Coupling of the lactone-ring conformation with crystal symmetry in 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Conformational disorder and inversions of the lactone ring induce structural transformations in the crystals of 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin, C₁₄H₁₈O₃. The onset of ordering of the lactone ring at 300 K proceeds continuously, changes the space group from P2₁/m to P2₁/c and doubles the unit cell; the abrupt inversion of the lactone rings at 225 K changes the crystal translational symmetry in the (010) plane. The mechanism combining the molecular conformation and dynamics with the crystal structure, its symmetry, and phase transitions is presented.

Computing details

For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(a308) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 645.3 (2) Å^3
Mr = 234.28	Z = 2
P21/m, monoclinic	F(000) = 252
a = 9.753 (2) Å	Dx = 1.206 Mg m^−3
b = 6.933 (1) Å	Cu Kα radiation, λ = 1.54178 Å
c = 9.572 (2) Å	µ = 0.68 mm^−1
α = 90°	T = 306 K
β = 94.39 (3)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 60.1°, θmin = 4.6°
1106 measured reflections	h = −10→10
1045 independent reflections	k = −7→0
864 reflections with I > 2σ(I)	l = 0→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.555P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 1.111
1045 reflections	Δρmax = 0.16 e Å^−3
157 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (2)

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)
O1	0.10337 (19)	0.2500	0.4954 (2)	0.0704 (8)
O2	−0.1147 (2)	0.2500	0.5232 (3)	0.1068 (12)
O6	0.6497 (2)	0.2500	0.6764 (3)	0.0645 (7)
H6	0.703 (5)	0.2500	0.607 (5)	0.122 (19)*
C2	−0.0006 (3)	0.2500	0.5743 (4)	0.0713 (11)
C3	0.0381 (5)	0.3542 (10)	0.7114 (5)	0.0729 (16)	0.50
H3A	−0.046 (5)	0.336 (7)	0.759 (5)	0.083 (16)*	0.50
H3B	0.073 (5)	0.513 (7)	0.696 (6)	0.064 (16)*	0.50
C4	0.1627 (3)	0.2500	0.7908 (4)	0.0685 (11)
C41	0.1953 (9)	0.3885 (18)	0.9212 (7)	0.121 (4)	0.50
H41A	0.2178	0.5175	0.8869	0.08 (9)*	0.25
H41B	0.2735	0.3426	0.9783	0.04 (2)*	0.25
H41C	0.1178	0.3998	0.9751	0.08 (3)*	0.25
H41D	0.1882	0.3224	1.0066	0.17 (7)*	0.25
H41E	0.1326	0.4974	0.9153	0.21 (16)*	0.25
H41F	0.2883	0.4402	0.9184	0.38 (19)*	0.25
C42	0.1284 (8)	0.0503 (16)	0.8300 (13)	0.117 (3)	0.50
H42A	0.0555	0.0555	0.8933	0.05 (2)*	0.25
H42B	0.2077	−0.0082	0.8775	0.05 (8)*	0.25
H42C	0.0986	−0.0203	0.7488	0.20 (18)*	0.25
H42D	0.1858	−0.0375	0.7864	2.0 (18)*	0.25
H42E	0.0335	0.0262	0.8022	0.13 (5)*	0.25
H42F	0.1426	0.0383	0.9310	0.15 (13)*	0.25
C5	0.4203 (3)	0.2500	0.7319 (3)	0.0467 (8)
C51	0.4810 (5)	0.2500	0.8820 (5)	0.0834 (14)
H51A	0.582 (8)	0.2500	0.878 (7)	0.22 (3)*
H51C	0.458 (4)	0.149 (6)	0.932 (4)	0.163 (18)*
C6	0.5129 (3)	0.2500	0.6283 (3)	0.0448 (8)
C7	0.4731 (3)	0.2500	0.4859 (3)	0.0430 (7)
C71	0.5798 (4)	0.2500	0.3803 (4)	0.0584 (10)
H71A	0.544 (4)	0.2500	0.286 (5)	0.102 (15)*
H71B	0.642 (3)	0.141 (4)	0.392 (3)	0.104 (10)*
C8	0.3331 (3)	0.2500	0.4446 (3)	0.0428 (7)
C81	0.2809 (4)	0.2500	0.2929 (4)	0.0597 (10)
H81A	0.192 (5)	0.2500	0.278 (5)	0.13 (2)*
H81C	0.306 (3)	0.139 (5)	0.238 (3)	0.125 (12)*
C9	0.2418 (3)	0.2500	0.5493 (3)	0.0435 (7)
C10	0.2789 (3)	0.2500	0.6912 (3)	0.0460 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0318 (11)	0.117 (2)	0.0628 (14)	0.000	0.0041 (10)	0.000
O2	0.0318 (14)	0.165 (3)	0.124 (3)	0.000	0.0091 (14)	0.000
O6	0.0358 (12)	0.0768 (17)	0.0793 (17)	0.000	−0.0063 (11)	0.000
C2	0.0360 (18)	0.100 (3)	0.079 (2)	0.000	0.0127 (17)	0.000
C3	0.048 (3)	0.104 (5)	0.070 (3)	0.019 (3)	0.025 (2)	0.003 (3)
C4	0.055 (2)	0.100 (3)	0.053 (2)	0.000	0.0196 (16)	0.000
C41	0.095 (5)	0.213 (11)	0.057 (4)	0.059 (6)	0.015 (4)	−0.030 (6)
C42	0.082 (5)	0.148 (8)	0.128 (7)	0.016 (5)	0.048 (5)	0.081 (8)
C5	0.0455 (16)	0.0479 (18)	0.0461 (17)	0.000	0.0005 (13)	0.000
C51	0.073 (3)	0.122 (4)	0.053 (2)	0.000	−0.0072 (19)	0.000
C6	0.0334 (15)	0.0403 (17)	0.0599 (18)	0.000	−0.0016 (12)	0.000
C7	0.0376 (16)	0.0371 (16)	0.0555 (18)	0.000	0.0105 (13)	0.000
C71	0.0453 (19)	0.063 (2)	0.070 (3)	0.000	0.0218 (17)	0.000
C8	0.0399 (15)	0.0424 (17)	0.0464 (16)	0.000	0.0061 (12)	0.000
C81	0.056 (2)	0.076 (3)	0.0467 (19)	0.000	0.0032 (15)	0.000
C9	0.0302 (14)	0.0503 (18)	0.0501 (17)	0.000	0.0037 (12)	0.000
C10	0.0438 (16)	0.0475 (18)	0.0475 (17)	0.000	0.0095 (13)	0.000

Geometric parameters (Å, º)

O1—C2	1.311 (4)	C41—H41F	0.977 (11)
O1—C9	1.409 (3)	C42—C41^i	1.131 (15)
O2—C2	1.180 (4)	C42—C3^i	1.534 (11)
O6—C6	1.378 (3)	C42—H42A	0.970 (7)
O6—H6	0.88 (5)	C42—H42B	0.957 (9)
C2—C3	1.520 (6)	C42—H42C	0.946 (16)
C2—C3^i	1.520 (6)	C42—H42D	0.945 (10)
C3—C3^i	1.445 (13)	C42—H42E	0.958 (11)
C3—C42^i	1.534 (11)	C42—H42F	0.969 (12)
C3—C4	1.561 (6)	C5—C6	1.391 (4)
C3—H3A	0.97 (5)	C5—C10	1.403 (4)
C3—H3B	1.16 (5)	C5—C51	1.512 (5)
C4—C42	1.480 (10)	C51—H51A	0.99 (8)
C4—C42^i	1.480 (10)	C51—H51C	0.88 (4)
C4—C10	1.536 (4)	C6—C7	1.388 (4)
C4—C3^i	1.561 (6)	C7—C8	1.392 (4)
C4—C41	1.587 (10)	C7—C71	1.505 (4)
C4—C41^i	1.587 (10)	C71—H71A	0.94 (4)
C41—C42^i	1.131 (15)	C71—H71B	0.97 (3)
C41—C41^i	1.92 (3)	C8—C9	1.390 (4)
C41—H41A	0.984 (13)	C8—C81	1.502 (4)
C41—H41B	0.958 (8)	C81—H81A	0.87 (5)
C41—H41C	0.951 (8)	C81—H81C	0.97 (3)
C41—H41D	0.945 (10)	C9—C10	1.379 (4)
C41—H41E	0.971 (10)
C2—O1—C9	123.4 (3)	C42^i—C41—H41F	108.8 (12)
C6—O6—H6	111 (3)	C4—C41—H41F	109.3 (5)
O2—C2—O1	120.5 (4)	C41^i—C41—H41F	111.5 (6)
O2—C2—C3	121.5 (3)	H41A—C41—H41F	55.0 (7)
O1—C2—C3	110.2 (3)	H41B—C41—H41F	55.8 (5)
O2—C2—C3^i	121.5 (3)	H41C—C41—H41F	139.7 (11)
O1—C2—C3^i	110.2 (3)	H41D—C41—H41F	109.3 (8)
C3—C2—C3^i	56.8 (5)	H41E—C41—H41F	107.2 (13)
C3^i—C3—C2	61.6 (3)	C41^i—C42—C4	73.5 (10)
C3^i—C3—C42^i	115.6 (6)	C41^i—C42—C3^i	132.3 (13)
C2—C3—C42^i	159.3 (4)	C4—C42—C3^i	62.4 (4)
C3^i—C3—C4	62.4 (3)	C41^i—C42—H42A	84.9 (12)
C2—C3—C4	109.5 (4)	C4—C42—H42A	108.3 (9)
C42^i—C3—C4	57.1 (5)	C3^i—C42—H42A	92.2 (6)
C3^i—C3—H3A	82 (3)	C41^i—C42—H42B	52.8 (9)
C2—C3—H3A	100 (3)	C4—C42—H42B	109.1 (10)
C42^i—C3—H3A	100 (3)	C3^i—C42—H42B	158.9 (8)
C4—C3—H3A	111 (3)	H42A—C42—H42B	108.9 (9)
C3^i—C3—H3B	161 (2)	C41^i—C42—H42C	162.1 (11)
C2—C3—H3B	113 (3)	C4—C42—H42C	109.7 (7)
C42^i—C3—H3B	62 (3)	C3^i—C42—H42C	59.4 (6)
C4—C3—H3B	106 (3)	H42A—C42—H42C	109.8 (11)
H3A—C3—H3B	117 (4)	H42B—C42—H42C	111.0 (11)
C42—C4—C42^i	138.7 (8)	C41^i—C42—H42D	104.9 (10)
C42—C4—C10	110.4 (4)	C4—C42—H42D	109.8 (5)
C42^i—C4—C10	110.4 (4)	C3^i—C42—H42D	106.1 (10)
C42—C4—C3^i	60.5 (6)	H42A—C42—H42D	141.9 (11)
C42^i—C4—C3^i	112.0 (5)	H42B—C42—H42D	56.8 (4)
C10—C4—C3^i	106.4 (3)	H42C—C42—H42D	57.2 (8)
C42—C4—C3	112.0 (5)	C41^i—C42—H42E	140.1 (13)
C42^i—C4—C3	60.5 (6)	C4—C42—H42E	109.0 (6)
C10—C4—C3	106.4 (3)	C3^i—C42—H42E	51.8 (5)
C3^i—C4—C3	55.1 (5)	H42A—C42—H42E	56.0 (4)
C42—C4—C41	113.7 (7)	H42B—C42—H42E	141.9 (10)
C42^i—C4—C41	43.1 (6)	H42C—C42—H42E	56.8 (8)
C10—C4—C41	112.0 (4)	H42D—C42—H42E	110.9 (16)
C3^i—C4—C41	139.8 (4)	C41^i—C42—H42F	39.9 (6)
C3—C4—C41	101.8 (4)	C4—C42—H42F	108.4 (12)
C42—C4—C41^i	43.1 (6)	C3^i—C42—H42F	143.6 (8)
C42^i—C4—C41^i	113.7 (7)	H42A—C42—H42F	55.6 (6)
C10—C4—C41^i	112.0 (4)	H42B—C42—H42F	56.1 (6)
C3^i—C4—C41^i	101.8 (4)	H42C—C42—H42F	141.9 (11)
C3—C4—C41^i	139.8 (4)	H42D—C42—H42F	110.0 (8)
C41—C4—C41^i	74.5 (9)	H42E—C42—H42F	108.9 (6)
C42^i—C41—C4	63.4 (6)	C6—C5—C10	118.7 (3)
C42^i—C41—C41^i	112.1 (9)	C6—C5—C51	116.7 (3)
C4—C41—C41^i	52.8 (4)	C10—C5—C51	124.7 (3)
C42^i—C41—H41A	62.1 (8)	C5—C51—H51A	106 (4)
C4—C41—H41A	108.9 (6)	C5—C51—H51C	114 (2)
C41^i—C41—H41A	155.5 (4)	H51A—C51—H51C	109 (3)
C42^i—C41—H41B	162.1 (11)	O6—C6—C7	121.2 (3)
C4—C41—H41B	110.5 (8)	O6—C6—C5	115.3 (3)
C41^i—C41—H41B	70.6 (8)	C7—C6—C5	123.5 (2)
H41A—C41—H41B	107.7 (11)	C6—C7—C8	118.2 (3)
C42^i—C41—H41C	87.3 (8)	C6—C7—C71	120.3 (3)
C4—C41—H41C	111.0 (9)	C8—C7—C71	121.5 (3)
C41^i—C41—H41C	94.7 (8)	C7—C71—H71A	114 (3)
H41A—C41—H41C	108.2 (10)	C7—C71—H71B	112.6 (17)
H41B—C41—H41C	110.4 (8)	H71A—C71—H71B	107 (2)
C42^i—C41—H41D	140.7 (12)	C9—C8—C7	117.6 (3)
C4—C41—H41D	111.4 (11)	C9—C8—C81	120.6 (3)
C41^i—C41—H41D	61.0 (7)	C7—C8—C81	121.8 (3)
H41A—C41—H41D	139.7 (10)	C8—C81—H81A	115 (3)
H41B—C41—H41D	56.8 (5)	C8—C81—H81C	115.9 (18)
H41C—C41—H41D	57.0 (5)	H81A—C81—H81C	102 (3)
C42^i—C41—H41E	48.7 (6)	C10—C9—C8	125.2 (2)
C4—C41—H41E	109.7 (7)	C10—C9—O1	122.2 (2)
C41^i—C41—H41E	141.1 (7)	C8—C9—O1	112.6 (2)
H41A—C41—H41E	55.2 (7)	C9—C10—C5	116.8 (3)
H41B—C41—H41E	139.6 (11)	C9—C10—C4	117.5 (3)
H41C—C41—H41E	56.2 (4)	C5—C10—C4	125.7 (3)
H41D—C41—H41E	109.9 (7)
C9—O1—C2—O2	180.0	C10—C4—C42—C3^i	−97.8 (4)
C9—O1—C2—C3	30.4 (3)	C3—C4—C42—C3^i	20.6 (5)
C9—O1—C2—C3^i	−30.4 (3)	C41—C4—C42—C3^i	135.3 (5)
O2—C2—C3—C3^i	109.3 (3)	C41^i—C4—C42—C3^i	161.4 (9)
O1—C2—C3—C3^i	−101.5 (2)	C10—C5—C6—O6	180.0
O2—C2—C3—C42^i	−163.0 (19)	C51—C5—C6—O6	0.0
O1—C2—C3—C42^i	−14 (2)	C10—C5—C6—C7	0.0
C3^i—C2—C3—C42^i	88 (2)	C51—C5—C6—C7	180.0
O2—C2—C3—C4	150.8 (3)	O6—C6—C7—C8	180.0
O1—C2—C3—C4	−60.0 (4)	C5—C6—C7—C8	0.0
C3^i—C2—C3—C4	41.5 (4)	O6—C6—C7—C71	0.0
C3^i—C3—C4—C42	−21.9 (5)	C5—C6—C7—C71	180.0
C2—C3—C4—C42	−63.0 (7)	C6—C7—C8—C9	0.0
C42^i—C3—C4—C42	134.7 (10)	C71—C7—C8—C9	180.0
C3^i—C3—C4—C42^i	−156.6 (5)	C6—C7—C8—C81	180.0
C2—C3—C4—C42^i	162.3 (6)	C71—C7—C8—C81	0.0
C3^i—C3—C4—C10	98.83 (18)	C7—C8—C9—C10	0.0
C2—C3—C4—C10	57.7 (4)	C81—C8—C9—C10	180.0
C42^i—C3—C4—C10	−104.6 (5)	C7—C8—C9—O1	180.0
C2—C3—C4—C3^i	−41.1 (4)	C81—C8—C9—O1	0.0
C42^i—C3—C4—C3^i	156.6 (5)	C2—O1—C9—C10	0.0
C3^i—C3—C4—C41	−143.7 (5)	C2—O1—C9—C8	180.0
C2—C3—C4—C41	175.1 (5)	C8—C9—C10—C5	0.0
C42^i—C3—C4—C41	12.9 (7)	O1—C9—C10—C5	180.0
C3^i—C3—C4—C41^i	−63.9 (7)	C8—C9—C10—C4	180.0
C2—C3—C4—C41^i	−105.1 (8)	O1—C9—C10—C4	0.0
C42^i—C3—C4—C41^i	92.7 (9)	C6—C5—C10—C9	0.0
C42—C4—C41—C42^i	−137.1 (8)	C51—C5—C10—C9	180.0
C10—C4—C41—C42^i	96.8 (6)	C6—C5—C10—C4	180.0
C3^i—C4—C41—C42^i	−65.3 (11)	C51—C5—C10—C4	0.0
C3—C4—C41—C42^i	−16.5 (8)	C42—C4—C10—C9	92.9 (6)
C41^i—C4—C41—C42^i	−155.3 (5)	C42^i—C4—C10—C9	−92.9 (6)
C42—C4—C41—C41^i	18.2 (4)	C3^i—C4—C10—C9	28.8 (3)
C42^i—C4—C41—C41^i	155.3 (5)	C3—C4—C10—C9	−28.8 (3)
C10—C4—C41—C41^i	−107.9 (4)	C41—C4—C10—C9	−139.3 (4)
C3^i—C4—C41—C41^i	90.0 (7)	C41^i—C4—C10—C9	139.3 (4)
C3—C4—C41—C41^i	138.8 (4)	C42—C4—C10—C5	−87.1 (6)
C42^i—C4—C42—C41^i	−71.0 (15)	C42^i—C4—C10—C5	87.1 (6)
C10—C4—C42—C41^i	100.8 (8)	C3^i—C4—C10—C5	−151.2 (3)
C3^i—C4—C42—C41^i	−161.4 (9)	C3—C4—C10—C5	151.2 (3)
C3—C4—C42—C41^i	−140.8 (7)	C41—C4—C10—C5	40.7 (4)
C41—C4—C42—C41^i	−26.1 (7)	C41^i—C4—C10—C5	−40.7 (4)
C42^i—C4—C42—C3^i	90.4 (15)

Symmetry code: (i) x, −y+1/2, z.

(a319) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 646.16 (13) Å^3
Mr = 234.28	Z = 2
P21/m, monoclinic	F(000) = 252
a = 9.753 (1) Å	Dx = 1.204 Mg m^−3
b = 6.941 (1) Å	Cu Kα radiation, λ = 1.54178 Å
c = 9.573 (1) Å	µ = 0.68 mm^−1
α = 90°	T = 317 K
β = 94.38 (1)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 57.5°, θmin = 4.6°
1035 measured reflections	h = −10→10
975 independent reflections	k = −7→0
804 reflections with I > 2σ(I)	l = 0→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0815P)^2 + 0.1245P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.407
975 reflections	Δρmax = 0.19 e Å^−3
164 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (5)

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)
O1	0.10325 (17)	0.2500	0.4956 (2)	0.0706 (7)
O2	−0.1145 (2)	0.2500	0.5232 (3)	0.1082 (11)
O6	0.64967 (18)	0.2500	0.6761 (2)	0.0645 (7)
H6	0.711 (4)	0.2500	0.609 (4)	0.102 (13)*
C2	−0.0004 (3)	0.2500	0.5741 (3)	0.0713 (10)
C3	0.0382 (4)	0.3550 (8)	0.7120 (5)	0.0736 (13)	0.50
H3A	−0.047 (5)	0.331 (6)	0.762 (5)	0.095 (16)*	0.50
H3B	0.069 (4)	0.507 (6)	0.699 (5)	0.063 (12)*	0.50
C4	0.1624 (3)	0.2500	0.7907 (3)	0.0684 (9)
C41	0.1955 (8)	0.3891 (15)	0.9212 (6)	0.120 (3)	0.50
H41A	0.2178	0.5171	0.8874	0.08 (9)*	0.25
H41B	0.2735	0.3421	0.9784	0.040 (17)*	0.25
H41C	0.1178	0.3993	0.9754	0.06 (2)*	0.25
H41D	0.1882	0.3219	1.0068	0.14 (5)*	0.25
H41E	0.1326	0.4969	0.9157	0.27 (16)*	0.25
H41F	0.2883	0.4397	0.9187	0.38 (18)*	0.25
C42	0.1270 (6)	0.0495 (13)	0.8282 (10)	0.116 (3)	0.50
H42A	0.0552	0.0551	0.8925	0.034 (15)*	0.25
H42B	0.2075	−0.0084	0.8767	0.07 (8)*	0.25
H42C	0.0986	−0.0199	0.7478	0.4 (2)*	0.25
H42D	0.1856	−0.0372	0.7855	2 (2)*	0.25
H42E	0.0333	0.0263	0.8013	0.10 (4)*	0.25
H42F	0.1423	0.0377	0.9302	0.09 (4)*	0.25
C5	0.4203 (2)	0.2500	0.7319 (3)	0.0478 (7)
C51	0.4816 (4)	0.2500	0.8819 (4)	0.0834 (12)
H51A	0.578 (7)	0.2500	0.870 (6)	0.19 (3)*
H51C	0.448 (3)	0.153 (5)	0.933 (3)	0.147 (14)*
C6	0.5132 (2)	0.2500	0.6289 (3)	0.0444 (7)
C7	0.4731 (2)	0.2500	0.4857 (3)	0.0438 (7)
C71	0.5796 (3)	0.2500	0.3804 (4)	0.0579 (8)
H71A	0.541 (4)	0.2500	0.288 (5)	0.111 (14)*
H71B	0.642 (3)	0.146 (4)	0.394 (2)	0.098 (8)*
C8	0.3329 (2)	0.2500	0.4446 (2)	0.0434 (7)
C81	0.2807 (3)	0.2500	0.2932 (3)	0.0595 (9)
H81A	0.176 (7)	0.2500	0.293 (6)	0.057 (16)*	0.50
H81C	0.314 (4)	0.128 (6)	0.240 (4)	0.050 (9)*	0.50
H81D	0.351 (10)	0.2500	0.222 (9)	0.12 (3)*	0.50
H81E	0.217 (4)	0.142 (7)	0.266 (4)	0.061 (11)*	0.50
C9	0.2418 (2)	0.2500	0.5487 (3)	0.0438 (7)
C10	0.2790 (2)	0.2500	0.6918 (2)	0.0462 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0314 (10)	0.1178 (19)	0.0626 (12)	0.000	0.0039 (8)	0.000
O2	0.0335 (13)	0.167 (3)	0.124 (2)	0.000	0.0099 (12)	0.000
O6	0.0357 (11)	0.0765 (14)	0.0795 (14)	0.000	−0.0070 (9)	0.000
C2	0.0321 (16)	0.101 (2)	0.082 (2)	0.000	0.0116 (14)	0.000
C3	0.048 (2)	0.103 (4)	0.072 (3)	0.018 (2)	0.0239 (19)	0.002 (3)
C4	0.0557 (18)	0.097 (2)	0.0552 (17)	0.000	0.0202 (13)	0.000
C41	0.095 (4)	0.211 (9)	0.055 (3)	0.061 (5)	0.016 (3)	−0.029 (4)
C42	0.075 (4)	0.149 (6)	0.130 (6)	0.013 (4)	0.047 (4)	0.082 (6)
C5	0.0477 (15)	0.0452 (15)	0.0498 (14)	0.000	−0.0006 (11)	0.000
C51	0.073 (2)	0.121 (3)	0.0538 (18)	0.000	−0.0077 (16)	0.000
C6	0.0311 (13)	0.0400 (14)	0.0614 (15)	0.000	−0.0018 (10)	0.000
C7	0.0371 (13)	0.0369 (14)	0.0581 (15)	0.000	0.0084 (11)	0.000
C71	0.0447 (16)	0.061 (2)	0.071 (2)	0.000	0.0211 (14)	0.000
C8	0.0397 (14)	0.0419 (14)	0.0491 (14)	0.000	0.0070 (10)	0.000
C81	0.0531 (18)	0.075 (2)	0.0497 (16)	0.000	0.0007 (13)	0.000
C9	0.0293 (12)	0.0509 (15)	0.0512 (14)	0.000	0.0030 (10)	0.000
C10	0.0415 (14)	0.0486 (15)	0.0492 (14)	0.000	0.0084 (11)	0.000

Geometric parameters (Å, º)

O1—C2	1.305 (3)	C42—C41^i	1.153 (11)
O1—C9	1.407 (3)	C42—C3^i	1.510 (9)
O2—C2	1.180 (4)	C42—H42A	0.968 (6)
O6—C6	1.373 (3)	C42—H42B	0.968 (7)
O6—H6	0.92 (4)	C42—H42C	0.932 (12)
C2—C3	1.530 (6)	C42—H42D	0.944 (8)
C2—C3^i	1.530 (6)	C42—H42E	0.944 (8)
C3—C3^i	1.458 (12)	C42—H42F	0.980 (9)
C3—C42^i	1.510 (9)	C5—C6	1.389 (4)
C3—C4	1.558 (5)	C5—C10	1.403 (3)
C3—H3A	1.01 (5)	C5—C51	1.513 (4)
C3—H3B	1.11 (4)	C51—H51A	0.96 (7)
C4—C42^i	1.485 (8)	C51—H51C	0.91 (3)
C4—C42	1.485 (8)	C6—C7	1.396 (4)
C4—C10	1.534 (3)	C7—C8	1.393 (3)
C4—C3^i	1.558 (5)	C7—C71	1.503 (3)
C4—C41	1.593 (8)	C71—H71A	0.93 (4)
C4—C41^i	1.593 (8)	C71—H71B	0.95 (3)
C41—C42^i	1.153 (11)	C8—C9	1.384 (3)
C41—C41^i	1.93 (2)	C8—C81	1.499 (4)
C41—H41A	0.976 (11)	C81—H81A	1.02 (6)
C41—H41B	0.959 (7)	C81—H81C	1.05 (4)
C41—H41C	0.954 (6)	C81—H81D	1.00 (9)
C41—H41D	0.950 (8)	C81—H81E	0.99 (4)
C41—H41E	0.966 (8)	C9—C10	1.391 (3)
C41—H41F	0.972 (9)
C2—O1—C9	123.9 (2)	H41A—C41—H41F	55.4 (6)
C6—O6—H6	116 (3)	H41B—C41—H41F	55.9 (4)
O2—C2—O1	120.7 (3)	H41C—C41—H41F	140.1 (9)
O2—C2—C3	121.2 (2)	H41D—C41—H41F	109.3 (7)
O1—C2—C3	110.3 (2)	H41E—C41—H41F	107.9 (10)
O2—C2—C3^i	121.2 (2)	C41^i—C42—C4	73.1 (8)
O1—C2—C3^i	110.3 (2)	C41^i—C42—C3^i	132.3 (10)
C3—C2—C3^i	56.9 (4)	C4—C42—C3^i	62.7 (3)
C3^i—C3—C42^i	116.0 (5)	C41^i—C42—H42A	84.2 (9)
C3^i—C3—C2	61.5 (2)	C4—C42—H42A	108.0 (7)
C42^i—C3—C2	159.1 (3)	C3^i—C42—H42A	92.8 (5)
C3^i—C3—C4	62.1 (2)	C41^i—C42—H42B	51.9 (7)
C42^i—C3—C4	57.9 (4)	C4—C42—H42B	108.1 (7)
C2—C3—C4	109.0 (3)	C3^i—C42—H42B	159.1 (6)
C3^i—C3—H3A	80 (3)	H42A—C42—H42B	108.1 (7)
C42^i—C3—H3A	100 (3)	C41^i—C42—H42C	161.3 (9)
C2—C3—H3A	100 (3)	C4—C42—H42C	110.2 (5)
C4—C3—H3A	110 (3)	C3^i—C42—H42C	60.0 (5)
C3^i—C3—H3B	162.4 (19)	H42A—C42—H42C	111.2 (8)
C42^i—C3—H3B	61 (2)	H42B—C42—H42C	111.2 (9)
C2—C3—H3B	114 (2)	C41^i—C42—H42D	103.6 (8)
C4—C3—H3B	107 (2)	C4—C42—H42D	109.5 (4)
H3A—C3—H3B	117 (3)	C3^i—C42—H42D	107.1 (8)
C42^i—C4—C42	139.3 (6)	H42A—C42—H42D	142.4 (8)
C42^i—C4—C10	110.2 (3)	H42B—C42—H42D	56.5 (3)
C42—C4—C10	110.2 (3)	H42C—C42—H42D	57.7 (6)
C42^i—C4—C3^i	111.7 (4)	C41^i—C42—H42E	139.9 (10)
C42—C4—C3^i	59.5 (4)	C4—C42—H42E	109.4 (5)
C10—C4—C3^i	106.7 (2)	C3^i—C42—H42E	52.0 (4)
C42^i—C4—C3	59.5 (4)	H42A—C42—H42E	56.5 (3)
C42—C4—C3	111.7 (4)	H42B—C42—H42E	142.4 (8)
C10—C4—C3	106.7 (2)	H42C—C42—H42E	57.7 (6)
C3^i—C4—C3	55.8 (4)	H42D—C42—H42E	112.3 (12)
C42^i—C4—C41	43.8 (5)	C41^i—C42—H42F	39.3 (5)
C42—C4—C41	114.6 (6)	C4—C42—H42F	107.4 (9)
C10—C4—C41	111.6 (3)	C3^i—C42—H42F	143.6 (7)
C3^i—C4—C41	140.0 (4)	H42A—C42—H42F	55.4 (4)
C3—C4—C41	101.5 (3)	H42B—C42—H42F	55.3 (5)
C42^i—C4—C41^i	114.6 (6)	H42C—C42—H42F	142.5 (8)
C42—C4—C41^i	43.8 (5)	H42D—C42—H42F	109.1 (6)
C10—C4—C41^i	111.6 (3)	H42E—C42—H42F	109.1 (5)
C3^i—C4—C41^i	101.5 (3)	C6—C5—C10	119.1 (2)
C3—C4—C41^i	140.0 (4)	C6—C5—C51	116.2 (3)
C41—C4—C41^i	74.6 (7)	C10—C5—C51	124.6 (3)
C42^i—C41—C4	63.1 (5)	C5—C51—H51A	102 (4)
C42^i—C41—C41^i	111.7 (7)	C5—C51—H51C	112 (2)
C4—C41—C41^i	52.7 (3)	H51A—C51—H51C	118 (3)
C42^i—C41—H41A	62.5 (6)	O6—C6—C5	115.8 (2)
C4—C41—H41A	109.1 (4)	O6—C6—C7	121.0 (2)
C41^i—C41—H41A	155.5 (3)	C5—C6—C7	123.2 (2)
C42^i—C41—H41B	162.4 (8)	C8—C7—C6	118.2 (2)
C4—C41—H41B	110.2 (6)	C8—C7—C71	121.6 (2)
C41^i—C41—H41B	70.1 (6)	C6—C7—C71	120.2 (2)
H41A—C41—H41B	108.2 (9)	C7—C71—H71A	113 (3)
C42^i—C41—H41C	87.4 (6)	C7—C71—H71B	111.8 (15)
C4—C41—H41C	110.5 (8)	H71A—C71—H71B	110 (2)
C41^i—C41—H41C	94.2 (6)	C9—C8—C7	117.8 (2)
H41A—C41—H41C	108.7 (8)	C9—C8—C81	120.4 (2)
H41B—C41—H41C	110.1 (6)	C7—C8—C81	121.8 (2)
C42^i—C41—H41D	140.4 (10)	C8—C81—H81A	106 (3)
C4—C41—H41D	110.7 (9)	C8—C81—H81C	112 (2)
C41^i—C41—H41D	60.6 (5)	H81A—C81—H81C	110 (3)
H41A—C41—H41D	140.1 (8)	C8—C81—H81D	117 (5)
H41B—C41—H41D	56.6 (4)	H81A—C81—H81D	137 (6)
H41C—C41—H41D	56.8 (4)	H81C—C81—H81D	55 (2)
C42^i—C41—H41E	49.0 (4)	C8—C81—H81E	114 (2)
C4—C41—H41E	109.7 (5)	H81A—C81—H81E	53 (2)
C41^i—C41—H41E	140.7 (6)	H81C—C81—H81E	59 (3)
H41A—C41—H41E	55.6 (5)	H81D—C81—H81E	106 (4)
H41B—C41—H41E	140.1 (9)	C8—C9—C10	125.2 (2)
H41C—C41—H41E	56.2 (3)	C8—C9—O1	113.1 (2)
H41D—C41—H41E	109.8 (5)	C10—C9—O1	121.8 (2)
C42^i—C41—H41F	109.4 (9)	C9—C10—C5	116.5 (2)
C4—C41—H41F	109.4 (4)	C9—C10—C4	117.3 (2)
C41^i—C41—H41F	111.1 (5)	C5—C10—C4	126.2 (2)
C9—O1—C2—O2	180.0	C10—C4—C42—C3^i	−97.9 (3)
C9—O1—C2—C3	30.5 (2)	C3—C4—C42—C3^i	20.5 (4)
C9—O1—C2—C3^i	−30.5 (2)	C41—C4—C42—C3^i	135.1 (4)
O2—C2—C3—C3^i	109.2 (3)	C41^i—C4—C42—C3^i	161.5 (7)
O1—C2—C3—C3^i	−101.54 (17)	C10—C5—C6—O6	180.0
O2—C2—C3—C42^i	−162.0 (15)	C51—C5—C6—O6	0.0
O1—C2—C3—C42^i	−12.7 (17)	C10—C5—C6—C7	0.0
C3^i—C2—C3—C42^i	88.9 (16)	C51—C5—C6—C7	180.0
O2—C2—C3—C4	150.6 (2)	O6—C6—C7—C8	180.0
O1—C2—C3—C4	−60.1 (3)	C5—C6—C7—C8	0.0
C3^i—C2—C3—C4	41.5 (3)	O6—C6—C7—C71	0.0
C3^i—C3—C4—C42^i	−156.8 (4)	C5—C6—C7—C71	180.0
C2—C3—C4—C42^i	162.0 (5)	C6—C7—C8—C9	0.0
C3^i—C3—C4—C42	−21.4 (4)	C71—C7—C8—C9	180.0
C42^i—C3—C4—C42	135.4 (8)	C6—C7—C8—C81	180.0
C2—C3—C4—C42	−62.6 (5)	C71—C7—C8—C81	0.0
C3^i—C3—C4—C10	99.14 (16)	C7—C8—C9—C10	0.0
C42^i—C3—C4—C10	−104.0 (4)	C81—C8—C9—C10	180.0
C2—C3—C4—C10	57.9 (3)	C7—C8—C9—O1	180.0
C42^i—C3—C4—C3^i	156.8 (4)	C81—C8—C9—O1	0.0
C2—C3—C4—C3^i	−41.2 (3)	C2—O1—C9—C8	180.0
C3^i—C3—C4—C41	−143.9 (4)	C2—O1—C9—C10	0.0
C42^i—C3—C4—C41	13.0 (6)	C8—C9—C10—C5	0.0
C2—C3—C4—C41	174.9 (4)	O1—C9—C10—C5	180.0
C3^i—C3—C4—C41^i	−64.1 (6)	C8—C9—C10—C4	180.0
C42^i—C3—C4—C41^i	92.7 (7)	O1—C9—C10—C4	0.0
C2—C3—C4—C41^i	−105.3 (6)	C6—C5—C10—C9	0.0
C42—C4—C41—C42^i	−136.6 (7)	C51—C5—C10—C9	180.0
C10—C4—C41—C42^i	97.1 (5)	C6—C5—C10—C4	180.0
C3^i—C4—C41—C42^i	−65.6 (9)	C51—C5—C10—C4	0.0
C3—C4—C41—C42^i	−16.2 (6)	C42^i—C4—C10—C9	−92.2 (5)
C41^i—C4—C41—C42^i	−155.2 (4)	C42—C4—C10—C9	92.2 (5)
C42^i—C4—C41—C41^i	155.2 (4)	C3^i—C4—C10—C9	29.2 (2)
C42—C4—C41—C41^i	18.6 (3)	C3—C4—C10—C9	−29.2 (2)
C10—C4—C41—C41^i	−107.6 (3)	C41—C4—C10—C9	−139.3 (3)
C3^i—C4—C41—C41^i	89.7 (6)	C41^i—C4—C10—C9	139.3 (3)
C3—C4—C41—C41^i	139.1 (3)	C42^i—C4—C10—C5	87.8 (5)
C42^i—C4—C42—C41^i	−73.2 (11)	C42—C4—C10—C5	−87.8 (5)
C10—C4—C42—C41^i	100.6 (7)	C3^i—C4—C10—C5	−150.8 (2)
C3^i—C4—C42—C41^i	−161.5 (7)	C3—C4—C10—C5	150.8 (2)
C3—C4—C42—C41^i	−141.0 (5)	C41—C4—C10—C5	40.7 (3)
C41—C4—C42—C41^i	−26.4 (5)	C41^i—C4—C10—C5	−40.7 (3)
C42^i—C4—C42—C3^i	88.3 (12)

Symmetry code: (i) x, −y+1/2, z.

(a329) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 647.07 (18) Å^3
Mr = 234.28	Z = 2
P21/m, monoclinic	F(000) = 252
a = 9.756 (1) Å	Dx = 1.202 Mg m^−3
b = 6.947 (1) Å	Cu Kα radiation, λ = 1.54178 Å
c = 9.575 (2) Å	µ = 0.68 mm^−1
α = 90°	T = 328 K
β = 94.36 (2)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 55.1°, θmin = 4.6°
955 measured reflections	h = −10→10
899 independent reflections	k = −7→0
742 reflections with I > 2σ(I)	l = 0→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 0.1455P] where P = (Fo^2 + 2Fc^2)/3
S = 1.32	(Δ/σ)max = 1.155
899 reflections	Δρmax = 0.21 e Å^−3
159 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (6)

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)
O1	0.1034 (2)	0.2500	0.4959 (3)	0.0726 (10)
O2	−0.1143 (3)	0.2500	0.5229 (4)	0.1117 (15)
O6	0.6494 (3)	0.2500	0.6762 (3)	0.0656 (9)
H6	0.711 (7)	0.2500	0.621 (6)	0.13 (2)*
C2	−0.0001 (4)	0.2500	0.5738 (5)	0.0727 (13)
C3	0.0384 (5)	0.3567 (10)	0.7110 (6)	0.0790 (19)	0.50
H3A	−0.050 (7)	0.350 (9)	0.778 (7)	0.12 (2)*	0.50
H3B	0.092 (4)	0.525 (6)	0.738 (4)	0.034 (10)*	0.50
C4	0.1626 (4)	0.2500	0.7909 (4)	0.0699 (13)
C41	0.1909 (8)	0.3884 (17)	0.9172 (7)	0.114 (3)	0.50
H41A	0.2176	0.5173	0.8868	0.03 (4)*	0.25
H41B	0.2735	0.3429	0.9782	0.08 (4)*	0.25
H41C	0.1178	0.3996	0.9752	0.027 (18)*	0.25
H41D	0.1883	0.3226	1.0067	0.15 (7)*	0.25
H41E	0.1324	0.4970	0.9153	2 (4)*	0.25
H41F	0.2881	0.4403	0.9183	0.19 (8)*	0.25
C42	0.1260 (10)	0.0488 (13)	0.8271 (11)	0.103 (2)*	0.50
H42A	0.0560	0.0561	0.8935	0.09 (4)*	0.25
H42B	0.2083	−0.0072	0.8775	0.11 (11)*	0.25
H42C	0.0991	−0.0196	0.7489	2 (5)*	0.25
H42D	0.1863	−0.0365	0.7865	2 (5)*	0.25
H42E	0.0340	0.0267	0.8024	0.4 (2)*	0.25
H42F	0.1431	0.0391	0.9310	0.08 (4)*	0.25
C5	0.4201 (3)	0.2500	0.7319 (3)	0.0485 (9)
C51	0.4805 (6)	0.2500	0.8829 (5)	0.0858 (17)
H51A	0.554 (10)	0.2500	0.890 (9)	0.20 (4)*
H51C	0.439 (4)	0.146 (6)	0.939 (4)	0.143 (16)*
C6	0.5136 (3)	0.2500	0.6287 (4)	0.0455 (9)
C7	0.4730 (3)	0.2500	0.4858 (3)	0.0430 (9)
C71	0.5796 (4)	0.2500	0.3806 (5)	0.0592 (12)
H71A	0.535 (6)	0.2500	0.291 (6)	0.12 (2)*
H71B	0.641 (3)	0.150 (5)	0.393 (3)	0.098 (11)*
C8	0.3335 (3)	0.2500	0.4449 (3)	0.0443 (9)
C81	0.2805 (5)	0.2500	0.2940 (4)	0.0601 (12)
H81A	0.189 (8)	0.2500	0.287 (6)	0.033 (17)*	0.50
H81C	0.306 (4)	0.124 (7)	0.241 (5)	0.037 (11)*	0.50
H81D	0.340 (10)	0.2500	0.250 (10)	0.07 (3)*	0.50
H81E	0.215 (6)	0.135 (8)	0.258 (5)	0.063 (14)*	0.50
C9	0.2416 (3)	0.2500	0.5493 (3)	0.0445 (9)
C10	0.2791 (3)	0.2500	0.6916 (3)	0.0478 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0348 (15)	0.119 (2)	0.0643 (16)	0.000	0.0037 (12)	0.000
O2	0.0345 (18)	0.173 (4)	0.128 (3)	0.000	0.0113 (16)	0.000
O6	0.0373 (15)	0.0766 (18)	0.0812 (19)	0.000	−0.0067 (13)	0.000
C2	0.034 (2)	0.105 (3)	0.081 (3)	0.000	0.0129 (19)	0.000
C3	0.045 (3)	0.120 (5)	0.075 (3)	0.022 (3)	0.020 (2)	−0.001 (4)
C4	0.062 (3)	0.092 (3)	0.058 (2)	0.000	0.0213 (19)	0.000
C41	0.097 (6)	0.183 (9)	0.065 (4)	0.055 (6)	0.034 (4)	−0.031 (5)
C5	0.048 (2)	0.047 (2)	0.050 (2)	0.000	−0.0006 (16)	0.000
C51	0.074 (3)	0.127 (5)	0.054 (2)	0.000	−0.008 (2)	0.000
C6	0.0327 (18)	0.0393 (19)	0.063 (2)	0.000	−0.0036 (15)	0.000
C7	0.0361 (18)	0.0372 (18)	0.056 (2)	0.000	0.0092 (15)	0.000
C71	0.044 (2)	0.061 (3)	0.075 (3)	0.000	0.021 (2)	0.000
C8	0.0423 (19)	0.044 (2)	0.0473 (19)	0.000	0.0076 (14)	0.000
C81	0.052 (3)	0.078 (4)	0.050 (2)	0.000	0.002 (2)	0.000
C9	0.0288 (17)	0.053 (2)	0.051 (2)	0.000	0.0009 (14)	0.000
C10	0.044 (2)	0.049 (2)	0.051 (2)	0.000	0.0089 (15)	0.000

Geometric parameters (Å, º)

O1—C2	1.300 (4)	C42—C41^i	1.119 (12)
O1—C9	1.405 (4)	C42—C3^i	1.501 (12)
O2—C2	1.182 (5)	C42—H42A	0.969 (9)
O6—C6	1.367 (4)	C42—H42B	0.984 (10)
O6—H6	0.83 (6)	C42—H42C	0.908 (11)
C2—C3	1.530 (7)	C42—H42D	0.939 (9)
C2—C3^i	1.530 (7)	C42—H42E	0.924 (10)
C3—C3^i	1.483 (15)	C42—H42F	0.999 (10)
C3—C42^i	1.501 (12)	C5—C6	1.394 (5)
C3—C4	1.569 (7)	C5—C10	1.400 (5)
C3—H3A	1.12 (7)	C5—C51	1.519 (5)
C3—H3B	1.30 (4)	C51—H51A	0.72 (10)
C4—C42^i	1.490 (9)	C51—H51C	1.00 (4)
C4—C42	1.490 (9)	C6—C7	1.395 (5)
C4—C10	1.537 (5)	C7—C8	1.387 (4)
C4—C3^i	1.569 (7)	C7—C71	1.503 (5)
C4—C41	1.554 (9)	C71—H71A	0.93 (6)
C4—C41^i	1.554 (9)	C71—H71B	0.92 (3)
C41—C42^i	1.119 (12)	C8—C9	1.393 (4)
C41—C41^i	1.92 (2)	C8—C81	1.498 (5)
C41—H41A	0.983 (12)	C81—H81A	0.89 (7)
C41—H41B	1.009 (8)	C81—H81C	1.05 (5)
C41—H41C	0.940 (7)	C81—H81D	0.74 (10)
C41—H41D	0.973 (9)	C81—H81E	1.06 (6)
C41—H41E	0.945 (9)	C9—C10	1.384 (5)
C41—H41F	1.014 (9)
C2—O1—C9	123.8 (3)	H41A—C41—H41F	53.9 (6)
C6—O6—H6	121 (4)	H41B—C41—H41F	53.1 (4)
O2—C2—O1	120.8 (4)	H41C—C41—H41F	135.7 (9)
O2—C2—C3	121.1 (3)	H41D—C41—H41F	104.2 (7)
O1—C2—C3	110.0 (3)	H41E—C41—H41F	106.2 (11)
O2—C2—C3^i	121.1 (3)	C41^i—C42—C4	71.5 (8)
O1—C2—C3^i	110.0 (3)	C41^i—C42—C3^i	131.1 (10)
C3—C2—C3^i	58.0 (5)	C4—C42—C3^i	63.3 (5)
C3^i—C3—C42^i	115.9 (5)	C41^i—C42—H42A	81.9 (9)
C3^i—C3—C2	61.0 (3)	C4—C42—H42A	107.2 (7)
C42^i—C3—C2	159.5 (5)	C3^i—C42—H42A	94.1 (7)
C3^i—C3—C4	61.8 (3)	C41^i—C42—H42B	52.0 (8)
C42^i—C3—C4	58.0 (4)	C4—C42—H42B	106.5 (8)
C2—C3—C4	108.6 (4)	C3^i—C42—H42B	158.9 (9)
C3^i—C3—H3A	88 (3)	H42A—C42—H42B	106.7 (9)
C42^i—C3—H3A	91 (3)	C41^i—C42—H42C	161.9 (12)
C2—C3—H3A	109 (3)	C4—C42—H42C	111.0 (8)
C4—C3—H3A	108 (3)	C3^i—C42—H42C	60.4 (6)
C3^i—C3—H3B	154.4 (18)	H42A—C42—H42C	113.2 (10)
C42^i—C3—H3B	42.5 (18)	H42B—C42—H42C	111.8 (9)
C2—C3—H3B	132 (2)	C41^i—C42—H42D	103.3 (11)
C4—C3—H3B	92.7 (19)	C4—C42—H42D	109.1 (7)
H3A—C3—H3B	104 (4)	C3^i—C42—H42D	108.0 (9)
C42^i—C4—C42	139.5 (7)	H42A—C42—H42D	143.0 (10)
C42^i—C4—C10	110.2 (4)	H42B—C42—H42D	56.1 (5)
C42—C4—C10	110.2 (4)	H42C—C42—H42D	58.6 (6)
C42^i—C4—C3^i	111.6 (5)	C41^i—C42—H42E	138.0 (11)
C42—C4—C3^i	58.7 (5)	C4—C42—H42E	109.9 (8)
C10—C4—C3^i	106.2 (3)	C3^i—C42—H42E	52.8 (5)
C42^i—C4—C3	58.7 (5)	H42A—C42—H42E	57.1 (5)
C42—C4—C3	111.6 (5)	H42B—C42—H42E	143.1 (10)
C10—C4—C3	106.2 (3)	H42C—C42—H42E	59.2 (7)
C3^i—C4—C3	56.4 (6)	H42D—C42—H42E	114.6 (11)
C42^i—C4—C41	43.1 (5)	C41^i—C42—H42F	38.4 (5)
C42—C4—C41	115.5 (6)	C4—C42—H42F	105.7 (8)
C10—C4—C41	112.7 (4)	C3^i—C42—H42F	144.1 (9)
C3^i—C4—C41	139.2 (4)	H42A—C42—H42F	54.7 (5)
C3—C4—C41	99.9 (4)	H42B—C42—H42F	54.3 (6)
C42^i—C4—C41^i	115.5 (6)	H42C—C42—H42F	143.3 (10)
C42—C4—C41^i	43.1 (5)	H42D—C42—H42F	108.0 (9)
C10—C4—C41^i	112.7 (4)	H42E—C42—H42F	109.2 (9)
C3^i—C4—C41^i	99.9 (4)	C6—C5—C10	119.1 (3)
C3—C4—C41^i	139.2 (4)	C6—C5—C51	116.6 (4)
C41—C4—C41^i	76.5 (8)	C10—C5—C51	124.3 (4)
C42^i—C41—C4	65.4 (6)	C5—C51—H51A	114 (7)
C42^i—C41—C41^i	113.0 (7)	C5—C51—H51C	112 (2)
C4—C41—C41^i	51.8 (4)	H51A—C51—H51C	113 (5)
C42^i—C41—H41A	64.1 (8)	O6—C6—C5	115.7 (3)
C4—C41—H41A	111.6 (6)	O6—C6—C7	121.5 (3)
C41^i—C41—H41A	155.7 (4)	C5—C6—C7	122.9 (3)
C42^i—C41—H41B	161.4 (10)	C8—C7—C6	118.4 (3)
C4—C41—H41B	110.1 (7)	C8—C7—C71	121.7 (3)
C41^i—C41—H41B	71.8 (6)	C6—C7—C71	119.9 (3)
H41A—C41—H41B	103.8 (9)	C7—C71—H71A	109 (3)
C42^i—C41—H41C	90.8 (8)	C7—C71—H71B	113.0 (19)
C4—C41—H41C	114.4 (8)	H71A—C71—H71B	112 (3)
C41^i—C41—H41C	94.8 (7)	C7—C8—C9	118.0 (3)
H41A—C41—H41C	109.2 (9)	C7—C8—C81	122.2 (3)
H41B—C41—H41C	107.0 (7)	C9—C8—C81	119.9 (3)
C42^i—C41—H41D	144.2 (10)	C8—C81—H81A	110 (4)
C4—C41—H41D	112.3 (9)	C8—C81—H81C	113 (2)
C41^i—C41—H41D	62.0 (6)	H81A—C81—H81C	104 (3)
H41A—C41—H41D	135.6 (9)	C8—C81—H81D	108 (7)
H41B—C41—H41D	54.3 (5)	H81A—C81—H81D	142 (8)
H41C—C41—H41D	56.5 (5)	H81C—C81—H81D	60 (3)
C42^i—C41—H41E	50.8 (7)	C8—C81—H81E	118 (3)
C4—C41—H41E	114.0 (7)	H81A—C81—H81E	53 (3)
C41^i—C41—H41E	143.0 (6)	H81C—C81—H81E	52 (3)
H41A—C41—H41E	56.0 (6)	H81D—C81—H81E	107 (6)
H41B—C41—H41E	135.7 (9)	C10—C9—C8	124.7 (3)
H41C—C41—H41E	57.4 (4)	C10—C9—O1	122.2 (3)
H41D—C41—H41E	109.7 (6)	C8—C9—O1	113.0 (3)
C42^i—C41—H41F	110.0 (11)	C9—C10—C5	116.9 (3)
C4—C41—H41F	109.8 (5)	C9—C10—C4	117.2 (3)
C41^i—C41—H41F	110.8 (6)	C5—C10—C4	126.0 (3)
C9—O1—C2—O2	180.0	C10—C4—C42—C3^i	−97.1 (4)
C9—O1—C2—C3	31.0 (3)	C3—C4—C42—C3^i	20.6 (5)
C9—O1—C2—C3^i	−31.0 (3)	C41—C4—C42—C3^i	133.8 (5)
O2—C2—C3—C3^i	109.5 (3)	C41^i—C4—C42—C3^i	160.9 (8)
O1—C2—C3—C3^i	−101.6 (2)	C10—C5—C6—O6	180.0
O2—C2—C3—C42^i	−163.6 (17)	C51—C5—C6—O6	0.0
O1—C2—C3—C42^i	−14.7 (19)	C10—C5—C6—C7	0.0
C3^i—C2—C3—C42^i	87.0 (19)	C51—C5—C6—C7	180.0
O2—C2—C3—C4	150.3 (3)	O6—C6—C7—C8	180.0
O1—C2—C3—C4	−60.8 (4)	C5—C6—C7—C8	0.0
C3^i—C2—C3—C4	40.8 (4)	O6—C6—C7—C71	0.0
C3^i—C3—C4—C42^i	−156.9 (4)	C5—C6—C7—C71	180.0
C2—C3—C4—C42^i	162.7 (6)	C6—C7—C8—C9	0.0
C3^i—C3—C4—C42	−21.1 (4)	C71—C7—C8—C9	180.0
C42^i—C3—C4—C42	135.8 (8)	C6—C7—C8—C81	180.0
C2—C3—C4—C42	−61.6 (6)	C71—C7—C8—C81	0.0
C3^i—C3—C4—C10	98.9 (2)	C7—C8—C9—C10	0.0
C42^i—C3—C4—C10	−104.2 (4)	C81—C8—C9—C10	180.0
C2—C3—C4—C10	58.5 (4)	C7—C8—C9—O1	180.0
C42^i—C3—C4—C3^i	156.9 (4)	C81—C8—C9—O1	0.0
C2—C3—C4—C3^i	−40.4 (4)	C2—O1—C9—C10	0.0
C3^i—C3—C4—C41	−143.8 (4)	C2—O1—C9—C8	180.0
C42^i—C3—C4—C41	13.1 (6)	C8—C9—C10—C5	0.0
C2—C3—C4—C41	175.8 (5)	O1—C9—C10—C5	180.0
C3^i—C3—C4—C41^i	−63.0 (7)	C8—C9—C10—C4	180.0
C42^i—C3—C4—C41^i	93.9 (9)	O1—C9—C10—C4	0.0
C2—C3—C4—C41^i	−103.5 (8)	C6—C5—C10—C9	0.0
C42—C4—C41—C42^i	−136.3 (10)	C51—C5—C10—C9	180.0
C10—C4—C41—C42^i	95.8 (6)	C6—C5—C10—C4	180.0
C3^i—C4—C41—C42^i	−65.4 (10)	C51—C5—C10—C4	0.000 (1)
C3—C4—C41—C42^i	−16.5 (7)	C42^i—C4—C10—C9	−91.5 (5)
C41^i—C4—C41—C42^i	−155.0 (6)	C42—C4—C10—C9	91.5 (5)
C42^i—C4—C41—C41^i	155.0 (6)	C3^i—C4—C10—C9	29.5 (3)
C42—C4—C41—C41^i	18.7 (5)	C3—C4—C10—C9	−29.5 (3)
C10—C4—C41—C41^i	−109.2 (4)	C41—C4—C10—C9	−137.9 (4)
C3^i—C4—C41—C41^i	89.5 (7)	C41^i—C4—C10—C9	137.9 (4)
C3—C4—C41—C41^i	138.5 (4)	C42^i—C4—C10—C5	88.5 (5)
C42^i—C4—C42—C41^i	−73.7 (15)	C42—C4—C10—C5	−88.5 (5)
C10—C4—C42—C41^i	102.0 (7)	C3^i—C4—C10—C5	−150.5 (3)
C3^i—C4—C42—C41^i	−160.9 (8)	C3—C4—C10—C5	150.5 (3)
C3—C4—C42—C41^i	−140.3 (6)	C41—C4—C10—C5	42.1 (4)
C41—C4—C42—C41^i	−27.1 (7)	C41^i—C4—C10—C5	−42.1 (4)
C42^i—C4—C42—C3^i	87.2 (13)

Symmetry code: (i) x, −y+1/2, z.

(cum110c) 6-hydroxy-4,4,5,7,8-pentamethylo-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1248.7 (6) Å^3
Mr = 234.28	Z = 4
P21/n, monoclinic	F(000) = 504
a = 13.449 (4) Å	Dx = 1.246 Mg m^−3
b = 6.757 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.746 (4) Å	µ = 0.09 mm^−1
α = 90°	T = 110 K
β = 91.54 (2)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 29.6°, θmin = 2.1°
8052 measured reflections	h = −18→17
3237 independent reflections	k = −9→5
1764 reflections with I > 2σ(I)	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.205	w = 1/[σ^2(Fo^2) + (0.0909P)^2 + 0.920P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.438
3237 reflections	Δρmax = 0.34 e Å^−3
227 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (17)

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	0.79680 (13)	0.2079 (3)	−0.30433 (13)	0.0209 (4)
O6	1.15842 (13)	0.2488 (3)	−0.48101 (14)	0.0218 (4)
H6	1.161 (3)	0.259 (5)	−0.548 (3)	0.050 (11)*
O2	0.70025 (14)	0.2076 (3)	−0.17918 (14)	0.0305 (5)
C2	0.78184 (19)	0.2434 (4)	−0.20983 (19)	0.0220 (6)
C3	0.8679 (2)	0.3273 (5)	−0.1533 (2)	0.0246 (6)
H3A	0.853 (2)	0.313 (5)	−0.084 (3)	0.039 (9)*
H3B	0.873 (2)	0.471 (5)	−0.174 (2)	0.035 (9)*
C4	0.96643 (19)	0.2220 (4)	−0.17629 (18)	0.0205 (6)
C41	1.0462 (2)	0.3314 (5)	−0.1150 (2)	0.0297 (7)
H41A	1.019 (3)	0.347 (5)	−0.048 (3)	0.048 (10)*
H41B	1.056 (2)	0.467 (6)	−0.142 (3)	0.045 (10)*
H41C	1.109 (3)	0.260 (5)	−0.109 (3)	0.042 (10)*
C42	0.9609 (3)	0.0038 (5)	−0.1448 (2)	0.0294 (7)
H42A	0.943 (2)	−0.007 (5)	−0.075 (3)	0.034 (9)*
H42B	1.026 (2)	−0.059 (5)	−0.154 (2)	0.034 (9)*
H42C	0.905 (3)	−0.072 (5)	−0.182 (3)	0.041 (9)*
C5	1.06907 (18)	0.2305 (4)	−0.33569 (18)	0.0176 (5)
C51	1.1700 (2)	0.2060 (5)	−0.2854 (2)	0.0259 (6)
H51A	1.220 (2)	0.154 (5)	−0.330 (2)	0.031 (9)*
H51B	1.165 (2)	0.102 (4)	−0.228 (2)	0.024 (8)*
H51C	1.194 (3)	0.339 (5)	−0.257 (3)	0.051 (10)*
C6	1.06783 (17)	0.2440 (4)	−0.43768 (19)	0.0176 (5)
C7	0.97903 (18)	0.2523 (4)	−0.49408 (18)	0.0169 (5)
C71	0.9845 (2)	0.2615 (4)	−0.60336 (19)	0.0209 (6)
H71A	1.024 (2)	0.145 (5)	−0.629 (2)	0.030 (9)*
H71B	1.022 (3)	0.379 (5)	−0.629 (2)	0.045 (10)*
H71C	0.919 (3)	0.256 (5)	−0.634 (2)	0.033 (9)*
C8	0.88875 (18)	0.2462 (4)	−0.44611 (18)	0.0175 (5)
C81	0.7903 (2)	0.2519 (4)	−0.5014 (2)	0.0228 (6)
H81A	0.783 (3)	0.363 (6)	−0.544 (3)	0.058 (11)*
H81B	0.733 (3)	0.269 (5)	−0.455 (3)	0.038 (9)*
H81C	0.775 (3)	0.134 (5)	−0.537 (3)	0.049 (10)*
C9	0.89105 (18)	0.2349 (4)	−0.34514 (18)	0.0169 (5)
C10	0.97875 (18)	0.2318 (4)	−0.28730 (18)	0.0177 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0153 (9)	0.0307 (11)	0.0168 (9)	−0.0024 (7)	0.0015 (7)	−0.0011 (8)
O6	0.0148 (9)	0.0287 (10)	0.0223 (10)	−0.0003 (7)	0.0065 (7)	0.0003 (8)
O2	0.0225 (10)	0.0438 (13)	0.0255 (10)	−0.0021 (9)	0.0076 (8)	−0.0006 (9)
C2	0.0218 (13)	0.0246 (14)	0.0199 (12)	0.0027 (11)	0.0063 (10)	0.0016 (10)
C3	0.0232 (14)	0.0322 (16)	0.0186 (13)	0.0011 (12)	0.0029 (11)	−0.0023 (12)
C4	0.0186 (12)	0.0271 (14)	0.0160 (12)	0.0007 (10)	0.0010 (9)	−0.0010 (10)
C41	0.0260 (16)	0.0407 (18)	0.0223 (15)	−0.0019 (13)	−0.0039 (12)	−0.0064 (13)
C42	0.0296 (17)	0.0344 (17)	0.0243 (15)	0.0004 (13)	0.0016 (13)	0.0045 (12)
C5	0.0143 (11)	0.0188 (12)	0.0196 (12)	−0.0004 (9)	−0.0006 (9)	0.0002 (10)
C51	0.0184 (13)	0.0351 (17)	0.0241 (14)	0.0019 (12)	0.0006 (11)	−0.0011 (12)
C6	0.0145 (11)	0.0155 (12)	0.0231 (13)	−0.0002 (9)	0.0035 (10)	−0.0018 (10)
C7	0.0197 (12)	0.0147 (11)	0.0165 (12)	−0.0006 (10)	0.0007 (9)	−0.0008 (9)
C71	0.0209 (13)	0.0229 (14)	0.0190 (12)	0.0000 (11)	0.0029 (10)	−0.0009 (11)
C8	0.0188 (12)	0.0159 (12)	0.0178 (12)	−0.0003 (10)	−0.0001 (9)	−0.0006 (10)
C81	0.0213 (13)	0.0278 (15)	0.0191 (13)	0.0015 (11)	−0.0010 (10)	−0.0005 (12)
C9	0.0144 (11)	0.0178 (12)	0.0186 (12)	−0.0020 (9)	0.0028 (9)	−0.0003 (10)
C10	0.0167 (12)	0.0190 (13)	0.0173 (12)	0.0009 (10)	−0.0007 (9)	−0.0002 (10)

Geometric parameters (Å, º)

O1—C2	1.341 (3)	C5—C10	1.401 (4)
O1—C9	1.412 (3)	C5—C6	1.405 (3)
O6—C6	1.371 (3)	C5—C51	1.515 (4)
O2—C2	1.210 (3)	C6—C7	1.407 (3)
C2—C3	1.489 (4)	C7—C8	1.398 (4)
C3—C4	1.544 (4)	C7—C71	1.507 (3)
C4—C41	1.536 (4)	C8—C9	1.390 (3)
C4—C42	1.539 (4)	C8—C81	1.508 (4)
C4—C10	1.541 (4)	C9—C10	1.405 (3)
C2—O1—C9	121.43 (19)	O6—C6—C7	120.7 (2)
O2—C2—O1	117.5 (2)	C5—C6—C7	122.7 (2)
O2—C2—C3	126.4 (2)	C8—C7—C6	118.3 (2)
O1—C2—C3	116.0 (2)	C8—C7—C71	122.5 (2)
C2—C3—C4	112.1 (2)	C6—C7—C71	119.2 (2)
C41—C4—C42	110.2 (2)	C9—C8—C7	118.5 (2)
C41—C4—C10	115.5 (2)	C9—C8—C81	120.0 (2)
C42—C4—C10	109.1 (2)	C7—C8—C81	121.6 (2)
C41—C4—C3	104.9 (2)	C8—C9—C10	124.2 (2)
C42—C4—C3	109.6 (2)	C8—C9—O1	114.1 (2)
C10—C4—C3	107.4 (2)	C10—C9—O1	121.5 (2)
C10—C5—C6	119.1 (2)	C5—C10—C9	117.2 (2)
C10—C5—C51	124.2 (2)	C5—C10—C4	126.0 (2)
C6—C5—C51	116.6 (2)	C9—C10—C4	116.8 (2)
O6—C6—C5	116.6 (2)
C9—O1—C2—O2	−176.4 (2)	C81—C8—C9—C10	−179.0 (2)
C9—O1—C2—C3	4.7 (3)	C7—C8—C9—O1	−173.5 (2)
O2—C2—C3—C4	137.2 (3)	C81—C8—C9—O1	6.6 (3)
O1—C2—C3—C4	−44.1 (3)	C2—O1—C9—C8	−163.0 (2)
C2—C3—C4—C41	178.1 (2)	C2—O1—C9—C10	22.4 (3)
C2—C3—C4—C42	−63.7 (3)	C6—C5—C10—C9	3.7 (4)
C2—C3—C4—C10	54.7 (3)	C51—C5—C10—C9	−173.4 (2)
C10—C5—C6—O6	177.8 (2)	C6—C5—C10—C4	−178.9 (2)
C51—C5—C6—O6	−4.8 (3)	C51—C5—C10—C4	4.0 (4)
C10—C5—C6—C7	−2.1 (4)	C8—C9—C10—C5	−3.2 (4)
C51—C5—C6—C7	175.2 (2)	O1—C9—C10—C5	170.8 (2)
O6—C6—C7—C8	179.8 (2)	C8—C9—C10—C4	179.1 (2)
C5—C6—C7—C8	−0.2 (4)	O1—C9—C10—C4	−6.9 (3)
O6—C6—C7—C71	1.5 (4)	C41—C4—C10—C5	35.9 (4)
C5—C6—C7—C71	−178.5 (2)	C42—C4—C10—C5	−88.8 (3)
C6—C7—C8—C9	0.8 (3)	C3—C4—C10—C5	152.5 (3)
C71—C7—C8—C9	179.0 (2)	C41—C4—C10—C9	−146.7 (3)
C6—C7—C8—C81	−179.3 (2)	C42—C4—C10—C9	88.6 (3)
C71—C7—C8—C81	−1.1 (4)	C3—C4—C10—C9	−30.1 (3)
C7—C8—C9—C10	0.9 (4)

(cum150c) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1256.0 (6) Å^3
Mr = 234.28	Z = 4
P21/n, monoclinic	F(000) = 504
a = 13.429 (4) Å	Dx = 1.239 Mg m^−3
b = 6.784 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.792 (4) Å	µ = 0.09 mm^−1
α = 90°	T = 150 K
β = 91.54 (2)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 30.2°, θmin = 3.0°
10354 measured reflections	h = −18→18
3323 independent reflections	k = −9→5
2085 reflections with I > 2σ(I)	l = −18→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 0.350P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.010
3323 reflections	Δρmax = 0.34 e Å^−3
227 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0007 (13)

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	0.79717 (9)	0.20793 (19)	−0.30444 (8)	0.0239 (3)
O6	1.15870 (9)	0.24886 (19)	−0.48134 (10)	0.0260 (3)
H6	1.1537 (19)	0.262 (3)	−0.542 (2)	0.049 (8)*
O2	0.70072 (10)	0.2078 (2)	−0.17939 (10)	0.0363 (4)
C2	0.78223 (14)	0.2439 (3)	−0.20981 (13)	0.0257 (4)
C3	0.86865 (14)	0.3271 (3)	−0.15457 (13)	0.0286 (4)
H3A	0.8527 (16)	0.317 (3)	−0.0854 (16)	0.034 (6)*
H3B	0.8710 (15)	0.470 (3)	−0.1747 (14)	0.033 (6)*
C4	0.96725 (13)	0.2227 (3)	−0.17730 (12)	0.0243 (4)
C41	1.04704 (17)	0.3337 (4)	−0.11738 (16)	0.0379 (5)
H41A	1.0226 (18)	0.351 (3)	−0.0525 (18)	0.047 (6)*
H41B	1.0586 (18)	0.463 (4)	−0.1457 (17)	0.048 (7)*
H41C	1.115 (2)	0.262 (3)	−0.1131 (18)	0.049 (7)*
C42	0.96290 (19)	0.0062 (3)	−0.14531 (16)	0.0350 (5)
H42A	0.9492 (17)	−0.002 (3)	−0.0779 (17)	0.045 (6)*
H42B	1.0287 (17)	−0.066 (3)	−0.1580 (15)	0.040 (6)*
H42C	0.9098 (17)	−0.067 (3)	−0.1820 (16)	0.036 (6)*
C5	1.06963 (12)	0.2313 (2)	−0.33677 (12)	0.0201 (4)
C51	1.17061 (14)	0.2077 (4)	−0.28716 (15)	0.0303 (5)
H51A	1.2193 (18)	0.149 (3)	−0.3327 (17)	0.046 (6)*
H51B	1.1706 (16)	0.106 (3)	−0.2344 (16)	0.035 (6)*
H51C	1.197 (2)	0.336 (4)	−0.2593 (18)	0.058 (7)*
C6	1.06766 (12)	0.2447 (2)	−0.43843 (12)	0.0192 (4)
C7	0.97892 (12)	0.2527 (2)	−0.49386 (12)	0.0186 (4)
C71	0.98361 (15)	0.2614 (3)	−0.60288 (13)	0.0241 (4)
H71A	1.0195 (16)	0.147 (3)	−0.6283 (15)	0.039 (6)*
H71B	1.0187 (18)	0.379 (4)	−0.6260 (16)	0.051 (7)*
H71C	0.918 (2)	0.263 (3)	−0.6337 (18)	0.051 (7)*
C8	0.88857 (12)	0.2457 (2)	−0.44630 (12)	0.0186 (4)
C81	0.78991 (14)	0.2511 (3)	−0.50047 (14)	0.0253 (4)
H81A	0.786 (2)	0.355 (4)	−0.549 (2)	0.063 (8)*
H81B	0.734 (2)	0.262 (4)	−0.459 (2)	0.066 (8)*
H81C	0.778 (2)	0.134 (4)	−0.5394 (19)	0.064 (8)*
C9	0.89165 (12)	0.2346 (2)	−0.34520 (12)	0.0182 (4)
C10	0.97912 (12)	0.2320 (2)	−0.28794 (12)	0.0189 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0178 (6)	0.0354 (8)	0.0188 (6)	−0.0021 (5)	0.0046 (5)	−0.0003 (5)
O6	0.0176 (6)	0.0339 (8)	0.0268 (7)	0.0005 (5)	0.0063 (5)	0.0010 (6)
O2	0.0254 (7)	0.0549 (10)	0.0293 (7)	−0.0031 (7)	0.0124 (6)	−0.0024 (7)
C2	0.0256 (9)	0.0303 (10)	0.0215 (8)	0.0043 (8)	0.0072 (7)	0.0019 (7)
C3	0.0282 (10)	0.0380 (12)	0.0199 (9)	0.0031 (9)	0.0042 (7)	−0.0052 (8)
C4	0.0220 (8)	0.0339 (10)	0.0168 (8)	0.0009 (8)	−0.0001 (6)	−0.0007 (7)
C41	0.0316 (11)	0.0561 (16)	0.0258 (10)	−0.0008 (11)	−0.0044 (8)	−0.0128 (10)
C42	0.0401 (13)	0.0409 (13)	0.0241 (10)	0.0041 (10)	0.0020 (9)	0.0080 (9)
C5	0.0183 (8)	0.0187 (9)	0.0232 (8)	−0.0001 (7)	0.0002 (6)	0.0003 (6)
C51	0.0197 (9)	0.0419 (13)	0.0293 (10)	0.0043 (8)	−0.0024 (8)	−0.0010 (9)
C6	0.0154 (7)	0.0187 (9)	0.0239 (8)	−0.0007 (6)	0.0059 (6)	−0.0008 (7)
C7	0.0217 (8)	0.0165 (8)	0.0177 (8)	−0.0001 (7)	0.0032 (6)	0.0001 (6)
C71	0.0273 (9)	0.0261 (10)	0.0191 (8)	−0.0008 (8)	0.0064 (7)	−0.0007 (7)
C8	0.0186 (8)	0.0179 (9)	0.0194 (8)	0.0002 (6)	0.0010 (6)	−0.0006 (6)
C81	0.0200 (8)	0.0352 (11)	0.0206 (8)	−0.0003 (8)	−0.0013 (7)	−0.0005 (8)
C9	0.0165 (7)	0.0182 (8)	0.0201 (8)	−0.0012 (6)	0.0054 (6)	−0.0008 (6)
C10	0.0190 (8)	0.0203 (9)	0.0174 (7)	0.0002 (7)	0.0006 (6)	−0.0003 (6)

Geometric parameters (Å, º)

O1—C2	1.348 (2)	C5—C6	1.405 (2)
O1—C9	1.4131 (19)	C5—C10	1.405 (2)
O6—C6	1.3727 (19)	C5—C51	1.511 (2)
O2—C2	1.208 (2)	C6—C7	1.400 (2)
C2—C3	1.483 (3)	C7—C8	1.396 (2)
C3—C4	1.541 (3)	C7—C71	1.508 (2)
C4—C41	1.533 (3)	C8—C9	1.396 (2)
C4—C42	1.535 (3)	C8—C81	1.504 (2)
C4—C10	1.540 (2)	C9—C10	1.398 (2)
C2—O1—C9	121.37 (13)	O6—C6—C5	116.02 (15)
O2—C2—O1	117.36 (17)	C7—C6—C5	122.73 (14)
O2—C2—C3	127.07 (16)	C8—C7—C6	118.70 (15)
O1—C2—C3	115.56 (15)	C8—C7—C71	122.02 (16)
C2—C3—C4	112.67 (16)	C6—C7—C71	119.24 (15)
C41—C4—C42	110.27 (18)	C7—C8—C9	117.94 (15)
C41—C4—C10	115.13 (16)	C7—C8—C81	122.08 (15)
C42—C4—C10	109.25 (15)	C9—C8—C81	119.98 (15)
C41—C4—C3	104.86 (16)	C8—C9—C10	124.53 (14)
C42—C4—C3	109.97 (16)	C8—C9—O1	113.67 (14)
C10—C4—C3	107.17 (14)	C10—C9—O1	121.57 (14)
C6—C5—C10	119.01 (15)	C9—C10—C5	116.99 (15)
C6—C5—C51	116.84 (15)	C9—C10—C4	116.91 (14)
C10—C5—C51	124.10 (16)	C5—C10—C4	126.06 (15)
O6—C6—C7	121.25 (15)
C9—O1—C2—O2	−176.27 (16)	C81—C8—C9—C10	−178.95 (17)
C9—O1—C2—C3	4.6 (2)	C7—C8—C9—O1	−173.86 (15)
O2—C2—C3—C4	136.8 (2)	C81—C8—C9—O1	6.5 (2)
O1—C2—C3—C4	−44.1 (2)	C2—O1—C9—C8	−162.86 (16)
C2—C3—C4—C41	177.71 (17)	C2—O1—C9—C10	22.4 (2)
C2—C3—C4—C42	−63.7 (2)	C8—C9—C10—C5	−3.1 (3)
C2—C3—C4—C10	54.9 (2)	O1—C9—C10—C5	171.06 (15)
C10—C5—C6—O6	178.22 (16)	C8—C9—C10—C4	179.02 (15)
C51—C5—C6—O6	−4.5 (2)	O1—C9—C10—C4	−6.9 (2)
C10—C5—C6—C7	−2.0 (3)	C6—C5—C10—C9	3.6 (2)
C51—C5—C6—C7	175.32 (17)	C51—C5—C10—C9	−173.51 (17)
O6—C6—C7—C8	179.31 (16)	C6—C5—C10—C4	−178.71 (16)
C5—C6—C7—C8	−0.5 (2)	C51—C5—C10—C4	4.2 (3)
O6—C6—C7—C71	1.4 (2)	C41—C4—C10—C9	−146.16 (18)
C5—C6—C7—C71	−178.39 (16)	C42—C4—C10—C9	89.2 (2)
C6—C7—C8—C9	1.1 (2)	C3—C4—C10—C9	−30.0 (2)
C71—C7—C8—C9	178.99 (16)	C41—C4—C10—C5	36.1 (3)
C6—C7—C8—C81	−179.25 (17)	C42—C4—C10—C5	−88.6 (2)
C71—C7—C8—C81	−1.4 (3)	C3—C4—C10—C5	152.33 (18)
C7—C8—C9—C10	0.7 (3)

(cum220) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1277.6 (4) Å^3
Mr = 234.28	Z = 4
P21/n, monoclinic	F(000) = 504
a = 13.345 (2) Å	Dx = 1.218 Mg m^−3
b = 6.853 (1) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.973 (3) Å	µ = 0.08 mm^−1
α = 90°	T = 220 K
β = 91.25 (2)°	, colourlees
γ = 90°	0.44 × 0.38 × 0.19 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 29.4°, θmin = 3.3°
5221 measured reflections	h = −12→17
2975 independent reflections	k = −9→9
1955 reflections with I > 2σ(I)	l = −18→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.078P)^2 + 0.099P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.340
2975 reflections	Δρmax = 0.38 e Å^−3
227 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0000 (19)

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	0.79818 (7)	0.21076 (17)	−0.30423 (8)	0.0369 (3)
O6	1.15996 (8)	0.24937 (16)	−0.48359 (11)	0.0404 (3)
H6	1.1576 (18)	0.261 (3)	−0.544 (2)	0.064 (7)*
O2	0.70200 (9)	0.2102 (2)	−0.18045 (10)	0.0594 (4)
C2	0.78373 (12)	0.2462 (2)	−0.21098 (13)	0.0409 (4)
C3	0.87049 (13)	0.3313 (3)	−0.15758 (14)	0.0476 (5)
H3A	0.8550 (16)	0.319 (3)	−0.0897 (19)	0.069 (6)*
H3B	0.8739 (13)	0.470 (3)	−0.1760 (14)	0.054 (5)*
C4	0.97048 (12)	0.2307 (2)	−0.18089 (13)	0.0395 (4)
C41	1.04961 (17)	0.3449 (5)	−0.12368 (18)	0.0684 (7)
H41A	1.0207 (19)	0.367 (4)	−0.062 (2)	0.091 (8)*
H41B	1.0631 (13)	0.476 (3)	−0.1514 (14)	0.049 (6)*
H41C	1.112 (2)	0.275 (4)	−0.121 (2)	0.086 (8)*
C42	0.96690 (19)	0.0159 (4)	−0.14754 (16)	0.0619 (6)
H42A	0.9535 (16)	0.004 (4)	−0.0789 (17)	0.076 (7)*
H42B	1.0344 (19)	−0.042 (4)	−0.1539 (17)	0.082 (7)*
H42C	0.9081 (18)	−0.065 (3)	−0.1886 (17)	0.077 (7)*
C5	1.07157 (10)	0.23537 (19)	−0.33974 (12)	0.0301 (3)
C51	1.17397 (12)	0.2134 (3)	−0.29145 (16)	0.0484 (5)
H51A	1.2189 (18)	0.159 (3)	−0.3373 (17)	0.072 (6)*
H51B	1.1718 (16)	0.117 (3)	−0.2386 (17)	0.069 (7)*
H51C	1.1992 (17)	0.332 (4)	−0.2655 (17)	0.068 (6)*
C6	1.06879 (10)	0.24643 (18)	−0.43978 (12)	0.0296 (3)
C7	0.97893 (10)	0.25250 (17)	−0.49408 (11)	0.0278 (3)
C71	0.98267 (14)	0.2598 (2)	−0.60150 (12)	0.0363 (4)
H71A	1.0206 (14)	0.153 (3)	−0.6234 (14)	0.058 (6)*
H71B	1.0177 (14)	0.377 (3)	−0.6193 (14)	0.060 (6)*
H71C	0.918 (2)	0.259 (3)	−0.6340 (19)	0.074 (8)*
C8	0.88888 (10)	0.24588 (18)	−0.44551 (11)	0.0278 (3)
C81	0.78870 (12)	0.2494 (3)	−0.49783 (14)	0.0389 (4)
H81A	0.7822 (17)	0.352 (4)	−0.5422 (18)	0.074 (7)*
H81B	0.738 (2)	0.267 (4)	−0.449 (2)	0.104 (10)*
H81C	0.7775 (17)	0.138 (4)	−0.5313 (18)	0.075 (7)*
C9	0.89247 (10)	0.23684 (19)	−0.34580 (11)	0.0280 (3)
C10	0.98119 (10)	0.23652 (19)	−0.29019 (11)	0.0295 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0274 (5)	0.0535 (7)	0.0302 (7)	−0.0024 (4)	0.0078 (4)	−0.0012 (5)
O6	0.0288 (5)	0.0498 (7)	0.0433 (8)	0.0006 (4)	0.0123 (5)	0.0008 (5)
O2	0.0458 (7)	0.0868 (10)	0.0465 (9)	−0.0074 (6)	0.0218 (6)	−0.0039 (7)
C2	0.0390 (8)	0.0510 (10)	0.0333 (10)	0.0041 (6)	0.0133 (7)	0.0001 (6)
C3	0.0468 (9)	0.0613 (12)	0.0350 (11)	0.0063 (8)	0.0072 (7)	−0.0103 (8)
C4	0.0383 (8)	0.0541 (10)	0.0261 (9)	0.0055 (6)	0.0005 (6)	−0.0049 (6)
C41	0.0525 (11)	0.105 (2)	0.0474 (14)	0.0030 (12)	−0.0076 (10)	−0.0313 (13)
C42	0.0741 (14)	0.0722 (14)	0.0395 (12)	0.0161 (11)	0.0059 (10)	0.0180 (10)
C5	0.0266 (6)	0.0307 (7)	0.0329 (9)	0.0019 (5)	−0.0009 (6)	−0.0033 (5)
C51	0.0309 (8)	0.0628 (12)	0.0514 (13)	0.0059 (7)	−0.0051 (8)	−0.0065 (9)
C6	0.0268 (6)	0.0269 (7)	0.0353 (9)	−0.0003 (5)	0.0082 (6)	−0.0015 (5)
C7	0.0328 (7)	0.0247 (6)	0.0260 (8)	0.0002 (5)	0.0047 (6)	−0.0003 (5)
C71	0.0449 (9)	0.0371 (9)	0.0271 (9)	0.0001 (6)	0.0084 (7)	−0.0012 (6)
C8	0.0280 (6)	0.0286 (7)	0.0269 (8)	−0.0014 (5)	0.0007 (6)	−0.0010 (5)
C81	0.0306 (7)	0.0507 (10)	0.0353 (10)	0.0009 (6)	−0.0016 (7)	0.0004 (7)
C9	0.0254 (6)	0.0305 (7)	0.0283 (8)	−0.0001 (5)	0.0062 (5)	−0.0005 (5)
C10	0.0315 (7)	0.0312 (7)	0.0258 (8)	0.0013 (5)	−0.0002 (6)	−0.0020 (5)

Geometric parameters (Å, º)

O1—C2	1.343 (2)	C5—C6	1.400 (2)
O1—C9	1.4088 (16)	C5—C10	1.404 (2)
O6—C6	1.3740 (17)	C5—C51	1.518 (2)
O2—C2	1.205 (2)	C6—C7	1.406 (2)
C2—C3	1.483 (3)	C7—C8	1.3936 (19)
C3—C4	1.543 (2)	C7—C71	1.504 (2)
C4—C41	1.527 (3)	C8—C9	1.394 (2)
C4—C10	1.538 (2)	C8—C81	1.510 (2)
C4—C42	1.544 (3)	C9—C10	1.402 (2)
C2—O1—C9	121.69 (13)	O6—C6—C7	120.83 (15)
O2—C2—O1	117.16 (17)	C5—C6—C7	122.99 (13)
O2—C2—C3	127.22 (17)	C8—C7—C6	118.08 (14)
O1—C2—C3	115.60 (14)	C8—C7—C71	122.34 (14)
C2—C3—C4	112.77 (14)	C6—C7—C71	119.56 (13)
C41—C4—C10	115.37 (16)	C7—C8—C9	118.48 (13)
C41—C4—C3	104.58 (15)	C7—C8—C81	121.84 (15)
C10—C4—C3	107.30 (14)	C9—C8—C81	119.68 (13)
C41—C4—C42	110.87 (19)	C8—C9—C10	124.34 (13)
C10—C4—C42	109.19 (14)	C8—C9—O1	113.96 (12)
C3—C4—C42	109.25 (16)	C10—C9—O1	121.49 (14)
C6—C5—C10	119.21 (13)	C9—C10—C5	116.80 (15)
C6—C5—C51	116.95 (14)	C9—C10—C4	117.06 (13)
C10—C5—C51	123.78 (16)	C5—C10—C4	126.10 (14)
O6—C6—C5	116.18 (14)
C9—O1—C2—O2	−176.22 (14)	C81—C8—C9—C10	−178.76 (13)
C9—O1—C2—C3	5.4 (2)	C7—C8—C9—O1	−173.90 (11)
O2—C2—C3—C4	137.63 (19)	C81—C8—C9—O1	6.46 (18)
O1—C2—C3—C4	−44.2 (2)	C2—O1—C9—C8	−163.41 (13)
C2—C3—C4—C41	177.12 (19)	C2—O1—C9—C10	21.6 (2)
C2—C3—C4—C10	54.1 (2)	C8—C9—C10—C5	−3.3 (2)
C2—C3—C4—C42	−64.2 (2)	O1—C9—C10—C5	171.07 (12)
C10—C5—C6—O6	178.48 (12)	C8—C9—C10—C4	178.62 (12)
C51—C5—C6—O6	−4.21 (19)	O1—C9—C10—C4	−6.98 (19)
C10—C5—C6—C7	−2.1 (2)	C6—C5—C10—C9	3.79 (19)
C51—C5—C6—C7	175.21 (14)	C51—C5—C10—C9	−173.32 (14)
O6—C6—C7—C8	178.97 (12)	C6—C5—C10—C4	−178.36 (12)
C5—C6—C7—C8	−0.42 (18)	C51—C5—C10—C4	4.5 (2)
O6—C6—C7—C71	0.76 (18)	C41—C4—C10—C9	−145.20 (17)
C5—C6—C7—C71	−178.63 (12)	C3—C4—C10—C9	−29.13 (18)
C6—C7—C8—C9	1.04 (18)	C42—C4—C10—C9	89.17 (17)
C71—C7—C8—C9	179.19 (12)	C41—C4—C10—C5	37.0 (2)
C6—C7—C8—C81	−179.32 (13)	C3—C4—C10—C5	153.03 (15)
C71—C7—C8—C81	−1.2 (2)	C42—C4—C10—C5	−88.67 (19)
C7—C8—C9—C10	0.9 (2)

(cum222) 6-hyroxy-4,4,5,7,8-pentamathyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1276.9 (3) Å^3
Mr = 234.28	Z = 4
P21/n, monoclinic	F(000) = 504
a = 13.344 (2) Å	Dx = 1.219 Mg m^−3
b = 6.854 (1) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.964 (2) Å	µ = 0.08 mm^−1
α = 90°	T = 220 K
β = 91.18 (2)°	, colourlees
γ = 90°	0.44 × 0.38 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 29.6°, θmin = 3.3°
5901 measured reflections	h = −16→15
2966 independent reflections	k = −9→9
1256 reflections with I > 2σ(I)	l = −18→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.226	w = 1/[σ^2(Fo^2) + (0.1493P)^2 + 0.1P] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max = 0.099
2966 reflections	Δρmax = 0.50 e Å^−3
227 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.001 (2)

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	0.79796 (13)	0.2117 (3)	−0.30463 (11)	0.0434 (5)
O6	1.16002 (14)	0.2499 (2)	−0.48383 (14)	0.0462 (5)
H6	1.161 (3)	0.268 (6)	−0.553 (3)	0.123 (16)*
O2	0.70231 (17)	0.2098 (3)	−0.18039 (15)	0.0679 (7)
C2	0.7841 (2)	0.2472 (4)	−0.21136 (19)	0.0472 (7)
C3	0.8710 (2)	0.3324 (5)	−0.1580 (2)	0.0549 (8)
H3A	0.858 (2)	0.321 (4)	−0.090 (2)	0.069 (9)*
H3B	0.8742 (19)	0.475 (4)	−0.1779 (18)	0.055 (8)*
C4	0.9707 (2)	0.2317 (4)	−0.18134 (17)	0.0460 (7)
C41	1.0503 (3)	0.3466 (8)	−0.1242 (3)	0.0771 (12)
H41A	1.021 (3)	0.377 (5)	−0.068 (3)	0.095 (12)*
H41B	1.062 (2)	0.474 (4)	−0.1570 (19)	0.052 (9)*
H41C	1.113 (3)	0.271 (5)	−0.123 (3)	0.094 (14)*
C42	0.9678 (4)	0.0183 (6)	−0.1468 (3)	0.0735 (11)
H42A	0.956 (2)	0.011 (5)	−0.078 (2)	0.090 (11)*
H42B	1.038 (3)	−0.043 (5)	−0.154 (2)	0.089 (11)*
H42C	0.914 (2)	−0.067 (4)	−0.186 (2)	0.066 (9)*
C5	1.07135 (19)	0.2360 (3)	−0.33939 (17)	0.0359 (6)
C51	1.1743 (2)	0.2151 (6)	−0.2920 (2)	0.0556 (8)
H51A	1.214 (3)	0.169 (5)	−0.340 (3)	0.097 (12)*
H51B	1.173 (2)	0.126 (4)	−0.235 (2)	0.067 (9)*
H51C	1.197 (3)	0.337 (5)	−0.267 (2)	0.083 (11)*
C6	1.06876 (18)	0.2466 (3)	−0.44038 (17)	0.0341 (6)
C7	0.97902 (19)	0.2520 (3)	−0.49366 (16)	0.0323 (6)
C71	0.9827 (3)	0.2597 (4)	−0.60184 (18)	0.0422 (7)
H71A	1.020 (2)	0.158 (5)	−0.624 (2)	0.066 (9)*
H71B	1.017 (2)	0.376 (4)	−0.6191 (18)	0.058 (8)*
H71C	0.910 (4)	0.252 (5)	−0.631 (3)	0.100 (14)*
C8	0.88896 (18)	0.2458 (3)	−0.44596 (16)	0.0332 (6)
C81	0.7890 (2)	0.2493 (5)	−0.4975 (2)	0.0455 (7)
H81A	0.787 (3)	0.347 (5)	−0.546 (2)	0.090 (11)*
H81B	0.736 (3)	0.277 (5)	−0.455 (3)	0.109 (14)*
H81C	0.778 (3)	0.133 (5)	−0.531 (2)	0.090 (12)*
C9	0.89256 (18)	0.2372 (3)	−0.34578 (16)	0.0330 (6)
C10	0.98129 (19)	0.2369 (3)	−0.29080 (16)	0.0351 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0324 (11)	0.0629 (12)	0.0354 (9)	−0.0016 (8)	0.0090 (7)	−0.0008 (8)
O6	0.0336 (12)	0.0552 (11)	0.0503 (11)	0.0026 (8)	0.0115 (8)	0.0005 (8)
O2	0.0537 (15)	0.0955 (17)	0.0556 (12)	−0.0081 (12)	0.0261 (10)	−0.0046 (10)
C2	0.0428 (19)	0.0579 (17)	0.0416 (14)	0.0060 (13)	0.0186 (12)	0.0019 (11)
C3	0.053 (2)	0.074 (2)	0.0385 (15)	0.0039 (16)	0.0088 (13)	−0.0086 (15)
C4	0.0424 (18)	0.0639 (17)	0.0316 (12)	0.0054 (13)	0.0016 (11)	−0.0035 (11)
C41	0.065 (3)	0.113 (4)	0.052 (2)	0.009 (2)	−0.0074 (17)	−0.033 (2)
C42	0.091 (3)	0.082 (2)	0.0480 (18)	0.018 (2)	0.0084 (19)	0.0160 (17)
C5	0.0334 (16)	0.0331 (12)	0.0413 (13)	0.0006 (10)	0.0017 (10)	−0.0037 (9)
C51	0.041 (2)	0.073 (2)	0.0526 (18)	0.0060 (15)	−0.0055 (14)	−0.0060 (16)
C6	0.0292 (15)	0.0321 (12)	0.0414 (12)	0.0003 (10)	0.0099 (10)	−0.0022 (9)
C7	0.0365 (15)	0.0279 (11)	0.0328 (11)	−0.0001 (10)	0.0049 (9)	−0.0023 (9)
C71	0.049 (2)	0.0438 (16)	0.0342 (12)	0.0007 (13)	0.0129 (12)	−0.0015 (11)
C8	0.0344 (15)	0.0316 (12)	0.0335 (12)	−0.0017 (10)	0.0017 (9)	−0.0009 (9)
C81	0.0388 (18)	0.0575 (18)	0.0401 (14)	−0.0008 (13)	−0.0008 (12)	−0.0011 (13)
C9	0.0295 (14)	0.0356 (12)	0.0343 (12)	−0.0006 (10)	0.0077 (9)	−0.0010 (9)
C10	0.0354 (15)	0.0373 (12)	0.0328 (11)	0.0004 (10)	0.0012 (10)	−0.0014 (9)

Geometric parameters (Å, º)

O1—C2	1.341 (3)	C5—C10	1.392 (3)
O1—C9	1.408 (3)	C5—C6	1.412 (3)
O6—C6	1.372 (3)	C5—C51	1.520 (4)
O2—C2	1.210 (3)	C6—C7	1.397 (4)
C2—C3	1.485 (4)	C7—C8	1.387 (3)
C3—C4	1.540 (4)	C7—C71	1.513 (3)
C4—C41	1.534 (5)	C8—C9	1.400 (3)
C4—C10	1.538 (3)	C8—C81	1.502 (4)
C4—C42	1.541 (4)	C9—C10	1.398 (4)
C2—O1—C9	121.1 (2)	O6—C6—C5	116.0 (2)
O2—C2—O1	116.9 (3)	C7—C6—C5	122.4 (2)
O2—C2—C3	127.2 (2)	C8—C7—C6	119.0 (2)
O1—C2—C3	115.9 (2)	C8—C7—C71	121.8 (2)
C2—C3—C4	112.7 (2)	C6—C7—C71	119.2 (2)
C41—C4—C10	115.4 (3)	C7—C8—C9	118.0 (2)
C41—C4—C3	104.6 (3)	C7—C8—C81	122.6 (2)
C10—C4—C3	107.3 (2)	C9—C8—C81	119.4 (2)
C41—C4—C42	110.3 (3)	C8—C9—C10	124.1 (2)
C10—C4—C42	109.7 (2)	C8—C9—O1	113.6 (2)
C3—C4—C42	109.4 (3)	C10—C9—O1	122.1 (2)
C10—C5—C6	118.9 (2)	C5—C10—C9	117.5 (2)
C10—C5—C51	124.8 (2)	C5—C10—C4	125.6 (2)
C6—C5—C51	116.3 (2)	C9—C10—C4	116.8 (2)
O6—C6—C7	121.5 (2)
C9—O1—C2—O2	−175.4 (2)	C81—C8—C9—C10	−178.8 (2)
C9—O1—C2—C3	5.8 (3)	C7—C8—C9—O1	−173.98 (18)
O2—C2—C3—C4	137.0 (3)	C81—C8—C9—O1	6.4 (3)
O1—C2—C3—C4	−44.4 (3)	C2—O1—C9—C8	−163.7 (2)
C2—C3—C4—C41	177.0 (3)	C2—O1—C9—C10	21.4 (3)
C2—C3—C4—C10	54.0 (3)	C6—C5—C10—C9	3.5 (3)
C2—C3—C4—C42	−64.9 (3)	C51—C5—C10—C9	−173.6 (3)
C10—C5—C6—O6	178.5 (2)	C6—C5—C10—C4	−178.3 (2)
C51—C5—C6—O6	−4.2 (3)	C51—C5—C10—C4	4.6 (4)
C10—C5—C6—C7	−2.0 (3)	C8—C9—C10—C5	−3.1 (3)
C51—C5—C6—C7	175.3 (2)	O1—C9—C10—C5	171.3 (2)
O6—C6—C7—C8	179.20 (19)	C8—C9—C10—C4	178.6 (2)
C5—C6—C7—C8	−0.3 (3)	O1—C9—C10—C4	−7.0 (3)
O6—C6—C7—C71	0.6 (3)	C41—C4—C10—C5	36.7 (4)
C5—C6—C7—C71	−178.9 (2)	C3—C4—C10—C5	152.7 (2)
C6—C7—C8—C9	0.9 (3)	C42—C4—C10—C5	−88.6 (3)
C71—C7—C8—C9	179.4 (2)	C41—C4—C10—C9	−145.1 (3)
C6—C7—C8—C81	−179.5 (2)	C3—C4—C10—C9	−29.1 (3)
C71—C7—C8—C81	−0.9 (3)	C42—C4—C10—C9	89.6 (3)
C7—C8—C9—C10	0.8 (3)

(cum224) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1277.6 (3) Å^3
Mr = 234.28	Z = 4
P21/n, monoclinic	F(000) = 504
a = 13.341 (2) Å	Dx = 1.218 Mg m^−3
b = 6.857 (1) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.969 (2) Å	µ = 0.08 mm^−1
α = 90°	T = 224 K
β = 91.18 (2)°	, colourlees
γ = 90°	0.44 × 0.38 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 29.6°, θmin = 3.3°
6101 measured reflections	h = −15→16
2984 independent reflections	k = −9→9
964 reflections with I > 2σ(I)	l = −14→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.188	w = 1/[σ^2(Fo^2) + (0.078P)^2 + 0.099P] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
2984 reflections	Δρmax = 0.40 e Å^−3
227 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (16)

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	0.79833 (14)	0.2123 (3)	−0.30442 (13)	0.0458 (6)
O6	1.15996 (14)	0.2499 (3)	−0.48387 (15)	0.0490 (6)
H6	1.162 (2)	0.266 (4)	−0.557 (2)	0.076 (11)*
O2	0.70221 (18)	0.2113 (4)	−0.18018 (16)	0.0721 (8)
C2	0.7841 (2)	0.2468 (4)	−0.2112 (2)	0.0497 (8)
C3	0.8713 (3)	0.3321 (6)	−0.1580 (2)	0.0580 (10)
H3A	0.854 (2)	0.321 (4)	−0.091 (2)	0.071 (10)*
H3B	0.883 (2)	0.480 (5)	−0.180 (2)	0.071 (10)*
C4	0.9707 (2)	0.2322 (4)	−0.18200 (19)	0.0482 (8)
C41	1.0504 (4)	0.3465 (9)	−0.1243 (3)	0.0830 (14)
H41A	1.023 (3)	0.369 (5)	−0.067 (3)	0.084 (12)*
H41B	1.063 (2)	0.476 (4)	−0.1538 (19)	0.048 (10)*
H41C	1.117 (4)	0.262 (6)	−0.122 (4)	0.15 (2)*
C42	0.9682 (4)	0.0172 (7)	−0.1470 (3)	0.0823 (14)
H42A	0.957 (3)	0.009 (5)	−0.078 (3)	0.110 (14)*
H42B	1.039 (3)	−0.036 (6)	−0.160 (2)	0.102 (14)*
H42C	0.911 (3)	−0.070 (6)	−0.191 (3)	0.123 (16)*
C5	1.0713 (2)	0.2370 (4)	−0.33965 (19)	0.0374 (7)
C51	1.1745 (3)	0.2175 (7)	−0.2926 (3)	0.0593 (10)
H51A	1.214 (3)	0.155 (6)	−0.344 (3)	0.130 (16)*
H51B	1.175 (2)	0.118 (4)	−0.237 (2)	0.061 (10)*
H51C	1.202 (3)	0.343 (6)	−0.269 (3)	0.122 (17)*
C6	1.0687 (2)	0.2470 (4)	−0.44012 (18)	0.0343 (6)
C7	0.9792 (2)	0.2519 (4)	−0.49352 (18)	0.0354 (7)
C71	0.9818 (3)	0.2591 (5)	−0.6018 (2)	0.0454 (8)
H71A	1.021 (2)	0.157 (4)	−0.626 (2)	0.062 (10)*
H71B	1.021 (2)	0.374 (4)	−0.6195 (19)	0.065 (10)*
H71C	0.908 (3)	0.265 (5)	−0.632 (3)	0.107 (14)*
C8	0.8889 (2)	0.2459 (4)	−0.44592 (17)	0.0345 (6)
C81	0.7888 (2)	0.2491 (6)	−0.4975 (2)	0.0481 (8)
H81A	0.784 (3)	0.352 (5)	−0.542 (3)	0.106 (14)*
H81B	0.732 (4)	0.279 (6)	−0.451 (4)	0.153 (19)*
H81C	0.775 (3)	0.132 (6)	−0.533 (3)	0.129 (17)*
C9	0.8929 (2)	0.2380 (4)	−0.34588 (18)	0.0350 (7)
C10	0.9814 (2)	0.2380 (4)	−0.29090 (18)	0.0368 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0376 (13)	0.0642 (14)	0.0361 (10)	−0.0032 (10)	0.0109 (8)	−0.0016 (10)
O6	0.0379 (13)	0.0570 (13)	0.0527 (13)	0.0025 (11)	0.0147 (10)	0.0016 (11)
O2	0.0568 (17)	0.1007 (19)	0.0600 (14)	−0.0079 (14)	0.0278 (12)	−0.0062 (13)
C2	0.047 (2)	0.061 (2)	0.0417 (17)	0.0111 (18)	0.0186 (15)	0.0022 (16)
C3	0.053 (2)	0.085 (3)	0.0368 (19)	0.0013 (19)	0.0048 (16)	−0.0100 (19)
C4	0.046 (2)	0.062 (2)	0.0368 (16)	0.0078 (17)	0.0005 (13)	−0.0047 (16)
C41	0.075 (3)	0.117 (4)	0.056 (3)	0.005 (3)	−0.006 (2)	−0.029 (3)
C42	0.105 (4)	0.091 (3)	0.051 (2)	0.021 (3)	0.016 (2)	0.022 (2)
C5	0.0324 (18)	0.0375 (16)	0.0423 (16)	0.0014 (13)	0.0006 (12)	−0.0023 (13)
C51	0.046 (2)	0.075 (3)	0.056 (2)	0.007 (2)	−0.0039 (17)	0.001 (2)
C6	0.0318 (17)	0.0294 (15)	0.0420 (15)	0.0013 (13)	0.0089 (12)	−0.0011 (13)
C7	0.0412 (18)	0.0310 (14)	0.0343 (14)	0.0006 (15)	0.0060 (12)	−0.0024 (12)
C71	0.051 (2)	0.048 (2)	0.0378 (16)	0.003 (2)	0.0137 (15)	−0.0004 (15)
C8	0.0359 (17)	0.0320 (15)	0.0357 (15)	−0.0016 (13)	0.0022 (11)	−0.0001 (13)
C81	0.043 (2)	0.058 (2)	0.0427 (18)	0.0028 (19)	−0.0049 (14)	0.0036 (19)
C9	0.0336 (17)	0.0363 (15)	0.0355 (14)	−0.0021 (14)	0.0087 (12)	−0.0004 (13)
C10	0.0354 (18)	0.0391 (16)	0.0359 (15)	0.0016 (14)	0.0024 (12)	−0.0006 (13)

Geometric parameters (Å, º)

O1—C2	1.341 (3)	C5—C10	1.392 (4)
O1—C9	1.411 (3)	C5—C6	1.405 (4)
O6—C6	1.374 (3)	C5—C51	1.519 (4)
O2—C2	1.208 (3)	C6—C7	1.395 (4)
C2—C3	1.488 (5)	C7—C8	1.389 (4)
C3—C4	1.536 (4)	C7—C71	1.514 (4)
C4—C10	1.531 (4)	C8—C9	1.399 (3)
C4—C41	1.536 (5)	C8—C81	1.505 (4)
C4—C42	1.553 (5)	C9—C10	1.394 (4)
C2—O1—C9	121.5 (2)	O6—C6—C5	116.1 (2)
O2—C2—O1	117.4 (3)	C7—C6—C5	122.6 (2)
O2—C2—C3	127.1 (3)	C8—C7—C6	119.0 (2)
O1—C2—C3	115.4 (3)	C8—C7—C71	121.2 (3)
C2—C3—C4	112.7 (3)	C6—C7—C71	119.9 (3)
C10—C4—C41	115.5 (3)	C7—C8—C9	117.6 (2)
C10—C4—C3	107.6 (2)	C7—C8—C81	122.7 (2)
C41—C4—C3	104.4 (3)	C9—C8—C81	119.7 (3)
C10—C4—C42	109.9 (3)	C10—C9—C8	124.4 (2)
C41—C4—C42	109.8 (4)	C10—C9—O1	121.9 (2)
C3—C4—C42	109.3 (3)	C8—C9—O1	113.5 (2)
C10—C5—C6	119.0 (2)	C5—C10—C9	117.3 (2)
C10—C5—C51	124.8 (3)	C5—C10—C4	125.7 (2)
C6—C5—C51	116.2 (3)	C9—C10—C4	116.9 (2)
O6—C6—C7	121.2 (2)
C9—O1—C2—O2	−176.1 (2)	C81—C8—C9—C10	−178.8 (3)
C9—O1—C2—C3	5.9 (4)	C7—C8—C9—O1	−173.9 (2)
O2—C2—C3—C4	138.0 (3)	C81—C8—C9—O1	6.5 (4)
O1—C2—C3—C4	−44.3 (4)	C2—O1—C9—C10	21.1 (4)
C2—C3—C4—C10	54.1 (4)	C2—O1—C9—C8	−164.1 (3)
C2—C3—C4—C41	177.4 (3)	C6—C5—C10—C9	3.5 (4)
C2—C3—C4—C42	−65.2 (4)	C51—C5—C10—C9	−173.9 (3)
C10—C5—C6—O6	178.6 (2)	C6—C5—C10—C4	−178.7 (3)
C51—C5—C6—O6	−3.7 (4)	C51—C5—C10—C4	3.9 (5)
C10—C5—C6—C7	−2.1 (4)	C8—C9—C10—C5	−3.0 (4)
C51—C5—C6—C7	175.6 (3)	O1—C9—C10—C5	171.2 (2)
O6—C6—C7—C8	179.1 (2)	C8—C9—C10—C4	179.0 (2)
C5—C6—C7—C8	−0.2 (4)	O1—C9—C10—C4	−6.8 (4)
O6—C6—C7—C71	0.4 (4)	C41—C4—C10—C5	36.8 (5)
C5—C6—C7—C71	−178.9 (3)	C3—C4—C10—C5	153.0 (3)
C6—C7—C8—C9	0.9 (4)	C42—C4—C10—C5	−88.1 (4)
C71—C7—C8—C9	179.5 (3)	C41—C4—C10—C9	−145.4 (3)
C6—C7—C8—C81	−179.6 (3)	C3—C4—C10—C9	−29.2 (4)
C71—C7—C8—C81	−0.9 (4)	C42—C4—C10—C9	89.7 (4)
C7—C8—C9—C10	0.8 (4)

(cum225c) 6-hydroxhy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1275.8 (10) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.760 (7) Å	Dx = 1.220 Mg m^−3
b = 6.863 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.113 (4) Å	µ = 0.09 mm^−1
α = 90°	T = 225 K
β = 94.75 (4)°	, colourlees
γ = 90°	0.30 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 29.5°, θmin = 3.6°
7747 measured reflections	h = −13→13
3276 independent reflections	k = −9→5
955 reflections with I > 2σ(I)	l = −26→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.012P)^2 + 0.093P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.003
3276 reflections	Δρmax = 0.25 e Å^−3
216 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0116 (5)

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	0.10284 (13)	0.2346 (2)	0.24735 (7)	0.0432 (4)
O2	−0.11655 (16)	0.2357 (3)	0.26180 (9)	0.0735 (6)
O6	0.65080 (13)	0.2618 (3)	0.33863 (8)	0.0463 (5)
H6	0.711 (2)	0.253 (4)	0.3040 (10)	0.065*
C2	−0.0016 (3)	0.2707 (4)	0.28681 (14)	0.0489 (7)
C3	0.0369 (3)	0.3631 (4)	0.35565 (15)	0.0542 (8)
H3A	−0.050 (2)	0.359 (3)	0.3852 (11)	0.076*
H3B	0.073 (2)	0.513 (3)	0.3462 (11)	0.076*
C4	0.1646 (2)	0.2689 (4)	0.39527 (12)	0.0469 (7)
C41	0.1961 (4)	0.3998 (6)	0.46048 (17)	0.0951 (14)
H41A	0.107 (3)	0.405 (4)	0.4821 (15)	0.133*
H41B	0.226 (3)	0.535 (4)	0.4466 (16)	0.133*
H41C	0.260 (3)	0.335 (4)	0.4968 (15)	0.133*
C42	0.1287 (4)	0.0598 (6)	0.4171 (2)	0.0931 (12)
H42A	0.218 (3)	−0.011 (4)	0.4438 (14)	0.130*
H42B	0.106 (3)	−0.022 (4)	0.3670 (15)	0.130*
H42C	0.058 (3)	0.072 (4)	0.4459 (14)	0.130*
C5	0.4206 (2)	0.2584 (3)	0.36639 (11)	0.0327 (6)
C51	0.4806 (3)	0.2385 (5)	0.44137 (13)	0.0553 (8)
H51A	0.419 (2)	0.158 (3)	0.4715 (12)	0.083*
H51B	0.498 (2)	0.370 (4)	0.4661 (11)	0.083*
H51C	0.581 (2)	0.178 (3)	0.4432 (11)	0.083*
C6	0.5135 (2)	0.2621 (3)	0.31470 (11)	0.0305 (6)
C7	0.47309 (19)	0.2658 (3)	0.24311 (11)	0.0296 (5)
C71	0.5795 (3)	0.2682 (5)	0.19065 (16)	0.0436 (7)
H71A	0.544 (2)	0.277 (3)	0.1408 (12)	0.075 (9)*
H71B	0.639 (3)	0.156 (4)	0.1938 (13)	0.094 (11)*
H71C	0.651 (2)	0.367 (3)	0.2007 (12)	0.081 (10)*
C8	0.33261 (19)	0.2612 (3)	0.22211 (10)	0.0289 (5)
C81	0.2798 (3)	0.2582 (6)	0.14532 (14)	0.0459 (7)
H81A	0.308 (3)	0.135 (5)	0.1218 (14)	0.130 (14)*
H81B	0.317 (2)	0.354 (4)	0.1216 (12)	0.080 (12)*
H81C	0.173 (3)	0.256 (4)	0.1410 (13)	0.121 (11)*
C9	0.24245 (19)	0.2597 (3)	0.27472 (11)	0.0308 (6)
C10	0.2798 (2)	0.2632 (3)	0.34630 (11)	0.0327 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0227 (8)	0.0618 (11)	0.0453 (10)	−0.0032 (10)	0.0041 (8)	−0.0036 (11)
O2	0.0238 (9)	0.1023 (15)	0.0946 (14)	−0.0046 (13)	0.0064 (10)	−0.0120 (14)
O6	0.0273 (10)	0.0528 (11)	0.0575 (11)	0.0006 (11)	−0.0032 (8)	−0.0013 (12)
C2	0.0347 (15)	0.0564 (19)	0.0570 (18)	0.0049 (18)	0.0128 (14)	0.0045 (19)
C3	0.0336 (16)	0.085 (2)	0.0459 (19)	0.0085 (16)	0.0117 (15)	0.0001 (17)
C4	0.0401 (15)	0.062 (2)	0.0404 (15)	0.0074 (17)	0.0142 (13)	0.0081 (18)
C41	0.075 (3)	0.162 (4)	0.050 (2)	0.042 (3)	0.010 (2)	−0.026 (3)
C42	0.074 (2)	0.098 (3)	0.114 (3)	0.015 (2)	0.049 (2)	0.052 (2)
C5	0.0330 (13)	0.0327 (14)	0.0319 (13)	0.0025 (15)	−0.0005 (11)	−0.0015 (16)
C51	0.0525 (17)	0.068 (2)	0.0439 (18)	0.0034 (19)	−0.0047 (14)	−0.0040 (19)
C6	0.0248 (13)	0.0196 (13)	0.0462 (15)	0.0002 (14)	−0.0027 (11)	−0.0027 (15)
C7	0.0271 (13)	0.0230 (13)	0.0397 (15)	0.0019 (14)	0.0087 (11)	0.0005 (15)
C71	0.0321 (15)	0.046 (2)	0.0544 (19)	−0.0001 (18)	0.0152 (14)	−0.001 (2)
C8	0.0295 (12)	0.0254 (14)	0.0319 (14)	−0.0024 (14)	0.0018 (11)	−0.0016 (15)
C81	0.0479 (18)	0.055 (2)	0.0351 (16)	−0.008 (2)	0.0058 (14)	−0.002 (2)
C9	0.0184 (12)	0.0330 (14)	0.0410 (14)	−0.0006 (14)	0.0021 (10)	0.0014 (16)
C10	0.0310 (13)	0.0374 (15)	0.0299 (13)	−0.0003 (15)	0.0037 (11)	0.0032 (15)

Geometric parameters (Å, º)

O1—C2	1.341 (2)	C5—C6	1.396 (3)
O1—C9	1.429 (2)	C5—C10	1.396 (3)
O2—C2	1.206 (3)	C5—C51	1.509 (3)
O6—C6	1.380 (2)	C51—H51A	1.03 (2)
O6—H6	0.92 (2)	C51—H51B	1.03 (2)
C2—C3	1.480 (3)	C51—H51C	1.06 (2)
C3—C4	1.546 (3)	C6—C7	1.393 (2)
C3—H3A	1.06 (2)	C7—C8	1.397 (3)
C3—H3B	1.11 (2)	C7—C71	1.502 (3)
C4—C10	1.521 (3)	C71—H71A	0.99 (2)
C4—C42	1.544 (4)	C71—H71B	0.96 (2)
C4—C41	1.546 (4)	C71—H71C	0.98 (2)
C41—H41A	1.00 (3)	C8—C9	1.390 (2)
C41—H41B	1.02 (3)	C8—C81	1.515 (3)
C41—H41C	1.00 (3)	C81—H81A	1.00 (3)
C42—H42A	1.09 (3)	C81—H81B	0.89 (2)
C42—H42B	1.12 (3)	C81—H81C	1.04 (2)
C42—H42C	0.92 (3)	C9—C10	1.387 (2)
C2—O1—C9	121.21 (18)	C5—C51—H51B	113.2 (13)
C6—O6—H6	114.9 (14)	H51A—C51—H51B	107.2 (19)
O2—C2—O1	117.7 (2)	C5—C51—H51C	110.5 (12)
O2—C2—C3	126.6 (2)	H51A—C51—H51C	110.5 (18)
O1—C2—C3	115.5 (2)	H51B—C51—H51C	102.3 (18)
C2—C3—C4	113.0 (2)	O6—C6—C7	120.9 (2)
C2—C3—H3A	107.9 (11)	O6—C6—C5	115.8 (2)
C4—C3—H3A	112.3 (11)	C7—C6—C5	123.2 (2)
C2—C3—H3B	108.2 (11)	C6—C7—C8	118.2 (2)
C4—C3—H3B	102.5 (12)	C6—C7—C71	120.1 (2)
H3A—C3—H3B	112.8 (18)	C8—C7—C71	121.7 (2)
C10—C4—C42	109.8 (2)	C7—C71—H71A	115.9 (13)
C10—C4—C3	108.45 (19)	C7—C71—H71B	113.3 (16)
C42—C4—C3	109.2 (2)	H71A—C71—H71B	106 (2)
C10—C4—C41	113.8 (2)	C7—C71—H71C	113.3 (15)
C42—C4—C41	110.9 (3)	H71A—C71—H71C	109 (2)
C3—C4—C41	104.5 (2)	H71B—C71—H71C	97.2 (17)
C4—C41—H41A	103.4 (17)	C9—C8—C7	117.2 (2)
C4—C41—H41B	111.3 (18)	C9—C8—C81	121.0 (2)
H41A—C41—H41B	111 (3)	C7—C8—C81	121.7 (2)
C4—C41—H41C	111.9 (18)	C8—C81—H81A	111.3 (16)
H41A—C41—H41C	104 (2)	C8—C81—H81B	111.1 (16)
H41B—C41—H41C	114 (3)	H81A—C81—H81B	105 (2)
C4—C42—H42A	110.6 (15)	C8—C81—H81C	109.6 (14)
C4—C42—H42B	105.6 (16)	H81A—C81—H81C	105 (2)
H42A—C42—H42B	106 (2)	H81B—C81—H81C	115 (2)
C4—C42—H42C	106 (2)	C10—C9—C8	125.69 (19)
H42A—C42—H42C	112 (2)	C10—C9—O1	121.86 (19)
H42B—C42—H42C	117 (3)	C8—C9—O1	112.19 (18)
C6—C5—C10	119.2 (2)	C9—C10—C5	116.3 (2)
C6—C5—C51	116.7 (2)	C9—C10—C4	117.41 (19)
C10—C5—C51	124.0 (2)	C5—C10—C4	126.3 (2)
C5—C51—H51A	112.6 (13)
C9—O1—C2—O2	−175.8 (3)	C81—C8—C9—C10	−179.6 (3)
C9—O1—C2—C3	8.2 (3)	C7—C8—C9—O1	−173.9 (2)
O2—C2—C3—C4	139.7 (3)	C81—C8—C9—O1	6.2 (4)
O1—C2—C3—C4	−44.7 (3)	C2—O1—C9—C10	20.1 (3)
C2—C3—C4—C10	52.1 (3)	C2—O1—C9—C8	−165.4 (2)
C2—C3—C4—C42	−67.5 (3)	C8—C9—C10—C5	−3.2 (4)
C2—C3—C4—C41	173.9 (2)	O1—C9—C10—C5	170.4 (2)
C10—C5—C6—O6	178.5 (2)	C8—C9—C10—C4	177.6 (2)
C51—C5—C6—O6	−4.7 (3)	O1—C9—C10—C4	−8.7 (4)
C10—C5—C6—C7	−1.6 (4)	C6—C5—C10—C9	3.7 (4)
C51—C5—C6—C7	175.3 (2)	C51—C5—C10—C9	−172.9 (3)
O6—C6—C7—C8	178.5 (2)	C6—C5—C10—C4	−177.2 (2)
C5—C6—C7—C8	−1.5 (4)	C51—C5—C10—C4	6.2 (4)
O6—C6—C7—C71	0.4 (4)	C42—C4—C10—C9	93.3 (3)
C5—C6—C7—C71	−179.6 (2)	C3—C4—C10—C9	−25.9 (3)
C6—C7—C8—C9	2.1 (4)	C41—C4—C10—C9	−141.8 (3)
C71—C7—C8—C9	−179.9 (3)	C42—C4—C10—C5	−85.8 (3)
C6—C7—C8—C81	−178.0 (3)	C3—C4—C10—C5	155.0 (3)
C71—C7—C8—C81	0.0 (4)	C41—C4—C10—C5	39.2 (4)
C7—C8—C9—C10	0.3 (4)

(cum230) 6-hydroxy-4,4,5,7,8-pentamathyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1279.6 (2) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.758 (1) Å	Dx = 1.216 Mg m^−3
b = 6.883 (1) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.117 (1) Å	µ = 0.08 mm^−1
α = 90°	T = 230 K
β = 94.75 (1)°	, colourlees
γ = 90°	0.44 × 0.38 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 29.6°, θmin = 3.7°
7607 measured reflections	h = −6→13
3249 independent reflections	k = −9→9
1648 reflections with I > 2σ(I)	l = −25→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.216	w = 1/[σ^2(Fo^2) + (0.1275P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 2.962
3249 reflections	Δρmax = 0.40 e Å^−3
232 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.000 (6)

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)
O1	0.10309 (13)	0.23474 (19)	0.24743 (7)	0.0436 (4)
O2	−0.11600 (16)	0.2348 (3)	0.26197 (11)	0.0729 (6)
O6	0.65074 (14)	0.26179 (19)	0.33880 (9)	0.0456 (4)
H6	0.713 (3)	0.252 (3)	0.3033 (17)	0.081 (9)*
C2	−0.0015 (2)	0.2719 (3)	0.28711 (13)	0.0488 (6)
C3	0.0379 (2)	0.3627 (4)	0.35639 (13)	0.0552 (7)	0.99
H3A	−0.045 (3)	0.351 (4)	0.3837 (14)	0.079 (8)*	0.99
H3B	0.056 (2)	0.494 (4)	0.3473 (13)	0.068 (8)*	0.99
C3'	0.037 (9)	0.144 (13)	0.356 (5)	0.000 (16)*	0.01
C4	0.1644 (2)	0.2684 (3)	0.39596 (11)	0.0491 (6)
C41	0.1971 (4)	0.4010 (7)	0.46021 (16)	0.0943 (13)
H41A	0.106 (3)	0.410 (4)	0.4806 (14)	0.090 (8)*
H41B	0.230 (5)	0.534 (7)	0.447 (3)	0.20 (3)*
H41C	0.258 (4)	0.311 (5)	0.499 (2)	0.111 (11)*
C42	0.1277 (3)	0.0584 (6)	0.4159 (2)	0.0918 (12)
H42A	0.050 (3)	0.068 (4)	0.4461 (16)	0.102 (10)*
H42B	0.208 (3)	0.014 (4)	0.4468 (15)	0.094 (9)*
H42C	0.100 (5)	−0.028 (7)	0.367 (3)	0.179 (19)*
C5	0.42090 (19)	0.2590 (2)	0.36647 (10)	0.0338 (4)
C51	0.4819 (3)	0.2403 (4)	0.44171 (12)	0.0536 (6)
H51A	0.425 (3)	0.144 (4)	0.4663 (15)	0.092 (9)*
H51B	0.507 (4)	0.363 (5)	0.4591 (19)	0.128 (13)*
H51C	0.574 (4)	0.187 (5)	0.4406 (16)	0.098 (10)*
C6	0.51452 (17)	0.2632 (2)	0.31477 (10)	0.0329 (4)
C7	0.47264 (17)	0.2663 (2)	0.24286 (10)	0.0307 (4)
C71	0.5801 (2)	0.2682 (3)	0.19032 (12)	0.0416 (5)
H71A	0.534 (3)	0.283 (4)	0.1425 (18)	0.094 (10)*
H71B	0.638 (2)	0.155 (4)	0.1918 (11)	0.063 (7)*
H71C	0.649 (3)	0.373 (4)	0.1983 (12)	0.068 (7)*
C8	0.33320 (18)	0.2620 (2)	0.22171 (9)	0.0307 (4)
C81	0.2790 (2)	0.2600 (3)	0.14553 (11)	0.0439 (5)
H81A	0.306 (3)	0.143 (4)	0.1227 (15)	0.089 (9)*
H81B	0.319 (3)	0.371 (5)	0.1201 (17)	0.120 (12)*
H81C	0.180 (4)	0.280 (4)	0.1377 (18)	0.107 (11)*
C9	0.24049 (18)	0.2592 (2)	0.27410 (10)	0.0316 (4)
C10	0.28022 (19)	0.2636 (2)	0.34596 (10)	0.0334 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (7)	0.0634 (9)	0.0456 (8)	−0.0028 (5)	0.0030 (6)	−0.0033 (6)
O2	0.0249 (8)	0.1037 (15)	0.0907 (14)	−0.0037 (7)	0.0077 (8)	−0.0136 (10)
O6	0.0257 (7)	0.0534 (9)	0.0567 (9)	0.0008 (5)	−0.0035 (6)	−0.0047 (6)
C2	0.0239 (9)	0.0589 (13)	0.0645 (14)	0.0023 (8)	0.0097 (9)	0.0033 (10)
C3	0.0395 (12)	0.0706 (18)	0.0574 (14)	0.0114 (11)	0.0164 (10)	0.0014 (13)
C4	0.0418 (12)	0.0684 (15)	0.0392 (11)	0.0097 (9)	0.0149 (9)	0.0069 (10)
C41	0.073 (2)	0.160 (4)	0.0504 (16)	0.050 (2)	0.0103 (14)	−0.024 (2)
C42	0.0639 (18)	0.112 (3)	0.105 (3)	0.0120 (17)	0.0379 (19)	0.058 (2)
C5	0.0332 (10)	0.0319 (10)	0.0359 (10)	0.0029 (7)	−0.0004 (7)	−0.0009 (7)
C51	0.0499 (14)	0.0700 (17)	0.0392 (12)	0.0081 (12)	−0.0063 (10)	−0.0021 (11)
C6	0.0244 (9)	0.0300 (9)	0.0439 (10)	0.0009 (6)	0.0000 (7)	−0.0023 (7)
C7	0.0257 (9)	0.0282 (9)	0.0390 (10)	−0.0016 (6)	0.0067 (7)	−0.0014 (7)
C71	0.0306 (10)	0.0430 (12)	0.0533 (13)	0.0007 (8)	0.0149 (9)	0.0026 (9)
C8	0.0291 (9)	0.0305 (9)	0.0328 (9)	−0.0002 (6)	0.0042 (7)	0.0000 (7)
C81	0.0410 (12)	0.0568 (14)	0.0339 (10)	−0.0015 (9)	0.0034 (8)	0.0003 (9)
C9	0.0231 (8)	0.0341 (10)	0.0377 (10)	−0.0006 (6)	0.0024 (7)	−0.0018 (7)
C10	0.0315 (9)	0.0352 (10)	0.0340 (10)	0.0008 (7)	0.0065 (7)	−0.0005 (7)

Geometric parameters (Å, º)

O1—C2	1.345 (2)	C42—H42B	0.99 (3)
O1—C9	1.405 (2)	C42—H42C	1.13 (5)
O2—C2	1.207 (3)	C5—C10	1.396 (3)
O6—C6	1.370 (2)	C5—C6	1.401 (3)
O6—H6	0.95 (3)	C5—C51	1.516 (3)
C2—C3	1.486 (3)	C51—H51A	1.00 (3)
C2—C3'	1.61 (9)	C51—H51B	0.93 (3)
C3—C3'	1.50 (9)	C51—H51C	0.97 (3)
C3—C4	1.537 (3)	C6—C7	1.401 (3)
C3—H3A	1.00 (3)	C7—C8	1.387 (2)
C3—H3B	0.94 (3)	C7—C71	1.511 (3)
C3'—C42	1.51 (9)	C71—H71A	0.99 (3)
C3'—C4	1.64 (9)	C71—H71B	0.97 (3)
C3'—H42C	1.35 (9)	C71—H71C	0.99 (3)
C4—C10	1.540 (3)	C8—C9	1.404 (2)
C4—C41	1.543 (4)	C8—C81	1.508 (3)
C4—C42	1.544 (4)	C81—H81A	0.97 (3)
C41—H41A	1.00 (3)	C81—H81B	1.00 (4)
C41—H41B	1.01 (5)	C81—H81C	0.98 (4)
C41—H41C	1.10 (4)	C9—C10	1.397 (3)
C42—H42A	0.99 (3)
C2—O1—C9	121.23 (16)	C3'—C42—H42A	89 (4)
C6—O6—H6	115 (2)	C4—C42—H42A	106.5 (17)
O2—C2—O1	117.1 (2)	C3'—C42—H42B	164 (4)
O2—C2—C3	127.3 (2)	C4—C42—H42B	104.4 (18)
O1—C2—C3	115.48 (18)	H42A—C42—H42B	106 (2)
O2—C2—C3'	111 (3)	C3'—C42—H42C	59 (4)
O1—C2—C3'	103 (3)	C4—C42—H42C	110 (2)
C3—C2—C3'	58 (3)	H42A—C42—H42C	112 (3)
C2—C3—C3'	65 (3)	H42B—C42—H42C	117 (3)
C2—C3—C4	113.48 (19)	C10—C5—C6	119.01 (17)
C3'—C3—C4	65 (3)	C10—C5—C51	124.59 (18)
C2—C3—H3A	105.7 (15)	C6—C5—C51	116.34 (18)
C3'—C3—H3A	85 (4)	C5—C51—H51A	108.1 (17)
C4—C3—H3A	110.9 (15)	C5—C51—H51B	109 (2)
C2—C3—H3B	106.1 (16)	H51A—C51—H51B	125 (3)
C3'—C3—H3B	164 (4)	C5—C51—H51C	107.5 (18)
C4—C3—H3B	109.8 (14)	H51A—C51—H51C	108 (2)
H3A—C3—H3B	111 (2)	H51B—C51—H51C	98 (3)
C3—C3'—C42	113 (6)	O6—C6—C5	115.76 (17)
C3—C3'—C2	57 (3)	O6—C6—C7	121.67 (16)
C42—C3'—C2	157 (6)	C5—C6—C7	122.56 (16)
C3—C3'—C4	58 (3)	C8—C7—C6	119.00 (16)
C42—C3'—C4	58 (3)	C8—C7—C71	121.63 (17)
C2—C3'—C4	102 (5)	C6—C7—C71	119.35 (16)
C3—C3'—H42C	151 (7)	C7—C71—H71A	109.0 (19)
C42—C3'—H42C	46 (4)	C7—C71—H71B	114.4 (14)
C2—C3'—H42C	133 (7)	H71A—C71—H71B	109 (2)
C4—C3'—H42C	94 (5)	C7—C71—H71C	113.8 (13)
C3—C4—C10	107.72 (17)	H71A—C71—H71C	109 (2)
C3—C4—C41	104.3 (2)	H71B—C71—H71C	101 (2)
C10—C4—C41	113.1 (2)	C7—C8—C9	117.82 (16)
C3—C4—C42	108.9 (2)	C7—C8—C81	122.60 (17)
C10—C4—C42	109.28 (19)	C9—C8—C81	119.57 (17)
C41—C4—C42	113.2 (3)	C8—C81—H81A	110.9 (17)
C3—C4—C3'	56 (3)	C8—C81—H81B	110.2 (19)
C10—C4—C3'	106 (3)	H81A—C81—H81B	106 (3)
C41—C4—C3'	141 (3)	C8—C81—H81C	114 (2)
C42—C4—C3'	56 (3)	H81A—C81—H81C	111 (2)
C4—C41—H41A	102.5 (16)	H81B—C81—H81C	104 (3)
C4—C41—H41B	113 (3)	C10—C9—C8	123.96 (16)
H41A—C41—H41B	110 (3)	C10—C9—O1	122.58 (16)
C4—C41—H41C	105.3 (18)	C8—C9—O1	113.25 (15)
H41A—C41—H41C	103 (2)	C5—C10—C9	117.51 (16)
H41B—C41—H41C	121 (3)	C5—C10—C4	125.55 (17)
C3'—C42—C4	65 (3)	C9—C10—C4	116.92 (16)
C9—O1—C2—O2	−175.12 (17)	C2—C3'—C42—C4	36 (15)
C9—O1—C2—C3	7.4 (3)	C3—C4—C42—C3'	21 (4)
C9—O1—C2—C3'	−53 (3)	C10—C4—C42—C3'	−96 (4)
O2—C2—C3—C3'	93 (4)	C41—C4—C42—C3'	137 (4)
O1—C2—C3—C3'	−90 (4)	C10—C5—C6—O6	178.89 (14)
O2—C2—C3—C4	138.3 (2)	C51—C5—C6—O6	−3.8 (2)
O1—C2—C3—C4	−44.6 (3)	C10—C5—C6—C7	−1.9 (2)
C3'—C2—C3—C4	45 (4)	C51—C5—C6—C7	175.43 (17)
C2—C3—C3'—C42	156 (6)	O6—C6—C7—C8	178.16 (14)
C4—C3—C3'—C42	22 (4)	C5—C6—C7—C8	−1.0 (2)
C4—C3—C3'—C2	−134 (3)	O6—C6—C7—C71	0.0 (2)
C2—C3—C3'—C4	134 (3)	C5—C6—C7—C71	−179.22 (16)
O2—C2—C3'—C3	−121.8 (17)	C6—C7—C8—C9	1.4 (2)
O1—C2—C3'—C3	112.1 (18)	C71—C7—C8—C9	179.58 (15)
O2—C2—C3'—C42	169 (15)	C6—C7—C8—C81	−178.49 (16)
O1—C2—C3'—C42	43 (16)	C71—C7—C8—C81	−0.3 (2)
C3—C2—C3'—C42	−70 (15)	C7—C8—C9—C10	1.1 (2)
O2—C2—C3'—C4	−160 (3)	C81—C8—C9—C10	−179.02 (16)
O1—C2—C3'—C4	74 (4)	C7—C8—C9—O1	−173.80 (13)
C3—C2—C3'—C4	−39 (3)	C81—C8—C9—O1	6.1 (2)
C2—C3—C4—C10	52.3 (3)	C2—O1—C9—C10	20.2 (2)
C3'—C3—C4—C10	97 (4)	C2—O1—C9—C8	−164.83 (16)
C2—C3—C4—C41	172.7 (3)	C6—C5—C10—C9	4.2 (2)
C3'—C3—C4—C41	−142 (4)	C51—C5—C10—C9	−172.90 (18)
C2—C3—C4—C42	−66.1 (3)	C6—C5—C10—C4	−177.37 (16)
C3'—C3—C4—C42	−21 (4)	C51—C5—C10—C4	5.6 (3)
C2—C3—C4—C3'	−45 (4)	C8—C9—C10—C5	−3.9 (2)
C42—C3'—C4—C3	−156 (4)	O1—C9—C10—C5	170.49 (14)
C2—C3'—C4—C3	38 (3)	C8—C9—C10—C4	177.50 (16)
C3—C3'—C4—C10	−101 (2)	O1—C9—C10—C4	−8.1 (2)
C42—C3'—C4—C10	103 (2)	C3—C4—C10—C5	154.83 (19)
C2—C3'—C4—C10	−63 (4)	C41—C4—C10—C5	40.1 (3)
C3—C3'—C4—C41	70 (5)	C42—C4—C10—C5	−87.0 (3)
C42—C3'—C4—C41	−86 (4)	C3'—C4—C10—C5	−146 (3)
C2—C3'—C4—C41	108 (4)	C3—C4—C10—C9	−26.7 (2)
C3—C3'—C4—C42	156 (4)	C41—C4—C10—C9	−141.4 (2)
C2—C3'—C4—C42	−166 (6)	C42—C4—C10—C9	91.5 (2)
C3—C3'—C42—C4	−22 (4)	C3'—C4—C10—C9	32 (3)

(cum250) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1268.5 (5) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.729 (1) Å	Dx = 1.227 Mg m^−3
b = 6.868 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.047 (4) Å	µ = 0.09 mm^−1
α = 90°	T = 250 K
β = 94.67 (2)°	, colourlees
γ = 90°	0.30 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 29.5°, θmin = 3.2°
8379 measured reflections	h = −13→12
3238 independent reflections	k = −4→9
1232 reflections with I > 2σ(I)	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.0604P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.014
3238 reflections	Δρmax = 0.21 e Å^−3
230 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (13)

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)
O1	0.10337 (16)	0.2341 (2)	0.24764 (9)	0.0475 (5)
O2	−0.11512 (19)	0.2351 (3)	0.26179 (13)	0.0789 (8)
O6	0.65065 (18)	0.2614 (2)	0.33858 (11)	0.0497 (5)
H6	0.716 (5)	0.257 (5)	0.307 (2)	0.121 (16)*
C2	−0.0005 (3)	0.2708 (4)	0.28712 (16)	0.0503 (8)
C3	0.0382 (3)	0.3624 (6)	0.35585 (18)	0.0581 (12)	0.965 (6)
H3A	−0.044 (3)	0.361 (4)	0.3830 (14)	0.067 (9)*
H3B	0.072 (3)	0.508 (4)	0.3479 (15)	0.069 (9)*
C3'	0.034 (9)	0.181 (15)	0.356 (5)	0.060*	0.035 (6)
C4	0.1637 (3)	0.2690 (4)	0.39565 (14)	0.0514 (8)
C41	0.1958 (6)	0.4032 (11)	0.4601 (3)	0.110 (2)
H41A	0.107 (4)	0.410 (5)	0.4806 (18)	0.097 (11)*
H41B	0.205 (9)	0.516 (13)	0.437 (5)	0.35 (6)*
H41C	0.267 (5)	0.349 (7)	0.491 (2)	0.141 (18)*
C42	0.1282 (5)	0.0578 (8)	0.4160 (3)	0.1006 (18)
H42A	0.210 (4)	0.032 (6)	0.452 (2)	0.143 (19)*
H42B	0.104 (7)	−0.026 (9)	0.369 (3)	0.23 (3)*
H42C	0.060 (3)	0.069 (4)	0.4481 (17)	0.091 (12)*
C5	0.4202 (2)	0.2586 (3)	0.36638 (12)	0.0369 (6)
C51	0.4813 (4)	0.2404 (6)	0.44203 (17)	0.0610 (9)
H51A	0.418 (3)	0.152 (5)	0.4703 (17)	0.093 (12)*
H51B	0.488 (3)	0.369 (5)	0.4617 (17)	0.098 (12)*
H51C	0.562 (4)	0.163 (4)	0.4424 (16)	0.092 (12)*
C6	0.5145 (2)	0.2622 (3)	0.31473 (13)	0.0331 (6)
C7	0.4730 (2)	0.2649 (3)	0.24281 (12)	0.0332 (6)
C71	0.5802 (3)	0.2670 (5)	0.19073 (18)	0.0456 (7)
H71A	0.538 (4)	0.289 (5)	0.145 (2)	0.107 (14)*
H71B	0.636 (3)	0.152 (4)	0.1953 (14)	0.071 (9)*
H71C	0.642 (3)	0.375 (4)	0.1945 (15)	0.083 (10)*
C8	0.3331 (2)	0.2609 (3)	0.22197 (12)	0.0320 (6)
C81	0.2806 (3)	0.2580 (5)	0.14588 (15)	0.0474 (7)
H81A	0.306 (3)	0.137 (5)	0.1193 (18)	0.111 (13)*
H81B	0.312 (3)	0.353 (4)	0.1171 (16)	0.079 (11)*
H81C	0.186 (5)	0.262 (5)	0.144 (2)	0.139 (17)*
C9	0.2419 (2)	0.2581 (3)	0.27421 (12)	0.0345 (6)
C10	0.2794 (2)	0.2633 (3)	0.34583 (12)	0.0353 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0250 (9)	0.0686 (13)	0.0493 (11)	−0.0039 (9)	0.0048 (8)	−0.0062 (10)
O2	0.0281 (11)	0.1108 (19)	0.0981 (18)	−0.0059 (12)	0.0068 (11)	−0.0159 (14)
O6	0.0280 (10)	0.0562 (12)	0.0634 (13)	0.0004 (9)	−0.0047 (9)	−0.0030 (11)
C2	0.0297 (14)	0.0606 (19)	0.0613 (19)	0.0029 (15)	0.0081 (14)	0.0035 (17)
C3	0.036	0.083 (3)	0.057 (2)	0.0139 (18)	0.0166 (16)	−0.002 (2)
C4	0.0441 (16)	0.070 (2)	0.0422 (16)	0.0123 (15)	0.0164 (13)	0.0102 (16)
C41	0.077 (3)	0.199 (6)	0.054 (3)	0.058 (3)	0.010 (2)	−0.032 (3)
C42	0.075 (3)	0.120 (4)	0.114 (4)	0.011 (3)	0.049 (3)	0.065 (4)
C5	0.0388 (14)	0.0339 (14)	0.0374 (14)	0.0011 (12)	−0.0007 (12)	−0.0020 (13)
C51	0.0543 (19)	0.078 (3)	0.0486 (19)	0.016 (2)	−0.0067 (15)	−0.002 (2)
C6	0.0250 (12)	0.0279 (13)	0.0456 (15)	0.0015 (11)	−0.0010 (11)	−0.0046 (12)
C7	0.0323 (13)	0.0281 (13)	0.0404 (14)	0.0007 (11)	0.0095 (11)	−0.0011 (12)
C71	0.0323 (14)	0.0461 (19)	0.060 (2)	0.0022 (15)	0.0158 (14)	0.0045 (18)
C8	0.0311 (12)	0.0304 (13)	0.0345 (13)	−0.0007 (11)	0.0022 (10)	0.0000 (12)
C81	0.0455 (18)	0.060 (2)	0.0364 (16)	−0.0066 (18)	0.0031 (13)	−0.0011 (18)
C9	0.0254 (12)	0.0366 (14)	0.0412 (15)	0.0006 (12)	0.0012 (10)	0.0002 (13)
C10	0.0332 (13)	0.0367 (14)	0.0366 (14)	0.0016 (12)	0.0064 (11)	0.0022 (13)

Geometric parameters (Å, º)

O1—C2	1.332 (3)	C42—H42A	1.02 (4)
O1—C9	1.410 (3)	C42—H42B	1.07 (6)
O2—C2	1.204 (3)	C42—H42C	0.94 (3)
O6—C6	1.365 (3)	C5—C10	1.394 (3)
O6—H6	0.91 (4)	C5—C6	1.399 (3)
C2—C3	1.473 (4)	C5—C51	1.518 (4)
C2—C3'	1.46 (10)	C51—H51A	1.04 (3)
C3—C3'	1.25 (10)	C51—H51B	0.96 (3)
C3—C4	1.525 (4)	C51—H51C	0.95 (3)
C3—H3A	0.98 (3)	C6—C7	1.396 (3)
C3—H3B	1.06 (3)	C7—C8	1.387 (3)
C3'—C4	1.54 (10)	C7—C71	1.496 (3)
C3'—C42	1.64 (10)	C71—H71A	0.95 (4)
C3'—H3A	1.56 (10)	C71—H71B	0.96 (3)
C3'—H42B	1.59 (11)	C71—H71C	0.95 (3)
C4—C10	1.531 (3)	C8—C9	1.386 (3)
C4—C41	1.547 (5)	C8—C81	1.497 (4)
C4—C42	1.548 (5)	C81—H81A	1.01 (4)
C41—H41A	0.97 (4)	C81—H81B	0.92 (3)
C41—H41B	0.90 (9)	C81—H81C	0.92 (5)
C41—H41C	0.95 (5)	C9—C10	1.384 (3)
C2—O1—C9	121.5 (2)	H41B—C41—H41C	123 (6)
C6—O6—H6	120 (3)	C4—C42—C3'	58 (3)
O2—C2—O1	117.1 (3)	C4—C42—H42A	99 (2)
O2—C2—C3	127.2 (3)	C3'—C42—H42A	156 (4)
O1—C2—C3	115.6 (2)	C4—C42—H42B	110 (3)
O2—C2—C3'	114 (4)	C3'—C42—H42B	68 (4)
O1—C2—C3'	107 (4)	H42A—C42—H42B	125 (4)
C3—C2—C3'	50 (4)	C4—C42—H42C	106 (2)
C3'—C3—C2	64 (5)	C3'—C42—H42C	92 (4)
C3'—C3—C4	67 (4)	H42A—C42—H42C	98 (3)
C2—C3—C4	113.5 (3)	H42B—C42—H42C	118 (4)
C3'—C3—H3A	88 (4)	C10—C5—C6	119.2 (2)
C2—C3—H3A	107.8 (15)	C10—C5—C51	124.6 (2)
C4—C3—H3A	112.7 (16)	C6—C5—C51	116.1 (2)
C3'—C3—H3B	161 (4)	C5—C51—H51A	109.7 (17)
C2—C3—H3B	109.4 (16)	C5—C51—H51B	108 (2)
C4—C3—H3B	102.8 (15)	H51A—C51—H51B	111 (3)
H3A—C3—H3B	111 (2)	C5—C51—H51C	108.3 (19)
C3—C3'—C2	65 (5)	H51A—C51—H51C	101 (3)
C3—C3'—C4	65 (4)	H51B—C51—H51C	119 (3)
C2—C3'—C4	113 (6)	O6—C6—C7	121.4 (2)
C3—C3'—C42	120 (7)	O6—C6—C5	116.1 (2)
C2—C3'—C42	156 (7)	C7—C6—C5	122.4 (2)
C4—C3'—C42	58 (3)	C8—C7—C6	118.6 (2)
C3—C3'—H3A	39 (3)	C8—C7—C71	122.1 (2)
C2—C3'—H3A	83 (5)	C6—C7—C71	119.3 (2)
C4—C3'—H3A	86 (5)	C7—C71—H71A	110 (2)
C42—C3'—H3A	116 (6)	C7—C71—H71B	110.6 (16)
C3—C3'—H42B	152 (8)	H71A—C71—H71B	114 (3)
C2—C3'—H42B	126 (7)	C7—C71—H71C	115.3 (18)
C4—C3'—H42B	87 (6)	H71A—C71—H71C	100 (3)
C42—C3'—H42B	39 (3)	H71B—C71—H71C	106 (3)
H3A—C3'—H42B	151 (8)	C9—C8—C7	117.8 (2)
C3—C4—C10	107.6 (2)	C9—C8—C81	120.4 (2)
C3—C4—C3'	48 (4)	C7—C8—C81	121.8 (2)
C10—C4—C3'	108 (3)	C8—C81—H81A	114.7 (19)
C3—C4—C41	104.3 (3)	C8—C81—H81B	117.4 (19)
C10—C4—C41	113.3 (3)	H81A—C81—H81B	100 (3)
C3'—C4—C41	137 (4)	C8—C81—H81C	108 (3)
C3—C4—C42	109.4 (3)	H81A—C81—H81C	106 (3)
C10—C4—C42	108.8 (3)	H81B—C81—H81C	110 (3)
C3'—C4—C42	64 (4)	C10—C9—C8	125.0 (2)
C41—C4—C42	113.2 (4)	C10—C9—O1	121.7 (2)
C4—C41—H41A	103 (2)	C8—C9—O1	113.1 (2)
C4—C41—H41B	98 (6)	C9—C10—C5	116.8 (2)
H41A—C41—H41B	106 (6)	C9—C10—C4	117.6 (2)
C4—C41—H41C	110 (3)	C5—C10—C4	125.6 (2)
H41A—C41—H41C	114 (3)
C9—O1—C2—O2	−175.5 (2)	C10—C4—C42—C3'	−101 (4)
C9—O1—C2—C3	8.0 (4)	C41—C4—C42—C3'	132 (4)
C9—O1—C2—C3'	−46 (4)	C3—C3'—C42—C4	−22 (5)
O2—C2—C3—C3'	92 (5)	C2—C3'—C42—C4	74 (17)
O1—C2—C3—C3'	−92 (5)	C10—C5—C6—O6	178.7 (2)
O2—C2—C3—C4	138.9 (3)	C51—C5—C6—O6	−4.0 (3)
O1—C2—C3—C4	−45.0 (4)	C10—C5—C6—C7	−1.8 (3)
C3'—C2—C3—C4	47 (5)	C51—C5—C6—C7	175.5 (3)
C4—C3—C3'—C2	−133 (3)	O6—C6—C7—C8	178.5 (2)
C2—C3—C3'—C4	133 (3)	C5—C6—C7—C8	−1.0 (3)
C2—C3—C3'—C42	154 (8)	O6—C6—C7—C71	0.0 (3)
C4—C3—C3'—C42	21 (4)	C5—C6—C7—C71	−179.5 (2)
O2—C2—C3'—C3	−119 (3)	C6—C7—C8—C9	1.2 (3)
O1—C2—C3'—C3	109 (3)	C71—C7—C8—C9	179.6 (2)
O2—C2—C3'—C4	−165 (4)	C6—C7—C8—C81	−178.3 (3)
O1—C2—C3'—C4	63 (6)	C71—C7—C8—C81	0.1 (4)
C3—C2—C3'—C4	−46 (4)	C7—C8—C9—C10	1.5 (4)
O2—C2—C3'—C42	132 (16)	C81—C8—C9—C10	−179.0 (3)
O1—C2—C3'—C42	1 (19)	C7—C8—C9—O1	−173.9 (2)
C3—C2—C3'—C42	−108 (19)	C81—C8—C9—O1	5.6 (3)
C3'—C3—C4—C10	98 (5)	C2—O1—C9—C10	19.6 (3)
C2—C3—C4—C10	52.3 (4)	C2—O1—C9—C8	−164.8 (2)
C2—C3—C4—C3'	−46 (5)	C8—C9—C10—C5	−4.3 (4)
C3'—C3—C4—C41	−141 (5)	O1—C9—C10—C5	170.8 (2)
C2—C3—C4—C41	172.9 (4)	C8—C9—C10—C4	177.1 (2)
C3'—C3—C4—C42	−20 (5)	O1—C9—C10—C4	−7.8 (3)
C2—C3—C4—C42	−65.7 (4)	C6—C5—C10—C9	4.3 (3)
C2—C3'—C4—C3	46 (5)	C51—C5—C10—C9	−172.8 (3)
C42—C3'—C4—C3	−159 (5)	C6—C5—C10—C4	−177.3 (2)
C3—C3'—C4—C10	−98 (3)	C51—C5—C10—C4	5.7 (4)
C2—C3'—C4—C10	−52 (7)	C3—C4—C10—C9	−26.6 (3)
C42—C3'—C4—C10	102.8 (19)	C3'—C4—C10—C9	24 (4)
C3—C3'—C4—C41	62 (6)	C41—C4—C10—C9	−141.3 (4)
C2—C3'—C4—C41	108 (6)	C42—C4—C10—C9	91.8 (3)
C42—C3'—C4—C41	−97 (4)	C3—C4—C10—C5	154.9 (3)
C3—C3'—C4—C42	159 (5)	C3'—C4—C10—C5	−155 (4)
C2—C3'—C4—C42	−155 (7)	C41—C4—C10—C5	40.2 (4)
C3—C4—C42—C3'	16 (4)	C42—C4—C10—C5	−86.6 (4)

(cum278) 6-hydroxy-4,4,5,6,7-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1276.2 (6) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.739 (2) Å	Dx = 1.219 Mg m^−3
b = 6.895 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.066 (5) Å	µ = 0.09 mm^−1
α = 90°	T = 278 K
β = 94.57 (3)°	, colourlees
γ = 90°	0.30 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 29.4°, θmin = 3.6°
7992 measured reflections	h = −13→12
3226 independent reflections	k = −4→9
892 reflections with I > 2σ(I)	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0425P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.82	(Δ/σ)max = 1.707
3226 reflections	Δρmax = 0.15 e Å^−3
262 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (10)

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)
O1	0.10405 (15)	0.2359 (3)	0.24767 (9)	0.0579 (5)
O2	−0.11485 (19)	0.2371 (3)	0.26196 (12)	0.0948 (8)
O6	0.65040 (17)	0.2599 (3)	0.33850 (11)	0.0577 (6)
H6	0.711 (3)	0.249 (5)	0.3045 (18)	0.116 (14)*
C2	−0.0007 (3)	0.2677 (5)	0.28746 (16)	0.0613 (8)
C3	0.0400 (4)	0.3604 (7)	0.3562 (2)	0.0689 (13)	0.904 (3)
H3A	−0.0401	0.354 (4)	0.3809 (15)	0.070 (10)*	0.904 (3)
H3B	0.073 (3)	0.516 (4)	0.3477 (14)	0.070 (9)*	0.904 (3)
C3'	0.028 (3)	0.162 (5)	0.3580 (17)	0.041*	0.096 (3)
H3C	0.0578	0.0174	0.3454	0.09 (11)*	0.096 (3)
H3D	−0.0447	0.1490	0.3837	0.09 (11)*	0.096 (3)
C4	0.1643 (3)	0.2654 (5)	0.39573 (14)	0.0607 (8)
C41	0.1948 (5)	0.4001 (12)	0.4601 (3)	0.115 (2)	0.904 (3)
H41A	0.2163	0.5238	0.4447	0.19 (11)*	0.904 (3)
H41B	0.2713	0.3458	0.4889	0.144 (18)*	0.904 (3)
H41C	0.1157	0.4023	0.4872	0.130 (15)*	0.904 (3)
C41'	0.208 (7)	0.124 (6)	0.475 (3)	0.094*	0.096 (3)
H41D	0.1193	0.1182	0.4916	0.11 (9)*	0.096 (3)
H41E	0.2778	0.1458	0.4875	0.2 (3)*	0.096 (3)
H41F	0.2000	−0.0168	0.4435	0.04 (8)*	0.096 (3)
C42	0.1296 (6)	0.0606 (9)	0.4172 (4)	0.114 (2)	0.904 (3)
H42A	0.0573	0.0649	0.4490	0.092 (11)*	0.904 (3)
H42B	0.2094	0.0021	0.4408	0.14 (3)*	0.904 (3)
H42C	0.0996	−0.0124	0.3768	0.19 (3)*	0.904 (3)
C42'	0.122 (6)	0.476 (6)	0.415 (3)	0.089*	0.096 (3)
H42D	0.0608	0.4451	0.4486	0.13 (15)*	0.096 (3)
H42E	0.1057	0.5270	0.3775	2 (5)*	0.096 (3)
H42F	0.2138	0.5056	0.4419	0.8 (13)*	0.096 (3)
C5	0.4200 (2)	0.2569 (4)	0.36607 (12)	0.0426 (6)
C51	0.4805 (5)	0.2412 (9)	0.44131 (18)	0.0708 (10)
H51A	0.414 (5)	0.177 (8)	0.468 (3)	0.027 (16)*	0.50
H51B	0.534 (8)	0.377 (11)	0.454 (3)	0.08 (2)*	0.50
H51C	0.572 (6)	0.125 (9)	0.440 (2)	0.06 (2)*	0.50
H51D	0.581 (7)	0.233 (15)	0.442 (3)	0.08 (2)*	0.50
H51E	0.448 (13)	0.085 (13)	0.460 (5)	0.19 (5)*	0.50
H51F	0.461 (6)	0.372 (9)	0.472 (3)	0.07 (2)*	0.50
C6	0.5133 (2)	0.2595 (4)	0.31427 (13)	0.0395 (6)
C7	0.4732 (2)	0.2633 (3)	0.24280 (12)	0.0367 (6)
C71	0.5801 (3)	0.2647 (7)	0.1909 (2)	0.0528 (9)
H71A	0.712 (10)	0.246 (16)	0.215 (5)	0.20 (4)*	0.50
H71B	0.572 (8)	0.192 (10)	0.156 (4)	0.08 (3)*	0.50
H71C	0.520 (5)	0.272 (9)	0.140 (3)	0.040 (15)*	0.50
H71D	0.591 (9)	0.366 (11)	0.146 (4)	0.14 (3)*	0.50
H71E	0.637 (5)	0.150 (6)	0.194 (3)	0.013 (12)*	0.50
H71F	0.647 (4)	0.372 (5)	0.201 (2)	0.000 (10)*	0.50
C8	0.3330 (2)	0.2588 (4)	0.22223 (12)	0.0366 (6)
C81	0.2806 (4)	0.2590 (7)	0.14611 (16)	0.0525 (8)
H81A	0.368 (7)	0.343 (10)	0.103 (3)	0.11 (2)*	0.50
H81B	0.163 (4)	0.310 (5)	0.148 (2)	0.031 (12)*	0.50
H81C	0.308 (6)	0.103 (8)	0.124 (3)	0.06 (2)*	0.50
H81D	0.204 (5)	0.176 (6)	0.137 (2)	0.028 (15)*	0.50
H81E	0.277 (5)	0.377 (6)	0.128 (2)	0.032 (16)*	0.50
H81F	0.334 (4)	0.191 (7)	0.119 (2)	0.005 (13)*	0.50
C9	0.2421 (2)	0.2565 (4)	0.27452 (13)	0.0401 (6)
C10	0.2794 (2)	0.2616 (4)	0.34575 (12)	0.0403 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0274 (9)	0.0871 (14)	0.0594 (12)	−0.0058 (12)	0.0040 (9)	−0.0042 (13)
O2	0.0337 (12)	0.135 (2)	0.1159 (18)	−0.0065 (15)	0.0062 (12)	−0.0153 (16)
O6	0.0336 (10)	0.0684 (13)	0.0696 (14)	0.0014 (12)	−0.0057 (10)	−0.0038 (13)
C2	0.0356 (16)	0.074 (2)	0.075 (2)	0.003 (2)	0.0113 (16)	0.006 (2)
C3	0.041 (2)	0.102 (4)	0.066 (3)	0.012 (2)	0.022 (2)	−0.004 (3)
C4	0.0504 (18)	0.083 (2)	0.0507 (18)	0.014 (2)	0.0187 (15)	0.017 (2)
C41	0.090 (4)	0.203 (8)	0.053 (3)	0.061 (4)	0.010 (3)	−0.030 (3)
C42	0.083 (3)	0.137 (4)	0.131 (5)	0.019 (3)	0.059 (4)	0.082 (5)
C5	0.0396 (14)	0.0463 (16)	0.0411 (15)	0.0000 (18)	−0.0012 (13)	−0.0005 (19)
C51	0.058 (2)	0.095 (3)	0.057 (2)	0.006 (3)	−0.007 (2)	−0.006 (3)
C6	0.0288 (13)	0.0373 (15)	0.0516 (17)	−0.0006 (17)	−0.0029 (12)	−0.0062 (18)
C7	0.0370 (14)	0.0306 (13)	0.0434 (16)	0.0006 (16)	0.0092 (12)	−0.0031 (16)
C71	0.0401 (18)	0.055 (2)	0.065 (2)	0.001 (2)	0.0158 (17)	−0.006 (3)
C8	0.0370 (14)	0.0317 (14)	0.0407 (15)	−0.0009 (16)	0.0018 (12)	−0.0004 (17)
C81	0.051 (2)	0.063 (3)	0.045 (2)	−0.001 (3)	0.0068 (16)	−0.009 (3)
C9	0.0257 (13)	0.0448 (15)	0.0500 (17)	−0.0018 (16)	0.0037 (11)	−0.0027 (19)
C10	0.0376 (14)	0.0446 (15)	0.0392 (16)	−0.0002 (17)	0.0070 (12)	0.0023 (18)

Geometric parameters (Å, º)

O1—C2	1.337 (3)	C42—H41F	0.975 (6)
O1—C9	1.407 (2)	C42—H42A	0.966 (5)
O2—C2	1.196 (3)	C42—H42B	0.955 (6)
O6—C6	1.378 (3)	C42—H42C	0.947 (9)
O6—H6	0.92 (4)	C42'—H3B	1.37 (5)
C2—C3	1.484 (5)	C42'—H41A	1.09 (6)
C2—C3'	1.54 (3)	C42'—H41C	1.47 (5)
C3—C3'	1.38 (3)	C42'—H42D	0.93 (5)
C3—C4	1.522 (4)	C42'—H42E	0.81 (6)
C3—C42'	1.55 (5)	C42'—H42F	1.01 (6)
C3—H3A	0.944 (15)	C5—C10	1.393 (3)
C3—H3B	1.14 (3)	C5—C6	1.395 (3)
C3—H42E	1.361 (5)	C5—C51	1.511 (4)
C3'—C42	1.60 (3)	C51—H51A	0.96 (6)
C3'—C4	1.62 (3)	C51—H51B	1.09 (7)
C3'—H3C	1.07 (3)	C51—H51C	1.20 (5)
C3'—H3D	0.90 (3)	C51—H51D	0.97 (6)
C3'—H42C	1.42 (3)	C51—H51E	1.18 (10)
C4—C42	1.516 (5)	C51—H51F	1.10 (6)
C4—C10	1.528 (3)	C6—C7	1.387 (3)
C4—C42'	1.56 (4)	C7—C8	1.391 (3)
C4—C41	1.549 (5)	C7—C71	1.493 (3)
C4—C41'	1.82 (5)	C71—H71A	1.34 (10)
C41—C42'	1.19 (6)	C71—H71B	0.83 (6)
C41—C41'	1.93 (4)	C71—H71C	1.09 (5)
C41—H41A	0.932 (9)	C71—H71D	1.11 (8)
C41—H41B	0.966 (5)	C71—H71E	0.96 (4)
C41—H41C	0.960 (5)	C71—H71F	1.00 (4)
C41—H42D	1.343 (5)	C8—C9	1.385 (3)
C41—H42F	0.834 (9)	C8—C81	1.499 (4)
C41'—C42	1.36 (6)	C81—H81A	1.36 (6)
C41'—H41D	0.94 (6)	C81—H81B	1.20 (4)
C41'—H41E	0.72 (7)	C81—H81C	1.19 (6)
C41'—H41F	1.14 (5)	C81—H81D	0.95 (4)
C41'—H42B	1.06 (5)	C81—H81E	0.89 (4)
C42—H3C	1.517 (9)	C81—H81F	0.90 (5)
C42—H41D	1.484 (8)	C9—C10	1.378 (3)
C2—O1—C9	121.8 (2)	C3'—C42—H42A	89.4 (12)
C6—O6—H6	115 (2)	H3C—C42—H42A	105.4 (6)
O2—C2—O1	117.8 (3)	H41D—C42—H42A	44.2 (4)
O2—C2—C3	127.5 (3)	H41F—C42—H42A	102.3 (5)
O1—C2—C3	114.2 (3)	C41'—C42—H42B	51.2 (19)
O2—C2—C3'	111.8 (12)	C4—C42—H42B	109.3 (6)
O1—C2—C3'	108.9 (12)	C3'—C42—H42B	161.7 (12)
C3—C2—C3'	54.1 (11)	H3C—C42—H42B	129.9 (7)
C3'—C3—C2	64.9 (14)	H41D—C42—H42B	77.1 (5)
C3'—C3—C4	67.9 (13)	H41F—C42—H42B	9.99 (6)
C2—C3—C4	113.4 (3)	H42A—C42—H42B	108.9 (6)
C3'—C3—C42'	122 (2)	C41'—C42—H42C	161 (2)
C2—C3—C42'	161.8 (18)	C4—C42—H42C	109.6 (5)
C4—C3—C42'	61.1 (17)	C3'—C42—H42C	61.6 (12)
C3'—C3—H3A	82 (2)	H3C—C42—H42C	21.69 (19)
C2—C3—H3A	104.4 (16)	H41D—C42—H42C	151.7 (4)
C4—C3—H3A	112.9 (16)	H41F—C42—H42C	106.6 (6)
C42'—C3—H3A	93 (2)	H42A—C42—H42C	109.5 (7)
C3'—C3—H3B	166 (2)	H42B—C42—H42C	110.2 (6)
C2—C3—H3B	109.8 (14)	C41—C42'—C4	67 (2)
C4—C3—H3B	104.8 (13)	C41—C42'—C3	123 (3)
C42'—C3—H3B	58.9 (18)	C4—C42'—C3	58.6 (16)
H3A—C3—H3B	112 (2)	C41—C42'—H3B	156 (4)
C3'—C3—H42E	150.7 (14)	C4—C42'—H3B	93 (3)
C2—C3—H42E	135.5 (3)	C3—C42'—H3B	45 (2)
C4—C3—H42E	83.0 (3)	C41—C42'—H41A	48 (2)
C42'—C3—H42E	31.3 (18)	C4—C42'—H41A	100 (3)
H3A—C3—H42E	106.1 (17)	C3—C42'—H41A	154 (4)
H3B—C3—H42E	27.6 (13)	H3B—C42'—H41A	130 (4)
C3—C3'—C2	60.9 (14)	C41—C42'—H41C	40.7 (18)
C3—C3'—C42	114 (2)	C4—C42'—H41C	86 (2)
C2—C3'—C42	152 (2)	C3—C42'—H41C	116 (3)
C3—C3'—C4	60.3 (12)	H3B—C42'—H41C	156 (5)
C2—C3'—C4	105.3 (18)	H41A—C42'—H41C	74 (3)
C42—C3'—C4	56.1 (11)	C41—C42'—H42D	78 (4)
C3—C3'—H3C	154 (3)	C4—C42'—H42D	98 (3)
C2—C3'—H3C	106 (2)	C3—C42'—H42D	93 (4)
C42—C3'—H3C	65.8 (17)	H3B—C42'—H42D	120 (5)
C4—C3'—H3C	106 (2)	H41A—C42'—H42D	106 (5)
C3—C3'—H3D	101 (3)	H41C—C42'—H42D	37 (2)
C2—C3'—H3D	115 (3)	C41—C42'—H42E	154 (6)
C42—C3'—H3D	93 (2)	C4—C42'—H42E	103 (4)
C4—C3'—H3D	117 (3)	C3—C42'—H42E	61 (3)
H3C—C3'—H3D	106 (3)	H3B—C42'—H42E	16.2 (19)
C3—C3'—H42C	144 (2)	H41A—C42'—H42E	115 (5)
C2—C3'—H42C	132 (2)	H41C—C42'—H42E	165 (5)
C42—C3'—H42C	35.9 (8)	H42D—C42'—H42E	128 (7)
C4—C3'—H42C	83.9 (16)	C41—C42'—H42F	44 (2)
H3C—C3'—H42C	30.0 (9)	C4—C42'—H42F	94 (3)
H3D—C3'—H42C	100 (3)	C3—C42'—H42F	149 (4)
C42—C4—C3	110.4 (4)	H3B—C42'—H42F	131 (5)
C42—C4—C10	110.1 (3)	H41A—C42'—H42F	6.3 (4)
C3—C4—C10	107.0 (2)	H41C—C42'—H42F	73 (3)
C42—C4—C42'	137.1 (18)	H42D—C42'—H42F	107 (5)
C3—C4—C42'	60 (2)	H42E—C42'—H42F	118 (5)
C10—C4—C42'	112.6 (18)	C10—C5—C6	119.0 (2)
C42—C4—C41	112.1 (5)	C10—C5—C51	124.5 (3)
C3—C4—C41	103.2 (3)	C6—C5—C51	116.5 (3)
C10—C4—C41	113.6 (3)	C5—C51—H51A	108 (3)
C42'—C4—C41	45 (2)	C5—C51—H51B	107 (3)
C42—C4—C3'	61.2 (12)	H51A—C51—H51B	128 (5)
C3—C4—C3'	51.7 (11)	C5—C51—H51C	105 (2)
C10—C4—C3'	109.3 (11)	H51A—C51—H51C	104 (4)
C42'—C4—C3'	107 (2)	H51B—C51—H51C	104 (5)
C41—C4—C3'	135.5 (12)	C5—C51—H51D	110 (3)
C42—C4—C41'	47.0 (18)	H51A—C51—H51D	132 (5)
C3—C4—C41'	139.9 (19)	H51B—C51—H51D	65 (4)
C10—C4—C41'	112.0 (17)	H51C—C51—H51D	39 (5)
C42'—C4—C41'	110 (2)	C5—C51—H51E	105 (4)
C41—C4—C41'	69.3 (16)	H51A—C51—H51E	38 (6)
C3'—C4—C41'	105 (2)	H51B—C51—H51E	148 (5)
C42'—C41—C4	68 (2)	H51C—C51—H51E	68 (5)
C42'—C41—C41'	125 (3)	H51D—C51—H51E	104 (7)
C4—C41—C41'	61.9 (16)	C5—C51—H51F	112 (3)
C42'—C41—H41A	60 (2)	H51A—C51—H51F	86 (4)
C4—C41—H41A	109.4 (5)	H51B—C51—H51F	44 (4)
C41'—C41—H41A	159.5 (16)	H51C—C51—H51F	136 (4)
C42'—C41—H41B	166 (2)	H51D—C51—H51F	105 (6)
C4—C41—H41B	108.0 (5)	H51E—C51—H51F	121 (6)
C41'—C41—H41B	60 (2)	O6—C6—C7	121.2 (2)
H41A—C41—H41B	110.6 (7)	O6—C6—C5	115.6 (2)
C42'—C41—H41C	86 (2)	C7—C6—C5	123.2 (2)
C4—C41—H41C	108.9 (6)	C6—C7—C8	118.0 (2)
C41'—C41—H41C	89.1 (16)	C6—C7—C71	119.7 (3)
H41A—C41—H41C	111.4 (6)	C8—C7—C71	122.3 (2)
H41B—C41—H41C	108.4 (6)	C7—C71—H71A	118 (4)
C42'—C41—H42D	43 (2)	C7—C71—H71B	120 (5)
C4—C41—H42D	83.5 (3)	H71A—C71—H71B	104 (7)
C41'—C41—H42D	108 (2)	C7—C71—H71C	104 (3)
H41A—C41—H42D	88.7 (5)	H71A—C71—H71C	138 (5)
H41B—C41—H42D	151.6 (7)	H71B—C71—H71C	46 (6)
H41C—C41—H42D	43.44 (19)	C7—C71—H71D	129 (4)
C42'—C41—H42F	57 (2)	H71A—C71—H71D	100 (6)
C4—C41—H42F	103.1 (4)	H71B—C71—H71D	77 (6)
C41'—C41—H42F	155.3 (15)	H71C—C71—H71D	51 (4)
H41A—C41—H42F	6.32 (7)	C7—C71—H71E	112 (2)
H41B—C41—H42F	112.8 (7)	H71A—C71—H71E	51 (4)
H41C—C41—H42F	115.2 (6)	H71B—C71—H71E	65 (5)
H42D—C41—H42F	88.6 (5)	H71C—C71—H71E	111 (4)
C42—C41'—C4	54.8 (18)	H71D—C71—H71E	119 (5)
C42—C41'—C41	100 (3)	C7—C71—H71F	111 (2)
C4—C41'—C41	48.8 (10)	H71A—C71—H71F	54 (4)
C42—C41'—H41D	78 (5)	H71B—C71—H71F	128 (5)
C4—C41'—H41D	98 (4)	H71C—C71—H71F	116 (4)
C41—C41'—H41D	92 (3)	H71D—C71—H71F	65 (4)
C42—C41'—H41E	142 (5)	H71E—C71—H71F	104 (3)
C4—C41'—H41E	109 (4)	C9—C8—C7	117.8 (2)
C41—C41'—H41E	84 (4)	C9—C8—C81	120.6 (2)
H41D—C41'—H41E	139 (6)	C7—C8—C81	121.6 (2)
C42—C41'—H41F	45 (2)	C8—C81—H81A	114 (3)
C4—C41'—H41F	91 (3)	C8—C81—H81B	103.2 (19)
C41—C41'—H41F	140 (4)	H81A—C81—H81B	122 (3)
H41D—C41'—H41F	97 (5)	C8—C81—H81C	106 (2)
H41E—C41'—H41F	112 (5)	H81A—C81—H81C	90 (4)
C42—C41'—H42B	44 (2)	H81B—C81—H81C	121 (3)
C4—C41'—H42B	86 (3)	C8—C81—H81D	112 (3)
C41—C41'—H42B	134 (3)	H81A—C81—H81D	132 (4)
H41D—C41'—H42B	103 (6)	H81B—C81—H81D	56 (3)
H41E—C41'—H42B	108 (5)	H81C—C81—H81D	65 (3)
H41F—C41'—H42B	7.9 (4)	C8—C81—H81E	113 (3)
C41'—C42—C4	78.2 (18)	H81A—C81—H81E	51 (3)
C41'—C42—C3'	135 (2)	H81B—C81—H81E	74 (3)
C4—C42—C3'	62.7 (11)	H81C—C81—H81E	134 (4)
C41'—C42—H3C	169 (2)	H81D—C81—H81E	118 (4)
C4—C42—H3C	92.0 (3)	C8—C81—H81F	113 (3)
C3'—C42—H3C	40.0 (12)	H81A—C81—H81F	57 (3)
C41'—C42—H41D	38 (2)	H81B—C81—H81F	140 (3)
C4—C42—H41D	92.4 (5)	H81C—C81—H81F	34 (4)
C3'—C42—H41D	118.2 (12)	H81D—C81—H81F	94 (4)
H3C—C42—H41D	148.7 (4)	H81E—C81—H81F	105 (5)
C41'—C42—H41F	55.6 (18)	C10—C9—C8	125.2 (2)
C4—C42—H41F	119.0 (6)	C10—C9—O1	122.0 (2)
C3'—C42—H41F	166.0 (14)	C8—C9—O1	112.7 (2)
H3C—C42—H41F	127.7 (7)	C9—C10—C5	116.7 (2)
H41D—C42—H41F	75.8 (5)	C9—C10—C4	117.8 (2)
C41'—C42—H42A	83 (2)	C5—C10—C4	125.5 (2)
C4—C42—H42A	109.3 (5)
C9—O1—C2—O2	−176.1 (3)	C42'—C41—C41'—C42	7 (5)
C9—O1—C2—C3	10.9 (4)	C4—C41—C41'—C42	−20.9 (16)
C9—O1—C2—C3'	−47.4 (13)	C42'—C41—C41'—C4	28 (3)
O2—C2—C3—C3'	91.2 (15)	C41—C41'—C42—C4	19.2 (16)
O1—C2—C3—C3'	−96.5 (15)	C4—C41'—C42—C3'	−30 (3)
O2—C2—C3—C4	140.3 (4)	C41—C41'—C42—C3'	−11 (4)
O1—C2—C3—C4	−47.5 (4)	C3—C4—C42—C41'	−140 (2)
C3'—C2—C3—C4	49.1 (14)	C10—C4—C42—C41'	102 (2)
O2—C2—C3—C42'	−151 (6)	C42'—C4—C42—C41'	−72 (4)
O1—C2—C3—C42'	21 (6)	C41—C4—C42—C41'	−26 (2)
C3'—C2—C3—C42'	118 (6)	C3'—C4—C42—C41'	−157 (3)
C4—C3—C3'—C2	−131.6 (10)	C3—C4—C42—C3'	16.4 (14)
C42'—C3—C3'—C2	−161 (2)	C10—C4—C42—C3'	−101.6 (13)
C2—C3—C3'—C42	149 (2)	C42'—C4—C42—C3'	84 (3)
C4—C3—C3'—C42	17.8 (14)	C41—C4—C42—C3'	130.9 (13)
C42'—C3—C3'—C42	−12 (3)	C41'—C4—C42—C3'	157 (3)
C2—C3—C3'—C4	131.6 (10)	C3—C3'—C42—C41'	15 (4)
C42'—C3—C3'—C4	−29 (2)	C2—C3'—C42—C41'	87 (6)
O2—C2—C3'—C3	−121.4 (9)	C4—C3'—C42—C41'	33 (4)
O1—C2—C3'—C3	106.7 (10)	C3—C3'—C42—C4	−18.6 (15)
O2—C2—C3'—C42	152 (4)	C2—C3'—C42—C4	54 (4)
O1—C2—C3'—C42	20 (5)	C41'—C41—C42'—C4	−27 (3)
C3—C2—C3'—C42	−86 (5)	C4—C41—C42'—C3	19 (3)
O2—C2—C3'—C4	−163.7 (11)	C41'—C41—C42'—C3	−8 (6)
O1—C2—C3'—C4	64.3 (18)	C42—C4—C42'—C41	73 (3)
C3—C2—C3'—C4	−42.4 (10)	C3—C4—C42'—C41	161 (3)
C3'—C3—C4—C42	−18.3 (15)	C10—C4—C42'—C41	−101.4 (19)
C2—C3—C4—C42	−65.9 (5)	C3'—C4—C42'—C41	138.5 (19)
C42'—C3—C4—C42	133 (2)	C41'—C4—C42'—C41	25 (3)
C3'—C3—C4—C10	101.4 (15)	C42—C4—C42'—C3	−89 (3)
C2—C3—C4—C10	53.9 (4)	C10—C4—C42'—C3	97.3 (13)
C42'—C3—C4—C10	−107 (2)	C41—C4—C42'—C3	−161 (3)
C3'—C3—C4—C42'	−152 (2)	C3'—C4—C42'—C3	−22.8 (19)
C2—C3—C4—C42'	161 (2)	C41'—C4—C42'—C3	−137 (2)
C3'—C3—C4—C41	−138.4 (15)	C3'—C3—C42'—C41	11 (5)
C2—C3—C4—C41	174.0 (4)	C2—C3—C42'—C41	−98 (6)
C42'—C3—C4—C41	13 (2)	C4—C3—C42'—C41	−21 (3)
C2—C3—C4—C3'	−47.6 (14)	C3'—C3—C42'—C4	31 (3)
C42'—C3—C4—C3'	152 (2)	C2—C3—C42'—C4	−77 (6)
C3'—C3—C4—C41'	−65 (3)	C10—C5—C6—O6	178.3 (2)
C2—C3—C4—C41'	−112 (3)	C51—C5—C6—O6	−4.0 (4)
C42'—C3—C4—C41'	87 (3)	C10—C5—C6—C7	−1.1 (4)
C3—C3'—C4—C42	160.3 (16)	C51—C5—C6—C7	176.6 (3)
C2—C3'—C4—C42	−157 (2)	O6—C6—C7—C8	178.8 (2)
C2—C3'—C4—C3	42.7 (11)	C5—C6—C7—C8	−1.8 (4)
C42—C3'—C4—C3	−160.3 (16)	O6—C6—C7—C71	1.0 (4)
C3—C3'—C4—C10	−96.8 (10)	C5—C6—C7—C71	−179.7 (3)
C2—C3'—C4—C10	−54.1 (19)	C6—C7—C8—C9	1.8 (4)
C42—C3'—C4—C10	102.8 (8)	C71—C7—C8—C9	179.6 (3)
C3—C3'—C4—C42'	25 (2)	C6—C7—C8—C81	−178.9 (3)
C2—C3'—C4—C42'	68 (3)	C71—C7—C8—C81	−1.2 (5)
C42—C3'—C4—C42'	−135 (2)	C7—C8—C9—C10	1.2 (4)
C3—C3'—C4—C41	67.3 (19)	C81—C8—C9—C10	−178.1 (3)
C2—C3'—C4—C41	109.9 (17)	C7—C8—C9—O1	−175.1 (2)
C42—C3'—C4—C41	−93.1 (15)	C81—C8—C9—O1	5.7 (4)
C3—C3'—C4—C41'	142.9 (17)	C2—O1—C9—C10	16.8 (4)
C2—C3'—C4—C41'	−174.5 (19)	C2—O1—C9—C8	−166.8 (3)
C42—C3'—C4—C41'	−17.5 (18)	C8—C9—C10—C5	−4.1 (4)
C42—C4—C41—C42'	−135 (3)	O1—C9—C10—C5	171.8 (2)
C3—C4—C41—C42'	−17 (3)	C8—C9—C10—C4	177.8 (3)
C10—C4—C41—C42'	99 (3)	O1—C9—C10—C4	−6.2 (4)
C3'—C4—C41—C42'	−65 (3)	C6—C5—C10—C9	3.9 (4)
C41'—C4—C41—C42'	−155 (3)	C51—C5—C10—C9	−173.6 (4)
C42—C4—C41—C41'	20 (2)	C6—C5—C10—C4	−178.2 (3)
C3—C4—C41—C41'	139 (2)	C51—C5—C10—C4	4.3 (5)
C10—C4—C41—C41'	−106 (2)	C42—C4—C10—C9	92.5 (4)
C42'—C4—C41—C41'	155 (3)	C3—C4—C10—C9	−27.6 (4)
C3'—C4—C41—C41'	91 (3)	C42'—C4—C10—C9	−92 (2)
C3—C4—C41'—C42	68 (2)	C41—C4—C10—C9	−140.8 (4)
C10—C4—C41'—C42	−97.4 (19)	C3'—C4—C10—C9	27.0 (13)
C42'—C4—C41'—C42	136 (2)	C41'—C4—C10—C9	143 (2)
C41—C4—C41'—C42	155 (2)	C42—C4—C10—C5	−85.4 (5)
C3'—C4—C41'—C42	21 (2)	C3—C4—C10—C5	154.6 (3)
C42—C4—C41'—C41	−155 (2)	C42'—C4—C10—C5	90 (2)
C3—C4—C41'—C41	−86 (3)	C41—C4—C10—C5	41.3 (5)
C10—C4—C41'—C41	108.0 (7)	C3'—C4—C10—C5	−150.8 (13)
C42'—C4—C41'—C41	−18 (3)	C41'—C4—C10—C5	−35 (2)
C3'—C4—C41'—C41	−133.5 (13)

(cum285) 6-hydrohy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1291.7 (10) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.768 (6) Å	Dx = 1.205 Mg m^−3
b = 6.933 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.130 (4) Å	µ = 0.08 mm^−1
α = 90°	T = 285 K
β = 94.39 (4)°	, colourlees
γ = 90°	0.44 × 0.38 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 29.6°, θmin = 3.7°
7944 measured reflections	h = −6→13
3313 independent reflections	k = −9→9
1715 reflections with I > 2σ(I)	l = −26→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.225	w = 1/[σ^2(Fo^2) + (0.1297P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 1.085
3313 reflections	Δρmax = 0.35 e Å^−3
275 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.002 (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)
O1	0.10328 (12)	0.23771 (18)	0.24761 (7)	0.0593 (4)
O2	−0.11509 (14)	0.2375 (2)	0.26193 (12)	0.0963 (7)
O6	0.65005 (13)	0.25892 (16)	0.33843 (9)	0.0588 (4)
H6	0.715 (3)	0.247 (3)	0.3034 (17)	0.105 (10)*
C2	−0.00100 (19)	0.2660 (3)	0.28728 (13)	0.0647 (6)
C3	0.0379 (2)	0.3603 (4)	0.35627 (14)	0.0689 (10)	0.853 (6)
H3A	−0.0401	0.3560	0.3849	0.106 (10)*	0.853 (6)
H3B	0.0581	0.4968	0.3485	0.080 (8)*	0.853 (6)
C3'	0.0387 (13)	0.158 (3)	0.3562 (7)	0.078 (7)	0.147 (6)
H3C	0.0578	0.0174	0.3454	0.19 (13)*	0.147 (6)
H3D	−0.0447	0.1489	0.3837	0.18 (10)*	0.147 (6)
C4	0.1636 (2)	0.2644 (3)	0.39574 (11)	0.0632 (6)
C41	0.1960 (4)	0.3968 (8)	0.46015 (19)	0.1131 (17)	0.853 (6)
H41A	0.2163	0.5238	0.4447	0.23 (4)*	0.853 (6)
H41B	0.2713	0.3458	0.4889	0.20 (2)*	0.853 (6)
H41C	0.1157	0.4023	0.4872	0.126 (11)*	0.853 (6)
C41'	0.199 (2)	0.113 (5)	0.4626 (10)	0.113 (10)	0.147 (6)
H41D	0.1193	0.1182	0.4916	0.012 (19)*	0.147 (6)
H41E	0.2778	0.1458	0.4875	0.12 (7)*	0.147 (6)
H41F	0.2000	−0.0168	0.4435	1.0 (11)*	0.147 (6)
C42	0.1273 (4)	0.0584 (7)	0.4159 (3)	0.1091 (17)	0.853 (6)
H42A	0.0573	0.0649	0.4491	0.143 (13)*	0.853 (6)
H42B	0.2094	0.0021	0.4408	0.129 (18)*	0.853 (6)
H42C	0.0996	−0.0124	0.3768	0.18 (3)*	0.853 (6)
C42'	0.1252 (17)	0.471 (3)	0.4094 (11)	0.095 (8)	0.147 (6)
H42D	0.0608	0.4451	0.4486	0.06 (4)*	0.147 (6)
H42E	0.1057	0.5270	0.3775	2 (3)*	0.147 (6)
H42F	0.2138	0.5056	0.4419	0.05 (6)*	0.147 (6)
C5	0.42048 (17)	0.2570 (2)	0.36645 (9)	0.0431 (4)
C51	0.4814 (3)	0.2428 (4)	0.44148 (12)	0.0711 (7)
H51A	0.423 (6)	0.177 (10)	0.475 (3)	0.074 (18)*	0.50
H51B	0.542 (5)	0.378 (7)	0.453 (2)	0.066 (12)*	0.50
H51C	0.574 (4)	0.133 (6)	0.4421 (17)	0.048 (10)*	0.50
H51D	0.577 (7)	0.256 (9)	0.445 (3)	0.079 (16)*	0.50
H51E	0.433 (7)	0.116 (10)	0.460 (4)	0.10 (3)*	0.50
H51F	0.451 (5)	0.376 (7)	0.467 (2)	0.075 (12)*	0.50
C6	0.51400 (16)	0.2593 (2)	0.31461 (10)	0.0430 (4)
C7	0.47287 (16)	0.26209 (19)	0.24283 (9)	0.0401 (4)
C71	0.5799 (2)	0.2638 (3)	0.19008 (12)	0.0527 (5)
H71A	0.666 (5)	0.353 (6)	0.211 (2)	0.052 (12)*	0.50
H71B	0.539 (3)	0.312 (5)	0.1414 (18)	0.035 (8)*	0.50
H71C	0.636 (3)	0.146 (4)	0.1935 (14)	0.015 (6)*	0.50
H71D	0.556 (4)	0.182 (7)	0.152 (2)	0.061 (12)*	0.50
H71E	0.694 (9)	0.206 (11)	0.209 (4)	0.14 (3)*	0.50
H71F	0.626 (4)	0.387 (6)	0.185 (2)	0.047 (11)*	0.50
C8	0.33363 (17)	0.2584 (2)	0.22200 (9)	0.0402 (4)
C81	0.2801 (2)	0.2564 (3)	0.14591 (10)	0.0554 (5)
H81A	0.394 (10)	0.301 (12)	0.115 (4)	0.18 (3)*	0.50
H81B	0.198 (4)	0.369 (6)	0.137 (2)	0.062 (11)*	0.50
H81C	0.211 (5)	0.139 (7)	0.135 (2)	0.083 (15)*	0.50
H81D	0.183 (4)	0.248 (6)	0.142 (2)	0.038 (10)*	0.50
H81E	0.310 (3)	0.369 (4)	0.1223 (15)	0.025 (7)*	0.50
H81F	0.322 (3)	0.142 (4)	0.1225 (15)	0.031 (7)*	0.50
C9	0.24061 (15)	0.2568 (2)	0.27413 (9)	0.0404 (4)
C10	0.27948 (17)	0.2605 (2)	0.34580 (9)	0.0432 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0297 (7)	0.0912 (11)	0.0572 (8)	−0.0028 (5)	0.0038 (6)	−0.0045 (6)
O2	0.0324 (8)	0.1445 (19)	0.1126 (16)	−0.0033 (7)	0.0080 (8)	−0.0141 (10)
O6	0.0328 (7)	0.0701 (9)	0.0720 (9)	0.0010 (5)	−0.0063 (6)	−0.0037 (6)
C2	0.0309 (9)	0.0837 (15)	0.0806 (15)	0.0025 (8)	0.0117 (9)	0.0036 (11)
C3	0.0450 (12)	0.093 (3)	0.0706 (16)	0.0158 (13)	0.0189 (11)	0.0000 (14)
C3'	0.044 (7)	0.14 (2)	0.051 (8)	−0.030 (9)	0.013 (6)	0.027 (10)
C4	0.0504 (11)	0.0904 (16)	0.0512 (11)	0.0091 (9)	0.0184 (9)	0.0034 (9)
C41	0.084 (2)	0.197 (5)	0.0594 (18)	0.051 (3)	0.0124 (19)	−0.034 (3)
C41'	0.087 (14)	0.21 (3)	0.046 (9)	−0.046 (15)	0.009 (10)	0.052 (15)
C42	0.081 (2)	0.131 (3)	0.121 (4)	0.012 (2)	0.047 (3)	0.063 (3)
C42'	0.053 (9)	0.144 (17)	0.091 (14)	−0.012 (10)	0.031 (10)	−0.051 (13)
C5	0.0415 (9)	0.0431 (9)	0.0441 (9)	0.0028 (6)	−0.0001 (7)	−0.0033 (6)
C51	0.0623 (14)	0.101 (2)	0.0485 (12)	0.0060 (13)	−0.0073 (10)	−0.0012 (12)
C6	0.0303 (8)	0.0404 (9)	0.0578 (10)	0.0020 (6)	0.0006 (7)	0.0002 (7)
C7	0.0334 (8)	0.0381 (8)	0.0496 (9)	0.0005 (5)	0.0083 (6)	0.0002 (6)
C71	0.0419 (10)	0.0527 (12)	0.0657 (13)	0.0001 (8)	0.0187 (9)	0.0003 (10)
C8	0.0358 (8)	0.0422 (9)	0.0430 (9)	0.0005 (6)	0.0053 (6)	−0.0008 (6)
C81	0.0495 (11)	0.0737 (15)	0.0428 (10)	−0.0023 (10)	0.0022 (8)	0.0003 (9)
C9	0.0284 (7)	0.0464 (9)	0.0466 (9)	−0.0002 (6)	0.0035 (6)	−0.0017 (7)
C10	0.0399 (9)	0.0466 (9)	0.0440 (9)	0.0003 (6)	0.0085 (7)	−0.0005 (7)

Geometric parameters (Å, º)

O1—C2	1.331 (2)	C42—H41F	0.999 (4)
O1—C9	1.403 (2)	C42—H42A	0.969 (3)
O2—C2	1.197 (3)	C42—H42B	0.982 (4)
O6—C6	1.371 (2)	C42—H42C	0.917 (7)
O6—H6	0.96 (3)	C42'—H3B	1.30 (2)
C2—C3	1.496 (4)	C42'—H41A	1.138 (19)
C2—C3'	1.538 (15)	C42'—H41C	1.57 (2)
C3—C3'	1.40 (2)	C42'—H42D	1.031 (16)
C3—C42'	1.487 (19)	C42'—H42E	0.74 (3)
C3—C4	1.542 (3)	C42'—H42F	1.05 (2)
C3—H3A	0.972 (2)	C5—C6	1.399 (2)
C3—H3B	0.980 (3)	C5—C10	1.404 (2)
C3—H42E	1.377 (3)	C5—C51	1.514 (3)
C3'—C42	1.543 (16)	C51—H51A	0.99 (6)
C3'—C4	1.568 (15)	C51—H51B	1.12 (5)
C3'—H3C	1.02 (2)	C51—H51C	1.18 (4)
C3'—H3D	1.005 (12)	C51—H51D	0.94 (6)
C3'—H42C	1.37 (2)	C51—H51E	1.08 (7)
C4—C42'	1.51 (2)	C51—H51F	1.10 (5)
C4—C42	1.528 (4)	C6—C7	1.401 (3)
C4—C10	1.537 (2)	C7—C8	1.388 (2)
C4—C41	1.549 (4)	C7—C71	1.508 (2)
C4—C41'	1.67 (2)	C71—H71A	1.10 (4)
C41—C42'	1.26 (3)	C71—H71B	1.04 (4)
C41—C41'	1.97 (4)	C71—H71C	0.98 (3)
C41—H41A	0.954 (6)	C71—H71D	0.94 (5)
C41—H41B	0.953 (4)	C71—H71E	1.22 (9)
C41—H41C	0.972 (3)	C71—H71F	0.98 (4)
C41—H42D	1.364 (4)	C8—C9	1.400 (2)
C41—H42F	0.855 (6)	C8—C81	1.509 (3)
C41'—C42	1.15 (2)	C81—H81A	1.34 (9)
C41'—H41D	0.987 (19)	C81—H81B	1.12 (4)
C41'—H41E	0.91 (2)	C81—H81C	1.07 (5)
C41'—H41F	0.97 (4)	C81—H81D	0.95 (4)
C41'—H42A	1.42 (2)	C81—H81E	0.96 (3)
C41'—H42B	0.89 (4)	C81—H81F	1.01 (3)
C42—H3C	1.490 (7)	C9—C10	1.395 (2)
C42—H41D	1.515 (6)
C2—O1—C9	122.16 (16)	H3C—C42—H41F	129.4 (5)
C6—O6—H6	116 (2)	H41D—C42—H41F	74.0 (4)
O2—C2—O1	118.3 (2)	C41'—C42—H42A	83.7 (11)
O2—C2—C3	126.5 (2)	C4—C42—H42A	108.1 (4)
O1—C2—C3	114.44 (17)	C3'—C42—H42A	94.6 (6)
O2—C2—C3'	115.7 (5)	H3C—C42—H42A	107.9 (4)
O1—C2—C3'	105.3 (6)	H41D—C42—H42A	43.1 (3)
C3—C2—C3'	54.9 (8)	H41F—C42—H42A	100.8 (4)
C3'—C3—C42'	120.8 (12)	C41'—C42—H42B	48.2 (17)
C3'—C3—C2	64.1 (6)	C4—C42—H42B	107.3 (4)
C42'—C3—C2	157.1 (6)	C3'—C42—H42B	158.2 (5)
C3'—C3—C4	64.2 (6)	H3C—C42—H42B	131.5 (5)
C42'—C3—C4	59.6 (9)	H41D—C42—H42B	75.2 (4)
C2—C3—C4	112.49 (19)	H41F—C42—H42B	9.78 (4)
C3'—C3—H3A	88.5 (5)	H42A—C42—H42B	106.9 (5)
C42'—C3—H3A	93.7 (5)	C41'—C42—H42C	158.3 (16)
C2—C3—H3A	109.0 (2)	C4—C42—H42C	110.8 (3)
C4—C3—H3A	109.9 (2)	C3'—C42—H42C	61.6 (9)
C3'—C3—H3B	164.6 (5)	H3C—C42—H42C	22.39 (15)
C42'—C3—H3B	59.7 (10)	H41D—C42—H42C	153.1 (3)
C2—C3—H3B	109.3 (2)	H41F—C42—H42C	107.7 (4)
C4—C3—H3B	109.1 (2)	H42A—C42—H42C	112.4 (5)
H3A—C3—H3B	106.9 (2)	H42B—C42—H42C	111.2 (4)
C3'—C3—H42E	146.8 (6)	C41—C42'—C3	124.9 (18)
C42'—C3—H42E	29.5 (10)	C41—C42'—C4	67.6 (12)
C2—C3—H42E	135.3 (2)	C3—C42'—C4	62.0 (7)
C4—C3—H42E	82.56 (16)	C41—C42'—H3B	162.9 (17)
H3A—C3—H42E	103.9 (2)	C3—C42'—H3B	40.5 (6)
H3B—C3—H42E	30.30 (9)	C4—C42'—H3B	95.3 (11)
C3—C3'—C2	61.0 (7)	C41—C42'—H41A	46.6 (9)
C3—C3'—C42	116.8 (12)	C3—C42'—H41A	162.7 (15)
C2—C3'—C42	160.4 (9)	C4—C42'—H41A	102.6 (16)
C3—C3'—C4	62.3 (8)	H3B—C42'—H41A	143.4 (19)
C2—C3'—C4	108.8 (10)	C41—C42'—H41C	38.2 (7)
C42—C3'—C4	58.8 (6)	C3—C42'—H41C	114.8 (12)
C3—C3'—H3C	163.8 (11)	C4—C42'—H41C	84.9 (13)
C2—C3'—H3C	109.2 (12)	H3B—C42'—H41C	145.6 (11)
C42—C3'—H3C	67.6 (10)	H41A—C42'—H41C	68.6 (12)
C4—C3'—H3C	113.5 (12)	C41—C42'—H42D	72.4 (15)
C3—C3'—H3D	93.5 (16)	C3—C42'—H42D	93.4 (11)
C2—C3'—H3D	108.6 (13)	C4—C42'—H42D	97.9 (17)
C42—C3'—H3D	90.8 (9)	H3B—C42'—H42D	112.3 (15)
C4—C3'—H3D	114.2 (14)	H41A—C42'—H42D	96.7 (17)
H3C—C3'—H3D	102.2 (14)	H41C—C42'—H42D	34.5 (8)
C3—C3'—H42C	150.1 (11)	C41—C42'—H42E	161.3 (18)
C2—C3'—H42C	137.8 (14)	C3—C42'—H42E	67.0 (14)
C42—C3'—H42C	36.1 (5)	C4—C42'—H42E	114.3 (17)
C4—C3'—H42C	87.8 (8)	H3B—C42'—H42E	26.7 (8)
H3C—C3'—H42C	31.5 (6)	H41A—C42'—H42E	117 (2)
H3D—C3'—H42C	98.3 (12)	H41C—C42'—H42E	156.0 (17)
C42'—C4—C42	141.1 (7)	H42D—C42'—H42E	124 (2)
C42'—C4—C10	109.3 (6)	C41—C42'—H42F	42.3 (9)
C42—C4—C10	109.64 (19)	C3—C42'—H42F	157.4 (16)
C42'—C4—C3	58.4 (8)	C4—C42'—H42F	96.7 (16)
C42—C4—C3	109.6 (3)	H3B—C42'—H42F	145.9 (19)
C10—C4—C3	107.47 (16)	H41A—C42'—H42F	5.85 (12)
C42'—C4—C41	48.6 (9)	H41C—C42'—H42F	67.4 (13)
C42—C4—C41	113.0 (3)	H42D—C42'—H42F	97.5 (18)
C10—C4—C41	112.9 (2)	H42E—C42'—H42F	121 (2)
C3—C4—C41	103.9 (2)	C6—C5—C10	118.70 (16)
C42'—C4—C3'	109.5 (11)	C6—C5—C51	116.26 (17)
C42—C4—C3'	59.8 (7)	C10—C5—C51	125.00 (17)
C10—C4—C3'	105.9 (5)	C5—C51—H51A	116 (3)
C3—C4—C3'	53.5 (8)	C5—C51—H51B	107 (2)
C41—C4—C3'	139.9 (6)	H51A—C51—H51B	125 (4)
C42'—C4—C41'	120.2 (14)	C5—C51—H51C	107.2 (16)
C42—C4—C41'	42.1 (10)	H51A—C51—H51C	100 (4)
C10—C4—C41'	110.4 (8)	H51B—C51—H51C	98 (3)
C3—C4—C41'	139.0 (7)	C5—C51—H51D	112 (3)
C41—C4—C41'	75.2 (12)	H51A—C51—H51D	128 (5)
C3'—C4—C41'	100.5 (11)	H51B—C51—H51D	53 (3)
C42'—C41—C4	63.9 (8)	H51C—C51—H51D	46 (3)
C42'—C41—C41'	115.5 (12)	C5—C51—H51E	103 (4)
C4—C41—C41'	55.1 (6)	H51A—C51—H51E	29 (5)
C42'—C41—H41A	60.1 (9)	H51B—C51—H51E	149 (4)
C4—C41—H41A	109.6 (3)	H51C—C51—H51E	80 (4)
C41'—C41—H41A	158.0 (5)	H51D—C51—H51E	121 (5)
C42'—C41—H41B	162.2 (7)	C5—C51—H51F	106 (2)
C4—C41—H41B	110.0 (4)	H51A—C51—H51F	85 (4)
C41'—C41—H41B	66.9 (8)	H51B—C51—H51F	51 (2)
H41A—C41—H41B	110.5 (5)	H51C—C51—H51F	140 (3)
C42'—C41—H41C	88.7 (7)	H51D—C51—H51F	101 (4)
C4—C41—H41C	108.8 (4)	H51E—C51—H51F	113 (5)
C41'—C41—H41C	92.1 (7)	O6—C6—C5	115.66 (17)
H41A—C41—H41C	108.9 (4)	O6—C6—C7	121.57 (16)
H41B—C41—H41C	109.0 (4)	C5—C6—C7	122.76 (15)
C42'—C41—H42D	46.1 (6)	C8—C7—C6	118.84 (15)
C4—C41—H42D	83.1 (2)	C8—C7—C71	121.51 (17)
C41'—C41—H42D	105.0 (7)	C6—C7—C71	119.64 (15)
H41A—C41—H42D	86.9 (3)	C7—C71—H71A	108 (2)
H41B—C41—H42D	151.7 (4)	C7—C71—H71B	111.3 (17)
H41C—C41—H42D	42.84 (14)	H71A—C71—H71B	112 (3)
C42'—C41—H42F	56.1 (9)	C7—C71—H71C	111.2 (15)
C4—C41—H42F	103.5 (3)	H71A—C71—H71C	92 (3)
C41'—C41—H42F	152.8 (6)	H71B—C71—H71C	120 (2)
H41A—C41—H42F	6.15 (5)	C7—C71—H71D	112 (2)
H41B—C41—H42F	113.0 (5)	H71A—C71—H71D	140 (3)
H41C—C41—H42F	112.4 (4)	H71B—C71—H71D	56 (3)
H42D—C41—H42F	86.7 (3)	H71C—C71—H71D	70 (3)
C42—C41'—C4	62.5 (9)	C7—C71—H71E	118 (4)
C42—C41'—C41	107.8 (17)	H71A—C71—H71E	54 (4)
C4—C41'—C41	49.6 (8)	H71B—C71—H71E	131 (4)
C42—C41'—H41D	89.7 (17)	H71C—C71—H71E	38 (4)
C4—C41'—H41D	107 (2)	H71D—C71—H71E	102 (5)
C41—C41'—H41D	88 (2)	C7—C71—H71F	115 (2)
C42—C41'—H41E	158 (3)	H71A—C71—H71F	36 (3)
C4—C41'—H41E	111.3 (19)	H71B—C71—H71F	78 (3)
C41—C41'—H41E	77 (2)	H71C—C71—H71F	118 (3)
H41D—C41'—H41E	112 (2)	H71D—C71—H71F	123 (3)
C42—C41'—H41F	55.2 (15)	H71E—C71—H71F	84 (4)
C4—C41'—H41F	107.6 (16)	C7—C8—C9	118.10 (15)
C41—C41'—H41F	156.6 (14)	C7—C8—C81	122.49 (16)
H41D—C41'—H41F	106 (2)	C9—C8—C81	119.41 (16)
H41E—C41'—H41F	113 (3)	C8—C81—H81A	101 (4)
C42—C41'—H42A	42.6 (8)	C8—C81—H81B	109.2 (19)
C4—C41'—H42A	82.5 (11)	H81A—C81—H81B	112 (4)
C41—C41'—H42A	102.8 (17)	C8—C81—H81C	111 (2)
H41D—C41'—H42A	47.2 (9)	H81A—C81—H81C	129 (4)
H41E—C41'—H42A	158.6 (19)	H81B—C81—H81C	94 (4)
H41F—C41'—H42A	75.9 (16)	C8—C81—H81D	111 (2)
C42—C41'—H42B	55.7 (16)	H81A—C81—H81D	147 (5)
C4—C41'—H42B	102.2 (15)	H81B—C81—H81D	48 (2)
C41—C41'—H42B	149.3 (13)	H81C—C81—H81D	48 (3)
H41D—C41'—H42B	115 (3)	C8—C81—H81E	110.4 (17)
H41E—C41'—H42B	110 (3)	H81A—C81—H81E	46 (4)
H41F—C41'—H42B	9.0 (4)	H81B—C81—H81E	67 (2)
H42A—C41'—H42B	81.9 (19)	H81C—C81—H81E	138 (3)
C41'—C42—C4	75.5 (14)	H81D—C81—H81E	111 (3)
C41'—C42—C3'	134.1 (18)	C8—C81—H81F	108.1 (16)
C4—C42—C3'	61.4 (7)	H81A—C81—H81F	67 (4)
C41'—C42—H3C	165.8 (8)	H81B—C81—H81F	142 (3)
C4—C42—H3C	92.8 (2)	H81C—C81—H81F	66 (3)
C3'—C42—H3C	39.2 (8)	H81D—C81—H81F	111 (3)
C41'—C42—H41D	40.7 (10)	H81E—C81—H81F	106 (3)
C4—C42—H41D	90.9 (3)	C10—C9—C8	123.89 (15)
C3'—C42—H41D	121.2 (8)	C10—C9—O1	122.53 (15)
H3C—C42—H41D	149.9 (2)	C8—C9—O1	113.45 (15)
C41'—C42—H41F	53.1 (17)	C9—C10—C5	117.63 (16)
C4—C42—H41F	116.8 (4)	C9—C10—C4	116.96 (16)
C3'—C42—H41F	164.0 (8)	C5—C10—C4	125.40 (17)
C9—O1—C2—O2	−176.27 (16)	C42'—C41—C41'—C42	−2.5 (16)
C9—O1—C2—C3	12.8 (3)	C4—C41—C41'—C42	−24.5 (8)
C9—O1—C2—C3'	−45.2 (8)	C42'—C41—C41'—C4	22.1 (9)
O2—C2—C3—C3'	98.0 (6)	C41—C41'—C42—C4	20.9 (6)
O1—C2—C3—C3'	−92.0 (6)	C4—C41'—C42—C3'	−20.2 (14)
O2—C2—C3—C42'	−154 (3)	C41—C41'—C42—C3'	1 (2)
O1—C2—C3—C42'	16 (3)	C42'—C4—C42—C41'	−79.7 (19)
C3'—C2—C3—C42'	108 (3)	C10—C4—C42—C41'	99.0 (14)
O2—C2—C3—C4	141.5 (2)	C3—C4—C42—C41'	−143.3 (13)
O1—C2—C3—C4	−48.4 (3)	C41—C4—C42—C41'	−28.0 (14)
C3'—C2—C3—C4	43.6 (6)	C3'—C4—C42—C41'	−163.6 (15)
C42'—C3—C3'—C2	−154.5 (7)	C42'—C4—C42—C3'	83.9 (16)
C4—C3—C3'—C2	−135.0 (5)	C10—C4—C42—C3'	−97.4 (7)
C42'—C3—C3'—C42	3.4 (12)	C3—C4—C42—C3'	20.3 (7)
C2—C3—C3'—C42	157.9 (10)	C41—C4—C42—C3'	135.6 (7)
C4—C3—C3'—C42	22.9 (6)	C41'—C4—C42—C3'	163.6 (15)
C42'—C3—C3'—C4	−19.5 (8)	C3—C3'—C42—C41'	−1.4 (19)
C2—C3—C3'—C4	135.0 (5)	C2—C3'—C42—C41'	77 (5)
O2—C2—C3'—C3	−118.0 (4)	C4—C3'—C42—C41'	22.4 (16)
O1—C2—C3'—C3	109.4 (4)	C3—C3'—C42—C4	−23.8 (6)
O2—C2—C3'—C42	153 (4)	C2—C3'—C42—C4	55 (5)
O1—C2—C3'—C42	20 (5)	C4—C41—C42'—C3	25.0 (8)
C3—C2—C3'—C42	−89 (5)	C41'—C41—C42'—C3	4.9 (14)
O2—C2—C3'—C4	−159.4 (6)	C41'—C41—C42'—C4	−20.1 (8)
O1—C2—C3'—C4	68.0 (12)	C3'—C3—C42'—C41	−5.8 (15)
C3—C2—C3'—C4	−41.4 (8)	C2—C3—C42'—C41	−102 (3)
C3'—C3—C4—C42'	−160.6 (10)	C4—C3—C42'—C41	−26.3 (8)
C2—C3—C4—C42'	156.0 (8)	C3'—C3—C42'—C4	20.4 (9)
C3'—C3—C4—C42	−21.9 (6)	C2—C3—C42'—C4	−75 (3)
C42'—C3—C4—C42	138.7 (8)	C42—C4—C42'—C41	74.7 (12)
C2—C3—C4—C42	−65.4 (3)	C10—C4—C42'—C41	−104.0 (7)
C3'—C3—C4—C10	97.2 (6)	C3—C4—C42'—C41	156.9 (9)
C42'—C3—C4—C10	−102.3 (8)	C3'—C4—C42'—C41	140.4 (6)
C2—C3—C4—C10	53.7 (2)	C41'—C4—C42'—C41	25.0 (11)
C3'—C3—C4—C41	−142.9 (6)	C42—C4—C42'—C3	−82.2 (14)
C42'—C3—C4—C41	17.7 (8)	C10—C4—C42'—C3	99.1 (4)
C2—C3—C4—C41	173.6 (3)	C41—C4—C42'—C3	−156.9 (9)
C42'—C3—C4—C3'	160.6 (10)	C3'—C4—C42'—C3	−16.5 (8)
C2—C3—C4—C3'	−43.5 (6)	C41'—C4—C42'—C3	−131.9 (9)
C3'—C3—C4—C41'	−59.5 (19)	C10—C5—C6—O6	178.96 (12)
C42'—C3—C4—C41'	101.1 (19)	C51—C5—C6—O6	−3.4 (2)
C2—C3—C4—C41'	−103.0 (18)	C10—C5—C6—C7	−1.0 (2)
C3—C3'—C4—C42'	17.5 (10)	C51—C5—C6—C7	176.68 (16)
C2—C3'—C4—C42'	58.3 (13)	O6—C6—C7—C8	178.70 (13)
C42—C3'—C4—C42'	−138.5 (9)	C5—C6—C7—C8	−1.3 (2)
C3—C3'—C4—C42	156.0 (7)	O6—C6—C7—C71	0.3 (2)
C2—C3'—C4—C42	−163.2 (14)	C5—C6—C7—C71	−179.77 (15)
C3—C3'—C4—C10	−100.2 (5)	C6—C7—C8—C9	1.51 (19)
C2—C3'—C4—C10	−59.4 (12)	C71—C7—C8—C9	179.92 (14)
C42—C3'—C4—C10	103.8 (4)	C6—C7—C8—C81	−178.56 (15)
C2—C3'—C4—C3	40.8 (8)	C71—C7—C8—C81	−0.2 (2)
C42—C3'—C4—C3	−156.0 (7)	C7—C8—C9—C10	0.6 (2)
C3—C3'—C4—C41	65.5 (9)	C81—C8—C9—C10	−179.30 (15)
C2—C3'—C4—C41	106.3 (8)	C7—C8—C9—O1	−175.26 (12)
C42—C3'—C4—C41	−90.6 (11)	C81—C8—C9—O1	4.8 (2)
C3—C3'—C4—C41'	144.9 (11)	C2—O1—C9—C10	15.8 (2)
C2—C3'—C4—C41'	−174.3 (14)	C2—O1—C9—C8	−168.30 (15)
C42—C3'—C4—C41'	−11.1 (12)	C8—C9—C10—C5	−2.9 (2)
C42—C4—C41—C42'	−138.9 (8)	O1—C9—C10—C5	172.59 (13)
C10—C4—C41—C42'	96.0 (8)	C8—C9—C10—C4	178.12 (14)
C3—C4—C41—C42'	−20.2 (8)	O1—C9—C10—C4	−6.4 (2)
C3'—C4—C41—C42'	−69.0 (13)	C6—C5—C10—C9	3.01 (19)
C41'—C4—C41—C42'	−157.8 (11)	C51—C5—C10—C9	−174.45 (17)
C42'—C4—C41—C41'	157.8 (11)	C6—C5—C10—C4	−178.13 (14)
C42—C4—C41—C41'	18.9 (7)	C51—C5—C10—C4	4.4 (3)
C10—C4—C41—C41'	−106.2 (7)	C42'—C4—C10—C9	−89.0 (9)
C3—C4—C41—C41'	137.6 (7)	C42—C4—C10—C9	91.9 (3)
C3'—C4—C41—C41'	88.8 (13)	C3—C4—C10—C9	−27.2 (2)
C42'—C4—C41'—C42	134.4 (12)	C41—C4—C10—C9	−141.2 (3)
C10—C4—C41'—C42	−97.1 (9)	C3'—C4—C10—C9	28.8 (8)
C3—C4—C41'—C42	59 (2)	C41'—C4—C10—C9	136.7 (12)
C41—C4—C41'—C42	153.5 (12)	C42'—C4—C10—C5	92.1 (9)
C3'—C4—C41'—C42	14.4 (14)	C42—C4—C10—C5	−87.0 (3)
C42'—C4—C41'—C41	−19.1 (9)	C3—C4—C10—C5	153.96 (18)
C42—C4—C41'—C41	−153.5 (12)	C41—C4—C10—C5	39.9 (3)
C10—C4—C41'—C41	109.4 (5)	C3'—C4—C10—C5	−150.0 (8)
C3—C4—C41'—C41	−94.4 (13)	C41'—C4—C10—C5	−42.1 (12)
C3'—C4—C41'—C41	−139.1 (7)

(cum293) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Crystal data

C14H18O3	V = 1285.0 (4) Å^3
Mr = 234.28	Z = 4
P21/c, monoclinic	F(000) = 504
a = 9.744 (2) Å	Dx = 1.211 Mg m^−3
b = 6.922 (1) Å	Mo Kα radiation, λ = 0.71073 Å
c = 19.109 (4) Å	µ = 0.08 mm^−1
α = 90°	T = 293 K
β = 94.44 (3)°	, colourlees
γ = 90°	0.35 × 0.25 × 0.12 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.1°, θmin = 2.1°
10609 measured reflections	h = −11→11
2273 independent reflections	k = −8→6
2059 reflections with I > 2σ(I)	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.120	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.327	w = 1/[σ^2(Fo^2) + (0.1331P)^2 + 0.7198P] where P = (Fo^2 + 2Fc^2)/3
S = 1.36	(Δ/σ)max = 0.202
2273 reflections	Δρmax = 0.41 e Å^−3
254 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (8)

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)
O1	0.1032 (3)	0.2393 (4)	0.24762 (15)	0.0613 (9)
O2	−0.1144 (3)	0.2401 (5)	0.2618 (2)	0.0976 (15)
O6	0.6496 (3)	0.2573 (4)	0.3385 (2)	0.0609 (9)
H6	0.700 (6)	0.250 (6)	0.311 (3)	0.078 (19)*
C2	−0.0008 (4)	0.2641 (6)	0.2870 (3)	0.0647 (13)
C3	0.0389 (5)	0.3558 (10)	0.3563 (3)	0.0734 (19)	0.80
H3A	−0.0390	0.3495	0.3850	0.058 (14)*	0.80
H3B	0.0581	0.4937	0.3493	0.074 (18)*	0.80
C3'	0.041 (3)	0.139 (3)	0.3580 (13)	0.082 (8)	0.20
H31A	0.03 (3)	0.08 (4)	0.315 (16)	0.122*	0.20
H31B	−0.05 (3)	0.21 (4)	0.400 (17)	0.122*	0.20
C4	0.1634 (5)	0.2618 (6)	0.3955 (2)	0.0642 (13)
C41	0.1986 (18)	0.394 (3)	0.4597 (9)	0.161 (9)	0.80
H41A	0.102 (9)	0.385 (14)	0.485 (4)	0.17 (3)*
H41B	0.181 (5)	0.434 (6)	0.456 (3)	0.013 (10)*
H41C	0.224 (10)	0.263 (11)	0.491 (5)	0.15 (3)*
C41'	0.181 (3)	0.116 (5)	0.4599 (17)	0.080 (7)*	0.20
C42	0.1276 (8)	0.0539 (14)	0.4162 (5)	0.100 (3)	0.80
H42A	0.057 (11)	0.076 (15)	0.459 (6)	0.18 (4)*	0.80
H42B	0.219 (4)	0.023 (6)	0.4525 (19)	0.020 (9)*	0.80
H42C	0.091 (6)	−0.029 (8)	0.370 (3)	0.072 (18)*	0.80
C42'	0.118 (3)	0.468 (5)	0.4062 (17)	0.093 (8)*	0.20
H42D	0.11 (3)	0.59 (5)	0.479 (16)	0.139*	0.20
H42E	0.10 (3)	0.62 (5)	0.378 (17)	0.139*	0.20
H42F	0.22 (4)	0.55 (5)	0.425 (19)	0.139*	0.20
C5	0.4201 (4)	0.2560 (4)	0.36604 (19)	0.0432 (9)
C51	0.4805 (5)	0.2450 (7)	0.4413 (2)	0.0737 (15)
H51A	0.4075	0.2450	0.4723	0.111*
H51B	0.5391	0.3546	0.4514	0.111*
H51C	0.5333	0.1284	0.4480	0.111*
C6	0.5137 (3)	0.2573 (4)	0.3144 (2)	0.0418 (9)
C7	0.4727 (3)	0.2604 (4)	0.24260 (19)	0.0390 (9)
C71	0.5803 (4)	0.2606 (6)	0.1905 (3)	0.0517 (11)
H71A	0.536 (7)	0.269 (7)	0.145 (4)	0.11 (2)*
H71B	0.641 (4)	0.146 (6)	0.195 (2)	0.067 (12)*
H71C	0.640 (5)	0.374 (8)	0.192 (3)	0.098 (16)*
C8	0.3332 (4)	0.2568 (4)	0.22213 (19)	0.0399 (9)
C81	0.2804 (5)	0.2560 (7)	0.1466 (2)	0.0551 (11)
H81A	0.337 (7)	0.307 (10)	0.111 (4)	0.028 (16)*	0.50
H81B	0.192 (7)	0.303 (9)	0.135 (3)	0.010 (13)*	0.50
H81C	0.255 (8)	0.126 (9)	0.130 (3)	0.017 (14)*	0.50
H81D	0.180 (11)	0.198 (16)	0.140 (5)	0.08 (3)*	0.50
H81E	0.325 (6)	0.154 (9)	0.121 (3)	0.016 (14)*	0.50
H81F	0.270 (12)	0.382 (15)	0.126 (5)	0.08 (3)*	0.50
C9	0.2413 (3)	0.2543 (4)	0.27436 (19)	0.0406 (9)
C10	0.2794 (4)	0.2597 (4)	0.34560 (19)	0.0425 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0307 (15)	0.094 (2)	0.0591 (18)	−0.0043 (11)	0.0018 (12)	−0.0051 (14)
O2	0.0316 (17)	0.148 (4)	0.113 (3)	−0.0074 (16)	0.0077 (17)	−0.020 (2)
O6	0.0321 (15)	0.072 (2)	0.078 (2)	−0.0005 (11)	−0.0045 (14)	−0.0065 (14)
C2	0.033 (2)	0.079 (3)	0.083 (3)	0.0036 (17)	0.015 (2)	0.005 (2)
C3	0.036 (3)	0.121 (6)	0.067 (4)	0.010 (3)	0.022 (2)	−0.014 (4)
C3'	0.110 (18)	0.059 (13)	0.081 (16)	−0.066 (13)	0.040 (14)	−0.043 (12)
C4	0.052 (2)	0.090 (3)	0.052 (2)	0.008 (2)	0.0169 (19)	0.004 (2)
C41	0.143 (11)	0.25 (2)	0.091 (8)	0.101 (12)	0.043 (7)	−0.031 (9)
C42	0.074 (5)	0.141 (7)	0.088 (6)	−0.002 (5)	0.023 (5)	0.049 (6)
C5	0.044 (2)	0.0422 (19)	0.043 (2)	0.0014 (14)	0.0005 (15)	−0.0018 (14)
C51	0.065 (3)	0.107 (4)	0.047 (3)	0.007 (2)	−0.010 (2)	−0.001 (2)
C6	0.0288 (17)	0.0368 (17)	0.059 (2)	−0.0004 (12)	−0.0003 (15)	−0.0049 (14)
C7	0.0364 (18)	0.0297 (16)	0.052 (2)	−0.0004 (12)	0.0083 (15)	−0.0029 (13)
C71	0.042 (2)	0.048 (2)	0.067 (3)	0.0064 (16)	0.0184 (19)	0.0049 (19)
C8	0.0384 (19)	0.0377 (17)	0.044 (2)	−0.0018 (13)	0.0053 (15)	−0.0023 (14)
C81	0.053 (3)	0.068 (3)	0.044 (2)	0.001 (2)	0.0033 (19)	−0.003 (2)
C9	0.0297 (17)	0.0473 (19)	0.045 (2)	0.0018 (13)	0.0018 (14)	0.0051 (14)
C10	0.0390 (19)	0.0443 (19)	0.045 (2)	0.0003 (13)	0.0075 (15)	0.0010 (14)

Geometric parameters (Å, º)

O1—C2	1.320 (5)	C4—C42	1.540 (9)
O1—C9	1.405 (4)	C4—C41'	1.59 (3)
O2—C2	1.185 (6)	C41—C42'	1.34 (4)
O6—C6	1.368 (4)	C41—C41'	1.93 (4)
C2—C3	1.492 (8)	C41'—C42	1.04 (3)
C2—C3'	1.63 (3)	C5—C6	1.394 (5)
C3—C42'	1.41 (3)	C5—C10	1.396 (5)
C3—C3'	1.50 (2)	C5—C51	1.513 (5)
C3—C4	1.522 (7)	C6—C7	1.400 (5)
C3'—C42	1.47 (3)	C7—C8	1.385 (5)
C3'—C4	1.59 (2)	C7—C71	1.501 (5)
C4—C42'	1.51 (3)	C8—C9	1.392 (5)
C4—C10	1.534 (5)	C8—C81	1.495 (5)
C4—C41	1.546 (18)	C9—C10	1.384 (5)
C2—O1—C9	122.6 (3)	C3—C4—C3'	57.5 (12)
O2—C2—O1	119.0 (5)	C10—C4—C3'	106.2 (9)
O2—C2—C3	126.2 (4)	C41—C4—C3'	141.7 (11)
O1—C2—C3	113.8 (4)	C42—C4—C3'	56.0 (11)
O2—C2—C3'	115.3 (8)	C41'—C4—C3'	92.6 (16)
O1—C2—C3'	104.7 (9)	C42'—C41—C4	62.8 (16)
C3—C2—C3'	57.1 (7)	C42'—C41—C41'	110 (2)
C42'—C3—C2	157.6 (13)	C4—C41—C41'	53.1 (12)
C42'—C3—C3'	122.1 (18)	C42—C41'—C4	68.0 (19)
C2—C3—C3'	66.1 (11)	C42—C41'—C41	117 (3)
C42'—C3—C4	62.0 (13)	C4—C41'—C41	51.1 (10)
C2—C3—C4	113.4 (4)	C41'—C42—C3'	131 (2)
C3'—C3—C4	63.5 (11)	C41'—C42—C4	73.1 (18)
C42—C3'—C3	115.1 (14)	C3'—C42—C4	63.7 (7)
C42—C3'—C4	60.3 (11)	C41—C42'—C3	124 (3)
C3—C3'—C4	59.0 (6)	C41—C42'—C4	65.2 (16)
C42—C3'—C2	159.0 (15)	C3—C42'—C4	62.6 (13)
C3—C3'—C2	56.7 (10)	C6—C5—C10	118.9 (3)
C4—C3'—C2	102.8 (11)	C6—C5—C51	116.4 (4)
C42'—C4—C3	55.4 (13)	C10—C5—C51	124.6 (4)
C42'—C4—C10	109.3 (12)	O6—C6—C5	115.5 (4)
C3—C4—C10	107.2 (3)	O6—C6—C7	121.7 (3)
C42'—C4—C41	52.0 (14)	C5—C6—C7	122.8 (3)
C3—C4—C41	104.9 (7)	C8—C7—C6	118.4 (3)
C10—C4—C41	111.7 (8)	C8—C7—C71	122.2 (3)
C42'—C4—C42	140.5 (12)	C6—C7—C71	119.3 (3)
C3—C4—C42	109.8 (5)	C9—C8—C7	118.0 (3)
C10—C4—C42	110.1 (4)	C9—C8—C81	120.0 (3)
C41—C4—C42	112.8 (10)	C7—C8—C81	122.0 (3)
C42'—C4—C41'	120.5 (17)	C8—C9—C10	124.5 (3)
C3—C4—C41'	133.5 (12)	C8—C9—O1	113.0 (3)
C10—C4—C41'	115.7 (12)	C10—C9—O1	122.4 (3)
C41—C4—C41'	75.8 (15)	C9—C10—C5	117.2 (3)
C42—C4—C41'	38.9 (12)	C9—C10—C4	117.2 (3)
C42'—C4—C3'	110.2 (16)	C5—C10—C4	125.5 (4)
C9—O1—C2—O2	−176.3 (4)	C42'—C41—C41'—C42	10 (3)
C9—O1—C2—C3	14.4 (6)	C4—C41—C41'—C42	−19.0 (18)
C9—O1—C2—C3'	−45.8 (7)	C42'—C41—C41'—C4	28.6 (18)
O2—C2—C3—C42'	−144 (4)	C4—C41'—C42—C3'	−28 (2)
O1—C2—C3—C42'	24 (4)	C41—C41'—C42—C3'	−12 (4)
C3'—C2—C3—C42'	117 (4)	C41—C41'—C42—C4	15.8 (15)
O2—C2—C3—C3'	99.1 (11)	C3—C3'—C42—C41'	7 (3)
O1—C2—C3—C3'	−92.6 (11)	C4—C3'—C42—C41'	30 (3)
O2—C2—C3—C4	142.8 (5)	C2—C3'—C42—C41'	69 (5)
O1—C2—C3—C4	−48.8 (6)	C3—C3'—C42—C4	−22.7 (10)
C3'—C2—C3—C4	43.8 (11)	C2—C3'—C42—C4	39 (4)
C42'—C3—C3'—C42	2 (2)	C42'—C4—C42—C41'	−77 (3)
C2—C3—C3'—C42	157.8 (18)	C3—C4—C42—C41'	−135.9 (19)
C4—C3—C3'—C42	23.0 (11)	C10—C4—C42—C41'	106.3 (19)
C42'—C3—C3'—C4	−21.5 (17)	C41—C4—C42—C41'	−19.3 (19)
C2—C3—C3'—C4	134.8 (8)	C3'—C4—C42—C41'	−157 (2)
C42'—C3—C3'—C2	−156.3 (15)	C42'—C4—C42—C3'	81 (2)
C4—C3—C3'—C2	−134.8 (8)	C3—C4—C42—C3'	21.4 (11)
O2—C2—C3'—C42	169 (4)	C10—C4—C42—C3'	−96.4 (11)
O1—C2—C3'—C42	36 (4)	C41—C4—C42—C3'	138.0 (12)
C3—C2—C3'—C42	−73 (4)	C41'—C4—C42—C3'	157 (2)
O2—C2—C3'—C3	−118.1 (6)	C4—C41—C42'—C3	22 (2)
O1—C2—C3'—C3	109.1 (7)	C41'—C41—C42'—C3	−3 (3)
O2—C2—C3'—C4	−156.7 (9)	C41'—C41—C42'—C4	−25.5 (15)
O1—C2—C3'—C4	70.6 (12)	C2—C3—C42'—C41	−107 (4)
C3—C2—C3'—C4	−38.6 (7)	C3'—C3—C42'—C41	−1 (3)
C2—C3—C4—C42'	155.6 (15)	C4—C3—C42'—C41	−23 (2)
C3'—C3—C4—C42'	−159.5 (17)	C2—C3—C42'—C4	−84 (4)
C42'—C3—C4—C10	−101.9 (14)	C3'—C3—C42'—C4	21.8 (17)
C2—C3—C4—C10	53.6 (6)	C3—C4—C42'—C41	159 (2)
C3'—C3—C4—C10	98.6 (10)	C10—C4—C42'—C41	−102.9 (14)
C42'—C3—C4—C41	16.9 (17)	C42—C4—C42'—C41	80 (2)
C2—C3—C4—C41	172.5 (9)	C41'—C4—C42'—C41	35 (2)
C3'—C3—C4—C41	−142.5 (13)	C3'—C4—C42'—C41	140.7 (15)
C42'—C3—C4—C42	138.4 (15)	C10—C4—C42'—C3	98.0 (9)
C2—C3—C4—C42	−66.0 (6)	C41—C4—C42'—C3	−159 (2)
C3'—C3—C4—C42	−21.0 (10)	C42—C4—C42'—C3	−79 (2)
C42'—C3—C4—C41'	101 (2)	C41'—C4—C42'—C3	−124.3 (16)
C2—C3—C4—C41'	−103.0 (18)	C3'—C4—C42'—C3	−18.4 (16)
C3'—C3—C4—C41'	−58 (2)	C10—C5—C6—O6	178.8 (3)
C42'—C3—C4—C3'	159.5 (17)	C51—C5—C6—O6	−2.9 (4)
C2—C3—C4—C3'	−45.0 (10)	C10—C5—C6—C7	−0.6 (4)
C42—C3'—C4—C42'	−138.0 (15)	C51—C5—C6—C7	177.8 (3)
C3—C3'—C4—C42'	17.9 (15)	O6—C6—C7—C8	178.9 (3)
C2—C3'—C4—C42'	55.4 (18)	C5—C6—C7—C8	−1.8 (4)
C42—C3'—C4—C3	−156.0 (11)	O6—C6—C7—C71	1.0 (4)
C2—C3'—C4—C3	37.5 (9)	C5—C6—C7—C71	−179.7 (3)
C42—C3'—C4—C10	103.6 (7)	C6—C7—C8—C9	1.3 (4)
C3—C3'—C4—C10	−100.4 (7)	C71—C7—C8—C9	179.2 (3)
C2—C3'—C4—C10	−62.9 (13)	C6—C7—C8—C81	−178.8 (3)
C42—C3'—C4—C41	−84 (2)	C71—C7—C8—C81	−1.0 (5)
C3—C3'—C4—C41	72 (2)	C7—C8—C9—C10	1.6 (5)
C2—C3'—C4—C41	109.1 (18)	C81—C8—C9—C10	−178.3 (3)
C3—C3'—C4—C42	156.0 (11)	C7—C8—C9—O1	−176.5 (3)
C2—C3'—C4—C42	−166.5 (17)	C81—C8—C9—O1	3.6 (4)
C42—C3'—C4—C41'	−14.1 (14)	C2—O1—C9—C8	−169.4 (3)
C3—C3'—C4—C41'	141.9 (13)	C2—O1—C9—C10	12.5 (5)
C2—C3'—C4—C41'	179.4 (16)	C8—C9—C10—C5	−3.9 (5)
C3—C4—C41—C42'	−17.7 (18)	O1—C9—C10—C5	174.0 (3)
C10—C4—C41—C42'	98.1 (16)	C8—C9—C10—C4	178.3 (3)
C42—C4—C41—C42'	−137.2 (16)	O1—C9—C10—C4	−3.8 (5)
C41'—C4—C41—C42'	−150 (2)	C6—C5—C10—C9	3.3 (4)
C3'—C4—C41—C42'	−74 (3)	C51—C5—C10—C9	−174.9 (3)
C42'—C4—C41—C41'	150 (2)	C6—C5—C10—C4	−179.1 (3)
C3—C4—C41—C41'	131.8 (12)	C51—C5—C10—C4	2.7 (5)
C10—C4—C41—C41'	−112.4 (13)	C42'—C4—C10—C9	−86.5 (14)
C42—C4—C41—C41'	12.4 (12)	C3—C4—C10—C9	−27.9 (5)
C3'—C4—C41—C41'	76 (2)	C41—C4—C10—C9	−142.3 (9)
C42'—C4—C41'—C42	134.1 (19)	C42—C4—C10—C9	91.5 (5)
C3—C4—C41'—C42	64 (2)	C41'—C4—C10—C9	133.5 (14)
C10—C4—C41'—C42	−90.7 (17)	C3'—C4—C10—C9	32.4 (12)
C41—C4—C41'—C42	161.7 (18)	C42'—C4—C10—C5	95.9 (14)
C3'—C4—C41'—C42	18.7 (18)	C3—C4—C10—C5	154.5 (4)
C42'—C4—C41'—C41	−27.6 (18)	C41—C4—C10—C5	40.1 (9)
C3—C4—C41'—C41	−97.2 (14)	C42—C4—C10—C5	−86.1 (6)
C10—C4—C41'—C41	107.6 (9)	C41'—C4—C10—C5	−44.1 (15)
C42—C4—C41'—C41	−161.7 (18)	C3'—C4—C10—C5	−145.2 (12)
C3'—C4—C41'—C41	−143.0 (11)