3-Amino-1-(4-meth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

Asiri, A.M.; Al-Youbi, A.O.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811033617

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2449

doi:10.1107/S1600536811033617

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3-Amino-1-(4-methoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 17 August 2011; accepted 18 August 2011; online 27 August 2011)

In the title compound, C₂₃H₁₇N₃O, significant deviations from planarity are evidenced. This is quantified in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the methoxybenzene [67.93 (8)°] and 1,2-dihydronaphthalene [28.27 (8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the methoxy-O atom and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ( $[\overline{1}]$ $[\overline{1}]$ 1) plane.

Related literature

For background to the biological activity of related compounds, see: Aly et al. (1991 ); Al-Saadi et al. (2005 ); Rostom et al. (2011 ). For ring conformational analysis, see: Cremer & Pople (1975 ). For a related structure, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₂₃H₁₇N₃O
M_r = 351.40
Monoclinic, P 2₁ /c
a = 9.0212 (4) Å
b = 22.1475 (8) Å
c = 9.3114 (4) Å
β = 110.410 (5)°
V = 1743.60 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.714, T_max = 1.000
8688 measured reflections
3890 independent reflections
2953 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.116
S = 1.04
3890 reflections
252 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1ⁱ	0.89 (1)	2.21 (1)	3.0307 (19)	154 (2)
N2—H2⋯N1ⁱⁱ	0.88 (1)	2.33 (1)	3.115 (2)	149 (2)
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x-1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033617/hg5084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033617/hg5084Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033617/hg5084Isup3.cml

checkCIF report

Comment top

The study of the title compound (I) was motivated by recent reports of the biological activity of related compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011) and allied crystal structure investigations (Asiri et al., 2011).

The structure of (I), Fig. 1, is isostructural with the derivative in which the methoxybenzene group in (I) is substituted for a 2H-1,3-benzodioxol-5-yl group (Asiri et al., 2011). With respect to the amino-benzene ring, the benzene rings of the methoxybenzene and 1,2-dihydronaphthalene residues form dihedral angles of 67.93 (8) and 28.27 (8) °, respectively, indicating non-planarity in the molecule. In the 1,2-dihydronaphthalene residue, the cyclohexa-1,3-diene ring has a distorted half-chair conformation as defined by the following parameters (Cremer & Pople, 1975): q₂ = 0.5166 (18) Å, ϕ₂ = 84.4 (2) °, q₃ = 0.1891 (19) Å, and puckering amplitude Q = 0.5501 (19) Å.

In the crystal structure, supramolecular arrays with zigzag topology and running parallel to the (1 1 1) plane are formed through N—H···O(methoxy) and N—H···N(cyano) hydrogen bonding, Table 1 and Fig. 2.

Related literature top

For background to the biological activity of related compounds, see: Aly et al. (1991); Al-Saadi et al. (2005); Rostom et al. (2011). For ring conformational analysis, see: Cremer & Pople (1975). For a related structure, see: Asiri et al. (2011).

Experimental top

A mixture of the 4-anisaldehyde (1.36 g,10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool and the precipitate that formed was filtered, washed with water, dried and recrystallized from DMF; M.pt.: 487–488 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular array in (I) viewed towards the (1 1 1) plane. The N—H···O and N—H···.N hydrogen bonds are shown as orange and blue dashed lines, respectively.

3-Amino-1-(4-methoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile top

Crystal data top

C₂₃H₁₇N₃O	F(000) = 736
M_r = 351.40	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3338 reflections
a = 9.0212 (4) Å	θ = 2.3–29.3°
b = 22.1475 (8) Å	µ = 0.08 mm⁻¹
c = 9.3114 (4) Å	T = 100 K
β = 110.410 (5)°	Plate, orange
V = 1743.60 (12) Å³	0.25 × 0.25 × 0.05 mm
Z = 4

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3890 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2953 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scan	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −26→28
T_min = 0.714, T_max = 1.000	l = −12→11
8688 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0431P)² + 0.7237P] where P = (F_o² + 2F_c²)/3
3890 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.33 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₇N₃O	V = 1743.60 (12) Å³
M_r = 351.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0212 (4) Å	µ = 0.08 mm⁻¹
b = 22.1475 (8) Å	T = 100 K
c = 9.3114 (4) Å	0.25 × 0.25 × 0.05 mm
β = 110.410 (5)°

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3890 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2953 reflections with I > 2σ(I)
T_min = 0.714, T_max = 1.000	R_int = 0.030
8688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
3890 reflections	Δρ_min = −0.23 e Å⁻³
252 parameters

Special details top

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

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 > σ(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
O1	0.50780 (13)	0.32058 (5)	0.20429 (14)	0.0233 (3)
N1	−0.35267 (17)	−0.04178 (6)	0.09331 (17)	0.0253 (3)
N2	−0.31052 (17)	0.09057 (7)	−0.04975 (18)	0.0273 (4)
H1	−0.341 (2)	0.1248 (6)	−0.101 (2)	0.029 (5)*
H2	−0.383 (2)	0.0640 (8)	−0.048 (2)	0.040 (6)*
N3	−0.12484 (19)	0.22536 (7)	−0.09041 (19)	0.0348 (4)
C1	−0.11308 (18)	0.02880 (7)	0.13513 (19)	0.0181 (3)
C2	−0.15970 (18)	0.08249 (7)	0.04721 (19)	0.0191 (4)
C3	−0.04407 (19)	0.12715 (7)	0.06686 (19)	0.0194 (4)
C4	0.11146 (19)	0.11967 (8)	0.1705 (2)	0.0221 (4)
C5	0.15320 (19)	0.06722 (8)	0.2563 (2)	0.0222 (4)
C6	0.31513 (19)	0.05910 (8)	0.3770 (2)	0.0245 (4)
H6A	0.3719	0.0982	0.3975	0.029*
H6B	0.3777	0.0302	0.3403	0.029*
C7	0.2964 (2)	0.03549 (7)	0.5226 (2)	0.0221 (4)
H7A	0.4017	0.0295	0.6024	0.027*
H7B	0.2372	0.0651	0.5613	0.027*
C8	0.20844 (19)	−0.02353 (7)	0.4888 (2)	0.0201 (4)
C9	0.2469 (2)	−0.07051 (8)	0.5946 (2)	0.0219 (4)
H9	0.3289	−0.0650	0.6908	0.026*
C10	0.1678 (2)	−0.12526 (8)	0.5624 (2)	0.0235 (4)
H10	0.1918	−0.1563	0.6375	0.028*
C11	0.0535 (2)	−0.13428 (8)	0.4195 (2)	0.0242 (4)
H11	0.0014	−0.1722	0.3953	0.029*
C12	0.01471 (19)	−0.08839 (7)	0.3118 (2)	0.0213 (4)
H12	−0.0623	−0.0955	0.2134	0.026*
C13	0.08722 (18)	−0.03175 (7)	0.34554 (19)	0.0182 (3)
C14	0.04050 (18)	0.02098 (7)	0.24062 (19)	0.0183 (3)
C15	−0.24040 (19)	−0.01280 (7)	0.11644 (19)	0.0206 (4)
C16	−0.0873 (2)	0.18193 (8)	−0.0198 (2)	0.0235 (4)
C17	0.22517 (18)	0.17059 (7)	0.18816 (19)	0.0198 (4)
C18	0.20113 (19)	0.22527 (8)	0.25000 (19)	0.0219 (4)
H18	0.1168	0.2292	0.2884	0.026*
C19	0.29915 (19)	0.27411 (8)	0.25614 (19)	0.0200 (4)
H19	0.2823	0.3112	0.2993	0.024*
C20	0.42161 (18)	0.26902 (7)	0.19956 (18)	0.0186 (3)
C21	0.45114 (19)	0.21406 (8)	0.14320 (19)	0.0215 (4)
H21	0.5378	0.2098	0.1084	0.026*
C22	0.35293 (19)	0.16540 (8)	0.13821 (19)	0.0217 (4)
H22	0.3733	0.1277	0.0999	0.026*
C23	0.5989 (2)	0.32247 (8)	0.1054 (2)	0.0254 (4)
H23A	0.6552	0.3611	0.1186	0.038*
H23B	0.5283	0.3184	−0.0013	0.038*
H23C	0.6755	0.2893	0.1314	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0230 (6)	0.0200 (6)	0.0264 (7)	−0.0091 (5)	0.0079 (5)	−0.0019 (5)
N1	0.0189 (7)	0.0213 (8)	0.0318 (8)	−0.0017 (6)	0.0039 (6)	0.0000 (6)
N2	0.0174 (7)	0.0234 (8)	0.0343 (9)	−0.0044 (6)	0.0004 (7)	0.0086 (7)
N3	0.0357 (9)	0.0216 (8)	0.0331 (9)	−0.0061 (7)	−0.0056 (7)	0.0032 (7)
C1	0.0162 (8)	0.0153 (8)	0.0234 (8)	−0.0010 (6)	0.0078 (7)	−0.0013 (6)
C2	0.0171 (8)	0.0200 (8)	0.0202 (8)	−0.0002 (7)	0.0063 (7)	−0.0007 (7)
C3	0.0189 (8)	0.0161 (8)	0.0216 (8)	−0.0005 (6)	0.0052 (7)	0.0010 (6)
C4	0.0192 (8)	0.0194 (9)	0.0263 (9)	−0.0033 (7)	0.0061 (7)	0.0005 (7)
C5	0.0162 (8)	0.0229 (9)	0.0257 (9)	−0.0003 (7)	0.0050 (7)	0.0033 (7)
C6	0.0146 (8)	0.0218 (9)	0.0339 (10)	−0.0008 (7)	0.0043 (7)	0.0060 (8)
C7	0.0179 (8)	0.0183 (8)	0.0268 (9)	0.0009 (7)	0.0036 (7)	0.0005 (7)
C8	0.0170 (8)	0.0184 (8)	0.0268 (9)	0.0033 (7)	0.0101 (7)	0.0003 (7)
C9	0.0205 (8)	0.0222 (9)	0.0235 (9)	0.0052 (7)	0.0083 (7)	0.0009 (7)
C10	0.0245 (9)	0.0181 (9)	0.0306 (10)	0.0049 (7)	0.0130 (8)	0.0060 (7)
C11	0.0198 (8)	0.0162 (8)	0.0377 (10)	0.0015 (7)	0.0114 (8)	0.0026 (7)
C12	0.0156 (8)	0.0200 (9)	0.0278 (9)	0.0017 (7)	0.0071 (7)	0.0006 (7)
C13	0.0140 (7)	0.0153 (8)	0.0266 (9)	0.0034 (6)	0.0090 (7)	0.0023 (7)
C14	0.0173 (8)	0.0164 (8)	0.0224 (8)	0.0014 (6)	0.0083 (7)	0.0004 (7)
C15	0.0194 (8)	0.0186 (8)	0.0220 (9)	0.0039 (7)	0.0049 (7)	0.0016 (7)
C16	0.0193 (8)	0.0200 (9)	0.0251 (9)	−0.0059 (7)	0.0001 (7)	−0.0024 (7)
C17	0.0160 (8)	0.0184 (8)	0.0202 (8)	−0.0019 (7)	0.0002 (7)	0.0034 (7)
C18	0.0174 (8)	0.0254 (9)	0.0214 (9)	−0.0015 (7)	0.0050 (7)	0.0027 (7)
C19	0.0193 (8)	0.0191 (8)	0.0191 (8)	−0.0005 (7)	0.0037 (7)	−0.0025 (7)
C20	0.0166 (8)	0.0189 (8)	0.0165 (8)	−0.0049 (7)	0.0013 (6)	0.0013 (6)
C21	0.0194 (8)	0.0248 (9)	0.0200 (8)	−0.0015 (7)	0.0065 (7)	0.0002 (7)
C22	0.0229 (8)	0.0171 (8)	0.0228 (9)	0.0002 (7)	0.0049 (7)	−0.0011 (7)
C23	0.0219 (9)	0.0271 (10)	0.0261 (9)	−0.0061 (7)	0.0072 (7)	0.0052 (7)

Geometric parameters (Å, º) top

O1—C20	1.3735 (19)	C8—C13	1.411 (2)
O1—C23	1.433 (2)	C9—C10	1.386 (2)
N1—C15	1.154 (2)	C9—H9	0.9500
N2—C2	1.357 (2)	C10—C11	1.384 (2)
N2—H1	0.889 (9)	C10—H10	0.9500
N2—H2	0.883 (9)	C11—C12	1.385 (2)
N3—C16	1.147 (2)	C11—H11	0.9500
C1—C14	1.402 (2)	C12—C13	1.399 (2)
C1—C2	1.421 (2)	C12—H12	0.9500
C1—C15	1.435 (2)	C13—C14	1.486 (2)
C2—C3	1.402 (2)	C17—C22	1.390 (2)
C3—C4	1.408 (2)	C17—C18	1.390 (2)
C3—C16	1.434 (2)	C18—C19	1.385 (2)
C4—C5	1.385 (2)	C18—H18	0.9500
C4—C17	1.494 (2)	C19—C20	1.384 (2)
C5—C14	1.414 (2)	C19—H19	0.9500
C5—C6	1.512 (2)	C20—C21	1.388 (2)
C6—C7	1.517 (2)	C21—C22	1.386 (2)
C6—H6A	0.9900	C21—H21	0.9500
C6—H6B	0.9900	C22—H22	0.9500
C7—C8	1.504 (2)	C23—H23A	0.9800
C7—H7A	0.9900	C23—H23B	0.9800
C7—H7B	0.9900	C23—H23C	0.9800
C8—C9	1.391 (2)

C20—O1—C23	116.67 (13)	C9—C10—H10	120.3
C2—N2—H1	121.6 (13)	C10—C11—C12	120.38 (16)
C2—N2—H2	118.4 (14)	C10—C11—H11	119.8
H1—N2—H2	119.1 (19)	C12—C11—H11	119.8
C14—C1—C2	121.91 (14)	C11—C12—C13	121.00 (16)
C14—C1—C15	124.01 (15)	C11—C12—H12	119.5
C2—C1—C15	113.81 (14)	C13—C12—H12	119.5
N2—C2—C3	121.41 (15)	C12—C13—C8	118.40 (15)
N2—C2—C1	121.35 (15)	C12—C13—C14	123.62 (15)
C3—C2—C1	117.23 (14)	C8—C13—C14	117.96 (14)
C2—C3—C4	121.63 (15)	C1—C14—C5	118.82 (15)
C2—C3—C16	118.66 (15)	C1—C14—C13	122.83 (14)
C4—C3—C16	119.70 (15)	C5—C14—C13	118.19 (14)
C5—C4—C3	119.95 (15)	N1—C15—C1	173.19 (17)
C5—C4—C17	122.08 (15)	N3—C16—C3	178.65 (19)
C3—C4—C17	117.93 (15)	C22—C17—C18	118.55 (15)
C4—C5—C14	120.44 (15)	C22—C17—C4	121.21 (15)
C4—C5—C6	121.76 (15)	C18—C17—C4	120.19 (15)
C14—C5—C6	117.65 (15)	C19—C18—C17	120.51 (15)
C5—C6—C7	109.01 (14)	C19—C18—H18	119.7
C5—C6—H6A	109.9	C17—C18—H18	119.7
C7—C6—H6A	109.9	C20—C19—C18	120.22 (15)
C5—C6—H6B	109.9	C20—C19—H19	119.9
C7—C6—H6B	109.9	C18—C19—H19	119.9
H6A—C6—H6B	108.3	O1—C20—C19	115.98 (14)
C8—C7—C6	109.13 (14)	O1—C20—C21	124.07 (15)
C8—C7—H7A	109.9	C19—C20—C21	119.94 (15)
C6—C7—H7A	109.9	C22—C21—C20	119.35 (15)
C8—C7—H7B	109.9	C22—C21—H21	120.3
C6—C7—H7B	109.9	C20—C21—H21	120.3
H7A—C7—H7B	108.3	C21—C22—C17	121.31 (15)
C9—C8—C13	119.53 (15)	C21—C22—H22	119.3
C9—C8—C7	121.24 (15)	C17—C22—H22	119.3
C13—C8—C7	119.21 (15)	O1—C23—H23A	109.5
C10—C9—C8	121.23 (16)	O1—C23—H23B	109.5
C10—C9—H9	119.4	H23A—C23—H23B	109.5
C8—C9—H9	119.4	O1—C23—H23C	109.5
C11—C10—C9	119.31 (16)	H23A—C23—H23C	109.5
C11—C10—H10	120.3	H23B—C23—H23C	109.5

C14—C1—C2—N2	−177.16 (16)	C9—C8—C13—C14	175.09 (14)
C15—C1—C2—N2	−3.0 (2)	C7—C8—C13—C14	−6.4 (2)
C14—C1—C2—C3	1.8 (2)	C2—C1—C14—C5	−1.9 (2)
C15—C1—C2—C3	175.94 (15)	C15—C1—C14—C5	−175.51 (15)
N2—C2—C3—C4	178.21 (17)	C2—C1—C14—C13	173.29 (15)
C1—C2—C3—C4	−0.7 (2)	C15—C1—C14—C13	−0.3 (3)
N2—C2—C3—C16	−0.9 (3)	C4—C5—C14—C1	1.0 (2)
C1—C2—C3—C16	−179.86 (15)	C6—C5—C14—C1	176.69 (15)
C2—C3—C4—C5	−0.1 (3)	C4—C5—C14—C13	−174.42 (16)
C16—C3—C4—C5	179.01 (16)	C6—C5—C14—C13	1.3 (2)
C2—C3—C4—C17	−177.76 (15)	C12—C13—C14—C1	28.1 (2)
C16—C3—C4—C17	1.4 (2)	C8—C13—C14—C1	−150.04 (16)
C3—C4—C5—C14	0.0 (3)	C12—C13—C14—C5	−156.66 (16)
C17—C4—C5—C14	177.51 (16)	C8—C13—C14—C5	25.2 (2)
C3—C4—C5—C6	−175.50 (16)	C5—C4—C17—C22	70.5 (2)
C17—C4—C5—C6	2.0 (3)	C3—C4—C17—C22	−111.93 (18)
C4—C5—C6—C7	132.25 (17)	C5—C4—C17—C18	−112.04 (19)
C14—C5—C6—C7	−43.4 (2)	C3—C4—C17—C18	65.5 (2)
C5—C6—C7—C8	58.90 (18)	C22—C17—C18—C19	2.4 (2)
C6—C7—C8—C9	142.75 (15)	C4—C17—C18—C19	−175.12 (15)
C6—C7—C8—C13	−35.7 (2)	C17—C18—C19—C20	0.5 (2)
C13—C8—C9—C10	−0.3 (2)	C23—O1—C20—C19	−160.73 (14)
C7—C8—C9—C10	−178.80 (15)	C23—O1—C20—C21	19.5 (2)
C8—C9—C10—C11	3.0 (2)	C18—C19—C20—O1	177.14 (14)
C9—C10—C11—C12	−2.2 (2)	C18—C19—C20—C21	−3.1 (2)
C10—C11—C12—C13	−1.4 (2)	O1—C20—C21—C22	−177.48 (15)
C11—C12—C13—C8	4.0 (2)	C19—C20—C21—C22	2.8 (2)
C11—C12—C13—C14	−174.11 (15)	C20—C21—C22—C17	0.2 (2)
C9—C8—C13—C12	−3.2 (2)	C18—C17—C22—C21	−2.7 (2)
C7—C8—C13—C12	175.35 (15)	C4—C17—C22—C21	174.76 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1ⁱ	0.89 (1)	2.21 (1)	3.0307 (19)	154 (2)
N2—H2···N1ⁱⁱ	0.88 (1)	2.33 (1)	3.115 (2)	149 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O
M_r	351.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0212 (4), 22.1475 (8), 9.3114 (4)
β (°)	110.410 (5)
V (Å³)	1743.60 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.714, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8688, 3890, 2953
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.116, 1.04
No. of reflections	3890
No. of parameters	252
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1ⁱ	0.889 (9)	2.207 (12)	3.0307 (19)	153.9 (17)
N2—H2···N1ⁱⁱ	0.883 (9)	2.326 (14)	3.115 (2)	148.8 (18)

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

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