Crystal structure of 2,4,6-tris­(cyclo­hex­yloxy)-1,3,5-triazine

The title compound, is the first tri-substituted cyclo­hex­yloxy triazine to be described. In the crystal, the triazine rings form (C3i-PU) Piedfort units and the mol­ecules are linked by C—H...O hydrogen bonds, forming ribbons propagating along [1-10].

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.142
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.608
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.92 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.61 eA-3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  O1      ..       2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  N1      ..       2.77 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C10    ..  O1      ..       3.79 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C21 H33 N3 O3
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.141 Check
PLAT975_ALERT_2_C Check Calcd Residual Density  1.03A From      N3       0.53 eA-3

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Degree

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: POV-RAY (POV-RAY Team, 2004) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015) and PLATON (Spek, 2009).

2,4,6-Tris(cyclohexyloxy)-1,3,5-triazine

Crystal data

C21H33N3O3	Z = 2
Mr = 375.50	F(000) = 408
Triclinic, P1	Dx = 1.244 Mg m^−3
a = 9.7020 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1456 (3) Å	Cell parameters from 9471 reflections
c = 11.2064 (3) Å	θ = 2.2–27.7°
α = 96.528 (2)°	µ = 0.08 mm^−1
β = 95.982 (2)°	T = 100 K
γ = 112.110 (2)°	Prism, colourless
V = 1002.30 (5) Å^3	0.47 × 0.24 × 0.10 mm

Data collection

Agilent SuperNova, Eos diffractometer	4106 independent reflections
Radiation source: Mo X-ray Source	3603 reflections with I > 2σ(I)
Detector resolution: 16.0965 pixels mm^-1	Rint = 0.027
ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (CrysAlis Pro; Agilent, 2014)	h = −12→12
Tmin = 0.657, Tmax = 1	k = −12→12
24791 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.7913P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4106 reflections	Δρmax = 0.61 e Å^−3
244 parameters	Δρmin = −0.21 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.24843 (18)	1.05014 (17)	0.49190 (14)	0.0195 (3)
C2	1.05411 (17)	0.83773 (16)	0.45059 (14)	0.0188 (3)
C3	1.07636 (18)	1.00085 (17)	0.32811 (14)	0.0194 (3)
C4	1.44642 (19)	1.10652 (17)	0.66284 (14)	0.0225 (4)
H4	1.4372	1.0047	0.6426	0.027*
C5	1.61162 (19)	1.20826 (19)	0.68357 (16)	0.0256 (4)
H5A	1.6204	1.3094	0.6976	0.031*
H5B	1.6569	1.1941	0.6105	0.031*
C6	1.6957 (2)	1.1792 (2)	0.79337 (17)	0.0295 (4)
H6A	1.6956	1.0813	0.7755	0.035*
H6B	1.8018	1.2495	0.8091	0.035*
C7	1.6240 (2)	1.19059 (19)	0.90564 (16)	0.0284 (4)
H7A	1.6353	1.2916	0.9295	0.034*
H7B	1.6765	1.1642	0.9737	0.034*
C8	1.4568 (2)	1.0913 (2)	0.88254 (16)	0.0277 (4)
H8A	1.4459	0.9896	0.8677	0.033*
H8B	1.4114	1.1055	0.9556	0.033*
C9	1.3732 (2)	1.1221 (2)	0.77312 (16)	0.0271 (4)
H9A	1.2663	1.0536	0.7574	0.033*
H9B	1.3763	1.2212	0.7902	0.033*
C10	0.83931 (18)	0.61278 (17)	0.40889 (15)	0.0220 (3)
H10	0.7850	0.6696	0.3740	0.026*
C11	0.7472 (2)	0.5209 (2)	0.49280 (16)	0.0293 (4)
H11A	0.7268	0.5829	0.5575	0.035*
H11B	0.8038	0.4697	0.5319	0.035*
C12	0.5979 (2)	0.4112 (2)	0.41799 (17)	0.0330 (4)
H12A	0.5375	0.3498	0.4718	0.040*
H12B	0.5395	0.4630	0.3826	0.040*
C13	0.6271 (2)	0.31714 (19)	0.31667 (17)	0.0317 (4)
H13A	0.5300	0.2477	0.2689	0.038*
H13B	0.6814	0.2618	0.3520	0.038*
C14	0.7213 (2)	0.4114 (2)	0.23329 (16)	0.0297 (4)
H14A	0.6643	0.4622	0.1941	0.036*
H14B	0.7422	0.3498	0.1685	0.036*
C15	0.87075 (19)	0.52219 (18)	0.30727 (15)	0.0243 (4)
H15A	0.9311	0.4715	0.3417	0.029*
H15B	0.9295	0.5851	0.2535	0.029*
C16	1.09447 (19)	1.17766 (17)	0.19788 (15)	0.0219 (3)
H16	1.1439	1.2490	0.2743	0.026*
C17	0.9714 (2)	1.2129 (2)	0.13237 (19)	0.0314 (4)
H17A	0.8992	1.2163	0.1877	0.038*
H17B	0.9159	1.1367	0.0612	0.038*
C18	1.0407 (2)	1.3590 (2)	0.09008 (19)	0.0338 (4)
H18A	0.9602	1.3788	0.0434	0.041*
H18B	1.0872	1.4361	0.1620	0.041*
C19	1.1586 (2)	1.36119 (19)	0.01149 (16)	0.0310 (4)
H19A	1.2046	1.4582	−0.0110	0.037*
H19B	1.1103	1.2906	−0.0643	0.037*
C20	1.2807 (2)	1.3241 (2)	0.07840 (19)	0.0350 (4)
H20A	1.3352	1.3995	0.1503	0.042*
H20B	1.3542	1.3216	0.0241	0.042*
C21	1.2106 (2)	1.17700 (19)	0.11921 (17)	0.0292 (4)
H21A	1.1629	1.1006	0.0469	0.035*
H21B	1.2903	1.1557	0.1653	0.035*
N1	1.18158 (15)	0.92270 (14)	0.52567 (12)	0.0202 (3)
N2	0.99553 (15)	0.86893 (14)	0.35006 (12)	0.0203 (3)
N3	1.20286 (15)	1.09706 (14)	0.39485 (12)	0.0208 (3)
O1	1.37668 (13)	1.14586 (12)	0.55837 (10)	0.0244 (3)
O2	0.98237 (13)	0.71122 (12)	0.48406 (10)	0.0227 (3)
O3	1.01921 (13)	1.03331 (12)	0.22770 (10)	0.0230 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0179 (7)	0.0191 (8)	0.0164 (7)	0.0030 (6)	0.0012 (6)	−0.0001 (6)
C2	0.0186 (7)	0.0166 (7)	0.0189 (7)	0.0042 (6)	0.0042 (6)	0.0024 (6)
C3	0.0224 (8)	0.0219 (8)	0.0154 (7)	0.0098 (6)	0.0041 (6)	0.0042 (6)
C4	0.0239 (8)	0.0199 (8)	0.0180 (8)	0.0039 (7)	−0.0038 (6)	0.0036 (6)
C5	0.0223 (8)	0.0265 (9)	0.0236 (8)	0.0046 (7)	0.0038 (7)	0.0047 (7)
C6	0.0204 (8)	0.0332 (10)	0.0304 (9)	0.0062 (7)	−0.0004 (7)	0.0063 (7)
C7	0.0308 (9)	0.0273 (9)	0.0211 (8)	0.0080 (7)	−0.0067 (7)	0.0020 (7)
C8	0.0290 (9)	0.0344 (10)	0.0206 (8)	0.0120 (8)	0.0051 (7)	0.0091 (7)
C9	0.0220 (8)	0.0340 (9)	0.0238 (9)	0.0089 (7)	0.0023 (7)	0.0075 (7)
C10	0.0201 (8)	0.0168 (8)	0.0218 (8)	0.0004 (6)	0.0006 (6)	0.0019 (6)
C11	0.0282 (9)	0.0278 (9)	0.0198 (8)	−0.0018 (7)	0.0013 (7)	0.0032 (7)
C12	0.0284 (9)	0.0279 (9)	0.0286 (9)	−0.0044 (7)	0.0026 (7)	0.0056 (7)
C13	0.0323 (10)	0.0191 (8)	0.0309 (9)	−0.0001 (7)	−0.0077 (8)	0.0008 (7)
C14	0.0334 (10)	0.0279 (9)	0.0226 (8)	0.0104 (8)	−0.0032 (7)	−0.0032 (7)
C15	0.0238 (8)	0.0244 (8)	0.0208 (8)	0.0066 (7)	0.0006 (6)	0.0014 (6)
C16	0.0260 (8)	0.0182 (8)	0.0186 (8)	0.0055 (6)	0.0007 (6)	0.0054 (6)
C17	0.0253 (9)	0.0287 (9)	0.0407 (11)	0.0093 (7)	0.0038 (8)	0.0138 (8)
C18	0.0337 (10)	0.0292 (10)	0.0416 (11)	0.0135 (8)	0.0046 (8)	0.0152 (8)
C19	0.0426 (11)	0.0223 (8)	0.0223 (8)	0.0061 (8)	0.0024 (8)	0.0076 (7)
C20	0.0330 (10)	0.0318 (10)	0.0415 (11)	0.0098 (8)	0.0145 (8)	0.0143 (8)
C21	0.0306 (9)	0.0261 (9)	0.0344 (10)	0.0122 (7)	0.0099 (8)	0.0110 (7)
N1	0.0195 (7)	0.0196 (7)	0.0167 (6)	0.0031 (5)	−0.0001 (5)	0.0030 (5)
N2	0.0191 (7)	0.0202 (7)	0.0177 (6)	0.0046 (5)	0.0003 (5)	0.0018 (5)
N3	0.0228 (7)	0.0183 (7)	0.0175 (7)	0.0041 (6)	0.0019 (5)	0.0038 (5)
O1	0.0228 (6)	0.0209 (6)	0.0204 (6)	−0.0001 (5)	−0.0041 (5)	0.0056 (5)
O2	0.0220 (6)	0.0188 (6)	0.0202 (6)	0.0009 (5)	−0.0012 (4)	0.0041 (4)
O3	0.0233 (6)	0.0203 (6)	0.0202 (6)	0.0037 (5)	−0.0025 (5)	0.0051 (4)

Geometric parameters (Å, º)

C1—N1	1.329 (2)	C11—H11A	0.9900
C1—O1	1.3338 (19)	C11—H11B	0.9900
C1—N3	1.334 (2)	C12—C13	1.518 (3)
C2—O2	1.3281 (19)	C12—H12A	0.9900
C2—N2	1.333 (2)	C12—H12B	0.9900
C2—N1	1.340 (2)	C13—C14	1.532 (3)
C3—N3	1.326 (2)	C13—H13A	0.9900
C3—O3	1.3318 (19)	C13—H13B	0.9900
C3—N2	1.339 (2)	C14—C15	1.537 (2)
C4—O1	1.4601 (19)	C14—H14A	0.9900
C4—C9	1.510 (2)	C14—H14B	0.9900
C4—C5	1.520 (2)	C15—H15A	0.9900
C4—H4	1.0000	C15—H15B	0.9900
C5—C6	1.524 (2)	C16—O3	1.4652 (19)
C5—H5A	0.9900	C16—C21	1.502 (2)
C5—H5B	0.9900	C16—C17	1.514 (2)
C6—C7	1.513 (3)	C16—H16	1.0000
C6—H6A	0.9900	C17—C18	1.533 (2)
C6—H6B	0.9900	C17—H17A	0.9900
C7—C8	1.529 (2)	C17—H17B	0.9900
C7—H7A	0.9900	C18—C19	1.510 (3)
C7—H7B	0.9900	C18—H18A	0.9900
C8—C9	1.526 (2)	C18—H18B	0.9900
C8—H8A	0.9900	C19—C20	1.524 (3)
C8—H8B	0.9900	C19—H19A	0.9900
C9—H9A	0.9900	C19—H19B	0.9900
C9—H9B	0.9900	C20—C21	1.535 (2)
C10—O2	1.4680 (18)	C20—H20A	0.9900
C10—C15	1.510 (2)	C20—H20B	0.9900
C10—C11	1.516 (2)	C21—H21A	0.9900
C10—H10	1.0000	C21—H21B	0.9900
C11—C12	1.536 (2)
N1—C1—O1	119.36 (14)	H12A—C12—H12B	108.1
N1—C1—N3	127.33 (14)	C12—C13—C14	109.90 (15)
O1—C1—N3	113.31 (14)	C12—C13—H13A	109.7
O2—C2—N2	119.16 (14)	C14—C13—H13A	109.7
O2—C2—N1	114.21 (14)	C12—C13—H13B	109.7
N2—C2—N1	126.63 (14)	C14—C13—H13B	109.7
N3—C3—O3	119.32 (14)	H13A—C13—H13B	108.2
N3—C3—N2	126.75 (14)	C13—C14—C15	110.08 (14)
O3—C3—N2	113.93 (14)	C13—C14—H14A	109.6
O1—C4—C9	111.01 (14)	C15—C14—H14A	109.6
O1—C4—C5	105.24 (13)	C13—C14—H14B	109.6
C9—C4—C5	111.64 (14)	C15—C14—H14B	109.6
O1—C4—H4	109.6	H14A—C14—H14B	108.2
C9—C4—H4	109.6	C10—C15—C14	109.76 (14)
C5—C4—H4	109.6	C10—C15—H15A	109.7
C4—C5—C6	109.90 (14)	C14—C15—H15A	109.7
C4—C5—H5A	109.7	C10—C15—H15B	109.7
C6—C5—H5A	109.7	C14—C15—H15B	109.7
C4—C5—H5B	109.7	H15A—C15—H15B	108.2
C6—C5—H5B	109.7	O3—C16—C21	109.68 (13)
H5A—C5—H5B	108.2	O3—C16—C17	105.89 (13)
C7—C6—C5	111.39 (15)	C21—C16—C17	111.75 (14)
C7—C6—H6A	109.3	O3—C16—H16	109.8
C5—C6—H6A	109.3	C21—C16—H16	109.8
C7—C6—H6B	109.3	C17—C16—H16	109.8
C5—C6—H6B	109.3	C16—C17—C18	109.82 (15)
H6A—C6—H6B	108.0	C16—C17—H17A	109.7
C6—C7—C8	111.16 (14)	C18—C17—H17A	109.7
C6—C7—H7A	109.4	C16—C17—H17B	109.7
C8—C7—H7A	109.4	C18—C17—H17B	109.7
C6—C7—H7B	109.4	H17A—C17—H17B	108.2
C8—C7—H7B	109.4	C19—C18—C17	111.37 (16)
H7A—C7—H7B	108.0	C19—C18—H18A	109.4
C9—C8—C7	111.15 (14)	C17—C18—H18A	109.4
C9—C8—H8A	109.4	C19—C18—H18B	109.4
C7—C8—H8A	109.4	C17—C18—H18B	109.4
C9—C8—H8B	109.4	H18A—C18—H18B	108.0
C7—C8—H8B	109.4	C18—C19—C20	110.83 (15)
H8A—C8—H8B	108.0	C18—C19—H19A	109.5
C4—C9—C8	109.41 (14)	C20—C19—H19A	109.5
C4—C9—H9A	109.8	C18—C19—H19B	109.5
C8—C9—H9A	109.8	C20—C19—H19B	109.5
C4—C9—H9B	109.8	H19A—C19—H19B	108.1
C8—C9—H9B	109.8	C19—C20—C21	110.28 (16)
H9A—C9—H9B	108.2	C19—C20—H20A	109.6
O2—C10—C15	109.31 (13)	C21—C20—H20A	109.6
O2—C10—C11	106.48 (13)	C19—C20—H20B	109.6
C15—C10—C11	111.73 (14)	C21—C20—H20B	109.6
O2—C10—H10	109.8	H20A—C20—H20B	108.1
C15—C10—H10	109.8	C16—C21—C20	110.14 (15)
C11—C10—H10	109.8	C16—C21—H21A	109.6
C10—C11—C12	108.91 (14)	C20—C21—H21A	109.6
C10—C11—H11A	109.9	C16—C21—H21B	109.6
C12—C11—H11A	109.9	C20—C21—H21B	109.6
C10—C11—H11B	109.9	H21A—C21—H21B	108.1
C12—C11—H11B	109.9	C1—N1—C2	112.84 (13)
H11A—C11—H11B	108.3	C2—N2—C3	113.31 (14)
C13—C12—C11	110.63 (16)	C3—N3—C1	113.12 (13)
C13—C12—H12A	109.5	C1—O1—C4	119.74 (12)
C11—C12—H12A	109.5	C2—O2—C10	117.91 (12)
C13—C12—H12B	109.5	C3—O3—C16	118.62 (12)
C11—C12—H12B	109.5
C4—O1—C1—N1	3.6 (2)	O1—C4—C5—C6	178.67 (14)
C4—O1—C1—N3	−175.80 (14)	C9—C4—C5—C6	58.2 (2)
C1—O1—C4—C5	157.44 (15)	O1—C4—C9—C8	−175.68 (14)
C1—O1—C4—C9	−81.64 (18)	C5—C4—C9—C8	−58.60 (19)
C2—O2—C10—C15	87.08 (17)	C4—C5—C6—C7	−55.8 (2)
C10—O2—C2—N1	178.32 (14)	C5—C6—C7—C8	55.0 (2)
C10—O2—C2—N2	−1.2 (2)	C6—C7—C8—C9	−55.5 (2)
C2—O2—C10—C11	−152.09 (15)	C7—C8—C9—C4	56.8 (2)
C3—O3—C16—C17	−148.75 (15)	O2—C10—C11—C12	−177.83 (14)
C16—O3—C3—N2	177.09 (15)	C11—C10—C15—C14	58.48 (19)
C16—O3—C3—N3	−3.1 (2)	C15—C10—C11—C12	−58.6 (2)
C3—O3—C16—C21	90.51 (18)	O2—C10—C15—C14	176.06 (13)
C2—N1—C1—O1	−179.98 (15)	C10—C11—C12—C13	58.4 (2)
C1—N1—C2—O2	−178.09 (15)	C11—C12—C13—C14	−58.9 (2)
C2—N1—C1—N3	−0.7 (3)	C12—C13—C14—C15	58.0 (2)
C1—N1—C2—N2	1.4 (3)	C13—C14—C15—C10	−57.36 (19)
C2—N2—C3—N3	0.1 (3)	O3—C16—C17—C18	−176.46 (14)
C3—N2—C2—O2	178.35 (15)	C21—C16—C17—C18	−57.1 (2)
C3—N2—C2—N1	−1.1 (3)	O3—C16—C21—C20	175.18 (14)
C2—N2—C3—O3	179.86 (14)	C17—C16—C21—C20	58.1 (2)
C1—N3—C3—O3	−179.28 (15)	C16—C17—C18—C19	55.9 (2)
C3—N3—C1—N1	−0.2 (3)	C17—C18—C19—C20	−56.4 (2)
C3—N3—C1—O1	179.16 (15)	C18—C19—C20—C21	56.6 (2)
C1—N3—C3—N2	0.5 (3)	C19—C20—C21—C16	−57.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1^i	0.99	2.45	3.413 (2)	164
C9—H9A···O3^ii	0.99	2.60	3.528 (2)	156
C10—H10···O1^ii	1.00	2.95	3.787 (2)	142
C5—H5B···N1^iii	0.99	2.77	3.684 (2)	154

Symmetry codes: (i) x−1, y−1, z; (ii) −x+2, −y+2, −z+1; (iii) −x+3, −y+2, −z+1.