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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1822.
Published online 2010 June 26. doi:  10.1107/S1600536810024396
PMCID: PMC3007005

3-[(3S)-3-Ethyl-1-methyl­azepan-3-yl]phenyl N-(4-fluoro­phen­yl)carbamate

Abstract

The asymmetric unit of the title compound, C22H27FN2O2, a (−)-S-meptazinol derivative, contains two mol­ecules. The azepane ring adopts a similar twist chair form in both mol­ecules, while the dihedral angles between the two benzene rings are 88.17 (14) and 89.93 (14)° in the two mol­ecules. The absolute configuration of the mol­ecule was determined from the synthetic starting material. The crystal structure is stabilized by classical inter­molecular N—H(...)O hydrogen bonds.

Related literature

For a related structure, see: Ennis et al. (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1822-scheme1.jpg

Experimental

Crystal data

  • C22H27FN2O2
  • M r = 370.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1822-efi1.jpg
  • a = 11.3836 (17) Å
  • b = 9.7368 (15) Å
  • c = 19.008 (3) Å
  • β = 105.564 (3)°
  • V = 2029.6 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.30 × 0.28 × 0.21 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.565, T max = 1.000
  • 10768 measured reflections
  • 7172 independent reflections
  • 3625 reflections with I > 2σ(I)
  • R int = 0.092

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.134
  • S = 0.83
  • 7172 reflections
  • 437 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024396/rk2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024396/rk2204Isup2.hkl

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

Acknowledgments

This work was funded in part by the National Natural Science Foundation of China (grant No. 30801435).

supplementary crystallographic information

Comment

(-)–Meptazinol is a moderate AChE inhibitor (Ennis et al., 1986). Its absolute configuration was determined as S by X–ray crystal structures. The title compound is derived from (-)–S–meptazinol. We report here the molecular structure of the title compound in order to study the relationship between its structure and AChE inhibitory activity.

The molecular structure of the title compound presented on Fig. 1. The asymmetric unit has two molecules. The azepane ring adopts a similar twist chair form in both molecules. The dihedral angle between of two benzene rings is 88.17 (14)° and 89.93 (14)° in the first and second molecules respectively. The crystal structure is stabilized by classical intermolecular hydrogen bonds - N3—H3A···O3i and N1—H1···O1ii. Symmetry codes: (i) -x+1, y+1/2, -z; (ii) -x+1, y-1/2, -z+1.

The absolute configuration of the azepane ring atom is C14(S), since the title compound was synthesized from (-)–S–meptazinol by esterification of the phenol group, which does not interfere with the chiral center C14.

Experimental

(-)–Meptazinol (200 mg, 0.86 mmol) was dissolved in anhydrous ether (5 ml) and a piece of Na metal (approximately 10 mg) was added. The mixture was stirred at room temperature for 30 min. Then 4–fluorophenylisocyanate (230 mg, 1.72 mmol) was added. The reaction mixture was continuously stirred for 4 h at room temperature and monitored by TLC. The precipitate was filtered off and the filtrate was evaporated to give yellow oil. The 10 ml H2O was added and pH of the aqueous layer was adjusted to 3 by 1N HCl, washed with Et2O, and then pH was adjusted to 10 by saturated Na2CO3 aqueous solution. The resulting precipitate was filtered and washed with water three times. A white solid (yield 200 mg, 65.5%) was obtained. Single crystals suitable for X–ray analysis were obtained by slow evaporation of an acetonitrile solution.

Refinement

All H atoms were placed in the idealized positions with C—H = 0.93–0.96Å, and N—H = 0.86Å. The Uiso(H) = 1.2–1.5 Ueq(C,N).

The 3164 Friedel pairs were merged in crystal refinement procedure.

Figures

Fig. 1.
The molecular structure of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

C22H27FN2O2F(000) = 792
Mr = 370.46Dx = 1.212 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1695 reflections
a = 11.3836 (17) Åθ = 4.5–41.4°
b = 9.7368 (15) ŵ = 0.08 mm1
c = 19.008 (3) ÅT = 295 K
β = 105.564 (3)°Prism, colourless
V = 2029.6 (5) Å30.30 × 0.28 × 0.21 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer7172 independent reflections
Radiation source: fine–focus sealed tube3625 reflections with I > 2σ(I)
graphiteRint = 0.092
[var phi] and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→10
Tmin = 0.565, Tmax = 1.000k = −11→11
10768 measured reflectionsl = −23→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.83w = 1/[σ2(Fo2) + (0.0436P)2] where P = (Fo2 + 2Fc2)/3
7172 reflections(Δ/σ)max = 0.041
437 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = −0.20 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
F10.0700 (2)0.6112 (3)0.22631 (14)0.0913 (10)
F20.0725 (2)0.3412 (3)−0.27982 (14)0.0860 (10)
N10.4300 (3)0.4547 (4)0.46958 (18)0.0523 (10)
H10.43840.36710.47410.063*
N20.7713 (4)0.3080 (5)0.9169 (2)0.0838 (12)
N30.4376 (3)0.4940 (4)−0.03739 (18)0.0496 (10)
H3A0.45110.5810−0.03440.060*
N40.8545 (5)0.6054 (5)0.4366 (2)0.0949 (15)
O10.5086 (3)0.6544 (3)0.52648 (15)0.0577 (8)
O20.5776 (3)0.4446 (3)0.57009 (16)0.0688 (10)
O30.5055 (3)0.2960 (3)0.02499 (16)0.0618 (9)
O40.5764 (3)0.5055 (3)0.06587 (15)0.0621 (9)
C10.5050 (4)0.5303 (5)0.5213 (2)0.0454 (12)
C20.3388 (2)0.5017 (3)0.40860 (12)0.0481 (11)
C30.2979 (2)0.4082 (2)0.35204 (15)0.0642 (14)
H30.33150.32060.35550.077*
C40.2069 (3)0.4458 (3)0.29030 (13)0.0732 (15)
H40.17960.38320.25250.088*
C50.1568 (2)0.5767 (3)0.28511 (13)0.0612 (13)
C60.1976 (3)0.6702 (3)0.34168 (17)0.0723 (15)
H60.16410.75780.33820.087*
C70.2887 (3)0.6327 (2)0.40342 (14)0.0677 (14)
H70.31600.69520.44130.081*
C80.6717 (2)0.5014 (3)0.62384 (13)0.0554 (13)
C90.6660 (2)0.4941 (3)0.69589 (15)0.0533 (12)
H90.59590.46160.70650.064*
C100.7652 (2)0.5355 (3)0.75212 (11)0.0478 (11)
C110.8701 (2)0.5841 (3)0.73631 (12)0.0537 (12)
H110.93650.61170.77390.064*
C120.8758 (2)0.5913 (3)0.66426 (14)0.0598 (12)
H120.94600.62380.65370.072*
C130.7766 (3)0.5500 (3)0.60803 (11)0.0590 (13)
H130.78040.55480.55980.071*
C140.7592 (4)0.5133 (5)0.8317 (2)0.0515 (12)
C150.8710 (3)0.5714 (5)0.8876 (2)0.0607 (11)
H15A0.89060.65960.86990.073*
H15B0.84890.58810.93270.073*
C160.9848 (4)0.4843 (5)0.9051 (2)0.0815 (14)
H16A1.05560.54370.91910.098*
H16B0.98880.43450.86160.098*
C170.9890 (5)0.3816 (7)0.9667 (3)0.106 (2)
H17A1.07020.34240.98190.128*
H17B0.97530.43111.00810.128*
C180.8995 (6)0.2677 (7)0.9479 (3)0.110 (2)
H18A0.92320.20800.91330.132*
H18B0.90470.21440.99180.132*
C190.7500 (4)0.3574 (4)0.8414 (2)0.0680 (12)
H19A0.66930.32790.81400.082*
H19B0.80840.31300.81990.082*
C200.6444 (4)0.5822 (5)0.8442 (2)0.0762 (13)
H20A0.57340.54190.81050.091*
H20B0.64030.56000.89330.091*
C210.6361 (5)0.7371 (6)0.8352 (3)0.102 (2)
H21A0.70190.77950.87110.153*
H21B0.55970.76860.84160.153*
H21C0.64150.76130.78720.153*
C220.6905 (6)0.1909 (6)0.9190 (3)0.134 (3)
H22A0.60710.22010.90270.200*
H22B0.70700.15680.96810.200*
H22C0.70480.11930.88750.200*
C230.5058 (4)0.4166 (5)0.0171 (2)0.0467 (12)
C240.34645 (13)0.44849 (16)−0.09893 (8)0.0438 (11)
C250.30502 (17)0.54244 (19)−0.15519 (9)0.0586 (13)
H250.33890.6299−0.15170.070*
C260.21302 (16)0.5056 (2)−0.21660 (9)0.0610 (13)
H260.18530.5685−0.25420.073*
C270.16244 (15)0.3748 (2)−0.22176 (9)0.0600 (13)
C280.20387 (17)0.2809 (2)−0.16550 (10)0.0635 (13)
H280.17000.1934−0.16890.076*
C290.29587 (14)0.31772 (18)−0.10409 (9)0.0564 (13)
H290.32360.2549−0.06640.068*
C300.66943 (14)0.45063 (17)0.12176 (8)0.0514 (12)
C310.65863 (16)0.4641 (2)0.19300 (8)0.0484 (11)
H310.58690.49860.20070.058*
C320.75469 (17)0.4260 (3)0.25286 (8)0.0482 (11)
C330.85861 (16)0.3738 (2)0.23791 (9)0.0550 (12)
H330.92440.34770.27630.066*
C340.86610 (14)0.3595 (3)0.16610 (10)0.0638 (14)
H340.93660.32350.15740.077*
C350.77123 (13)0.3978 (2)0.10837 (9)0.0619 (14)
H350.77670.38770.06070.074*
C360.7499 (4)0.4493 (5)0.3320 (2)0.0539 (12)
C370.6310 (4)0.5130 (5)0.3376 (2)0.0749 (14)
H37A0.56440.46750.30270.090*
H37B0.62180.49400.38590.090*
C380.6175 (5)0.6667 (6)0.3245 (3)0.1006 (18)
H38A0.53190.68900.30510.121*
H38B0.65950.69310.28840.121*
C390.6695 (7)0.7485 (7)0.3945 (4)0.131 (3)
H39A0.64490.84360.38500.157*
H39B0.63200.71480.43130.157*
C400.8052 (7)0.7452 (8)0.4260 (3)0.130 (3)
H40A0.84340.79440.39370.156*
H40B0.82580.79240.47270.156*
C410.8602 (4)0.5406 (5)0.3668 (2)0.0755 (14)
H41A0.93370.48550.37570.091*
H41B0.86600.61230.33250.091*
C420.7673 (4)0.3108 (5)0.3736 (2)0.0724 (13)
H42A0.84100.26760.36790.087*
H42B0.77960.32960.42520.087*
C430.6628 (5)0.2097 (6)0.3495 (3)0.0982 (18)
H43A0.59140.24660.36020.147*
H43B0.68450.12450.37510.147*
H43C0.64650.19410.29790.147*
C440.9806 (6)0.6096 (9)0.4861 (3)0.158 (4)
H44A1.01200.51780.49460.236*
H44B0.97910.65100.53170.236*
H44C1.03200.66270.46370.236*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0796 (19)0.085 (2)0.082 (2)−0.0066 (17)−0.0250 (16)0.0215 (17)
F20.0722 (18)0.099 (3)0.0657 (17)0.0042 (17)−0.0175 (14)−0.0239 (17)
N10.067 (3)0.035 (2)0.047 (2)−0.005 (2)0.0016 (19)0.0007 (19)
N20.120 (4)0.083 (3)0.060 (3)−0.004 (3)0.045 (2)0.011 (2)
N30.059 (2)0.041 (2)0.043 (2)−0.0008 (19)0.0033 (18)−0.0024 (19)
N40.138 (4)0.102 (4)0.057 (3)−0.050 (3)0.046 (3)−0.032 (3)
O10.067 (2)0.044 (2)0.0513 (19)−0.0015 (17)−0.0030 (15)−0.0011 (17)
O20.080 (2)0.050 (2)0.056 (2)−0.0115 (19)−0.0161 (17)0.0050 (18)
O30.077 (2)0.035 (2)0.066 (2)−0.0006 (18)0.0044 (17)0.0030 (17)
O40.080 (2)0.038 (2)0.0494 (19)0.0007 (18)−0.0150 (16)0.0000 (17)
C10.055 (3)0.036 (3)0.043 (3)0.002 (3)0.011 (2)0.007 (2)
C20.050 (3)0.043 (3)0.049 (3)−0.005 (2)0.010 (2)0.003 (2)
C30.065 (3)0.056 (3)0.059 (3)0.010 (3)−0.005 (2)−0.007 (3)
C40.076 (4)0.076 (4)0.055 (3)−0.001 (3)−0.005 (3)−0.018 (3)
C50.053 (3)0.068 (4)0.049 (3)−0.012 (3)−0.010 (2)0.019 (3)
C60.068 (3)0.058 (4)0.072 (3)−0.001 (3)−0.014 (3)0.007 (3)
C70.073 (3)0.052 (4)0.069 (3)0.000 (3)0.003 (3)−0.006 (3)
C80.060 (3)0.043 (3)0.055 (3)−0.005 (2)0.001 (3)0.010 (3)
C90.050 (3)0.057 (3)0.053 (3)−0.007 (2)0.013 (2)0.007 (2)
C100.056 (3)0.043 (3)0.047 (3)0.005 (2)0.016 (2)0.002 (2)
C110.056 (3)0.060 (3)0.045 (3)−0.008 (2)0.015 (2)0.007 (2)
C120.055 (3)0.073 (3)0.050 (3)−0.007 (3)0.013 (2)0.008 (3)
C130.078 (3)0.056 (3)0.044 (3)0.003 (3)0.017 (3)0.005 (2)
C140.050 (3)0.055 (3)0.053 (3)−0.006 (2)0.019 (2)−0.005 (2)
C150.067 (3)0.078 (3)0.040 (2)−0.006 (3)0.019 (2)−0.006 (2)
C160.076 (3)0.117 (4)0.053 (3)0.004 (3)0.019 (2)0.008 (3)
C170.109 (5)0.149 (6)0.063 (4)0.036 (4)0.026 (3)0.026 (4)
C180.175 (7)0.102 (5)0.066 (4)0.043 (5)0.054 (4)0.034 (4)
C190.090 (3)0.067 (3)0.048 (3)−0.005 (3)0.020 (2)0.003 (2)
C200.067 (3)0.098 (4)0.071 (3)0.000 (3)0.033 (2)−0.002 (3)
C210.120 (4)0.103 (5)0.095 (4)0.043 (4)0.050 (3)0.003 (4)
C220.229 (7)0.078 (4)0.131 (5)−0.041 (5)0.113 (5)−0.002 (4)
C230.057 (3)0.038 (3)0.041 (3)0.004 (3)0.006 (2)0.002 (2)
C240.049 (3)0.035 (3)0.045 (2)0.003 (2)0.008 (2)−0.003 (2)
C250.065 (3)0.053 (3)0.053 (3)0.005 (3)0.007 (2)0.006 (2)
C260.060 (3)0.073 (4)0.043 (3)0.008 (3)0.003 (2)0.009 (3)
C270.048 (3)0.062 (4)0.068 (3)0.006 (3)0.012 (3)−0.005 (3)
C280.059 (3)0.045 (3)0.080 (4)−0.005 (3)0.007 (3)−0.007 (3)
C290.063 (3)0.044 (3)0.052 (3)0.003 (3)−0.002 (2)0.005 (2)
C300.065 (3)0.038 (3)0.046 (3)−0.003 (2)0.007 (2)0.004 (2)
C310.048 (3)0.045 (3)0.050 (3)−0.003 (2)0.010 (2)−0.001 (2)
C320.049 (3)0.047 (3)0.046 (3)0.002 (2)0.009 (2)0.002 (2)
C330.045 (3)0.067 (3)0.047 (3)0.008 (2)0.001 (2)0.007 (2)
C340.062 (3)0.078 (4)0.058 (3)0.010 (3)0.028 (2)−0.013 (3)
C350.081 (4)0.064 (4)0.039 (3)0.000 (3)0.013 (2)−0.010 (2)
C360.068 (3)0.060 (3)0.040 (2)−0.007 (3)0.024 (2)−0.003 (2)
C370.099 (4)0.076 (4)0.062 (3)0.005 (3)0.044 (3)0.005 (3)
C380.143 (5)0.090 (4)0.094 (4)0.038 (4)0.074 (4)0.013 (3)
C390.238 (8)0.078 (5)0.111 (6)0.005 (6)0.107 (6)−0.015 (4)
C400.232 (9)0.095 (6)0.086 (5)−0.071 (6)0.084 (6)−0.046 (4)
C410.094 (4)0.093 (4)0.045 (3)−0.018 (3)0.028 (2)−0.017 (2)
C420.096 (4)0.074 (3)0.052 (3)0.011 (3)0.028 (2)0.008 (2)
C430.141 (5)0.070 (4)0.101 (4)−0.017 (4)0.062 (4)0.010 (3)
C440.137 (5)0.272 (11)0.069 (4)−0.103 (6)0.036 (4)−0.063 (5)

Geometric parameters (Å, °)

F1—C51.321 (3)C19—H19B0.9700
F2—C271.329 (3)C20—C211.518 (7)
N1—C11.336 (5)C20—H20A0.9700
N1—C21.409 (4)C20—H20B0.9700
N1—H10.8600C21—H21A0.9600
N2—C191.469 (5)C21—H21B0.9600
N2—C221.472 (6)C21—H21C0.9600
N2—C181.472 (6)C22—H22A0.9600
N3—C231.346 (5)C22—H22B0.9600
N3—C241.411 (4)C22—H22C0.9600
N3—H3A0.8600C24—C251.3900
N4—C401.465 (8)C24—C291.3900
N4—C411.485 (5)C25—C261.3900
N4—C441.491 (7)C25—H250.9300
O1—C11.213 (5)C26—C271.3900
O2—C11.353 (5)C26—H260.9300
O2—C81.382 (3)C27—C281.3900
O3—C231.184 (5)C28—C291.3900
O4—C231.361 (5)C28—H280.9300
O4—C301.390 (3)C29—H290.9300
C2—C31.3900C30—C351.3530
C2—C71.3900C30—C311.3982
C3—C41.3900C31—C321.3999
C3—H30.9300C31—H310.9300
C4—C51.3900C32—C331.3855
C4—H40.9300C32—C361.537 (4)
C5—C61.3900C33—C341.3974
C6—C71.3900C33—H330.9300
C6—H60.9300C34—C351.3688
C7—H70.9300C34—H340.9300
C8—C91.3900C35—H350.9300
C8—C131.3900C36—C371.519 (6)
C9—C101.3900C36—C411.536 (6)
C9—H90.9300C36—C421.549 (6)
C10—C111.3900C37—C381.518 (6)
C10—C141.548 (4)C37—H37A0.9700
C11—C121.3900C37—H37B0.9700
C11—H110.9300C38—C391.527 (7)
C12—C131.3900C38—H38A0.9700
C12—H120.9300C38—H38B0.9700
C13—H130.9300C39—C401.500 (8)
C14—C151.531 (5)C39—H39A0.9700
C14—C191.537 (6)C39—H39B0.9700
C14—C201.543 (5)C40—H40A0.9700
C15—C161.509 (5)C40—H40B0.9700
C15—H15A0.9700C41—H41A0.9700
C15—H15B0.9700C41—H41B0.9700
C16—C171.530 (7)C42—C431.517 (6)
C16—H16A0.9700C42—H42A0.9700
C16—H16B0.9700C42—H42B0.9700
C17—C181.483 (8)C43—H43A0.9600
C17—H17A0.9700C43—H43B0.9600
C17—H17B0.9700C43—H43C0.9600
C18—H18A0.9700C44—H44A0.9600
C18—H18B0.9700C44—H44B0.9600
C19—H19A0.9700C44—H44C0.9600
C1—N1—C2127.6 (4)H21B—C21—H21C109.5
C1—N1—H1116.2N2—C22—H22A109.5
C2—N1—H1116.2N2—C22—H22B109.5
C19—N2—C22109.8 (4)H22A—C22—H22B109.5
C19—N2—C18111.4 (4)N2—C22—H22C109.5
C22—N2—C18110.0 (5)H22A—C22—H22C109.5
C23—N3—C24127.4 (4)H22B—C22—H22C109.5
C23—N3—H3A116.3O3—C23—N3129.1 (5)
C24—N3—H3A116.3O3—C23—O4124.5 (4)
C40—N4—C41112.3 (5)N3—C23—O4106.4 (4)
C40—N4—C44109.2 (5)C25—C24—C29120.0
C41—N4—C44108.0 (5)C25—C24—N3116.98 (16)
C1—O2—C8118.0 (3)C29—C24—N3123.00 (16)
C23—O4—C30117.7 (3)C26—C25—C24120.0
O1—C1—N1127.6 (4)C26—C25—H25120.0
O1—C1—O2123.9 (5)C24—C25—H25120.0
N1—C1—O2108.5 (4)C25—C26—C27120.0
C3—C2—C7120.0C25—C26—H26120.0
C3—C2—N1116.3 (2)C27—C26—H26120.0
C7—C2—N1123.6 (2)F2—C27—C28120.20 (19)
C2—C3—C4120.0F2—C27—C26119.78 (19)
C2—C3—H3120.0C28—C27—C26120.0
C4—C3—H3120.0C27—C28—C29120.0
C5—C4—C3120.0C27—C28—H28120.0
C5—C4—H4120.0C29—C28—H28120.0
C3—C4—H4120.0C28—C29—C24120.0
F1—C5—C6120.5 (3)C28—C29—H29120.0
F1—C5—C4119.5 (3)C24—C29—H29120.0
C6—C5—C4120.0C35—C30—O4121.16 (14)
C7—C6—C5120.0C35—C30—C31121.3
C7—C6—H6120.0O4—C30—C31117.23 (14)
C5—C6—H6120.0C30—C31—C32120.7
C6—C7—C2120.0C30—C31—H31119.7
C6—C7—H7120.0C32—C31—H31119.7
C2—C7—H7120.0C33—C32—C31117.0
O2—C8—C9118.5 (2)C33—C32—C36120.75 (19)
O2—C8—C13121.1 (2)C31—C32—C36122.1 (2)
C9—C8—C13120.0C32—C33—C34121.1
C8—C9—C10120.0C32—C33—H33119.5
C8—C9—H9120.0C34—C33—H33119.5
C10—C9—H9120.0C35—C34—C33120.9
C9—C10—C11120.0C35—C34—H34119.5
C9—C10—C14118.1 (2)C33—C34—H34119.5
C11—C10—C14121.7 (2)C30—C35—C34119.0
C12—C11—C10120.0C30—C35—H35120.5
C12—C11—H11120.0C34—C35—H35120.5
C10—C11—H11120.0C37—C36—C32113.3 (3)
C11—C12—C13120.0C37—C36—C41112.0 (4)
C11—C12—H12120.0C32—C36—C41105.5 (3)
C13—C12—H12120.0C37—C36—C42108.3 (3)
C12—C13—C8120.0C32—C36—C42109.8 (3)
C12—C13—H13120.0C41—C36—C42107.8 (4)
C8—C13—H13120.0C38—C37—C36116.4 (4)
C15—C14—C19110.6 (4)C38—C37—H37A108.2
C15—C14—C20108.3 (3)C36—C37—H37A108.2
C19—C14—C20108.9 (4)C38—C37—H37B108.2
C15—C14—C10112.4 (3)C36—C37—H37B108.2
C19—C14—C10106.1 (3)H37A—C37—H37B107.4
C20—C14—C10110.6 (3)C37—C38—C39111.9 (5)
C16—C15—C14116.8 (4)C37—C38—H38A109.2
C16—C15—H15A108.1C39—C38—H38A109.2
C14—C15—H15A108.1C37—C38—H38B109.2
C16—C15—H15B108.1C39—C38—H38B109.2
C14—C15—H15B108.1H38A—C38—H38B107.9
H15A—C15—H15B107.3C40—C39—C38117.0 (5)
C15—C16—C17112.6 (4)C40—C39—H39A108.0
C15—C16—H16A109.1C38—C39—H39A108.0
C17—C16—H16A109.1C40—C39—H39B108.1
C15—C16—H16B109.1C38—C39—H39B108.1
C17—C16—H16B109.1H39A—C39—H39B107.3
H16A—C16—H16B107.8N4—C40—C39113.0 (6)
C18—C17—C16115.2 (4)N4—C40—H40A109.0
C18—C17—H17A108.5C39—C40—H40A109.0
C16—C17—H17A108.5N4—C40—H40B109.0
C18—C17—H17B108.5C39—C40—H40B109.0
C16—C17—H17B108.5H40A—C40—H40B107.8
H17A—C17—H17B107.5N4—C41—C36113.8 (3)
N2—C18—C17116.1 (6)N4—C41—H41A108.8
N2—C18—H18A108.3C36—C41—H41A108.8
C17—C18—H18A108.3N4—C41—H41B108.8
N2—C18—H18B108.3C36—C41—H41B108.8
C17—C18—H18B108.3H41A—C41—H41B107.7
H18A—C18—H18B107.4C43—C42—C36115.3 (4)
N2—C19—C14116.2 (4)C43—C42—H42A108.4
N2—C19—H19A108.2C36—C42—H42A108.4
C14—C19—H19A108.2C43—C42—H42B108.4
N2—C19—H19B108.2C36—C42—H42B108.4
C14—C19—H19B108.2H42A—C42—H42B107.5
H19A—C19—H19B107.4C42—C43—H43A109.5
C21—C20—C14116.3 (4)C42—C43—H43B109.5
C21—C20—H20A108.2H43A—C43—H43B109.5
C14—C20—H20A108.2C42—C43—H43C109.5
C21—C20—H20B108.2H43A—C43—H43C109.5
C14—C20—H20B108.2H43B—C43—H43C109.5
H20A—C20—H20B107.4N4—C44—H44A109.5
C20—C21—H21A109.5N4—C44—H44B109.5
C20—C21—H21B109.5H44A—C44—H44B109.5
H21A—C21—H21B109.5N4—C44—H44C109.5
C20—C21—H21C109.5H44A—C44—H44C109.5
H21A—C21—H21C109.5H44B—C44—H44C109.5
C2—N1—C1—O11.0 (7)C24—N3—C23—O31.0 (7)
C2—N1—C1—O2179.4 (3)C24—N3—C23—O4−176.9 (3)
C8—O2—C1—O1−8.6 (6)C30—O4—C23—O312.0 (6)
C8—O2—C1—N1172.8 (3)C30—O4—C23—N3−169.9 (3)
C1—N1—C2—C3161.6 (3)C23—N3—C24—C25−167.6 (3)
C1—N1—C2—C7−19.3 (5)C23—N3—C24—C2914.2 (4)
C7—C2—C3—C40.0C29—C24—C25—C260.0
N1—C2—C3—C4179.1 (3)N3—C24—C25—C26−178.30 (16)
C2—C3—C4—C50.0C24—C25—C26—C270.0
C3—C4—C5—F1−179.8 (3)C25—C26—C27—F2178.44 (18)
C3—C4—C5—C60.0C25—C26—C27—C280.0
F1—C5—C6—C7179.8 (3)F2—C27—C28—C29−178.43 (18)
C4—C5—C6—C70.0C26—C27—C28—C290.0
C5—C6—C7—C20.0C27—C28—C29—C240.0
C3—C2—C7—C60.0C25—C24—C29—C280.0
N1—C2—C7—C6−179.1 (3)N3—C24—C29—C28178.19 (17)
C1—O2—C8—C9112.9 (3)C23—O4—C30—C3572.2 (3)
C1—O2—C8—C13−74.7 (4)C23—O4—C30—C31−113.7 (3)
O2—C8—C9—C10172.4 (3)C35—C30—C31—C321.6
C13—C8—C9—C100.0O4—C30—C31—C32−172.52 (15)
C8—C9—C10—C110.0C30—C31—C32—C33−0.8
C8—C9—C10—C14−174.6 (3)C30—C31—C32—C36175.4 (3)
C9—C10—C11—C120.0C31—C32—C33—C34−0.2
C14—C10—C11—C12174.4 (3)C36—C32—C33—C34−176.4 (2)
C10—C11—C12—C130.0C32—C33—C34—C350.5
C11—C12—C13—C80.0O4—C30—C35—C34172.55 (16)
O2—C8—C13—C12−172.2 (3)C31—C30—C35—C34−1.3
C9—C8—C13—C120.0C33—C34—C35—C300.3
C9—C10—C14—C15−176.6 (3)C33—C32—C36—C37177.4 (3)
C11—C10—C14—C158.9 (4)C31—C32—C36—C371.5 (4)
C9—C10—C14—C1962.5 (4)C33—C32—C36—C4154.6 (4)
C11—C10—C14—C19−112.0 (3)C31—C32—C36—C41−121.4 (3)
C9—C10—C14—C20−55.4 (4)C33—C32—C36—C42−61.4 (4)
C11—C10—C14—C20130.1 (3)C31—C32—C36—C42122.7 (3)
C19—C14—C15—C1638.0 (5)C32—C36—C37—C38−78.6 (5)
C20—C14—C15—C16157.2 (4)C41—C36—C37—C3840.5 (5)
C10—C14—C15—C16−80.3 (5)C42—C36—C37—C38159.3 (4)
C14—C15—C16—C17−87.6 (5)C36—C37—C38—C39−87.5 (5)
C15—C16—C17—C1869.6 (6)C37—C38—C39—C4068.5 (8)
C19—N2—C18—C1772.7 (6)C41—N4—C40—C3975.8 (6)
C22—N2—C18—C17−165.2 (4)C44—N4—C40—C39−164.4 (5)
C16—C17—C18—N2−52.7 (7)C38—C39—C40—N4−52.7 (8)
C22—N2—C19—C14143.9 (4)C40—N4—C41—C36−95.9 (6)
C18—N2—C19—C14−94.0 (5)C44—N4—C41—C36143.6 (5)
C15—C14—C19—N244.3 (5)C37—C36—C41—N441.0 (5)
C20—C14—C19—N2−74.6 (5)C32—C36—C41—N4164.6 (4)
C10—C14—C19—N2166.4 (4)C42—C36—C41—N4−78.1 (5)
C15—C14—C20—C2161.0 (5)C37—C36—C42—C4355.2 (5)
C19—C14—C20—C21−178.7 (4)C32—C36—C42—C43−68.9 (5)
C10—C14—C20—C21−62.5 (5)C41—C36—C42—C43176.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.862.153.007 (5)177
N1—H1···O1ii0.862.163.002 (5)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2204).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ennis, C., Haroun, F. & Lattimer, N. J. (1986). Pharm. Pharmacol.38, 24–27. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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