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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046344/hk2155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046344/hk2155Isup2.hkl
Contains datablock I

CCDC reference: 629921

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](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
C25H20N4O2Z = 2
Mr = 408.45F(000) = 428
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.719 (3) ÅCell parameters from 2362 reflections
b = 9.877 (3) Åθ = 1.7–26.8°
c = 12.444 (4) ŵ = 0.09 mm1
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 scansRint = 0.028
Absorption correction: numerical
(X-RED32; Stoe & Cie, 2005)
θmax = 26.8°, θmin = 1.7°
Tmin = 0.965, Tmax = 0.987h = 911
9143 measured reflectionsk = 1212
4198 independent reflectionsl = 1515
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.1595P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.002
S = 1.07Δρmax = 0.13 e Å3
4198 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
C10.1080 (2)1.3815 (2)0.07782 (17)0.0690 (5)
H10.108 (2)1.430 (2)0.0175 (16)0.079 (6)*
C20.0579 (2)1.4329 (2)0.17315 (16)0.0656 (4)
H20.029 (2)1.519 (2)0.1814 (14)0.071 (5)*
C30.0603 (2)1.35834 (19)0.25510 (15)0.0651 (4)
H30.028 (2)1.398 (2)0.3239 (17)0.087 (6)*
C40.1113 (2)1.23459 (18)0.24005 (14)0.0588 (4)
H40.114 (2)1.178 (2)0.2971 (17)0.086 (6)*
C50.15671 (16)1.18984 (15)0.14140 (11)0.0466 (3)
C60.20875 (17)1.05325 (15)0.12041 (11)0.0470 (3)
C70.29605 (16)0.90374 (14)0.03022 (11)0.0434 (3)
C80.3300 (2)0.80004 (16)0.02484 (12)0.0539 (4)
H80.317 (2)0.8070 (18)0.1010 (15)0.066 (5)*
C90.37855 (19)0.68780 (16)0.03132 (13)0.0538 (4)
H90.401 (2)0.6137 (18)0.0067 (14)0.063 (5)*
C100.39467 (16)0.67430 (15)0.14126 (11)0.0457 (3)
C110.36174 (19)0.77994 (16)0.19433 (12)0.0507 (3)
H110.373 (2)0.7758 (18)0.2734 (15)0.065 (5)*
C120.31310 (18)0.89254 (16)0.14014 (12)0.0492 (3)
H120.2881 (19)0.9650 (17)0.1778 (13)0.060 (4)*
C130.43740 (18)0.54558 (16)0.20300 (14)0.0525 (4)
H13A0.510 (2)0.5114 (17)0.1483 (14)0.062 (5)*
H13B0.4967 (19)0.5730 (17)0.2616 (14)0.059 (4)*
C140.28903 (17)0.42400 (14)0.26063 (12)0.0458 (3)
C150.23170 (19)0.31920 (16)0.20659 (13)0.0513 (3)
H150.289 (2)0.3202 (17)0.1301 (14)0.062 (5)*
C160.09520 (18)0.20925 (16)0.25794 (12)0.0502 (3)
H160.058 (2)0.1372 (18)0.2188 (14)0.065 (5)*
C170.01122 (17)0.20068 (14)0.36573 (11)0.0432 (3)
C180.0648 (2)0.30631 (17)0.42016 (12)0.0541 (4)
H180.004 (2)0.3027 (18)0.4960 (15)0.067 (5)*
C190.2023 (2)0.41558 (17)0.36683 (13)0.0549 (4)
H190.238 (2)0.4889 (18)0.4080 (14)0.068 (5)*
C200.21624 (18)0.04576 (15)0.51995 (11)0.0484 (3)
C210.35287 (17)0.08645 (15)0.54245 (11)0.0461 (3)
C220.4720 (2)0.12313 (19)0.63983 (13)0.0573 (4)
H220.469 (2)0.0638 (19)0.6904 (15)0.067 (5)*
C230.5964 (2)0.2440 (2)0.65708 (15)0.0657 (4)
H230.686 (2)0.274 (2)0.7221 (17)0.086 (6)*
C240.5968 (2)0.3235 (2)0.57829 (15)0.0666 (5)
H240.678 (2)0.409 (2)0.5876 (16)0.086 (6)*
C250.4728 (2)0.27823 (19)0.48338 (15)0.0656 (4)
H250.472 (2)0.334 (2)0.4259 (16)0.077 (5)*
N10.15593 (16)1.26133 (14)0.06017 (11)0.0578 (3)
N20.24555 (15)1.02137 (13)0.01921 (10)0.0491 (3)
H2B0.236 (2)1.0882 (19)0.0194 (14)0.065 (5)*
N30.12479 (15)0.08417 (13)0.41376 (10)0.0473 (3)
H3B0.1588 (19)0.0254 (18)0.3687 (14)0.060 (5)*
N40.35203 (16)0.16190 (14)0.46405 (10)0.0553 (3)
O10.21417 (15)0.98062 (12)0.18989 (9)0.0651 (3)
O20.19493 (15)0.10981 (13)0.59318 (9)0.0717 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0717 (11)0.0732 (11)0.0751 (12)0.0319 (9)0.0177 (9)0.0322 (10)
C20.0570 (10)0.0615 (10)0.0776 (12)0.0243 (8)0.0084 (8)0.0108 (9)
C30.0668 (11)0.0675 (11)0.0578 (10)0.0210 (9)0.0123 (8)0.0050 (8)
C40.0677 (10)0.0592 (9)0.0500 (8)0.0177 (8)0.0140 (7)0.0117 (7)
C50.0405 (7)0.0480 (8)0.0456 (7)0.0054 (6)0.0043 (6)0.0096 (6)
C60.0474 (8)0.0468 (7)0.0416 (7)0.0031 (6)0.0071 (6)0.0110 (6)
C70.0444 (7)0.0415 (7)0.0395 (7)0.0040 (6)0.0053 (5)0.0103 (5)
C80.0691 (10)0.0541 (8)0.0393 (7)0.0143 (7)0.0099 (7)0.0166 (6)
C90.0624 (9)0.0491 (8)0.0516 (8)0.0154 (7)0.0071 (7)0.0207 (7)
C100.0387 (7)0.0452 (7)0.0487 (7)0.0043 (6)0.0060 (6)0.0114 (6)
C110.0581 (9)0.0516 (8)0.0441 (7)0.0122 (7)0.0145 (6)0.0152 (6)
C120.0574 (9)0.0485 (8)0.0434 (7)0.0121 (7)0.0100 (6)0.0180 (6)
C130.0460 (8)0.0517 (8)0.0609 (9)0.0126 (7)0.0131 (7)0.0148 (7)
C140.0459 (8)0.0438 (7)0.0514 (8)0.0153 (6)0.0167 (6)0.0108 (6)
C150.0535 (8)0.0525 (8)0.0471 (8)0.0130 (7)0.0061 (6)0.0160 (6)
C160.0544 (9)0.0485 (8)0.0494 (8)0.0103 (7)0.0105 (6)0.0206 (6)
C170.0482 (8)0.0422 (7)0.0419 (7)0.0146 (6)0.0132 (6)0.0103 (6)
C180.0638 (9)0.0554 (9)0.0417 (8)0.0099 (7)0.0094 (7)0.0171 (6)
C190.0661 (10)0.0507 (8)0.0505 (8)0.0093 (7)0.0183 (7)0.0201 (7)
C200.0556 (8)0.0501 (8)0.0414 (7)0.0166 (7)0.0114 (6)0.0120 (6)
C210.0497 (8)0.0491 (8)0.0421 (7)0.0175 (6)0.0137 (6)0.0080 (6)
C220.0581 (9)0.0662 (10)0.0454 (8)0.0140 (8)0.0084 (7)0.0130 (7)
C230.0542 (10)0.0782 (12)0.0545 (9)0.0077 (9)0.0068 (8)0.0074 (8)
C240.0591 (10)0.0660 (11)0.0670 (11)0.0027 (9)0.0191 (8)0.0084 (8)
C250.0728 (11)0.0645 (10)0.0604 (10)0.0090 (9)0.0204 (9)0.0222 (8)
N10.0602 (8)0.0623 (8)0.0579 (8)0.0225 (7)0.0148 (6)0.0219 (6)
N20.0602 (8)0.0465 (7)0.0418 (6)0.0127 (6)0.0117 (5)0.0145 (5)
N30.0518 (7)0.0470 (6)0.0424 (6)0.0095 (5)0.0093 (5)0.0141 (5)
N40.0604 (8)0.0551 (7)0.0494 (7)0.0125 (6)0.0106 (6)0.0143 (6)
O10.0940 (9)0.0589 (7)0.0539 (6)0.0240 (6)0.0296 (6)0.0240 (5)
O20.0844 (9)0.0738 (8)0.0474 (6)0.0007 (6)0.0044 (6)0.0246 (6)
Geometric parameters (Å, º) top
C1—N11.334 (2)C13—H13B1.009 (17)
C1—C21.381 (3)C14—C191.380 (2)
C1—H10.965 (19)C14—C151.389 (2)
C2—C31.366 (3)C15—C161.383 (2)
C2—H20.929 (18)C15—H150.991 (16)
C3—C41.381 (2)C16—C171.388 (2)
C3—H30.98 (2)C16—H160.968 (18)
C4—C51.379 (2)C17—C181.390 (2)
C4—H40.98 (2)C17—N31.4094 (19)
C5—N11.3378 (19)C18—C191.390 (2)
C5—C61.506 (2)C18—H180.988 (17)
C6—O11.2244 (17)C19—H190.992 (18)
C6—N21.3505 (19)C20—O21.2213 (17)
C7—C121.3881 (19)C20—N31.3546 (19)
C7—C81.390 (2)C20—C211.507 (2)
C7—N21.4033 (19)C21—N41.3349 (19)
C8—C91.382 (2)C21—C221.381 (2)
C8—H80.966 (17)C22—C231.381 (2)
C9—C101.384 (2)C22—H220.937 (18)
C9—H90.979 (17)C23—C241.367 (3)
C10—C111.390 (2)C23—H230.97 (2)
C10—C131.511 (2)C24—C251.381 (3)
C11—C121.376 (2)C24—H240.95 (2)
C11—H111.001 (17)C25—N41.330 (2)
C12—H120.968 (16)C25—H250.979 (19)
C13—C141.518 (2)N2—H2B0.896 (18)
C13—H13A1.005 (17)N3—H3B0.919 (17)
N1—C1—C2123.67 (17)C19—C14—C13121.62 (14)
N1—C1—H1114.9 (11)C15—C14—C13121.08 (14)
C2—C1—H1121.4 (11)C16—C15—C14121.41 (14)
C3—C2—C1118.34 (17)C16—C15—H15117.8 (10)
C3—C2—H2122.1 (11)C14—C15—H15120.7 (10)
C1—C2—H2119.4 (11)C15—C16—C17120.61 (14)
C2—C3—C4119.39 (17)C15—C16—H16119.9 (10)
C2—C3—H3117.8 (12)C17—C16—H16119.4 (10)
C4—C3—H3122.8 (12)C16—C17—C18118.79 (14)
C5—C4—C3118.35 (16)C16—C17—N3117.55 (12)
C5—C4—H4120.1 (12)C18—C17—N3123.66 (13)
C3—C4—H4121.6 (12)C19—C18—C17119.50 (14)
N1—C5—C4123.32 (14)C19—C18—H18121.0 (10)
N1—C5—C6116.71 (13)C17—C18—H18119.5 (10)
C4—C5—C6119.96 (13)C14—C19—C18122.41 (14)
O1—C6—N2125.16 (14)C14—C19—H19119.9 (10)
O1—C6—C5121.59 (13)C18—C19—H19117.7 (10)
N2—C6—C5113.25 (12)O2—C20—N3125.00 (14)
C12—C7—C8119.04 (14)O2—C20—C21121.03 (13)
C12—C7—N2117.26 (13)N3—C20—C21113.96 (12)
C8—C7—N2123.70 (13)N4—C21—C22123.28 (15)
C9—C8—C7119.33 (14)N4—C21—C20116.78 (13)
C9—C8—H8121.5 (10)C22—C21—C20119.94 (14)
C7—C8—H8119.2 (10)C23—C22—C21118.37 (16)
C8—C9—C10122.36 (14)C23—C22—H22122.1 (11)
C8—C9—H9119.6 (10)C21—C22—H22119.5 (11)
C10—C9—H9118.1 (10)C24—C23—C22119.22 (17)
C9—C10—C11117.37 (14)C24—C23—H23118.3 (12)
C9—C10—C13121.20 (13)C22—C23—H23122.5 (12)
C11—C10—C13121.35 (13)C23—C24—C25118.30 (18)
C12—C11—C10121.28 (14)C23—C24—H24122.3 (12)
C12—C11—H11118.3 (10)C25—C24—H24119.4 (12)
C10—C11—H11120.4 (10)N4—C25—C24123.88 (17)
C11—C12—C7120.62 (14)N4—C25—H25116.8 (11)
C11—C12—H12121.2 (9)C24—C25—H25119.4 (11)
C7—C12—H12118.2 (10)C1—N1—C5116.91 (14)
C10—C13—C14112.07 (12)C6—N2—C7129.74 (13)
C10—C13—H13A109.3 (9)C6—N2—H2B112.2 (11)
C14—C13—H13A108.8 (9)C7—N2—H2B118.1 (11)
C10—C13—H13B109.6 (9)C20—N3—C17128.40 (13)
C14—C13—H13B108.6 (9)C20—N3—H3B113.9 (10)
H13A—C13—H13B108.4 (13)C17—N3—H3B117.7 (10)
C19—C14—C15117.25 (14)C25—N4—C21116.94 (14)
N1—C1—C2—C31.3 (3)C16—C17—C18—C191.4 (2)
C1—C2—C3—C40.3 (3)N3—C17—C18—C19178.65 (14)
C2—C3—C4—C50.7 (3)C15—C14—C19—C181.2 (2)
C3—C4—C5—N11.0 (2)C13—C14—C19—C18178.96 (14)
C3—C4—C5—C6178.31 (14)C17—C18—C19—C140.1 (2)
N1—C5—C6—O1179.66 (14)O2—C20—C21—N4169.72 (14)
C4—C5—C6—O11.0 (2)N3—C20—C21—N410.74 (18)
N1—C5—C6—N20.96 (18)O2—C20—C21—C2211.1 (2)
C4—C5—C6—N2178.37 (14)N3—C20—C21—C22168.45 (13)
C12—C7—C8—C90.6 (2)N4—C21—C22—C230.1 (2)
N2—C7—C8—C9179.79 (14)C20—C21—C22—C23179.26 (14)
C7—C8—C9—C100.1 (2)C21—C22—C23—C240.5 (3)
C8—C9—C10—C110.7 (2)C22—C23—C24—C250.7 (3)
C8—C9—C10—C13175.98 (14)C23—C24—C25—N40.3 (3)
C9—C10—C11—C120.8 (2)C2—C1—N1—C51.1 (3)
C13—C10—C11—C12175.91 (14)C4—C5—N1—C10.1 (2)
C10—C11—C12—C70.2 (2)C6—C5—N1—C1179.21 (14)
C8—C7—C12—C110.5 (2)O1—C6—N2—C70.2 (3)
N2—C7—C12—C11179.83 (13)C5—C6—N2—C7179.12 (13)
C9—C10—C13—C1487.52 (17)C12—C7—N2—C6174.91 (14)
C11—C10—C13—C1489.05 (17)C8—C7—N2—C65.4 (2)
C10—C13—C14—C1985.86 (18)O2—C20—N3—C170.8 (2)
C10—C13—C14—C1591.77 (17)C21—C20—N3—C17179.65 (12)
C19—C14—C15—C161.3 (2)C16—C17—N3—C20173.37 (14)
C13—C14—C15—C16179.03 (14)C18—C17—N3—C206.7 (2)
C14—C15—C16—C170.0 (2)C24—C25—N4—C210.3 (3)
C15—C16—C17—C181.4 (2)C22—C21—N4—C250.5 (2)
C15—C16—C17—N3178.69 (14)C20—C21—N4—C25179.69 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N10.90 (2)2.125 (19)2.641 (2)115.8 (14)
N3—H3B···N40.920 (19)2.187 (14)2.669 (2)111.8 (13)
N3—H3B···O1i0.920 (19)2.367 (18)3.162 (2)144.6 (14)
Symmetry code: (i) x, y+1, z.
 

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