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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o578.
Published online 2009 February 21. doi:  10.1107/S1600536809005327
PMCID: PMC2968586

N-[Morpholino(phen­yl)meth­yl]benzamide

Abstract

The title compound, C18H20N2O2, crystallizes with two mol­ecules in the asymmetric unit. The morpholine rings of both mol­ecules adopt chair conformations. The crystal structure is stabilized by inter­molecular N—H(...)O hydrogen bonds. One phenyl ring is disordered over two orientations in a 0.665 (5):0.335 (5) ratio.

Related literature

For background literature on benzamides and morpholines, see: Carbonnelle et al. (2005 [triangle]); Hatzelmann & Schudt (2001 [triangle]); Li et al. (1998 [triangle]); Malik et al. (2006 [triangle]); Sedavkina et al. (1984 [triangle]); Simonini et al. (2006 [triangle]); Suzuki et al. (2005 [triangle]); Zhou et al. (1999); Zhou et al. (1999 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]).

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Object name is e-65-0o578-scheme1.jpg

Experimental

Crystal data

  • C18H20N2O2
  • M r = 296.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o578-efi1.jpg
  • a = 9.9190 (3) Å
  • b = 10.6793 (3) Å
  • c = 15.8050 (5) Å
  • α = 79.747 (2)°
  • β = 85.543 (1)°
  • γ = 85.467 (1)°
  • V = 1638.84 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.20 × 0.19 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.979, T max = 0.994
  • 21213 measured reflections
  • 7329 independent reflections
  • 4069 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.156
  • S = 1.03
  • 7329 reflections
  • 417 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005327/hb2906sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005327/hb2906Isup2.hkl

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

Acknowledgments

The authors thank the Department of Chemistry, IIT­Madras, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Benzamide derivatives, known for their anti-inflammatory and immunomodulatory (Hatezelmann et al., 2001; Carbonnelle et al., 2005), anti-tumoral (Suzuki et al., 2005), antipsychotic (Simonini et al., 2006), and antiallergic (Zhou et al.,1999) activities, are drugs widely used in medicine (Malik et al., 2006).

Morpholine is a multipurpose chemical which is used as a solvent for resins, dyes and waxes. One of its most important use is as a chemical intermediate in the preparation of pesticides (Li et al., 1998). A number of morpholine derivatives have been described as analgesics and local anesthetics. The morpholinomethyl derivative of pyrizinamide (morphozinamide) has been found to be more effective in the treatment of tuberculosis than pyrizinamide (Sedavkina et al., 1984).

In the title compound, (I), each of the two independent molecules contains three ring systems, one phenyl ring, one benzamide and a morpholino ring (Fig. 1).

The morpholine rings of the two molecules adopts the usual chair conformation (QT = 0.577 (2) Å, q(2)=0.012 (2)Å and q(3)=0.577 (2) Å, θ = 1.4 (2)°. (Cremer & Pople, 1975). The best planes of the rings pass through the C atoms, leaving the O and N atoms on either side. The methine (C—H) substitution (C5) of the morpholine ring is in an equatorial position. One of the benzamide moiety in the crystal structure is disordered with an occupancy factor of 0.33 and 0.67. The phenyl moiety is planar. The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds (Table 1).

Experimental

Benzamide (12.1 g, 0.1 mol) was dissolved in a minimum quantity of ethanol. To this solution, benzaldehdye (10 ml, 0.1 mol) followed by morpholine (9 ml, 0.1 mol) was added in small quantities with constant stirring in an ice bath. For about 2 hrs, the mixture was kept at ice cold temperature. After 10 days a pale yellow semi-solid was obtained. The product was purified by washing with distilled water several times and finally with 5 ml of acetone. The compound was dried in an air oven at 80° C and recrystallized from ethanol to yield colourless slabs of (I).

Refinement

One of the benzamide groups in the crystal structure is disordered with occupancy factor of 0.33 and 0.67. The H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2. The H atoms associated with nitrogen atoms were located from difference maps and refined.

Figures

Fig. 1.
The molecular structure of (I); displacement ellipsoids for the non-hydrogen atoms are drawn with 30% probability.

Crystal data

C18H20N2O2Z = 4
Mr = 296.36F(000) = 632
Triclinic, P1Dx = 1.201 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9190 (3) ÅCell parameters from 4916 reflections
b = 10.6793 (3) Åθ = 2.2–23.9°
c = 15.8050 (5) ŵ = 0.08 mm1
α = 79.747 (2)°T = 295 K
β = 85.543 (1)°Slab, colourless
γ = 85.467 (1)°0.20 × 0.19 × 0.08 mm
V = 1638.84 (9) Å3

Data collection

Bruker APEXII CCD diffractometer7329 independent reflections
Radiation source: fine-focus sealed tube4069 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 28.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −10→12
Tmin = 0.979, Tmax = 0.994k = −14→14
21213 measured reflectionsl = −20→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
7329 reflectionsΔρmax = 0.24 e Å3
417 parametersΔρmin = −0.19 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (15)

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*/UeqOcc. (<1)
H40.424 (2)0.6985 (17)0.1586 (12)0.046 (5)*
H20.920 (2)0.7527 (17)0.1718 (12)0.045 (5)*
C11.0046 (2)0.93888 (19)0.38352 (14)0.0601 (6)
H1A0.96780.90890.44160.072*
H1B1.10110.94560.38570.072*
C20.98194 (17)0.84343 (17)0.32713 (12)0.0446 (4)
H2A1.02310.87020.26970.054*
H2B1.02390.76070.35060.054*
C30.7737 (2)0.9600 (2)0.29057 (14)0.0615 (6)
H3A0.67670.95510.28930.074*
H3B0.81000.99010.23240.074*
C40.8019 (3)1.0509 (2)0.34844 (17)0.0762 (7)
H4A0.75971.13450.32720.091*
H4B0.76201.02190.40590.091*
C50.79770 (17)0.73575 (17)0.27916 (11)0.0416 (4)
H50.69840.74120.28320.050*
C60.84088 (17)0.60273 (18)0.32558 (11)0.0431 (4)
C70.8263 (2)0.5763 (2)0.41468 (13)0.0641 (6)
H70.79500.64110.44490.077*
C80.8572 (3)0.4560 (2)0.45923 (16)0.0782 (8)
H80.84760.44040.51910.094*
C90.9018 (2)0.3597 (2)0.41592 (17)0.0721 (7)
H90.92220.27810.44600.086*
C100.9165 (2)0.3834 (2)0.32819 (16)0.0655 (6)
H100.94690.31780.29850.079*
C110.88661 (19)0.5043 (2)0.28309 (13)0.0542 (5)
H110.89750.51930.22320.065*
C120.75048 (18)0.75042 (19)0.12841 (12)0.0470 (5)
C130.80194 (18)0.7748 (2)0.03612 (12)0.0501 (5)
C140.8036 (3)0.6824 (3)−0.01283 (16)0.0868 (8)
H140.77590.60200.01170.104*
C150.8471 (3)0.7081 (4)−0.1008 (2)0.1097 (12)
H150.85100.6444−0.13420.132*
C160.8837 (3)0.8282 (5)−0.13637 (18)0.1034 (11)
H160.90980.8467−0.19480.124*
C170.8821 (3)0.9187 (4)−0.0879 (2)0.1071 (11)
H170.90800.9996−0.11260.128*
C180.8423 (3)0.8927 (3)−0.00143 (16)0.0831 (8)
H180.84290.95620.03190.100*
C190.3099 (2)0.32634 (19)0.35265 (15)0.0621 (6)
H19A0.27710.33500.41090.074*
H19B0.26360.25850.33630.074*
C200.27701 (19)0.44881 (18)0.29285 (13)0.0512 (5)
H20A0.30420.43920.23390.061*
H20B0.18010.47000.29670.061*
C210.49322 (17)0.51686 (17)0.31197 (13)0.0474 (5)
H21A0.54110.58370.32840.057*
H21B0.52470.50800.25350.057*
C220.5214 (2)0.39299 (19)0.37222 (14)0.0591 (5)
H22A0.61800.37010.36950.071*
H22B0.49350.40390.43080.071*
C230.30607 (16)0.67541 (16)0.26940 (10)0.0355 (4)
H230.20680.68190.27590.043*
C240.35210 (16)0.78231 (16)0.30993 (11)0.0369 (4)
C250.36414 (19)0.90344 (17)0.26293 (12)0.0479 (5)
H250.35210.91830.20410.057*
C260.3938 (2)1.00258 (19)0.30196 (14)0.0574 (5)
H260.40071.08370.26940.069*
C270.4132 (2)0.98284 (19)0.38818 (15)0.0588 (6)
H270.43301.05010.41430.071*
C280.4031 (2)0.8632 (2)0.43562 (14)0.0618 (6)
H280.41730.84890.49410.074*
C290.3720 (2)0.76369 (18)0.39714 (12)0.0509 (5)
H290.36430.68300.43020.061*
C300.24685 (18)0.70289 (18)0.11932 (11)0.0440 (4)
C310.29382 (18)0.7137 (2)0.02652 (12)0.0536 (5)
C320.2052 (2)0.7115 (3)−0.03215 (14)0.0763 (7)
H320.11410.7053−0.01430.092*
C330.2436 (3)0.7181 (3)−0.11813 (15)0.0907 (9)
H330.18130.7438−0.15990.109*
C340.355 (2)0.6909 (19)−0.1370 (12)0.088 (3)0.337 (5)
H340.38050.6916−0.19500.105*0.337 (5)
C350.4530 (12)0.6576 (19)−0.0792 (7)0.151 (4)0.337 (5)
H350.54280.6396−0.09730.181*0.337 (5)
C360.4148 (10)0.6518 (15)0.0041 (6)0.112 (2)0.337 (5)
H360.46890.60680.04630.134*0.337 (5)
C34A0.3751 (10)0.7434 (8)−0.1504 (5)0.088 (3)0.665 (5)
H34A0.40270.7427−0.20790.105*0.665 (5)
C35A0.4608 (5)0.7689 (9)−0.0943 (3)0.151 (4)0.665 (5)
H35A0.54690.7938−0.11450.181*0.665 (5)
C36A0.4223 (4)0.7585 (7)−0.0062 (3)0.112 (2)0.665 (5)
H36A0.48090.78100.03100.134*0.665 (5)
N10.83673 (14)0.83410 (14)0.32292 (9)0.0431 (4)
N20.83821 (16)0.75434 (15)0.18720 (9)0.0433 (4)
N30.34807 (13)0.55046 (13)0.31612 (9)0.0369 (3)
N40.34120 (15)0.69325 (14)0.17671 (9)0.0397 (4)
O10.94265 (16)1.06078 (13)0.35261 (10)0.0716 (5)
O20.63267 (14)0.7272 (2)0.14833 (10)0.0927 (6)
O30.45161 (15)0.29292 (12)0.35088 (9)0.0622 (4)
O40.12536 (13)0.70222 (17)0.14163 (9)0.0694 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0634 (13)0.0525 (13)0.0676 (15)−0.0006 (10)−0.0101 (11)−0.0180 (11)
C20.0409 (10)0.0458 (11)0.0473 (11)−0.0016 (8)−0.0037 (8)−0.0086 (9)
C30.0511 (12)0.0625 (14)0.0687 (15)0.0135 (10)−0.0069 (10)−0.0117 (11)
C40.0826 (18)0.0589 (15)0.0865 (18)0.0211 (12)−0.0035 (13)−0.0233 (13)
C50.0335 (9)0.0555 (12)0.0349 (10)−0.0077 (8)0.0019 (7)−0.0050 (8)
C60.0382 (10)0.0536 (12)0.0379 (11)−0.0148 (8)−0.0018 (8)−0.0046 (9)
C70.0928 (17)0.0605 (14)0.0413 (13)−0.0270 (12)−0.0030 (11)−0.0057 (10)
C80.114 (2)0.0689 (17)0.0519 (14)−0.0410 (14)−0.0205 (13)0.0112 (13)
C90.0731 (16)0.0569 (15)0.0826 (19)−0.0201 (11)−0.0242 (13)0.0130 (13)
C100.0576 (14)0.0537 (14)0.0823 (18)−0.0037 (10)−0.0003 (11)−0.0062 (12)
C110.0490 (12)0.0623 (14)0.0494 (12)−0.0053 (9)0.0026 (9)−0.0069 (10)
C120.0378 (11)0.0611 (12)0.0406 (11)−0.0096 (8)−0.0041 (8)−0.0011 (9)
C130.0401 (11)0.0722 (14)0.0375 (11)−0.0085 (9)−0.0079 (8)−0.0037 (10)
C140.0871 (19)0.118 (2)0.0651 (17)−0.0422 (16)0.0116 (13)−0.0345 (16)
C150.086 (2)0.187 (4)0.076 (2)−0.031 (2)−0.0014 (16)−0.068 (2)
C160.078 (2)0.182 (4)0.0451 (16)−0.008 (2)−0.0085 (13)−0.002 (2)
C170.120 (3)0.116 (3)0.065 (2)−0.001 (2)0.0143 (17)0.0269 (19)
C180.104 (2)0.0780 (18)0.0583 (16)−0.0079 (14)0.0130 (14)0.0062 (13)
C190.0649 (14)0.0479 (12)0.0772 (16)−0.0198 (10)0.0078 (11)−0.0195 (11)
C200.0471 (11)0.0500 (12)0.0617 (13)−0.0137 (8)−0.0027 (9)−0.0201 (10)
C210.0392 (10)0.0445 (11)0.0569 (12)−0.0049 (8)−0.0053 (8)−0.0027 (9)
C220.0583 (13)0.0475 (12)0.0694 (14)−0.0039 (9)−0.0121 (10)−0.0006 (10)
C230.0324 (9)0.0438 (10)0.0312 (10)−0.0034 (7)−0.0008 (7)−0.0086 (8)
C240.0368 (9)0.0380 (10)0.0355 (10)−0.0018 (7)−0.0026 (7)−0.0059 (8)
C250.0562 (12)0.0446 (11)0.0407 (11)−0.0013 (8)−0.0034 (9)−0.0021 (9)
C260.0654 (14)0.0361 (11)0.0685 (15)−0.0055 (9)−0.0002 (11)−0.0042 (10)
C270.0681 (14)0.0443 (12)0.0702 (16)−0.0089 (9)−0.0114 (11)−0.0213 (11)
C280.0883 (16)0.0527 (13)0.0496 (13)−0.0093 (11)−0.0188 (11)−0.0147 (10)
C290.0737 (14)0.0408 (11)0.0395 (11)−0.0107 (9)−0.0117 (9)−0.0043 (9)
C300.0349 (10)0.0597 (12)0.0387 (11)−0.0010 (8)−0.0053 (8)−0.0112 (9)
C310.0371 (11)0.0869 (15)0.0369 (11)0.0045 (9)−0.0049 (8)−0.0139 (10)
C320.0602 (14)0.129 (2)0.0433 (14)−0.0190 (13)−0.0053 (11)−0.0173 (13)
C330.092 (2)0.142 (3)0.0416 (15)−0.0070 (18)−0.0130 (13)−0.0222 (15)
C340.075 (4)0.148 (8)0.030 (3)0.011 (5)0.008 (2)−0.001 (4)
C350.056 (2)0.341 (12)0.035 (2)−0.024 (5)0.0031 (17)0.025 (5)
C360.0525 (19)0.244 (8)0.0336 (18)−0.045 (4)−0.0036 (13)0.004 (4)
C34A0.075 (4)0.148 (8)0.030 (3)0.011 (5)0.008 (2)−0.001 (4)
C35A0.056 (2)0.341 (12)0.035 (2)−0.024 (5)0.0031 (17)0.025 (5)
C36A0.0525 (19)0.244 (8)0.0336 (18)−0.045 (4)−0.0036 (13)0.004 (4)
N10.0375 (8)0.0483 (9)0.0431 (9)−0.0001 (6)0.0002 (6)−0.0089 (7)
N20.0311 (9)0.0633 (11)0.0344 (9)−0.0083 (7)0.0000 (7)−0.0039 (7)
N30.0358 (8)0.0381 (8)0.0388 (8)−0.0082 (6)−0.0018 (6)−0.0098 (6)
N40.0307 (8)0.0575 (10)0.0313 (8)−0.0034 (7)−0.0017 (6)−0.0088 (7)
O10.0799 (11)0.0464 (9)0.0908 (12)0.0007 (7)−0.0088 (9)−0.0186 (8)
O20.0414 (9)0.184 (2)0.0517 (10)−0.0374 (10)−0.0043 (7)−0.0024 (11)
O30.0682 (10)0.0396 (8)0.0784 (11)−0.0026 (6)−0.0007 (8)−0.0117 (7)
O40.0316 (8)0.1312 (14)0.0459 (8)−0.0037 (7)−0.0032 (6)−0.0174 (9)

Geometric parameters (Å, °)

C1—O11.416 (2)C20—H20A0.9700
C1—C21.508 (3)C20—H20B0.9700
C1—H1A0.9700C21—N31.455 (2)
C1—H1B0.9700C21—C221.506 (3)
C2—N11.459 (2)C21—H21A0.9700
C2—H2A0.9700C21—H21B0.9700
C2—H2B0.9700C22—O31.420 (2)
C3—N11.460 (2)C22—H22A0.9700
C3—C41.502 (3)C22—H22B0.9700
C3—H3A0.9700C23—N31.452 (2)
C3—H3B0.9700C23—N41.461 (2)
C4—O11.416 (3)C23—C241.520 (2)
C4—H4A0.9700C23—H230.9800
C4—H4B0.9700C24—C251.381 (2)
C5—N11.448 (2)C24—C291.385 (2)
C5—N21.460 (2)C25—C261.378 (3)
C5—C61.524 (3)C25—H250.9300
C5—H50.9800C26—C271.368 (3)
C6—C111.375 (3)C26—H260.9300
C6—C71.385 (3)C27—C281.368 (3)
C7—C81.374 (3)C27—H270.9300
C7—H70.9300C28—C291.381 (3)
C8—C91.362 (4)C28—H280.9300
C8—H80.9300C29—H290.9300
C9—C101.363 (3)C30—O41.229 (2)
C9—H90.9300C30—N41.339 (2)
C10—C111.381 (3)C30—C311.491 (3)
C10—H100.9300C31—C321.331 (3)
C11—H110.9300C31—C361.376 (12)
C12—O21.219 (2)C31—C36A1.424 (5)
C12—N21.330 (2)C32—C331.373 (3)
C12—C131.492 (3)C32—H320.9300
C13—C141.357 (3)C33—C341.15 (2)
C13—C181.369 (3)C33—C34A1.392 (9)
C14—C151.408 (4)C33—H330.9300
C14—H140.9300C34—C351.37 (2)
C15—C161.370 (5)C34—H340.9300
C15—H150.9300C35—C361.334 (16)
C16—C171.334 (4)C35—H350.9300
C16—H160.9300C36—H360.9300
C17—C181.379 (4)C34A—C35A1.350 (11)
C17—H170.9300C34A—H34A0.9300
C18—H180.9300C35A—C36A1.403 (7)
C19—O31.422 (2)C35A—H35A0.9300
C19—C201.500 (3)C36A—H36A0.9300
C19—H19A0.9700N2—H20.832 (19)
C19—H19B0.9700N4—H40.855 (19)
C20—N31.454 (2)
O1—C1—C2111.83 (17)N3—C21—H21B109.9
O1—C1—H1A109.3C22—C21—H21B109.9
C2—C1—H1A109.3H21A—C21—H21B108.3
O1—C1—H1B109.3O3—C22—C21111.62 (16)
C2—C1—H1B109.3O3—C22—H22A109.3
H1A—C1—H1B107.9C21—C22—H22A109.3
N1—C2—C1109.40 (15)O3—C22—H22B109.3
N1—C2—H2A109.8C21—C22—H22B109.3
C1—C2—H2A109.8H22A—C22—H22B108.0
N1—C2—H2B109.8N3—C23—N4114.37 (13)
C1—C2—H2B109.8N3—C23—C24111.98 (13)
H2A—C2—H2B108.2N4—C23—C24112.06 (14)
N1—C3—C4109.16 (17)N3—C23—H23105.9
N1—C3—H3A109.8N4—C23—H23105.9
C4—C3—H3A109.8C24—C23—H23105.9
N1—C3—H3B109.8C25—C24—C29117.87 (16)
C4—C3—H3B109.8C25—C24—C23121.25 (15)
H3A—C3—H3B108.3C29—C24—C23120.65 (15)
O1—C4—C3111.84 (17)C26—C25—C24120.91 (18)
O1—C4—H4A109.2C26—C25—H25119.5
C3—C4—H4A109.2C24—C25—H25119.5
O1—C4—H4B109.2C27—C26—C25120.60 (19)
C3—C4—H4B109.2C27—C26—H26119.7
H4A—C4—H4B107.9C25—C26—H26119.7
N1—C5—N2114.34 (14)C26—C27—C28119.35 (19)
N1—C5—C6111.81 (14)C26—C27—H27120.3
N2—C5—C6112.37 (15)C28—C27—H27120.3
N1—C5—H5105.8C27—C28—C29120.38 (19)
N2—C5—H5105.8C27—C28—H28119.8
C6—C5—H5105.8C29—C28—H28119.8
C11—C6—C7117.72 (19)C28—C29—C24120.88 (18)
C11—C6—C5123.12 (16)C28—C29—H29119.6
C7—C6—C5119.05 (17)C24—C29—H29119.6
C8—C7—C6121.2 (2)O4—C30—N4121.70 (16)
C8—C7—H7119.4O4—C30—C31120.55 (15)
C6—C7—H7119.4N4—C30—C31117.75 (15)
C9—C8—C7120.2 (2)C32—C31—C36109.8 (4)
C9—C8—H8119.9C32—C31—C36A115.7 (2)
C7—C8—H8119.9C36—C31—C36A47.6 (5)
C8—C9—C10119.6 (2)C32—C31—C30120.02 (18)
C8—C9—H9120.2C36—C31—C30119.3 (4)
C10—C9—H9120.2C36A—C31—C30122.4 (2)
C9—C10—C11120.5 (2)C31—C32—C33122.3 (2)
C9—C10—H10119.8C31—C32—H32118.8
C11—C10—H10119.8C33—C32—H32118.8
C6—C11—C10120.8 (2)C34—C33—C32118.1 (10)
C6—C11—H11119.6C34—C33—C34A25.3 (11)
C10—C11—H11119.6C32—C33—C34A121.5 (4)
O2—C12—N2121.92 (17)C34—C33—H33121.0
O2—C12—C13120.76 (16)C32—C33—H33121.0
N2—C12—C13117.31 (16)C34A—C33—H33111.7
C14—C13—C18119.0 (2)C33—C34—C35123.9 (17)
C14—C13—C12120.5 (2)C33—C34—H34118.1
C18—C13—C12120.4 (2)C35—C34—H34118.1
C13—C14—C15120.1 (3)C36—C35—C34117.6 (13)
C13—C14—H14120.0C36—C35—H35121.2
C15—C14—H14120.0C34—C35—H35121.2
C16—C15—C14119.1 (3)C35—C36—C31118.8 (10)
C16—C15—H15120.4C35—C36—H36120.6
C14—C15—H15120.4C31—C36—H36120.6
C17—C16—C15120.6 (3)C35A—C34A—C33117.0 (6)
C17—C16—H16119.7C35A—C34A—H34A121.5
C15—C16—H16119.7C33—C34A—H34A121.5
C16—C17—C18120.3 (3)C34A—C35A—C36A121.2 (5)
C16—C17—H17119.9C34A—C35A—H35A119.4
C18—C17—H17119.9C36A—C35A—H35A119.4
C13—C18—C17120.9 (3)C35A—C36A—C31120.1 (4)
C13—C18—H18119.5C35A—C36A—H36A119.9
C17—C18—H18119.5C31—C36A—H36A119.9
O3—C19—C20111.83 (16)C5—N1—C2116.27 (13)
O3—C19—H19A109.2C5—N1—C3113.02 (14)
C20—C19—H19A109.2C2—N1—C3109.35 (15)
O3—C19—H19B109.2C12—N2—C5121.87 (15)
C20—C19—H19B109.2C12—N2—H2118.1 (13)
H19A—C19—H19B107.9C5—N2—H2118.9 (13)
N3—C20—C19109.53 (16)C23—N3—C20112.69 (13)
N3—C20—H20A109.8C23—N3—C21115.67 (13)
C19—C20—H20A109.8C20—N3—C21109.49 (14)
N3—C20—H20B109.8C30—N4—C23121.95 (15)
C19—C20—H20B109.8C30—N4—H4119.0 (12)
H20A—C20—H20B108.2C23—N4—H4119.0 (12)
N3—C21—C22109.04 (15)C4—O1—C1109.36 (17)
N3—C21—H21A109.9C22—O3—C19109.97 (14)
C22—C21—H21A109.9
O1—C1—C2—N1−58.3 (2)C36A—C31—C32—C3317.0 (5)
N1—C3—C4—O159.2 (2)C30—C31—C32—C33−178.5 (2)
N1—C5—C6—C11−142.89 (17)C31—C32—C33—C3420.9 (12)
N2—C5—C6—C11−12.8 (2)C31—C32—C33—C34A−8.1 (6)
N1—C5—C6—C741.1 (2)C32—C33—C34—C35−3(2)
N2—C5—C6—C7171.26 (16)C34A—C33—C34—C35102 (4)
C11—C6—C7—C80.4 (3)C33—C34—C35—C363(3)
C5—C6—C7—C8176.60 (19)C34—C35—C36—C31−19 (2)
C6—C7—C8—C9−0.7 (4)C32—C31—C36—C3532.9 (13)
C7—C8—C9—C100.4 (4)C36A—C31—C36—C35−74.3 (12)
C8—C9—C10—C110.1 (3)C30—C31—C36—C35177.1 (10)
C7—C6—C11—C100.1 (3)C34—C33—C34A—C35A−94 (3)
C5—C6—C11—C10−175.94 (17)C32—C33—C34A—C35A−4.0 (10)
C9—C10—C11—C6−0.3 (3)C33—C34A—C35A—C36A5.8 (12)
O2—C12—C13—C14−63.2 (3)C34A—C35A—C36A—C313.5 (11)
N2—C12—C13—C14116.4 (2)C32—C31—C36A—C35A−14.8 (7)
O2—C12—C13—C18113.7 (3)C36—C31—C36A—C35A79.2 (9)
N2—C12—C13—C18−66.6 (3)C30—C31—C36A—C35A−178.9 (5)
C18—C13—C14—C150.4 (4)N2—C5—N1—C2−65.13 (19)
C12—C13—C14—C15177.4 (2)C6—C5—N1—C263.99 (19)
C13—C14—C15—C16−1.9 (4)N2—C5—N1—C362.6 (2)
C14—C15—C16—C172.0 (5)C6—C5—N1—C3−168.34 (15)
C15—C16—C17—C18−0.6 (5)C1—C2—N1—C5−173.23 (15)
C14—C13—C18—C171.0 (4)C1—C2—N1—C357.3 (2)
C12—C13—C18—C17−176.0 (2)C4—C3—N1—C5171.06 (17)
C16—C17—C18—C13−0.9 (4)C4—C3—N1—C2−57.7 (2)
O3—C19—C20—N3−57.9 (2)O2—C12—N2—C5−2.3 (3)
N3—C21—C22—O358.8 (2)C13—C12—N2—C5178.09 (16)
N3—C23—C24—C25158.18 (15)N1—C5—N2—C12−128.73 (18)
N4—C23—C24—C2528.1 (2)C6—C5—N2—C12102.44 (19)
N3—C23—C24—C29−27.4 (2)N4—C23—N3—C20−66.05 (18)
N4—C23—C24—C29−157.45 (16)C24—C23—N3—C20165.10 (14)
C29—C24—C25—C26−0.6 (3)N4—C23—N3—C2160.98 (18)
C23—C24—C25—C26173.99 (17)C24—C23—N3—C21−67.87 (18)
C24—C25—C26—C270.6 (3)C19—C20—N3—C23−171.53 (15)
C25—C26—C27—C280.1 (3)C19—C20—N3—C2158.23 (19)
C26—C27—C28—C29−0.8 (3)C22—C21—N3—C23172.89 (15)
C27—C28—C29—C240.8 (3)C22—C21—N3—C20−58.5 (2)
C25—C24—C29—C28−0.1 (3)O4—C30—N4—C232.9 (3)
C23—C24—C29—C28−174.71 (18)C31—C30—N4—C23−176.67 (16)
O4—C30—C31—C32−5.8 (3)N3—C23—N4—C30110.43 (18)
N4—C30—C31—C32173.7 (2)C24—C23—N4—C30−120.76 (18)
O4—C30—C31—C36−146.4 (7)C3—C4—O1—C1−58.9 (2)
N4—C30—C31—C3633.2 (7)C2—C1—O1—C458.3 (2)
O4—C30—C31—C36A157.7 (4)C21—C22—O3—C19−57.6 (2)
N4—C30—C31—C36A−22.7 (4)C20—C19—O3—C2257.2 (2)
C36—C31—C32—C33−34.5 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O20.85 (2)2.11 (2)2.932 (2)163.5 (17)
N2—H2···O4i0.832 (19)2.10 (2)2.918 (2)166.5 (17)

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2906).

References

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