Structural comparisons of isomeric series of 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines

The structures of three new 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines, 8-methyl-7-(4-chlorophenyl)-10-phenyl-6,10-di­hydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, C₂₇H₂₀ClN₃, 8-methyl-7-(3-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo­[b]pyrazolo[3,4-b]quinoline, C₂₆H₂₀N₄, and 8-methyl-7-(4-pyridinyl)-10-phenyl-10H-benzo[h]pyrazolo[3,4-b]quinoline, C₂₆H₁₈N₄, which is an unexpected oxidation product isolated from the attempted synthesis of 8-methyl-7-(4-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, and those of three new 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines, 11-(4-methylphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C₂₈H₂₃N₃ (, Z′ = 2), 11-(4-methoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C₂₈H₂₃N₃O (P2₁/c, Z′ = 4), and 11-(3,4,5-tri­methoxyphenyl)-10-methyl-8-phenyl-6,8-di­hydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C₃₀H₂₇N₃O₃, are reported. The crystal structures are compared with those of a number of analogues reported in the recent literature; in particular, structural comparisons are drawn within each series as the substituted pendent aryl group is varied, and between several pairs of strictly isomeric 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines containing the same aryl substituents within each pair. Intermolecular interactions of the C—H...π type are found in the crystal structures of both series, but π...π stacking interactions are found only in the 7-aryl-benzo[h]pyrazolo[3,4-b]quinoline series.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003 & SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 & PRPKAPPA (Ferguson, 1999).

Figures

In full text version

(IV) 8-methyl-7-(4-chlorophenyl)-10-phenyl-6,10-dihydro- 5H-benzo[h]pyrazolo[3,4-b]quinoline

Crystal data

C27H20ClN3	F(000) = 880
Mr = 421.91	Dx = 1.352 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4752 reflections
a = 12.1072 (4) Å	θ = 2.3–27.5°
b = 14.2672 (5) Å	µ = 0.21 mm^−1
c = 12.7635 (4) Å	T = 120 K
β = 109.953 (8)°	Lath, colourless
V = 2072.37 (16) Å^3	0.38 × 0.38 × 0.10 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	4752 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
ϕ & ω scans	h = −15→15
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −18→18
Tmin = 0.936, Tmax = 0.980	l = −16→16
23840 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.6125P] where P = (Fo^2 + 2Fc^2)/3
4752 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.00744 (18)	0.36013 (13)	−0.16474 (15)	0.0294 (4)
C2	0.03741 (19)	0.36595 (13)	−0.25987 (16)	0.0329 (5)
C3	0.14616 (19)	0.40119 (14)	−0.25367 (16)	0.0352 (5)
C4	0.22395 (18)	0.43202 (15)	−0.15249 (16)	0.0344 (5)
C4A	0.19546 (17)	0.42682 (13)	−0.05568 (15)	0.0284 (4)
C5	0.27633 (18)	0.46297 (16)	0.05400 (17)	0.0372 (5)
C6	0.26683 (19)	0.40943 (17)	0.14916 (17)	0.0421 (5)
C6A	0.14236 (16)	0.39944 (13)	0.14617 (15)	0.0283 (4)
C7	0.11145 (17)	0.39896 (13)	0.24182 (15)	0.0260 (4)
C71	0.19864 (16)	0.41941 (13)	0.35436 (15)	0.0266 (4)
C72	0.23025 (17)	0.35070 (14)	0.43661 (15)	0.0301 (4)
C73	0.30911 (18)	0.36985 (14)	0.54142 (16)	0.0332 (5)
C74	0.35735 (17)	0.45859 (15)	0.56445 (15)	0.0318 (5)
Cl74	0.45535 (5)	0.48281 (5)	0.69740 (4)	0.04818 (19)
C75	0.32950 (18)	0.52784 (14)	0.48396 (16)	0.0348 (5)
C76	0.24985 (18)	0.50754 (14)	0.37932 (16)	0.0324 (5)
C7A	−0.00574 (16)	0.37700 (12)	0.22819 (14)	0.0234 (4)
C8	−0.07678 (16)	0.36835 (12)	0.29704 (15)	0.0257 (4)
C81	−0.04571 (18)	0.38328 (14)	0.41953 (15)	0.0314 (5)
N9	−0.18497 (14)	0.34299 (11)	0.23761 (12)	0.0284 (4)
N10	−0.18927 (13)	0.33480 (11)	0.12828 (12)	0.0267 (4)
C101	−0.29791 (16)	0.31238 (13)	0.04437 (15)	0.0263 (4)
C102	−0.40149 (17)	0.32705 (14)	0.06538 (16)	0.0326 (5)
C103	−0.50762 (18)	0.30409 (16)	−0.01550 (16)	0.0379 (5)
C104	−0.51116 (19)	0.26809 (16)	−0.11708 (17)	0.0398 (5)
C105	−0.40778 (19)	0.25512 (15)	−0.13796 (17)	0.0390 (5)
C106	−0.30061 (17)	0.27617 (14)	−0.05773 (16)	0.0321 (5)
C10A	−0.08189 (16)	0.35651 (12)	0.12001 (14)	0.0240 (4)
N11	−0.05666 (13)	0.36025 (10)	0.02614 (12)	0.0245 (3)
C11A	0.05456 (16)	0.38283 (12)	0.04048 (15)	0.0241 (4)
C11B	0.08613 (16)	0.38955 (12)	−0.06186 (15)	0.0250 (4)
H1	−0.0672	0.3360	−0.1694	0.035*
H2	−0.0165	0.3458	−0.3295	0.039*
H3	0.1673	0.4042	−0.3188	0.042*
H4	0.2978	0.4571	−0.1490	0.041*
H5A	0.3583	0.4598	0.0549	0.045*
H5B	0.2577	0.5296	0.0620	0.045*
H6A	0.3136	0.4412	0.2192	0.050*
H6B	0.3008	0.3463	0.1494	0.050*
H72	0.1971	0.2898	0.4204	0.036*
H73	0.3300	0.3226	0.5972	0.040*
H75	0.3643	0.5882	0.5001	0.042*
H76	0.2298	0.5548	0.3235	0.039*
H81A	−0.1174	0.3954	0.4367	0.047*
H81B	0.0074	0.4371	0.4428	0.047*
H81C	−0.0068	0.3271	0.4595	0.047*
H102	−0.3998	0.3526	0.1346	0.039*
H103	−0.5788	0.3132	−0.0010	0.045*
H104	−0.5843	0.2524	−0.1721	0.048*
H105	−0.4101	0.2314	−0.2083	0.047*
H106	−0.2296	0.2660	−0.0722	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0334 (11)	0.0296 (10)	0.0257 (10)	−0.0030 (8)	0.0109 (9)	−0.0014 (8)
C2	0.0429 (13)	0.0330 (11)	0.0233 (10)	0.0018 (9)	0.0121 (9)	−0.0001 (8)
C3	0.0449 (13)	0.0385 (11)	0.0293 (10)	0.0067 (10)	0.0220 (10)	0.0053 (9)
C4	0.0300 (11)	0.0423 (12)	0.0350 (11)	0.0028 (9)	0.0165 (9)	0.0060 (9)
C4A	0.0273 (10)	0.0303 (10)	0.0303 (10)	0.0040 (8)	0.0132 (8)	0.0029 (8)
C5	0.0285 (12)	0.0497 (13)	0.0354 (11)	−0.0056 (10)	0.0135 (9)	0.0019 (9)
C6	0.0308 (12)	0.0638 (15)	0.0326 (11)	−0.0105 (11)	0.0122 (9)	−0.0069 (10)
C6A	0.0249 (10)	0.0345 (10)	0.0253 (9)	−0.0026 (8)	0.0083 (8)	−0.0023 (8)
C7	0.0271 (11)	0.0264 (9)	0.0234 (9)	−0.0007 (8)	0.0071 (8)	−0.0012 (7)
C71	0.0210 (10)	0.0347 (11)	0.0247 (9)	−0.0020 (8)	0.0086 (8)	−0.0022 (8)
C72	0.0289 (11)	0.0319 (10)	0.0291 (10)	−0.0030 (8)	0.0094 (8)	−0.0022 (8)
C73	0.0321 (11)	0.0400 (12)	0.0274 (10)	0.0012 (9)	0.0099 (9)	0.0049 (9)
C74	0.0213 (10)	0.0506 (13)	0.0223 (9)	−0.0039 (9)	0.0060 (8)	−0.0033 (9)
Cl74	0.0384 (3)	0.0722 (4)	0.0264 (3)	−0.0131 (3)	0.0014 (2)	−0.0056 (3)
C75	0.0320 (12)	0.0375 (11)	0.0328 (11)	−0.0088 (9)	0.0084 (9)	−0.0065 (9)
C76	0.0320 (12)	0.0348 (11)	0.0280 (10)	−0.0024 (9)	0.0072 (9)	0.0015 (8)
C7A	0.0250 (10)	0.0230 (9)	0.0222 (9)	0.0000 (8)	0.0078 (8)	0.0006 (7)
C8	0.0274 (11)	0.0262 (9)	0.0241 (9)	−0.0005 (8)	0.0094 (8)	−0.0005 (7)
C81	0.0310 (11)	0.0404 (12)	0.0241 (10)	−0.0052 (9)	0.0109 (8)	−0.0034 (8)
N9	0.0301 (9)	0.0347 (9)	0.0224 (8)	−0.0015 (7)	0.0114 (7)	−0.0005 (7)
N10	0.0233 (9)	0.0360 (9)	0.0217 (8)	−0.0041 (7)	0.0086 (7)	−0.0008 (7)
C101	0.0240 (10)	0.0293 (10)	0.0237 (9)	−0.0039 (8)	0.0055 (8)	0.0026 (8)
C102	0.0280 (11)	0.0443 (12)	0.0267 (10)	−0.0027 (9)	0.0110 (9)	0.0018 (9)
C103	0.0241 (11)	0.0541 (13)	0.0345 (11)	−0.0026 (10)	0.0088 (9)	0.0056 (10)
C104	0.0276 (12)	0.0521 (14)	0.0327 (11)	−0.0077 (10)	0.0014 (9)	0.0000 (10)
C105	0.0382 (13)	0.0469 (13)	0.0291 (11)	−0.0078 (10)	0.0082 (9)	−0.0066 (9)
C106	0.0262 (11)	0.0384 (11)	0.0316 (11)	−0.0032 (9)	0.0099 (9)	−0.0050 (9)
C10A	0.0247 (10)	0.0255 (9)	0.0230 (9)	−0.0007 (8)	0.0098 (8)	−0.0001 (7)
N11	0.0240 (8)	0.0261 (8)	0.0239 (8)	0.0004 (7)	0.0089 (6)	0.0000 (6)
C11A	0.0250 (10)	0.0220 (9)	0.0264 (9)	0.0007 (8)	0.0104 (8)	0.0000 (7)
C11B	0.0293 (11)	0.0226 (9)	0.0256 (9)	0.0025 (8)	0.0126 (8)	−0.0002 (7)

Geometric parameters (Å, º)

C1—C2	1.383 (3)	C74—Cl74	1.7415 (19)
C1—C11B	1.398 (3)	C75—C76	1.385 (3)
C1—H1	0.95	C75—H75	0.95
C2—C3	1.386 (3)	C76—H76	0.95
C2—H2	0.95	C7A—C10A	1.405 (2)
C3—C4	1.385 (3)	C7A—C8	1.429 (2)
C3—H3	0.95	C8—N9	1.321 (2)
C4—C4A	1.394 (3)	C8—C81	1.493 (2)
C4—H4	0.95	C81—H81A	0.98
C4A—C11B	1.404 (3)	C81—H81B	0.98
C4A—C5	1.500 (3)	C81—H81C	0.98
C5—C6	1.472 (3)	N9—N10	1.384 (2)
C5—H5A	0.99	N10—C10A	1.375 (2)
C5—H5B	0.99	N10—C101	1.420 (2)
C6—C6A	1.501 (3)	C101—C102	1.385 (3)
C6—H6A	0.99	C101—C106	1.392 (3)
C6—H6B	0.99	C102—C103	1.385 (3)
C6A—C7	1.394 (2)	C102—H102	0.95
C6A—C11A	1.424 (3)	C103—C104	1.381 (3)
C7—C7A	1.405 (3)	C103—H103	0.95
C7—C71	1.493 (2)	C104—C105	1.378 (3)
C71—C76	1.390 (3)	C104—H104	0.95
C71—C72	1.391 (3)	C105—C106	1.384 (3)
C72—C73	1.380 (3)	C105—H105	0.95
C72—H72	0.95	C106—H106	0.95
C73—C74	1.383 (3)	C10A—N11	1.335 (2)
C73—H73	0.95	N11—C11A	1.335 (2)
C74—C75	1.382 (3)	C11A—C11B	1.484 (2)
C2—C1—C11B	120.51 (19)	C75—C76—C71	121.29 (18)
C2—C1—H1	119.7	C75—C76—H76	119.4
C11B—C1—H1	119.7	C71—C76—H76	119.4
C1—C2—C3	120.01 (18)	C10A—C7A—C7	117.68 (16)
C1—C2—H2	120.0	C10A—C7A—C8	104.81 (16)
C3—C2—H2	120.0	C7—C7A—C8	137.51 (17)
C4—C3—C2	119.92 (18)	N9—C8—C7A	110.95 (16)
C4—C3—H3	120.0	N9—C8—C81	119.12 (17)
C2—C3—H3	120.0	C7A—C8—C81	129.93 (17)
C3—C4—C4A	120.97 (19)	C8—C81—H81A	109.5
C3—C4—H4	119.5	C8—C81—H81B	109.5
C4A—C4—H4	119.5	H81A—C81—H81B	109.5
C4—C4A—C11B	118.97 (18)	C8—C81—H81C	109.5
C4—C4A—C5	121.94 (18)	H81A—C81—H81C	109.5
C11B—C4A—C5	119.05 (16)	H81B—C81—H81C	109.5
C6—C5—C4A	112.45 (18)	C8—N9—N10	106.92 (15)
C6—C5—H5A	109.1	C10A—N10—N9	110.31 (14)
C4A—C5—H5A	109.1	C10A—N10—C101	130.49 (15)
C6—C5—H5B	109.1	N9—N10—C101	119.07 (15)
C4A—C5—H5B	109.1	C102—C101—C106	120.26 (17)
H5A—C5—H5B	107.8	C102—C101—N10	119.12 (16)
C5—C6—C6A	112.87 (18)	C106—C101—N10	120.62 (17)
C5—C6—H6A	109.0	C101—C102—C103	119.40 (18)
C6A—C6—H6A	109.0	C101—C102—H102	120.3
C5—C6—H6B	109.0	C103—C102—H102	120.3
C6A—C6—H6B	109.0	C104—C103—C102	120.7 (2)
H6A—C6—H6B	107.8	C104—C103—H103	119.6
C7—C6A—C11A	119.49 (17)	C102—C103—H103	119.6
C7—C6A—C6	123.06 (17)	C105—C104—C103	119.47 (19)
C11A—C6A—C6	117.28 (16)	C105—C104—H104	120.3
C6A—C7—C7A	117.03 (16)	C103—C104—H104	120.3
C6A—C7—C71	121.93 (17)	C104—C105—C106	120.78 (19)
C7A—C7—C71	121.03 (16)	C104—C105—H105	119.6
C76—C71—C72	118.57 (17)	C106—C105—H105	119.6
C76—C71—C7	120.73 (17)	C105—C106—C101	119.33 (19)
C72—C71—C7	120.70 (17)	C105—C106—H106	120.3
C73—C72—C71	120.88 (18)	C101—C106—H106	120.3
C73—C72—H72	119.6	N11—C10A—N10	126.14 (16)
C71—C72—H72	119.6	N11—C10A—C7A	126.84 (17)
C72—C73—C74	119.31 (18)	N10—C10A—C7A	106.98 (15)
C72—C73—H73	120.3	C10A—N11—C11A	114.56 (15)
C74—C73—H73	120.3	N11—C11A—C6A	124.20 (16)
C75—C74—C73	121.22 (18)	N11—C11A—C11B	116.46 (16)
C75—C74—Cl74	119.66 (16)	C6A—C11A—C11B	119.33 (16)
C73—C74—Cl74	119.12 (15)	C1—C11B—C4A	119.60 (17)
C74—C75—C76	118.71 (18)	C1—C11B—C11A	120.64 (17)
C74—C75—H75	120.6	C4A—C11B—C11A	119.76 (16)
C76—C75—H75	120.6
C11B—C1—C2—C3	0.0 (3)	C8—N9—N10—C101	−177.04 (16)
C1—C2—C3—C4	−1.1 (3)	C10A—N10—C101—C102	−156.04 (19)
C2—C3—C4—C4A	1.1 (3)	N9—N10—C101—C102	19.5 (3)
C3—C4—C4A—C11B	0.1 (3)	C10A—N10—C101—C106	23.9 (3)
C3—C4—C4A—C5	−177.72 (19)	N9—N10—C101—C106	−160.51 (17)
C4—C4A—C5—C6	−148.6 (2)	C106—C101—C102—C103	0.9 (3)
C11B—C4A—C5—C6	33.6 (3)	N10—C101—C102—C103	−179.09 (18)
C4A—C5—C6—C6A	−51.1 (3)	C101—C102—C103—C104	−0.9 (3)
C5—C6—C6A—C7	−145.1 (2)	C102—C103—C104—C105	−0.1 (3)
C5—C6—C6A—C11A	39.7 (3)	C103—C104—C105—C106	1.1 (3)
C11A—C6A—C7—C7A	3.2 (3)	C104—C105—C106—C101	−1.1 (3)
C6—C6A—C7—C7A	−171.97 (19)	C102—C101—C106—C105	0.1 (3)
C11A—C6A—C7—C71	−177.70 (17)	N10—C101—C106—C105	−179.90 (18)
C6—C6A—C7—C71	7.2 (3)	N9—N10—C10A—N11	−176.53 (16)
C6A—C7—C71—C76	65.2 (3)	C101—N10—C10A—N11	−0.7 (3)
C7A—C7—C71—C76	−115.7 (2)	N9—N10—C10A—C7A	1.47 (19)
C6A—C7—C71—C72	−114.9 (2)	C101—N10—C10A—C7A	177.33 (18)
C7A—C7—C71—C72	64.2 (2)	C7—C7A—C10A—N11	−3.8 (3)
C76—C71—C72—C73	1.1 (3)	C8—C7A—C10A—N11	176.34 (17)
C7—C71—C72—C73	−178.73 (17)	C7—C7A—C10A—N10	178.26 (16)
C71—C72—C73—C74	−0.2 (3)	C8—C7A—C10A—N10	−1.65 (19)
C72—C73—C74—C75	−1.1 (3)	N10—C10A—N11—C11A	−179.83 (17)
C72—C73—C74—Cl74	179.17 (15)	C7A—C10A—N11—C11A	2.6 (3)
C73—C74—C75—C76	1.3 (3)	C10A—N11—C11A—C6A	1.7 (2)
Cl74—C74—C75—C76	−178.93 (15)	C10A—N11—C11A—C11B	−178.91 (15)
C74—C75—C76—C71	−0.3 (3)	C7—C6A—C11A—N11	−4.6 (3)
C72—C71—C76—C75	−0.9 (3)	C6—C6A—C11A—N11	170.78 (18)
C7—C71—C76—C75	178.99 (18)	C7—C6A—C11A—C11B	176.02 (16)
C6A—C7—C7A—C10A	0.6 (2)	C6—C6A—C11A—C11B	−8.6 (3)
C71—C7—C7A—C10A	−178.58 (16)	C2—C1—C11B—C4A	1.2 (3)
C6A—C7—C7A—C8	−179.6 (2)	C2—C1—C11B—C11A	−179.60 (17)
C71—C7—C7A—C8	1.3 (3)	C4—C4A—C11B—C1	−1.2 (3)
C10A—C7A—C8—N9	1.3 (2)	C5—C4A—C11B—C1	176.68 (17)
C7—C7A—C8—N9	−178.6 (2)	C4—C4A—C11B—C11A	179.57 (17)
C10A—C7A—C8—C81	−178.79 (18)	C5—C4A—C11B—C11A	−2.6 (3)
C7—C7A—C8—C81	1.3 (4)	N11—C11A—C11B—C1	−9.1 (2)
C7A—C8—N9—N10	−0.4 (2)	C6A—C11A—C11B—C1	170.34 (17)
C81—C8—N9—N10	179.66 (15)	N11—C11A—C11B—C4A	170.16 (17)
C8—N9—N10—C10A	−0.64 (19)	C6A—C11A—C11B—C4A	−10.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C72—H72···Cg1^i	0.95	2.88	3.823 (2)	170
C75—H75···Cg2^ii	0.95	2.94	3.860 (2)	164

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2.

(V) 8-methyl-7-(3-pyridinyl)-10-phenyl-6,10- dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline

Crystal data

C26H20N4	F(000) = 816
Mr = 388.46	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4456 reflections
a = 11.2274 (6) Å	θ = 3.0–27.5°
b = 13.7079 (8) Å	µ = 0.08 mm^−1
c = 12.6935 (7) Å	T = 120 K
β = 95.731 (3)°	Plate, colourless
V = 1943.82 (19) Å^3	0.12 × 0.10 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	4456 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2654 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ & ω scans	h = −14→14
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −17→17
Tmin = 0.987, Tmax = 0.998	l = −16→16
19684 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.9505P] where P = (Fo^2 + 2Fc^2)/3
4456 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.4652 (2)	0.36294 (16)	0.28142 (19)	0.0278 (6)
C2	0.4340 (2)	0.35731 (17)	0.1738 (2)	0.0311 (6)
C3	0.3149 (2)	0.36973 (18)	0.1334 (2)	0.0348 (6)
C4	0.2294 (2)	0.38661 (18)	0.2018 (2)	0.0331 (6)
C4A	0.2587 (2)	0.39087 (17)	0.31112 (19)	0.0284 (6)
C5	0.1640 (2)	0.3974 (2)	0.3862 (2)	0.0361 (6)
C6	0.2067 (2)	0.44836 (18)	0.48871 (19)	0.0292 (6)
C6A	0.3282 (2)	0.41464 (16)	0.53671 (19)	0.0230 (5)
C7	0.3622 (2)	0.41736 (16)	0.64524 (19)	0.0249 (6)
C71	0.27679 (19)	0.44442 (17)	0.72279 (18)	0.0231 (5)
C72	0.2492 (2)	0.37679 (18)	0.79790 (19)	0.0276 (6)
N73	0.17335 (18)	0.39308 (16)	0.87091 (16)	0.0355 (5)
C74	0.1238 (2)	0.4814 (2)	0.8702 (2)	0.0405 (7)
C75	0.1453 (2)	0.5542 (2)	0.7998 (2)	0.0383 (7)
C76	0.2224 (2)	0.53564 (18)	0.7242 (2)	0.0296 (6)
C7A	0.4801 (2)	0.38918 (16)	0.68073 (18)	0.0226 (5)
C8	0.5537 (2)	0.38331 (16)	0.77909 (18)	0.0242 (5)
C81	0.5256 (2)	0.40234 (18)	0.88976 (18)	0.0303 (6)
N9	0.66326 (17)	0.35376 (14)	0.76365 (15)	0.0261 (5)
N10	0.66424 (16)	0.33897 (14)	0.65594 (15)	0.0247 (5)
C101	0.7709 (2)	0.30740 (16)	0.61566 (19)	0.0252 (6)
C102	0.8805 (2)	0.32605 (17)	0.67353 (19)	0.0276 (6)
C103	0.9843 (2)	0.29278 (18)	0.6351 (2)	0.0321 (6)
C104	0.9811 (2)	0.24307 (19)	0.5400 (2)	0.0343 (6)
C105	0.8717 (2)	0.22735 (19)	0.4826 (2)	0.0339 (6)
C106	0.7663 (2)	0.25830 (18)	0.51979 (18)	0.0289 (6)
C10A	0.5543 (2)	0.36121 (16)	0.60378 (18)	0.0216 (5)
N11	0.52538 (17)	0.35726 (14)	0.49931 (15)	0.0241 (5)
C11A	0.4128 (2)	0.38402 (16)	0.46696 (18)	0.0223 (5)
C11B	0.3784 (2)	0.38026 (16)	0.35164 (18)	0.0240 (5)
H1	0.5466	0.3550	0.3085	0.033*
H2	0.4935	0.3450	0.1272	0.037*
H3	0.2928	0.3666	0.0593	0.042*
H4	0.1484	0.3956	0.1738	0.040*
H5A	0.1373	0.3307	0.4023	0.043*
H5B	0.0942	0.4330	0.3513	0.043*
H6A	0.2099	0.5194	0.4755	0.035*
H6B	0.1476	0.4371	0.5404	0.035*
H72	0.2867	0.3147	0.7975	0.033*
H74	0.0702	0.4951	0.9216	0.049*
H75	0.1076	0.6160	0.8032	0.046*
H76	0.2382	0.5842	0.6740	0.036*
H81A	0.4866	0.3449	0.9168	0.045*
H81B	0.4718	0.4586	0.8904	0.045*
H81C	0.5998	0.4160	0.9347	0.045*
H102	0.8840	0.3611	0.7384	0.033*
H103	1.0592	0.3043	0.6748	0.039*
H104	1.0528	0.2202	0.5146	0.041*
H105	0.8687	0.1947	0.4164	0.041*
H106	0.6916	0.2460	0.4801	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0323 (14)	0.0244 (13)	0.0262 (15)	−0.0001 (11)	0.0002 (12)	0.0001 (11)
C2	0.0409 (16)	0.0278 (14)	0.0248 (15)	0.0022 (12)	0.0035 (12)	−0.0004 (11)
C3	0.0462 (17)	0.0349 (15)	0.0219 (14)	0.0005 (13)	−0.0040 (13)	0.0033 (12)
C4	0.0343 (15)	0.0346 (15)	0.0283 (15)	−0.0016 (12)	−0.0071 (12)	0.0019 (12)
C4A	0.0330 (14)	0.0252 (13)	0.0262 (15)	−0.0027 (11)	−0.0020 (12)	0.0036 (11)
C5	0.0315 (14)	0.0460 (16)	0.0294 (15)	0.0003 (13)	−0.0034 (12)	0.0062 (13)
C6	0.0284 (14)	0.0317 (14)	0.0272 (15)	0.0029 (11)	0.0015 (11)	0.0065 (11)
C6A	0.0245 (13)	0.0201 (12)	0.0242 (14)	−0.0011 (10)	0.0016 (11)	0.0017 (10)
C7	0.0283 (13)	0.0219 (12)	0.0242 (14)	0.0018 (10)	0.0013 (11)	0.0020 (10)
C71	0.0212 (12)	0.0241 (13)	0.0232 (14)	−0.0011 (10)	−0.0014 (10)	−0.0015 (10)
C72	0.0279 (13)	0.0287 (14)	0.0260 (14)	0.0002 (11)	0.0009 (11)	−0.0008 (11)
N73	0.0339 (12)	0.0476 (14)	0.0256 (13)	−0.0063 (11)	0.0061 (10)	0.0001 (11)
C74	0.0332 (16)	0.0570 (19)	0.0329 (17)	0.0018 (14)	0.0114 (13)	−0.0106 (14)
C75	0.0321 (15)	0.0396 (16)	0.0432 (18)	0.0078 (13)	0.0041 (13)	−0.0083 (14)
C76	0.0279 (13)	0.0288 (14)	0.0312 (15)	−0.0004 (11)	−0.0012 (11)	0.0006 (11)
C7A	0.0284 (13)	0.0196 (12)	0.0192 (13)	−0.0005 (10)	−0.0005 (10)	0.0007 (10)
C8	0.0286 (13)	0.0214 (12)	0.0221 (13)	−0.0006 (11)	0.0004 (11)	0.0018 (10)
C81	0.0338 (14)	0.0334 (14)	0.0231 (14)	0.0028 (12)	0.0002 (11)	0.0001 (11)
N9	0.0308 (12)	0.0290 (11)	0.0179 (11)	0.0009 (9)	0.0000 (9)	−0.0010 (9)
N10	0.0243 (11)	0.0303 (11)	0.0187 (11)	0.0022 (9)	−0.0016 (9)	0.0003 (9)
C101	0.0260 (13)	0.0253 (13)	0.0241 (14)	−0.0009 (10)	0.0015 (11)	0.0046 (11)
C102	0.0285 (14)	0.0286 (13)	0.0247 (14)	−0.0032 (11)	−0.0028 (11)	0.0024 (11)
C103	0.0246 (14)	0.0394 (15)	0.0312 (16)	−0.0059 (12)	−0.0033 (12)	0.0082 (12)
C104	0.0283 (15)	0.0446 (16)	0.0310 (16)	0.0020 (13)	0.0077 (12)	0.0111 (13)
C105	0.0345 (15)	0.0459 (16)	0.0217 (14)	0.0031 (13)	0.0040 (12)	0.0008 (12)
C106	0.0282 (14)	0.0362 (15)	0.0214 (14)	0.0007 (12)	−0.0023 (11)	−0.0017 (11)
C10A	0.0221 (12)	0.0209 (12)	0.0210 (13)	−0.0020 (10)	−0.0014 (10)	0.0001 (10)
N11	0.0247 (11)	0.0268 (11)	0.0201 (11)	0.0001 (9)	−0.0015 (9)	0.0004 (9)
C11A	0.0249 (13)	0.0190 (12)	0.0221 (13)	−0.0029 (10)	−0.0020 (10)	0.0020 (10)
C11B	0.0291 (13)	0.0194 (12)	0.0224 (13)	−0.0028 (10)	−0.0028 (11)	0.0020 (10)

Geometric parameters (Å, º)

C1—C2	1.379 (3)	C75—C76	1.379 (3)
C1—C11B	1.405 (3)	C75—H75	0.95
C1—H1	0.95	C76—H76	0.95
C2—C3	1.394 (4)	C7A—C10A	1.399 (3)
C2—H2	0.95	C7A—C8	1.429 (3)
C3—C4	1.376 (3)	C8—N9	1.328 (3)
C3—H3	0.95	C8—C81	1.493 (3)
C4—C4A	1.395 (3)	C81—H81A	0.98
C4—H4	0.95	C81—H81B	0.98
C4A—C11B	1.398 (3)	C81—H81C	0.98
C4A—C5	1.499 (3)	N9—N10	1.383 (2)
C5—C6	1.512 (3)	N10—C10A	1.375 (3)
C5—H5A	0.99	N10—C101	1.416 (3)
C5—H5B	0.99	C101—C106	1.387 (3)
C6—C6A	1.510 (3)	C101—C102	1.393 (3)
C6—H6A	0.99	C102—C103	1.385 (3)
C6—H6B	0.99	C102—H102	0.95
C6A—C7	1.393 (3)	C103—C104	1.384 (3)
C6A—C11A	1.424 (3)	C103—H103	0.95
C7—C7A	1.408 (3)	C104—C105	1.381 (3)
C7—C71	1.488 (3)	C104—H104	0.95
C71—C72	1.387 (3)	C105—C106	1.383 (3)
C71—C76	1.392 (3)	C105—H105	0.95
C72—N73	1.339 (3)	C106—H106	0.95
C72—H72	0.95	C10A—N11	1.334 (3)
N73—C74	1.332 (3)	N11—C11A	1.341 (3)
C74—C75	1.377 (4)	C11A—C11B	1.477 (3)
C74—H74	0.95
C2—C1—C11B	121.0 (2)	C75—C76—H76	120.6
C2—C1—H1	119.5	C71—C76—H76	120.6
C11B—C1—H1	119.5	C10A—C7A—C7	117.3 (2)
C1—C2—C3	119.8 (2)	C10A—C7A—C8	105.15 (19)
C1—C2—H2	120.1	C7—C7A—C8	137.5 (2)
C3—C2—H2	120.1	N9—C8—C7A	110.6 (2)
C4—C3—C2	119.5 (2)	N9—C8—C81	118.6 (2)
C4—C3—H3	120.2	C7A—C8—C81	130.8 (2)
C2—C3—H3	120.2	C8—C81—H81A	109.5
C3—C4—C4A	121.6 (2)	C8—C81—H81B	109.5
C3—C4—H4	119.2	H81A—C81—H81B	109.5
C4A—C4—H4	119.2	C8—C81—H81C	109.5
C4—C4A—C11B	119.0 (2)	H81A—C81—H81C	109.5
C4—C4A—C5	121.5 (2)	H81B—C81—H81C	109.5
C11B—C4A—C5	119.3 (2)	C8—N9—N10	106.83 (18)
C4A—C5—C6	113.0 (2)	C10A—N10—N9	110.36 (18)
C4A—C5—H5A	109.0	C10A—N10—C101	130.14 (19)
C6—C5—H5A	109.0	N9—N10—C101	119.49 (18)
C4A—C5—H5B	109.0	C106—C101—C102	120.3 (2)
C6—C5—H5B	109.0	C106—C101—N10	120.4 (2)
H5A—C5—H5B	107.8	C102—C101—N10	119.2 (2)
C6A—C6—C5	113.7 (2)	C103—C102—C101	119.0 (2)
C6A—C6—H6A	108.8	C103—C102—H102	120.5
C5—C6—H6A	108.8	C101—C102—H102	120.5
C6A—C6—H6B	108.8	C104—C103—C102	121.3 (2)
C5—C6—H6B	108.8	C104—C103—H103	119.3
H6A—C6—H6B	107.7	C102—C103—H103	119.3
C7—C6A—C11A	119.3 (2)	C105—C104—C103	118.8 (2)
C7—C6A—C6	122.6 (2)	C105—C104—H104	120.6
C11A—C6A—C6	118.1 (2)	C103—C104—H104	120.6
C6A—C7—C7A	117.7 (2)	C104—C105—C106	121.2 (2)
C6A—C7—C71	122.0 (2)	C104—C105—H105	119.4
C7A—C7—C71	120.2 (2)	C106—C105—H105	119.4
C72—C71—C76	117.6 (2)	C105—C106—C101	119.4 (2)
C72—C71—C7	119.4 (2)	C105—C106—H106	120.3
C76—C71—C7	123.0 (2)	C101—C106—H106	120.3
N73—C72—C71	124.4 (2)	N11—C10A—N10	125.9 (2)
N73—C72—H72	117.8	N11—C10A—C7A	127.0 (2)
C71—C72—H72	117.8	N10—C10A—C7A	107.05 (19)
C74—N73—C72	116.2 (2)	C10A—N11—C11A	114.93 (19)
N73—C74—C75	124.3 (2)	N11—C11A—C6A	123.8 (2)
N73—C74—H74	117.9	N11—C11A—C11B	116.05 (19)
C75—C74—H74	117.9	C6A—C11A—C11B	120.1 (2)
C74—C75—C76	118.7 (2)	C4A—C11B—C1	119.1 (2)
C74—C75—H75	120.6	C4A—C11B—C11A	120.5 (2)
C76—C75—H75	120.6	C1—C11B—C11A	120.3 (2)
C75—C76—C71	118.8 (2)
C11B—C1—C2—C3	0.5 (4)	C10A—N10—C101—C106	−25.7 (4)
C1—C2—C3—C4	−0.6 (4)	N9—N10—C101—C106	156.0 (2)
C2—C3—C4—C4A	−0.5 (4)	C10A—N10—C101—C102	154.5 (2)
C3—C4—C4A—C11B	1.7 (4)	N9—N10—C101—C102	−23.9 (3)
C3—C4—C4A—C5	−172.6 (2)	C106—C101—C102—C103	−1.5 (3)
C4—C4A—C5—C6	−152.2 (2)	N10—C101—C102—C103	178.3 (2)
C11B—C4A—C5—C6	33.5 (3)	C101—C102—C103—C104	1.1 (4)
C4A—C5—C6—C6A	−45.8 (3)	C102—C103—C104—C105	0.4 (4)
C5—C6—C6A—C7	−151.7 (2)	C103—C104—C105—C106	−1.5 (4)
C5—C6—C6A—C11A	31.8 (3)	C104—C105—C106—C101	1.1 (4)
C11A—C6A—C7—C7A	−0.1 (3)	C102—C101—C106—C105	0.5 (4)
C6—C6A—C7—C7A	−176.6 (2)	N10—C101—C106—C105	−179.4 (2)
C11A—C6A—C7—C71	−177.3 (2)	N9—N10—C10A—N11	178.3 (2)
C6—C6A—C7—C71	6.3 (3)	C101—N10—C10A—N11	−0.2 (4)
C6A—C7—C71—C72	117.8 (3)	N9—N10—C10A—C7A	−1.2 (2)
C7A—C7—C71—C72	−59.4 (3)	C101—N10—C10A—C7A	−179.7 (2)
C6A—C7—C71—C76	−62.5 (3)	C7—C7A—C10A—N11	−0.7 (3)
C7A—C7—C71—C76	120.4 (3)	C8—C7A—C10A—N11	−178.6 (2)
C76—C71—C72—N73	0.5 (4)	C7—C7A—C10A—N10	178.8 (2)
C7—C71—C72—N73	−179.7 (2)	C8—C7A—C10A—N10	0.9 (2)
C71—C72—N73—C74	−1.0 (4)	N10—C10A—N11—C11A	−178.9 (2)
C72—N73—C74—C75	0.6 (4)	C7A—C10A—N11—C11A	0.5 (3)
N73—C74—C75—C76	0.3 (4)	C10A—N11—C11A—C6A	0.0 (3)
C74—C75—C76—C71	−0.7 (4)	C10A—N11—C11A—C11B	−179.96 (19)
C72—C71—C76—C75	0.4 (3)	C7—C6A—C11A—N11	−0.2 (3)
C7—C71—C76—C75	−179.4 (2)	C6—C6A—C11A—N11	176.5 (2)
C6A—C7—C7A—C10A	0.4 (3)	C7—C6A—C11A—C11B	179.8 (2)
C71—C7—C7A—C10A	177.7 (2)	C6—C6A—C11A—C11B	−3.6 (3)
C6A—C7—C7A—C8	177.4 (2)	C4—C4A—C11B—C1	−1.7 (3)
C71—C7—C7A—C8	−5.3 (4)	C5—C4A—C11B—C1	172.7 (2)
C10A—C7A—C8—N9	−0.3 (3)	C4—C4A—C11B—C11A	−179.8 (2)
C7—C7A—C8—N9	−177.6 (3)	C5—C4A—C11B—C11A	−5.3 (3)
C10A—C7A—C8—C81	−178.8 (2)	C2—C1—C11B—C4A	0.6 (3)
C7—C7A—C8—C81	3.9 (5)	C2—C1—C11B—C11A	178.7 (2)
C7A—C8—N9—N10	−0.4 (2)	N11—C11A—C11B—C4A	169.4 (2)
C81—C8—N9—N10	178.32 (19)	C6A—C11A—C11B—C4A	−10.6 (3)
C8—N9—N10—C10A	1.0 (2)	N11—C11A—C11B—C1	−8.7 (3)
C8—N9—N10—C101	179.64 (19)	C6A—C11A—C11B—C1	171.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C72—H72···Cg1^i	0.95	2.79	3.706 (3)	163
C75—H75···Cg2^ii	0.95	2.66	3.431 (3)	139

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2.

(VIII) 11-(4-methylphenyl)-10-methyl-8-phenyl-6,8-dihydro- 5H-benzo[f]pyrazolo[3,4-b]quinoline

Crystal data

C28H23N3	Z = 4
Mr = 401.49	F(000) = 848
Triclinic, P1	Dx = 1.265 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1334 (3) Å	Cell parameters from 9647 reflections
b = 11.4672 (2) Å	θ = 3.1–27.5°
c = 17.6270 (4) Å	µ = 0.08 mm^−1
α = 97.858 (2)°	T = 118 K
β = 106.135 (3)°	Block, colourless
γ = 97.496 (2)°	0.20 × 0.18 × 0.12 mm
V = 2107.66 (9) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	9647 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	7878 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ & ω scans	h = −14→14
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.982, Tmax = 0.991	l = −22→22
40500 measured 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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 0.8878P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
9647 reflections	Δρmax = 0.27 e Å^−3
564 parameters	Δρmin = −0.25 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: 0.0084 (11)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.76702 (13)	0.13359 (12)	0.70638 (8)	0.0231 (3)
C12	0.84744 (13)	0.06640 (13)	0.74874 (8)	0.0270 (3)
C13	0.79830 (14)	−0.04070 (13)	0.76593 (8)	0.0291 (3)
C14	0.66844 (14)	−0.08129 (12)	0.73877 (8)	0.0274 (3)
C14A	0.58640 (13)	−0.01522 (12)	0.69584 (8)	0.0233 (3)
C15	0.44612 (13)	−0.06230 (12)	0.66176 (8)	0.0260 (3)
C16	0.40133 (13)	−0.03677 (12)	0.57661 (8)	0.0250 (3)
C16A	0.42946 (12)	0.09592 (11)	0.57860 (7)	0.0206 (3)
N17	0.33956 (10)	0.14059 (10)	0.53005 (6)	0.0217 (2)
C17A	0.36189 (12)	0.25987 (12)	0.53819 (8)	0.0215 (3)
N18	0.27858 (10)	0.32785 (10)	0.50155 (7)	0.0232 (2)
C181	0.15148 (12)	0.29245 (12)	0.45074 (8)	0.0233 (3)
C182	0.06670 (14)	0.37166 (13)	0.44997 (8)	0.0288 (3)
C183	−0.05767 (14)	0.33700 (14)	0.40046 (9)	0.0324 (3)
C184	−0.09774 (14)	0.22439 (14)	0.35293 (8)	0.0312 (3)
C185	−0.01271 (14)	0.14644 (14)	0.35424 (8)	0.0313 (3)
C186	0.11247 (14)	0.17981 (13)	0.40228 (8)	0.0277 (3)
N19	0.32713 (11)	0.44784 (10)	0.53033 (7)	0.0252 (3)
C110	0.44023 (13)	0.45582 (12)	0.58249 (8)	0.0232 (3)
C111	0.51441 (14)	0.57777 (12)	0.62257 (9)	0.0281 (3)
C11A	0.46874 (12)	0.33862 (12)	0.59048 (8)	0.0214 (3)
C120	0.56542 (12)	0.28977 (12)	0.63979 (7)	0.0202 (3)
C121	0.67737 (12)	0.37387 (11)	0.69659 (8)	0.0211 (3)
C122	0.70603 (13)	0.37927 (12)	0.77959 (8)	0.0234 (3)
C123	0.80874 (13)	0.45979 (13)	0.83192 (8)	0.0272 (3)
C124	0.88571 (13)	0.53841 (13)	0.80359 (9)	0.0283 (3)
C127	0.99923 (15)	0.62415 (15)	0.86080 (10)	0.0416 (4)
C125	0.85528 (13)	0.53406 (12)	0.72125 (9)	0.0283 (3)
C126	0.75319 (13)	0.45290 (12)	0.66827 (8)	0.0249 (3)
C12A	0.54504 (12)	0.16477 (11)	0.63347 (7)	0.0200 (3)
C12B	0.63528 (12)	0.09562 (11)	0.68004 (7)	0.0210 (3)
C21	0.26100 (13)	0.10371 (12)	0.85434 (8)	0.0235 (3)
C22	0.21280 (14)	−0.01670 (12)	0.84542 (8)	0.0268 (3)
C23	0.29433 (14)	−0.09863 (12)	0.85298 (8)	0.0291 (3)
C24	0.42420 (14)	−0.06002 (12)	0.87372 (8)	0.0284 (3)
C24A	0.47414 (13)	0.06119 (12)	0.88507 (8)	0.0238 (3)
C25	0.61529 (14)	0.10783 (12)	0.91573 (9)	0.0291 (3)
C26	0.63935 (13)	0.22366 (12)	0.97612 (8)	0.0272 (3)
C26A	0.56894 (12)	0.31343 (11)	0.93711 (7)	0.0204 (3)
N27	0.62967 (10)	0.42643 (9)	0.95639 (6)	0.0203 (2)
C27A	0.56717 (12)	0.50140 (11)	0.91516 (7)	0.0191 (3)
N28	0.61281 (10)	0.61981 (9)	0.91951 (6)	0.0216 (2)
C281	0.73369 (13)	0.68915 (11)	0.96228 (8)	0.0225 (3)
C282	0.77068 (15)	0.79603 (13)	0.93996 (9)	0.0345 (4)
C283	0.89001 (16)	0.86292 (14)	0.97970 (10)	0.0428 (4)
C284	0.97328 (15)	0.82448 (14)	1.04163 (9)	0.0346 (4)
C285	0.93559 (14)	0.71839 (12)	1.06406 (8)	0.0274 (3)
C286	0.81590 (13)	0.65044 (12)	1.02510 (8)	0.0244 (3)
N29	0.53025 (11)	0.66579 (10)	0.86193 (7)	0.0239 (2)
C210	0.43371 (12)	0.57910 (11)	0.82319 (8)	0.0214 (3)
C211	0.33001 (13)	0.60331 (12)	0.75570 (8)	0.0265 (3)
C21A	0.45005 (12)	0.47110 (11)	0.85453 (7)	0.0190 (3)
C220	0.38661 (12)	0.35155 (11)	0.83545 (7)	0.0188 (3)
C221	0.26855 (12)	0.31116 (11)	0.76664 (7)	0.0198 (3)
C222	0.26628 (13)	0.22212 (12)	0.70368 (8)	0.0237 (3)
C223	0.15693 (13)	0.18094 (13)	0.63957 (8)	0.0271 (3)
C224	0.04690 (13)	0.22813 (13)	0.63584 (8)	0.0271 (3)
C227	−0.07194 (14)	0.18075 (16)	0.56634 (9)	0.0376 (4)
C225	0.05008 (13)	0.31820 (13)	0.69796 (8)	0.0262 (3)
C226	0.15915 (12)	0.35912 (12)	0.76279 (8)	0.0228 (3)
C22A	0.44649 (12)	0.27213 (11)	0.88046 (7)	0.0199 (3)
C22B	0.39140 (13)	0.14378 (11)	0.87194 (7)	0.0214 (3)
H11	0.8020	0.2069	0.6950	0.028*
H12	0.9366	0.0939	0.7661	0.032*
H13	0.8532	−0.0859	0.7961	0.035*
H14	0.6348	−0.1555	0.7496	0.033*
H15A	0.4000	−0.0227	0.6955	0.031*
H15B	0.4289	−0.1495	0.6608	0.031*
H16A	0.4455	−0.0788	0.5426	0.030*
H16B	0.3089	−0.0665	0.5532	0.030*
H182	0.0937	0.4487	0.4830	0.035*
H183	−0.1157	0.3910	0.3992	0.039*
H184	−0.1832	0.2008	0.3196	0.037*
H185	−0.0404	0.0690	0.3218	0.038*
H186	0.1709	0.1264	0.4021	0.033*
H11A	0.4600	0.6377	0.6107	0.042*
H11B	0.5875	0.5943	0.6025	0.042*
H11C	0.5443	0.5812	0.6808	0.042*
H122	0.6546	0.3272	0.8002	0.028*
H123	0.8273	0.4617	0.8881	0.033*
H12A	1.0636	0.5791	0.8859	0.062*	0.50
H12B	0.9728	0.6704	0.9024	0.062*	0.50
H12C	1.0350	0.6787	0.8312	0.062*	0.50
H12D	0.9840	0.7064	0.8605	0.062*	0.50
H12E	1.0748	0.6150	0.8439	0.062*	0.50
H12F	1.0127	0.6068	0.9152	0.062*	0.50
H125	0.9053	0.5877	0.7007	0.034*
H126	0.7348	0.4512	0.6121	0.030*
H21	0.2047	0.1597	0.8484	0.028*
H22	0.1241	−0.0429	0.8342	0.032*
H23	0.2611	−0.1817	0.8439	0.035*
H24	0.4798	−0.1166	0.8803	0.034*
H25A	0.6478	0.1231	0.8705	0.035*
H25B	0.6600	0.0479	0.9419	0.035*
H26A	0.6107	0.2071	1.0226	0.033*
H26B	0.7315	0.2564	0.9960	0.033*
H282	0.7144	0.8233	0.8976	0.041*
H283	0.9153	0.9362	0.9643	0.051*
H284	1.0553	0.8706	1.0683	0.041*
H285	0.9920	0.6916	1.1066	0.033*
H286	0.7903	0.5779	1.0412	0.029*
H21A	0.3554	0.6818	0.7432	0.040*
H21B	0.2522	0.6026	0.7715	0.040*
H21C	0.3145	0.5414	0.7082	0.040*
H222	0.3406	0.1892	0.7047	0.028*
H223	0.1571	0.1196	0.5975	0.033*
H27A	−0.1158	0.1066	0.5754	0.056*
H27B	−0.0491	0.1647	0.5166	0.056*
H27C	−0.1281	0.2402	0.5619	0.056*
H225	−0.0236	0.3525	0.6961	0.031*
H226	0.1588	0.4204	0.8048	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0225 (7)	0.0249 (7)	0.0211 (6)	0.0031 (5)	0.0065 (5)	0.0022 (5)
C12	0.0205 (7)	0.0331 (7)	0.0245 (7)	0.0070 (6)	0.0029 (5)	0.0014 (6)
C13	0.0292 (8)	0.0315 (7)	0.0245 (7)	0.0113 (6)	0.0019 (6)	0.0050 (6)
C14	0.0315 (8)	0.0237 (7)	0.0250 (7)	0.0049 (6)	0.0057 (6)	0.0043 (5)
C14A	0.0235 (7)	0.0245 (7)	0.0200 (6)	0.0038 (5)	0.0049 (5)	0.0015 (5)
C15	0.0251 (7)	0.0219 (7)	0.0295 (7)	0.0022 (5)	0.0066 (6)	0.0049 (5)
C16	0.0220 (7)	0.0234 (7)	0.0252 (7)	0.0022 (5)	0.0024 (5)	0.0008 (5)
C16A	0.0190 (6)	0.0242 (6)	0.0180 (6)	0.0039 (5)	0.0058 (5)	0.0011 (5)
N17	0.0211 (6)	0.0244 (6)	0.0183 (5)	0.0041 (4)	0.0052 (4)	0.0016 (4)
C17A	0.0210 (6)	0.0259 (7)	0.0179 (6)	0.0051 (5)	0.0061 (5)	0.0041 (5)
N18	0.0214 (6)	0.0237 (6)	0.0221 (6)	0.0044 (4)	0.0025 (5)	0.0043 (4)
C181	0.0207 (7)	0.0303 (7)	0.0179 (6)	0.0045 (5)	0.0034 (5)	0.0062 (5)
C182	0.0277 (7)	0.0317 (8)	0.0241 (7)	0.0074 (6)	0.0036 (6)	0.0020 (6)
C183	0.0263 (8)	0.0414 (9)	0.0277 (7)	0.0133 (6)	0.0025 (6)	0.0056 (6)
C184	0.0234 (7)	0.0424 (9)	0.0228 (7)	0.0049 (6)	−0.0005 (6)	0.0057 (6)
C185	0.0316 (8)	0.0341 (8)	0.0212 (7)	0.0044 (6)	−0.0005 (6)	0.0007 (6)
C186	0.0268 (7)	0.0322 (7)	0.0221 (7)	0.0091 (6)	0.0030 (6)	0.0034 (6)
N19	0.0247 (6)	0.0244 (6)	0.0253 (6)	0.0044 (5)	0.0057 (5)	0.0044 (5)
C110	0.0229 (7)	0.0258 (7)	0.0212 (6)	0.0042 (5)	0.0067 (5)	0.0051 (5)
C111	0.0270 (7)	0.0247 (7)	0.0306 (7)	0.0034 (6)	0.0068 (6)	0.0036 (6)
C11A	0.0204 (6)	0.0243 (6)	0.0191 (6)	0.0027 (5)	0.0060 (5)	0.0031 (5)
C120	0.0186 (6)	0.0253 (6)	0.0173 (6)	0.0030 (5)	0.0074 (5)	0.0028 (5)
C121	0.0189 (6)	0.0213 (6)	0.0222 (6)	0.0043 (5)	0.0048 (5)	0.0028 (5)
C122	0.0221 (7)	0.0245 (7)	0.0230 (7)	0.0033 (5)	0.0068 (5)	0.0026 (5)
C123	0.0247 (7)	0.0323 (7)	0.0218 (7)	0.0053 (6)	0.0055 (6)	−0.0013 (6)
C124	0.0195 (7)	0.0282 (7)	0.0324 (8)	0.0008 (5)	0.0062 (6)	−0.0040 (6)
C127	0.0286 (8)	0.0429 (9)	0.0419 (9)	−0.0074 (7)	0.0072 (7)	−0.0107 (7)
C125	0.0234 (7)	0.0259 (7)	0.0354 (8)	0.0007 (6)	0.0104 (6)	0.0052 (6)
C126	0.0233 (7)	0.0266 (7)	0.0247 (7)	0.0044 (5)	0.0066 (5)	0.0064 (5)
C12A	0.0184 (6)	0.0243 (6)	0.0178 (6)	0.0036 (5)	0.0067 (5)	0.0032 (5)
C12B	0.0215 (7)	0.0238 (6)	0.0167 (6)	0.0046 (5)	0.0049 (5)	0.0010 (5)
C21	0.0256 (7)	0.0225 (6)	0.0205 (6)	0.0027 (5)	0.0048 (5)	0.0035 (5)
C22	0.0279 (7)	0.0257 (7)	0.0215 (7)	−0.0033 (6)	0.0028 (6)	0.0042 (5)
C23	0.0400 (8)	0.0184 (6)	0.0222 (7)	−0.0029 (6)	0.0017 (6)	0.0052 (5)
C24	0.0376 (8)	0.0201 (7)	0.0248 (7)	0.0060 (6)	0.0038 (6)	0.0060 (5)
C24A	0.0290 (7)	0.0209 (6)	0.0202 (6)	0.0046 (5)	0.0042 (5)	0.0059 (5)
C25	0.0278 (8)	0.0219 (7)	0.0358 (8)	0.0079 (6)	0.0030 (6)	0.0097 (6)
C26	0.0250 (7)	0.0243 (7)	0.0273 (7)	0.0023 (5)	−0.0014 (6)	0.0088 (6)
C26A	0.0217 (7)	0.0210 (6)	0.0178 (6)	0.0032 (5)	0.0046 (5)	0.0048 (5)
N27	0.0210 (6)	0.0203 (5)	0.0186 (5)	0.0033 (4)	0.0039 (4)	0.0044 (4)
C27A	0.0209 (6)	0.0183 (6)	0.0176 (6)	0.0034 (5)	0.0055 (5)	0.0020 (5)
N28	0.0217 (6)	0.0170 (5)	0.0221 (5)	0.0031 (4)	0.0007 (4)	0.0029 (4)
C281	0.0229 (7)	0.0190 (6)	0.0211 (6)	0.0014 (5)	0.0028 (5)	−0.0009 (5)
C282	0.0335 (8)	0.0261 (7)	0.0321 (8)	−0.0038 (6)	−0.0064 (6)	0.0087 (6)
C283	0.0415 (9)	0.0292 (8)	0.0423 (9)	−0.0125 (7)	−0.0066 (7)	0.0129 (7)
C284	0.0300 (8)	0.0320 (8)	0.0298 (8)	−0.0078 (6)	−0.0022 (6)	0.0020 (6)
C285	0.0268 (7)	0.0269 (7)	0.0229 (7)	0.0033 (6)	0.0010 (6)	0.0012 (5)
C286	0.0271 (7)	0.0208 (6)	0.0219 (6)	0.0020 (5)	0.0039 (5)	0.0019 (5)
N29	0.0227 (6)	0.0200 (5)	0.0249 (6)	0.0044 (4)	−0.0001 (5)	0.0051 (4)
C210	0.0222 (7)	0.0192 (6)	0.0219 (6)	0.0052 (5)	0.0050 (5)	0.0029 (5)
C211	0.0243 (7)	0.0225 (7)	0.0287 (7)	0.0047 (5)	0.0006 (6)	0.0069 (5)
C21A	0.0191 (6)	0.0199 (6)	0.0179 (6)	0.0046 (5)	0.0052 (5)	0.0024 (5)
C220	0.0186 (6)	0.0204 (6)	0.0171 (6)	0.0033 (5)	0.0060 (5)	0.0014 (5)
C221	0.0186 (6)	0.0207 (6)	0.0194 (6)	0.0019 (5)	0.0042 (5)	0.0059 (5)
C222	0.0213 (7)	0.0260 (7)	0.0233 (7)	0.0033 (5)	0.0072 (5)	0.0029 (5)
C223	0.0257 (7)	0.0328 (7)	0.0198 (6)	−0.0011 (6)	0.0073 (6)	−0.0006 (5)
C224	0.0201 (7)	0.0377 (8)	0.0206 (7)	−0.0024 (6)	0.0038 (5)	0.0082 (6)
C227	0.0232 (8)	0.0588 (10)	0.0233 (7)	−0.0041 (7)	0.0008 (6)	0.0063 (7)
C225	0.0174 (6)	0.0309 (7)	0.0303 (7)	0.0040 (5)	0.0053 (6)	0.0095 (6)
C226	0.0215 (7)	0.0213 (6)	0.0246 (7)	0.0037 (5)	0.0055 (5)	0.0041 (5)
C22A	0.0209 (6)	0.0197 (6)	0.0190 (6)	0.0034 (5)	0.0060 (5)	0.0033 (5)
C22B	0.0249 (7)	0.0198 (6)	0.0173 (6)	0.0014 (5)	0.0036 (5)	0.0035 (5)

Geometric parameters (Å, º)

C11—C12	1.3851 (19)	C12A—C12B	1.4965 (18)
C11—C12B	1.3986 (18)	C21—C22	1.3855 (18)
C11—H11	0.95	C21—C22B	1.3971 (19)
C12—C13	1.385 (2)	C21—H21	0.95
C12—H12	0.95	C22—C23	1.383 (2)
C13—C14	1.384 (2)	C22—H22	0.95
C13—H13	0.95	C23—C24	1.384 (2)
C14—C14A	1.3907 (19)	C23—H23	0.95
C14—H14	0.95	C24—C24A	1.3934 (18)
C14A—C12B	1.4106 (18)	C24—H24	0.95
C14A—C15	1.5038 (19)	C24A—C22B	1.4029 (19)
C15—C16	1.5263 (19)	C24A—C25	1.5090 (19)
C15—H15A	0.99	C25—C26	1.527 (2)
C15—H15B	0.99	C25—H25A	0.99
C16—C16A	1.5065 (18)	C25—H25B	0.99
C16—H16A	0.99	C26—C26A	1.5004 (18)
C16—H16B	0.99	C26—H26A	0.99
C16A—N17	1.3320 (17)	C26—H26B	0.99
C16A—C12A	1.4314 (17)	C26A—N27	1.3323 (16)
N17—C17A	1.3384 (17)	C26A—C22A	1.4232 (18)
C17A—N18	1.3705 (17)	N27—C27A	1.3407 (16)
C17A—C11A	1.4011 (18)	C27A—N28	1.3703 (16)
N18—N19	1.3804 (15)	C27A—C21A	1.4033 (17)
N18—C181	1.4197 (17)	N28—N29	1.3811 (15)
C181—C186	1.3901 (19)	N28—C281	1.4159 (16)
C181—C182	1.3914 (19)	C281—C282	1.3845 (19)
C182—C183	1.388 (2)	C281—C286	1.3922 (18)
C182—H182	0.95	C282—C283	1.383 (2)
C183—C184	1.384 (2)	C282—H282	0.95
C183—H183	0.95	C283—C284	1.386 (2)
C184—C185	1.382 (2)	C283—H283	0.95
C184—H184	0.95	C284—C285	1.379 (2)
C185—C186	1.386 (2)	C284—H284	0.95
C185—H185	0.95	C285—C286	1.3887 (19)
C186—H186	0.95	C285—H285	0.95
N19—C110	1.3202 (17)	C286—H286	0.95
C110—C11A	1.4370 (19)	N29—C210	1.3181 (17)
C110—C111	1.4969 (18)	C210—C21A	1.4359 (18)
C111—H11A	0.98	C210—C211	1.4953 (18)
C111—H11B	0.98	C211—H21A	0.98
C111—H11C	0.98	C211—H21B	0.98
C11A—C120	1.4137 (18)	C211—H21C	0.98
C120—C12A	1.4056 (18)	C21A—C220	1.4073 (17)
C120—C121	1.4882 (18)	C220—C22A	1.4019 (18)
C121—C126	1.3934 (18)	C220—C221	1.4883 (17)
C121—C122	1.3988 (18)	C221—C226	1.3892 (18)
C122—C123	1.3844 (19)	C221—C222	1.3937 (18)
C122—H122	0.95	C222—C223	1.3862 (19)
C123—C124	1.398 (2)	C222—H222	0.95
C123—H123	0.95	C223—C224	1.391 (2)
C124—C125	1.388 (2)	C223—H223	0.95
C124—C127	1.509 (2)	C224—C225	1.388 (2)
C127—H12A	0.98	C224—C227	1.5087 (19)
C127—H12B	0.98	C227—H27A	0.98
C127—H12C	0.98	C227—H27B	0.98
C127—H12D	0.98	C227—H27C	0.98
C127—H12E	0.98	C225—C226	1.3907 (18)
C127—H12F	0.98	C225—H225	0.95
C125—C126	1.3880 (19)	C226—H226	0.95
C125—H125	0.95	C22A—C22B	1.4892 (17)
C126—H126	0.95
C12—C11—C12B	121.27 (13)	C121—C126—H126	119.7
C12—C11—H11	119.4	C120—C12A—C16A	118.66 (11)
C12B—C11—H11	119.4	C120—C12A—C12B	125.22 (11)
C13—C12—C11	120.26 (13)	C16A—C12A—C12B	116.12 (11)
C13—C12—H12	119.9	C11—C12B—C14A	118.04 (12)
C11—C12—H12	119.9	C11—C12B—C12A	123.04 (12)
C14—C13—C12	119.39 (13)	C14A—C12B—C12A	118.87 (11)
C14—C13—H13	120.3	C22—C21—C22B	120.78 (13)
C12—C13—H13	120.3	C22—C21—H21	119.6
C13—C14—C14A	121.08 (13)	C22B—C21—H21	119.6
C13—C14—H14	119.5	C23—C22—C21	119.76 (13)
C14A—C14—H14	119.5	C23—C22—H22	120.1
C14—C14A—C12B	119.91 (12)	C21—C22—H22	120.1
C14—C14A—C15	121.33 (12)	C22—C23—C24	120.20 (13)
C12B—C14A—C15	118.68 (12)	C22—C23—H23	119.9
C14A—C15—C16	108.42 (11)	C24—C23—H23	119.9
C14A—C15—H15A	110.0	C23—C24—C24A	120.53 (13)
C16—C15—H15A	110.0	C23—C24—H24	119.7
C14A—C15—H15B	110.0	C24A—C24—H24	119.7
C16—C15—H15B	110.0	C24—C24A—C22B	119.46 (13)
H15A—C15—H15B	108.4	C24—C24A—C25	121.97 (12)
C16A—C16—C15	109.56 (11)	C22B—C24A—C25	118.49 (11)
C16A—C16—H16A	109.8	C24A—C25—C26	108.59 (12)
C15—C16—H16A	109.8	C24A—C25—H25A	110.0
C16A—C16—H16B	109.8	C26—C25—H25A	110.0
C15—C16—H16B	109.8	C24A—C25—H25B	110.0
H16A—C16—H16B	108.2	C26—C25—H25B	110.0
N17—C16A—C12A	125.03 (12)	H25A—C25—H25B	108.4
N17—C16A—C16	115.80 (11)	C26A—C26—C25	110.00 (11)
C12A—C16A—C16	119.11 (11)	C26A—C26—H26A	109.7
C16A—N17—C17A	114.53 (11)	C25—C26—H26A	109.7
N17—C17A—N18	125.70 (12)	C26A—C26—H26B	109.7
N17—C17A—C11A	126.69 (12)	C25—C26—H26B	109.7
N18—C17A—C11A	107.39 (11)	H26A—C26—H26B	108.2
C17A—N18—N19	110.11 (10)	N27—C26A—C22A	124.99 (11)
C17A—N18—C181	129.74 (11)	N27—C26A—C26	116.41 (11)
N19—N18—C181	119.48 (11)	C22A—C26A—C26	118.54 (11)
C186—C181—C182	120.48 (13)	C26A—N27—C27A	114.10 (11)
C186—C181—N18	120.21 (12)	N27—C27A—N28	125.53 (11)
C182—C181—N18	119.31 (12)	N27—C27A—C21A	126.59 (11)
C183—C182—C181	119.35 (13)	N28—C27A—C21A	107.60 (11)
C183—C182—H182	120.3	C27A—N28—N29	109.92 (10)
C181—C182—H182	120.3	C27A—N28—C281	129.99 (11)
C184—C183—C182	120.52 (14)	N29—N28—C281	119.14 (10)
C184—C183—H183	119.7	C282—C281—C286	119.92 (12)
C182—C183—H183	119.7	C282—C281—N28	119.04 (12)
C185—C184—C183	119.62 (13)	C286—C281—N28	121.03 (12)
C185—C184—H184	120.2	C283—C282—C281	119.63 (14)
C183—C184—H184	120.2	C283—C282—H282	120.2
C184—C185—C186	120.85 (14)	C281—C282—H282	120.2
C184—C185—H185	119.6	C282—C283—C284	120.94 (14)
C186—C185—H185	119.6	C282—C283—H283	119.5
C185—C186—C181	119.16 (13)	C284—C283—H283	119.5
C185—C186—H186	120.4	C285—C284—C283	119.20 (14)
C181—C186—H186	120.4	C285—C284—H284	120.4
C110—N19—N18	107.42 (11)	C283—C284—H284	120.4
N19—C110—C11A	110.36 (12)	C284—C285—C286	120.62 (13)
N19—C110—C111	118.24 (12)	C284—C285—H285	119.7
C11A—C110—C111	131.40 (12)	C286—C285—H285	119.7
C110—C111—H11A	109.5	C285—C286—C281	119.68 (13)
C110—C111—H11B	109.5	C285—C286—H286	120.2
H11A—C111—H11B	109.5	C281—C286—H286	120.2
C110—C111—H11C	109.5	C210—N29—N28	107.42 (10)
H11A—C111—H11C	109.5	N29—C210—C21A	110.65 (11)
H11B—C111—H11C	109.5	N29—C210—C211	119.02 (11)
C17A—C11A—C120	118.21 (12)	C21A—C210—C211	130.31 (12)
C17A—C11A—C110	104.70 (11)	C210—C211—H21A	109.5
C120—C11A—C110	136.79 (12)	C210—C211—H21B	109.5
C12A—C120—C11A	116.82 (11)	H21A—C211—H21B	109.5
C12A—C120—C121	125.09 (12)	C210—C211—H21C	109.5
C11A—C120—C121	118.03 (11)	H21A—C211—H21C	109.5
C126—C121—C122	118.35 (12)	H21B—C211—H21C	109.5
C126—C121—C120	120.50 (12)	C27A—C21A—C220	118.54 (11)
C122—C121—C120	121.09 (12)	C27A—C21A—C210	104.38 (11)
C123—C122—C121	120.56 (13)	C220—C21A—C210	136.84 (12)
C123—C122—H122	119.7	C22A—C220—C21A	116.20 (11)
C121—C122—H122	119.7	C22A—C220—C221	122.43 (11)
C122—C123—C124	121.18 (13)	C21A—C220—C221	121.17 (11)
C122—C123—H123	119.4	C226—C221—C222	118.31 (12)
C124—C123—H123	119.4	C226—C221—C220	122.17 (12)
C125—C124—C123	117.92 (13)	C222—C221—C220	119.53 (12)
C125—C124—C127	121.12 (14)	C223—C222—C221	120.84 (13)
C123—C124—C127	120.95 (14)	C223—C222—H222	119.6
C124—C127—H12A	109.5	C221—C222—H222	119.6
C124—C127—H12B	109.5	C222—C223—C224	120.99 (13)
H12A—C127—H12B	109.5	C222—C223—H223	119.5
C124—C127—H12C	109.5	C224—C223—H223	119.5
H12A—C127—H12C	109.5	C225—C224—C223	118.04 (12)
H12B—C127—H12C	109.5	C225—C224—C227	121.68 (14)
C124—C127—H12D	109.5	C223—C224—C227	120.28 (14)
H12A—C127—H12D	141.1	C224—C227—H27A	109.5
H12B—C127—H12D	56.3	C224—C227—H27B	109.5
H12C—C127—H12D	56.3	H27A—C227—H27B	109.5
C124—C127—H12E	109.5	C224—C227—H27C	109.5
H12A—C127—H12E	56.3	H27A—C227—H27C	109.5
H12B—C127—H12E	141.1	H27B—C227—H27C	109.5
H12C—C127—H12E	56.3	C224—C225—C226	121.23 (13)
H12D—C127—H12E	109.5	C224—C225—H225	119.4
C124—C127—H12F	109.5	C226—C225—H225	119.4
H12A—C127—H12F	56.3	C221—C226—C225	120.58 (13)
H12B—C127—H12F	56.3	C221—C226—H226	119.7
H12C—C127—H12F	141.1	C225—C226—H226	119.7
H12D—C127—H12F	109.5	C220—C22A—C26A	119.35 (11)
H12E—C127—H12F	109.5	C220—C22A—C22B	124.13 (11)
C124—C125—C126	121.31 (13)	C26A—C22A—C22B	116.50 (11)
C124—C125—H125	119.3	C21—C22B—C24A	119.02 (12)
C126—C125—H125	119.3	C21—C22B—C22A	122.33 (12)
C125—C126—C121	120.65 (13)	C24A—C22B—C22A	118.60 (12)
C125—C126—H126	119.7
C12B—C11—C12—C13	0.0 (2)	C22B—C21—C22—C23	−0.8 (2)
C11—C12—C13—C14	1.5 (2)	C21—C22—C23—C24	3.6 (2)
C12—C13—C14—C14A	−1.2 (2)	C22—C23—C24—C24A	−1.8 (2)
C13—C14—C14A—C12B	−0.6 (2)	C23—C24—C24A—C22B	−2.7 (2)
C13—C14—C14A—C15	176.16 (13)	C23—C24—C24A—C25	173.74 (13)
C14—C14A—C15—C16	−136.53 (13)	C24—C24A—C25—C26	−138.76 (13)
C12B—C14A—C15—C16	40.27 (16)	C22B—C24A—C25—C26	37.75 (17)
C14A—C15—C16—C16A	−58.96 (14)	C24A—C25—C26—C26A	−58.16 (15)
C15—C16—C16A—N17	−139.54 (12)	C25—C26—C26A—N27	−140.26 (12)
C15—C16—C16A—C12A	37.77 (16)	C25—C26—C26A—C22A	37.05 (17)
C12A—C16A—N17—C17A	−2.79 (18)	C22A—C26A—N27—C27A	−2.27 (19)
C16—C16A—N17—C17A	174.34 (11)	C26—C26A—N27—C27A	174.85 (12)
C16A—N17—C17A—N18	−172.80 (12)	C26A—N27—C27A—N28	−175.05 (12)
C16A—N17—C17A—C11A	1.12 (19)	C26A—N27—C27A—C21A	−1.89 (19)
N17—C17A—N18—N19	173.26 (12)	N27—C27A—N28—N29	172.57 (12)
C11A—C17A—N18—N19	−1.63 (14)	C21A—C27A—N28—N29	−1.68 (14)
N17—C17A—N18—C181	2.9 (2)	N27—C27A—N28—C281	4.1 (2)
C11A—C17A—N18—C181	−172.01 (12)	C21A—C27A—N28—C281	−170.15 (12)
C17A—N18—C181—C186	−29.8 (2)	C27A—N28—C281—C282	161.39 (14)
N19—N18—C181—C186	160.56 (12)	N29—N28—C281—C282	−6.19 (19)
C17A—N18—C181—C182	150.26 (14)	C27A—N28—C281—C286	−17.5 (2)
N19—N18—C181—C182	−19.36 (18)	N29—N28—C281—C286	174.89 (12)
C186—C181—C182—C183	0.2 (2)	C286—C281—C282—C283	0.8 (2)
N18—C181—C182—C183	−179.84 (13)	N28—C281—C282—C283	−178.09 (15)
C181—C182—C183—C184	0.7 (2)	C281—C282—C283—C284	0.0 (3)
C182—C183—C184—C185	−0.7 (2)	C282—C283—C284—C285	−0.5 (3)
C183—C184—C185—C186	−0.3 (2)	C283—C284—C285—C286	0.2 (2)
C184—C185—C186—C181	1.3 (2)	C284—C285—C286—C281	0.7 (2)
C182—C181—C186—C185	−1.2 (2)	C282—C281—C286—C285	−1.2 (2)
N18—C181—C186—C185	178.85 (12)	N28—C281—C286—C285	177.74 (12)
C17A—N18—N19—C110	1.60 (15)	C27A—N28—N29—C210	1.12 (15)
C181—N18—N19—C110	173.12 (11)	C281—N28—N29—C210	171.03 (11)
N18—N19—C110—C11A	−0.93 (15)	N28—N29—C210—C21A	−0.12 (15)
N18—N19—C110—C111	179.63 (11)	N28—N29—C210—C211	−178.76 (12)
N17—C17A—C11A—C120	0.9 (2)	N27—C27A—C21A—C220	2.6 (2)
N18—C17A—C11A—C120	175.73 (11)	N28—C27A—C21A—C220	176.74 (11)
N17—C17A—C11A—C110	−173.81 (13)	N27—C27A—C21A—C210	−172.65 (12)
N18—C17A—C11A—C110	1.01 (14)	N28—C27A—C21A—C210	1.52 (14)
N19—C110—C11A—C17A	−0.04 (15)	N29—C210—C21A—C27A	−0.88 (15)
C111—C110—C11A—C17A	179.29 (14)	C211—C210—C21A—C27A	177.57 (14)
N19—C110—C11A—C120	−173.24 (15)	N29—C210—C21A—C220	−174.74 (15)
C111—C110—C11A—C120	6.1 (3)	C211—C210—C21A—C220	3.7 (3)
C17A—C11A—C120—C12A	−1.30 (18)	C27A—C21A—C220—C22A	0.89 (18)
C110—C11A—C120—C12A	171.23 (14)	C210—C21A—C220—C22A	174.12 (14)
C17A—C11A—C120—C121	−178.63 (11)	C27A—C21A—C220—C221	−174.04 (11)
C110—C11A—C120—C121	−6.1 (2)	C210—C21A—C220—C221	−0.8 (2)
C12A—C120—C121—C126	123.80 (14)	C22A—C220—C221—C226	124.61 (14)
C11A—C120—C121—C126	−59.11 (17)	C21A—C220—C221—C226	−60.78 (17)
C12A—C120—C121—C122	−58.94 (18)	C22A—C220—C221—C222	−55.22 (17)
C11A—C120—C121—C122	118.14 (14)	C21A—C220—C221—C222	119.39 (14)
C126—C121—C122—C123	−1.2 (2)	C226—C221—C222—C223	−1.15 (19)
C120—C121—C122—C123	−178.51 (12)	C220—C221—C222—C223	178.68 (12)
C121—C122—C123—C124	0.6 (2)	C221—C222—C223—C224	0.7 (2)
C122—C123—C124—C125	0.6 (2)	C222—C223—C224—C225	0.4 (2)
C122—C123—C124—C127	−178.66 (14)	C222—C223—C224—C227	−178.93 (13)
C123—C124—C125—C126	−1.2 (2)	C223—C224—C225—C226	−1.0 (2)
C127—C124—C125—C126	178.07 (14)	C227—C224—C225—C226	178.33 (13)
C124—C125—C126—C121	0.6 (2)	C222—C221—C226—C225	0.57 (19)
C122—C121—C126—C125	0.6 (2)	C220—C221—C226—C225	−179.26 (12)
C120—C121—C126—C125	177.95 (12)	C224—C225—C226—C221	0.5 (2)
C11A—C120—C12A—C16A	−0.18 (18)	C21A—C220—C22A—C26A	−4.55 (18)
C121—C120—C12A—C16A	176.94 (12)	C221—C220—C22A—C26A	170.32 (12)
C11A—C120—C12A—C12B	179.88 (12)	C21A—C220—C22A—C22B	176.89 (12)
C121—C120—C12A—C12B	−3.0 (2)	C221—C220—C22A—C22B	−8.2 (2)
N17—C16A—C12A—C120	2.42 (19)	N27—C26A—C22A—C220	5.6 (2)
C16—C16A—C12A—C120	−174.63 (12)	C26—C26A—C22A—C220	−171.43 (12)
N17—C16A—C12A—C12B	−177.64 (12)	N27—C26A—C22A—C22B	−175.70 (12)
C16—C16A—C12A—C12B	5.32 (17)	C26—C26A—C22A—C22B	7.24 (18)
C12—C11—C12B—C14A	−1.80 (19)	C22—C21—C22B—C24A	−3.61 (19)
C12—C11—C12B—C12A	−179.41 (12)	C22—C21—C22B—C22A	178.84 (12)
C14—C14A—C12B—C11	2.08 (19)	C24—C24A—C22B—C21	5.36 (19)
C15—C14A—C12B—C11	−174.77 (12)	C25—C24A—C22B—C21	−171.24 (12)
C14—C14A—C12B—C12A	179.79 (12)	C24—C24A—C22B—C22A	−177.00 (12)
C15—C14A—C12B—C12A	2.94 (18)	C25—C24A—C22B—C22A	6.40 (18)
C120—C12A—C12B—C11	−29.9 (2)	C220—C22A—C22B—C21	−34.65 (19)
C16A—C12A—C12B—C11	150.19 (12)	C26A—C22A—C22B—C21	146.75 (13)
C120—C12A—C12B—C14A	152.55 (13)	C220—C22A—C22B—C24A	147.80 (13)
C16A—C12A—C12B—C14A	−27.40 (17)	C26A—C22A—C22B—C24A	−30.80 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···Cg6^i	0.95	2.89	3.662 (2)	136
C122—H122···Cg7	0.95	2.75	3.412 (2)	127
C125—H125···Cg8^ii	0.95	2.87	3.772 (2)	160
C222—H222···Cg9	0.95	2.75	3.322 (2)	119
C225—H225···Cg10^iii	0.95	2.93	3.834 (2)	160

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.

(IX) 11-(4-methoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro- 5H-benzo[f]pyrazolo[3,4-b]quinoline

Crystal data

C28H23N3O	F(000) = 3520
Mr = 417.49	Dx = 1.278 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19715 reflections
a = 18.0854 (3) Å	θ = 3.0–27.5°
b = 21.2296 (5) Å	µ = 0.08 mm^−1
c = 23.8007 (5) Å	T = 120 K
β = 108.258 (1)°	Lath, colourless
V = 8678.1 (3) Å^3	0.90 × 0.30 × 0.10 mm
Z = 16

Data collection

Bruker-Nonius KappaCCD diffractometer	19715 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	8289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.166
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ & ω scans	h = −23→22
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −27→26
Tmin = 0.934, Tmax = 0.992	l = −30→30
99695 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)] = 0.096	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
19715 reflections	(Δ/σ)max < 0.001
1161 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	1.00741 (15)	0.77687 (13)	0.58326 (12)	0.0341 (7)
C12	0.98413 (16)	0.82911 (14)	0.54727 (14)	0.0431 (8)
C13	0.97377 (17)	0.88632 (14)	0.57157 (14)	0.0483 (8)
C14	0.98758 (16)	0.89140 (14)	0.63177 (14)	0.0448 (8)
C14A	1.01138 (14)	0.83941 (13)	0.66848 (12)	0.0332 (7)
C15	1.03120 (15)	0.84432 (12)	0.73444 (12)	0.0367 (7)
C16	1.10624 (14)	0.80866 (12)	0.76321 (12)	0.0335 (7)
C16A	1.09516 (14)	0.74088 (12)	0.74424 (12)	0.0282 (6)
N17	1.12998 (11)	0.69846 (10)	0.78567 (9)	0.0293 (5)
C17A	1.11599 (14)	0.63841 (13)	0.76781 (11)	0.0269 (6)
N18	1.14384 (12)	0.58613 (10)	0.80153 (9)	0.0319 (6)
C181	1.19480 (15)	0.58010 (13)	0.86040 (12)	0.0346 (7)
C182	1.23896 (17)	0.52594 (15)	0.87633 (13)	0.0498 (8)
C183	1.28718 (18)	0.51901 (17)	0.93440 (14)	0.0598 (10)
C184	1.29183 (18)	0.56563 (17)	0.97557 (14)	0.0542 (9)
C185	1.24901 (17)	0.61971 (16)	0.95893 (13)	0.0477 (8)
C186	1.20052 (15)	0.62750 (14)	0.90124 (12)	0.0385 (7)
N19	1.11322 (13)	0.53242 (10)	0.77010 (10)	0.0365 (6)
C110	1.06836 (15)	0.55073 (12)	0.71741 (11)	0.0300 (7)
C111	1.02341 (15)	0.50250 (12)	0.67412 (11)	0.0369 (7)
C11A	1.06866 (14)	0.61779 (12)	0.71247 (11)	0.0261 (6)
C120	1.03341 (13)	0.66284 (12)	0.66895 (11)	0.0253 (6)
C121	0.98514 (14)	0.63964 (11)	0.60980 (11)	0.0245 (6)
C122	0.90573 (14)	0.64941 (12)	0.58749 (11)	0.0280 (6)
C123	0.86207 (14)	0.62503 (12)	0.53299 (11)	0.0297 (7)
C124	0.89869 (15)	0.59023 (12)	0.49981 (11)	0.0300 (7)
O124	0.86229 (10)	0.56352 (9)	0.44608 (7)	0.0395 (5)
C127	0.77964 (15)	0.56804 (14)	0.42293 (12)	0.0456 (8)
C125	0.97852 (14)	0.58127 (12)	0.52145 (11)	0.0297 (6)
C126	1.02093 (14)	0.60467 (12)	0.57579 (11)	0.0276 (6)
C12A	1.04837 (13)	0.72620 (12)	0.68499 (11)	0.0265 (6)
C12B	1.02046 (14)	0.78070 (12)	0.64431 (11)	0.0281 (6)
C21	0.66787 (14)	0.35957 (12)	0.69753 (11)	0.0302 (6)
C22	0.64313 (15)	0.41183 (13)	0.66281 (12)	0.0347 (7)
C23	0.63352 (15)	0.46876 (13)	0.68777 (12)	0.0367 (7)
C24	0.64986 (14)	0.47302 (12)	0.74855 (12)	0.0327 (7)
C24A	0.67546 (14)	0.42042 (13)	0.78465 (11)	0.0288 (6)
C25	0.69849 (15)	0.42512 (12)	0.85102 (11)	0.0341 (7)
C26	0.77180 (15)	0.38637 (12)	0.87772 (11)	0.0327 (7)
C26A	0.75713 (14)	0.31944 (12)	0.85787 (11)	0.0268 (6)
N27	0.78800 (11)	0.27572 (10)	0.89894 (9)	0.0271 (5)
C27A	0.77232 (14)	0.21626 (13)	0.87975 (11)	0.0266 (6)
N28	0.79484 (12)	0.16321 (10)	0.91359 (9)	0.0306 (5)
C281	0.83816 (14)	0.15588 (13)	0.97451 (11)	0.0305 (7)
C282	0.83525 (15)	0.09863 (13)	1.00180 (12)	0.0382 (7)
C283	0.87902 (17)	0.08979 (15)	1.06026 (13)	0.0446 (8)
C284	0.92545 (16)	0.13783 (15)	1.09188 (13)	0.0436 (8)
C285	0.92764 (15)	0.19497 (14)	1.06483 (12)	0.0395 (7)
C286	0.88406 (15)	0.20429 (13)	1.00604 (11)	0.0345 (7)
N29	0.76457 (13)	0.11051 (10)	0.88073 (10)	0.0372 (6)
C210	0.72472 (15)	0.12942 (13)	0.82712 (12)	0.0339 (7)
C211	0.68576 (18)	0.08099 (13)	0.78146 (13)	0.0524 (9)
C21A	0.72712 (14)	0.19671 (12)	0.82320 (11)	0.0267 (6)
C220	0.69308 (14)	0.24345 (12)	0.78049 (11)	0.0252 (6)
C221	0.64050 (14)	0.22418 (12)	0.72115 (11)	0.0250 (6)
C222	0.56272 (14)	0.24247 (12)	0.70157 (11)	0.0285 (6)
C223	0.51414 (14)	0.22522 (12)	0.64587 (11)	0.0302 (7)
C224	0.54350 (14)	0.18907 (13)	0.60937 (11)	0.0313 (7)
O224	0.50175 (10)	0.16956 (9)	0.55337 (8)	0.0421 (5)
C227	0.42471 (15)	0.19283 (15)	0.52890 (11)	0.0472 (8)
C225	0.62082 (15)	0.17007 (13)	0.62857 (12)	0.0376 (7)
C226	0.66837 (15)	0.18781 (12)	0.68358 (11)	0.0342 (7)
C22A	0.71046 (13)	0.30629 (12)	0.79829 (10)	0.0245 (6)
C22B	0.68344 (13)	0.36211 (12)	0.75905 (11)	0.0263 (6)
C31	0.51657 (15)	0.88414 (13)	0.59611 (12)	0.0341 (7)
C32	0.49439 (16)	0.93824 (14)	0.56300 (13)	0.0417 (8)
C33	0.48605 (17)	0.99434 (14)	0.59015 (14)	0.0468 (8)
C34	0.50174 (15)	0.99583 (13)	0.65128 (14)	0.0415 (8)
C34A	0.52449 (14)	0.94154 (13)	0.68507 (12)	0.0323 (7)
C35	0.54609 (15)	0.94297 (12)	0.75123 (11)	0.0354 (7)
C36	0.61947 (15)	0.90412 (11)	0.77744 (11)	0.0331 (7)
C36A	0.60457 (14)	0.83765 (12)	0.75541 (11)	0.0266 (6)
N37	0.63600 (11)	0.79272 (10)	0.79477 (9)	0.0275 (5)
C37A	0.61833 (14)	0.73419 (12)	0.77441 (11)	0.0254 (6)
N38	0.63931 (12)	0.67955 (10)	0.80653 (9)	0.0292 (5)
C381	0.68499 (14)	0.66857 (13)	0.86639 (11)	0.0297 (7)
C382	0.68622 (16)	0.60856 (13)	0.88990 (12)	0.0386 (7)
C383	0.73102 (17)	0.59687 (14)	0.94765 (12)	0.0433 (8)
C384	0.77375 (16)	0.64437 (15)	0.98227 (13)	0.0422 (8)
C385	0.77183 (15)	0.70376 (15)	0.95907 (12)	0.0430 (8)
C386	0.72745 (15)	0.71644 (14)	0.90096 (12)	0.0367 (7)
N39	0.60248 (12)	0.62852 (10)	0.77286 (10)	0.0341 (6)
C310	0.56110 (15)	0.65065 (12)	0.72077 (11)	0.0301 (7)
C311	0.51080 (16)	0.60658 (12)	0.67589 (12)	0.0413 (8)
C31A	0.56981 (13)	0.71743 (12)	0.71819 (11)	0.0247 (6)
C320	0.53844 (13)	0.76520 (12)	0.67657 (11)	0.0240 (6)
C321	0.48690 (14)	0.74555 (11)	0.61645 (11)	0.0245 (6)
C322	0.40793 (14)	0.75840 (11)	0.59672 (10)	0.0264 (6)
C323	0.36069 (14)	0.73730 (12)	0.54184 (11)	0.0294 (6)
C324	0.39281 (14)	0.70241 (12)	0.50619 (11)	0.0281 (6)
O324	0.35200 (10)	0.67856 (9)	0.45186 (7)	0.0392 (5)
C327	0.27383 (14)	0.69774 (14)	0.42595 (11)	0.0424 (8)
C325	0.47151 (14)	0.68903 (12)	0.52530 (11)	0.0327 (7)
C326	0.51822 (14)	0.71012 (12)	0.57969 (11)	0.0298 (7)
C32A	0.55702 (14)	0.82725 (12)	0.69540 (11)	0.0256 (6)
C32B	0.53142 (14)	0.88419 (12)	0.65760 (11)	0.0277 (6)
C41	0.83177 (14)	0.75472 (13)	0.80761 (12)	0.0330 (7)
C42	0.85372 (15)	0.80687 (14)	0.84373 (12)	0.0393 (7)
C43	0.85862 (15)	0.86521 (14)	0.81973 (13)	0.0422 (8)
C44	0.84067 (15)	0.87158 (13)	0.75913 (13)	0.0384 (7)
C44A	0.81909 (14)	0.81973 (13)	0.72203 (12)	0.0315 (7)
C45	0.79793 (15)	0.82619 (13)	0.65602 (11)	0.0372 (7)
C46	0.72750 (14)	0.78486 (12)	0.62703 (11)	0.0342 (7)
C46A	0.74563 (14)	0.71785 (12)	0.64609 (11)	0.0269 (6)
N47	0.71628 (11)	0.67451 (10)	0.60418 (9)	0.0277 (5)
C47A	0.73691 (14)	0.61516 (12)	0.62144 (11)	0.0260 (6)
N48	0.71803 (11)	0.56221 (10)	0.58654 (9)	0.0278 (5)
C481	0.66704 (14)	0.55344 (13)	0.52815 (11)	0.0304 (7)
C482	0.65134 (16)	0.49224 (14)	0.50691 (12)	0.0428 (8)
C483	0.60279 (18)	0.48269 (15)	0.44961 (13)	0.0530 (9)
C484	0.56909 (17)	0.53269 (15)	0.41384 (13)	0.0462 (8)
C485	0.58467 (16)	0.59313 (15)	0.43548 (12)	0.0439 (8)
C486	0.63383 (15)	0.60373 (13)	0.49261 (12)	0.0358 (7)
N49	0.75598 (12)	0.51016 (10)	0.61770 (9)	0.0313 (5)
C410	0.79562 (14)	0.52951 (12)	0.67119 (11)	0.0291 (6)
C411	0.84154 (15)	0.48245 (12)	0.71485 (11)	0.0389 (7)
C41A	0.78514 (13)	0.59607 (12)	0.67671 (11)	0.0262 (6)
C420	0.81369 (13)	0.64205 (12)	0.72099 (10)	0.0247 (6)
C421	0.86213 (14)	0.62013 (12)	0.78058 (11)	0.0252 (6)
C422	0.94078 (14)	0.63338 (12)	0.80292 (11)	0.0304 (7)
C423	0.98573 (15)	0.61046 (12)	0.85775 (11)	0.0327 (7)
C424	0.95112 (14)	0.57399 (13)	0.89096 (11)	0.0307 (7)
O424	0.98921 (10)	0.54886 (9)	0.94533 (7)	0.0391 (5)
C427	1.07127 (15)	0.55918 (14)	0.96887 (12)	0.0441 (8)
C425	0.87197 (15)	0.56124 (13)	0.86938 (11)	0.0351 (7)
C426	0.82856 (15)	0.58380 (12)	0.81480 (11)	0.0330 (7)
C42A	0.79236 (13)	0.70467 (12)	0.70535 (11)	0.0254 (6)
C42B	0.81531 (14)	0.75967 (12)	0.74612 (11)	0.0287 (6)
H11	1.0147	0.7378	0.5663	0.041*
H12	0.9753	0.8257	0.5059	0.052*
H13	0.9572	0.9221	0.5468	0.058*
H14	0.9808	0.9309	0.6483	0.054*
H15A	0.9886	0.8262	0.7472	0.044*
H15B	1.0376	0.8891	0.7466	0.044*
H16A	1.1491	0.8274	0.7512	0.040*
H16B	1.1201	0.8115	0.8068	0.040*
H182	1.2364	0.4939	0.8480	0.060*
H183	1.3172	0.4817	0.9457	0.072*
H184	1.3245	0.5604	1.0152	0.065*
H185	1.2526	0.6521	0.9872	0.057*
H186	1.1714	0.6652	0.8899	0.046*
H11A	1.0462	0.4980	0.6420	0.055*
H11B	0.9691	0.5160	0.6578	0.055*
H11C	1.0256	0.4620	0.6943	0.055*
H122	0.8804	0.6733	0.6099	0.034*
H123	0.8075	0.6321	0.5185	0.036*
H12A	0.7564	0.5513	0.4519	0.068*
H12B	0.7611	0.5436	0.3862	0.068*
H12C	0.7646	0.6123	0.4148	0.068*
H125	1.0042	0.5587	0.4985	0.036*
H126	1.0754	0.5970	0.5905	0.033*
H21	0.6746	0.3209	0.6796	0.036*
H22	0.6325	0.4088	0.6212	0.042*
H23	0.6159	0.5047	0.6635	0.044*
H24	0.6436	0.5122	0.7659	0.039*
H25A	0.6559	0.4090	0.8650	0.041*
H25B	0.7083	0.4697	0.8634	0.041*
H26A	0.8149	0.4038	0.8651	0.039*
H26B	0.7872	0.3884	0.9214	0.039*
H282	0.8033	0.0656	0.9803	0.046*
H283	0.8772	0.0505	1.0789	0.053*
H284	0.9557	0.1315	1.1320	0.052*
H285	0.9591	0.2281	1.0866	0.047*
H286	0.8857	0.2437	0.9875	0.041*
H21A	0.7143	0.0770	0.7528	0.079*
H21B	0.6321	0.0941	0.7610	0.079*
H21C	0.6855	0.0403	0.8009	0.079*
H222	0.5425	0.2672	0.7267	0.034*
H223	0.4612	0.2382	0.6330	0.036*
H27A	0.3932	0.1793	0.5535	0.071*
H27B	0.4020	0.1763	0.4887	0.071*
H27C	0.4258	0.2389	0.5276	0.071*
H225	0.6409	0.1448	0.6037	0.045*
H226	0.7213	0.1749	0.6962	0.041*
H31	0.5219	0.8460	0.5768	0.041*
H32	0.4848	0.9370	0.5214	0.050*
H33	0.4698	1.0314	0.5673	0.056*
H34	0.4969	1.0343	0.6701	0.050*
H35A	0.5031	0.9255	0.7638	0.042*
H35B	0.5553	0.9870	0.7655	0.042*
H36A	0.6628	0.9223	0.7657	0.040*
H36B	0.6344	0.9047	0.8212	0.040*
H382	0.6564	0.5757	0.8664	0.046*
H383	0.7323	0.5557	0.9636	0.052*
H384	0.8044	0.6361	1.0220	0.051*
H385	0.8012	0.7366	0.9830	0.052*
H386	0.7264	0.7577	0.8852	0.044*
H31A	0.5310	0.6029	0.6423	0.062*
H31B	0.4575	0.6229	0.6620	0.062*
H31C	0.5109	0.5650	0.6939	0.062*
H322	0.3855	0.7821	0.6211	0.032*
H323	0.3066	0.7468	0.5289	0.035*
H32A	0.2439	0.6876	0.4527	0.064*
H32B	0.2513	0.6757	0.3883	0.064*
H32C	0.2721	0.7433	0.4189	0.064*
H325	0.4936	0.6651	0.5008	0.039*
H326	0.5722	0.7005	0.5924	0.036*
H41	0.8278	0.7149	0.8247	0.040*
H42	0.8655	0.8025	0.8853	0.047*
H43	0.8743	0.9009	0.8447	0.051*
H44	0.8431	0.9120	0.7426	0.046*
H45A	0.8423	0.8130	0.6428	0.045*
H45B	0.7856	0.8707	0.6444	0.045*
H46A	0.6824	0.7996	0.6386	0.041*
H46B	0.7138	0.7879	0.5834	0.041*
H482	0.6736	0.4574	0.5314	0.051*
H483	0.5926	0.4410	0.4348	0.064*
H484	0.5355	0.5256	0.3748	0.055*
H485	0.5616	0.6279	0.4111	0.053*
H486	0.6445	0.6455	0.5071	0.043*
H41A	0.8131	0.4712	0.7423	0.058*
H41B	0.8921	0.5006	0.7370	0.058*
H41C	0.8496	0.4446	0.6939	0.058*
H422	0.9646	0.6586	0.7804	0.037*
H423	1.0398	0.6197	0.8724	0.039*
H42A	1.0971	0.5416	0.9418	0.066*
H42B	1.0913	0.5386	1.0075	0.066*
H42C	1.0816	0.6045	0.9734	0.066*
H425	0.8478	0.5370	0.8923	0.042*
H426	0.7745	0.5744	0.8002	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0368 (16)	0.0295 (18)	0.0358 (17)	−0.0032 (13)	0.0113 (14)	0.0012 (14)
C12	0.0459 (19)	0.039 (2)	0.0424 (19)	−0.0009 (15)	0.0102 (15)	0.0093 (16)
C13	0.053 (2)	0.032 (2)	0.055 (2)	0.0008 (15)	0.0087 (17)	0.0127 (17)
C14	0.0407 (18)	0.0277 (19)	0.059 (2)	0.0026 (14)	0.0056 (16)	−0.0003 (16)
C14A	0.0258 (15)	0.0254 (18)	0.0430 (18)	−0.0014 (12)	0.0030 (13)	−0.0018 (15)
C15	0.0347 (16)	0.0255 (17)	0.0459 (19)	−0.0018 (13)	0.0067 (14)	−0.0110 (14)
C16	0.0316 (15)	0.0290 (18)	0.0360 (17)	−0.0017 (13)	0.0048 (13)	−0.0083 (13)
C16A	0.0224 (14)	0.0275 (18)	0.0355 (17)	−0.0026 (12)	0.0102 (13)	−0.0012 (14)
N17	0.0277 (12)	0.0264 (14)	0.0325 (13)	−0.0020 (10)	0.0076 (10)	−0.0023 (12)
C17A	0.0250 (14)	0.0263 (17)	0.0286 (16)	0.0015 (12)	0.0074 (12)	0.0012 (13)
N18	0.0342 (13)	0.0302 (14)	0.0251 (13)	−0.0019 (11)	0.0005 (11)	0.0000 (11)
C181	0.0314 (16)	0.0399 (19)	0.0278 (17)	−0.0040 (14)	0.0025 (13)	0.0072 (15)
C182	0.052 (2)	0.049 (2)	0.040 (2)	0.0056 (17)	0.0038 (16)	0.0073 (16)
C183	0.059 (2)	0.062 (3)	0.047 (2)	0.0094 (18)	−0.0010 (18)	0.023 (2)
C184	0.048 (2)	0.070 (3)	0.0329 (19)	−0.0160 (19)	−0.0039 (16)	0.0152 (19)
C185	0.0477 (19)	0.055 (2)	0.0347 (19)	−0.0221 (17)	0.0044 (15)	0.0046 (16)
C186	0.0371 (17)	0.046 (2)	0.0295 (17)	−0.0109 (14)	0.0058 (14)	0.0055 (15)
N19	0.0403 (14)	0.0313 (15)	0.0333 (14)	−0.0032 (11)	0.0050 (12)	0.0013 (12)
C110	0.0315 (16)	0.0288 (18)	0.0286 (16)	−0.0035 (12)	0.0079 (13)	0.0001 (13)
C111	0.0431 (17)	0.0251 (17)	0.0364 (17)	−0.0052 (13)	0.0038 (14)	−0.0008 (14)
C11A	0.0243 (14)	0.0277 (18)	0.0249 (15)	−0.0039 (12)	0.0057 (12)	−0.0037 (13)
C120	0.0199 (13)	0.0302 (18)	0.0252 (15)	−0.0003 (12)	0.0060 (12)	0.0001 (13)
C121	0.0245 (14)	0.0235 (16)	0.0239 (15)	−0.0031 (12)	0.0056 (12)	0.0019 (12)
C122	0.0272 (15)	0.0292 (17)	0.0281 (16)	−0.0024 (12)	0.0095 (13)	−0.0020 (13)
C123	0.0222 (14)	0.0370 (18)	0.0270 (16)	−0.0037 (12)	0.0038 (12)	0.0044 (13)
C124	0.0353 (17)	0.0315 (17)	0.0206 (15)	−0.0064 (13)	0.0051 (13)	0.0013 (13)
O124	0.0343 (11)	0.0556 (14)	0.0238 (11)	−0.0085 (9)	0.0019 (9)	−0.0065 (10)
C127	0.0335 (18)	0.064 (2)	0.0305 (17)	−0.0112 (15)	−0.0019 (14)	−0.0043 (15)
C125	0.0331 (16)	0.0331 (17)	0.0244 (15)	−0.0012 (13)	0.0110 (13)	−0.0020 (13)
C126	0.0243 (14)	0.0298 (17)	0.0270 (16)	−0.0011 (12)	0.0056 (12)	0.0028 (13)
C12A	0.0212 (14)	0.0271 (17)	0.0309 (16)	−0.0007 (12)	0.0080 (12)	−0.0022 (13)
C12B	0.0245 (14)	0.0236 (17)	0.0345 (17)	−0.0029 (12)	0.0066 (13)	0.0016 (13)
C21	0.0358 (16)	0.0263 (17)	0.0296 (16)	−0.0040 (13)	0.0121 (13)	−0.0027 (13)
C22	0.0387 (16)	0.0372 (19)	0.0267 (16)	−0.0018 (14)	0.0082 (13)	0.0041 (14)
C23	0.0360 (16)	0.0337 (19)	0.0370 (18)	−0.0012 (13)	0.0066 (14)	0.0095 (15)
C24	0.0311 (15)	0.0254 (17)	0.0390 (18)	0.0006 (12)	0.0073 (13)	−0.0016 (14)
C24A	0.0251 (14)	0.0330 (18)	0.0271 (15)	−0.0046 (12)	0.0066 (12)	−0.0004 (14)
C25	0.0405 (17)	0.0276 (17)	0.0324 (17)	−0.0017 (13)	0.0086 (14)	−0.0072 (13)
C26	0.0378 (16)	0.0302 (18)	0.0262 (15)	−0.0044 (13)	0.0044 (13)	−0.0051 (13)
C26A	0.0247 (14)	0.0294 (17)	0.0263 (15)	−0.0017 (12)	0.0080 (12)	−0.0031 (13)
N27	0.0268 (12)	0.0266 (14)	0.0265 (13)	−0.0008 (10)	0.0062 (10)	−0.0002 (11)
C27A	0.0246 (14)	0.0293 (18)	0.0269 (16)	0.0023 (12)	0.0094 (12)	0.0015 (14)
N28	0.0318 (13)	0.0291 (15)	0.0274 (13)	−0.0002 (11)	0.0041 (11)	0.0013 (11)
C281	0.0260 (15)	0.0400 (19)	0.0266 (16)	0.0050 (13)	0.0096 (13)	0.0051 (14)
C282	0.0358 (16)	0.040 (2)	0.0362 (18)	0.0005 (14)	0.0083 (14)	0.0083 (15)
C283	0.0494 (19)	0.047 (2)	0.0381 (19)	0.0146 (16)	0.0152 (16)	0.0163 (16)
C284	0.0401 (18)	0.057 (2)	0.0306 (17)	0.0108 (16)	0.0070 (14)	0.0092 (17)
C285	0.0366 (17)	0.048 (2)	0.0298 (17)	0.0056 (15)	0.0051 (14)	0.0006 (15)
C286	0.0309 (15)	0.0405 (19)	0.0312 (17)	0.0056 (14)	0.0083 (13)	0.0044 (14)
N29	0.0405 (14)	0.0282 (15)	0.0376 (15)	−0.0025 (11)	0.0046 (12)	−0.0012 (12)
C210	0.0336 (16)	0.0281 (18)	0.0367 (18)	−0.0027 (13)	0.0063 (14)	−0.0008 (14)
C211	0.064 (2)	0.0295 (19)	0.051 (2)	−0.0072 (16)	−0.0005 (17)	−0.0030 (16)
C21A	0.0253 (14)	0.0263 (18)	0.0281 (16)	−0.0015 (12)	0.0079 (12)	−0.0020 (13)
C220	0.0238 (14)	0.0258 (17)	0.0269 (15)	−0.0003 (12)	0.0092 (12)	−0.0019 (13)
C221	0.0238 (14)	0.0248 (16)	0.0247 (15)	−0.0046 (11)	0.0052 (12)	−0.0014 (12)
C222	0.0299 (16)	0.0309 (17)	0.0269 (16)	−0.0007 (12)	0.0119 (13)	−0.0005 (13)
C223	0.0234 (14)	0.0370 (18)	0.0309 (16)	−0.0018 (12)	0.0097 (13)	0.0012 (13)
C224	0.0302 (16)	0.0345 (18)	0.0263 (16)	−0.0032 (13)	0.0045 (13)	−0.0003 (13)
O224	0.0315 (11)	0.0603 (15)	0.0289 (11)	0.0018 (9)	0.0012 (9)	−0.0095 (10)
C227	0.0299 (17)	0.082 (3)	0.0273 (17)	−0.0027 (16)	0.0050 (14)	−0.0014 (16)
C225	0.0331 (16)	0.045 (2)	0.0331 (17)	0.0051 (13)	0.0083 (14)	−0.0128 (14)
C226	0.0271 (15)	0.0369 (18)	0.0354 (17)	0.0051 (13)	0.0049 (13)	−0.0055 (14)
C22A	0.0228 (14)	0.0273 (17)	0.0249 (15)	0.0003 (12)	0.0095 (12)	0.0019 (13)
C22B	0.0244 (14)	0.0286 (17)	0.0271 (15)	−0.0035 (12)	0.0097 (12)	−0.0018 (13)
C31	0.0387 (16)	0.0297 (18)	0.0345 (17)	−0.0017 (13)	0.0125 (14)	0.0011 (14)
C32	0.0483 (19)	0.038 (2)	0.0370 (18)	−0.0026 (15)	0.0107 (15)	0.0064 (16)
C33	0.055 (2)	0.032 (2)	0.047 (2)	0.0004 (15)	0.0076 (16)	0.0114 (16)
C34	0.0407 (18)	0.0268 (19)	0.052 (2)	0.0023 (14)	0.0080 (15)	0.0005 (16)
C34A	0.0316 (16)	0.0256 (18)	0.0368 (17)	−0.0033 (13)	0.0067 (13)	−0.0022 (14)
C35	0.0407 (17)	0.0293 (18)	0.0319 (17)	0.0002 (13)	0.0055 (14)	−0.0085 (13)
C36	0.0351 (16)	0.0270 (17)	0.0323 (16)	−0.0018 (13)	0.0036 (13)	−0.0057 (13)
C36A	0.0240 (14)	0.0249 (17)	0.0305 (16)	−0.0015 (12)	0.0079 (12)	−0.0027 (13)
N37	0.0280 (12)	0.0251 (14)	0.0280 (13)	0.0007 (10)	0.0069 (10)	−0.0034 (11)
C37A	0.0253 (14)	0.0278 (18)	0.0230 (15)	0.0035 (12)	0.0076 (12)	0.0012 (13)
N38	0.0338 (13)	0.0287 (14)	0.0222 (12)	0.0012 (11)	0.0046 (10)	−0.0005 (11)
C381	0.0256 (14)	0.0383 (19)	0.0243 (16)	0.0025 (13)	0.0068 (12)	0.0013 (14)
C382	0.0505 (19)	0.0343 (19)	0.0303 (17)	0.0079 (14)	0.0114 (15)	0.0033 (14)
C383	0.053 (2)	0.043 (2)	0.0336 (18)	0.0116 (16)	0.0129 (16)	0.0077 (16)
C384	0.0375 (17)	0.055 (2)	0.0304 (17)	0.0088 (16)	0.0055 (14)	0.0100 (17)
C385	0.0360 (17)	0.056 (2)	0.0327 (18)	−0.0087 (15)	0.0041 (14)	0.0008 (16)
C386	0.0328 (16)	0.0413 (19)	0.0333 (17)	−0.0065 (14)	0.0067 (14)	0.0040 (15)
N39	0.0414 (14)	0.0251 (14)	0.0318 (14)	−0.0010 (11)	0.0057 (11)	−0.0020 (12)
C310	0.0335 (16)	0.0279 (18)	0.0283 (16)	0.0017 (13)	0.0088 (13)	0.0011 (13)
C311	0.0519 (19)	0.0260 (18)	0.0376 (18)	−0.0058 (14)	0.0019 (15)	−0.0026 (14)
C31A	0.0253 (14)	0.0230 (17)	0.0257 (15)	−0.0012 (12)	0.0078 (12)	−0.0020 (12)
C320	0.0221 (14)	0.0250 (17)	0.0263 (15)	0.0006 (12)	0.0094 (12)	−0.0024 (13)
C321	0.0263 (15)	0.0230 (16)	0.0243 (15)	−0.0009 (11)	0.0079 (12)	0.0003 (12)
C322	0.0281 (15)	0.0276 (17)	0.0245 (15)	0.0027 (12)	0.0099 (12)	−0.0020 (12)
C323	0.0228 (14)	0.0366 (18)	0.0263 (15)	−0.0006 (12)	0.0041 (12)	−0.0003 (13)
C324	0.0278 (15)	0.0318 (17)	0.0221 (15)	−0.0022 (12)	0.0042 (12)	−0.0033 (13)
O324	0.0311 (11)	0.0524 (14)	0.0274 (11)	0.0015 (9)	−0.0002 (9)	−0.0115 (10)
C327	0.0286 (16)	0.068 (2)	0.0285 (17)	−0.0038 (15)	0.0058 (13)	−0.0035 (15)
C325	0.0297 (16)	0.0369 (18)	0.0320 (16)	0.0032 (13)	0.0103 (13)	−0.0073 (14)
C326	0.0249 (14)	0.0341 (18)	0.0292 (16)	0.0016 (12)	0.0066 (13)	−0.0039 (13)
C32A	0.0249 (14)	0.0251 (17)	0.0264 (15)	−0.0008 (11)	0.0073 (12)	−0.0039 (12)
C32B	0.0263 (14)	0.0248 (17)	0.0313 (16)	−0.0010 (12)	0.0080 (12)	0.0002 (13)
C41	0.0306 (16)	0.0348 (19)	0.0351 (17)	−0.0034 (13)	0.0126 (13)	−0.0059 (14)
C42	0.0393 (17)	0.047 (2)	0.0327 (17)	−0.0059 (15)	0.0123 (14)	−0.0088 (16)
C43	0.0410 (18)	0.042 (2)	0.045 (2)	−0.0120 (15)	0.0153 (15)	−0.0182 (16)
C44	0.0394 (17)	0.0316 (19)	0.0452 (19)	−0.0068 (13)	0.0145 (15)	−0.0073 (15)
C44A	0.0280 (15)	0.0333 (19)	0.0314 (17)	−0.0004 (13)	0.0066 (13)	−0.0037 (14)
C45	0.0431 (18)	0.0293 (18)	0.0359 (18)	−0.0033 (13)	0.0077 (14)	0.0005 (14)
C46	0.0322 (16)	0.0326 (18)	0.0330 (16)	0.0028 (13)	0.0032 (13)	−0.0004 (14)
C46A	0.0225 (14)	0.0307 (18)	0.0267 (16)	0.0003 (12)	0.0067 (12)	−0.0015 (13)
N47	0.0239 (12)	0.0294 (15)	0.0276 (13)	0.0023 (10)	0.0050 (10)	−0.0002 (11)
C47A	0.0251 (14)	0.0263 (17)	0.0257 (15)	−0.0017 (12)	0.0069 (12)	−0.0011 (13)
N48	0.0296 (12)	0.0288 (14)	0.0235 (12)	−0.0012 (10)	0.0060 (10)	−0.0013 (11)
C481	0.0334 (16)	0.0349 (19)	0.0215 (15)	−0.0039 (13)	0.0066 (13)	−0.0029 (14)
C482	0.057 (2)	0.039 (2)	0.0282 (17)	−0.0141 (15)	0.0070 (15)	−0.0018 (15)
C483	0.073 (2)	0.043 (2)	0.0343 (19)	−0.0214 (18)	0.0052 (17)	−0.0106 (16)
C484	0.049 (2)	0.052 (2)	0.0294 (18)	−0.0109 (16)	−0.0001 (15)	−0.0068 (17)
C485	0.0397 (18)	0.052 (2)	0.0313 (18)	0.0076 (15)	−0.0016 (14)	−0.0038 (16)
C486	0.0316 (16)	0.0387 (19)	0.0312 (17)	0.0069 (13)	0.0011 (13)	−0.0070 (14)
N49	0.0365 (13)	0.0275 (14)	0.0290 (13)	0.0014 (11)	0.0089 (11)	0.0003 (11)
C410	0.0298 (15)	0.0296 (18)	0.0284 (16)	−0.0010 (12)	0.0097 (13)	−0.0018 (13)
C411	0.0446 (18)	0.0338 (19)	0.0351 (17)	0.0072 (14)	0.0078 (14)	0.0050 (14)
C41A	0.0243 (14)	0.0288 (18)	0.0254 (15)	−0.0007 (12)	0.0074 (12)	0.0008 (13)
C420	0.0198 (13)	0.0305 (17)	0.0235 (15)	−0.0012 (12)	0.0065 (11)	−0.0008 (13)
C421	0.0242 (14)	0.0268 (17)	0.0237 (15)	−0.0014 (11)	0.0062 (12)	−0.0016 (12)
C422	0.0283 (15)	0.0366 (18)	0.0254 (16)	−0.0014 (12)	0.0070 (13)	0.0035 (13)
C423	0.0243 (15)	0.0401 (19)	0.0296 (16)	−0.0033 (13)	0.0024 (13)	0.0009 (14)
C424	0.0298 (16)	0.0350 (18)	0.0235 (15)	0.0022 (13)	0.0030 (13)	0.0028 (13)
O424	0.0344 (11)	0.0508 (13)	0.0261 (11)	−0.0051 (9)	0.0007 (9)	0.0122 (9)
C427	0.0379 (18)	0.051 (2)	0.0339 (17)	−0.0015 (14)	−0.0027 (14)	0.0118 (15)
C425	0.0342 (16)	0.0416 (19)	0.0292 (17)	−0.0071 (13)	0.0097 (13)	0.0057 (14)
C426	0.0276 (15)	0.0384 (18)	0.0305 (16)	−0.0057 (13)	0.0056 (13)	−0.0003 (14)
C42A	0.0199 (13)	0.0318 (18)	0.0248 (15)	−0.0016 (12)	0.0074 (12)	−0.0050 (13)
C42B	0.0231 (14)	0.0330 (18)	0.0280 (16)	−0.0038 (12)	0.0050 (12)	−0.0054 (13)

Geometric parameters (Å, º)

C11—C12	1.384 (4)	C31—C32	1.380 (4)
C11—C12B	1.400 (3)	C31—C32B	1.403 (3)
C11—H11	0.95	C31—H31	0.95
C12—C13	1.383 (4)	C32—C33	1.385 (4)
C12—H12	0.95	C32—H32	0.95
C13—C14	1.379 (4)	C33—C34	1.393 (4)
C13—H13	0.95	C33—H33	0.95
C14—C14A	1.390 (4)	C34—C34A	1.392 (4)
C14—H14	0.95	C34—H34	0.95
C14A—C12B	1.404 (3)	C34A—C32B	1.406 (3)
C14A—C15	1.500 (4)	C34A—C35	1.499 (3)
C15—C16	1.517 (3)	C35—C36	1.521 (3)
C15—H15A	0.99	C35—H35A	0.99
C15—H15B	0.99	C35—H35B	0.99
C16—C16A	1.503 (3)	C36—C36A	1.500 (3)
C16—H16A	0.99	C36—H36A	0.99
C16—H16B	0.99	C36—H36B	0.99
C16A—N17	1.338 (3)	C36A—N37	1.333 (3)
C16A—C12A	1.433 (3)	C36A—C32A	1.435 (3)
N17—C17A	1.343 (3)	N37—C37A	1.336 (3)
C17A—N18	1.370 (3)	C37A—N38	1.376 (3)
C17A—C11A	1.398 (3)	C37A—C31A	1.397 (3)
N18—N19	1.381 (3)	N38—N39	1.387 (3)
N18—C181	1.421 (3)	N38—C381	1.424 (3)
C181—C186	1.380 (4)	C381—C386	1.380 (3)
C181—C182	1.383 (4)	C381—C382	1.389 (3)
C182—C183	1.392 (4)	C382—C383	1.382 (3)
C182—H182	0.95	C382—H382	0.95
C183—C184	1.377 (4)	C383—C384	1.376 (4)
C183—H183	0.95	C383—H383	0.95
C184—C185	1.372 (4)	C384—C385	1.372 (4)
C184—H184	0.95	C384—H384	0.95
C185—C186	1.388 (4)	C385—C386	1.391 (3)
C185—H185	0.95	C385—H385	0.95
C186—H186	0.95	C386—H386	0.95
N19—C110	1.321 (3)	N39—C310	1.318 (3)
C110—C11A	1.429 (3)	C310—C31A	1.430 (3)
C110—C111	1.499 (3)	C310—C311	1.495 (3)
C111—H11A	0.98	C311—H31A	0.98
C111—H11B	0.98	C311—H31B	0.98
C111—H11C	0.98	C311—H31C	0.98
C11A—C120	1.407 (3)	C31A—C320	1.407 (3)
C120—C12A	1.401 (3)	C320—C32A	1.398 (3)
C120—C121	1.489 (3)	C320—C321	1.501 (3)
C121—C122	1.382 (3)	C321—C322	1.384 (3)
C121—C126	1.398 (3)	C321—C326	1.401 (3)
C122—C123	1.390 (3)	C322—C323	1.392 (3)
C122—H122	0.95	C322—H322	0.95
C123—C124	1.391 (3)	C323—C324	1.384 (3)
C123—H123	0.95	C323—H323	0.95
C124—O124	1.365 (3)	C324—O324	1.369 (3)
C124—C125	1.386 (3)	C324—C325	1.381 (3)
O124—C127	1.425 (3)	O324—C327	1.414 (3)
C127—H12A	0.98	C327—H32A	0.98
C127—H12B	0.98	C327—H32B	0.98
C127—H12C	0.98	C327—H32C	0.98
C125—C126	1.373 (3)	C325—C326	1.380 (3)
C125—H125	0.95	C325—H325	0.95
C126—H126	0.95	C326—H326	0.95
C12A—C12B	1.492 (3)	C32A—C32B	1.491 (3)
C21—C22	1.372 (3)	C41—C42	1.381 (3)
C21—C22B	1.403 (3)	C41—C42B	1.403 (3)
C21—H21	0.95	C41—H41	0.95
C22—C23	1.381 (4)	C42—C43	1.378 (4)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.386 (3)	C43—C44	1.382 (4)
C23—H23	0.95	C43—H43	0.95
C24—C24A	1.397 (3)	C44—C44A	1.388 (4)
C24—H24	0.95	C44—H44	0.95
C24A—C22B	1.407 (3)	C44A—C42B	1.408 (4)
C24A—C25	1.505 (3)	C44A—C45	1.502 (3)
C25—C26	1.520 (3)	C45—C46	1.522 (3)
C25—H25A	0.99	C45—H45A	0.99
C25—H25B	0.99	C45—H45B	0.99
C26—C26A	1.495 (3)	C46—C46A	1.498 (3)
C26—H26A	0.99	C46—H46A	0.99
C26—H26B	0.99	C46—H46B	0.99
C26A—N27	1.337 (3)	C46A—N47	1.338 (3)
C26A—C22A	1.432 (3)	C46A—C42A	1.426 (3)
N27—C27A	1.342 (3)	N47—C47A	1.342 (3)
C27A—N28	1.370 (3)	C47A—N48	1.376 (3)
C27A—C21A	1.401 (3)	C47A—C41A	1.392 (3)
N28—N29	1.376 (3)	N48—N49	1.387 (3)
N28—C281	1.424 (3)	N48—C481	1.419 (3)
C281—C286	1.385 (4)	C481—C486	1.378 (3)
C281—C282	1.387 (3)	C481—C482	1.391 (4)
C282—C283	1.381 (4)	C482—C483	1.386 (4)
C282—H282	0.95	C482—H482	0.95
C283—C284	1.384 (4)	C483—C484	1.378 (4)
C283—H283	0.95	C483—H483	0.95
C284—C285	1.380 (4)	C484—C485	1.378 (4)
C284—H284	0.95	C484—H484	0.95
C285—C286	1.388 (3)	C485—C486	1.390 (3)
C285—H285	0.95	C485—H485	0.95
C286—H286	0.95	C486—H486	0.95
N29—C210	1.316 (3)	N49—C410	1.316 (3)
C210—C21A	1.433 (3)	C410—C41A	1.437 (3)
C210—C211	1.502 (4)	C410—C411	1.492 (3)
C211—H21A	0.98	C411—H41A	0.98
C211—H21B	0.98	C411—H41B	0.98
C211—H21C	0.98	C411—H41C	0.98
C21A—C220	1.416 (3)	C41A—C420	1.411 (3)
C220—C22A	1.405 (3)	C420—C42A	1.402 (3)
C220—C221	1.492 (3)	C420—C421	1.489 (3)
C221—C226	1.390 (3)	C421—C422	1.383 (3)
C221—C222	1.391 (3)	C421—C426	1.392 (3)
C222—C223	1.391 (3)	C422—C423	1.391 (3)
C222—H222	0.95	C422—H422	0.95
C223—C224	1.384 (3)	C423—C424	1.388 (3)
C223—H223	0.95	C423—H423	0.95
C224—O224	1.374 (3)	C424—O424	1.369 (3)
C224—C225	1.388 (3)	C424—C425	1.388 (3)
O224—C227	1.420 (3)	O424—C427	1.429 (3)
C227—H27A	0.98	C427—H42A	0.98
C227—H27B	0.98	C427—H42B	0.98
C227—H27C	0.98	C427—H42C	0.98
C225—C226	1.375 (3)	C425—C426	1.376 (3)
C225—H225	0.95	C425—H425	0.95
C226—H226	0.95	C426—H426	0.95
C22A—C22B	1.493 (3)	C42A—C42B	1.492 (3)
C12—C11—C12B	121.0 (3)	C32—C31—C32B	121.4 (3)
C12—C11—H11	119.5	C32—C31—H31	119.3
C12B—C11—H11	119.5	C32B—C31—H31	119.3
C13—C12—C11	120.0 (3)	C31—C32—C33	120.3 (3)
C13—C12—H12	120.0	C31—C32—H32	119.9
C11—C12—H12	120.0	C33—C32—H32	119.9
C14—C13—C12	119.9 (3)	C32—C33—C34	119.4 (3)
C14—C13—H13	120.0	C32—C33—H33	120.3
C12—C13—H13	120.0	C34—C33—H33	120.3
C13—C14—C14A	120.7 (3)	C34A—C34—C33	120.8 (3)
C13—C14—H14	119.6	C34A—C34—H34	119.6
C14A—C14—H14	119.6	C33—C34—H34	119.6
C14—C14A—C12B	120.0 (3)	C34—C34A—C32B	120.1 (3)
C14—C14A—C15	121.9 (3)	C34—C34A—C35	121.5 (3)
C12B—C14A—C15	118.0 (2)	C32B—C34A—C35	118.3 (2)
C14A—C15—C16	108.9 (2)	C34A—C35—C36	109.1 (2)
C14A—C15—H15A	109.9	C34A—C35—H35A	109.9
C16—C15—H15A	109.9	C36—C35—H35A	109.9
C14A—C15—H15B	109.9	C34A—C35—H35B	109.9
C16—C15—H15B	109.9	C36—C35—H35B	109.9
H15A—C15—H15B	108.3	H35A—C35—H35B	108.3
C16A—C16—C15	109.0 (2)	C36A—C36—C35	109.2 (2)
C16A—C16—H16A	109.9	C36A—C36—H36A	109.8
C15—C16—H16A	109.9	C35—C36—H36A	109.8
C16A—C16—H16B	109.9	C36A—C36—H36B	109.8
C15—C16—H16B	109.9	C35—C36—H36B	109.8
H16A—C16—H16B	108.3	H36A—C36—H36B	108.3
N17—C16A—C12A	125.1 (2)	N37—C36A—C32A	125.5 (2)
N17—C16A—C16	115.8 (2)	N37—C36A—C36	115.9 (2)
C12A—C16A—C16	119.1 (2)	C32A—C36A—C36	118.6 (2)
C16A—N17—C17A	114.0 (2)	C36A—N37—C37A	114.2 (2)
N17—C17A—N18	125.8 (2)	N37—C37A—N38	126.1 (2)
N17—C17A—C11A	126.5 (2)	N37—C37A—C31A	126.3 (2)
N18—C17A—C11A	107.6 (2)	N38—C37A—C31A	107.4 (2)
C17A—N18—N19	109.9 (2)	C37A—N38—N39	109.8 (2)
C17A—N18—C181	131.0 (2)	C37A—N38—C381	131.8 (2)
N19—N18—C181	119.1 (2)	N39—N38—C381	118.2 (2)
C186—C181—C182	120.2 (3)	C386—C381—C382	120.0 (2)
C186—C181—N18	120.7 (3)	C386—C381—N38	121.1 (2)
C182—C181—N18	119.0 (3)	C382—C381—N38	118.9 (2)
C181—C182—C183	119.2 (3)	C383—C382—C381	119.7 (3)
C181—C182—H182	120.4	C383—C382—H382	120.1
C183—C182—H182	120.4	C381—C382—H382	120.1
C184—C183—C182	120.7 (3)	C384—C383—C382	120.5 (3)
C184—C183—H183	119.7	C384—C383—H383	119.7
C182—C183—H183	119.7	C382—C383—H383	119.7
C185—C184—C183	119.5 (3)	C385—C384—C383	119.6 (3)
C185—C184—H184	120.2	C385—C384—H384	120.2
C183—C184—H184	120.2	C383—C384—H384	120.2
C184—C185—C186	120.6 (3)	C384—C385—C386	120.8 (3)
C184—C185—H185	119.7	C384—C385—H385	119.6
C186—C185—H185	119.7	C386—C385—H385	119.6
C181—C186—C185	119.6 (3)	C381—C386—C385	119.4 (3)
C181—C186—H186	120.2	C381—C386—H386	120.3
C185—C186—H186	120.2	C385—C386—H386	120.3
C110—N19—N18	107.1 (2)	C310—N39—N38	107.1 (2)
N19—C110—C11A	110.8 (2)	N39—C310—C31A	110.9 (2)
N19—C110—C111	119.4 (2)	N39—C310—C311	119.2 (2)
C11A—C110—C111	129.8 (2)	C31A—C310—C311	129.8 (2)
C110—C111—H11A	109.5	C310—C311—H31A	109.5
C110—C111—H11B	109.5	C310—C311—H31B	109.5
H11A—C111—H11B	109.5	H31A—C311—H31B	109.5
C110—C111—H11C	109.5	C310—C311—H31C	109.5
H11A—C111—H11C	109.5	H31A—C311—H31C	109.5
H11B—C111—H11C	109.5	H31B—C311—H31C	109.5
C17A—C11A—C120	118.9 (2)	C37A—C31A—C320	119.0 (2)
C17A—C11A—C110	104.6 (2)	C37A—C31A—C310	104.8 (2)
C120—C11A—C110	136.5 (2)	C320—C31A—C310	136.0 (2)
C12A—C120—C11A	116.6 (2)	C32A—C320—C31A	116.7 (2)
C12A—C120—C121	125.5 (2)	C32A—C320—C321	125.6 (2)
C11A—C120—C121	117.9 (2)	C31A—C320—C321	117.6 (2)
C122—C121—C126	118.1 (2)	C322—C321—C326	118.0 (2)
C122—C121—C120	123.0 (2)	C322—C321—C320	122.4 (2)
C126—C121—C120	118.9 (2)	C326—C321—C320	119.5 (2)
C121—C122—C123	121.4 (2)	C321—C322—C323	121.3 (2)
C121—C122—H122	119.3	C321—C322—H322	119.3
C123—C122—H122	119.3	C323—C322—H322	119.3
C122—C123—C124	119.7 (2)	C324—C323—C322	119.7 (2)
C122—C123—H123	120.2	C324—C323—H323	120.2
C124—C123—H123	120.2	C322—C323—H323	120.2
O124—C124—C125	115.6 (2)	O324—C324—C325	115.5 (2)
O124—C124—C123	125.2 (2)	O324—C324—C323	124.8 (2)
C125—C124—C123	119.2 (2)	C325—C324—C323	119.7 (2)
C124—O124—C127	118.3 (2)	C324—O324—C327	118.4 (2)
O124—C127—H12A	109.5	O324—C327—H32A	109.5
O124—C127—H12B	109.5	O324—C327—H32B	109.5
H12A—C127—H12B	109.5	H32A—C327—H32B	109.5
O124—C127—H12C	109.5	O324—C327—H32C	109.5
H12A—C127—H12C	109.5	H32A—C327—H32C	109.5
H12B—C127—H12C	109.5	H32B—C327—H32C	109.5
C126—C125—C124	120.7 (2)	C326—C325—C324	120.5 (2)
C126—C125—H125	119.7	C326—C325—H325	119.8
C124—C125—H125	119.7	C324—C325—H325	119.8
C125—C126—C121	120.9 (2)	C325—C326—C321	120.8 (2)
C125—C126—H126	119.5	C325—C326—H326	119.6
C121—C126—H126	119.5	C321—C326—H326	119.6
C120—C12A—C16A	118.7 (2)	C320—C32A—C36A	118.2 (2)
C120—C12A—C12B	124.8 (2)	C320—C32A—C32B	124.9 (2)
C16A—C12A—C12B	116.5 (2)	C36A—C32A—C32B	116.9 (2)
C11—C12B—C14A	118.3 (2)	C31—C32B—C34A	118.0 (2)
C11—C12B—C12A	122.8 (2)	C31—C32B—C32A	123.4 (2)
C14A—C12B—C12A	118.8 (2)	C34A—C32B—C32A	118.5 (2)
C22—C21—C22B	121.2 (3)	C42—C41—C42B	121.0 (3)
C22—C21—H21	119.4	C42—C41—H41	119.5
C22B—C21—H21	119.4	C42B—C41—H41	119.5
C21—C22—C23	120.6 (3)	C43—C42—C41	120.4 (3)
C21—C22—H22	119.7	C43—C42—H42	119.8
C23—C22—H22	119.7	C41—C42—H42	119.8
C22—C23—C24	119.5 (3)	C42—C43—C44	119.7 (3)
C22—C23—H23	120.3	C42—C43—H43	120.1
C24—C23—H23	120.3	C44—C43—H43	120.1
C23—C24—C24A	120.7 (3)	C43—C44—C44A	120.9 (3)
C23—C24—H24	119.6	C43—C44—H44	119.6
C24A—C24—H24	119.6	C44A—C44—H44	119.6
C24—C24A—C22B	119.8 (2)	C44—C44A—C42B	119.9 (3)
C24—C24A—C25	121.5 (2)	C44—C44A—C45	121.4 (3)
C22B—C24A—C25	118.7 (2)	C42B—C44A—C45	118.6 (2)
C24A—C25—C26	108.7 (2)	C44A—C45—C46	108.9 (2)
C24A—C25—H25A	109.9	C44A—C45—H45A	109.9
C26—C25—H25A	109.9	C46—C45—H45A	109.9
C24A—C25—H25B	109.9	C44A—C45—H45B	109.9
C26—C25—H25B	109.9	C46—C45—H45B	109.9
H25A—C25—H25B	108.3	H45A—C45—H45B	108.3
C26A—C26—C25	109.7 (2)	C46A—C46—C45	109.7 (2)
C26A—C26—H26A	109.7	C46A—C46—H46A	109.7
C25—C26—H26A	109.7	C45—C46—H46A	109.7
C26A—C26—H26B	109.7	C46A—C46—H46B	109.7
C25—C26—H26B	109.7	C45—C46—H46B	109.7
H26A—C26—H26B	108.2	H46A—C46—H46B	108.2
N27—C26A—C22A	124.8 (2)	N47—C46A—C42A	125.2 (2)
N27—C26A—C26	115.9 (2)	N47—C46A—C46	115.4 (2)
C22A—C26A—C26	119.3 (2)	C42A—C46A—C46	119.4 (2)
C26A—N27—C27A	114.1 (2)	C46A—N47—C47A	114.2 (2)
N27—C27A—N28	125.5 (2)	N47—C47A—N48	126.2 (2)
N27—C27A—C21A	127.1 (2)	N47—C47A—C41A	126.5 (2)
N28—C27A—C21A	107.3 (2)	N48—C47A—C41A	107.2 (2)
C27A—N28—N29	110.0 (2)	C47A—N48—N49	109.90 (19)
C27A—N28—C281	131.0 (2)	C47A—N48—C481	131.4 (2)
N29—N28—C281	118.9 (2)	N49—N48—C481	118.7 (2)
C286—C281—C282	120.0 (2)	C486—C481—C482	120.0 (2)
C286—C281—N28	121.0 (2)	C486—C481—N48	121.6 (2)
C282—C281—N28	118.9 (2)	C482—C481—N48	118.3 (2)
C283—C282—C281	119.8 (3)	C483—C482—C481	119.2 (3)
C283—C282—H282	120.1	C483—C482—H482	120.4
C281—C282—H282	120.1	C481—C482—H482	120.4
C282—C283—C284	120.4 (3)	C484—C483—C482	121.1 (3)
C282—C283—H283	119.8	C484—C483—H483	119.5
C284—C283—H283	119.8	C482—C483—H483	119.5
C285—C284—C283	119.7 (3)	C483—C484—C485	119.2 (3)
C285—C284—H284	120.2	C483—C484—H484	120.4
C283—C284—H284	120.2	C485—C484—H484	120.4
C284—C285—C286	120.4 (3)	C484—C485—C486	120.6 (3)
C284—C285—H285	119.8	C484—C485—H485	119.7
C286—C285—H285	119.8	C486—C485—H485	119.7
C281—C286—C285	119.7 (3)	C481—C486—C485	119.8 (3)
C281—C286—H286	120.2	C481—C486—H486	120.1
C285—C286—H286	120.2	C485—C486—H486	120.1
C210—N29—N28	107.6 (2)	C410—N49—N48	107.3 (2)
N29—C210—C21A	110.4 (2)	N49—C410—C41A	110.4 (2)
N29—C210—C211	118.9 (2)	N49—C410—C411	118.7 (2)
C21A—C210—C211	130.7 (2)	C41A—C410—C411	130.9 (2)
C210—C211—H21A	109.5	C410—C411—H41A	109.5
C210—C211—H21B	109.5	C410—C411—H41B	109.5
H21A—C211—H21B	109.5	H41A—C411—H41B	109.5
C210—C211—H21C	109.5	C410—C411—H41C	109.5
H21A—C211—H21C	109.5	H41A—C411—H41C	109.5
H21B—C211—H21C	109.5	H41B—C411—H41C	109.5
C27A—C21A—C220	118.3 (2)	C47A—C41A—C420	118.6 (2)
C27A—C21A—C210	104.7 (2)	C47A—C41A—C410	105.2 (2)
C220—C21A—C210	136.9 (2)	C420—C41A—C410	136.1 (2)
C22A—C220—C21A	116.3 (2)	C42A—C420—C41A	116.9 (2)
C22A—C220—C221	124.2 (2)	C42A—C420—C421	125.5 (2)
C21A—C220—C221	119.5 (2)	C41A—C420—C421	117.6 (2)
C226—C221—C222	118.2 (2)	C422—C421—C426	118.2 (2)
C226—C221—C220	120.6 (2)	C422—C421—C420	122.0 (2)
C222—C221—C220	121.2 (2)	C426—C421—C420	119.8 (2)
C223—C222—C221	121.1 (2)	C421—C422—C423	121.2 (2)
C223—C222—H222	119.5	C421—C422—H422	119.4
C221—C222—H222	119.5	C423—C422—H422	119.4
C224—C223—C222	119.5 (2)	C424—C423—C422	119.6 (2)
C224—C223—H223	120.2	C424—C423—H423	120.2
C222—C223—H223	120.2	C422—C423—H423	120.2
O224—C224—C223	125.0 (2)	O424—C424—C425	115.4 (2)
O224—C224—C225	115.0 (2)	O424—C424—C423	124.9 (2)
C223—C224—C225	120.0 (2)	C425—C424—C423	119.7 (2)
C224—O224—C227	117.6 (2)	C424—O424—C427	117.6 (2)
O224—C227—H27A	109.5	O424—C427—H42A	109.5
O224—C227—H27B	109.5	O424—C427—H42B	109.5
H27A—C227—H27B	109.5	H42A—C427—H42B	109.5
O224—C227—H27C	109.5	O424—C427—H42C	109.5
H27A—C227—H27C	109.5	H42A—C427—H42C	109.5
H27B—C227—H27C	109.5	H42B—C427—H42C	109.5
C226—C225—C224	119.9 (3)	C426—C425—C424	119.9 (3)
C226—C225—H225	120.0	C426—C425—H425	120.0
C224—C225—H225	120.0	C424—C425—H425	120.0
C225—C226—C221	121.3 (2)	C425—C426—C421	121.4 (2)
C225—C226—H226	119.3	C425—C426—H426	119.3
C221—C226—H226	119.3	C421—C426—H426	119.3
C220—C22A—C26A	119.4 (2)	C420—C42A—C46A	118.5 (2)
C220—C22A—C22B	124.5 (2)	C420—C42A—C42B	124.9 (2)
C26A—C22A—C22B	116.1 (2)	C46A—C42A—C42B	116.6 (2)
C21—C22B—C24A	118.1 (2)	C41—C42B—C44A	118.1 (2)
C21—C22B—C22A	122.8 (2)	C41—C42B—C42A	123.0 (2)
C24A—C22B—C22A	119.0 (2)	C44A—C42B—C42A	118.9 (2)
C12B—C11—C12—C13	0.3 (4)	C32B—C31—C32—C33	−0.2 (4)
C11—C12—C13—C14	0.8 (4)	C31—C32—C33—C34	1.2 (4)
C12—C13—C14—C14A	−0.5 (4)	C32—C33—C34—C34A	−0.9 (4)
C13—C14—C14A—C12B	−1.0 (4)	C33—C34—C34A—C32B	−0.4 (4)
C13—C14—C14A—C15	176.5 (3)	C33—C34—C34A—C35	176.4 (3)
C14—C14A—C15—C16	−134.8 (3)	C34—C34A—C35—C36	−135.8 (3)
C12B—C14A—C15—C16	42.7 (3)	C32B—C34A—C35—C36	41.1 (3)
C14A—C15—C16—C16A	−59.6 (3)	C34A—C35—C36—C36A	−59.5 (3)
C15—C16—C16A—N17	−142.4 (2)	C35—C36—C36A—N37	−140.8 (2)
C15—C16—C16A—C12A	36.6 (3)	C35—C36—C36A—C32A	37.7 (3)
C12A—C16A—N17—C17A	−1.7 (4)	C32A—C36A—N37—C37A	−1.5 (4)
C16—C16A—N17—C17A	177.3 (2)	C36—C36A—N37—C37A	176.9 (2)
C16A—N17—C17A—N18	−179.4 (2)	C36A—N37—C37A—N38	−176.1 (2)
C16A—N17—C17A—C11A	−1.6 (4)	C36A—N37—C37A—C31A	−2.0 (4)
N17—C17A—N18—N19	175.8 (2)	N37—C37A—N38—N39	172.5 (2)
C11A—C17A—N18—N19	−2.3 (3)	C31A—C37A—N38—N39	−2.6 (3)
N17—C17A—N18—C181	−2.8 (4)	N37—C37A—N38—C381	−2.2 (4)
C11A—C17A—N18—C181	179.0 (2)	C31A—C37A—N38—C381	−177.3 (2)
C17A—N18—C181—C186	26.4 (4)	C37A—N38—C381—C386	−10.2 (4)
N19—N18—C181—C186	−152.1 (2)	N39—N38—C381—C386	175.4 (2)
C17A—N18—C181—C182	−153.5 (3)	C37A—N38—C381—C382	169.6 (2)
N19—N18—C181—C182	28.0 (4)	N39—N38—C381—C382	−4.7 (3)
C186—C181—C182—C183	2.1 (4)	C386—C381—C382—C383	−1.0 (4)
N18—C181—C182—C183	−178.1 (3)	N38—C381—C382—C383	179.2 (2)
C181—C182—C183—C184	−0.7 (5)	C381—C382—C383—C384	0.7 (4)
C182—C183—C184—C185	−0.7 (5)	C382—C383—C384—C385	−0.1 (4)
C183—C184—C185—C186	0.7 (5)	C383—C384—C385—C386	−0.2 (4)
C182—C181—C186—C185	−2.0 (4)	C382—C381—C386—C385	0.7 (4)
N18—C181—C186—C185	178.1 (2)	N38—C381—C386—C385	−179.5 (2)
C184—C185—C186—C181	0.6 (4)	C384—C385—C386—C381	0.0 (4)
C17A—N18—N19—C110	1.2 (3)	C37A—N38—N39—C310	1.3 (3)
C181—N18—N19—C110	180.0 (2)	C381—N38—N39—C310	176.8 (2)
N18—N19—C110—C11A	0.4 (3)	N38—N39—C310—C31A	0.5 (3)
N18—N19—C110—C111	−176.8 (2)	N38—N39—C310—C311	−176.4 (2)
N17—C17A—C11A—C120	2.7 (4)	N37—C37A—C31A—C320	3.5 (4)
N18—C17A—C11A—C120	−179.2 (2)	N38—C37A—C31A—C320	178.6 (2)
N17—C17A—C11A—C110	−175.6 (2)	N37—C37A—C31A—C310	−172.3 (2)
N18—C17A—C11A—C110	2.5 (3)	N38—C37A—C31A—C310	2.7 (3)
N19—C110—C11A—C17A	−1.8 (3)	N39—C310—C31A—C37A	−2.0 (3)
C111—C110—C11A—C17A	175.0 (3)	C311—C310—C31A—C37A	174.4 (3)
N19—C110—C11A—C120	−179.7 (3)	N39—C310—C31A—C320	−176.8 (3)
C111—C110—C11A—C120	−2.9 (5)	C311—C310—C31A—C320	−0.4 (5)
C17A—C11A—C120—C12A	−0.5 (3)	C37A—C31A—C320—C32A	−1.5 (3)
C110—C11A—C120—C12A	177.2 (3)	C310—C31A—C320—C32A	172.7 (3)
C17A—C11A—C120—C121	178.2 (2)	C37A—C31A—C320—C321	179.6 (2)
C110—C11A—C120—C121	−4.1 (4)	C310—C31A—C320—C321	−6.1 (4)
C12A—C120—C121—C122	−67.0 (3)	C32A—C320—C321—C322	−66.9 (3)
C11A—C120—C121—C122	114.5 (3)	C31A—C320—C321—C322	111.9 (3)
C12A—C120—C121—C126	115.1 (3)	C32A—C320—C321—C326	116.5 (3)
C11A—C120—C121—C126	−63.5 (3)	C31A—C320—C321—C326	−64.8 (3)
C126—C121—C122—C123	0.4 (4)	C326—C321—C322—C323	−0.4 (4)
C120—C121—C122—C123	−177.6 (2)	C320—C321—C322—C323	−177.1 (2)
C121—C122—C123—C124	−0.3 (4)	C321—C322—C323—C324	0.4 (4)
C122—C123—C124—O124	179.5 (2)	C322—C323—C324—O324	179.1 (2)
C122—C123—C124—C125	−0.9 (4)	C322—C323—C324—C325	−0.2 (4)
C125—C124—O124—C127	176.6 (2)	C325—C324—O324—C327	−171.2 (2)
C123—C124—O124—C127	−3.8 (4)	C323—C324—O324—C327	9.4 (4)
O124—C124—C125—C126	−178.3 (2)	O324—C324—C325—C326	−179.3 (2)
C123—C124—C125—C126	2.0 (4)	C323—C324—C325—C326	0.1 (4)
C124—C125—C126—C121	−1.9 (4)	C324—C325—C326—C321	−0.2 (4)
C122—C121—C126—C125	0.7 (4)	C322—C321—C326—C325	0.3 (4)
C120—C121—C126—C125	178.8 (2)	C320—C321—C326—C325	177.1 (2)
C11A—C120—C12A—C16A	−2.4 (3)	C31A—C320—C32A—C36A	−1.4 (3)
C121—C120—C12A—C16A	179.0 (2)	C321—C320—C32A—C36A	177.3 (2)
C11A—C120—C12A—C12B	176.2 (2)	C31A—C320—C32A—C32B	178.2 (2)
C121—C120—C12A—C12B	−2.4 (4)	C321—C320—C32A—C32B	−3.0 (4)
N17—C16A—C12A—C120	3.8 (4)	N37—C36A—C32A—C320	3.2 (4)
C16—C16A—C12A—C120	−175.2 (2)	C36—C36A—C32A—C320	−175.1 (2)
N17—C16A—C12A—C12B	−175.0 (2)	N37—C36A—C32A—C32B	−176.5 (2)
C16—C16A—C12A—C12B	6.1 (3)	C36—C36A—C32A—C32B	5.2 (3)
C12—C11—C12B—C14A	−1.7 (4)	C32—C31—C32B—C34A	−1.2 (4)
C12—C11—C12B—C12A	−177.7 (2)	C32—C31—C32B—C32A	−178.8 (2)
C14—C14A—C12B—C11	2.0 (4)	C34—C34A—C32B—C31	1.5 (4)
C15—C14A—C12B—C11	−175.5 (2)	C35—C34A—C32B—C31	−175.5 (2)
C14—C14A—C12B—C12A	178.2 (2)	C34—C34A—C32B—C32A	179.2 (2)
C15—C14A—C12B—C12A	0.6 (3)	C35—C34A—C32B—C32A	2.2 (3)
C120—C12A—C12B—C11	−29.1 (4)	C320—C32A—C32B—C31	−29.1 (4)
C16A—C12A—C12B—C11	149.5 (2)	C36A—C32A—C32B—C31	150.6 (2)
C120—C12A—C12B—C14A	154.9 (2)	C320—C32A—C32B—C34A	153.4 (2)
C16A—C12A—C12B—C14A	−26.5 (3)	C36A—C32A—C32B—C34A	−26.9 (3)
C22B—C21—C22—C23	0.6 (4)	C42B—C41—C42—C43	1.1 (4)
C21—C22—C23—C24	0.6 (4)	C41—C42—C43—C44	0.7 (4)
C22—C23—C24—C24A	−0.3 (4)	C42—C43—C44—C44A	−1.2 (4)
C23—C24—C24A—C22B	−1.2 (4)	C43—C44—C44A—C42B	0.0 (4)
C23—C24—C24A—C25	175.9 (2)	C43—C44—C44A—C45	178.8 (3)
C24—C24A—C25—C26	−138.0 (2)	C44—C44A—C45—C46	−138.5 (3)
C22B—C24A—C25—C26	39.2 (3)	C42B—C44A—C45—C46	40.3 (3)
C24A—C25—C26—C26A	−58.5 (3)	C44A—C45—C46—C46A	−57.9 (3)
C25—C26—C26A—N27	−139.5 (2)	C45—C46—C46A—N47	−141.9 (2)
C25—C26—C26A—C22A	38.8 (3)	C45—C46—C46A—C42A	37.2 (3)
C22A—C26A—N27—C27A	0.6 (4)	C42A—C46A—N47—C47A	−2.5 (4)
C26—C26A—N27—C27A	178.8 (2)	C46—C46A—N47—C47A	176.5 (2)
C26A—N27—C27A—N28	−177.6 (2)	C46A—N47—C47A—N48	−176.7 (2)
C26A—N27—C27A—C21A	−1.3 (4)	C46A—N47—C47A—C41A	−1.0 (4)
N27—C27A—N28—N29	176.1 (2)	N47—C47A—N48—N49	173.9 (2)
C21A—C27A—N28—N29	−0.9 (3)	C41A—C47A—N48—N49	−2.5 (3)
N27—C27A—N28—C281	0.1 (4)	N47—C47A—N48—C481	−8.3 (4)
C21A—C27A—N28—C281	−176.9 (2)	C41A—C47A—N48—C481	175.2 (2)
C27A—N28—C281—C286	−18.9 (4)	C47A—N48—C481—C486	9.2 (4)
N29—N28—C281—C286	165.4 (2)	N49—N48—C481—C486	−173.2 (2)
C27A—N28—C281—C282	162.6 (3)	C47A—N48—C481—C482	−171.3 (2)
N29—N28—C281—C282	−13.1 (3)	N49—N48—C481—C482	6.3 (3)
C286—C281—C282—C283	−0.8 (4)	C486—C481—C482—C483	0.7 (4)
N28—C281—C282—C283	177.7 (2)	N48—C481—C482—C483	−178.8 (3)
C281—C282—C283—C284	0.3 (4)	C481—C482—C483—C484	−1.0 (5)
C282—C283—C284—C285	0.3 (4)	C482—C483—C484—C485	0.6 (5)
C283—C284—C285—C286	−0.5 (4)	C483—C484—C485—C486	0.1 (5)
C282—C281—C286—C285	0.6 (4)	C482—C481—C486—C485	0.0 (4)
N28—C281—C286—C285	−177.8 (2)	N48—C481—C486—C485	179.5 (2)
C284—C285—C286—C281	0.0 (4)	C484—C485—C486—C481	−0.4 (4)
C27A—N28—N29—C210	0.9 (3)	C47A—N48—N49—C410	1.8 (3)
C281—N28—N29—C210	177.4 (2)	C481—N48—N49—C410	−176.2 (2)
N28—N29—C210—C21A	−0.5 (3)	N48—N49—C410—C41A	−0.4 (3)
N28—N29—C210—C211	179.4 (2)	N48—N49—C410—C411	179.1 (2)
N27—C27A—C21A—C220	−0.2 (4)	N47—C47A—C41A—C420	2.9 (4)
N28—C27A—C21A—C220	176.7 (2)	N48—C47A—C41A—C420	179.4 (2)
N27—C27A—C21A—C210	−176.4 (2)	N47—C47A—C41A—C410	−174.3 (2)
N28—C27A—C21A—C210	0.5 (3)	N48—C47A—C41A—C410	2.2 (3)
N29—C210—C21A—C27A	0.0 (3)	N49—C410—C41A—C47A	−1.1 (3)
C211—C210—C21A—C27A	−179.9 (3)	C411—C410—C41A—C47A	179.4 (3)
N29—C210—C21A—C220	−175.0 (3)	N49—C410—C41A—C420	−177.5 (3)
C211—C210—C21A—C220	5.1 (5)	C411—C410—C41A—C420	3.0 (5)
C27A—C21A—C220—C22A	2.4 (3)	C47A—C41A—C420—C42A	−1.4 (3)
C210—C21A—C220—C22A	176.9 (3)	C410—C41A—C420—C42A	174.7 (3)
C27A—C21A—C220—C221	−176.1 (2)	C47A—C41A—C420—C421	177.2 (2)
C210—C21A—C220—C221	−1.5 (4)	C410—C41A—C420—C421	−6.7 (4)
C22A—C220—C221—C226	118.8 (3)	C42A—C420—C421—C422	−70.2 (3)
C21A—C220—C221—C226	−62.8 (3)	C41A—C420—C421—C422	111.4 (3)
C22A—C220—C221—C222	−60.5 (3)	C42A—C420—C421—C426	111.5 (3)
C21A—C220—C221—C222	117.8 (3)	C41A—C420—C421—C426	−67.0 (3)
C226—C221—C222—C223	−0.3 (4)	C426—C421—C422—C423	0.9 (4)
C220—C221—C222—C223	179.0 (2)	C420—C421—C422—C423	−177.5 (2)
C221—C222—C223—C224	0.2 (4)	C421—C422—C423—C424	−0.5 (4)
C222—C223—C224—O224	−179.4 (2)	C422—C423—C424—O424	180.0 (2)
C222—C223—C224—C225	0.3 (4)	C422—C423—C424—C425	−0.6 (4)
C223—C224—O224—C227	6.0 (4)	C425—C424—O424—C427	178.4 (2)
C225—C224—O224—C227	−173.7 (2)	C423—C424—O424—C427	−2.2 (4)
O224—C224—C225—C226	178.9 (2)	O424—C424—C425—C426	−179.3 (2)
C223—C224—C225—C226	−0.8 (4)	C423—C424—C425—C426	1.2 (4)
C224—C225—C226—C221	0.7 (4)	C424—C425—C426—C421	−0.8 (4)
C222—C221—C226—C225	−0.1 (4)	C422—C421—C426—C425	−0.2 (4)
C220—C221—C226—C225	−179.5 (2)	C420—C421—C426—C425	178.2 (2)
C21A—C220—C22A—C26A	−3.0 (3)	C41A—C420—C42A—C46A	−1.7 (3)
C221—C220—C22A—C26A	175.4 (2)	C421—C420—C42A—C46A	179.9 (2)
C21A—C220—C22A—C22B	177.0 (2)	C41A—C420—C42A—C42B	178.8 (2)
C221—C220—C22A—C22B	−4.6 (4)	C421—C420—C42A—C42B	0.3 (4)
N27—C26A—C22A—C220	1.6 (4)	N47—C46A—C42A—C420	3.9 (4)
C26—C26A—C22A—C220	−176.5 (2)	C46—C46A—C42A—C420	−175.1 (2)
N27—C26A—C22A—C22B	−178.4 (2)	N47—C46A—C42A—C42B	−176.5 (2)
C26—C26A—C22A—C22B	3.4 (3)	C46—C46A—C42A—C42B	4.5 (3)
C22—C21—C22B—C24A	−2.1 (4)	C42—C41—C42B—C44A	−2.2 (4)
C22—C21—C22B—C22A	−180.0 (2)	C42—C41—C42B—C42A	179.2 (2)
C24—C24A—C22B—C21	2.3 (3)	C44—C44A—C42B—C41	1.7 (4)
C25—C24A—C22B—C21	−174.9 (2)	C45—C44A—C42B—C41	−177.1 (2)
C24—C24A—C22B—C22A	−179.7 (2)	C44—C44A—C42B—C42A	−179.7 (2)
C25—C24A—C22B—C22A	3.1 (3)	C45—C44A—C42B—C42A	1.5 (3)
C220—C22A—C22B—C21	−28.1 (4)	C420—C42A—C42B—C41	−27.4 (4)
C26A—C22A—C22B—C21	151.9 (2)	C46A—C42A—C42B—C41	153.1 (2)
C220—C22A—C22B—C24A	153.9 (2)	C420—C42A—C42B—C44A	154.1 (2)
C26A—C22A—C22B—C24A	−26.0 (3)	C46A—C42A—C42B—C44A	−25.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···N39	0.95	2.60	3.504 (3)	159
C326—H326···N47	0.95	2.59	3.526 (3)	168
C122—H122···Cg11	0.95	2.77	3.542 (3)	139
C222—H222···Cg12^i	0.95	2.77	3.568 (3)	142
C225—H225···Cg8^ii	0.95	2.76	3.628 (3)	152
C322—H322···Cg7^iii	0.95	2.77	3.483 (3)	132
C422—H422···Cg9	0.95	2.83	3.693 (3)	152

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2.

(XIV) 11-(3,4,5-trimethoxyphenyl)-10-methyl-8-phenyl-6,8- dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline

Crystal data

C30H27N3O3	F(000) = 1008
Mr = 477.55	Dx = 1.309 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5103 reflections
a = 10.4716 (9) Å	θ = 2.0–27.5°
b = 20.0027 (18) Å	µ = 0.09 mm^−1
c = 12.1529 (9) Å	T = 120 K
β = 107.818 (4)°	Plate, colourless
V = 2423.4 (4) Å^3	0.60 × 0.30 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2720 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.199
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
ϕ & ω scans	h = −13→13
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −25→25
Tmin = 0.963, Tmax = 0.998	l = −13→15
20344 measured 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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0625P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2720 reflections	Δρmax = 0.45 e Å^−3
329 parameters	Δρmin = −0.55 e Å^−3
2 restraints	Absolute structure: Friedel pairs merged
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
C1	0.3263 (5)	0.4933 (3)	0.5653 (5)	0.0304 (14)
C2	0.2303 (6)	0.4752 (3)	0.6162 (5)	0.0350 (14)
C3	0.1556 (6)	0.4177 (3)	0.5833 (5)	0.0378 (15)
C4	0.1805 (6)	0.3765 (3)	0.5016 (5)	0.0359 (15)
C4A	0.2751 (6)	0.3935 (3)	0.4474 (5)	0.0301 (13)
C5	0.3078 (6)	0.3481 (3)	0.3605 (5)	0.0342 (14)
C6	0.4592 (6)	0.3486 (3)	0.3795 (6)	0.0333 (14)
C6A	0.5020 (5)	0.4194 (3)	0.3676 (5)	0.0259 (13)
N7	0.5952 (4)	0.4266 (2)	0.3142 (4)	0.0262 (10)
C7A	0.6217 (5)	0.4911 (3)	0.2956 (5)	0.0254 (12)
N8	0.7079 (5)	0.5120 (2)	0.2383 (4)	0.0281 (11)
C81	0.7957 (5)	0.4746 (3)	0.1944 (5)	0.0270 (13)
C82	0.8051 (6)	0.4881 (3)	0.0857 (5)	0.0328 (14)
C83	0.8892 (6)	0.4505 (3)	0.0423 (6)	0.0363 (15)
C84	0.9624 (6)	0.3979 (3)	0.1052 (6)	0.0388 (16)
C85	0.9541 (6)	0.3852 (3)	0.2137 (5)	0.0354 (14)
C86	0.8713 (5)	0.4233 (3)	0.2602 (5)	0.0294 (13)
N9	0.6988 (5)	0.5813 (2)	0.2232 (4)	0.0307 (12)
C10	0.6125 (6)	0.6029 (3)	0.2741 (5)	0.0276 (13)
C101	0.5771 (7)	0.6761 (3)	0.2662 (6)	0.0420 (16)
C10A	0.5613 (5)	0.5479 (3)	0.3251 (5)	0.0237 (12)
C11	0.4722 (5)	0.5394 (3)	0.3887 (5)	0.0262 (13)
C111	0.4177 (5)	0.5994 (3)	0.4335 (5)	0.0258 (12)
C112	0.2810 (5)	0.6152 (3)	0.3975 (5)	0.0256 (13)
C113	0.2364 (5)	0.6698 (3)	0.4464 (5)	0.0264 (13)
O13	0.1052 (3)	0.68897 (19)	0.4203 (3)	0.0302 (9)
C13	0.0082 (6)	0.6530 (3)	0.3327 (5)	0.0338 (14)
C114	0.3277 (5)	0.7093 (3)	0.5287 (5)	0.0234 (12)
O14	0.2818 (4)	0.76181 (18)	0.5785 (3)	0.0303 (9)
C14	0.2968 (6)	0.8242 (3)	0.5245 (5)	0.0317 (14)
C115	0.4630 (5)	0.6951 (3)	0.5602 (5)	0.0272 (13)
O15	0.5445 (4)	0.73834 (18)	0.6382 (3)	0.0321 (9)
C15	0.6852 (5)	0.7236 (3)	0.6786 (5)	0.0325 (14)
C116	0.5102 (5)	0.6400 (3)	0.5138 (5)	0.0260 (12)
C12A	0.4414 (5)	0.4727 (3)	0.4124 (5)	0.0267 (13)
C12B	0.3464 (5)	0.4536 (3)	0.4757 (5)	0.0269 (13)
H1	0.3788	0.5324	0.5904	0.036*
H2	0.2154	0.5027	0.6748	0.042*
H3	0.0875	0.4066	0.6169	0.045*
H4	0.1322	0.3358	0.4819	0.043*
H5A	0.2599	0.3635	0.2811	0.041*
H5B	0.2779	0.3020	0.3693	0.041*
H6A	0.5072	0.3313	0.4575	0.040*
H6B	0.4809	0.3196	0.3217	0.040*
H82	0.7537	0.5233	0.0409	0.039*
H83	0.8970	0.4608	−0.0317	0.044*
H84	1.0175	0.3711	0.0736	0.047*
H85	1.0056	0.3499	0.2580	0.042*
H86	0.8667	0.4143	0.3357	0.035*
H10A	0.6100	0.6963	0.3432	0.050*
H10B	0.4795	0.6812	0.2362	0.050*
H10C	0.6189	0.6983	0.2141	0.050*
H112	0.2193	0.5889	0.3403	0.031*
H13A	0.0273	0.6579	0.2591	0.041*
H13B	−0.0815	0.6706	0.3249	0.041*
H13C	0.0118	0.6055	0.3537	0.041*
H14A	0.3912	0.8306	0.5294	0.038*
H14B	0.2676	0.8611	0.5642	0.038*
H14C	0.2419	0.8234	0.4432	0.038*
H15A	0.6991	0.6802	0.7180	0.039*
H15B	0.7320	0.7585	0.7325	0.039*
H15C	0.7206	0.7220	0.6127	0.039*
H116	0.6033	0.6301	0.5363	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.021 (3)	0.037 (3)	0.027 (3)	0.002 (3)	−0.003 (3)	0.003 (3)
C2	0.027 (3)	0.047 (4)	0.030 (3)	0.003 (3)	0.007 (3)	0.002 (3)
C3	0.029 (3)	0.048 (4)	0.037 (4)	−0.003 (3)	0.010 (3)	0.007 (3)
C4	0.026 (3)	0.037 (3)	0.041 (4)	−0.007 (3)	0.004 (3)	0.007 (3)
C4A	0.027 (3)	0.032 (3)	0.030 (3)	−0.003 (3)	0.006 (3)	0.002 (3)
C5	0.029 (3)	0.031 (3)	0.043 (4)	−0.005 (3)	0.012 (3)	0.000 (3)
C6	0.029 (3)	0.024 (3)	0.049 (4)	−0.003 (2)	0.015 (3)	−0.001 (3)
C6A	0.022 (3)	0.023 (3)	0.029 (3)	0.003 (2)	0.003 (3)	0.002 (2)
N7	0.022 (2)	0.021 (2)	0.034 (3)	−0.0006 (19)	0.007 (2)	−0.003 (2)
C7A	0.020 (3)	0.030 (3)	0.025 (3)	0.000 (3)	0.006 (2)	−0.001 (3)
N8	0.033 (3)	0.018 (2)	0.035 (3)	0.001 (2)	0.014 (2)	−0.001 (2)
C81	0.020 (3)	0.027 (3)	0.032 (4)	−0.005 (2)	0.004 (3)	−0.001 (3)
C82	0.030 (3)	0.032 (3)	0.035 (4)	0.002 (3)	0.007 (3)	0.004 (3)
C83	0.031 (3)	0.047 (4)	0.035 (3)	−0.003 (3)	0.014 (3)	−0.001 (3)
C84	0.030 (3)	0.046 (4)	0.042 (4)	0.010 (3)	0.015 (3)	−0.008 (3)
C85	0.027 (3)	0.042 (4)	0.035 (4)	0.004 (3)	0.006 (3)	0.006 (3)
C86	0.026 (3)	0.035 (3)	0.029 (3)	0.002 (3)	0.009 (3)	0.003 (3)
N9	0.030 (3)	0.031 (3)	0.031 (3)	−0.001 (2)	0.009 (2)	0.002 (2)
C10	0.030 (3)	0.027 (3)	0.027 (3)	0.002 (3)	0.010 (3)	0.001 (3)
C101	0.051 (4)	0.032 (4)	0.050 (4)	0.000 (3)	0.026 (3)	0.001 (3)
C10A	0.024 (3)	0.023 (3)	0.022 (3)	0.000 (2)	0.005 (2)	−0.003 (2)
C11	0.022 (3)	0.028 (3)	0.026 (3)	−0.004 (2)	0.003 (2)	−0.005 (3)
C111	0.027 (3)	0.022 (3)	0.029 (3)	0.002 (2)	0.009 (3)	0.004 (2)
C112	0.023 (3)	0.023 (3)	0.027 (3)	−0.004 (2)	0.002 (3)	0.001 (2)
C113	0.027 (3)	0.026 (3)	0.028 (3)	0.004 (2)	0.011 (3)	0.006 (3)
O13	0.022 (2)	0.031 (2)	0.035 (2)	0.0009 (17)	0.0045 (17)	−0.0029 (18)
C13	0.022 (3)	0.041 (4)	0.037 (3)	−0.004 (3)	0.007 (3)	−0.005 (3)
C114	0.028 (3)	0.023 (3)	0.020 (3)	0.002 (2)	0.008 (2)	0.000 (2)
O14	0.036 (2)	0.028 (2)	0.032 (2)	0.0027 (18)	0.0170 (18)	−0.0018 (18)
C14	0.032 (3)	0.024 (3)	0.040 (4)	0.003 (3)	0.012 (3)	−0.004 (3)
C115	0.025 (3)	0.025 (3)	0.030 (3)	0.003 (2)	0.007 (3)	0.000 (2)
O15	0.028 (2)	0.029 (2)	0.034 (2)	0.0010 (18)	0.0006 (18)	−0.0062 (19)
C15	0.026 (3)	0.036 (3)	0.032 (3)	0.002 (3)	0.003 (3)	−0.007 (3)
C116	0.021 (3)	0.026 (3)	0.032 (3)	0.002 (2)	0.010 (2)	0.003 (2)
C12A	0.017 (3)	0.030 (3)	0.030 (3)	−0.001 (2)	0.003 (2)	0.000 (3)
C12B	0.020 (3)	0.027 (3)	0.032 (3)	0.002 (2)	0.005 (2)	0.005 (3)

Geometric parameters (Å, º)

C1—C2	1.380 (8)	C86—H86	0.95
C1—C12B	1.415 (8)	N9—C10	1.313 (7)
C1—H1	0.95	C10—C10A	1.444 (8)
C2—C3	1.380 (9)	C10—C101	1.506 (8)
C2—H2	0.95	C101—H10A	0.98
C3—C4	1.375 (9)	C101—H10B	0.98
C3—H3	0.95	C101—H10C	0.98
C4—C4A	1.390 (8)	C10A—C11	1.392 (8)
C4—H4	0.95	C11—C12A	1.423 (7)
C4A—C12B	1.401 (8)	C11—C111	1.502 (8)
C4A—C5	1.510 (8)	C111—C112	1.399 (7)
C5—C6	1.530 (8)	C111—C116	1.404 (8)
C5—H5A	0.99	C112—C113	1.390 (7)
C5—H5B	0.99	C112—H112	0.95
C6—C6A	1.506 (8)	C113—O13	1.367 (6)
C6—H6A	0.99	C113—C114	1.397 (7)
C6—H6B	0.99	O13—C13	1.422 (7)
C6A—N7	1.334 (7)	C13—H13A	0.98
C6A—C12A	1.430 (7)	C13—H13B	0.98
N7—C7A	1.352 (7)	C13—H13C	0.98
C7A—N8	1.363 (7)	C114—O14	1.371 (6)
C7A—C10A	1.400 (8)	C114—C115	1.380 (7)
N8—N9	1.398 (6)	O14—C14	1.441 (7)
N8—C81	1.411 (7)	C14—H14A	0.98
C81—C82	1.381 (8)	C14—H14B	0.98
C81—C86	1.389 (8)	C14—H14C	0.98
C82—C83	1.380 (9)	C115—O15	1.371 (6)
C82—H82	0.95	C115—C116	1.395 (8)
C83—C84	1.386 (9)	O15—C15	1.434 (7)
C83—H83	0.95	C15—H15A	0.98
C84—C85	1.372 (9)	C15—H15B	0.98
C84—H84	0.95	C15—H15C	0.98
C85—C86	1.398 (8)	C116—H116	0.95
C85—H85	0.95	C12A—C12B	1.481 (8)
C2—C1—C12B	119.8 (5)	C10A—C10—C101	130.6 (5)
C2—C1—H1	120.1	C10—C101—H10A	109.5
C12B—C1—H1	120.1	C10—C101—H10B	109.5
C1—C2—C3	121.1 (6)	H10A—C101—H10B	109.5
C1—C2—H2	119.5	C10—C101—H10C	109.5
C3—C2—H2	119.5	H10A—C101—H10C	109.5
C4—C3—C2	119.5 (6)	H10B—C101—H10C	109.5
C4—C3—H3	120.3	C11—C10A—C7A	118.3 (5)
C2—C3—H3	120.3	C11—C10A—C10	137.1 (5)
C3—C4—C4A	121.1 (6)	C7A—C10A—C10	104.6 (5)
C3—C4—H4	119.5	C10A—C11—C12A	117.4 (5)
C4A—C4—H4	119.5	C10A—C11—C111	119.8 (5)
C4—C4A—C12B	119.8 (5)	C12A—C11—C111	122.7 (5)
C4—C4A—C5	122.1 (5)	C112—C111—C116	120.6 (5)
C12B—C4A—C5	118.1 (5)	C112—C111—C11	122.3 (5)
C4A—C5—C6	109.7 (5)	C116—C111—C11	117.2 (5)
C4A—C5—H5A	109.7	C113—C112—C111	119.3 (5)
C6—C5—H5A	109.7	C113—C112—H112	120.4
C4A—C5—H5B	109.7	C111—C112—H112	120.4
C6—C5—H5B	109.7	O13—C113—C112	124.5 (5)
H5A—C5—H5B	108.2	O13—C113—C114	115.2 (4)
C6A—C6—C5	108.5 (5)	C112—C113—C114	120.3 (5)
C6A—C6—H6A	110.0	C113—O13—C13	118.0 (4)
C5—C6—H6A	110.0	O13—C13—H13A	109.5
C6A—C6—H6B	110.0	O13—C13—H13B	109.5
C5—C6—H6B	110.0	H13A—C13—H13B	109.5
H6A—C6—H6B	108.4	O13—C13—H13C	109.5
N7—C6A—C12A	125.5 (5)	H13A—C13—H13C	109.5
N7—C6A—C6	115.6 (5)	H13B—C13—H13C	109.5
C12A—C6A—C6	118.9 (5)	O14—C114—C115	120.3 (5)
C6A—N7—C7A	113.8 (5)	O14—C114—C113	119.6 (5)
N7—C7A—N8	125.5 (5)	C115—C114—C113	120.1 (5)
N7—C7A—C10A	126.8 (5)	C114—O14—C14	111.1 (4)
N8—C7A—C10A	107.6 (5)	O14—C14—H14A	109.5
C7A—N8—N9	110.0 (4)	O14—C14—H14B	109.5
C7A—N8—C81	129.8 (4)	H14A—C14—H14B	109.5
N9—N8—C81	120.1 (4)	O14—C14—H14C	109.5
C82—C81—C86	120.0 (5)	H14A—C14—H14C	109.5
C82—C81—N8	120.2 (5)	H14B—C14—H14C	109.5
C86—C81—N8	119.8 (5)	O15—C115—C114	115.5 (5)
C83—C82—C81	120.0 (6)	O15—C115—C116	123.8 (5)
C83—C82—H82	120.0	C114—C115—C116	120.7 (5)
C81—C82—H82	120.0	C115—O15—C15	117.6 (4)
C82—C83—C84	120.9 (6)	O15—C15—H15A	109.5
C82—C83—H83	119.6	O15—C15—H15B	109.5
C84—C83—H83	119.6	H15A—C15—H15B	109.5
C85—C84—C83	118.9 (6)	O15—C15—H15C	109.5
C85—C84—H84	120.5	H15A—C15—H15C	109.5
C83—C84—H84	120.5	H15B—C15—H15C	109.5
C84—C85—C86	121.2 (6)	C115—C116—C111	118.9 (5)
C84—C85—H85	119.4	C115—C116—H116	120.5
C86—C85—H85	119.4	C111—C116—H116	120.5
C81—C86—C85	119.0 (5)	C11—C12A—C6A	117.8 (5)
C81—C86—H86	120.5	C11—C12A—C12B	125.2 (5)
C85—C86—H86	120.5	C6A—C12A—C12B	117.0 (5)
C10—N9—N8	107.0 (4)	C4A—C12B—C1	118.5 (5)
N9—C10—C10A	110.6 (5)	C4A—C12B—C12A	119.0 (5)
N9—C10—C101	118.7 (5)	C1—C12B—C12A	122.5 (5)
C12B—C1—C2—C3	1.8 (9)	C10—C10A—C11—C111	−8.6 (10)
C1—C2—C3—C4	2.4 (9)	C10A—C11—C111—C112	116.6 (6)
C2—C3—C4—C4A	−3.2 (9)	C12A—C11—C111—C112	−66.2 (7)
C3—C4—C4A—C12B	−0.2 (9)	C10A—C11—C111—C116	−63.1 (7)
C3—C4—C4A—C5	177.8 (6)	C12A—C11—C111—C116	114.1 (6)
C4—C4A—C5—C6	−139.5 (6)	C116—C111—C112—C113	−3.2 (8)
C12B—C4A—C5—C6	38.5 (7)	C11—C111—C112—C113	177.1 (5)
C4A—C5—C6—C6A	−58.4 (6)	C111—C112—C113—O13	−178.3 (5)
C5—C6—C6A—N7	−141.3 (5)	C111—C112—C113—C114	1.5 (7)
C5—C6—C6A—C12A	38.4 (7)	C112—C113—O13—C13	−3.5 (7)
C12A—C6A—N7—C7A	−5.6 (7)	C114—C113—O13—C13	176.7 (5)
C6—C6A—N7—C7A	174.1 (5)	O13—C113—C114—O14	1.7 (7)
C6A—N7—C7A—N8	−176.8 (5)	C112—C113—C114—O14	−178.2 (5)
C6A—N7—C7A—C10A	−0.8 (8)	O13—C113—C114—C115	−178.9 (5)
N7—C7A—N8—N9	172.9 (5)	C112—C113—C114—C115	1.2 (7)
C10A—C7A—N8—N9	−3.8 (6)	C115—C114—O14—C14	81.2 (6)
N7—C7A—N8—C81	−5.8 (9)	C113—C114—O14—C14	−99.4 (5)
C10A—C7A—N8—C81	177.5 (5)	O14—C114—C115—O15	−2.9 (7)
C7A—N8—C81—C82	136.1 (6)	C113—C114—C115—O15	177.7 (5)
N9—N8—C81—C82	−42.5 (7)	O14—C114—C115—C116	177.1 (5)
C7A—N8—C81—C86	−42.9 (8)	C113—C114—C115—C116	−2.3 (8)
N9—N8—C81—C86	138.6 (5)	C114—C115—O15—C15	176.6 (5)
C86—C81—C82—C83	0.3 (8)	C116—C115—O15—C15	−3.5 (7)
N8—C81—C82—C83	−178.7 (5)	O15—C115—C116—C111	−179.3 (5)
C81—C82—C83—C84	1.6 (9)	C114—C115—C116—C111	0.6 (8)
C82—C83—C84—C85	−2.4 (10)	C112—C111—C116—C115	2.1 (8)
C83—C84—C85—C86	1.4 (9)	C11—C111—C116—C115	−178.1 (5)
C82—C81—C86—C85	−1.3 (8)	C10A—C11—C12A—C6A	−1.1 (7)
N8—C81—C86—C85	177.7 (5)	C111—C11—C12A—C6A	−178.4 (5)
C84—C85—C86—C81	0.4 (9)	C10A—C11—C12A—C12B	−178.2 (5)
C7A—N8—N9—C10	2.3 (6)	C111—C11—C12A—C12B	4.5 (8)
C81—N8—N9—C10	−178.8 (5)	N7—C6A—C12A—C11	6.7 (8)
N8—N9—C10—C10A	0.0 (6)	C6—C6A—C12A—C11	−173.0 (5)
N8—N9—C10—C101	−176.9 (5)	N7—C6A—C12A—C12B	−176.0 (5)
N7—C7A—C10A—C11	5.8 (8)	C6—C6A—C12A—C12B	4.3 (7)
N8—C7A—C10A—C11	−177.6 (5)	C4—C4A—C12B—C1	4.4 (8)
N7—C7A—C10A—C10	−173.1 (6)	C5—C4A—C12B—C1	−173.7 (5)
N8—C7A—C10A—C10	3.6 (6)	C4—C4A—C12B—C12A	−176.7 (5)
N9—C10—C10A—C11	179.2 (6)	C5—C4A—C12B—C12A	5.2 (8)
C101—C10—C10A—C11	−4.4 (11)	C2—C1—C12B—C4A	−5.2 (8)
N9—C10—C10A—C7A	−2.2 (6)	C2—C1—C12B—C12A	175.9 (5)
C101—C10—C10A—C7A	174.2 (6)	C11—C12A—C12B—C4A	148.9 (5)
C7A—C10A—C11—C12A	−4.4 (7)	C6A—C12A—C12B—C4A	−28.2 (7)
C10—C10A—C11—C12A	174.0 (6)	C11—C12A—C12B—C1	−32.2 (8)
C7A—C10A—C11—C111	173.0 (5)	C6A—C12A—C12B—C1	150.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C82—H82···Cg13^i	0.95	2.73	3.472 (6)	130

Symmetry code: (i) x+1, −y, z−1/2.

(XV) 8-methyl-7-(4-pyridinyl)-10-phenyl-10H- benzo[h]pyrazolo[3,4-b]quinoline

Crystal data

C26H18N4	F(000) = 808
Mr = 386.44	Dx = 1.346 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4372 reflections
a = 11.3560 (3) Å	θ = 2.9–27.5°
b = 17.3507 (5) Å	µ = 0.08 mm^−1
c = 9.7577 (2) Å	T = 120 K
β = 97.262 (2)°	Lath, colourless
V = 1907.18 (8) Å^3	0.50 × 0.24 × 0.10 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	4372 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ & ω scans	h = −14→14
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −22→21
Tmin = 0.971, Tmax = 0.992	l = −12→12
26391 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0831P)^2] where P = (Fo^2 + 2Fc^2)/3
4372 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
C1	0.21448 (15)	0.35074 (10)	0.50320 (16)	0.0270 (4)
C2	0.15537 (16)	0.29981 (10)	0.57854 (17)	0.0300 (4)
C3	0.21775 (16)	0.24243 (10)	0.65708 (17)	0.0319 (4)
C4	0.33858 (16)	0.23696 (11)	0.65857 (18)	0.0364 (5)
C4A	0.40076 (15)	0.28765 (10)	0.58222 (16)	0.0284 (4)
C5	0.52758 (16)	0.28100 (11)	0.5806 (2)	0.0398 (5)
C6	0.58638 (16)	0.32743 (11)	0.50234 (19)	0.0373 (5)
C6A	0.52606 (14)	0.38826 (9)	0.41853 (15)	0.0238 (4)
C7	0.58593 (14)	0.43595 (9)	0.33297 (15)	0.0230 (4)
C71	0.71477 (14)	0.42529 (9)	0.32303 (16)	0.0235 (4)
C72	0.80096 (15)	0.43672 (10)	0.43597 (17)	0.0280 (4)
C73	0.91823 (15)	0.42338 (10)	0.42185 (17)	0.0284 (4)
N74	0.95701 (12)	0.40019 (8)	0.30454 (14)	0.0305 (4)
C75	0.87328 (15)	0.38993 (10)	0.19608 (17)	0.0306 (4)
C76	0.75347 (15)	0.40106 (10)	0.20057 (16)	0.0268 (4)
C7A	0.51852 (14)	0.49169 (9)	0.25525 (15)	0.0224 (4)
C8	0.53921 (15)	0.55383 (9)	0.16384 (16)	0.0260 (4)
C81	0.65178 (15)	0.58037 (11)	0.11540 (18)	0.0323 (4)
N9	0.43940 (12)	0.59074 (8)	0.12348 (13)	0.0278 (4)
N10	0.35014 (12)	0.55494 (8)	0.18465 (13)	0.0250 (3)
C101	0.23473 (15)	0.58816 (10)	0.17145 (16)	0.0252 (4)
C102	0.22343 (16)	0.66740 (10)	0.15336 (17)	0.0337 (4)
C103	0.11157 (18)	0.70048 (11)	0.13938 (18)	0.0404 (5)
C104	0.01195 (18)	0.65562 (12)	0.14412 (17)	0.0393 (5)
C105	0.02419 (16)	0.57690 (12)	0.16256 (18)	0.0374 (5)
C106	0.13528 (15)	0.54244 (10)	0.17547 (17)	0.0297 (4)
C10A	0.39630 (14)	0.49528 (9)	0.26704 (15)	0.0223 (4)
N11	0.33552 (12)	0.45111 (7)	0.34522 (13)	0.0223 (3)
C11A	0.40127 (14)	0.39777 (9)	0.42079 (15)	0.0211 (4)
C11B	0.33774 (14)	0.34580 (9)	0.50358 (15)	0.0223 (4)
H1	0.1711	0.3897	0.4503	0.032*
H2	0.0718	0.3038	0.5770	0.036*
H3	0.1770	0.2074	0.7092	0.038*
H4	0.3809	0.1979	0.7126	0.044*
H5	0.5704	0.2429	0.6363	0.048*
H6	0.6693	0.3203	0.5018	0.045*
H72	0.7790	0.4536	0.5218	0.034*
H73	0.9754	0.4311	0.5005	0.034*
H75	0.8980	0.3740	0.1110	0.037*
H76	0.6980	0.3922	0.1207	0.032*
H81A	0.6802	0.5410	0.0555	0.048*
H81B	0.7118	0.5890	0.1953	0.048*
H81C	0.6374	0.6286	0.0636	0.048*
H102	0.2918	0.6986	0.1506	0.040*
H103	0.1034	0.7546	0.1264	0.049*
H104	−0.0645	0.6786	0.1348	0.047*
H105	−0.0444	0.5460	0.1664	0.045*
H106	0.1430	0.4882	0.1869	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0276 (10)	0.0283 (9)	0.0246 (8)	0.0035 (7)	0.0020 (7)	0.0017 (7)
C2	0.0284 (10)	0.0343 (10)	0.0278 (9)	−0.0006 (8)	0.0051 (7)	0.0001 (8)
C3	0.0369 (11)	0.0327 (10)	0.0270 (9)	−0.0021 (8)	0.0073 (8)	0.0048 (8)
C4	0.0393 (12)	0.0350 (11)	0.0349 (10)	0.0065 (9)	0.0047 (8)	0.0132 (8)
C4A	0.0322 (10)	0.0270 (9)	0.0260 (9)	0.0035 (8)	0.0032 (7)	0.0017 (7)
C5	0.0306 (11)	0.0411 (11)	0.0475 (11)	0.0114 (9)	0.0032 (9)	0.0193 (9)
C6	0.0255 (10)	0.0453 (12)	0.0416 (10)	0.0114 (9)	0.0057 (8)	0.0142 (9)
C6A	0.0233 (9)	0.0251 (9)	0.0229 (8)	0.0047 (7)	0.0024 (7)	−0.0003 (7)
C7	0.0237 (9)	0.0264 (9)	0.0185 (8)	0.0025 (7)	0.0014 (6)	−0.0047 (7)
C71	0.0222 (9)	0.0233 (9)	0.0248 (8)	0.0016 (7)	0.0021 (7)	0.0029 (7)
C72	0.0295 (10)	0.0293 (10)	0.0245 (9)	0.0027 (8)	0.0008 (7)	−0.0012 (7)
C73	0.0249 (10)	0.0278 (9)	0.0310 (9)	0.0009 (7)	−0.0027 (7)	−0.0002 (7)
N74	0.0253 (8)	0.0334 (9)	0.0329 (8)	0.0006 (6)	0.0046 (6)	0.0038 (6)
C75	0.0283 (11)	0.0378 (10)	0.0262 (9)	0.0022 (8)	0.0062 (7)	0.0010 (8)
C76	0.0244 (10)	0.0323 (10)	0.0232 (8)	0.0021 (7)	0.0007 (7)	0.0003 (7)
C7A	0.0229 (9)	0.0244 (9)	0.0195 (8)	0.0000 (7)	0.0010 (6)	−0.0028 (7)
C8	0.0260 (10)	0.0271 (9)	0.0242 (8)	−0.0001 (7)	0.0010 (7)	−0.0003 (7)
C81	0.0288 (10)	0.0353 (10)	0.0336 (10)	−0.0022 (8)	0.0066 (8)	0.0045 (8)
N9	0.0271 (8)	0.0287 (8)	0.0276 (8)	−0.0024 (6)	0.0039 (6)	0.0027 (6)
N10	0.0240 (8)	0.0247 (8)	0.0261 (7)	0.0022 (6)	0.0024 (6)	0.0057 (6)
C101	0.0258 (10)	0.0296 (10)	0.0194 (8)	0.0066 (7)	0.0004 (7)	0.0005 (7)
C102	0.0373 (11)	0.0276 (10)	0.0336 (9)	0.0040 (8)	−0.0055 (8)	−0.0017 (8)
C103	0.0510 (13)	0.0313 (11)	0.0364 (10)	0.0155 (10)	−0.0048 (9)	−0.0038 (8)
C104	0.0381 (12)	0.0539 (13)	0.0263 (9)	0.0233 (10)	0.0054 (8)	0.0063 (9)
C105	0.0280 (11)	0.0516 (12)	0.0339 (10)	0.0083 (9)	0.0084 (8)	0.0156 (9)
C106	0.0277 (10)	0.0315 (10)	0.0297 (9)	0.0057 (8)	0.0031 (7)	0.0093 (8)
C10A	0.0245 (9)	0.0236 (9)	0.0181 (8)	0.0021 (7)	0.0001 (6)	−0.0019 (7)
N11	0.0237 (8)	0.0222 (7)	0.0205 (7)	0.0021 (6)	0.0012 (6)	−0.0010 (6)
C11A	0.0244 (9)	0.0209 (8)	0.0173 (7)	0.0037 (7)	−0.0004 (6)	−0.0030 (6)
C11B	0.0268 (10)	0.0230 (9)	0.0170 (7)	0.0018 (7)	0.0019 (7)	−0.0046 (7)

Geometric parameters (Å, º)

C1—C2	1.377 (2)	C75—H75	0.95
C1—C11B	1.402 (2)	C76—H76	0.95
C1—H1	0.95	C7A—C10A	1.409 (2)
C2—C3	1.394 (2)	C7A—C8	1.437 (2)
C2—H2	0.95	C8—N9	1.318 (2)
C3—C4	1.374 (2)	C8—C81	1.491 (2)
C3—H3	0.95	C81—H81A	0.98
C4—C4A	1.400 (2)	C81—H81B	0.98
C4—H4	0.95	C81—H81C	0.98
C4A—C11B	1.407 (2)	N9—N10	1.3865 (18)
C4A—C5	1.447 (2)	N10—C10A	1.373 (2)
C5—C6	1.344 (2)	N10—C101	1.423 (2)
C5—H5	0.95	C101—C106	1.385 (2)
C6—C6A	1.453 (2)	C101—C102	1.390 (2)
C6—H6	0.95	C102—C103	1.385 (3)
C6A—C7	1.410 (2)	C102—H102	0.95
C6A—C11A	1.430 (2)	C103—C104	1.379 (3)
C7—C7A	1.396 (2)	C103—H103	0.95
C7—C71	1.490 (2)	C104—C105	1.382 (3)
C71—C76	1.389 (2)	C104—H104	0.95
C71—C72	1.393 (2)	C105—C106	1.387 (2)
C72—C73	1.376 (2)	C105—H105	0.95
C72—H72	0.95	C106—H106	0.95
C73—N74	1.339 (2)	C10A—N11	1.334 (2)
C73—H73	0.95	N11—C11A	1.349 (2)
N74—C75	1.342 (2)	C11A—C11B	1.461 (2)
C75—C76	1.380 (2)
C2—C1—C11B	120.88 (15)	C7—C7A—C8	137.32 (15)
C2—C1—H1	119.6	C10A—C7A—C8	104.92 (14)
C11B—C1—H1	119.6	N9—C8—C7A	110.37 (14)
C1—C2—C3	120.24 (16)	N9—C8—C81	119.65 (15)
C1—C2—H2	119.9	C7A—C8—C81	129.97 (15)
C3—C2—H2	119.9	C8—C81—H81A	109.5
C4—C3—C2	119.52 (16)	C8—C81—H81B	109.5
C4—C3—H3	120.2	H81A—C81—H81B	109.5
C2—C3—H3	120.2	C8—C81—H81C	109.5
C3—C4—C4A	121.42 (16)	H81A—C81—H81C	109.5
C3—C4—H4	119.3	H81B—C81—H81C	109.5
C4A—C4—H4	119.3	C8—N9—N10	107.56 (13)
C4—C4A—C11B	118.99 (16)	C10A—N10—N9	110.11 (13)
C4—C4A—C5	121.70 (16)	C10A—N10—C101	129.60 (14)
C11B—C4A—C5	119.31 (15)	N9—N10—C101	119.66 (13)
C6—C5—C4A	121.68 (16)	C106—C101—C102	120.51 (16)
C6—C5—H5	119.2	C106—C101—N10	120.70 (15)
C4A—C5—H5	119.2	C102—C101—N10	118.78 (15)
C5—C6—C6A	121.50 (17)	C103—C102—C101	119.42 (18)
C5—C6—H6	119.3	C103—C102—H102	120.3
C6A—C6—H6	119.3	C101—C102—H102	120.3
C7—C6A—C11A	119.65 (14)	C104—C103—C102	120.60 (18)
C7—C6A—C6	122.10 (15)	C104—C103—H103	119.7
C11A—C6A—C6	118.23 (15)	C102—C103—H103	119.7
C7A—C7—C6A	117.12 (15)	C103—C104—C105	119.52 (18)
C7A—C7—C71	121.74 (14)	C103—C104—H104	120.2
C6A—C7—C71	121.11 (14)	C105—C104—H104	120.2
C76—C71—C72	117.17 (15)	C104—C105—C106	120.86 (18)
C76—C71—C7	120.90 (14)	C104—C105—H105	119.6
C72—C71—C7	121.91 (14)	C106—C105—H105	119.6
C73—C72—C71	119.29 (15)	C101—C106—C105	119.08 (17)
C73—C72—H72	120.4	C101—C106—H106	120.5
C71—C72—H72	120.4	C105—C106—H106	120.5
N74—C73—C72	124.28 (15)	N11—C10A—N10	125.53 (15)
N74—C73—H73	117.9	N11—C10A—C7A	127.43 (14)
C72—C73—H73	117.9	N10—C10A—C7A	107.02 (14)
C73—N74—C75	115.91 (14)	C10A—N11—C11A	114.60 (14)
N74—C75—C76	124.01 (15)	N11—C11A—C6A	123.51 (14)
N74—C75—H75	118.0	N11—C11A—C11B	116.62 (14)
C76—C75—H75	118.0	C6A—C11A—C11B	119.81 (14)
C75—C76—C71	119.33 (15)	C1—C11B—C4A	118.95 (15)
C75—C76—H76	120.3	C1—C11B—C11A	121.57 (14)
C71—C76—H76	120.3	C4A—C11B—C11A	119.44 (15)
C7—C7A—C10A	117.68 (14)
C11B—C1—C2—C3	0.2 (2)	C10A—N10—C101—C106	−38.1 (2)
C1—C2—C3—C4	−0.1 (3)	N9—N10—C101—C106	151.94 (15)
C2—C3—C4—C4A	−0.3 (3)	C10A—N10—C101—C102	142.43 (17)
C3—C4—C4A—C11B	0.6 (3)	N9—N10—C101—C102	−27.6 (2)
C3—C4—C4A—C5	−178.43 (17)	C106—C101—C102—C103	0.0 (2)
C4—C4A—C5—C6	176.90 (18)	N10—C101—C102—C103	179.54 (15)
C11B—C4A—C5—C6	−2.2 (3)	C101—C102—C103—C104	0.4 (3)
C4A—C5—C6—C6A	1.9 (3)	C102—C103—C104—C105	−0.2 (3)
C5—C6—C6A—C7	−178.16 (18)	C103—C104—C105—C106	−0.4 (3)
C5—C6—C6A—C11A	−0.1 (3)	C102—C101—C106—C105	−0.6 (2)
C11A—C6A—C7—C7A	0.9 (2)	N10—C101—C106—C105	179.86 (14)
C6—C6A—C7—C7A	178.95 (15)	C104—C105—C106—C101	0.8 (3)
C11A—C6A—C7—C71	−177.14 (13)	N9—N10—C10A—N11	177.00 (14)
C6—C6A—C7—C71	0.9 (2)	C101—N10—C10A—N11	6.2 (3)
C7A—C7—C71—C76	−64.3 (2)	N9—N10—C10A—C7A	−1.51 (17)
C6A—C7—C71—C76	113.68 (17)	C101—N10—C10A—C7A	−172.26 (14)
C7A—C7—C71—C72	117.68 (18)	C7—C7A—C10A—N11	0.1 (2)
C6A—C7—C71—C72	−64.3 (2)	C8—C7A—C10A—N11	−177.24 (15)
C76—C71—C72—C73	−0.4 (2)	C7—C7A—C10A—N10	178.58 (13)
C7—C71—C72—C73	177.73 (15)	C8—C7A—C10A—N10	1.23 (16)
C71—C72—C73—N74	0.5 (3)	N10—C10A—N11—C11A	−177.85 (14)
C72—C73—N74—C75	0.0 (2)	C7A—C10A—N11—C11A	0.3 (2)
C73—N74—C75—C76	−0.7 (3)	C10A—N11—C11A—C6A	−0.2 (2)
N74—C75—C76—C71	0.8 (3)	C10A—N11—C11A—C11B	−177.45 (13)
C72—C71—C76—C75	−0.3 (2)	C7—C6A—C11A—N11	−0.5 (2)
C7—C71—C76—C75	−178.39 (15)	C6—C6A—C11A—N11	−178.58 (14)
C6A—C7—C7A—C10A	−0.8 (2)	C7—C6A—C11A—C11B	176.72 (14)
C71—C7—C7A—C10A	177.31 (13)	C6—C6A—C11A—C11B	−1.4 (2)
C6A—C7—C7A—C8	175.47 (17)	C2—C1—C11B—C4A	0.1 (2)
C71—C7—C7A—C8	−6.5 (3)	C2—C1—C11B—C11A	178.00 (15)
C7—C7A—C8—N9	−177.09 (17)	C4—C4A—C11B—C1	−0.6 (2)
C10A—C7A—C8—N9	−0.55 (17)	C5—C4A—C11B—C1	178.54 (15)
C7—C7A—C8—C81	1.6 (3)	C4—C4A—C11B—C11A	−178.46 (15)
C10A—C7A—C8—C81	178.14 (16)	C5—C4A—C11B—C11A	0.6 (2)
C7A—C8—N9—N10	−0.36 (18)	N11—C11A—C11B—C1	0.6 (2)
C81—C8—N9—N10	−179.20 (13)	C6A—C11A—C11B—C1	−176.77 (14)
C8—N9—N10—C10A	1.17 (17)	N11—C11A—C11B—C4A	178.49 (14)
C8—N9—N10—C101	172.98 (13)	C6A—C11A—C11B—C4A	1.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C72—H72···N11^i	0.95	2.56	3.404 (2)	149
C75—H75···Cg2^ii	0.95	2.60	3.463 (2)	151
C4—H4···Cg3^iii	0.95	2.84	3.771 (2)	165
C4—H4···Cg4^iii	0.95	2.92	3.700 (2)	140
C103—H103···Cg5^iv	0.95	2.87	3.749 (2)	154

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, −y−1/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2.