3,4-Dichloro-1-nitro­benzene–aniline (2/1)

Barnett, S.A.; Johnston, A.; Florence, A.J.; Kennedy, A.R.

doi:10.1107/S1600536805019999

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 7| July 2005| Pages o2318-o2319

https://doi.org/10.1107/S1600536805019999

3,4-Dichloro-1-nitrobenzene–aniline (2/1)

Sarah A. Barnett,^a ^* Andrea Johnston,^b Alastair J. Florence ^b and Alan R. Kennedy ^c

^aDepartment of Theoretical and Computational Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, England, ^bDepartment of Pharmaceutical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland, and ^cDepartment of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
^*Correspondence e-mail: sarah.barnett@ucl.ac.uk

(Received 22 June 2005; accepted 24 June 2005; online 30 June 2005)

The solvate structure of 3,4-dichloro-1-nitrobenzene with aniline, 2C₆H₃Cl₂NO₂·C₆H₇N, is reported. Ribbons of 3,4-dichloronitrobenzene, formed by Cl⋯Cl and N—O⋯Cl interactions, are linked together via N—H⋯O hydrogen bonds with aniline into an undulating two-dimensional sheet.

Comment

The title compound, (I), was produced during an automated parallel crystallization polymorph screen on 3,4-dichloronitrobenzene (3,4-DCNB). The sample was identified as a novel form using multi-sample X-ray powder diffraction analysis of all recrystallized samples (Florence et al., 2003 ). Subsequent manual recrystallization from a saturated aniline solution by slow evaporation at 298 K yielded samples suitable for single-crystal X-ray analysis. The title solvate, (I), crystallizes in the space group P2₁/n with two molecules of 3,4-DCNB and one molecule of aniline in the asymmetric unit (Fig. 1).

The crystal structure of (I) is characterized by ribbons of 3,4-DCNB, which are linked by aniline molecules to form a continuous sheet (Fig. 2). Molecules of type 1 (C1–C6) form a zigzag chain via Cl⋯Cl interactions [Cl1⋯Cl2ⁱ = 3.399 (1) Å and C3—Cl1⋯Cl2ⁱ = 149.4 (1)°; symmetry code: (i) $[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z]. These molecules are then involved in a second contact with molecules of type 2 (C7–C12) via N—O⋯Cl interactions [O2⋯Cl4ⁱⁱ = 3.056 (2) Å and N1—O2⋯Cl4ⁱⁱ = 140.1 (1)°; symmetry code: (ii) 1 − x, 1 − y, 1 − z], thus forming 3,4-DCNB ribbons running parallel to the b axis. The aniline solvent molecules, which lie in a perpendicular plane, link these ribbons into an undulating sheet through two N—H⋯O interactions [N3⋯O1ⁱⁱⁱ = 2.52 (2) Å and N3—H1N⋯O1ⁱⁱⁱ = 157 (2)°, and N3⋯O3ⁱ = 2.64 (2) Å and N3—H2N⋯O3ⁱ = 147 (2)°; symmetry code: (iii) 2 − x, 1 − y, 1 − z]. These sheets form an interdigitated ABAB stack parallel to the a axis (Fig. 3).

Figure 1
The asymmetric unit of (I)

, showing the numbering scheme used. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
The two-dimensional network formed by (I)

, showing the intermolecular interactions involved as dashed lines (3,4-DCNB molecule 1: green; 3,4-DCNB molecule 2: blue; aniline: red).

Figure 3
Packing diagram viewed perpendicular to the sheets, illustrating the out-of-plane aniline molecules and the stacking arrangement of the sheets. Intermolecular interactions are shown as dashed lines.

Experimental

A single-crystal sample of the title compound was recrystallized from aniline solution by slow evaporation at ca 293 K.

Crystal data

2C₆H₃Cl₂NO₂·C₆H₇N
M_r = 477.11
Monoclinic, P 2₁ /n
a = 6.9774 (2) Å
b = 10.1668 (3) Å
c = 27.6762 (7) Å
β = 96.495 (2)°
V = 1950.69 (9) Å³
Z = 4
D_x = 1.625 Mg m⁻³
Mo Kα radiation
Cell parameters from 4734 reflections
θ = 1.0–27.9°
μ = 0.64 mm⁻¹
T = 123 (2) K
Triangle, orange
0.45 × 0.30 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
ω and φ scans
Absorption correction: none
22354 measured reflections
4629 independent reflections
3314 reflections with I > 2σ(I)
R_int = 0.058
θ_max = 27.9°
h = −9 → 9
k = −13 → 13
l = −36 → 36

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.081
S = 1.04
4629 reflections
314 parameters
All H-atom parameters refined
w = 1/[σ²(F_o²) + (0.0275P)² + 0.7246P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.32 e Å⁻³

C—H distances are in the range 0.09 (2)–1.00 (2) Å, and N—H distances are 0.86 (2) and 0.87 (2) Å.

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ) and COLLECT; cell refinement: DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000 ) and OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805019999/bt6687sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805019999/bt6687Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

3,4-dichloronitrobenzene–aniline (2/1) top

Crystal data top

2C₆H₃Cl₂NO₂·C₆H₇N	F(000) = 968
M_r = 477.11	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.9774 (2) Å	Cell parameters from 4734 reflections
b = 10.1668 (3) Å	θ = 1.0–27.9°
c = 27.6762 (7) Å	µ = 0.64 mm⁻¹
β = 96.495 (2)°	T = 123 K
V = 1950.69 (9) Å³	Triangle, orange
Z = 4	0.45 × 0.30 × 0.15 mm

Data collection top

Nonius KappaCCD diffractometer	3314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 27.9°, θ_min = 1.5°
ω and φ scans	h = −9→9
22354 measured reflections	k = −13→13
4629 independent reflections	l = −36→36

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0275P)² + 0.7246P] where P = (F_o² + 2F_c²)/3
4629 reflections	(Δ/σ)_max = 0.002
314 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

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
Cl1	0.65101 (8)	0.29879 (5)	0.704181 (17)	0.02699 (13)
Cl2	0.59533 (8)	−0.00859 (5)	0.710847 (18)	0.02975 (14)
O1	0.6570 (2)	0.17232 (14)	0.48418 (5)	0.0305 (4)
O2	0.7091 (3)	0.36004 (14)	0.51992 (5)	0.0384 (4)
N1	0.6761 (2)	0.24168 (17)	0.52060 (6)	0.0232 (4)
C1	0.6599 (3)	0.17966 (19)	0.56799 (7)	0.0180 (4)
C2	0.6634 (3)	0.2596 (2)	0.60845 (7)	0.0190 (4)
C3	0.6455 (3)	0.20088 (19)	0.65295 (7)	0.0179 (4)
C4	0.6246 (3)	0.0651 (2)	0.65591 (7)	0.0200 (4)
C5	0.6249 (3)	−0.0128 (2)	0.61466 (7)	0.0213 (4)
C6	0.6426 (3)	0.0441 (2)	0.57025 (7)	0.0210 (4)
H2	0.679 (3)	0.350 (2)	0.6043 (7)	0.021 (5)*
H5	0.611 (3)	−0.100 (2)	0.6179 (7)	0.026 (6)*
H6	0.640 (3)	−0.0082 (19)	0.5428 (7)	0.023 (6)*
Cl3	0.13987 (8)	0.11529 (5)	0.541764 (17)	0.02701 (13)
Cl4	0.19771 (8)	0.42446 (5)	0.550794 (19)	0.03159 (14)
O3	0.1424 (2)	0.15949 (17)	0.76614 (5)	0.0396 (4)
O4	0.0924 (2)	−0.01482 (16)	0.72154 (6)	0.0385 (4)
N2	0.1219 (2)	0.10362 (19)	0.72661 (6)	0.0276 (4)
C7	0.1347 (3)	0.1830 (2)	0.68264 (7)	0.0199 (4)
C8	0.1309 (3)	0.1183 (2)	0.63845 (7)	0.0197 (4)
C9	0.1471 (3)	0.19368 (19)	0.59743 (7)	0.0190 (4)
C10	0.1676 (3)	0.3298 (2)	0.60112 (7)	0.0217 (4)
C11	0.1690 (3)	0.3914 (2)	0.64595 (8)	0.0246 (5)
C12	0.1527 (3)	0.3178 (2)	0.68721 (7)	0.0250 (5)
H8	0.116 (3)	0.025 (2)	0.6355 (7)	0.024 (6)*
H11	0.181 (3)	0.481 (2)	0.6486 (8)	0.039 (7)*
H12	0.155 (3)	0.359 (2)	0.7179 (8)	0.036 (6)*
N3	1.1864 (3)	0.79026 (19)	0.62461 (8)	0.0298 (4)
C13	1.0052 (3)	0.73193 (19)	0.62348 (7)	0.0217 (4)
C14	0.8979 (3)	0.7006 (2)	0.57924 (7)	0.0263 (5)
C15	0.7159 (3)	0.6460 (2)	0.57829 (8)	0.0304 (5)
C16	0.6376 (3)	0.6211 (2)	0.62136 (8)	0.0297 (5)
C17	0.7429 (3)	0.6525 (2)	0.66525 (8)	0.0269 (5)
C18	0.9240 (3)	0.7080 (2)	0.66656 (7)	0.0241 (5)
H1N	1.246 (3)	0.778 (2)	0.5990 (8)	0.035 (7)*
H2N	1.265 (3)	0.783 (2)	0.6505 (8)	0.035 (7)*
H14	0.959 (3)	0.716 (2)	0.5499 (7)	0.027 (6)*
H15	0.646 (3)	0.625 (2)	0.5480 (8)	0.030 (6)*
H16	0.514 (3)	0.584 (2)	0.6203 (7)	0.021 (5)*
H17	0.689 (3)	0.633 (2)	0.6965 (8)	0.031 (6)*
H18	1.001 (3)	0.727 (2)	0.6966 (8)	0.035 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0332 (3)	0.0285 (3)	0.0199 (3)	−0.0004 (2)	0.0058 (2)	−0.0069 (2)
Cl2	0.0355 (3)	0.0310 (3)	0.0238 (3)	0.0033 (2)	0.0078 (2)	0.0099 (2)
O1	0.0421 (10)	0.0314 (9)	0.0180 (7)	0.0002 (7)	0.0040 (7)	−0.0039 (7)
O2	0.0666 (12)	0.0208 (8)	0.0293 (9)	−0.0109 (8)	0.0119 (8)	0.0038 (7)
N1	0.0258 (10)	0.0241 (10)	0.0201 (9)	−0.0004 (8)	0.0039 (7)	0.0001 (7)
C1	0.0174 (10)	0.0205 (10)	0.0165 (9)	0.0006 (8)	0.0042 (8)	0.0030 (8)
C2	0.0180 (10)	0.0164 (10)	0.0229 (10)	0.0016 (8)	0.0032 (8)	−0.0006 (8)
C3	0.0157 (10)	0.0215 (10)	0.0166 (9)	0.0033 (8)	0.0020 (8)	−0.0041 (8)
C4	0.0162 (10)	0.0243 (10)	0.0198 (10)	0.0020 (8)	0.0028 (8)	0.0053 (8)
C5	0.0213 (11)	0.0156 (10)	0.0272 (11)	−0.0018 (9)	0.0038 (8)	0.0012 (9)
C6	0.0217 (11)	0.0190 (10)	0.0225 (10)	−0.0003 (9)	0.0035 (9)	−0.0032 (9)
Cl3	0.0311 (3)	0.0305 (3)	0.0197 (2)	0.0026 (2)	0.0040 (2)	−0.0058 (2)
Cl4	0.0413 (3)	0.0272 (3)	0.0272 (3)	0.0012 (2)	0.0080 (2)	0.0093 (2)
O3	0.0443 (10)	0.0575 (11)	0.0172 (8)	−0.0067 (8)	0.0046 (7)	−0.0009 (8)
O4	0.0489 (11)	0.0328 (10)	0.0343 (9)	−0.0068 (8)	0.0070 (8)	0.0118 (7)
N2	0.0236 (10)	0.0384 (11)	0.0207 (9)	−0.0025 (9)	0.0030 (7)	0.0063 (8)
C7	0.0178 (10)	0.0239 (11)	0.0183 (10)	−0.0008 (8)	0.0031 (8)	0.0040 (8)
C8	0.0157 (10)	0.0191 (10)	0.0242 (10)	0.0000 (8)	0.0020 (8)	0.0006 (9)
C9	0.0167 (10)	0.0228 (10)	0.0177 (10)	0.0020 (8)	0.0030 (8)	−0.0022 (8)
C10	0.0187 (10)	0.0242 (11)	0.0226 (10)	0.0011 (9)	0.0048 (8)	0.0046 (9)
C11	0.0260 (12)	0.0189 (11)	0.0295 (11)	−0.0007 (9)	0.0050 (9)	−0.0025 (9)
C12	0.0237 (11)	0.0296 (12)	0.0220 (11)	−0.0019 (9)	0.0043 (9)	−0.0055 (9)
N3	0.0291 (11)	0.0332 (11)	0.0284 (11)	−0.0003 (9)	0.0089 (9)	0.0016 (9)
C13	0.0269 (11)	0.0156 (10)	0.0231 (11)	0.0035 (9)	0.0050 (9)	0.0013 (8)
C14	0.0380 (13)	0.0217 (11)	0.0202 (11)	0.0090 (10)	0.0078 (10)	0.0020 (9)
C15	0.0379 (14)	0.0217 (11)	0.0297 (12)	0.0077 (10)	−0.0046 (11)	−0.0065 (10)
C16	0.0288 (13)	0.0178 (11)	0.0431 (14)	0.0009 (10)	0.0061 (11)	−0.0013 (10)
C17	0.0329 (13)	0.0190 (11)	0.0305 (12)	0.0043 (9)	0.0115 (10)	0.0037 (9)
C18	0.0306 (12)	0.0208 (11)	0.0210 (11)	0.0047 (9)	0.0031 (9)	0.0009 (9)

Geometric parameters (Å, º) top

Cl1—C3	1.7293 (19)	C8—C9	1.385 (3)
Cl2—C4	1.7278 (19)	C8—H8	0.96 (2)
O1—N1	1.225 (2)	C9—C10	1.394 (3)
O2—N1	1.226 (2)	C10—C11	1.389 (3)
N1—C1	1.471 (2)	C11—C12	1.380 (3)
C1—C2	1.381 (3)	C11—H11	0.91 (2)
C1—C6	1.385 (3)	C12—H12	0.95 (2)
C2—C3	1.387 (3)	N3—C13	1.393 (3)
C2—H2	0.94 (2)	N3—H1N	0.87 (2)
C3—C4	1.391 (3)	N3—H2N	0.86 (2)
C4—C5	1.390 (3)	C13—C14	1.398 (3)
C5—C6	1.376 (3)	C13—C18	1.398 (3)
C5—H5	0.90 (2)	C14—C15	1.383 (3)
C6—H6	0.93 (2)	C14—H14	0.97 (2)
Cl3—C9	1.7301 (19)	C15—C16	1.389 (3)
Cl4—C10	1.725 (2)	C15—H15	0.95 (2)
O3—N2	1.227 (2)	C16—C17	1.384 (3)
O4—N2	1.227 (2)	C16—H16	0.94 (2)
N2—C7	1.471 (2)	C17—C18	1.381 (3)
C7—C12	1.381 (3)	C17—H17	1.00 (2)
C7—C8	1.386 (3)	C18—H18	0.96 (2)

O1—N1—O2	123.75 (17)	C10—C9—Cl3	121.00 (15)
O1—N1—C1	118.34 (16)	C11—C10—C9	120.24 (18)
O2—N1—C1	117.91 (16)	C11—C10—Cl4	118.70 (16)
C2—C1—C6	122.82 (18)	C9—C10—Cl4	121.04 (15)
C2—C1—N1	118.33 (17)	C12—C11—C10	120.1 (2)
C6—C1—N1	118.85 (17)	C12—C11—H11	119.2 (14)
C1—C2—C3	118.14 (18)	C10—C11—H11	120.7 (14)
C1—C2—H2	118.1 (12)	C11—C12—C7	118.52 (19)
C3—C2—H2	123.8 (12)	C11—C12—H12	120.4 (14)
C2—C3—C4	119.98 (17)	C7—C12—H12	121.0 (14)
C2—C3—Cl1	118.99 (15)	C13—N3—H1N	115.9 (15)
C4—C3—Cl1	121.03 (15)	C13—N3—H2N	118.6 (16)
C5—C4—C3	120.46 (18)	H1N—N3—H2N	111 (2)
C5—C4—Cl2	119.15 (16)	N3—C13—C14	120.76 (19)
C3—C4—Cl2	120.39 (15)	N3—C13—C18	120.62 (19)
C6—C5—C4	120.18 (19)	C14—C13—C18	118.6 (2)
C6—C5—H5	121.7 (13)	C15—C14—C13	120.5 (2)
C4—C5—H5	118.1 (13)	C15—C14—H14	122.4 (12)
C5—C6—C1	118.39 (19)	C13—C14—H14	117.0 (12)
C5—C6—H6	119.7 (12)	C14—C15—C16	120.4 (2)
C1—C6—H6	121.9 (12)	C14—C15—H15	119.2 (13)
O3—N2—O4	123.89 (18)	C16—C15—H15	120.4 (13)
O3—N2—C7	118.15 (18)	C17—C16—C15	119.3 (2)
O4—N2—C7	117.95 (18)	C17—C16—H16	121.0 (12)
C12—C7—C8	122.97 (18)	C15—C16—H16	119.7 (12)
C12—C7—N2	118.83 (18)	C18—C17—C16	120.7 (2)
C8—C7—N2	118.20 (18)	C18—C17—H17	119.4 (12)
C9—C8—C7	117.72 (19)	C16—C17—H17	119.9 (13)
C9—C8—H8	119.8 (12)	C17—C18—C13	120.5 (2)
C7—C8—H8	122.4 (12)	C17—C18—H18	121.8 (13)
C8—C9—C10	120.45 (18)	C13—C18—H18	117.7 (13)
C8—C9—Cl3	118.55 (16)

O1—N1—C1—C2	−174.07 (18)	C12—C7—C8—C9	0.3 (3)
O2—N1—C1—C2	6.3 (3)	N2—C7—C8—C9	−178.68 (17)
O1—N1—C1—C6	6.2 (3)	C7—C8—C9—C10	0.4 (3)
O2—N1—C1—C6	−173.42 (19)	C7—C8—C9—Cl3	−179.25 (15)
C6—C1—C2—C3	−1.2 (3)	C8—C9—C10—C11	−1.1 (3)
N1—C1—C2—C3	179.14 (17)	Cl3—C9—C10—C11	178.60 (15)
C1—C2—C3—C4	0.0 (3)	C8—C9—C10—Cl4	177.36 (15)
C1—C2—C3—Cl1	179.61 (14)	Cl3—C9—C10—Cl4	−3.0 (2)
C2—C3—C4—C5	1.1 (3)	C9—C10—C11—C12	1.0 (3)
Cl1—C3—C4—C5	−178.47 (15)	Cl4—C10—C11—C12	−177.50 (16)
C2—C3—C4—Cl2	−178.18 (14)	C10—C11—C12—C7	−0.2 (3)
Cl1—C3—C4—Cl2	2.2 (2)	C8—C7—C12—C11	−0.4 (3)
C3—C4—C5—C6	−1.1 (3)	N2—C7—C12—C11	178.58 (18)
Cl2—C4—C5—C6	178.16 (16)	N3—C13—C14—C15	−178.26 (19)
C4—C5—C6—C1	0.0 (3)	C18—C13—C14—C15	−0.6 (3)
C2—C1—C6—C5	1.1 (3)	C13—C14—C15—C16	−0.1 (3)
N1—C1—C6—C5	−179.17 (17)	C14—C15—C16—C17	0.4 (3)
O3—N2—C7—C12	−5.4 (3)	C15—C16—C17—C18	0.1 (3)
O4—N2—C7—C12	175.02 (19)	C16—C17—C18—C13	−0.9 (3)
O3—N2—C7—C8	173.64 (18)	N3—C13—C18—C17	178.78 (19)
O4—N2—C7—C8	−5.9 (3)	C14—C13—C18—C17	1.1 (3)

Acknowledgements

The authors acknowledge the Research Councils UK Basic Technology Programme for supporting `Control and Prediction of the Organic Solid State' (www.cposs.org.uk).

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