organic compounds
4-Nitroaniline–2,4,6-trimethoxybenzaldehyde (1/1)
aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title 6H6N2O2.C10H12O4, the two components are held together by an N—H⋯Oaldehyde hydrogen bond. Adjacent co-crystals are linked by weaker N—H⋯Onitro hydrogen bonds, forming a linear chain. The two aromatic rings of the components are aligned at 75.2 (1)°. The crystal studied was a non-merohedral twin with a 24% minor component.
CRelated literature
For some examples of co-crystals of 4-nitroaniline, see: Bertolasi et al. (2001); Dederer & Gieren (1979); Huang et al. (1996); Koshima et al. (1996); Rashid & Deschamps (2006); Singh et al. (2003); Smith et al. (1997); Weber (1981); Zaitu et al. (1995). For the treatment of non-merohedral twins, see: Spek (2009).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536810023664/si2271sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810023664/si2271Isup2.hkl
2,4, 6-Trimethoxybenzaldehyde (0.50 g, 3.3 mmol) and 4-nitroaniline (0.57 g, 3.3 mmol) were heated in methanol (15 ml) for 5 h. Yellow crystals separated from the cool solution after a day.
Carbon- and nitrogen-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, N–H 0.86 Å; U(H) 1.2 to 1.5Ueq(C,N)] and were included in the
in the riding model approximation.The crystal studied is a non-merohedral twin; the
(1 0 0.121, 0 - 1 0, 0 0 - 1) as given by PLATON (Spek, 2009) was used to de-twin the diffraction data.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the C6H6N2O2–C10H12O4 co-crystal at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
C6H6N2O2·C10H12O4 | F(000) = 704 |
Mr = 334.32 | Dx = 1.435 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1019 reflections |
a = 7.4409 (11) Å | θ = 2.7–24.4° |
b = 30.022 (5) Å | µ = 0.11 mm−1 |
c = 6.9400 (11) Å | T = 100 K |
β = 93.237 (3)° | Prism, yellow |
V = 1547.9 (4) Å3 | 0.15 × 0.10 × 0.05 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 1834 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 25.0°, θmin = 1.4° |
ω scans | h = −8→8 |
8127 measured reflections | k = −32→35 |
2722 independent reflections | l = −8→8 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.141P] where P = (Fo2 + 2Fc2)/3 |
2722 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C6H6N2O2·C10H12O4 | V = 1547.9 (4) Å3 |
Mr = 334.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4409 (11) Å | µ = 0.11 mm−1 |
b = 30.022 (5) Å | T = 100 K |
c = 6.9400 (11) Å | 0.15 × 0.10 × 0.05 mm |
β = 93.237 (3)° |
Bruker SMART APEX diffractometer | 1834 reflections with I > 2σ(I) |
8127 measured reflections | Rint = 0.059 |
2722 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.22 e Å−3 |
2722 reflections | Δρmin = −0.41 e Å−3 |
221 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7019 (2) | 0.57392 (6) | 0.7861 (3) | 0.0238 (5) | |
O2 | 0.7670 (2) | 0.61120 (6) | 0.4418 (2) | 0.0182 (4) | |
O3 | 1.3371 (2) | 0.57367 (6) | 0.1850 (2) | 0.0203 (4) | |
O4 | 1.1646 (2) | 0.51253 (6) | 0.7725 (2) | 0.0176 (4) | |
O5 | 0.0363 (2) | 0.80574 (6) | 0.5273 (3) | 0.0266 (5) | |
O6 | −0.0908 (2) | 0.74324 (7) | 0.4450 (3) | 0.0291 (5) | |
N1 | 0.6593 (3) | 0.67379 (7) | 0.7727 (3) | 0.0233 (5) | |
H11 | 0.7505 | 0.6884 | 0.8209 | 0.028* | |
H12 | 0.6631 | 0.6452 | 0.7670 | 0.028* | |
N2 | 0.0398 (3) | 0.76456 (7) | 0.5159 (3) | 0.0193 (5) | |
C1 | 0.8433 (3) | 0.55435 (8) | 0.7589 (4) | 0.0177 (6) | |
H1 | 0.8764 | 0.5314 | 0.8482 | 0.021* | |
C2 | 0.9658 (3) | 0.56212 (8) | 0.6066 (3) | 0.0152 (6) | |
C3 | 0.9285 (3) | 0.59010 (8) | 0.4462 (4) | 0.0154 (6) | |
C4 | 1.0482 (3) | 0.59515 (8) | 0.3011 (4) | 0.0155 (6) | |
H4 | 1.0203 | 0.6140 | 0.1936 | 0.019* | |
C5 | 1.2098 (3) | 0.57189 (8) | 0.3175 (4) | 0.0157 (6) | |
C6 | 1.2542 (3) | 0.54410 (8) | 0.4744 (4) | 0.0170 (6) | |
H6 | 1.3662 | 0.5289 | 0.4834 | 0.020* | |
C7 | 1.1335 (3) | 0.53914 (8) | 0.6155 (3) | 0.0144 (6) | |
C8 | 0.7184 (3) | 0.63908 (9) | 0.2781 (4) | 0.0216 (6) | |
H8A | 0.5983 | 0.6516 | 0.2923 | 0.032* | |
H8B | 0.7179 | 0.6213 | 0.1597 | 0.032* | |
H8C | 0.8061 | 0.6633 | 0.2709 | 0.032* | |
C9 | 1.3034 (3) | 0.60080 (8) | 0.0177 (4) | 0.0198 (6) | |
H9A | 1.4039 | 0.5980 | −0.0669 | 0.030* | |
H9B | 1.2913 | 0.6320 | 0.0570 | 0.030* | |
H9C | 1.1920 | 0.5910 | −0.0516 | 0.030* | |
C10 | 1.3340 (3) | 0.48903 (9) | 0.7879 (4) | 0.0193 (6) | |
H10A | 1.3403 | 0.4709 | 0.9054 | 0.029* | |
H10B | 1.4332 | 0.5106 | 0.7934 | 0.029* | |
H10C | 1.3436 | 0.4697 | 0.6751 | 0.029* | |
C11 | 0.5099 (3) | 0.69579 (9) | 0.7057 (3) | 0.0168 (6) | |
C12 | 0.3577 (3) | 0.67245 (9) | 0.6292 (4) | 0.0189 (6) | |
H12A | 0.3622 | 0.6409 | 0.6183 | 0.023* | |
C13 | 0.2034 (3) | 0.69466 (9) | 0.5705 (4) | 0.0186 (6) | |
H13 | 0.1006 | 0.6786 | 0.5216 | 0.022* | |
C14 | 0.1986 (3) | 0.74094 (8) | 0.5832 (4) | 0.0165 (6) | |
C15 | 0.3483 (3) | 0.76498 (8) | 0.6542 (3) | 0.0162 (6) | |
H15 | 0.3440 | 0.7966 | 0.6610 | 0.019* | |
C16 | 0.5015 (3) | 0.74254 (9) | 0.7139 (4) | 0.0176 (6) | |
H16 | 0.6040 | 0.7588 | 0.7617 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0193 (10) | 0.0228 (11) | 0.0302 (11) | 0.0076 (8) | 0.0082 (8) | 0.0052 (9) |
O2 | 0.0152 (9) | 0.0201 (10) | 0.0195 (10) | 0.0065 (8) | 0.0028 (7) | 0.0045 (8) |
O3 | 0.0188 (10) | 0.0228 (11) | 0.0200 (10) | 0.0060 (8) | 0.0070 (8) | 0.0085 (8) |
O4 | 0.0163 (9) | 0.0172 (10) | 0.0195 (10) | 0.0054 (7) | 0.0023 (7) | 0.0049 (8) |
O5 | 0.0257 (11) | 0.0204 (12) | 0.0337 (12) | 0.0076 (9) | 0.0015 (8) | 0.0010 (9) |
O6 | 0.0173 (10) | 0.0360 (13) | 0.0332 (12) | −0.0005 (9) | −0.0068 (9) | −0.0050 (10) |
N1 | 0.0213 (12) | 0.0170 (13) | 0.0311 (13) | 0.0035 (10) | −0.0030 (10) | −0.0009 (11) |
N2 | 0.0183 (12) | 0.0219 (14) | 0.0178 (12) | 0.0011 (10) | 0.0028 (9) | −0.0001 (10) |
C1 | 0.0207 (14) | 0.0123 (14) | 0.0201 (14) | 0.0010 (12) | 0.0005 (11) | 0.0014 (11) |
C2 | 0.0160 (13) | 0.0131 (14) | 0.0165 (13) | −0.0013 (10) | 0.0012 (10) | −0.0016 (11) |
C3 | 0.0133 (13) | 0.0136 (14) | 0.0189 (13) | 0.0016 (11) | −0.0017 (10) | −0.0027 (11) |
C4 | 0.0157 (13) | 0.0139 (14) | 0.0171 (13) | −0.0008 (10) | 0.0015 (10) | −0.0010 (11) |
C5 | 0.0154 (13) | 0.0147 (14) | 0.0174 (13) | −0.0017 (11) | 0.0039 (10) | −0.0015 (11) |
C6 | 0.0136 (13) | 0.0142 (14) | 0.0230 (14) | 0.0022 (11) | −0.0003 (11) | 0.0002 (11) |
C7 | 0.0190 (14) | 0.0098 (14) | 0.0141 (13) | −0.0002 (10) | −0.0012 (10) | −0.0018 (11) |
C8 | 0.0207 (14) | 0.0211 (16) | 0.0227 (14) | 0.0046 (12) | −0.0017 (11) | 0.0062 (12) |
C9 | 0.0239 (15) | 0.0173 (15) | 0.0185 (14) | 0.0015 (11) | 0.0035 (11) | 0.0044 (12) |
C10 | 0.0148 (13) | 0.0199 (15) | 0.0230 (14) | 0.0057 (11) | 0.0004 (11) | 0.0045 (12) |
C11 | 0.0205 (14) | 0.0186 (15) | 0.0118 (13) | 0.0037 (11) | 0.0052 (11) | −0.0005 (11) |
C12 | 0.0246 (14) | 0.0121 (14) | 0.0200 (14) | −0.0020 (12) | 0.0025 (11) | 0.0003 (11) |
C13 | 0.0175 (14) | 0.0218 (16) | 0.0166 (14) | −0.0044 (12) | 0.0029 (11) | −0.0013 (12) |
C14 | 0.0154 (13) | 0.0175 (15) | 0.0168 (13) | 0.0009 (11) | 0.0011 (10) | 0.0009 (11) |
C15 | 0.0212 (14) | 0.0122 (14) | 0.0158 (13) | −0.0003 (11) | 0.0056 (11) | −0.0014 (11) |
C16 | 0.0165 (13) | 0.0210 (16) | 0.0152 (13) | 0.0000 (11) | 0.0011 (11) | −0.0023 (11) |
O1—C1 | 1.229 (3) | C6—C7 | 1.374 (3) |
O2—C3 | 1.357 (3) | C6—H6 | 0.9500 |
O2—C8 | 1.441 (3) | C8—H8A | 0.9800 |
O3—C5 | 1.358 (3) | C8—H8B | 0.9800 |
O3—C9 | 1.428 (3) | C8—H8C | 0.9800 |
O4—C7 | 1.360 (3) | C9—H9A | 0.9800 |
O4—C10 | 1.444 (3) | C9—H9B | 0.9800 |
O5—N2 | 1.239 (3) | C9—H9C | 0.9800 |
O6—N2 | 1.242 (3) | C10—H10A | 0.9800 |
N1—C11 | 1.352 (3) | C10—H10B | 0.9800 |
N1—H11 | 0.8600 | C10—H10C | 0.9800 |
N1—H12 | 0.8600 | C11—C16 | 1.406 (4) |
N2—C14 | 1.434 (3) | C11—C12 | 1.410 (3) |
C1—C2 | 1.454 (3) | C12—C13 | 1.370 (3) |
C1—H1 | 0.9500 | C12—H12A | 0.9500 |
C2—C3 | 1.409 (3) | C13—C14 | 1.393 (3) |
C2—C7 | 1.424 (3) | C13—H13 | 0.9500 |
C3—C4 | 1.390 (3) | C14—C15 | 1.394 (3) |
C4—C5 | 1.389 (3) | C15—C16 | 1.368 (3) |
C4—H4 | 0.9500 | C15—H15 | 0.9500 |
C5—C6 | 1.397 (3) | C16—H16 | 0.9500 |
C3—O2—C8 | 118.10 (19) | O2—C8—H8C | 109.5 |
C5—O3—C9 | 118.39 (19) | H8A—C8—H8C | 109.5 |
C7—O4—C10 | 117.03 (19) | H8B—C8—H8C | 109.5 |
C11—N1—H11 | 120.0 | O3—C9—H9A | 109.5 |
C11—N1—H12 | 120.0 | O3—C9—H9B | 109.5 |
H11—N1—H12 | 120.0 | H9A—C9—H9B | 109.5 |
O5—N2—O6 | 121.4 (2) | O3—C9—H9C | 109.5 |
O5—N2—C14 | 119.5 (2) | H9A—C9—H9C | 109.5 |
O6—N2—C14 | 119.1 (2) | H9B—C9—H9C | 109.5 |
O1—C1—C2 | 127.8 (2) | O4—C10—H10A | 109.5 |
O1—C1—H1 | 116.1 | O4—C10—H10B | 109.5 |
C2—C1—H1 | 116.1 | H10A—C10—H10B | 109.5 |
C3—C2—C7 | 117.2 (2) | O4—C10—H10C | 109.5 |
C3—C2—C1 | 124.5 (2) | H10A—C10—H10C | 109.5 |
C7—C2—C1 | 118.3 (2) | H10B—C10—H10C | 109.5 |
O2—C3—C4 | 122.4 (2) | N1—C11—C16 | 120.7 (2) |
O2—C3—C2 | 115.5 (2) | N1—C11—C12 | 120.9 (2) |
C4—C3—C2 | 122.1 (2) | C16—C11—C12 | 118.3 (2) |
C3—C4—C5 | 118.2 (2) | C13—C12—C11 | 120.8 (2) |
C3—C4—H4 | 120.9 | C13—C12—H12A | 119.6 |
C5—C4—H4 | 120.9 | C11—C12—H12A | 119.6 |
O3—C5—C4 | 123.9 (2) | C12—C13—C14 | 119.4 (2) |
O3—C5—C6 | 114.1 (2) | C12—C13—H13 | 120.3 |
C4—C5—C6 | 122.0 (2) | C14—C13—H13 | 120.3 |
C7—C6—C5 | 119.0 (2) | C15—C14—C13 | 121.1 (2) |
C7—C6—H6 | 120.5 | C15—C14—N2 | 119.1 (2) |
C5—C6—H6 | 120.5 | C13—C14—N2 | 119.7 (2) |
O4—C7—C6 | 123.1 (2) | C16—C15—C14 | 119.2 (2) |
O4—C7—C2 | 115.4 (2) | C16—C15—H15 | 120.4 |
C6—C7—C2 | 121.5 (2) | C14—C15—H15 | 120.4 |
O2—C8—H8A | 109.5 | C15—C16—C11 | 121.2 (2) |
O2—C8—H8B | 109.5 | C15—C16—H16 | 119.4 |
H8A—C8—H8B | 109.5 | C11—C16—H16 | 119.4 |
O1—C1—C2—C3 | −9.3 (4) | C5—C6—C7—C2 | −0.9 (4) |
O1—C1—C2—C7 | 172.5 (2) | C3—C2—C7—O4 | 179.9 (2) |
C8—O2—C3—C4 | 1.2 (3) | C1—C2—C7—O4 | −1.8 (3) |
C8—O2—C3—C2 | −177.9 (2) | C3—C2—C7—C6 | 0.2 (3) |
C7—C2—C3—O2 | 179.5 (2) | C1—C2—C7—C6 | 178.6 (2) |
C1—C2—C3—O2 | 1.3 (4) | N1—C11—C12—C13 | 176.7 (2) |
C7—C2—C3—C4 | 0.5 (3) | C16—C11—C12—C13 | −2.2 (4) |
C1—C2—C3—C4 | −177.7 (2) | C11—C12—C13—C14 | 1.3 (4) |
O2—C3—C4—C5 | −179.5 (2) | C12—C13—C14—C15 | 0.2 (4) |
C2—C3—C4—C5 | −0.5 (4) | C12—C13—C14—N2 | 177.8 (2) |
C9—O3—C5—C4 | −0.4 (3) | O5—N2—C14—C15 | −2.2 (3) |
C9—O3—C5—C6 | 179.3 (2) | O6—N2—C14—C15 | 176.9 (2) |
C3—C4—C5—O3 | 179.4 (2) | O5—N2—C14—C13 | −179.9 (2) |
C3—C4—C5—C6 | −0.2 (4) | O6—N2—C14—C13 | −0.8 (3) |
O3—C5—C6—C7 | −178.8 (2) | C13—C14—C15—C16 | −0.6 (4) |
C4—C5—C6—C7 | 0.9 (4) | N2—C14—C15—C16 | −178.3 (2) |
C10—O4—C7—C6 | 0.3 (3) | C14—C15—C16—C11 | −0.3 (4) |
C10—O4—C7—C2 | −179.4 (2) | N1—C11—C16—C15 | −177.2 (2) |
C5—C6—C7—O4 | 179.5 (2) | C12—C11—C16—C15 | 1.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O1 | 0.86 | 2.16 | 3.016 (3) | 172 |
N1—H11···O5i | 0.86 | 2.50 | 3.288 (3) | 152 |
N1—H11···O6i | 0.86 | 2.50 | 3.293 (3) | 154 |
Symmetry code: (i) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H6N2O2·C10H12O4 |
Mr | 334.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.4409 (11), 30.022 (5), 6.9400 (11) |
β (°) | 93.237 (3) |
V (Å3) | 1547.9 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.15 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8127, 2722, 1834 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.124, 1.01 |
No. of reflections | 2722 |
No. of parameters | 221 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.41 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O1 | 0.86 | 2.16 | 3.016 (3) | 172 |
N1—H11···O5i | 0.86 | 2.50 | 3.288 (3) | 152 |
N1—H11···O6i | 0.86 | 2.50 | 3.293 (3) | 154 |
Symmetry code: (i) x+1, −y+3/2, z+1/2. |
Acknowledgements
We thank King Abdul Aziz University and the University of Malaya for supporting this study.
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Aromatic aldehydes readily condense with aromatic amines to yield Schiff bases. However, 2,4,6-trimethoxylbenzaldehyde and 4-nitroaniline reactants did not condense but instead co-crystallized in the attempted synthesis. The condensation probably did not proceed owing to the decreased basicity of the amino group, which is situated opposite the electron-withdrawing nitro group in the aromatic ring. The co-crystal (Scheme I, Fig. 1) has the components linked by an H–N···O hydrogen bond; the two aromatic rings aligned at 75.2 (1) °. Adjacent co-crystals are linked by weaker N–H···Onitro hydrogen bonds to form a linear chain.
4-Nitroaniline forms a number of co-crystals with other neutral compounds; for their description, see: Bertolasi et al. (2001); Dederer & Gieren (1979); Huang et al. (1996); Koshima et al. (1996); Rashid & Deschamps (2006); Singh et al. (2003); Smith et al. (1997); Weber (1981); Zaitu et al. (1995).