1,5-Bis(1-phenyl­ethyl­idene)carbonohydrazide

Kong, L.; Qiao, Y.; Gao, Z.; Ju, X.

doi:10.1107/S1600536810042121

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2901

https://doi.org/10.1107/S1600536810042121

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1,5-Bis(1-phenylethylidene)carbonohydrazide

Lingqian Kong,^a ^* Yan Qiao,^a Zhiqing Gao ^a and Xiuping Ju ^a

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 12 October 2010; accepted 17 October 2010; online 23 October 2010)

In the title molecule, C₁₇H₁₈N₄O, the two phenyl rings form a dihedral angle of 18.15 (17)°. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. Weak intermolecular C—H⋯O interactions further link the dimers into chains running along [010].

Related literature

For related structures, see: Qiao et al. (2010 ); Kolb et al. (1994 4); Meyers et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₈N₄O
M_r = 294.35
Monoclinic, P 2/n
a = 12.9393 (12) Å
b = 5.4858 (5) Å
c = 22.703 (2) Å
β = 104.681 (1)°
V = 1558.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.31 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.980
7406 measured reflections
2757 independent reflections
1389 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.148
S = 0.90
2757 reflections
201 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3C⋯O5ⁱ	0.96	2.53	3.405 (3)	151
N2—H2⋯O5ⁱⁱ	0.86	2.11	2.955 (3)	166
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042121/cv2776sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042121/cv2776Isup2.hkl

checkCIF report

Comment top

In continuation of our study of Schiff bases and carbonohydrazides (Qiao et al., 2010), we obtained the title compound, (I), and present here its crystal structure.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in bis(4-methoxyphenylmethine)carbonohydrazide (Kolb et al., 1994) and bis(3-fluorophenylmethine)carbonohydrazide (Meyers et al., 1995). The C=N bond lengths are 1.282 (3) ° and 1.286 (3)° (C10=N1 and C2=N4, respectively) showing their double-bond character. Two phenyl rings - C4-C9 and C12—C17, respectively - form a dihedral angle of 18.15 (17)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers, and weak intermolecular C—H···O interactions (Table 1) link further these dimers into chains running in direction [010].

Related literature top

For related structures, see: Qiao et al. (2010); Kolb et al. (19944); Meyers et al. (1995).

Experimental top

Acetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash under sovlent-free condtions. After stirring for 3 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid.

Structure description top

In continuation of our study of Schiff bases and carbonohydrazides (Qiao et al., 2010), we obtained the title compound, (I), and present here its crystal structure.

For related structures, see: Qiao et al. (2010); Kolb et al. (19944); Meyers et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

1,5-Bis(1-phenylethylidene)carbonohydrazide top

Crystal data top

C₁₇H₁₈N₄O	F(000) = 624
M_r = 294.35	D_x = 1.254 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.9393 (12) Å	Cell parameters from 1233 reflections
b = 5.4858 (5) Å	θ = 2.9–21.2°
c = 22.703 (2) Å	µ = 0.08 mm⁻¹
β = 104.681 (1)°	T = 298 K
V = 1558.9 (2) Å³	Block, colourless
Z = 4	0.50 × 0.31 × 0.25 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
phi and ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.960, T_max = 0.980	k = −6→6
7406 measured reflections	l = −26→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0747P)²] where P = (F_o² + 2F_c²)/3
2757 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₇H₁₈N₄O	V = 1558.9 (2) Å³
M_r = 294.35	Z = 4
Monoclinic, P2/n	Mo Kα radiation
a = 12.9393 (12) Å	µ = 0.08 mm⁻¹
b = 5.4858 (5) Å	T = 298 K
c = 22.703 (2) Å	0.50 × 0.31 × 0.25 mm
β = 104.681 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2757 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1389 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.980	R_int = 0.048
7406 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.148	H-atom parameters constrained
S = 0.90	Δρ_max = 0.18 e Å⁻³
2757 reflections	Δρ_min = −0.13 e Å⁻³
201 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O5	0.86754 (12)	0.0739 (3)	0.46156 (9)	0.0764 (6)
N1	0.96224 (16)	0.4666 (4)	0.58368 (10)	0.0631 (6)
N2	0.96359 (15)	0.2825 (4)	0.54321 (10)	0.0679 (6)
H2	1.0196	0.1938	0.5466	0.082*
N3	0.79610 (14)	0.4095 (4)	0.49611 (9)	0.0668 (6)
H3	0.8087	0.5299	0.5212	0.080*
N4	0.69764 (15)	0.3902 (4)	0.45574 (9)	0.0596 (6)
C1	0.87369 (18)	0.2428 (5)	0.49730 (13)	0.0614 (7)
C2	0.63193 (18)	0.5649 (4)	0.45685 (10)	0.0542 (6)
C3	0.65842 (18)	0.7846 (5)	0.49701 (13)	0.0795 (8)
H3A	0.6503	0.7461	0.5368	0.119*
H3B	0.6111	0.9157	0.4800	0.119*
H3C	0.7309	0.8329	0.5000	0.119*
C4	0.52443 (18)	0.5423 (5)	0.41536 (11)	0.0551 (6)
C5	0.4445 (2)	0.7041 (6)	0.41690 (14)	0.0928 (10)
H5	0.4592	0.8337	0.4442	0.111*
C6	0.3434 (2)	0.6811 (7)	0.37943 (17)	0.1109 (12)
H6	0.2909	0.7936	0.3818	0.133*
C7	0.3200 (2)	0.4948 (7)	0.33899 (14)	0.0934 (10)
H7	0.2518	0.4792	0.3133	0.112*
C8	0.3977 (2)	0.3314 (6)	0.33648 (14)	0.1002 (11)
H8	0.3828	0.2028	0.3089	0.120*
C9	0.4984 (2)	0.3561 (6)	0.37467 (13)	0.0836 (9)
H9	0.5503	0.2416	0.3726	0.100*
C10	1.04459 (19)	0.5073 (5)	0.62766 (12)	0.0618 (7)
C11	1.14821 (18)	0.3686 (5)	0.63824 (12)	0.0783 (8)
H11A	1.1447	0.2260	0.6622	0.117*
H11B	1.2060	0.4706	0.6595	0.117*
H11C	1.1600	0.3207	0.5998	0.117*
C12	1.03396 (18)	0.7066 (5)	0.66970 (11)	0.0613 (7)
C13	0.9504 (2)	0.8704 (6)	0.65627 (13)	0.0774 (8)
H13	0.8986	0.8551	0.6197	0.093*
C14	0.9416 (2)	1.0546 (6)	0.69527 (16)	0.0880 (9)
H14	0.8835	1.1601	0.6853	0.106*
C15	1.0179 (3)	1.0851 (6)	0.74911 (15)	0.0845 (9)
H15	1.0131	1.2126	0.7753	0.101*
C16	1.1002 (2)	0.9256 (7)	0.76324 (14)	0.0906 (10)
H16	1.1521	0.9426	0.7998	0.109*
C17	1.1083 (2)	0.7385 (6)	0.72431 (14)	0.0815 (9)
H17	1.1655	0.6309	0.7352	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0605 (11)	0.0704 (14)	0.0975 (14)	0.0118 (9)	0.0187 (10)	−0.0167 (11)
N1	0.0542 (12)	0.0619 (15)	0.0726 (14)	0.0052 (11)	0.0148 (11)	0.0028 (12)
N2	0.0497 (12)	0.0686 (16)	0.0815 (15)	0.0129 (11)	0.0094 (12)	0.0009 (13)
N3	0.0482 (12)	0.0621 (15)	0.0854 (15)	0.0119 (11)	0.0083 (11)	−0.0128 (12)
N4	0.0495 (11)	0.0583 (14)	0.0715 (13)	0.0102 (10)	0.0163 (10)	−0.0017 (11)
C1	0.0501 (15)	0.0579 (19)	0.0787 (18)	0.0091 (14)	0.0209 (14)	0.0069 (15)
C2	0.0537 (14)	0.0501 (17)	0.0622 (15)	0.0050 (12)	0.0208 (13)	0.0021 (13)
C3	0.0647 (16)	0.064 (2)	0.105 (2)	0.0061 (14)	0.0140 (15)	−0.0156 (17)
C4	0.0546 (14)	0.0531 (17)	0.0595 (15)	0.0097 (12)	0.0178 (12)	0.0005 (13)
C5	0.0669 (18)	0.080 (2)	0.120 (2)	0.0188 (16)	0.0031 (18)	−0.0300 (19)
C6	0.069 (2)	0.109 (3)	0.139 (3)	0.0329 (19)	−0.003 (2)	−0.027 (3)
C7	0.0665 (18)	0.113 (3)	0.089 (2)	0.014 (2)	−0.0036 (16)	−0.011 (2)
C8	0.086 (2)	0.109 (3)	0.093 (2)	0.022 (2)	−0.0016 (19)	−0.032 (2)
C9	0.0678 (18)	0.093 (2)	0.0825 (19)	0.0223 (16)	0.0058 (16)	−0.0227 (19)
C10	0.0493 (14)	0.0676 (19)	0.0676 (17)	0.0015 (13)	0.0133 (14)	0.0164 (15)
C11	0.0550 (14)	0.091 (2)	0.0872 (19)	0.0137 (15)	0.0146 (14)	0.0071 (17)
C12	0.0480 (14)	0.0679 (19)	0.0677 (17)	−0.0023 (13)	0.0139 (13)	0.0092 (15)
C13	0.0674 (17)	0.076 (2)	0.083 (2)	0.0100 (16)	0.0071 (15)	0.0017 (18)
C14	0.079 (2)	0.081 (2)	0.104 (2)	0.0140 (17)	0.023 (2)	−0.001 (2)
C15	0.083 (2)	0.082 (2)	0.094 (2)	−0.0121 (18)	0.0339 (19)	−0.0083 (19)
C16	0.0691 (19)	0.116 (3)	0.083 (2)	−0.004 (2)	0.0131 (17)	−0.006 (2)
C17	0.0582 (16)	0.095 (2)	0.087 (2)	0.0092 (16)	0.0111 (16)	−0.0002 (19)

Geometric parameters (Å, º) top

O5—C1	1.221 (3)	C7—H7	0.9300
N1—C10	1.282 (3)	C8—C9	1.377 (3)
N1—N2	1.368 (3)	C8—H8	0.9300
N2—C1	1.368 (3)	C9—H9	0.9300
N2—H2	0.8600	C10—C12	1.480 (4)
N3—C1	1.353 (3)	C10—C11	1.507 (3)
N3—N4	1.372 (2)	C11—H11A	0.9600
N3—H3	0.8600	C11—H11B	0.9600
N4—C2	1.286 (3)	C11—H11C	0.9600
C2—C4	1.474 (3)	C12—C17	1.374 (3)
C2—C3	1.498 (3)	C12—C13	1.379 (3)
C3—H3A	0.9600	C13—C14	1.367 (4)
C3—H3B	0.9600	C13—H13	0.9300
C3—H3C	0.9600	C14—C15	1.373 (4)
C4—C9	1.361 (3)	C14—H14	0.9300
C4—C5	1.370 (3)	C15—C16	1.353 (4)
C5—C6	1.374 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.376 (4)
C6—C7	1.356 (4)	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.358 (4)

C10—N1—N2	120.1 (2)	C7—C8—H8	120.0
C1—N2—N1	118.4 (2)	C9—C8—H8	120.0
C1—N2—H2	120.8	C4—C9—C8	122.2 (3)
N1—N2—H2	120.8	C4—C9—H9	118.9
C1—N3—N4	121.3 (2)	C8—C9—H9	118.9
C1—N3—H3	119.3	N1—C10—C12	115.9 (2)
N4—N3—H3	119.3	N1—C10—C11	124.5 (3)
C2—N4—N3	115.9 (2)	C12—C10—C11	119.6 (2)
O5—C1—N3	125.2 (2)	C10—C11—H11A	109.5
O5—C1—N2	121.8 (2)	C10—C11—H11B	109.5
N3—C1—N2	113.0 (3)	H11A—C11—H11B	109.5
N4—C2—C4	116.5 (2)	C10—C11—H11C	109.5
N4—C2—C3	124.2 (2)	H11A—C11—H11C	109.5
C4—C2—C3	119.3 (2)	H11B—C11—H11C	109.5
C2—C3—H3A	109.5	C17—C12—C13	116.5 (3)
C2—C3—H3B	109.5	C17—C12—C10	121.2 (2)
H3A—C3—H3B	109.5	C13—C12—C10	122.3 (2)
C2—C3—H3C	109.5	C14—C13—C12	121.8 (3)
H3A—C3—H3C	109.5	C14—C13—H13	119.1
H3B—C3—H3C	109.5	C12—C13—H13	119.1
C9—C4—C5	116.4 (2)	C13—C14—C15	120.5 (3)
C9—C4—C2	121.9 (2)	C13—C14—H14	119.7
C5—C4—C2	121.7 (2)	C15—C14—H14	119.7
C4—C5—C6	122.1 (3)	C16—C15—C14	118.5 (3)
C4—C5—H5	119.0	C16—C15—H15	120.7
C6—C5—H5	119.0	C14—C15—H15	120.7
C7—C6—C5	120.2 (3)	C15—C16—C17	120.9 (3)
C7—C6—H6	119.9	C15—C16—H16	119.5
C5—C6—H6	119.9	C17—C16—H16	119.5
C6—C7—C8	119.0 (3)	C12—C17—C16	121.7 (3)
C6—C7—H7	120.5	C12—C17—H17	119.2
C8—C7—H7	120.5	C16—C17—H17	119.2
C7—C8—C9	120.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···O5ⁱ	0.96	2.53	3.405 (3)	151
N2—H2···O5ⁱⁱ	0.86	2.11	2.955 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₄O
M_r	294.35
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	298
a, b, c (Å)	12.9393 (12), 5.4858 (5), 22.703 (2)
β (°)	104.681 (1)
V (Å³)	1558.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.31 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	7406, 2757, 1389
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.148, 0.90
No. of reflections	2757
No. of parameters	201
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···O5ⁱ	0.96	2.53	3.405 (3)	151.0
N2—H2···O5ⁱⁱ	0.86	2.11	2.955 (3)	166.3

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

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

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