2-(10-Bromo­anthracen-9-yl)-N-phenyl­aniline

In the title compound, C₂₆H₁₈BrN, the central benzene ring makes dihedral angles with its adjacent anthracene ring system and pendant benzene ring of 87.49 (13) and 62.01 (17)°, respectively. The N—H moiety is sterically blocked from forming a hydrogen bond, but weak C—H...π inter­actions occur in the extended structure.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.129
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as analytical
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N1       --H55      .     Please Check
PLAT767_ALERT_4_C INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note
                1  0  0,   1  1  0,   2  0  0,  -1  1  1,   0  1  1,  -2  0  2,
               -1  0  2,   0  0  2,   1  0  2,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
                1  2  0,   2  1  0,   1  1  1,   2  1  1,   3  1  1,  -1  1  2,
                2  2  2,   1  1  3,  -2  0  4,
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note
                2  1  0,   2  2  2,   1  1  3,  -2  0  4,

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..        C11 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.0 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       4.30 Note
              Predicted wR2: Based on SigI   2  3.01 or SHELX Weight 12.78       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   4 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
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

2-(10-Bromoanthracen-9-yl)-N-phenylaniline

Crystal data

C26H18BrN	F(000) = 864
Mr = 424.32	Dx = 1.432 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0619 (17) Å	Cell parameters from 3999 reflections
b = 7.6891 (10) Å	θ = 3.4–26.4°
c = 20.475 (3) Å	µ = 2.10 mm^−1
β = 106.809 (14)°	T = 293 K
V = 1968.6 (5) Å^3	Plate, yellow
Z = 4	0.48 × 0.39 × 0.30 mm

Data collection

Agilent Xcalibur, Atlas, Gemini diffractometer	3115 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
ω scans	θmax = 26.4°, θmin = 3.4°
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	h = −16→14
Tmin = 0.432, Tmax = 0.572	k = −9→8
12046 measured reflections	l = −25→25
3999 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0558P)^2 + 1.6534P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3999 reflections	Δρmax = 0.81 e Å^−3
257 parameters	Δρmin = −1.40 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.

Refinement. The N-bound hydrogen atom was located in a difference map and its position was freely refined. The remaining hydrogen atoms were positioned geometrically [C—H = 0.93 Å] and were refined using a riding model, with U_iso(H) = 1.2 or 1.5U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	−0.02528 (3)	−0.04566 (6)	0.34351 (2)	0.0715 (2)
N1	0.4598 (2)	0.3135 (4)	0.41519 (18)	0.0577 (9)
C3	0.1079 (2)	0.2407 (4)	0.40118 (14)	0.0324 (6)
C12	0.1886 (2)	0.3680 (4)	0.40287 (14)	0.0315 (6)
C11	0.2396 (2)	0.3735 (4)	0.35115 (14)	0.0309 (6)
C5	0.1305 (2)	0.1255 (4)	0.29426 (14)	0.0321 (6)
C10	0.2127 (2)	0.2523 (4)	0.29757 (14)	0.0306 (6)
C4	0.0816 (2)	0.1236 (4)	0.34678 (15)	0.0346 (6)
C15	0.3228 (2)	0.5092 (4)	0.35332 (15)	0.0338 (6)
C9	0.2637 (2)	0.2517 (4)	0.24464 (15)	0.0396 (7)
H9	0.317747	0.331703	0.246104	0.048*
C20	0.4302 (2)	0.4749 (4)	0.38369 (16)	0.0374 (7)
C2	0.0601 (3)	0.2382 (4)	0.45579 (15)	0.0424 (7)
H2	0.007271	0.156905	0.455513	0.051*
C8	0.2351 (3)	0.1373 (4)	0.19247 (16)	0.0467 (8)
H8	0.269377	0.139879	0.158491	0.056*
C21	0.5558 (2)	0.2265 (4)	0.41906 (17)	0.0410 (7)
C13	0.2159 (3)	0.4878 (4)	0.45853 (16)	0.0426 (7)
H13	0.267045	0.573083	0.460148	0.051*
C6	0.1034 (3)	0.0083 (4)	0.23773 (16)	0.0426 (7)
H6	0.049834	−0.073800	0.234413	0.051*
C7	0.1544 (3)	0.0148 (4)	0.18900 (17)	0.0487 (8)
H7	0.135678	−0.063095	0.152715	0.058*
C16	0.2937 (3)	0.6726 (4)	0.32505 (18)	0.0478 (8)
H16	0.221626	0.697953	0.305740	0.057*
C26	0.6048 (3)	0.1311 (4)	0.47645 (18)	0.0482 (8)
H26	0.576252	0.129337	0.513136	0.058*
C18	0.4752 (3)	0.7621 (4)	0.35375 (18)	0.0501 (8)
H18	0.526590	0.845360	0.353300	0.060*
C1	0.0911 (3)	0.3530 (5)	0.50787 (16)	0.0484 (8)
H1	0.060381	0.347710	0.543532	0.058*
C19	0.5059 (3)	0.6027 (4)	0.38339 (19)	0.0492 (8)
H19	0.578117	0.579804	0.403488	0.059*
C22	0.6002 (3)	0.2280 (5)	0.36512 (19)	0.0512 (8)
H22	0.567577	0.291351	0.325915	0.061*
C17	0.3693 (3)	0.7984 (4)	0.32496 (19)	0.0545 (9)
H17	0.348321	0.906707	0.305481	0.065*
C14	0.1681 (3)	0.4789 (5)	0.50894 (17)	0.0497 (8)
H14	0.187045	0.558049	0.544786	0.060*
C23	0.6920 (3)	0.1364 (5)	0.3695 (2)	0.0620 (10)
H23	0.721646	0.139989	0.333358	0.074*
C25	0.6966 (3)	0.0379 (5)	0.4793 (3)	0.0678 (12)
H25	0.729331	−0.027472	0.517943	0.081*
C24	0.7402 (3)	0.0409 (5)	0.4254 (3)	0.0717 (12)
H24	0.801947	−0.021919	0.427468	0.086*
H55	0.425 (3)	0.265 (6)	0.435 (2)	0.073 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0704 (3)	0.0804 (3)	0.0719 (3)	−0.0470 (2)	0.0336 (2)	−0.0247 (2)
N1	0.0311 (15)	0.0545 (18)	0.092 (2)	0.0093 (13)	0.0244 (16)	0.0365 (17)
C3	0.0271 (14)	0.0351 (15)	0.0330 (15)	0.0021 (11)	0.0057 (11)	0.0035 (12)
C12	0.0279 (14)	0.0333 (14)	0.0306 (15)	0.0019 (11)	0.0041 (11)	0.0025 (11)
C11	0.0212 (13)	0.0327 (14)	0.0357 (15)	0.0024 (11)	0.0036 (11)	0.0057 (12)
C5	0.0284 (14)	0.0309 (14)	0.0329 (15)	0.0031 (11)	0.0024 (12)	0.0014 (11)
C10	0.0255 (13)	0.0326 (14)	0.0314 (14)	0.0047 (11)	0.0047 (11)	0.0053 (11)
C4	0.0260 (14)	0.0365 (15)	0.0378 (16)	−0.0035 (12)	0.0039 (12)	0.0021 (12)
C15	0.0315 (15)	0.0330 (14)	0.0371 (16)	−0.0015 (12)	0.0103 (13)	0.0024 (12)
C9	0.0374 (16)	0.0413 (17)	0.0415 (17)	0.0049 (13)	0.0136 (14)	0.0070 (13)
C20	0.0315 (15)	0.0360 (15)	0.0465 (18)	0.0015 (12)	0.0140 (13)	0.0089 (13)
C2	0.0389 (17)	0.0494 (18)	0.0401 (17)	−0.0023 (14)	0.0133 (14)	0.0030 (14)
C8	0.052 (2)	0.054 (2)	0.0379 (17)	0.0078 (16)	0.0188 (15)	0.0020 (15)
C21	0.0286 (15)	0.0322 (15)	0.059 (2)	−0.0012 (12)	0.0069 (14)	0.0050 (14)
C13	0.0433 (18)	0.0419 (17)	0.0410 (18)	−0.0080 (14)	0.0098 (14)	−0.0061 (13)
C6	0.0469 (18)	0.0389 (16)	0.0379 (17)	−0.0039 (14)	0.0059 (14)	−0.0037 (13)
C7	0.062 (2)	0.0439 (18)	0.0373 (18)	0.0047 (16)	0.0093 (16)	−0.0058 (14)
C16	0.0389 (17)	0.0378 (17)	0.061 (2)	0.0031 (14)	0.0050 (15)	0.0133 (15)
C26	0.0388 (17)	0.0457 (18)	0.056 (2)	0.0000 (14)	0.0074 (15)	0.0072 (16)
C18	0.051 (2)	0.0384 (18)	0.065 (2)	−0.0136 (15)	0.0232 (18)	0.0003 (15)
C1	0.0504 (19)	0.060 (2)	0.0377 (18)	0.0041 (16)	0.0181 (15)	−0.0013 (15)
C19	0.0313 (16)	0.0508 (19)	0.066 (2)	−0.0044 (14)	0.0145 (16)	0.0070 (17)
C22	0.049 (2)	0.0476 (19)	0.056 (2)	−0.0016 (16)	0.0134 (17)	0.0038 (16)
C17	0.060 (2)	0.0309 (16)	0.070 (2)	−0.0027 (15)	0.0140 (19)	0.0133 (16)
C14	0.057 (2)	0.054 (2)	0.0386 (18)	−0.0039 (16)	0.0151 (16)	−0.0098 (15)
C23	0.065 (2)	0.045 (2)	0.090 (3)	−0.0036 (18)	0.043 (2)	−0.009 (2)
C25	0.045 (2)	0.052 (2)	0.095 (3)	0.0124 (17)	0.002 (2)	0.024 (2)
C24	0.048 (2)	0.052 (2)	0.121 (4)	0.0122 (18)	0.035 (3)	0.006 (2)

Geometric parameters (Å, º)

Br1—C4	1.896 (3)	C21—C22	1.388 (5)
N1—C20	1.401 (4)	C13—C14	1.353 (5)
N1—C21	1.404 (4)	C13—H13	0.9300
N1—H55	0.78 (4)	C6—C7	1.352 (5)
C3—C4	1.396 (4)	C6—H6	0.9300
C3—C2	1.430 (4)	C7—H7	0.9300
C3—C12	1.432 (4)	C16—C17	1.383 (5)
C12—C11	1.405 (4)	C16—H16	0.9300
C12—C13	1.429 (4)	C26—C25	1.385 (5)
C11—C10	1.405 (4)	C26—H26	0.9300
C11—C15	1.497 (4)	C18—C17	1.366 (5)
C5—C4	1.400 (4)	C18—C19	1.375 (5)
C5—C6	1.428 (4)	C18—H18	0.9300
C5—C10	1.437 (4)	C1—C14	1.392 (5)
C10—C9	1.427 (4)	C1—H1	0.9300
C15—C20	1.386 (4)	C19—H19	0.9300
C15—C16	1.390 (4)	C22—C23	1.371 (5)
C9—C8	1.351 (5)	C22—H22	0.9300
C9—H9	0.9300	C17—H17	0.9300
C20—C19	1.395 (4)	C14—H14	0.9300
C2—C1	1.353 (4)	C23—C24	1.352 (6)
C2—H2	0.9300	C23—H23	0.9300
C8—C7	1.400 (5)	C25—C24	1.381 (6)
C8—H8	0.9300	C25—H25	0.9300
C21—C26	1.376 (5)	C24—H24	0.9300
C20—N1—C21	124.8 (3)	C12—C13—H13	119.6
C20—N1—H55	122 (3)	C7—C6—C5	121.0 (3)
C21—N1—H55	113 (3)	C7—C6—H6	119.5
C4—C3—C2	123.6 (3)	C5—C6—H6	119.5
C4—C3—C12	118.0 (2)	C6—C7—C8	120.8 (3)
C2—C3—C12	118.4 (3)	C6—C7—H7	119.6
C11—C12—C13	121.2 (3)	C8—C7—H7	119.6
C11—C12—C3	120.6 (3)	C17—C16—C15	121.5 (3)
C13—C12—C3	118.2 (3)	C17—C16—H16	119.2
C10—C11—C12	120.1 (2)	C15—C16—H16	119.2
C10—C11—C15	120.1 (2)	C21—C26—C25	119.7 (4)
C12—C11—C15	119.8 (2)	C21—C26—H26	120.2
C4—C5—C6	123.7 (3)	C25—C26—H26	120.2
C4—C5—C10	118.1 (2)	C17—C18—C19	120.2 (3)
C6—C5—C10	118.2 (3)	C17—C18—H18	119.9
C11—C10—C9	121.9 (3)	C19—C18—H18	119.9
C11—C10—C5	120.2 (2)	C2—C1—C14	121.1 (3)
C9—C10—C5	118.0 (3)	C2—C1—H1	119.5
C3—C4—C5	123.0 (3)	C14—C1—H1	119.5
C3—C4—Br1	118.7 (2)	C18—C19—C20	120.8 (3)
C5—C4—Br1	118.3 (2)	C18—C19—H19	119.6
C20—C15—C16	118.6 (3)	C20—C19—H19	119.6
C20—C15—C11	120.8 (3)	C23—C22—C21	120.1 (3)
C16—C15—C11	120.6 (3)	C23—C22—H22	119.9
C8—C9—C10	121.3 (3)	C21—C22—H22	119.9
C8—C9—H9	119.4	C18—C17—C16	119.4 (3)
C10—C9—H9	119.4	C18—C17—H17	120.3
C15—C20—C19	119.4 (3)	C16—C17—H17	120.3
C15—C20—N1	118.9 (3)	C13—C14—C1	120.9 (3)
C19—C20—N1	121.7 (3)	C13—C14—H14	119.5
C1—C2—C3	120.6 (3)	C1—C14—H14	119.5
C1—C2—H2	119.7	C24—C23—C22	121.3 (4)
C3—C2—H2	119.7	C24—C23—H23	119.3
C9—C8—C7	120.7 (3)	C22—C23—H23	119.3
C9—C8—H8	119.6	C24—C25—C26	120.7 (4)
C7—C8—H8	119.6	C24—C25—H25	119.7
C26—C21—C22	119.1 (3)	C26—C25—H25	119.7
C26—C21—N1	119.3 (3)	C23—C24—C25	119.1 (4)
C22—C21—N1	121.5 (3)	C23—C24—H24	120.4
C14—C13—C12	120.8 (3)	C25—C24—H24	120.4
C14—C13—H13	119.6
C4—C3—C12—C11	−0.2 (4)	C11—C15—C20—N1	−2.8 (5)
C2—C3—C12—C11	178.7 (3)	C21—N1—C20—C15	148.5 (3)
C4—C3—C12—C13	−179.9 (3)	C21—N1—C20—C19	−32.9 (5)
C2—C3—C12—C13	−1.0 (4)	C4—C3—C2—C1	178.5 (3)
C13—C12—C11—C10	178.9 (3)	C12—C3—C2—C1	−0.3 (4)
C3—C12—C11—C10	−0.8 (4)	C10—C9—C8—C7	−0.3 (5)
C13—C12—C11—C15	−1.1 (4)	C20—N1—C21—C26	144.7 (4)
C3—C12—C11—C15	179.2 (2)	C20—N1—C21—C22	−38.2 (5)
C12—C11—C10—C9	−179.0 (3)	C11—C12—C13—C14	−178.4 (3)
C15—C11—C10—C9	1.0 (4)	C3—C12—C13—C14	1.3 (5)
C12—C11—C10—C5	1.9 (4)	C4—C5—C6—C7	−179.1 (3)
C15—C11—C10—C5	−178.1 (2)	C10—C5—C6—C7	0.8 (4)
C4—C5—C10—C11	−2.0 (4)	C5—C6—C7—C8	−0.2 (5)
C6—C5—C10—C11	178.1 (3)	C9—C8—C7—C6	0.0 (5)
C4—C5—C10—C9	178.8 (2)	C20—C15—C16—C17	1.9 (5)
C6—C5—C10—C9	−1.0 (4)	C11—C15—C16—C17	−178.4 (3)
C2—C3—C4—C5	−178.8 (3)	C22—C21—C26—C25	−0.4 (5)
C12—C3—C4—C5	0.0 (4)	N1—C21—C26—C25	176.8 (3)
C2—C3—C4—Br1	1.3 (4)	C3—C2—C1—C14	1.6 (5)
C12—C3—C4—Br1	−179.9 (2)	C17—C18—C19—C20	1.0 (5)
C6—C5—C4—C3	−179.1 (3)	C15—C20—C19—C18	0.4 (5)
C10—C5—C4—C3	1.1 (4)	N1—C20—C19—C18	−178.3 (3)
C6—C5—C4—Br1	0.8 (4)	C26—C21—C22—C23	−0.5 (5)
C10—C5—C4—Br1	−179.03 (19)	N1—C21—C22—C23	−177.5 (3)
C10—C11—C15—C20	−86.9 (3)	C19—C18—C17—C16	−0.9 (6)
C12—C11—C15—C20	93.1 (3)	C15—C16—C17—C18	−0.5 (6)
C10—C11—C15—C16	93.3 (4)	C12—C13—C14—C1	−0.1 (5)
C12—C11—C15—C16	−86.7 (4)	C2—C1—C14—C13	−1.3 (5)
C11—C10—C9—C8	−178.3 (3)	C21—C22—C23—C24	1.1 (6)
C5—C10—C9—C8	0.8 (4)	C21—C26—C25—C24	0.6 (6)
C16—C15—C20—C19	−1.8 (5)	C22—C23—C24—C25	−0.9 (6)
C11—C15—C20—C19	178.5 (3)	C26—C25—C24—C23	0.0 (6)
C16—C15—C20—N1	176.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg3^i	0.93	2.77	3.598 (4)	148
C18—H18···Cg5^i	0.93	2.85	3.661 (4)	146

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