



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810030072/tk2693sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810030072/tk2693Isup2.hkl |
CCDC reference: 792342
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.134
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 79 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 20 Ang. PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 63
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To pure butane-2,3-dione (1.48 g, 15 mmol), aniline (1.36 g, 15 mmol) and ammonium acetate (1.15 g, 15 mmol) in in ethanol (10 ml) was added benzaldehyde (1.5 g, 15 mmol) over about 1 h with the temperature maintained at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane:ethyl acetate as the eluent. Yield: 1.79 g (48%).
H1W and H2W attached to O1W were located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 – 0.96 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms. The methyl groups were found to be disordered over two positions. They were each refined as an idealized disordered methyl group.
As part of our research (Gayathri et al., 2010a,b), we have synthesized the title compound (I) and report its crystal structure here.
In the title compound (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0037 (7) Å for C5]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7) ° with the phenyl ring (C11—C16) attached to N1 and the phenyl ring (C21—C26) attached to C2, respectively. The dihedral angle between the two phenyl rings is 75.83 (8) °. Intermolecular O1W—H1W···N3 and O1W—H2W···O1W hydrogen bonds are found in the crystal structure (Table 1, Fig. 2).
For related crystal structures and applications of imidazole derivatives, see: Gayathri et al. (2010a,b).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
C17H16N2·H2O | Dx = 1.156 Mg m−3 |
Mr = 266.33 | Melting point: 375 K |
Tetragonal, I41/a | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -I 4ad | Cell parameters from 4027 reflections |
a = 25.5498 (2) Å | θ = 4.9–77.4° |
c = 9.3792 (1) Å | µ = 0.57 mm−1 |
V = 6122.67 (9) Å3 | T = 295 K |
Z = 16 | Irregular plate, colourless |
F(000) = 2272 | 0.53 × 0.42 × 0.18 mm |
Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 3109 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2610 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 77.6°, θmin = 4.9° |
ω scans | h = −29→31 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −31→31 |
Tmin = 0.805, Tmax = 1.000 | l = −6→11 |
8078 measured 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0876P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3 |
3109 reflections | (Δ/σ)max = 0.001 |
189 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C17H16N2·H2O | Z = 16 |
Mr = 266.33 | Cu Kα radiation |
Tetragonal, I41/a | µ = 0.57 mm−1 |
a = 25.5498 (2) Å | T = 295 K |
c = 9.3792 (1) Å | 0.53 × 0.42 × 0.18 mm |
V = 6122.67 (9) Å3 |
Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 3109 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2610 reflections with I > 2σ(I) |
Tmin = 0.805, Tmax = 1.000 | Rint = 0.019 |
8078 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.16 e Å−3 |
3109 reflections | Δρmin = −0.21 e Å−3 |
189 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.00564 (4) | 0.01347 (4) | 0.24242 (9) | 0.0428 (3) | |
N3 | 0.09186 (4) | 0.00845 (4) | 0.23202 (10) | 0.0452 (3) | |
C2 | 0.04817 (4) | −0.01899 (5) | 0.23981 (11) | 0.0412 (3) | |
C4 | 0.07726 (5) | 0.06023 (5) | 0.22951 (13) | 0.0487 (3) | |
C5 | 0.02420 (5) | 0.06453 (5) | 0.23682 (13) | 0.0488 (3) | |
C11 | −0.04871 (4) | −0.00047 (5) | 0.25460 (11) | 0.0421 (3) | |
C12 | −0.07965 (5) | −0.00048 (6) | 0.13375 (13) | 0.0582 (5) | |
C13 | −0.13211 (5) | −0.01271 (7) | 0.14490 (16) | 0.0649 (5) | |
C14 | −0.15362 (5) | −0.02441 (7) | 0.27589 (17) | 0.0618 (4) | |
C15 | −0.12261 (5) | −0.02413 (7) | 0.39614 (15) | 0.0627 (5) | |
C16 | −0.06994 (5) | −0.01241 (6) | 0.38579 (12) | 0.0526 (4) | |
C21 | 0.04616 (5) | −0.07654 (5) | 0.24358 (12) | 0.0473 (3) | |
C22 | 0.01046 (6) | −0.10535 (6) | 0.16451 (16) | 0.0597 (4) | |
C23 | 0.01189 (7) | −0.15977 (6) | 0.1680 (2) | 0.0778 (6) | |
C24 | 0.04837 (8) | −0.18527 (7) | 0.2490 (2) | 0.0856 (7) | |
C25 | 0.08410 (8) | −0.15716 (7) | 0.3262 (2) | 0.0869 (7) | |
C26 | 0.08325 (6) | −0.10288 (6) | 0.32454 (17) | 0.0662 (5) | |
C41 | 0.11729 (7) | 0.10273 (6) | 0.2167 (2) | 0.0696 (5) | |
C51 | −0.01126 (7) | 0.11082 (6) | 0.2437 (2) | 0.0704 (5) | |
O1W | 0.24177 (4) | 0.04630 (4) | 0.44390 (11) | 0.0590 (3) | |
H12 | −0.06522 | 0.00770 | 0.04549 | 0.0699* | |
H13 | −0.15303 | −0.01307 | 0.06375 | 0.0779* | |
H14 | −0.18902 | −0.03247 | 0.28311 | 0.0742* | |
H15 | −0.13718 | −0.03186 | 0.48453 | 0.0753* | |
H16 | −0.04894 | −0.01257 | 0.46680 | 0.0631* | |
H22 | −0.01446 | −0.08828 | 0.10917 | 0.0716* | |
H23 | −0.01212 | −0.17894 | 0.11479 | 0.0933* | |
H24 | 0.04891 | −0.22165 | 0.25155 | 0.1027* | |
H25 | 0.10914 | −0.17460 | 0.38022 | 0.1043* | |
H26 | 0.10756 | −0.08410 | 0.37773 | 0.0794* | |
H41A | 0.15164 | 0.08752 | 0.21390 | 0.1045* | 0.500 |
H41B | 0.11467 | 0.12573 | 0.29733 | 0.1045* | 0.500 |
H41C | 0.11126 | 0.12219 | 0.13073 | 0.1045* | 0.500 |
H41D | 0.10007 | 0.13611 | 0.21408 | 0.1045* | 0.500 |
H41E | 0.13704 | 0.09790 | 0.13064 | 0.1045* | 0.500 |
H41F | 0.14045 | 0.10144 | 0.29724 | 0.1045* | 0.500 |
H51A | −0.04695 | 0.09918 | 0.24795 | 0.1055* | 0.500 |
H51B | −0.00634 | 0.13205 | 0.16032 | 0.1055* | 0.500 |
H51C | −0.00332 | 0.13102 | 0.32724 | 0.1055* | 0.500 |
H51D | 0.00921 | 0.14232 | 0.24239 | 0.1055* | 0.500 |
H51E | −0.03140 | 0.10945 | 0.33002 | 0.1055* | 0.500 |
H51F | −0.03442 | 0.11048 | 0.16310 | 0.1055* | 0.500 |
H1W | 0.2423 (7) | 0.0816 (7) | 0.4596 (18) | 0.064 (4)* | |
H2W | 0.2563 (9) | 0.0340 (9) | 0.520 (2) | 0.095 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0387 (5) | 0.0480 (5) | 0.0416 (5) | −0.0005 (4) | −0.0003 (3) | 0.0024 (4) |
N3 | 0.0396 (5) | 0.0533 (5) | 0.0427 (4) | −0.0041 (4) | 0.0026 (4) | 0.0011 (4) |
C2 | 0.0382 (5) | 0.0498 (6) | 0.0357 (5) | −0.0006 (4) | 0.0019 (4) | 0.0033 (4) |
C4 | 0.0484 (6) | 0.0510 (6) | 0.0468 (6) | −0.0068 (5) | 0.0022 (5) | −0.0010 (5) |
C5 | 0.0512 (6) | 0.0466 (6) | 0.0485 (6) | −0.0023 (5) | −0.0005 (5) | 0.0010 (5) |
C11 | 0.0363 (5) | 0.0498 (6) | 0.0403 (5) | 0.0019 (4) | −0.0005 (4) | 0.0015 (4) |
C12 | 0.0493 (7) | 0.0851 (10) | 0.0402 (6) | −0.0004 (6) | −0.0044 (5) | 0.0102 (6) |
C13 | 0.0463 (7) | 0.0911 (10) | 0.0574 (7) | 0.0015 (6) | −0.0156 (6) | 0.0082 (7) |
C14 | 0.0370 (6) | 0.0771 (9) | 0.0713 (8) | −0.0010 (5) | −0.0022 (6) | 0.0031 (7) |
C15 | 0.0496 (7) | 0.0881 (10) | 0.0505 (7) | −0.0062 (6) | 0.0081 (5) | 0.0060 (7) |
C16 | 0.0457 (6) | 0.0745 (8) | 0.0377 (5) | −0.0039 (5) | −0.0026 (4) | 0.0032 (5) |
C21 | 0.0448 (6) | 0.0486 (6) | 0.0486 (6) | 0.0008 (4) | 0.0111 (5) | 0.0060 (5) |
C22 | 0.0538 (7) | 0.0548 (7) | 0.0705 (8) | −0.0052 (5) | 0.0082 (6) | −0.0030 (6) |
C23 | 0.0768 (10) | 0.0573 (8) | 0.0992 (12) | −0.0150 (7) | 0.0224 (9) | −0.0099 (8) |
C24 | 0.0900 (12) | 0.0491 (8) | 0.1177 (15) | 0.0020 (8) | 0.0344 (11) | 0.0162 (9) |
C25 | 0.0846 (12) | 0.0666 (10) | 0.1096 (14) | 0.0172 (9) | 0.0127 (11) | 0.0349 (10) |
C26 | 0.0621 (8) | 0.0636 (8) | 0.0729 (9) | 0.0066 (6) | 0.0011 (7) | 0.0178 (7) |
C41 | 0.0635 (8) | 0.0572 (8) | 0.0882 (10) | −0.0169 (6) | 0.0119 (8) | −0.0054 (7) |
C51 | 0.0643 (9) | 0.0542 (8) | 0.0926 (11) | 0.0080 (6) | −0.0007 (8) | −0.0011 (7) |
O1W | 0.0640 (5) | 0.0518 (6) | 0.0611 (5) | −0.0050 (4) | −0.0054 (4) | −0.0043 (4) |
O1W—H2W | 0.86 (2) | C12—H12 | 0.9300 |
O1W—H1W | 0.914 (18) | C13—H13 | 0.9300 |
N1—C5 | 1.3891 (16) | C14—H14 | 0.9300 |
N1—C2 | 1.3672 (15) | C15—H15 | 0.9300 |
N1—C11 | 1.4381 (15) | C16—H16 | 0.9300 |
N3—C4 | 1.3748 (16) | C22—H22 | 0.9300 |
N3—C2 | 1.3202 (15) | C23—H23 | 0.9300 |
C2—C21 | 1.4717 (18) | C24—H24 | 0.9300 |
C4—C41 | 1.497 (2) | C25—H25 | 0.9300 |
C4—C5 | 1.3618 (18) | C26—H26 | 0.9300 |
C5—C51 | 1.491 (2) | C41—H41B | 0.9600 |
C11—C12 | 1.3819 (16) | C41—H41A | 0.9600 |
C11—C16 | 1.3789 (16) | C41—H41E | 0.9600 |
C12—C13 | 1.3803 (18) | C41—H41C | 0.9600 |
C13—C14 | 1.379 (2) | C41—H41D | 0.9600 |
C14—C15 | 1.378 (2) | C41—H41F | 0.9600 |
C15—C16 | 1.3820 (18) | C51—H51B | 0.9600 |
C21—C26 | 1.388 (2) | C51—H51C | 0.9600 |
C21—C22 | 1.387 (2) | C51—H51E | 0.9600 |
C22—C23 | 1.391 (2) | C51—H51F | 0.9600 |
C23—C24 | 1.368 (3) | C51—H51D | 0.9600 |
C24—C25 | 1.369 (3) | C51—H51A | 0.9600 |
C25—C26 | 1.387 (2) | ||
O1W···O1Wi | 2.8957 (15) | C41···H51D | 2.9500 |
O1W···O1Wii | 2.8957 (15) | C51···H41D | 2.9300 |
O1W···N3ii | 2.9111 (14) | H1W···N3ii | 2.010 (18) |
O1W···H14iii | 2.8200 | H1W···H41Aii | 2.4700 |
O1W···H2Wi | 2.03 (2) | H1W···C4ii | 2.910 (18) |
O1W···H13iv | 2.7900 | H1W···C2ii | 3.098 (18) |
O1W···H15v | 2.7800 | H2W···O1Wii | 2.03 (2) |
O1W···H41Aii | 2.7900 | H2W···H14v | 2.5200 |
O1W···H14v | 2.9100 | H12···N3vi | 2.7200 |
N3···O1Wi | 2.9111 (14) | H12···C2vi | 2.7300 |
N1···H16v | 2.9400 | H13···O1Wviii | 2.7900 |
N1···H22 | 2.9300 | H14···O1Wvii | 2.8200 |
N3···H26 | 2.7600 | H14···O1Wv | 2.9100 |
N3···H1Wi | 2.010 (18) | H14···H2Wv | 2.5200 |
N3···H12vi | 2.7200 | H15···O1Wv | 2.7800 |
C11···C22 | 3.191 (2) | H16···C2v | 2.8700 |
C12···C22 | 3.544 (2) | H16···N1v | 2.9400 |
C12···C51 | 3.493 (2) | H22···N1 | 2.9300 |
C22···C12 | 3.544 (2) | H22···C11 | 2.7700 |
C22···C11 | 3.191 (2) | H22···C12 | 2.8000 |
C23···C25vii | 3.597 (3) | H24···C24iii | 3.0800 |
C25···C23iii | 3.597 (3) | H24···H51Ci | 2.5600 |
C51···C12 | 3.493 (2) | H25···C23iii | 2.9600 |
C2···H1Wi | 3.098 (18) | H25···C22iii | 3.0600 |
C2···H16v | 2.8700 | H26···N3 | 2.7600 |
C2···H12vi | 2.7300 | H41A···H1Wi | 2.4700 |
C4···H1Wi | 2.910 (18) | H41A···O1Wi | 2.7900 |
C11···H22 | 2.7700 | H41B···C24ii | 2.9900 |
C11···H51A | 2.5500 | H41B···C25ii | 2.8600 |
C11···H51E | 2.9300 | H41B···C26ii | 2.9200 |
C11···H51F | 2.9800 | H41D···C51 | 2.9300 |
C12···H51F | 3.0700 | H41D···H51D | 2.3400 |
C12···H22 | 2.8000 | H41F···C26ii | 3.0900 |
C12···H51A | 2.8900 | H51A···C11 | 2.5500 |
C22···H25vii | 3.0600 | H51A···C12 | 2.8900 |
C23···H25vii | 2.9600 | H51C···C24ii | 2.9800 |
C24···H51Ci | 2.9800 | H51C···H24ii | 2.5600 |
C24···H41Bi | 2.9900 | H51D···C41 | 2.9500 |
C24···H24vii | 3.0800 | H51D···H41D | 2.3400 |
C25···H41Bi | 2.8600 | H51E···C11 | 2.9300 |
C26···H41Fi | 3.0900 | H51F···C11 | 2.9800 |
C26···H41Bi | 2.9200 | H51F···C12 | 3.0700 |
H1W—O1W—H2W | 102.7 (18) | C26—C25—H25 | 120.00 |
C2—N1—C11 | 128.22 (10) | C24—C25—H25 | 120.00 |
C5—N1—C11 | 124.42 (10) | C25—C26—H26 | 120.00 |
C2—N1—C5 | 107.32 (10) | C21—C26—H26 | 120.00 |
C2—N3—C4 | 106.41 (10) | C4—C41—H41A | 109.00 |
N1—C2—N3 | 110.54 (11) | C4—C41—H41C | 109.00 |
N1—C2—C21 | 125.30 (10) | C4—C41—H41D | 109.00 |
N3—C2—C21 | 124.15 (10) | C4—C41—H41B | 109.00 |
N3—C4—C41 | 120.94 (12) | C4—C41—H41F | 109.00 |
C5—C4—C41 | 128.74 (12) | H41A—C41—H41B | 109.00 |
N3—C4—C5 | 110.30 (11) | H41A—C41—H41C | 109.00 |
N1—C5—C51 | 122.40 (12) | H41A—C41—H41D | 141.00 |
C4—C5—C51 | 132.14 (13) | H41A—C41—H41E | 56.00 |
N1—C5—C4 | 105.43 (11) | H41A—C41—H41F | 56.00 |
N1—C11—C16 | 120.37 (10) | C4—C41—H41E | 109.00 |
C12—C11—C16 | 120.46 (11) | H41B—C41—H41D | 56.00 |
N1—C11—C12 | 119.16 (10) | H41B—C41—H41E | 141.00 |
C11—C12—C13 | 119.56 (12) | H41B—C41—H41F | 56.00 |
C12—C13—C14 | 120.25 (13) | H41C—C41—H41D | 56.00 |
C13—C14—C15 | 119.93 (12) | H41C—C41—H41E | 56.00 |
C14—C15—C16 | 120.22 (13) | H41C—C41—H41F | 141.00 |
C11—C16—C15 | 119.58 (11) | H41D—C41—H41E | 109.00 |
C2—C21—C26 | 118.27 (11) | H41D—C41—H41F | 109.00 |
C22—C21—C26 | 118.95 (13) | H41E—C41—H41F | 109.00 |
C2—C21—C22 | 122.71 (11) | H41B—C41—H41C | 109.00 |
C21—C22—C23 | 120.04 (14) | C5—C51—H51B | 109.00 |
C22—C23—C24 | 120.47 (16) | C5—C51—H51C | 109.00 |
C23—C24—C25 | 119.90 (17) | C5—C51—H51A | 109.00 |
C24—C25—C26 | 120.55 (17) | C5—C51—H51E | 109.00 |
C21—C26—C25 | 120.10 (15) | C5—C51—H51F | 109.00 |
C13—C12—H12 | 120.00 | C5—C51—H51D | 109.00 |
C11—C12—H12 | 120.00 | H51A—C51—H51C | 109.00 |
C14—C13—H13 | 120.00 | H51A—C51—H51D | 141.00 |
C12—C13—H13 | 120.00 | H51A—C51—H51E | 56.00 |
C13—C14—H14 | 120.00 | H51A—C51—H51F | 56.00 |
C15—C14—H14 | 120.00 | H51B—C51—H51C | 109.00 |
C16—C15—H15 | 120.00 | H51B—C51—H51D | 56.00 |
C14—C15—H15 | 120.00 | H51B—C51—H51E | 141.00 |
C11—C16—H16 | 120.00 | H51B—C51—H51F | 56.00 |
C15—C16—H16 | 120.00 | H51C—C51—H51D | 56.00 |
C23—C22—H22 | 120.00 | H51C—C51—H51E | 56.00 |
C21—C22—H22 | 120.00 | H51C—C51—H51F | 141.00 |
C22—C23—H23 | 120.00 | H51D—C51—H51E | 109.00 |
C24—C23—H23 | 120.00 | H51D—C51—H51F | 109.00 |
C23—C24—H24 | 120.00 | H51E—C51—H51F | 109.00 |
C25—C24—H24 | 120.00 | H51A—C51—H51B | 109.00 |
C5—N1—C2—N3 | −0.41 (12) | N3—C4—C5—N1 | −0.66 (13) |
C5—N1—C2—C21 | −179.82 (10) | N3—C4—C5—C51 | 177.15 (14) |
C11—N1—C2—N3 | −178.01 (9) | C41—C4—C5—N1 | 177.86 (13) |
C11—N1—C2—C21 | 2.58 (17) | C41—C4—C5—C51 | −4.3 (2) |
C2—N1—C5—C4 | 0.65 (12) | N1—C11—C12—C13 | −178.61 (13) |
C2—N1—C5—C51 | −177.43 (12) | C16—C11—C12—C13 | −0.2 (2) |
C11—N1—C5—C4 | 178.36 (10) | N1—C11—C16—C15 | 177.99 (13) |
C11—N1—C5—C51 | 0.28 (18) | C12—C11—C16—C15 | −0.4 (2) |
C2—N1—C11—C12 | −101.64 (14) | C11—C12—C13—C14 | 0.6 (2) |
C2—N1—C11—C16 | 79.95 (16) | C12—C13—C14—C15 | −0.3 (3) |
C5—N1—C11—C12 | 81.14 (15) | C13—C14—C15—C16 | −0.3 (3) |
C5—N1—C11—C16 | −97.27 (15) | C14—C15—C16—C11 | 0.7 (2) |
C4—N3—C2—N1 | 0.00 (13) | C2—C21—C22—C23 | 177.34 (13) |
C4—N3—C2—C21 | 179.42 (10) | C26—C21—C22—C23 | 0.5 (2) |
C2—N3—C4—C5 | 0.42 (13) | C2—C21—C26—C25 | −177.29 (14) |
C2—N3—C4—C41 | −178.24 (12) | C22—C21—C26—C25 | −0.3 (2) |
N1—C2—C21—C22 | 42.85 (17) | C21—C22—C23—C24 | 0.0 (3) |
N1—C2—C21—C26 | −140.30 (12) | C22—C23—C24—C25 | −0.6 (3) |
N3—C2—C21—C22 | −136.48 (13) | C23—C24—C25—C26 | 0.8 (3) |
N3—C2—C21—C26 | 40.36 (17) | C24—C25—C26—C21 | −0.4 (3) |
Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) y+1/4, −x+1/4, z+1/4; (iii) y+1/4, −x−1/4, −z+3/4; (iv) −y+1/4, x+1/4, −z+1/4; (v) −x, −y, −z+1; (vi) −x, −y, −z; (vii) −y−1/4, x−1/4, −z+3/4; (viii) y−1/4, −x+1/4, −z+1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···N3ii | 0.914 (18) | 2.010 (18) | 2.9111 (14) | 168.6 (16) |
O1W—H2W···O1Wii | 0.86 (2) | 2.03 (2) | 2.8957 (15) | 175 (2) |
Symmetry code: (ii) y+1/4, −x+1/4, z+1/4. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2·H2O |
Mr | 266.33 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 295 |
a, c (Å) | 25.5498 (2), 9.3792 (1) |
V (Å3) | 6122.67 (9) |
Z | 16 |
Radiation type | Cu Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.53 × 0.42 × 0.18 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Ruby Gemini |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.805, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8078, 3109, 2610 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.633 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.134, 1.08 |
No. of reflections | 3109 |
No. of parameters | 189 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.21 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···N3i | 0.914 (18) | 2.010 (18) | 2.9111 (14) | 168.6 (16) |
O1W—H2W···O1Wi | 0.86 (2) | 2.03 (2) | 2.8957 (15) | 175 (2) |
Symmetry code: (i) y+1/4, −x+1/4, z+1/4. |
As part of our research (Gayathri et al., 2010a,b), we have synthesized the title compound (I) and report its crystal structure here.
In the title compound (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0037 (7) Å for C5]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7) ° with the phenyl ring (C11—C16) attached to N1 and the phenyl ring (C21—C26) attached to C2, respectively. The dihedral angle between the two phenyl rings is 75.83 (8) °. Intermolecular O1W—H1W···N3 and O1W—H2W···O1W hydrogen bonds are found in the crystal structure (Table 1, Fig. 2).