Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chloro­phen­yl)-1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one

In the crystal, mol­ecules are linked by C—H...O hydrogen contacts, enclosing an (14) ring motif, and by a further C—H...O hydrogen contact, forming a two-dimensional supra­molecular structure extending along the direction parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.158
• Data-to-parameter ratio = 29.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.551 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 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
   2 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(2E)-3-(3-Chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H15ClO3	F(000) = 632
Mr = 302.74	Dx = 1.334 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8862 reflections
a = 9.0491 (4) Å	θ = 2.7–30.8°
b = 8.3257 (4) Å	µ = 0.26 mm^−1
c = 20.2857 (9) Å	T = 294 K
β = 99.484 (1)°	Block, yellow
V = 1507.44 (12) Å^3	0.40 × 0.24 × 0.19 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.036
φ and ω scans	θmax = 32.6°, θmin = 2.0°
39332 measured reflections	h = −13→13
5506 independent reflections	k = −12→12
3732 reflections with I > 2σ(I)	l = −30→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.3034P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
5506 reflections	Δρmax = 0.31 e Å^−3
190 parameters	Δρmin = −0.43 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.02901 (5)	1.02517 (6)	0.15452 (2)	0.0710 (2)
O1	1.07019 (12)	0.65283 (15)	0.35402 (5)	0.0576 (3)
O2	1.13649 (12)	0.52216 (16)	0.24887 (6)	0.0634 (4)
O3	0.67255 (12)	0.57110 (17)	0.07167 (5)	0.0632 (4)
C1	0.72153 (15)	0.73479 (17)	0.23869 (7)	0.0458 (4)
C2	0.82535 (15)	0.73642 (17)	0.29717 (7)	0.0463 (4)
C3	0.96267 (14)	0.66310 (15)	0.29901 (6)	0.0420 (3)
C4	0.99836 (14)	0.59071 (16)	0.24086 (6)	0.0415 (3)
C5	0.89499 (14)	0.59023 (15)	0.18335 (6)	0.0405 (3)
C6	0.75372 (13)	0.66142 (14)	0.18154 (6)	0.0394 (3)
C7	0.64331 (14)	0.64884 (17)	0.11929 (7)	0.0444 (4)
C8	0.49469 (15)	0.72588 (18)	0.11575 (7)	0.0495 (4)
C9	0.38379 (15)	0.69300 (18)	0.06640 (6)	0.0452 (4)
C10	0.22936 (14)	0.75164 (16)	0.05882 (6)	0.0424 (3)
C11	0.12555 (17)	0.69543 (19)	0.00574 (7)	0.0525 (4)
C12	−0.02283 (18)	0.7421 (2)	−0.00148 (8)	0.0610 (5)
C13	−0.07040 (16)	0.8446 (2)	0.04383 (8)	0.0564 (5)
C14	0.03261 (16)	0.90063 (17)	0.09633 (7)	0.0470 (4)
C15	0.18120 (15)	0.85720 (16)	0.10468 (7)	0.0447 (3)
C16	1.0326 (2)	0.7046 (3)	0.41599 (8)	0.0826 (7)
C17	1.1814 (2)	0.4431 (2)	0.19409 (9)	0.0669 (6)
H1A	0.62888	0.78375	0.23788	0.0550*
H2A	0.80242	0.78689	0.33512	0.0560*
H5A	0.91867	0.54216	0.14504	0.0490*
H8A	0.47900	0.79854	0.14872	0.0590*
H9A	0.40642	0.62539	0.03295	0.0540*
H11A	0.15612	0.62577	−0.02523	0.0630*
H12A	−0.09113	0.70376	−0.03734	0.0730*
H13A	−0.17036	0.87545	0.03911	0.0680*
H15A	0.24886	0.89746	0.14035	0.0540*
H16A	1.11764	0.69130	0.45069	0.1240*
H16B	1.00432	0.81587	0.41282	0.1240*
H16C	0.95044	0.64175	0.42628	0.1240*
H17A	1.28064	0.40096	0.20705	0.1000*
H17B	1.11330	0.35669	0.17988	0.1000*
H17C	1.18073	0.51778	0.15799	0.1000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0650 (3)	0.0704 (3)	0.0809 (3)	0.0083 (2)	0.0216 (2)	−0.0176 (2)
O1	0.0518 (6)	0.0735 (7)	0.0440 (5)	0.0124 (5)	−0.0028 (4)	−0.0031 (5)
O2	0.0487 (6)	0.0881 (8)	0.0518 (6)	0.0278 (5)	0.0039 (4)	−0.0044 (5)
O3	0.0479 (6)	0.0898 (8)	0.0505 (6)	0.0088 (5)	0.0038 (4)	−0.0226 (6)
C1	0.0400 (6)	0.0500 (7)	0.0472 (7)	0.0080 (5)	0.0064 (5)	−0.0052 (5)
C2	0.0462 (7)	0.0506 (7)	0.0420 (6)	0.0063 (5)	0.0074 (5)	−0.0069 (5)
C3	0.0425 (6)	0.0424 (6)	0.0398 (6)	0.0012 (5)	0.0028 (5)	0.0021 (5)
C4	0.0382 (6)	0.0423 (6)	0.0441 (6)	0.0057 (5)	0.0073 (5)	0.0033 (5)
C5	0.0404 (6)	0.0425 (6)	0.0396 (6)	0.0032 (5)	0.0093 (5)	−0.0010 (5)
C6	0.0382 (6)	0.0393 (5)	0.0403 (6)	0.0007 (4)	0.0057 (4)	−0.0005 (4)
C7	0.0384 (6)	0.0510 (7)	0.0434 (6)	0.0014 (5)	0.0055 (5)	−0.0046 (5)
C8	0.0426 (6)	0.0562 (8)	0.0476 (7)	0.0070 (6)	0.0014 (5)	−0.0090 (6)
C9	0.0424 (6)	0.0539 (7)	0.0388 (6)	0.0028 (5)	0.0050 (5)	−0.0017 (5)
C10	0.0401 (6)	0.0469 (6)	0.0384 (6)	−0.0001 (5)	0.0011 (5)	0.0006 (5)
C11	0.0493 (7)	0.0603 (8)	0.0449 (7)	0.0006 (6)	−0.0014 (6)	−0.0093 (6)
C12	0.0468 (8)	0.0733 (10)	0.0568 (8)	−0.0030 (7)	−0.0092 (6)	−0.0092 (7)
C13	0.0379 (6)	0.0642 (9)	0.0643 (9)	0.0002 (6)	−0.0002 (6)	0.0022 (7)
C14	0.0452 (7)	0.0445 (6)	0.0519 (7)	−0.0005 (5)	0.0094 (5)	0.0004 (5)
C15	0.0419 (6)	0.0476 (6)	0.0427 (6)	−0.0022 (5)	0.0016 (5)	−0.0030 (5)
C16	0.0814 (12)	0.1149 (17)	0.0452 (8)	0.0267 (12)	−0.0080 (8)	−0.0161 (10)
C17	0.0583 (9)	0.0781 (11)	0.0673 (10)	0.0238 (8)	0.0189 (8)	−0.0001 (8)

Geometric parameters (Å, º)

Cl1—C14	1.7310 (15)	C12—C13	1.374 (2)
O1—C3	1.3570 (16)	C13—C14	1.376 (2)
O1—C16	1.422 (2)	C14—C15	1.376 (2)
O2—C4	1.3593 (17)	C1—H1A	0.9300
O2—C17	1.408 (2)	C2—H2A	0.9300
O3—C7	1.2273 (18)	C5—H5A	0.9300
C1—C2	1.387 (2)	C8—H8A	0.9300
C1—C6	1.3832 (18)	C9—H9A	0.9300
C2—C3	1.3794 (19)	C11—H11A	0.9300
C3—C4	1.4088 (17)	C12—H12A	0.9300
C4—C5	1.3698 (17)	C13—H13A	0.9300
C5—C6	1.4041 (17)	C15—H15A	0.9300
C6—C7	1.4792 (18)	C16—H16A	0.9600
C7—C8	1.4810 (19)	C16—H16B	0.9600
C8—C9	1.3241 (19)	C16—H16C	0.9600
C9—C10	1.4643 (19)	C17—H17A	0.9600
C10—C11	1.3884 (19)	C17—H17B	0.9600
C10—C15	1.4005 (19)	C17—H17C	0.9600
C11—C12	1.382 (2)
C3—O1—C16	117.66 (12)	C6—C1—H1A	120.00
C4—O2—C17	118.77 (12)	C1—C2—H2A	120.00
C2—C1—C6	120.98 (13)	C3—C2—H2A	120.00
C1—C2—C3	119.94 (13)	C4—C5—H5A	120.00
O1—C3—C2	124.80 (12)	C6—C5—H5A	120.00
O1—C3—C4	115.43 (11)	C7—C8—H8A	119.00
C2—C3—C4	119.77 (12)	C9—C8—H8A	119.00
O2—C4—C3	114.38 (11)	C8—C9—H9A	116.00
O2—C4—C5	125.88 (12)	C10—C9—H9A	117.00
C3—C4—C5	119.72 (12)	C10—C11—H11A	120.00
C4—C5—C6	120.80 (11)	C12—C11—H11A	120.00
C1—C6—C5	118.76 (11)	C11—C12—H12A	120.00
C1—C6—C7	122.74 (11)	C13—C12—H12A	120.00
C5—C6—C7	118.45 (11)	C12—C13—H13A	121.00
O3—C7—C6	120.42 (12)	C14—C13—H13A	121.00
O3—C7—C8	120.14 (13)	C10—C15—H15A	120.00
C6—C7—C8	119.40 (12)	C14—C15—H15A	120.00
C7—C8—C9	121.08 (13)	O1—C16—H16A	109.00
C8—C9—C10	127.00 (13)	O1—C16—H16B	109.00
C9—C10—C11	118.76 (12)	O1—C16—H16C	109.00
C9—C10—C15	122.38 (12)	H16A—C16—H16B	109.00
C11—C10—C15	118.81 (12)	H16A—C16—H16C	109.00
C10—C11—C12	120.58 (14)	H16B—C16—H16C	109.00
C11—C12—C13	120.63 (15)	O2—C17—H17A	109.00
C12—C13—C14	118.77 (14)	O2—C17—H17B	109.00
Cl1—C14—C13	118.53 (11)	O2—C17—H17C	109.00
Cl1—C14—C15	119.45 (11)	H17A—C17—H17B	109.00
C13—C14—C15	122.00 (13)	H17A—C17—H17C	110.00
C10—C15—C14	119.21 (13)	H17B—C17—H17C	109.00
C2—C1—H1A	120.00
C16—O1—C3—C2	7.7 (2)	C1—C6—C7—C8	3.84 (19)
C16—O1—C3—C4	−171.77 (15)	C5—C6—C7—O3	3.5 (2)
C17—O2—C4—C3	178.44 (13)	C5—C6—C7—C8	−178.75 (12)
C17—O2—C4—C5	0.3 (2)	O3—C7—C8—C9	10.5 (2)
C6—C1—C2—C3	−0.5 (2)	C6—C7—C8—C9	−167.28 (13)
C2—C1—C6—C5	−1.0 (2)	C7—C8—C9—C10	175.76 (13)
C2—C1—C6—C7	176.44 (13)	C8—C9—C10—C11	−175.75 (15)
C1—C2—C3—O1	−177.65 (13)	C8—C9—C10—C15	1.6 (2)
C1—C2—C3—C4	1.8 (2)	C9—C10—C11—C12	177.04 (14)
O1—C3—C4—O2	−0.40 (17)	C15—C10—C11—C12	−0.4 (2)
O1—C3—C4—C5	177.86 (12)	C9—C10—C15—C14	−176.57 (13)
C2—C3—C4—O2	−179.87 (12)	C11—C10—C15—C14	0.8 (2)
C2—C3—C4—C5	−1.60 (19)	C10—C11—C12—C13	−0.2 (2)
O2—C4—C5—C6	178.20 (13)	C11—C12—C13—C14	0.4 (2)
C3—C4—C5—C6	0.2 (2)	C12—C13—C14—Cl1	−178.21 (12)
C4—C5—C6—C1	1.13 (19)	C12—C13—C14—C15	0.0 (2)
C4—C5—C6—C7	−176.39 (12)	Cl1—C14—C15—C10	177.64 (10)
C1—C6—C7—O3	−173.88 (14)	C13—C14—C15—C10	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3	0.93	2.45	2.7888 (18)	102
C11—H11A···O3^i	0.93	2.54	3.417 (2)	157
C15—H15A···O2^ii	0.93	2.54	3.4378 (18)	163

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2.