The molecular structure of the title compound, C
20H
23N
5, shows two strong intramolecular N—H
N hydrogen bonds. In contrast, intermolecular interactions are weak.
Supporting information
CCDC reference: 236090
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.124
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. N1 = 2.65 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N-(8-Quinolyl)-
o-(1,1,3,3-tetramethylguanidino)phenylamine
top
Crystal data top
C20H23N5 | F(000) = 712 |
Mr = 333.43 | Dx = 1.216 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2842 (5) Å | Cell parameters from 2544 reflections |
b = 12.2427 (7) Å | θ = 2.2–25.8° |
c = 16.3490 (9) Å | µ = 0.08 mm−1 |
β = 101.463 (1)° | T = 120 K |
V = 1821.22 (17) Å3 | Prism, pale yellow |
Z = 4 | 0.32 × 0.25 × 0.18 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4531 independent reflections |
Radiation source: sealed tube | 3494 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→12 |
Tmin = 0.922, Tmax = 0.991 | k = −16→16 |
14968 measured reflections | l = −21→21 |
Refinement top
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)] = 0.049 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3663P] where P = (Fo2 + 2Fc2)/3 |
4531 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N3 | 0.42210 (13) | 0.63483 (9) | 0.29654 (7) | 0.0295 (3) | |
N2 | 0.25913 (12) | 0.67559 (9) | 0.14499 (7) | 0.0249 (3) | |
H2 | 0.2365 | 0.6956 | 0.1926 | 0.030* | |
N1 | 0.04089 (11) | 0.80379 (9) | 0.16928 (7) | 0.0223 (2) | |
N4 | −0.21170 (12) | 0.75418 (10) | 0.13448 (7) | 0.0280 (3) | |
N5 | −0.12057 (12) | 0.85341 (10) | 0.25298 (7) | 0.0289 (3) | |
C1 | 0.45011 (13) | 0.57368 (10) | 0.23198 (8) | 0.0227 (3) | |
C2 | 0.50340 (17) | 0.61629 (13) | 0.37074 (9) | 0.0378 (4) | |
H2A | 0.4837 | 0.6577 | 0.4164 | 0.045* | |
C3 | 0.61758 (17) | 0.53906 (13) | 0.38666 (10) | 0.0403 (4) | |
H3A | 0.6737 | 0.5298 | 0.4415 | 0.048* | |
C4 | 0.64654 (15) | 0.47789 (12) | 0.32264 (10) | 0.0350 (3) | |
H4A | 0.7240 | 0.4259 | 0.3321 | 0.042* | |
C5 | 0.56097 (14) | 0.49200 (11) | 0.24208 (9) | 0.0263 (3) | |
C6 | 0.57809 (15) | 0.42706 (11) | 0.17269 (10) | 0.0302 (3) | |
H6A | 0.6531 | 0.3732 | 0.1785 | 0.036* | |
C7 | 0.48608 (15) | 0.44270 (11) | 0.09793 (9) | 0.0286 (3) | |
H7A | 0.4949 | 0.3969 | 0.0523 | 0.034* | |
C8 | 0.37819 (15) | 0.52482 (11) | 0.08631 (8) | 0.0250 (3) | |
H8A | 0.3162 | 0.5337 | 0.0330 | 0.030* | |
C9 | 0.36070 (13) | 0.59280 (10) | 0.15091 (8) | 0.0217 (3) | |
C10 | 0.18640 (14) | 0.73279 (10) | 0.07506 (8) | 0.0214 (3) | |
C11 | 0.22925 (15) | 0.73630 (11) | −0.00180 (8) | 0.0282 (3) | |
H11A | 0.3121 | 0.6952 | −0.0099 | 0.034* | |
C12 | 0.15262 (17) | 0.79906 (12) | −0.06678 (9) | 0.0316 (3) | |
H12A | 0.1825 | 0.8002 | −0.1191 | 0.038* | |
C13 | 0.03300 (16) | 0.85980 (12) | −0.05547 (9) | 0.0316 (3) | |
H13A | −0.0205 | 0.9020 | −0.1001 | 0.038* | |
C14 | −0.00867 (15) | 0.85889 (11) | 0.02134 (8) | 0.0268 (3) | |
H14A | −0.0903 | 0.9018 | 0.0289 | 0.032* | |
C15 | 0.06566 (13) | 0.79686 (10) | 0.08762 (8) | 0.0210 (3) | |
C16 | −0.09234 (14) | 0.80360 (10) | 0.18338 (8) | 0.0227 (3) | |
C17 | −0.19522 (18) | 0.66038 (12) | 0.08323 (9) | 0.0363 (4) | |
H17A | −0.2087 | 0.6830 | 0.0247 | 0.054* | |
H17B | −0.2691 | 0.6053 | 0.0891 | 0.054* | |
H17C | −0.0967 | 0.6294 | 0.1012 | 0.054* | |
C18 | −0.35621 (15) | 0.80492 (15) | 0.11890 (10) | 0.0394 (4) | |
H18A | −0.3499 | 0.8766 | 0.1461 | 0.059* | |
H18B | −0.4250 | 0.7585 | 0.1415 | 0.059* | |
H18C | −0.3911 | 0.8139 | 0.0587 | 0.059* | |
C19 | −0.01958 (17) | 0.93486 (13) | 0.29569 (10) | 0.0384 (4) | |
H19A | 0.0515 | 0.8998 | 0.3403 | 0.058* | |
H19B | −0.0746 | 0.9906 | 0.3197 | 0.058* | |
H19C | 0.0326 | 0.9692 | 0.2559 | 0.058* | |
C20 | −0.22145 (17) | 0.80620 (14) | 0.30104 (9) | 0.0365 (4) | |
H20A | −0.2587 | 0.7364 | 0.2761 | 0.055* | |
H20B | −0.3038 | 0.8564 | 0.3007 | 0.055* | |
H20C | −0.1697 | 0.7941 | 0.3586 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N3 | 0.0284 (6) | 0.0296 (6) | 0.0276 (6) | 0.0032 (5) | −0.0011 (5) | −0.0043 (5) |
N2 | 0.0248 (6) | 0.0297 (6) | 0.0209 (5) | 0.0099 (5) | 0.0060 (4) | −0.0010 (4) |
N1 | 0.0182 (5) | 0.0243 (6) | 0.0243 (6) | 0.0024 (4) | 0.0040 (4) | −0.0049 (4) |
N4 | 0.0202 (6) | 0.0323 (6) | 0.0312 (6) | −0.0030 (5) | 0.0046 (5) | −0.0041 (5) |
N5 | 0.0240 (6) | 0.0333 (6) | 0.0312 (6) | 0.0029 (5) | 0.0096 (5) | −0.0084 (5) |
C1 | 0.0177 (6) | 0.0211 (6) | 0.0293 (7) | −0.0009 (5) | 0.0046 (5) | −0.0008 (5) |
C2 | 0.0391 (9) | 0.0385 (9) | 0.0309 (8) | 0.0017 (7) | −0.0053 (6) | −0.0049 (6) |
C3 | 0.0342 (8) | 0.0407 (9) | 0.0377 (8) | −0.0027 (7) | −0.0129 (7) | 0.0050 (7) |
C4 | 0.0207 (7) | 0.0287 (7) | 0.0516 (9) | 0.0018 (6) | −0.0021 (6) | 0.0081 (7) |
C5 | 0.0172 (6) | 0.0218 (6) | 0.0400 (8) | −0.0011 (5) | 0.0056 (5) | 0.0051 (6) |
C6 | 0.0238 (7) | 0.0207 (7) | 0.0504 (9) | 0.0053 (5) | 0.0182 (6) | 0.0047 (6) |
C7 | 0.0326 (7) | 0.0217 (6) | 0.0376 (8) | 0.0005 (5) | 0.0219 (6) | −0.0006 (6) |
C8 | 0.0260 (7) | 0.0256 (7) | 0.0257 (7) | 0.0001 (5) | 0.0108 (5) | 0.0008 (5) |
C9 | 0.0169 (6) | 0.0215 (6) | 0.0279 (7) | 0.0007 (5) | 0.0073 (5) | 0.0001 (5) |
C10 | 0.0195 (6) | 0.0213 (6) | 0.0232 (6) | 0.0004 (5) | 0.0038 (5) | −0.0019 (5) |
C11 | 0.0271 (7) | 0.0303 (7) | 0.0288 (7) | 0.0050 (6) | 0.0096 (6) | −0.0001 (6) |
C12 | 0.0367 (8) | 0.0335 (8) | 0.0261 (7) | 0.0003 (6) | 0.0097 (6) | 0.0020 (6) |
C13 | 0.0347 (8) | 0.0293 (7) | 0.0284 (7) | 0.0016 (6) | 0.0003 (6) | 0.0065 (6) |
C14 | 0.0228 (6) | 0.0240 (7) | 0.0327 (7) | 0.0030 (5) | 0.0031 (6) | 0.0000 (6) |
C15 | 0.0180 (6) | 0.0197 (6) | 0.0247 (6) | −0.0025 (5) | 0.0028 (5) | −0.0050 (5) |
C16 | 0.0216 (6) | 0.0198 (6) | 0.0262 (6) | 0.0042 (5) | 0.0038 (5) | −0.0013 (5) |
C17 | 0.0425 (9) | 0.0323 (8) | 0.0343 (8) | −0.0155 (7) | 0.0084 (7) | −0.0065 (6) |
C18 | 0.0197 (7) | 0.0559 (10) | 0.0404 (9) | −0.0013 (7) | 0.0007 (6) | 0.0088 (7) |
C19 | 0.0359 (8) | 0.0396 (9) | 0.0394 (9) | 0.0036 (7) | 0.0067 (7) | −0.0178 (7) |
C20 | 0.0327 (8) | 0.0475 (9) | 0.0323 (8) | 0.0099 (7) | 0.0139 (6) | 0.0029 (7) |
Geometric parameters (Å, º) top
N3—C2 | 1.3149 (18) | C7—H7A | 0.9500 |
N3—C1 | 1.3606 (17) | C8—C9 | 1.3794 (18) |
N2—C9 | 1.3746 (16) | C8—H8A | 0.9500 |
N2—C10 | 1.3952 (16) | C10—C11 | 1.3921 (18) |
N2—H2 | 0.8800 | C10—C15 | 1.4161 (17) |
N1—C16 | 1.3025 (16) | C11—C12 | 1.387 (2) |
N1—C15 | 1.4017 (16) | C11—H11A | 0.9500 |
N4—C16 | 1.3715 (17) | C12—C13 | 1.379 (2) |
N4—C17 | 1.4474 (18) | C12—H12A | 0.9500 |
N4—C18 | 1.4543 (18) | C13—C14 | 1.386 (2) |
N5—C16 | 1.3616 (16) | C13—H13A | 0.9500 |
N5—C19 | 1.4494 (19) | C14—C15 | 1.3891 (18) |
N5—C20 | 1.4564 (18) | C14—H14A | 0.9500 |
C1—C5 | 1.4209 (17) | C17—H17A | 0.9800 |
C1—C9 | 1.4364 (18) | C17—H17B | 0.9800 |
C2—C3 | 1.406 (2) | C17—H17C | 0.9800 |
C2—H2A | 0.9500 | C18—H18A | 0.9800 |
C3—C4 | 1.357 (2) | C18—H18B | 0.9800 |
C3—H3A | 0.9500 | C18—H18C | 0.9800 |
C4—C5 | 1.407 (2) | C19—H19A | 0.9800 |
C4—H4A | 0.9500 | C19—H19B | 0.9800 |
C5—C6 | 1.420 (2) | C19—H19C | 0.9800 |
C6—C7 | 1.358 (2) | C20—H20A | 0.9800 |
C6—H6A | 0.9500 | C20—H20B | 0.9800 |
C7—C8 | 1.4052 (18) | C20—H20C | 0.9800 |
| | | |
C2—N3—C1 | 117.23 (12) | C12—C11—H11A | 119.6 |
C9—N2—C10 | 129.89 (11) | C10—C11—H11A | 119.6 |
C9—N2—H2 | 115.1 | C13—C12—C11 | 120.00 (13) |
C10—N2—H2 | 115.1 | C13—C12—H12A | 120.0 |
C16—N1—C15 | 120.65 (11) | C11—C12—H12A | 120.0 |
C16—N4—C17 | 121.42 (12) | C12—C13—C14 | 119.64 (13) |
C16—N4—C18 | 121.60 (12) | C12—C13—H13A | 120.2 |
C17—N4—C18 | 115.95 (12) | C14—C13—H13A | 120.2 |
C16—N5—C19 | 119.82 (11) | C13—C14—C15 | 121.76 (13) |
C16—N5—C20 | 121.62 (12) | C13—C14—H14A | 119.1 |
C19—N5—C20 | 115.91 (12) | C15—C14—H14A | 119.1 |
N3—C1—C5 | 122.87 (12) | C14—C15—N1 | 124.03 (12) |
N3—C1—C9 | 117.49 (11) | C14—C15—C10 | 118.33 (12) |
C5—C1—C9 | 119.63 (12) | N1—C15—C10 | 117.14 (11) |
N3—C2—C3 | 124.09 (15) | N1—C16—N5 | 119.63 (12) |
N3—C2—H2A | 118.0 | N1—C16—N4 | 125.68 (12) |
C3—C2—H2A | 118.0 | N5—C16—N4 | 114.67 (11) |
C4—C3—C2 | 119.10 (14) | N4—C17—H17A | 109.5 |
C4—C3—H3A | 120.5 | N4—C17—H17B | 109.5 |
C2—C3—H3A | 120.5 | H17A—C17—H17B | 109.5 |
C3—C4—C5 | 119.53 (13) | N4—C17—H17C | 109.5 |
C3—C4—H4A | 120.2 | H17A—C17—H17C | 109.5 |
C5—C4—H4A | 120.2 | H17B—C17—H17C | 109.5 |
C4—C5—C6 | 123.17 (13) | N4—C18—H18A | 109.5 |
C4—C5—C1 | 117.15 (13) | N4—C18—H18B | 109.5 |
C6—C5—C1 | 119.65 (13) | H18A—C18—H18B | 109.5 |
C7—C6—C5 | 119.32 (12) | N4—C18—H18C | 109.5 |
C7—C6—H6A | 120.3 | H18A—C18—H18C | 109.5 |
C5—C6—H6A | 120.3 | H18B—C18—H18C | 109.5 |
C6—C7—C8 | 121.76 (12) | N5—C19—H19A | 109.5 |
C6—C7—H7A | 119.1 | N5—C19—H19B | 109.5 |
C8—C7—H7A | 119.1 | H19A—C19—H19B | 109.5 |
C9—C8—C7 | 121.16 (13) | N5—C19—H19C | 109.5 |
C9—C8—H8A | 119.4 | H19A—C19—H19C | 109.5 |
C7—C8—H8A | 119.4 | H19B—C19—H19C | 109.5 |
N2—C9—C8 | 125.06 (12) | N5—C20—H20A | 109.5 |
N2—C9—C1 | 116.60 (11) | N5—C20—H20B | 109.5 |
C8—C9—C1 | 118.28 (12) | H20A—C20—H20B | 109.5 |
C11—C10—N2 | 125.21 (12) | N5—C20—H20C | 109.5 |
C11—C10—C15 | 119.36 (12) | H20A—C20—H20C | 109.5 |
N2—C10—C15 | 115.30 (11) | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 120.88 (13) | | |
| | | |
C2—N3—C1—C5 | 0.4 (2) | C9—N2—C10—C15 | 166.96 (12) |
C2—N3—C1—C9 | 179.40 (12) | N2—C10—C11—C12 | −177.51 (13) |
C1—N3—C2—C3 | 1.0 (2) | C15—C10—C11—C12 | −1.9 (2) |
N3—C2—C3—C4 | −0.9 (2) | C10—C11—C12—C13 | 0.6 (2) |
C2—C3—C4—C5 | −0.7 (2) | C11—C12—C13—C14 | 0.9 (2) |
C3—C4—C5—C6 | −176.16 (14) | C12—C13—C14—C15 | −1.0 (2) |
C3—C4—C5—C1 | 2.0 (2) | C13—C14—C15—N1 | 171.25 (12) |
N3—C1—C5—C4 | −1.92 (19) | C13—C14—C15—C10 | −0.41 (19) |
C9—C1—C5—C4 | 179.13 (12) | C16—N1—C15—C14 | 46.76 (18) |
N3—C1—C5—C6 | 176.32 (12) | C16—N1—C15—C10 | −141.49 (12) |
C9—C1—C5—C6 | −2.63 (18) | C11—C10—C15—C14 | 1.84 (18) |
C4—C5—C6—C7 | 176.86 (13) | N2—C10—C15—C14 | 177.85 (11) |
C1—C5—C6—C7 | −1.26 (19) | C11—C10—C15—N1 | −170.40 (12) |
C5—C6—C7—C8 | 2.8 (2) | N2—C10—C15—N1 | 5.60 (16) |
C6—C7—C8—C9 | −0.4 (2) | C15—N1—C16—N5 | −153.01 (12) |
C10—N2—C9—C8 | −22.2 (2) | C15—N1—C16—N4 | 28.7 (2) |
C10—N2—C9—C1 | 160.72 (12) | C19—N5—C16—N1 | 20.16 (19) |
C7—C8—C9—N2 | 179.46 (12) | C20—N5—C16—N1 | −140.62 (13) |
C7—C8—C9—C1 | −3.50 (18) | C19—N5—C16—N4 | −161.38 (13) |
N3—C1—C9—N2 | 3.24 (17) | C20—N5—C16—N4 | 37.84 (18) |
C5—C1—C9—N2 | −177.75 (11) | C17—N4—C16—N1 | 26.8 (2) |
N3—C1—C9—C8 | −174.05 (12) | C18—N4—C16—N1 | −141.06 (14) |
C5—C1—C9—C8 | 4.95 (18) | C17—N4—C16—N5 | −151.51 (12) |
C9—N2—C10—C11 | −17.3 (2) | C18—N4—C16—N5 | 40.59 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N1 | 0.88 | 2.22 | 2.6545 (14) | 110 |
N2—H2···N3 | 0.88 | 2.29 | 2.6808 (16) | 107 |
C4—H4A···N1i | 0.95 | 2.65 | 3.5818 (18) | 167 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |