Crystal structure of (Z)-2-[(E)-2-benzyl­idene­hydrazin-1-yl­idene]-1,2-di­phenyl­ethanone

The title compound has an almost planar 1,2-di­benzyl­idenehydrazine backbone with an approximately orthogonal planar phenyl ethanone substituent on one of the imine C atoms. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds and C—H...π inter­actions, forming a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.094
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.53 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H35    ..  O1      ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H32    ..  O1      ..       2.68 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         74 %

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  F2dd       Fdd2    Note
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSCAL (T. Roisnel, local program), SHELXL2014 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010) and WinGX (Farrugia, 2012).

(Z)-2-[(E)-2-Benzylidenehydrazin-1-ylidene]-1,2-diphenylethanone

Crystal data

C21H16N2O	F(000) = 2624
Mr = 312.36	Dx = 1.240 Mg m^−3
Orthorhombic, F2dd	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F -2d 2	Cell parameters from 2807 reflections
a = 8.1653 (3) Å	θ = 2.7–27.3°
b = 27.6113 (11) Å	µ = 0.08 mm^−1
c = 29.6818 (13) Å	T = 150 K
V = 6691.9 (5) Å^3	Prism, yellow
Z = 16	0.55 × 0.29 × 0.24 mm

Data collection

Bruker APEXII diffractometer	3036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→10
Tmin = 0.884, Tmax = 0.982	k = −35→24
8049 measured reflections	l = −38→38
3350 independent reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 4.1058P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3350 reflections	Δρmax = 0.18 e Å^−3
217 parameters	Δρmin = −0.16 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.

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

	x	y	z	Uiso*/Ueq
C11	0.4692 (3)	0.24563 (8)	0.36467 (7)	0.0255 (5)
C12	0.4156 (3)	0.28709 (9)	0.34210 (7)	0.0316 (5)
H12	0.4758	0.3164	0.3444	0.038*
C13	0.2746 (3)	0.28525 (11)	0.31643 (9)	0.0426 (7)
H13	0.2381	0.3134	0.3010	0.051*
C14	0.1865 (3)	0.24267 (12)	0.31313 (10)	0.0504 (8)
H14	0.0888	0.2418	0.2958	0.060*
C15	0.2393 (4)	0.20147 (11)	0.33483 (10)	0.0453 (7)
H15	0.1790	0.1722	0.3322	0.054*
C16	0.3810 (3)	0.20282 (9)	0.36059 (8)	0.0326 (6)
H16	0.4178	0.1744	0.3755	0.039*
C1	0.6212 (3)	0.24786 (8)	0.39198 (6)	0.0222 (4)
O1	0.7037 (2)	0.28433 (5)	0.39542 (5)	0.0300 (4)
C2	0.6774 (3)	0.20274 (8)	0.41744 (7)	0.0220 (5)
C21	0.6542 (3)	0.20065 (8)	0.46670 (6)	0.0234 (5)
C22	0.5622 (3)	0.23566 (9)	0.48904 (7)	0.0291 (5)
H22	0.5110	0.2608	0.4723	0.035*
C23	0.5449 (3)	0.23409 (10)	0.53561 (8)	0.0344 (6)
H23	0.4825	0.2582	0.5507	0.041*
C24	0.6182 (3)	0.19755 (11)	0.55991 (8)	0.0401 (6)
H24	0.6067	0.1966	0.5917	0.048*
C25	0.7083 (4)	0.16228 (11)	0.53816 (8)	0.0406 (7)
H25	0.7575	0.1369	0.5550	0.049*
C26	0.7272 (3)	0.16376 (9)	0.49169 (8)	0.0332 (6)
H26	0.7901	0.1396	0.4769	0.040*
N1	0.7555 (2)	0.16872 (7)	0.39690 (6)	0.0265 (4)
N2	0.7675 (2)	0.17867 (7)	0.35026 (6)	0.0255 (4)
C3	0.8450 (3)	0.14520 (8)	0.32965 (7)	0.0245 (5)
H3	0.8903	0.1192	0.3465	0.029*
C31	0.8657 (3)	0.14596 (8)	0.28078 (7)	0.0252 (5)
C32	0.9510 (3)	0.10863 (9)	0.25997 (8)	0.0307 (5)
H32	0.9991	0.0838	0.2777	0.037*
C33	0.9664 (3)	0.10743 (10)	0.21338 (8)	0.0383 (6)
H33	1.0228	0.0814	0.1993	0.046*
C34	0.9002 (3)	0.14389 (9)	0.18749 (8)	0.0371 (6)
H34	0.9115	0.1431	0.1556	0.045*
C35	0.8166 (3)	0.18203 (10)	0.20799 (8)	0.0346 (6)
H35	0.7721	0.2074	0.1902	0.041*
C36	0.7987 (3)	0.18291 (9)	0.25427 (8)	0.0294 (5)
H36	0.7406	0.2087	0.2682	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0250 (11)	0.0314 (12)	0.0200 (9)	0.0026 (11)	0.0015 (8)	0.0014 (8)
C12	0.0328 (13)	0.0337 (13)	0.0283 (11)	0.0066 (11)	−0.0003 (10)	0.0044 (10)
C13	0.0368 (15)	0.0525 (17)	0.0385 (14)	0.0136 (14)	−0.0061 (11)	0.0126 (12)
C14	0.0283 (15)	0.076 (2)	0.0472 (15)	−0.0018 (15)	−0.0157 (12)	0.0105 (15)
C15	0.0348 (15)	0.0542 (17)	0.0471 (15)	−0.0116 (14)	−0.0096 (12)	0.0049 (13)
C16	0.0298 (13)	0.0375 (14)	0.0304 (11)	−0.0016 (12)	−0.0019 (9)	0.0049 (10)
C1	0.0268 (11)	0.0233 (11)	0.0166 (8)	0.0035 (10)	0.0021 (8)	−0.0012 (8)
O1	0.0370 (10)	0.0233 (8)	0.0298 (8)	−0.0021 (8)	−0.0063 (7)	0.0013 (6)
C2	0.0214 (11)	0.0228 (10)	0.0217 (9)	−0.0008 (10)	−0.0023 (8)	0.0004 (8)
C21	0.0236 (12)	0.0262 (11)	0.0205 (9)	−0.0027 (9)	−0.0012 (8)	0.0029 (8)
C22	0.0292 (13)	0.0311 (13)	0.0268 (11)	0.0028 (11)	0.0008 (9)	0.0009 (9)
C23	0.0317 (14)	0.0428 (15)	0.0288 (12)	0.0041 (12)	0.0054 (10)	−0.0010 (10)
C24	0.0344 (14)	0.0655 (18)	0.0203 (10)	0.0006 (14)	0.0028 (10)	0.0063 (12)
C25	0.0372 (15)	0.0549 (17)	0.0297 (12)	0.0075 (14)	−0.0009 (10)	0.0153 (11)
C26	0.0347 (14)	0.0367 (14)	0.0284 (12)	0.0061 (12)	0.0004 (10)	0.0079 (10)
N1	0.0320 (11)	0.0263 (10)	0.0212 (9)	0.0019 (9)	−0.0025 (8)	0.0019 (7)
N2	0.0317 (11)	0.0248 (10)	0.0201 (9)	0.0012 (9)	−0.0014 (8)	−0.0013 (7)
C3	0.0258 (12)	0.0213 (11)	0.0265 (10)	−0.0013 (10)	−0.0021 (8)	0.0005 (9)
C31	0.0237 (12)	0.0250 (11)	0.0268 (10)	−0.0049 (10)	−0.0009 (9)	−0.0034 (9)
C32	0.0327 (14)	0.0296 (12)	0.0299 (12)	0.0014 (11)	0.0035 (9)	−0.0009 (9)
C33	0.0395 (16)	0.0419 (15)	0.0335 (13)	−0.0008 (13)	0.0100 (10)	−0.0070 (11)
C34	0.0386 (15)	0.0490 (16)	0.0238 (10)	−0.0104 (13)	0.0031 (10)	−0.0019 (10)
C35	0.0359 (14)	0.0378 (14)	0.0299 (12)	−0.0038 (12)	−0.0064 (10)	0.0054 (10)
C36	0.0319 (13)	0.0256 (12)	0.0307 (11)	−0.0002 (11)	−0.0049 (10)	0.0005 (9)

Geometric parameters (Å, º)

C11—C16	1.390 (3)	C23—H23	0.9500
C11—C12	1.397 (3)	C24—C25	1.381 (4)
C11—C1	1.483 (3)	C24—H24	0.9500
C12—C13	1.382 (4)	C25—C26	1.388 (3)
C12—H12	0.9500	C25—H25	0.9500
C13—C14	1.382 (4)	C26—H26	0.9500
C13—H13	0.9500	N1—N2	1.415 (2)
C14—C15	1.377 (4)	N2—C3	1.276 (3)
C14—H14	0.9500	C3—C31	1.461 (3)
C15—C16	1.387 (4)	C3—H3	0.9500
C15—H15	0.9500	C31—C32	1.389 (3)
C16—H16	0.9500	C31—C36	1.400 (3)
C1—O1	1.216 (3)	C32—C33	1.389 (3)
C1—C2	1.528 (3)	C32—H32	0.9500
C2—N1	1.288 (3)	C33—C34	1.377 (4)
C2—C21	1.476 (3)	C33—H33	0.9500
C21—C22	1.392 (3)	C34—C35	1.395 (4)
C21—C26	1.394 (3)	C34—H34	0.9500
C22—C23	1.390 (3)	C35—C36	1.382 (3)
C22—H22	0.9500	C35—H35	0.9500
C23—C24	1.377 (4)	C36—H36	0.9500
C16—C11—C12	119.5 (2)	C23—C24—C25	120.2 (2)
C16—C11—C1	121.1 (2)	C23—C24—H24	119.9
C12—C11—C1	119.4 (2)	C25—C24—H24	119.9
C13—C12—C11	119.7 (2)	C24—C25—C26	120.2 (2)
C13—C12—H12	120.1	C24—C25—H25	119.9
C11—C12—H12	120.1	C26—C25—H25	119.9
C12—C13—C14	120.3 (2)	C25—C26—C21	120.2 (2)
C12—C13—H13	119.9	C25—C26—H26	119.9
C14—C13—H13	119.9	C21—C26—H26	119.9
C15—C14—C13	120.4 (2)	C2—N1—N2	110.84 (16)
C15—C14—H14	119.8	C3—N2—N1	111.29 (17)
C13—C14—H14	119.8	N2—C3—C31	121.5 (2)
C14—C15—C16	119.8 (3)	N2—C3—H3	119.2
C14—C15—H15	120.1	C31—C3—H3	119.2
C16—C15—H15	120.1	C32—C31—C36	119.1 (2)
C15—C16—C11	120.2 (2)	C32—C31—C3	119.3 (2)
C15—C16—H16	119.9	C36—C31—C3	121.6 (2)
C11—C16—H16	119.9	C31—C32—C33	120.4 (2)
O1—C1—C11	122.96 (19)	C31—C32—H32	119.8
O1—C1—C2	117.85 (19)	C33—C32—H32	119.8
C11—C1—C2	119.19 (19)	C34—C33—C32	120.2 (2)
N1—C2—C21	120.24 (19)	C34—C33—H33	119.9
N1—C2—C1	120.61 (18)	C32—C33—H33	119.9
C21—C2—C1	118.91 (18)	C33—C34—C35	120.1 (2)
C22—C21—C26	118.99 (19)	C33—C34—H34	120.0
C22—C21—C2	120.9 (2)	C35—C34—H34	120.0
C26—C21—C2	120.1 (2)	C36—C35—C34	119.9 (2)
C23—C22—C21	120.4 (2)	C36—C35—H35	120.0
C23—C22—H22	119.8	C34—C35—H35	120.0
C21—C22—H22	119.8	C35—C36—C31	120.3 (2)
C24—C23—C22	120.0 (2)	C35—C36—H36	119.8
C24—C23—H23	120.0	C31—C36—H36	119.8
C22—C23—H23	120.0
C16—C11—C12—C13	0.7 (3)	C2—C21—C22—C23	−178.2 (2)
C1—C11—C12—C13	179.7 (2)	C21—C22—C23—C24	−0.4 (4)
C11—C12—C13—C14	0.2 (4)	C22—C23—C24—C25	−0.3 (4)
C12—C13—C14—C15	−1.0 (4)	C23—C24—C25—C26	0.8 (4)
C13—C14—C15—C16	0.7 (5)	C24—C25—C26—C21	−0.5 (4)
C14—C15—C16—C11	0.2 (4)	C22—C21—C26—C25	−0.2 (4)
C12—C11—C16—C15	−1.0 (3)	C2—C21—C26—C25	178.7 (2)
C1—C11—C16—C15	−179.9 (2)	C21—C2—N1—N2	−178.27 (18)
C16—C11—C1—O1	178.1 (2)	C1—C2—N1—N2	−3.8 (3)
C12—C11—C1—O1	−0.8 (3)	C2—N1—N2—C3	179.9 (2)
C16—C11—C1—C2	−2.4 (3)	N1—N2—C3—C31	176.64 (19)
C12—C11—C1—C2	178.7 (2)	N2—C3—C31—C32	−180.0 (2)
O1—C1—C2—N1	−100.0 (2)	N2—C3—C31—C36	−1.3 (3)
C11—C1—C2—N1	80.6 (3)	C36—C31—C32—C33	−1.4 (4)
O1—C1—C2—C21	74.6 (3)	C3—C31—C32—C33	177.3 (2)
C11—C1—C2—C21	−104.9 (2)	C31—C32—C33—C34	1.5 (4)
N1—C2—C21—C22	−176.3 (2)	C32—C33—C34—C35	−0.4 (4)
C1—C2—C21—C22	9.1 (3)	C33—C34—C35—C36	−0.7 (4)
N1—C2—C21—C26	4.9 (3)	C34—C35—C36—C31	0.7 (4)
C1—C2—C21—C26	−169.7 (2)	C32—C31—C36—C35	0.4 (4)
C26—C21—C22—C23	0.6 (4)	C3—C31—C36—C35	−178.3 (2)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C31–C36 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O1^i	0.95	2.61	3.337 (3)	134
C3—H3···O1^ii	0.95	2.41	3.272 (3)	151
C32—H32···O1^ii	0.95	2.68	3.478 (3)	141
C26—H26···Cg^iii	0.95	2.97	3.699 (3)	135

Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) x+1/4, y−1/4, −z+3/4; (iii) x+1/4, −y+1/4, z+1/4.