Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021459/sj2298sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021459/sj2298Isup2.hkl |
CCDC reference: 651567
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (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
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).
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.
All H atoms were located in difference maps and their positions and isotropic displacement parameters were refined freely.
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).
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.
C15H16N2O | F(000) = 1024 |
Mr = 240.30 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/c | Melting point = 391–392 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.5339 (2) Å | Cell parameters from 7775 reflections |
b = 8.7382 (2) Å | θ = 2.0–30.0° |
c = 18.7931 (4) Å | µ = 0.08 mm−1 |
β = 91.3265 (10)° | T = 160 K |
V = 2550.26 (9) Å3 | Prism, colourless |
Z = 8 | 0.33 × 0.25 × 0.25 mm |
Nonius KappaCCD area-detector diffractometer | 5265 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.086 |
Horizontally mounted graphite crystal monochromator | θmax = 30.1°, θmin = 2.2° |
Detector resolution: 9 pixels mm-1 | h = −21→21 |
φ and ω scans with κ offsets | k = −12→12 |
76517 measured reflections | l = −26→26 |
7428 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | All 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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C15H16N2O | V = 2550.26 (9) Å3 |
Mr = 240.30 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.5339 (2) Å | µ = 0.08 mm−1 |
b = 8.7382 (2) Å | T = 160 K |
c = 18.7931 (4) Å | 0.33 × 0.25 × 0.25 mm |
β = 91.3265 (10)° |
Nonius KappaCCD area-detector diffractometer | 5265 reflections with I > 2σ(I) |
76517 measured reflections | Rint = 0.086 |
7428 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.156 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.23 e Å−3 |
7428 reflections | Δρmin = −0.27 e Å−3 |
453 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.01832 (8) | 0.29539 (15) | 0.14883 (7) | 0.0211 (3) | |
C2 | −0.09719 (9) | 0.36679 (17) | 0.13395 (8) | 0.0252 (3) | |
C3 | −0.16398 (9) | 0.28519 (18) | 0.10190 (8) | 0.0302 (3) | |
C4 | −0.15435 (10) | 0.13199 (19) | 0.08551 (8) | 0.0309 (3) | |
C5 | −0.07661 (9) | 0.06029 (17) | 0.10076 (8) | 0.0284 (3) | |
C6 | −0.00904 (9) | 0.14121 (16) | 0.13188 (8) | 0.0250 (3) | |
N7 | 0.05056 (7) | 0.37343 (13) | 0.18421 (6) | 0.0245 (3) | |
C8 | 0.09226 (9) | 0.29551 (17) | 0.24309 (8) | 0.0253 (3) | |
N9 | 0.17586 (7) | 0.22970 (13) | 0.22465 (6) | 0.0218 (2) | |
C10 | 0.23004 (8) | 0.18362 (15) | 0.27643 (7) | 0.0216 (3) | |
O11 | 0.21192 (7) | 0.19959 (13) | 0.33981 (5) | 0.0313 (3) | |
C12 | 0.07677 (8) | 0.52154 (15) | 0.16468 (7) | 0.0220 (3) | |
C13 | 0.05035 (9) | 0.58546 (17) | 0.09968 (8) | 0.0269 (3) | |
C14 | 0.07814 (10) | 0.72975 (18) | 0.07981 (10) | 0.0360 (4) | |
C15 | 0.13260 (11) | 0.81400 (19) | 0.12401 (11) | 0.0417 (5) | |
C16 | 0.15846 (11) | 0.7520 (2) | 0.18810 (11) | 0.0405 (4) | |
C17 | 0.13206 (10) | 0.60693 (19) | 0.20888 (9) | 0.0314 (3) | |
C18 | 0.31169 (10) | 0.10702 (19) | 0.25530 (9) | 0.0316 (3) | |
C1A | 0.41376 (8) | 0.47118 (14) | 0.36084 (7) | 0.0203 (3) | |
C2A | 0.35280 (9) | 0.52647 (16) | 0.31177 (8) | 0.0250 (3) | |
C3A | 0.36483 (10) | 0.50847 (18) | 0.23963 (8) | 0.0316 (3) | |
C4A | 0.43723 (10) | 0.43434 (19) | 0.21546 (8) | 0.0335 (4) | |
C5A | 0.49697 (10) | 0.37669 (19) | 0.26369 (9) | 0.0343 (4) | |
C6A | 0.48578 (9) | 0.39454 (17) | 0.33625 (8) | 0.0285 (3) | |
N7A | 0.40232 (7) | 0.49085 (12) | 0.43557 (6) | 0.0229 (3) | |
C8A | 0.38415 (9) | 0.35492 (15) | 0.47658 (8) | 0.0225 (3) | |
N9A | 0.29531 (7) | 0.30152 (13) | 0.46900 (6) | 0.0211 (2) | |
C10A | 0.24228 (9) | 0.28198 (15) | 0.52379 (7) | 0.0235 (3) | |
O11A | 0.26156 (8) | 0.31970 (13) | 0.58554 (5) | 0.0367 (3) | |
C12A | 0.38663 (8) | 0.63759 (15) | 0.46278 (7) | 0.0200 (3) | |
C13A | 0.41939 (9) | 0.76591 (16) | 0.42782 (8) | 0.0260 (3) | |
C14A | 0.40855 (10) | 0.91092 (17) | 0.45551 (9) | 0.0311 (3) | |
C15A | 0.36551 (10) | 0.93288 (17) | 0.51808 (9) | 0.0308 (3) | |
C16A | 0.33210 (9) | 0.80765 (17) | 0.55239 (8) | 0.0285 (3) | |
C17A | 0.34189 (9) | 0.66043 (16) | 0.52556 (7) | 0.0237 (3) | |
C18A | 0.15771 (11) | 0.2075 (2) | 0.50598 (9) | 0.0335 (4) | |
H2 | −0.1035 (10) | 0.473 (2) | 0.1444 (9) | 0.029 (4)* | |
H3 | −0.2181 (12) | 0.3335 (19) | 0.0918 (9) | 0.034 (4)* | |
H4 | −0.2006 (12) | 0.074 (2) | 0.0649 (10) | 0.041 (5)* | |
H5 | −0.0677 (11) | −0.049 (2) | 0.0879 (10) | 0.040 (5)* | |
H6 | 0.0476 (10) | 0.0891 (18) | 0.1419 (8) | 0.025 (4)* | |
H8A | 0.0546 (11) | 0.2130 (19) | 0.2584 (9) | 0.030 (4)* | |
H8B | 0.1035 (10) | 0.3654 (18) | 0.2828 (9) | 0.026 (4)* | |
H9 | 0.1913 (11) | 0.2184 (19) | 0.1778 (10) | 0.034 (5)* | |
H13 | 0.0134 (11) | 0.528 (2) | 0.0675 (10) | 0.036 (5)* | |
H14 | 0.0616 (14) | 0.772 (2) | 0.0355 (13) | 0.057 (6)* | |
H15 | 0.1532 (13) | 0.913 (3) | 0.1108 (11) | 0.058 (6)* | |
H16 | 0.1992 (14) | 0.811 (2) | 0.2187 (12) | 0.054 (6)* | |
H17 | 0.1503 (12) | 0.568 (2) | 0.2528 (11) | 0.045 (5)* | |
H18A | 0.3210 (14) | 0.105 (2) | 0.2040 (13) | 0.060 (6)* | |
H18B | 0.3085 (15) | −0.006 (3) | 0.2706 (13) | 0.071 (7)* | |
H18C | 0.3611 (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)* | |
H8C | 0.4265 (9) | 0.2723 (17) | 0.4602 (8) | 0.018 (4)* | |
H8D | 0.3939 (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)* | |
H18D | 0.1136 (15) | 0.255 (3) | 0.5299 (13) | 0.068 (7)* | |
H18E | 0.1435 (11) | 0.206 (2) | 0.4542 (11) | 0.040 (5)* | |
H18F | 0.1647 (14) | 0.103 (3) | 0.5248 (13) | 0.071 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0203 (6) | 0.0233 (7) | 0.0198 (6) | −0.0002 (5) | 0.0026 (5) | 0.0043 (5) |
C2 | 0.0233 (7) | 0.0262 (7) | 0.0261 (7) | 0.0041 (5) | 0.0029 (6) | 0.0021 (6) |
C3 | 0.0207 (7) | 0.0413 (9) | 0.0286 (8) | 0.0027 (6) | 0.0000 (6) | 0.0071 (7) |
C4 | 0.0279 (7) | 0.0393 (8) | 0.0255 (8) | −0.0107 (6) | −0.0005 (6) | 0.0021 (6) |
C5 | 0.0339 (8) | 0.0255 (7) | 0.0260 (7) | −0.0052 (6) | 0.0047 (6) | 0.0014 (6) |
C6 | 0.0241 (7) | 0.0238 (7) | 0.0272 (7) | 0.0022 (5) | 0.0040 (6) | 0.0043 (6) |
N7 | 0.0239 (6) | 0.0237 (6) | 0.0258 (6) | −0.0014 (4) | −0.0042 (5) | 0.0056 (5) |
C8 | 0.0246 (7) | 0.0316 (8) | 0.0199 (7) | 0.0026 (6) | 0.0022 (5) | 0.0040 (6) |
N9 | 0.0240 (6) | 0.0267 (6) | 0.0145 (6) | 0.0011 (5) | −0.0010 (4) | 0.0003 (5) |
C10 | 0.0240 (6) | 0.0214 (6) | 0.0192 (6) | −0.0057 (5) | −0.0038 (5) | 0.0015 (5) |
O11 | 0.0319 (5) | 0.0452 (6) | 0.0168 (5) | −0.0048 (5) | −0.0036 (4) | 0.0028 (4) |
C12 | 0.0211 (6) | 0.0213 (6) | 0.0239 (7) | 0.0032 (5) | 0.0064 (5) | −0.0013 (5) |
C13 | 0.0283 (7) | 0.0250 (7) | 0.0276 (8) | 0.0038 (6) | 0.0063 (6) | 0.0020 (6) |
C14 | 0.0334 (8) | 0.0280 (8) | 0.0473 (10) | 0.0088 (6) | 0.0152 (8) | 0.0124 (7) |
C15 | 0.0350 (9) | 0.0220 (8) | 0.0693 (13) | 0.0015 (7) | 0.0237 (9) | 0.0005 (8) |
C16 | 0.0318 (8) | 0.0341 (9) | 0.0563 (12) | −0.0088 (7) | 0.0144 (8) | −0.0161 (8) |
C17 | 0.0273 (7) | 0.0372 (8) | 0.0299 (8) | −0.0038 (6) | 0.0057 (6) | −0.0069 (7) |
C18 | 0.0254 (7) | 0.0361 (9) | 0.0331 (9) | 0.0034 (6) | −0.0051 (6) | 0.0023 (7) |
C1A | 0.0219 (6) | 0.0187 (6) | 0.0204 (6) | −0.0026 (5) | 0.0034 (5) | −0.0004 (5) |
C2A | 0.0246 (7) | 0.0267 (7) | 0.0238 (7) | 0.0054 (6) | 0.0047 (5) | 0.0016 (6) |
C3A | 0.0350 (8) | 0.0367 (8) | 0.0233 (7) | 0.0047 (6) | 0.0022 (6) | 0.0056 (6) |
C4A | 0.0392 (8) | 0.0389 (9) | 0.0230 (7) | 0.0013 (7) | 0.0103 (6) | −0.0019 (7) |
C5A | 0.0274 (7) | 0.0407 (9) | 0.0353 (9) | 0.0040 (7) | 0.0091 (7) | −0.0077 (7) |
C6A | 0.0224 (7) | 0.0319 (8) | 0.0312 (8) | 0.0031 (6) | −0.0013 (6) | −0.0015 (6) |
N7A | 0.0310 (6) | 0.0179 (5) | 0.0199 (6) | −0.0013 (4) | 0.0027 (5) | 0.0012 (4) |
C8A | 0.0266 (7) | 0.0203 (6) | 0.0204 (7) | −0.0006 (5) | −0.0035 (5) | 0.0039 (5) |
N9A | 0.0264 (6) | 0.0221 (6) | 0.0150 (6) | −0.0025 (4) | −0.0006 (5) | 0.0003 (4) |
C10A | 0.0327 (7) | 0.0204 (6) | 0.0174 (7) | −0.0010 (5) | 0.0024 (5) | 0.0026 (5) |
O11A | 0.0500 (7) | 0.0442 (7) | 0.0160 (5) | −0.0127 (5) | 0.0043 (5) | −0.0013 (5) |
C12A | 0.0187 (6) | 0.0212 (6) | 0.0199 (6) | −0.0018 (5) | −0.0028 (5) | −0.0001 (5) |
C13A | 0.0283 (7) | 0.0237 (7) | 0.0263 (7) | −0.0037 (6) | 0.0046 (6) | 0.0005 (6) |
C14A | 0.0357 (8) | 0.0216 (7) | 0.0360 (8) | −0.0048 (6) | 0.0014 (7) | 0.0016 (6) |
C15A | 0.0353 (8) | 0.0232 (7) | 0.0336 (8) | 0.0020 (6) | −0.0037 (6) | −0.0056 (6) |
C16A | 0.0292 (7) | 0.0337 (8) | 0.0227 (7) | −0.0012 (6) | −0.0005 (6) | −0.0072 (6) |
C17A | 0.0250 (7) | 0.0270 (7) | 0.0192 (7) | −0.0050 (6) | −0.0015 (5) | −0.0012 (6) |
C18A | 0.0327 (8) | 0.0416 (9) | 0.0263 (8) | −0.0077 (7) | 0.0060 (7) | 0.0018 (7) |
C1—C6 | 1.3926 (19) | C1A—C6A | 1.3919 (19) |
C1—C2 | 1.3974 (19) | C1A—C2A | 1.393 (2) |
C1—N7 | 1.4208 (18) | C1A—N7A | 1.4301 (17) |
C2—C3 | 1.385 (2) | C2A—C3A | 1.382 (2) |
C2—H2 | 0.956 (17) | C2A—H2' | 0.984 (18) |
C3—C4 | 1.383 (2) | C3A—C4A | 1.384 (2) |
C3—H3 | 0.955 (18) | C3A—H3' | 1.00 (2) |
C4—C5 | 1.385 (2) | C4A—C5A | 1.377 (2) |
C4—H4 | 0.952 (19) | C4A—H4' | 0.97 (2) |
C5—C6 | 1.384 (2) | C5A—C6A | 1.388 (2) |
C5—H5 | 0.996 (18) | C5A—H5' | 1.017 (18) |
C6—H6 | 1.005 (16) | C6A—H6' | 0.969 (18) |
N7—C12 | 1.4080 (17) | N7A—C12A | 1.4039 (17) |
N7—C8 | 1.4403 (18) | N7A—C8A | 1.4473 (17) |
C8—N9 | 1.4690 (18) | C8A—N9A | 1.4606 (18) |
C8—H8A | 0.976 (17) | C8A—H8C | 1.028 (15) |
C8—H8B | 0.977 (17) | C8A—H8D | 0.986 (16) |
N9—C10 | 1.3339 (18) | N9A—C10A | 1.3443 (17) |
N9—H9 | 0.923 (19) | N9A—H9' | 0.85 (2) |
C10—O11 | 1.2381 (16) | C10A—O11A | 1.2365 (17) |
C10—C18 | 1.496 (2) | C10A—C18A | 1.497 (2) |
C12—C13 | 1.396 (2) | C12A—C17A | 1.3974 (19) |
C12—C17 | 1.397 (2) | C12A—C13A | 1.4013 (19) |
C13—C14 | 1.387 (2) | C13A—C14A | 1.382 (2) |
C13—H13 | 0.967 (19) | C13A—H13' | 0.944 (16) |
C14—C15 | 1.384 (3) | C14A—C15A | 1.379 (2) |
C14—H14 | 0.94 (2) | C14A—H14' | 1.04 (2) |
C15—C16 | 1.372 (3) | C15A—C16A | 1.378 (2) |
C15—H15 | 0.96 (2) | C15A—H15' | 0.942 (18) |
C16—C17 | 1.391 (2) | C16A—C17A | 1.391 (2) |
C16—H16 | 0.99 (2) | C16A—H16' | 0.966 (18) |
C17—H17 | 0.93 (2) | C17A—H17' | 1.016 (18) |
C18—H18A | 0.98 (2) | C18A—H18D | 0.93 (2) |
C18—H18B | 1.03 (2) | C18A—H18E | 0.99 (2) |
C18—H18C | 0.97 (2) | C18A—H18F | 0.99 (3) |
C6—C1—C2 | 118.76 (13) | C6A—C1A—C2A | 119.11 (13) |
C6—C1—N7 | 119.38 (12) | C6A—C1A—N7A | 120.19 (13) |
C2—C1—N7 | 121.77 (12) | C2A—C1A—N7A | 120.70 (12) |
C3—C2—C1 | 120.11 (13) | C3A—C2A—C1A | 120.32 (13) |
C3—C2—H2 | 120.7 (10) | C3A—C2A—H2' | 118.6 (10) |
C1—C2—H2 | 119.2 (10) | C1A—C2A—H2' | 121.1 (10) |
C4—C3—C2 | 120.77 (14) | C2A—C3A—C4A | 120.32 (15) |
C4—C3—H3 | 118.8 (10) | C2A—C3A—H3' | 119.9 (11) |
C2—C3—H3 | 120.4 (10) | C4A—C3A—H3' | 119.7 (11) |
C3—C4—C5 | 119.36 (14) | C5A—C4A—C3A | 119.70 (14) |
C3—C4—H4 | 121.2 (11) | C5A—C4A—H4' | 121.2 (11) |
C5—C4—H4 | 119.4 (11) | C3A—C4A—H4' | 119.1 (11) |
C6—C5—C4 | 120.37 (14) | C4A—C5A—C6A | 120.52 (14) |
C6—C5—H5 | 119.0 (10) | C4A—C5A—H5' | 121.6 (10) |
C4—C5—H5 | 120.6 (10) | C6A—C5A—H5' | 117.9 (11) |
C5—C6—C1 | 120.63 (13) | C5A—C6A—C1A | 120.01 (14) |
C5—C6—H6 | 120.0 (9) | C5A—C6A—H6' | 123.6 (10) |
C1—C6—H6 | 119.3 (9) | C1A—C6A—H6' | 116.4 (10) |
C12—N7—C1 | 122.57 (11) | C12A—N7A—C1A | 119.61 (11) |
C12—N7—C8 | 120.47 (12) | C12A—N7A—C8A | 121.19 (11) |
C1—N7—C8 | 116.94 (11) | C1A—N7A—C8A | 117.04 (11) |
N7—C8—N9 | 112.84 (11) | N7A—C8A—N9A | 113.93 (11) |
N7—C8—H8A | 108.2 (10) | N7A—C8A—H8C | 106.4 (8) |
N9—C8—H8A | 108.7 (9) | N9A—C8A—H8C | 110.8 (8) |
N7—C8—H8B | 111.1 (9) | N7A—C8A—H8D | 110.7 (9) |
N9—C8—H8B | 106.3 (9) | N9A—C8A—H8D | 105.8 (9) |
H8A—C8—H8B | 109.6 (13) | H8C—C8A—H8D | 109.1 (12) |
C10—N9—C8 | 119.49 (12) | C10A—N9A—C8A | 124.07 (12) |
C10—N9—H9 | 119.4 (11) | C10A—N9A—H9' | 116.7 (13) |
C8—N9—H9 | 121.1 (11) | C8A—N9A—H9' | 118.9 (13) |
O11—C10—N9 | 120.94 (13) | O11A—C10A—N9A | 123.07 (13) |
O11—C10—C18 | 121.25 (13) | O11A—C10A—C18A | 121.19 (13) |
N9—C10—C18 | 117.76 (13) | N9A—C10A—C18A | 115.73 (13) |
C13—C12—C17 | 118.09 (13) | C17A—C12A—C13A | 118.34 (12) |
C13—C12—N7 | 120.99 (13) | C17A—C12A—N7A | 122.14 (12) |
C17—C12—N7 | 120.90 (13) | C13A—C12A—N7A | 119.47 (12) |
C14—C13—C12 | 120.82 (15) | C14A—C13A—C12A | 120.56 (13) |
C14—C13—H13 | 119.4 (10) | C14A—C13A—H13' | 119.6 (10) |
C12—C13—H13 | 119.8 (10) | C12A—C13A—H13' | 119.8 (10) |
C15—C14—C13 | 120.79 (17) | C15A—C14A—C13A | 120.96 (14) |
C15—C14—H14 | 118.2 (13) | C15A—C14A—H14' | 121.5 (11) |
C13—C14—H14 | 121.0 (13) | C13A—C14A—H14' | 117.5 (11) |
C16—C15—C14 | 118.65 (15) | C16A—C15A—C14A | 118.93 (14) |
C16—C15—H15 | 119.4 (13) | C16A—C15A—H15' | 117.8 (11) |
C14—C15—H15 | 121.9 (13) | C14A—C15A—H15' | 123.3 (11) |
C15—C16—C17 | 121.59 (17) | C15A—C16A—C17A | 121.29 (14) |
C15—C16—H16 | 118.3 (12) | C15A—C16A—H16' | 120.4 (10) |
C17—C16—H16 | 120.1 (12) | C17A—C16A—H16' | 118.3 (10) |
C16—C17—C12 | 120.06 (16) | C16A—C17A—C12A | 119.91 (13) |
C16—C17—H17 | 119.9 (12) | C16A—C17A—H17' | 119.7 (10) |
C12—C17—H17 | 120.0 (12) | C12A—C17A—H17' | 120.3 (10) |
C10—C18—H18A | 114.5 (13) | C10A—C18A—H18D | 110.5 (15) |
C10—C18—H18B | 108.0 (13) | C10A—C18A—H18E | 113.5 (10) |
H18A—C18—H18B | 105.4 (18) | H18D—C18A—H18E | 109.5 (18) |
C10—C18—H18C | 111.0 (12) | C10A—C18A—H18F | 103.6 (13) |
H18A—C18—H18C | 109.1 (17) | H18D—C18A—H18F | 109 (2) |
H18B—C18—H18C | 108.4 (18) | H18E—C18A—H18F | 110.8 (17) |
C6—C1—C2—C3 | −1.0 (2) | C6A—C1A—C2A—C3A | −1.5 (2) |
N7—C1—C2—C3 | −177.43 (13) | N7A—C1A—C2A—C3A | 179.28 (13) |
C1—C2—C3—C4 | 1.3 (2) | C1A—C2A—C3A—C4A | 0.5 (2) |
C2—C3—C4—C5 | −0.7 (2) | C2A—C3A—C4A—C5A | 0.8 (2) |
C3—C4—C5—C6 | −0.2 (2) | C3A—C4A—C5A—C6A | −1.0 (2) |
C4—C5—C6—C1 | 0.5 (2) | C4A—C5A—C6A—C1A | 0.0 (2) |
C2—C1—C6—C5 | 0.1 (2) | C2A—C1A—C6A—C5A | 1.3 (2) |
N7—C1—C6—C5 | 176.64 (12) | N7A—C1A—C6A—C5A | −179.52 (13) |
C6—C1—N7—C12 | 136.58 (13) | C6A—C1A—N7A—C12A | 127.70 (14) |
C2—C1—N7—C12 | −47.00 (18) | C2A—C1A—N7A—C12A | −53.09 (17) |
C6—C1—N7—C8 | −44.83 (17) | C6A—C1A—N7A—C8A | −68.79 (16) |
C2—C1—N7—C8 | 131.58 (13) | C2A—C1A—N7A—C8A | 110.42 (14) |
C12—N7—C8—N9 | −78.30 (16) | C12A—N7A—C8A—N9A | 86.00 (15) |
C1—N7—C8—N9 | 103.09 (14) | C1A—N7A—C8A—N9A | −77.22 (15) |
N7—C8—N9—C10 | 165.61 (12) | N7A—C8A—N9A—C10A | −123.28 (14) |
C8—N9—C10—O11 | −2.1 (2) | C8A—N9A—C10A—O11A | 6.2 (2) |
C8—N9—C10—C18 | 175.69 (13) | C8A—N9A—C10A—C18A | −172.44 (13) |
C1—N7—C12—C13 | −15.10 (19) | C1A—N7A—C12A—C17A | 153.53 (13) |
C8—N7—C12—C13 | 166.36 (12) | C8A—N7A—C12A—C17A | −9.28 (19) |
C1—N7—C12—C17 | 166.83 (12) | C1A—N7A—C12A—C13A | −28.97 (18) |
C8—N7—C12—C17 | −11.70 (19) | C8A—N7A—C12A—C13A | 168.23 (13) |
C17—C12—C13—C14 | −0.2 (2) | C17A—C12A—C13A—C14A | 0.9 (2) |
N7—C12—C13—C14 | −178.29 (12) | N7A—C12A—C13A—C14A | −176.72 (13) |
C12—C13—C14—C15 | −0.1 (2) | C12A—C13A—C14A—C15A | 0.1 (2) |
C13—C14—C15—C16 | −0.2 (2) | C13A—C14A—C15A—C16A | −0.9 (2) |
C14—C15—C16—C17 | 0.8 (2) | C14A—C15A—C16A—C17A | 0.8 (2) |
C15—C16—C17—C12 | −1.1 (2) | C15A—C16A—C17A—C12A | 0.3 (2) |
C13—C12—C17—C16 | 0.7 (2) | C13A—C12A—C17A—C16A | −1.1 (2) |
N7—C12—C17—C16 | 178.87 (13) | N7A—C12A—C17A—C16A | 176.48 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O11Ai | 0.923 (19) | 2.097 (18) | 2.9924 (15) | 163.2 (16) |
C18—H18A···O11Ai | 0.98 (2) | 2.48 (2) | 3.329 (2) | 145.1 (17) |
N9A—H9′···O11 | 0.85 (2) | 2.03 (2) | 2.8671 (16) | 169.7 (18) |
C17A—H17′···O11A | 1.016 (18) | 2.440 (18) | 3.4288 (18) | 164.5 (14) |
C18A—H18E···O11 | 0.99 (2) | 2.42 (2) | 3.254 (2) | 141.2 (14) |
C3—H3···Cg4ii | 0.95 (2) | 2.89 | 3.68 | 141 |
C8—H8A···Cg3ii | 0.98 (2) | 3.14 | 3.92 | 139 |
C8A—H8C···Cg4iii | 1.03 (1) | 3.23 | 3.96 | 129 |
C14—H14···Cg1iv | 0.94 (2) | 2.91 | 3.74 | 148 |
C16A—H16′···Cg3i | 0.97 (2) | 3.19 | 3.97 | 139 |
C17—H17···Cg1v | 0.93 (2) | 2.95 | 3.49 | 118 |
C18—H18C···Cg2 | 0.97 (2) | 2.80 | 3.54 | 134 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −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 formula | C15H16N2O |
Mr | 240.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 160 |
a, b, c (Å) | 15.5339 (2), 8.7382 (2), 18.7931 (4) |
β (°) | 91.3265 (10) |
V (Å3) | 2550.26 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.33 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 76517, 7428, 5265 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.156, 1.06 |
No. of reflections | 7428 |
No. of parameters | 453 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O11Ai | 0.923 (19) | 2.097 (18) | 2.9924 (15) | 163.2 (16) |
C18—H18A···O11Ai | 0.98 (2) | 2.48 (2) | 3.329 (2) | 145.1 (17) |
N9A—H9'···O11 | 0.85 (2) | 2.03 (2) | 2.8671 (16) | 169.7 (18) |
C17A—H17'···O11A | 1.016 (18) | 2.440 (18) | 3.4288 (18) | 164.5 (14) |
C18A—H18E···O11 | 0.99 (2) | 2.42 (2) | 3.254 (2) | 141.2 (14) |
C3—H3···Cg4ii | 0.95 (2) | 2.89 | 3.68 | 141 |
C8—H8A···Cg3ii | 0.98 (2) | 3.14 | 3.92 | 139 |
C8A—H8C···Cg4iii | 1.03 (1) | 3.23 | 3.96 | 129 |
C14—H14···Cg1iv | 0.94 (2) | 2.91 | 3.74 | 148 |
C16A—H16'···Cg3i | 0.97 (2) | 3.19 | 3.97 | 139 |
C17—H17···Cg1v | 0.93 (2) | 2.95 | 3.49 | 118 |
C18—H18C···Cg2 | 0.97 (2) | 2.80 | 3.54 | 134 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −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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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.