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Mol­ecules of the title compound, C12H13NO5, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012177/tk2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012177/tk2021Isup2.hkl
Contains datablock I

CCDC reference: 608508

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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
C12H13NO5F(000) = 528
Mr = 251.23Dx = 1.369 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 822 reflections
a = 10.209 (2) Åθ = 2.1–26.4°
b = 15.651 (3) ŵ = 0.11 mm1
c = 7.8920 (17) ÅT = 298 K
β = 104.822 (4)°Polyhedron, yellow
V = 1219.0 (4) Å30.37 × 0.36 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
Rint = 0.068
φ and ω scansθmax = 26.4°, θmin = 2.1°
9643 measured reflectionsh = 1212
2482 independent reflectionsk = 1919
1177 reflections with I > 2σ(I)l = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
O10.52732 (18)1.09009 (11)0.7496 (2)0.0999 (8)
O20.37817 (19)1.00379 (11)0.6098 (2)0.1077 (8)
O30.81043 (14)0.76771 (8)1.11320 (18)0.0657 (5)
O41.00686 (14)0.89882 (10)1.0131 (2)0.0759 (6)
O50.86427 (14)0.93270 (8)1.17710 (17)0.0630 (6)
N10.4828 (2)1.01789 (13)0.7185 (3)0.0692 (8)
C10.5604 (2)0.94721 (14)0.8176 (3)0.0554 (8)
C20.52360 (19)0.86248 (14)0.7831 (2)0.0548 (8)
C30.6084 (2)0.80148 (13)0.8837 (3)0.0566 (8)
C40.72362 (19)0.82280 (13)1.0112 (3)0.0522 (8)
C50.7545 (2)0.90877 (13)1.0417 (3)0.0533 (7)
C60.6750 (2)0.97034 (13)0.9450 (3)0.0566 (8)
C70.2012 (3)0.7791 (2)0.7397 (4)0.1385 (17)
C80.2749 (2)0.83573 (19)0.7175 (4)0.0937 (11)
C90.3999 (2)0.82926 (15)0.6513 (3)0.0713 (9)
C100.8003 (2)0.67947 (13)1.0676 (3)0.0758 (9)
C110.9906 (2)0.92169 (13)1.1494 (3)0.0606 (8)
C121.0950 (2)0.94373 (15)1.3109 (3)0.0879 (10)
H30.586500.744000.864200.0680*
H60.697701.027700.964500.0680*
H7A0.219300.722900.714800.1660*
H7B0.126200.791500.781800.1660*
H80.251300.890500.744800.1130*
H9A0.386600.861700.543500.0860*
H9B0.414500.770000.625200.0860*
H10A0.711000.659201.064500.1140*
H10B0.865900.647601.153200.1140*
H10C0.817400.672100.954400.1140*
H12A1.182300.945301.286200.1320*
H12B1.095400.901501.399200.1320*
H12C1.075200.998701.352100.1320*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1105 (15)0.0648 (11)0.1144 (15)0.0097 (11)0.0105 (12)0.0177 (11)
O20.0919 (13)0.0989 (14)0.1074 (13)0.0147 (11)0.0199 (12)0.0163 (11)
O30.0672 (10)0.0537 (9)0.0678 (9)0.0014 (8)0.0020 (8)0.0059 (7)
O40.0704 (11)0.0847 (11)0.0734 (11)0.0016 (8)0.0199 (9)0.0012 (9)
O50.0600 (10)0.0652 (10)0.0595 (9)0.0076 (7)0.0073 (8)0.0060 (7)
N10.0728 (14)0.0680 (14)0.0681 (13)0.0132 (12)0.0202 (11)0.0112 (12)
C10.0540 (13)0.0582 (14)0.0556 (13)0.0094 (11)0.0170 (11)0.0041 (11)
C20.0485 (12)0.0650 (15)0.0511 (12)0.0018 (11)0.0129 (10)0.0017 (11)
C30.0570 (13)0.0527 (13)0.0606 (13)0.0058 (11)0.0160 (11)0.0022 (11)
C40.0504 (13)0.0528 (13)0.0532 (13)0.0011 (11)0.0128 (11)0.0036 (11)
C50.0518 (13)0.0563 (13)0.0514 (12)0.0040 (11)0.0124 (11)0.0032 (11)
C60.0625 (14)0.0506 (13)0.0581 (13)0.0006 (11)0.0182 (12)0.0026 (11)
C70.098 (3)0.141 (3)0.177 (3)0.003 (2)0.036 (2)0.052 (3)
C80.0551 (16)0.114 (2)0.100 (2)0.0099 (15)0.0023 (15)0.0122 (17)
C90.0594 (15)0.0818 (16)0.0668 (15)0.0004 (12)0.0055 (13)0.0001 (12)
C100.0868 (17)0.0549 (14)0.0837 (16)0.0098 (13)0.0182 (13)0.0068 (12)
C110.0581 (15)0.0504 (13)0.0679 (16)0.0034 (11)0.0064 (13)0.0105 (12)
C120.0690 (16)0.100 (2)0.0812 (17)0.0148 (14)0.0056 (14)0.0010 (14)
Geometric parameters (Å, º) top
O1—N11.219 (3)C8—C91.501 (3)
O2—N11.207 (3)C11—C121.478 (3)
O3—C41.346 (3)C3—H30.9300
O3—C101.424 (2)C6—H60.9300
O4—C111.185 (3)C7—H7A0.9300
O5—C51.388 (3)C7—H7B0.9300
O5—C111.373 (3)C8—H80.9300
N1—C11.465 (3)C9—H9A0.9700
C1—C21.386 (3)C9—H9B0.9700
C1—C61.382 (3)C10—H10A0.9600
C2—C31.393 (3)C10—H10B0.9600
C2—C91.508 (3)C10—H10C0.9600
C3—C41.379 (3)C12—H12A0.9600
C4—C51.389 (3)C12—H12B0.9600
C5—C61.361 (3)C12—H12C0.9600
C7—C81.204 (4)
O2···C83.035 (3)C3···H10A2.7100
O2···C10i3.396 (3)C6···H12Aiii2.9200
O2···C12ii3.364 (3)C8···H12Bii2.8900
O2···C92.753 (3)C10···H12Cx3.1000
O3···C113.001 (3)C10···H32.5600
O3···O52.6613 (19)C12···H7Axi3.0800
O3···O43.109 (2)H3···C102.5600
O4···C43.123 (3)H3···H9B2.2600
O4···C11iii3.091 (3)H3···H10A2.2000
O4···O33.109 (2)H3···H10C2.5400
O4···O4iii3.175 (2)H3···O1viii2.7200
O5···O32.6613 (19)H6···O12.3100
O1···H3i2.7200H6···H8vi2.5600
O1···H9Aiv2.7800H7A···H9B2.3900
O1···H62.3100H7A···C12xii3.0800
O2···H10Ai2.8300H8···O22.5800
O2···H9A2.2900H8···H6vi2.5600
O2···H82.5800H9A···O22.2900
O3···H10Cv2.8400H9A···N12.8600
O5···H10Cv2.8700H9A···O1iv2.7800
N1···C6vi3.445 (3)H9B···H32.2600
N1···H9A2.8600H9B···H7A2.3900
C3···C10vii3.557 (3)H10A···C32.7100
C4···O43.123 (3)H10A···H32.2000
C6···N1vi3.445 (3)H10A···O2viii2.8300
C8···O23.035 (3)H10A···C2v2.9100
C9···O22.753 (3)H10A···C3v3.0300
C10···C3v3.557 (3)H10B···H12Cx2.4100
C10···O2viii3.396 (3)H10C···C32.8900
C11···C11iii3.441 (3)H10C···H32.5400
C11···O33.001 (3)H10C···O3vii2.8400
C11···O4iii3.091 (3)H10C···O5vii2.8700
C12···O2ix3.364 (3)H12A···C6iii2.9200
C2···H10Avii2.9100H12B···C8ix2.8900
C3···H10Avii3.0300H12C···C10xiii3.1000
C3···H10C2.8900H12C···H10Bxiii2.4100
C4—O3—C10118.42 (16)C4—C3—H3119.00
C5—O5—C11116.74 (16)C1—C6—H6120.00
O1—N1—O2121.9 (2)C5—C6—H6120.00
O1—N1—C1118.0 (2)C8—C7—H7A120.00
O2—N1—C1120.05 (19)C8—C7—H7B120.00
N1—C1—C2122.36 (19)H7A—C7—H7B120.00
N1—C1—C6115.61 (19)C7—C8—H8116.00
C2—C1—C6122.0 (2)C9—C8—H8116.00
C1—C2—C3116.50 (18)C2—C9—H9A109.00
C1—C2—C9127.03 (19)C2—C9—H9B109.00
C3—C2—C9116.46 (19)C8—C9—H9A109.00
C2—C3—C4122.67 (19)C8—C9—H9B109.00
O3—C4—C3126.13 (18)H9A—C9—H9B108.00
O3—C4—C5115.56 (19)O3—C10—H10A110.00
C3—C4—C5118.31 (19)O3—C10—H10B109.00
O5—C5—C4119.85 (18)O3—C10—H10C109.00
O5—C5—C6119.27 (18)H10A—C10—H10B109.00
C4—C5—C6120.8 (2)H10A—C10—H10C110.00
C1—C6—C5119.7 (2)H10B—C10—H10C109.00
C7—C8—C9128.3 (3)C11—C12—H12A109.00
C2—C9—C8111.9 (2)C11—C12—H12B109.00
O4—C11—O5122.5 (2)C11—C12—H12C109.00
O4—C11—C12128.0 (2)H12A—C12—H12B109.00
O5—C11—C12109.45 (18)H12A—C12—H12C109.00
C2—C3—H3119.00H12B—C12—H12C109.00
C10—O3—C4—C312.8 (3)N1—C1—C2—C3178.2 (2)
C10—O3—C4—C5168.14 (18)C3—C2—C9—C899.8 (2)
C11—O5—C5—C475.6 (2)C9—C2—C3—C4178.8 (2)
C5—O5—C11—C12175.49 (17)C1—C2—C9—C878.7 (3)
C5—O5—C11—O45.3 (3)C1—C2—C3—C40.2 (3)
C11—O5—C5—C6107.1 (2)C2—C3—C4—C51.1 (3)
O2—N1—C1—C6176.9 (2)C2—C3—C4—O3179.9 (2)
O1—N1—C1—C2175.2 (2)O3—C4—C5—O53.6 (3)
O2—N1—C1—C24.8 (3)C3—C4—C5—O5175.51 (19)
O1—N1—C1—C63.2 (3)C3—C4—C5—C61.7 (3)
C6—C1—C2—C30.1 (3)O3—C4—C5—C6179.1 (2)
N1—C1—C2—C93.3 (3)C4—C5—C6—C11.5 (3)
C6—C1—C2—C9178.4 (2)O5—C5—C6—C1175.74 (19)
C2—C1—C6—C50.6 (3)C7—C8—C9—C2120.2 (3)
N1—C1—C6—C5179.0 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z1; (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, z1/2; (viii) x+1, y1/2, z+3/2; (ix) x+1, y, z+1; (x) x+2, y1/2, z+5/2; (xi) x+1, y+3/2, z+1/2; (xii) x1, y+3/2, z1/2; (xiii) x+2, y+1/2, z+5/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.312.641 (3)100
C8—H8···O20.932.583.035 (3)111
C9—H9A···O20.972.292.753 (3)108
C10—H10A···O2viii0.962.833.396 (3)119
C3—H3···O1viii0.932.723.637 (3)167
Symmetry code: (viii) x+1, y1/2, z+3/2.
 

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