3,5-Bis(2-fluoro­phen­yl)-1-isopropyl-1,3,5-triaza­cyclo­hexa­ne

In the crystal structure of the title compound, C₁₈H₂₁F₂N₃, the triaza­cyclo­hexane ring adopts a chair conformation with an equatorial–diaxial substitution pattern; there is an equatorial arrangement of the isopropyl group and the two 2-fluoro­phenyl substituents are in axial positions. The packing is stabilized by weak C—H...π inter­actions leading to the formation of chain parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 190 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 9.2

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           27.57
           From the CIF: _reflns_number_total               1929
           Count of symmetry unique reflns         1966
           Completeness (_total/calc)             98.12%
           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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C18H21F2N3	F(000) = 672
Mr = 317.38	Dx = 1.291 Mg m^−3
Orthorhombic, Pn21a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ac -2n	Cell parameters from 7973 reflections
a = 13.280 (1) Å	θ = 3.1–27.6°
b = 13.020 (1) Å	µ = 0.09 mm^−1
c = 9.4440 (2) Å	T = 190 K
V = 1632.92 (18) Å^3	Prism, colourless
Z = 4	0.60 × 0.33 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer	1812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.6°, θmin = 3.1°
φ scans, and ω scans with κ offsets	h = −17→15
7973 measured reflections	k = −10→16
1929 independent reflections	l = −9→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0821P)^2 + 0.2864P] where P = (Fo^2 + 2Fc^2)/3
1929 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.26 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
C1	0.88974 (12)	0.3150 (15)	0.1544 (2)	0.0288 (4)
H1A	0.8173	0.3141	0.1410	0.035*
H1B	0.9029	0.3124	0.2553	0.035*
C2	0.91700 (18)	0.4125 (15)	−0.0548 (3)	0.0333 (5)
H2A	0.9456	0.4754	−0.0925	0.040*
H2B	0.8457	0.4121	−0.0768	0.040*
C3	0.92145 (19)	0.2301 (15)	−0.0651 (3)	0.0325 (5)
H3A	0.8504	0.2275	−0.0885	0.039*
H3B	0.9540	0.1713	−0.1087	0.039*
C11	1.02810 (16)	0.1927 (15)	0.1397 (2)	0.0266 (5)
C12	1.11657 (18)	0.1898 (15)	0.0608 (2)	0.0310 (5)
H12	1.1156	0.2116	−0.0330	0.037*
C13	1.20631 (19)	0.1549 (15)	0.1192 (3)	0.0364 (6)
H13	1.2643	0.1534	0.0640	0.044*
C14	1.2105 (2)	0.1226 (15)	0.2580 (3)	0.0367 (6)
H14	1.2711	0.1008	0.2971	0.044*
C15	1.1233 (2)	0.1230 (15)	0.3386 (3)	0.0376 (6)
H15	1.1243	0.1009	0.4323	0.045*
C16	1.03565 (17)	0.1566 (15)	0.2780 (2)	0.0320 (5)
C21	0.96364 (19)	0.3326 (15)	−0.2785 (3)	0.0479 (7)
H21	0.9814	0.4040	−0.3001	0.057*
C31	1.02524 (16)	0.4422 (15)	0.1508 (2)	0.0277 (5)
C32	1.11136 (19)	0.4546 (15)	0.0680 (3)	0.0342 (5)
H32	1.1086	0.4404	−0.0285	0.041*
C33	1.2012 (2)	0.4880 (15)	0.1279 (3)	0.0399 (6)
H33	1.2577	0.4959	0.0708	0.048*
C34	1.2079 (2)	0.5096 (15)	0.2700 (3)	0.0420 (6)
H34	1.2686	0.5309	0.3093	0.050*
C35	1.1239 (2)	0.4993 (15)	0.3529 (3)	0.0432 (6)
H35	1.1269	0.5138	0.4492	0.052*
C36	1.03444 (19)	0.4671 (15)	0.2918 (2)	0.0350 (5)
C211	1.0445 (3)	0.2690 (15)	−0.3428 (3)	0.0622 (9)
H21A	1.0290	0.1976	−0.3298	0.093*
H21B	1.1075	0.2845	−0.2979	0.093*
H21C	1.0491	0.2839	−0.4421	0.093*
C212	0.8614 (2)	0.3151 (15)	−0.3462 (3)	0.0563 (7)
H21D	0.8648	0.3318	−0.4451	0.085*
H21E	0.8122	0.3580	−0.3009	0.085*
H21F	0.8425	0.2443	−0.3354	0.085*
N1	0.93335 (14)	0.2241 (15)	0.0873 (2)	0.0281 (4)
N2	0.96506 (13)	0.3247 (15)	−0.12231 (18)	0.0333 (4)
N3	0.93006 (14)	0.4110 (15)	0.0975 (2)	0.0289 (4)
F16	0.95039 (12)	0.1533 (15)	0.35724 (18)	0.0478 (5)
F36	0.95145 (13)	0.4609 (15)	0.37608 (16)	0.0534 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0238 (7)	0.0272 (9)	0.0354 (9)	−0.0008 (10)	0.0029 (6)	0.0022 (10)
C2	0.0364 (12)	0.0270 (11)	0.0365 (11)	0.0003 (9)	−0.0064 (9)	0.0048 (10)
C3	0.0370 (13)	0.0283 (11)	0.0322 (11)	−0.0013 (9)	−0.0078 (9)	−0.0027 (10)
C11	0.0286 (11)	0.0194 (9)	0.0316 (10)	−0.0002 (8)	0.0002 (8)	−0.0003 (8)
C12	0.0334 (11)	0.0283 (10)	0.0314 (10)	0.0010 (10)	0.0049 (9)	0.0012 (9)
C13	0.0299 (13)	0.0328 (12)	0.0467 (14)	0.0026 (9)	0.0067 (9)	0.0017 (11)
C14	0.0296 (13)	0.0344 (13)	0.0462 (13)	0.0028 (9)	−0.0052 (10)	−0.0010 (10)
C15	0.0372 (14)	0.0402 (13)	0.0353 (12)	0.0013 (10)	−0.0041 (10)	0.0058 (10)
C16	0.0265 (11)	0.0362 (11)	0.0332 (10)	−0.0008 (9)	0.0038 (8)	0.0046 (10)
C21	0.0575 (14)	0.0580 (19)	0.0281 (11)	−0.0032 (13)	−0.0041 (9)	0.0020 (11)
C31	0.0252 (11)	0.0229 (10)	0.0349 (10)	0.0013 (8)	0.0000 (8)	−0.0002 (8)
C32	0.0345 (12)	0.0312 (11)	0.0370 (11)	−0.0023 (10)	0.0045 (9)	−0.0020 (10)
C33	0.0286 (12)	0.0341 (13)	0.0569 (15)	−0.0025 (9)	0.0069 (10)	0.0015 (11)
C34	0.0301 (13)	0.0349 (13)	0.0611 (16)	−0.0006 (10)	−0.0126 (12)	−0.0045 (12)
C35	0.0419 (15)	0.0460 (15)	0.0415 (13)	−0.0013 (11)	−0.0082 (11)	−0.0095 (11)
C36	0.0314 (13)	0.0364 (12)	0.0373 (11)	−0.0026 (9)	0.0033 (9)	−0.0060 (11)
C211	0.086 (2)	0.060 (2)	0.0411 (16)	0.0066 (17)	0.0070 (14)	−0.0005 (14)
C212	0.0740 (16)	0.0584 (15)	0.0367 (12)	−0.0083 (18)	−0.0209 (11)	0.0042 (15)
N1	0.0282 (9)	0.0249 (9)	0.0313 (9)	−0.0002 (7)	−0.0017 (7)	0.0008 (7)
N2	0.0395 (9)	0.0334 (9)	0.0270 (8)	−0.0016 (10)	−0.0039 (6)	0.0016 (9)
N3	0.0272 (9)	0.0250 (9)	0.0343 (9)	0.0004 (7)	−0.0019 (7)	0.0007 (8)
F16	0.0347 (8)	0.0694 (11)	0.0395 (8)	0.0060 (8)	0.0099 (6)	0.0202 (8)
F36	0.0424 (9)	0.0767 (12)	0.0410 (8)	−0.0102 (9)	0.0132 (7)	−0.0211 (9)

Geometric parameters (Å, º)

F16—C16	1.358 (3)	C34—C35	1.369 (5)
F36—C36	1.362 (4)	C35—C36	1.386 (9)
N1—C1	1.46 (2)	C1—H1A	0.9700
N1—C3	1.450 (4)	C1—H1B	0.9700
N1—C11	1.413 (8)	C2—H2A	0.9700
N2—C2	1.46 (2)	C2—H2B	0.9700
N2—C3	1.46 (2)	C3—H3A	0.9700
N2—C21	1.479 (4)	C3—H3B	0.9700
N3—C1	1.46 (2)	C12—H12	0.9300
N3—C2	1.449 (3)	C13—H13	0.9300
N3—C31	1.420 (8)	C14—H14	0.9300
C11—C12	1.392 (3)	C15—H15	0.9300
C11—C16	1.392 (10)	C21—H21	0.9800
C12—C13	1.390 (10)	C32—H32	0.9300
C13—C14	1.378 (9)	C33—H33	0.9300
C14—C15	1.386 (4)	C34—H34	0.9300
C15—C16	1.369 (9)	C35—H35	0.9300
C21—C211	1.486 (16)	C211—H21A	0.9600
C21—C212	1.518 (6)	C211—H21B	0.9600
C31—C32	1.395 (5)	C211—H21C	0.9600
C31—C36	1.376 (7)	C212—H21D	0.9600
C32—C33	1.390 (9)	C212—H21E	0.9600
C33—C34	1.374 (7)	C212—H21F	0.9600
C1—N1—C3	110.1 (12)	N2—C2—H2B	109.00
C1—N1—C11	115.8 (9)	N3—C2—H2A	109.00
C3—N1—C11	117.4 (4)	N3—C2—H2B	109.00
C2—N2—C3	109.0 (7)	H2A—C2—H2B	108.00
C2—N2—C21	112.1 (12)	N1—C3—H3A	109.00
C3—N2—C21	114.9 (12)	N1—C3—H3B	109.00
C1—N3—C2	109.4 (12)	N2—C3—H3A	109.00
C1—N3—C31	116.1 (10)	N2—C3—H3B	109.00
C2—N3—C31	117.0 (5)	H3A—C3—H3B	108.00
N1—C1—N3	112.8 (6)	C11—C12—H12	119.00
N2—C2—N3	111.8 (12)	C13—C12—H12	119.00
N1—C3—N2	111.6 (12)	C12—C13—H13	120.00
N1—C11—C12	124.9 (5)	C14—C13—H13	120.00
N1—C11—C16	119.4 (3)	C13—C14—H14	120.00
C12—C11—C16	115.6 (6)	C15—C14—H14	120.00
C11—C12—C13	121.4 (6)	C14—C15—H15	121.00
C12—C13—C14	120.8 (3)	C16—C15—H15	121.00
C13—C14—C15	119.2 (6)	N2—C21—H21	106.00
C14—C15—C16	118.8 (6)	C211—C21—H21	106.00
F16—C16—C11	117.9 (6)	C212—C21—H21	106.00
F16—C16—C15	117.9 (7)	C31—C32—H32	120.00
C11—C16—C15	124.2 (3)	C33—C32—H32	120.00
N2—C21—C211	111.1 (9)	C32—C33—H33	119.00
N2—C21—C212	114.9 (4)	C34—C33—H33	119.00
C211—C21—C212	113.0 (10)	C33—C34—H34	120.00
N3—C31—C32	124.4 (4)	C35—C34—H34	120.00
N3—C31—C36	119.3 (3)	C34—C35—H35	120.00
C32—C31—C36	116.3 (6)	C36—C35—H35	120.00
C31—C32—C33	120.8 (4)	C21—C211—H21A	109.00
C32—C33—C34	121.1 (4)	C21—C211—H21B	109.00
C33—C34—C35	119.1 (6)	C21—C211—H21C	109.00
C34—C35—C36	119.3 (5)	H21A—C211—H21B	109.00
F36—C36—C31	118.7 (6)	H21A—C211—H21C	110.00
F36—C36—C35	117.9 (5)	H21B—C211—H21C	109.00
C31—C36—C35	123.4 (3)	C21—C212—H21D	110.00
N1—C1—H1A	109.00	C21—C212—H21E	109.00
N1—C1—H1B	109.00	C21—C212—H21F	109.00
N3—C1—H1A	109.00	H21D—C212—H21E	109.00
N3—C1—H1B	109.00	H21D—C212—H21F	109.00
H1A—C1—H1B	108.00	H21E—C212—H21F	109.00
N2—C2—H2A	109.00

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···CG1^i	0.97	2.71	3.493 (18)	138
C3—H3B···CG2^ii	0.97	2.87	3.608 (18)	134

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