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The title compound, C20H19NO2, crystallizes from an acetone-heptane solution as two dimorphs in the space groups C2/c and Cc. Each dimorph has two mol­ecules in the asymmetric unit. The four mol­ecules adopt slightly different conformations expressed by the degree of bending around a vector connecting the O and C atoms attached to the bridgehead C atom of the pyran ring. Due to the fact that all four mol­ecules are chemically identical, the difference in bending is attributed to packing forces. This is evident from the close contacts of neighbouring mol­ecules perpendicular to the plane of the benzopyran moiety observed in the Cc structure and not in the C2/c structure. These observations provide a unique example that shows how packing forces can affect the conformation of a specific mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108016430/sq3147sup1.cif
Contains datablocks I_C2c, I_Cc, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108016430/sq3147I_C2csup2.hkl
Contains datablock I_C2c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108016430/sq3147I_Ccsup3.hkl
Contains datablock I_Cc

CCDC references: 697578; 697579

Comment top

The design and synthesis of spiropyran derivatives are of great interest in photochemistry (Iyengar & Biewer, 2002; Godzi et al., 2001). For example, we have been interested in testing the photochemical behaviour of a single crystal composed of spiropyran as a guest molecule in inclusion compounds with light-stable host molecules. In the course of our studies, we found that the title compound, (I), crystallizes in two forms corresponding to different molecular conformations and crystal structures. Hence, they may be called conformational polymorphs, a subset of polymorphism in which molecules are folded into different three-dimensional conformations, which can then be packed into alternative crystal structures (Bernstein & Hagler, 1978).

Compound (I) crystallizes as colourless transparent plates in monoclinic space group C2/c, with two molecules, A and B, in the asymmetric unit (Fig. 1), and also as colourless transparent prisms in monoclinic space group Cc, with two molecules, A and B, in the asymmetric unit (Fig. 2). According to the density rule, the more tightly packed crystal with higher density is the more stable (Kitaigorodsky, 1973; Burger & Ramberger, 1979). The density of the spiropyran in the Cc form (1.243 Mg m-3) is slightly higher than that in the C2/c form (1.228 Mg m-3), indicating that it is probably more stable in the acentric space group. However, no experimental effort has been devoted to confirming this assumption.

The four molecules adopt significantly different conformations, expressed by the bending of the benzopyran part of the molecule; Fig. 3 shows the overlap of the four molecules of spiropyran in the two space groups. The molecules were positioned in the overlap diagram in such a way that their indoline parts including tetrahedral sp3 C atoms overlap completely, but the bending of the pyran ring with the aldehyde tail differs significantly in the four cases. The differences between the conformations of the four molecules may be attributed to the different degree of puckering of the pyran ring. Comparison of the angles α between the mean planes through atoms O2/C10/C9 and N1/C10/C11 shows that at the spiro atom, C10, the angles are close to the ideal of 90° (Table 1). At the hetero five-membered ring there is a bending around a vector connecting atoms N1···C11. This bending is expressed by the angles β between the mean planes through atoms N1/C10/C11 and N1/C19–C14/C11. The range of the angles β is too small to explain the differences in the conformation of the four molecules. The angle γ defines the angle between the mean planes through atoms O2/C10/C9 and O2/C5–C7/C2–C4/C8/C9. The γ angles are significantly different in the four molecules and determine the conformational variation. The bending angles in the two molecules that crystallize in space group Cc are different (17.2 and 20.0° in molecules A and B, respectively) and also different from those in the molecules which crystallize in space group C2/c (6.8 and -10.5° in molecules A and B, respectively), which have significantly smaller bending albeit to opposite sides. The bending of the benzopyran in space group C2/c is either towards the N1—C20 bond (molecule B) or towards the C11—C12 bond (molecule A), while in space group Cc the bending is towards the C11—C12 bond in both molecules.

A search of the Cambridge Structural Database (Version?; Allen, 2002) revealed 85 molecules containing a similar benzopyran moiety. In all of them, two methyl groups are bonded to the spiro C atom (C10). It was found that the range of the γ angles is from 0.0° (ZEMHUU; Matsumoto et al., 1995) to 42.2° (WUXGIF; Marek et al., 2003). No correlations were found between the bending angle γ and the bond distances involved with atom O2. Therefore, it is reasonable to assume that the bending does not result from electronic effects.

The differences between the conformations expressed by the degree of bending of the present molecules may be attributed to differences in packing rather than to differences in molecular properties. Close examination of the packing of the different dimorphs was carried out by calculating the intermolecular distances that are shorter than the sum of the Van der Waals radii of the atoms involved. It was shown that in space group Cc, there are several close contacts between the atoms of a neighbouring molecule and atoms belonging to the benzopyran moiety in an almost perpendicular orientation, thus determining the degree of bending (Table 2; Figs. 4b and 4c). In space group C2/c, there is only one such contact (Table 2; Figure 4a). The benzopyran ring is therefore blocked between neighbouring molecules in space group Cc and there is no such blocking in space group C2/c. Furthermore, the carbonyl atom O1 in the dimorph that crystallizes in C2/c is oriented in opposite directions in molecules A and B, while in space group Cc the carbonyl bonds are parallel (torsion angle C3—C2—C1—O1, Table 1). This difference in the orientation of the carbonyl O atom may also help to explain the existence of the dimorphic structures.

Experimental top

1',3'-Dihydro-1',3',3'-trimethyl-spiropyran-6-carbaldehyde was synthesized by the condensation reaction of 1,3,3-trimethyl-2-methylene-indoline and salicylaldehyde in boiling ethanol (Durr & Bouas-Laurent, 1990). After chromatographic purification, the product was recrystallized from an acetone–heptane solution (50:50 v/v) to give colourless crystals of (I) suitable for X-ray analysis.

Refinement top

H atoms were placed at calculated positions [Caromatic—H = 0.93 Å and Uiso(H) = 1.2Ueq(C); Cmethyl—H = 0.96 Å and Uiso(H) = 1.5Ueq(C)] and included as riding atoms. The absolute structure in space group Cc could not be assigned based on Friedel pairs, and the intensity data were merged.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and maXus (Mackay et al., 1998) for I_C2c; SHELXS97 (Sheldrick, 2008) for I_Cc. For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: Please give details.

Figures top
[Figure 1] Fig. 1. The two independent molecules of (I) in the C2/c dimorph; only the atoms of molecule A are labelled. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The two independent molecules of (I) in the Cc dimorph; only the atoms of molecule A are labelled. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. Overlap of two the polymorphs. The two upper aldehyde parts belong to the dimorph in Cc and the two lower parts to that in C2/c.
[Figure 4] Fig. 4. Short intermolecular contacts (dashed lines) directed towards the benzopyran plane. (a) Space group C2/c [symmetry code: (i) 1/2-x, -1/2+y, 1/2-z]. (b) and (c) Space group Cc [symmetry codes: (i) -1/2+x, 1/2+y, z; (ii) 1/2+x, 1/2+y, z; (iii) 1+x, -y, 1/2+z; (iv) 1/2+x, -1/2+y, z].
(I_C2c) 1',3',3'-trimethylspiro[2'H-1-benzopyran-2,2'-indoline]-6-carbaldehyde top
Crystal data top
C20H19NO2F(000) = 2592
Mr = 305.36Dx = 1.228 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5256 reflections
a = 21.447 (4) Åθ = 1.5–27.1°
b = 11.226 (2) ŵ = 0.08 mm1
c = 28.221 (6) ÅT = 293 K
β = 103.57 (2)°Plate, colourless
V = 6605 (2) Å30.05 × 0.04 × 0.02 mm
Z = 16
Data collection top
Nonius Kappa CCD
diffractometer
3291 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 27.1°, θmin = 1.5°
Detector resolution: 95 pixels mm-1h = 2724
ϕ and ω scansk = 1314
15238 measured reflectionsl = 3631
7218 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.089P)2]
where P = (Fo2 + 2Fc2)/3
7218 reflections(Δ/σ)max = 0.001
421 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C20H19NO2V = 6605 (2) Å3
Mr = 305.36Z = 16
Monoclinic, C2/cMo Kα radiation
a = 21.447 (4) ŵ = 0.08 mm1
b = 11.226 (2) ÅT = 293 K
c = 28.221 (6) Å0.05 × 0.04 × 0.02 mm
β = 103.57 (2)°
Data collection top
Nonius Kappa CCD
diffractometer
3291 reflections with I > 2σ(I)
15238 measured reflectionsRint = 0.071
7218 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 0.89Δρmax = 0.24 e Å3
7218 reflectionsΔρmin = 0.20 e Å3
421 parameters
Special details top

Experimental. The X-ray diffraction data were collected at room temperature with Mo Kα radiation (λ = 0.71073 Å). The crystal structure was determined using the MAXUS direct method (Mackay et al., 1998), and refined anisotropically with respect to the non-H atoms using the SHELXL97 program package (Sheldrick, 2008).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1A0.07438 (11)0.21062 (18)0.34421 (6)0.1093 (7)
O2A0.12216 (9)0.05141 (12)0.15604 (5)0.0819 (6)
N1A0.17770 (10)0.20062 (17)0.12514 (6)0.0693 (5)
C1A0.07174 (13)0.1095 (2)0.33030 (8)0.0798 (8)
H1A0.06050.05250.35080.096*
C2A0.08424 (11)0.06607 (19)0.28459 (7)0.0574 (6)
C3A0.08198 (10)0.05404 (18)0.27455 (7)0.0549 (5)
H3A0.07170.10690.29690.066*
C4A0.09458 (11)0.09804 (18)0.23195 (7)0.0541 (5)
C5A0.10878 (11)0.01680 (18)0.19877 (7)0.0555 (6)
C6A0.11080 (12)0.10365 (19)0.20812 (7)0.0664 (7)
H6A0.12010.15680.18540.080*
C7A0.09912 (12)0.14516 (19)0.25103 (7)0.0660 (6)
H7A0.10120.22640.25760.079*
C8A0.09675 (13)0.22299 (19)0.22056 (7)0.0749 (7)
H8A0.08910.27920.24270.090*
C9A0.10943 (14)0.2592 (2)0.17905 (8)0.0849 (9)
H9A0.11240.34070.17410.102*
C10A0.11914 (13)0.17743 (18)0.14011 (7)0.0632 (6)
C11A0.06695 (11)0.18554 (18)0.09119 (7)0.0580 (6)
C12A0.00868 (14)0.1081 (2)0.09050 (10)0.0953 (9)
H12A0.00940.12900.11740.143*
H12B0.02130.02580.09310.143*
H12C0.02270.12040.06050.143*
C13A0.04464 (12)0.3164 (2)0.08107 (8)0.0767 (7)
H13A0.02040.34030.10400.115*
H13B0.01830.32270.04860.115*
H13C0.08140.36710.08430.115*
C14A0.10506 (10)0.15073 (17)0.05525 (7)0.0521 (5)
C15A0.08619 (12)0.11874 (19)0.00716 (7)0.0667 (6)
H15A0.04290.10920.00740.080*
C16A0.13198 (17)0.1005 (2)0.01980 (9)0.0832 (8)
H16A0.11950.07950.05250.100*
C17A0.19535 (17)0.1136 (2)0.00218 (11)0.0918 (9)
H17A0.22560.10150.01620.110*
C18A0.21612 (13)0.1441 (2)0.05043 (10)0.0824 (7)
H18A0.25960.15160.06490.099*
C19A0.16991 (11)0.16328 (18)0.07683 (8)0.0575 (5)
C20A0.23966 (15)0.1915 (3)0.15988 (10)0.1254 (12)
H20A0.23530.21620.19150.188*
H20B0.27020.24180.14960.188*
H20C0.25420.11040.16140.188*
O1B0.08929 (10)0.62079 (19)0.17353 (6)0.1030 (7)
O2B0.15464 (8)0.56029 (12)0.05707 (4)0.0664 (4)
N1B0.10932 (9)0.68521 (15)0.10739 (6)0.0600 (5)
C1B0.09587 (12)0.5361 (3)0.14637 (8)0.0775 (7)
H1B0.08930.46070.16030.093*
C2B0.11347 (10)0.5438 (2)0.09302 (7)0.0558 (5)
C3B0.12856 (10)0.65224 (19)0.06980 (7)0.0579 (6)
H3B0.12890.72040.08850.069*
C4B0.14319 (10)0.66158 (17)0.01951 (7)0.0524 (5)
C5B0.14118 (10)0.55834 (18)0.00758 (6)0.0499 (5)
C6B0.12738 (10)0.44881 (18)0.01482 (7)0.0544 (5)
H6B0.12730.38040.00380.065*
C7B0.11377 (10)0.44203 (19)0.06482 (7)0.0568 (6)
H7B0.10460.36850.08000.068*
C8B0.16039 (12)0.7719 (2)0.00694 (8)0.0727 (7)
H8B0.16470.84110.01020.087*
C9B0.17005 (13)0.7762 (2)0.05470 (8)0.0776 (7)
H9B0.18180.84890.07010.093*
C10B0.16332 (11)0.67164 (18)0.08566 (7)0.0576 (6)
C11B0.22043 (11)0.6468 (2)0.13037 (8)0.0687 (6)
C12B0.27025 (14)0.5628 (3)0.11802 (10)0.1119 (11)
H12D0.28610.59570.09170.168*
H12E0.25090.48670.10850.168*
H12F0.30510.55310.14610.168*
C13B0.25282 (13)0.7640 (3)0.15145 (9)0.0980 (9)
H13D0.27430.79900.12860.147*
H13E0.28350.74790.18150.147*
H13F0.22090.81820.15740.147*
C14B0.18550 (11)0.59669 (19)0.16640 (7)0.0608 (6)
C19B0.12102 (11)0.62226 (17)0.15099 (7)0.0554 (6)
C18B0.07783 (13)0.5924 (2)0.17899 (9)0.0738 (7)
H18B0.03430.60890.16810.089*
C17B0.1012 (2)0.5382 (2)0.22296 (10)0.0928 (10)
H17B0.07300.51800.24220.111*
C15B0.20761 (15)0.5420 (2)0.21114 (9)0.0868 (8)
H15B0.25100.52460.22230.104*
C16B0.1646 (2)0.5133 (2)0.23920 (9)0.0966 (10)
H16B0.17930.47670.26930.116*
C20B0.04514 (13)0.6959 (3)0.07677 (9)0.0950 (9)
H20D0.04640.74250.04850.142*
H20E0.01790.73420.09470.142*
H20F0.02860.61810.06680.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.161 (2)0.0878 (14)0.0885 (12)0.0042 (13)0.0485 (13)0.0277 (11)
O2A0.1491 (17)0.0460 (9)0.0600 (9)0.0011 (9)0.0438 (10)0.0012 (7)
N1A0.0691 (14)0.0745 (13)0.0551 (11)0.0099 (11)0.0042 (10)0.0050 (9)
C1A0.103 (2)0.0719 (18)0.0692 (16)0.0056 (15)0.0291 (15)0.0130 (13)
C2A0.0633 (15)0.0573 (14)0.0508 (12)0.0020 (11)0.0116 (10)0.0016 (10)
C3A0.0578 (14)0.0563 (14)0.0476 (11)0.0076 (10)0.0067 (10)0.0062 (10)
C4A0.0688 (15)0.0463 (12)0.0446 (11)0.0035 (10)0.0077 (10)0.0036 (9)
C5A0.0744 (16)0.0476 (13)0.0438 (11)0.0012 (11)0.0123 (10)0.0003 (9)
C6A0.098 (2)0.0429 (13)0.0622 (14)0.0028 (12)0.0278 (13)0.0045 (10)
C7A0.0903 (19)0.0474 (13)0.0611 (14)0.0031 (12)0.0197 (13)0.0045 (10)
C8A0.124 (2)0.0482 (14)0.0528 (13)0.0034 (14)0.0217 (13)0.0072 (10)
C9A0.147 (3)0.0481 (14)0.0609 (14)0.0003 (15)0.0275 (16)0.0027 (12)
C10A0.0964 (19)0.0436 (13)0.0496 (12)0.0062 (12)0.0175 (12)0.0010 (10)
C11A0.0647 (15)0.0533 (13)0.0581 (13)0.0097 (11)0.0187 (11)0.0046 (10)
C12A0.084 (2)0.097 (2)0.115 (2)0.0311 (16)0.0417 (17)0.0172 (17)
C13A0.0735 (18)0.0759 (17)0.0822 (16)0.0089 (14)0.0211 (13)0.0017 (13)
C14A0.0576 (14)0.0481 (12)0.0486 (12)0.0041 (10)0.0086 (10)0.0010 (9)
C15A0.0772 (17)0.0618 (15)0.0571 (14)0.0018 (12)0.0076 (12)0.0037 (11)
C16A0.124 (3)0.0682 (17)0.0619 (15)0.0005 (17)0.0322 (18)0.0045 (12)
C17A0.115 (3)0.0763 (19)0.102 (2)0.0053 (18)0.062 (2)0.0006 (16)
C18A0.0606 (17)0.0804 (18)0.110 (2)0.0079 (14)0.0278 (16)0.0116 (15)
C19A0.0613 (15)0.0538 (13)0.0561 (13)0.0001 (11)0.0111 (11)0.0057 (10)
C20A0.097 (2)0.156 (3)0.094 (2)0.001 (2)0.0381 (17)0.0049 (19)
O1B0.1279 (18)0.1248 (17)0.0544 (10)0.0154 (13)0.0172 (11)0.0089 (10)
O2B0.1003 (13)0.0525 (9)0.0437 (8)0.0083 (8)0.0116 (8)0.0035 (6)
N1B0.0552 (12)0.0632 (12)0.0601 (11)0.0010 (9)0.0100 (9)0.0002 (9)
C1B0.083 (2)0.099 (2)0.0532 (14)0.0136 (16)0.0223 (13)0.0065 (14)
C2B0.0501 (13)0.0704 (15)0.0483 (12)0.0069 (11)0.0147 (10)0.0046 (11)
C3B0.0587 (15)0.0654 (14)0.0528 (13)0.0018 (11)0.0198 (10)0.0074 (11)
C4B0.0590 (14)0.0486 (13)0.0521 (12)0.0027 (10)0.0182 (10)0.0008 (10)
C5B0.0517 (13)0.0537 (13)0.0446 (11)0.0032 (10)0.0122 (9)0.0017 (9)
C6B0.0604 (14)0.0494 (13)0.0540 (12)0.0054 (10)0.0146 (10)0.0019 (10)
C7B0.0536 (14)0.0615 (14)0.0568 (13)0.0065 (11)0.0160 (10)0.0105 (10)
C8B0.100 (2)0.0552 (15)0.0677 (15)0.0147 (13)0.0293 (14)0.0010 (11)
C9B0.112 (2)0.0558 (15)0.0688 (15)0.0215 (14)0.0291 (14)0.0136 (12)
C10B0.0690 (15)0.0534 (13)0.0508 (12)0.0114 (11)0.0149 (11)0.0113 (10)
C11B0.0549 (15)0.0866 (17)0.0628 (14)0.0067 (13)0.0106 (12)0.0195 (12)
C12B0.072 (2)0.151 (3)0.113 (2)0.0233 (19)0.0200 (17)0.029 (2)
C13B0.078 (2)0.125 (2)0.0886 (17)0.0451 (18)0.0151 (15)0.0313 (16)
C14B0.0674 (17)0.0622 (14)0.0470 (13)0.0034 (12)0.0015 (11)0.0115 (10)
C19B0.0662 (16)0.0479 (13)0.0533 (13)0.0036 (11)0.0166 (12)0.0110 (10)
C18B0.090 (2)0.0574 (14)0.0833 (17)0.0080 (13)0.0389 (16)0.0126 (13)
C17B0.159 (3)0.0602 (17)0.0711 (19)0.027 (2)0.050 (2)0.0178 (14)
C15B0.099 (2)0.0826 (19)0.0623 (16)0.0028 (16)0.0143 (15)0.0124 (13)
C16B0.166 (3)0.0678 (18)0.0476 (15)0.020 (2)0.009 (2)0.0066 (12)
C20B0.0681 (19)0.108 (2)0.0990 (19)0.0171 (16)0.0003 (15)0.0107 (16)
Geometric parameters (Å, º) top
O1A—C1A1.198 (3)O1B—C1B1.209 (3)
O2A—C5A1.360 (2)O2B—C5B1.359 (2)
O2A—C10A1.481 (2)O2B—C10B1.476 (2)
N1A—C19A1.398 (3)N1B—C19B1.390 (3)
N1A—C10A1.440 (3)N1B—C10B1.440 (3)
N1A—C20A1.458 (3)N1B—C20B1.448 (3)
C1A—C2A1.461 (3)C1B—C2B1.466 (3)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C3A1.376 (3)C2B—C3B1.385 (3)
C2A—C7A1.389 (3)C2B—C7B1.391 (3)
C3A—C4A1.384 (3)C3B—C4B1.384 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.391 (3)C4B—C5B1.395 (3)
C4A—C8A1.442 (3)C4B—C8B1.449 (3)
C5A—C6A1.376 (3)C5B—C6B1.383 (3)
C6A—C7A1.374 (3)C6B—C7B1.374 (3)
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.327 (3)C8B—C9B1.316 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.484 (3)C9B—C10B1.491 (3)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.563 (3)C10B—C11B1.564 (3)
C11A—C14A1.496 (3)C11B—C14B1.506 (3)
C11A—C12A1.519 (3)C11B—C12B1.526 (3)
C11A—C13A1.550 (3)C11B—C13B1.541 (3)
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—H13A0.9600C13B—H13D0.9600
C13A—H13B0.9600C13B—H13E0.9600
C13A—H13C0.9600C13B—H13F0.9600
C14A—C15A1.370 (3)C14B—C19B1.379 (3)
C14A—C19A1.388 (3)C14B—C15B1.384 (3)
C15A—C16A1.391 (3)C19B—C18B1.392 (3)
C15A—H15A0.9300C18B—C17B1.367 (4)
C16A—C17A1.363 (4)C18B—H18B0.9300
C16A—H16A0.9300C17B—C16B1.359 (4)
C17A—C18A1.373 (3)C17B—H17B0.9300
C17A—H17A0.9300C15B—C16B1.388 (4)
C18A—C19A1.389 (3)C15B—H15B0.9300
C18A—H18A0.9300C16B—H16B0.9300
C20A—H20A0.9600C20B—H20D0.9600
C20A—H20B0.9600C20B—H20E0.9600
C20A—H20C0.9600C20B—H20F0.9600
C5A—O2A—C10A122.59 (15)C5B—O2B—C10B123.02 (15)
C19A—N1A—C10A108.61 (18)C19B—N1B—C10B109.09 (18)
C19A—N1A—C20A121.1 (2)C19B—N1B—C20B121.29 (19)
C10A—N1A—C20A120.7 (2)C10B—N1B—C20B120.08 (18)
O1A—C1A—C2A126.9 (2)O1B—C1B—C2B124.6 (2)
O1A—C1A—H1A116.5O1B—C1B—H1B117.7
C2A—C1A—H1A116.5C2B—C1B—H1B117.7
C3A—C2A—C7A119.25 (18)C3B—C2B—C7B118.83 (18)
C3A—C2A—C1A120.2 (2)C3B—C2B—C1B120.9 (2)
C7A—C2A—C1A120.5 (2)C7B—C2B—C1B120.3 (2)
C2A—C3A—C4A121.58 (18)C4B—C3B—C2B121.57 (19)
C2A—C3A—H3A119.2C4B—C3B—H3B119.2
C4A—C3A—H3A119.2C2B—C3B—H3B119.2
C3A—C4A—C5A117.97 (19)C3B—C4B—C5B118.07 (18)
C3A—C4A—C8A124.31 (17)C3B—C4B—C8B124.22 (18)
C5A—C4A—C8A117.66 (18)C5B—C4B—C8B117.71 (17)
O2A—C5A—C6A116.54 (17)O2B—C5B—C6B117.10 (17)
O2A—C5A—C4A122.31 (18)O2B—C5B—C4B121.59 (17)
C6A—C5A—C4A121.14 (18)C6B—C5B—C4B121.28 (17)
C7A—C6A—C5A119.86 (19)C7B—C6B—C5B119.33 (18)
C7A—C6A—H6A120.1C7B—C6B—H6B120.3
C5A—C6A—H6A120.1C5B—C6B—H6B120.3
C6A—C7A—C2A120.2 (2)C6B—C7B—C2B120.88 (19)
C6A—C7A—H7A119.9C6B—C7B—H7B119.6
C2A—C7A—H7A119.9C2B—C7B—H7B119.6
C9A—C8A—C4A121.26 (19)C9B—C8B—C4B121.27 (19)
C9A—C8A—H8A119.4C9B—C8B—H8B119.4
C4A—C8A—H8A119.4C4B—C8B—H8B119.4
C8A—C9A—C10A123.9 (2)C8B—C9B—C10B123.9 (2)
C8A—C9A—H9A118.1C8B—C9B—H9B118.0
C10A—C9A—H9A118.1C10B—C9B—H9B118.0
N1A—C10A—O2A106.42 (18)N1B—C10B—O2B108.15 (16)
N1A—C10A—C9A112.9 (2)N1B—C10B—C9B111.37 (19)
O2A—C10A—C9A111.73 (16)O2B—C10B—C9B111.34 (15)
N1A—C10A—C11A102.91 (15)N1B—C10B—C11B103.37 (15)
O2A—C10A—C11A107.16 (17)O2B—C10B—C11B105.35 (17)
C9A—C10A—C11A115.0 (2)C9B—C10B—C11B116.6 (2)
C14A—C11A—C12A114.86 (18)C14B—C11B—C12B114.2 (2)
C14A—C11A—C13A108.46 (16)C14B—C11B—C13B107.99 (17)
C12A—C11A—C13A108.8 (2)C12B—C11B—C13B109.9 (2)
C14A—C11A—C10A101.05 (18)C14B—C11B—C10B101.05 (18)
C12A—C11A—C10A113.24 (18)C12B—C11B—C10B112.57 (18)
C13A—C11A—C10A110.13 (17)C13B—C11B—C10B110.9 (2)
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C11A—C13A—H13A109.5C11B—C13B—H13D109.5
C11A—C13A—H13B109.5C11B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C11A—C13A—H13C109.5C11B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C15A—C14A—C19A119.6 (2)C19B—C14B—C15B118.9 (2)
C15A—C14A—C11A131.2 (2)C19B—C14B—C11B109.29 (19)
C19A—C14A—C11A109.06 (18)C15B—C14B—C11B131.5 (2)
C14A—C15A—C16A119.9 (2)C14B—C19B—N1B110.14 (19)
C14A—C15A—H15A120.1C14B—C19B—C18B121.5 (2)
C16A—C15A—H15A120.1N1B—C19B—C18B128.2 (2)
C17A—C16A—C15A119.4 (2)C17B—C18B—C19B118.1 (3)
C17A—C16A—H16A120.3C17B—C18B—H18B120.9
C15A—C16A—H16A120.3C19B—C18B—H18B120.9
C16A—C17A—C18A122.3 (2)C16B—C17B—C18B121.5 (3)
C16A—C17A—H17A118.8C16B—C17B—H17B119.3
C18A—C17A—H17A118.8C18B—C17B—H17B119.3
C17A—C18A—C19A117.7 (3)C16B—C15B—C14B119.5 (3)
C17A—C18A—H18A121.2C16B—C15B—H15B120.3
C19A—C18A—H18A121.2C14B—C15B—H15B120.3
C14A—C19A—C18A121.1 (2)C17B—C16B—C15B120.4 (3)
C14A—C19A—N1A109.65 (19)C17B—C16B—H16B119.8
C18A—C19A—N1A129.2 (2)C15B—C16B—H16B119.8
N1A—C20A—H20A109.5N1B—C20B—H20D109.5
N1A—C20A—H20B109.5N1B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
N1A—C20A—H20C109.5N1B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
O1A—C1A—C2A—C3A177.2 (3)O1B—C1B—C2B—C3B4.8 (4)
O1A—C1A—C2A—C7A2.2 (4)O1B—C1B—C2B—C7B173.7 (2)
C7A—C2A—C3A—C4A0.4 (3)C7B—C2B—C3B—C4B0.7 (3)
C1A—C2A—C3A—C4A179.0 (2)C1B—C2B—C3B—C4B177.8 (2)
C2A—C3A—C4A—C5A1.0 (3)C2B—C3B—C4B—C5B1.2 (3)
C2A—C3A—C4A—C8A176.2 (2)C2B—C3B—C4B—C8B178.9 (2)
C10A—O2A—C5A—C6A177.3 (2)C10B—O2B—C5B—C6B173.19 (19)
C10A—O2A—C5A—C4A3.5 (3)C10B—O2B—C5B—C4B8.8 (3)
C3A—C4A—C5A—O2A179.6 (2)C3B—C4B—C5B—O2B179.71 (19)
C8A—C4A—C5A—O2A2.3 (3)C8B—C4B—C5B—O2B0.2 (3)
C3A—C4A—C5A—C6A0.6 (3)C3B—C4B—C5B—C6B2.4 (3)
C8A—C4A—C5A—C6A176.8 (2)C8B—C4B—C5B—C6B177.7 (2)
O2A—C5A—C6A—C7A178.7 (2)O2B—C5B—C6B—C7B179.66 (18)
C4A—C5A—C6A—C7A0.5 (4)C4B—C5B—C6B—C7B1.7 (3)
C5A—C6A—C7A—C2A1.1 (4)C5B—C6B—C7B—C2B0.3 (3)
C3A—C2A—C7A—C6A0.6 (4)C3B—C2B—C7B—C6B1.4 (3)
C1A—C2A—C7A—C6A180.0 (2)C1B—C2B—C7B—C6B177.1 (2)
C3A—C4A—C8A—C9A179.7 (2)C3B—C4B—C8B—C9B175.9 (2)
C5A—C4A—C8A—C9A2.5 (4)C5B—C4B—C8B—C9B4.0 (3)
C4A—C8A—C9A—C10A3.1 (4)C4B—C8B—C9B—C10B1.2 (4)
C19A—N1A—C10A—O2A84.07 (19)C19B—N1B—C10B—O2B85.19 (19)
C20A—N1A—C10A—O2A62.3 (3)C20B—N1B—C10B—O2B61.5 (2)
C19A—N1A—C10A—C9A153.01 (19)C19B—N1B—C10B—C9B152.16 (18)
C20A—N1A—C10A—C9A60.6 (3)C20B—N1B—C10B—C9B61.2 (3)
C19A—N1A—C10A—C11A28.5 (2)C19B—N1B—C10B—C11B26.2 (2)
C20A—N1A—C10A—C11A174.8 (2)C20B—N1B—C10B—C11B172.83 (19)
C5A—O2A—C10A—N1A131.9 (2)C5B—O2B—C10B—N1B109.9 (2)
C5A—O2A—C10A—C9A8.3 (3)C5B—O2B—C10B—C9B12.7 (3)
C5A—O2A—C10A—C11A118.5 (2)C5B—O2B—C10B—C11B140.04 (19)
C8A—C9A—C10A—N1A128.0 (3)C8B—C9B—C10B—N1B111.9 (3)
C8A—C9A—C10A—O2A8.1 (4)C8B—C9B—C10B—O2B8.9 (3)
C8A—C9A—C10A—C11A114.3 (3)C8B—C9B—C10B—C11B129.8 (3)
N1A—C10A—C11A—C14A27.63 (19)N1B—C10B—C11B—C14B24.4 (2)
O2A—C10A—C11A—C14A84.35 (18)O2B—C10B—C11B—C14B88.97 (18)
C9A—C10A—C11A—C14A150.80 (19)C9B—C10B—C11B—C14B146.99 (19)
N1A—C10A—C11A—C12A151.00 (19)N1B—C10B—C11B—C12B146.6 (2)
O2A—C10A—C11A—C12A39.0 (2)O2B—C10B—C11B—C12B33.2 (3)
C9A—C10A—C11A—C12A85.8 (2)C9B—C10B—C11B—C12B90.8 (3)
N1A—C10A—C11A—C13A86.9 (2)N1B—C10B—C11B—C13B89.8 (2)
O2A—C10A—C11A—C13A161.11 (16)O2B—C10B—C11B—C13B156.75 (17)
C9A—C10A—C11A—C13A36.3 (3)C9B—C10B—C11B—C13B32.7 (3)
C12A—C11A—C14A—C15A44.1 (3)C12B—C11B—C14B—C19B136.6 (2)
C13A—C11A—C14A—C15A77.9 (3)C13B—C11B—C14B—C19B100.9 (2)
C10A—C11A—C14A—C15A166.3 (2)C10B—C11B—C14B—C19B15.5 (2)
C12A—C11A—C14A—C19A140.6 (2)C12B—C11B—C14B—C15B49.2 (3)
C13A—C11A—C14A—C19A97.4 (2)C13B—C11B—C14B—C15B73.3 (3)
C10A—C11A—C14A—C19A18.4 (2)C10B—C11B—C14B—C15B170.3 (2)
C19A—C14A—C15A—C16A0.8 (3)C15B—C14B—C19B—N1B175.22 (18)
C11A—C14A—C15A—C16A174.1 (2)C11B—C14B—C19B—N1B0.2 (2)
C14A—C15A—C16A—C17A0.6 (4)C15B—C14B—C19B—C18B1.1 (3)
C15A—C16A—C17A—C18A0.2 (4)C11B—C14B—C19B—C18B176.14 (19)
C16A—C17A—C18A—C19A0.9 (4)C10B—N1B—C19B—C14B17.2 (2)
C15A—C14A—C19A—C18A0.1 (3)C20B—N1B—C19B—C14B163.4 (2)
C11A—C14A—C19A—C18A175.87 (19)C10B—N1B—C19B—C18B166.8 (2)
C15A—C14A—C19A—N1A177.72 (18)C20B—N1B—C19B—C18B20.6 (3)
C11A—C14A—C19A—N1A1.8 (2)C14B—C19B—C18B—C17B1.0 (3)
C17A—C18A—C19A—C14A0.7 (3)N1B—C19B—C18B—C17B174.6 (2)
C17A—C18A—C19A—N1A176.4 (2)C19B—C18B—C17B—C16B0.2 (4)
C10A—N1A—C19A—C14A17.8 (2)C19B—C14B—C15B—C16B0.5 (3)
C20A—N1A—C19A—C14A164.0 (2)C11B—C14B—C15B—C16B174.2 (2)
C10A—N1A—C19A—C18A164.9 (2)C18B—C17B—C16B—C15B0.3 (4)
C20A—N1A—C19A—C18A18.7 (4)C14B—C15B—C16B—C17B0.2 (4)
(I_Cc) 1',3',3'-trimethylspiro[2'H-1-benzopyran-2,2'-indoline]-6-carbaldehyde top
Crystal data top
C20H19NO2F(000) = 1296
Mr = 305.36Dx = 1.243 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3372 reflections
a = 11.699 (2) Åθ = 1.7–27.9°
b = 11.692 (2) ŵ = 0.08 mm1
c = 24.406 (5) ÅT = 293 K
β = 102.13 (3)°Prism, white transparent
V = 3263.8 (10) Å30.04 × 0.03 × 0.03 mm
Z = 8
Data collection top
Nonius Kappa CCD
diffractometer
3405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 25.1°, θmin = 1.7°
Detector resolution: 95 pixels mm-1h = 1313
ϕ and ω scansk = 1313
12585 measured reflectionsl = 2929
5001 independent reflections
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0554P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.002
2878 reflectionsΔρmax = 0.12 e Å3
422 parametersΔρmin = 0.13 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0063 (7)
Crystal data top
C20H19NO2V = 3263.8 (10) Å3
Mr = 305.36Z = 8
Monoclinic, CcMo Kα radiation
a = 11.699 (2) ŵ = 0.08 mm1
b = 11.692 (2) ÅT = 293 K
c = 24.406 (5) Å0.04 × 0.03 × 0.03 mm
β = 102.13 (3)°
Data collection top
Nonius Kappa CCD
diffractometer
3405 reflections with I > 2σ(I)
12585 measured reflectionsRint = 0.050
5001 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 0.95Δρmax = 0.12 e Å3
2878 reflectionsΔρmin = 0.13 e Å3
422 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A0.9088 (2)0.4017 (3)0.37760 (12)0.0853 (9)
O2A0.36444 (18)0.3221 (2)0.27965 (8)0.0542 (6)
N1A0.1977 (2)0.2622 (2)0.30947 (11)0.0542 (7)
C1A0.8511 (3)0.3796 (3)0.33103 (17)0.0650 (10)
H1A0.88990.37510.30150.078*
C2A0.7242 (3)0.3597 (3)0.31855 (13)0.0520 (9)
C3A0.6616 (3)0.3600 (3)0.36101 (13)0.0514 (9)
H3A0.70130.36870.39800.062*
C4A0.5416 (3)0.3478 (3)0.34939 (12)0.0466 (8)
C5A0.4840 (3)0.3343 (3)0.29364 (12)0.0458 (8)
C6A0.5452 (3)0.3303 (3)0.25110 (13)0.0531 (9)
H6A0.50590.31920.21420.064*
C7A0.6651 (3)0.3428 (3)0.26380 (13)0.0560 (9)
H7A0.70670.33980.23530.067*
C8A0.4720 (3)0.3466 (3)0.39220 (13)0.0595 (10)
H8A0.50920.34750.42980.071*
C9A0.3566 (3)0.3442 (3)0.37842 (13)0.0624 (10)
H9A0.31550.34040.40710.075*
C10A0.2886 (3)0.3473 (3)0.31955 (12)0.0469 (8)
C11A0.2218 (3)0.4610 (3)0.30049 (12)0.0515 (8)
C12A0.2986 (4)0.5478 (3)0.27834 (18)0.0771 (11)
H12A0.36080.57190.30830.116*
H12B0.25230.61280.26350.116*
H12C0.33090.51320.24930.116*
C13A0.1747 (4)0.5146 (3)0.34909 (16)0.0716 (11)
H13A0.23900.53960.37780.107*
H13B0.12990.45870.36430.107*
H13C0.12580.57880.33540.107*
C19A0.1091 (3)0.2998 (3)0.26586 (12)0.0516 (8)
C18A0.0183 (3)0.2362 (4)0.23463 (15)0.0721 (11)
H18A0.01230.15800.24050.086*
C17A0.0621 (4)0.2919 (6)0.19506 (18)0.0922 (15)
H17A0.12430.25080.17410.111*
C16A0.0539 (4)0.4061 (6)0.18533 (16)0.0899 (15)
H16A0.10890.44120.15730.108*
C15A0.0372 (4)0.4709 (4)0.21741 (15)0.0771 (12)
H15A0.04220.54920.21150.092*
C14A0.1194 (3)0.4162 (3)0.25794 (12)0.0519 (8)
C20A0.2286 (4)0.1418 (3)0.31491 (18)0.0829 (13)
H20A0.28920.13060.34770.124*
H20B0.25590.11730.28240.124*
H20C0.16110.09780.31820.124*
O1B0.1590 (3)0.7190 (3)0.12625 (13)0.0968 (10)
O2B0.15210 (19)0.2171 (2)0.02426 (8)0.0544 (6)
N1B0.2301 (2)0.0354 (3)0.04624 (11)0.0579 (7)
C1B0.1351 (3)0.6808 (4)0.07959 (19)0.0722 (11)
H1B0.10850.73200.05060.087*
C2B0.1442 (3)0.5605 (3)0.06449 (13)0.0547 (9)
C3B0.1856 (3)0.4798 (3)0.10620 (13)0.0551 (9)
H3B0.21150.50440.14300.066*
C4B0.1891 (3)0.3650 (3)0.09425 (12)0.0495 (8)
C5B0.1516 (3)0.3298 (3)0.03872 (12)0.0469 (8)
C6B0.1135 (3)0.4084 (3)0.00392 (12)0.0543 (9)
H6B0.09050.38400.04090.065*
C7B0.1102 (3)0.5227 (3)0.00922 (14)0.0575 (9)
H7B0.08480.57560.01920.069*
C8B0.2329 (3)0.2787 (4)0.13594 (12)0.0606 (10)
H8B0.26680.30090.17230.073*
C9B0.2254 (3)0.1690 (4)0.12306 (13)0.0607 (10)
H9B0.25890.11650.15030.073*
C10B0.1657 (3)0.1250 (3)0.06689 (13)0.0504 (9)
C11B0.0437 (3)0.0691 (3)0.06482 (13)0.0506 (8)
C12B0.0555 (3)0.1571 (3)0.05451 (16)0.0664 (10)
H12D0.04120.21370.08370.100*
H12E0.12840.11930.05450.100*
H12F0.05910.19340.01890.100*
C13B0.0423 (4)0.0025 (3)0.11911 (14)0.0723 (11)
H13D0.05310.05470.15010.109*
H13E0.10430.05280.12540.109*
H13F0.03140.03590.11570.109*
C14B0.0391 (3)0.0162 (3)0.01754 (12)0.0498 (8)
C15B0.0528 (3)0.0781 (3)0.01253 (14)0.0621 (10)
H15B0.12760.06920.00570.074*
C16B0.0327 (4)0.1539 (3)0.05314 (16)0.0721 (11)
H16B0.09440.19600.07380.087*
C17B0.0772 (4)0.1671 (4)0.06288 (15)0.0768 (12)
H17B0.08900.21710.09080.092*
C18B0.1712 (4)0.1079 (3)0.03230 (15)0.0698 (10)
H18B0.24600.11840.03870.084*
C19B0.1506 (3)0.0320 (3)0.00844 (12)0.0524 (9)
C20B0.3474 (3)0.0569 (4)0.03802 (17)0.0823 (12)
H20D0.38890.10330.06810.123*
H20E0.34330.09600.00310.123*
H20F0.38760.01450.03740.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0591 (17)0.103 (2)0.090 (2)0.0002 (16)0.0068 (14)0.0132 (16)
O2A0.0517 (15)0.0700 (16)0.0410 (11)0.0034 (11)0.0103 (10)0.0045 (10)
N1A0.0582 (18)0.0408 (18)0.0661 (16)0.0033 (13)0.0188 (14)0.0031 (13)
C1A0.059 (3)0.059 (3)0.079 (3)0.0088 (19)0.020 (2)0.0120 (19)
C2A0.050 (2)0.045 (2)0.061 (2)0.0073 (16)0.0128 (17)0.0023 (15)
C3A0.051 (2)0.051 (2)0.0502 (18)0.0081 (17)0.0066 (15)0.0021 (15)
C4A0.047 (2)0.047 (2)0.0445 (18)0.0034 (15)0.0066 (14)0.0013 (13)
C5A0.049 (2)0.044 (2)0.0448 (18)0.0041 (15)0.0089 (15)0.0011 (13)
C6A0.061 (3)0.058 (2)0.0429 (17)0.0026 (17)0.0159 (16)0.0032 (14)
C7A0.065 (3)0.048 (2)0.062 (2)0.0088 (18)0.0294 (18)0.0023 (16)
C8A0.058 (3)0.080 (3)0.0393 (17)0.0043 (19)0.0093 (15)0.0031 (15)
C9A0.057 (3)0.087 (3)0.0455 (19)0.0003 (19)0.0146 (16)0.0013 (16)
C10A0.0475 (19)0.053 (2)0.0432 (17)0.0015 (16)0.0155 (13)0.0018 (14)
C11A0.058 (2)0.042 (2)0.0585 (18)0.0020 (17)0.0212 (16)0.0020 (15)
C12A0.080 (3)0.053 (3)0.103 (3)0.012 (2)0.032 (2)0.005 (2)
C13A0.070 (3)0.061 (3)0.085 (3)0.000 (2)0.0208 (19)0.0223 (19)
C19A0.043 (2)0.061 (3)0.0529 (19)0.0029 (17)0.0164 (15)0.0075 (16)
C18A0.063 (3)0.089 (3)0.070 (2)0.019 (2)0.026 (2)0.029 (2)
C17A0.058 (3)0.152 (5)0.067 (3)0.009 (3)0.015 (2)0.037 (3)
C16A0.062 (3)0.149 (5)0.056 (2)0.025 (3)0.0063 (19)0.002 (3)
C15A0.070 (3)0.093 (3)0.071 (3)0.024 (3)0.021 (2)0.016 (2)
C14A0.047 (2)0.057 (3)0.0547 (18)0.0068 (17)0.0169 (15)0.0019 (16)
C20A0.112 (4)0.042 (3)0.101 (3)0.010 (2)0.037 (3)0.0093 (19)
O1B0.112 (2)0.070 (2)0.097 (2)0.0028 (18)0.0041 (17)0.0178 (17)
O2B0.0601 (15)0.0579 (17)0.0451 (11)0.0045 (12)0.0104 (10)0.0001 (11)
N1B0.0416 (17)0.067 (2)0.0668 (17)0.0045 (15)0.0162 (13)0.0011 (15)
C1B0.064 (3)0.065 (3)0.086 (3)0.004 (2)0.010 (2)0.003 (2)
C2B0.0429 (19)0.059 (2)0.062 (2)0.0068 (16)0.0108 (16)0.0024 (18)
C3B0.045 (2)0.065 (3)0.0537 (19)0.0102 (17)0.0048 (14)0.0028 (17)
C4B0.0411 (18)0.059 (3)0.0471 (18)0.0066 (16)0.0066 (13)0.0007 (16)
C5B0.0369 (18)0.054 (2)0.0503 (19)0.0065 (15)0.0111 (13)0.0013 (16)
C6B0.049 (2)0.073 (3)0.0415 (17)0.0056 (18)0.0095 (14)0.0054 (17)
C7B0.048 (2)0.063 (3)0.063 (2)0.0059 (18)0.0141 (15)0.0152 (18)
C8B0.062 (2)0.073 (3)0.0413 (18)0.0052 (19)0.0014 (15)0.0024 (17)
C9B0.063 (2)0.063 (3)0.0520 (19)0.0001 (19)0.0011 (16)0.0091 (17)
C10B0.054 (2)0.053 (2)0.0444 (16)0.0045 (17)0.0123 (14)0.0052 (15)
C11B0.0466 (19)0.055 (2)0.0535 (17)0.0017 (16)0.0182 (13)0.0010 (15)
C12B0.055 (2)0.073 (3)0.076 (2)0.011 (2)0.0258 (17)0.0040 (19)
C13B0.092 (3)0.074 (3)0.058 (2)0.001 (2)0.0315 (19)0.0052 (18)
C14B0.048 (2)0.052 (2)0.0505 (18)0.0047 (17)0.0142 (15)0.0051 (15)
C15B0.055 (2)0.066 (3)0.065 (2)0.0009 (19)0.0120 (17)0.0038 (18)
C16B0.085 (3)0.058 (3)0.071 (2)0.007 (2)0.011 (2)0.0070 (19)
C17B0.108 (4)0.062 (3)0.060 (2)0.006 (2)0.018 (2)0.0111 (18)
C18B0.081 (3)0.063 (3)0.072 (2)0.017 (2)0.032 (2)0.002 (2)
C19B0.057 (2)0.051 (2)0.0518 (18)0.0075 (18)0.0184 (16)0.0048 (15)
C20B0.046 (2)0.107 (4)0.098 (3)0.002 (2)0.0237 (19)0.003 (2)
Geometric parameters (Å, º) top
O1A—C1A1.222 (4)O1B—C1B1.200 (5)
O2A—C5A1.376 (4)O2B—C5B1.365 (4)
O2A—C10A1.479 (4)O2B—C10B1.482 (4)
N1A—C19A1.392 (4)N1B—C19B1.406 (4)
N1A—C10A1.439 (4)N1B—C10B1.442 (4)
N1A—C20A1.453 (5)N1B—C20B1.450 (5)
C1A—C2A1.469 (5)C1B—C2B1.463 (5)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C7A1.384 (4)C2B—C7B1.395 (5)
C2A—C3A1.389 (5)C2B—C3B1.398 (5)
C3A—C4A1.380 (4)C3B—C4B1.376 (5)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.395 (4)C4B—C5B1.396 (4)
C4A—C8A1.453 (5)C4B—C8B1.448 (5)
C5A—C6A1.380 (4)C5B—C6B1.389 (5)
C6A—C7A1.380 (5)C6B—C7B1.378 (5)
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.321 (5)C8B—C9B1.319 (5)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.489 (4)C9B—C10B1.493 (5)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.562 (5)C10B—C11B1.561 (5)
C11A—C14A1.506 (5)C11B—C14B1.518 (5)
C11A—C12A1.527 (5)C11B—C12B1.531 (5)
C11A—C13A1.542 (5)C11B—C13B1.540 (5)
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C13A—H13A0.9600C13B—H13D0.9600
C13A—H13B0.9600C13B—H13E0.9600
C13A—H13C0.9600C13B—H13F0.9600
C19A—C14A1.382 (5)C14B—C15B1.374 (5)
C19A—C18A1.387 (5)C14B—C19B1.381 (5)
C18A—C17A1.363 (6)C15B—C16B1.387 (5)
C18A—H18A0.9300C15B—H15B0.9300
C17A—C16A1.363 (7)C16B—C17B1.365 (6)
C17A—H17A0.9300C16B—H16B0.9300
C16A—C15A1.405 (7)C17B—C18B1.378 (6)
C16A—H16A0.9300C17B—H17B0.9300
C15A—C14A1.383 (5)C18B—C19B1.391 (5)
C15A—H15A0.9300C18B—H18B0.9300
C20A—H20A0.9600C20B—H20D0.9600
C20A—H20B0.9600C20B—H20E0.9600
C20A—H20C0.9600C20B—H20F0.9600
C5A—O2A—C10A122.4 (2)C5B—O2B—C10B121.7 (2)
C19A—N1A—C10A108.5 (3)C19B—N1B—C10B108.3 (3)
C19A—N1A—C20A120.5 (3)C19B—N1B—C20B121.4 (3)
C10A—N1A—C20A119.6 (3)C10B—N1B—C20B120.1 (3)
O1A—C1A—C2A124.3 (4)O1B—C1B—C2B125.6 (4)
O1A—C1A—H1A117.8O1B—C1B—H1B117.2
C2A—C1A—H1A117.8C2B—C1B—H1B117.2
C7A—C2A—C3A119.1 (3)C7B—C2B—C3B118.4 (3)
C7A—C2A—C1A120.1 (3)C7B—C2B—C1B121.8 (3)
C3A—C2A—C1A120.9 (3)C3B—C2B—C1B119.8 (3)
C4A—C3A—C2A121.3 (3)C4B—C3B—C2B121.7 (3)
C4A—C3A—H3A119.3C4B—C3B—H3B119.2
C2A—C3A—H3A119.3C2B—C3B—H3B119.2
C3A—C4A—C5A118.3 (3)C3B—C4B—C5B118.4 (3)
C3A—C4A—C8A123.6 (3)C3B—C4B—C8B123.5 (3)
C5A—C4A—C8A118.1 (3)C5B—C4B—C8B118.0 (3)
O2A—C5A—C6A118.1 (3)O2B—C5B—C6B117.6 (3)
O2A—C5A—C4A120.8 (3)O2B—C5B—C4B121.2 (3)
C6A—C5A—C4A121.1 (3)C6B—C5B—C4B121.2 (3)
C7A—C6A—C5A119.4 (3)C7B—C6B—C5B119.2 (3)
C7A—C6A—H6A120.3C7B—C6B—H6B120.4
C5A—C6A—H6A120.3C5B—C6B—H6B120.4
C6A—C7A—C2A120.7 (3)C6B—C7B—C2B121.1 (3)
C6A—C7A—H7A119.7C6B—C7B—H7B119.5
C2A—C7A—H7A119.7C2B—C7B—H7B119.5
C9A—C8A—C4A120.9 (3)C9B—C8B—C4B120.9 (3)
C9A—C8A—H8A119.5C9B—C8B—H8B119.5
C4A—C8A—H8A119.5C4B—C8B—H8B119.5
C8A—C9A—C10A123.8 (3)C8B—C9B—C10B123.3 (3)
C8A—C9A—H9A118.1C8B—C9B—H9B118.4
C10A—C9A—H9A118.1C10B—C9B—H9B118.4
N1A—C10A—O2A105.9 (2)N1B—C10B—O2B105.6 (2)
N1A—C10A—C9A112.0 (3)N1B—C10B—C9B113.1 (3)
O2A—C10A—C9A110.9 (3)O2B—C10B—C9B110.8 (3)
N1A—C10A—C11A103.4 (3)N1B—C10B—C11B103.1 (3)
O2A—C10A—C11A107.8 (2)O2B—C10B—C11B108.6 (2)
C9A—C10A—C11A116.1 (3)C9B—C10B—C11B115.0 (3)
C14A—C11A—C12A115.4 (3)C14B—C11B—C12B114.3 (3)
C14A—C11A—C13A108.1 (3)C14B—C11B—C13B108.5 (3)
C12A—C11A—C13A109.5 (3)C12B—C11B—C13B109.6 (3)
C14A—C11A—C10A100.6 (3)C14B—C11B—C10B100.7 (2)
C12A—C11A—C10A112.1 (3)C12B—C11B—C10B112.3 (3)
C13A—C11A—C10A110.7 (3)C13B—C11B—C10B111.0 (3)
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C11A—C13A—H13A109.5C11B—C13B—H13D109.5
C11A—C13A—H13B109.5C11B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C11A—C13A—H13C109.5C11B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C14A—C19A—C18A122.0 (3)C15B—C14B—C19B120.2 (3)
C14A—C19A—N1A110.2 (3)C15B—C14B—C11B130.6 (3)
C18A—C19A—N1A127.7 (4)C19B—C14B—C11B109.1 (3)
C17A—C18A—C19A117.9 (4)C14B—C15B—C16B119.2 (4)
C17A—C18A—H18A121.1C14B—C15B—H15B120.4
C19A—C18A—H18A121.1C16B—C15B—H15B120.4
C18A—C17A—C16A121.9 (4)C17B—C16B—C15B120.3 (4)
C18A—C17A—H17A119.0C17B—C16B—H16B119.9
C16A—C17A—H17A119.0C15B—C16B—H16B119.9
C17A—C16A—C15A120.3 (4)C16B—C17B—C18B121.5 (3)
C17A—C16A—H16A119.9C16B—C17B—H17B119.2
C15A—C16A—H16A119.9C18B—C17B—H17B119.2
C14A—C15A—C16A118.8 (4)C17B—C18B—C19B118.0 (4)
C14A—C15A—H15A120.6C17B—C18B—H18B121.0
C16A—C15A—H15A120.6C19B—C18B—H18B121.0
C19A—C14A—C15A119.2 (4)C14B—C19B—C18B120.8 (3)
C19A—C14A—C11A109.0 (3)C14B—C19B—N1B109.7 (3)
C15A—C14A—C11A131.7 (4)C18B—C19B—N1B129.5 (3)
N1A—C20A—H20A109.5N1B—C20B—H20D109.5
N1A—C20A—H20B109.5N1B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
N1A—C20A—H20C109.5N1B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
O1A—C1A—C2A—C7A175.6 (4)O1B—C1B—C2B—C7B177.5 (4)
O1A—C1A—C2A—C3A3.0 (6)O1B—C1B—C2B—C3B1.2 (6)
C7A—C2A—C3A—C4A2.3 (5)C7B—C2B—C3B—C4B2.6 (5)
C1A—C2A—C3A—C4A176.3 (3)C1B—C2B—C3B—C4B176.1 (3)
C2A—C3A—C4A—C5A0.3 (5)C2B—C3B—C4B—C5B1.0 (5)
C2A—C3A—C4A—C8A179.5 (3)C2B—C3B—C4B—C8B179.1 (3)
C10A—O2A—C5A—C6A167.8 (3)C10B—O2B—C5B—C6B166.3 (3)
C10A—O2A—C5A—C4A13.7 (4)C10B—O2B—C5B—C4B14.3 (4)
C3A—C4A—C5A—O2A179.8 (3)C3B—C4B—C5B—O2B179.5 (3)
C8A—C4A—C5A—O2A1.0 (5)C8B—C4B—C5B—O2B2.3 (4)
C3A—C4A—C5A—C6A1.7 (5)C3B—C4B—C5B—C6B1.2 (5)
C8A—C4A—C5A—C6A177.5 (3)C8B—C4B—C5B—C6B177.0 (3)
O2A—C5A—C6A—C7A179.7 (3)O2B—C5B—C6B—C7B179.1 (3)
C4A—C5A—C6A—C7A1.7 (5)C4B—C5B—C6B—C7B1.6 (5)
C5A—C6A—C7A—C2A0.3 (5)C5B—C6B—C7B—C2B0.1 (5)
C3A—C2A—C7A—C6A2.2 (5)C3B—C2B—C7B—C6B2.1 (5)
C1A—C2A—C7A—C6A176.4 (3)C1B—C2B—C7B—C6B176.5 (3)
C3A—C4A—C8A—C9A174.3 (3)C3B—C4B—C8B—C9B174.4 (3)
C5A—C4A—C8A—C9A6.6 (5)C5B—C4B—C8B—C9B7.5 (5)
C4A—C8A—C9A—C10A2.5 (6)C4B—C8B—C9B—C10B4.0 (5)
C19A—N1A—C10A—O2A85.4 (3)C19B—N1B—C10B—O2B83.9 (3)
C20A—N1A—C10A—O2A58.2 (3)C20B—N1B—C10B—O2B61.8 (4)
C19A—N1A—C10A—C9A153.6 (3)C19B—N1B—C10B—C9B154.7 (3)
C20A—N1A—C10A—C9A62.8 (4)C20B—N1B—C10B—C9B59.5 (4)
C19A—N1A—C10A—C11A27.8 (3)C19B—N1B—C10B—C11B29.9 (3)
C20A—N1A—C10A—C11A171.4 (3)C20B—N1B—C10B—C11B175.7 (3)
C5A—O2A—C10A—N1A142.4 (3)C5B—O2B—C10B—N1B146.3 (3)
C5A—O2A—C10A—C9A20.7 (4)C5B—O2B—C10B—C9B23.4 (4)
C5A—O2A—C10A—C11A107.4 (3)C5B—O2B—C10B—C11B103.7 (3)
C8A—C9A—C10A—N1A133.3 (4)C8B—C9B—C10B—N1B136.8 (4)
C8A—C9A—C10A—O2A15.2 (5)C8B—C9B—C10B—O2B18.4 (5)
C8A—C9A—C10A—C11A108.2 (4)C8B—C9B—C10B—C11B105.1 (4)
N1A—C10A—C11A—C14A26.7 (3)N1B—C10B—C11B—C14B27.7 (3)
O2A—C10A—C11A—C14A85.2 (3)O2B—C10B—C11B—C14B84.0 (3)
C9A—C10A—C11A—C14A149.8 (3)C9B—C10B—C11B—C14B151.3 (3)
N1A—C10A—C11A—C12A149.9 (3)N1B—C10B—C11B—C12B149.8 (3)
O2A—C10A—C11A—C12A38.1 (4)O2B—C10B—C11B—C12B38.1 (3)
C9A—C10A—C11A—C12A87.0 (4)C9B—C10B—C11B—C12B86.6 (4)
N1A—C10A—C11A—C13A87.4 (3)N1B—C10B—C11B—C13B87.0 (3)
O2A—C10A—C11A—C13A160.7 (3)O2B—C10B—C11B—C13B161.3 (3)
C9A—C10A—C11A—C13A35.6 (4)C9B—C10B—C11B—C13B36.5 (4)
C10A—N1A—C19A—C14A17.6 (3)C12B—C11B—C14B—C15B45.6 (5)
C20A—N1A—C19A—C14A160.8 (3)C13B—C11B—C14B—C15B77.1 (4)
C10A—N1A—C19A—C18A164.9 (3)C10B—C11B—C14B—C15B166.3 (3)
C20A—N1A—C19A—C18A21.7 (5)C12B—C11B—C14B—C19B137.8 (3)
C14A—C19A—C18A—C17A0.2 (5)C13B—C11B—C14B—C19B99.5 (3)
N1A—C19A—C18A—C17A177.4 (3)C10B—C11B—C14B—C19B17.1 (3)
C19A—C18A—C17A—C16A1.0 (6)C19B—C14B—C15B—C16B1.8 (5)
C18A—C17A—C16A—C15A1.8 (7)C11B—C14B—C15B—C16B178.1 (3)
C17A—C16A—C15A—C14A1.4 (6)C14B—C15B—C16B—C17B0.2 (5)
C18A—C19A—C14A—C15A0.4 (5)C15B—C16B—C17B—C18B1.3 (6)
N1A—C19A—C14A—C15A178.1 (3)C16B—C17B—C18B—C19B1.2 (6)
C18A—C19A—C14A—C11A176.4 (3)C15B—C14B—C19B—C18B2.0 (5)
N1A—C19A—C14A—C11A1.3 (3)C11B—C14B—C19B—C18B179.0 (3)
C16A—C15A—C14A—C19A0.3 (5)C15B—C14B—C19B—N1B176.5 (3)
C16A—C15A—C14A—C11A176.3 (3)C11B—C14B—C19B—N1B0.5 (4)
C12A—C11A—C14A—C19A138.4 (3)C17B—C18B—C19B—C14B0.4 (5)
C13A—C11A—C14A—C19A98.6 (3)C17B—C18B—C19B—N1B177.7 (3)
C10A—C11A—C14A—C19A17.5 (3)C10B—N1B—C19B—C14B20.0 (3)
C12A—C11A—C14A—C15A45.3 (5)C20B—N1B—C19B—C14B165.3 (3)
C13A—C11A—C14A—C15A77.7 (4)C10B—N1B—C19B—C18B161.7 (3)
C10A—C11A—C14A—C15A166.2 (3)C20B—N1B—C19B—C18B16.4 (5)

Experimental details

(I_C2c)(I_Cc)
Crystal data
Chemical formulaC20H19NO2C20H19NO2
Mr305.36305.36
Crystal system, space groupMonoclinic, C2/cMonoclinic, Cc
Temperature (K)293293
a, b, c (Å)21.447 (4), 11.226 (2), 28.221 (6)11.699 (2), 11.692 (2), 24.406 (5)
β (°) 103.57 (2) 102.13 (3)
V3)6605 (2)3263.8 (10)
Z168
Radiation typeMo KαMo Kα
µ (mm1)0.080.08
Crystal size (mm)0.05 × 0.04 × 0.020.04 × 0.03 × 0.03
Data collection
DiffractometerNonius Kappa CCD
diffractometer
Nonius Kappa CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15238, 7218, 3291 12585, 5001, 3405
Rint0.0710.050
(sin θ/λ)max1)0.6400.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.169, 0.89 0.036, 0.091, 0.95
No. of reflections72182878
No. of parameters421422
No. of restraints02
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.200.12, 0.13

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008) and maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), Please give details.

Comparison of relevant torsion angles and angles between planes in the crystal structures of the dimorphs top
Angle (°)C2/cCc
ABAB
C9-C10-O2-O58.2 (3)-12.7 (3)-20.7 (4)-23.1 (4)
C10-O2-C5-C4-3.5 (3)8.8 (3)13.6 (5)14.3 (4)
O2-C5-C4-C8-2.3 (3)-0.2 (3)1.0 (5)2.3 (5)
C5-C4-C8-C92.5 (4)-4.0 (4)-6.6 (5)-7.5 (5)
C4-C8-C9-C103.1 (4)-1.2 (4)-2.6 (6)-4.1 (6)
C8-C9-C10-O2-8.1 (4)8.9 (4)15.3 (5)18.4 (5)
C3-C2-C1-O1-177.2 (3)-4.8 (4)-3.0 (6)-1.2 (6)
α89.7 (1)87.3 (1)89.6 (2)89.3 (2)
β26.5 (1)23.0 (1)26.4 (3)28.2 (3)
γ6.8 (3)-10.5 (1)17.2 (1)20.0 (2)
Comparison of short intermolecular distances in the crystal structures of the dimorphs top
Atom 1Atom 2distance (Å)Symmetry 2
Dimorph in C2/c
C3AH12F2.8871/2-x, -1/2+y, 1/2-z
Dimorph in Cc
C7AH12B2.8751/2+x, -1/2+y, z
C1AC20A3.3721/2+x, 1/2+y, z
C2AC20A3.3001/2+x, 1/2+y, z
C2AH20C2.8801/2+x, 1/2+y, z
O1AH16B2.6851+x, -y, 1/2+z
C7BC20B3.319-1/2+x, 1/2+y, z
C7BH20F2.863-1/2+x, 1/2+y, z
C2BH12F2.8081/2+x, 1/2+y, z
 

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