In the title compound, C
10H
11NO
5, all bond lengths and angles show normal values. Weak intermolecular O—H
O hydrogen bonds form centrosymmetric dimers, which are further linked by π–π interactions into ladders extending along the
a axis.
Supporting information
CCDC reference: 293872
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.166
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2 .. 2.76 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2001); software used to prepare material for publication: SHELXTL-NT.
1-propyl 5-nitrosalicylate
top
Crystal data top
C10H11NO5 | F(000) = 472 |
Mr = 225.20 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 626 reflections |
a = 5.1084 (8) Å | θ = 2.9–19.6° |
b = 11.5966 (18) Å | µ = 0.11 mm−1 |
c = 18.166 (3) Å | T = 292 K |
β = 94.018 (3)° | Block, colourless |
V = 1073.5 (3) Å3 | 0.20 × 0.16 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2346 independent reflections |
Radiation source: fine-focus sealed tube | 1086 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.978, Tmax = 0.989 | k = −14→14 |
6263 measured reflections | l = −21→23 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0695P)2] where P = (Fo2 + 2Fc2)/3 |
2346 reflections | (Δ/σ)max < 0.001 |
150 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4602 (5) | 0.1332 (2) | 0.40666 (13) | 0.0488 (6) | |
C2 | 0.4666 (5) | 0.0179 (2) | 0.38380 (14) | 0.0552 (7) | |
C3 | 0.6364 (6) | −0.0155 (2) | 0.33112 (15) | 0.0652 (8) | |
H3 | 0.6429 | −0.0925 | 0.3169 | 0.078* | |
C4 | 0.7935 (6) | 0.0634 (3) | 0.29997 (15) | 0.0638 (8) | |
H4 | 0.9058 | 0.0409 | 0.2645 | 0.077* | |
C5 | 0.7827 (5) | 0.1769 (2) | 0.32212 (14) | 0.0560 (7) | |
C6 | 0.6214 (5) | 0.2120 (2) | 0.37442 (14) | 0.0544 (7) | |
H6 | 0.6195 | 0.2890 | 0.3886 | 0.065* | |
C7 | 0.2856 (5) | 0.1677 (2) | 0.46351 (14) | 0.0534 (7) | |
C8 | 0.1412 (6) | 0.3146 (3) | 0.54101 (17) | 0.0806 (10) | |
H8A | 0.1330 | 0.2574 | 0.5797 | 0.097* | |
H8B | −0.0343 | 0.3257 | 0.5181 | 0.097* | |
C9 | 0.2444 (6) | 0.4249 (3) | 0.57238 (18) | 0.0836 (10) | |
H9A | 0.2701 | 0.4778 | 0.5322 | 0.100* | |
H9B | 0.1135 | 0.4583 | 0.6022 | 0.100* | |
C10 | 0.4913 (7) | 0.4147 (3) | 0.61775 (19) | 0.1039 (12) | |
H10A | 0.4676 | 0.3638 | 0.6585 | 0.156* | |
H10B | 0.5441 | 0.4893 | 0.6361 | 0.156* | |
H10C | 0.6243 | 0.3841 | 0.5884 | 0.156* | |
H1 | 0.214 (8) | −0.027 (3) | 0.4446 (19) | 0.138 (15)* | |
N1 | 0.9513 (5) | 0.2619 (3) | 0.28870 (14) | 0.0765 (8) | |
O1 | 0.3162 (4) | −0.06473 (16) | 0.41089 (12) | 0.0731 (6) | |
O2 | 0.1262 (4) | 0.10288 (17) | 0.48777 (11) | 0.0713 (6) | |
O3 | 0.3172 (3) | 0.27576 (16) | 0.48620 (10) | 0.0665 (6) | |
O4 | 0.9513 (6) | 0.3599 (2) | 0.31125 (15) | 0.1270 (11) | |
O5 | 1.0843 (5) | 0.2307 (2) | 0.23965 (14) | 0.1066 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0492 (15) | 0.0526 (16) | 0.0449 (15) | 0.0029 (12) | 0.0064 (12) | 0.0024 (12) |
C2 | 0.0563 (17) | 0.0551 (17) | 0.0542 (17) | 0.0019 (13) | 0.0054 (14) | 0.0036 (13) |
C3 | 0.077 (2) | 0.0544 (17) | 0.0647 (18) | 0.0087 (15) | 0.0096 (17) | −0.0061 (14) |
C4 | 0.0646 (18) | 0.078 (2) | 0.0508 (17) | 0.0124 (15) | 0.0150 (14) | −0.0005 (15) |
C5 | 0.0587 (17) | 0.0623 (18) | 0.0480 (16) | 0.0002 (14) | 0.0114 (14) | 0.0064 (13) |
C6 | 0.0610 (18) | 0.0537 (16) | 0.0492 (16) | −0.0011 (13) | 0.0095 (14) | −0.0018 (12) |
C7 | 0.0521 (16) | 0.0565 (17) | 0.0517 (17) | 0.0014 (14) | 0.0042 (14) | 0.0011 (13) |
C8 | 0.0678 (19) | 0.089 (2) | 0.089 (2) | 0.0023 (18) | 0.0344 (18) | −0.0235 (19) |
C9 | 0.081 (2) | 0.091 (2) | 0.081 (2) | 0.0090 (19) | 0.020 (2) | −0.0215 (19) |
C10 | 0.075 (2) | 0.145 (3) | 0.091 (3) | −0.003 (2) | 0.004 (2) | −0.020 (2) |
N1 | 0.0820 (19) | 0.086 (2) | 0.0645 (17) | −0.0041 (16) | 0.0285 (15) | 0.0091 (15) |
O1 | 0.0797 (15) | 0.0529 (12) | 0.0888 (16) | −0.0054 (10) | 0.0215 (13) | 0.0024 (11) |
O2 | 0.0631 (12) | 0.0756 (13) | 0.0780 (14) | −0.0139 (11) | 0.0253 (10) | −0.0029 (11) |
O3 | 0.0725 (13) | 0.0613 (12) | 0.0691 (13) | −0.0001 (10) | 0.0295 (11) | −0.0080 (10) |
O4 | 0.171 (3) | 0.0816 (18) | 0.140 (2) | −0.0392 (18) | 0.091 (2) | −0.0133 (16) |
O5 | 0.120 (2) | 0.1158 (19) | 0.0921 (17) | −0.0065 (15) | 0.0640 (16) | 0.0057 (14) |
Geometric parameters (Å, º) top
C1—C6 | 1.387 (3) | C8—O3 | 1.459 (3) |
C1—C2 | 1.400 (3) | C8—C9 | 1.482 (4) |
C1—C7 | 1.467 (3) | C8—H8A | 0.9700 |
C2—O1 | 1.343 (3) | C8—H8B | 0.9700 |
C2—C3 | 1.391 (4) | C9—C10 | 1.462 (4) |
C3—C4 | 1.366 (4) | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
C4—C5 | 1.379 (4) | C10—H10A | 0.9600 |
C4—H4 | 0.9300 | C10—H10B | 0.9600 |
C5—C6 | 1.362 (3) | C10—H10C | 0.9600 |
C5—N1 | 1.468 (4) | N1—O4 | 1.208 (3) |
C6—H6 | 0.9300 | N1—O5 | 1.213 (3) |
C7—O2 | 1.214 (3) | O1—H1 | 0.94 (4) |
C7—O3 | 1.325 (3) | | |
| | | |
C6—C1—C2 | 118.5 (2) | O3—C8—H8A | 110.1 |
C6—C1—C7 | 121.7 (2) | C9—C8—H8A | 110.1 |
C2—C1—C7 | 119.8 (2) | O3—C8—H8B | 110.1 |
O1—C2—C3 | 116.9 (3) | C9—C8—H8B | 110.1 |
O1—C2—C1 | 123.1 (2) | H8A—C8—H8B | 108.4 |
C3—C2—C1 | 119.9 (2) | C10—C9—C8 | 114.6 (3) |
C4—C3—C2 | 120.7 (3) | C10—C9—H9A | 108.6 |
C4—C3—H3 | 119.6 | C8—C9—H9A | 108.6 |
C2—C3—H3 | 119.6 | C10—C9—H9B | 108.6 |
C3—C4—C5 | 118.8 (3) | C8—C9—H9B | 108.6 |
C3—C4—H4 | 120.6 | H9A—C9—H9B | 107.6 |
C5—C4—H4 | 120.6 | C9—C10—H10A | 109.5 |
C6—C5—C4 | 121.8 (3) | C9—C10—H10B | 109.5 |
C6—C5—N1 | 119.3 (3) | H10A—C10—H10B | 109.5 |
C4—C5—N1 | 118.9 (3) | C9—C10—H10C | 109.5 |
C5—C6—C1 | 120.2 (2) | H10A—C10—H10C | 109.5 |
C5—C6—H6 | 119.9 | H10B—C10—H10C | 109.5 |
C1—C6—H6 | 119.9 | O4—N1—O5 | 122.9 (3) |
O2—C7—O3 | 122.9 (2) | O4—N1—C5 | 118.5 (3) |
O2—C7—C1 | 122.9 (2) | O5—N1—C5 | 118.6 (3) |
O3—C7—C1 | 114.3 (2) | C2—O1—H1 | 105 (2) |
O3—C8—C9 | 108.0 (2) | C7—O3—C8 | 115.9 (2) |
| | | |
C6—C1—C2—O1 | −179.2 (2) | C6—C1—C7—O2 | 173.2 (2) |
C7—C1—C2—O1 | 0.9 (4) | C2—C1—C7—O2 | −6.8 (4) |
C6—C1—C2—C3 | 1.4 (4) | C6—C1—C7—O3 | −6.9 (3) |
C7—C1—C2—C3 | −178.5 (2) | C2—C1—C7—O3 | 173.1 (2) |
O1—C2—C3—C4 | 179.1 (2) | O3—C8—C9—C10 | −68.4 (4) |
C1—C2—C3—C4 | −1.5 (4) | C6—C5—N1—O4 | 3.5 (4) |
C2—C3—C4—C5 | 0.5 (4) | C4—C5—N1—O4 | −176.0 (3) |
C3—C4—C5—C6 | 0.5 (4) | C6—C5—N1—O5 | −176.4 (3) |
C3—C4—C5—N1 | −180.0 (3) | C4—C5—N1—O5 | 4.0 (4) |
C4—C5—C6—C1 | −0.6 (4) | O2—C7—O3—C8 | −2.0 (4) |
N1—C5—C6—C1 | 179.9 (2) | C1—C7—O3—C8 | 178.1 (2) |
C2—C1—C6—C5 | −0.4 (4) | C9—C8—O3—C7 | 166.7 (2) |
C7—C1—C6—C5 | 179.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.94 (4) | 1.77 (4) | 2.619 (3) | 149 (3) |
O1—H1···O2i | 0.94 (4) | 2.37 (4) | 3.045 (3) | 129 (3) |
Symmetry code: (i) −x, −y, −z+1. |