organic compounds
2-{[(2-Methoxynaphthalen-1-yl)methyl]amino}phenol
aLaboratory for Synthesis of Molecules of Biological Interest, University of Constantine 1, 25000 Constantine, Algeria, and bResearch Unit of Chemistry of the Environment and Molecular Structure, Department of Chemistry, University of Constantine 1, Algeria
*Correspondence e-mail: gnd1sr811@hotmail.com
The 18H17NO2, contains two independent molecules (A and B). The dihedral angle between the naphthalene ring system and the benzene ring is 74.67 (10)° in molecule A and 78.81 (9)° in molecule B. In the crystal, molecules are linked by a series of C—H⋯π interactions, forming sheets parallel to the ab plane.
of the title compound, CCCDC reference: 1494062
Structure description
Aromatic ). In view of this interest we have synthesized the title amino-phenol derivative, which was obtained by reduction of the initially prepared Schiff base, and report herein on its crystal structure.
and aminophenols, are of considerable importance for their industrial, toxicological and pharmaceutical aspects (Kirk-Othmer, 1979The title compound, Fig. 1, crystallized with two independent molecules (A and B) in the The naphthalene ring system and the benzene ring are inclined to one another by 74.67 (10)° in molecule A and 78.81 (9)° in molecule B. The bridging C—N bond lengths are single bonds as confirmed by their bond lengths; C7—N1 = 1.464 (2) Å in molecule A, and C25—N2 = 1.462 (2) Å in molecule B.
In the crystal, molecules are linked by a series of C—H⋯π interactions (Table 1) forming sheets lying parallel to (001); see Fig. 2. There are no other significant intermolecular interactions present.
Synthesis and crystallization
A mixture of 2-aminophenol (3 mmol) and 2-methoxy-1-naphthaldehyde (3 mmol) in methanol (10 mmol) was stirred at room temperature for 24 h. On completion of this condensation reaction (monitored by thin layer chromatography), NaBH3CN (4.5 mmol) was added and stirring was continued for 24 h. On completion of the reaction (monitored by thin layer chromatography), the mixture was poured over ice–water. The resulting precipitate was filtered, washed with water and dried. The resulting light-brown fine powder of the title compound was obtained in very high purity with excellent yield.
Spectroscopic data: IR (KBr,cm−1) ν: 3476; 3418; 1601; 1258. 1HNMR (400 MHz, CDCl3) δ 8.04 (d, J = 8.6 Hz, 1H); 7.88 (d, J = 9.1 Hz, 1H); 7.84 (d,J = 8.6 Hz, 1H); 7.51 (t, J = 7.7 Hz, 1H); 7.39 (t, J = 7.5 Hz, 1H); 7.34 (d, J = 9.1 Hz, 1H); 7.04 (d, J = 7.9 Hz, 1H); 6.96 (t, J = 7.5 Hz, 1H); 6.81–6.72 (m, 2H); 4.71 (s, 2H); 3.99 (s, 2H). 13CNMR (101 MHz, CDCl3) δ 155.26; 145.11; 137.23; 133.28; 129.71; 129.20; 128.49; 127.04; 123.59; 123.11; 121.42;119.48; 119.00;114.45;114.33; 113.32; 56.72; 39.49. HRMS: (M +.Na)+, found 302.1180,C18H17NO2Na requires 302.1157.
Refinement
Crystal data, data collection and structure . Three reflections (031, 002, 013), affected by the backstop were omitted from the final cycles of refinement.
details are summarized in Table 2
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Structural data
CCDC reference: 1494062
https://doi.org/10.1107/S2414314616011603/su4065sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616011603/su4065Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616011603/su4065Isup3.cml
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C18H16NO2 | F(000) = 1176 |
Mr = 278.32 | Dx = 1.222 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1402 (5) Å | Cell parameters from 8065 reflections |
b = 19.3384 (14) Å | θ = 3.1–25.5° |
c = 22.0655 (17) Å | µ = 0.08 mm−1 |
β = 96.874 (4)° | T = 293 K |
V = 3024.9 (4) Å3 | Block, orange |
Z = 8 | 0.03 × 0.02 × 0.01 mm |
Bruker APEXII CCD diffractometer | 3608 reflections with I > 2σ(I) |
Radiation source: Bruker–Nonius FR591 rotating anode | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
Detector resolution: 18.4 pixels mm-1 | h = −5→8 |
φ and ω scans | k = −22→21 |
19509 measured reflections | l = −26→26 |
5337 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.167 | w = 1/[σ2(Fo2) + (0.0903P)2 + 0.6386P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5337 reflections | Δρmax = 0.33 e Å−3 |
390 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (12) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1871 (3) | 0.57240 (10) | 0.20335 (8) | 0.0911 (6) | |
O2 | −0.0327 (2) | 0.36826 (8) | 0.29552 (7) | 0.0677 (5) | |
N1 | 0.0977 (2) | 0.48913 (8) | 0.21416 (8) | 0.0485 (4) | |
H34 | 0.036 (3) | 0.5017 (11) | 0.2456 (11) | 0.065 (7)* | |
C1 | −0.0168 (3) | 0.48804 (10) | 0.15803 (9) | 0.0479 (5) | |
C2 | −0.1693 (3) | 0.53455 (13) | 0.15179 (10) | 0.0626 (6) | |
C3 | −0.2816 (4) | 0.54052 (17) | 0.09782 (13) | 0.0850 (8) | |
H3 | −0.3818 | 0.5716 | 0.0939 | 0.102* | |
C4 | −0.2460 (4) | 0.50012 (19) | 0.04878 (13) | 0.0938 (10) | |
H4 | −0.3229 | 0.5041 | 0.0118 | 0.113* | |
C5 | −0.0975 (4) | 0.45394 (16) | 0.05404 (11) | 0.0854 (8) | |
H5 | −0.0751 | 0.4269 | 0.0208 | 0.103* | |
C6 | 0.0185 (3) | 0.44792 (12) | 0.10900 (10) | 0.0628 (6) | |
H6 | 0.1191 | 0.4171 | 0.1127 | 0.075* | |
C7 | 0.2195 (3) | 0.43007 (10) | 0.23271 (9) | 0.0497 (5) | |
H7A | 0.3384 | 0.4350 | 0.2160 | 0.060* | |
H7B | 0.1597 | 0.3878 | 0.2166 | 0.060* | |
C8 | 0.2561 (3) | 0.42537 (9) | 0.30118 (9) | 0.0460 (5) | |
C9 | 0.1217 (3) | 0.39253 (10) | 0.33156 (9) | 0.0510 (5) | |
C10 | 0.1471 (3) | 0.38502 (11) | 0.39523 (10) | 0.0610 (6) | |
H10 | 0.0549 | 0.3635 | 0.4149 | 0.073* | |
C11 | 0.3070 (3) | 0.40930 (12) | 0.42812 (10) | 0.0633 (6) | |
H11 | 0.3242 | 0.4029 | 0.4702 | 0.076* | |
C12 | 0.6122 (3) | 0.47032 (13) | 0.43392 (11) | 0.0691 (7) | |
H12 | 0.6322 | 0.4629 | 0.4758 | 0.083* | |
C13 | 0.7428 (4) | 0.50649 (14) | 0.40637 (13) | 0.0779 (7) | |
H13 | 0.8501 | 0.5239 | 0.4294 | 0.094* | |
C14 | 0.7139 (3) | 0.51724 (13) | 0.34319 (12) | 0.0718 (7) | |
H14 | 0.8017 | 0.5425 | 0.3245 | 0.086* | |
C15 | 0.5591 (3) | 0.49120 (11) | 0.30879 (10) | 0.0576 (6) | |
H15 | 0.5441 | 0.4984 | 0.2668 | 0.069* | |
C16 | 0.4474 (3) | 0.44400 (10) | 0.39997 (9) | 0.0538 (5) | |
C17 | 0.4198 (3) | 0.45330 (10) | 0.33556 (9) | 0.0469 (5) | |
C18 | −0.1706 (4) | 0.32928 (14) | 0.32310 (13) | 0.0824 (8) | |
H18A | −0.2216 | 0.3573 | 0.3531 | 0.124* | |
H18B | −0.1124 | 0.2889 | 0.3423 | 0.124* | |
H18C | −0.2702 | 0.3156 | 0.2923 | 0.124* | |
O3 | 0.6832 (3) | 0.10351 (9) | 0.29302 (7) | 0.0796 (5) | |
O4 | 0.5217 (2) | 0.30583 (9) | 0.17915 (8) | 0.0802 (5) | |
N2 | 0.4025 (2) | 0.18845 (8) | 0.27327 (8) | 0.0505 (4) | |
H35 | 0.465 (3) | 0.1718 (11) | 0.2442 (10) | 0.061 (7)* | |
C19 | 0.5112 (3) | 0.19270 (9) | 0.33008 (8) | 0.0434 (4) | |
C20 | 0.6598 (3) | 0.14551 (10) | 0.34137 (9) | 0.0519 (5) | |
C21 | 0.7683 (3) | 0.14390 (12) | 0.39699 (10) | 0.0660 (6) | |
H21 | 0.8673 | 0.1126 | 0.4041 | 0.079* | |
C22 | 0.7296 (4) | 0.18927 (13) | 0.44263 (10) | 0.0733 (7) | |
H22 | 0.8024 | 0.1881 | 0.4805 | 0.088* | |
C23 | 0.5849 (4) | 0.23555 (13) | 0.43210 (10) | 0.0711 (7) | |
H23 | 0.5603 | 0.2661 | 0.4627 | 0.085* | |
C24 | 0.4743 (3) | 0.23732 (11) | 0.37598 (9) | 0.0562 (5) | |
H24 | 0.3751 | 0.2686 | 0.3693 | 0.067* | |
C25 | 0.2839 (3) | 0.24647 (10) | 0.24990 (9) | 0.0499 (5) | |
H25A | 0.3471 | 0.2896 | 0.2618 | 0.060* | |
H25B | 0.1659 | 0.2453 | 0.2676 | 0.060* | |
C26 | 0.2444 (3) | 0.24313 (10) | 0.18170 (9) | 0.0482 (5) | |
C27 | 0.3695 (3) | 0.27438 (12) | 0.14705 (10) | 0.0592 (6) | |
C28 | 0.3399 (4) | 0.27346 (14) | 0.08317 (11) | 0.0731 (7) | |
H28 | 0.4241 | 0.2958 | 0.0607 | 0.088* | |
C29 | 0.1871 (4) | 0.23974 (15) | 0.05396 (11) | 0.0753 (7) | |
H29 | 0.1690 | 0.2390 | 0.0115 | 0.090* | |
C30 | −0.1031 (4) | 0.17011 (15) | 0.05697 (11) | 0.0787 (8) | |
H30 | −0.1222 | 0.1687 | 0.0145 | 0.094* | |
C31 | −0.2272 (4) | 0.13796 (15) | 0.08931 (13) | 0.0841 (8) | |
H31 | −0.3311 | 0.1151 | 0.0691 | 0.101* | |
C32 | −0.1988 (3) | 0.13913 (14) | 0.15317 (12) | 0.0732 (7) | |
H32 | −0.2838 | 0.1166 | 0.1752 | 0.088* | |
C33 | −0.0489 (3) | 0.17276 (11) | 0.18333 (10) | 0.0575 (6) | |
H33 | −0.0331 | 0.1729 | 0.2258 | 0.069* | |
C34 | 0.0559 (3) | 0.20595 (12) | 0.08671 (9) | 0.0592 (6) | |
C35 | 0.0839 (3) | 0.20765 (10) | 0.15160 (9) | 0.0484 (5) | |
C36 | 0.6600 (4) | 0.33821 (17) | 0.14691 (15) | 0.1022 (10) | |
H36A | 0.6016 | 0.3742 | 0.1213 | 0.153* | |
H36B | 0.7138 | 0.3045 | 0.1221 | 0.153* | |
H36C | 0.7575 | 0.3577 | 0.1756 | 0.153* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1044 (14) | 0.0957 (14) | 0.0720 (12) | 0.0467 (11) | 0.0064 (10) | −0.0047 (10) |
O2 | 0.0568 (9) | 0.0696 (10) | 0.0770 (11) | −0.0108 (8) | 0.0097 (8) | 0.0033 (8) |
N1 | 0.0571 (10) | 0.0414 (9) | 0.0465 (10) | 0.0043 (8) | 0.0043 (8) | −0.0019 (7) |
C1 | 0.0505 (11) | 0.0438 (11) | 0.0491 (11) | −0.0077 (9) | 0.0041 (9) | 0.0028 (9) |
C2 | 0.0565 (13) | 0.0701 (15) | 0.0598 (14) | 0.0024 (11) | 0.0013 (11) | 0.0110 (11) |
C3 | 0.0667 (16) | 0.111 (2) | 0.0745 (18) | 0.0090 (15) | −0.0030 (14) | 0.0142 (16) |
C4 | 0.0795 (19) | 0.127 (3) | 0.0678 (18) | −0.0158 (19) | −0.0209 (15) | 0.0121 (17) |
C5 | 0.099 (2) | 0.099 (2) | 0.0555 (15) | −0.0185 (18) | 0.0002 (14) | −0.0131 (14) |
C6 | 0.0702 (14) | 0.0609 (14) | 0.0567 (13) | −0.0064 (11) | 0.0053 (11) | −0.0063 (11) |
C7 | 0.0540 (12) | 0.0430 (11) | 0.0527 (12) | 0.0063 (9) | 0.0089 (9) | 0.0002 (9) |
C8 | 0.0494 (11) | 0.0389 (10) | 0.0507 (11) | 0.0081 (9) | 0.0095 (9) | 0.0021 (8) |
C9 | 0.0507 (12) | 0.0441 (11) | 0.0591 (13) | 0.0049 (9) | 0.0111 (10) | 0.0012 (9) |
C10 | 0.0671 (15) | 0.0565 (13) | 0.0635 (14) | 0.0050 (11) | 0.0246 (12) | 0.0077 (11) |
C11 | 0.0817 (16) | 0.0606 (14) | 0.0493 (12) | 0.0118 (12) | 0.0153 (12) | 0.0035 (10) |
C12 | 0.0743 (16) | 0.0722 (16) | 0.0583 (14) | 0.0082 (13) | −0.0020 (12) | −0.0083 (12) |
C13 | 0.0675 (16) | 0.0799 (18) | 0.0830 (19) | −0.0028 (14) | −0.0052 (14) | −0.0174 (14) |
C14 | 0.0628 (15) | 0.0678 (16) | 0.0856 (18) | −0.0075 (12) | 0.0126 (13) | −0.0021 (13) |
C15 | 0.0577 (13) | 0.0556 (13) | 0.0599 (13) | 0.0023 (10) | 0.0086 (10) | 0.0036 (10) |
C16 | 0.0616 (13) | 0.0477 (12) | 0.0522 (12) | 0.0085 (10) | 0.0070 (10) | −0.0027 (9) |
C17 | 0.0508 (11) | 0.0391 (10) | 0.0512 (12) | 0.0092 (9) | 0.0081 (9) | 0.0002 (8) |
C18 | 0.0679 (16) | 0.0728 (17) | 0.109 (2) | −0.0173 (13) | 0.0211 (15) | 0.0093 (15) |
O3 | 0.1055 (13) | 0.0722 (11) | 0.0563 (9) | 0.0390 (10) | −0.0105 (9) | −0.0142 (8) |
O4 | 0.0653 (10) | 0.0875 (12) | 0.0884 (12) | −0.0206 (9) | 0.0123 (9) | −0.0064 (10) |
N2 | 0.0565 (10) | 0.0452 (10) | 0.0478 (10) | 0.0052 (8) | −0.0023 (8) | −0.0056 (8) |
C19 | 0.0473 (11) | 0.0378 (10) | 0.0445 (10) | −0.0024 (8) | 0.0031 (8) | 0.0008 (8) |
C20 | 0.0644 (13) | 0.0432 (11) | 0.0467 (11) | 0.0040 (10) | 0.0008 (10) | 0.0004 (9) |
C21 | 0.0757 (15) | 0.0593 (14) | 0.0594 (14) | 0.0150 (12) | −0.0068 (12) | 0.0027 (11) |
C22 | 0.0942 (18) | 0.0718 (16) | 0.0484 (13) | 0.0101 (14) | −0.0144 (12) | −0.0019 (12) |
C23 | 0.0920 (18) | 0.0707 (16) | 0.0488 (13) | 0.0123 (14) | 0.0014 (12) | −0.0127 (11) |
C24 | 0.0600 (13) | 0.0543 (13) | 0.0537 (12) | 0.0075 (10) | 0.0044 (10) | −0.0056 (10) |
C25 | 0.0513 (11) | 0.0456 (11) | 0.0511 (12) | 0.0075 (9) | −0.0010 (9) | −0.0047 (9) |
C26 | 0.0499 (11) | 0.0429 (11) | 0.0512 (11) | 0.0081 (9) | 0.0038 (9) | 0.0007 (9) |
C27 | 0.0569 (13) | 0.0569 (13) | 0.0644 (14) | 0.0042 (11) | 0.0096 (11) | −0.0017 (11) |
C28 | 0.0769 (17) | 0.0784 (17) | 0.0675 (16) | 0.0005 (14) | 0.0235 (13) | 0.0088 (13) |
C29 | 0.0848 (18) | 0.0942 (19) | 0.0476 (13) | 0.0106 (15) | 0.0113 (13) | 0.0050 (12) |
C30 | 0.0834 (18) | 0.096 (2) | 0.0524 (14) | 0.0044 (15) | −0.0083 (13) | −0.0116 (13) |
C31 | 0.0751 (17) | 0.093 (2) | 0.0795 (18) | −0.0124 (15) | −0.0106 (15) | −0.0173 (15) |
C32 | 0.0689 (15) | 0.0786 (17) | 0.0711 (16) | −0.0131 (13) | 0.0044 (13) | −0.0021 (13) |
C33 | 0.0617 (13) | 0.0588 (13) | 0.0506 (12) | 0.0016 (11) | 0.0007 (10) | 0.0011 (10) |
C34 | 0.0645 (14) | 0.0640 (14) | 0.0478 (12) | 0.0099 (11) | 0.0011 (10) | −0.0017 (10) |
C35 | 0.0517 (11) | 0.0459 (11) | 0.0464 (11) | 0.0102 (9) | 0.0003 (9) | 0.0002 (9) |
C36 | 0.0808 (19) | 0.102 (2) | 0.127 (3) | −0.0285 (17) | 0.0257 (18) | 0.0137 (19) |
O1—C2 | 1.371 (3) | O3—C20 | 1.367 (2) |
O2—C9 | 1.363 (3) | O4—C27 | 1.367 (3) |
O2—C18 | 1.432 (3) | O4—C36 | 1.429 (3) |
N1—C1 | 1.400 (3) | N2—C19 | 1.395 (2) |
N1—C7 | 1.464 (2) | N2—C25 | 1.462 (2) |
N1—H34 | 0.90 (2) | N2—H35 | 0.88 (2) |
C1—C6 | 1.379 (3) | C19—C24 | 1.380 (3) |
C1—C2 | 1.407 (3) | C19—C20 | 1.399 (3) |
C2—C3 | 1.359 (3) | C20—C21 | 1.371 (3) |
C3—C4 | 1.383 (4) | C21—C22 | 1.388 (3) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.381 (4) | C22—C23 | 1.366 (3) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.389 (3) | C23—C24 | 1.387 (3) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—C8 | 1.505 (3) | C25—C26 | 1.499 (3) |
C7—H7A | 0.9700 | C25—H25A | 0.9700 |
C7—H7B | 0.9700 | C25—H25B | 0.9700 |
C8—C9 | 1.388 (3) | C26—C27 | 1.383 (3) |
C8—C17 | 1.422 (3) | C26—C35 | 1.429 (3) |
C9—C10 | 1.402 (3) | C27—C28 | 1.400 (3) |
C10—C11 | 1.361 (3) | C28—C29 | 1.365 (4) |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—C16 | 1.411 (3) | C29—C34 | 1.410 (3) |
C11—H11 | 0.9300 | C29—H29 | 0.9300 |
C12—C13 | 1.365 (4) | C30—C31 | 1.354 (4) |
C12—C16 | 1.412 (3) | C30—C34 | 1.422 (3) |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C14 | 1.400 (4) | C31—C32 | 1.400 (4) |
C13—H13 | 0.9300 | C31—H31 | 0.9300 |
C14—C15 | 1.360 (3) | C32—C33 | 1.357 (3) |
C14—H14 | 0.9300 | C32—H32 | 0.9300 |
C15—C17 | 1.420 (3) | C33—C35 | 1.415 (3) |
C15—H15 | 0.9300 | C33—H33 | 0.9300 |
C16—C17 | 1.423 (3) | C34—C35 | 1.422 (3) |
C18—H18A | 0.9600 | C36—H36A | 0.9600 |
C18—H18B | 0.9600 | C36—H36B | 0.9600 |
C18—H18C | 0.9600 | C36—H36C | 0.9600 |
C9—O2—C18 | 118.85 (18) | C27—O4—C36 | 119.4 (2) |
C1—N1—C7 | 120.01 (16) | C19—N2—C25 | 120.54 (16) |
C1—N1—H34 | 113.4 (14) | C19—N2—H35 | 113.6 (14) |
C7—N1—H34 | 109.0 (14) | C25—N2—H35 | 110.1 (14) |
C6—C1—N1 | 124.09 (19) | C24—C19—N2 | 124.18 (18) |
C6—C1—C2 | 119.7 (2) | C24—C19—C20 | 118.99 (18) |
N1—C1—C2 | 116.13 (18) | N2—C19—C20 | 116.73 (17) |
C3—C2—O1 | 125.3 (2) | O3—C20—C21 | 125.2 (2) |
C3—C2—C1 | 120.6 (2) | O3—C20—C19 | 114.18 (17) |
O1—C2—C1 | 114.05 (19) | C21—C20—C19 | 120.63 (19) |
C2—C3—C4 | 119.6 (3) | C20—C21—C22 | 119.7 (2) |
C2—C3—H3 | 120.2 | C20—C21—H21 | 120.2 |
C4—C3—H3 | 120.2 | C22—C21—H21 | 120.2 |
C5—C4—C3 | 120.7 (3) | C23—C22—C21 | 120.2 (2) |
C5—C4—H4 | 119.6 | C23—C22—H22 | 119.9 |
C3—C4—H4 | 119.6 | C21—C22—H22 | 119.9 |
C4—C5—C6 | 119.9 (3) | C22—C23—C24 | 120.4 (2) |
C4—C5—H5 | 120.0 | C22—C23—H23 | 119.8 |
C6—C5—H5 | 120.0 | C24—C23—H23 | 119.8 |
C1—C6—C5 | 119.5 (2) | C19—C24—C23 | 120.1 (2) |
C1—C6—H6 | 120.3 | C19—C24—H24 | 119.9 |
C5—C6—H6 | 120.3 | C23—C24—H24 | 119.9 |
N1—C7—C8 | 110.71 (15) | N2—C25—C26 | 110.65 (16) |
N1—C7—H7A | 109.5 | N2—C25—H25A | 109.5 |
C8—C7—H7A | 109.5 | C26—C25—H25A | 109.5 |
N1—C7—H7B | 109.5 | N2—C25—H25B | 109.5 |
C8—C7—H7B | 109.5 | C26—C25—H25B | 109.5 |
H7A—C7—H7B | 108.1 | H25A—C25—H25B | 108.1 |
C9—C8—C17 | 119.19 (18) | C27—C26—C35 | 119.22 (19) |
C9—C8—C7 | 117.74 (18) | C27—C26—C25 | 118.67 (19) |
C17—C8—C7 | 123.07 (17) | C35—C26—C25 | 122.11 (18) |
O2—C9—C8 | 115.68 (18) | O4—C27—C26 | 115.7 (2) |
O2—C9—C10 | 123.19 (19) | O4—C27—C28 | 122.9 (2) |
C8—C9—C10 | 121.1 (2) | C26—C27—C28 | 121.4 (2) |
C11—C10—C9 | 119.9 (2) | C29—C28—C27 | 119.8 (2) |
C11—C10—H10 | 120.1 | C29—C28—H28 | 120.1 |
C9—C10—H10 | 120.1 | C27—C28—H28 | 120.1 |
C10—C11—C16 | 121.6 (2) | C28—C29—C34 | 121.5 (2) |
C10—C11—H11 | 119.2 | C28—C29—H29 | 119.3 |
C16—C11—H11 | 119.2 | C34—C29—H29 | 119.3 |
C13—C12—C16 | 121.2 (2) | C31—C30—C34 | 121.2 (2) |
C13—C12—H12 | 119.4 | C31—C30—H30 | 119.4 |
C16—C12—H12 | 119.4 | C34—C30—H30 | 119.4 |
C12—C13—C14 | 119.5 (2) | C30—C31—C32 | 119.9 (2) |
C12—C13—H13 | 120.2 | C30—C31—H31 | 120.1 |
C14—C13—H13 | 120.2 | C32—C31—H31 | 120.1 |
C15—C14—C13 | 120.9 (2) | C33—C32—C31 | 120.8 (2) |
C15—C14—H14 | 119.6 | C33—C32—H32 | 119.6 |
C13—C14—H14 | 119.6 | C31—C32—H32 | 119.6 |
C14—C15—C17 | 121.5 (2) | C32—C33—C35 | 121.4 (2) |
C14—C15—H15 | 119.3 | C32—C33—H33 | 119.3 |
C17—C15—H15 | 119.3 | C35—C33—H33 | 119.3 |
C11—C16—C12 | 121.9 (2) | C29—C34—C35 | 118.9 (2) |
C11—C16—C17 | 118.6 (2) | C29—C34—C30 | 122.1 (2) |
C12—C16—C17 | 119.4 (2) | C35—C34—C30 | 119.0 (2) |
C15—C17—C8 | 123.10 (18) | C33—C35—C34 | 117.73 (19) |
C15—C17—C16 | 117.43 (19) | C33—C35—C26 | 123.11 (18) |
C8—C17—C16 | 119.47 (18) | C34—C35—C26 | 119.15 (19) |
O2—C18—H18A | 109.5 | O4—C36—H36A | 109.5 |
O2—C18—H18B | 109.5 | O4—C36—H36B | 109.5 |
H18A—C18—H18B | 109.5 | H36A—C36—H36B | 109.5 |
O2—C18—H18C | 109.5 | O4—C36—H36C | 109.5 |
H18A—C18—H18C | 109.5 | H36A—C36—H36C | 109.5 |
H18B—C18—H18C | 109.5 | H36B—C36—H36C | 109.5 |
C7—N1—C1—C6 | −23.4 (3) | C25—N2—C19—C24 | 22.2 (3) |
C7—N1—C1—C2 | 160.56 (18) | C25—N2—C19—C20 | −161.57 (18) |
C6—C1—C2—C3 | −0.3 (3) | C24—C19—C20—O3 | 179.58 (19) |
N1—C1—C2—C3 | 175.9 (2) | N2—C19—C20—O3 | 3.1 (3) |
C6—C1—C2—O1 | −178.7 (2) | C24—C19—C20—C21 | −0.5 (3) |
N1—C1—C2—O1 | −2.6 (3) | N2—C19—C20—C21 | −177.0 (2) |
O1—C2—C3—C4 | 178.6 (3) | O3—C20—C21—C22 | −179.8 (2) |
C1—C2—C3—C4 | 0.4 (4) | C19—C20—C21—C22 | 0.4 (4) |
C2—C3—C4—C5 | −0.1 (4) | C20—C21—C22—C23 | −0.4 (4) |
C3—C4—C5—C6 | −0.3 (4) | C21—C22—C23—C24 | 0.5 (4) |
N1—C1—C6—C5 | −175.9 (2) | N2—C19—C24—C23 | 176.8 (2) |
C2—C1—C6—C5 | −0.1 (3) | C20—C19—C24—C23 | 0.7 (3) |
C4—C5—C6—C1 | 0.4 (4) | C22—C23—C24—C19 | −0.7 (4) |
C1—N1—C7—C8 | −153.22 (18) | C19—N2—C25—C26 | 157.18 (18) |
N1—C7—C8—C9 | 83.4 (2) | N2—C25—C26—C27 | −88.3 (2) |
N1—C7—C8—C17 | −96.1 (2) | N2—C25—C26—C35 | 90.5 (2) |
C18—O2—C9—C8 | 175.37 (19) | C36—O4—C27—C26 | 178.8 (2) |
C18—O2—C9—C10 | −4.2 (3) | C36—O4—C27—C28 | −1.3 (4) |
C17—C8—C9—O2 | 178.85 (16) | C35—C26—C27—O4 | −178.50 (17) |
C7—C8—C9—O2 | −0.7 (3) | C25—C26—C27—O4 | 0.3 (3) |
C17—C8—C9—C10 | −1.6 (3) | C35—C26—C27—C28 | 1.6 (3) |
C7—C8—C9—C10 | 178.88 (18) | C25—C26—C27—C28 | −179.6 (2) |
O2—C9—C10—C11 | 178.6 (2) | O4—C27—C28—C29 | 178.5 (2) |
C8—C9—C10—C11 | −0.9 (3) | C26—C27—C28—C29 | −1.6 (4) |
C9—C10—C11—C16 | 1.9 (3) | C27—C28—C29—C34 | 0.6 (4) |
C16—C12—C13—C14 | −0.6 (4) | C34—C30—C31—C32 | −0.6 (4) |
C12—C13—C14—C15 | −1.1 (4) | C30—C31—C32—C33 | 0.6 (4) |
C13—C14—C15—C17 | 1.1 (4) | C31—C32—C33—C35 | −0.1 (4) |
C10—C11—C16—C12 | 178.9 (2) | C28—C29—C34—C35 | 0.4 (4) |
C10—C11—C16—C17 | −0.2 (3) | C28—C29—C34—C30 | −179.5 (2) |
C13—C12—C16—C11 | −177.0 (2) | C31—C30—C34—C29 | 179.9 (3) |
C13—C12—C16—C17 | 2.1 (3) | C31—C30—C34—C35 | 0.1 (4) |
C14—C15—C17—C8 | 179.9 (2) | C32—C33—C35—C34 | −0.4 (3) |
C14—C15—C17—C16 | 0.5 (3) | C32—C33—C35—C26 | −179.5 (2) |
C9—C8—C17—C15 | −176.21 (18) | C29—C34—C35—C33 | −179.4 (2) |
C7—C8—C17—C15 | 3.3 (3) | C30—C34—C35—C33 | 0.4 (3) |
C9—C8—C17—C16 | 3.2 (3) | C29—C34—C35—C26 | −0.4 (3) |
C7—C8—C17—C16 | −177.29 (17) | C30—C34—C35—C26 | 179.5 (2) |
C11—C16—C17—C15 | 177.13 (18) | C27—C26—C35—C33 | 178.39 (19) |
C12—C16—C17—C15 | −2.0 (3) | C25—C26—C35—C33 | −0.4 (3) |
C11—C16—C17—C8 | −2.3 (3) | C27—C26—C35—C34 | −0.6 (3) |
C12—C16—C17—C8 | 178.50 (18) | C25—C26—C35—C34 | −179.40 (17) |
Cg1, Cg2, Cg3, Cg5 and Cg7 are the centroids of rings C1–C6, C8–C11/C16/C17, C12–C17, C19–C24 and C30–C35, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cg5i | 0.93 | 2.93 | 3.826 (3) | 162 |
C18—H18A···Cg3ii | 0.96 | 2.81 | 3.637 (3) | 144 |
C21—H21···Cg1iii | 0.93 | 2.99 | 3.890 (3) | 165 |
C24—H24···Cg2 | 0.93 | 2.97 | 3.753 (2) | 143 |
C36—H36B···Cg7iv | 0.96 | 2.98 | 3.814 (3) | 146 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+1, y, z. |
Acknowledgements
We are grateful to the Ministry of the Higher Education and Scientific Research, and the Department of Chemistry, University of Constantine1, for support for this work.
References
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kirk-Othmer (1979). Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed, pp. 309–354. New York: John Wiley. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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