

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809025963/ng2608sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809025963/ng2608Isup2.hkl |
CCDC reference: 744388
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.115
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 1324 Count of symmetry unique reflns 1325 Completeness (_total/calc) 99.92% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1,3-Propane diamine (1 g, 0.013 mmol) was mixed with 1-(2-pyridinyl)-1-ethanone (1.635 g, 0.013 mmol) in 30 ml e thanol. The mixture was stirred under reflux for 5 h. The solution was concentrated under reduced pressure and the product was precipitated by addition of 30 ml of cool distilled water. Product was filtered off and washed three times with 15 ml of distilled water then dried under vacuum. Crude product was recrystallized from ethanol and allowed to stand at room temperature. Crystals were collected after 2 weeks.
Hydrogen atoms were refined isotropically and were constrained to the ideal geometry using an appropriate riding model with Uiso(H) fixed at 1.2 times Ueq of the pivot atom. The —NH hydrogen atoms was located from difference Fourier map and refined isotropically without constraints. 949 Friedel-pair reflections were merged for a weak anomalous scatterer structure.
Data collection: CrystalClear (Rigaku/MSC, 2007); cell refinement: CrystalClear (Rigaku/MSC, 2007); data reduction: CrystalClear (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006) and PLUTO (Motherwell et al., 1999); software used to prepare material for publication: publCIF (Westrip, 2009).
C10H15N3 | F(000) = 384 |
Mr = 177.25 | Dx = 1.188 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7168 reflections |
a = 8.4070 (17) Å | θ = 3.0–27.5° |
b = 10.371 (2) Å | µ = 0.07 mm−1 |
c = 11.363 (2) Å | T = 294 K |
V = 990.7 (3) Å3 | Plate, yellow |
Z = 4 | 0.35 × 0.15 × 0.15 mm |
Rigaku R-AXIS RAPID diffractometer | 1324 independent reflections |
Radiation source: fine-focus sealed tube | 1206 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007) | h = −10→10 |
Tmin = 0.97, Tmax = 0.99 | k = −13→12 |
8017 measured reflections | l = −13→14 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0907P)2 + 0.0352P] where P = (Fo2 + 2Fc2)/3 |
1324 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C10H15N3 | V = 990.7 (3) Å3 |
Mr = 177.25 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.4070 (17) Å | µ = 0.07 mm−1 |
b = 10.371 (2) Å | T = 294 K |
c = 11.363 (2) Å | 0.35 × 0.15 × 0.15 mm |
Rigaku R-AXIS RAPID diffractometer | 1324 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007) | 1206 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.99 | Rint = 0.022 |
8017 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.20 e Å−3 |
1324 reflections | Δρmin = −0.34 e Å−3 |
128 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20810 (17) | 0.34068 (14) | 0.21846 (15) | 0.0473 (4) | |
C1 | 0.3442 (2) | 0.27459 (18) | 0.2066 (2) | 0.0562 (5) | |
H1 | 0.3416 | 0.1859 | 0.2183 | 0.067* | |
N2 | 0.05820 (18) | 0.66511 (13) | 0.16234 (14) | 0.0475 (3) | |
H2A | −0.026 (3) | 0.711 (2) | 0.187 (2) | 0.063 (6)* | |
C2 | 0.4872 (2) | 0.3304 (2) | 0.17791 (18) | 0.0553 (5) | |
H2 | 0.5789 | 0.2809 | 0.1707 | 0.066* | |
N3 | −0.08570 (15) | 0.46514 (15) | 0.18351 (14) | 0.0436 (3) | |
H3A | −0.087 (3) | 0.391 (2) | 0.221 (2) | 0.063 (6)* | |
C3 | 0.49114 (19) | 0.4615 (2) | 0.16021 (17) | 0.0518 (4) | |
H3 | 0.5861 | 0.5025 | 0.1410 | 0.062* | |
C4 | 0.35197 (19) | 0.53176 (17) | 0.17129 (16) | 0.0445 (4) | |
H4 | 0.3523 | 0.6205 | 0.1599 | 0.053* | |
C5 | 0.21182 (17) | 0.46810 (14) | 0.19969 (13) | 0.0364 (3) | |
C6 | 0.05402 (18) | 0.53948 (14) | 0.22108 (14) | 0.0385 (3) | |
C7 | 0.0394 (3) | 0.5618 (2) | 0.35388 (16) | 0.0574 (5) | |
H7A | 0.1299 | 0.6097 | 0.3812 | 0.086* | |
H7B | 0.0352 | 0.4802 | 0.3936 | 0.086* | |
H7C | −0.0560 | 0.6095 | 0.3701 | 0.086* | |
C8 | −0.0901 (2) | 0.44394 (19) | 0.05613 (18) | 0.0536 (4) | |
H8A | −0.1817 | 0.3918 | 0.0356 | 0.064* | |
H8B | 0.0051 | 0.3987 | 0.0311 | 0.064* | |
C9 | −0.1001 (3) | 0.5740 (2) | −0.00463 (18) | 0.0630 (5) | |
H9A | −0.0978 | 0.5624 | −0.0893 | 0.076* | |
H9B | −0.1990 | 0.6164 | 0.0161 | 0.076* | |
C10 | 0.0403 (2) | 0.6562 (2) | 0.03398 (18) | 0.0574 (5) | |
H10A | 0.1370 | 0.6202 | 0.0009 | 0.069* | |
H10B | 0.0274 | 0.7424 | 0.0022 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0406 (7) | 0.0382 (6) | 0.0631 (9) | 0.0007 (6) | 0.0038 (7) | 0.0057 (6) |
C1 | 0.0532 (10) | 0.0419 (8) | 0.0737 (12) | 0.0105 (8) | 0.0012 (9) | 0.0040 (9) |
N2 | 0.0480 (7) | 0.0342 (6) | 0.0602 (8) | 0.0046 (6) | 0.0084 (7) | 0.0023 (6) |
C2 | 0.0406 (8) | 0.0658 (11) | 0.0594 (10) | 0.0145 (8) | 0.0010 (7) | −0.0043 (9) |
N3 | 0.0321 (6) | 0.0439 (7) | 0.0549 (8) | −0.0012 (5) | 0.0053 (5) | 0.0062 (7) |
C3 | 0.0340 (7) | 0.0649 (10) | 0.0564 (9) | −0.0048 (7) | 0.0033 (7) | −0.0035 (9) |
C4 | 0.0388 (7) | 0.0425 (7) | 0.0522 (9) | −0.0059 (6) | 0.0040 (6) | −0.0022 (7) |
C5 | 0.0340 (7) | 0.0353 (7) | 0.0400 (7) | −0.0006 (6) | 0.0011 (6) | −0.0017 (6) |
C6 | 0.0371 (7) | 0.0359 (7) | 0.0427 (7) | 0.0006 (6) | 0.0067 (6) | 0.0007 (6) |
C7 | 0.0614 (11) | 0.0643 (11) | 0.0466 (9) | 0.0089 (9) | 0.0088 (8) | −0.0057 (8) |
C8 | 0.0415 (8) | 0.0590 (10) | 0.0603 (10) | −0.0022 (8) | −0.0019 (7) | −0.0084 (8) |
C9 | 0.0568 (11) | 0.0812 (13) | 0.0509 (10) | 0.0073 (10) | −0.0036 (8) | 0.0088 (10) |
C10 | 0.0591 (10) | 0.0551 (9) | 0.0579 (10) | 0.0062 (9) | 0.0097 (9) | 0.0181 (9) |
N1—C1 | 1.340 (2) | C4—H4 | 0.9300 |
N1—C5 | 1.339 (2) | C5—C6 | 1.539 (2) |
C1—C2 | 1.374 (3) | C6—C7 | 1.532 (2) |
C1—H1 | 0.9300 | C7—H7A | 0.9600 |
N2—C10 | 1.469 (3) | C7—H7B | 0.9600 |
N2—C6 | 1.464 (2) | C7—H7C | 0.9600 |
N2—H2A | 0.89 (3) | C8—C9 | 1.517 (3) |
C2—C3 | 1.375 (3) | C8—H8A | 0.9700 |
C2—H2 | 0.9300 | C8—H8B | 0.9700 |
N3—C6 | 1.468 (2) | C9—C10 | 1.521 (3) |
N3—C8 | 1.464 (3) | C9—H9A | 0.9700 |
N3—H3A | 0.88 (3) | C9—H9B | 0.9700 |
C3—C4 | 1.384 (2) | C10—H10A | 0.9700 |
C3—H3 | 0.9300 | C10—H10B | 0.9700 |
C4—C5 | 1.389 (2) | ||
C1—N1—C5 | 117.95 (14) | N2—C6—C5 | 109.60 (12) |
N1—C1—C2 | 123.75 (16) | C7—C6—C5 | 107.30 (14) |
N1—C1—H1 | 118.1 | C6—C7—H7A | 109.5 |
C2—C1—H1 | 118.1 | C6—C7—H7B | 109.5 |
C10—N2—C6 | 113.21 (14) | H7A—C7—H7B | 109.5 |
C10—N2—H2A | 105.3 (17) | C6—C7—H7C | 109.5 |
C6—N2—H2A | 108.1 (16) | H7A—C7—H7C | 109.5 |
C3—C2—C1 | 118.18 (16) | H7B—C7—H7C | 109.5 |
C3—C2—H2 | 120.9 | N3—C8—C9 | 108.52 (16) |
C1—C2—H2 | 120.9 | N3—C8—H8A | 110.0 |
C6—N3—C8 | 112.72 (13) | C9—C8—H8A | 110.0 |
C6—N3—H3A | 109.1 (16) | N3—C8—H8B | 110.0 |
C8—N3—H3A | 110.1 (16) | C9—C8—H8B | 110.0 |
C2—C3—C4 | 119.15 (16) | H8A—C8—H8B | 108.4 |
C2—C3—H3 | 120.4 | C10—C9—C8 | 108.91 (16) |
C4—C3—H3 | 120.4 | C10—C9—H9A | 109.9 |
C5—C4—C3 | 119.22 (16) | C8—C9—H9A | 109.9 |
C5—C4—H4 | 120.4 | C10—C9—H9B | 109.9 |
C3—C4—H4 | 120.4 | C8—C9—H9B | 109.9 |
N1—C5—C4 | 121.74 (15) | H9A—C9—H9B | 108.3 |
N1—C5—C6 | 115.44 (13) | N2—C10—C9 | 113.65 (16) |
C4—C5—C6 | 122.65 (13) | N2—C10—H10A | 108.8 |
N3—C6—N2 | 110.72 (13) | C9—C10—H10A | 108.8 |
N3—C6—C7 | 107.56 (13) | N2—C10—H10B | 108.8 |
N2—C6—C7 | 108.46 (14) | C9—C10—H10B | 108.8 |
N3—C6—C5 | 113.03 (12) | H10A—C10—H10B | 107.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.89 (3) | 2.31 (3) | 3.188 (2) | 168 (2) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H15N3 |
Mr | 177.25 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 8.4070 (17), 10.371 (2), 11.363 (2) |
V (Å3) | 990.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.35 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2007) |
Tmin, Tmax | 0.97, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8017, 1324, 1206 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.115, 1.01 |
No. of reflections | 1324 |
No. of parameters | 128 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.34 |
Computer programs: CrystalClear (Rigaku/MSC, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006) and PLUTO (Motherwell et al., 1999), publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.89 (3) | 2.31 (3) | 3.188 (2) | 168 (2) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
The title compound was known as precursor for syntheses of umsymmetrical tetradentate Schiff base ligands that form bistable Fe(II) spin crossover materials (Bréfuel et al. 2007).
The molecular packing of the title compound is supported by N— H···N intermolecular hydrogen bondings at H···A distance of 2.31 (3) and D— H···A angle of 168 (2)° and calculated with Pluto (Motherwell et al., 1999), see Figure 2.