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The crystal structures of three angiotensin-II receptor antagonists involving different spacer groups (CO, CONH and NHCO) between the aryl rings are presented, namely 2-{4-[(3-butyl-1,4-dioxo-2,3-di­aza­spiro­[4.4]­non-2-yl)­methyl]­benzoyl}benzoic acid, C26H28N2O5, (I), 2-{4-[(3-butyl-1,4-dioxo-2,3-di­aza­spiro­[4.4]­non-2-yl)­methyl]­benz­amido}benzoic acid, C26H29N3O5, (II), and 2-{4-[(3-butyl-1,4-dioxo-2,3-di­azaspiro­[4.4]­non-2-yl)­methyl]­anilino­carbonyl}benzoic acid monohydrate, C26H29N3O5·H2O, (III). The aryl rings of (II) are almost coplanar, in contrast with compounds (I) and (III). The conformation of (II) is induced by an intramolecular N—H...O hydrogen bond between the amide and carboxyl­ic acid groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101013506/gg1071sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013506/gg1071Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013506/gg1071IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013506/gg1071IIIsup4.hkl
Contains datablock III

CCDC references: 175099; 175100; 175101

Comment top

The renin-angiotensin system (RAS) plays an important role in the regulation of blood pressure and electrolyte balance. Non-peptide AT1-selective angiotensin-II receptor antagonists which block the RAS are of great interest in the treatment of hypertension and other cardiovascular diseases (Wexler et al., 1996). Recently, we reported new pyrazolidine-3,5-dione derivatives displaying AT1-binding affinity (Le Bourdonnec et al., 2000). In this paper, we compare the X-ray structures of three compounds from this series, (I), (II) and (III), involving different spacer groups between the two aryl rings. \sch

The atom-numbering schemes and molecular conformations adopted by the compounds (I), (II) and (III) are depicted in Figs. 1, 2 and 3, respectively. For each compound, the pyrazolidine-3,5-dione heterocycle is almost planar. The displacement of the atoms from their mean plane does not exceed 0.096 Å. The C24 and C6 substituents deviate from that plane by a distance ranging from 0.35 to 0.78 Å. In (III), the terminal part of the butyl chain and the spiropentyl groups are disordered. Two orientations were found for these moieties, with occupancy factors of 0.57 and 0.43 for C26—C27 and C26'-C27', and 0.63 and 0.37 for C29—C30 and C29'-C30'.

The three compounds present some differences in the conformation of the Ph—X-PhCO2Hortho moiety. Indeed, the orientation of the central aryl ring (C7/C8/C9/C10/C11/C12) is quite different for (I) when compared with the other two. The N1—C6—C7—C8 torsion angle is -2.6 (3), -78.4 (3) and -98.4 (2)° for (I), (II) and (III), respectively. Furthermore, the angle between the planes of the two aryl rings varies depending on the nature of the linkage (carbonyl, amide or retroamide). In compound (I), the two rings form a dihedral angle of 82.8 (1)°, with the carbonyl function almost in the same plane as the central aryl ring [C11—C10—C34—O35 - 10.5 (3)°]. In (II), the two phenyl rings are twisted slightly from coplanarity [dihedral angle between the planes 32.3 (1)°], whereas in (III), they are distorted by 88.0 (1)°. In fact, for these two latter derivatives, the amide function is in the same plane as the central aryl ring [the dihedral angle between the planes is 11.5 (5)° for (II) and 10.5 (2)° for (III)].

There is a difference in the orientation of the terminal phenyl ring (C13/C14/C15/C16/C17/C18) with respect to the amide function. In (II), the aryl and amide moieties are almost coplanar [dihedral angle 21.1 (4)°]. This conformation is stabilized by an intramolecular hydrogen bond between the amide and the carboxylic acid moieties (N36—H36···O21; Table 2). In (III), this intramolecular hydrogen bond is not present and the terminal aryl ring is perpendicular to the retroamide group [dihedral angle 81.7 (1)°]. For all three derivatives, the carboxylic acid function is almost coplanar with the corresponding phenyl ring, with torsion angles C13—C14—C19—O21 of 3.7 (3), -12.1 (5) and 4.9 (3)° for (I), (II) and (III), respectively. The C14—C19 distances, ranging from 1.480 to 1.489 Å, are shorter than common single bonds, indicative of a delocalization between the two groups.

In addition to the intramolecular hydrogen bond observed in (II), some intermolecular donor-acceptor interactions are also found for the three derivatives; details of these are given in Tables 1, 2 and 3. For (I) and (II), the carboxylic acid group is involved in a hydrogen bond with the O33 acceptor atom (O20—H20···O33; Tables 1 and 2). For compound (III), the co-crystallized water molecule is involved in the hydrogen-bonding pattern. It interacts as a double H-donor with the pyrazolidine-3,5-dione heterocycle (O37—H37A···O33 and O37—H37B···O32, Table 3) and as an H-acceptor with the carboxylic acid moiety (O20—H20···O37, Table 3). Furthermore, an intermolecular hydrogen bond exists between the amide functions (N36—H36···O35, Table 3).

Related literature top

For related literature, see: Le Bourdonnec, Meulon, Yous, Goossens, Houssin & Hénichart (2000); Sheldrick (1997); Wexler et al. (1996).

Experimental top

The synthesis of compounds (I), (II) and (III) has been reported previously by Le Bourdonnec et al. (2000). Crystals were obtained by slow evaporation of an isooctane-ethyl acetate solution for (I), a toluene-ethyl acetate solution for (II) and an ethyl acetate solution (III), at room temperature.

Refinement top

H atoms attached to C were treated as riding using the SHELXL97 (Sheldrick, 1997) defaults, whereas the N—H and O—H atoms were refined on position and with isotropic displacement parameters.

Computing details top

For all compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: PLATON (Spek, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular view of compound (I), with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The molecular view of compound (II), with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. The molecular view of compound (III), with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii. Only one conformation of the terminal part of the alkyl chain (C26–27) and the spiropentyl group (C29—C30) is shown.
(I) 2-{4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzoyl}benzoic acid top
Crystal data top
C26H28N2O5Z = 2
Mr = 448.50F(000) = 476
Triclinic, P1Dx = 1.295 Mg m3
a = 10.530 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.469 (1) ÅCell parameters from 25 reflections
c = 11.491 (1) Åθ = 40–50°
α = 109.589 (8)°µ = 0.73 mm1
β = 112.690 (8)°T = 293 K
γ = 97.640 (9)°Block, colourless
V = 1150.02 (18) Å30.31 × 0.29 × 0.23 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3537 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 71.9°, θmin = 4.3°
θ/2θ scansh = 1212
Absorption correction: ψ-scan
(North et al., 1968)
k = 014
Tmin = 0.804, Tmax = 0.849l = 1413
4750 measured reflections3 standard reflections every 200 reflections
4511 independent reflections intensity decay: 2%
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0781P)2 + 0.3037P]
where P = (Fo2 + 2Fc2)/3
4511 reflections(Δ/σ)max = 0.002
302 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C26H28N2O5γ = 97.640 (9)°
Mr = 448.50V = 1150.02 (18) Å3
Triclinic, P1Z = 2
a = 10.530 (1) ÅCu Kα radiation
b = 11.469 (1) ŵ = 0.73 mm1
c = 11.491 (1) ÅT = 293 K
α = 109.589 (8)°0.31 × 0.29 × 0.23 mm
β = 112.690 (8)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3537 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(North et al., 1968)
Rint = 0.043
Tmin = 0.804, Tmax = 0.8493 standard reflections every 200 reflections
4750 measured reflections intensity decay: 2%
4511 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.28 e Å3
4511 reflectionsΔρmin = 0.28 e Å3
302 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.

# Data for C—H···O interactions # # For Instance, # # Compound (I): # C(6)—H(6 A)···O(21)i D—A= 3.0209 D—H···A=124.48 (i=2 - x,-y,2 - z) # C(9)—H(9)···O(32)ii D—A=3.1716 D—H···A=131.04 (ii=1 - x,-y,1 - z) # C(12)—H(12)···O(21)i D—A=3.2667 D—H···A=135.52 (i=2 - x,-y,2 - z) # C(28)—H(28B)···O(32)ii D—A=3.3832 D—H···A=143.77 (ii=1 - x,-y,1 - z) # # Compound (II): # C(12)—H(12)···O(35)i D—A=3.1459 D—H···A=125.89 (i=1 - x,1/2 + y,1/2 - z) # # But I have decided not to focus on the C—H···O interactions in this paper, # the main aim being to compare the relative orientation of the aromatic rings # depending on the spacer group used. #

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
N10.72722 (16)0.26599 (15)0.84015 (15)0.0503 (4)
N20.59599 (16)0.16468 (15)0.77948 (15)0.0507 (4)
O200.83499 (18)0.50818 (15)0.58895 (17)0.0691 (4)
O210.9737 (2)0.31438 (15)0.75704 (15)0.0806 (5)
O320.37165 (16)0.10416 (15)0.59768 (16)0.0702 (4)
O330.82428 (18)0.41119 (16)0.78013 (17)0.0710 (4)
O351.22986 (17)0.12416 (17)0.78133 (18)0.0868 (6)
C30.4987 (2)0.16936 (18)0.66293 (19)0.0528 (4)
C40.5753 (2)0.26530 (18)0.63038 (19)0.0518 (4)
C50.7218 (2)0.32541 (18)0.7557 (2)0.0523 (4)
C60.8609 (2)0.2599 (2)0.93987 (19)0.0552 (5)
C70.91829 (19)0.15374 (17)0.87804 (18)0.0458 (4)
C80.8476 (2)0.06586 (18)0.73994 (19)0.0520 (4)
C90.90627 (19)0.02782 (18)0.68734 (19)0.0499 (4)
C101.03793 (18)0.03457 (17)0.77244 (19)0.0476 (4)
C111.1093 (2)0.05371 (19)0.91154 (19)0.0542 (5)
C121.0504 (2)0.14596 (19)0.96411 (19)0.0529 (4)
C131.01546 (19)0.23084 (18)0.56600 (19)0.0502 (4)
C140.92682 (19)0.35290 (18)0.52749 (18)0.0481 (4)
C150.8484 (2)0.4396 (2)0.3873 (2)0.0574 (5)
C160.8570 (2)0.4038 (2)0.2868 (2)0.0664 (6)
C170.9430 (3)0.2832 (3)0.3244 (2)0.0685 (6)
C181.0232 (2)0.1975 (2)0.4630 (2)0.0626 (5)
C190.9153 (2)0.38852 (18)0.6366 (2)0.0519 (4)
C240.5589 (2)0.1155 (2)0.8676 (2)0.0597 (5)
C250.5446 (3)0.2153 (2)0.9840 (2)0.0683 (6)
C260.4273 (3)0.2748 (3)0.9363 (3)0.0742 (6)
C270.4133 (4)0.3697 (3)1.0567 (3)0.0941 (8)
C280.5888 (3)0.1963 (2)0.4951 (2)0.0684 (6)
C290.4990 (4)0.2386 (4)0.3918 (3)0.1090 (12)
C300.4234 (4)0.3179 (3)0.4467 (3)0.1056 (11)
C310.4922 (3)0.3618 (2)0.6003 (2)0.0683 (6)
C341.1048 (2)0.13075 (19)0.7155 (2)0.0546 (5)
H6A0.84450.24691.01270.066*
H6B0.93420.34290.98280.066*
H80.75940.06940.68120.062*
H90.85670.08650.59410.060*
H111.19790.05060.97000.065*
H121.09920.20351.05780.063*
H150.79040.52140.36160.069*
H160.80450.46140.19330.080*
H170.94730.25910.25610.082*
H181.08290.11680.48740.075*
H200.838 (3)0.535 (3)0.655 (3)0.104 (10)*
H24A0.63230.07830.90830.072*
H24B0.46820.04610.80940.072*
H25A0.52650.17441.03980.082*
H25B0.63580.28401.04340.082*
H26A0.33620.20650.87400.089*
H26B0.44730.31990.88440.089*
H27A0.33710.40521.02130.141*
H27B0.50260.43851.11760.141*
H27C0.39150.32511.10720.141*
H28A0.68860.22100.51320.082*
H28B0.55460.10280.46120.082*
H29A0.55990.28740.36810.131*
H29B0.43020.16310.30760.131*
H30A0.32280.26860.40560.127*
H30B0.42770.39250.42470.127*
H31A0.41940.36070.63240.082*
H31B0.55780.44930.64700.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0506 (8)0.0512 (8)0.0451 (8)0.0209 (7)0.0158 (7)0.0211 (7)
N20.0503 (8)0.0521 (8)0.0463 (8)0.0201 (7)0.0161 (7)0.0226 (7)
O200.0770 (10)0.0649 (9)0.0631 (9)0.0124 (8)0.0300 (8)0.0307 (8)
O210.1244 (14)0.0620 (9)0.0471 (8)0.0262 (9)0.0316 (9)0.0238 (7)
O320.0561 (8)0.0680 (9)0.0635 (9)0.0178 (7)0.0078 (7)0.0254 (7)
O330.0750 (10)0.0686 (9)0.0710 (10)0.0164 (8)0.0322 (8)0.0348 (8)
O350.0555 (9)0.0882 (12)0.0794 (11)0.0383 (8)0.0086 (8)0.0137 (9)
C30.0573 (11)0.0500 (10)0.0447 (9)0.0269 (8)0.0153 (8)0.0183 (8)
C40.0649 (11)0.0498 (10)0.0444 (9)0.0319 (9)0.0222 (8)0.0221 (8)
C50.0616 (11)0.0496 (10)0.0504 (10)0.0263 (9)0.0273 (9)0.0213 (8)
C60.0508 (10)0.0615 (11)0.0422 (9)0.0236 (9)0.0124 (8)0.0176 (8)
C70.0457 (9)0.0482 (9)0.0439 (9)0.0161 (7)0.0183 (7)0.0219 (7)
C80.0451 (9)0.0546 (10)0.0464 (9)0.0206 (8)0.0113 (8)0.0196 (8)
C90.0460 (9)0.0465 (9)0.0450 (9)0.0153 (7)0.0119 (7)0.0161 (7)
C100.0425 (9)0.0465 (9)0.0504 (10)0.0138 (7)0.0160 (7)0.0230 (8)
C110.0440 (9)0.0609 (11)0.0479 (10)0.0199 (8)0.0106 (8)0.0232 (9)
C120.0495 (10)0.0594 (11)0.0400 (9)0.0179 (8)0.0126 (8)0.0187 (8)
C130.0467 (9)0.0548 (10)0.0534 (10)0.0258 (8)0.0224 (8)0.0246 (8)
C140.0473 (9)0.0543 (10)0.0471 (9)0.0254 (8)0.0219 (8)0.0225 (8)
C150.0569 (11)0.0590 (11)0.0507 (10)0.0207 (9)0.0226 (9)0.0186 (9)
C160.0687 (13)0.0788 (15)0.0477 (11)0.0253 (11)0.0256 (10)0.0227 (10)
C170.0735 (14)0.0885 (16)0.0623 (13)0.0341 (12)0.0381 (11)0.0413 (12)
C180.0629 (12)0.0660 (12)0.0709 (13)0.0251 (10)0.0347 (11)0.0358 (11)
C190.0561 (10)0.0530 (10)0.0500 (10)0.0264 (9)0.0227 (8)0.0237 (8)
C240.0661 (12)0.0593 (11)0.0609 (12)0.0255 (10)0.0261 (10)0.0347 (10)
C250.0725 (14)0.0792 (15)0.0583 (12)0.0245 (12)0.0308 (11)0.0335 (11)
C260.0803 (15)0.0774 (15)0.0661 (13)0.0305 (12)0.0356 (12)0.0269 (12)
C270.103 (2)0.0919 (19)0.0842 (18)0.0361 (16)0.0506 (16)0.0217 (15)
C280.0931 (16)0.0683 (13)0.0513 (11)0.0424 (12)0.0353 (11)0.0245 (10)
C290.108 (2)0.183 (4)0.0621 (15)0.077 (2)0.0406 (16)0.066 (2)
C300.130 (3)0.0799 (17)0.0800 (18)0.0537 (18)0.0079 (17)0.0429 (15)
C310.0822 (15)0.0634 (12)0.0757 (14)0.0467 (11)0.0362 (12)0.0387 (11)
C340.0467 (10)0.0547 (10)0.0576 (11)0.0215 (8)0.0171 (8)0.0241 (9)
Geometric parameters (Å, º) top
N1—N21.426 (2)C11—H110.9300
N1—C51.350 (2)C8—H80.9300
N1—C61.461 (2)C12—H120.9300
N2—C31.360 (2)C18—C171.381 (3)
N2—C241.458 (2)C18—H180.9300
O20—C191.315 (2)C6—H6A0.9700
O21—C191.196 (2)C6—H6B0.9700
O32—C31.223 (2)C4—C311.546 (2)
O33—C51.228 (2)C4—C281.561 (3)
O35—C341.216 (2)C16—C171.372 (3)
O20—H200.90 (3)C16—H160.9300
C3—C41.508 (3)C25—C261.499 (3)
C7—C61.517 (3)C25—H25A0.9700
C7—C81.380 (2)C25—H25B0.9700
C7—C121.397 (2)C17—H170.9300
C9—C81.389 (3)C28—C291.476 (3)
C9—C101.385 (2)C28—H28A0.9700
C9—H90.9300C28—H28B0.9700
C10—C111.389 (3)C31—C301.488 (4)
C10—C341.489 (3)C31—H31A0.9700
C13—C181.387 (3)C31—H31B0.9700
C13—C141.395 (3)C26—C271.519 (3)
C13—C341.516 (3)C26—H26A0.9700
C15—C161.378 (3)C26—H26B0.9700
C15—C141.396 (3)C30—C291.434 (4)
C15—H150.9300C30—H30A0.9700
C19—C141.484 (3)C30—H30B0.9700
C5—C41.505 (3)C27—H27A0.9600
C24—C251.515 (3)C27—H27B0.9600
C24—H24A0.9700C27—H27C0.9600
C24—H24B0.9700C29—H29A0.9700
C11—C121.380 (3)C29—H29B0.9700
C19—O20—H20115 (2)N1—C6—H6B108.6
C3—N2—N1109.28 (15)C7—C6—H6B108.6
C3—N2—C24124.83 (17)H6A—C6—H6B107.6
N1—N2—C24119.48 (15)C5—C4—C3102.61 (15)
C5—N1—N2110.43 (15)C5—C4—C31115.30 (17)
C5—N1—C6123.91 (17)C3—C4—C31112.62 (17)
N2—N1—C6119.93 (15)C5—C4—C28110.62 (17)
C10—C9—C8120.61 (17)C3—C4—C28111.63 (17)
C10—C9—H9119.7C31—C4—C28104.30 (16)
C8—C9—H9119.7C17—C16—C15120.1 (2)
C9—C10—C11118.52 (17)C17—C16—H16120.0
C9—C10—C34120.96 (17)C15—C16—H16120.0
C11—C10—C34120.48 (16)C26—C25—C24114.60 (19)
O32—C3—N2124.11 (19)C26—C25—H25A108.6
O32—C3—C4127.51 (17)C24—C25—H25A108.6
N2—C3—C4108.38 (17)C26—C25—H25B108.6
O21—C19—O20123.28 (19)C24—C25—H25B108.6
O21—C19—C14122.71 (19)H25A—C25—H25B107.6
O20—C19—C14114.01 (17)C16—C17—C18120.5 (2)
C8—C7—C12118.32 (16)C16—C17—H17119.7
C8—C7—C6123.12 (16)C18—C17—H17119.7
C12—C7—C6118.55 (16)C29—C28—C4106.50 (19)
C18—C13—C14118.96 (18)C29—C28—H28A110.4
C18—C13—C34117.38 (18)C4—C28—H28A110.4
C14—C13—C34123.66 (17)C29—C28—H28B110.4
C16—C15—C14120.0 (2)C4—C28—H28B110.4
C16—C15—H15120.0H28A—C28—H28B108.6
C14—C15—H15120.0C30—C31—C4106.15 (18)
O33—C5—N1123.37 (18)C30—C31—H31A110.5
O33—C5—C4128.08 (18)C4—C31—H31A110.5
N1—C5—C4108.52 (17)C30—C31—H31B110.5
C13—C14—C15119.99 (18)C4—C31—H31B110.5
C13—C14—C19119.40 (17)H31A—C31—H31B108.7
C15—C14—C19120.61 (18)C25—C26—C27112.4 (2)
N2—C24—C25115.18 (17)C25—C26—H26A109.1
N2—C24—H24A108.5C27—C26—H26A109.1
C25—C24—H24A108.5C25—C26—H26B109.1
N2—C24—H24B108.5C27—C26—H26B109.1
C25—C24—H24B108.5H26A—C26—H26B107.9
H24A—C24—H24B107.5C29—C30—C31108.6 (2)
C12—C11—C10120.88 (16)C29—C30—H30A110.0
C12—C11—H11119.6C31—C30—H30A110.0
C10—C11—H11119.6C29—C30—H30B110.0
C7—C8—C9121.01 (16)C31—C30—H30B110.0
C7—C8—H8119.5H30A—C30—H30B108.3
C9—C8—H8119.5C26—C27—H27A109.5
O35—C34—C10121.94 (18)C26—C27—H27B109.5
O35—C34—C13120.38 (18)H27A—C27—H27B109.5
C10—C34—C13117.43 (15)C26—C27—H27C109.5
C11—C12—C7120.66 (17)H27A—C27—H27C109.5
C11—C12—H12119.7H27B—C27—H27C109.5
C7—C12—H12119.7C30—C29—C28110.3 (2)
C17—C18—C13120.4 (2)C30—C29—H29A109.6
C17—C18—H18119.8C28—C29—H29A109.6
C13—C18—H18119.8C30—C29—H29B109.6
N1—C6—C7114.67 (15)C28—C29—H29B109.6
N1—C6—H6A108.6H29A—C29—H29B108.1
C7—C6—H6A108.6
C3—N2—N1—C57.5 (2)C18—C13—C34—C1087.8 (2)
C24—N2—N1—C5160.70 (16)C14—C13—C34—C1092.0 (2)
C3—N2—N1—C6161.83 (16)C10—C11—C12—C70.8 (3)
C24—N2—N1—C645.0 (2)C8—C7—C12—C110.8 (3)
C8—C9—C10—C110.5 (3)C6—C7—C12—C11177.88 (18)
C8—C9—C10—C34177.18 (18)C14—C13—C18—C170.8 (3)
N1—N2—C3—O32171.43 (18)C34—C13—C18—C17179.01 (18)
C24—N2—C3—O3220.0 (3)C5—N1—C6—C782.0 (2)
N1—N2—C3—C49.27 (19)N2—N1—C6—C768.7 (2)
C24—N2—C3—C4160.73 (17)C8—C7—C6—N12.6 (3)
N2—N1—C5—O33175.75 (17)C12—C7—C6—N1176.04 (17)
C6—N1—C5—O3322.6 (3)O33—C5—C4—C3179.01 (19)
N2—N1—C5—C42.3 (2)N1—C5—C4—C33.05 (19)
C6—N1—C5—C4155.43 (16)O33—C5—C4—C3156.2 (3)
C18—C13—C14—C150.4 (3)N1—C5—C4—C31125.85 (19)
C34—C13—C14—C15179.81 (17)O33—C5—C4—C2861.8 (3)
C18—C13—C14—C19178.69 (17)N1—C5—C4—C28116.14 (18)
C34—C13—C14—C191.1 (3)O32—C3—C4—C5173.19 (19)
C16—C15—C14—C130.9 (3)N2—C3—C4—C57.54 (19)
C16—C15—C14—C19178.17 (18)O32—C3—C4—C3148.6 (3)
O21—C19—C14—C133.7 (3)N2—C3—C4—C31132.12 (17)
O20—C19—C14—C13176.50 (16)O32—C3—C4—C2868.3 (2)
O21—C19—C14—C15175.4 (2)N2—C3—C4—C28110.94 (18)
O20—C19—C14—C154.4 (3)C14—C15—C16—C170.2 (3)
C3—N2—C24—C2589.1 (2)N2—C24—C25—C2662.3 (3)
N1—N2—C24—C2559.7 (2)C15—C16—C17—C181.0 (3)
C9—C10—C11—C120.2 (3)C13—C18—C17—C161.5 (3)
C34—C10—C11—C12177.82 (18)C5—C4—C28—C29132.7 (2)
C12—C7—C8—C90.2 (3)C3—C4—C28—C29113.8 (2)
C6—C7—C8—C9178.44 (18)C31—C4—C28—C298.1 (3)
C10—C9—C8—C70.4 (3)C5—C4—C31—C30138.9 (2)
C9—C10—C34—O35167.1 (2)C3—C4—C31—C30103.8 (2)
C11—C10—C34—O3510.5 (3)C28—C4—C31—C3017.4 (3)
C9—C10—C34—C137.2 (3)C24—C25—C26—C27177.5 (2)
C11—C10—C34—C13175.19 (18)C4—C31—C30—C2921.0 (4)
C18—C13—C34—O3586.6 (3)C31—C30—C29—C2816.2 (4)
C14—C13—C34—O3593.6 (3)C4—C28—C29—C304.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O33i0.90 (3)1.79 (3)2.687 (3)174 (3)
Symmetry code: (i) x, y1, z.
(II) 2-{4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzamido}benzoic acid top
Crystal data top
C26H29N3O5F(000) = 984
Mr = 463.52Dx = 1.273 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 16.122 (1) ÅCell parameters from 25 reflections
b = 12.682 (1) Åθ = 40–50°
c = 11.920 (1) ŵ = 0.73 mm1
β = 97.139 (7)°T = 293 K
V = 2418.3 (3) Å3Platelet, colourless
Z = 40.29 × 0.10 × 0.03 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 71.9°, θmin = 2.8°
θ/2θ scansh = 1914
Absorption correction: ψ-scan
(North et al., 1968)
k = 150
Tmin = 0.817, Tmax = 0.979l = 1414
6842 measured reflections3 standard reflections every 200 reflections
4757 independent reflections intensity decay: 5%
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0743P)2]
where P = (Fo2 + 2Fc2)/3
4757 reflections(Δ/σ)max = 0.001
315 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C26H29N3O5V = 2418.3 (3) Å3
Mr = 463.52Z = 4
Monoclinic, P21/cCu Kα radiation
a = 16.122 (1) ŵ = 0.73 mm1
b = 12.682 (1) ÅT = 293 K
c = 11.920 (1) Å0.29 × 0.10 × 0.03 mm
β = 97.139 (7)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
1972 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(North et al., 1968)
Rint = 0.026
Tmin = 0.817, Tmax = 0.9793 standard reflections every 200 reflections
6842 measured reflections intensity decay: 5%
4757 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.16 e Å3
4757 reflectionsΔρmin = 0.19 e Å3
315 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
N10.75196 (14)0.31191 (18)0.08483 (19)0.0619 (6)
N20.79968 (16)0.3532 (2)0.1841 (2)0.0711 (7)
N360.42476 (15)0.24051 (19)0.4566 (2)0.0635 (7)
O200.26337 (15)0.4600 (2)0.5723 (2)0.0911 (8)
O210.37228 (15)0.43965 (16)0.47795 (18)0.0873 (7)
O320.92380 (16)0.3099 (2)0.2859 (2)0.1234 (10)
O330.74249 (13)0.15749 (16)0.00985 (18)0.0826 (6)
O350.44966 (17)0.07812 (17)0.39129 (19)0.1074 (9)
C30.8656 (2)0.2876 (3)0.2159 (3)0.0824 (9)
C40.85237 (18)0.1871 (2)0.1481 (3)0.0717 (8)
C50.77823 (18)0.2137 (2)0.0653 (3)0.0637 (8)
C60.66386 (17)0.3412 (2)0.0633 (2)0.0673 (8)
C70.61228 (16)0.2987 (2)0.1503 (2)0.0604 (7)
C80.58653 (17)0.1939 (2)0.1468 (2)0.0658 (8)
C90.53781 (17)0.1562 (2)0.2241 (2)0.0647 (8)
C100.51285 (17)0.2207 (2)0.3085 (2)0.0573 (7)
C110.54011 (17)0.3241 (2)0.3132 (2)0.0643 (8)
C120.58881 (17)0.3625 (2)0.2349 (2)0.0640 (8)
C130.37666 (17)0.2158 (2)0.5437 (2)0.0558 (7)
C140.32692 (17)0.2943 (2)0.5838 (2)0.0575 (7)
C150.28030 (18)0.2703 (2)0.6713 (2)0.0702 (8)
C160.2830 (2)0.1721 (3)0.7187 (3)0.0791 (9)
C170.3327 (2)0.0958 (2)0.6800 (3)0.0766 (9)
C180.37901 (18)0.1157 (2)0.5927 (2)0.0656 (8)
C190.3244 (2)0.4031 (2)0.5385 (3)0.0655 (8)
C240.8091 (2)0.4681 (2)0.1897 (3)0.0834 (10)
C250.8529 (2)0.5140 (3)0.0956 (3)0.0857 (10)
C260.8598 (2)0.6339 (3)0.1031 (3)0.1074 (12)
C270.9102 (3)0.6808 (3)0.0196 (3)0.1346 (16)
C280.8321 (3)0.0929 (3)0.2237 (3)0.1151 (13)
C290.9029 (4)0.0215 (4)0.2255 (6)0.196 (3)
C300.9439 (4)0.0389 (5)0.1296 (5)0.178 (2)
C310.9306 (2)0.1511 (3)0.0975 (3)0.1104 (13)
C340.45959 (18)0.1732 (2)0.3879 (2)0.0650 (8)
H6A0.64100.31520.01070.081*
H6B0.65950.41750.06180.081*
H80.60260.14920.09160.079*
H90.52100.08600.22020.078*
H110.52550.36840.36970.077*
H120.60610.43250.23930.077*
H150.24670.32200.69790.084*
H160.25140.15710.77690.095*
H170.33510.02940.71320.092*
H180.41170.06270.56660.079*
H200.264 (2)0.520 (3)0.545 (3)0.116 (15)*
H24A0.84040.48680.26180.100*
H24B0.75410.49990.18680.100*
H25A0.82230.49480.02330.103*
H25B0.90850.48400.09940.103*
H26A0.80400.66380.09160.129*
H26B0.88470.65300.17860.129*
H27A0.91070.75610.02740.202*
H27B0.88610.66210.05540.202*
H27C0.96640.65450.03300.202*
H28A0.82590.11680.29950.138*
H28B0.78090.05830.19200.138*
H29A0.94150.03310.29350.235*
H29B0.88360.05090.22600.235*
H30A0.92100.00660.06800.213*
H30B1.00320.02420.14690.213*
H31A0.92240.15860.01590.133*
H31B0.97850.19320.12750.133*
H360.4257 (19)0.315 (3)0.447 (2)0.098 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0600 (15)0.0527 (15)0.0715 (16)0.0045 (12)0.0024 (12)0.0094 (12)
N20.0702 (17)0.0648 (17)0.0766 (17)0.0085 (14)0.0030 (14)0.0116 (13)
N360.0752 (16)0.0428 (15)0.0737 (17)0.0023 (12)0.0137 (14)0.0032 (13)
O200.1063 (18)0.0576 (15)0.1172 (19)0.0203 (14)0.0445 (15)0.0195 (14)
O210.1162 (18)0.0525 (13)0.1016 (17)0.0067 (12)0.0470 (16)0.0109 (11)
O320.1002 (19)0.140 (2)0.117 (2)0.0145 (17)0.0389 (17)0.0007 (17)
O330.0890 (15)0.0594 (13)0.0989 (16)0.0102 (11)0.0098 (13)0.0181 (12)
O350.172 (2)0.0478 (14)0.1143 (19)0.0136 (14)0.0631 (17)0.0133 (12)
C30.070 (2)0.092 (3)0.082 (2)0.010 (2)0.0011 (19)0.008 (2)
C40.0616 (19)0.068 (2)0.086 (2)0.0016 (16)0.0122 (17)0.0152 (18)
C50.0654 (19)0.0530 (19)0.074 (2)0.0086 (16)0.0128 (17)0.0006 (16)
C60.0634 (19)0.0598 (19)0.076 (2)0.0039 (15)0.0006 (16)0.0027 (15)
C70.0534 (16)0.0555 (18)0.0702 (19)0.0058 (14)0.0003 (15)0.0031 (16)
C80.0644 (18)0.059 (2)0.074 (2)0.0008 (15)0.0100 (16)0.0069 (15)
C90.0698 (19)0.0443 (17)0.079 (2)0.0005 (14)0.0042 (17)0.0052 (15)
C100.0621 (17)0.0433 (17)0.0640 (17)0.0066 (14)0.0016 (14)0.0003 (14)
C110.0706 (19)0.0465 (18)0.075 (2)0.0063 (15)0.0075 (17)0.0023 (14)
C120.0643 (19)0.0462 (17)0.080 (2)0.0015 (14)0.0015 (17)0.0001 (16)
C130.0567 (16)0.0472 (17)0.0615 (18)0.0050 (14)0.0004 (14)0.0024 (14)
C140.0660 (18)0.0440 (17)0.0612 (17)0.0019 (14)0.0035 (15)0.0006 (14)
C150.077 (2)0.059 (2)0.076 (2)0.0031 (16)0.0146 (18)0.0026 (16)
C160.090 (2)0.065 (2)0.085 (2)0.0014 (19)0.0197 (19)0.0168 (18)
C170.089 (2)0.0531 (19)0.088 (2)0.0036 (18)0.010 (2)0.0160 (17)
C180.074 (2)0.0490 (18)0.072 (2)0.0017 (15)0.0019 (17)0.0033 (15)
C190.076 (2)0.0513 (19)0.069 (2)0.0047 (17)0.0119 (17)0.0026 (15)
C240.088 (2)0.069 (2)0.092 (2)0.0104 (18)0.008 (2)0.0254 (18)
C250.084 (2)0.074 (2)0.099 (2)0.0143 (18)0.013 (2)0.0085 (19)
C260.102 (3)0.081 (3)0.139 (3)0.016 (2)0.012 (3)0.003 (2)
C270.129 (3)0.117 (4)0.159 (4)0.033 (3)0.023 (3)0.029 (3)
C280.134 (3)0.096 (3)0.115 (3)0.015 (3)0.014 (3)0.042 (2)
C290.147 (5)0.120 (5)0.309 (9)0.018 (4)0.016 (5)0.100 (5)
C300.174 (6)0.130 (5)0.229 (7)0.078 (4)0.027 (5)0.023 (4)
C310.079 (2)0.129 (4)0.126 (3)0.011 (2)0.024 (2)0.016 (3)
C340.079 (2)0.0463 (19)0.068 (2)0.0000 (16)0.0047 (17)0.0036 (15)
Geometric parameters (Å, º) top
N1—N21.429 (3)C17—H170.9300
N1—C51.345 (3)C18—H180.9300
N1—C61.460 (3)C12—H120.9300
N2—C31.366 (4)C15—H150.9300
N2—C241.466 (4)C4—C31.510 (4)
N36—C131.407 (3)C4—C311.533 (4)
N36—C341.352 (3)C4—C281.555 (4)
N36—H360.95 (3)C6—H6A0.9700
O20—C191.322 (3)C6—H6B0.9700
O21—C191.213 (3)C24—C251.514 (4)
O20—H200.83 (4)C24—H24A0.9700
O32—C31.209 (3)C24—H24B0.9700
O33—C51.231 (3)C25—C261.525 (4)
O35—C341.218 (3)C25—H25A0.9700
C8—C91.369 (4)C25—H25B0.9700
C8—C71.392 (4)C28—C291.455 (6)
C8—H80.9300C28—H28A0.9700
C10—C111.382 (4)C28—H28B0.9700
C10—C91.394 (3)C31—C301.482 (6)
C11—C121.380 (3)C31—H31A0.9700
C11—H110.9300C31—H31B0.9700
C14—C151.393 (4)C26—C271.486 (4)
C14—C131.399 (4)C26—H26A0.9700
C14—C191.480 (4)C26—H26B0.9700
C5—C41.491 (4)C27—H27A0.9600
C9—H90.9300C27—H27B0.9600
C13—C181.396 (4)C27—H27C0.9600
C7—C121.382 (3)C29—C301.408 (6)
C7—C61.507 (4)C34—C101.482 (4)
C16—C151.366 (4)C29—H29A0.9700
C16—C171.372 (4)C29—H29B0.9700
C16—H160.9300C30—H30A0.9700
C17—C181.377 (4)C30—H30B0.9700
C19—O20—H20110 (2)C3—C4—C28111.4 (3)
C5—N1—N2109.5 (2)C31—C4—C28104.0 (3)
C5—N1—C6121.7 (2)N1—C6—C7113.3 (2)
N2—N1—C6117.7 (2)N1—C6—H6A108.9
C34—N36—C13128.0 (3)C7—C6—H6A108.9
C34—N36—H36122.4 (18)N1—C6—H6B108.9
C13—N36—H36109.4 (18)C7—C6—H6B108.9
C3—N2—N1109.1 (2)H6A—C6—H6B107.7
C3—N2—C24121.4 (3)O32—C3—N2124.0 (3)
N1—N2—C24116.3 (2)O32—C3—C4127.8 (3)
O35—C34—N36122.6 (3)N2—C3—C4108.2 (3)
O35—C34—C10120.8 (3)N2—C24—C25113.8 (3)
N36—C34—C10116.6 (3)N2—C24—H24A108.8
C15—C14—C13119.1 (3)C25—C24—H24A108.8
C15—C14—C19118.9 (3)N2—C24—H24B108.8
C13—C14—C19122.0 (3)C25—C24—H24B108.8
C11—C10—C9117.8 (3)H24A—C24—H24B107.7
C11—C10—C34124.5 (3)C24—C25—C26112.1 (3)
C9—C10—C34117.7 (3)C24—C25—H25A109.2
C9—C8—C7120.5 (3)C26—C25—H25A109.2
C9—C8—H8119.7C24—C25—H25B109.2
C7—C8—H8119.7C26—C25—H25B109.2
C12—C11—C10120.8 (3)H25A—C25—H25B107.9
C12—C11—H11119.6C29—C28—C4105.4 (3)
C10—C11—H11119.6C29—C28—H28A110.7
O33—C5—N1122.2 (3)C4—C28—H28A110.7
O33—C5—C4127.9 (3)C29—C28—H28B110.7
N1—C5—C4109.8 (3)C4—C28—H28B110.7
C8—C9—C10121.5 (3)H28A—C28—H28B108.8
C8—C9—H9119.3C30—C31—C4106.5 (3)
C10—C9—H9119.3C30—C31—H31A110.4
C18—C13—C14119.4 (3)C4—C31—H31A110.4
C18—C13—N36121.5 (3)C30—C31—H31B110.4
C14—C13—N36119.0 (2)C4—C31—H31B110.4
C12—C7—C8118.2 (3)H31A—C31—H31B108.6
C12—C7—C6121.2 (3)C27—C26—C25113.7 (3)
C8—C7—C6120.6 (3)C27—C26—H26A108.8
C15—C16—C17119.6 (3)C25—C26—H26A108.8
C15—C16—H16120.2C27—C26—H26B108.8
C17—C16—H16120.2C25—C26—H26B108.8
C16—C17—C18121.3 (3)H26A—C26—H26B107.7
C16—C17—H17119.4C26—C27—H27A109.5
C18—C17—H17119.4C26—C27—H27B109.5
C17—C18—C13119.6 (3)H27A—C27—H27B109.5
C17—C18—H18120.2C26—C27—H27C109.5
C13—C18—H18120.2H27A—C27—H27C109.5
C11—C12—C7121.2 (3)H27B—C27—H27C109.5
C11—C12—H12119.4C30—C29—C28109.7 (5)
C7—C12—H12119.4C30—C29—H29A109.7
C16—C15—C14121.1 (3)C28—C29—H29A109.7
C16—C15—H15119.4C30—C29—H29B109.7
C14—C15—H15119.4C28—C29—H29B109.7
O21—C19—O20121.7 (3)H29A—C29—H29B108.2
O21—C19—C14125.6 (3)C29—C30—C31107.0 (5)
O20—C19—C14112.7 (3)C29—C30—H30A110.3
C5—C4—C3102.2 (3)C31—C30—H30A110.3
C5—C4—C31116.0 (3)C29—C30—H30B110.3
C3—C4—C31113.1 (3)C31—C30—H30B110.3
C5—C4—C28110.4 (3)H30A—C30—H30B108.6
C5—N1—N2—C310.4 (3)C15—C14—C19—O21166.0 (3)
C6—N1—N2—C3155.1 (2)C13—C14—C19—O2112.1 (5)
C5—N1—N2—C24152.2 (2)C15—C14—C19—O2013.2 (4)
C6—N1—N2—C2463.1 (3)C13—C14—C19—O20168.7 (3)
C13—N36—C34—O353.2 (5)O33—C5—C4—C3179.8 (3)
C13—N36—C34—C10175.5 (2)N1—C5—C4—C31.7 (3)
O35—C34—C10—C11167.4 (3)O33—C5—C4—C3156.3 (4)
N36—C34—C10—C1111.3 (4)N1—C5—C4—C31125.1 (3)
O35—C34—C10—C912.0 (4)O33—C5—C4—C2861.7 (4)
N36—C34—C10—C9169.3 (2)N1—C5—C4—C28116.9 (3)
C9—C10—C11—C121.5 (4)C5—N1—C6—C774.6 (3)
C34—C10—C11—C12179.2 (2)N2—N1—C6—C765.5 (3)
N2—N1—C5—O33173.7 (2)C12—C7—C6—N1102.1 (3)
C6—N1—C5—O3330.7 (4)C8—C7—C6—N178.4 (3)
N2—N1—C5—C45.0 (3)N1—N2—C3—O32168.1 (3)
C6—N1—C5—C4147.9 (2)C24—N2—C3—O3228.6 (5)
C7—C8—C9—C100.3 (4)N1—N2—C3—C411.2 (3)
C11—C10—C9—C81.1 (4)C24—N2—C3—C4150.8 (3)
C34—C10—C9—C8179.5 (2)C5—C4—C3—O32171.4 (3)
C15—C14—C13—C180.5 (4)C31—C4—C3—O3246.0 (5)
C19—C14—C13—C18177.5 (2)C28—C4—C3—O3270.7 (4)
C15—C14—C13—N36179.0 (2)C5—C4—C3—N27.9 (3)
C19—C14—C13—N360.9 (4)C31—C4—C3—N2133.3 (3)
C34—N36—C13—C1819.5 (4)C28—C4—C3—N2110.0 (3)
C34—N36—C13—C14162.1 (3)C3—N2—C24—C2575.9 (4)
C9—C8—C7—C121.3 (4)N1—N2—C24—C2560.9 (3)
C9—C8—C7—C6178.2 (2)N2—C24—C25—C26178.8 (3)
C15—C16—C17—C181.0 (5)C5—C4—C28—C29133.4 (4)
C16—C17—C18—C131.0 (4)C3—C4—C28—C29113.8 (4)
C14—C13—C18—C170.2 (4)C31—C4—C28—C298.3 (5)
N36—C13—C18—C17178.2 (3)C5—C4—C31—C30113.4 (4)
C10—C11—C12—C70.5 (4)C3—C4—C31—C30129.0 (4)
C8—C7—C12—C110.9 (4)C28—C4—C31—C308.0 (5)
C6—C7—C12—C11178.6 (2)C24—C25—C26—C27173.9 (3)
C17—C16—C15—C140.2 (5)C4—C28—C29—C3023.1 (7)
C13—C14—C15—C160.6 (4)C28—C29—C30—C3128.8 (8)
C19—C14—C15—C16177.6 (3)C4—C31—C30—C2922.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N36—H36···O210.95 (4)1.86 (4)2.686 (3)144 (3)
O20—H20···O33i0.83 (4)1.79 (4)2.611 (3)169 (4)
Symmetry code: (i) x+1, y+1/2, z+1/2.
(III) 2-{4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]amilinocarbonyl} benzoic acid monohydrate top
Crystal data top
C26H29N3O5·H2OF(000) = 1024
Mr = 481.54Dx = 1.300 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 18.681 (1) ÅCell parameters from 25 reflections
b = 9.565 (1) Åθ = 40–50°
c = 14.837 (1) ŵ = 0.76 mm1
β = 111.904 (7)°T = 293 K
V = 2459.7 (3) Å3Platelet, colourless
Z = 40.26 × 0.11 × 0.07 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 71.9°, θmin = 2.6°
θ/2θ scansh = 2321
Absorption correction: ψ-scan
(North et al., 1968)
k = 711
Tmin = 0.826, Tmax = 0.948l = 018
6162 measured reflections3 standard reflections every 200 reflections
4835 independent reflections intensity decay: 4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0704P)2 + 0.7853P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.008
4835 reflectionsΔρmax = 0.36 e Å3
333 parametersΔρmin = 0.28 e Å3
5 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0016 (2)
Crystal data top
C26H29N3O5·H2OV = 2459.7 (3) Å3
Mr = 481.54Z = 4
Monoclinic, P21/cCu Kα radiation
a = 18.681 (1) ŵ = 0.76 mm1
b = 9.565 (1) ÅT = 293 K
c = 14.837 (1) Å0.26 × 0.11 × 0.07 mm
β = 111.904 (7)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3166 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(North et al., 1968)
Rint = 0.013
Tmin = 0.826, Tmax = 0.9483 standard reflections every 200 reflections
6162 measured reflections intensity decay: 4%
4835 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0495 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.36 e Å3
4835 reflectionsΔρmin = 0.28 e Å3
333 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*/UeqOcc. (<1)
N10.20910 (10)0.65699 (18)0.24187 (13)0.0450 (4)
N20.21551 (11)0.50822 (19)0.23485 (15)0.0520 (5)
N360.47146 (11)0.70613 (19)0.18844 (13)0.0444 (4)
O200.73325 (10)0.8984 (2)0.36369 (14)0.0631 (5)
O210.61993 (10)0.9142 (2)0.24154 (13)0.0739 (6)
O320.14828 (13)0.32933 (18)0.20050 (18)0.0850 (7)
O330.13980 (10)0.82122 (17)0.19702 (15)0.0660 (5)
O350.45948 (9)0.92269 (15)0.24674 (11)0.0534 (4)
O370.80719 (12)0.9319 (2)0.24565 (18)0.0747 (6)
C30.16194 (15)0.4545 (3)0.2033 (2)0.0587 (6)
C40.12390 (13)0.5729 (2)0.17191 (18)0.0516 (6)
C50.15534 (13)0.6992 (2)0.20510 (17)0.0476 (5)
C60.28283 (12)0.7339 (2)0.21603 (16)0.0461 (5)
C70.33114 (12)0.7256 (2)0.10923 (16)0.0424 (5)
C80.33048 (13)0.8342 (2)0.04800 (17)0.0498 (6)
C90.37475 (13)0.8312 (2)0.05066 (17)0.0491 (6)
C100.42171 (12)0.7168 (2)0.08979 (16)0.0412 (5)
C110.42244 (12)0.6065 (2)0.02945 (16)0.0441 (5)
C120.37805 (13)0.6109 (2)0.06867 (17)0.0447 (5)
C130.54829 (12)0.7636 (2)0.35450 (15)0.0405 (5)
C140.62581 (12)0.8059 (2)0.38871 (15)0.0413 (5)
C150.67317 (13)0.7757 (2)0.48425 (16)0.0482 (5)
C160.64443 (15)0.7061 (2)0.54480 (17)0.0534 (6)
C170.56916 (15)0.6604 (3)0.51045 (18)0.0546 (6)
C180.52165 (13)0.6880 (2)0.41534 (17)0.0492 (6)
C190.65765 (13)0.8791 (2)0.32326 (17)0.0461 (5)
C240.24654 (16)0.4375 (3)0.2992 (2)0.0681 (8)
C250.20546 (19)0.4738 (4)0.4042 (3)0.0942 (11)
C260.1245 (4)0.3987 (8)0.4314 (4)0.0898 (11)0.57
C270.0830 (4)0.4083 (7)0.5413 (4)0.0898 (11)0.57
C280.15115 (17)0.5785 (3)0.0595 (2)0.0712 (8)
C290.0881 (5)0.6323 (15)0.0352 (10)0.129 (3)0.63
C300.0184 (6)0.5929 (11)0.1157 (7)0.129 (3)0.63
C310.03508 (15)0.5652 (3)0.2068 (2)0.0722 (8)
C26'0.1175 (5)0.4801 (9)0.4639 (6)0.0898 (11)0.43
C27'0.0940 (5)0.3306 (9)0.4895 (6)0.0898 (11)0.43
C29'0.0755 (10)0.581 (3)0.0424 (19)0.129 (3)0.37
C30'0.0151 (11)0.523 (2)0.1257 (13)0.129 (3)0.37
C340.49034 (12)0.8070 (2)0.25730 (16)0.0417 (5)
H6A0.27200.83120.23440.055*
H6B0.31190.69560.25250.055*
H80.29940.91160.07370.060*
H90.37290.90530.09030.059*
H110.45310.52880.05530.053*
H120.37950.53630.10820.054*
H150.72470.80290.50740.058*
H160.67610.69000.60920.064*
H170.55030.61120.55100.065*
H180.47110.65530.39190.059*
H200.753 (2)0.925 (4)0.316 (3)0.111 (13)*
H24A0.24340.33730.29140.082*
H24B0.30060.46170.28000.082*
H25A0.23310.43840.44330.113*
H25B0.19930.57420.41320.113*
H26A0.13170.30160.41110.108*0.57
H26B0.09430.44440.39900.108*0.57
H27A0.03370.36300.56020.135*0.57
H27B0.11350.36310.57250.135*0.57
H27C0.07580.50470.56050.135*0.57
H28A0.16540.48580.03230.085*
H28B0.19580.63910.03300.085*
H29A0.09160.73310.02800.155*0.63
H29B0.08870.59140.02490.155*0.63
H30A0.01940.66730.12830.155*0.63
H30B0.00330.50950.09870.155*0.63
H26C0.09040.52000.42550.108*0.43
H26D0.10660.53600.52200.108*0.43
H27D0.03960.32630.52680.135*0.43
H27E0.10570.27700.43100.135*0.43
H27F0.12170.29300.52700.135*0.43
H29C0.08080.52660.01500.155*0.37
H29D0.06260.67620.03190.155*0.37
H30C0.03480.56000.13190.155*0.37
H30D0.01380.42170.12120.155*0.37
H31A0.01100.63540.25590.087*
H31B0.01640.47360.23330.087*
H360.4957 (14)0.619 (3)0.2035 (18)0.055 (7)*
H37A0.8276 (19)1.002 (4)0.231 (2)0.094 (12)*
H37B0.8247 (19)0.850 (4)0.235 (2)0.097 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0445 (10)0.0367 (9)0.0517 (11)0.0056 (8)0.0155 (9)0.0038 (8)
N20.0529 (11)0.0372 (10)0.0684 (13)0.0032 (8)0.0254 (10)0.0078 (9)
N360.0489 (10)0.0348 (9)0.0436 (10)0.0041 (8)0.0103 (8)0.0006 (8)
O200.0503 (10)0.0775 (13)0.0597 (11)0.0114 (9)0.0185 (8)0.0043 (9)
O210.0600 (11)0.1109 (16)0.0482 (10)0.0076 (10)0.0171 (9)0.0178 (11)
O320.0988 (15)0.0388 (10)0.136 (2)0.0097 (10)0.0649 (15)0.0013 (11)
O330.0706 (11)0.0418 (9)0.0971 (14)0.0047 (8)0.0447 (11)0.0038 (9)
O350.0586 (10)0.0370 (8)0.0547 (10)0.0065 (7)0.0096 (8)0.0026 (7)
O370.0782 (13)0.0483 (11)0.1174 (19)0.0002 (10)0.0595 (13)0.0083 (12)
C30.0582 (14)0.0439 (13)0.0753 (18)0.0030 (11)0.0265 (13)0.0015 (12)
C40.0483 (12)0.0453 (12)0.0612 (15)0.0015 (10)0.0205 (11)0.0052 (11)
C50.0440 (12)0.0425 (12)0.0549 (14)0.0003 (9)0.0168 (10)0.0022 (10)
C60.0428 (11)0.0435 (12)0.0508 (13)0.0065 (9)0.0161 (10)0.0019 (10)
C70.0391 (11)0.0373 (11)0.0494 (13)0.0061 (8)0.0150 (10)0.0005 (9)
C80.0460 (12)0.0365 (11)0.0587 (15)0.0043 (9)0.0102 (11)0.0002 (10)
C90.0513 (13)0.0372 (11)0.0517 (14)0.0049 (10)0.0110 (11)0.0061 (10)
C100.0400 (11)0.0341 (10)0.0480 (12)0.0037 (8)0.0146 (9)0.0008 (9)
C110.0465 (12)0.0326 (10)0.0525 (13)0.0014 (9)0.0174 (10)0.0027 (9)
C120.0501 (12)0.0346 (11)0.0486 (13)0.0014 (9)0.0176 (10)0.0024 (9)
C130.0442 (11)0.0344 (10)0.0442 (12)0.0039 (9)0.0181 (9)0.0024 (9)
C140.0456 (11)0.0358 (10)0.0429 (12)0.0026 (9)0.0171 (9)0.0037 (9)
C150.0493 (13)0.0473 (13)0.0446 (13)0.0045 (10)0.0135 (10)0.0029 (10)
C160.0665 (15)0.0516 (13)0.0401 (12)0.0091 (11)0.0174 (11)0.0031 (10)
C170.0681 (16)0.0496 (13)0.0551 (14)0.0098 (12)0.0335 (13)0.0095 (11)
C180.0485 (12)0.0452 (12)0.0573 (15)0.0057 (10)0.0237 (11)0.0047 (11)
C190.0480 (12)0.0429 (12)0.0469 (13)0.0015 (10)0.0172 (10)0.0040 (10)
C240.0651 (16)0.0517 (15)0.097 (2)0.0040 (12)0.0405 (16)0.0197 (15)
C250.077 (2)0.120 (3)0.091 (2)0.003 (2)0.0370 (19)0.051 (2)
C260.086 (2)0.107 (4)0.063 (3)0.002 (2)0.013 (2)0.0032 (18)
C270.086 (2)0.107 (4)0.063 (3)0.002 (2)0.013 (2)0.0032 (18)
C280.0757 (18)0.0744 (19)0.0662 (18)0.0026 (15)0.0297 (15)0.0116 (15)
C290.090 (3)0.200 (10)0.118 (3)0.021 (5)0.064 (3)0.025 (6)
C300.090 (3)0.200 (10)0.118 (3)0.021 (5)0.064 (3)0.025 (6)
C310.0486 (14)0.0685 (17)0.096 (2)0.0054 (13)0.0222 (14)0.0082 (16)
C26'0.086 (2)0.107 (4)0.063 (3)0.002 (2)0.013 (2)0.0032 (18)
C27'0.086 (2)0.107 (4)0.063 (3)0.002 (2)0.013 (2)0.0032 (18)
C29'0.090 (3)0.200 (10)0.118 (3)0.021 (5)0.064 (3)0.025 (6)
C30'0.090 (3)0.200 (10)0.118 (3)0.021 (5)0.064 (3)0.025 (6)
C340.0433 (11)0.0338 (10)0.0480 (12)0.0008 (9)0.0172 (10)0.0006 (9)
Geometric parameters (Å, º) top
N1—N21.429 (2)C26—C271.525 (7)
N1—C51.371 (3)C26—H26A0.9700
N1—C61.480 (3)C26—H26B0.9700
N2—C31.354 (3)C27—H27A0.9600
N36—C101.415 (3)C27—H27B0.9600
N36—C341.353 (3)C27—H27C0.9600
N36—H360.93 (3)C26'—C27'1.503 (10)
O20—C191.325 (3)C26'—H26C0.9700
O20—H200.94 (4)C26'—H26D0.9700
O21—C191.201 (3)C27'—H27D0.9600
O32—C31.228 (3)C27'—H27E0.9600
O33—C51.219 (3)C27'—H27F0.9600
O35—C341.231 (2)C13—C181.386 (3)
C31—C30'1.444 (13)C13—C141.403 (3)
C31—C301.519 (7)C13—C341.503 (3)
C31—C41.545 (3)C7—C81.383 (3)
C31—H31A0.9700C7—C121.393 (3)
C31—H31B0.9700C7—C61.505 (3)
C28—C291.449 (9)C6—H6A0.9700
C28—C29'1.527 (12)C6—H6B0.9700
C28—C41.552 (4)C14—C151.393 (3)
C28—H28A0.9700C14—C191.489 (3)
C28—H28B0.9700C11—C121.381 (3)
C24—N21.455 (3)C11—C101.387 (3)
C24—C251.498 (4)C11—H110.9300
C24—H24A0.9700C8—C91.387 (3)
C24—H24B0.9700C8—H80.9300
C25—C26'1.550 (8)C5—C41.505 (3)
C25—C261.586 (7)C15—C161.378 (3)
C25—H25A0.9700C15—H150.9300
C25—H25B0.9700C9—C101.387 (3)
C30—C291.450 (9)C9—H90.9300
C30—H30A0.9700C12—H120.9300
C30—H30B0.9700C16—C171.376 (4)
C29—H29A0.9700C16—H160.9300
C29—H29B0.9700C17—C181.384 (3)
C30'—C29'1.438 (13)C17—H170.9300
C30'—H30C0.9700C18—H180.9300
C30'—H30D0.9700C4—C31.500 (3)
C29'—H29C0.9700O37—H37A0.84 (4)
C29'—H29D0.9700O37—H37B0.89 (4)
C30'—C31—C4108.3 (9)C26'—C27'—H27E109.5
C30—C31—C4104.2 (5)H27D—C27'—H27E109.5
C30'—C31—H31A129.0C26'—C27'—H27F109.5
C30—C31—H31A110.9H27D—C27'—H27F109.5
C4—C31—H31A110.9H27E—C27'—H27F109.5
C30'—C31—H31B85.4C19—O20—H20110 (2)
C30—C31—H31B110.9C34—N36—C10128.00 (18)
C4—C31—H31B110.9C34—N36—H36119.1 (15)
H31A—C31—H31B108.9C10—N36—H36112.7 (15)
C29—C28—C4108.0 (6)C3—N2—N1110.53 (18)
C29'—C28—C4103.1 (10)C3—N2—C24125.2 (2)
C29—C28—H28A110.1N1—N2—C24117.2 (2)
C29'—C28—H28A94.1C5—N1—N2108.58 (17)
C4—C28—H28A110.1C5—N1—C6119.97 (18)
C29—C28—H28B110.1N2—N1—C6115.57 (17)
C29'—C28—H28B129.3C18—C13—C14119.2 (2)
C4—C28—H28B110.1C18—C13—C34117.64 (19)
H28A—C28—H28B108.4C14—C13—C34122.97 (19)
N2—C24—C25113.6 (2)O35—C34—N36124.6 (2)
N2—C24—H24A108.9O35—C34—C13120.38 (19)
C25—C24—H24A108.9N36—C34—C13114.81 (17)
N2—C24—H24B108.9C8—C7—C12117.8 (2)
C25—C24—H24B108.9C8—C7—C6120.20 (19)
H24A—C24—H24B107.7C12—C7—C6122.0 (2)
C24—C25—C26'128.7 (4)N1—C6—C7112.40 (17)
C24—C25—C26103.3 (3)N1—C6—H6A109.1
C24—C25—H25A111.1C7—C6—H6A109.1
C26'—C25—H25A111.1N1—C6—H6B109.1
C26—C25—H25A111.1C7—C6—H6B109.1
C24—C25—H25B111.1H6A—C6—H6B107.9
C26'—C25—H25B80.6C15—C14—C13119.1 (2)
C26—C25—H25B111.1C15—C14—C19120.3 (2)
H25A—C25—H25B109.1C13—C14—C19120.59 (19)
C29—C30—C31111.0 (7)C12—C11—C10120.70 (19)
C29—C30—H30A109.4C12—C11—H11119.6
C31—C30—H30A109.4C10—C11—H11119.6
C29—C30—H30B109.4C7—C8—C9122.0 (2)
C31—C30—H30B109.4C7—C8—H8119.0
H30A—C30—H30B108.0C9—C8—H8119.0
C28—C29—C30105.4 (8)O33—C5—N1123.9 (2)
C28—C29—H29A110.7O33—C5—C4126.9 (2)
C30—C29—H29A110.7N1—C5—C4109.08 (19)
C28—C29—H29B110.6C16—C15—C14120.6 (2)
C30—C29—H29B110.7C16—C15—H15119.7
H29A—C29—H29B108.8C14—C15—H15119.7
C29'—C30'—C31104.1 (14)O21—C19—O20122.9 (2)
C29'—C30'—H30C110.9O21—C19—C14124.3 (2)
C31—C30'—H30C110.9O20—C19—C14112.8 (2)
C29'—C30'—H30D110.9C10—C9—C8119.6 (2)
C31—C30'—H30D110.9C10—C9—H9120.2
H30C—C30'—H30D108.9C8—C9—H9120.2
C30'—C29'—C28109.2 (14)C11—C10—C9119.1 (2)
C30'—C29'—H29C109.8C11—C10—N36116.89 (18)
C28—C29'—H29C109.8C9—C10—N36123.97 (19)
C30'—C29'—H29D109.8C11—C12—C7120.9 (2)
C28—C29'—H29D109.8C11—C12—H12119.6
H29C—C29'—H29D108.3C7—C12—H12119.6
C27—C26—C25107.5 (5)C17—C16—C15120.3 (2)
C27—C26—H26A110.2C17—C16—H16119.8
C25—C26—H26A110.2C15—C16—H16119.8
C27—C26—H26B110.2C16—C17—C18119.7 (2)
C25—C26—H26B110.2C16—C17—H17120.2
H26A—C26—H26B108.5C18—C17—H17120.2
C26—C27—H27A109.5C17—C18—C13120.9 (2)
C26—C27—H27B109.5C17—C18—H18119.5
H27A—C27—H27B109.5C13—C18—H18119.5
C26—C27—H27C109.5C3—C4—C5102.53 (19)
H27A—C27—H27C109.5C3—C4—C31115.7 (2)
H27B—C27—H27C109.5C5—C4—C31115.5 (2)
C27'—C26'—C25104.8 (6)C3—C4—C28110.9 (2)
C27'—C26'—H26C110.8C5—C4—C28108.2 (2)
C25—C26'—H26C110.8C31—C4—C28104.0 (2)
C27'—C26'—H26D110.8O32—C3—N2124.8 (2)
C25—C26'—H26D110.8O32—C3—C4126.7 (2)
H26C—C26'—H26D108.9N2—C3—C4108.5 (2)
C26'—C27'—H27D109.5H37A—O37—H37B116 (3)
N2—C24—C25—C26'46.7 (6)C7—C8—C9—C100.5 (4)
N2—C24—C25—C2671.0 (4)C12—C11—C10—C91.0 (3)
C4—C31—C30—C297.0 (8)C12—C11—C10—N36177.3 (2)
C4—C28—C29—C3028.0 (9)C8—C9—C10—C111.0 (3)
C31—C30—C29—C2821.9 (10)C8—C9—C10—N36177.2 (2)
C4—C31—C30'—C29'31.8 (14)C34—N36—C10—C11168.6 (2)
C31—C30'—C29'—C2834.1 (18)C34—N36—C10—C99.7 (4)
C4—C28—C29'—C30'22.6 (17)C10—C11—C12—C70.4 (3)
C24—C25—C26—C27170.6 (5)C8—C7—C12—C110.1 (3)
C24—C25—C26'—C27'80.2 (8)C6—C7—C12—C11179.3 (2)
C26—C25—C26'—C27'33.3 (6)C14—C15—C16—C172.6 (3)
C25—C24—N2—C394.5 (3)C15—C16—C17—C181.8 (4)
C25—C24—N2—N153.4 (3)C16—C17—C18—C131.3 (3)
C3—N2—N1—C55.9 (3)C14—C13—C18—C173.5 (3)
C24—N2—N1—C5158.2 (2)C34—C13—C18—C17171.3 (2)
C3—N2—N1—C6144.0 (2)O33—C5—C4—C3178.7 (3)
C24—N2—N1—C663.6 (3)N1—C5—C4—C34.9 (2)
C10—N36—C34—O358.7 (4)O33—C5—C4—C3151.9 (4)
C10—N36—C34—C13176.98 (19)N1—C5—C4—C31131.7 (2)
C18—C13—C34—O3594.0 (3)O33—C5—C4—C2864.1 (3)
C14—C13—C34—O3580.7 (3)N1—C5—C4—C28112.3 (2)
C18—C13—C34—N3680.6 (2)C30'—C31—C4—C3104.2 (9)
C14—C13—C34—N36104.7 (2)C30—C31—C4—C3131.6 (5)
C5—N1—C6—C763.8 (3)C30'—C31—C4—C5136.0 (9)
N2—N1—C6—C769.3 (2)C30—C31—C4—C5108.7 (5)
C8—C7—C6—N198.4 (2)C30'—C31—C4—C2817.7 (9)
C12—C7—C6—N182.2 (3)C30—C31—C4—C289.7 (5)
C18—C13—C14—C152.7 (3)C29—C28—C4—C3148.6 (6)
C34—C13—C14—C15171.93 (19)C29'—C28—C4—C3127.7 (11)
C18—C13—C14—C19175.96 (19)C29—C28—C4—C599.8 (6)
C34—C13—C14—C199.5 (3)C29'—C28—C4—C5120.6 (11)
C12—C7—C8—C90.1 (3)C29—C28—C4—C3123.5 (6)
C6—C7—C8—C9179.4 (2)C29'—C28—C4—C312.7 (11)
N2—N1—C5—O33176.4 (2)N1—N2—C3—O32171.6 (3)
C6—N1—C5—O3340.4 (3)C24—N2—C3—O3221.9 (4)
N2—N1—C5—C40.1 (2)N1—N2—C3—C49.1 (3)
C6—N1—C5—C4136.1 (2)C24—N2—C3—C4158.7 (2)
C13—C14—C15—C160.4 (3)C5—C4—C3—O32172.3 (3)
C19—C14—C15—C16179.0 (2)C31—C4—C3—O3245.6 (4)
C15—C14—C19—O21176.5 (2)C28—C4—C3—O3272.5 (3)
C13—C14—C19—O214.9 (3)C5—C4—C3—N28.4 (3)
C15—C14—C19—O205.3 (3)C31—C4—C3—N2135.0 (2)
C13—C14—C19—O20173.33 (19)C28—C4—C3—N2106.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O370.95 (4)1.70 (4)2.623 (3)163 (4)
O37—H37A···O33i0.84 (4)1.93 (4)2.759 (3)171 (4)
O37—H37B···O32ii0.89 (4)1.91 (4)2.793 (3)174 (3)
N36—H36···O35iii0.93 (3)2.08 (3)3.002 (2)171 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1, z; (iii) x+1, y1/2, z+1/2.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC26H28N2O5C26H29N3O5C26H29N3O5·H2O
Mr448.50463.52481.54
Crystal system, space groupTriclinic, P1Monoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293293
a, b, c (Å)10.530 (1), 11.469 (1), 11.491 (1)16.122 (1), 12.682 (1), 11.920 (1)18.681 (1), 9.565 (1), 14.837 (1)
α, β, γ (°)109.589 (8), 112.690 (8), 97.640 (9)90, 97.139 (7), 9090, 111.904 (7), 90
V3)1150.02 (18)2418.3 (3)2459.7 (3)
Z244
Radiation typeCu KαCu KαCu Kα
µ (mm1)0.730.730.76
Crystal size (mm)0.31 × 0.29 × 0.230.29 × 0.10 × 0.030.26 × 0.11 × 0.07
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionψ-scan
(North et al., 1968)
ψ-scan
(North et al., 1968)
ψ-scan
(North et al., 1968)
Tmin, Tmax0.804, 0.8490.817, 0.9790.826, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections
4750, 4511, 3537 6842, 4757, 1972 6162, 4835, 3166
Rint0.0430.0260.013
(sin θ/λ)max1)0.6170.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.152, 1.04 0.053, 0.164, 0.96 0.049, 0.151, 1.02
No. of reflections451147574835
No. of parameters302315333
No. of restraints005
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.280.16, 0.190.36, 0.28

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1992), CAD-4 EXPRESS, PLATON (Spek, 2000), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON, SHELXL97.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O33i0.90 (3)1.79 (3)2.687 (3)174 (3)
Symmetry code: (i) x, y1, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N36—H36···O210.95 (4)1.86 (4)2.686 (3)144 (3)
O20—H20···O33i0.83 (4)1.79 (4)2.611 (3)169 (4)
Symmetry code: (i) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O370.95 (4)1.70 (4)2.623 (3)163 (4)
O37—H37A···O33i0.84 (4)1.93 (4)2.759 (3)171 (4)
O37—H37B···O32ii0.89 (4)1.91 (4)2.793 (3)174 (3)
N36—H36···O35iii0.93 (3)2.08 (3)3.002 (2)171 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1, z; (iii) x+1, y1/2, z+1/2.
 

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