2,2'-(Biphenyl-2,2'-diyldi-oxy)diaceto-hydrazide.

In the mol-ecule of the title compound, C(16)H(18)N(4)O(4), the dihedral angle between the mean planes of the two benzene rings is 56.76 (5)°. The crystal structure reveals extensive inter-molecular hydrogen bonds between carbonyl O atoms and primary amines, as well as between primary and secondary amines of hydrazide, forming rings of R(2) (2)(10) and R(2) (2)(6) motifs, respectively. The structure is further stabilized by intra-molecular and non-classical hydrogen bonds of the types N-H⋯O and C-H⋯O, respectively. The structure does not show any π-π inter-actions.

Related literature

For related literature see: Dekeyser et al. (2003 ▶); Ali et al. (2008 ▶); Baudry et al. (2006 ▶); Bhat et al. (1974 ▶); Etter (1990 ▶); Kakefuda et al. (2002 ▶); Litvinchuk et al. (2004 ▶); Priebe et al. (2008 ▶); Sisson et al. (2006 ▶); Thaker & Patel (2008 ▶); Yan et al. (1993 ▶).

Experimental

Crystal data

C16H18N4O4

M = 330.34

Triclinic,

a = 8.4041 (17) Å

b = 9.7148 (19) Å

c = 10.465 (2) Å

α = 99.27 (3)°

β = 92.50 (3)°

γ = 113.85 (3)°

V = 765.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 153 (2) K

0.31 × 0.29 × 0.22 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.968, T max = 0.977

5673 measured reflections

2695 independent reflections

2440 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.05

2695 reflections

237 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014864/pv2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014864/pv2081Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18N4O4	Z = 2
Mr = 330.34	F000 = 348
Triclinic, P1	Dx = 1.433 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.4041 (17) Å	Cell parameters from 2518 reflections
b = 9.7148 (19) Å	θ = 2.7–26.4º
c = 10.465 (2) Å	µ = 0.11 mm−1
α = 99.27 (3)º	T = 153 (2) K
β = 92.50 (3)º	Chip, colorless
γ = 113.85 (3)º	0.31 × 0.29 × 0.22 mm
V = 765.7 (3) Å3

Rigaku Mercury CCD diffractometer	2695 independent reflections
Radiation source: Sealed Tube	2440 reflections with I > 2σ(I)
Monochromator: Graphite Monochromator	Rint = 0.009
Detector resolution: 14.6306 pixels mm-1	θmax = 25.2º
T = 153(2) K	θmin = 2.0º
ω scans	h = −10→9
Absorption correction: multi-scan(REQAB; Jacobson, 1998)	k = −10→11
Tmin = 0.968, Tmax = 0.977	l = −12→12
5673 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.3477P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2695 reflections	Δρmax = 0.20 e Å−3
237 parameters	Δρmin = −0.20 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.32268 (15)	−0.23766 (13)	−0.20890 (9)	0.0317 (3)
O2	0.26996 (14)	−0.02884 (11)	0.08294 (9)	0.0263 (2)
O3	0.33765 (13)	0.10884 (10)	0.50896 (8)	0.0242 (2)
O4	0.41183 (15)	0.35080 (12)	0.81794 (9)	0.0313 (3)
N1	0.28627 (18)	−0.42946 (14)	−0.03033 (12)	0.0282 (3)
H1A	0.389 (2)	−0.419 (2)	0.0137 (16)	0.034*
H1B	0.293 (2)	−0.452 (2)	−0.1191 (14)	0.034*
N2	0.28707 (16)	−0.28115 (14)	−0.00437 (11)	0.0253 (3)
H2	0.253 (2)	−0.254 (2)	0.0732 (15)	0.035 (5)*
N3	0.41999 (16)	0.39435 (13)	0.61151 (11)	0.0236 (3)
H3	0.428 (2)	0.362 (2)	0.5272 (14)	0.038 (5)*
N4	0.46353 (18)	0.55390 (14)	0.64554 (12)	0.0271 (3)
H4A	0.544 (2)	0.5916 (19)	0.7182 (15)	0.032*
H4B	0.364 (2)	0.565 (2)	0.6732 (16)	0.032*
C1	0.29940 (17)	−0.19832 (16)	−0.09628 (12)	0.0216 (3)
C2	0.28191 (18)	−0.04884 (16)	−0.05358 (12)	0.0217 (3)
H2B	0.3851	0.0379	−0.0726	0.026*
H2C	0.1756	−0.0523	−0.1013	0.026*
C3	0.21044 (17)	0.07599 (15)	0.14010 (12)	0.0196 (3)
C4	0.20643 (18)	0.19491 (15)	0.08338 (13)	0.0224 (3)
H4C	0.2437	0.2059	−0.0002	0.027*
C5	0.14735 (18)	0.29724 (16)	0.15019 (14)	0.0253 (3)
H5A	0.1430	0.3779	0.1116	0.030*
C6	0.09474 (18)	0.28244 (15)	0.27275 (14)	0.0246 (3)
H6A	0.0544	0.3527	0.3181	0.029*
C7	0.10118 (17)	0.16440 (15)	0.32919 (13)	0.0212 (3)
H7A	0.0664	0.1557	0.4137	0.025*
C8	0.15766 (16)	0.05875 (14)	0.26424 (12)	0.0187 (3)
C9	0.15926 (17)	−0.07024 (15)	0.32413 (12)	0.0187 (3)
C10	0.25033 (17)	−0.04279 (15)	0.44785 (12)	0.0189 (3)
C11	0.25260 (18)	−0.16331 (16)	0.50320 (13)	0.0229 (3)
H11A	0.3164	−0.1431	0.5864	0.028*
C12	0.1608 (2)	−0.31304 (16)	0.43565 (14)	0.0261 (3)
H12A	0.1631	−0.3956	0.4724	0.031*
C13	0.0658 (2)	−0.34330 (16)	0.31497 (14)	0.0271 (3)
H13A	0.0014	−0.4462	0.2700	0.033*
C14	0.06546 (18)	−0.22235 (15)	0.26023 (13)	0.0229 (3)
H14A	0.0000	−0.2436	0.1776	0.028*
C15	0.36921 (19)	0.14095 (16)	0.64783 (12)	0.0242 (3)
H15A	0.4720	0.1228	0.6757	0.029*
H15B	0.2663	0.0717	0.6837	0.029*
C16	0.40281 (17)	0.30626 (16)	0.69949 (12)	0.0218 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0463 (7)	0.0413 (6)	0.0184 (5)	0.0285 (5)	0.0086 (4)	0.0069 (4)
O2	0.0425 (6)	0.0299 (5)	0.0148 (5)	0.0231 (5)	0.0048 (4)	0.0048 (4)
O3	0.0358 (6)	0.0189 (5)	0.0135 (4)	0.0073 (4)	0.0008 (4)	0.0026 (4)
O4	0.0438 (6)	0.0325 (6)	0.0156 (5)	0.0157 (5)	0.0017 (4)	0.0004 (4)
N1	0.0377 (7)	0.0248 (6)	0.0259 (6)	0.0165 (6)	0.0055 (5)	0.0054 (5)
N2	0.0358 (7)	0.0251 (6)	0.0193 (6)	0.0164 (5)	0.0066 (5)	0.0051 (5)
N3	0.0307 (6)	0.0196 (6)	0.0179 (6)	0.0087 (5)	0.0049 (5)	0.0008 (4)
N4	0.0358 (7)	0.0210 (6)	0.0224 (6)	0.0111 (5)	0.0055 (5)	0.0004 (5)
C1	0.0205 (6)	0.0282 (7)	0.0173 (6)	0.0112 (6)	0.0020 (5)	0.0045 (5)
C2	0.0250 (7)	0.0252 (7)	0.0150 (6)	0.0103 (6)	0.0024 (5)	0.0051 (5)
C3	0.0210 (6)	0.0182 (6)	0.0184 (6)	0.0079 (5)	−0.0007 (5)	0.0016 (5)
C4	0.0239 (7)	0.0216 (7)	0.0204 (6)	0.0071 (5)	0.0010 (5)	0.0075 (5)
C5	0.0266 (7)	0.0184 (7)	0.0311 (7)	0.0081 (6)	−0.0006 (6)	0.0094 (6)
C6	0.0265 (7)	0.0183 (7)	0.0300 (7)	0.0116 (6)	0.0013 (6)	0.0026 (5)
C7	0.0215 (7)	0.0202 (7)	0.0208 (6)	0.0080 (5)	0.0014 (5)	0.0032 (5)
C8	0.0197 (6)	0.0159 (6)	0.0185 (6)	0.0058 (5)	−0.0006 (5)	0.0029 (5)
C9	0.0217 (6)	0.0187 (7)	0.0179 (6)	0.0101 (5)	0.0051 (5)	0.0044 (5)
C10	0.0222 (6)	0.0173 (6)	0.0169 (6)	0.0080 (5)	0.0051 (5)	0.0025 (5)
C11	0.0281 (7)	0.0259 (7)	0.0183 (6)	0.0138 (6)	0.0036 (5)	0.0071 (5)
C12	0.0351 (8)	0.0219 (7)	0.0271 (7)	0.0154 (6)	0.0063 (6)	0.0102 (6)
C13	0.0337 (8)	0.0175 (7)	0.0289 (7)	0.0102 (6)	0.0016 (6)	0.0030 (5)
C14	0.0279 (7)	0.0207 (7)	0.0200 (6)	0.0105 (6)	0.0003 (5)	0.0028 (5)
C15	0.0325 (7)	0.0252 (7)	0.0134 (6)	0.0104 (6)	0.0021 (5)	0.0041 (5)
C16	0.0204 (6)	0.0251 (7)	0.0176 (6)	0.0080 (5)	0.0017 (5)	0.0019 (5)

O1—C1	1.2284 (17)	C4—H4C	0.9500
O2—C3	1.3736 (16)	C5—C6	1.385 (2)
O2—C2	1.4242 (15)	C5—H5A	0.9500
O3—C10	1.3779 (17)	C6—C7	1.3901 (19)
O3—C15	1.4259 (15)	C6—H6A	0.9500
O4—C16	1.2338 (16)	C7—C8	1.3922 (19)
N1—N2	1.4198 (17)	C7—H7A	0.9500
N1—H1A	0.925 (14)	C8—C9	1.4931 (18)
N1—H1B	0.930 (14)	C9—C14	1.3949 (19)
N2—C1	1.3320 (18)	C9—C10	1.4037 (19)
N2—H2	0.907 (14)	C10—C11	1.3937 (19)
N3—C16	1.3291 (18)	C11—C12	1.387 (2)
N3—N4	1.4196 (17)	C11—H11A	0.9500
N3—H3	0.904 (14)	C12—C13	1.386 (2)
N4—H4A	0.914 (14)	C12—H12A	0.9500
N4—H4B	0.936 (14)	C13—C14	1.3888 (19)
C1—C2	1.5164 (19)	C13—H13A	0.9500
C2—H2B	0.9900	C14—H14A	0.9500
C2—H2C	0.9900	C15—C16	1.514 (2)
C3—C4	1.3924 (19)	C15—H15A	0.9900
C3—C8	1.4046 (18)	C15—H15B	0.9900
C4—C5	1.389 (2)
C3—O2—C2	119.52 (10)	C7—C6—H6A	120.1
C10—O3—C15	117.33 (10)	C6—C7—C8	121.29 (12)
N2—N1—H1A	105.6 (11)	C6—C7—H7A	119.4
N2—N1—H1B	106.5 (11)	C8—C7—H7A	119.4
H1A—N1—H1B	107.7 (15)	C7—C8—C3	117.98 (12)
C1—N2—N1	122.76 (12)	C7—C8—C9	120.86 (11)
C1—N2—H2	119.5 (11)	C3—C8—C9	121.16 (12)
N1—N2—H2	116.3 (11)	C14—C9—C10	117.93 (12)
C16—N3—N4	123.00 (11)	C14—C9—C8	120.81 (11)
C16—N3—H3	121.4 (12)	C10—C9—C8	121.23 (12)
N4—N3—H3	114.3 (12)	O3—C10—C11	122.79 (11)
N3—N4—H4A	106.8 (11)	O3—C10—C9	116.07 (11)
N3—N4—H4B	107.6 (11)	C11—C10—C9	121.13 (12)
H4A—N4—H4B	105.1 (15)	C12—C11—C10	119.35 (12)
O1—C1—N2	123.62 (13)	C12—C11—H11A	120.3
O1—C1—C2	120.88 (12)	C10—C11—H11A	120.3
N2—C1—C2	115.50 (11)	C13—C12—C11	120.59 (13)
O2—C2—C1	108.04 (11)	C13—C12—H12A	119.7
O2—C2—H2B	110.1	C11—C12—H12A	119.7
C1—C2—H2B	110.1	C12—C13—C14	119.61 (13)
O2—C2—H2C	110.1	C12—C13—H13A	120.2
C1—C2—H2C	110.1	C14—C13—H13A	120.2
H2B—C2—H2C	108.4	C13—C14—C9	121.34 (12)
O2—C3—C4	123.65 (12)	C13—C14—H14A	119.3
O2—C3—C8	115.15 (11)	C9—C14—H14A	119.3
C4—C3—C8	121.17 (12)	O3—C15—C16	109.67 (11)
C5—C4—C3	119.38 (13)	O3—C15—H15A	109.7
C5—C4—H4C	120.3	C16—C15—H15A	109.7
C3—C4—H4C	120.3	O3—C15—H15B	109.7
C6—C5—C4	120.42 (12)	C16—C15—H15B	109.7
C6—C5—H5A	119.8	H15A—C15—H15B	108.2
C4—C5—H5A	119.8	O4—C16—N3	124.25 (13)
C5—C6—C7	119.76 (13)	O4—C16—C15	119.25 (12)
C5—C6—H6A	120.1	N3—C16—C15	116.49 (11)
N1—N2—C1—O1	−5.0 (2)	C7—C8—C9—C10	−55.87 (18)
N1—N2—C1—C2	174.76 (12)	C3—C8—C9—C10	125.09 (14)
C3—O2—C2—C1	−163.98 (11)	C15—O3—C10—C11	−25.80 (18)
O1—C1—C2—O2	−175.55 (12)	C15—O3—C10—C9	155.02 (12)
N2—C1—C2—O2	4.71 (16)	C14—C9—C10—O3	−178.44 (11)
C2—O2—C3—C4	−18.76 (19)	C8—C9—C10—O3	−0.38 (18)
C2—O2—C3—C8	163.23 (12)	C14—C9—C10—C11	2.38 (19)
O2—C3—C4—C5	−178.61 (12)	C8—C9—C10—C11	−179.57 (12)
C8—C3—C4—C5	−0.7 (2)	O3—C10—C11—C12	179.79 (12)
C3—C4—C5—C6	0.7 (2)	C9—C10—C11—C12	−1.1 (2)
C4—C5—C6—C7	0.0 (2)	C10—C11—C12—C13	−0.8 (2)
C5—C6—C7—C8	−0.8 (2)	C11—C12—C13—C14	1.2 (2)
C6—C7—C8—C3	0.82 (19)	C12—C13—C14—C9	0.1 (2)
C6—C7—C8—C9	−178.24 (12)	C10—C9—C14—C13	−1.9 (2)
O2—C3—C8—C7	178.01 (11)	C8—C9—C14—C13	−179.96 (13)
C4—C3—C8—C7	−0.05 (19)	C10—O3—C15—C16	−159.34 (11)
O2—C3—C8—C9	−2.93 (18)	N4—N3—C16—O4	4.7 (2)
C4—C3—C8—C9	179.01 (12)	N4—N3—C16—C15	−175.62 (12)
C7—C8—C9—C14	122.12 (14)	O3—C15—C16—O4	171.27 (12)
C3—C8—C9—C14	−56.91 (18)	O3—C15—C16—N3	−8.42 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.924 (14)	2.192 (15)	3.059 (2)	155.7 (15)
N1—H1B···O4ii	0.930 (14)	2.510 (17)	3.0112 (18)	114.1 (13)
N3—H3···N4iii	0.900 (13)	2.191 (15)	2.9524 (18)	141.9 (14)
N4—H4B···O1iv	0.936 (14)	2.267 (16)	2.9873 (18)	133.3 (14)
N1—H1B···O1	0.930 (14)	2.348 (17)	2.7873 (18)	108.6 (13)
N2—H2···O2	0.906 (14)	2.118 (17)	2.5375 (16)	107.1 (13)
N3—H3···O3	0.900 (13)	2.230 (16)	2.5977 (17)	103.9 (12)
C5—H5A···N1v	0.95	2.53	3.359 (2)	146
C11—H11A···O1vi	0.95	2.47	3.292 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.924 (14)	2.192 (15)	3.059 (2)	155.7 (15)
N1—H1B⋯O4ii	0.930 (14)	2.510 (17)	3.0112 (18)	114.1 (13)
N3—H3⋯N4iii	0.900 (13)	2.191 (15)	2.9524 (18)	141.9 (14)
N4—H4B⋯O1iv	0.936 (14)	2.267 (16)	2.9873 (18)	133.3 (14)
N1—H1B⋯O1	0.930 (14)	2.348 (17)	2.7873 (18)	108.6 (13)
N2—H2⋯O2	0.906 (14)	2.118 (17)	2.5375 (16)	107.1 (13)
N3—H3⋯O3	0.900 (13)	2.230 (16)	2.5977 (17)	103.9 (12)
C5—H5A⋯N1v	0.95	2.53	3.359 (2)	146
C11—H11A⋯O1vi	0.95	2.47	3.292 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .