Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C14H11N5·0.5H2O, a methyl­ene carbon joins the benzimidazole and benzotriazole units with a C-N bond that is longer than a typical C=N double bond but shorter than a C-N single bond, providing potential as a synthetic auxiliary transformation reagent. A water mol­ecule inter­acts with the organic mol­ecule via inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011853/pk2003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011853/pk2003Isup2.hkl
Contains datablock I

CCDC reference: 643074

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.061
  • wR factor = 0.140
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
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 3 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(Benzimidazol-2-ylmethyl)-1H-benzotriazole hemihydrate top
Crystal data top
C14H11N5·0.5H2OF(000) = 540
Mr = 258.29Dx = 1.257 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 676 reflections
a = 12.973 (3) Åθ = 2.6–23.1°
b = 7.7999 (14) ŵ = 0.08 mm1
c = 13.569 (2) ÅT = 291 K
β = 96.300 (4)°Block, colorless
V = 1364.7 (4) Å30.26 × 0.22 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2688 independent reflections
Radiation source: sealed tube1706 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1416
Tmin = 0.98, Tmax = 0.99k = 69
7118 measured reflectionsl = 1616
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0658P)2]
where P = (Fo2 + 2Fc2)/3
2680 reflections(Δ/σ)max = 0.003
181 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.14 e Å3
Special details top

Experimental. Analyses for C, H and N were made on a Perkin–Elmer 240 C elemental analyser. 1H NMR spectroscopic measurements were carried out on a Bruker AM-500 NMR spectrometer, using TMS (SiMe4) as an internal reference. The solid infared spectra (IR) were obtained from a Bruker IFS66V vacuum-type FT–IR spectrophotometer using KBr pellets.

1-Chloromethylacetic acid benzotriazole (3.66 g, 0.02 mol) and o-phenylenediamine (2.16 g, 0.02 mol) in phosphoric acid was heated and magnetically stirred at 403 K for 2 h. After cooling to room temperature, the resulting green mixture was adjusted to pH 7–8 with 5 M NaOH. The precipitate was filtered and washed with water three times, then the collected solid was recrystallized from ethanol and colorless block-shaped crystals were obtained (yield: 3.83 g, 74.30%). Anal calculated (%) for C28H24N10O: C 65.04, H 4.68, N 27.10; found: C 65.05, H 4.64, N 27.13. IR (KBr pellet, cm-1): 3480, 3033, 2775, 1591, 1536, 1493, 1458, 1440, 1336, 1275, 1224, 1102, 1030. 955, 742. 1H NMR (d6-DMSO): 6.35 (s, 2H), 7.28 (s, 2H), 7.53 (t, 1H), 7.62 (s, 2H), 7.67 (t, 3H), 7.95 (d, 0.5H), 8.19 (d, 0.5H).

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.19173 (16)0.6126 (3)0.17340 (16)0.0278 (5)0.50
H1A0.17360.52080.20430.042*0.50
H1C0.21400.58890.11370.042*0.50
C10.12251 (19)0.6722 (3)0.52813 (17)0.0570 (6)
C20.0871 (3)0.7282 (4)0.6187 (2)0.0809 (8)
H20.12910.71940.67850.097*
C30.0060 (3)0.7922 (4)0.6147 (2)0.0857 (9)
H30.02910.83050.67340.103*
C40.0734 (2)0.8065 (4)0.5268 (2)0.0801 (8)
H40.13970.85100.52840.096*
C50.0414 (2)0.7549 (3)0.43853 (19)0.0601 (6)
H50.08380.76570.37900.072*
C60.05735 (16)0.6858 (3)0.44253 (14)0.0426 (5)
C70.08326 (19)0.6003 (3)0.26753 (16)0.0549 (6)
H7A0.01940.53510.25640.066*
H7B0.13690.53650.23900.066*
C80.06875 (16)0.7687 (3)0.21683 (14)0.0412 (5)
C90.09968 (15)1.0206 (3)0.15950 (14)0.0417 (5)
C100.14196 (19)1.1732 (3)0.13090 (16)0.0553 (6)
H100.21241.19630.14440.066*
C110.0753 (2)1.2890 (3)0.08170 (18)0.0615 (6)
H110.10201.39090.05950.074*
C120.0307 (2)1.2593 (3)0.06384 (18)0.0660 (7)
H120.07371.34230.03200.079*
C130.07297 (19)1.1057 (3)0.09327 (17)0.0582 (6)
H130.14371.08390.08140.070*
C140.00583 (15)0.9874 (3)0.14065 (14)0.0433 (5)
N10.11183 (14)0.6186 (2)0.37273 (12)0.0478 (4)
N20.20516 (16)0.5661 (3)0.41380 (16)0.0636 (6)
N30.21176 (17)0.5978 (3)0.50681 (16)0.0709 (6)
N40.14468 (13)0.8790 (2)0.20897 (13)0.0478 (4)
H4A0.20910.86560.23030.057*0.50
N50.02400 (14)0.8270 (2)0.17675 (12)0.0476 (4)
H5A0.08260.77470.17420.057*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0270 (13)0.0291 (12)0.0276 (11)0.0019 (9)0.0039 (9)0.0014 (9)
C10.0606 (15)0.0553 (14)0.0551 (14)0.0015 (11)0.0067 (11)0.0016 (11)
C20.085 (2)0.077 (2)0.080 (2)0.0024 (16)0.0073 (16)0.0022 (15)
C30.090 (2)0.084 (2)0.084 (2)0.0009 (18)0.0158 (18)0.0027 (17)
C40.080 (2)0.0788 (19)0.0822 (19)0.0005 (16)0.0105 (16)0.0027 (16)
C50.0639 (17)0.0604 (14)0.0568 (14)0.0016 (11)0.0099 (12)0.0007 (12)
C60.0437 (12)0.0434 (11)0.0411 (11)0.0008 (9)0.0060 (9)0.0011 (9)
C70.0559 (14)0.0522 (14)0.0568 (13)0.0000 (10)0.0068 (11)0.0010 (11)
C80.0406 (12)0.0417 (11)0.0412 (11)0.0011 (8)0.0045 (9)0.0005 (9)
C90.0422 (11)0.0426 (11)0.0403 (11)0.0025 (9)0.0044 (8)0.0019 (9)
C100.0556 (14)0.0554 (14)0.0552 (13)0.0017 (11)0.0078 (10)0.0004 (11)
C110.0615 (16)0.0601 (15)0.0630 (14)0.0005 (12)0.0071 (12)0.0012 (12)
C120.0677 (18)0.0656 (16)0.0649 (15)0.0024 (12)0.0088 (13)0.0005 (13)
C130.0554 (14)0.0600 (15)0.0589 (14)0.0012 (11)0.0051 (11)0.0008 (11)
C140.0448 (11)0.0431 (11)0.0421 (11)0.0020 (9)0.0053 (8)0.0003 (9)
N10.0467 (10)0.0488 (10)0.0476 (10)0.0008 (8)0.0044 (8)0.0001 (8)
N20.0623 (13)0.0630 (13)0.0649 (13)0.0003 (10)0.0046 (10)0.0024 (10)
N30.0698 (16)0.0730 (15)0.0691 (14)0.0008 (11)0.0045 (12)0.0011 (11)
N40.0474 (10)0.0464 (10)0.0495 (10)0.0003 (8)0.0054 (8)0.0016 (8)
N50.0468 (10)0.0508 (11)0.0454 (9)0.0014 (8)0.0060 (8)0.0003 (8)
Geometric parameters (Å, º) top
O1—N52.741 (3)C8—N41.321 (3)
O1—H1A0.8500C8—N51.344 (3)
O1—H1C0.8501C9—C101.384 (3)
C1—N31.355 (3)C9—N41.388 (3)
C1—C61.364 (3)C9—C141.389 (3)
C1—C21.426 (4)C10—C111.372 (3)
C2—C31.303 (4)C10—H100.9300
C2—H20.9300C11—C121.389 (4)
C3—C41.404 (4)C11—H110.9300
C3—H30.9300C12—C131.394 (3)
C4—C51.370 (4)C12—H120.9300
C4—H40.9300C13—C141.379 (3)
C5—C61.386 (3)C13—H130.9300
C5—H50.9300C14—N51.373 (3)
C6—N11.349 (3)N1—N21.340 (3)
C7—N11.442 (3)N2—N31.280 (3)
C7—C81.486 (3)N4—H4A0.8600
C7—H7A0.9700N5—H5A0.8600
C7—H7B0.9700
N5—O1—H1A109.3C10—C9—C14121.44 (19)
N5—O1—H1C109.6N4—C9—C14107.12 (17)
H1A—O1—H1C109.5C11—C10—C9117.0 (2)
N3—C1—C6108.4 (2)C11—C10—H10121.5
N3—C1—C2132.8 (2)C9—C10—H10121.5
C6—C1—C2118.8 (2)C10—C11—C12122.3 (2)
C3—C2—C1117.8 (3)C10—C11—H11118.9
C3—C2—H2121.1C12—C11—H11118.9
C1—C2—H2121.1C11—C12—C13120.5 (3)
C2—C3—C4123.6 (3)C11—C12—H12119.8
C2—C3—H3118.2C13—C12—H12119.8
C4—C3—H3118.2C14—C13—C12117.4 (2)
C5—C4—C3119.9 (3)C14—C13—H13121.3
C5—C4—H4120.0C12—C13—H13121.3
C3—C4—H4120.0N5—C14—C13130.7 (2)
C4—C5—C6116.6 (2)N5—C14—C9107.97 (17)
C4—C5—H5121.7C13—C14—C9121.4 (2)
C6—C5—H5121.7N2—N1—C6110.24 (17)
N1—C6—C1104.13 (19)N2—N1—C7120.25 (19)
N1—C6—C5132.6 (2)C6—N1—C7129.50 (19)
C1—C6—C5123.2 (2)N3—N2—N1108.1 (2)
N1—C7—C8112.13 (17)N2—N3—C1109.1 (2)
N1—C7—H7A109.2C8—N4—C9106.23 (17)
C8—C7—H7A109.2C8—N4—H4A126.9
N1—C7—H7B109.2C9—N4—H4A126.9
C8—C7—H7B109.2C8—N5—C14105.75 (18)
H7A—C7—H7B107.9C8—N5—O1118.31 (14)
N4—C8—N5112.93 (18)C14—N5—O1135.80 (14)
N4—C8—C7123.75 (19)C8—N5—H5A127.1
N5—C8—C7123.29 (19)C14—N5—H5A127.1
C10—C9—N4131.44 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N3i0.852.202.958 (3)148
N4—H4A···N4ii0.861.992.835 (3)169
N5—H5A···O10.861.902.741 (3)166
Symmetry codes: (i) x1/2, y+1, z1/2; (ii) x+1/2, y, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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