Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitro­phen­yl)diazen-1-yl]naphthalen-2-ol

The hydrazone form is the predominant form in the solid state. The naphthol and benzene fragments attached to the –N=N– moiety adopt the s-trans conformation. There are only two types of inter­molecular inter­actions in the crystal structure: strong hydrogen-bonding C—H...O inter­actions and π–π stacking inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.041
• wR factor = 0.087
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
REFI020_ALERT_1_A  _refine_ls_extinction_coef is missing
            Extinction coefficient applied in corrections.

Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -2.400
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        48% Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00582 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.208 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H9       ..O3       .       2.62 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       1.10 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

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

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

# start Validation Reply Form
_vrf_REFI020_I
;
PROBLEM: _refine_ls_extinction_coef is missing
RESPONSE: ...
;
# end Validation Reply Form 

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Reference check results

The following references were not checked in detail as they were not recognized as references to journal articles

Antonov, L. (2016). Tautomerism: concepts and applications in science and technology Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA.

Bruker (2012). APEX2 (Version 2012.10-0), SAINT (version 8.27B), SADABS (version 2012/1), BrukerAXS Inc, Madison, Wisconsin, USA. [software reference?]

Christie, R. M. (2001). Colour chemistry Cambridge, UK: Royal Society of Chemistry.

Chudgar, R. J. & Oakes, J. (2003). Vol. Kirk-Othmer Encyclopedia of Chemical Technology, edited by John Wiley & Sons, Inc. p. 01261503082104.a01.pub2. Hoboken, NJ, USA: John Wiley & Sons, Inc. [book reference?]

Hunger, K. (2003). Industrial dyes: chemistry, properties, applications Weinheim: Wiley-VCH.

The following references may be incorrectly formatted

Benkhaya, S., M'rabet, S. & El Harfi, A. (2020). Heliyon. 6, e03271--e03296.
[Unrecognized journal title.]

Ran, J., Pryazhnikova, V. G. & Telegin, F. Y. (2022). Colorants. 1, 280--297.
[Unrecognized journal title.]

Shi, J. & Chen, L. (2014). Anal. Methods. 6, 8129--8135.
[Unrecognized journal title.]

All references appear to be cited unambiguously

Citation comments

2 dates found in data_global _publ_body_contents that could be part of a citation but not found in reference list: 2022, 2022

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

(1E)-1-[2-(3-Nitrophenyl)hydrazin-1-ylidene]-1,2-dihydronaphthalen-2-one

Crystal data

C16H11N3O3	F(000) = 608
Mr = 293.28	Dx = 1.433 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1342 reflections
a = 6.0981 (9) Å	θ = 2.7–18.9°
b = 14.485 (2) Å	µ = 0.10 mm^−1
c = 15.389 (2) Å	T = 296 K
V = 1359.3 (3) Å^3	Needle, red
Z = 4	0.50 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	1342 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.113
Graphite monochromator	θmax = 26.4°, θmin = 2.7°
phi and ω scans	h = −7→7
12470 measured reflections	k = −18→18
2803 independent reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	W = 1/[Σ^2(FO^2) + (0.0223P)^2] WHERE P = (FO^2 + 2FC^2)/3
wR(F^2) = 0.087	(Δ/σ)max < 0.001
S = 0.81	Δρmax = 0.12 e Å^−3
2803 reflections	Δρmin = −0.13 e Å^−3
203 parameters	Extinction correction: shelxl
1 restraint	Absolute structure: Flack (1983), 5026 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −2.4 (10)
Secondary atom site location: difference Fourier map

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.1440 (4)	0.7501 (2)	0.56438 (19)	0.0628 (11)
O2	1.2087 (6)	0.4813 (3)	0.5013 (2)	0.0970 (16)
O3	0.9538 (5)	0.5490 (2)	0.4279 (2)	0.0808 (11)
N1	0.3939 (5)	0.6367 (2)	0.6436 (2)	0.0463 (12)
N2	0.2663 (5)	0.6417 (2)	0.7121 (2)	0.0428 (11)
N3	1.0269 (7)	0.5166 (3)	0.4945 (3)	0.0623 (17)
C1	0.5740 (6)	0.5775 (3)	0.6452 (2)	0.0403 (12)
C2	0.7054 (6)	0.5749 (2)	0.5720 (2)	0.0437 (12)
C3	0.8870 (6)	0.5181 (3)	0.5725 (3)	0.0457 (12)
C4	0.9420 (6)	0.4646 (3)	0.6429 (3)	0.0597 (17)
C5	0.8071 (7)	0.4677 (3)	0.7151 (3)	0.0603 (17)
C6	0.6243 (6)	0.5242 (3)	0.7173 (3)	0.0490 (14)
C7	0.0931 (6)	0.6974 (3)	0.7091 (3)	0.0397 (12)
C8	0.0303 (6)	0.7519 (3)	0.6340 (3)	0.0480 (16)
C9	−0.1635 (6)	0.8064 (3)	0.6396 (3)	0.0583 (17)
C10	−0.2879 (7)	0.8059 (3)	0.7116 (3)	0.0567 (16)
C11	−0.2361 (6)	0.7522 (3)	0.7869 (3)	0.0470 (14)
C12	−0.0426 (6)	0.6988 (3)	0.7871 (3)	0.0417 (12)
C13	0.0082 (6)	0.6472 (3)	0.8611 (3)	0.0503 (16)
C14	−0.1283 (7)	0.6474 (3)	0.9321 (3)	0.0580 (17)
C15	−0.3181 (7)	0.6989 (3)	0.9312 (3)	0.0627 (17)
C16	−0.3733 (7)	0.7510 (3)	0.8599 (3)	0.0623 (17)
H1	0.357 (6)	0.667 (2)	0.5978 (18)	0.063 (15)*
H2	0.67210	0.61060	0.52350	0.0530*
H4	1.06630	0.42750	0.64210	0.0720*
H5	0.83990	0.43110	0.76300	0.0720*
H6	0.53620	0.52640	0.76660	0.0590*
H9	−0.20470	0.84290	0.59260	0.0700*
H10	−0.41370	0.84220	0.71260	0.0680*
H13	0.13610	0.61220	0.86230	0.0600*
H14	−0.09250	0.61260	0.98090	0.0700*
H15	−0.40990	0.69840	0.97940	0.0750*
H16	−0.50180	0.78550	0.86010	0.0750*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0707 (19)	0.0686 (19)	0.0491 (18)	0.0118 (17)	0.0061 (17)	0.0121 (18)
O2	0.059 (2)	0.125 (3)	0.107 (3)	0.023 (2)	0.021 (2)	−0.022 (2)
O3	0.093 (2)	0.095 (2)	0.0545 (19)	−0.014 (2)	0.019 (2)	−0.002 (2)
N1	0.047 (2)	0.054 (2)	0.038 (2)	0.0038 (18)	−0.0002 (19)	0.0050 (19)
N2	0.0433 (19)	0.0452 (19)	0.0399 (18)	0.0002 (17)	0.0032 (17)	−0.0004 (17)
N3	0.062 (3)	0.065 (3)	0.060 (3)	−0.012 (2)	0.016 (3)	−0.018 (2)
C1	0.039 (2)	0.043 (2)	0.039 (2)	−0.0021 (19)	−0.002 (2)	0.000 (2)
C2	0.047 (2)	0.042 (2)	0.042 (2)	−0.006 (2)	0.000 (2)	0.002 (2)
C3	0.046 (2)	0.046 (2)	0.045 (2)	−0.004 (2)	0.004 (2)	−0.006 (2)
C4	0.052 (3)	0.053 (3)	0.074 (3)	0.006 (2)	0.003 (3)	0.000 (3)
C5	0.064 (3)	0.054 (3)	0.063 (3)	0.009 (2)	0.002 (3)	0.019 (3)
C6	0.051 (2)	0.053 (3)	0.043 (2)	0.000 (2)	0.003 (2)	0.005 (2)
C7	0.041 (2)	0.037 (2)	0.041 (2)	0.000 (2)	−0.001 (2)	−0.004 (2)
C8	0.051 (3)	0.044 (2)	0.049 (3)	0.005 (2)	−0.004 (2)	0.004 (2)
C9	0.064 (3)	0.049 (3)	0.062 (3)	0.011 (2)	−0.006 (3)	0.008 (2)
C10	0.057 (3)	0.047 (2)	0.066 (3)	0.007 (2)	−0.005 (3)	−0.004 (3)
C11	0.043 (2)	0.043 (2)	0.055 (3)	−0.004 (2)	−0.001 (2)	−0.009 (3)
C12	0.042 (2)	0.042 (2)	0.041 (2)	−0.003 (2)	−0.008 (2)	−0.004 (2)
C13	0.050 (3)	0.055 (3)	0.046 (2)	0.000 (2)	−0.002 (2)	−0.003 (2)
C14	0.062 (3)	0.067 (3)	0.045 (3)	−0.001 (3)	0.003 (2)	−0.002 (3)
C15	0.058 (3)	0.071 (3)	0.059 (3)	0.000 (3)	0.015 (3)	−0.010 (3)
C16	0.057 (3)	0.058 (3)	0.072 (3)	0.005 (3)	0.010 (3)	−0.010 (3)

Geometric parameters (Å, º)

O1—C8	1.276 (5)	C10—C11	1.431 (6)
O2—N3	1.225 (6)	C11—C16	1.401 (6)
O3—N3	1.212 (5)	C11—C12	1.411 (5)
N1—N2	1.312 (4)	C12—C13	1.397 (6)
N1—C1	1.394 (5)	C13—C14	1.374 (6)
N2—C7	1.330 (5)	C14—C15	1.377 (6)
N3—C3	1.473 (6)	C15—C16	1.374 (6)
C1—C2	1.383 (5)	C2—H2	0.9300
C1—C6	1.386 (6)	C4—H4	0.9300
N1—H1	0.86 (3)	C5—H5	0.9300
C2—C3	1.380 (5)	C6—H6	0.9300
C3—C4	1.374 (6)	C9—H9	0.9300
C4—C5	1.383 (6)	C10—H10	0.9300
C5—C6	1.383 (6)	C13—H13	0.9300
C7—C8	1.451 (6)	C14—H14	0.9300
C7—C12	1.458 (6)	C15—H15	0.9300
C8—C9	1.424 (5)	C16—H16	0.9300
C9—C10	1.343 (6)
N2—N1—C1	119.2 (3)	C11—C12—C13	118.7 (4)
N1—N2—C7	118.5 (3)	C7—C12—C11	118.7 (4)
O2—N3—O3	124.5 (4)	C7—C12—C13	122.5 (4)
O2—N3—C3	117.4 (4)	C12—C13—C14	120.9 (4)
O3—N3—C3	118.1 (4)	C13—C14—C15	120.2 (4)
N1—C1—C2	117.3 (3)	C14—C15—C16	120.8 (4)
N1—C1—C6	122.1 (3)	C11—C16—C15	120.1 (4)
C2—C1—C6	120.6 (4)	C1—C2—H2	121.00
N2—N1—H1	118 (2)	C3—C2—H2	121.00
C1—N1—H1	122 (2)	C3—C4—H4	121.00
C1—C2—C3	118.5 (3)	C5—C4—H4	121.00
N3—C3—C4	119.5 (4)	C4—C5—H5	119.00
N3—C3—C2	118.0 (4)	C6—C5—H5	119.00
C2—C3—C4	122.5 (4)	C1—C6—H6	120.00
C3—C4—C5	118.0 (4)	C5—C6—H6	120.00
C4—C5—C6	121.2 (4)	C8—C9—H9	119.00
C1—C6—C5	119.2 (4)	C10—C9—H9	119.00
C8—C7—C12	119.9 (3)	C9—C10—H10	118.00
N2—C7—C8	124.6 (4)	C11—C10—H10	118.00
N2—C7—C12	115.5 (4)	C12—C13—H13	120.00
C7—C8—C9	118.2 (4)	C14—C13—H13	120.00
O1—C8—C9	120.9 (4)	C13—C14—H14	120.00
O1—C8—C7	120.9 (3)	C15—C14—H14	120.00
C8—C9—C10	121.1 (4)	C14—C15—H15	120.00
C9—C10—C11	123.1 (4)	C16—C15—H15	120.00
C12—C11—C16	119.4 (4)	C11—C16—H16	120.00
C10—C11—C12	119.0 (4)	C15—C16—H16	120.00
C10—C11—C16	121.6 (4)
C1—N1—N2—C7	−179.0 (3)	C12—C7—C8—C9	0.7 (6)
N2—N1—C1—C2	−179.4 (3)	N2—C7—C12—C11	−176.4 (4)
N2—N1—C1—C6	−0.7 (5)	N2—C7—C12—C13	1.7 (6)
N1—N2—C7—C8	1.8 (6)	C8—C7—C12—C11	1.3 (6)
N1—N2—C7—C12	179.4 (3)	C8—C7—C12—C13	179.4 (4)
O2—N3—C3—C2	165.7 (4)	O1—C8—C9—C10	177.6 (4)
O2—N3—C3—C4	−13.5 (6)	C7—C8—C9—C10	−1.5 (6)
O3—N3—C3—C2	−15.4 (6)	C8—C9—C10—C11	0.4 (7)
O3—N3—C3—C4	165.5 (4)	C9—C10—C11—C12	1.7 (7)
N1—C1—C2—C3	178.9 (3)	C9—C10—C11—C16	−177.9 (4)
C6—C1—C2—C3	0.0 (6)	C10—C11—C12—C7	−2.5 (6)
N1—C1—C6—C5	−179.2 (4)	C10—C11—C12—C13	179.4 (4)
C2—C1—C6—C5	−0.4 (6)	C16—C11—C12—C7	177.2 (4)
C1—C2—C3—N3	−179.4 (4)	C16—C11—C12—C13	−1.0 (6)
C1—C2—C3—C4	−0.3 (6)	C10—C11—C16—C15	−179.8 (4)
N3—C3—C4—C5	180.0 (4)	C12—C11—C16—C15	0.6 (6)
C2—C3—C4—C5	0.8 (6)	C7—C12—C13—C14	−177.4 (4)
C3—C4—C5—C6	−1.2 (6)	C11—C12—C13—C14	0.7 (6)
C4—C5—C6—C1	1.0 (6)	C12—C13—C14—C15	−0.1 (7)
N2—C7—C8—O1	−0.9 (6)	C13—C14—C15—C16	−0.3 (7)
N2—C7—C8—C9	178.2 (4)	C14—C15—C16—C11	0.0 (7)
C12—C7—C8—O1	−178.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (3)	1.84 (3)	2.551 (4)	138 (3)
C2—H2···O1^i	0.93	2.43	3.312 (4)	157
C9—H9···O3^ii	0.93	2.62	3.303 (5)	130

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