Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051495/ci2483sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051495/ci2483Isup2.hkl |
CCDC reference: 667427
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (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
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.
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).
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).
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).
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. |
C36H26N2O2 | Z = 4 |
Mr = 518.59 | F(000) = 1088 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0276 (8) Å | Cell parameters from 13361 reflections |
b = 13.4211 (11) Å | θ = 3.0–27.5° |
c = 20.2414 (13) Å | µ = 0.08 mm−1 |
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 |
Rigaku R-AXIS RAPID diffractometer | 5904 reflections with I > 2σ(I) |
Radiation source: Rotating anode | Rint = 0.055 |
Graphite monochromator | θmax = 25.5°, θmin = 3.0° |
ω scans | h = −12→12 |
20350 measured reflections | k = −16→16 |
9674 independent reflections | l = −24→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-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 reflections | Δρmax = 0.69 e Å−3 |
722 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0062 (8) |
C36H26N2O2 | γ = 74.523 (3)° |
Mr = 518.59 | V = 2624.5 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.0276 (8) Å | Mo Kα radiation |
b = 13.4211 (11) Å | µ = 0.08 mm−1 |
c = 20.2414 (13) Å | T = 153 K |
α = 88.560 (2)° | 0.49 × 0.28 × 0.21 mm |
β = 89.279 (2)° |
Rigaku R-AXIS RAPID diffractometer | 5904 reflections with I > 2σ(I) |
20350 measured reflections | Rint = 0.055 |
9674 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.69 e Å−3 |
9674 reflections | Δρmin = −0.40 e Å−3 |
722 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5048 (2) | 0.74330 (18) | 0.48167 (10) | 0.0295 (5) | |
O2 | 0.1292 (3) | 1.2351 (2) | 0.56123 (12) | 0.0428 (7) | |
O3 | 1.0879 (3) | 0.0431 (2) | 0.93001 (12) | 0.0415 (7) | |
O4 | 0.6618 (3) | 0.5119 (2) | 1.01899 (11) | 0.0357 (6) | |
N1 | 0.6095 (3) | 0.7125 (2) | 0.58195 (12) | 0.0269 (6) | |
N2 | 0.2346 (3) | 1.2341 (2) | 0.65984 (13) | 0.0303 (7) | |
N3 | 0.9590 (3) | 0.0321 (2) | 0.84020 (13) | 0.0325 (7) | |
N4 | 0.6043 (3) | 0.5654 (2) | 0.91324 (12) | 0.0273 (6) | |
C1 | 0.4381 (3) | 0.8770 (3) | 0.55987 (14) | 0.0264 (7) | |
C2 | 0.5034 (3) | 0.9527 (2) | 0.57279 (14) | 0.0241 (7) | |
H2 | 0.6015 | 0.9368 | 0.5703 | 0.029* | |
C3 | 0.4280 (3) | 1.0518 (3) | 0.58946 (14) | 0.0281 (8) | |
H3 | 0.4751 | 1.1029 | 0.5979 | 0.034* | |
C4 | 0.2851 (3) | 1.0769 (3) | 0.59392 (15) | 0.0283 (8) | |
C5 | 0.0682 (4) | 1.0197 (3) | 0.59077 (17) | 0.0382 (9) | |
H5 | 0.0153 | 1.0866 | 0.6031 | 0.046* | |
C6 | 0.0036 (4) | 0.9439 (3) | 0.58117 (18) | 0.0402 (9) | |
H6 | −0.0936 | 0.9581 | 0.5877 | 0.048* | |
C7 | 0.0786 (4) | 0.8459 (3) | 0.56193 (18) | 0.0411 (9) | |
H7 | 0.0317 | 0.7945 | 0.5541 | 0.049* | |
C8 | 0.2189 (4) | 0.8230 (3) | 0.55423 (16) | 0.0334 (8) | |
H8 | 0.2690 | 0.7555 | 0.5417 | 0.040* | |
C9 | 0.2905 (3) | 0.8995 (3) | 0.56481 (14) | 0.0258 (7) | |
C10 | 0.2151 (3) | 0.9997 (3) | 0.58244 (15) | 0.0276 (7) | |
C11 | 0.5192 (3) | 0.7723 (3) | 0.53754 (15) | 0.0251 (7) | |
C12 | 0.6774 (3) | 0.6061 (3) | 0.56730 (14) | 0.0247 (7) | |
C13 | 0.5991 (3) | 0.5355 (3) | 0.56387 (15) | 0.0276 (7) | |
H13 | 0.5011 | 0.5587 | 0.5667 | 0.033* | |
C14 | 0.6627 (4) | 0.4318 (3) | 0.55629 (15) | 0.0318 (8) | |
H14 | 0.6084 | 0.3840 | 0.5529 | 0.038* | |
C15 | 0.8050 (4) | 0.3975 (3) | 0.55365 (15) | 0.0310 (8) | |
H15 | 0.8493 | 0.3258 | 0.5501 | 0.037* | |
C16 | 0.8833 (4) | 0.4686 (3) | 0.55627 (16) | 0.0316 (8) | |
H16 | 0.9813 | 0.4453 | 0.5541 | 0.038* | |
C17 | 0.8197 (3) | 0.5728 (3) | 0.56202 (15) | 0.0302 (8) | |
H17 | 0.8736 | 0.6212 | 0.5624 | 0.036* | |
C18 | 0.6154 (4) | 0.7416 (3) | 0.64971 (15) | 0.0287 (8) | |
C19 | 0.7372 (4) | 0.7577 (3) | 0.67385 (18) | 0.0357 (9) | |
H19 | 0.8157 | 0.7515 | 0.6459 | 0.043* | |
C20 | 0.7414 (4) | 0.7832 (3) | 0.73996 (19) | 0.0457 (11) | |
H20 | 0.8248 | 0.7917 | 0.7577 | 0.055* | |
C21 | 0.6258 (5) | 0.7962 (3) | 0.77997 (18) | 0.0459 (11) | |
H21 | 0.6288 | 0.8162 | 0.8245 | 0.055* | |
C22 | 0.5064 (4) | 0.7801 (3) | 0.75530 (17) | 0.0407 (9) | |
H22 | 0.4271 | 0.7883 | 0.7829 | 0.049* | |
C23 | 0.5018 (4) | 0.7522 (3) | 0.69054 (16) | 0.0357 (9) | |
H23 | 0.4194 | 0.7402 | 0.6739 | 0.043* | |
C24 | 0.2087 (4) | 1.1875 (3) | 0.60324 (16) | 0.0311 (8) | |
C25 | 0.1900 (3) | 1.3461 (3) | 0.66238 (15) | 0.0271 (7) | |
C26 | 0.0965 (3) | 1.3928 (3) | 0.71010 (16) | 0.0313 (8) | |
H26 | 0.0604 | 1.3519 | 0.7408 | 0.038* | |
C27 | 0.0553 (4) | 1.5001 (3) | 0.71307 (17) | 0.0360 (9) | |
H27 | −0.0087 | 1.5328 | 0.7460 | 0.043* | |
C28 | 0.1079 (4) | 1.5592 (3) | 0.66786 (17) | 0.0359 (9) | |
H28 | 0.0790 | 1.6326 | 0.6692 | 0.043* | |
C29 | 0.2031 (4) | 1.5105 (3) | 0.62054 (16) | 0.0331 (8) | |
H29 | 0.2401 | 1.5510 | 0.5899 | 0.040* | |
C30 | 0.2449 (4) | 1.4037 (3) | 0.61751 (16) | 0.0318 (8) | |
H30 | 0.3100 | 1.3706 | 0.5851 | 0.038* | |
C31 | 0.3036 (4) | 1.1801 (3) | 0.71727 (15) | 0.0296 (8) | |
C32 | 0.3998 (4) | 1.2187 (3) | 0.74882 (17) | 0.0341 (8) | |
H32 | 0.4226 | 1.2784 | 0.7314 | 0.041* | |
C33 | 0.4629 (4) | 1.1706 (3) | 0.80566 (18) | 0.0413 (10) | |
H33 | 0.5270 | 1.1986 | 0.8279 | 0.050* | |
C34 | 0.4336 (4) | 1.0820 (3) | 0.83032 (17) | 0.0442 (10) | |
H34 | 0.4789 | 1.0482 | 0.8688 | 0.053* | |
C35 | 0.3383 (4) | 1.0429 (3) | 0.79884 (17) | 0.0401 (9) | |
H35 | 0.3183 | 0.9817 | 0.8156 | 0.048* | |
C36 | 0.2712 (4) | 1.0926 (3) | 0.74273 (16) | 0.0350 (8) | |
H36 | 0.2033 | 1.0667 | 0.7219 | 0.042* | |
C37 | 0.9085 (4) | 0.1931 (3) | 0.90240 (15) | 0.0282 (8) | |
C38 | 0.7680 (4) | 0.2105 (3) | 0.91349 (16) | 0.0319 (8) | |
H38 | 0.7259 | 0.1554 | 0.9096 | 0.038* | |
C39 | 0.6872 (4) | 0.3090 (3) | 0.93039 (15) | 0.0286 (7) | |
H39 | 0.5908 | 0.3196 | 0.9381 | 0.034* | |
C40 | 0.7443 (4) | 0.3892 (3) | 0.93589 (15) | 0.0284 (8) | |
C41 | 0.9507 (4) | 0.4578 (3) | 0.92473 (16) | 0.0333 (8) | |
H41 | 0.8961 | 0.5245 | 0.9363 | 0.040* | |
C42 | 1.0879 (4) | 0.4434 (3) | 0.91044 (17) | 0.0382 (9) | |
H42 | 1.1277 | 0.5001 | 0.9119 | 0.046* | |
C43 | 1.1698 (4) | 0.3458 (3) | 0.89371 (17) | 0.0368 (9) | |
H43 | 1.2651 | 0.3366 | 0.8836 | 0.044* | |
C44 | 1.1141 (4) | 0.2630 (3) | 0.89171 (17) | 0.0358 (9) | |
H44 | 1.1711 | 0.1968 | 0.8806 | 0.043* | |
C45 | 0.9712 (3) | 0.2758 (3) | 0.90621 (15) | 0.0293 (8) | |
C46 | 0.8887 (3) | 0.3748 (3) | 0.92251 (15) | 0.0263 (7) | |
C47 | 0.9939 (4) | 0.0847 (3) | 0.89241 (16) | 0.0318 (8) | |
C48 | 1.0115 (4) | −0.0788 (3) | 0.83908 (17) | 0.0320 (8) | |
C49 | 0.9870 (4) | −0.1382 (3) | 0.89221 (19) | 0.0435 (10) | |
H49 | 0.9387 | −0.1063 | 0.9301 | 0.052* | |
C50 | 1.0338 (5) | −0.2450 (3) | 0.8895 (2) | 0.0502 (11) | |
H50 | 1.0174 | −0.2865 | 0.9258 | 0.060* | |
C51 | 1.1044 (4) | −0.2920 (3) | 0.8341 (2) | 0.0471 (11) | |
H51 | 1.1355 | −0.3652 | 0.8324 | 0.057* | |
C52 | 1.1289 (4) | −0.2318 (3) | 0.7823 (2) | 0.0428 (10) | |
H52 | 1.1780 | −0.2636 | 0.7445 | 0.051* | |
C53 | 1.0827 (4) | −0.1246 (3) | 0.78424 (18) | 0.0366 (9) | |
H53 | 1.1000 | −0.0832 | 0.7480 | 0.044* | |
C54 | 0.8826 (4) | 0.0821 (3) | 0.78338 (16) | 0.0306 (8) | |
C55 | 0.7856 (4) | 0.0398 (3) | 0.75558 (18) | 0.0390 (9) | |
H55 | 0.7654 | −0.0193 | 0.7756 | 0.047* | |
C56 | 0.7179 (4) | 0.0837 (3) | 0.69838 (19) | 0.0449 (10) | |
H56 | 0.6536 | 0.0529 | 0.6786 | 0.054* | |
C57 | 0.7423 (4) | 0.1711 (3) | 0.66984 (18) | 0.0440 (10) | |
H57 | 0.6943 | 0.2013 | 0.6310 | 0.053* | |
C58 | 0.8375 (4) | 0.2149 (3) | 0.69816 (17) | 0.0422 (10) | |
H58 | 0.8539 | 0.2760 | 0.6791 | 0.051* | |
C59 | 0.9090 (4) | 0.1698 (3) | 0.75415 (16) | 0.0354 (8) | |
H59 | 0.9763 | 0.1990 | 0.7726 | 0.042* | |
C60 | 0.6635 (3) | 0.4933 (3) | 0.95938 (15) | 0.0264 (7) | |
C61 | 0.5503 (4) | 0.6726 (3) | 0.93096 (15) | 0.0303 (8) | |
C62 | 0.6368 (4) | 0.7212 (3) | 0.96301 (18) | 0.0401 (9) | |
H62 | 0.7298 | 0.6845 | 0.9724 | 0.048* | |
C63 | 0.5869 (4) | 0.8231 (3) | 0.98110 (19) | 0.0466 (10) | |
H63 | 0.6442 | 0.8559 | 1.0045 | 0.056* | |
C64 | 0.4523 (5) | 0.8772 (3) | 0.96485 (19) | 0.0473 (10) | |
H64 | 0.4196 | 0.9481 | 0.9757 | 0.057* | |
C65 | 0.3659 (4) | 0.8300 (3) | 0.93334 (17) | 0.0396 (9) | |
H65 | 0.2735 | 0.8671 | 0.9233 | 0.048* | |
C66 | 0.4166 (4) | 0.7262 (3) | 0.91635 (16) | 0.0367 (9) | |
H66 | 0.3580 | 0.6926 | 0.8945 | 0.044* | |
C67 | 0.5813 (3) | 0.5334 (3) | 0.84756 (15) | 0.0287 (8) | |
C68 | 0.4591 (4) | 0.5074 (3) | 0.83508 (16) | 0.0312 (8) | |
H68 | 0.3919 | 0.5108 | 0.8691 | 0.037* | |
C69 | 0.4365 (4) | 0.4764 (3) | 0.77233 (16) | 0.0366 (9) | |
H69 | 0.3522 | 0.4603 | 0.7627 | 0.044* | |
C70 | 0.5365 (4) | 0.4691 (3) | 0.72372 (16) | 0.0344 (8) | |
H70 | 0.5215 | 0.4465 | 0.6810 | 0.041* | |
C71 | 0.6583 (4) | 0.4945 (3) | 0.73674 (16) | 0.0339 (8) | |
H71 | 0.7271 | 0.4890 | 0.7033 | 0.041* | |
C72 | 0.6790 (3) | 0.5279 (3) | 0.79878 (15) | 0.0305 (8) | |
H72 | 0.7613 | 0.5473 | 0.8077 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0352 (13) | 0.0278 (14) | 0.0258 (11) | −0.0084 (11) | −0.0037 (10) | −0.0024 (9) |
O2 | 0.0499 (16) | 0.0291 (15) | 0.0441 (14) | 0.0003 (12) | −0.0239 (12) | −0.0042 (11) |
O3 | 0.0469 (16) | 0.0324 (15) | 0.0421 (14) | −0.0042 (12) | −0.0173 (12) | −0.0016 (11) |
O4 | 0.0434 (15) | 0.0360 (15) | 0.0267 (12) | −0.0084 (12) | −0.0033 (10) | −0.0026 (10) |
N1 | 0.0333 (15) | 0.0216 (15) | 0.0247 (13) | −0.0053 (12) | −0.0043 (11) | −0.0032 (11) |
N2 | 0.0355 (16) | 0.0246 (16) | 0.0263 (14) | 0.0006 (13) | −0.0073 (12) | −0.0042 (11) |
N3 | 0.0390 (17) | 0.0250 (16) | 0.0315 (15) | −0.0045 (13) | −0.0083 (12) | −0.0021 (12) |
N4 | 0.0310 (15) | 0.0230 (15) | 0.0252 (13) | −0.0021 (12) | −0.0020 (11) | −0.0026 (11) |
C1 | 0.0306 (17) | 0.0285 (19) | 0.0188 (14) | −0.0054 (15) | −0.0056 (13) | −0.0014 (13) |
C2 | 0.0245 (16) | 0.0235 (18) | 0.0255 (15) | −0.0083 (14) | −0.0033 (12) | −0.0004 (13) |
C3 | 0.0350 (19) | 0.0269 (19) | 0.0218 (15) | −0.0066 (15) | −0.0063 (13) | −0.0017 (13) |
C4 | 0.0318 (18) | 0.0265 (19) | 0.0241 (15) | −0.0030 (15) | −0.0042 (13) | −0.0049 (13) |
C5 | 0.034 (2) | 0.039 (2) | 0.0400 (19) | −0.0044 (17) | −0.0075 (16) | −0.0097 (16) |
C6 | 0.0259 (18) | 0.049 (3) | 0.048 (2) | −0.0133 (18) | 0.0043 (16) | −0.0138 (18) |
C7 | 0.037 (2) | 0.043 (2) | 0.046 (2) | −0.0137 (18) | −0.0043 (17) | −0.0109 (18) |
C8 | 0.036 (2) | 0.030 (2) | 0.0363 (18) | −0.0128 (16) | −0.0035 (15) | −0.0061 (15) |
C9 | 0.0298 (17) | 0.0253 (18) | 0.0228 (15) | −0.0077 (14) | −0.0010 (13) | −0.0035 (13) |
C10 | 0.0332 (18) | 0.0242 (18) | 0.0263 (16) | −0.0086 (15) | −0.0064 (13) | −0.0034 (13) |
C11 | 0.0266 (17) | 0.0245 (18) | 0.0265 (16) | −0.0108 (14) | −0.0024 (13) | 0.0002 (13) |
C12 | 0.0261 (17) | 0.0267 (18) | 0.0212 (14) | −0.0066 (14) | −0.0021 (12) | −0.0012 (13) |
C13 | 0.0286 (17) | 0.0280 (19) | 0.0289 (16) | −0.0120 (15) | −0.0036 (13) | −0.0004 (13) |
C14 | 0.040 (2) | 0.029 (2) | 0.0279 (16) | −0.0100 (16) | −0.0066 (15) | −0.0020 (14) |
C15 | 0.043 (2) | 0.0256 (19) | 0.0234 (16) | −0.0065 (16) | −0.0067 (14) | 0.0008 (13) |
C16 | 0.0263 (17) | 0.035 (2) | 0.0328 (17) | −0.0057 (15) | −0.0033 (14) | −0.0063 (15) |
C17 | 0.0285 (18) | 0.032 (2) | 0.0308 (17) | −0.0091 (15) | −0.0029 (14) | −0.0033 (14) |
C18 | 0.0342 (19) | 0.0230 (18) | 0.0269 (16) | −0.0039 (15) | −0.0034 (14) | −0.0021 (13) |
C19 | 0.0339 (19) | 0.033 (2) | 0.0414 (19) | −0.0101 (17) | −0.0071 (16) | −0.0037 (16) |
C20 | 0.052 (3) | 0.037 (2) | 0.048 (2) | −0.0094 (19) | −0.023 (2) | −0.0064 (18) |
C21 | 0.075 (3) | 0.033 (2) | 0.0285 (18) | −0.011 (2) | −0.0094 (19) | −0.0004 (15) |
C22 | 0.056 (2) | 0.036 (2) | 0.0288 (18) | −0.0096 (19) | 0.0009 (17) | 0.0021 (15) |
C23 | 0.043 (2) | 0.034 (2) | 0.0298 (17) | −0.0101 (17) | −0.0028 (15) | 0.0023 (15) |
C24 | 0.0311 (18) | 0.028 (2) | 0.0314 (17) | −0.0037 (15) | −0.0038 (14) | −0.0038 (14) |
C25 | 0.0287 (17) | 0.0221 (18) | 0.0261 (16) | 0.0012 (14) | −0.0042 (13) | −0.0062 (13) |
C26 | 0.0310 (18) | 0.032 (2) | 0.0320 (17) | −0.0108 (16) | 0.0018 (14) | −0.0030 (14) |
C27 | 0.035 (2) | 0.032 (2) | 0.0389 (19) | −0.0050 (17) | −0.0033 (15) | −0.0088 (16) |
C28 | 0.039 (2) | 0.029 (2) | 0.0383 (19) | −0.0045 (16) | −0.0128 (16) | −0.0024 (15) |
C29 | 0.038 (2) | 0.034 (2) | 0.0297 (17) | −0.0129 (16) | −0.0082 (15) | 0.0013 (14) |
C30 | 0.0341 (19) | 0.034 (2) | 0.0250 (16) | −0.0043 (16) | −0.0048 (14) | −0.0046 (14) |
C31 | 0.0354 (19) | 0.0242 (19) | 0.0258 (16) | −0.0018 (15) | −0.0034 (14) | −0.0036 (13) |
C32 | 0.0349 (19) | 0.032 (2) | 0.0360 (18) | −0.0098 (16) | −0.0055 (15) | −0.0032 (15) |
C33 | 0.039 (2) | 0.043 (2) | 0.040 (2) | −0.0054 (18) | −0.0110 (17) | −0.0056 (17) |
C34 | 0.045 (2) | 0.050 (3) | 0.0291 (18) | 0.001 (2) | −0.0053 (16) | 0.0009 (17) |
C35 | 0.051 (2) | 0.032 (2) | 0.0330 (18) | −0.0039 (18) | 0.0045 (17) | 0.0033 (15) |
C36 | 0.042 (2) | 0.032 (2) | 0.0305 (17) | −0.0085 (17) | 0.0020 (15) | −0.0042 (15) |
C37 | 0.0358 (19) | 0.0222 (18) | 0.0270 (16) | −0.0080 (15) | −0.0070 (14) | −0.0008 (13) |
C38 | 0.0339 (19) | 0.031 (2) | 0.0316 (17) | −0.0104 (16) | −0.0059 (14) | −0.0012 (14) |
C39 | 0.0284 (17) | 0.0279 (19) | 0.0290 (16) | −0.0064 (15) | −0.0015 (13) | −0.0026 (14) |
C40 | 0.0363 (19) | 0.0254 (19) | 0.0231 (15) | −0.0071 (15) | −0.0046 (13) | −0.0002 (13) |
C41 | 0.036 (2) | 0.030 (2) | 0.0344 (18) | −0.0100 (16) | 0.0013 (15) | −0.0049 (15) |
C42 | 0.040 (2) | 0.038 (2) | 0.0386 (19) | −0.0127 (18) | −0.0020 (16) | −0.0054 (16) |
C43 | 0.0300 (19) | 0.040 (2) | 0.0419 (19) | −0.0118 (17) | 0.0018 (15) | −0.0087 (16) |
C44 | 0.0335 (19) | 0.038 (2) | 0.0343 (18) | −0.0063 (17) | −0.0005 (15) | −0.0094 (15) |
C45 | 0.0319 (18) | 0.032 (2) | 0.0236 (15) | −0.0080 (15) | −0.0061 (13) | −0.0008 (13) |
C46 | 0.0300 (17) | 0.0250 (18) | 0.0246 (15) | −0.0084 (14) | −0.0002 (13) | −0.0035 (13) |
C47 | 0.0348 (19) | 0.031 (2) | 0.0303 (17) | −0.0088 (16) | −0.0030 (15) | 0.0001 (14) |
C48 | 0.0331 (19) | 0.0235 (19) | 0.0377 (18) | −0.0039 (15) | −0.0095 (15) | −0.0041 (14) |
C49 | 0.049 (2) | 0.033 (2) | 0.047 (2) | −0.0103 (19) | −0.0019 (18) | 0.0002 (17) |
C50 | 0.060 (3) | 0.028 (2) | 0.062 (3) | −0.012 (2) | −0.007 (2) | 0.0086 (19) |
C51 | 0.044 (2) | 0.030 (2) | 0.066 (3) | −0.0063 (18) | −0.018 (2) | −0.0011 (19) |
C52 | 0.037 (2) | 0.033 (2) | 0.057 (2) | −0.0049 (18) | −0.0097 (18) | −0.0138 (18) |
C53 | 0.040 (2) | 0.031 (2) | 0.0402 (19) | −0.0112 (17) | −0.0022 (16) | −0.0057 (16) |
C54 | 0.0345 (19) | 0.0255 (19) | 0.0291 (16) | −0.0032 (15) | −0.0034 (14) | −0.0027 (14) |
C55 | 0.0325 (19) | 0.040 (2) | 0.047 (2) | −0.0126 (17) | −0.0077 (16) | −0.0055 (17) |
C56 | 0.038 (2) | 0.050 (3) | 0.043 (2) | −0.0035 (19) | −0.0108 (17) | −0.0074 (19) |
C57 | 0.043 (2) | 0.046 (3) | 0.0327 (19) | 0.0059 (19) | −0.0048 (16) | −0.0017 (17) |
C58 | 0.051 (2) | 0.038 (2) | 0.0342 (19) | −0.0066 (19) | −0.0038 (17) | 0.0020 (16) |
C59 | 0.045 (2) | 0.029 (2) | 0.0321 (18) | −0.0085 (17) | −0.0023 (15) | −0.0024 (15) |
C60 | 0.0279 (17) | 0.0234 (18) | 0.0289 (16) | −0.0085 (14) | −0.0027 (13) | −0.0014 (13) |
C61 | 0.0332 (18) | 0.033 (2) | 0.0229 (15) | −0.0055 (16) | −0.0010 (13) | −0.0026 (14) |
C62 | 0.040 (2) | 0.032 (2) | 0.046 (2) | −0.0035 (17) | −0.0046 (17) | −0.0073 (16) |
C63 | 0.053 (3) | 0.040 (2) | 0.047 (2) | −0.011 (2) | −0.0046 (19) | −0.0082 (18) |
C64 | 0.066 (3) | 0.031 (2) | 0.044 (2) | −0.012 (2) | 0.002 (2) | 0.0001 (17) |
C65 | 0.046 (2) | 0.033 (2) | 0.0309 (18) | 0.0055 (18) | −0.0064 (16) | 0.0007 (15) |
C66 | 0.042 (2) | 0.033 (2) | 0.0320 (18) | −0.0041 (17) | −0.0082 (16) | −0.0052 (15) |
C67 | 0.0323 (18) | 0.0285 (19) | 0.0219 (15) | −0.0019 (15) | −0.0055 (13) | −0.0012 (13) |
C68 | 0.0327 (18) | 0.032 (2) | 0.0294 (17) | −0.0097 (16) | 0.0000 (14) | −0.0015 (14) |
C69 | 0.039 (2) | 0.040 (2) | 0.0314 (17) | −0.0109 (18) | −0.0065 (15) | −0.0031 (16) |
C70 | 0.045 (2) | 0.037 (2) | 0.0238 (16) | −0.0161 (17) | −0.0034 (15) | −0.0032 (14) |
C71 | 0.039 (2) | 0.034 (2) | 0.0275 (17) | −0.0089 (17) | 0.0013 (15) | −0.0001 (14) |
C72 | 0.0271 (17) | 0.036 (2) | 0.0286 (16) | −0.0086 (16) | 0.0008 (13) | −0.0012 (14) |
O1—C11 | 1.228 (4) | C32—H32 | 0.95 |
O2—C24 | 1.219 (4) | C33—C34 | 1.379 (6) |
O3—C47 | 1.223 (4) | C33—H33 | 0.95 |
O4—C60 | 1.237 (4) | C34—C35 | 1.376 (6) |
N1—C11 | 1.366 (4) | C34—H34 | 0.95 |
N1—C18 | 1.442 (4) | C35—C36 | 1.389 (5) |
N1—C12 | 1.446 (4) | C35—H35 | 0.95 |
N2—C24 | 1.379 (4) | C36—H36 | 0.95 |
N2—C31 | 1.437 (4) | C37—C38 | 1.382 (5) |
N2—C25 | 1.452 (4) | C37—C45 | 1.418 (5) |
N3—C47 | 1.384 (4) | C37—C47 | 1.495 (5) |
N3—C54 | 1.438 (4) | C38—C39 | 1.401 (5) |
N3—C48 | 1.441 (4) | C38—H38 | 0.95 |
N4—C60 | 1.350 (4) | C39—C40 | 1.356 (5) |
N4—C67 | 1.447 (4) | C39—H39 | 0.95 |
N4—C61 | 1.449 (4) | C40—C46 | 1.432 (5) |
C1—C2 | 1.379 (5) | C40—C60 | 1.501 (5) |
C1—C9 | 1.433 (5) | C41—C42 | 1.365 (5) |
C1—C11 | 1.501 (4) | C41—C46 | 1.415 (5) |
C2—C3 | 1.391 (4) | C41—H41 | 0.95 |
C2—H2 | 0.95 | C42—C43 | 1.395 (5) |
C3—C4 | 1.384 (5) | C42—H42 | 0.95 |
C3—H3 | 0.95 | C43—C44 | 1.373 (5) |
C4—C10 | 1.423 (5) | C43—H43 | 0.95 |
C4—C24 | 1.493 (5) | C44—C45 | 1.425 (5) |
C5—C6 | 1.363 (5) | C44—H44 | 0.95 |
C5—C10 | 1.433 (5) | C45—C46 | 1.410 (5) |
C5—H5 | 0.95 | C48—C53 | 1.378 (5) |
C6—C7 | 1.392 (5) | C48—C49 | 1.381 (5) |
C6—H6 | 0.95 | C49—C50 | 1.387 (6) |
C7—C8 | 1.365 (5) | C49—H49 | 0.95 |
C7—H7 | 0.95 | C50—C51 | 1.389 (6) |
C8—C9 | 1.422 (5) | C50—H50 | 0.95 |
C8—H8 | 0.95 | C51—C52 | 1.368 (6) |
C9—C10 | 1.408 (4) | C51—H51 | 0.95 |
C12—C17 | 1.381 (5) | C52—C53 | 1.390 (5) |
C12—C13 | 1.385 (5) | C52—H52 | 0.95 |
C13—C14 | 1.378 (5) | C53—H53 | 0.95 |
C13—H13 | 0.95 | C54—C55 | 1.382 (5) |
C14—C15 | 1.379 (5) | C54—C59 | 1.391 (5) |
C14—H14 | 0.95 | C55—C56 | 1.386 (5) |
C15—C16 | 1.390 (5) | C55—H55 | 0.95 |
C15—H15 | 0.95 | C56—C57 | 1.373 (6) |
C16—C17 | 1.380 (5) | C56—H56 | 0.95 |
C16—H16 | 0.95 | C57—C58 | 1.384 (6) |
C17—H17 | 0.95 | C57—H57 | 0.95 |
C18—C23 | 1.378 (5) | C58—C59 | 1.385 (5) |
C18—C19 | 1.392 (5) | C58—H58 | 0.95 |
C19—C20 | 1.393 (5) | C59—H59 | 0.95 |
C19—H19 | 0.95 | C61—C66 | 1.374 (5) |
C20—C21 | 1.381 (6) | C61—C62 | 1.391 (5) |
C20—H20 | 0.95 | C62—C63 | 1.381 (5) |
C21—C22 | 1.374 (6) | C62—H62 | 0.95 |
C21—H21 | 0.95 | C63—C64 | 1.391 (6) |
C22—C23 | 1.377 (5) | C63—H63 | 0.95 |
C22—H22 | 0.95 | C64—C65 | 1.374 (6) |
C23—H23 | 0.95 | C64—H64 | 0.95 |
C25—C26 | 1.378 (5) | C65—C66 | 1.399 (5) |
C25—C30 | 1.380 (5) | C65—H65 | 0.95 |
C26—C27 | 1.392 (5) | C66—H66 | 0.95 |
C26—H26 | 0.95 | C67—C72 | 1.371 (5) |
C27—C28 | 1.385 (5) | C67—C68 | 1.389 (5) |
C27—H27 | 0.95 | C68—C69 | 1.386 (5) |
C28—C29 | 1.390 (5) | C68—H68 | 0.95 |
C28—H28 | 0.95 | C69—C70 | 1.383 (5) |
C29—C30 | 1.385 (5) | C69—H69 | 0.95 |
C29—H29 | 0.95 | C70—C71 | 1.383 (5) |
C30—H30 | 0.95 | C70—H70 | 0.95 |
C31—C32 | 1.381 (5) | C71—C72 | 1.380 (5) |
C31—C36 | 1.385 (5) | C71—H71 | 0.95 |
C32—C33 | 1.380 (5) | C72—H72 | 0.95 |
C11—N1—C18 | 122.3 (3) | C34—C35—C36 | 120.3 (4) |
C11—N1—C12 | 119.8 (2) | C34—C35—H35 | 119.8 |
C18—N1—C12 | 116.1 (2) | C36—C35—H35 | 119.8 |
C24—N2—C31 | 124.9 (3) | C31—C36—C35 | 119.7 (4) |
C24—N2—C25 | 118.4 (3) | C31—C36—H36 | 120.1 |
C31—N2—C25 | 116.7 (2) | C35—C36—H36 | 120.1 |
C47—N3—C54 | 123.9 (3) | C38—C37—C45 | 120.0 (3) |
C47—N3—C48 | 118.9 (3) | C38—C37—C47 | 118.8 (3) |
C54—N3—C48 | 117.0 (3) | C45—C37—C47 | 121.0 (3) |
C60—N4—C67 | 119.5 (3) | C37—C38—C39 | 120.5 (3) |
C60—N4—C61 | 120.4 (3) | C37—C38—H38 | 119.7 |
C67—N4—C61 | 119.7 (2) | C39—C38—H38 | 119.7 |
C2—C1—C9 | 119.9 (3) | C40—C39—C38 | 121.0 (3) |
C2—C1—C11 | 120.8 (3) | C40—C39—H39 | 119.5 |
C9—C1—C11 | 119.2 (3) | C38—C39—H39 | 119.5 |
C1—C2—C3 | 121.0 (3) | C39—C40—C46 | 120.0 (3) |
C1—C2—H2 | 119.5 | C39—C40—C60 | 122.5 (3) |
C3—C2—H2 | 119.5 | C46—C40—C60 | 117.5 (3) |
C4—C3—C2 | 120.8 (3) | C42—C41—C46 | 120.9 (3) |
C4—C3—H3 | 119.6 | C42—C41—H41 | 119.5 |
C2—C3—H3 | 119.6 | C46—C41—H41 | 119.5 |
C3—C4—C10 | 119.5 (3) | C41—C42—C43 | 120.3 (4) |
C3—C4—C24 | 118.3 (3) | C41—C42—H42 | 119.8 |
C10—C4—C24 | 121.9 (3) | C43—C42—H42 | 119.8 |
C6—C5—C10 | 120.7 (3) | C44—C43—C42 | 120.6 (4) |
C6—C5—H5 | 119.6 | C44—C43—H43 | 119.7 |
C10—C5—H5 | 119.6 | C42—C43—H43 | 119.7 |
C5—C6—C7 | 120.7 (3) | C43—C44—C45 | 120.3 (3) |
C5—C6—H6 | 119.7 | C43—C44—H44 | 119.8 |
C7—C6—H6 | 119.7 | C45—C44—H44 | 119.8 |
C8—C7—C6 | 120.6 (4) | C46—C45—C37 | 119.1 (3) |
C8—C7—H7 | 119.7 | C46—C45—C44 | 118.8 (3) |
C6—C7—H7 | 119.7 | C37—C45—C44 | 122.1 (3) |
C7—C8—C9 | 120.4 (3) | C45—C46—C41 | 119.0 (3) |
C7—C8—H8 | 119.8 | C45—C46—C40 | 119.4 (3) |
C9—C8—H8 | 119.8 | C41—C46—C40 | 121.6 (3) |
C10—C9—C8 | 119.4 (3) | O3—C47—N3 | 121.3 (3) |
C10—C9—C1 | 118.6 (3) | O3—C47—C37 | 121.4 (3) |
C8—C9—C1 | 122.0 (3) | N3—C47—C37 | 117.2 (3) |
C9—C10—C4 | 120.2 (3) | C53—C48—C49 | 120.7 (4) |
C9—C10—C5 | 118.2 (3) | C53—C48—N3 | 119.6 (3) |
C4—C10—C5 | 121.7 (3) | C49—C48—N3 | 119.7 (3) |
O1—C11—N1 | 122.4 (3) | C48—C49—C50 | 119.1 (4) |
O1—C11—C1 | 120.8 (3) | C48—C49—H49 | 120.5 |
N1—C11—C1 | 116.8 (3) | C50—C49—H49 | 120.5 |
C17—C12—C13 | 119.9 (3) | C49—C50—C51 | 120.6 (4) |
C17—C12—N1 | 120.6 (3) | C49—C50—H50 | 119.7 |
C13—C12—N1 | 119.3 (3) | C51—C50—H50 | 119.7 |
C14—C13—C12 | 120.4 (3) | C52—C51—C50 | 119.4 (4) |
C14—C13—H13 | 119.8 | C52—C51—H51 | 120.3 |
C12—C13—H13 | 119.8 | C50—C51—H51 | 120.3 |
C13—C14—C15 | 120.0 (3) | C51—C52—C53 | 120.6 (4) |
C13—C14—H14 | 120.0 | C51—C52—H52 | 119.7 |
C15—C14—H14 | 120.0 | C53—C52—H52 | 119.7 |
C14—C15—C16 | 119.4 (3) | C48—C53—C52 | 119.5 (4) |
C14—C15—H15 | 120.3 | C48—C53—H53 | 120.2 |
C16—C15—H15 | 120.3 | C52—C53—H53 | 120.2 |
C17—C16—C15 | 120.6 (3) | C55—C54—C59 | 119.3 (3) |
C17—C16—H16 | 119.7 | C55—C54—N3 | 119.5 (3) |
C15—C16—H16 | 119.7 | C59—C54—N3 | 121.1 (3) |
C16—C17—C12 | 119.6 (3) | C54—C55—C56 | 119.9 (4) |
C16—C17—H17 | 120.2 | C54—C55—H55 | 120.1 |
C12—C17—H17 | 120.2 | C56—C55—H55 | 120.1 |
C23—C18—C19 | 120.2 (3) | C57—C56—C55 | 120.9 (4) |
C23—C18—N1 | 120.2 (3) | C57—C56—H56 | 119.5 |
C19—C18—N1 | 119.6 (3) | C55—C56—H56 | 119.5 |
C18—C19—C20 | 118.5 (4) | C56—C57—C58 | 119.4 (4) |
C18—C19—H19 | 120.8 | C56—C57—H57 | 120.3 |
C20—C19—H19 | 120.8 | C58—C57—H57 | 120.3 |
C21—C20—C19 | 120.8 (4) | C57—C58—C59 | 120.2 (4) |
C21—C20—H20 | 119.6 | C57—C58—H58 | 119.9 |
C19—C20—H20 | 119.6 | C59—C58—H58 | 119.9 |
C22—C21—C20 | 119.9 (3) | C58—C59—C54 | 120.2 (4) |
C22—C21—H21 | 120.1 | C58—C59—H59 | 119.9 |
C20—C21—H21 | 120.1 | C54—C59—H59 | 119.9 |
C21—C22—C23 | 120.0 (4) | O4—C60—N4 | 122.8 (3) |
C21—C22—H22 | 120.0 | O4—C60—C40 | 119.3 (3) |
C23—C22—H22 | 120.0 | N4—C60—C40 | 117.7 (3) |
C22—C23—C18 | 120.6 (4) | C66—C61—C62 | 120.1 (3) |
C22—C23—H23 | 119.7 | C66—C61—N4 | 121.1 (3) |
C18—C23—H23 | 119.7 | C62—C61—N4 | 118.7 (3) |
O2—C24—N2 | 121.5 (3) | C63—C62—C61 | 119.7 (4) |
O2—C24—C4 | 120.8 (3) | C63—C62—H62 | 120.2 |
N2—C24—C4 | 117.7 (3) | C61—C62—H62 | 120.2 |
C26—C25—C30 | 121.3 (3) | C62—C63—C64 | 119.7 (4) |
C26—C25—N2 | 119.7 (3) | C62—C63—H63 | 120.2 |
C30—C25—N2 | 119.0 (3) | C64—C63—H63 | 120.2 |
C25—C26—C27 | 119.7 (4) | C65—C64—C63 | 121.1 (4) |
C25—C26—H26 | 120.2 | C65—C64—H64 | 119.5 |
C27—C26—H26 | 120.2 | C63—C64—H64 | 119.5 |
C28—C27—C26 | 119.8 (3) | C64—C65—C66 | 118.8 (4) |
C28—C27—H27 | 120.1 | C64—C65—H65 | 120.6 |
C26—C27—H27 | 120.1 | C66—C65—H65 | 120.6 |
C27—C28—C29 | 119.6 (4) | C61—C66—C65 | 120.6 (4) |
C27—C28—H28 | 120.2 | C61—C66—H66 | 119.7 |
C29—C28—H28 | 120.2 | C65—C66—H66 | 119.7 |
C30—C29—C28 | 120.8 (4) | C72—C67—C68 | 120.7 (3) |
C30—C29—H29 | 119.6 | C72—C67—N4 | 120.6 (3) |
C28—C29—H29 | 119.6 | C68—C67—N4 | 118.7 (3) |
C25—C30—C29 | 118.8 (3) | C69—C68—C67 | 119.1 (3) |
C25—C30—H30 | 120.6 | C69—C68—H68 | 120.5 |
C29—C30—H30 | 120.6 | C67—C68—H68 | 120.5 |
C32—C31—C36 | 119.7 (3) | C70—C69—C68 | 120.0 (3) |
C32—C31—N2 | 119.2 (3) | C70—C69—H69 | 120.0 |
C36—C31—N2 | 121.1 (3) | C68—C69—H69 | 120.0 |
C33—C32—C31 | 120.1 (4) | C69—C70—C71 | 120.5 (3) |
C33—C32—H32 | 119.9 | C69—C70—H70 | 119.7 |
C31—C32—H32 | 119.9 | C71—C70—H70 | 119.7 |
C34—C33—C32 | 120.4 (4) | C72—C71—C70 | 119.3 (3) |
C34—C33—H33 | 119.8 | C72—C71—H71 | 120.3 |
C32—C33—H33 | 119.8 | C70—C71—H71 | 120.3 |
C35—C34—C33 | 119.7 (3) | C67—C72—C71 | 120.4 (3) |
C35—C34—H34 | 120.2 | C67—C72—H72 | 119.8 |
C33—C34—H34 | 120.2 | C71—C72—H72 | 119.8 |
C9—C1—C2—C3 | −1.2 (4) | C45—C37—C38—C39 | −1.8 (5) |
C11—C1—C2—C3 | 175.9 (3) | C47—C37—C38—C39 | 172.8 (3) |
C1—C2—C3—C4 | 0.4 (5) | C37—C38—C39—C40 | 0.4 (5) |
C2—C3—C4—C10 | 1.1 (5) | C38—C39—C40—C46 | 1.8 (5) |
C2—C3—C4—C24 | −172.1 (3) | C38—C39—C40—C60 | −174.7 (3) |
C10—C5—C6—C7 | −1.1 (6) | C46—C41—C42—C43 | −0.4 (5) |
C5—C6—C7—C8 | 2.0 (6) | C41—C42—C43—C44 | −0.4 (5) |
C6—C7—C8—C9 | −0.9 (5) | C42—C43—C44—C45 | 0.5 (5) |
C7—C8—C9—C10 | −0.9 (5) | C38—C37—C45—C46 | 1.1 (4) |
C7—C8—C9—C1 | 177.4 (3) | C47—C37—C45—C46 | −173.4 (3) |
C2—C1—C9—C10 | 0.5 (4) | C38—C37—C45—C44 | −176.6 (3) |
C11—C1—C9—C10 | −176.7 (3) | C47—C37—C45—C44 | 8.9 (5) |
C2—C1—C9—C8 | −177.7 (3) | C43—C44—C45—C46 | 0.0 (5) |
C11—C1—C9—C8 | 5.1 (4) | C43—C44—C45—C37 | 177.7 (3) |
C8—C9—C10—C4 | 179.3 (3) | C37—C45—C46—C41 | −178.5 (3) |
C1—C9—C10—C4 | 1.0 (4) | C44—C45—C46—C41 | −0.8 (4) |
C8—C9—C10—C5 | 1.6 (4) | C37—C45—C46—C40 | 1.0 (4) |
C1—C9—C10—C5 | −176.6 (3) | C44—C45—C46—C40 | 178.8 (3) |
C3—C4—C10—C9 | −1.8 (4) | C42—C41—C46—C45 | 0.9 (5) |
C24—C4—C10—C9 | 171.2 (3) | C42—C41—C46—C40 | −178.6 (3) |
C3—C4—C10—C5 | 175.8 (3) | C39—C40—C46—C45 | −2.5 (4) |
C24—C4—C10—C5 | −11.2 (5) | C60—C40—C46—C45 | 174.2 (3) |
C6—C5—C10—C9 | −0.7 (5) | C39—C40—C46—C41 | 177.0 (3) |
C6—C5—C10—C4 | −178.3 (3) | C60—C40—C46—C41 | −6.3 (4) |
C18—N1—C11—O1 | −173.0 (3) | C54—N3—C47—O3 | −159.9 (4) |
C12—N1—C11—O1 | −8.8 (5) | C48—N3—C47—O3 | 14.4 (5) |
C18—N1—C11—C1 | 7.6 (5) | C54—N3—C47—C37 | 22.4 (5) |
C12—N1—C11—C1 | 171.8 (3) | C48—N3—C47—C37 | −163.3 (3) |
C2—C1—C11—O1 | −113.1 (4) | C38—C37—C47—O3 | −118.5 (4) |
C9—C1—C11—O1 | 64.1 (4) | C45—C37—C47—O3 | 56.1 (5) |
C2—C1—C11—N1 | 66.3 (4) | C38—C37—C47—N3 | 59.2 (4) |
C9—C1—C11—N1 | −116.6 (3) | C45—C37—C47—N3 | −126.2 (3) |
C11—N1—C12—C17 | 118.4 (3) | C47—N3—C48—C53 | −126.1 (4) |
C18—N1—C12—C17 | −76.5 (4) | C54—N3—C48—C53 | 48.5 (5) |
C11—N1—C12—C13 | −66.8 (4) | C47—N3—C48—C49 | 55.6 (5) |
C18—N1—C12—C13 | 98.3 (3) | C54—N3—C48—C49 | −129.8 (4) |
C17—C12—C13—C14 | 1.1 (5) | C53—C48—C49—C50 | −0.6 (6) |
N1—C12—C13—C14 | −173.8 (3) | N3—C48—C49—C50 | 177.7 (3) |
C12—C13—C14—C15 | 1.5 (5) | C48—C49—C50—C51 | 0.0 (6) |
C13—C14—C15—C16 | −2.3 (5) | C49—C50—C51—C52 | 0.6 (6) |
C14—C15—C16—C17 | 0.5 (5) | C50—C51—C52—C53 | −0.6 (6) |
C15—C16—C17—C12 | 2.0 (5) | C49—C48—C53—C52 | 0.6 (5) |
C13—C12—C17—C16 | −2.8 (5) | N3—C48—C53—C52 | −177.7 (3) |
N1—C12—C17—C16 | 171.9 (3) | C51—C52—C53—C48 | 0.0 (5) |
C11—N1—C18—C23 | 61.9 (5) | C47—N3—C54—C55 | −141.9 (4) |
C12—N1—C18—C23 | −102.8 (4) | C48—N3—C54—C55 | 43.7 (5) |
C11—N1—C18—C19 | −118.8 (4) | C47—N3—C54—C59 | 40.9 (5) |
C12—N1—C18—C19 | 76.4 (4) | C48—N3—C54—C59 | −133.5 (4) |
C23—C18—C19—C20 | 0.9 (5) | C59—C54—C55—C56 | 1.3 (5) |
N1—C18—C19—C20 | −178.4 (3) | N3—C54—C55—C56 | −175.9 (3) |
C18—C19—C20—C21 | −2.5 (6) | C54—C55—C56—C57 | −2.2 (6) |
C19—C20—C21—C22 | 2.5 (6) | C55—C56—C57—C58 | 1.0 (6) |
C20—C21—C22—C23 | −0.7 (6) | C56—C57—C58—C59 | 1.0 (6) |
C21—C22—C23—C18 | −1.0 (6) | C57—C58—C59—C54 | −1.9 (6) |
C19—C18—C23—C22 | 0.9 (6) | C55—C54—C59—C58 | 0.7 (5) |
N1—C18—C23—C22 | −179.9 (3) | N3—C54—C59—C58 | 177.9 (3) |
C31—N2—C24—O2 | 166.9 (3) | C67—N4—C60—O4 | −165.4 (3) |
C25—N2—C24—O2 | −13.4 (5) | C61—N4—C60—O4 | 7.8 (5) |
C31—N2—C24—C4 | −15.2 (5) | C67—N4—C60—C40 | 19.8 (5) |
C25—N2—C24—C4 | 164.6 (3) | C61—N4—C60—C40 | −167.0 (3) |
C3—C4—C24—O2 | 116.2 (4) | C39—C40—C60—O4 | 91.3 (4) |
C10—C4—C24—O2 | −56.9 (5) | C46—C40—C60—O4 | −85.3 (4) |
C3—C4—C24—N2 | −61.8 (4) | C39—C40—C60—N4 | −93.7 (4) |
C10—C4—C24—N2 | 125.1 (4) | C46—C40—C60—N4 | 89.7 (4) |
C24—N2—C25—C26 | 119.6 (4) | C60—N4—C61—C66 | −126.6 (4) |
C31—N2—C25—C26 | −60.6 (4) | C67—N4—C61—C66 | 46.6 (5) |
C24—N2—C25—C30 | −61.7 (4) | C60—N4—C61—C62 | 53.7 (5) |
C31—N2—C25—C30 | 118.0 (3) | C67—N4—C61—C62 | −133.1 (4) |
C30—C25—C26—C27 | 0.5 (5) | C66—C61—C62—C63 | 1.1 (6) |
N2—C25—C26—C27 | 179.1 (3) | N4—C61—C62—C63 | −179.2 (3) |
C25—C26—C27—C28 | 0.4 (5) | C61—C62—C63—C64 | −2.5 (6) |
C26—C27—C28—C29 | −1.0 (5) | C62—C63—C64—C65 | 2.6 (6) |
C27—C28—C29—C30 | 0.8 (5) | C63—C64—C65—C66 | −1.4 (6) |
C26—C25—C30—C29 | −0.7 (5) | C62—C61—C66—C65 | 0.1 (6) |
N2—C25—C30—C29 | −179.3 (3) | N4—C61—C66—C65 | −179.6 (3) |
C28—C29—C30—C25 | 0.1 (5) | C64—C65—C66—C61 | 0.0 (6) |
C24—N2—C31—C32 | 138.0 (4) | C60—N4—C67—C72 | −91.8 (4) |
C25—N2—C31—C32 | −41.7 (4) | C61—N4—C67—C72 | 94.9 (4) |
C24—N2—C31—C36 | −44.5 (5) | C60—N4—C67—C68 | 87.6 (4) |
C25—N2—C31—C36 | 135.8 (3) | C61—N4—C67—C68 | −85.7 (4) |
C36—C31—C32—C33 | −0.3 (5) | C72—C67—C68—C69 | −0.4 (5) |
N2—C31—C32—C33 | 177.2 (3) | N4—C67—C68—C69 | −179.9 (3) |
C31—C32—C33—C34 | 1.9 (6) | C67—C68—C69—C70 | 1.7 (5) |
C32—C33—C34—C35 | −1.5 (6) | C68—C69—C70—C71 | −1.4 (6) |
C33—C34—C35—C36 | −0.4 (6) | C69—C70—C71—C72 | −0.4 (6) |
C32—C31—C36—C35 | −1.6 (5) | C68—C67—C72—C71 | −1.3 (5) |
N2—C31—C36—C35 | −179.1 (3) | N4—C67—C72—C71 | 178.1 (3) |
C34—C35—C36—C31 | 2.0 (5) | C70—C71—C72—C67 | 1.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.95 | 2.41 | 3.342 (4) | 166 |
C30—H30···O1ii | 0.95 | 2.48 | 3.413 (4) | 168 |
C65—H65···O3iii | 0.95 | 2.59 | 3.420 (4) | 146 |
C42—H42···O4iv | 0.95 | 2.51 | 3.105 (4) | 120 |
C68—H68···O4v | 0.95 | 2.35 | 3.209 (4) | 150 |
C16—H16···Cg2vi | 0.95 | 2.85 | 3.443 (1) | 122 |
C21—H21···Cg4 | 0.95 | 2.90 | 3.643 (1) | 135 |
C39—H39···Cg4vii | 0.95 | 2.86 | 3.430 (1) | 119 |
C44—H44···Cg3vi | 0.95 | 2.90 | 3.600 (1) | 132 |
C69—H69···Cg2viii | 0.95 | 2.87 | 3.711 (4) | 148 |
C71—H71···Cg1 | 0.95 | 2.91 | 3.670 (1) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x−1, y+1, z; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+1, −z+2; (vi) x+1, y−1, z; (vii) −x+1, −y+2, −z+2; (viii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C36H26N2O2 |
Mr | 518.59 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 2624.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.49 × 0.28 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20350, 9674, 5904 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.192, 1.00 |
No. of reflections | 9674 |
No. of parameters | 722 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.40 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.95 | 2.41 | 3.342 (4) | 166 |
C30—H30···O1ii | 0.95 | 2.48 | 3.413 (4) | 168 |
C65—H65···O3iii | 0.95 | 2.59 | 3.420 (4) | 146 |
C42—H42···O4iv | 0.95 | 2.51 | 3.105 (4) | 120 |
C68—H68···O4v | 0.95 | 2.35 | 3.209 (4) | 150 |
C16—H16···Cg2vi | 0.95 | 2.85 | 3.443 (1) | 122 |
C21—H21···Cg4 | 0.95 | 2.90 | 3.643 (1) | 135 |
C39—H39···Cg4vii | 0.95 | 2.86 | 3.430 (1) | 119 |
C44—H44···Cg3vi | 0.95 | 2.90 | 3.600 (1) | 132 |
C69—H69···Cg2viii | 0.95 | 2.87 | 3.711 (4) | 148 |
C71—H71···Cg1 | 0.95 | 2.91 | 3.670 (1) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x−1, y+1, z; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+1, −z+2; (vi) x+1, y−1, z; (vii) −x+1, −y+2, −z+2; (viii) x, y−1, z. |
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)