Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxyl­ate

Jiao, Y.-H.; Zhang, Q.; Meng, F.-Y.; Teng, L.; Yuan, J.; Ng, S.W.

doi:10.1107/S1600536809008885

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o775

doi:10.1107/S1600536809008885

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Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate

Yuan-Hong Jiao,^a Qian Zhang,^a ^* Fa-Yan Meng,^a Lei Teng,^a Jia Yuan ^a and Seik Weng Ng ^b

^aSchool of Chemistry and Material Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: jiaoyuanhong1995@yahoo.com.cn

(Received 5 March 2009; accepted 11 March 2009; online 14 March 2009)

The pyranyl ring of the title compound, C₂₂H₁₉NO₃, adopts a flattened-boat conformation. The dihedral angle between naphthalene and phenyl rings is 78.3 (1)°The molecule also features an intramolecular N—H⋯O_carbonyl hydrogen bond. Adjacent molecules are linked by an intermolecular N—H⋯O_carbonyl hydrogen bond, forming a zigzag chain that runs along the c axis.

Related literature

For the crystal structures of other ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives, see: Klokol et al. (1987 ); Shi et al. (2003a ,b ); Wang et al. (2003 ); Zhuang et al. (2003a ,b ).

Experimental

Crystal data

C₂₂H₁₉NO₃
M_r = 345.38
Monoclinic, C c
a = 13.7835 (5) Å
b = 14.6460 (4) Å
c = 8.8713 (2) Å
β = 99.551 (1)°
V = 1766.05 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 K
0.36 × 0.25 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.864, T_max = 0.988
8563 measured reflections
2029 independent reflections
1958 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.078
S = 1.09
2029 reflections
244 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O3ⁱ	0.88 (1)	2.05 (1)	2.907 (2)	166 (2)
N1—H12⋯O3	0.88 (1)	2.07 (2)	2.707 (2)	129 (2)
Symmetry code: (i) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008885/zl2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008885/zl2186Isup2.hkl

checkCIF report

Comment top

2-Naphthol, substituted benzaldehydes and ethyl 2-cyanoacetate react in the presence of a catalyst to form the ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylates; the compounds possess a primary amine group. The crystal structures of several 1-aryl derivatives have been reported (Klokol et al., 1987; Shi et al., 2003a; Shi et al., 2003b; Wang et al., 2003; Zhuang et al., 2003a; Zhuang et al., 2003b). Interestingly, the crystal structure of the unsubstituted 1-phenyl compound was not known, and its structure is reported here. The title compound (Scheme I, Fig. 1) exhibits a pyranyl ring in a flattened boat conformation. The molecule also features an intramolecular N–H···O_carbonyl bond. Adjacent molecules are linked by an intermolecular N—H···O_carbonyl hydrogen bond to furnish a zigzag chain that runs along the c-axis.

Related literature top

For the crystal structures of other ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives, see: Klokol et al. (1987); Shi et al. (2003a,b); Wang et al. (2003); Zhuang et al. (2003a,b).

Experimental top

2-Naphthol (1.4 g, 10 mmol), benzaldehyde (1.1 g, 10 mmol), ethyl 2-cyanoacetate (1.0 g, 10 mmol) and piperidine (1 ml) were dissolved in ethanol (30 ml). The solution was heated for 5 h. The solvent was removed under reduced pressure and and the residue recrystallized from dichloromethane/methanol (1:1/v:v) to give yellow crystals in 80% yield; m.p. 436–437 K.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₂H₁₉NO₃; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius.
	Fig. 2. Thermal ellipsoid plot (Barbour, 2001) showing the intra and intermolecular hydrogen bonding interactions (dashed lines); displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius.

Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate top

Crystal data top

C₂₂H₁₉NO₃	F(000) = 728
M_r = 345.38	D_x = 1.299 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 8058 reflections
a = 13.7835 (5) Å	θ = 3.0–27.5°
b = 14.6460 (4) Å	µ = 0.09 mm⁻¹
c = 8.8713 (2) Å	T = 153 K
β = 99.551 (1)°	Block, yellow
V = 1766.05 (9) Å³	0.36 × 0.25 × 0.14 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2029 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→18
T_min = 0.864, T_max = 0.988	l = −10→11
8563 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0522P)² + 0.3553P] where P = (F_o² + 2F_c²)/3
2029 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.19 e Å⁻³
4 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₁₉NO₃	V = 1766.05 (9) Å³
M_r = 345.38	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 13.7835 (5) Å	µ = 0.09 mm⁻¹
b = 14.6460 (4) Å	T = 153 K
c = 8.8713 (2) Å	0.36 × 0.25 × 0.14 mm
β = 99.551 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2029 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1958 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.988	R_int = 0.016
8563 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	4 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.19 e Å⁻³
2029 reflections	Δρ_min = −0.27 e Å⁻³
244 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.50000 (10)	0.89966 (8)	0.50000 (13)	0.0251 (3)
O2	0.57192 (9)	0.73346 (8)	0.07916 (12)	0.0221 (3)
O3	0.57203 (10)	0.88667 (8)	0.05998 (13)	0.0243 (3)
N1	0.54563 (13)	0.98073 (10)	0.31277 (17)	0.0289 (3)
H11	0.5480 (18)	1.0271 (12)	0.376 (2)	0.038 (7)*
H12	0.5641 (18)	0.9858 (18)	0.2234 (17)	0.040 (7)*
C1	0.53026 (11)	0.72524 (11)	0.36834 (17)	0.0176 (3)
H1	0.4968	0.6810	0.2908	0.021*
C2	0.63064 (12)	0.68559 (10)	0.43558 (18)	0.0199 (3)
C3	0.66322 (13)	0.60409 (11)	0.3813 (2)	0.0254 (4)
H3	0.6228	0.5728	0.3004	0.031*
C4	0.75447 (14)	0.56763 (13)	0.4441 (3)	0.0335 (4)
H4	0.7759	0.5118	0.4060	0.040*
C5	0.81378 (14)	0.61264 (14)	0.5619 (3)	0.0364 (5)
H5	0.8756	0.5874	0.6056	0.044*
C6	0.78287 (14)	0.69460 (15)	0.6159 (2)	0.0357 (5)
H6	0.8239	0.7260	0.6959	0.043*
C7	0.69180 (13)	0.73093 (13)	0.5532 (2)	0.0276 (4)
H7	0.6711	0.7871	0.5908	0.033*
C8	0.46549 (12)	0.73777 (11)	0.48933 (17)	0.0191 (3)
C9	0.41664 (12)	0.66266 (12)	0.54835 (17)	0.0204 (3)
C10	0.43046 (13)	0.57101 (12)	0.50594 (18)	0.0247 (3)
H10	0.4732	0.5580	0.4349	0.030*
C11	0.38294 (15)	0.50035 (13)	0.5660 (2)	0.0305 (4)
H11A	0.3941	0.4392	0.5378	0.037*
C12	0.31800 (14)	0.51858 (14)	0.6691 (2)	0.0322 (4)
H12A	0.2840	0.4698	0.7079	0.039*
C13	0.30372 (14)	0.60584 (14)	0.7134 (2)	0.0297 (4)
H13	0.2601	0.6172	0.7837	0.036*
C14	0.35287 (12)	0.68005 (13)	0.65636 (19)	0.0240 (4)
C15	0.34044 (13)	0.77096 (13)	0.7054 (2)	0.0278 (4)
H15	0.2974	0.7827	0.7764	0.033*
C16	0.38932 (14)	0.84127 (13)	0.65223 (19)	0.0262 (4)
H16	0.3816	0.9018	0.6867	0.031*
C17	0.45205 (12)	0.82298 (12)	0.54462 (18)	0.0217 (3)
C18	0.53012 (12)	0.89655 (11)	0.36102 (17)	0.0213 (3)
C19	0.53928 (12)	0.81562 (10)	0.28807 (18)	0.0186 (3)
C20	0.56246 (12)	0.81763 (10)	0.13523 (18)	0.0185 (3)
C21	0.59893 (13)	0.72831 (11)	−0.07209 (18)	0.0239 (3)
H21A	0.6644	0.7561	−0.0717	0.029*
H21B	0.5502	0.7611	−0.1475	0.029*
C22	0.60081 (17)	0.62865 (13)	−0.1116 (2)	0.0336 (4)
H22A	0.5345	0.6031	−0.1183	0.050*
H22B	0.6459	0.5964	−0.0321	0.050*
H22C	0.6232	0.6214	−0.2101	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0364 (7)	0.0209 (6)	0.0193 (5)	−0.0010 (5)	0.0086 (5)	−0.0031 (4)
O2	0.0328 (6)	0.0182 (5)	0.0168 (5)	0.0025 (5)	0.0084 (4)	0.0014 (4)
O3	0.0334 (7)	0.0200 (6)	0.0199 (5)	0.0007 (5)	0.0059 (5)	0.0027 (4)
N1	0.0473 (9)	0.0188 (7)	0.0216 (7)	−0.0023 (6)	0.0088 (6)	−0.0033 (6)
C1	0.0189 (7)	0.0185 (7)	0.0156 (6)	0.0004 (5)	0.0036 (5)	0.0004 (5)
C2	0.0194 (7)	0.0223 (7)	0.0190 (7)	−0.0004 (6)	0.0061 (5)	0.0069 (6)
C3	0.0223 (8)	0.0188 (7)	0.0357 (10)	−0.0010 (6)	0.0060 (7)	0.0053 (6)
C4	0.0243 (8)	0.0223 (8)	0.0553 (12)	0.0029 (7)	0.0108 (8)	0.0109 (8)
C5	0.0202 (8)	0.0387 (11)	0.0489 (12)	0.0022 (7)	0.0012 (8)	0.0183 (9)
C6	0.0245 (9)	0.0507 (12)	0.0298 (9)	−0.0019 (8)	−0.0014 (7)	0.0060 (8)
C7	0.0236 (8)	0.0359 (9)	0.0230 (8)	−0.0006 (7)	0.0026 (6)	0.0006 (7)
C8	0.0187 (7)	0.0215 (7)	0.0168 (7)	0.0006 (6)	0.0024 (6)	0.0015 (6)
C9	0.0187 (7)	0.0267 (8)	0.0155 (6)	−0.0001 (6)	0.0017 (5)	0.0015 (6)
C10	0.0279 (8)	0.0250 (8)	0.0221 (8)	−0.0044 (6)	0.0067 (6)	0.0003 (6)
C11	0.0365 (10)	0.0277 (8)	0.0272 (9)	−0.0071 (8)	0.0053 (7)	0.0014 (7)
C12	0.0309 (9)	0.0365 (10)	0.0296 (9)	−0.0103 (7)	0.0059 (7)	0.0065 (8)
C13	0.0225 (8)	0.0440 (10)	0.0239 (8)	−0.0020 (7)	0.0078 (6)	0.0057 (7)
C14	0.0190 (7)	0.0320 (9)	0.0208 (8)	0.0011 (6)	0.0030 (6)	0.0024 (6)
C15	0.0241 (8)	0.0376 (10)	0.0233 (8)	0.0063 (7)	0.0085 (6)	−0.0007 (7)
C16	0.0277 (8)	0.0276 (9)	0.0240 (8)	0.0056 (7)	0.0063 (7)	−0.0033 (7)
C17	0.0228 (8)	0.0251 (8)	0.0173 (7)	0.0017 (6)	0.0031 (6)	0.0007 (6)
C18	0.0254 (8)	0.0226 (8)	0.0153 (7)	0.0002 (6)	0.0020 (6)	0.0005 (6)
C19	0.0206 (7)	0.0177 (7)	0.0169 (7)	0.0001 (5)	0.0016 (6)	0.0018 (5)
C20	0.0199 (7)	0.0173 (7)	0.0180 (7)	0.0018 (5)	0.0021 (5)	0.0012 (5)
C21	0.0330 (9)	0.0233 (8)	0.0173 (8)	0.0011 (7)	0.0092 (6)	−0.0003 (6)
C22	0.0519 (11)	0.0238 (8)	0.0280 (9)	0.0062 (8)	0.0155 (8)	−0.0017 (7)

Geometric parameters (Å, º) top

O1—C18	1.3654 (19)	C8—C9	1.433 (2)
O1—C17	1.393 (2)	C9—C10	1.415 (2)
O2—C20	1.3437 (19)	C9—C14	1.427 (2)
O2—C21	1.4527 (18)	C10—C11	1.378 (2)
O3—C20	1.231 (2)	C10—H10	0.9500
N1—C18	1.334 (2)	C11—C12	1.407 (3)
N1—H11	0.876 (10)	C11—H11A	0.9500
N1—H12	0.875 (10)	C12—C13	1.361 (3)
C1—C8	1.517 (2)	C12—H12A	0.9500
C1—C19	1.518 (2)	C13—C14	1.418 (3)
C1—C2	1.528 (2)	C13—H13	0.9500
C1—H1	1.0000	C14—C15	1.420 (3)
C2—C3	1.389 (2)	C15—C16	1.357 (3)
C2—C7	1.396 (2)	C15—H15	0.9500
C3—C4	1.395 (2)	C16—C17	1.416 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.382 (3)	C18—C19	1.366 (2)
C4—H4	0.9500	C19—C20	1.444 (2)
C5—C6	1.386 (3)	C21—C22	1.502 (2)
C5—H5	0.9500	C21—H21A	0.9900
C6—C7	1.392 (3)	C21—H21B	0.9900
C6—H6	0.9500	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C17	1.365 (2)	C22—H22C	0.9800

C18—O1—C17	117.34 (13)	C12—C11—H11A	119.9
C20—O2—C21	116.42 (12)	C13—C12—C11	120.25 (17)
C18—N1—H11	120.2 (17)	C13—C12—H12A	119.9
C18—N1—H12	117.1 (17)	C11—C12—H12A	119.9
H11—N1—H12	122 (2)	C12—C13—C14	121.08 (17)
C8—C1—C19	109.27 (13)	C12—C13—H13	119.5
C8—C1—C2	111.78 (13)	C14—C13—H13	119.5
C19—C1—C2	112.04 (12)	C13—C14—C15	121.35 (16)
C8—C1—H1	107.9	C13—C14—C9	119.15 (16)
C19—C1—H1	107.9	C15—C14—C9	119.50 (15)
C2—C1—H1	107.9	C16—C15—C14	120.85 (16)
C3—C2—C7	118.56 (15)	C16—C15—H15	119.6
C3—C2—C1	121.00 (14)	C14—C15—H15	119.6
C7—C2—C1	120.44 (15)	C15—C16—C17	118.99 (16)
C2—C3—C4	120.82 (17)	C15—C16—H16	120.5
C2—C3—H3	119.6	C17—C16—H16	120.5
C4—C3—H3	119.6	C8—C17—O1	122.40 (14)
C5—C4—C3	120.03 (18)	C8—C17—C16	123.36 (16)
C5—C4—H4	120.0	O1—C17—C16	114.24 (14)
C3—C4—H4	120.0	N1—C18—O1	110.36 (14)
C4—C5—C6	119.83 (17)	N1—C18—C19	128.13 (15)
C4—C5—H5	120.1	O1—C18—C19	121.50 (14)
C6—C5—H5	120.1	C18—C19—C20	118.64 (14)
C5—C6—C7	120.10 (18)	C18—C19—C1	120.87 (14)
C5—C6—H6	120.0	C20—C19—C1	120.42 (13)
C7—C6—H6	120.0	O3—C20—O2	121.82 (15)
C6—C7—C2	120.65 (18)	O3—C20—C19	125.89 (14)
C6—C7—H7	119.7	O2—C20—C19	112.28 (13)
C2—C7—H7	119.7	O2—C21—C22	106.43 (13)
C17—C8—C9	118.06 (14)	O2—C21—H21A	110.4
C17—C8—C1	119.73 (14)	C22—C21—H21A	110.4
C9—C8—C1	122.20 (14)	O2—C21—H21B	110.4
C10—C9—C14	118.23 (15)	C22—C21—H21B	110.4
C10—C9—C8	122.59 (15)	H21A—C21—H21B	108.6
C14—C9—C8	119.17 (15)	C21—C22—H22A	109.5
C11—C10—C9	121.04 (16)	C21—C22—H22B	109.5
C11—C10—H10	119.5	H22A—C22—H22B	109.5
C9—C10—H10	119.5	C21—C22—H22C	109.5
C10—C11—C12	120.21 (18)	H22A—C22—H22C	109.5
C10—C11—H11A	119.9	H22B—C22—H22C	109.5

C8—C1—C2—C3	121.86 (16)	C8—C9—C14—C15	−1.2 (2)
C19—C1—C2—C3	−115.10 (16)	C13—C14—C15—C16	178.73 (17)
C8—C1—C2—C7	−58.27 (19)	C9—C14—C15—C16	−0.8 (3)
C19—C1—C2—C7	64.76 (19)	C14—C15—C16—C17	1.0 (3)
C7—C2—C3—C4	0.8 (2)	C9—C8—C17—O1	176.85 (14)
C1—C2—C3—C4	−179.31 (16)	C1—C8—C17—O1	−3.5 (2)
C2—C3—C4—C5	0.0 (3)	C9—C8—C17—C16	−2.7 (2)
C3—C4—C5—C6	−0.8 (3)	C1—C8—C17—C16	176.99 (16)
C4—C5—C6—C7	0.8 (3)	C18—O1—C17—C8	24.8 (2)
C5—C6—C7—C2	0.0 (3)	C18—O1—C17—C16	−155.62 (15)
C3—C2—C7—C6	−0.8 (3)	C15—C16—C17—C8	0.8 (3)
C1—C2—C7—C6	179.31 (16)	C15—C16—C17—O1	−178.81 (15)
C19—C1—C8—C17	−20.86 (19)	C17—O1—C18—N1	160.53 (15)
C2—C1—C8—C17	103.73 (16)	C17—O1—C18—C19	−18.3 (2)
C19—C1—C8—C9	158.81 (13)	N1—C18—C19—C20	−4.4 (3)
C2—C1—C8—C9	−76.60 (18)	O1—C18—C19—C20	174.24 (15)
C17—C8—C9—C10	−175.95 (15)	N1—C18—C19—C1	172.70 (16)
C1—C8—C9—C10	4.4 (2)	O1—C18—C19—C1	−8.7 (2)
C17—C8—C9—C14	2.8 (2)	C8—C1—C19—C18	27.1 (2)
C1—C8—C9—C14	−176.84 (15)	C2—C1—C19—C18	−97.31 (17)
C14—C9—C10—C11	0.6 (2)	C8—C1—C19—C20	−155.85 (14)
C8—C9—C10—C11	179.41 (15)	C2—C1—C19—C20	79.71 (17)
C9—C10—C11—C12	1.2 (3)	C21—O2—C20—O3	3.0 (2)
C10—C11—C12—C13	−1.8 (3)	C21—O2—C20—C19	−177.75 (13)
C11—C12—C13—C14	0.5 (3)	C18—C19—C20—O3	−2.5 (2)
C12—C13—C14—C15	−178.19 (18)	C1—C19—C20—O3	−179.59 (16)
C12—C13—C14—C9	1.3 (3)	C18—C19—C20—O2	178.28 (15)
C10—C9—C14—C13	−1.9 (2)	C1—C19—C20—O2	1.20 (19)
C8—C9—C14—C13	179.31 (15)	C20—O2—C21—C22	−177.74 (14)
C10—C9—C14—C15	177.66 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O3ⁱ	0.88 (1)	2.05 (1)	2.907 (2)	166 (2)
N1—H12···O3	0.88 (1)	2.07 (2)	2.707 (2)	129 (2)

Symmetry code: (i) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉NO₃
M_r	345.38
Crystal system, space group	Monoclinic, Cc
Temperature (K)	153
a, b, c (Å)	13.7835 (5), 14.6460 (4), 8.8713 (2)
β (°)	99.551 (1)
V (Å³)	1766.05 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.25 × 0.14

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.864, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	8563, 2029, 1958
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.078, 1.09
No. of reflections	2029
No. of parameters	244
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.27

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O3ⁱ	0.88 (1)	2.05 (1)	2.907 (2)	166 (2)
N1—H12···O3	0.88 (1)	2.07 (2)	2.707 (2)	129 (2)

Symmetry code: (i) x, −y+2, z+1/2.

Acknowledgements

We thank the Huangshi Institute of Technology (grant No. 08yjz23B) and the University of Malaya for supporting this work.

References

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