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The title compound, C14H9NO2, was synthesized by the electrophilic aromatic substitution reaction between anthracene and nitric acid. The crystal structure is a low-temperature (100 K) redetermination of a previously reported room-temperature structure [Trotter (1959). Acta Cryst. 12, 237-242].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025267/ac6129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025267/ac6129Isup2.hkl
Contains datablock I

CCDC reference: 255937

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.148
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.859 0.984 Tmin' and Tmax expected: 0.961 0.984 RR' = 0.894 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.39
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997-1999); cell refinement: SAINT-Plus; data reduction: SAINT-Plus (Bruker, 1997-1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

9-Nitroanthracene top
Crystal data top
C14H9NO2F(000) = 464
Mr = 223.22Dx = 1.440 Mg m3
Monoclinic, P21/cMelting point: 417.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.5117 (7) ÅCell parameters from 5299 reflections
b = 13.5401 (9) Åθ = 2.5–28.3°
c = 7.4285 (5) ŵ = 0.10 mm1
β = 103.197 (1)°T = 100 K
V = 1029.37 (12) Å3Needle, yellow
Z = 40.40 × 0.16 × 0.16 mm
Data collection top
Bruker SMART APEX
diffractometer
2545 independent reflections
Radiation source: sealed tube2182 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1414
Tmin = 0.859, Tmax = 0.984k = 1818
10391 measured reflectionsl = 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.28 w = 1/[σ2(Fo2) + (0.0913P)2]
where P = (Fo2 + 2Fc2)/3
2545 reflections(Δ/σ)max = 0.017
154 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. The H atoms were included in calculated positions with a C—H distance of 0.95 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.

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
N10.24090 (8)0.46836 (7)0.10102 (11)0.0221 (2)
O10.23713 (11)0.50593 (6)0.04888 (11)0.0432 (3)
O20.22982 (9)0.51554 (6)0.23658 (11)0.0331 (3)
C90.26010 (10)0.36082 (7)0.12056 (13)0.0182 (2)
C110.37933 (9)0.32746 (7)0.22736 (12)0.0182 (2)
C10.48392 (10)0.39049 (8)0.31617 (14)0.0222 (2)
H1A0.47370.46010.30660.027*
C20.59801 (10)0.35137 (8)0.41437 (14)0.0246 (3)
H2A0.66730.39420.47080.030*
C30.61518 (10)0.24761 (9)0.43381 (14)0.0241 (3)
H3A0.69500.22160.50440.029*
C40.51759 (10)0.18554 (8)0.35158 (13)0.0219 (3)
H4A0.52980.11620.36600.026*
C120.39697 (9)0.22272 (7)0.24383 (13)0.0181 (2)
C100.29670 (9)0.15963 (7)0.15600 (13)0.0197 (2)
H10A0.30980.09030.16740.024*
C140.17801 (10)0.19513 (8)0.05222 (13)0.0192 (2)
C50.07487 (10)0.13035 (8)0.03400 (14)0.0239 (3)
H5A0.08710.06090.02190.029*
C60.04046 (10)0.16643 (9)0.13311 (14)0.0272 (3)
H6A0.10790.12220.18990.033*
C70.06078 (10)0.27020 (9)0.15234 (14)0.0258 (3)
H7A0.14210.29460.22130.031*
C80.03475 (9)0.33483 (8)0.07323 (13)0.0223 (3)
H8A0.01980.40390.08790.027*
C130.15751 (9)0.29959 (8)0.03180 (13)0.0185 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0211 (4)0.0213 (5)0.0218 (5)0.0006 (3)0.0004 (3)0.0006 (3)
O10.0755 (7)0.0266 (5)0.0268 (5)0.0093 (4)0.0101 (5)0.0077 (3)
O20.0465 (5)0.0222 (4)0.0312 (5)0.0004 (3)0.0099 (4)0.0074 (3)
C90.0193 (5)0.0188 (5)0.0163 (5)0.0004 (4)0.0039 (4)0.0001 (3)
C110.0174 (5)0.0230 (5)0.0144 (5)0.0009 (4)0.0041 (4)0.0007 (4)
C10.0216 (5)0.0235 (5)0.0207 (5)0.0036 (4)0.0032 (4)0.0013 (4)
C20.0201 (5)0.0329 (6)0.0199 (5)0.0057 (4)0.0024 (4)0.0039 (4)
C30.0182 (5)0.0361 (6)0.0174 (5)0.0043 (4)0.0026 (4)0.0019 (4)
C40.0215 (5)0.0254 (5)0.0189 (5)0.0055 (4)0.0049 (4)0.0002 (4)
C120.0184 (5)0.0224 (5)0.0145 (5)0.0005 (4)0.0056 (4)0.0003 (4)
C100.0214 (5)0.0199 (5)0.0188 (5)0.0007 (4)0.0064 (4)0.0013 (4)
C140.0186 (5)0.0243 (5)0.0158 (5)0.0032 (4)0.0061 (4)0.0031 (4)
C50.0239 (5)0.0261 (5)0.0232 (5)0.0061 (4)0.0087 (4)0.0058 (4)
C60.0204 (5)0.0403 (6)0.0208 (5)0.0098 (5)0.0046 (4)0.0092 (4)
C70.0176 (5)0.0408 (7)0.0183 (5)0.0004 (4)0.0030 (4)0.0037 (4)
C80.0194 (5)0.0293 (5)0.0178 (5)0.0023 (4)0.0031 (4)0.0008 (4)
C130.0170 (5)0.0243 (5)0.0149 (5)0.0007 (4)0.0049 (4)0.0019 (4)
Geometric parameters (Å, º) top
N1—O11.2166 (11)C4—H4A0.9500
N1—O21.2203 (11)C12—C101.3973 (13)
N1—C91.4728 (13)C10—C141.3939 (14)
C9—C111.3964 (13)C10—H10A0.9500
C9—C131.4001 (13)C14—C51.4276 (13)
C11—C11.4287 (13)C14—C131.4334 (14)
C11—C121.4318 (14)C5—C61.3576 (14)
C1—C21.3607 (14)C5—H5A0.9500
C1—H1A0.9500C6—C71.4234 (17)
C2—C31.4196 (16)C6—H6A0.9500
C2—H2A0.9500C7—C81.3602 (14)
C3—C41.3585 (15)C7—H7A0.9500
C3—H3A0.9500C8—C131.4290 (13)
C4—C121.4278 (13)C8—H8A0.9500
O1—N1—O2123.17 (9)C4—C12—C11118.57 (9)
O1—N1—C9118.60 (8)C14—C10—C12122.13 (9)
O2—N1—C9118.23 (8)C14—C10—H10A118.9
C11—C9—C13124.81 (9)C12—C10—H10A118.9
C11—C9—N1117.44 (8)C10—C14—C5121.90 (10)
C13—C9—N1117.75 (8)C10—C14—C13119.52 (9)
C9—C11—C1124.43 (9)C5—C14—C13118.58 (9)
C9—C11—C12116.80 (9)C6—C5—C14120.99 (10)
C1—C11—C12118.76 (9)C6—C5—H5A119.5
C2—C1—C11120.41 (10)C14—C5—H5A119.5
C2—C1—H1A119.8C5—C6—C7120.31 (9)
C11—C1—H1A119.8C5—C6—H6A119.8
C1—C2—C3121.05 (9)C7—C6—H6A119.8
C1—C2—H2A119.5C8—C7—C6120.84 (10)
C3—C2—H2A119.5C8—C7—H7A119.6
C4—C3—C2120.07 (9)C6—C7—H7A119.6
C4—C3—H3A120.0C7—C8—C13120.44 (10)
C2—C3—H3A120.0C7—C8—H8A119.8
C3—C4—C12121.11 (9)C13—C8—H8A119.8
C3—C4—H4A119.4C9—C13—C8124.18 (10)
C12—C4—H4A119.4C9—C13—C14116.96 (9)
C10—C12—C4121.66 (9)C8—C13—C14118.84 (9)
C10—C12—C11119.77 (8)
O1—N1—C9—C11110.44 (11)C4—C12—C10—C14179.26 (8)
O2—N1—C9—C1169.40 (12)C11—C12—C10—C140.39 (14)
O1—N1—C9—C1369.91 (12)C12—C10—C14—C5178.66 (8)
O2—N1—C9—C13110.25 (10)C12—C10—C14—C130.85 (14)
C13—C9—C11—C1179.45 (9)C10—C14—C5—C6179.39 (9)
N1—C9—C11—C10.93 (14)C13—C14—C5—C60.13 (14)
C13—C9—C11—C120.87 (14)C14—C5—C6—C70.20 (15)
N1—C9—C11—C12179.50 (8)C5—C6—C7—C80.43 (16)
C9—C11—C1—C2178.52 (9)C6—C7—C8—C130.30 (15)
C12—C11—C1—C20.03 (14)C11—C9—C13—C8178.34 (9)
C11—C1—C2—C31.13 (15)N1—C9—C13—C81.28 (14)
C1—C2—C3—C40.94 (16)C11—C9—C13—C140.43 (14)
C2—C3—C4—C120.38 (15)N1—C9—C13—C14179.95 (8)
C3—C4—C12—C10178.90 (9)C7—C8—C13—C9178.78 (9)
C3—C4—C12—C111.45 (14)C7—C8—C13—C140.03 (14)
C9—C11—C12—C100.45 (13)C10—C14—C13—C90.44 (13)
C1—C11—C12—C10179.11 (8)C5—C14—C13—C9179.08 (8)
C9—C11—C12—C4179.90 (8)C10—C14—C13—C8179.28 (8)
C1—C11—C12—C41.23 (13)C5—C14—C13—C80.24 (13)
 

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