4′-[(2-Butyl-4-oxo-1,3-di­aza­spiro­[4.4]­non-1-en-3-yl)­methyl]-1,1′-bi­phenyl-2-carbo­nitrile 0.25-hydrate

Song, Q.B.; Hu, Y.H.; Shen, T.H.; Jin, Z.M.

doi:10.1107/S1600536804008463

4′-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1′-biphenyl-2-carbonitrile 0.25-hydrate

Q. B. Song, Y. H. Hu, T. H. Shen and Z. M. Jin

In the title compound, C₂₅H₂₇N₃O·0.25H₂O, the minimum and maximum C—C bond lengths in the cyclopentane ring are 1.444 (3) and 1.489 (3) Å, respectively. In the crystal structure, molecules are linked by weak intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008463/lh6182sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008463/lh6182Isup2.hkl Contains datablock I

CCDC reference: 242029

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.056
wR factor = 0.118
Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1'-biphenyl- 2-carbonitrile–water (4/1) top

Crystal data top

C₂₅H₂₇N₃O·0.25H₂O	Z = 2
M_r = 390.00	F(000) = 417
Triclinic, P1	D_x = 1.201 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1419 (13) Å	Cell parameters from 831 reflections
b = 10.0656 (14) Å	θ = 2.5–21.4°
c = 12.1721 (17) Å	µ = 0.08 mm⁻¹
α = 90.438 (3)°	T = 293 K
β = 105.110 (3)°	Prism, colorless
γ = 94.126 (3)°	0.32 × 0.28 × 0.20 mm
V = 1078.1 (3) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3713 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
T_min = 0.97, T_max = 0.98	k = −11→11
5382 measured reflections	l = −13→14

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
3713 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.37120 (14)	0.35422 (13)	0.40617 (10)	0.0532 (3)
N1	0.52565 (16)	0.37240 (14)	0.28629 (12)	0.0453 (3)
N2	0.39725 (17)	0.24482 (14)	0.13523 (13)	0.0472 (4)
N3	1.06784 (19)	0.38612 (17)	0.85448 (15)	0.0560 (4)
C1	0.6525 (2)	0.45808 (18)	0.35922 (16)	0.0502 (4)
H1A	0.6129	0.5131	0.4089	0.060*
H1B	0.6959	0.5170	0.3113	0.060*
C2	0.77747 (18)	0.37985 (17)	0.43166 (14)	0.0437 (4)
C3	0.75036 (19)	0.31504 (18)	0.52482 (15)	0.0480 (4)
H3	0.6567	0.3187	0.5410	0.058*
C4	0.86288 (19)	0.24395 (18)	0.59507 (16)	0.0485 (4)
H4	0.8451	0.2005	0.6581	0.058*
C5	0.99929 (19)	0.23956 (16)	0.56934 (14)	0.0413 (4)
C6	1.0261 (2)	0.30255 (17)	0.47521 (15)	0.0464 (4)
H6	1.1189	0.2979	0.4579	0.056*
C7	0.9140 (2)	0.37220 (17)	0.40729 (16)	0.0483 (4)
H7	0.9317	0.4146	0.3439	0.058*
C8	1.1098 (2)	0.16348 (17)	0.64605 (15)	0.0472 (4)
C9	1.1533 (2)	0.18984 (17)	0.76350 (15)	0.0458 (4)
C10	1.2592 (2)	0.11897 (19)	0.83336 (17)	0.0526 (5)
H10A	1.2848	0.1358	0.9115	0.063*
C11	1.3283 (2)	0.0237 (2)	0.78982 (18)	0.0551 (5)
H11A	1.4005	−0.0240	0.8386	0.066*
C12	1.2926 (2)	−0.00268 (19)	0.67504 (18)	0.0559 (5)
H12A	1.3331	−0.0738	0.6472	0.067*
C13	1.1821 (2)	0.06690 (18)	0.60405 (16)	0.0504 (4)
H13A	1.1559	0.0481	0.5261	0.060*
C14	1.1076 (2)	0.30021 (19)	0.81408 (16)	0.0486 (4)
C15	0.51656 (18)	0.32003 (16)	0.17759 (14)	0.0395 (4)
C16	0.30514 (19)	0.24000 (17)	0.21733 (15)	0.0440 (4)
C17	0.3814 (2)	0.33082 (18)	0.31310 (16)	0.0495 (4)
C18	0.15181 (19)	0.2832 (2)	0.18066 (17)	0.0533 (5)
H18A	0.1466	0.3518	0.1245	0.064*
H18B	0.1216	0.3190	0.2449	0.064*
C19	0.0506 (2)	0.16347 (18)	0.13041 (19)	0.0605 (5)
H19A	−0.0387	0.1581	0.1596	0.073*
H19B	0.0175	0.1703	0.0483	0.073*
C20	0.1314 (2)	0.0452 (2)	0.1591 (2)	0.0624 (5)
H20A	0.1596	0.0080	0.0944	0.075*
H20B	0.0738	−0.0225	0.1901	0.075*
C21	0.2639 (2)	0.10385 (18)	0.24555 (17)	0.0526 (4)
H21A	0.2412	0.1045	0.3191	0.063*
H21B	0.3491	0.0499	0.2507	0.063*
C22	0.6418 (2)	0.35770 (18)	0.12222 (16)	0.0482 (4)
H22A	0.7338	0.3186	0.1630	0.058*	0.832 (10)
H22B	0.6623	0.4538	0.1264	0.058*	0.832 (10)
C23	0.5983 (5)	0.3089 (4)	−0.0045 (3)	0.0444 (8)	0.832 (10)
H23A	0.5983	0.2126	−0.0081	0.053*	0.832 (10)
H23B	0.4965	0.3326	−0.0414	0.053*	0.832 (10)
C24	0.7061 (5)	0.3687 (3)	−0.0660 (3)	0.0461 (8)	0.832 (10)
H24A	0.8073	0.3429	−0.0299	0.055*	0.832 (10)
H24B	0.7085	0.4650	−0.0597	0.055*	0.832 (10)
C25	0.6649 (8)	0.3269 (6)	−0.1915 (6)	0.0436 (12)	0.832 (10)
H25A	0.6972	0.2394	−0.1993	0.065*	0.832 (10)
H25B	0.7147	0.3890	−0.2320	0.065*	0.832 (10)
H25C	0.5569	0.3258	−0.2223	0.065*	0.832 (10)
H22C	0.7376	0.3551	0.1797	0.058*	0.168 (10)
H22D	0.6328	0.4495	0.0994	0.058*	0.168 (10)
C23'	0.652 (2)	0.2727 (14)	0.0161 (14)	0.044 (4)	0.168 (10)
H23C	0.5734	0.1998	0.0007	0.053*	0.168 (10)
H23D	0.7499	0.2354	0.0311	0.053*	0.168 (10)
C25'	0.632 (4)	0.297 (3)	−0.206 (3)	0.030 (4)	0.168 (10)
H25D	0.6691	0.2102	−0.1900	0.045*	0.168 (10)
H25E	0.6981	0.3483	−0.2425	0.045*	0.168 (10)
H25F	0.5314	0.2875	−0.2559	0.045*	0.168 (10)
C24'	0.630 (3)	0.3685 (13)	−0.0937 (12)	0.046 (4)	0.168 (10)
H24C	0.5336	0.4083	−0.1049	0.055*	0.168 (10)
H24D	0.7098	0.4402	−0.0768	0.055*	0.168 (10)
O1W	0.5006 (6)	0.0870 (5)	0.4997 (4)	0.0515 (12)	0.25
H1WC	0.4595	0.0287	0.4478	0.062*	0.25
H1WB	0.4349	0.1102	0.5328	0.062*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0520 (7)	0.0646 (7)	0.0430 (7)	−0.0001 (6)	0.0136 (6)	−0.0054 (6)
N1	0.0445 (8)	0.0501 (8)	0.0412 (8)	0.0040 (6)	0.0113 (6)	−0.0010 (6)
N2	0.0498 (8)	0.0490 (8)	0.0445 (8)	−0.0017 (6)	0.0166 (6)	0.0025 (7)
N3	0.0503 (8)	0.0558 (9)	0.0587 (10)	0.0060 (7)	0.0081 (7)	−0.0032 (8)
C1	0.0520 (10)	0.0541 (10)	0.0457 (10)	−0.0003 (8)	0.0164 (8)	−0.0008 (8)
C2	0.0430 (9)	0.0493 (9)	0.0378 (9)	−0.0058 (7)	0.0115 (7)	0.0011 (7)
C3	0.0372 (9)	0.0586 (10)	0.0473 (10)	0.0023 (8)	0.0095 (8)	0.0001 (8)
C4	0.0445 (9)	0.0566 (10)	0.0441 (10)	0.0040 (8)	0.0108 (8)	−0.0011 (8)
C5	0.0484 (9)	0.0351 (8)	0.0408 (9)	0.0027 (7)	0.0126 (7)	−0.0014 (7)
C6	0.0500 (10)	0.0482 (9)	0.0439 (9)	0.0040 (8)	0.0175 (8)	−0.0029 (7)
C7	0.0518 (10)	0.0446 (9)	0.0511 (10)	0.0051 (8)	0.0178 (8)	0.0011 (8)
C8	0.0505 (10)	0.0480 (9)	0.0456 (10)	0.0018 (8)	0.0176 (8)	0.0025 (7)
C9	0.0478 (9)	0.0433 (8)	0.0472 (10)	0.0010 (7)	0.0149 (8)	0.0046 (8)
C10	0.0550 (10)	0.0573 (11)	0.0462 (10)	−0.0025 (9)	0.0164 (8)	0.0001 (9)
C11	0.0482 (10)	0.0571 (11)	0.0591 (12)	0.0053 (8)	0.0119 (9)	0.0020 (9)
C12	0.0505 (11)	0.0530 (10)	0.0615 (12)	0.0124 (9)	0.0078 (9)	−0.0026 (9)
C13	0.0505 (10)	0.0548 (10)	0.0446 (10)	0.0100 (8)	0.0088 (8)	−0.0011 (8)
C14	0.0496 (9)	0.0525 (10)	0.0438 (10)	0.0023 (8)	0.0128 (8)	0.0020 (8)
C15	0.0380 (8)	0.0406 (8)	0.0407 (9)	0.0054 (7)	0.0109 (7)	0.0035 (7)
C16	0.0414 (9)	0.0488 (9)	0.0423 (9)	0.0043 (7)	0.0120 (7)	0.0020 (7)
C17	0.0576 (11)	0.0500 (10)	0.0429 (10)	0.0052 (8)	0.0167 (8)	0.0004 (8)
C18	0.0405 (9)	0.0652 (11)	0.0530 (11)	0.0009 (8)	0.0111 (8)	0.0012 (9)
C19	0.0529 (11)	0.0509 (10)	0.0677 (13)	−0.0009 (8)	−0.0008 (9)	0.0054 (9)
C20	0.0515 (11)	0.0567 (11)	0.0747 (14)	−0.0072 (9)	0.0119 (10)	0.0010 (10)
C21	0.0570 (11)	0.0487 (10)	0.0529 (11)	0.0045 (8)	0.0154 (9)	0.0077 (8)
C22	0.0463 (10)	0.0518 (10)	0.0497 (10)	0.0024 (8)	0.0182 (8)	0.0004 (8)
C23	0.0577 (19)	0.0371 (17)	0.0381 (14)	−0.0002 (13)	0.0128 (14)	0.0041 (12)
C24	0.0479 (18)	0.0517 (13)	0.0403 (17)	0.0068 (13)	0.0138 (14)	0.0041 (11)
C25	0.048 (3)	0.037 (3)	0.041 (3)	0.0008 (18)	0.005 (2)	0.006 (2)
C23'	0.056 (8)	0.026 (6)	0.046 (7)	0.027 (5)	0.000 (6)	0.009 (5)
C25'	0.041 (12)	0.014 (8)	0.027 (7)	−0.005 (6)	−0.004 (7)	−0.004 (6)
C24'	0.056 (10)	0.034 (5)	0.039 (7)	0.018 (7)	−0.006 (7)	0.009 (5)
O1W	0.056 (3)	0.054 (3)	0.041 (3)	0.006 (2)	0.007 (2)	0.003 (2)

Geometric parameters (Å, º) top

O1—C17	1.184 (2)	C16—C17	1.466 (2)
N1—C15	1.400 (2)	C18—C19	1.489 (3)
N1—C17	1.472 (2)	C18—H18A	0.9700
N1—C1	1.478 (2)	C18—H18B	0.9700
N2—C15	1.269 (2)	C19—C20	1.444 (3)
N2—C16	1.464 (2)	C19—H19A	0.9700
N3—C14	1.119 (2)	C19—H19B	0.9700
C1—C2	1.522 (2)	C20—C21	1.465 (3)
C1—H1A	0.9700	C20—H20A	0.9700
C1—H1B	0.9700	C20—H20B	0.9700
C2—C7	1.363 (2)	C21—H21A	0.9700
C2—C3	1.381 (2)	C21—H21B	0.9700
C3—C4	1.399 (2)	C22—C23	1.555 (3)
C3—H3	0.9300	C22—H22A	0.9700
C4—C5	1.366 (2)	C22—H22B	0.9700
C4—H4	0.9300	C23—C24	1.484 (4)
C5—C6	1.382 (2)	C23—H23A	0.9700
C5—C8	1.452 (2)	C23—H23B	0.9700
C6—C7	1.377 (2)	C24—C25	1.523 (7)
C6—H6	0.9300	C24—H24A	0.9700
C7—H7	0.9300	C24—H24B	0.9700
C8—C13	1.380 (3)	C25—H25A	0.9600
C8—C9	1.398 (2)	C25—H25B	0.9600
C9—C10	1.360 (3)	C25—H25C	0.9600
C9—C14	1.406 (3)	C23'—C24'	1.63 (2)
C10—C11	1.361 (3)	C23'—H23C	0.9700
C10—H10A	0.9300	C23'—H23D	0.9700
C11—C12	1.369 (3)	C25'—C24'	1.55 (3)
C11—H11A	0.9300	C25'—H25D	0.9600
C12—C13	1.383 (2)	C25'—H25E	0.9600
C12—H12A	0.9300	C25'—H25F	0.9600
C13—H13A	0.9300	C24'—H24C	0.9700
C15—C22	1.501 (2)	C24'—H24D	0.9700
C16—C18	1.455 (2)	O1W—H1WC	0.8500
C16—C21	1.462 (2)	O1W—H1WB	0.8500

C15—N1—C17	107.06 (14)	C16—C18—H18A	110.4
C15—N1—C1	126.97 (14)	C19—C18—H18A	110.4
C17—N1—C1	125.92 (14)	C16—C18—H18B	110.4
C15—N2—C16	107.76 (15)	C19—C18—H18B	110.4
N1—C1—C2	113.35 (14)	H18A—C18—H18B	108.6
N1—C1—H1A	108.9	C20—C19—C18	109.65 (16)
C2—C1—H1A	108.9	C20—C19—H19A	109.7
N1—C1—H1B	108.9	C18—C19—H19A	109.7
C2—C1—H1B	108.9	C20—C19—H19B	109.7
H1A—C1—H1B	107.7	C18—C19—H19B	109.7
C7—C2—C3	119.51 (17)	H19A—C19—H19B	108.2
C7—C2—C1	122.09 (16)	C19—C20—C21	98.86 (16)
C3—C2—C1	118.41 (15)	C19—C20—H20A	112.0
C2—C3—C4	120.42 (16)	C21—C20—H20A	112.0
C2—C3—H3	119.8	C19—C20—H20B	112.0
C4—C3—H3	119.8	C21—C20—H20B	112.0
C5—C4—C3	118.72 (17)	H20A—C20—H20B	109.7
C5—C4—H4	120.6	C16—C21—C20	110.92 (16)
C3—C4—H4	120.6	C16—C21—H21A	109.5
C4—C5—C6	121.05 (17)	C20—C21—H21A	109.5
C4—C5—C8	115.38 (16)	C16—C21—H21B	109.5
C6—C5—C8	123.56 (16)	C20—C21—H21B	109.5
C7—C6—C5	119.33 (16)	H21A—C21—H21B	108.0
C7—C6—H6	120.3	C15—C22—C23	111.12 (17)
C5—C6—H6	120.3	C15—C22—H22A	109.4
C2—C7—C6	120.96 (17)	C23—C22—H22A	109.4
C2—C7—H7	119.5	C15—C22—H22B	109.4
C6—C7—H7	119.5	C23—C22—H22B	109.4
C13—C8—C9	117.56 (17)	H22A—C22—H22B	108.0
C13—C8—C5	120.58 (16)	C24—C23—C22	111.4 (3)
C9—C8—C5	121.77 (16)	C24—C23—H23A	109.3
C10—C9—C8	120.67 (17)	C22—C23—H23A	109.3
C10—C9—C14	116.03 (17)	C24—C23—H23B	109.3
C8—C9—C14	122.74 (17)	C22—C23—H23B	109.3
C9—C10—C11	120.57 (18)	H23A—C23—H23B	108.0
C9—C10—H10A	119.7	C23—C24—C25	113.2 (3)
C11—C10—H10A	119.7	C23—C24—H24A	108.9
C10—C11—C12	120.74 (18)	C25—C24—H24A	108.9
C10—C11—H11A	119.6	C23—C24—H24B	108.9
C12—C11—H11A	119.6	C25—C24—H24B	108.9
C11—C12—C13	118.81 (18)	H24A—C24—H24B	107.8
C11—C12—H12A	119.7	C24'—C23'—H23C	109.9
C13—C12—H12A	121.0	C24'—C23'—H23D	109.9
C8—C13—C12	121.59 (18)	H23C—C23'—H23D	108.3
C8—C13—H13A	119.2	C24'—C25'—H25D	109.5
C12—C13—H13A	119.2	C24'—C25'—H25E	109.5
N3—C14—C9	178.2 (2)	H25D—C25'—H25E	109.5
N2—C15—N1	114.22 (15)	C24'—C25'—H25F	109.5
N2—C15—C22	126.63 (16)	H25D—C25'—H25F	109.5
N1—C15—C22	119.15 (15)	H25E—C25'—H25F	109.5
C18—C16—C21	97.33 (15)	C25'—C24'—C23'	114.7 (15)
C18—C16—N2	117.94 (15)	C25'—C24'—H24C	108.6
C21—C16—N2	112.73 (15)	C23'—C24'—H24C	108.6
C18—C16—C17	104.18 (14)	C25'—C24'—H24D	108.6
C21—C16—C17	116.59 (16)	C23'—C24'—H24D	108.6
N2—C16—C17	107.89 (14)	H24C—C24'—H24D	107.6
O1—C17—C16	137.42 (18)	O1Wⁱ—O1W—H1WC	49.4
O1—C17—N1	117.83 (16)	O1Wⁱ—O1W—H1WB	108.4
C16—C17—N1	102.60 (14)	H1WC—O1W—H1WB	109.5
C16—C18—C19	106.61 (16)

C4—C5—C8—C9	−54.7 (2)	C6—C5—C8—C13	−50.0 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱⁱ	0.97	2.57	3.474 (2)	154
C6—H6···O1ⁱⁱⁱ	0.93	2.57	3.477 (2)	164
C18—H18B···O1	0.97	2.59	2.994 (2)	105

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z.

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4′-[(2-Butyl-4-oxo-1,3-di­aza­spiro­[4.4]­non-1-en-3-yl)­methyl]-1,1′-bi­phenyl-2-carbo­nitrile 0.25-hydrate

Supporting information

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checkCIF/PLATON results

4′-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1′-biphenyl-2-carbonitrile 0.25-hydrate