N-[4-(Phenyl­ethyn­yl)phen­yl]benzamide

In the title mol­ecule, C₂₁H₁₅NO, the two ethyn­yl-bridged six-membered rings are almost coplanar, making a dihedral angle of 3.3 (2)°. The dihedral angle between the two terminal phen­yl rings is 62.9 (2)°. The crystal packing is stabilized by weak inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.133
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C7     ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C9     ...       1.45 Ang.

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           27.00
           From the CIF: _reflns_number_total               1690
           Count of symmetry unique reflns         1698
           Completeness (_total/calc)             99.53%
           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
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

N-[4-(Phenylethynyl)phenyl]benzamide

Crystal data

C21H15NO	F(000) = 624
Mr = 297.34	Dx = 1.266 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2yc	Cell parameters from 1147 reflections
a = 36.589 (5) Å	θ = 2.2–23.6°
b = 5.3932 (7) Å	µ = 0.08 mm^−1
c = 7.9572 (11) Å	T = 292 K
β = 96.689 (2)°	Block, colourless
V = 1559.5 (4) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1690 independent reflections
Radiation source: fine-focus sealed tube	1360 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −35→46
Tmin = 0.977, Tmax = 0.992	k = −6→6
4343 measured reflections	l = −10→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0786P)^2] where P = (Fo^2 + 2Fc^2)/3
1690 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.21 e Å^−3
2 restraints	Δρmin = −0.24 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
C1	0.44596 (9)	0.2430 (6)	0.7441 (4)	0.0402 (8)
C2	0.47042 (10)	0.0579 (7)	0.7064 (5)	0.0474 (9)
H2	0.4621	−0.0728	0.6359	0.057*
C3	0.50681 (10)	0.0680 (7)	0.7731 (5)	0.0500 (9)
H3	0.5231	−0.0543	0.7462	0.060*
C4	0.51920 (11)	0.2595 (7)	0.8798 (5)	0.0490 (9)
H4	0.5438	0.2660	0.9248	0.059*
C5	0.49531 (11)	0.4401 (8)	0.9196 (5)	0.0521 (10)
H5	0.5037	0.5681	0.9923	0.062*
C6	0.45912 (10)	0.4333 (7)	0.8529 (4)	0.0480 (9)
H6	0.4432	0.5570	0.8805	0.058*
C7	0.40860 (11)	0.2394 (7)	0.6703 (5)	0.0474 (9)
C8	0.37769 (11)	0.2424 (7)	0.6045 (5)	0.0452 (8)
C9	0.33972 (10)	0.2510 (6)	0.5294 (4)	0.0405 (8)
C10	0.32504 (9)	0.0643 (6)	0.4206 (4)	0.0420 (8)
H10	0.3399	−0.0672	0.3953	0.050*
C11	0.28880 (10)	0.0721 (6)	0.3501 (4)	0.0426 (8)
H11	0.2794	−0.0529	0.2770	0.051*
C12	0.26650 (8)	0.2665 (6)	0.3884 (4)	0.0349 (8)
C13	0.28099 (10)	0.4559 (6)	0.4956 (4)	0.0420 (8)
H13	0.2662	0.5887	0.5193	0.050*
C14	0.31707 (10)	0.4464 (6)	0.5660 (4)	0.0432 (8)
H14	0.3265	0.5717	0.6389	0.052*
C15	0.20533 (9)	0.1015 (6)	0.2773 (4)	0.0404 (8)
C16	0.16716 (9)	0.1772 (6)	0.2065 (4)	0.0370 (7)
C17	0.13858 (9)	0.0209 (6)	0.2355 (4)	0.0431 (8)
H17	0.1435	−0.1242	0.2972	0.052*
C18	0.10288 (10)	0.0785 (7)	0.1740 (5)	0.0502 (9)
H18	0.0838	−0.0264	0.1956	0.060*
C19	0.09530 (10)	0.2910 (7)	0.0804 (5)	0.0519 (10)
H19	0.0712	0.3287	0.0380	0.062*
C20	0.12348 (11)	0.4473 (7)	0.0496 (5)	0.0503 (9)
H20	0.1184	0.5904	−0.0141	0.060*
C21	0.15931 (10)	0.3917 (6)	0.1135 (4)	0.0439 (8)
H21	0.1783	0.4989	0.0939	0.053*
N1	0.22924 (8)	0.2895 (5)	0.3170 (3)	0.0397 (7)
H1	0.2211	0.4374	0.2971	0.048*
O1	0.21354 (7)	−0.1174 (4)	0.2992 (4)	0.0605 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (2)	0.0458 (19)	0.0387 (18)	−0.0014 (14)	0.0033 (14)	0.0064 (14)
C2	0.047 (2)	0.046 (2)	0.048 (2)	0.0008 (16)	0.0017 (17)	−0.0048 (16)
C3	0.042 (2)	0.054 (2)	0.053 (2)	0.0115 (16)	0.0032 (16)	0.0029 (17)
C4	0.034 (2)	0.063 (2)	0.048 (2)	−0.0034 (16)	−0.0037 (16)	0.0086 (17)
C5	0.052 (2)	0.050 (2)	0.052 (2)	−0.0096 (17)	−0.0030 (18)	−0.0031 (18)
C6	0.051 (2)	0.045 (2)	0.049 (2)	0.0052 (17)	0.0058 (18)	−0.0020 (16)
C7	0.042 (2)	0.054 (2)	0.046 (2)	0.0003 (16)	0.0013 (17)	0.0024 (16)
C8	0.036 (2)	0.052 (2)	0.047 (2)	−0.0022 (14)	0.0022 (16)	0.0015 (15)
C9	0.036 (2)	0.0446 (19)	0.0407 (19)	−0.0014 (14)	0.0018 (14)	0.0053 (14)
C10	0.0357 (19)	0.044 (2)	0.0458 (19)	0.0032 (15)	0.0042 (15)	−0.0009 (15)
C11	0.0404 (19)	0.0399 (18)	0.0466 (19)	−0.0015 (15)	0.0011 (16)	−0.0054 (15)
C12	0.0302 (19)	0.0352 (18)	0.039 (2)	−0.0025 (12)	0.0015 (15)	0.0031 (13)
C13	0.041 (2)	0.0343 (18)	0.051 (2)	0.0055 (14)	0.0062 (16)	−0.0050 (15)
C14	0.0417 (19)	0.0408 (19)	0.0454 (19)	−0.0037 (15)	−0.0019 (16)	−0.0053 (15)
C15	0.0362 (17)	0.0385 (19)	0.0462 (19)	0.0001 (14)	0.0032 (14)	0.0027 (15)
C16	0.0347 (18)	0.0380 (17)	0.0376 (18)	−0.0034 (14)	0.0012 (14)	−0.0032 (14)
C17	0.0353 (19)	0.0405 (18)	0.052 (2)	−0.0021 (14)	0.0002 (15)	0.0010 (15)
C18	0.0379 (19)	0.051 (2)	0.061 (2)	−0.0077 (16)	0.0022 (16)	−0.0045 (18)
C19	0.038 (2)	0.059 (2)	0.056 (2)	0.0073 (17)	−0.0055 (17)	−0.0101 (19)
C20	0.057 (2)	0.0403 (18)	0.051 (2)	0.0073 (17)	−0.0054 (18)	0.0000 (16)
C21	0.041 (2)	0.0427 (18)	0.047 (2)	−0.0031 (15)	0.0014 (15)	0.0002 (16)
N1	0.0330 (14)	0.0349 (14)	0.0498 (16)	−0.0005 (11)	−0.0013 (12)	−0.0010 (12)
O1	0.0428 (15)	0.0364 (14)	0.099 (2)	0.0002 (11)	−0.0067 (13)	0.0062 (13)

Geometric parameters (Å, º)

C1—C6	1.392 (5)	C12—C13	1.395 (4)
C1—C2	1.396 (5)	C12—N1	1.420 (4)
C1—C7	1.424 (5)	C13—C14	1.374 (5)
C2—C3	1.376 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.380 (5)	C15—O1	1.226 (4)
C3—H3	0.9300	C15—N1	1.353 (4)
C4—C5	1.370 (6)	C15—C16	1.500 (4)
C4—H4	0.9300	C16—C17	1.383 (5)
C5—C6	1.369 (5)	C16—C21	1.385 (5)
C5—H5	0.9300	C17—C18	1.376 (5)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.190 (5)	C18—C19	1.377 (5)
C8—C9	1.448 (5)	C18—H18	0.9300
C9—C14	1.392 (5)	C19—C20	1.376 (6)
C9—C10	1.394 (5)	C19—H19	0.9300
C10—C11	1.379 (4)	C20—C21	1.383 (5)
C10—H10	0.9300	C20—H20	0.9300
C11—C12	1.384 (5)	C21—H21	0.9300
C11—H11	0.9300	N1—H1	0.8600
C6—C1—C2	118.5 (3)	C13—C12—N1	117.3 (3)
C6—C1—C7	120.8 (3)	C14—C13—C12	120.0 (3)
C2—C1—C7	120.7 (3)	C14—C13—H13	120.0
C3—C2—C1	120.3 (3)	C12—C13—H13	120.0
C3—C2—H2	119.9	C13—C14—C9	120.7 (3)
C1—C2—H2	119.9	C13—C14—H14	119.7
C2—C3—C4	120.1 (4)	C9—C14—H14	119.7
C2—C3—H3	120.0	O1—C15—N1	123.2 (3)
C4—C3—H3	120.0	O1—C15—C16	121.2 (3)
C5—C4—C3	120.1 (4)	N1—C15—C16	115.6 (3)
C5—C4—H4	119.9	C17—C16—C21	119.0 (3)
C3—C4—H4	119.9	C17—C16—C15	117.4 (3)
C6—C5—C4	120.4 (4)	C21—C16—C15	123.7 (3)
C6—C5—H5	119.8	C18—C17—C16	120.5 (3)
C4—C5—H5	119.8	C18—C17—H17	119.7
C5—C6—C1	120.7 (3)	C16—C17—H17	119.7
C5—C6—H6	119.7	C17—C18—C19	120.2 (3)
C1—C6—H6	119.7	C17—C18—H18	119.9
C8—C7—C1	177.7 (4)	C19—C18—H18	119.9
C7—C8—C9	178.0 (4)	C20—C19—C18	119.9 (3)
C14—C9—C10	118.8 (3)	C20—C19—H19	120.1
C14—C9—C8	120.3 (3)	C18—C19—H19	120.1
C10—C9—C8	121.0 (3)	C19—C20—C21	120.0 (3)
C11—C10—C9	120.9 (3)	C19—C20—H20	120.0
C11—C10—H10	119.6	C21—C20—H20	120.0
C9—C10—H10	119.6	C20—C21—C16	120.4 (3)
C10—C11—C12	119.8 (3)	C20—C21—H21	119.8
C10—C11—H11	120.1	C16—C21—H21	119.8
C12—C11—H11	120.1	C15—N1—C12	126.3 (3)
C11—C12—C13	119.9 (3)	C15—N1—H1	116.8
C11—C12—N1	122.8 (3)	C12—N1—H1	116.8
C6—C1—C2—C3	−1.4 (5)	C8—C9—C14—C13	−179.9 (3)
C7—C1—C2—C3	177.5 (4)	O1—C15—C16—C17	27.9 (5)
C1—C2—C3—C4	1.0 (5)	N1—C15—C16—C17	−151.0 (3)
C2—C3—C4—C5	0.0 (6)	O1—C15—C16—C21	−151.5 (4)
C3—C4—C5—C6	−0.5 (6)	N1—C15—C16—C21	29.7 (5)
C4—C5—C6—C1	0.2 (6)	C21—C16—C17—C18	−0.4 (5)
C2—C1—C6—C5	0.8 (5)	C15—C16—C17—C18	−179.8 (3)
C7—C1—C6—C5	−178.0 (4)	C16—C17—C18—C19	1.0 (5)
C14—C9—C10—C11	0.1 (5)	C17—C18—C19—C20	−0.6 (6)
C8—C9—C10—C11	179.6 (3)	C18—C19—C20—C21	−0.4 (6)
C9—C10—C11—C12	−0.5 (5)	C19—C20—C21—C16	0.9 (5)
C10—C11—C12—C13	1.2 (5)	C17—C16—C21—C20	−0.5 (5)
C10—C11—C12—N1	178.3 (3)	C15—C16—C21—C20	178.8 (3)
C11—C12—C13—C14	−1.5 (5)	O1—C15—N1—C12	−0.1 (5)
N1—C12—C13—C14	−178.8 (3)	C16—C15—N1—C12	178.7 (3)
C12—C13—C14—C9	1.1 (5)	C11—C12—N1—C15	34.5 (5)
C10—C9—C14—C13	−0.4 (5)	C13—C12—N1—C15	−148.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.42	3.250 (4)	163

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