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The asymmetric unit of the title compound, C13H8N2O7·1 \over 3 C6H6, contains three mol­ecules of the carbonate and one of benzene. The conformation of all carbonates is s-cis-s-cis, with some slight deviations from linearity. The aromatic rings subtend interplanar angles of 45-68° with the carbonate plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007499/bt6263sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007499/bt6263Isup2.hkl
Contains datablock I

CCDC reference: 214629

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.079
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

In the previous paper (Simon et al., 2003) we presented introductory material concerning diaryl carbonates, together with the structure of bis(o-nitrophenyl) carbonate. Here we present the structure of the isomeric bis(p-nitrophenyl) carbonate (I), which crystallizes from benzene as a solvate in which the asymmetric unit contains three molecules of (I) and one of benzene (Fig. 1). Atoms of the second and third independent molecules are distinguished by primes and double primes respectively.

The carbonate moieties all display the s-cis–s-cis conformation (cf. torsion angles in Table 1); the largest deviation of an ipso carbon from the carbonate plane (defined by the four atoms C1, O1; O2, O3) is 0.289 (2) Å for C21'. The aromatic rings are inclined to the carbonate plane at angles varying from 45 to 68° (for details see supplementary material).

Bond lengths and angles of the carbonate moieties (Table 1) may be considered normal, although the angle O2—C1—O3 is among the narrowest recorded for a diaryl carbonate.

There are eight short intramolecular contacts X···O (X = C,N,O) (see Supp. Mat.). The molecular packing also involves a series of C—H···O hydrogen bonds (Table 2). However, perhaps the most striking feature of the packing is the C104—H104···π contact involving the benzene ring and the centroid of C11'–C16', with normalized H···π 2.73 Å, angle 172°. This can be recognized in Fig. 1.

Experimental top

Triphosgene (bis(trichloromethyl) carbonate) was treated with six equivalents of p-nitrophenol and six equivalents of triethylamine in dichloromethane and recrystallized from benzene (Simon et al., 2001).

Refinement top

Hydrogen atoms were included using a riding model, with fixed C—H bond lengths of 0.95 Å; U(H) values were fixed at 1.2 times the U(eq) of the parent atom.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound in the crystal. Ellipsoids represent 50% probability levels; H atom radii are arbitrary.
Bis(p-nitrophenyl) carbonate benzene solvate (3:1) top
Crystal data top
C13H8N2O7·1/3C6H6F(000) = 2040
Mr = 330.25Dx = 1.531 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 21.074 (2) ÅCell parameters from 6133 reflections
b = 8.4949 (8) Åθ = 2.5–26.4°
c = 25.828 (2) ŵ = 0.12 mm1
β = 111.618 (5)°T = 133 K
V = 4298.6 (7) Å3Prism, colourless
Z = 120.40 × 0.25 × 0.15 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
5569 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 26.4°, θmin = 1.6°
Detector resolution: 8.192 pixels mm-1h = 2618
ω–scank = 1010
26129 measured reflectionsl = 3132
8781 independent reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0333P)2]
where P = (Fo2 + 2Fc2)/3
8781 reflections(Δ/σ)max < 0.001
649 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C13H8N2O7·1/3C6H6V = 4298.6 (7) Å3
Mr = 330.25Z = 12
Monoclinic, P21/cMo Kα radiation
a = 21.074 (2) ŵ = 0.12 mm1
b = 8.4949 (8) ÅT = 133 K
c = 25.828 (2) Å0.40 × 0.25 × 0.15 mm
β = 111.618 (5)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
5569 reflections with I > 2σ(I)
26129 measured reflectionsRint = 0.048
8781 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 0.92Δρmax = 0.24 e Å3
8781 reflectionsΔρmin = 0.21 e Å3
649 parameters
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)

15.0917 (0.0098) x + 5.5125 (0.0043) y − 0.6415 (0.0167) z = 1.0199 (0.0022)

* −0.0062 (0.0011) C11 * 0.0086 (0.0011) C12 * −0.0031 (0.0011) C13 * −0.0049 (0.0011) C14 * 0.0072 (0.0011) C15 * −0.0017 (0.0011) C16

Rms deviation of fitted atoms = 0.0058

− 21.0139 (0.0023) x + 0.5765 (0.0063) y + 8.6857 (0.0197) z = 1.5257 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 47.26 (0.05)

* 0.0032 (0.0014) C1 * −0.0013 (0.0006) O1 * −0.0009 (0.0004) O2 * −0.0009 (0.0004) O3 0.0180 (0.0026) C11 − 0.0096 (0.0027) C21

Rms deviation of fitted atoms = 0.0018

− 11.2215 (0.0120) x − 7.0549 (0.0032) y + 8.9956 (0.0161) z = 0.2280 (0.0055)

Angle to previous plane (with approximate e.s.d.) = 62.02 (0.05)

* −0.0039 (0.0012) C21 * 0.0012 (0.0012) C22 * 0.0024 (0.0011) C23 * −0.0034 (0.0011) C24 * 0.0008 (0.0011) C25 * 0.0029 (0.0011) C26

Rms deviation of fitted atoms = 0.0027

11.5111 (0.0113) x + 6.2091 (0.0038) y + 4.6268 (0.0157) z = 5.5388 (0.0028)

Angle to previous plane (with approximate e.s.d.) = 33.81 (0.06)

* 0.0044 (0.0011) C11' * −0.0007 (0.0011) C12' * −0.0022 (0.0011) C13' * 0.0014 (0.0011) C14' * 0.0023 (0.0011) C15' * −0.0052 (0.0011) C16'

Rms deviation of fitted atoms = 0.0031

15.1122 (0.0102) x − 1.2489 (0.0055) y + 9.5354 (0.0166) z = 6.3367 (0.0024)

Angle to previous plane (with approximate e.s.d.) = 55.74 (0.06)

* −0.0058 (0.0012) C1' * 0.0024 (0.0005) O1' * 0.0017 (0.0004) O2' * 0.0017 (0.0004) O3' −0.1276 (0.0023) C11' −0.2889 (0.0023) C21'

Rms deviation of fitted atoms = 0.0034

15.3857 (0.0097) x + 5.7806 (0.0042) y − 8.4561 (0.0163) z = 3.5730 (0.0053)

Angle to previous plane (with approximate e.s.d.) = 67.62 (0.05)

* 0.0028 (0.0012) C21' * −0.0102 (0.0012) C22' * 0.0085 (0.0012) C23' * 0.0006 (0.0011) C24' * −0.0080 (0.0011) C25' * 0.0064 (0.0011) C26'

Rms deviation of fitted atoms = 0.0069

15.0568 (0.0098) x − 5.3739 (0.0044) y + 0.3788 (0.0163) z = 0.0345 (0.0099)

Angle to previous plane (with approximate e.s.d.) = 85.85 (0.04)

* −0.0082 (0.0011) C11" * 0.0006 (0.0011) C12" * 0.0077 (0.0011) C13" * −0.0083 (0.0011) C14" * 0.0007 (0.0011) C15" * 0.0075 (0.0011) C16"

Rms deviation of fitted atoms = 0.0065

15.1477 (0.0111) x + 0.9976 (0.0057) y + 9.6144 (0.0183) z = 10.2386 (0.0068)

Angle to previous plane (with approximate e.s.d.) = 49.90 (0.06)

* −0.0004 (0.0013) C1" * 0.0002 (0.0005) O1" * 0.0001 (0.0004) O2" * 0.0001 (0.0004) O3" −0.1406 (0.0025) C11" −0.0667 (0.0025) C21"

Rms deviation of fitted atoms = 0.0002

11.7575 (0.0125) x + 6.5674 (0.0039) y + 1.9368 (0.0177) z = 10.4644 (0.0046)

Angle to previous plane (with approximate e.s.d.) = 45.69 (0.07)

* −0.0056 (0.0012) C21" * 0.0063 (0.0012) C22" * −0.0017 (0.0012) C23" * −0.0036 (0.0012) C24" * 0.0044 (0.0012) C25" * 0.0003 (0.0012) C26"

Rms deviation of fitted atoms = 0.0042

=============================================================================

Short contacts:

2.9230 (0.0017) O1 - O5_$2 3.0936 (0.0020) C23 - O3_$1 3.1182 (0.0019) C14" - O2'_$5 2.9838 (0.0016) O1" - O6' 2.9746 (0.0020) C1" - O6' 2.9502 (0.0021) C1 - O7'_$7 2.9348 (0.0018) N1' - O1"_$3 2.9966 (0.0019) C14' - O1"_$3

Operators for generating equivalent atoms:

$1 − x, y + 1/2, −z + 1/2 $2 − x, −y + 1, −z $3 x, −y + 1/2, z − 1/2 $5 x, −y + 1/2, z + 1/2 $7 − x, y − 1/2, −z + 1/2

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
O10.01126 (6)0.43743 (14)0.17370 (4)0.0320 (3)
O20.01704 (6)0.21654 (13)0.11996 (4)0.0320 (3)
O30.01845 (6)0.18862 (13)0.20765 (4)0.0350 (3)
O40.14343 (6)0.58296 (16)0.10593 (5)0.0436 (3)
O50.09830 (6)0.37969 (16)0.13037 (5)0.0385 (3)
O60.17613 (6)0.28928 (16)0.46195 (5)0.0430 (3)
O70.08190 (6)0.40695 (14)0.45328 (4)0.0347 (3)
N10.10969 (7)0.46043 (18)0.09516 (6)0.0313 (4)
N20.11840 (7)0.33479 (16)0.43380 (5)0.0280 (3)
C10.00484 (8)0.2997 (2)0.16784 (6)0.0258 (4)
C110.03708 (8)0.2934 (2)0.06854 (6)0.0258 (4)
C120.01313 (8)0.2261 (2)0.03039 (6)0.0275 (4)
H120.01900.14250.04120.033*
C130.03681 (8)0.2825 (2)0.02362 (6)0.0282 (4)
H130.02190.23720.05080.034*
C140.08247 (8)0.4056 (2)0.03718 (6)0.0250 (4)
C150.10567 (8)0.47574 (19)0.00097 (7)0.0277 (4)
H150.13660.56180.00960.033*
C160.08270 (8)0.4175 (2)0.05493 (7)0.0285 (4)
H160.09800.46210.08200.034*
C210.04328 (9)0.23554 (19)0.26363 (6)0.0264 (4)
C220.00376 (9)0.32455 (19)0.28470 (6)0.0282 (4)
H220.03960.36280.26090.034*
C230.02836 (8)0.35728 (19)0.34119 (6)0.0245 (4)
H230.00240.41820.35710.029*
C240.09143 (8)0.29926 (19)0.37372 (6)0.0227 (4)
C250.13096 (8)0.20884 (19)0.35259 (7)0.0274 (4)
H250.17420.17020.37630.033*
C260.10633 (8)0.17610 (19)0.29641 (7)0.0282 (4)
H260.13210.11410.28060.034*
O1'0.31915 (6)0.41828 (13)0.21378 (4)0.0290 (3)
O2'0.30928 (5)0.15569 (13)0.19496 (4)0.0270 (3)
O3'0.27625 (5)0.24280 (13)0.25871 (4)0.0267 (3)
O4'0.35203 (6)0.23626 (15)0.03075 (5)0.0401 (3)
O5'0.43904 (6)0.08886 (15)0.01379 (5)0.0374 (3)
O6'0.17954 (6)0.67527 (16)0.40989 (5)0.0455 (4)
O7'0.13530 (6)0.80252 (15)0.33249 (5)0.0375 (3)
N1'0.38770 (7)0.16378 (17)0.01101 (6)0.0284 (3)
N2'0.16889 (7)0.69312 (17)0.36028 (6)0.0296 (3)
C1'0.30326 (8)0.2885 (2)0.22110 (6)0.0238 (4)
C11'0.33048 (8)0.16869 (19)0.14950 (6)0.0229 (4)
C12'0.38290 (8)0.07014 (19)0.15021 (6)0.0259 (4)
H12'0.40540.00480.18150.031*
C13'0.40208 (8)0.06863 (19)0.10421 (6)0.0256 (4)
H13'0.43790.00230.10330.031*
C14'0.36786 (8)0.16573 (19)0.05981 (6)0.0234 (4)
C15'0.31525 (8)0.26386 (19)0.05919 (6)0.0252 (4)
H15'0.29280.32960.02800.030*
C16'0.29595 (8)0.26447 (19)0.10479 (6)0.0255 (4)
H16'0.25960.32960.10540.031*
C21'0.25144 (8)0.36392 (19)0.28341 (6)0.0233 (4)
C22'0.19810 (8)0.4556 (2)0.25056 (6)0.0273 (4)
H22'0.18000.44260.21130.033*
C23'0.17120 (8)0.5671 (2)0.27566 (6)0.0265 (4)
H23'0.13520.63440.25400.032*
C24'0.19815 (8)0.57807 (19)0.33311 (6)0.0231 (4)
C25'0.25104 (8)0.48442 (19)0.36632 (6)0.0247 (4)
H25'0.26800.49430.40570.030*
C26'0.27879 (8)0.37550 (19)0.34066 (6)0.0245 (4)
H26'0.31580.31040.36210.029*
O1"0.31636 (6)0.63824 (14)0.50029 (4)0.0301 (3)
O2"0.27915 (6)0.84461 (13)0.53749 (5)0.0320 (3)
O3"0.31697 (6)0.89297 (14)0.47288 (5)0.0353 (3)
O4"0.18185 (6)0.57290 (15)0.72046 (5)0.0412 (3)
O5"0.12995 (8)0.41327 (19)0.65337 (6)0.0663 (5)
O6"0.45710 (7)0.67693 (18)0.30858 (5)0.0516 (4)
O7"0.38378 (6)0.84417 (17)0.25708 (5)0.0465 (4)
N1"0.16855 (7)0.52355 (18)0.67289 (6)0.0349 (4)
N2"0.41070 (7)0.77117 (19)0.30076 (6)0.0346 (4)
C1"0.30549 (8)0.7740 (2)0.50326 (6)0.0268 (4)
C11"0.25493 (8)0.74961 (19)0.57088 (6)0.0253 (4)
C12"0.21139 (8)0.62449 (19)0.54934 (7)0.0263 (4)
H12"0.20060.59150.51190.032*
C13"0.18381 (8)0.5483 (2)0.58343 (6)0.0275 (4)
H13"0.15410.46110.56990.033*
C14"0.20021 (8)0.6010 (2)0.63766 (6)0.0252 (4)
C15"0.24444 (8)0.7248 (2)0.65927 (6)0.0273 (4)
H15"0.25540.75770.69670.033*
C16"0.27246 (8)0.7997 (2)0.62543 (7)0.0271 (4)
H16"0.30340.88460.63930.033*
C21"0.34171 (9)0.8537 (2)0.43104 (7)0.0287 (4)
C22"0.39658 (8)0.7546 (2)0.44003 (7)0.0304 (4)
H22"0.41880.70650.47530.036*
C23"0.41870 (8)0.7266 (2)0.39659 (7)0.0294 (4)
H23"0.45600.65780.40140.035*
C24"0.38581 (8)0.8000 (2)0.34625 (6)0.0277 (4)
C25"0.33165 (8)0.9009 (2)0.33709 (7)0.0321 (4)
H25"0.31030.95080.30200.038*
C26"0.30923 (9)0.9276 (2)0.38034 (7)0.0336 (4)
H26"0.27180.99630.37530.040*
C1010.54435 (10)0.7894 (3)0.15648 (10)0.0505 (6)
H1010.57510.87590.16550.061*
C1020.52781 (11)0.7168 (3)0.10570 (9)0.0599 (7)
H1020.54670.75250.07960.072*
C1030.48244 (12)0.5885 (3)0.09310 (8)0.0622 (7)
H1030.47010.53580.05830.075*
C1040.45609 (10)0.5406 (3)0.13232 (9)0.0529 (6)
H1040.42540.45410.12460.063*
C1050.47393 (10)0.6171 (3)0.18192 (8)0.0481 (5)
H1050.45540.58360.20850.058*
C1060.51753 (10)0.7397 (3)0.19376 (8)0.0468 (5)
H1060.52950.79160.22860.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0418 (7)0.0239 (7)0.0275 (6)0.0076 (5)0.0096 (5)0.0001 (5)
O20.0524 (8)0.0235 (7)0.0180 (6)0.0016 (6)0.0104 (5)0.0005 (5)
O30.0619 (8)0.0221 (7)0.0187 (6)0.0002 (6)0.0121 (6)0.0000 (5)
O40.0458 (8)0.0417 (9)0.0338 (7)0.0040 (7)0.0035 (6)0.0119 (6)
O50.0380 (8)0.0548 (9)0.0237 (6)0.0049 (6)0.0126 (6)0.0011 (6)
O60.0341 (8)0.0526 (9)0.0294 (7)0.0066 (6)0.0034 (6)0.0007 (6)
O70.0400 (7)0.0396 (8)0.0254 (6)0.0012 (6)0.0131 (6)0.0061 (6)
N10.0247 (8)0.0380 (10)0.0266 (8)0.0071 (7)0.0041 (6)0.0061 (7)
N20.0310 (9)0.0246 (8)0.0254 (8)0.0051 (7)0.0067 (7)0.0003 (6)
C10.0305 (10)0.0254 (10)0.0220 (9)0.0013 (8)0.0104 (7)0.0012 (7)
C110.0309 (10)0.0250 (10)0.0203 (8)0.0047 (7)0.0079 (7)0.0024 (7)
C120.0267 (10)0.0295 (10)0.0252 (9)0.0013 (7)0.0084 (7)0.0015 (7)
C130.0255 (9)0.0351 (11)0.0244 (9)0.0032 (8)0.0096 (7)0.0012 (8)
C140.0225 (9)0.0298 (10)0.0198 (8)0.0082 (7)0.0043 (7)0.0042 (7)
C150.0284 (10)0.0223 (9)0.0291 (9)0.0019 (7)0.0068 (7)0.0027 (7)
C160.0350 (10)0.0255 (10)0.0274 (9)0.0025 (8)0.0142 (8)0.0033 (7)
C210.0400 (10)0.0190 (9)0.0193 (8)0.0043 (8)0.0100 (7)0.0001 (7)
C220.0317 (10)0.0242 (10)0.0231 (9)0.0011 (8)0.0038 (7)0.0005 (7)
C230.0291 (10)0.0207 (9)0.0250 (9)0.0005 (7)0.0114 (7)0.0025 (7)
C240.0256 (9)0.0216 (9)0.0195 (8)0.0056 (7)0.0067 (7)0.0006 (7)
C250.0264 (9)0.0259 (10)0.0294 (9)0.0001 (7)0.0097 (7)0.0043 (8)
C260.0362 (11)0.0218 (10)0.0311 (10)0.0005 (8)0.0177 (8)0.0005 (7)
O1'0.0407 (7)0.0232 (7)0.0267 (6)0.0017 (5)0.0165 (5)0.0006 (5)
O2'0.0389 (7)0.0216 (7)0.0269 (6)0.0004 (5)0.0195 (5)0.0010 (5)
O3'0.0385 (7)0.0229 (7)0.0238 (6)0.0036 (5)0.0173 (5)0.0026 (5)
O4'0.0529 (8)0.0459 (8)0.0222 (6)0.0020 (7)0.0146 (6)0.0027 (6)
O5'0.0311 (7)0.0510 (9)0.0353 (7)0.0024 (6)0.0184 (6)0.0068 (6)
O6'0.0547 (9)0.0611 (10)0.0214 (7)0.0259 (7)0.0149 (6)0.0018 (6)
O7'0.0447 (8)0.0331 (8)0.0351 (7)0.0173 (6)0.0150 (6)0.0072 (6)
N1'0.0315 (9)0.0306 (9)0.0239 (8)0.0102 (7)0.0111 (7)0.0071 (7)
N2'0.0279 (8)0.0328 (9)0.0267 (8)0.0066 (7)0.0082 (6)0.0011 (7)
C1'0.0261 (9)0.0240 (10)0.0204 (8)0.0028 (7)0.0074 (7)0.0010 (7)
C11'0.0265 (9)0.0225 (9)0.0217 (8)0.0044 (7)0.0112 (7)0.0032 (7)
C12'0.0280 (10)0.0257 (10)0.0229 (9)0.0016 (7)0.0080 (7)0.0018 (7)
C13'0.0229 (9)0.0276 (10)0.0266 (9)0.0008 (7)0.0096 (7)0.0037 (7)
C14'0.0264 (9)0.0259 (10)0.0181 (8)0.0071 (7)0.0085 (7)0.0055 (7)
C15'0.0274 (9)0.0249 (10)0.0196 (8)0.0031 (7)0.0044 (7)0.0002 (7)
C16'0.0252 (9)0.0244 (10)0.0262 (9)0.0009 (7)0.0089 (7)0.0025 (7)
C21'0.0288 (9)0.0211 (9)0.0234 (9)0.0004 (7)0.0136 (7)0.0000 (7)
C22'0.0327 (10)0.0315 (10)0.0164 (8)0.0026 (8)0.0075 (7)0.0018 (7)
C23'0.0263 (9)0.0274 (10)0.0231 (9)0.0048 (7)0.0061 (7)0.0053 (7)
C24'0.0257 (9)0.0223 (9)0.0230 (8)0.0024 (7)0.0109 (7)0.0003 (7)
C25'0.0249 (9)0.0293 (10)0.0186 (8)0.0001 (7)0.0065 (7)0.0006 (7)
C26'0.0233 (9)0.0266 (10)0.0234 (9)0.0028 (7)0.0083 (7)0.0041 (7)
O1"0.0382 (7)0.0232 (7)0.0322 (7)0.0054 (5)0.0168 (5)0.0023 (5)
O2"0.0466 (8)0.0241 (7)0.0322 (7)0.0017 (6)0.0226 (6)0.0017 (5)
O3"0.0540 (8)0.0245 (7)0.0375 (7)0.0018 (6)0.0287 (6)0.0033 (5)
O4"0.0574 (9)0.0433 (8)0.0301 (7)0.0020 (6)0.0246 (6)0.0028 (6)
O5"0.0847 (12)0.0687 (11)0.0602 (10)0.0484 (9)0.0439 (8)0.0243 (8)
O6"0.0512 (9)0.0710 (11)0.0388 (8)0.0287 (8)0.0241 (7)0.0130 (7)
O7"0.0479 (8)0.0647 (10)0.0279 (7)0.0105 (7)0.0152 (6)0.0171 (7)
N1"0.0399 (9)0.0343 (10)0.0353 (9)0.0014 (7)0.0194 (7)0.0016 (7)
N2"0.0317 (9)0.0447 (10)0.0269 (8)0.0014 (8)0.0100 (7)0.0050 (7)
C1"0.0314 (10)0.0262 (11)0.0242 (9)0.0004 (8)0.0118 (7)0.0009 (7)
C11"0.0286 (10)0.0224 (9)0.0272 (9)0.0028 (7)0.0132 (7)0.0032 (7)
C12"0.0291 (10)0.0278 (10)0.0210 (8)0.0016 (7)0.0080 (7)0.0030 (7)
C13"0.0265 (10)0.0251 (10)0.0300 (9)0.0008 (7)0.0095 (7)0.0029 (7)
C14"0.0255 (9)0.0258 (10)0.0261 (9)0.0037 (7)0.0117 (7)0.0017 (7)
C15"0.0287 (10)0.0294 (10)0.0226 (9)0.0034 (8)0.0082 (7)0.0035 (7)
C16"0.0287 (10)0.0242 (10)0.0280 (9)0.0006 (7)0.0100 (7)0.0043 (7)
C21"0.0360 (10)0.0241 (10)0.0301 (10)0.0031 (8)0.0171 (8)0.0008 (7)
C22"0.0319 (10)0.0335 (11)0.0241 (9)0.0008 (8)0.0085 (7)0.0063 (8)
C23"0.0245 (9)0.0342 (11)0.0284 (9)0.0044 (8)0.0086 (7)0.0060 (8)
C24"0.0275 (10)0.0319 (11)0.0241 (9)0.0019 (8)0.0099 (7)0.0039 (8)
C25"0.0336 (11)0.0326 (11)0.0280 (9)0.0040 (8)0.0091 (8)0.0104 (8)
C26"0.0372 (11)0.0270 (10)0.0398 (11)0.0070 (8)0.0180 (9)0.0085 (8)
C1010.0327 (12)0.0405 (13)0.0730 (16)0.0020 (9)0.0133 (11)0.0090 (11)
C1020.0440 (14)0.088 (2)0.0604 (15)0.0294 (13)0.0336 (12)0.0364 (14)
C1030.0566 (15)0.086 (2)0.0345 (12)0.0293 (14)0.0051 (11)0.0169 (12)
C1040.0413 (13)0.0463 (14)0.0660 (15)0.0086 (10)0.0139 (11)0.0146 (12)
C1050.0501 (13)0.0504 (14)0.0496 (13)0.0012 (11)0.0250 (10)0.0032 (11)
C1060.0404 (12)0.0475 (14)0.0451 (12)0.0060 (10)0.0072 (10)0.0069 (10)
Geometric parameters (Å, º) top
O1—C11.1809 (19)C21'—C26'1.379 (2)
O2—C11.3494 (19)C22'—C23'1.382 (2)
O2—C111.3981 (18)C22'—H22'0.9500
O3—C11.3466 (19)C23'—C24'1.383 (2)
O3—C211.4019 (18)C23'—H23'0.9500
O4—N11.2332 (18)C24'—C25'1.381 (2)
O5—N11.2311 (18)C25'—C26'1.387 (2)
O6—N21.2275 (16)C25'—H25'0.9500
O7—N21.2271 (17)C26'—H26'0.9500
N1—C141.468 (2)O1"—C1"1.1839 (19)
N2—C241.4738 (19)O2"—C1"1.3458 (19)
C11—C161.382 (2)O2"—C11"1.4070 (19)
C11—C121.385 (2)O3"—C1"1.355 (2)
C12—C131.383 (2)O3"—C21"1.4024 (19)
C12—H120.9500O4"—N1"1.2288 (17)
C13—C141.376 (2)O5"—N1"1.2212 (18)
C13—H130.9500O6"—N2"1.2216 (18)
C14—C151.386 (2)O7"—N2"1.2279 (17)
C15—C161.387 (2)N1"—C14"1.468 (2)
C15—H150.9500N2"—C24"1.473 (2)
C16—H160.9500C11"—C12"1.380 (2)
C21—C221.377 (2)C11"—C16"1.385 (2)
C21—C261.381 (2)C12"—C13"1.382 (2)
C22—C231.385 (2)C12"—H12"0.9500
C22—H220.9500C13"—C14"1.387 (2)
C23—C241.376 (2)C13"—H13"0.9500
C23—H230.9500C14"—C15"1.380 (2)
C24—C251.385 (2)C15"—C16"1.377 (2)
C25—C261.377 (2)C15"—H15"0.9500
C25—H250.9500C16"—H16"0.9500
C26—H260.9500C21"—C22"1.379 (2)
O1'—C1'1.1872 (19)C21"—C26"1.385 (2)
O2'—C1'1.3448 (19)C22"—C23"1.385 (2)
O2'—C11'1.4061 (18)C22"—H22"0.9500
O3'—C1'1.3514 (19)C23"—C24"1.377 (2)
O3'—C21'1.4087 (18)C23"—H23"0.9500
O4'—N1'1.2288 (17)C24"—C25"1.376 (2)
O5'—N1'1.2344 (17)C25"—C26"1.383 (2)
O6'—N2'1.2263 (16)C25"—H25"0.9500
O7'—N2'1.2269 (16)C26"—H26"0.9500
N1'—C14'1.467 (2)C101—C1061.351 (3)
N2'—C24'1.465 (2)C101—C1021.373 (3)
C11'—C16'1.381 (2)C101—H1010.9500
C11'—C12'1.381 (2)C102—C1031.407 (3)
C12'—C13'1.389 (2)C102—H1020.9500
C12'—H12'0.9500C103—C1041.384 (3)
C13'—C14'1.381 (2)C103—H1030.9500
C13'—H13'0.9500C104—C1051.360 (3)
C14'—C15'1.382 (2)C104—H1040.9500
C15'—C16'1.380 (2)C105—C1061.347 (3)
C15'—H15'0.9500C105—H1050.9500
C16'—H16'0.9500C106—H1060.9500
C21'—C22'1.374 (2)
C1—O2—C11120.50 (13)C21'—C22'—H22'120.6
C1—O3—C21118.81 (13)C23'—C22'—H22'120.6
O5—N1—O4123.82 (14)C22'—C23'—C24'118.17 (15)
O5—N1—C14117.86 (15)C22'—C23'—H23'120.9
O4—N1—C14118.31 (15)C24'—C23'—H23'120.9
O7—N2—O6123.28 (13)C25'—C24'—C23'123.11 (15)
O7—N2—C24118.50 (13)C25'—C24'—N2'118.21 (13)
O6—N2—C24118.22 (14)C23'—C24'—N2'118.68 (14)
O1—C1—O3127.89 (15)C24'—C25'—C26'118.28 (14)
O1—C1—O2128.36 (15)C24'—C25'—H25'120.9
O3—C1—O2103.74 (14)C26'—C25'—H25'120.9
C16—C11—C12122.38 (15)C21'—C26'—C25'118.49 (15)
C16—C11—O2122.42 (15)C21'—C26'—H26'120.8
C12—C11—O2114.91 (15)C25'—C26'—H26'120.8
C13—C12—C11118.94 (16)C1"—O2"—C11"118.53 (13)
C13—C12—H12120.5C1"—O3"—C21"117.72 (13)
C11—C12—H12120.5O5"—N1"—O4"123.12 (15)
C14—C13—C12118.62 (16)O5"—N1"—C14"118.28 (14)
C14—C13—H13120.7O4"—N1"—C14"118.60 (15)
C12—C13—H13120.7O6"—N2"—O7"123.62 (15)
C13—C14—C15122.86 (15)O6"—N2"—C24"118.40 (14)
C13—C14—N1118.33 (15)O7"—N2"—C24"117.99 (15)
C15—C14—N1118.76 (16)O1"—C1"—O2"127.82 (16)
C14—C15—C16118.50 (16)O1"—C1"—O3"127.52 (16)
C14—C15—H15120.7O2"—C1"—O3"104.66 (14)
C16—C15—H15120.7C12"—C11"—C16"122.34 (15)
C11—C16—C15118.69 (16)C12"—C11"—O2"122.14 (14)
C11—C16—H16120.7C16"—C11"—O2"115.23 (15)
C15—C16—H16120.7C11"—C12"—C13"118.50 (15)
C22—C21—C26122.93 (14)C11"—C12"—H12"120.8
C22—C21—O3120.89 (15)C13"—C12"—H12"120.8
C26—C21—O3115.95 (15)C12"—C13"—C14"119.02 (16)
C21—C22—C23118.72 (15)C12"—C13"—H13"120.5
C21—C22—H22120.6C14"—C13"—H13"120.5
C23—C22—H22120.6C15"—C14"—C13"122.31 (16)
C24—C23—C22118.29 (15)C15"—C14"—N1"119.00 (15)
C24—C23—H23120.9C13"—C14"—N1"118.69 (15)
C22—C23—H23120.9C16"—C15"—C14"118.61 (15)
C23—C24—C25122.98 (14)C16"—C15"—H15"120.7
C23—C24—N2118.73 (14)C14"—C15"—H15"120.7
C25—C24—N2118.29 (14)C15"—C16"—C11"119.19 (16)
C26—C25—C24118.64 (15)C15"—C16"—H16"120.4
C26—C25—H25120.7C11"—C16"—H16"120.4
C24—C25—H25120.7C22"—C21"—C26"121.88 (16)
C25—C26—C21118.43 (15)C22"—C21"—O3"122.83 (14)
C25—C26—H26120.8C26"—C21"—O3"115.22 (15)
C21—C26—H26120.8C21"—C22"—C23"118.68 (15)
C1'—O2'—C11'118.11 (12)C21"—C22"—H22"120.7
C1'—O3'—C21'116.13 (12)C23"—C22"—H22"120.7
O4'—N1'—O5'123.30 (14)C24"—C23"—C22"118.99 (16)
O4'—N1'—C14'118.20 (14)C24"—C23"—H23"120.5
O5'—N1'—C14'118.49 (13)C22"—C23"—H23"120.5
O6'—N2'—O7'123.29 (14)C25"—C24"—C23"122.78 (16)
O6'—N2'—C24'118.08 (13)C25"—C24"—N2"118.87 (14)
O7'—N2'—C24'118.63 (13)C23"—C24"—N2"118.34 (15)
O1'—C1'—O2'127.94 (15)C24"—C25"—C26"118.17 (15)
O1'—C1'—O3'126.85 (15)C24"—C25"—H25"120.9
O2'—C1'—O3'105.20 (13)C26"—C25"—H25"120.9
C16'—C11'—C12'122.75 (15)C25"—C26"—C21"119.49 (16)
C16'—C11'—O2'120.87 (14)C25"—C26"—H26"120.3
C12'—C11'—O2'116.11 (13)C21"—C26"—H26"120.3
C11'—C12'—C13'118.54 (15)C106—C101—C102121.0 (2)
C11'—C12'—H12'120.7C106—C101—H101119.5
C13'—C12'—H12'120.7C102—C101—H101119.5
C14'—C13'—C12'118.52 (15)C101—C102—C103118.7 (2)
C14'—C13'—H13'120.7C101—C102—H102120.6
C12'—C13'—H13'120.7C103—C102—H102120.6
C13'—C14'—C15'122.76 (15)C104—C103—C102118.7 (2)
C13'—C14'—N1'118.68 (15)C104—C103—H103120.6
C15'—C14'—N1'118.57 (14)C102—C103—H103120.6
C16'—C15'—C14'118.66 (14)C105—C104—C103120.2 (2)
C16'—C15'—H15'120.7C105—C104—H104119.9
C14'—C15'—H15'120.7C103—C104—H104119.9
C15'—C16'—C11'118.77 (15)C106—C105—C104120.8 (2)
C15'—C16'—H16'120.6C106—C105—H105119.6
C11'—C16'—H16'120.6C104—C105—H105119.6
C22'—C21'—C26'123.06 (15)C105—C106—C101120.6 (2)
C22'—C21'—O3'119.35 (13)C105—C106—H106119.7
C26'—C21'—O3'117.36 (14)C101—C106—H106119.7
C21'—C22'—C23'118.87 (14)
C21—O3—C1—O10.1 (3)C1'—O3'—C21'—C26'122.45 (15)
C21—O3—C1—O2179.47 (13)C26'—C21'—C22'—C23'1.4 (3)
C11—O2—C1—O11.4 (3)O3'—C21'—C22'—C23'175.75 (14)
C11—O2—C1—O3179.22 (13)C21'—C22'—C23'—C24'1.8 (2)
C1—O2—C11—C1650.0 (2)C22'—C23'—C24'—C25'0.8 (3)
C1—O2—C11—C12136.11 (15)C22'—C23'—C24'—N2'178.46 (15)
C16—C11—C12—C131.5 (2)O6'—N2'—C24'—C25'18.3 (2)
O2—C11—C12—C13172.42 (14)O7'—N2'—C24'—C25'161.38 (15)
C11—C12—C13—C141.1 (2)O6'—N2'—C24'—C23'161.01 (15)
C12—C13—C14—C150.1 (2)O7'—N2'—C24'—C23'19.3 (2)
C12—C13—C14—N1177.39 (14)C23'—C24'—C25'—C26'0.7 (3)
O5—N1—C14—C1310.4 (2)N2'—C24'—C25'—C26'179.99 (14)
O4—N1—C14—C13170.71 (15)C22'—C21'—C26'—C25'0.2 (3)
O5—N1—C14—C15167.23 (14)O3'—C21'—C26'—C25'174.29 (14)
O4—N1—C14—C1511.7 (2)C24'—C25'—C26'—C21'1.2 (2)
C13—C14—C15—C161.1 (2)C11"—O2"—C1"—O1"6.6 (2)
N1—C14—C15—C16176.41 (14)C11"—O2"—C1"—O3"173.48 (12)
C12—C11—C16—C150.5 (2)C21"—O3"—C1"—O1"3.1 (2)
O2—C11—C16—C15172.94 (14)C21"—O3"—C1"—O2"176.93 (13)
C14—C15—C16—C110.8 (2)C1"—O2"—C11"—C12"49.0 (2)
C1—O3—C21—C2264.8 (2)C1"—O2"—C11"—C16"137.01 (15)
C1—O3—C21—C26120.47 (16)C16"—C11"—C12"—C13"0.9 (2)
C26—C21—C22—C230.5 (3)O2"—C11"—C12"—C13"172.72 (14)
O3—C21—C22—C23174.87 (14)C11"—C12"—C13"—C14"0.7 (2)
C21—C22—C23—C240.1 (2)C12"—C13"—C14"—C15"1.6 (2)
C22—C23—C24—C250.6 (2)C12"—C13"—C14"—N1"177.57 (14)
C22—C23—C24—N2179.38 (14)O5"—N1"—C14"—C15"179.38 (17)
O7—N2—C24—C234.3 (2)O4"—N1"—C14"—C15"0.9 (2)
O6—N2—C24—C23176.37 (15)O5"—N1"—C14"—C13"1.5 (2)
O7—N2—C24—C25175.77 (15)O4"—N1"—C14"—C13"178.25 (15)
O6—N2—C24—C253.6 (2)C13"—C14"—C15"—C16"0.9 (2)
C23—C24—C25—C260.4 (2)N1"—C14"—C15"—C16"178.23 (14)
N2—C24—C25—C26179.53 (14)C14"—C15"—C16"—C11"0.6 (2)
C24—C25—C26—C210.2 (2)C12"—C11"—C16"—C15"1.5 (2)
C22—C21—C26—C250.7 (3)O2"—C11"—C16"—C15"172.47 (14)
O3—C21—C26—C25175.28 (14)C1"—O3"—C21"—C22"49.0 (2)
C11'—O2'—C1'—O1'6.9 (2)C1"—O3"—C21"—C26"134.02 (16)
C11'—O2'—C1'—O3'174.26 (12)C26"—C21"—C22"—C23"1.2 (3)
C21'—O3'—C1'—O1'14.2 (2)O3"—C21"—C22"—C23"177.98 (15)
C21'—O3'—C1'—O2'166.98 (11)C21"—C22"—C23"—C24"0.8 (3)
C1'—O2'—C11'—C16'54.98 (19)C22"—C23"—C24"—C25"0.1 (3)
C1'—O2'—C11'—C12'130.82 (15)C22"—C23"—C24"—N2"178.95 (15)
C16'—C11'—C12'—C13'0.7 (2)O6"—N2"—C24"—C25"177.28 (17)
O2'—C11'—C12'—C13'174.75 (13)O7"—N2"—C24"—C25"3.1 (2)
C11'—C12'—C13'—C14'0.0 (2)O6"—N2"—C24"—C23"3.8 (2)
C12'—C13'—C14'—C15'0.2 (2)O7"—N2"—C24"—C23"175.76 (16)
C12'—C13'—C14'—N1'179.65 (13)C23"—C24"—C25"—C26"0.7 (3)
O4'—N1'—C14'—C13'171.67 (14)N2"—C24"—C25"—C26"179.52 (15)
O5'—N1'—C14'—C13'7.9 (2)C24"—C25"—C26"—C21"0.3 (3)
O4'—N1'—C14'—C15'7.8 (2)C22"—C21"—C26"—C25"0.7 (3)
O5'—N1'—C14'—C15'172.61 (14)O3"—C21"—C26"—C25"177.64 (15)
C13'—C14'—C15'—C16'0.2 (2)C106—C101—C102—C1030.3 (3)
N1'—C14'—C15'—C16'179.23 (13)C101—C102—C103—C1040.1 (3)
C14'—C15'—C16'—C11'0.8 (2)C102—C103—C104—C1050.1 (3)
C12'—C11'—C16'—C15'1.1 (2)C103—C104—C105—C1060.2 (3)
O2'—C11'—C16'—C15'174.90 (13)C104—C105—C106—C1010.1 (3)
C1'—O3'—C21'—C22'62.84 (19)C102—C101—C106—C1050.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O2i0.952.603.249 (2)126
C16—H16···O4ii0.952.563.476 (2)161
C22—H22···O4ii0.952.553.495 (2)174
C22—H22···O5ii0.952.643.3478 (19)132
C15—H15···O6i0.952.593.356 (2)138
C13—H13···O7iii0.952.473.210 (2)134
C16"—H16"···O1iv0.952.483.203 (2)133
C26—H26···O4v0.952.623.2461 (19)124
C22"—H22"···O5v0.952.673.418 (2)136
C23"—H23"···O5vi0.952.543.256 (2)132
C12"—H12"···O60.952.603.439 (2)147
C22—H22···O7vii0.952.563.3540 (19)141
C25—H25···O1"0.952.583.4736 (19)157
C12—H12···O7"viii0.952.563.357 (2)142
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+1/2, z1/2; (iv) x, y+3/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x+1, y+1/2, z+1/2; (vii) x, y1/2, z+1/2; (viii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC13H8N2O7·1/3C6H6
Mr330.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)133
a, b, c (Å)21.074 (2), 8.4949 (8), 25.828 (2)
β (°) 111.618 (5)
V3)4298.6 (7)
Z12
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.40 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
26129, 8781, 5569
Rint0.048
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.079, 0.92
No. of reflections8781
No. of parameters649
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C11.1809 (19)O3'—C1'1.3514 (19)
O2—C11.3494 (19)O3'—C21'1.4087 (18)
O2—C111.3981 (18)O1"—C1"1.1839 (19)
O3—C11.3466 (19)O2"—C1"1.3458 (19)
O3—C211.4019 (18)O2"—C11"1.4070 (19)
O1'—C1'1.1872 (19)O3"—C1"1.355 (2)
O2'—C1'1.3448 (19)O3"—C21"1.4024 (19)
O2'—C11'1.4061 (18)
O1—C1—O3127.89 (15)O2'—C1'—O3'105.20 (13)
O1—C1—O2128.36 (15)O1"—C1"—O2"127.82 (16)
O3—C1—O2103.74 (14)O1"—C1"—O3"127.52 (16)
O1'—C1'—O2'127.94 (15)O2"—C1"—O3"104.66 (14)
O1'—C1'—O3'126.85 (15)
C21—O3—C1—O10.1 (3)C21'—O3'—C1'—O1'14.2 (2)
C11—O2—C1—O11.4 (3)C11"—O2"—C1"—O1"6.6 (2)
C11'—O2'—C1'—O1'6.9 (2)C21"—O3"—C1"—O1"3.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O2i0.952.603.249 (2)126.3
C16'—H16'···O4ii0.952.563.476 (2)161.2
C22'—H22'···O4ii0.952.553.495 (2)174.1
C22'—H22'···O5ii0.952.643.3478 (19)131.9
C15—H15···O6i0.952.593.356 (2)138.2
C13—H13···O7iii0.952.473.210 (2)134.2
C16"—H16"···O1'iv0.952.483.203 (2)133.1
C26'—H26'···O4'v0.952.623.2461 (19)124.1
C22"—H22"···O5'v0.952.673.418 (2)135.6
C23"—H23"···O5'vi0.952.543.256 (2)132.1
C12"—H12"···O6'0.952.603.439 (2)146.8
C22—H22···O7'vii0.952.563.3540 (19)140.9
C25'—H25'···O1"0.952.583.4736 (19)156.5
C12'—H12'···O7"viii0.952.563.357 (2)142.0
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+1/2, z1/2; (iv) x, y+3/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x+1, y+1/2, z+1/2; (vii) x, y1/2, z+1/2; (viii) x, y1, z.
 

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