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The title compound, C14H10N4O10, was obtained by nitration of 6,6′-dimeth­oxy-2,2′-dinitro-1,1′-biphenyl in the presence of an excess of fuming nitric acid. In the mol­ecule, the dihedral angle between the two benzene rings is 89.9 (2)°. In the crystal structure, mol­ecules are connected by weak inter­molecular C—H...O hydrogen bonds to form one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040202/lh2441sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040202/lh2441Isup2.hkl
Contains datablock I

CCDC reference: 663729

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.135
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 48
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

Comment top

Nitro compounds, specifically aromatic nitro compounds have been widely studied owing to their potential application in e.g. pathology (Ramkishen et al., 2005), materials science (Shinichi & Yuichiro, 2005) and powder technology (Zhang, 2006). These compounds can also be reduced to obtain hydroxylamine, azo-, azoxy compounds and amines, which find applications in dyes, agrochemicals, pharmaceuticals and photographic chemicals (Agrawal & Tratnyek, 1996). In this paper, we report the synthesis and crystal structure of the title compound.

All bond lengths and angles in the title molecule (Fig. 1) are in the expected range (Unver et al., 2002) and in good agreement with those reported previously (Yang et al., 2005). Atoms N1/N2/O1/C1—C6/C14 lie in a plane with the largest deviation being 0.029 Å for atom N2, and atoms N3/N4/O10/C7—C12 also lie in a plane, with the largest deviation being 0.0354 Å for atom N4. The dihedral angle between the two benzene rings is 90.1°, which is considerably larger than found in other biphenyls (Fischer et al., 2007), possibly due to the concomitant effects of steric hindrance of the methoxy and nitro groups. The dihedral angles formed between the benzene ring of C1—C6 and planes N1/O2/O3 and N2/O4/O5 are 24.3 and 70.4°, the dihedral angles formed between the benzene ring of C7—C12 and planes N3/O6/O7 and N4/O8/O9 are 15.7 and 43.0°, respectively. The H atom of the methoxy group forms weak C—H···O intermolecular hydrogen bonds with the nitro group O atom of the neighbouring molecule. The H13B···O5i distance is 2.41 Å, which is considerable shorter than the sum of the van der Waals radii for O and H (2.70 Å). In the crystal structure, molecules are connected to form a one-dimension chain via weak C—H···O hydrogen bonds. In addition, there are also weak C—H···O hydrogen bonds between two one-dimension chains (Fig.2). The H14A···O6ii distance is 2.60 Å. These weak intermolecular C—H···O hydrogen bonds play an important role in stabilizing the crystal structure (symmetry operation: (i) 1 + x,y,z; (ii) 1 - x,1 - y,1 - z).

Related literature top

For related literature, see: Agrawal & Tratnyek (1996); Fischer et al. (2007); Chen et al. (2001); Ramkishen et al. (2005); Shinichi & Yuichiro (2005); Unver et al. (2002); Yang et al. (2005); Zhang (2006).

Experimental top

6,6'-Dimethoxy-2,2'-dinitro-1,1'-biphenyl was prepared according to the reported procedure (Chen et al., 2001). The title compound was synthesized by the nitration reaction of 6,6'-Dimethoxy-2,2'-dinitro-1,1'-biphenyl (0.5 mmol) in 20 ml fuming nitric acid at room temperature for 24 h. The resulting solution was poured into 50 ml ice water and the precipitation was collected by filtration and recrystallized from ethyl acetate as single crystals of the title compound, which were suitable for X-ray diffraction analysis.

Refinement top

All H atoms were placed in calculated positions with C—H distances 0.93–0.96 Å and included in the refinement in the riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. Atoms O2—O9 were loosely restrained to be approximately isotropic.

Structure description top

Nitro compounds, specifically aromatic nitro compounds have been widely studied owing to their potential application in e.g. pathology (Ramkishen et al., 2005), materials science (Shinichi & Yuichiro, 2005) and powder technology (Zhang, 2006). These compounds can also be reduced to obtain hydroxylamine, azo-, azoxy compounds and amines, which find applications in dyes, agrochemicals, pharmaceuticals and photographic chemicals (Agrawal & Tratnyek, 1996). In this paper, we report the synthesis and crystal structure of the title compound.

All bond lengths and angles in the title molecule (Fig. 1) are in the expected range (Unver et al., 2002) and in good agreement with those reported previously (Yang et al., 2005). Atoms N1/N2/O1/C1—C6/C14 lie in a plane with the largest deviation being 0.029 Å for atom N2, and atoms N3/N4/O10/C7—C12 also lie in a plane, with the largest deviation being 0.0354 Å for atom N4. The dihedral angle between the two benzene rings is 90.1°, which is considerably larger than found in other biphenyls (Fischer et al., 2007), possibly due to the concomitant effects of steric hindrance of the methoxy and nitro groups. The dihedral angles formed between the benzene ring of C1—C6 and planes N1/O2/O3 and N2/O4/O5 are 24.3 and 70.4°, the dihedral angles formed between the benzene ring of C7—C12 and planes N3/O6/O7 and N4/O8/O9 are 15.7 and 43.0°, respectively. The H atom of the methoxy group forms weak C—H···O intermolecular hydrogen bonds with the nitro group O atom of the neighbouring molecule. The H13B···O5i distance is 2.41 Å, which is considerable shorter than the sum of the van der Waals radii for O and H (2.70 Å). In the crystal structure, molecules are connected to form a one-dimension chain via weak C—H···O hydrogen bonds. In addition, there are also weak C—H···O hydrogen bonds between two one-dimension chains (Fig.2). The H14A···O6ii distance is 2.60 Å. These weak intermolecular C—H···O hydrogen bonds play an important role in stabilizing the crystal structure (symmetry operation: (i) 1 + x,y,z; (ii) 1 - x,1 - y,1 - z).

For related literature, see: Agrawal & Tratnyek (1996); Fischer et al. (2007); Chen et al. (2001); Ramkishen et al. (2005); Shinichi & Yuichiro (2005); Unver et al. (2002); Yang et al. (2005); Zhang (2006).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound shown using 30% probability ellipsoids.
[Figure 2] Fig. 2. Part of the title crystal structure with hydrogen bonds shown as dashed lines
6,6'-Dimethoxy-2,3,2',5'-tetranitro-1,1'-biphenyl top
Crystal data top
C14H10N4O10Z = 2
Mr = 394.26F(000) = 404
Triclinic, P1Dx = 1.589 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1821 (11) ÅCell parameters from 1810 reflections
b = 10.2161 (13) Åθ = 2.7–23.5°
c = 10.6133 (14) ŵ = 0.14 mm1
α = 95.118 (2)°T = 291 K
β = 90.579 (2)°Block, yellow
γ = 110.977 (2)°0.27 × 0.23 × 0.16 mm
V = 824.21 (19) Å3
Data collection top
Bruker APEX II CCD area-detector
diffractometer
3051 independent reflections
Radiation source: fine-focus sealed tube2173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.913, Tmax = 0.979k = 1212
6347 measured reflectionsl = 1212
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.06P)2 + 0.3203P]
where P = (Fo2 + 2Fc2)/3
3051 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.27 e Å3
48 restraintsΔρmin = 0.22 e Å3
Crystal data top
C14H10N4O10γ = 110.977 (2)°
Mr = 394.26V = 824.21 (19) Å3
Triclinic, P1Z = 2
a = 8.1821 (11) ÅMo Kα radiation
b = 10.2161 (13) ŵ = 0.14 mm1
c = 10.6133 (14) ÅT = 291 K
α = 95.118 (2)°0.27 × 0.23 × 0.16 mm
β = 90.579 (2)°
Data collection top
Bruker APEX II CCD area-detector
diffractometer
3051 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2173 reflections with I > 2σ(I)
Tmin = 0.913, Tmax = 0.979Rint = 0.017
6347 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04648 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å3
3051 reflectionsΔρmin = 0.22 e Å3
255 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.

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
O10.5521 (2)0.38404 (17)0.32635 (15)0.0544 (5)
O20.1047 (4)0.2166 (3)0.4665 (3)0.1216 (11)
O30.0829 (3)0.1796 (2)0.3485 (2)0.0847 (7)
O40.0530 (3)0.1066 (2)0.1089 (2)0.0836 (7)
O50.0687 (3)0.0425 (2)0.1627 (3)0.0909 (8)
O60.1341 (3)0.3722 (2)0.32138 (19)0.0735 (6)
O70.0125 (3)0.4502 (3)0.1823 (2)0.0864 (7)
O80.5697 (3)0.3399 (2)0.2476 (2)0.0972 (8)
O90.4681 (3)0.1229 (2)0.2111 (2)0.0861 (7)
O100.4716 (2)0.13198 (17)0.05720 (16)0.0505 (4)
N10.0619 (3)0.1446 (2)0.3991 (2)0.0620 (6)
N20.0430 (3)0.0071 (2)0.1743 (2)0.0520 (5)
N30.1122 (3)0.3936 (2)0.2140 (2)0.0504 (5)
N40.4869 (3)0.2450 (3)0.1846 (2)0.0614 (6)
C10.4371 (3)0.2571 (2)0.3497 (2)0.0416 (5)
C20.4469 (3)0.1889 (3)0.4556 (2)0.0502 (6)
H20.53650.23190.51710.060*
C30.3246 (3)0.0579 (3)0.4698 (2)0.0522 (6)
H30.33220.01270.54070.063*
C40.1917 (3)0.0063 (2)0.3801 (2)0.0446 (6)
C50.1809 (3)0.0619 (2)0.2745 (2)0.0384 (5)
C60.3011 (3)0.1926 (2)0.25653 (19)0.0364 (5)
C70.2998 (3)0.2600 (2)0.13651 (19)0.0357 (5)
C80.2142 (3)0.3520 (2)0.1146 (2)0.0406 (5)
C90.2197 (3)0.4097 (3)0.0016 (2)0.0488 (6)
H90.16010.47040.00980.059*
C100.3139 (3)0.3768 (3)0.0940 (2)0.0520 (7)
H100.32190.41730.16990.062*
C110.3963 (3)0.2837 (2)0.0768 (2)0.0443 (6)
C120.3931 (3)0.2246 (2)0.0373 (2)0.0395 (5)
C130.6577 (4)0.1862 (3)0.0691 (4)0.0756 (9)
H13A0.70460.21540.01060.113*
H13B0.69810.11440.09360.113*
H13C0.69610.26550.13230.113*
C140.6954 (4)0.4544 (3)0.4180 (3)0.0752 (9)
H14A0.64970.46770.49910.113*
H14B0.76520.54430.39160.113*
H14C0.76650.39790.42400.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0564 (11)0.0439 (9)0.0475 (10)0.0004 (8)0.0195 (8)0.0068 (8)
O20.113 (2)0.0900 (17)0.145 (2)0.0020 (15)0.0259 (18)0.0791 (18)
O30.0612 (14)0.0777 (15)0.0961 (17)0.0033 (11)0.0029 (12)0.0326 (12)
O40.0737 (14)0.0805 (15)0.0690 (13)0.0022 (12)0.0046 (11)0.0245 (12)
O50.0572 (13)0.0830 (15)0.129 (2)0.0206 (12)0.0363 (13)0.0153 (14)
O60.0964 (16)0.0887 (15)0.0536 (12)0.0538 (13)0.0126 (11)0.0124 (11)
O70.0846 (15)0.1112 (18)0.0920 (16)0.0701 (15)0.0017 (12)0.0103 (13)
O80.121 (2)0.0786 (15)0.0592 (13)0.0054 (14)0.0337 (13)0.0081 (11)
O90.1195 (19)0.0698 (15)0.0668 (14)0.0321 (14)0.0249 (13)0.0010 (11)
O100.0510 (10)0.0455 (9)0.0585 (11)0.0205 (8)0.0040 (8)0.0098 (8)
N10.0672 (16)0.0547 (14)0.0580 (14)0.0099 (12)0.0050 (12)0.0258 (11)
N20.0424 (12)0.0499 (13)0.0513 (13)0.0002 (10)0.0059 (10)0.0142 (11)
N30.0488 (12)0.0467 (12)0.0558 (14)0.0186 (10)0.0047 (10)0.0013 (10)
N40.0704 (15)0.0580 (15)0.0388 (12)0.0036 (12)0.0053 (11)0.0002 (11)
C10.0446 (13)0.0403 (12)0.0367 (12)0.0116 (11)0.0051 (10)0.0035 (10)
C20.0561 (15)0.0540 (15)0.0357 (13)0.0148 (12)0.0126 (11)0.0036 (11)
C30.0621 (16)0.0576 (16)0.0389 (13)0.0216 (13)0.0024 (12)0.0160 (11)
C40.0464 (13)0.0432 (13)0.0424 (13)0.0120 (11)0.0045 (10)0.0125 (10)
C50.0385 (12)0.0400 (12)0.0364 (12)0.0135 (10)0.0017 (9)0.0049 (9)
C60.0381 (12)0.0378 (12)0.0325 (11)0.0125 (10)0.0026 (9)0.0047 (9)
C70.0355 (11)0.0323 (11)0.0336 (11)0.0054 (9)0.0077 (9)0.0037 (9)
C80.0371 (12)0.0367 (12)0.0429 (13)0.0078 (10)0.0081 (10)0.0022 (10)
C90.0527 (14)0.0418 (13)0.0497 (14)0.0135 (11)0.0148 (12)0.0105 (11)
C100.0598 (16)0.0449 (14)0.0420 (14)0.0057 (12)0.0136 (12)0.0145 (11)
C110.0472 (13)0.0402 (12)0.0342 (12)0.0026 (11)0.0021 (10)0.0014 (10)
C120.0400 (12)0.0328 (11)0.0399 (12)0.0064 (10)0.0057 (10)0.0039 (9)
C130.0544 (17)0.0631 (18)0.110 (3)0.0250 (15)0.0126 (16)0.0002 (17)
C140.0695 (19)0.0616 (18)0.0679 (19)0.0081 (15)0.0308 (15)0.0075 (15)
Geometric parameters (Å, º) top
O1—C11.348 (3)C3—C41.370 (3)
O1—C141.444 (3)C3—H30.9300
O2—N11.203 (3)C4—C51.389 (3)
O3—N11.212 (3)C5—C61.377 (3)
O4—N21.206 (3)C6—C71.503 (3)
O5—N21.204 (3)C7—C81.391 (3)
O6—N31.203 (3)C7—C121.402 (3)
O7—N31.216 (3)C8—C91.377 (3)
O8—N41.225 (3)C9—C101.370 (4)
O9—N41.208 (3)C9—H90.9300
O10—C121.349 (3)C10—C111.371 (3)
O10—C131.422 (3)C10—H100.9300
N1—C41.465 (3)C11—C121.397 (3)
N2—C51.474 (3)C13—H13A0.9600
N3—C81.478 (3)C13—H13B0.9600
N4—C111.471 (3)C13—H13C0.9600
C1—C21.391 (3)C14—H14A0.9600
C1—C61.410 (3)C14—H14B0.9600
C2—C31.376 (4)C14—H14C0.9600
C2—H20.9300
C1—O1—C14117.70 (19)C1—C6—C7120.03 (19)
C12—O10—C13116.79 (19)C8—C7—C12117.51 (19)
O2—N1—O3123.6 (2)C8—C7—C6126.4 (2)
O2—N1—C4117.7 (2)C12—C7—C6116.11 (19)
O3—N1—C4118.7 (2)C9—C8—C7122.9 (2)
O5—N2—O4125.2 (2)C9—C8—N3116.4 (2)
O5—N2—C5117.1 (2)C7—C8—N3120.8 (2)
O4—N2—C5117.7 (2)C10—C9—C8119.3 (2)
O6—N3—O7123.7 (2)C10—C9—H9120.4
O6—N3—C8118.7 (2)C8—C9—H9120.4
O7—N3—C8117.6 (2)C9—C10—C11119.4 (2)
O9—N4—O8123.6 (2)C9—C10—H10120.3
O9—N4—C11119.4 (2)C11—C10—H10120.3
O8—N4—C11116.8 (2)C10—C11—C12122.2 (2)
O1—C1—C2124.6 (2)C10—C11—N4117.5 (2)
O1—C1—C6115.30 (19)C12—C11—N4120.4 (2)
C2—C1—C6120.1 (2)O10—C12—C11123.7 (2)
C3—C2—C1120.3 (2)O10—C12—C7117.54 (19)
C3—C2—H2119.9C11—C12—C7118.7 (2)
C1—C2—H2119.9O10—C13—H13A109.5
C4—C3—C2120.4 (2)O10—C13—H13B109.5
C4—C3—H3119.8H13A—C13—H13B109.5
C2—C3—H3119.8O10—C13—H13C109.5
C3—C4—C5119.5 (2)H13A—C13—H13C109.5
C3—C4—N1119.0 (2)H13B—C13—H13C109.5
C5—C4—N1121.5 (2)O1—C14—H14A109.5
C6—C5—C4121.9 (2)O1—C14—H14B109.5
C6—C5—N2117.51 (18)H14A—C14—H14B109.5
C4—C5—N2120.5 (2)O1—C14—H14C109.5
C5—C6—C1117.90 (19)H14A—C14—H14C109.5
C5—C6—C7121.83 (18)H14B—C14—H14C109.5
C14—O1—C1—C20.1 (4)C5—C6—C7—C1286.7 (3)
C14—O1—C1—C6179.3 (2)C1—C6—C7—C1287.5 (3)
O1—C1—C2—C3178.8 (2)C12—C7—C8—C90.9 (3)
C6—C1—C2—C30.3 (4)C6—C7—C8—C9179.9 (2)
C1—C2—C3—C40.3 (4)C12—C7—C8—N3179.59 (18)
C2—C3—C4—C50.1 (4)C6—C7—C8—N30.3 (3)
C2—C3—C4—N1178.9 (2)O6—N3—C8—C9163.8 (2)
O2—N1—C4—C324.1 (4)O7—N3—C8—C914.9 (3)
O3—N1—C4—C3154.7 (3)O6—N3—C8—C715.8 (3)
O2—N1—C4—C5157.1 (3)O7—N3—C8—C7165.5 (2)
O3—N1—C4—C524.1 (4)C7—C8—C9—C100.4 (3)
C3—C4—C5—C60.5 (4)N3—C8—C9—C10179.2 (2)
N1—C4—C5—C6179.3 (2)C8—C9—C10—C112.0 (3)
C3—C4—C5—N2177.7 (2)C9—C10—C11—C122.4 (3)
N1—C4—C5—N23.5 (4)C9—C10—C11—N4176.4 (2)
O5—N2—C5—C670.8 (3)O9—N4—C11—C10134.9 (3)
O4—N2—C5—C6107.7 (3)O8—N4—C11—C1040.7 (3)
O5—N2—C5—C4111.9 (3)O9—N4—C11—C1243.9 (3)
O4—N2—C5—C469.7 (3)O8—N4—C11—C12140.5 (3)
C4—C5—C6—C10.4 (3)C13—O10—C12—C1172.0 (3)
N2—C5—C6—C1177.7 (2)C13—O10—C12—C7109.6 (3)
C4—C5—C6—C7173.9 (2)C10—C11—C12—O10179.5 (2)
N2—C5—C6—C73.5 (3)N4—C11—C12—O100.7 (3)
O1—C1—C6—C5179.2 (2)C10—C11—C12—C71.2 (3)
C2—C1—C6—C50.0 (3)N4—C11—C12—C7177.63 (19)
O1—C1—C6—C74.8 (3)C8—C7—C12—O10177.95 (18)
C2—C1—C6—C7174.4 (2)C6—C7—C12—O101.4 (3)
C5—C6—C7—C892.6 (3)C8—C7—C12—C110.5 (3)
C1—C6—C7—C893.3 (3)C6—C7—C12—C11179.82 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O5i0.962.413.274 (4)150
C14—H14A···O6ii0.962.603.165 (3)118
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H10N4O10
Mr394.26
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)8.1821 (11), 10.2161 (13), 10.6133 (14)
α, β, γ (°)95.118 (2), 90.579 (2), 110.977 (2)
V3)824.21 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.27 × 0.23 × 0.16
Data collection
DiffractometerBruker APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.913, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
6347, 3051, 2173
Rint0.017
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.135, 1.04
No. of reflections3051
No. of parameters255
No. of restraints48
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13B···O5i0.962.413.274 (4)150.3
C14—H14A···O6ii0.962.603.165 (3)118.2
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1.
 

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