Crystal structure and Hirshfeld surface analysis of diethyl 2-[4-(4-fluoro­phen­yl)-2-methyl-4-oxobutan-2-yl]malonate

The title compound was synthesized by reacting diethyl malonate with 1-(4-fluoro­phen­yl)-3-methyl­but-2-en-1-one. In the crystal, the mol­ecules are joined by C—H...O contacts into infinite chains along the b-axis direction with a C(6) graph-set motif.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.104
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   3 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

   6 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

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Diethyl 2-[4-(4-fluorophenyl)-2-methyl-4-oxobutan-2-yl]propanedioate

Crystal data

C18H23FO5	F(000) = 720
Mr = 338.36	Dx = 1.320 Mg m^−3 Dm = 1.32 Mg m^−3 Dm measured by
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3066 (6) Å	Cell parameters from 2274 reflections
b = 11.5182 (9) Å	θ = 5.4–52.6°
c = 20.2701 (17) Å	µ = 0.10 mm^−1
β = 93.673 (2)°	T = 153 K
V = 1702.4 (2) Å^3	Block, colorless
Z = 4	0.22 × 0.13 × 0.10 mm

Data collection

Bruker Kappa DUO APEXII diffractometer	2835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
0.5° φ scans and ω scans	θmax = 27.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2015)	h = −9→9
Tmin = 0.929, Tmax = 0.941	k = −15→15
15690 measured reflections	l = −26→23
4045 independent 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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 0.1543P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4045 reflections	Δρmax = 0.26 e Å^−3
222 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (6)

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
F1	0.81620 (15)	0.89772 (7)	0.46296 (5)	0.0405 (3)
O1	0.74992 (16)	0.35297 (9)	0.46976 (5)	0.0307 (3)
O2	0.42377 (17)	0.28973 (10)	0.24940 (5)	0.0383 (3)
O3	0.45134 (15)	0.40181 (8)	0.34014 (5)	0.0262 (3)
O4	0.56685 (18)	0.04282 (10)	0.28153 (5)	0.0411 (3)
O5	0.45277 (15)	0.05130 (8)	0.38152 (5)	0.0258 (3)
C1	0.8140 (2)	0.78062 (13)	0.45372 (7)	0.0268 (4)
C2	0.8913 (2)	0.73723 (13)	0.39876 (7)	0.0260 (3)
H2	0.9456	0.7873	0.3683	0.031*
C3	0.8875 (2)	0.61769 (12)	0.38918 (7)	0.0221 (3)
H3	0.9381	0.5856	0.3512	0.026*
C4	0.8102 (2)	0.54422 (12)	0.43457 (7)	0.0205 (3)
C5	0.7325 (2)	0.59304 (13)	0.48947 (7)	0.0247 (3)
H5	0.6782	0.5440	0.5204	0.030*
C6	0.7340 (2)	0.71182 (13)	0.49918 (7)	0.0285 (4)
H6	0.6809	0.7451	0.5364	0.034*
C7	0.8023 (2)	0.41483 (13)	0.42581 (7)	0.0217 (3)
C8	0.8624 (2)	0.36640 (12)	0.36098 (7)	0.0224 (3)
H8A	0.9977	0.3724	0.3620	0.027*
H8B	0.8129	0.4183	0.3252	0.027*
C9	0.8105 (2)	0.24080 (12)	0.34080 (7)	0.0223 (3)
C10	0.8648 (2)	0.22647 (14)	0.26926 (7)	0.0294 (4)
H10A	0.9970	0.2395	0.2675	0.044*
H10B	0.7978	0.2830	0.2408	0.044*
H10C	0.8344	0.1477	0.2538	0.044*
C11	0.9171 (2)	0.15246 (13)	0.38520 (8)	0.0331 (4)
H11A	0.8871	0.0736	0.3699	0.050*
H11B	0.8832	0.1616	0.4309	0.050*
H11C	1.0491	0.1659	0.3831	0.050*
C12	0.5999 (2)	0.22011 (12)	0.34749 (7)	0.0218 (3)
H12	0.5754	0.2345	0.3948	0.026*
C13	0.4813 (2)	0.30483 (13)	0.30589 (7)	0.0232 (3)
C14	0.3506 (2)	0.49428 (13)	0.30408 (7)	0.0261 (4)
H14A	0.2225	0.4698	0.2930	0.031*
H14B	0.4089	0.5117	0.2624	0.031*
C15	0.3541 (2)	0.60000 (13)	0.34758 (8)	0.0288 (4)
H15A	0.2984	0.5814	0.3890	0.043*
H15B	0.2848	0.6627	0.3249	0.043*
H15C	0.4812	0.6248	0.3572	0.043*
C16	0.5405 (2)	0.09577 (13)	0.33143 (7)	0.0247 (3)
C17	0.3988 (2)	−0.07089 (12)	0.37518 (7)	0.0285 (4)
H17A	0.5063	−0.1196	0.3666	0.034*
H17B	0.3050	−0.0809	0.3382	0.034*
C18	0.3222 (2)	−0.10521 (13)	0.43942 (8)	0.0325 (4)
H18A	0.4151	−0.0925	0.4757	0.049*
H18B	0.2879	−0.1875	0.4378	0.049*
H18C	0.2137	−0.0580	0.4466	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0591 (7)	0.0204 (5)	0.0428 (6)	0.0001 (4)	0.0096 (5)	−0.0073 (4)
O1	0.0479 (8)	0.0261 (6)	0.0187 (5)	−0.0084 (5)	0.0049 (5)	0.0033 (5)
O2	0.0477 (8)	0.0406 (7)	0.0252 (6)	0.0070 (6)	−0.0085 (5)	−0.0085 (5)
O3	0.0358 (7)	0.0219 (6)	0.0208 (5)	0.0039 (5)	0.0003 (4)	0.0000 (4)
O4	0.0665 (9)	0.0319 (7)	0.0269 (6)	−0.0175 (6)	0.0188 (6)	−0.0121 (5)
O5	0.0378 (7)	0.0175 (5)	0.0227 (5)	−0.0069 (5)	0.0075 (5)	−0.0008 (4)
C1	0.0324 (9)	0.0199 (8)	0.0279 (8)	−0.0001 (6)	−0.0004 (7)	−0.0038 (6)
C2	0.0322 (9)	0.0245 (8)	0.0216 (8)	−0.0043 (6)	0.0038 (6)	0.0014 (6)
C3	0.0236 (8)	0.0250 (8)	0.0178 (7)	−0.0026 (6)	0.0038 (6)	−0.0028 (6)
C4	0.0222 (8)	0.0220 (7)	0.0172 (7)	−0.0023 (6)	−0.0010 (6)	−0.0002 (6)
C5	0.0281 (9)	0.0281 (8)	0.0182 (7)	−0.0042 (6)	0.0031 (6)	−0.0004 (6)
C6	0.0333 (9)	0.0322 (9)	0.0208 (8)	0.0015 (7)	0.0069 (6)	−0.0070 (7)
C7	0.0224 (8)	0.0238 (8)	0.0187 (7)	−0.0034 (6)	−0.0009 (6)	0.0005 (6)
C8	0.0262 (8)	0.0219 (8)	0.0194 (7)	−0.0025 (6)	0.0041 (6)	0.0001 (6)
C9	0.0270 (8)	0.0197 (8)	0.0206 (7)	−0.0008 (6)	0.0048 (6)	−0.0012 (6)
C10	0.0324 (9)	0.0297 (9)	0.0273 (8)	−0.0027 (7)	0.0105 (7)	−0.0068 (7)
C11	0.0372 (10)	0.0239 (8)	0.0376 (9)	0.0034 (7)	−0.0032 (7)	0.0006 (7)
C12	0.0299 (9)	0.0196 (7)	0.0162 (7)	−0.0042 (6)	0.0049 (6)	−0.0007 (6)
C13	0.0244 (8)	0.0244 (8)	0.0213 (8)	−0.0054 (6)	0.0056 (6)	−0.0011 (6)
C14	0.0276 (9)	0.0279 (8)	0.0227 (8)	0.0013 (6)	0.0004 (6)	0.0070 (6)
C15	0.0320 (9)	0.0273 (9)	0.0275 (8)	0.0058 (7)	0.0048 (7)	0.0055 (7)
C16	0.0295 (9)	0.0234 (8)	0.0214 (8)	−0.0037 (6)	0.0036 (6)	−0.0009 (6)
C17	0.0412 (10)	0.0177 (8)	0.0266 (8)	−0.0071 (7)	0.0031 (7)	−0.0024 (6)
C18	0.0450 (11)	0.0229 (8)	0.0302 (9)	−0.0092 (7)	0.0073 (7)	−0.0006 (7)

Geometric parameters (Å, º)

F1—C1	1.3617 (17)	C9—C11	1.537 (2)
O1—C7	1.2212 (17)	C9—C12	1.572 (2)
O2—C13	1.2070 (17)	C10—H10A	0.9800
O3—C13	1.3407 (17)	C10—H10B	0.9800
O3—C14	1.4633 (17)	C10—H10C	0.9800
O4—C16	1.2070 (17)	C11—H11A	0.9800
O5—C16	1.3372 (17)	C11—H11B	0.9800
O5—C17	1.4650 (17)	C11—H11C	0.9800
C1—C6	1.374 (2)	C12—C13	1.523 (2)
C1—C2	1.375 (2)	C12—C16	1.5254 (19)
C2—C3	1.391 (2)	C12—H12	1.0000
C2—H2	0.9500	C14—C15	1.503 (2)
C3—C4	1.396 (2)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.399 (2)	C15—H15A	0.9800
C4—C7	1.502 (2)	C15—H15B	0.9800
C5—C6	1.382 (2)	C15—H15C	0.9800
C5—H5	0.9500	C17—C18	1.503 (2)
C6—H6	0.9500	C17—H17A	0.9900
C7—C8	1.518 (2)	C17—H17B	0.9900
C8—C9	1.5442 (19)	C18—H18A	0.9800
C8—H8A	0.9900	C18—H18B	0.9800
C8—H8B	0.9900	C18—H18C	0.9800
C9—C10	1.537 (2)
C13—O3—C14	116.19 (11)	C9—C11—H11B	109.5
C16—O5—C17	116.16 (11)	H11A—C11—H11B	109.5
F1—C1—C6	118.74 (14)	C9—C11—H11C	109.5
F1—C1—C2	118.01 (14)	H11A—C11—H11C	109.5
C6—C1—C2	123.25 (14)	H11B—C11—H11C	109.5
C1—C2—C3	117.86 (14)	C13—C12—C16	109.85 (12)
C1—C2—H2	121.1	C13—C12—C9	112.35 (12)
C3—C2—H2	121.1	C16—C12—C9	112.98 (12)
C2—C3—C4	120.92 (13)	C13—C12—H12	107.1
C2—C3—H3	119.5	C16—C12—H12	107.1
C4—C3—H3	119.5	C9—C12—H12	107.1
C3—C4—C5	118.84 (13)	O2—C13—O3	123.55 (14)
C3—C4—C7	122.56 (13)	O2—C13—C12	125.75 (14)
C5—C4—C7	118.58 (13)	O3—C13—C12	110.68 (11)
C6—C5—C4	120.75 (14)	O3—C14—C15	107.93 (11)
C6—C5—H5	119.6	O3—C14—H14A	110.1
C4—C5—H5	119.6	C15—C14—H14A	110.1
C1—C6—C5	118.37 (14)	O3—C14—H14B	110.1
C1—C6—H6	120.8	C15—C14—H14B	110.1
C5—C6—H6	120.8	H14A—C14—H14B	108.4
O1—C7—C4	120.29 (13)	C14—C15—H15A	109.5
O1—C7—C8	122.59 (13)	C14—C15—H15B	109.5
C4—C7—C8	117.12 (12)	H15A—C15—H15B	109.5
C7—C8—C9	119.59 (12)	C14—C15—H15C	109.5
C7—C8—H8A	107.4	H15A—C15—H15C	109.5
C9—C8—H8A	107.4	H15B—C15—H15C	109.5
C7—C8—H8B	107.4	O4—C16—O5	123.54 (13)
C9—C8—H8B	107.4	O4—C16—C12	126.51 (14)
H8A—C8—H8B	107.0	O5—C16—C12	109.95 (12)
C10—C9—C11	109.24 (13)	O5—C17—C18	106.84 (12)
C10—C9—C8	106.06 (12)	O5—C17—H17A	110.4
C11—C9—C8	110.99 (12)	C18—C17—H17A	110.4
C10—C9—C12	112.26 (12)	O5—C17—H17B	110.4
C11—C9—C12	108.15 (12)	C18—C17—H17B	110.4
C8—C9—C12	110.15 (12)	H17A—C17—H17B	108.6
C9—C10—H10A	109.5	C17—C18—H18A	109.5
C9—C10—H10B	109.5	C17—C18—H18B	109.5
H10A—C10—H10B	109.5	H18A—C18—H18B	109.5
C9—C10—H10C	109.5	C17—C18—H18C	109.5
H10A—C10—H10C	109.5	H18A—C18—H18C	109.5
H10B—C10—H10C	109.5	H18B—C18—H18C	109.5
C9—C11—H11A	109.5
F1—C1—C2—C3	−179.48 (13)	C11—C9—C12—C13	179.22 (12)
C6—C1—C2—C3	0.1 (2)	C8—C9—C12—C13	57.76 (15)
C1—C2—C3—C4	−1.1 (2)	C10—C9—C12—C16	64.78 (15)
C2—C3—C4—C5	1.4 (2)	C11—C9—C12—C16	−55.81 (15)
C2—C3—C4—C7	179.59 (13)	C8—C9—C12—C16	−177.27 (11)
C3—C4—C5—C6	−0.8 (2)	C14—O3—C13—O2	−3.2 (2)
C7—C4—C5—C6	−179.03 (13)	C14—O3—C13—C12	175.51 (12)
F1—C1—C6—C5	−179.90 (13)	C16—C12—C13—O2	−36.6 (2)
C2—C1—C6—C5	0.6 (2)	C9—C12—C13—O2	90.11 (18)
C4—C5—C6—C1	−0.2 (2)	C16—C12—C13—O3	144.81 (13)
C3—C4—C7—O1	172.84 (14)	C9—C12—C13—O3	−88.52 (15)
C5—C4—C7—O1	−9.0 (2)	C13—O3—C14—C15	−172.32 (13)
C3—C4—C7—C8	−6.9 (2)	C17—O5—C16—O4	4.1 (2)
C5—C4—C7—C8	171.30 (13)	C17—O5—C16—C12	−175.80 (12)
O1—C7—C8—C9	16.5 (2)	C13—C12—C16—O4	72.5 (2)
C4—C7—C8—C9	−163.76 (13)	C9—C12—C16—O4	−53.8 (2)
C7—C8—C9—C10	171.38 (13)	C13—C12—C16—O5	−107.55 (14)
C7—C8—C9—C11	−70.08 (17)	C9—C12—C16—O5	126.14 (13)
C7—C8—C9—C12	49.67 (17)	C16—O5—C17—C18	173.97 (13)
C10—C9—C12—C13	−60.19 (16)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 aromatic ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O4	0.98	2.40	3.057 (2)	124
C11—H11B···O1	0.98	2.55	3.167 (2)	121
C12—H12···O1	1.00	2.36	3.056 (2)	126
C15—H15B···O2^i	0.98	2.54	3.500 (2)	168
C15—H15C···Cg	0.98	2.93	3.836 (2)	154

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