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In the asymmetric unit of the title compound, C
13H
14N
2O
2, 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
CCDC reference: 610848
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C13H14N2O2 | F(000) = 1952 |
Mr = 230.26 | Dx = 1.341 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5124 reflections |
a = 29.375 (4) Å | θ = 4.2–25.6° |
b = 9.6601 (10) Å | µ = 0.09 mm−1 |
c = 17.090 (2) Å | T = 173 K |
β = 109.867 (9)° | Needle, colourless |
V = 4560.9 (10) Å3 | 0.18 × 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 tube | Rint = 0.097 |
Graphite monochromator | θmax = 25.6°, θmin = 3.5° |
ω scans | h = −35→35 |
13252 measured reflections | k = −11→11 |
4243 independent reflections | l = −20→17 |
Refinement top
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)] = 0.050 | H 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 reflections | Δρmax = 0.22 e Å−3 |
333 parameters | Δρmin = −0.22 e Å−3 |
8 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.24582 (12) | 0.3880 (4) | 0.2441 (2) | 0.0270 (11) | |
H1C | 0.2729 | 0.3246 | 0.2473 | 0.032* | |
H1D | 0.2170 | 0.3312 | 0.2397 | 0.032* | |
O1 | 0.23574 (8) | 0.4728 (2) | 0.17236 (18) | 0.0258 (7) | |
O2 | 0.25836 (8) | 0.4699 (2) | 0.31762 (18) | 0.0282 (7) | |
N1 | 0.38462 (11) | 0.6598 (3) | 0.0623 (2) | 0.0267 (8) | |
H1A | 0.3810 (11) | 0.7491 (16) | 0.043 (2) | 0.032* | |
H1B | 0.4146 (6) | 0.638 (3) | 0.0977 (17) | 0.032* | |
N2 | 0.11562 (11) | 0.6703 (3) | 0.4393 (2) | 0.0260 (8) | |
H2A | 0.0848 (6) | 0.687 (3) | 0.4047 (18) | 0.031* | |
H2B | 0.1272 (11) | 0.734 (3) | 0.4807 (15) | 0.031* | |
C11 | 0.27526 (12) | 0.5194 (3) | 0.1508 (2) | 0.0185 (9) | |
C12 | 0.31559 (11) | 0.4372 (3) | 0.1600 (2) | 0.0230 (8) | |
H12 | 0.3183 | 0.3481 | 0.1846 | 0.028* | |
C13 | 0.35204 (11) | 0.4877 (3) | 0.1323 (2) | 0.0218 (8) | |
H13 | 0.3799 | 0.4324 | 0.1392 | 0.026* | |
C14 | 0.34842 (13) | 0.6174 (4) | 0.0948 (3) | 0.0202 (9) | |
C15 | 0.30782 (11) | 0.6977 (3) | 0.0861 (2) | 0.0210 (8) | |
H15 | 0.3048 | 0.7865 | 0.0609 | 0.025* | |
C16 | 0.27145 (11) | 0.6488 (3) | 0.1140 (2) | 0.0228 (9) | |
H16 | 0.2438 | 0.7046 | 0.1079 | 0.027* | |
C21 | 0.22089 (12) | 0.5220 (3) | 0.3434 (3) | 0.0193 (9) | |
C22 | 0.23467 (11) | 0.5686 (3) | 0.4245 (2) | 0.0221 (8) | |
H22 | 0.2678 | 0.5673 | 0.4587 | 0.027* | |
C23 | 0.19963 (11) | 0.6175 (3) | 0.4559 (2) | 0.0217 (8) | |
H23 | 0.2091 | 0.6478 | 0.5120 | 0.026* | |
C24 | 0.15053 (13) | 0.6228 (3) | 0.4056 (3) | 0.0204 (9) | |
C25 | 0.13789 (11) | 0.5763 (3) | 0.3240 (2) | 0.0224 (8) | |
H25 | 0.1049 | 0.5786 | 0.2893 | 0.027* | |
C26 | 0.17247 (10) | 0.5264 (3) | 0.2918 (2) | 0.0221 (8) | |
H26 | 0.1632 | 0.4959 | 0.2357 | 0.026* | |
C1A | 0.0000 | 0.6430 (5) | 0.7500 | 0.0278 (14) | |
H1A3 | −0.0279 | 0.5824 | 0.7461 | 0.033* | |
O1A | −0.01139 (9) | 0.7219 (2) | 0.67631 (18) | 0.0273 (7) | |
N1A | 0.13880 (11) | 0.9107 (3) | 0.5696 (2) | 0.0263 (8) | |
H1A1 | 0.1261 (10) | 0.978 (3) | 0.5301 (16) | 0.032* | |
H1A2 | 0.1663 (7) | 0.941 (3) | 0.6104 (16) | 0.032* | |
C11A | 0.02832 (13) | 0.7705 (3) | 0.6557 (3) | 0.0214 (10) | |
C12A | 0.07581 (11) | 0.7701 (3) | 0.7093 (2) | 0.0204 (8) | |
H12A | 0.0835 | 0.7375 | 0.7648 | 0.025* | |
C13A | 0.11226 (11) | 0.8184 (3) | 0.6807 (2) | 0.0199 (8) | |
H13A | 0.1449 | 0.8182 | 0.7174 | 0.024* | |
C14A | 0.10169 (12) | 0.8671 (4) | 0.5992 (3) | 0.0186 (9) | |
C15A | 0.05346 (11) | 0.8677 (3) | 0.5471 (2) | 0.0220 (8) | |
H15A | 0.0455 | 0.9015 | 0.4919 | 0.026* | |
C16A | 0.01668 (11) | 0.8199 (3) | 0.5745 (2) | 0.0191 (8) | |
H16A | −0.0160 | 0.8208 | 0.5382 | 0.023* | |
C1B | 0.5000 | 0.6154 (5) | 0.7500 | 0.0293 (14) | |
H1B3 | 0.4724 | 0.5551 | 0.7479 | 0.035* | |
O1B | 0.51277 (9) | 0.6975 (2) | 0.82291 (18) | 0.0275 (7) | |
N1B | 0.37199 (11) | 0.9180 (3) | 0.9435 (2) | 0.0304 (9) | |
H1B1 | 0.3794 (11) | 1.0052 (17) | 0.964 (2) | 0.036* | |
H1B2 | 0.3433 (7) | 0.916 (3) | 0.9017 (16) | 0.036* | |
C11B | 0.47434 (12) | 0.7525 (4) | 0.8445 (3) | 0.0218 (10) | |
C12B | 0.48213 (11) | 0.8810 (3) | 0.8828 (2) | 0.0223 (8) | |
H12B | 0.5110 | 0.9304 | 0.8881 | 0.027* | |
C13B | 0.44787 (11) | 0.9388 (3) | 0.9137 (2) | 0.0227 (9) | |
H13B | 0.4536 | 1.0271 | 0.9397 | 0.027* | |
C14B | 0.40527 (13) | 0.8670 (4) | 0.9065 (3) | 0.0210 (9) | |
C15B | 0.39824 (11) | 0.7374 (3) | 0.8686 (2) | 0.0244 (9) | |
H15B | 0.3697 | 0.6867 | 0.8639 | 0.029* | |
C16B | 0.43219 (11) | 0.6803 (3) | 0.8373 (2) | 0.0218 (8) | |
H16B | 0.4265 | 0.5922 | 0.8111 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.033 (2) | 0.026 (2) | 0.028 (3) | −0.0036 (15) | 0.017 (2) | −0.0019 (19) |
O1 | 0.0240 (13) | 0.0346 (14) | 0.0220 (18) | −0.0028 (11) | 0.0120 (12) | 0.0011 (14) |
O2 | 0.0223 (14) | 0.0391 (15) | 0.0256 (19) | 0.0003 (12) | 0.0113 (13) | −0.0011 (15) |
N1 | 0.0250 (17) | 0.0310 (18) | 0.026 (2) | 0.0008 (15) | 0.0108 (16) | 0.0006 (18) |
N2 | 0.0240 (17) | 0.0276 (18) | 0.029 (2) | 0.0000 (15) | 0.0125 (16) | −0.0041 (17) |
C11 | 0.019 (2) | 0.0236 (19) | 0.014 (3) | −0.0022 (15) | 0.0068 (17) | −0.0081 (18) |
C12 | 0.032 (2) | 0.0190 (18) | 0.021 (2) | 0.0028 (14) | 0.0125 (17) | 0.0016 (17) |
C13 | 0.0255 (18) | 0.0229 (19) | 0.019 (2) | 0.0044 (14) | 0.0104 (16) | 0.0009 (17) |
C14 | 0.023 (2) | 0.022 (2) | 0.018 (3) | −0.0037 (16) | 0.0098 (18) | −0.0034 (19) |
C15 | 0.0276 (19) | 0.0198 (18) | 0.015 (2) | 0.0011 (14) | 0.0062 (16) | −0.0004 (16) |
C16 | 0.0265 (19) | 0.0206 (18) | 0.022 (2) | 0.0054 (14) | 0.0095 (16) | −0.0009 (17) |
C21 | 0.021 (2) | 0.0207 (18) | 0.019 (3) | −0.0011 (15) | 0.0105 (18) | 0.0049 (19) |
C22 | 0.0201 (17) | 0.0261 (19) | 0.018 (2) | −0.0013 (14) | 0.0035 (15) | 0.0046 (18) |
C23 | 0.0253 (18) | 0.0199 (17) | 0.020 (2) | −0.0012 (14) | 0.0073 (16) | 0.0012 (17) |
C24 | 0.027 (2) | 0.0130 (18) | 0.026 (3) | −0.0036 (15) | 0.0150 (19) | 0.0001 (19) |
C25 | 0.0162 (16) | 0.0224 (18) | 0.027 (2) | −0.0004 (14) | 0.0052 (15) | 0.0055 (18) |
C26 | 0.0245 (18) | 0.0216 (17) | 0.017 (2) | −0.0030 (14) | 0.0026 (15) | 0.0025 (17) |
C1A | 0.040 (3) | 0.020 (3) | 0.031 (4) | 0.000 | 0.022 (3) | 0.000 |
O1A | 0.0236 (14) | 0.0366 (15) | 0.026 (2) | −0.0009 (12) | 0.0140 (13) | 0.0014 (15) |
N1A | 0.0259 (18) | 0.0306 (19) | 0.027 (2) | −0.0052 (15) | 0.0151 (16) | 0.0001 (18) |
C11A | 0.023 (2) | 0.0212 (19) | 0.024 (3) | −0.0014 (16) | 0.014 (2) | −0.003 (2) |
C12A | 0.0248 (18) | 0.0221 (18) | 0.017 (2) | 0.0019 (14) | 0.0106 (16) | 0.0016 (17) |
C13A | 0.0200 (17) | 0.0180 (17) | 0.022 (2) | 0.0016 (13) | 0.0074 (15) | −0.0035 (17) |
C14A | 0.0176 (18) | 0.0201 (19) | 0.019 (3) | −0.0007 (15) | 0.0074 (17) | −0.0068 (19) |
C15A | 0.0289 (19) | 0.0211 (18) | 0.016 (2) | 0.0027 (14) | 0.0078 (16) | 0.0008 (17) |
C16A | 0.0138 (17) | 0.0176 (17) | 0.024 (2) | 0.0020 (13) | 0.0041 (15) | −0.0012 (17) |
C1B | 0.042 (3) | 0.027 (3) | 0.026 (4) | 0.000 | 0.021 (3) | 0.000 |
O1B | 0.0252 (14) | 0.0404 (16) | 0.0200 (18) | 0.0036 (11) | 0.0116 (13) | 0.0000 (14) |
N1B | 0.0311 (18) | 0.0282 (18) | 0.035 (3) | 0.0024 (15) | 0.0158 (17) | −0.0037 (19) |
C11B | 0.024 (2) | 0.0222 (19) | 0.022 (3) | 0.0000 (16) | 0.0110 (19) | 0.0005 (19) |
C12B | 0.0190 (17) | 0.0277 (19) | 0.020 (2) | −0.0029 (14) | 0.0056 (15) | 0.0053 (18) |
C13B | 0.0284 (19) | 0.0159 (18) | 0.023 (2) | −0.0042 (14) | 0.0073 (16) | 0.0005 (16) |
C14B | 0.026 (2) | 0.021 (2) | 0.016 (3) | 0.0045 (15) | 0.0064 (18) | 0.0041 (18) |
C15B | 0.0205 (18) | 0.027 (2) | 0.026 (3) | −0.0051 (14) | 0.0077 (16) | 0.0018 (18) |
C16B | 0.028 (2) | 0.0190 (18) | 0.020 (2) | −0.0046 (14) | 0.0096 (17) | −0.0010 (17) |
Geometric parameters (Å, º) top
C1—O1 | 1.419 (4) | C1A—O1Ai | 1.412 (4) |
C1—O2 | 1.423 (4) | C1A—H1A3 | 0.9900 |
C1—H1C | 0.9900 | O1A—C11A | 1.409 (4) |
C1—H1D | 0.9900 | N1A—C14A | 1.413 (5) |
O1—C11 | 1.406 (4) | N1A—H1A1 | 0.92 (3) |
O2—C21 | 1.410 (4) | N1A—H1A2 | 0.92 (3) |
N1—C14 | 1.417 (5) | C11A—C12A | 1.385 (5) |
N1—H1A | 0.92 (3) | C11A—C16A | 1.395 (5) |
N1—H1B | 0.91 (3) | C12A—C13A | 1.400 (4) |
N2—C24 | 1.412 (5) | C12A—H12A | 0.9500 |
N2—H2A | 0.91 (3) | C13A—C14A | 1.402 (5) |
N2—H2B | 0.91 (3) | C13A—H13A | 0.9500 |
C11—C16 | 1.387 (5) | C14A—C15A | 1.394 (5) |
C11—C12 | 1.390 (4) | C15A—C16A | 1.394 (4) |
C12—C13 | 1.397 (4) | C15A—H15A | 0.9500 |
C12—H12 | 0.9500 | C16A—H16A | 0.9500 |
C13—C14 | 1.395 (5) | C1B—O1B | 1.416 (4) |
C13—H13 | 0.9500 | C1B—O1Bii | 1.416 (4) |
C14—C15 | 1.388 (4) | C1B—H1B3 | 0.9900 |
C15—C16 | 1.393 (4) | O1B—C11B | 1.406 (4) |
C15—H15 | 0.9500 | N1B—C14B | 1.420 (5) |
C16—H16 | 0.9500 | N1B—H1B1 | 0.91 (3) |
C21—C22 | 1.381 (5) | N1B—H1B2 | 0.90 (3) |
C21—C26 | 1.396 (4) | C11B—C12B | 1.385 (5) |
C22—C23 | 1.395 (4) | C11B—C16B | 1.389 (4) |
C22—H22 | 0.9500 | C12B—C13B | 1.403 (4) |
C23—C24 | 1.406 (5) | C12B—H12B | 0.9500 |
C23—H23 | 0.9500 | C13B—C14B | 1.399 (4) |
C24—C25 | 1.390 (5) | C13B—H13B | 0.9500 |
C25—C26 | 1.395 (4) | C14B—C15B | 1.393 (5) |
C25—H25 | 0.9500 | C15B—C16B | 1.395 (4) |
C26—H26 | 0.9500 | C15B—H15B | 0.9500 |
C1A—O1A | 1.412 (4) | C16B—H16B | 0.9500 |
| | | |
O1—C1—O2 | 111.0 (3) | O1A—C1A—O1Ai | 114.6 (4) |
O1—C1—H1C | 109.4 | O1A—C1A—H1A3 | 108.6 |
O2—C1—H1C | 109.4 | O1Ai—C1A—H1A3 | 108.6 |
O1—C1—H1D | 109.4 | C11A—O1A—C1A | 116.0 (3) |
O2—C1—H1D | 109.4 | C14A—N1A—H1A1 | 108 (2) |
H1C—C1—H1D | 108.0 | C14A—N1A—H1A2 | 114 (2) |
C11—O1—C1 | 117.6 (3) | H1A1—N1A—H1A2 | 111 (3) |
C21—O2—C1 | 118.6 (3) | C12A—C11A—C16A | 120.7 (3) |
C14—N1—H1A | 114 (2) | C12A—C11A—O1A | 124.5 (4) |
C14—N1—H1B | 111 (2) | C16A—C11A—O1A | 114.8 (3) |
H1A—N1—H1B | 115 (3) | C11A—C12A—C13A | 119.1 (4) |
C24—N2—H2A | 120 (2) | C11A—C12A—H12A | 120.5 |
C24—N2—H2B | 114 (2) | C13A—C12A—H12A | 120.5 |
H2A—N2—H2B | 114 (3) | C12A—C13A—C14A | 121.4 (3) |
C16—C11—C12 | 120.0 (3) | C12A—C13A—H13A | 119.3 |
C16—C11—O1 | 117.4 (3) | C14A—C13A—H13A | 119.3 |
C12—C11—O1 | 122.4 (3) | C15A—C14A—C13A | 118.0 (3) |
C11—C12—C13 | 119.0 (3) | C15A—C14A—N1A | 120.7 (4) |
C11—C12—H12 | 120.5 | C13A—C14A—N1A | 121.2 (3) |
C13—C12—H12 | 120.5 | C14A—C15A—C16A | 121.3 (4) |
C14—C13—C12 | 121.4 (3) | C14A—C15A—H15A | 119.4 |
C14—C13—H13 | 119.3 | C16A—C15A—H15A | 119.4 |
C12—C13—H13 | 119.3 | C15A—C16A—C11A | 119.4 (3) |
C15—C14—C13 | 118.7 (3) | C15A—C16A—H16A | 120.3 |
C15—C14—N1 | 121.9 (3) | C11A—C16A—H16A | 120.3 |
C13—C14—N1 | 119.3 (3) | O1B—C1B—O1Bii | 111.9 (4) |
C14—C15—C16 | 120.3 (3) | O1B—C1B—H1B3 | 109.2 |
C14—C15—H15 | 119.8 | O1Bii—C1B—H1B3 | 109.2 |
C16—C15—H15 | 119.8 | C11B—O1B—C1B | 116.5 (3) |
C11—C16—C15 | 120.5 (3) | C14B—N1B—H1B1 | 113 (2) |
C11—C16—H16 | 119.7 | C14B—N1B—H1B2 | 104 (2) |
C15—C16—H16 | 119.7 | H1B1—N1B—H1B2 | 112 (3) |
C22—C21—C26 | 120.8 (3) | C12B—C11B—C16B | 119.4 (3) |
C22—C21—O2 | 115.9 (3) | C12B—C11B—O1B | 116.4 (3) |
C26—C21—O2 | 123.4 (4) | C16B—C11B—O1B | 123.9 (3) |
C21—C22—C23 | 119.6 (3) | C11B—C12B—C13B | 120.7 (3) |
C21—C22—H22 | 120.2 | C11B—C12B—H12B | 119.6 |
C23—C22—H22 | 120.2 | C13B—C12B—H12B | 119.6 |
C22—C23—C24 | 121.0 (4) | C14B—C13B—C12B | 120.3 (3) |
C22—C23—H23 | 119.5 | C14B—C13B—H13B | 119.9 |
C24—C23—H23 | 119.5 | C12B—C13B—H13B | 119.9 |
C25—C24—C23 | 118.0 (3) | C15B—C14B—C13B | 118.3 (3) |
C25—C24—N2 | 122.0 (3) | C15B—C14B—N1B | 120.2 (3) |
C23—C24—N2 | 119.9 (4) | C13B—C14B—N1B | 121.3 (3) |
C24—C25—C26 | 121.7 (3) | C14B—C15B—C16B | 121.4 (3) |
C24—C25—H25 | 119.2 | C14B—C15B—H15B | 119.3 |
C26—C25—H25 | 119.2 | C16B—C15B—H15B | 119.3 |
C25—C26—C21 | 118.9 (3) | C11B—C16B—C15B | 120.0 (3) |
C25—C26—H26 | 120.5 | C11B—C16B—H16B | 120.0 |
C21—C26—H26 | 120.5 | C15B—C16B—H16B | 120.0 |
| | | |
O2—C1—O1—C11 | 83.0 (3) | O1Ai—C1A—O1A—C11A | 82.6 (3) |
O1—C1—O2—C21 | 85.5 (3) | C1A—O1A—C11A—C12A | −13.4 (5) |
C1—O1—C11—C16 | −147.0 (3) | C1A—O1A—C11A—C16A | 166.0 (3) |
C1—O1—C11—C12 | 37.5 (5) | C16A—C11A—C12A—C13A | −0.8 (5) |
C16—C11—C12—C13 | 0.6 (5) | O1A—C11A—C12A—C13A | 178.5 (3) |
O1—C11—C12—C13 | 176.0 (3) | C11A—C12A—C13A—C14A | 0.1 (5) |
C11—C12—C13—C14 | −0.9 (5) | C12A—C13A—C14A—C15A | 0.7 (5) |
C12—C13—C14—C15 | 0.8 (5) | C12A—C13A—C14A—N1A | −177.5 (3) |
C12—C13—C14—N1 | −175.4 (4) | C13A—C14A—C15A—C16A | −0.8 (5) |
C13—C14—C15—C16 | −0.2 (6) | N1A—C14A—C15A—C16A | 177.4 (3) |
N1—C14—C15—C16 | 175.8 (4) | C14A—C15A—C16A—C11A | 0.1 (5) |
C12—C11—C16—C15 | −0.1 (5) | C12A—C11A—C16A—C15A | 0.7 (5) |
O1—C11—C16—C15 | −175.8 (3) | O1A—C11A—C16A—C15A | −178.7 (3) |
C14—C15—C16—C11 | −0.1 (6) | O1Bii—C1B—O1B—C11B | 80.0 (3) |
C1—O2—C21—C22 | 163.7 (3) | C1B—O1B—C11B—C12B | −146.8 (3) |
C1—O2—C21—C26 | −15.6 (5) | C1B—O1B—C11B—C16B | 39.9 (5) |
C26—C21—C22—C23 | 1.5 (5) | C16B—C11B—C12B—C13B | −0.4 (6) |
O2—C21—C22—C23 | −177.8 (3) | O1B—C11B—C12B—C13B | −174.0 (3) |
C21—C22—C23—C24 | −1.3 (5) | C11B—C12B—C13B—C14B | 0.2 (6) |
C22—C23—C24—C25 | 0.7 (5) | C12B—C13B—C14B—C15B | 0.5 (6) |
C22—C23—C24—N2 | 178.8 (3) | C12B—C13B—C14B—N1B | 174.6 (4) |
C23—C24—C25—C26 | −0.4 (5) | C13B—C14B—C15B—C16B | −0.9 (6) |
N2—C24—C25—C26 | −178.4 (3) | N1B—C14B—C15B—C16B | −175.1 (4) |
C24—C25—C26—C21 | 0.6 (5) | C12B—C11B—C16B—C15B | 0.0 (6) |
C22—C21—C26—C25 | −1.2 (5) | O1B—C11B—C16B—C15B | 173.0 (4) |
O2—C21—C26—C25 | 178.1 (3) | C14B—C15B—C16B—C11B | 0.7 (6) |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N1Biii | 0.92 (3) | 2.31 (2) | 3.158 (5) | 154 (3) |
N1—H1B···O1Aiv | 0.91 (3) | 2.52 (2) | 3.223 (4) | 134 (3) |
N2—H2A···O1Bv | 0.91 (2) | 2.38 (2) | 3.261 (4) | 163 (3) |
N2—H2B···N1A | 0.91 (3) | 2.23 (3) | 3.129 (5) | 167 (3) |
N1A—H1A1···N1vi | 0.92 (3) | 2.31 (3) | 3.208 (5) | 165 (3) |
N1A—H1A2···O2vii | 0.92 (3) | 2.30 (1) | 3.196 (4) | 165 (3) |
N1B—H1B1···N2viii | 0.91 (3) | 2.26 (2) | 3.097 (5) | 152 (3) |
N1B—H1B2···O1vii | 0.90 (3) | 2.48 (2) | 3.285 (4) | 149 (3) |
Symmetry codes: (iii) x, y, z−1; (iv) x+1/2, −y+3/2, z−1/2; (v) x−1/2, −y+3/2, z−1/2; (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. |
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