Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018766/cf6012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018766/cf6012Isup2.hkl |
CCDC reference: 155855
Key indicators
- Single-crystal X-ray study
- T = 168 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.110
- Data-to-parameter ratio = 10.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.096 Value of mu given = 0.100 ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.780 0.980 Tmin' and Tmax expected: 0.929 0.974 RR' = 0.834 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
A mixture of isomers was obtained by nitration of phenanthrene with nitric acid in benzene following the method of Heaney et al. (1965). After chromatography of the mixture, 4-nitrophenanthrene was obtained pure and was crystallized as yellow prisms from hexane.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT and Xtal3.4 ADDREF SORTRF (Hall et al., 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: Xtal3.4 CRYLSQ; molecular graphics: Xtal3.4; software used to prepare material for publication: Xtal3.4 BONDLA CIFIO.
Fig. 1. The molecular structure of 4-nitrophenanthrene showing 50% probability displacement ellipsoids. |
C14H9NO2 | F(000) = 464 |
Mr = 223.23 | Dx = 1.41 Mg m−3 |
Monoclinic, P21/c | Melting point: 81.5-82.0 °C K |
Hall symbol: -p 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.061 (2) Å | Cell parameters from 5719 reflections |
b = 12.449 (3) Å | θ = 2.5–26.4° |
c = 11.132 (3) Å | µ = 0.10 mm−1 |
β = 109.73 (1)° | T = 168 K |
V = 1051.5 (5) Å3 | Prism, pale yellow |
Z = 4 | 0.72 × 0.46 × 0.26 mm |
Bruker SMART P4 diffractometer | 1945 reflections with F2 > 0 |
Detector resolution: 8.192 pixels mm-1 | Rint = 0.028 |
ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = 0→10 |
Tmin = 0.78, Tmax = 0.98 | k = 0→15 |
13110 measured reflections | l = −13→13 |
2135 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.049 | All H-atom parameters refined |
wR(F2) = 0.11 | w = 1/[σ2(Fo2) + (0.06Fo2)2 + 0.5Fo2] |
S = 1.03 | (Δ/σ)max < 0.001 |
1943 reflections | Δρmax = 0.29 e Å−3 |
190 parameters | Δρmin = −0.22 e Å−3 |
C14H9NO2 | V = 1051.5 (5) Å3 |
Mr = 223.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.061 (2) Å | µ = 0.10 mm−1 |
b = 12.449 (3) Å | T = 168 K |
c = 11.132 (3) Å | 0.72 × 0.46 × 0.26 mm |
β = 109.73 (1)° |
Bruker SMART P4 diffractometer | 2135 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1945 reflections with F2 > 0 |
Tmin = 0.78, Tmax = 0.98 | Rint = 0.028 |
13110 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.11 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.29 e Å−3 |
1943 reflections | Δρmin = −0.22 e Å−3 |
190 parameters |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. |
x | y | z | Uiso*/Ueq | ||
N | 0.75013 (19) | 0.30657 (11) | 0.08041 (14) | 0.0377 (7) | |
O1 | 0.85095 (16) | 0.25134 (10) | 0.04507 (13) | 0.0487 (7) | |
O2 | 0.79833 (18) | 0.38205 (11) | 0.15553 (15) | 0.0598 (8) | |
C1 | 0.2069 (2) | 0.25122 (14) | −0.10627 (17) | 0.0390 (8) | |
C2 | 0.2871 (3) | 0.34201 (15) | −0.12965 (17) | 0.0426 (9) | |
C3 | 0.4662 (2) | 0.35883 (14) | −0.06233 (17) | 0.0384 (8) | |
C4 | 0.5578 (2) | 0.28431 (12) | 0.02590 (15) | 0.0319 (7) | |
C5 | 0.7442 (2) | 0.12262 (14) | 0.24429 (16) | 0.0361 (8) | |
C6 | 0.8270 (2) | 0.04098 (15) | 0.32569 (17) | 0.0417 (9) | |
C7 | 0.7421 (2) | −0.05733 (14) | 0.32257 (16) | 0.0396 (8) | |
C8 | 0.5714 (2) | −0.06978 (13) | 0.24207 (16) | 0.0347 (8) | |
C9 | 0.3012 (2) | −0.00034 (13) | 0.07995 (16) | 0.0345 (8) | |
C10 | 0.2131 (2) | 0.07775 (14) | 0.00120 (16) | 0.0361 (8) | |
C4a | 0.4819 (2) | 0.19059 (11) | 0.05832 (14) | 0.0275 (7) | |
C4b | 0.5727 (2) | 0.11059 (12) | 0.15396 (14) | 0.0278 (7) | |
C8a | 0.4823 (2) | 0.01289 (12) | 0.15837 (14) | 0.0288 (7) | |
C10a | 0.2999 (2) | 0.17500 (12) | −0.01412 (15) | 0.0316 (7) | |
H1 | 0.084 (3) | 0.2316 (15) | −0.1558 (18) | 0.043 (5)* | |
H2 | 0.223 (3) | 0.3906 (17) | −0.1983 (19) | 0.053 (6)* | |
H3 | 0.525 (2) | 0.4204 (16) | −0.0779 (17) | 0.045 (5)* | |
H5 | 0.803 (3) | 0.1915 (16) | 0.2473 (19) | 0.053 (6)* | |
H6 | 0.949 (3) | 0.0541 (15) | 0.3881 (18) | 0.048 (5)* | |
H7 | 0.800 (2) | −0.1151 (16) | 0.3780 (18) | 0.050 (5)* | |
H8 | 0.506 (2) | −0.1367 (15) | 0.2402 (18) | 0.041 (5)* | |
H9 | 0.248 (2) | −0.0656 (16) | 0.0863 (18) | 0.045 (5)* | |
H10 | 0.092 (3) | 0.0680 (16) | −0.0524 (19) | 0.053 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.0414 (8) | 0.0293 (7) | 0.0454 (8) | −0.0073 (6) | 0.0185 (7) | 0.0006 (6) |
O1 | 0.0415 (7) | 0.0457 (7) | 0.0650 (9) | −0.0015 (6) | 0.0261 (6) | −0.0029 (6) |
O2 | 0.0559 (9) | 0.0433 (8) | 0.0777 (10) | −0.0171 (6) | 0.0194 (7) | −0.0218 (7) |
C1 | 0.0337 (9) | 0.0437 (10) | 0.0396 (9) | 0.0094 (8) | 0.0122 (7) | 0.0005 (8) |
C2 | 0.0525 (11) | 0.0386 (10) | 0.0392 (9) | 0.0151 (8) | 0.0188 (8) | 0.0088 (8) |
C3 | 0.0509 (10) | 0.0282 (8) | 0.0429 (9) | 0.0036 (7) | 0.0250 (8) | 0.0041 (7) |
C4 | 0.0355 (9) | 0.0275 (8) | 0.0363 (9) | −0.0009 (6) | 0.0169 (7) | −0.0028 (7) |
C5 | 0.0341 (9) | 0.0362 (9) | 0.0371 (9) | −0.0065 (7) | 0.0108 (7) | 0.0026 (7) |
C6 | 0.0343 (9) | 0.0514 (11) | 0.0370 (9) | 0.0010 (8) | 0.0090 (7) | 0.0061 (8) |
C7 | 0.0474 (10) | 0.0380 (9) | 0.0362 (9) | 0.0109 (8) | 0.0179 (8) | 0.0074 (8) |
C8 | 0.0462 (10) | 0.0262 (8) | 0.0384 (9) | −0.0002 (7) | 0.0231 (8) | 0.0007 (7) |
C9 | 0.0354 (9) | 0.0289 (8) | 0.0439 (9) | −0.0083 (7) | 0.0195 (7) | −0.0051 (7) |
C10 | 0.0276 (8) | 0.0385 (9) | 0.0439 (9) | −0.0041 (7) | 0.0142 (7) | −0.0063 (8) |
C4a | 0.0321 (8) | 0.0234 (7) | 0.0301 (8) | −0.0007 (6) | 0.0146 (6) | −0.0042 (6) |
C4b | 0.0292 (8) | 0.0275 (8) | 0.0296 (7) | −0.0008 (6) | 0.0137 (6) | −0.0026 (6) |
C8a | 0.0338 (8) | 0.0261 (7) | 0.0312 (8) | −0.0015 (6) | 0.0170 (6) | −0.0030 (6) |
C10a | 0.0318 (8) | 0.0315 (8) | 0.0338 (8) | 0.0034 (6) | 0.0140 (7) | −0.0028 (7) |
N—O1 | 1.226 (2) | C6—C7 | 1.397 (3) |
N—O2 | 1.230 (2) | C6—H6 | 1.009 (18) |
N—C4 | 1.488 (2) | C7—C8 | 1.374 (2) |
C1—C2 | 1.370 (3) | C7—H7 | 0.96 (2) |
C1—C10a | 1.413 (2) | C8—C8a | 1.411 (2) |
C1—H1 | 0.990 (18) | C8—H8 | 0.98 (2) |
C2—C3 | 1.400 (3) | C9—C10 | 1.341 (2) |
C2—H2 | 0.976 (19) | C9—C8a | 1.435 (2) |
C3—C4 | 1.371 (2) | C9—H9 | 0.93 (2) |
C3—H3 | 0.95 (2) | C10—C10a | 1.437 (2) |
C4—C4a | 1.420 (2) | C10—H10 | 0.966 (18) |
C5—C6 | 1.375 (2) | C4a—C4b | 1.461 (2) |
C5—C4b | 1.417 (2) | C4a—C10a | 1.428 (2) |
C5—H5 | 0.98 (2) | C4b—C8a | 1.427 (2) |
O1—N—O2 | 123.69 (15) | C8—C7—H7 | 119.8 (11) |
O1—N—C4 | 118.49 (13) | C7—C8—C8a | 121.54 (15) |
O2—N—C4 | 117.77 (15) | C7—C8—H8 | 121.5 (10) |
C2—C1—C10a | 121.55 (15) | C8a—C8—H8 | 117.0 (10) |
C2—C1—H1 | 123.1 (11) | C10—C9—C8a | 121.33 (15) |
C10a—C1—H1 | 115.2 (11) | C10—C9—H9 | 121.6 (10) |
C1—C2—C3 | 119.29 (16) | C8a—C9—H9 | 117.0 (10) |
C1—C2—H2 | 120.0 (12) | C9—C10—C10a | 121.10 (14) |
C3—C2—H2 | 120.4 (12) | C9—C10—H10 | 121.0 (12) |
C2—C3—C4 | 119.40 (17) | C10a—C10—H10 | 117.7 (12) |
C2—C3—H3 | 120.9 (10) | C4—C4a—C4b | 126.35 (13) |
C4—C3—H3 | 119.7 (10) | C4—C4a—C10a | 114.63 (12) |
N—C4—C3 | 113.66 (15) | C4b—C4a—C10a | 119.01 (14) |
N—C4—C4a | 121.92 (12) | C5—C4b—C4a | 125.02 (14) |
C3—C4—C4a | 124.32 (14) | C5—C4b—C8a | 116.94 (13) |
C6—C5—C4b | 122.00 (16) | C4a—C4b—C8a | 118.04 (12) |
C6—C5—H5 | 120.2 (10) | C8—C8a—C9 | 120.31 (15) |
C4b—C5—H5 | 117.8 (10) | C8—C8a—C4b | 119.47 (13) |
C5—C6—C7 | 120.42 (15) | C9—C8a—C4b | 120.21 (13) |
C5—C6—H6 | 118.6 (11) | C1—C10a—C10 | 119.43 (13) |
C7—C6—H6 | 121.0 (11) | C1—C10a—C4a | 120.73 (15) |
C6—C7—C8 | 119.30 (15) | C10—C10a—C4a | 119.74 (13) |
C6—C7—H7 | 120.8 (11) |
Experimental details
Crystal data | |
Chemical formula | C14H9NO2 |
Mr | 223.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 168 |
a, b, c (Å) | 8.061 (2), 12.449 (3), 11.132 (3) |
β (°) | 109.73 (1) |
V (Å3) | 1051.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.72 × 0.46 × 0.26 |
Data collection | |
Diffractometer | Bruker SMART P4 diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.78, 0.98 |
No. of measured, independent and observed (F2 > 0) reflections | 13110, 2135, 1945 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.11, 1.03 |
No. of reflections | 1943 |
No. of parameters | 190 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.29, −0.22 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1996), SAINT and Xtal3.4 ADDREF SORTRF (Hall et al., 1995), SIR92 (Altomare et al., 1994), Xtal3.4 CRYLSQ, Xtal3.4 BONDLA CIFIO.
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As part of a study directed towards relating NMR chemical shifts to the degree of conjugation of substituents in phenanthrene, the structure of 4-nitrophenanthrene, (I), has been determined. The angle between the NO2 and phenanthrene planes indicates that there will be reduced conjugation. This angle of 72.2 (7)° can be compared with the value of 60.7° obtained by calculation using SPARTAN (Wavefunction, 1995).