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The title compound, C
16H
14Br
2N
2O
4, has been synthesized by the reaction of 1,2-bis(aminooxy)ethane with 5-bromo-2-hydroxybenzaldehyde in ethanol. The molecule is centrosymmetric. Intramolecular O—H
N hydrogen bonding is observed between hydroxy groups and oxime N atoms.
Supporting information
CCDC reference: 618968
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.030
- wR factor = 0.083
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.266 0.596
Tmin and Tmax expected: 0.221 0.559
RR = 1.130
Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.10
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.938
Tmax scaled 0.559 Tmin scaled 0.250
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 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
3 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
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
4,4-Dibromo-2,2'-[ethylenedioxybis(nitrilomethylidyne)]diphenol
top
Crystal data top
C16H14Br2N2O4 | F(000) = 452 |
Mr = 458.12 | Dx = 1.812 Mg m−3 |
Monoclinic, P21/c | Melting point = 417.5–418.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 19.249 (3) Å | Cell parameters from 1821 reflections |
b = 5.7607 (8) Å | θ = 3.2–25.0° |
c = 7.620 (1) Å | µ = 4.85 mm−1 |
β = 96.312 (2)° | T = 293 K |
V = 839.82 (19) Å3 | Block, colorless |
Z = 2 | 0.37 × 0.27 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1544 independent reflections |
Radiation source: fine-focus sealed tube | 1297 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −23→17 |
Tmin = 0.266, Tmax = 0.596 | k = −6→6 |
4208 measured reflections | l = −8→9 |
Refinement top
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2088P] where P = (Fo2 + 2Fc2)/3 |
1544 reflections | (Δ/σ)max = 0.001 |
110 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Experimental. 1H NMR (400 MHz, CDCl3): 2.14 (t, J = 6.0 Hz, 2H), 4.48 (s, 4H), 6.87 (d, J
= 8.6 Hz, 2H), 7.26 (d, J = 2.5 Hz, 2H), 7.36 (dd, J = 8.6, 2.5 Hz, 2H), 8.14
(s, 2H), 9.74 (s, 2H). |
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 | |
Br | 0.445844 (15) | 0.81559 (6) | 0.81890 (4) | 0.05050 (16) | |
N | 0.11602 (13) | 0.5986 (5) | 0.6669 (4) | 0.0483 (6) | |
O1 | 0.18335 (14) | 0.2522 (5) | 0.8422 (4) | 0.0624 (7) | |
H1 | 0.1493 | 0.3197 | 0.7921 | 0.094* | |
O2 | 0.06067 (12) | 0.7320 (4) | 0.5817 (4) | 0.0587 (7) | |
C1 | 0.30064 (16) | 0.7249 (5) | 0.7443 (4) | 0.0375 (7) | |
H1A | 0.2998 | 0.8691 | 0.6893 | 0.045* | |
C2 | 0.36323 (15) | 0.6346 (5) | 0.8198 (4) | 0.0373 (6) | |
C3 | 0.36593 (16) | 0.4183 (5) | 0.9004 (4) | 0.0430 (7) | |
H3 | 0.4084 | 0.3578 | 0.9497 | 0.052* | |
C4 | 0.30592 (19) | 0.2955 (5) | 0.9068 (4) | 0.0456 (8) | |
H4 | 0.3077 | 0.1515 | 0.9622 | 0.055* | |
C5 | 0.24158 (17) | 0.3823 (5) | 0.8313 (4) | 0.0417 (7) | |
C6 | 0.23867 (15) | 0.6018 (5) | 0.7499 (4) | 0.0357 (6) | |
C7 | 0.17395 (16) | 0.7045 (5) | 0.6684 (4) | 0.0433 (7) | |
H7 | 0.1750 | 0.8503 | 0.6164 | 0.052* | |
C8 | −0.00196 (16) | 0.5962 (6) | 0.5677 (5) | 0.0570 (9) | |
H8A | −0.0419 | 0.6949 | 0.5324 | 0.068* | |
H8B | −0.0081 | 0.5290 | 0.6817 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.0351 (2) | 0.0563 (2) | 0.0592 (3) | −0.00475 (14) | 0.00105 (15) | 0.00292 (15) |
N | 0.0346 (14) | 0.0497 (15) | 0.0592 (17) | −0.0018 (12) | −0.0010 (12) | −0.0039 (13) |
O1 | 0.0558 (16) | 0.0497 (13) | 0.0806 (19) | −0.0165 (12) | 0.0029 (13) | 0.0113 (13) |
O2 | 0.0358 (13) | 0.0573 (14) | 0.0801 (18) | −0.0019 (11) | −0.0060 (12) | −0.0006 (13) |
C1 | 0.0406 (17) | 0.0338 (14) | 0.0380 (16) | −0.0008 (12) | 0.0041 (13) | −0.0010 (12) |
C2 | 0.0364 (16) | 0.0363 (14) | 0.0391 (16) | −0.0014 (12) | 0.0036 (12) | −0.0058 (12) |
C3 | 0.0460 (18) | 0.0377 (16) | 0.0436 (17) | 0.0076 (14) | −0.0023 (13) | −0.0047 (13) |
C4 | 0.063 (2) | 0.0311 (15) | 0.0426 (18) | 0.0034 (14) | 0.0035 (15) | 0.0025 (12) |
C5 | 0.0471 (18) | 0.0342 (15) | 0.0442 (17) | −0.0104 (13) | 0.0068 (13) | −0.0044 (12) |
C6 | 0.0376 (16) | 0.0326 (14) | 0.0368 (15) | −0.0011 (12) | 0.0035 (12) | −0.0037 (12) |
C7 | 0.0384 (17) | 0.0409 (17) | 0.0502 (18) | −0.0035 (13) | 0.0030 (14) | −0.0042 (13) |
C8 | 0.0309 (16) | 0.069 (2) | 0.071 (2) | −0.0041 (16) | 0.0036 (16) | −0.0098 (19) |
Geometric parameters (Å, º) top
Br—C2 | 1.902 (3) | C3—C4 | 1.360 (5) |
N—C7 | 1.270 (4) | C3—H3 | 0.9300 |
N—O2 | 1.412 (3) | C4—C5 | 1.399 (4) |
O1—C5 | 1.358 (4) | C4—H4 | 0.9300 |
O1—H1 | 0.8200 | C5—C6 | 1.407 (4) |
O2—C8 | 1.431 (4) | C6—C7 | 1.455 (4) |
C1—C2 | 1.378 (4) | C7—H7 | 0.9300 |
C1—C6 | 1.392 (4) | C8—C8i | 1.522 (7) |
C1—H1A | 0.9300 | C8—H8A | 0.9700 |
C2—C3 | 1.388 (4) | C8—H8B | 0.9700 |
| | | |
C7—N—O2 | 111.1 (3) | O1—C5—C4 | 118.5 (3) |
C5—O1—H1 | 109.5 | O1—C5—C6 | 122.0 (3) |
N—O2—C8 | 108.9 (2) | C4—C5—C6 | 119.5 (3) |
C2—C1—C6 | 120.5 (3) | C1—C6—C5 | 118.6 (3) |
C2—C1—H1A | 119.7 | C1—C6—C7 | 118.4 (3) |
C6—C1—H1A | 119.7 | C5—C6—C7 | 123.0 (3) |
C1—C2—C3 | 120.8 (3) | N—C7—C6 | 121.2 (3) |
C1—C2—Br | 119.0 (2) | N—C7—H7 | 119.4 |
C3—C2—Br | 120.2 (2) | C6—C7—H7 | 119.4 |
C4—C3—C2 | 119.5 (3) | O2—C8—C8i | 110.2 (3) |
C4—C3—H3 | 120.3 | O2—C8—H8A | 109.6 |
C2—C3—H3 | 120.3 | C8i—C8—H8A | 109.6 |
C3—C4—C5 | 121.1 (3) | O2—C8—H8B | 109.6 |
C3—C4—H4 | 119.5 | C8i—C8—H8B | 109.6 |
C5—C4—H4 | 119.5 | H8A—C8—H8B | 108.1 |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N | 0.82 | 1.94 | 2.658 (3) | 146 |
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