The molecular structure of (2
E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione (
1) is composed of two
p-chloro phenyl rings, each bonded on opposite ends to a near planar 1,4-
trans enedione moiety [–C(= O)—CH=CH—(C=O)–]. (2
E)-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione (
2) has a similar structure to (
1), but with two
p-bromo phenyl rings and a less planar enedione group. In the crystal, molecules of (
1) exhibit C—Cl

Cl type I interactions, whereas molecules of (
2) present C–Br

Br type II interactions.
Supporting information
CCDC references: 1822698; 1822697
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- Mean
(C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.104
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Datablock: 1
Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 8.218 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.143 Check
Alert level G
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1 ..Cl1 3.38 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 8 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
3 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Datablock: 2
Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.287 Check
Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
2 ALERT level G = General information/check it is not something unexpected
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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009). Software used to prepare material for publication: Mercury (Macrae et al., 2008) for (1); OLEX2 (Dolomanov et al., 2009) for (2).
(2
E)-1,4-Bis(4-chlorophenyl)but-2-ene-1,4-dione (1)
top
Crystal data top
C16H10Cl2O2 | Z = 1 |
Mr = 305.14 | F(000) = 156 |
Triclinic, P1 | Dx = 1.457 Mg m−3 |
a = 3.9455 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.0809 (5) Å | Cell parameters from 2009 reflections |
c = 14.6836 (11) Å | θ = 2.8–26.3° |
α = 82.653 (6)° | µ = 0.46 mm−1 |
β = 88.638 (6)° | T = 298 K |
γ = 84.601 (7)° | Irregular, orange |
V = 347.82 (5) Å3 | 0.34 × 0.22 × 0.15 mm |
Data collection top
Agilent SuperNova, Dualflex, EosS2 diffractometer | 1256 reflections with I > 2σ(I) |
Detector resolution: 8.0945 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 26.4°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlisPro; Bourhis et al., 2015) | h = −4→4 |
Tmin = 0.928, Tmax = 1.000 | k = −7→7 |
5641 measured reflections | l = −18→18 |
1416 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0335P)2 + 0.118P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
1416 reflections | Δρmax = 0.18 e Å−3 |
91 parameters | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.3800 (5) | 0.4949 (3) | 0.30832 (13) | 0.0411 (4) | |
C2 | 0.5146 (5) | 0.2732 (3) | 0.31865 (14) | 0.0482 (5) | |
H2 | 0.493021 | 0.185559 | 0.374837 | 0.058* | |
C3 | 0.6788 (6) | 0.1826 (4) | 0.24675 (15) | 0.0529 (5) | |
H3 | 0.771626 | 0.035173 | 0.254438 | 0.063* | |
C4 | 0.7048 (5) | 0.3111 (4) | 0.16369 (14) | 0.0500 (5) | |
C5 | 0.5749 (6) | 0.5314 (4) | 0.15096 (15) | 0.0559 (6) | |
H5 | 0.595485 | 0.617285 | 0.094315 | 0.067* | |
C6 | 0.4149 (5) | 0.6214 (3) | 0.22341 (14) | 0.0495 (5) | |
H6 | 0.327970 | 0.770037 | 0.215556 | 0.059* | |
C7 | 0.2047 (5) | 0.6004 (3) | 0.38415 (14) | 0.0459 (5) | |
C8 | 0.0820 (5) | 0.4582 (3) | 0.46605 (13) | 0.0452 (5) | |
H8 | 0.123290 | 0.304322 | 0.469025 | 0.054* | |
Cl1 | 0.90353 (18) | 0.19244 (12) | 0.07252 (4) | 0.0768 (3) | |
O1 | 0.1558 (5) | 0.8021 (2) | 0.38003 (11) | 0.0699 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0389 (10) | 0.0429 (10) | 0.0419 (10) | −0.0081 (8) | −0.0005 (8) | −0.0038 (8) |
C2 | 0.0565 (13) | 0.0421 (11) | 0.0450 (11) | −0.0066 (9) | 0.0017 (9) | −0.0003 (9) |
C3 | 0.0558 (13) | 0.0447 (11) | 0.0587 (13) | −0.0013 (10) | −0.0009 (10) | −0.0115 (10) |
C4 | 0.0463 (12) | 0.0595 (13) | 0.0471 (12) | −0.0076 (10) | 0.0021 (9) | −0.0164 (10) |
C5 | 0.0616 (14) | 0.0622 (13) | 0.0413 (11) | −0.0054 (11) | 0.0049 (10) | 0.0017 (10) |
C6 | 0.0539 (12) | 0.0437 (11) | 0.0481 (12) | −0.0008 (9) | 0.0031 (9) | 0.0017 (9) |
C7 | 0.0480 (11) | 0.0440 (11) | 0.0450 (11) | −0.0066 (9) | 0.0022 (9) | −0.0017 (8) |
C8 | 0.0477 (12) | 0.0431 (10) | 0.0440 (11) | −0.0046 (9) | 0.0015 (8) | −0.0023 (8) |
Cl1 | 0.0799 (5) | 0.0926 (5) | 0.0621 (4) | −0.0021 (4) | 0.0148 (3) | −0.0326 (3) |
O1 | 0.1034 (14) | 0.0410 (8) | 0.0617 (10) | −0.0006 (8) | 0.0245 (9) | −0.0015 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.392 (3) | C4—Cl1 | 1.737 (2) |
C1—C6 | 1.390 (3) | C5—H5 | 0.9300 |
C1—C7 | 1.481 (3) | C5—C6 | 1.372 (3) |
C2—H2 | 0.9300 | C6—H6 | 0.9300 |
C2—C3 | 1.374 (3) | C7—C8 | 1.488 (3) |
C3—H3 | 0.9300 | C7—O1 | 1.218 (2) |
C3—C4 | 1.369 (3) | C8—C8i | 1.307 (4) |
C4—C5 | 1.379 (3) | C8—H8 | 0.9300 |
| | | |
C2—C1—C7 | 122.61 (18) | C4—C5—H5 | 120.6 |
C6—C1—C2 | 118.30 (19) | C6—C5—C4 | 118.8 (2) |
C6—C1—C7 | 119.08 (18) | C6—C5—H5 | 120.6 |
C1—C2—H2 | 119.6 | C1—C6—H6 | 119.3 |
C3—C2—C1 | 120.72 (19) | C5—C6—C1 | 121.3 (2) |
C3—C2—H2 | 119.6 | C5—C6—H6 | 119.3 |
C2—C3—H3 | 120.3 | C1—C7—C8 | 119.63 (17) |
C4—C3—C2 | 119.4 (2) | O1—C7—C1 | 120.95 (18) |
C4—C3—H3 | 120.3 | O1—C7—C8 | 119.41 (19) |
C3—C4—C5 | 121.4 (2) | C7—C8—H8 | 118.8 |
C3—C4—Cl1 | 118.98 (17) | C8i—C8—C7 | 122.3 (2) |
C5—C4—Cl1 | 119.60 (17) | C8i—C8—H8 | 118.8 |
| | | |
C1—C2—C3—C4 | −1.1 (3) | C4—C5—C6—C1 | −0.4 (3) |
C1—C7—C8—C8i | −178.2 (2) | C6—C1—C2—C3 | 0.3 (3) |
C2—C1—C6—C5 | 0.5 (3) | C6—C1—C7—C8 | 163.48 (18) |
C2—C1—C7—C8 | −17.0 (3) | C6—C1—C7—O1 | −15.6 (3) |
C2—C1—C7—O1 | 163.9 (2) | C7—C1—C2—C3 | −179.24 (19) |
C2—C3—C4—C5 | 1.2 (3) | C7—C1—C6—C5 | −179.94 (19) |
C2—C3—C4—Cl1 | −178.37 (16) | Cl1—C4—C5—C6 | 179.15 (16) |
C3—C4—C5—C6 | −0.4 (3) | O1—C7—C8—C8i | 0.9 (4) |
Symmetry code: (i) −x, −y+1, −z+1. |
(2
E)-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione (2)
top
Crystal data top
C16H10Br2O2 | F(000) = 384 |
Mr = 394.06 | Dx = 1.800 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.4391 (7) Å | Cell parameters from 2527 reflections |
b = 3.9937 (2) Å | θ = 2.9–26.2° |
c = 12.7244 (7) Å | µ = 5.57 mm−1 |
β = 97.827 (5)° | T = 298 K |
V = 726.92 (7) Å3 | Irregular, yellow |
Z = 2 | 0.35 × 0.14 × 0.12 mm |
Data collection top
Agilent SuperNova, Dualflex, EosS2 diffractometer | 1228 reflections with I > 2σ(I) |
Detector resolution: 8.0945 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlisPro; Bourhis et al., 2015) | h = −18→18 |
Tmin = 0.370, Tmax = 1.000 | k = −4→4 |
6231 measured reflections | l = −15→15 |
1470 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0234P)2 + 0.4382P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.36 e Å−3 |
1470 reflections | Δρmin = −0.43 e Å−3 |
92 parameters | Extinction correction: SHELXL-2016/4 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0047 (8) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.06905 (2) | 0.86344 (8) | 0.66837 (3) | 0.05337 (16) | |
C1 | 0.31059 (19) | 0.3876 (7) | 0.5110 (2) | 0.0355 (6) | |
C2 | 0.3212 (2) | 0.4543 (8) | 0.6188 (2) | 0.0444 (7) | |
H2 | 0.377230 | 0.400535 | 0.660470 | 0.053* | |
C3 | 0.2503 (2) | 0.5990 (8) | 0.6653 (2) | 0.0471 (8) | |
H3 | 0.258517 | 0.646056 | 0.737543 | 0.057* | |
C4 | 0.1673 (2) | 0.6726 (6) | 0.6034 (2) | 0.0391 (7) | |
C5 | 0.1538 (2) | 0.6073 (7) | 0.4962 (2) | 0.0463 (7) | |
H5 | 0.097052 | 0.657253 | 0.455312 | 0.056* | |
C6 | 0.2258 (2) | 0.4666 (8) | 0.4507 (2) | 0.0422 (7) | |
H6 | 0.217497 | 0.423632 | 0.378154 | 0.051* | |
C7 | 0.3859 (2) | 0.2399 (8) | 0.4570 (2) | 0.0418 (7) | |
C8 | 0.4672 (2) | 0.0760 (7) | 0.5218 (2) | 0.0410 (7) | |
H8 | 0.471561 | 0.081856 | 0.595399 | 0.049* | |
O1 | 0.38162 (17) | 0.2478 (7) | 0.36132 (17) | 0.0665 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0433 (2) | 0.0504 (2) | 0.0706 (3) | 0.00725 (15) | 0.02309 (16) | 0.00106 (17) |
C1 | 0.0354 (15) | 0.0380 (14) | 0.0334 (15) | −0.0010 (12) | 0.0057 (12) | 0.0011 (12) |
C2 | 0.0380 (17) | 0.0601 (19) | 0.0340 (16) | 0.0088 (14) | 0.0012 (13) | −0.0001 (14) |
C3 | 0.0465 (18) | 0.0598 (19) | 0.0359 (16) | 0.0119 (15) | 0.0082 (13) | −0.0026 (15) |
C4 | 0.0371 (16) | 0.0344 (15) | 0.0487 (18) | 0.0009 (12) | 0.0158 (13) | 0.0028 (13) |
C5 | 0.0371 (16) | 0.0514 (18) | 0.0487 (18) | 0.0054 (14) | 0.0002 (13) | 0.0034 (15) |
C6 | 0.0439 (17) | 0.0491 (17) | 0.0328 (15) | 0.0031 (14) | 0.0030 (13) | −0.0006 (13) |
C7 | 0.0395 (16) | 0.0480 (16) | 0.0382 (17) | −0.0016 (13) | 0.0060 (13) | −0.0057 (13) |
C8 | 0.0364 (16) | 0.0514 (18) | 0.0357 (15) | −0.0005 (13) | 0.0060 (12) | −0.0064 (14) |
O1 | 0.0591 (15) | 0.109 (2) | 0.0322 (12) | 0.0232 (14) | 0.0078 (11) | −0.0071 (12) |
Geometric parameters (Å, º) top
Br1—C4 | 1.896 (3) | C4—C5 | 1.376 (4) |
C1—C2 | 1.385 (4) | C5—H5 | 0.9300 |
C1—C6 | 1.390 (4) | C5—C6 | 1.377 (4) |
C1—C7 | 1.485 (4) | C6—H6 | 0.9300 |
C2—H2 | 0.9300 | C7—C8 | 1.492 (4) |
C2—C3 | 1.378 (4) | C7—O1 | 1.211 (3) |
C3—H3 | 0.9300 | C8—C8i | 1.310 (5) |
C3—C4 | 1.374 (4) | C8—H8 | 0.9300 |
| | | |
C2—C1—C6 | 118.3 (3) | C4—C5—H5 | 120.6 |
C2—C1—C7 | 123.1 (3) | C4—C5—C6 | 118.8 (3) |
C6—C1—C7 | 118.7 (3) | C6—C5—H5 | 120.6 |
C1—C2—H2 | 119.4 | C1—C6—H6 | 119.4 |
C3—C2—C1 | 121.2 (3) | C5—C6—C1 | 121.3 (3) |
C3—C2—H2 | 119.4 | C5—C6—H6 | 119.4 |
C2—C3—H3 | 120.5 | C1—C7—C8 | 119.3 (2) |
C4—C3—C2 | 119.0 (3) | O1—C7—C1 | 121.0 (3) |
C4—C3—H3 | 120.5 | O1—C7—C8 | 119.7 (3) |
C3—C4—Br1 | 118.8 (2) | C7—C8—H8 | 119.0 |
C3—C4—C5 | 121.5 (3) | C8i—C8—C7 | 121.9 (4) |
C5—C4—Br1 | 119.7 (2) | C8i—C8—H8 | 119.0 |
| | | |
Br1—C4—C5—C6 | −179.6 (2) | C3—C4—C5—C6 | −0.4 (5) |
C1—C2—C3—C4 | 1.0 (5) | C4—C5—C6—C1 | 0.6 (5) |
C1—C7—C8—C8i | 175.8 (3) | C6—C1—C2—C3 | −0.8 (5) |
C2—C1—C6—C5 | −0.1 (4) | C6—C1—C7—C8 | −164.8 (3) |
C2—C1—C7—C8 | 16.0 (4) | C6—C1—C7—O1 | 14.5 (4) |
C2—C1—C7—O1 | −164.7 (3) | C7—C1—C2—C3 | 178.4 (3) |
C2—C3—C4—Br1 | 178.8 (2) | C7—C1—C6—C5 | −179.3 (3) |
C2—C3—C4—C5 | −0.5 (5) | O1—C7—C8—C8i | −3.5 (6) |
Symmetry code: (i) −x+1, −y, −z+1. |