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There are no short inter- or intramolecular contacts in the structure of the title compound, C16H16N4, which contains two mol­ecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020682/na6115sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020682/na6115Isup2.hkl
Contains datablock I

CCDC reference: 180545

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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.

Comment top

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.

Experimental top

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%.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
1-(2-Methyl-2,3-dihydro-indol-1-ylmethyl)-1H-benzotriazole top
Crystal data top
C16H16N4Dx = 1.319 Mg m3
Mr = 264.33Melting point: 343K K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.5660 (3) ÅCell parameters from 3086 reflections
b = 17.7842 (8) Åθ = 3.0–27.5°
c = 10.2284 (4) ŵ = 0.08 mm1
β = 104.689 (3)°T = 120 K
V = 1331.30 (10) Å3Block, colourless
Z = 40.15 × 0.10 × 0.03 mm
F(000) = 560
Data collection top
Kappa-CCD
diffractometer
3086 independent reflections
Radiation source: fine-focus sealed X-ray tube2083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 99
Tmin = 0.988, Tmax = 0.998k = 2023
10746 measured reflectionsl = 1113
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-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 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = 0.37 e Å3
Crystal data top
C16H16N4V = 1331.30 (10) Å3
Mr = 264.33Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.5660 (3) ŵ = 0.08 mm1
b = 17.7842 (8) ÅT = 120 K
c = 10.2284 (4) Å0.15 × 0.10 × 0.03 mm
β = 104.689 (3)°
Data collection top
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 = 0.998Rint = 0.074
10746 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.146H-atom parameters constrained
S = 0.98Δρmax = 0.32 e Å3
3086 reflectionsΔρmin = 0.37 e Å3
363 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.8200 (5)0.40980 (19)0.0108 (3)0.0241 (8)
N20.7833 (5)0.4746 (2)0.0732 (3)0.0296 (8)
N30.6998 (5)0.5216 (2)0.0177 (4)0.0304 (9)
C3A0.6820 (6)0.4893 (2)0.1430 (4)0.0266 (10)
C40.6019 (6)0.5174 (3)0.2746 (4)0.0312 (10)
C50.6103 (6)0.4736 (3)0.3808 (4)0.0302 (10)
C60.6900 (6)0.4007 (3)0.3617 (4)0.0315 (10)
C70.7655 (5)0.3720 (3)0.2356 (4)0.0264 (9)
C7A0.7580 (5)0.4175 (2)0.1262 (4)0.0246 (9)
C110.9185 (5)0.3476 (2)0.0945 (4)0.0237 (9)
N110.8098 (5)0.28369 (19)0.1098 (3)0.0231 (8)
C120.7561 (6)0.2268 (2)0.0007 (4)0.0249 (10)
C1210.9153 (6)0.1854 (3)0.0286 (5)0.0315 (11)
C130.6222 (6)0.1763 (2)0.0528 (4)0.0268 (10)
C13A0.5441 (6)0.2303 (2)0.1367 (4)0.0239 (9)
C140.3894 (6)0.2250 (2)0.1846 (4)0.0258 (9)
C150.3530 (6)0.2829 (2)0.2661 (4)0.0261 (10)
C160.4702 (5)0.3442 (2)0.2985 (4)0.0244 (9)
C170.6269 (5)0.3496 (3)0.2504 (4)0.0226 (9)
C17A0.6615 (5)0.2919 (2)0.1692 (4)0.0217 (9)
N210.9170 (4)0.04286 (19)0.4760 (3)0.0226 (8)
N220.8702 (5)0.10494 (19)0.5390 (3)0.0283 (9)
N230.7856 (5)0.1531 (2)0.4460 (3)0.0296 (8)
C23A0.7793 (6)0.1225 (2)0.3213 (4)0.0260 (10)
C240.7049 (6)0.1514 (3)0.1918 (4)0.0306 (10)
C250.7165 (6)0.1081 (3)0.0831 (4)0.0315 (11)
C260.8042 (6)0.0367 (3)0.1032 (4)0.0285 (10)
C270.8779 (6)0.0076 (2)0.2283 (4)0.0259 (9)
C27A0.8624 (5)0.0515 (2)0.3382 (4)0.0219 (9)
C211.0189 (5)0.0179 (2)0.5600 (4)0.0233 (9)
N310.9171 (5)0.08521 (19)0.5664 (3)0.0230 (8)
C320.8749 (6)0.1392 (3)0.4541 (4)0.0303 (10)
C3211.0373 (6)0.1710 (3)0.4146 (5)0.0320 (11)
C330.7579 (6)0.1978 (2)0.5043 (4)0.0277 (10)
C33A0.6648 (6)0.1512 (2)0.5903 (4)0.0243 (9)
C340.5104 (6)0.1634 (3)0.6343 (4)0.0309 (10)
C350.4578 (6)0.1099 (3)0.7158 (4)0.0323 (11)
C360.5607 (6)0.0457 (3)0.7542 (4)0.0295 (11)
C370.7183 (6)0.0318 (2)0.7101 (4)0.0263 (10)
C37A0.7666 (6)0.0847 (2)0.6258 (4)0.0237 (10)
H40.54460.56540.28760.037*
H50.56180.49180.47000.036*
H60.69100.37110.43870.038*
H70.82010.32360.22330.032*
H11A1.01750.33040.05430.028*
H11B0.97680.36770.18550.028*
H120.68730.25250.08530.030*
H12A0.99660.22110.05730.047*
H12B0.87090.14840.10040.047*
H12C0.98250.15950.05360.047*
H13A0.52540.15550.02250.032*
H13B0.68750.13440.10840.032*
H140.30980.18300.16260.031*
H150.24710.28040.29990.031*
H160.44330.38310.35420.029*
H170.70710.39150.27250.027*
H240.64820.19940.17940.037*
H250.66570.12600.00600.038*
H260.81160.00820.02620.034*
H270.93680.04000.24020.031*
H21A1.06670.00140.65300.028*
H21B1.12530.03110.52480.028*
H320.79570.11340.37340.036*
H32A1.10960.20150.48890.048*
H32B0.99590.20250.33400.048*
H32C1.11270.12980.39490.048*
H33A0.83490.23750.55830.033*
H33B0.66780.22140.42800.033*
H340.44040.20790.60930.037*
H350.34990.11760.74550.039*
H360.52380.01020.81160.035*
H370.78950.01220.73690.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0293 (19)0.0195 (19)0.0244 (17)0.0006 (16)0.0086 (15)0.0003 (15)
N20.037 (2)0.018 (2)0.0342 (19)0.0003 (17)0.0117 (17)0.0030 (16)
N30.034 (2)0.0215 (19)0.0358 (19)0.0033 (17)0.0098 (17)0.0030 (17)
C3A0.028 (2)0.021 (2)0.032 (2)0.004 (2)0.0093 (19)0.0007 (19)
C40.027 (2)0.027 (2)0.038 (2)0.000 (2)0.006 (2)0.007 (2)
C50.025 (2)0.035 (3)0.029 (2)0.001 (2)0.0044 (18)0.007 (2)
C60.033 (3)0.032 (3)0.030 (2)0.000 (2)0.0078 (19)0.001 (2)
C70.027 (2)0.022 (2)0.030 (2)0.0006 (19)0.0089 (18)0.0002 (19)
C7A0.025 (2)0.019 (2)0.030 (2)0.0011 (18)0.0086 (18)0.0027 (19)
C110.025 (2)0.019 (2)0.026 (2)0.0013 (19)0.0051 (17)0.0003 (18)
N110.031 (2)0.0168 (18)0.0226 (17)0.0044 (16)0.0081 (15)0.0001 (14)
C120.032 (2)0.018 (2)0.024 (2)0.0028 (19)0.0071 (19)0.0012 (17)
C1210.026 (3)0.027 (3)0.041 (3)0.003 (2)0.008 (2)0.007 (2)
C130.032 (3)0.018 (2)0.031 (2)0.0037 (19)0.0073 (19)0.0052 (17)
C13A0.024 (2)0.018 (2)0.027 (2)0.0014 (18)0.0017 (17)0.0013 (18)
C140.026 (2)0.019 (2)0.031 (2)0.0062 (19)0.0049 (18)0.0051 (18)
C150.022 (2)0.026 (2)0.031 (2)0.0000 (19)0.0068 (18)0.0074 (19)
C160.028 (2)0.020 (2)0.026 (2)0.008 (2)0.0076 (17)0.0047 (17)
C170.025 (2)0.017 (2)0.023 (2)0.0019 (19)0.0017 (17)0.0022 (17)
C17A0.021 (2)0.020 (2)0.0211 (19)0.0019 (19)0.0000 (16)0.0049 (17)
N210.0282 (19)0.0139 (18)0.0260 (17)0.0031 (15)0.0077 (15)0.0008 (14)
N220.039 (2)0.0160 (19)0.0315 (19)0.0008 (17)0.0119 (17)0.0037 (16)
N230.036 (2)0.0187 (18)0.036 (2)0.0008 (18)0.0125 (16)0.0008 (17)
C23A0.025 (2)0.021 (2)0.034 (2)0.0003 (19)0.0113 (18)0.0035 (19)
C240.027 (2)0.024 (2)0.043 (3)0.003 (2)0.0117 (19)0.010 (2)
C250.029 (3)0.034 (3)0.030 (2)0.005 (2)0.0047 (19)0.006 (2)
C260.027 (2)0.032 (3)0.026 (2)0.002 (2)0.0066 (18)0.000 (2)
C270.027 (2)0.018 (2)0.033 (2)0.0042 (19)0.0080 (19)0.0001 (18)
C27A0.024 (2)0.017 (2)0.026 (2)0.0017 (18)0.0095 (18)0.0027 (17)
C210.022 (2)0.020 (2)0.027 (2)0.0009 (19)0.0063 (18)0.0019 (18)
N310.027 (2)0.0151 (18)0.0285 (18)0.0031 (15)0.0107 (16)0.0019 (14)
C320.035 (3)0.022 (2)0.032 (2)0.005 (2)0.005 (2)0.0054 (19)
C3210.032 (3)0.024 (2)0.040 (2)0.004 (2)0.008 (2)0.0054 (19)
C330.033 (3)0.017 (2)0.032 (2)0.0057 (19)0.0062 (19)0.0029 (18)
C33A0.022 (2)0.025 (2)0.0216 (19)0.0027 (19)0.0015 (17)0.0040 (18)
C340.033 (3)0.026 (2)0.029 (2)0.008 (2)0.001 (2)0.0040 (19)
C350.030 (3)0.040 (3)0.027 (2)0.003 (2)0.009 (2)0.012 (2)
C360.034 (3)0.027 (3)0.030 (2)0.006 (2)0.011 (2)0.008 (2)
C370.039 (3)0.014 (2)0.025 (2)0.0002 (19)0.0071 (19)0.0031 (17)
C37A0.031 (2)0.021 (2)0.0180 (19)0.0012 (19)0.0036 (18)0.0018 (18)
Geometric parameters (Å, º) top
N1—C7A1.367 (5)N21—N221.369 (5)
N1—N21.380 (5)N21—C27A1.373 (5)
N1—C111.479 (5)N21—C211.471 (5)
N2—N31.290 (5)N22—N231.318 (5)
N3—C3A1.380 (5)N23—C23A1.376 (5)
C3A—C7A1.393 (6)C23A—C241.400 (6)
C3A—C41.420 (6)C23A—C27A1.400 (6)
C4—C51.352 (6)C24—C251.372 (6)
C4—H40.9500C24—H240.9500
C5—C61.421 (6)C25—C261.424 (7)
C5—H50.9500C25—H250.9500
C6—C71.370 (6)C26—C271.361 (6)
C6—H60.9500C26—H260.9500
C7—C7A1.393 (6)C27—C27A1.399 (6)
C7—H70.9500C27—H270.9500
C11—N111.435 (5)C21—N311.434 (5)
C11—H11A0.9900C21—H21A0.9900
C11—H11B0.9900C21—H21B0.9900
N11—C17A1.413 (5)N31—C37A1.420 (5)
N11—C121.494 (5)N31—C321.469 (5)
C12—C1211.500 (6)C32—C3211.499 (6)
C12—C131.553 (6)C32—C331.537 (6)
C12—H121.0000C32—H321.0000
C121—H12A0.9800C321—H32A0.9800
C121—H12B0.9800C321—H32B0.9800
C121—H12C0.9800C321—H32C0.9800
C13—C13A1.505 (6)C33—C33A1.506 (6)
C13—H13A0.9900C33—H33A0.9900
C13—H13B0.9900C33—H33B0.9900
C13A—C141.382 (6)C33A—C341.372 (6)
C13A—C17A1.396 (6)C33A—C37A1.408 (6)
C14—C151.395 (6)C34—C351.388 (6)
C14—H140.9500C34—H340.9500
C15—C161.392 (6)C35—C361.383 (7)
C15—H150.9500C35—H350.9500
C16—C171.398 (5)C36—C371.400 (6)
C16—H160.9500C36—H360.9500
C17—C17A1.387 (6)C37—C37A1.386 (6)
C17—H170.9500C37—H370.9500
C7A—N1—N2109.5 (3)N22—N21—C27A110.2 (3)
C7A—N1—C11131.3 (3)N22—N21—C21118.5 (3)
N2—N1—C11119.2 (3)C27A—N21—C21131.2 (3)
N3—N2—N1109.1 (3)N23—N22—N21108.7 (3)
N2—N3—C3A108.3 (3)N22—N23—C23A107.9 (3)
N3—C3A—C7A109.1 (4)N23—C23A—C24130.0 (4)
N3—C3A—C4130.7 (4)N23—C23A—C27A109.4 (4)
C7A—C3A—C4120.2 (4)C24—C23A—C27A120.5 (4)
C5—C4—C3A117.6 (4)C25—C24—C23A117.9 (4)
C5—C4—H4121.2C25—C24—H24121.0
C3A—C4—H4121.2C23A—C24—H24121.0
C4—C5—C6121.4 (4)C24—C25—C26120.4 (4)
C4—C5—H5119.3C24—C25—H25119.8
C6—C5—H5119.3C26—C25—H25119.8
C7—C6—C5122.0 (4)C27—C26—C25122.7 (4)
C7—C6—H6119.0C27—C26—H26118.7
C5—C6—H6119.0C25—C26—H26118.7
C6—C7—C7A116.6 (4)C26—C27—C27A116.4 (4)
C6—C7—H7121.7C26—C27—H27121.8
C7A—C7—H7121.7C27A—C27—H27121.8
N1—C7A—C7133.7 (4)N21—C27A—C27134.3 (4)
N1—C7A—C3A104.0 (4)N21—C27A—C23A103.7 (3)
C7—C7A—C3A122.2 (4)C27—C27A—C23A122.0 (4)
N11—C11—N1115.9 (3)N31—C21—N21115.6 (3)
N11—C11—H11A108.3N31—C21—H21A108.4
N1—C11—H11A108.3N21—C21—H21A108.4
N11—C11—H11B108.3N31—C21—H21B108.4
N1—C11—H11B108.3N21—C21—H21B108.4
H11A—C11—H11B107.4H21A—C21—H21B107.4
C17A—N11—C11120.3 (3)C37A—N31—C21120.8 (3)
C17A—N11—C12107.6 (3)C37A—N31—C32107.4 (3)
C11—N11—C12120.5 (3)C21—N31—C32121.5 (3)
N11—C12—C121113.5 (3)N31—C32—C321115.3 (4)
N11—C12—C13101.6 (3)N31—C32—C33102.2 (3)
C121—C12—C13114.2 (4)C321—C32—C33114.5 (4)
N11—C12—H12109.1N31—C32—H32108.1
C121—C12—H12109.1C321—C32—H32108.1
C13—C12—H12109.1C33—C32—H32108.1
C12—C121—H12A109.5C32—C321—H32A109.5
C12—C121—H12B109.5C32—C321—H32B109.5
H12A—C121—H12B109.5H32A—C321—H32B109.5
C12—C121—H12C109.5C32—C321—H32C109.5
H12A—C121—H12C109.5H32A—C321—H32C109.5
H12B—C121—H12C109.5H32B—C321—H32C109.5
C13A—C13—C12102.5 (3)C33A—C33—C32102.5 (3)
C13A—C13—H13A111.3C33A—C33—H33A111.3
C12—C13—H13A111.3C32—C33—H33A111.3
C13A—C13—H13B111.3C33A—C33—H33B111.3
C12—C13—H13B111.3C32—C33—H33B111.3
H13A—C13—H13B109.2H33A—C33—H33B109.2
C14—C13A—C17A120.9 (4)C34—C33A—C37A120.2 (4)
C14—C13A—C13130.5 (4)C34—C33A—C33131.9 (4)
C17A—C13A—C13108.6 (4)C37A—C33A—C33107.9 (3)
C13A—C14—C15118.4 (4)C33A—C34—C35119.1 (4)
C13A—C14—H14120.8C33A—C34—H34120.4
C15—C14—H14120.8C35—C34—H34120.4
C16—C15—C14120.6 (4)C36—C35—C34120.7 (4)
C16—C15—H15119.7C36—C35—H35119.6
C14—C15—H15119.7C34—C35—H35119.6
C15—C16—C17121.1 (4)C35—C36—C37121.2 (4)
C15—C16—H16119.4C35—C36—H36119.4
C17—C16—H16119.4C37—C36—H36119.4
C17A—C17—C16117.7 (4)C37A—C37—C36117.5 (4)
C17A—C17—H17121.1C37A—C37—H37121.3
C16—C17—H17121.1C36—C37—H37121.3
C17—C17A—C13A121.2 (4)C37—C37A—C33A121.2 (4)
C17—C17A—N11128.7 (4)C37—C37A—N31129.5 (4)
C13A—C17A—N11110.1 (4)C33A—C37A—N31109.2 (3)
C7A—N1—N2—N30.8 (4)C27A—N21—N22—N230.6 (4)
C11—N1—N2—N3179.0 (3)C21—N21—N22—N23178.0 (3)
N1—N2—N3—C3A1.0 (4)N21—N22—N23—C23A0.8 (4)
N2—N3—C3A—C7A0.8 (4)N22—N23—C23A—C24179.8 (4)
N2—N3—C3A—C4179.7 (4)N22—N23—C23A—C27A0.7 (4)
N3—C3A—C4—C5177.6 (4)N23—C23A—C24—C25179.5 (4)
C7A—C3A—C4—C52.9 (6)C27A—C23A—C24—C250.1 (6)
C3A—C4—C5—C62.3 (6)C23A—C24—C25—C260.9 (6)
C4—C5—C6—C71.4 (7)C24—C25—C26—C270.7 (7)
C5—C6—C7—C7A0.9 (6)C25—C26—C27—C27A0.4 (6)
N2—N1—C7A—C7176.9 (4)N22—N21—C27A—C27178.5 (4)
C11—N1—C7A—C71.0 (8)C21—N21—C27A—C271.5 (7)
N2—N1—C7A—C3A0.3 (4)N22—N21—C27A—C23A0.1 (4)
C11—N1—C7A—C3A178.2 (4)C21—N21—C27A—C23A177.2 (4)
C6—C7—C7A—N1178.3 (4)C26—C27—C27A—N21179.8 (4)
C6—C7—C7A—C3A1.5 (6)C26—C27—C27A—C23A1.4 (6)
N3—C3A—C7A—N10.3 (4)N23—C23A—C27A—N210.3 (4)
C4—C3A—C7A—N1179.8 (4)C24—C23A—C27A—N21179.9 (4)
N3—C3A—C7A—C7177.9 (4)N23—C23A—C27A—C27179.2 (4)
C4—C3A—C7A—C72.6 (6)C24—C23A—C27A—C271.3 (6)
C7A—N1—C11—N1176.8 (5)N22—N21—C21—N31107.6 (4)
N2—N1—C11—N11105.6 (4)C27A—N21—C21—N3175.6 (5)
N1—C11—N11—C17A60.1 (5)N21—C21—N31—C37A64.4 (5)
N1—C11—N11—C1278.5 (5)N21—C21—N31—C3276.5 (5)
C17A—N11—C12—C121152.6 (3)C37A—N31—C32—C321156.6 (4)
C11—N11—C12—C12164.2 (5)C21—N31—C32—C32158.1 (5)
C17A—N11—C12—C1329.5 (4)C37A—N31—C32—C3331.6 (4)
C11—N11—C12—C13172.7 (3)C21—N31—C32—C33177.0 (4)
N11—C12—C13—C13A29.0 (4)N31—C32—C33—C33A30.7 (4)
C121—C12—C13—C13A151.6 (4)C321—C32—C33—C33A156.1 (4)
C12—C13—C13A—C14162.9 (4)C32—C33—C33A—C34160.0 (5)
C12—C13—C13A—C17A19.7 (5)C32—C33—C33A—C37A20.0 (4)
C17A—C13A—C14—C150.1 (6)C37A—C33A—C34—C351.0 (6)
C13—C13A—C14—C15177.3 (4)C33—C33A—C34—C35179.0 (4)
C13A—C14—C15—C160.2 (6)C33A—C34—C35—C361.0 (6)
C14—C15—C16—C170.1 (6)C34—C35—C36—C371.3 (6)
C15—C16—C17—C17A0.1 (6)C35—C36—C37—C37A0.4 (6)
C16—C17—C17A—C13A0.1 (6)C36—C37—C37A—C33A2.5 (6)
C16—C17—C17A—N11179.3 (4)C36—C37—C37A—N31179.9 (4)
C14—C13A—C17A—C170.0 (6)C34—C33A—C37A—C372.8 (6)
C13—C13A—C17A—C17177.7 (3)C33—C33A—C37A—C37177.2 (4)
C14—C13A—C17A—N11179.3 (3)C34—C33A—C37A—N31179.1 (4)
C13—C13A—C17A—N111.6 (5)C33—C33A—C37A—N310.9 (5)
C11—N11—C17A—C1719.0 (6)C21—N31—C37A—C3716.4 (6)
C12—N11—C17A—C17162.3 (4)C32—N31—C37A—C37162.1 (4)
C11—N11—C17A—C13A161.8 (4)C21—N31—C37A—C33A165.7 (4)
C12—N11—C17A—C13A18.4 (4)C32—N31—C37A—C33A20.1 (4)

Experimental details

Crystal data
Chemical formulaC16H16N4
Mr264.33
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)7.5660 (3), 17.7842 (8), 10.2284 (4)
β (°) 104.689 (3)
V3)1331.30 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.15 × 0.10 × 0.03
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.988, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
10746, 3086, 2083
Rint0.074
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.146, 0.98
No. of reflections3086
No. of parameters363
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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