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The dihedral angles between the mean planes of the two phenyl rings for the two mol­ecules in the asymmetric unit of the title compound, C15H16N2O, are 55.34 (5) and 71.24 (5)°. In one of the mol­ecules, the entire amino­methylacetamide chain is largely planar, while in the second the chain is twisted significantly at the methyl­ene C atom. In the crystal structure, extended chains form along c through N—H...O hydrogen bonds between the amide groups. Further aggregation is completed by the presence of C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021459/sj2298sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021459/sj2298Isup2.hkl
Contains datablock I

CCDC reference: 651567

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.056
  • wR factor = 0.156
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.94 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Diphenylamine derivatives find applications in DNA detection, plant growth regulation, pesticides (Tomlin, 1997), pharmaceuticals (Bettaieb & Aaron, 2001) and materials science (Shirota, 2005). The present investigation is aimed at the study of the molecular and supramolecular architecture of the title compound, (I). This study may serve as a forerunner to a study of the correlation between the molecular and supramolecular features of this compound and its biological activity.

There are two independent molecules in the asymmetric unit (Fig. 1). The dihedral angles between the mean planes of the two phenyl rings in each independent molecule are 55.34 (5)° and 71.24 (5)°, respectively. The bond lengths are comparable to the values reported for similar compounds (Allen et al., 1987). The plane defined by atoms N7, C8 and N9 is almost coplanar with the mean plane through atoms C8, N9, C10, O11 and C18 (dihedral angle is 16.27 (8)°) in molecule 1, whereas the corresponding planes in molecule 2 intersect at the much larger angle of 61.51 (8)°.

The crystal structure of (I) is stabilized by the interplay of N—H···O, C—H···O and C—H···π interactions (Table 1). The N9—H9···O11Ai (see Table 1 for symmetry codes) and C18—-H18A···O11Ai interactions constitute a pair of bifurcated acceptor bonds generating a motif of graph set (Bernstein et al., 1995; Etter, 1990) R12(6). Similarly, the N9A—H9'···O11 and C18A—H18E···O11 interactions link the two molecules of the asymmetric unit to give a R12(6) motif. The N—H···O interactions generate an infinite chain of alternating symmetry-independent molecules along [001] (Fig. 2), which can be designated with the binary motif of C22(8). An S(8) motif is formed by the C17A—H17'···O11A interaction.

The C18—H18C···Cg2 interaction (Table 1) generates an S(7) motif. This is a special type of motif whose atom count in the pattern is assigned by taking the entire aromatic ring (C12—C17) as a single acceptor atom. The C3—H3···Cg4ii and C8—H8A···Cg3ii interactions together generate an R22(10) motif. Cg1, Cg2, Cg3 & Cg4 (Table 1) refer to the centroids of the C1—C6, C12—C17, C1A—C6A & C12A—C17A rings, respectively.

Related literature top

For applications of diphenylamine derivatives, see Tomlin (1997), Bettaieb & Aaron (2001) and Shirota (2005). A structural isomer [(C6H5)2CHNHCH2CONH2;CSD REFCODE: ACEMAX] of the title compound [(C6H5)2NCH2NHCOCH3] has been reported (Mancilla et al., 2003). For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Etter (1990).

Experimental top

The title compound was synthesized by a Mannich condensation reaction involving acetamide, formaldehyde and diphenylamine in a 1:1:0.5 molar ratio. Acetamide was dissolved in ethanol and, to this solution, formaldehyde was added with stirring. Diphenylamine dissolved in acetone was added in small quantities to the above mixture and stirred. After 10 days, the solid product formed was filtered and washed with distilled water, followed by small quantities of acetone. The compound was dried at 333 K and diffraction quality crystals were obtained by recrystallization from ethanol. Microelemental analysis (Calcd & exptl. values) C 75.0 & 73.01, H 6.6 & 6.19 and N 11.66 & 11.58. Mass spectrum (m/e): 240, 197, 182, 168 Molecular Weight Determination by Rast method: exptl. 246 expected 240.

Refinement top

All H atoms were located in difference maps and their positions and isotropic displacement parameters were refined freely.

Structure description top

Diphenylamine derivatives find applications in DNA detection, plant growth regulation, pesticides (Tomlin, 1997), pharmaceuticals (Bettaieb & Aaron, 2001) and materials science (Shirota, 2005). The present investigation is aimed at the study of the molecular and supramolecular architecture of the title compound, (I). This study may serve as a forerunner to a study of the correlation between the molecular and supramolecular features of this compound and its biological activity.

There are two independent molecules in the asymmetric unit (Fig. 1). The dihedral angles between the mean planes of the two phenyl rings in each independent molecule are 55.34 (5)° and 71.24 (5)°, respectively. The bond lengths are comparable to the values reported for similar compounds (Allen et al., 1987). The plane defined by atoms N7, C8 and N9 is almost coplanar with the mean plane through atoms C8, N9, C10, O11 and C18 (dihedral angle is 16.27 (8)°) in molecule 1, whereas the corresponding planes in molecule 2 intersect at the much larger angle of 61.51 (8)°.

The crystal structure of (I) is stabilized by the interplay of N—H···O, C—H···O and C—H···π interactions (Table 1). The N9—H9···O11Ai (see Table 1 for symmetry codes) and C18—-H18A···O11Ai interactions constitute a pair of bifurcated acceptor bonds generating a motif of graph set (Bernstein et al., 1995; Etter, 1990) R12(6). Similarly, the N9A—H9'···O11 and C18A—H18E···O11 interactions link the two molecules of the asymmetric unit to give a R12(6) motif. The N—H···O interactions generate an infinite chain of alternating symmetry-independent molecules along [001] (Fig. 2), which can be designated with the binary motif of C22(8). An S(8) motif is formed by the C17A—H17'···O11A interaction.

The C18—H18C···Cg2 interaction (Table 1) generates an S(7) motif. This is a special type of motif whose atom count in the pattern is assigned by taking the entire aromatic ring (C12—C17) as a single acceptor atom. The C3—H3···Cg4ii and C8—H8A···Cg3ii interactions together generate an R22(10) motif. Cg1, Cg2, Cg3 & Cg4 (Table 1) refer to the centroids of the C1—C6, C12—C17, C1A—C6A & C12A—C17A rings, respectively.

For applications of diphenylamine derivatives, see Tomlin (1997), Bettaieb & Aaron (2001) and Shirota (2005). A structural isomer [(C6H5)2CHNHCH2CONH2;CSD REFCODE: ACEMAX] of the title compound [(C6H5)2NCH2NHCOCH3] has been reported (Mancilla et al., 2003). For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Etter (1990).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. H-atoms are omitted for clarity.
[Figure 2] Fig. 2. View of the molecule along y-axis showing the one-dimensional chain of N—H···O interactions along [001].
N-[(Diphenylamino)methyl]acetamide top
Crystal data top
C15H16N2OF(000) = 1024
Mr = 240.30Dx = 1.252 Mg m3
Monoclinic, P21/cMelting point = 391–392 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.5339 (2) ÅCell parameters from 7775 reflections
b = 8.7382 (2) Åθ = 2.0–30.0°
c = 18.7931 (4) ŵ = 0.08 mm1
β = 91.3265 (10)°T = 160 K
V = 2550.26 (9) Å3Prism, colourless
Z = 80.33 × 0.25 × 0.25 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
5265 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.086
Horizontally mounted graphite crystal monochromatorθmax = 30.1°, θmin = 2.2°
Detector resolution: 9 pixels mm-1h = 2121
φ and ω scans with κ offsetsk = 1212
76517 measured reflectionsl = 2626
7428 independent 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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0794P)2 + 0.3971P]
where P = (Fo2 + 2Fc2)/3
7428 reflections(Δ/σ)max < 0.001
453 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C15H16N2OV = 2550.26 (9) Å3
Mr = 240.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.5339 (2) ŵ = 0.08 mm1
b = 8.7382 (2) ÅT = 160 K
c = 18.7931 (4) Å0.33 × 0.25 × 0.25 mm
β = 91.3265 (10)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
5265 reflections with I > 2σ(I)
76517 measured reflectionsRint = 0.086
7428 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.156All H-atom parameters refined
S = 1.06Δρmax = 0.23 e Å3
7428 reflectionsΔρmin = 0.27 e Å3
453 parameters
Special details top

Experimental. IR spectrum in KBr: 3257 (NH stretch), 3060 (Ar CH stretch), 2366 (ring C=C), 1637 (CO stretch), 1588 (NH in plane bend), 1493 (CN stretch), 751 & 693 (mono substituted Ar ring) 1H NMR in dmso-d6: 7.3038–6.9624 (Ar), 8.4598 (NH), 1.8418 s (CH3), 5.0 d (CH2) & 3.3552 (water in dmso-d6) p.p.m. 13C NMR in dmso-d6: 169.598 (CO), 146.606, 129.228, 121.715 & 120.912 (Ar), 146.606 (substituted C in ring), 56.116 (CH2 bonded to N) & 22.572 (CH3) p.p.m..

Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.438 (1) Frames collected: 415 Seconds exposure per frame: 36 Degrees rotation per frame: 1.9 Crystal-Detector distance (mm): 30.0

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
C10.01832 (8)0.29539 (15)0.14883 (7)0.0211 (3)
C20.09719 (9)0.36679 (17)0.13395 (8)0.0252 (3)
C30.16398 (9)0.28519 (18)0.10190 (8)0.0302 (3)
C40.15435 (10)0.13199 (19)0.08551 (8)0.0309 (3)
C50.07661 (9)0.06029 (17)0.10076 (8)0.0284 (3)
C60.00904 (9)0.14121 (16)0.13188 (8)0.0250 (3)
N70.05056 (7)0.37343 (13)0.18421 (6)0.0245 (3)
C80.09226 (9)0.29551 (17)0.24309 (8)0.0253 (3)
N90.17586 (7)0.22970 (13)0.22465 (6)0.0218 (2)
C100.23004 (8)0.18362 (15)0.27643 (7)0.0216 (3)
O110.21192 (7)0.19959 (13)0.33981 (5)0.0313 (3)
C120.07677 (8)0.52154 (15)0.16468 (7)0.0220 (3)
C130.05035 (9)0.58546 (17)0.09968 (8)0.0269 (3)
C140.07814 (10)0.72975 (18)0.07981 (10)0.0360 (4)
C150.13260 (11)0.81400 (19)0.12401 (11)0.0417 (5)
C160.15846 (11)0.7520 (2)0.18810 (11)0.0405 (4)
C170.13206 (10)0.60693 (19)0.20888 (9)0.0314 (3)
C180.31169 (10)0.10702 (19)0.25530 (9)0.0316 (3)
C1A0.41376 (8)0.47118 (14)0.36084 (7)0.0203 (3)
C2A0.35280 (9)0.52647 (16)0.31177 (8)0.0250 (3)
C3A0.36483 (10)0.50847 (18)0.23963 (8)0.0316 (3)
C4A0.43723 (10)0.43434 (19)0.21546 (8)0.0335 (4)
C5A0.49697 (10)0.37669 (19)0.26369 (9)0.0343 (4)
C6A0.48578 (9)0.39454 (17)0.33625 (8)0.0285 (3)
N7A0.40232 (7)0.49085 (12)0.43557 (6)0.0229 (3)
C8A0.38415 (9)0.35492 (15)0.47658 (8)0.0225 (3)
N9A0.29531 (7)0.30152 (13)0.46900 (6)0.0211 (2)
C10A0.24228 (9)0.28198 (15)0.52379 (7)0.0235 (3)
O11A0.26156 (8)0.31970 (13)0.58554 (5)0.0367 (3)
C12A0.38663 (8)0.63759 (15)0.46278 (7)0.0200 (3)
C13A0.41939 (9)0.76591 (16)0.42782 (8)0.0260 (3)
C14A0.40855 (10)0.91092 (17)0.45551 (9)0.0311 (3)
C15A0.36551 (10)0.93288 (17)0.51808 (9)0.0308 (3)
C16A0.33210 (9)0.80765 (17)0.55239 (8)0.0285 (3)
C17A0.34189 (9)0.66043 (16)0.52556 (7)0.0237 (3)
C18A0.15771 (11)0.2075 (2)0.50598 (9)0.0335 (4)
H20.1035 (10)0.473 (2)0.1444 (9)0.029 (4)*
H30.2181 (12)0.3335 (19)0.0918 (9)0.034 (4)*
H40.2006 (12)0.074 (2)0.0649 (10)0.041 (5)*
H50.0677 (11)0.049 (2)0.0879 (10)0.040 (5)*
H60.0476 (10)0.0891 (18)0.1419 (8)0.025 (4)*
H8A0.0546 (11)0.2130 (19)0.2584 (9)0.030 (4)*
H8B0.1035 (10)0.3654 (18)0.2828 (9)0.026 (4)*
H90.1913 (11)0.2184 (19)0.1778 (10)0.034 (5)*
H130.0134 (11)0.528 (2)0.0675 (10)0.036 (5)*
H140.0616 (14)0.772 (2)0.0355 (13)0.057 (6)*
H150.1532 (13)0.913 (3)0.1108 (11)0.058 (6)*
H160.1992 (14)0.811 (2)0.2187 (12)0.054 (6)*
H170.1503 (12)0.568 (2)0.2528 (11)0.045 (5)*
H18A0.3210 (14)0.105 (2)0.2040 (13)0.060 (6)*
H18B0.3085 (15)0.006 (3)0.2706 (13)0.071 (7)*
H18C0.3611 (13)0.153 (2)0.2790 (11)0.052 (6)*
H2'0.2999 (11)0.577 (2)0.3275 (9)0.036 (4)*
H3'0.3208 (12)0.548 (2)0.2048 (10)0.045 (5)*
H4'0.4457 (12)0.427 (2)0.1645 (11)0.046 (5)*
H5'0.5507 (12)0.3211 (19)0.2476 (10)0.036 (4)*
H6'0.5273 (11)0.3603 (19)0.3721 (10)0.031 (4)*
H8C0.4265 (9)0.2723 (17)0.4602 (8)0.018 (4)*
H8D0.3939 (9)0.3741 (17)0.5278 (9)0.022 (4)*
H9'0.2768 (12)0.272 (2)0.4283 (11)0.043 (5)*
H13'0.4509 (10)0.7530 (18)0.3859 (9)0.025 (4)*
H14'0.4322 (13)1.002 (2)0.4266 (11)0.054 (6)*
H15'0.3571 (11)1.030 (2)0.5386 (10)0.038 (5)*
H16'0.3000 (11)0.8205 (19)0.5954 (10)0.033 (4)*
H17'0.3179 (10)0.570 (2)0.5525 (9)0.034 (4)*
H18D0.1136 (15)0.255 (3)0.5299 (13)0.068 (7)*
H18E0.1435 (11)0.206 (2)0.4542 (11)0.040 (5)*
H18F0.1647 (14)0.103 (3)0.5248 (13)0.071 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0203 (6)0.0233 (7)0.0198 (6)0.0002 (5)0.0026 (5)0.0043 (5)
C20.0233 (7)0.0262 (7)0.0261 (7)0.0041 (5)0.0029 (6)0.0021 (6)
C30.0207 (7)0.0413 (9)0.0286 (8)0.0027 (6)0.0000 (6)0.0071 (7)
C40.0279 (7)0.0393 (8)0.0255 (8)0.0107 (6)0.0005 (6)0.0021 (6)
C50.0339 (8)0.0255 (7)0.0260 (7)0.0052 (6)0.0047 (6)0.0014 (6)
C60.0241 (7)0.0238 (7)0.0272 (7)0.0022 (5)0.0040 (6)0.0043 (6)
N70.0239 (6)0.0237 (6)0.0258 (6)0.0014 (4)0.0042 (5)0.0056 (5)
C80.0246 (7)0.0316 (8)0.0199 (7)0.0026 (6)0.0022 (5)0.0040 (6)
N90.0240 (6)0.0267 (6)0.0145 (6)0.0011 (5)0.0010 (4)0.0003 (5)
C100.0240 (6)0.0214 (6)0.0192 (6)0.0057 (5)0.0038 (5)0.0015 (5)
O110.0319 (5)0.0452 (6)0.0168 (5)0.0048 (5)0.0036 (4)0.0028 (4)
C120.0211 (6)0.0213 (6)0.0239 (7)0.0032 (5)0.0064 (5)0.0013 (5)
C130.0283 (7)0.0250 (7)0.0276 (8)0.0038 (6)0.0063 (6)0.0020 (6)
C140.0334 (8)0.0280 (8)0.0473 (10)0.0088 (6)0.0152 (8)0.0124 (7)
C150.0350 (9)0.0220 (8)0.0693 (13)0.0015 (7)0.0237 (9)0.0005 (8)
C160.0318 (8)0.0341 (9)0.0563 (12)0.0088 (7)0.0144 (8)0.0161 (8)
C170.0273 (7)0.0372 (8)0.0299 (8)0.0038 (6)0.0057 (6)0.0069 (7)
C180.0254 (7)0.0361 (9)0.0331 (9)0.0034 (6)0.0051 (6)0.0023 (7)
C1A0.0219 (6)0.0187 (6)0.0204 (6)0.0026 (5)0.0034 (5)0.0004 (5)
C2A0.0246 (7)0.0267 (7)0.0238 (7)0.0054 (6)0.0047 (5)0.0016 (6)
C3A0.0350 (8)0.0367 (8)0.0233 (7)0.0047 (6)0.0022 (6)0.0056 (6)
C4A0.0392 (8)0.0389 (9)0.0230 (7)0.0013 (7)0.0103 (6)0.0019 (7)
C5A0.0274 (7)0.0407 (9)0.0353 (9)0.0040 (7)0.0091 (7)0.0077 (7)
C6A0.0224 (7)0.0319 (8)0.0312 (8)0.0031 (6)0.0013 (6)0.0015 (6)
N7A0.0310 (6)0.0179 (5)0.0199 (6)0.0013 (4)0.0027 (5)0.0012 (4)
C8A0.0266 (7)0.0203 (6)0.0204 (7)0.0006 (5)0.0035 (5)0.0039 (5)
N9A0.0264 (6)0.0221 (6)0.0150 (6)0.0025 (4)0.0006 (5)0.0003 (4)
C10A0.0327 (7)0.0204 (6)0.0174 (7)0.0010 (5)0.0024 (5)0.0026 (5)
O11A0.0500 (7)0.0442 (7)0.0160 (5)0.0127 (5)0.0043 (5)0.0013 (5)
C12A0.0187 (6)0.0212 (6)0.0199 (6)0.0018 (5)0.0028 (5)0.0001 (5)
C13A0.0283 (7)0.0237 (7)0.0263 (7)0.0037 (6)0.0046 (6)0.0005 (6)
C14A0.0357 (8)0.0216 (7)0.0360 (8)0.0048 (6)0.0014 (7)0.0016 (6)
C15A0.0353 (8)0.0232 (7)0.0336 (8)0.0020 (6)0.0037 (6)0.0056 (6)
C16A0.0292 (7)0.0337 (8)0.0227 (7)0.0012 (6)0.0005 (6)0.0072 (6)
C17A0.0250 (7)0.0270 (7)0.0192 (7)0.0050 (6)0.0015 (5)0.0012 (6)
C18A0.0327 (8)0.0416 (9)0.0263 (8)0.0077 (7)0.0060 (7)0.0018 (7)
Geometric parameters (Å, º) top
C1—C61.3926 (19)C1A—C6A1.3919 (19)
C1—C21.3974 (19)C1A—C2A1.393 (2)
C1—N71.4208 (18)C1A—N7A1.4301 (17)
C2—C31.385 (2)C2A—C3A1.382 (2)
C2—H20.956 (17)C2A—H2'0.984 (18)
C3—C41.383 (2)C3A—C4A1.384 (2)
C3—H30.955 (18)C3A—H3'1.00 (2)
C4—C51.385 (2)C4A—C5A1.377 (2)
C4—H40.952 (19)C4A—H4'0.97 (2)
C5—C61.384 (2)C5A—C6A1.388 (2)
C5—H50.996 (18)C5A—H5'1.017 (18)
C6—H61.005 (16)C6A—H6'0.969 (18)
N7—C121.4080 (17)N7A—C12A1.4039 (17)
N7—C81.4403 (18)N7A—C8A1.4473 (17)
C8—N91.4690 (18)C8A—N9A1.4606 (18)
C8—H8A0.976 (17)C8A—H8C1.028 (15)
C8—H8B0.977 (17)C8A—H8D0.986 (16)
N9—C101.3339 (18)N9A—C10A1.3443 (17)
N9—H90.923 (19)N9A—H9'0.85 (2)
C10—O111.2381 (16)C10A—O11A1.2365 (17)
C10—C181.496 (2)C10A—C18A1.497 (2)
C12—C131.396 (2)C12A—C17A1.3974 (19)
C12—C171.397 (2)C12A—C13A1.4013 (19)
C13—C141.387 (2)C13A—C14A1.382 (2)
C13—H130.967 (19)C13A—H13'0.944 (16)
C14—C151.384 (3)C14A—C15A1.379 (2)
C14—H140.94 (2)C14A—H14'1.04 (2)
C15—C161.372 (3)C15A—C16A1.378 (2)
C15—H150.96 (2)C15A—H15'0.942 (18)
C16—C171.391 (2)C16A—C17A1.391 (2)
C16—H160.99 (2)C16A—H16'0.966 (18)
C17—H170.93 (2)C17A—H17'1.016 (18)
C18—H18A0.98 (2)C18A—H18D0.93 (2)
C18—H18B1.03 (2)C18A—H18E0.99 (2)
C18—H18C0.97 (2)C18A—H18F0.99 (3)
C6—C1—C2118.76 (13)C6A—C1A—C2A119.11 (13)
C6—C1—N7119.38 (12)C6A—C1A—N7A120.19 (13)
C2—C1—N7121.77 (12)C2A—C1A—N7A120.70 (12)
C3—C2—C1120.11 (13)C3A—C2A—C1A120.32 (13)
C3—C2—H2120.7 (10)C3A—C2A—H2'118.6 (10)
C1—C2—H2119.2 (10)C1A—C2A—H2'121.1 (10)
C4—C3—C2120.77 (14)C2A—C3A—C4A120.32 (15)
C4—C3—H3118.8 (10)C2A—C3A—H3'119.9 (11)
C2—C3—H3120.4 (10)C4A—C3A—H3'119.7 (11)
C3—C4—C5119.36 (14)C5A—C4A—C3A119.70 (14)
C3—C4—H4121.2 (11)C5A—C4A—H4'121.2 (11)
C5—C4—H4119.4 (11)C3A—C4A—H4'119.1 (11)
C6—C5—C4120.37 (14)C4A—C5A—C6A120.52 (14)
C6—C5—H5119.0 (10)C4A—C5A—H5'121.6 (10)
C4—C5—H5120.6 (10)C6A—C5A—H5'117.9 (11)
C5—C6—C1120.63 (13)C5A—C6A—C1A120.01 (14)
C5—C6—H6120.0 (9)C5A—C6A—H6'123.6 (10)
C1—C6—H6119.3 (9)C1A—C6A—H6'116.4 (10)
C12—N7—C1122.57 (11)C12A—N7A—C1A119.61 (11)
C12—N7—C8120.47 (12)C12A—N7A—C8A121.19 (11)
C1—N7—C8116.94 (11)C1A—N7A—C8A117.04 (11)
N7—C8—N9112.84 (11)N7A—C8A—N9A113.93 (11)
N7—C8—H8A108.2 (10)N7A—C8A—H8C106.4 (8)
N9—C8—H8A108.7 (9)N9A—C8A—H8C110.8 (8)
N7—C8—H8B111.1 (9)N7A—C8A—H8D110.7 (9)
N9—C8—H8B106.3 (9)N9A—C8A—H8D105.8 (9)
H8A—C8—H8B109.6 (13)H8C—C8A—H8D109.1 (12)
C10—N9—C8119.49 (12)C10A—N9A—C8A124.07 (12)
C10—N9—H9119.4 (11)C10A—N9A—H9'116.7 (13)
C8—N9—H9121.1 (11)C8A—N9A—H9'118.9 (13)
O11—C10—N9120.94 (13)O11A—C10A—N9A123.07 (13)
O11—C10—C18121.25 (13)O11A—C10A—C18A121.19 (13)
N9—C10—C18117.76 (13)N9A—C10A—C18A115.73 (13)
C13—C12—C17118.09 (13)C17A—C12A—C13A118.34 (12)
C13—C12—N7120.99 (13)C17A—C12A—N7A122.14 (12)
C17—C12—N7120.90 (13)C13A—C12A—N7A119.47 (12)
C14—C13—C12120.82 (15)C14A—C13A—C12A120.56 (13)
C14—C13—H13119.4 (10)C14A—C13A—H13'119.6 (10)
C12—C13—H13119.8 (10)C12A—C13A—H13'119.8 (10)
C15—C14—C13120.79 (17)C15A—C14A—C13A120.96 (14)
C15—C14—H14118.2 (13)C15A—C14A—H14'121.5 (11)
C13—C14—H14121.0 (13)C13A—C14A—H14'117.5 (11)
C16—C15—C14118.65 (15)C16A—C15A—C14A118.93 (14)
C16—C15—H15119.4 (13)C16A—C15A—H15'117.8 (11)
C14—C15—H15121.9 (13)C14A—C15A—H15'123.3 (11)
C15—C16—C17121.59 (17)C15A—C16A—C17A121.29 (14)
C15—C16—H16118.3 (12)C15A—C16A—H16'120.4 (10)
C17—C16—H16120.1 (12)C17A—C16A—H16'118.3 (10)
C16—C17—C12120.06 (16)C16A—C17A—C12A119.91 (13)
C16—C17—H17119.9 (12)C16A—C17A—H17'119.7 (10)
C12—C17—H17120.0 (12)C12A—C17A—H17'120.3 (10)
C10—C18—H18A114.5 (13)C10A—C18A—H18D110.5 (15)
C10—C18—H18B108.0 (13)C10A—C18A—H18E113.5 (10)
H18A—C18—H18B105.4 (18)H18D—C18A—H18E109.5 (18)
C10—C18—H18C111.0 (12)C10A—C18A—H18F103.6 (13)
H18A—C18—H18C109.1 (17)H18D—C18A—H18F109 (2)
H18B—C18—H18C108.4 (18)H18E—C18A—H18F110.8 (17)
C6—C1—C2—C31.0 (2)C6A—C1A—C2A—C3A1.5 (2)
N7—C1—C2—C3177.43 (13)N7A—C1A—C2A—C3A179.28 (13)
C1—C2—C3—C41.3 (2)C1A—C2A—C3A—C4A0.5 (2)
C2—C3—C4—C50.7 (2)C2A—C3A—C4A—C5A0.8 (2)
C3—C4—C5—C60.2 (2)C3A—C4A—C5A—C6A1.0 (2)
C4—C5—C6—C10.5 (2)C4A—C5A—C6A—C1A0.0 (2)
C2—C1—C6—C50.1 (2)C2A—C1A—C6A—C5A1.3 (2)
N7—C1—C6—C5176.64 (12)N7A—C1A—C6A—C5A179.52 (13)
C6—C1—N7—C12136.58 (13)C6A—C1A—N7A—C12A127.70 (14)
C2—C1—N7—C1247.00 (18)C2A—C1A—N7A—C12A53.09 (17)
C6—C1—N7—C844.83 (17)C6A—C1A—N7A—C8A68.79 (16)
C2—C1—N7—C8131.58 (13)C2A—C1A—N7A—C8A110.42 (14)
C12—N7—C8—N978.30 (16)C12A—N7A—C8A—N9A86.00 (15)
C1—N7—C8—N9103.09 (14)C1A—N7A—C8A—N9A77.22 (15)
N7—C8—N9—C10165.61 (12)N7A—C8A—N9A—C10A123.28 (14)
C8—N9—C10—O112.1 (2)C8A—N9A—C10A—O11A6.2 (2)
C8—N9—C10—C18175.69 (13)C8A—N9A—C10A—C18A172.44 (13)
C1—N7—C12—C1315.10 (19)C1A—N7A—C12A—C17A153.53 (13)
C8—N7—C12—C13166.36 (12)C8A—N7A—C12A—C17A9.28 (19)
C1—N7—C12—C17166.83 (12)C1A—N7A—C12A—C13A28.97 (18)
C8—N7—C12—C1711.70 (19)C8A—N7A—C12A—C13A168.23 (13)
C17—C12—C13—C140.2 (2)C17A—C12A—C13A—C14A0.9 (2)
N7—C12—C13—C14178.29 (12)N7A—C12A—C13A—C14A176.72 (13)
C12—C13—C14—C150.1 (2)C12A—C13A—C14A—C15A0.1 (2)
C13—C14—C15—C160.2 (2)C13A—C14A—C15A—C16A0.9 (2)
C14—C15—C16—C170.8 (2)C14A—C15A—C16A—C17A0.8 (2)
C15—C16—C17—C121.1 (2)C15A—C16A—C17A—C12A0.3 (2)
C13—C12—C17—C160.7 (2)C13A—C12A—C17A—C16A1.1 (2)
N7—C12—C17—C16178.87 (13)N7A—C12A—C17A—C16A176.48 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9···O11Ai0.923 (19)2.097 (18)2.9924 (15)163.2 (16)
C18—H18A···O11Ai0.98 (2)2.48 (2)3.329 (2)145.1 (17)
N9A—H9···O110.85 (2)2.03 (2)2.8671 (16)169.7 (18)
C17A—H17···O11A1.016 (18)2.440 (18)3.4288 (18)164.5 (14)
C18A—H18E···O110.99 (2)2.42 (2)3.254 (2)141.2 (14)
C3—H3···Cg4ii0.95 (2)2.893.68141
C8—H8A···Cg3ii0.98 (2)3.143.92139
C8A—H8C···Cg4iii1.03 (1)3.233.96129
C14—H14···Cg1iv0.94 (2)2.913.74148
C16A—H16···Cg3i0.97 (2)3.193.97139
C17—H17···Cg1v0.93 (2)2.953.49118
C18—H18C···Cg20.97 (2)2.803.54134
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x, y+1, z; (v) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H16N2O
Mr240.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)160
a, b, c (Å)15.5339 (2), 8.7382 (2), 18.7931 (4)
β (°) 91.3265 (10)
V3)2550.26 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.33 × 0.25 × 0.25
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
76517, 7428, 5265
Rint0.086
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.156, 1.06
No. of reflections7428
No. of parameters453
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.23, 0.27

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9···O11Ai0.923 (19)2.097 (18)2.9924 (15)163.2 (16)
C18—H18A···O11Ai0.98 (2)2.48 (2)3.329 (2)145.1 (17)
N9A—H9'···O110.85 (2)2.03 (2)2.8671 (16)169.7 (18)
C17A—H17'···O11A1.016 (18)2.440 (18)3.4288 (18)164.5 (14)
C18A—H18E···O110.99 (2)2.42 (2)3.254 (2)141.2 (14)
C3—H3···Cg4ii0.95 (2)2.893.68141
C8—H8A···Cg3ii0.98 (2)3.143.92139
C8A—H8C···Cg4iii1.03 (1)3.233.96129
C14—H14···Cg1iv0.94 (2)2.913.74148
C16A—H16'···Cg3i0.97 (2)3.193.97139
C17—H17···Cg1v0.93 (2)2.953.49118
C18—H18C···Cg20.97 (2)2.803.54134
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x, y+1, z; (v) x, y+1/2, z+1/2.
 

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