Dianin's compound trichloro­acetonitrile clathrate

The the title compound [systematic name: 4-(2,2,4-trimethyl­chroman-4-yl)phenol–trichloro­acetonitrile (6/1)], 6C₁₈H₂₀O₂·C₂Cl₃N, the usual trigonal packing of the Dianin's compound host structure occurs. The guest is found in a host–guest ratio of 6:1. Cl...π inter­actions serve to order the guest, thus facilitating its structural characterization.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.144
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  Cl1    ..  C2      ..       3.08 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C2G
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      45.00 Perc.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED.

4-(2,2,4-trimethylchroman-4-yl)phenol–trichloroacetonitrile (6/1)

Crystal data

6C18H20O2·C2Cl3N	Dx = 1.291 Mg m^−3
Mr = 1754.42	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 4788 reflections
Hall symbol: -R 3	θ = 2.6–28.1°
a = 26.8141 (13) Å	µ = 0.17 mm^−1
c = 10.8765 (11) Å	T = 100 K
V = 6772.5 (8) Å^3	Prism, colourless
Z = 3	0.35 × 0.25 × 0.23 mm
F(000) = 2802

Data collection

Bruker APEX CCD area-detector diffractometer	2904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 28.3°, θmin = 1.5°
ω scans	h = −35→35
14334 measured reflections	k = −35→35
3553 independent reflections	l = −7→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.087P)^2 + 2.3737P] where P = (Fo^2 + 2Fc^2)/3
3553 reflections	(Δ/σ)max = 0.008
198 parameters	Δρmax = 0.57 e Å^−3
3 restraints	Δρmin = −0.45 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	Occ. (<1)
Cl1	0.06878 (4)	0.01762 (4)	0.29855 (10)	0.0309 (3)	0.50
O1	0.11967 (5)	0.06545 (6)	0.01537 (12)	0.0232 (3)
H1	0.1054	0.0867	0.0026	0.028*
C2	0.16123 (7)	0.08960 (7)	0.10582 (15)	0.0154 (3)
C3	0.18886 (7)	0.06009 (7)	0.14258 (15)	0.0153 (3)
H3	0.1801	0.0249	0.1038	0.018*
C4	0.22954 (7)	0.08226 (7)	0.23658 (15)	0.0141 (3)
H4	0.2480	0.0615	0.2613	0.017*
C5	0.24390 (7)	0.13377 (7)	0.29533 (14)	0.0126 (3)
C6	0.21608 (7)	0.16335 (7)	0.25456 (15)	0.0147 (3)
H6	0.2252	0.1989	0.2920	0.018*
C7	0.17558 (7)	0.14184 (7)	0.16099 (16)	0.0168 (4)
H7	0.1576	0.1628	0.1346	0.020*
C8	0.28780 (7)	0.15865 (6)	0.40194 (14)	0.0124 (3)
C9	0.26046 (7)	0.16606 (7)	0.52040 (15)	0.0135 (3)
H9A	0.2916	0.1952	0.5729	0.016*
H9B	0.2351	0.1815	0.4976	0.016*
C10	0.22552 (7)	0.11165 (7)	0.59634 (15)	0.0138 (3)
O11	0.26261 (5)	0.08818 (5)	0.62969 (11)	0.0156 (3)
C12	0.29876 (7)	0.08794 (7)	0.54117 (15)	0.0133 (3)
C13	0.31315 (6)	0.12039 (7)	0.43232 (15)	0.0129 (3)
C14	0.35323 (7)	0.11775 (7)	0.35403 (15)	0.0150 (3)
H14	0.3642	0.1399	0.2807	0.018*
C15	0.37740 (7)	0.08387 (7)	0.38004 (15)	0.0171 (4)
H15	0.4042	0.0826	0.3248	0.021*
C16	0.36209 (7)	0.05161 (7)	0.48823 (17)	0.0173 (4)
H16	0.3783	0.0281	0.5068	0.021*
C17	0.32341 (7)	0.05395 (7)	0.56823 (16)	0.0161 (4)
H17	0.3134	0.0323	0.6423	0.019*
C18	0.33648 (7)	0.21924 (7)	0.36509 (16)	0.0162 (3)
H18A	0.3200	0.2437	0.3456	0.024*
H18B	0.3567	0.2163	0.2928	0.024*
H18C	0.3637	0.2362	0.4335	0.024*
C19	0.20914 (8)	0.12718 (7)	0.71849 (15)	0.0179 (4)
H19A	0.2438	0.1575	0.7588	0.027*
H19B	0.1910	0.0930	0.7714	0.027*
H19C	0.1821	0.1410	0.7040	0.027*
C20	0.17244 (7)	0.06424 (7)	0.53195 (16)	0.0172 (4)
H20A	0.1838	0.0548	0.4537	0.026*
H20B	0.1450	0.0776	0.5165	0.026*
H20C	0.1544	0.0299	0.5843	0.026*
N1G	0.0000	0.0000	0.6047 (2)	0.104 (5)	0.50
C3G	0.0000	0.0000	0.36163 (14)	0.043 (3)	0.50
C2G	0.0000	0.0000	0.5000	0.0446 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0195 (4)	0.0383 (5)	0.0358 (6)	0.0150 (4)	0.0031 (4)	0.0046 (4)
O1	0.0191 (6)	0.0293 (7)	0.0194 (6)	0.0108 (5)	−0.0069 (5)	−0.0011 (5)
C2	0.0141 (8)	0.0194 (8)	0.0115 (8)	0.0074 (6)	0.0003 (6)	0.0010 (6)
C3	0.0165 (8)	0.0135 (7)	0.0143 (8)	0.0064 (6)	0.0018 (6)	0.0001 (6)
C4	0.0144 (7)	0.0142 (8)	0.0151 (8)	0.0083 (6)	0.0015 (6)	0.0017 (6)
C5	0.0115 (7)	0.0137 (7)	0.0119 (8)	0.0058 (6)	0.0019 (6)	0.0022 (6)
C6	0.0175 (8)	0.0146 (7)	0.0137 (8)	0.0093 (6)	0.0019 (6)	0.0001 (6)
C7	0.0177 (8)	0.0208 (8)	0.0168 (8)	0.0133 (7)	0.0006 (7)	0.0021 (7)
C8	0.0127 (7)	0.0123 (7)	0.0124 (8)	0.0064 (6)	0.0000 (6)	0.0000 (6)
C9	0.0140 (7)	0.0118 (7)	0.0146 (8)	0.0063 (6)	−0.0003 (6)	−0.0011 (6)
C10	0.0132 (7)	0.0147 (8)	0.0149 (8)	0.0081 (6)	0.0004 (6)	0.0008 (6)
O11	0.0160 (6)	0.0184 (6)	0.0153 (6)	0.0108 (5)	0.0027 (5)	0.0043 (5)
C12	0.0109 (7)	0.0122 (7)	0.0144 (8)	0.0039 (6)	−0.0018 (6)	−0.0023 (6)
C13	0.0119 (7)	0.0118 (7)	0.0144 (8)	0.0054 (6)	−0.0026 (6)	−0.0028 (6)
C14	0.0145 (8)	0.0152 (8)	0.0147 (8)	0.0071 (6)	−0.0011 (6)	−0.0015 (6)
C15	0.0154 (8)	0.0187 (8)	0.0188 (9)	0.0096 (7)	−0.0017 (6)	−0.0048 (7)
C16	0.0152 (8)	0.0144 (8)	0.0246 (9)	0.0093 (6)	−0.0054 (7)	−0.0034 (7)
C17	0.0156 (8)	0.0125 (7)	0.0183 (8)	0.0057 (6)	−0.0029 (6)	0.0013 (6)
C18	0.0150 (8)	0.0133 (7)	0.0190 (8)	0.0061 (6)	0.0018 (6)	0.0021 (6)
C19	0.0203 (8)	0.0187 (8)	0.0144 (8)	0.0096 (7)	0.0022 (7)	−0.0004 (6)
C20	0.0152 (8)	0.0154 (8)	0.0188 (8)	0.0061 (6)	0.0005 (6)	0.0005 (6)
N1G	0.084 (8)	0.084 (8)	0.144 (13)	0.042 (4)	0.000	0.000
C3G	0.015 (3)	0.015 (3)	0.101 (8)	0.0075 (14)	0.000	0.000
C2G	0.034 (2)	0.034 (2)	0.065 (5)	0.0171 (10)	0.000	0.000

Geometric parameters (Å, º)

Cl1—C3G	1.7954 (11)	O11—C12	1.3685 (19)
O1—C2	1.381 (2)	C12—C17	1.399 (2)
O1—H1	0.8400	C12—C13	1.404 (2)
C2—C3	1.386 (2)	C13—C14	1.400 (2)
C2—C7	1.390 (2)	C14—C15	1.384 (2)
C3—C4	1.393 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.395 (2)
C4—C5	1.390 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.379 (2)
C5—C6	1.405 (2)	C16—H16	0.9500
C5—C8	1.546 (2)	C17—H17	0.9500
C6—C7	1.386 (2)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—H7	0.9500	C18—H18C	0.9800
C8—C13	1.524 (2)	C19—H19A	0.9800
C8—C18	1.544 (2)	C19—H19B	0.9800
C8—C9	1.544 (2)	C19—H19C	0.9800
C9—C10	1.524 (2)	C20—H20A	0.9800
C9—H9A	0.9900	C20—H20B	0.9800
C9—H9B	0.9900	C20—H20C	0.9800
C10—O11	1.4639 (18)	N1G—C2G	1.139 (2)
C10—C19	1.521 (2)	C3G—C2G	1.5050 (16)
C10—C20	1.524 (2)
C2—O1—H1	109.5	O11—C12—C17	114.94 (14)
O1—C2—C3	118.31 (15)	O11—C12—C13	124.48 (14)
O1—C2—C7	122.14 (15)	C17—C12—C13	120.54 (15)
C3—C2—C7	119.55 (15)	C14—C13—C12	117.48 (14)
C2—C3—C4	119.75 (15)	C14—C13—C8	120.94 (14)
C2—C3—H3	120.1	C12—C13—C8	121.54 (14)
C4—C3—H3	120.1	C15—C14—C13	122.15 (15)
C5—C4—C3	122.01 (14)	C15—C14—H14	118.9
C5—C4—H4	119.0	C13—C14—H14	118.9
C3—C4—H4	119.0	C14—C15—C16	119.36 (15)
C4—C5—C6	117.02 (14)	C14—C15—H15	120.3
C4—C5—C8	123.12 (14)	C16—C15—H15	120.3
C6—C5—C8	119.85 (14)	C17—C16—C15	119.92 (15)
C7—C6—C5	121.57 (15)	C17—C16—H16	120.0
C7—C6—H6	119.2	C15—C16—H16	120.0
C5—C6—H6	119.2	C16—C17—C12	120.54 (16)
C6—C7—C2	120.06 (15)	C16—C17—H17	119.7
C6—C7—H7	120.0	C12—C17—H17	119.7
C2—C7—H7	120.0	C8—C18—H18A	109.5
C13—C8—C18	109.74 (13)	C8—C18—H18B	109.5
C13—C8—C9	107.83 (13)	H18A—C18—H18B	109.5
C18—C8—C9	106.70 (12)	C8—C18—H18C	109.5
C13—C8—C5	111.83 (12)	H18A—C18—H18C	109.5
C18—C8—C5	108.67 (13)	H18B—C18—H18C	109.5
C9—C8—C5	111.93 (12)	C10—C19—H19A	109.5
C10—C9—C8	115.69 (13)	C10—C19—H19B	109.5
C10—C9—H9A	108.4	H19A—C19—H19B	109.5
C8—C9—H9A	108.4	C10—C19—H19C	109.5
C10—C9—H9B	108.4	H19A—C19—H19C	109.5
C8—C9—H9B	108.4	H19B—C19—H19C	109.5
H9A—C9—H9B	107.4	C10—C20—H20A	109.5
O11—C10—C19	104.62 (13)	C10—C20—H20B	109.5
O11—C10—C9	108.74 (12)	H20A—C20—H20B	109.5
C19—C10—C9	109.56 (13)	C10—C20—H20C	109.5
O11—C10—C20	107.88 (13)	H20A—C20—H20C	109.5
C19—C10—C20	110.65 (13)	H20B—C20—H20C	109.5
C9—C10—C20	114.85 (13)	C2G—C3G—Cl1	112.46 (6)
C12—O11—C10	117.57 (12)	N1G—C2G—C3G	180.000 (1)
O1—C2—C3—C4	−177.75 (14)	C19—C10—O11—C12	−159.03 (13)
C7—C2—C3—C4	1.7 (2)	C9—C10—O11—C12	−42.04 (17)
C2—C3—C4—C5	−0.4 (2)	C20—C10—O11—C12	83.12 (16)
C3—C4—C5—C6	−0.9 (2)	C10—O11—C12—C17	−166.35 (13)
C3—C4—C5—C8	178.51 (14)	C10—O11—C12—C13	16.1 (2)
C4—C5—C6—C7	0.8 (2)	O11—C12—C13—C14	176.65 (14)
C8—C5—C6—C7	−178.63 (14)	C17—C12—C13—C14	−0.8 (2)
C5—C6—C7—C2	0.6 (2)	O11—C12—C13—C8	−1.4 (2)
O1—C2—C7—C6	177.63 (15)	C17—C12—C13—C8	−178.79 (14)
C3—C2—C7—C6	−1.8 (2)	C18—C8—C13—C14	−47.56 (19)
C4—C5—C8—C13	0.6 (2)	C9—C8—C13—C14	−163.42 (14)
C6—C5—C8—C13	−179.97 (14)	C5—C8—C13—C14	73.12 (18)
C4—C5—C8—C18	121.95 (16)	C18—C8—C13—C12	130.41 (15)
C6—C5—C8—C18	−58.67 (18)	C9—C8—C13—C12	14.56 (19)
C4—C5—C8—C9	−120.48 (16)	C5—C8—C13—C12	−108.91 (16)
C6—C5—C8—C9	58.91 (18)	C12—C13—C14—C15	1.2 (2)
C13—C8—C9—C10	−43.01 (17)	C8—C13—C14—C15	179.28 (14)
C18—C8—C9—C10	−160.85 (13)	C13—C14—C15—C16	−0.7 (2)
C5—C8—C9—C10	80.40 (17)	C14—C15—C16—C17	−0.3 (2)
C8—C9—C10—O11	57.67 (17)	C15—C16—C17—C12	0.8 (2)
C8—C9—C10—C19	171.46 (13)	O11—C12—C17—C16	−177.85 (14)
C8—C9—C10—C20	−63.29 (18)	C13—C12—C17—C16	−0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^i	0.84	1.98	2.803 (3)	166

Symmetry code: (i) x−y, x, −z.