1,5-Bis(1-phenyl­ethyl­idene)carbonohydrazide

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].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.148
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C4     -C9            1.37 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H17    ..  H17     ..       2.12 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3     ..  H3C     ..       1.94 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          4
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT128_ALERT_4_G Alternate Setting of Space-group P2/c    .......      P2/n

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

All H atoms were placed in geometrically idealized positions (N—H = 0.86 and C—H = 0.93–0.96 Å) and treated as riding on their parent atoms, with U_iso(H) = 1.2–1.5U_eq(C, N).

Computing details

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

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

1,5-Bis(1-phenylethylidene)carbonohydrazide

Crystal data

C17H18N4O	F(000) = 624
Mr = 294.35	Dx = 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) Å^3	Block, colourless
Z = 4	0.50 × 0.31 × 0.25 mm

Data collection

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

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0747P)^2] where P = (Fo^2 + 2Fc^2)/3
2757 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.13 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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···O5^i	0.96	2.53	3.405 (3)	151
N2—H2···O5^ii	0.86	2.11	2.955 (3)	166

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