Crystal structure and Hirshfeld surface analysis of (E)-1-(3,5-di­chloro-2-hy­droxy­phen­yl)-3-(5-methyl­furan-2-yl)prop-2-en-1-one

The title chalcone derivative is almost planar, with a dihedral angle of 7.0 (2)° between the 3,5-di­chloro-2-hy­droxy­phenyl and 5-methyl­furan rings.

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT911_ALERT_3_B Missing FCF Refl Between Thmin & STh/L=    0.595        426 Report
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1 Check

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.006 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C14 H10 Cl2 O3
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.458 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.14 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             106.9 Degree
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        43% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          2 Units
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           2 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 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
   9 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

(E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-(5-methylfuran-\ 2-yl)prop-2-en-1-one

Crystal data

C14H10Cl2O3	F(000) = 608
Mr = 297.12	Dx = 1.508 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.831 (2) Å	Cell parameters from 3210 reflections
b = 4.4020 (5) Å	θ = 2.7–25.0°
c = 28.457 (5) Å	µ = 0.50 mm^−1
β = 105.254 (6)°	T = 290 K
V = 1309.0 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.28 × 0.25 mm

Data collection

Bruker APEXII diffractometer	2298 independent reflections
Radiation source: graphite	2232 reflections with I > 2σ(I)
Detector resolution: 0.820 pixels mm^-1	Rint = 0.032
SAINT (Bruker, 2006) scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −12→12
Tmin = 0.862, Tmax = 0.906	k = −5→4
2940 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.215	w = 1/[σ^2(Fo^2) + (0.1367P)^2 + 0.3086P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2298 reflections	Δρmax = 0.30 e Å^−3
174 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2523 (3)	−0.4421 (6)	−0.16266 (9)	0.0723 (9)
C2	0.1549 (5)	−0.6402 (10)	−0.18009 (16)	0.0753 (13)
C3	0.1426 (5)	−0.6924 (10)	−0.22703 (16)	0.0762 (13)
H3	0.082501	−0.819559	−0.246999	0.091*
C4	0.2352 (5)	−0.5237 (9)	−0.24105 (13)	0.0707 (12)
H4	0.248630	−0.517334	−0.272006	0.085*
C5	0.3028 (5)	−0.3696 (9)	−0.20109 (13)	0.0657 (12)
C6	0.0879 (6)	−0.7575 (13)	−0.1441 (2)	0.1026 (19)
H6A	0.020336	−0.892412	−0.160150	0.154*
H6B	0.052540	−0.590266	−0.130271	0.154*
H6C	0.147806	−0.865048	−0.118645	0.154*
C7	0.4044 (4)	−0.1635 (8)	−0.19346 (13)	0.0640 (11)
H7	0.433954	−0.117117	−0.220490	0.077*
C8	0.4640 (4)	−0.0255 (8)	−0.15184 (12)	0.0650 (11)
H8	0.438851	−0.064204	−0.123590	0.078*
C9	0.5671 (4)	0.1829 (8)	−0.15071 (12)	0.0614 (11)
O10	0.5944 (3)	0.2504 (7)	−0.18937 (9)	0.0766 (10)
C11	0.6450 (4)	0.3207 (8)	−0.10472 (12)	0.0612 (11)
C12	0.6189 (5)	0.2587 (9)	−0.05990 (13)	0.0688 (12)
H12	0.550905	0.132823	−0.058535	0.083*
C13	0.6944 (5)	0.3854 (11)	−0.01815 (13)	0.0777 (14)
C14	0.7946 (5)	0.5709 (10)	−0.01895 (13)	0.0773 (14)
H14	0.845172	0.653156	0.009816	0.093*
C15	0.8201 (5)	0.6350 (9)	−0.06256 (14)	0.0683 (12)
C16	0.7460 (4)	0.5130 (9)	−0.10592 (12)	0.0628 (11)
O17	0.7747 (3)	0.5862 (7)	−0.14744 (9)	0.0786 (9)
H17	0.724256	0.502456	−0.170370	0.118*
Cl18	0.94733 (14)	0.8606 (3)	−0.06462 (4)	0.0898 (6)
Cl19	0.66403 (17)	0.3052 (4)	0.03742 (4)	0.1139 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.081 (3)	0.0853 (18)	0.0574 (15)	−0.0008 (16)	0.0296 (13)	−0.0014 (12)
C2	0.073 (4)	0.080 (3)	0.076 (3)	−0.001 (2)	0.025 (2)	0.000 (2)
C3	0.072 (4)	0.080 (3)	0.073 (3)	−0.002 (2)	0.012 (2)	−0.0048 (19)
C4	0.075 (4)	0.079 (2)	0.057 (2)	0.000 (2)	0.0147 (18)	−0.0015 (17)
C5	0.072 (4)	0.074 (2)	0.053 (2)	0.012 (2)	0.0199 (17)	0.0040 (15)
C6	0.101 (6)	0.114 (4)	0.108 (4)	−0.012 (3)	0.055 (3)	0.003 (3)
C7	0.066 (4)	0.073 (2)	0.054 (2)	0.005 (2)	0.0184 (17)	0.0058 (15)
C8	0.077 (4)	0.071 (2)	0.0495 (19)	0.002 (2)	0.0218 (17)	0.0082 (15)
C9	0.070 (4)	0.069 (2)	0.0466 (19)	0.0047 (19)	0.0188 (17)	0.0031 (14)
O10	0.090 (3)	0.0963 (19)	0.0489 (15)	−0.0065 (16)	0.0272 (13)	0.0015 (12)
C11	0.062 (3)	0.076 (2)	0.0471 (19)	0.0067 (19)	0.0168 (16)	0.0021 (15)
C12	0.074 (4)	0.085 (2)	0.049 (2)	−0.005 (2)	0.0183 (17)	0.0051 (17)
C13	0.092 (4)	0.095 (3)	0.050 (2)	−0.001 (3)	0.025 (2)	0.0022 (19)
C14	0.088 (4)	0.089 (3)	0.052 (2)	−0.001 (3)	0.0136 (19)	−0.0048 (18)
C15	0.071 (4)	0.073 (2)	0.062 (2)	−0.002 (2)	0.0202 (19)	−0.0013 (17)
C16	0.061 (3)	0.076 (2)	0.0537 (19)	0.004 (2)	0.0202 (16)	0.0046 (16)
O17	0.086 (3)	0.0982 (19)	0.0562 (15)	−0.0112 (17)	0.0270 (13)	0.0045 (13)
Cl18	0.0900 (14)	0.0995 (9)	0.0818 (8)	−0.0179 (7)	0.0260 (6)	−0.0063 (5)
Cl19	0.1348 (17)	0.1627 (14)	0.0488 (7)	−0.0341 (10)	0.0326 (7)	−0.0011 (6)

Geometric parameters (Å, º)

O1—C2	1.358 (6)	C8—H8	0.9300
O1—C5	1.382 (5)	C9—O10	1.248 (4)
C2—C3	1.327 (6)	C9—C11	1.487 (5)
C2—C6	1.495 (6)	C11—C16	1.390 (6)
C3—C4	1.389 (7)	C11—C12	1.404 (5)
C3—H3	0.9300	C12—C13	1.372 (6)
C4—C5	1.361 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.363 (6)
C5—C7	1.399 (6)	C13—Cl19	1.734 (4)
C6—H6A	0.9600	C14—C15	1.370 (5)
C6—H6B	0.9600	C14—H14	0.9300
C6—H6C	0.9600	C15—C16	1.391 (5)
C7—C8	1.337 (5)	C15—Cl18	1.712 (5)
C7—H7	0.9300	C16—O17	1.338 (4)
C8—C9	1.439 (6)	O17—H17	0.8200
C2—O1—C5	106.9 (3)	C9—C8—H8	120.0
C3—C2—O1	110.0 (4)	O10—C9—C8	119.6 (3)
C3—C2—C6	133.8 (5)	O10—C9—C11	117.9 (4)
O1—C2—C6	116.2 (4)	C8—C9—C11	122.5 (3)
C2—C3—C4	107.9 (4)	C16—C11—C12	119.3 (3)
C2—C3—H3	126.0	C16—C11—C9	119.7 (3)
C4—C3—H3	126.0	C12—C11—C9	121.1 (4)
C5—C4—C3	107.3 (4)	C13—C12—C11	119.4 (4)
C5—C4—H4	126.4	C13—C12—H12	120.3
C3—C4—H4	126.4	C11—C12—H12	120.3
C4—C5—O1	108.0 (4)	C14—C13—C12	121.7 (4)
C4—C5—C7	133.0 (4)	C14—C13—Cl19	118.7 (3)
O1—C5—C7	119.1 (3)	C12—C13—Cl19	119.6 (4)
C2—C6—H6A	109.5	C13—C14—C15	119.3 (4)
C2—C6—H6B	109.5	C13—C14—H14	120.3
H6A—C6—H6B	109.5	C15—C14—H14	120.3
C2—C6—H6C	109.5	C14—C15—C16	121.1 (4)
H6A—C6—H6C	109.5	C14—C15—Cl18	120.4 (3)
H6B—C6—H6C	109.5	C16—C15—Cl18	118.4 (3)
C8—C7—C5	127.5 (4)	O17—C16—C11	122.4 (3)
C8—C7—H7	116.2	O17—C16—C15	118.4 (4)
C5—C7—H7	116.2	C11—C16—C15	119.2 (3)
C7—C8—C9	120.0 (3)	C16—O17—H17	109.5
C7—C8—H8	120.0
C5—O1—C2—C3	−0.2 (5)	C8—C9—C11—C12	−1.7 (6)
C5—O1—C2—C6	178.3 (4)	C16—C11—C12—C13	−0.9 (6)
O1—C2—C3—C4	0.1 (6)	C9—C11—C12—C13	178.7 (4)
C6—C2—C3—C4	−178.0 (6)	C11—C12—C13—C14	0.1 (7)
C2—C3—C4—C5	−0.1 (5)	C11—C12—C13—Cl19	−179.1 (3)
C3—C4—C5—O1	0.0 (5)	C12—C13—C14—C15	0.6 (7)
C3—C4—C5—C7	−178.7 (5)	Cl19—C13—C14—C15	179.7 (3)
C2—O1—C5—C4	0.1 (5)	C13—C14—C15—C16	−0.3 (7)
C2—O1—C5—C7	179.0 (4)	C13—C14—C15—Cl18	−178.6 (4)
C4—C5—C7—C8	−179.8 (4)	C12—C11—C16—O17	−178.7 (4)
O1—C5—C7—C8	1.6 (7)	C9—C11—C16—O17	1.6 (6)
C5—C7—C8—C9	−179.6 (4)	C12—C11—C16—C15	1.2 (6)
C7—C8—C9—O10	5.1 (6)	C9—C11—C16—C15	−178.5 (4)
C7—C8—C9—C11	−174.1 (4)	C14—C15—C16—O17	179.4 (4)
O10—C9—C11—C16	−1.2 (6)	Cl18—C15—C16—O17	−2.3 (6)
C8—C9—C11—C16	178.0 (4)	C14—C15—C16—C11	−0.6 (7)
O10—C9—C11—C12	179.1 (4)	Cl18—C15—C16—C11	177.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17···O10	0.82	1.76	2.489 (4)	147
C4—H4···O10^i	0.93	2.54	3.272 (6)	135
C7—H7···O10^i	0.93	2.57	3.359 (4)	143

Symmetry code: (i) −x+1, y−1/2, −z−1/2.