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The title compound, C24H22N2O3, is dimerized via two intermolecular O—H...O hydrogen bonds contributed by two —COOH groups, resulting in the formation of a planar eight-membered ring. The spiro C atom links two planes that are almost perpendicular to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023632/tk6087sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023632/tk6087Isup2.hkl
Contains datablock I

CCDC reference: 204680

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.123
  • Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Spiro-oxazines are novel organic photochromic compounds that are attractive as functional materials for a wide variety of applications, including high-density optical storage devices, optical switches and non-linear optics (Swansburg et al., 2000). Recently, the title compound, (I), was found to exhibit interesting photochemical properties when applied to DNA modifications (Zhang et al., 2001). Thus, the elucidation of the crystal structure of (I) is of importance. To our knowledge, this is the first reported crystal structure determination of dimerized photochromic spiro compound via intermolecular O—H···O hydrogen bonds. The spiro-center C12 in (I) (Fig. 1 and Table 1) is tetrahedral, as expected, with the dihedral angle between the planes O1—C12—C11 and N2—C12—C13 being 89.71 (13)°. The five-membered indoline ring (C12—C13—C14—C19—N2) is non-planar, adopting an flattened envelope conformation. Atom C12 lies 0.4763 (31) Å out of the plane of the other four indoline ring atoms; the torsion angle C13—C14—C19—N2 is −1.5 (3)° and the bending angle along the N2···C13 line is 30.59 (12)°. The N2, C13 and phenyl ring atoms are close to being coplanar [the interplanar angle between the phenyl ring and the plane through C13—C14—C19—N2 is only 1.82 (13)°]. Atom N2 has a pyramidal configuration and lies out of the plane of adjacent atoms by 0.2451 (21) Å with the sum of the bond angles at N2 being 351.30 (52)°. As found for the indoline ring, the oxazine moiety also has an envelope conformation, with C12 0.3335 (31) Å from the plane of the other oxazine atoms. The naphthyl ring, along with N1, C11 and O1, constitutes a roughly planar shape with a maximum deviation of 0.084 (18) Å at C11; the dihedral angle between this plane and C11—C12—O1 is 23.83 (14)°, indicating that spiro-atom C12 lies out of the naphthyl ring.

The main feature of the crystal structure, compared to the report of Osano et al. (1991), is the dimerization in the crystalline state (Fig. 1), which occurs when two molecules approach in a head-to-head fashion with the formation of a centrosymmetric eight-membered ring via hydrogen bonding. The O2···O3i separation is 2.632 (3) Å and the H2···O3i distance is 1.78 Å with an angle of 178°, subtended at H [symmetry code: (i) 2 − x, −y, −z].

Experimental top

The title compound was synthesized as described by Li et al. (1999). The single-crystal was grown by slow evaporation of chloroform–ethanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of dimerized (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
3-[3,3-Dimethylspiro[2,3-dihydro-1H-indole-2,3'-(3'H-naphtho[2,1-b] [1,4]oxazine)]-1-yl]propionic acid top
Crystal data top
C24H22N2O3F(000) = 816
Mr = 386.44Dx = 1.328 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 912 reflections
a = 13.373 (5) Åθ = 3.2–23.4°
b = 11.527 (4) ŵ = 0.09 mm1
c = 13.485 (5) ÅT = 293 K
β = 111.538 (6)°Plate, pale_yellow
V = 1933.5 (11) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3399 independent reflections
Radiation source: fine-focus sealed tube2000 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1514
Tmin = 0.983, Tmax = 1k = 138
7838 measured reflectionsl = 1416
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0562P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3399 reflectionsΔρmax = 0.16 e Å3
263 parametersΔρmin = 0.18 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0055 (11)
Crystal data top
C24H22N2O3V = 1933.5 (11) Å3
Mr = 386.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.373 (5) ŵ = 0.09 mm1
b = 11.527 (4) ÅT = 293 K
c = 13.485 (5) Å0.20 × 0.15 × 0.10 mm
β = 111.538 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3399 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2000 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 1Rint = 0.047
7838 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.123H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
3399 reflectionsΔρmin = 0.18 e Å3
263 parameters
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
O10.80725 (12)0.00877 (12)0.12839 (11)0.0430 (4)
N20.84053 (15)0.17499 (14)0.23458 (13)0.0395 (5)
C110.72245 (19)0.18821 (19)0.04688 (18)0.0437 (6)
H11A0.71490.26740.05510.052*
O21.05049 (14)0.03606 (15)0.14008 (14)0.0632 (5)
H21.04310.06260.07900.095*
O30.97452 (14)0.12205 (14)0.04836 (14)0.0568 (5)
C10.71755 (18)0.03272 (19)0.05998 (18)0.0386 (6)
C20.68406 (18)0.0158 (2)0.16406 (18)0.0404 (6)
C30.63130 (19)0.0496 (2)0.25736 (19)0.0495 (6)
H3A0.61850.12810.25170.059*
C40.5990 (2)0.0006 (3)0.3552 (2)0.0635 (8)
H4A0.56440.04390.41570.076*
C50.6174 (2)0.1187 (3)0.3659 (2)0.0705 (9)
H5A0.59380.15260.43310.085*
C60.6694 (2)0.1837 (2)0.2785 (2)0.0596 (7)
H6A0.68180.26190.28630.072*
C70.70496 (19)0.1343 (2)0.17560 (19)0.0461 (6)
C80.7620 (2)0.1993 (2)0.0833 (2)0.0532 (7)
H8A0.77690.27700.09040.064*
C90.7958 (2)0.1513 (2)0.0158 (2)0.0504 (7)
H9A0.83470.19510.07550.061*
C100.77120 (18)0.03513 (19)0.02675 (18)0.0394 (6)
N10.69979 (15)0.15171 (16)0.04820 (14)0.0437 (5)
C120.76019 (17)0.11648 (18)0.14733 (16)0.0381 (6)
C130.67162 (18)0.08711 (19)0.19386 (18)0.0428 (6)
C140.73999 (19)0.07577 (18)0.31076 (17)0.0400 (6)
C150.7180 (2)0.0261 (2)0.39361 (19)0.0502 (7)
H15A0.65250.01040.38120.060*
C160.7956 (2)0.0315 (2)0.4962 (2)0.0552 (7)
H16A0.78260.00310.55270.066*
C170.8908 (2)0.0875 (2)0.5141 (2)0.0545 (7)
H17A0.94120.09210.58330.065*
C180.91385 (19)0.1378 (2)0.43153 (18)0.0468 (6)
H18A0.97900.17520.44430.056*
C190.83749 (18)0.13055 (18)0.33018 (17)0.0384 (6)
C200.94125 (18)0.21569 (19)0.22868 (18)0.0451 (6)
H20A0.97290.27150.28550.054*
H20B0.92520.25630.16160.054*
C211.02480 (19)0.1224 (2)0.23696 (18)0.0505 (7)
H21A1.09590.15630.26850.061*
H21B1.01900.06180.28450.061*
C221.01360 (19)0.0692 (2)0.1328 (2)0.0475 (6)
C230.5937 (2)0.1893 (2)0.1783 (2)0.0639 (8)
H23A0.54020.16960.20730.096*
H23B0.55940.20570.10370.096*
H23C0.63280.25640.21440.096*
C240.6085 (2)0.0223 (2)0.1449 (2)0.0616 (8)
H24A0.55500.03620.17540.092*
H24B0.65660.08730.15940.092*
H24C0.57410.01230.06930.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0492 (10)0.0396 (10)0.0398 (10)0.0039 (7)0.0159 (8)0.0005 (7)
N20.0388 (12)0.0451 (12)0.0368 (11)0.0063 (9)0.0166 (9)0.0036 (9)
C110.0502 (16)0.0344 (14)0.0479 (15)0.0029 (11)0.0195 (12)0.0002 (11)
O20.0732 (13)0.0569 (12)0.0658 (12)0.0227 (10)0.0331 (10)0.0055 (9)
O30.0727 (13)0.0523 (11)0.0574 (11)0.0136 (9)0.0380 (10)0.0091 (9)
C10.0404 (14)0.0349 (14)0.0427 (14)0.0019 (10)0.0177 (11)0.0022 (11)
C20.0333 (13)0.0465 (15)0.0459 (15)0.0067 (11)0.0197 (11)0.0053 (11)
C30.0444 (15)0.0600 (17)0.0453 (16)0.0033 (12)0.0179 (12)0.0050 (12)
C40.0548 (18)0.088 (2)0.0429 (16)0.0046 (15)0.0129 (13)0.0085 (14)
C50.063 (2)0.089 (2)0.056 (2)0.0054 (17)0.0182 (16)0.0272 (17)
C60.0581 (18)0.0563 (18)0.067 (2)0.0092 (13)0.0263 (15)0.0232 (15)
C70.0435 (15)0.0476 (16)0.0516 (16)0.0091 (12)0.0228 (12)0.0101 (12)
C80.0631 (18)0.0368 (15)0.0701 (19)0.0052 (12)0.0366 (15)0.0085 (13)
C90.0594 (17)0.0401 (15)0.0579 (17)0.0041 (12)0.0288 (14)0.0034 (12)
C100.0400 (14)0.0372 (14)0.0451 (15)0.0034 (11)0.0204 (11)0.0026 (11)
N10.0517 (13)0.0422 (12)0.0393 (12)0.0017 (9)0.0190 (9)0.0009 (9)
C120.0403 (14)0.0351 (13)0.0397 (14)0.0035 (10)0.0155 (11)0.0007 (10)
C130.0362 (14)0.0471 (15)0.0456 (15)0.0003 (11)0.0154 (11)0.0046 (11)
C140.0417 (14)0.0405 (14)0.0411 (14)0.0020 (11)0.0189 (11)0.0032 (11)
C150.0501 (16)0.0496 (16)0.0580 (17)0.0015 (12)0.0280 (14)0.0057 (12)
C160.071 (2)0.0566 (17)0.0468 (17)0.0101 (14)0.0313 (15)0.0116 (12)
C170.0608 (19)0.0597 (17)0.0405 (15)0.0103 (14)0.0158 (13)0.0034 (12)
C180.0439 (15)0.0485 (15)0.0470 (16)0.0000 (12)0.0156 (12)0.0051 (12)
C190.0403 (14)0.0395 (14)0.0376 (14)0.0039 (11)0.0169 (11)0.0008 (10)
C200.0469 (16)0.0430 (15)0.0511 (15)0.0050 (12)0.0247 (12)0.0053 (11)
C210.0458 (15)0.0535 (16)0.0559 (17)0.0037 (12)0.0231 (12)0.0016 (12)
C220.0409 (15)0.0519 (17)0.0582 (18)0.0065 (12)0.0283 (12)0.0069 (13)
C230.0509 (18)0.081 (2)0.0617 (18)0.0177 (14)0.0233 (14)0.0174 (14)
C240.0470 (16)0.076 (2)0.0602 (18)0.0186 (14)0.0175 (13)0.0005 (14)
Geometric parameters (Å, º) top
O1—C101.372 (2)C9—H9A0.9300
O1—C121.456 (2)C12—C131.567 (3)
N2—C191.402 (3)C13—C141.510 (3)
N2—C121.437 (3)C13—C241.527 (3)
N2—C201.456 (3)C13—C231.535 (3)
C11—N11.276 (3)C14—C151.380 (3)
C11—C121.507 (3)C14—C191.384 (3)
C11—H11A0.9300C15—C161.393 (3)
O2—C221.300 (3)C15—H15A0.9300
O2—H20.8501C16—C171.367 (4)
O3—C221.226 (3)C16—H16A0.9300
C1—C101.370 (3)C17—C181.387 (3)
C1—N11.411 (3)C17—H17A0.9300
C1—C21.422 (3)C18—C191.376 (3)
C2—C31.413 (3)C18—H18A0.9300
C2—C71.414 (3)C20—C211.525 (3)
C3—C41.358 (3)C20—H20A0.9700
C3—H3A0.9300C20—H20B0.9700
C4—C51.400 (4)C21—C221.489 (3)
C4—H4A0.9300C21—H21A0.9700
C5—C61.353 (4)C21—H21B0.9700
C5—H5A0.9300C23—H23A0.9600
C6—C71.411 (3)C23—H23B0.9600
C6—H6A0.9300C23—H23C0.9600
C7—C81.413 (3)C24—H24A0.9600
C8—C91.361 (3)C24—H24B0.9600
C8—H8A0.9300C24—H24C0.9600
C9—C101.399 (3)
C10—O1—C12118.28 (16)C14—C13—C12100.35 (17)
C19—N2—C12108.43 (17)C24—C13—C12112.63 (19)
C19—N2—C20120.52 (18)C23—C13—C12110.77 (19)
C12—N2—C20122.35 (17)C15—C14—C19120.1 (2)
N1—C11—C12126.9 (2)C15—C14—C13130.9 (2)
N1—C11—H11A116.6C19—C14—C13108.98 (19)
C12—C11—H11A116.6C14—C15—C16118.9 (2)
C22—O2—H2110.9C14—C15—H15A120.5
C10—C1—N1121.05 (19)C16—C15—H15A120.5
C10—C1—C2119.6 (2)C17—C16—C15120.1 (2)
N1—C1—C2119.3 (2)C17—C16—H16A119.9
C3—C2—C7118.1 (2)C15—C16—H16A119.9
C3—C2—C1122.8 (2)C16—C17—C18121.5 (2)
C7—C2—C1119.0 (2)C16—C17—H17A119.2
C4—C3—C2121.0 (2)C18—C17—H17A119.2
C4—C3—H3A119.5C19—C18—C17118.0 (2)
C2—C3—H3A119.5C19—C18—H18A121.0
C3—C4—C5120.6 (3)C17—C18—H18A121.0
C3—C4—H4A119.7C18—C19—C14121.3 (2)
C5—C4—H4A119.7C18—C19—N2129.1 (2)
C6—C5—C4120.2 (3)C14—C19—N2109.64 (19)
C6—C5—H5A119.9N2—C20—C21115.88 (19)
C4—C5—H5A119.9N2—C20—H20A108.3
C5—C6—C7120.8 (3)C21—C20—H20A108.3
C5—C6—H6A119.6N2—C20—H20B108.3
C7—C6—H6A119.6C21—C20—H20B108.3
C6—C7—C8122.1 (2)H20A—C20—H20B107.4
C6—C7—C2119.3 (2)C22—C21—C20113.8 (2)
C8—C7—C2118.7 (2)C22—C21—H21A108.8
C9—C8—C7121.8 (2)C20—C21—H21A108.8
C9—C8—H8A119.1C22—C21—H21B108.8
C7—C8—H8A119.1C20—C21—H21B108.8
C8—C9—C10119.1 (2)H21A—C21—H21B107.7
C8—C9—H9A120.5O3—C22—O2123.7 (2)
C10—C9—H9A120.5O3—C22—C21122.2 (2)
C1—C10—O1121.6 (2)O2—C22—C21114.2 (2)
C1—C10—C9121.7 (2)C13—C23—H23A109.5
O1—C10—C9116.6 (2)C13—C23—H23B109.5
C11—N1—C1116.49 (19)H23A—C23—H23B109.5
N2—C12—O1107.60 (16)C13—C23—H23C109.5
N2—C12—C11112.42 (18)H23A—C23—H23C109.5
O1—C12—C11109.50 (17)H23B—C23—H23C109.5
N2—C12—C13102.79 (17)C13—C24—H24A109.5
O1—C12—C13108.95 (17)C13—C24—H24B109.5
C11—C12—C13115.17 (18)H24A—C24—H24B109.5
C14—C13—C24113.99 (19)C13—C24—H24C109.5
C14—C13—C23109.22 (19)H24A—C24—H24C109.5
C24—C13—C23109.6 (2)H24B—C24—H24C109.5
C10—C1—C2—C3178.0 (2)N1—C11—C12—N2141.5 (2)
N1—C1—C2—C31.3 (3)N1—C11—C12—O122.0 (3)
C10—C1—C2—C71.4 (3)N1—C11—C12—C13101.2 (3)
N1—C1—C2—C7178.10 (19)N2—C12—C13—C1429.1 (2)
C7—C2—C3—C41.7 (3)O1—C12—C13—C1484.81 (19)
C1—C2—C3—C4178.9 (2)C11—C12—C13—C14151.73 (18)
C2—C3—C4—C50.0 (4)N2—C12—C13—C24150.73 (18)
C3—C4—C5—C61.2 (4)O1—C12—C13—C2436.8 (2)
C4—C5—C6—C70.6 (4)C11—C12—C13—C2486.7 (2)
C5—C6—C7—C8178.2 (2)N2—C12—C13—C2386.2 (2)
C5—C6—C7—C21.2 (4)O1—C12—C13—C23159.89 (18)
C3—C2—C7—C62.3 (3)C11—C12—C13—C2336.4 (3)
C1—C2—C7—C6178.3 (2)C24—C13—C14—C1542.8 (3)
C3—C2—C7—C8177.1 (2)C23—C13—C14—C1580.1 (3)
C1—C2—C7—C82.3 (3)C12—C13—C14—C15163.4 (2)
C6—C7—C8—C9179.8 (2)C24—C13—C14—C19139.8 (2)
C2—C7—C8—C90.9 (3)C23—C13—C14—C1997.3 (2)
C7—C8—C9—C101.5 (4)C12—C13—C14—C1919.1 (2)
N1—C1—C10—O11.7 (3)C19—C14—C15—C160.4 (3)
C2—C1—C10—O1178.4 (2)C13—C14—C15—C16177.6 (2)
N1—C1—C10—C9175.6 (2)C14—C15—C16—C171.4 (4)
C2—C1—C10—C91.1 (3)C15—C16—C17—C181.5 (4)
C12—O1—C10—C118.9 (3)C16—C17—C18—C190.5 (4)
C12—O1—C10—C9163.61 (19)C17—C18—C19—C140.5 (3)
C8—C9—C10—C12.5 (4)C17—C18—C19—N2179.0 (2)
C8—C9—C10—O1180.0 (2)C15—C14—C19—C180.6 (3)
C12—C11—N1—C13.7 (3)C13—C14—C19—C18177.22 (19)
C10—C1—N1—C119.5 (3)C15—C14—C19—N2179.3 (2)
C2—C1—N1—C11173.8 (2)C13—C14—C19—N21.5 (3)
C19—N2—C12—O184.6 (2)C12—N2—C19—C18162.2 (2)
C20—N2—C12—O163.1 (2)C20—N2—C19—C1813.9 (3)
C19—N2—C12—C11154.78 (18)C12—N2—C19—C1419.1 (2)
C20—N2—C12—C1157.6 (3)C20—N2—C19—C14167.47 (19)
C19—N2—C12—C1330.3 (2)C19—N2—C20—C2168.9 (3)
C20—N2—C12—C13177.99 (18)C12—N2—C20—C2175.0 (3)
C10—O1—C12—N2150.52 (18)N2—C20—C21—C2287.8 (3)
C10—O1—C12—C1128.1 (2)C20—C21—C22—O327.9 (3)
C10—O1—C12—C1398.7 (2)C20—C21—C22—O2153.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.851.782.632 (3)178
Symmetry code: (i) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC24H22N2O3
Mr386.44
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)13.373 (5), 11.527 (4), 13.485 (5)
β (°) 111.538 (6)
V3)1933.5 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.983, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
7838, 3399, 2000
Rint0.047
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.123, 1.02
No. of reflections3399
No. of parameters263
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C121.456 (2)C11—N11.276 (3)
N2—C191.402 (3)C11—C121.507 (3)
N2—C121.437 (3)O2—H20.8501
N2—C201.456 (3)C12—C131.567 (3)
C10—O1—C12118.28 (16)O1—C12—C11109.50 (17)
C19—N2—C12108.43 (17)N2—C12—C13102.79 (17)
C19—N2—C20120.52 (18)O1—C12—C13108.95 (17)
C12—N2—C20122.35 (17)C11—C12—C13115.17 (18)
N1—C11—C12126.9 (2)C14—C13—C12100.35 (17)
C22—O2—H2110.9C19—C14—C13108.98 (19)
C10—C1—N1121.05 (19)C14—C19—N2109.64 (19)
C1—C10—O1121.6 (2)O3—C22—O2123.7 (2)
C11—N1—C1116.49 (19)O3—C22—C21122.2 (2)
N2—C12—O1107.60 (16)O2—C22—C21114.2 (2)
N2—C12—C11112.42 (18)
N1—C1—C10—O11.7 (3)N1—C11—C12—N2141.5 (2)
C2—C1—C10—O1178.4 (2)N1—C11—C12—O122.0 (3)
N1—C1—C10—C9175.6 (2)N1—C11—C12—C13101.2 (3)
C12—O1—C10—C118.9 (3)N2—C12—C13—C1429.1 (2)
C12—O1—C10—C9163.61 (19)O1—C12—C13—C1484.81 (19)
C12—C11—N1—C13.7 (3)C11—C12—C13—C14151.73 (18)
C10—C1—N1—C119.5 (3)C12—C13—C14—C1919.1 (2)
C19—N2—C12—O184.6 (2)C13—C14—C19—C18177.22 (19)
C19—N2—C12—C11154.78 (18)C15—C14—C19—N2179.3 (2)
C19—N2—C12—C1330.3 (2)C13—C14—C19—N21.5 (3)
C10—O1—C12—N2150.52 (18)C12—N2—C19—C18162.2 (2)
C10—O1—C12—C1128.1 (2)C12—N2—C19—C1419.1 (2)
C10—O1—C12—C1398.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.851.782.632 (3)178
Symmetry code: (i) x+2, y, z.
 

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