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The title compound, 4-meth­oxy-12-meth­yl-12-aza­tetra­cyclo­[9.31,10.02,7]hepta­deca-2(7),3,5-triene, C18H25NO, has a T-shaped configuration, with the benzene ring (A) and the fused carbocyclic ring (C) forming the upright stock; the other carbocyclic ring (D) and the piperidine ring (E) are in the arm positions. Rings C, D and E have sofa, chair and chair conformations, respectively. In the crystal packing, the mol­ecules are joined through C—H...O hydrogen bonding into chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017782/is6088sup1.cif
Contains datablocks pu22, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017782/is6088Isup2.hkl
Contains datablock I

CCDC reference: 277705

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.102
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.99 From the CIF: _reflns_number_total 2066 Count of symmetry unique reflns 2097 Completeness (_total/calc) 98.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4-methoxy-12-methyl-12-azatetracyclo[9.31.10.02.7] heptadeca-2(7),3,5-triene top
Crystal data top
C18H25NOF(000) = 592
Mr = 271.39Dx = 1.195 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6946 reflections
a = 14.0356 (12) Åθ = 2.7–27.8°
b = 15.0658 (13) ŵ = 0.07 mm1
c = 7.1354 (6) ÅT = 273 K
V = 1508.8 (2) Å3Needle, colourless
Z = 40.22 × 0.18 × 0.16 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
ω scansh = 1818
13046 measured reflectionsk = 1919
2066 independent reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.1352P]
where P = (Fo2 + 2Fc2)/3
2066 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

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) top
xyzUiso*/Ueq
C11.13876 (11)0.25661 (11)0.7611 (2)0.0413 (4)
H11.15310.31670.75080.050*
C21.19995 (12)0.19619 (12)0.6849 (2)0.0443 (4)
H21.25490.21490.62360.053*
C31.17914 (11)0.10603 (12)0.7000 (2)0.0406 (4)
C41.09516 (11)0.07922 (10)0.7868 (2)0.0377 (3)
H41.08040.01910.79300.045*
C50.89891 (12)0.02597 (11)0.8931 (3)0.0433 (4)
H5A0.94700.01980.87950.052*
H5B0.85100.00430.97970.052*
C60.85252 (14)0.04260 (13)0.7034 (3)0.0547 (5)
H6A0.90110.05900.61310.066*
H6B0.82240.01160.66000.066*
C70.77850 (14)0.11596 (14)0.7154 (3)0.0593 (5)
H7A0.72630.09690.79490.071*
H7B0.75310.12780.59140.071*
C80.82238 (13)0.20085 (12)0.7951 (3)0.0483 (4)
H8A0.86930.22370.70770.058*
H8B0.77300.24540.80970.058*
C90.91478 (11)0.26648 (11)1.0712 (2)0.0384 (3)
H90.86500.31201.07830.046*
C100.99298 (12)0.30212 (10)0.9411 (2)0.0410 (3)
H10A0.96320.33600.84150.049*
H10B1.03310.34241.01180.049*
C111.05504 (10)0.23151 (10)0.8543 (2)0.0356 (3)
C121.03261 (10)0.14125 (10)0.8649 (2)0.0342 (3)
C130.94546 (10)0.10962 (10)0.9759 (2)0.0347 (3)
C140.86987 (10)0.18396 (10)0.9845 (2)0.0374 (3)
H140.81990.16391.07060.045*
C150.97785 (12)0.09145 (11)1.1794 (2)0.0419 (4)
H15A0.92470.06751.24990.050*
H15B1.02800.04711.17820.050*
C161.01421 (12)0.17438 (12)1.2771 (2)0.0447 (4)
H16A1.02680.16121.40780.054*
H16B1.07350.19311.21970.054*
C170.97607 (15)0.32453 (13)1.3656 (3)0.0557 (5)
H17A1.03550.34471.31420.083*
H17B0.98460.30991.49550.083*
H17C0.92930.37071.35420.083*
C181.22770 (17)0.04348 (14)0.6454 (4)0.0662 (6)
H18A1.17220.05810.57310.099*
H18B1.21690.05860.77440.099*
H18C1.28140.07620.59890.099*
O11.24627 (9)0.04877 (10)0.6304 (2)0.0565 (4)
N10.94412 (10)0.24632 (9)1.2641 (2)0.0423 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0389 (7)0.0397 (8)0.0452 (8)0.0099 (6)0.0021 (7)0.0055 (7)
C20.0330 (7)0.0566 (9)0.0432 (8)0.0091 (7)0.0036 (7)0.0043 (8)
C30.0339 (7)0.0496 (8)0.0384 (8)0.0030 (6)0.0025 (6)0.0032 (7)
C40.0354 (7)0.0381 (7)0.0394 (8)0.0041 (6)0.0006 (6)0.0011 (6)
C50.0385 (7)0.0369 (8)0.0545 (10)0.0073 (6)0.0045 (7)0.0033 (7)
C60.0552 (10)0.0491 (9)0.0599 (11)0.0131 (8)0.0099 (9)0.0073 (9)
C70.0521 (9)0.0603 (11)0.0655 (12)0.0104 (9)0.0200 (10)0.0016 (10)
C80.0433 (8)0.0466 (9)0.0551 (10)0.0007 (7)0.0133 (8)0.0046 (8)
C90.0379 (7)0.0376 (7)0.0397 (7)0.0049 (6)0.0004 (7)0.0018 (6)
C100.0459 (8)0.0345 (7)0.0425 (8)0.0017 (6)0.0033 (7)0.0029 (6)
C110.0349 (7)0.0374 (7)0.0345 (7)0.0031 (6)0.0021 (6)0.0036 (6)
C120.0316 (6)0.0384 (7)0.0325 (7)0.0037 (6)0.0013 (6)0.0027 (6)
C130.0319 (6)0.0356 (7)0.0367 (7)0.0021 (6)0.0027 (6)0.0049 (6)
C140.0316 (6)0.0402 (8)0.0404 (7)0.0004 (6)0.0019 (6)0.0043 (7)
C150.0426 (8)0.0431 (8)0.0402 (8)0.0037 (7)0.0030 (7)0.0105 (7)
C160.0450 (8)0.0523 (9)0.0370 (8)0.0039 (7)0.0045 (7)0.0054 (7)
C170.0617 (11)0.0564 (11)0.0489 (9)0.0015 (9)0.0027 (9)0.0098 (9)
C180.0637 (11)0.0522 (11)0.0827 (15)0.0017 (9)0.0251 (12)0.0183 (11)
O10.0439 (6)0.0561 (8)0.0696 (9)0.0027 (6)0.0182 (7)0.0100 (7)
N10.0450 (7)0.0445 (7)0.0372 (7)0.0026 (6)0.0009 (6)0.0014 (6)
Geometric parameters (Å, º) top
C1—C21.365 (2)C9—C101.535 (2)
C1—C111.402 (2)C9—H90.9800
C1—H10.9300C10—C111.508 (2)
C2—C31.394 (3)C10—H10A0.9700
C2—H20.9300C10—H10B0.9700
C3—O11.371 (2)C11—C121.398 (2)
C3—C41.392 (2)C12—C131.533 (2)
C4—C121.398 (2)C13—C141.544 (2)
C4—H40.9300C13—C151.546 (2)
C5—C61.522 (3)C14—H140.9800
C5—C131.538 (2)C15—C161.519 (2)
C5—H5A0.9700C15—H15A0.9700
C5—H5B0.9700C15—H15B0.9700
C6—C71.519 (3)C16—N11.467 (2)
C6—H6A0.9700C16—H16A0.9700
C6—H6B0.9700C16—H16B0.9700
C7—C81.529 (3)C17—N11.454 (2)
C7—H7A0.9700C17—H17A0.9600
C7—H7B0.9700C17—H17B0.9600
C8—C141.529 (2)C17—H17C0.9600
C8—H8A0.9700C18—O11.418 (2)
C8—H8B0.9700C18—H18A0.9600
C9—N11.468 (2)C18—H18B0.9600
C9—C141.525 (2)C18—H18C0.9600
C2—C1—C11122.45 (15)H10A—C10—H10B107.6
C2—C1—H1118.8C12—C11—C1118.46 (15)
C11—C1—H1118.8C12—C11—C10122.29 (14)
C1—C2—C3119.18 (15)C1—C11—C10119.25 (14)
C1—C2—H2120.4C11—C12—C4119.17 (14)
C3—C2—H2120.4C11—C12—C13120.66 (14)
O1—C3—C4124.12 (15)C4—C12—C13119.94 (14)
O1—C3—C2116.19 (14)C12—C13—C5113.29 (13)
C4—C3—C2119.66 (15)C12—C13—C14110.08 (12)
C3—C4—C12121.02 (14)C5—C13—C14108.54 (12)
C3—C4—H4119.5C12—C13—C15107.79 (12)
C12—C4—H4119.5C5—C13—C15109.93 (13)
C6—C5—C13112.86 (14)C14—C13—C15107.03 (13)
C6—C5—H5A109.0C9—C14—C8113.78 (13)
C13—C5—H5A109.0C9—C14—C13108.88 (12)
C6—C5—H5B109.0C8—C14—C13112.64 (13)
C13—C5—H5B109.0C9—C14—H14107.1
H5A—C5—H5B107.8C8—C14—H14107.1
C7—C6—C5111.24 (17)C13—C14—H14107.1
C7—C6—H6A109.4C16—C15—C13112.60 (13)
C5—C6—H6A109.4C16—C15—H15A109.1
C7—C6—H6B109.4C13—C15—H15A109.1
C5—C6—H6B109.4C16—C15—H15B109.1
H6A—C6—H6B108.0C13—C15—H15B109.1
C6—C7—C8110.72 (14)H15A—C15—H15B107.8
C6—C7—H7A109.5N1—C16—C15110.70 (13)
C8—C7—H7A109.5N1—C16—H16A109.5
C6—C7—H7B109.5C15—C16—H16A109.5
C8—C7—H7B109.5N1—C16—H16B109.5
H7A—C7—H7B108.1C15—C16—H16B109.5
C14—C8—C7111.43 (15)H16A—C16—H16B108.1
C14—C8—H8A109.3N1—C17—H17A109.5
C7—C8—H8A109.3N1—C17—H17B109.5
C14—C8—H8B109.3H17A—C17—H17B109.5
C7—C8—H8B109.3N1—C17—H17C109.5
H8A—C8—H8B108.0H17A—C17—H17C109.5
N1—C9—C14109.12 (13)H17B—C17—H17C109.5
N1—C9—C10116.03 (13)O1—C18—H18A109.5
C14—C9—C10109.60 (13)O1—C18—H18B109.5
N1—C9—H9107.2H18A—C18—H18B109.5
C14—C9—H9107.2O1—C18—H18C109.5
C10—C9—H9107.2H18A—C18—H18C109.5
C11—C10—C9114.50 (13)H18B—C18—H18C109.5
C11—C10—H10A108.6C3—O1—C18117.59 (14)
C9—C10—H10A108.6C17—N1—C16111.13 (14)
C11—C10—H10B108.6C17—N1—C9112.70 (14)
C9—C10—H10B108.6C16—N1—C9113.60 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18B···O1i0.962.603.480 (3)153
Symmetry code: (i) x+5/2, y, z+1/2.
 

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