N-Benzoyl-N-(2-pyridylcarbon­yl)benzamide

The molecule of the title compound, C₂₀H₁₄N₂O₃, a tertiary amine with one 2-pyridylcarbonyl and two benzamide substituents, is shaped like a propeller. In the crystal structure, mol­ecules related by a center of symmetry are linked by C—H...O hydrogen bonds to form dimers. These dimers are linked by two further translationally related C—H...O hydrogen bonds and a C—H...π inter­action, forming chains extending in the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.124
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.115
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13    ..  C       ..       2.90 Ang.
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          C
                    H13    C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          C
                    C13    C
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........          C
                    C13    H13    C

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N-Benzoyl-N-(2-pyridylcarbonyl)benzamide

Crystal data

C20H14N2O3	F(000) = 688
Mr = 330.33	Dx = 1.322 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7354 reflections
a = 7.8824 (6) Å	θ = 2.6–25.9°
b = 7.0027 (4) Å	µ = 0.09 mm^−1
c = 30.166 (2) Å	T = 153 K
β = 94.435 (9)°	Plate, colourless
V = 1660.12 (19) Å^3	0.45 × 0.30 × 0.05 mm
Z = 4

Data collection

Stoe IPDS diffractometer	1753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.115
Graphite monochromator	θmax = 25.9°, θmin = 2.6°
Detector resolution: 0.81Å pixels mm^-1	h = −9→9
φ scans	k = −8→8
12507 measured reflections	l = −36→36
3199 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0595P)^2] where P = (Fo^2 + 2Fc^2)/3
3199 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. ¹H-RMN (DMSO, 400 MHz): δ=8.59 (m, 1H, H⁵), δ=8.07 (ddd, 1H, ³J(3,2)=³J(3,4)=7.84 Hz, ⁴J(3,5)=1.55 Hz, H3), δ=8.05 (dd, 1H, ³J(2,3)=7.84 Hz, ⁴J(2,4)=1.55 Hz, H²), δ=7.89 (dd, 4H, ³J(9,10)=7.81 Hz, ⁴J(9,11)=1.38 Hz, H⁹), δ=7.65–7.70 (m, 3H, H⁴ and H¹¹), δ=7.55 (dd, 4H, 3 J(10,9)=3 J(10,11)= 7.81 Hz, H¹⁰).

¹³C-RMN (DMSO, 400 MHz): δ=173.48 (2 C, C⁷), δ=172.74 (1 C, C⁶), δ=150.15 (1 C, C⁵), δ=149.15 (1 C, C¹), δ=139.27 (1 C, C³), δ=134.76 (2 C, C⁸), δ=133.62 (2 C, C¹¹), δ=130.14 (4 C, C¹⁰), δ=130.05 (4 C, C⁹), δ=129.22 (2 C, C⁴), δ=126.01 (1 C, C²).

ESI MS m/z: 353 ([M+Na]+)

IR (KBR disc, cm^-1): 3431(b,w), 2955(m), 2925(s), 2852(m), 1699(s), 1598(m), 1583(m), 1495(w), 1463(s), 1450(m), 1439(m), 1304(m), 1290(s), 1241(m), 1178(m), 1129(m), 1081(m), 1025(m), 994(w), 973(m), 933(m), 870(m), 780(m), 745(m), 732(m), 712(m), 702(m), 650(m), 618(m), 503(w), 419(w).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.42718 (17)	0.7438 (2)	0.05453 (5)	0.0612 (6)
O2	0.49828 (17)	0.7985 (2)	0.17780 (5)	0.0576 (6)
O3	0.14700 (18)	1.0323 (2)	0.12329 (5)	0.0545 (5)
N1	−0.0115 (2)	0.7092 (3)	0.06989 (6)	0.0540 (7)
N2	0.29835 (18)	0.7532 (2)	0.11995 (5)	0.0403 (5)
C1	0.1267 (2)	0.7429 (3)	0.04727 (6)	0.0387 (6)
C2	0.1171 (3)	0.7659 (3)	0.00166 (7)	0.0491 (7)
C3	−0.0400 (3)	0.7581 (3)	−0.02209 (7)	0.0579 (9)
C4	−0.1807 (3)	0.7260 (4)	0.00080 (9)	0.0621 (9)
C5	−0.1631 (3)	0.7008 (4)	0.04593 (8)	0.0614 (9)
C6	0.2966 (2)	0.7489 (3)	0.07288 (7)	0.0418 (7)
C7	0.4508 (2)	0.7027 (3)	0.14607 (7)	0.0410 (7)
C8	0.5386 (2)	0.5242 (3)	0.13379 (6)	0.0393 (7)
C9	0.4534 (3)	0.3731 (3)	0.11278 (7)	0.0503 (8)
C10	0.5420 (3)	0.2086 (4)	0.10354 (9)	0.0641 (9)
C11	0.7146 (3)	0.1958 (4)	0.11498 (8)	0.0637 (9)
C12	0.7989 (3)	0.3452 (4)	0.13600 (8)	0.0591 (9)
C13	0.7123 (2)	0.5096 (3)	0.14619 (7)	0.0479 (7)
C14	0.1841 (2)	0.8805 (3)	0.14067 (6)	0.0407 (7)
C15	0.1161 (2)	0.8134 (3)	0.18222 (7)	0.0431 (7)
C16	0.1348 (2)	0.6270 (3)	0.19679 (7)	0.0477 (8)
C17	0.0669 (3)	0.5708 (4)	0.23540 (8)	0.0641 (9)
C18	−0.0203 (3)	0.7001 (5)	0.25968 (8)	0.0718 (12)
C19	−0.0401 (3)	0.8849 (5)	0.24536 (8)	0.0727 (10)
C20	0.0282 (3)	0.9426 (4)	0.20681 (7)	0.0591 (9)
H2	0.21730	0.78690	−0.01320	0.0590*
H3	−0.05000	0.77440	−0.05340	0.0700*
H4	−0.29030	0.72140	−0.01460	0.0740*
H5	−0.26210	0.67610	0.06110	0.0740*
H9	0.33480	0.38180	0.10470	0.0600*
H10	0.48350	0.10400	0.08930	0.0770*
H11	0.77490	0.08330	0.10820	0.0760*
H12	0.91780	0.33600	0.14370	0.0710*
H13	0.77070	0.61160	0.16150	0.0570*
H16	0.19460	0.53760	0.18020	0.0570*
H17	0.08010	0.44260	0.24540	0.0770*
H18	−0.06670	0.66070	0.28630	0.0860*
H19	−0.10080	0.97340	0.26200	0.0870*
H20	0.01510	1.07110	0.19710	0.0710*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0401 (8)	0.0901 (14)	0.0549 (9)	0.0078 (8)	0.0142 (7)	0.0104 (8)
O2	0.0455 (8)	0.0626 (11)	0.0626 (10)	0.0054 (7)	−0.0087 (7)	−0.0191 (8)
O3	0.0586 (9)	0.0483 (10)	0.0564 (9)	0.0110 (8)	0.0041 (7)	0.0062 (8)
N1	0.0423 (10)	0.0658 (14)	0.0538 (11)	0.0022 (9)	0.0025 (8)	0.0003 (9)
N2	0.0324 (8)	0.0479 (11)	0.0403 (9)	0.0081 (7)	0.0015 (7)	0.0014 (8)
C1	0.0395 (10)	0.0359 (12)	0.0406 (11)	0.0042 (9)	0.0034 (8)	0.0006 (9)
C2	0.0562 (13)	0.0487 (14)	0.0425 (11)	0.0082 (10)	0.0043 (10)	0.0014 (10)
C3	0.0745 (16)	0.0546 (16)	0.0422 (12)	0.0075 (12)	−0.0111 (11)	0.0014 (10)
C4	0.0553 (14)	0.0595 (17)	0.0676 (16)	0.0025 (12)	−0.0198 (12)	−0.0024 (12)
C5	0.0380 (11)	0.0772 (19)	0.0679 (15)	0.0014 (11)	−0.0033 (10)	0.0015 (13)
C6	0.0405 (11)	0.0431 (13)	0.0421 (11)	0.0045 (9)	0.0055 (9)	0.0033 (9)
C7	0.0327 (10)	0.0467 (14)	0.0432 (11)	0.0000 (9)	0.0004 (8)	0.0001 (10)
C8	0.0333 (10)	0.0422 (13)	0.0421 (11)	0.0028 (9)	0.0019 (8)	0.0043 (9)
C9	0.0421 (11)	0.0463 (15)	0.0617 (13)	−0.0035 (10)	−0.0009 (10)	−0.0041 (11)
C10	0.0701 (16)	0.0458 (16)	0.0760 (17)	−0.0067 (12)	0.0039 (13)	−0.0066 (12)
C11	0.0672 (16)	0.0494 (16)	0.0762 (17)	0.0168 (13)	0.0165 (13)	0.0039 (13)
C12	0.0455 (13)	0.0573 (17)	0.0748 (16)	0.0131 (12)	0.0063 (11)	0.0054 (13)
C13	0.0348 (10)	0.0500 (14)	0.0584 (13)	0.0024 (10)	−0.0001 (9)	0.0023 (11)
C14	0.0334 (10)	0.0452 (14)	0.0427 (11)	0.0023 (9)	−0.0023 (8)	−0.0010 (10)
C15	0.0357 (10)	0.0525 (15)	0.0408 (11)	0.0038 (9)	0.0004 (8)	0.0006 (10)
C16	0.0437 (11)	0.0511 (15)	0.0483 (13)	0.0072 (10)	0.0040 (9)	0.0035 (10)
C17	0.0643 (15)	0.0708 (19)	0.0571 (15)	0.0001 (13)	0.0036 (12)	0.0153 (13)
C18	0.0664 (16)	0.104 (3)	0.0462 (14)	0.0022 (16)	0.0114 (12)	0.0123 (14)
C19	0.0720 (17)	0.096 (2)	0.0525 (15)	0.0195 (15)	0.0198 (12)	−0.0059 (15)
C20	0.0617 (14)	0.0644 (17)	0.0518 (14)	0.0184 (12)	0.0074 (11)	−0.0016 (12)

Geometric parameters (Å, º)

O1—C6	1.206 (2)	C15—C16	1.382 (3)
O2—C7	1.205 (3)	C15—C20	1.389 (3)
O3—C14	1.211 (2)	C16—C17	1.376 (3)
N1—C1	1.350 (2)	C17—C18	1.381 (4)
N1—C5	1.349 (3)	C18—C19	1.369 (5)
N2—C6	1.419 (3)	C19—C20	1.379 (3)
N2—C7	1.430 (2)	C2—H2	0.9500
N2—C14	1.443 (2)	C3—H3	0.9500
C1—C2	1.382 (3)	C4—H4	0.9500
C1—C6	1.494 (2)	C5—H5	0.9500
C2—C3	1.383 (3)	C9—H9	0.9500
C3—C4	1.370 (3)	C10—H10	0.9500
C4—C5	1.369 (4)	C11—H11	0.9500
C7—C8	1.489 (3)	C12—H12	0.9500
C8—C9	1.381 (3)	C13—H13	0.9500
C8—C13	1.395 (2)	C16—H16	0.9500
C9—C10	1.387 (3)	C17—H17	0.9500
C10—C11	1.380 (3)	C18—H18	0.9500
C11—C12	1.369 (4)	C19—H19	0.9500
C12—C13	1.385 (3)	C20—H20	0.9500
C14—C15	1.478 (3)
O1···C5^i	3.274 (3)	C13···C5^i	3.516 (3)
O1···C8	2.920 (2)	C14···N1	2.805 (3)
O1···C9	3.133 (3)	C15···O2	3.028 (2)
O2···C18^ii	3.383 (4)	C16···C7	3.069 (2)
O2···C16	3.199 (2)	C16···O2	3.199 (2)
O2···C15	3.028 (2)	C17···O2^viii	3.311 (3)
O2···C17^ii	3.311 (3)	C18···O2^viii	3.383 (4)
O3···C1	3.055 (2)	C6···H9	2.7500
O3···N1	2.994 (2)	C6···H10^iii	2.9100
O1···H10^iii	2.7500	C7···H16	2.6100
O1···H5^i	2.4900	C8···H5^i	2.9900
O1···H2	2.5500	C12···H20^ix	3.0800
O2···H13	2.5900	C13···H19^viii	2.9800
O2···H18^ii	2.7900	C13···H5^i	2.8400
O2···H17^ii	2.6400	C15···H13^vii	3.0900
O3···H12^iv	2.8900	C16···H13^vii	2.9800
O3···H20	2.5400	C16···H12^vii	3.0400
O3···H3^v	2.5700	H2···O1	2.5500
N1···O3	2.994 (2)	H3···O3^v	2.5700
N1···N2	2.788 (2)	H5···O1^vii	2.4900
N1···C14	2.805 (3)	H5···C8^vii	2.9900
N2···N1	2.788 (2)	H5···C13^vii	2.8400
N2···H9	2.6600	H9···N2	2.6600
N2···H16	2.5500	H9···C6	2.7500
C1···O3	3.055 (2)	H10···O1^x	2.7500
C2···C3^v	3.452 (3)	H10···C6^x	2.9100
C2···C4^vi	3.483 (4)	H12···O3^ix	2.8900
C2···C4^v	3.595 (4)	H12···C16^i	3.0400
C2···C5^vi	3.599 (3)	H12···H20^ix	2.5400
C3···C2^v	3.452 (3)	H13···O2	2.5900
C4···C2^vi	3.483 (4)	H13···C15^i	3.0900
C4···C2^v	3.595 (4)	H13···C16^i	2.9800
C5···O1^vii	3.274 (3)	H16···N2	2.5500
C5···C13^vii	3.516 (3)	H16···C7	2.6100
C5···C2^vi	3.599 (3)	H17···O2^viii	2.6400
C6···C9	3.110 (3)	H18···O2^viii	2.7900
C7···C16	3.069 (2)	H19···C13^ii	2.9800
C8···O1	2.920 (2)	H20···O3	2.5400
C9···C6	3.110 (3)	H20···C12^iv	3.0800
C9···O1	3.133 (3)	H20···H12^iv	2.5400
C1—N1—C5	116.92 (18)	C16—C17—C18	120.2 (3)
C6—N2—C7	119.27 (14)	C17—C18—C19	120.1 (2)
C6—N2—C14	119.22 (14)	C18—C19—C20	120.0 (3)
C7—N2—C14	116.11 (15)	C15—C20—C19	120.2 (3)
N1—C1—C2	122.65 (17)	C1—C2—H2	120.00
N1—C1—C6	118.01 (16)	C3—C2—H2	120.00
C2—C1—C6	119.31 (17)	C2—C3—H3	121.00
C1—C2—C3	119.3 (2)	C4—C3—H3	121.00
C2—C3—C4	118.2 (2)	C3—C4—H4	120.00
C3—C4—C5	119.9 (2)	C5—C4—H4	120.00
N1—C5—C4	123.0 (2)	N1—C5—H5	118.00
O1—C6—N2	121.14 (16)	C4—C5—H5	119.00
O1—C6—C1	121.63 (19)	C8—C9—H9	120.00
N2—C6—C1	117.19 (14)	C10—C9—H9	120.00
O2—C7—N2	119.77 (17)	C9—C10—H10	120.00
O2—C7—C8	122.91 (17)	C11—C10—H10	120.00
N2—C7—C8	117.23 (16)	C10—C11—H11	120.00
C7—C8—C9	122.58 (16)	C12—C11—H11	120.00
C7—C8—C13	117.40 (17)	C11—C12—H12	120.00
C9—C8—C13	119.96 (19)	C13—C12—H12	120.00
C8—C9—C10	119.6 (2)	C8—C13—H13	120.00
C9—C10—C11	120.4 (2)	C12—C13—H13	120.00
C10—C11—C12	120.0 (2)	C15—C16—H16	120.00
C11—C12—C13	120.6 (2)	C17—C16—H16	120.00
C8—C13—C12	119.46 (19)	C16—C17—H17	120.00
O3—C14—N2	119.50 (16)	C18—C17—H17	120.00
O3—C14—C15	123.72 (17)	C17—C18—H18	120.00
N2—C14—C15	116.77 (17)	C19—C18—H18	120.00
C14—C15—C16	122.25 (18)	C18—C19—H19	120.00
C14—C15—C20	118.34 (19)	C20—C19—H19	120.00
C16—C15—C20	119.41 (19)	C15—C20—H20	120.00
C15—C16—C17	120.0 (2)	C19—C20—H20	120.00
C5—N1—C1—C2	−0.8 (3)	O2—C7—C8—C9	149.5 (2)
C5—N1—C1—C6	−178.8 (2)	O2—C7—C8—C13	−27.6 (3)
C1—N1—C5—C4	−0.5 (4)	N2—C7—C8—C9	−26.9 (3)
C7—N2—C6—O1	−15.9 (3)	N2—C7—C8—C13	156.01 (17)
C7—N2—C6—C1	161.62 (17)	C7—C8—C9—C10	−178.0 (2)
C14—N2—C6—O1	137.14 (19)	C13—C8—C9—C10	−1.0 (3)
C14—N2—C6—C1	−45.3 (2)	C7—C8—C13—C12	179.2 (2)
C6—N2—C7—O2	135.76 (19)	C9—C8—C13—C12	2.0 (3)
C6—N2—C7—C8	−47.8 (2)	C8—C9—C10—C11	−0.4 (4)
C14—N2—C7—O2	−18.1 (3)	C9—C10—C11—C12	0.7 (4)
C14—N2—C7—C8	158.35 (16)	C10—C11—C12—C13	0.4 (4)
C6—N2—C14—O3	−32.8 (2)	C11—C12—C13—C8	−1.7 (3)
C6—N2—C14—C15	146.00 (16)	O3—C14—C15—C16	167.61 (18)
C7—N2—C14—O3	121.09 (19)	O3—C14—C15—C20	−11.3 (3)
C7—N2—C14—C15	−60.1 (2)	N2—C14—C15—C16	−11.2 (2)
N1—C1—C2—C3	1.3 (3)	N2—C14—C15—C20	169.91 (17)
C6—C1—C2—C3	179.25 (19)	C14—C15—C16—C17	−179.03 (18)
N1—C1—C6—O1	166.5 (2)	C20—C15—C16—C17	−0.1 (3)
N1—C1—C6—N2	−11.1 (3)	C14—C15—C20—C19	178.8 (2)
C2—C1—C6—O1	−11.6 (3)	C16—C15—C20—C19	−0.2 (3)
C2—C1—C6—N2	170.86 (18)	C15—C16—C17—C18	0.1 (3)
C1—C2—C3—C4	−0.5 (3)	C16—C17—C18—C19	0.2 (4)
C2—C3—C4—C5	−0.6 (4)	C17—C18—C19—C20	−0.5 (4)
C3—C4—C5—N1	1.2 (4)	C18—C19—C20—C15	0.5 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x−1, y+1, z; (v) −x, −y+2, −z; (vi) −x, −y+1, −z; (vii) x−1, y, z; (viii) −x+1/2, y−1/2, −z+1/2; (ix) x+1, y−1, z; (x) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3^v	0.95	2.57	3.433 (3)	151
C5—H5···O1^vii	0.95	2.49	3.274 (3)	140
C16—H16···N2	0.95	2.55	2.877 (2)	101
C13—H13···C^i	0.95	2.90	3.762 (2)	151

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