(E)-1-[2-(3,4-Di­methyl­phen­yl)diazen-2-ium-1-yl]naphthalen-2-olate

Chetioui, S.; Boutebdja, M.; Boudraa, M.; Touzani, R.; Merazig, H.

doi:10.1107/S2414314617002590

(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

S. Chetioui, M. Boutebdja, M. Boudraa, R. Touzani and H. Merazig

The title zwitterion, C₁₈H₁₆N₂O, features an intramolecular N—H

O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H

O interactions are also observed.

Keywords: crystal structure; zwitterion; azo dyes; hydrogen bonding; π–π stacking.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617002590/hb4118sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314617002590/hb4118Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617002590/hb4118Isup3.cml Supplementary material

CCDC reference: 1532675

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.044
wR factor = 0.121
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     --  C4      ..        6.0 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.821 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of >C11A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C12A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C13A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C14A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C15A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C16A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C17A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C18A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C11B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C12B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C13B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C14B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C15B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C16B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C17B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C18B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H12A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H13A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H16A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H17A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H17B   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H17C   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H18A   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H18B   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >H18C   is Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H12B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H13B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H16B   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H17D   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H17E   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H17F   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H18D   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H18E   is Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <H18F   is Constrained at       0.25 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         38 % Note
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5     -C10           1.42 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Note

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

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

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate top

Crystal data top

C₁₈H₁₆N₂O	F(000) = 584
M_r = 276.33	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3155 reflections
a = 11.6326 (5) Å	θ = 2.5–28.1°
b = 6.1866 (2) Å	µ = 0.08 mm⁻¹
c = 20.1712 (8) Å	T = 173 K
β = 98.023 (2)°	Prism, red
V = 1437.44 (10) Å³	0.15 × 0.08 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2479 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 28.5°, θ_min = 2.9°
φ and ω scans	h = −15→15
13963 measured reflections	k = −8→8
3654 independent reflections	l = −27→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0491P)² + 0.2765P] where P = (F_o² + 2F_c²)/3
3654 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.25 e Å⁻³
7 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

Special details top

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 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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.53655 (9)	0.28137 (15)	0.04401 (5)	0.0423 (3)
N1	0.71280 (9)	0.43066 (15)	0.14740 (5)	0.0306 (3)
N2	0.69480 (9)	0.54119 (16)	0.09243 (6)	0.0330 (3)
C1	0.75035 (12)	0.2025 (2)	0.26821 (7)	0.0410 (5)
C2	0.77274 (15)	0.0808 (3)	0.32550 (8)	0.0542 (6)
C3	0.71594 (15)	−0.1166 (3)	0.33086 (8)	0.0572 (6)
C4	0.63748 (13)	−0.1890 (2)	0.27889 (8)	0.0450 (5)
C5	0.61249 (11)	−0.0680 (2)	0.21974 (7)	0.0331 (4)
C6	0.53071 (11)	−0.1422 (2)	0.16480 (7)	0.0353 (4)
C7	0.50626 (11)	−0.0288 (2)	0.10759 (7)	0.0347 (4)
C8	0.56216 (11)	0.17470 (19)	0.09888 (6)	0.0306 (4)
C9	0.64717 (10)	0.25164 (18)	0.15195 (6)	0.0271 (3)
C10	0.67092 (10)	0.13066 (19)	0.21396 (6)	0.0300 (4)
C11A	0.75837 (19)	0.7234 (4)	0.08101 (11)	0.0240 (6)	0.750
C12A	0.73667 (19)	0.8278 (4)	0.01928 (10)	0.0317 (6)	0.750
C13A	0.7995 (2)	1.0103 (3)	0.00825 (12)	0.0358 (6)	0.750
C14A	0.8830 (2)	1.0934 (3)	0.05681 (16)	0.0308 (7)	0.750
C15A	0.9037 (2)	0.9908 (4)	0.11911 (16)	0.0308 (7)	0.750
C16A	0.8410 (3)	0.8045 (6)	0.13063 (13)	0.0296 (8)	0.750
C17A	0.94946 (19)	1.2939 (3)	0.04259 (12)	0.0460 (7)	0.750
C18A	0.98974 (19)	1.0814 (3)	0.17419 (11)	0.0488 (7)	0.750
C17B	0.9986 (5)	1.2864 (9)	0.0922 (4)	0.0434 (19)	0.250
C11B	0.7842 (8)	0.7320 (16)	0.1026 (4)	0.0278 (12)	0.250
C12B	0.8620 (9)	0.7828 (16)	0.1558 (4)	0.029 (2)	0.250
C13B	0.9316 (6)	0.9638 (11)	0.1505 (4)	0.0309 (19)	0.250
C14B	0.9186 (6)	1.0878 (11)	0.0925 (4)	0.0277 (19)	0.250
C15B	0.8400 (7)	1.0352 (11)	0.0381 (4)	0.0278 (12)	0.250
C16B	0.7699 (5)	0.8488 (11)	0.0447 (3)	0.0278 (12)	0.250
C18B	0.8259 (5)	1.1641 (8)	−0.0252 (3)	0.0397 (17)	0.250
H1	0.78830	0.33380	0.26540	0.0490*
H16A	0.85510	0.73500	0.17190	0.0360*	0.750
H17A	0.94450	1.39880	0.07720	0.0690*	0.750
H17B	0.91670	1.35310	0.00010	0.0690*	0.750
H17C	1.02930	1.25720	0.04140	0.0690*	0.750
H18A	0.96720	1.22560	0.18440	0.0730*	0.750
H18B	1.06530	1.08450	0.16020	0.0730*	0.750
H18C	0.99190	0.99230	0.21330	0.0730*	0.750
H2	0.64080	0.49950	0.06150	0.0400*
H2A	0.82600	0.12990	0.36100	0.0650*
H3	0.73160	−0.19840	0.36980	0.0690*
H4	0.60010	−0.32030	0.28270	0.0540*
H6	0.49320	−0.27330	0.16880	0.0420*
H7	0.45240	−0.08290	0.07320	0.0420*
H12A	0.68040	0.77500	−0.01410	0.0380*	0.750
H13A	0.78520	1.07920	−0.03310	0.0430*	0.750
H12B	0.86920	0.70040	0.19470	0.0340*	0.250
H13B	0.98730	1.00200	0.18630	0.0370*	0.250
H16B	0.71430	0.80710	0.00940	0.0330*	0.250
H17D	0.95230	1.41420	0.08330	0.0650*	0.250
H17E	1.04770	1.26890	0.05800	0.0650*	0.250
H17F	1.04580	1.29960	0.13500	0.0650*	0.250
H18D	0.79660	1.30500	−0.01680	0.0600*	0.250
H18E	0.77250	1.09190	−0.05850	0.0600*	0.250
H18F	0.89980	1.17800	−0.04090	0.0600*	0.250

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0527 (6)	0.0378 (5)	0.0358 (5)	−0.0014 (5)	0.0037 (4)	0.0018 (4)
N1	0.0310 (6)	0.0229 (5)	0.0405 (6)	0.0030 (4)	0.0137 (5)	0.0008 (4)
N2	0.0350 (6)	0.0236 (5)	0.0429 (6)	0.0000 (4)	0.0146 (5)	0.0035 (5)
C1	0.0379 (8)	0.0428 (8)	0.0426 (8)	−0.0006 (6)	0.0067 (6)	0.0035 (6)
C2	0.0505 (10)	0.0671 (11)	0.0436 (9)	0.0047 (8)	0.0014 (7)	0.0092 (8)
C3	0.0562 (10)	0.0673 (11)	0.0509 (9)	0.0157 (9)	0.0169 (8)	0.0304 (8)
C4	0.0427 (8)	0.0402 (8)	0.0569 (9)	0.0067 (7)	0.0239 (7)	0.0183 (7)
C5	0.0315 (7)	0.0277 (6)	0.0442 (7)	0.0046 (5)	0.0197 (6)	0.0058 (6)
C6	0.0343 (7)	0.0210 (6)	0.0554 (9)	−0.0021 (5)	0.0233 (6)	−0.0022 (6)
C7	0.0338 (7)	0.0283 (6)	0.0438 (7)	−0.0032 (5)	0.0121 (6)	−0.0086 (6)
C8	0.0338 (7)	0.0256 (6)	0.0347 (7)	0.0023 (5)	0.0132 (5)	−0.0022 (5)
C9	0.0282 (6)	0.0207 (6)	0.0346 (6)	0.0012 (5)	0.0124 (5)	−0.0003 (5)
C10	0.0287 (6)	0.0268 (6)	0.0368 (7)	0.0044 (5)	0.0132 (5)	0.0029 (5)
C11A	0.0219 (11)	0.0186 (8)	0.0329 (13)	0.0009 (8)	0.0090 (8)	0.0007 (10)
C12A	0.0317 (11)	0.0314 (9)	0.0328 (11)	0.0002 (8)	0.0078 (8)	0.0052 (9)
C13A	0.0395 (12)	0.0331 (10)	0.0369 (11)	0.0019 (9)	0.0127 (9)	0.0109 (9)
C14A	0.0312 (13)	0.0248 (11)	0.0390 (14)	0.0043 (9)	0.0146 (10)	0.0043 (11)
C15A	0.0263 (12)	0.0271 (12)	0.0398 (14)	0.0049 (9)	0.0070 (11)	−0.0004 (12)
C16A	0.0292 (16)	0.0276 (11)	0.0326 (15)	0.0044 (10)	0.0065 (13)	0.0048 (13)
C17A	0.0479 (12)	0.0290 (9)	0.0653 (14)	−0.0034 (9)	0.0227 (11)	0.0082 (10)
C18A	0.0447 (12)	0.0417 (11)	0.0579 (13)	−0.0088 (10)	−0.0004 (10)	0.0026 (10)
C17B	0.038 (3)	0.026 (3)	0.067 (4)	−0.010 (2)	0.010 (3)	0.001 (3)
C11B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C12B	0.023 (4)	0.023 (3)	0.039 (5)	−0.004 (3)	0.001 (4)	0.000 (4)
C13B	0.018 (3)	0.034 (3)	0.039 (4)	−0.002 (3)	−0.002 (3)	−0.005 (3)
C14B	0.032 (3)	0.022 (3)	0.032 (4)	0.002 (2)	0.015 (3)	0.011 (3)
C15B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C16B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C18B	0.045 (3)	0.027 (3)	0.052 (3)	−0.001 (2)	0.024 (3)	0.014 (2)

Geometric parameters (Å, º) top

O1—C8	1.2873 (15)	C15A—C18A	1.497 (4)
N1—N2	1.2946 (15)	C15A—C16A	1.401 (4)
N1—C9	1.3555 (15)	C15B—C16B	1.429 (10)
N2—C11A	1.385 (3)	C15B—C18B	1.495 (10)
N2—C11B	1.568 (10)	C1—H1	0.9300
N2—H2	0.8600	C2—H2A	0.9300
C1—C2	1.373 (2)	C3—H3	0.9300
C1—C10	1.4023 (18)	C4—H4	0.9300
C2—C3	1.400 (3)	C6—H6	0.9300
C3—C4	1.366 (2)	C7—H7	0.9300
C4—C5	1.404 (2)	C12A—H12A	0.9300
C5—C10	1.4171 (17)	C12B—H12B	0.9300
C5—C6	1.4316 (19)	C13A—H13A	0.9300
C6—C7	1.3465 (19)	C13B—H13B	0.9300
C7—C8	1.4390 (17)	C16A—H16A	0.9300
C8—C9	1.4335 (17)	C16B—H16B	0.9300
C9—C10	1.4507 (17)	C17A—H17C	0.9600
C11A—C12A	1.394 (3)	C17A—H17A	0.9600
C11A—C16A	1.382 (4)	C17A—H17B	0.9600
C11B—C16B	1.364 (11)	C17B—H17E	0.9600
C11B—C12B	1.341 (12)	C17B—H17F	0.9600
C12A—C13A	1.380 (3)	C17B—H17D	0.9600
C12B—C13B	1.395 (12)	C18A—H18C	0.9600
C13A—C14A	1.379 (4)	C18A—H18A	0.9600
C13B—C14B	1.390 (11)	C18A—H18B	0.9600
C14A—C17A	1.510 (3)	C18B—H18D	0.9600
C14A—C15A	1.398 (4)	C18B—H18E	0.9600
C14B—C17B	1.542 (9)	C18B—H18F	0.9600
C14B—C15B	1.366 (11)

N2—N1—C9	117.66 (10)	C2—C1—H1	120.00
N1—N2—C11A	123.10 (13)	C10—C1—H1	120.00
N1—N2—C11B	105.1 (3)	C1—C2—H2A	120.00
C11B—N2—H2	136.00	C3—C2—H2A	120.00
N1—N2—H2	118.00	C2—C3—H3	120.00
C11A—N2—H2	118.00	C4—C3—H3	120.00
C2—C1—C10	120.65 (13)	C3—C4—H4	120.00
C1—C2—C3	120.47 (15)	C5—C4—H4	119.00
C2—C3—C4	119.93 (15)	C5—C6—H6	119.00
C3—C4—C5	120.95 (13)	C7—C6—H6	119.00
C6—C5—C10	119.27 (12)	C6—C7—H7	119.00
C4—C5—C6	121.55 (12)	C8—C7—H7	120.00
C4—C5—C10	119.18 (12)	C11A—C12A—H12A	120.00
C5—C6—C7	122.30 (12)	C13A—C12A—H12A	120.00
C6—C7—C8	121.03 (12)	C11B—C12B—H12B	121.00
O1—C8—C7	119.95 (11)	C13B—C12B—H12B	121.00
O1—C8—C9	121.64 (11)	C12A—C13A—H13A	119.00
C7—C8—C9	118.41 (11)	C14A—C13A—H13A	119.00
N1—C9—C10	116.02 (10)	C14B—C13B—H13B	120.00
C8—C9—C10	120.07 (10)	C12B—C13B—H13B	120.00
N1—C9—C8	123.86 (11)	C15A—C16A—H16A	120.00
C1—C10—C9	122.33 (11)	C11A—C16A—H16A	120.00
C1—C10—C5	118.82 (11)	C11B—C16B—H16B	120.00
C5—C10—C9	118.85 (11)	C15B—C16B—H16B	120.00
N2—C11A—C12A	119.43 (19)	H17A—C17A—H17B	110.00
N2—C11A—C16A	120.6 (2)	H17A—C17A—H17C	110.00
C12A—C11A—C16A	120.0 (2)	C14A—C17A—H17A	109.00
N2—C11B—C12B	130.0 (8)	C14A—C17A—H17B	109.00
C12B—C11B—C16B	123.3 (9)	C14A—C17A—H17C	109.00
N2—C11B—C16B	106.7 (6)	H17B—C17A—H17C	109.00
C11A—C12A—C13A	119.3 (2)	C14B—C17B—H17D	110.00
C11B—C12B—C13B	117.5 (8)	H17D—C17B—H17E	109.00
C12A—C13A—C14A	121.8 (2)	H17D—C17B—H17F	110.00
C12B—C13B—C14B	120.8 (7)	H17E—C17B—H17F	109.00
C13A—C14A—C15A	119.0 (2)	C14B—C17B—H17E	109.00
C15A—C14A—C17A	121.0 (2)	C14B—C17B—H17F	110.00
C13A—C14A—C17A	120.0 (2)	H18B—C18A—H18C	109.00
C13B—C14B—C17B	116.6 (7)	H18A—C18A—H18B	109.00
C13B—C14B—C15B	121.8 (7)	H18A—C18A—H18C	110.00
C15B—C14B—C17B	121.6 (7)	C15A—C18A—H18A	109.00
C14A—C15A—C16A	119.6 (2)	C15A—C18A—H18B	110.00
C14A—C15A—C18A	120.7 (2)	C15A—C18A—H18C	109.00
C16A—C15A—C18A	119.7 (3)	C15B—C18B—H18D	109.00
C14B—C15B—C16B	116.4 (7)	C15B—C18B—H18E	109.00
C14B—C15B—C18B	122.7 (6)	C15B—C18B—H18F	109.00
C16B—C15B—C18B	120.9 (6)	H18D—C18B—H18E	110.00
C11A—C16A—C15A	120.3 (3)	H18D—C18B—H18F	109.00
C11B—C16B—C15B	120.3 (7)	H18E—C18B—H18F	109.00

C9—N1—N2—C11A	−178.13 (15)	O1—C8—C9—N1	−4.99 (19)
N2—N1—C9—C8	2.05 (17)	O1—C8—C9—C10	177.92 (11)
N2—N1—C9—C10	179.25 (10)	C7—C8—C9—N1	174.01 (11)
N1—N2—C11A—C12A	177.29 (17)	C7—C8—C9—C10	−3.08 (17)
N1—N2—C11A—C16A	−4.1 (3)	N1—C9—C10—C1	4.86 (17)
C10—C1—C2—C3	−0.4 (2)	N1—C9—C10—C5	−174.62 (11)
C2—C1—C10—C5	1.2 (2)	C8—C9—C10—C1	−177.83 (12)
C2—C1—C10—C9	−178.34 (13)	C8—C9—C10—C5	2.69 (17)
C1—C2—C3—C4	−0.1 (3)	N2—C11A—C12A—C13A	179.48 (19)
C2—C3—C4—C5	−0.1 (2)	C16A—C11A—C12A—C13A	0.8 (4)
C3—C4—C5—C6	179.81 (14)	N2—C11A—C16A—C15A	−179.0 (2)
C3—C4—C5—C10	0.8 (2)	C12A—C11A—C16A—C15A	−0.4 (4)
C4—C5—C6—C7	−179.60 (13)	C11A—C12A—C13A—C14A	−0.4 (3)
C10—C5—C6—C7	−0.6 (2)	C12A—C13A—C14A—C15A	−0.6 (3)
C4—C5—C10—C1	−1.30 (19)	C12A—C13A—C14A—C17A	−179.8 (2)
C4—C5—C10—C9	178.20 (12)	C13A—C14A—C15A—C16A	1.1 (4)
C6—C5—C10—C1	179.63 (12)	C13A—C14A—C15A—C18A	−177.2 (2)
C6—C5—C10—C9	−0.87 (18)	C17A—C14A—C15A—C16A	−179.7 (2)
C5—C6—C7—C8	0.1 (2)	C17A—C14A—C15A—C18A	2.0 (3)
C6—C7—C8—O1	−179.29 (12)	C14A—C15A—C16A—C11A	−0.6 (4)
C6—C7—C8—C9	1.69 (19)	C18A—C15A—C16A—C11A	177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.82	2.5347 (15)	140
C12A—H12A···O1ⁱ	0.93	2.54	3.325 (2)	143

Symmetry code: (i) −x+1, −y+1, −z.

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(E)-1-[2-(3,4-Di­methyl­phen­yl)diazen-2-ium-1-yl]naphthalen-2-olate

Supporting information

Key indicators

checkCIF/PLATON results

(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate