Buy article online - an online subscription or single-article purchase is required to access this article.
In the title sydnone compound, C
17H
12N
2O
3, the two benzene rings are oriented at angles of 7.37 (7) and 15.27 (7)° with respect to the plane of the sydnone moiety. In the crystalline state, the molecules are linked
via weak intermolecular C—H
O interactions, forming
C(4) and
C(7) chains, and
(14) and
(7) rings.
Supporting information
CCDC reference: 226998
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.065
- wR factor = 0.207
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 = 7.45 su
Alert level C
CRYSC01_ALERT_1_C There is an ordering error in _exptl_crystal_colour.
It should be (QUALIFIER) (INTENSITY) (BASE_COLOUR).
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30
0 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
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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: IPDS (Stoe & Cie, 1997); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
3-[4-(1-Oxo-3-phenylprop-2-en-1-yl)phenyl]sydnone
top
Crystal data top
C17H12N2O3 | F(000) = 608 |
Mr = 292.29 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Melting point: 471 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5839 (8) Å | Cell parameters from 6020 reflections |
b = 7.9343 (7) Å | θ = 1.9–28.0° |
c = 23.543 (2) Å | µ = 0.10 mm−1 |
β = 92.954 (8)° | T = 293 K |
V = 1414.8 (2) Å3 | Parallelepiped, translucent orange |
Z = 4 | 0.65 × 0.26 × 0.20 mm |
Data collection top
Stoe IPDS diffractometer | 2947 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Plane graphite monochromator | θmax = 29.5°, θmin = 2.7° |
rotation method scans | h = −10→10 |
13010 measured reflections | k = −10→10 |
3882 independent reflections | l = −32→32 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1085P)2 + 0.2927P] where P = (Fo2 + 2Fc2)/3 |
3882 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.26 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 | 1.0899 (2) | −0.28223 (17) | 0.12160 (5) | 0.0710 (4) | |
O5 | 1.1013 (3) | −0.3692 (2) | 0.21334 (7) | 0.0920 (5) | |
O12 | 0.6501 (3) | 0.6845 (2) | 0.07862 (8) | 0.1030 (6) | |
N2 | 1.0321 (2) | −0.1456 (2) | 0.09022 (6) | 0.0663 (4) | |
N3 | 0.96458 (18) | −0.04592 (18) | 0.12767 (5) | 0.0532 (3) | |
C4 | 0.9747 (3) | −0.1044 (2) | 0.18094 (7) | 0.0635 (5) | |
H4 | 0.9343 | −0.0507 | 0.2129 | 0.076* | |
C5 | 1.0569 (3) | −0.2603 (2) | 0.17958 (7) | 0.0669 (5) | |
C6 | 0.8936 (2) | 0.1122 (2) | 0.10736 (7) | 0.0526 (4) | |
C7 | 0.8591 (3) | 0.1319 (3) | 0.04943 (7) | 0.0637 (4) | |
H7 | 0.8762 | 0.0429 | 0.0246 | 0.076* | |
C8 | 0.7994 (3) | 0.2846 (3) | 0.02917 (8) | 0.0665 (5) | |
H8 | 0.7788 | 0.2998 | −0.0098 | 0.080* | |
C9 | 0.7695 (2) | 0.4169 (2) | 0.06597 (8) | 0.0610 (4) | |
C10 | 0.7979 (3) | 0.3902 (3) | 0.12435 (9) | 0.0676 (5) | |
H10 | 0.7735 | 0.4765 | 0.1495 | 0.081* | |
C11 | 0.8612 (3) | 0.2387 (3) | 0.14551 (8) | 0.0639 (4) | |
H11 | 0.8815 | 0.2224 | 0.1844 | 0.077* | |
C12 | 0.7033 (3) | 0.5842 (3) | 0.04496 (10) | 0.0703 (5) | |
C13 | 0.7037 (3) | 0.6208 (3) | −0.01619 (10) | 0.0734 (5) | |
H13 | 0.7488 | 0.5400 | −0.0401 | 0.088* | |
C14 | 0.6428 (3) | 0.7635 (3) | −0.03895 (10) | 0.0706 (5) | |
H14 | 0.6031 | 0.8421 | −0.0133 | 0.085* | |
C15 | 0.6292 (2) | 0.8152 (3) | −0.09884 (9) | 0.0639 (4) | |
C16 | 0.6753 (3) | 0.7086 (3) | −0.14187 (10) | 0.0748 (5) | |
H16 | 0.7176 | 0.6013 | −0.1329 | 0.090* | |
C17 | 0.6597 (3) | 0.7578 (4) | −0.19761 (12) | 0.0902 (7) | |
H17 | 0.6911 | 0.6837 | −0.2260 | 0.108* | |
C18 | 0.5979 (4) | 0.9164 (4) | −0.21212 (12) | 0.0979 (8) | |
H18 | 0.5879 | 0.9497 | −0.2500 | 0.117* | |
C19 | 0.5512 (3) | 1.0249 (3) | −0.16961 (13) | 0.0891 (7) | |
H19 | 0.5095 | 1.1321 | −0.1789 | 0.107* | |
C20 | 0.5661 (3) | 0.9754 (3) | −0.11373 (11) | 0.0747 (5) | |
H20 | 0.5337 | 1.0493 | −0.0854 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1054 (10) | 0.0560 (7) | 0.0524 (7) | 0.0090 (7) | 0.0119 (6) | 0.0002 (5) |
O5 | 0.1522 (16) | 0.0670 (9) | 0.0569 (8) | 0.0109 (9) | 0.0073 (8) | 0.0112 (7) |
O12 | 0.1371 (16) | 0.0823 (11) | 0.0887 (12) | 0.0340 (11) | −0.0019 (10) | −0.0103 (9) |
N2 | 0.0957 (11) | 0.0580 (8) | 0.0460 (7) | 0.0101 (8) | 0.0114 (7) | −0.0013 (6) |
N3 | 0.0623 (7) | 0.0552 (7) | 0.0423 (6) | −0.0028 (6) | 0.0068 (5) | −0.0037 (5) |
C4 | 0.0877 (12) | 0.0617 (10) | 0.0418 (7) | −0.0022 (8) | 0.0104 (7) | −0.0018 (7) |
C5 | 0.0963 (13) | 0.0581 (10) | 0.0466 (8) | −0.0061 (9) | 0.0061 (8) | 0.0005 (7) |
C6 | 0.0533 (8) | 0.0557 (9) | 0.0489 (8) | −0.0022 (6) | 0.0041 (6) | −0.0017 (6) |
C7 | 0.0766 (11) | 0.0660 (10) | 0.0490 (8) | 0.0088 (8) | 0.0065 (7) | −0.0059 (7) |
C8 | 0.0759 (11) | 0.0707 (12) | 0.0529 (9) | 0.0105 (9) | 0.0030 (8) | 0.0005 (8) |
C9 | 0.0547 (9) | 0.0607 (10) | 0.0672 (10) | 0.0003 (7) | −0.0022 (7) | −0.0021 (8) |
C10 | 0.0775 (11) | 0.0591 (10) | 0.0654 (10) | 0.0026 (8) | −0.0033 (8) | −0.0145 (8) |
C11 | 0.0773 (11) | 0.0635 (10) | 0.0504 (8) | 0.0003 (8) | −0.0012 (7) | −0.0089 (7) |
C12 | 0.0687 (11) | 0.0608 (10) | 0.0803 (13) | 0.0071 (8) | −0.0056 (9) | −0.0103 (9) |
C13 | 0.0706 (11) | 0.0627 (11) | 0.0861 (14) | 0.0099 (9) | −0.0031 (9) | −0.0030 (10) |
C14 | 0.0640 (10) | 0.0610 (10) | 0.0863 (13) | 0.0028 (8) | −0.0022 (9) | −0.0087 (9) |
C15 | 0.0525 (8) | 0.0622 (10) | 0.0768 (12) | −0.0043 (7) | 0.0024 (7) | −0.0035 (9) |
C16 | 0.0714 (11) | 0.0664 (12) | 0.0867 (14) | 0.0072 (9) | 0.0040 (10) | −0.0025 (10) |
C17 | 0.0927 (16) | 0.0940 (17) | 0.0852 (15) | 0.0093 (13) | 0.0179 (12) | −0.0113 (13) |
C18 | 0.1018 (18) | 0.107 (2) | 0.0853 (16) | 0.0041 (15) | 0.0124 (13) | 0.0178 (15) |
C19 | 0.0863 (15) | 0.0722 (14) | 0.1088 (19) | 0.0076 (11) | 0.0058 (13) | 0.0163 (13) |
C20 | 0.0707 (11) | 0.0624 (11) | 0.0911 (14) | 0.0011 (9) | 0.0053 (10) | −0.0060 (10) |
Geometric parameters (Å, º) top
O1—N2 | 1.371 (2) | C10—H10 | 0.93 |
O1—C5 | 1.411 (2) | C11—H11 | 0.93 |
O5—C5 | 1.210 (2) | C12—C13 | 1.469 (3) |
O12—C12 | 1.207 (3) | C13—C14 | 1.325 (3) |
N2—N3 | 1.308 (2) | C13—H13 | 0.93 |
N3—C4 | 1.336 (2) | C14—C15 | 1.467 (3) |
N3—C6 | 1.437 (2) | C14—H14 | 0.93 |
C4—C5 | 1.386 (3) | C15—C16 | 1.379 (3) |
C4—H4 | 0.93 | C15—C20 | 1.396 (3) |
C6—C11 | 1.378 (2) | C16—C17 | 1.368 (4) |
C6—C7 | 1.384 (2) | C16—H16 | 0.93 |
C7—C8 | 1.371 (3) | C17—C18 | 1.380 (4) |
C7—H7 | 0.93 | C17—H17 | 0.93 |
C8—C9 | 1.387 (3) | C18—C19 | 1.380 (4) |
C8—H8 | 0.93 | C18—H18 | 0.93 |
C9—C10 | 1.396 (3) | C19—C20 | 1.372 (4) |
C9—C12 | 1.495 (3) | C19—H19 | 0.93 |
C10—C11 | 1.378 (3) | C20—H20 | 0.93 |
| | | |
N2—O1—C5 | 110.85 (14) | C10—C11—H11 | 121.0 |
N3—N2—O1 | 103.91 (13) | O12—C12—C13 | 122.1 (2) |
N2—N3—C4 | 114.66 (15) | O12—C12—C9 | 119.1 (2) |
N2—N3—C6 | 117.16 (13) | C13—C12—C9 | 118.84 (18) |
C4—N3—C6 | 128.16 (14) | C14—C13—C12 | 123.1 (2) |
N3—C4—C5 | 107.00 (15) | C14—C13—H13 | 118.4 |
N3—C4—H4 | 126.5 | C12—C13—H13 | 118.4 |
C5—C4—H4 | 126.5 | C13—C14—C15 | 129.3 (2) |
O5—C5—C4 | 137.07 (18) | C13—C14—H14 | 115.3 |
O5—C5—O1 | 119.35 (18) | C15—C14—H14 | 115.3 |
C4—C5—O1 | 103.58 (15) | C16—C15—C20 | 118.1 (2) |
C11—C6—C7 | 121.92 (17) | C16—C15—C14 | 121.76 (19) |
C11—C6—N3 | 119.71 (15) | C20—C15—C14 | 120.15 (19) |
C7—C6—N3 | 118.37 (15) | C17—C16—C15 | 121.1 (2) |
C8—C7—C6 | 119.04 (17) | C17—C16—H16 | 119.4 |
C8—C7—H7 | 120.5 | C15—C16—H16 | 119.4 |
C6—C7—H7 | 120.5 | C16—C17—C18 | 120.6 (2) |
C7—C8—C9 | 120.87 (17) | C16—C17—H17 | 119.7 |
C7—C8—H8 | 119.6 | C18—C17—H17 | 119.7 |
C9—C8—H8 | 119.6 | C17—C18—C19 | 119.1 (3) |
C8—C9—C10 | 118.57 (18) | C17—C18—H18 | 120.5 |
C8—C9—C12 | 121.89 (17) | C19—C18—H18 | 120.5 |
C10—C9—C12 | 119.51 (18) | C20—C19—C18 | 120.4 (2) |
C11—C10—C9 | 121.43 (17) | C20—C19—H19 | 119.8 |
C11—C10—H10 | 119.3 | C18—C19—H19 | 119.8 |
C9—C10—H10 | 119.3 | C19—C20—C15 | 120.8 (2) |
C6—C11—C10 | 118.07 (17) | C19—C20—H20 | 119.6 |
C6—C11—H11 | 121.0 | C15—C20—H20 | 119.6 |
| | | |
C5—O1—N2—N3 | −0.8 (2) | C7—C6—C11—C10 | −2.1 (3) |
O1—N2—N3—C4 | 0.7 (2) | N3—C6—C11—C10 | 178.19 (16) |
O1—N2—N3—C6 | 179.20 (13) | C9—C10—C11—C6 | −1.0 (3) |
N2—N3—C4—C5 | −0.3 (2) | C8—C9—C12—O12 | 167.1 (2) |
C6—N3—C4—C5 | −178.63 (16) | C10—C9—C12—O12 | −11.2 (3) |
N3—C4—C5—O5 | 179.8 (3) | C8—C9—C12—C13 | −12.4 (3) |
N3—C4—C5—O1 | −0.2 (2) | C10—C9—C12—C13 | 169.35 (18) |
N2—O1—C5—O5 | −179.41 (19) | O12—C12—C13—C14 | −1.5 (4) |
N2—O1—C5—C4 | 0.6 (2) | C9—C12—C13—C14 | 177.95 (19) |
N2—N3—C6—C11 | −164.01 (17) | C12—C13—C14—C15 | −177.77 (19) |
C4—N3—C6—C11 | 14.3 (3) | C13—C14—C15—C16 | 3.1 (3) |
N2—N3—C6—C7 | 16.2 (2) | C13—C14—C15—C20 | −177.7 (2) |
C4—N3—C6—C7 | −165.45 (18) | C20—C15—C16—C17 | 0.0 (3) |
C11—C6—C7—C8 | 3.4 (3) | C14—C15—C16—C17 | 179.2 (2) |
N3—C6—C7—C8 | −176.89 (16) | C15—C16—C17—C18 | 0.3 (4) |
C6—C7—C8—C9 | −1.6 (3) | C16—C17—C18—C19 | −0.2 (4) |
C7—C8—C9—C10 | −1.3 (3) | C17—C18—C19—C20 | 0.0 (4) |
C7—C8—C9—C12 | −179.60 (18) | C18—C19—C20—C15 | 0.3 (4) |
C8—C9—C10—C11 | 2.7 (3) | C16—C15—C20—C19 | −0.3 (3) |
C12—C9—C10—C11 | −179.03 (18) | C14—C15—C20—C19 | −179.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O5i | 0.93 | 2.28 | 3.187 (2) | 164 |
C11—H11···O5i | 0.93 | 2.51 | 3.429 (3) | 169 |
C20—H20···O12ii | 0.93 | 2.54 | 3.285 (3) | 137 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.