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The crystal structure of the title compound, C14H17N3O, at 180 K contains intermolecular hydrogen bonds between the hydroxyl group and the N atom of one pyridyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013534/dn6145sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013534/dn6145Isup2.hkl
Contains datablock I

CCDC reference: 245278

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.089
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



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 28.69 From the CIF: _reflns_number_total 1958 Count of symmetry unique reflns 1971 Completeness (_total/calc) 99.34% 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 0 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 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker-Nonius, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

bis(2-{pyridyl-2-yl}ethyl)hydroxylamine top
Crystal data top
C14H17N3OF(000) = 520
Mr = 243.31Dx = 1.230 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 3638 reflections
a = 5.8501 (4) Åθ = 2.7–28.4°
b = 14.7210 (9) ŵ = 0.08 mm1
c = 15.2578 (10) ÅT = 180 K
V = 1313.99 (15) Å3Block, colourless
Z = 40.40 × 0.30 × 0.10 mm
Data collection top
Bruker-Nonius X8APEX-II CCD
diffractometer
1958 independent reflections
Radiation source: fine-focus sealed tube1681 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
thin–slice ω and φ scansθmax = 28.7°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS;Sheldrick, 2003)
h = 77
Tmin = 0.885, Tmax = 0.992k = 1719
9849 measured reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.1214P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1958 reflectionsΔρmax = 0.23 e Å3
167 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: Absolute structure unknown. 1286 Friedel opposites merged for final refinement.
Primary atom site location: structure-invariant direct methods
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.7504 (0.0042) x + 0.7200 (0.0127) y + 11.6862 (0.0092) z = 8.5344 (0.0098)

* 0.0060 (0.0013) N2 * -0.0045 (0.0013) C3 * -0.0020 (0.0016) C4 * 0.0070 (0.0017) C5 * -0.0056 (0.0015) C6 * -0.0009 (0.0015) C7

Rms deviation of fitted atoms = 0.0049

2.2110 (0.0036) x + 13.5034 (0.0040) y + 1.9143 (0.0104) z = 6.5086 (0.0053)

Angle to previous plane (with approximate e.s.d.) = 67.47 (0.07)

* -0.0020 (0.0010) N3 * -0.0016 (0.0011) C10 * 0.0033 (0.0011) C11 * -0.0015 (0.0012) C12 * -0.0019 (0.0012) C13 * 0.0038 (0.0012) C14

Rms deviation of fitted atoms = 0.0025

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
xyzUiso*/Ueq
O10.7795 (2)0.44983 (8)0.36003 (8)0.0344 (3)
H10.853 (4)0.4370 (16)0.4101 (16)0.064 (7)*
N10.5902 (2)0.50545 (8)0.38993 (8)0.0273 (3)
N21.0828 (3)0.73507 (10)0.33801 (10)0.0416 (4)
N30.0778 (2)0.39875 (9)0.49638 (9)0.0323 (3)
C10.6456 (3)0.59867 (11)0.36448 (10)0.0304 (3)
H1A0.50720.63700.36950.036*
H1B0.69620.59960.30260.036*
C20.8336 (3)0.63726 (11)0.42245 (11)0.0330 (3)
H2A0.77820.64020.48370.040*
H2B0.96720.59600.42100.040*
C30.9070 (3)0.73032 (11)0.39383 (10)0.0295 (3)
C40.7995 (4)0.80765 (13)0.42379 (14)0.0505 (5)
H4A0.67520.80280.46360.061*
C50.8719 (5)0.89218 (13)0.39612 (14)0.0560 (6)
H5A0.80010.94580.41710.067*
C61.0480 (4)0.89715 (12)0.33820 (12)0.0437 (5)
H6A1.10030.95410.31690.052*
C71.1478 (4)0.81789 (13)0.31149 (12)0.0478 (5)
H7A1.27160.82180.27140.057*
C80.3920 (3)0.47228 (11)0.34149 (10)0.0311 (3)
H8A0.42720.47230.27800.037*
H8B0.26140.51380.35130.037*
C90.3248 (3)0.37632 (11)0.36984 (10)0.0316 (3)
H9A0.18510.35780.33790.038*
H9B0.44860.33370.35360.038*
C100.2814 (3)0.36960 (10)0.46696 (10)0.0277 (3)
C110.4456 (3)0.33506 (11)0.52349 (11)0.0323 (3)
H11A0.58890.31520.50130.039*
C120.3996 (3)0.32966 (11)0.61220 (11)0.0374 (4)
H12A0.51010.30580.65160.045*
C130.1908 (3)0.35953 (12)0.64252 (11)0.0388 (4)
H13A0.15400.35670.70310.047*
C140.0371 (3)0.39360 (12)0.58269 (12)0.0378 (4)
H14A0.10620.41470.60380.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (6)0.0386 (6)0.0365 (6)0.0095 (5)0.0007 (5)0.0023 (5)
N10.0236 (6)0.0283 (6)0.0301 (6)0.0031 (5)0.0008 (5)0.0010 (5)
N20.0465 (9)0.0373 (7)0.0410 (7)0.0013 (7)0.0150 (7)0.0011 (6)
N30.0250 (7)0.0305 (7)0.0415 (7)0.0014 (6)0.0011 (6)0.0014 (6)
C10.0300 (8)0.0301 (7)0.0311 (7)0.0005 (7)0.0019 (7)0.0049 (6)
C20.0335 (8)0.0326 (8)0.0330 (7)0.0018 (7)0.0025 (7)0.0033 (6)
C30.0298 (8)0.0327 (8)0.0260 (7)0.0000 (7)0.0010 (6)0.0009 (6)
C40.0545 (12)0.0408 (9)0.0561 (11)0.0100 (10)0.0253 (10)0.0061 (8)
C50.0783 (16)0.0326 (9)0.0570 (12)0.0129 (11)0.0166 (12)0.0005 (8)
C60.0610 (13)0.0344 (8)0.0357 (8)0.0089 (9)0.0034 (9)0.0047 (7)
C70.0538 (12)0.0469 (10)0.0426 (9)0.0078 (10)0.0170 (9)0.0044 (8)
C80.0280 (8)0.0340 (8)0.0314 (7)0.0000 (7)0.0038 (6)0.0036 (6)
C90.0322 (8)0.0310 (8)0.0318 (7)0.0026 (7)0.0025 (7)0.0013 (6)
C100.0261 (8)0.0224 (7)0.0346 (7)0.0018 (6)0.0018 (6)0.0003 (6)
C110.0270 (8)0.0309 (8)0.0389 (8)0.0038 (7)0.0005 (7)0.0021 (6)
C120.0394 (10)0.0354 (9)0.0374 (8)0.0002 (8)0.0056 (8)0.0058 (7)
C130.0468 (10)0.0351 (8)0.0345 (8)0.0056 (8)0.0048 (8)0.0010 (7)
C140.0306 (9)0.0359 (8)0.0468 (9)0.0002 (7)0.0078 (8)0.0057 (7)
Geometric parameters (Å, º) top
O1—N11.4509 (16)C5—H5A0.950
O1—H10.90 (3)C6—C71.367 (3)
N1—C81.459 (2)C6—H6A0.950
N1—C11.4625 (19)C7—H7A0.950
N2—C31.337 (2)C8—C91.529 (2)
N2—C71.340 (2)C8—H8A0.990
N3—C141.341 (2)C8—H8B0.990
N3—C101.344 (2)C9—C101.507 (2)
C1—C21.522 (2)C9—H9A0.990
C1—H1A0.990C9—H9B0.990
C1—H1B0.990C10—C111.387 (2)
C2—C31.501 (2)C11—C121.382 (2)
C2—H2A0.990C11—H11A0.950
C2—H2B0.990C12—C131.378 (3)
C3—C41.379 (2)C12—H12A0.950
C4—C51.381 (3)C13—C141.376 (3)
C4—H4A0.950C13—H13A0.950
C5—C61.360 (3)C14—H14A0.950
N1—O1—H1102.6 (15)N2—C7—C6124.47 (18)
O1—N1—C8104.98 (11)N2—C7—H7A117.8
O1—N1—C1106.07 (12)C6—C7—H7A117.8
C8—N1—C1110.83 (12)N1—C8—C9111.72 (13)
C3—N2—C7117.26 (15)N1—C8—H8A109.3
C14—N3—C10117.88 (15)C9—C8—H8A109.3
N1—C1—C2110.86 (13)N1—C8—H8B109.3
N1—C1—H1A109.5C9—C8—H8B109.3
C2—C1—H1A109.5H8A—C8—H8B107.9
N1—C1—H1B109.5C10—C9—C8112.48 (13)
C2—C1—H1B109.5C10—C9—H9A109.1
H1A—C1—H1B108.1C8—C9—H9A109.1
C3—C2—C1112.24 (13)C10—C9—H9B109.1
C3—C2—H2A109.2C8—C9—H9B109.1
C1—C2—H2A109.2H9A—C9—H9B107.8
C3—C2—H2B109.2N3—C10—C11121.55 (15)
C1—C2—H2B109.2N3—C10—C9117.19 (14)
H2A—C2—H2B107.9C11—C10—C9121.26 (15)
N2—C3—C4121.26 (15)C12—C11—C10119.67 (16)
N2—C3—C2116.94 (14)C12—C11—H11A120.2
C4—C3—C2121.80 (16)C10—C11—H11A120.2
C3—C4—C5120.19 (18)C13—C12—C11118.88 (17)
C3—C4—H4A119.9C13—C12—H12A120.6
C5—C4—H4A119.9C11—C12—H12A120.6
C6—C5—C4118.67 (18)C14—C13—C12118.22 (16)
C6—C5—H5A120.7C14—C13—H13A120.9
C4—C5—H5A120.7C12—C13—H13A120.9
C5—C6—C7118.12 (17)N3—C14—C13123.79 (17)
C5—C6—H6A120.9N3—C14—H14A118.1
C7—C6—H6A120.9C13—C14—H14A118.1
O1—N1—C1—C273.37 (15)O1—N1—C8—C968.29 (15)
C8—N1—C1—C2173.21 (13)C1—N1—C8—C9177.60 (13)
N1—C1—C2—C3175.70 (13)N1—C8—C9—C1055.69 (18)
C7—N2—C3—C41.0 (3)C14—N3—C10—C110.1 (2)
C7—N2—C3—C2179.34 (17)C14—N3—C10—C9179.69 (14)
C1—C2—C3—N292.35 (19)C8—C9—C10—N379.67 (18)
C1—C2—C3—C487.9 (2)C8—C9—C10—C11100.08 (18)
N2—C3—C4—C50.2 (3)N3—C10—C11—C120.4 (2)
C2—C3—C4—C5179.9 (2)C9—C10—C11—C12179.81 (15)
C3—C4—C5—C60.9 (4)C10—C11—C12—C130.4 (2)
C4—C5—C6—C71.2 (3)C11—C12—C13—C140.1 (3)
C3—N2—C7—C60.6 (3)C10—N3—C14—C130.6 (3)
C5—C6—C7—N20.5 (3)C12—C13—C14—N30.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N3i0.90 (3)1.94 (3)2.8174 (18)164 (2)
Symmetry code: (i) x+1, y, z.
 

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