2-(4-Methoxy-phen-yl)-6-trifluoro-methyl-1H-pyrrolo[3,2-c]quinoline monohydrate.

In the title compound, C(19)H(13)F(3)N(2)O·H(2)O, the phenyl and pyrroloquinoline ring system are close to coplanar [dihedral angle = 10.94 (4)°]. The meth-oxy group also is almost coplanar with the phenyl ring [5.4 (1)°]. In the crystal structure N-H⋯O(water) and water-quinoline O-H⋯N hydrogen bonds build up a supra-molecular chain-like arrangement along [001]. The remaining H atom of the water mol-ecule does not take part in classical hydrogen bonds. Instead, this O-H bond points toward the center of the phenyl ring of a neighbouring mol-ecule. Weak C-H⋯O and C-H⋯π inter-actions are also present.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For O—H⋯π bonds, see: Atwood et al. (1991 ▶). For the graph-set description of hydrogen-bond systems, see: Bernstein et al. (1995 ▶). For the influence of substituents on the geometry of aromatic rings, see: Domenicano (1988 ▶). For a similar synthesis, see: Dutkiewicz et al. (2010 ▶). For related structures, see: Fan & Chen (1987 ▶); Lynch et al. (2001 ▶); Lynch & McClenaghan (2002 ▶).

Experimental

Crystal data

C19H13F3N2O·H2O

M = 360.33

Monoclinic,

a = 13.838 (1) Å

b = 7.0432 (5) Å

c = 17.758 (2) Å

β = 102.743 (8)°

V = 1688.2 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.99 mm−1

T = 295 K

0.4 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.340, T max = 1.000

5601 measured reflections

3304 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.128

S = 1.07

3304 reflections

296 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013644/im2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013644/im2190Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H13F3N2O·H2O	F(000) = 744
Mr = 360.33	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3587 reflections
a = 13.838 (1) Å	θ = 3.3–75.2°
b = 7.0432 (5) Å	µ = 0.99 mm−1
c = 17.758 (2) Å	T = 295 K
β = 102.743 (8)°	Plate, colourless
V = 1688.2 (2) Å3	0.4 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer	3304 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2767 reflections with I > 2σ(I)
mirror	Rint = 0.013
Detector resolution: 5.2679 pixels mm-1	θmax = 75.3°, θmin = 3.3°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→5
Tmin = 0.340, Tmax = 1.000	l = −22→19
5601 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	All H-atom parameters refined
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0763P)2 + 0.1838P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.009
3304 reflections	Δρmax = 0.19 e Å−3
296 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (10)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.78945 (9)	0.29250 (19)	0.16925 (7)	0.0550 (3)
C2	0.88353 (11)	0.3157 (3)	0.20243 (8)	0.0585 (4)
H2	0.9306 (14)	0.344 (3)	0.1687 (10)	0.071 (5)*
C3	0.92113 (10)	0.3055 (2)	0.28263 (8)	0.0510 (3)
C4	0.85387 (10)	0.26693 (18)	0.32912 (7)	0.0439 (3)
C5	0.75150 (10)	0.24194 (18)	0.29686 (8)	0.0457 (3)
C6	0.67970 (11)	0.2042 (2)	0.34033 (9)	0.0564 (4)
H6	0.6994 (13)	0.196 (3)	0.3971 (11)	0.069 (5)*
C7	0.58263 (12)	0.1830 (3)	0.30423 (10)	0.0684 (5)
H7	0.5303 (15)	0.158 (3)	0.3354 (11)	0.080 (6)*
C8	0.55295 (12)	0.1992 (3)	0.22380 (10)	0.0668 (4)
H8	0.4799 (16)	0.183 (3)	0.1986 (11)	0.080 (6)*
C9	0.62098 (11)	0.2358 (2)	0.18026 (9)	0.0564 (4)
C91	0.58623 (13)	0.2559 (3)	0.09412 (11)	0.0790 (6)
F91A	0.48893 (9)	0.2321 (3)	0.07127 (7)	0.1234 (6)
F91B	0.62834 (10)	0.1319 (2)	0.05506 (7)	0.1118 (5)
F91C	0.60642 (9)	0.4282 (2)	0.06897 (7)	0.1051 (5)
C10	0.72299 (10)	0.25735 (19)	0.21521 (8)	0.0474 (3)
N11	0.90552 (8)	0.26236 (16)	0.40374 (6)	0.0451 (3)
H11	0.8790 (14)	0.233 (2)	0.4455 (11)	0.065 (5)*
C12	1.00454 (10)	0.2982 (2)	0.40618 (8)	0.0472 (3)
C13	1.01616 (10)	0.3251 (2)	0.33251 (8)	0.0560 (4)
H13	1.0773 (14)	0.354 (3)	0.3175 (10)	0.073 (5)*
C14	1.07851 (10)	0.30124 (19)	0.47970 (8)	0.0469 (3)
C15	1.17510 (10)	0.3653 (2)	0.48185 (9)	0.0557 (4)
H15	1.1925 (12)	0.408 (3)	0.4342 (10)	0.067 (5)*
C16	1.24628 (11)	0.3636 (2)	0.54972 (9)	0.0590 (4)
H16	1.3115 (14)	0.409 (3)	0.5519 (10)	0.072 (5)*
C17	1.22347 (10)	0.3006 (2)	0.61766 (8)	0.0528 (3)
C18	1.12861 (11)	0.2388 (2)	0.61730 (9)	0.0547 (4)
H18	1.1117 (13)	0.195 (2)	0.6656 (11)	0.064 (5)*
C19	1.05731 (10)	0.2390 (2)	0.54829 (8)	0.0525 (3)
H19	0.9913 (14)	0.193 (2)	0.5499 (10)	0.064 (5)*
O20	1.29904 (8)	0.30707 (18)	0.68177 (6)	0.0660 (3)
C21	1.27720 (15)	0.2604 (3)	0.75398 (10)	0.0669 (5)
H21A	1.3371 (18)	0.280 (3)	0.7903 (13)	0.090 (7)*
H21B	1.2269 (17)	0.345 (3)	0.7653 (12)	0.089 (6)*
H21C	1.2575 (14)	0.133 (3)	0.7546 (11)	0.078 (6)*
O1W	0.81044 (9)	0.12279 (19)	0.51922 (6)	0.0610 (3)
H1W1	0.7916 (17)	0.165 (3)	0.5623 (13)	0.092 (7)*
H1W2	0.802 (2)	0.008 (4)	0.5170 (15)	0.121 (10)*

	U11	U22	U33	U12	U13	U23
N1	0.0483 (6)	0.0776 (8)	0.0393 (6)	0.0045 (6)	0.0100 (5)	−0.0023 (5)
C2	0.0472 (7)	0.0893 (11)	0.0408 (7)	0.0035 (7)	0.0132 (6)	0.0002 (7)
C3	0.0445 (7)	0.0674 (8)	0.0416 (7)	0.0037 (6)	0.0105 (5)	−0.0016 (6)
C4	0.0430 (7)	0.0504 (7)	0.0378 (6)	0.0029 (5)	0.0077 (5)	−0.0014 (5)
C5	0.0448 (7)	0.0500 (7)	0.0414 (7)	0.0012 (5)	0.0076 (5)	−0.0008 (5)
C6	0.0491 (8)	0.0735 (9)	0.0463 (7)	−0.0054 (7)	0.0100 (6)	0.0035 (7)
C7	0.0489 (8)	0.0975 (12)	0.0597 (9)	−0.0095 (8)	0.0143 (7)	0.0046 (9)
C8	0.0443 (8)	0.0930 (12)	0.0600 (9)	−0.0049 (8)	0.0046 (7)	−0.0004 (8)
C9	0.0463 (8)	0.0711 (9)	0.0487 (8)	0.0016 (6)	0.0043 (6)	−0.0033 (6)
C91	0.0496 (9)	0.1272 (17)	0.0557 (10)	−0.0007 (10)	0.0016 (7)	−0.0078 (10)
F91A	0.0517 (6)	0.2442 (19)	0.0643 (7)	−0.0149 (8)	−0.0089 (5)	0.0008 (8)
F91B	0.0891 (8)	0.1757 (14)	0.0664 (6)	−0.0034 (8)	0.0080 (6)	−0.0496 (8)
F91C	0.0881 (8)	0.1500 (12)	0.0710 (7)	0.0129 (8)	0.0040 (6)	0.0398 (8)
C10	0.0460 (7)	0.0539 (7)	0.0415 (7)	0.0029 (5)	0.0080 (6)	−0.0027 (5)
N11	0.0421 (6)	0.0557 (6)	0.0369 (5)	0.0007 (4)	0.0074 (4)	0.0000 (4)
C12	0.0403 (6)	0.0557 (7)	0.0446 (7)	0.0039 (5)	0.0068 (5)	−0.0019 (5)
C13	0.0410 (7)	0.0829 (10)	0.0446 (7)	0.0022 (7)	0.0108 (6)	0.0002 (7)
C14	0.0412 (7)	0.0537 (7)	0.0444 (7)	0.0042 (5)	0.0061 (5)	−0.0023 (5)
C15	0.0445 (7)	0.0705 (9)	0.0514 (8)	−0.0003 (6)	0.0090 (6)	0.0010 (7)
C16	0.0412 (7)	0.0743 (10)	0.0596 (8)	−0.0019 (7)	0.0069 (6)	−0.0005 (7)
C17	0.0430 (7)	0.0580 (8)	0.0515 (7)	0.0063 (6)	−0.0022 (6)	−0.0032 (6)
C18	0.0495 (8)	0.0667 (9)	0.0457 (8)	0.0007 (6)	0.0054 (6)	0.0027 (6)
C19	0.0415 (7)	0.0682 (9)	0.0459 (7)	−0.0012 (6)	0.0057 (6)	−0.0004 (6)
O20	0.0488 (6)	0.0855 (8)	0.0553 (6)	0.0016 (5)	−0.0065 (5)	−0.0003 (5)
C21	0.0688 (11)	0.0694 (11)	0.0532 (9)	0.0023 (8)	−0.0063 (8)	−0.0012 (8)
O1W	0.0696 (7)	0.0718 (8)	0.0449 (5)	−0.0025 (6)	0.0199 (5)	0.0002 (5)

N1—C2	1.3155 (19)	N11—H11	0.92 (2)
N1—C10	1.3800 (18)	C12—C13	1.3662 (19)
C2—C3	1.4061 (19)	C12—C14	1.4707 (18)
C2—H2	1.00 (2)	C13—H13	0.96 (2)
C3—C4	1.4004 (19)	C14—C19	1.385 (2)
C3—C13	1.4210 (19)	C14—C15	1.403 (2)
C4—N11	1.3601 (17)	C15—C16	1.378 (2)
C4—C5	1.4170 (19)	C15—H15	0.977 (18)
C5—C6	1.411 (2)	C16—C17	1.386 (2)
C5—C10	1.4202 (19)	C16—H16	0.950 (19)
C6—C7	1.363 (2)	C17—O20	1.3663 (16)
C6—H6	0.987 (19)	C17—C18	1.382 (2)
C7—C8	1.401 (2)	C18—C19	1.394 (2)
C7—H7	1.02 (2)	C18—H18	0.988 (19)
C8—C9	1.368 (2)	C19—H19	0.977 (19)
C8—H8	1.02 (2)	O20—C21	1.419 (2)
C9—C10	1.419 (2)	C21—H21A	0.94 (2)
C9—C91	1.506 (2)	C21—H21B	0.97 (2)
C91—F91B	1.327 (2)	C21—H21C	0.94 (2)
C91—F91A	1.328 (2)	O1W—H1W1	0.91 (2)
C91—F91C	1.344 (3)	O1W—H1W2	0.82 (3)
N11—C12	1.3845 (17)
C2—N1—C10	118.69 (12)	C4—N11—H11	124.9 (11)
N1—C2—C3	123.77 (13)	C12—N11—H11	125.7 (11)
N1—C2—H2	117.9 (10)	C13—C12—N11	108.67 (12)
C3—C2—H2	118.3 (10)	C13—C12—C14	129.95 (13)
C4—C3—C2	117.49 (13)	N11—C12—C14	121.38 (12)
C4—C3—C13	107.18 (12)	C12—C13—C3	107.17 (12)
C2—C3—C13	135.34 (14)	C12—C13—H13	126.2 (11)
N11—C4—C3	107.71 (12)	C3—C13—H13	126.6 (11)
N11—C4—C5	130.89 (12)	C19—C14—C15	117.58 (13)
C3—C4—C5	121.39 (12)	C19—C14—C12	122.34 (12)
C6—C5—C4	124.31 (13)	C15—C14—C12	120.07 (13)
C6—C5—C10	120.15 (13)	C16—C15—C14	120.92 (14)
C4—C5—C10	115.54 (12)	C16—C15—H15	119.7 (10)
C7—C6—C5	120.19 (14)	C14—C15—H15	119.4 (10)
C7—C6—H6	119.7 (11)	C15—C16—C17	120.54 (14)
C5—C6—H6	120.1 (11)	C15—C16—H16	121.5 (11)
C6—C7—C8	120.51 (15)	C17—C16—H16	117.9 (11)
C6—C7—H7	120.5 (11)	O20—C17—C18	124.48 (14)
C8—C7—H7	119.0 (11)	O20—C17—C16	115.81 (13)
C9—C8—C7	120.52 (15)	C18—C17—C16	119.70 (13)
C9—C8—H8	120.9 (12)	C17—C18—C19	119.43 (14)
C7—C8—H8	118.6 (12)	C17—C18—H18	120.1 (11)
C8—C9—C10	121.00 (14)	C19—C18—H18	120.5 (11)
C8—C9—C91	119.11 (14)	C14—C19—C18	121.83 (14)
C10—C9—C91	119.88 (14)	C14—C19—H19	120.8 (10)
F91B—C91—F91A	106.84 (17)	C18—C19—H19	117.4 (10)
F91B—C91—F91C	105.85 (17)	C17—O20—C21	117.95 (13)
F91A—C91—F91C	106.47 (18)	O20—C21—H21A	104.7 (14)
F91B—C91—C9	112.99 (17)	O20—C21—H21B	110.5 (13)
F91A—C91—C9	111.93 (16)	H21A—C21—H21B	109.4 (17)
F91C—C91—C9	112.29 (16)	O20—C21—H21C	110.6 (12)
N1—C10—C5	123.12 (13)	H21A—C21—H21C	110.3 (17)
N1—C10—C9	119.26 (13)	H21B—C21—H21C	111.1 (18)
C5—C10—C9	117.63 (13)	H1W1—O1W—H1W2	107 (2)
C4—N11—C12	109.27 (11)
C10—N1—C2—C3	0.5 (3)	C8—C9—C10—N1	179.42 (16)
N1—C2—C3—C4	0.5 (3)	C91—C9—C10—N1	−1.4 (2)
N1—C2—C3—C13	−179.65 (17)	C8—C9—C10—C5	−0.8 (2)
C2—C3—C4—N11	179.62 (13)	C91—C9—C10—C5	178.39 (15)
C13—C3—C4—N11	−0.26 (16)	C3—C4—N11—C12	0.29 (15)
C2—C3—C4—C5	−1.0 (2)	C5—C4—N11—C12	−179.04 (13)
C13—C3—C4—C5	179.15 (13)	C4—N11—C12—C13	−0.21 (16)
N11—C4—C5—C6	−0.2 (2)	C4—N11—C12—C14	−179.70 (12)
C3—C4—C5—C6	−179.49 (14)	N11—C12—C13—C3	0.05 (17)
N11—C4—C5—C10	179.70 (13)	C14—C12—C13—C3	179.47 (14)
C3—C4—C5—C10	0.45 (19)	C4—C3—C13—C12	0.12 (17)
C4—C5—C6—C7	179.73 (15)	C2—C3—C13—C12	−179.72 (18)
C10—C5—C6—C7	−0.2 (2)	C13—C12—C14—C19	−168.59 (16)
C5—C6—C7—C8	−0.3 (3)	N11—C12—C14—C19	10.8 (2)
C6—C7—C8—C9	0.2 (3)	C13—C12—C14—C15	10.1 (2)
C7—C8—C9—C10	0.3 (3)	N11—C12—C14—C15	−170.52 (13)
C7—C8—C9—C91	−178.87 (18)	C19—C14—C15—C16	0.8 (2)
C8—C9—C91—F91B	−121.27 (19)	C12—C14—C15—C16	−177.96 (14)
C10—C9—C91—F91B	59.5 (2)	C14—C15—C16—C17	−0.8 (2)
C8—C9—C91—F91A	−0.6 (3)	C15—C16—C17—O20	−179.21 (14)
C10—C9—C91—F91A	−179.81 (17)	C15—C16—C17—C18	0.0 (2)
C8—C9—C91—F91C	119.09 (18)	O20—C17—C18—C19	179.80 (14)
C10—C9—C91—F91C	−60.1 (2)	C16—C17—C18—C19	0.6 (2)
C2—N1—C10—C5	−1.0 (2)	C15—C14—C19—C18	−0.1 (2)
C2—N1—C10—C9	178.74 (15)	C12—C14—C19—C18	178.60 (13)
C6—C5—C10—N1	−179.48 (14)	C17—C18—C19—C14	−0.6 (2)
C4—C5—C10—N1	0.6 (2)	C18—C17—O20—C21	−4.8 (2)
C6—C5—C10—C9	0.7 (2)	C16—C17—O20—C21	174.42 (15)
C4—C5—C10—C9	−179.21 (12)

CgA, CgB, CgD are the centroids of the C5–C9,C1C, N1,C2–C5,C1C and C14–C19 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1W	0.987 (19)	2.42 (2)	3.340 (2)	155 (2)
N11—H11···O1W	0.92 (2)	1.94 (2)	2.845 (2)	167 (2)
C19—H19···O1W	0.977 (19)	2.49 (2)	3.439 (2)	164 (1)
C8—H8···O20i	1.02 (2)	2.45 (2)	3.427 (2)	160 (2)
O1W—H1W1···N1ii	0.91 (2)	1.93 (2)	2.807 (2)	161 (2)
C21—H21C···CgAiii	0.94 (2)	2.83 (2)	3.550 (2)	135 (2)
C21—H21B···CgBiv	0.97 (2)	2.72 (2)	3.503 (2)	138 (2)
O1W—H1W2···CgDiii	0.82 (3)	2.62 (3)	3.310 (2)	143 (2)

Table 1

Hydrogen-bond geometry (Å, °)

CgA, CgB, CgD are the centroids of the C5–C9,C1C, N1,C2–C5,C1C and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1W	0.987 (19)	2.42 (2)	3.340 (2)	155 (2)
N11—H11⋯O1W	0.92 (2)	1.94 (2)	2.845 (2)	167 (2)
C19—H19⋯O1W	0.977 (19)	2.49 (2)	3.439 (2)	164 (1)
C8—H8⋯O20i	1.02 (2)	2.45 (2)	3.427 (2)	160 (2)
O1W—H1W1⋯N1ii	0.91 (2)	1.93 (2)	2.807 (2)	161 (2)
C21—H21C⋯CgAiii	0.94 (2)	2.83 (2)	3.550 (2)	135 (2)
C21—H21B⋯CgBiv	0.97 (2)	2.72 (2)	3.503 (2)	138 (2)
O1W—H1W2⋯CgDiii	0.82 (3)	2.62 (3)	3.310 (2)	143 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .