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In the title mol­ecule, C10H8N204, the phthalimide unit is essentially planar. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link mol­ecules into one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051312/lh2258sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051312/lh2258Isup2.hkl
Contains datablock I

CCDC reference: 633914

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.136
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT145_ALERT_4_C su on beta Small or Missing (x 10000) ..... 0 Deg. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N1 .. 5.02 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-ethyl-5-nitroisoindoline-1,3-dione top
Crystal data top
C10H8N2O4F(000) = 456
Mr = 220.18Dx = 1.453 Mg m3
Orthorhombic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1449 reflections
a = 4.9438 (16) Åθ = 2.3–23.9°
b = 20.655 (6) ŵ = 0.12 mm1
c = 9.858 (3) ÅT = 294 K
V = 1006.6 (6) Å3Plate, yellow
Z = 40.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2058 independent reflections
Radiation source: fine-focus sealed tube1216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 63
Tmin = 0.973, Tmax = 0.980k = 2525
5567 measured reflectionsl = 1112
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.069P)2 + 0.0778P]
where P = (Fo2 + 2Fc2)/3
2058 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O10.1628 (4)0.50681 (8)0.3659 (2)0.0816 (6)
O20.1694 (4)0.45405 (8)0.2747 (2)0.0734 (6)
O30.6900 (3)0.19123 (8)0.53988 (18)0.0681 (5)
O40.0137 (3)0.19014 (8)0.23681 (17)0.0642 (5)
N10.0465 (4)0.45631 (10)0.3363 (2)0.0544 (5)
N20.3491 (4)0.17427 (8)0.38199 (17)0.0450 (5)
C10.5107 (4)0.21190 (11)0.4675 (2)0.0448 (5)
C20.4159 (4)0.28065 (10)0.4503 (2)0.0405 (5)
C30.5048 (4)0.33738 (10)0.5102 (2)0.0474 (6)
H30.64380.33720.57370.057*
C40.3781 (5)0.39502 (11)0.4717 (2)0.0480 (6)
H40.43250.43420.50950.058*
C50.1708 (4)0.39365 (10)0.3768 (2)0.0422 (5)
C60.0758 (4)0.33702 (10)0.3162 (2)0.0432 (5)
H60.06460.33720.25340.052*
C70.2042 (4)0.28037 (10)0.3556 (2)0.0391 (5)
C80.1562 (4)0.21166 (10)0.3136 (2)0.0430 (5)
C90.3705 (5)0.10351 (10)0.3706 (2)0.0527 (6)
H9A0.55920.09150.36100.063*
H9B0.27550.08920.28990.063*
C100.2522 (6)0.06981 (12)0.4940 (3)0.0704 (8)
H10A0.36190.07900.57200.106*
H10B0.24840.02390.47860.106*
H10C0.07150.08520.50940.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0971 (15)0.0395 (10)0.1082 (16)0.0062 (10)0.0127 (13)0.0000 (10)
O20.0672 (12)0.0621 (12)0.0911 (14)0.0114 (9)0.0176 (11)0.0136 (9)
O30.0657 (11)0.0613 (11)0.0772 (12)0.0115 (9)0.0356 (10)0.0004 (9)
O40.0673 (11)0.0556 (10)0.0698 (11)0.0052 (9)0.0339 (9)0.0093 (8)
N10.0600 (14)0.0459 (12)0.0573 (13)0.0058 (10)0.0028 (11)0.0072 (10)
N20.0459 (10)0.0403 (10)0.0489 (11)0.0013 (8)0.0097 (9)0.0019 (8)
C10.0409 (12)0.0481 (13)0.0455 (13)0.0011 (10)0.0084 (10)0.0002 (10)
C20.0352 (11)0.0443 (12)0.0421 (12)0.0019 (9)0.0053 (10)0.0025 (9)
C30.0429 (12)0.0521 (14)0.0471 (14)0.0062 (11)0.0117 (11)0.0001 (10)
C40.0489 (13)0.0438 (13)0.0513 (14)0.0070 (11)0.0009 (11)0.0031 (10)
C50.0428 (13)0.0391 (12)0.0447 (13)0.0001 (10)0.0032 (10)0.0048 (9)
C60.0386 (12)0.0473 (13)0.0437 (13)0.0027 (10)0.0072 (10)0.0054 (10)
C70.0353 (11)0.0417 (12)0.0402 (12)0.0027 (9)0.0041 (9)0.0020 (9)
C80.0419 (12)0.0460 (13)0.0412 (12)0.0001 (10)0.0062 (10)0.0021 (10)
C90.0597 (15)0.0411 (13)0.0572 (15)0.0043 (11)0.0067 (12)0.0047 (11)
C100.0781 (19)0.0505 (16)0.083 (2)0.0027 (13)0.0058 (16)0.0064 (13)
Geometric parameters (Å, º) top
O1—N11.226 (2)C4—C51.388 (3)
O2—N11.229 (2)C4—H40.9300
O3—C11.215 (2)C5—C61.395 (3)
O4—C81.215 (2)C6—C71.387 (3)
N1—C51.487 (3)C6—H60.9300
N2—C11.398 (2)C7—C81.497 (3)
N2—C81.400 (3)C9—C101.519 (3)
N2—C91.469 (3)C9—H9A0.9700
C1—C21.505 (3)C9—H9B0.9700
C2—C31.383 (3)C10—H10A0.9600
C2—C71.403 (3)C10—H10B0.9600
C3—C41.398 (3)C10—H10C0.9600
C3—H30.9300
O1—N1—O2123.9 (2)C7—C6—C5115.68 (19)
O1—N1—C5118.9 (2)C7—C6—H6122.2
O2—N1—C5117.3 (2)C5—C6—H6122.2
C1—N2—C8111.90 (18)C6—C7—C2121.64 (19)
C1—N2—C9123.93 (17)C6—C7—C8130.53 (18)
C8—N2—C9124.11 (17)C2—C7—C8107.83 (18)
O3—C1—N2125.1 (2)O4—C8—N2124.7 (2)
O3—C1—C2128.7 (2)O4—C8—C7128.95 (19)
N2—C1—C2106.18 (16)N2—C8—C7106.37 (17)
C3—C2—C7121.6 (2)N2—C9—C10111.50 (19)
C3—C2—C1130.70 (19)N2—C9—H9A109.3
C7—C2—C1107.67 (18)C10—C9—H9A109.3
C2—C3—C4117.6 (2)N2—C9—H9B109.3
C2—C3—H3121.2C10—C9—H9B109.3
C4—C3—H3121.2H9A—C9—H9B108.0
C5—C4—C3119.8 (2)C9—C10—H10A109.5
C5—C4—H4120.1C9—C10—H10B109.5
C3—C4—H4120.1H10A—C10—H10B109.5
C4—C5—C6123.7 (2)C9—C10—H10C109.5
C4—C5—N1117.92 (19)H10A—C10—H10C109.5
C6—C5—N1118.40 (19)H10B—C10—H10C109.5
C8—N2—C1—O3178.7 (2)N1—C5—C6—C7178.46 (18)
C9—N2—C1—O31.6 (3)C5—C6—C7—C20.1 (3)
C8—N2—C1—C21.2 (2)C5—C6—C7—C8179.5 (2)
C9—N2—C1—C2178.37 (19)C3—C2—C7—C60.7 (3)
O3—C1—C2—C30.1 (4)C1—C2—C7—C6179.02 (19)
N2—C1—C2—C3179.9 (2)C3—C2—C7—C8178.9 (2)
O3—C1—C2—C7179.9 (2)C1—C2—C7—C81.3 (2)
N2—C1—C2—C70.1 (2)C1—N2—C8—O4177.6 (2)
C7—C2—C3—C40.8 (3)C9—N2—C8—O40.4 (3)
C1—C2—C3—C4178.9 (2)C1—N2—C8—C72.1 (2)
C2—C3—C4—C50.2 (3)C9—N2—C8—C7179.18 (19)
C3—C4—C5—C60.5 (3)C6—C7—C8—O42.1 (4)
C3—C4—C5—N1178.50 (19)C2—C7—C8—O4177.5 (2)
O1—N1—C5—C414.3 (3)C6—C7—C8—N2178.3 (2)
O2—N1—C5—C4165.6 (2)C2—C7—C8—N22.1 (2)
O1—N1—C5—C6164.8 (2)C1—N2—C9—C1074.0 (3)
O2—N1—C5—C615.3 (3)C8—N2—C9—C10102.8 (2)
C4—C5—C6—C70.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.932.503.376 (2)157
C3—H3···O4ii0.932.403.314 (2)167
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2.
 

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