Tris­(cyclo­hexyl­methyl)­amine

The title compound, C₂₁H₃₉N, is a sterically hindered amine with three cyclo­hexane rings, all having chair conformations. The bond angles at the N atom are 111.3 (2), 111.58 (19) and 110.3 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.065
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT049_ALERT_1_B Calculated Density less than 1.0 gcm-3 .........       1.00

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C31

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           25.31
           From the CIF: _reflns_number_total               2101
           Count of symmetry unique reflns         2118
           Completeness (_total/calc)             99.20%
           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
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I)

Crystal data

C21H39N	F(000) = 688
Mr = 305.53	Dx = 0.999 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10616 reflections
a = 11.050 (3) Å	θ = 3.1–25.3°
b = 11.2116 (4) Å	µ = 0.06 mm^−1
c = 16.3949 (6) Å	T = 291 K
V = 2031.2 (6) Å^3	Block, colourless
Z = 4	0.12 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.3°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −13→13
197 frames via ω–rotation (Δω=1°) and two times 30 s per frame (two sets at different κ–angles) scans	k = −13→13
2101 measured reflections	l = −19→19
2101 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0162P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max < 0.001
S = 0.88	Δρmax = 0.08 e Å^−3
2101 reflections	Δρmin = −0.08 e Å^−3
200 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0226 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map

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	0.2752 (2)	0.55534 (19)	0.14983 (12)	0.0657 (6)
C11	0.4071 (3)	0.3807 (3)	0.11635 (16)	0.0732 (8)
H11A	0.4270	0.4229	0.0657	0.088*
C12	0.3065 (3)	0.2948 (3)	0.09758 (18)	0.0884 (9)
H12A	0.2381	0.3388	0.0759	0.106*
H12B	0.2807	0.2568	0.1478	0.106*
C13	0.3428 (3)	0.1995 (3)	0.03696 (18)	0.1056 (11)
H13A	0.2763	0.1440	0.0297	0.127*
H13B	0.3596	0.2362	−0.0154	0.127*
C14	0.4526 (4)	0.1328 (3)	0.0653 (2)	0.1154 (12)
H14A	0.4769	0.0760	0.0238	0.139*
H14B	0.4332	0.0887	0.1145	0.139*
C15	0.5558 (3)	0.2176 (3)	0.0823 (2)	0.1187 (13)
H15A	0.5810	0.2550	0.0317	0.142*
H15B	0.6241	0.1731	0.1037	0.142*
C16	0.5199 (3)	0.3146 (3)	0.14374 (18)	0.0974 (11)
H16A	0.5053	0.2783	0.1965	0.117*
H16B	0.5861	0.3708	0.1497	0.117*
C17	0.3695 (3)	0.4736 (3)	0.17903 (15)	0.0790 (9)
H17A	0.3403	0.4331	0.2274	0.095*
H17B	0.4401	0.5199	0.1945	0.095*
C21	0.2423 (2)	0.7032 (2)	0.03774 (15)	0.0612 (8)
H21A	0.1655	0.7229	0.0645	0.073*
C22	0.2165 (2)	0.6131 (2)	−0.02790 (15)	0.0749 (9)
H22A	0.1801	0.5430	−0.0034	0.090*
H22B	0.2922	0.5889	−0.0529	0.090*
C23	0.1324 (3)	0.6613 (3)	−0.09346 (15)	0.0853 (10)
H23A	0.1225	0.6018	−0.1359	0.102*
H23B	0.0536	0.6771	−0.0699	0.102*
C24	0.1821 (3)	0.7749 (3)	−0.13043 (16)	0.0897 (10)
H24A	0.2562	0.7573	−0.1597	0.108*
H24B	0.1241	0.8070	−0.1690	0.108*
C25	0.2072 (3)	0.8660 (3)	−0.06500 (16)	0.0888 (10)
H25A	0.1316	0.8899	−0.0398	0.107*
H25B	0.2435	0.9362	−0.0895	0.107*
C26	0.2922 (3)	0.8166 (2)	0.00022 (15)	0.0752 (8)
H26A	0.3705	0.8002	−0.0240	0.090*
H26B	0.3034	0.8760	0.0426	0.090*
C27	0.3273 (2)	0.6535 (2)	0.10205 (15)	0.0709 (8)
H27A	0.4003	0.6254	0.0755	0.085*
H27B	0.3500	0.7173	0.1389	0.085*
C31	0.1026 (3)	0.5198 (2)	0.24604 (16)	0.0699 (8)
H31A	0.1392	0.4423	0.2586	0.084*
C32	0.0431 (3)	0.5667 (3)	0.32333 (16)	0.0922 (10)
H32A	0.1036	0.5731	0.3660	0.111*
H32B	0.0112	0.6459	0.3130	0.111*
C33	−0.0583 (4)	0.4866 (3)	0.35229 (19)	0.1144 (12)
H33A	−0.0252	0.4099	0.3683	0.137*
H33B	−0.0964	0.5219	0.3998	0.137*
C34	−0.1519 (3)	0.4683 (3)	0.2867 (2)	0.1131 (12)
H34A	−0.2129	0.4128	0.3058	0.136*
H34B	−0.1914	0.5436	0.2748	0.136*
C35	−0.0942 (3)	0.4203 (3)	0.2102 (2)	0.1004 (10)
H35A	−0.1549	0.4140	0.1677	0.120*
H35B	−0.0627	0.3410	0.2208	0.120*
C36	0.0085 (3)	0.5008 (3)	0.18090 (16)	0.0867 (10)
H36A	0.0463	0.4651	0.1334	0.104*
H36B	−0.0246	0.5773	0.1647	0.104*
C37	0.2022 (3)	0.6028 (2)	0.21770 (15)	0.0780 (9)
H37A	0.1661	0.6776	0.2007	0.094*
H37B	0.2553	0.6195	0.2634	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0711 (18)	0.0585 (16)	0.0675 (14)	−0.0008 (14)	0.0078 (13)	0.0070 (13)
C11	0.068 (2)	0.075 (2)	0.076 (2)	0.010 (2)	0.0033 (16)	0.0120 (18)
C12	0.080 (3)	0.076 (2)	0.110 (2)	0.017 (2)	−0.002 (2)	−0.005 (2)
C13	0.105 (3)	0.087 (3)	0.125 (3)	0.026 (2)	−0.007 (2)	−0.013 (2)
C14	0.110 (4)	0.099 (3)	0.138 (3)	0.035 (3)	0.011 (2)	−0.002 (2)
C15	0.083 (3)	0.132 (4)	0.141 (3)	0.042 (3)	0.015 (2)	0.016 (3)
C16	0.069 (3)	0.104 (3)	0.119 (3)	0.017 (2)	−0.0029 (19)	0.020 (2)
C17	0.084 (2)	0.079 (2)	0.0742 (19)	0.0019 (19)	−0.0086 (17)	0.015 (2)
C21	0.062 (2)	0.057 (2)	0.0643 (17)	0.0004 (16)	0.0043 (15)	0.0047 (16)
C22	0.082 (2)	0.068 (2)	0.0740 (18)	−0.0075 (19)	0.0061 (18)	−0.0043 (17)
C23	0.095 (3)	0.098 (3)	0.0627 (18)	−0.015 (2)	−0.0027 (19)	−0.0078 (19)
C24	0.091 (3)	0.108 (3)	0.070 (2)	0.001 (2)	0.0000 (19)	0.009 (2)
C25	0.101 (3)	0.083 (2)	0.083 (2)	0.001 (2)	0.0049 (19)	0.0181 (19)
C26	0.081 (2)	0.064 (2)	0.0804 (18)	−0.0085 (19)	−0.0002 (18)	0.0058 (16)
C27	0.068 (2)	0.064 (2)	0.0805 (18)	−0.0067 (17)	0.0011 (17)	0.0050 (17)
C31	0.082 (2)	0.058 (2)	0.0692 (19)	0.0072 (18)	0.0093 (17)	0.0092 (16)
C32	0.117 (3)	0.084 (2)	0.076 (2)	−0.004 (2)	0.0204 (19)	0.0047 (19)
C33	0.127 (4)	0.110 (3)	0.106 (3)	0.008 (3)	0.038 (3)	0.023 (2)
C34	0.095 (3)	0.096 (3)	0.148 (3)	0.007 (2)	0.041 (3)	0.027 (3)
C35	0.083 (3)	0.091 (3)	0.127 (3)	−0.006 (2)	0.006 (2)	0.009 (2)
C36	0.085 (3)	0.088 (3)	0.087 (2)	−0.003 (2)	0.012 (2)	0.0021 (19)
C37	0.097 (2)	0.069 (2)	0.0683 (17)	0.000 (2)	0.0092 (18)	−0.0028 (16)

Geometric parameters (Å, º)

N1—C17	1.468 (3)	C23—H23B	0.9700
N1—C27	1.468 (3)	C24—C25	1.508 (3)
N1—C37	1.474 (3)	C24—H24A	0.9700
C11—C12	1.503 (3)	C24—H24B	0.9700
C11—C16	1.518 (3)	C25—C26	1.527 (3)
C11—C17	1.521 (3)	C25—H25A	0.9700
C11—H11A	0.9800	C25—H25B	0.9700
C12—C13	1.513 (3)	C26—H26A	0.9700
C12—H12A	0.9700	C26—H26B	0.9700
C12—H12B	0.9700	C27—H27A	0.9700
C13—C14	1.498 (4)	C27—H27B	0.9700
C13—H13A	0.9700	C31—C36	1.506 (3)
C13—H13B	0.9700	C31—C37	1.514 (3)
C14—C15	1.511 (4)	C31—C32	1.521 (3)
C14—H14A	0.9700	C31—H31A	0.9800
C14—H14B	0.9700	C32—C33	1.513 (4)
C15—C16	1.534 (4)	C32—H32A	0.9700
C15—H15A	0.9700	C32—H32B	0.9700
C15—H15B	0.9700	C33—C34	1.506 (4)
C16—H16A	0.9700	C33—H33A	0.9700
C16—H16B	0.9700	C33—H33B	0.9700
C17—H17A	0.9700	C34—C35	1.505 (4)
C17—H17B	0.9700	C34—H34A	0.9700
C21—C22	1.503 (3)	C34—H34B	0.9700
C21—C26	1.516 (3)	C35—C36	1.527 (3)
C21—C27	1.518 (3)	C35—H35A	0.9700
C21—H21A	0.9800	C35—H35B	0.9700
C22—C23	1.520 (3)	C36—H36A	0.9700
C22—H22A	0.9700	C36—H36B	0.9700
C22—H22B	0.9700	C37—H37A	0.9700
C23—C24	1.513 (3)	C37—H37B	0.9700
C23—H23A	0.9700
C17—N1—C27	111.3 (2)	C23—C24—H24A	109.5
C17—N1—C37	111.58 (19)	C25—C24—H24B	109.5
C27—N1—C37	110.3 (2)	C23—C24—H24B	109.5
C12—C11—C16	110.8 (2)	H24A—C24—H24B	108.1
C12—C11—C17	112.1 (2)	C24—C25—C26	111.5 (2)
C16—C11—C17	111.0 (2)	C24—C25—H25A	109.3
C12—C11—H11A	107.6	C26—C25—H25A	109.3
C16—C11—H11A	107.6	C24—C25—H25B	109.3
C17—C11—H11A	107.6	C26—C25—H25B	109.3
C11—C12—C13	113.0 (3)	H25A—C25—H25B	108.0
C11—C12—H12A	109.0	C21—C26—C25	111.4 (2)
C13—C12—H12A	109.0	C21—C26—H26A	109.4
C11—C12—H12B	109.0	C25—C26—H26A	109.4
C13—C12—H12B	109.0	C21—C26—H26B	109.4
H12A—C12—H12B	107.8	C25—C26—H26B	109.4
C14—C13—C12	111.3 (3)	H26A—C26—H26B	108.0
C14—C13—H13A	109.4	N1—C27—C21	113.8 (2)
C12—C13—H13A	109.4	N1—C27—H27A	108.8
C14—C13—H13B	109.4	C21—C27—H27A	108.8
C12—C13—H13B	109.4	N1—C27—H27B	108.8
H13A—C13—H13B	108.0	C21—C27—H27B	108.8
C13—C14—C15	110.8 (3)	H27A—C27—H27B	107.7
C13—C14—H14A	109.5	C36—C31—C37	111.8 (2)
C15—C14—H14A	109.5	C36—C31—C32	109.9 (3)
C13—C14—H14B	109.5	C37—C31—C32	110.9 (2)
C15—C14—H14B	109.5	C36—C31—H31A	108.0
H14A—C14—H14B	108.1	C37—C31—H31A	108.0
C14—C15—C16	111.9 (3)	C32—C31—H31A	108.0
C14—C15—H15A	109.2	C33—C32—C31	112.1 (3)
C16—C15—H15A	109.2	C33—C32—H32A	109.2
C14—C15—H15B	109.2	C31—C32—H32A	109.2
C16—C15—H15B	109.2	C33—C32—H32B	109.2
H15A—C15—H15B	107.9	C31—C32—H32B	109.2
C11—C16—C15	111.3 (3)	H32A—C32—H32B	107.9
C11—C16—H16A	109.4	C34—C33—C32	111.4 (3)
C15—C16—H16A	109.4	C34—C33—H33A	109.3
C11—C16—H16B	109.4	C32—C33—H33A	109.3
C15—C16—H16B	109.4	C34—C33—H33B	109.3
H16A—C16—H16B	108.0	C32—C33—H33B	109.3
N1—C17—C11	113.6 (2)	H33A—C33—H33B	108.0
N1—C17—H17A	108.8	C35—C34—C33	110.7 (3)
C11—C17—H17A	108.8	C35—C34—H34A	109.5
N1—C17—H17B	108.8	C33—C34—H34A	109.5
C11—C17—H17B	108.8	C35—C34—H34B	109.5
H17A—C17—H17B	107.7	C33—C34—H34B	109.5
C22—C21—C26	110.0 (2)	H34A—C34—H34B	108.1
C22—C21—C27	111.5 (2)	C34—C35—C36	111.4 (3)
C26—C21—C27	111.4 (2)	C34—C35—H35A	109.3
C22—C21—H21A	107.9	C36—C35—H35A	109.3
C26—C21—H21A	107.9	C34—C35—H35B	109.3
C27—C21—H21A	107.9	C36—C35—H35B	109.3
C21—C22—C23	112.5 (2)	H35A—C35—H35B	108.0
C21—C22—H22A	109.1	C31—C36—C35	111.9 (2)
C23—C22—H22A	109.1	C31—C36—H36A	109.2
C21—C22—H22B	109.1	C35—C36—H36A	109.2
C23—C22—H22B	109.1	C31—C36—H36B	109.2
H22A—C22—H22B	107.8	C35—C36—H36B	109.2
C24—C23—C22	111.2 (2)	H36A—C36—H36B	107.9
C24—C23—H23A	109.4	N1—C37—C31	114.1 (2)
C22—C23—H23A	109.4	N1—C37—H37A	108.7
C24—C23—H23B	109.4	C31—C37—H37A	108.7
C22—C23—H23B	109.4	N1—C37—H37B	108.7
H23A—C23—H23B	108.0	C31—C37—H37B	108.7
C25—C24—C23	110.6 (2)	H37A—C37—H37B	107.6
C25—C24—H24A	109.5
C16—C11—C12—C13	−53.9 (3)	C27—C21—C26—C25	179.5 (2)
C17—C11—C12—C13	−178.5 (2)	C24—C25—C26—C21	−56.3 (3)
C11—C12—C13—C14	55.6 (3)	C17—N1—C27—C21	151.4 (2)
C12—C13—C14—C15	−55.4 (4)	C37—N1—C27—C21	−84.2 (3)
C13—C14—C15—C16	55.5 (4)	C22—C21—C27—N1	−66.1 (3)
C12—C11—C16—C15	52.8 (3)	C26—C21—C27—N1	170.5 (2)
C17—C11—C16—C15	177.9 (2)	C36—C31—C32—C33	54.8 (3)
C14—C15—C16—C11	−54.4 (4)	C37—C31—C32—C33	179.0 (3)
C27—N1—C17—C11	−83.3 (3)	C31—C32—C33—C34	−55.9 (4)
C37—N1—C17—C11	153.0 (2)	C32—C33—C34—C35	55.6 (4)
C12—C11—C17—N1	−66.2 (3)	C33—C34—C35—C36	−55.4 (4)
C16—C11—C17—N1	169.3 (2)	C37—C31—C36—C35	−178.2 (2)
C26—C21—C22—C23	−55.3 (3)	C32—C31—C36—C35	−54.5 (3)
C27—C21—C22—C23	−179.5 (2)	C34—C35—C36—C31	55.9 (4)
C21—C22—C23—C24	55.7 (3)	C17—N1—C37—C31	−82.0 (3)
C22—C23—C24—C25	−54.9 (3)	C27—N1—C37—C31	153.7 (2)
C23—C24—C25—C26	55.6 (3)	C36—C31—C37—N1	−64.9 (3)
C22—C21—C26—C25	55.3 (3)	C32—C31—C37—N1	172.0 (2)