organic compounds
(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria, bLaboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and cFaculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador, Morocco
*Correspondence e-mail: souheilachetioui@yahoo.fr
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.
CCDC reference: 1532675
Structure description
For general background to ); Tao et al. (1999).
and their use in dyes, pigments and advanced materials, see: Navarro & Sanz (1999The title azo dye adopts the zwitterionic form in the crystal (Fig. 1), with proton transfer from the phenol group to the azo group, which allows for the formation of an intramolecular N—H⋯O hydrogen bond (Table 1). The dimethyl benzene ring is disordered by ∼180° rotation about the N2—C11 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)°.
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In the crystal, molecules are linked by aromatic π–π stacking between the benzene rings and the naphthalene ring systems of adjacent molecules, the centroid–centroid distances of 3.574 (3) and 3.5754 (12) Å, respectively, between the C5–C10 and C11B–C16B(x, y − 1, z) rings and between the C5–C10 and C11A–C16A(x, y − 1, z) rings. C—H—O hydrogen bonds are also observed, forming chains running parallel to the a-axis direction (Table 1, Fig. 2).
Synthesis and crystallization
The title compound was synthesized according to a literature method (Wang et al., 2003), viz. the diazotization of 3,4-dimethylaniline followed by a coupling reaction with 2-naphthol. Red prisms were obtained by slow evaporation of an acetone solution at room temperature (yield 88%).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1532675
https://doi.org/10.1107/S2414314617002590/hb4118sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002590/hb4118Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002590/hb4118Isup3.cml
Data collection: APEX2 (Bruker, 2006); cell
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).C18H16N2O | F(000) = 584 |
Mr = 276.33 | Dx = 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 |
Bruker APEXII CCD diffractometer | 2479 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 28.5°, θmin = 2.9° |
φ and ω scans | h = −15→15 |
13963 measured reflections | k = −8→8 |
3654 independent reflections | l = −27→27 |
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(Fo2) + (0.0491P)2 + 0.2765P] where P = (Fo2 + 2Fc2)/3 |
3654 reflections | (Δ/σ)max < 0.001 |
254 parameters | Δρmax = 0.25 e Å−3 |
7 restraints | Δρmin = −0.23 e Å−3 |
0 constraints |
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. |
x | y | z | Uiso*/Ueq | 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 |
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) |
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) |
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. |
Funding information
Funding for this research was provided by: Ministère de l'Enseignement Supérieur et de la Recherche Scientifiquehttps://doi.org/10.13039/501100002717Direction Générale de la Recherche Scientifique et du Développement Technologiquehttps://doi.org/10.13039/501100005307University of Constantine
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