The title compound, C
9H
10N
2, crystallizes with two formula units in the asymmetric unit. When viewed along the
b axis, the two crystallographically unique molecules form alternating columns along
a. Within each column, the molecules are linked by N—H
N hydrogen bonds to form infinite chains. Intermolecular C
C and C
N distances suggest that molecules in adjacent columns are linked primarily by C—H
π interactions, with little, if any, π stacking. Metric parameters for the imidazoline fragments are comparable to those of other 2-substituted imidazoline species.
Supporting information
CCDC reference: 238772
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.158
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.876 1.000
Tmin' and Tmax expected: 0.973 0.991
RR' = 0.893
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
PLAT351_ALERT_3_C Long C-H Bond (0.96A) C34 - H34A ... 1.14 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Crystal data top
C9H10N2 | F(000) = 624 |
Mr = 146.19 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/n | Melting point = 359–361 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 13.4996 (6) Å | Cell parameters from 911 reflections |
b = 5.1922 (2) Å | θ = 3.7–22.0° |
c = 22.4019 (13) Å | µ = 0.08 mm−1 |
β = 95.880 (4)° | T = 295 K |
V = 1561.95 (13) Å3 | Block, colorless |
Z = 8 | 0.36 × 0.22 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2714 independent reflections |
Radiation source: fine-focus sealed tube | 1894 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | h = −16→16 |
Tmin = 0.876, Tmax = 1.00 | k = −6→6 |
11084 measured reflections | l = −26→26 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.086P)2 + 0.4484P] where P = (Fo2 + 2Fc2)/3 |
2714 reflections | (Δ/σ)max < 0.001 |
239 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 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 | |
C12 | 0.12068 (15) | 0.6192 (4) | 0.09217 (11) | 0.0421 (5) | |
N11 | 0.14360 (16) | 0.4154 (4) | 0.05783 (10) | 0.0536 (6) | |
N13 | 0.11123 (15) | 0.8380 (4) | 0.06539 (9) | 0.0529 (5) | |
C21 | 0.11066 (15) | 0.5837 (4) | 0.15672 (11) | 0.0432 (6) | |
C14 | 0.1274 (3) | 0.7918 (5) | 0.00251 (13) | 0.0589 (7) | |
C22 | 0.15421 (19) | 0.3771 (5) | 0.18878 (12) | 0.0565 (7) | |
H22 | 0.1905 | 0.2569 | 0.1693 | 0.068* | |
C23 | 0.1446 (2) | 0.3473 (6) | 0.24839 (13) | 0.0705 (8) | |
H23 | 0.1751 | 0.2093 | 0.2694 | 0.085* | |
C15 | 0.1383 (2) | 0.4994 (5) | −0.00433 (12) | 0.0553 (7) | |
C26 | 0.05650 (17) | 0.7591 (5) | 0.18666 (12) | 0.0541 (7) | |
H26 | 0.0270 | 0.8995 | 0.1661 | 0.065* | |
C25 | 0.0461 (2) | 0.7272 (6) | 0.24672 (13) | 0.0675 (8) | |
H25 | 0.0092 | 0.8455 | 0.2665 | 0.081* | |
C24 | 0.0896 (2) | 0.5221 (6) | 0.27744 (13) | 0.0730 (8) | |
H24 | 0.0822 | 0.5007 | 0.3180 | 0.088* | |
C32 | 0.54476 (16) | 0.3830 (4) | 0.10091 (10) | 0.0411 (5) | |
N33 | 0.49872 (14) | 0.5990 (4) | 0.09710 (9) | 0.0531 (6) | |
N31 | 0.49496 (15) | 0.1777 (4) | 0.07465 (10) | 0.0563 (6) | |
C41 | 0.64778 (16) | 0.3518 (4) | 0.12911 (10) | 0.0419 (5) | |
C42 | 0.70674 (18) | 0.1474 (5) | 0.11467 (11) | 0.0525 (6) | |
H42 | 0.6805 | 0.0236 | 0.0875 | 0.063* | |
C34 | 0.3986 (2) | 0.5487 (5) | 0.06567 (16) | 0.0625 (7) | |
C44 | 0.84322 (19) | 0.3038 (5) | 0.18023 (12) | 0.0598 (7) | |
H44 | 0.9090 | 0.2897 | 0.1969 | 0.072* | |
C43 | 0.80368 (18) | 0.1250 (5) | 0.13998 (12) | 0.0578 (7) | |
H43 | 0.8424 | −0.0128 | 0.1296 | 0.069* | |
C46 | 0.68795 (18) | 0.5311 (5) | 0.17053 (11) | 0.0539 (6) | |
H46 | 0.6495 | 0.6690 | 0.1812 | 0.065* | |
C35 | 0.3943 (2) | 0.2576 (5) | 0.05340 (15) | 0.0607 (7) | |
C45 | 0.78476 (19) | 0.5056 (5) | 0.19599 (13) | 0.0635 (7) | |
H45 | 0.8110 | 0.6258 | 0.2241 | 0.076* | |
H11 | 0.124 (2) | 0.260 (7) | 0.0641 (13) | 0.083 (10)* | |
H31 | 0.5115 (18) | 0.017 (6) | 0.0887 (11) | 0.067 (8)* | |
H15B | 0.0797 (19) | 0.427 (5) | −0.0289 (11) | 0.062 (7)* | |
H14A | 0.182 (2) | 0.868 (5) | −0.0097 (12) | 0.068 (8)* | |
H15A | 0.194 (2) | 0.455 (5) | −0.0251 (12) | 0.070 (8)* | |
H14B | 0.072 (2) | 0.859 (5) | −0.0270 (12) | 0.068 (8)* | |
H34B | 0.389 (2) | 0.644 (6) | 0.0289 (14) | 0.081 (10)* | |
H35B | 0.369 (3) | 0.222 (8) | 0.0083 (16) | 0.124 (13)* | |
H35A | 0.345 (2) | 0.179 (6) | 0.0828 (13) | 0.087 (9)* | |
H34A | 0.348 (3) | 0.604 (7) | 0.1015 (15) | 0.118 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C12 | 0.0379 (11) | 0.0329 (12) | 0.0550 (15) | −0.0003 (9) | 0.0024 (10) | −0.0039 (10) |
N11 | 0.0689 (14) | 0.0353 (12) | 0.0578 (15) | −0.0017 (10) | 0.0121 (10) | −0.0034 (10) |
N13 | 0.0706 (13) | 0.0361 (11) | 0.0527 (13) | 0.0044 (9) | 0.0098 (10) | 0.0007 (9) |
C21 | 0.0399 (12) | 0.0370 (12) | 0.0521 (15) | −0.0056 (9) | 0.0014 (10) | −0.0018 (10) |
C14 | 0.0760 (19) | 0.0469 (15) | 0.0548 (18) | −0.0011 (14) | 0.0117 (15) | 0.0019 (12) |
C22 | 0.0617 (15) | 0.0451 (14) | 0.0613 (18) | 0.0047 (12) | −0.0001 (12) | 0.0000 (12) |
C23 | 0.091 (2) | 0.0601 (17) | 0.0568 (19) | −0.0022 (15) | −0.0086 (15) | 0.0118 (14) |
C15 | 0.0626 (16) | 0.0492 (15) | 0.0548 (18) | −0.0012 (13) | 0.0096 (14) | −0.0062 (12) |
C26 | 0.0541 (14) | 0.0467 (14) | 0.0622 (18) | 0.0013 (11) | 0.0094 (12) | −0.0025 (12) |
C25 | 0.0739 (18) | 0.0660 (18) | 0.066 (2) | −0.0047 (14) | 0.0229 (14) | −0.0108 (15) |
C24 | 0.093 (2) | 0.076 (2) | 0.0499 (18) | −0.0206 (17) | 0.0080 (15) | −0.0034 (16) |
C32 | 0.0504 (13) | 0.0319 (12) | 0.0414 (13) | −0.0037 (10) | 0.0064 (10) | 0.0001 (9) |
N33 | 0.0545 (12) | 0.0366 (11) | 0.0660 (14) | −0.0013 (9) | −0.0041 (10) | −0.0023 (9) |
N31 | 0.0580 (13) | 0.0330 (11) | 0.0747 (16) | −0.0019 (9) | −0.0086 (10) | −0.0043 (10) |
C41 | 0.0494 (13) | 0.0336 (11) | 0.0431 (13) | −0.0045 (10) | 0.0074 (10) | 0.0029 (10) |
C42 | 0.0572 (15) | 0.0486 (14) | 0.0516 (16) | −0.0002 (11) | 0.0059 (11) | −0.0060 (11) |
C34 | 0.0587 (16) | 0.0438 (15) | 0.081 (2) | −0.0018 (12) | −0.0099 (15) | −0.0008 (14) |
C44 | 0.0484 (14) | 0.0603 (16) | 0.0692 (19) | −0.0030 (12) | −0.0015 (12) | 0.0101 (14) |
C43 | 0.0529 (15) | 0.0545 (16) | 0.0668 (18) | 0.0085 (12) | 0.0089 (12) | 0.0006 (13) |
C46 | 0.0587 (15) | 0.0399 (13) | 0.0621 (17) | −0.0018 (11) | 0.0014 (12) | −0.0040 (12) |
C35 | 0.0566 (16) | 0.0442 (15) | 0.078 (2) | −0.0022 (12) | −0.0091 (14) | −0.0036 (13) |
C45 | 0.0638 (16) | 0.0501 (15) | 0.0734 (19) | −0.0108 (13) | −0.0082 (13) | −0.0061 (14) |
Geometric parameters (Å, º) top
N11—C12 | 1.362 (3) | C26—C25 | 1.377 (4) |
N13—C12 | 1.285 (3) | C26—H26 | 0.9300 |
N11—C15 | 1.454 (3) | C25—C24 | 1.368 (4) |
N13—C14 | 1.467 (3) | C25—H25 | 0.9300 |
C14—C15 | 1.534 (4) | C24—H24 | 0.9300 |
N31—C32 | 1.361 (3) | C32—C41 | 1.476 (3) |
N33—C32 | 1.280 (3) | N31—H31 | 0.91 (3) |
N31—C35 | 1.454 (3) | C41—C42 | 1.385 (3) |
N33—C34 | 1.482 (3) | C41—C46 | 1.385 (3) |
C34—C35 | 1.537 (4) | C42—C43 | 1.377 (3) |
C12—C21 | 1.478 (3) | C42—H42 | 0.9300 |
N11—H11 | 0.87 (3) | C34—C35 | 1.537 (4) |
C21—C26 | 1.384 (3) | C34—H34B | 0.96 (3) |
C21—C22 | 1.388 (3) | C34—H34A | 1.14 (4) |
C14—C15 | 1.534 (4) | C44—C43 | 1.364 (4) |
C14—H14A | 0.90 (3) | C44—C45 | 1.379 (4) |
C14—H14B | 1.01 (3) | C44—H44 | 0.9300 |
C22—C23 | 1.364 (4) | C43—H43 | 0.9300 |
C22—H22 | 0.9300 | C46—C45 | 1.378 (3) |
C23—C24 | 1.377 (4) | C46—H46 | 0.9300 |
C23—H23 | 0.9300 | C35—H35B | 1.05 (4) |
C15—H15B | 0.99 (3) | C35—H35A | 1.07 (3) |
C15—H15A | 0.95 (3) | C45—H45 | 0.9300 |
| | | |
N13—C12—N11 | 116.1 (2) | N33—C32—N31 | 116.2 (2) |
N13—C12—C21 | 123.5 (2) | N33—C32—C41 | 123.65 (19) |
N11—C12—C21 | 120.3 (2) | N31—C32—C41 | 120.05 (19) |
C12—N11—C15 | 108.4 (2) | C32—N33—C34 | 106.88 (19) |
C12—N11—H11 | 123 (2) | C32—N31—C35 | 108.8 (2) |
C15—N11—H11 | 117 (2) | C32—N31—H31 | 118.3 (16) |
C12—N13—C14 | 106.62 (19) | C35—N31—H31 | 124.2 (16) |
C26—C21—C22 | 118.3 (2) | C42—C41—C46 | 118.5 (2) |
C26—C21—C12 | 119.9 (2) | C42—C41—C32 | 121.5 (2) |
C22—C21—C12 | 121.8 (2) | C46—C41—C32 | 120.0 (2) |
N13—C14—C15 | 106.5 (2) | C43—C42—C41 | 120.9 (2) |
N13—C14—H14A | 115.2 (18) | C43—C42—H42 | 119.6 |
C15—C14—H14A | 108.2 (17) | C41—C42—H42 | 119.6 |
N13—C14—H14B | 113.5 (15) | N33—C34—C35 | 105.9 (2) |
C15—C14—H14B | 110.4 (15) | N33—C34—H34B | 110.6 (18) |
H14A—C14—H14B | 103 (2) | C35—C34—H34B | 110.8 (18) |
C23—C22—C21 | 121.1 (2) | N33—C34—H34A | 101.8 (17) |
C23—C22—H22 | 119.4 | C35—C34—H34A | 110.9 (18) |
C21—C22—H22 | 119.4 | H34B—C34—H34A | 116 (3) |
C22—C23—C24 | 119.9 (3) | C43—C44—C45 | 119.4 (2) |
C22—C23—H23 | 120.1 | C43—C44—H44 | 120.3 |
C24—C23—H23 | 120.1 | C45—C44—H44 | 120.3 |
N11—C15—C14 | 101.3 (2) | C44—C43—C42 | 120.4 (2) |
N11—C15—H15B | 112.1 (15) | C44—C43—H43 | 119.8 |
C14—C15—H15B | 110.6 (15) | C42—C43—H43 | 119.8 |
N11—C15—H15A | 115.6 (16) | C45—C46—C41 | 120.2 (2) |
C14—C15—H15A | 112.0 (17) | C45—C46—H46 | 119.9 |
H15B—C15—H15A | 105 (2) | C41—C46—H46 | 119.9 |
C25—C26—C21 | 120.4 (2) | N31—C35—C34 | 101.8 (2) |
C25—C26—H26 | 119.8 | N31—C35—H35B | 118 (2) |
C21—C26—H26 | 119.8 | C34—C35—H35B | 111 (2) |
C24—C25—C26 | 120.2 (3) | N31—C35—H35A | 108.2 (16) |
C24—C25—H25 | 119.9 | C34—C35—H35A | 106.2 (17) |
C26—C25—H25 | 119.9 | H35B—C35—H35A | 112 (3) |
C25—C24—C23 | 120.0 (3) | C46—C45—C44 | 120.7 (2) |
C25—C24—H24 | 120.0 | C46—C45—H45 | 119.7 |
C23—C24—H24 | 120.0 | C44—C45—H45 | 119.7 |
| | | |
N13—C12—N11—C15 | −7.5 (3) | N31—C32—N33—C34 | 2.5 (3) |
C21—C12—N11—C15 | 174.1 (2) | C41—C32—N33—C34 | 179.6 (2) |
N11—C12—N13—C14 | 1.1 (3) | N33—C32—N31—C35 | −5.8 (3) |
C21—C12—N13—C14 | 179.5 (2) | C41—C32—N31—C35 | 177.0 (2) |
N13—C12—C21—C26 | 23.4 (3) | N33—C32—C41—C42 | −156.9 (2) |
N11—C12—C21—C26 | −158.3 (2) | N31—C32—C41—C42 | 20.1 (3) |
N13—C12—C21—C22 | −156.7 (2) | N33—C32—C41—C46 | 22.4 (3) |
N11—C12—C21—C22 | 21.6 (3) | N31—C32—C41—C46 | −160.7 (2) |
C12—N13—C14—C15 | 5.3 (3) | C46—C41—C42—C43 | −1.2 (4) |
C26—C21—C22—C23 | −0.4 (3) | C32—C41—C42—C43 | 178.0 (2) |
C12—C21—C22—C23 | 179.8 (2) | C32—N33—C34—C35 | 1.6 (3) |
C21—C22—C23—C24 | 1.0 (4) | C45—C44—C43—C42 | 0.9 (4) |
C12—N11—C15—C14 | 9.7 (3) | C41—C42—C43—C44 | 0.5 (4) |
N13—C14—C15—N11 | −9.0 (3) | C42—C41—C46—C45 | 0.6 (3) |
C22—C21—C26—C25 | −0.3 (3) | C32—C41—C46—C45 | −178.6 (2) |
C12—C21—C26—C25 | 179.6 (2) | C32—N31—C35—C34 | 6.0 (3) |
C21—C26—C25—C24 | 0.3 (4) | N33—C34—C35—N31 | −4.5 (3) |
C26—C25—C24—C23 | 0.3 (4) | C41—C46—C45—C44 | 0.7 (4) |
C22—C23—C24—C25 | −1.0 (4) | C43—C44—C45—C46 | −1.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N13i | 0.87 (4) | 2.20 (4) | 3.037 (3) | 163 (3) |
N31—H31···N33i | 0.91 (3) | 2.19 (3) | 3.046 (3) | 157 (2) |
Symmetry code: (i) x, y−1, z. |