t-3-Methyl-1-nitroso-r-2,c-6-diphenyl­piperidin-4-one oxime monohydrate

In the title compound, C₁₈H₁₉N₃O₂·H₂O, the piperidine ring adopts a distorted boat conformation. In the solid state, the mol­ecules are linked by inter­molecular O—H...O and O—H...N hydrogen bonds involving water mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.136
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.33
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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               1665
           Count of symmetry unique reflns         1666
           Completeness (_total/calc)             99.94%
           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
   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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 QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

t-3-Methyl-1-nitroso-r-2,c-6-diphenylpiperidin-4-one oxime monohydrate

Crystal data

C18H19N3O2·H2O	F(000) = 348
Mr = 327.38	Dx = 1.259 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3835 reflections
a = 7.9578 (13) Å	θ = 2.6–25.0°
b = 7.0567 (12) Å	µ = 0.09 mm^−1
c = 15.642 (3) Å	T = 273 K
β = 100.483 (3)°	Block, colourless
V = 863.7 (3) Å^3	0.24 × 0.24 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area detector diffractometer	1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
ω scans	h = −9→9
8200 measured reflections	k = −8→8
1665 independent reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1019P)^2 + 0.0428P] where P = (Fo^2 + 2Fc^2)/3
1665 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.26 e Å^−3
1 restraint	Δρmin = −0.16 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
O22	0.9311 (3)	0.2590 (5)	0.15111 (19)	0.0774 (8)
O24	0.2842 (3)	0.8051 (3)	0.12109 (16)	0.0589 (6)
H24	0.2169	0.8667	0.0859	0.088*
N1	0.6840 (3)	0.2866 (4)	0.18680 (15)	0.0451 (6)
N21	0.7978 (3)	0.1772 (5)	0.16049 (19)	0.0615 (7)
N23	0.2642 (3)	0.6139 (4)	0.10156 (16)	0.0483 (6)
C6	0.7090 (3)	0.4937 (4)	0.19281 (18)	0.0443 (7)
H6	0.7400	0.5369	0.1382	0.053*
C5	0.5412 (4)	0.5908 (4)	0.2020 (2)	0.0509 (7)
H5A	0.5225	0.5744	0.2611	0.061*
H5B	0.5513	0.7256	0.1919	0.061*
C4	0.3887 (3)	0.5149 (4)	0.14017 (17)	0.0418 (6)
C3	0.3815 (4)	0.3047 (4)	0.12035 (18)	0.0448 (7)
H3	0.2681	0.2581	0.1261	0.054*
C2	0.5152 (4)	0.1968 (4)	0.18555 (19)	0.0444 (6)
H2	0.5225	0.0697	0.1612	0.053*
C7	0.4070 (5)	0.2660 (5)	0.0274 (2)	0.0592 (8)
H7A	0.3239	0.3358	−0.0126	0.089*
H7B	0.3934	0.1329	0.0153	0.089*
H7C	0.5198	0.3048	0.0212	0.089*
C14	0.4809 (4)	0.1687 (4)	0.27671 (19)	0.0481 (7)
C19	0.5957 (5)	0.0583 (5)	0.3331 (2)	0.0650 (9)
H19	0.6914	0.0091	0.3146	0.078*
C18	0.5704 (7)	0.0211 (7)	0.4153 (3)	0.0814 (13)
H18	0.6489	−0.0533	0.4520	0.098*
C17	0.4304 (7)	0.0920 (8)	0.4443 (3)	0.0869 (14)
H17	0.4140	0.0675	0.5007	0.104*
C16	0.3159 (6)	0.1991 (7)	0.3893 (3)	0.0788 (12)
H16	0.2207	0.2473	0.4087	0.095*
C15	0.3378 (5)	0.2375 (5)	0.3055 (2)	0.0593 (8)
H15	0.2572	0.3091	0.2686	0.071*
C8	0.8504 (3)	0.5547 (4)	0.26659 (19)	0.0458 (7)
C9	0.9748 (4)	0.6789 (6)	0.2478 (2)	0.0607 (8)
H9	0.9740	0.7161	0.1907	0.073*
C10	1.0992 (5)	0.7470 (6)	0.3140 (3)	0.0763 (12)
H10	1.1841	0.8267	0.3009	0.092*
C11	1.0984 (5)	0.6979 (7)	0.3982 (3)	0.0758 (11)
H11	1.1802	0.7479	0.4425	0.091*
C12	0.9767 (5)	0.5744 (7)	0.4178 (2)	0.0753 (11)
H12	0.9782	0.5378	0.4750	0.090*
C13	0.8519 (4)	0.5047 (6)	0.3515 (2)	0.0615 (9)
H13	0.7684	0.4234	0.3648	0.074*
O1W	1.0323 (4)	0.0041 (5)	0.0310 (3)	0.0838 (9)
H1W	0.971 (7)	0.022 (8)	−0.020 (4)	0.087 (14)*
H2W	0.990 (10)	0.074 (14)	0.061 (5)	0.14 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O22	0.0433 (12)	0.088 (2)	0.1031 (18)	0.0014 (13)	0.0200 (11)	−0.0235 (16)
O24	0.0449 (12)	0.0432 (12)	0.0843 (15)	0.0035 (9)	0.0008 (10)	−0.0009 (11)
N1	0.0366 (12)	0.0400 (13)	0.0567 (13)	0.0044 (10)	0.0034 (9)	−0.0015 (11)
N21	0.0461 (15)	0.0614 (17)	0.0770 (17)	0.0097 (13)	0.0112 (12)	−0.0101 (14)
N23	0.0403 (13)	0.0444 (13)	0.0602 (14)	0.0010 (11)	0.0090 (10)	−0.0010 (12)
C6	0.0359 (14)	0.0454 (16)	0.0504 (14)	−0.0017 (12)	0.0043 (11)	0.0019 (12)
C5	0.0433 (15)	0.0335 (14)	0.0725 (18)	0.0023 (12)	0.0018 (13)	−0.0027 (13)
C4	0.0340 (13)	0.0432 (15)	0.0470 (13)	0.0008 (11)	0.0041 (10)	0.0026 (12)
C3	0.0375 (14)	0.0426 (15)	0.0519 (15)	−0.0048 (12)	0.0013 (11)	−0.0003 (13)
C2	0.0421 (14)	0.0325 (13)	0.0570 (15)	−0.0036 (12)	0.0045 (11)	−0.0039 (12)
C7	0.0655 (19)	0.0495 (18)	0.0593 (17)	0.0020 (15)	0.0022 (14)	−0.0058 (15)
C14	0.0523 (16)	0.0343 (14)	0.0538 (15)	−0.0087 (12)	−0.0011 (12)	−0.0010 (12)
C19	0.067 (2)	0.052 (2)	0.071 (2)	−0.0038 (17)	−0.0016 (16)	0.0114 (17)
C18	0.102 (3)	0.070 (2)	0.064 (2)	−0.016 (2)	−0.008 (2)	0.016 (2)
C17	0.127 (4)	0.079 (3)	0.0541 (19)	−0.034 (3)	0.015 (2)	0.002 (2)
C16	0.097 (3)	0.077 (3)	0.070 (2)	−0.015 (2)	0.032 (2)	−0.015 (2)
C15	0.0636 (19)	0.0517 (19)	0.0638 (18)	−0.0028 (16)	0.0147 (15)	−0.0050 (15)
C8	0.0334 (13)	0.0438 (16)	0.0588 (16)	−0.0004 (12)	0.0044 (11)	−0.0018 (13)
C9	0.0513 (17)	0.061 (2)	0.0693 (19)	−0.0147 (16)	0.0097 (14)	−0.0013 (17)
C10	0.053 (2)	0.074 (3)	0.099 (3)	−0.028 (2)	0.0081 (18)	−0.012 (2)
C11	0.0537 (19)	0.078 (3)	0.085 (3)	−0.013 (2)	−0.0137 (17)	−0.021 (2)
C12	0.073 (2)	0.087 (3)	0.0606 (19)	−0.009 (2)	−0.0028 (16)	0.000 (2)
C13	0.0532 (18)	0.063 (2)	0.0647 (19)	−0.0127 (16)	0.0022 (14)	−0.0001 (17)
O1W	0.0624 (17)	0.081 (2)	0.096 (2)	0.0290 (15)	−0.0195 (14)	−0.0191 (17)

Geometric parameters (Å, º)

O22—N21	1.240 (4)	C14—C19	1.388 (5)
O24—N23	1.386 (4)	C19—C18	1.362 (6)
O24—H24	0.82	C19—H19	0.93
N1—N21	1.312 (4)	C18—C17	1.373 (8)
N1—C6	1.475 (4)	C18—H18	0.93
N1—C2	1.482 (4)	C17—C16	1.362 (7)
N23—C4	1.271 (4)	C17—H17	0.93
C6—C8	1.520 (4)	C16—C15	1.382 (5)
C6—C5	1.531 (4)	C16—H16	0.93
C6—H6	0.98	C15—H15	0.93
C5—C4	1.507 (4)	C8—C13	1.372 (5)
C5—H5A	0.97	C8—C9	1.393 (5)
C5—H5B	0.97	C9—C10	1.382 (5)
C4—C3	1.514 (4)	C9—H9	0.93
C3—C7	1.529 (4)	C10—C11	1.363 (6)
C3—C2	1.535 (4)	C10—H10	0.93
C3—H3	0.98	C11—C12	1.378 (6)
C2—C14	1.513 (4)	C11—H11	0.93
C2—H2	0.98	C12—C13	1.389 (5)
C7—H7A	0.96	C12—H12	0.93
C7—H7B	0.96	C13—H13	0.93
C7—H7C	0.96	O1W—H1W	0.87 (6)
C14—C15	1.386 (5)	O1W—H2W	0.80 (8)
N23—O24—H24	109.5	H7B—C7—H7C	109.5
N21—N1—C6	120.7 (3)	C15—C14—C19	118.4 (3)
N21—N1—C2	114.8 (2)	C15—C14—C2	124.0 (3)
C6—N1—C2	122.4 (2)	C19—C14—C2	117.5 (3)
O22—N21—N1	114.7 (3)	C18—C19—C14	121.0 (4)
C4—N23—O24	112.5 (2)	C18—C19—H19	119.5
N1—C6—C8	113.7 (2)	C14—C19—H19	119.5
N1—C6—C5	109.8 (2)	C19—C18—C17	120.7 (4)
C8—C6—C5	109.8 (2)	C19—C18—H18	119.7
N1—C6—H6	107.8	C17—C18—H18	119.7
C8—C6—H6	107.8	C16—C17—C18	118.9 (4)
C5—C6—H6	107.8	C16—C17—H17	120.6
C4—C5—C6	113.3 (3)	C18—C17—H17	120.6
C4—C5—H5A	108.9	C17—C16—C15	121.5 (4)
C6—C5—H5A	108.9	C17—C16—H16	119.2
C4—C5—H5B	108.9	C15—C16—H16	119.2
C6—C5—H5B	108.9	C16—C15—C14	119.5 (4)
H5A—C5—H5B	107.7	C16—C15—H15	120.3
N23—C4—C5	125.2 (3)	C14—C15—H15	120.3
N23—C4—C3	116.4 (3)	C13—C8—C9	119.0 (3)
C5—C4—C3	118.4 (2)	C13—C8—C6	122.4 (3)
C4—C3—C7	111.3 (3)	C9—C8—C6	118.3 (3)
C4—C3—C2	110.7 (2)	C10—C9—C8	120.0 (3)
C7—C3—C2	110.3 (3)	C10—C9—H9	120.0
C4—C3—H3	108.1	C8—C9—H9	120.0
C7—C3—H3	108.1	C11—C10—C9	120.4 (3)
C2—C3—H3	108.1	C11—C10—H10	119.8
N1—C2—C14	111.2 (2)	C9—C10—H10	119.8
N1—C2—C3	108.3 (2)	C10—C11—C12	120.2 (3)
C14—C2—C3	118.0 (2)	C10—C11—H11	119.9
N1—C2—H2	106.2	C12—C11—H11	119.9
C14—C2—H2	106.2	C11—C12—C13	119.6 (4)
C3—C2—H2	106.2	C11—C12—H12	120.2
C3—C7—H7A	109.5	C13—C12—H12	120.2
C3—C7—H7B	109.5	C8—C13—C12	120.7 (3)
H7A—C7—H7B	109.5	C8—C13—H13	119.6
C3—C7—H7C	109.5	C12—C13—H13	119.6
H7A—C7—H7C	109.5	H1W—O1W—H2W	103 (7)
C6—N1—N21—O22	7.5 (4)	N1—C2—C14—C15	124.6 (3)
C2—N1—N21—O22	171.3 (3)	C3—C2—C14—C15	−1.3 (4)
N21—N1—C6—C8	−70.9 (4)	N1—C2—C14—C19	−59.0 (3)
C2—N1—C6—C8	126.5 (3)	C3—C2—C14—C19	175.1 (3)
N21—N1—C6—C5	165.6 (3)	C15—C14—C19—C18	−1.1 (5)
C2—N1—C6—C5	3.0 (4)	C2—C14—C19—C18	−177.7 (3)
N1—C6—C5—C4	−45.0 (3)	C14—C19—C18—C17	0.0 (6)
C8—C6—C5—C4	−170.8 (3)	C19—C18—C17—C16	0.7 (7)
O24—N23—C4—C5	1.1 (4)	C18—C17—C16—C15	−0.1 (7)
O24—N23—C4—C3	−177.9 (2)	C17—C16—C15—C14	−1.1 (6)
C6—C5—C4—N23	−141.9 (3)	C19—C14—C15—C16	1.7 (5)
C6—C5—C4—C3	37.1 (4)	C2—C14—C15—C16	178.0 (3)
N23—C4—C3—C7	69.8 (3)	N1—C6—C8—C13	−56.1 (4)
C5—C4—C3—C7	−109.3 (3)	C5—C6—C8—C13	67.5 (4)
N23—C4—C3—C2	−167.1 (2)	N1—C6—C8—C9	129.4 (3)
C5—C4—C3—C2	13.8 (4)	C5—C6—C8—C9	−107.0 (3)
N21—N1—C2—C14	112.2 (3)	C13—C8—C9—C10	1.3 (5)
C6—N1—C2—C14	−84.3 (3)	C6—C8—C9—C10	176.0 (4)
N21—N1—C2—C3	−116.7 (3)	C8—C9—C10—C11	−2.0 (7)
C6—N1—C2—C3	46.9 (3)	C9—C10—C11—C12	2.3 (7)
C4—C3—C2—N1	−53.1 (3)	C10—C11—C12—C13	−1.9 (7)
C7—C3—C2—N1	70.5 (3)	C9—C8—C13—C12	−0.9 (5)
C4—C3—C2—C14	74.3 (3)	C6—C8—C13—C12	−175.4 (3)
C7—C3—C2—C14	−162.1 (3)	C11—C12—C13—C8	1.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···O1W^i	0.82	1.84	2.636 (4)	164
O1W—H1W···N23^ii	0.87 (6)	2.16 (6)	2.947 (4)	150 (5)
O1W—H2W···O22	0.80 (8)	2.03 (9)	2.822 (5)	169 (8)
O1W—H2W···N21	0.80 (8)	2.48 (8)	3.233 (5)	158 (8)

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