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In the title compound, C23H26N2O4·H2O, the benzopyran ring system is planar. The piperazine ring adopts an almost perfect chair conformation, and the meth­oxy group is coplanar with its parent benzene ring. Hydrogen bonds link two water mol­ecules and two piperazine mol­ecules into tetra­meric units. The adjacent benzopyran moieties within these units also inter­act via π–π stacking inter­actions, and a sheet is formed by the propagation of these inter­actions. The bioassay results have shown α1-adrenoceptor antagonistic activity through in vitro animal experiments.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105040928/ln1189sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105040928/ln1189Isup2.hkl
Contains datablock I

CCDC reference: 299630

Comment top

Coumarin is the parent organic compound of a class of naturally occurring phytochemicals with fragrance found in many plant species, and these compounds have received significant attention for many years. Natural or synthetic compounds comprising a coumarin backbone have a wide range of biological activities, such as anti-inflammatory (Kontogiorgis & Hadjipavlou-Litina, 2005), antitumour (Dexeus et al., 1990), anti-allergic (Buckle et al., 1979) and anti-HIV-1 (Lunney et al., 1994) activities. Compounds possessing a piperazine ring are being studied extensively as potential psychotropic agents (Lopez-Rodriguez et al., 1999). The neuroleptic and anxiolytic (tranquilizer) properties of these compounds are due to their interaction with dopamine and serotonin receptors. According to the hypothetical views on the topography of the α1-adrenoceptor antagonists (Kenny et al., 1997; Bremner et al., 2000; Dardonville et al., 2000), the basic pharmaphore of an α1-adrenoceptor antagonist should include a basic nitrogen center (BNC), hydrophobic groups (HP), an aromatic ring (AR) linked to the BNC directly and a hydrogen-bond donor or receptor (HB). We have designed and synthesized a series of coumarin derivatives containing a piperazine ring on the basis of the abovementioned structure–activity relationships. The structure elucidation of these compounds is important for understanding the molecular mechanisms of their biological activity. However, reports about the crystal structures of this kind of compounds are scarce (Estrada et al., 2000). In this context, the crystal structure of the monohydrate of one of the prepared novel coumarin derivatives, viz. the title compound, (I), is reported.

A view of the molecular structure of compound (I) is shown in Fig. 1. The bond lengths and angles in (I) are comparable to the average values reported in the literature for atoms in similar environments (Allen et al., 1987). The benzopyran ring (O1/C1–C9) is planar, with a mean deviation of the constituent atoms from their least-squares plane of 0.006 Å. The molecule of (I) has a fully extended conformation, like its analogue trans-1-(2-methoxyphenyl)-4-[4-(2-phthalimido)cyclohexyl]piperazine (Dalpiaz et al., 1996). In (I), the dihedral angle between the plane of the phenyl ring and the least-squares plane of the piperazine ring is 17.42 (10)°, while Kuipers et al. (1997) reported that the angle between the plane of the benzene and piperazine rings in bis(N-{2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)-cis-2,6-dimethyl- 1-piperazinyl]ethyl}-4-fluorobenzenecarboxamide)fumarate is approximately 30°. In (I), the distances from the central N atom, N1, to the centroid of the phenyl ring, to the hydrogen-bond donor C23 and to the centroid of the coumarin moiety, the hydrophobic centre, are 5.689 (4), 9.265 (7) and 7.175 (4) Å, respectively. The corresponding distances reported by Li & Xia (2005) for α1-adrenoceptor antagonists are 5.82, 9.08 and 7.53 Å, respectively. The angle between the coumarin moiety and the phenyl ring, D, is 65.44 (8)° in (I) and 67.8° in the report by Paluchowska et al. (1999). The similarity between the key geometric parameters of (I) and those given by Paluchowska et al. (1999) and Li & Xia (2005) suggests that the title compound may have potential biological activity. Actually, the bioassay results for tests of the α1-adrenoceptor antagonistic activity of (I) through in vitro animal experiments in the New Drugs Screening Center of Jiangsu province of China have shown a slightly lower activity than prozosin, the most accepted positive control substance for α1-adrenoceptor antagonistic activity (Ford et al., 1994).

The piperazine ring adopts an almost perfect chair conformation, as in the case of N,N'-dimethylpiperazine (Parkin & Parsons, 2002). This is confirmed by the puckering parameters [Q = 0.566 (2) Å, q2 = 0.008 (2) Å, q3 = −0.566 (2) Å, θ = 180.0 (2)° and ϕ2 = 108 (14)°] for the atom sequence N1—C13—C14—N2—C15—C16 (Cremer & Pople, 1975) and the intra-ring torsion angles shown in Table 1. The N atoms are substituted in equatorial positions, which meets the requirements for the bioactive conformation of an α1-adrenoceptor antagonist (Kuipers et al., 1997). The length of the C17—N2 bond is somewhat shorter (Table 1) than that of the C12—N1 bond as a result of conjugation between atom N2 and the 4-methoxyphenyl ring to which it is bonded. The methoxy group is coplanar with ring D (Table 1).

The title compound crystallized as a monohydrate. Each water molecule donates two hydrogen bonds to two adjacent piperazine molecules (Table 2). These interactions link two water molecules and two piperazine molecules alternately across a centre of inversion into a tetrameric unit. The interactions that lead to this unit can be described by an overall graph-set motif of R44(26) (Bernstein et al., 1995; Desiraju, 1995). In addition, each water molecule accepts two soft C—H···O interactions (Desiraju, 1996) from two piperazine molecules not involved in the original tetramer, so that each water molecule is surrounded by four piperazine molecules (Fig. 2).

Additional ππ stacking interactions are present between the pyran ring (A; π-electron deficient) and the benzyl ring (B; π-electron rich) of the adjacent centrosymmetrically related (symmetry code: 2 − x, 1 − y, −z) benzopyran group within the hydrogen-bonded tetrameric unit (Fig. 3). The plane of ring A makes an angle of 0.38° with that of ring B of the opposing molecule and the two rings overlap with an intercentroid distance of 3.643 (3) Å. The perpendicular distance from the centre of gravity of each ring to the plane of the opposing ring is 3.50 Å with a slippage from the centroid of the opposing ring of 0.85 Å.

Experimental top

The synthesis of (I) was performed according to the method of Jain et al. (1967). A mixture of 7-bromoethoxy-4-methylcoumarin (566 mg, 2 mmol), 1-(4-methoxyphenyl)piperazine (457 mg, 2 mmol) and anhydrous K2CO3 (276 mg, 2 mmol) was stirred at reflux in acetone (5 ml) and anhydrous ethanol (5 ml) for 48 h. The precipitate was filtered off and washed with fresh chloroform. The solvent was evaporated under reduced pressure from the combined filtrate and washings. The residue was chromatographed on a silica gel column by eluting with a cyclohexane/acetone mixture (8:1 v/v) to give a colorless solid (170 mg, 21%, m.p 511 K); 1H NMR (500 MHz, CDCl3): δ 7.51 (d, 1H, H-5, J = 8.91 Hz), 6.95 (m, 4H, Ph), 6.86 (dd, 1H, H-6, J = 8.80 and 2.60 Hz), 6.82 (d, 1H, H-8, J = 2.60 Hz), 6.15 (s, 1H, H-3), 4.10 (t, 2H, CH2O, J = 6.30 Hz), 3.77 (s, 3H, OCH3), 3.10 [m, 4H, N4 (CH2)2], 2.85 [m, 4H, (CH2)2N1], 2.60 (m, 2H, N1CH2), 2.38 (s, 3H, CH3). A crystal suitable for diffraction analysis was obtained by slow evaporation of a solution of (I) in a mixture of ethanol and ethyl acetate (1:1 v/v) at room temperature.

Refinement top

The positions of the H atoms of the water molecule were located initially in a difference Fourier map and then constrained to ride on the parent O atom with Uiso(H) = 1.5Ueq(O). The methyl H atoms were constrained to an ideal geometry with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.93–0.97 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL and WinGX (Version 1.7; Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal packing of (I), showing the interactions involving the water molecule. Atoms marked with an asterisk (*), hash (#) or ampersand (&) are at the symmetry positions (2 − x, 1 − y, −z), (1/2 − x, y − 1/2, 1/2 − z) and (1 − x, 1 − y, −z), respectively. For clarity, some H atoms have been omitted.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of the stacked dimers via hydrogen bonds and ππ stacking interactions. Atoms marked with an asterisk (*) are at the symmetry positions (2 − x, 1 − y, −z). For clarity, some H atoms have been omitted.
7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one monohydrate top
Crystal data top
C23H26N2O4·H2OF(000) = 880
Mr = 412.47Dx = 1.305 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2841 reflections
a = 10.776 (7) Åθ = 2.2–24.1°
b = 7.483 (5) ŵ = 0.09 mm1
c = 26.381 (18) ÅT = 298 K
β = 99.406 (10)°Prism, colorless
V = 2099 (2) Å30.53 × 0.48 × 0.27 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3684 independent reflections
Radiation source: fine-focus sealed tube2296 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1210
Tmin = 0.962, Tmax = 0.985k = 88
10516 measured reflectionsl = 3131
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.055P)2 + 0.28P]
where P = (Fo2 + 2Fc2)/3
3684 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.17 e Å3
2 restraintsΔρmin = 0.22 e Å3
Crystal data top
C23H26N2O4·H2OV = 2099 (2) Å3
Mr = 412.47Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.776 (7) ŵ = 0.09 mm1
b = 7.483 (5) ÅT = 298 K
c = 26.381 (18) Å0.53 × 0.48 × 0.27 mm
β = 99.406 (10)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3684 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2296 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.985Rint = 0.038
10516 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0462 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.03Δρmax = 0.17 e Å3
3684 reflectionsΔρmin = 0.22 e Å3
273 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
xyzUiso*/Ueq
N10.53174 (16)0.7986 (2)0.12525 (6)0.0505 (5)
N20.31370 (15)0.8865 (2)0.17170 (6)0.0456 (4)
O11.17834 (14)0.76897 (18)0.00482 (5)0.0523 (4)
O21.36372 (17)0.7424 (2)0.02888 (6)0.0759 (5)
O30.80421 (14)0.8368 (2)0.05953 (6)0.0619 (4)
O40.15187 (14)0.9134 (2)0.23986 (6)0.0660 (5)
O50.47771 (17)0.4188 (2)0.09991 (7)0.0875 (6)
H5A0.49000.53420.10450.105*
H5B0.51270.40310.07280.105*
C11.2518 (2)0.7162 (3)0.04013 (8)0.0562 (6)
C21.1882 (2)0.6361 (3)0.08669 (8)0.0579 (6)
H21.23570.60230.11160.069*
C31.0639 (2)0.6078 (3)0.09596 (7)0.0526 (6)
C40.9889 (2)0.6635 (2)0.05837 (7)0.0454 (5)
C50.8588 (2)0.6460 (3)0.06280 (8)0.0546 (6)
H50.81450.59480.09250.066*
C60.7934 (2)0.7013 (3)0.02513 (8)0.0541 (6)
H60.70660.68720.02930.065*
C70.8583 (2)0.7787 (3)0.01941 (8)0.0475 (5)
C80.9869 (2)0.7992 (3)0.02532 (7)0.0470 (5)
H81.03070.85030.05510.056*
C91.0498 (2)0.7438 (2)0.01305 (7)0.0443 (5)
C101.0030 (3)0.5162 (3)0.14454 (8)0.0743 (8)
H10A0.93700.59040.16210.111*
H10B0.96850.40380.13610.111*
H10C1.06480.49590.16630.111*
C110.6738 (2)0.8042 (3)0.05988 (8)0.0569 (6)
H11A0.65240.68100.05090.068*
H11B0.62190.88230.03590.068*
C120.6566 (2)0.8438 (3)0.11425 (8)0.0611 (6)
H12A0.71900.77750.13750.073*
H12B0.67180.97000.12100.073*
C130.5342 (2)0.8006 (3)0.18101 (8)0.0580 (6)
H13A0.56200.91720.19440.070*
H13B0.59450.71280.19690.070*
C140.4084 (2)0.7606 (3)0.19534 (8)0.0572 (6)
H14A0.38320.64030.18440.069*
H14B0.41450.76620.23240.069*
C150.3096 (2)0.8845 (3)0.11589 (7)0.0570 (6)
H15A0.24870.97190.10010.068*
H15B0.28230.76770.10260.068*
C160.4362 (2)0.9263 (3)0.10182 (8)0.0580 (6)
H16A0.43040.92260.06480.070*
H16B0.46121.04610.11330.070*
C170.19665 (19)0.8838 (2)0.18936 (7)0.0421 (5)
C180.1749 (2)0.7849 (3)0.23161 (7)0.0508 (5)
H180.23870.71190.24830.061*
C190.0613 (2)0.7915 (3)0.24977 (7)0.0517 (6)
H190.05060.72500.27850.062*
C200.0357 (2)0.8961 (3)0.22545 (7)0.0485 (5)
C210.0158 (2)0.9946 (3)0.18305 (8)0.0524 (6)
H210.08041.06530.16600.063*
C220.0970 (2)0.9897 (3)0.16589 (7)0.0499 (5)
H220.10781.05900.13770.060*
C230.1775 (2)0.8104 (4)0.28198 (9)0.0760 (8)
H23A0.25930.84060.28930.114*
H23B0.11530.83500.31160.114*
H23C0.17530.68570.27360.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0525 (11)0.0517 (11)0.0468 (10)0.0007 (9)0.0067 (8)0.0028 (8)
N20.0516 (11)0.0458 (10)0.0379 (9)0.0043 (8)0.0028 (8)0.0063 (7)
O10.0602 (10)0.0522 (9)0.0457 (8)0.0058 (7)0.0123 (7)0.0056 (7)
O20.0662 (12)0.0896 (14)0.0756 (11)0.0065 (10)0.0226 (9)0.0157 (9)
O30.0566 (10)0.0688 (11)0.0625 (9)0.0072 (8)0.0163 (8)0.0108 (8)
O40.0641 (11)0.0767 (12)0.0598 (9)0.0069 (9)0.0180 (8)0.0089 (8)
O50.0984 (14)0.0706 (12)0.0981 (13)0.0173 (10)0.0296 (11)0.0117 (10)
C10.0703 (17)0.0490 (14)0.0525 (13)0.0014 (12)0.0197 (13)0.0026 (11)
C20.0834 (18)0.0475 (14)0.0467 (13)0.0015 (12)0.0223 (12)0.0002 (10)
C30.0856 (18)0.0316 (12)0.0414 (11)0.0044 (11)0.0125 (12)0.0024 (9)
C40.0672 (15)0.0296 (11)0.0384 (11)0.0055 (10)0.0056 (10)0.0040 (9)
C50.0731 (17)0.0442 (13)0.0429 (12)0.0119 (11)0.0019 (11)0.0014 (10)
C60.0559 (14)0.0512 (14)0.0535 (13)0.0068 (11)0.0035 (11)0.0080 (11)
C70.0588 (15)0.0368 (12)0.0471 (12)0.0017 (10)0.0091 (11)0.0041 (9)
C80.0569 (14)0.0434 (13)0.0399 (11)0.0034 (10)0.0054 (10)0.0015 (9)
C90.0547 (14)0.0322 (11)0.0451 (11)0.0045 (9)0.0058 (10)0.0061 (9)
C100.110 (2)0.0630 (16)0.0500 (13)0.0117 (15)0.0134 (14)0.0141 (12)
C110.0513 (14)0.0566 (14)0.0628 (14)0.0044 (11)0.0090 (11)0.0024 (11)
C120.0591 (15)0.0631 (16)0.0614 (14)0.0040 (12)0.0111 (12)0.0027 (12)
C130.0578 (15)0.0645 (15)0.0488 (12)0.0065 (12)0.0001 (11)0.0042 (11)
C140.0591 (14)0.0654 (15)0.0452 (11)0.0092 (12)0.0033 (11)0.0141 (11)
C150.0580 (14)0.0681 (15)0.0434 (12)0.0072 (12)0.0038 (10)0.0107 (11)
C160.0637 (15)0.0589 (15)0.0519 (13)0.0050 (12)0.0114 (11)0.0132 (11)
C170.0514 (13)0.0349 (11)0.0380 (10)0.0017 (10)0.0013 (10)0.0010 (9)
C180.0602 (14)0.0445 (13)0.0451 (12)0.0035 (11)0.0007 (11)0.0076 (10)
C190.0648 (15)0.0491 (13)0.0410 (11)0.0030 (11)0.0082 (11)0.0064 (10)
C200.0547 (14)0.0456 (13)0.0442 (11)0.0021 (11)0.0054 (11)0.0041 (10)
C210.0592 (15)0.0455 (13)0.0507 (12)0.0092 (11)0.0035 (11)0.0043 (10)
C220.0630 (15)0.0429 (12)0.0428 (11)0.0038 (11)0.0055 (11)0.0075 (10)
C230.0715 (17)0.096 (2)0.0632 (15)0.0050 (15)0.0203 (13)0.0125 (14)
Geometric parameters (Å, º) top
N1—C161.465 (3)C10—H10B0.9600
N1—C121.461 (3)C10—H10C0.9600
N1—C131.467 (3)C11—C121.505 (3)
N2—C171.414 (3)C11—H11A0.9700
N2—C141.452 (2)C11—H11B0.9700
N2—C151.466 (3)C12—H12A0.9700
O1—C11.375 (3)C12—H12B0.9700
O1—C91.380 (3)C13—C141.496 (3)
O2—C11.210 (3)C13—H13A0.9700
O3—C71.360 (2)C13—H13B0.9700
O3—C111.428 (3)C14—H14A0.9700
O4—C201.373 (2)C14—H14B0.9700
O4—C231.416 (3)C15—C161.505 (3)
O5—H5A0.8786C15—H15A0.9700
O5—H5B0.8689C15—H15B0.9700
C1—C21.436 (3)C16—H16A0.9700
C2—C31.338 (3)C16—H16B0.9700
C2—H20.9300C17—C181.389 (3)
C3—C41.440 (3)C17—C221.395 (3)
C3—C101.506 (3)C18—C191.386 (3)
C4—C51.394 (3)C18—H180.9300
C4—C91.401 (3)C19—C201.377 (3)
C5—C61.373 (3)C19—H190.9300
C5—H50.9300C20—C211.385 (3)
C6—C71.391 (3)C21—C221.365 (3)
C6—H60.9300C21—H210.9300
C7—C81.378 (3)C22—H220.9300
C8—C91.371 (3)C23—H23A0.9600
C8—H80.9300C23—H23B0.9600
C10—H10A0.9600C23—H23C0.9600
C16—N1—C12111.81 (17)N1—C12—H12B108.8
C16—N1—C13108.22 (17)C11—C12—H12B108.8
C12—N1—C13109.31 (16)H12A—C12—H12B107.7
C17—N2—C14116.81 (15)N1—C13—C14112.53 (17)
C17—N2—C15116.63 (16)N1—C13—H13A109.1
C14—N2—C15109.19 (16)C14—C13—H13A109.1
C1—O1—C9121.91 (17)N1—C13—H13B109.1
C7—O3—C11119.84 (17)C14—C13—H13B109.1
C20—O4—C23118.00 (17)H13A—C13—H13B107.8
H5A—O5—H5B99.9N2—C14—C13111.34 (17)
O2—C1—O1116.6 (2)N2—C14—H14A109.4
O2—C1—C2126.5 (2)C13—C14—H14A109.4
O1—C1—C2116.9 (2)N2—C14—H14B109.4
C3—C2—C1123.1 (2)C13—C14—H14B109.4
C3—C2—H2118.5H14A—C14—H14B108.0
C1—C2—H2118.5N2—C15—C16111.45 (17)
C2—C3—C4119.1 (2)N2—C15—H15A109.3
C2—C3—C10120.8 (2)C16—C15—H15A109.3
C4—C3—C10120.1 (2)N2—C15—H15B109.3
C5—C4—C9115.84 (19)C16—C15—H15B109.3
C5—C4—C3125.8 (2)H15A—C15—H15B108.0
C9—C4—C3118.3 (2)N1—C16—C15111.33 (17)
C6—C5—C4122.6 (2)N1—C16—H16A109.4
C6—C5—H5118.7C15—C16—H16A109.4
C4—C5—H5118.7N1—C16—H16B109.4
C5—C6—C7119.4 (2)C15—C16—H16B109.4
C5—C6—H6120.3H16A—C16—H16B108.0
C7—C6—H6120.3C18—C17—C22116.11 (19)
O3—C7—C8115.28 (18)C18—C17—N2123.24 (18)
O3—C7—C6124.8 (2)C22—C17—N2120.59 (17)
C8—C7—C6119.9 (2)C19—C18—C17122.16 (19)
C9—C8—C7119.50 (19)C19—C18—H18118.9
C9—C8—H8120.2C17—C18—H18118.9
C7—C8—H8120.2C20—C19—C18120.34 (19)
C8—C9—O1116.58 (18)C20—C19—H19119.8
C8—C9—C4122.7 (2)C18—C19—H19119.8
O1—C9—C4120.70 (19)O4—C20—C19125.57 (19)
C3—C10—H10A109.5O4—C20—C21116.21 (19)
C3—C10—H10B109.5C19—C20—C21118.2 (2)
H10A—C10—H10B109.5C22—C21—C20121.1 (2)
C3—C10—H10C109.5C22—C21—H21119.4
H10A—C10—H10C109.5C20—C21—H21119.4
H10B—C10—H10C109.5C21—C22—C17122.04 (19)
O3—C11—C12104.33 (17)C21—C22—H22119.0
O3—C11—H11A110.9C17—C22—H22119.0
C12—C11—H11A110.9O4—C23—H23A109.5
O3—C11—H11B110.9O4—C23—H23B109.5
C12—C11—H11B110.9H23A—C23—H23B109.5
H11A—C11—H11B108.9O4—C23—H23C109.5
N1—C12—C11113.87 (18)H23A—C23—H23C109.5
N1—C12—H12A108.8H23B—C23—H23C109.5
C11—C12—H12A108.8
C9—O1—C1—O2179.06 (19)C13—N1—C12—C11166.38 (19)
C9—O1—C1—C21.1 (3)O3—C11—C12—N1173.07 (17)
O2—C1—C2—C3178.4 (2)C16—N1—C13—C1456.4 (2)
O1—C1—C2—C31.7 (3)C12—N1—C13—C14178.35 (18)
C1—C2—C3—C41.5 (3)C17—N2—C14—C13168.91 (17)
C1—C2—C3—C10177.4 (2)C15—N2—C14—C1356.0 (2)
C2—C3—C4—C5178.9 (2)N1—C13—C14—N257.7 (2)
C10—C3—C4—C52.1 (3)C17—N2—C15—C16168.08 (17)
C2—C3—C4—C90.7 (3)C14—N2—C15—C1656.8 (2)
C10—C3—C4—C9178.23 (19)C12—N1—C16—C15176.75 (17)
C9—C4—C5—C60.8 (3)C13—N1—C16—C1556.3 (2)
C3—C4—C5—C6179.57 (19)N2—C15—C16—N158.4 (2)
C4—C5—C6—C70.2 (3)C14—N2—C17—C188.4 (3)
C11—O3—C7—C8173.17 (18)C15—N2—C17—C18140.1 (2)
C11—O3—C7—C66.2 (3)C14—N2—C17—C22174.68 (18)
C5—C6—C7—O3179.25 (19)C15—N2—C17—C2243.0 (3)
C5—C6—C7—C80.0 (3)C22—C17—C18—C190.5 (3)
O3—C7—C8—C9179.71 (18)N2—C17—C18—C19176.64 (18)
C6—C7—C8—C90.3 (3)C17—C18—C19—C201.1 (3)
C7—C8—C9—O1179.68 (17)C23—O4—C20—C192.7 (3)
C7—C8—C9—C41.0 (3)C23—O4—C20—C21177.91 (19)
C1—O1—C9—C8178.94 (18)C18—C19—C20—O4179.94 (19)
C1—O1—C9—C40.4 (3)C18—C19—C20—C210.6 (3)
C5—C4—C9—C81.2 (3)O4—C20—C21—C22178.93 (18)
C3—C4—C9—C8179.13 (18)C19—C20—C21—C220.5 (3)
C5—C4—C9—O1179.52 (17)C20—C21—C22—C171.1 (3)
C3—C4—C9—O10.2 (3)C18—C17—C22—C210.6 (3)
C7—O3—C11—C12166.23 (18)N2—C17—C22—C21177.82 (18)
C16—N1—C12—C1173.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···N10.882.082.955 (3)172
O5—H5B···O2i0.872.192.989 (3)152
C6—H6···O5ii0.932.613.369 (3)139
C23—H23B···O5iii0.962.633.579 (4)170
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z; (iii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H26N2O4·H2O
Mr412.47
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.776 (7), 7.483 (5), 26.381 (18)
β (°) 99.406 (10)
V3)2099 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.53 × 0.48 × 0.27
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.962, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
10516, 3684, 2296
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.124, 1.03
No. of reflections3684
No. of parameters273
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.22

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL and WinGX (Version 1.7; Farrugia, 1999).

Selected geometric parameters (Å, º) top
N1—C161.465 (3)N2—C141.452 (2)
N1—C121.461 (3)N2—C151.466 (3)
N1—C131.467 (3)C13—C141.496 (3)
N2—C171.414 (3)C15—C161.505 (3)
C16—N1—C12111.81 (17)C14—N2—C15109.19 (16)
C16—N1—C13108.22 (17)N1—C13—C14112.53 (17)
C12—N1—C13109.31 (16)N2—C14—C13111.34 (17)
C17—N2—C14116.81 (15)N2—C15—C16111.45 (17)
C17—N2—C15116.63 (16)N1—C16—C15111.33 (17)
N1—C13—C14—N257.7 (2)C23—O4—C20—C192.7 (3)
N2—C15—C16—N158.4 (2)C23—O4—C20—C21177.91 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···N10.882.082.955 (3)172
O5—H5B···O2i0.872.192.989 (3)152
C6—H6···O5ii0.932.613.369 (3)139
C23—H23B···O5iii0.962.633.579 (4)170
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z; (iii) x+1/2, y+1/2, z+1/2.
 

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