(4R,7S)-2-Amino-4-(3,4-dimeth­oxy­phen­yl)-5-oxo-7-phenyl-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile monohydrate

Sun, R.; Wu, D.-D.; Wang, K.; Huang, W.; Ou, Y.-B.

doi:10.1107/S1600536811056285

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o409-o410

doi:10.1107/S1600536811056285

Open

access

(4R,7S)-2-Amino-4-(3,4-dimethoxyphenyl)-5-oxo-7-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile monohydrate

Rong Sun,^a,^b Dong-Dong Wu,^c Ke Wang,^d Wei Huang ^a and Yang-Bing Ou ^b ^*

^aShandong Academy of Chinese Medicine, Jinan 250014, People's Republic of China, ^bPostdoctoral Research Station of Shandong University of TCM, Jinan 250355, People's Republic of China, ^cShanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China, and ^dKey Laboratory of Nuclear Medicine, Ministry of Health, Jiangsu Key Laboratory of Molecular Nuclear Medicine, Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: sunrong107@163.com

(Received 16 December 2011; accepted 31 December 2011; online 14 January 2012)

The title compound, C₂₄H₂₂N₂O₄·H₂O, was obtained by the reaction of 3,4-dimethoxybenzaldehyde, malononitrile and 5-phenylcyclohexane-1,3-dione. The cyclohexyl and pyran rings show half-boat and V-shaped conformations, respectively. The dihedral angle between the phenyl and benzene ring planes is 30.67 (9)°. The organic molecules are packed in a two-dimensional network parallel to the bc plane stabilized by intermolecular N—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For background to 4-aryl-4H-chromene and its derivatives, see: Kemnitzer et al. (2004 , 2005 , 2007 , 2008 ); Gourdeau et al. (2004 ); Foroumadi et al. (2007 ); Mahdavi et al. (2011 ). For the synthesis of 4-aryl-4H-chromene and its derivatives, see: Wen et al. (2006 ); Kidwai et al. (2005 ); Yadav et al. (2009 ); Li et al. (2008 ). For related compounds, see: Gourdeau et al. (2004); Foroumadi et al. (2007).

Experimental

Crystal data

C₂₄H₂₂N₂O₄·H₂O
M_r = 420.45
Monoclinic, C 2/c
a = 29.008 (16) Å
b = 16.146 (8) Å
c = 12.068 (6) Å
β = 110.486 (9)°
V = 5295 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 291 K
0.38 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.972, T_max = 0.982
14295 measured reflections
5212 independent reflections
3266 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.132
S = 1.00
5212 reflections
305 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.86	2.20	3.042 (3)	167
N1—H1B⋯O2ⁱⁱ	0.86	2.12	2.935 (3)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811056285/bx2390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811056285/bx2390Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811056285/bx2390Isup3.cml

checkCIF report

Comment top

4-Aryl-4H-chromene compounds are a very important series of chromene derivatives, because they can be introduced as potent apoptosis inducing agents and exhibit anticancer activities (Kemnitzer et al., 2004, 2005, 2007, 2008; Gourdeau et al., 2004; Foroumadi et al., 2007; Mahdavi et al., 2011). Herein,we report the synthesis and crystal structure of a new 4-Aryl-4H-chromene derivative.The molecular structure of the title compound is shown in Fig.1. In structure of the title compound, the cyclohexyl ring shows in a half-boat conformation and the pyran ring shows in "V" shape. The dihedral angle between phenyl and benzene rings planes is 30.67 (9)°. The organic molecules are packing in a bi-dimensional network stabilized by intermolecular N—H···N, N—H···O hydrogen bonds, Table1.

Related literature top

For background to 4-aryl-4H-chromene and its derivatives, see: Kemnitzer et al. (2004, 2005, 2007, 2008); Gourdeau et al. (2004); Foroumadi et al. (2007); Mahdavi et al. (2011). For the synthesis of 4-aryl-4H-chromene and its derivatives, see: Wen et al. (2006); Kidwai et al. (2005); Yadav et al. (2009); Li et al. (2008). For related compounds, see: Gourdeau et al. (2004); Foroumadi et al. (2007).

Experimental top

The title compound was synthesized using methods described by Wen et al. 2006 & Kidwai et al. 2005. Single crystals of the title compound suitable for X-ray analysis were obtained by evaporating the solution of compound in ethanol at room temperature for one week.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement and the atom numbering scheme. The water molecule is omitted by clarity.

(4R,7S)-2-Amino-4-(3,4-dimethoxyphenyl)-5-oxo-7-phenyl- 5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile monohydrate top

Crystal data top

C₂₄H₂₂N₂O₄·H₂O	F(000) = 1776
M_r = 420.45	D_x = 1.055 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2449 reflections
a = 29.008 (16) Å	θ = 2.5–21.9°
b = 16.146 (8) Å	µ = 0.07 mm⁻¹
c = 12.068 (6) Å	T = 291 K
β = 110.486 (9)°	Block, colorless
V = 5295 (5) Å³	0.38 × 0.32 × 0.24 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	5212 independent reflections
Radiation source: sealed tube	3266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −35→28
T_min = 0.972, T_max = 0.982	k = −16→19
14295 measured reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0629P)²] where P = (F_o² + 2F_c²)/3
5212 reflections	(Δ/σ)_max < 0.001
305 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₄H₂₂N₂O₄·H₂O	V = 5295 (5) Å³
M_r = 420.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.008 (16) Å	µ = 0.07 mm⁻¹
b = 16.146 (8) Å	T = 291 K
c = 12.068 (6) Å	0.38 × 0.32 × 0.24 mm
β = 110.486 (9)°

Data collection top

Bruker SMART APEX CCD diffractometer	5212 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3266 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.982	R_int = 0.041
14295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
5212 reflections	Δρ_min = −0.15 e Å⁻³
305 parameters

Special details top

Experimental. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

18.7999 (0.0253) x + 6.0274 (0.0140) y + 4.7668 (0.0109) z = 7.5153 (0.0082)

* 0.0227 (0.0013) C4 * -0.0288 (0.0015) C5 * 0.0178 (0.0011) C6 * -0.0068 (0.0011) C8 * -0.0049 (0.0014) C9

Rms deviation of fitted atoms = 0.0186

- 0.7360 (0.0244) x + 15.4410 (0.0094) y - 3.1844 (0.0102) z = 8.2455 (0.0098)

Angle to previous plane (with approximate e.s.d.) = 81.53 (8)

* 0.0000 (0.0014) C10 * 0.0000 (0.0014) C11 * 0.0000 (0.0015) C12 * 0.0000 (0.0015) C13 * 0.0000 (0.0015) C14 * 0.0000 (0.0015) C15

Rms deviation of fitted atoms = 0.0000

6.5144 (0.0251) x + 11.2780 (0.0120) y - 8.6296 (0.0089) z = 7.8493 (0.0106)

Angle to previous plane (with approximate e.s.d.) = 30.67 (9)

* 0.0000 (0.0015) C18 * 0.0000 (0.0015) C19 * 0.0000 (0.0015) C20 * 0.0000 (0.0015) C21 * 0.0000 (0.0015) C22 * 0.0000 (0.0016) C23

Rms deviation of fitted atoms = 0.0000

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	Occ. (<1)
C1	0.21676 (7)	0.42190 (12)	0.10641 (17)	0.0398 (4)
C2	0.23258 (7)	0.43944 (11)	0.01610 (16)	0.0384 (4)
C3	0.23849 (7)	0.52781 (11)	−0.02193 (17)	0.0380 (4)
H3A	0.2253	0.5299	−0.1086	0.046*
C4	0.20768 (7)	0.58404 (12)	0.02376 (16)	0.0363 (4)
C5	0.19297 (7)	0.66544 (12)	−0.03195 (18)	0.0426 (5)
C6	0.16490 (8)	0.72255 (13)	0.01636 (17)	0.0467 (5)
H6A	0.1315	0.7258	−0.0399	0.056*
H6B	0.1793	0.7773	0.0216	0.056*
C7	0.16233 (7)	0.70135 (12)	0.13490 (18)	0.0432 (5)
H7A	0.1946	0.7191	0.1892	0.052*
C8	0.16176 (8)	0.61261 (13)	0.16256 (19)	0.0480 (5)
H8A	0.1280	0.5929	0.1333	0.058*
H8B	0.1744	0.6055	0.2478	0.058*
C9	0.19168 (7)	0.56133 (12)	0.10981 (16)	0.0378 (4)
C10	0.29243 (7)	0.55177 (11)	0.01855 (18)	0.0396 (4)
C11	0.31728 (7)	0.57684 (13)	0.13438 (17)	0.0443 (5)
H11A	0.3000	0.5865	0.1850	0.053*
C12	0.36802 (8)	0.58754 (13)	0.17454 (19)	0.0473 (5)
C13	0.39391 (8)	0.57317 (13)	0.0989 (2)	0.0505 (5)
C14	0.36906 (8)	0.54809 (14)	−0.0170 (2)	0.0544 (6)
H14A	0.3864	0.5385	−0.0676	0.065*
C15	0.31832 (8)	0.53739 (13)	−0.05712 (19)	0.0484 (5)
H15A	0.3017	0.5206	−0.1346	0.058*
C16	0.37141 (7)	0.65844 (12)	0.35114 (17)	0.0418 (5)
H16A	0.3953	0.6784	0.4234	0.063*
H16B	0.3489	0.6218	0.3691	0.063*
H16C	0.3536	0.7044	0.3056	0.063*
C17	0.47282 (7)	0.55420 (13)	0.08253 (18)	0.0442 (5)
H17A	0.5070	0.5570	0.1308	0.066*
H17B	0.4667	0.5891	0.0145	0.066*
H17C	0.4643	0.4981	0.0574	0.066*
C18	0.12798 (8)	0.75372 (13)	0.17207 (18)	0.0465 (5)
C19	0.15023 (8)	0.80989 (13)	0.26227 (18)	0.0444 (5)
H19A	0.1843	0.8140	0.2934	0.053*
C20	0.12148 (7)	0.85989 (12)	0.30591 (19)	0.0453 (5)
H20A	0.1364	0.8975	0.3663	0.054*
C21	0.07048 (7)	0.85373 (12)	0.25936 (17)	0.0425 (5)
H21C	0.0512	0.8872	0.2886	0.051*
C22	0.04824 (8)	0.79756 (12)	0.16916 (18)	0.0448 (5)
H22A	0.0141	0.7934	0.1380	0.054*
C23	0.07698 (7)	0.74756 (12)	0.12551 (18)	0.0459 (5)
H23A	0.0621	0.7100	0.0652	0.055*
C24	0.24929 (7)	0.37408 (12)	−0.03676 (18)	0.0424 (5)
N1	0.21337 (6)	0.34897 (10)	0.15312 (15)	0.0438 (4)
H1A	0.2221	0.3049	0.1256	0.053*
H1B	0.2025	0.3455	0.2108	0.053*
N2	0.26326 (6)	0.32244 (10)	−0.08241 (14)	0.0418 (4)
O1	0.20008 (5)	0.48364 (8)	0.16179 (11)	0.0403 (3)
O2	0.20311 (5)	0.68522 (9)	−0.11773 (12)	0.0473 (4)
O3	0.39552 (5)	0.61541 (9)	0.28562 (13)	0.0495 (4)
O4	0.44392 (5)	0.58132 (9)	0.14876 (12)	0.0461 (4)
O1W	1.0000	0.7117 (3)	0.7500	0.0600 (13)	0.50
H1X	1.0148	0.6920	0.7062	0.072*	0.25
H1Y	0.9771	0.7439	0.7095	0.072*	0.25
O2W	0.0778 (2)	0.4029 (3)	0.9183 (5)	0.0473 (14)	0.25
H2X	0.0654	0.3666	0.8652	0.057*	0.25
H2Y	0.1088	0.4040	0.9360	0.057*	0.25
O3W	0.0547 (2)	0.5322 (3)	0.9458 (5)	0.0514 (15)	0.25
H3X	0.0710	0.5671	0.9215	0.062*	0.25
H3Y	0.0242	0.5384	0.9073	0.062*	0.25
O6W	0.0707 (2)	0.4226 (4)	0.1806 (5)	0.0497 (14)	0.25
H6X	0.0635	0.3823	0.1323	0.060*	0.25
H6Y	0.0502	0.4617	0.1534	0.060*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0460 (10)	0.0365 (10)	0.0360 (10)	0.0014 (8)	0.0133 (9)	−0.0021 (8)
C2	0.0469 (10)	0.0295 (10)	0.0356 (10)	0.0015 (8)	0.0104 (8)	−0.0028 (8)
C3	0.0469 (11)	0.0321 (10)	0.0340 (10)	0.0026 (8)	0.0128 (8)	−0.0016 (7)
C4	0.0419 (10)	0.0344 (10)	0.0347 (9)	0.0029 (7)	0.0160 (8)	−0.0021 (7)
C5	0.0405 (11)	0.0430 (11)	0.0445 (11)	0.0090 (8)	0.0151 (8)	0.0079 (9)
C6	0.0482 (11)	0.0503 (12)	0.0446 (11)	0.0153 (10)	0.0201 (9)	0.0186 (10)
C7	0.0422 (11)	0.0415 (11)	0.0448 (11)	0.0168 (8)	0.0139 (8)	0.0143 (9)
C8	0.0563 (12)	0.0423 (11)	0.0430 (11)	0.0111 (10)	0.0143 (10)	−0.0020 (9)
C9	0.0457 (10)	0.0342 (10)	0.0344 (10)	0.0055 (8)	0.0150 (8)	0.0038 (8)
C10	0.0444 (10)	0.0297 (9)	0.0435 (11)	0.0058 (8)	0.0137 (8)	0.0020 (8)
C11	0.0492 (12)	0.0476 (11)	0.0361 (10)	0.0030 (9)	0.0148 (9)	0.0001 (9)
C12	0.0493 (12)	0.0464 (12)	0.0418 (11)	0.0014 (9)	0.0103 (9)	−0.0018 (9)
C13	0.0478 (12)	0.0436 (12)	0.0585 (13)	0.0009 (9)	0.0165 (10)	0.0011 (10)
C14	0.0521 (13)	0.0503 (13)	0.0574 (14)	0.0013 (10)	0.0150 (10)	−0.0005 (11)
C15	0.0556 (13)	0.0463 (12)	0.0424 (12)	0.0019 (10)	0.0158 (10)	−0.0002 (9)
C16	0.0407 (11)	0.0431 (11)	0.0379 (10)	−0.0079 (9)	0.0092 (8)	−0.0167 (9)
C17	0.0443 (11)	0.0435 (11)	0.0435 (11)	0.0085 (9)	0.0135 (8)	0.0054 (9)
C18	0.0489 (11)	0.0468 (12)	0.0452 (11)	0.0134 (9)	0.0181 (9)	0.0103 (9)
C19	0.0398 (10)	0.0470 (12)	0.0472 (11)	0.0114 (9)	0.0164 (8)	0.0038 (10)
C20	0.0440 (11)	0.0395 (11)	0.0494 (12)	0.0021 (9)	0.0128 (9)	−0.0149 (9)
C21	0.0437 (12)	0.0444 (12)	0.0411 (11)	0.0141 (9)	0.0172 (9)	−0.0048 (9)
C22	0.0438 (10)	0.0490 (12)	0.0429 (10)	0.0120 (9)	0.0170 (8)	−0.0163 (9)
C23	0.0494 (12)	0.0411 (10)	0.0467 (11)	0.0047 (8)	0.0160 (9)	−0.0200 (9)
C24	0.0502 (11)	0.0358 (10)	0.0411 (11)	0.0023 (9)	0.0156 (9)	−0.0006 (9)
N1	0.0407 (9)	0.0338 (9)	0.0551 (11)	0.0082 (7)	0.0145 (8)	0.0036 (8)
N2	0.0461 (10)	0.0416 (9)	0.0376 (9)	0.0023 (7)	0.0148 (7)	−0.0069 (7)
O1	0.0436 (7)	0.0341 (7)	0.0434 (8)	0.0108 (6)	0.0156 (6)	0.0040 (6)
O2	0.0504 (8)	0.0517 (9)	0.0410 (7)	0.0151 (7)	0.0176 (6)	0.0185 (7)
O3	0.0513 (8)	0.0417 (8)	0.0515 (9)	0.0009 (6)	0.0131 (7)	−0.0146 (7)
O4	0.0443 (8)	0.0452 (8)	0.0474 (8)	0.0000 (6)	0.0143 (6)	−0.0122 (7)
O1W	0.054 (2)	0.052 (3)	0.048 (2)	0.000	−0.0156 (19)	0.000
O2W	0.043 (3)	0.055 (4)	0.043 (3)	−0.021 (3)	0.014 (2)	−0.011 (3)
O3W	0.049 (3)	0.053 (3)	0.050 (3)	−0.016 (3)	0.013 (3)	−0.021 (3)
O6W	0.051 (3)	0.045 (3)	0.048 (3)	0.018 (3)	0.010 (3)	0.004 (3)

Geometric parameters (Å, º) top

C1—N1	1.324 (3)	C15—H15A	0.9300
C1—C2	1.352 (3)	C16—O3	1.409 (2)
C1—O1	1.379 (2)	C16—H16A	0.9600
C2—C24	1.404 (3)	C16—H16B	0.9600
C2—C3	1.527 (3)	C16—H16C	0.9600
C3—C4	1.507 (3)	C17—O4	1.415 (3)
C3—C10	1.517 (3)	C17—H17A	0.9600
C3—H3A	0.9800	C17—H17B	0.9600
C4—C9	1.329 (3)	C17—H17C	0.9600
C4—C5	1.470 (3)	C18—C19	1.390 (3)
C5—O2	1.214 (3)	C18—C23	1.390 (3)
C5—C6	1.478 (3)	C19—C20	1.390 (3)
C6—C7	1.498 (3)	C19—H19A	0.9300
C6—H6A	0.9700	C20—C21	1.390 (3)
C6—H6B	0.9700	C20—H20A	0.9300
C7—C8	1.473 (3)	C21—C22	1.390 (3)
C7—C18	1.491 (3)	C21—H21C	0.9300
C7—H7A	0.9800	C22—C23	1.390 (3)
C8—C9	1.494 (3)	C22—H22A	0.9300
C8—H8A	0.9700	C23—H23A	0.9300
C8—H8B	0.9700	C24—N2	1.149 (3)
C9—O1	1.385 (2)	N1—H1A	0.8601
C10—C11	1.390 (3)	N1—H1B	0.8607
C10—C15	1.390 (3)	O1W—H1X	0.8500
C11—C12	1.390 (3)	O1W—H1Y	0.8500
C11—H11A	0.9300	O2W—H2X	0.8501
C12—O3	1.374 (2)	O2W—H2Y	0.8499
C12—C13	1.390 (3)	O3W—H3X	0.8499
C13—O4	1.369 (3)	O3W—H3Y	0.8500
C13—C14	1.390 (3)	O6W—H6X	0.8500
C14—C15	1.390 (3)	O6W—H6Y	0.8501
C14—H14A	0.9300

N1—C1—C2	128.76 (18)	O4—C13—C14	124.6 (2)
N1—C1—O1	110.24 (18)	C12—C13—C14	120.0 (2)
C2—C1—O1	120.99 (18)	C15—C14—C13	120.0 (2)
C1—C2—C24	118.50 (18)	C15—C14—H14A	120.0
C1—C2—C3	122.92 (17)	C13—C14—H14A	120.0
C24—C2—C3	118.22 (18)	C14—C15—C10	120.0 (2)
C4—C3—C10	113.91 (15)	C14—C15—H15A	120.0
C4—C3—C2	108.04 (17)	C10—C15—H15A	120.0
C10—C3—C2	110.68 (15)	O3—C16—H16A	109.5
C4—C3—H3A	108.0	O3—C16—H16B	109.5
C10—C3—H3A	108.0	H16A—C16—H16B	109.5
C2—C3—H3A	108.0	O3—C16—H16C	109.5
C9—C4—C5	118.64 (18)	H16A—C16—H16C	109.5
C9—C4—C3	122.25 (18)	H16B—C16—H16C	109.5
C5—C4—C3	119.06 (17)	O4—C17—H17A	109.5
O2—C5—C4	120.47 (18)	O4—C17—H17B	109.5
O2—C5—C6	120.24 (18)	H17A—C17—H17B	109.5
C4—C5—C6	119.28 (18)	O4—C17—H17C	109.5
C5—C6—C7	116.90 (16)	H17A—C17—H17C	109.5
C5—C6—H6A	108.1	H17B—C17—H17C	109.5
C7—C6—H6A	108.1	C19—C18—C23	120.00 (19)
C5—C6—H6B	108.1	C19—C18—C7	115.45 (19)
C7—C6—H6B	108.1	C23—C18—C7	124.5 (2)
H6A—C6—H6B	107.3	C20—C19—C18	120.0 (2)
C8—C7—C18	114.96 (19)	C20—C19—H19A	120.0
C8—C7—C6	116.55 (18)	C18—C19—H19A	120.0
C18—C7—C6	114.81 (16)	C19—C20—C21	120.00 (19)
C8—C7—H7A	102.5	C19—C20—H20A	120.0
C18—C7—H7A	102.5	C21—C20—H20A	120.0
C6—C7—H7A	102.5	C22—C21—C20	120.00 (18)
C7—C8—C9	112.86 (19)	C22—C21—H21C	120.0
C7—C8—H8A	109.0	C20—C21—H21C	120.0
C9—C8—H8A	109.0	C21—C22—C23	120.0 (2)
C7—C8—H8B	109.0	C21—C22—H22A	120.0
C9—C8—H8B	109.0	C23—C22—H22A	120.0
H8A—C8—H8B	107.8	C22—C23—C18	120.00 (19)
C4—C9—O1	123.35 (18)	C22—C23—H23A	120.0
C4—C9—C8	126.45 (18)	C18—C23—H23A	120.0
O1—C9—C8	110.19 (16)	N2—C24—C2	177.8 (2)
C11—C10—C15	120.00 (19)	C1—N1—H1A	119.7
C11—C10—C3	120.77 (19)	C1—N1—H1B	120.3
C15—C10—C3	118.65 (18)	H1A—N1—H1B	119.9
C12—C11—C10	120.0 (2)	C1—O1—C9	118.10 (15)
C12—C11—H11A	120.0	C12—O3—C16	118.45 (17)
C10—C11—H11A	120.0	C13—O4—C17	117.90 (16)
O3—C12—C11	124.3 (2)	H1X—O1W—H1Y	109.5
O3—C12—C13	115.7 (2)	H2X—O2W—H2Y	109.5
C11—C12—C13	120.0 (2)	H3X—O3W—H3Y	109.5
O4—C13—C12	115.35 (19)	H6X—O6W—H6Y	109.5

N1—C1—C2—C24	−1.8 (3)	C10—C11—C12—O3	177.15 (19)
O1—C1—C2—C24	179.83 (17)	C10—C11—C12—C13	0.0 (3)
N1—C1—C2—C3	−174.77 (19)	O3—C12—C13—O4	5.8 (3)
O1—C1—C2—C3	6.8 (3)	C11—C12—C13—O4	−176.76 (18)
C1—C2—C3—C4	−20.2 (2)	O3—C12—C13—C14	−177.39 (18)
C24—C2—C3—C4	166.75 (16)	C11—C12—C13—C14	0.0 (3)
C1—C2—C3—C10	105.1 (2)	O4—C13—C14—C15	176.4 (2)
C24—C2—C3—C10	−67.9 (2)	C12—C13—C14—C15	0.0 (3)
C10—C3—C4—C9	−105.4 (2)	C13—C14—C15—C10	0.0 (3)
C2—C3—C4—C9	18.0 (2)	C11—C10—C15—C14	0.0 (3)
C10—C3—C4—C5	77.3 (2)	C3—C10—C15—C14	−171.30 (18)
C2—C3—C4—C5	−159.31 (16)	C8—C7—C18—C19	112.6 (2)
C9—C4—C5—O2	−173.29 (19)	C6—C7—C18—C19	−108.0 (2)
C3—C4—C5—O2	4.1 (3)	C8—C7—C18—C23	−65.3 (3)
C9—C4—C5—C6	5.6 (3)	C6—C7—C18—C23	74.0 (3)
C3—C4—C5—C6	−176.94 (18)	C23—C18—C19—C20	0.0 (3)
O2—C5—C6—C7	−168.38 (19)	C7—C18—C19—C20	−178.03 (19)
C4—C5—C6—C7	12.7 (3)	C18—C19—C20—C21	0.0 (3)
C5—C6—C7—C8	−33.1 (3)	C19—C20—C21—C22	0.0 (3)
C5—C6—C7—C18	−171.76 (19)	C20—C21—C22—C23	0.0 (3)
C18—C7—C8—C9	172.45 (17)	C21—C22—C23—C18	0.0 (3)
C6—C7—C8—C9	33.8 (3)	C19—C18—C23—C22	0.0 (3)
C5—C4—C9—O1	174.74 (16)	C7—C18—C23—C22	177.85 (19)
C3—C4—C9—O1	−2.6 (3)	C1—C2—C24—N2	−180 (100)
C5—C4—C9—C8	−3.7 (3)	C3—C2—C24—N2	−6 (6)
C3—C4—C9—C8	178.96 (18)	N1—C1—O1—C9	−167.40 (15)
C7—C8—C9—C4	−16.4 (3)	C2—C1—O1—C9	11.3 (3)
C7—C8—C9—O1	165.01 (15)	C4—C9—O1—C1	−13.7 (3)
C4—C3—C10—C11	41.8 (2)	C8—C9—O1—C1	165.00 (16)
C2—C3—C10—C11	−80.1 (2)	C11—C12—O3—C16	−19.5 (3)
C4—C3—C10—C15	−146.95 (18)	C13—C12—O3—C16	157.75 (19)
C2—C3—C10—C15	91.1 (2)	C12—C13—O4—C17	169.62 (18)
C15—C10—C11—C12	0.0 (3)	C14—C13—O4—C17	−7.0 (3)
C3—C10—C11—C12	171.12 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.20	3.042 (3)	167
N1—H1B···O2ⁱⁱ	0.86	2.12	2.935 (3)	158

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂O₄·H₂O
M_r	420.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	29.008 (16), 16.146 (8), 12.068 (6)
β (°)	110.486 (9)
V (Å³)	5295 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.32 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.972, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	14295, 5212, 3266
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.132, 1.00
No. of reflections	5212
No. of parameters	305
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.20	3.042 (3)	166.6
N1—H1B···O2ⁱⁱ	0.86	2.12	2.935 (3)	157.5

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

Acknowledgements

This work was supported by the National Major Fundamental Research Program of China (grant No. 2009CB522802), the Major Program of the National Natural Significant Drug Discovery (grant No. 2009ZX09502–015) National Key Technologies Program of China during the 11th Five-Year Plan Period, the Postdoctoral Innovative Projects of Shandong (grant No. 200801002) and the National TCM Project Application in the 11th Five-Year Period (grant No. 2008BAI51B02).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Foroumadi, A., Dehghan, G., Samzadeh-Kermani, A., Arabsorkhi, F., Sorkhi, M., Shafiee, A. & Abodollahi, M. (2007). Asian J. Chem. 19, 1391–1396. CAS Google Scholar
Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S.-X., Drewe, J., Labrecque, D., Kasibhatla, S. & Tseng, B. (2004). Mol. Cancer Ther. 3, 1375–1384. Web of Science PubMed CAS Google Scholar
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Crogan-Grundy, C., Labreque, D., Bubenick, M., Attardo, G., Denis, R., Lamothe, S., Gourdeau, H., Tseng, B., Kasibhatla, S. & Cai, S. X. (2008). J. Med. Chem. 51, 417–423. Web of Science CrossRef PubMed CAS Google Scholar
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y., Zhao, J., Jia, S., Herich, J., Labreque, D., Storer, R., Meerovitch, K., Bouffard, D., Rej, R., Denis, R., Blais, C., Lamothe, S., Attardo, G., Gourdeau, H., Tseng, B., Kasibhatla, S. & Cai, S. X. (2004). J. Med. Chem. 47, 6299–6310. Web of Science CrossRef PubMed CAS Google Scholar
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Zhao, J., Crogan-Grundy, C., Xu, L., Lamothe, S., Gourdeau, H., Denis, R., Tseng, B., Kasibhatla, S. & Cai, S. X. (2007). J. Med. Chem. 50, 2858–2864. Web of Science CrossRef PubMed CAS Google Scholar
Kemnitzer, W., Kasibhatla, S., Jiang, S., Zhang, H., Zhao, J., Jia, S., Xu, L., Crogan-Grundy, C., Denis, R., Barriault, N., Vaillancourt, L., Charron, S., Dodd, J., Attardo, G., Labrecque, D., Lamothe, S., Gourdeau, H., Tseng, B., Drewe, J. & Cai, S. X. (2005). Bioorg. Med. Chem. Lett. 15, 4745–4751. Web of Science CrossRef PubMed CAS Google Scholar
Kidwai, M., Saxena, S., Rahman Khan, M. K. & Thukral, S. S. (2005). Bioorg. Med. Chem. Lett. 15, 4295–4298. Web of Science CrossRef PubMed CAS Google Scholar
Li, J. R., Zhang, L. J., Yang, X. Q., Li, Q., Wang, D., Wang, C. X., Shi, D. X. & Zhang, Q. (2008). Chin. Chem. Lett. 19, 15–18. Web of Science CrossRef CAS Google Scholar
Mahdavi, M., Davoodi, J., Zali, M. R. & Foroumadi, A. (2011). Biomed. Pharm. 65, 175–182. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, X. M., Wang, H. Y. & Li, S. L. (2006). J. Chem. Res. 12, 776–778. CrossRef Google Scholar
Yadav, J. S., Subba Reddy, B. V., Biswas, S. K. & Sengupta, S. (2009). Tetrahedron Lett. 50, 5798–5801. Web of Science CrossRef 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 68| Part 2| February 2012| Pages o409-o410

doi:10.1107/S1600536811056285

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

(4R,7S)-2-Amino-4-(3,4-dimeth­­oxy­phen­yl)-5-oxo-7-phenyl-5,6,7,8-tetra­hydro-4H-chromene-3-carbo­nitrile monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4R,7S)-2-Amino-4-(3,4-dimethoxyphenyl)-5-oxo-7-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile monohydrate