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Acta Cryst. (2011). E67, o1067-o1068    [ doi:10.1107/S1600536811011925 ]

N,N-Diethyl-4-[9-methoxy-6-(4-methoxyphenyl)-5-methyl-2-phenyl-2H-benzo[h]chromen-2-yl]aniline

M.-H. Kim, H.-M. Park and C.-H. Kim

Abstract top

In the title compound, C38H37NO3, the pyran ring has an envelope conformation with the quaternary Cq atom as the flap atom. The dihedral angle formed between the methoxyphenyl group and the naphthalene ring system is 67.32 (6)°. The ethylamino groups lie to the same side of the plane through the phenyl ring and form dihedral angles of 84.6 (3) and 75.8 (2)° with it.

Comment top

The synthesis and applications of the organic photochromic and thermochromic dyes has become of great interest (Kumar et al., 1995; Gemert & Selvig, 2000; Nelson et al., 2002; Gabbutt et al., 2003, 2004). For example, they may be useful as optical transmission materials for ophthalmic glasses and lenses. They also have potential use for optical storage of optical disks or memories (Crano & Guglielmetti, 1999). In particular, benzo- and naphtho-pyrans have been commercialized as photochromic plastic sunglasses in the early 1990's. In our group, research has focused on the development of novel photochromic benzo- and naphtho-pyrans (Kim et al., 2010, 2011; Do et al., 2011). Herein, we report the crystal structure of N,N-diethyl-4-(9-methoxy-6-(4-methoxyphenyl)-5-methyl-2-phenyl-2H- benzo[h]chromene-2-yl)benzenamine (Fig. 1) as a new photochromic material. The –C2—O1—C12—C11—C4—C3- pyran ring has an envelope conformation with the quaternary C2 atom out of the plane, the dihedral angle is 38.7 (2)°, C2—O1 is 1.456 (3) Å and C2—C3 is 1.506 (3) Å. The dihedral angle formed between the methoxyphenyl group and the naphthalen ring of the naphthopyran substituent is 67.32 (6) °. The ethylamino groups of the diethylaminophenyl substituent form dihedral angles of 75.8 (2) and 84.6 (3) ° with the plane through the phenyl ring.

Related literature top

For the synthesis and structures of photochromic benzo- and naphthopyrans, see: Kim et al. (2010, 2011); Do et al. (2011). For the synthesis and applications of organic photochromic and thermochromic dyes, see: Kumar et al. (1995); Crano & Guglielmetti (1999); Gabbutt et al. (2003, 2004); Gemert & Selvig (2000); Nelson et al. (2002).

Experimental top

A solution of 7-methoxy-4-(4-methoxyphenyl)-3-methylnaphthalen-1-ol (10 g, 0.04 mol) and 1-(4-diethylaminophenyl)-1-phenylprop-2-yn-1-ol (11.18 g, 0.04 mol) in anhydrous toluene (500 ml) containing acidic alumina (32.6 g, 0.32 mol) was refluxed for 4 h. The cooled resulting solution was filtered and the alumina residue washed well with toluene. The organic layer was washed with aqueous NaOH and extracted with ethyl acetate (350 ml) and washed with water. The extracts were dried with anhydrous MgSO4 and evaporated to give a crude orange oil. This was purified by silica gel column chromatograpy using 10% ethyl acetate/15% toluene in hexane as eluent. The purified yellow oil was solidified on trituration with ethyl ether. The solid obtained was suction filtered, washed with ethyl ether and air dried (yield: 6.2 g, 28%). Single crystals were obtained by recrystallization from its ethyl acetate solution.

Refinement top

Carbon-bound H-atoms were placed in their calculated positions (C-H = 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl-C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of molecule of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 25% probability level. H atoms are presented as a small spheres of arbitrary radius.
N,N-Diethyl-4-[9-methoxy-6-(4-methoxyphenyl)-5-methyl-2-phenyl- 2H-benzo[h]chromene-2-yl]aniline top
Crystal data top
C38H37NO3Z = 2
Mr = 555.69F(000) = 592
Triclinic, P1Dx = 1.200 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.0527 (3) ÅCell parameters from 1662 reflections
b = 11.6870 (3) Åθ = 2.4–18.2°
c = 12.2752 (3) ŵ = 0.08 mm−1
α = 102.104 (2)°T = 296 K
β = 93.012 (2)°Block, silver
γ = 95.929 (2)°0.20 × 0.18 × 0.07 mm
V = 1537.58 (7) Å3
Data collection top
Bruker APEXII CCD
diffractometer		2360 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
graphiteθmax = 28.5°, θmin = 1.7°
φ and ω scansh = −11→14
28232 measured reflectionsk = −11→15
7658 independent reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.0678P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
7658 reflectionsΔρmax = 0.17 e Å−3
381 parametersΔρmin = −0.16 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0110 (16)
Crystal data top
C38H37NO3γ = 95.929 (2)°
Mr = 555.69V = 1537.58 (7) Å3
Triclinic, P1Z = 2
a = 11.0527 (3) ÅMo Kα radiation
b = 11.6870 (3) ŵ = 0.08 mm−1
c = 12.2752 (3) ÅT = 296 K
α = 102.104 (2)°0.20 × 0.18 × 0.07 mm
β = 93.012 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2360 reflections with I > 2σ(I)
28232 measured reflectionsRint = 0.091
7658 independent reflectionsθmax = 28.5°
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.181Δρmax = 0.17 e Å−3
S = 0.92Δρmin = −0.16 e Å−3
7658 reflectionsAbsolute structure: ?
381 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.82318 (17)0.35611 (16)0.23249 (14)0.0615 (6)
C20.9480 (3)0.3713 (2)0.2008 (2)0.0554 (8)
C30.9498 (3)0.3032 (3)0.0823 (2)0.0661 (9)
H3A1.00160.33150.03420.079*
C40.8776 (3)0.2030 (3)0.0465 (2)0.0645 (8)
H4A0.88140.1596−0.02570.077*
C50.7291 (3)0.0441 (2)0.0983 (2)0.0572 (8)
C60.6450 (3)0.0136 (2)0.1700 (2)0.0558 (8)
C70.5308 (3)0.0780 (3)0.3385 (2)0.0661 (9)
H7A0.48570.00400.32530.079*
C80.5107 (3)0.1610 (3)0.4293 (3)0.0701 (9)
H8A0.45340.14260.47760.084*
C90.5755 (3)0.2747 (3)0.4509 (2)0.0641 (8)
C100.6585 (3)0.3025 (2)0.3801 (2)0.0613 (8)
H10A0.70050.37790.39350.074*
C110.7918 (3)0.1603 (3)0.1200 (2)0.0561 (8)
C120.7684 (3)0.2420 (2)0.2116 (2)0.0557 (8)
C130.6185 (2)0.1013 (2)0.2638 (2)0.0560 (8)
C140.6808 (2)0.2169 (2)0.2862 (2)0.0554 (8)
C150.9789 (3)0.5028 (3)0.2099 (2)0.0553 (8)
C160.8919 (3)0.5786 (3)0.2070 (2)0.0631 (8)
H16A0.80990.54860.19870.076*
C170.9231 (3)0.6986 (3)0.2159 (2)0.0621 (8)
H17A0.86170.74680.21310.075*
C181.0442 (3)0.7479 (3)0.2291 (2)0.0567 (8)
C191.1317 (3)0.6707 (3)0.2304 (3)0.0724 (9)
H19A1.21390.69980.23790.087*
C201.0988 (3)0.5522 (3)0.2210 (2)0.0701 (9)
H20A1.15990.50340.22210.084*
N211.0794 (2)0.8671 (2)0.23776 (19)0.0649 (7)
C220.9879 (3)0.9483 (3)0.2335 (2)0.0752 (9)
H22A0.92140.90840.17980.090*
H22B1.02441.01480.20600.090*
C230.9360 (3)0.9942 (3)0.3426 (3)0.0904 (11)
H23A0.87681.04610.33160.136*
H23B1.00041.03650.39590.136*
H23C0.89770.92940.37000.136*
C241.2021 (3)0.9184 (3)0.2814 (3)0.0767 (10)
H24A1.21360.99920.27230.092*
H24B1.25990.87560.23720.092*
C251.2312 (3)0.9176 (3)0.4035 (3)0.0969 (11)
H25A1.31350.95280.42610.145*
H25B1.22240.83790.41320.145*
H25C1.17600.96170.44840.145*
C261.0304 (3)0.3294 (2)0.2838 (3)0.0601 (8)
C271.0090 (3)0.3521 (3)0.3961 (3)0.0795 (10)
H27A0.93990.38680.41890.095*
C281.0877 (5)0.3243 (4)0.4747 (3)0.1048 (13)
H28A1.07090.33930.54940.126*
C291.1913 (5)0.2744 (3)0.4426 (4)0.1074 (14)
H29A1.24460.25580.49580.129*
C301.2159 (4)0.2522 (3)0.3323 (4)0.0959 (12)
H30A1.28690.22040.31080.115*
C311.1345 (3)0.2773 (3)0.2529 (3)0.0772 (10)
H31A1.14980.25890.17790.093*
C320.7596 (3)−0.0455 (3)−0.0027 (2)0.0748 (9)
H32A0.7356−0.12370.00740.112*
H32B0.8458−0.0354−0.01040.112*
H32C0.7166−0.0339−0.06870.112*
C330.5811 (3)−0.1077 (3)0.1530 (2)0.0569 (8)
C340.6030 (3)−0.1781 (3)0.2284 (2)0.0653 (9)
H34A0.6588−0.14850.28980.078*
C350.5437 (3)−0.2912 (3)0.2146 (3)0.0720 (9)
H35A0.5607−0.33690.26580.086*
C360.4591 (3)−0.3361 (3)0.1245 (3)0.0649 (9)
C370.4360 (3)−0.2686 (3)0.0496 (3)0.0766 (10)
H37A0.3796−0.2981−0.01140.092*
C380.4964 (3)−0.1562 (3)0.0642 (3)0.0740 (9)
H38A0.4794−0.11140.01220.089*
O390.4055 (2)−0.44842 (19)0.11944 (19)0.0864 (7)
C400.3228 (3)−0.5006 (3)0.0241 (3)0.0993 (12)
H40A0.2913−0.57880.02940.149*
H40B0.3651−0.5043−0.04260.149*
H40C0.2567−0.45380.02180.149*
O410.54847 (19)0.34888 (19)0.54643 (16)0.0835 (7)
C420.6237 (3)0.4591 (3)0.5807 (3)0.0965 (12)
H42A0.59590.50330.64780.145*
H42B0.61900.50270.52280.145*
H42C0.70660.44520.59450.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0663 (14)0.0527 (13)0.0626 (12)−0.0051 (11)0.0187 (10)0.0084 (10)
C20.059 (2)0.052 (2)0.0522 (17)−0.0041 (16)0.0157 (15)0.0075 (14)
C30.074 (2)0.065 (2)0.0551 (18)−0.0070 (18)0.0164 (16)0.0067 (16)
C40.078 (2)0.061 (2)0.0502 (17)−0.0023 (18)0.0116 (16)0.0049 (15)
C50.063 (2)0.056 (2)0.0482 (17)0.0010 (16)0.0037 (15)0.0042 (14)
C60.0562 (19)0.053 (2)0.0548 (17)−0.0035 (15)0.0010 (15)0.0104 (15)
C70.062 (2)0.063 (2)0.069 (2)−0.0065 (16)0.0144 (17)0.0091 (17)
C80.064 (2)0.068 (2)0.078 (2)−0.0015 (18)0.0227 (17)0.0151 (18)
C90.065 (2)0.064 (2)0.0604 (19)0.0020 (18)0.0162 (17)0.0058 (16)
C100.066 (2)0.055 (2)0.0598 (18)−0.0054 (16)0.0141 (16)0.0089 (16)
C110.059 (2)0.055 (2)0.0516 (17)−0.0028 (16)0.0062 (15)0.0105 (15)
C120.063 (2)0.0472 (19)0.0537 (17)−0.0017 (16)0.0024 (15)0.0089 (15)
C130.056 (2)0.056 (2)0.0544 (17)−0.0016 (16)0.0055 (15)0.0133 (15)
C140.0537 (19)0.053 (2)0.0553 (17)−0.0033 (15)0.0076 (15)0.0070 (15)
C150.061 (2)0.052 (2)0.0531 (17)0.0017 (18)0.0108 (15)0.0109 (14)
C160.060 (2)0.062 (2)0.0596 (18)−0.0054 (19)0.0040 (15)0.0025 (15)
C170.066 (2)0.057 (2)0.0609 (19)0.0090 (18)0.0035 (16)0.0087 (15)
C180.067 (2)0.047 (2)0.0551 (17)−0.0009 (19)0.0166 (15)0.0112 (14)
C190.062 (2)0.056 (2)0.100 (2)0.0016 (19)0.0219 (18)0.0188 (18)
C200.060 (2)0.055 (2)0.096 (2)0.0036 (18)0.0186 (18)0.0155 (17)
N210.073 (2)0.0515 (17)0.0709 (16)0.0042 (16)0.0119 (14)0.0152 (13)
C220.095 (3)0.058 (2)0.075 (2)0.007 (2)0.0074 (19)0.0198 (17)
C230.098 (3)0.085 (3)0.083 (2)0.017 (2)0.011 (2)0.0035 (19)
C240.085 (3)0.056 (2)0.089 (3)−0.0055 (18)0.018 (2)0.0171 (18)
C250.085 (3)0.104 (3)0.098 (3)−0.003 (2)0.003 (2)0.022 (2)
C260.068 (2)0.0423 (18)0.065 (2)−0.0039 (16)0.0014 (17)0.0066 (15)
C270.097 (3)0.076 (2)0.064 (2)0.005 (2)0.000 (2)0.0158 (19)
C280.134 (4)0.095 (3)0.081 (3)0.003 (3)−0.011 (3)0.020 (2)
C290.132 (4)0.072 (3)0.114 (4)−0.004 (3)−0.037 (3)0.030 (3)
C300.097 (3)0.059 (2)0.126 (4)0.009 (2)−0.018 (3)0.014 (2)
C310.083 (3)0.054 (2)0.090 (2)0.0064 (19)0.003 (2)0.0066 (18)
C320.092 (2)0.067 (2)0.0597 (18)0.0008 (18)0.0116 (17)0.0022 (16)
C330.059 (2)0.052 (2)0.0575 (18)−0.0002 (16)0.0043 (15)0.0108 (16)
C340.066 (2)0.063 (2)0.0611 (19)−0.0094 (17)0.0018 (15)0.0092 (17)
C350.084 (2)0.065 (2)0.067 (2)−0.0055 (19)0.0119 (18)0.0188 (17)
C360.063 (2)0.054 (2)0.073 (2)−0.0048 (18)0.0151 (18)0.0062 (18)
C370.080 (2)0.065 (2)0.076 (2)−0.007 (2)−0.0109 (18)0.0072 (19)
C380.079 (2)0.059 (2)0.078 (2)−0.0061 (18)−0.0090 (18)0.0115 (17)
O390.0922 (17)0.0628 (16)0.0942 (16)−0.0195 (13)0.0114 (13)0.0068 (12)
C400.093 (3)0.077 (3)0.107 (3)−0.024 (2)0.010 (2)−0.012 (2)
O410.0940 (17)0.0751 (16)0.0749 (14)−0.0036 (13)0.0343 (12)0.0015 (12)
C420.108 (3)0.078 (3)0.086 (2)−0.019 (2)0.023 (2)−0.0117 (19)
Geometric parameters (Å, °) top
O1—C121.373 (3)C23—H23A0.9600
O1—C21.456 (3)C23—H23B0.9600
C2—C31.506 (3)C23—H23C0.9600
C2—C151.518 (4)C24—C251.518 (4)
C2—C261.521 (4)C24—H24A0.9700
C3—C41.325 (3)C24—H24B0.9700
C3—H3A0.9300C25—H25A0.9600
C4—C111.464 (4)C25—H25B0.9600
C4—H4A0.9300C25—H25C0.9600
C5—C61.383 (3)C26—C271.385 (4)
C5—C111.424 (4)C26—C311.390 (4)
C5—C321.523 (3)C27—C281.376 (5)
C6—C131.437 (3)C27—H27A0.9300
C6—C331.486 (4)C28—C291.377 (5)
C7—C81.360 (4)C28—H28A0.9300
C7—C131.414 (3)C29—C301.371 (5)
C7—H7A0.9300C29—H29A0.9300
C8—C91.409 (4)C30—C311.389 (4)
C8—H8A0.9300C30—H30A0.9300
C9—C101.357 (3)C31—H31A0.9300
C9—O411.371 (3)C32—H32A0.9600
C10—C141.410 (3)C32—H32B0.9600
C10—H10A0.9300C32—H32C0.9600
C11—C121.369 (3)C33—C381.382 (4)
C12—C141.418 (3)C33—C341.388 (4)
C13—C141.416 (3)C34—C351.386 (4)
C15—C201.377 (4)C34—H34A0.9300
C15—C161.377 (4)C35—C361.386 (4)
C16—C171.388 (4)C35—H35A0.9300
C16—H16A0.9300C36—C371.362 (4)
C17—C181.389 (4)C36—O391.371 (3)
C17—H17A0.9300C37—C381.383 (4)
C18—N211.388 (3)C37—H37A0.9300
C18—C191.390 (4)C38—H38A0.9300
C19—C201.374 (4)O39—C401.431 (3)
C19—H19A0.9300C40—H40A0.9600
C20—H20A0.9300C40—H40B0.9600
N21—C241.452 (4)C40—H40C0.9600
N21—C221.462 (3)O41—C421.429 (3)
C22—C231.501 (4)C42—H42A0.9600
C22—H22A0.9700C42—H42B0.9600
C22—H22B0.9700C42—H42C0.9600
C12—O1—C2115.6 (2)H23A—C23—H23B109.5
O1—C2—C3107.5 (2)C22—C23—H23C109.5
O1—C2—C15105.6 (2)H23A—C23—H23C109.5
C3—C2—C15111.6 (2)H23B—C23—H23C109.5
O1—C2—C26108.2 (2)N21—C24—C25114.4 (2)
C3—C2—C26113.4 (2)N21—C24—H24A108.7
C15—C2—C26110.1 (2)C25—C24—H24A108.7
C4—C3—C2120.1 (3)N21—C24—H24B108.7
C4—C3—H3A119.9C25—C24—H24B108.7
C2—C3—H3A119.9H24A—C24—H24B107.6
C3—C4—C11120.3 (3)C24—C25—H25A109.5
C3—C4—H4A119.8C24—C25—H25B109.5
C11—C4—H4A119.8H25A—C25—H25B109.5
C6—C5—C11120.1 (2)C24—C25—H25C109.5
C6—C5—C32121.3 (3)H25A—C25—H25C109.5
C11—C5—C32118.6 (3)H25B—C25—H25C109.5
C5—C6—C13119.3 (3)C27—C26—C31117.6 (3)
C5—C6—C33121.9 (3)C27—C26—C2120.0 (3)
C13—C6—C33118.8 (2)C31—C26—C2122.1 (3)
C8—C7—C13121.6 (3)C28—C27—C26121.5 (4)
C8—C7—H7A119.2C28—C27—H27A119.3
C13—C7—H7A119.2C26—C27—H27A119.3
C7—C8—C9120.9 (3)C27—C28—C29120.0 (4)
C7—C8—H8A119.6C27—C28—H28A120.0
C9—C8—H8A119.6C29—C28—H28A120.0
C10—C9—O41125.3 (3)C30—C29—C28120.0 (4)
C10—C9—C8119.9 (3)C30—C29—H29A120.0
O41—C9—C8114.8 (3)C28—C29—H29A120.0
C9—C10—C14119.8 (3)C29—C30—C31119.8 (4)
C9—C10—H10A120.1C29—C30—H30A120.1
C14—C10—H10A120.1C31—C30—H30A120.1
C12—C11—C5119.9 (3)C30—C31—C26121.1 (3)
C12—C11—C4115.7 (3)C30—C31—H31A119.5
C5—C11—C4124.3 (3)C26—C31—H31A119.5
C11—C12—O1121.5 (3)C5—C32—H32A109.5
C11—C12—C14122.5 (3)C5—C32—H32B109.5
O1—C12—C14115.8 (2)H32A—C32—H32B109.5
C7—C13—C14116.4 (3)C5—C32—H32C109.5
C7—C13—C6122.7 (3)H32A—C32—H32C109.5
C14—C13—C6120.9 (3)H32B—C32—H32C109.5
C10—C14—C13121.4 (3)C38—C33—C34116.4 (3)
C10—C14—C12121.4 (3)C38—C33—C6122.8 (3)
C13—C14—C12117.2 (3)C34—C33—C6120.7 (3)
C20—C15—C16116.4 (3)C35—C34—C33121.7 (3)
C20—C15—C2120.4 (3)C35—C34—H34A119.2
C16—C15—C2123.3 (3)C33—C34—H34A119.2
C15—C16—C17121.9 (3)C36—C35—C34120.0 (3)
C15—C16—H16A119.0C36—C35—H35A120.0
C17—C16—H16A119.0C34—C35—H35A120.0
C16—C17—C18121.3 (3)C37—C36—O39125.6 (3)
C16—C17—H17A119.4C37—C36—C35119.4 (3)
C18—C17—H17A119.4O39—C36—C35115.0 (3)
N21—C18—C17123.1 (3)C36—C37—C38119.9 (3)
N21—C18—C19120.3 (3)C36—C37—H37A120.0
C17—C18—C19116.6 (3)C38—C37—H37A120.0
C20—C19—C18121.2 (3)C33—C38—C37122.6 (3)
C20—C19—H19A119.4C33—C38—H38A118.7
C18—C19—H19A119.4C37—C38—H38A118.7
C19—C20—C15122.7 (3)C36—O39—C40116.8 (3)
C19—C20—H20A118.7O39—C40—H40A109.5
C15—C20—H20A118.7O39—C40—H40B109.5
C18—N21—C24120.1 (3)H40A—C40—H40B109.5
C18—N21—C22120.6 (3)O39—C40—H40C109.5
C24—N21—C22117.2 (2)H40A—C40—H40C109.5
N21—C22—C23115.4 (3)H40B—C40—H40C109.5
N21—C22—H22A108.4C9—O41—C42117.0 (2)
C23—C22—H22A108.4O41—C42—H42A109.5
N21—C22—H22B108.4O41—C42—H42B109.5
C23—C22—H22B108.4H42A—C42—H42B109.5
H22A—C22—H22B107.5O41—C42—H42C109.5
C22—C23—H23A109.5H42A—C42—H42C109.5
C22—C23—H23B109.5H42B—C42—H42C109.5
C12—O1—C2—C349.7 (3)C20—C15—C16—C17−0.8 (4)
C12—O1—C2—C15169.0 (2)C2—C15—C16—C17179.8 (2)
C12—O1—C2—C26−73.1 (3)C15—C16—C17—C18−0.4 (4)
O1—C2—C3—C4−34.5 (4)C16—C17—C18—N21179.6 (2)
C15—C2—C3—C4−149.9 (3)C16—C17—C18—C191.2 (4)
C26—C2—C3—C485.0 (3)N21—C18—C19—C20−179.5 (3)
C2—C3—C4—C112.7 (4)C17—C18—C19—C20−1.0 (4)
C11—C5—C6—C132.3 (4)C18—C19—C20—C15−0.1 (5)
C32—C5—C6—C13−179.6 (3)C16—C15—C20—C191.0 (4)
C11—C5—C6—C33−177.6 (3)C2—C15—C20—C19−179.5 (3)
C32—C5—C6—C330.5 (4)C17—C18—N21—C24163.0 (3)
C13—C7—C8—C91.1 (5)C19—C18—N21—C24−18.6 (4)
C7—C8—C9—C100.6 (5)C17—C18—N21—C220.1 (4)
C7—C8—C9—O41−178.6 (3)C19—C18—N21—C22178.4 (3)
O41—C9—C10—C14178.0 (3)C18—N21—C22—C2384.6 (3)
C8—C9—C10—C14−1.0 (4)C24—N21—C22—C23−78.8 (3)
C6—C5—C11—C12−0.3 (4)C18—N21—C24—C25−65.8 (4)
C32—C5—C11—C12−178.5 (3)C22—N21—C24—C2597.8 (3)
C6—C5—C11—C4−176.7 (3)O1—C2—C26—C27−38.5 (3)
C32—C5—C11—C45.1 (4)C3—C2—C26—C27−157.6 (3)
C3—C4—C11—C1216.8 (4)C15—C2—C26—C2776.5 (3)
C3—C4—C11—C5−166.6 (3)O1—C2—C26—C31147.3 (2)
C5—C11—C12—O1−177.2 (2)C3—C2—C26—C3128.2 (4)
C4—C11—C12—O1−0.5 (4)C15—C2—C26—C31−97.7 (3)
C5—C11—C12—C14−1.5 (4)C31—C26—C27—C280.1 (5)
C4—C11—C12—C14175.2 (3)C2—C26—C27—C28−174.4 (3)
C2—O1—C12—C11−34.8 (4)C26—C27—C28—C290.9 (5)
C2—O1—C12—C14149.2 (2)C27—C28—C29—C30−0.1 (6)
C8—C7—C13—C14−2.3 (4)C28—C29—C30—C31−1.7 (6)
C8—C7—C13—C6177.3 (3)C29—C30—C31—C262.7 (5)
C5—C6—C13—C7177.8 (3)C27—C26—C31—C30−1.9 (4)
C33—C6—C13—C7−2.3 (4)C2—C26—C31—C30172.4 (3)
C5—C6—C13—C14−2.6 (4)C5—C6—C33—C38−68.0 (4)
C33—C6—C13—C14177.3 (3)C13—C6—C33—C38112.1 (3)
C9—C10—C14—C13−0.2 (4)C5—C6—C33—C34113.1 (3)
C9—C10—C14—C12−178.8 (3)C13—C6—C33—C34−66.8 (4)
C7—C13—C14—C101.8 (4)C38—C33—C34—C350.6 (4)
C6—C13—C14—C10−177.8 (3)C6—C33—C34—C35179.5 (3)
C7—C13—C14—C12−179.5 (3)C33—C34—C35—C36−0.9 (4)
C6—C13—C14—C120.8 (4)C34—C35—C36—C370.7 (4)
C11—C12—C14—C10179.9 (3)C34—C35—C36—O39−179.6 (3)
O1—C12—C14—C10−4.2 (4)O39—C36—C37—C38−180.0 (3)
C11—C12—C14—C131.2 (4)C35—C36—C37—C38−0.3 (4)
O1—C12—C14—C13177.1 (2)C34—C33—C38—C37−0.2 (4)
O1—C2—C15—C20159.1 (2)C6—C33—C38—C37−179.1 (3)
C3—C2—C15—C20−84.4 (3)C36—C37—C38—C330.1 (5)
C26—C2—C15—C2042.5 (3)C37—C36—O39—C403.2 (4)
O1—C2—C15—C16−21.5 (3)C35—C36—O39—C40−176.4 (3)
C3—C2—C15—C1695.1 (3)C10—C9—O41—C42−7.8 (4)
C26—C2—C15—C16−138.1 (3)C8—C9—O41—C42171.3 (3)
references
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Crano, J. C. & Guglielmetti, R. J. (1999). Organic Photochromic and Thermochromic Compounds, Vol 1, edited by J. C. Crano and R. J. Guglielmetti, New York: Plenum Press.

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Gabbutt, C. D., Hepworth, J. D., Heron, B. M., Thomas, D. A., Kilner, C. & Partington, S. M. (2004). Heterocycles, 63, 567–582.

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Nelson, C. M., Chopra, A., Knowles, D. B., Gemert, B. V. & Kumar, A. (2002). US Pat. 6348604 B1.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.