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The mol­ecular structure of (2E)-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)–]. (2E)-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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901800230X/zl2724sup1.cif
Contains datablocks 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800230X/zl27241sup4.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901800230X/zl27242sup5.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800230X/zl27241sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901800230X/zl27242sup5.cml
Supplementary material

CCDC references: 1822698; 1822697

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](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

Computing details top

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).

(2E)-1,4-Bis(4-chlorophenyl)but-2-ene-1,4-dione (1) top
Crystal data top
C16H10Cl2O2Z = 1
Mr = 305.14F(000) = 156
Triclinic, P1Dx = 1.457 Mg m3
a = 3.9455 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.0809 (5) ÅCell parameters from 2009 reflections
c = 14.6836 (11) Åθ = 2.8–26.3°
α = 82.653 (6)°µ = 0.46 mm1
β = 88.638 (6)°T = 298 K
γ = 84.601 (7)°Irregular, orange
V = 347.82 (5) Å30.34 × 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-1Rint = 0.023
ω scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlisPro; Bourhis et al., 2015)
h = 44
Tmin = 0.928, Tmax = 1.000k = 77
5641 measured reflectionsl = 1818
1416 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.18 e Å3
91 parametersΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
C10.3800 (5)0.4949 (3)0.30832 (13)0.0411 (4)
C20.5146 (5)0.2732 (3)0.31865 (14)0.0482 (5)
H20.4930210.1855590.3748370.058*
C30.6788 (6)0.1826 (4)0.24675 (15)0.0529 (5)
H30.7716260.0351730.2544380.063*
C40.7048 (5)0.3111 (4)0.16369 (14)0.0500 (5)
C50.5749 (6)0.5314 (4)0.15096 (15)0.0559 (6)
H50.5954850.6172850.0943150.067*
C60.4149 (5)0.6214 (3)0.22341 (14)0.0495 (5)
H60.3279700.7700370.2155560.059*
C70.2047 (5)0.6004 (3)0.38415 (14)0.0459 (5)
C80.0820 (5)0.4582 (3)0.46605 (13)0.0452 (5)
H80.1232900.3043220.4690250.054*
Cl10.90353 (18)0.19244 (12)0.07252 (4)0.0768 (3)
O10.1558 (5)0.8021 (2)0.38003 (11)0.0699 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0389 (10)0.0429 (10)0.0419 (10)0.0081 (8)0.0005 (8)0.0038 (8)
C20.0565 (13)0.0421 (11)0.0450 (11)0.0066 (9)0.0017 (9)0.0003 (9)
C30.0558 (13)0.0447 (11)0.0587 (13)0.0013 (10)0.0009 (10)0.0115 (10)
C40.0463 (12)0.0595 (13)0.0471 (12)0.0076 (10)0.0021 (9)0.0164 (10)
C50.0616 (14)0.0622 (13)0.0413 (11)0.0054 (11)0.0049 (10)0.0017 (10)
C60.0539 (12)0.0437 (11)0.0481 (12)0.0008 (9)0.0031 (9)0.0017 (9)
C70.0480 (11)0.0440 (11)0.0450 (11)0.0066 (9)0.0022 (9)0.0017 (8)
C80.0477 (12)0.0431 (10)0.0440 (11)0.0046 (9)0.0015 (8)0.0023 (8)
Cl10.0799 (5)0.0926 (5)0.0621 (4)0.0021 (4)0.0148 (3)0.0326 (3)
O10.1034 (14)0.0410 (8)0.0617 (10)0.0006 (8)0.0245 (9)0.0015 (7)
Geometric parameters (Å, º) top
C1—C21.392 (3)C4—Cl11.737 (2)
C1—C61.390 (3)C5—H50.9300
C1—C71.481 (3)C5—C61.372 (3)
C2—H20.9300C6—H60.9300
C2—C31.374 (3)C7—C81.488 (3)
C3—H30.9300C7—O11.218 (2)
C3—C41.369 (3)C8—C8i1.307 (4)
C4—C51.379 (3)C8—H80.9300
C2—C1—C7122.61 (18)C4—C5—H5120.6
C6—C1—C2118.30 (19)C6—C5—C4118.8 (2)
C6—C1—C7119.08 (18)C6—C5—H5120.6
C1—C2—H2119.6C1—C6—H6119.3
C3—C2—C1120.72 (19)C5—C6—C1121.3 (2)
C3—C2—H2119.6C5—C6—H6119.3
C2—C3—H3120.3C1—C7—C8119.63 (17)
C4—C3—C2119.4 (2)O1—C7—C1120.95 (18)
C4—C3—H3120.3O1—C7—C8119.41 (19)
C3—C4—C5121.4 (2)C7—C8—H8118.8
C3—C4—Cl1118.98 (17)C8i—C8—C7122.3 (2)
C5—C4—Cl1119.60 (17)C8i—C8—H8118.8
C1—C2—C3—C41.1 (3)C4—C5—C6—C10.4 (3)
C1—C7—C8—C8i178.2 (2)C6—C1—C2—C30.3 (3)
C2—C1—C6—C50.5 (3)C6—C1—C7—C8163.48 (18)
C2—C1—C7—C817.0 (3)C6—C1—C7—O115.6 (3)
C2—C1—C7—O1163.9 (2)C7—C1—C2—C3179.24 (19)
C2—C3—C4—C51.2 (3)C7—C1—C6—C5179.94 (19)
C2—C3—C4—Cl1178.37 (16)Cl1—C4—C5—C6179.15 (16)
C3—C4—C5—C60.4 (3)O1—C7—C8—C8i0.9 (4)
Symmetry code: (i) x, y+1, z+1.
(2E)-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione (2) top
Crystal data top
C16H10Br2O2F(000) = 384
Mr = 394.06Dx = 1.800 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.4391 (7) ÅCell parameters from 2527 reflections
b = 3.9937 (2) Åθ = 2.9–26.2°
c = 12.7244 (7) ŵ = 5.57 mm1
β = 97.827 (5)°T = 298 K
V = 726.92 (7) Å3Irregular, yellow
Z = 20.35 × 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-1Rint = 0.031
ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlisPro; Bourhis et al., 2015)
h = 1818
Tmin = 0.370, Tmax = 1.000k = 44
6231 measured reflectionsl = 1515
1470 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.08Δρmax = 0.36 e Å3
1470 reflectionsΔρmin = 0.43 e Å3
92 parametersExtinction correction: SHELXL-2016/4 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
Br10.06905 (2)0.86344 (8)0.66837 (3)0.05337 (16)
C10.31059 (19)0.3876 (7)0.5110 (2)0.0355 (6)
C20.3212 (2)0.4543 (8)0.6188 (2)0.0444 (7)
H20.3772300.4005350.6604700.053*
C30.2503 (2)0.5990 (8)0.6653 (2)0.0471 (8)
H30.2585170.6460560.7375430.057*
C40.1673 (2)0.6726 (6)0.6034 (2)0.0391 (7)
C50.1538 (2)0.6073 (7)0.4962 (2)0.0463 (7)
H50.0970520.6572530.4553120.056*
C60.2258 (2)0.4666 (8)0.4507 (2)0.0422 (7)
H60.2174970.4236320.3781540.051*
C70.3859 (2)0.2399 (8)0.4570 (2)0.0418 (7)
C80.4672 (2)0.0760 (7)0.5218 (2)0.0410 (7)
H80.4715610.0818560.5953990.049*
O10.38162 (17)0.2478 (7)0.36132 (17)0.0665 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0433 (2)0.0504 (2)0.0706 (3)0.00725 (15)0.02309 (16)0.00106 (17)
C10.0354 (15)0.0380 (14)0.0334 (15)0.0010 (12)0.0057 (12)0.0011 (12)
C20.0380 (17)0.0601 (19)0.0340 (16)0.0088 (14)0.0012 (13)0.0001 (14)
C30.0465 (18)0.0598 (19)0.0359 (16)0.0119 (15)0.0082 (13)0.0026 (15)
C40.0371 (16)0.0344 (15)0.0487 (18)0.0009 (12)0.0158 (13)0.0028 (13)
C50.0371 (16)0.0514 (18)0.0487 (18)0.0054 (14)0.0002 (13)0.0034 (15)
C60.0439 (17)0.0491 (17)0.0328 (15)0.0031 (14)0.0030 (13)0.0006 (13)
C70.0395 (16)0.0480 (16)0.0382 (17)0.0016 (13)0.0060 (13)0.0057 (13)
C80.0364 (16)0.0514 (18)0.0357 (15)0.0005 (13)0.0060 (12)0.0064 (14)
O10.0591 (15)0.109 (2)0.0322 (12)0.0232 (14)0.0078 (11)0.0071 (12)
Geometric parameters (Å, º) top
Br1—C41.896 (3)C4—C51.376 (4)
C1—C21.385 (4)C5—H50.9300
C1—C61.390 (4)C5—C61.377 (4)
C1—C71.485 (4)C6—H60.9300
C2—H20.9300C7—C81.492 (4)
C2—C31.378 (4)C7—O11.211 (3)
C3—H30.9300C8—C8i1.310 (5)
C3—C41.374 (4)C8—H80.9300
C2—C1—C6118.3 (3)C4—C5—H5120.6
C2—C1—C7123.1 (3)C4—C5—C6118.8 (3)
C6—C1—C7118.7 (3)C6—C5—H5120.6
C1—C2—H2119.4C1—C6—H6119.4
C3—C2—C1121.2 (3)C5—C6—C1121.3 (3)
C3—C2—H2119.4C5—C6—H6119.4
C2—C3—H3120.5C1—C7—C8119.3 (2)
C4—C3—C2119.0 (3)O1—C7—C1121.0 (3)
C4—C3—H3120.5O1—C7—C8119.7 (3)
C3—C4—Br1118.8 (2)C7—C8—H8119.0
C3—C4—C5121.5 (3)C8i—C8—C7121.9 (4)
C5—C4—Br1119.7 (2)C8i—C8—H8119.0
Br1—C4—C5—C6179.6 (2)C3—C4—C5—C60.4 (5)
C1—C2—C3—C41.0 (5)C4—C5—C6—C10.6 (5)
C1—C7—C8—C8i175.8 (3)C6—C1—C2—C30.8 (5)
C2—C1—C6—C50.1 (4)C6—C1—C7—C8164.8 (3)
C2—C1—C7—C816.0 (4)C6—C1—C7—O114.5 (4)
C2—C1—C7—O1164.7 (3)C7—C1—C2—C3178.4 (3)
C2—C3—C4—Br1178.8 (2)C7—C1—C6—C5179.3 (3)
C2—C3—C4—C50.5 (5)O1—C7—C8—C8i3.5 (6)
Symmetry code: (i) x+1, y, z+1.
 

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