In the crystal structure of the title compound, C
12H
9NO
4, the disordered pyran ring adopts a half-chair conformation. Weak intermolecular C—H
O hydrogen bonds link molecules into centrosymmetric dimers, which generate
(6),
(10) and
(14) rings. In addition, π–π stacking interactions are present.
Supporting information
CCDC reference: 255924
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.125
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C4A
PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C2 - C6 ... 1.32 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
7-Nitro-2,3-dihydro-1
H-cyclopenta[
b]chromen-1-one
top
Crystal data top
C12H9NO4 | F(000) = 480 |
Mr = 231.20 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6400 reflections |
a = 6.0584 (11) Å | θ = 2.5–22.4° |
b = 19.717 (4) Å | µ = 0.11 mm−1 |
c = 8.9513 (16) Å | T = 293 K |
β = 98.257 (4)° | Block, yellow |
V = 1058.2 (3) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1850 independent reflections |
Radiation source: fine-focus sealed tube | 1165 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→6 |
Tmin = 0.978, Tmax = 0.989 | k = −23→20 |
4356 measured reflections | l = −10→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0544P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
1850 reflections | Δρmax = 0.17 e Å−3 |
183 parameters | Δρmin = −0.18 e Å−3 |
5 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: none |
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 | Occ. (<1) |
O1 | 0.4651 (3) | 0.83740 (8) | 0.77807 (19) | 0.0625 (6) | |
O2 | −0.1177 (3) | 0.88831 (9) | 1.0617 (2) | 0.0688 (6) | |
O3 | 0.8800 (4) | 1.10283 (10) | 0.5657 (2) | 0.0920 (7) | |
O4 | 0.6501 (3) | 1.14603 (9) | 0.7013 (2) | 0.0784 (6) | |
N | 0.7345 (4) | 1.09737 (11) | 0.6467 (2) | 0.0636 (6) | |
C1 | 0.0167 (4) | 0.85576 (13) | 1.0037 (3) | 0.0542 (7) | |
C2 | 0.1961 (4) | 0.88384 (12) | 0.9283 (3) | 0.0563 (7) | |
C3 | 0.3602 (8) | 0.82608 (17) | 0.9093 (5) | 0.0518 (14) | 0.720 (9) |
H3A | 0.4713 | 0.8212 | 0.9997 | 0.078* | 0.720 (9) |
C4 | 0.201 (2) | 0.7664 (3) | 0.8916 (16) | 0.081 (4) | 0.720 (9) |
H4A | 0.2807 | 0.7249 | 0.9224 | 0.121* | 0.720 (9) |
H4B | 0.1347 | 0.7618 | 0.7869 | 0.121* | 0.720 (9) |
C5 | 0.019 (3) | 0.7794 (2) | 0.9913 (18) | 0.072 (4) | 0.720 (9) |
H5A | −0.1242 | 0.7623 | 0.9440 | 0.109* | 0.720 (9) |
H5B | 0.0568 | 0.7584 | 1.0897 | 0.109* | 0.720 (9) |
C3A | 0.2518 (12) | 0.8261 (5) | 0.8243 (15) | 0.063 (4) | 0.280 (9) |
H3AA | 0.1373 | 0.8237 | 0.7353 | 0.094* | 0.280 (9) |
C4A | 0.248 (6) | 0.7617 (10) | 0.916 (4) | 0.078 (9) | 0.280 (9) |
H4AA | 0.3906 | 0.7530 | 0.9772 | 0.118* | 0.280 (9) |
H4AB | 0.2044 | 0.7227 | 0.8527 | 0.118* | 0.280 (9) |
C5A | 0.068 (6) | 0.7808 (3) | 1.013 (4) | 0.054 (6) | 0.280 (9) |
H5AA | −0.0671 | 0.7553 | 0.9798 | 0.081* | 0.280 (9) |
H5AB | 0.1188 | 0.7686 | 1.1177 | 0.081* | 0.280 (9) |
C6 | 0.2374 (4) | 0.94652 (12) | 0.8885 (3) | 0.0467 (6) | |
H6A | 0.1522 | 0.9825 | 0.9157 | 0.056* | |
C7 | 0.4879 (4) | 1.02246 (12) | 0.7660 (3) | 0.0481 (6) | |
H7A | 0.4190 | 1.0607 | 0.7990 | 0.058* | |
C8 | 0.6601 (4) | 1.02938 (12) | 0.6814 (3) | 0.0496 (6) | |
C9 | 0.7598 (4) | 0.97373 (13) | 0.6268 (3) | 0.0602 (7) | |
H9A | 0.8735 | 0.9793 | 0.5683 | 0.072* | |
C10 | 0.6900 (4) | 0.90974 (13) | 0.6596 (3) | 0.0593 (7) | |
H10A | 0.7549 | 0.8719 | 0.6217 | 0.071* | |
C11 | 0.5241 (4) | 0.90166 (12) | 0.7483 (3) | 0.0473 (6) | |
C12 | 0.4181 (4) | 0.95823 (11) | 0.8018 (2) | 0.0449 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0739 (13) | 0.0435 (11) | 0.0768 (13) | 0.0021 (9) | 0.0342 (10) | −0.0077 (8) |
O2 | 0.0674 (12) | 0.0591 (12) | 0.0879 (13) | 0.0027 (10) | 0.0380 (11) | −0.0003 (10) |
O3 | 0.1031 (17) | 0.0844 (16) | 0.1007 (16) | −0.0194 (12) | 0.0565 (14) | 0.0038 (12) |
O4 | 0.0886 (15) | 0.0490 (12) | 0.1032 (15) | 0.0041 (11) | 0.0325 (12) | 0.0105 (11) |
N | 0.0667 (16) | 0.0626 (16) | 0.0631 (15) | −0.0032 (12) | 0.0148 (13) | 0.0079 (12) |
C1 | 0.0528 (16) | 0.0506 (16) | 0.0615 (16) | −0.0038 (13) | 0.0161 (14) | −0.0035 (13) |
C2 | 0.0599 (17) | 0.0403 (15) | 0.0733 (17) | −0.0028 (12) | 0.0255 (14) | −0.0064 (13) |
C3 | 0.053 (3) | 0.041 (2) | 0.065 (3) | 0.0046 (19) | 0.018 (2) | 0.005 (2) |
C4 | 0.092 (7) | 0.026 (4) | 0.135 (9) | −0.001 (3) | 0.054 (7) | −0.009 (4) |
C5 | 0.073 (7) | 0.052 (4) | 0.098 (8) | −0.004 (3) | 0.034 (6) | −0.013 (4) |
C3A | 0.051 (7) | 0.056 (7) | 0.081 (9) | 0.007 (6) | 0.010 (6) | −0.005 (6) |
C4A | 0.072 (12) | 0.087 (18) | 0.082 (11) | 0.012 (10) | 0.032 (9) | 0.033 (10) |
C5A | 0.055 (13) | 0.040 (9) | 0.070 (9) | −0.024 (6) | 0.013 (9) | 0.008 (8) |
C6 | 0.0483 (15) | 0.0405 (14) | 0.0530 (14) | 0.0067 (11) | 0.0126 (12) | −0.0061 (11) |
C7 | 0.0511 (15) | 0.0449 (15) | 0.0485 (15) | 0.0035 (11) | 0.0077 (12) | −0.0019 (11) |
C8 | 0.0531 (16) | 0.0491 (15) | 0.0472 (15) | −0.0061 (12) | 0.0089 (12) | 0.0056 (11) |
C9 | 0.0595 (18) | 0.0673 (19) | 0.0581 (17) | −0.0024 (14) | 0.0237 (14) | −0.0017 (14) |
C10 | 0.0656 (18) | 0.0530 (17) | 0.0647 (17) | 0.0071 (14) | 0.0280 (14) | −0.0060 (13) |
C11 | 0.0507 (15) | 0.0433 (15) | 0.0482 (14) | −0.0012 (11) | 0.0085 (12) | −0.0032 (11) |
C12 | 0.0482 (15) | 0.0397 (14) | 0.0478 (14) | 0.0011 (11) | 0.0100 (12) | −0.0028 (11) |
Geometric parameters (Å, º) top
O1—C11 | 1.353 (3) | C5—H5B | 0.9700 |
O1—C3A | 1.430 (4) | C3A—C4A | 1.514 (9) |
O1—C3 | 1.431 (3) | C3A—H3AA | 0.9800 |
O2—C1 | 1.211 (3) | C4A—C5A | 1.537 (4) |
O3—N | 1.224 (3) | C4A—H4AA | 0.9700 |
O4—N | 1.222 (3) | C4A—H4AB | 0.9700 |
N—C8 | 1.462 (3) | C5A—H5AA | 0.9700 |
C1—C2 | 1.468 (3) | C5A—H5AB | 0.9700 |
C1—C5A | 1.510 (5) | C6—C12 | 1.449 (3) |
C1—C5 | 1.510 (5) | C6—H6A | 0.9300 |
C2—C6 | 1.320 (3) | C7—C8 | 1.382 (3) |
C2—C3 | 1.537 (4) | C7—C12 | 1.387 (3) |
C2—C3A | 1.539 (4) | C7—H7A | 0.9300 |
C3—C4 | 1.514 (9) | C8—C9 | 1.375 (3) |
C3—H3A | 0.9800 | C9—C10 | 1.376 (3) |
C4—C5 | 1.537 (4) | C9—H9A | 0.9300 |
C4—H4A | 0.9700 | C10—C11 | 1.377 (3) |
C4—H4B | 0.9700 | C10—H10A | 0.9300 |
C5—H5A | 0.9700 | C11—C12 | 1.405 (3) |
| | | |
C11—O1—C3A | 118.6 (4) | O1—C3A—H3AA | 109.6 |
C11—O1—C3 | 117.9 (2) | C4A—C3A—H3AA | 109.6 |
O4—N—O3 | 123.1 (2) | C2—C3A—H3AA | 109.6 |
O4—N—C8 | 118.4 (2) | C3A—C4A—C5A | 99.8 (17) |
O3—N—C8 | 118.5 (2) | C3A—C4A—H4AA | 111.8 |
O2—C1—C2 | 125.8 (2) | C5A—C4A—H4AA | 111.8 |
O2—C1—C5A | 129.7 (10) | C3A—C4A—H4AB | 111.8 |
C2—C1—C5A | 103.6 (10) | C5A—C4A—H4AB | 111.8 |
O2—C1—C5 | 125.1 (5) | H4AA—C4A—H4AB | 109.5 |
C2—C1—C5 | 109.0 (5) | C1—C5A—C4A | 111.3 (15) |
C6—C2—C1 | 131.2 (2) | C1—C5A—H5AA | 109.4 |
C6—C2—C3 | 120.9 (2) | C4A—C5A—H5AA | 109.4 |
C1—C2—C3 | 107.8 (2) | C1—C5A—H5AB | 109.4 |
C6—C2—C3A | 117.6 (5) | C4A—C5A—H5AB | 109.4 |
C1—C2—C3A | 103.9 (3) | H5AA—C5A—H5AB | 108.0 |
O1—C3—C4 | 112.7 (6) | C2—C6—C12 | 118.7 (2) |
O1—C3—C2 | 110.2 (2) | C2—C6—H6A | 120.6 |
C4—C3—C2 | 100.1 (5) | C12—C6—H6A | 120.6 |
O1—C3—H3A | 111.1 | C8—C7—C12 | 119.7 (2) |
C4—C3—H3A | 111.1 | C8—C7—H7A | 120.1 |
C2—C3—H3A | 111.1 | C12—C7—H7A | 120.1 |
C3—C4—C5 | 108.0 (7) | C9—C8—C7 | 121.4 (2) |
C3—C4—H4A | 110.1 | C9—C8—N | 119.5 (2) |
C5—C4—H4A | 110.1 | C7—C8—N | 119.2 (2) |
C3—C4—H4B | 110.1 | C8—C9—C10 | 119.5 (2) |
C5—C4—H4B | 110.1 | C8—C9—H9A | 120.3 |
H4A—C4—H4B | 108.4 | C10—C9—H9A | 120.3 |
C1—C5—C4 | 102.9 (7) | C9—C10—C11 | 120.1 (2) |
C1—C5—H5A | 111.2 | C9—C10—H10A | 120.0 |
C4—C5—H5A | 111.2 | C11—C10—H10A | 120.0 |
C1—C5—H5B | 111.2 | O1—C11—C10 | 117.2 (2) |
C4—C5—H5B | 111.2 | O1—C11—C12 | 122.0 (2) |
H5A—C5—H5B | 109.1 | C10—C11—C12 | 120.8 (2) |
O1—C3A—C4A | 111.9 (15) | C7—C12—C11 | 118.5 (2) |
O1—C3A—C2 | 110.2 (3) | C7—C12—C6 | 123.2 (2) |
C4A—C3A—C2 | 105.7 (13) | C11—C12—C6 | 118.3 (2) |
| | | |
O2—C1—C2—C6 | −9.8 (5) | C3—C2—C3A—C4A | 59.8 (19) |
C5A—C1—C2—C6 | 179.5 (18) | O1—C3A—C4A—C5A | 152 (2) |
C5—C1—C2—C6 | 167.6 (8) | C2—C3A—C4A—C5A | 32 (3) |
O2—C1—C2—C3 | 165.4 (3) | O2—C1—C5A—C4A | 178 (2) |
C5A—C1—C2—C3 | −5.3 (18) | C2—C1—C5A—C4A | −12 (3) |
C5—C1—C2—C3 | −17.3 (8) | C5—C1—C5A—C4A | 105 (8) |
O2—C1—C2—C3A | −158.2 (6) | C3A—C4A—C5A—C1 | −13 (4) |
C5A—C1—C2—C3A | 31.1 (19) | C1—C2—C6—C12 | −174.3 (2) |
C5—C1—C2—C3A | 19.2 (10) | C3—C2—C6—C12 | 11.1 (4) |
C11—O1—C3—C4 | 150.3 (6) | C3A—C2—C6—C12 | −29.3 (6) |
C3A—O1—C3—C4 | 48.7 (11) | C12—C7—C8—C9 | 2.3 (4) |
C11—O1—C3—C2 | 39.4 (5) | C12—C7—C8—N | −179.0 (2) |
C3A—O1—C3—C2 | −62.2 (4) | O4—N—C8—C9 | −177.1 (2) |
C6—C2—C3—O1 | −33.9 (5) | O3—N—C8—C9 | 2.2 (4) |
C1—C2—C3—O1 | 150.3 (3) | O4—N—C8—C7 | 4.2 (4) |
C3A—C2—C3—O1 | 61.3 (4) | O3—N—C8—C7 | −176.6 (2) |
C6—C2—C3—C4 | −152.8 (6) | C7—C8—C9—C10 | −1.3 (4) |
C1—C2—C3—C4 | 31.4 (7) | N—C8—C9—C10 | 179.9 (2) |
C3A—C2—C3—C4 | −57.7 (11) | C8—C9—C10—C11 | −1.1 (4) |
O1—C3—C4—C5 | −151.6 (8) | C3A—O1—C11—C10 | −159.4 (6) |
C2—C3—C4—C5 | −34.5 (11) | C3—O1—C11—C10 | 157.2 (3) |
O2—C1—C5—C4 | 172.9 (8) | C3A—O1—C11—C12 | 19.0 (7) |
C2—C1—C5—C4 | −4.5 (13) | C3—O1—C11—C12 | −24.4 (4) |
C5A—C1—C5—C4 | −71 (6) | C9—C10—C11—O1 | −179.1 (2) |
C3—C4—C5—C1 | 25.2 (14) | C9—C10—C11—C12 | 2.5 (4) |
C11—O1—C3A—C4A | −155.0 (16) | C8—C7—C12—C11 | −0.9 (3) |
C3—O1—C3A—C4A | −55.3 (19) | C8—C7—C12—C6 | −179.3 (2) |
C11—O1—C3A—C2 | −37.7 (12) | O1—C11—C12—C7 | −179.8 (2) |
C3—O1—C3A—C2 | 62.1 (4) | C10—C11—C12—C7 | −1.5 (4) |
C6—C2—C3A—O1 | 44.0 (11) | O1—C11—C12—C6 | −1.3 (3) |
C1—C2—C3A—O1 | −162.5 (8) | C10—C11—C12—C6 | 177.0 (2) |
C3—C2—C3A—O1 | −61.3 (4) | C2—C6—C12—C7 | −174.0 (2) |
C6—C2—C3A—C4A | 165.1 (17) | C2—C6—C12—C11 | 7.5 (3) |
C1—C2—C3A—C4A | −41.4 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O2i | 0.93 | 2.57 | 3.380 (3) | 146 |
C7—H7A···O2i | 0.93 | 2.56 | 3.390 (3) | 149 |
Symmetry code: (i) −x, −y+2, −z+2. |