Download citation
Download citation
link to html
The title compounds, (Z)-4-(2,6-dichloro­phenyl­diazen­yl)-6-{[1,3-dihydr­oxy-2-(hydroxy­meth­yl)propan-2-ylamino]methyl­ene}-2-methoxy­cyclo­hexa-2,4-dienone, C18H19Cl2N3O5, (I), (Z)-6-{[1,3-dihydr­oxy-2-(hydroxy­meth­yl)propan-2-yl­amino]­methyl­ene}-2-meth­oxy-4-(3-methoxy­phenyl­diazen­yl)cyclo­hexa-2,4-dienone, C19H23N3O6, (II), and (Z)-6-{[1,3-di­hydr­oxy-2-(hydroxy­meth­yl)propan-2-ylamino]methyl­ene}-2-meth­oxy-4-(4-methoxy­phenyl­diazen­yl)cyclo­hexa-2,4-dienone, C19H23N3O6, (III), all adopt the keto–amine tautomeric form, and the hydroxy H atoms are located on the N atom in all three compounds. Strong intra­molecular N—H...O hydrogen bonds arise as a result of the shifts achieved by the hydroxy H atoms of the Schiff bases to the N atoms. Positional disorder was observed in mol­ecules (II) and (III). In all three compounds, C—H...π and π–π inter­actions affect the packing of the mol­ecules. The compounds exhibit trans geometry with respect to the azo N=N double bond, and the mol­ecules are linked by O—H...O hydrogen bonds to form three-dimensional networks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106005026/hj1088sup1.cif
Contains datablocks global, II, III, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005026/hj1088Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005026/hj1088IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005026/hj1088IIIsup4.hkl
Contains datablock III

CCDC references: 605679; 605680; 605681

Comment top

Azo compounds are the most widely used class of dyes owing to their versatile application in various fields, such as the dyeing of textiles and fibers, the coloring of different materials, and high-technology areas, such as electro-optical devices and ink-jet printers (Peters & Freeman, 1991). Most Schiff bases have antibacterial, anticancer, antinflammatory and antitoxic properties (Williams, 1972). Two characteristic properties of Schiff bases are photochromism and thermochromism (Cohen et al., 1964; Moustakali-Mavridis et al., 1978). These properties are caused by proton transfer from the hydroxy O atom to the imine N atom (Hadjoudis et al., 1987; Xu et al., 1994). As part of a general study of the crystal chemistry of dyes, and to provide templates for molecular-modelling studies, the crystal structures of the title compounds, (I), (II) and (III), have been determined. The molecular structures of (I), (II) and (III), with the atom-labelling schemes, are shown in Figs. 1, 2 and 3, respectively, and selected bond lengths and angles are given in Tables 1, 3 and 5, respectively.

In all three molecules (I), (II) and (III), the keto–amine tautomer is favoured over the phenol–imine form, as indicated by the C10—O3, C13—N3, C11—C13 and C10—C11 bond lengths (Figs. 1, 2 and 3, and Tables 1, 3 and 5). Furthermore, these data show that there are significant elongations of the C13—N3 bond and contraction of the C10—O3 bond. A similar effect was observed for 4-[(3-chloropheny)diazeniyl]-2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one [C10—O3 = 1.286 (2) Å, C13—N3 = 1.298 (3) Å, C11—C13 = 1.411 (3) Å and C10—C11 = 1.436 (3) Å; Odabaşoǧlu et al., 2003]. The H atom was located on N1, thus confirming a preference for the keto–amine tautomer in the solid state. The N1—C1 and N2—C7 bond lengths are approximately the same in (I), (II) and (III), and these lengths indicate single-bond character, whereas the NN bond lengths are indicative of significant double-bond character. The high s.u. values and high displacement parameters of some atoms in the molecules of both (II) and (III) are probably caused by positional and orientational disorder. In (II), C18 is observed at two different positions owing to a positional disorder, with occupancy factors of 0.64 (7) and 0.36 (7). In (III), atom O1 shows positional disorder with occupancy factors of 0.409 (7) and 0.591 (7). At the same time, the phenyl rings also show orientational disorder with the same occupancy factors (Fig. 3).

In (I), the C—Cl bond distance is consistent with that in 5-(2-chlorophenyldiazenyl)salicylaldehyde and 4-(2-chlorophenyldiazenyl)- 2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one (Albayrak et al., 2004). The dihedral angles between the C1–C6 and C7–C12 rings are 58.91 (13), 8.89 (11) and 21.57 (3)° (the average of the two angles for the orientationally disordered phenyl ring) for (I), (II) and (III), respectively.

The intra- and intermolecular hydrogen bonds are shown in the packing diagram of (I), (II) and (III) in Figs. 4–6, respectively. In all three structure, these O—H···O hydrogen bonds generate edge-fused R22(5), R32(19) and R22(12) rings. Atom H33 bonded to N3 form a strong intramolecular hydrogen bond with atom O3, as observed in similar compounds (Odabaşoǧlu et al., 2003; Albayrak et al., 2004). In (I), (II) and (III), the molecules are linked by C—H···π interactions (Tables 2, 4 and 6, and Figs. 4–6). In addition to these interactions, all three compounds contain ππ interactions. Details of these ππ interactions are given in Table 7 and they are shown in Figs. 4–6.

Experimental top

Compounds (I), (II) and (III) were prepared as described in the literature (Odabaşoǧlu et al., Albayrak, Büyükgüngör & Lönnecke, 2003)?????? using o-vanillin, 2.6-dichloroaniline for (I), 3-methoxyaniline for (II), 4-methoxyaniline for (III) and tris(hydroxymethyl)aminomethane as starting materials. The product was crystallized from ethanol, and well shaped crystals were obtained by slow evaporation of a ethanol solution [yield 74%, m.p. 480–482 K for (I); yield 76%, m.p. 462–463 K for (II);

yield 78%, m.p. 489–490 K for (III)].

Refinement top

H atoms attached to N and O atoms were refined freely. All remaining H atoms were refined using a riding model, with C—H distances of 0.93–0.97 Å. In (III), the H atoms of C18 were refined at two different positions owing to disorder, with 0.5 occupancy for each component. The Uiso(H) values are 1.5Ueq(C) for the methyl H atoms and 1.2Ueq(C) for the remaining C-bound H atoms.

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. An ORTEP-3 (Farrugia, 1997) view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids. The dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. An ORTEP-3 (Farrugia, 1997) view of (II), with the atom-numbering scheme and 50% probability displacement ellipsoids. The dashed line indicates the intramolecular hydrogen bond.
[Figure 3] Fig. 3. An ORTEP-3 (Farrugia, 1997) view of (III), with the atom-numbering scheme and 50% probability displacement ellipsoids. The dashed line indicates the intramolecular hydrogen bond.
[Figure 4] Fig. 4. An ORTEP-3 (Farrugia, 1997) packing diagram of (I). Dashed lines indicate hydrogen bonds, C—H···π and ππ interactions. H atoms not involved in hydrogen bonding or C—H···π interactions have been omitted for clarity.
[Figure 5] Fig. 5. An ORTEP-3 (Farrugia, 1997) packing diagram of (II). Dashed lines indicate hydrogen bonds, C—H···π and ππ interactions. H atoms not involved in hydrogen bonding or C—H···π interactions have been omitted for clarity.
[Figure 6] Fig. 6. An ORTEP-3 (Farrugia, 1997) packing diagram of (III). Dashed lines indicate hydrogen bonds, C—H···π and ππ interactions. H atoms not involved in hydrogen bonding or C—H···π interactions have been omitted for clarity.
(I) (Z)-4-(2,6-dichlorophenyldiazenyl)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan- 2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone top
Crystal data top
C18H19Cl2N3O5F(000) = 888
Mr = 428.26Dx = 1.474 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12750 reflections
a = 16.8445 (15) Åθ = 1.9–28.4°
b = 10.7259 (5) ŵ = 0.37 mm1
c = 11.1126 (9) ÅT = 296 K
β = 106.037 (7)°Stick, red
V = 1929.6 (2) Å30.78 × 0.33 × 0.05 mm
Z = 4
Data collection top
STOE IPDS-II
diffractometer
3782 independent reflections
Radiation source: fine-focus sealed tube2715 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 2020
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1113
Tmin = 0.871, Tmax = 0.977l = 1312
10068 measured reflections
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) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0754P)2 + 0.1273P]
where P = (Fo2 + 2Fc2)/3
3782 reflections(Δ/σ)max < 0.001
269 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C18H19Cl2N3O5V = 1929.6 (2) Å3
Mr = 428.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.8445 (15) ŵ = 0.37 mm1
b = 10.7259 (5) ÅT = 296 K
c = 11.1126 (9) Å0.78 × 0.33 × 0.05 mm
β = 106.037 (7)°
Data collection top
STOE IPDS-II
diffractometer
3782 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
2715 reflections with I > 2σ(I)
Tmin = 0.871, Tmax = 0.977Rint = 0.056
10068 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.31 e Å3
3782 reflectionsΔρmin = 0.36 e Å3
269 parameters
Special details top

Experimental. 135 frames, detector distance = 110 mm

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
C10.58033 (15)0.5549 (2)0.2111 (2)0.0460 (6)
C20.50018 (17)0.5839 (3)0.2154 (3)0.0551 (7)
C30.44778 (19)0.6504 (3)0.1201 (3)0.0706 (9)
H30.39480.66980.12430.085*
C40.4730 (2)0.6877 (3)0.0203 (3)0.0801 (10)
H40.43750.73430.04250.096*
C50.5509 (2)0.6575 (3)0.0099 (3)0.0690 (8)
H50.56770.68200.05950.083*
C60.60314 (17)0.5899 (3)0.1060 (2)0.0544 (6)
C70.70689 (13)0.4967 (2)0.5165 (2)0.0389 (5)
C80.71827 (13)0.5702 (2)0.6250 (2)0.0405 (5)
H80.69190.64700.61950.049*
C90.76720 (13)0.5310 (2)0.7379 (2)0.0393 (5)
C100.80919 (12)0.4135 (2)0.7498 (2)0.0350 (5)
C110.80026 (13)0.3442 (2)0.6365 (2)0.0362 (5)
C120.74816 (14)0.3857 (2)0.5217 (2)0.0399 (5)
H120.74170.33820.44960.048*
C130.84882 (13)0.2351 (2)0.6384 (2)0.0373 (5)
H130.84280.19090.56440.045*
C140.95897 (13)0.09159 (19)0.75662 (19)0.0340 (4)
C150.96751 (14)0.0380 (2)0.6337 (2)0.0399 (5)
H15A0.97010.10600.57740.048*
H15B1.01890.00820.64990.048*
C160.92724 (14)0.0049 (2)0.8336 (2)0.0389 (5)
H16A0.92450.03150.91220.047*
H16B0.87220.03210.78800.047*
C171.04417 (13)0.1429 (2)0.8285 (2)0.0403 (5)
H17A1.08170.07400.85870.048*
H17B1.06640.19240.77230.048*
C180.7495 (2)0.7156 (3)0.8462 (3)0.0683 (8)
H18A0.75980.74570.93050.102*
H18B0.69100.71210.80780.102*
H18C0.77450.77100.79940.102*
Cl10.46378 (5)0.52727 (10)0.33563 (8)0.0797 (3)
Cl20.70005 (5)0.54926 (9)0.09348 (8)0.0764 (3)
N10.63785 (13)0.4885 (2)0.31082 (19)0.0498 (5)
N20.65194 (12)0.55064 (18)0.40892 (19)0.0435 (5)
N30.90058 (11)0.19559 (17)0.73893 (18)0.0352 (4)
O10.78373 (12)0.59483 (17)0.84753 (16)0.0551 (5)
O30.85420 (10)0.37752 (14)0.85661 (14)0.0420 (4)
O41.03869 (11)0.21784 (17)0.93174 (15)0.0443 (4)
O50.98183 (12)0.10746 (16)0.85653 (19)0.0531 (5)
O60.90118 (12)0.04188 (16)0.57467 (18)0.0471 (4)
H330.9027 (16)0.237 (3)0.799 (3)0.051 (8)*
H441.0575 (17)0.280 (3)0.929 (3)0.050 (8)*
H550.979 (2)0.140 (3)0.920 (3)0.068 (10)*
H660.8821 (17)0.022 (3)0.513 (3)0.043 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0480 (13)0.0433 (13)0.0390 (12)0.0016 (10)0.0010 (10)0.0006 (10)
C20.0516 (14)0.0561 (15)0.0520 (15)0.0015 (12)0.0052 (12)0.0032 (12)
C30.0573 (17)0.0675 (19)0.075 (2)0.0084 (14)0.0016 (15)0.0042 (17)
C40.083 (2)0.066 (2)0.068 (2)0.0027 (17)0.0173 (17)0.0144 (17)
C50.083 (2)0.0666 (18)0.0476 (16)0.0127 (16)0.0010 (14)0.0128 (14)
C60.0557 (14)0.0570 (15)0.0447 (14)0.0117 (12)0.0042 (11)0.0016 (12)
C70.0376 (11)0.0376 (11)0.0389 (12)0.0030 (9)0.0060 (9)0.0064 (10)
C80.0388 (11)0.0363 (11)0.0444 (13)0.0076 (9)0.0084 (9)0.0028 (10)
C90.0399 (11)0.0387 (12)0.0391 (12)0.0051 (9)0.0107 (9)0.0013 (9)
C100.0335 (10)0.0360 (11)0.0352 (11)0.0001 (8)0.0093 (8)0.0016 (9)
C110.0391 (11)0.0331 (10)0.0349 (11)0.0014 (9)0.0076 (8)0.0016 (9)
C120.0433 (12)0.0390 (12)0.0343 (11)0.0014 (9)0.0056 (9)0.0010 (9)
C130.0429 (11)0.0336 (10)0.0346 (11)0.0022 (9)0.0091 (9)0.0014 (9)
C140.0403 (11)0.0279 (10)0.0331 (11)0.0047 (8)0.0092 (8)0.0025 (8)
C150.0478 (12)0.0375 (11)0.0354 (11)0.0075 (9)0.0130 (9)0.0024 (9)
C160.0497 (12)0.0339 (11)0.0335 (11)0.0009 (9)0.0118 (9)0.0023 (9)
C170.0434 (12)0.0372 (11)0.0397 (12)0.0016 (9)0.0106 (9)0.0034 (9)
C180.096 (2)0.0484 (15)0.0555 (16)0.0269 (15)0.0134 (15)0.0101 (13)
Cl10.0630 (5)0.1070 (7)0.0731 (5)0.0062 (4)0.0257 (4)0.0000 (5)
Cl20.0646 (5)0.1003 (6)0.0664 (5)0.0108 (4)0.0216 (4)0.0097 (4)
N10.0538 (12)0.0466 (11)0.0432 (11)0.0050 (9)0.0037 (9)0.0004 (9)
N20.0414 (10)0.0441 (10)0.0408 (11)0.0002 (8)0.0042 (8)0.0021 (9)
N30.0419 (10)0.0309 (9)0.0326 (9)0.0049 (7)0.0097 (7)0.0002 (8)
O10.0714 (11)0.0492 (10)0.0392 (9)0.0244 (8)0.0062 (8)0.0073 (8)
O30.0496 (9)0.0415 (9)0.0326 (8)0.0110 (7)0.0073 (7)0.0013 (7)
O40.0562 (10)0.0336 (9)0.0402 (9)0.0076 (8)0.0082 (7)0.0001 (7)
O50.0787 (13)0.0352 (9)0.0476 (10)0.0140 (8)0.0212 (9)0.0115 (8)
O60.0642 (11)0.0398 (9)0.0318 (9)0.0029 (8)0.0042 (8)0.0021 (7)
Geometric parameters (Å, º) top
C1—C61.378 (4)C13—N31.284 (3)
C1—C21.399 (4)C13—H130.9300
C1—N11.443 (3)C14—N31.464 (3)
C2—C31.375 (4)C14—C151.525 (3)
C2—Cl11.727 (3)C14—C161.530 (3)
C3—C41.354 (5)C14—C171.538 (3)
C3—H30.9300C15—O61.417 (3)
C4—C51.387 (5)C15—H15A0.9700
C4—H40.9300C15—H15B0.9700
C5—C61.386 (4)C16—O51.411 (3)
C5—H50.9300C16—H16A0.9700
C6—Cl21.732 (3)C16—H16B0.9700
C7—C121.372 (3)C17—O41.425 (3)
C7—C81.409 (3)C17—H17A0.9700
C7—N21.417 (3)C17—H17B0.9700
C8—C91.364 (3)C18—O11.417 (3)
C8—H80.9300C18—H18A0.9600
C9—O11.357 (3)C18—H18B0.9600
C9—C101.434 (3)C18—H18C0.9600
C10—O31.279 (3)N1—N21.243 (3)
C10—C111.434 (3)N3—H330.79 (3)
C11—C121.406 (3)O4—H440.74 (3)
C11—C131.425 (3)O5—H550.80 (4)
C12—H120.9300O6—H660.70 (3)
C6—C1—C2117.8 (2)N3—C14—C15113.15 (17)
C6—C1—N1120.0 (2)N3—C14—C16105.37 (17)
C2—C1—N1122.2 (2)C15—C14—C16112.28 (18)
C3—C2—C1120.6 (3)N3—C14—C17107.04 (17)
C3—C2—Cl1119.2 (2)C15—C14—C17107.13 (18)
C1—C2—Cl1120.0 (2)C16—C14—C17111.82 (18)
C4—C3—C2120.3 (3)O6—C15—C14112.68 (19)
C4—C3—H3119.9O6—C15—H15A109.1
C2—C3—H3119.9C14—C15—H15A109.1
C3—C4—C5121.2 (3)O6—C15—H15B109.1
C3—C4—H4119.4C14—C15—H15B109.1
C5—C4—H4119.4H15A—C15—H15B107.8
C6—C5—C4118.2 (3)O5—C16—C14108.52 (19)
C6—C5—H5120.9O5—C16—H16A110.0
C4—C5—H5120.9C14—C16—H16A110.0
C1—C6—C5122.0 (3)O5—C16—H16B110.0
C1—C6—Cl2119.3 (2)C14—C16—H16B110.0
C5—C6—Cl2118.8 (3)H16A—C16—H16B108.4
C12—C7—C8120.16 (19)O4—C17—C14111.17 (18)
C12—C7—N2126.5 (2)O4—C17—H17A109.4
C8—C7—N2113.35 (19)C14—C17—H17A109.4
C9—C8—C7121.3 (2)O4—C17—H17B109.4
C9—C8—H8119.3C14—C17—H17B109.4
C7—C8—H8119.3H17A—C17—H17B108.0
O1—C9—C8126.3 (2)O1—C18—H18A109.5
O1—C9—C10112.76 (19)O1—C18—H18B109.5
C8—C9—C10120.9 (2)H18A—C18—H18B109.5
O3—C10—C9120.1 (2)O1—C18—H18C109.5
O3—C10—C11123.37 (19)H18A—C18—H18C109.5
C9—C10—C11116.44 (18)H18B—C18—H18C109.5
C12—C11—C13119.0 (2)N2—N1—C1109.5 (2)
C12—C11—C10121.38 (19)N1—N2—C7116.28 (19)
C13—C11—C10119.47 (18)C13—N3—C14129.6 (2)
C7—C12—C11119.6 (2)C13—N3—H33114 (2)
C7—C12—H12120.2C14—N3—H33116 (2)
C11—C12—H12120.2C9—O1—C18118.02 (19)
N3—C13—C11122.2 (2)C17—O4—H44111 (2)
N3—C13—H13118.9C16—O5—H55107 (2)
C11—C13—H13118.9C15—O6—H66111 (2)
C6—C1—C2—C33.1 (4)C8—C7—C12—C111.6 (3)
N1—C1—C2—C3178.2 (3)N2—C7—C12—C11179.4 (2)
C6—C1—C2—Cl1172.6 (2)C13—C11—C12—C7174.0 (2)
N1—C1—C2—Cl16.2 (3)C10—C11—C12—C72.1 (3)
C1—C2—C3—C40.6 (5)C12—C11—C13—N3176.5 (2)
Cl1—C2—C3—C4175.1 (3)C10—C11—C13—N30.3 (3)
C2—C3—C4—C51.6 (5)N3—C14—C15—O678.6 (2)
C3—C4—C5—C61.2 (5)C16—C14—C15—O640.5 (2)
C2—C1—C6—C53.4 (4)C17—C14—C15—O6163.68 (17)
N1—C1—C6—C5177.7 (2)N3—C14—C16—O5178.82 (18)
C2—C1—C6—Cl2176.9 (2)C15—C14—C16—O557.6 (2)
N1—C1—C6—Cl21.9 (3)C17—C14—C16—O562.9 (2)
C4—C5—C6—C11.4 (4)N3—C14—C17—O446.1 (2)
C4—C5—C6—Cl2179.0 (2)C15—C14—C17—O4167.76 (17)
C12—C7—C8—C92.9 (4)C16—C14—C17—O468.8 (2)
N2—C7—C8—C9178.0 (2)C6—C1—N1—N2119.3 (3)
C7—C8—C9—O1178.7 (2)C2—C1—N1—N262.0 (3)
C7—C8—C9—C100.3 (4)C1—N1—N2—C7179.2 (2)
O1—C9—C10—O32.1 (3)C12—C7—N2—N12.7 (4)
C8—C9—C10—O3179.3 (2)C8—C7—N2—N1178.3 (2)
O1—C9—C10—C11175.4 (2)C11—C13—N3—C14175.4 (2)
C8—C9—C10—C113.2 (3)C15—C14—N3—C1310.7 (3)
O3—C10—C11—C12178.1 (2)C16—C14—N3—C13112.3 (2)
C9—C10—C11—C124.5 (3)C17—C14—N3—C13128.5 (2)
O3—C10—C11—C135.7 (3)C8—C9—O1—C182.0 (4)
C9—C10—C11—C13171.7 (2)C10—C9—O1—C18176.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.79 (3)1.90 (3)2.587 (2)144 (3)
O4—H44···O6i0.74 (3)2.04 (3)2.777 (3)174 (3)
O5—H55···O4ii0.80 (4)1.94 (4)2.740 (3)176 (3)
O6—H66···O1iii0.70 (3)2.25 (3)2.802 (2)137 (3)
O6—H66···O3iii0.70 (3)2.28 (3)2.923 (2)153 (3)
C17—H17A···G1iv0.97 (1)2.95 (1)3.798 (2)147 (1)
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+2, y, z+2; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z+1/2.
(II) (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxy- 4-(3-methoxyphenyldiazenyl)cyclohexa-2,4-dienone top
Crystal data top
C19H23N3O6F(000) = 824
Mr = 389.40Dx = 1.352 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13037 reflections
a = 16.3722 (11) Åθ = 1.8–28.9°
b = 10.4506 (5) ŵ = 0.10 mm1
c = 11.3239 (7) ÅT = 296 K
β = 99.180 (5)°Prism, red
V = 1912.7 (2) Å30.42 × 0.33 × 0.25 mm
Z = 4
Data collection top
STOE IPDS-II
diffractometer
3744 independent reflections
Radiation source: fine-focus sealed tube2778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 2020
Absorption correction: integration
STOE X-RED (Stoe & Cie, 2002)
k = 1212
Tmin = 0.970, Tmax = 0.982l = 1313
13464 measured reflections
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) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0982P)2 + 0.2314P]
where P = (Fo2 + 2Fc2)/3
3744 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.83 e Å3
3 restraintsΔρmin = 0.32 e Å3
Crystal data top
C19H23N3O6V = 1912.7 (2) Å3
Mr = 389.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.3722 (11) ŵ = 0.10 mm1
b = 10.4506 (5) ÅT = 296 K
c = 11.3239 (7) Å0.42 × 0.33 × 0.25 mm
β = 99.180 (5)°
Data collection top
STOE IPDS-II
diffractometer
3744 independent reflections
Absorption correction: integration
STOE X-RED (Stoe & Cie, 2002)
2778 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.982Rint = 0.040
13464 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0533 restraints
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.83 e Å3
3744 reflectionsΔρmin = 0.32 e Å3
280 parameters
Special details top

Experimental. 180 frames, detector distance = 100 mm

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)
C10.52543 (13)0.3349 (2)0.4226 (2)0.0519 (5)
C20.48686 (16)0.2193 (3)0.4415 (3)0.0682 (7)
H20.50410.17360.51150.082*
C30.42448 (17)0.1724 (3)0.3592 (3)0.0748 (8)
C40.39987 (16)0.2401 (3)0.2573 (3)0.0801 (9)
H40.35710.20890.20060.096*
C50.43803 (17)0.3562 (4)0.2363 (3)0.0793 (9)
H50.42090.40080.16560.095*
C60.50125 (15)0.4050 (3)0.3205 (2)0.0623 (6)
H60.52640.48250.30810.075*
C70.69341 (12)0.49355 (19)0.59813 (17)0.0418 (4)
C80.70470 (13)0.4220 (2)0.70539 (19)0.0479 (5)
H80.67380.34810.71040.058*
C90.75977 (13)0.4594 (2)0.80069 (17)0.0454 (5)
C100.80727 (11)0.57554 (17)0.79880 (16)0.0380 (4)
C110.79952 (12)0.64124 (17)0.68721 (16)0.0370 (4)
C120.74184 (12)0.59894 (19)0.58899 (17)0.0423 (4)
H120.73660.64320.51690.051*
C130.84989 (12)0.74918 (17)0.67492 (16)0.0387 (4)
H130.84480.79020.60130.046*
C140.96009 (12)0.89996 (16)0.76805 (15)0.0361 (4)
C151.04588 (12)0.85128 (18)0.82383 (17)0.0415 (4)
H15A1.06860.79930.76590.050*
H15B1.08250.92360.84440.050*
C160.92688 (13)0.99893 (17)0.84776 (16)0.0416 (4)
H16A0.87221.02690.81080.050*
H16B0.92240.96110.92470.050*
C170.96765 (13)0.95486 (18)0.64533 (16)0.0415 (4)
H17A1.01841.00400.65160.050*
H17B0.97140.88490.59020.050*
C18A0.7450 (17)0.268 (2)0.9174 (13)0.094 (4)0.64 (7)
H18A0.76160.23700.99750.141*0.64 (7)
H18B0.76670.21250.86230.141*0.64 (7)
H18C0.68570.26930.89900.141*0.64 (7)
C18B0.725 (2)0.298 (4)0.9220 (17)0.081 (6)0.36 (7)
H18D0.74130.26060.99970.121*0.36 (7)
H18E0.72860.23430.86170.121*0.36 (7)
H18F0.66950.32880.91470.121*0.36 (7)
C190.3212 (2)0.0104 (4)0.3150 (4)0.1198 (15)
H19A0.27450.06410.32110.180*
H19B0.30980.07530.33810.180*
H19C0.33150.01040.23390.180*
N10.58852 (11)0.36940 (18)0.51846 (16)0.0505 (4)
N20.63259 (11)0.46281 (16)0.49844 (15)0.0462 (4)
N30.90261 (10)0.79222 (14)0.76302 (14)0.0372 (4)
O10.39043 (17)0.0567 (3)0.3900 (2)0.1122 (9)
O20.77720 (12)0.39743 (16)0.90751 (15)0.0679 (5)
O30.85535 (9)0.61238 (13)0.89346 (11)0.0445 (4)
O41.04182 (10)0.77718 (13)0.92855 (12)0.0459 (4)
O50.98120 (11)1.10454 (13)0.86388 (13)0.0543 (4)
O60.90017 (10)1.03429 (13)0.59828 (12)0.0483 (4)
H330.9020 (14)0.751 (2)0.828 (2)0.049 (6)*
H441.0605 (16)0.7055 (19)0.919 (2)0.070 (8)*
H550.9770 (17)1.144 (2)0.9268 (19)0.072 (8)*
H660.8772 (16)1.003 (3)0.5358 (19)0.070 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0416 (11)0.0629 (14)0.0513 (12)0.0114 (10)0.0075 (9)0.0190 (10)
C20.0619 (15)0.0732 (16)0.0691 (15)0.0238 (13)0.0099 (12)0.0196 (13)
C30.0614 (15)0.0865 (19)0.0757 (18)0.0238 (15)0.0090 (14)0.0278 (16)
C40.0463 (13)0.099 (2)0.091 (2)0.0131 (14)0.0005 (13)0.0468 (18)
C50.0619 (16)0.113 (2)0.0592 (15)0.0141 (17)0.0016 (12)0.0168 (15)
C60.0509 (13)0.0771 (16)0.0573 (13)0.0010 (12)0.0039 (11)0.0133 (12)
C70.0417 (10)0.0415 (10)0.0405 (10)0.0043 (8)0.0009 (8)0.0045 (8)
C80.0480 (11)0.0414 (10)0.0527 (12)0.0118 (9)0.0027 (9)0.0007 (9)
C90.0467 (11)0.0434 (10)0.0439 (10)0.0076 (9)0.0009 (9)0.0083 (8)
C100.0399 (10)0.0355 (9)0.0373 (9)0.0010 (8)0.0026 (8)0.0005 (7)
C110.0416 (10)0.0316 (8)0.0363 (9)0.0024 (8)0.0014 (8)0.0009 (7)
C120.0496 (11)0.0402 (10)0.0353 (9)0.0041 (8)0.0008 (8)0.0002 (8)
C130.0489 (11)0.0324 (9)0.0333 (9)0.0022 (8)0.0024 (8)0.0003 (7)
C140.0461 (10)0.0282 (8)0.0330 (8)0.0047 (7)0.0027 (7)0.0007 (7)
C150.0462 (11)0.0354 (9)0.0412 (9)0.0037 (8)0.0020 (8)0.0010 (8)
C160.0564 (12)0.0324 (9)0.0350 (9)0.0014 (8)0.0047 (8)0.0012 (7)
C170.0534 (11)0.0355 (9)0.0351 (9)0.0057 (8)0.0055 (8)0.0014 (7)
C18A0.092 (8)0.058 (7)0.118 (8)0.037 (6)0.023 (4)0.044 (4)
C18B0.122 (14)0.055 (10)0.054 (8)0.021 (9)0.020 (6)0.041 (5)
C190.081 (2)0.133 (3)0.146 (4)0.050 (2)0.018 (2)0.049 (3)
N10.0474 (10)0.0517 (10)0.0511 (10)0.0107 (8)0.0041 (8)0.0117 (8)
N20.0455 (9)0.0452 (9)0.0463 (9)0.0083 (8)0.0028 (7)0.0094 (7)
N30.0469 (9)0.0308 (8)0.0324 (8)0.0044 (7)0.0017 (7)0.0013 (6)
O10.1119 (18)0.1044 (18)0.1134 (19)0.0588 (16)0.0033 (15)0.0215 (14)
O20.0788 (11)0.0611 (10)0.0564 (9)0.0313 (9)0.0118 (8)0.0256 (8)
O30.0502 (8)0.0441 (8)0.0364 (7)0.0094 (6)0.0021 (6)0.0035 (6)
O40.0633 (9)0.0330 (7)0.0384 (7)0.0060 (7)0.0009 (6)0.0010 (6)
O50.0830 (11)0.0341 (7)0.0461 (8)0.0134 (7)0.0113 (8)0.0103 (6)
O60.0701 (10)0.0361 (7)0.0342 (7)0.0017 (7)0.0058 (7)0.0013 (6)
Geometric parameters (Å, º) top
C1—C61.372 (4)C14—C161.529 (3)
C1—C21.396 (3)C14—C151.532 (3)
C1—N11.420 (3)C15—O41.427 (2)
C2—C31.359 (4)C15—H15A0.9700
C2—H20.9300C15—H15B0.9700
C3—C41.359 (5)C16—O51.411 (2)
C3—O11.399 (4)C16—H16A0.9700
C4—C51.403 (5)C16—H16B0.9700
C4—H40.9300C17—O61.416 (3)
C5—C61.387 (4)C17—H17A0.9700
C5—H50.9300C17—H17B0.9700
C6—H60.9300C18A—O21.463 (16)
C7—C121.371 (3)C18A—H18A0.9600
C7—C81.413 (3)C18A—H18B0.9600
C7—N21.418 (3)C18A—H18C0.9600
C8—C91.349 (3)C18B—O21.37 (2)
C8—H80.9300C18B—H18D0.9600
C9—O21.362 (2)C18B—H18E0.9600
C9—C101.443 (3)C18B—H18F0.9600
C10—O31.284 (2)C19—O11.391 (4)
C10—C111.426 (3)C19—H19A0.9600
C11—C121.410 (3)C19—H19B0.9600
C11—C131.417 (3)C19—H19C0.9600
C12—H120.9300N1—N21.256 (2)
C13—N31.291 (2)N3—H330.86 (2)
C13—H130.9300O4—H440.824 (17)
C14—N31.463 (2)O5—H550.836 (17)
C14—C171.527 (2)O6—H660.815 (17)
C6—C1—C2121.0 (2)O4—C15—H15A109.4
C6—C1—N1125.8 (2)C14—C15—H15A109.4
C2—C1—N1113.2 (2)O4—C15—H15B109.4
C3—C2—C1121.0 (3)C14—C15—H15B109.4
C3—C2—H2119.5H15A—C15—H15B108.0
C1—C2—H2119.5O5—C16—C14109.24 (16)
C4—C3—C2118.9 (3)O5—C16—H16A109.8
C4—C3—O1125.8 (3)C14—C16—H16A109.8
C2—C3—O1115.2 (3)O5—C16—H16B109.8
C3—C4—C5120.9 (2)C14—C16—H16B109.8
C3—C4—H4119.5H16A—C16—H16B108.3
C5—C4—H4119.5O6—C17—C14113.02 (16)
C6—C5—C4120.3 (3)O6—C17—H17A109.0
C6—C5—H5119.8C14—C17—H17A109.0
C4—C5—H5119.8O6—C17—H17B109.0
C1—C6—C5117.8 (3)C14—C17—H17B109.0
C1—C6—H6121.1H17A—C17—H17B107.8
C5—C6—H6121.1O2—C18A—H18A109.5
C12—C7—C8119.48 (18)O2—C18A—H18B109.5
C12—C7—N2117.59 (17)H18A—C18A—H18B109.5
C8—C7—N2122.92 (18)O2—C18A—H18C109.5
C9—C8—C7120.88 (19)H18A—C18A—H18C109.5
C9—C8—H8119.6H18B—C18A—H18C109.5
C7—C8—H8119.6O2—C18B—H18D109.5
C8—C9—O2126.24 (18)O2—C18B—H18E109.5
C8—C9—C10121.66 (18)H18D—C18B—H18E109.5
O2—C9—C10112.10 (17)O2—C18B—H18F109.5
O3—C10—C11123.48 (16)H18D—C18B—H18F109.5
O3—C10—C9119.99 (16)H18E—C18B—H18F109.5
C11—C10—C9116.49 (16)O1—C19—H19A109.5
C12—C11—C13119.93 (17)O1—C19—H19B109.5
C12—C11—C10120.11 (17)H19A—C19—H19B109.5
C13—C11—C10119.96 (16)O1—C19—H19C109.5
C7—C12—C11121.00 (17)H19A—C19—H19C109.5
C7—C12—H12119.5H19B—C19—H19C109.5
C11—C12—H12119.5N2—N1—C1115.35 (19)
N3—C13—C11121.94 (17)N1—N2—C7112.53 (17)
N3—C13—H13119.0C13—N3—C14130.15 (16)
C11—C13—H13119.0C13—N3—H33113.0 (15)
N3—C14—C17113.51 (15)C14—N3—H33116.9 (16)
N3—C14—C16104.87 (15)C19—O1—C3117.8 (3)
C17—C14—C16111.80 (15)C9—O2—C18B114.9 (9)
N3—C14—C15107.59 (14)C9—O2—C18A118.8 (6)
C17—C14—C15107.33 (15)C15—O4—H44108.2 (19)
C16—C14—C15111.73 (15)C16—O5—H55111 (2)
O4—C15—C14111.20 (16)C17—O6—H66108 (2)
C6—C1—C2—C30.3 (4)C12—C11—C13—N3178.97 (18)
N1—C1—C2—C3179.4 (2)C10—C11—C13—N31.1 (3)
C1—C2—C3—C40.0 (4)N3—C14—C15—O446.68 (19)
C1—C2—C3—O1179.1 (2)C17—C14—C15—O4169.18 (15)
C2—C3—C4—C50.2 (4)C16—C14—C15—O467.92 (19)
O1—C3—C4—C5179.3 (3)N3—C14—C16—O5176.68 (15)
C3—C4—C5—C60.8 (4)C17—C14—C16—O559.9 (2)
C2—C1—C6—C50.8 (4)C15—C14—C16—O560.41 (19)
N1—C1—C6—C5179.8 (2)N3—C14—C17—O677.8 (2)
C4—C5—C6—C11.0 (4)C16—C14—C17—O640.6 (2)
C12—C7—C8—C93.1 (3)C15—C14—C17—O6163.42 (15)
N2—C7—C8—C9175.8 (2)C6—C1—N1—N210.5 (3)
C7—C8—C9—O2178.6 (2)C2—C1—N1—N2170.4 (2)
C7—C8—C9—C102.1 (3)C1—N1—N2—C7179.06 (17)
C8—C9—C10—O3175.70 (19)C12—C7—N2—N1176.11 (18)
O2—C9—C10—O33.7 (3)C8—C7—N2—N12.8 (3)
C8—C9—C10—C116.5 (3)C11—C13—N3—C14179.28 (17)
O2—C9—C10—C11174.16 (18)C17—C14—N3—C1310.9 (3)
O3—C10—C11—C12176.37 (18)C16—C14—N3—C13111.4 (2)
C9—C10—C11—C125.9 (3)C15—C14—N3—C13129.5 (2)
O3—C10—C11—C133.7 (3)C4—C3—O1—C195.2 (5)
C9—C10—C11—C13174.08 (17)C2—C3—O1—C19173.8 (3)
C8—C7—C12—C113.6 (3)C8—C9—O2—C18B9 (2)
N2—C7—C12—C11175.32 (18)C10—C9—O2—C18B170 (2)
C13—C11—C12—C7178.93 (18)C8—C9—O2—C18A10.9 (16)
C10—C11—C12—C71.0 (3)C10—C9—O2—C18A169.8 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.86 (2)1.84 (2)2.584 (2)144 (2)
O4—H44···O6i0.82 (2)1.92 (2)2.744 (2)177 (3)
O5—H55···O4ii0.84 (2)1.90 (2)2.734 (2)174 (3)
O6—H66···O3iii0.82 (2)2.00 (2)2.7792 (19)160 (3)
O6—H66···O2iii0.82 (2)2.26 (3)2.800 (2)124 (2)
C15—H15B···G1iv0.93 (1)3.05)3.861 (2)142 (1)
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+2, y+2, z+2; (iii) x, y+3/2, z1/2; (iv) x, y1/2, z+1/2.
(III) (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxy- 4-(4-methoxyphenyldiazenyl)cyclohexa-2,4-dienone top
Crystal data top
C19H23N3O6F(000) = 824
Mr = 389.40Dx = 1.369 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 17273 reflections
a = 16.9333 (9) Åθ = 1.9–28.8°
b = 10.7124 (6) ŵ = 0.10 mm1
c = 10.5476 (6) ÅT = 296 K
β = 98.966 (4)°Plate, red
V = 1889.92 (18) Å30.35 × 0.23 × 0.09 mm
Z = 4
Data collection top
STOE IPD-II
diffractometer
3714 independent reflections
Radiation source: fine-focus sealed tube2438 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.116
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 2020
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.973, Tmax = 0.993l = 1212
17746 measured reflections
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)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0684P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
3714 reflectionsΔρmax = 0.23 e Å3
311 parametersΔρmin = 0.18 e Å3
42 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
Crystal data top
C19H23N3O6V = 1889.92 (18) Å3
Mr = 389.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.9333 (9) ŵ = 0.10 mm1
b = 10.7124 (6) ÅT = 296 K
c = 10.5476 (6) Å0.35 × 0.23 × 0.09 mm
β = 98.966 (4)°
Data collection top
STOE IPD-II
diffractometer
3714 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
2438 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.993Rint = 0.116
17746 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05042 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.23 e Å3
3714 reflectionsΔρmin = 0.18 e Å3
311 parameters
Special details top

Experimental. 243 frames, detector distance = 100 mm

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)
C10.47825 (17)0.4219 (2)0.6766 (3)0.0612 (7)
C2A0.5108 (8)0.3170 (11)0.7251 (11)0.137 (2)0.409 (7)
H2A0.49550.24300.68220.164*0.409 (7)
C2B0.5420 (3)0.3368 (6)0.6687 (5)0.0555 (14)0.591 (7)
H2B0.54100.28480.59790.067*0.591 (7)
C3A0.5666 (9)0.3103 (10)0.8364 (13)0.1364 (6)0.409 (7)
H3A0.57780.23470.87880.164*0.409 (7)
C3B0.6052 (3)0.3334 (5)0.7687 (5)0.0588 (14)0.591 (7)
H3B0.64830.28040.76530.071*0.591 (7)
C40.6036 (2)0.4146 (3)0.8809 (3)0.0800 (10)
C5A0.5640 (6)0.5219 (10)0.8497 (8)0.067 (2)0.591 (7)
H5A0.57760.59330.89850.081*0.591 (7)
C5B0.5440 (8)0.4927 (14)0.8831 (12)0.062 (3)0.409 (7)
H5B0.54410.54680.95210.075*0.409 (7)
C6A0.5031 (5)0.5271 (8)0.7457 (8)0.067 (2)0.591 (7)
H6A0.47860.60320.72220.080*0.591 (7)
C6B0.4811 (8)0.4942 (11)0.7822 (10)0.060 (3)0.409 (7)
H6B0.43850.54780.78730.073*0.409 (7)
C70.30538 (15)0.5163 (2)0.46511 (19)0.0447 (5)
C80.29236 (15)0.4275 (2)0.3637 (2)0.0462 (6)
H80.32240.35440.36890.055*
C90.23633 (15)0.44917 (18)0.25949 (18)0.0403 (5)
C100.19049 (13)0.56275 (18)0.24400 (17)0.0355 (5)
C110.20056 (13)0.64624 (17)0.35168 (18)0.0371 (5)
C120.25884 (15)0.6205 (2)0.45999 (19)0.0456 (6)
H120.26550.67570.52890.055*
C130.15416 (13)0.75538 (18)0.35053 (18)0.0373 (5)
H130.16260.80730.42210.045*
C140.04710 (13)0.89617 (16)0.24302 (16)0.0327 (5)
C150.03672 (13)0.85092 (18)0.18749 (17)0.0366 (5)
H15A0.05910.80500.25270.044*
H15B0.07080.92240.16260.044*
C160.08007 (14)0.98723 (17)0.15268 (17)0.0385 (5)
H16A0.13471.00950.18700.046*
H16B0.07950.94910.06910.046*
C170.04120 (14)0.95798 (17)0.37162 (16)0.0350 (5)
H17A0.00801.00560.36340.042*
H17B0.03850.89350.43530.042*
C180.6817 (2)0.4947 (5)1.0700 (3)0.1046 (13)
H18A0.70790.46881.15320.157*0.50
H18B0.64130.55541.07990.157*0.50
H18C0.72010.53101.02310.157*0.50
H18D0.67170.56801.01760.157*0.50
H18E0.73830.48141.09090.157*0.50
H18F0.65940.50581.14760.157*0.50
C190.2502 (2)0.2484 (3)0.1693 (3)0.0892 (12)
H19A0.23200.20190.09250.134*
H19B0.23390.20670.24150.134*
H19C0.30750.25440.18160.134*
N10.41502 (15)0.42043 (19)0.5698 (2)0.0607 (6)
N20.36663 (13)0.50856 (18)0.57222 (18)0.0521 (5)
N30.10037 (11)0.78718 (14)0.25490 (15)0.0347 (4)
O1A0.6473 (7)0.3947 (13)1.0053 (11)0.096 (4)0.409 (7)
O1B0.6754 (4)0.4066 (9)0.9636 (7)0.0733 (17)0.591 (7)
O20.21672 (12)0.36987 (14)0.15796 (15)0.0579 (5)
O30.14223 (10)0.58546 (12)0.14174 (12)0.0414 (4)
O40.03509 (11)0.77273 (13)0.07885 (12)0.0418 (4)
O50.03106 (13)1.09466 (13)0.14145 (15)0.0539 (5)
O60.10637 (10)1.03845 (12)0.41583 (12)0.0415 (4)
H330.0970 (16)0.732 (2)0.188 (2)0.056 (7)*
H440.0647 (17)0.711 (2)0.085 (3)0.074 (10)*
H550.035 (2)1.136 (3)0.078 (3)0.114 (14)*
H660.1294 (15)1.017 (2)0.4899 (18)0.055 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0573 (18)0.0550 (14)0.0635 (15)0.0142 (13)0.0151 (13)0.0064 (11)
C2A0.1500.071 (7)0.1500.044 (8)0.101 (6)0.037 (7)
C2B0.047 (3)0.048 (3)0.070 (3)0.008 (2)0.004 (2)0.004 (2)
C3A0.1500.0700.1500.039 (6)0.099 (6)0.000 (7)
C3B0.041 (3)0.053 (3)0.078 (3)0.009 (2)0.006 (2)0.007 (2)
C40.072 (2)0.0658 (18)0.087 (2)0.0112 (16)0.0337 (17)0.0044 (15)
C5A0.057 (6)0.087 (5)0.053 (5)0.009 (4)0.003 (3)0.008 (4)
C5B0.042 (6)0.104 (9)0.040 (5)0.023 (6)0.004 (4)0.004 (4)
C6A0.062 (5)0.068 (4)0.064 (5)0.014 (4)0.012 (3)0.006 (3)
C6B0.052 (6)0.082 (8)0.046 (5)0.025 (5)0.002 (4)0.006 (4)
C70.0486 (14)0.0419 (11)0.0390 (10)0.0070 (10)0.0075 (10)0.0019 (8)
C80.0500 (15)0.0373 (11)0.0488 (12)0.0090 (10)0.0007 (11)0.0008 (9)
C90.0485 (14)0.0329 (10)0.0378 (10)0.0025 (9)0.0019 (9)0.0062 (8)
C100.0379 (12)0.0327 (10)0.0336 (9)0.0005 (9)0.0018 (9)0.0001 (7)
C110.0434 (13)0.0309 (9)0.0338 (9)0.0037 (9)0.0039 (9)0.0024 (7)
C120.0541 (15)0.0407 (11)0.0369 (10)0.0059 (10)0.0084 (10)0.0041 (8)
C130.0432 (13)0.0325 (10)0.0328 (9)0.0016 (9)0.0045 (9)0.0032 (7)
C140.0452 (13)0.0262 (9)0.0248 (8)0.0061 (8)0.0009 (8)0.0005 (7)
C150.0453 (13)0.0311 (9)0.0313 (9)0.0027 (9)0.0006 (9)0.0006 (7)
C160.0535 (14)0.0332 (10)0.0275 (9)0.0001 (9)0.0022 (9)0.0013 (7)
C170.0462 (13)0.0309 (9)0.0266 (8)0.0042 (9)0.0021 (8)0.0002 (7)
C180.074 (2)0.156 (4)0.073 (2)0.018 (3)0.0236 (18)0.018 (2)
C190.118 (3)0.0473 (15)0.092 (2)0.0254 (17)0.016 (2)0.0311 (15)
N10.0623 (15)0.0518 (12)0.0608 (12)0.0145 (11)0.0129 (11)0.0036 (9)
N20.0528 (13)0.0497 (11)0.0479 (10)0.0122 (10)0.0102 (9)0.0042 (8)
N30.0449 (11)0.0283 (8)0.0288 (8)0.0039 (7)0.0006 (7)0.0021 (6)
O1A0.088 (9)0.094 (5)0.086 (7)0.013 (6)0.049 (5)0.007 (5)
O1B0.048 (3)0.079 (3)0.084 (4)0.010 (3)0.019 (2)0.007 (3)
O20.0773 (14)0.0408 (8)0.0499 (9)0.0161 (8)0.0084 (8)0.0161 (7)
O30.0488 (10)0.0393 (7)0.0318 (7)0.0061 (7)0.0073 (6)0.0055 (5)
O40.0608 (11)0.0299 (7)0.0314 (7)0.0069 (7)0.0031 (7)0.0011 (5)
O50.0885 (14)0.0326 (8)0.0411 (8)0.0127 (8)0.0114 (8)0.0100 (6)
O60.0592 (11)0.0341 (7)0.0266 (6)0.0020 (7)0.0070 (7)0.0005 (5)
Geometric parameters (Å, º) top
C1—C2A1.319 (11)C12—H120.9300
C1—C6B1.352 (13)C13—N31.295 (3)
C1—C6A1.372 (9)C13—H130.9300
C1—C2B1.425 (7)C14—N31.469 (2)
C1—N11.428 (3)C14—C171.527 (2)
C2A—C3A1.389 (13)C14—C151.528 (3)
C2A—H2A0.9300C14—C161.529 (3)
C2B—C3B1.381 (7)C15—O41.423 (2)
C2B—H2B0.9300C15—H15A0.9700
C3A—C41.331 (12)C15—H15B0.9700
C3A—H3A0.9300C16—O51.413 (3)
C3B—C41.472 (6)C16—H16A0.9700
C3B—H3B0.9300C16—H16B0.9700
C4—C5B1.314 (15)C17—O61.420 (3)
C4—C5A1.346 (11)C17—H17A0.9700
C4—O1B1.385 (9)C17—H17B0.9700
C4—O1A1.419 (11)C18—O1A1.353 (14)
C5A—C6A1.385 (14)C18—O1B1.458 (10)
C5A—H5A0.9300C18—H18A0.9600
C5B—C6B1.38 (2)C18—H18B0.9600
C5B—H5B0.9300C18—H18C0.9600
C6A—H6A0.9300C18—H18D0.9600
C6B—H6B0.9300C18—H18E0.9600
C7—C121.363 (3)C18—H18F0.9600
C7—N21.412 (3)C19—O21.417 (3)
C7—C81.422 (3)C19—H19A0.9600
C8—C91.356 (3)C19—H19B0.9600
C8—H80.9300C19—H19C0.9600
C9—O21.367 (2)N1—N21.253 (3)
C9—C101.439 (3)N3—H330.92 (3)
C10—O31.271 (2)O4—H440.837 (18)
C10—C111.435 (3)O5—H550.815 (19)
C11—C131.408 (3)O6—H660.850 (17)
C11—C121.416 (3)
C2A—C1—C6B102.1 (7)C17—C14—C15107.03 (18)
C2A—C1—C6A114.8 (6)N3—C14—C16106.34 (16)
C6B—C1—C2B119.0 (6)C17—C14—C16110.97 (15)
C6A—C1—C2B112.6 (5)C15—C14—C16111.79 (15)
C2A—C1—N1120.9 (5)O4—C15—C14111.23 (18)
C6B—C1—N1125.6 (6)O4—C15—H15A109.4
C6A—C1—N1123.9 (4)C14—C15—H15A109.4
C2B—C1—N1115.3 (3)O4—C15—H15B109.4
C1—C2A—C3A124.1 (10)C14—C15—H15B109.4
C1—C2A—H2A118.0H15A—C15—H15B108.0
C3A—C2A—H2A118.0O5—C16—C14107.77 (17)
C3B—C2B—C1118.4 (5)O5—C16—H16A110.2
C3B—C2B—H2B120.8C14—C16—H16A110.2
C1—C2B—H2B120.8O5—C16—H16B110.2
C4—C3A—C2A118.4 (9)C14—C16—H16B110.2
C4—C3A—H3A120.8H16A—C16—H16B108.5
C2A—C3A—H3A120.8O6—C17—C14113.57 (17)
C2B—C3B—C4119.3 (5)O6—C17—H17A108.9
C2B—C3B—H3B120.3C14—C17—H17A108.9
C4—C3B—H3B120.3O6—C17—H17B108.9
C5B—C4—C3A102.7 (10)C14—C17—H17B108.9
C3A—C4—C5A116.2 (6)H17A—C17—H17B107.7
C5B—C4—O1B129.1 (8)O1A—C18—H18A109.5
C3A—C4—O1B119.3 (6)O1B—C18—H18A118.9
C5A—C4—O1B124.2 (6)O1A—C18—H18B109.5
C5B—C4—O1A111.8 (9)O1B—C18—H18B123.6
C3A—C4—O1A110.4 (8)H18A—C18—H18B109.5
C5A—C4—O1A121.5 (8)O1A—C18—H18C109.5
C5B—C4—C3B120.0 (7)O1B—C18—H18C80.7
C5A—C4—C3B112.3 (5)H18A—C18—H18C109.5
O1B—C4—C3B110.2 (5)H18B—C18—H18C109.5
O1A—C4—C3B125.6 (6)O1A—C18—H18D109.5
C4—C5A—C6A120.6 (9)O1B—C18—H18D95.7
C4—C5A—H5A119.7H18A—C18—H18D141.1
C6A—C5A—H5A119.7H18B—C18—H18D56.3
C4—C5B—C6B119.7 (13)H18C—C18—H18D56.3
C4—C5B—H5B120.2O1A—C18—H18E109.5
C6B—C5B—H5B120.2O1B—C18—H18E91.7
C1—C6A—C5A121.1 (8)H18A—C18—H18E56.3
C1—C6A—H6A119.5H18B—C18—H18E141.1
C5A—C6A—H6A119.5H18C—C18—H18E56.3
C1—C6B—C5B123.5 (11)H18D—C18—H18E109.5
C1—C6B—H6B118.3O1A—C18—H18F109.5
C5B—C6B—H6B118.3O1B—C18—H18F138.2
C12—C7—N2115.33 (19)H18A—C18—H18F56.3
C12—C7—C8119.8 (2)H18B—C18—H18F56.3
N2—C7—C8124.8 (2)H18C—C18—H18F141.1
C9—C8—C7120.1 (2)H18D—C18—H18F109.5
C9—C8—H8119.9H18E—C18—H18F109.5
C7—C8—H8119.9O2—C19—H19A109.5
C8—C9—O2125.7 (2)O2—C19—H19B109.5
C8—C9—C10122.27 (18)H19A—C19—H19B109.5
O2—C9—C10112.07 (18)O2—C19—H19C109.5
O3—C10—C11122.26 (18)H19A—C19—H19C109.5
O3—C10—C9121.49 (17)H19B—C19—H19C109.5
C11—C10—C9116.22 (17)N2—N1—C1112.8 (2)
C13—C11—C12119.13 (17)N1—N2—C7115.4 (2)
C13—C11—C10120.90 (18)C13—N3—C14128.58 (16)
C12—C11—C10119.96 (18)C13—N3—H33112.5 (17)
C7—C12—C11121.18 (19)C14—N3—H33118.9 (17)
C7—C12—H12119.4C18—O1A—C4118.0 (10)
C11—C12—H12119.4C4—O1B—C18113.3 (6)
N3—C13—C11123.31 (18)C9—O2—C19117.35 (19)
N3—C13—H13118.3C15—O4—H44109 (2)
C11—C13—H13118.3C16—O5—H55113 (3)
N3—C14—C17113.17 (15)C17—O6—H66110.9 (18)
N3—C14—C15107.58 (15)
C6B—C1—C2A—C3A27.9 (15)C8—C9—C10—C117.0 (3)
C6A—C1—C2A—C3A0.6 (16)O2—C9—C10—C11173.55 (19)
C2B—C1—C2A—C3A94.7 (17)O3—C10—C11—C132.9 (3)
N1—C1—C2A—C3A173.2 (11)C9—C10—C11—C13175.1 (2)
C2A—C1—C2B—C3B71.7 (9)O3—C10—C11—C12175.9 (2)
C6B—C1—C2B—C3B1.3 (8)C9—C10—C11—C126.0 (3)
C6A—C1—C2B—C3B29.9 (6)N2—C7—C12—C11173.6 (2)
N1—C1—C2B—C3B179.9 (4)C8—C7—C12—C113.8 (4)
C1—C2A—C3A—C416 (2)C13—C11—C12—C7179.7 (2)
C1—C2B—C3B—C41.7 (7)C10—C11—C12—C70.9 (4)
C2A—C3A—C4—C5B50.5 (15)C12—C11—C13—N3179.0 (2)
C2A—C3A—C4—C5A26.2 (17)C10—C11—C13—N30.2 (3)
C2A—C3A—C4—O1B159.3 (10)N3—C14—C15—O447.77 (19)
C2A—C3A—C4—O1A169.9 (11)C17—C14—C15—O4169.68 (14)
C2A—C3A—C4—C3B69.7 (12)C16—C14—C15—O468.62 (19)
C2B—C3B—C4—C5B2.6 (9)N3—C14—C16—O5178.70 (16)
C2B—C3B—C4—C3A74.4 (7)C17—C14—C16—O555.2 (2)
C2B—C3B—C4—C5A31.0 (8)C15—C14—C16—O564.2 (2)
C2B—C3B—C4—O1B173.9 (5)N3—C14—C17—O680.6 (2)
C2B—C3B—C4—O1A157.7 (7)C15—C14—C17—O6161.11 (15)
C5B—C4—C5A—C6A85 (3)C16—C14—C17—O638.9 (2)
C3A—C4—C5A—C6A20.7 (13)C2A—C1—N1—N2147.9 (8)
O1B—C4—C5A—C6A165.1 (7)C6B—C1—N1—N211.1 (7)
O1A—C4—C5A—C6A160.1 (8)C6A—C1—N1—N224.0 (6)
C3B—C4—C5A—C6A28.2 (9)C2B—C1—N1—N2170.2 (3)
C3A—C4—C5B—C6B41.5 (13)C1—N1—N2—C7176.4 (2)
C5A—C4—C5B—C6B83 (2)C12—C7—N2—N1172.2 (2)
O1B—C4—C5B—C6B172.4 (8)C8—C7—N2—N15.0 (4)
O1A—C4—C5B—C6B159.9 (10)C11—C13—N3—C14178.5 (2)
C3B—C4—C5B—C6B2.9 (13)C17—C14—N3—C1316.8 (3)
C2A—C1—C6A—C5A6.6 (11)C15—C14—N3—C13134.9 (2)
C6B—C1—C6A—C5A75.4 (15)C16—C14—N3—C13105.2 (2)
C2B—C1—C6A—C5A34.1 (8)O1B—C18—O1A—C466.7 (14)
N1—C1—C6A—C5A178.9 (5)C5B—C4—O1A—C1859.5 (13)
C4—C5A—C6A—C14.1 (11)C3A—C4—O1A—C18173.2 (10)
C2A—C1—C6B—C5B37.3 (13)C5A—C4—O1A—C1831.8 (14)
C6A—C1—C6B—C5B82.7 (19)O1B—C4—O1A—C1873.0 (17)
C2B—C1—C6B—C5B1.7 (13)C3B—C4—O1A—C18138.8 (8)
N1—C1—C6B—C5B179.7 (8)C5B—C4—O1B—C183.3 (11)
C4—C5B—C6B—C12.6 (16)C3A—C4—O1B—C18138.1 (10)
C12—C7—C8—C93.0 (4)C5A—C4—O1B—C1836.0 (9)
N2—C7—C8—C9174.1 (2)O1A—C4—O1B—C1858.6 (16)
C7—C8—C9—O2178.0 (2)C3B—C4—O1B—C18173.6 (4)
C7—C8—C9—C102.5 (4)O1A—C18—O1B—C464.8 (14)
C8—C9—C10—O3175.0 (2)C8—C9—O2—C198.4 (4)
O2—C9—C10—O34.5 (3)C10—C9—O2—C19172.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.92 (3)1.84 (3)2.619 (2)141 (2)
O5—H55···O4i0.82 (2)1.92 (2)2.733 (2)174 (4)
O4—H44···O6ii0.84 (2)1.98 (2)2.789 (2)163 (3)
O6—H66···O3iii0.85 (2)1.92 (2)2.7125 (18)154 (2)
O6—H66···O2iii0.85 (2)2.45 (2)3.081 (2)132 (2)
C3—H3···G1iv0.93 (1)3.32 (1)3.463 (7)91 (1)
Symmetry codes: (i) x, y+2, z; (ii) x, y1/2, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y+1, z+1.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC18H19Cl2N3O5C19H23N3O6C19H23N3O6
Mr428.26389.40389.40
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)296296296
a, b, c (Å)16.8445 (15), 10.7259 (5), 11.1126 (9)16.3722 (11), 10.4506 (5), 11.3239 (7)16.9333 (9), 10.7124 (6), 10.5476 (6)
α, β, γ (°)90, 106.037 (7), 9090, 99.180 (5), 9090, 98.966 (4), 90
V3)1929.6 (2)1912.7 (2)1889.92 (18)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.370.100.10
Crystal size (mm)0.78 × 0.33 × 0.050.42 × 0.33 × 0.250.35 × 0.23 × 0.09
Data collection
DiffractometerSTOE IPDS-II
diffractometer
STOE IPDS-II
diffractometer
STOE IPD-II
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Integration
STOE X-RED (Stoe & Cie, 2002)
Integration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.871, 0.9770.970, 0.9820.973, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
10068, 3782, 2715 13464, 3744, 2778 17746, 3714, 2438
Rint0.0560.0400.116
(sin θ/λ)max1)0.6170.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.132, 1.02 0.053, 0.160, 1.06 0.050, 0.135, 0.99
No. of reflections378237443714
No. of parameters269280311
No. of restraints0342
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)0.31, 0.360.83, 0.320.23, 0.18

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) for (I) top
C1—N11.443 (3)C10—O31.279 (3)
C2—Cl11.727 (3)C10—C111.434 (3)
C6—Cl21.732 (3)C11—C121.406 (3)
C7—C121.372 (3)C11—C131.425 (3)
C7—C81.409 (3)C13—N31.284 (3)
C7—N21.417 (3)C14—N31.464 (3)
C8—C91.364 (3)C18—O11.417 (3)
C9—O11.357 (3)N1—N21.243 (3)
C9—C101.434 (3)
C6—C1—N1120.0 (2)O3—C10—C11123.37 (19)
C2—C1—N1122.2 (2)N3—C13—C11122.2 (2)
C8—C7—N2113.35 (19)C15—C14—C17107.13 (18)
O1—C9—C8126.3 (2)C13—N3—C14129.6 (2)
C10—C11—C13—N30.3 (3)C1—N1—N2—C7179.2 (2)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.79 (3)1.90 (3)2.587 (2)144 (3)
O4—H44···O6i0.74 (3)2.04 (3)2.777 (3)174 (3)
O5—H55···O4ii0.80 (4)1.94 (4)2.740 (3)176 (3)
O6—H66···O1iii0.70 (3)2.25 (3)2.802 (2)137 (3)
O6—H66···O3iii0.70 (3)2.28 (3)2.923 (2)153 (3)
C17—H17A···G1iv0.97 (0)2.9471 (0)3.798 (2)147.06 (0)
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+2, y, z+2; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z+1/2.
Selected geometric parameters (Å, º) for (II) top
C1—N11.420 (3)C10—O31.284 (2)
C3—O11.399 (4)C10—C111.426 (3)
C7—C121.371 (3)C11—C121.410 (3)
C7—C81.413 (3)C11—C131.417 (3)
C7—N21.418 (3)C13—N31.291 (2)
C8—C91.349 (3)C14—N31.463 (2)
C9—O21.362 (2)N1—N21.256 (2)
C9—C101.443 (3)
C6—C1—N1125.8 (2)O3—C10—C11123.48 (16)
C2—C1—N1113.2 (2)N3—C13—C11121.94 (17)
C2—C3—O1115.2 (3)C17—C14—C15107.33 (15)
C8—C7—N2122.92 (18)C13—N3—C14130.15 (16)
C8—C9—O2126.24 (18)
C10—C11—C13—N31.1 (3)C1—N1—N2—C7179.06 (17)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.86 (2)1.84 (2)2.584 (2)144 (2)
O4—H44···O6i0.824 (17)1.921 (18)2.744 (2)177 (3)
O5—H55···O4ii0.836 (17)1.901 (18)2.734 (2)174 (3)
O6—H66···O3iii0.815 (17)1.999 (19)2.7792 (19)160 (3)
O6—H66···O2iii0.815 (17)2.26 (3)2.800 (2)124 (2)
C15—H15B···G1iv0.93 (0)3.05210)3.861 (2)141.74 (0)
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+2, y+2, z+2; (iii) x, y+3/2, z1/2; (iv) x, y1/2, z+1/2.
Selected geometric parameters (Å, º) for (III) top
C1—N11.428 (3)C10—C111.435 (3)
C7—C121.363 (3)C11—C131.408 (3)
C7—N21.412 (3)C11—C121.416 (3)
C7—C81.422 (3)C13—N31.295 (3)
C8—C91.356 (3)C14—N31.469 (2)
C9—O21.367 (2)C19—O21.417 (3)
C9—C101.439 (3)N1—N21.253 (3)
C10—O31.271 (2)
C12—C7—N2115.33 (19)O3—C10—C11122.26 (18)
C12—C7—C8119.8 (2)N3—C13—C11123.31 (18)
N2—C7—C8124.8 (2)C17—C14—C15107.03 (18)
C8—C9—O2125.7 (2)C13—N3—C14128.58 (16)
C10—C11—C13—N30.2 (3)C1—N1—N2—C7176.4 (2)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N3—H33···O30.92 (3)1.84 (3)2.619 (2)141 (2)
O5—H55···O4i0.815 (19)1.92 (2)2.733 (2)174 (4)
O4—H44···O6ii0.837 (18)1.98 (2)2.789 (2)163 (3)
O6—H66···O3iii0.850 (17)1.924 (19)2.7125 (18)154 (2)
O6—H66···O2iii0.850 (17)2.45 (2)3.081 (2)132 (2)
C3—H3···G1iv0.93 (0)3.322 (0)3.463 (7)90.82 (0)
Symmetry codes: (i) x, y+2, z; (ii) x, y1/2, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y+1, z+1.
The observed 'π–p' interaction distances (Å) for (I), (II) and (III). top
CompoundCg-Cgi,iidcentroidsdperpendicular
ICg1-Cg1i3,556 (2)3,38
IICg1-Cg2ii3,937 (1)3,57
IIICg1-Cg2ii3,996 (3)3,66
Cg1, Cg2 are the centroid of the C1–C6 and C7–C12 rings, respectively. [Symmetry codes: (i) 1 − x, 1 − y, 2 − z; (ii) 1 − x, 1 − y, 1 − z.]
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds