1-Phenyl-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one

In the title compound, C₁₈H₁₈O₄, the dihedral angle between the benzene rings is 9.07 (7)°. Inter­molecular C—H...O inter­actions form chains along the c axis. The crystal structure is further stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O4     -   C14     ..       7.27 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.645
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.58
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.64 e/A   3

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C18H18O4	F(000) = 632
Mr = 298.32	Dx = 1.326 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5611 reflections
a = 13.5136 (4) Å	θ = 2.8–25.0°
b = 7.8414 (3) Å	µ = 0.09 mm^−1
c = 14.9854 (5) Å	T = 120 K
β = 109.823 (2)°	Rhombohedral, yellow
V = 1493.84 (9) Å^3	0.68 × 0.66 × 0.48 mm
Z = 4

Data collection

Brucker SMART APEX2 CCD area-detector diffractometer	2632 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.8°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.862, Tmax = 0.957	l = −17→17
13327 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 1.0117P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2632 reflections	Δρmax = 0.65 e Å^−3
203 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.04274 (8)	0.30260 (13)	0.49490 (7)	0.0269 (3)
O2	0.30832 (8)	0.64014 (14)	0.17284 (7)	0.0254 (3)
O3	0.47653 (8)	0.79725 (13)	0.29036 (7)	0.0243 (3)
O4	0.51875 (8)	0.80019 (13)	0.47994 (7)	0.0262 (3)
C1	0.18572 (11)	0.49287 (18)	0.72405 (10)	0.0224 (3)
H1	0.2409	0.5494	0.7100	0.027*
C2	0.18054 (11)	0.50241 (19)	0.81491 (10)	0.0244 (3)
H2	0.2316	0.5665	0.8624	0.029*
C3	0.10126 (11)	0.41885 (19)	0.83652 (10)	0.0241 (3)
H3	0.0978	0.4255	0.8987	0.029*
C4	0.02679 (11)	0.32519 (19)	0.76682 (10)	0.0251 (3)
H4	−0.0273	0.2669	0.7816	0.030*
C5	0.03117 (11)	0.31655 (18)	0.67607 (10)	0.0229 (3)
H5	−0.0203	0.2527	0.6288	0.027*
C6	0.11053 (11)	0.40087 (17)	0.65322 (10)	0.0199 (3)
C7	0.11017 (11)	0.38856 (18)	0.55327 (10)	0.0206 (3)
C8	0.19210 (11)	0.47937 (18)	0.52712 (10)	0.0219 (3)
H8	0.2445	0.5423	0.5741	0.026*
C9	0.19381 (11)	0.47465 (18)	0.43858 (10)	0.0215 (3)
H9	0.1393	0.4115	0.3938	0.026*
C10	0.27044 (11)	0.55594 (18)	0.40290 (10)	0.0203 (3)
C11	0.25183 (11)	0.55209 (18)	0.30529 (10)	0.0210 (3)
H11	0.1916	0.4949	0.2642	0.025*
C12	0.32140 (11)	0.63196 (18)	0.26823 (9)	0.0202 (3)
C13	0.41110 (11)	0.71328 (18)	0.32859 (10)	0.0201 (3)
C14	0.42983 (11)	0.71604 (18)	0.42681 (10)	0.0203 (3)
C15	0.35989 (11)	0.63815 (18)	0.46358 (10)	0.0207 (3)
H15	0.3727	0.6406	0.5299	0.025*
C16	0.21490 (13)	0.5707 (2)	0.10838 (10)	0.0329 (4)
H16A	0.2149	0.5851	0.0434	0.049*
H16B	0.1540	0.6299	0.1153	0.049*
H16C	0.2110	0.4490	0.1217	0.049*
C17	0.57785 (12)	0.7181 (2)	0.31140 (11)	0.0286 (4)
H17A	0.6197	0.7824	0.2809	0.043*
H17B	0.5688	0.6007	0.2875	0.043*
H17C	0.6141	0.7171	0.3802	0.043*
C18	0.54150 (12)	0.8014 (2)	0.58011 (10)	0.0288 (4)
H18A	0.6072	0.8636	0.6107	0.043*
H18B	0.5490	0.6838	0.6037	0.043*
H18C	0.4840	0.8574	0.5947	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0271 (6)	0.0286 (6)	0.0257 (5)	−0.0064 (5)	0.0096 (4)	−0.0061 (4)
O2	0.0264 (5)	0.0313 (6)	0.0195 (5)	0.0008 (4)	0.0090 (4)	0.0041 (4)
O3	0.0244 (5)	0.0257 (6)	0.0239 (5)	−0.0005 (4)	0.0097 (4)	0.0055 (4)
O4	0.0291 (6)	0.0281 (6)	0.0229 (5)	−0.0058 (5)	0.0107 (4)	−0.0003 (4)
C1	0.0223 (7)	0.0206 (7)	0.0254 (7)	−0.0013 (6)	0.0093 (6)	0.0006 (6)
C2	0.0260 (7)	0.0227 (7)	0.0228 (7)	−0.0005 (6)	0.0058 (6)	−0.0010 (6)
C3	0.0285 (8)	0.0238 (7)	0.0212 (7)	0.0041 (6)	0.0099 (6)	0.0041 (6)
C4	0.0220 (7)	0.0267 (8)	0.0279 (8)	0.0005 (6)	0.0101 (6)	0.0062 (6)
C5	0.0200 (7)	0.0228 (7)	0.0238 (7)	−0.0002 (6)	0.0048 (6)	0.0027 (6)
C6	0.0194 (7)	0.0171 (7)	0.0229 (7)	0.0034 (6)	0.0067 (6)	0.0022 (6)
C7	0.0196 (7)	0.0175 (7)	0.0237 (7)	0.0030 (6)	0.0060 (6)	0.0006 (6)
C8	0.0205 (7)	0.0215 (7)	0.0228 (7)	−0.0006 (6)	0.0063 (6)	−0.0004 (6)
C9	0.0207 (7)	0.0187 (7)	0.0238 (7)	0.0010 (6)	0.0057 (6)	0.0000 (6)
C10	0.0215 (7)	0.0178 (7)	0.0216 (7)	0.0032 (6)	0.0073 (6)	0.0012 (6)
C11	0.0202 (7)	0.0197 (7)	0.0212 (7)	0.0012 (6)	0.0046 (6)	−0.0015 (6)
C12	0.0246 (7)	0.0192 (7)	0.0164 (7)	0.0051 (6)	0.0064 (6)	0.0008 (5)
C13	0.0217 (7)	0.0179 (7)	0.0214 (7)	0.0029 (6)	0.0083 (6)	0.0033 (6)
C14	0.0191 (7)	0.0178 (7)	0.0216 (7)	0.0005 (6)	0.0036 (5)	−0.0005 (6)
C15	0.0237 (7)	0.0209 (7)	0.0174 (7)	0.0021 (6)	0.0066 (6)	0.0011 (6)
C16	0.0408 (9)	0.0370 (9)	0.0190 (7)	−0.0053 (8)	0.0076 (7)	−0.0022 (7)
C17	0.0245 (8)	0.0358 (9)	0.0276 (8)	−0.0001 (7)	0.0114 (6)	0.0014 (7)
C18	0.0285 (8)	0.0322 (9)	0.0214 (8)	−0.0059 (7)	0.0028 (6)	−0.0030 (6)

Geometric parameters (Å, º)

O1—C7	1.2285 (17)	C8—H8	0.95
O2—C12	1.3810 (16)	C9—C10	1.463 (2)
O2—C16	1.4129 (19)	C9—H9	0.95
O3—C13	1.3737 (17)	C10—C11	1.3980 (19)
O3—C17	1.4376 (18)	C10—C15	1.399 (2)
O4—C14	1.3654 (17)	C11—C12	1.392 (2)
O4—C18	1.4265 (17)	C11—H11	0.95
C1—C2	1.389 (2)	C12—C13	1.397 (2)
C1—C6	1.396 (2)	C13—C14	1.4065 (19)
C1—H1	0.95	C14—C15	1.387 (2)
C2—C3	1.385 (2)	C15—H15	0.95
C2—H2	0.95	C16—H16A	0.98
C3—C4	1.389 (2)	C16—H16B	0.98
C3—H3	0.95	C16—H16C	0.98
C4—C5	1.383 (2)	C17—H17A	0.98
C4—H4	0.95	C17—H17B	0.98
C5—C6	1.398 (2)	C17—H17C	0.98
C5—H5	0.95	C18—H18A	0.98
C6—C7	1.4992 (19)	C18—H18B	0.98
C7—C8	1.477 (2)	C18—H18C	0.98
C8—C9	1.335 (2)
C12—O2—C16	117.44 (11)	C12—C11—C10	120.10 (13)
C13—O3—C17	113.67 (11)	C12—C11—H11	120.0
C14—O4—C18	116.73 (11)	C10—C11—H11	120.0
C2—C1—C6	120.52 (13)	O2—C12—C11	124.54 (12)
C2—C1—H1	119.7	O2—C12—C13	115.31 (12)
C6—C1—H1	119.7	C11—C12—C13	120.14 (12)
C3—C2—C1	120.26 (14)	O3—C13—C12	119.26 (12)
C3—C2—H2	119.9	O3—C13—C14	121.07 (12)
C1—C2—H2	119.9	C12—C13—C14	119.57 (13)
C2—C3—C4	119.66 (13)	O4—C14—C15	124.38 (12)
C2—C3—H3	120.2	O4—C14—C13	115.35 (12)
C4—C3—H3	120.2	C15—C14—C13	120.26 (13)
C5—C4—C3	120.24 (13)	C14—C15—C10	119.98 (13)
C5—C4—H4	119.9	C14—C15—H15	120.0
C3—C4—H4	119.9	C10—C15—H15	120.0
C4—C5—C6	120.67 (13)	O2—C16—H16A	109.5
C4—C5—H5	119.7	O2—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C1—C6—C5	118.64 (13)	O2—C16—H16C	109.5
C1—C6—C7	123.23 (12)	H16A—C16—H16C	109.5
C5—C6—C7	118.13 (12)	H16B—C16—H16C	109.5
O1—C7—C8	121.16 (13)	O3—C17—H17A	109.5
O1—C7—C6	119.80 (12)	O3—C17—H17B	109.5
C8—C7—C6	119.03 (12)	H17A—C17—H17B	109.5
C9—C8—C7	121.16 (13)	O3—C17—H17C	109.5
C9—C8—H8	119.4	H17A—C17—H17C	109.5
C7—C8—H8	119.4	H17B—C17—H17C	109.5
C8—C9—C10	127.16 (13)	O4—C18—H18A	109.5
C8—C9—H9	116.4	O4—C18—H18B	109.5
C10—C9—H9	116.4	H18A—C18—H18B	109.5
C11—C10—C15	119.94 (13)	O4—C18—H18C	109.5
C11—C10—C9	118.34 (12)	H18A—C18—H18C	109.5
C15—C10—C9	121.72 (12)	H18B—C18—H18C	109.5
C6—C1—C2—C3	0.8 (2)	C16—O2—C12—C13	−175.46 (13)
C1—C2—C3—C4	0.0 (2)	C10—C11—C12—O2	−177.82 (12)
C2—C3—C4—C5	−0.6 (2)	C10—C11—C12—C13	1.3 (2)
C3—C4—C5—C6	0.3 (2)	C17—O3—C13—C12	−112.18 (14)
C2—C1—C6—C5	−1.0 (2)	C17—O3—C13—C14	71.41 (16)
C2—C1—C6—C7	178.63 (13)	O2—C12—C13—O3	1.79 (18)
C4—C5—C6—C1	0.5 (2)	C11—C12—C13—O3	−177.39 (12)
C4—C5—C6—C7	−179.18 (13)	O2—C12—C13—C14	178.25 (12)
C1—C6—C7—O1	178.60 (13)	C11—C12—C13—C14	−0.9 (2)
C5—C6—C7—O1	−1.75 (19)	C18—O4—C14—C15	2.2 (2)
C1—C6—C7—C8	−0.8 (2)	C18—O4—C14—C13	−178.36 (12)
C5—C6—C7—C8	178.85 (12)	O3—C13—C14—O4	−2.85 (19)
O1—C7—C8—C9	1.8 (2)	C12—C13—C14—O4	−179.25 (12)
C6—C7—C8—C9	−178.78 (13)	O3—C13—C14—C15	176.58 (12)
C7—C8—C9—C10	−179.13 (13)	C12—C13—C14—C15	0.2 (2)
C8—C9—C10—C11	−172.83 (14)	O4—C14—C15—C10	179.57 (13)
C8—C9—C10—C15	6.3 (2)	C13—C14—C15—C10	0.2 (2)
C15—C10—C11—C12	−0.9 (2)	C11—C10—C15—C14	0.2 (2)
C9—C10—C11—C12	178.28 (12)	C9—C10—C15—C14	−178.98 (13)
C16—O2—C12—C11	3.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	0.95	2.56	3.248 (2)	129
C9—H9···O1	0.95	2.46	2.805 (2)	101
C17—H17C···O4	0.98	2.37	2.966 (2)	118
C2—H2···Cg^ii	0.95	2.76	3.500 (2)	135

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