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In the title compounds, C10H8N2O2, (I), and C12H12N2O2, (II), the two carbonyl groups are oriented with torsion angles of -149.3 (3) and -88.55 (15)°, respectively. The single-bond distances linking the two carbonyl groups are 1.528 (4) and 1.5298 (17) Å, respectively. In (I), the mol­ecules are linked by an elaborate system of N-H...O hydrogen bonds, which form adjacent R22(8) and R42(8) ring motifs to generate a ladder-like construct. Adjacent ladders are further linked by N-H...O hydrogen bonds to build a three-dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N-H...O-linked mol­ecules that follow the 21 screw of the b axis. It is the presence of an elaborate hydrogen-bonding system in the crystal structure of (I) that leads to the different torsion angle for the orientation of the two adjacent carbonyl groups from that in (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112038322/yp3017sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112038322/yp3017Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112038322/yp3017IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112038322/yp3017Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112038322/yp3017IIsup5.cml
Supplementary material

CCDC references: 906580; 906581

Comment top

The title compounds, 2-(1H-indol-3-yl)-2-oxoacetamide, (I), and 2-(1H-indol-3-yl)- N,N-dimethyl-2-oxoacetamide, (II), are synthetic intermediates in the preparation of tryptamine and N,N-dimethyltryptamine, and are prepared by treating indole with oxalyl chloride followed by quenching with aqueous ammonia or dimethylamine, respectively. The products were characterized by spectroscopic analysis and their X-ray crystal structure determinations were carried out to ascertain the conformations of these molecules, especially the orientations of the carbonyl groups, as 1,2-diones have been shown to be potent inhibitors of carboxylesterases (Hyatt et al., 2007). The inhibitory properties of ethane-1,2-diones toward carboxylesterases are such that, when the carbonyl O atoms are cis-coplanar, the compounds demonstrate specificity for human liver carboxylesterase. Conversely, when the dione O atoms are not planar (or are trans-coplanar), the compounds are more potent at human intestinal carboxylesterase inhibition (Hyatt et al., 2007). Thus, the title compounds and their analogs were screened for their inhibition of human carboxylesterases and it was planned to determine their conformations to compare with the observation reported for ethane-1,2-diones.

X-ray crystallography confirmed the molecular structures and atom connectivities of (I) and (II), and selected geometric parameters are listed in Tables 1 and 3. The two carbonyl groups are in a trans orientation, with torsion angle O1—C9—C10—O2 = 149.3 (3)° and O1—C10—C11—O2 = 88.55 (15)°. The deviation from 180° may be due to repulsive interactions between non-bonded electron pairs on atoms O1 and O2. However, in (I) the extensive hydrogen bonding introduces rigidity into the molecule. Since the C9O1 and C10O1 groups are coplanar with the indole nucleus, there is extended conjugation from atom O1 through to the indole ring. This is evident from the shortening of the C8—C9 [1.421 (4) Å] and C1—C10 [1.4380 (17) Å] bond lengths compared with the standard value for a single bond connecting a Car atom to a Csp2 atom [1.470 (15) Å; Allen et al., 1987]. Possibly due to repulsive interactions between non-bonded electron pairs, the C9—C10 and C10—C11 bonds are stretched, resulting in bond lengths of 1.528 (4) and 1.5298 (17) Å, respectively. These are longer than expected, the characteristic value for a Csp2—Csp2 bond being 1.50 Å (Zukerman-Schpector et al., 1994). The C10—N2 [1.323 (4) Å] and C11—N12 [1.3287 (16) Å] bond lengths, and the bond angles around atoms N2 and N12, suggest that the lone pairs of electrons on N2 and N12 undergo delocalization, bestowing double-bond character on the C10—N2 and C11—N12 bonds.

The packing of compounds (I) and (II), as viewed down the c axis [b axis for (II)?], are illustrated in Figs. 2 and 4, respectively. Amides undergo extensive hydrogen bonding, but in (I), in addition to primary amide functionality, there is a hydrogen-bond accepting carbonyl group and a variable glyoxylamide torsion angle. In (I), the molecules are linked by an elaborate system of N—H···O hydrogen bonds [N1—H1···O1i and N2—H2A···O2ii; symmetry codes: (i) x - 1, -y + 3/2, z + 1/2; (ii) -x + 1, -y + 1, -z + 1] which include adjacent R22(8) and R42(8) ring motifs (Bernstein et al., 1995) to form a ladder-like construct. Adjacent ladders are further linked by N—H···O hydrogen bonds [N2—H2B···O2iii; symmetry code: (iii) x + 1, y, z] to build a three-dimensional network. The hydrogen bonding in (II) is far simpler, consisting of helical chains of N—H···O [N3—H3···O2i; symmetry code: (i) -x + 1, y - 1/2, -z + 1/2] linked molecules that follow the 21 screw of the b axis.

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Da Settimo, Primofiore, Da Settimo, Marini, Novellino, Greco, Martini, Giannaccini & Lucacchini (1996); Hyatt et al. (2007); Zukerman-Schpector, Pinto, DaC, Da Silva & Da Silva (1994).

Experimental top

The title compounds were prepared using a previously reported procedure (Da Settimo et al., 1996). Recrystallization from ethyl acetate afforded (I) and (II) as yellow [Both colourless in CIF data tables - please clarify] crystalline products which were suitable for X-ray analysis. Spectroscopic analysis for (I): 1H NMR (300 MHz, DMSO-d6, δ, p.p.m): 7.22–7.25 (m, 2H), 7.49–7.52 (m, 1H), 7.70 (sb, 1H), 8.06 (sb, 1H), 8.19–8.22 (m, 1H), 8.67 (d, 1H), 12.17 (sb, 1H); 13C NMR (75 MHz, DMSO-d6, δ p.p.m.): 111.95, 112.41, 121.10, 122.32, 123.22, 125.98, 136.11, 138.10, 165.80, 182.72. Spectroscopic analysis for (II): 1H NMR (300 MHz, DMSO-d6, δ, p.p.m): 2.93 (s, 3H), 3.01 (s, 3H), 7.23–7.32 (m, 2H), 7.51–7.57 (m, 1H), 8.10 (dd, 1H), 8.14 (s, 1H), 12.17 (sb, 1H); 13C NMR (75 MHz, DMSO-d6, δ, p.p.m.): 33.41, 36.81, 112.52, 112.83, 120.71, 122.38, 123.38, 124.75, 136.73, 136.83, 167.11, 186.44.

Refinement top

H atoms were found in difference Fourier maps and subsequently placed in idealized positions, with C—H = 0.95 (CArH), 0.98 (CMeH) or 0.88 Å (NH2), and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Computing details top

Data collection: APEX2 (Bruker, 2006) for (I); COLLECT (Nonius, 1999) for (II). Cell refinement: APEX2 (Bruker, 2006) for (I); SCALEPACK (Otwinowski & Minor, 1997) for (II). Data reduction: APEX2 (Bruker, 2006) for (I); DENZO-SMN (Otwinowski & Minor, 1997) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and local procedures.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for (I), viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in these interactions have been omitted for clarity. [Added text OK?]
[Figure 3] Fig. 3. A view of the molecule of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 4] Fig. 4. A packing diagram for (II), viewed down the c axis [b axis?]. Dashed lines indicate hydrogen bonds. H atoms not involved in these interactions have been omitted for clarity. [Added text OK?]
(I) 2-(1H-indol-3-yl)-2-oxoacetamide top
Crystal data top
C10H8N2O2F(000) = 392
Mr = 188.18Dx = 1.479 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 8721 reflections
a = 5.1253 (4) Åθ = 4.6–69.0°
b = 19.4363 (14) ŵ = 0.88 mm1
c = 8.4953 (6) ÅT = 90 K
β = 93.251 (3)°Needle, colourless
V = 844.91 (11) Å30.30 × 0.08 × 0.06 mm
Z = 4
Data collection top
Bruker X8 Proteum
diffractometer
1518 independent reflections
Radiation source: fine-focus rotating anode1481 reflections with I > 2σ(I)
Graded multilayer optics monochromatorRint = 0.042
Detector resolution: 18 pixels mm-1θmax = 68.9°, θmin = 4.6°
ϕ and ω scansh = 46
Absorption correction: multi-scan
[SADABS (Bruker, 2006) and XABS2 (Parkin et al., 1995)]
k = 2323
Tmin = 0.744, Tmax = 0.949l = 1010
10887 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)] = 0.058H-atom parameters constrained
wR(F2) = 0.158 w = 1/[σ2(Fo2) + (0.037P)2 + 1.8838P]
where P = (Fo2 + 2Fc2)/3
S = 1.24(Δ/σ)max < 0.001
1518 reflectionsΔρmax = 0.33 e Å3
128 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0033 (9)
Crystal data top
C10H8N2O2V = 844.91 (11) Å3
Mr = 188.18Z = 4
Monoclinic, P21/cCu Kα radiation
a = 5.1253 (4) ŵ = 0.88 mm1
b = 19.4363 (14) ÅT = 90 K
c = 8.4953 (6) Å0.30 × 0.08 × 0.06 mm
β = 93.251 (3)°
Data collection top
Bruker X8 Proteum
diffractometer
1518 independent reflections
Absorption correction: multi-scan
[SADABS (Bruker, 2006) and XABS2 (Parkin et al., 1995)]
1481 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.949Rint = 0.042
10887 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.24Δρmax = 0.33 e Å3
1518 reflectionsΔρmin = 0.33 e Å3
128 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 > 2σ(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
N10.0782 (5)0.77152 (13)0.5558 (3)0.0227 (6)
H10.05290.77660.61730.027*
N20.7272 (5)0.56011 (12)0.4103 (3)0.0219 (6)
H2A0.72420.51630.43620.026*
H2B0.87610.58000.39040.026*
O10.7253 (4)0.68365 (10)0.2684 (2)0.0221 (5)
O20.2916 (4)0.57240 (10)0.4272 (3)0.0231 (5)
C10.1826 (5)0.71168 (15)0.5181 (3)0.0195 (6)
H1A0.12820.66810.55460.023*
C20.2054 (6)0.82452 (15)0.4845 (3)0.0207 (7)
C30.1592 (6)0.89462 (16)0.4918 (4)0.0274 (7)
H30.02540.91290.55240.033*
C40.3164 (6)0.93666 (16)0.4069 (4)0.0297 (8)
H40.28800.98500.40680.036*
C50.5163 (6)0.90938 (16)0.3211 (4)0.0270 (7)
H50.62490.93960.26630.032*
C60.5597 (6)0.83963 (15)0.3143 (4)0.0225 (7)
H60.69580.82180.25480.027*
C70.4006 (5)0.79562 (15)0.3960 (3)0.0186 (6)
C80.3834 (5)0.72223 (15)0.4173 (3)0.0183 (6)
C90.5462 (5)0.67120 (15)0.3542 (3)0.0185 (6)
C100.5078 (5)0.59616 (15)0.4013 (3)0.0192 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0145 (12)0.0325 (14)0.0213 (13)0.0038 (10)0.0036 (10)0.0025 (10)
N20.0094 (11)0.0211 (13)0.0356 (15)0.0008 (9)0.0044 (10)0.0028 (10)
O10.0138 (10)0.0286 (11)0.0247 (11)0.0003 (8)0.0072 (8)0.0019 (8)
O20.0120 (10)0.0239 (11)0.0335 (12)0.0002 (8)0.0037 (8)0.0031 (9)
C10.0142 (14)0.0269 (15)0.0175 (14)0.0009 (11)0.0007 (11)0.0001 (11)
C20.0155 (14)0.0276 (16)0.0186 (15)0.0018 (11)0.0028 (11)0.0035 (11)
C30.0221 (16)0.0295 (17)0.0301 (18)0.0043 (13)0.0037 (13)0.0079 (13)
C40.0274 (17)0.0231 (16)0.0375 (19)0.0039 (13)0.0071 (14)0.0030 (13)
C50.0239 (16)0.0261 (16)0.0302 (18)0.0039 (12)0.0049 (13)0.0023 (13)
C60.0167 (15)0.0268 (16)0.0237 (16)0.0012 (12)0.0016 (12)0.0005 (12)
C70.0130 (13)0.0253 (15)0.0171 (14)0.0009 (11)0.0024 (11)0.0001 (11)
C80.0124 (13)0.0229 (14)0.0195 (14)0.0015 (11)0.0011 (11)0.0003 (11)
C90.0118 (13)0.0238 (15)0.0200 (15)0.0011 (11)0.0009 (11)0.0007 (11)
C100.0128 (14)0.0245 (15)0.0206 (15)0.0003 (11)0.0028 (11)0.0010 (11)
Geometric parameters (Å, º) top
N1—C11.327 (4)C3—C41.379 (5)
N1—C21.378 (4)C3—H30.9500
N1—H10.8800C4—C51.395 (5)
N2—C101.323 (4)C4—H40.9500
N2—H2A0.8800C5—C61.376 (4)
N2—H2B0.8800C5—H50.9500
O1—C91.228 (3)C6—C71.394 (4)
O2—C101.232 (3)C6—H60.9500
C1—C81.391 (4)C7—C81.441 (4)
C1—H1A0.9500C8—C91.421 (4)
C2—C31.385 (4)C9—C101.528 (4)
C2—C71.403 (4)
C1—N1—C2110.0 (2)C6—C5—C4121.5 (3)
C1—N1—H1125.0C6—C5—H5119.3
C2—N1—H1125.0C4—C5—H5119.3
C10—N2—H2A120.0C5—C6—C7118.9 (3)
C10—N2—H2B120.0C5—C6—H6120.6
H2A—N2—H2B120.0C7—C6—H6120.6
N1—C1—C8110.0 (3)C6—C7—C2118.5 (3)
N1—C1—H1A125.0C6—C7—C8135.4 (3)
C8—C1—H1A125.0C2—C7—C8106.2 (2)
N1—C2—C3129.1 (3)C1—C8—C9126.9 (3)
N1—C2—C7107.8 (3)C1—C8—C7106.0 (2)
C3—C2—C7123.1 (3)C9—C8—C7127.0 (3)
C4—C3—C2117.0 (3)O1—C9—C8124.1 (3)
C4—C3—H3121.5O1—C9—C10117.1 (3)
C2—C3—H3121.5C8—C9—C10118.7 (2)
C3—C4—C5121.1 (3)O2—C10—N2124.1 (3)
C3—C4—H4119.5O2—C10—C9122.3 (2)
C5—C4—H4119.5N2—C10—C9113.5 (2)
C2—N1—C1—C80.9 (3)N1—C1—C8—C9178.3 (3)
C1—N1—C2—C3179.8 (3)N1—C1—C8—C71.0 (3)
C1—N1—C2—C70.4 (3)C6—C7—C8—C1178.4 (3)
N1—C2—C3—C4179.5 (3)C2—C7—C8—C10.7 (3)
C7—C2—C3—C40.2 (4)C6—C7—C8—C91.0 (5)
C2—C3—C4—C51.5 (5)C2—C7—C8—C9178.1 (3)
C3—C4—C5—C61.9 (5)C1—C8—C9—O1178.2 (3)
C4—C5—C6—C70.4 (5)C7—C8—C9—O11.3 (5)
C5—C6—C7—C21.2 (4)C1—C8—C9—C101.4 (4)
C5—C6—C7—C8179.8 (3)C7—C8—C9—C10175.5 (3)
N1—C2—C7—C6179.0 (3)O1—C9—C10—O2149.3 (3)
C3—C2—C7—C61.5 (4)C8—C9—C10—O233.7 (4)
N1—C2—C7—C80.2 (3)O1—C9—C10—N230.4 (4)
C3—C2—C7—C8179.2 (3)C8—C9—C10—N2146.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.922.768 (3)160
N2—H2A···O2ii0.882.082.926 (3)161
N2—H2B···O2iii0.882.142.898 (3)144
Symmetry codes: (i) x1, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z.
(II) 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide top
Crystal data top
C12H12N2O2F(000) = 456
Mr = 216.24Dx = 1.313 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2759 reflections
a = 10.1813 (2) Åθ = 1.0–27.5°
b = 6.0048 (1) ŵ = 0.09 mm1
c = 18.0625 (4) ÅT = 90 K
β = 97.7222 (8)°Rod, colourless
V = 1094.27 (4) Å30.65 × 0.25 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2515 independent reflections
Radiation source: fine-focus sealed tube2031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.0°
ω scans at fixed χ = 55°h = 1313
Absorption correction: multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
k = 77
Tmin = 0.943, Tmax = 0.986l = 2323
4780 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.2642P]
where P = (Fo2 + 2Fc2)/3
2515 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C12H12N2O2V = 1094.27 (4) Å3
Mr = 216.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.1813 (2) ŵ = 0.09 mm1
b = 6.0048 (1) ÅT = 90 K
c = 18.0625 (4) Å0.65 × 0.25 × 0.15 mm
β = 97.7222 (8)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2515 independent reflections
Absorption correction: multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
2031 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.986Rint = 0.033
4780 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.06Δρmax = 0.23 e Å3
2515 reflectionsΔρmin = 0.20 e Å3
147 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-value wR and goodness of fit S are based on F2. Conventional R-values R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-values based on F2 are statistically about twice as large as those based on F, and R-values based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.46067 (12)0.5029 (2)0.30948 (7)0.0250 (3)
H10.52630.40040.29830.030*
N10.32928 (10)0.47893 (19)0.28893 (6)0.0262 (3)
H1A0.29140.36760.26250.031*
N20.77326 (10)0.48231 (18)0.42133 (6)0.0253 (3)
O10.63689 (9)0.95880 (17)0.41126 (6)0.0341 (3)
O20.78438 (8)0.65588 (16)0.31061 (5)0.0295 (2)
C20.26301 (12)0.6570 (2)0.31595 (6)0.0229 (3)
C30.12758 (12)0.6955 (2)0.31215 (7)0.0268 (3)
H30.06430.59640.28660.032*
C40.08930 (13)0.8841 (3)0.34723 (7)0.0310 (3)
H40.00240.91500.34630.037*
C50.18277 (13)1.0309 (2)0.38423 (8)0.0317 (3)
H50.15301.16000.40740.038*
C60.31755 (12)0.9925 (2)0.38792 (7)0.0264 (3)
H60.38021.09360.41300.032*
C70.35877 (11)0.8014 (2)0.35382 (6)0.0217 (3)
C80.48596 (11)0.6990 (2)0.34928 (6)0.0218 (3)
C90.61495 (11)0.7791 (2)0.37998 (7)0.0229 (3)
C100.73240 (11)0.6301 (2)0.36848 (7)0.0224 (3)
C110.70814 (13)0.4489 (2)0.48773 (7)0.0294 (3)
H11A0.64630.57160.49230.044*
H11B0.77500.44490.53210.044*
H11C0.65940.30770.48330.044*
C120.88222 (13)0.3315 (2)0.41201 (8)0.0316 (3)
H12A0.90800.35120.36210.047*
H12B0.85380.17740.41790.047*
H12C0.95810.36480.44980.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0232 (6)0.0284 (7)0.0245 (6)0.0007 (5)0.0069 (5)0.0014 (5)
N10.0243 (5)0.0296 (6)0.0250 (5)0.0045 (4)0.0048 (4)0.0056 (4)
N20.0231 (5)0.0277 (6)0.0260 (5)0.0025 (4)0.0068 (4)0.0028 (4)
O10.0264 (5)0.0303 (6)0.0454 (6)0.0025 (4)0.0043 (4)0.0106 (4)
O20.0247 (5)0.0379 (6)0.0275 (5)0.0043 (4)0.0092 (4)0.0068 (4)
C20.0233 (6)0.0271 (7)0.0190 (5)0.0009 (5)0.0048 (4)0.0014 (5)
C30.0213 (6)0.0344 (7)0.0242 (6)0.0032 (5)0.0019 (5)0.0042 (5)
C40.0210 (6)0.0391 (8)0.0332 (7)0.0037 (6)0.0048 (5)0.0050 (6)
C50.0270 (7)0.0311 (8)0.0377 (7)0.0064 (6)0.0073 (5)0.0012 (6)
C60.0245 (6)0.0261 (7)0.0289 (6)0.0002 (5)0.0048 (5)0.0009 (5)
C70.0206 (6)0.0258 (6)0.0193 (5)0.0001 (5)0.0044 (4)0.0033 (5)
C80.0200 (6)0.0251 (6)0.0211 (5)0.0004 (5)0.0058 (4)0.0009 (5)
C90.0233 (6)0.0244 (7)0.0219 (5)0.0004 (5)0.0059 (4)0.0006 (5)
C100.0180 (5)0.0249 (7)0.0243 (6)0.0019 (5)0.0031 (4)0.0005 (5)
C110.0345 (7)0.0311 (7)0.0241 (6)0.0005 (6)0.0088 (5)0.0016 (5)
C120.0255 (7)0.0323 (8)0.0378 (7)0.0062 (5)0.0074 (5)0.0059 (6)
Geometric parameters (Å, º) top
C1—N11.3471 (16)C4—H40.9500
C1—C81.3858 (18)C5—C61.3842 (17)
C1—H10.9500C5—H50.9500
N1—C21.3874 (16)C6—C71.3936 (18)
N1—H1A0.8800C6—H60.9500
N2—C101.3287 (16)C7—C81.4457 (16)
N2—C121.4591 (16)C8—C91.4380 (17)
N2—C111.4602 (15)C9—C101.5298 (17)
O1—C91.2244 (16)C11—H11A0.9800
O2—C101.2431 (15)C11—H11B0.9800
C2—C31.3906 (17)C11—H11C0.9800
C2—C71.4110 (17)C12—H12A0.9800
C3—C41.380 (2)C12—H12B0.9800
C3—H30.9500C12—H12C0.9800
C4—C51.399 (2)
N1—C1—C8110.00 (11)C6—C7—C2119.39 (11)
N1—C1—H1125.0C6—C7—C8134.46 (12)
C8—C1—H1125.0C2—C7—C8106.09 (11)
C1—N1—C2109.43 (10)C1—C8—C9125.50 (11)
C1—N1—H1A125.3C1—C8—C7106.58 (10)
C2—N1—H1A125.3C9—C8—C7127.92 (12)
C10—N2—C12120.07 (10)O1—C9—C8124.97 (12)
C10—N2—C11123.31 (11)O1—C9—C10118.72 (11)
C12—N2—C11116.46 (10)C8—C9—C10116.23 (11)
N1—C2—C3129.53 (12)O2—C10—N2124.03 (11)
N1—C2—C7107.88 (10)O2—C10—C9118.05 (11)
C3—C2—C7122.53 (12)N2—C10—C9117.91 (10)
C4—C3—C2116.96 (12)N2—C11—H11A109.5
C4—C3—H3121.5N2—C11—H11B109.5
C2—C3—H3121.5H11A—C11—H11B109.5
C3—C4—C5121.36 (12)N2—C11—H11C109.5
C3—C4—H4119.3H11A—C11—H11C109.5
C5—C4—H4119.3H11B—C11—H11C109.5
C6—C5—C4121.63 (13)N2—C12—H12A109.5
C6—C5—H5119.2N2—C12—H12B109.5
C4—C5—H5119.2H12A—C12—H12B109.5
C5—C6—C7118.12 (12)N2—C12—H12C109.5
C5—C6—H6120.9H12A—C12—H12C109.5
C7—C6—H6120.9H12B—C12—H12C109.5
C8—C1—N1—C21.24 (14)C6—C7—C8—C1177.34 (13)
C1—N1—C2—C3175.89 (12)C2—C7—C8—C10.23 (13)
C1—N1—C2—C71.37 (13)C6—C7—C8—C92.1 (2)
N1—C2—C3—C4177.12 (12)C2—C7—C8—C9179.18 (11)
C7—C2—C3—C40.20 (18)C1—C8—C9—O1175.49 (12)
C2—C3—C4—C50.64 (19)C7—C8—C9—O15.2 (2)
C3—C4—C5—C60.6 (2)C1—C8—C9—C101.37 (17)
C4—C5—C6—C70.3 (2)C7—C8—C9—C10177.94 (11)
C5—C6—C7—C21.11 (18)C12—N2—C10—O22.49 (19)
C5—C6—C7—C8175.71 (13)C11—N2—C10—O2177.78 (12)
N1—C2—C7—C6178.59 (11)C12—N2—C10—C9178.11 (11)
C3—C2—C7—C61.10 (18)C11—N2—C10—C92.82 (18)
N1—C2—C7—C80.96 (13)O1—C9—C10—O288.55 (15)
C3—C2—C7—C8176.54 (11)C8—C9—C10—O288.51 (14)
N1—C1—C8—C9179.96 (11)O1—C9—C10—N290.89 (15)
N1—C1—C8—C70.61 (13)C8—C9—C10—N292.05 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.881.922.7885 (14)170
Symmetry code: (i) x+1, y1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H8N2O2C12H12N2O2
Mr188.18216.24
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)9090
a, b, c (Å)5.1253 (4), 19.4363 (14), 8.4953 (6)10.1813 (2), 6.0048 (1), 18.0625 (4)
β (°) 93.251 (3) 97.7222 (8)
V3)844.91 (11)1094.27 (4)
Z44
Radiation typeCu KαMo Kα
µ (mm1)0.880.09
Crystal size (mm)0.30 × 0.08 × 0.060.65 × 0.25 × 0.15
Data collection
DiffractometerBruker X8 Proteum
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
[SADABS (Bruker, 2006) and XABS2 (Parkin et al., 1995)]
Multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.744, 0.9490.943, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
10887, 1518, 1481 4780, 2515, 2031
Rint0.0420.033
(sin θ/λ)max1)0.6050.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.158, 1.24 0.040, 0.112, 1.06
No. of reflections15182515
No. of parameters128147
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.330.23, 0.20

Computer programs: APEX2 (Bruker, 2006), COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Selected geometric parameters (Å, º) for (I) top
N2—C101.323 (4)C8—C91.421 (4)
O2—C101.232 (3)C9—C101.528 (4)
C1—C8—C9126.9 (3)O2—C10—N2124.1 (3)
O1—C9—C8124.1 (3)O2—C10—C9122.3 (2)
O1—C9—C10117.1 (3)N2—C10—C9113.5 (2)
C1—C8—C9—O1178.2 (3)O1—C9—C10—O2149.3 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.922.768 (3)160.2
N2—H2A···O2ii0.882.082.926 (3)160.5
N2—H2B···O2iii0.882.142.898 (3)144.0
Symmetry codes: (i) x1, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z.
Selected geometric parameters (Å, º) for (II) top
N2—C101.3287 (16)C8—C91.4380 (17)
O2—C101.2431 (15)C9—C101.5298 (17)
C1—C8—C9125.50 (11)O2—C10—N2124.03 (11)
O1—C9—C8124.97 (12)O2—C10—C9118.05 (11)
O1—C9—C10118.72 (11)N2—C10—C9117.91 (10)
C1—C8—C9—O1175.49 (12)O1—C9—C10—O288.55 (15)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.881.922.7885 (14)169.6
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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