Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023888/dn6163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023888/dn6163Isup2.hkl |
CCDC reference: 255477
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.088
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT374_ALERT_2_A Long N - N Bond N11 - N12 ... 1.51 Ang.
Alert level C PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.64
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 and NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 1995); software used to prepare material for publication: SHELXL97.
C6H12N2 | F(000) = 248.0 |
Mr = 112.18 | Dx = 1.120 Mg m−3 |
Monoclinic, P21/c | Melting point: 107 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54178 Å |
a = 10.373 (3) Å | Cell parameters from 25 reflections |
b = 8.037 (3) Å | θ = 20.0–25.0° |
c = 8.077 (3) Å | µ = 0.54 mm−1 |
β = 98.86 (3)° | T = 293 K |
V = 665.3 (4) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.36 × 0.23 mm |
Enraf–Nonius CAD-4 diffractometer | 872 reflections with I > 2σ(I) |
Radiation source: normal-focus xray tube | Rint = 0.070 |
Graphite monochromator | θmax = 69.9°, θmin = 4.3° |
ω scan | h = −12→12 |
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989) | k = −9→9 |
Tmin = 0.819, Tmax = 0.898 | l = −9→9 |
19833 measured reflections | 5 standard reflections every 60 min |
1253 independent reflections | intensity decay: 2.1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | All H-atom parameters refined |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0551P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max = 0.001 |
1253 reflections | Δρmax = 0.12 e Å−3 |
130 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.072 (4) |
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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor_obs 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 | Occ. (<1) | |
N11 | 0.53841 (11) | 0.94402 (18) | 0.68680 (19) | 0.0725 (4) | |
H11A | 0.519 (4) | 0.836 (6) | 0.706 (5) | 0.141 (15)* | 0.50 |
H11B | 0.521 (4) | 0.967 (5) | 0.580 (4) | 0.114 (14)* | 0.50 |
N12 | 0.52104 (10) | 1.06808 (16) | 0.82174 (16) | 0.0682 (4) | |
H12A | 0.483 (3) | 1.157 (4) | 0.756 (4) | 0.080 (8)* | 0.50 |
H12B | 0.508 (3) | 1.015 (4) | 0.923 (3) | 0.075 (8)* | 0.50 |
C1 | 0.64843 (11) | 1.02759 (14) | 0.78250 (13) | 0.0541 (3) | |
C2 | 0.73685 (13) | 0.92490 (19) | 0.90762 (17) | 0.0681 (4) | |
H2A | 0.6801 (15) | 0.8388 (19) | 0.9542 (17) | 0.092 (4)* | |
H2B | 0.7770 (15) | 0.9972 (18) | 1.0029 (17) | 0.090 (5)* | |
C3 | 0.84431 (14) | 0.8457 (2) | 0.8262 (2) | 0.0762 (4) | |
H3A | 0.9075 (15) | 0.7837 (19) | 0.9161 (19) | 0.097 (5)* | |
H3B | 0.8021 (15) | 0.7600 (19) | 0.741 (2) | 0.094 (5)* | |
C4 | 0.91702 (13) | 0.9740 (2) | 0.7386 (2) | 0.0822 (5) | |
H4A | 0.9852 (15) | 0.9166 (19) | 0.6830 (16) | 0.093 (5)* | |
H4B | 0.9613 (15) | 1.0492 (19) | 0.8250 (18) | 0.094 (5)* | |
C5 | 0.82412 (13) | 1.0722 (2) | 0.61154 (18) | 0.0750 (4) | |
H5A | 0.7833 (14) | 0.9945 (17) | 0.5185 (16) | 0.081 (4)* | |
H5B | 0.8722 (14) | 1.1564 (19) | 0.5549 (18) | 0.096 (5)* | |
C6 | 0.71696 (12) | 1.15454 (17) | 0.69129 (17) | 0.0633 (4) | |
H6A | 0.7559 (15) | 1.2415 (18) | 0.7779 (18) | 0.088 (4)* | |
H6B | 0.6488 (13) | 1.2098 (15) | 0.6059 (17) | 0.076 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0553 (6) | 0.0727 (8) | 0.0895 (9) | −0.0084 (6) | 0.0117 (6) | −0.0100 (7) |
N12 | 0.0582 (6) | 0.0736 (8) | 0.0764 (7) | 0.0117 (5) | 0.0220 (5) | 0.0074 (6) |
C1 | 0.0480 (6) | 0.0558 (6) | 0.0590 (6) | 0.0019 (5) | 0.0104 (5) | 0.0016 (5) |
C2 | 0.0623 (7) | 0.0761 (9) | 0.0662 (8) | 0.0130 (7) | 0.0112 (6) | 0.0120 (7) |
C3 | 0.0615 (8) | 0.0867 (10) | 0.0797 (9) | 0.0204 (7) | 0.0080 (7) | 0.0061 (8) |
C4 | 0.0513 (7) | 0.1095 (12) | 0.0865 (10) | 0.0066 (8) | 0.0131 (7) | 0.0023 (9) |
C5 | 0.0569 (7) | 0.0954 (10) | 0.0752 (9) | −0.0054 (7) | 0.0181 (6) | 0.0094 (8) |
C6 | 0.0567 (7) | 0.0635 (8) | 0.0695 (8) | −0.0065 (6) | 0.0090 (6) | 0.0059 (7) |
N11—C1 | 1.4420 (16) | C3—C4 | 1.515 (2) |
N11—N12 | 1.5083 (17) | C3—H3A | 1.029 (16) |
N11—H11A | 0.91 (5) | C3—H3B | 1.024 (16) |
N11—H11B | 0.87 (3) | C4—C5 | 1.517 (2) |
N12—C1 | 1.4427 (14) | C4—H4A | 1.006 (15) |
N12—H12A | 0.94 (3) | C4—H4B | 0.983 (15) |
N12—H12B | 0.95 (2) | C5—C6 | 1.5195 (18) |
C1—C6 | 1.5002 (16) | C5—H5A | 1.018 (13) |
C1—C2 | 1.5027 (17) | C5—H5B | 0.993 (16) |
C2—C3 | 1.5186 (18) | C6—H6A | 1.027 (15) |
C2—H2A | 1.017 (15) | C6—H6B | 1.011 (13) |
C2—H2B | 1.002 (14) | ||
C1—N11—N12 | 58.50 (7) | C4—C3—C2 | 111.62 (13) |
C1—N11—H11A | 122 (3) | C4—C3—H3A | 110.5 (9) |
N12—N11—H11A | 117 (2) | C2—C3—H3A | 109.1 (8) |
C1—N11—H11B | 117 (3) | C4—C3—H3B | 109.6 (9) |
N12—N11—H11B | 123 (3) | C2—C3—H3B | 107.9 (9) |
H11A—N11—H11B | 111 (4) | H3A—C3—H3B | 108.0 (12) |
C1—N12—N11 | 58.45 (7) | C3—C4—C5 | 111.09 (12) |
C1—N12—H12A | 111.6 (17) | C3—C4—H4A | 109.3 (8) |
N11—N12—H12A | 100.5 (18) | C5—C4—H4A | 110.7 (8) |
C1—N12—H12B | 110.4 (17) | C3—C4—H4B | 107.4 (9) |
N11—N12—H12B | 112.2 (17) | C5—C4—H4B | 109.8 (9) |
H12A—N12—H12B | 136 (2) | H4A—C4—H4B | 108.3 (13) |
N11—C1—N12 | 63.05 (8) | C4—C5—C6 | 111.71 (11) |
N11—C1—C6 | 116.70 (11) | C4—C5—H5A | 109.2 (8) |
N12—C1—C6 | 118.28 (11) | C6—C5—H5A | 109.4 (8) |
N11—C1—C2 | 117.09 (12) | C4—C5—H5B | 110.7 (8) |
N12—C1—C2 | 117.45 (10) | C6—C5—H5B | 110.6 (8) |
C6—C1—C2 | 114.68 (11) | H5A—C5—H5B | 105.0 (11) |
C1—C2—C3 | 110.58 (11) | C1—C6—C5 | 110.18 (11) |
C1—C2—H2A | 107.1 (8) | C1—C6—H6A | 107.2 (8) |
C3—C2—H2A | 112.3 (8) | C5—C6—H6A | 110.4 (8) |
C1—C2—H2B | 109.7 (8) | C1—C6—H6B | 107.4 (7) |
C3—C2—H2B | 109.2 (9) | C5—C6—H6B | 112.5 (7) |
H2A—C2—H2B | 107.8 (11) | H6A—C6—H6B | 109.0 (10) |
N12—N11—C1—C6 | −109.83 (13) | C1—C2—C3—C4 | 53.23 (18) |
N12—N11—C1—C2 | 108.71 (12) | C2—C3—C4—C5 | −55.61 (18) |
N11—N12—C1—C6 | 107.39 (13) | C3—C4—C5—C6 | 56.07 (19) |
N11—N12—C1—C2 | −108.15 (14) | N11—C1—C6—C5 | −88.99 (14) |
N11—C1—C2—C3 | 89.02 (15) | N12—C1—C6—C5 | −161.20 (11) |
N12—C1—C2—C3 | 161.08 (12) | C2—C1—C6—C5 | 53.39 (14) |
C6—C1—C2—C3 | −53.21 (16) | C4—C5—C6—C1 | −53.88 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···N12i | 0.91 | 2.20 | 3.082 (2) | 164 |
N11—H11B···N11ii | 0.87 | 2.26 | 3.132 (3) | 173 |
N12—H12A···N11iii | 0.94 | 2.37 | 3.082 (2) | 132 |
N12—H12B···N12iv | 0.95 | 2.23 | 3.173 (3) | 171 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+2. |
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