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In the title compound, C26H22N2O2, the two amide groups are twisted away from the attached naphthalene ring system by 63.94 (3) and 66.07 (3)°. The crystal packing is stabilized by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049495/ci2482sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049495/ci2482Isup2.hkl
Contains datablock I

CCDC reference: 667345

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.136
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C24 - C25 .. 8.64 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing, Qin, Gu, Zhang & Mao, 2006) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing, Qin, Gu, Zhang & Lei, 2006). We now report the crystal structure of the title compound, (I).

The bond lengths and angles in (I) are normal. The naphthalene ring system is planar, with a maximum deviation of 0.017 (1) Å for atom C2. As a result of steric effects, two amide groups (O1/N1/C1/C11 and O2/N2/C4/C19) are twisted away from the naphthalene mean plane by 63.94 (3) and 66.07 (3)°, respectively (Fig. 1). The dihedral angle between the O1/N1/C1/C11 and C13—C18 planes is 65.80 (5)°, and that between the O2/N2/C4/C19 and C21—C26 planes is 56.36 (6)°. The crystal packing is stabilized by intermolecular C—H···π interactions involving the C21—C26 phenyl ring (centroid Cg1; Table 1).

Related literature top

For applications of 1,4-naphthalenedicarboxylic acid derivatives, see: Fukuzumi et al. (1994) and Tsukada et al. (1994). For related structures, see: Jing, Qin, Gu, Zhang & Lei (2006); Jing, Qin, Gu, Zhang & Mao (2006).

Experimental top

Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was formed. N-Methyl phenylamine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 1 d. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethylsulfoxide and allowed to stand for one month at ambient temperature, after which time white single crystals of (I) suitable for X-ray diffraction were obtained.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.95 or 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C). The methyl groups were allowed to rotate but not to tip.

Structure description top

1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing, Qin, Gu, Zhang & Mao, 2006) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing, Qin, Gu, Zhang & Lei, 2006). We now report the crystal structure of the title compound, (I).

The bond lengths and angles in (I) are normal. The naphthalene ring system is planar, with a maximum deviation of 0.017 (1) Å for atom C2. As a result of steric effects, two amide groups (O1/N1/C1/C11 and O2/N2/C4/C19) are twisted away from the naphthalene mean plane by 63.94 (3) and 66.07 (3)°, respectively (Fig. 1). The dihedral angle between the O1/N1/C1/C11 and C13—C18 planes is 65.80 (5)°, and that between the O2/N2/C4/C19 and C21—C26 planes is 56.36 (6)°. The crystal packing is stabilized by intermolecular C—H···π interactions involving the C21—C26 phenyl ring (centroid Cg1; Table 1).

For applications of 1,4-naphthalenedicarboxylic acid derivatives, see: Fukuzumi et al. (1994) and Tsukada et al. (1994). For related structures, see: Jing, Qin, Gu, Zhang & Lei (2006); Jing, Qin, Gu, Zhang & Mao (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids.
N,N'-Dimethyl-N,N'-diphenylnaphthalene-1,4- dicarboxamide top
Crystal data top
C26H22N2O2Z = 2
Mr = 394.46F(000) = 416
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9970 (6) ÅCell parameters from 7714 reflections
b = 9.3627 (5) Åθ = 3.1–27.5°
c = 13.5538 (7) ŵ = 0.08 mm1
α = 105.329 (1)°T = 153 K
β = 92.391 (2)°Block, colourless
γ = 111.656 (2)°0.55 × 0.33 × 0.21 mm
V = 1010.95 (10) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3695 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.017
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1111
9974 measured reflectionsk = 1212
4593 independent reflectionsl = 1517
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.136 w = 1/[σ2(Fo2) + (0.0828P)2 + 0.279P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4593 reflectionsΔρmax = 0.35 e Å3
274 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (4)
Crystal data top
C26H22N2O2γ = 111.656 (2)°
Mr = 394.46V = 1010.95 (10) Å3
Triclinic, P1Z = 2
a = 8.9970 (6) ÅMo Kα radiation
b = 9.3627 (5) ŵ = 0.08 mm1
c = 13.5538 (7) ÅT = 153 K
α = 105.329 (1)°0.55 × 0.33 × 0.21 mm
β = 92.391 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3695 reflections with I > 2σ(I)
9974 measured reflectionsRint = 0.017
4593 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.00Δρmax = 0.35 e Å3
4593 reflectionsΔρmin = 0.26 e Å3
274 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
N10.78271 (13)0.56379 (13)0.00270 (8)0.0238 (2)
N20.77994 (13)0.57326 (13)0.52950 (8)0.0258 (3)
O10.80460 (13)0.32300 (11)0.03540 (7)0.0323 (2)
O20.81029 (13)0.33566 (11)0.47733 (7)0.0320 (2)
C10.78108 (15)0.44480 (14)0.13806 (9)0.0211 (3)
C20.90138 (15)0.56211 (14)0.21448 (10)0.0232 (3)
H20.98720.64290.19710.028*
C30.89866 (15)0.56371 (14)0.31845 (10)0.0234 (3)
H30.98340.64510.37060.028*
C40.77506 (15)0.44910 (14)0.34541 (9)0.0208 (3)
C50.51417 (15)0.20772 (15)0.29354 (10)0.0239 (3)
H50.50980.20920.36370.029*
C60.39271 (16)0.09150 (15)0.21772 (11)0.0281 (3)
H60.30480.01330.23560.034*
C70.39727 (16)0.08714 (16)0.11339 (11)0.0281 (3)
H70.31300.00540.06120.034*
C80.52240 (15)0.19998 (15)0.08664 (10)0.0239 (3)
H80.52360.19560.01590.029*
C90.65017 (14)0.32318 (14)0.16274 (9)0.0201 (3)
C100.64688 (14)0.32649 (13)0.26882 (9)0.0196 (3)
C110.79059 (15)0.43809 (15)0.02613 (10)0.0228 (3)
C120.79649 (18)0.56323 (18)0.11009 (10)0.0314 (3)
H12A0.91030.61860.11590.038*
H12B0.73310.61900.13080.038*
H12C0.75520.45180.15540.038*
C130.78233 (16)0.70820 (15)0.06758 (10)0.0233 (3)
C140.64906 (17)0.70588 (17)0.11556 (10)0.0292 (3)
H140.55750.60770.10380.035*
C150.6503 (2)0.84799 (19)0.18088 (12)0.0372 (4)
H150.55940.84690.21430.045*
C160.7831 (2)0.99164 (19)0.19777 (12)0.0420 (4)
H160.78321.08870.24260.050*
C170.9154 (2)0.99328 (18)0.14922 (13)0.0421 (4)
H171.00641.09180.16060.050*
C180.91587 (18)0.85181 (16)0.08391 (11)0.0324 (3)
H181.00700.85310.05060.039*
C190.78729 (15)0.44667 (15)0.45572 (9)0.0230 (3)
C200.81888 (19)0.5865 (2)0.63851 (10)0.0377 (4)
H20A0.78820.47840.64600.045*
H20B0.75910.64200.68060.045*
H20C0.93540.64780.66180.045*
C210.74327 (16)0.69856 (15)0.50824 (10)0.0265 (3)
C220.60438 (17)0.66366 (17)0.44191 (11)0.0298 (3)
H220.53370.55460.40880.036*
C230.5681 (2)0.7869 (2)0.42367 (14)0.0452 (4)
H230.47330.76160.37760.054*
C240.6678 (3)0.9448 (2)0.47155 (18)0.0592 (6)
H240.64281.02880.45840.071*
C250.8031 (3)0.98039 (19)0.53825 (18)0.0631 (7)
H250.87111.09000.57200.076*
C260.8442 (2)0.85844 (18)0.55828 (14)0.0451 (4)
H260.93870.88480.60490.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0268 (5)0.0250 (5)0.0212 (5)0.0105 (4)0.0082 (4)0.0084 (4)
N20.0271 (6)0.0300 (6)0.0192 (5)0.0122 (4)0.0031 (4)0.0043 (4)
O10.0445 (6)0.0268 (5)0.0272 (5)0.0163 (4)0.0127 (4)0.0067 (4)
O20.0407 (6)0.0317 (5)0.0287 (5)0.0183 (4)0.0022 (4)0.0120 (4)
C10.0233 (6)0.0218 (6)0.0223 (6)0.0123 (5)0.0060 (5)0.0080 (5)
C20.0218 (6)0.0202 (6)0.0272 (6)0.0072 (5)0.0056 (5)0.0080 (5)
C30.0223 (6)0.0195 (6)0.0259 (6)0.0079 (5)0.0019 (5)0.0039 (5)
C40.0237 (6)0.0199 (6)0.0214 (6)0.0119 (5)0.0041 (5)0.0055 (5)
C50.0258 (6)0.0238 (6)0.0238 (6)0.0108 (5)0.0081 (5)0.0077 (5)
C60.0239 (6)0.0236 (6)0.0331 (7)0.0059 (5)0.0086 (5)0.0072 (5)
C70.0230 (6)0.0245 (6)0.0297 (7)0.0062 (5)0.0010 (5)0.0017 (5)
C80.0255 (6)0.0247 (6)0.0209 (6)0.0112 (5)0.0024 (5)0.0040 (5)
C90.0208 (6)0.0195 (6)0.0219 (6)0.0107 (5)0.0044 (5)0.0053 (5)
C100.0211 (6)0.0184 (5)0.0213 (6)0.0107 (4)0.0043 (4)0.0047 (4)
C110.0210 (6)0.0240 (6)0.0220 (6)0.0073 (5)0.0049 (5)0.0066 (5)
C120.0402 (8)0.0383 (7)0.0225 (6)0.0190 (6)0.0121 (6)0.0139 (6)
C130.0280 (6)0.0251 (6)0.0216 (6)0.0136 (5)0.0045 (5)0.0103 (5)
C140.0290 (7)0.0358 (7)0.0278 (7)0.0162 (6)0.0065 (5)0.0123 (6)
C150.0438 (8)0.0498 (9)0.0317 (7)0.0327 (7)0.0111 (6)0.0128 (7)
C160.0638 (11)0.0347 (8)0.0360 (8)0.0318 (8)0.0044 (7)0.0065 (6)
C170.0513 (10)0.0259 (7)0.0440 (9)0.0114 (6)0.0032 (7)0.0086 (6)
C180.0334 (7)0.0295 (7)0.0339 (7)0.0103 (6)0.0088 (6)0.0116 (6)
C190.0212 (6)0.0252 (6)0.0215 (6)0.0085 (5)0.0017 (5)0.0065 (5)
C200.0412 (8)0.0539 (9)0.0185 (6)0.0246 (7)0.0008 (6)0.0037 (6)
C210.0293 (7)0.0229 (6)0.0264 (6)0.0097 (5)0.0135 (5)0.0054 (5)
C220.0354 (7)0.0320 (7)0.0303 (7)0.0181 (6)0.0141 (6)0.0139 (6)
C230.0608 (11)0.0530 (10)0.0519 (10)0.0407 (9)0.0329 (8)0.0335 (8)
C240.0801 (15)0.0446 (10)0.0856 (15)0.0423 (10)0.0564 (13)0.0394 (10)
C250.0787 (15)0.0202 (7)0.0832 (15)0.0115 (8)0.0504 (13)0.0100 (8)
C260.0413 (9)0.0280 (7)0.0492 (9)0.0028 (6)0.0187 (7)0.0013 (7)
Geometric parameters (Å, º) top
N1—C111.3583 (16)C12—H12B0.98
N1—C131.4347 (16)C12—H12C0.98
N1—C121.4647 (16)C13—C141.3836 (19)
N2—C191.3587 (16)C13—C181.3887 (18)
N2—C211.4229 (17)C14—C151.385 (2)
N2—C201.4660 (17)C14—H140.95
O1—C111.2273 (16)C15—C161.384 (2)
O2—C191.2343 (15)C15—H150.95
C1—C21.3704 (17)C16—C171.381 (3)
C1—C91.4283 (16)C16—H160.95
C1—C111.5091 (17)C17—C181.387 (2)
C2—C31.4067 (18)C17—H170.95
C2—H20.95C18—H180.95
C3—C41.3719 (17)C20—H20A0.98
C3—H30.95C20—H20B0.98
C4—C101.4207 (16)C20—H20C0.98
C4—C191.5014 (17)C21—C221.388 (2)
C5—C61.3681 (18)C21—C261.3906 (19)
C5—C101.4230 (17)C22—C231.386 (2)
C5—H50.95C22—H220.95
C6—C71.4066 (19)C23—C241.370 (3)
C6—H60.95C23—H230.95
C7—C81.3688 (18)C24—C251.364 (3)
C7—H70.95C24—H240.95
C8—C91.4174 (17)C25—C261.408 (3)
C8—H80.95C25—H250.95
C9—C101.4317 (17)C26—H260.95
C12—H12A0.98
C11—N1—C13124.44 (10)C14—C13—C18120.41 (12)
C11—N1—C12118.52 (11)C14—C13—N1120.69 (11)
C13—N1—C12116.55 (10)C18—C13—N1118.86 (12)
C19—N2—C21124.32 (11)C13—C14—C15119.45 (13)
C19—N2—C20118.31 (11)C13—C14—H14120.3
C21—N2—C20117.32 (11)C15—C14—H14120.3
C2—C1—C9120.60 (11)C16—C15—C14120.51 (14)
C2—C1—C11120.02 (11)C16—C15—H15119.7
C9—C1—C11119.30 (11)C14—C15—H15119.7
C1—C2—C3120.47 (11)C17—C16—C15119.75 (14)
C1—C2—H2119.8C17—C16—H16120.1
C3—C2—H2119.8C15—C16—H16120.1
C4—C3—C2120.75 (11)C16—C17—C18120.32 (15)
C4—C3—H3119.6C16—C17—H17119.8
C2—C3—H3119.6C18—C17—H17119.8
C3—C4—C10120.63 (11)C17—C18—C13119.55 (14)
C3—C4—C19118.30 (11)C17—C18—H18120.2
C10—C4—C19120.79 (11)C13—C18—H18120.2
C6—C5—C10120.94 (12)O2—C19—N2122.19 (12)
C6—C5—H5119.5O2—C19—C4120.00 (11)
C10—C5—H5119.5N2—C19—C4117.74 (11)
C5—C6—C7120.34 (12)N2—C20—H20A109.5
C5—C6—H6119.8N2—C20—H20B109.5
C7—C6—H6119.8H20A—C20—H20B109.5
C8—C7—C6120.41 (12)N2—C20—H20C109.5
C8—C7—H7119.8H20A—C20—H20C109.5
C6—C7—H7119.8H20B—C20—H20C109.5
C7—C8—C9121.13 (12)C22—C21—C26119.48 (14)
C7—C8—H8119.4C22—C21—N2120.95 (11)
C9—C8—H8119.4C26—C21—N2119.50 (14)
C8—C9—C1122.74 (11)C23—C22—C21120.40 (15)
C8—C9—C10118.54 (11)C23—C22—H22119.8
C1—C9—C10118.72 (11)C21—C22—H22119.8
C4—C10—C5122.54 (11)C24—C23—C22120.59 (18)
C4—C10—C9118.83 (11)C24—C23—H23119.7
C5—C10—C9118.63 (11)C22—C23—H23119.7
O1—C11—N1122.12 (11)C25—C24—C23119.46 (17)
O1—C11—C1120.70 (11)C25—C24—H24120.3
N1—C11—C1117.18 (10)C23—C24—H24120.3
N1—C12—H12A109.5C24—C25—C26121.53 (16)
N1—C12—H12B109.5C24—C25—H25119.2
H12A—C12—H12B109.5C26—C25—H25119.2
N1—C12—H12C109.5C21—C26—C25118.52 (19)
H12A—C12—H12C109.5C21—C26—H26120.7
H12B—C12—H12C109.5C25—C26—H26120.7
C9—C1—C2—C30.62 (18)C11—N1—C13—C1470.76 (17)
C11—C1—C2—C3176.18 (11)C12—N1—C13—C14117.40 (13)
C1—C2—C3—C40.63 (19)C11—N1—C13—C18111.51 (14)
C2—C3—C4—C100.15 (18)C12—N1—C13—C1860.33 (16)
C2—C3—C4—C19173.82 (11)C18—C13—C14—C150.5 (2)
C10—C5—C6—C70.19 (19)N1—C13—C14—C15178.25 (12)
C5—C6—C7—C80.6 (2)C13—C14—C15—C160.4 (2)
C6—C7—C8—C90.2 (2)C14—C15—C16—C170.1 (2)
C7—C8—C9—C1178.76 (12)C15—C16—C17—C180.1 (2)
C7—C8—C9—C100.67 (18)C16—C17—C18—C130.0 (2)
C2—C1—C9—C8179.58 (11)C14—C13—C18—C170.3 (2)
C11—C1—C9—C83.59 (18)N1—C13—C18—C17178.08 (13)
C2—C1—C9—C100.16 (17)C21—N2—C19—O2175.71 (12)
C11—C1—C9—C10176.98 (10)C20—N2—C19—O27.03 (19)
C3—C4—C10—C5178.34 (11)C21—N2—C19—C47.42 (18)
C19—C4—C10—C57.84 (17)C20—N2—C19—C4169.84 (12)
C3—C4—C10—C90.91 (17)C3—C4—C19—O2109.93 (14)
C19—C4—C10—C9172.90 (10)C10—C4—C19—O264.03 (16)
C6—C5—C10—C4179.92 (12)C3—C4—C19—N267.01 (15)
C6—C5—C10—C90.66 (18)C10—C4—C19—N2119.03 (13)
C8—C9—C10—C4179.64 (10)C19—N2—C21—C2253.51 (18)
C1—C9—C10—C40.91 (16)C20—N2—C21—C22129.20 (14)
C8—C9—C10—C51.07 (17)C19—N2—C21—C26129.46 (14)
C1—C9—C10—C5178.38 (10)C20—N2—C21—C2647.84 (17)
C13—N1—C11—O1173.60 (12)C26—C21—C22—C231.5 (2)
C12—N1—C11—O11.91 (18)N2—C21—C22—C23178.52 (12)
C13—N1—C11—C16.50 (17)C21—C22—C23—C240.7 (2)
C12—N1—C11—C1178.19 (11)C22—C23—C24—C250.5 (3)
C2—C1—C11—O1115.16 (14)C23—C24—C25—C260.8 (3)
C9—C1—C11—O161.68 (16)C22—C21—C26—C251.2 (2)
C2—C1—C11—N164.93 (16)N2—C21—C26—C25178.23 (13)
C9—C1—C11—N1118.22 (12)C24—C25—C26—C210.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.952.823.614 (1)142
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H22N2O2
Mr394.46
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)8.9970 (6), 9.3627 (5), 13.5538 (7)
α, β, γ (°)105.329 (1), 92.391 (2), 111.656 (2)
V3)1010.95 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.55 × 0.33 × 0.21
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9974, 4593, 3695
Rint0.017
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.136, 1.00
No. of reflections4593
No. of parameters274
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.26

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.952.823.614 (1)142
Symmetry code: (i) x+1, y+1, z+1.
 

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