Ethyl 4-anilino-2-methyl-5-oxo-1-phenyl-2,5-di­hydro-1H-pyrrole-2-carboxyl­ate

Akkurt, M.; Mohamed, S.K.; Elremaily, M.A.A.; Santoyo-Gonzalez, F.; Albayati, M.R.

doi:10.1107/S1600536813030390

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1757-o1758

doi:10.1107/S1600536813030390

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Ethyl 4-anilino-2-methyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylate

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c Mahmoud A. A. Elremaily,^d,^e Francisco Santoyo-Gonzalez ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, ^eDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada E-18071, Spain, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 4 November 2013; accepted 6 November 2013; online 9 November 2013)

In the title compound, C₂₀H₂₀N₂O₃, the central 2,5-dihydro-1H-pyrrole ring [r.m.s. deviation = 0.014 (1) Å] is oriented at dihedral angles of 77.81 (6) and 25.33 (6)°, respectively, to the attached phenyl ring and the aniline phenyl ring. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked through pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R₂²(10) ring motif. Two weak C—H⋯π interactions are also observed.

CCDC reference: 970430

Related literature

For the synthesis of pyrrolone compounds, see: Shiraki et al. (1996 ). For the biological activity of lactams, see: Alvi et al. (1998 ); Li et al. (2002 ); Mase et al. (1999 ); Wiedhopf et al. (1973 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₀N₂O₃
M_r = 336.38
Triclinic, $[P \overline 1]$
a = 5.9071 (6) Å
b = 11.3474 (12) Å
c = 14.1716 (14) Å
α = 111.467 (2)°
β = 101.113 (3)°
γ = 95.328 (3)°
V = 853.45 (15) Å³
Z = 2
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.34 × 0.29 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.783, T_max = 0.860
18887 measured reflections
3367 independent reflections
3156 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.04
3367 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C8–C13 and C15–C20 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.898 (17)	2.443 (16)	2.8247 (14)	105.9 (12)
N2—H2N⋯O3ⁱ	0.898 (17)	2.033 (17)	2.9135 (14)	166.3 (14)
C1—H1B⋯Cg2ⁱⁱ	0.98	2.91	3.6177 (15)	130
C12—H12⋯Cg3ⁱⁱⁱ	0.95	2.84	3.4865 (14)	126
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 970430

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813030390/is5318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030390/is5318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030390/is5318Isup3.cml

checkCIF report

Comment top

Dihydropyrrolone compounds have been reported to display importantant biological activities with better hydrolytic stability. Dihydropyrrolones are known as lactams such as Pulchellalactam, which inhibits CD45 protein, a receptor-like transmembrane protein tyrosine phosphatase, and therefore could be of therapeutic value targeting autoimmune and chronic anti-inflammatory diseases (Alvi et al., 1998; Li et al., 2002). γ-Lactam PI-091 has been reported to display potent activity against platelet aggregation (Shiraki et al., 1996) and jatropham has been proven to be an antitumor alkaloid (Mase et al., 1999; Wiedhopf et al., 1973). Numerous methods to synthesize pyrrol-2-ones have been reported in the literature and the majority of these require multiple steps with low yields. However, one direct conversion strategy has been demonstrated in synthesis of γ-lactam PI-091 (Shiraki et al., 1996). Based on this concept, we herein report the synthesis and crystal structure of the title compound.

In the title compound, the central 2,5-dihydro-1H-pyrrole ring (N1/C4–C7) makes dihedral angles of 77.81 (6) and 25.33 (6)° with the two phenyl rings (C8–C13 and C15–C20), respectively (Fig. 1). All bond lengths and bond angles are normal (Allen et al., 1987).

In the crystal structure, pairs of adjacent molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming inversion dimers with R²₂(10) ring motifs (Bernstein et al., 1995; Fig. 2). Two weak C—H···π interactions are observed.

Related literature top

For the synthesis of pyrrolone compounds, see: Shiraki et al. (1996). For the biological activity of lactams, see: Alvi et al. (1998); Li et al. (2002); Mase et al. (1999); Wiedhopf et al. (1973). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

In a 50 ml round bottom flask, a mixture of 186 mg of aniline (2 mmol) and 232 mg of ethyl pyruvate (2 mmol) were taken in presence of 8 mol % of Fe₃O₄ nanoparticles in 15 ml ethanol/water (v/v) or glacial acetic acid was stirred well and irradited in microwave for 30 minutes. The progress of the reaction was monitored by TLC. After completion, the solid product was filtered off, washed with water and recrystallized from ethanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation method of an ethanolic solution of the title compound at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the molecular packing and hydrogen bonding (dotted lines) of the title compound along the a axis. H atoms not involved in H bonding are omitted for clarity.

Ethyl 4-anilino-2-methyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylate top

Crystal data top

C₂₀H₂₀N₂O₃	Z = 2
M_r = 336.38	F(000) = 356
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.9071 (6) Å	Cell parameters from 9891 reflections
b = 11.3474 (12) Å	θ = 3.5–72.5°
c = 14.1716 (14) Å	µ = 0.72 mm⁻¹
α = 111.467 (2)°	T = 100 K
β = 101.113 (3)°	Cubs, colourless
γ = 95.328 (3)°	0.34 × 0.29 × 0.21 mm
V = 853.45 (15) Å³

Data collection top

Bruker APEXII CCD diffractometer	3367 independent reflections
Radiation source: sealed tube	3156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 72.6°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.783, T_max = 0.860	k = −14→14
18887 measured reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0487P)² + 0.3108P] WHERE P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.32 e Å⁻³
3367 reflections	Δρ_min = −0.17 e Å⁻³
232 parameters

Crystal data top

C₂₀H₂₀N₂O₃	γ = 95.328 (3)°
M_r = 336.38	V = 853.45 (15) Å³
Triclinic, P1	Z = 2
a = 5.9071 (6) Å	Cu Kα radiation
b = 11.3474 (12) Å	µ = 0.72 mm⁻¹
c = 14.1716 (14) Å	T = 100 K
α = 111.467 (2)°	0.34 × 0.29 × 0.21 mm
β = 101.113 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3156 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.860	R_int = 0.035
18887 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.32 e Å⁻³
3367 reflections	Δρ_min = −0.17 e Å⁻³
232 parameters

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 e.s.d.'s 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 > σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.25546 (15)	0.15386 (9)	0.65884 (6)	0.0278 (3)
O2	0.56211 (15)	0.05034 (9)	0.64918 (7)	0.0284 (3)
O3	0.76449 (14)	−0.06561 (7)	0.91641 (6)	0.0245 (2)
N1	0.46752 (16)	−0.03089 (9)	0.80378 (7)	0.0188 (2)
N2	0.88879 (16)	0.20496 (9)	1.01844 (7)	0.0198 (3)
C1	0.0420 (2)	0.20985 (14)	0.52705 (10)	0.0347 (4)
C2	0.2691 (2)	0.17212 (13)	0.56318 (10)	0.0321 (4)
C3	0.41016 (19)	0.09001 (10)	0.69110 (8)	0.0202 (3)
C4	0.37187 (18)	0.07904 (10)	0.79249 (8)	0.0185 (3)
C5	0.53286 (19)	0.19157 (10)	0.88320 (8)	0.0186 (3)
C6	0.69734 (18)	0.14945 (10)	0.93602 (8)	0.0174 (3)
C7	0.65363 (18)	0.00576 (10)	0.88708 (8)	0.0179 (3)
C8	0.38731 (19)	−0.16263 (10)	0.73392 (8)	0.0195 (3)
C9	0.5140 (2)	−0.22001 (12)	0.66212 (11)	0.0326 (4)
C10	0.4452 (2)	−0.34902 (13)	0.59739 (12)	0.0386 (4)
C11	0.2505 (2)	−0.42071 (11)	0.60400 (10)	0.0279 (3)
C12	0.1241 (2)	−0.36303 (11)	0.67556 (9)	0.0262 (3)
C13	0.1920 (2)	−0.23334 (11)	0.74107 (9)	0.0241 (3)
C14	0.11531 (19)	0.07087 (11)	0.79771 (9)	0.0235 (3)
C15	0.97223 (19)	0.33611 (10)	1.07830 (8)	0.0189 (3)
C16	1.2078 (2)	0.37409 (11)	1.13371 (9)	0.0229 (3)
C17	1.2957 (2)	0.50213 (12)	1.19811 (10)	0.0258 (3)
C18	1.1522 (2)	0.59446 (11)	1.20871 (10)	0.0263 (3)
C19	0.9195 (2)	0.55647 (11)	1.15397 (10)	0.0273 (3)
C20	0.8280 (2)	0.42848 (11)	1.08897 (9)	0.0233 (3)
H1A	−0.08820	0.14030	0.51190	0.0520*
H1B	0.04340	0.22560	0.46360	0.0520*
H1C	0.02220	0.28840	0.58200	0.0520*
H2A	0.28960	0.09150	0.50930	0.0390*
H2B	0.40280	0.24060	0.57730	0.0390*
H2N	0.981 (3)	0.1504 (14)	1.0297 (11)	0.025 (3)*
H5	0.51940	0.27930	0.90030	0.0220*
H9	0.64740	−0.17100	0.65730	0.0390*
H10	0.53200	−0.38860	0.54820	0.0460*
H11	0.20380	−0.50930	0.55940	0.0340*
H12	−0.00960	−0.41220	0.68000	0.0310*
H13	0.10520	−0.19370	0.79020	0.0290*
H14A	0.01820	0.00030	0.73480	0.0350*
H14B	0.06470	0.15210	0.80210	0.0350*
H14C	0.09850	0.05490	0.85970	0.0350*
H16	1.30760	0.31200	1.12720	0.0270*
H17	1.45580	0.52720	1.23550	0.0310*
H18	1.21320	0.68220	1.25280	0.0320*
H19	0.82040	0.61890	1.16090	0.0330*
H20	0.66770	0.40400	1.05190	0.0280*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0344 (5)	0.0343 (5)	0.0224 (4)	0.0158 (4)	0.0085 (4)	0.0168 (4)
O2	0.0282 (4)	0.0362 (5)	0.0246 (4)	0.0117 (4)	0.0100 (3)	0.0131 (4)
O3	0.0252 (4)	0.0189 (4)	0.0263 (4)	0.0053 (3)	−0.0017 (3)	0.0091 (3)
N1	0.0187 (4)	0.0161 (4)	0.0194 (4)	0.0038 (3)	0.0006 (4)	0.0064 (4)
N2	0.0209 (5)	0.0171 (4)	0.0189 (5)	0.0058 (4)	0.0009 (4)	0.0057 (4)
C1	0.0423 (8)	0.0358 (7)	0.0282 (6)	0.0081 (6)	0.0000 (6)	0.0190 (6)
C2	0.0427 (7)	0.0380 (7)	0.0222 (6)	0.0129 (6)	0.0085 (5)	0.0176 (5)
C3	0.0206 (5)	0.0180 (5)	0.0183 (5)	0.0022 (4)	0.0009 (4)	0.0053 (4)
C4	0.0191 (5)	0.0172 (5)	0.0192 (5)	0.0051 (4)	0.0031 (4)	0.0074 (4)
C5	0.0210 (5)	0.0162 (5)	0.0178 (5)	0.0041 (4)	0.0048 (4)	0.0057 (4)
C6	0.0188 (5)	0.0170 (5)	0.0165 (5)	0.0036 (4)	0.0059 (4)	0.0057 (4)
C7	0.0177 (5)	0.0184 (5)	0.0178 (5)	0.0038 (4)	0.0048 (4)	0.0069 (4)
C8	0.0199 (5)	0.0171 (5)	0.0191 (5)	0.0033 (4)	−0.0004 (4)	0.0069 (4)
C9	0.0248 (6)	0.0221 (6)	0.0442 (8)	0.0011 (5)	0.0142 (5)	0.0034 (5)
C10	0.0354 (7)	0.0237 (6)	0.0481 (8)	0.0039 (5)	0.0205 (6)	−0.0003 (6)
C11	0.0303 (6)	0.0177 (5)	0.0285 (6)	0.0010 (5)	0.0018 (5)	0.0043 (5)
C12	0.0291 (6)	0.0229 (6)	0.0245 (6)	−0.0031 (5)	0.0035 (5)	0.0104 (5)
C13	0.0298 (6)	0.0232 (6)	0.0197 (5)	0.0022 (5)	0.0065 (5)	0.0092 (5)
C14	0.0189 (5)	0.0255 (6)	0.0277 (6)	0.0056 (4)	0.0056 (4)	0.0121 (5)
C15	0.0225 (5)	0.0175 (5)	0.0166 (5)	0.0032 (4)	0.0052 (4)	0.0066 (4)
C16	0.0217 (5)	0.0221 (6)	0.0242 (6)	0.0055 (4)	0.0051 (4)	0.0081 (5)
C17	0.0211 (5)	0.0247 (6)	0.0275 (6)	−0.0004 (4)	0.0036 (5)	0.0080 (5)
C18	0.0302 (6)	0.0174 (5)	0.0271 (6)	−0.0003 (5)	0.0055 (5)	0.0059 (5)
C19	0.0302 (6)	0.0191 (6)	0.0306 (6)	0.0077 (5)	0.0056 (5)	0.0076 (5)
C20	0.0219 (5)	0.0207 (6)	0.0238 (6)	0.0048 (4)	0.0024 (4)	0.0063 (5)

Geometric parameters (Å, º) top

O1—C2	1.4601 (16)	C16—C17	1.3857 (19)
O1—C3	1.3317 (15)	C17—C18	1.3920 (19)
O2—C3	1.2025 (15)	C18—C19	1.3825 (18)
O3—C7	1.2237 (14)	C19—C20	1.3904 (18)
N1—C4	1.4639 (16)	C1—H1A	0.9800
N1—C7	1.3530 (14)	C1—H1B	0.9800
N1—C8	1.4296 (15)	C1—H1C	0.9800
N2—C6	1.3638 (14)	C2—H2A	0.9900
N2—C15	1.3985 (16)	C2—H2B	0.9900
N2—H2N	0.898 (17)	C5—H5	0.9500
C1—C2	1.4991 (19)	C9—H9	0.9500
C3—C4	1.5434 (15)	C10—H10	0.9500
C4—C5	1.5130 (16)	C11—H11	0.9500
C4—C14	1.5274 (16)	C12—H12	0.9500
C5—C6	1.3418 (16)	C13—H13	0.9500
C6—C7	1.4938 (17)	C14—H14A	0.9800
C8—C9	1.3851 (17)	C14—H14B	0.9800
C8—C13	1.3848 (17)	C14—H14C	0.9800
C9—C10	1.383 (2)	C16—H16	0.9500
C10—C11	1.3845 (19)	C17—H17	0.9500
C11—C12	1.3825 (17)	C18—H18	0.9500
C12—C13	1.3912 (18)	C19—H19	0.9500
C15—C20	1.3953 (17)	C20—H20	0.9500
C15—C16	1.3994 (16)

C2—O1—C3	116.61 (9)	C2—C1—H1A	110.00
C4—N1—C7	112.22 (10)	C2—C1—H1B	109.00
C4—N1—C8	125.67 (9)	C2—C1—H1C	109.00
C7—N1—C8	122.05 (10)	H1A—C1—H1B	109.00
C6—N2—C15	127.95 (10)	H1A—C1—H1C	109.00
C15—N2—H2N	116.7 (10)	H1B—C1—H1C	109.00
C6—N2—H2N	114.9 (10)	O1—C2—H2A	111.00
O1—C2—C1	106.07 (10)	O1—C2—H2B	111.00
O1—C3—O2	124.92 (11)	C1—C2—H2A	110.00
O2—C3—C4	125.00 (11)	C1—C2—H2B	111.00
O1—C3—C4	110.04 (9)	H2A—C2—H2B	109.00
N1—C4—C14	111.56 (10)	C4—C5—H5	125.00
C3—C4—C5	107.20 (9)	C6—C5—H5	125.00
N1—C4—C5	102.09 (9)	C8—C9—H9	120.00
C5—C4—C14	113.07 (9)	C10—C9—H9	120.00
C3—C4—C14	112.87 (9)	C9—C10—H10	120.00
N1—C4—C3	109.43 (9)	C11—C10—H10	120.00
C4—C5—C6	110.17 (10)	C10—C11—H11	120.00
C5—C6—C7	108.54 (9)	C12—C11—H11	120.00
N2—C6—C5	135.95 (11)	C11—C12—H12	120.00
N2—C6—C7	115.49 (10)	C13—C12—H12	120.00
O3—C7—N1	126.32 (11)	C8—C13—H13	120.00
O3—C7—C6	126.75 (10)	C12—C13—H13	120.00
N1—C7—C6	106.93 (10)	C4—C14—H14A	109.00
N1—C8—C9	118.96 (11)	C4—C14—H14B	109.00
C9—C8—C13	120.50 (11)	C4—C14—H14C	109.00
N1—C8—C13	120.48 (10)	H14A—C14—H14B	110.00
C8—C9—C10	119.68 (12)	H14A—C14—H14C	109.00
C9—C10—C11	120.31 (12)	H14B—C14—H14C	109.00
C10—C11—C12	119.85 (13)	C15—C16—H16	120.00
C11—C12—C13	120.27 (12)	C17—C16—H16	120.00
C8—C13—C12	119.38 (11)	C16—C17—H17	120.00
N2—C15—C16	117.97 (11)	C18—C17—H17	120.00
C16—C15—C20	119.22 (11)	C17—C18—H18	121.00
N2—C15—C20	122.73 (10)	C19—C18—H18	121.00
C15—C16—C17	120.08 (12)	C18—C19—H19	119.00
C16—C17—C18	120.79 (11)	C20—C19—H19	119.00
C17—C18—C19	118.93 (12)	C15—C20—H20	120.00
C18—C19—C20	121.14 (12)	C19—C20—H20	120.00
C15—C20—C19	119.84 (11)

C3—O1—C2—C1	163.94 (11)	O2—C3—C4—N1	−25.34 (16)
C2—O1—C3—O2	2.26 (18)	C3—C4—C5—C6	−113.96 (11)
C2—O1—C3—C4	−179.93 (10)	C14—C4—C5—C6	121.00 (11)
C7—N1—C8—C13	101.78 (13)	N1—C4—C5—C6	1.02 (12)
C7—N1—C4—C5	0.49 (12)	C4—C5—C6—N2	176.18 (12)
C8—N1—C4—C5	−176.44 (10)	C4—C5—C6—C7	−2.01 (13)
C7—N1—C4—C14	−120.55 (10)	C5—C6—C7—O3	−177.72 (11)
C8—N1—C4—C14	62.53 (13)	N2—C6—C7—N1	−176.31 (9)
C4—N1—C8—C9	101.29 (14)	C5—C6—C7—N1	2.30 (12)
C7—N1—C4—C3	113.83 (10)	N2—C6—C7—O3	3.68 (17)
C8—N1—C4—C3	−63.10 (13)	N1—C8—C9—C10	176.91 (12)
C4—N1—C7—C6	−1.65 (12)	C9—C8—C13—C12	0.19 (18)
C4—N1—C7—O3	178.36 (11)	C13—C8—C9—C10	−0.23 (19)
C8—N1—C7—O3	−4.58 (18)	N1—C8—C13—C12	−176.91 (11)
C4—N1—C8—C13	−81.57 (14)	C8—C9—C10—C11	0.1 (2)
C8—N1—C7—C6	175.41 (9)	C9—C10—C11—C12	0.1 (2)
C7—N1—C8—C9	−75.36 (15)	C10—C11—C12—C13	−0.12 (19)
C15—N2—C6—C7	179.61 (10)	C11—C12—C13—C8	−0.02 (19)
C6—N2—C15—C16	−158.37 (11)	N2—C15—C16—C17	−176.86 (11)
C15—N2—C6—C5	1.5 (2)	C20—C15—C16—C17	−0.13 (18)
C6—N2—C15—C20	25.02 (18)	N2—C15—C20—C19	176.70 (11)
O1—C3—C4—C5	−93.17 (11)	C16—C15—C20—C19	0.13 (17)
O1—C3—C4—N1	156.85 (9)	C15—C16—C17—C18	0.00 (19)
O2—C3—C4—C14	−150.20 (12)	C16—C17—C18—C19	0.1 (2)
O1—C3—C4—C14	31.99 (13)	C17—C18—C19—C20	−0.1 (2)
O2—C3—C4—C5	84.64 (14)	C18—C19—C20—C15	0.00 (19)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C8–C13 and C15–C20 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.898 (17)	2.443 (16)	2.8247 (14)	105.9 (12)
N2—H2N···O3ⁱ	0.898 (17)	2.033 (17)	2.9135 (14)	166.3 (14)
C1—H1B···Cg2ⁱⁱ	0.98	2.91	3.6177 (15)	130
C12—H12···Cg3ⁱⁱⁱ	0.95	2.84	3.4865 (14)	126

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C8–C13 and C15–C20 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.898 (17)	2.443 (16)	2.8247 (14)	105.9 (12)
N2—H2N···O3ⁱ	0.898 (17)	2.033 (17)	2.9135 (14)	166.3 (14)
C1—H1B···Cg2ⁱⁱ	0.98	2.91	3.6177 (15)	130
C12—H12···Cg3ⁱⁱⁱ	0.95	2.84	3.4865 (14)	126

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

Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

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Volume 69| Part 12| December 2013| Pages o1757-o1758

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