Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012886/bt6168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012886/bt6168Isup2.hkl |
CCDC reference: 193769
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.186
- Data-to-parameter ratio = 16.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(1) - H(1) ? General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.066 Tmax scaled 0.996 Tmin scaled 0.951
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 and CELDIM in CAD-4 Software (Enraf-Nonius, 1989); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1990).
C14H15N | F(000) = 424 |
Mr = 197.27 | Dx = 1.156 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 15 reflections |
a = 12.056 (2) Å | θ = 3.2–19.7° |
b = 7.545 (1) Å | µ = 0.07 mm−1 |
c = 12.62 (2) Å | T = 293 K |
β = 99.04 (4)° | Plate, yellow |
V = 1133.7 (18) Å3 | 0.20 × 0.15 × 0.06 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | 774 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.053 |
Graphite monochromator | θmax = 26.3°, θmin = 2.2° |
θ/2θ scans | h = −15→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.893, Tmax = 0.935 | l = 0→15 |
2404 measured reflections | 3 standard reflections every 120 min |
2299 independent reflections | intensity decay: none |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3 |
2299 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2419 (2) | 0.5444 (4) | −0.1835 (2) | 0.0521 (11) | |
C2 | 0.3098 (3) | 0.5709 (5) | −0.0869 (3) | 0.0477 (12) | |
C3 | 0.4101 (3) | 0.6283 (5) | −0.1127 (3) | 0.0580 (16) | |
C4 | 0.4028 (3) | 0.6355 (5) | −0.2231 (3) | 0.0568 (16) | |
C5 | 0.2969 (3) | 0.5822 (5) | −0.2678 (3) | 0.0497 (12) | |
C6 | 0.2417 (3) | 0.5665 (6) | −0.3794 (3) | 0.0708 (17) | |
C7 | 0.2739 (3) | 0.5461 (5) | 0.0137 (3) | 0.0512 (14) | |
C8 | 0.1761 (3) | 0.4801 (5) | 0.0323 (3) | 0.0524 (14) | |
C9 | 0.1405 (3) | 0.4691 (5) | 0.1386 (3) | 0.0443 (12) | |
C10 | 0.1794 (3) | 0.5916 (5) | 0.2175 (3) | 0.0553 (14) | |
C11 | 0.1493 (3) | 0.5839 (6) | 0.3177 (3) | 0.0636 (17) | |
C12 | 0.0789 (3) | 0.4530 (6) | 0.3400 (3) | 0.0622 (16) | |
C13 | 0.0372 (3) | 0.3307 (5) | 0.2624 (3) | 0.0548 (16) | |
C14 | 0.0676 (3) | 0.3364 (5) | 0.1624 (3) | 0.0489 (12) | |
C15 | 0.0255 (3) | 0.1941 (5) | 0.0833 (3) | 0.0721 (17) | |
H1 | 0.17350 | 0.50848 | −0.19026 | 0.0627* | |
H3 | 0.47321 | 0.65795 | −0.06354 | 0.0695* | |
H4 | 0.45976 | 0.67025 | −0.26047 | 0.0680* | |
H6A | 0.18691 | 0.65900 | −0.39510 | 0.1064* | |
H6B | 0.29681 | 0.57703 | −0.42634 | 0.1064* | |
H6C | 0.20534 | 0.45331 | −0.38993 | 0.1064* | |
H7 | 0.32437 | 0.57965 | 0.07377 | 0.0615* | |
H8 | 0.12662 | 0.43796 | −0.02625 | 0.0625* | |
H10 | 0.22718 | 0.68140 | 0.20207 | 0.0665* | |
H11 | 0.17663 | 0.66698 | 0.36975 | 0.0765* | |
H12 | 0.05872 | 0.44581 | 0.40797 | 0.0747* | |
H13 | −0.01206 | 0.24339 | 0.27836 | 0.0656* | |
H15A | −0.02876 | 0.12253 | 0.11165 | 0.1079* | |
H15B | −0.00893 | 0.24750 | 0.01716 | 0.1079* | |
H15C | 0.08724 | 0.12120 | 0.07029 | 0.1079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0464 (16) | 0.055 (2) | 0.054 (2) | −0.0079 (16) | 0.0053 (16) | 0.0105 (17) |
C2 | 0.043 (2) | 0.044 (2) | 0.055 (2) | −0.0010 (18) | 0.0041 (18) | 0.0012 (19) |
C3 | 0.045 (2) | 0.057 (3) | 0.071 (3) | −0.001 (2) | 0.0060 (19) | −0.009 (2) |
C4 | 0.052 (2) | 0.059 (3) | 0.062 (3) | −0.004 (2) | 0.0170 (19) | 0.001 (2) |
C5 | 0.054 (2) | 0.041 (2) | 0.055 (2) | 0.0000 (19) | 0.0112 (19) | 0.0021 (19) |
C6 | 0.074 (3) | 0.079 (3) | 0.060 (3) | −0.009 (2) | 0.012 (2) | 0.007 (2) |
C7 | 0.052 (2) | 0.048 (3) | 0.052 (2) | 0.000 (2) | 0.0030 (18) | 0.0011 (19) |
C8 | 0.050 (2) | 0.054 (3) | 0.051 (2) | −0.0052 (19) | 0.0008 (18) | −0.0021 (19) |
C9 | 0.042 (2) | 0.044 (2) | 0.045 (2) | 0.0023 (19) | 0.0012 (17) | −0.0017 (18) |
C10 | 0.050 (2) | 0.053 (3) | 0.062 (2) | −0.007 (2) | 0.0064 (19) | −0.007 (2) |
C11 | 0.060 (3) | 0.072 (3) | 0.058 (3) | −0.004 (2) | 0.007 (2) | −0.011 (2) |
C12 | 0.057 (2) | 0.077 (3) | 0.055 (3) | 0.010 (2) | 0.016 (2) | 0.004 (2) |
C13 | 0.046 (2) | 0.058 (3) | 0.060 (3) | 0.002 (2) | 0.0070 (19) | 0.003 (2) |
C14 | 0.045 (2) | 0.044 (2) | 0.057 (2) | −0.0009 (18) | 0.0061 (18) | −0.0039 (19) |
C15 | 0.070 (3) | 0.064 (3) | 0.084 (3) | −0.014 (2) | 0.017 (2) | −0.009 (2) |
N1—C2 | 1.372 (5) | C14—C15 | 1.499 (6) |
N1—C5 | 1.368 (5) | C3—H3 | 0.9303 |
N1—H1 | 0.8606 | C4—H4 | 0.9298 |
C2—C7 | 1.417 (6) | C6—H6A | 0.9600 |
C2—C3 | 1.371 (6) | C6—H6B | 0.9604 |
C3—C4 | 1.383 (6) | C6—H6C | 0.9596 |
C4—C5 | 1.372 (6) | C7—H7 | 0.9295 |
C5—C6 | 1.465 (6) | C8—H8 | 0.9297 |
C7—C8 | 1.334 (6) | C10—H10 | 0.9295 |
C8—C9 | 1.474 (6) | C11—H11 | 0.9300 |
C9—C14 | 1.396 (6) | C12—H12 | 0.9292 |
C9—C10 | 1.385 (6) | C13—H13 | 0.9299 |
C10—C11 | 1.371 (6) | C15—H15A | 0.9597 |
C11—C12 | 1.360 (6) | C15—H15B | 0.9604 |
C12—C13 | 1.382 (6) | C15—H15C | 0.9602 |
C13—C14 | 1.369 (6) | ||
N1···H8 | 2.7176 | H6C···C2vii | 2.9029 |
C2···H6Ci | 2.9029 | H6C···C3vii | 2.8224 |
C3···H6Ci | 2.8224 | H7···C10 | 2.7109 |
C4···H13ii | 3.0365 | H7···H10 | 2.2760 |
C4···H15Aii | 3.0595 | H7···C13viii | 3.0925 |
C7···H10 | 2.7261 | H8···N1 | 2.7176 |
C8···H1 | 2.8121 | H8···C15 | 2.7042 |
C8···H15B | 2.8211 | H8···H1 | 2.2922 |
C8···H15C | 2.9785 | H8···H15B | 2.3059 |
C8···H11iii | 3.0939 | H10···C7 | 2.7261 |
C8···H15Biv | 2.8775 | H10···H7 | 2.2760 |
C10···H7 | 2.7109 | H10···C13viii | 3.0231 |
C11···H4v | 2.9879 | H10···C14viii | 3.0141 |
C13···H7iii | 3.0925 | H11···C8viii | 3.0939 |
C13···H10iii | 3.0231 | H13···H15A | 2.2727 |
C13···H1iv | 2.8332 | H13···C4ix | 3.0365 |
C14···H10iii | 3.0141 | H15A···H13 | 2.2727 |
C15···H8 | 2.7042 | H15A···C4ix | 3.0595 |
H1···C8 | 2.8121 | H15A···H6Bix | 2.5695 |
H1···H8 | 2.2922 | H15B···C8 | 2.8211 |
H1···C13iv | 2.8332 | H15B···H8 | 2.3059 |
H4···C11vi | 2.9879 | H15B···C8iv | 2.8775 |
H6B···H15Ci | 2.4826 | H15C···C8 | 2.9785 |
H6B···H15Aii | 2.5695 | H15C···H6Bvii | 2.4826 |
C2—N1—C5 | 111.5 (3) | C5—C4—H4 | 125.99 |
C5—N1—H1 | 124.22 | C5—C6—H6A | 109.49 |
C2—N1—H1 | 124.24 | C5—C6—H6B | 109.42 |
N1—C2—C7 | 123.6 (3) | C5—C6—H6C | 109.50 |
N1—C2—C3 | 105.1 (3) | H6A—C6—H6B | 109.44 |
C3—C2—C7 | 131.3 (4) | H6A—C6—H6C | 109.51 |
C2—C3—C4 | 109.4 (3) | H6B—C6—H6C | 109.48 |
C3—C4—C5 | 108.1 (3) | C2—C7—H7 | 116.23 |
C4—C5—C6 | 132.2 (4) | C8—C7—H7 | 116.20 |
N1—C5—C6 | 121.9 (3) | C7—C8—H8 | 117.53 |
N1—C5—C4 | 105.9 (3) | C9—C8—H8 | 117.51 |
C2—C7—C8 | 127.6 (4) | C9—C10—H10 | 119.12 |
C7—C8—C9 | 125.0 (3) | C11—C10—H10 | 119.13 |
C10—C9—C14 | 118.5 (3) | C10—C11—H11 | 120.49 |
C8—C9—C10 | 120.2 (3) | C12—C11—H11 | 120.44 |
C8—C9—C14 | 121.3 (3) | C11—C12—H12 | 119.72 |
C9—C10—C11 | 121.7 (4) | C13—C12—H12 | 119.77 |
C10—C11—C12 | 119.1 (4) | C12—C13—H13 | 119.56 |
C11—C12—C13 | 120.5 (4) | C14—C13—H13 | 119.64 |
C12—C13—C14 | 120.8 (4) | C14—C15—H15A | 109.51 |
C13—C14—C15 | 118.7 (3) | C14—C15—H15B | 109.46 |
C9—C14—C13 | 119.3 (3) | C14—C15—H15C | 109.49 |
C9—C14—C15 | 122.0 (3) | H15A—C15—H15B | 109.46 |
C2—C3—H3 | 125.24 | H15A—C15—H15C | 109.48 |
C4—C3—H3 | 125.32 | H15B—C15—H15C | 109.42 |
C3—C4—H4 | 125.93 | ||
C5—N1—C2—C3 | 0.4 (4) | C7—C8—C9—C10 | 29.1 (6) |
C5—N1—C2—C7 | 178.4 (4) | C14—C9—C10—C11 | 0.9 (6) |
C2—N1—C5—C4 | −0.4 (4) | C8—C9—C14—C13 | 179.7 (3) |
C2—N1—C5—C6 | −179.2 (4) | C8—C9—C14—C15 | 2.6 (6) |
N1—C2—C3—C4 | −0.2 (4) | C8—C9—C10—C11 | −179.1 (4) |
C7—C2—C3—C4 | −178.1 (4) | C10—C9—C14—C13 | −0.3 (5) |
C3—C2—C7—C8 | −176.0 (4) | C10—C9—C14—C15 | −177.3 (3) |
N1—C2—C7—C8 | 6.5 (6) | C9—C10—C11—C12 | −0.3 (6) |
C2—C3—C4—C5 | 0.0 (5) | C10—C11—C12—C13 | −0.8 (6) |
C3—C4—C5—N1 | 0.2 (4) | C11—C12—C13—C14 | 1.4 (6) |
C3—C4—C5—C6 | 178.8 (4) | C12—C13—C14—C9 | −0.8 (6) |
C2—C7—C8—C9 | −175.5 (4) | C12—C13—C14—C15 | 176.3 (4) |
C7—C8—C9—C14 | −150.9 (4) |
Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+1, −z; (v) x−1/2, −y+3/2, z+1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) −x+1/2, y−1/2, −z−1/2; (viii) −x+1/2, y+1/2, −z+1/2; (ix) x−1/2, −y+1/2, z+1/2. |
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