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The three title compounds, i.e. C14H8N2O4S, (I), C16H10N2O4, (II), and C18H14N2O6, (III), respectively, are almost planar. The benzoxazinone and nitro­aryl moieties are in a trans configuration with respect to the ethyl­ene group. The nitro group in all three mol­ecules is almost coplanar with the aryl substituent and shows quite strong conjugation with the rest of the [pi]-system of the mol­ecules. The mol­ecules of (I) form layers along the crystallographic b axis, with a distance between adjacent layers of about 3.5 Å. However, the mol­ecules of (II) and (III) form stacks, with distances between adjacent mol­ecules of about 6.0 and 3.6 Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001057X/qd0005sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001057X/qd0005Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001057X/qd0005IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001057X/qd0005IIIsup4.hkl
Contains datablock III

CCDC references: 150741; 150742; 150743

Computing details top

For all compounds, data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C14H8N2O4SDx = 1.569 Mg m3
Mr = 300.28Melting point = 217–219 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
a = 7.0127 (11) ÅCell parameters from 24 reflections
b = 12.524 (2) Åθ = 10–13°
c = 14.477 (3) ŵ = 0.27 mm1
V = 1271.5 (4) Å3T = 293 K
Z = 4Parallelepiped, yellow
F(000) = 6160.40 × 0.20 × 0.20 mm
Data collection top
Siemens P3/PC
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 1.6°
Graphite monochromatorh = 09
θ/2θ scansk = 017
1938 measured reflectionsl = 020
1938 independent reflections2 standard reflections every 98 reflections
1073 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051H atoms: see below
wR(F2) = 0.100Calculated w = 1/[σ2(Fo2) + (0.0589P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
1903 reflectionsΔρmax = 0.24 e Å3
190 parametersΔρmin = 0.27 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.25 (14)
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 on F2 for ALL reflections except for 35 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
S10.00976 (15)0.71741 (8)0.75978 (9)0.0436 (2)
O10.1099 (4)0.8751 (2)0.4286 (2)0.0397 (6)
O20.2030 (5)1.0363 (2)0.3868 (2)0.0553 (8)
O40.1771 (5)0.5081 (2)0.9293 (2)0.0632 (9)
O30.0302 (6)0.6583 (3)0.9510 (2)0.0740 (11)
N10.0093 (5)0.7465 (3)0.3241 (3)0.0423 (8)
N20.0923 (6)0.5873 (3)0.9010 (2)0.0496 (9)
C10.0208 (5)0.7867 (3)0.1615 (3)0.0423 (9)
H10.0701 (5)0.7191 (3)0.1498 (3)0.051*
C20.0104 (6)0.8572 (3)0.0898 (3)0.0426 (9)
H20.0188 (6)0.8363 (3)0.0298 (3)0.051*
C30.0839 (6)0.9577 (3)0.1050 (3)0.0440 (9)
H30.1041 (6)1.0038 (3)0.0557 (3)0.053*
C40.1273 (5)0.9897 (3)0.1937 (2)0.0375 (8)
H40.1766 (5)1.0576 (3)0.2043 (2)0.045*
C50.0969 (5)0.9198 (3)0.2678 (3)0.0334 (7)
C60.0217 (5)0.8175 (3)0.2509 (3)0.0338 (8)
C70.1409 (5)0.9522 (3)0.3621 (2)0.0361 (8)
C80.0334 (5)0.7779 (3)0.4047 (3)0.0366 (9)
C90.0006 (5)0.7100 (3)0.4854 (3)0.0407 (9)
H90.0453 (5)0.6414 (3)0.4747 (3)0.049*
C100.0307 (5)0.7378 (3)0.5721 (3)0.0402 (9)
H100.0790 (5)0.8056 (3)0.5840 (3)0.048*
C110.0081 (5)0.6677 (3)0.6499 (3)0.0383 (8)
C120.0693 (6)0.5631 (3)0.6504 (3)0.0441 (10)
H120.0867 (6)0.5226 (3)0.5971 (3)0.053*
C130.1025 (6)0.5244 (3)0.7394 (3)0.0448 (9)
H130.1435 (6)0.4554 (3)0.7524 (3)0.054*
C140.0680 (5)0.5992 (3)0.8039 (3)0.0401 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0509 (5)0.0373 (4)0.0424 (4)0.0070 (5)0.0018 (5)0.0022 (5)
O10.044 (2)0.0402 (13)0.0344 (12)0.0086 (12)0.0038 (12)0.0006 (11)
O20.075 (2)0.0452 (15)0.0459 (15)0.024 (2)0.0012 (15)0.0048 (13)
O40.086 (2)0.0522 (15)0.051 (2)0.0052 (15)0.022 (2)0.0102 (15)
O30.107 (3)0.072 (2)0.043 (2)0.003 (2)0.003 (2)0.010 (2)
N10.050 (2)0.035 (2)0.042 (2)0.0009 (15)0.0001 (14)0.0012 (14)
N20.059 (2)0.051 (2)0.039 (2)0.012 (2)0.004 (2)0.002 (2)
C10.045 (2)0.040 (2)0.043 (2)0.003 (2)0.002 (2)0.012 (2)
C20.044 (2)0.053 (2)0.031 (2)0.004 (2)0.002 (2)0.009 (2)
C30.043 (2)0.050 (2)0.039 (2)0.005 (2)0.002 (2)0.004 (2)
C40.038 (2)0.039 (2)0.035 (2)0.001 (2)0.005 (2)0.000 (2)
C50.029 (2)0.036 (2)0.035 (2)0.0014 (14)0.001 (2)0.0026 (14)
C60.035 (2)0.032 (2)0.034 (2)0.0038 (14)0.002 (2)0.003 (2)
C70.036 (2)0.037 (2)0.035 (2)0.005 (2)0.003 (2)0.0018 (15)
C80.035 (2)0.033 (2)0.042 (2)0.001 (2)0.004 (2)0.003 (2)
C90.048 (2)0.033 (2)0.042 (2)0.001 (2)0.000 (2)0.004 (2)
C100.037 (2)0.041 (2)0.042 (2)0.006 (2)0.002 (2)0.004 (2)
C110.041 (2)0.038 (2)0.036 (2)0.000 (2)0.002 (2)0.0031 (15)
C120.059 (3)0.037 (2)0.037 (2)0.006 (2)0.003 (2)0.001 (2)
C130.052 (2)0.035 (2)0.047 (2)0.004 (2)0.001 (2)0.006 (2)
C140.044 (2)0.037 (2)0.040 (2)0.002 (2)0.003 (2)0.006 (2)
Geometric parameters (Å, º) top
S1—C141.702 (4)C2—C31.379 (6)
S1—C111.712 (4)C3—C41.378 (5)
O1—C81.374 (4)C4—C51.401 (5)
O1—C71.381 (4)C5—C61.407 (5)
O2—C71.195 (4)C5—C71.457 (5)
O4—N21.228 (4)C8—C91.464 (5)
O3—N21.227 (5)C9—C101.320 (6)
N1—C81.267 (5)C10—C111.455 (5)
N1—C61.400 (5)C11—C121.379 (5)
N2—C141.423 (5)C12—C131.396 (5)
C1—C21.380 (6)C13—C141.345 (5)
C1—C61.384 (5)
C14—S1—C1190.5 (2)O2—C7—O1117.7 (3)
C8—O1—C7120.3 (3)O2—C7—C5127.1 (3)
C8—N1—C6117.6 (4)O1—C7—C5115.2 (3)
O3—N2—O4124.1 (4)N1—C8—O1126.8 (3)
O3—N2—C14117.7 (4)N1—C8—C9121.1 (4)
O4—N2—C14118.2 (4)O1—C8—C9112.0 (3)
C2—C1—C6119.4 (3)C10—C9—C8125.5 (4)
C3—C2—C1121.6 (4)C9—C10—C11123.2 (4)
C4—C3—C2119.8 (4)C12—C11—C10129.5 (4)
C3—C4—C5119.8 (3)C12—C11—S1111.4 (3)
C4—C5—C6119.5 (3)C10—C11—S1119.1 (3)
C4—C5—C7120.8 (3)C11—C12—C13112.7 (4)
C6—C5—C7119.7 (3)C14—C13—C12111.7 (3)
C1—C6—N1119.8 (3)C13—C14—N2126.3 (3)
C1—C6—C5119.8 (3)C13—C14—S1113.7 (3)
N1—C6—C5120.3 (4)N2—C14—S1120.0 (3)
C6—C1—C2—C30.3 (6)C7—O1—C8—N12.6 (6)
C1—C2—C3—C40.2 (6)C7—O1—C8—C9176.4 (3)
C2—C3—C4—C50.1 (6)N1—C8—C9—C10176.1 (4)
C3—C4—C5—C60.2 (5)O1—C8—C9—C103.0 (6)
C3—C4—C5—C7179.7 (4)C8—C9—C10—C11178.7 (3)
C2—C1—C6—N1179.9 (4)C9—C10—C11—C123.9 (7)
C2—C1—C6—C50.3 (5)C9—C10—C11—S1172.4 (3)
C8—N1—C6—C1179.3 (3)C14—S1—C11—C120.9 (3)
C8—N1—C6—C50.3 (5)C14—S1—C11—C10176.0 (3)
C4—C5—C6—C10.2 (5)C10—C11—C12—C13176.1 (4)
C7—C5—C6—C1179.8 (3)S1—C11—C12—C130.4 (5)
C4—C5—C6—N1179.9 (3)C11—C12—C13—C140.5 (6)
C7—C5—C6—N10.5 (5)C12—C13—C14—N2178.2 (4)
C8—O1—C7—O2178.1 (3)C12—C13—C14—S11.2 (5)
C8—O1—C7—C53.2 (5)O3—N2—C14—C13170.4 (4)
C4—C5—C7—O20.4 (6)O4—N2—C14—C1311.0 (6)
C6—C5—C7—O2179.2 (4)O3—N2—C14—S110.2 (5)
C4—C5—C7—O1178.2 (3)O4—N2—C14—S1168.4 (3)
C6—C5—C7—O12.3 (5)C11—S1—C14—C131.2 (3)
C6—N1—C8—O10.7 (6)C11—S1—C14—N2178.2 (3)
C6—N1—C8—C9178.3 (3)
(II) top
Crystal data top
C16H10N2O4Dx = 1.462 Mg m3
Mr = 294.26Melting point = 237–239 K
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 14.627 (3) ÅCell parameters from 24 reflections
b = 7.491 (2) Åθ = 9–10°
c = 12.344 (5) ŵ = 0.11 mm1
β = 98.71 (3)°T = 213 K
V = 1337.0 (7) Å3Parallelepiped, yellow
Z = 40.30 × 0.20 × 0.20 mm
F(000) = 608
Data collection top
Syntex P21/PC
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 2.8°
Graphite monochromatorh = 020
θ/2θ scansk = 010
2042 measured reflectionsl = 1717
2042 independent reflections2 standard reflections every 98 reflections
1011 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081H atoms: see below
wR(F2) = 0.178Calculated w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
2004 reflectionsΔρmax = 0.51 e Å3
199 parametersΔρmin = 0.26 e Å3
2 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (20)
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 on F2 for ALL reflections except for 38 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O10.7222 (2)0.1198 (5)0.1953 (3)0.0428 (9)
O20.7517 (3)0.2956 (6)0.0621 (3)0.0556 (11)
O30.1929 (3)0.1458 (7)0.4408 (4)0.0614 (13)
O40.2773 (3)0.2381 (8)0.5889 (4)0.076 (2)
N10.8348 (3)0.0393 (6)0.3137 (4)0.0419 (11)
N20.2673 (3)0.1752 (6)0.4957 (4)0.0443 (12)
C10.9944 (4)0.0321 (8)0.2795 (5)0.0458 (13)
H11.0120 (4)0.1023 (8)0.3423 (5)0.055*
C21.0589 (4)0.0192 (9)0.2155 (6)0.056 (2)
H21.1199 (4)0.0230 (9)0.2322 (6)0.067*
C31.0352 (4)0.1335 (10)0.1254 (6)0.057 (2)
H31.0804 (4)0.1738 (10)0.0847 (6)0.068*
C40.9443 (4)0.1854 (9)0.0980 (5)0.051 (2)
H40.9269 (4)0.2580 (9)0.0362 (5)0.061*
C50.8787 (4)0.1317 (7)0.1603 (5)0.0410 (13)
C60.9016 (3)0.0215 (7)0.2503 (4)0.0351 (12)
C70.7829 (3)0.1946 (8)0.1319 (5)0.0418 (13)
C80.7522 (4)0.0056 (7)0.2827 (4)0.0357 (11)
C90.6745 (4)0.0496 (7)0.3358 (4)0.0406 (12)
H90.6878 (4)0.1270 (7)0.3960 (4)0.049*
C100.5891 (4)0.0030 (7)0.3086 (5)0.0467 (14)
H100.5772 (4)0.0732 (7)0.2476 (5)0.056*
C110.5082 (3)0.0514 (7)0.3587 (5)0.0396 (13)
C120.5138 (3)0.1603 (7)0.4547 (4)0.0392 (12)
H120.5710 (3)0.2069 (7)0.4877 (4)0.047*
C130.4349 (4)0.1959 (8)0.4978 (5)0.0450 (13)
H130.4382 (4)0.2657 (8)0.5616 (5)0.054*
C140.3514 (3)0.1310 (7)0.4492 (4)0.0350 (11)
C150.3431 (4)0.0251 (7)0.3575 (5)0.0416 (13)
H150.2852 (4)0.0198 (7)0.3256 (5)0.050*
C160.4213 (4)0.0136 (8)0.3135 (5)0.0440 (14)
H160.4163 (4)0.0863 (8)0.2509 (5)0.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.029 (2)0.047 (2)0.055 (2)0.003 (2)0.015 (2)0.009 (2)
O20.048 (2)0.064 (3)0.057 (3)0.001 (2)0.013 (2)0.016 (2)
O30.032 (2)0.089 (4)0.063 (3)0.011 (2)0.011 (2)0.009 (2)
O40.056 (3)0.103 (4)0.076 (3)0.022 (3)0.033 (2)0.052 (3)
N10.028 (2)0.044 (2)0.055 (3)0.003 (2)0.012 (2)0.002 (2)
N20.038 (2)0.042 (3)0.059 (3)0.009 (2)0.026 (2)0.004 (2)
C10.038 (3)0.055 (3)0.044 (3)0.008 (3)0.006 (2)0.002 (3)
C20.032 (3)0.068 (4)0.069 (4)0.001 (3)0.008 (3)0.014 (3)
C30.036 (3)0.079 (4)0.060 (4)0.014 (3)0.017 (3)0.013 (3)
C40.051 (3)0.064 (4)0.042 (3)0.013 (3)0.021 (3)0.003 (3)
C50.034 (2)0.046 (3)0.043 (3)0.001 (2)0.004 (2)0.007 (3)
C60.027 (2)0.037 (3)0.041 (3)0.001 (2)0.002 (2)0.010 (2)
C70.032 (3)0.045 (3)0.049 (3)0.008 (2)0.007 (2)0.007 (3)
C80.035 (3)0.041 (3)0.033 (3)0.007 (2)0.011 (2)0.005 (2)
C90.036 (3)0.047 (3)0.041 (3)0.002 (2)0.013 (2)0.005 (2)
C100.040 (3)0.039 (3)0.063 (4)0.004 (3)0.015 (3)0.009 (3)
C110.033 (3)0.038 (3)0.050 (3)0.006 (2)0.016 (2)0.005 (3)
C120.034 (3)0.042 (3)0.042 (3)0.003 (2)0.004 (2)0.007 (2)
C130.049 (3)0.041 (3)0.047 (3)0.000 (3)0.012 (3)0.007 (3)
C140.033 (2)0.037 (3)0.038 (3)0.000 (2)0.014 (2)0.002 (2)
C150.029 (3)0.043 (3)0.054 (4)0.002 (2)0.007 (2)0.003 (3)
C160.043 (3)0.056 (3)0.035 (3)0.001 (3)0.014 (2)0.003 (3)
Geometric parameters (Å, º) top
O1—C71.388 (6)C4—C51.377 (8)
O1—C81.394 (6)C5—C61.384 (7)
O2—C71.185 (7)C5—C71.470 (8)
O3—N21.211 (6)C8—C91.456 (7)
O4—N21.232 (7)C9—C101.291 (8)
N1—C81.256 (7)C10—C111.462 (8)
N1—C61.417 (7)C11—C161.395 (7)
N2—C141.472 (6)C11—C121.431 (8)
C1—C21.375 (9)C12—C131.369 (8)
C1—C61.409 (7)C13—C141.366 (7)
C2—C31.404 (10)C14—C151.372 (8)
C3—C41.377 (9)C15—C161.369 (8)
C7—O1—C8122.0 (4)O1—C7—C5113.8 (5)
C8—N1—C6117.1 (4)N1—C8—O1125.2 (5)
O3—N2—O4124.1 (5)N1—C8—C9124.5 (5)
O3—N2—C14118.3 (5)O1—C8—C9110.2 (4)
O4—N2—C14117.6 (4)C10—C9—C8126.7 (6)
C2—C1—C6119.4 (6)C9—C10—C11129.5 (6)
C1—C2—C3121.1 (6)C16—C11—C12117.7 (5)
C4—C3—C2118.7 (6)C16—C11—C10119.5 (5)
C5—C4—C3120.5 (6)C12—C11—C10122.9 (5)
C4—C5—C6121.2 (5)C13—C12—C11119.1 (5)
C4—C5—C7119.5 (5)C14—C13—C12120.7 (5)
C6—C5—C7119.3 (5)C13—C14—C15122.0 (5)
C5—C6—C1118.8 (5)C13—C14—N2119.5 (4)
C5—C6—N1122.2 (4)C15—C14—N2118.5 (4)
C1—C6—N1119.0 (5)C16—C15—C14118.3 (5)
O2—C7—O1117.3 (4)C15—C16—C11122.2 (5)
O2—C7—C5128.8 (5)
C6—C1—C2—C34.1 (9)C7—O1—C8—N10.9 (8)
C1—C2—C3—C43.9 (10)C7—O1—C8—C9178.8 (4)
C2—C3—C4—C52.5 (10)N1—C8—C9—C10178.0 (5)
C3—C4—C5—C61.4 (9)O1—C8—C9—C100.1 (8)
C3—C4—C5—C7177.6 (6)C8—C9—C10—C11179.2 (5)
C4—C5—C6—C11.6 (8)C9—C10—C11—C16179.0 (6)
C7—C5—C6—C1177.4 (5)C9—C10—C11—C122.6 (9)
C4—C5—C6—N1178.2 (5)C16—C11—C12—C130.0 (8)
C7—C5—C6—N12.8 (7)C10—C11—C12—C13178.5 (5)
C2—C1—C6—C52.9 (8)C11—C12—C13—C141.1 (8)
C2—C1—C6—N1176.9 (5)C12—C13—C14—C151.5 (8)
C8—N1—C6—C52.5 (7)C12—C13—C14—N2178.4 (5)
C8—N1—C6—C1177.3 (5)O3—N2—C14—C13166.2 (5)
C8—O1—C7—O2177.1 (5)O4—N2—C14—C1314.6 (7)
C8—O1—C7—C54.4 (7)O3—N2—C14—C1513.7 (7)
C4—C5—C7—O23.3 (9)O4—N2—C14—C15165.4 (5)
C6—C5—C7—O2175.8 (6)C13—C14—C15—C160.9 (8)
C4—C5—C7—O1175.1 (5)N2—C14—C15—C16179.1 (5)
C6—C5—C7—O15.9 (7)C14—C15—C16—C110.2 (8)
C6—N1—C8—O14.5 (8)C12—C11—C16—C150.6 (8)
C6—N1—C8—C9177.9 (5)C10—C11—C16—C15179.2 (5)
(III) top
Crystal data top
C18H14N2O6F(000) = 368
Mr = 354.31Dx = 1.483 Mg m3
Triclinic, P1Melting point = 271–273 K
a = 6.8484 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2348 (14) ÅCell parameters from 30 reflections
c = 16.806 (3) Åθ = 10–13°
α = 93.801 (15)°µ = 0.11 mm1
β = 96.783 (13)°T = 208 K
γ = 105.321 (13)°Parallelepiped, yellow
V = 793.3 (2) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Syntex P21/PC
diffractometer
Rint = 0.026
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.2°
Graphite monochromatorh = 68
θ/2θ scansk = 88
3051 measured reflectionsl = 1919
2792 independent reflections2 standard reflections every 98 reflections
1723 reflections with I > 2σ(I) intensity decay: none
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)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.101H atoms: see below
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0595P)2 + 0.0324P]
where P = (Fo2 + 2Fc2)/3
2727 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.23 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.

Refinement. Refinement on F2 for ALL reflections except for 65 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O10.7447 (2)0.2485 (2)0.08201 (9)0.0328 (4)
O21.0598 (2)0.3411 (3)0.11130 (9)0.0413 (5)
O30.2058 (3)0.4578 (3)0.36360 (10)0.0603 (6)
O40.0891 (3)0.3593 (3)0.29043 (11)0.0557 (6)
O50.5763 (3)0.1354 (2)0.43977 (9)0.0453 (5)
O60.9542 (3)0.0596 (2)0.41253 (9)0.0437 (5)
N10.4612 (3)0.0670 (3)0.17394 (11)0.0305 (5)
N20.0971 (3)0.3945 (3)0.29916 (12)0.0381 (5)
C10.5129 (4)0.0386 (3)0.30661 (13)0.0338 (6)
H10.3733 (4)0.1055 (3)0.31775 (13)0.041*
C20.6379 (4)0.0404 (3)0.36500 (13)0.0344 (6)
C30.8467 (4)0.0640 (3)0.34945 (13)0.0335 (6)
C40.9265 (4)0.1582 (3)0.27480 (13)0.0330 (6)
H41.0666 (4)0.2230 (3)0.26351 (13)0.040*
C50.8005 (3)0.1586 (3)0.21507 (12)0.0276 (5)
C60.5930 (3)0.0627 (3)0.23073 (12)0.0275 (5)
C70.8853 (3)0.2568 (3)0.13567 (13)0.0310 (5)
C80.5399 (3)0.1592 (3)0.10479 (13)0.0282 (5)
C90.4198 (4)0.1803 (3)0.04135 (13)0.0316 (6)
H90.2794 (4)0.1160 (3)0.05028 (13)0.038*
C100.4957 (3)0.2850 (3)0.02876 (13)0.0303 (5)
H100.6361 (3)0.3491 (3)0.03605 (13)0.036*
C110.3845 (3)0.3117 (3)0.09609 (12)0.0278 (5)
C120.1732 (3)0.2416 (3)0.09265 (13)0.0331 (6)
H120.0943 (3)0.1761 (3)0.04442 (13)0.040*
C130.0783 (3)0.2665 (3)0.15876 (14)0.0329 (6)
H130.0640 (3)0.2173 (3)0.15631 (14)0.039*
C140.1962 (3)0.3651 (3)0.22857 (13)0.0297 (5)
C150.4043 (4)0.4386 (3)0.23412 (14)0.0354 (6)
H150.4816 (4)0.5052 (3)0.28244 (14)0.042*
C160.4979 (3)0.4131 (3)0.16744 (13)0.0330 (6)
H160.6400 (3)0.4649 (3)0.17020 (13)0.040*
C170.3690 (4)0.2523 (4)0.45761 (15)0.0551 (8)
H17A0.3468 (9)0.319 (2)0.5112 (5)0.083*
H17B0.2770 (4)0.1711 (5)0.4552 (11)0.083*
H17C0.3426 (9)0.3455 (18)0.4185 (7)0.083*
C181.1432 (4)0.2031 (4)0.4084 (2)0.0491 (7)
H18A1.1928 (14)0.1998 (18)0.4600 (4)0.074*
H18B1.2423 (9)0.1786 (15)0.3672 (8)0.074*
H18C1.1236 (7)0.3289 (4)0.3951 (11)0.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0263 (9)0.0445 (10)0.0257 (8)0.0067 (7)0.0067 (7)0.0032 (7)
O20.0279 (10)0.0609 (12)0.0303 (9)0.0067 (8)0.0030 (7)0.0060 (8)
O30.0634 (13)0.087 (2)0.0282 (10)0.0221 (11)0.0057 (9)0.0117 (10)
O40.0407 (12)0.0661 (13)0.0532 (12)0.0012 (9)0.0242 (9)0.0118 (10)
O50.0489 (11)0.0476 (11)0.0276 (9)0.0054 (8)0.0092 (8)0.0091 (8)
O60.0435 (11)0.0498 (11)0.0316 (9)0.0009 (8)0.0173 (8)0.0069 (8)
N10.0298 (11)0.0326 (11)0.0280 (10)0.0056 (8)0.0071 (8)0.0013 (8)
N20.0418 (14)0.0375 (12)0.0339 (12)0.0071 (10)0.0133 (10)0.0019 (9)
C10.0348 (14)0.0322 (14)0.0303 (13)0.0012 (10)0.0068 (11)0.0038 (10)
C20.0429 (15)0.0302 (13)0.0261 (13)0.0028 (11)0.0068 (11)0.0001 (10)
C30.0412 (15)0.0347 (14)0.0254 (13)0.0083 (11)0.0136 (11)0.0019 (10)
C40.0306 (13)0.0350 (13)0.0317 (13)0.0056 (10)0.0075 (10)0.0003 (10)
C50.0309 (13)0.0282 (12)0.0245 (12)0.0085 (10)0.0055 (10)0.0034 (9)
C60.0335 (14)0.0263 (12)0.0227 (12)0.0074 (10)0.0060 (10)0.0026 (9)
C70.0305 (14)0.0365 (13)0.0282 (12)0.0109 (11)0.0075 (10)0.0044 (10)
C80.0264 (13)0.0310 (13)0.0276 (12)0.0081 (10)0.0044 (10)0.0029 (10)
C90.0297 (13)0.0324 (13)0.0323 (13)0.0060 (10)0.0089 (10)0.0029 (10)
C100.0291 (13)0.0309 (13)0.0312 (12)0.0081 (10)0.0068 (10)0.0034 (10)
C110.0319 (13)0.0269 (12)0.0253 (12)0.0088 (10)0.0052 (10)0.0028 (10)
C120.0306 (13)0.0378 (14)0.0273 (12)0.0052 (10)0.0032 (10)0.0035 (10)
C130.0264 (13)0.0343 (13)0.0339 (13)0.0023 (10)0.0056 (10)0.0037 (10)
C140.0357 (14)0.0279 (12)0.0275 (12)0.0091 (10)0.0125 (10)0.0012 (9)
C150.0338 (14)0.0381 (14)0.0295 (13)0.0052 (11)0.0002 (10)0.0035 (11)
C160.0275 (13)0.0390 (14)0.0313 (13)0.0064 (10)0.0071 (10)0.0013 (11)
C170.055 (2)0.058 (2)0.0337 (15)0.0121 (14)0.0043 (13)0.0096 (13)
C180.039 (2)0.058 (2)0.043 (2)0.0022 (13)0.0192 (12)0.0081 (13)
Geometric parameters (Å, º) top
O1—C81.376 (2)C2—C31.413 (3)
O1—C71.387 (3)C3—C41.366 (3)
O2—C71.198 (3)C4—C51.399 (3)
O3—N21.225 (3)C5—C61.392 (3)
O4—N21.222 (2)C5—C71.448 (3)
O5—C21.355 (3)C8—C91.445 (3)
O5—C171.433 (3)C9—C101.327 (3)
O6—C31.363 (3)C10—C111.466 (3)
O6—C181.420 (3)C11—C161.393 (3)
N1—C81.283 (3)C11—C121.394 (3)
N1—C61.393 (3)C12—C131.377 (3)
N2—C141.465 (3)C13—C141.378 (3)
C1—C21.378 (3)C14—C151.373 (3)
C1—C61.401 (3)C15—C161.380 (3)
C8—O1—C7121.6 (2)N1—C6—C1118.8 (2)
C2—O5—C17117.5 (2)O2—C7—O1117.2 (2)
C3—O6—C18117.2 (2)O2—C7—C5127.9 (2)
C8—N1—C6117.2 (2)O1—C7—C5114.9 (2)
O4—N2—O3123.3 (2)N1—C8—O1124.9 (2)
O4—N2—C14118.4 (2)N1—C8—C9122.9 (2)
O3—N2—C14118.2 (2)O1—C8—C9112.2 (2)
C2—C1—C6120.2 (2)C10—C9—C8124.0 (2)
O5—C2—C1124.8 (2)C9—C10—C11127.1 (2)
O5—C2—C3114.9 (2)C16—C11—C12118.5 (2)
C1—C2—C3120.2 (2)C16—C11—C10117.7 (2)
O6—C3—C4125.0 (2)C12—C11—C10123.8 (2)
O6—C3—C2115.4 (2)C13—C12—C11121.1 (2)
C4—C3—C2119.6 (2)C12—C13—C14118.7 (2)
C3—C4—C5120.2 (2)C15—C14—C13122.1 (2)
C6—C5—C4120.6 (2)C15—C14—N2118.6 (2)
C6—C5—C7119.1 (2)C13—C14—N2119.3 (2)
C4—C5—C7120.3 (2)C14—C15—C16118.8 (2)
C5—C6—N1122.2 (2)C15—C16—C11120.9 (2)
C5—C6—C1119.0 (2)
C17—O5—C2—C14.1 (4)C6—C5—C7—O11.5 (3)
C17—O5—C2—C3176.7 (2)C4—C5—C7—O1179.4 (2)
C6—C1—C2—O5179.2 (2)C6—N1—C8—O12.1 (3)
C6—C1—C2—C31.7 (4)C6—N1—C8—C9178.0 (2)
C18—O6—C3—C418.5 (4)C7—O1—C8—N14.4 (3)
C18—O6—C3—C2162.2 (2)C7—O1—C8—C9175.6 (2)
O5—C2—C3—O62.1 (3)N1—C8—C9—C10175.6 (2)
C1—C2—C3—O6177.1 (2)O1—C8—C9—C104.5 (3)
O5—C2—C3—C4177.3 (2)C8—C9—C10—C11179.3 (2)
C1—C2—C3—C43.5 (4)C9—C10—C11—C16174.0 (2)
O6—C3—C4—C5177.9 (2)C9—C10—C11—C126.0 (4)
C2—C3—C4—C52.8 (3)C16—C11—C12—C131.9 (3)
C3—C4—C5—C60.3 (3)C10—C11—C12—C13178.1 (2)
C3—C4—C5—C7179.4 (2)C11—C12—C13—C140.9 (4)
C4—C5—C6—N1177.1 (2)C12—C13—C14—C150.0 (4)
C7—C5—C6—N13.8 (3)C12—C13—C14—N2179.4 (2)
C4—C5—C6—C11.6 (3)O4—N2—C14—C15167.5 (2)
C7—C5—C6—C1177.5 (2)O3—N2—C14—C1510.7 (3)
C8—N1—C6—C52.0 (3)O4—N2—C14—C1312.0 (3)
C8—N1—C6—C1179.3 (2)O3—N2—C14—C13169.9 (2)
C2—C1—C6—C50.9 (3)C13—C14—C15—C160.2 (4)
C2—C1—C6—N1177.9 (2)N2—C14—C15—C16179.3 (2)
C8—O1—C7—O2178.3 (2)C14—C15—C16—C111.2 (4)
C8—O1—C7—C52.3 (3)C12—C11—C16—C152.0 (3)
C6—C5—C7—O2177.7 (2)C10—C11—C16—C15178.0 (2)
C4—C5—C7—O21.4 (4)
 

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