2-{(Z)-2-[(E)-1-(2-Hydroxy­phen­yl)methyl­idene]hydrazono}-1,2-diphenyl­ethan-1-one

The title compound, C₂₁H₁₅N₂O₂, contains two benzene rings (the phenolic ring and the nearest benzene ring) connected through an azine group that show a little deviation from coplanarity. There is an intra­molecular hydrogen bond involving the phenol hydroxyl group and the nearest N atom in the azine chain [O—H...N = 2.608 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.125
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C21     ..       5.03 su

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

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS Software (Stoe & Cie, 1997); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: IPDS Software; software used to prepare material for publication: SHELXL97.

2-{(Z)-2-[(E)-1-(2-Hydroxyphenyl)methylidene]hydrazono}-1,2-diphenylethan-1-one

Crystal data

C21H16N2O2	F(000) = 688
Mr = 328.36	Dx = 1.261 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13138 reflections
a = 16.804 (3) Å	θ = 2.1–26.1°
b = 9.2783 (13) Å	µ = 0.08 mm^−1
c = 11.244 (2) Å	T = 290 K
β = 99.39 (2)°	Needle, light yellow
V = 1729.7 (5) Å^3	0.5 × 0.2 × 0.1 mm
Z = 4

Data collection

Stoe IPDS area-detector diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	1833 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 6.67 pixels mm^-1	θmax = 26.1°, θmin = 2.5°
φ scans	h = −20→20
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	k = −11→10
Tmin = 0.953, Tmax = 0.992	l = −13→13
13138 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0708P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
3356 reflections	Δρmax = 0.12 e Å^−3
235 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (4)

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	0.37290 (9)	0.50610 (15)	0.12894 (12)	0.0768 (4)
H1	0.3182 (18)	0.533 (3)	0.104 (2)	0.129 (9)*
O2	0.18521 (9)	0.58128 (16)	−0.15861 (12)	0.0866 (5)
N1	0.14011 (8)	0.57944 (17)	0.10801 (14)	0.0699 (4)
N2	0.21814 (8)	0.51908 (16)	0.13160 (13)	0.0655 (4)
C1	0.19183 (10)	0.66049 (19)	−0.07127 (15)	0.0604 (4)
C2	0.25871 (9)	0.76367 (17)	−0.04074 (13)	0.0531 (4)
C3	0.26016 (11)	0.86075 (19)	0.05299 (16)	0.0636 (5)
H3	0.2186	0.8607	0.0984	0.076*
C4	0.32255 (13)	0.9572 (2)	0.07945 (18)	0.0770 (5)
H4	0.3226	1.0234	0.1416	0.092*
C5	0.38455 (12)	0.9562 (2)	0.0147 (2)	0.0796 (6)
H5	0.4268	1.0214	0.0329	0.095*
C6	0.38469 (12)	0.8597 (2)	−0.07652 (19)	0.0773 (6)
H6	0.4275	0.8588	−0.1195	0.093*
C7	0.32225 (11)	0.7637 (2)	−0.10575 (16)	0.0671 (5)
H7	0.3226	0.6990	−0.1688	0.080*
C8	0.12814 (10)	0.65259 (19)	0.00958 (16)	0.0606 (4)
C9	0.05066 (10)	0.7265 (2)	−0.02809 (16)	0.0649 (5)
C10	0.04072 (13)	0.8245 (2)	−0.12152 (19)	0.0832 (6)
H10	0.0832	0.8420	−0.1632	0.100*
C11	−0.03132 (16)	0.8970 (3)	−0.1542 (2)	0.1014 (8)
H11	−0.0366	0.9642	−0.2163	0.122*
C12	−0.09430 (16)	0.8706 (3)	−0.0962 (3)	0.1080 (9)
H12	−0.1430	0.9185	−0.1191	0.130*
C13	−0.08601 (14)	0.7727 (3)	−0.0034 (3)	0.1083 (9)
H13	−0.1292	0.7550	0.0367	0.130*
C14	−0.01387 (12)	0.6999 (3)	0.0310 (2)	0.0876 (6)
H14	−0.0089	0.6334	0.0936	0.105*
C15	0.22684 (12)	0.4204 (2)	0.21183 (17)	0.0657 (5)
H15	0.1815 (12)	0.388 (2)	0.2536 (17)	0.080 (6)*
C16	0.30362 (11)	0.34911 (19)	0.24873 (15)	0.0618 (4)
C17	0.37343 (11)	0.3939 (2)	0.20630 (15)	0.0643 (5)
C18	0.44612 (12)	0.3254 (2)	0.24514 (19)	0.0807 (6)
H18	0.4922	0.3548	0.2158	0.097*
C19	0.45078 (16)	0.2147 (3)	0.3265 (2)	0.0906 (7)
H19	0.5001	0.1702	0.3528	0.109*
C20	0.38344 (17)	0.1689 (2)	0.36933 (19)	0.0903 (7)
H20	0.3869	0.0929	0.4239	0.108*
C21	0.31036 (14)	0.2358 (2)	0.33125 (17)	0.0796 (6)
H21	0.2648	0.2048	0.3612	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0639 (8)	0.0825 (10)	0.0851 (9)	0.0029 (7)	0.0158 (7)	0.0166 (7)
O2	0.0854 (10)	0.0927 (11)	0.0807 (9)	−0.0063 (8)	0.0107 (7)	−0.0307 (8)
N1	0.0512 (8)	0.0732 (11)	0.0854 (10)	−0.0008 (7)	0.0116 (7)	0.0090 (8)
N2	0.0529 (8)	0.0679 (10)	0.0752 (9)	0.0019 (7)	0.0092 (7)	0.0093 (8)
C1	0.0592 (10)	0.0615 (11)	0.0591 (10)	0.0058 (8)	0.0051 (8)	−0.0041 (8)
C2	0.0515 (9)	0.0556 (10)	0.0517 (8)	0.0046 (7)	0.0071 (7)	0.0030 (7)
C3	0.0609 (10)	0.0638 (11)	0.0677 (10)	−0.0018 (8)	0.0154 (8)	−0.0057 (9)
C4	0.0790 (13)	0.0707 (13)	0.0802 (12)	−0.0091 (10)	0.0097 (10)	−0.0126 (10)
C5	0.0629 (12)	0.0791 (14)	0.0946 (14)	−0.0128 (10)	0.0068 (10)	0.0110 (12)
C6	0.0609 (11)	0.0905 (15)	0.0842 (13)	−0.0021 (11)	0.0226 (10)	0.0174 (12)
C7	0.0682 (11)	0.0755 (13)	0.0599 (10)	0.0089 (10)	0.0176 (8)	0.0038 (9)
C8	0.0529 (10)	0.0581 (11)	0.0693 (11)	−0.0031 (8)	0.0058 (8)	−0.0027 (8)
C9	0.0524 (10)	0.0655 (12)	0.0746 (11)	0.0016 (8)	0.0035 (8)	−0.0097 (9)
C10	0.0753 (13)	0.0863 (15)	0.0843 (13)	0.0159 (11)	0.0015 (10)	0.0040 (11)
C11	0.0993 (19)	0.0972 (18)	0.0985 (16)	0.0339 (14)	−0.0111 (14)	−0.0038 (13)
C12	0.0785 (17)	0.112 (2)	0.124 (2)	0.0314 (15)	−0.0128 (15)	−0.0372 (17)
C13	0.0605 (14)	0.131 (2)	0.134 (2)	0.0106 (14)	0.0183 (14)	−0.0318 (19)
C14	0.0586 (12)	0.1004 (16)	0.1046 (16)	0.0025 (11)	0.0160 (11)	−0.0063 (12)
C15	0.0666 (11)	0.0647 (12)	0.0664 (10)	−0.0048 (9)	0.0132 (9)	0.0038 (9)
C16	0.0695 (11)	0.0573 (11)	0.0566 (9)	0.0011 (8)	0.0047 (8)	0.0005 (8)
C17	0.0662 (11)	0.0640 (12)	0.0607 (10)	0.0047 (9)	0.0044 (8)	−0.0036 (9)
C18	0.0684 (13)	0.0820 (15)	0.0879 (14)	0.0135 (10)	0.0015 (10)	−0.0057 (11)
C19	0.0948 (17)	0.0800 (15)	0.0876 (15)	0.0258 (13)	−0.0130 (12)	−0.0088 (12)
C20	0.124 (2)	0.0673 (14)	0.0730 (13)	0.0180 (14)	−0.0030 (13)	0.0060 (10)
C21	0.0983 (16)	0.0692 (13)	0.0711 (12)	0.0020 (11)	0.0134 (11)	0.0048 (10)

Geometric parameters (Å, º)

O1—C17	1.356 (2)	C10—C11	1.381 (3)
O1—H1	0.95 (3)	C10—H10	0.9300
O2—C1	1.217 (2)	C11—C12	1.353 (4)
N1—C8	1.286 (2)	C11—H11	0.9300
N1—N2	1.411 (2)	C12—C13	1.373 (4)
N2—C15	1.277 (2)	C12—H12	0.9300
C1—C2	1.473 (2)	C13—C14	1.386 (3)
C1—C8	1.515 (2)	C13—H13	0.9300
C2—C3	1.384 (2)	C14—H14	0.9300
C2—C7	1.389 (2)	C15—C16	1.449 (3)
C3—C4	1.374 (3)	C15—H15	1.00 (2)
C3—H3	0.9300	C16—C21	1.394 (3)
C4—C5	1.365 (3)	C16—C17	1.400 (2)
C4—H4	0.9300	C17—C18	1.383 (3)
C5—C6	1.361 (3)	C18—C19	1.369 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.375 (3)	C19—C20	1.368 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.380 (3)
C8—C9	1.471 (2)	C20—H20	0.9300
C9—C10	1.379 (3)	C21—H21	0.9300
C9—C14	1.383 (3)
C17—O1—H1	107.1 (16)	C12—C11—C10	120.3 (3)
C8—N1—N2	112.42 (14)	C12—C11—H11	119.9
C15—N2—N1	114.41 (15)	C10—C11—H11	119.9
O2—C1—C2	123.10 (16)	C11—C12—C13	119.7 (2)
O2—C1—C8	118.32 (16)	C11—C12—H12	120.1
C2—C1—C8	118.58 (14)	C13—C12—H12	120.1
C3—C2—C7	118.77 (16)	C12—C13—C14	120.6 (2)
C3—C2—C1	121.23 (15)	C12—C13—H13	119.7
C7—C2—C1	120.00 (15)	C14—C13—H13	119.7
C4—C3—C2	120.48 (17)	C9—C14—C13	119.9 (2)
C4—C3—H3	119.8	C9—C14—H14	120.1
C2—C3—H3	119.8	C13—C14—H14	120.1
C5—C4—C3	120.10 (19)	N2—C15—C16	121.57 (18)
C5—C4—H4	120.0	N2—C15—H15	122.5 (11)
C3—C4—H4	120.0	C16—C15—H15	116.0 (11)
C6—C5—C4	120.14 (19)	C21—C16—C17	117.98 (17)
C6—C5—H5	119.9	C21—C16—C15	120.42 (18)
C4—C5—H5	119.9	C17—C16—C15	121.56 (16)
C5—C6—C7	120.73 (18)	O1—C17—C18	117.94 (18)
C5—C6—H6	119.6	O1—C17—C16	121.92 (16)
C7—C6—H6	119.6	C18—C17—C16	120.13 (18)
C6—C7—C2	119.77 (17)	C19—C18—C17	120.5 (2)
C6—C7—H7	120.1	C19—C18—H18	119.8
C2—C7—H7	120.1	C17—C18—H18	119.8
N1—C8—C9	120.04 (16)	C20—C19—C18	120.5 (2)
N1—C8—C1	121.03 (15)	C20—C19—H19	119.7
C9—C8—C1	118.90 (16)	C18—C19—H19	119.7
C10—C9—C14	118.45 (19)	C19—C20—C21	119.7 (2)
C10—C9—C8	121.22 (17)	C19—C20—H20	120.1
C14—C9—C8	120.33 (18)	C21—C20—H20	120.1
C9—C10—C11	121.0 (2)	C20—C21—C16	121.1 (2)
C9—C10—H10	119.5	C20—C21—H21	119.4
C11—C10—H10	119.5	C16—C21—H21	119.4
C8—N1—N2—C15	−164.91 (16)	C14—C9—C10—C11	1.3 (3)
O2—C1—C2—C3	174.12 (17)	C8—C9—C10—C11	−177.96 (18)
C8—C1—C2—C3	−5.8 (2)	C9—C10—C11—C12	−1.4 (3)
O2—C1—C2—C7	−6.5 (3)	C10—C11—C12—C13	0.9 (4)
C8—C1—C2—C7	173.58 (15)	C11—C12—C13—C14	−0.4 (4)
C7—C2—C3—C4	1.3 (3)	C10—C9—C14—C13	−0.8 (3)
C1—C2—C3—C4	−179.32 (16)	C8—C9—C14—C13	178.50 (19)
C2—C3—C4—C5	−1.2 (3)	C12—C13—C14—C9	0.4 (4)
C3—C4—C5—C6	0.1 (3)	N1—N2—C15—C16	−178.71 (15)
C4—C5—C6—C7	0.9 (3)	N2—C15—C16—C21	−176.16 (17)
C5—C6—C7—C2	−0.8 (3)	N2—C15—C16—C17	5.9 (3)
C3—C2—C7—C6	−0.3 (2)	C21—C16—C17—O1	−177.87 (17)
C1—C2—C7—C6	−179.69 (16)	C15—C16—C17—O1	0.1 (3)
N2—N1—C8—C9	−178.49 (14)	C21—C16—C17—C18	0.7 (3)
N2—N1—C8—C1	3.5 (2)	C15—C16—C17—C18	178.71 (17)
O2—C1—C8—N1	98.5 (2)	O1—C17—C18—C19	177.77 (18)
C2—C1—C8—N1	−81.6 (2)	C16—C17—C18—C19	−0.9 (3)
O2—C1—C8—C9	−79.5 (2)	C17—C18—C19—C20	0.8 (3)
C2—C1—C8—C9	100.37 (19)	C18—C19—C20—C21	−0.7 (3)
N1—C8—C9—C10	169.10 (18)	C19—C20—C21—C16	0.5 (3)
C1—C8—C9—C10	−12.8 (3)	C17—C16—C21—C20	−0.5 (3)
N1—C8—C9—C14	−10.2 (3)	C15—C16—C21—C20	−178.57 (18)
C1—C8—C9—C14	167.89 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.95 (3)	1.76 (3)	2.608 (2)	147 (2)