3,4-Dimethoxy­chalcone

In the title mol­ecule, C₁₇H₁₆O₃, the dihedral angle between the benzene rings is 25.75 (3)°. The crystal packing is stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.27

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           39.10
           From the CIF: _reflns_number_total               4202
           Count of symmetry unique reflns         4207
           Completeness (_total/calc)             99.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   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
   0 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.

Author Response: H.K. Fun and I.A. Razak are supervisors of Jeannie B.-J. Teh whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and V. Shettigar in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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).

3,4-Dimethoxychalcone

Crystal data

C17H16O3	F(000) = 2272
Mr = 268.30	Dx = 1.330 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 6250 reflections
a = 27.7541 (4) Å	θ = 1.9–39.1°
b = 34.1948 (4) Å	µ = 0.09 mm^−1
c = 5.6487 (1) Å	T = 100 K
V = 5360.88 (14) Å^3	Block, yellow
Z = 16	0.51 × 0.37 × 0.33 mm

Data collection

Brucker SMART APEX2 CCD area-detector diffractometer	4202 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm^-1	θmax = 39.1°, θmin = 1.9°
ω scans	h = −48→49
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −60→55
Tmin = 0.882, Tmax = 0.971	l = −9→9
41010 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 1.2638P] where P = (Fo^2 + 2Fc^2)/3
4202 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.43 e Å^−3
1 restraint	Δρmin = −0.19 e Å^−3

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	0.53281 (3)	0.07319 (3)	−0.34973 (16)	0.02852 (19)
O2	0.29358 (3)	0.06721 (2)	0.19859 (16)	0.01987 (15)
O3	0.30342 (3)	0.02278 (2)	0.56221 (15)	0.01910 (14)
C1	0.62031 (4)	0.06420 (3)	0.11941 (19)	0.01817 (16)
H1A	0.6035	0.0481	0.2231	0.022*
C2	0.66863 (4)	0.07310 (3)	0.1631 (2)	0.02060 (18)
H2A	0.6842	0.0621	0.2927	0.025*
C3	0.69353 (4)	0.09837 (3)	0.0135 (2)	0.01991 (17)
H3A	0.7256	0.1044	0.0436	0.024*
C4	0.67020 (4)	0.11471 (3)	−0.1819 (2)	0.01903 (17)
H4A	0.6864	0.1322	−0.2792	0.023*
C5	0.62266 (4)	0.10473 (3)	−0.23081 (19)	0.01755 (16)
H5A	0.6076	0.1149	−0.3644	0.021*
C6	0.59729 (3)	0.07951 (3)	−0.08025 (18)	0.01489 (14)
C7	0.54613 (3)	0.06996 (3)	−0.14283 (18)	0.01724 (16)
C8	0.51258 (3)	0.05862 (3)	0.04833 (18)	0.01668 (15)
H8A	0.5241	0.0517	0.1972	0.020*
C9	0.46485 (3)	0.05849 (3)	0.00222 (19)	0.01581 (15)
H9A	0.4560	0.0648	−0.1519	0.019*
C10	0.42538 (3)	0.04967 (3)	0.16424 (17)	0.01460 (14)
C11	0.37894 (3)	0.06310 (3)	0.10095 (18)	0.01509 (14)
H11A	0.3749	0.0776	−0.0370	0.018*
C12	0.33943 (3)	0.05493 (3)	0.24211 (18)	0.01480 (14)
C13	0.34501 (3)	0.03140 (3)	0.44605 (18)	0.01447 (14)
C14	0.39091 (3)	0.01889 (3)	0.51160 (18)	0.01596 (15)
H14A	0.3949	0.0041	0.6484	0.019*
C15	0.43090 (3)	0.02839 (3)	0.37332 (18)	0.01565 (15)
H15A	0.4615	0.0205	0.4209	0.019*
C16	0.28695 (4)	0.09353 (3)	0.0052 (2)	0.02065 (17)
H16A	0.2538	0.1014	−0.0020	0.031*
H16B	0.2956	0.0807	−0.1399	0.031*
H16C	0.3070	0.1161	0.0274	0.031*
C17	0.30589 (4)	−0.00594 (3)	0.7473 (2)	0.01967 (17)
H17A	0.2740	−0.0113	0.8050	0.030*
H17B	0.3254	0.0038	0.8744	0.030*
H17C	0.3199	−0.0296	0.6864	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0187 (3)	0.0528 (6)	0.0141 (3)	−0.0041 (3)	−0.0013 (3)	0.0020 (3)
O2	0.0121 (3)	0.0247 (3)	0.0228 (4)	0.0015 (2)	0.0002 (2)	0.0056 (3)
O3	0.0149 (3)	0.0226 (3)	0.0198 (3)	−0.0009 (2)	0.0029 (2)	0.0041 (3)
C1	0.0164 (4)	0.0230 (4)	0.0151 (4)	−0.0022 (3)	−0.0008 (3)	0.0043 (3)
C2	0.0170 (4)	0.0280 (5)	0.0168 (4)	−0.0022 (3)	−0.0023 (3)	0.0033 (4)
C3	0.0158 (4)	0.0236 (4)	0.0203 (4)	−0.0042 (3)	−0.0002 (3)	−0.0007 (3)
C4	0.0187 (4)	0.0185 (4)	0.0199 (4)	−0.0026 (3)	0.0035 (3)	0.0022 (3)
C5	0.0173 (3)	0.0188 (4)	0.0166 (4)	0.0007 (3)	0.0015 (3)	0.0043 (3)
C6	0.0137 (3)	0.0174 (4)	0.0135 (3)	−0.0001 (3)	0.0009 (3)	0.0007 (3)
C7	0.0143 (3)	0.0228 (4)	0.0146 (4)	−0.0003 (3)	0.0002 (3)	0.0002 (3)
C8	0.0142 (3)	0.0207 (4)	0.0151 (4)	−0.0005 (3)	0.0008 (3)	0.0003 (3)
C9	0.0135 (3)	0.0185 (3)	0.0154 (4)	−0.0010 (3)	0.0005 (3)	−0.0012 (3)
C10	0.0124 (3)	0.0164 (3)	0.0150 (4)	−0.0008 (3)	0.0002 (3)	−0.0019 (3)
C11	0.0132 (3)	0.0172 (3)	0.0149 (3)	−0.0007 (3)	0.0000 (3)	0.0006 (3)
C12	0.0125 (3)	0.0162 (3)	0.0157 (4)	0.0001 (3)	0.0001 (3)	−0.0001 (3)
C13	0.0140 (3)	0.0152 (3)	0.0143 (3)	−0.0013 (3)	0.0009 (3)	−0.0008 (3)
C14	0.0154 (3)	0.0167 (3)	0.0158 (4)	0.0000 (3)	−0.0006 (3)	0.0005 (3)
C15	0.0134 (3)	0.0172 (4)	0.0164 (4)	0.0008 (3)	−0.0004 (3)	−0.0003 (3)
C16	0.0176 (4)	0.0244 (4)	0.0199 (4)	0.0030 (3)	−0.0027 (3)	0.0028 (4)
C17	0.0210 (4)	0.0203 (4)	0.0177 (4)	−0.0039 (3)	0.0025 (3)	0.0017 (3)

Geometric parameters (Å, º)

O1—C7	1.2307 (13)	C8—H8A	0.9300
O2—C12	1.3624 (11)	C9—C10	1.4592 (13)
O2—C16	1.4271 (13)	C9—H9A	0.9300
O3—C13	1.3599 (12)	C10—C15	1.3956 (14)
O3—C17	1.4362 (13)	C10—C11	1.4141 (13)
C1—C2	1.3972 (14)	C11—C12	1.3843 (13)
C1—C6	1.3979 (14)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.4138 (14)
C2—C3	1.3922 (15)	C13—C14	1.3939 (13)
C2—H2A	0.9300	C14—C15	1.3956 (14)
C3—C4	1.3962 (16)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.3907 (14)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.4009 (13)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.4995 (13)	C17—H17B	0.9600
C7—C8	1.4776 (14)	C17—H17C	0.9600
C8—C9	1.3498 (13)
C12—O2—C16	116.93 (8)	C15—C10—C9	123.78 (8)
C13—O3—C17	117.32 (8)	C11—C10—C9	117.30 (9)
C2—C1—C6	119.96 (9)	C12—C11—C10	120.71 (9)
C2—C1—H1A	120.0	C12—C11—H11A	119.6
C6—C1—H1A	120.0	C10—C11—H11A	119.6
C3—C2—C1	120.30 (10)	O2—C12—C11	125.01 (9)
C3—C2—H2A	119.8	O2—C12—C13	115.13 (8)
C1—C2—H2A	119.8	C11—C12—C13	119.84 (8)
C2—C3—C4	119.87 (9)	O3—C13—C14	125.52 (9)
C2—C3—H3A	120.1	O3—C13—C12	115.06 (8)
C4—C3—H3A	120.1	C14—C13—C12	119.41 (8)
C5—C4—C3	119.92 (9)	C13—C14—C15	120.45 (9)
C5—C4—H4A	120.0	C13—C14—H14A	119.8
C3—C4—H4A	120.0	C15—C14—H14A	119.8
C4—C5—C6	120.48 (9)	C14—C15—C10	120.51 (9)
C4—C5—H5A	119.8	C14—C15—H15A	119.7
C6—C5—H5A	119.8	C10—C15—H15A	119.7
C1—C6—C5	119.39 (9)	O2—C16—H16A	109.5
C1—C6—C7	122.77 (9)	O2—C16—H16B	109.5
C5—C6—C7	117.84 (9)	H16A—C16—H16B	109.5
O1—C7—C8	121.89 (9)	O2—C16—H16C	109.5
O1—C7—C6	119.25 (9)	H16A—C16—H16C	109.5
C8—C7—C6	118.80 (9)	H16B—C16—H16C	109.5
C9—C8—C7	118.57 (9)	O3—C17—H17A	109.5
C9—C8—H8A	120.7	O3—C17—H17B	109.5
C7—C8—H8A	120.7	H17A—C17—H17B	109.5
C8—C9—C10	128.06 (10)	O3—C17—H17C	109.5
C8—C9—H9A	116.0	H17A—C17—H17C	109.5
C10—C9—H9A	116.0	H17B—C17—H17C	109.5
C15—C10—C11	118.91 (8)
C6—C1—C2—C3	2.44 (17)	C15—C10—C11—C12	−0.78 (14)
C1—C2—C3—C4	−0.39 (17)	C9—C10—C11—C12	178.15 (9)
C2—C3—C4—C5	−2.05 (16)	C16—O2—C12—C11	−6.29 (15)
C3—C4—C5—C6	2.45 (16)	C16—O2—C12—C13	175.24 (9)
C2—C1—C6—C5	−2.04 (16)	C10—C11—C12—O2	178.64 (9)
C2—C1—C6—C7	177.61 (10)	C10—C11—C12—C13	−2.96 (14)
C4—C5—C6—C1	−0.40 (15)	C17—O3—C13—C14	−9.36 (14)
C4—C5—C6—C7	179.93 (9)	C17—O3—C13—C12	170.33 (9)
C1—C6—C7—O1	−156.45 (11)	O2—C12—C13—O3	3.23 (13)
C5—C6—C7—O1	23.20 (15)	C11—C12—C13—O3	−175.33 (9)
C1—C6—C7—C8	26.29 (14)	O2—C12—C13—C14	−177.06 (9)
C5—C6—C7—C8	−154.06 (9)	C11—C12—C13—C14	4.38 (14)
O1—C7—C8—C9	−11.70 (16)	O3—C13—C14—C15	177.59 (9)
C6—C7—C8—C9	165.49 (9)	C12—C13—C14—C15	−2.08 (14)
C7—C8—C9—C10	−177.79 (9)	C13—C14—C15—C10	−1.68 (14)
C8—C9—C10—C15	−20.71 (16)	C11—C10—C15—C14	3.11 (14)
C8—C9—C10—C11	160.42 (10)	C9—C10—C15—C14	−175.75 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.42	2.786 (1)	103
C17—H17C···Cg1^i	0.96	2.75	3.384 (1)	124

Symmetry code: (i) −x+1, −y, z+1.