Crystal structure and Hirshfeld surface analysis of (E)-2-(2,4,6-tri­methyl­benzyl­idene)-3,4-di­hydro­naphthalen-1(2H)-one

In the title compound, C—H...O hydrogen bonds and weak C—H...π inter­actions link adjacent mol­ecules into a three-dimensional supra­molecular network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.155
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        40% Check
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.971 Why?
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C9 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C15 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00573 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16      ..O1       .       2.69 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C20 H20 O
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     75.709 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.441 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     12.673 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.535 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.564 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         79 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.64 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C19 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note

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

   3 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
  10 ALERT type 3 Indicator that the structure quality may be low
   4 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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-2-(2,4,6-Trimethylbenzylidene)-3,4-dihydronaphthalen-1(2H)-one

Crystal data

C20H20O	Z = 2
Mr = 276.36	F(000) = 296
Triclinic, P1	Dx = 1.154 Mg m^−3
a = 8.728 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.757 (2) Å	Cell parameters from 12610 reflections
c = 12.094 (3) Å	θ = 2.7–30.2°
α = 77.768 (19)°	µ = 0.07 mm^−1
β = 80.822 (19)°	T = 293 K
γ = 61.929 (18)°	Prism, colorless
V = 795.2 (4) Å^3	0.64 × 0.51 × 0.33 mm

Data collection

Stoe IPDS 2 diffractometer	1102 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.088
rotation method scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
Tmin = 0.956, Tmax = 0.982	k = −10→10
8143 measured reflections	l = −14→14
2726 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.061	w = 1/[σ^2(Fo^2) + (0.0601P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.155	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.25 e Å^−3
2726 reflections	Δρmin = −0.14 e Å^−3
194 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.016 (4)

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	−1.0524 (3)	−0.2385 (4)	−0.7862 (2)	0.0977 (9)
C12	−0.4930 (4)	−0.5186 (5)	−0.8354 (3)	0.0635 (9)
C2	−1.0387 (4)	−0.2214 (4)	−0.5971 (3)	0.0639 (9)
C17	−0.4278 (4)	−0.6907 (5)	−0.8516 (3)	0.0705 (10)
C1	−0.9638 (4)	−0.2867 (5)	−0.7056 (3)	0.0715 (10)
C10	−0.7746 (4)	−0.4083 (4)	−0.7133 (3)	0.0695 (10)
C13	−0.3805 (5)	−0.4437 (5)	−0.8456 (3)	0.0744 (10)
C11	−0.6837 (4)	−0.4120 (4)	−0.8119 (3)	0.0736 (11)
H11	−0.745928	−0.339613	−0.873942	0.088*
C15	−0.1364 (4)	−0.7151 (5)	−0.8870 (3)	0.0711 (10)
C7	−0.9379 (4)	−0.2800 (5)	−0.5040 (3)	0.0743 (10)
C16	−0.2502 (5)	−0.7860 (5)	−0.8766 (3)	0.0762 (11)
H16	−0.206551	−0.902035	−0.886559	0.091*
C14	−0.2038 (5)	−0.5443 (5)	−0.8704 (3)	0.0798 (11)
H14	−0.128920	−0.494447	−0.875919	0.096*
C3	−1.2113 (4)	−0.0905 (5)	−0.5883 (3)	0.0792 (11)
H3	−1.280000	−0.051417	−0.649452	0.095*
C9	−0.7027 (5)	−0.5193 (6)	−0.6044 (3)	0.1051 (15)
H9A	−0.745452	−0.606334	−0.583241	0.126*
H9B	−0.576855	−0.580756	−0.615353	0.126*
C8	−0.7503 (4)	−0.4167 (5)	−0.5111 (3)	0.0951 (13)
H8A	−0.676588	−0.358974	−0.520287	0.114*
H8B	−0.726257	−0.496759	−0.439895	0.114*
C4	−1.2801 (5)	−0.0192 (5)	−0.4895 (4)	0.0909 (13)
H4	−1.394381	0.067973	−0.484398	0.109*
C6	−1.0115 (5)	−0.2062 (6)	−0.4058 (3)	0.0942 (13)
H6	−0.945571	−0.244732	−0.343260	0.113*
C5	−1.1799 (6)	−0.0771 (6)	−0.4000 (4)	0.0988 (14)
H5	−1.226312	−0.028553	−0.333787	0.119*
C20	0.0576 (4)	−0.8225 (6)	−0.9157 (3)	0.1039 (15)
H20A	0.094884	−0.940932	−0.877619	0.156*
H20B	0.121224	−0.772547	−0.891430	0.156*
H20C	0.078722	−0.821651	−0.996162	0.156*
C18	−0.5449 (5)	−0.7765 (5)	−0.8436 (4)	0.1077 (15)
H18A	−0.589023	−0.792507	−0.766309	0.162*
H18B	−0.479794	−0.888378	−0.868695	0.162*
H18C	−0.640231	−0.703345	−0.890605	0.162*
C19	−0.4477 (5)	−0.2554 (5)	−0.8281 (4)	0.1150 (16)
H19A	−0.531484	−0.178397	−0.882365	0.173*
H19B	−0.352349	−0.226633	−0.838182	0.173*
H19C	−0.501571	−0.241994	−0.752796	0.173*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0782 (16)	0.112 (2)	0.088 (2)	−0.0233 (15)	−0.0269 (14)	−0.0175 (16)
C12	0.069 (2)	0.057 (2)	0.060 (2)	−0.0271 (19)	−0.0034 (16)	−0.0044 (18)
C2	0.061 (2)	0.066 (2)	0.066 (2)	−0.0311 (19)	−0.0055 (18)	−0.0045 (19)
C17	0.079 (2)	0.061 (3)	0.073 (3)	−0.032 (2)	−0.0094 (18)	−0.0086 (19)
C1	0.073 (2)	0.071 (3)	0.069 (3)	−0.031 (2)	−0.019 (2)	−0.001 (2)
C10	0.062 (2)	0.070 (3)	0.062 (2)	−0.0218 (19)	−0.0091 (18)	0.0017 (19)
C13	0.082 (3)	0.058 (3)	0.081 (3)	−0.032 (2)	0.0010 (19)	−0.014 (2)
C11	0.072 (2)	0.072 (3)	0.072 (3)	−0.029 (2)	−0.0174 (19)	−0.001 (2)
C15	0.077 (2)	0.070 (3)	0.058 (2)	−0.026 (2)	−0.0030 (18)	−0.012 (2)
C7	0.071 (2)	0.084 (3)	0.067 (2)	−0.037 (2)	−0.005 (2)	−0.006 (2)
C16	0.095 (3)	0.059 (3)	0.069 (2)	−0.028 (2)	−0.010 (2)	−0.0122 (19)
C14	0.082 (3)	0.081 (3)	0.085 (3)	−0.045 (2)	0.0018 (19)	−0.015 (2)
C3	0.069 (2)	0.077 (3)	0.091 (3)	−0.032 (2)	−0.013 (2)	−0.008 (2)
C9	0.092 (3)	0.101 (3)	0.079 (3)	−0.013 (2)	−0.015 (2)	0.003 (3)
C8	0.080 (3)	0.099 (3)	0.081 (3)	−0.018 (2)	−0.024 (2)	−0.003 (3)
C4	0.076 (3)	0.085 (3)	0.102 (3)	−0.030 (2)	0.008 (3)	−0.022 (3)
C6	0.095 (3)	0.109 (3)	0.072 (3)	−0.040 (3)	−0.010 (2)	−0.012 (3)
C5	0.101 (3)	0.107 (4)	0.085 (3)	−0.045 (3)	0.008 (3)	−0.025 (3)
C20	0.076 (3)	0.113 (4)	0.098 (3)	−0.020 (2)	0.003 (2)	−0.030 (3)
C18	0.114 (3)	0.093 (3)	0.141 (4)	−0.065 (3)	−0.010 (3)	−0.023 (3)
C19	0.107 (3)	0.073 (3)	0.172 (5)	−0.044 (2)	0.007 (3)	−0.038 (3)

Geometric parameters (Å, º)

O1—C1	1.218 (4)	C3—C4	1.383 (5)
C12—C17	1.384 (4)	C3—H3	0.9300
C12—C13	1.393 (4)	C9—C8	1.477 (5)
C12—C11	1.491 (4)	C9—H9A	0.9700
C2—C7	1.396 (5)	C9—H9B	0.9700
C2—C3	1.404 (4)	C8—H8A	0.9700
C2—C1	1.473 (4)	C8—H8B	0.9700
C17—C16	1.390 (4)	C4—C5	1.359 (5)
C17—C18	1.510 (5)	C4—H4	0.9300
C1—C10	1.486 (4)	C6—C5	1.371 (5)
C10—C11	1.319 (4)	C6—H6	0.9300
C10—C9	1.490 (5)	C5—H5	0.9300
C13—C14	1.389 (4)	C20—H20A	0.9600
C13—C19	1.519 (5)	C20—H20B	0.9600
C11—H11	0.9300	C20—H20C	0.9600
C15—C14	1.373 (5)	C18—H18A	0.9600
C15—C16	1.377 (5)	C18—H18B	0.9600
C15—C20	1.524 (4)	C18—H18C	0.9600
C7—C6	1.390 (5)	C19—H19A	0.9600
C7—C8	1.508 (5)	C19—H19B	0.9600
C16—H16	0.9300	C19—H19C	0.9600
C14—H14	0.9300
C17—C12—C13	119.7 (3)	C10—C9—H9A	109.0
C17—C12—C11	120.0 (3)	C8—C9—H9B	109.0
C13—C12—C11	120.3 (3)	C10—C9—H9B	109.0
C7—C2—C3	119.0 (3)	H9A—C9—H9B	107.8
C7—C2—C1	121.2 (3)	C9—C8—C7	114.6 (4)
C3—C2—C1	119.8 (4)	C9—C8—H8A	108.6
C12—C17—C16	119.0 (3)	C7—C8—H8A	108.6
C12—C17—C18	121.7 (3)	C9—C8—H8B	108.6
C16—C17—C18	119.3 (4)	C7—C8—H8B	108.6
O1—C1—C2	121.3 (3)	H8A—C8—H8B	107.6
O1—C1—C10	121.8 (3)	C5—C4—C3	119.6 (4)
C2—C1—C10	116.9 (4)	C5—C4—H4	120.2
C11—C10—C1	119.9 (3)	C3—C4—H4	120.2
C11—C10—C9	125.0 (3)	C5—C6—C7	120.9 (4)
C1—C10—C9	115.1 (3)	C5—C6—H6	119.6
C14—C13—C12	119.3 (3)	C7—C6—H6	119.6
C14—C13—C19	119.7 (4)	C4—C5—C6	121.0 (4)
C12—C13—C19	121.1 (3)	C4—C5—H5	119.5
C10—C11—C12	127.7 (3)	C6—C5—H5	119.5
C10—C11—H11	116.2	C15—C20—H20A	109.5
C12—C11—H11	116.2	C15—C20—H20B	109.5
C14—C15—C16	117.6 (3)	H20A—C20—H20B	109.5
C14—C15—C20	121.2 (4)	C15—C20—H20C	109.5
C16—C15—C20	121.2 (4)	H20A—C20—H20C	109.5
C6—C7—C2	118.9 (3)	H20B—C20—H20C	109.5
C6—C7—C8	120.4 (4)	C17—C18—H18A	109.5
C2—C7—C8	120.6 (3)	C17—C18—H18B	109.5
C15—C16—C17	122.4 (4)	H18A—C18—H18B	109.5
C15—C16—H16	118.8	C17—C18—H18C	109.5
C17—C16—H16	118.8	H18A—C18—H18C	109.5
C15—C14—C13	122.0 (4)	H18B—C18—H18C	109.5
C15—C14—H14	119.0	C13—C19—H19A	109.5
C13—C14—H14	119.0	C13—C19—H19B	109.5
C4—C3—C2	120.6 (4)	H19A—C19—H19B	109.5
C4—C3—H3	119.7	C13—C19—H19C	109.5
C2—C3—H3	119.7	H19A—C19—H19C	109.5
C8—C9—C10	112.8 (4)	H19B—C19—H19C	109.5
C8—C9—H9A	109.0
C13—C12—C17—C16	0.7 (5)	C3—C2—C7—C8	−178.2 (3)
C11—C12—C17—C16	178.2 (3)	C1—C2—C7—C8	−2.0 (5)
C13—C12—C17—C18	−178.9 (3)	C14—C15—C16—C17	0.8 (5)
C11—C12—C17—C18	−1.3 (5)	C20—C15—C16—C17	−179.4 (3)
C7—C2—C1—O1	178.4 (4)	C12—C17—C16—C15	−0.7 (5)
C3—C2—C1—O1	−5.3 (5)	C18—C17—C16—C15	178.9 (3)
C7—C2—C1—C10	−3.8 (5)	C16—C15—C14—C13	−1.0 (5)
C3—C2—C1—C10	172.5 (3)	C20—C15—C14—C13	179.2 (3)
O1—C1—C10—C11	27.7 (6)	C12—C13—C14—C15	1.0 (5)
C2—C1—C10—C11	−150.1 (3)	C19—C13—C14—C15	−179.9 (4)
O1—C1—C10—C9	−152.2 (4)	C7—C2—C3—C4	0.7 (5)
C2—C1—C10—C9	30.0 (5)	C1—C2—C3—C4	−175.6 (3)
C17—C12—C13—C14	−0.8 (5)	C11—C10—C9—C8	129.8 (4)
C11—C12—C13—C14	−178.4 (3)	C1—C10—C9—C8	−50.3 (5)
C17—C12—C13—C19	−179.9 (4)	C10—C9—C8—C7	43.9 (5)
C11—C12—C13—C19	2.6 (5)	C6—C7—C8—C9	163.5 (4)
C1—C10—C11—C12	177.2 (3)	C2—C7—C8—C9	−18.7 (6)
C9—C10—C11—C12	−2.9 (7)	C2—C3—C4—C5	−0.4 (6)
C17—C12—C11—C10	83.3 (5)	C2—C7—C6—C5	−0.3 (6)
C13—C12—C11—C10	−99.2 (5)	C8—C7—C6—C5	177.5 (4)
C3—C2—C7—C6	−0.4 (5)	C3—C4—C5—C6	−0.3 (7)
C1—C2—C7—C6	175.9 (3)	C7—C6—C5—C4	0.7 (7)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1^i	0.93	2.69	3.493 (5)	145
C20—H20C···O1^ii	0.96	2.60	3.535 (5)	165
C9—H9A···Cg2^iii	0.97	2.90	3.865 (6)	175

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