PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o995.
Published online 2009 April 8. doi:  10.1107/S1600536809012409
PMCID: PMC2977687

4-(4-Chloro­phen­yl)-6-meth­oxy-2,2′-bipyridine-5-carbonitrile

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C18H12ClN3O. The two pyridine rings are almost coplanar [dihedral angles between the rings: 2.87 (15) and 5.36 (16)°] while the chloro­phenyl rings are twisted out of the plane of the adjacent bipyridine ring by 44.1 (1) and 43.8 (1)° in the two mol­ecules. The crystal packing is stabilized by C—H(...)N and C—H(...)Cl inter­actions.

Related literature

Pyridine derivatives possess phospho­diesterase-inhibiting (Heintzelman et al., 2003a [triangle],b [triangle]), anti­fungal (Cook et al., 2004a [triangle],b [triangle]), anti­fertility (Upton et al., 2000 [triangle]) and anti­arrhythmic activities (Ellefson et al., 1978 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o995-scheme1.jpg

Experimental

Crystal data

  • C18H12ClN3O
  • M r = 321.76
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o995-efi1.jpg
  • a = 9.5869 (5) Å
  • b = 13.8761 (7) Å
  • c = 12.2124 (6) Å
  • β = 106.896 (2)°
  • V = 1554.47 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.927, T max = 0.951
  • 17581 measured reflections
  • 6950 independent reflections
  • 4300 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.113
  • S = 1.00
  • 6950 reflections
  • 417 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.18 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3268 Friedel pairs
  • Flack parameter: 0.05 (6)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012409/bt2899sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012409/bt2899Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Pyridine derivatives possess phosphodiesterase inhibiting (Heintzelman et al., 2003a,b), antifungal (Cook et al., 2004a,b), antifertility (Upton et al.,2000) and antiarrhythmic activities (Ellefson et al., 1978). The crystallographic study was useful to ascertain the molecular conformation.

The ORTEP plot of the molecule is shown in Fig.1. There are two crystallographically independent molecules in the asymmetric unit. The two pyridine rings lie in the same plane which is evidenced from the dihedral angles of 2.87 (15)° and 5.36 (16)° for the molecules 1 & 2 respectively. The planar chlorophenyl rings are twisted away from the bipyridine ring by 44.1 (1)° for (molecule 1) and 43.8 (1)° for (molecule 2), respectively. The bond angles of C3—C8—N9 (177.9 (4))° and C3'-C8'-N9' (178.3 (3))° show linearity of the cyano group, a feature observed in carbonitrile compounds.

The crystal packing is controlled by C—H···N and C—H···Cl intermolecular interactions in addition to van der Waals forces. Atoms C11 and C11' at (x, y, z) donate one proton each to N9' (-x,+y + 1/2,-z + 2) and N9 (-x,+y - 1/2,-z + 2) which connect the molecules to form a dimer with a graph-set-motiff R22(14) (Bernstein et al., 1995). These dimers are linked through intermolecular C21—H21···Cl1 hydrogen bond chain running along c axis which is shown in Fig. 2.

Experimental

A mixture of p-chlorobenzaldehyde (1 eq), 2-acetyl pyridine and sodium hydroxide (1.2 eq) in methanol was refluxed for 30 min. After that malanonitrile (1 eq) was added and the reaction was continued to 3 h. With the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 76% yield (90:10, petroleum ether: ethyl acetate). The compound was recrystallized in ethanol.

Refinement

All H atoms were positioned geometrically (C—H=0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H, 1.2Ueq(C) for other H atoms.

Figures

Fig. 1.
Perspective view of the molecule showing the displacement ellipsoids at 50% probability level. The H atoms are shown as small circles of arbitrary radii.
Fig. 2.
The crystal packing of the molecules viewed down b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C18H12ClN3OF(000) = 664
Mr = 321.76Dx = 1.375 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3721 reflections
a = 9.5869 (5) Åθ = 1.7–27.5°
b = 13.8761 (7) ŵ = 0.25 mm1
c = 12.2124 (6) ÅT = 293 K
β = 106.896 (2)°Block, colorless
V = 1554.47 (14) Å30.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII area-detector diffractometer6950 independent reflections
Radiation source: fine-focus sealed tube4300 reflections with I > 2σ(I)
graphiteRint = 0.035
ω and [var phi] scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −12→12
Tmin = 0.927, Tmax = 0.951k = −17→17
17581 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.113w = 1/[σ2(Fo2) + (0.0461P)2 + 0.1394P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
6950 reflectionsΔρmax = 0.24 e Å3
417 parametersΔρmin = −0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 3268 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (6)

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 (Å2)

xyzUiso*/Ueq
C2'−0.0524 (3)0.2747 (2)0.5616 (2)0.0453 (7)
C2−0.1641 (3)0.5282 (2)0.7627 (2)0.0485 (7)
C3'0.0529 (3)0.2755 (2)0.66886 (19)0.0438 (6)
C3−0.0610 (3)0.5309 (2)0.86978 (19)0.0448 (6)
C4'0.1994 (3)0.2704 (2)0.67256 (19)0.0450 (6)
C40.0852 (3)0.53628 (19)0.87589 (19)0.0427 (6)
C50.1208 (3)0.5349 (2)0.77260 (19)0.0452 (6)
H50.21770.53730.77260.054*
C5'0.2306 (3)0.2696 (2)0.56900 (19)0.0467 (6)
H5'0.32710.26720.56790.056*
C60.0109 (3)0.5301 (2)0.6710 (2)0.0439 (6)
C6'0.1199 (3)0.2723 (2)0.4671 (2)0.0430 (6)
C7'−0.3014 (3)0.2777 (3)0.4542 (2)0.0730 (9)
H7D−0.28430.33070.40920.110*
H7F−0.39570.28450.46580.110*
H7E−0.29770.21830.41470.110*
C7−0.4109 (3)0.5274 (3)0.6510 (2)0.0769 (10)
H7A−0.38620.57660.60460.115*
H7B−0.50540.54070.65980.115*
H7C−0.41250.46590.61470.115*
C8'0.0057 (3)0.2856 (2)0.7694 (2)0.0506 (7)
C8−0.1112 (3)0.5223 (2)0.9698 (2)0.0509 (7)
C100.2010 (3)0.5420 (2)0.9863 (2)0.0452 (7)
C10'0.3164 (3)0.2671 (2)0.78201 (19)0.0451 (6)
C110.1893 (3)0.6056 (2)1.0710 (2)0.0488 (7)
H110.10810.64551.05750.059*
C11'0.3071 (3)0.2046 (2)0.8686 (2)0.0540 (7)
H11'0.22620.16460.85730.065*
C12'0.4158 (3)0.2011 (2)0.9709 (2)0.0601 (8)
H12'0.40890.15871.02810.072*
C120.2950 (3)0.6106 (2)1.1738 (2)0.0540 (7)
H120.28670.65381.22980.065*
C13'0.5332 (3)0.2601 (3)0.9877 (2)0.0609 (9)
C130.4138 (3)0.5507 (3)1.1932 (2)0.0565 (8)
C140.4309 (3)0.4900 (3)1.1102 (2)0.0646 (9)
H140.51410.45201.12330.078*
C14'0.5486 (3)0.3210 (3)0.9047 (3)0.0661 (9)
H14'0.63070.36000.91720.079*
C15'0.4401 (3)0.3240 (2)0.8012 (2)0.0567 (8)
H15'0.45040.36480.74360.068*
C150.3241 (3)0.4854 (2)1.0067 (2)0.0572 (8)
H150.33510.44380.95010.069*
C160.0424 (3)0.5259 (2)0.5593 (2)0.0454 (7)
C16'0.1494 (3)0.2756 (2)0.3547 (2)0.0464 (6)
C18'0.3136 (4)0.2815 (3)0.2542 (3)0.0821 (11)
H18'0.40990.28070.25240.098*
C180.2082 (4)0.5207 (3)0.4595 (3)0.0717 (10)
H180.30520.52020.45940.086*
C190.1032 (4)0.5161 (2)0.3559 (3)0.0662 (10)
H190.12840.51280.28800.079*
C19'0.2062 (4)0.2900 (3)0.1528 (2)0.0715 (10)
H19'0.22990.29500.08440.086*
C20'0.0658 (4)0.2910 (3)0.1527 (2)0.0643 (9)
H20'−0.00910.29680.08480.077*
C20−0.0384 (4)0.5166 (3)0.3552 (2)0.0629 (9)
H20−0.11270.51330.28660.075*
C21−0.0705 (3)0.5222 (2)0.4585 (2)0.0554 (7)
H21−0.16680.52360.46010.067*
C21'0.0364 (3)0.2832 (2)0.2554 (2)0.0550 (8)
H21'−0.05960.28310.25810.066*
N1−0.1311 (2)0.52769 (17)0.66537 (16)0.0476 (6)
N1'−0.0218 (2)0.27322 (17)0.46358 (16)0.0477 (5)
N9'−0.0333 (3)0.2959 (2)0.8486 (2)0.0696 (8)
N9−0.1527 (3)0.5130 (2)1.0466 (2)0.0711 (8)
N17'0.2879 (3)0.2742 (2)0.35573 (18)0.0655 (7)
N170.1810 (3)0.5257 (2)0.56052 (18)0.0594 (7)
O1−0.3049 (2)0.52612 (18)0.76094 (15)0.0623 (6)
O1'−0.1919 (2)0.27689 (18)0.56248 (16)0.0617 (6)
Cl1'0.66572 (10)0.25841 (9)1.11925 (7)0.0970 (4)
Cl10.54493 (9)0.55353 (8)1.32596 (6)0.0888 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C2'0.0455 (16)0.0402 (16)0.0507 (15)−0.0023 (15)0.0149 (12)0.0032 (13)
C20.0441 (15)0.0460 (17)0.0545 (15)−0.0014 (14)0.0130 (12)0.0042 (14)
C3'0.0524 (16)0.0416 (16)0.0372 (13)−0.0055 (15)0.0126 (11)0.0029 (14)
C30.0522 (16)0.0423 (15)0.0408 (13)0.0036 (14)0.0149 (11)0.0003 (13)
C4'0.0522 (15)0.0395 (15)0.0422 (13)−0.0043 (15)0.0121 (11)0.0023 (14)
C40.0472 (15)0.0382 (15)0.0422 (13)0.0042 (13)0.0120 (11)−0.0021 (13)
C50.0436 (14)0.0473 (16)0.0448 (13)0.0024 (13)0.0130 (10)−0.0011 (13)
C5'0.0505 (15)0.0454 (16)0.0433 (13)0.0005 (14)0.0122 (11)0.0043 (13)
C60.0504 (16)0.0392 (15)0.0416 (13)−0.0009 (13)0.0128 (11)−0.0008 (13)
C6'0.0496 (16)0.0355 (14)0.0427 (13)0.0009 (14)0.0113 (11)0.0023 (13)
C7'0.0506 (17)0.090 (3)0.0700 (19)0.002 (2)0.0034 (14)0.000 (2)
C70.0470 (17)0.102 (3)0.074 (2)−0.010 (2)0.0058 (14)0.011 (2)
C8'0.0565 (18)0.0444 (19)0.0512 (16)−0.0023 (16)0.0161 (14)0.0052 (14)
C80.0524 (16)0.0514 (18)0.0482 (15)0.0058 (15)0.0137 (12)−0.0002 (15)
C100.0432 (15)0.0486 (17)0.0427 (13)−0.0014 (14)0.0108 (11)0.0027 (14)
C10'0.0512 (15)0.0468 (15)0.0377 (12)−0.0019 (14)0.0135 (10)−0.0030 (13)
C110.0535 (17)0.0529 (17)0.0414 (14)0.0028 (14)0.0159 (12)−0.0007 (13)
C11'0.0587 (18)0.0557 (18)0.0451 (15)−0.0016 (14)0.0110 (12)0.0012 (14)
C12'0.068 (2)0.066 (2)0.0444 (15)0.0144 (17)0.0133 (14)0.0025 (15)
C120.0605 (18)0.0609 (19)0.0416 (14)−0.0107 (16)0.0167 (13)−0.0050 (13)
C13'0.0528 (18)0.076 (2)0.0464 (15)0.0167 (18)0.0034 (13)−0.0115 (17)
C130.0516 (17)0.069 (2)0.0411 (14)−0.0138 (17)0.0015 (12)0.0058 (16)
C140.0552 (19)0.068 (2)0.0638 (19)0.0076 (17)0.0063 (16)0.0046 (18)
C14'0.0426 (17)0.078 (2)0.074 (2)−0.0076 (16)0.0120 (16)−0.0202 (19)
C15'0.0550 (18)0.060 (2)0.0569 (17)−0.0061 (15)0.0200 (14)−0.0035 (15)
C150.0569 (18)0.057 (2)0.0541 (16)0.0098 (15)0.0107 (14)−0.0035 (15)
C160.0549 (17)0.0386 (16)0.0418 (14)−0.0049 (15)0.0124 (12)−0.0012 (13)
C16'0.0569 (16)0.0394 (15)0.0427 (13)−0.0013 (15)0.0143 (11)−0.0003 (13)
C18'0.076 (2)0.122 (3)0.0567 (18)0.010 (2)0.0321 (16)0.009 (2)
C180.077 (2)0.083 (3)0.065 (2)−0.008 (2)0.0367 (18)−0.004 (2)
C190.097 (3)0.059 (2)0.0525 (18)−0.012 (2)0.0378 (18)−0.0001 (16)
C19'0.094 (3)0.081 (3)0.0451 (16)0.003 (2)0.0294 (17)0.0030 (18)
C20'0.083 (2)0.065 (2)0.0393 (15)−0.0019 (19)0.0100 (15)−0.0059 (16)
C200.085 (2)0.058 (2)0.0422 (16)−0.0044 (19)0.0135 (16)0.0041 (15)
C210.0601 (18)0.0571 (19)0.0465 (15)0.0019 (16)0.0113 (12)0.0031 (14)
C21'0.0580 (17)0.062 (2)0.0438 (15)−0.0013 (16)0.0121 (12)−0.0027 (15)
N10.0496 (13)0.0515 (15)0.0400 (11)−0.0026 (12)0.0102 (9)0.0012 (11)
N1'0.0509 (13)0.0470 (13)0.0436 (12)−0.0002 (13)0.0113 (10)0.0018 (11)
N9'0.093 (2)0.0659 (19)0.0600 (16)−0.0049 (15)0.0382 (15)0.0010 (14)
N90.0778 (18)0.084 (2)0.0598 (15)0.0023 (16)0.0336 (13)−0.0006 (15)
N17'0.0601 (16)0.089 (2)0.0499 (13)0.0088 (17)0.0201 (11)0.0099 (15)
N170.0592 (15)0.0710 (18)0.0500 (13)−0.0052 (15)0.0190 (11)−0.0064 (14)
O10.0460 (11)0.0844 (17)0.0555 (11)−0.0024 (12)0.0132 (9)0.0104 (12)
O1'0.0462 (11)0.0785 (16)0.0605 (12)0.0000 (12)0.0160 (9)−0.0005 (12)
Cl1'0.0709 (5)0.1312 (9)0.0664 (5)0.0322 (6)−0.0157 (4)−0.0216 (6)
Cl10.0726 (5)0.1207 (8)0.0551 (4)−0.0156 (5)−0.0101 (3)0.0127 (5)

Geometric parameters (Å, °)

C2'—N1'1.313 (3)C11—H110.9300
C2'—O1'1.341 (3)C11'—C12'1.375 (3)
C2'—C3'1.403 (3)C11'—H11'0.9300
C2—N11.316 (3)C12'—C13'1.358 (5)
C2—O11.344 (3)C12'—H12'0.9300
C2—C31.391 (3)C12—C131.374 (4)
C3'—C4'1.394 (3)C12—H120.9300
C3'—C8'1.433 (4)C13'—C14'1.361 (5)
C3—C41.384 (3)C13'—Cl1'1.735 (3)
C3—C81.442 (4)C13—C141.364 (4)
C4'—C5'1.382 (3)C13—Cl11.739 (3)
C4'—C10'1.475 (3)C14—C151.378 (4)
C4—C51.399 (3)C14—H140.9300
C4—C101.478 (3)C14'—C15'1.384 (4)
C5—C61.376 (3)C14'—H14'0.9300
C5—H50.9300C15'—H15'0.9300
C5'—C6'1.382 (3)C15—H150.9300
C5'—H5'0.9300C16—N171.324 (3)
C6—N11.343 (3)C16—C211.384 (3)
C6—C161.481 (3)C16'—N17'1.325 (3)
C6'—N1'1.346 (3)C16'—C21'1.376 (3)
C6'—C16'1.481 (3)C18'—N17'1.337 (4)
C7'—O1'1.430 (3)C18'—C19'1.366 (4)
C7'—H7D0.9600C18'—H18'0.9300
C7'—H7F0.9600C18—N171.335 (3)
C7'—H7E0.9600C18—C191.370 (4)
C7—O11.430 (3)C18—H180.9300
C7—H7A0.9600C19—C201.355 (4)
C7—H7B0.9600C19—H190.9300
C7—H7C0.9600C19'—C20'1.346 (4)
C8'—N9'1.143 (4)C19'—H19'0.9300
C8—N91.127 (3)C20'—C21'1.367 (4)
C10—C151.379 (4)C20'—H20'0.9300
C10—C111.388 (4)C20—C211.384 (4)
C10'—C15'1.387 (4)C20—H200.9300
C10'—C11'1.391 (4)C21—H210.9300
C11—C121.368 (4)C21'—H21'0.9300
N1'—C2'—O1'119.7 (2)C11'—C12'—H12'120.3
N1'—C2'—C3'124.1 (2)C11—C12—C13118.9 (3)
O1'—C2'—C3'116.2 (2)C11—C12—H12120.5
N1—C2—O1119.3 (2)C13—C12—H12120.5
N1—C2—C3123.9 (2)C12'—C13'—C14'121.7 (3)
O1—C2—C3116.8 (2)C12'—C13'—Cl1'118.9 (3)
C4'—C3'—C2'118.4 (2)C14'—C13'—Cl1'119.3 (3)
C4'—C3'—C8'122.9 (2)C14—C13—C12121.2 (2)
C2'—C3'—C8'118.7 (2)C14—C13—Cl1119.8 (3)
C4—C3—C2118.9 (2)C12—C13—Cl1119.0 (2)
C4—C3—C8122.8 (2)C13—C14—C15119.5 (3)
C2—C3—C8118.2 (2)C13—C14—H14120.2
C5'—C4'—C3'117.0 (2)C15—C14—H14120.2
C5'—C4'—C10'121.3 (2)C13'—C14'—C15'118.9 (3)
C3'—C4'—C10'121.6 (2)C13'—C14'—H14'120.5
C3—C4—C5117.3 (2)C15'—C14'—H14'120.5
C3—C4—C10122.1 (2)C14'—C15'—C10'121.0 (3)
C5—C4—C10120.5 (2)C14'—C15'—H15'119.5
C6—C5—C4119.4 (2)C10'—C15'—H15'119.5
C6—C5—H5120.3C14—C15—C10120.6 (3)
C4—C5—H5120.3C14—C15—H15119.7
C4'—C5'—C6'120.7 (2)C10—C15—H15119.7
C4'—C5'—H5'119.7N17—C16—C21122.2 (2)
C6'—C5'—H5'119.7N17—C16—C6117.5 (2)
N1—C6—C5123.1 (2)C21—C16—C6120.3 (2)
N1—C6—C16115.3 (2)N17'—C16'—C21'122.7 (2)
C5—C6—C16121.6 (2)N17'—C16'—C6'116.9 (2)
N1'—C6'—C5'122.2 (2)C21'—C16'—C6'120.4 (3)
N1'—C6'—C16'115.6 (2)N17'—C18'—C19'123.6 (3)
C5'—C6'—C16'122.1 (2)N17'—C18'—H18'118.2
O1'—C7'—H7D109.5C19'—C18'—H18'118.2
O1'—C7'—H7F109.5N17—C18—C19124.5 (3)
H7D—C7'—H7F109.5N17—C18—H18117.7
O1'—C7'—H7E109.5C19—C18—H18117.7
H7D—C7'—H7E109.5C20—C19—C18118.1 (3)
H7F—C7'—H7E109.5C20—C19—H19120.9
O1—C7—H7A109.5C18—C19—H19120.9
O1—C7—H7B109.5C20'—C19'—C18'119.5 (3)
H7A—C7—H7B109.5C20'—C19'—H19'120.3
O1—C7—H7C109.5C18'—C19'—H19'120.3
H7A—C7—H7C109.5C19'—C20'—C21'118.1 (3)
H7B—C7—H7C109.5C19'—C20'—H20'120.9
N9'—C8'—C3'178.3 (4)C21'—C20'—H20'120.9
N9—C8—C3177.9 (3)C19—C20—C21118.8 (3)
C15—C10—C11118.5 (2)C19—C20—H20120.6
C15—C10—C4120.7 (2)C21—C20—H20120.6
C11—C10—C4120.8 (2)C16—C21—C20119.3 (3)
C15'—C10'—C11'117.9 (2)C16—C21—H21120.4
C15'—C10'—C4'121.6 (2)C20—C21—H21120.4
C11'—C10'—C4'120.6 (2)C20'—C21'—C16'119.7 (3)
C12—C11—C10121.2 (3)C20'—C21'—H21'120.2
C12—C11—H11119.4C16'—C21'—H21'120.2
C10—C11—H11119.4C2—N1—C6117.4 (2)
C12'—C11'—C10'120.9 (3)C2'—N1'—C6'117.50 (19)
C12'—C11'—H11'119.6C16'—N17'—C18'116.4 (3)
C10'—C11'—H11'119.6C16—N17—C18117.1 (2)
C13'—C12'—C11'119.5 (3)C2—O1—C7116.9 (2)
C13'—C12'—H12'120.3C2'—O1'—C7'117.3 (2)
N1'—C2'—C3'—C4'−2.8 (5)C12—C13—C14—C15−3.0 (5)
O1'—C2'—C3'—C4'178.1 (3)Cl1—C13—C14—C15177.6 (2)
N1'—C2'—C3'—C8'174.6 (3)C12'—C13'—C14'—C15'1.2 (5)
O1'—C2'—C3'—C8'−4.5 (4)Cl1'—C13'—C14'—C15'−178.0 (2)
N1—C2—C3—C42.0 (4)C13'—C14'—C15'—C10'0.8 (5)
O1—C2—C3—C4−178.0 (3)C11'—C10'—C15'—C14'−2.1 (4)
N1—C2—C3—C8−174.4 (3)C4'—C10'—C15'—C14'179.4 (3)
O1—C2—C3—C85.6 (4)C13—C14—C15—C100.5 (5)
C2'—C3'—C4'—C5'3.1 (4)C11—C10—C15—C141.8 (4)
C8'—C3'—C4'—C5'−174.2 (3)C4—C10—C15—C14−179.2 (3)
C2'—C3'—C4'—C10'−177.7 (3)N1—C6—C16—N17−178.4 (3)
C8'—C3'—C4'—C10'5.1 (5)C5—C6—C16—N170.8 (4)
C2—C3—C4—C5−2.4 (4)N1—C6—C16—C211.6 (4)
C8—C3—C4—C5173.8 (3)C5—C6—C16—C21−179.2 (3)
C2—C3—C4—C10178.3 (3)N1'—C6'—C16'—N17'−179.6 (3)
C8—C3—C4—C10−5.4 (4)C5'—C6'—C16'—N17'1.2 (4)
C3—C4—C5—C61.1 (4)N1'—C6'—C16'—C21'2.5 (4)
C10—C4—C5—C6−179.6 (3)C5'—C6'—C16'—C21'−176.7 (3)
C3'—C4'—C5'—C6'−1.0 (4)N17—C18—C19—C20−0.1 (6)
C10'—C4'—C5'—C6'179.7 (3)N17'—C18'—C19'—C20'−0.2 (7)
C4—C5—C6—N10.8 (4)C18'—C19'—C20'—C21'−0.1 (6)
C4—C5—C6—C16−178.3 (3)C18—C19—C20—C210.3 (5)
C4'—C5'—C6'—N1'−1.8 (4)N17—C16—C21—C201.1 (5)
C4'—C5'—C6'—C16'177.4 (3)C6—C16—C21—C20−178.9 (3)
C4'—C3'—C8'—N9'116 (12)C19—C20—C21—C16−0.8 (5)
C2'—C3'—C8'—N9'−62 (12)C19'—C20'—C21'—C16'0.6 (5)
C4—C3—C8—N9−124 (9)N17'—C16'—C21'—C20'−0.9 (5)
C2—C3—C8—N952 (9)C6'—C16'—C21'—C20'176.8 (3)
C3—C4—C10—C15134.3 (3)O1—C2—N1—C6179.8 (3)
C5—C4—C10—C15−45.0 (4)C3—C2—N1—C6−0.2 (4)
C3—C4—C10—C11−46.8 (4)C5—C6—N1—C2−1.2 (4)
C5—C4—C10—C11134.0 (3)C16—C6—N1—C2177.9 (2)
C5'—C4'—C10'—C15'45.0 (4)O1'—C2'—N1'—C6'179.2 (3)
C3'—C4'—C10'—C15'−134.2 (3)C3'—C2'—N1'—C6'0.1 (5)
C5'—C4'—C10'—C11'−133.5 (3)C5'—C6'—N1'—C2'2.2 (4)
C3'—C4'—C10'—C11'47.3 (4)C16'—C6'—N1'—C2'−177.0 (2)
C15—C10—C11—C12−1.8 (4)C21'—C16'—N17'—C18'0.6 (5)
C4—C10—C11—C12179.2 (3)C6'—C16'—N17'—C18'−177.2 (3)
C15'—C10'—C11'—C12'1.4 (4)C19'—C18'—N17'—C16'0.0 (6)
C4'—C10'—C11'—C12'179.9 (3)C21—C16—N17—C18−0.8 (5)
C10'—C11'—C12'—C13'0.5 (4)C6—C16—N17—C18179.2 (3)
C10—C11—C12—C13−0.6 (4)C19—C18—N17—C160.3 (6)
C11'—C12'—C13'—C14'−1.9 (5)N1—C2—O1—C7−2.6 (4)
C11'—C12'—C13'—Cl1'177.3 (2)C3—C2—O1—C7177.5 (3)
C11—C12—C13—C143.0 (5)N1'—C2'—O1'—C7'−0.1 (4)
C11—C12—C13—Cl1−177.5 (2)C3'—C2'—O1'—C7'179.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11···N9'i0.932.583.321 (4)137
C21—H21···Cl1ii0.932.803.597 (3)144
C11'—H11'···N9iii0.932.603.349 (4)138
C21'—H21'···Cl1'ii0.932.713.475 (3)140

Symmetry codes: (i) −x, y+1/2, −z+2; (ii) x−1, y, z−1; (iii) −x, y−1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2899).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst.26, 343–350.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cook, C. E., Sloan, C. D., Thomas, B. F., Navarro, H. A. (2004a). Chem. Abstr.141, 157039, 861.
  • Cook, C. E., Sloan, C. D., Thomas, B. F., Navarro, H. A. (2004b). US Patent 2004147539.
  • Ellefson, C. R., Woo, C. M. & Cusic, J. W. (1978). J. Med. Chem., 21, 340–343. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Heintzelman, G. R., Averill, K. M., Dodd, J. H., Demarest, K. T., Tang, Y., Jackson, P. F. (2003a). Chem. Abstr.139, 350637, 730.
  • Heintzelman, G. R., Averill, K. M., Dodd, J. H., Demarest, K. T., Tang, Y., Jackson, P. F. (2003b). World Patent WO 2003088963.
  • Sheldrick, G. M. (2001). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Upton, C., Osborne, R. H. & Jaffar, M. (2000). Bioorg. Med. Chem. Lett., 10, 1277–1279. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography