2-[3,5-Bis(4-meth-oxy-phen-yl)-4,5-di-hydro-1H-pyrazol-1-yl]-4,6-bis-(4-meth-oxy-phen-yl)pyrimidine.

In the title compound, C(35)H(32)N(4)O(4), the pyrazole ring forms a dihedral angle of 15.04 (8)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.95 (8) and 1.86 (7)° with its adjacent meth-oxy-substituted benzene rings, whereas the equivalent angles are 80.24 (9) and 11.55 (9)° for the pyrazole ring and its adjacent benzene rings. The crystal packing features π-π inter-actions, the centroid-centroid distance between the pyrimidine and methoxyphenyl rings being 3.604 (1) Å. The pyrazole ring is nearly planar, with a maximum deviation of 0.020 (3) Å for the -CH(2)- carbon.

Related literature

For biological importance of substituted pyrimidines, see: Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶); Samshuddin et al. (2011 ▶); Betz et al. (2012 ▶). For related literature on substituted pyrimidines and their derivatives, see: Calabresi et al. (1975 ▶); El-Hashash et al. (1993 ▶); Fun et al. (2012 ▶).

Experimental

Crystal data

C35H32N4O4

M = 572.65

Monoclinic,

a = 21.637 (2) Å

b = 5.9532 (4) Å

c = 24.749 (2) Å

β = 109.519 (10)°

V = 3004.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.887, T max = 1.000

12486 measured reflections

5824 independent reflections

3423 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.05

5824 reflections

393 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030516/bh2441sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030516/bh2441Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030516/bh2441Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C35H32N4O4	F(000) = 1208
Mr = 572.65	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Melting point: 502 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 21.637 (2) Å	Cell parameters from 4664 reflections
b = 5.9532 (4) Å	θ = 3.1–32.2°
c = 24.749 (2) Å	µ = 0.08 mm−1
β = 109.519 (10)°	T = 293 K
V = 3004.7 (5) Å3	Needle, white
Z = 4	0.3 × 0.2 × 0.2 mm

Agilent Xcalibur Sapphire3 diffractometer	5824 independent reflections
Radiation source: fine-focus sealed tube	3423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scan	h = −26→22
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.887, Tmax = 1.000	l = −30→29
12486 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0751P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5824 reflections	Δρmax = 0.16 e Å−3
393 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0036 (7)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.94094 (10)	0.2692 (3)	0.65771 (9)	0.0460 (5)
N2	0.97976 (8)	0.4493 (3)	0.66528 (7)	0.0468 (4)
C3	0.97863 (9)	0.5581 (3)	0.61747 (8)	0.0435 (5)
C4	0.93798 (10)	0.4855 (3)	0.56368 (9)	0.0501 (5)
H4	0.9372	0.5613	0.5306	0.060*
C5	0.89887 (9)	0.2986 (3)	0.56049 (8)	0.0443 (5)
N6	0.89964 (8)	0.1872 (3)	0.60806 (7)	0.0475 (4)
C7	1.02191 (9)	0.7565 (3)	0.62675 (8)	0.0440 (5)
C8	1.05920 (11)	0.8194 (4)	0.68218 (9)	0.0607 (6)
H8	1.0567	0.7329	0.7127	0.073*
C9	1.09970 (12)	1.0049 (4)	0.69371 (9)	0.0619 (6)
H9	1.1234	1.0428	0.7314	0.074*
C10	1.10489 (10)	1.1338 (3)	0.64922 (9)	0.0486 (5)
C11	1.06833 (11)	1.0755 (4)	0.59376 (9)	0.0590 (6)
H11	1.0710	1.1626	0.5634	0.071*
C12	1.02815 (10)	0.8910 (3)	0.58281 (9)	0.0547 (6)
H12	1.0044	0.8546	0.5450	0.066*
O13	1.14306 (8)	1.3213 (3)	0.65618 (6)	0.0673 (5)
C14	1.17755 (15)	1.3895 (5)	0.71345 (11)	0.0891 (9)
H14A	1.1475	1.4002	0.7344	0.134*
H14B	1.1975	1.5333	0.7131	0.134*
H14C	1.2109	1.2810	0.7315	0.134*
C15	0.85339 (10)	0.2065 (3)	0.50591 (8)	0.0467 (5)
C16	0.83848 (11)	0.3217 (4)	0.45394 (9)	0.0578 (6)
H16	0.8589	0.4583	0.4527	0.069*
C17	0.79427 (12)	0.2366 (4)	0.40474 (10)	0.0656 (7)
H17	0.7852	0.3163	0.3707	0.079*
C18	0.76293 (11)	0.0351 (4)	0.40476 (9)	0.0565 (6)
C19	0.77751 (12)	−0.0839 (4)	0.45515 (10)	0.0634 (6)
H19	0.7574	−0.2215	0.4558	0.076*
C20	0.82231 (11)	0.0022 (3)	0.50497 (9)	0.0589 (6)
H20	0.8318	−0.0796	0.5388	0.071*
O21	0.71861 (9)	−0.0292 (3)	0.35312 (7)	0.0772 (5)
C22	0.68206 (15)	−0.2275 (5)	0.35211 (12)	0.0921 (9)
H22A	0.7113	−0.3538	0.3622	0.138*
H22B	0.6511	−0.2491	0.3143	0.138*
H22C	0.6591	−0.2140	0.3791	0.138*
N23	0.94146 (8)	0.1510 (3)	0.70559 (7)	0.0532 (5)
C27	0.90703 (10)	−0.0654 (3)	0.70347 (8)	0.0497 (5)
H27	0.9161	−0.1646	0.6754	0.060*
C26	0.94213 (11)	−0.1561 (4)	0.76440 (9)	0.0589 (6)
H26A	0.9112	−0.1843	0.7844	0.071*
H26B	0.9658	−0.2936	0.7633	0.071*
C25	0.98826 (10)	0.0304 (3)	0.79219 (9)	0.0512 (5)
N24	0.98766 (9)	0.1968 (3)	0.75857 (7)	0.0516 (4)
C28	0.83408 (10)	−0.0386 (3)	0.68865 (8)	0.0466 (5)
C29	0.79248 (11)	−0.1969 (4)	0.65509 (10)	0.0594 (6)
H29	0.8099	−0.3149	0.6402	0.071*
C30	0.72521 (12)	−0.1855 (4)	0.64285 (10)	0.0668 (7)
H30	0.6980	−0.2946	0.6200	0.080*
C31	0.69907 (11)	−0.0116 (4)	0.66471 (9)	0.0562 (6)
C32	0.73989 (12)	0.1499 (4)	0.69814 (9)	0.0603 (6)
H32	0.7223	0.2685	0.7127	0.072*
C33	0.80649 (11)	0.1356 (3)	0.70990 (9)	0.0550 (6)
H33	0.8336	0.2452	0.7326	0.066*
O34	0.63314 (8)	0.0149 (3)	0.65443 (8)	0.0832 (6)
C35	0.59055 (14)	−0.1475 (6)	0.61983 (16)	0.1181 (12)
H35A	0.5895	−0.1317	0.5809	0.177*
H35B	0.5472	−0.1264	0.6215	0.177*
H35C	0.6059	−0.2950	0.6335	0.177*
C36	1.03203 (11)	0.0316 (3)	0.85193 (9)	0.0538 (6)
C37	1.02482 (14)	−0.1251 (5)	0.89076 (11)	0.0897 (9)
H37	0.9925	−0.2346	0.8786	0.108*
C38	1.06520 (16)	−0.1204 (5)	0.94740 (11)	0.1114 (13)
H38	1.0594	−0.2262	0.9729	0.134*
C39	1.11359 (13)	0.0376 (4)	0.96645 (10)	0.0758 (7)
C40	1.12168 (12)	0.1934 (4)	0.92856 (10)	0.0691 (7)
H40	1.1545	0.3014	0.9409	0.083*
C41	1.08110 (12)	0.1895 (4)	0.87217 (10)	0.0639 (6)
H41	1.0870	0.2966	0.8470	0.077*
O42	1.15190 (11)	0.0266 (4)	1.02335 (8)	0.1112 (8)
C43	1.20421 (18)	0.1810 (5)	1.04362 (12)	0.1177 (13)
H43A	1.2342	0.1608	1.0229	0.177*
H43B	1.2267	0.1557	1.0837	0.177*
H43C	1.1873	0.3314	1.0380	0.177*

	U11	U22	U33	U12	U13	U23
C1	0.0467 (12)	0.0489 (11)	0.0462 (12)	0.0054 (10)	0.0206 (10)	0.0098 (9)
N2	0.0513 (10)	0.0458 (9)	0.0446 (10)	−0.0002 (8)	0.0177 (8)	0.0078 (8)
C3	0.0433 (11)	0.0430 (11)	0.0447 (12)	0.0081 (9)	0.0155 (9)	0.0088 (9)
C4	0.0552 (13)	0.0519 (12)	0.0435 (12)	0.0034 (10)	0.0169 (10)	0.0124 (9)
C5	0.0438 (12)	0.0453 (11)	0.0441 (12)	0.0104 (9)	0.0149 (9)	0.0071 (9)
N6	0.0482 (10)	0.0526 (9)	0.0419 (10)	0.0018 (8)	0.0155 (8)	0.0061 (8)
C7	0.0402 (11)	0.0468 (11)	0.0455 (12)	0.0065 (9)	0.0150 (9)	0.0073 (9)
C8	0.0665 (15)	0.0661 (14)	0.0468 (13)	−0.0097 (12)	0.0153 (11)	0.0152 (11)
C9	0.0662 (15)	0.0674 (14)	0.0475 (13)	−0.0134 (12)	0.0127 (11)	0.0052 (11)
C10	0.0464 (12)	0.0481 (12)	0.0526 (13)	0.0012 (9)	0.0182 (10)	0.0058 (10)
C11	0.0711 (15)	0.0593 (13)	0.0480 (13)	−0.0093 (12)	0.0218 (11)	0.0112 (10)
C12	0.0629 (14)	0.0584 (13)	0.0411 (12)	−0.0061 (11)	0.0152 (10)	0.0063 (10)
O13	0.0763 (11)	0.0639 (10)	0.0612 (10)	−0.0188 (8)	0.0222 (9)	0.0029 (7)
C14	0.104 (2)	0.0834 (17)	0.0679 (18)	−0.0364 (16)	0.0122 (16)	−0.0077 (14)
C15	0.0478 (12)	0.0482 (11)	0.0442 (12)	0.0069 (10)	0.0155 (10)	0.0061 (9)
C16	0.0634 (14)	0.0560 (12)	0.0500 (13)	−0.0029 (11)	0.0134 (11)	0.0090 (11)
C17	0.0752 (16)	0.0707 (15)	0.0461 (14)	0.0014 (13)	0.0137 (12)	0.0164 (11)
C18	0.0568 (14)	0.0633 (14)	0.0434 (13)	0.0049 (11)	0.0089 (11)	0.0014 (10)
C19	0.0789 (17)	0.0503 (12)	0.0550 (14)	−0.0058 (12)	0.0145 (12)	0.0029 (11)
C20	0.0714 (16)	0.0534 (12)	0.0470 (13)	0.0014 (11)	0.0134 (11)	0.0087 (10)
O21	0.0823 (12)	0.0822 (11)	0.0512 (10)	−0.0099 (10)	0.0010 (9)	0.0016 (8)
C22	0.105 (2)	0.0825 (19)	0.0681 (18)	−0.0162 (17)	0.0016 (16)	−0.0098 (14)
N23	0.0575 (11)	0.0594 (10)	0.0409 (10)	−0.0143 (9)	0.0140 (9)	0.0064 (8)
C27	0.0565 (13)	0.0490 (12)	0.0466 (12)	−0.0042 (10)	0.0212 (10)	0.0023 (9)
C26	0.0574 (14)	0.0606 (13)	0.0562 (14)	−0.0063 (11)	0.0155 (11)	0.0113 (11)
C25	0.0530 (13)	0.0541 (12)	0.0490 (13)	−0.0014 (10)	0.0204 (10)	0.0089 (10)
N24	0.0581 (11)	0.0560 (10)	0.0401 (10)	−0.0057 (9)	0.0158 (8)	0.0038 (8)
C28	0.0556 (13)	0.0496 (11)	0.0373 (11)	−0.0038 (10)	0.0191 (10)	0.0021 (9)
C29	0.0582 (15)	0.0548 (12)	0.0684 (15)	−0.0033 (11)	0.0252 (12)	−0.0180 (11)
C30	0.0598 (15)	0.0649 (14)	0.0764 (17)	−0.0112 (12)	0.0236 (13)	−0.0224 (12)
C31	0.0538 (14)	0.0636 (13)	0.0544 (13)	0.0031 (11)	0.0223 (11)	−0.0043 (11)
C32	0.0676 (16)	0.0597 (13)	0.0557 (14)	0.0069 (12)	0.0234 (12)	−0.0110 (11)
C33	0.0622 (15)	0.0533 (12)	0.0472 (13)	−0.0055 (11)	0.0153 (11)	−0.0088 (10)
O34	0.0555 (11)	0.0960 (13)	0.0997 (14)	0.0022 (9)	0.0278 (10)	−0.0225 (10)
C35	0.0585 (18)	0.125 (3)	0.166 (3)	−0.0159 (18)	0.032 (2)	−0.044 (2)
C36	0.0547 (13)	0.0593 (13)	0.0459 (13)	−0.0015 (11)	0.0149 (10)	0.0080 (10)
C37	0.092 (2)	0.0934 (19)	0.0640 (17)	−0.0369 (16)	0.0006 (15)	0.0306 (14)
C38	0.122 (3)	0.125 (2)	0.0598 (18)	−0.052 (2)	−0.0063 (18)	0.0448 (17)
C39	0.0825 (19)	0.0872 (17)	0.0469 (14)	−0.0161 (15)	0.0075 (13)	0.0133 (13)
C40	0.0721 (16)	0.0742 (15)	0.0548 (15)	−0.0168 (13)	0.0128 (12)	0.0081 (12)
C41	0.0732 (16)	0.0665 (14)	0.0499 (14)	−0.0136 (13)	0.0177 (12)	0.0128 (11)
O42	0.1200 (17)	0.1355 (17)	0.0529 (11)	−0.0441 (14)	−0.0047 (11)	0.0269 (11)
C43	0.137 (3)	0.123 (2)	0.0618 (19)	−0.050 (2)	−0.0081 (19)	0.0032 (17)

C1—N2	1.337 (2)	N23—N24	1.385 (2)
C1—N6	1.347 (2)	N23—C27	1.480 (2)
C1—N23	1.375 (2)	C27—C28	1.505 (3)
N2—C3	1.342 (2)	C27—C26	1.542 (3)
C3—C4	1.396 (3)	C27—H27	0.9800
C3—C7	1.477 (3)	C26—C25	1.498 (3)
C4—C5	1.384 (3)	C26—H26A	0.9700
C4—H4	0.9300	C26—H26B	0.9700
C5—N6	1.346 (2)	C25—N24	1.291 (2)
C5—C15	1.485 (3)	C25—C36	1.465 (3)
C7—C8	1.390 (3)	C28—C29	1.374 (3)
C7—C12	1.393 (3)	C28—C33	1.385 (3)
C8—C9	1.379 (3)	C29—C30	1.386 (3)
C8—H8	0.9300	C29—H29	0.9300
C9—C10	1.377 (3)	C30—C31	1.374 (3)
C9—H9	0.9300	C30—H30	0.9300
C10—O13	1.364 (2)	C31—O34	1.372 (3)
C10—C11	1.380 (3)	C31—C32	1.379 (3)
C11—C12	1.371 (3)	C32—C33	1.374 (3)
C11—H11	0.9300	C32—H32	0.9300
C12—H12	0.9300	C33—H33	0.9300
O13—C14	1.423 (3)	O34—C35	1.411 (3)
C14—H14A	0.9600	C35—H35A	0.9600
C14—H14B	0.9600	C35—H35B	0.9600
C14—H14C	0.9600	C35—H35C	0.9600
C15—C20	1.386 (3)	C36—C41	1.381 (3)
C15—C16	1.397 (3)	C36—C37	1.385 (3)
C16—C17	1.370 (3)	C37—C38	1.382 (3)
C16—H16	0.9300	C37—H37	0.9300
C17—C18	1.378 (3)	C38—C39	1.369 (4)
C17—H17	0.9300	C38—H38	0.9300
C18—O21	1.372 (2)	C39—C40	1.371 (3)
C18—C19	1.376 (3)	C39—O42	1.376 (3)
C19—C20	1.387 (3)	C40—C41	1.379 (3)
C19—H19	0.9300	C40—H40	0.9300
C20—H20	0.9300	C41—H41	0.9300
O21—C22	1.416 (3)	O42—C43	1.414 (3)
C22—H22A	0.9600	C43—H43A	0.9600
C22—H22B	0.9600	C43—H43B	0.9600
C22—H22C	0.9600	C43—H43C	0.9600
N2—C1—N6	127.81 (18)	N23—C27—C28	113.01 (16)
N2—C1—N23	117.79 (18)	N23—C27—C26	101.11 (15)
N6—C1—N23	114.39 (17)	C28—C27—C26	114.17 (17)
C1—N2—C3	115.99 (17)	N23—C27—H27	109.4
N2—C3—C4	120.76 (18)	C28—C27—H27	109.4
N2—C3—C7	115.14 (17)	C26—C27—H27	109.4
C4—C3—C7	124.09 (17)	C25—C26—C27	102.96 (16)
C5—C4—C3	118.79 (18)	C25—C26—H26A	111.2
C5—C4—H4	120.6	C27—C26—H26A	111.2
C3—C4—H4	120.6	C25—C26—H26B	111.2
N6—C5—C4	121.15 (18)	C27—C26—H26B	111.2
N6—C5—C15	115.10 (18)	H26A—C26—H26B	109.1
C4—C5—C15	123.74 (18)	N24—C25—C36	120.68 (19)
C5—N6—C1	115.48 (17)	N24—C25—C26	114.29 (18)
C8—C7—C12	116.12 (19)	C36—C25—C26	125.03 (18)
C8—C7—C3	119.82 (18)	C25—N24—N23	107.92 (17)
C12—C7—C3	124.06 (18)	C29—C28—C33	117.68 (19)
C9—C8—C7	122.6 (2)	C29—C28—C27	119.77 (18)
C9—C8—H8	118.7	C33—C28—C27	122.47 (18)
C7—C8—H8	118.7	C28—C29—C30	121.8 (2)
C10—C9—C8	119.8 (2)	C28—C29—H29	119.1
C10—C9—H9	120.1	C30—C29—H29	119.1
C8—C9—H9	120.1	C31—C30—C29	119.4 (2)
O13—C10—C9	124.22 (19)	C31—C30—H30	120.3
O13—C10—C11	116.93 (18)	C29—C30—H30	120.3
C9—C10—C11	118.8 (2)	O34—C31—C30	123.6 (2)
C12—C11—C10	120.9 (2)	O34—C31—C32	116.7 (2)
C12—C11—H11	119.6	C30—C31—C32	119.7 (2)
C10—C11—H11	119.6	C33—C32—C31	120.0 (2)
C11—C12—C7	121.8 (2)	C33—C32—H32	120.0
C11—C12—H12	119.1	C31—C32—H32	120.0
C7—C12—H12	119.1	C32—C33—C28	121.36 (19)
C10—O13—C14	116.95 (18)	C32—C33—H33	119.3
O13—C14—H14A	109.5	C28—C33—H33	119.3
O13—C14—H14B	109.5	C31—O34—C35	117.50 (19)
H14A—C14—H14B	109.5	O34—C35—H35A	109.5
O13—C14—H14C	109.5	O34—C35—H35B	109.5
H14A—C14—H14C	109.5	H35A—C35—H35B	109.5
H14B—C14—H14C	109.5	O34—C35—H35C	109.5
C20—C15—C16	117.00 (19)	H35A—C35—H35C	109.5
C20—C15—C5	120.63 (18)	H35B—C35—H35C	109.5
C16—C15—C5	122.34 (18)	C41—C36—C37	117.3 (2)
C17—C16—C15	121.0 (2)	C41—C36—C25	121.93 (19)
C17—C16—H16	119.5	C37—C36—C25	120.8 (2)
C15—C16—H16	119.5	C38—C37—C36	120.7 (2)
C16—C17—C18	121.3 (2)	C38—C37—H37	119.6
C16—C17—H17	119.4	C36—C37—H37	119.6
C18—C17—H17	119.4	C39—C38—C37	121.0 (2)
O21—C18—C19	125.3 (2)	C39—C38—H38	119.5
O21—C18—C17	115.70 (19)	C37—C38—H38	119.5
C19—C18—C17	119.0 (2)	C38—C39—C40	119.2 (2)
C18—C19—C20	119.7 (2)	C38—C39—O42	116.7 (2)
C18—C19—H19	120.1	C40—C39—O42	124.1 (2)
C20—C19—H19	120.1	C39—C40—C41	119.8 (2)
C15—C20—C19	122.0 (2)	C39—C40—H40	120.1
C15—C20—H20	119.0	C41—C40—H40	120.1
C19—C20—H20	119.0	C40—C41—C36	122.1 (2)
C18—O21—C22	117.49 (18)	C40—C41—H41	119.0
O21—C22—H22A	109.5	C36—C41—H41	119.0
O21—C22—H22B	109.5	C39—O42—C43	118.0 (2)
H22A—C22—H22B	109.5	O42—C43—H43A	109.5
O21—C22—H22C	109.5	O42—C43—H43B	109.5
H22A—C22—H22C	109.5	H43A—C43—H43B	109.5
H22B—C22—H22C	109.5	O42—C43—H43C	109.5
C1—N23—N24	120.71 (17)	H43A—C43—H43C	109.5
C1—N23—C27	123.77 (16)	H43B—C43—H43C	109.5
N24—N23—C27	113.61 (14)
N6—C1—N2—C3	−1.9 (3)	N2—C1—N23—C27	−172.80 (17)
N23—C1—N2—C3	179.00 (17)	N6—C1—N23—C27	8.0 (3)
C1—N2—C3—C4	1.0 (3)	C1—N23—C27—C28	−75.8 (2)
C1—N2—C3—C7	−179.94 (16)	N24—N23—C27—C28	119.86 (18)
N2—C3—C4—C5	−0.1 (3)	C1—N23—C27—C26	161.72 (19)
C7—C3—C4—C5	−179.10 (17)	N24—N23—C27—C26	−2.6 (2)
C3—C4—C5—N6	−0.1 (3)	N23—C27—C26—C25	3.1 (2)
C3—C4—C5—C15	179.57 (18)	C28—C27—C26—C25	−118.58 (19)
C4—C5—N6—C1	−0.5 (3)	C27—C26—C25—N24	−3.1 (3)
C15—C5—N6—C1	179.76 (16)	C27—C26—C25—C36	177.7 (2)
N2—C1—N6—C5	1.6 (3)	C36—C25—N24—N23	−179.24 (18)
N23—C1—N6—C5	−179.23 (17)	C26—C25—N24—N23	1.5 (3)
N2—C3—C7—C8	−0.9 (3)	C1—N23—N24—C25	−164.00 (19)
C4—C3—C7—C8	178.11 (19)	C27—N23—N24—C25	0.8 (2)
N2—C3—C7—C12	179.56 (19)	N23—C27—C28—C29	143.75 (19)
C4—C3—C7—C12	−1.4 (3)	C26—C27—C28—C29	−101.4 (2)
C12—C7—C8—C9	0.7 (3)	N23—C27—C28—C33	−39.5 (3)
C3—C7—C8—C9	−178.9 (2)	C26—C27—C28—C33	75.3 (2)
C7—C8—C9—C10	−0.9 (4)	C33—C28—C29—C30	−0.4 (3)
C8—C9—C10—O13	179.4 (2)	C27—C28—C29—C30	176.5 (2)
C8—C9—C10—C11	1.0 (3)	C28—C29—C30—C31	0.0 (4)
O13—C10—C11—C12	−179.4 (2)	C29—C30—C31—O34	179.3 (2)
C9—C10—C11—C12	−0.9 (3)	C29—C30—C31—C32	0.4 (4)
C10—C11—C12—C7	0.7 (3)	O34—C31—C32—C33	−179.5 (2)
C8—C7—C12—C11	−0.5 (3)	C30—C31—C32—C33	−0.5 (3)
C3—C7—C12—C11	179.02 (19)	C31—C32—C33—C28	0.2 (3)
C9—C10—O13—C14	−2.3 (3)	C29—C28—C33—C32	0.3 (3)
C11—C10—O13—C14	176.2 (2)	C27—C28—C33—C32	−176.56 (19)
N6—C5—C15—C20	−9.0 (3)	C30—C31—O34—C35	0.5 (4)
C4—C5—C15—C20	171.3 (2)	C32—C31—O34—C35	179.4 (3)
N6—C5—C15—C16	169.18 (19)	N24—C25—C36—C41	−10.5 (3)
C4—C5—C15—C16	−10.5 (3)	C26—C25—C36—C41	168.6 (2)
C20—C15—C16—C17	1.0 (3)	N24—C25—C36—C37	168.4 (2)
C5—C15—C16—C17	−177.3 (2)	C26—C25—C36—C37	−12.5 (3)
C15—C16—C17—C18	0.1 (4)	C41—C36—C37—C38	0.4 (4)
C16—C17—C18—O21	178.4 (2)	C25—C36—C37—C38	−178.5 (3)
C16—C17—C18—C19	−1.2 (4)	C36—C37—C38—C39	−0.5 (5)
O21—C18—C19—C20	−178.5 (2)	C37—C38—C39—C40	0.2 (5)
C17—C18—C19—C20	1.1 (4)	C37—C38—C39—O42	−179.0 (3)
C16—C15—C20—C19	−1.0 (3)	C38—C39—C40—C41	0.2 (4)
C5—C15—C20—C19	177.3 (2)	O42—C39—C40—C41	179.4 (3)
C18—C19—C20—C15	0.0 (4)	C39—C40—C41—C36	−0.3 (4)
C19—C18—O21—C22	3.8 (3)	C37—C36—C41—C40	0.0 (4)
C17—C18—O21—C22	−175.8 (2)	C25—C36—C41—C40	178.9 (2)
N2—C1—N23—N24	−9.5 (3)	C38—C39—O42—C43	177.1 (3)
N6—C1—N23—N24	171.21 (17)	C40—C39—O42—C43	−2.1 (4)