(3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbon-yl]-5-methyl-indolizin-1-yl}methanone.

There are two independent mol-ecules in the asymmetric unit of the title compound, C21H21N5O2. In each mol-ecule, the indolizine ring system is essentially planar, with r.m.s. deviations of 0.030 and 0.028 Å. The dihedral angles between the indolizine ring system and the pyrazole rings are 54.7 (3) and 8.6 (3)° in one mol-ecule and 54.4 (3) and 6.6 (3)° in the other. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds link mol-ecules, forming a two-dimensional network parallel to (100).

Related literature

For the biological applications of indolizines and pyrazoles, see: Tukulula et al. (2010 ▶); James et al. (2008 ▶); Teklu et al. (2005 ▶); McDonald et al. (2006 ▶); Jagerovic et al. (2002 ▶). For background to and the synthesis of related hetrocycles, see: Gu et al. (2011 ▶); Shen et al. (2006 ▶, 2008 ▶); Wang, et al. (2000 ▶).

Experimental

Crystal data

C21H21N5O2

M = 375.43

Orthorhombic,

a = 19.7286 (11) Å

b = 11.5659 (14) Å

c = 17.8088 (18) Å

V = 4063.6 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.979, T max = 0.984

30693 measured reflections

7955 independent reflections

6221 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.129

S = 1.07

7955 reflections

516 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005060/lh5581sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005060/lh5581Isup3.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005060/lh5581Isup4.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005060/lh5581Isup5.cml

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

C21H21N5O2	F(000) = 1584
Mr = 375.43	Dx = 1.227 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5647 reflections
a = 19.7286 (11) Å	θ = 2.3–21.7°
b = 11.5659 (14) Å	µ = 0.08 mm−1
c = 17.8088 (18) Å	T = 291 K
V = 4063.6 (7) Å3	Block, colourless
Z = 8	0.26 × 0.22 × 0.20 mm

Bruker SMART APEX CCD diffractometer	7955 independent reflections
Radiation source: sealed tube	6221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −24→23
Tmin = 0.979, Tmax = 0.984	k = −12→14
30693 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.05P)2 + 1.55P] where P = (Fo2 + 2Fc2)/3
7955 reflections	(Δ/σ)max < 0.001
516 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.95788 (15)	0.4268 (3)	0.79194 (16)	0.0511 (7)
C2	0.97669 (16)	0.5313 (3)	0.81916 (17)	0.0537 (8)
H2	1.0113	0.5345	0.8545	0.064*
C3	0.94637 (15)	0.6336 (3)	0.79647 (17)	0.0504 (7)
H3	0.9599	0.7036	0.8174	0.061*
C4	0.89665 (16)	0.6313 (3)	0.74333 (17)	0.0517 (7)
H4	0.8786	0.7003	0.7254	0.062*
C5	0.87266 (15)	0.5260 (3)	0.71560 (16)	0.0470 (7)
C6	0.82339 (15)	0.4954 (3)	0.66095 (15)	0.0471 (7)
C7	0.82505 (15)	0.3748 (3)	0.65706 (16)	0.0502 (7)
H7	0.7984	0.3307	0.6249	0.060*
C8	0.87156 (15)	0.3292 (3)	0.70735 (17)	0.0479 (7)
C9	0.99612 (15)	0.3185 (2)	0.80885 (16)	0.0487 (7)
H9A	0.9704	0.2717	0.8431	0.073*
H9B	1.0389	0.3378	0.8312	0.073*
H9C	1.0037	0.2763	0.7632	0.073*
C10	0.86911 (16)	0.2129 (3)	0.73751 (17)	0.0506 (7)
C11	0.83518 (16)	0.0113 (3)	0.70175 (17)	0.0524 (7)
C12	0.82865 (17)	−0.0416 (3)	0.63537 (17)	0.0544 (8)
H12	0.8144	−0.1173	0.6278	0.065*
C13	0.84745 (16)	0.0390 (3)	0.57820 (18)	0.0542 (8)
C14	0.82015 (17)	−0.0311 (3)	0.77875 (18)	0.0588 (8)
H14A	0.7998	−0.1064	0.7758	0.088*
H14B	0.7895	0.0213	0.8031	0.088*
H14C	0.8615	−0.0358	0.8070	0.088*
C15	0.85063 (17)	0.0238 (3)	0.49569 (17)	0.0569 (8)
H15A	0.8706	0.0912	0.4733	0.085*
H15B	0.8057	0.0132	0.4763	0.085*
H15C	0.8777	−0.0428	0.4840	0.085*
C16	0.78392 (15)	0.5808 (3)	0.62317 (16)	0.0483 (7)
C17	0.69986 (16)	0.6164 (3)	0.51854 (18)	0.0532 (7)
C18	0.66236 (15)	0.5437 (3)	0.47619 (16)	0.0489 (7)
H18	0.6326	0.5646	0.4381	0.059*
C19	0.67648 (15)	0.4313 (3)	0.50014 (18)	0.0533 (7)
C20	0.70343 (15)	0.7452 (2)	0.51772 (18)	0.0523 (8)
H20A	0.6759	0.7745	0.4776	0.078*
H20B	0.7496	0.7690	0.5104	0.078*
H20C	0.6871	0.7749	0.5647	0.078*
C21	0.64842 (16)	0.3191 (3)	0.47238 (17)	0.0546 (7)
H21A	0.6708	0.2563	0.4974	0.082*
H21B	0.6558	0.3131	0.4192	0.082*
H21C	0.6007	0.3159	0.4827	0.082*
C22	0.41826 (16)	0.5455 (3)	0.49679 (16)	0.0493 (7)
C23	0.39368 (16)	0.4389 (3)	0.48031 (17)	0.0527 (8)
H23	0.3575	0.4325	0.4471	0.063*
C24	0.42111 (17)	0.3377 (3)	0.51186 (18)	0.0545 (8)
H24	0.4041	0.2658	0.4980	0.065*
C25	0.47187 (16)	0.3449 (3)	0.56205 (18)	0.0537 (7)
H25	0.4883	0.2783	0.5849	0.064*
C26	0.50012 (16)	0.4536 (3)	0.57998 (17)	0.0511 (7)
C27	0.55051 (15)	0.4910 (3)	0.63101 (16)	0.0474 (7)
C28	0.55515 (15)	0.6100 (3)	0.62361 (16)	0.0478 (7)
H28	0.5846	0.6570	0.6507	0.057*
C29	0.51025 (14)	0.6481 (3)	0.57084 (17)	0.0480 (7)
C30	0.38317 (16)	0.6508 (3)	0.47244 (16)	0.0529 (7)
H30A	0.3402	0.6306	0.4509	0.079*
H30B	0.4102	0.6902	0.4356	0.079*
H30C	0.3762	0.7006	0.5149	0.079*
C31	0.51566 (15)	0.7556 (3)	0.52786 (17)	0.0503 (7)
C32	0.55300 (16)	0.9622 (3)	0.54312 (16)	0.0525 (7)
C33	0.55914 (16)	1.0296 (3)	0.60368 (18)	0.0557 (8)
H33	0.5725	1.1067	0.6042	0.067*
C34	0.54178 (16)	0.9629 (3)	0.66563 (18)	0.0544 (8)
C35	0.56546 (17)	0.9886 (3)	0.46158 (17)	0.0570 (8)
H35A	0.5848	1.0644	0.4570	0.086*
H35B	0.5233	0.9856	0.4347	0.086*
H35C	0.5962	0.9325	0.4411	0.086*
C36	0.53860 (17)	0.9990 (3)	0.74706 (17)	0.0555 (8)
H36A	0.5834	1.0164	0.7647	0.083*
H36B	0.5199	0.9372	0.7764	0.083*
H36C	0.5105	1.0663	0.7518	0.083*
C37	0.58944 (16)	0.4080 (3)	0.67483 (17)	0.0502 (7)
C38	0.68154 (15)	0.3805 (3)	0.77224 (18)	0.0501 (7)
C39	0.71764 (15)	0.4592 (3)	0.81277 (17)	0.0488 (7)
H39	0.7507	0.4425	0.8484	0.059*
C40	0.69609 (16)	0.5699 (3)	0.79131 (17)	0.0504 (7)
C41	0.68581 (16)	0.2528 (2)	0.77334 (18)	0.0551 (8)
H41A	0.6442	0.2214	0.7925	0.083*
H41B	0.7227	0.2293	0.8050	0.083*
H41C	0.6932	0.2247	0.7233	0.083*
C42	0.71876 (17)	0.6851 (3)	0.81811 (18)	0.0525 (7)
H42A	0.6845	0.7179	0.8499	0.079*
H42B	0.7262	0.7350	0.7758	0.079*
H42C	0.7602	0.6769	0.8459	0.079*
N1	0.90253 (12)	0.4237 (2)	0.74381 (13)	0.0477 (6)
N2	0.85490 (14)	0.1237 (2)	0.68550 (15)	0.0589 (7)
N3	0.86355 (13)	0.1389 (2)	0.60984 (14)	0.0518 (6)
N4	0.73572 (13)	0.5457 (2)	0.56655 (14)	0.0507 (6)
N5	0.72100 (12)	0.4309 (2)	0.55560 (13)	0.0478 (6)
N6	0.47486 (12)	0.5511 (2)	0.54330 (13)	0.0465 (6)
N7	0.53127 (12)	0.8556 (2)	0.56983 (14)	0.0497 (6)
N8	0.52484 (13)	0.8577 (2)	0.64599 (14)	0.0520 (6)
N9	0.63732 (13)	0.4465 (2)	0.72789 (14)	0.0481 (6)
N10	0.64724 (13)	0.5633 (2)	0.74015 (14)	0.0515 (6)
O1	0.87568 (11)	0.18868 (18)	0.80311 (12)	0.0559 (5)
O2	0.78751 (10)	0.68345 (17)	0.63626 (12)	0.0531 (5)
O3	0.51202 (11)	0.76188 (18)	0.46034 (12)	0.0556 (5)
O4	0.58222 (10)	0.30270 (18)	0.66841 (12)	0.0559 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0487 (16)	0.0568 (19)	0.0479 (17)	0.0042 (14)	0.0005 (13)	0.0006 (14)
C2	0.0537 (18)	0.060 (2)	0.0475 (16)	0.0095 (16)	−0.0077 (14)	0.0062 (15)
C3	0.0493 (17)	0.0514 (18)	0.0507 (17)	0.0049 (13)	−0.0012 (14)	0.0048 (14)
C4	0.0563 (17)	0.0508 (18)	0.0479 (16)	0.0081 (14)	0.0041 (14)	0.0021 (14)
C5	0.0477 (16)	0.0447 (17)	0.0487 (16)	0.0059 (13)	0.0069 (13)	0.0018 (13)
C6	0.0491 (16)	0.0463 (16)	0.0458 (16)	0.0060 (13)	0.0026 (13)	0.0044 (13)
C7	0.0487 (17)	0.0537 (18)	0.0483 (17)	0.0001 (14)	0.0011 (14)	0.0025 (14)
C8	0.0518 (17)	0.0440 (17)	0.0481 (16)	0.0029 (13)	0.0025 (13)	0.0031 (13)
C9	0.0539 (17)	0.0483 (17)	0.0437 (15)	−0.0058 (13)	−0.0063 (14)	−0.0008 (13)
C10	0.0561 (17)	0.0475 (17)	0.0483 (17)	0.0033 (13)	−0.0022 (14)	0.0007 (14)
C11	0.0575 (18)	0.0504 (18)	0.0494 (17)	0.0066 (14)	−0.0094 (14)	−0.0073 (14)
C12	0.067 (2)	0.0446 (17)	0.0517 (17)	0.0039 (14)	−0.0111 (15)	−0.0017 (14)
C13	0.0612 (19)	0.0468 (17)	0.0547 (18)	0.0058 (15)	−0.0136 (15)	0.0012 (14)
C14	0.0580 (18)	0.0523 (18)	0.066 (2)	0.0113 (15)	0.0160 (16)	−0.0099 (16)
C15	0.0592 (18)	0.0564 (19)	0.0552 (18)	0.0045 (15)	0.0096 (15)	0.0069 (15)
C16	0.0484 (17)	0.0477 (18)	0.0488 (17)	0.0028 (13)	0.0020 (13)	−0.0016 (14)
C17	0.0559 (18)	0.0517 (18)	0.0520 (17)	−0.0022 (15)	0.0046 (15)	−0.0007 (14)
C18	0.0502 (17)	0.0511 (18)	0.0453 (16)	−0.0023 (13)	−0.0048 (13)	0.0042 (13)
C19	0.0468 (16)	0.058 (2)	0.0550 (18)	0.0021 (14)	−0.0013 (15)	0.0055 (15)
C20	0.0523 (17)	0.0487 (17)	0.0559 (18)	0.0135 (14)	0.0115 (14)	0.0164 (14)
C21	0.0525 (17)	0.0573 (19)	0.0539 (17)	0.0059 (15)	0.0098 (14)	0.0044 (15)
C22	0.0558 (17)	0.0493 (18)	0.0427 (15)	−0.0023 (14)	0.0064 (14)	−0.0066 (13)
C23	0.0522 (17)	0.0539 (19)	0.0519 (18)	−0.0085 (15)	−0.0076 (14)	−0.0168 (15)
C24	0.0609 (18)	0.0454 (18)	0.0572 (18)	−0.0133 (14)	0.0017 (15)	−0.0182 (14)
C25	0.0562 (18)	0.0499 (17)	0.0552 (18)	−0.0071 (14)	0.0003 (15)	−0.0079 (14)
C26	0.0520 (17)	0.0531 (19)	0.0482 (16)	−0.0041 (14)	0.0097 (14)	−0.0098 (14)
C27	0.0509 (17)	0.0446 (16)	0.0468 (16)	−0.0083 (13)	0.0058 (13)	−0.0074 (13)
C28	0.0493 (16)	0.0452 (17)	0.0489 (16)	−0.0076 (13)	0.0021 (13)	−0.0002 (13)
C29	0.0463 (16)	0.0491 (17)	0.0486 (16)	−0.0036 (13)	0.0083 (13)	−0.0023 (13)
C30	0.0591 (18)	0.0541 (18)	0.0454 (16)	0.0058 (15)	−0.0070 (14)	−0.0125 (14)
C31	0.0545 (17)	0.0499 (18)	0.0466 (18)	0.0005 (14)	0.0022 (14)	−0.0026 (13)
C32	0.0569 (18)	0.0515 (19)	0.0492 (17)	−0.0020 (14)	0.0061 (14)	0.0090 (14)
C33	0.0571 (18)	0.0487 (17)	0.0613 (19)	−0.0173 (14)	0.0033 (16)	−0.0021 (15)
C34	0.0593 (19)	0.0457 (18)	0.0582 (18)	−0.0158 (14)	0.0006 (15)	−0.0120 (14)
C35	0.066 (2)	0.0476 (18)	0.0575 (18)	0.0112 (15)	0.0214 (16)	0.0127 (15)
C36	0.0614 (19)	0.0504 (18)	0.0549 (17)	−0.0115 (15)	0.0045 (15)	−0.0142 (14)
C37	0.0562 (18)	0.0437 (18)	0.0507 (17)	−0.0041 (14)	0.0051 (14)	−0.0004 (14)
C38	0.0477 (16)	0.0441 (17)	0.0584 (17)	0.0027 (14)	0.0088 (14)	0.0083 (14)
C39	0.0497 (16)	0.0548 (18)	0.0419 (15)	−0.0073 (14)	−0.0035 (13)	0.0146 (14)
C40	0.0499 (16)	0.0487 (18)	0.0525 (18)	−0.0090 (13)	0.0038 (14)	−0.0005 (14)
C41	0.0500 (16)	0.0517 (18)	0.0637 (19)	0.0089 (14)	0.0074 (14)	0.0190 (16)
C42	0.0588 (18)	0.0482 (17)	0.0506 (17)	−0.0168 (14)	−0.0049 (14)	−0.0025 (14)
N1	0.0485 (14)	0.0555 (15)	0.0391 (12)	0.0067 (11)	0.0028 (11)	0.0020 (11)
N2	0.0690 (18)	0.0496 (16)	0.0581 (17)	0.0013 (13)	−0.0064 (13)	−0.0029 (13)
N3	0.0610 (16)	0.0441 (14)	0.0503 (14)	0.0074 (11)	−0.0173 (12)	−0.0014 (11)
N4	0.0544 (15)	0.0466 (15)	0.0512 (14)	0.0010 (11)	0.0023 (12)	0.0004 (11)
N5	0.0492 (14)	0.0463 (14)	0.0479 (14)	0.0052 (11)	−0.0036 (11)	0.0062 (11)
N6	0.0497 (14)	0.0427 (14)	0.0472 (14)	−0.0042 (11)	0.0043 (11)	−0.0100 (11)
N7	0.0535 (14)	0.0441 (14)	0.0517 (14)	−0.0040 (11)	0.0011 (12)	0.0037 (11)
N8	0.0593 (15)	0.0440 (14)	0.0527 (15)	−0.0081 (12)	−0.0017 (12)	−0.0063 (11)
N9	0.0506 (13)	0.0431 (14)	0.0505 (14)	0.0012 (11)	0.0022 (11)	0.0038 (11)
N10	0.0580 (16)	0.0457 (15)	0.0506 (14)	−0.0040 (12)	−0.0046 (12)	−0.0042 (11)
O1	0.0595 (13)	0.0548 (12)	0.0535 (13)	0.0116 (10)	0.0011 (10)	−0.0043 (10)
O2	0.0549 (12)	0.0458 (13)	0.0587 (12)	0.0054 (9)	−0.0090 (10)	0.0019 (10)
O3	0.0619 (13)	0.0538 (13)	0.0512 (13)	−0.0047 (10)	0.0072 (10)	0.0049 (10)
O4	0.0599 (13)	0.0477 (13)	0.0602 (13)	0.0003 (10)	−0.0137 (11)	−0.0006 (10)

C1—C2	1.354 (4)	C22—C30	1.467 (4)
C1—N1	1.389 (4)	C23—C24	1.406 (4)
C1—C9	1.493 (4)	C23—H23	0.9300
C2—C3	1.387 (4)	C24—C25	1.345 (4)
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.363 (4)	C25—C26	1.412 (4)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.397 (4)	C26—N6	1.395 (4)
C4—H4	0.9300	C26—C27	1.415 (4)
C5—N1	1.414 (4)	C27—C28	1.386 (4)
C5—C6	1.420 (4)	C27—C37	1.456 (4)
C6—C7	1.397 (4)	C28—C29	1.365 (4)
C6—C16	1.427 (4)	C28—H28	0.9300
C7—C8	1.387 (4)	C29—N6	1.410 (4)
C7—H7	0.9300	C29—C31	1.463 (4)
C8—N1	1.411 (4)	C30—H30A	0.9600
C8—C10	1.448 (4)	C30—H30B	0.9600
C9—H9A	0.9600	C30—H30C	0.9600
C9—H9B	0.9600	C31—O3	1.207 (3)
C9—H9C	0.9600	C31—N7	1.411 (4)
C10—O1	1.209 (3)	C32—C33	1.337 (4)
C10—N2	1.415 (4)	C32—N7	1.389 (4)
C11—C12	1.337 (4)	C32—C35	1.504 (4)
C11—N2	1.387 (4)	C33—C34	1.389 (4)
C11—C14	1.486 (4)	C33—H33	0.9300
C12—C13	1.429 (4)	C34—N8	1.310 (4)
C12—H12	0.9300	C34—C36	1.510 (4)
C13—N3	1.324 (4)	C35—H35A	0.9600
C13—C15	1.481 (4)	C35—H35B	0.9600
C14—H14A	0.9600	C35—H35C	0.9600
C14—H14B	0.9600	C36—H36A	0.9600
C14—H14C	0.9600	C36—H36B	0.9600
C15—H15A	0.9600	C36—H36C	0.9600
C15—H15B	0.9600	C37—O4	1.231 (3)
C15—H15C	0.9600	C37—N9	1.408 (4)
C16—O2	1.212 (3)	C38—C39	1.363 (4)
C16—N4	1.444 (4)	C38—N9	1.403 (4)
C17—C18	1.350 (4)	C38—C41	1.480 (4)
C17—N4	1.379 (4)	C39—C40	1.402 (4)
C17—C20	1.491 (4)	C39—H39	0.9300
C18—C19	1.395 (4)	C40—N10	1.328 (4)
C18—H18	0.9300	C40—C42	1.484 (4)
C19—N5	1.322 (4)	C41—H41A	0.9600
C19—C21	1.495 (4)	C41—H41B	0.9600
C20—H20A	0.9600	C41—H41C	0.9600
C20—H20B	0.9600	C42—H42A	0.9600
C20—H20C	0.9600	C42—H42B	0.9600
C21—H21A	0.9600	C42—H42C	0.9600
C21—H21B	0.9600	N2—N3	1.370 (4)
C21—H21C	0.9600	N4—N5	1.373 (3)
C22—C23	1.357 (4)	N7—N8	1.362 (3)
C22—N6	1.392 (4)	N9—N10	1.382 (3)
C2—C1—N1	117.3 (3)	C26—C25—H25	120.0
C2—C1—C9	122.6 (3)	N6—C26—C25	118.2 (3)
N1—C1—C9	120.0 (3)	N6—C26—C27	107.7 (3)
C1—C2—C3	122.6 (3)	C25—C26—C27	134.0 (3)
C1—C2—H2	118.7	C28—C27—C26	106.8 (3)
C3—C2—H2	118.7	C28—C27—C37	132.2 (3)
C4—C3—C2	119.7 (3)	C26—C27—C37	120.9 (3)
C4—C3—H3	120.1	C29—C28—C27	110.1 (3)
C2—C3—H3	120.1	C29—C28—H28	125.0
C3—C4—C5	120.4 (3)	C27—C28—H28	125.0
C3—C4—H4	119.8	C28—C29—N6	107.7 (3)
C5—C4—H4	119.8	C28—C29—C31	126.0 (3)
C4—C5—N1	117.6 (3)	N6—C29—C31	122.0 (3)
C4—C5—C6	133.7 (3)	C22—C30—H30A	109.5
N1—C5—C6	108.7 (3)	C22—C30—H30B	109.5
C7—C6—C5	105.5 (2)	H30A—C30—H30B	109.5
C7—C6—C16	132.9 (3)	C22—C30—H30C	109.5
C5—C6—C16	121.6 (3)	H30A—C30—H30C	109.5
C8—C7—C6	111.3 (3)	H30B—C30—H30C	109.5
C8—C7—H7	124.3	O3—C31—N7	119.4 (3)
C6—C7—H7	124.3	O3—C31—C29	124.6 (3)
C7—C8—N1	106.8 (3)	N7—C31—C29	115.8 (3)
C7—C8—C10	124.8 (3)	C33—C32—N7	105.6 (3)
N1—C8—C10	124.3 (3)	C33—C32—C35	130.2 (3)
C1—C9—H9A	109.5	N7—C32—C35	124.2 (3)
C1—C9—H9B	109.5	C32—C33—C34	107.1 (3)
H9A—C9—H9B	109.5	C32—C33—H33	126.5
C1—C9—H9C	109.5	C34—C33—H33	126.5
H9A—C9—H9C	109.5	N8—C34—C33	111.5 (3)
H9B—C9—H9C	109.5	N8—C34—C36	120.2 (3)
O1—C10—N2	119.0 (3)	C33—C34—C36	128.2 (3)
O1—C10—C8	124.8 (3)	C32—C35—H35A	109.5
N2—C10—C8	116.2 (3)	C32—C35—H35B	109.5
C12—C11—N2	105.7 (3)	H35A—C35—H35B	109.5
C12—C11—C14	130.2 (3)	C32—C35—H35C	109.5
N2—C11—C14	123.9 (3)	H35A—C35—H35C	109.5
C11—C12—C13	107.8 (3)	H35B—C35—H35C	109.5
C11—C12—H12	126.1	C34—C36—H36A	109.5
C13—C12—H12	126.1	C34—C36—H36B	109.5
N3—C13—C12	109.2 (3)	H36A—C36—H36B	109.5
N3—C13—C15	121.0 (3)	C34—C36—H36C	109.5
C12—C13—C15	129.8 (3)	H36A—C36—H36C	109.5
C11—C14—H14A	109.5	H36B—C36—H36C	109.5
C11—C14—H14B	109.5	O4—C37—N9	116.9 (3)
H14A—C14—H14B	109.5	O4—C37—C27	122.8 (3)
C11—C14—H14C	109.5	N9—C37—C27	120.3 (2)
H14A—C14—H14C	109.5	C39—C38—N9	105.1 (3)
H14B—C14—H14C	109.5	C39—C38—C41	129.1 (3)
C13—C15—H15A	109.5	N9—C38—C41	125.9 (3)
C13—C15—H15B	109.5	C38—C39—C40	107.9 (3)
H15A—C15—H15B	109.5	C38—C39—H39	126.1
C13—C15—H15C	109.5	C40—C39—H39	126.1
H15A—C15—H15C	109.5	N10—C40—C39	110.7 (3)
H15B—C15—H15C	109.5	N10—C40—C42	119.4 (3)
O2—C16—C6	123.8 (3)	C39—C40—C42	129.8 (3)
O2—C16—N4	116.6 (3)	C38—C41—H41A	109.5
C6—C16—N4	119.6 (3)	C38—C41—H41B	109.5
C18—C17—N4	104.9 (3)	H41A—C41—H41B	109.5
C18—C17—C20	130.0 (3)	C38—C41—H41C	109.5
N4—C17—C20	125.1 (3)	H41A—C41—H41C	109.5
C17—C18—C19	107.4 (3)	H41B—C41—H41C	109.5
C17—C18—H18	126.3	C40—C42—H42A	109.5
C19—C18—H18	126.3	C40—C42—H42B	109.5
N5—C19—C18	111.4 (3)	H42A—C42—H42B	109.5
N5—C19—C21	119.3 (3)	C40—C42—H42C	109.5
C18—C19—C21	129.3 (3)	H42A—C42—H42C	109.5
C17—C20—H20A	109.5	H42B—C42—H42C	109.5
C17—C20—H20B	109.5	C1—N1—C8	130.1 (3)
H20A—C20—H20B	109.5	C1—N1—C5	121.7 (3)
C17—C20—H20C	109.5	C8—N1—C5	107.7 (2)
H20A—C20—H20C	109.5	N3—N2—C11	111.1 (3)
H20B—C20—H20C	109.5	N3—N2—C10	121.7 (3)
C19—C21—H21A	109.5	C11—N2—C10	127.1 (3)
C19—C21—H21B	109.5	C13—N3—N2	106.1 (3)
H21A—C21—H21B	109.5	N5—N4—C17	112.2 (2)
C19—C21—H21C	109.5	N5—N4—C16	120.7 (2)
H21A—C21—H21C	109.5	C17—N4—C16	127.1 (3)
H21B—C21—H21C	109.5	C19—N5—N4	104.1 (2)
C23—C22—N6	117.2 (3)	C22—N6—C26	121.9 (2)
C23—C22—C30	121.5 (3)	C22—N6—C29	129.9 (2)
N6—C22—C30	121.1 (3)	C26—N6—C29	107.7 (2)
C22—C23—C24	122.1 (3)	N8—N7—C32	110.7 (2)
C22—C23—H23	118.9	N8—N7—C31	121.4 (2)
C24—C23—H23	118.9	C32—N7—C31	127.8 (3)
C25—C24—C23	120.1 (3)	C34—N8—N7	105.0 (2)
C25—C24—H24	120.0	N10—N9—C38	110.8 (2)
C23—C24—H24	120.0	N10—N9—C37	120.7 (2)
C24—C25—C26	119.9 (3)	C38—N9—C37	128.5 (2)
C24—C25—H25	120.0	C40—N10—N9	105.5 (2)
N1—C1—C2—C3	−5.0 (5)	C7—C8—N1—C5	1.3 (3)
C9—C1—C2—C3	172.0 (3)	C10—C8—N1—C5	−156.7 (3)
C1—C2—C3—C4	−1.7 (5)	C4—C5—N1—C1	−5.9 (4)
C2—C3—C4—C5	4.7 (4)	C6—C5—N1—C1	172.6 (2)
C3—C4—C5—N1	−1.0 (4)	C4—C5—N1—C8	−179.0 (3)
C3—C4—C5—C6	−179.0 (3)	C6—C5—N1—C8	−0.5 (3)
C4—C5—C6—C7	177.7 (3)	C12—C11—N2—N3	−2.8 (4)
N1—C5—C6—C7	−0.4 (3)	C14—C11—N2—N3	−178.4 (3)
C4—C5—C6—C16	−2.8 (5)	C12—C11—N2—C10	−179.1 (3)
N1—C5—C6—C16	179.1 (3)	C14—C11—N2—C10	5.3 (5)
C5—C6—C7—C8	1.3 (3)	O1—C10—N2—N3	−163.3 (3)
C16—C6—C7—C8	−178.2 (3)	C8—C10—N2—N3	19.4 (4)
C6—C7—C8—N1	−1.6 (3)	O1—C10—N2—C11	12.6 (5)
C6—C7—C8—C10	156.2 (3)	C8—C10—N2—C11	−164.6 (3)
C7—C8—C10—O1	−132.8 (3)	C12—C13—N3—N2	−0.4 (3)
N1—C8—C10—O1	21.3 (5)	C15—C13—N3—N2	179.7 (3)
C7—C8—C10—N2	44.2 (4)	C11—N2—N3—C13	2.0 (3)
N1—C8—C10—N2	−161.7 (3)	C10—N2—N3—C13	178.5 (3)
N2—C11—C12—C13	2.4 (4)	C18—C17—N4—N5	−0.6 (3)
C14—C11—C12—C13	177.6 (3)	C20—C17—N4—N5	178.5 (3)
C11—C12—C13—N3	−1.3 (4)	C18—C17—N4—C16	179.4 (3)
C11—C12—C13—C15	178.6 (3)	C20—C17—N4—C16	−1.5 (5)
C7—C6—C16—O2	176.7 (3)	O2—C16—N4—N5	−170.5 (3)
C5—C6—C16—O2	−2.6 (5)	C6—C16—N4—N5	8.6 (4)
C7—C6—C16—N4	−2.3 (5)	O2—C16—N4—C17	9.5 (4)
C5—C6—C16—N4	178.3 (3)	C6—C16—N4—C17	−171.4 (3)
N4—C17—C18—C19	0.3 (3)	C18—C19—N5—N4	−0.4 (3)
C20—C17—C18—C19	−178.7 (3)	C21—C19—N5—N4	180.0 (3)
C17—C18—C19—N5	0.1 (4)	C17—N4—N5—C19	0.6 (3)
C17—C18—C19—C21	179.6 (3)	C16—N4—N5—C19	−179.4 (2)
N6—C22—C23—C24	3.7 (4)	C23—C22—N6—C26	−8.6 (4)
C30—C22—C23—C24	−170.9 (3)	C30—C22—N6—C26	166.0 (3)
C22—C23—C24—C25	2.3 (5)	C23—C22—N6—C29	−178.7 (3)
C23—C24—C25—C26	−3.5 (5)	C30—C22—N6—C29	−4.1 (4)
C24—C25—C26—N6	−1.2 (5)	C25—C26—N6—C22	7.5 (4)
C24—C25—C26—C27	177.0 (3)	C27—C26—N6—C22	−171.2 (2)
N6—C26—C27—C28	−0.6 (3)	C25—C26—N6—C29	179.5 (3)
C25—C26—C27—C28	−178.9 (3)	C27—C26—N6—C29	0.8 (3)
N6—C26—C27—C37	−176.4 (3)	C28—C29—N6—C22	170.4 (3)
C25—C26—C27—C37	5.3 (5)	C31—C29—N6—C22	−31.7 (4)
C26—C27—C28—C29	0.1 (3)	C28—C29—N6—C26	−0.8 (3)
C37—C27—C28—C29	175.2 (3)	C31—C29—N6—C26	157.1 (3)
C27—C28—C29—N6	0.4 (3)	C33—C32—N7—N8	−0.6 (4)
C27—C28—C29—C31	−156.4 (3)	C35—C32—N7—N8	179.7 (3)
C28—C29—C31—O3	128.1 (4)	C33—C32—N7—C31	178.3 (3)
N6—C29—C31—O3	−25.6 (5)	C35—C32—N7—C31	−1.5 (5)
C28—C29—C31—N7	−47.0 (4)	O3—C31—N7—N8	168.8 (3)
N6—C29—C31—N7	159.3 (3)	C29—C31—N7—N8	−15.8 (4)
N7—C32—C33—C34	0.6 (4)	O3—C31—N7—C32	−9.9 (5)
C35—C32—C33—C34	−179.7 (3)	C29—C31—N7—C32	165.4 (3)
C32—C33—C34—N8	−0.4 (4)	C33—C34—N8—N7	0.0 (4)
C32—C33—C34—C36	−178.3 (3)	C36—C34—N8—N7	178.1 (3)
C28—C27—C37—O4	−172.3 (3)	C32—N7—N8—C34	0.3 (3)
C26—C27—C37—O4	2.2 (5)	C31—N7—N8—C34	−178.6 (3)
C28—C27—C37—N9	8.3 (5)	C39—C38—N9—N10	1.2 (3)
C26—C27—C37—N9	−177.1 (3)	C41—C38—N9—N10	−179.3 (3)
N9—C38—C39—C40	−1.4 (3)	C39—C38—N9—C37	179.0 (3)
C41—C38—C39—C40	179.2 (3)	C41—C38—N9—C37	−1.5 (5)
C38—C39—C40—N10	1.2 (4)	O4—C37—N9—N10	−178.2 (3)
C38—C39—C40—C42	179.9 (3)	C27—C37—N9—N10	1.1 (4)
C2—C1—N1—C8	−179.8 (3)	O4—C37—N9—C38	4.1 (5)
C9—C1—N1—C8	3.1 (4)	C27—C37—N9—C38	−176.5 (3)
C2—C1—N1—C5	8.8 (4)	C39—C40—N10—N9	−0.4 (3)
C9—C1—N1—C5	−168.3 (3)	C42—C40—N10—N9	−179.3 (3)
C7—C8—N1—C1	−171.1 (3)	C38—N9—N10—C40	−0.5 (3)
C10—C8—N1—C1	31.0 (5)	C37—N9—N10—C40	−178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.37	3.282 (4)	167
C21—H21B···O1ii	0.96	2.59	3.404 (4)	142
C30—H30C···N3iii	0.96	2.52	3.472 (4)	169
C33—H33···O4iv	0.93	2.55	3.393 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.37	3.282 (4)	167
C21—H21B⋯O1ii	0.96	2.59	3.404 (4)	142
C30—H30C⋯N3iii	0.96	2.52	3.472 (4)	169
C33—H33⋯O4iv	0.93	2.55	3.393 (4)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .