Local structure in the disordered solid solution of cis- and trans-perinones

The cis- and trans-isomers of the polycyclic aromatic compound perinone, C₂₆H₁₂N₄O₂, form a solid solution (Vat Red 14). This solid solution is isotypic to the crystal structures of cis-perinone (Pigment Red 194) and trans-perinone (Pigment Orange 34) and exhibits a combined positional and orientational disorder: In the crystal, each molecular position is occupied by either a cis- or trans-perinone molecule, both of which have two possible molecular orientations. The structure of cis-perinone exhibits a twofold orientational disorder, whereas the structure of trans-perinone is ordered. The crystal structure of the solid solution was determined by single-crystal X-ray analysis. Extensive lattice-energy minimizations with force-field and DFT-D methods were carried out on combinatorially complete sets of ordered models. For the disordered systems, local structures were calculated, including preferred local arrangements, ordering lengths, and probabilities for the arrangement of neighbouring molecules. The superposition of the atomic positions of all energetically favourable calculated models corresponds well with the experimentally determined crystal structures, explaining not only the atomic positions, but also the site occupancies and anisotropic displacement parameters.

Computing details

Data collection: SMART V5.628 (BRUKER AXS, 2001) for solid_solution_293K_Cu. Cell refinement: SAINT V6.45 (BRUKER AXS, 2003) for solid_solution_293K_Cu. Data reduction: SAINT V6.45 (BRUKER AXS, 2003) for solid_solution_293K_Cu. Program(s) used to solve structure: L.J. Bourhis et al., in preparation (2013) for solid_solution_100K_Cu; SHELXS97 (Sheldrick, 1990) for solid_solution_293K_Cu, solid_solution_293K_Mo. Program(s) used to refine structure: SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for solid_solution_100K_Cu; SHELXL2013 (Sheldrick, 2013) for solid_solution_293K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Mo. Molecular graphics: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for solid_solution_100K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Cu. Software used to prepare material for publication: O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for solid_solution_100K_Cu; SHELXL97 (Sheldrick, 1997) for solid_solution_293K_Cu.

(solid_solution_100K_Cu)

Crystal data

C26H12N4O2	Z = 2
Mr = 412.40	F(000) = 424
Monoclinic, P21/c	Dx = 1.530 Mg m^−3
a = 11.7955 (11) Å	Cu Kα radiation, λ = 1.54186 Å
b = 4.7680 (4) Å	µ = 0.82 mm^−1
c = 16.1261 (14) Å	T = 100 K
β = 99.354 (7)°	0.3 × 0.06 × 0.02 mm
V = 894.89 (14) Å^3

Data collection

8541 measured reflections	θmax = 68.0°, θmin = 3.8°
1562 independent reflections	h = −13→14
953 reflections with I > 2σ(I)	k = −5→5
Rint = 0.042	l = −18→17

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.084	w = 1/[σ^2(Fo^2) + (0.1665P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.246	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.52 e Å^−3
1562 reflections	Δρmin = −0.42 e Å^−3
205 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
19 restraints	Extinction coefficient: 0.038 (8)
Primary atom site location: iterative

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	Occ. (<1)
N001	0.7858 (3)	0.4996 (5)	0.4361 (2)	0.0776 (11)
C007	0.8723 (3)	0.9877 (6)	0.6120 (2)	0.0702 (11)
H007	0.8149	0.9510	0.6457	0.084*
C008	0.8673 (4)	0.5474 (6)	0.3849 (3)	0.0763 (12)
C009	1.0418 (3)	0.8128 (6)	0.3617 (2)	0.0718 (11)
H009	1.0412	0.7161	0.3102	0.086*
C010	0.7801 (4)	0.6364 (7)	0.5116 (3)	0.0779 (13)
C011	0.8712 (3)	0.8442 (6)	0.5371 (2)	0.0658 (10)
C012	0.9566 (3)	0.8986 (5)	0.4865 (2)	0.0619 (10)
C013	0.9581 (3)	0.7556 (6)	0.4100 (2)	0.0651 (10)
C101	0.7097 (3)	0.2961 (6)	0.3989 (2)	0.0655 (10)
O101	0.6997 (4)	0.5808 (9)	0.5572 (3)	0.0693 (13)	0.789 (7)
N101	0.8509 (5)	0.3957 (12)	0.3204 (4)	0.0638 (15)	0.789 (7)
C100	0.7515 (4)	0.2321 (8)	0.3267 (3)	0.0669 (14)	0.789 (7)
C102	0.6104 (5)	0.1657 (9)	0.4208 (4)	0.0755 (15)	0.789 (7)
H102	0.5792	0.2141	0.4696	0.091*	0.789 (7)
C103	0.5628 (7)	−0.0412 (13)	0.3637 (5)	0.077 (2)	0.789 (7)
H103	0.4978	−0.1417	0.3757	0.093*	0.789 (7)
C104	0.6058 (6)	−0.1079 (11)	0.2900 (5)	0.091 (2)	0.789 (7)
H104	0.5694	−0.2482	0.2532	0.109*	0.789 (7)
C105	0.7003 (5)	0.0297 (9)	0.2714 (4)	0.0788 (16)	0.789 (7)
H105	0.7302	−0.0128	0.2216	0.095*	0.789 (7)
N201	0.7140 (19)	0.541 (4)	0.5208 (12)	0.053 (5)	0.211 (7)
O201	0.894 (2)	0.399 (5)	0.2969 (14)	0.079 (6)	0.211 (7)
C202	0.6844 (17)	0.087 (3)	0.3328 (16)	0.079 (5)	0.211 (7)
H202	0.7357	0.0633	0.2937	0.094*	0.211 (7)
C203	0.593 (2)	−0.066 (5)	0.3264 (17)	0.050 (5)*	0.211 (7)
H203	0.5716	−0.1961	0.2821	0.059*	0.211 (7)
C204	0.522 (2)	−0.015 (5)	0.399 (2)	0.080 (7)	0.211 (7)
H204	0.4529	−0.1202	0.3977	0.096*	0.211 (7)
C205	0.5528 (16)	0.181 (4)	0.4678 (16)	0.081 (5)	0.211 (7)
H205	0.5088	0.2042	0.5116	0.097*	0.211 (7)
C200	0.6530 (13)	0.331 (3)	0.4639 (12)	0.067 (4)	0.211 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N001	0.089 (2)	0.0434 (14)	0.086 (2)	−0.0123 (14)	−0.0300 (18)	0.0132 (14)
C007	0.085 (2)	0.0453 (16)	0.072 (2)	0.0003 (15)	−0.0111 (18)	0.0071 (15)
C008	0.101 (3)	0.0365 (15)	0.075 (3)	0.0001 (15)	−0.034 (2)	0.0023 (15)
C009	0.095 (2)	0.0429 (16)	0.068 (2)	0.0023 (15)	−0.0178 (19)	−0.0022 (15)
C010	0.083 (3)	0.0435 (18)	0.093 (3)	−0.0037 (17)	−0.029 (2)	0.0083 (18)
C011	0.078 (2)	0.0378 (15)	0.071 (2)	−0.0019 (13)	−0.0191 (18)	0.0082 (13)
C012	0.076 (2)	0.0349 (13)	0.064 (2)	−0.0043 (13)	−0.0207 (17)	0.0032 (13)
C013	0.083 (2)	0.0393 (15)	0.063 (2)	−0.0028 (14)	−0.0189 (17)	0.0016 (13)
C101	0.074 (2)	0.0369 (14)	0.074 (2)	−0.0040 (13)	−0.0216 (17)	0.0015 (14)
O101	0.075 (3)	0.059 (2)	0.072 (3)	−0.0068 (17)	0.007 (2)	0.007 (2)
N101	0.083 (4)	0.0404 (18)	0.058 (4)	0.003 (2)	−0.017 (2)	−0.007 (2)
C100	0.083 (3)	0.036 (2)	0.068 (3)	0.005 (2)	−0.028 (2)	−0.0031 (17)
C102	0.080 (3)	0.048 (2)	0.087 (4)	−0.008 (2)	−0.024 (3)	0.003 (2)
C103	0.068 (5)	0.049 (3)	0.102 (7)	−0.008 (3)	−0.025 (4)	−0.001 (4)
C104	0.106 (4)	0.051 (2)	0.097 (5)	0.000 (3)	−0.037 (4)	−0.015 (3)
C105	0.089 (3)	0.046 (2)	0.085 (4)	0.008 (2)	−0.036 (3)	−0.009 (2)
N201	0.057 (9)	0.055 (9)	0.053 (12)	0.020 (7)	0.030 (10)	0.014 (8)
O201	0.097 (15)	0.067 (8)	0.071 (12)	−0.001 (9)	0.009 (9)	−0.021 (7)
C202	0.080 (11)	0.036 (7)	0.107 (14)	−0.018 (8)	−0.024 (10)	−0.016 (8)
C204	0.073 (16)	0.036 (9)	0.11 (2)	−0.013 (10)	−0.033 (12)	0.027 (9)
C205	0.058 (9)	0.073 (11)	0.100 (15)	−0.007 (8)	−0.019 (8)	0.018 (9)
C200	0.058 (8)	0.048 (8)	0.087 (10)	−0.003 (6)	−0.017 (7)	0.001 (7)

Geometric parameters (Å, º)

N001—C008	1.383 (5)	C101—C202	1.45 (2)
N001—C010	1.392 (6)	C101—C200	1.34 (2)
N001—C101	1.390 (4)	N101—C100	1.425 (8)
N001—C200	1.879 (17)	C100—C105	1.384 (6)
C007—H007	0.9500	C102—H102	0.9500
C007—C009^i	1.404 (5)	C102—C103	1.402 (7)
C007—C011	1.388 (5)	C103—H103	0.9500
C008—C013	1.468 (5)	C103—C104	1.402 (10)
C008—N101	1.256 (7)	C104—H104	0.9500
C008—O201	1.66 (2)	C104—C105	1.369 (9)
C009—C007^i	1.404 (5)	C105—H105	0.9500
C009—H009	0.9500	N201—C200	1.47 (3)
C009—C013	1.380 (5)	C202—H202	0.9500
C010—C011	1.471 (5)	C202—C203	1.29 (3)
C010—O101	1.318 (7)	C203—H203	0.9500
C010—N201	0.93 (2)	C203—C204	1.57 (3)
C011—C012	1.419 (5)	C204—H204	0.9500
C012—C012^i	1.424 (6)	C204—C205	1.45 (3)
C012—C013	1.412 (5)	C205—H205	0.9500
C101—C100	1.370 (6)	C205—C200	1.39 (2)
C101—C102	1.421 (7)
C008—N001—C010	125.6 (3)	C200—C101—C202	126.0 (12)
C008—N001—C101	108.6 (3)	C008—N101—C100	105.9 (5)
C008—N001—C200	154.1 (6)	C101—C100—N101	110.6 (4)
C010—N001—C200	80.2 (6)	C101—C100—C105	121.5 (5)
C101—N001—C010	125.8 (4)	C105—C100—N101	127.9 (5)
C101—N001—C200	45.5 (6)	C101—C102—H102	123.1
C009^i—C007—H007	120.0	C103—C102—C101	113.8 (6)
C011—C007—H007	120.0	C103—C102—H102	123.1
C011—C007—C009^i	120.0 (4)	C102—C103—H103	118.2
N001—C008—C013	119.5 (3)	C104—C103—C102	123.6 (7)
N001—C008—O201	133.5 (9)	C104—C103—H103	118.2
C013—C008—O201	106.8 (9)	C103—C104—H104	120.1
N101—C008—N001	111.8 (4)	C105—C104—C103	119.8 (6)
N101—C008—C013	128.6 (5)	C105—C104—H104	120.1
C007^i—C009—H009	119.6	C100—C105—H105	120.7
C013—C009—C007^i	120.8 (3)	C104—C105—C100	118.6 (6)
C013—C009—H009	119.6	C104—C105—H105	120.7
N001—C010—C011	115.0 (4)	C010—N201—C200	124.7 (17)
O101—C010—N001	122.4 (4)	C101—C202—H202	119.5
O101—C010—C011	122.6 (4)	C203—C202—C101	121 (2)
N201—C010—N001	94.1 (13)	C203—C202—H202	119.5
N201—C010—C011	150.9 (14)	C202—C203—H203	123.3
C007—C011—C010	118.6 (4)	C202—C203—C204	113 (2)
C007—C011—C012	120.2 (3)	C204—C203—H203	123.3
C012—C011—C010	121.2 (4)	C203—C204—H204	117.7
C011—C012—C012^i	119.4 (4)	C205—C204—C203	125 (2)
C013—C012—C011	121.6 (3)	C205—C204—H204	117.7
C013—C012—C012^i	119.0 (4)	C204—C205—H205	122.9
C009—C013—C008	122.3 (3)	C200—C205—C204	114 (2)
C009—C013—C012	120.6 (3)	C200—C205—H205	122.9
C012—C013—C008	117.1 (4)	C101—C200—N001	47.6 (6)
N001—C101—C102	134.3 (4)	C101—C200—N201	108.5 (13)
N001—C101—C202	146.8 (10)	C101—C200—C205	120.4 (17)
C100—C101—N001	103.1 (4)	N201—C200—N001	60.9 (9)
C100—C101—C102	122.6 (4)	C205—C200—N001	167.9 (18)
C200—C101—N001	86.8 (7)	C205—C200—N201	131 (2)
N001—C008—C013—C009	180.0 (3)	C101—N001—C010—O101	1.0 (6)
N001—C008—C013—C012	−0.2 (4)	C101—N001—C010—N201	−0.1 (12)
N001—C008—N101—C100	0.2 (5)	C101—N001—C200—N201	178.8 (12)
N001—C010—C011—C007	−179.3 (3)	C101—N001—C200—C205	−7 (6)
N001—C010—C011—C012	0.7 (4)	C101—C100—C105—C104	0.0 (6)
N001—C010—N201—C200	−0.9 (19)	C101—C102—C103—C104	−2.3 (9)
N001—C101—C100—N101	−0.3 (4)	C101—C202—C203—C204	−4 (4)
N001—C101—C100—C105	178.7 (3)	O101—C010—C011—C007	−0.2 (5)
N001—C101—C102—C103	−177.7 (4)	O101—C010—C011—C012	179.9 (3)
N001—C101—C202—C203	178.3 (16)	O101—C010—N201—C200	−179 (4)
N001—C101—C200—N201	−1.1 (11)	N101—C008—C013—C009	0.2 (6)
N001—C101—C200—C205	178.3 (14)	N101—C008—C013—C012	−180.0 (4)
C007^i—C009—C013—C008	−179.6 (3)	N101—C100—C105—C104	178.8 (5)
C007^i—C009—C013—C012	0.5 (5)	C100—C101—C102—C103	2.5 (6)
C007—C011—C012—C012^i	0.1 (5)	C100—C101—C202—C203	−168 (3)
C007—C011—C012—C013	179.8 (3)	C100—C101—C200—N001	−171 (4)
C008—N001—C010—C011	−1.0 (5)	C100—C101—C200—N201	−172 (3)
C008—N001—C010—O101	179.8 (4)	C100—C101—C200—C205	7 (5)
C008—N001—C010—N201	178.7 (12)	C102—C101—C100—N101	179.5 (4)
C008—N001—C101—C100	0.5 (3)	C102—C101—C100—C105	−1.5 (5)
C008—N001—C101—C102	−179.3 (4)	C102—C101—C202—C203	5 (2)
C008—N001—C101—C202	10.1 (14)	C102—C101—C200—N001	178.7 (7)
C008—N001—C101—C200	−178.0 (7)	C102—C101—C200—N201	177.6 (16)
C008—N001—C200—C101	4.3 (14)	C102—C101—C200—C205	−3.0 (10)
C008—N001—C200—N201	−176.9 (11)	C102—C103—C104—C105	1.0 (10)
C008—N001—C200—C205	−3 (7)	C103—C104—C105—C100	0.3 (8)
C008—N101—C100—C101	0.1 (5)	N201—C010—C011—C007	1 (3)
C008—N101—C100—C105	−178.8 (4)	N201—C010—C011—C012	−179 (2)
C009^i—C007—C011—C010	179.9 (3)	O201—C008—C013—C009	3.7 (9)
C009^i—C007—C011—C012	−0.1 (5)	O201—C008—C013—C012	−176.5 (9)
C010—N001—C008—C013	0.8 (5)	O201—C008—N101—C100	171 (3)
C010—N001—C008—N101	−179.4 (4)	C202—C101—C100—N101	−172.8 (11)
C010—N001—C008—O201	175.9 (12)	C202—C101—C100—C105	6.2 (11)
C010—N001—C101—C100	179.4 (3)	C202—C101—C102—C103	−3.0 (9)
C010—N001—C101—C102	−0.4 (6)	C202—C101—C200—N001	174.5 (10)
C010—N001—C101—C202	−171.0 (14)	C202—C101—C200—N201	173.4 (12)
C010—N001—C101—C200	0.9 (7)	C202—C101—C200—C205	−7.2 (19)
C010—N001—C200—C101	−179.2 (6)	C202—C203—C204—C205	−1 (4)
C010—N001—C200—N201	−0.4 (9)	C203—C204—C205—C200	2 (4)
C010—N001—C200—C205	174 (6)	C204—C205—C200—N001	8 (7)
C010—C011—C012—C012^i	−180.0 (3)	C204—C205—C200—C101	2 (2)
C010—C011—C012—C013	−0.2 (4)	C204—C205—C200—N201	−178.6 (19)
C010—N201—C200—N001	0.8 (16)	C200—N001—C008—C013	176.5 (11)
C010—N201—C200—C101	2 (2)	C200—N001—C008—N101	−3.7 (12)
C010—N201—C200—C205	−177.5 (18)	C200—N001—C008—O201	−8.4 (17)
C011—C010—N201—C200	178.6 (9)	C200—N001—C010—C011	−179.1 (5)
C011—C012—C013—C008	−0.1 (4)	C200—N001—C010—O101	1.7 (6)
C011—C012—C013—C009	179.8 (3)	C200—N001—C010—N201	0.6 (13)
C012^i—C012—C013—C008	179.7 (3)	C200—N001—C101—C100	178.5 (7)
C012^i—C012—C013—C009	−0.5 (5)	C200—N001—C101—C102	−1.3 (7)
C013—C008—N101—C100	180.0 (3)	C200—N001—C101—C202	−171.9 (16)
C101—N001—C008—C013	179.7 (3)	C200—C101—C100—N101	171 (4)
C101—N001—C008—N101	−0.4 (5)	C200—C101—C100—C105	−10 (4)
C101—N001—C008—O201	−5.2 (12)	C200—C101—C102—C103	−179.5 (10)
C101—N001—C010—C011	−179.8 (3)	C200—C101—C202—C203	8 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

(solid_solution_293K_Cu)

Crystal data

C26H12N4O2	F(000) = 424
Mr = 412.40	Dx = 1.505 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 11.808 (3) Å	Cell parameters from 3946 reflections
b = 4.8032 (10) Å	θ = 5.5–49.5°
c = 16.246 (4) Å	µ = 0.80 mm^−1
β = 99.002 (9)°	T = 293 K
V = 910.1 (4) Å^3	Plate, brown
Z = 2	0.30 × 0.13 × 0.02 mm

Data collection

Bruker AXS three circle goniometer diffractometer	1677 independent reflections
Radiation source: Incoatec IµS microfocus X-ray source, micro focus source	1225 reflections with I > 2σ(I)
Incoatec Quazar Multilayer Mirror monochromator	Rint = 0.037
Detector resolution: 8.33 pixels mm^-1	θmax = 69.6°, θmin = 3.8°
ω scan	h = −14→13
Absorption correction: empirical (using intensity measurements) (G. M. Sheldrick. SADABS), 2008.)	k = −5→5
Tmin = 0.614, Tmax = 0.753	l = −19→19
9979 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 0.4338P] where P = (Fo^2 + 2Fc^2)/3
1677 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.16 e Å^−3
24 restraints	Δρmin = −0.11 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	Occ. (<1)
N001	0.71361 (19)	0.5051 (4)	0.06401 (14)	0.0801 (7)
C001	0.6262 (2)	0.9812 (5)	−0.11143 (15)	0.0766 (7)
H001	0.6822	0.9438	−0.1442	0.092*
C002	0.4591 (2)	0.8221 (5)	0.13789 (15)	0.0776 (7)
H002	0.4600	0.7314	0.1886	0.093*
C003	0.5420 (2)	0.7614 (4)	0.08927 (14)	0.0659 (6)
C004	0.54320 (19)	0.8999 (4)	0.01330 (13)	0.0619 (6)
C005	0.6277 (2)	0.8431 (4)	−0.03718 (14)	0.0666 (6)
C006	0.7195 (3)	0.6362 (5)	−0.01176 (19)	0.0813 (8)
C007	0.6326 (2)	0.5548 (4)	0.11513 (16)	0.0756 (7)
C200	0.7896 (2)	0.3042 (4)	0.10100 (17)	0.0693 (7)
N101	0.7884 (16)	0.541 (4)	−0.0208 (10)	0.063 (4)	0.200 (6)
O101	0.6038 (14)	0.417 (4)	0.2020 (9)	0.094 (5)	0.200 (6)
C101	0.8404 (11)	0.338 (3)	0.0372 (9)	0.078 (4)	0.200 (6)
C102	0.9404 (15)	0.181 (4)	0.0322 (13)	0.106 (5)	0.200 (6)
H102	0.9836	0.2016	−0.0106	0.127*	0.200 (6)
C103	0.968 (3)	−0.007 (9)	0.097 (2)	0.123 (8)	0.200 (6)
H103	1.0281	−0.1287	0.0934	0.148*	0.200 (6)
C104	0.911 (3)	−0.032 (8)	0.173 (3)	0.114 (10)	0.200 (6)
H104	0.9409	−0.1371	0.2192	0.137*	0.200 (6)
C105	0.8117 (13)	0.111 (3)	0.1683 (12)	0.083 (4)	0.200 (6)
H105	0.7613	0.0855	0.2064	0.099*	0.200 (6)
N201	0.6488 (4)	0.4076 (8)	0.1792 (3)	0.0699 (10)	0.800 (6)
O201	0.7984 (4)	0.5783 (10)	−0.0572 (2)	0.0878 (12)	0.800 (6)
C201	0.7477 (3)	0.2458 (6)	0.1729 (2)	0.0743 (11)	0.800 (6)
C202	0.8001 (3)	0.0458 (7)	0.2286 (3)	0.0929 (13)	0.800 (6)
H202	0.7729	0.0069	0.2781	0.111*	0.800 (6)
C203	0.8944 (6)	−0.0923 (13)	0.2072 (4)	0.108 (2)	0.800 (6)
H203	0.9290	−0.2333	0.2415	0.129*	0.800 (6)
C204	0.9373 (7)	−0.0248 (18)	0.1366 (4)	0.101 (2)	0.800 (6)
H204	1.0026	−0.1170	0.1256	0.121*	0.800 (6)
C205	0.8883 (4)	0.1750 (8)	0.0802 (3)	0.0882 (12)	0.800 (6)
H205	0.9185	0.2201	0.0324	0.106*	0.800 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N001	0.0893 (15)	0.0481 (11)	0.0891 (15)	0.0095 (10)	−0.0295 (12)	−0.0151 (11)
C001	0.0901 (17)	0.0603 (14)	0.0745 (16)	−0.0016 (13)	−0.0021 (13)	−0.0065 (12)
C002	0.1032 (18)	0.0560 (14)	0.0650 (14)	−0.0053 (13)	−0.0140 (13)	0.0030 (11)
C003	0.0831 (15)	0.0441 (11)	0.0615 (13)	−0.0027 (11)	−0.0162 (11)	−0.0044 (10)
C004	0.0774 (14)	0.0386 (10)	0.0597 (13)	−0.0043 (10)	−0.0203 (11)	−0.0062 (9)
C005	0.0775 (15)	0.0455 (12)	0.0685 (14)	0.0002 (10)	−0.0143 (12)	−0.0116 (10)
C006	0.092 (2)	0.0502 (14)	0.088 (2)	0.0008 (14)	−0.0277 (16)	−0.0121 (13)
C007	0.0964 (18)	0.0426 (12)	0.0735 (16)	−0.0035 (12)	−0.0312 (14)	−0.0018 (11)
C200	0.0779 (15)	0.0411 (11)	0.0775 (16)	0.0017 (11)	−0.0238 (13)	−0.0034 (11)
N101	0.055 (6)	0.070 (9)	0.069 (10)	0.004 (6)	0.029 (8)	−0.024 (8)
O101	0.112 (11)	0.100 (8)	0.076 (8)	0.027 (8)	0.029 (6)	0.042 (6)
C101	0.066 (7)	0.076 (9)	0.080 (8)	0.003 (6)	−0.023 (5)	−0.015 (7)
C102	0.097 (11)	0.093 (11)	0.119 (13)	0.035 (9)	−0.010 (8)	−0.027 (10)
C103	0.123 (18)	0.097 (14)	0.13 (2)	0.025 (14)	−0.026 (12)	−0.016 (15)
C104	0.096 (15)	0.051 (13)	0.19 (3)	0.022 (11)	−0.001 (18)	0.04 (2)
C105	0.078 (8)	0.043 (7)	0.108 (10)	−0.003 (6)	−0.045 (7)	0.023 (7)
N201	0.090 (3)	0.0495 (15)	0.062 (2)	−0.0071 (19)	−0.0145 (17)	0.0082 (15)
O201	0.094 (2)	0.090 (2)	0.080 (3)	0.0190 (16)	0.0145 (19)	−0.006 (2)
C201	0.086 (2)	0.0420 (17)	0.080 (2)	−0.0069 (17)	−0.0324 (17)	0.0043 (15)
C202	0.103 (3)	0.055 (2)	0.103 (3)	−0.0087 (18)	−0.040 (2)	0.0186 (19)
C203	0.107 (4)	0.052 (3)	0.139 (4)	−0.001 (3)	−0.059 (3)	0.016 (3)
C204	0.096 (6)	0.061 (3)	0.125 (7)	0.015 (4)	−0.051 (4)	−0.008 (5)
C205	0.091 (3)	0.065 (2)	0.097 (3)	0.012 (2)	−0.022 (2)	−0.012 (2)

Geometric parameters (Å, º)

N001—C007	1.383 (3)	C200—C205	1.408 (5)
N001—C200	1.388 (3)	C200—C105	1.427 (15)
N001—C006	1.394 (4)	N101—C101	1.43 (3)
C001—C005	1.374 (3)	C101—C102	1.41 (2)
C001—C002^i	1.399 (3)	C102—C103	1.39 (4)
C001—H001	0.9300	C102—H102	0.9300
C002—C003	1.382 (3)	C103—C104	1.50 (4)
C002—C001^i	1.399 (3)	C103—H103	0.9300
C002—H002	0.9300	C104—C105	1.35 (4)
C003—C004	1.404 (3)	C104—H104	0.9300
C003—C007	1.471 (3)	C105—H105	0.9300
C004—C005	1.414 (3)	N201—C201	1.420 (6)
C004—C004^i	1.419 (4)	C201—C202	1.397 (5)
C005—C006	1.481 (3)	C202—C203	1.387 (7)
C006—N101	0.963 (18)	C202—H202	0.9300
C006—O201	1.306 (5)	C203—C204	1.363 (8)
C007—N201	1.248 (5)	C203—H203	0.9300
C007—O101	1.641 (14)	C204—C205	1.389 (7)
C200—C101	1.286 (15)	C204—H204	0.9300
C200—C201	1.367 (4)	C205—H205	0.9300
C007—N001—C200	108.7 (2)	N001—C200—C105	144.3 (9)
C007—N001—C006	126.0 (2)	C006—N101—C101	120.6 (15)
C200—N001—C006	125.3 (3)	C200—C101—C102	118.6 (15)
C005—C001—C002^i	120.4 (3)	C200—C101—N101	114.3 (12)
C005—C001—H001	119.8	C102—C101—N101	127.1 (16)
C002^i—C001—H001	119.8	C103—C102—C101	114 (2)
C003—C002—C001^i	120.5 (2)	C103—C102—H102	123.1
C003—C002—H002	119.8	C101—C102—H102	123.1
C001^i—C002—H002	119.8	C102—C103—C104	126 (3)
C002—C003—C004	120.5 (2)	C102—C103—H103	116.8
C002—C003—C007	121.8 (2)	C104—C103—H103	116.8
C004—C003—C007	117.6 (2)	C105—C104—C103	114 (3)
C003—C004—C005	121.6 (2)	C105—C104—H104	122.8
C003—C004—C004^i	118.9 (3)	C103—C104—H104	122.8
C005—C004—C004^i	119.5 (3)	C104—C105—C200	115 (2)
C001—C005—C004	120.2 (2)	C104—C105—H105	122.4
C001—C005—C006	118.5 (3)	C200—C105—H105	122.4
C004—C005—C006	121.3 (2)	C007—N201—C201	105.7 (4)
N101—C006—N001	94.6 (11)	C200—C201—C202	120.8 (4)
O201—C006—N001	122.8 (3)	C200—C201—N201	111.2 (3)
N101—C006—C005	150.9 (11)	C202—C201—N201	128.0 (4)
O201—C006—C005	122.8 (3)	C203—C202—C201	117.2 (4)
N001—C006—C005	114.4 (3)	C203—C202—H202	121.4
N201—C007—N001	111.9 (3)	C201—C202—H202	121.4
N201—C007—C003	129.1 (3)	C204—C203—C202	121.1 (5)
N001—C007—C003	119.0 (2)	C204—C203—H203	119.4
N001—C007—O101	134.7 (6)	C202—C203—H203	119.4
C003—C007—O101	106.1 (6)	C203—C204—C205	123.2 (7)
C101—C200—N001	85.1 (6)	C203—C204—H204	118.4
C201—C200—N001	102.5 (3)	C205—C204—H204	118.4
C201—C200—C205	122.6 (3)	C204—C205—C200	115.0 (5)
N001—C200—C205	134.9 (3)	C204—C205—H205	122.5
C101—C200—C105	130.3 (10)	C200—C205—H205	122.5
C001^i—C002—C003—C004	1.2 (3)	C007—N001—C200—C105	7.6 (9)
C001^i—C002—C003—C007	−179.72 (19)	C006—N001—C200—C105	−173.1 (9)
C002—C003—C004—C005	179.48 (19)	O201—C006—N101—C101	−174 (4)
C007—C003—C004—C005	0.3 (3)	N001—C006—N101—C101	1.8 (17)
C002—C003—C004—C004^i	−0.9 (3)	C005—C006—N101—C101	178.9 (8)
C007—C003—C004—C004^i	179.9 (2)	N001—C200—C101—C102	179.1 (12)
C002^i—C001—C005—C004	−0.3 (3)	C205—C200—C101—C102	−0.7 (10)
C002^i—C001—C005—C006	179.90 (19)	C105—C200—C101—C102	−5.9 (16)
C003—C004—C005—C001	179.70 (19)	N001—C200—C101—N101	0.6 (11)
C004^i—C004—C005—C001	0.1 (3)	C205—C200—C101—N101	−179.2 (14)
C003—C004—C005—C006	−0.6 (3)	C105—C200—C101—N101	175.6 (11)
C004^i—C004—C005—C006	179.9 (2)	C006—N101—C101—C200	−2 (2)
C007—N001—C006—N101	177.7 (11)	C006—N101—C101—C102	179.6 (16)
C200—N001—C006—N101	−1.5 (11)	C200—C101—C102—C103	3 (3)
C007—N001—C006—O201	−179.7 (3)	N101—C101—C102—C103	−178 (3)
C200—N001—C006—O201	1.1 (4)	C101—C102—C103—C104	−7 (6)
C007—N001—C006—C005	−0.8 (3)	C102—C103—C104—C105	12 (8)
C200—N001—C006—C005	180.00 (18)	C103—C104—C105—C200	−12 (5)
C001—C005—C006—N101	4 (2)	C101—C200—C105—C104	11 (3)
C004—C005—C006—N101	−176 (2)	C201—C200—C105—C104	−167 (3)
C001—C005—C006—O201	−0.6 (4)	N001—C200—C105—C104	−178 (2)
C004—C005—C006—O201	179.6 (3)	C205—C200—C105—C104	7 (2)
C001—C005—C006—N001	−179.52 (19)	N001—C007—N201—C201	0.3 (3)
C004—C005—C006—N001	0.7 (3)	C003—C007—N201—C201	179.9 (2)
C200—N001—C007—N201	−0.4 (3)	O101—C007—N201—C201	172 (2)
C006—N001—C007—N201	−179.7 (2)	N001—C200—C201—C202	179.0 (2)
C200—N001—C007—C003	179.95 (17)	C205—C200—C201—C202	−1.9 (4)
C006—N001—C007—C003	0.6 (3)	C105—C200—C201—C202	5.4 (7)
C200—N001—C007—O101	−5.1 (9)	N001—C200—C201—N201	−0.1 (3)
C006—N001—C007—O101	175.6 (9)	C205—C200—C201—N201	179.0 (3)
C002—C003—C007—N201	0.9 (4)	C105—C200—C201—N201	−173.7 (8)
C004—C003—C007—N201	−180.0 (3)	C007—N201—C201—C200	−0.2 (3)
C002—C003—C007—N001	−179.5 (2)	C007—N201—C201—C202	−179.2 (3)
C004—C003—C007—N001	−0.4 (3)	C200—C201—C202—C203	−1.0 (5)
C002—C003—C007—O101	4.3 (7)	N201—C201—C202—C203	177.9 (4)
C004—C003—C007—O101	−176.6 (7)	C201—C202—C203—C204	3.2 (9)
C007—N001—C200—C101	−178.9 (5)	C202—C203—C204—C205	−2.6 (13)
C006—N001—C200—C101	0.4 (6)	C203—C204—C205—C200	−0.3 (11)
C007—N001—C200—C201	0.2 (2)	C101—C200—C205—C204	−178.4 (9)
C006—N001—C200—C201	179.6 (2)	C201—C200—C205—C204	2.5 (6)
C007—N001—C200—C205	−178.7 (3)	N001—C200—C205—C204	−178.7 (5)
C006—N001—C200—C205	0.7 (4)	C105—C200—C205—C204	−2.4 (7)

Symmetry code: (i) −x+1, −y+2, −z.

(solid_solution_293K_Mo)

Crystal data

C26H12N4O2	F(000) = 424
Mr = 412.40	Dx = 1.506 Mg m^−3 Dm = 1.549 Mg m^−3 Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 947 reflections
a = 11.7980 (16) Å	θ = 1.8–20.8°
b = 4.8049 (6) Å	µ = 0.10 mm^−1
c = 16.239 (2) Å	T = 293 K
β = 99.021 (2)°	Plate, brown
V = 909.2 (2) Å^3	0.3 × 0.06 × 0.02 mm
Z = 2

Data collection

Three-circle diffractometer with SIEMENS CCD detector	519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
Graphite monochromator	θmax = 20.8°, θmin = 1.8°
ω– and phi–scans, step width 0.3 deg.	h = −11→11
3103 measured reflections	k = −4→4
947 independent reflections	l = −16→16

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.175	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.3463P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
947 reflections	Δρmax = 0.15 e Å^−3
175 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

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	Occ. (<1)
C01	0.3745 (7)	0.3447 (12)	0.5360 (5)	0.072 (2)
C02	0.3742 (7)	0.4798 (14)	0.6108 (5)	0.083 (2)
C03	0.4577 (5)	0.3976 (11)	0.4863 (5)	0.0629 (19)
C04	0.4581 (7)	0.2611 (13)	0.4100 (5)	0.072 (2)
C05	0.5392 (7)	0.3182 (14)	0.3623 (5)	0.082 (2)
C06	0.2827 (8)	0.1381 (16)	0.5105 (6)	0.092 (3)
C07	0.3672 (7)	0.0533 (13)	0.3844 (6)	0.080 (2)
H02	0.310 (4)	0.440 (10)	0.647 (3)	0.07 (2)*
H05	0.549 (4)	0.245 (11)	0.305 (3)	0.08 (2)*
N1	0.2862 (6)	0.0035 (11)	0.4353 (5)	0.085 (2)
N2	0.3602 (6)	−0.0900 (12)	0.3169 (4)	0.099 (2)
O1	0.2048 (5)	0.0747 (11)	0.5519 (4)	0.118 (2)
C08	0.1954 (16)	−0.194 (3)	0.4118 (12)	0.041 (5)*	0.54 (2)
C09	0.2424 (17)	−0.263 (3)	0.3320 (14)	0.047 (5)*	0.54 (2)
C10	0.1882 (15)	−0.450 (3)	0.2842 (13)	0.067 (5)*	0.54 (2)
H10	0.2153	−0.4894	0.2347	0.100*	0.54 (2)
C11	0.0968 (15)	−0.592 (3)	0.2997 (17)	0.060 (5)*	0.54 (2)
H11	0.0623	−0.7271	0.2631	0.090*	0.54 (2)
C12	0.056 (3)	−0.529 (4)	0.3726 (17)	0.068 (7)*	0.54 (2)
H12	−0.0064	−0.6323	0.3849	0.102*	0.54 (2)
C13	0.101 (2)	−0.317 (6)	0.431 (2)	0.103 (11)*	0.54 (2)
H13	0.0682	−0.2693	0.4772	0.155*	0.54 (2)
C081	0.236 (2)	−0.211 (6)	0.388 (2)	0.026 (9)*	0.29 (2)
C091	0.281 (3)	−0.231 (6)	0.3102 (18)	0.049 (9)*	0.29 (2)
C101	0.224 (2)	−0.438 (4)	0.2538 (16)	0.051 (8)*	0.29 (2)
H101	0.2527	−0.4801	0.2051	0.077*	0.29 (2)
C111	0.131 (3)	−0.571 (6)	0.2713 (19)	0.064 (9)*	0.29 (2)
H111	0.0921	−0.6885	0.2307	0.096*	0.29 (2)
C121	0.091 (3)	−0.548 (6)	0.340 (3)	0.040 (9)*	0.29 (2)
H121	0.0340	−0.6752	0.3476	0.060*	0.29 (2)
C131	0.123 (3)	−0.339 (6)	0.410 (2)	0.041 (9)*	0.29 (2)
H131	0.0852	−0.2977	0.4550	0.062*	0.29 (2)
C082	0.208 (5)	−0.179 (10)	0.380 (4)	0.029 (16)*	0.17 (14)
C092	0.163 (4)	−0.153 (8)	0.471 (3)	0.073 (15)*	0.17 (14)
C102	0.054 (4)	−0.306 (8)	0.470 (3)	0.079 (14)*	0.17 (14)
H102	0.0109	−0.2747	0.5125	0.119*	0.17 (14)
C112	0.017 (3)	−0.491 (7)	0.409 (2)	0.045 (11)*	0.17 (14)
H112	−0.0395	−0.6189	0.4175	0.068*	0.17 (14)
C122	0.054 (7)	−0.495 (14)	0.347 (6)	0.08 (3)*	0.17 (14)
H122	0.0154	−0.5745	0.2986	0.124*	0.17 (14)
C132	0.170 (4)	−0.358 (8)	0.353 (3)	0.057 (13)*	0.17 (14)
H132	0.2202	−0.4602	0.3262	0.086*	0.17 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C01	0.097 (6)	0.040 (4)	0.068 (5)	−0.003 (4)	−0.018 (5)	0.002 (4)
C02	0.100 (6)	0.058 (5)	0.087 (6)	0.000 (5)	0.003 (5)	0.011 (5)
C03	0.080 (6)	0.044 (4)	0.059 (5)	0.001 (3)	−0.007 (4)	0.011 (4)
C04	0.102 (6)	0.047 (4)	0.060 (6)	0.012 (5)	−0.012 (4)	0.003 (4)
C05	0.114 (7)	0.060 (5)	0.065 (6)	0.004 (5)	−0.007 (5)	−0.001 (4)
C06	0.108 (7)	0.060 (6)	0.098 (8)	0.009 (6)	−0.016 (6)	0.018 (5)
C07	0.103 (6)	0.041 (5)	0.081 (6)	−0.002 (4)	−0.036 (6)	0.005 (5)
N1	0.104 (5)	0.051 (4)	0.085 (5)	−0.003 (4)	−0.026 (5)	0.016 (4)
N2	0.138 (6)	0.050 (3)	0.088 (5)	0.007 (4)	−0.048 (4)	−0.023 (3)
O1	0.122 (5)	0.092 (4)	0.134 (5)	−0.013 (4)	−0.007 (4)	0.017 (4)

Geometric parameters (Å, º)

C01—C02	1.378 (8)	C10—H10	0.9300
C01—C03	1.388 (8)	C11—C12	1.38 (3)
C01—C06	1.480 (9)	C11—H11	0.9300
C02—C05^i	1.426 (9)	C12—C13	1.44 (3)
C02—H02	1.05 (5)	C12—H12	0.9300
C03—C04	1.403 (8)	C13—H13	0.9300
C03—C03^i	1.422 (11)	C081—C091	1.45 (5)
C04—C05	1.351 (8)	C081—C131	1.56 (5)
C04—C07	1.476 (8)	C091—C101	1.44 (3)
C05—C02^i	1.426 (9)	C101—C111	1.34 (4)
C05—H05	1.02 (5)	C101—H101	0.9300
C06—O1	1.258 (8)	C111—C121	1.28 (6)
C06—N1	1.389 (9)	C111—H111	0.9300
C07—N2	1.285 (8)	C121—C131	1.53 (6)
C07—N1	1.378 (8)	C121—H121	0.9300
N1—C081	1.36 (3)	C131—H131	0.9300
N1—C08	1.438 (17)	C082—C132	1.03 (5)
N1—C082	1.47 (5)	C082—C092	1.65 (8)
N1—C092	1.81 (5)	C092—C102	1.47 (6)
N2—C091	1.15 (4)	C102—C112	1.35 (5)
N2—C09	1.67 (2)	C102—H102	0.9300
O1—C092	1.72 (4)	C112—C122	1.16 (12)
C08—C13	1.34 (3)	C112—H112	0.9300
C08—C09	1.52 (3)	C122—C132	1.51 (8)
C09—C10	1.29 (2)	C122—H122	0.9300
C10—C11	1.33 (2)	C132—H132	0.9300
C02—C01—C03	121.7 (7)	C11—C12—C13	125 (2)
C02—C01—C06	117.4 (9)	C11—C12—H12	117.6
C03—C01—C06	120.9 (7)	C13—C12—H12	117.6
C01—C02—C05^i	119.3 (8)	C08—C13—C12	114 (2)
C01—C02—H02	121 (3)	C08—C13—H13	123.2
C05^i—C02—H02	120 (3)	C12—C13—H13	123.2
C01—C03—C04	121.9 (6)	N1—C081—C091	111 (2)
C01—C03—C03^i	118.1 (9)	N1—C081—C131	119 (3)
C04—C03—C03^i	120.0 (9)	C091—C081—C131	128 (3)
C05—C04—C03	120.8 (7)	N2—C091—C101	139 (3)
C05—C04—C07	121.6 (8)	N2—C091—C081	106 (3)
C03—C04—C07	117.5 (8)	C101—C091—C081	114 (3)
C04—C05—C02^i	120.0 (8)	C111—C101—C091	121 (3)
C04—C05—H05	130 (3)	C111—C101—H101	119.7
C02^i—C05—H05	110 (3)	C091—C101—H101	119.7
O1—C06—N1	118.9 (9)	C121—C111—C101	125 (3)
O1—C06—C01	125.2 (9)	C121—C111—H111	117.7
N1—C06—C01	115.9 (8)	C101—C111—H111	117.7
N2—C07—N1	117.4 (8)	C111—C121—C131	129 (3)
N2—C07—C04	123.3 (11)	C111—C121—H121	115.6
N1—C07—C04	119.3 (8)	C131—C121—H121	115.6
C081—N1—C07	94.3 (16)	C121—C131—C081	102 (3)
C081—N1—C06	140.9 (18)	C121—C131—H131	129.0
C07—N1—C06	124.5 (7)	C081—C131—H131	129.0
C07—N1—C08	120.9 (10)	C132—C082—N1	160 (5)
C06—N1—C08	114.6 (11)	C132—C082—C092	105 (6)
C07—N1—C082	99 (3)	N1—C082—C092	71 (3)
C06—N1—C082	135 (3)	C102—C092—C082	111 (4)
C091—N2—C07	109.8 (17)	C102—C092—O1	118 (3)
C07—N2—C09	94.9 (8)	C082—C092—O1	129 (3)
C06—O1—C092	83.9 (16)	C112—C102—C092	121 (4)
C13—C08—N1	147 (2)	C112—C102—H102	119.5
C13—C08—C09	122 (2)	C092—C102—H102	119.5
N1—C08—C09	90.8 (14)	C122—C112—C102	122 (4)
C10—C09—C08	116.8 (17)	C122—C112—H112	119.2
C10—C09—N2	127 (2)	C102—C112—H112	119.2
C08—C09—N2	116.0 (13)	C112—C122—C132	113 (6)
C09—C10—C11	126 (2)	C112—C122—H122	123.3
C09—C10—H10	117.2	C132—C122—H122	123.3
C11—C10—H10	117.2	C082—C132—C122	136 (7)
C10—C11—C12	117 (2)	C082—C132—H132	112.1
C10—C11—H11	121.5	C122—C132—H132	112.1
C12—C11—H11	121.5
C03—C01—C02—C05^i	0.7 (9)	C06—N1—C081—C131	14 (4)
C06—C01—C02—C05^i	−179.6 (5)	C08—N1—C081—C131	−5 (2)
C02—C01—C03—C04	−179.8 (5)	C082—N1—C081—C131	−61 (14)
C06—C01—C03—C04	0.6 (8)	C092—N1—C081—C131	5 (2)
C02—C01—C03—C03^i	−1.5 (9)	C06—N1—C081—C07	−173.0 (18)
C06—C01—C03—C03^i	178.8 (6)	C08—N1—C081—C07	167 (3)
C01—C03—C04—C05	179.3 (6)	C082—N1—C081—C07	112 (15)
C03^i—C03—C04—C05	1.1 (9)	C092—N1—C081—C07	178.1 (13)
C01—C03—C04—C07	−1.0 (7)	N2—C07—C081—N1	−175.8 (12)
C03^i—C03—C04—C07	−179.2 (6)	C04—C07—C081—N1	16 (4)
C03—C04—C05—C02^i	−0.2 (9)	C091—C07—C081—N1	−171 (2)
C07—C04—C05—C02^i	−180.0 (5)	N2—C07—C081—C091	−5.1 (11)
C02—C01—C06—O1	−0.5 (9)	N1—C07—C081—C091	171 (2)
C03—C01—C06—O1	179.2 (7)	C04—C07—C081—C091	−173 (2)
C02—C01—C06—N1	−179.3 (5)	N2—C07—C081—C131	−156 (7)
C03—C01—C06—N1	0.3 (8)	N1—C07—C081—C131	20 (6)
C05—C04—C07—N2	1.5 (9)	C04—C07—C081—C131	36 (9)
C03—C04—C07—N2	−178.3 (5)	C091—C07—C081—C131	−151 (8)
C05—C04—C07—N1	−179.8 (6)	C07—N2—C091—C101	−179 (3)
C03—C04—C07—N1	0.5 (7)	C09—N2—C091—C101	−172 (8)
C05—C04—C07—C091	−1 (2)	C07—N2—C091—C081	−9 (2)
C03—C04—C07—C091	179.2 (18)	C09—N2—C091—C081	−3 (4)
C05—C04—C07—C081	168 (3)	C09—N2—C091—C07	6 (6)
C03—C04—C07—C081	−12 (3)	N1—C081—C091—N2	13 (3)
N2—C07—N1—C081	4.6 (13)	C131—C081—C091—N2	174 (2)
C04—C07—N1—C081	−174.2 (13)	C07—C081—C091—N2	5.8 (13)
C091—C07—N1—C081	6.3 (14)	N1—C081—C091—C101	−174.7 (19)
N2—C07—N1—C06	179.2 (5)	C131—C081—C091—C101	−13 (4)
C04—C07—N1—C06	0.4 (8)	C07—C081—C091—C101	178.4 (19)
C091—C07—N1—C06	−179.0 (8)	N1—C081—C091—C07	6.8 (14)
C081—C07—N1—C06	174.7 (14)	C131—C081—C091—C07	168 (3)
N2—C07—N1—C08	−2.1 (10)	N1—C07—C091—N2	−177.2 (12)
C04—C07—N1—C08	179.1 (8)	C04—C07—C091—N2	4 (3)
C091—C07—N1—C08	−0.4 (10)	C081—C07—C091—N2	−171 (2)
C081—C07—N1—C08	−6.7 (16)	N2—C07—C091—C081	171 (2)
N2—C07—N1—C082	−9 (2)	N1—C07—C091—C081	−6.3 (13)
C04—C07—N1—C082	172 (2)	C04—C07—C091—C081	174.8 (17)
C091—C07—N1—C082	−7 (2)	N2—C091—C101—C111	177 (3)
C081—C07—N1—C082	−14 (2)	C081—C091—C101—C111	7 (3)
N2—C07—N1—C092	0 (3)	C091—C101—C111—C121	−7 (3)
C04—C07—N1—C092	−179 (3)	C101—C111—C121—C131	11 (4)
C091—C07—N1—C092	2 (3)	C111—C121—C131—C081	−13 (4)
C081—C07—N1—C092	−5 (3)	N1—C081—C131—C121	175 (2)
O1—C06—N1—C081	−8 (2)	C091—C081—C131—C121	15 (4)
C01—C06—N1—C081	171 (2)	C07—C081—C131—C121	159 (6)
C092—C06—N1—C081	−8 (2)	C081—N1—C082—C132	26 (13)
O1—C06—N1—C07	−179.7 (6)	C07—N1—C082—C132	96 (22)
C01—C06—N1—C07	−0.8 (8)	C06—N1—C082—C132	−94 (22)
C092—C06—N1—C07	−179.8 (12)	C08—N1—C082—C132	−68 (19)
O1—C06—N1—C08	1.5 (10)	C092—N1—C082—C132	−81 (22)
C01—C06—N1—C08	−179.6 (8)	C081—N1—C082—C092	106 (15)
C092—C06—N1—C08	1.5 (14)	C07—N1—C082—C092	176.2 (14)
O1—C06—N1—C082	12 (3)	C06—N1—C082—C092	−14 (3)
C01—C06—N1—C082	−169 (3)	C08—N1—C082—C092	12 (5)
C092—C06—N1—C082	12 (3)	C132—C082—C092—C102	−23 (5)
O1—C06—N1—C092	0.0 (13)	N1—C082—C092—C102	177 (3)
C01—C06—N1—C092	178.9 (12)	C132—C082—C092—O1	172 (4)
N1—C07—N2—C091	3.2 (14)	N1—C082—C092—O1	12 (3)
C04—C07—N2—C091	−178.1 (13)	C132—C082—C092—N1	160 (5)
C081—C07—N2—C091	6.4 (15)	C132—C082—C092—C06	166 (4)
N1—C07—N2—C09	1.5 (7)	N1—C082—C092—C06	6.5 (16)
C04—C07—N2—C09	−179.7 (6)	C06—O1—C092—C102	−173 (3)
C091—C07—N2—C09	−1.7 (15)	C06—O1—C092—C082	−10 (3)
C081—C07—N2—C09	4.7 (10)	C06—O1—C092—N1	0.0 (9)
N1—C06—O1—C092	0.0 (13)	C081—N1—C092—C102	−24 (8)
C01—C06—O1—C092	−178.8 (12)	C07—N1—C092—C102	−19 (10)
C081—N1—C08—C13	167 (5)	C06—N1—C092—C102	162 (8)
C07—N1—C08—C13	−178 (2)	C08—N1—C092—C102	−16 (7)
C06—N1—C08—C13	1 (3)	C082—N1—C092—C102	−8 (8)
C082—N1—C08—C13	−160 (8)	C081—N1—C092—C082	−15 (3)
C092—N1—C08—C13	3 (3)	C07—N1—C092—C082	−10 (4)
C081—N1—C08—C09	−13 (3)	C06—N1—C092—C082	170 (2)
C07—N1—C08—C09	1.1 (12)	C08—N1—C092—C082	−8 (3)
C06—N1—C08—C09	179.9 (7)	C081—N1—C092—O1	174.2 (19)
C082—N1—C08—C09	19 (6)	C07—N1—C092—O1	179 (2)
C092—N1—C08—C09	−178 (2)	C06—N1—C092—O1	0.0 (8)
C13—C08—C09—C10	−1 (2)	C08—N1—C092—O1	−178 (3)
N1—C08—C09—C10	179.0 (11)	C082—N1—C092—O1	−170 (3)
C13—C08—C09—N2	179.4 (14)	C081—N1—C092—C06	174.3 (15)
N1—C08—C09—N2	−0.1 (12)	C07—N1—C092—C06	179 (3)
C091—N2—C09—C10	6 (5)	C08—N1—C092—C06	−178 (2)
C07—N2—C09—C10	−179.8 (13)	C082—N1—C092—C06	−170 (2)
C091—N2—C09—C08	−175 (6)	O1—C06—C092—C102	14 (6)
C07—N2—C09—C08	−0.8 (11)	N1—C06—C092—C102	−166 (7)
C08—C09—C10—C11	−2 (2)	O1—C06—C092—C082	173 (2)
N2—C09—C10—C11	177.3 (10)	N1—C06—C092—C082	−7.4 (18)
C09—C10—C11—C12	1 (2)	N1—C06—C092—O1	180.0 (13)
C10—C11—C12—C13	2 (3)	O1—C06—C092—N1	−180.0 (13)
N1—C08—C13—C12	−176 (2)	C082—C092—C102—C112	14 (4)
C09—C08—C13—C12	4 (3)	O1—C092—C102—C112	−179 (3)
C11—C12—C13—C08	−5 (3)	N1—C092—C102—C112	21 (10)
C07—N1—C081—C091	−9.3 (19)	C06—C092—C102—C112	171 (5)
C06—N1—C081—C091	177.7 (11)	C092—C102—C112—C122	−17 (6)
C08—N1—C081—C091	158 (5)	C102—C112—C122—C132	21 (7)
C082—N1—C081—C091	102 (16)	N1—C082—C132—C122	115 (20)
C092—N1—C081—C091	169 (3)	C092—C082—C132—C122	40 (8)
C07—N1—C081—C131	−173 (2)	C112—C122—C132—C082	−43 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.