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The crystal structure of the title compound, C16H17NO2, contains two independent mol­ecules in the asymmetric unit. Both mol­ecules adopt the phenol–imine tautomeric form, with strong intra­molecular O—H...N hydrogen bonds. The crystal packing is stabilized by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002322/kp2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002322/kp2076Isup2.hkl
Contains datablock I

CCDC reference: 636728

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for O1B - C1B .. 6.55 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O2B - C12B .. 5.12 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2B - C3B .. 6.22 su PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1A - H1A ... 1.06 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-2-[1-(4-Ethoxyphenylimino)ethyl]phenol top
Crystal data top
C16H17NO2Z = 4
Mr = 255.31F(000) = 544
Triclinic, P1Dx = 1.229 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0671 (7) ÅCell parameters from 21129 reflections
b = 11.1923 (8) Åθ = 1.9–27.9°
c = 14.8312 (12) ŵ = 0.08 mm1
α = 86.037 (6)°T = 296 K
β = 75.742 (6)°Prism, green
γ = 71.119 (6)°0.75 × 0.60 × 0.36 mm
V = 1380.15 (18) Å3
Data collection top
Stoe IPDS-2
diffractometer
3807 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 27.9°, θmin = 1.9°
Detector resolution: 6.67 pixels mm-1h = 1111
ω scansk = 1414
22614 measured reflectionsl = 1919
6540 independent reflections
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)] = 0.038All H-atom parameters refined
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0589P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
6540 reflectionsΔρmax = 0.12 e Å3
480 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0189 (17)
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.

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
H2A0.7904 (19)0.8443 (16)0.4806 (11)0.099 (5)*
H2B1.3045 (18)0.3804 (15)0.4939 (11)0.095 (5)*
H3A0.8555 (18)1.0344 (15)0.4892 (11)0.095 (5)*
H3B1.3709 (18)0.5698 (14)0.4975 (11)0.096 (5)*
H4A0.7574 (19)1.2111 (16)0.4087 (11)0.103 (5)*
H4B1.2644 (18)0.7444 (15)0.4055 (10)0.101 (5)*
H5A0.5728 (18)1.2108 (15)0.3200 (11)0.090 (5)*
H5B1.0895 (16)0.7261 (13)0.3181 (10)0.078 (4)*
H8A0.358 (2)1.1228 (15)0.1874 (12)0.102 (5)*
H8B0.502 (2)1.1648 (15)0.1974 (11)0.099 (5)*
H8C0.337 (2)1.2112 (19)0.2716 (13)0.126 (6)*
H8D0.8794 (19)0.6211 (14)0.1898 (11)0.096 (5)*
H8E1.027 (2)0.6654 (15)0.1933 (12)0.103 (5)*
H8F0.857 (2)0.7144 (19)0.2691 (13)0.128 (7)*
H10A0.1156 (15)1.0494 (12)0.3100 (9)0.071 (4)*
H10B0.6353 (17)0.5516 (14)0.3217 (10)0.089 (4)*
H11A0.0606 (18)1.0245 (13)0.2259 (10)0.082 (4)*
H11B0.4634 (18)0.5206 (13)0.2401 (10)0.082 (4)*
H13A0.3051 (15)0.7639 (13)0.0595 (9)0.074 (4)*
H13B0.8308 (14)0.2598 (11)0.0755 (8)0.062 (3)*
H14A0.4783 (16)0.7836 (12)0.1511 (9)0.071 (4)*
H14B1.0061 (17)0.2854 (13)0.1616 (9)0.081 (4)*
H15A0.1653 (17)1.0304 (15)0.0909 (10)0.087 (4)*
H15B0.1970 (16)0.9262 (12)0.1684 (10)0.075 (4)*
H15C0.3615 (17)0.5268 (15)0.1056 (10)0.083 (4)*
H15D0.3199 (16)0.4228 (13)0.1819 (10)0.079 (4)*
H16A0.341 (2)0.9391 (17)0.0483 (12)0.115 (6)*
H16B0.176 (2)0.9032 (16)0.0278 (13)0.115 (6)*
H16C0.2081 (18)0.7985 (17)0.0522 (11)0.098 (5)*
H16D0.187 (2)0.4433 (16)0.0552 (11)0.100 (5)*
H16E0.350 (2)0.4070 (15)0.0156 (13)0.104 (5)*
H16F0.311 (2)0.3030 (19)0.0581 (12)0.118 (6)*
H1B1.0495 (18)0.3449 (14)0.3720 (11)0.085 (4)*
H1A0.521 (2)0.8364 (19)0.3514 (15)0.143 (7)*
C1B1.16040 (14)0.44268 (11)0.40599 (8)0.0613 (3)
C2B1.26215 (16)0.45331 (16)0.45952 (9)0.0746 (4)
C3B1.29759 (17)0.56272 (15)0.46043 (10)0.0764 (4)
C4B1.23491 (17)0.66418 (15)0.40787 (9)0.0740 (4)
C5B1.13546 (16)0.65491 (13)0.35417 (9)0.0657 (3)
C6B1.09475 (13)0.54507 (10)0.35122 (7)0.0563 (3)
C7B0.98714 (14)0.53698 (11)0.29395 (7)0.0563 (3)
C8B0.9338 (2)0.64415 (14)0.23072 (11)0.0715 (4)
C9B0.83832 (15)0.42267 (10)0.24826 (8)0.0585 (3)
C10B0.67692 (16)0.49069 (12)0.27113 (9)0.0670 (3)
C11B0.57243 (16)0.47470 (12)0.22286 (9)0.0652 (3)
C12B0.63044 (14)0.38970 (10)0.14890 (8)0.0569 (3)
C13B0.79149 (15)0.31911 (12)0.12659 (9)0.0654 (3)
C14B0.89343 (16)0.33405 (12)0.17632 (9)0.0648 (3)
C15B0.37284 (16)0.43978 (14)0.11359 (10)0.0685 (3)
C16B0.3005 (2)0.39662 (19)0.04737 (12)0.0828 (4)
N1B0.94658 (12)0.43604 (9)0.29865 (7)0.0622 (3)
O1B1.12686 (13)0.33383 (9)0.40821 (7)0.0784 (3)
O2B0.53865 (10)0.36826 (8)0.09481 (6)0.0670 (2)
C1A0.64082 (14)0.92035 (12)0.39641 (8)0.0658 (3)
C2A0.74621 (18)0.92312 (17)0.44941 (10)0.0815 (4)
C3A0.78574 (19)1.03024 (19)0.45434 (11)0.0870 (5)
C4A0.7233 (2)1.13701 (18)0.40628 (11)0.0855 (4)
C5A0.62006 (18)1.13547 (14)0.35339 (9)0.0732 (4)
C6A0.57551 (14)1.02804 (11)0.34612 (8)0.0603 (3)
C7A0.46547 (14)1.02769 (11)0.28830 (8)0.0598 (3)
C8A0.4116 (2)1.14056 (14)0.22978 (12)0.0771 (4)
C9A0.31483 (15)0.91974 (11)0.23646 (8)0.0618 (3)
C10A0.15394 (16)0.98938 (13)0.25888 (9)0.0697 (3)
C11A0.04917 (17)0.97574 (12)0.20981 (9)0.0667 (3)
C12A0.10610 (15)0.89148 (11)0.13539 (8)0.0597 (3)
C13A0.26711 (16)0.81988 (12)0.11318 (9)0.0655 (3)
C14A0.36912 (17)0.83258 (12)0.16340 (9)0.0671 (3)
C15A0.15278 (16)0.93918 (14)0.10204 (10)0.0706 (3)
C16A0.2261 (2)0.89048 (19)0.03906 (13)0.0857 (4)
N1A0.42293 (12)0.92839 (9)0.28831 (7)0.0651 (3)
O1A0.60472 (12)0.81298 (9)0.39403 (7)0.0834 (3)
O2A0.01439 (10)0.87113 (8)0.08118 (6)0.0682 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1B0.0603 (7)0.0615 (7)0.0529 (6)0.0120 (6)0.0069 (5)0.0010 (5)
C2B0.0665 (8)0.0862 (10)0.0605 (7)0.0085 (7)0.0176 (6)0.0033 (7)
C3B0.0674 (8)0.0967 (11)0.0642 (8)0.0218 (8)0.0168 (7)0.0088 (7)
C4B0.0760 (9)0.0825 (9)0.0660 (8)0.0296 (7)0.0127 (7)0.0088 (7)
C5B0.0711 (8)0.0670 (8)0.0569 (7)0.0211 (6)0.0120 (6)0.0002 (6)
C6B0.0558 (6)0.0602 (7)0.0453 (5)0.0129 (5)0.0055 (5)0.0007 (5)
C7B0.0589 (7)0.0561 (6)0.0468 (6)0.0147 (5)0.0045 (5)0.0004 (5)
C8B0.0816 (10)0.0684 (8)0.0695 (8)0.0270 (8)0.0269 (8)0.0161 (7)
C9B0.0664 (7)0.0532 (6)0.0539 (6)0.0202 (6)0.0100 (5)0.0042 (5)
C10B0.0686 (8)0.0688 (8)0.0581 (7)0.0182 (7)0.0063 (6)0.0120 (6)
C11B0.0593 (7)0.0664 (7)0.0621 (7)0.0148 (6)0.0044 (6)0.0106 (6)
C12B0.0634 (7)0.0540 (6)0.0539 (6)0.0241 (6)0.0077 (5)0.0002 (5)
C13B0.0662 (8)0.0569 (7)0.0673 (7)0.0175 (6)0.0040 (6)0.0134 (6)
C14B0.0599 (7)0.0568 (7)0.0715 (8)0.0140 (6)0.0087 (6)0.0061 (6)
C15B0.0655 (8)0.0633 (8)0.0756 (9)0.0213 (7)0.0135 (7)0.0010 (6)
C16B0.0799 (11)0.0954 (12)0.0800 (10)0.0358 (9)0.0221 (8)0.0063 (8)
N1B0.0686 (6)0.0613 (6)0.0564 (5)0.0205 (5)0.0150 (5)0.0035 (4)
O1B0.0873 (7)0.0662 (6)0.0816 (6)0.0191 (5)0.0313 (5)0.0161 (5)
O2B0.0638 (5)0.0685 (5)0.0671 (5)0.0213 (4)0.0091 (4)0.0107 (4)
C1A0.0577 (7)0.0694 (8)0.0562 (7)0.0101 (6)0.0025 (6)0.0036 (6)
C2A0.0682 (9)0.0967 (11)0.0650 (8)0.0110 (8)0.0116 (7)0.0077 (8)
C3A0.0712 (9)0.1206 (14)0.0659 (8)0.0244 (9)0.0141 (7)0.0139 (9)
C4A0.0884 (10)0.0966 (11)0.0728 (9)0.0324 (9)0.0115 (8)0.0211 (8)
C5A0.0824 (9)0.0698 (8)0.0616 (7)0.0198 (7)0.0100 (7)0.0085 (6)
C6A0.0606 (7)0.0622 (7)0.0483 (6)0.0136 (6)0.0018 (5)0.0035 (5)
C7A0.0630 (7)0.0553 (6)0.0504 (6)0.0131 (5)0.0015 (5)0.0008 (5)
C8A0.0904 (11)0.0643 (8)0.0798 (9)0.0262 (8)0.0274 (9)0.0146 (7)
C9A0.0675 (8)0.0565 (7)0.0590 (6)0.0224 (6)0.0086 (6)0.0056 (5)
C10A0.0710 (8)0.0694 (8)0.0611 (7)0.0180 (7)0.0039 (6)0.0124 (6)
C11A0.0612 (8)0.0661 (8)0.0623 (7)0.0135 (6)0.0020 (6)0.0079 (6)
C12A0.0657 (7)0.0548 (6)0.0540 (6)0.0219 (6)0.0023 (5)0.0014 (5)
C13A0.0722 (8)0.0567 (7)0.0608 (7)0.0193 (6)0.0031 (6)0.0069 (5)
C14A0.0633 (8)0.0569 (7)0.0707 (8)0.0141 (6)0.0028 (6)0.0031 (6)
C15A0.0683 (8)0.0698 (8)0.0683 (8)0.0222 (7)0.0062 (7)0.0007 (6)
C16A0.0873 (12)0.0920 (12)0.0859 (11)0.0392 (10)0.0219 (9)0.0061 (9)
N1A0.0705 (6)0.0592 (6)0.0623 (6)0.0198 (5)0.0123 (5)0.0065 (5)
O1A0.0850 (7)0.0699 (6)0.0903 (7)0.0201 (5)0.0238 (6)0.0230 (5)
O2A0.0698 (5)0.0692 (5)0.0623 (5)0.0225 (4)0.0068 (4)0.0070 (4)
Geometric parameters (Å, º) top
C1B—O1B1.3443 (15)C1A—O1A1.3486 (16)
C1B—C2B1.3931 (18)C1A—C2A1.387 (2)
C1B—C6B1.4126 (16)C1A—C6A1.4111 (17)
C2B—C3B1.364 (2)C2A—C3A1.369 (2)
C2B—H2B0.954 (17)C2A—H2A0.979 (17)
C3B—C4B1.378 (2)C3A—C4A1.378 (2)
C3B—H3B0.986 (16)C3A—H3A0.924 (16)
C4B—C5B1.3726 (19)C4A—C5A1.366 (2)
C4B—H4B1.012 (16)C4A—H4A0.980 (17)
C5B—C6B1.3994 (17)C5A—C6A1.4051 (18)
C5B—H5B0.965 (15)C5A—H5A0.976 (16)
C6B—C7B1.4689 (16)C6A—C7A1.4681 (17)
C7B—N1B1.2891 (14)C7A—N1A1.2889 (15)
C7B—C8B1.4984 (17)C7A—C8A1.4985 (18)
C8B—H8D0.963 (17)C8A—H8A0.952 (17)
C8B—H8E0.979 (18)C8A—H8B0.954 (17)
C8B—H8F0.97 (2)C8A—H8C0.99 (2)
C9B—C10B1.3807 (17)C9A—C10A1.3811 (17)
C9B—C14B1.3909 (16)C9A—C14A1.3930 (17)
C9B—N1B1.4200 (15)C9A—N1A1.4157 (16)
C10B—C11B1.3797 (18)C10A—C11A1.3803 (19)
C10B—H10B0.967 (14)C10A—H10A0.967 (13)
C11B—C12B1.3861 (15)C11A—C12A1.3864 (16)
C11B—H11B0.934 (15)C11A—H11A0.946 (14)
C12B—O2B1.3706 (14)C12A—O2A1.3665 (15)
C12B—C13B1.3847 (17)C12A—C13A1.3872 (17)
C13B—C14B1.3709 (18)C13A—C14A1.3673 (19)
C13B—H13B0.961 (12)C13A—H13A0.969 (13)
C14B—H14B0.967 (14)C14A—H14A0.942 (13)
C15B—O2B1.4228 (15)C15A—O2A1.4240 (16)
C15B—C16B1.489 (2)C15A—C16A1.491 (2)
C15B—H15C0.948 (15)C15A—H15A0.997 (15)
C15B—H15D1.042 (14)C15A—H15B0.987 (14)
C16B—H16D0.972 (18)C16A—H16A0.984 (19)
C16B—H16E0.949 (18)C16A—H16B1.005 (19)
C16B—H16F1.026 (19)C16A—H16C1.001 (17)
O1B—H1B0.957 (16)O1A—H1A1.06 (2)
O1B—C1B—C2B118.50 (12)O1A—C1A—C2A118.40 (13)
O1B—C1B—C6B121.52 (11)O1A—C1A—C6A121.75 (12)
C2B—C1B—C6B119.98 (12)C2A—C1A—C6A119.84 (14)
C3B—C2B—C1B120.47 (14)C3A—C2A—C1A120.48 (16)
C3B—C2B—H2B123.5 (9)C3A—C2A—H2A123.8 (9)
C1B—C2B—H2B116.0 (9)C1A—C2A—H2A115.7 (9)
C2B—C3B—C4B120.77 (14)C2A—C3A—C4A120.95 (16)
C2B—C3B—H3B120.5 (9)C2A—C3A—H3A122.1 (10)
C4B—C3B—H3B118.7 (9)C4A—C3A—H3A117.0 (10)
C5B—C4B—C3B119.49 (14)C5A—C4A—C3A119.23 (16)
C5B—C4B—H4B118.9 (9)C5A—C4A—H4A121.4 (10)
C3B—C4B—H4B121.6 (9)C3A—C4A—H4A119.3 (10)
C4B—C5B—C6B121.95 (14)C4A—C5A—C6A122.04 (15)
C4B—C5B—H5B120.0 (8)C4A—C5A—H5A120.3 (9)
C6B—C5B—H5B118.1 (8)C6A—C5A—H5A117.6 (9)
C5B—C6B—C1B117.34 (12)C5A—C6A—C1A117.45 (12)
C5B—C6B—C7B121.29 (11)C5A—C6A—C7A121.31 (12)
C1B—C6B—C7B121.37 (11)C1A—C6A—C7A121.24 (11)
N1B—C7B—C6B118.22 (10)N1A—C7A—C6A118.25 (11)
N1B—C7B—C8B123.03 (11)N1A—C7A—C8A122.89 (13)
C6B—C7B—C8B118.72 (11)C6A—C7A—C8A118.83 (12)
C7B—C8B—H8D110.2 (9)C7A—C8A—H8A110.6 (10)
C7B—C8B—H8E109.8 (10)C7A—C8A—H8B109.5 (10)
H8D—C8B—H8E109.1 (13)H8A—C8A—H8B110.9 (14)
C7B—C8B—H8F107.7 (12)C7A—C8A—H8C108.3 (11)
H8D—C8B—H8F107.3 (14)H8A—C8A—H8C109.0 (14)
H8E—C8B—H8F112.6 (15)H8B—C8A—H8C108.5 (15)
C10B—C9B—C14B118.24 (12)C10A—C9A—C14A118.07 (12)
C10B—C9B—N1B122.12 (10)C10A—C9A—N1A122.47 (11)
C14B—C9B—N1B119.56 (11)C14A—C9A—N1A119.35 (11)
C11B—C10B—C9B121.51 (11)C11A—C10A—C9A121.58 (12)
C11B—C10B—H10B118.7 (9)C11A—C10A—H10A120.1 (8)
C9B—C10B—H10B119.8 (9)C9A—C10A—H10A118.3 (8)
C10B—C11B—C12B119.52 (12)C10A—C11A—C12A119.63 (12)
C10B—C11B—H11B120.2 (8)C10A—C11A—H11A120.4 (8)
C12B—C11B—H11B120.3 (8)C12A—C11A—H11A119.9 (8)
O2B—C12B—C13B116.01 (10)O2A—C12A—C11A124.84 (11)
O2B—C12B—C11B124.57 (11)O2A—C12A—C13A115.98 (10)
C13B—C12B—C11B119.42 (12)C11A—C12A—C13A119.18 (12)
C14B—C13B—C12B120.45 (11)C14A—C13A—C12A120.63 (11)
C14B—C13B—H13B120.5 (7)C14A—C13A—H13A121.6 (8)
C12B—C13B—H13B119.0 (7)C12A—C13A—H13A117.8 (8)
C13B—C14B—C9B120.77 (12)C13A—C14A—C9A120.87 (13)
C13B—C14B—H14B121.4 (8)C13A—C14A—H14A122.5 (8)
C9B—C14B—H14B117.8 (8)C9A—C14A—H14A116.6 (8)
O2B—C15B—C16B107.75 (12)O2A—C15A—C16A107.67 (13)
O2B—C15B—H15C109.5 (9)O2A—C15A—H15A107.9 (8)
C16B—C15B—H15C110.6 (9)C16A—C15A—H15A111.0 (8)
O2B—C15B—H15D108.2 (8)O2A—C15A—H15B107.6 (8)
C16B—C15B—H15D110.5 (7)C16A—C15A—H15B112.7 (7)
H15C—C15B—H15D110.3 (11)H15A—C15A—H15B109.8 (11)
C15B—C16B—H16D112.3 (10)C15A—C16A—H16A110.3 (10)
C15B—C16B—H16E112.4 (10)C15A—C16A—H16B110.6 (10)
H16D—C16B—H16E106.0 (14)H16A—C16A—H16B105.3 (15)
C15B—C16B—H16F109.5 (10)C15A—C16A—H16C107.6 (9)
H16D—C16B—H16F107.8 (14)H16A—C16A—H16C112.4 (14)
H16E—C16B—H16F108.6 (14)H16B—C16A—H16C110.6 (13)
C7B—N1B—C9B121.74 (10)C7A—N1A—C9A122.57 (10)
C1B—O1B—H1B107.6 (9)C1A—O1A—H1A103.4 (11)
C12B—O2B—C15B118.41 (9)C12A—O2A—C15A118.71 (9)
O1B—C1B—C2B—C3B179.04 (12)O1A—C1A—C2A—C3A179.64 (12)
C6B—C1B—C2B—C3B0.81 (18)C6A—C1A—C2A—C3A0.90 (19)
C1B—C2B—C3B—C4B0.6 (2)C1A—C2A—C3A—C4A0.6 (2)
C2B—C3B—C4B—C5B0.1 (2)C2A—C3A—C4A—C5A0.3 (2)
C3B—C4B—C5B—C6B0.23 (19)C3A—C4A—C5A—C6A0.2 (2)
C4B—C5B—C6B—C1B0.06 (17)C4A—C5A—C6A—C1A0.44 (18)
C4B—C5B—C6B—C7B179.52 (11)C4A—C5A—C6A—C7A179.46 (12)
O1B—C1B—C6B—C5B179.39 (10)O1A—C1A—C6A—C5A179.78 (11)
C2B—C1B—C6B—C5B0.45 (16)C2A—C1A—C6A—C5A0.79 (17)
O1B—C1B—C6B—C7B0.19 (16)O1A—C1A—C6A—C7A0.32 (17)
C2B—C1B—C6B—C7B179.97 (10)C2A—C1A—C6A—C7A179.11 (11)
C5B—C6B—C7B—N1B175.84 (10)C5A—C6A—C7A—N1A176.52 (11)
C1B—C6B—C7B—N1B3.72 (15)C1A—C6A—C7A—N1A3.58 (16)
C5B—C6B—C7B—C8B6.05 (16)C5A—C6A—C7A—C8A5.36 (17)
C1B—C6B—C7B—C8B174.39 (12)C1A—C6A—C7A—C8A174.54 (12)
C14B—C9B—C10B—C11B1.76 (19)C14A—C9A—C10A—C11A1.22 (19)
N1B—C9B—C10B—C11B178.53 (12)N1A—C9A—C10A—C11A177.26 (12)
C9B—C10B—C11B—C12B0.8 (2)C9A—C10A—C11A—C12A0.8 (2)
C10B—C11B—C12B—O2B178.45 (11)C10A—C11A—C12A—O2A179.20 (11)
C10B—C11B—C12B—C13B2.13 (19)C10A—C11A—C12A—C13A1.67 (18)
O2B—C12B—C13B—C14B179.72 (11)O2A—C12A—C13A—C14A179.69 (11)
C11B—C12B—C13B—C14B0.81 (19)C11A—C12A—C13A—C14A0.49 (18)
C12B—C13B—C14B—C9B1.84 (19)C12A—C13A—C14A—C9A1.60 (19)
C10B—C9B—C14B—C13B3.09 (18)C10A—C9A—C14A—C13A2.42 (18)
N1B—C9B—C14B—C13B179.95 (11)N1A—C9A—C14A—C13A178.60 (11)
C6B—C7B—N1B—C9B177.59 (10)C6A—C7A—N1A—C9A178.67 (10)
C8B—C7B—N1B—C9B4.38 (17)C8A—C7A—N1A—C9A3.30 (18)
C10B—C9B—N1B—C7B70.37 (15)C10A—C9A—N1A—C7A69.29 (16)
C14B—C9B—N1B—C7B112.89 (13)C14A—C9A—N1A—C7A114.72 (13)
C13B—C12B—O2B—C15B178.92 (11)C11A—C12A—O2A—C15A0.87 (17)
C11B—C12B—O2B—C15B1.64 (17)C13A—C12A—O2A—C15A178.29 (11)
C16B—C15B—O2B—C12B178.64 (11)C16A—C15A—O2A—C12A174.56 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···N1B0.957 (16)1.681 (16)2.5420 (14)147.7 (13)
O1A—H1A···N1A1.06 (2)1.55 (2)2.5415 (14)152.3 (18)
 

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