The title compound, also known as 2-amino-5-[4-(octylamino)phenyl]tropone, C21H28N2O, contains two crystallographically independent molecules in the asymmetric unit. The NH2 group of the 2-aminotropone unit and the NH group of the aminobenzene unit participate in intermolecular hydrogen bonding with the O atoms of neighbouring molecules. An intermolecular π–π interaction is observed in the crystal structure.
Supporting information
CCDC reference: 282273
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.004 Å
- R factor = 0.071
- wR factor = 0.202
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.49
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.29
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H2 ... ?
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
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et
al., 2002); software used to prepare material for publication: CrystalStructure.
2-Amino-5-[4-(octylamino)phenyl]cyclohepta-2,4,6-trien-1-one
top
Crystal data top
C21H28N2O | Z = 4 |
Mr = 324.46 | F(000) = 704.00 |
Triclinic, P1 | Dx = 1.176 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.691 (2) Å | Cell parameters from 2903 reflections |
b = 14.882 (4) Å | θ = 3.1–27.5° |
c = 16.948 (5) Å | µ = 0.07 mm−1 |
α = 77.200 (14)° | T = 123 K |
β = 77.262 (14)° | Platelet, yellow |
γ = 80.658 (14)° | 0.12 × 0.10 × 0.03 mm |
V = 1832.0 (9) Å3 | |
Data collection top
Rigaku Saturn diffractometer | 3759 reflections with I > 2σ(I) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.064 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −9→9 |
Tmin = 0.991, Tmax = 0.998 | k = −19→19 |
22067 measured reflections | l = −21→21 |
8302 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.0015Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.071 | (Δ/σ)max < 0.001 |
wR(F2) = 0.202 | Δρmax = 0.53 e Å−3 |
S = 1.00 | Δρmin = −0.49 e Å−3 |
8285 reflections | Extinction correction: Larson (1970), eq. 22 |
508 parameters | Extinction coefficient: 156 (60) |
H atoms treated by a mixture of independent and constrained refinement | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.5904 (2) | −0.17499 (12) | 0.92294 (13) | 0.0420 (5) | |
O2 | −0.7684 (2) | 0.43864 (12) | 0.87833 (14) | 0.0497 (6) | |
N1 | −0.8196 (2) | −0.03081 (19) | 0.93900 (18) | 0.0430 (7) | |
N2 | 0.2986 (2) | 0.29675 (14) | 0.77113 (17) | 0.0412 (7) | |
N3 | −0.5656 (3) | 0.32250 (17) | 0.9663 (2) | 0.0439 (7) | |
N4 | 0.2345 (3) | 0.83994 (16) | 0.77863 (19) | 0.0435 (7) | |
C1 | −0.5203 (3) | −0.09927 (17) | 0.90830 (19) | 0.0355 (7) | |
C2 | −0.6465 (3) | −0.01504 (18) | 0.91794 (19) | 0.0356 (7) | |
C3 | −0.6016 (3) | 0.07370 (17) | 0.90716 (19) | 0.0374 (7) | |
C4 | −0.4381 (3) | 0.10978 (17) | 0.88252 (19) | 0.0369 (7) | |
C5 | −0.2648 (3) | 0.06720 (17) | 0.85957 (19) | 0.0336 (7) | |
C6 | −0.2234 (3) | −0.02941 (17) | 0.8607 (2) | 0.0371 (7) | |
C7 | −0.3326 (3) | −0.09895 (17) | 0.88204 (19) | 0.0369 (7) | |
C8 | −0.1156 (3) | 0.12548 (16) | 0.83487 (19) | 0.0342 (7) | |
C9 | −0.1198 (3) | 0.20149 (17) | 0.8727 (2) | 0.0368 (7) | |
C10 | 0.0160 (3) | 0.25720 (17) | 0.8509 (2) | 0.0375 (7) | |
C11 | 0.1656 (3) | 0.24104 (17) | 0.78853 (19) | 0.0359 (7) | |
C12 | 0.1713 (3) | 0.16649 (17) | 0.74969 (19) | 0.0372 (7) | |
C13 | 0.0338 (3) | 0.11064 (17) | 0.77316 (19) | 0.0372 (7) | |
C14 | 0.4667 (3) | 0.28704 (17) | 0.7130 (2) | 0.0414 (8) | |
C15 | 0.5838 (3) | 0.35556 (18) | 0.7225 (2) | 0.0407 (8) | |
C16 | 0.7680 (3) | 0.35629 (18) | 0.6666 (2) | 0.0420 (8) | |
C17 | 0.8603 (3) | 0.43722 (18) | 0.6725 (2) | 0.0466 (8) | |
C18 | 1.0458 (3) | 0.44315 (19) | 0.6208 (2) | 0.0456 (8) | |
C19 | 1.1335 (3) | 0.52461 (19) | 0.6299 (2) | 0.0551 (9) | |
C20 | 1.3160 (3) | 0.5337 (2) | 0.5746 (2) | 0.0580 (10) | |
C21 | 1.4047 (4) | 0.6141 (2) | 0.5834 (2) | 0.0765 (13) | |
C22 | −0.6227 (3) | 0.46744 (18) | 0.8805 (2) | 0.0412 (8) | |
C23 | −0.5026 (3) | 0.40458 (18) | 0.9309 (2) | 0.0405 (8) | |
C24 | −0.3362 (3) | 0.42076 (18) | 0.9403 (2) | 0.0398 (8) | |
C25 | −0.2389 (3) | 0.49549 (17) | 0.9095 (2) | 0.0398 (8) | |
C26 | −0.2790 (3) | 0.58025 (18) | 0.8581 (2) | 0.0405 (8) | |
C27 | −0.4383 (3) | 0.60486 (18) | 0.8269 (2) | 0.0437 (8) | |
C28 | −0.5826 (3) | 0.55685 (17) | 0.8357 (2) | 0.0414 (8) | |
C29 | −0.1476 (3) | 0.64890 (18) | 0.8373 (2) | 0.0373 (8) | |
C30 | −0.0504 (3) | 0.65994 (17) | 0.8950 (2) | 0.0385 (8) | |
C31 | 0.0725 (3) | 0.72352 (17) | 0.8753 (2) | 0.0376 (8) | |
C32 | 0.1094 (3) | 0.77758 (18) | 0.7957 (2) | 0.0387 (8) | |
C33 | 0.0146 (3) | 0.76721 (18) | 0.7378 (2) | 0.0431 (8) | |
C34 | −0.1108 (3) | 0.70448 (18) | 0.7583 (2) | 0.0411 (8) | |
C35 | 0.3114 (3) | 0.88325 (19) | 0.6964 (2) | 0.0440 (8) | |
C36 | 0.4656 (3) | 0.93323 (19) | 0.6991 (2) | 0.0449 (8) | |
C37 | 0.5510 (3) | 0.9897 (2) | 0.6175 (2) | 0.0478 (9) | |
C38 | 0.7103 (3) | 1.03365 (19) | 0.6257 (2) | 0.0465 (9) | |
C39 | 0.8001 (4) | 1.0925 (2) | 0.5465 (2) | 0.0490 (9) | |
C40 | 0.9623 (4) | 1.1326 (2) | 0.5568 (2) | 0.0480 (9) | |
C41 | 1.0564 (4) | 1.1906 (2) | 0.4788 (2) | 0.0546 (10) | |
C42 | 1.2145 (4) | 1.2326 (2) | 0.4903 (2) | 0.0646 (11) | |
H1 | −0.840 (3) | −0.088 (2) | 0.939 (2) | 0.056 (9)* | |
H2 | −0.901 (4) | 0.013 (2) | 0.937 (2) | 0.053 (9)* | |
H3 | −0.7016 | 0.1186 | 0.9191 | 0.046* | |
H4 | −0.4461 | 0.1745 | 0.8810 | 0.046* | |
H5 | −0.0997 | −0.0494 | 0.8437 | 0.046* | |
H6 | −0.2693 | −0.1587 | 0.8785 | 0.046* | |
H7 | −0.2196 | 0.2146 | 0.9146 | 0.045* | |
H8 | 0.0091 | 0.3072 | 0.8783 | 0.046* | |
H9 | 0.2699 | 0.1542 | 0.7071 | 0.044* | |
H10 | 0.0415 | 0.0601 | 0.7462 | 0.046* | |
H11 | 0.277 (3) | 0.3474 (19) | 0.7977 (17) | 0.036 (7)* | |
H12 | 0.5250 | 0.2255 | 0.7244 | 0.048* | |
H13 | 0.4445 | 0.3005 | 0.6583 | 0.048* | |
H14 | 0.5209 | 0.4161 | 0.7117 | 0.047* | |
H15 | 0.6010 | 0.3412 | 0.7779 | 0.047* | |
H16 | 0.8401 | 0.2998 | 0.6826 | 0.048* | |
H17 | 0.7546 | 0.3619 | 0.6113 | 0.048* | |
H18 | 0.7873 | 0.4931 | 0.6557 | 0.052* | |
H19 | 0.8689 | 0.4317 | 0.7285 | 0.052* | |
H20 | 1.1195 | 0.3873 | 0.6370 | 0.050* | |
H21 | 1.0381 | 0.4498 | 0.5646 | 0.051* | |
H22 | 1.0569 | 0.5802 | 0.6163 | 0.061* | |
H23 | 1.1466 | 0.5164 | 0.6855 | 0.061* | |
H24 | 1.3923 | 0.4779 | 0.5880 | 0.063* | |
H25 | 1.3027 | 0.5422 | 0.5189 | 0.063* | |
H26 | 1.3713 | 0.6680 | 0.5454 | 0.086* | |
H27 | 1.5315 | 0.5992 | 0.5725 | 0.086* | |
H28 | 1.3664 | 0.6254 | 0.6380 | 0.086* | |
H29 | −0.672 (4) | 0.320 (2) | 0.9586 (19) | 0.047 (8)* | |
H30 | −0.524 (4) | 0.279 (2) | 1.011 (2) | 0.087 (13)* | |
H31 | −0.2785 | 0.3710 | 0.9748 | 0.050* | |
H32 | −0.1259 | 0.4878 | 0.9257 | 0.050* | |
H33 | −0.4484 | 0.6652 | 0.7936 | 0.055* | |
H34 | −0.6722 | 0.5897 | 0.8060 | 0.053* | |
H35 | −0.0695 | 0.6227 | 0.9487 | 0.046* | |
H36 | 0.1326 | 0.7309 | 0.9164 | 0.046* | |
H37 | 0.0363 | 0.8034 | 0.6836 | 0.053* | |
H38 | −0.1742 | 0.6991 | 0.7177 | 0.051* | |
H39 | 0.298 (3) | 0.828 (2) | 0.825 (2) | 0.051 (9)* | |
H40 | 0.3541 | 0.8372 | 0.6635 | 0.052* | |
H41 | 0.2225 | 0.9266 | 0.6731 | 0.053* | |
H42 | 0.4223 | 0.9742 | 0.7367 | 0.053* | |
H43 | 0.5563 | 0.8880 | 0.7188 | 0.053* | |
H44 | 0.5911 | 0.9500 | 0.5786 | 0.056* | |
H45 | 0.4634 | 1.0375 | 0.5985 | 0.056* | |
H46 | 0.6693 | 1.0720 | 0.6657 | 0.055* | |
H47 | 0.7975 | 0.9853 | 0.6442 | 0.055* | |
H48 | 0.8383 | 1.0550 | 0.5058 | 0.056* | |
H49 | 0.7147 | 1.1424 | 0.5288 | 0.056* | |
H50 | 0.9231 | 1.1705 | 0.5971 | 0.055* | |
H51 | 1.0462 | 1.0824 | 0.5755 | 0.055* | |
H52 | 0.9718 | 1.2396 | 0.4591 | 0.062* | |
H53 | 1.0994 | 1.1522 | 0.4390 | 0.062* | |
H54 | 1.1737 | 1.2918 | 0.5042 | 0.075* | |
H55 | 1.3013 | 1.2390 | 0.4405 | 0.075* | |
H56 | 1.2672 | 1.1932 | 0.5333 | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0319 (9) | 0.0266 (9) | 0.0725 (16) | −0.0055 (7) | −0.0150 (9) | −0.0135 (9) |
O2 | 0.0333 (10) | 0.0327 (10) | 0.0931 (19) | 0.0005 (8) | −0.0223 (10) | −0.0261 (11) |
N1 | 0.0256 (11) | 0.0311 (13) | 0.076 (2) | 0.0023 (10) | −0.0178 (12) | −0.0148 (13) |
N2 | 0.0327 (11) | 0.0269 (11) | 0.0639 (19) | −0.0063 (9) | 0.0007 (11) | −0.0163 (12) |
N3 | 0.0339 (13) | 0.0283 (12) | 0.073 (2) | −0.0019 (10) | −0.0117 (13) | −0.0167 (13) |
N4 | 0.0460 (13) | 0.0317 (12) | 0.0553 (19) | −0.0118 (11) | −0.0113 (13) | −0.0070 (12) |
C1 | 0.0307 (13) | 0.0249 (12) | 0.055 (2) | −0.0034 (10) | −0.0140 (12) | −0.0116 (12) |
C2 | 0.0257 (12) | 0.0306 (13) | 0.056 (2) | 0.0007 (10) | −0.0171 (12) | −0.0125 (13) |
C3 | 0.0291 (13) | 0.0269 (12) | 0.059 (2) | 0.0048 (10) | −0.0142 (13) | −0.0141 (13) |
C4 | 0.0335 (13) | 0.0227 (12) | 0.058 (2) | 0.0016 (10) | −0.0152 (13) | −0.0136 (12) |
C5 | 0.0308 (12) | 0.0233 (12) | 0.0514 (19) | −0.0025 (10) | −0.0145 (12) | −0.0110 (12) |
C6 | 0.0294 (12) | 0.0248 (12) | 0.060 (2) | 0.0019 (10) | −0.0110 (13) | −0.0151 (13) |
C7 | 0.0295 (12) | 0.0223 (12) | 0.062 (2) | 0.0036 (10) | −0.0150 (13) | −0.0139 (13) |
C8 | 0.0293 (12) | 0.0215 (11) | 0.053 (2) | 0.0004 (10) | −0.0101 (12) | −0.0103 (12) |
C9 | 0.0305 (13) | 0.0249 (12) | 0.057 (2) | 0.0007 (10) | −0.0090 (13) | −0.0141 (12) |
C10 | 0.0314 (13) | 0.0216 (12) | 0.062 (2) | 0.0015 (10) | −0.0107 (13) | −0.0149 (12) |
C11 | 0.0301 (13) | 0.0222 (12) | 0.054 (2) | −0.0008 (10) | −0.0061 (12) | −0.0070 (12) |
C12 | 0.0327 (13) | 0.0247 (12) | 0.053 (2) | −0.0009 (11) | −0.0040 (13) | −0.0108 (12) |
C13 | 0.0362 (14) | 0.0244 (12) | 0.054 (2) | 0.0022 (11) | −0.0123 (13) | −0.0143 (13) |
C14 | 0.0338 (13) | 0.0230 (12) | 0.062 (2) | −0.0020 (11) | −0.0015 (13) | −0.0064 (13) |
C15 | 0.0372 (14) | 0.0248 (12) | 0.057 (2) | −0.0046 (11) | −0.0018 (13) | −0.0072 (13) |
C16 | 0.0357 (14) | 0.0268 (13) | 0.057 (2) | −0.0014 (11) | −0.0020 (13) | −0.0037 (13) |
C17 | 0.0361 (14) | 0.0277 (13) | 0.066 (2) | −0.0032 (11) | 0.0048 (14) | −0.0038 (14) |
C18 | 0.0345 (14) | 0.0315 (14) | 0.060 (2) | −0.0020 (12) | 0.0025 (14) | 0.0003 (14) |
C19 | 0.0378 (15) | 0.0283 (14) | 0.086 (2) | −0.0039 (12) | 0.0080 (16) | −0.0038 (15) |
C20 | 0.0431 (16) | 0.0382 (16) | 0.076 (2) | −0.0059 (14) | 0.0052 (16) | 0.0085 (16) |
C21 | 0.0492 (19) | 0.0473 (19) | 0.117 (3) | −0.0138 (16) | 0.007 (2) | 0.000 (2) |
C22 | 0.0295 (13) | 0.0277 (13) | 0.072 (2) | 0.0054 (11) | −0.0144 (14) | −0.0240 (14) |
C23 | 0.0343 (13) | 0.0243 (12) | 0.067 (2) | 0.0027 (11) | −0.0107 (14) | −0.0212 (13) |
C24 | 0.0316 (13) | 0.0249 (13) | 0.068 (2) | 0.0038 (11) | −0.0176 (13) | −0.0158 (13) |
C25 | 0.0278 (12) | 0.0265 (13) | 0.070 (2) | 0.0039 (10) | −0.0152 (13) | −0.0195 (13) |
C26 | 0.0322 (13) | 0.0257 (12) | 0.070 (2) | 0.0017 (11) | −0.0138 (13) | −0.0214 (13) |
C27 | 0.0384 (14) | 0.0259 (13) | 0.073 (2) | 0.0053 (11) | −0.0200 (15) | −0.0193 (14) |
C28 | 0.0357 (14) | 0.0251 (13) | 0.070 (2) | 0.0052 (11) | −0.0221 (14) | −0.0180 (14) |
C29 | 0.0308 (13) | 0.0261 (13) | 0.059 (2) | 0.0041 (11) | −0.0136 (13) | −0.0164 (13) |
C30 | 0.0274 (12) | 0.0261 (13) | 0.062 (2) | 0.0042 (10) | −0.0109 (13) | −0.0117 (13) |
C31 | 0.0286 (12) | 0.0275 (13) | 0.060 (2) | 0.0010 (10) | −0.0153 (13) | −0.0121 (13) |
C32 | 0.0346 (13) | 0.0238 (12) | 0.061 (2) | 0.0008 (11) | −0.0126 (13) | −0.0140 (13) |
C33 | 0.0446 (15) | 0.0287 (13) | 0.058 (2) | −0.0024 (12) | −0.0117 (15) | −0.0122 (14) |
C34 | 0.0393 (14) | 0.0296 (13) | 0.060 (2) | 0.0007 (11) | −0.0180 (14) | −0.0147 (14) |
C35 | 0.0452 (15) | 0.0315 (14) | 0.055 (2) | −0.0016 (12) | −0.0086 (15) | −0.0101 (14) |
C36 | 0.0445 (16) | 0.0283 (13) | 0.060 (2) | −0.0028 (12) | −0.0052 (15) | −0.0091 (14) |
C37 | 0.0492 (17) | 0.0346 (15) | 0.056 (2) | −0.0041 (13) | −0.0043 (15) | −0.0085 (14) |
C38 | 0.0510 (17) | 0.0306 (14) | 0.055 (2) | −0.0066 (13) | −0.0018 (15) | −0.0086 (14) |
C39 | 0.0536 (18) | 0.0359 (15) | 0.051 (2) | −0.0044 (14) | −0.0007 (15) | −0.0045 (14) |
C40 | 0.0541 (17) | 0.0315 (14) | 0.053 (2) | −0.0082 (13) | 0.0034 (15) | −0.0074 (14) |
C41 | 0.0597 (19) | 0.0410 (17) | 0.055 (2) | −0.0035 (15) | −0.0020 (17) | −0.0040 (15) |
C42 | 0.064 (2) | 0.0512 (19) | 0.071 (2) | −0.0105 (17) | 0.0027 (19) | −0.0083 (19) |
Geometric parameters (Å, º) top
O1—C1 | 1.279 (3) | N3—H29 | 0.87 (3) |
O2—C22 | 1.274 (3) | N3—H30 | 0.97 (3) |
N1—C2 | 1.345 (3) | N4—H39 | 0.98 (3) |
N2—C11 | 1.362 (3) | C3—H3 | 0.950 |
N2—C14 | 1.451 (3) | C4—H4 | 0.950 |
N3—C23 | 1.352 (3) | C6—H5 | 0.950 |
N4—C32 | 1.385 (3) | C7—H6 | 0.950 |
N4—C35 | 1.439 (4) | C9—H7 | 0.950 |
C1—C2 | 1.472 (3) | C10—H8 | 0.950 |
C1—C7 | 1.414 (3) | C12—H9 | 0.950 |
C2—C3 | 1.382 (3) | C13—H10 | 0.950 |
C3—C4 | 1.390 (3) | C14—H12 | 0.950 |
C4—C5 | 1.391 (3) | C14—H13 | 0.950 |
C5—C6 | 1.418 (3) | C15—H14 | 0.950 |
C5—C8 | 1.482 (3) | C15—H15 | 0.950 |
C6—C7 | 1.375 (3) | C16—H16 | 0.950 |
C8—C9 | 1.411 (4) | C16—H17 | 0.950 |
C8—C13 | 1.397 (3) | C17—H18 | 0.950 |
C9—C10 | 1.374 (3) | C17—H19 | 0.950 |
C10—C11 | 1.409 (3) | C18—H20 | 0.950 |
C11—C12 | 1.400 (4) | C18—H21 | 0.950 |
C12—C13 | 1.386 (3) | C19—H22 | 0.950 |
C14—C15 | 1.521 (4) | C19—H23 | 0.950 |
C15—C16 | 1.521 (3) | C20—H24 | 0.950 |
C16—C17 | 1.525 (4) | C20—H25 | 0.950 |
C17—C18 | 1.506 (3) | C21—H26 | 0.950 |
C18—C19 | 1.530 (4) | C21—H27 | 0.950 |
C19—C20 | 1.513 (4) | C21—H28 | 0.950 |
C20—C21 | 1.519 (5) | C24—H31 | 0.950 |
C22—C23 | 1.473 (4) | C25—H32 | 0.950 |
C22—C28 | 1.423 (3) | C27—H33 | 0.950 |
C23—C24 | 1.389 (4) | C28—H34 | 0.950 |
C24—C25 | 1.382 (3) | C30—H35 | 0.950 |
C25—C26 | 1.397 (3) | C31—H36 | 0.950 |
C26—C27 | 1.404 (4) | C33—H37 | 0.950 |
C26—C29 | 1.486 (3) | C34—H38 | 0.950 |
C27—C28 | 1.379 (4) | C35—H40 | 0.950 |
C29—C30 | 1.405 (4) | C35—H41 | 0.950 |
C29—C34 | 1.405 (4) | C36—H42 | 0.950 |
C30—C31 | 1.382 (3) | C36—H43 | 0.950 |
C31—C32 | 1.406 (4) | C37—H44 | 0.950 |
C32—C33 | 1.392 (5) | C37—H45 | 0.950 |
C33—C34 | 1.387 (4) | C38—H46 | 0.950 |
C35—C36 | 1.512 (4) | C38—H47 | 0.950 |
C36—C37 | 1.521 (4) | C39—H48 | 0.950 |
C37—C38 | 1.524 (4) | C39—H49 | 0.950 |
C38—C39 | 1.521 (4) | C40—H50 | 0.950 |
C39—C40 | 1.525 (4) | C40—H51 | 0.950 |
C40—C41 | 1.514 (4) | C41—H52 | 0.950 |
C41—C42 | 1.520 (5) | C41—H53 | 0.950 |
N1—H1 | 0.89 (3) | C42—H54 | 0.950 |
N1—H2 | 0.83 (3) | C42—H55 | 0.950 |
N2—H11 | 0.93 (3) | C42—H56 | 0.950 |
| | | |
O1···N3i | 2.845 (3) | C10···H19iii | 3.166 |
O1···N4ii | 2.993 (4) | C10···H31 | 3.262 |
O1···C31ii | 3.520 (3) | C11···H3v | 2.805 |
O2···N2iii | 2.993 (3) | C11···H4v | 3.574 |
O2···C10iii | 3.550 (3) | C11···H16iii | 3.291 |
O2···C25iii | 3.529 (3) | C11···H19iii | 3.455 |
N1···N1iv | 3.210 (3) | C11···H20iii | 3.022 |
N1···N4ii | 3.580 (4) | C12···H2v | 3.46 (3) |
N1···C5i | 3.523 (4) | C12···H3v | 3.132 |
N1···C8iii | 3.455 (3) | C12···H16iii | 3.218 |
N1···C13iii | 3.407 (3) | C12···H20iii | 3.425 |
N2···O2v | 2.993 (3) | C12···H42ix | 3.204 |
N2···C4v | 3.597 (3) | C12···H50ii | 3.522 |
N3···O1i | 2.845 (3) | C12···H56ii | 3.523 |
N3···C1i | 3.573 (3) | C13···H2v | 2.94 (3) |
N3···C26vi | 3.486 (4) | C13···H3v | 3.564 |
N3···C30vi | 3.358 (3) | C13···H16iii | 3.198 |
N4···O1vii | 2.993 (4) | C13···H41ix | 3.488 |
N4···N1vii | 3.580 (4) | C13···H42ix | 3.348 |
N4···C1vii | 3.531 (4) | C13···H50ii | 3.180 |
C1···N3i | 3.573 (3) | C13···H51ii | 3.446 |
C1···N4ii | 3.531 (4) | C14···H4v | 3.119 |
C1···C3i | 3.570 (4) | C14···H20iii | 3.223 |
C1···C4i | 3.459 (4) | C14···H24iii | 3.197 |
C1···C36ii | 3.495 (4) | C14···H46ix | 3.504 |
C2···C4i | 3.522 (4) | C15···H4v | 3.354 |
C3···C1i | 3.570 (4) | C15···H24iii | 3.074 |
C3···C7i | 3.591 (4) | C16···H24iii | 3.512 |
C3···C11iii | 3.372 (3) | C16···H25xii | 3.294 |
C3···C12iii | 3.423 (4) | C16···H50ix | 3.194 |
C4···N2iii | 3.597 (3) | C18···H13v | 3.531 |
C4···C1i | 3.459 (4) | C18···H21xii | 3.342 |
C4···C2i | 3.522 (4) | C18···H54ix | 3.215 |
C4···C14iii | 3.563 (3) | C19···H14v | 3.561 |
C5···N1i | 3.523 (4) | C19···H38v | 3.567 |
C7···C3i | 3.591 (4) | C19···H52xiii | 3.537 |
C8···N1v | 3.455 (3) | C20···H13v | 3.516 |
C10···O2v | 3.550 (3) | C20···H14v | 3.142 |
C11···C3v | 3.372 (3) | C20···H17xii | 3.308 |
C12···C3v | 3.423 (4) | C20···H24viii | 3.166 |
C13···N1v | 3.407 (3) | C20···H25viii | 3.172 |
C14···C4v | 3.563 (3) | C20···H27viii | 3.413 |
C15···C22v | 3.422 (4) | C21···H14v | 3.372 |
C20···C20viii | 3.530 (4) | C21···H18v | 3.506 |
C22···C15iii | 3.422 (4) | C21···H24viii | 3.439 |
C23···C25vi | 3.454 (4) | C21···H25viii | 3.442 |
C25···O2v | 3.529 (3) | C21···H52xiii | 3.439 |
C25···C23vi | 3.454 (4) | C21···H55xiv | 3.297 |
C26···N3vi | 3.486 (4) | C22···H11iii | 2.79 (3) |
C28···C31iii | 3.385 (3) | C22···H14iii | 3.047 |
C30···N3vi | 3.358 (3) | C22···H15iii | 2.931 |
C31···O1vii | 3.520 (3) | C22···H32vi | 3.567 |
C31···C28v | 3.385 (3) | C22···H35vi | 3.475 |
C36···C1vii | 3.495 (4) | C22···H35vi | 3.475 |
O1···H4i | 3.398 | C23···H7 | 3.301 |
O1···H7i | 2.803 | C23···H11iii | 3.42 (3) |
O1···H29i | 3.35 (3) | C23···H15iii | 2.859 |
O1···H30i | 1.90 (3) | C23···H35vi | 3.503 |
O1···H31i | 3.236 | C24···H7 | 3.153 |
O1···H33ix | 3.473 | C24···H8 | 3.018 |
O1···H36ii | 2.766 | C24···H15iii | 3.380 |
O1···H39ii | 2.02 (3) | C24···H19iii | 3.568 |
O1···H42ii | 3.425 | C24···H36xv | 3.397 |
O1···H43ii | 3.363 | C25···H8 | 3.200 |
O2···H8iii | 2.800 | C25···H19iii | 3.304 |
O2···H11iii | 2.07 (3) | C26···H19iii | 3.352 |
O2···H14iii | 3.232 | C26···H30vi | 3.34 (4) |
O2···H15iii | 3.270 | C27···H30vi | 3.50 (4) |
O2···H23x | 3.386 | C27···H39iii | 3.59 (2) |
O2···H32iii | 2.716 | C28···H14iii | 3.179 |
O2···H35iii | 3.530 | C28···H15iii | 3.544 |
O2···H35vi | 2.925 | C28···H28x | 3.370 |
N1···H1iv | 3.46 (3) | C28···H31vi | 3.500 |
N1···H2iv | 2.68 (2) | C28···H36iii | 3.433 |
N1···H5iii | 3.041 | C29···H6xi | 3.048 |
N1···H7i | 3.284 | C29···H29vi | 3.53 (3) |
N1···H10iii | 3.572 | C29···H30vi | 3.41 (3) |
N1···H39ii | 3.07 (3) | C29···H34v | 3.568 |
N1···H42ii | 3.513 | C30···H6xi | 2.931 |
N2···H3v | 3.221 | C30···H29vi | 2.93 (2) |
N2···H4v | 3.095 | C30···H30vi | 3.39 (3) |
N2···H20iii | 2.882 | C30···H34v | 3.099 |
N2···H23iii | 3.400 | C31···H1vii | 3.42 (3) |
N2···H29v | 3.33 (3) | C31···H5xi | 3.394 |
N3···H4 | 2.821 | C31···H6xi | 2.910 |
N3···H6i | 3.340 | C31···H31xv | 3.226 |
N3···H7 | 2.940 | C31···H34v | 2.821 |
N3···H11iii | 3.27 (3) | C32···H1vii | 3.58 (3) |
N3···H15iii | 3.136 | C32···H5xi | 2.981 |
N3···H35vi | 2.934 | C32···H6xi | 3.040 |
N4···H1vii | 3.04 (3) | C32···H33v | 3.535 |
N4···H5xi | 2.952 | C32···H34v | 3.010 |
N4···H10xi | 3.350 | C33···H5xi | 3.485 |
N4···H33v | 3.271 | C33···H6xi | 3.124 |
C1···H4i | 3.463 | C33···H28iii | 3.513 |
C1···H7i | 3.485 | C33···H34v | 3.453 |
C1···H30i | 2.72 (3) | C33···H52xvi | 3.338 |
C1···H39ii | 2.68 (3) | C33···H53xvi | 3.226 |
C1···H42ii | 2.974 | C34···H6xi | 3.117 |
C1···H43ii | 3.178 | C34···H22iii | 3.272 |
C2···H39ii | 3.22 (3) | C34···H23iii | 3.454 |
C2···H42ii | 3.035 | C34···H43iii | 3.484 |
C3···H12iii | 3.455 | C34···H52xvi | 3.550 |
C3···H42ii | 3.485 | C34···H53xvi | 3.537 |
C4···H12iii | 2.892 | C35···H10xi | 3.223 |
C4···H15iii | 3.534 | C36···H9xi | 3.405 |
C4···H30 | 3.57 (4) | C36···H10xi | 3.516 |
C5···H2v | 3.26 (3) | C37···H9xi | 3.384 |
C5···H12iii | 3.380 | C37···H53xiii | 3.244 |
C5···H46ii | 3.418 | C38···H12xi | 3.567 |
C6···H1v | 3.40 (3) | C38···H53xiii | 3.211 |
C6···H2v | 3.24 (3) | C39···H48xiii | 3.337 |
C6···H46ii | 3.532 | C39···H51xiii | 3.572 |
C6···H47ii | 3.596 | C39···H53xiii | 3.562 |
C7···H3i | 3.383 | C40···H10vii | 3.310 |
C7···H30i | 3.09 (3) | C40···H16xi | 3.511 |
C7···H39ii | 3.59 (3) | C40···H48xiii | 3.236 |
C7···H42ii | 3.316 | C41···H22xiii | 3.494 |
C7···H43ii | 3.124 | C41···H37xvi | 2.972 |
C8···H2v | 2.76 (3) | C41···H38xvi | 3.368 |
C8···H16iii | 3.261 | C41···H44xiii | 3.251 |
C9···H1i | 3.24 (3) | C41···H47xiii | 3.590 |
C9···H2v | 3.13 (3) | C41···H48xiii | 3.576 |
C9···H3v | 3.447 | C42···H22xiii | 3.595 |
C9···H15iii | 3.179 | C42···H27xiv | 3.271 |
C9···H16iii | 3.289 | C42···H38xvi | 3.514 |
C9···H31 | 3.294 | C42···H44xiii | 3.208 |
C10···H3v | 2.984 | C42···H45v | 3.583 |
C10···H16iii | 3.316 | | |
| | | |
C11—N2—C14 | 126.2 (2) | C14—C15—H14 | 107.9 |
C32—N4—C35 | 123.4 (3) | C14—C15—H15 | 107.7 |
O1—C1—C2 | 116.0 (2) | C16—C15—H14 | 107.8 |
O1—C1—C7 | 120.4 (2) | C16—C15—H15 | 107.7 |
C2—C1—C7 | 123.6 (2) | H14—C15—H15 | 109.5 |
N1—C2—C1 | 113.5 (2) | C15—C16—H16 | 109.1 |
N1—C2—C3 | 120.3 (2) | C15—C16—H17 | 109.0 |
C1—C2—C3 | 126.2 (2) | C17—C16—H16 | 109.0 |
C2—C3—C4 | 132.3 (2) | C17—C16—H17 | 109.2 |
C3—C4—C5 | 130.9 (2) | H16—C16—H17 | 109.5 |
C4—C5—C6 | 123.3 (2) | C16—C17—H18 | 107.9 |
C4—C5—C8 | 118.2 (2) | C16—C17—H19 | 108.1 |
C6—C5—C8 | 118.4 (2) | C18—C17—H18 | 108.0 |
C5—C6—C7 | 130.7 (2) | C18—C17—H19 | 108.0 |
C1—C7—C6 | 132.8 (2) | H18—C17—H19 | 109.5 |
C5—C8—C9 | 120.6 (2) | C17—C18—H20 | 108.5 |
C5—C8—C13 | 123.2 (2) | C17—C18—H21 | 108.6 |
C9—C8—C13 | 116.2 (2) | C19—C18—H20 | 108.4 |
C8—C9—C10 | 122.1 (2) | C19—C18—H21 | 108.6 |
C9—C10—C11 | 120.9 (2) | H20—C18—H21 | 109.5 |
N2—C11—C10 | 118.4 (2) | C18—C19—H22 | 108.4 |
N2—C11—C12 | 123.7 (2) | C18—C19—H23 | 108.6 |
C10—C11—C12 | 117.9 (2) | C20—C19—H22 | 108.3 |
C11—C12—C13 | 120.3 (2) | C20—C19—H23 | 108.6 |
C8—C13—C12 | 122.7 (2) | H22—C19—H23 | 109.5 |
N2—C14—C15 | 107.8 (2) | C19—C20—H24 | 108.2 |
C14—C15—C16 | 116.1 (2) | C19—C20—H25 | 108.6 |
C15—C16—C17 | 111.0 (2) | C21—C20—H24 | 108.2 |
C16—C17—C18 | 115.3 (2) | C21—C20—H25 | 108.5 |
C17—C18—C19 | 113.3 (2) | H24—C20—H25 | 109.5 |
C18—C19—C20 | 113.4 (2) | C20—C21—H26 | 109.3 |
C19—C20—C21 | 113.8 (3) | C20—C21—H27 | 109.7 |
O2—C22—C23 | 117.0 (2) | C20—C21—H28 | 109.4 |
O2—C22—C28 | 120.0 (2) | H26—C21—H27 | 109.5 |
C23—C22—C28 | 123.0 (2) | H26—C21—H28 | 109.5 |
N3—C23—C22 | 112.9 (2) | H27—C21—H28 | 109.5 |
N3—C23—C24 | 120.4 (2) | C23—C24—H31 | 113.8 |
C22—C23—C24 | 126.7 (2) | C25—C24—H31 | 113.9 |
C23—C24—C25 | 132.3 (2) | C24—C25—H32 | 114.7 |
C24—C25—C26 | 130.6 (2) | C26—C25—H32 | 114.7 |
C25—C26—C27 | 123.6 (2) | C26—C27—H33 | 114.3 |
C25—C26—C29 | 118.0 (2) | C28—C27—H33 | 114.3 |
C27—C26—C29 | 118.4 (2) | C22—C28—H34 | 113.8 |
C26—C27—C28 | 131.4 (2) | C27—C28—H34 | 113.8 |
C22—C28—C27 | 132.4 (2) | C29—C30—H35 | 119.1 |
C26—C29—C30 | 121.7 (2) | C31—C30—H35 | 119.2 |
C26—C29—C34 | 121.7 (3) | C30—C31—H36 | 119.5 |
C30—C29—C34 | 116.6 (2) | C32—C31—H36 | 119.5 |
C29—C30—C31 | 121.6 (2) | C32—C33—H37 | 119.7 |
C30—C31—C32 | 121.0 (3) | C34—C33—H37 | 119.7 |
N4—C32—C31 | 119.0 (3) | C29—C34—H38 | 118.9 |
N4—C32—C33 | 123.0 (2) | C33—C34—H38 | 119.0 |
C31—C32—C33 | 118.0 (2) | N4—C35—H40 | 109.5 |
C32—C33—C34 | 120.7 (2) | N4—C35—H41 | 109.4 |
C29—C34—C33 | 122.1 (3) | C36—C35—H40 | 109.5 |
N4—C35—C36 | 109.6 (2) | C36—C35—H41 | 109.4 |
C35—C36—C37 | 116.0 (3) | H40—C35—H41 | 109.5 |
C36—C37—C38 | 112.1 (2) | C35—C36—H42 | 107.8 |
C37—C38—C39 | 114.8 (3) | C35—C36—H43 | 107.8 |
C38—C39—C40 | 113.0 (2) | C37—C36—H42 | 107.9 |
C39—C40—C41 | 114.4 (3) | C37—C36—H43 | 107.8 |
C40—C41—C42 | 114.1 (3) | H42—C36—H43 | 109.5 |
C2—N1—H1 | 115.8 (18) | C36—C37—H44 | 108.8 |
C2—N1—H2 | 120 (2) | C36—C37—H45 | 108.8 |
H1—N1—H2 | 121 (3) | C38—C37—H44 | 108.8 |
C11—N2—H11 | 116.4 (15) | C38—C37—H45 | 108.8 |
C14—N2—H11 | 117.4 (15) | H44—C37—H45 | 109.5 |
C23—N3—H29 | 113.2 (18) | C37—C38—H46 | 108.1 |
C23—N3—H30 | 125 (2) | C37—C38—H47 | 108.1 |
H29—N3—H30 | 118 (2) | C39—C38—H46 | 108.1 |
C32—N4—H39 | 108.6 (17) | C39—C38—H47 | 108.1 |
C35—N4—H39 | 122.6 (16) | H46—C38—H47 | 109.5 |
C2—C3—H3 | 113.8 | C38—C39—H48 | 108.6 |
C4—C3—H3 | 113.9 | C38—C39—H49 | 108.6 |
C3—C4—H4 | 114.5 | C40—C39—H48 | 108.6 |
C5—C4—H4 | 114.6 | C40—C39—H49 | 108.6 |
C5—C6—H5 | 114.7 | H48—C39—H49 | 109.5 |
C7—C6—H5 | 114.6 | C39—C40—H50 | 108.2 |
C1—C7—H6 | 113.6 | C39—C40—H51 | 108.2 |
C6—C7—H6 | 113.6 | C41—C40—H50 | 108.2 |
C8—C9—H7 | 119.0 | C41—C40—H51 | 108.3 |
C10—C9—H7 | 118.9 | H50—C40—H51 | 109.5 |
C9—C10—H8 | 119.6 | C40—C41—H52 | 108.4 |
C11—C10—H8 | 119.5 | C40—C41—H53 | 108.3 |
C11—C12—H9 | 119.8 | C42—C41—H52 | 108.4 |
C13—C12—H9 | 119.9 | C42—C41—H53 | 108.2 |
C8—C13—H10 | 118.7 | H52—C41—H53 | 109.5 |
C12—C13—H10 | 118.6 | C41—C42—H54 | 109.4 |
N2—C14—H12 | 109.9 | C41—C42—H55 | 109.6 |
N2—C14—H13 | 109.9 | C41—C42—H56 | 109.5 |
C15—C14—H12 | 110.0 | H54—C42—H55 | 109.5 |
C15—C14—H13 | 109.8 | H54—C42—H56 | 109.5 |
H12—C14—H13 | 109.5 | H55—C42—H56 | 109.5 |
| | | |
C11—N2—C14—C15 | −172.2 (2) | C16—C17—C18—C19 | −179.2 (2) |
C14—N2—C11—C10 | 175.9 (2) | C17—C18—C19—C20 | −177.0 (2) |
C14—N2—C11—C12 | −2.0 (4) | C18—C19—C20—C21 | −179.7 (2) |
C32—N4—C35—C36 | −169.9 (2) | O2—C22—C23—N3 | 1.7 (4) |
C35—N4—C32—C31 | 165.8 (2) | O2—C22—C23—C24 | 178.3 (3) |
C35—N4—C32—C33 | −15.7 (3) | O2—C22—C28—C27 | −179.9 (2) |
O1—C1—C2—N1 | −1.6 (4) | C23—C22—C28—C27 | 0.3 (5) |
O1—C1—C2—C3 | 178.6 (3) | C28—C22—C23—N3 | −178.5 (3) |
O1—C1—C7—C6 | 178.4 (3) | C28—C22—C23—C24 | −1.9 (5) |
C2—C1—C7—C6 | 0.5 (5) | N3—C23—C24—C25 | 177.8 (3) |
C7—C1—C2—N1 | 176.4 (3) | C22—C23—C24—C25 | 1.4 (6) |
C7—C1—C2—C3 | −3.4 (5) | C23—C24—C25—C26 | 0.2 (5) |
N1—C2—C3—C4 | −176.8 (3) | C24—C25—C26—C27 | −0.1 (4) |
C1—C2—C3—C4 | 2.9 (6) | C24—C25—C26—C29 | 178.2 (3) |
C2—C3—C4—C5 | 0.9 (6) | C25—C26—C27—C28 | −1.4 (5) |
C3—C4—C5—C6 | −2.6 (5) | C25—C26—C29—C30 | −36.6 (4) |
C3—C4—C5—C8 | 179.1 (3) | C25—C26—C29—C34 | 141.8 (2) |
C4—C5—C6—C7 | 0.4 (5) | C27—C26—C29—C30 | 141.8 (2) |
C4—C5—C8—C9 | 34.2 (4) | C27—C26—C29—C34 | −39.8 (4) |
C4—C5—C8—C13 | −144.6 (2) | C29—C26—C27—C28 | −179.8 (3) |
C6—C5—C8—C9 | −144.2 (3) | C26—C27—C28—C22 | 1.7 (6) |
C6—C5—C8—C13 | 37.0 (4) | C26—C29—C30—C31 | 179.7 (2) |
C8—C5—C6—C7 | 178.7 (3) | C26—C29—C34—C33 | −178.5 (2) |
C5—C6—C7—C1 | 1.4 (6) | C30—C29—C34—C33 | −0.0 (3) |
C5—C8—C9—C10 | −179.6 (2) | C34—C29—C30—C31 | 1.2 (3) |
C5—C8—C13—C12 | 179.0 (2) | C29—C30—C31—C32 | −2.2 (3) |
C9—C8—C13—C12 | 0.1 (3) | C30—C31—C32—N4 | −179.5 (2) |
C13—C8—C9—C10 | −0.7 (4) | C30—C31—C32—C33 | 1.9 (3) |
C8—C9—C10—C11 | 0.8 (4) | N4—C32—C33—C34 | −179.2 (2) |
C9—C10—C11—N2 | −178.1 (2) | C31—C32—C33—C34 | −0.7 (3) |
C9—C10—C11—C12 | −0.1 (3) | C32—C33—C34—C29 | −0.2 (4) |
N2—C11—C12—C13 | 177.4 (2) | N4—C35—C36—C37 | −174.9 (2) |
C10—C11—C12—C13 | −0.5 (4) | C35—C36—C37—C38 | −177.3 (2) |
C11—C12—C13—C8 | 0.5 (4) | C36—C37—C38—C39 | −179.0 (2) |
N2—C14—C15—C16 | 179.9 (2) | C37—C38—C39—C40 | −178.1 (2) |
C14—C15—C16—C17 | 171.3 (2) | C38—C39—C40—C41 | 179.2 (2) |
C15—C16—C17—C18 | 178.8 (2) | C39—C40—C41—C42 | 178.3 (2) |
Symmetry codes: (i) −x−1, −y, −z+2; (ii) x−1, y−1, z; (iii) x−1, y, z; (iv) −x−2, −y, −z+2; (v) x+1, y, z; (vi) −x−1, −y+1, −z+2; (vii) x+1, y+1, z; (viii) −x+3, −y+1, −z+1; (ix) x, y−1, z; (x) x−2, y, z; (xi) x, y+1, z; (xii) −x+2, −y+1, −z+1; (xiii) −x+2, −y+2, −z+1; (xiv) −x+3, −y+2, −z+1; (xv) −x, −y+1, −z+2; (xvi) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.89 (3) | 2.13 (2) | 2.570 (2) | 109 (2) |
N2—H11···O2v | 0.93 (3) | 2.07 (3) | 2.993 (3) | 168 (2) |
N3—H29···O2 | 0.87 (3) | 2.11 (2) | 2.579 (3) | 113 (2) |
N3—H30···O1i | 0.97 (3) | 1.90 (3) | 2.845 (3) | 165 (3) |
N4—H39···O1vii | 0.98 (3) | 2.02 (3) | 2.993 (4) | 170 (2) |
Symmetry codes: (i) −x−1, −y, −z+2; (v) x+1, y, z; (vii) x+1, y+1, z. |