Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062058/hk2394sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062058/hk2394Isup2.hkl |
CCDC reference: 673101
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.062
- wR factor = 0.196
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 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 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 0 ALERT type 5 Informative message, check
For a related structure, see: Zhu et al. (2007). For bond-length data, see: Allen et al. (1987).
For the preparation of the title compound, a solution of the appropriate succinyl dichloride (10 mmol) in pyridine (0.5 ml) was added to a solution of 4-nitro-phenol (20 mmol) in dry acetonitrile (30 ml) and the mixture was heated under reflux for 5–6 h. The moisture was excluded by using a calcium chloride guard tube on the reflux condenser. On cooling, the precipitates were collected, dried and recrystallized from chloroform-acetonitrile to give the title compond. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.
H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Bruker, 1997).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity. |
C16H12N2O8 | F(000) = 744 |
Mr = 360.28 | Dx = 1.490 Mg m−3 |
Monoclinic, C2/c | Melting point: 445 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.539 (13) Å | Cell parameters from 851 reflections |
b = 9.049 (9) Å | θ = 3.1–26.3° |
c = 14.662 (14) Å | µ = 0.12 mm−1 |
β = 116.609 (15)° | T = 294 K |
V = 1606 (3) Å3 | Prism, colorless |
Z = 4 | 0.20 × 0.18 × 0.14 mm |
Bruker SMART 1K CCD area-detector diffractometer | 1415 independent reflections |
Radiation source: fine-focus sealed tube | 698 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→14 |
Tmin = 0.976, Tmax = 0.983 | k = −6→10 |
3797 measured reflections | l = −17→17 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0987P)2 + 0.291P] where P = (Fo2 + 2Fc2)/3 |
1415 reflections | (Δ/σ)max = 0.001 |
118 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C16H12N2O8 | V = 1606 (3) Å3 |
Mr = 360.28 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.539 (13) Å | µ = 0.12 mm−1 |
b = 9.049 (9) Å | T = 294 K |
c = 14.662 (14) Å | 0.20 × 0.18 × 0.14 mm |
β = 116.609 (15)° |
Bruker SMART 1K CCD area-detector diffractometer | 1415 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 698 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.983 | Rint = 0.057 |
3797 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.20 e Å−3 |
1415 reflections | Δρmin = −0.26 e Å−3 |
118 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0763 (4) | −0.1228 (5) | 0.3236 (4) | 0.1213 (16) | |
O2 | −0.1973 (3) | −0.0053 (4) | 0.1964 (3) | 0.1081 (14) | |
O3 | 0.0744 (2) | 0.5257 (3) | 0.4503 (2) | 0.0595 (9) | |
O4 | 0.2214 (2) | 0.4987 (3) | 0.4210 (2) | 0.0615 (9) | |
N1 | −0.1159 (4) | −0.0091 (5) | 0.2796 (4) | 0.0771 (12) | |
C1 | 0.0807 (3) | 0.2616 (4) | 0.4553 (3) | 0.0543 (11) | |
H1 | 0.1474 | 0.2637 | 0.5144 | 0.065* | |
C2 | 0.0313 (3) | 0.1298 (4) | 0.4138 (3) | 0.0530 (11) | |
H2 | 0.0635 | 0.0408 | 0.4444 | 0.064* | |
C3 | −0.0665 (3) | 0.1317 (4) | 0.3262 (3) | 0.0505 (10) | |
C4 | −0.1169 (3) | 0.2599 (5) | 0.2803 (3) | 0.0553 (11) | |
H4 | −0.1838 | 0.2582 | 0.2215 | 0.066* | |
C5 | −0.0677 (3) | 0.3909 (5) | 0.3219 (3) | 0.0523 (11) | |
H5 | −0.1003 | 0.4800 | 0.2919 | 0.063* | |
C6 | 0.0305 (3) | 0.3890 (4) | 0.4087 (3) | 0.0458 (10) | |
C7 | 0.1701 (3) | 0.5718 (4) | 0.4517 (3) | 0.0426 (9) | |
C8 | 0.1953 (3) | 0.7226 (4) | 0.4931 (3) | 0.0526 (11) | |
H8A | 0.1934 | 0.7249 | 0.5585 | 0.063* | |
H8B | 0.1383 | 0.7889 | 0.4474 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.116 (4) | 0.071 (3) | 0.144 (4) | −0.024 (2) | 0.030 (3) | −0.024 (3) |
O2 | 0.072 (3) | 0.140 (4) | 0.092 (3) | −0.050 (2) | 0.019 (2) | −0.041 (2) |
O3 | 0.0515 (18) | 0.0563 (18) | 0.078 (2) | −0.0078 (14) | 0.0353 (16) | −0.0143 (14) |
O4 | 0.0440 (17) | 0.0658 (19) | 0.072 (2) | −0.0064 (14) | 0.0239 (16) | −0.0237 (14) |
N1 | 0.054 (3) | 0.091 (4) | 0.084 (3) | −0.028 (3) | 0.029 (3) | −0.025 (3) |
C1 | 0.039 (2) | 0.062 (3) | 0.047 (3) | 0.002 (2) | 0.006 (2) | −0.004 (2) |
C2 | 0.043 (2) | 0.056 (3) | 0.055 (3) | 0.000 (2) | 0.017 (2) | 0.000 (2) |
C3 | 0.035 (2) | 0.065 (3) | 0.054 (3) | −0.014 (2) | 0.022 (2) | −0.013 (2) |
C4 | 0.029 (2) | 0.082 (3) | 0.046 (2) | −0.003 (2) | 0.0089 (19) | −0.001 (2) |
C5 | 0.040 (2) | 0.064 (3) | 0.052 (3) | 0.006 (2) | 0.020 (2) | 0.009 (2) |
C6 | 0.036 (2) | 0.051 (2) | 0.052 (2) | −0.0056 (19) | 0.022 (2) | −0.0077 (19) |
C7 | 0.031 (2) | 0.054 (2) | 0.033 (2) | 0.0016 (18) | 0.0053 (17) | 0.0022 (17) |
C8 | 0.047 (2) | 0.043 (2) | 0.065 (3) | −0.0007 (18) | 0.023 (2) | −0.0063 (19) |
O1—N1 | 1.206 (5) | C2—H2 | 0.9300 |
O2—N1 | 1.224 (5) | C3—C4 | 1.362 (5) |
O3—C7 | 1.352 (4) | C4—C5 | 1.362 (5) |
O3—C6 | 1.389 (4) | C4—H4 | 0.9300 |
O4—C7 | 1.186 (4) | C5—C6 | 1.368 (5) |
N1—C3 | 1.458 (5) | C5—H5 | 0.9300 |
C1—C6 | 1.357 (5) | C7—C8 | 1.470 (5) |
C1—C2 | 1.369 (5) | C8—C8i | 1.488 (7) |
C1—H1 | 0.9300 | C8—H8A | 0.9700 |
C2—C3 | 1.371 (6) | C8—H8B | 0.9700 |
C7—O3—C6 | 120.1 (3) | C4—C5—C6 | 118.8 (4) |
O1—N1—O2 | 122.9 (5) | C4—C5—H5 | 120.6 |
O1—N1—C3 | 119.6 (5) | C6—C5—H5 | 120.6 |
O2—N1—C3 | 117.5 (5) | C1—C6—C5 | 122.5 (4) |
C6—C1—C2 | 118.7 (4) | C1—C6—O3 | 121.1 (4) |
C6—C1—H1 | 120.6 | C5—C6—O3 | 116.3 (4) |
C2—C1—H1 | 120.6 | O4—C7—O3 | 122.9 (3) |
C1—C2—C3 | 118.7 (4) | O4—C7—C8 | 127.4 (3) |
C1—C2—H2 | 120.6 | O3—C7—C8 | 109.7 (3) |
C3—C2—H2 | 120.6 | C7—C8—C8i | 113.5 (4) |
C4—C3—C2 | 122.2 (4) | C7—C8—H8A | 108.9 |
C4—C3—N1 | 119.3 (4) | C8i—C8—H8A | 108.9 |
C2—C3—N1 | 118.4 (4) | C7—C8—H8B | 108.9 |
C3—C4—C5 | 118.9 (4) | C8i—C8—H8B | 108.9 |
C3—C4—H4 | 120.5 | H8A—C8—H8B | 107.7 |
C5—C4—H4 | 120.5 | ||
C6—C1—C2—C3 | 0.6 (5) | C2—C1—C6—C5 | 0.1 (5) |
C1—C2—C3—C4 | −1.2 (6) | C2—C1—C6—O3 | 177.0 (3) |
C1—C2—C3—N1 | 177.1 (3) | C4—C5—C6—C1 | −0.2 (5) |
O1—N1—C3—C4 | −174.5 (4) | C4—C5—C6—O3 | −177.3 (3) |
O2—N1—C3—C4 | 5.2 (6) | C7—O3—C6—C1 | 69.0 (4) |
O1—N1—C3—C2 | 7.1 (6) | C7—O3—C6—C5 | −113.9 (4) |
O2—N1—C3—C2 | −173.1 (4) | C6—O3—C7—O4 | −1.9 (5) |
C2—C3—C4—C5 | 1.0 (5) | C6—O3—C7—C8 | 176.4 (3) |
N1—C3—C4—C5 | −177.2 (3) | O4—C7—C8—C8i | −7.3 (7) |
C3—C4—C5—C6 | −0.3 (5) | O3—C7—C8—C8i | 174.5 (4) |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H12N2O8 |
Mr | 360.28 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 13.539 (13), 9.049 (9), 14.662 (14) |
β (°) | 116.609 (15) |
V (Å3) | 1606 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.20 × 0.18 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3797, 1415, 698 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.196, 1.01 |
No. of reflections | 1415 |
No. of parameters | 118 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.26 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
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As part of our ongoing studies, we synthesized the title compound, (I), and report herein its synthesis and crystal structure.
In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). It is centrosymmetric. Ring A (C1—C6) is, of course, planar and the two symmetry related phenyl rings are coplanar. However in the similar structure, 1,4-Bis(3-pyridylaminomethyl)benzene (Zhu et al., 2007), the dihedral angle between the pyridyl ring and the central benzene ring is 63.6 (2)°.