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In 4,4′-biphenol–1,10-phenanthroline (1/1) [systematic name: 4,4′-biphenyldiol–1,10-phenanthroline (1/1)] the diphenol molecules lie across centres of inversion and the phenanthroline molecules lie across twofold rotation axes; the phenanthroline molecules act as chain-building units and the molecular components are linked into steeply zigzag C(16) chains parallel to [101] by means of O—H...N hydrogen bonds. In the structure of ­4,4′-­thiodiphenol–1,10-phenanthroline (1/2) the phenanthroline molecules act as chain-terminating units; the supramolecular aggregation is finite, with the bisphenol linked to each phenanthroline molecule by means of a single O—H...N hydrogen bond. π−π stacking interactions between the phenanthroline molecules in neighbouring hydrogen-bonded aggregates serve to link these aggregates into a continuous two-dimensional array. The phenanthroline molecules in 4,4′-sulfonyldiphenol–1,10-phenanthroline (2/3) play two roles: ­molecules in general positions act as chain-terminating units and are linked to the sulfonyldiphenol molecules by means of three-centre O—H...(N)2 hydrogen bonds, while those lying across twofold rotation axes act as chain builders and are linked to two different sulfonyldiphenol molecules by means of a two-centre O—H...N hydrogen bond in each case; the resulting U-shaped five-­component aggregates are further linked by C—H...O=S hydrogen bonds into a C_3^3(17)[R_2^2(12)] `chain of rings' along [001]. In 1,1,1-­tris(4-hydroxyphenyl)ethane–1,10-phenanthroline–methanol (1/1/1) [systematic name: 4,4′,4′′-ethylidynetriphenol–1,10-phenanthroline–methanol (1/1/1)] the phenanthroline molecules again act as chain-terminating units: the trisphenol molecules and the methanol molecules are linked by O—H...O hydrogen bonds into two-dimensional nets built from R_6^6(42) rings, and pairs of these nets are interwoven. The formation of each net utilizes two hydroxyl groups per trisphenol molecule as hydrogen-bond donors and the remaining hydroxyl group acts as donor to the phenanthroline molecule in a three-centre O—H...(N)2 hydrogenbond.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, 1, 2, 3, 4

hkl

Structure factor file (CIF format)
Contains datablock 1

hkl

Structure factor file (CIF format)
Contains datablock 2

hkl

Structure factor file (CIF format)
Contains datablock 3

hkl

Structure factor file (CIF format)
Contains datablock 4

CCDC references: 134767; 134768; 134769; 134770

Computing details top

For all compounds, data collection: CAD4 (Enraf-Nonius, 1992); cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (1), (3), (4); DATRD2 in NRCVAX96 (Gabe et al., 1989 1989) for (2). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(1) 4,4'-Biphenol–1,10-phenanthroline (1/1) top
Crystal data top
C12H10O2·C12H8N2? #Insert any comments here.
Mr = 366.40Dx = 1.315 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
a = 13.0288 (17) ÅCell parameters from 25 reflections
b = 12.1865 (10) Åθ = 9.8–18.8°
c = 12.0778 (12) ŵ = 0.09 mm1
β = 105.199 (9)°T = 294 K
V = 1850.6 (3) Å3Lath, colorless
Z = 40.42 × 0.31 × 0.12 mm
F(000) = 768
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.012
Radiation source: X-ray tubeθmax = 25.2°, θmin = 2.3°
Graphite monochromatorh = 1515
θ/2θ scansk = 014
1748 measured reflectionsl = 014
1678 independent reflections3 standard reflections every 120 min
915 reflections with I > 2σ(I) intensity decay: no decay, variation 0.5%
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)] = 0.033H-atom parameters constrained
wR(F2) = 0.099Calculated w = 1/[σ2(Fo2) + (0.0542P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
1678 reflectionsΔρmax = 0.14 e Å3
129 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (9)
Crystal data top
C12H10O2·C12H8N2V = 1850.6 (3) Å3
Mr = 366.40Z = 4
Monoclinic, C2/cMo Kα radiation
a = 13.0288 (17) ŵ = 0.09 mm1
b = 12.1865 (10) ÅT = 294 K
c = 12.0778 (12) Å0.42 × 0.31 × 0.12 mm
β = 105.199 (9)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.012
1748 measured reflections3 standard reflections every 120 min
1678 independent reflections intensity decay: no decay, variation 0.5%
915 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 0.98Δρmax = 0.14 e Å3
1678 reflectionsΔρmin = 0.13 e Å3
129 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean plane data from last SHELXL run

The site labelled as "INV" is the inversion centre at (1/4, 0.25 0.0) and the -0.0846 (14) Å displacement of this site from the mean plane of the phenolic ring shows that the two rings are "stepped" slightly (by 0.169 Å).

Equivalent positions are: $1 1-X, Y, 0.5-Z $2 0.5-X, 0.5-Y, –Z

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.4764 (0.0079) x - 6.6901 (0.0053) y + 4.0560 (0.0079) z = 0.5312 (0.0037)

* -0.0391 (0.0013) C11 * -0.0055 (0.0013) C12 * 0.0397 (0.0014) C13 * 0.0111 (0.0014) C14 * 0.0292 (0.0014) C15 * 0.0072 (0.0012) C16 * -0.0426 (0.0010) O14 - 0.1301 (0.0028) C11_$2 - 0.1637 (0.0032) C12_$2 - 0.2089 (0.0030) C13_$2 - 0.1803 (0.0029) C14_$2 - 0.1984 (0.0031) C15_$2 - 0.1764 (0.0031) C16_$2 - 0.1266 (0.0030) O14_$2 - 0.0846 (0.0014) INV

Rms deviation of fitted atoms = 0.0292

8.4764 (0.0079) x - 6.6901 (0.0053) y + 4.0560 (0.0079) z = 0.3620 (0.0028)

Angle to previous plane (with approximate e.s.d.) = 0.00 (0.12)

* 0.0391 (0.0013) C11_$2 * 0.0055 (0.0013) C12_$2 * -0.0397 (0.0014) C13_$2 * -0.0111 (0.0014) C14_$2 * -0.0292 (0.0014) C15_$2 * -0.0072 (0.0012) C16_$2 * 0.0426 (0.0010) O14_$2 0.1301 (0.0028) C11 0.1637 (0.0032) C12 0.2089 (0.0030) C13 0.1803 (0.0029) C14 0.1984 (0.0031) C15 0.1764 (0.0031) C16 0.1266 (0.0030) O14 0.0846 (0.0014) INV

Rms deviation of fitted atoms = 0.0292

12.5950 (0.0033) x - 0.0470 (0.0093) y - 6.0432 (0.0082) z = 4.7223 (0.0082)

Angle to previous plane (with approximate e.s.d.) = 60.21 (0.05)

* -0.0118 (0.0012) N1 * 0.0116 (0.0012) C2 * -0.0007 (0.0012) C3 * -0.0102 (0.0014) C4 * 0.0100 (0.0015) C5 * 0.0010 (0.0014) C6 - 0.0015 (0.0031) C7 0.0707 (0.0037) N1_$1 0.0381 (0.0034) C2_$1 0.0409 (0.0041) C3_$1 0.0506 (0.0043) C4_$1 0.0396 (0.0034) C5_$1 0.0576 (0.0041) C6_$1 0.0323 (0.0036) C7_$1

Rms deviation of fitted atoms = 0.0089

12.5950 (0.0033) x + 0.0470 (0.0093) y - 6.0432 (0.0082) z = 4.8511 (0.0089)

Angle to previous plane (with approximate e.s.d.) = 0.44 (0.05)

* 0.0118 (0.0012) N1_$1 * -0.0117 (0.0012) C2_$1 * 0.0007 (0.0012) C3_$1 * 0.0102 (0.0014) C4_$1 * -0.0100 (0.0015) C5_$1 * -0.0010 (0.0014) C6_$1 0.0015 (0.0031) C7_$1 - 0.0323 (0.0036) C7 - 0.0707 (0.0037) N1 - 0.0381 (0.0034) C2 - 0.0409 (0.0041) C3 - 0.0506 (0.0043) C4 - 0.0396 (0.0034) C5 - 0.0576 (0.0041) C6

Rms deviation of fitted atoms = 0.0089

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.44259 (12)0.74375 (12)0.13717 (12)0.0563 (4)
C20.47035 (13)0.84112 (14)0.19040 (14)0.0481 (4)
C30.44280 (14)0.94214 (16)0.13423 (16)0.0568 (5)
C40.38652 (16)0.9395 (2)0.01853 (19)0.0703 (6)
C50.36177 (17)0.8425 (2)0.03565 (18)0.0744 (6)
C60.39058 (16)0.74627 (18)0.02664 (16)0.0684 (6)
C70.47228 (17)1.04284 (16)0.19502 (17)0.0722 (6)
C110.27194 (13)0.29537 (13)0.04021 (13)0.0426 (4)
C120.34504 (15)0.36973 (15)0.01837 (15)0.0558 (5)
C130.38423 (15)0.45618 (15)0.09022 (15)0.0576 (5)
C140.34859 (13)0.47393 (13)0.18692 (14)0.0468 (4)
C150.27948 (15)0.39957 (15)0.21315 (14)0.0534 (5)
C160.24227 (15)0.31224 (14)0.14145 (14)0.0526 (5)
O140.37876 (11)0.56258 (10)0.25684 (10)0.0604 (4)
H40.36611.00480.02110.084*
H50.32610.84000.11310.089*
H60.37240.67980.01120.082*
H70.45261.10920.15750.087*
H120.36840.36070.04750.067*
H130.43480.50280.07370.069*
H150.25750.40820.28000.064*
H160.19570.26290.16140.063*
H140.41190.60560.22700.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0546 (10)0.0565 (10)0.0546 (9)0.0030 (7)0.0087 (7)0.0013 (8)
C20.0406 (10)0.0500 (11)0.0574 (10)0.0001 (8)0.0194 (8)0.0015 (9)
C30.0491 (11)0.0567 (12)0.0699 (13)0.0070 (9)0.0250 (10)0.0130 (10)
C40.0582 (13)0.0783 (16)0.0756 (15)0.0101 (11)0.0197 (11)0.0276 (13)
C50.0633 (13)0.0963 (18)0.0585 (13)0.0013 (13)0.0070 (10)0.0201 (13)
C60.0640 (13)0.0784 (15)0.0570 (12)0.0089 (11)0.0056 (10)0.0025 (11)
C70.0861 (17)0.0481 (11)0.0932 (15)0.0081 (10)0.0430 (14)0.0108 (9)
C110.0476 (10)0.0404 (9)0.0421 (9)0.0035 (7)0.0160 (8)0.0020 (7)
C120.0650 (12)0.0560 (11)0.0551 (11)0.0083 (10)0.0314 (10)0.0111 (9)
C130.0605 (12)0.0568 (12)0.0623 (12)0.0138 (9)0.0284 (10)0.0117 (9)
C140.0483 (11)0.0464 (10)0.0433 (9)0.0014 (8)0.0077 (8)0.0061 (8)
C150.0693 (13)0.0545 (11)0.0401 (10)0.0039 (10)0.0206 (9)0.0020 (8)
C160.0668 (12)0.0492 (11)0.0458 (10)0.0075 (9)0.0218 (9)0.0031 (9)
O140.0701 (9)0.0575 (8)0.0556 (8)0.0096 (7)0.0201 (6)0.0160 (7)
Geometric parameters (Å, º) top
N1—C21.353 (2)C11—C11ii1.484 (3)
N1—C61.330 (2)C11—C121.389 (2)
C2—C2i1.444 (3)C11—C161.391 (2)
C2—C31.406 (2)C12—C131.375 (2)
C3—C41.398 (3)C13—C141.382 (2)
C3—C71.430 (3)C14—O141.3640 (19)
C4—C51.349 (3)C14—C151.372 (2)
C5—C61.391 (3)C15—C161.377 (2)
C7—C7i1.335 (4)
C6—N1—C2117.34 (16)C12—C11—C16115.66 (15)
N1—C2—C3122.42 (16)C12—C11—C11ii121.83 (18)
N1—C2—C2i118.70 (9)C16—C11—C11ii122.51 (19)
C3—C2—C2i118.89 (11)C13—C12—C11122.65 (16)
C4—C3—C2117.59 (18)C12—C13—C14120.10 (17)
C4—C3—C7122.18 (18)O14—C14—C15118.71 (15)
C2—C3—C7120.23 (17)O14—C14—C13122.74 (16)
C5—C4—C3120.05 (19)C15—C14—C13118.55 (16)
C4—C5—C6118.7 (2)C14—C15—C16120.62 (15)
N1—C6—C5123.8 (2)C15—C16—C11122.26 (16)
C7i—C7—C3120.88 (11)
C6—N1—C2—C32.4 (2)C2—C3—C7—C7i1.1 (3)
C6—N1—C2—C2i178.21 (19)C16—C11—C12—C131.4 (3)
N1—C2—C3—C41.3 (2)C11ii—C11—C12—C13178.07 (19)
C2i—C2—C3—C4179.26 (19)C11—C12—C13—C142.0 (3)
N1—C2—C3—C7178.76 (17)C12—C13—C14—O14175.22 (16)
C2i—C2—C3—C70.7 (3)C12—C13—C14—C154.4 (3)
C2—C3—C4—C50.9 (3)O14—C14—C15—C16176.33 (15)
C7—C3—C4—C5179.1 (2)C13—C14—C15—C163.3 (3)
C3—C4—C5—C61.8 (3)C14—C15—C16—C110.3 (3)
C2—N1—C6—C51.3 (3)C12—C11—C16—C152.6 (3)
C4—C5—C6—N10.8 (3)C11ii—C11—C16—C15176.92 (19)
C4—C3—C7—C7i178.8 (2)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N10.822.102.878 (2)159
C12—H12···O14iii0.932.583.403 (2)148
Symmetry code: (iii) x, y+1, z1/2.
(2) 4,4'-Thiodiphenol–1,10-phenanthroline (1/2) top
Crystal data top
C12H10O2S·2(C12H8N2)F(000) = 604
Mr = 578.69? #Insert any comments here.
Triclinic, P1Dx = 1.345 Mg m3
a = 7.7342 (5) ÅMo Kα radiation, λ = 0.7107 Å
b = 13.3624 (14) ÅCell parameters from 25 reflections
c = 14.9843 (11) Åθ = 9.6–18.6°
α = 110.514 (6)°µ = 0.16 mm1
β = 95.195 (6)°T = 294 K
γ = 95.895 (7)°Plate, colorless
V = 1429.3 (2) Å30.42 × 0.35 × 0.22 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
3431 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.000
Graphite monochromatorθmax = 25.2°, θmin = 2.0°
θ/2θ scansh = 99
Absorption correction: gaussian
ABSORB in NRCVAX (Gabe et al., 1989)
k = 016
Tmin = 0.946, Tmax = 0.970l = 1716
5184 measured reflections3 standard reflections every 120 min
5184 independent reflections intensity decay: no decay, variation 0.5%
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.100Calculated w = 1/[σ2(Fo2) + (0.0561P)2 + 0.0505P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5184 reflectionsΔρmax = 0.20 e Å3
391 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (2)
Crystal data top
C12H10O2S·2(C12H8N2)γ = 95.895 (7)°
Mr = 578.69V = 1429.3 (2) Å3
Triclinic, P1Z = 2
a = 7.7342 (5) ÅMo Kα radiation
b = 13.3624 (14) ŵ = 0.16 mm1
c = 14.9843 (11) ÅT = 294 K
α = 110.514 (6)°0.42 × 0.35 × 0.22 mm
β = 95.195 (6)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3431 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSORB in NRCVAX (Gabe et al., 1989)
Rint = 0.000
Tmin = 0.946, Tmax = 0.9703 standard reflections every 120 min
5184 measured reflections intensity decay: no decay, variation 0.5%
5184 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.04Δρmax = 0.20 e Å3
5184 reflectionsΔρmin = 0.20 e Å3
391 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data ex last SHELXL refinement cycles:

Equivalent position X, Y, 1+Z is represented by "_$1" Equivalent position 1+X, Y, 1+Z is represented by "_$2"

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.3694 (0.0057) x - 2.0612 (0.0154) y - 10.4299 (0.0094) z = 0.5325 (0.0031)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 0.0967 (0.0045) x - 12.8590 (0.0031) y + 8.7118 (0.0077) z = 0.5712 (0.0016)

Angle to previous plane (with approximate e.s.d.) = 83.97 (7)

* -0.0637 (0.0013) C11 * -0.0553 (0.0013) C12 * -0.0315 (0.0013) C13 * 0.0114 (0.0014) C14 * -0.0263 (0.0014) C15 * -0.0656 (0.0013) C16 * 0.1323 (0.0008) S1 * 0.0986 (0.0010) O14

Rms deviation of fitted atoms = 0.0711

5.3694 (0.0057) x - 2.0612 (0.0154) y - 10.4299 (0.0094) z = 0.5325 (0.0031)

Angle to previous plane (with approximate e.s.d.) = 83.97 (7)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 0.7552 (0.0050) x + 6.3615 (0.0039) y + 9.8018 (0.0043) z = 1.2464 (0.0015)

Angle to previous plane (with approximate e.s.d.) = 42.73 (7)

* 0.0529 (0.0013) C21 * 0.0373 (0.0012) C22 * -0.0245 (0.0013) C23 * -0.0242 (0.0014) C24 * -0.0046 (0.0013) C25 * 0.0121 (0.0013) C26 * -0.0501 (0.0008) S1 * 0.0010 (0.0011) O24

Rms deviation of fitted atoms = 0.0317

6.8549 (0.0015) x + 0.5658 (0.0029) y + 4.2342 (0.0048) z = 8.7640 (0.0025)

Angle to previous plane (with approximate e.s.d.) = 68.56 (4)

* -0.0111 (0.0012) N31 * -0.0050 (0.0013) C32 * 0.0041 (0.0014) C33 * 0.0178 (0.0016) C34 * 0.0040 (0.0016) C35 * -0.0110 (0.0015) C36 * 0.0057 (0.0014) C37 * 0.0024 (0.0012) N41 * -0.0070 (0.0013) C42 * -0.0114 (0.0014) C43 * -0.0148 (0.0014) C44 * 0.0093 (0.0015) C45 * 0.0204 (0.0014) C46 * -0.0031 (0.0014) C47 - 3.3465 (0.0020) N51_$1 - 3.3833 (0.0018) C52_$1 - 3.4187 (0.0018) C53_$1 - 3.4050 (0.0023) C54_$1 - 3.3891 (0.0026) C55_$1 - 3.3624 (0.0026) C56_$1 - 3.4999 (0.0019) C57_$1 - 3.3402 (0.0018) N61_$1 - 3.4134 (0.0017) C62_$1 - 3.5317 (0.0017) C63_$1 - 3.5990 (0.0021) C64_$1 - 3.5360 (0.0023) C65_$1 - 3.3971 (0.0024) C66_$1 - 3.5716 (0.0019) C67_$1

Rms deviation of fitted atoms = 0.0106

7.0177 (0.0014) x + 0.6706 (0.0039) y + 3.4781 (0.0057) z = 4.8711 (0.0032)

Angle to previous plane (with approximate e.s.d.) = 3.08 (4)

* -0.0094 (0.0013) N51_$1 * 0.0260 (0.0014) C52_$1 * 0.0365 (0.0015) C53_$1 * 0.0183 (0.0017) C54_$1 * -0.0382 (0.0018) C55_$1 * -0.0528 (0.0016) C56_$1 * 0.0307 (0.0015) C57_$1 * 0.0547 (0.0014) N61_$1 * 0.0269 (0.0014) C62_$1 * -0.0163 (0.0015) C63_$1 * -0.0556 (0.0017) C64_$1 * -0.0369 (0.0019) C65_$1 * 0.0282 (0.0017) C66_$1 * -0.0120 (0.0016) C67_$1

Rms deviation of fitted atoms = 0.0348

6.8549 (0.0015) x + 0.5658 (0.0029) y + 4.2342 (0.0048) z = 8.7640 (0.0025)

Angle to previous plane (with approximate e.s.d.) = 3.08 (4)

* -0.0111 (0.0012) N31 * -0.0050 (0.0013) C32 * 0.0041 (0.0014) C33 * 0.0178 (0.0016) C34 * 0.0040 (0.0016) C35 * -0.0110 (0.0015) C36 * 0.0057 (0.0014) C37 * 0.0024 (0.0012) N41 * -0.0070 (0.0013) C42 * -0.0114 (0.0014) C43 * -0.0148 (0.0014) C44 * 0.0093 (0.0015) C45 * 0.0204 (0.0014) C46 * -0.0031 (0.0014) C47 3.5084 (0.0015) N51_$2 3.4715 (0.0016) C52_$2 3.4362 (0.0018) C53_$2 3.4498 (0.0020) C54_$2 3.4658 (0.0022) C55_$2 3.4924 (0.0021) C56_$2 3.3550 (0.0021) C57_$2 3.5146 (0.0017) N61_$2 3.4415 (0.0017) C62_$2 3.3232 (0.0020) C63_$2 3.2559 (0.0024) C64_$2 3.3189 (0.0026) C65_$2 3.4577 (0.0024) C66_$2 3.2833 (0.0023) C67_$2

Rms deviation of fitted atoms = 0.0106

7.0177 (0.0014) x + 0.6706 (0.0039) y + 3.4781 (0.0057) z = 11.8888 (0.0026)

Angle to previous plane (with approximate e.s.d.) = 3.08 (4)

* -0.0094 (0.0013) N51_$2 * 0.0260 (0.0014) C52_$2 * 0.0365 (0.0015) C53_$2 * 0.0183 (0.0017) C54_$2 * -0.0382 (0.0018) C55_$2 * -0.0528 (0.0016) C56_$2 * 0.0307 (0.0015) C57_$2 * 0.0547 (0.0014) N61_$2 * 0.0269 (0.0014) C62_$2 * -0.0163 (0.0015) C63_$2 * -0.0556 (0.0017) C64_$2 * -0.0369 (0.0019) C65_$2 * 0.0282 (0.0017) C66_$2 * -0.0120 (0.0016) C67_$2

Rms deviation of fitted atoms = 0.0348

6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 2.55 (6)

* 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 3.5069 (0.0021) N51_$2 3.4822 (0.0020) C52_$2 3.4585 (0.0026) C53_$2 3.4707 (0.0034) C54_$2 3.3898 (0.0030) C57_$2 3.5151 (0.0017) N61_$2 3.4533 (0.0018) C62_$2 3.3476 (0.0024) C63_$2 3.2810 (0.0030) C64_$2 3.3192 (0.0030) C67_$2

Rms deviation of fitted atoms = 0.0029

6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 1.24 (8)

* -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 3.5316 (0.0022) N51_$2 3.4808 (0.0021) C52_$2 3.4309 (0.0019) C53_$2 3.4449 (0.0021) C54_$2 3.3354 (0.0025) C57_$2 3.5381 (0.0033) N61_$2 3.4508 (0.0028) C62_$2 3.3181 (0.0032) C63_$2 3.2514 (0.0040) C64_$2 3.2638 (0.0031) C67_$2

Rms deviation of fitted atoms = 0.0047

6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 1.24 (8)

* 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 - 3.3726 (0.0040) N51_$1 - 3.3972 (0.0034) C52_$1 - 3.4210 (0.0037) C53_$1 - 3.4088 (0.0047) C54_$1 - 3.4897 (0.0035) C57_$1 - 3.3644 (0.0026) N61_$1 - 3.4262 (0.0026) C62_$1 - 3.5319 (0.0022) C63_$1 - 3.5985 (0.0022) C64_$1 - 3.5603 (0.0028) C67_$1

Rms deviation of fitted atoms = 0.0029

6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 1.24 (8)

* -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 - 3.2955 (0.0032) N51_$1 - 3.3463 (0.0026) C52_$1 - 3.3962 (0.0023) C53_$1 - 3.3822 (0.0029) C54_$1 - 3.4917 (0.0020) C57_$1 - 3.2890 (0.0033) N61_$1 - 3.3763 (0.0026) C62_$1 - 3.5090 (0.0023) C63_$1 - 3.5758 (0.0030) C64_$1 - 3.5633 (0.0021) C67_$1

Rms deviation of fitted atoms = 0.0047

6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 1.24 (8)

* 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 3.5069 (0.0021) N51_$2 3.4822 (0.0020) C52_$2 3.4585 (0.0026) C53_$2 3.4707 (0.0034) C54_$2 3.3898 (0.0030) C57_$2 3.5151 (0.0017) N61_$2 3.4533 (0.0018) C62_$2 3.3476 (0.0024) C63_$2 3.2810 (0.0030) C64_$2 3.3192 (0.0030) C67_$2

Rms deviation of fitted atoms = 0.0029

6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 1.24 (8)

* -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 3.5316 (0.0022) N51_$2 3.4808 (0.0021) C52_$2 3.4309 (0.0019) C53_$2 3.4449 (0.0021) C54_$2 3.3354 (0.0025) C57_$2 3.5381 (0.0033) N61_$2 3.4508 (0.0028) C62_$2 3.3181 (0.0032) C63_$2 3.2514 (0.0040) C64_$2 3.2638 (0.0031) C67_$2

Rms deviation of fitted atoms = 0.0047

6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 0.0

* -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47

Rms deviation of fitted atoms = 0.0047

6.9040 (0.0027) x + 0.7551 (0.0092) y + 3.8962 (0.0103) z = 1.3218 (0.0056)

Angle to previous plane (with approximate e.s.d.) = 2.06 (8)

* 0.0077 (0.0011) N51 * -0.0017 (0.0011) C52 * -0.0063 (0.0011) C53 * 0.0087 (0.0014) C54 * -0.0029 (0.0015) C55 * -0.0056 (0.0014) C56 - 0.0596 (0.0027) C57

Rms deviation of fitted atoms = 0.0060

7.1357 (0.0024) x + 0.6236 (0.0102) y + 2.9632 (0.0108) z = 1.5987 (0.0052)

Angle to previous plane (with approximate e.s.d.) = 4.22 (8)

* -0.0006 (0.0012) N61 * -0.0055 (0.0011) C62 * 0.0062 (0.0012) C63 * -0.0013 (0.0014) C64 * -0.0046 (0.0016) C65 * 0.0057 (0.0015) C66 0.0314 (0.0028) C67

Rms deviation of fitted atoms = 0.0045

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.36375 (7)0.03072 (4)0.13013 (4)0.07258 (19)
O140.99514 (15)0.22322 (11)0.41741 (8)0.0663 (4)
O240.08412 (17)0.30651 (13)0.06518 (10)0.0772 (4)
C110.5529 (2)0.10110 (13)0.21361 (12)0.0538 (4)
C120.5377 (2)0.16396 (15)0.30720 (12)0.0591 (5)
C130.6831 (2)0.20743 (15)0.37570 (12)0.0575 (4)
C140.8485 (2)0.18691 (14)0.35218 (11)0.0515 (4)
C150.8649 (2)0.12613 (15)0.25832 (12)0.0618 (5)
C160.7188 (3)0.08397 (15)0.18996 (12)0.0620 (5)
C210.2941 (2)0.12155 (13)0.07634 (10)0.0483 (4)
C220.1162 (2)0.12248 (14)0.06042 (11)0.0549 (4)
C230.0488 (2)0.18181 (15)0.01042 (12)0.0575 (5)
C240.1594 (2)0.24503 (14)0.02205 (11)0.0531 (4)
C250.3385 (2)0.24510 (14)0.00630 (12)0.0551 (4)
C260.4046 (2)0.18255 (14)0.04110 (12)0.0536 (4)
N310.89380 (18)0.22912 (11)0.58957 (10)0.0525 (4)
C320.84012 (19)0.30006 (13)0.66846 (11)0.0449 (4)
C330.7962 (2)0.27033 (14)0.74569 (12)0.0521 (4)
C340.8110 (3)0.16413 (16)0.73920 (15)0.0684 (5)
C350.8638 (3)0.09403 (16)0.65972 (16)0.0727 (6)
C360.9037 (2)0.13053 (15)0.58673 (14)0.0647 (5)
C370.7403 (2)0.34799 (16)0.82617 (12)0.0598 (5)
N410.87423 (17)0.43519 (11)0.59691 (9)0.0510 (3)
C420.82876 (19)0.40831 (13)0.67189 (10)0.0437 (4)
C430.77184 (19)0.48229 (13)0.75312 (11)0.0480 (4)
C440.7622 (2)0.58675 (14)0.75393 (13)0.0578 (5)
C450.8095 (2)0.61360 (15)0.67954 (14)0.0618 (5)
C460.8647 (2)0.53572 (15)0.60317 (13)0.0576 (4)
C470.7284 (2)0.44886 (16)0.82991 (12)0.0582 (5)
N510.23204 (19)0.43628 (13)0.15447 (10)0.0608 (4)
C520.2832 (2)0.41071 (13)0.24258 (12)0.0487 (4)
C530.3006 (2)0.48535 (14)0.28915 (13)0.0558 (4)
C540.2639 (3)0.58927 (17)0.2404 (2)0.0781 (6)
C550.2102 (3)0.61362 (18)0.1529 (2)0.0868 (7)
C560.1955 (3)0.53514 (19)0.11229 (16)0.0777 (6)
C570.3494 (2)0.45268 (18)0.38288 (15)0.0684 (5)
N610.3047 (2)0.23299 (13)0.24347 (12)0.0657 (4)
C620.3178 (2)0.30195 (14)0.29116 (12)0.0504 (4)
C630.3610 (2)0.27259 (15)0.38517 (13)0.0579 (5)
C640.3883 (3)0.16648 (19)0.43103 (17)0.0796 (6)
C650.3748 (3)0.09661 (19)0.3850 (2)0.0900 (7)
C660.3342 (3)0.13232 (18)0.2912 (2)0.0868 (7)
C670.3761 (2)0.35096 (19)0.42946 (14)0.0698 (5)
H140.96760.24670.47170.099*
H240.15750.33260.09010.116*
H120.42720.17710.32420.071*
H130.67030.25070.43800.069*
H150.97540.11350.24110.074*
H160.73200.04340.12700.074*
H220.04020.08220.08390.066*
H230.07200.17920.00150.069*
H250.41460.28750.02780.066*
H260.52490.18140.04950.064*
H340.78460.14180.78930.082*
H350.87310.02340.65430.087*
H360.93960.08210.53250.078*
H370.71140.32840.87730.072*
H440.72340.63760.80550.069*
H450.80500.68290.67970.074*
H460.89740.55550.55270.069*
H470.69120.49770.88340.070*
H540.27640.64150.26810.094*
H550.18340.68220.12030.104*
H560.15790.55290.05210.093*
H570.36310.50290.41270.082*
H640.41580.14390.49350.095*
H650.39240.02540.41530.108*
H660.32720.08330.26000.104*
H670.40490.33130.49160.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0902 (4)0.0529 (3)0.0697 (3)0.0112 (2)0.0169 (3)0.0289 (2)
O140.0625 (8)0.0841 (9)0.0474 (7)0.0028 (7)0.0056 (6)0.0203 (7)
O240.0680 (8)0.1062 (11)0.0761 (9)0.0238 (8)0.0078 (7)0.0536 (8)
C110.0704 (11)0.0466 (10)0.0471 (9)0.0026 (8)0.0007 (8)0.0236 (8)
C120.0641 (11)0.0640 (12)0.0545 (11)0.0191 (9)0.0082 (9)0.0253 (9)
C130.0704 (12)0.0613 (11)0.0405 (9)0.0175 (9)0.0081 (8)0.0156 (8)
C140.0602 (10)0.0551 (10)0.0438 (9)0.0034 (8)0.0071 (8)0.0250 (8)
C150.0639 (11)0.0757 (13)0.0461 (10)0.0062 (9)0.0163 (8)0.0215 (9)
C160.0816 (13)0.0619 (12)0.0400 (9)0.0045 (10)0.0129 (9)0.0161 (8)
C210.0597 (10)0.0439 (9)0.0334 (8)0.0011 (7)0.0026 (7)0.0078 (7)
C220.0598 (11)0.0570 (11)0.0417 (9)0.0046 (8)0.0136 (8)0.0122 (8)
C230.0460 (9)0.0733 (12)0.0471 (10)0.0057 (9)0.0086 (8)0.0146 (9)
C240.0555 (10)0.0642 (11)0.0381 (8)0.0109 (8)0.0053 (7)0.0162 (8)
C250.0521 (10)0.0656 (11)0.0522 (10)0.0029 (8)0.0101 (8)0.0279 (9)
C260.0478 (9)0.0601 (11)0.0513 (10)0.0043 (8)0.0035 (7)0.0201 (8)
N310.0577 (8)0.0472 (9)0.0487 (8)0.0141 (7)0.0004 (6)0.0125 (7)
C320.0398 (8)0.0505 (10)0.0393 (8)0.0039 (7)0.0054 (6)0.0133 (7)
C330.0485 (9)0.0584 (11)0.0474 (9)0.0002 (8)0.0060 (7)0.0219 (8)
C340.0718 (12)0.0699 (13)0.0692 (13)0.0017 (10)0.0071 (10)0.0394 (11)
C350.0819 (14)0.0515 (12)0.0836 (15)0.0099 (10)0.0077 (11)0.0278 (11)
C360.0710 (12)0.0535 (12)0.0652 (12)0.0153 (9)0.0011 (9)0.0169 (9)
C370.0597 (11)0.0762 (13)0.0429 (9)0.0017 (9)0.0025 (8)0.0249 (9)
N410.0569 (8)0.0538 (9)0.0434 (8)0.0110 (7)0.0040 (6)0.0190 (6)
C420.0389 (8)0.0513 (9)0.0369 (8)0.0054 (7)0.0031 (6)0.0133 (7)
C430.0418 (9)0.0525 (10)0.0407 (9)0.0044 (7)0.0016 (7)0.0084 (7)
C440.0550 (10)0.0500 (11)0.0567 (11)0.0099 (8)0.0042 (8)0.0054 (8)
C450.0643 (11)0.0503 (11)0.0693 (12)0.0109 (9)0.0039 (9)0.0204 (10)
C460.0636 (11)0.0593 (12)0.0544 (10)0.0104 (9)0.0037 (8)0.0268 (9)
C470.0544 (10)0.0727 (13)0.0392 (9)0.0061 (9)0.0053 (7)0.0113 (8)
N510.0583 (9)0.0650 (10)0.0517 (9)0.0088 (7)0.0004 (7)0.0141 (8)
C520.0404 (9)0.0520 (10)0.0510 (10)0.0043 (7)0.0051 (7)0.0185 (8)
C530.0443 (9)0.0531 (11)0.0714 (12)0.0042 (8)0.0051 (8)0.0283 (9)
C540.0597 (12)0.0585 (13)0.1169 (19)0.0059 (10)0.0052 (12)0.0377 (13)
C550.0708 (14)0.0538 (13)0.115 (2)0.0098 (10)0.0047 (13)0.0069 (14)
C560.0671 (13)0.0764 (15)0.0657 (13)0.0090 (11)0.0017 (10)0.0015 (12)
C570.0601 (12)0.0847 (15)0.0745 (13)0.0052 (10)0.0011 (10)0.0494 (12)
N610.0647 (10)0.0595 (10)0.0823 (11)0.0081 (8)0.0040 (8)0.0390 (9)
C620.0413 (9)0.0531 (10)0.0569 (10)0.0034 (7)0.0039 (7)0.0236 (8)
C630.0447 (9)0.0633 (12)0.0578 (11)0.0082 (8)0.0005 (8)0.0136 (9)
C640.0660 (13)0.0735 (15)0.0818 (15)0.0112 (11)0.0078 (11)0.0071 (12)
C650.0713 (14)0.0582 (14)0.120 (2)0.0146 (11)0.0092 (14)0.0075 (14)
C660.0745 (14)0.0609 (14)0.136 (2)0.0083 (11)0.0023 (14)0.0531 (15)
C670.0608 (12)0.0975 (17)0.0549 (11)0.0085 (11)0.0070 (9)0.0332 (12)
Geometric parameters (Å, º) top
O14—C141.353 (2)C37—C471.342 (3)
S1—C111.7751 (18)N41—C421.358 (2)
O24—C241.354 (2)N41—C461.324 (2)
S1—C211.7760 (17)C42—C431.413 (2)
C11—C121.382 (2)C43—C441.401 (2)
C11—C161.382 (3)C43—C471.427 (2)
C12—C131.376 (2)C44—C451.353 (3)
C13—C141.387 (2)C45—C461.386 (2)
C14—C151.381 (2)N51—C521.350 (2)
C15—C161.378 (2)N51—C561.322 (3)
C21—C221.377 (2)C52—C531.406 (2)
C21—C261.383 (2)C52—C621.445 (2)
C22—C231.375 (2)C53—C541.396 (3)
C23—C241.377 (2)C53—C571.416 (3)
C24—C251.384 (2)C54—C551.352 (3)
C25—C261.379 (2)C55—C561.385 (3)
N31—C321.361 (2)C57—C671.340 (3)
N31—C361.314 (2)N61—C621.351 (2)
C32—C331.406 (2)N61—C661.339 (3)
C32—C421.441 (2)C62—C631.405 (2)
C33—C341.405 (3)C63—C641.390 (3)
C33—C371.424 (2)C63—C671.424 (3)
C34—C351.359 (3)C64—C651.342 (3)
C35—C361.390 (3)C65—C661.394 (3)
C11—S1—C21106.28 (8)N41—C42—C32118.52 (14)
O14—C14—C13122.87 (15)N41—C42—C43122.63 (15)
O14—C14—C15118.34 (16)C32—C42—C43118.85 (14)
O24—C24—C23116.95 (15)C42—C43—C44117.27 (16)
O24—C24—C25124.04 (16)C42—C43—C47119.60 (16)
S1—C11—C12120.75 (15)C44—C43—C47123.12 (16)
S1—C11—C16120.57 (14)C43—C44—C45119.93 (17)
C16—C11—C12118.22 (16)C44—C45—C46118.68 (17)
C11—C12—C13121.21 (17)N41—C46—C45124.61 (17)
C12—C13—C14120.21 (16)C37—C47—C43121.04 (16)
C13—C14—C15118.78 (16)C52—N51—C56117.74 (17)
C14—C15—C16120.57 (17)N51—C52—C53122.40 (16)
C11—C16—C15120.95 (16)N51—C52—C62118.49 (15)
S1—C21—C22117.08 (12)C53—C52—C62119.10 (16)
S1—C21—C26124.31 (14)C52—C53—C54117.43 (19)
C22—C21—C26118.27 (15)C52—C53—C57119.76 (17)
C21—C22—C23121.27 (15)C54—C53—C57122.80 (19)
C22—C23—C24120.32 (16)C53—C54—C55119.7 (2)
C23—C24—C25118.98 (16)C54—C55—C56119.2 (2)
C24—C25—C26120.29 (16)N51—C56—C55123.5 (2)
C21—C26—C25120.80 (16)C53—C57—C67121.36 (18)
C32—N31—C36118.18 (15)C62—N61—C66116.15 (18)
N31—C32—C33121.79 (15)N61—C62—C52117.69 (16)
N31—C32—C42118.42 (14)N61—C62—C63123.30 (17)
C33—C32—C42119.79 (15)C52—C62—C63119.01 (15)
C32—C33—C34117.57 (17)C62—C63—C64117.61 (19)
C32—C33—C37119.24 (16)C62—C63—C67119.73 (17)
C34—C33—C37123.19 (17)C64—C63—C67122.7 (2)
C33—C34—C35119.96 (18)C63—C64—C65119.9 (2)
C34—C35—C36118.41 (18)C64—C65—C66119.1 (2)
N31—C36—C35124.08 (19)N61—C66—C65123.9 (2)
C33—C37—C47121.48 (16)C57—C67—C63120.99 (18)
C42—N41—C46116.86 (14)
C11—S1—C21—C22139.81 (13)N41—C42—C43—C440.4 (2)
C11—S1—C21—C2646.95 (16)C32—C42—C43—C44179.93 (13)
C21—S1—C11—C1288.13 (15)N41—C42—C43—C47179.16 (14)
C21—S1—C11—C1699.74 (15)C32—C42—C43—C470.5 (2)
C16—C11—C12—C130.9 (3)C42—C43—C44—C451.1 (2)
S1—C11—C12—C13171.46 (13)C47—C43—C44—C45178.43 (16)
C11—C12—C13—C141.3 (3)C43—C44—C45—C460.8 (3)
C12—C13—C14—O14176.86 (15)C42—N41—C46—C451.0 (2)
C12—C13—C14—C152.6 (3)C44—C45—C46—N410.3 (3)
O14—C14—C15—C16177.62 (16)C33—C37—C47—C430.1 (3)
C13—C14—C15—C161.9 (3)C44—C43—C47—C37179.71 (16)
C14—C15—C16—C110.2 (3)C42—C43—C47—C370.2 (2)
C12—C11—C16—C151.6 (3)C56—N51—C52—C530.9 (2)
S1—C11—C16—C15170.73 (14)C56—N51—C52—C62177.89 (15)
C26—C21—C22—C230.3 (2)N51—C52—C53—C540.4 (2)
S1—C21—C22—C23173.31 (13)C62—C52—C53—C54179.21 (15)
C21—C22—C23—C242.3 (3)N51—C52—C53—C57177.97 (15)
C22—C23—C24—O24175.82 (16)C62—C52—C53—C570.8 (2)
C22—C23—C24—C252.1 (2)C52—C53—C54—C551.5 (3)
O24—C24—C25—C26177.83 (17)C57—C53—C54—C55176.91 (18)
C23—C24—C25—C260.1 (3)C53—C54—C55—C561.1 (3)
C24—C25—C26—C212.1 (3)C52—N51—C56—C551.3 (3)
C22—C21—C26—C251.8 (2)C54—C55—C56—N510.3 (3)
S1—C21—C26—C25175.01 (13)C54—C53—C57—C67176.96 (17)
C36—N31—C32—C330.1 (2)C52—C53—C57—C671.4 (3)
C36—N31—C32—C42179.91 (14)C66—N61—C62—C630.5 (2)
N31—C32—C33—C340.5 (2)C66—N61—C62—C52178.73 (16)
C42—C32—C33—C34179.45 (14)N51—C52—C62—N613.0 (2)
N31—C32—C33—C37179.79 (14)C53—C52—C62—N61178.18 (14)
C42—C32—C33—C370.3 (2)N51—C52—C62—C63176.27 (14)
C32—C33—C34—C350.9 (3)C53—C52—C62—C632.5 (2)
C37—C33—C34—C35179.45 (16)N61—C62—C63—C641.2 (2)
C33—C34—C35—C360.6 (3)C52—C62—C63—C64178.07 (15)
C32—N31—C36—C350.4 (3)N61—C62—C63—C67178.54 (15)
C34—C35—C36—N310.1 (3)C52—C62—C63—C672.2 (2)
C34—C33—C37—C47179.77 (17)C62—C63—C64—C650.7 (3)
C32—C33—C37—C470.1 (2)C67—C63—C64—C65178.98 (19)
C46—N41—C42—C430.6 (2)C63—C64—C65—C660.3 (3)
C46—N41—C42—C32179.02 (14)C62—N61—C66—C650.6 (3)
N31—C32—C42—N410.8 (2)C64—C65—C66—N611.0 (3)
C33—C32—C42—N41179.13 (13)C53—C57—C67—C631.7 (3)
N31—C32—C42—C43179.50 (13)C64—C63—C67—C57179.78 (18)
C33—C32—C42—C430.5 (2)C62—C63—C67—C570.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.821.992.741 (2)153
O24—H24···N510.822.012.757 (2)151
(3) 4,4'-Sulfonyldiphenol–1,10-phenanthroline (2/3) top
Crystal data top
2(C12H10O4S)·3(C12H8N2)? #Insert any comments here.
Mr = 1041.13Dx = 1.398 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
a = 15.8692 (16) ÅCell parameters from 25 reflections
b = 24.3728 (17) Åθ = 10.2–18.3°
c = 13.0952 (9) ŵ = 0.18 mm1
β = 102.362 (8)°T = 294 K
V = 4947.5 (7) Å3Plate, colorless
Z = 40.42 × 0.38 × 0.10 mm
F(000) = 2168
Data collection top
Enraf-Nonius CAD-4
diffractometer
3182 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.006
Graphite monochromatorθmax = 25.1°, θmin = 2.0°
θ/2θ scansh = 1818
Absorption correction: gaussian
ABSORB in NRCVAX (Gabe et al., 1989)
k = 029
Tmin = 0.937, Tmax = 0.983l = 015
4636 measured reflections3 standard reflections every 120 min
4434 independent reflections intensity decay: 1.7%
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.104Calculated w = 1/[σ2(Fo2) + (0.0534P)2 + 1.3074P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4434 reflectionsΔρmax = 0.22 e Å3
346 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00124 (18)
Crystal data top
2(C12H10O4S)·3(C12H8N2)V = 4947.5 (7) Å3
Mr = 1041.13Z = 4
Monoclinic, C2/cMo Kα radiation
a = 15.8692 (16) ŵ = 0.18 mm1
b = 24.3728 (17) ÅT = 294 K
c = 13.0952 (9) Å0.42 × 0.38 × 0.10 mm
β = 102.362 (8)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3182 reflections with I > 2σ(I)
Absorption correction: gaussian
ABSORB in NRCVAX (Gabe et al., 1989)
Rint = 0.006
Tmin = 0.937, Tmax = 0.9833 standard reflections every 120 min
4636 measured reflections intensity decay: 1.7%
4434 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
4434 reflectionsΔρmin = 0.30 e Å3
346 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean-plane data ex SHELXL refinement cycles.

Equivalent position denoted by "$1" is at 1 - x, y, 0.5 - z

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 4.2301 (0.0181) x + 22.4954 (0.0088) y + 4.2984 (0.0152) z = 10.6931 (0.0078)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

0.7156 (0.0116) x + 5.2728 (0.0130) y + 12.3489 (0.0041) z = 3.9077 (0.0092)

Angle to previous plane (with approximate e.s.d.) = 62.72 (8)

* 0.0453 (0.0016) C11 * 0.0550 (0.0015) C12 * 0.0347 (0.0015) C13 * -0.0222 (0.0018) C14 * 0.0281 (0.0016) C15 * 0.0640 (0.0016) C16 * -0.1180 (0.0009) S1 * -0.0868 (0.0012) O14

Rms deviation of fitted atoms = 0.0643

- 4.2301 (0.0181) x + 22.4954 (0.0088) y + 4.2984 (0.0152) z = 10.6931 (0.0078)

Angle to previous plane (with approximate e.s.d.) = 62.72 (8)

* 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12

Rms deviation of fitted atoms = 0.0000

- 14.2444 (0.0068) x + 9.2758 (0.0154) y - 0.3281 (0.0100) z = 0.4586 (0.0098)

Angle to previous plane (with approximate e.s.d.) = 58.08 (8)

* -0.0213 (0.0016) C21 * -0.0261 (0.0017) C22 * -0.0086 (0.0019) C23 * 0.0110 (0.0020) C24 * -0.0029 (0.0017) C25 * -0.0291 (0.0016) C26 * 0.0485 (0.0011) S1 * 0.0284 (0.0016) O24

Rms deviation of fitted atoms = 0.0258

12.4411 (0.0099) x - 1.7307 (0.0224) y - 10.0866 (0.0085) z = 3.4231 (0.0064)

Angle to previous plane (with approximate e.s.d.) = 53.59 (6)

* 0.0011 (0.0015) N31 * -0.0177 (0.0015) C32 * 0.0170 (0.0015) C33 * -0.0008 (0.0017) C34 * -0.0155 (0.0018) C35 * 0.0160 (0.0018) C36 0.1085 (0.0039) C37 - 0.0419 (0.0043) C32_$1 0.1811 (0.0045) C37_$1

Rms deviation of fitted atoms = 0.0135

12.4411 (0.0099) x + 1.7307 (0.0224) y - 10.0866 (0.0085) z = 3.9747 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 8.14 (12)

* -0.0011 (0.0015) N31_$1 * 0.0177 (0.0015) C32_$1 * -0.0170 (0.0015) C33_$1 * 0.0008 (0.0017) C34_$1 * 0.0155 (0.0018) C35_$1 * -0.0160 (0.0018) C36_$1 - 0.1085 (0.0039) C37_$1

Rms deviation of fitted atoms = 0.0135

11.5438 (0.0114) x + 0.0924 (0.0234) y - 10.8165 (0.0078) z = 1.4284 (0.0215)

Angle to previous plane (with approximate e.s.d.) = 6.42 (13)

* 0.0016 (0.0017) N41 * 0.0078 (0.0015) C42 * -0.0124 (0.0015) C43 * 0.0084 (0.0017) C44 * 0.0008 (0.0019) C45 * -0.0062 (0.0019) C46 - 0.0592 (0.0037) C47

Rms deviation of fitted atoms = 0.0074

11.9984 (0.0105) x + 1.0322 (0.0246) y - 10.4739 (0.0079) z = 2.5886 (0.0216)

Angle to previous plane (with approximate e.s.d.) = 3.34 (13)

* 0.0030 (0.0017) N51 * -0.0084 (0.0016) C52 * 0.0066 (0.0016) C53 * 0.0000 (0.0018) C54 * -0.0051 (0.0020) C55 * 0.0038 (0.0020) C56 0.0139 (0.0038) C57

Rms deviation of fitted atoms = 0.0052

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.30076 (3)0.51893 (2)0.06788 (4)0.03971 (16)
O110.21571 (9)0.50137 (6)0.07611 (13)0.0542 (4)
O120.31144 (10)0.53995 (6)0.03161 (11)0.0537 (4)
O140.52449 (9)0.32527 (6)0.14013 (13)0.0519 (4)
O240.40470 (15)0.68772 (7)0.38834 (14)0.0788 (6)
C110.36983 (12)0.46251 (7)0.10120 (15)0.0348 (4)
C120.33602 (13)0.41287 (8)0.12514 (15)0.0366 (5)
C130.38733 (13)0.36666 (8)0.14025 (16)0.0410 (5)
C140.47214 (13)0.36959 (8)0.12947 (16)0.0400 (5)
C150.50681 (14)0.41987 (8)0.11007 (17)0.0438 (5)
C160.45568 (14)0.46615 (8)0.09618 (16)0.0419 (5)
C210.33627 (12)0.56929 (7)0.16260 (16)0.0373 (5)
C220.32840 (15)0.56028 (8)0.26461 (18)0.0486 (6)
C230.35180 (16)0.60072 (9)0.33827 (18)0.0545 (6)
C240.38339 (15)0.65037 (8)0.31102 (18)0.0500 (6)
C250.39243 (14)0.65918 (8)0.20995 (18)0.0464 (5)
C260.36950 (13)0.61855 (8)0.13610 (17)0.0427 (5)
N310.43551 (11)0.22495 (6)0.15909 (14)0.0454 (5)
C320.46443 (12)0.17660 (7)0.20493 (16)0.0366 (5)
C330.42827 (13)0.12595 (8)0.16557 (17)0.0435 (5)
C340.35779 (14)0.12676 (9)0.08027 (19)0.0525 (6)
C350.32814 (15)0.17518 (10)0.0368 (2)0.0594 (7)
C360.37003 (15)0.22315 (9)0.07717 (19)0.0571 (6)
C370.46525 (16)0.07569 (8)0.21074 (19)0.0561 (6)
N410.39058 (13)0.79510 (7)0.29143 (16)0.0587 (5)
C420.43405 (14)0.83940 (8)0.33762 (17)0.0432 (5)
C430.40639 (13)0.89354 (8)0.31043 (17)0.0430 (5)
C440.33280 (15)0.90033 (10)0.23003 (19)0.0543 (6)
C450.28969 (16)0.85595 (11)0.1843 (2)0.0650 (7)
C460.32111 (17)0.80426 (11)0.2181 (2)0.0696 (7)
C470.45315 (15)0.93845 (9)0.36505 (19)0.0509 (6)
N510.53579 (13)0.77841 (7)0.44305 (17)0.0573 (5)
C520.50987 (13)0.83069 (8)0.41960 (17)0.0437 (5)
C530.55290 (13)0.87631 (8)0.47196 (18)0.0453 (5)
C540.62420 (15)0.86635 (10)0.5533 (2)0.0585 (6)
C550.64958 (16)0.81401 (11)0.5777 (2)0.0700 (8)
C560.60375 (17)0.77131 (10)0.5201 (2)0.0696 (8)
C570.52271 (15)0.93050 (9)0.44202 (19)0.0521 (6)
H140.49770.29810.15190.078*
H240.41470.71730.36350.118*
H120.27870.41070.13100.044*
H130.36500.33350.15770.049*
H150.56460.42230.10640.053*
H160.47900.49980.08340.050*
H220.30730.52700.28310.058*
H230.34640.59470.40670.065*
H250.41390.69240.19170.056*
H260.37640.62420.06810.051*
H340.33160.09410.05370.063*
H350.28070.17650.01890.071*
H360.35080.25610.04450.069*
H370.44060.04250.18510.067*
H440.31380.93540.20830.065*
H450.24030.85980.13180.078*
H460.29080.77390.18650.083*
H470.43500.97410.34680.061*
H540.65400.89550.59040.070*
H550.69670.80670.63180.084*
H560.62220.73560.53710.084*
H570.55170.96060.47640.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0414 (3)0.0326 (3)0.0410 (3)0.0001 (2)0.0006 (2)0.0005 (2)
O110.0388 (8)0.0420 (8)0.0766 (12)0.0023 (7)0.0010 (7)0.0023 (8)
O120.0722 (10)0.0470 (9)0.0366 (9)0.0024 (7)0.0001 (7)0.0064 (7)
O140.0527 (9)0.0367 (8)0.0617 (11)0.0067 (7)0.0017 (8)0.0053 (8)
O240.1305 (17)0.0460 (10)0.0591 (12)0.0276 (11)0.0183 (11)0.0170 (9)
C110.0391 (11)0.0315 (10)0.0314 (11)0.0018 (8)0.0019 (8)0.0023 (8)
C120.0370 (11)0.0362 (11)0.0350 (12)0.0033 (8)0.0041 (9)0.0001 (9)
C130.0479 (12)0.0313 (10)0.0404 (12)0.0068 (9)0.0020 (9)0.0010 (9)
C140.0450 (12)0.0352 (10)0.0361 (12)0.0038 (9)0.0003 (9)0.0042 (9)
C150.0391 (11)0.0461 (12)0.0460 (13)0.0005 (9)0.0090 (10)0.0008 (10)
C160.0485 (12)0.0348 (11)0.0422 (12)0.0066 (9)0.0091 (10)0.0017 (9)
C210.0397 (11)0.0300 (10)0.0402 (12)0.0022 (8)0.0042 (9)0.0004 (9)
C220.0637 (14)0.0320 (11)0.0500 (14)0.0088 (10)0.0118 (11)0.0027 (10)
C230.0807 (17)0.0419 (12)0.0413 (13)0.0106 (12)0.0137 (12)0.0018 (10)
C240.0618 (14)0.0356 (11)0.0487 (14)0.0047 (10)0.0034 (11)0.0069 (10)
C250.0547 (13)0.0300 (11)0.0520 (14)0.0051 (9)0.0060 (11)0.0067 (10)
C260.0487 (12)0.0366 (11)0.0413 (12)0.0025 (9)0.0064 (10)0.0038 (9)
N310.0465 (10)0.0316 (9)0.0516 (11)0.0020 (7)0.0038 (9)0.0004 (8)
C320.0403 (11)0.0278 (10)0.0416 (12)0.0011 (8)0.0085 (9)0.0011 (9)
C330.0489 (12)0.0347 (11)0.0465 (13)0.0044 (9)0.0096 (10)0.0045 (9)
C340.0501 (13)0.0454 (13)0.0577 (15)0.0101 (10)0.0020 (11)0.0098 (11)
C350.0508 (14)0.0544 (14)0.0619 (16)0.0010 (11)0.0128 (12)0.0085 (12)
C360.0556 (14)0.0451 (13)0.0603 (16)0.0066 (11)0.0108 (12)0.0005 (11)
C370.0767 (17)0.0264 (10)0.0609 (16)0.0073 (10)0.0055 (12)0.0030 (10)
N410.0599 (12)0.0434 (11)0.0673 (14)0.0075 (9)0.0014 (11)0.0071 (10)
C420.0479 (12)0.0352 (11)0.0479 (13)0.0031 (9)0.0132 (10)0.0027 (9)
C430.0458 (12)0.0402 (11)0.0463 (13)0.0041 (9)0.0168 (10)0.0030 (10)
C440.0547 (14)0.0569 (14)0.0517 (15)0.0106 (11)0.0124 (11)0.0066 (12)
C450.0531 (15)0.0798 (19)0.0560 (16)0.0043 (13)0.0016 (12)0.0030 (14)
C460.0638 (16)0.0644 (17)0.0720 (19)0.0140 (13)0.0044 (14)0.0117 (14)
C470.0588 (14)0.0311 (11)0.0658 (16)0.0044 (10)0.0197 (12)0.0041 (11)
N510.0591 (12)0.0361 (10)0.0745 (15)0.0017 (9)0.0093 (11)0.0089 (10)
C520.0454 (12)0.0343 (11)0.0525 (14)0.0013 (9)0.0128 (10)0.0030 (10)
C530.0424 (12)0.0418 (12)0.0523 (14)0.0049 (9)0.0115 (10)0.0008 (10)
C540.0468 (13)0.0615 (15)0.0642 (17)0.0138 (11)0.0056 (12)0.0003 (13)
C550.0476 (14)0.0744 (18)0.081 (2)0.0006 (13)0.0023 (13)0.0232 (15)
C560.0624 (16)0.0514 (15)0.092 (2)0.0076 (12)0.0096 (15)0.0245 (14)
C570.0571 (14)0.0364 (12)0.0631 (16)0.0073 (10)0.0136 (12)0.0077 (11)
Geometric parameters (Å, º) top
O14—C141.352 (2)C33—C341.401 (3)
S1—C111.755 (2)C33—C371.431 (3)
S1—O111.4417 (15)C34—C351.350 (3)
O24—C241.350 (3)C35—C361.392 (3)
S1—C211.750 (2)C37—C37i1.337 (5)
S1—O121.4433 (15)N41—C421.352 (3)
C11—C121.386 (3)N41—C461.317 (3)
C11—C161.381 (3)C42—C431.412 (3)
C12—C131.379 (3)C42—C521.446 (3)
C13—C141.385 (3)C43—C441.405 (3)
C14—C151.389 (3)C43—C471.426 (3)
C15—C161.379 (3)C44—C451.349 (3)
C21—C221.386 (3)C45—C461.392 (3)
C21—C261.385 (3)C47—C571.340 (3)
C22—C231.373 (3)N51—C521.354 (3)
C23—C241.386 (3)N51—C561.321 (3)
C24—C251.378 (3)C52—C531.404 (3)
C25—C261.378 (3)C53—C541.399 (3)
N31—C321.357 (2)C53—C571.431 (3)
N31—C361.325 (3)C54—C551.355 (3)
C32—C32i1.448 (4)C55—C561.395 (4)
C32—C331.411 (3)
C11—S1—C21106.51 (9)C32—C33—C34118.13 (19)
O14—C14—C13122.51 (18)C32—C33—C37119.95 (19)
O14—C14—C15117.73 (19)C34—C33—C37121.90 (19)
O11—S1—O12117.75 (10)C33—C34—C35119.7 (2)
O24—C24—C23116.2 (2)C34—C35—C36118.6 (2)
O24—C24—C25123.7 (2)N31—C36—C35124.3 (2)
O11—S1—C11107.07 (9)C37i—C37—C33121.05 (12)
O11—S1—C21108.65 (10)C42—N41—C46117.3 (2)
O12—S1—C11108.35 (9)N41—C42—C43122.2 (2)
O12—S1—C21107.98 (9)N41—C42—C52118.58 (18)
S1—C11—C12119.27 (15)C43—C42—C52119.25 (18)
S1—C11—C16120.53 (15)C42—C43—C44117.6 (2)
C12—C11—C16120.02 (18)C42—C43—C47119.4 (2)
C11—C12—C13120.00 (18)C44—C43—C47123.0 (2)
C12—C13—C14120.01 (18)C43—C44—C45119.9 (2)
C13—C14—C15119.73 (18)C44—C45—C46118.1 (2)
C14—C15—C16120.1 (2)N41—C46—C45124.9 (2)
C11—C16—C15120.00 (19)C43—C47—C57121.5 (2)
S1—C21—C22119.36 (15)C52—N51—C56117.1 (2)
S1—C21—C26120.83 (16)N51—C52—C42118.07 (19)
C22—C21—C26119.78 (19)N51—C52—C53122.8 (2)
C21—C22—C23119.79 (19)C42—C52—C53119.11 (18)
C22—C23—C24120.3 (2)C52—C53—C54117.6 (2)
C23—C24—C25120.1 (2)C52—C53—C57119.8 (2)
C24—C25—C26119.74 (19)C54—C53—C57122.5 (2)
C21—C26—C25120.3 (2)C53—C54—C55119.6 (2)
C32—N31—C36117.49 (18)C54—C55—C56118.7 (2)
N31—C32—C32i119.43 (11)N51—C56—C55124.1 (2)
N31—C32—C33121.69 (18)C47—C57—C53120.9 (2)
C33—C32—C32i118.87 (12)
O11—S1—C11—C122.0 (2)C32—C33—C34—C351.7 (3)
C11—S1—C21—C2267.3 (2)C37—C33—C34—C35176.4 (2)
C11—S1—C21—C26114.8 (2)C33—C34—C35—C361.3 (4)
O12—S1—C21—C261.4 (2)C32—N31—C36—C351.4 (4)
C21—S1—C11—C12118.1 (2)C34—C35—C36—N313.1 (4)
C21—S1—C11—C1666.7 (2)C34—C33—C37—C37i177.1 (3)
O11—S1—C11—C16177.22 (16)C32—C33—C37—C37i0.9 (4)
O12—S1—C11—C1649.27 (18)C46—N41—C42—C430.9 (3)
O12—S1—C11—C12125.93 (16)C46—N41—C42—C52179.1 (2)
C16—C11—C12—C132.3 (3)N41—C42—C43—C442.2 (3)
S1—C11—C12—C13172.89 (15)C52—C42—C43—C44179.6 (2)
C11—C12—C13—C141.3 (3)N41—C42—C43—C47177.5 (2)
C12—C13—C14—O14177.87 (19)C52—C42—C43—C470.7 (3)
C12—C13—C14—C154.1 (3)C42—C43—C44—C452.2 (3)
O14—C14—C15—C16178.52 (19)C47—C43—C44—C45177.4 (2)
C13—C14—C15—C163.4 (3)C43—C44—C45—C461.0 (4)
C14—C15—C16—C110.2 (3)C42—N41—C46—C450.5 (4)
C12—C11—C16—C153.1 (3)C44—C45—C46—N410.4 (4)
S1—C11—C16—C15172.08 (16)C44—C43—C47—C57179.4 (2)
O11—S1—C21—C26130.19 (17)C42—C43—C47—C570.2 (3)
O11—S1—C21—C2247.77 (19)C56—N51—C52—C531.2 (3)
O12—S1—C21—C22176.53 (17)C56—N51—C52—C42178.2 (2)
C26—C21—C22—C231.4 (3)N41—C42—C52—N512.8 (3)
S1—C21—C22—C23176.53 (18)C43—C42—C52—N51179.00 (19)
C21—C22—C23—C240.1 (4)N41—C42—C52—C53176.7 (2)
C22—C23—C24—O24180.0 (2)C43—C42—C52—C531.6 (3)
C22—C23—C24—C250.8 (4)N51—C52—C53—C541.6 (3)
O24—C24—C25—C26179.6 (2)C42—C52—C53—C54177.8 (2)
C23—C24—C25—C260.3 (3)N51—C52—C53—C57179.0 (2)
C24—C25—C26—C211.0 (3)C42—C52—C53—C571.6 (3)
C22—C21—C26—C251.9 (3)C52—C53—C54—C550.7 (3)
S1—C21—C26—C25176.08 (16)C57—C53—C54—C55179.9 (2)
C36—N31—C32—C331.8 (3)C53—C54—C55—C560.3 (4)
C36—N31—C32—C32i179.7 (2)C52—N51—C56—C550.1 (4)
N31—C32—C33—C343.4 (3)C54—C55—C56—N510.7 (4)
C32i—C32—C33—C34178.1 (2)C43—C47—C57—C530.3 (4)
N31—C32—C33—C37174.8 (2)C54—C53—C57—C47178.7 (2)
C32i—C32—C33—C373.7 (4)C52—C53—C57—C470.6 (3)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N310.822.052.861 (2)171
O24—H24···N410.822.122.896 (2)159
O24—H24···N510.822.483.015 (3)124
C12—H12···O110.932.472.861 (3)106
C15—H15···O12ii0.932.553.406 (3)153
C26—H26···O120.932.532.911 (3)105
Symmetry code: (ii) x+1, y+1, z.
(4) 1,1,1-Tris(4-hydroxyphenyl)ethane–1,10-phenanthroline–methanol (1/1/1) top
Crystal data top
C20H18O3·C12H8N2·CH4O? #Insert any comments here.
Mr = 518.59Dx = 1.270 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 22.811 (3) Åθ = 9.9–15.7°
b = 22.029 (3) ŵ = 0.08 mm1
c = 10.7965 (10) ÅT = 294 K
V = 5425.3 (12) Å3Plate, colorless
Z = 80.42 × 0.42 × 0.14 mm
F(000) = 2192
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.008
Radiation source: X-ray tubeθmax = 25.2°, θmin = 2.0°
Graphite monochromatorh = 027
θ/2θ scansk = 026
5200 measured reflectionsl = 012
4861 independent reflections3 standard reflections every 120 min
2178 reflections with I > 2σ(I) intensity decay: 1.6%
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.108Calculated w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
4861 reflectionsΔρmax = 0.16 e Å3
358 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (3)
Crystal data top
C20H18O3·C12H8N2·CH4OV = 5425.3 (12) Å3
Mr = 518.59Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 22.811 (3) ŵ = 0.08 mm1
b = 22.029 (3) ÅT = 294 K
c = 10.7965 (10) Å0.42 × 0.42 × 0.14 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.008
5200 measured reflections3 standard reflections every 120 min
4861 independent reflections intensity decay: 1.6%
2178 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 0.87Δρmax = 0.16 e Å3
4861 reflectionsΔρmin = 0.14 e Å3
358 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Mean plane data ex last SHELXL run

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.7510 (0.0630) x + 5.6997 (0.0266) y + 10.4228 (0.0040) z = 5.5646 (0.0090)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C11

Rms deviation of fitted atoms = 0.0000

- 15.8689 (0.0101) x + 7.8947 (0.0125) y - 6.7217 (0.0072) z = 0.6987 (0.0060)

Angle to previous plane (with approximate e.s.d.) = 60.96 (13)

* 0.0067 (0.0013) C1 * -0.0019 (0.0016) C11 * -0.0018 (0.0015) C12 * -0.0030 (0.0016) C13 * -0.0048 (0.0019) C14 * 0.0102 (0.0015) O14 * -0.0052 (0.0017) C15 * -0.0003 (0.0016) C16

Rms deviation of fitted atoms = 0.0052

- 16.4518 (0.0182) x - 8.6530 (0.0500) y + 6.1601 (0.0157) z = 4.4005 (0.0122)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C21

Rms deviation of fitted atoms = 0.0000

- 19.2700 (0.0055) x + 3.8554 (0.0178) y + 5.4598 (0.0042) z = 6.2178 (0.0016)

Angle to previous plane (with approximate e.s.d.) = 34.00 (10)

* 0.0004 (0.0013) C1 * -0.0092 (0.0016) C21 * 0.0030 (0.0015) C22 * 0.0045 (0.0016) C23 * -0.0044 (0.0017) C24 * -0.0016 (0.0013) O24 * 0.0020 (0.0015) C25 * 0.0054 (0.0016) C26

Rms deviation of fitted atoms = 0.0046

15.3348 (0.0187) x + 13.9865 (0.0335) y + 4.1106 (0.0242) z = 1.1091 (0.0106)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C31

Rms deviation of fitted atoms = 0.0000

6.6356 (0.0169) x + 21.0757 (0.0059) y + 0.0834 (0.0072) z = 1.7333 (0.0037)

Angle to previous plane (with approximate e.s.d.) = 36.30 (13)

* -0.0258 (0.0013) C1 * -0.0158 (0.0016) C31 * 0.0114 (0.0017) C32 * 0.0274 (0.0017) C33 * 0.0042 (0.0018) C34 * -0.0432 (0.0014) O34 * 0.0237 (0.0018) C35 * 0.0181 (0.0018) C36

Rms deviation of fitted atoms = 0.0239

13.1477 (0.0061) x + 13.8758 (0.0079) y - 5.6207 (0.0046) z = 2.4056 (0.0060)

* -0.0078 (0.0017) N41 * -0.0214 (0.0021) C42 * -0.0141 (0.0026) C43 * 0.0072 (0.0026) C44 * 0.0100 (0.0022) C45 * 0.0189 (0.0024) C46 * -0.0041 (0.0025) C47 * -0.0056 (0.0022) C48 * -0.0277 (0.0026) C49 * -0.0188 (0.0027) C410 * 0.0156 (0.0021) C411 * 0.0294 (0.0017) N412 * 0.0111 (0.0019) C413 * 0.0073 (0.0019) C414

Rms deviation of fitted atoms = 0.0162

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.16889 (7)0.13242 (8)0.44931 (19)0.0420 (5)
C20.12824 (9)0.07829 (9)0.4818 (2)0.0595 (6)
C110.12945 (7)0.18741 (8)0.42207 (19)0.0402 (5)
C120.13105 (8)0.24074 (9)0.48848 (19)0.0471 (5)
C130.09496 (9)0.28919 (9)0.4603 (2)0.0514 (5)
C140.05624 (9)0.28508 (9)0.3644 (2)0.0526 (6)
O140.01994 (9)0.33235 (8)0.33196 (16)0.0879 (6)
C150.05346 (9)0.23247 (10)0.2961 (2)0.0583 (6)
C160.08960 (9)0.18476 (9)0.3246 (2)0.0533 (6)
C210.20458 (8)0.11707 (8)0.33243 (19)0.0420 (5)
C220.22405 (9)0.05840 (9)0.3074 (2)0.0521 (6)
C230.25645 (9)0.04520 (10)0.2026 (2)0.0574 (6)
C240.27059 (8)0.09013 (10)0.1193 (2)0.0506 (6)
O240.30283 (7)0.07455 (7)0.01706 (14)0.0709 (5)
C250.25273 (8)0.14858 (9)0.14228 (19)0.0513 (5)
C260.22046 (9)0.16144 (9)0.2477 (2)0.0491 (5)
C310.21001 (8)0.14540 (8)0.55852 (19)0.0425 (5)
C320.26691 (8)0.16467 (10)0.5431 (2)0.0558 (6)
C330.30353 (9)0.17657 (10)0.6424 (2)0.0591 (6)
C340.28382 (9)0.16879 (9)0.7608 (2)0.0510 (6)
O340.31872 (6)0.17712 (8)0.86381 (14)0.0723 (5)
C350.22688 (9)0.15172 (11)0.7795 (2)0.0665 (7)
C360.19098 (9)0.14054 (10)0.6794 (2)0.0630 (7)
N410.02443 (9)0.37652 (10)0.56006 (19)0.0681 (6)
C420.07088 (13)0.34605 (14)0.5959 (3)0.0935 (9)
C430.10249 (14)0.3596 (2)0.7021 (4)0.1140 (13)
C440.08533 (15)0.4065 (2)0.7739 (3)0.1087 (12)
C450.03554 (13)0.44034 (14)0.7404 (3)0.0792 (8)
C460.01375 (17)0.49021 (17)0.8110 (3)0.1045 (12)
C470.03415 (19)0.51962 (15)0.7756 (4)0.1081 (12)
C480.06523 (14)0.50418 (12)0.6651 (3)0.0791 (8)
C490.11577 (18)0.53446 (14)0.6256 (4)0.1081 (12)
C4100.14212 (15)0.51726 (19)0.5199 (5)0.1152 (14)
C4110.11815 (14)0.47019 (15)0.4536 (3)0.0954 (10)
N4120.07091 (9)0.43950 (9)0.4859 (2)0.0711 (6)
C4130.04475 (10)0.45656 (10)0.5925 (2)0.0591 (6)
C4140.00641 (10)0.42342 (11)0.6310 (2)0.0590 (6)
O510.06663 (7)0.31812 (10)0.16278 (16)0.0862 (6)
C510.03656 (12)0.32226 (14)0.0494 (3)0.0935 (9)
H2A0.10150.09020.54600.089*
H2B0.10660.06640.40960.089*
H2C0.15150.04470.51010.089*
H120.15720.24430.55420.057*
H130.09710.32460.50690.062*
H140.01590.35520.39130.132*
H150.02710.22930.23070.070*
H160.08740.14950.27740.064*
H220.21500.02730.36250.062*
H230.26880.00560.18830.069*
H240.31130.10530.02190.106*
H250.26230.17950.08710.062*
H260.20900.20130.26230.059*
H320.28130.16990.46320.067*
H330.34170.18990.62850.071*
H340.35300.18040.84220.108*
H350.21240.14760.85960.080*
H360.15230.12930.69390.076*
H420.08330.31360.54750.112*
H430.13520.33670.72350.137*
H440.10630.41640.84500.130*
H460.03330.50220.88250.125*
H470.04800.55130.82440.130*
H490.13100.56630.67210.130*
H4100.17580.53680.49230.138*
H4110.13670.45910.38030.114*
H510.04310.32060.22010.129*
H51A0.05760.30000.01300.130*0.50
H51B0.00200.30550.05820.130*0.50
H51C0.03360.36400.02490.130*0.50
H51D0.02580.28230.02180.130*0.50
H51E0.00190.34630.05970.130*0.50
H51F0.06150.34080.01150.130*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0434 (11)0.0421 (11)0.0405 (13)0.0008 (9)0.0022 (10)0.0013 (10)
C20.0634 (13)0.0551 (13)0.0601 (17)0.0066 (11)0.0050 (12)0.0053 (12)
C110.0398 (11)0.0459 (11)0.0348 (13)0.0001 (9)0.0002 (10)0.0000 (10)
C120.0490 (11)0.0558 (13)0.0365 (13)0.0018 (10)0.0088 (10)0.0021 (11)
C130.0619 (13)0.0483 (12)0.0438 (14)0.0100 (11)0.0080 (12)0.0058 (11)
C140.0575 (13)0.0612 (14)0.0391 (14)0.0198 (11)0.0062 (12)0.0030 (12)
O140.1103 (13)0.0897 (12)0.0636 (13)0.0553 (10)0.0359 (11)0.0190 (10)
C150.0549 (13)0.0776 (16)0.0425 (14)0.0150 (11)0.0172 (11)0.0090 (13)
C160.0544 (12)0.0571 (13)0.0483 (15)0.0084 (11)0.0129 (12)0.0130 (11)
C210.0467 (11)0.0419 (11)0.0376 (13)0.0009 (9)0.0056 (10)0.0008 (11)
C220.0630 (13)0.0441 (12)0.0491 (15)0.0061 (10)0.0011 (12)0.0030 (11)
C230.0665 (14)0.0485 (13)0.0572 (16)0.0142 (11)0.0021 (13)0.0060 (12)
C240.0539 (13)0.0614 (14)0.0366 (14)0.0117 (11)0.0041 (11)0.0098 (12)
O240.0859 (11)0.0816 (11)0.0453 (11)0.0203 (10)0.0076 (9)0.0106 (9)
C250.0622 (13)0.0547 (13)0.0370 (13)0.0078 (11)0.0013 (12)0.0035 (11)
C260.0591 (13)0.0440 (12)0.0442 (14)0.0097 (10)0.0001 (11)0.0031 (11)
C310.0433 (11)0.0473 (12)0.0368 (14)0.0051 (9)0.0003 (10)0.0059 (10)
C320.0545 (13)0.0795 (15)0.0335 (13)0.0103 (11)0.0033 (11)0.0045 (12)
C330.0487 (12)0.0856 (16)0.0429 (15)0.0137 (11)0.0037 (12)0.0004 (13)
C340.0479 (13)0.0663 (14)0.0388 (15)0.0057 (11)0.0026 (11)0.0001 (12)
O340.0544 (9)0.1226 (13)0.0398 (10)0.0026 (10)0.0050 (8)0.0052 (9)
C350.0514 (13)0.115 (2)0.0334 (14)0.0043 (13)0.0048 (12)0.0093 (14)
C360.0424 (12)0.1016 (19)0.0449 (16)0.0021 (12)0.0022 (12)0.0135 (14)
N410.0611 (12)0.0741 (13)0.0691 (15)0.0114 (10)0.0048 (12)0.0067 (13)
C420.0723 (18)0.105 (2)0.104 (3)0.0053 (18)0.016 (2)0.020 (2)
C430.069 (2)0.159 (4)0.114 (3)0.009 (2)0.002 (2)0.056 (3)
C440.078 (2)0.175 (4)0.073 (3)0.048 (2)0.016 (2)0.038 (3)
C450.0784 (19)0.105 (2)0.0546 (19)0.0466 (17)0.0034 (16)0.0126 (18)
C460.134 (3)0.121 (3)0.058 (2)0.071 (2)0.007 (2)0.017 (2)
C470.150 (3)0.082 (2)0.093 (3)0.045 (2)0.045 (3)0.023 (2)
C480.096 (2)0.0594 (16)0.082 (2)0.0229 (16)0.0248 (19)0.0002 (17)
C490.110 (3)0.070 (2)0.144 (4)0.006 (2)0.044 (3)0.021 (2)
C4100.085 (2)0.099 (3)0.162 (4)0.003 (2)0.013 (3)0.050 (3)
C4110.087 (2)0.089 (2)0.110 (3)0.0259 (18)0.022 (2)0.034 (2)
N4120.0746 (14)0.0687 (13)0.0700 (17)0.0213 (11)0.0152 (12)0.0103 (12)
C4130.0658 (15)0.0523 (14)0.0593 (17)0.0238 (12)0.0076 (14)0.0080 (14)
C4140.0629 (15)0.0635 (14)0.0505 (16)0.0288 (13)0.0021 (13)0.0051 (13)
O510.0582 (9)0.1455 (16)0.0548 (12)0.0236 (11)0.0002 (9)0.0008 (12)
C510.097 (2)0.124 (2)0.060 (2)0.0228 (17)0.0107 (17)0.0039 (17)
Geometric parameters (Å, º) top
C14—O141.376 (2)C32—C331.385 (3)
C34—O341.380 (2)C33—C341.365 (3)
C1—C21.551 (2)C34—C351.367 (3)
C1—C111.537 (2)C35—C361.378 (3)
C1—C211.539 (3)N41—C421.313 (3)
C1—C311.534 (3)N41—C4141.350 (3)
C11—C121.377 (3)C42—C431.387 (4)
C11—C161.392 (3)C43—C441.350 (5)
C12—C131.382 (3)C44—C451.405 (4)
C13—C141.365 (3)C45—C4141.406 (3)
C14—C151.375 (3)C45—C461.426 (4)
C15—C161.371 (3)C46—C471.326 (4)
C21—C221.393 (3)C47—C481.429 (4)
C21—C261.387 (3)C48—C491.399 (4)
C22—C231.382 (3)C48—C4131.391 (3)
C23—C241.376 (3)C49—C4101.344 (4)
C24—O241.370 (2)C410—C4111.373 (4)
C24—C251.373 (3)C411—N4121.319 (3)
C25—C261.385 (3)N412—C4131.350 (3)
C31—C321.376 (3)C413—C4141.438 (3)
C31—C361.379 (3)O51—C511.406 (3)
C13—C14—O14122.2 (2)C1—C31—C36121.36 (17)
C23—C24—O24118.2 (2)C32—C31—C36115.8 (2)
C33—C34—O34123.2 (2)C31—C32—C33122.3 (2)
O14—C14—C15118.3 (2)C32—C33—C34120.17 (19)
O24—C24—C25122.6 (2)C33—C34—C35119.0 (2)
O34—C34—C35117.7 (2)C35—C36—C31122.75 (19)
C2—C1—C11107.42 (14)C34—C35—C36119.9 (2)
C2—C1—C21109.45 (16)C42—N41—C414118.0 (3)
C2—C1—C31109.57 (16)N41—C42—C43123.6 (3)
C11—C1—C21109.02 (15)C42—C43—C44119.3 (3)
C11—C1—C31110.97 (15)C43—C44—C45119.5 (3)
C1—C11—C12123.87 (17)C44—C45—C46123.5 (3)
C1—C11—C16119.59 (17)C44—C45—C414117.2 (3)
C21—C1—C31110.35 (14)C46—C45—C414119.2 (3)
C12—C11—C16116.53 (17)C45—C46—C47120.6 (3)
C11—C12—C13121.93 (18)C46—C47—C48122.2 (3)
C12—C13—C14120.09 (19)C47—C48—C49123.4 (4)
C13—C14—C15119.53 (18)C47—C48—C413118.9 (3)
C14—C15—C16119.86 (19)C49—C48—C413117.7 (3)
C11—C16—C15122.06 (19)C48—C49—C410119.6 (4)
C1—C21—C22122.12 (18)C49—C410—C411118.5 (4)
C1—C21—C26121.60 (16)N412—C411—C410125.1 (3)
C22—C21—C26116.26 (19)C411—N412—C413116.3 (3)
C21—C22—C23121.7 (2)N412—C413—C48122.8 (3)
C22—C23—C24120.60 (19)N412—C413—C414117.7 (2)
C23—C24—C25119.2 (2)C48—C413—C414119.5 (3)
C24—C25—C26119.9 (2)N41—C414—C45122.4 (3)
C21—C26—C25122.46 (18)N41—C414—C413118.1 (2)
C1—C31—C32122.78 (19)C45—C414—C413119.5 (3)
C2—C1—C11—C12119.3 (2)C31—C32—C33—C340.6 (3)
C2—C1—C21—C2234.8 (2)C32—C33—C34—C352.8 (3)
C2—C1—C31—C32144.8 (2)C32—C33—C34—O34177.0 (2)
C2—C1—C11—C1661.2 (2)C32—C31—C36—C352.6 (3)
C2—C1—C21—C26146.9 (2)C1—C31—C36—C35179.80 (19)
C2—C1—C31—C3637.7 (2)C33—C34—C35—C362.3 (3)
C31—C1—C11—C120.5 (2)O34—C34—C35—C36177.5 (2)
C21—C1—C11—C12122.2 (2)C31—C36—C35—C340.4 (4)
C31—C1—C11—C16179.03 (17)C414—N41—C42—C430.3 (4)
C21—C1—C11—C1657.3 (2)N41—C42—C43—C440.0 (5)
C16—C11—C12—C130.1 (3)C42—C43—C44—C450.5 (5)
C1—C11—C12—C13179.67 (17)C43—C44—C45—C4140.8 (4)
C11—C12—C13—C140.0 (3)C43—C44—C45—C46179.4 (3)
C12—C13—C14—C150.0 (3)C44—C45—C46—C47178.7 (3)
C12—C13—C14—O14179.2 (2)C414—C45—C46—C471.4 (4)
C13—C14—C15—C160.2 (3)C45—C46—C47—C481.6 (5)
O14—C14—C15—C16179.1 (2)C46—C47—C48—C4130.3 (4)
C14—C15—C16—C110.3 (3)C46—C47—C48—C49179.9 (3)
C12—C11—C16—C150.3 (3)C413—C48—C49—C4100.6 (4)
C1—C11—C16—C15179.88 (19)C47—C48—C49—C410179.6 (3)
C31—C1—C21—C2692.4 (2)C48—C49—C410—C4110.2 (5)
C11—C1—C21—C2629.7 (2)C49—C410—C411—N4120.6 (5)
C31—C1—C21—C2285.8 (2)C410—C411—N412—C4130.2 (4)
C11—C1—C21—C22152.04 (17)C411—N412—C413—C480.7 (3)
C26—C21—C22—C231.2 (3)C411—N412—C413—C414179.18 (19)
C1—C21—C22—C23179.50 (18)C49—C48—C413—N4121.1 (3)
C21—C22—C23—C240.1 (3)C47—C48—C413—N412179.1 (2)
C22—C23—C24—O24179.96 (18)C49—C48—C413—C414178.8 (2)
C22—C23—C24—C250.8 (3)C47—C48—C413—C4141.0 (3)
O24—C24—C25—C26179.68 (19)C42—N41—C414—C450.1 (3)
C23—C24—C25—C260.6 (3)C42—N41—C414—C413179.5 (2)
C24—C25—C26—C210.6 (3)C44—C45—C414—N410.5 (3)
C22—C21—C26—C251.4 (3)C46—C45—C414—N41179.7 (2)
C1—C21—C26—C25179.76 (18)C44—C45—C414—C413179.9 (2)
C11—C1—C31—C3296.7 (2)C46—C45—C414—C4130.1 (3)
C21—C1—C31—C3224.2 (2)N412—C413—C414—N411.4 (3)
C11—C1—C31—C3680.7 (2)C48—C413—C414—N41178.47 (19)
C21—C1—C31—C36158.30 (19)N412—C413—C414—C45178.99 (19)
C36—C31—C32—C332.0 (3)C48—C413—C414—C451.1 (3)
C1—C31—C32—C33179.64 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···N410.822.092.835 (3)150
O14—H14···N4120.822.463.112 (3)137
O24—H24···O34i0.822.012.824 (2)169
O34—H34···O51ii0.821.832.633 (2)165
O51—H51···O140.821.902.708 (3)170
C13—H13···N4120.932.613.368 (3)139
C44—H44···O24iii0.932.563.432 (4)156
Symmetry codes: (i) x, y, z1; (ii) x1/2, y+1/2, z+1; (iii) x+1/2, y+1/2, z+1.

Experimental details

(1)(2)(3)(4)
Crystal data
Chemical formulaC12H10O2·C12H8N2C12H10O2S·2(C12H8N2)2(C12H10O4S)·3(C12H8N2)C20H18O3·C12H8N2·CH4O
Mr366.40578.691041.13518.59
Crystal system, space groupMonoclinic, C2/cTriclinic, P1Monoclinic, C2/cOrthorhombic, Pbca
Temperature (K)294294294294
a, b, c (Å)13.0288 (17), 12.1865 (10), 12.0778 (12)7.7342 (5), 13.3624 (14), 14.9843 (11)15.8692 (16), 24.3728 (17), 13.0952 (9)22.811 (3), 22.029 (3), 10.7965 (10)
α, β, γ (°)90, 105.199 (9), 90110.514 (6), 95.195 (6), 95.895 (7)90, 102.362 (8), 9090, 90, 90
V3)1850.6 (3)1429.3 (2)4947.5 (7)5425.3 (12)
Z4248
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.160.180.08
Crystal size (mm)0.42 × 0.31 × 0.120.42 × 0.35 × 0.220.42 × 0.38 × 0.100.42 × 0.42 × 0.14
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionGaussian
ABSORB in NRCVAX (Gabe et al., 1989)
Gaussian
ABSORB in NRCVAX (Gabe et al., 1989)
Tmin, Tmax0.946, 0.9700.937, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
1748, 1678, 915 5184, 5184, 3431 4636, 4434, 3182 5200, 4861, 2178
Rint0.0120.0000.0060.008
(sin θ/λ)max1)0.5990.5990.5980.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.099, 0.98 0.035, 0.100, 1.04 0.041, 0.104, 1.03 0.039, 0.108, 0.87
No. of reflections1678518444344861
No. of parameters129391346358
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.130.20, 0.200.22, 0.300.16, 0.14

Computer programs: CAD4 (Enraf-Nonius, 1992), SET4 & CELDIM (Enraf-Nonius, 1992), DATRD2 in NRCVAX96 (Gabe et al., 1989), DATRD2 in NRCVAX96 (Gabe et al., 1989 1989), SHELXS97 (Sheldrick, 1997a), NRCVAX96 and SHELXL97 (Sheldrick, 1997b), NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998), NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997).

(1)
O14···N12.878 (2)O14—H14···N1159
C12···O14i3.403 (2)C12—H12···O14i148
(2)
O14···N312.741 (2)O14—H14···N31153
O24···N512.757 (2)O24—H24···N51151
(3)
O14···N312.861 (2)O14—H14···N31171
O24···N412.896 (2)O24—H24···N41159
O24···N513.015 (3)O24—H24···N51124
C15···O12ii3.406 (3)C15—H15···O12ii153
(4)
O51···O142.708 (3)O51—H51···O14170
O24···O34iii2.824 (2)O24—H24···O34iii169
O34···O51iv2.633 (2)O34—H34···O51iv165
O14···N412.835 (3)O14—H14···N41150
O14···N4123.112 (3)O14—H14···N412137
C44···O24v3.432 (4)C44—H44···O24v156
(i) x, 1-y, -1/2+z; (ii) 1-x, 1-y, -z; (iii) x, y, -1+z; (iv) -1/2+x, 1/2-y, 1-z; (v) 1/2+x, 1/2-y, 1-z.
 
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