The molecule of the title compound, C
13H
10Br
2N
2O, is nearly planar and displays a
trans configuration with respect to the central C=N double bond. In the crystal structure, the molecules are linked through intermolecular C—H
Br hydrogen bonds, forming chains running along the
b axis.
Supporting information
CCDC reference: 604967
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.035
- wR factor = 0.075
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N2 .. 3.24 Ang.
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 26.50
From the CIF: _reflns_number_total 2617
Count of symmetry unique reflns 1420
Completeness (_total/calc) 184.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1197
Fraction of Friedel pairs measured 0.843
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.
2,4-Dibromo-6-(4-methylpyridin-2-yliminomethyl)phenol
top
Crystal data top
C13H10Br2N2O | F(000) = 360 |
Mr = 370.05 | Dx = 1.869 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1653 reflections |
a = 6.077 (1) Å | θ = 2.5–24.1° |
b = 14.224 (2) Å | µ = 6.15 mm−1 |
c = 7.676 (1) Å | T = 298 K |
β = 97.791 (2)° | Block, yellow |
V = 657.38 (17) Å3 | 0.20 × 0.20 × 0.19 mm |
Z = 2 | |
Data collection top
Bruker APEX area-detector diffractometer | 2617 independent reflections |
Radiation source: fine-focus sealed tube | 2111 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 26.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −7→7 |
Tmin = 0.298, Tmax = 0.310 | k = −17→17 |
5325 measured reflections | l = −9→9 |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2617 reflections | Δρmax = 0.39 e Å−3 |
166 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: 0.389 (12), 1197 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: Flack (1983) |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 1.35666 (9) | 0.97782 (3) | 0.73700 (8) | 0.06337 (18) | |
Br2 | 1.50915 (10) | 0.58820 (3) | 0.79446 (8) | 0.0678 (2) | |
O1 | 0.9168 (6) | 0.9128 (2) | 0.5442 (5) | 0.0566 (9) | |
H1 | 0.7966 | 0.8941 | 0.4949 | 0.085* | |
N1 | 0.6307 (7) | 0.7910 (3) | 0.3945 (5) | 0.0437 (10) | |
N2 | 0.3830 (7) | 0.6767 (3) | 0.2523 (6) | 0.0570 (12) | |
C1 | 0.9735 (7) | 0.7456 (3) | 0.5627 (6) | 0.0389 (11) | |
C2 | 1.0435 (8) | 0.8395 (3) | 0.5993 (6) | 0.0399 (11) | |
C3 | 1.2516 (8) | 0.8536 (3) | 0.6955 (6) | 0.0408 (11) | |
C4 | 1.3888 (8) | 0.7796 (4) | 0.7537 (6) | 0.0440 (12) | |
H4 | 1.5281 | 0.7906 | 0.8168 | 0.053* | |
C5 | 1.3156 (8) | 0.6884 (3) | 0.7164 (6) | 0.0435 (11) | |
C6 | 1.1133 (8) | 0.6704 (3) | 0.6221 (6) | 0.0432 (11) | |
H6 | 1.0683 | 0.6088 | 0.5974 | 0.052* | |
C7 | 0.7626 (8) | 0.7265 (3) | 0.4553 (6) | 0.0451 (12) | |
H7 | 0.7229 | 0.6643 | 0.4303 | 0.054* | |
C8 | 0.4273 (9) | 0.7670 (3) | 0.2901 (7) | 0.0419 (11) | |
C9 | 0.2835 (8) | 0.8386 (4) | 0.2342 (6) | 0.0454 (11) | |
H9 | 0.3226 | 0.9003 | 0.2647 | 0.054* | |
C10 | 0.0825 (8) | 0.8209 (4) | 0.1335 (7) | 0.0501 (13) | |
C11 | 0.0376 (9) | 0.7271 (4) | 0.0959 (7) | 0.0585 (15) | |
H11 | −0.0964 | 0.7101 | 0.0303 | 0.070* | |
C12 | 0.1885 (9) | 0.6599 (4) | 0.1544 (7) | 0.0622 (15) | |
H12 | 0.1537 | 0.5978 | 0.1241 | 0.075* | |
C13 | −0.0751 (10) | 0.8978 (4) | 0.0703 (8) | 0.0696 (17) | |
H13A | −0.0348 | 0.9541 | 0.1361 | 0.104* | |
H13B | −0.2232 | 0.8797 | 0.0861 | 0.104* | |
H13C | −0.0686 | 0.9093 | −0.0522 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0593 (3) | 0.0380 (3) | 0.0848 (4) | −0.0060 (2) | −0.0192 (3) | −0.0053 (3) |
Br2 | 0.0616 (4) | 0.0452 (3) | 0.0911 (4) | 0.0110 (3) | −0.0095 (3) | 0.0107 (3) |
O1 | 0.046 (2) | 0.0387 (18) | 0.078 (3) | 0.0044 (16) | −0.0163 (18) | −0.0031 (17) |
N1 | 0.038 (2) | 0.045 (2) | 0.048 (3) | −0.0012 (19) | 0.0024 (19) | −0.0029 (19) |
N2 | 0.046 (3) | 0.050 (3) | 0.072 (3) | 0.001 (2) | −0.007 (2) | −0.011 (2) |
C1 | 0.038 (3) | 0.042 (3) | 0.036 (3) | −0.005 (2) | 0.002 (2) | 0.0023 (19) |
C2 | 0.041 (3) | 0.036 (2) | 0.041 (3) | 0.000 (2) | 0.001 (2) | −0.001 (2) |
C3 | 0.042 (3) | 0.031 (3) | 0.047 (3) | −0.004 (2) | 0.000 (2) | −0.007 (2) |
C4 | 0.042 (3) | 0.046 (3) | 0.042 (3) | −0.001 (2) | −0.001 (2) | −0.004 (2) |
C5 | 0.041 (3) | 0.040 (3) | 0.048 (3) | 0.004 (2) | 0.001 (2) | 0.005 (2) |
C6 | 0.050 (3) | 0.031 (3) | 0.048 (3) | −0.003 (2) | 0.005 (2) | 0.000 (2) |
C7 | 0.045 (3) | 0.045 (3) | 0.044 (3) | −0.005 (2) | 0.003 (2) | −0.002 (2) |
C8 | 0.039 (2) | 0.040 (3) | 0.047 (3) | −0.006 (2) | 0.003 (2) | −0.004 (2) |
C9 | 0.042 (3) | 0.042 (3) | 0.051 (3) | −0.005 (2) | 0.001 (2) | 0.003 (2) |
C10 | 0.042 (3) | 0.061 (3) | 0.046 (3) | 0.004 (2) | 0.005 (2) | 0.003 (2) |
C11 | 0.044 (3) | 0.073 (4) | 0.058 (4) | −0.010 (3) | 0.001 (3) | −0.014 (3) |
C12 | 0.054 (3) | 0.052 (3) | 0.076 (4) | −0.005 (3) | −0.008 (3) | −0.016 (3) |
C13 | 0.062 (4) | 0.072 (4) | 0.070 (4) | 0.014 (3) | −0.007 (3) | 0.020 (3) |
Geometric parameters (Å, º) top
Br1—C3 | 1.891 (4) | C5—C6 | 1.364 (6) |
Br2—C5 | 1.893 (5) | C6—H6 | 0.9300 |
O1—C2 | 1.330 (5) | C7—H7 | 0.9300 |
O1—H1 | 0.8200 | C8—C9 | 1.372 (8) |
N1—C7 | 1.265 (6) | C9—C10 | 1.378 (7) |
N1—C8 | 1.420 (6) | C9—H9 | 0.9300 |
N2—C12 | 1.334 (6) | C10—C11 | 1.383 (8) |
N2—C8 | 1.336 (6) | C10—C13 | 1.492 (7) |
C1—C6 | 1.403 (6) | C11—C12 | 1.359 (8) |
C1—C2 | 1.418 (6) | C11—H11 | 0.9300 |
C1—C7 | 1.452 (7) | C12—H12 | 0.9300 |
C2—C3 | 1.390 (6) | C13—H13A | 0.9600 |
C3—C4 | 1.379 (7) | C13—H13B | 0.9600 |
C4—C5 | 1.388 (7) | C13—H13C | 0.9600 |
C4—H4 | 0.9300 | | |
| | | |
C2—O1—H1 | 109.5 | C1—C7—H7 | 118.7 |
C7—N1—C8 | 119.6 (4) | N2—C8—C9 | 123.0 (5) |
C12—N2—C8 | 115.6 (5) | N2—C8—N1 | 119.2 (5) |
C6—C1—C2 | 120.1 (4) | C9—C8—N1 | 117.8 (5) |
C6—C1—C7 | 119.3 (4) | C8—C9—C10 | 121.2 (5) |
C2—C1—C7 | 120.5 (4) | C8—C9—H9 | 119.4 |
O1—C2—C3 | 120.1 (4) | C10—C9—H9 | 119.4 |
O1—C2—C1 | 122.0 (4) | C9—C10—C11 | 115.4 (5) |
C3—C2—C1 | 117.9 (4) | C9—C10—C13 | 122.0 (5) |
C4—C3—C2 | 122.0 (4) | C11—C10—C13 | 122.7 (5) |
C4—C3—Br1 | 118.9 (3) | C12—C11—C10 | 120.3 (5) |
C2—C3—Br1 | 119.1 (3) | C12—C11—H11 | 119.9 |
C3—C4—C5 | 118.9 (4) | C10—C11—H11 | 119.9 |
C3—C4—H4 | 120.6 | N2—C12—C11 | 124.5 (5) |
C5—C4—H4 | 120.6 | N2—C12—H12 | 117.7 |
C6—C5—C4 | 121.7 (4) | C11—C12—H12 | 117.7 |
C6—C5—Br2 | 120.2 (4) | C10—C13—H13A | 109.5 |
C4—C5—Br2 | 118.0 (4) | C10—C13—H13B | 109.5 |
C5—C6—C1 | 119.5 (4) | H13A—C13—H13B | 109.5 |
C5—C6—H6 | 120.3 | C10—C13—H13C | 109.5 |
C1—C6—H6 | 120.3 | H13A—C13—H13C | 109.5 |
N1—C7—C1 | 122.7 (5) | H13B—C13—H13C | 109.5 |
N1—C7—H7 | 118.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Br2i | 0.93 | 2.92 | 3.783 (5) | 155 |
O1—H1···N1 | 0.82 | 1.88 | 2.608 (5) | 147 |
C7—H7···N2 | 0.93 | 2.32 | 2.698 (5) | 104 |
Symmetry code: (i) −x+2, y+1/2, −z+1. |