Crystal structure and Hirshfeld surface analysis and energy frameworks of 1-(2,4-di­methyl­phen­yl)-4-(4-meth­oxy­phen­yl)naphthalene

In the title naphthalene derivative, the mean plane of the naphthalene ring system makes dihedral angles of 65.24 (12)° with the di­methyl­phenyl ring and 55.82 (12)° with meth­oxy­phenyl ring. The latter two rings are inclined to each other by 59.28 (14)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.193
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        46% Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00419 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -9.358 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         36 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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

   2 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
   3 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, 2012); cell refinement: APEX2 and SAINT (Bruker, 2012); data reduction: SAINT and XPREP (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

1-(2,4-Dimethylphenyl)-4-(4-methoxyphenyl)naphthalene

Crystal data

C25H22O	Z = 2
Mr = 338.42	F(000) = 360
Triclinic, P1	Dx = 1.223 Mg m^−3
a = 9.1670 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4566 (10) Å	Cell parameters from 19154 reflections
c = 11.2499 (11) Å	θ = 2.3–22.7°
α = 64.707 (4)°	µ = 0.07 mm^−1
β = 71.312 (4)°	T = 296 K
γ = 77.032 (4)°	Block, yellow
V = 918.75 (16) Å^3	0.15 × 0.10 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1777 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
ω and φ scan	θmax = 26.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→11
Tmin = 0.900, Tmax = 0.945	k = −13→13
19120 measured reflections	l = −14→14
3828 independent 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0922P)^2 + 0.0768P] where P = (Fo^2 + 2Fc^2)/3
3828 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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
C1	0.7907 (4)	0.8345 (4)	0.2984 (3)	0.0771 (10)
H1A	0.7017	0.8047	0.2937	0.116*
H1B	0.7750	0.9350	0.2771	0.116*
H1C	0.8053	0.7849	0.3885	0.116*
C2	0.9307 (3)	0.8015 (3)	0.1987 (3)	0.0509 (7)
C3	1.0610 (3)	0.8748 (3)	0.1542 (3)	0.0578 (8)
H3	1.0583	0.9411	0.1898	0.069*
C4	1.1927 (3)	0.8530 (3)	0.0602 (3)	0.0573 (8)
C5	1.3309 (4)	0.9324 (4)	0.0196 (4)	0.0863 (11)
H5A	1.4237	0.8679	0.0169	0.129*
H5B	1.3205	0.9724	0.0848	0.129*
H5C	1.3365	1.0071	−0.0686	0.129*
C6	1.1935 (3)	0.7571 (3)	0.0065 (3)	0.0598 (8)
H6	1.2803	0.7415	−0.0585	0.072*
C7	1.0668 (3)	0.6835 (3)	0.0480 (3)	0.0541 (7)
H7	1.0699	0.6198	0.0093	0.065*
C8	0.9353 (3)	0.7015 (3)	0.1453 (3)	0.0446 (7)
C9	0.8049 (3)	0.6158 (3)	0.1869 (3)	0.0437 (6)
C10	0.7284 (3)	0.6328 (3)	0.0942 (3)	0.0537 (7)
H10	0.7534	0.7037	0.0079	0.064*
C11	0.6138 (3)	0.5472 (3)	0.1247 (3)	0.0527 (7)
H11	0.5648	0.5633	0.0581	0.063*
C12	0.5716 (3)	0.4408 (3)	0.2488 (3)	0.0426 (6)
C13	0.6437 (3)	0.4220 (3)	0.3514 (2)	0.0393 (6)
C14	0.7621 (3)	0.5075 (3)	0.3195 (2)	0.0403 (6)
C15	0.8360 (3)	0.4807 (3)	0.4219 (3)	0.0507 (7)
H15	0.9173	0.5323	0.4017	0.061*
C16	0.7907 (3)	0.3810 (3)	0.5493 (3)	0.0602 (8)
H16	0.8414	0.3649	0.6147	0.072*
C17	0.6690 (3)	0.3029 (3)	0.5823 (3)	0.0612 (8)
H17	0.6361	0.2374	0.6706	0.073*
C18	0.5983 (3)	0.3221 (3)	0.4860 (3)	0.0518 (7)
H18	0.5180	0.2682	0.5092	0.062*
C19	0.4540 (3)	0.3483 (3)	0.2743 (2)	0.0432 (6)
C20	0.3108 (3)	0.4064 (3)	0.2491 (3)	0.0504 (7)
H20	0.2877	0.5046	0.2182	0.060*
C21	0.2007 (3)	0.3235 (3)	0.2682 (3)	0.0525 (7)
H21	0.1051	0.3658	0.2507	0.063*
C22	0.2331 (3)	0.1787 (3)	0.3130 (3)	0.0510 (7)
C23	0.3750 (3)	0.1177 (3)	0.3379 (3)	0.0601 (8)
H23	0.3977	0.0195	0.3676	0.072*
C24	0.4841 (3)	0.2011 (3)	0.3193 (3)	0.0543 (7)
H24	0.5794	0.1581	0.3371	0.065*
C25	−0.0236 (4)	0.1430 (4)	0.3343 (4)	0.0834 (11)
H25A	−0.0854	0.0667	0.3644	0.125*
H25B	−0.0284	0.2070	0.2437	0.125*
H25C	−0.0624	0.1932	0.3942	0.125*
O1	0.1324 (2)	0.0867 (2)	0.3352 (2)	0.0742 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.076 (2)	0.079 (2)	0.081 (2)	−0.0173 (19)	−0.0011 (18)	−0.044 (2)
C2	0.0503 (17)	0.0521 (17)	0.0505 (17)	−0.0106 (14)	−0.0132 (14)	−0.0171 (14)
C3	0.068 (2)	0.0485 (17)	0.0622 (19)	−0.0158 (15)	−0.0235 (16)	−0.0169 (15)
C4	0.0534 (18)	0.0526 (18)	0.0532 (18)	−0.0149 (15)	−0.0173 (15)	−0.0013 (15)
C5	0.069 (2)	0.091 (3)	0.088 (3)	−0.040 (2)	−0.0228 (19)	−0.007 (2)
C6	0.0523 (18)	0.0585 (19)	0.0533 (18)	−0.0127 (15)	−0.0040 (14)	−0.0106 (16)
C7	0.0547 (17)	0.0528 (18)	0.0498 (17)	−0.0128 (14)	−0.0061 (14)	−0.0169 (14)
C8	0.0491 (16)	0.0419 (15)	0.0427 (15)	−0.0124 (13)	−0.0133 (13)	−0.0113 (13)
C9	0.0458 (15)	0.0475 (16)	0.0415 (15)	−0.0104 (13)	−0.0101 (12)	−0.0186 (13)
C10	0.0621 (18)	0.0550 (18)	0.0421 (16)	−0.0192 (15)	−0.0150 (14)	−0.0093 (14)
C11	0.0593 (18)	0.0571 (18)	0.0424 (17)	−0.0159 (15)	−0.0180 (14)	−0.0113 (14)
C12	0.0412 (15)	0.0454 (15)	0.0438 (16)	−0.0070 (12)	−0.0088 (12)	−0.0197 (13)
C13	0.0393 (14)	0.0416 (15)	0.0365 (15)	−0.0044 (12)	−0.0067 (11)	−0.0165 (12)
C14	0.0404 (14)	0.0416 (15)	0.0408 (15)	−0.0055 (12)	−0.0091 (12)	−0.0178 (13)
C15	0.0515 (16)	0.0574 (18)	0.0482 (17)	−0.0131 (14)	−0.0149 (14)	−0.0197 (15)
C16	0.069 (2)	0.070 (2)	0.0467 (18)	−0.0158 (17)	−0.0230 (15)	−0.0174 (16)
C17	0.073 (2)	0.067 (2)	0.0392 (17)	−0.0215 (17)	−0.0110 (15)	−0.0115 (15)
C18	0.0526 (17)	0.0563 (18)	0.0454 (17)	−0.0149 (14)	−0.0063 (13)	−0.0185 (15)
C19	0.0435 (15)	0.0456 (16)	0.0436 (15)	−0.0065 (13)	−0.0088 (12)	−0.0206 (13)
C20	0.0522 (17)	0.0465 (16)	0.0551 (17)	−0.0068 (14)	−0.0183 (13)	−0.0179 (14)
C21	0.0458 (16)	0.0576 (19)	0.0610 (18)	−0.0057 (14)	−0.0174 (13)	−0.0261 (15)
C22	0.0521 (18)	0.0548 (19)	0.0544 (18)	−0.0148 (15)	−0.0075 (14)	−0.0285 (15)
C23	0.060 (2)	0.0463 (17)	0.076 (2)	−0.0056 (16)	−0.0136 (16)	−0.0280 (16)
C24	0.0451 (16)	0.0518 (18)	0.0666 (19)	−0.0019 (14)	−0.0130 (14)	−0.0256 (15)
C25	0.060 (2)	0.102 (3)	0.108 (3)	−0.029 (2)	−0.0172 (19)	−0.051 (2)
O1	0.0641 (14)	0.0687 (14)	0.1023 (18)	−0.0233 (12)	−0.0140 (12)	−0.0415 (13)

Geometric parameters (Å, º)

C1—C2	1.495 (4)	C13—C18	1.413 (3)
C1—H1A	0.9600	C13—C14	1.421 (3)
C1—H1B	0.9600	C14—C15	1.416 (3)
C1—H1C	0.9600	C15—C16	1.360 (4)
C2—C8	1.399 (4)	C15—H15	0.9300
C2—C3	1.401 (3)	C16—C17	1.390 (3)
C3—C4	1.375 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.357 (4)
C4—C6	1.373 (4)	C17—H17	0.9300
C4—C5	1.510 (4)	C18—H18	0.9300
C5—H5A	0.9600	C19—C20	1.380 (4)
C5—H5B	0.9600	C19—C24	1.391 (4)
C5—H5C	0.9600	C20—C21	1.383 (3)
C6—C7	1.381 (3)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.370 (4)
C7—C8	1.385 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—O1	1.373 (3)
C8—C9	1.488 (3)	C22—C23	1.373 (4)
C9—C10	1.366 (3)	C23—C24	1.381 (3)
C9—C14	1.430 (3)	C23—H23	0.9300
C10—C11	1.397 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—O1	1.420 (4)
C11—C12	1.363 (4)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.430 (3)	C25—H25C	0.9600
C12—C19	1.488 (3)
C2—C1—H1A	109.5	C18—C13—C12	121.9 (2)
C2—C1—H1B	109.5	C14—C13—C12	119.8 (2)
H1A—C1—H1B	109.5	C15—C14—C13	118.0 (2)
C2—C1—H1C	109.5	C15—C14—C9	121.8 (2)
H1A—C1—H1C	109.5	C13—C14—C9	120.2 (2)
H1B—C1—H1C	109.5	C16—C15—C14	121.4 (3)
C8—C2—C3	118.4 (2)	C16—C15—H15	119.3
C8—C2—C1	122.1 (2)	C14—C15—H15	119.3
C3—C2—C1	119.5 (3)	C15—C16—C17	120.4 (3)
C4—C3—C2	122.9 (3)	C15—C16—H16	119.8
C4—C3—H3	118.5	C17—C16—H16	119.8
C2—C3—H3	118.5	C18—C17—C16	120.1 (3)
C6—C4—C3	117.8 (3)	C18—C17—H17	120.0
C6—C4—C5	121.9 (3)	C16—C17—H17	120.0
C3—C4—C5	120.3 (3)	C17—C18—C13	121.6 (3)
C4—C5—H5A	109.5	C17—C18—H18	119.2
C4—C5—H5B	109.5	C13—C18—H18	119.2
H5A—C5—H5B	109.5	C20—C19—C24	117.0 (2)
C4—C5—H5C	109.5	C20—C19—C12	120.9 (2)
H5A—C5—H5C	109.5	C24—C19—C12	122.1 (2)
H5B—C5—H5C	109.5	C19—C20—C21	122.2 (3)
C4—C6—C7	120.7 (3)	C19—C20—H20	118.9
C4—C6—H6	119.7	C21—C20—H20	118.9
C7—C6—H6	119.7	C22—C21—C20	119.7 (3)
C6—C7—C8	122.1 (3)	C22—C21—H21	120.2
C6—C7—H7	119.0	C20—C21—H21	120.2
C8—C7—H7	119.0	C21—C22—O1	124.4 (3)
C7—C8—C2	118.1 (2)	C21—C22—C23	119.5 (3)
C7—C8—C9	118.8 (2)	O1—C22—C23	116.0 (3)
C2—C8—C9	123.1 (2)	C22—C23—C24	120.5 (3)
C10—C9—C14	117.6 (2)	C22—C23—H23	119.8
C10—C9—C8	120.0 (2)	C24—C23—H23	119.8
C14—C9—C8	122.3 (2)	C23—C24—C19	121.2 (3)
C9—C10—C11	122.3 (3)	C23—C24—H24	119.4
C9—C10—H10	118.9	C19—C24—H24	119.4
C11—C10—H10	118.9	O1—C25—H25A	109.5
C12—C11—C10	122.1 (3)	O1—C25—H25B	109.5
C12—C11—H11	119.0	H25A—C25—H25B	109.5
C10—C11—H11	119.0	O1—C25—H25C	109.5
C11—C12—C13	118.0 (2)	H25A—C25—H25C	109.5
C11—C12—C19	120.0 (2)	H25B—C25—H25C	109.5
C13—C12—C19	122.0 (2)	C22—O1—C25	117.3 (2)
C18—C13—C14	118.4 (2)
C8—C2—C3—C4	0.2 (4)	C12—C13—C14—C9	2.4 (3)
C1—C2—C3—C4	−178.4 (3)	C10—C9—C14—C15	179.2 (2)
C2—C3—C4—C6	1.4 (4)	C8—C9—C14—C15	3.5 (4)
C2—C3—C4—C5	−178.2 (3)	C10—C9—C14—C13	0.0 (3)
C3—C4—C6—C7	−1.2 (4)	C8—C9—C14—C13	−175.7 (2)
C5—C4—C6—C7	178.4 (3)	C13—C14—C15—C16	−3.2 (4)
C4—C6—C7—C8	−0.7 (4)	C9—C14—C15—C16	177.6 (2)
C6—C7—C8—C2	2.3 (4)	C14—C15—C16—C17	−0.3 (4)
C6—C7—C8—C9	−178.6 (2)	C15—C16—C17—C18	2.4 (4)
C3—C2—C8—C7	−2.0 (4)	C16—C17—C18—C13	−0.9 (4)
C1—C2—C8—C7	176.6 (3)	C14—C13—C18—C17	−2.6 (4)
C3—C2—C8—C9	178.9 (2)	C12—C13—C18—C17	178.8 (3)
C1—C2—C8—C9	−2.5 (4)	C11—C12—C19—C20	−53.8 (3)
C7—C8—C9—C10	−63.5 (3)	C13—C12—C19—C20	126.4 (3)
C2—C8—C9—C10	115.5 (3)	C11—C12—C19—C24	123.9 (3)
C7—C8—C9—C14	112.1 (3)	C13—C12—C19—C24	−56.0 (3)
C2—C8—C9—C14	−68.9 (3)	C24—C19—C20—C21	0.5 (4)
C14—C9—C10—C11	−1.1 (4)	C12—C19—C20—C21	178.2 (2)
C8—C9—C10—C11	174.7 (2)	C19—C20—C21—C22	−0.3 (4)
C9—C10—C11—C12	−0.3 (4)	C20—C21—C22—O1	−179.9 (2)
C10—C11—C12—C13	2.7 (4)	C20—C21—C22—C23	−0.2 (4)
C10—C11—C12—C19	−177.2 (2)	C21—C22—C23—C24	0.6 (4)
C11—C12—C13—C18	174.9 (2)	O1—C22—C23—C24	−179.7 (2)
C19—C12—C13—C18	−5.2 (3)	C22—C23—C24—C19	−0.4 (4)
C11—C12—C13—C14	−3.7 (3)	C20—C19—C24—C23	−0.1 (4)
C19—C12—C13—C14	176.2 (2)	C12—C19—C24—C23	−177.8 (2)
C18—C13—C14—C15	4.5 (3)	C21—C22—O1—C25	−11.4 (4)
C12—C13—C14—C15	−176.8 (2)	C23—C22—O1—C25	168.9 (3)
C18—C13—C14—C9	−176.2 (2)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···Cg^i	0.96	2.78	3.597 (5)	144

Symmetry code: (i) x−1, y, z.