Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020682/na6115sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020682/na6115Isup2.hkl |
CCDC reference: 180545
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.006 Å
- R factor = 0.060
- wR factor = 0.146
- Data-to-parameter ratio = 8.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.45 From the CIF: _reflns_number_total 3086 Count of symmetry unique reflns 3138 Completeness (_total/calc) 98.34% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
A mixture of 2-methyl-2,3-dihydro-1H-indoline (8.4 mmol), benzotriazole (8.4 mmol) and formaldehyde (37% w/w solution, 12.6 mmol) in 10 ml of ethyl ether, was stirred at room temperature for 30 min. and the resulting precipitate was filtered and recrystallized from ethanol. White crystals (suitable for X-ray diffraction), 86% yield; m.p. 343 K. Analysis calculated for C16H16N4 (264.12): C, 72.70; H, 6.10; N, 21.20%; found: C, 72.73; H, 6.08; N, 21.17%.
H atoms were treated as riding atoms with C—H = 0.90–0.98 Å, N—H = 0.90 Å and O—H = 0.82 Å. The absolute configuration was not determined. Friedel pairs were merged.
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C16H16N4 | Dx = 1.319 Mg m−3 |
Mr = 264.33 | Melting point: 343K K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5660 (3) Å | Cell parameters from 3086 reflections |
b = 17.7842 (8) Å | θ = 3.0–27.5° |
c = 10.2284 (4) Å | µ = 0.08 mm−1 |
β = 104.689 (3)° | T = 120 K |
V = 1331.30 (10) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.10 × 0.03 mm |
F(000) = 560 |
Kappa-CCD diffractometer | 3086 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.988, Tmax = 0.998 | k = −20→23 |
10746 measured reflections | l = −11→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3 |
3086 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.37 e Å−3 |
C16H16N4 | V = 1331.30 (10) Å3 |
Mr = 264.33 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.5660 (3) Å | µ = 0.08 mm−1 |
b = 17.7842 (8) Å | T = 120 K |
c = 10.2284 (4) Å | 0.15 × 0.10 × 0.03 mm |
β = 104.689 (3)° |
Kappa-CCD diffractometer | 3086 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 2083 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.998 | Rint = 0.074 |
10746 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 1 restraint |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.32 e Å−3 |
3086 reflections | Δρmin = −0.37 e Å−3 |
363 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8200 (5) | 0.40980 (19) | 0.0108 (3) | 0.0241 (8) | |
N2 | 0.7833 (5) | 0.4746 (2) | 0.0732 (3) | 0.0296 (8) | |
N3 | 0.6998 (5) | 0.5216 (2) | −0.0177 (4) | 0.0304 (9) | |
C3A | 0.6820 (6) | 0.4893 (2) | −0.1430 (4) | 0.0266 (10) | |
C4 | 0.6019 (6) | 0.5174 (3) | −0.2746 (4) | 0.0312 (10) | |
C5 | 0.6103 (6) | 0.4736 (3) | −0.3808 (4) | 0.0302 (10) | |
C6 | 0.6900 (6) | 0.4007 (3) | −0.3617 (4) | 0.0315 (10) | |
C7 | 0.7655 (5) | 0.3720 (3) | −0.2356 (4) | 0.0264 (9) | |
C7A | 0.7580 (5) | 0.4175 (2) | −0.1262 (4) | 0.0246 (9) | |
C11 | 0.9185 (5) | 0.3476 (2) | 0.0945 (4) | 0.0237 (9) | |
N11 | 0.8098 (5) | 0.28369 (19) | 0.1098 (3) | 0.0231 (8) | |
C12 | 0.7561 (6) | 0.2268 (2) | −0.0007 (4) | 0.0249 (10) | |
C121 | 0.9153 (6) | 0.1854 (3) | −0.0286 (5) | 0.0315 (11) | |
C13 | 0.6222 (6) | 0.1763 (2) | 0.0528 (4) | 0.0268 (10) | |
C13A | 0.5441 (6) | 0.2303 (2) | 0.1367 (4) | 0.0239 (9) | |
C14 | 0.3894 (6) | 0.2250 (2) | 0.1846 (4) | 0.0258 (9) | |
C15 | 0.3530 (6) | 0.2829 (2) | 0.2661 (4) | 0.0261 (10) | |
C16 | 0.4702 (5) | 0.3442 (2) | 0.2985 (4) | 0.0244 (9) | |
C17 | 0.6269 (5) | 0.3496 (3) | 0.2504 (4) | 0.0226 (9) | |
C17A | 0.6615 (5) | 0.2919 (2) | 0.1692 (4) | 0.0217 (9) | |
N21 | 0.9170 (4) | −0.04286 (19) | 0.4760 (3) | 0.0226 (8) | |
N22 | 0.8702 (5) | −0.10494 (19) | 0.5390 (3) | 0.0283 (9) | |
N23 | 0.7856 (5) | −0.1531 (2) | 0.4460 (3) | 0.0296 (8) | |
C23A | 0.7793 (6) | −0.1225 (2) | 0.3213 (4) | 0.0260 (10) | |
C24 | 0.7049 (6) | −0.1514 (3) | 0.1918 (4) | 0.0306 (10) | |
C25 | 0.7165 (6) | −0.1081 (3) | 0.0831 (4) | 0.0315 (11) | |
C26 | 0.8042 (6) | −0.0367 (3) | 0.1032 (4) | 0.0285 (10) | |
C27 | 0.8779 (6) | −0.0076 (2) | 0.2283 (4) | 0.0259 (9) | |
C27A | 0.8624 (5) | −0.0515 (2) | 0.3382 (4) | 0.0219 (9) | |
C21 | 1.0189 (5) | 0.0179 (2) | 0.5600 (4) | 0.0233 (9) | |
N31 | 0.9171 (5) | 0.08521 (19) | 0.5664 (3) | 0.0230 (8) | |
C32 | 0.8749 (6) | 0.1392 (3) | 0.4541 (4) | 0.0303 (10) | |
C321 | 1.0373 (6) | 0.1710 (3) | 0.4146 (5) | 0.0320 (11) | |
C33 | 0.7579 (6) | 0.1978 (2) | 0.5043 (4) | 0.0277 (10) | |
C33A | 0.6648 (6) | 0.1512 (2) | 0.5903 (4) | 0.0243 (9) | |
C34 | 0.5104 (6) | 0.1634 (3) | 0.6343 (4) | 0.0309 (10) | |
C35 | 0.4578 (6) | 0.1099 (3) | 0.7158 (4) | 0.0323 (11) | |
C36 | 0.5607 (6) | 0.0457 (3) | 0.7542 (4) | 0.0295 (11) | |
C37 | 0.7183 (6) | 0.0318 (2) | 0.7101 (4) | 0.0263 (10) | |
C37A | 0.7666 (6) | 0.0847 (2) | 0.6258 (4) | 0.0237 (10) | |
H4 | 0.5446 | 0.5654 | −0.2876 | 0.037* | |
H5 | 0.5618 | 0.4918 | −0.4700 | 0.036* | |
H6 | 0.6910 | 0.3711 | −0.4387 | 0.038* | |
H7 | 0.8201 | 0.3236 | −0.2233 | 0.032* | |
H11A | 1.0175 | 0.3304 | 0.0543 | 0.028* | |
H11B | 0.9768 | 0.3677 | 0.1855 | 0.028* | |
H12 | 0.6873 | 0.2525 | −0.0853 | 0.030* | |
H12A | 0.9966 | 0.2211 | −0.0573 | 0.047* | |
H12B | 0.8709 | 0.1484 | −0.1004 | 0.047* | |
H12C | 0.9825 | 0.1595 | 0.0536 | 0.047* | |
H13A | 0.5254 | 0.1555 | −0.0225 | 0.032* | |
H13B | 0.6875 | 0.1344 | 0.1084 | 0.032* | |
H14 | 0.3098 | 0.1830 | 0.1626 | 0.031* | |
H15 | 0.2471 | 0.2804 | 0.2999 | 0.031* | |
H16 | 0.4433 | 0.3831 | 0.3542 | 0.029* | |
H17 | 0.7071 | 0.3915 | 0.2725 | 0.027* | |
H24 | 0.6482 | −0.1994 | 0.1794 | 0.037* | |
H25 | 0.6657 | −0.1260 | −0.0060 | 0.038* | |
H26 | 0.8116 | −0.0082 | 0.0262 | 0.034* | |
H27 | 0.9368 | 0.0400 | 0.2402 | 0.031* | |
H21A | 1.0667 | −0.0014 | 0.6530 | 0.028* | |
H21B | 1.1253 | 0.0311 | 0.5248 | 0.028* | |
H32 | 0.7957 | 0.1134 | 0.3734 | 0.036* | |
H32A | 1.1096 | 0.2015 | 0.4889 | 0.048* | |
H32B | 0.9959 | 0.2025 | 0.3340 | 0.048* | |
H32C | 1.1127 | 0.1298 | 0.3949 | 0.048* | |
H33A | 0.8349 | 0.2375 | 0.5583 | 0.033* | |
H33B | 0.6678 | 0.2214 | 0.4280 | 0.033* | |
H34 | 0.4404 | 0.2079 | 0.6093 | 0.037* | |
H35 | 0.3499 | 0.1176 | 0.7455 | 0.039* | |
H36 | 0.5238 | 0.0102 | 0.8116 | 0.035* | |
H37 | 0.7895 | −0.0122 | 0.7369 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0293 (19) | 0.0195 (19) | 0.0244 (17) | −0.0006 (16) | 0.0086 (15) | 0.0003 (15) |
N2 | 0.037 (2) | 0.018 (2) | 0.0342 (19) | −0.0003 (17) | 0.0117 (17) | −0.0030 (16) |
N3 | 0.034 (2) | 0.0215 (19) | 0.0358 (19) | 0.0033 (17) | 0.0098 (17) | 0.0030 (17) |
C3A | 0.028 (2) | 0.021 (2) | 0.032 (2) | −0.004 (2) | 0.0093 (19) | −0.0007 (19) |
C4 | 0.027 (2) | 0.027 (2) | 0.038 (2) | 0.000 (2) | 0.006 (2) | 0.007 (2) |
C5 | 0.025 (2) | 0.035 (3) | 0.029 (2) | −0.001 (2) | 0.0044 (18) | 0.007 (2) |
C6 | 0.033 (3) | 0.032 (3) | 0.030 (2) | 0.000 (2) | 0.0078 (19) | −0.001 (2) |
C7 | 0.027 (2) | 0.022 (2) | 0.030 (2) | 0.0006 (19) | 0.0089 (18) | −0.0002 (19) |
C7A | 0.025 (2) | 0.019 (2) | 0.030 (2) | −0.0011 (18) | 0.0086 (18) | 0.0027 (19) |
C11 | 0.025 (2) | 0.019 (2) | 0.026 (2) | −0.0013 (19) | 0.0051 (17) | 0.0003 (18) |
N11 | 0.031 (2) | 0.0168 (18) | 0.0226 (17) | −0.0044 (16) | 0.0081 (15) | 0.0001 (14) |
C12 | 0.032 (2) | 0.018 (2) | 0.024 (2) | −0.0028 (19) | 0.0071 (19) | −0.0012 (17) |
C121 | 0.026 (3) | 0.027 (3) | 0.041 (3) | 0.003 (2) | 0.008 (2) | −0.007 (2) |
C13 | 0.032 (3) | 0.018 (2) | 0.031 (2) | −0.0037 (19) | 0.0073 (19) | −0.0052 (17) |
C13A | 0.024 (2) | 0.018 (2) | 0.027 (2) | −0.0014 (18) | 0.0017 (17) | −0.0013 (18) |
C14 | 0.026 (2) | 0.019 (2) | 0.031 (2) | −0.0062 (19) | 0.0049 (18) | 0.0051 (18) |
C15 | 0.022 (2) | 0.026 (2) | 0.031 (2) | 0.0000 (19) | 0.0068 (18) | 0.0074 (19) |
C16 | 0.028 (2) | 0.020 (2) | 0.026 (2) | 0.008 (2) | 0.0076 (17) | 0.0047 (17) |
C17 | 0.025 (2) | 0.017 (2) | 0.023 (2) | −0.0019 (19) | 0.0017 (17) | 0.0022 (17) |
C17A | 0.021 (2) | 0.020 (2) | 0.0211 (19) | 0.0019 (19) | 0.0000 (16) | 0.0049 (17) |
N21 | 0.0282 (19) | 0.0139 (18) | 0.0260 (17) | 0.0031 (15) | 0.0077 (15) | 0.0008 (14) |
N22 | 0.039 (2) | 0.0160 (19) | 0.0315 (19) | 0.0008 (17) | 0.0119 (17) | 0.0037 (16) |
N23 | 0.036 (2) | 0.0187 (18) | 0.036 (2) | −0.0008 (18) | 0.0125 (16) | −0.0008 (17) |
C23A | 0.025 (2) | 0.021 (2) | 0.034 (2) | −0.0003 (19) | 0.0113 (18) | −0.0035 (19) |
C24 | 0.027 (2) | 0.024 (2) | 0.043 (3) | −0.003 (2) | 0.0117 (19) | −0.010 (2) |
C25 | 0.029 (3) | 0.034 (3) | 0.030 (2) | 0.005 (2) | 0.0047 (19) | −0.006 (2) |
C26 | 0.027 (2) | 0.032 (3) | 0.026 (2) | 0.002 (2) | 0.0066 (18) | 0.000 (2) |
C27 | 0.027 (2) | 0.018 (2) | 0.033 (2) | 0.0042 (19) | 0.0080 (19) | 0.0001 (18) |
C27A | 0.024 (2) | 0.017 (2) | 0.026 (2) | 0.0017 (18) | 0.0095 (18) | −0.0027 (17) |
C21 | 0.022 (2) | 0.020 (2) | 0.027 (2) | 0.0009 (19) | 0.0063 (18) | −0.0019 (18) |
N31 | 0.027 (2) | 0.0151 (18) | 0.0285 (18) | 0.0031 (15) | 0.0107 (16) | 0.0019 (14) |
C32 | 0.035 (3) | 0.022 (2) | 0.032 (2) | 0.005 (2) | 0.005 (2) | 0.0054 (19) |
C321 | 0.032 (3) | 0.024 (2) | 0.040 (2) | −0.004 (2) | 0.008 (2) | 0.0054 (19) |
C33 | 0.033 (3) | 0.017 (2) | 0.032 (2) | 0.0057 (19) | 0.0062 (19) | 0.0029 (18) |
C33A | 0.022 (2) | 0.025 (2) | 0.0216 (19) | 0.0027 (19) | −0.0015 (17) | −0.0040 (18) |
C34 | 0.033 (3) | 0.026 (2) | 0.029 (2) | 0.008 (2) | −0.001 (2) | −0.0040 (19) |
C35 | 0.030 (3) | 0.040 (3) | 0.027 (2) | −0.003 (2) | 0.009 (2) | −0.012 (2) |
C36 | 0.034 (3) | 0.027 (3) | 0.030 (2) | −0.006 (2) | 0.011 (2) | −0.008 (2) |
C37 | 0.039 (3) | 0.014 (2) | 0.025 (2) | −0.0002 (19) | 0.0071 (19) | −0.0031 (17) |
C37A | 0.031 (2) | 0.021 (2) | 0.0180 (19) | −0.0012 (19) | 0.0036 (18) | −0.0018 (18) |
N1—C7A | 1.367 (5) | N21—N22 | 1.369 (5) |
N1—N2 | 1.380 (5) | N21—C27A | 1.373 (5) |
N1—C11 | 1.479 (5) | N21—C21 | 1.471 (5) |
N2—N3 | 1.290 (5) | N22—N23 | 1.318 (5) |
N3—C3A | 1.380 (5) | N23—C23A | 1.376 (5) |
C3A—C7A | 1.393 (6) | C23A—C24 | 1.400 (6) |
C3A—C4 | 1.420 (6) | C23A—C27A | 1.400 (6) |
C4—C5 | 1.352 (6) | C24—C25 | 1.372 (6) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.421 (6) | C25—C26 | 1.424 (7) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—C7 | 1.370 (6) | C26—C27 | 1.361 (6) |
C6—H6 | 0.9500 | C26—H26 | 0.9500 |
C7—C7A | 1.393 (6) | C27—C27A | 1.399 (6) |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C11—N11 | 1.435 (5) | C21—N31 | 1.434 (5) |
C11—H11A | 0.9900 | C21—H21A | 0.9900 |
C11—H11B | 0.9900 | C21—H21B | 0.9900 |
N11—C17A | 1.413 (5) | N31—C37A | 1.420 (5) |
N11—C12 | 1.494 (5) | N31—C32 | 1.469 (5) |
C12—C121 | 1.500 (6) | C32—C321 | 1.499 (6) |
C12—C13 | 1.553 (6) | C32—C33 | 1.537 (6) |
C12—H12 | 1.0000 | C32—H32 | 1.0000 |
C121—H12A | 0.9800 | C321—H32A | 0.9800 |
C121—H12B | 0.9800 | C321—H32B | 0.9800 |
C121—H12C | 0.9800 | C321—H32C | 0.9800 |
C13—C13A | 1.505 (6) | C33—C33A | 1.506 (6) |
C13—H13A | 0.9900 | C33—H33A | 0.9900 |
C13—H13B | 0.9900 | C33—H33B | 0.9900 |
C13A—C14 | 1.382 (6) | C33A—C34 | 1.372 (6) |
C13A—C17A | 1.396 (6) | C33A—C37A | 1.408 (6) |
C14—C15 | 1.395 (6) | C34—C35 | 1.388 (6) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.392 (6) | C35—C36 | 1.383 (7) |
C15—H15 | 0.9500 | C35—H35 | 0.9500 |
C16—C17 | 1.398 (5) | C36—C37 | 1.400 (6) |
C16—H16 | 0.9500 | C36—H36 | 0.9500 |
C17—C17A | 1.387 (6) | C37—C37A | 1.386 (6) |
C17—H17 | 0.9500 | C37—H37 | 0.9500 |
C7A—N1—N2 | 109.5 (3) | N22—N21—C27A | 110.2 (3) |
C7A—N1—C11 | 131.3 (3) | N22—N21—C21 | 118.5 (3) |
N2—N1—C11 | 119.2 (3) | C27A—N21—C21 | 131.2 (3) |
N3—N2—N1 | 109.1 (3) | N23—N22—N21 | 108.7 (3) |
N2—N3—C3A | 108.3 (3) | N22—N23—C23A | 107.9 (3) |
N3—C3A—C7A | 109.1 (4) | N23—C23A—C24 | 130.0 (4) |
N3—C3A—C4 | 130.7 (4) | N23—C23A—C27A | 109.4 (4) |
C7A—C3A—C4 | 120.2 (4) | C24—C23A—C27A | 120.5 (4) |
C5—C4—C3A | 117.6 (4) | C25—C24—C23A | 117.9 (4) |
C5—C4—H4 | 121.2 | C25—C24—H24 | 121.0 |
C3A—C4—H4 | 121.2 | C23A—C24—H24 | 121.0 |
C4—C5—C6 | 121.4 (4) | C24—C25—C26 | 120.4 (4) |
C4—C5—H5 | 119.3 | C24—C25—H25 | 119.8 |
C6—C5—H5 | 119.3 | C26—C25—H25 | 119.8 |
C7—C6—C5 | 122.0 (4) | C27—C26—C25 | 122.7 (4) |
C7—C6—H6 | 119.0 | C27—C26—H26 | 118.7 |
C5—C6—H6 | 119.0 | C25—C26—H26 | 118.7 |
C6—C7—C7A | 116.6 (4) | C26—C27—C27A | 116.4 (4) |
C6—C7—H7 | 121.7 | C26—C27—H27 | 121.8 |
C7A—C7—H7 | 121.7 | C27A—C27—H27 | 121.8 |
N1—C7A—C7 | 133.7 (4) | N21—C27A—C27 | 134.3 (4) |
N1—C7A—C3A | 104.0 (4) | N21—C27A—C23A | 103.7 (3) |
C7—C7A—C3A | 122.2 (4) | C27—C27A—C23A | 122.0 (4) |
N11—C11—N1 | 115.9 (3) | N31—C21—N21 | 115.6 (3) |
N11—C11—H11A | 108.3 | N31—C21—H21A | 108.4 |
N1—C11—H11A | 108.3 | N21—C21—H21A | 108.4 |
N11—C11—H11B | 108.3 | N31—C21—H21B | 108.4 |
N1—C11—H11B | 108.3 | N21—C21—H21B | 108.4 |
H11A—C11—H11B | 107.4 | H21A—C21—H21B | 107.4 |
C17A—N11—C11 | 120.3 (3) | C37A—N31—C21 | 120.8 (3) |
C17A—N11—C12 | 107.6 (3) | C37A—N31—C32 | 107.4 (3) |
C11—N11—C12 | 120.5 (3) | C21—N31—C32 | 121.5 (3) |
N11—C12—C121 | 113.5 (3) | N31—C32—C321 | 115.3 (4) |
N11—C12—C13 | 101.6 (3) | N31—C32—C33 | 102.2 (3) |
C121—C12—C13 | 114.2 (4) | C321—C32—C33 | 114.5 (4) |
N11—C12—H12 | 109.1 | N31—C32—H32 | 108.1 |
C121—C12—H12 | 109.1 | C321—C32—H32 | 108.1 |
C13—C12—H12 | 109.1 | C33—C32—H32 | 108.1 |
C12—C121—H12A | 109.5 | C32—C321—H32A | 109.5 |
C12—C121—H12B | 109.5 | C32—C321—H32B | 109.5 |
H12A—C121—H12B | 109.5 | H32A—C321—H32B | 109.5 |
C12—C121—H12C | 109.5 | C32—C321—H32C | 109.5 |
H12A—C121—H12C | 109.5 | H32A—C321—H32C | 109.5 |
H12B—C121—H12C | 109.5 | H32B—C321—H32C | 109.5 |
C13A—C13—C12 | 102.5 (3) | C33A—C33—C32 | 102.5 (3) |
C13A—C13—H13A | 111.3 | C33A—C33—H33A | 111.3 |
C12—C13—H13A | 111.3 | C32—C33—H33A | 111.3 |
C13A—C13—H13B | 111.3 | C33A—C33—H33B | 111.3 |
C12—C13—H13B | 111.3 | C32—C33—H33B | 111.3 |
H13A—C13—H13B | 109.2 | H33A—C33—H33B | 109.2 |
C14—C13A—C17A | 120.9 (4) | C34—C33A—C37A | 120.2 (4) |
C14—C13A—C13 | 130.5 (4) | C34—C33A—C33 | 131.9 (4) |
C17A—C13A—C13 | 108.6 (4) | C37A—C33A—C33 | 107.9 (3) |
C13A—C14—C15 | 118.4 (4) | C33A—C34—C35 | 119.1 (4) |
C13A—C14—H14 | 120.8 | C33A—C34—H34 | 120.4 |
C15—C14—H14 | 120.8 | C35—C34—H34 | 120.4 |
C16—C15—C14 | 120.6 (4) | C36—C35—C34 | 120.7 (4) |
C16—C15—H15 | 119.7 | C36—C35—H35 | 119.6 |
C14—C15—H15 | 119.7 | C34—C35—H35 | 119.6 |
C15—C16—C17 | 121.1 (4) | C35—C36—C37 | 121.2 (4) |
C15—C16—H16 | 119.4 | C35—C36—H36 | 119.4 |
C17—C16—H16 | 119.4 | C37—C36—H36 | 119.4 |
C17A—C17—C16 | 117.7 (4) | C37A—C37—C36 | 117.5 (4) |
C17A—C17—H17 | 121.1 | C37A—C37—H37 | 121.3 |
C16—C17—H17 | 121.1 | C36—C37—H37 | 121.3 |
C17—C17A—C13A | 121.2 (4) | C37—C37A—C33A | 121.2 (4) |
C17—C17A—N11 | 128.7 (4) | C37—C37A—N31 | 129.5 (4) |
C13A—C17A—N11 | 110.1 (4) | C33A—C37A—N31 | 109.2 (3) |
C7A—N1—N2—N3 | 0.8 (4) | C27A—N21—N22—N23 | −0.6 (4) |
C11—N1—N2—N3 | 179.0 (3) | C21—N21—N22—N23 | −178.0 (3) |
N1—N2—N3—C3A | −1.0 (4) | N21—N22—N23—C23A | 0.8 (4) |
N2—N3—C3A—C7A | 0.8 (4) | N22—N23—C23A—C24 | 179.8 (4) |
N2—N3—C3A—C4 | −179.7 (4) | N22—N23—C23A—C27A | −0.7 (4) |
N3—C3A—C4—C5 | 177.6 (4) | N23—C23A—C24—C25 | 179.5 (4) |
C7A—C3A—C4—C5 | −2.9 (6) | C27A—C23A—C24—C25 | 0.1 (6) |
C3A—C4—C5—C6 | 2.3 (6) | C23A—C24—C25—C26 | 0.9 (6) |
C4—C5—C6—C7 | −1.4 (7) | C24—C25—C26—C27 | −0.7 (7) |
C5—C6—C7—C7A | 0.9 (6) | C25—C26—C27—C27A | −0.4 (6) |
N2—N1—C7A—C7 | 176.9 (4) | N22—N21—C27A—C27 | −178.5 (4) |
C11—N1—C7A—C7 | −1.0 (8) | C21—N21—C27A—C27 | −1.5 (7) |
N2—N1—C7A—C3A | −0.3 (4) | N22—N21—C27A—C23A | 0.1 (4) |
C11—N1—C7A—C3A | −178.2 (4) | C21—N21—C27A—C23A | 177.2 (4) |
C6—C7—C7A—N1 | −178.3 (4) | C26—C27—C27A—N21 | 179.8 (4) |
C6—C7—C7A—C3A | −1.5 (6) | C26—C27—C27A—C23A | 1.4 (6) |
N3—C3A—C7A—N1 | −0.3 (4) | N23—C23A—C27A—N21 | 0.3 (4) |
C4—C3A—C7A—N1 | −179.8 (4) | C24—C23A—C27A—N21 | 179.9 (4) |
N3—C3A—C7A—C7 | −177.9 (4) | N23—C23A—C27A—C27 | 179.2 (4) |
C4—C3A—C7A—C7 | 2.6 (6) | C24—C23A—C27A—C27 | −1.3 (6) |
C7A—N1—C11—N11 | −76.8 (5) | N22—N21—C21—N31 | −107.6 (4) |
N2—N1—C11—N11 | 105.6 (4) | C27A—N21—C21—N31 | 75.6 (5) |
N1—C11—N11—C17A | −60.1 (5) | N21—C21—N31—C37A | 64.4 (5) |
N1—C11—N11—C12 | 78.5 (5) | N21—C21—N31—C32 | −76.5 (5) |
C17A—N11—C12—C121 | −152.6 (3) | C37A—N31—C32—C321 | 156.6 (4) |
C11—N11—C12—C121 | 64.2 (5) | C21—N31—C32—C321 | −58.1 (5) |
C17A—N11—C12—C13 | −29.5 (4) | C37A—N31—C32—C33 | 31.6 (4) |
C11—N11—C12—C13 | −172.7 (3) | C21—N31—C32—C33 | 177.0 (4) |
N11—C12—C13—C13A | 29.0 (4) | N31—C32—C33—C33A | −30.7 (4) |
C121—C12—C13—C13A | 151.6 (4) | C321—C32—C33—C33A | −156.1 (4) |
C12—C13—C13A—C14 | 162.9 (4) | C32—C33—C33A—C34 | −160.0 (5) |
C12—C13—C13A—C17A | −19.7 (5) | C32—C33—C33A—C37A | 20.0 (4) |
C17A—C13A—C14—C15 | 0.1 (6) | C37A—C33A—C34—C35 | 1.0 (6) |
C13—C13A—C14—C15 | 177.3 (4) | C33—C33A—C34—C35 | −179.0 (4) |
C13A—C14—C15—C16 | −0.2 (6) | C33A—C34—C35—C36 | 1.0 (6) |
C14—C15—C16—C17 | 0.1 (6) | C34—C35—C36—C37 | −1.3 (6) |
C15—C16—C17—C17A | 0.1 (6) | C35—C36—C37—C37A | −0.4 (6) |
C16—C17—C17A—C13A | −0.1 (6) | C36—C37—C37A—C33A | 2.5 (6) |
C16—C17—C17A—N11 | −179.3 (4) | C36—C37—C37A—N31 | −179.9 (4) |
C14—C13A—C17A—C17 | 0.0 (6) | C34—C33A—C37A—C37 | −2.8 (6) |
C13—C13A—C17A—C17 | −177.7 (3) | C33—C33A—C37A—C37 | 177.2 (4) |
C14—C13A—C17A—N11 | 179.3 (3) | C34—C33A—C37A—N31 | 179.1 (4) |
C13—C13A—C17A—N11 | 1.6 (5) | C33—C33A—C37A—N31 | −0.9 (5) |
C11—N11—C17A—C17 | −19.0 (6) | C21—N31—C37A—C37 | 16.4 (6) |
C12—N11—C17A—C17 | −162.3 (4) | C32—N31—C37A—C37 | 162.1 (4) |
C11—N11—C17A—C13A | 161.8 (4) | C21—N31—C37A—C33A | −165.7 (4) |
C12—N11—C17A—C13A | 18.4 (4) | C32—N31—C37A—C33A | −20.1 (4) |
Experimental details
Crystal data | |
Chemical formula | C16H16N4 |
Mr | 264.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 120 |
a, b, c (Å) | 7.5660 (3), 17.7842 (8), 10.2284 (4) |
β (°) | 104.689 (3) |
V (Å3) | 1331.30 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.15 × 0.10 × 0.03 |
Data collection | |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.988, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10746, 3086, 2083 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.146, 0.98 |
No. of reflections | 3086 |
No. of parameters | 363 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.37 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2001), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
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The title compound, (I), was prepared as a precursor in the synthesis of new pyrrolo–quinoline derivatives, target compounds with potential biological and pharmacological activity (Abonia et al., 2001).
There are two molecules in the asymmetric unit and these are of opposite hand, nevertheless, a search for possible additional symmetry using the ADDSYM routine of PLATON (Spek, 2001) indicated that no additional symmetry was present. In addition repeated attempts to solve the structure in the possible centrosymmetric spacegroups were consistently unsuccesful.
There are no short inter or intramolecular contacts in the structure.
Examination of the structure with PLATON (Spek, 2001) showed that there were no solvent-accessible voids in the crystal lattice.