N,N′-(Methyl­enedi-p-phenyl­ene)bis­(pyridine-2-carboxamide)

Meghdadi, S.; Khavasi, H.R.; Nalchigar, S.

doi:10.1107/S1600536806046344

N,N′-(Methylenedi-p-phenylene)bis(pyridine-2-carboxamide)

S. Meghdadi, H. R. Khavasi and S. Nalchigar

In the crystal structure of the title compound, C₂₅H₂₀N₄O₂, intramolecular N—H

N and intermolecular N—H

O hydrogen bonds may be effective in its stabilization.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046344/hk2155sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046344/hk2155Isup2.hkl Contains datablock I

CCDC reference: 629921

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.103
Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C25 H20 N4 O2

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

   0 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
   0 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-(Methylenedi-p-phenylene)bis(pyridine-2-carboxamide) top

Crystal data top

C₂₅H₂₀N₄O₂	Z = 2
M_r = 408.45	F(000) = 428
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.719 (3) Å	Cell parameters from 2362 reflections
b = 9.877 (3) Å	θ = 1.7–26.8°
c = 12.444 (4) Å	µ = 0.09 mm⁻¹
α = 100.89 (2)°	T = 297 K
β = 100.12 (3)°	Prism, colorless
γ = 102.54 (2)°	0.45 × 0.4 × 0.15 mm
V = 1000.6 (6) Å³

Data collection top

Stoe IPDS-II diffractometer	3313 reflections with I > 2σ(I)
φ scans	R_int = 0.028
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005)	θ_max = 26.8°, θ_min = 1.7°
T_min = 0.965, T_max = 0.987	h = −9→11
9143 measured reflections	k = −12→12
4198 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0415P)² + 0.1595P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.103	(Δ/σ)_max = 0.002
S = 1.07	Δρ_max = 0.13 e Å⁻³
4198 reflections	Δρ_min = −0.13 e Å⁻³
360 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1080 (2)	1.3815 (2)	0.07782 (17)	0.0690 (5)
H1	0.108 (2)	1.430 (2)	0.0175 (16)	0.079 (6)*
C2	0.0579 (2)	1.4329 (2)	0.17315 (16)	0.0656 (4)
H2	0.029 (2)	1.519 (2)	0.1814 (14)	0.071 (5)*
C3	0.0603 (2)	1.35834 (19)	0.25510 (15)	0.0651 (4)
H3	0.028 (2)	1.398 (2)	0.3239 (17)	0.087 (6)*
C4	0.1113 (2)	1.23459 (18)	0.24005 (14)	0.0588 (4)
H4	0.114 (2)	1.178 (2)	0.2971 (17)	0.086 (6)*
C5	0.15671 (16)	1.18984 (15)	0.14140 (11)	0.0466 (3)
C6	0.20875 (17)	1.05325 (15)	0.12041 (11)	0.0470 (3)
C7	0.29605 (16)	0.90374 (14)	−0.03022 (11)	0.0434 (3)
C8	0.3300 (2)	0.80004 (16)	0.02484 (12)	0.0539 (4)
H8	0.317 (2)	0.8070 (18)	0.1010 (15)	0.066 (5)*
C9	0.37855 (19)	0.68780 (16)	−0.03132 (13)	0.0538 (4)
H9	0.401 (2)	0.6137 (18)	0.0067 (14)	0.063 (5)*
C10	0.39467 (16)	0.67430 (15)	−0.14126 (11)	0.0457 (3)
C11	0.36174 (19)	0.77994 (16)	−0.19433 (12)	0.0507 (3)
H11	0.373 (2)	0.7758 (18)	−0.2734 (15)	0.065 (5)*
C12	0.31310 (18)	0.89254 (16)	−0.14014 (12)	0.0492 (3)
H12	0.2881 (19)	0.9650 (17)	−0.1778 (13)	0.060 (4)*
C13	0.43740 (18)	0.54558 (16)	−0.20300 (14)	0.0525 (4)
H13A	0.510 (2)	0.5114 (17)	−0.1483 (14)	0.062 (5)*
H13B	0.4967 (19)	0.5730 (17)	−0.2616 (14)	0.059 (4)*
C14	0.28903 (17)	0.42400 (14)	−0.26063 (12)	0.0458 (3)
C15	0.23170 (19)	0.31920 (16)	−0.20659 (13)	0.0513 (3)
H15	0.289 (2)	0.3202 (17)	−0.1301 (14)	0.062 (5)*
C16	0.09520 (18)	0.20925 (16)	−0.25794 (12)	0.0502 (3)
H16	0.058 (2)	0.1372 (18)	−0.2188 (14)	0.065 (5)*
C17	0.01122 (17)	0.20068 (14)	−0.36573 (11)	0.0432 (3)
C18	0.0648 (2)	0.30631 (17)	−0.42016 (12)	0.0541 (4)
H18	0.004 (2)	0.3027 (18)	−0.4960 (15)	0.067 (5)*
C19	0.2023 (2)	0.41558 (17)	−0.36683 (13)	0.0549 (4)
H19	0.238 (2)	0.4889 (18)	−0.4080 (14)	0.068 (5)*
C20	−0.21624 (18)	0.04576 (15)	−0.51995 (11)	0.0484 (3)
C21	−0.35287 (17)	−0.08645 (15)	−0.54245 (11)	0.0461 (3)
C22	−0.4720 (2)	−0.12313 (19)	−0.63983 (13)	0.0573 (4)
H22	−0.469 (2)	−0.0638 (19)	−0.6904 (15)	0.067 (5)*
C23	−0.5964 (2)	−0.2440 (2)	−0.65708 (15)	0.0657 (4)
H23	−0.686 (2)	−0.274 (2)	−0.7221 (17)	0.086 (6)*
C24	−0.5968 (2)	−0.3235 (2)	−0.57829 (15)	0.0666 (5)
H24	−0.678 (2)	−0.409 (2)	−0.5876 (16)	0.086 (6)*
C25	−0.4728 (2)	−0.27823 (19)	−0.48338 (15)	0.0656 (4)
H25	−0.472 (2)	−0.334 (2)	−0.4259 (16)	0.077 (5)*
N1	0.15593 (16)	1.26133 (14)	0.06017 (11)	0.0578 (3)
N2	0.24555 (15)	1.02137 (13)	0.01921 (10)	0.0491 (3)
H2B	0.236 (2)	1.0882 (19)	−0.0194 (14)	0.065 (5)*
N3	−0.12479 (15)	0.08417 (13)	−0.41376 (10)	0.0473 (3)
H3B	−0.1588 (19)	0.0254 (18)	−0.3687 (14)	0.060 (5)*
N4	−0.35203 (16)	−0.16190 (14)	−0.46405 (10)	0.0553 (3)
O1	0.21417 (15)	0.98062 (12)	0.18989 (9)	0.0651 (3)
O2	−0.19493 (15)	0.10981 (13)	−0.59318 (9)	0.0717 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0717 (11)	0.0732 (11)	0.0751 (12)	0.0319 (9)	0.0177 (9)	0.0322 (10)
C2	0.0570 (10)	0.0615 (10)	0.0776 (12)	0.0243 (8)	0.0084 (8)	0.0108 (9)
C3	0.0668 (11)	0.0675 (11)	0.0578 (10)	0.0210 (9)	0.0123 (8)	0.0050 (8)
C4	0.0677 (10)	0.0592 (9)	0.0500 (8)	0.0177 (8)	0.0140 (7)	0.0117 (7)
C5	0.0405 (7)	0.0480 (8)	0.0456 (7)	0.0054 (6)	0.0043 (6)	0.0096 (6)
C6	0.0474 (8)	0.0468 (7)	0.0416 (7)	0.0031 (6)	0.0071 (6)	0.0110 (6)
C7	0.0444 (7)	0.0415 (7)	0.0395 (7)	0.0040 (6)	0.0053 (5)	0.0103 (5)
C8	0.0691 (10)	0.0541 (8)	0.0393 (7)	0.0143 (7)	0.0099 (7)	0.0166 (6)
C9	0.0624 (9)	0.0491 (8)	0.0516 (8)	0.0154 (7)	0.0071 (7)	0.0207 (7)
C10	0.0387 (7)	0.0452 (7)	0.0487 (7)	0.0043 (6)	0.0060 (6)	0.0114 (6)
C11	0.0581 (9)	0.0516 (8)	0.0441 (7)	0.0122 (7)	0.0145 (6)	0.0152 (6)
C12	0.0574 (9)	0.0485 (8)	0.0434 (7)	0.0121 (7)	0.0100 (6)	0.0180 (6)
C13	0.0460 (8)	0.0517 (8)	0.0609 (9)	0.0126 (7)	0.0131 (7)	0.0148 (7)
C14	0.0459 (8)	0.0438 (7)	0.0514 (8)	0.0153 (6)	0.0167 (6)	0.0108 (6)
C15	0.0535 (8)	0.0525 (8)	0.0471 (8)	0.0130 (7)	0.0061 (6)	0.0160 (6)
C16	0.0544 (9)	0.0485 (8)	0.0494 (8)	0.0103 (7)	0.0105 (6)	0.0206 (6)
C17	0.0482 (8)	0.0422 (7)	0.0419 (7)	0.0146 (6)	0.0132 (6)	0.0103 (6)
C18	0.0638 (9)	0.0554 (9)	0.0417 (8)	0.0099 (7)	0.0094 (7)	0.0171 (6)
C19	0.0661 (10)	0.0507 (8)	0.0505 (8)	0.0093 (7)	0.0183 (7)	0.0201 (7)
C20	0.0556 (8)	0.0501 (8)	0.0414 (7)	0.0166 (7)	0.0114 (6)	0.0120 (6)
C21	0.0497 (8)	0.0491 (8)	0.0421 (7)	0.0175 (6)	0.0137 (6)	0.0080 (6)
C22	0.0581 (9)	0.0662 (10)	0.0454 (8)	0.0140 (8)	0.0084 (7)	0.0130 (7)
C23	0.0542 (10)	0.0782 (12)	0.0545 (9)	0.0077 (9)	0.0068 (8)	0.0074 (8)
C24	0.0591 (10)	0.0660 (11)	0.0670 (11)	0.0027 (9)	0.0191 (8)	0.0084 (8)
C25	0.0728 (11)	0.0645 (10)	0.0604 (10)	0.0090 (9)	0.0204 (9)	0.0222 (8)
N1	0.0602 (8)	0.0623 (8)	0.0579 (8)	0.0225 (7)	0.0148 (6)	0.0219 (6)
N2	0.0602 (8)	0.0465 (7)	0.0418 (6)	0.0127 (6)	0.0117 (5)	0.0145 (5)
N3	0.0518 (7)	0.0470 (6)	0.0424 (6)	0.0095 (5)	0.0093 (5)	0.0141 (5)
N4	0.0604 (8)	0.0551 (7)	0.0494 (7)	0.0125 (6)	0.0106 (6)	0.0143 (6)
O1	0.0940 (9)	0.0589 (7)	0.0539 (6)	0.0240 (6)	0.0296 (6)	0.0240 (5)
O2	0.0844 (9)	0.0738 (8)	0.0474 (6)	0.0007 (6)	0.0044 (6)	0.0246 (6)

Geometric parameters (Å, º) top

C1—N1	1.334 (2)	C13—H13B	1.009 (17)
C1—C2	1.381 (3)	C14—C19	1.380 (2)
C1—H1	0.965 (19)	C14—C15	1.389 (2)
C2—C3	1.366 (3)	C15—C16	1.383 (2)
C2—H2	0.929 (18)	C15—H15	0.991 (16)
C3—C4	1.381 (2)	C16—C17	1.388 (2)
C3—H3	0.98 (2)	C16—H16	0.968 (18)
C4—C5	1.379 (2)	C17—C18	1.390 (2)
C4—H4	0.98 (2)	C17—N3	1.4094 (19)
C5—N1	1.3378 (19)	C18—C19	1.390 (2)
C5—C6	1.506 (2)	C18—H18	0.988 (17)
C6—O1	1.2244 (17)	C19—H19	0.992 (18)
C6—N2	1.3505 (19)	C20—O2	1.2213 (17)
C7—C12	1.3881 (19)	C20—N3	1.3546 (19)
C7—C8	1.390 (2)	C20—C21	1.507 (2)
C7—N2	1.4033 (19)	C21—N4	1.3349 (19)
C8—C9	1.382 (2)	C21—C22	1.381 (2)
C8—H8	0.966 (17)	C22—C23	1.381 (2)
C9—C10	1.384 (2)	C22—H22	0.937 (18)
C9—H9	0.979 (17)	C23—C24	1.367 (3)
C10—C11	1.390 (2)	C23—H23	0.97 (2)
C10—C13	1.511 (2)	C24—C25	1.381 (3)
C11—C12	1.376 (2)	C24—H24	0.95 (2)
C11—H11	1.001 (17)	C25—N4	1.330 (2)
C12—H12	0.968 (16)	C25—H25	0.979 (19)
C13—C14	1.518 (2)	N2—H2B	0.896 (18)
C13—H13A	1.005 (17)	N3—H3B	0.919 (17)

N1—C1—C2	123.67 (17)	C19—C14—C13	121.62 (14)
N1—C1—H1	114.9 (11)	C15—C14—C13	121.08 (14)
C2—C1—H1	121.4 (11)	C16—C15—C14	121.41 (14)
C3—C2—C1	118.34 (17)	C16—C15—H15	117.8 (10)
C3—C2—H2	122.1 (11)	C14—C15—H15	120.7 (10)
C1—C2—H2	119.4 (11)	C15—C16—C17	120.61 (14)
C2—C3—C4	119.39 (17)	C15—C16—H16	119.9 (10)
C2—C3—H3	117.8 (12)	C17—C16—H16	119.4 (10)
C4—C3—H3	122.8 (12)	C16—C17—C18	118.79 (14)
C5—C4—C3	118.35 (16)	C16—C17—N3	117.55 (12)
C5—C4—H4	120.1 (12)	C18—C17—N3	123.66 (13)
C3—C4—H4	121.6 (12)	C19—C18—C17	119.50 (14)
N1—C5—C4	123.32 (14)	C19—C18—H18	121.0 (10)
N1—C5—C6	116.71 (13)	C17—C18—H18	119.5 (10)
C4—C5—C6	119.96 (13)	C14—C19—C18	122.41 (14)
O1—C6—N2	125.16 (14)	C14—C19—H19	119.9 (10)
O1—C6—C5	121.59 (13)	C18—C19—H19	117.7 (10)
N2—C6—C5	113.25 (12)	O2—C20—N3	125.00 (14)
C12—C7—C8	119.04 (14)	O2—C20—C21	121.03 (13)
C12—C7—N2	117.26 (13)	N3—C20—C21	113.96 (12)
C8—C7—N2	123.70 (13)	N4—C21—C22	123.28 (15)
C9—C8—C7	119.33 (14)	N4—C21—C20	116.78 (13)
C9—C8—H8	121.5 (10)	C22—C21—C20	119.94 (14)
C7—C8—H8	119.2 (10)	C23—C22—C21	118.37 (16)
C8—C9—C10	122.36 (14)	C23—C22—H22	122.1 (11)
C8—C9—H9	119.6 (10)	C21—C22—H22	119.5 (11)
C10—C9—H9	118.1 (10)	C24—C23—C22	119.22 (17)
C9—C10—C11	117.37 (14)	C24—C23—H23	118.3 (12)
C9—C10—C13	121.20 (13)	C22—C23—H23	122.5 (12)
C11—C10—C13	121.35 (13)	C23—C24—C25	118.30 (18)
C12—C11—C10	121.28 (14)	C23—C24—H24	122.3 (12)
C12—C11—H11	118.3 (10)	C25—C24—H24	119.4 (12)
C10—C11—H11	120.4 (10)	N4—C25—C24	123.88 (17)
C11—C12—C7	120.62 (14)	N4—C25—H25	116.8 (11)
C11—C12—H12	121.2 (9)	C24—C25—H25	119.4 (11)
C7—C12—H12	118.2 (10)	C1—N1—C5	116.91 (14)
C10—C13—C14	112.07 (12)	C6—N2—C7	129.74 (13)
C10—C13—H13A	109.3 (9)	C6—N2—H2B	112.2 (11)
C14—C13—H13A	108.8 (9)	C7—N2—H2B	118.1 (11)
C10—C13—H13B	109.6 (9)	C20—N3—C17	128.40 (13)
C14—C13—H13B	108.6 (9)	C20—N3—H3B	113.9 (10)
H13A—C13—H13B	108.4 (13)	C17—N3—H3B	117.7 (10)
C19—C14—C15	117.25 (14)	C25—N4—C21	116.94 (14)

N1—C1—C2—C3	1.3 (3)	C16—C17—C18—C19	1.4 (2)
C1—C2—C3—C4	−0.3 (3)	N3—C17—C18—C19	−178.65 (14)
C2—C3—C4—C5	−0.7 (3)	C15—C14—C19—C18	−1.2 (2)
C3—C4—C5—N1	1.0 (2)	C13—C14—C19—C18	−178.96 (14)
C3—C4—C5—C6	−178.31 (14)	C17—C18—C19—C14	−0.1 (2)
N1—C5—C6—O1	179.66 (14)	O2—C20—C21—N4	169.72 (14)
C4—C5—C6—O1	−1.0 (2)	N3—C20—C21—N4	−10.74 (18)
N1—C5—C6—N2	−0.96 (18)	O2—C20—C21—C22	−11.1 (2)
C4—C5—C6—N2	178.37 (14)	N3—C20—C21—C22	168.45 (13)
C12—C7—C8—C9	−0.6 (2)	N4—C21—C22—C23	−0.1 (2)
N2—C7—C8—C9	179.79 (14)	C20—C21—C22—C23	−179.26 (14)
C7—C8—C9—C10	−0.1 (2)	C21—C22—C23—C24	−0.5 (3)
C8—C9—C10—C11	0.7 (2)	C22—C23—C24—C25	0.7 (3)
C8—C9—C10—C13	−175.98 (14)	C23—C24—C25—N4	−0.3 (3)
C9—C10—C11—C12	−0.8 (2)	C2—C1—N1—C5	−1.1 (3)
C13—C10—C11—C12	175.91 (14)	C4—C5—N1—C1	−0.1 (2)
C10—C11—C12—C7	0.2 (2)	C6—C5—N1—C1	179.21 (14)
C8—C7—C12—C11	0.5 (2)	O1—C6—N2—C7	0.2 (3)
N2—C7—C12—C11	−179.83 (13)	C5—C6—N2—C7	−179.12 (13)
C9—C10—C13—C14	87.52 (17)	C12—C7—N2—C6	174.91 (14)
C11—C10—C13—C14	−89.05 (17)	C8—C7—N2—C6	−5.4 (2)
C10—C13—C14—C19	85.86 (18)	O2—C20—N3—C17	−0.8 (2)
C10—C13—C14—C15	−91.77 (17)	C21—C20—N3—C17	179.65 (12)
C19—C14—C15—C16	1.3 (2)	C16—C17—N3—C20	−173.37 (14)
C13—C14—C15—C16	179.03 (14)	C18—C17—N3—C20	6.7 (2)
C14—C15—C16—C17	0.0 (2)	C24—C25—N4—C21	−0.3 (3)
C15—C16—C17—C18	−1.4 (2)	C22—C21—N4—C25	0.5 (2)
C15—C16—C17—N3	178.69 (14)	C20—C21—N4—C25	179.69 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.90 (2)	2.125 (19)	2.641 (2)	115.8 (14)
N3—H3B···N4	0.920 (19)	2.187 (14)	2.669 (2)	111.8 (13)
N3—H3B···O1ⁱ	0.920 (19)	2.367 (18)	3.162 (2)	144.6 (14)

Symmetry code: (i) −x, −y+1, −z.

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N,N′-(Methyl­enedi-p-phenyl­ene)bis­(pyridine-2-carboxamide)

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N,N′-(Methylenedi-p-phenylene)bis(pyridine-2-carboxamide)