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The title compound, C14H10N2O2, is one of many sydnones which have been synthesized in order to investigate the influence of substituents and sydnone-ring stability. There is medicinal interest in the sydnone if the ring can predictably release NO. Bond lengths and angles of the sydnone ring were compared with those of other published sydnone compounds and were found to fit the average of the published data.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010773/su6100sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010773/su6100Isup2.hkl
Contains datablock I

CCDC reference: 242317

Key indicators

  • Single-crystal synchrotron study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.146
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.46
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: MarControl (MARResearch, 2000); cell refinement: DENZO (Otwinowski and Minor, 1997); data reduction: SCALEPACK (Fox and Holmes, 1966); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1994); software used to prepare material for publication: OSCAIL (McArdle, 2003).

3-(2-biphenyl)sydnone top
Crystal data top
C14H10N2O2F(000) = 496
Mr = 238.24Dx = 1.408 Mg m3
Monoclinic, P21/nMelting point: 418 K
Hall symbol: -P 2ynSynchrotron radiation, λ = 0.70998 Å
a = 11.012 (15) ÅCell parameters from 25 reflections
b = 8.310 (15) Åθ = 12–18°
c = 12.941 (15) ŵ = 0.10 mm1
β = 108.406 (15)°T = 298 K
V = 1124 (3) Å3Rectangle, colourless
Z = 40.40 × 0.35 × 0.10 mm
Data collection top
Mar CCD area-detector
diffractometer
2019 reflections with I > 2σ(I)
Radiation source: synchrotronRint = 0.031
Graphite monochromatorθmax = 26.7°, θmin = 2.1°
ω scansh = 1313
16475 measured reflectionsk = 1010
2210 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.6398P]
where P = (Fo2 + 2Fc2)/3
2210 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 8.9323 (0.0167) x - 3.3884 (0.0079) y - 1.8338 (0.0095) z = 0.1800 (0.0028)

* -0.0044 (0.0011) C7 * 0.0031 (0.0012) C8 * 0.0016 (0.0011) C9 * -0.0050 (0.0012) C10 * 0.0036 (0.0012) C11 * 0.0011 (0.0011) C12

Rms deviation of fitted atoms = 0.0034

10.6173 (0.0193) x - 2.0520 (0.0062) y - 5.1315 (0.0119) z = 2.7448 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 50.16 (0.11)

* 0.0071 (0.0010) C1' * -0.0128 (0.0010) C2' * 0.0077 (0.0011) C3' * 0.0036 (0.0011) C4' * -0.0097 (0.0011) C5' * 0.0042 (0.0010) C6'

Rms deviation of fitted atoms = 0.0081

5.3124 (0.0126) x - 4.0690 (0.0094) y + 6.9470 (0.0155) z = 2.4431 (0.0047)

Angle to previous plane (with approximate e.s.d.) = 58.97 (0.12)

* -0.0079 (0.0010) C4 * 0.0078 (0.0009) C5 * -0.0054 (0.0010) O1 * 0.0005 (0.0010) N2 * 0.0050 (0.0010) N3

Rms deviation of fitted atoms = 0.0060

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*/Ueq
O50.44588 (12)1.14144 (13)1.10069 (10)0.0285 (3)
O10.28415 (12)1.02296 (13)1.14705 (10)0.0277 (3)
N20.21119 (15)0.88504 (16)1.12291 (13)0.0269 (4)
C1'0.19971 (15)0.65566 (17)1.01464 (13)0.0208 (4)
C5'0.17153 (16)0.38668 (19)1.06716 (15)0.0258 (4)
H5'0.18050.30851.12050.031*
C2'0.13860 (15)0.62399 (17)0.90473 (14)0.0208 (4)
N30.25200 (13)0.81280 (15)1.05005 (11)0.0201 (3)
C6'0.21655 (16)0.54137 (18)1.09574 (14)0.0230 (4)
H6'0.25740.56801.16820.028*
C3'0.09731 (16)0.46585 (18)0.87856 (15)0.0245 (4)
H3'0.05840.43790.80600.029*
C4'0.11319 (16)0.34974 (19)0.95864 (15)0.0268 (4)
H4'0.08420.24550.93910.032*
C40.34393 (15)0.88986 (18)1.02302 (14)0.0219 (4)
H40.38240.85710.97210.026*
C50.37117 (16)1.03043 (18)1.08679 (14)0.0222 (4)
C70.11251 (15)0.74965 (18)0.81879 (13)0.0216 (4)
C80.14163 (16)0.72250 (19)0.72304 (14)0.0243 (4)
H80.17950.62600.71350.029*
C90.11455 (16)0.8382 (2)0.64202 (14)0.0258 (4)
H90.13450.81900.57840.031*
C100.05779 (16)0.98262 (19)0.65513 (14)0.0258 (4)
H100.04051.06050.60080.031*
C110.02689 (16)1.01049 (19)0.74951 (14)0.0248 (4)
H110.01211.10660.75810.030*
C120.05423 (16)0.89503 (18)0.83104 (14)0.0239 (4)
H120.03370.91430.89430.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0357 (7)0.0162 (6)0.0388 (7)0.0069 (5)0.0193 (6)0.0025 (5)
O10.0410 (7)0.0152 (6)0.0373 (7)0.0056 (5)0.0271 (6)0.0058 (5)
N20.0379 (8)0.0154 (6)0.0385 (8)0.0040 (5)0.0277 (7)0.0049 (5)
C1'0.0236 (7)0.0125 (7)0.0337 (9)0.0008 (5)0.0196 (7)0.0004 (6)
C5'0.0309 (9)0.0149 (7)0.0391 (10)0.0025 (6)0.0218 (8)0.0051 (6)
C2'0.0228 (7)0.0138 (7)0.0320 (9)0.0015 (5)0.0174 (7)0.0004 (6)
N30.0253 (7)0.0129 (6)0.0280 (7)0.0020 (5)0.0171 (6)0.0004 (5)
C6'0.0268 (8)0.0167 (7)0.0320 (9)0.0022 (6)0.0185 (7)0.0018 (6)
C3'0.0276 (8)0.0142 (7)0.0364 (10)0.0002 (6)0.0167 (7)0.0026 (6)
C4'0.0308 (9)0.0127 (7)0.0438 (10)0.0007 (6)0.0215 (8)0.0011 (6)
C40.0269 (8)0.0145 (7)0.0314 (9)0.0012 (6)0.0193 (7)0.0006 (6)
C50.0276 (8)0.0142 (7)0.0304 (9)0.0010 (6)0.0170 (7)0.0018 (6)
C70.0230 (7)0.0150 (7)0.0309 (9)0.0011 (6)0.0146 (7)0.0014 (6)
C80.0267 (8)0.0179 (7)0.0330 (9)0.0014 (6)0.0165 (7)0.0024 (6)
C90.0288 (8)0.0251 (8)0.0285 (9)0.0018 (6)0.0162 (8)0.0012 (6)
C100.0286 (8)0.0198 (8)0.0318 (9)0.0035 (6)0.0136 (8)0.0024 (6)
C110.0276 (8)0.0160 (7)0.0334 (9)0.0009 (6)0.0134 (8)0.0010 (6)
C120.0276 (8)0.0149 (7)0.0347 (9)0.0010 (6)0.0179 (7)0.0012 (6)
Geometric parameters (Å, º) top
O5—C51.211 (2)C3'—H3'0.9300
O1—N21.378 (3)C4'—H4'0.9300
O1—C51.415 (2)C4—C51.407 (3)
N2—N31.311 (2)C4—H40.9300
C1'—C6'1.384 (3)C7—C81.393 (3)
C1'—C2'1.393 (3)C7—C121.400 (3)
C1'—N31.442 (3)C8—C91.384 (3)
C5'—C4'1.382 (3)C8—H80.9300
C5'—C6'1.385 (3)C9—C101.388 (3)
C5'—H5'0.9300C9—H90.9300
C2'—C3'1.397 (3)C10—C111.387 (3)
C2'—C71.486 (3)C10—H100.9300
N3—C41.335 (2)C11—C121.387 (3)
C6'—H6'0.9300C11—H110.9300
C3'—C4'1.386 (3)C12—H120.9300
N2—O1—C5111.06 (12)N3—C4—H4126.8
N3—N2—O1103.66 (14)C5—C4—H4126.8
C6'—C1'—C2'123.41 (17)O5—C5—C4136.77 (16)
C6'—C1'—N3115.84 (17)O5—C5—O1119.87 (15)
C2'—C1'—N3120.74 (14)C4—C5—O1103.35 (14)
C4'—C5'—C6'119.33 (15)C8—C7—C12118.88 (15)
C4'—C5'—H5'120.3C8—C7—C2'120.51 (16)
C6'—C5'—H5'120.3C12—C7—C2'120.58 (16)
C1'—C2'—C3'116.14 (15)C9—C8—C7120.43 (17)
C1'—C2'—C7123.25 (16)C9—C8—H8119.8
C3'—C2'—C7120.56 (18)C7—C8—H8119.8
N2—N3—C4115.44 (15)C8—C9—C10120.38 (17)
N2—N3—C1'116.74 (13)C8—C9—H9119.8
C4—N3—C1'127.66 (13)C10—C9—H9119.8
C1'—C6'—C5'118.91 (18)C11—C10—C9119.81 (16)
C1'—C6'—H6'120.5C11—C10—H10120.1
C5'—C6'—H6'120.5C9—C10—H10120.1
C4'—C3'—C2'121.27 (19)C10—C11—C12119.98 (17)
C4'—C3'—H3'119.4C10—C11—H11120.0
C2'—C3'—H3'119.4C12—C11—H11120.0
C5'—C4'—C3'120.91 (17)C11—C12—C7120.52 (17)
C5'—C4'—H4'119.5C11—C12—H12119.7
C3'—C4'—H4'119.5C7—C12—H12119.7
N3—C4—C5106.47 (15)
C5—O1—N2—N30.52 (18)N2—N3—C4—C51.3 (2)
C6'—C1'—C2'—C3'2.0 (2)C1'—N3—C4—C5173.79 (15)
N3—C1'—C2'—C3'176.79 (13)N3—C4—C5—O5177.0 (2)
C6'—C1'—C2'—C7175.53 (14)N3—C4—C5—O11.47 (17)
N3—C1'—C2'—C75.7 (2)N2—O1—C5—O5177.56 (15)
O1—N2—N3—C40.51 (19)N2—O1—C5—C41.26 (18)
O1—N2—N3—C1'175.15 (13)C1'—C2'—C7—C8132.61 (18)
C6'—C1'—N3—N257.4 (2)C3'—C2'—C7—C849.9 (2)
C2'—C1'—N3—N2123.71 (18)C1'—C2'—C7—C1249.6 (2)
C6'—C1'—N3—C4117.66 (19)C3'—C2'—C7—C12127.84 (18)
C2'—C1'—N3—C461.2 (2)C12—C7—C8—C90.7 (2)
C2'—C1'—C6'—C5'0.5 (2)C2'—C7—C8—C9178.50 (15)
N3—C1'—C6'—C5'178.40 (13)C7—C8—C9—C100.1 (2)
C4'—C5'—C6'—C1'1.1 (2)C8—C9—C10—C110.7 (2)
C1'—C2'—C3'—C4'2.0 (2)C9—C10—C11—C120.8 (2)
C7—C2'—C3'—C4'175.59 (14)C10—C11—C12—C70.3 (2)
C6'—C5'—C4'—C3'1.1 (2)C8—C7—C12—C110.5 (2)
C2'—C3'—C4'—C5'0.5 (2)C2'—C7—C12—C11178.31 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O5i0.932.363.214 (6)152
C6—H6···O1ii0.932.603.335 (6)136
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1/2, y1/2, z+5/2.
 

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