Molecules of the title compound, C
12H
13NO
5, are linked into chains
via weak C—H
π(allyl) interactions and these chains are linked into sheets
via C—H
O contacts; the sheets, in turn, are interconnected
via carbonyl–carbonyl and nitro–π stacking interactions to form a three-dimensional crystal structure.
Supporting information
CCDC reference: 608508
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.113
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C9 .. 7.72 su
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 5.82 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C7 - C8 ... 1.20 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A .. O2 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O1 .. 2.72 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: ...
This is a colaboration between people belonging to different institutions:
- The synthesis and NMR ( 3 people )
- Diffraction ( 2 people )
- Writting of the paper (1 person)
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Bruno et al., 2002).
4-allyl-2-methoxy-5-nitrophenylacetate
top
Crystal data top
C12H13NO5 | F(000) = 528 |
Mr = 251.23 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 822 reflections |
a = 10.209 (2) Å | θ = 2.1–26.4° |
b = 15.651 (3) Å | µ = 0.11 mm−1 |
c = 7.8920 (17) Å | T = 298 K |
β = 104.822 (4)° | Polyhedron, yellow |
V = 1219.0 (4) Å3 | 0.37 × 0.36 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | Rint = 0.068 |
φ and ω scans | θmax = 26.4°, θmin = 2.1° |
9643 measured reflections | h = −12→12 |
2482 independent reflections | k = −19→19 |
1177 reflections with I > 2σ(I) | l = −9→9 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0545P)2] where P = (Fo2 + 2Fc2)/3 |
2482 reflections | (Δ/σ)max = 0.001 |
165 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | Uiso*/Ueq | |
O1 | 0.52732 (18) | 1.09009 (11) | 0.7496 (2) | 0.0999 (8) | |
O2 | 0.37817 (19) | 1.00379 (11) | 0.6098 (2) | 0.1077 (8) | |
O3 | 0.81043 (14) | 0.76771 (8) | 1.11320 (18) | 0.0657 (5) | |
O4 | 1.00686 (14) | 0.89882 (10) | 1.0131 (2) | 0.0759 (6) | |
O5 | 0.86427 (14) | 0.93270 (8) | 1.17710 (17) | 0.0630 (6) | |
N1 | 0.4828 (2) | 1.01789 (13) | 0.7185 (3) | 0.0692 (8) | |
C1 | 0.5604 (2) | 0.94721 (14) | 0.8176 (3) | 0.0554 (8) | |
C2 | 0.52360 (19) | 0.86248 (14) | 0.7831 (2) | 0.0548 (8) | |
C3 | 0.6084 (2) | 0.80148 (13) | 0.8837 (3) | 0.0566 (8) | |
C4 | 0.72362 (19) | 0.82280 (13) | 1.0112 (3) | 0.0522 (8) | |
C5 | 0.7545 (2) | 0.90877 (13) | 1.0417 (3) | 0.0533 (7) | |
C6 | 0.6750 (2) | 0.97034 (13) | 0.9450 (3) | 0.0566 (8) | |
C7 | 0.2012 (3) | 0.7791 (2) | 0.7397 (4) | 0.1385 (17) | |
C8 | 0.2749 (2) | 0.83573 (19) | 0.7175 (4) | 0.0937 (11) | |
C9 | 0.3999 (2) | 0.82926 (15) | 0.6513 (3) | 0.0713 (9) | |
C10 | 0.8003 (2) | 0.67947 (13) | 1.0676 (3) | 0.0758 (9) | |
C11 | 0.9906 (2) | 0.92169 (13) | 1.1494 (3) | 0.0606 (8) | |
C12 | 1.0950 (2) | 0.94373 (15) | 1.3109 (3) | 0.0879 (10) | |
H3 | 0.58650 | 0.74400 | 0.86420 | 0.0680* | |
H6 | 0.69770 | 1.02770 | 0.96450 | 0.0680* | |
H7A | 0.21930 | 0.72290 | 0.71480 | 0.1660* | |
H7B | 0.12620 | 0.79150 | 0.78180 | 0.1660* | |
H8 | 0.25130 | 0.89050 | 0.74480 | 0.1130* | |
H9A | 0.38660 | 0.86170 | 0.54350 | 0.0860* | |
H9B | 0.41450 | 0.77000 | 0.62520 | 0.0860* | |
H10A | 0.71100 | 0.65920 | 1.06450 | 0.1140* | |
H10B | 0.86590 | 0.64760 | 1.15320 | 0.1140* | |
H10C | 0.81740 | 0.67210 | 0.95440 | 0.1140* | |
H12A | 1.18230 | 0.94530 | 1.28620 | 0.1320* | |
H12B | 1.09540 | 0.90150 | 1.39920 | 0.1320* | |
H12C | 1.07520 | 0.99870 | 1.35210 | 0.1320* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1105 (15) | 0.0648 (11) | 0.1144 (15) | 0.0097 (11) | 0.0105 (12) | 0.0177 (11) |
O2 | 0.0919 (13) | 0.0989 (14) | 0.1074 (13) | 0.0147 (11) | −0.0199 (12) | 0.0163 (11) |
O3 | 0.0672 (10) | 0.0537 (9) | 0.0678 (9) | 0.0014 (8) | 0.0020 (8) | 0.0059 (7) |
O4 | 0.0704 (11) | 0.0847 (11) | 0.0734 (11) | 0.0016 (8) | 0.0199 (9) | −0.0012 (9) |
O5 | 0.0600 (10) | 0.0652 (10) | 0.0595 (9) | −0.0076 (7) | 0.0073 (8) | −0.0060 (7) |
N1 | 0.0728 (14) | 0.0680 (14) | 0.0681 (13) | 0.0132 (12) | 0.0202 (11) | 0.0112 (12) |
C1 | 0.0540 (13) | 0.0582 (14) | 0.0556 (13) | 0.0094 (11) | 0.0170 (11) | 0.0041 (11) |
C2 | 0.0485 (12) | 0.0650 (15) | 0.0511 (12) | 0.0018 (11) | 0.0129 (10) | 0.0017 (11) |
C3 | 0.0570 (13) | 0.0527 (13) | 0.0606 (13) | −0.0058 (11) | 0.0160 (11) | −0.0022 (11) |
C4 | 0.0504 (13) | 0.0528 (13) | 0.0532 (13) | 0.0011 (11) | 0.0128 (11) | 0.0036 (11) |
C5 | 0.0518 (13) | 0.0563 (13) | 0.0514 (12) | −0.0040 (11) | 0.0124 (11) | −0.0032 (11) |
C6 | 0.0625 (14) | 0.0506 (13) | 0.0581 (13) | 0.0006 (11) | 0.0182 (12) | −0.0026 (11) |
C7 | 0.098 (3) | 0.141 (3) | 0.177 (3) | 0.003 (2) | 0.036 (2) | 0.052 (3) |
C8 | 0.0551 (16) | 0.114 (2) | 0.100 (2) | −0.0099 (15) | −0.0023 (15) | 0.0122 (17) |
C9 | 0.0594 (15) | 0.0818 (16) | 0.0668 (15) | −0.0004 (12) | 0.0055 (13) | 0.0001 (12) |
C10 | 0.0868 (17) | 0.0549 (14) | 0.0837 (16) | 0.0098 (13) | 0.0182 (13) | 0.0068 (12) |
C11 | 0.0581 (15) | 0.0504 (13) | 0.0679 (16) | −0.0034 (11) | 0.0064 (13) | 0.0105 (12) |
C12 | 0.0690 (16) | 0.100 (2) | 0.0812 (17) | −0.0148 (14) | −0.0056 (14) | −0.0010 (14) |
Geometric parameters (Å, º) top
O1—N1 | 1.219 (3) | C8—C9 | 1.501 (3) |
O2—N1 | 1.207 (3) | C11—C12 | 1.478 (3) |
O3—C4 | 1.346 (3) | C3—H3 | 0.9300 |
O3—C10 | 1.424 (2) | C6—H6 | 0.9300 |
O4—C11 | 1.185 (3) | C7—H7A | 0.9300 |
O5—C5 | 1.388 (3) | C7—H7B | 0.9300 |
O5—C11 | 1.373 (3) | C8—H8 | 0.9300 |
N1—C1 | 1.465 (3) | C9—H9A | 0.9700 |
C1—C2 | 1.386 (3) | C9—H9B | 0.9700 |
C1—C6 | 1.382 (3) | C10—H10A | 0.9600 |
C2—C3 | 1.393 (3) | C10—H10B | 0.9600 |
C2—C9 | 1.508 (3) | C10—H10C | 0.9600 |
C3—C4 | 1.379 (3) | C12—H12A | 0.9600 |
C4—C5 | 1.389 (3) | C12—H12B | 0.9600 |
C5—C6 | 1.361 (3) | C12—H12C | 0.9600 |
C7—C8 | 1.204 (4) | | |
| | | |
O2···C8 | 3.035 (3) | C3···H10A | 2.7100 |
O2···C10i | 3.396 (3) | C6···H12Aiii | 2.9200 |
O2···C12ii | 3.364 (3) | C8···H12Bii | 2.8900 |
O2···C9 | 2.753 (3) | C10···H12Cx | 3.1000 |
O3···C11 | 3.001 (3) | C10···H3 | 2.5600 |
O3···O5 | 2.6613 (19) | C12···H7Axi | 3.0800 |
O3···O4 | 3.109 (2) | H3···C10 | 2.5600 |
O4···C4 | 3.123 (3) | H3···H9B | 2.2600 |
O4···C11iii | 3.091 (3) | H3···H10A | 2.2000 |
O4···O3 | 3.109 (2) | H3···H10C | 2.5400 |
O4···O4iii | 3.175 (2) | H3···O1viii | 2.7200 |
O5···O3 | 2.6613 (19) | H6···O1 | 2.3100 |
O1···H3i | 2.7200 | H6···H8vi | 2.5600 |
O1···H9Aiv | 2.7800 | H7A···H9B | 2.3900 |
O1···H6 | 2.3100 | H7A···C12xii | 3.0800 |
O2···H10Ai | 2.8300 | H8···O2 | 2.5800 |
O2···H9A | 2.2900 | H8···H6vi | 2.5600 |
O2···H8 | 2.5800 | H9A···O2 | 2.2900 |
O3···H10Cv | 2.8400 | H9A···N1 | 2.8600 |
O5···H10Cv | 2.8700 | H9A···O1iv | 2.7800 |
N1···C6vi | 3.445 (3) | H9B···H3 | 2.2600 |
N1···H9A | 2.8600 | H9B···H7A | 2.3900 |
C3···C10vii | 3.557 (3) | H10A···C3 | 2.7100 |
C4···O4 | 3.123 (3) | H10A···H3 | 2.2000 |
C6···N1vi | 3.445 (3) | H10A···O2viii | 2.8300 |
C8···O2 | 3.035 (3) | H10A···C2v | 2.9100 |
C9···O2 | 2.753 (3) | H10A···C3v | 3.0300 |
C10···C3v | 3.557 (3) | H10B···H12Cx | 2.4100 |
C10···O2viii | 3.396 (3) | H10C···C3 | 2.8900 |
C11···C11iii | 3.441 (3) | H10C···H3 | 2.5400 |
C11···O3 | 3.001 (3) | H10C···O3vii | 2.8400 |
C11···O4iii | 3.091 (3) | H10C···O5vii | 2.8700 |
C12···O2ix | 3.364 (3) | H12A···C6iii | 2.9200 |
C2···H10Avii | 2.9100 | H12B···C8ix | 2.8900 |
C3···H10Avii | 3.0300 | H12C···C10xiii | 3.1000 |
C3···H10C | 2.8900 | H12C···H10Bxiii | 2.4100 |
| | | |
C4—O3—C10 | 118.42 (16) | C4—C3—H3 | 119.00 |
C5—O5—C11 | 116.74 (16) | C1—C6—H6 | 120.00 |
O1—N1—O2 | 121.9 (2) | C5—C6—H6 | 120.00 |
O1—N1—C1 | 118.0 (2) | C8—C7—H7A | 120.00 |
O2—N1—C1 | 120.05 (19) | C8—C7—H7B | 120.00 |
N1—C1—C2 | 122.36 (19) | H7A—C7—H7B | 120.00 |
N1—C1—C6 | 115.61 (19) | C7—C8—H8 | 116.00 |
C2—C1—C6 | 122.0 (2) | C9—C8—H8 | 116.00 |
C1—C2—C3 | 116.50 (18) | C2—C9—H9A | 109.00 |
C1—C2—C9 | 127.03 (19) | C2—C9—H9B | 109.00 |
C3—C2—C9 | 116.46 (19) | C8—C9—H9A | 109.00 |
C2—C3—C4 | 122.67 (19) | C8—C9—H9B | 109.00 |
O3—C4—C3 | 126.13 (18) | H9A—C9—H9B | 108.00 |
O3—C4—C5 | 115.56 (19) | O3—C10—H10A | 110.00 |
C3—C4—C5 | 118.31 (19) | O3—C10—H10B | 109.00 |
O5—C5—C4 | 119.85 (18) | O3—C10—H10C | 109.00 |
O5—C5—C6 | 119.27 (18) | H10A—C10—H10B | 109.00 |
C4—C5—C6 | 120.8 (2) | H10A—C10—H10C | 110.00 |
C1—C6—C5 | 119.7 (2) | H10B—C10—H10C | 109.00 |
C7—C8—C9 | 128.3 (3) | C11—C12—H12A | 109.00 |
C2—C9—C8 | 111.9 (2) | C11—C12—H12B | 109.00 |
O4—C11—O5 | 122.5 (2) | C11—C12—H12C | 109.00 |
O4—C11—C12 | 128.0 (2) | H12A—C12—H12B | 109.00 |
O5—C11—C12 | 109.45 (18) | H12A—C12—H12C | 109.00 |
C2—C3—H3 | 119.00 | H12B—C12—H12C | 109.00 |
| | | |
C10—O3—C4—C3 | 12.8 (3) | N1—C1—C2—C3 | 178.2 (2) |
C10—O3—C4—C5 | −168.14 (18) | C3—C2—C9—C8 | 99.8 (2) |
C11—O5—C5—C4 | 75.6 (2) | C9—C2—C3—C4 | −178.8 (2) |
C5—O5—C11—C12 | −175.49 (17) | C1—C2—C9—C8 | −78.7 (3) |
C5—O5—C11—O4 | 5.3 (3) | C1—C2—C3—C4 | −0.2 (3) |
C11—O5—C5—C6 | −107.1 (2) | C2—C3—C4—C5 | 1.1 (3) |
O2—N1—C1—C6 | −176.9 (2) | C2—C3—C4—O3 | −179.9 (2) |
O1—N1—C1—C2 | −175.2 (2) | O3—C4—C5—O5 | −3.6 (3) |
O2—N1—C1—C2 | 4.8 (3) | C3—C4—C5—O5 | 175.51 (19) |
O1—N1—C1—C6 | 3.2 (3) | C3—C4—C5—C6 | −1.7 (3) |
C6—C1—C2—C3 | −0.1 (3) | O3—C4—C5—C6 | 179.1 (2) |
N1—C1—C2—C9 | −3.3 (3) | C4—C5—C6—C1 | 1.5 (3) |
C6—C1—C2—C9 | 178.4 (2) | O5—C5—C6—C1 | −175.74 (19) |
C2—C1—C6—C5 | −0.6 (3) | C7—C8—C9—C2 | −120.2 (3) |
N1—C1—C6—C5 | −179.0 (2) | | |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z−1; (iii) −x+2, −y+2, −z+2; (iv) −x+1, −y+2, −z+1; (v) x, −y+3/2, z+1/2; (vi) −x+1, −y+2, −z+2; (vii) x, −y+3/2, z−1/2; (viii) −x+1, y−1/2, −z+3/2; (ix) x+1, y, z+1; (x) −x+2, y−1/2, −z+5/2; (xi) x+1, −y+3/2, z+1/2; (xii) x−1, −y+3/2, z−1/2; (xiii) −x+2, y+1/2, −z+5/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.31 | 2.641 (3) | 100 |
C8—H8···O2 | 0.93 | 2.58 | 3.035 (3) | 111 |
C9—H9A···O2 | 0.97 | 2.29 | 2.753 (3) | 108 |
C10—H10A···O2viii | 0.96 | 2.83 | 3.396 (3) | 119 |
C3—H3···O1viii | 0.93 | 2.72 | 3.637 (3) | 167 |
Symmetry code: (viii) −x+1, y−1/2, −z+3/2. |