Crystal structure of ethyl (4R)-2-amino-7-hy­droxy-4-phenyl-4H-chromene-3-carboxyl­ate

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Younes, S.H.H.; Albayati, M.R.

doi:10.1107/S2056989015012013

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o519-o520

doi:10.1107/S2056989015012013

Open

access

Crystal structure of ethyl (4R)-2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Sabry H. H. Younes ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bFaculty of Science & Engineering, School of Healthcare Science, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. McArdle, National University of Ireland, Ireland (Received 21 June 2015; accepted 23 June 2015; online 27 June 2015)

In the title compound, C₁₈H₁₇NO₄, the dihedral angle between the phenyl ring and the fused six-membered ring is 77.65 (4)°. The conformation of the molecule is determined in part by an intramolecular N—H⋯O hydrogen bond between the amino H atom and the carbonyl O atom, forming an S(6) motif. In the crystal, molecules are linked into N—H⋯O hydrogen-bonded inversion dimers which are then connected into chains along [001], forming a two-dimensional network parallel to (100) via O—H⋯O hydrogen bonds. C—H⋯O interactions further contribute to the crystal stability. The ethyl group is disordered over two sets of sites in a 0.801 (5):0.199 (5) ratio.

Keywords: crystal structure; amino chromenes; 4H-chromene; hydrogen bonding.

CCDC reference: 1408238

1. Related literature

For background to the synthesis and biological activity of molecules having a 4H-chromene or 4H-benzochromene residue, see: Kiyani & Ghorbani (2014 ); Kale et al. (2013 ); Sabry et al. (2011 ); Kidwai et al. (2010 ); Mungra et al. (2011 ); Cingolani et al. (1969 ); Wu et al. (2003 ); Perrella et al. (1994 ); Patil et al. (1993 ); Emmadi et al. (2012 ); Wang et al. (2003 ); Armesto et al. (1989 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₇NO₄
M_r = 311.32
Monoclinic, C 2/c
a = 31.5071 (7) Å
b = 5.8582 (1) Å
c = 21.2249 (5) Å
β = 130.180 (1)°
V = 2993.11 (11) Å³
Z = 8
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 150 K
0.22 × 0.18 × 0.02 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.91, T_max = 0.98
11241 measured reflections
2891 independent reflections
2348 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.05
2891 reflections
227 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2ⁱ	0.99	2.58	3.312 (3)	131
C6—H6⋯O1ⁱⁱ	0.95	2.56	3.4736 (17)	163
N1—H1B⋯O3	0.88 (2)	1.998 (19)	2.6840 (18)	133.7 (16)
N1—H1A⋯O2ⁱⁱ	0.93 (2)	2.15 (2)	3.0710 (18)	169.6 (17)
O2—H2A⋯O3ⁱⁱⁱ	0.90 (2)	1.83 (2)	2.7331 (15)	179 (2)
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1408238

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015012013/qm2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015012013/qm2111Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015012013/qm2111Isup3.cml

checkCIF report

Comment top

Besides the various biological properties of 2-Amino-4H-Chromenes, they also act as important synthetic building blocks for various bio-active molecules (Kiyani & Ghorbani, 2014; Kale et al., 2013; Sabry et al., 2011; Kidwai et al., 2010). During the last decade, such compounds had shown interesting pharmacological properties such as antimicrobial and anti-tuberculosis agents (Mungra et al., 2011), anticoagulant (Cingolani et al., 1969), anticancer (Wu et al., 2003), antitumour (Perrella, et al., 1994), cytotoxic and anti-HIV activities (Patil et al., 1993; Emmadi, et al., 2012). Also, chromenes are also structural features of various natural products (Wang et al., 2003) and possess useful photochemical properties (Armesto et al., 1989).

In the title molecule, the dihedral angle between the phenyl ring (C13–C18) and the C2–C7 ring is 77.65 (4)°. A puckering analysis of the heterocyclic ring gave Q = 0.118 (2) Å, θ = 95.1 (8)° and ϕ = 352.0 (8)°. The conformation of the molecule is determined in part by an intramolecular N1—H1B···O3 hydrogen bond. Pairwise N1—H1A···O2ⁱ (i: 1 - x, -y, 1 - z) hydrogen bonds form dimers which are then connected into chains via O2—H2A···O3ⁱⁱ (ii: x, 1 - y, -1/2 + z) hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For background to the synthesis and biological activity of molecules having a 4H-chromene or 4H-benzochromene residue, see: Kiyani & Ghorbani (2014); Kale et al. (2013); Sabry et al. (2011); Kidwai et al. (2010); Mungra et al. (2011); Cingolani et al. (1969); Wu et al. (2003); Perrella et al. (1994); Patil et al. (1993); Emmadi et al. (2012); Wang et al. (2003); Armesto et al. (1989).

Experimental top

The title compound was synthesized by the reaction of (E)-ethyl 3-(phenyl)-2-cyanoacrylate (1 mmol, 201 mg) and 1,3-Benzenediol (1 mmol, 110 mg) catalyzed by Et₃N in 10 ml e thanol at the refuxing temperature. After cooling, the solvent was removed under reduced pressure and the residue was washed with cold ethanol and recrystallized from ethanol to afford pure colourless crystals suitable for X-ray diffraction in 92% yeild and M.p 491 K.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with labeling scheme and 50% probability ellipsoids. Only one orientation of the disordered ethyl group is shown.
	Fig. 2. Packing viewed down the b axis. N—H···O and O—H···O hydrogen bonds are shown, respectively as blue and red dotted lines.

Ethyl (4R)-2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate top

Crystal data top

C₁₈H₁₇NO₄	F(000) = 1312
M_r = 311.32	D_x = 1.382 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 31.5071 (7) Å	Cell parameters from 6704 reflections
b = 5.8582 (1) Å	θ = 3.7–72.2°
c = 21.2249 (5) Å	µ = 0.81 mm⁻¹
β = 130.180 (1)°	T = 150 K
V = 2993.11 (11) Å³	Plate, colourless
Z = 8	0.22 × 0.18 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2891 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2348 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
ω scans	θ_max = 72.2°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −38→36
T_min = 0.91, T_max = 0.98	k = −6→7
11241 measured reflections	l = −24→26

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)] = 0.038	Hydrogen site location: mixed
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.049P)² + 1.7699P] where P = (F_o² + 2F_c²)/3
2891 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.27 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₁₇NO₄	V = 2993.11 (11) Å³
M_r = 311.32	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 31.5071 (7) Å	µ = 0.81 mm⁻¹
b = 5.8582 (1) Å	T = 150 K
c = 21.2249 (5) Å	0.22 × 0.18 × 0.02 mm
β = 130.180 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2891 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2348 reflections with I > 2σ(I)
T_min = 0.91, T_max = 0.98	R_int = 0.033
11241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
2891 reflections	Δρ_min = −0.25 e Å⁻³
227 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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. The ethyl group (C11,C12) is disordered over two sites. The components of the disorder were refined subject to restraints that their geometries be approximately the same.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.45362 (4)	0.22755 (17)	0.51953 (6)	0.0270 (2)
O2	0.46127 (4)	0.21959 (19)	0.30568 (6)	0.0302 (3)
H2A	0.4494 (9)	0.294 (4)	0.2598 (14)	0.056 (6)*
O3	0.42602 (4)	0.5543 (2)	0.66661 (6)	0.0340 (3)
O4	0.37668 (5)	0.82032 (19)	0.56697 (6)	0.0338 (3)
N1	0.46907 (5)	0.2182 (3)	0.63712 (8)	0.0305 (3)
H1A	0.4890 (8)	0.084 (4)	0.6479 (12)	0.049 (5)*
H1B	0.4647 (8)	0.277 (3)	0.6709 (12)	0.039 (5)*
C1	0.38998 (6)	0.6527 (2)	0.46364 (8)	0.0242 (3)
H1	0.4037	0.8139	0.4768	0.029*
C2	0.40953 (5)	0.5419 (2)	0.42173 (8)	0.0228 (3)
C3	0.39849 (6)	0.6388 (3)	0.35231 (8)	0.0256 (3)
H3	0.3789	0.7795	0.3318	0.031*
C4	0.41512 (6)	0.5365 (3)	0.31246 (8)	0.0260 (3)
H4	0.4070	0.6063	0.2654	0.031*
C5	0.44383 (6)	0.3298 (2)	0.34225 (8)	0.0241 (3)
C6	0.45583 (6)	0.2297 (2)	0.41125 (8)	0.0243 (3)
H6	0.4754	0.0892	0.4320	0.029*
C7	0.43866 (5)	0.3386 (2)	0.44957 (8)	0.0227 (3)
C8	0.44500 (6)	0.3350 (3)	0.56735 (8)	0.0244 (3)
C9	0.41527 (5)	0.5333 (3)	0.54438 (8)	0.0248 (3)
C10	0.40769 (6)	0.6307 (3)	0.59859 (9)	0.0274 (3)
C11	0.35861 (16)	0.9101 (9)	0.60985 (17)	0.0450 (8)	0.801 (5)
H11A	0.3904	0.9738	0.6641	0.054*	0.801 (5)
H11B	0.3409	0.7892	0.6185	0.054*	0.801 (5)
C12	0.31703 (14)	1.0965 (6)	0.55374 (19)	0.0619 (10)	0.801 (5)
H12A	0.3029	1.1656	0.5791	0.093*	0.801 (5)
H12B	0.3353	1.2137	0.5456	0.093*	0.801 (5)
H12C	0.2861	1.0303	0.5003	0.093*	0.801 (5)
C11A	0.3518 (6)	0.940 (5)	0.5958 (8)	0.0450 (8)	0.199 (5)
H11C	0.3677	1.0951	0.6149	0.054*	0.199 (5)
H11D	0.3586	0.8561	0.6421	0.054*	0.199 (5)
C12A	0.2899 (5)	0.953 (3)	0.5230 (7)	0.0619 (10)	0.199 (5)
H12D	0.2712	1.0330	0.5397	0.093*	0.199 (5)
H12E	0.2838	1.0361	0.4777	0.093*	0.199 (5)
H12F	0.2748	0.7983	0.5047	0.093*	0.199 (5)
C13	0.32653 (6)	0.6603 (2)	0.40441 (8)	0.0248 (3)
C14	0.29555 (6)	0.4724 (3)	0.39345 (9)	0.0289 (3)
H14	0.3139	0.3368	0.4240	0.035*
C15	0.23796 (6)	0.4812 (3)	0.33820 (10)	0.0369 (4)
H15	0.2171	0.3520	0.3314	0.044*
C16	0.21071 (7)	0.6774 (3)	0.29294 (10)	0.0415 (4)
H16	0.1713	0.6836	0.2555	0.050*
C17	0.24104 (7)	0.8635 (3)	0.30240 (10)	0.0399 (4)
H17	0.2225	0.9975	0.2707	0.048*
C18	0.29867 (7)	0.8557 (3)	0.35817 (9)	0.0328 (3)
H18	0.3193	0.9854	0.3648	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0334 (5)	0.0318 (5)	0.0209 (5)	0.0037 (4)	0.0198 (4)	0.0024 (4)
O2	0.0346 (6)	0.0392 (6)	0.0237 (5)	0.0060 (5)	0.0220 (5)	0.0032 (5)
O3	0.0372 (6)	0.0470 (7)	0.0225 (5)	0.0043 (5)	0.0214 (5)	0.0005 (5)
O4	0.0401 (6)	0.0395 (6)	0.0287 (5)	0.0059 (5)	0.0254 (5)	−0.0007 (5)
N1	0.0331 (7)	0.0414 (8)	0.0214 (6)	0.0060 (6)	0.0196 (6)	0.0041 (6)
C1	0.0266 (7)	0.0270 (7)	0.0210 (7)	−0.0031 (6)	0.0163 (6)	−0.0034 (6)
C2	0.0209 (6)	0.0280 (7)	0.0191 (6)	−0.0036 (6)	0.0127 (5)	−0.0033 (6)
C3	0.0240 (7)	0.0293 (7)	0.0235 (7)	−0.0011 (6)	0.0153 (6)	0.0008 (6)
C4	0.0264 (7)	0.0328 (8)	0.0208 (7)	−0.0026 (6)	0.0161 (6)	0.0015 (6)
C5	0.0216 (6)	0.0334 (8)	0.0192 (6)	−0.0036 (6)	0.0140 (5)	−0.0044 (6)
C6	0.0227 (7)	0.0287 (7)	0.0202 (7)	0.0003 (6)	0.0134 (6)	0.0001 (6)
C7	0.0221 (6)	0.0297 (7)	0.0156 (6)	−0.0045 (5)	0.0118 (5)	−0.0011 (5)
C8	0.0221 (7)	0.0349 (8)	0.0174 (6)	−0.0044 (6)	0.0132 (6)	−0.0036 (6)
C9	0.0220 (7)	0.0334 (8)	0.0182 (6)	−0.0026 (6)	0.0127 (6)	−0.0031 (6)
C10	0.0241 (7)	0.0358 (8)	0.0225 (7)	−0.0031 (6)	0.0151 (6)	−0.0042 (6)
C11	0.0614 (14)	0.050 (2)	0.0456 (14)	0.0246 (12)	0.0448 (12)	0.0156 (16)
C12	0.079 (2)	0.074 (2)	0.0624 (18)	0.0394 (17)	0.0588 (18)	0.0292 (16)
C11A	0.0614 (14)	0.050 (2)	0.0456 (14)	0.0246 (12)	0.0448 (12)	0.0156 (16)
C12A	0.079 (2)	0.074 (2)	0.0624 (18)	0.0394 (17)	0.0588 (18)	0.0292 (16)
C13	0.0276 (7)	0.0305 (7)	0.0194 (6)	0.0023 (6)	0.0166 (6)	−0.0012 (6)
C14	0.0298 (7)	0.0344 (8)	0.0252 (7)	0.0014 (6)	0.0190 (6)	−0.0008 (6)
C15	0.0302 (8)	0.0528 (10)	0.0314 (8)	−0.0043 (7)	0.0216 (7)	−0.0079 (8)
C16	0.0257 (8)	0.0665 (12)	0.0272 (8)	0.0113 (8)	0.0148 (7)	−0.0040 (8)
C17	0.0418 (9)	0.0470 (10)	0.0285 (8)	0.0186 (8)	0.0216 (7)	0.0054 (7)
C18	0.0407 (9)	0.0333 (8)	0.0283 (8)	0.0068 (7)	0.0241 (7)	0.0021 (7)

Geometric parameters (Å, º) top

O1—C8	1.3622 (16)	C9—C10	1.4358 (19)
O1—C7	1.3954 (16)	C11—C12	1.521 (4)
O2—C5	1.3679 (17)	C11—H11A	0.9900
O2—H2A	0.90 (2)	C11—H11B	0.9900
O3—C10	1.2419 (18)	C12—H12A	0.9800
O4—C10	1.3387 (18)	C12—H12B	0.9800
O4—C11	1.448 (2)	C12—H12C	0.9800
O4—C11A	1.448 (4)	C11A—C12A	1.519 (6)
N1—C8	1.3366 (19)	C11A—H11C	0.9900
N1—H1A	0.93 (2)	C11A—H11D	0.9900
N1—H1B	0.88 (2)	C12A—H12D	0.9800
C1—C2	1.5164 (18)	C12A—H12E	0.9800
C1—C9	1.5165 (19)	C12A—H12F	0.9800
C1—C13	1.5284 (19)	C13—C14	1.388 (2)
C1—H1	1.0000	C13—C18	1.390 (2)
C2—C7	1.382 (2)	C14—C15	1.387 (2)
C2—C3	1.3976 (19)	C14—H14	0.9500
C3—C4	1.386 (2)	C15—C16	1.384 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.395 (2)	C16—C17	1.376 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.3846 (19)	C17—C18	1.388 (2)
C6—C7	1.3886 (19)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C8—C9	1.369 (2)

C8—O1—C7	118.99 (11)	O4—C11—H11A	110.8
C5—O2—H2A	110.5 (14)	C12—C11—H11A	110.8
C10—O4—C11	116.23 (19)	O4—C11—H11B	110.8
C10—O4—C11A	127.5 (10)	C12—C11—H11B	110.8
C8—N1—H1A	120.8 (12)	H11A—C11—H11B	108.8
C8—N1—H1B	115.2 (12)	C11—C12—H12A	109.5
H1A—N1—H1B	124.0 (17)	C11—C12—H12B	109.5
C2—C1—C9	110.43 (12)	H12A—C12—H12B	109.5
C2—C1—C13	109.92 (11)	C11—C12—H12C	109.5
C9—C1—C13	113.43 (11)	H12A—C12—H12C	109.5
C2—C1—H1	107.6	H12B—C12—H12C	109.5
C9—C1—H1	107.6	O4—C11A—C12A	106.5 (7)
C13—C1—H1	107.6	O4—C11A—H11C	110.4
C7—C2—C3	116.48 (12)	C12A—C11A—H11C	110.4
C7—C2—C1	121.82 (12)	O4—C11A—H11D	110.4
C3—C2—C1	121.69 (13)	C12A—C11A—H11D	110.4
C4—C3—C2	122.18 (14)	H11C—C11A—H11D	108.6
C4—C3—H3	118.9	C11A—C12A—H12D	109.5
C2—C3—H3	118.9	C11A—C12A—H12E	109.5
C3—C4—C5	119.26 (13)	H12D—C12A—H12E	109.5
C3—C4—H4	120.4	C11A—C12A—H12F	109.5
C5—C4—H4	120.4	H12D—C12A—H12F	109.5
O2—C5—C6	117.71 (13)	H12E—C12A—H12F	109.5
O2—C5—C4	122.20 (12)	C14—C13—C18	118.64 (14)
C6—C5—C4	120.09 (13)	C14—C13—C1	121.35 (13)
C5—C6—C7	118.79 (13)	C18—C13—C1	119.98 (14)
C5—C6—H6	120.6	C15—C14—C13	120.48 (15)
C7—C6—H6	120.6	C15—C14—H14	119.8
C2—C7—C6	123.19 (12)	C13—C14—H14	119.8
C2—C7—O1	122.14 (12)	C16—C15—C14	120.31 (16)
C6—C7—O1	114.67 (12)	C16—C15—H15	119.8
N1—C8—O1	110.23 (13)	C14—C15—H15	119.8
N1—C8—C9	126.67 (13)	C17—C16—C15	119.66 (15)
O1—C8—C9	123.09 (12)	C17—C16—H16	120.2
C8—C9—C10	118.78 (13)	C15—C16—H16	120.2
C8—C9—C1	122.26 (12)	C16—C17—C18	120.10 (16)
C10—C9—C1	118.96 (13)	C16—C17—H17	119.9
O3—C10—O4	121.56 (13)	C18—C17—H17	119.9
O3—C10—C9	126.52 (14)	C17—C18—C13	120.79 (16)
O4—C10—C9	111.92 (12)	C17—C18—H18	119.6
O4—C11—C12	105.0 (2)	C13—C18—H18	119.6

C9—C1—C2—C7	9.72 (18)	C13—C1—C9—C8	115.70 (15)
C13—C1—C2—C7	−116.18 (14)	C2—C1—C9—C10	171.99 (12)
C9—C1—C2—C3	−170.99 (12)	C13—C1—C9—C10	−64.11 (17)
C13—C1—C2—C3	63.11 (17)	C11—O4—C10—O3	−9.3 (3)
C7—C2—C3—C4	0.7 (2)	C11A—O4—C10—O3	−11.6 (12)
C1—C2—C3—C4	−178.58 (13)	C11—O4—C10—C9	169.8 (3)
C2—C3—C4—C5	0.0 (2)	C11A—O4—C10—C9	167.5 (12)
C3—C4—C5—O2	179.81 (13)	C8—C9—C10—O3	0.7 (2)
C3—C4—C5—C6	−0.5 (2)	C1—C9—C10—O3	−179.51 (14)
O2—C5—C6—C7	179.87 (12)	C8—C9—C10—O4	−178.39 (12)
C4—C5—C6—C7	0.1 (2)	C1—C9—C10—O4	1.43 (18)
C3—C2—C7—C6	−1.1 (2)	C10—O4—C11—C12	−170.7 (3)
C1—C2—C7—C6	178.23 (13)	C10—O4—C11A—C12A	−123.6 (13)
C3—C2—C7—O1	178.25 (12)	C2—C1—C13—C14	82.33 (16)
C1—C2—C7—O1	−2.4 (2)	C9—C1—C13—C14	−41.85 (18)
C5—C6—C7—C2	0.7 (2)	C2—C1—C13—C18	−95.55 (15)
C5—C6—C7—O1	−178.71 (12)	C9—C1—C13—C18	140.28 (13)
C8—O1—C7—C2	−7.73 (19)	C18—C13—C14—C15	−0.8 (2)
C8—O1—C7—C6	171.67 (11)	C1—C13—C14—C15	−178.73 (13)
C7—O1—C8—N1	−170.97 (11)	C13—C14—C15—C16	0.4 (2)
C7—O1—C8—C9	9.47 (19)	C14—C15—C16—C17	0.6 (2)
N1—C8—C9—C10	−0.6 (2)	C15—C16—C17—C18	−1.2 (2)
O1—C8—C9—C10	178.86 (12)	C16—C17—C18—C13	0.7 (2)
N1—C8—C9—C1	179.56 (13)	C14—C13—C18—C17	0.3 (2)
O1—C8—C9—C1	−1.0 (2)	C1—C13—C18—C17	178.21 (13)
C2—C1—C9—C8	−8.20 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.99	2.58	3.312 (3)	131
C6—H6···O1ⁱⁱ	0.95	2.56	3.4736 (17)	163
N1—H1B···O3	0.88 (2)	1.998 (19)	2.6840 (18)	133.7 (16)
N1—H1A···O2ⁱⁱ	0.93 (2)	2.15 (2)	3.0710 (18)	169.6 (17)
O2—H2A···O3ⁱⁱⁱ	0.90 (2)	1.83 (2)	2.7331 (15)	179 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.99	2.58	3.312 (3)	131
C6—H6···O1ⁱⁱ	0.95	2.56	3.4736 (17)	163
N1—H1B···O3	0.88 (2)	1.998 (19)	2.6840 (18)	133.7 (16)
N1—H1A···O2ⁱⁱ	0.93 (2)	2.15 (2)	3.0710 (18)	169.6 (17)
O2—H2A···O3ⁱⁱⁱ	0.90 (2)	1.83 (2)	2.7331 (15)	179 (2)

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

Acknowledgements

The support of NSF–MRI (grant No. 1228232) for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Armesto, D., Horspool, W. M., Martin, N., Ramos, A. & Seoane, C. (1989). J. Org. Chem. 54, 3069–3072. CrossRef CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT, SADABS, SHELXT and SHELXTL, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cingolani, G., Gualtieri, F. & Pigini, M. (1969). J. Med. Chem. 12, 531–532. CrossRef CAS PubMed Google Scholar
Emmadi, N. R., Atmakur, K., Chityal, G. K., Pombala, S. & Nanubolu, J. B. (2012). Bioorg. Med. Chem. Lett. 22, 7261–7264. CSD CrossRef CAS PubMed Google Scholar
Kale, S. R., Kahandal, S. S., Burange, A. S., Gawande, M. B. & Jayaram, R. V. (2013). Catal. Sci. Technol. 3, 2050–2056. CrossRef CAS Google Scholar
Kidwai, M., Poddar, R., Bhardwaj, S., Singh, S. & Luthra, M. P. (2010). Eur. J. Med. Chem. 45, 5031–5038. CrossRef CAS PubMed Google Scholar
Kiyani, H. & Ghorbani, F. (2014). J. Saudi Chem. Soc. 18, 689–701. CrossRef Google Scholar
Mungra, D. C., Patel, M. P., Rajani, D. P. & Patel, R. G. (2011). Eur. J. Med. Chem. 46, 4192–4200. Web of Science CrossRef CAS PubMed Google Scholar
Patil, A. D., Freyer, A. J., Eggleston, D. S., Haltiwanger, R. C., Bean, M. F., Taylor, P. B., Caranfa, M. J., Breen, A. L., Bartus, H. R., Johnson, R. K., et al. (1993). J. Med. Chem. 36, 4131–4138. CSD CrossRef CAS PubMed Google Scholar
Perrella, F. W., Chen, S. F., Behrens, D. L., Kaltenbach, R. F. & Seitz, S. P. (1994). J. Med. Chem. 37, 2232–2237. CrossRef CAS PubMed Google Scholar
Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765–772. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wang, X. S., Shi, D. Q., Tu, S. T. & Yao, C. S. (2003). Synth. Commun. 33, 119–126. CSD CrossRef CAS Google Scholar
Wu, J. Y. C., Fong, W. F., Zhang, J. X., Leung, C. H., Kwong, H. L., Yang, M. S., Li, D. & Cheung, H. (2003). Eur. J. Pharmacol. 473, 9–17. CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o519-o520

doi:10.1107/S2056989015012013

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of ethyl (4R)-2-amino-7-hy­dr­oxy-4-phenyl-4H-chromene-3-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl (4R)-2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate