Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the asymmetric unit of the title compound, C13H14N2O2, there are one complete mol­ecule and two half-mol­ecules; in each of the latter a twofold rotation axis passes through the central C atom. In the crystal structure, a three-dimensional network is formed though inter­molecular N—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019258/lh2080sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019258/lh2080Isup2.hkl
Contains datablock I

CCDC reference: 610848

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.129
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT410_ALERT_2_C Short Intra H...H Contact H1C .. H12 .. 1.99 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Bis(4-aminophenoxy)methane top
Crystal data top
C13H14N2O2F(000) = 1952
Mr = 230.26Dx = 1.341 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5124 reflections
a = 29.375 (4) Åθ = 4.2–25.6°
b = 9.6601 (10) ŵ = 0.09 mm1
c = 17.090 (2) ÅT = 173 K
β = 109.867 (9)°Needle, colourless
V = 4560.9 (10) Å30.18 × 0.09 × 0.07 mm
Z = 16
Data collection top
Stoe IPDS-II two-circle
diffractometer
1628 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.097
Graphite monochromatorθmax = 25.6°, θmin = 3.5°
ω scansh = 3535
13252 measured reflectionsk = 1111
4243 independent reflectionsl = 2017
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)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0464P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
4243 reflectionsΔρmax = 0.22 e Å3
333 parametersΔρmin = 0.22 e Å3
8 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00159 (14)
Special details top

Experimental. 13C NMR (CDCl3): δ 93.4, 116.1, 118.1, 141.5, 150.0.

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
xyzUiso*/Ueq
C10.24582 (12)0.3880 (4)0.2441 (2)0.0270 (11)
H1C0.27290.32460.24730.032*
H1D0.21700.33120.23970.032*
O10.23574 (8)0.4728 (2)0.17236 (18)0.0258 (7)
O20.25836 (8)0.4699 (2)0.31762 (18)0.0282 (7)
N10.38462 (11)0.6598 (3)0.0623 (2)0.0267 (8)
H1A0.3810 (11)0.7491 (16)0.043 (2)0.032*
H1B0.4146 (6)0.638 (3)0.0977 (17)0.032*
N20.11562 (11)0.6703 (3)0.4393 (2)0.0260 (8)
H2A0.0848 (6)0.687 (3)0.4047 (18)0.031*
H2B0.1272 (11)0.734 (3)0.4807 (15)0.031*
C110.27526 (12)0.5194 (3)0.1508 (2)0.0185 (9)
C120.31559 (11)0.4372 (3)0.1600 (2)0.0230 (8)
H120.31830.34810.18460.028*
C130.35204 (11)0.4877 (3)0.1323 (2)0.0218 (8)
H130.37990.43240.13920.026*
C140.34842 (13)0.6174 (4)0.0948 (3)0.0202 (9)
C150.30782 (11)0.6977 (3)0.0861 (2)0.0210 (8)
H150.30480.78650.06090.025*
C160.27145 (11)0.6488 (3)0.1140 (2)0.0228 (9)
H160.24380.70460.10790.027*
C210.22089 (12)0.5220 (3)0.3434 (3)0.0193 (9)
C220.23467 (11)0.5686 (3)0.4245 (2)0.0221 (8)
H220.26780.56730.45870.027*
C230.19963 (11)0.6175 (3)0.4559 (2)0.0217 (8)
H230.20910.64780.51200.026*
C240.15053 (13)0.6228 (3)0.4056 (3)0.0204 (9)
C250.13789 (11)0.5763 (3)0.3240 (2)0.0224 (8)
H250.10490.57860.28930.027*
C260.17247 (10)0.5264 (3)0.2918 (2)0.0221 (8)
H260.16320.49590.23570.026*
C1A0.00000.6430 (5)0.75000.0278 (14)
H1A30.02790.58240.74610.033*
O1A0.01139 (9)0.7219 (2)0.67631 (18)0.0273 (7)
N1A0.13880 (11)0.9107 (3)0.5696 (2)0.0263 (8)
H1A10.1261 (10)0.978 (3)0.5301 (16)0.032*
H1A20.1663 (7)0.941 (3)0.6104 (16)0.032*
C11A0.02832 (13)0.7705 (3)0.6557 (3)0.0214 (10)
C12A0.07581 (11)0.7701 (3)0.7093 (2)0.0204 (8)
H12A0.08350.73750.76480.025*
C13A0.11226 (11)0.8184 (3)0.6807 (2)0.0199 (8)
H13A0.14490.81820.71740.024*
C14A0.10169 (12)0.8671 (4)0.5992 (3)0.0186 (9)
C15A0.05346 (11)0.8677 (3)0.5471 (2)0.0220 (8)
H15A0.04550.90150.49190.026*
C16A0.01668 (11)0.8199 (3)0.5745 (2)0.0191 (8)
H16A0.01600.82080.53820.023*
C1B0.50000.6154 (5)0.75000.0293 (14)
H1B30.47240.55510.74790.035*
O1B0.51277 (9)0.6975 (2)0.82291 (18)0.0275 (7)
N1B0.37199 (11)0.9180 (3)0.9435 (2)0.0304 (9)
H1B10.3794 (11)1.0052 (17)0.964 (2)0.036*
H1B20.3433 (7)0.916 (3)0.9017 (16)0.036*
C11B0.47434 (12)0.7525 (4)0.8445 (3)0.0218 (10)
C12B0.48213 (11)0.8810 (3)0.8828 (2)0.0223 (8)
H12B0.51100.93040.88810.027*
C13B0.44787 (11)0.9388 (3)0.9137 (2)0.0227 (9)
H13B0.45361.02710.93970.027*
C14B0.40527 (13)0.8670 (4)0.9065 (3)0.0210 (9)
C15B0.39824 (11)0.7374 (3)0.8686 (2)0.0244 (9)
H15B0.36970.68670.86390.029*
C16B0.43219 (11)0.6803 (3)0.8373 (2)0.0218 (8)
H16B0.42650.59220.81110.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.033 (2)0.026 (2)0.028 (3)0.0036 (15)0.017 (2)0.0019 (19)
O10.0240 (13)0.0346 (14)0.0220 (18)0.0028 (11)0.0120 (12)0.0011 (14)
O20.0223 (14)0.0391 (15)0.0256 (19)0.0003 (12)0.0113 (13)0.0011 (15)
N10.0250 (17)0.0310 (18)0.026 (2)0.0008 (15)0.0108 (16)0.0006 (18)
N20.0240 (17)0.0276 (18)0.029 (2)0.0000 (15)0.0125 (16)0.0041 (17)
C110.019 (2)0.0236 (19)0.014 (3)0.0022 (15)0.0068 (17)0.0081 (18)
C120.032 (2)0.0190 (18)0.021 (2)0.0028 (14)0.0125 (17)0.0016 (17)
C130.0255 (18)0.0229 (19)0.019 (2)0.0044 (14)0.0104 (16)0.0009 (17)
C140.023 (2)0.022 (2)0.018 (3)0.0037 (16)0.0098 (18)0.0034 (19)
C150.0276 (19)0.0198 (18)0.015 (2)0.0011 (14)0.0062 (16)0.0004 (16)
C160.0265 (19)0.0206 (18)0.022 (2)0.0054 (14)0.0095 (16)0.0009 (17)
C210.021 (2)0.0207 (18)0.019 (3)0.0011 (15)0.0105 (18)0.0049 (19)
C220.0201 (17)0.0261 (19)0.018 (2)0.0013 (14)0.0035 (15)0.0046 (18)
C230.0253 (18)0.0199 (17)0.020 (2)0.0012 (14)0.0073 (16)0.0012 (17)
C240.027 (2)0.0130 (18)0.026 (3)0.0036 (15)0.0150 (19)0.0001 (19)
C250.0162 (16)0.0224 (18)0.027 (2)0.0004 (14)0.0052 (15)0.0055 (18)
C260.0245 (18)0.0216 (17)0.017 (2)0.0030 (14)0.0026 (15)0.0025 (17)
C1A0.040 (3)0.020 (3)0.031 (4)0.0000.022 (3)0.000
O1A0.0236 (14)0.0366 (15)0.026 (2)0.0009 (12)0.0140 (13)0.0014 (15)
N1A0.0259 (18)0.0306 (19)0.027 (2)0.0052 (15)0.0151 (16)0.0001 (18)
C11A0.023 (2)0.0212 (19)0.024 (3)0.0014 (16)0.014 (2)0.003 (2)
C12A0.0248 (18)0.0221 (18)0.017 (2)0.0019 (14)0.0106 (16)0.0016 (17)
C13A0.0200 (17)0.0180 (17)0.022 (2)0.0016 (13)0.0074 (15)0.0035 (17)
C14A0.0176 (18)0.0201 (19)0.019 (3)0.0007 (15)0.0074 (17)0.0068 (19)
C15A0.0289 (19)0.0211 (18)0.016 (2)0.0027 (14)0.0078 (16)0.0008 (17)
C16A0.0138 (17)0.0176 (17)0.024 (2)0.0020 (13)0.0041 (15)0.0012 (17)
C1B0.042 (3)0.027 (3)0.026 (4)0.0000.021 (3)0.000
O1B0.0252 (14)0.0404 (16)0.0200 (18)0.0036 (11)0.0116 (13)0.0000 (14)
N1B0.0311 (18)0.0282 (18)0.035 (3)0.0024 (15)0.0158 (17)0.0037 (19)
C11B0.024 (2)0.0222 (19)0.022 (3)0.0000 (16)0.0110 (19)0.0005 (19)
C12B0.0190 (17)0.0277 (19)0.020 (2)0.0029 (14)0.0056 (15)0.0053 (18)
C13B0.0284 (19)0.0159 (18)0.023 (2)0.0042 (14)0.0073 (16)0.0005 (16)
C14B0.026 (2)0.021 (2)0.016 (3)0.0045 (15)0.0064 (18)0.0041 (18)
C15B0.0205 (18)0.027 (2)0.026 (3)0.0051 (14)0.0077 (16)0.0018 (18)
C16B0.028 (2)0.0190 (18)0.020 (2)0.0046 (14)0.0096 (17)0.0010 (17)
Geometric parameters (Å, º) top
C1—O11.419 (4)C1A—O1Ai1.412 (4)
C1—O21.423 (4)C1A—H1A30.9900
C1—H1C0.9900O1A—C11A1.409 (4)
C1—H1D0.9900N1A—C14A1.413 (5)
O1—C111.406 (4)N1A—H1A10.92 (3)
O2—C211.410 (4)N1A—H1A20.92 (3)
N1—C141.417 (5)C11A—C12A1.385 (5)
N1—H1A0.92 (3)C11A—C16A1.395 (5)
N1—H1B0.91 (3)C12A—C13A1.400 (4)
N2—C241.412 (5)C12A—H12A0.9500
N2—H2A0.91 (3)C13A—C14A1.402 (5)
N2—H2B0.91 (3)C13A—H13A0.9500
C11—C161.387 (5)C14A—C15A1.394 (5)
C11—C121.390 (4)C15A—C16A1.394 (4)
C12—C131.397 (4)C15A—H15A0.9500
C12—H120.9500C16A—H16A0.9500
C13—C141.395 (5)C1B—O1B1.416 (4)
C13—H130.9500C1B—O1Bii1.416 (4)
C14—C151.388 (4)C1B—H1B30.9900
C15—C161.393 (4)O1B—C11B1.406 (4)
C15—H150.9500N1B—C14B1.420 (5)
C16—H160.9500N1B—H1B10.91 (3)
C21—C221.381 (5)N1B—H1B20.90 (3)
C21—C261.396 (4)C11B—C12B1.385 (5)
C22—C231.395 (4)C11B—C16B1.389 (4)
C22—H220.9500C12B—C13B1.403 (4)
C23—C241.406 (5)C12B—H12B0.9500
C23—H230.9500C13B—C14B1.399 (4)
C24—C251.390 (5)C13B—H13B0.9500
C25—C261.395 (4)C14B—C15B1.393 (5)
C25—H250.9500C15B—C16B1.395 (4)
C26—H260.9500C15B—H15B0.9500
C1A—O1A1.412 (4)C16B—H16B0.9500
O1—C1—O2111.0 (3)O1A—C1A—O1Ai114.6 (4)
O1—C1—H1C109.4O1A—C1A—H1A3108.6
O2—C1—H1C109.4O1Ai—C1A—H1A3108.6
O1—C1—H1D109.4C11A—O1A—C1A116.0 (3)
O2—C1—H1D109.4C14A—N1A—H1A1108 (2)
H1C—C1—H1D108.0C14A—N1A—H1A2114 (2)
C11—O1—C1117.6 (3)H1A1—N1A—H1A2111 (3)
C21—O2—C1118.6 (3)C12A—C11A—C16A120.7 (3)
C14—N1—H1A114 (2)C12A—C11A—O1A124.5 (4)
C14—N1—H1B111 (2)C16A—C11A—O1A114.8 (3)
H1A—N1—H1B115 (3)C11A—C12A—C13A119.1 (4)
C24—N2—H2A120 (2)C11A—C12A—H12A120.5
C24—N2—H2B114 (2)C13A—C12A—H12A120.5
H2A—N2—H2B114 (3)C12A—C13A—C14A121.4 (3)
C16—C11—C12120.0 (3)C12A—C13A—H13A119.3
C16—C11—O1117.4 (3)C14A—C13A—H13A119.3
C12—C11—O1122.4 (3)C15A—C14A—C13A118.0 (3)
C11—C12—C13119.0 (3)C15A—C14A—N1A120.7 (4)
C11—C12—H12120.5C13A—C14A—N1A121.2 (3)
C13—C12—H12120.5C14A—C15A—C16A121.3 (4)
C14—C13—C12121.4 (3)C14A—C15A—H15A119.4
C14—C13—H13119.3C16A—C15A—H15A119.4
C12—C13—H13119.3C15A—C16A—C11A119.4 (3)
C15—C14—C13118.7 (3)C15A—C16A—H16A120.3
C15—C14—N1121.9 (3)C11A—C16A—H16A120.3
C13—C14—N1119.3 (3)O1B—C1B—O1Bii111.9 (4)
C14—C15—C16120.3 (3)O1B—C1B—H1B3109.2
C14—C15—H15119.8O1Bii—C1B—H1B3109.2
C16—C15—H15119.8C11B—O1B—C1B116.5 (3)
C11—C16—C15120.5 (3)C14B—N1B—H1B1113 (2)
C11—C16—H16119.7C14B—N1B—H1B2104 (2)
C15—C16—H16119.7H1B1—N1B—H1B2112 (3)
C22—C21—C26120.8 (3)C12B—C11B—C16B119.4 (3)
C22—C21—O2115.9 (3)C12B—C11B—O1B116.4 (3)
C26—C21—O2123.4 (4)C16B—C11B—O1B123.9 (3)
C21—C22—C23119.6 (3)C11B—C12B—C13B120.7 (3)
C21—C22—H22120.2C11B—C12B—H12B119.6
C23—C22—H22120.2C13B—C12B—H12B119.6
C22—C23—C24121.0 (4)C14B—C13B—C12B120.3 (3)
C22—C23—H23119.5C14B—C13B—H13B119.9
C24—C23—H23119.5C12B—C13B—H13B119.9
C25—C24—C23118.0 (3)C15B—C14B—C13B118.3 (3)
C25—C24—N2122.0 (3)C15B—C14B—N1B120.2 (3)
C23—C24—N2119.9 (4)C13B—C14B—N1B121.3 (3)
C24—C25—C26121.7 (3)C14B—C15B—C16B121.4 (3)
C24—C25—H25119.2C14B—C15B—H15B119.3
C26—C25—H25119.2C16B—C15B—H15B119.3
C25—C26—C21118.9 (3)C11B—C16B—C15B120.0 (3)
C25—C26—H26120.5C11B—C16B—H16B120.0
C21—C26—H26120.5C15B—C16B—H16B120.0
O2—C1—O1—C1183.0 (3)O1Ai—C1A—O1A—C11A82.6 (3)
O1—C1—O2—C2185.5 (3)C1A—O1A—C11A—C12A13.4 (5)
C1—O1—C11—C16147.0 (3)C1A—O1A—C11A—C16A166.0 (3)
C1—O1—C11—C1237.5 (5)C16A—C11A—C12A—C13A0.8 (5)
C16—C11—C12—C130.6 (5)O1A—C11A—C12A—C13A178.5 (3)
O1—C11—C12—C13176.0 (3)C11A—C12A—C13A—C14A0.1 (5)
C11—C12—C13—C140.9 (5)C12A—C13A—C14A—C15A0.7 (5)
C12—C13—C14—C150.8 (5)C12A—C13A—C14A—N1A177.5 (3)
C12—C13—C14—N1175.4 (4)C13A—C14A—C15A—C16A0.8 (5)
C13—C14—C15—C160.2 (6)N1A—C14A—C15A—C16A177.4 (3)
N1—C14—C15—C16175.8 (4)C14A—C15A—C16A—C11A0.1 (5)
C12—C11—C16—C150.1 (5)C12A—C11A—C16A—C15A0.7 (5)
O1—C11—C16—C15175.8 (3)O1A—C11A—C16A—C15A178.7 (3)
C14—C15—C16—C110.1 (6)O1Bii—C1B—O1B—C11B80.0 (3)
C1—O2—C21—C22163.7 (3)C1B—O1B—C11B—C12B146.8 (3)
C1—O2—C21—C2615.6 (5)C1B—O1B—C11B—C16B39.9 (5)
C26—C21—C22—C231.5 (5)C16B—C11B—C12B—C13B0.4 (6)
O2—C21—C22—C23177.8 (3)O1B—C11B—C12B—C13B174.0 (3)
C21—C22—C23—C241.3 (5)C11B—C12B—C13B—C14B0.2 (6)
C22—C23—C24—C250.7 (5)C12B—C13B—C14B—C15B0.5 (6)
C22—C23—C24—N2178.8 (3)C12B—C13B—C14B—N1B174.6 (4)
C23—C24—C25—C260.4 (5)C13B—C14B—C15B—C16B0.9 (6)
N2—C24—C25—C26178.4 (3)N1B—C14B—C15B—C16B175.1 (4)
C24—C25—C26—C210.6 (5)C12B—C11B—C16B—C15B0.0 (6)
C22—C21—C26—C251.2 (5)O1B—C11B—C16B—C15B173.0 (4)
O2—C21—C26—C25178.1 (3)C14B—C15B—C16B—C11B0.7 (6)
Symmetry codes: (i) x, y, z+3/2; (ii) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N1Biii0.92 (3)2.31 (2)3.158 (5)154 (3)
N1—H1B···O1Aiv0.91 (3)2.52 (2)3.223 (4)134 (3)
N2—H2A···O1Bv0.91 (2)2.38 (2)3.261 (4)163 (3)
N2—H2B···N1A0.91 (3)2.23 (3)3.129 (5)167 (3)
N1A—H1A1···N1vi0.92 (3)2.31 (3)3.208 (5)165 (3)
N1A—H1A2···O2vii0.92 (3)2.30 (1)3.196 (4)165 (3)
N1B—H1B1···N2viii0.91 (3)2.26 (2)3.097 (5)152 (3)
N1B—H1B2···O1vii0.90 (3)2.48 (2)3.285 (4)149 (3)
Symmetry codes: (iii) x, y, z1; (iv) x+1/2, y+3/2, z1/2; (v) x1/2, y+3/2, z1/2; (vi) x+1/2, y+1/2, z+1/2; (vii) x+1/2, y+3/2, z+1; (viii) x+1/2, y+1/2, z+3/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds