4-Nitro­phenyl phenyl ether: sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S0108270105002076

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 3| March 2005| Pages o185-o187

doi:10.1107/S0108270105002076

4-Nitrophenyl phenyl ether: sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 18 January 2005; accepted 20 January 2005; online 28 February 2005)

In the title compound, C₁₂H₉NO₃, the ether C—O—C angle is 119.65 (10)°. The molecules are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, reinforced by an aromatic π–π stacking interaction.

Comment

We report here the molecular and supramolecular structure of the title compound, (I) (Fig. 1), a simple substituted analogue of the low-melting-point parent compound biphenyl ether, Ph₂O (m.p. ca 300 K), the structure of which does not appear in the Cambridge Structural Database (January 2005 release; Allen, 2002 ). The C—O distance to the substituted ring in (I) is significantly the shorter of the two C—O distances (Table 1), but the mean C—C distances for the two aryl rings are identical within experimental uncertainty. The C—O—C angle is strikingly larger than those typically found in water and simple ethers, which are just below the idealized tetrahedral value. The value of this angle in (I) may be compared with the corresponding C—O—C angle of 127.9 (1)° in Ph₃C—O—CPh₃ (Glidewell & Liles, 1978 ). Associated with this large angle is the concerted twist of the aryl rings away from the central C—O—C plane, as indicated by the relevant torsion angles. The dihedral angle between the ring planes is 63.2 (2)°. These geometric features are most readily ascribed to the avoidance of the mutual repulsion between the ortho H atoms bonded to atoms C2 and C16 (Fig. 1).

The molecules of (I) are linked into sheets by a combination of one C—H⋯O hydrogen bond and one C—H⋯π(arene) hydrogen bond, and these sheets are reinforced by an aromatic π–π stacking interaction. Aryl atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the molecule at (1 − x, y − $[{1\over 2}]$ , $[{1\over 2}]$ − z), so producing a C(6) (Bernstein et al., 1995 ) chain running parallel to the [010] direction and generated by the 2₁ screw axis along ( $[{1\over 2}]$ , y, $[{1\over 4}]$ ) (Fig. 2). A similar chain, antiparallel to the first and related to it by inversion, is generated by the 2₁ screw axis along ( $[{1\over 2}]$ , −y, $[{3\over 4}]$ ), and these chains are linked by the C—H⋯π(arene) hydrogen bond.

Aryl atom C2 in the molecule at (x, y, z), which forms part of the chain along ( $[{1\over 2}]$ , y, $[{1\over 4}]$ ), acts as hydrogen-bond donor to the unsubstituted C11–C16 ring in the molecule at (x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z), which lies in the chain along ( $[{1\over 2}]$ , −y, $[{3\over 4}]$ ). In this manner, a second chain motif is produced, running parallel to the [001] direction and generated by the c-glide plane at y = $[{1\over 4}]$ (Fig. 3). The combination of the [010] and [001] chains generates a (100) chain in the form of a (4,4)-net (Batten & Robson, 1998 ) built from a single type of ring (Fig. 4). Just one sheet of this type passes through each unit cell.

A single aromatic π–π stacking interaction reinforces the sheet. The C1–C6 rings in the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z) are strictly parallel and these molecules lie in the same sheet. The interplanar spacing between these molecules is 3.296 (2) Å and the ring–centroid separation is 3.695 (2) Å, corresponding to a centroid offset of 1.670 (2) Å (Fig. 5). There are no direction-specific interactions between adjacent (100) sheets.

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
Part of the crystal structure of (I

), showing the formation of a hydrogen-bonded chain along [010]. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 − x, y − $[{1\over 2}]$ , $[{1\over 2}]$ − z) and (1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z), respectively.

Figure 3
Part of the crystal structure of (I

), showing the formation of a hydrogen-bonded chain along [001]. Atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z), (x, y, 1 + z) and (x, $[{1\over 2}]$ − y, z − $[{1\over 2}]$ ), respectively.

Figure 4
A stereoview of part of the crystal structure of (I

), showing the formation of the (100) sheet.

Figure 5
Part of the crystal structure of (I

), showing the π–π stacking interaction. For the sake of clarity, H atoms have been omitted. The atom marked with an asterisk (*) is at the symmetry position (1 − x, 1 − y, 1 − z).

Experimental

A sample of the title compound was obtained from Aldrich. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Crystal data

C₁₂H₉NO₃
M_r = 215.20
Monoclinic, P 2₁ /c
a = 10.3300 (5) Å
b = 12.2408 (4) Å
c = 7.9804 (4) Å
β = 96.215 (2)°
V = 1003.17 (8) Å³
Z = 4
D_x = 1.425 Mg m⁻³
Mo Kα radiation
Cell parameters from 2285 reflections
θ = 3.1–27.5°
μ = 0.10 mm⁻¹
T = 120 (2) K
Shard, colourless
0.34 × 0.18 × 0.09 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.955, T_max = 0.991
11 250 measured reflections
2285 independent reflections
1644 reflections with I > 2σ(I)
R_int = 0.045
θ_max = 27.5°
h = −13 → 13
k = −15 → 15
l = −10 → 9

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.113
S = 1.04
2285 reflections
146 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0619P)² + 0.0313P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Extinction correction: SHELXL97 (Sheldrick, 1997 )
Extinction coefficient: 0.018 (3)

Table 1
Selected geometric parameters (Å, °)

O1—C1	1.3783 (15)
O1—C11	1.3955 (15)

C1—O1—C11	119.65 (10)

C2—C1—O1—C11	26.75 (19)
C1—O1—C11—C16	47.64 (18)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O42ⁱ	0.95	2.54	3.4033 (17)	152
C2—H2⋯Cgⁱⁱ	0.95	2.71	3.428 (2)	134
Symmetry codes: (i) $[1-x, y-{\script{1\over 2}}, {\script{1\over 2}}-z]$ ; (ii) $[x, {\script{1\over 2}}-y, z+{\script{1\over 2}}]$ .

The space group P2₁/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and with U_iso(H) = 1.2U_eq(C).

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL for Windows (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270105002076/sk1810sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105002076/sk1810Isup2.hkl

Comment top

We report here the molecular and supramolecular structure of the title compound, (I), (Fig. 1), a simple substituted analogue of the low-melting-point parent compound biphenyl ether, Ph₂O (m.p. ca 300 K), the structure of which does not appear in the January 2005 release of the Cambridge Structural Database (Allen, 2002). The C—O distance to the substituted ring in (I) is significantly the shorter of the two C—O distances (Table 1), but the mean C—C distances for the two aryl rings are identical within experimental uncertainty. The C—O—C angle is strikingly larger than those typically found in water and simple ethers, which are just below the idealized tetrahedral value. The value of this angle in (I) may be compared with the corresponding C—O—C angle of 127.9 (1)° in Ph₃C—O—CPh₃ (Glidewell & Liles, 1978). Associated with this large angle is the concerted twist of the aryl rings away from the central C—O—C plane, as indicated by the relevant torsional angles. The dihedral angle between the ring planes is 63.2 (2)°. These geometric features are most readily ascribed to the avoidance of the mutual repulsion between the ortho H atoms bonded to C2 and C16 (Fig. 1).

The molecules of (I) are linked into sheets by a combination of one C—H···O hydrogen bond and one C—H···π(arene) hydrogen bond, and these sheets are reinforced by an aromatic π–π stacking interaction. Aryl atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the molecule at (1 − x, y − 1/2, 1/2 − z), so producing a C(6) (Bernstein et al., 1995) chain running parallel to the [010] direction and generated by the 2₁ screw axis along (1/2, y, 1/4) (Fig. 2). A similar chain, antiparallel to the first and related to it by inversion, is generated by the 2₁ screw axis along (1/2, −y, 3/4), and these chains are linked by the C—H···π(arene) hydrogen bond.

Aryl atom C2 in the molecule at (x, y, z), which forms part of the chain along (1/2, y, 1/4), acts as hydrogen-bond donor to the unsubstituted C11–C16 ring in the molecule at (x, 1/2 − y, 1/2 + z), which lies in the chain along (1/2, −y, 3/4). In this manner, a second chain motif is produced, running parallel to the [001] direction and generated by the c-glide plane at y = 1/4 (Fig. 3). The combination of the [010] and [001] chains generates a (100) chain in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of ring (Fig. 4). Just one sheet of this type passes through each unit cell.

Experimental top

A sample of the title compound was obtained from Aldrich. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of(I), showing the formation of a hydrogen-bonded chain along [010]. The atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 − x, y − 1/2, 1/2 − z) and (1 − x, 1/2 + y, 1/2 − z), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain along [001]. The atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (x, 1/2 − y, 1/2 + z), (x, y, 1 + z) and (x, 1/2 − y, z − 1/2), respectively.
	Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of the (100) sheet.
	Fig. 5. Part of the crystal structure of (I), showing the π–π stacking interaction. For the sake of clarity, H atoms have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).

4-Nitrophenyl phenyl ether top

Crystal data top

C₁₂H₉NO₃	F(000) = 448
M_r = 215.20	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2285 reflections
a = 10.3300 (5) Å	θ = 3.1–27.5°
b = 12.2408 (4) Å	µ = 0.10 mm⁻¹
c = 7.9804 (4) Å	T = 120 K
β = 96.215 (2)°	Shard, colourless
V = 1003.17 (8) Å³	0.34 × 0.18 × 0.09 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	2285 independent reflections
Graphite monochromator	1644 reflections with I > 2σ(I)
Detector resolution: 9.091 pixels mm^-1	R_int = 0.045
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
T_min = 0.955, T_max = 0.991	k = −15→15
11250 measured reflections	l = −10→9

Refinement top

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0619P)² + 0.0313P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2285 reflections	Δρ_max = 0.22 e Å⁻³
146 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₁₂H₉NO₃	V = 1003.17 (8) Å³
M_r = 215.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3300 (5) Å	µ = 0.10 mm⁻¹
b = 12.2408 (4) Å	T = 120 K
c = 7.9804 (4) Å	0.34 × 0.18 × 0.09 mm
β = 96.215 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2285 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1644 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.991	R_int = 0.045
11250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
2285 reflections	Δρ_min = −0.29 e Å⁻³
146 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.36142 (9)	0.31179 (7)	0.32222 (13)	0.0236 (3)
O41	0.22322 (10)	0.78372 (8)	0.54552 (14)	0.0310 (3)
O42	0.38921 (10)	0.81782 (8)	0.41061 (15)	0.0325 (3)
N4	0.31209 (11)	0.75386 (9)	0.46511 (16)	0.0224 (3)
C1	0.34314 (12)	0.42031 (10)	0.35927 (17)	0.0193 (3)
C2	0.25253 (12)	0.45470 (11)	0.46435 (18)	0.0215 (3)
C3	0.24360 (13)	0.56507 (11)	0.50037 (18)	0.0214 (3)
C4	0.32547 (12)	0.63742 (10)	0.43173 (17)	0.0195 (3)
C5	0.41804 (12)	0.60360 (11)	0.32985 (18)	0.0210 (3)
C6	0.42682 (12)	0.49404 (11)	0.29330 (18)	0.0204 (3)
C11	0.25903 (12)	0.23800 (10)	0.32812 (18)	0.0200 (3)
C12	0.28895 (14)	0.13855 (11)	0.40378 (17)	0.0224 (3)
C13	0.19265 (14)	0.05949 (11)	0.40325 (18)	0.0265 (4)
C14	0.06804 (14)	0.08090 (12)	0.32944 (19)	0.0280 (4)
C15	0.03923 (14)	0.18169 (12)	0.25384 (19)	0.0262 (4)
C16	0.13495 (13)	0.26051 (11)	0.25177 (19)	0.0234 (3)
H2	0.1974	0.4034	0.5109	0.026*
H3	0.1819	0.5905	0.5714	0.026*
H5	0.4745	0.6550	0.2859	0.025*
H6	0.4896	0.4690	0.2235	0.024*
H12	0.3745	0.1243	0.4556	0.027*
H13	0.2125	−0.0096	0.4538	0.032*
H14	0.0021	0.0269	0.3303	0.034*
H15	−0.0466	0.1964	0.2034	0.031*
H16	0.1159	0.3290	0.1988	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0204 (5)	0.0176 (5)	0.0334 (6)	−0.0013 (4)	0.0060 (4)	−0.0014 (4)
O41	0.0293 (5)	0.0258 (6)	0.0397 (7)	0.0011 (4)	0.0114 (5)	−0.0047 (5)
O42	0.0318 (6)	0.0213 (5)	0.0458 (7)	−0.0067 (4)	0.0104 (5)	0.0031 (5)
N4	0.0210 (6)	0.0210 (6)	0.0251 (7)	−0.0015 (5)	0.0015 (5)	0.0014 (5)
C1	0.0191 (6)	0.0178 (7)	0.0204 (8)	0.0005 (5)	−0.0009 (6)	0.0003 (5)
C2	0.0215 (7)	0.0208 (7)	0.0227 (8)	−0.0025 (5)	0.0041 (6)	0.0032 (6)
C3	0.0193 (7)	0.0246 (7)	0.0204 (8)	0.0018 (5)	0.0033 (6)	0.0017 (6)
C4	0.0200 (7)	0.0170 (7)	0.0206 (8)	0.0011 (5)	−0.0015 (6)	−0.0003 (6)
C5	0.0187 (6)	0.0230 (7)	0.0209 (8)	−0.0030 (6)	0.0000 (6)	0.0042 (6)
C6	0.0172 (6)	0.0237 (7)	0.0204 (8)	−0.0003 (5)	0.0028 (6)	−0.0003 (6)
C11	0.0208 (7)	0.0186 (7)	0.0214 (8)	−0.0022 (5)	0.0063 (6)	−0.0027 (5)
C12	0.0238 (7)	0.0231 (7)	0.0204 (8)	0.0039 (6)	0.0035 (6)	−0.0005 (6)
C13	0.0383 (9)	0.0185 (7)	0.0238 (9)	0.0009 (6)	0.0086 (7)	0.0007 (6)
C14	0.0300 (8)	0.0251 (8)	0.0303 (9)	−0.0081 (6)	0.0104 (7)	−0.0064 (6)
C15	0.0215 (7)	0.0288 (8)	0.0283 (9)	−0.0020 (6)	0.0034 (6)	−0.0038 (6)
C16	0.0250 (7)	0.0225 (7)	0.0231 (8)	0.0024 (6)	0.0042 (6)	0.0003 (6)

Geometric parameters (Å, º) top

O1—C1	1.3783 (15)	N4—O41	1.2311 (15)
C1—C2	1.3880 (19)	O1—C11	1.3955 (15)
C1—C6	1.3919 (19)	C11—C12	1.3790 (18)
C2—C3	1.3864 (19)	C11—C16	1.3860 (19)
C2—H2	0.95	C12—C13	1.3875 (19)
C3—C4	1.3784 (19)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.382 (2)
C4—C5	1.3839 (19)	C13—H13	0.95
C4—N4	1.4593 (17)	C14—C15	1.391 (2)
C5—C6	1.3775 (19)	C14—H14	0.95
C5—H5	0.95	C15—C16	1.3829 (19)
C6—H6	0.95	C15—H15	0.95
N4—O42	1.2296 (15)	C16—H16	0.95

O1—C1—C2	122.61 (12)	O41—N4—C4	118.41 (11)
O1—C1—C6	116.02 (12)	C1—O1—C11	119.65 (10)
C2—C1—C6	121.26 (12)	C12—C11—C16	121.39 (13)
C3—C2—C1	119.02 (12)	C12—C11—O1	116.83 (12)
C3—C2—H2	120.5	C16—C11—O1	121.65 (12)
C1—C2—H2	120.5	C11—C12—C13	119.19 (13)
C4—C3—C2	119.10 (13)	C11—C12—H12	120.4
C4—C3—H3	120.4	C13—C12—H12	120.4
C2—C3—H3	120.4	C14—C13—C12	120.24 (13)
C3—C4—C5	122.27 (12)	C14—C13—H13	119.9
C3—C4—N4	118.73 (12)	C12—C13—H13	119.9
C5—C4—N4	118.98 (12)	C13—C14—C15	119.92 (13)
C6—C5—C4	118.76 (12)	C13—C14—H14	120.0
C6—C5—H5	120.6	C15—C14—H14	120.0
C4—C5—H5	120.6	C16—C15—C14	120.28 (13)
C5—C6—C1	119.56 (13)	C16—C15—H15	119.9
C5—C6—H6	120.2	C14—C15—H15	119.9
C1—C6—H6	120.2	C15—C16—C11	118.97 (13)
O42—N4—O41	122.93 (11)	C15—C16—H16	120.5
O42—N4—C4	118.65 (11)	C11—C16—H16	120.5

O1—C1—C2—C3	177.57 (11)	C5—C4—N4—O41	174.73 (12)
C6—C1—C2—C3	1.6 (2)	C2—C1—O1—C11	26.75 (19)
C1—C2—C3—C4	−0.4 (2)	C6—C1—O1—C11	−157.09 (12)
C2—C3—C4—C5	−1.0 (2)	C1—O1—C11—C12	−136.55 (13)
C2—C3—C4—N4	177.71 (12)	C1—O1—C11—C16	47.64 (18)
C3—C4—C5—C6	1.3 (2)	C16—C11—C12—C13	0.0 (2)
N4—C4—C5—C6	−177.47 (11)	O1—C11—C12—C13	−175.80 (12)
C4—C5—C6—C1	−0.1 (2)	C11—C12—C13—C14	−0.8 (2)
O1—C1—C6—C5	−177.58 (12)	C12—C13—C14—C15	0.6 (2)
C2—C1—C6—C5	−1.4 (2)	C13—C14—C15—C16	0.2 (2)
C3—C4—N4—O42	176.54 (12)	C14—C15—C16—C11	−0.9 (2)
C5—C4—N4—O42	−4.66 (19)	C12—C11—C16—C15	0.8 (2)
C3—C4—N4—O41	−4.06 (19)	O1—C11—C16—C15	176.43 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O42ⁱ	0.95	2.54	3.4033 (17)	152
C2—H2···Cgⁱⁱ	0.95	2.71	3.428 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₃
M_r	215.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.3300 (5), 12.2408 (4), 7.9804 (4)
β (°)	96.215 (2)
V (Å³)	1003.17 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.18 × 0.09

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.955, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	11250, 2285, 1644
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.113, 1.04
No. of reflections	2285
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

O1—C1	1.3783 (15)	O1—C11	1.3955 (15)

C1—O1—C11	119.65 (10)

C2—C1—O1—C11	26.75 (19)	C1—O1—C11—C16	47.64 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O42ⁱ	0.95	2.54	3.4033 (17)	152
C2—H2···Cgⁱⁱ	0.95	2.71	3.428 (2)	134

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

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JLW thanks CNPq and FAPERJ for financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494. Web of Science CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Glidewell, C. & Liles, D. C. (1978). Acta Cryst. B34, 696–698. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2053-2296

Volume 61| Part 3| March 2005| Pages o185-o187

doi:10.1107/S0108270105002076

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Nitro­phenyl phenyl ether: sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Nitrophenyl phenyl ether: sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds