2-Methoxy-4-methyl-6,7,8,9-tetra­hydro-5H-cyclo­hepta­[b]­pyridine

The title compound, C₁₂H₁₇NO, was synthesized and characterized by ¹H NMR and X-ray diffraction techniques.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.067
• wR factor = 0.165
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Author Response: Not collected reflections were marked as collisions.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Methoxy-4-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

Crystal data

C12H17NO	F(000) = 416
Mr = 191.27	Dx = 1.207 Mg m^−3
Monoclinic, P21/c	Melting point = 310–314 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.762 (2) Å	Cell parameters from 450 reflections
b = 14.937 (4) Å	θ = 3–26°
c = 8.542 (7) Å	µ = 0.08 mm^−1
β = 109.659 (6)°	T = 120 K
V = 1052.8 (9) Å^3	Needle, colourless
Z = 4	0.3 × 0.1 × 0.1 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2498 independent reflections
Radiation source: fine-focus sealed tube	1435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.007
φ and ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→11
Tmin = 0.991, Tmax = 0.992	k = −19→19
7211 measured reflections	l = −9→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.1049P)^2] where P = (Fo^2 + 2Fc^2)/3
2498 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. ¹H NMR spectrum was recorded on a Bruker AMX–400. Atoms are numbered according to Fig. 1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.77900 (19)	0.02285 (10)	0.7016 (2)	0.0269 (4)
O2	0.76371 (17)	0.16165 (9)	0.81532 (17)	0.0329 (4)
C2	0.7314 (2)	0.10754 (12)	0.6801 (2)	0.0257 (4)
C3	0.6513 (2)	0.14523 (12)	0.5264 (2)	0.0274 (5)
H3	0.6216	0.2067	0.5178	0.033*
C4	0.6150 (2)	0.09263 (12)	0.3856 (2)	0.0271 (5)
C5	0.6655 (2)	0.00229 (12)	0.4049 (2)	0.0255 (4)
C6	0.6358 (2)	−0.05941 (13)	0.2573 (3)	0.0318 (5)
H6A	0.5670	−0.0278	0.1564	0.038*
H6B	0.5745	−0.1122	0.2735	0.038*
C7	0.7913 (2)	−0.09229 (14)	0.2273 (3)	0.0336 (5)
H7A	0.7622	−0.1124	0.1105	0.040*
H7B	0.8671	−0.0413	0.2430	0.040*
C8	0.8777 (3)	−0.16833 (13)	0.3409 (3)	0.0331 (5)
H8A	0.8023	−0.2197	0.3225	0.040*
H8B	0.9706	−0.1875	0.3078	0.040*
C9	0.9398 (2)	−0.14704 (13)	0.5248 (3)	0.0323 (5)
H9A	1.0162	−0.0961	0.5440	0.039*
H9B	1.0009	−0.1994	0.5856	0.039*
C10	0.8064 (2)	−0.12340 (12)	0.5974 (2)	0.0300 (5)
H10A	0.7142	−0.1650	0.5506	0.036*
H10B	0.8492	−0.1329	0.7192	0.036*
C11	0.7453 (2)	−0.02922 (11)	0.5638 (2)	0.0251 (4)
C12	0.5230 (3)	0.13253 (14)	0.2201 (3)	0.0353 (5)
H12A	0.5066	0.1966	0.2334	0.053*
H12B	0.4176	0.1028	0.1742	0.053*
H12C	0.5846	0.1243	0.1443	0.053*
C13	0.8495 (3)	0.12171 (15)	0.9723 (3)	0.0382 (5)
H13A	0.7868	0.0712	0.9918	0.057*
H13B	0.8653	0.1662	1.0607	0.057*
H13C	0.9551	0.1003	0.9721	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0252 (9)	0.0303 (8)	0.0253 (9)	−0.0008 (6)	0.0085 (7)	−0.0002 (7)
O2	0.0369 (9)	0.0329 (7)	0.0268 (8)	0.0000 (6)	0.0078 (7)	−0.0059 (6)
C2	0.0237 (10)	0.0308 (9)	0.0235 (11)	−0.0033 (7)	0.0091 (8)	−0.0046 (8)
C3	0.0265 (11)	0.0273 (9)	0.0296 (12)	0.0007 (7)	0.0108 (9)	0.0004 (8)
C4	0.0258 (10)	0.0333 (10)	0.0232 (11)	−0.0010 (8)	0.0094 (9)	0.0012 (8)
C5	0.0209 (10)	0.0331 (9)	0.0231 (11)	−0.0011 (8)	0.0081 (8)	−0.0003 (8)
C6	0.0302 (12)	0.0373 (10)	0.0237 (11)	0.0003 (8)	0.0036 (9)	−0.0033 (8)
C7	0.0320 (12)	0.0436 (11)	0.0248 (12)	−0.0040 (9)	0.0092 (10)	−0.0064 (9)
C8	0.0344 (12)	0.0334 (10)	0.0354 (13)	−0.0023 (8)	0.0168 (10)	−0.0072 (9)
C9	0.0320 (11)	0.0291 (9)	0.0337 (12)	0.0016 (8)	0.0084 (10)	−0.0006 (8)
C10	0.0356 (12)	0.0272 (9)	0.0256 (11)	−0.0007 (8)	0.0083 (9)	0.0013 (8)
C11	0.0250 (10)	0.0277 (9)	0.0232 (11)	−0.0007 (8)	0.0088 (9)	−0.0002 (8)
C12	0.0388 (12)	0.0377 (11)	0.0303 (12)	0.0048 (9)	0.0128 (10)	0.0040 (9)
C13	0.0409 (13)	0.0453 (12)	0.0248 (12)	−0.0012 (10)	0.0064 (10)	−0.0061 (9)

Geometric parameters (Å, º)

N1—C2	1.325 (2)	C7—H7B	0.9900
N1—C11	1.358 (2)	C8—C9	1.513 (3)
O2—C2	1.359 (2)	C8—H8A	0.9900
O2—C13	1.428 (3)	C8—H8B	0.9900
C2—C3	1.383 (3)	C9—C10	1.537 (3)
C3—C4	1.381 (3)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.412 (3)	C10—C11	1.498 (2)
C4—C12	1.495 (3)	C10—H10A	0.9900
C5—C11	1.383 (3)	C10—H10B	0.9900
C5—C6	1.512 (3)	C12—H12A	0.9800
C6—C7	1.548 (3)	C12—H12B	0.9800
C6—H6A	0.9900	C12—H12C	0.9800
C6—H6B	0.9900	C13—H13A	0.9800
C7—C8	1.520 (3)	C13—H13B	0.9800
C7—H7A	0.9900	C13—H13C	0.9800
C2—N1—C11	117.40 (16)	C7—C8—H8B	108.4
C2—O2—C13	116.29 (16)	H8A—C8—H8B	107.4
N1—C2—O2	118.95 (17)	C8—C9—C10	114.26 (17)
N1—C2—C3	123.75 (17)	C8—C9—H9A	108.7
O2—C2—C3	117.31 (17)	C10—C9—H9A	108.7
C4—C3—C2	119.32 (17)	C8—C9—H9B	108.7
C4—C3—H3	120.3	C10—C9—H9B	108.7
C2—C3—H3	120.3	H9A—C9—H9B	107.6
C3—C4—C5	118.05 (17)	C11—C10—C9	114.20 (16)
C3—C4—C12	119.29 (18)	C11—C10—H10A	108.7
C5—C4—C12	122.65 (17)	C9—C10—H10A	108.7
C11—C5—C4	118.35 (17)	C11—C10—H10B	108.7
C11—C5—C6	119.94 (17)	C9—C10—H10B	108.7
C4—C5—C6	121.70 (17)	H10A—C10—H10B	107.6
C5—C6—C7	114.66 (16)	N1—C11—C5	123.11 (17)
C5—C6—H6A	108.6	N1—C11—C10	114.34 (16)
C7—C6—H6A	108.6	C5—C11—C10	122.52 (17)
C5—C6—H6B	108.6	C4—C12—H12A	109.5
C7—C6—H6B	108.6	C4—C12—H12B	109.5
H6A—C6—H6B	107.6	H12A—C12—H12B	109.5
C8—C7—C6	114.11 (17)	C4—C12—H12C	109.5
C8—C7—H7A	108.7	H12A—C12—H12C	109.5
C6—C7—H7A	108.7	H12B—C12—H12C	109.5
C8—C7—H7B	108.7	O2—C13—H13A	109.5
C6—C7—H7B	108.7	O2—C13—H13B	109.5
H7A—C7—H7B	107.6	H13A—C13—H13B	109.5
C9—C8—C7	115.69 (17)	O2—C13—H13C	109.5
C9—C8—H8A	108.4	H13A—C13—H13C	109.5
C7—C8—H8A	108.4	H13B—C13—H13C	109.5
C9—C8—H8B	108.4