(6R,10R,14E)-6-Amino-12-ethyl­idene-8-methyl-6,7,10,12-tetra­hydro-6,10-methano­cyclo­octa­[b]pyridin-2(1H)-one monohydrate

The crystal structure of the title compound, C₁₅H₁₈N₂O·H₂O, exhibits four independent hydrogen bonds, of types N—H...O and O—H...O. The water mol­ecules participate in extensive hydrogen bonding and link mol­ecules into a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.066
• wR factor = 0.161
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.51
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    1419.00 Ang-3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2A    ..  H3      ..       1.94 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  N2      ..       2.68 Ang.

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           25.00
           From the CIF: _reflns_number_total               1292
           Count of symmetry unique reflns         1314
           Completeness (_total/calc)             98.33%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(6R,10R,14E)-6-Amino-12-ethylidene-8-methyl-6,7,10,12-tetrahydro-6,10- methanocycloocta[b]pyridin-2(1H)-one monohydrate

Crystal data

C15H18N2O·H2O	F(000) = 560
Mr = 260.33	Dx = 1.219 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 682 reflections
a = 14.00 (2) Å	θ = 2.3–20.1°
b = 12.35 (2) Å	µ = 0.08 mm^−1
c = 8.838 (14) Å	T = 298 K
β = 111.731 (19)°	Block, white
V = 1419 (4) Å^3	0.20 × 0.17 × 0.11 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1292 independent reflections
Radiation source: fine-focus sealed tube	751 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 10 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
φ and ω scans	h = −16→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −14→13
Tmin = 0.984, Tmax = 0.991	l = −10→10
3603 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0786P)^2] where P = (Fo^2 + 2Fc^2)/3
1292 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.25 e Å^−3
1 restraint	Δρmin = −0.24 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.8847 (4)	0.3330 (4)	0.8217 (5)	0.0421 (14)
H1	0.9473	0.3537	0.8468	0.051*
N2	0.6021 (4)	0.1441 (5)	0.4456 (6)	0.0591 (18)
H2A	0.5822	0.1478	0.5264	0.071*
H2B	0.5527	0.1330	0.3538	0.071*
O1	0.9042 (3)	0.3612 (4)	1.0844 (5)	0.0550 (13)
O2	0.9567 (4)	0.5875 (5)	0.1216 (7)	0.094 (2)
H16	0.9401	0.5210	0.1163	0.113*
H17	0.9290	0.6109	0.0246	0.113*
C1	0.8459 (4)	0.3315 (5)	0.9425 (7)	0.0457 (18)
C2	0.7446 (4)	0.2966 (6)	0.8981 (7)	0.0474 (18)
H2	0.7143	0.2937	0.9756	0.057*
C3	0.6898 (5)	0.2667 (6)	0.7417 (7)	0.0523 (19)
H3	0.6223	0.2433	0.7142	0.063*
C4	0.7324 (5)	0.2700 (5)	0.6200 (7)	0.0411 (16)
C5	0.8307 (4)	0.3038 (5)	0.6632 (6)	0.0373 (15)
C6	0.6691 (4)	0.2336 (5)	0.4429 (7)	0.0417 (17)
C7	0.6021 (5)	0.3287 (6)	0.3509 (7)	0.0497 (18)
H7A	0.5489	0.3009	0.2533	0.060*
H7B	0.5684	0.3599	0.4189	0.060*
C8	0.6585 (6)	0.4162 (5)	0.3032 (7)	0.0463 (17)
C9	0.7546 (6)	0.4023 (5)	0.3150 (7)	0.0467 (17)
H9	0.7870	0.4595	0.2849	0.056*
C10	0.8144 (4)	0.3007 (5)	0.3736 (6)	0.0419 (16)
H10	0.8546	0.2856	0.3058	0.050*
C11	0.8886 (4)	0.3112 (6)	0.5531 (7)	0.0464 (16)
H11A	0.9396	0.2540	0.5788	0.056*
H11B	0.9242	0.3802	0.5690	0.056*
C12	0.7430 (5)	0.2054 (6)	0.3622 (7)	0.0426 (17)
C13	0.6013 (6)	0.5188 (6)	0.2430 (9)	0.075 (3)
H13A	0.6321	0.5573	0.1782	0.112*
H13B	0.6041	0.5629	0.3341	0.112*
H13C	0.5310	0.5026	0.1780	0.112*
C14	0.7476 (5)	0.1136 (6)	0.2939 (8)	0.0520 (17)
H14	0.6989	0.0624	0.2942	0.062*
C15	0.8197 (7)	0.0789 (7)	0.2155 (11)	0.086 (3)
H15A	0.8561	0.0154	0.2693	0.128*
H15B	0.8678	0.1360	0.2237	0.128*
H15C	0.7817	0.0628	0.1028	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.037 (3)	0.068 (4)	0.023 (2)	−0.008 (3)	0.013 (2)	−0.001 (3)
N2	0.055 (4)	0.092 (5)	0.034 (3)	−0.032 (3)	0.021 (3)	−0.011 (3)
O1	0.050 (3)	0.088 (4)	0.026 (2)	−0.003 (3)	0.0133 (19)	−0.005 (2)
O2	0.096 (4)	0.111 (5)	0.055 (4)	0.001 (4)	0.003 (3)	−0.013 (3)
C1	0.043 (4)	0.066 (5)	0.028 (3)	0.005 (4)	0.014 (3)	0.003 (3)
C2	0.033 (4)	0.084 (5)	0.029 (3)	0.000 (4)	0.017 (3)	−0.004 (4)
C3	0.041 (4)	0.087 (6)	0.033 (3)	−0.014 (4)	0.019 (3)	0.000 (4)
C4	0.043 (4)	0.054 (4)	0.026 (3)	0.002 (3)	0.012 (3)	−0.001 (3)
C5	0.036 (3)	0.056 (4)	0.021 (3)	−0.003 (3)	0.012 (2)	0.000 (3)
C6	0.037 (3)	0.052 (4)	0.034 (4)	−0.002 (3)	0.011 (3)	−0.001 (3)
C7	0.044 (4)	0.072 (5)	0.031 (3)	0.007 (4)	0.011 (3)	0.001 (3)
C8	0.053 (5)	0.052 (4)	0.025 (3)	0.005 (4)	0.004 (3)	−0.001 (3)
C9	0.065 (5)	0.050 (4)	0.020 (3)	−0.003 (4)	0.010 (3)	0.000 (3)
C10	0.046 (3)	0.063 (4)	0.018 (3)	−0.001 (4)	0.013 (2)	0.002 (3)
C11	0.046 (4)	0.059 (4)	0.030 (3)	−0.004 (4)	0.010 (3)	−0.006 (3)
C12	0.042 (4)	0.054 (4)	0.023 (3)	−0.003 (3)	0.002 (3)	0.003 (3)
C13	0.078 (6)	0.076 (6)	0.054 (5)	0.007 (5)	0.007 (5)	−0.002 (4)
C14	0.051 (4)	0.065 (5)	0.044 (4)	−0.010 (4)	0.021 (3)	−0.011 (4)
C15	0.084 (6)	0.089 (7)	0.092 (6)	0.019 (6)	0.042 (5)	−0.015 (6)

Geometric parameters (Å, º)

N1—C1	1.365 (7)	C7—H7A	0.9700
N1—C5	1.371 (7)	C7—H7B	0.9700
N1—H1	0.8600	C8—C9	1.321 (9)
N2—C6	1.455 (8)	C8—C13	1.488 (10)
N2—H2A	0.8598	C9—C10	1.490 (9)
N2—H2B	0.8601	C9—H9	0.9300
O1—C1	1.271 (7)	C10—C12	1.523 (9)
O2—H16	0.8504	C10—C11	1.547 (7)
O2—H17	0.8500	C10—H10	0.9800
C1—C2	1.393 (8)	C11—H11A	0.9700
C2—C3	1.360 (8)	C11—H11B	0.9700
C2—H2	0.9300	C12—C14	1.297 (9)
C3—C4	1.410 (9)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.351 (8)	C13—H13C	0.9600
C4—C6	1.553 (8)	C14—C15	1.483 (10)
C5—C11	1.482 (8)	C14—H14	0.9300
C6—C12	1.498 (9)	C15—H15A	0.9600
C6—C7	1.535 (9)	C15—H15B	0.9600
C7—C8	1.488 (10)	C15—H15C	0.9600
C1—N1—C5	124.6 (5)	C9—C8—C7	120.9 (6)
C1—N1—H1	117.7	C13—C8—C7	116.6 (7)
C5—N1—H1	117.7	C8—C9—C10	124.2 (6)
C6—N2—H2A	112.5	C8—C9—H9	117.9
C6—N2—H2B	113.9	C10—C9—H9	117.9
H2A—N2—H2B	113.3	C9—C10—C12	110.9 (5)
H16—O2—H17	105.0	C9—C10—C11	111.3 (5)
O1—C1—N1	118.2 (6)	C12—C10—C11	107.9 (5)
O1—C1—C2	125.6 (6)	C9—C10—H10	108.9
N1—C1—C2	116.2 (5)	C12—C10—H10	108.9
C3—C2—C1	120.2 (6)	C11—C10—H10	108.9
C3—C2—H2	119.9	C5—C11—C10	110.2 (5)
C1—C2—H2	119.9	C5—C11—H11A	109.6
C2—C3—C4	121.9 (6)	C10—C11—H11A	109.6
C2—C3—H3	119.0	C5—C11—H11B	109.6
C4—C3—H3	119.0	C10—C11—H11B	109.6
C5—C4—C3	117.9 (6)	H11A—C11—H11B	108.1
C5—C4—C6	121.0 (5)	C14—C12—C6	125.8 (6)
C3—C4—C6	121.1 (6)	C14—C12—C10	124.2 (6)
C4—C5—N1	119.2 (5)	C6—C12—C10	109.9 (6)
C4—C5—C11	125.6 (5)	C8—C13—H13A	109.5
N1—C5—C11	115.2 (5)	C8—C13—H13B	109.5
N2—C6—C12	113.2 (5)	H13A—C13—H13B	109.5
N2—C6—C7	108.6 (5)	C8—C13—H13C	109.5
C12—C6—C7	108.6 (5)	H13A—C13—H13C	109.5
N2—C6—C4	109.5 (5)	H13B—C13—H13C	109.5
C12—C6—C4	108.1 (5)	C12—C14—C15	129.0 (7)
C7—C6—C4	108.7 (5)	C12—C14—H14	115.5
C8—C7—C6	114.9 (5)	C15—C14—H14	115.5
C8—C7—H7A	108.5	C14—C15—H15A	109.5
C6—C7—H7A	108.5	C14—C15—H15B	109.5
C8—C7—H7B	108.5	H15A—C15—H15B	109.5
C6—C7—H7B	108.5	C14—C15—H15C	109.5
H7A—C7—H7B	107.5	H15A—C15—H15C	109.5
C9—C8—C13	122.4 (7)	H15B—C15—H15C	109.5
C5—N1—C1—O1	−179.7 (6)	C6—C7—C8—C9	11.2 (9)
C5—N1—C1—C2	0.6 (9)	C6—C7—C8—C13	−168.6 (6)
O1—C1—C2—C3	−179.9 (7)	C13—C8—C9—C10	−179.6 (6)
N1—C1—C2—C3	−0.2 (10)	C7—C8—C9—C10	0.7 (9)
C1—C2—C3—C4	−0.2 (11)	C8—C9—C10—C12	19.4 (7)
C2—C3—C4—C5	0.3 (10)	C8—C9—C10—C11	−100.7 (7)
C2—C3—C4—C6	178.9 (6)	C4—C5—C11—C10	13.2 (9)
C3—C4—C5—N1	0.1 (9)	N1—C5—C11—C10	−167.8 (5)
C6—C4—C5—N1	−178.5 (5)	C9—C10—C11—C5	75.4 (7)
C3—C4—C5—C11	179.1 (7)	C12—C10—C11—C5	−46.4 (7)
C6—C4—C5—C11	0.5 (10)	N2—C6—C12—C14	2.6 (9)
C1—N1—C5—C4	−0.5 (9)	C7—C6—C12—C14	−118.0 (7)
C1—N1—C5—C11	−179.6 (6)	C4—C6—C12—C14	124.2 (7)
C5—C4—C6—N2	143.9 (6)	N2—C6—C12—C10	−176.6 (5)
C3—C4—C6—N2	−34.6 (8)	C7—C6—C12—C10	62.7 (6)
C5—C4—C6—C12	20.2 (8)	C4—C6—C12—C10	−55.0 (6)
C3—C4—C6—C12	−158.4 (6)	C9—C10—C12—C14	129.5 (6)
C5—C4—C6—C7	−97.6 (7)	C11—C10—C12—C14	−108.4 (7)
C3—C4—C6—C7	83.8 (7)	C9—C10—C12—C6	−51.2 (6)
N2—C6—C7—C8	−166.0 (5)	C11—C10—C12—C6	70.9 (6)
C12—C6—C7—C8	−42.5 (7)	C6—C12—C14—C15	−178.4 (7)
C4—C6—C7—C8	74.9 (7)	C10—C12—C14—C15	0.7 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H17···O2^i	0.85	2.42	2.833 (13)	111
O2—H16···O1^ii	0.85	2.03	2.877 (9)	174
N2—H2B···O2^iii	0.86	2.07	2.918 (9)	168
N2—H2A···N2^iv	0.86	2.68	3.333 (12)	134
N1—H1···O1^v	0.86	1.94	2.780 (8)	165

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