2-(3-Methoxy­salicylideneamino)-1H-benzimidazole monohydrate

The molecule of the title compound, C₁₅H₁₃O₂N₃·H₂O, is nearly planar, with an intramolecular N...O hydrogen bond of 2.616 (2) Å. It exists in the phenol–imine form and the dihedral angle between the two aromatic ring systems is 1.04 (5)°. An unsolvated form, crystallized from the same medium, has also been reported [Odabąsoglu, Albayrak & Büyükgüngör (2005). Acta Cryst. E61, o425–o426].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.062
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.00 Deg.

Author Response: The data were collected on an a STOE IPDS II diffractometer with an image plate detector. Because of the long c parameter (29.091(3)) of the unit cell, the reflection spots were rather close to each other and to prevent the overlopping of these reflections we had to increase the crystal to detector distance to 150 mm resulting decreasing in the theta-full.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5723
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.00 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C3      ..       6.34 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C7      ..       5.20 su
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1     ...       1.01 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   OW     -   H2W    ...       1.04 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-(3-Methoxysalicylideneamino)-1H-benzimidazole monohydrate

Crystal data

C15H13N3O2·H2O	F(000) = 1200
Mr = 285.30	Dx = 1.340 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9918 reflections
a = 11.2152 (14) Å	θ = 1.4–24.0°
b = 8.7122 (10) Å	µ = 0.10 mm^−1
c = 29.091 (3) Å	T = 293 K
β = 95.719 (9)°	Plate, orange
V = 2828.3 (6) Å^3	0.36 × 0.26 × 0.11 mm
Z = 8

Data collection

Stoe IPDS-II diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1167 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm^-1	θmax = 24.0°, θmin = 1.4°
φ or ω scans?	h = −12→12
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.967, Tmax = 0.990	l = −31→33
9918 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0358P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max < 0.001
2193 reflections	Δρmax = 0.13 e Å^−3
207 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.67024 (18)	0.5408 (2)	0.45203 (6)	0.0555 (5)
C2	0.59621 (18)	0.6535 (2)	0.43070 (6)	0.0548 (5)
C3	0.58392 (19)	0.6667 (2)	0.38253 (7)	0.0609 (6)
C4	0.6453 (2)	0.5681 (3)	0.35656 (7)	0.0746 (7)
H4	0.6367	0.5764	0.3245	0.090*
C5	0.7194 (2)	0.4570 (3)	0.37756 (8)	0.0838 (7)
H5	0.7613	0.3916	0.3597	0.101*
C6	0.73165 (19)	0.4427 (2)	0.42455 (7)	0.0739 (7)
H6	0.7813	0.3668	0.4384	0.089*
C7	0.68520 (18)	0.5242 (2)	0.50129 (7)	0.0605 (6)
H7	0.7340	0.4457	0.5141	0.073*
C8	0.65412 (17)	0.5898 (2)	0.57604 (6)	0.0514 (5)
C9	0.63122 (17)	0.6361 (2)	0.64840 (6)	0.0514 (5)
C10	0.60175 (18)	0.6873 (2)	0.69103 (7)	0.0661 (6)
H10	0.5483	0.7678	0.6935	0.079*
C11	0.6552 (2)	0.6135 (3)	0.72952 (7)	0.0720 (6)
H11	0.6375	0.6452	0.7586	0.086*
C12	0.7346 (2)	0.4934 (3)	0.72612 (7)	0.0712 (6)
H12	0.7690	0.4461	0.7529	0.085*
C13	0.76376 (19)	0.4427 (2)	0.68390 (7)	0.0656 (6)
H13	0.8173	0.3621	0.6817	0.079*
C14	0.71067 (17)	0.5158 (2)	0.64447 (6)	0.0527 (5)
C15	0.4943 (2)	0.7995 (3)	0.31578 (6)	0.0953 (8)
H15A	0.4401	0.8828	0.3079	0.143*
H15B	0.4622	0.7067	0.3017	0.143*
H15C	0.5704	0.8213	0.3048	0.143*
N1	0.63388 (14)	0.61348 (17)	0.52855 (5)	0.0542 (4)
N2	0.59603 (15)	0.6815 (2)	0.60393 (5)	0.0542 (4)
N3	0.72446 (14)	0.48799 (18)	0.59829 (5)	0.0570 (4)
O1	0.53381 (12)	0.75330 (15)	0.45497 (5)	0.0662 (4)
O2	0.50960 (13)	0.78099 (17)	0.36510 (4)	0.0783 (5)
OW	0.45013 (17)	0.9129 (2)	0.57019 (6)	0.0903 (6)
H1	0.5583 (19)	0.726 (3)	0.4882 (8)	0.110 (8)*
H2	0.5429 (19)	0.760 (2)	0.5934 (6)	0.087 (8)*
H1W	0.377 (4)	0.917 (4)	0.5824 (11)	0.204 (17)*
H2W	0.483 (4)	1.025 (5)	0.5707 (13)	0.25 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0599 (14)	0.0533 (13)	0.0541 (13)	0.0002 (11)	0.0094 (10)	−0.0059 (10)
C2	0.0604 (14)	0.0538 (12)	0.0513 (12)	−0.0046 (11)	0.0114 (10)	−0.0079 (10)
C3	0.0663 (15)	0.0609 (14)	0.0550 (13)	−0.0082 (12)	0.0041 (11)	−0.0012 (11)
C4	0.0839 (19)	0.0831 (17)	0.0587 (13)	−0.0170 (15)	0.0168 (13)	−0.0157 (13)
C5	0.0900 (19)	0.0859 (19)	0.0798 (18)	0.0015 (15)	0.0296 (14)	−0.0268 (14)
C6	0.0751 (17)	0.0703 (16)	0.0780 (16)	0.0063 (13)	0.0166 (13)	−0.0153 (13)
C7	0.0593 (14)	0.0562 (13)	0.0655 (13)	0.0055 (11)	0.0042 (11)	0.0000 (11)
C8	0.0489 (13)	0.0524 (12)	0.0529 (12)	0.0026 (10)	0.0055 (10)	−0.0005 (10)
C9	0.0499 (13)	0.0525 (12)	0.0518 (12)	−0.0028 (10)	0.0050 (10)	0.0001 (10)
C10	0.0683 (15)	0.0671 (14)	0.0635 (14)	0.0048 (12)	0.0090 (12)	−0.0070 (12)
C11	0.0825 (18)	0.0779 (17)	0.0560 (14)	−0.0116 (14)	0.0089 (12)	−0.0053 (12)
C12	0.0788 (17)	0.0734 (16)	0.0593 (14)	−0.0062 (14)	−0.0037 (12)	0.0067 (12)
C13	0.0667 (15)	0.0645 (14)	0.0648 (14)	0.0030 (11)	0.0031 (11)	0.0064 (11)
C14	0.0509 (13)	0.0537 (12)	0.0533 (12)	−0.0028 (11)	0.0043 (10)	0.0027 (10)
C15	0.100 (2)	0.130 (2)	0.0538 (13)	−0.0247 (17)	−0.0053 (12)	0.0202 (14)
N1	0.0549 (11)	0.0563 (10)	0.0512 (10)	0.0055 (8)	0.0050 (8)	−0.0001 (8)
N2	0.0531 (11)	0.0573 (11)	0.0524 (10)	0.0080 (9)	0.0060 (9)	0.0001 (9)
N3	0.0559 (11)	0.0577 (10)	0.0574 (10)	0.0090 (9)	0.0061 (8)	0.0049 (8)
O1	0.0785 (11)	0.0672 (9)	0.0533 (9)	0.0173 (8)	0.0097 (8)	0.0000 (8)
O2	0.0894 (12)	0.0915 (11)	0.0529 (9)	0.0003 (10)	0.0016 (7)	0.0083 (8)
OW	0.0722 (13)	0.0724 (12)	0.1285 (14)	0.0240 (10)	0.0211 (11)	0.0146 (10)

Geometric parameters (Å, º)

C1—C2	1.391 (2)	C9—C10	1.388 (2)
C1—C6	1.398 (2)	C10—C11	1.376 (2)
C1—C7	1.433 (2)	C10—H10	0.9300
C2—O1	1.357 (2)	C11—C12	1.384 (3)
C2—C3	1.399 (2)	C11—H11	0.9300
C3—O2	1.363 (2)	C12—C13	1.375 (3)
C3—C4	1.373 (3)	C12—H12	0.9300
C4—C5	1.379 (3)	C13—C14	1.393 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.366 (3)	C14—N3	1.389 (2)
C5—H5	0.9300	C15—O2	1.437 (2)
C6—H6	0.9300	C15—H15A	0.9600
C7—N1	1.287 (2)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—N3	1.314 (2)	N2—H2	0.94 (2)
C8—N2	1.351 (2)	O1—H1	1.01 (2)
C8—N1	1.393 (2)	OW—H1W	0.93 (4)
C9—N2	1.373 (2)	OW—H2W	1.04 (4)
C9—C14	1.388 (2)
C2—C1—C6	118.85 (17)	C11—C10—H10	121.5
C2—C1—C7	121.49 (17)	C9—C10—H10	121.5
C6—C1—C7	119.66 (19)	C10—C11—C12	121.76 (19)
O1—C2—C1	122.39 (16)	C10—C11—H11	119.1
O1—C2—C3	117.62 (19)	C12—C11—H11	119.1
C1—C2—C3	119.99 (18)	C13—C12—C11	121.2 (2)
O2—C3—C4	125.00 (19)	C13—C12—H12	119.4
O2—C3—C2	115.35 (18)	C11—C12—H12	119.4
C4—C3—C2	119.6 (2)	C12—C13—C14	117.97 (19)
C3—C4—C5	120.6 (2)	C12—C13—H13	121.0
C3—C4—H4	119.7	C14—C13—H13	121.0
C5—C4—H4	119.7	C9—C14—N3	110.22 (16)
C6—C5—C4	120.2 (2)	C9—C14—C13	120.18 (18)
C6—C5—H5	119.9	N3—C14—C13	129.60 (18)
C4—C5—H5	119.9	O2—C15—H15A	109.5
C5—C6—C1	120.7 (2)	O2—C15—H15B	109.5
C5—C6—H6	119.7	H15A—C15—H15B	109.5
C1—C6—H6	119.7	O2—C15—H15C	109.5
N1—C7—C1	122.69 (18)	H15A—C15—H15C	109.5
N1—C7—H7	118.7	H15B—C15—H15C	109.5
C1—C7—H7	118.7	C7—N1—C8	118.88 (16)
N3—C8—N2	113.90 (16)	C8—N2—C9	106.56 (16)
N3—C8—N1	128.24 (17)	C8—N2—H2	124.3 (12)
N2—C8—N1	117.86 (17)	C9—N2—H2	129.2 (12)
N2—C9—C14	105.46 (16)	C8—N3—C14	103.86 (15)
N2—C9—C10	132.67 (19)	C2—O1—H1	104.2 (12)
C14—C9—C10	121.87 (18)	C3—O2—C15	117.43 (17)
C11—C10—C9	116.98 (19)	H1W—OW—H2W	106 (3)
C6—C1—C2—O1	−179.88 (18)	C11—C12—C13—C14	−0.1 (3)
C7—C1—C2—O1	−0.3 (3)	N2—C9—C14—N3	0.2 (2)
C6—C1—C2—C3	0.2 (3)	C10—C9—C14—N3	−179.92 (17)
C7—C1—C2—C3	179.83 (19)	N2—C9—C14—C13	179.96 (17)
O1—C2—C3—O2	0.3 (3)	C10—C9—C14—C13	−0.2 (3)
C1—C2—C3—O2	−179.84 (17)	C12—C13—C14—C9	0.1 (3)
O1—C2—C3—C4	−179.94 (17)	C12—C13—C14—N3	179.84 (19)
C1—C2—C3—C4	0.0 (3)	C1—C7—N1—C8	−179.51 (17)
O2—C3—C4—C5	179.3 (2)	N3—C8—N1—C7	2.6 (3)
C2—C3—C4—C5	−0.4 (3)	N2—C8—N1—C7	−177.74 (17)
C3—C4—C5—C6	0.7 (3)	N3—C8—N2—C9	0.0 (2)
C4—C5—C6—C1	−0.5 (3)	N1—C8—N2—C9	−179.69 (16)
C2—C1—C6—C5	0.1 (3)	C14—C9—N2—C8	−0.15 (19)
C7—C1—C6—C5	−179.5 (2)	C10—C9—N2—C8	−180.0 (2)
C2—C1—C7—N1	−1.6 (3)	N2—C8—N3—C14	0.1 (2)
C6—C1—C7—N1	178.03 (19)	N1—C8—N3—C14	179.78 (18)
N2—C9—C10—C11	179.99 (19)	C9—C14—N3—C8	−0.2 (2)
C14—C9—C10—C11	0.2 (3)	C13—C14—N3—C8	−179.9 (2)
C9—C10—C11—C12	−0.1 (3)	C4—C3—O2—C15	0.0 (3)
C10—C11—C12—C13	0.1 (3)	C2—C3—O2—C15	179.82 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.01 (2)	1.69 (2)	2.616 (2)	150.6 (19)
N2—H2···OW	0.94 (2)	1.78 (2)	2.717 (2)	175.6 (19)
OW—H1W···N3^i	0.93 (4)	1.91 (4)	2.813 (2)	162 (3)
OW—H2W···O1^ii	1.04 (4)	2.07 (4)	3.009 (2)	148 (3)
OW—H2W···O2^ii	1.04 (4)	2.51 (4)	3.270 (2)	129 (3)
C7—H7···N3	0.93	2.49	2.829 (2)	102

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1, −y+2, −z+1.