Acridine 0.75-hydrate

Schur, E.; Bernstein, J.; Lemmerer, A.; Vainer, R.

doi:10.1107/S1600536811038220

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2761

https://doi.org/10.1107/S1600536811038220

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Acridine 0.75-hydrate

Einat Schur,^a ^* Joel Bernstein,^a Andreas Lemmerer ^a and Radion Vainer ^a

^aBen Gurion University of the Negev, Beer Sheva, Israel 84105
^*Correspondence e-mail: schur@bgu.ac.il

(Received 29 June 2011; accepted 19 September 2011; online 30 September 2011)

The title compound, C₁₃H₉N·0.75H₂O was obtained during a study of the polymorphic system of acridine, by slow evaporation from an ethanol–water solution. There are two acridine molecules (indicated by I and II, respectively) and one and a half water molecules in the asymmetric unit. The half-molecule of water is located on a crystallographic twofold axis. The crystal structure is built up from two threads of molecule II sewn together with water molecules through O—H⋯O and O—H⋯N hydrogen bonds from one side and with π–π interactions [centroid–centroid distance = 3.640 (3) and 3.7431 (3) Å] between overlapping molecules II on the other side. Molecule I is attached to this thread from both sides by C—H⋯O hydrogen bonds. The threads are connected to each other by π–π interactions [centroid–centroid distances = 3.582 (3) and 3.582 (3) Å] between the inner side of molecule I and stabilized by a C—H⋯π interaction on the other side of molecule I. This thread with rows of molecule I hanging on its sides is generated by translation perpendicular to the a axis.

Related literature

For the five anhydrous polymorphs of acridine, see: Phillips (1954 , 1956 ), Phillips et al. (1960 ) and Mei & Wolf (2004 ) for monoclinic forms VI and VII, and Braga et al. (2010 ) for orthorhombic form IV and monoclinic forms II and III. For further crystallographic studies of acridine hydrate, see: Groth (1919 ); Lowde et al. (1953 ).

Experimental

Crystal data

C₁₃H₉N·0.75H₂O
M_r = 192.71
Orthorhombic, P b c n
a = 26.400 (5) Å
b = 8.893 (5) Å
c = 17.492 (5) Å
V = 4107 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 197 K
0.3 × 0.3 × 0.3 mm

Data collection

Bruker SMART 6000 diffractometer
14504 measured reflections
3606 independent reflections
1733 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.197
S = 1.00
3606 reflections
272 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C6–C8/C13/N1 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N2	0.933 (3)	1.942 (2)	2.873 (4)	175.2 (2)
C7—H7⋯O1	0.93	2.35	3.271 (4)	171
O1—H1⋯O2ⁱ	0.95 (1)	1.98 (5)	2.777 (4)	139 (6)
C16—H16⋯Cg1ⁱⁱ	0.93	2.93	3.773 (5)	152
C18—H18⋯Cg2ⁱⁱⁱ	0.93	2.93	3.848 (5)	168
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811038220/ez2255sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038220/ez2255Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038220/ez2255Isup3.cml

checkCIF report

Comment top

Acridine hydrate is the hydrated form of the very rich polymorphic system of acridine. There are five anhydrous polymorphs of acridine with fully analyzed structures: an orthorhombic form and four monoclinic forms. For the orthorhombic form (form IV) cell parameters were first published by Phillips (1954), and the full solution was recently published by Braga et al. (2010). The monoclinic forms are designated II, III, VI and VII. The crystal structure of forms III and II respectively were determined by Phillips (1956) and Phillips et al. (1960) and redetermined by Mei and Wolf (2004) and by Braga et al. (2010). Forms VI and VII were reported by Mei and Wolf (2004). The form described in this paper was initially thought to be one of the first polymorphs of acridine and known historically as the orthorhombic form of Groth (1919) and subsequently labeled as acridine I. Lowde et al. (1953) established the unit cell parameters, the space group and the density. From analysis using the Karl Fischer reagent, it was concluded that acridine I is in fact the monohydrate and not a polymorph of acridine.

There are two acridine molecules and one and a half water molecules in the asymmetric unit (see Fig. 1). In the packing diagram (see Fig. 2), molecule I is colored in green, molecule II is colored in blue, the water molecule that is sitting on a two fold axis is red and the other one is in yellow. The molecules are linked by O—H···O and C—H···O hydrogen bonds (see Table 1).

Related literature top

For the five anhydrous polymorphs of acridine, see: Phillips (1954, 1956), Phillips et al. (1960) and Mei & Wolf (2004) for monoclinic forms VI and VII, and Braga et al. (2010) for orthorhombic form IV and monoclinic forms II and III. For further crystallographic studies of acridine hydrate, see: Groth (1919); Lowde et al. (1953).

Experimental top

The title compound was obtained by slow evaporation from an ethanol-water solution in 3:1 and 2:1 ratio at 4°C. The crystals are unstable at room temperature and transform to the anhydrous form III. The common habit of acridine hydrate is thick yellow needles but other habits may be obtained as well.

Structure description top

For the five anhydrous polymorphs of acridine, see: Phillips (1954, 1956), Phillips et al. (1960) and Mei & Wolf (2004) for monoclinic forms VI and VII, and Braga et al. (2010) for orthorhombic form IV and monoclinic forms II and III. For further crystallographic studies of acridine hydrate, see: Groth (1919); Lowde et al. (1953).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al.,2009); software used to prepare material for publication: OLEX2 (Dolomanov et al.,2009).

Figures top

	Fig. 1. The asymmetric unit with atom labels and 50% probability displacement ellipsoids for non-H atoms. Atom H1ⁱ is generated by a two-fold axis (-x, y, -z-1/2).
	Fig. 2. The packing of acridine hydrate viewed down the b axis. Hydrogen bonds are marked in dashed lines.

Acridine 0.75-hydrate top

Crystal data top

C₁₃H₉N·0.75H₂O	F(000) = 1632
M_r = 192.71	D_x = 1.247 Mg m⁻³ D_m = 1.247 Mg m⁻³ D_m measured by not measured
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1764 reflections
a = 26.400 (5) Å	θ = 2.3–21.8°
b = 8.893 (5) Å	µ = 0.08 mm⁻¹
c = 17.492 (5) Å	T = 197 K
V = 4107 (3) Å³	Cube, yellow
Z = 16	0.3 × 0.3 × 0.3 mm

Data collection top

Bruker SMART 6000 diffractometer	1733 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 3.3°
phi and ω scans	h = −31→22
14504 measured reflections	k = −10→9
3606 independent reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0837P)² + 1.779P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max = 0.035
272 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₉N·0.75H₂O	V = 4107 (3) Å³
M_r = 192.71	Z = 16
Orthorhombic, Pbcn	Mo Kα radiation
a = 26.400 (5) Å	µ = 0.08 mm⁻¹
b = 8.893 (5) Å	T = 197 K
c = 17.492 (5) Å	0.3 × 0.3 × 0.3 mm

Data collection top

Bruker SMART 6000 diffractometer	1733 reflections with I > 2σ(I)
14504 measured reflections	R_int = 0.068
3606 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	2 restraints
wR(F²) = 0.197	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.35 e Å⁻³
3606 reflections	Δρ_min = −0.29 e Å⁻³
272 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.08797 (12)	0.6902 (4)	−0.0316 (2)	0.0579 (9)
C2	0.10417 (14)	0.8419 (5)	−0.0350 (2)	0.0746 (11)
H2	0.1166	0.8883	0.0088	0.090*
C3	0.10180 (15)	0.9206 (5)	−0.1017 (3)	0.0846 (13)
H3	0.1125	1.0202	−0.1031	0.102*
C4	0.08311 (15)	0.8515 (6)	−0.1688 (3)	0.0839 (13)
H4	0.0813	0.9066	−0.2140	0.101*
C5	0.06791 (14)	0.7066 (5)	−0.1681 (2)	0.0741 (11)
H5	0.0563	0.6625	−0.2130	0.089*
C6	0.06934 (11)	0.6201 (5)	−0.0995 (2)	0.0581 (9)
C7	0.05310 (11)	0.4738 (4)	−0.09624 (19)	0.0551 (9)
H7	0.0409	0.4271	−0.1401	0.066*
C8	0.05470 (11)	0.3952 (4)	−0.0281 (2)	0.0571 (9)
C9	0.03850 (13)	0.2431 (5)	−0.0214 (2)	0.0703 (11)
H9	0.0268	0.1922	−0.0644	0.084*
C10	0.03996 (14)	0.1718 (5)	0.0472 (3)	0.0789 (12)
H10	0.0293	0.0724	0.0507	0.095*
C11	0.05760 (14)	0.2473 (6)	0.1135 (2)	0.0798 (12)
H11	0.0583	0.1969	0.1601	0.096*
C12	0.07325 (13)	0.3910 (5)	0.1097 (2)	0.0689 (11)
H12	0.0843	0.4392	0.1538	0.083*
C13	0.07305 (11)	0.4701 (4)	0.0390 (2)	0.0578 (9)
C14	0.19756 (12)	0.7990 (4)	0.28030 (18)	0.0503 (8)
C15	0.16763 (13)	0.7107 (4)	0.3315 (2)	0.0628 (10)
H15	0.1325	0.7115	0.3271	0.075*
C16	0.18986 (15)	0.6257 (4)	0.3863 (2)	0.0716 (11)
H16	0.1697	0.5686	0.4189	0.086*
C17	0.24310 (16)	0.6224 (4)	0.3950 (2)	0.0708 (11)
H17	0.2577	0.5645	0.4334	0.085*
C18	0.27294 (14)	0.7039 (4)	0.3470 (2)	0.0638 (10)
H18	0.3079	0.7009	0.3530	0.077*
C19	0.25146 (12)	0.7941 (4)	0.28769 (18)	0.0514 (8)
C20	0.28036 (11)	0.8773 (4)	0.23658 (18)	0.0524 (8)
H20	0.3155	0.8749	0.2398	0.063*
C21	0.25709 (12)	0.9640 (4)	0.18072 (18)	0.0504 (8)
C22	0.28402 (14)	1.0520 (4)	0.1261 (2)	0.0639 (10)
H22	0.3192	1.0524	0.1271	0.077*
C23	0.25950 (17)	1.1351 (4)	0.0727 (2)	0.0737 (11)
H23	0.2779	1.1914	0.0376	0.088*
C24	0.20596 (17)	1.1363 (4)	0.0705 (2)	0.0734 (11)
H24	0.1893	1.1932	0.0336	0.088*
C25	0.17860 (13)	1.0551 (4)	0.1217 (2)	0.0632 (10)
H25	0.1434	1.0584	0.1199	0.076*
C26	0.20288 (12)	0.9648 (4)	0.17826 (18)	0.0514 (8)
N1	0.08930 (10)	0.6160 (4)	0.03670 (17)	0.0675 (9)
N2	0.17409 (9)	0.8829 (3)	0.22676 (15)	0.0528 (7)
O1	0.0000	0.3361 (6)	−0.2500	0.1183 (16)
O2	0.07381 (11)	0.8227 (5)	0.17081 (17)	0.1234 (14)
H2A	0.0499	0.9004	0.2031	0.137 (18)*
H2B	0.1071	0.8385	0.1869	0.137 (18)*
H1	−0.0308 (14)	0.280 (6)	−0.248 (4)	0.205*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (18)	0.066 (2)	0.064 (2)	0.0044 (17)	0.0016 (16)	−0.010 (2)
C2	0.065 (2)	0.075 (3)	0.084 (3)	−0.003 (2)	0.015 (2)	−0.021 (3)
C3	0.074 (3)	0.071 (3)	0.110 (3)	−0.002 (2)	0.029 (3)	−0.009 (3)
C4	0.077 (3)	0.095 (4)	0.080 (3)	0.006 (3)	0.017 (2)	0.008 (3)
C5	0.066 (2)	0.093 (3)	0.064 (2)	−0.002 (2)	0.0025 (18)	−0.005 (2)
C6	0.0389 (17)	0.073 (3)	0.063 (2)	0.0082 (17)	0.0009 (15)	−0.012 (2)
C7	0.0434 (18)	0.068 (2)	0.054 (2)	0.0046 (18)	−0.0042 (15)	−0.0172 (19)
C8	0.0383 (17)	0.062 (2)	0.071 (2)	0.0124 (17)	−0.0010 (16)	−0.016 (2)
C9	0.056 (2)	0.069 (3)	0.086 (3)	0.005 (2)	0.0002 (19)	−0.016 (2)
C10	0.058 (2)	0.067 (3)	0.112 (3)	0.011 (2)	0.010 (2)	0.003 (3)
C11	0.060 (2)	0.097 (4)	0.082 (3)	0.017 (2)	−0.002 (2)	0.010 (3)
C12	0.053 (2)	0.086 (3)	0.068 (3)	0.010 (2)	−0.0068 (18)	−0.003 (2)
C13	0.0365 (17)	0.071 (3)	0.066 (2)	0.0093 (17)	−0.0025 (15)	−0.011 (2)
C14	0.0470 (18)	0.047 (2)	0.0574 (19)	0.0011 (16)	0.0037 (16)	−0.0130 (17)
C15	0.054 (2)	0.063 (2)	0.072 (2)	−0.0028 (19)	0.0115 (18)	−0.010 (2)
C16	0.087 (3)	0.059 (3)	0.069 (2)	−0.006 (2)	0.013 (2)	−0.003 (2)
C17	0.087 (3)	0.063 (3)	0.063 (2)	0.002 (2)	−0.008 (2)	−0.003 (2)
C18	0.063 (2)	0.063 (2)	0.066 (2)	0.008 (2)	−0.0122 (19)	−0.009 (2)
C19	0.0486 (18)	0.049 (2)	0.0570 (19)	0.0012 (16)	−0.0049 (16)	−0.0135 (18)
C20	0.0380 (17)	0.054 (2)	0.065 (2)	−0.0018 (16)	−0.0014 (15)	−0.0157 (19)
C21	0.0512 (18)	0.0441 (19)	0.0560 (19)	−0.0004 (16)	0.0004 (16)	−0.0157 (17)
C22	0.064 (2)	0.061 (2)	0.066 (2)	−0.0080 (19)	0.0095 (19)	−0.014 (2)
C23	0.099 (3)	0.058 (3)	0.065 (2)	−0.011 (2)	0.011 (2)	−0.005 (2)
C24	0.095 (3)	0.059 (2)	0.066 (2)	−0.001 (2)	−0.015 (2)	−0.005 (2)
C25	0.060 (2)	0.057 (2)	0.073 (2)	0.0022 (19)	−0.0128 (19)	−0.011 (2)
C26	0.0475 (18)	0.047 (2)	0.060 (2)	0.0032 (16)	−0.0039 (16)	−0.0153 (18)
N1	0.0478 (16)	0.082 (2)	0.073 (2)	0.0054 (16)	−0.0043 (14)	−0.0156 (19)
N2	0.0406 (15)	0.0505 (17)	0.0672 (17)	0.0005 (13)	−0.0006 (13)	−0.0101 (15)
O1	0.077 (3)	0.118 (4)	0.160 (4)	0.000	0.014 (3)	0.000
O2	0.0619 (18)	0.204 (4)	0.104 (2)	−0.034 (2)	−0.0056 (17)	−0.013 (3)

Geometric parameters (Å, º) top

C1—C2	1.416 (5)	C14—N2	1.348 (4)
C1—C6	1.430 (5)	C15—H15	0.9300
C1—N1	1.365 (4)	C15—C16	1.354 (5)
C2—H2	0.9300	C16—H16	0.9300
C2—C3	1.362 (5)	C16—C17	1.414 (5)
C3—H3	0.9300	C17—H17	0.9300
C3—C4	1.414 (6)	C17—C18	1.359 (5)
C4—H4	0.9300	C18—H18	0.9300
C4—C5	1.350 (6)	C18—C19	1.429 (4)
C5—H5	0.9300	C19—C20	1.389 (4)
C5—C6	1.425 (5)	C20—H20	0.9300
C6—C7	1.371 (5)	C20—C21	1.388 (4)
C7—H7	0.9300	C21—C22	1.425 (5)
C7—C8	1.382 (5)	C21—C26	1.432 (4)
C8—C9	1.423 (5)	C22—H22	0.9300
C8—C13	1.434 (5)	C22—C23	1.356 (5)
C9—H9	0.9300	C23—H23	0.9300
C9—C10	1.358 (5)	C23—C24	1.414 (5)
C10—H10	0.9300	C24—H24	0.9300
C10—C11	1.420 (5)	C24—C25	1.359 (5)
C11—H11	0.9300	C25—H25	0.9300
C11—C12	1.345 (6)	C25—C26	1.426 (4)
C12—H12	0.9300	C26—N2	1.352 (4)
C12—C13	1.423 (5)	O1—H1	0.954 (11)
C13—N1	1.367 (5)	O2—H2A	1.093 (4)
C14—C15	1.430 (5)	O2—H2B	0.933 (3)
C14—C19	1.430 (4)

C2—C1—C6	118.9 (4)	N2—C14—C19	122.5 (3)
N1—C1—C2	119.3 (3)	C14—C15—H15	119.7
N1—C1—C6	121.7 (3)	C16—C15—C14	120.7 (3)
C1—C2—H2	119.6	C16—C15—H15	119.7
C3—C2—C1	120.8 (4)	C15—C16—H16	119.4
C3—C2—H2	119.6	C15—C16—C17	121.2 (4)
C2—C3—H3	119.9	C17—C16—H16	119.4
C2—C3—C4	120.3 (4)	C16—C17—H17	120.0
C4—C3—H3	119.9	C18—C17—C16	119.9 (4)
C3—C4—H4	119.6	C18—C17—H17	120.0
C5—C4—C3	120.7 (4)	C17—C18—H18	119.4
C5—C4—H4	119.6	C17—C18—C19	121.2 (3)
C4—C5—H5	119.5	C19—C18—H18	119.4
C4—C5—C6	121.0 (4)	C18—C19—C14	118.5 (3)
C6—C5—H5	119.5	C20—C19—C14	118.2 (3)
C5—C6—C1	118.3 (4)	C20—C19—C18	123.3 (3)
C7—C6—C1	119.1 (3)	C19—C20—H20	119.8
C7—C6—C5	122.6 (3)	C21—C20—C19	120.4 (3)
C6—C7—H7	119.8	C21—C20—H20	119.8
C6—C7—C8	120.4 (3)	C20—C21—C22	123.8 (3)
C8—C7—H7	119.8	C20—C21—C26	117.8 (3)
C7—C8—C9	122.8 (3)	C22—C21—C26	118.4 (3)
C7—C8—C13	118.8 (3)	C21—C22—H22	119.2
C9—C8—C13	118.4 (4)	C23—C22—C21	121.5 (3)
C8—C9—H9	119.7	C23—C22—H22	119.2
C10—C9—C8	120.5 (4)	C22—C23—H23	120.0
C10—C9—H9	119.7	C22—C23—C24	120.0 (4)
C9—C10—H10	119.6	C24—C23—H23	120.0
C9—C10—C11	120.7 (4)	C23—C24—H24	119.7
C11—C10—H10	119.6	C25—C24—C23	120.6 (4)
C10—C11—H11	119.7	C25—C24—H24	119.7
C12—C11—C10	120.6 (4)	C24—C25—H25	119.4
C12—C11—H11	119.7	C24—C25—C26	121.2 (3)
C11—C12—H12	119.6	C26—C25—H25	119.4
C11—C12—C13	120.8 (4)	C25—C26—C21	118.2 (3)
C13—C12—H12	119.6	N2—C26—C21	122.7 (3)
C12—C13—C8	118.9 (4)	N2—C26—C25	119.1 (3)
N1—C13—C8	121.5 (3)	C13—N1—C1	118.5 (3)
N1—C13—C12	119.6 (3)	C14—N2—C26	118.4 (3)
C19—C14—C15	118.5 (3)	H2A—O2—H2B	107.1 (3)
N2—C14—C15	119.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C6–C8/C13/N1 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N2	0.933 (3)	1.942 (2)	2.873 (4)	175.2 (2)
C7—H7···O1	0.93	2.35	3.271 (4)	171
O1—H1···O2ⁱ	0.95 (1)	1.98 (5)	2.777 (4)	139 (6)
C16—H16···Cg1ⁱⁱ	0.93	2.93	3.773 (5)	152
C18—H18···Cg2ⁱⁱⁱ	0.93	2.93	3.848 (5)	168

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N·0.75H₂O
M_r	192.71
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	197
a, b, c (Å)	26.400 (5), 8.893 (5), 17.492 (5)
V (Å³)	4107 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.3 × 0.3

Data collection
Diffractometer	Bruker SMART 6000
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14504, 3606, 1733
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.197, 1.00
No. of reflections	3606
No. of parameters	272
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al.,2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C6–C8/C13/N1 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N2	0.933 (3)	1.942 (2)	2.873 (4)	175.2 (2)
C7—H7···O1	0.93	2.35	3.271 (4)	171.2
O1—H1···O2ⁱ	0.954 (11)	1.98 (5)	2.777 (4)	139 (6)
C16—H16···Cg1ⁱⁱ	0.93	2.93	3.773 (5)	152
C18—H18···Cg2ⁱⁱⁱ	0.93	2.93	3.848 (5)	168

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+3/2, z+1/2.

References

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