20B	0.1734	1.0069	0.6914	0.140*
H20C	0.0332	0.9803	0.6665	0.140*
C21	0.15786 (17)	0.46710 (15)	0.60601 (11)	0.0406 (4)
C22	0.05155 (18)	0.48316 (16)	0.62805 (12)	0.0477 (5)
H22	0.0076	0.5468	0.6137	0.057*
C23	0.01083 (19)	0.40604 (18)	0.67082 (12)	0.0535 (5)
H23	−0.0607	0.4187	0.6847	0.064*
C24	0.0727 (2)	0.31014 (17)	0.69393 (12)	0.0520 (5)
C25	0.17798 (19)	0.29433 (17)	0.67122 (12)	0.0517 (5)
H25	0.2210	0.2301	0.6850	0.062*
C26	0.22097 (17)	0.37114 (16)	0.62879 (12)	0.0474 (5)
H26	0.2928	0.3585	0.6153	0.057*
C27	0.0287 (3)	0.2261 (2)	0.74227 (18)	0.0862 (9)
H27A	0.0268	0.2567	0.7926	0.129*
H27B	0.0835	0.1656	0.7521	0.129*
H27C	−0.0520	0.2027	0.7127	0.129*
O2	0.49979 (17)	0.32773 (12)	0.17148 (9)	0.0719 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0966 (16)	0.0892 (17)	0.0511 (11)	−0.0023 (13)	0.0354 (11)	0.0032 (11)
N2	0.0609 (10)	0.0393 (9)	0.0456 (9)	0.0040 (8)	0.0275 (8)	−0.0021 (7)
N3	0.0532 (10)	0.0437 (10)	0.0430 (9)	0.0041 (7)	0.0224 (8)	−0.0016 (7)
N4	0.0573 (10)	0.0365 (9)	0.0570 (10)	0.0013 (7)	0.0327 (8)	−0.0024 (7)
O1	0.0849 (11)	0.0413 (9)	0.0651 (9)	0.0014 (7)	0.0360 (8)	−0.0012 (7)
C1	0.0699 (15)	0.0610 (15)	0.0495 (12)	−0.0028 (11)	0.0203 (11)	0.0030 (10)
C2	0.0485 (11)	0.0465 (12)	0.0449 (11)	−0.0054 (9)	0.0175 (9)	−0.0012 (9)
C3	0.0701 (15)	0.0687 (16)	0.0653 (14)	0.0125 (12)	0.0349 (12)	0.0098 (12)
C4	0.0888 (19)	0.085 (2)	0.0904 (19)	0.0213 (15)	0.0557 (16)	0.0025 (16)
C5	0.101 (2)	0.107 (2)	0.0695 (17)	−0.0024 (18)	0.0565 (16)	−0.0085 (16)
C6	0.0505 (11)	0.0408 (12)	0.0447 (11)	−0.0003 (9)	0.0168 (9)	0.0001 (9)
C7	0.0524 (12)	0.0409 (11)	0.0465 (11)	0.0049 (9)	0.0205 (9)	0.0002 (9)
C8	0.0465 (11)	0.0427 (11)	0.0430 (10)	0.0042 (9)	0.0187 (9)	0.0010 (8)
C9	0.0515 (11)	0.0383 (11)	0.0513 (11)	0.0044 (9)	0.0220 (9)	−0.0023 (9)
C10	0.0483 (11)	0.0379 (11)	0.0533 (11)	−0.0008 (8)	0.0218 (9)	0.0020 (9)
C11	0.0409 (10)	0.0399 (11)	0.0463 (11)	0.0024 (8)	0.0189 (9)	0.0011 (8)
C12	0.0629 (13)	0.0412 (12)	0.0568 (12)	−0.0062 (9)	0.0310 (11)	−0.0088 (9)
C13	0.0619 (13)	0.0435 (12)	0.0592 (12)	−0.0085 (10)	0.0324 (11)	−0.0017 (10)
C14	0.0450 (11)	0.0415 (11)	0.0450 (11)	−0.0005 (8)	0.0234 (9)	−0.0018 (8)
C15	0.0656 (14)	0.0520 (13)	0.0440 (11)	0.0053 (11)	0.0132 (10)	−0.0024 (9)
C16	0.0798 (16)	0.0537 (14)	0.0590 (14)	0.0214 (12)	0.0255 (12)	0.0111 (11)
C17	0.0843 (16)	0.0406 (12)	0.0616 (14)	0.0001 (11)	0.0455 (13)	−0.0003 (10)
C18	0.0661 (14)	0.0582 (14)	0.0589 (13)	−0.0167 (12)	0.0235 (11)	−0.0177 (11)
C19	0.0456 (11)	0.0536 (13)	0.0552 (12)	0.0001 (9)	0.0116 (10)	−0.0023 (10)
C20	0.155 (3)	0.0478 (15)	0.100 (2)	0.0112 (16)	0.073 (2)	−0.0044 (14)
C21	0.0435 (10)	0.0394 (11)	0.0415 (10)	−0.0034 (8)	0.0165 (8)	−0.0033 (8)
C22	0.0507 (12)	0.0436 (11)	0.0543 (12)	0.0033 (9)	0.0242 (10)	−0.0031 (9)
C23	0.0567 (13)	0.0558 (13)	0.0606 (13)	−0.0025 (10)	0.0369 (11)	−0.0071 (11)
C24	0.0682 (14)	0.0478 (12)	0.0492 (11)	−0.0063 (10)	0.0314 (11)	−0.0035 (9)
C25	0.0588 (13)	0.0443 (12)	0.0539 (12)	0.0041 (10)	0.0193 (10)	0.0046 (9)
C26	0.0416 (11)	0.0514 (12)	0.0534 (12)	0.0046 (9)	0.0203 (9)	0.0021 (9)
C27	0.120 (2)	0.0624 (17)	0.102 (2)	0.0002 (15)	0.0743 (19)	0.0110 (14)
O2	0.1127 (13)	0.0446 (9)	0.0583 (9)	−0.0071 (9)	0.0248 (9)	0.0048 (7)

Geometric parameters (Å, º)

N1—C1	1.323 (3)	C14—C19	1.369 (3)
N1—C5	1.337 (4)	C14—C15	1.378 (3)
N2—C6	1.343 (2)	C15—C16	1.378 (3)
N2—N3	1.386 (2)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.380 (3)
N3—C7	1.278 (2)	C16—H16	0.9300
N4—C11	1.400 (2)	C17—C18	1.374 (3)
N4—C21	1.422 (2)	C17—C20	1.516 (3)
N4—C14	1.441 (2)	C18—C19	1.375 (3)
O1—C6	1.229 (2)	C18—H18	0.9300
C1—C2	1.378 (3)	C19—H19	0.9300
C1—H1	0.9300	C20—H20A	0.9600
C2—C3	1.380 (3)	C20—H20B	0.9600
C2—C6	1.492 (3)	C20—H20C	0.9600
C3—C4	1.371 (3)	C21—C26	1.388 (3)
C3—H3	0.9300	C21—C22	1.390 (3)
C4—C5	1.361 (4)	C22—C23	1.373 (3)
C4—H4	0.9300	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.382 (3)
C7—C8	1.451 (3)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.384 (3)
C8—C9	1.389 (3)	C24—C27	1.514 (3)
C8—C13	1.395 (3)	C25—C26	1.380 (3)
C9—C10	1.379 (3)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.395 (3)	C27—H27A	0.9600
C10—H10	0.9300	C27—H27B	0.9600
C11—C12	1.400 (3)	C27—H27C	0.9600
C12—C13	1.371 (3)	O2—H2A	0.8561
C12—H12	0.9300	O2—H2B	0.8539
C13—H13	0.9300
C1—N1—C5	116.0 (2)	C19—C14—N4	120.02 (18)
C6—N2—N3	119.07 (16)	C15—C14—N4	120.58 (17)
C6—N2—H2	120.5	C16—C15—C14	119.7 (2)
N3—N2—H2	120.5	C16—C15—H15	120.2
C7—N3—N2	115.21 (16)	C14—C15—H15	120.2
C11—N4—C21	124.90 (15)	C15—C16—C17	121.6 (2)
C11—N4—C14	118.64 (15)	C15—C16—H16	119.2
C21—N4—C14	116.45 (15)	C17—C16—H16	119.2
N1—C1—C2	125.0 (2)	C18—C17—C16	117.6 (2)
N1—C1—H1	117.5	C18—C17—C20	121.0 (2)
C2—C1—H1	117.5	C16—C17—C20	121.4 (2)
C1—C2—C3	117.2 (2)	C17—C18—C19	121.5 (2)
C1—C2—C6	118.62 (19)	C17—C18—H18	119.2
C3—C2—C6	124.21 (18)	C19—C18—H18	119.2
C4—C3—C2	119.2 (2)	C14—C19—C18	120.3 (2)
C4—C3—H3	120.4	C14—C19—H19	119.9
C2—C3—H3	120.4	C18—C19—H19	119.9
C5—C4—C3	118.8 (3)	C17—C20—H20A	109.5
C5—C4—H4	120.6	C17—C20—H20B	109.5
C3—C4—H4	120.6	H20A—C20—H20B	109.5
N1—C5—C4	123.9 (2)	C17—C20—H20C	109.5
N1—C5—H5	118.0	H20A—C20—H20C	109.5
C4—C5—H5	118.0	H20B—C20—H20C	109.5
O1—C6—N2	123.94 (18)	C26—C21—C22	117.85 (18)
O1—C6—C2	120.85 (18)	C26—C21—N4	122.65 (17)
N2—C6—C2	115.21 (17)	C22—C21—N4	119.47 (17)
N3—C7—C8	121.76 (18)	C23—C22—C21	120.69 (19)
N3—C7—H7	119.1	C23—C22—H22	119.7
C8—C7—H7	119.1	C21—C22—H22	119.7
C9—C8—C13	117.29 (17)	C22—C23—C24	122.09 (19)
C9—C8—C7	119.71 (18)	C22—C23—H23	119.0
C13—C8—C7	122.99 (18)	C24—C23—H23	119.0
C10—C9—C8	122.08 (18)	C23—C24—C25	116.91 (19)
C10—C9—H9	119.0	C23—C24—C27	121.9 (2)
C8—C9—H9	119.0	C25—C24—C27	121.1 (2)
C9—C10—C11	120.44 (18)	C26—C25—C24	121.91 (19)
C9—C10—H10	119.8	C26—C25—H25	119.0
C11—C10—H10	119.8	C24—C25—H25	119.0
C10—C11—C12	117.55 (17)	C25—C26—C21	120.55 (18)
C10—C11—N4	122.98 (17)	C25—C26—H26	119.7
C12—C11—N4	119.46 (17)	C21—C26—H26	119.7
C13—C12—C11	121.51 (18)	C24—C27—H27A	109.5
C13—C12—H12	119.2	C24—C27—H27B	109.5
C11—C12—H12	119.2	H27A—C27—H27B	109.5
C12—C13—C8	121.13 (19)	C24—C27—H27C	109.5
C12—C13—H13	119.4	H27A—C27—H27C	109.5
C8—C13—H13	119.4	H27B—C27—H27C	109.5
C19—C14—C15	119.39 (19)	H2A—O2—H2B	109.3
C6—N2—N3—C7	169.97 (18)	C9—C8—C13—C12	0.1 (3)
C5—N1—C1—C2	0.3 (4)	C7—C8—C13—C12	179.13 (19)
N1—C1—C2—C3	0.8 (3)	C11—N4—C14—C19	−105.6 (2)
N1—C1—C2—C6	−179.6 (2)	C21—N4—C14—C19	74.9 (2)
C1—C2—C3—C4	−1.3 (3)	C11—N4—C14—C15	75.6 (2)
C6—C2—C3—C4	179.1 (2)	C21—N4—C14—C15	−103.9 (2)
C2—C3—C4—C5	0.9 (4)	C19—C14—C15—C16	−0.6 (3)
C1—N1—C5—C4	−0.7 (4)	N4—C14—C15—C16	178.22 (19)
C3—C4—C5—N1	0.2 (5)	C14—C15—C16—C17	0.6 (4)
N3—N2—C6—O1	−1.6 (3)	C15—C16—C17—C18	−0.2 (3)
N3—N2—C6—C2	179.14 (15)	C15—C16—C17—C20	−178.6 (2)
C1—C2—C6—O1	−35.7 (3)	C16—C17—C18—C19	−0.1 (3)
C3—C2—C6—O1	143.9 (2)	C20—C17—C18—C19	178.3 (2)
C1—C2—C6—N2	143.5 (2)	C15—C14—C19—C18	0.3 (3)
C3—C2—C6—N2	−36.8 (3)	N4—C14—C19—C18	−178.55 (19)
N2—N3—C7—C8	−178.03 (16)	C17—C18—C19—C14	0.1 (3)
N3—C7—C8—C9	170.50 (19)	C11—N4—C21—C26	36.1 (3)
N3—C7—C8—C13	−8.5 (3)	C14—N4—C21—C26	−144.41 (19)
C13—C8—C9—C10	0.6 (3)	C11—N4—C21—C22	−146.10 (19)
C7—C8—C9—C10	−178.41 (18)	C14—N4—C21—C22	33.4 (2)
C8—C9—C10—C11	−0.8 (3)	C26—C21—C22—C23	−0.1 (3)
C9—C10—C11—C12	0.1 (3)	N4—C21—C22—C23	−178.07 (18)
C9—C10—C11—N4	178.73 (17)	C21—C22—C23—C24	0.2 (3)
C21—N4—C11—C10	18.6 (3)	C22—C23—C24—C25	−0.7 (3)
C14—N4—C11—C10	−160.90 (18)	C22—C23—C24—C27	179.0 (2)
C21—N4—C11—C12	−162.82 (18)	C23—C24—C25—C26	1.2 (3)
C14—N4—C11—C12	17.7 (3)	C27—C24—C25—C26	−178.5 (2)
C10—C11—C12—C13	0.6 (3)	C24—C25—C26—C21	−1.2 (3)
N4—C11—C12—C13	−178.03 (19)	C22—C21—C26—C25	0.6 (3)
C11—C12—C13—C8	−0.7 (3)	N4—C21—C26—C25	178.50 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.99	2.810 (2)	160
O2—H2A···N1^i	0.86	2.23	2.853 (3)	129
O2—H2B···O1^ii	0.85	2.12	2.845 (2)	142
O2—H2B···N3^ii	0.85	2.54	3.282 (2)	147

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