(E)-4-Nitro-2-[(phenyl­imino)­meth­yl]phenol

In the title compound, C₁₃H₁₀N₂O₃, the dihedral angle between the planes of the two aryl rings is 7.42 (10)°. An intra­molecular O—H...N hydrogen bond generates an S(6) ring. The crystal structure features C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.135
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C1      ..        6.4 s.u.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -8.701 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.480 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           3 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-4-Nitro-2-[(phenylimino)methyl]phenol

Crystal data

C13H10N2O3	F(000) = 504
Mr = 242.23	Dx = 1.412 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0774 (10) Å	Cell parameters from 3323 reflections
b = 6.5801 (6) Å	θ = 4.0–24.5°
c = 21.668 (3) Å	µ = 0.10 mm^−1
β = 98.240 (5)°	T = 296 K
V = 1139.8 (2) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1645 reflections with I > 2σ(I)
Radiation source: Sealed tube	Rint = 0.029
ω and φ scan	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→9
Tmin = 0.95, Tmax = 0.96	k = −8→8
15249 measured reflections	l = −28→28
2857 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.3112P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2857 reflections	Δρmax = 0.17 e Å^−3
164 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.2784 (2)	0.1044 (3)	−0.11963 (7)	0.0468 (4)
C2	0.1930 (3)	0.2130 (3)	−0.16876 (8)	0.0563 (5)
H2	0.179342	0.159614	−0.208907	0.068*
C3	0.1293 (3)	0.3986 (3)	−0.15790 (8)	0.0608 (5)
H3	0.072527	0.472297	−0.190992	0.073*
C4	0.1474 (2)	0.4797 (3)	−0.09835 (8)	0.0508 (5)
C5	0.2374 (2)	0.3697 (3)	−0.04848 (7)	0.0450 (4)
C6	0.3016 (2)	0.1809 (3)	−0.06025 (7)	0.0464 (4)
H6	0.360524	0.106126	−0.027877	0.056*
C7	0.2662 (2)	0.4542 (3)	0.01343 (8)	0.0506 (5)
H7	0.323271	0.377170	0.045658	0.061*
C8	0.2495 (2)	0.7204 (3)	0.08524 (8)	0.0464 (4)
C9	0.3526 (2)	0.6347 (3)	0.13497 (8)	0.0565 (5)
H9	0.403539	0.509943	0.130314	0.068*
C10	0.3796 (3)	0.7343 (3)	0.19118 (9)	0.0643 (6)
H10	0.449407	0.677035	0.224503	0.077*
C11	0.3043 (3)	0.9175 (4)	0.19849 (10)	0.0705 (6)
H11	0.322110	0.983561	0.236820	0.085*
C12	0.2030 (3)	1.0033 (3)	0.14949 (10)	0.0696 (6)
H12	0.151911	1.127794	0.154403	0.083*
C13	0.1768 (2)	0.9057 (3)	0.09319 (9)	0.0567 (5)
H13	0.108938	0.965574	0.059827	0.068*
N1	0.3522 (2)	−0.0902 (2)	−0.13139 (7)	0.0586 (4)
N2	0.21561 (19)	0.6317 (2)	0.02536 (6)	0.0486 (4)
O1	0.3253 (2)	−0.1609 (2)	−0.18406 (7)	0.0843 (5)
O2	0.4381 (2)	−0.1762 (2)	−0.08827 (7)	0.0723 (5)
O3	0.08189 (19)	0.6599 (2)	−0.08898 (6)	0.0665 (4)
H3A	0.106727	0.692303	−0.052274	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0517 (11)	0.0475 (10)	0.0416 (9)	−0.0074 (8)	0.0083 (8)	0.0025 (7)
C2	0.0634 (13)	0.0679 (13)	0.0357 (9)	−0.0131 (10)	0.0005 (8)	0.0027 (8)
C3	0.0643 (13)	0.0672 (13)	0.0456 (10)	−0.0038 (10)	−0.0102 (9)	0.0162 (9)
C4	0.0474 (11)	0.0519 (11)	0.0518 (10)	−0.0024 (9)	0.0028 (8)	0.0111 (8)
C5	0.0453 (10)	0.0492 (10)	0.0396 (9)	−0.0041 (8)	0.0027 (7)	0.0052 (7)
C6	0.0494 (11)	0.0506 (10)	0.0378 (9)	−0.0009 (8)	0.0009 (7)	0.0072 (7)
C7	0.0540 (12)	0.0545 (11)	0.0422 (9)	0.0021 (9)	0.0032 (8)	0.0063 (8)
C8	0.0416 (10)	0.0518 (10)	0.0465 (9)	−0.0046 (8)	0.0091 (8)	0.0000 (8)
C9	0.0554 (12)	0.0619 (12)	0.0525 (11)	0.0060 (9)	0.0087 (9)	−0.0016 (9)
C10	0.0556 (13)	0.0841 (15)	0.0515 (11)	0.0048 (11)	0.0018 (9)	−0.0030 (10)
C11	0.0585 (14)	0.0892 (16)	0.0627 (13)	−0.0009 (12)	0.0048 (10)	−0.0242 (11)
C12	0.0649 (15)	0.0666 (13)	0.0758 (14)	0.0072 (11)	0.0056 (11)	−0.0184 (11)
C13	0.0511 (12)	0.0586 (12)	0.0590 (11)	0.0041 (9)	0.0029 (9)	−0.0009 (9)
N1	0.0688 (12)	0.0590 (10)	0.0495 (9)	−0.0078 (9)	0.0134 (8)	−0.0047 (8)
N2	0.0477 (9)	0.0506 (9)	0.0483 (8)	−0.0002 (7)	0.0091 (7)	0.0006 (7)
O1	0.1271 (16)	0.0753 (10)	0.0519 (8)	−0.0080 (9)	0.0177 (9)	−0.0165 (7)
O2	0.0777 (11)	0.0665 (9)	0.0702 (10)	0.0142 (8)	0.0022 (8)	−0.0039 (7)
O3	0.0689 (10)	0.0614 (9)	0.0662 (9)	0.0136 (7)	−0.0008 (7)	0.0115 (7)

Geometric parameters (Å, º)

C1—C6	1.369 (2)	C8—C9	1.384 (2)
C1—C2	1.382 (2)	C8—N2	1.413 (2)
C1—N1	1.450 (2)	C9—C10	1.373 (3)
C2—C3	1.359 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.370 (3)
C3—C4	1.385 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.366 (3)
C4—O3	1.326 (2)	C11—H11	0.9300
C4—C5	1.412 (2)	C12—C13	1.368 (3)
C5—C6	1.384 (2)	C12—H12	0.9300
C5—C7	1.440 (2)	C13—H13	0.9300
C6—H6	0.9300	N1—O2	1.220 (2)
C7—N2	1.276 (2)	N1—O1	1.2228 (19)
C7—H7	0.9300	O3—H3A	0.8200
C8—C13	1.375 (3)
C6—C1—C2	121.32 (17)	C13—C8—N2	116.85 (16)
C6—C1—N1	119.04 (15)	C9—C8—N2	124.19 (16)
C2—C1—N1	119.58 (16)	C10—C9—C8	119.81 (19)
C3—C2—C1	119.42 (17)	C10—C9—H9	120.1
C3—C2—H2	120.3	C8—C9—H9	120.1
C1—C2—H2	120.3	C11—C10—C9	120.4 (2)
C2—C3—C4	121.04 (17)	C11—C10—H10	119.8
C2—C3—H3	119.5	C9—C10—H10	119.8
C4—C3—H3	119.5	C12—C11—C10	120.01 (19)
O3—C4—C3	119.74 (16)	C12—C11—H11	120.0
O3—C4—C5	120.94 (16)	C10—C11—H11	120.0
C3—C4—C5	119.31 (17)	C11—C12—C13	119.9 (2)
C6—C5—C4	118.98 (15)	C11—C12—H12	120.1
C6—C5—C7	120.24 (15)	C13—C12—H12	120.1
C4—C5—C7	120.76 (16)	C12—C13—C8	120.93 (19)
C1—C6—C5	119.92 (16)	C12—C13—H13	119.5
C1—C6—H6	120.0	C8—C13—H13	119.5
C5—C6—H6	120.0	O2—N1—O1	122.93 (18)
N2—C7—C5	121.91 (16)	O2—N1—C1	118.55 (15)
N2—C7—H7	119.0	O1—N1—C1	118.52 (17)
C5—C7—H7	119.0	C7—N2—C8	122.60 (15)
C13—C8—C9	118.95 (17)	C4—O3—H3A	109.5
C6—C1—C2—C3	−0.7 (3)	C13—C8—C9—C10	0.5 (3)
N1—C1—C2—C3	−177.65 (18)	N2—C8—C9—C10	179.08 (18)
C1—C2—C3—C4	−0.5 (3)	C8—C9—C10—C11	0.4 (3)
C2—C3—C4—O3	−179.07 (19)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	1.6 (3)	C10—C11—C12—C13	0.1 (3)
O3—C4—C5—C6	179.13 (17)	C11—C12—C13—C8	0.8 (3)
C3—C4—C5—C6	−1.6 (3)	C9—C8—C13—C12	−1.1 (3)
O3—C4—C5—C7	−2.6 (3)	N2—C8—C13—C12	−179.80 (18)
C3—C4—C5—C7	176.72 (17)	C6—C1—N1—O2	−2.7 (3)
C2—C1—C6—C5	0.7 (3)	C2—C1—N1—O2	174.36 (17)
N1—C1—C6—C5	177.68 (16)	C6—C1—N1—O1	177.16 (17)
C4—C5—C6—C1	0.4 (3)	C2—C1—N1—O1	−5.8 (3)
C7—C5—C6—C1	−177.87 (16)	C5—C7—N2—C8	−177.03 (16)
C6—C5—C7—N2	176.63 (17)	C13—C8—N2—C7	−174.99 (17)
C4—C5—C7—N2	−1.7 (3)	C9—C8—N2—C7	6.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.93	2.60	3.278 (2)	130
C7—H7···O2^ii	0.93	2.41	3.252 (2)	150
O3—H3A···N2	0.82	1.83	2.5637 (19)	149

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