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In the title compound, C21H15ClN4O3, mol­ecules are linked into dimers by C—H...O hydrogen bonds and are linked into chains along the a axis by C—H...N inter­molecular hydrogen bonds. The packing is further stabilized by C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005132/sg2122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005132/sg2122Isup2.hkl
Contains datablock I

CCDC reference: 640474

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.046
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(1H-Benzotriazol-1-yl)-1-(4-chlorobenzoyl)ethyl isonicotinate top
Crystal data top
C21H15ClN4O3Z = 2
Mr = 406.82F(000) = 420
Triclinic, P1Dx = 1.435 Mg m3
a = 9.902 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.927 (4) ÅCell parameters from 1697 reflections
c = 10.893 (5) Åθ = 2.5–22.9°
α = 114.158 (6)°µ = 0.24 mm1
β = 96.821 (6)°T = 293 K
γ = 99.745 (6)°Block, colourless
V = 941.5 (7) Å30.37 × 0.20 × 0.08 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3525 independent reflections
Radiation source: fine-focus sealed tube2723 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 25.6°, θmin = 2.1°
ω scansh = 912
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1112
Tmin = 0.945, Tmax = 0.981l = 1310
5092 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.2912P]
where P = (Fo2 + 2Fc2)/3
3430 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.18 e Å3
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.

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 (Å2) top
xyzUiso*/Ueq
Cl10.40872 (7)0.63052 (7)0.76580 (6)0.0611 (2)
O20.22400 (15)0.05077 (16)0.02597 (13)0.0419 (4)
O30.41580 (17)0.10552 (18)0.02740 (15)0.0543 (4)
O10.14133 (17)0.19898 (18)0.09759 (15)0.0546 (4)
N20.3368 (2)0.2187 (2)0.22366 (19)0.0518 (5)
N10.22573 (18)0.22637 (19)0.13306 (16)0.0383 (4)
C70.2162 (2)0.1712 (2)0.1762 (2)0.0380 (5)
C60.2660 (2)0.2800 (2)0.3243 (2)0.0366 (5)
C100.1906 (2)0.3635 (2)0.0211 (2)0.0378 (5)
C160.3078 (2)0.0117 (2)0.0868 (2)0.0374 (5)
C80.2571 (2)0.0184 (2)0.12185 (19)0.0374 (5)
H8A0.35720.03310.15570.045*
C50.3483 (2)0.2524 (2)0.4197 (2)0.0427 (5)
H5A0.37540.16090.39120.051*
C90.1697 (2)0.0936 (2)0.1619 (2)0.0394 (5)
H9A0.16930.04400.25920.047*
H9B0.07380.12460.11100.047*
C170.2480 (2)0.0463 (2)0.2366 (2)0.0380 (5)
C40.3909 (2)0.3581 (3)0.5564 (2)0.0469 (6)
H4A0.44500.33770.61960.056*
C30.3517 (2)0.4937 (3)0.5971 (2)0.0450 (5)
C210.3306 (3)0.0094 (3)0.3167 (2)0.0519 (6)
H21A0.42290.04690.27940.062*
N30.3742 (2)0.3468 (3)0.1737 (2)0.0592 (6)
N40.1408 (2)0.1340 (3)0.5136 (2)0.0691 (6)
C150.0856 (2)0.4284 (3)0.0974 (2)0.0490 (6)
H15A0.02220.37560.11430.059*
C10.2290 (3)0.4185 (3)0.3686 (2)0.0515 (6)
H1A0.17510.43970.30590.062*
C20.2709 (3)0.5247 (3)0.5038 (2)0.0564 (6)
H2B0.24510.61690.53240.068*
C180.1121 (2)0.1286 (3)0.2970 (2)0.0537 (6)
H18A0.05410.15780.24660.064*
C110.2865 (2)0.4404 (3)0.0481 (2)0.0475 (6)
C200.2731 (3)0.0581 (3)0.4542 (3)0.0647 (7)
H20A0.33060.03640.50860.078*
C190.0638 (3)0.1670 (3)0.4336 (3)0.0700 (8)
H19A0.02930.21960.47240.084*
C140.0811 (3)0.5741 (3)0.1876 (3)0.0618 (7)
H14A0.01170.62270.26750.074*
C120.2811 (3)0.5887 (3)0.0465 (3)0.0654 (7)
H12A0.34480.64170.03080.078*
C130.1783 (3)0.6527 (3)0.1630 (3)0.0696 (8)
H13A0.17250.75110.22800.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0689 (4)0.0544 (4)0.0338 (3)0.0014 (3)0.0071 (3)0.0012 (3)
O20.0487 (9)0.0415 (8)0.0261 (7)0.0022 (6)0.0061 (6)0.0097 (6)
O30.0551 (10)0.0549 (10)0.0383 (9)0.0071 (8)0.0009 (7)0.0171 (8)
O10.0651 (11)0.0579 (10)0.0357 (9)0.0228 (8)0.0023 (8)0.0160 (8)
N20.0514 (12)0.0609 (13)0.0394 (11)0.0077 (10)0.0034 (9)0.0243 (10)
N10.0434 (10)0.0392 (10)0.0297 (9)0.0067 (8)0.0024 (7)0.0151 (8)
C70.0396 (11)0.0404 (11)0.0309 (11)0.0072 (9)0.0042 (9)0.0144 (9)
C60.0382 (11)0.0358 (11)0.0309 (11)0.0062 (9)0.0057 (9)0.0113 (9)
C100.0420 (12)0.0356 (11)0.0356 (11)0.0067 (9)0.0085 (9)0.0164 (9)
C160.0441 (12)0.0333 (11)0.0323 (11)0.0113 (9)0.0080 (9)0.0112 (9)
C80.0424 (11)0.0373 (11)0.0250 (10)0.0069 (9)0.0031 (8)0.0084 (9)
C50.0512 (13)0.0395 (12)0.0346 (12)0.0120 (10)0.0052 (10)0.0144 (10)
C90.0440 (12)0.0390 (12)0.0306 (11)0.0089 (9)0.0087 (9)0.0112 (9)
C170.0451 (12)0.0338 (11)0.0297 (11)0.0103 (9)0.0062 (9)0.0090 (9)
C40.0526 (14)0.0492 (13)0.0342 (12)0.0068 (11)0.0009 (10)0.0182 (10)
C30.0445 (12)0.0431 (12)0.0316 (11)0.0019 (10)0.0069 (9)0.0063 (9)
C210.0549 (14)0.0529 (14)0.0387 (13)0.0024 (11)0.0055 (11)0.0182 (11)
N30.0584 (13)0.0684 (14)0.0601 (14)0.0204 (11)0.0032 (11)0.0376 (12)
N40.0685 (15)0.0910 (17)0.0358 (11)0.0081 (13)0.0006 (11)0.0231 (12)
C150.0507 (13)0.0478 (13)0.0384 (13)0.0082 (10)0.0021 (10)0.0127 (11)
C10.0580 (15)0.0442 (13)0.0438 (13)0.0160 (11)0.0039 (11)0.0137 (11)
C20.0640 (16)0.0414 (13)0.0489 (14)0.0177 (11)0.0016 (12)0.0062 (11)
C180.0452 (13)0.0704 (16)0.0359 (13)0.0064 (12)0.0087 (10)0.0167 (12)
C110.0520 (14)0.0468 (13)0.0511 (14)0.0136 (11)0.0120 (11)0.0277 (11)
C200.0766 (19)0.0728 (18)0.0408 (14)0.0024 (14)0.0125 (13)0.0270 (13)
C190.0480 (15)0.099 (2)0.0407 (14)0.0046 (14)0.0010 (12)0.0162 (14)
C140.0688 (17)0.0495 (15)0.0457 (14)0.0001 (13)0.0074 (12)0.0069 (12)
C120.0802 (19)0.0513 (16)0.082 (2)0.0294 (14)0.0285 (17)0.0371 (15)
C130.096 (2)0.0365 (13)0.0694 (19)0.0151 (14)0.0314 (17)0.0127 (13)
Geometric parameters (Å, º) top
Cl1—C31.729 (2)C4—C31.373 (3)
O2—C161.344 (2)C4—H4A0.9300
O2—C81.437 (2)C3—C21.384 (3)
O3—C161.198 (2)C21—C201.383 (3)
O1—C71.212 (2)C21—H21A0.9300
N2—N31.301 (3)N3—C111.376 (3)
N2—N11.357 (2)N4—C191.324 (3)
N1—C101.357 (3)N4—C201.330 (3)
N1—C91.447 (3)C15—C141.365 (3)
C7—C61.488 (3)C15—H15A0.9300
C7—C81.532 (3)C1—C21.374 (3)
C6—C51.388 (3)C1—H1A0.9300
C6—C11.389 (3)C2—H2B0.9300
C10—C111.391 (3)C18—C191.376 (3)
C10—C151.392 (3)C18—H18A0.9300
C16—C171.493 (3)C11—C121.396 (3)
C8—C91.529 (3)C20—H20A0.9300
C8—H8A0.9800C19—H19A0.9300
C5—C41.386 (3)C14—C131.403 (4)
C5—H5A0.9300C14—H14A0.9300
C9—H9A0.9700C12—C131.366 (4)
C9—H9B0.9700C12—H12A0.9300
C17—C181.374 (3)C13—H13A0.9300
C17—C211.378 (3)
C16—O2—C8116.29 (15)C4—C3—C2120.9 (2)
N3—N2—N1108.64 (18)C4—C3—Cl1119.80 (18)
N2—N1—C10110.49 (18)C2—C3—Cl1119.29 (19)
N2—N1—C9119.12 (17)C17—C21—C20118.3 (2)
C10—N1—C9130.27 (17)C17—C21—H21A120.8
O1—C7—C6121.7 (2)C20—C21—H21A120.8
O1—C7—C8118.86 (18)N2—N3—C11108.24 (18)
C6—C7—C8119.41 (17)C19—N4—C20116.0 (2)
C5—C6—C1118.27 (19)C14—C15—C10116.1 (2)
C5—C6—C7124.23 (19)C14—C15—H15A121.9
C1—C6—C7117.50 (18)C10—C15—H15A121.9
N1—C10—C11104.01 (18)C2—C1—C6120.9 (2)
N1—C10—C15133.2 (2)C2—C1—H1A119.6
C11—C10—C15122.8 (2)C6—C1—H1A119.6
O3—C16—O2124.08 (19)C1—C2—C3119.7 (2)
O3—C16—C17124.03 (19)C1—C2—H2B120.2
O2—C16—C17111.86 (17)C3—C2—H2B120.2
O2—C8—C9105.20 (15)C17—C18—C19118.6 (2)
O2—C8—C7108.92 (16)C17—C18—H18A120.7
C9—C8—C7111.32 (17)C19—C18—H18A120.7
O2—C8—H8A110.4N3—C11—C10108.6 (2)
C9—C8—H8A110.4N3—C11—C12131.3 (2)
C7—C8—H8A110.4C10—C11—C12120.1 (2)
C4—C5—C6121.5 (2)N4—C20—C21124.2 (2)
C4—C5—H5A119.3N4—C20—H20A117.9
C6—C5—H5A119.3C21—C20—H20A117.9
N1—C9—C8110.97 (17)N4—C19—C18124.5 (2)
N1—C9—H9A109.4N4—C19—H19A117.8
C8—C9—H9A109.4C18—C19—H19A117.8
N1—C9—H9B109.4C15—C14—C13121.8 (2)
C8—C9—H9B109.4C15—C14—H14A119.1
H9A—C9—H9B108.0C13—C14—H14A119.1
C18—C17—C21118.3 (2)C13—C12—C11117.2 (2)
C18—C17—C16123.1 (2)C13—C12—H12A121.4
C21—C17—C16118.49 (19)C11—C12—H12A121.4
C3—C4—C5118.8 (2)C12—C13—C14121.9 (2)
C3—C4—H4A120.6C12—C13—H13A119.0
C5—C4—H4A120.6C14—C13—H13A119.0
N3—N2—N1—C100.2 (2)C5—C4—C3—C20.2 (3)
N3—N2—N1—C9176.46 (18)C5—C4—C3—Cl1177.66 (17)
O1—C7—C6—C5178.0 (2)C18—C17—C21—C200.6 (4)
C8—C7—C6—C50.5 (3)C16—C17—C21—C20177.4 (2)
O1—C7—C6—C12.9 (3)N1—N2—N3—C110.1 (2)
C8—C7—C6—C1178.64 (19)N1—C10—C15—C14178.3 (2)
N2—N1—C10—C110.2 (2)C11—C10—C15—C140.1 (3)
C9—N1—C10—C11175.92 (19)C5—C6—C1—C20.9 (3)
N2—N1—C10—C15178.7 (2)C7—C6—C1—C2179.9 (2)
C9—N1—C10—C155.5 (4)C6—C1—C2—C30.3 (4)
C8—O2—C16—O310.2 (3)C4—C3—C2—C10.1 (4)
C8—O2—C16—C17168.07 (16)Cl1—C3—C2—C1177.91 (19)
C16—O2—C8—C9167.48 (16)C21—C17—C18—C191.6 (4)
C16—O2—C8—C773.1 (2)C16—C17—C18—C19175.1 (2)
O1—C7—C8—O214.1 (3)N2—N3—C11—C100.0 (3)
C6—C7—C8—O2167.43 (17)N2—N3—C11—C12179.6 (2)
O1—C7—C8—C9101.5 (2)N1—C10—C11—N30.1 (2)
C6—C7—C8—C977.0 (2)C15—C10—C11—N3178.9 (2)
C1—C6—C5—C41.2 (3)N1—C10—C11—C12179.5 (2)
C7—C6—C5—C4179.7 (2)C15—C10—C11—C120.8 (3)
N2—N1—C9—C880.9 (2)C19—N4—C20—C212.2 (4)
C10—N1—C9—C894.6 (2)C17—C21—C20—N42.6 (4)
O2—C8—C9—N172.8 (2)C20—N4—C19—C180.3 (5)
C7—C8—C9—N1169.34 (16)C17—C18—C19—N42.2 (5)
O3—C16—C17—C18165.9 (2)C10—C15—C14—C131.1 (4)
O2—C16—C17—C1812.3 (3)N3—C11—C12—C13178.9 (2)
O3—C16—C17—C2110.8 (3)C10—C11—C12—C130.7 (4)
O2—C16—C17—C21170.95 (19)C11—C12—C13—C140.3 (4)
C6—C5—C4—C30.8 (3)C15—C14—C13—C121.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···Cg2i0.932.813.739174
C15—H15A···O1ii0.932.553.460 (3)166
C21—H21A···N2iii0.932.523.436 (4)166
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z; (iii) x+1, y, z.
 

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