In the crystal structure of the title compound, C
14H
12N
4O
5, molecules are connected
via weak intermolecular N—H
O and C—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 298471
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.096
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT707_ALERT_1_A D...A Calc 28.998(12), Rep 3.188(3), Dev.. 2150.83 Sigma
C14 -O2 1.555 4.664
PLAT726_ALERT_1_A H...A Calc 28.63000, Rep 2.56000 Dev... 26.07 Ang.
H14B -O2 1.555 4.664
PLAT728_ALERT_1_A D-H..A Calc 112.00, Rep 123.00 Dev... 11.00 Deg.
C14 -H14B -O2 1.555 1.555 4.664
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O4 .. O4 .. 2.76 Ang.
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N2 .. 5.51 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O4 .. 2.62 Ang.
PLAT737_ALERT_1_C D...A Calc 28.998(12), Rep 3.188(3) ...... 4.00 su-Rat
C14 -O2 1.555 4.664
3 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Crystal data top
C14H12N4O5 | F(000) = 656 |
Mr = 316.28 | Dx = 1.492 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.189 (2) Å | Cell parameters from 2340 reflections |
b = 8.581 (3) Å | θ = 3.1–26.1° |
c = 26.669 (11) Å | µ = 0.12 mm−1 |
β = 96.392 (5)° | T = 294 K |
V = 1407.5 (9) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.20 × 0.18 mm |
Data collection top
CCD area detector diffractometer | 2481 independent reflections |
Radiation source: fine-focus sealed tube | 1914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→6 |
Tmin = 0.963, Tmax = 0.979 | k = −10→9 |
7349 measured reflections | l = −31→31 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1714P] where P = (Fo2 + 2Fc2)/3 |
2481 reflections | (Δ/σ)max < 0.001 |
213 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.21 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 | |
O1 | 0.3423 (2) | 0.45260 (16) | 0.24373 (4) | 0.0786 (4) | |
O2 | 0.0374 (2) | 0.57267 (15) | 0.24395 (4) | 0.0732 (4) | |
O3 | −0.21341 (15) | 0.91196 (13) | 0.11194 (4) | 0.0544 (3) | |
O4 | −0.05330 (15) | 0.93642 (13) | 0.04464 (4) | 0.0485 (3) | |
O5 | 1.16761 (16) | 0.67880 (13) | −0.15044 (4) | 0.0534 (3) | |
N1 | 0.2021 (2) | 0.54176 (16) | 0.22460 (5) | 0.0554 (4) | |
N2 | −0.06467 (17) | 0.88067 (13) | 0.08692 (4) | 0.0396 (3) | |
N3 | 0.31318 (19) | 0.79195 (15) | 0.03573 (4) | 0.0410 (3) | |
H3 | 0.218 (3) | 0.856 (2) | 0.0209 (6) | 0.063 (5)* | |
N4 | 0.49046 (17) | 0.74551 (14) | 0.01246 (4) | 0.0407 (3) | |
C1 | 0.4396 (2) | 0.63427 (17) | 0.10686 (5) | 0.0438 (4) | |
H1 | 0.5617 | 0.6076 | 0.0914 | 0.053* | |
C2 | 0.4153 (2) | 0.57340 (18) | 0.15287 (6) | 0.0468 (4) | |
H2 | 0.5199 | 0.5063 | 0.1685 | 0.056* | |
C3 | 0.2329 (2) | 0.61192 (16) | 0.17645 (5) | 0.0430 (3) | |
C4 | 0.0793 (2) | 0.71209 (16) | 0.15458 (5) | 0.0413 (3) | |
H4 | −0.0409 | 0.7378 | 0.1709 | 0.050* | |
C5 | 0.1041 (2) | 0.77512 (15) | 0.10779 (5) | 0.0361 (3) | |
C6 | 0.2851 (2) | 0.73685 (15) | 0.08180 (5) | 0.0369 (3) | |
C7 | 0.4991 (2) | 0.80444 (17) | −0.03114 (5) | 0.0392 (3) | |
H7 | 0.3898 | 0.8727 | −0.0439 | 0.047* | |
C8 | 0.6728 (2) | 0.76941 (16) | −0.06176 (5) | 0.0366 (3) | |
C9 | 0.8453 (2) | 0.66906 (16) | −0.04617 (5) | 0.0394 (3) | |
H9 | 0.8509 | 0.6203 | −0.0149 | 0.047* | |
C10 | 1.0061 (2) | 0.64189 (17) | −0.07647 (5) | 0.0407 (3) | |
H10 | 1.1199 | 0.5748 | −0.0657 | 0.049* | |
C11 | 1.0002 (2) | 0.71415 (16) | −0.12336 (5) | 0.0394 (3) | |
C12 | 0.8303 (2) | 0.81308 (17) | −0.13959 (5) | 0.0405 (3) | |
H12 | 0.8245 | 0.8612 | −0.1710 | 0.049* | |
C13 | 0.6694 (2) | 0.83953 (17) | −0.10867 (5) | 0.0398 (3) | |
H13 | 0.5554 | 0.9063 | −0.1196 | 0.048* | |
C14 | 1.1818 (3) | 0.7624 (2) | −0.19634 (6) | 0.0601 (5) | |
H14A | 1.0598 | 0.7361 | −0.2203 | 0.090* | |
H14B | 1.3141 | 0.7347 | −0.2098 | 0.090* | |
H14C | 1.1811 | 0.8723 | −0.1897 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0997 (10) | 0.0805 (9) | 0.0560 (7) | 0.0226 (8) | 0.0102 (7) | 0.0210 (7) |
O2 | 0.0946 (9) | 0.0761 (9) | 0.0554 (7) | 0.0086 (7) | 0.0364 (7) | 0.0042 (6) |
O3 | 0.0427 (6) | 0.0635 (7) | 0.0608 (7) | 0.0119 (5) | 0.0231 (5) | 0.0002 (5) |
O4 | 0.0453 (6) | 0.0573 (7) | 0.0442 (6) | 0.0096 (5) | 0.0103 (5) | 0.0060 (5) |
O5 | 0.0477 (6) | 0.0642 (7) | 0.0528 (6) | 0.0114 (5) | 0.0257 (5) | 0.0062 (5) |
N1 | 0.0774 (10) | 0.0484 (8) | 0.0416 (7) | −0.0004 (7) | 0.0121 (7) | −0.0024 (6) |
N2 | 0.0341 (6) | 0.0406 (7) | 0.0454 (7) | 0.0001 (5) | 0.0098 (5) | −0.0048 (5) |
N3 | 0.0343 (6) | 0.0494 (8) | 0.0413 (7) | 0.0062 (5) | 0.0128 (5) | 0.0004 (6) |
N4 | 0.0339 (6) | 0.0468 (7) | 0.0435 (7) | 0.0018 (5) | 0.0133 (5) | −0.0047 (5) |
C1 | 0.0384 (7) | 0.0446 (8) | 0.0503 (9) | 0.0047 (6) | 0.0124 (6) | −0.0024 (7) |
C2 | 0.0481 (8) | 0.0431 (9) | 0.0494 (9) | 0.0051 (6) | 0.0055 (7) | 0.0009 (7) |
C3 | 0.0540 (9) | 0.0389 (8) | 0.0366 (7) | −0.0022 (7) | 0.0081 (6) | −0.0023 (6) |
C4 | 0.0450 (8) | 0.0379 (8) | 0.0430 (8) | −0.0030 (6) | 0.0142 (6) | −0.0090 (6) |
C5 | 0.0345 (7) | 0.0360 (8) | 0.0389 (7) | −0.0009 (5) | 0.0088 (6) | −0.0056 (6) |
C6 | 0.0346 (7) | 0.0355 (7) | 0.0415 (8) | −0.0035 (6) | 0.0080 (6) | −0.0057 (6) |
C7 | 0.0342 (7) | 0.0437 (8) | 0.0405 (8) | 0.0021 (6) | 0.0071 (6) | −0.0024 (6) |
C8 | 0.0332 (7) | 0.0385 (8) | 0.0389 (7) | −0.0019 (6) | 0.0073 (6) | −0.0048 (6) |
C9 | 0.0396 (7) | 0.0437 (8) | 0.0354 (7) | 0.0006 (6) | 0.0067 (6) | 0.0015 (6) |
C10 | 0.0358 (7) | 0.0429 (8) | 0.0439 (8) | 0.0053 (6) | 0.0058 (6) | 0.0001 (6) |
C11 | 0.0356 (7) | 0.0415 (8) | 0.0430 (8) | −0.0015 (6) | 0.0125 (6) | −0.0058 (6) |
C12 | 0.0422 (8) | 0.0452 (8) | 0.0347 (7) | −0.0003 (6) | 0.0067 (6) | 0.0009 (6) |
C13 | 0.0357 (7) | 0.0429 (8) | 0.0407 (8) | 0.0049 (6) | 0.0031 (6) | −0.0018 (6) |
C14 | 0.0614 (10) | 0.0671 (11) | 0.0573 (10) | 0.0039 (8) | 0.0313 (8) | 0.0054 (9) |
Geometric parameters (Å, º) top
O1—N1 | 1.2252 (18) | C4—C5 | 1.3841 (19) |
O2—N1 | 1.2217 (17) | C4—H4 | 0.9300 |
O3—N2 | 1.2254 (14) | C5—C6 | 1.4199 (18) |
O4—N2 | 1.2339 (15) | C7—C8 | 1.4516 (18) |
O5—C11 | 1.3614 (15) | C7—H7 | 0.9300 |
O5—C14 | 1.4298 (18) | C8—C13 | 1.3864 (19) |
N1—C3 | 1.4500 (19) | C8—C9 | 1.3984 (19) |
N2—C5 | 1.4462 (18) | C9—C10 | 1.3703 (18) |
N3—C6 | 1.3457 (18) | C9—H9 | 0.9300 |
N3—N4 | 1.3782 (15) | C10—C11 | 1.393 (2) |
N3—H3 | 0.869 (18) | C10—H10 | 0.9300 |
N4—C7 | 1.2746 (18) | C11—C12 | 1.383 (2) |
C1—C2 | 1.357 (2) | C12—C13 | 1.3809 (18) |
C1—C6 | 1.412 (2) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.392 (2) | C14—H14A | 0.9600 |
C2—H2 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.364 (2) | C14—H14C | 0.9600 |
| | | |
C11—O5—C14 | 117.74 (11) | C1—C6—C5 | 116.28 (13) |
O2—N1—O1 | 123.06 (14) | N4—C7—C8 | 122.69 (13) |
O2—N1—C3 | 118.84 (14) | N4—C7—H7 | 118.7 |
O1—N1—C3 | 118.09 (13) | C8—C7—H7 | 118.7 |
O3—N2—O4 | 122.36 (12) | C13—C8—C9 | 118.03 (12) |
O3—N2—C5 | 118.80 (12) | C13—C8—C7 | 118.68 (12) |
O4—N2—C5 | 118.84 (10) | C9—C8—C7 | 123.29 (12) |
C6—N3—N4 | 119.99 (12) | C10—C9—C8 | 120.69 (13) |
C6—N3—H3 | 119.3 (10) | C10—C9—H9 | 119.7 |
N4—N3—H3 | 120.7 (11) | C8—C9—H9 | 119.7 |
C7—N4—N3 | 114.37 (12) | C9—C10—C11 | 120.37 (13) |
C2—C1—C6 | 122.04 (13) | C9—C10—H10 | 119.8 |
C2—C1—H1 | 119.0 | C11—C10—H10 | 119.8 |
C6—C1—H1 | 119.0 | O5—C11—C12 | 124.60 (13) |
C1—C2—C3 | 119.62 (14) | O5—C11—C10 | 115.57 (12) |
C1—C2—H2 | 120.2 | C12—C11—C10 | 119.83 (12) |
C3—C2—H2 | 120.2 | C13—C12—C11 | 119.21 (13) |
C4—C3—C2 | 121.22 (13) | C13—C12—H12 | 120.4 |
C4—C3—N1 | 119.09 (13) | C11—C12—H12 | 120.4 |
C2—C3—N1 | 119.67 (14) | C12—C13—C8 | 121.87 (13) |
C3—C4—C5 | 119.35 (12) | C12—C13—H13 | 119.1 |
C3—C4—H4 | 120.3 | C8—C13—H13 | 119.1 |
C5—C4—H4 | 120.3 | O5—C14—H14A | 109.5 |
C4—C5—C6 | 121.48 (13) | O5—C14—H14B | 109.5 |
C4—C5—N2 | 116.37 (11) | H14A—C14—H14B | 109.5 |
C6—C5—N2 | 122.15 (12) | O5—C14—H14C | 109.5 |
N3—C6—C1 | 120.10 (12) | H14A—C14—H14C | 109.5 |
N3—C6—C5 | 123.62 (13) | H14B—C14—H14C | 109.5 |
| | | |
C6—N3—N4—C7 | 179.55 (12) | C4—C5—C6—N3 | 178.22 (12) |
C6—C1—C2—C3 | 0.2 (2) | N2—C5—C6—N3 | −1.4 (2) |
C1—C2—C3—C4 | −1.1 (2) | C4—C5—C6—C1 | −1.4 (2) |
C1—C2—C3—N1 | 177.35 (13) | N2—C5—C6—C1 | 179.02 (12) |
O2—N1—C3—C4 | 1.0 (2) | N3—N4—C7—C8 | −179.74 (12) |
O1—N1—C3—C4 | −179.69 (14) | N4—C7—C8—C13 | −179.72 (13) |
O2—N1—C3—C2 | −177.49 (14) | N4—C7—C8—C9 | −0.3 (2) |
O1—N1—C3—C2 | 1.8 (2) | C13—C8—C9—C10 | 0.3 (2) |
C2—C3—C4—C5 | 0.8 (2) | C7—C8—C9—C10 | −179.18 (13) |
N1—C3—C4—C5 | −177.72 (12) | C8—C9—C10—C11 | 0.0 (2) |
C3—C4—C5—C6 | 0.5 (2) | C14—O5—C11—C12 | 7.1 (2) |
C3—C4—C5—N2 | −179.86 (12) | C14—O5—C11—C10 | −173.46 (13) |
O3—N2—C5—C4 | 2.33 (18) | C9—C10—C11—O5 | −179.86 (12) |
O4—N2—C5—C4 | −177.93 (12) | C9—C10—C11—C12 | −0.4 (2) |
O3—N2—C5—C6 | −178.05 (12) | O5—C11—C12—C13 | 179.85 (13) |
O4—N2—C5—C6 | 1.69 (19) | C10—C11—C12—C13 | 0.5 (2) |
N4—N3—C6—C1 | 1.4 (2) | C11—C12—C13—C8 | −0.1 (2) |
N4—N3—C6—C5 | −178.13 (12) | C9—C8—C13—C12 | −0.2 (2) |
C2—C1—C6—N3 | −178.59 (14) | C7—C8—C13—C12 | 179.25 (13) |
C2—C1—C6—C5 | 1.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4 | 0.869 (18) | 1.984 (17) | 2.6189 (17) | 129.0 (14) |
N3—H3···O4i | 0.869 (18) | 2.620 (18) | 3.4419 (19) | 158.2 (14) |
C2—H2···O5ii | 0.93 | 2.59 | 3.375 (2) | 143 |
C14—H14B···O2iii | 0.96 | 2.56 | 3.188 (3) | 123 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+2, −y+1, −z; (iii) x+1/2, −y+1/2, z−3/2. |