4,4′-Dianilino-3,3′-(4-chloro­benzyl­idene)bis­[furan-2(5H)-one]

Shi, F.; Zhou, D.-X.; Tu, S.-J.

doi:10.1107/S1600536809021084

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1513-o1514

doi:10.1107/S1600536809021084

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4,4′-Dianilino-3,3′-(4-chlorobenzylidene)bis[furan-2(5H)-one]

Feng Shi,^a Dian-Xiang Zhou ^a and Shu-Jiang Tu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 31 May 2009; accepted 3 June 2009; online 6 June 2009)

In the molecule of the title compound, C₂₇H₂₁ClN₂O₄, the dihedral angle between the furan rings is 67.00 (3)°. The chlorophenyl ring is oriented at dihedral angles of 76.61 (3) and 69.36 (3)° with respect to the furan rings. An intramolecular N—H⋯O interaction results in the formation of an eight-membered ring with a twisted conformation. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a three-dimensional network, forming R₂²(16) ring motifs. Three weak C—H⋯π interactions are also found.

Related literature

For the biological activity of tetronic acid derivatives and their metabolites, see: Altenbach et al. (2006 ); Foden et al. (1975 ); Ley et al. (1991 ); Roggo et al. (1994 ); Witiak et al. (1982 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₇H₂₁ClN₂O₄
M_r = 472.91
Monoclinic, P 2₁ /n
a = 10.973 (5) Å
b = 11.566 (5) Å
c = 17.795 (8) Å
β = 100.232 (7)°
V = 2222.6 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.28 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.975
11368 measured reflections
3913 independent reflections
1802 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.251
S = 1.03
3913 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.05	2.797 (3)	145
N2—H2⋯O2ⁱ	0.86	2.09	2.907 (3)	158
C4—H4A⋯O4ⁱⁱ	0.97	2.24	3.206 (3)	178
C8—H8A⋯Cg5ⁱⁱⁱ	0.97	2.98	3.721 (3)	134
C8—H8B⋯Cg4^iv	0.97	2.91	3.617 (3)	131
C19—H19⋯Cg3^v	0.93	2.90	3.766 (3)	156
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg3, Cg4 and Cg5 are the centroids of the C10–C15, C16–C21 and C22–C27 rings, respectively.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021084/hk2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021084/hk2705Isup2.hkl

checkCIF report

Comment top

Tetronic acid derivatives and their metabolites have gained much attention from synthetic and medicinal chemists because of their prominent antibiotic (Ley et al., 1991), antico-agulant (Witiak et al., 1982), anti-inflammatory (Foden et al., 1975) and anti-HIV (Roggo et al., 1994) activities. Among them, open-chain derivatives of bistetronic acid, which contain two tetronic acid skeletons in one molecule, may display important pharmacological activities (Altenbach et al., 2006). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (O1/C1-C4), B (O3/C5-C8), C (C10-C15), D (C16-C21) and E (C22-C27) are, of course, planar. The dihedral angles between them are A/B = 67.00 (3), A/C = 76.61 (3), B/C = 69.36 (3), A/D = 14.64 (3) and B/E = 32.61 (3) °. Intramolecular N-H···O interaction (Table 1) results in the formation of an eight-membered ring F (O4/N1/C2/C3/C5/C6/C9/H1), having twisted conformation.

In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a three-dimensional network forming R₂²(16) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. There also exist three weak C—H···π interactions (Table 1).

Related literature top

For the biologicalbiological activity of tetronic acid derivatives and their metabolites, see: Altenbach et al. (2006); Foden et al. (1975); Ley et al. (1991); Roggo et al. (1994); Witiak et al. (1982). For bond-length data, see: Allen et al. (1987). For hydrogen-bond ring motifs, see: Bernstein et al. (1995). Cg3, Cg4 and Cg5 are the centroids of the C10–C15, C16–C21 and C22–C27 rings, respectively.

Experimental top

The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.5 mmol) with 4-phenylamino-2,5-dihydrofuran-2-one (1 mmol) in glycol at 373 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 10 min (yield; 92%, m.p. 508–509 K). Crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

4,4'-Dianilino-3,3'-(4-chlorobenzylidene)bis[furan-2(5H)-one] top

Crystal data top

C₂₇H₂₁ClN₂O₄	F(000) = 984
M_r = 472.91	D_x = 1.413 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 508–509 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.973 (5) Å	Cell parameters from 1079 reflections
b = 11.566 (5) Å	θ = 2.4–19.9°
c = 17.795 (8) Å	µ = 0.21 mm⁻¹
β = 100.232 (7)°	T = 298 K
V = 2222.6 (17) Å³	Block, yellow
Z = 4	0.28 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3913 independent reflections
Radiation source: fine-focus sealed tube	1802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.943, T_max = 0.975	k = −13→13
11368 measured reflections	l = −11→21

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.251	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²)]
3913 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₇H₂₁ClN₂O₄	V = 2222.6 (17) Å³
M_r = 472.91	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.973 (5) Å	µ = 0.21 mm⁻¹
b = 11.566 (5) Å	T = 298 K
c = 17.795 (8) Å	0.28 × 0.15 × 0.12 mm
β = 100.232 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3913 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1802 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.975	R_int = 0.087
11368 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.251	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3913 reflections	Δρ_min = −0.28 e Å⁻³
307 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
Cl1	0.72987 (15)	0.38409 (13)	0.15930 (11)	0.0740 (6)
O1	0.5201 (3)	1.0941 (3)	0.2030 (2)	0.0537 (10)
O2	0.5296 (3)	1.0511 (3)	0.0810 (2)	0.0620 (11)
O3	0.0934 (3)	0.7208 (3)	0.0853 (2)	0.0498 (10)
O4	0.2460 (3)	0.6755 (3)	0.1814 (2)	0.0502 (10)
N1	0.3811 (4)	0.8428 (4)	0.2747 (3)	0.0503 (12)
H1	0.3691	0.7767	0.2525	0.060*
N2	0.2308 (4)	0.9098 (4)	−0.0373 (3)	0.0517 (12)
H2	0.3081	0.9226	−0.0367	0.062*
C1	0.5027 (5)	1.0208 (4)	0.1418 (4)	0.0487 (14)
C2	0.4502 (4)	0.9143 (4)	0.1609 (3)	0.0385 (12)
C3	0.4320 (4)	0.9225 (4)	0.2347 (3)	0.0388 (12)
C4	0.4770 (5)	1.0372 (4)	0.2651 (3)	0.0458 (13)
H4A	0.4105	1.0809	0.2810	0.055*
H4B	0.5438	1.0287	0.3085	0.055*
C5	0.2134 (4)	0.7262 (4)	0.1207 (3)	0.0407 (13)
C6	0.2842 (4)	0.7961 (4)	0.0774 (3)	0.0384 (12)
C7	0.2060 (4)	0.8381 (4)	0.0164 (3)	0.0414 (13)
C8	0.0777 (4)	0.7922 (5)	0.0181 (3)	0.0482 (14)
H8A	0.0203	0.8548	0.0217	0.058*
H8B	0.0473	0.7471	−0.0273	0.058*
C9	0.4220 (4)	0.8188 (4)	0.1024 (3)	0.0403 (13)
H9	0.4504	0.8481	0.0567	0.048*
C10	0.4950 (4)	0.7072 (4)	0.1233 (3)	0.0379 (12)
C11	0.4592 (5)	0.6052 (4)	0.0851 (3)	0.0508 (15)
H11	0.3858	0.6039	0.0497	0.061*
C12	0.5286 (5)	0.5052 (5)	0.0977 (3)	0.0560 (15)
H12	0.5015	0.4371	0.0723	0.067*
C13	0.6382 (5)	0.5084 (4)	0.1484 (3)	0.0474 (14)
C14	0.6747 (5)	0.6063 (5)	0.1892 (3)	0.0526 (15)
H14	0.7467	0.6066	0.2258	0.063*
C15	0.6030 (4)	0.7050 (5)	0.1754 (3)	0.0469 (14)
H15	0.6290	0.7720	0.2024	0.056*
C16	0.3439 (5)	0.8482 (4)	0.3466 (3)	0.0442 (13)
C17	0.2643 (5)	0.7626 (5)	0.3627 (3)	0.0541 (15)
H17	0.2386	0.7049	0.3270	0.065*
C18	0.2233 (6)	0.7624 (5)	0.4310 (4)	0.0669 (18)
H18	0.1689	0.7049	0.4408	0.080*
C19	0.2606 (5)	0.8448 (5)	0.4849 (4)	0.0625 (17)
H19	0.2332	0.8430	0.5315	0.075*
C20	0.3380 (5)	0.9292 (5)	0.4697 (3)	0.0584 (16)
H20	0.3625	0.9862	0.5060	0.070*
C21	0.3816 (5)	0.9328 (5)	0.4016 (3)	0.0526 (15)
H21	0.4356	0.9911	0.3925	0.063*
C22	0.1487 (5)	0.9681 (5)	−0.0949 (3)	0.0485 (14)
C23	0.0411 (6)	0.9218 (5)	−0.1334 (4)	0.0694 (19)
H23	0.0189	0.8469	−0.1224	0.083*
C24	−0.0353 (6)	0.9854 (6)	−0.1886 (4)	0.0719 (19)
H24	−0.1087	0.9525	−0.2137	0.086*
C25	−0.0056 (6)	1.0951 (5)	−0.2070 (4)	0.0646 (17)
H25	−0.0576	1.1376	−0.2439	0.078*
C26	0.1045 (6)	1.1405 (5)	−0.1688 (4)	0.0619 (17)
H26	0.1276	1.2147	−0.1806	0.074*
C27	0.1799 (5)	1.0788 (5)	−0.1142 (3)	0.0543 (15)
H27	0.2536	1.1116	−0.0895	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0781 (11)	0.0616 (10)	0.0802 (14)	0.0182 (8)	0.0080 (10)	0.0048 (9)
O1	0.063 (2)	0.047 (2)	0.054 (3)	−0.0074 (18)	0.020 (2)	−0.006 (2)
O2	0.068 (3)	0.067 (3)	0.057 (3)	−0.015 (2)	0.027 (2)	0.007 (2)
O3	0.039 (2)	0.059 (2)	0.049 (2)	−0.0080 (16)	0.0042 (19)	0.011 (2)
O4	0.055 (2)	0.059 (2)	0.037 (2)	−0.0088 (17)	0.0071 (19)	0.0074 (19)
N1	0.067 (3)	0.047 (3)	0.041 (3)	−0.008 (2)	0.020 (3)	−0.007 (2)
N2	0.039 (2)	0.063 (3)	0.051 (3)	−0.001 (2)	0.002 (2)	0.018 (3)
C1	0.043 (3)	0.047 (3)	0.059 (4)	−0.001 (2)	0.016 (3)	0.001 (3)
C2	0.026 (2)	0.056 (3)	0.033 (3)	−0.002 (2)	0.003 (2)	−0.003 (3)
C3	0.035 (3)	0.041 (3)	0.041 (3)	−0.001 (2)	0.007 (3)	0.001 (3)
C4	0.050 (3)	0.052 (3)	0.037 (3)	0.000 (3)	0.013 (3)	−0.002 (3)
C5	0.034 (3)	0.048 (3)	0.040 (3)	−0.004 (2)	0.005 (3)	−0.004 (3)
C6	0.033 (2)	0.046 (3)	0.036 (3)	−0.003 (2)	0.005 (2)	−0.003 (3)
C7	0.042 (3)	0.045 (3)	0.038 (3)	−0.004 (2)	0.008 (3)	−0.002 (3)
C8	0.040 (3)	0.058 (3)	0.045 (4)	−0.006 (2)	0.003 (3)	0.007 (3)
C9	0.033 (3)	0.051 (3)	0.037 (3)	−0.007 (2)	0.006 (2)	−0.001 (3)
C10	0.039 (3)	0.045 (3)	0.029 (3)	−0.002 (2)	0.005 (2)	−0.007 (3)
C11	0.041 (3)	0.065 (4)	0.041 (4)	−0.004 (3)	−0.009 (3)	−0.010 (3)
C12	0.054 (3)	0.058 (4)	0.054 (4)	0.001 (3)	0.003 (3)	−0.011 (3)
C13	0.048 (3)	0.045 (3)	0.049 (4)	0.002 (2)	0.008 (3)	0.000 (3)
C14	0.041 (3)	0.069 (4)	0.044 (4)	−0.002 (3)	−0.005 (3)	−0.001 (3)
C15	0.042 (3)	0.051 (3)	0.047 (4)	−0.004 (3)	0.004 (3)	−0.009 (3)
C16	0.051 (3)	0.050 (3)	0.032 (3)	0.005 (3)	0.009 (3)	0.003 (3)
C17	0.058 (3)	0.064 (4)	0.041 (4)	−0.015 (3)	0.011 (3)	−0.004 (3)
C18	0.070 (4)	0.077 (4)	0.058 (5)	−0.013 (3)	0.023 (4)	−0.002 (4)
C19	0.064 (4)	0.083 (4)	0.041 (4)	0.005 (3)	0.010 (3)	0.008 (4)
C20	0.071 (4)	0.064 (4)	0.039 (4)	0.007 (3)	0.005 (3)	−0.004 (3)
C21	0.061 (4)	0.056 (3)	0.040 (4)	−0.009 (3)	0.007 (3)	−0.005 (3)
C22	0.051 (3)	0.054 (3)	0.039 (3)	0.001 (3)	0.004 (3)	0.005 (3)
C23	0.065 (4)	0.063 (4)	0.068 (5)	−0.020 (3)	−0.020 (4)	0.014 (4)
C24	0.060 (4)	0.087 (5)	0.061 (5)	−0.016 (3)	−0.013 (4)	0.009 (4)
C25	0.060 (4)	0.072 (4)	0.058 (4)	0.014 (3)	0.002 (3)	0.010 (4)
C26	0.070 (4)	0.055 (4)	0.061 (4)	0.002 (3)	0.012 (4)	0.007 (3)
C27	0.051 (3)	0.060 (4)	0.051 (4)	0.000 (3)	0.004 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.745 (5)	C11—H11	0.9300
O1—C1	1.366 (6)	C12—C13	1.369 (7)
O1—C4	1.436 (6)	C12—H12	0.9300
O2—C1	1.223 (6)	C13—C14	1.367 (7)
O3—C5	1.357 (6)	C14—C15	1.383 (7)
O3—C8	1.439 (6)	C14—H14	0.9300
O4—C5	1.224 (6)	C15—H15	0.9300
N1—C3	1.345 (6)	C16—C17	1.384 (7)
N1—C16	1.412 (6)	C16—C21	1.394 (7)
N1—H1	0.8600	C17—C18	1.369 (8)
N2—C7	1.329 (6)	C17—H17	0.9300
N2—C22	1.410 (6)	C18—C19	1.362 (8)
N2—H2	0.8600	C18—H18	0.9300
C1—C2	1.427 (7)	C19—C20	1.353 (8)
C2—C3	1.366 (7)	C19—H19	0.9300
C2—C9	1.512 (7)	C20—C21	1.381 (8)
C3—C4	1.484 (7)	C20—H20	0.9300
C4—H4A	0.9700	C21—H21	0.9300
C4—H4B	0.9700	C22—C23	1.365 (7)
C5—C6	1.436 (7)	C22—C27	1.385 (7)
C6—C7	1.349 (7)	C23—C24	1.384 (8)
C6—C9	1.522 (6)	C23—H23	0.9300
C7—C8	1.509 (6)	C24—C25	1.364 (8)
C8—H8A	0.9700	C24—H24	0.9300
C8—H8B	0.9700	C25—C26	1.381 (8)
C9—C10	1.530 (6)	C25—H25	0.9300
C9—H9	0.9800	C26—C27	1.360 (8)
C10—C15	1.369 (7)	C26—H26	0.9300
C10—C11	1.383 (6)	C27—H27	0.9300
C11—C12	1.381 (7)

C1—O1—C4	108.2 (4)	C10—C11—H11	118.8
C5—O3—C8	108.8 (4)	C13—C12—C11	118.6 (5)
C3—N1—C16	131.5 (5)	C13—C12—H12	120.7
C3—N1—H1	114.2	C11—C12—H12	120.7
C16—N1—H1	114.2	C14—C13—C12	120.9 (5)
C7—N2—C22	129.4 (4)	C14—C13—Cl1	121.0 (5)
C7—N2—H2	115.3	C12—C13—Cl1	118.2 (4)
C22—N2—H2	115.3	C13—C14—C15	119.0 (5)
O2—C1—O1	120.4 (5)	C13—C14—H14	120.5
O2—C1—C2	129.0 (5)	C15—C14—H14	120.5
O1—C1—C2	110.5 (5)	C10—C15—C14	122.2 (5)
C3—C2—C1	107.7 (5)	C10—C15—H15	118.9
C3—C2—C9	131.7 (5)	C14—C15—H15	118.9
C1—C2—C9	120.6 (5)	C17—C16—C21	118.5 (5)
N1—C3—C2	127.3 (5)	C17—C16—N1	116.8 (5)
N1—C3—C4	124.2 (5)	C21—C16—N1	124.7 (5)
C2—C3—C4	108.4 (4)	C18—C17—C16	120.3 (6)
O1—C4—C3	105.2 (4)	C18—C17—H17	119.8
O1—C4—H4A	110.7	C16—C17—H17	119.8
C3—C4—H4A	110.7	C19—C18—C17	121.3 (6)
O1—C4—H4B	110.7	C19—C18—H18	119.4
C3—C4—H4B	110.7	C17—C18—H18	119.4
H4A—C4—H4B	108.8	C20—C19—C18	118.9 (6)
O4—C5—O3	119.6 (4)	C20—C19—H19	120.5
O4—C5—C6	129.9 (5)	C18—C19—H19	120.5
O3—C5—C6	110.4 (5)	C19—C20—C21	121.8 (6)
C7—C6—C5	107.9 (4)	C19—C20—H20	119.1
C7—C6—C9	129.1 (5)	C21—C20—H20	119.1
C5—C6—C9	123.0 (5)	C20—C21—C16	119.2 (5)
N2—C7—C6	128.4 (5)	C20—C21—H21	120.4
N2—C7—C8	123.0 (5)	C16—C21—H21	120.4
C6—C7—C8	108.6 (5)	C23—C22—C27	117.9 (5)
O3—C8—C7	104.2 (4)	C23—C22—N2	124.2 (5)
O3—C8—H8A	110.9	C27—C22—N2	118.0 (5)
C7—C8—H8A	110.9	C22—C23—C24	120.6 (6)
O3—C8—H8B	110.9	C22—C23—H23	119.7
C7—C8—H8B	110.9	C24—C23—H23	119.7
H8A—C8—H8B	108.9	C25—C24—C23	121.6 (6)
C2—C9—C6	113.4 (4)	C25—C24—H24	119.2
C2—C9—C10	114.5 (4)	C23—C24—H24	119.2
C6—C9—C10	112.1 (4)	C24—C25—C26	117.4 (6)
C2—C9—H9	105.2	C24—C25—H25	121.3
C6—C9—H9	105.2	C26—C25—H25	121.3
C10—C9—H9	105.2	C27—C26—C25	121.3 (6)
C15—C10—C11	116.9 (5)	C27—C26—H26	119.3
C15—C10—C9	122.2 (4)	C25—C26—H26	119.3
C11—C10—C9	120.7 (4)	C26—C27—C22	121.1 (6)
C12—C11—C10	122.3 (5)	C26—C27—H27	119.4
C12—C11—H11	118.8	C22—C27—H27	119.4

C4—O1—C1—O2	178.2 (5)	C7—C6—C9—C10	−133.2 (5)
C4—O1—C1—C2	−0.8 (5)	C5—C6—C9—C10	49.9 (6)
O2—C1—C2—C3	−177.5 (5)	C2—C9—C10—C15	−20.6 (7)
O1—C1—C2—C3	1.3 (6)	C6—C9—C10—C15	−151.7 (5)
O2—C1—C2—C9	1.1 (8)	C2—C9—C10—C11	164.8 (4)
O1—C1—C2—C9	180.0 (4)	C6—C9—C10—C11	33.7 (7)
C16—N1—C3—C2	−170.5 (5)	C15—C10—C11—C12	−0.6 (8)
C16—N1—C3—C4	8.6 (8)	C9—C10—C11—C12	174.3 (5)
C1—C2—C3—N1	177.9 (5)	C10—C11—C12—C13	−1.7 (8)
C9—C2—C3—N1	−0.5 (9)	C11—C12—C13—C14	4.0 (8)
C1—C2—C3—C4	−1.3 (5)	C11—C12—C13—Cl1	−176.0 (4)
C9—C2—C3—C4	−179.7 (5)	C12—C13—C14—C15	−3.9 (8)
C1—O1—C4—C3	0.0 (5)	Cl1—C13—C14—C15	176.1 (4)
N1—C3—C4—O1	−178.4 (4)	C11—C10—C15—C14	0.8 (8)
C2—C3—C4—O1	0.9 (5)	C9—C10—C15—C14	−174.1 (5)
C8—O3—C5—O4	176.8 (5)	C13—C14—C15—C10	1.5 (8)
C8—O3—C5—C6	−2.7 (5)	C3—N1—C16—C17	162.7 (5)
O4—C5—C6—C7	−176.9 (5)	C3—N1—C16—C21	−17.4 (9)
O3—C5—C6—C7	2.5 (6)	C21—C16—C17—C18	0.6 (8)
O4—C5—C6—C9	0.5 (8)	N1—C16—C17—C18	−179.5 (5)
O3—C5—C6—C9	179.9 (4)	C16—C17—C18—C19	−0.9 (9)
C22—N2—C7—C6	−169.7 (5)	C17—C18—C19—C20	1.1 (9)
C22—N2—C7—C8	8.8 (9)	C18—C19—C20—C21	−1.1 (9)
C5—C6—C7—N2	177.4 (5)	C19—C20—C21—C16	0.8 (9)
C9—C6—C7—N2	0.2 (9)	C17—C16—C21—C20	−0.6 (8)
C5—C6—C7—C8	−1.2 (6)	N1—C16—C21—C20	179.6 (5)
C9—C6—C7—C8	−178.4 (5)	C7—N2—C22—C23	−37.0 (9)
C5—O3—C8—C7	1.9 (5)	C7—N2—C22—C27	143.6 (6)
N2—C7—C8—O3	−179.0 (5)	C27—C22—C23—C24	−1.5 (9)
C6—C7—C8—O3	−0.3 (6)	N2—C22—C23—C24	179.1 (6)
C3—C2—C9—C6	65.9 (7)	C22—C23—C24—C25	0.7 (10)
C1—C2—C9—C6	−112.3 (5)	C23—C24—C25—C26	0.5 (10)
C3—C2—C9—C10	−64.5 (7)	C24—C25—C26—C27	−0.8 (9)
C1—C2—C9—C10	117.3 (5)	C25—C26—C27—C22	−0.1 (9)
C7—C6—C9—C2	95.1 (7)	C23—C22—C27—C26	1.2 (9)
C5—C6—C9—C2	−81.7 (6)	N2—C22—C27—C26	−179.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.05	2.797 (3)	145
N2—H2···O2ⁱ	0.86	2.09	2.907 (3)	158
C4—H4A···O4ⁱⁱ	0.97	2.24	3.206 (3)	178
C8—H8A···Cg5ⁱⁱⁱ	0.97	2.98	3.721 (3)	134
C8—H8B···Cg4^iv	0.97	2.91	3.617 (3)	131
C19—H19···Cg3^v	0.93	2.90	3.766 (3)	156

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1/2, −y−1/2, z−1/2; (v) x−1/2, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁ClN₂O₄
M_r	472.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.973 (5), 11.566 (5), 17.795 (8)
β (°)	100.232 (7)
V (Å³)	2222.6 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11368, 3913, 1802
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.251, 1.03
No. of reflections	3913
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.05	2.797 (3)	145
N2—H2···O2ⁱ	0.86	2.09	2.907 (3)	158
C4—H4A···O4ⁱⁱ	0.97	2.24	3.206 (3)	178
C8—H8A···Cg5ⁱⁱⁱ	0.97	2.98	3.721 (3)	134
C8—H8B···Cg4^iv	0.97	2.91	3.617 (3)	131
C19—H19···Cg3^v	0.93	2.90	3.766 (3)	156

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1/2, −y−1/2, z−1/2; (v) x−1/2, −y−1/2, z−3/2.

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20672090), the Preliminary Item of Xuzhou Normal University on National Natural Science Foundation of China (grant No. 08XLY04) and the Science & Technology Foundation of Xuzhou City (grant No. XM08C027) for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altenbach, R. J., Brune, M. E., Buckner, S. A., Coghlan, M. J., Daza, A. V., Fabiyi, A., Gopalakrishnan, M., Henry, R. F., Khilevich, A., Kort, M. E., Milicic, I., Scott, V. E., Smith, J. C., Whiteaker, K. L. & Carroll, W. A. (2006). J. Med. Chem. 49, 6869–6887. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Foden, F. R., McCormick, J. & O'Mant, D. M. (1975). J. Med. Chem. 18, 199–203. CrossRef PubMed CAS Web of Science Google Scholar
Ley, S. V., Trudell, M. L. & Wadsworth, D. J. (1991). Tetrahedron, 47, 8285–8296. CrossRef CAS Web of Science Google Scholar
Roggo, B. E., Petersen, F., Delmendo, R., Jenny, H. B., Peter, H. H. & Roesel, J. (1994). J. Antibiot. 47, 136–142. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Witiak, D., Kokrady, S. S., Patel, S. T., Akbar, H., Feller, D. R. & Newmann, H. A. I. (1982). J. Med. Chem. 25, 90–93. CrossRef CAS PubMed Web of Science Google Scholar