5-Chloro-2-methyl-sulfanyl-6-(naphtha-len-1-yl-oxy)-1H-benzimidazole methanol monosolvate.

In the title compound, C18H13ClN2OS·CH3OH, the dihedral angle between the benzimidazole group and the naphth-yloxy moiety [82.89 (5)°] very near to orthogonality. The H atom in the five-membered ring is disordered with equal occupancies at the two N atoms and the H atom of the methano-lic hy-droxy group is disordered with equal occupancies over two sites at the O atom. The methanol mol-ecule acts as a hydrogen-bond acceptor for the amino H atom and donates a hydrogen bond to the nonprotonated ring N atom. As a result, chains are formed running along the a axis.

Related literature

For related literature on compound alpha, see: Rivera et al. (2004 ▶); Vera-Montenegro et al. (2003 ▶); Fairweather (2009 ▶); McConville et al. (2010 ▶). For the synthesis of compound alpha, see: Hernández et al. (2002 ▶).

Experimental

Crystal data

C18H13ClN2OS·CH4O

M = 372.85

Triclinic,

a = 7.4094 (6) Å

b = 9.1941 (8) Å

c = 14.4253 (11) Å

α = 73.978 (7)°

β = 75.315 (7)°

γ = 75.136 (7)°

V = 895.09 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 298 K

0.6 × 0.56 × 0.17 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.785, T max = 0.945

6945 measured reflections

4118 independent reflections

2706 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.112

S = 1.03

4118 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033709/bt6948sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033709/bt6948Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033709/bt6948Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H13ClN2OS·CH4O	Z = 2
Mr = 372.85	F(000) = 388
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4094 (6) Å	Cell parameters from 1801 reflections
b = 9.1941 (8) Å	θ = 3.7–29.3°
c = 14.4253 (11) Å	µ = 0.35 mm−1
α = 73.978 (7)°	T = 298 K
β = 75.315 (7)°	Needle, colourless
γ = 75.136 (7)°	0.6 × 0.56 × 0.17 mm
V = 895.09 (14) Å3

Agilent Xcalibur (Atlas, Gemini) diffractometer	4118 independent reflections
Graphite monochromator	2706 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.021
ω scans	θmax = 29.4°, θmin = 3.7°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012)	h = −9→9
Tmin = 0.785, Tmax = 0.945	k = −11→12
6945 measured reflections	l = −19→16

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.2903P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.22 e Å−3
4118 reflections	Δρmin = −0.27 e Å−3
239 parameters

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. H1N H1O and H2N H2O disordered over two sites with occupancies 0.50:0.50

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.69760 (10)	1.27046 (8)	0.30171 (5)	0.0685 (2)
S1	1.35810 (8)	0.67687 (7)	−0.00019 (5)	0.05141 (19)
O1	1.0904 (3)	1.32293 (17)	0.25994 (12)	0.0550 (4)
N1	1.3436 (3)	0.9102 (2)	0.07959 (14)	0.0411 (5)
N2	1.0553 (2)	0.8595 (2)	0.09667 (14)	0.0369 (4)
C1	1.1882 (3)	1.4079 (2)	0.37612 (16)	0.0384 (5)
C2	1.1589 (3)	1.5608 (3)	0.31968 (17)	0.0461 (6)
H2	1.1211	1.5819	0.2598	0.055*
C3	1.1857 (4)	1.6782 (3)	0.35235 (19)	0.0531 (6)
H3	1.1658	1.7786	0.3145	0.064*
C4	1.2426 (3)	1.6488 (3)	0.4420 (2)	0.0577 (7)
H4	1.2598	1.7295	0.4638	0.069*
C5	1.2729 (3)	1.5026 (3)	0.49713 (19)	0.0535 (6)
H5	1.3111	1.4847	0.5566	0.064*
C6	1.2482 (3)	1.3773 (3)	0.46688 (17)	0.0441 (5)
C7	1.2791 (4)	1.2237 (3)	0.52271 (19)	0.0576 (7)
H7	1.3215	1.2023	0.5814	0.069*
C8	1.2483 (4)	1.1076 (3)	0.4923 (2)	0.0621 (7)
H8	1.2699	1.0073	0.5302	0.075*
C9	1.1837 (4)	1.1363 (3)	0.40414 (18)	0.0551 (6)
H9	1.1605	1.0559	0.3843	0.066*
C10	1.1556 (3)	1.2827 (3)	0.34797 (16)	0.0432 (5)
C11	1.2346 (3)	1.1258 (3)	0.17067 (17)	0.0444 (5)
H11	1.3536	1.1486	0.1626	0.053*
C12	1.0750 (3)	1.2040 (2)	0.22222 (17)	0.0450 (6)
C13	0.8955 (3)	1.1704 (2)	0.23444 (17)	0.0444 (5)
C14	0.8714 (3)	1.0586 (2)	0.19396 (17)	0.0431 (5)
H14	0.7518	1.0373	0.2013	0.052*
C15	1.0327 (3)	0.9795 (2)	0.14192 (15)	0.0358 (5)
C16	1.2126 (3)	1.0114 (2)	0.13086 (16)	0.0374 (5)
C17	1.2424 (3)	0.8228 (2)	0.06164 (15)	0.0371 (5)
C18	1.1676 (3)	0.5843 (3)	0.0082 (2)	0.0549 (6)
H18A	1.2152	0.4998	−0.0242	0.082*
H18B	1.0703	0.6574	−0.023	0.082*
H18C	1.1152	0.5462	0.0761	0.082*
O2	0.7136 (3)	0.7793 (2)	0.10784 (15)	0.0633 (6)
C19	0.6753 (4)	0.6830 (4)	0.2003 (2)	0.0908 (11)
H19A	0.6157	0.7443	0.2481	0.136*
H19B	0.7922	0.6188	0.217	0.136*
H19C	0.5916	0.6191	0.1996	0.136*
H1O	0.837 (16)	0.801 (9)	0.088 (6)	0.136*	0.5
H2O	0.621 (15)	0.832 (10)	0.095 (7)	0.136*	0.5
H1N	1.463 (12)	0.896 (8)	0.068 (5)	0.109*	0.5
H2N	0.969 (12)	0.823 (8)	0.094 (5)	0.109*	0.5

	U11	U22	U33	U12	U13	U23
Cl1	0.0649 (4)	0.0543 (4)	0.0730 (5)	0.0010 (3)	0.0026 (4)	−0.0200 (3)
S1	0.0344 (3)	0.0530 (4)	0.0709 (4)	−0.0078 (3)	−0.0067 (3)	−0.0249 (3)
O1	0.0821 (12)	0.0371 (9)	0.0522 (10)	−0.0096 (8)	−0.0300 (9)	−0.0073 (8)
N1	0.0305 (9)	0.0437 (11)	0.0514 (12)	−0.0136 (9)	−0.0082 (9)	−0.0091 (9)
N2	0.0271 (9)	0.0385 (10)	0.0459 (11)	−0.0081 (8)	−0.0107 (8)	−0.0064 (8)
C1	0.0327 (11)	0.0412 (12)	0.0372 (12)	−0.0052 (9)	−0.0042 (9)	−0.0067 (10)
C2	0.0475 (13)	0.0459 (13)	0.0432 (13)	−0.0124 (11)	−0.0097 (11)	−0.0040 (11)
C3	0.0573 (15)	0.0460 (14)	0.0558 (16)	−0.0179 (12)	−0.0074 (12)	−0.0077 (12)
C4	0.0544 (15)	0.0576 (17)	0.0684 (18)	−0.0211 (13)	−0.0071 (14)	−0.0217 (14)
C5	0.0445 (13)	0.0726 (18)	0.0486 (15)	−0.0121 (13)	−0.0108 (11)	−0.0202 (13)
C6	0.0348 (11)	0.0528 (14)	0.0418 (13)	−0.0048 (10)	−0.0065 (10)	−0.0105 (11)
C7	0.0615 (16)	0.0619 (17)	0.0460 (15)	−0.0019 (13)	−0.0220 (13)	−0.0057 (13)
C8	0.0781 (19)	0.0462 (15)	0.0522 (16)	−0.0023 (13)	−0.0206 (14)	0.0024 (12)
C9	0.0701 (17)	0.0399 (13)	0.0539 (16)	−0.0066 (12)	−0.0181 (13)	−0.0068 (12)
C10	0.0450 (13)	0.0396 (12)	0.0413 (13)	−0.0042 (10)	−0.0110 (10)	−0.0050 (10)
C11	0.0422 (12)	0.0447 (13)	0.0499 (14)	−0.0179 (11)	−0.0130 (11)	−0.0047 (11)
C12	0.0574 (15)	0.0364 (12)	0.0428 (13)	−0.0109 (11)	−0.0159 (11)	−0.0044 (10)
C13	0.0457 (13)	0.0371 (12)	0.0427 (13)	−0.0015 (10)	−0.0075 (10)	−0.0041 (10)
C14	0.0337 (11)	0.0414 (12)	0.0504 (14)	−0.0082 (10)	−0.0100 (10)	−0.0021 (11)
C15	0.0315 (10)	0.0339 (11)	0.0404 (12)	−0.0079 (9)	−0.0121 (9)	−0.0003 (9)
C16	0.0327 (11)	0.0373 (12)	0.0405 (12)	−0.0097 (9)	−0.0078 (9)	−0.0030 (10)
C17	0.0318 (11)	0.0378 (11)	0.0406 (12)	−0.0084 (9)	−0.0095 (9)	−0.0033 (10)
C18	0.0492 (14)	0.0552 (15)	0.0708 (17)	−0.0150 (12)	−0.0165 (13)	−0.0228 (13)
O2	0.0351 (9)	0.0765 (13)	0.0721 (13)	−0.0194 (9)	−0.0170 (9)	0.0068 (10)
C19	0.0643 (19)	0.110 (3)	0.082 (2)	−0.0294 (19)	−0.0245 (17)	0.025 (2)

Cl1—C13	1.737 (2)	C7—C8	1.349 (4)
S1—C17	1.736 (2)	C7—H7	0.93
S1—C18	1.790 (2)	C8—C9	1.405 (3)
O1—C12	1.389 (3)	C8—H8	0.93
O1—C10	1.394 (3)	C9—C10	1.361 (3)
N1—C17	1.341 (3)	C9—H9	0.93
N1—C16	1.381 (3)	C11—C12	1.372 (3)
N1—H1N	0.84 (8)	C11—C16	1.390 (3)
N2—C17	1.338 (3)	C11—H11	0.93
N2—C15	1.386 (3)	C12—C13	1.399 (3)
N2—H2N	0.80 (9)	C13—C14	1.381 (3)
C1—C2	1.410 (3)	C14—C15	1.386 (3)
C1—C10	1.413 (3)	C14—H14	0.93
C1—C6	1.421 (3)	C15—C16	1.398 (3)
C2—C3	1.365 (3)	C18—H18A	0.96
C2—H2	0.93	C18—H18B	0.96
C3—C4	1.396 (3)	C18—H18C	0.96
C3—H3	0.93	O2—C19	1.388 (3)
C4—C5	1.354 (3)	O2—H1O	0.94 (12)
C4—H4	0.93	O2—H2O	0.76 (11)
C5—C6	1.407 (3)	C19—H19A	0.96
C5—H5	0.93	C19—H19B	0.96
C6—C7	1.412 (3)	C19—H19C	0.96
C17—S1—C18	101.75 (11)	O1—C10—C1	114.46 (18)
C12—O1—C10	117.61 (16)	C12—C11—C16	117.8 (2)
C17—N1—C16	105.61 (17)	C12—C11—H11	121.1
C17—N1—H1N	125 (5)	C16—C11—H11	121.1
C16—N1—H1N	129 (5)	C11—C12—O1	119.4 (2)
C17—N2—C15	105.35 (17)	C11—C12—C13	121.4 (2)
C17—N2—H2N	130 (5)	O1—C12—C13	119.2 (2)
C15—N2—H2N	124 (5)	C14—C13—C12	121.3 (2)
C2—C1—C10	123.0 (2)	C14—C13—Cl1	118.85 (18)
C2—C1—C6	119.1 (2)	C12—C13—Cl1	119.81 (18)
C10—C1—C6	117.9 (2)	C13—C14—C15	117.3 (2)
C3—C2—C1	120.5 (2)	C13—C14—H14	121.4
C3—C2—H2	119.8	C15—C14—H14	121.4
C1—C2—H2	119.8	N2—C15—C14	130.70 (19)
C2—C3—C4	120.6 (2)	N2—C15—C16	107.82 (18)
C2—C3—H3	119.7	C14—C15—C16	121.4 (2)
C4—C3—H3	119.7	N1—C16—C11	131.58 (19)
C5—C4—C3	120.0 (2)	N1—C16—C15	107.67 (18)
C5—C4—H4	120	C11—C16—C15	120.7 (2)
C3—C4—H4	120	N2—C17—N1	113.55 (19)
C4—C5—C6	121.8 (2)	N2—C17—S1	126.69 (16)
C4—C5—H5	119.1	N1—C17—S1	119.75 (15)
C6—C5—H5	119.1	S1—C18—H18A	109.5
C5—C6—C7	123.1 (2)	S1—C18—H18B	109.5
C5—C6—C1	118.0 (2)	H18A—C18—H18B	109.5
C7—C6—C1	118.9 (2)	S1—C18—H18C	109.5
C8—C7—C6	121.1 (2)	H18A—C18—H18C	109.5
C8—C7—H7	119.5	H18B—C18—H18C	109.5
C6—C7—H7	119.5	C19—O2—H1O	116 (5)
C7—C8—C9	120.8 (2)	C19—O2—H2O	110 (7)
C7—C8—H8	119.6	O2—C19—H19A	109.5
C9—C8—H8	119.6	O2—C19—H19B	109.5
C10—C9—C8	119.5 (2)	H19A—C19—H19B	109.5
C10—C9—H9	120.3	O2—C19—H19C	109.5
C8—C9—H9	120.3	H19A—C19—H19C	109.5
C9—C10—O1	123.7 (2)	H19B—C19—H19C	109.5
C9—C10—C1	121.8 (2)
C10—C1—C2—C3	177.5 (2)	C10—O1—C12—C13	101.8 (2)
C6—C1—C2—C3	−0.8 (3)	C11—C12—C13—C14	−0.9 (3)
C1—C2—C3—C4	0.1 (4)	O1—C12—C13—C14	176.64 (19)
C2—C3—C4—C5	0.4 (4)	C11—C12—C13—Cl1	179.13 (17)
C3—C4—C5—C6	−0.1 (4)	O1—C12—C13—Cl1	−3.4 (3)
C4—C5—C6—C7	179.9 (2)	C12—C13—C14—C15	0.9 (3)
C4—C5—C6—C1	−0.5 (3)	Cl1—C13—C14—C15	−179.11 (16)
C2—C1—C6—C5	1.0 (3)	C17—N2—C15—C14	−177.1 (2)
C10—C1—C6—C5	−177.3 (2)	C17—N2—C15—C16	0.6 (2)
C2—C1—C6—C7	−179.4 (2)	C13—C14—C15—N2	177.4 (2)
C10—C1—C6—C7	2.3 (3)	C13—C14—C15—C16	0.0 (3)
C5—C6—C7—C8	178.0 (2)	C17—N1—C16—C11	178.3 (2)
C1—C6—C7—C8	−1.6 (4)	C17—N1—C16—C15	0.0 (2)
C6—C7—C8—C9	−0.2 (4)	C12—C11—C16—N1	−177.1 (2)
C7—C8—C9—C10	1.2 (4)	C12—C11—C16—C15	1.0 (3)
C8—C9—C10—O1	−179.4 (2)	N2—C15—C16—N1	−0.4 (2)
C8—C9—C10—C1	−0.5 (4)	C14—C15—C16—N1	177.52 (19)
C12—O1—C10—C9	−7.8 (3)	N2—C15—C16—C11	−178.92 (19)
C12—O1—C10—C1	173.2 (2)	C14—C15—C16—C11	−1.0 (3)
C2—C1—C10—C9	−179.5 (2)	C15—N2—C17—N1	−0.6 (2)
C6—C1—C10—C9	−1.3 (3)	C15—N2—C17—S1	178.42 (16)
C2—C1—C10—O1	−0.5 (3)	C16—N1—C17—N2	0.4 (2)
C6—C1—C10—O1	177.75 (18)	C16—N1—C17—S1	−178.71 (15)
C16—C11—C12—O1	−177.63 (18)	C18—S1—C17—N2	−5.5 (2)
C16—C11—C12—C13	−0.1 (3)	C18—S1—C17—N1	173.50 (18)
C10—O1—C12—C11	−80.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···N2	0.94 (12)	1.87 (11)	2.768 (2)	158 (7)
O2—H2O···N1i	0.76 (11)	2.04 (11)	2.781 (3)	162 (9)
N1—H1N···O2ii	0.84 (8)	2.03 (8)	2.781 (3)	148 (7)
N2—H2N···O2	0.80 (9)	1.99 (9)	2.768 (2)	164 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O⋯N2	0.94 (12)	1.87 (11)	2.768 (2)	158 (7)
O2—H2O⋯N1i	0.76 (11)	2.04 (11)	2.781 (3)	162 (9)
N1—H1N⋯O2ii	0.84 (8)	2.03 (8)	2.781 (3)	148 (7)
N2—H2N⋯O2	0.80 (9)	1.99 (9)	2.768 (2)	164 (7)

Symmetry codes: (i) ; (ii) .