Two new polymorphs of cis-perinone: crystal structures, physical and electric properties

The crystal structures of two polymorphs of cis-perinone (bis­benzimidazo[2,1-b:1′,2′-j]benzo[lmn][3,8]phenanthroline-6,9-dione, Pigment Red 194) were solved from single crystals obtained solvothermally from 1,2-di­chloro­benzene or n-butanol at 220°C. Both crystal structures (space group P2₁/c) derive from stacking of flat molecules arranged due to π–π interaction. The melting points of these two polymorphs are 471°C and 468°C and their respective optical bandgaps are 1.94 eV and 1.71 eV. One of the polymorphs demonstrates drift and hopping mechanisms of electric conductivity, whereas the other one is dominated by the drift conductivity. The direct current (DC) electric conductivity of the samples are 4.77 × 10⁻¹³ S m⁻¹ and 6.84 × 10⁻¹⁰ S m⁻¹ at room temperature. The significant difference in DC conductivities can be explained by the dependence of the mobility and concentration of charge carriers on the structure of the samples.

Computing details

Data collection: APEX II v.2013.6-2, (Bruker, 2013) for polymorph1. Cell refinement: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Data reduction: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Program(s) used to solve structure: SHELXT-2014/4 (Sheldrick, 2014) for polymorph1; SHELXS97 (Sheldrick, 1990) for polymorph2. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for polymorph1; SHELXL97 (Sheldrick, 1997) for polymorph2. Molecular graphics: Bruker SHELXTL (Bruker AXS Inc., 2013) for polymorph1.

bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione (polymorph1)

Crystal data

C26H12N4O2	Dx = 1.604 Mg m^−3
Mr = 412.40	Melting point: 744 K
Monoclinic, P21/c	Synchrotron radiation, λ = 0.41328 Å
a = 13.1190 (8) Å	Cell parameters from 5223 reflections
b = 4.7770 (3) Å	θ = 2.4–17.4°
c = 27.3921 (17) Å	µ = 0.03 mm^−1
β = 95.8533 (12)°	T = 100 K
V = 1707.70 (18) Å^3	Plate, red
Z = 4	0.05 × 0.02 × 0.01 mm
F(000) = 848

Data collection

Bruker APEX II CCD diffractometer	3679 reflections with I > 2σ(I)
Radiation source: Advanced photon source	Rint = 0.075
Diamond (111) monochromator	θmax = 17.7°, θmin = 0.9°
φ–scan	h = −19→19
26791 measured reflections	k = −6→4
5376 independent reflections	l = −39→40

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.203	w = 1/[σ^2(Fo^2) + (0.1151P)^2 + 0.2566P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
5376 reflections	Δρmax = 0.66 e Å^−3
289 parameters	Δρmin = −0.32 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.54706 (10)	−0.1783 (3)	0.45993 (5)	0.0297 (3)
O2	0.56344 (10)	0.8576 (3)	0.27759 (5)	0.0286 (3)
N1	0.70844 (11)	−0.0567 (3)	0.49048 (5)	0.0212 (3)
N2	0.86812 (11)	0.0372 (3)	0.52634 (5)	0.0229 (3)
N3	0.72829 (11)	0.9507 (3)	0.30653 (5)	0.0191 (3)
N4	0.89346 (11)	1.0686 (3)	0.32888 (5)	0.0215 (3)
C1	0.62860 (13)	0.1885 (3)	0.41937 (6)	0.0209 (3)
C2	0.71995 (13)	0.3459 (3)	0.41729 (6)	0.0186 (3)
C3	0.80751 (13)	0.2996 (3)	0.45135 (6)	0.0199 (3)
C4	0.89671 (14)	0.4462 (4)	0.44682 (6)	0.0218 (3)
H4B	0.9559	0.4093	0.4689	0.026*
C5	0.90112 (13)	0.6486 (4)	0.41013 (6)	0.0218 (3)
H5A	0.9628	0.7499	0.4079	0.026*
C6	0.81646 (13)	0.7023 (3)	0.37711 (6)	0.0191 (3)
C7	0.72450 (13)	0.5485 (3)	0.38001 (6)	0.0184 (3)
C8	0.63626 (13)	0.5911 (4)	0.34588 (6)	0.0208 (3)
C9	0.54899 (13)	0.4329 (4)	0.34854 (7)	0.0244 (4)
H9A	0.4911	0.4610	0.3252	0.029*
C10	0.54526 (14)	0.2317 (4)	0.38528 (7)	0.0242 (4)
H10A	0.4849	0.1237	0.3868	0.029*
C11	0.62146 (13)	−0.0307 (4)	0.45749 (6)	0.0229 (4)
C12	0.72339 (14)	−0.2321 (4)	0.53177 (6)	0.0228 (4)
C13	0.66126 (15)	−0.4327 (4)	0.55088 (7)	0.0266 (4)
H13A	0.5945	−0.4743	0.5359	0.032*
C14	0.70286 (16)	−0.5680 (4)	0.59313 (7)	0.0288 (4)
H14A	0.6638	−0.7079	0.6074	0.035*
C15	0.80114 (16)	−0.5032 (4)	0.61524 (7)	0.0298 (4)
H15A	0.8266	−0.5993	0.6443	0.036*
C16	0.86218 (16)	−0.3031 (4)	0.59594 (7)	0.0269 (4)
H16A	0.9286	−0.2599	0.6112	0.032*
C17	0.82195 (14)	−0.1685 (4)	0.55339 (6)	0.0239 (4)
C18	0.79938 (13)	0.0971 (4)	0.49012 (6)	0.0202 (3)
C19	0.63632 (13)	0.8050 (3)	0.30698 (6)	0.0218 (3)
C20	0.75207 (13)	1.1609 (3)	0.27367 (6)	0.0199 (3)
C21	0.69356 (14)	1.2934 (4)	0.23530 (6)	0.0243 (4)
H21A	0.6235	1.2484	0.2267	0.029*
C22	0.74393 (14)	1.4964 (4)	0.21025 (7)	0.0247 (4)
H22A	0.7077	1.5918	0.1834	0.030*
C23	0.84649 (14)	1.5623 (4)	0.22376 (6)	0.0247 (4)
H23A	0.8787	1.6999	0.2055	0.030*
C24	0.90276 (14)	1.4335 (4)	0.26291 (7)	0.0247 (4)
H24A	0.9721	1.4834	0.2722	0.030*
C25	0.85440 (13)	1.2285 (4)	0.28826 (6)	0.0207 (3)
C26	0.81756 (12)	0.9084 (3)	0.33848 (6)	0.0191 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0280 (7)	0.0265 (7)	0.0351 (8)	−0.0075 (5)	0.0059 (6)	0.0011 (5)
O2	0.0232 (6)	0.0261 (7)	0.0345 (7)	−0.0015 (5)	−0.0070 (5)	0.0039 (5)
N1	0.0240 (7)	0.0181 (7)	0.0219 (7)	−0.0033 (5)	0.0043 (5)	−0.0012 (5)
N2	0.0287 (8)	0.0203 (7)	0.0197 (7)	−0.0003 (6)	0.0022 (6)	0.0000 (5)
N3	0.0205 (7)	0.0157 (7)	0.0207 (7)	0.0005 (5)	0.0003 (5)	−0.0004 (5)
N4	0.0233 (7)	0.0189 (7)	0.0224 (7)	−0.0009 (5)	0.0027 (5)	−0.0003 (5)
C1	0.0245 (8)	0.0147 (8)	0.0241 (8)	−0.0009 (6)	0.0046 (6)	−0.0035 (6)
C2	0.0234 (8)	0.0138 (7)	0.0188 (7)	0.0008 (6)	0.0026 (6)	−0.0023 (6)
C3	0.0242 (8)	0.0163 (8)	0.0194 (7)	0.0006 (6)	0.0037 (6)	−0.0016 (6)
C4	0.0254 (8)	0.0201 (8)	0.0194 (8)	−0.0002 (6)	0.0000 (6)	−0.0007 (6)
C5	0.0238 (8)	0.0191 (8)	0.0223 (8)	−0.0023 (6)	0.0015 (6)	−0.0014 (6)
C6	0.0228 (8)	0.0150 (8)	0.0197 (7)	0.0012 (6)	0.0030 (6)	−0.0029 (6)
C7	0.0219 (8)	0.0130 (7)	0.0204 (7)	0.0018 (6)	0.0028 (6)	−0.0019 (5)
C8	0.0245 (8)	0.0152 (8)	0.0225 (8)	0.0017 (6)	0.0019 (6)	−0.0018 (6)
C9	0.0213 (8)	0.0205 (9)	0.0307 (9)	0.0001 (6)	−0.0015 (7)	−0.0012 (7)
C10	0.0230 (8)	0.0196 (8)	0.0301 (9)	−0.0006 (6)	0.0026 (7)	−0.0022 (7)
C11	0.0245 (8)	0.0202 (8)	0.0245 (8)	−0.0012 (6)	0.0050 (7)	−0.0046 (6)
C12	0.0319 (9)	0.0170 (8)	0.0204 (8)	0.0023 (6)	0.0073 (7)	−0.0012 (6)
C13	0.0340 (10)	0.0216 (9)	0.0257 (9)	−0.0007 (7)	0.0092 (7)	−0.0010 (7)
C14	0.0411 (11)	0.0213 (9)	0.0256 (9)	−0.0013 (7)	0.0122 (8)	0.0009 (7)
C15	0.0422 (11)	0.0232 (9)	0.0250 (9)	0.0013 (8)	0.0080 (8)	0.0032 (7)
C16	0.0362 (10)	0.0227 (9)	0.0224 (8)	0.0013 (7)	0.0059 (7)	0.0010 (6)
C17	0.0309 (9)	0.0208 (8)	0.0208 (8)	0.0004 (7)	0.0059 (7)	−0.0017 (6)
C18	0.0240 (8)	0.0173 (8)	0.0193 (7)	−0.0007 (6)	0.0024 (6)	−0.0026 (6)
C19	0.0213 (8)	0.0167 (8)	0.0271 (9)	−0.0008 (6)	0.0009 (6)	−0.0035 (6)
C20	0.0246 (8)	0.0161 (8)	0.0191 (7)	0.0012 (6)	0.0024 (6)	−0.0020 (6)
C21	0.0259 (8)	0.0223 (9)	0.0239 (8)	0.0009 (6)	−0.0010 (6)	−0.0041 (6)
C22	0.0314 (9)	0.0195 (8)	0.0230 (8)	0.0007 (7)	0.0018 (7)	−0.0011 (6)
C23	0.0310 (9)	0.0200 (9)	0.0238 (8)	−0.0007 (7)	0.0057 (7)	0.0008 (6)
C24	0.0265 (9)	0.0208 (9)	0.0272 (9)	−0.0009 (6)	0.0047 (7)	0.0003 (6)
C25	0.0221 (8)	0.0174 (8)	0.0224 (8)	0.0006 (6)	0.0016 (6)	−0.0019 (6)
C26	0.0204 (8)	0.0160 (8)	0.0206 (7)	0.0011 (6)	0.0006 (6)	−0.0023 (6)

Geometric parameters (Å, º)

O1—C11	1.211 (2)	C8—C9	1.380 (2)
O2—C19	1.212 (2)	C8—C19	1.476 (2)
N1—C11	1.387 (2)	C9—C10	1.396 (3)
N1—C18	1.402 (2)	C9—H9A	0.9500
N1—C12	1.405 (2)	C10—H10A	0.9500
N2—C18	1.303 (2)	C12—C13	1.394 (2)
N2—C17	1.404 (2)	C12—C17	1.400 (3)
N3—C19	1.394 (2)	C13—C14	1.388 (3)
N3—C26	1.403 (2)	C13—H13A	0.9500
N3—C20	1.405 (2)	C14—C15	1.402 (3)
N4—C26	1.304 (2)	C14—H14A	0.9500
N4—C25	1.403 (2)	C15—C16	1.386 (3)
C1—C10	1.379 (2)	C15—H15A	0.9500
C1—C2	1.421 (2)	C16—C17	1.387 (3)
C1—C11	1.489 (2)	C16—H16A	0.9500
C2—C7	1.413 (2)	C20—C21	1.389 (2)
C2—C3	1.422 (2)	C20—C25	1.399 (2)
C3—C4	1.380 (2)	C21—C22	1.393 (3)
C3—C18	1.448 (2)	C21—H21A	0.9500
C4—C5	1.400 (2)	C22—C23	1.395 (3)
C4—H4B	0.9500	C22—H22A	0.9500
C5—C6	1.383 (2)	C23—C24	1.383 (3)
C5—H5A	0.9500	C23—H23A	0.9500
C6—C7	1.422 (2)	C24—C25	1.391 (2)
C6—C26	1.446 (2)	C24—H24A	0.9500
C7—C8	1.426 (2)
C11—N1—C18	126.34 (15)	C17—C12—N1	104.97 (15)
C11—N1—C12	128.01 (15)	C14—C13—C12	115.98 (18)
C18—N1—C12	105.62 (14)	C14—C13—H13A	122.0
C18—N2—C17	104.68 (14)	C12—C13—H13A	122.0
C19—N3—C26	126.20 (14)	C13—C14—C15	121.55 (18)
C19—N3—C20	127.70 (14)	C13—C14—H14A	119.2
C26—N3—C20	106.07 (13)	C15—C14—H14A	119.2
C26—N4—C25	104.76 (14)	C16—C15—C14	121.97 (18)
C10—C1—C2	120.49 (16)	C16—C15—H15A	119.0
C10—C1—C11	118.55 (15)	C14—C15—H15A	119.0
C2—C1—C11	120.94 (16)	C15—C16—C17	117.05 (18)
C7—C2—C1	119.31 (15)	C15—C16—H16A	121.5
C7—C2—C3	119.36 (15)	C17—C16—H16A	121.5
C1—C2—C3	121.31 (15)	C16—C17—C12	120.72 (17)
C4—C3—C2	119.85 (15)	C16—C17—N2	128.30 (17)
C4—C3—C18	122.10 (15)	C12—C17—N2	110.98 (15)
C2—C3—C18	118.05 (15)	N2—C18—N1	113.75 (15)
C3—C4—C5	120.83 (16)	N2—C18—C3	127.46 (16)
C3—C4—H4B	119.6	N1—C18—C3	118.78 (15)
C5—C4—H4B	119.6	O2—C19—N3	121.03 (16)
C6—C5—C4	120.56 (16)	O2—C19—C8	124.37 (16)
C6—C5—H5A	119.7	N3—C19—C8	114.59 (14)
C4—C5—H5A	119.7	C21—C20—C25	123.44 (16)
C5—C6—C7	119.81 (15)	C21—C20—N3	131.97 (16)
C5—C6—C26	122.51 (15)	C25—C20—N3	104.56 (14)
C7—C6—C26	117.68 (15)	C20—C21—C22	115.89 (17)
C2—C7—C6	119.54 (15)	C20—C21—H21A	122.1
C2—C7—C8	118.71 (15)	C22—C21—H21A	122.1
C6—C7—C8	121.75 (15)	C21—C22—C23	121.32 (17)
C9—C8—C7	120.62 (16)	C21—C22—H22A	119.3
C9—C8—C19	118.60 (15)	C23—C22—H22A	119.3
C7—C8—C19	120.78 (15)	C24—C23—C22	121.98 (17)
C8—C9—C10	120.36 (16)	C24—C23—H23A	119.0
C8—C9—H9A	119.8	C22—C23—H23A	119.0
C10—C9—H9A	119.8	C23—C24—C25	117.77 (17)
C1—C10—C9	120.49 (16)	C23—C24—H24A	121.1
C1—C10—H10A	119.8	C25—C24—H24A	121.1
C9—C10—H10A	119.8	C24—C25—C20	119.57 (16)
O1—C11—N1	121.73 (17)	C24—C25—N4	129.14 (16)
O1—C11—C1	123.84 (17)	C20—C25—N4	111.30 (15)
N1—C11—C1	114.43 (15)	N4—C26—N3	113.31 (15)
C13—C12—C17	122.72 (17)	N4—C26—C6	127.72 (15)
C13—C12—N1	132.31 (17)	N3—C26—C6	118.96 (15)
C10—C1—C2—C7	0.3 (2)	N1—C12—C17—C16	179.41 (16)
C11—C1—C2—C7	178.79 (14)	C13—C12—C17—N2	179.05 (15)
C10—C1—C2—C3	−178.41 (16)	N1—C12—C17—N2	−0.76 (19)
C11—C1—C2—C3	0.1 (2)	C18—N2—C17—C16	−179.52 (18)
C7—C2—C3—C4	−1.9 (2)	C18—N2—C17—C12	0.67 (19)
C1—C2—C3—C4	176.75 (15)	C17—N2—C18—N1	−0.31 (19)
C7—C2—C3—C18	178.01 (14)	C17—N2—C18—C3	179.41 (16)
C1—C2—C3—C18	−3.3 (2)	C11—N1—C18—N2	177.90 (16)
C2—C3—C4—C5	2.5 (3)	C12—N1—C18—N2	−0.14 (19)
C18—C3—C4—C5	−177.47 (15)	C11—N1—C18—C3	−1.9 (2)
C3—C4—C5—C6	−1.1 (3)	C12—N1—C18—C3	−179.89 (14)
C4—C5—C6—C7	−0.8 (2)	C4—C3—C18—N2	4.4 (3)
C4—C5—C6—C26	−179.71 (15)	C2—C3—C18—N2	−175.56 (16)
C1—C2—C7—C6	−178.63 (14)	C4—C3—C18—N1	−175.92 (15)
C3—C2—C7—C6	0.1 (2)	C2—C3—C18—N1	4.1 (2)
C1—C2—C7—C8	0.8 (2)	C26—N3—C19—O2	−179.87 (16)
C3—C2—C7—C8	179.53 (14)	C20—N3—C19—O2	−2.1 (3)
C5—C6—C7—C2	1.3 (2)	C26—N3—C19—C8	0.9 (2)
C26—C6—C7—C2	−179.75 (14)	C20—N3—C19—C8	178.74 (15)
C5—C6—C7—C8	−178.17 (15)	C9—C8—C19—O2	2.0 (3)
C26—C6—C7—C8	0.8 (2)	C7—C8—C19—O2	−178.00 (16)
C2—C7—C8—C9	−1.5 (2)	C9—C8—C19—N3	−178.80 (15)
C6—C7—C8—C9	177.92 (15)	C7—C8—C19—N3	1.2 (2)
C2—C7—C8—C19	178.52 (14)	C19—N3—C20—C21	4.0 (3)
C6—C7—C8—C19	−2.0 (2)	C26—N3—C20—C21	−177.86 (17)
C7—C8—C9—C10	1.1 (3)	C19—N3—C20—C25	−177.90 (15)
C19—C8—C9—C10	−178.94 (16)	C26—N3—C20—C25	0.25 (17)
C2—C1—C10—C9	−0.7 (3)	C25—C20—C21—C22	2.1 (3)
C11—C1—C10—C9	−179.27 (15)	N3—C20—C21—C22	179.92 (16)
C8—C9—C10—C1	0.0 (3)	C20—C21—C22—C23	−0.8 (3)
C18—N1—C11—O1	178.06 (16)	C21—C22—C23—C24	−1.0 (3)
C12—N1—C11—O1	−4.3 (3)	C22—C23—C24—C25	1.4 (3)
C18—N1—C11—C1	−1.3 (2)	C23—C24—C25—C20	−0.2 (3)
C12—N1—C11—C1	176.29 (15)	C23—C24—C25—N4	−179.75 (17)
C10—C1—C11—O1	1.4 (3)	C21—C20—C25—C24	−1.7 (3)
C2—C1—C11—O1	−177.17 (16)	N3—C20—C25—C24	−179.97 (15)
C10—C1—C11—N1	−179.26 (15)	C21—C20—C25—N4	177.99 (15)
C2—C1—C11—N1	2.2 (2)	N3—C20—C25—N4	−0.34 (18)
C11—N1—C12—C13	2.8 (3)	C26—N4—C25—C24	179.87 (17)
C18—N1—C12—C13	−179.25 (18)	C26—N4—C25—C20	0.28 (18)
C11—N1—C12—C17	−177.46 (16)	C25—N4—C26—N3	−0.11 (18)
C18—N1—C12—C17	0.53 (17)	C25—N4—C26—C6	−179.84 (16)
C17—C12—C13—C14	0.0 (3)	C19—N3—C26—N4	178.09 (15)
N1—C12—C13—C14	179.79 (17)	C20—N3—C26—N4	−0.10 (19)
C12—C13—C14—C15	0.6 (3)	C19—N3—C26—C6	−2.1 (2)
C13—C14—C15—C16	−0.6 (3)	C20—N3—C26—C6	179.66 (14)
C14—C15—C16—C17	−0.2 (3)	C5—C6—C26—N4	−0.1 (3)
C15—C16—C17—C12	0.8 (3)	C7—C6—C26—N4	−179.10 (16)
C15—C16—C17—N2	−178.99 (17)	C5—C6—C26—N3	−179.86 (15)
C13—C12—C17—C16	−0.8 (3)	C7—C6—C26—N3	1.2 (2)

(polymorph2)

Crystal data

C26H12N4O2	Dx = 1.559 Mg m^−3
Mr = 412.40	Melting point: 741 K
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 16.971 (2) Å	Cell parameters from 1796 reflections
b = 7.3707 (9) Å	θ = 2.6–72.3°
c = 14.0809 (17) Å	µ = 0.83 mm^−1
β = 94.09 (1)°	T = 130 K
V = 1756.8 (4) Å^3	Plate, dark red
Z = 4	0.14 × 0.08 × 0.01 mm
F(000) = 848

Data collection

BRUKER AXS (Kappa APEX II Duo) diffractometer	1498 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
Graphite monochromator	θmax = 50.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements) R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38	h = −16→16
Tmin = 0.890, Tmax = 0.989	k = −7→7
1794 measured reflections	l = −13→13
1794 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.110	H-atom parameters constrained
wR(F^2) = 0.321	w = 1/[σ^2(Fo^2) + (0.1921P)^2 + 7.3569P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.055
1794 reflections	Δρmax = 0.74 e Å^−3
290 parameters	Δρmin = −0.53 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (12)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.9318 (4)	0.1829 (9)	0.9837 (6)	0.025 (2)
N3	0.5571 (4)	−0.1941 (10)	0.9621 (6)	0.030 (2)
C2	0.7827 (5)	0.0397 (11)	0.9767 (8)	0.027 (2)
C1	0.8203 (5)	0.0628 (12)	0.8906 (7)	0.027 (2)
C7	0.7053 (5)	−0.0487 (12)	0.9727 (7)	0.026 (2)
C3	0.8185 (5)	0.0904 (12)	1.0668 (7)	0.029 (3)
O1	0.9374 (4)	0.1650 (9)	0.8231 (6)	0.043 (2)
C6	0.6687 (5)	−0.0713 (11)	1.0593 (6)	0.023 (2)
N4	0.5446 (4)	−0.1890 (10)	1.1219 (7)	0.030 (2)
O2	0.5527 (4)	−0.2316 (10)	0.8032 (6)	0.044 (2)
C19	0.5917 (6)	−0.1767 (12)	0.8761 (8)	0.029 (3)
C26	0.5925 (5)	−0.1514 (12)	1.0495 (8)	0.025 (2)
C8	0.6699 (5)	−0.0953 (11)	0.8841 (7)	0.026 (2)
N2	0.9422 (4)	0.2268 (10)	1.1407 (5)	0.025 (2)
C5	0.7076 (5)	−0.0181 (12)	1.1476 (7)	0.031 (3)
H5	0.6828	−0.0405	1.2048	0.037*
C11	0.8975 (6)	0.1380 (12)	0.8933 (9)	0.035 (3)
C18	0.8944 (5)	0.1663 (11)	1.0670 (7)	0.027 (3)
C9	0.7082 (6)	−0.0681 (14)	0.8010 (7)	0.035 (3)
H9	0.6826	−0.1026	0.7415	0.043*
C10	0.7810 (6)	0.0066 (13)	0.8035 (8)	0.038 (3)
H10	0.8062	0.0217	0.7459	0.046*
C4	0.7793 (5)	0.0640 (12)	1.1520 (7)	0.029 (3)
H4	0.8033	0.1037	1.2115	0.034*
C20	0.4830 (5)	−0.2732 (12)	0.9790 (8)	0.027 (3)
C22	0.3572 (6)	−0.4096 (12)	0.9563 (9)	0.036 (3)
H22	0.3151	−0.4580	0.9159	0.044*
C14	1.1353 (5)	0.3798 (13)	0.9991 (8)	0.033 (3)
H14	1.1798	0.4100	0.9649	0.040*
C15	1.1406 (6)	0.4083 (13)	1.0947 (8)	0.036 (3)
H15	1.1878	0.4583	1.1241	0.043*
C21	0.4237 (6)	−0.3440 (12)	0.9149 (8)	0.034 (3)
H21	0.4286	−0.3470	0.8481	0.041*
C23	0.3498 (6)	−0.4076 (13)	1.0502 (8)	0.034 (3)
H23	0.3032	−0.4555	1.0741	0.041*
C17	1.0135 (6)	0.2878 (12)	1.1027 (8)	0.036 (3)
C12	1.0069 (5)	0.2655 (11)	1.0051 (7)	0.018 (2)
C25	0.4751 (6)	−0.2689 (13)	1.0758 (7)	0.028 (3)
C13	1.0685 (6)	0.3088 (13)	0.9477 (8)	0.038 (3)
H13	1.0652	0.2917	0.8807	0.045*
C16	1.0794 (6)	0.3666 (13)	1.1503 (8)	0.039 (3)
H16	1.0821	0.3901	1.2167	0.047*
C24	0.4092 (5)	−0.3364 (12)	1.1147 (8)	0.034 (3)
H24	0.4040	−0.3351	1.1814	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.022 (4)	0.014 (4)	0.041 (6)	0.003 (3)	0.006 (4)	0.002 (4)
N3	0.027 (5)	0.033 (5)	0.029 (6)	−0.005 (4)	−0.011 (5)	−0.006 (4)
C2	0.023 (5)	0.018 (5)	0.041 (7)	−0.006 (4)	0.005 (5)	−0.001 (5)
C1	0.019 (5)	0.023 (5)	0.038 (7)	0.003 (4)	0.002 (5)	0.015 (5)
C7	0.024 (5)	0.022 (5)	0.034 (7)	0.003 (4)	0.000 (5)	−0.010 (5)
C3	0.016 (5)	0.032 (6)	0.039 (7)	0.009 (4)	0.012 (5)	0.005 (5)
O1	0.029 (4)	0.052 (5)	0.048 (5)	−0.003 (3)	0.012 (4)	0.009 (4)
C6	0.027 (6)	0.020 (5)	0.021 (6)	0.004 (4)	0.004 (5)	−0.004 (5)
N4	0.017 (4)	0.026 (5)	0.048 (6)	0.001 (3)	0.012 (4)	−0.002 (4)
O2	0.040 (4)	0.049 (5)	0.042 (5)	−0.013 (4)	−0.006 (4)	−0.015 (4)
C19	0.040 (6)	0.017 (5)	0.030 (7)	0.006 (4)	0.012 (6)	0.010 (5)
C26	0.011 (5)	0.021 (5)	0.046 (7)	0.008 (4)	0.011 (5)	0.010 (5)
C8	0.021 (5)	0.021 (5)	0.036 (7)	−0.009 (4)	0.002 (5)	−0.001 (5)
N2	0.024 (4)	0.024 (4)	0.025 (5)	0.001 (4)	−0.005 (4)	−0.004 (4)
C5	0.031 (6)	0.028 (6)	0.034 (7)	0.005 (5)	0.007 (5)	0.010 (5)
C11	0.025 (6)	0.028 (6)	0.051 (8)	−0.002 (5)	0.010 (6)	0.002 (5)
C18	0.030 (6)	0.018 (5)	0.031 (7)	0.006 (4)	0.002 (6)	0.002 (5)
C9	0.034 (6)	0.047 (7)	0.025 (7)	−0.001 (5)	−0.003 (5)	−0.004 (5)
C10	0.039 (7)	0.043 (7)	0.035 (7)	0.000 (5)	0.011 (5)	−0.003 (6)
C4	0.016 (5)	0.034 (6)	0.036 (7)	−0.003 (4)	0.001 (5)	−0.011 (5)
C20	0.011 (5)	0.020 (5)	0.051 (9)	−0.013 (4)	0.001 (5)	0.001 (5)
C22	0.026 (6)	0.018 (5)	0.067 (9)	0.000 (4)	0.016 (6)	0.007 (6)
C14	0.014 (5)	0.031 (6)	0.054 (8)	−0.001 (4)	0.008 (5)	−0.002 (5)
C15	0.025 (6)	0.041 (6)	0.041 (8)	0.000 (5)	−0.007 (5)	−0.006 (6)
C21	0.034 (6)	0.027 (6)	0.043 (7)	0.010 (5)	0.005 (5)	0.008 (5)
C23	0.018 (5)	0.033 (6)	0.052 (8)	0.003 (5)	0.013 (5)	0.008 (5)
C17	0.031 (6)	0.025 (6)	0.051 (9)	0.000 (5)	0.000 (6)	0.014 (5)
C12	0.017 (5)	0.021 (5)	0.017 (6)	−0.015 (4)	0.004 (4)	−0.002 (4)
C25	0.033 (7)	0.029 (6)	0.021 (7)	0.016 (5)	0.007 (5)	0.001 (5)
C13	0.043 (7)	0.027 (6)	0.044 (7)	0.006 (5)	0.005 (6)	−0.001 (5)
C16	0.031 (6)	0.039 (6)	0.048 (7)	−0.003 (5)	0.010 (6)	−0.008 (5)
C24	0.021 (6)	0.035 (6)	0.044 (7)	0.000 (4)	0.002 (6)	−0.002 (5)

Geometric parameters (Å, º)

N1—C18	1.378 (13)	C5—H5	0.9500
N1—C11	1.401 (13)	C9—C10	1.351 (14)
N1—C12	1.425 (11)	C9—H9	0.9500
N3—C26	1.368 (13)	C10—H10	0.9500
N3—C19	1.389 (14)	C4—H4	0.9500
N3—C20	1.421 (12)	C20—C25	1.379 (14)
C2—C1	1.419 (14)	C20—C21	1.405 (14)
C2—C3	1.417 (15)	C22—C23	1.336 (16)
C2—C7	1.464 (13)	C22—C21	1.394 (14)
C1—C10	1.417 (15)	C22—H22	0.9500
C1—C11	1.420 (13)	C14—C15	1.359 (15)
C7—C8	1.389 (14)	C14—C13	1.403 (14)
C7—C6	1.417 (14)	C14—H14	0.9500
C3—C18	1.405 (13)	C15—C16	1.379 (14)
C3—C4	1.426 (14)	C15—H15	0.9500
O1—C11	1.254 (13)	C21—H21	0.9500
C6—C26	1.420 (13)	C23—C24	1.410 (15)
C6—C5	1.420 (14)	C23—H23	0.9500
N4—C26	1.376 (13)	C17—C12	1.380 (15)
N4—C25	1.432 (12)	C17—C16	1.389 (14)
O2—C19	1.249 (13)	C12—C13	1.403 (13)
C19—C8	1.453 (14)	C25—C24	1.372 (14)
C8—C9	1.393 (15)	C13—H13	0.9500
N2—C18	1.347 (12)	C16—H16	0.9500
N2—C17	1.430 (13)	C24—H24	0.9500
C5—C4	1.357 (13)
C18—N1—C11	124.4 (8)	C8—C9—H9	119.4
C18—N1—C12	108.5 (8)	C9—C10—C1	121.0 (10)
C11—N1—C12	126.9 (8)	C9—C10—H10	119.5
C26—N3—C19	125.3 (8)	C1—C10—H10	119.5
C26—N3—C20	106.3 (8)	C5—C4—C3	119.5 (9)
C19—N3—C20	128.2 (8)	C5—C4—H4	120.3
C1—C2—C3	122.9 (8)	C3—C4—H4	120.3
C1—C2—C7	118.6 (9)	C25—C20—C21	121.8 (9)
C3—C2—C7	118.5 (9)	C25—C20—N3	107.9 (8)
C2—C1—C10	119.4 (8)	C21—C20—N3	130.3 (10)
C2—C1—C11	119.6 (10)	C23—C22—C21	123.1 (11)
C10—C1—C11	120.9 (10)	C23—C22—H22	118.5
C8—C7—C6	123.7 (8)	C21—C22—H22	118.5
C8—C7—C2	118.3 (9)	C15—C14—C13	124.2 (10)
C6—C7—C2	117.8 (9)	C15—C14—H14	117.9
C18—C3—C2	116.2 (9)	C13—C14—H14	117.9
C18—C3—C4	122.3 (9)	C14—C15—C16	121.9 (9)
C2—C3—C4	121.5 (8)	C14—C15—H15	119.1
C7—C6—C26	114.7 (9)	C16—C15—H15	119.0
C7—C6—C5	121.1 (8)	C22—C21—C20	115.1 (10)
C26—C6—C5	124.2 (9)	C22—C21—H21	122.4
C26—N4—C25	105.0 (8)	C20—C21—H21	122.4
O2—C19—N3	117.0 (8)	C22—C23—C24	121.9 (10)
O2—C19—C8	128.7 (9)	C22—C23—H23	119.0
N3—C19—C8	114.3 (9)	C24—C23—H23	119.1
N3—C26—N4	112.0 (8)	C12—C17—C16	122.4 (9)
N3—C26—C6	121.4 (9)	C12—C17—N2	108.9 (8)
N4—C26—C6	126.5 (10)	C16—C17—N2	128.6 (10)
C7—C8—C9	121.4 (8)	C17—C12—C13	122.4 (9)
C7—C8—C19	120.5 (9)	C17—C12—N1	105.6 (8)
C9—C8—C19	118.2 (9)	C13—C12—N1	131.8 (9)
C18—N2—C17	107.1 (8)	C24—C25—C20	121.8 (10)
C4—C5—C6	121.5 (9)	C24—C25—N4	129.4 (9)
C4—C5—H5	119.2	C20—C25—N4	108.8 (8)
C6—C5—H5	119.3	C14—C13—C12	113.3 (10)
O1—C11—N1	117.8 (8)	C14—C13—H13	123.3
O1—C11—C1	126.2 (11)	C12—C13—H13	123.3
N1—C11—C1	116.0 (10)	C15—C16—C17	115.6 (10)
N2—C18—N1	109.7 (8)	C15—C16—H16	122.2
N2—C18—C3	129.4 (9)	C17—C16—H16	122.2
N1—C18—C3	120.8 (9)	C25—C24—C23	116.3 (10)
C10—C9—C8	121.2 (10)	C25—C24—H24	121.9
C10—C9—H9	119.4	C23—C24—H24	121.8