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In the crystal structure of the title compound, C12H9NO4, the disordered pyran ring adopts a half-chair conformation. Weak intermolecular C—H...O hydrogen bonds link mol­ecules into centrosymmetric dimers, which generate R_2^1(6), R_2^2(10) and R_2^2(14) rings. In addition, π–π stacking interactions are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026078/lh6267sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026078/lh6267Isup2.hkl
Contains datablock I

CCDC reference: 255924

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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-1H-cyclopenta[b]chromen-1-one top
Crystal data top
C12H9NO4F(000) = 480
Mr = 231.20Dx = 1.451 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6400 reflections
a = 6.0584 (11) Åθ = 2.5–22.4°
b = 19.717 (4) ŵ = 0.11 mm1
c = 8.9513 (16) ÅT = 293 K
β = 98.257 (4)°Block, yellow
V = 1058.2 (3) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1850 independent reflections
Radiation source: fine-focus sealed tube1165 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 76
Tmin = 0.978, Tmax = 0.989k = 2320
4356 measured reflectionsl = 109
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-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 reflectionsΔρmax = 0.17 e Å3
183 parametersΔρmin = 0.18 e Å3
5 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
O10.4651 (3)0.83740 (8)0.77807 (19)0.0625 (6)
O20.1177 (3)0.88831 (9)1.0617 (2)0.0688 (6)
O30.8800 (4)1.10283 (10)0.5657 (2)0.0920 (7)
O40.6501 (3)1.14603 (9)0.7013 (2)0.0784 (6)
N0.7345 (4)1.09737 (11)0.6467 (2)0.0636 (6)
C10.0167 (4)0.85576 (13)1.0037 (3)0.0542 (7)
C20.1961 (4)0.88384 (12)0.9283 (3)0.0563 (7)
C30.3602 (8)0.82608 (17)0.9093 (5)0.0518 (14)0.720 (9)
H3A0.47130.82120.99970.078*0.720 (9)
C40.201 (2)0.7664 (3)0.8916 (16)0.081 (4)0.720 (9)
H4A0.28070.72490.92240.121*0.720 (9)
H4B0.13470.76180.78690.121*0.720 (9)
C50.019 (3)0.7794 (2)0.9913 (18)0.072 (4)0.720 (9)
H5A0.12420.76230.94400.109*0.720 (9)
H5B0.05680.75841.08970.109*0.720 (9)
C3A0.2518 (12)0.8261 (5)0.8243 (15)0.063 (4)0.280 (9)
H3AA0.13730.82370.73530.094*0.280 (9)
C4A0.248 (6)0.7617 (10)0.916 (4)0.078 (9)0.280 (9)
H4AA0.39060.75300.97720.118*0.280 (9)
H4AB0.20440.72270.85270.118*0.280 (9)
C5A0.068 (6)0.7808 (3)1.013 (4)0.054 (6)0.280 (9)
H5AA0.06710.75530.97980.081*0.280 (9)
H5AB0.11880.76861.11770.081*0.280 (9)
C60.2374 (4)0.94652 (12)0.8885 (3)0.0467 (6)
H6A0.15220.98250.91570.056*
C70.4879 (4)1.02246 (12)0.7660 (3)0.0481 (6)
H7A0.41901.06070.79900.058*
C80.6601 (4)1.02938 (12)0.6814 (3)0.0496 (6)
C90.7598 (4)0.97373 (13)0.6268 (3)0.0602 (7)
H9A0.87350.97930.56830.072*
C100.6900 (4)0.90974 (13)0.6596 (3)0.0593 (7)
H10A0.75490.87190.62170.071*
C110.5241 (4)0.90166 (12)0.7483 (3)0.0473 (6)
C120.4181 (4)0.95823 (11)0.8018 (2)0.0449 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0739 (13)0.0435 (11)0.0768 (13)0.0021 (9)0.0342 (10)0.0077 (8)
O20.0674 (12)0.0591 (12)0.0879 (13)0.0027 (10)0.0380 (11)0.0003 (10)
O30.1031 (17)0.0844 (16)0.1007 (16)0.0194 (12)0.0565 (14)0.0038 (12)
O40.0886 (15)0.0490 (12)0.1032 (15)0.0041 (11)0.0325 (12)0.0105 (11)
N0.0667 (16)0.0626 (16)0.0631 (15)0.0032 (12)0.0148 (13)0.0079 (12)
C10.0528 (16)0.0506 (16)0.0615 (16)0.0038 (13)0.0161 (14)0.0035 (13)
C20.0599 (17)0.0403 (15)0.0733 (17)0.0028 (12)0.0255 (14)0.0064 (13)
C30.053 (3)0.041 (2)0.065 (3)0.0046 (19)0.018 (2)0.005 (2)
C40.092 (7)0.026 (4)0.135 (9)0.001 (3)0.054 (7)0.009 (4)
C50.073 (7)0.052 (4)0.098 (8)0.004 (3)0.034 (6)0.013 (4)
C3A0.051 (7)0.056 (7)0.081 (9)0.007 (6)0.010 (6)0.005 (6)
C4A0.072 (12)0.087 (18)0.082 (11)0.012 (10)0.032 (9)0.033 (10)
C5A0.055 (13)0.040 (9)0.070 (9)0.024 (6)0.013 (9)0.008 (8)
C60.0483 (15)0.0405 (14)0.0530 (14)0.0067 (11)0.0126 (12)0.0061 (11)
C70.0511 (15)0.0449 (15)0.0485 (15)0.0035 (11)0.0077 (12)0.0019 (11)
C80.0531 (16)0.0491 (15)0.0472 (15)0.0061 (12)0.0089 (12)0.0056 (11)
C90.0595 (18)0.0673 (19)0.0581 (17)0.0024 (14)0.0237 (14)0.0017 (14)
C100.0656 (18)0.0530 (17)0.0647 (17)0.0071 (14)0.0280 (14)0.0060 (13)
C110.0507 (15)0.0433 (15)0.0482 (14)0.0012 (11)0.0085 (12)0.0032 (11)
C120.0482 (15)0.0397 (14)0.0478 (14)0.0011 (11)0.0100 (12)0.0028 (11)
Geometric parameters (Å, º) top
O1—C111.353 (3)C5—H5B0.9700
O1—C3A1.430 (4)C3A—C4A1.514 (9)
O1—C31.431 (3)C3A—H3AA0.9800
O2—C11.211 (3)C4A—C5A1.537 (4)
O3—N1.224 (3)C4A—H4AA0.9700
O4—N1.222 (3)C4A—H4AB0.9700
N—C81.462 (3)C5A—H5AA0.9700
C1—C21.468 (3)C5A—H5AB0.9700
C1—C5A1.510 (5)C6—C121.449 (3)
C1—C51.510 (5)C6—H6A0.9300
C2—C61.320 (3)C7—C81.382 (3)
C2—C31.537 (4)C7—C121.387 (3)
C2—C3A1.539 (4)C7—H7A0.9300
C3—C41.514 (9)C8—C91.375 (3)
C3—H3A0.9800C9—C101.376 (3)
C4—C51.537 (4)C9—H9A0.9300
C4—H4A0.9700C10—C111.377 (3)
C4—H4B0.9700C10—H10A0.9300
C5—H5A0.9700C11—C121.405 (3)
C11—O1—C3A118.6 (4)O1—C3A—H3AA109.6
C11—O1—C3117.9 (2)C4A—C3A—H3AA109.6
O4—N—O3123.1 (2)C2—C3A—H3AA109.6
O4—N—C8118.4 (2)C3A—C4A—C5A99.8 (17)
O3—N—C8118.5 (2)C3A—C4A—H4AA111.8
O2—C1—C2125.8 (2)C5A—C4A—H4AA111.8
O2—C1—C5A129.7 (10)C3A—C4A—H4AB111.8
C2—C1—C5A103.6 (10)C5A—C4A—H4AB111.8
O2—C1—C5125.1 (5)H4AA—C4A—H4AB109.5
C2—C1—C5109.0 (5)C1—C5A—C4A111.3 (15)
C6—C2—C1131.2 (2)C1—C5A—H5AA109.4
C6—C2—C3120.9 (2)C4A—C5A—H5AA109.4
C1—C2—C3107.8 (2)C1—C5A—H5AB109.4
C6—C2—C3A117.6 (5)C4A—C5A—H5AB109.4
C1—C2—C3A103.9 (3)H5AA—C5A—H5AB108.0
O1—C3—C4112.7 (6)C2—C6—C12118.7 (2)
O1—C3—C2110.2 (2)C2—C6—H6A120.6
C4—C3—C2100.1 (5)C12—C6—H6A120.6
O1—C3—H3A111.1C8—C7—C12119.7 (2)
C4—C3—H3A111.1C8—C7—H7A120.1
C2—C3—H3A111.1C12—C7—H7A120.1
C3—C4—C5108.0 (7)C9—C8—C7121.4 (2)
C3—C4—H4A110.1C9—C8—N119.5 (2)
C5—C4—H4A110.1C7—C8—N119.2 (2)
C3—C4—H4B110.1C8—C9—C10119.5 (2)
C5—C4—H4B110.1C8—C9—H9A120.3
H4A—C4—H4B108.4C10—C9—H9A120.3
C1—C5—C4102.9 (7)C9—C10—C11120.1 (2)
C1—C5—H5A111.2C9—C10—H10A120.0
C4—C5—H5A111.2C11—C10—H10A120.0
C1—C5—H5B111.2O1—C11—C10117.2 (2)
C4—C5—H5B111.2O1—C11—C12122.0 (2)
H5A—C5—H5B109.1C10—C11—C12120.8 (2)
O1—C3A—C4A111.9 (15)C7—C12—C11118.5 (2)
O1—C3A—C2110.2 (3)C7—C12—C6123.2 (2)
C4A—C3A—C2105.7 (13)C11—C12—C6118.3 (2)
O2—C1—C2—C69.8 (5)C3—C2—C3A—C4A59.8 (19)
C5A—C1—C2—C6179.5 (18)O1—C3A—C4A—C5A152 (2)
C5—C1—C2—C6167.6 (8)C2—C3A—C4A—C5A32 (3)
O2—C1—C2—C3165.4 (3)O2—C1—C5A—C4A178 (2)
C5A—C1—C2—C35.3 (18)C2—C1—C5A—C4A12 (3)
C5—C1—C2—C317.3 (8)C5—C1—C5A—C4A105 (8)
O2—C1—C2—C3A158.2 (6)C3A—C4A—C5A—C113 (4)
C5A—C1—C2—C3A31.1 (19)C1—C2—C6—C12174.3 (2)
C5—C1—C2—C3A19.2 (10)C3—C2—C6—C1211.1 (4)
C11—O1—C3—C4150.3 (6)C3A—C2—C6—C1229.3 (6)
C3A—O1—C3—C448.7 (11)C12—C7—C8—C92.3 (4)
C11—O1—C3—C239.4 (5)C12—C7—C8—N179.0 (2)
C3A—O1—C3—C262.2 (4)O4—N—C8—C9177.1 (2)
C6—C2—C3—O133.9 (5)O3—N—C8—C92.2 (4)
C1—C2—C3—O1150.3 (3)O4—N—C8—C74.2 (4)
C3A—C2—C3—O161.3 (4)O3—N—C8—C7176.6 (2)
C6—C2—C3—C4152.8 (6)C7—C8—C9—C101.3 (4)
C1—C2—C3—C431.4 (7)N—C8—C9—C10179.9 (2)
C3A—C2—C3—C457.7 (11)C8—C9—C10—C111.1 (4)
O1—C3—C4—C5151.6 (8)C3A—O1—C11—C10159.4 (6)
C2—C3—C4—C534.5 (11)C3—O1—C11—C10157.2 (3)
O2—C1—C5—C4172.9 (8)C3A—O1—C11—C1219.0 (7)
C2—C1—C5—C44.5 (13)C3—O1—C11—C1224.4 (4)
C5A—C1—C5—C471 (6)C9—C10—C11—O1179.1 (2)
C3—C4—C5—C125.2 (14)C9—C10—C11—C122.5 (4)
C11—O1—C3A—C4A155.0 (16)C8—C7—C12—C110.9 (3)
C3—O1—C3A—C4A55.3 (19)C8—C7—C12—C6179.3 (2)
C11—O1—C3A—C237.7 (12)O1—C11—C12—C7179.8 (2)
C3—O1—C3A—C262.1 (4)C10—C11—C12—C71.5 (4)
C6—C2—C3A—O144.0 (11)O1—C11—C12—C61.3 (3)
C1—C2—C3A—O1162.5 (8)C10—C11—C12—C6177.0 (2)
C3—C2—C3A—O161.3 (4)C2—C6—C12—C7174.0 (2)
C6—C2—C3A—C4A165.1 (17)C2—C6—C12—C117.5 (3)
C1—C2—C3A—C4A41.4 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O2i0.932.573.380 (3)146
C7—H7A···O2i0.932.563.390 (3)149
Symmetry code: (i) x, y+2, z+2.
 

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