Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031285/tk2171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031285/tk2171Isup2.hkl |
CCDC reference: 657676
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.012 Å
- R factor = 0.129
- wR factor = 0.289
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.159 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.129 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.289 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT082_ALERT_2_C High R1 Value .................................. 0.13 PLAT084_ALERT_2_C High R2 Value .................................. 0.29 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT414_ALERT_2_C Short Intra D-H..H-X H2 .. H9A .. 1.91 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of pentafluorophenol (0.130 g, 0.706 mmol) in dichloromethane (5 ml), 3-ethylindole-2-carboxylic acid (0.100 g, 0.447 mmol) (Muirhead & Trembleau, 2007) and N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.111 g, 0.581 mmol) were added and stirred at room temperature for 80 min. Silica gel (1.2 g) was added to the reaction mixture, stirred for 5 min and the mixture filtered through Celite and the solvent removed to give the activated ester as a white solid (0.167 g). The ester was redissolved in dichloromethane (2.6 ml), to which was added 2-morpholinoethylamine 5 (0.068 ml, 0.514 mmol) and triethylamine (0.072 ml, 0.514 mmol) and stirred at room temperature for 80 min. The solvent was removed under vacuum and the resulting solid taken up into ethyl acetate (30 ml), washed with saturated potassium carbonate solution (5 ml), dried over magnesium sulfate, filtered and dried. Recrystallization of the crude material from hot ethanol afforded 0.066 g (44%) of colourless blocks of (I)
The H atoms were placed in idealized locations (C—H = 0.93–0.99 Å, N—H = 0.88 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).
As part of our on-going investigations of allosteric modulators of the cannabinoid CB1 receptor (Price et al., 2005), the title compound, (I), C17H22ClN3O2, has been synthesized and structurally characterized (Fig. 1). It complements C18H24ClN3O2, reported in the next paper (Muirhead, Trembleau & Harrison, 2007).
The dihedral angle between the mean planes of the C1—C8/N1 fused aromatic ring system and atoms C6/C7/N1/O2 in (I) is 14.66 (16)°, i.e. the two fragments are slightly twisted. Atom C10 is displaced from the C1—C8/N1 mean plane by 1.459 (14) Å. The C14—C17/N3/O2 ring in (I) has a typical chair conformation, with N3 and O2 displaced from the mean plane of the carbon atoms by -0.656 (12)Å and 0.635 (14) Å, respectively. Otherwise, the bond lengths and angles in (I) may be regarded as normal (Allen et al., 1995).
The crystal packing for (I) results in inversion dimers linked by N1—H1···O1i hydrogen bonds (Table 1), thus forming R22(10) loops (Bernstein et al., 1995). The amide N2—H2 group is sterically blocked by the C9/C10 ethyl substituent to the 5-membered ring from making an hydrogen bond. A short C—H···O interaction also occurs (Table 1).
For a related structure, see: Muirhead et al. (2007). For background, see: Price et al. (2005); Allen et al. (1995); Bernstein et al. (1995). For related literature, see: Muirhead & Trembleau (2007).
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C17H22ClN3O2 | Z = 2 |
Mr = 335.83 | F(000) = 356 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1886 (13) Å | Cell parameters from 3029 reflections |
b = 9.7175 (13) Å | θ = 2.9–27.5° |
c = 11.2807 (10) Å | µ = 0.24 mm−1 |
α = 73.755 (6)° | T = 120 K |
β = 79.612 (6)° | Block, colourles |
γ = 63.056 (5)° | 0.12 × 0.08 × 0.06 mm |
V = 860.38 (18) Å3 |
Nonius KappaCCD diffractometer | 3155 independent reflections |
Radiation source: fine-focus sealed tube | 1516 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.159 |
ω and φ scans | θmax = 25.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −11→11 |
Tmin = 0.972, Tmax = 0.987 | k = −11→11 |
10924 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.129 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.289 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.039P)2 + 4.7894P] where P = (Fo2 + 2Fc2)/3 |
3155 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C17H22ClN3O2 | γ = 63.056 (5)° |
Mr = 335.83 | V = 860.38 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1886 (13) Å | Mo Kα radiation |
b = 9.7175 (13) Å | µ = 0.24 mm−1 |
c = 11.2807 (10) Å | T = 120 K |
α = 73.755 (6)° | 0.12 × 0.08 × 0.06 mm |
β = 79.612 (6)° |
Nonius KappaCCD diffractometer | 3155 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 1516 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.987 | Rint = 0.159 |
10924 measured reflections |
R[F2 > 2σ(F2)] = 0.129 | 0 restraints |
wR(F2) = 0.289 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.36 e Å−3 |
3155 reflections | Δρmin = −0.38 e Å−3 |
208 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9563 (9) | 0.2441 (9) | 0.5535 (6) | 0.0404 (19) | |
C2 | 1.0584 (10) | 0.1514 (9) | 0.4714 (7) | 0.046 (2) | |
H2A | 1.1222 | 0.0414 | 0.5016 | 0.055* | |
C3 | 1.0679 (9) | 0.2169 (9) | 0.3478 (7) | 0.0393 (18) | |
H3 | 1.1365 | 0.1547 | 0.2908 | 0.047* | |
C4 | 0.9723 (9) | 0.3796 (8) | 0.3089 (6) | 0.0353 (18) | |
C5 | 0.8706 (9) | 0.4732 (9) | 0.3911 (7) | 0.0356 (17) | |
C6 | 0.8631 (9) | 0.4013 (9) | 0.5165 (6) | 0.0399 (19) | |
H6 | 0.7941 | 0.4616 | 0.5746 | 0.048* | |
C7 | 0.8504 (9) | 0.6271 (8) | 0.1992 (6) | 0.0364 (18) | |
C8 | 0.7926 (9) | 0.6324 (8) | 0.3215 (6) | 0.0368 (18) | |
C9 | 0.6664 (10) | 0.7674 (9) | 0.3750 (7) | 0.050 (2) | |
H9A | 0.6860 | 0.8630 | 0.3371 | 0.060* | |
H9B | 0.6793 | 0.7417 | 0.4649 | 0.060* | |
C10 | 0.4926 (12) | 0.8046 (14) | 0.3552 (10) | 0.089 (4) | |
H10A | 0.4163 | 0.8933 | 0.3925 | 0.134* | |
H10B | 0.4713 | 0.7113 | 0.3939 | 0.134* | |
H10C | 0.4777 | 0.8334 | 0.2663 | 0.134* | |
C11 | 0.8181 (9) | 0.7478 (9) | 0.0822 (7) | 0.0399 (19) | |
C12 | 0.7132 (13) | 1.0292 (9) | −0.0191 (7) | 0.061 (3) | |
H12A | 0.5991 | 1.0711 | −0.0417 | 0.073* | |
H12B | 0.7875 | 0.9927 | −0.0903 | 0.073* | |
C13 | 0.7398 (12) | 1.1575 (10) | 0.0105 (7) | 0.057 (2) | |
H13A | 0.8584 | 1.1229 | 0.0143 | 0.069* | |
H13B | 0.6993 | 1.2542 | −0.0565 | 0.069* | |
C14 | 0.4797 (11) | 1.2850 (12) | 0.1173 (8) | 0.063 (3) | |
H14A | 0.4356 | 1.2223 | 0.0920 | 0.075* | |
H14B | 0.4569 | 1.3843 | 0.0530 | 0.075* | |
C15 | 0.3973 (12) | 1.3236 (14) | 0.2387 (10) | 0.086 (4) | |
H15A | 0.2785 | 1.3875 | 0.2289 | 0.103* | |
H15B | 0.4121 | 1.2238 | 0.3004 | 0.103* | |
C16 | 0.6288 (13) | 1.3189 (14) | 0.2949 (10) | 0.080 (3) | |
H16A | 0.6501 | 1.2182 | 0.3571 | 0.096* | |
H16B | 0.6721 | 1.3793 | 0.3243 | 0.096* | |
C17 | 0.7163 (10) | 1.2833 (11) | 0.1741 (8) | 0.060 (2) | |
H17A | 0.7002 | 1.3838 | 0.1129 | 0.072* | |
H17B | 0.8350 | 1.2211 | 0.1851 | 0.072* | |
N1 | 0.9593 (7) | 0.4741 (7) | 0.1933 (5) | 0.0373 (15) | |
H1 | 1.0119 | 0.4427 | 0.1256 | 0.045* | |
N2 | 0.7448 (9) | 0.8985 (7) | 0.0874 (5) | 0.053 (2) | |
H2 | 0.7130 | 0.9207 | 0.1609 | 0.064* | |
N3 | 0.6561 (8) | 1.1948 (7) | 0.1276 (6) | 0.0426 (16) | |
O1 | 0.8611 (7) | 0.7085 (6) | −0.0193 (5) | 0.0570 (16) | |
O2 | 0.4578 (8) | 1.4077 (9) | 0.2841 (7) | 0.086 (2) | |
Cl1 | 0.9493 (3) | 0.1505 (3) | 0.71052 (19) | 0.0626 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.038 (5) | 0.045 (5) | 0.034 (4) | −0.022 (4) | −0.005 (4) | 0.005 (4) |
C2 | 0.039 (5) | 0.039 (5) | 0.047 (5) | −0.008 (4) | −0.003 (4) | −0.006 (4) |
C3 | 0.034 (4) | 0.042 (5) | 0.039 (4) | −0.014 (4) | 0.001 (3) | −0.013 (4) |
C4 | 0.031 (4) | 0.036 (4) | 0.041 (4) | −0.018 (4) | 0.003 (3) | −0.009 (4) |
C5 | 0.031 (4) | 0.038 (4) | 0.043 (4) | −0.017 (4) | 0.000 (4) | −0.015 (4) |
C6 | 0.041 (5) | 0.046 (5) | 0.031 (4) | −0.020 (4) | 0.008 (3) | −0.011 (4) |
C7 | 0.040 (5) | 0.033 (4) | 0.035 (4) | −0.014 (4) | −0.004 (3) | −0.007 (3) |
C8 | 0.037 (4) | 0.035 (4) | 0.040 (4) | −0.014 (4) | 0.004 (4) | −0.017 (4) |
C9 | 0.061 (6) | 0.044 (5) | 0.037 (4) | −0.019 (4) | 0.002 (4) | −0.008 (4) |
C10 | 0.052 (7) | 0.104 (9) | 0.083 (8) | −0.007 (6) | 0.008 (6) | −0.033 (7) |
C11 | 0.042 (5) | 0.037 (5) | 0.039 (4) | −0.014 (4) | −0.003 (4) | −0.010 (4) |
C12 | 0.103 (8) | 0.037 (5) | 0.034 (4) | −0.025 (5) | −0.003 (5) | −0.003 (4) |
C13 | 0.072 (7) | 0.042 (5) | 0.047 (5) | −0.019 (5) | 0.008 (5) | −0.008 (4) |
C14 | 0.063 (7) | 0.074 (7) | 0.063 (6) | −0.040 (6) | −0.001 (5) | −0.017 (5) |
C15 | 0.047 (6) | 0.115 (9) | 0.112 (9) | −0.034 (6) | 0.018 (6) | −0.066 (8) |
C16 | 0.070 (8) | 0.105 (9) | 0.099 (8) | −0.044 (7) | 0.005 (6) | −0.069 (7) |
C17 | 0.040 (5) | 0.059 (6) | 0.077 (6) | −0.012 (5) | −0.001 (5) | −0.029 (5) |
N1 | 0.044 (4) | 0.035 (4) | 0.029 (3) | −0.012 (3) | 0.003 (3) | −0.014 (3) |
N2 | 0.089 (6) | 0.032 (4) | 0.026 (3) | −0.015 (4) | 0.000 (3) | −0.009 (3) |
N3 | 0.038 (4) | 0.045 (4) | 0.048 (4) | −0.015 (3) | 0.000 (3) | −0.021 (3) |
O1 | 0.071 (4) | 0.048 (3) | 0.035 (3) | −0.008 (3) | −0.001 (3) | −0.018 (3) |
O2 | 0.049 (4) | 0.105 (6) | 0.129 (6) | −0.031 (4) | 0.018 (4) | −0.080 (5) |
Cl1 | 0.0756 (17) | 0.0625 (15) | 0.0402 (12) | −0.0305 (13) | −0.0032 (11) | 0.0040 (10) |
C1—C6 | 1.352 (10) | C12—N2 | 1.442 (9) |
C1—C2 | 1.393 (10) | C12—C13 | 1.505 (11) |
C1—Cl1 | 1.754 (7) | C12—H12A | 0.9900 |
C2—C3 | 1.366 (10) | C12—H12B | 0.9900 |
C2—H2A | 0.9500 | C13—N3 | 1.455 (9) |
C3—C4 | 1.399 (10) | C13—H13A | 0.9900 |
C3—H3 | 0.9500 | C13—H13B | 0.9900 |
C4—N1 | 1.357 (9) | C14—N3 | 1.460 (11) |
C4—C5 | 1.397 (9) | C14—C15 | 1.499 (12) |
C5—C6 | 1.397 (10) | C14—H14A | 0.9900 |
C5—C8 | 1.429 (10) | C14—H14B | 0.9900 |
C6—H6 | 0.9500 | C15—O2 | 1.410 (11) |
C7—N1 | 1.378 (9) | C15—H15A | 0.9900 |
C7—C8 | 1.393 (9) | C15—H15B | 0.9900 |
C7—C11 | 1.472 (10) | C16—O2 | 1.418 (11) |
C8—C9 | 1.497 (10) | C16—C17 | 1.497 (12) |
C9—C10 | 1.514 (12) | C16—H16A | 0.9900 |
C9—H9A | 0.9900 | C16—H16B | 0.9900 |
C9—H9B | 0.9900 | C17—N3 | 1.452 (10) |
C10—H10A | 0.9800 | C17—H17A | 0.9900 |
C10—H10B | 0.9800 | C17—H17B | 0.9900 |
C10—H10C | 0.9800 | N1—H1 | 0.8800 |
C11—O1 | 1.248 (8) | N2—H2 | 0.8800 |
C11—N2 | 1.319 (9) | ||
C6—C1—C2 | 122.5 (7) | C13—C12—H12B | 109.8 |
C6—C1—Cl1 | 119.6 (6) | H12A—C12—H12B | 108.3 |
C2—C1—Cl1 | 117.9 (6) | N3—C13—C12 | 111.9 (7) |
C3—C2—C1 | 120.7 (7) | N3—C13—H13A | 109.2 |
C3—C2—H2A | 119.7 | C12—C13—H13A | 109.2 |
C1—C2—H2A | 119.7 | N3—C13—H13B | 109.2 |
C2—C3—C4 | 117.1 (7) | C12—C13—H13B | 109.2 |
C2—C3—H3 | 121.4 | H13A—C13—H13B | 107.9 |
C4—C3—H3 | 121.4 | N3—C14—C15 | 110.3 (8) |
N1—C4—C5 | 108.2 (6) | N3—C14—H14A | 109.6 |
N1—C4—C3 | 129.4 (7) | C15—C14—H14A | 109.6 |
C5—C4—C3 | 122.3 (7) | N3—C14—H14B | 109.6 |
C4—C5—C6 | 118.7 (7) | C15—C14—H14B | 109.6 |
C4—C5—C8 | 107.9 (6) | H14A—C14—H14B | 108.1 |
C6—C5—C8 | 133.4 (7) | O2—C15—C14 | 113.3 (8) |
C1—C6—C5 | 118.6 (7) | O2—C15—H15A | 108.9 |
C1—C6—H6 | 120.7 | C14—C15—H15A | 108.9 |
C5—C6—H6 | 120.7 | O2—C15—H15B | 108.9 |
N1—C7—C8 | 109.4 (6) | C14—C15—H15B | 108.9 |
N1—C7—C11 | 117.3 (6) | H15A—C15—H15B | 107.7 |
C8—C7—C11 | 133.3 (7) | O2—C16—C17 | 111.7 (8) |
C7—C8—C5 | 105.4 (6) | O2—C16—H16A | 109.3 |
C7—C8—C9 | 130.1 (7) | C17—C16—H16A | 109.3 |
C5—C8—C9 | 124.3 (6) | O2—C16—H16B | 109.3 |
C8—C9—C10 | 113.5 (7) | C17—C16—H16B | 109.3 |
C8—C9—H9A | 108.9 | H16A—C16—H16B | 107.9 |
C10—C9—H9A | 108.9 | N3—C17—C16 | 111.0 (7) |
C8—C9—H9B | 108.9 | N3—C17—H17A | 109.4 |
C10—C9—H9B | 108.9 | C16—C17—H17A | 109.4 |
H9A—C9—H9B | 107.7 | N3—C17—H17B | 109.4 |
C9—C10—H10A | 109.5 | C16—C17—H17B | 109.4 |
C9—C10—H10B | 109.5 | H17A—C17—H17B | 108.0 |
H10A—C10—H10B | 109.5 | C4—N1—C7 | 109.1 (6) |
C9—C10—H10C | 109.5 | C4—N1—H1 | 125.5 |
H10A—C10—H10C | 109.5 | C7—N1—H1 | 125.5 |
H10B—C10—H10C | 109.5 | C11—N2—C12 | 124.4 (6) |
O1—C11—N2 | 120.9 (7) | C11—N2—H2 | 117.8 |
O1—C11—C7 | 120.8 (7) | C12—N2—H2 | 117.8 |
N2—C11—C7 | 118.3 (6) | C17—N3—C13 | 112.2 (6) |
N2—C12—C13 | 109.3 (7) | C17—N3—C14 | 108.7 (6) |
N2—C12—H12A | 109.8 | C13—N3—C14 | 111.6 (7) |
C13—C12—H12A | 109.8 | C15—O2—C16 | 109.2 (7) |
N2—C12—H12B | 109.8 | ||
C6—C1—C2—C3 | −0.3 (12) | N1—C7—C11—O1 | 14.0 (11) |
Cl1—C1—C2—C3 | 179.3 (6) | C8—C7—C11—O1 | −166.0 (8) |
C1—C2—C3—C4 | 0.5 (11) | N1—C7—C11—N2 | −165.1 (7) |
C2—C3—C4—N1 | 179.5 (7) | C8—C7—C11—N2 | 14.9 (13) |
C2—C3—C4—C5 | −0.1 (11) | N2—C12—C13—N3 | −48.9 (10) |
N1—C4—C5—C6 | 179.8 (6) | N3—C14—C15—O2 | 56.9 (12) |
C3—C4—C5—C6 | −0.6 (11) | O2—C16—C17—N3 | −58.9 (11) |
N1—C4—C5—C8 | −0.2 (8) | C5—C4—N1—C7 | −0.3 (8) |
C3—C4—C5—C8 | 179.4 (7) | C3—C4—N1—C7 | −179.8 (7) |
C2—C1—C6—C5 | −0.3 (12) | C8—C7—N1—C4 | 0.6 (8) |
Cl1—C1—C6—C5 | −179.9 (6) | C11—C7—N1—C4 | −179.4 (6) |
C4—C5—C6—C1 | 0.8 (11) | O1—C11—N2—C12 | −2.5 (13) |
C8—C5—C6—C1 | −179.2 (8) | C7—C11—N2—C12 | 176.6 (8) |
N1—C7—C8—C5 | −0.7 (8) | C13—C12—N2—C11 | −141.5 (8) |
C11—C7—C8—C5 | 179.3 (8) | C16—C17—N3—C13 | −179.6 (8) |
N1—C7—C8—C9 | −176.1 (7) | C16—C17—N3—C14 | 56.5 (10) |
C11—C7—C8—C9 | 3.9 (14) | C12—C13—N3—C17 | 163.8 (7) |
C4—C5—C8—C7 | 0.6 (8) | C12—C13—N3—C14 | −74.0 (9) |
C6—C5—C8—C7 | −179.5 (8) | C15—C14—N3—C17 | −54.9 (10) |
C4—C5—C8—C9 | 176.3 (7) | C15—C14—N3—C13 | −179.1 (7) |
C6—C5—C8—C9 | −3.7 (13) | C14—C15—O2—C16 | −56.9 (12) |
C7—C8—C9—C10 | 76.4 (11) | C17—C16—O2—C15 | 57.2 (11) |
C5—C8—C9—C10 | −98.2 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 1.97 | 2.803 (7) | 157 |
C6—H6···O2ii | 0.95 | 2.58 | 3.491 (11) | 161 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H22ClN3O2 |
Mr | 335.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 9.1886 (13), 9.7175 (13), 11.2807 (10) |
α, β, γ (°) | 73.755 (6), 79.612 (6), 63.056 (5) |
V (Å3) | 860.38 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.12 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.972, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10924, 3155, 1516 |
Rint | 0.159 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.129, 0.289, 1.07 |
No. of reflections | 3155 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.38 |
Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 1.97 | 2.803 (7) | 157 |
C6—H6···O2ii | 0.95 | 2.58 | 3.491 (11) | 161 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z+1. |
As part of our on-going investigations of allosteric modulators of the cannabinoid CB1 receptor (Price et al., 2005), the title compound, (I), C17H22ClN3O2, has been synthesized and structurally characterized (Fig. 1). It complements C18H24ClN3O2, reported in the next paper (Muirhead, Trembleau & Harrison, 2007).
The dihedral angle between the mean planes of the C1—C8/N1 fused aromatic ring system and atoms C6/C7/N1/O2 in (I) is 14.66 (16)°, i.e. the two fragments are slightly twisted. Atom C10 is displaced from the C1—C8/N1 mean plane by 1.459 (14) Å. The C14—C17/N3/O2 ring in (I) has a typical chair conformation, with N3 and O2 displaced from the mean plane of the carbon atoms by -0.656 (12)Å and 0.635 (14) Å, respectively. Otherwise, the bond lengths and angles in (I) may be regarded as normal (Allen et al., 1995).
The crystal packing for (I) results in inversion dimers linked by N1—H1···O1i hydrogen bonds (Table 1), thus forming R22(10) loops (Bernstein et al., 1995). The amide N2—H2 group is sterically blocked by the C9/C10 ethyl substituent to the 5-membered ring from making an hydrogen bond. A short C—H···O interaction also occurs (Table 1).