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The title compound, C36H26N2O2, crystallizes with two mol­ecules in the asymmetric unit. The two mol­ecules differ slightly in the orientations of the phenyl rings; the dihedral angles between the two phenyl rings attached to each N atom are 68.77 (1)/83.28 (1) and 74.05 (1)/64.84 (1)°. The crystal packing is stabilized by C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051495/ci2483sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051495/ci2483Isup2.hkl
Contains datablock I

CCDC reference: 667427

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.066
  • wR factor = 0.192
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.692 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.69 e/A    PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact C2 .. C2 .. 3.17 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 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

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 asymmetric unit of (I) consists of two crystallographically independent molecules which differ in the orientations of the phenyl groups (Fig. 1). Bond lengths and angles of these two molecules agree with each other and are normal. In both independent molecules, the naphthalene ring systems are planar, with maximum deviation of 0.039 (4) Å for atom C6 and 0.032 (3) Å for atom C45. As a result of steric effects, the substituent groups are twisted away from the planes of the naphthalene ring systems (Fig. 1). The dihedral angles formed between various planes are as follows: C1—C10 and O1/N1/C1/C11 66.7 (2)°, C1—C10 and O2/N2/C4/C24 61.1 (2)°, C37—C46 and O3/N3/C37/C47 59.4 (2)°, C37—C46 and O4/N4/C40/C60 89.5 (2)°, O1/N1/C1/C11 and C12—C17 69.4 (2)°, O1/N1/C1/C11 and C18—C23 65.4 (2)°, O2/N2/C4/C24 and C25—C30 68.3 (2)°, O2/N2/C4/C24 and C31—C36 52.8 (2)°, O3/N3/C37/C47 and C48—C53 63.3 (2)°, O3/N3/C37/C47 and C54—C59 54.8 (2)°, O4/N4/C40/C60 and C61—C66 58.0 (2)°, O4/N4/C40/C60 and C67—C72 82.1 (2)°, C12—C17 and C18—C23 68.8 (2)°, C25—C30 and C31—C36 83.3 (2)°, C48—C53 and C54—C59 74.0 (2)° and C61—C66 and C67—C72 64.8 (2)°. The crystal packing is stabilized by C—H···O hydrogen bonds and C—H···π interactions (Table 1; Cg1, Cg2, Cg3 and Cg4 are the centroids of the C12—C17, C25—C30, C31—C36 and C61—C66 rings, respectively)

Related literature top

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

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. Diphenylamine (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 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

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 asymmetric unit of (I) consists of two crystallographically independent molecules which differ in the orientations of the phenyl groups (Fig. 1). Bond lengths and angles of these two molecules agree with each other and are normal. In both independent molecules, the naphthalene ring systems are planar, with maximum deviation of 0.039 (4) Å for atom C6 and 0.032 (3) Å for atom C45. As a result of steric effects, the substituent groups are twisted away from the planes of the naphthalene ring systems (Fig. 1). The dihedral angles formed between various planes are as follows: C1—C10 and O1/N1/C1/C11 66.7 (2)°, C1—C10 and O2/N2/C4/C24 61.1 (2)°, C37—C46 and O3/N3/C37/C47 59.4 (2)°, C37—C46 and O4/N4/C40/C60 89.5 (2)°, O1/N1/C1/C11 and C12—C17 69.4 (2)°, O1/N1/C1/C11 and C18—C23 65.4 (2)°, O2/N2/C4/C24 and C25—C30 68.3 (2)°, O2/N2/C4/C24 and C31—C36 52.8 (2)°, O3/N3/C37/C47 and C48—C53 63.3 (2)°, O3/N3/C37/C47 and C54—C59 54.8 (2)°, O4/N4/C40/C60 and C61—C66 58.0 (2)°, O4/N4/C40/C60 and C67—C72 82.1 (2)°, C12—C17 and C18—C23 68.8 (2)°, C25—C30 and C31—C36 83.3 (2)°, C48—C53 and C54—C59 74.0 (2)° and C61—C66 and C67—C72 64.8 (2)°. The crystal packing is stabilized by C—H···O hydrogen bonds and C—H···π interactions (Table 1; Cg1, Cg2, Cg3 and Cg4 are the centroids of the C12—C17, C25—C30, C31—C36 and C61—C66 rings, respectively)

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

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,N',N'-Tetraphenylnaphthalene-1,4-dicarboxamide top
Crystal data top
C36H26N2O2Z = 4
Mr = 518.59F(000) = 1088
Triclinic, P1Dx = 1.312 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0276 (8) ÅCell parameters from 13361 reflections
b = 13.4211 (11) Åθ = 3.0–27.5°
c = 20.2414 (13) ŵ = 0.08 mm1
α = 88.560 (2)°T = 153 K
β = 89.279 (2)°Block, white
γ = 74.523 (3)°0.49 × 0.28 × 0.21 mm
V = 2624.5 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5904 reflections with I > 2σ(I)
Radiation source: Rotating anodeRint = 0.055
Graphite monochromatorθmax = 25.5°, θmin = 3.0°
ω scansh = 1212
20350 measured reflectionsk = 1616
9674 independent reflectionsl = 2423
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.192 w = 1/[σ2(Fo2) + (0.061P)2 + 5P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
9674 reflectionsΔρmax = 0.69 e Å3
722 parametersΔρmin = 0.40 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: 0.0062 (8)
Crystal data top
C36H26N2O2γ = 74.523 (3)°
Mr = 518.59V = 2624.5 (3) Å3
Triclinic, P1Z = 4
a = 10.0276 (8) ÅMo Kα radiation
b = 13.4211 (11) ŵ = 0.08 mm1
c = 20.2414 (13) ÅT = 153 K
α = 88.560 (2)°0.49 × 0.28 × 0.21 mm
β = 89.279 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5904 reflections with I > 2σ(I)
20350 measured reflectionsRint = 0.055
9674 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.192H-atom parameters constrained
S = 1.00Δρmax = 0.69 e Å3
9674 reflectionsΔρmin = 0.40 e Å3
722 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
O10.5048 (2)0.74330 (18)0.48167 (10)0.0295 (5)
O20.1292 (3)1.2351 (2)0.56123 (12)0.0428 (7)
O31.0879 (3)0.0431 (2)0.93001 (12)0.0415 (7)
O40.6618 (3)0.5119 (2)1.01899 (11)0.0357 (6)
N10.6095 (3)0.7125 (2)0.58195 (12)0.0269 (6)
N20.2346 (3)1.2341 (2)0.65984 (13)0.0303 (7)
N30.9590 (3)0.0321 (2)0.84020 (13)0.0325 (7)
N40.6043 (3)0.5654 (2)0.91324 (12)0.0273 (6)
C10.4381 (3)0.8770 (3)0.55987 (14)0.0264 (7)
C20.5034 (3)0.9527 (2)0.57279 (14)0.0241 (7)
H20.60150.93680.57030.029*
C30.4280 (3)1.0518 (3)0.58946 (14)0.0281 (8)
H30.47511.10290.59790.034*
C40.2851 (3)1.0769 (3)0.59392 (15)0.0283 (8)
C50.0682 (4)1.0197 (3)0.59077 (17)0.0382 (9)
H50.01531.08660.60310.046*
C60.0036 (4)0.9439 (3)0.58117 (18)0.0402 (9)
H60.09360.95810.58770.048*
C70.0786 (4)0.8459 (3)0.56193 (18)0.0411 (9)
H70.03170.79450.55410.049*
C80.2189 (4)0.8230 (3)0.55423 (16)0.0334 (8)
H80.26900.75550.54170.040*
C90.2905 (3)0.8995 (3)0.56481 (14)0.0258 (7)
C100.2151 (3)0.9997 (3)0.58244 (15)0.0276 (7)
C110.5192 (3)0.7723 (3)0.53754 (15)0.0251 (7)
C120.6774 (3)0.6061 (3)0.56730 (14)0.0247 (7)
C130.5991 (3)0.5355 (3)0.56387 (15)0.0276 (7)
H130.50110.55870.56670.033*
C140.6627 (4)0.4318 (3)0.55629 (15)0.0318 (8)
H140.60840.38400.55290.038*
C150.8050 (4)0.3975 (3)0.55365 (15)0.0310 (8)
H150.84930.32580.55010.037*
C160.8833 (4)0.4686 (3)0.55627 (16)0.0316 (8)
H160.98130.44530.55410.038*
C170.8197 (3)0.5728 (3)0.56202 (15)0.0302 (8)
H170.87360.62120.56240.036*
C180.6154 (4)0.7416 (3)0.64971 (15)0.0287 (8)
C190.7372 (4)0.7577 (3)0.67385 (18)0.0357 (9)
H190.81570.75150.64590.043*
C200.7414 (4)0.7832 (3)0.73996 (19)0.0457 (11)
H200.82480.79170.75770.055*
C210.6258 (5)0.7962 (3)0.77997 (18)0.0459 (11)
H210.62880.81620.82450.055*
C220.5064 (4)0.7801 (3)0.75530 (17)0.0407 (9)
H220.42710.78830.78290.049*
C230.5018 (4)0.7522 (3)0.69054 (16)0.0357 (9)
H230.41940.74020.67390.043*
C240.2087 (4)1.1875 (3)0.60324 (16)0.0311 (8)
C250.1900 (3)1.3461 (3)0.66238 (15)0.0271 (7)
C260.0965 (3)1.3928 (3)0.71010 (16)0.0313 (8)
H260.06041.35190.74080.038*
C270.0553 (4)1.5001 (3)0.71307 (17)0.0360 (9)
H270.00871.53280.74600.043*
C280.1079 (4)1.5592 (3)0.66786 (17)0.0359 (9)
H280.07901.63260.66920.043*
C290.2031 (4)1.5105 (3)0.62054 (16)0.0331 (8)
H290.24011.55100.58990.040*
C300.2449 (4)1.4037 (3)0.61751 (16)0.0318 (8)
H300.31001.37060.58510.038*
C310.3036 (4)1.1801 (3)0.71727 (15)0.0296 (8)
C320.3998 (4)1.2187 (3)0.74882 (17)0.0341 (8)
H320.42261.27840.73140.041*
C330.4629 (4)1.1706 (3)0.80566 (18)0.0413 (10)
H330.52701.19860.82790.050*
C340.4336 (4)1.0820 (3)0.83032 (17)0.0442 (10)
H340.47891.04820.86880.053*
C350.3383 (4)1.0429 (3)0.79884 (17)0.0401 (9)
H350.31830.98170.81560.048*
C360.2712 (4)1.0926 (3)0.74273 (16)0.0350 (8)
H360.20331.06670.72190.042*
C370.9085 (4)0.1931 (3)0.90240 (15)0.0282 (8)
C380.7680 (4)0.2105 (3)0.91349 (16)0.0319 (8)
H380.72590.15540.90960.038*
C390.6872 (4)0.3090 (3)0.93039 (15)0.0286 (7)
H390.59080.31960.93810.034*
C400.7443 (4)0.3892 (3)0.93589 (15)0.0284 (8)
C410.9507 (4)0.4578 (3)0.92473 (16)0.0333 (8)
H410.89610.52450.93630.040*
C421.0879 (4)0.4434 (3)0.91044 (17)0.0382 (9)
H421.12770.50010.91190.046*
C431.1698 (4)0.3458 (3)0.89371 (17)0.0368 (9)
H431.26510.33660.88360.044*
C441.1141 (4)0.2630 (3)0.89171 (17)0.0358 (9)
H441.17110.19680.88060.043*
C450.9712 (3)0.2758 (3)0.90621 (15)0.0293 (8)
C460.8887 (3)0.3748 (3)0.92251 (15)0.0263 (7)
C470.9939 (4)0.0847 (3)0.89241 (16)0.0318 (8)
C481.0115 (4)0.0788 (3)0.83908 (17)0.0320 (8)
C490.9870 (4)0.1382 (3)0.89221 (19)0.0435 (10)
H490.93870.10630.93010.052*
C501.0338 (5)0.2450 (3)0.8895 (2)0.0502 (11)
H501.01740.28650.92580.060*
C511.1044 (4)0.2920 (3)0.8341 (2)0.0471 (11)
H511.13550.36520.83240.057*
C521.1289 (4)0.2318 (3)0.7823 (2)0.0428 (10)
H521.17800.26360.74450.051*
C531.0827 (4)0.1246 (3)0.78424 (18)0.0366 (9)
H531.10000.08320.74800.044*
C540.8826 (4)0.0821 (3)0.78338 (16)0.0306 (8)
C550.7856 (4)0.0398 (3)0.75558 (18)0.0390 (9)
H550.76540.01930.77560.047*
C560.7179 (4)0.0837 (3)0.69838 (19)0.0449 (10)
H560.65360.05290.67860.054*
C570.7423 (4)0.1711 (3)0.66984 (18)0.0440 (10)
H570.69430.20130.63100.053*
C580.8375 (4)0.2149 (3)0.69816 (17)0.0422 (10)
H580.85390.27600.67910.051*
C590.9090 (4)0.1698 (3)0.75415 (16)0.0354 (8)
H590.97630.19900.77260.042*
C600.6635 (3)0.4933 (3)0.95938 (15)0.0264 (7)
C610.5503 (4)0.6726 (3)0.93096 (15)0.0303 (8)
C620.6368 (4)0.7212 (3)0.96301 (18)0.0401 (9)
H620.72980.68450.97240.048*
C630.5869 (4)0.8231 (3)0.98110 (19)0.0466 (10)
H630.64420.85591.00450.056*
C640.4523 (5)0.8772 (3)0.96485 (19)0.0473 (10)
H640.41960.94810.97570.057*
C650.3659 (4)0.8300 (3)0.93334 (17)0.0396 (9)
H650.27350.86710.92330.048*
C660.4166 (4)0.7262 (3)0.91635 (16)0.0367 (9)
H660.35800.69260.89450.044*
C670.5813 (3)0.5334 (3)0.84756 (15)0.0287 (8)
C680.4591 (4)0.5074 (3)0.83508 (16)0.0312 (8)
H680.39190.51080.86910.037*
C690.4365 (4)0.4764 (3)0.77233 (16)0.0366 (9)
H690.35220.46030.76270.044*
C700.5365 (4)0.4691 (3)0.72372 (16)0.0344 (8)
H700.52150.44650.68100.041*
C710.6583 (4)0.4945 (3)0.73674 (16)0.0339 (8)
H710.72710.48900.70330.041*
C720.6790 (3)0.5279 (3)0.79878 (15)0.0305 (8)
H720.76130.54730.80770.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0352 (13)0.0278 (14)0.0258 (11)0.0084 (11)0.0037 (10)0.0024 (9)
O20.0499 (16)0.0291 (15)0.0441 (14)0.0003 (12)0.0239 (12)0.0042 (11)
O30.0469 (16)0.0324 (15)0.0421 (14)0.0042 (12)0.0173 (12)0.0016 (11)
O40.0434 (15)0.0360 (15)0.0267 (12)0.0084 (12)0.0033 (10)0.0026 (10)
N10.0333 (15)0.0216 (15)0.0247 (13)0.0053 (12)0.0043 (11)0.0032 (11)
N20.0355 (16)0.0246 (16)0.0263 (14)0.0006 (13)0.0073 (12)0.0042 (11)
N30.0390 (17)0.0250 (16)0.0315 (15)0.0045 (13)0.0083 (12)0.0021 (12)
N40.0310 (15)0.0230 (15)0.0252 (13)0.0021 (12)0.0020 (11)0.0026 (11)
C10.0306 (17)0.0285 (19)0.0188 (14)0.0054 (15)0.0056 (13)0.0014 (13)
C20.0245 (16)0.0235 (18)0.0255 (15)0.0083 (14)0.0033 (12)0.0004 (13)
C30.0350 (19)0.0269 (19)0.0218 (15)0.0066 (15)0.0063 (13)0.0017 (13)
C40.0318 (18)0.0265 (19)0.0241 (15)0.0030 (15)0.0042 (13)0.0049 (13)
C50.034 (2)0.039 (2)0.0400 (19)0.0044 (17)0.0075 (16)0.0097 (16)
C60.0259 (18)0.049 (3)0.048 (2)0.0133 (18)0.0043 (16)0.0138 (18)
C70.037 (2)0.043 (2)0.046 (2)0.0137 (18)0.0043 (17)0.0109 (18)
C80.036 (2)0.030 (2)0.0363 (18)0.0128 (16)0.0035 (15)0.0061 (15)
C90.0298 (17)0.0253 (18)0.0228 (15)0.0077 (14)0.0010 (13)0.0035 (13)
C100.0332 (18)0.0242 (18)0.0263 (16)0.0086 (15)0.0064 (13)0.0034 (13)
C110.0266 (17)0.0245 (18)0.0265 (16)0.0108 (14)0.0024 (13)0.0002 (13)
C120.0261 (17)0.0267 (18)0.0212 (14)0.0066 (14)0.0021 (12)0.0012 (13)
C130.0286 (17)0.0280 (19)0.0289 (16)0.0120 (15)0.0036 (13)0.0004 (13)
C140.040 (2)0.029 (2)0.0279 (16)0.0100 (16)0.0066 (15)0.0020 (14)
C150.043 (2)0.0256 (19)0.0234 (16)0.0065 (16)0.0067 (14)0.0008 (13)
C160.0263 (17)0.035 (2)0.0328 (17)0.0057 (15)0.0033 (14)0.0063 (15)
C170.0285 (18)0.032 (2)0.0308 (17)0.0091 (15)0.0029 (14)0.0033 (14)
C180.0342 (19)0.0230 (18)0.0269 (16)0.0039 (15)0.0034 (14)0.0021 (13)
C190.0339 (19)0.033 (2)0.0414 (19)0.0101 (17)0.0071 (16)0.0037 (16)
C200.052 (3)0.037 (2)0.048 (2)0.0094 (19)0.023 (2)0.0064 (18)
C210.075 (3)0.033 (2)0.0285 (18)0.011 (2)0.0094 (19)0.0004 (15)
C220.056 (2)0.036 (2)0.0288 (18)0.0096 (19)0.0009 (17)0.0021 (15)
C230.043 (2)0.034 (2)0.0298 (17)0.0101 (17)0.0028 (15)0.0023 (15)
C240.0311 (18)0.028 (2)0.0314 (17)0.0037 (15)0.0038 (14)0.0038 (14)
C250.0287 (17)0.0221 (18)0.0261 (16)0.0012 (14)0.0042 (13)0.0062 (13)
C260.0310 (18)0.032 (2)0.0320 (17)0.0108 (16)0.0018 (14)0.0030 (14)
C270.035 (2)0.032 (2)0.0389 (19)0.0050 (17)0.0033 (15)0.0088 (16)
C280.039 (2)0.029 (2)0.0383 (19)0.0045 (16)0.0128 (16)0.0024 (15)
C290.038 (2)0.034 (2)0.0297 (17)0.0129 (16)0.0082 (15)0.0013 (14)
C300.0341 (19)0.034 (2)0.0250 (16)0.0043 (16)0.0048 (14)0.0046 (14)
C310.0354 (19)0.0242 (19)0.0258 (16)0.0018 (15)0.0034 (14)0.0036 (13)
C320.0349 (19)0.032 (2)0.0360 (18)0.0098 (16)0.0055 (15)0.0032 (15)
C330.039 (2)0.043 (2)0.040 (2)0.0054 (18)0.0110 (17)0.0056 (17)
C340.045 (2)0.050 (3)0.0291 (18)0.001 (2)0.0053 (16)0.0009 (17)
C350.051 (2)0.032 (2)0.0330 (18)0.0039 (18)0.0045 (17)0.0033 (15)
C360.042 (2)0.032 (2)0.0305 (17)0.0085 (17)0.0020 (15)0.0042 (15)
C370.0358 (19)0.0222 (18)0.0270 (16)0.0080 (15)0.0070 (14)0.0008 (13)
C380.0339 (19)0.031 (2)0.0316 (17)0.0104 (16)0.0059 (14)0.0012 (14)
C390.0284 (17)0.0279 (19)0.0290 (16)0.0064 (15)0.0015 (13)0.0026 (14)
C400.0363 (19)0.0254 (19)0.0231 (15)0.0071 (15)0.0046 (13)0.0002 (13)
C410.036 (2)0.030 (2)0.0344 (18)0.0100 (16)0.0013 (15)0.0049 (15)
C420.040 (2)0.038 (2)0.0386 (19)0.0127 (18)0.0020 (16)0.0054 (16)
C430.0300 (19)0.040 (2)0.0419 (19)0.0118 (17)0.0018 (15)0.0087 (16)
C440.0335 (19)0.038 (2)0.0343 (18)0.0063 (17)0.0005 (15)0.0094 (15)
C450.0319 (18)0.032 (2)0.0236 (15)0.0080 (15)0.0061 (13)0.0008 (13)
C460.0300 (17)0.0250 (18)0.0246 (15)0.0084 (14)0.0002 (13)0.0035 (13)
C470.0348 (19)0.031 (2)0.0303 (17)0.0088 (16)0.0030 (15)0.0001 (14)
C480.0331 (19)0.0235 (19)0.0377 (18)0.0039 (15)0.0095 (15)0.0041 (14)
C490.049 (2)0.033 (2)0.047 (2)0.0103 (19)0.0019 (18)0.0002 (17)
C500.060 (3)0.028 (2)0.062 (3)0.012 (2)0.007 (2)0.0086 (19)
C510.044 (2)0.030 (2)0.066 (3)0.0063 (18)0.018 (2)0.0011 (19)
C520.037 (2)0.033 (2)0.057 (2)0.0049 (18)0.0097 (18)0.0138 (18)
C530.040 (2)0.031 (2)0.0402 (19)0.0112 (17)0.0022 (16)0.0057 (16)
C540.0345 (19)0.0255 (19)0.0291 (16)0.0032 (15)0.0034 (14)0.0027 (14)
C550.0325 (19)0.040 (2)0.047 (2)0.0126 (17)0.0077 (16)0.0055 (17)
C560.038 (2)0.050 (3)0.043 (2)0.0035 (19)0.0108 (17)0.0074 (19)
C570.043 (2)0.046 (3)0.0327 (19)0.0059 (19)0.0048 (16)0.0017 (17)
C580.051 (2)0.038 (2)0.0342 (19)0.0066 (19)0.0038 (17)0.0020 (16)
C590.045 (2)0.029 (2)0.0321 (18)0.0085 (17)0.0023 (15)0.0024 (15)
C600.0279 (17)0.0234 (18)0.0289 (16)0.0085 (14)0.0027 (13)0.0014 (13)
C610.0332 (18)0.033 (2)0.0229 (15)0.0055 (16)0.0010 (13)0.0026 (14)
C620.040 (2)0.032 (2)0.046 (2)0.0035 (17)0.0046 (17)0.0073 (16)
C630.053 (3)0.040 (2)0.047 (2)0.011 (2)0.0046 (19)0.0082 (18)
C640.066 (3)0.031 (2)0.044 (2)0.012 (2)0.002 (2)0.0001 (17)
C650.046 (2)0.033 (2)0.0309 (18)0.0055 (18)0.0064 (16)0.0007 (15)
C660.042 (2)0.033 (2)0.0320 (18)0.0041 (17)0.0082 (16)0.0052 (15)
C670.0323 (18)0.0285 (19)0.0219 (15)0.0019 (15)0.0055 (13)0.0012 (13)
C680.0327 (18)0.032 (2)0.0294 (17)0.0097 (16)0.0000 (14)0.0015 (14)
C690.039 (2)0.040 (2)0.0314 (17)0.0109 (18)0.0065 (15)0.0031 (16)
C700.045 (2)0.037 (2)0.0238 (16)0.0161 (17)0.0034 (15)0.0032 (14)
C710.039 (2)0.034 (2)0.0275 (17)0.0089 (17)0.0013 (15)0.0001 (14)
C720.0271 (17)0.036 (2)0.0286 (16)0.0086 (16)0.0008 (13)0.0012 (14)
Geometric parameters (Å, º) top
O1—C111.228 (4)C32—H320.95
O2—C241.219 (4)C33—C341.379 (6)
O3—C471.223 (4)C33—H330.95
O4—C601.237 (4)C34—C351.376 (6)
N1—C111.366 (4)C34—H340.95
N1—C181.442 (4)C35—C361.389 (5)
N1—C121.446 (4)C35—H350.95
N2—C241.379 (4)C36—H360.95
N2—C311.437 (4)C37—C381.382 (5)
N2—C251.452 (4)C37—C451.418 (5)
N3—C471.384 (4)C37—C471.495 (5)
N3—C541.438 (4)C38—C391.401 (5)
N3—C481.441 (4)C38—H380.95
N4—C601.350 (4)C39—C401.356 (5)
N4—C671.447 (4)C39—H390.95
N4—C611.449 (4)C40—C461.432 (5)
C1—C21.379 (5)C40—C601.501 (5)
C1—C91.433 (5)C41—C421.365 (5)
C1—C111.501 (4)C41—C461.415 (5)
C2—C31.391 (4)C41—H410.95
C2—H20.95C42—C431.395 (5)
C3—C41.384 (5)C42—H420.95
C3—H30.95C43—C441.373 (5)
C4—C101.423 (5)C43—H430.95
C4—C241.493 (5)C44—C451.425 (5)
C5—C61.363 (5)C44—H440.95
C5—C101.433 (5)C45—C461.410 (5)
C5—H50.95C48—C531.378 (5)
C6—C71.392 (5)C48—C491.381 (5)
C6—H60.95C49—C501.387 (6)
C7—C81.365 (5)C49—H490.95
C7—H70.95C50—C511.389 (6)
C8—C91.422 (5)C50—H500.95
C8—H80.95C51—C521.368 (6)
C9—C101.408 (4)C51—H510.95
C12—C171.381 (5)C52—C531.390 (5)
C12—C131.385 (5)C52—H520.95
C13—C141.378 (5)C53—H530.95
C13—H130.95C54—C551.382 (5)
C14—C151.379 (5)C54—C591.391 (5)
C14—H140.95C55—C561.386 (5)
C15—C161.390 (5)C55—H550.95
C15—H150.95C56—C571.373 (6)
C16—C171.380 (5)C56—H560.95
C16—H160.95C57—C581.384 (6)
C17—H170.95C57—H570.95
C18—C231.378 (5)C58—C591.385 (5)
C18—C191.392 (5)C58—H580.95
C19—C201.393 (5)C59—H590.95
C19—H190.95C61—C661.374 (5)
C20—C211.381 (6)C61—C621.391 (5)
C20—H200.95C62—C631.381 (5)
C21—C221.374 (6)C62—H620.95
C21—H210.95C63—C641.391 (6)
C22—C231.377 (5)C63—H630.95
C22—H220.95C64—C651.374 (6)
C23—H230.95C64—H640.95
C25—C261.378 (5)C65—C661.399 (5)
C25—C301.380 (5)C65—H650.95
C26—C271.392 (5)C66—H660.95
C26—H260.95C67—C721.371 (5)
C27—C281.385 (5)C67—C681.389 (5)
C27—H270.95C68—C691.386 (5)
C28—C291.390 (5)C68—H680.95
C28—H280.95C69—C701.383 (5)
C29—C301.385 (5)C69—H690.95
C29—H290.95C70—C711.383 (5)
C30—H300.95C70—H700.95
C31—C321.381 (5)C71—C721.380 (5)
C31—C361.385 (5)C71—H710.95
C32—C331.380 (5)C72—H720.95
C11—N1—C18122.3 (3)C34—C35—C36120.3 (4)
C11—N1—C12119.8 (2)C34—C35—H35119.8
C18—N1—C12116.1 (2)C36—C35—H35119.8
C24—N2—C31124.9 (3)C31—C36—C35119.7 (4)
C24—N2—C25118.4 (3)C31—C36—H36120.1
C31—N2—C25116.7 (2)C35—C36—H36120.1
C47—N3—C54123.9 (3)C38—C37—C45120.0 (3)
C47—N3—C48118.9 (3)C38—C37—C47118.8 (3)
C54—N3—C48117.0 (3)C45—C37—C47121.0 (3)
C60—N4—C67119.5 (3)C37—C38—C39120.5 (3)
C60—N4—C61120.4 (3)C37—C38—H38119.7
C67—N4—C61119.7 (2)C39—C38—H38119.7
C2—C1—C9119.9 (3)C40—C39—C38121.0 (3)
C2—C1—C11120.8 (3)C40—C39—H39119.5
C9—C1—C11119.2 (3)C38—C39—H39119.5
C1—C2—C3121.0 (3)C39—C40—C46120.0 (3)
C1—C2—H2119.5C39—C40—C60122.5 (3)
C3—C2—H2119.5C46—C40—C60117.5 (3)
C4—C3—C2120.8 (3)C42—C41—C46120.9 (3)
C4—C3—H3119.6C42—C41—H41119.5
C2—C3—H3119.6C46—C41—H41119.5
C3—C4—C10119.5 (3)C41—C42—C43120.3 (4)
C3—C4—C24118.3 (3)C41—C42—H42119.8
C10—C4—C24121.9 (3)C43—C42—H42119.8
C6—C5—C10120.7 (3)C44—C43—C42120.6 (4)
C6—C5—H5119.6C44—C43—H43119.7
C10—C5—H5119.6C42—C43—H43119.7
C5—C6—C7120.7 (3)C43—C44—C45120.3 (3)
C5—C6—H6119.7C43—C44—H44119.8
C7—C6—H6119.7C45—C44—H44119.8
C8—C7—C6120.6 (4)C46—C45—C37119.1 (3)
C8—C7—H7119.7C46—C45—C44118.8 (3)
C6—C7—H7119.7C37—C45—C44122.1 (3)
C7—C8—C9120.4 (3)C45—C46—C41119.0 (3)
C7—C8—H8119.8C45—C46—C40119.4 (3)
C9—C8—H8119.8C41—C46—C40121.6 (3)
C10—C9—C8119.4 (3)O3—C47—N3121.3 (3)
C10—C9—C1118.6 (3)O3—C47—C37121.4 (3)
C8—C9—C1122.0 (3)N3—C47—C37117.2 (3)
C9—C10—C4120.2 (3)C53—C48—C49120.7 (4)
C9—C10—C5118.2 (3)C53—C48—N3119.6 (3)
C4—C10—C5121.7 (3)C49—C48—N3119.7 (3)
O1—C11—N1122.4 (3)C48—C49—C50119.1 (4)
O1—C11—C1120.8 (3)C48—C49—H49120.5
N1—C11—C1116.8 (3)C50—C49—H49120.5
C17—C12—C13119.9 (3)C49—C50—C51120.6 (4)
C17—C12—N1120.6 (3)C49—C50—H50119.7
C13—C12—N1119.3 (3)C51—C50—H50119.7
C14—C13—C12120.4 (3)C52—C51—C50119.4 (4)
C14—C13—H13119.8C52—C51—H51120.3
C12—C13—H13119.8C50—C51—H51120.3
C13—C14—C15120.0 (3)C51—C52—C53120.6 (4)
C13—C14—H14120.0C51—C52—H52119.7
C15—C14—H14120.0C53—C52—H52119.7
C14—C15—C16119.4 (3)C48—C53—C52119.5 (4)
C14—C15—H15120.3C48—C53—H53120.2
C16—C15—H15120.3C52—C53—H53120.2
C17—C16—C15120.6 (3)C55—C54—C59119.3 (3)
C17—C16—H16119.7C55—C54—N3119.5 (3)
C15—C16—H16119.7C59—C54—N3121.1 (3)
C16—C17—C12119.6 (3)C54—C55—C56119.9 (4)
C16—C17—H17120.2C54—C55—H55120.1
C12—C17—H17120.2C56—C55—H55120.1
C23—C18—C19120.2 (3)C57—C56—C55120.9 (4)
C23—C18—N1120.2 (3)C57—C56—H56119.5
C19—C18—N1119.6 (3)C55—C56—H56119.5
C18—C19—C20118.5 (4)C56—C57—C58119.4 (4)
C18—C19—H19120.8C56—C57—H57120.3
C20—C19—H19120.8C58—C57—H57120.3
C21—C20—C19120.8 (4)C57—C58—C59120.2 (4)
C21—C20—H20119.6C57—C58—H58119.9
C19—C20—H20119.6C59—C58—H58119.9
C22—C21—C20119.9 (3)C58—C59—C54120.2 (4)
C22—C21—H21120.1C58—C59—H59119.9
C20—C21—H21120.1C54—C59—H59119.9
C21—C22—C23120.0 (4)O4—C60—N4122.8 (3)
C21—C22—H22120.0O4—C60—C40119.3 (3)
C23—C22—H22120.0N4—C60—C40117.7 (3)
C22—C23—C18120.6 (4)C66—C61—C62120.1 (3)
C22—C23—H23119.7C66—C61—N4121.1 (3)
C18—C23—H23119.7C62—C61—N4118.7 (3)
O2—C24—N2121.5 (3)C63—C62—C61119.7 (4)
O2—C24—C4120.8 (3)C63—C62—H62120.2
N2—C24—C4117.7 (3)C61—C62—H62120.2
C26—C25—C30121.3 (3)C62—C63—C64119.7 (4)
C26—C25—N2119.7 (3)C62—C63—H63120.2
C30—C25—N2119.0 (3)C64—C63—H63120.2
C25—C26—C27119.7 (4)C65—C64—C63121.1 (4)
C25—C26—H26120.2C65—C64—H64119.5
C27—C26—H26120.2C63—C64—H64119.5
C28—C27—C26119.8 (3)C64—C65—C66118.8 (4)
C28—C27—H27120.1C64—C65—H65120.6
C26—C27—H27120.1C66—C65—H65120.6
C27—C28—C29119.6 (4)C61—C66—C65120.6 (4)
C27—C28—H28120.2C61—C66—H66119.7
C29—C28—H28120.2C65—C66—H66119.7
C30—C29—C28120.8 (4)C72—C67—C68120.7 (3)
C30—C29—H29119.6C72—C67—N4120.6 (3)
C28—C29—H29119.6C68—C67—N4118.7 (3)
C25—C30—C29118.8 (3)C69—C68—C67119.1 (3)
C25—C30—H30120.6C69—C68—H68120.5
C29—C30—H30120.6C67—C68—H68120.5
C32—C31—C36119.7 (3)C70—C69—C68120.0 (3)
C32—C31—N2119.2 (3)C70—C69—H69120.0
C36—C31—N2121.1 (3)C68—C69—H69120.0
C33—C32—C31120.1 (4)C69—C70—C71120.5 (3)
C33—C32—H32119.9C69—C70—H70119.7
C31—C32—H32119.9C71—C70—H70119.7
C34—C33—C32120.4 (4)C72—C71—C70119.3 (3)
C34—C33—H33119.8C72—C71—H71120.3
C32—C33—H33119.8C70—C71—H71120.3
C35—C34—C33119.7 (3)C67—C72—C71120.4 (3)
C35—C34—H34120.2C67—C72—H72119.8
C33—C34—H34120.2C71—C72—H72119.8
C9—C1—C2—C31.2 (4)C45—C37—C38—C391.8 (5)
C11—C1—C2—C3175.9 (3)C47—C37—C38—C39172.8 (3)
C1—C2—C3—C40.4 (5)C37—C38—C39—C400.4 (5)
C2—C3—C4—C101.1 (5)C38—C39—C40—C461.8 (5)
C2—C3—C4—C24172.1 (3)C38—C39—C40—C60174.7 (3)
C10—C5—C6—C71.1 (6)C46—C41—C42—C430.4 (5)
C5—C6—C7—C82.0 (6)C41—C42—C43—C440.4 (5)
C6—C7—C8—C90.9 (5)C42—C43—C44—C450.5 (5)
C7—C8—C9—C100.9 (5)C38—C37—C45—C461.1 (4)
C7—C8—C9—C1177.4 (3)C47—C37—C45—C46173.4 (3)
C2—C1—C9—C100.5 (4)C38—C37—C45—C44176.6 (3)
C11—C1—C9—C10176.7 (3)C47—C37—C45—C448.9 (5)
C2—C1—C9—C8177.7 (3)C43—C44—C45—C460.0 (5)
C11—C1—C9—C85.1 (4)C43—C44—C45—C37177.7 (3)
C8—C9—C10—C4179.3 (3)C37—C45—C46—C41178.5 (3)
C1—C9—C10—C41.0 (4)C44—C45—C46—C410.8 (4)
C8—C9—C10—C51.6 (4)C37—C45—C46—C401.0 (4)
C1—C9—C10—C5176.6 (3)C44—C45—C46—C40178.8 (3)
C3—C4—C10—C91.8 (4)C42—C41—C46—C450.9 (5)
C24—C4—C10—C9171.2 (3)C42—C41—C46—C40178.6 (3)
C3—C4—C10—C5175.8 (3)C39—C40—C46—C452.5 (4)
C24—C4—C10—C511.2 (5)C60—C40—C46—C45174.2 (3)
C6—C5—C10—C90.7 (5)C39—C40—C46—C41177.0 (3)
C6—C5—C10—C4178.3 (3)C60—C40—C46—C416.3 (4)
C18—N1—C11—O1173.0 (3)C54—N3—C47—O3159.9 (4)
C12—N1—C11—O18.8 (5)C48—N3—C47—O314.4 (5)
C18—N1—C11—C17.6 (5)C54—N3—C47—C3722.4 (5)
C12—N1—C11—C1171.8 (3)C48—N3—C47—C37163.3 (3)
C2—C1—C11—O1113.1 (4)C38—C37—C47—O3118.5 (4)
C9—C1—C11—O164.1 (4)C45—C37—C47—O356.1 (5)
C2—C1—C11—N166.3 (4)C38—C37—C47—N359.2 (4)
C9—C1—C11—N1116.6 (3)C45—C37—C47—N3126.2 (3)
C11—N1—C12—C17118.4 (3)C47—N3—C48—C53126.1 (4)
C18—N1—C12—C1776.5 (4)C54—N3—C48—C5348.5 (5)
C11—N1—C12—C1366.8 (4)C47—N3—C48—C4955.6 (5)
C18—N1—C12—C1398.3 (3)C54—N3—C48—C49129.8 (4)
C17—C12—C13—C141.1 (5)C53—C48—C49—C500.6 (6)
N1—C12—C13—C14173.8 (3)N3—C48—C49—C50177.7 (3)
C12—C13—C14—C151.5 (5)C48—C49—C50—C510.0 (6)
C13—C14—C15—C162.3 (5)C49—C50—C51—C520.6 (6)
C14—C15—C16—C170.5 (5)C50—C51—C52—C530.6 (6)
C15—C16—C17—C122.0 (5)C49—C48—C53—C520.6 (5)
C13—C12—C17—C162.8 (5)N3—C48—C53—C52177.7 (3)
N1—C12—C17—C16171.9 (3)C51—C52—C53—C480.0 (5)
C11—N1—C18—C2361.9 (5)C47—N3—C54—C55141.9 (4)
C12—N1—C18—C23102.8 (4)C48—N3—C54—C5543.7 (5)
C11—N1—C18—C19118.8 (4)C47—N3—C54—C5940.9 (5)
C12—N1—C18—C1976.4 (4)C48—N3—C54—C59133.5 (4)
C23—C18—C19—C200.9 (5)C59—C54—C55—C561.3 (5)
N1—C18—C19—C20178.4 (3)N3—C54—C55—C56175.9 (3)
C18—C19—C20—C212.5 (6)C54—C55—C56—C572.2 (6)
C19—C20—C21—C222.5 (6)C55—C56—C57—C581.0 (6)
C20—C21—C22—C230.7 (6)C56—C57—C58—C591.0 (6)
C21—C22—C23—C181.0 (6)C57—C58—C59—C541.9 (6)
C19—C18—C23—C220.9 (6)C55—C54—C59—C580.7 (5)
N1—C18—C23—C22179.9 (3)N3—C54—C59—C58177.9 (3)
C31—N2—C24—O2166.9 (3)C67—N4—C60—O4165.4 (3)
C25—N2—C24—O213.4 (5)C61—N4—C60—O47.8 (5)
C31—N2—C24—C415.2 (5)C67—N4—C60—C4019.8 (5)
C25—N2—C24—C4164.6 (3)C61—N4—C60—C40167.0 (3)
C3—C4—C24—O2116.2 (4)C39—C40—C60—O491.3 (4)
C10—C4—C24—O256.9 (5)C46—C40—C60—O485.3 (4)
C3—C4—C24—N261.8 (4)C39—C40—C60—N493.7 (4)
C10—C4—C24—N2125.1 (4)C46—C40—C60—N489.7 (4)
C24—N2—C25—C26119.6 (4)C60—N4—C61—C66126.6 (4)
C31—N2—C25—C2660.6 (4)C67—N4—C61—C6646.6 (5)
C24—N2—C25—C3061.7 (4)C60—N4—C61—C6253.7 (5)
C31—N2—C25—C30118.0 (3)C67—N4—C61—C62133.1 (4)
C30—C25—C26—C270.5 (5)C66—C61—C62—C631.1 (6)
N2—C25—C26—C27179.1 (3)N4—C61—C62—C63179.2 (3)
C25—C26—C27—C280.4 (5)C61—C62—C63—C642.5 (6)
C26—C27—C28—C291.0 (5)C62—C63—C64—C652.6 (6)
C27—C28—C29—C300.8 (5)C63—C64—C65—C661.4 (6)
C26—C25—C30—C290.7 (5)C62—C61—C66—C650.1 (6)
N2—C25—C30—C29179.3 (3)N4—C61—C66—C65179.6 (3)
C28—C29—C30—C250.1 (5)C64—C65—C66—C610.0 (6)
C24—N2—C31—C32138.0 (4)C60—N4—C67—C7291.8 (4)
C25—N2—C31—C3241.7 (4)C61—N4—C67—C7294.9 (4)
C24—N2—C31—C3644.5 (5)C60—N4—C67—C6887.6 (4)
C25—N2—C31—C36135.8 (3)C61—N4—C67—C6885.7 (4)
C36—C31—C32—C330.3 (5)C72—C67—C68—C690.4 (5)
N2—C31—C32—C33177.2 (3)N4—C67—C68—C69179.9 (3)
C31—C32—C33—C341.9 (6)C67—C68—C69—C701.7 (5)
C32—C33—C34—C351.5 (6)C68—C69—C70—C711.4 (6)
C33—C34—C35—C360.4 (6)C69—C70—C71—C720.4 (6)
C32—C31—C36—C351.6 (5)C68—C67—C72—C711.3 (5)
N2—C31—C36—C35179.1 (3)N4—C67—C72—C71178.1 (3)
C34—C35—C36—C312.0 (5)C70—C71—C72—C671.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.952.413.342 (4)166
C30—H30···O1ii0.952.483.413 (4)168
C65—H65···O3iii0.952.593.420 (4)146
C42—H42···O4iv0.952.513.105 (4)120
C68—H68···O4v0.952.353.209 (4)150
C16—H16···Cg2vi0.952.853.443 (1)122
C21—H21···Cg40.952.903.643 (1)135
C39—H39···Cg4vii0.952.863.430 (1)119
C44—H44···Cg3vi0.952.903.600 (1)132
C69—H69···Cg2viii0.952.873.711 (4)148
C71—H71···Cg10.952.913.670 (1)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x1, y+1, z; (iv) x+2, y+1, z+2; (v) x+1, y+1, z+2; (vi) x+1, y1, z; (vii) x+1, y+2, z+2; (viii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC36H26N2O2
Mr518.59
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)10.0276 (8), 13.4211 (11), 20.2414 (13)
α, β, γ (°)88.560 (2), 89.279 (2), 74.523 (3)
V3)2624.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.49 × 0.28 × 0.21
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20350, 9674, 5904
Rint0.055
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.192, 1.00
No. of reflections9674
No. of parameters722
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.69, 0.40

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
C14—H14···O1i0.952.413.342 (4)166
C30—H30···O1ii0.952.483.413 (4)168
C65—H65···O3iii0.952.593.420 (4)146
C42—H42···O4iv0.952.513.105 (4)120
C68—H68···O4v0.952.353.209 (4)150
C16—H16···Cg2vi0.952.853.443 (1)122
C21—H21···Cg40.952.903.643 (1)135
C39—H39···Cg4vii0.952.863.430 (1)119
C44—H44···Cg3vi0.952.903.600 (1)132
C69—H69···Cg2viii0.952.873.711 (4)148
C71—H71···Cg10.952.913.670 (1)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x1, y+1, z; (iv) x+2, y+1, z+2; (v) x+1, y+1, z+2; (vi) x+1, y1, z; (vii) x+1, y+2, z+2; (viii) x, y1, z.
 

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