organic compounds
Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate
aCollege of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Science, and College of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wanghaibo@njut.edu.cn
The 12H14ClNO6, contains two crystallographically independent molecules, in which the benzene rings are oriented at a dihedral angle of 9.12 (3)°. In the weak intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.
of the title compound, CRelated literature
For general background, see: Knesl et al. (2006). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536809009076/hk2642sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809009076/hk2642Isup2.hkl
For the preparation of the title compound, a solution of methyl 4-(3-chloro- propoxy)-3-methoxybenzoate (19 mmol) in acetic acid (20 ml) was added dropwise to nitric acid (98%, 4.5 ml) at 273-278 K. The mixture was stirred for 1 h at room temperature, and then for 2 h at 323 K. After the reaction was completed, the reaction mixture was poured into ice/water (130 ml), and then extracted with trichloromethane (20 ml). The combined organic phases were collected, washed with saturated sodium bicarbonate (20 ml), brine (20 ml), dried (Na2SO4) and decolorized (charcoal). Trichloromethane was then removed under reduced pressure to give a yellow oil, which was crystallized from ethyl acetate/petroleum ether to afford the product as light yellow crystals (m.p. 337 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C12H14ClNO6 | F(000) = 1264 |
Mr = 303.69 | Dx = 1.441 Mg m−3 |
Monoclinic, P21/c | Melting point: 337 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.150 (5) Å | Cell parameters from 25 reflections |
b = 15.013 (3) Å | θ = 10–13° |
c = 8.0700 (16) Å | µ = 0.30 mm−1 |
β = 93.42 (3)° | T = 294 K |
V = 2799.7 (10) Å3 | Needle, yellow |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 2874 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 25.3°, θmin = 1.6° |
ω/2θ scans | h = 0→27 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→18 |
Tmin = 0.916, Tmax = 0.943 | l = −9→9 |
5208 measured reflections | 3 standard reflections every 120 min |
5096 independent reflections | intensity decay: 1% |
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)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0567P)2 + 1.915P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5096 reflections | Δρmax = 0.40 e Å−3 |
362 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0049 (6) |
C12H14ClNO6 | V = 2799.7 (10) Å3 |
Mr = 303.69 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 23.150 (5) Å | µ = 0.30 mm−1 |
b = 15.013 (3) Å | T = 294 K |
c = 8.0700 (16) Å | 0.30 × 0.20 × 0.20 mm |
β = 93.42 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2874 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.038 |
Tmin = 0.916, Tmax = 0.943 | 3 standard reflections every 120 min |
5208 measured reflections | intensity decay: 1% |
5096 independent reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.40 e Å−3 |
5096 reflections | Δρmin = −0.30 e Å−3 |
362 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.26534 (6) | 0.48992 (8) | 0.29390 (17) | 0.0758 (4) | |
Cl2 | 0.30461 (6) | 0.79461 (8) | 0.6560 (2) | 0.0888 (5) | |
O1 | −0.10537 (13) | 0.2705 (2) | 0.1972 (5) | 0.0846 (11) | |
O2 | −0.05735 (14) | 0.1596 (2) | 0.3282 (4) | 0.0714 (9) | |
O3 | −0.06317 (19) | 0.3963 (3) | 0.4296 (5) | 0.1081 (15) | |
O4 | −0.05061 (16) | 0.5014 (2) | 0.2559 (6) | 0.0970 (13) | |
O5 | 0.13459 (12) | 0.23218 (18) | 0.0445 (4) | 0.0559 (8) | |
O6 | 0.14060 (12) | 0.40304 (18) | 0.0445 (4) | 0.0593 (8) | |
O7 | 0.40610 (12) | 0.06586 (17) | 0.5910 (4) | 0.0558 (8) | |
O8 | 0.48185 (14) | 0.1024 (2) | 0.7607 (4) | 0.0740 (10) | |
O9 | 0.53876 (12) | 0.3392 (2) | 0.6019 (4) | 0.0637 (9) | |
O10 | 0.51561 (13) | 0.2122 (2) | 0.4944 (4) | 0.0694 (9) | |
O11 | 0.28231 (11) | 0.33078 (17) | 0.7787 (4) | 0.0528 (7) | |
O12 | 0.34201 (12) | 0.46634 (17) | 0.7009 (4) | 0.0538 (8) | |
N1 | −0.04080 (17) | 0.4270 (3) | 0.3109 (6) | 0.0687 (11) | |
N2 | 0.50447 (14) | 0.2793 (2) | 0.5715 (4) | 0.0466 (8) | |
C1 | −0.1592 (2) | 0.2271 (5) | 0.2275 (9) | 0.124 (3) | |
H1A | −0.1907 | 0.2607 | 0.1761 | 0.185* | |
H1B | −0.1635 | 0.2237 | 0.3449 | 0.185* | |
H1C | −0.1593 | 0.1681 | 0.1816 | 0.185* | |
C2 | −0.05727 (18) | 0.2299 (3) | 0.2610 (6) | 0.0554 (11) | |
C3 | −0.00469 (17) | 0.2813 (3) | 0.2209 (5) | 0.0477 (10) | |
C4 | 0.00118 (18) | 0.3722 (3) | 0.2282 (5) | 0.0495 (10) | |
C5 | 0.04788 (18) | 0.4163 (3) | 0.1691 (5) | 0.0542 (11) | |
H5A | 0.0498 | 0.4781 | 0.1724 | 0.065* | |
C6 | 0.09190 (17) | 0.3675 (3) | 0.1046 (5) | 0.0474 (10) | |
C7 | 0.08873 (17) | 0.2742 (3) | 0.1040 (5) | 0.0463 (10) | |
C8 | 0.04040 (17) | 0.2321 (3) | 0.1598 (5) | 0.0476 (10) | |
H8A | 0.0380 | 0.1702 | 0.1564 | 0.057* | |
C9 | 0.1376 (2) | 0.1372 (3) | 0.0606 (6) | 0.0626 (12) | |
H9A | 0.1721 | 0.1159 | 0.0133 | 0.094* | |
H9B | 0.1043 | 0.1109 | 0.0033 | 0.094* | |
H9C | 0.1384 | 0.1213 | 0.1759 | 0.094* | |
C10 | 0.1491 (2) | 0.4975 (3) | 0.0631 (7) | 0.0645 (13) | |
H10A | 0.1494 | 0.5140 | 0.1794 | 0.077* | |
H10B | 0.1182 | 0.5297 | 0.0031 | 0.077* | |
C11 | 0.2060 (2) | 0.5190 (3) | −0.0057 (6) | 0.0638 (13) | |
H11A | 0.2128 | 0.5825 | 0.0057 | 0.077* | |
H11B | 0.2037 | 0.5053 | −0.1234 | 0.077* | |
C12 | 0.25688 (19) | 0.4705 (3) | 0.0750 (6) | 0.0612 (12) | |
H12A | 0.2918 | 0.4893 | 0.0241 | 0.073* | |
H12B | 0.2521 | 0.4071 | 0.0553 | 0.073* | |
C13 | 0.4229 (2) | −0.0264 (3) | 0.6021 (7) | 0.0748 (15) | |
H13A | 0.3962 | −0.0617 | 0.5344 | 0.112* | |
H13B | 0.4226 | −0.0458 | 0.7154 | 0.112* | |
H13C | 0.4611 | −0.0332 | 0.5638 | 0.112* | |
C14 | 0.43940 (17) | 0.1222 (3) | 0.6788 (5) | 0.0433 (10) | |
C15 | 0.41457 (15) | 0.2145 (2) | 0.6687 (4) | 0.0367 (9) | |
C16 | 0.35887 (16) | 0.2280 (2) | 0.7183 (5) | 0.0409 (9) | |
H16A | 0.3365 | 0.1790 | 0.7442 | 0.049* | |
C17 | 0.33587 (16) | 0.3122 (2) | 0.7300 (5) | 0.0397 (9) | |
C18 | 0.36847 (16) | 0.3871 (2) | 0.6871 (5) | 0.0415 (9) | |
C19 | 0.42370 (16) | 0.3744 (2) | 0.6376 (5) | 0.0418 (9) | |
H19A | 0.4460 | 0.4231 | 0.6098 | 0.050* | |
C20 | 0.44601 (15) | 0.2890 (2) | 0.6293 (4) | 0.0378 (9) | |
C21 | 0.24745 (17) | 0.2586 (3) | 0.8302 (5) | 0.0521 (11) | |
H21A | 0.2108 | 0.2811 | 0.8613 | 0.078* | |
H21B | 0.2667 | 0.2292 | 0.9235 | 0.078* | |
H21C | 0.2414 | 0.2171 | 0.7404 | 0.078* | |
C22 | 0.3705 (2) | 0.5435 (3) | 0.6460 (6) | 0.0567 (11) | |
H22A | 0.3781 | 0.5384 | 0.5295 | 0.068* | |
H22B | 0.4070 | 0.5523 | 0.7096 | 0.068* | |
C23 | 0.3290 (2) | 0.6207 (3) | 0.6738 (7) | 0.0680 (14) | |
H23A | 0.2931 | 0.6108 | 0.6080 | 0.082* | |
H23B | 0.3201 | 0.6222 | 0.7897 | 0.082* | |
C24 | 0.3531 (2) | 0.7046 (3) | 0.6292 (8) | 0.0895 (18) | |
H24A | 0.3629 | 0.7024 | 0.5141 | 0.107* | |
H24B | 0.3885 | 0.7149 | 0.6969 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0858 (9) | 0.0698 (8) | 0.0709 (8) | −0.0107 (7) | −0.0018 (7) | −0.0109 (7) |
Cl2 | 0.0811 (9) | 0.0518 (7) | 0.1376 (13) | 0.0225 (6) | 0.0417 (9) | 0.0179 (8) |
O1 | 0.049 (2) | 0.095 (3) | 0.111 (3) | −0.0011 (18) | 0.0157 (19) | 0.046 (2) |
O2 | 0.071 (2) | 0.066 (2) | 0.079 (2) | −0.0029 (17) | 0.0184 (18) | 0.0170 (19) |
O3 | 0.124 (3) | 0.119 (3) | 0.087 (3) | 0.048 (3) | 0.053 (3) | 0.017 (3) |
O4 | 0.088 (3) | 0.059 (2) | 0.148 (4) | 0.018 (2) | 0.037 (2) | 0.006 (2) |
O5 | 0.0529 (18) | 0.0488 (17) | 0.068 (2) | −0.0020 (14) | 0.0179 (15) | −0.0026 (15) |
O6 | 0.0515 (18) | 0.0475 (17) | 0.080 (2) | −0.0126 (14) | 0.0128 (16) | −0.0039 (15) |
O7 | 0.0585 (18) | 0.0382 (15) | 0.069 (2) | 0.0053 (14) | −0.0072 (15) | −0.0044 (15) |
O8 | 0.064 (2) | 0.064 (2) | 0.089 (2) | 0.0219 (17) | −0.0301 (19) | −0.0083 (18) |
O9 | 0.0436 (17) | 0.071 (2) | 0.078 (2) | −0.0114 (16) | 0.0142 (15) | −0.0192 (17) |
O10 | 0.062 (2) | 0.060 (2) | 0.089 (2) | 0.0059 (16) | 0.0290 (18) | −0.0250 (18) |
O11 | 0.0425 (16) | 0.0458 (16) | 0.072 (2) | 0.0063 (13) | 0.0190 (14) | −0.0015 (15) |
O12 | 0.0547 (18) | 0.0370 (15) | 0.072 (2) | 0.0082 (13) | 0.0231 (15) | 0.0010 (14) |
N1 | 0.062 (3) | 0.070 (3) | 0.075 (3) | 0.008 (2) | 0.011 (2) | 0.000 (2) |
N2 | 0.041 (2) | 0.051 (2) | 0.049 (2) | 0.0044 (17) | 0.0083 (16) | −0.0039 (18) |
C1 | 0.048 (3) | 0.155 (6) | 0.171 (7) | −0.014 (4) | 0.023 (4) | 0.067 (5) |
C2 | 0.048 (3) | 0.068 (3) | 0.052 (3) | 0.001 (2) | 0.014 (2) | 0.001 (2) |
C3 | 0.044 (2) | 0.056 (3) | 0.043 (2) | 0.004 (2) | 0.0049 (19) | 0.001 (2) |
C4 | 0.046 (2) | 0.055 (3) | 0.048 (3) | 0.005 (2) | 0.005 (2) | −0.008 (2) |
C5 | 0.052 (3) | 0.045 (2) | 0.065 (3) | −0.001 (2) | −0.003 (2) | −0.003 (2) |
C6 | 0.043 (2) | 0.051 (3) | 0.048 (3) | −0.005 (2) | 0.000 (2) | −0.001 (2) |
C7 | 0.048 (3) | 0.046 (2) | 0.044 (2) | −0.002 (2) | 0.000 (2) | −0.006 (2) |
C8 | 0.050 (3) | 0.044 (2) | 0.049 (3) | −0.005 (2) | 0.006 (2) | 0.001 (2) |
C9 | 0.063 (3) | 0.049 (3) | 0.078 (3) | −0.001 (2) | 0.017 (2) | −0.006 (2) |
C10 | 0.060 (3) | 0.042 (2) | 0.092 (4) | −0.007 (2) | 0.002 (3) | 0.003 (2) |
C11 | 0.073 (3) | 0.047 (3) | 0.071 (3) | −0.014 (2) | 0.004 (3) | 0.005 (2) |
C12 | 0.058 (3) | 0.059 (3) | 0.067 (3) | −0.009 (2) | 0.013 (2) | −0.007 (2) |
C13 | 0.082 (4) | 0.036 (2) | 0.106 (4) | 0.005 (2) | 0.001 (3) | 0.000 (3) |
C14 | 0.044 (2) | 0.046 (2) | 0.041 (2) | 0.004 (2) | 0.0054 (19) | −0.0019 (19) |
C15 | 0.038 (2) | 0.039 (2) | 0.033 (2) | 0.0017 (17) | 0.0013 (17) | −0.0016 (17) |
C16 | 0.041 (2) | 0.036 (2) | 0.046 (2) | −0.0013 (17) | 0.0048 (18) | 0.0002 (18) |
C17 | 0.036 (2) | 0.044 (2) | 0.040 (2) | 0.0053 (18) | 0.0084 (17) | −0.0025 (18) |
C18 | 0.046 (2) | 0.039 (2) | 0.041 (2) | 0.0089 (19) | 0.0060 (18) | −0.0043 (18) |
C19 | 0.049 (2) | 0.039 (2) | 0.039 (2) | −0.0025 (18) | 0.0081 (18) | −0.0030 (18) |
C20 | 0.035 (2) | 0.044 (2) | 0.035 (2) | 0.0052 (17) | 0.0059 (16) | −0.0034 (17) |
C21 | 0.046 (2) | 0.058 (3) | 0.053 (3) | −0.004 (2) | 0.013 (2) | −0.004 (2) |
C22 | 0.068 (3) | 0.040 (2) | 0.063 (3) | 0.007 (2) | 0.016 (2) | 0.001 (2) |
C23 | 0.074 (3) | 0.046 (3) | 0.087 (4) | 0.006 (2) | 0.030 (3) | −0.001 (3) |
C24 | 0.080 (4) | 0.061 (3) | 0.131 (5) | 0.013 (3) | 0.036 (4) | −0.002 (3) |
Cl1—C12 | 1.789 (5) | C9—H9A | 0.9600 |
Cl2—C24 | 1.778 (5) | C9—H9B | 0.9600 |
O1—C2 | 1.345 (5) | C9—H9C | 0.9600 |
O1—C1 | 1.439 (5) | C10—C11 | 1.496 (6) |
O2—C2 | 1.187 (5) | C10—H10A | 0.9700 |
O3—N1 | 1.208 (5) | C10—H10B | 0.9700 |
O4—N1 | 1.218 (5) | C11—C12 | 1.500 (6) |
O5—C7 | 1.348 (5) | C11—H11A | 0.9700 |
O5—C9 | 1.433 (5) | C11—H11B | 0.9700 |
O6—C6 | 1.363 (4) | C12—H12A | 0.9700 |
O6—C10 | 1.438 (5) | C12—H12B | 0.9700 |
O7—C14 | 1.322 (5) | C13—H13A | 0.9600 |
O7—C13 | 1.440 (5) | C13—H13B | 0.9600 |
O8—C14 | 1.189 (4) | C13—H13C | 0.9600 |
O9—N2 | 1.215 (4) | C14—C15 | 1.501 (5) |
O10—N2 | 1.220 (4) | C15—C20 | 1.382 (5) |
O11—C17 | 1.352 (4) | C15—C16 | 1.388 (5) |
O11—C21 | 1.427 (4) | C16—C17 | 1.377 (5) |
O12—C18 | 1.346 (4) | C16—H16A | 0.9300 |
O12—C22 | 1.417 (5) | C17—C18 | 1.409 (5) |
N1—C4 | 1.464 (5) | C18—C19 | 1.375 (5) |
N2—C20 | 1.465 (5) | C19—C20 | 1.385 (5) |
C1—H1A | 0.9600 | C19—H19A | 0.9300 |
C1—H1B | 0.9600 | C21—H21A | 0.9600 |
C1—H1C | 0.9600 | C21—H21B | 0.9600 |
C2—C3 | 1.493 (6) | C21—H21C | 0.9600 |
C3—C4 | 1.372 (5) | C22—C23 | 1.530 (5) |
C3—C8 | 1.393 (5) | C22—H22A | 0.9700 |
C4—C5 | 1.377 (6) | C22—H22B | 0.9700 |
C5—C6 | 1.381 (5) | C23—C24 | 1.432 (6) |
C5—H5A | 0.9300 | C23—H23A | 0.9700 |
C6—C7 | 1.402 (5) | C23—H23B | 0.9700 |
C7—C8 | 1.384 (5) | C24—H24A | 0.9700 |
C8—H8A | 0.9300 | C24—H24B | 0.9700 |
C2—O1—C1 | 115.8 (4) | C11—C12—Cl1 | 112.7 (3) |
C7—O5—C9 | 118.0 (3) | C11—C12—H12A | 109.0 |
C6—O6—C10 | 117.4 (3) | Cl1—C12—H12A | 109.0 |
C14—O7—C13 | 115.8 (3) | C11—C12—H12B | 109.0 |
C17—O11—C21 | 118.2 (3) | Cl1—C12—H12B | 109.0 |
C18—O12—C22 | 118.3 (3) | H12A—C12—H12B | 107.8 |
O3—N1—O4 | 124.0 (4) | O7—C13—H13A | 109.5 |
O3—N1—C4 | 118.3 (4) | O7—C13—H13B | 109.5 |
O4—N1—C4 | 117.6 (4) | H13A—C13—H13B | 109.5 |
O9—N2—O10 | 124.0 (3) | O7—C13—H13C | 109.5 |
O9—N2—C20 | 117.9 (3) | H13A—C13—H13C | 109.5 |
O10—N2—C20 | 118.2 (3) | H13B—C13—H13C | 109.5 |
O1—C1—H1A | 109.5 | O8—C14—O7 | 125.0 (4) |
O1—C1—H1B | 109.5 | O8—C14—C15 | 124.2 (4) |
H1A—C1—H1B | 109.5 | O7—C14—C15 | 110.7 (3) |
O1—C1—H1C | 109.5 | C20—C15—C16 | 117.3 (3) |
H1A—C1—H1C | 109.5 | C20—C15—C14 | 123.7 (3) |
H1B—C1—H1C | 109.5 | C16—C15—C14 | 118.6 (3) |
O2—C2—O1 | 123.7 (4) | C17—C16—C15 | 121.6 (3) |
O2—C2—C3 | 125.6 (4) | C17—C16—H16A | 119.2 |
O1—C2—C3 | 110.5 (4) | C15—C16—H16A | 119.2 |
C4—C3—C8 | 118.0 (4) | O11—C17—C16 | 125.1 (3) |
C4—C3—C2 | 125.8 (4) | O11—C17—C18 | 114.9 (3) |
C8—C3—C2 | 116.1 (4) | C16—C17—C18 | 120.0 (3) |
C3—C4—C5 | 122.7 (4) | O12—C18—C19 | 125.6 (4) |
C3—C4—N1 | 120.8 (4) | O12—C18—C17 | 115.6 (3) |
C5—C4—N1 | 116.4 (4) | C19—C18—C17 | 118.8 (3) |
C4—C5—C6 | 119.2 (4) | C18—C19—C20 | 119.8 (3) |
C4—C5—H5A | 120.4 | C18—C19—H19A | 120.1 |
C6—C5—H5A | 120.4 | C20—C19—H19A | 120.1 |
O6—C6—C5 | 124.9 (4) | C15—C20—C19 | 122.3 (3) |
O6—C6—C7 | 115.7 (4) | C15—C20—N2 | 120.1 (3) |
C5—C6—C7 | 119.4 (4) | C19—C20—N2 | 117.5 (3) |
O5—C7—C8 | 124.8 (4) | O11—C21—H21A | 109.5 |
O5—C7—C6 | 115.3 (3) | O11—C21—H21B | 109.5 |
C8—C7—C6 | 119.9 (4) | H21A—C21—H21B | 109.5 |
C7—C8—C3 | 120.6 (4) | O11—C21—H21C | 109.5 |
C7—C8—H8A | 119.7 | H21A—C21—H21C | 109.5 |
C3—C8—H8A | 119.7 | H21B—C21—H21C | 109.5 |
O5—C9—H9A | 109.5 | O12—C22—C23 | 105.3 (3) |
O5—C9—H9B | 109.5 | O12—C22—H22A | 110.7 |
H9A—C9—H9B | 109.5 | C23—C22—H22A | 110.7 |
O5—C9—H9C | 109.5 | O12—C22—H22B | 110.7 |
H9A—C9—H9C | 109.5 | C23—C22—H22B | 110.7 |
H9B—C9—H9C | 109.5 | H22A—C22—H22B | 108.8 |
O6—C10—C11 | 107.0 (4) | C24—C23—C22 | 111.8 (4) |
O6—C10—H10A | 110.3 | C24—C23—H23A | 109.2 |
C11—C10—H10A | 110.3 | C22—C23—H23A | 109.2 |
O6—C10—H10B | 110.3 | C24—C23—H23B | 109.2 |
C11—C10—H10B | 110.3 | C22—C23—H23B | 109.2 |
H10A—C10—H10B | 108.6 | H23A—C23—H23B | 107.9 |
C10—C11—C12 | 114.8 (4) | C23—C24—Cl2 | 112.4 (4) |
C10—C11—H11A | 108.6 | C23—C24—H24A | 109.1 |
C12—C11—H11A | 108.6 | Cl2—C24—H24A | 109.1 |
C10—C11—H11B | 108.6 | C23—C24—H24B | 109.1 |
C12—C11—H11B | 108.6 | Cl2—C24—H24B | 109.1 |
H11A—C11—H11B | 107.5 | H24A—C24—H24B | 107.9 |
C1—O1—C2—O2 | 5.3 (7) | C13—O7—C14—O8 | 1.8 (6) |
C1—O1—C2—C3 | 179.9 (5) | C13—O7—C14—C15 | −175.1 (3) |
O2—C2—C3—C4 | −143.1 (5) | O8—C14—C15—C20 | 53.4 (6) |
O1—C2—C3—C4 | 42.5 (6) | O7—C14—C15—C20 | −129.7 (4) |
O2—C2—C3—C8 | 41.7 (6) | O8—C14—C15—C16 | −119.6 (5) |
O1—C2—C3—C8 | −132.8 (4) | O7—C14—C15—C16 | 57.4 (5) |
C8—C3—C4—C5 | 3.9 (6) | C20—C15—C16—C17 | −0.8 (5) |
C2—C3—C4—C5 | −171.3 (4) | C14—C15—C16—C17 | 172.6 (4) |
C8—C3—C4—N1 | −171.9 (4) | C21—O11—C17—C16 | 3.3 (6) |
C2—C3—C4—N1 | 12.9 (7) | C21—O11—C17—C18 | −177.7 (3) |
O3—N1—C4—C3 | 33.0 (7) | C15—C16—C17—O11 | −179.4 (3) |
O4—N1—C4—C3 | −147.6 (4) | C15—C16—C17—C18 | 1.6 (6) |
O3—N1—C4—C5 | −143.1 (5) | C22—O12—C18—C19 | 6.2 (6) |
O4—N1—C4—C5 | 36.3 (6) | C22—O12—C18—C17 | −174.6 (4) |
C3—C4—C5—C6 | −2.3 (7) | O11—C17—C18—O12 | 0.2 (5) |
N1—C4—C5—C6 | 173.7 (4) | C16—C17—C18—O12 | 179.3 (3) |
C10—O6—C6—C5 | 5.8 (6) | O11—C17—C18—C19 | 179.4 (3) |
C10—O6—C6—C7 | −172.0 (4) | C16—C17—C18—C19 | −1.5 (6) |
C4—C5—C6—O6 | −179.1 (4) | O12—C18—C19—C20 | 179.7 (4) |
C4—C5—C6—C7 | −1.4 (6) | C17—C18—C19—C20 | 0.6 (6) |
C9—O5—C7—C8 | −9.0 (6) | C16—C15—C20—C19 | −0.2 (5) |
C9—O5—C7—C6 | 172.0 (4) | C14—C15—C20—C19 | −173.2 (4) |
O6—C6—C7—O5 | 0.3 (5) | C16—C15—C20—N2 | −178.3 (3) |
C5—C6—C7—O5 | −177.6 (4) | C14—C15—C20—N2 | 8.7 (6) |
O6—C6—C7—C8 | −178.8 (3) | C18—C19—C20—C15 | 0.3 (6) |
C5—C6—C7—C8 | 3.3 (6) | C18—C19—C20—N2 | 178.4 (3) |
O5—C7—C8—C3 | 179.3 (4) | O9—N2—C20—C15 | −150.4 (4) |
C6—C7—C8—C3 | −1.7 (6) | O10—N2—C20—C15 | 30.4 (5) |
C4—C3—C8—C7 | −1.8 (6) | O9—N2—C20—C19 | 31.4 (5) |
C2—C3—C8—C7 | 173.8 (4) | O10—N2—C20—C19 | −147.8 (4) |
C6—O6—C10—C11 | 177.8 (4) | C18—O12—C22—C23 | 178.5 (4) |
O6—C10—C11—C12 | −58.2 (5) | O12—C22—C23—C24 | 177.8 (5) |
C10—C11—C12—Cl1 | −57.8 (5) | C22—C23—C24—Cl2 | 178.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O4i | 0.97 | 2.58 | 3.336 (7) | 135 |
C13—H13B···O9ii | 0.96 | 2.41 | 3.211 (6) | 141 |
C21—H21A···O5iii | 0.96 | 2.48 | 3.243 (5) | 136 |
C24—H24A···O9iv | 0.97 | 2.59 | 3.276 (6) | 128 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C12H14ClNO6 |
Mr | 303.69 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 23.150 (5), 15.013 (3), 8.0700 (16) |
β (°) | 93.42 (3) |
V (Å3) | 2799.7 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.916, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5208, 5096, 2874 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.162, 1.03 |
No. of reflections | 5096 |
No. of parameters | 362 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.30 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O4i | 0.97 | 2.58 | 3.336 (7) | 135 |
C13—H13B···O9ii | 0.96 | 2.41 | 3.211 (6) | 141 |
C21—H21A···O5iii | 0.96 | 2.48 | 3.243 (5) | 136 |
C24—H24A···O9iv | 0.97 | 2.59 | 3.276 (6) | 128 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1. |
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of our ongoing studies on quinazoline derivatives (Knesl et al., 2006), we report herein the crystal structure of the title compound.
The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8) and A' (C15-C20) are, of course, planar and they are oriented at a dihedral angle of A/A' = 9.12 (3)°.
In the crystal structure, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.