O-[4-(2,2,4-Trimethyl­chroman-4-yl)phen­yl] N,N-dimethyl­thio­carbamate

The title compound, C₂₁H₂₆NO₂S, was obtained during the synthesis of the thiol derivative of Dianin's compound. Unlike Dianin's compound and the thiol derivatives, the title compound revealed no strong hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.071
• wR factor = 0.161
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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 (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED.

O-[4-(2,2,4-Trimethylchroman-4-yl)phenyl] N,N-dimethylthiocarbamate

Crystal data

C21H25NO2S	F(000) = 1520
Mr = 355.48	Dx = 1.253 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4336 reflections
a = 41.017 (8) Å	θ = 2.0–28.3°
b = 6.6341 (13) Å	µ = 0.19 mm^−1
c = 14.048 (3) Å	T = 100 K
β = 99.733 (3)°	Rectangular block, colourless
V = 3767.6 (13) Å^3	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection

Bruker APEX CCD area-detector diffractometer	4336 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −53→53
Tmin = 0.884, Tmax = 0.982	k = −8→8
10853 measured reflections	l = −13→18

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 8.1707P] where P = (Fo^2 + 2Fc^2)/3
4336 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.35 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
O1	0.20912 (4)	0.0148 (3)	0.31256 (14)	0.0204 (4)
C2	0.18842 (6)	−0.0830 (4)	0.37265 (19)	0.0181 (5)
C3	0.15433 (6)	−0.1178 (4)	0.31283 (19)	0.0167 (5)
H3B	0.1402	−0.1828	0.3545	0.020*
H3A	0.1566	−0.2137	0.2604	0.020*
C4	0.13644 (6)	0.0716 (4)	0.26741 (18)	0.0147 (5)
C5	0.15167 (6)	0.3690 (4)	0.16946 (18)	0.0173 (5)
H5	0.1287	0.3974	0.1523	0.021*
C6	0.17408 (7)	0.4885 (4)	0.13213 (18)	0.0199 (5)
H6	0.1666	0.5981	0.0906	0.024*
C7	0.20759 (7)	0.4471 (4)	0.15577 (19)	0.0205 (6)
H7	0.2232	0.5279	0.1301	0.025*
C8	0.21832 (6)	0.2886 (4)	0.21656 (19)	0.0206 (6)
H8	0.2413	0.2599	0.2325	0.025*
C9	0.19548 (6)	0.1701 (4)	0.25477 (18)	0.0170 (5)
C10	0.16170 (6)	0.2075 (4)	0.23166 (17)	0.0145 (5)
C11	0.11766 (6)	0.1767 (4)	0.33934 (18)	0.0144 (5)
C12	0.12415 (6)	0.3740 (4)	0.37115 (17)	0.0138 (5)
H12	0.1407	0.4492	0.3470	0.017*
C13	0.10707 (6)	0.4631 (4)	0.43722 (18)	0.0164 (5)
H13	0.1118	0.5976	0.4582	0.020*
C14	0.08307 (6)	0.3535 (4)	0.47196 (18)	0.0160 (5)
C15	0.07575 (6)	0.1584 (4)	0.44234 (18)	0.0167 (5)
H15	0.0591	0.0845	0.4668	0.020*
C16	0.09309 (6)	0.0717 (4)	0.37616 (18)	0.0166 (5)
H16	0.0881	−0.0627	0.3554	0.020*
O17	0.06792 (4)	0.4277 (3)	0.54755 (12)	0.0189 (4)
C18	0.04657 (6)	0.5859 (4)	0.53295 (18)	0.0143 (5)
S19	0.032450 (16)	0.68291 (10)	0.42437 (4)	0.01729 (17)
N20	0.03892 (5)	0.6459 (3)	0.61621 (15)	0.0171 (5)
C21	0.20513 (7)	−0.2827 (4)	0.3999 (2)	0.0228 (6)
H21A	0.2270	−0.2590	0.4384	0.034*
H21B	0.2075	−0.3571	0.3412	0.034*
H21C	0.1917	−0.3616	0.4378	0.034*
C22	0.18856 (7)	0.0475 (4)	0.46297 (19)	0.0236 (6)
H22A	0.1776	0.1763	0.4443	0.035*
H22B	0.2114	0.0722	0.4941	0.035*
H22C	0.1767	−0.0228	0.5081	0.035*
C23	0.11087 (6)	0.0008 (4)	0.17978 (19)	0.0198 (5)
H23A	0.0945	−0.0868	0.2022	0.030*
H23C	0.1222	−0.0739	0.1349	0.030*
H23B	0.0997	0.1184	0.1468	0.030*
C24	0.01602 (7)	0.8117 (4)	0.6208 (2)	0.0251 (6)
H24A	0.0157	0.8992	0.5645	0.038*
H24B	0.0232	0.8896	0.6799	0.038*
H24C	−0.0062	0.7579	0.6212	0.038*
C25	0.04846 (7)	0.5296 (4)	0.70528 (18)	0.0219 (6)
H25A	0.0340	0.4119	0.7043	0.033*
H25B	0.0464	0.6144	0.7610	0.033*
H25C	0.0714	0.4847	0.7101	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0171 (9)	0.0205 (10)	0.0243 (10)	0.0023 (7)	0.0054 (7)	0.0058 (8)
C2	0.0182 (12)	0.0193 (13)	0.0175 (12)	0.0026 (10)	0.0048 (10)	0.0011 (10)
C3	0.0191 (12)	0.0119 (12)	0.0199 (13)	0.0008 (10)	0.0057 (10)	−0.0008 (10)
C4	0.0161 (11)	0.0122 (12)	0.0156 (12)	0.0001 (9)	0.0020 (9)	−0.0021 (9)
C5	0.0178 (12)	0.0183 (13)	0.0160 (12)	0.0006 (10)	0.0039 (10)	−0.0018 (10)
C6	0.0294 (14)	0.0178 (13)	0.0131 (12)	−0.0007 (11)	0.0050 (10)	0.0005 (10)
C7	0.0248 (13)	0.0211 (14)	0.0172 (13)	−0.0056 (11)	0.0082 (10)	−0.0007 (10)
C8	0.0186 (12)	0.0214 (14)	0.0228 (13)	−0.0015 (11)	0.0060 (10)	−0.0035 (11)
C9	0.0194 (12)	0.0170 (13)	0.0146 (12)	0.0010 (10)	0.0031 (10)	−0.0022 (10)
C10	0.0187 (12)	0.0128 (12)	0.0126 (11)	−0.0017 (9)	0.0047 (9)	−0.0042 (9)
C11	0.0139 (11)	0.0142 (12)	0.0149 (12)	0.0028 (9)	0.0020 (9)	0.0007 (9)
C12	0.0147 (11)	0.0131 (12)	0.0137 (12)	−0.0010 (9)	0.0025 (9)	0.0013 (9)
C13	0.0197 (12)	0.0138 (12)	0.0152 (12)	0.0013 (10)	0.0016 (10)	−0.0008 (10)
C14	0.0185 (12)	0.0172 (13)	0.0131 (12)	0.0046 (10)	0.0047 (9)	0.0018 (9)
C15	0.0146 (11)	0.0184 (13)	0.0175 (12)	0.0004 (10)	0.0037 (9)	0.0042 (10)
C16	0.0180 (12)	0.0121 (12)	0.0194 (12)	−0.0005 (9)	0.0024 (10)	0.0011 (10)
O17	0.0250 (9)	0.0195 (10)	0.0133 (9)	0.0072 (8)	0.0066 (7)	0.0018 (7)
C18	0.0132 (11)	0.0127 (12)	0.0171 (12)	−0.0021 (9)	0.0028 (9)	−0.0009 (9)
S19	0.0216 (3)	0.0159 (3)	0.0142 (3)	0.0013 (2)	0.0025 (2)	0.0015 (2)
N20	0.0195 (10)	0.0171 (11)	0.0154 (10)	0.0015 (9)	0.0051 (8)	0.0007 (8)
C21	0.0244 (14)	0.0224 (15)	0.0225 (13)	0.0053 (11)	0.0062 (11)	0.0036 (11)
C22	0.0275 (14)	0.0235 (15)	0.0184 (13)	0.0035 (11)	−0.0001 (11)	−0.0021 (11)
C23	0.0208 (13)	0.0202 (13)	0.0183 (13)	−0.0022 (10)	0.0034 (10)	−0.0052 (11)
C24	0.0290 (15)	0.0234 (15)	0.0245 (14)	0.0046 (12)	0.0092 (11)	−0.0050 (11)
C25	0.0272 (14)	0.0284 (15)	0.0104 (12)	−0.0018 (12)	0.0045 (10)	−0.0001 (11)

Geometric parameters (Å, º)

O1—C9	1.372 (3)	C13—H13	0.9500
O1—C2	1.448 (3)	C14—C15	1.377 (4)
C2—C21	1.511 (4)	C14—O17	1.407 (3)
C2—C3	1.522 (4)	C15—C16	1.387 (4)
C2—C22	1.535 (4)	C15—H15	0.9500
C3—C4	1.538 (3)	C16—H16	0.9500
C3—H3B	0.9900	O17—C18	1.360 (3)
C3—H3A	0.9900	C18—N20	1.323 (3)
C4—C10	1.521 (3)	C18—S19	1.667 (3)
C4—C11	1.537 (3)	N20—C24	1.455 (3)
C4—C23	1.549 (3)	N20—C25	1.466 (3)
C5—C6	1.383 (4)	C21—H21A	0.9800
C5—C10	1.400 (4)	C21—H21B	0.9800
C5—H5	0.9500	C21—H21C	0.9800
C6—C7	1.386 (4)	C22—H22A	0.9800
C6—H6	0.9500	C22—H22B	0.9800
C7—C8	1.379 (4)	C22—H22C	0.9800
C7—H7	0.9500	C23—H23A	0.9800
C8—C9	1.398 (4)	C23—H23C	0.9800
C8—H8	0.9500	C23—H23B	0.9800
C9—C10	1.391 (3)	C24—H24A	0.9800
C11—C16	1.395 (3)	C24—H24B	0.9800
C11—C12	1.394 (3)	C24—H24C	0.9800
C12—C13	1.386 (3)	C25—H25A	0.9800
C12—H12	0.9500	C25—H25B	0.9800
C13—C14	1.378 (4)	C25—H25C	0.9800
C9—O1—C2	117.43 (19)	C15—C14—C13	121.4 (2)
O1—C2—C21	104.7 (2)	C15—C14—O17	117.1 (2)
O1—C2—C3	108.7 (2)	C13—C14—O17	121.0 (2)
C21—C2—C3	110.0 (2)	C14—C15—C16	118.8 (2)
O1—C2—C22	108.0 (2)	C14—C15—H15	120.6
C21—C2—C22	110.3 (2)	C16—C15—H15	120.6
C3—C2—C22	114.6 (2)	C15—C16—C11	121.7 (2)
C2—C3—C4	115.7 (2)	C15—C16—H16	119.1
C2—C3—H3B	108.3	C11—C16—H16	119.1
C4—C3—H3B	108.3	C18—O17—C14	120.78 (19)
C2—C3—H3A	108.3	N20—C18—O17	110.0 (2)
C4—C3—H3A	108.3	N20—C18—S19	126.5 (2)
H3B—C3—H3A	107.4	O17—C18—S19	123.46 (18)
C10—C4—C3	108.5 (2)	C18—N20—C24	121.2 (2)
C10—C4—C11	113.1 (2)	C18—N20—C25	121.8 (2)
C3—C4—C11	110.8 (2)	C24—N20—C25	116.2 (2)
C10—C4—C23	108.9 (2)	C2—C21—H21A	109.5
C3—C4—C23	107.1 (2)	C2—C21—H21B	109.5
C11—C4—C23	108.2 (2)	H21A—C21—H21B	109.5
C6—C5—C10	122.1 (2)	C2—C21—H21C	109.5
C6—C5—H5	118.9	H21A—C21—H21C	109.5
C10—C5—H5	118.9	H21B—C21—H21C	109.5
C5—C6—C7	119.4 (2)	C2—C22—H22A	109.5
C5—C6—H6	120.3	C2—C22—H22B	109.5
C7—C6—H6	120.3	H22A—C22—H22B	109.5
C8—C7—C6	120.0 (2)	C2—C22—H22C	109.5
C8—C7—H7	120.0	H22A—C22—H22C	109.5
C6—C7—H7	120.0	H22B—C22—H22C	109.5
C7—C8—C9	120.1 (2)	C4—C23—H23A	109.5
C7—C8—H8	119.9	C4—C23—H23C	109.5
C9—C8—H8	119.9	H23A—C23—H23C	109.5
O1—C9—C10	124.3 (2)	C4—C23—H23B	109.5
O1—C9—C8	114.6 (2)	H23A—C23—H23B	109.5
C10—C9—C8	121.1 (2)	H23C—C23—H23B	109.5
C9—C10—C5	117.3 (2)	N20—C24—H24A	109.5
C9—C10—C4	121.6 (2)	N20—C24—H24B	109.5
C5—C10—C4	121.0 (2)	H24A—C24—H24B	109.5
C16—C11—C12	117.4 (2)	N20—C24—H24C	109.5
C16—C11—C4	119.4 (2)	H24A—C24—H24C	109.5
C12—C11—C4	123.2 (2)	H24B—C24—H24C	109.5
C13—C12—C11	121.6 (2)	N20—C25—H25A	109.5
C13—C12—H12	119.2	N20—C25—H25B	109.5
C11—C12—H12	119.2	H25A—C25—H25B	109.5
C14—C13—C12	119.0 (2)	N20—C25—H25C	109.5
C14—C13—H13	120.5	H25A—C25—H25C	109.5
C12—C13—H13	120.5	H25B—C25—H25C	109.5
C9—O1—C2—C21	161.5 (2)	C11—C4—C10—C5	−70.3 (3)
C9—O1—C2—C3	44.0 (3)	C23—C4—C10—C5	50.1 (3)
C9—O1—C2—C22	−81.0 (3)	C10—C4—C11—C16	178.3 (2)
O1—C2—C3—C4	−57.3 (3)	C3—C4—C11—C16	−59.6 (3)
C21—C2—C3—C4	−171.4 (2)	C23—C4—C11—C16	57.5 (3)
C22—C2—C3—C4	63.6 (3)	C10—C4—C11—C12	−2.4 (3)
C2—C3—C4—C10	39.6 (3)	C3—C4—C11—C12	119.7 (3)
C2—C3—C4—C11	−85.2 (3)	C23—C4—C11—C12	−123.2 (3)
C2—C3—C4—C23	157.0 (2)	C16—C11—C12—C13	0.3 (4)
C10—C5—C6—C7	0.7 (4)	C4—C11—C12—C13	−179.0 (2)
C5—C6—C7—C8	−0.4 (4)	C11—C12—C13—C14	−0.1 (4)
C6—C7—C8—C9	−0.3 (4)	C12—C13—C14—C15	−0.1 (4)
C2—O1—C9—C10	−16.7 (3)	C12—C13—C14—O17	172.2 (2)
C2—O1—C9—C8	165.4 (2)	C13—C14—C15—C16	0.1 (4)
C7—C8—C9—O1	178.7 (2)	O17—C14—C15—C16	−172.5 (2)
C7—C8—C9—C10	0.8 (4)	C14—C15—C16—C11	0.2 (4)
O1—C9—C10—C5	−178.2 (2)	C12—C11—C16—C15	−0.4 (4)
C8—C9—C10—C5	−0.5 (4)	C4—C11—C16—C15	179.0 (2)
O1—C9—C10—C4	−1.8 (4)	C15—C14—O17—C18	−116.8 (3)
C8—C9—C10—C4	176.0 (2)	C13—C14—O17—C18	70.6 (3)
C6—C5—C10—C9	−0.3 (4)	C14—O17—C18—N20	−171.8 (2)
C6—C5—C10—C4	−176.7 (2)	C14—O17—C18—S19	8.9 (3)
C3—C4—C10—C9	−9.9 (3)	O17—C18—N20—C24	−179.1 (2)
C11—C4—C10—C9	113.4 (3)	S19—C18—N20—C24	0.2 (4)
C23—C4—C10—C9	−126.2 (2)	O17—C18—N20—C25	−9.5 (3)
C3—C4—C10—C5	166.4 (2)	S19—C18—N20—C25	169.8 (2)