2-Phenyl­pyrrolo­[2,3-h]­quinoline dihydrate

The crystal structure of the title compound, C₁₇H₁₂N₂·2H₂O, comprises an essentially flat mol­ecule, with the phenyl ring being inclined at 18.7 (1)° to the plane of the pyrrolo­[2,3-h]­quinoline moiety, packed with two water mol­ecules per asymmetric unit, all in a tetragonal lattice. One water mol­ecule is involved in hydrogen-bonding associations with both pyrrolo-NH and quinoline-N sites while, as part of the overall hydrogen-bonding network, both water mol­ecules and their symmetry equivalents construct a `Chinese lantern' arrangement.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.093
• Data-to-parameter ratio = 8.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               1838
         Count of symmetry unique reflns         1849
         Completeness (_total/calc)             99.41%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

The title compound, (I), was prepared from a two-stage procedure starting with the reaction of 8-hydrazinoquinoline dihydrochloride hydrate and acetophenone, followed by the cyclization of the intermediate product (E)-2-acetylbenzene-8-quinonylhydrozone. A structural example of this intermediate, as the thiophene derivative, has been previously published (Lynch & McClenaghan, 2001a). Furthermore, the structure of 2-(4-pyridyl)pyrrolo[3,2-h]quinoline, a product analogous to the title compound, has also been reported (Lynch & McClenaghan, 2001b). We are currently studying the structural aspects of derivatives of both 8-quinonylhydrozone and pyrrolo[3,2-h]quinoline before studying their potential as metal-chelating agents.

The molecule of (I) (Fig. 1) is essentially flat, with the phenyl ring being inclined at 18.7 (1)° to the plane of the pyrrolo[2,3-h]quinoline moiety. It crystallizes with two water molecules per asymmetric unit. One O—H site from one water molecule resides in an hydrogen-bonded triangular arrangement with both pyrrolo-NH and quinoline-N sites. The other O—H site, in conjunction with the second water molecule and their symmetry-related analogues, then forms an hydrogen-bonded "Chinese lantern" arrangement (Fig. 2).

S2. Experimental

The title compound was obtained from Key Organics Ltd and crystals were grown from an ethanol solution.

S3. Refinement

All aromatic H atoms were included in the refinement, at calculated positions, as riding models, with C—H set to 0.95 Å. All water H atoms were initially located in a difference synthesis, but were then restrained to a distance of 0.83 Å, with riding displacement parameters. The remaining N-attached H atom was located in a difference synthesis; its positional and displacement parameters were refined. In the absence of significant anomalous scattering effects, the absolute structure can not be determined; Friedel pairs were merged.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability ellipsoids.
	Fig. 2. Partial packing diagram, showing the hydrogen-bonded "Chinese lantern" arrangement of the water molecules. Hydrogen-bonding associations are shown as dotted lines.

2-phenylpyrrolo[2,3-h]quinoline dihydrate

Crystal data

C17H12N2·2H2O	Dx = 1.294 Mg m^−3
Mr = 280.32	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 5959 reflections
Hall symbol: I -4	θ = 2.9–27.5°
a = 24.758 (4) Å	µ = 0.09 mm^−1
c = 4.6952 (9) Å	T = 150 K
V = 2878.1 (8) Å^3	Block, colourless
Z = 8	0.20 × 0.10 × 0.10 mm
F(000) = 1184

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	1838 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
ϕ and ω scans	h = −32→32
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −32→32
Tmin = 0.983, Tmax = 0.991	l = −6→5
8208 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0339P)^2] where P = (Fo^2 + 2Fc^2)/3
1838 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.16 e Å^−3
4 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

17.1210 (0.0201) x + 0.9558 (0.0275) y + 3.3868 (0.0037) z = 1.0174 (0.0063)

* 0.0098 (0.0017) N1 * −0.0048 (0.0020) C2 * −0.0034 (0.0020) C3 * 0.0065 (0.0020) C4 * −0.0015 (0.0018) C4A * −0.0065 (0.0017) C9B

Rms deviation of fitted atoms = 0.0060

− 14.9176 (0.0246) x + 6.7625 (0.0306) y − 3.5209 (0.0037) z = 0.5527 (0.0111)

Angle to previous plane (with approximate e.s.d.) = 18.73 (0.14)

* −0.0032 (0.0019) C81 * 0.0019 (0.0019) C82 * 0.0023 (0.0020) C83 * 0.0003 (0.0021) C84 * −0.0012 (0.0022) C85 * −0.0001 (0.0021) C86

Rms deviation of fitted atoms = 0.0019

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.04022 (9)	0.26216 (9)	0.0260 (5)	0.0316 (6)
H1	−0.0452 (12)	0.2835 (12)	0.426 (7)	0.057 (11)*
C2	0.07861 (12)	0.26321 (13)	−0.1727 (7)	0.0399 (8)
H2	0.0899	0.2974	−0.2429	0.050*
C3	0.10310 (11)	0.21740 (13)	−0.2832 (7)	0.0399 (8)
H3	0.1305	0.2205	−0.4241	0.050*
C4	0.08743 (11)	0.16766 (12)	−0.1869 (7)	0.0366 (8)
H4	0.1042	0.1360	−0.2592	0.046*
C4A	0.04655 (10)	0.16353 (11)	0.0185 (6)	0.0311 (7)
C5	0.02781 (11)	0.11305 (11)	0.1295 (7)	0.0341 (7)
H5	0.0436	0.0805	0.0622	0.043*
C6	−0.01200 (10)	0.11030 (11)	0.3284 (7)	0.0332 (7)
H6	−0.0237	0.0763	0.3986	0.041*
C6A	−0.03598 (10)	0.15882 (10)	0.4307 (6)	0.0274 (7)
C7	−0.07682 (10)	0.17015 (10)	0.6335 (6)	0.0278 (7)
H7	−0.0968	0.1443	0.7396	0.035*
C8	−0.08244 (10)	0.22546 (10)	0.6493 (6)	0.0263 (6)
N9	−0.04610 (9)	0.24847 (10)	0.4606 (5)	0.0270 (6)
C9A	−0.01770 (10)	0.20845 (11)	0.3252 (6)	0.0268 (6)
C9B	0.02350 (10)	0.21262 (11)	0.1197 (6)	0.0277 (7)
C81	−0.11683 (10)	0.25757 (11)	0.8336 (6)	0.0286 (7)
C82	−0.10611 (11)	0.31220 (11)	0.8917 (7)	0.0366 (8)
H82	−0.0768	0.3298	0.7999	0.046*
C83	−0.16051 (11)	0.23337 (12)	0.9706 (7)	0.0359 (8)
H83	−0.1687	0.1966	0.9331	0.045*
C84	−0.13813 (13)	0.34066 (13)	1.0825 (7)	0.0461 (9)
H84	−0.1305	0.3776	1.1209	0.058*
C85	−0.18091 (14)	0.31576 (14)	1.2163 (7)	0.0487 (9)
H85	−0.2027	0.3354	1.3468	0.061*
C86	−0.19216 (12)	0.26215 (14)	1.1607 (7)	0.0447 (8)
H86	−0.2217	0.2450	1.2530	0.056*
O1W	0.00569 (10)	0.35901 (8)	0.2749 (5)	0.0458 (6)
H1W	0.0192 (12)	0.3296 (9)	0.205 (7)	0.057*
H2W	0.0023 (14)	0.3797 (11)	0.136 (5)	0.057*
O2W	0.00206 (9)	0.41992 (8)	−0.2372 (5)	0.0424 (6)
H3W	0.0275 (9)	0.4414 (10)	−0.228 (8)	0.053*
H4W	0.0047 (14)	0.4002 (11)	−0.384 (5)	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0285 (13)	0.0382 (14)	0.0281 (14)	−0.0063 (11)	−0.0052 (12)	0.0025 (12)
C2	0.0356 (17)	0.0506 (19)	0.0335 (19)	−0.0082 (15)	−0.0038 (17)	0.0070 (17)
C3	0.0285 (16)	0.060 (2)	0.0311 (17)	−0.0034 (15)	0.0030 (15)	−0.0033 (17)
C4	0.0293 (16)	0.0493 (19)	0.0312 (19)	0.0022 (14)	−0.0051 (15)	−0.0096 (17)
C4A	0.0242 (15)	0.0392 (17)	0.0298 (17)	0.0035 (13)	−0.0083 (15)	−0.0021 (15)
C5	0.0300 (16)	0.0323 (16)	0.040 (2)	0.0049 (13)	−0.0077 (16)	−0.0061 (16)
C6	0.0330 (16)	0.0279 (15)	0.0386 (18)	−0.0009 (13)	−0.0027 (16)	0.0012 (15)
C6A	0.0258 (15)	0.0285 (15)	0.0278 (17)	−0.0005 (12)	−0.0075 (13)	−0.0028 (13)
C7	0.0272 (15)	0.0280 (15)	0.0283 (17)	−0.0035 (12)	−0.0008 (14)	0.0025 (14)
C8	0.0233 (14)	0.0300 (15)	0.0255 (15)	−0.0001 (12)	−0.0073 (14)	0.0009 (14)
N9	0.0285 (13)	0.0257 (13)	0.0268 (14)	−0.0011 (11)	−0.0025 (11)	0.0007 (12)
C9A	0.0227 (14)	0.0297 (15)	0.0278 (15)	0.0018 (12)	−0.0074 (13)	−0.0013 (14)
C9B	0.0245 (14)	0.0363 (16)	0.0222 (16)	−0.0025 (12)	−0.0088 (13)	0.0001 (14)
C81	0.0308 (15)	0.0324 (16)	0.0227 (16)	0.0042 (13)	−0.0076 (14)	−0.0013 (14)
C82	0.0401 (17)	0.0352 (16)	0.0345 (19)	0.0071 (14)	−0.0070 (16)	0.0008 (15)
C83	0.0327 (16)	0.0377 (17)	0.0371 (19)	0.0038 (13)	−0.0027 (15)	−0.0004 (16)
C84	0.058 (2)	0.0399 (19)	0.040 (2)	0.0129 (17)	−0.0138 (19)	−0.0109 (17)
C85	0.050 (2)	0.059 (2)	0.037 (2)	0.0256 (19)	−0.0044 (19)	−0.0102 (18)
C86	0.0387 (18)	0.062 (2)	0.033 (2)	0.0122 (16)	0.0023 (16)	−0.0013 (19)
O1W	0.0617 (15)	0.0379 (14)	0.0379 (14)	0.0026 (12)	−0.0016 (12)	−0.0008 (11)
O2W	0.0496 (14)	0.0365 (14)	0.0412 (13)	−0.0047 (10)	0.0001 (12)	−0.0056 (12)

Geometric parameters (Å, º)

N1—C2	1.332 (4)	C8—C81	1.451 (4)
N1—C9B	1.367 (3)	N9—C9A	1.371 (3)
C2—C3	1.387 (4)	N9—H1	0.88 (3)
C2—H2	0.95	C9A—C9B	1.408 (4)
C3—C4	1.368 (4)	C81—C83	1.394 (4)
C3—H3	0.95	C81—C82	1.405 (4)
C4—C4A	1.402 (4)	C82—C84	1.388 (4)
C4—H4	0.95	C82—H82	0.95
C4A—C9B	1.424 (4)	C83—C86	1.385 (4)
C4A—C5	1.432 (4)	C83—H83	0.95
C5—C6	1.359 (4)	C84—C85	1.377 (4)
C5—H5	0.95	C84—H84	0.95
C6—C6A	1.423 (4)	C85—C86	1.381 (4)
C6—H6	0.95	C85—H85	0.95
C6A—C9A	1.400 (4)	C86—H86	0.95
C6A—C7	1.417 (4)	O1W—H1W	0.865 (17)
C7—C8	1.378 (3)	O1W—H2W	0.833 (18)
C7—H7	0.95	O2W—H3W	0.825 (17)
C8—N9	1.386 (3)	O2W—H4W	0.849 (18)
C2—N1—C9B	117.3 (2)	C9A—N9—H1	128 (2)
N1—C2—C3	123.9 (3)	C8—N9—H1	123 (2)
N1—C2—H2	118.0	N9—C9A—C6A	107.7 (2)
C3—C2—H2	118.0	N9—C9A—C9B	129.5 (3)
C4—C3—C2	119.2 (3)	C6A—C9A—C9B	122.8 (3)
C4—C3—H3	120.4	N1—C9B—C9A	120.4 (2)
C2—C3—H3	120.4	N1—C9B—C4A	122.5 (2)
C3—C4—C4A	119.8 (3)	C9A—C9B—C4A	117.2 (3)
C3—C4—H4	120.1	C83—C81—C82	118.1 (3)
C4A—C4—H4	120.1	C83—C81—C8	119.7 (2)
C4—C4A—C9B	117.2 (3)	C82—C81—C8	122.2 (3)
C4—C4A—C5	123.2 (3)	C84—C82—C81	120.4 (3)
C9B—C4A—C5	119.6 (3)	C84—C82—H82	119.8
C6—C5—C4A	121.9 (3)	C81—C82—H82	119.8
C6—C5—H5	119.0	C86—C83—C81	121.0 (3)
C4A—C5—H5	119.0	C86—C83—H83	119.5
C5—C6—C6A	119.5 (3)	C81—C83—H83	119.5
C5—C6—H6	120.3	C85—C84—C82	120.4 (3)
C6A—C6—H6	120.3	C85—C84—H84	119.8
C9A—C6A—C7	107.1 (2)	C82—C84—H84	119.8
C9A—C6A—C6	119.1 (3)	C86—C85—C84	119.9 (3)
C7—C6A—C6	133.7 (3)	C86—C85—H85	120.0
C8—C7—C6A	107.8 (2)	C84—C85—H85	120.0
C8—C7—H7	126.1	C85—C86—C83	120.2 (3)
C6A—C7—H7	126.1	C85—C86—H86	119.9
C7—C8—N9	108.0 (2)	C83—C86—H86	119.9
C7—C8—C81	129.5 (3)	H1W—O1W—H2W	105 (3)
N9—C8—C81	122.5 (2)	H3W—O2W—H4W	111 (3)
C9A—N9—C8	109.4 (2)
C9B—N1—C2—C3	−1.6 (4)	C2—N1—C9B—C9A	−178.7 (2)
N1—C2—C3—C4	0.3 (5)	C2—N1—C9B—C4A	1.7 (4)
C2—C3—C4—C4A	0.8 (4)	N9—C9A—C9B—N1	−0.5 (4)
C3—C4—C4A—C9B	−0.6 (4)	C6A—C9A—C9B—N1	−179.3 (2)
C3—C4—C4A—C5	179.9 (3)	N9—C9A—C9B—C4A	179.0 (3)
C4—C4A—C5—C6	−179.9 (3)	C6A—C9A—C9B—C4A	0.2 (4)
C9B—C4A—C5—C6	0.6 (4)	C4—C4A—C9B—N1	−0.7 (4)
C4A—C5—C6—C6A	0.0 (4)	C5—C4A—C9B—N1	178.9 (2)
C5—C6—C6A—C9A	−0.5 (4)	C4—C4A—C9B—C9A	179.8 (2)
C5—C6—C6A—C7	−179.3 (3)	C5—C4A—C9B—C9A	−0.7 (4)
C9A—C6A—C7—C8	−0.3 (3)	C7—C8—C81—C83	−17.8 (4)
C6—C6A—C7—C8	178.6 (3)	N9—C8—C81—C83	165.7 (3)
C6A—C7—C8—N9	0.1 (3)	C7—C8—C81—C82	158.8 (3)
C6A—C7—C8—C81	−176.8 (3)	N9—C8—C81—C82	−17.7 (4)
C7—C8—N9—C9A	0.2 (3)	C83—C81—C82—C84	0.6 (4)
C81—C8—N9—C9A	177.3 (2)	C8—C81—C82—C84	−176.1 (3)
C8—N9—C9A—C6A	−0.4 (3)	C82—C81—C83—C86	−0.6 (4)
C8—N9—C9A—C9B	−179.3 (3)	C8—C81—C83—C86	176.2 (3)
C7—C6A—C9A—N9	0.4 (3)	C81—C82—C84—C85	−0.2 (4)
C6—C6A—C9A—N9	−178.7 (2)	C82—C84—C85—C86	−0.1 (5)
C7—C6A—C9A—C9B	179.5 (2)	C84—C85—C86—C83	0.0 (5)
C6—C6A—C9A—C9B	0.3 (4)	C81—C83—C86—C85	0.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H1···O1W	0.88 (3)	2.36 (3)	3.145 (3)	148 (3)
O2W—H3W···O2W^i	0.83 (2)	1.99 (2)	2.807 (3)	168 (3)
O2W—H4W···O1W^ii	0.85 (2)	1.90 (2)	2.744 (3)	175 (3)
O1W—H1W···N1	0.87 (2)	1.94 (2)	2.801 (3)	172 (3)
O1W—H2W···O2W	0.83 (2)	2.02 (2)	2.840 (3)	170 (3)

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