N′′-N′′′-Bis(di-2-pyridylmethyl­ene)carbonic dihydrazide

The title compound {alternative name: 1,3-bis­(di-2-pyridyl­methyl­ene)amino]urea}, C₂₃H₁₈N₈O, adopts an EE configuration about the hydrazine bonds and exists in the ketone form. Intra­molecular N—H...N hydrogen bonds are observed. Mol­ecules translated by one unit cell along the a-axis direction are linked by C—H...O hydrogen-bonding inter­actions, forming a chain. In addition, C—H...π and π–π inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.116
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

N''-N'''-Bis(di-2-pyridylmethylene)carbonic dihydrazide

Crystal data

C23H18N8O	Z = 2
Mr = 422.45	F(000) = 440
Triclinic, P1	Dx = 1.378 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0963 (2) Å	Cell parameters from 4652 reflections
b = 9.1215 (2) Å	θ = 2.5–27.5°
c = 13.6215 (3) Å	µ = 0.09 mm^−1
α = 71.136 (1)°	T = 297 K
β = 86.899 (1)°	Block, colourless
γ = 72.431 (1)°	0.31 × 0.26 × 0.19 mm
V = 1018.42 (4) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4652 independent reflections
Radiation source: fine-focus sealed tube	3235 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.972, Tmax = 0.983	l = −16→17
17391 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.1398P] where P = (Fo^2 + 2Fc^2)/3
4652 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.21 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
O1	0.45455 (13)	0.69567 (18)	−0.02572 (10)	0.0691 (4)
N1	0.95454 (14)	0.73741 (16)	0.07445 (10)	0.0441 (3)
N2	0.71948 (16)	0.78608 (18)	0.33244 (10)	0.0537 (4)
N3	0.62048 (14)	0.77891 (16)	0.09495 (10)	0.0448 (3)
N4	0.67707 (16)	0.74394 (17)	0.00748 (10)	0.0470 (3)
H1N4	0.779 (2)	0.729 (2)	−0.0072 (14)	0.065 (5)*
N5	0.65423 (15)	0.65659 (18)	−0.12973 (11)	0.0485 (3)
H1N5	0.604 (2)	0.623 (2)	−0.1661 (14)	0.059 (5)*
N6	0.79043 (13)	0.68394 (16)	−0.16076 (10)	0.0428 (3)
N7	1.00664 (16)	0.78561 (19)	−0.36287 (11)	0.0567 (4)
N8	0.65389 (15)	0.56455 (17)	−0.29933 (11)	0.0496 (3)
C1	1.09884 (18)	0.7444 (2)	0.05933 (12)	0.0488 (4)
H1A	1.1598	0.6847	0.0200	0.059*
C2	1.16326 (19)	0.8338 (2)	0.09802 (13)	0.0521 (4)
H2A	1.2653	0.8327	0.0867	0.063*
C3	1.0719 (2)	0.9248 (2)	0.15389 (13)	0.0559 (4)
H3A	1.1102	0.9898	0.1794	0.067*
C4	0.92328 (19)	0.9190 (2)	0.17191 (13)	0.0507 (4)
H4A	0.8605	0.9793	0.2102	0.061*
C5	0.86782 (16)	0.82228 (17)	0.13243 (11)	0.0395 (3)
C6	0.70753 (17)	0.81308 (18)	0.15101 (11)	0.0400 (3)
C7	0.63067 (17)	0.84473 (18)	0.24471 (11)	0.0409 (3)
C8	0.6504 (2)	0.8083 (2)	0.41801 (13)	0.0590 (5)
H8A	0.7106	0.7685	0.4794	0.071*
C9	0.4966 (2)	0.8859 (2)	0.42058 (14)	0.0563 (5)
H9A	0.4537	0.8963	0.4824	0.068*
C10	0.4073 (2)	0.9480 (2)	0.33023 (14)	0.0558 (4)
H10A	0.3027	1.0030	0.3293	0.067*
C11	0.47518 (18)	0.92744 (19)	0.24047 (13)	0.0477 (4)
H11A	0.4171	0.9687	0.1781	0.057*
C12	0.58500 (18)	0.6992 (2)	−0.04615 (13)	0.0474 (4)
C13	0.85474 (16)	0.64519 (18)	−0.23973 (11)	0.0391 (3)
C14	1.00065 (16)	0.68915 (18)	−0.26613 (12)	0.0403 (3)
C15	1.1353 (2)	0.8309 (2)	−0.38515 (15)	0.0629 (5)
H15A	1.1412	0.9000	−0.4516	0.075*
C16	1.2582 (2)	0.7817 (2)	−0.31629 (15)	0.0590 (5)
H16A	1.3450	0.8160	−0.3358	0.071*
C17	1.2507 (2)	0.6808 (3)	−0.21785 (15)	0.0626 (5)
H17A	1.3328	0.6443	−0.1694	0.075*
C18	1.11901 (18)	0.6346 (2)	−0.19221 (13)	0.0516 (4)
H18A	1.1103	0.5673	−0.1257	0.062*
C19	0.80320 (17)	0.56104 (18)	−0.30157 (11)	0.0400 (3)
C20	0.6104 (2)	0.4848 (2)	−0.35373 (14)	0.0596 (5)
H20A	0.5077	0.4860	−0.3527	0.072*
C21	0.7085 (2)	0.4013 (2)	−0.41106 (14)	0.0606 (5)
H21A	0.6722	0.3499	−0.4491	0.073*
C22	0.8603 (2)	0.3951 (2)	−0.41121 (14)	0.0575 (4)
H22A	0.9296	0.3371	−0.4480	0.069*
C23	0.90954 (19)	0.47586 (19)	−0.35621 (12)	0.0471 (4)
H23A	1.0124	0.4735	−0.3556	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0413 (7)	0.1177 (11)	0.0764 (9)	−0.0358 (7)	0.0217 (6)	−0.0602 (8)
N1	0.0381 (7)	0.0559 (7)	0.0418 (7)	−0.0153 (6)	0.0080 (6)	−0.0204 (6)
N2	0.0489 (8)	0.0697 (9)	0.0369 (7)	−0.0118 (7)	0.0042 (6)	−0.0159 (6)
N3	0.0402 (7)	0.0595 (8)	0.0381 (7)	−0.0146 (6)	0.0086 (6)	−0.0216 (6)
N4	0.0356 (7)	0.0738 (9)	0.0414 (7)	−0.0195 (6)	0.0102 (6)	−0.0303 (7)
N5	0.0363 (7)	0.0746 (9)	0.0512 (8)	−0.0244 (7)	0.0118 (6)	−0.0367 (7)
N6	0.0325 (6)	0.0583 (8)	0.0433 (7)	−0.0160 (6)	0.0060 (5)	−0.0224 (6)
N7	0.0462 (8)	0.0760 (10)	0.0461 (8)	−0.0243 (7)	0.0065 (6)	−0.0126 (7)
N8	0.0395 (7)	0.0678 (9)	0.0530 (8)	−0.0208 (6)	0.0026 (6)	−0.0304 (7)
C1	0.0393 (9)	0.0624 (10)	0.0460 (9)	−0.0145 (7)	0.0099 (7)	−0.0210 (8)
C2	0.0413 (9)	0.0715 (11)	0.0467 (9)	−0.0241 (8)	0.0061 (7)	−0.0173 (8)
C3	0.0545 (10)	0.0721 (11)	0.0545 (10)	−0.0310 (9)	0.0067 (8)	−0.0277 (9)
C4	0.0507 (10)	0.0620 (10)	0.0480 (10)	−0.0198 (8)	0.0099 (8)	−0.0277 (8)
C5	0.0389 (8)	0.0470 (8)	0.0320 (7)	−0.0132 (6)	0.0058 (6)	−0.0122 (6)
C6	0.0368 (8)	0.0471 (8)	0.0360 (8)	−0.0115 (6)	0.0048 (6)	−0.0147 (6)
C7	0.0410 (8)	0.0465 (8)	0.0358 (8)	−0.0136 (6)	0.0071 (6)	−0.0146 (6)
C8	0.0672 (12)	0.0744 (12)	0.0350 (9)	−0.0226 (9)	0.0064 (8)	−0.0167 (8)
C9	0.0682 (12)	0.0663 (11)	0.0467 (10)	−0.0302 (9)	0.0256 (9)	−0.0287 (8)
C10	0.0475 (10)	0.0621 (10)	0.0618 (11)	−0.0152 (8)	0.0186 (8)	−0.0289 (9)
C11	0.0421 (9)	0.0565 (9)	0.0434 (9)	−0.0121 (7)	0.0058 (7)	−0.0176 (7)
C12	0.0366 (8)	0.0654 (10)	0.0483 (9)	−0.0172 (7)	0.0078 (7)	−0.0282 (8)
C13	0.0325 (7)	0.0492 (8)	0.0377 (8)	−0.0108 (6)	0.0032 (6)	−0.0182 (6)
C14	0.0340 (8)	0.0503 (8)	0.0418 (8)	−0.0124 (6)	0.0053 (6)	−0.0225 (7)
C15	0.0567 (11)	0.0797 (13)	0.0535 (11)	−0.0311 (10)	0.0144 (9)	−0.0152 (9)
C16	0.0455 (10)	0.0773 (12)	0.0687 (12)	−0.0316 (9)	0.0183 (9)	−0.0331 (10)
C17	0.0431 (10)	0.0897 (13)	0.0628 (12)	−0.0281 (9)	−0.0004 (8)	−0.0269 (10)
C18	0.0411 (9)	0.0683 (10)	0.0469 (9)	−0.0212 (8)	0.0008 (7)	−0.0161 (8)
C19	0.0372 (8)	0.0480 (8)	0.0368 (8)	−0.0136 (6)	0.0018 (6)	−0.0153 (6)
C20	0.0525 (10)	0.0795 (12)	0.0632 (11)	−0.0319 (9)	0.0021 (9)	−0.0331 (10)
C21	0.0740 (13)	0.0669 (11)	0.0595 (11)	−0.0333 (10)	0.0059 (9)	−0.0341 (9)
C22	0.0675 (12)	0.0585 (10)	0.0560 (11)	−0.0211 (9)	0.0108 (9)	−0.0302 (8)
C23	0.0439 (9)	0.0535 (9)	0.0463 (9)	−0.0136 (7)	0.0052 (7)	−0.0207 (7)

Geometric parameters (Å, º)

O1—C12	1.2116 (18)	C7—C11	1.382 (2)
N1—C1	1.3349 (19)	C8—C9	1.368 (2)
N1—C5	1.3434 (18)	C8—H8A	0.93
N2—C8	1.338 (2)	C9—C10	1.370 (3)
N2—C7	1.3406 (19)	C9—H9A	0.93
N3—C6	1.2945 (19)	C10—C11	1.381 (2)
N3—N4	1.3662 (17)	C10—H10A	0.93
N4—C12	1.367 (2)	C11—H11A	0.93
N4—H1N4	0.916 (19)	C13—C19	1.482 (2)
N5—N6	1.3556 (17)	C13—C14	1.493 (2)
N5—C12	1.3799 (19)	C14—C18	1.375 (2)
N5—H1N5	0.867 (18)	C15—C16	1.367 (3)
N6—C13	1.2950 (18)	C15—H15A	0.93
N7—C14	1.336 (2)	C16—C17	1.371 (3)
N7—C15	1.344 (2)	C16—H16A	0.93
N8—C20	1.338 (2)	C17—C18	1.378 (2)
N8—C19	1.3478 (19)	C17—H17A	0.93
C1—C2	1.373 (2)	C18—H18A	0.93
C1—H1A	0.93	C19—C23	1.391 (2)
C2—C3	1.372 (2)	C20—C21	1.373 (2)
C2—H2A	0.93	C20—H20A	0.93
C3—C4	1.374 (2)	C21—C22	1.364 (2)
C3—H3A	0.93	C21—H21A	0.93
C4—C5	1.388 (2)	C22—C23	1.377 (2)
C4—H4A	0.93	C22—H22A	0.93
C5—C6	1.489 (2)	C23—H23A	0.93
C6—C7	1.4903 (19)
C1—N1—C5	117.49 (13)	C11—C10—H10A	120.6
C8—N2—C7	117.01 (14)	C10—C11—C7	119.06 (16)
C6—N3—N4	119.03 (13)	C10—C11—H11A	120.5
N3—N4—C12	117.19 (13)	C7—C11—H11A	120.5
N3—N4—H1N4	121.5 (12)	O1—C12—N4	125.56 (14)
C12—N4—H1N4	120.0 (12)	O1—C12—N5	120.93 (15)
N6—N5—C12	120.07 (13)	N4—C12—N5	113.51 (13)
N6—N5—H1N5	120.7 (12)	N6—C13—C19	128.00 (13)
C12—N5—H1N5	118.9 (12)	N6—C13—C14	113.27 (12)
C13—N6—N5	120.05 (12)	C19—C13—C14	118.70 (12)
C14—N7—C15	116.40 (15)	N7—C14—C18	123.11 (15)
C20—N8—C19	117.23 (14)	N7—C14—C13	116.49 (13)
N1—C1—C2	124.33 (15)	C18—C14—C13	120.39 (14)
N1—C1—H1A	117.8	N7—C15—C16	124.07 (17)
C2—C1—H1A	117.8	N7—C15—H15A	118.0
C3—C2—C1	117.69 (15)	C16—C15—H15A	118.0
C3—C2—H2A	121.2	C15—C16—C17	118.62 (16)
C1—C2—H2A	121.2	C15—C16—H16A	120.7
C2—C3—C4	119.45 (16)	C17—C16—H16A	120.7
C2—C3—H3A	120.3	C16—C17—C18	118.59 (17)
C4—C3—H3A	120.3	C16—C17—H17A	120.7
C3—C4—C5	119.40 (15)	C18—C17—H17A	120.7
C3—C4—H4A	120.3	C14—C18—C17	119.18 (16)
C5—C4—H4A	120.3	C14—C18—H18A	120.4
N1—C5—C4	121.56 (14)	C17—C18—H18A	120.4
N1—C5—C6	117.81 (13)	N8—C19—C23	121.96 (14)
C4—C5—C6	120.61 (13)	N8—C19—C13	118.11 (12)
N3—C6—C5	128.10 (13)	C23—C19—C13	119.87 (13)
N3—C6—C7	112.55 (13)	N8—C20—C21	123.79 (16)
C5—C6—C7	119.35 (13)	N8—C20—H20A	118.1
N2—C7—C11	122.50 (14)	C21—C20—H20A	118.1
N2—C7—C6	116.47 (13)	C22—C21—C20	118.73 (16)
C11—C7—C6	121.01 (14)	C22—C21—H21A	120.6
N2—C8—C9	123.97 (17)	C20—C21—H21A	120.6
N2—C8—H8A	118.0	C21—C22—C23	119.19 (16)
C9—C8—H8A	118.0	C21—C22—H22A	120.4
C8—C9—C10	118.65 (15)	C23—C22—H22A	120.4
C8—C9—H9A	120.7	C22—C23—C19	119.07 (15)
C10—C9—H9A	120.7	C22—C23—H23A	120.5
C9—C10—C11	118.79 (16)	C19—C23—H23A	120.5
C9—C10—H10A	120.6
C6—N3—N4—C12	176.23 (14)	N3—N4—C12—N5	−176.32 (14)
C12—N5—N6—C13	−179.44 (15)	N6—N5—C12—O1	170.20 (16)
C5—N1—C1—C2	−0.8 (2)	N6—N5—C12—N4	−9.6 (2)
N1—C1—C2—C3	−1.5 (3)	N5—N6—C13—C19	−4.2 (2)
C1—C2—C3—C4	2.2 (3)	N5—N6—C13—C14	177.75 (13)
C2—C3—C4—C5	−0.6 (3)	C15—N7—C14—C18	−1.2 (2)
C1—N1—C5—C4	2.5 (2)	C15—N7—C14—C13	177.14 (14)
C1—N1—C5—C6	−179.07 (13)	N6—C13—C14—N7	−123.38 (15)
C3—C4—C5—N1	−1.9 (2)	C19—C13—C14—N7	58.41 (19)
C3—C4—C5—C6	179.78 (15)	N6—C13—C14—C18	55.03 (19)
N4—N3—C6—C5	0.9 (2)	C19—C13—C14—C18	−123.18 (16)
N4—N3—C6—C7	−178.74 (13)	C14—N7—C15—C16	1.4 (3)
N1—C5—C6—N3	−24.3 (2)	N7—C15—C16—C17	−0.5 (3)
C4—C5—C6—N3	154.11 (16)	C15—C16—C17—C18	−0.6 (3)
N1—C5—C6—C7	155.27 (13)	N7—C14—C18—C17	0.1 (2)
C4—C5—C6—C7	−26.3 (2)	C13—C14—C18—C17	−178.15 (15)
C8—N2—C7—C11	1.2 (2)	C16—C17—C18—C14	0.8 (3)
C8—N2—C7—C6	−177.49 (14)	C20—N8—C19—C23	−1.2 (2)
N3—C6—C7—N2	140.69 (15)	C20—N8—C19—C13	−178.51 (15)
C5—C6—C7—N2	−39.0 (2)	N6—C13—C19—N8	21.5 (2)
N3—C6—C7—C11	−38.0 (2)	C14—C13—C19—N8	−160.62 (13)
C5—C6—C7—C11	142.35 (15)	N6—C13—C19—C23	−155.87 (15)
C7—N2—C8—C9	0.2 (3)	C14—C13—C19—C23	22.0 (2)
N2—C8—C9—C10	−1.3 (3)	C19—N8—C20—C21	−0.2 (3)
C8—C9—C10—C11	1.1 (3)	N8—C20—C21—C22	1.6 (3)
C9—C10—C11—C7	0.2 (2)	C20—C21—C22—C23	−1.6 (3)
N2—C7—C11—C10	−1.4 (2)	C21—C22—C23—C19	0.3 (3)
C6—C7—C11—C10	177.24 (14)	N8—C19—C23—C22	1.2 (2)
N3—N4—C12—O1	3.9 (3)	C13—C19—C23—C22	178.43 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N1	0.92 (2)	2.03 (2)	2.707 (2)	130 (2)
N4—H1N4···N6	0.92 (2)	2.25 (2)	2.613 (2)	103 (1)
N5—H1N5···N8	0.87 (2)	2.04 (2)	2.702 (2)	132 (2)
C2—H2A···O1^i	0.93	2.55	3.213 (2)	128
C4—H4A···N2	0.93	2.60	2.982 (2)	105
C17—H17A···O1^i	0.93	2.53	3.348 (2)	146
C8—H8A···Cg^ii	0.93	2.78	3.466 (2)	131

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