3-[5-Methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-5-[4-(piperidin-1-yl)phen-yl]-4,5-dihydro-1H-pyrazole-1-carbothio-amide dimethyl-formamide hemisolvate.

The essentially planar pyrazole ring (r.m.s. deviation = 0.013 Å) in the title hemisolvate, C(31)H(33)N(7)S·0.5C(3)H(7)NO, is almost coplanar with the pendant thio-urea residue [N-N-C-S torsion angle = -173.2 (4)°] and slightly twisted with respect to the triazole ring [dihedral angle = 7.7 (3)°]. An intra-molecular thio-urea-pyrazole N-H⋯N hydrogen bond, via an S(5) loop, is formed. Supra-molecular chains along the c axis are formed in the crystal via piperidine-triazole C-H⋯N inter-actions. These are bridged into loosely associated double chains via C-H⋯O inter-actions involving the disordered (over two positions) dimethyl-formamide solvent mol-ecules. The thio-urea-bound phenyl ring is also disordered over two positions of equal occupancy.

Related literature

For the biological activity of related compounds, see: Abdel-Wahab et al. (2009 ▶, 2012a ▶). For a related pyrazolyl-1,2,3-triazole structure, see: Abdel-Wahab et al. (2012b ▶).

Experimental

Crystal data

C31H33N7S·0.5C3H7NO

M = 522.26

Monoclinic,

a = 42.077 (4) Å

b = 5.9274 (5) Å

c = 12.0737 (11) Å

β = 105.665 (9)°

V = 2899.5 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.29 mm−1

T = 100 K

0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.661, T max = 0.938

10437 measured reflections

3317 independent reflections

3229 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.091

wR(F 2) = 0.214

S = 1.11

3317 reflections

396 parameters

41 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −1.06 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024488/xu5554sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024488/xu5554Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024488/xu5554Isup3.cml

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

C31H33N7S·0.5C3H7NO	F(000) = 1216
Mr = 522.26	Dx = 1.311 Mg m−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: C 2y	Cell parameters from 6358 reflections
a = 42.077 (4) Å	θ = 3.8–76.9°
b = 5.9274 (5) Å	µ = 1.29 mm−1
c = 12.0737 (11) Å	T = 100 K
β = 105.665 (9)°	Prism, light-brown
V = 2899.5 (4) Å3	0.35 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3317 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3229 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.4041 pixels mm-1	θmax = 77.1°, θmin = 3.8°
ω scan	h = −52→49
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −5→7
Tmin = 0.661, Tmax = 0.938	l = −14→15
10437 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)] = 0.091	H-atom parameters constrained
wR(F2) = 0.214	w = 1/[σ2(Fo2) + (0.0422P)2 + 29.4613P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
3317 reflections	Δρmax = 0.71 e Å−3
396 parameters	Δρmin = −1.06 e Å−3
41 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00150 (17)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.59659 (4)	0.0014 (4)	0.47105 (16)	0.0329 (5)
N1	0.56945 (14)	0.4011 (13)	0.5037 (5)	0.0306 (14)
H1	0.5726	0.5285	0.5426	0.037*
N2	0.61985 (13)	0.3203 (11)	0.6223 (5)	0.0250 (13)
N3	0.61644 (13)	0.5210 (12)	0.6819 (5)	0.0251 (12)
N4	0.67600 (14)	0.7524 (12)	0.9292 (5)	0.0282 (13)
N5	0.67224 (14)	0.9126 (13)	1.0004 (5)	0.0304 (14)
N6	0.64025 (13)	0.9852 (13)	0.9628 (5)	0.0267 (13)
N7	0.72517 (13)	0.4072 (12)	0.3176 (5)	0.0261 (13)
C1	0.53887 (17)	0.3838 (17)	0.4206 (10)	0.0259 (16)	0.50
C2	0.5261 (2)	0.2040 (15)	0.3484 (10)	0.029 (2)	0.50
H2	0.5391	0.0727	0.3489	0.035*	0.50
C3	0.4944 (2)	0.2165 (17)	0.2753 (9)	0.036 (3)	0.50
H3	0.4856	0.0936	0.2259	0.043*	0.50
C4	0.47537 (19)	0.409 (2)	0.2745 (10)	0.032 (3)	0.50
H4	0.4537	0.4172	0.2245	0.038*	0.50
C5	0.4881 (2)	0.5885 (16)	0.3467 (10)	0.034 (3)	0.50
H5	0.4752	0.7199	0.3462	0.041*	0.50
C6	0.5199 (2)	0.5761 (14)	0.4198 (9)	0.029 (2)	0.50
H6	0.5286	0.6989	0.4692	0.035*	0.50
C1'	0.53743 (17)	0.3832 (17)	0.4284 (9)	0.0259 (16)	0.50
C2'	0.5190 (2)	0.1876 (15)	0.4256 (9)	0.029 (2)	0.50
H2'	0.5279	0.0650	0.4749	0.035*	0.50
C3'	0.4875 (2)	0.1716 (15)	0.3507 (10)	0.036 (3)	0.50
H3'	0.4749	0.0380	0.3489	0.043*	0.50
C4'	0.4745 (2)	0.3511 (19)	0.2787 (10)	0.032 (3)	0.50
H4'	0.4530	0.3401	0.2275	0.038*	0.50
C5'	0.4929 (2)	0.5466 (16)	0.2814 (9)	0.034 (3)	0.50
H5'	0.4840	0.6693	0.2322	0.041*	0.50
C6'	0.5244 (2)	0.5627 (14)	0.3563 (10)	0.029 (2)	0.50
H6'	0.5370	0.6963	0.3582	0.035*	0.50
C7	0.59446 (16)	0.2551 (14)	0.5330 (6)	0.0261 (15)
C8	0.65420 (15)	0.2319 (14)	0.6552 (6)	0.0252 (15)
H8	0.6543	0.0662	0.6708	0.030*
C9	0.66858 (15)	0.3640 (15)	0.7684 (6)	0.0281 (16)
H9A	0.6707	0.2663	0.8366	0.034*
H9B	0.6904	0.4294	0.7710	0.034*
C10	0.64330 (16)	0.5443 (13)	0.7621 (5)	0.0240 (15)
C11	0.64669 (17)	0.7263 (13)	0.8469 (6)	0.0246 (14)
C12	0.62375 (16)	0.8719 (14)	0.8666 (6)	0.0263 (15)
C13	0.58794 (16)	0.9065 (15)	0.8053 (6)	0.0305 (16)
H13A	0.5758	0.9465	0.8612	0.046*
H13B	0.5788	0.7670	0.7656	0.046*
H13C	0.5858	1.0285	0.7490	0.046*
C14	0.62887 (16)	1.1423 (14)	1.0318 (6)	0.0276 (16)
C15	0.61095 (18)	1.3329 (15)	0.9829 (7)	0.0327 (17)
H15	0.6065	1.3611	0.9027	0.039*
C16	0.59990 (19)	1.4774 (16)	1.0516 (7)	0.0354 (17)
H16	0.5872	1.6041	1.0173	0.043*
C17	0.6065 (2)	1.4476 (13)	1.1719 (8)	0.0363 (19)
C18	0.6245 (2)	1.2523 (16)	1.2175 (7)	0.0360 (18)
H18	0.6292	1.2239	1.2977	0.043*
C19	0.63557 (19)	1.1015 (16)	1.1493 (6)	0.0343 (17)
H19	0.6476	0.9712	1.1822	0.041*
C20	0.5944 (2)	1.6067 (17)	1.2460 (8)	0.047 (2)
H20A	0.5827	1.5227	1.2929	0.071*
H20B	0.5793	1.7156	1.1977	0.071*
H20C	0.6131	1.6871	1.2964	0.071*
C21	0.67202 (16)	0.2810 (14)	0.5649 (6)	0.0269 (16)
C22	0.67004 (19)	0.4876 (16)	0.5091 (7)	0.0350 (17)
H22	0.6565	0.6026	0.5273	0.042*
C23	0.68695 (17)	0.5317 (14)	0.4285 (6)	0.0305 (16)
H23	0.6848	0.6751	0.3921	0.037*
C24	0.70737 (16)	0.3670 (14)	0.3994 (6)	0.0258 (15)
C25	0.70995 (18)	0.1619 (14)	0.4574 (6)	0.0291 (16)
H25	0.7240	0.0480	0.4417	0.035*
C26	0.69243 (17)	0.1197 (13)	0.5380 (6)	0.0280 (15)
H26	0.6946	−0.0229	0.5751	0.034*
C27	0.71379 (18)	0.5951 (15)	0.2389 (7)	0.0318 (17)
H27A	0.7099	0.7279	0.2832	0.038*
H27B	0.6925	0.5540	0.1838	0.038*
C28	0.73850 (18)	0.6574 (14)	0.1727 (6)	0.0293 (16)
H28A	0.7592	0.7105	0.2270	0.035*
H28B	0.7295	0.7818	0.1187	0.035*
C29	0.74577 (18)	0.4548 (15)	0.1060 (6)	0.0333 (19)
H29A	0.7254	0.4055	0.0486	0.040*
H29B	0.7624	0.4954	0.0650	0.040*
C30	0.75863 (18)	0.2688 (15)	0.1902 (6)	0.0307 (17)
H30A	0.7801	0.3149	0.2423	0.037*
H30B	0.7624	0.1328	0.1479	0.037*
C31	0.73474 (18)	0.2102 (14)	0.2620 (7)	0.0313 (17)
H31A	0.7147	0.1397	0.2115	0.038*
H31B	0.7453	0.0985	0.3215	0.038*
O1	0.5327 (3)	0.8817 (18)	0.9722 (10)	0.051 (3)	0.50
N8	0.4987 (3)	1.1815 (15)	0.9647 (8)	0.039 (4)	0.50
C32	0.5278 (3)	1.0766 (18)	1.0017 (9)	0.041 (4)	0.50
H32	0.5455	1.1547	1.0528	0.049*	0.50
C33	0.4703 (3)	1.078 (3)	0.8870 (13)	0.051 (5)	0.50
H33A	0.4768	0.9346	0.8593	0.077*	0.50
H33B	0.4615	1.1789	0.8215	0.077*	0.50
H33C	0.4534	1.0509	0.9274	0.077*	0.50
C34	0.4944 (4)	1.4106 (18)	1.002 (2)	0.043 (5)	0.50
H34A	0.5155	1.4673	1.0499	0.064*	0.50
H34B	0.4780	1.4107	1.0460	0.064*	0.50
H34C	0.4867	1.5079	0.9341	0.064*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0282 (8)	0.0365 (10)	0.0366 (9)	−0.0056 (9)	0.0133 (7)	−0.0043 (9)
N1	0.025 (3)	0.035 (4)	0.035 (3)	−0.002 (3)	0.013 (2)	−0.005 (3)
N2	0.020 (3)	0.028 (3)	0.029 (3)	0.000 (3)	0.012 (2)	−0.006 (3)
N3	0.024 (3)	0.026 (3)	0.029 (3)	−0.003 (3)	0.012 (2)	−0.002 (3)
N4	0.026 (3)	0.027 (3)	0.035 (3)	0.002 (3)	0.013 (2)	−0.004 (3)
N5	0.024 (3)	0.033 (4)	0.036 (3)	0.001 (3)	0.012 (2)	−0.004 (3)
N6	0.023 (3)	0.031 (3)	0.029 (3)	0.001 (3)	0.012 (2)	0.004 (3)
N7	0.025 (3)	0.026 (3)	0.031 (3)	0.003 (3)	0.013 (2)	0.004 (3)
C1	0.023 (3)	0.028 (4)	0.030 (4)	0.005 (3)	0.014 (3)	0.000 (3)
C2	0.029 (5)	0.025 (5)	0.032 (5)	0.000 (4)	0.009 (4)	−0.001 (5)
C3	0.030 (6)	0.033 (6)	0.043 (6)	0.003 (5)	0.006 (5)	−0.002 (6)
C4	0.026 (4)	0.031 (8)	0.036 (4)	0.001 (5)	0.005 (3)	−0.002 (5)
C5	0.030 (5)	0.030 (6)	0.047 (7)	0.000 (5)	0.019 (5)	0.003 (6)
C6	0.032 (5)	0.022 (5)	0.039 (7)	−0.006 (4)	0.017 (5)	−0.001 (5)
C1'	0.023 (3)	0.028 (4)	0.030 (4)	0.005 (3)	0.014 (3)	0.000 (3)
C2'	0.029 (5)	0.025 (5)	0.032 (5)	0.000 (4)	0.009 (4)	−0.001 (5)
C3'	0.030 (6)	0.033 (6)	0.043 (6)	0.003 (5)	0.006 (5)	−0.002 (6)
C4'	0.026 (4)	0.031 (8)	0.036 (4)	0.001 (5)	0.005 (3)	−0.002 (5)
C5'	0.030 (5)	0.030 (6)	0.047 (7)	0.000 (5)	0.019 (5)	0.003 (6)
C6'	0.032 (5)	0.022 (5)	0.039 (7)	−0.006 (4)	0.017 (5)	−0.001 (5)
C7	0.024 (3)	0.032 (4)	0.030 (3)	−0.003 (3)	0.019 (3)	0.000 (3)
C8	0.016 (3)	0.031 (4)	0.030 (3)	0.001 (3)	0.010 (3)	0.002 (3)
C9	0.016 (3)	0.040 (5)	0.030 (3)	−0.001 (3)	0.008 (2)	−0.001 (3)
C10	0.023 (3)	0.029 (4)	0.024 (3)	0.000 (3)	0.012 (2)	−0.001 (3)
C11	0.026 (3)	0.024 (4)	0.027 (3)	0.004 (3)	0.011 (3)	0.001 (3)
C12	0.022 (3)	0.034 (4)	0.024 (3)	−0.006 (3)	0.009 (3)	0.006 (3)
C13	0.024 (3)	0.033 (4)	0.038 (4)	−0.001 (3)	0.014 (3)	−0.006 (4)
C14	0.021 (3)	0.027 (4)	0.039 (4)	−0.003 (3)	0.014 (3)	−0.005 (3)
C15	0.028 (4)	0.031 (4)	0.044 (4)	0.004 (3)	0.019 (3)	0.004 (4)
C16	0.037 (4)	0.028 (4)	0.048 (4)	0.001 (4)	0.023 (3)	0.002 (4)
C17	0.048 (4)	0.014 (4)	0.057 (5)	−0.002 (3)	0.032 (4)	−0.009 (3)
C18	0.045 (4)	0.034 (4)	0.035 (4)	−0.005 (4)	0.020 (3)	−0.002 (4)
C19	0.037 (4)	0.034 (4)	0.034 (4)	0.001 (4)	0.012 (3)	−0.001 (4)
C20	0.065 (6)	0.034 (5)	0.058 (5)	0.000 (5)	0.044 (5)	−0.001 (5)
C21	0.020 (3)	0.029 (4)	0.032 (4)	−0.003 (3)	0.007 (3)	0.000 (3)
C22	0.036 (4)	0.026 (4)	0.050 (4)	0.003 (4)	0.025 (3)	−0.002 (4)
C23	0.031 (3)	0.025 (4)	0.041 (4)	0.000 (3)	0.019 (3)	0.001 (3)
C24	0.019 (3)	0.027 (4)	0.033 (3)	0.000 (3)	0.012 (3)	0.004 (3)
C25	0.029 (4)	0.024 (4)	0.040 (4)	0.004 (3)	0.019 (3)	−0.002 (3)
C26	0.029 (3)	0.021 (4)	0.040 (4)	0.004 (3)	0.018 (3)	0.005 (3)
C27	0.031 (4)	0.030 (4)	0.038 (4)	−0.001 (3)	0.017 (3)	0.006 (4)
C28	0.026 (3)	0.032 (4)	0.033 (4)	0.002 (3)	0.014 (3)	0.005 (3)
C29	0.029 (3)	0.041 (5)	0.032 (3)	0.003 (3)	0.011 (3)	0.005 (4)
C30	0.027 (3)	0.032 (4)	0.037 (4)	0.001 (3)	0.015 (3)	0.004 (4)
C31	0.030 (4)	0.027 (4)	0.043 (4)	−0.001 (3)	0.020 (3)	0.000 (3)
O1	0.046 (6)	0.048 (7)	0.059 (6)	0.003 (6)	0.017 (5)	−0.019 (6)
N8	0.038 (6)	0.033 (6)	0.050 (7)	−0.003 (6)	0.017 (6)	−0.012 (5)
C32	0.038 (7)	0.041 (8)	0.043 (7)	−0.012 (6)	0.010 (6)	−0.009 (6)
C33	0.048 (8)	0.052 (9)	0.056 (8)	0.000 (7)	0.019 (7)	−0.006 (7)
C34	0.045 (11)	0.039 (7)	0.055 (7)	0.005 (6)	0.032 (7)	−0.003 (8)

S1—C7	1.693 (8)	C13—H13C	0.9800
N1—C7	1.334 (10)	C14—C19	1.391 (10)
N1—C1	1.405 (8)	C14—C15	1.398 (11)
N1—C1'	1.411 (8)	C15—C16	1.359 (11)
N1—H1	0.8800	C15—H15	0.9500
N2—C7	1.354 (9)	C16—C17	1.414 (11)
N2—N3	1.417 (8)	C16—H16	0.9500
N2—C8	1.487 (8)	C17—C18	1.412 (12)
N3—C10	1.282 (8)	C17—C20	1.482 (11)
N4—N5	1.318 (9)	C18—C19	1.378 (11)
N4—C11	1.368 (9)	C18—H18	0.9500
N5—N6	1.369 (8)	C19—H19	0.9500
N6—C12	1.359 (9)	C20—H20A	0.9800
N6—C14	1.416 (10)	C20—H20B	0.9800
N7—C24	1.411 (8)	C20—H20C	0.9800
N7—C31	1.458 (10)	C21—C26	1.382 (10)
N7—C27	1.458 (10)	C21—C22	1.389 (12)
C1—C2	1.3900	C22—C23	1.378 (10)
C1—C6	1.3900	C22—H22	0.9500
C2—C3	1.3900	C23—C24	1.406 (10)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.3900	C24—C25	1.393 (11)
C3—H3	0.9500	C25—C26	1.392 (9)
C4—C5	1.3900	C25—H25	0.9500
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.3900	C27—C28	1.518 (9)
C5—H5	0.9500	C27—H27A	0.9900
C6—H6	0.9500	C27—H27B	0.9900
C1'—C2'	1.3900	C28—C29	1.522 (11)
C1'—C6'	1.3900	C28—H28A	0.9900
C2'—C3'	1.3900	C28—H28B	0.9900
C2'—H2'	0.9500	C29—C30	1.498 (11)
C3'—C4'	1.3900	C29—H29A	0.9900
C3'—H3'	0.9500	C29—H29B	0.9900
C4'—C5'	1.3900	C30—C31	1.534 (9)
C4'—H4'	0.9500	C30—H30A	0.9900
C5'—C6'	1.3900	C30—H30B	0.9900
C5'—H5'	0.9500	C31—H31A	0.9900
C6'—H6'	0.9500	C31—H31B	0.9900
C8—C21	1.509 (9)	O1—C32	1.242 (9)
C8—C9	1.550 (10)	N8—C32	1.338 (8)
C8—H8	1.0000	N8—C33	1.442 (9)
C9—C10	1.495 (10)	N8—C34	1.456 (9)
C9—H9A	0.9900	C32—H32	0.9500
C9—H9B	0.9900	C33—H33A	0.9800
C10—C11	1.467 (10)	C33—H33B	0.9800
C11—C12	1.363 (10)	C33—H33C	0.9800
C12—C13	1.503 (9)	C34—H34A	0.9800
C13—H13A	0.9800	C34—H34B	0.9800
C13—H13B	0.9800	C34—H34C	0.9800
C7—N1—C1	130.3 (8)	C12—C13—H13C	109.5
C7—N1—C1'	132.0 (8)	H13A—C13—H13C	109.5
C1—N1—C1'	5.1 (9)	H13B—C13—H13C	109.5
C7—N1—H1	114.9	C19—C14—C15	120.6 (7)
C1—N1—H1	114.9	C19—C14—N6	118.5 (7)
C1'—N1—H1	112.9	C15—C14—N6	120.8 (7)
C7—N2—N3	118.5 (6)	C16—C15—C14	119.1 (7)
C7—N2—C8	127.8 (6)	C16—C15—H15	120.5
N3—N2—C8	112.6 (5)	C14—C15—H15	120.5
C10—N3—N2	106.5 (6)	C15—C16—C17	123.0 (8)
N5—N4—C11	108.2 (6)	C15—C16—H16	118.5
N4—N5—N6	106.9 (6)	C17—C16—H16	118.5
C12—N6—N5	111.0 (6)	C18—C17—C16	116.0 (7)
C12—N6—C14	130.6 (6)	C18—C17—C20	121.5 (8)
N5—N6—C14	118.1 (6)	C16—C17—C20	122.5 (8)
C24—N7—C31	116.9 (6)	C19—C18—C17	122.1 (7)
C24—N7—C27	116.2 (6)	C19—C18—H18	119.0
C31—N7—C27	113.2 (6)	C17—C18—H18	119.0
C2—C1—C6	120.0	C18—C19—C14	119.2 (8)
C2—C1—N1	128.9 (7)	C18—C19—H19	120.4
C6—C1—N1	111.0 (7)	C14—C19—H19	120.4
C1—C2—C3	120.0	C17—C20—H20A	109.5
C1—C2—H2	120.0	C17—C20—H20B	109.5
C3—C2—H2	120.0	H20A—C20—H20B	109.5
C4—C3—C2	120.0	C17—C20—H20C	109.5
C4—C3—H3	120.0	H20A—C20—H20C	109.5
C2—C3—H3	120.0	H20B—C20—H20C	109.5
C5—C4—C3	120.0	C26—C21—C22	117.1 (6)
C5—C4—H4	120.0	C26—C21—C8	119.9 (7)
C3—C4—H4	120.0	C22—C21—C8	122.9 (7)
C4—C5—C6	120.0	C23—C22—C21	122.3 (8)
C4—C5—H5	120.0	C23—C22—H22	118.8
C6—C5—H5	120.0	C21—C22—H22	118.8
C5—C6—C1	120.0	C22—C23—C24	120.8 (8)
C5—C6—H6	120.0	C22—C23—H23	119.6
C1—C6—H6	120.0	C24—C23—H23	119.6
C2'—C1'—C6'	120.0	C25—C24—C23	116.7 (6)
C2'—C1'—N1	120.5 (7)	C25—C24—N7	121.0 (6)
C6'—C1'—N1	119.5 (7)	C23—C24—N7	122.2 (7)
C3'—C2'—C1'	120.0	C24—C25—C26	121.6 (7)
C3'—C2'—H2'	120.0	C24—C25—H25	119.2
C1'—C2'—H2'	120.0	C26—C25—H25	119.2
C4'—C3'—C2'	120.0	C21—C26—C25	121.3 (7)
C4'—C3'—H3'	120.0	C21—C26—H26	119.3
C2'—C3'—H3'	120.0	C25—C26—H26	119.3
C5'—C4'—C3'	120.0	N7—C27—C28	112.2 (6)
C5'—C4'—H4'	120.0	N7—C27—H27A	109.2
C3'—C4'—H4'	120.0	C28—C27—H27A	109.2
C4'—C5'—C6'	120.0	N7—C27—H27B	109.2
C4'—C5'—H5'	120.0	C28—C27—H27B	109.2
C6'—C5'—H5'	120.0	H27A—C27—H27B	107.9
C5'—C6'—C1'	120.0	C27—C28—C29	110.5 (7)
C5'—C6'—H6'	120.0	C27—C28—H28A	109.5
C1'—C6'—H6'	120.0	C29—C28—H28A	109.5
N2—C7—N1	115.0 (7)	C27—C28—H28B	109.5
N2—C7—S1	118.8 (6)	C29—C28—H28B	109.5
N1—C7—S1	126.2 (6)	H28A—C28—H28B	108.1
N2—C8—C21	112.1 (6)	C30—C29—C28	108.0 (6)
N2—C8—C9	100.2 (5)	C30—C29—H29A	110.1
C21—C8—C9	112.9 (6)	C28—C29—H29A	110.1
N2—C8—H8	110.4	C30—C29—H29B	110.1
C21—C8—H8	110.4	C28—C29—H29B	110.1
C9—C8—H8	110.4	H29A—C29—H29B	108.4
C10—C9—C8	102.3 (5)	C29—C30—C31	112.2 (6)
C10—C9—H9A	111.3	C29—C30—H30A	109.2
C8—C9—H9A	111.3	C31—C30—H30A	109.2
C10—C9—H9B	111.3	C29—C30—H30B	109.2
C8—C9—H9B	111.3	C31—C30—H30B	109.2
H9A—C9—H9B	109.2	H30A—C30—H30B	107.9
N3—C10—C11	120.4 (6)	N7—C31—C30	112.6 (7)
N3—C10—C9	115.6 (6)	N7—C31—H31A	109.1
C11—C10—C9	123.8 (6)	C30—C31—H31A	109.1
C12—C11—N4	110.1 (6)	N7—C31—H31B	109.1
C12—C11—C10	130.3 (6)	C30—C31—H31B	109.1
N4—C11—C10	119.3 (6)	H31A—C31—H31B	107.8
N6—C12—C11	103.9 (6)	C32—N8—C33	122.9 (9)
N6—C12—C13	124.6 (7)	C32—N8—C34	120.7 (10)
C11—C12—C13	131.6 (7)	C33—N8—C34	116.4 (12)
C12—C13—H13A	109.5	O1—C32—N8	123.0 (10)
C12—C13—H13B	109.5	O1—C32—H32	118.5
H13A—C13—H13B	109.5	N8—C32—H32	118.5
C7—N2—N3—C10	179.4 (6)	C9—C10—C11—N4	8.2 (10)
C8—N2—N3—C10	−11.2 (7)	N5—N6—C12—C11	0.3 (8)
C11—N4—N5—N6	0.6 (8)	C14—N6—C12—C11	−173.0 (8)
N4—N5—N6—C12	−0.6 (8)	N5—N6—C12—C13	178.3 (7)
N4—N5—N6—C14	173.7 (6)	C14—N6—C12—C13	5.0 (12)
C7—N1—C1—C2	2.2 (15)	N4—C11—C12—N6	0.1 (8)
C1'—N1—C1—C2	−110 (7)	C10—C11—C12—N6	173.6 (7)
C7—N1—C1—C6	179.2 (7)	N4—C11—C12—C13	−177.7 (7)
C1'—N1—C1—C6	67 (7)	C10—C11—C12—C13	−4.2 (13)
C6—C1—C2—C3	0.0	C12—N6—C14—C19	125.9 (8)
N1—C1—C2—C3	176.8 (13)	N5—N6—C14—C19	−47.1 (10)
C1—C2—C3—C4	0.0	C12—N6—C14—C15	−53.4 (11)
C2—C3—C4—C5	0.0	N5—N6—C14—C15	133.7 (7)
C3—C4—C5—C6	0.0	C19—C14—C15—C16	−0.5 (11)
C4—C5—C6—C1	0.0	N6—C14—C15—C16	178.7 (7)
C2—C1—C6—C5	0.0	C14—C15—C16—C17	1.8 (12)
N1—C1—C6—C5	−177.4 (11)	C15—C16—C17—C18	−2.1 (12)
C7—N1—C1'—C2'	41.5 (13)	C15—C16—C17—C20	179.8 (8)
C1—N1—C1'—C2'	114 (7)	C16—C17—C18—C19	1.1 (12)
C7—N1—C1'—C6'	−138.2 (8)	C20—C17—C18—C19	179.2 (8)
C1—N1—C1'—C6'	−66 (7)	C17—C18—C19—C14	0.1 (12)
C6'—C1'—C2'—C3'	0.0	C15—C14—C19—C18	−0.5 (11)
N1—C1'—C2'—C3'	−179.8 (11)	N6—C14—C19—C18	−179.7 (7)
C1'—C2'—C3'—C4'	0.0	N2—C8—C21—C26	−139.9 (7)
C2'—C3'—C4'—C5'	0.0	C9—C8—C21—C26	107.8 (8)
C3'—C4'—C5'—C6'	0.0	N2—C8—C21—C22	42.8 (10)
C4'—C5'—C6'—C1'	0.0	C9—C8—C21—C22	−69.5 (9)
C2'—C1'—C6'—C5'	0.0	C26—C21—C22—C23	1.3 (12)
N1—C1'—C6'—C5'	179.8 (11)	C8—C21—C22—C23	178.7 (7)
N3—N2—C7—N1	5.7 (9)	C21—C22—C23—C24	−0.4 (12)
C8—N2—C7—N1	−161.8 (6)	C22—C23—C24—C25	−1.2 (11)
N3—N2—C7—S1	−173.2 (4)	C22—C23—C24—N7	−179.6 (7)
C8—N2—C7—S1	19.2 (9)	C31—N7—C24—C25	24.7 (10)
C1—N1—C7—N2	−176.3 (9)	C27—N7—C24—C25	162.7 (7)
C1'—N1—C7—N2	−169.9 (9)	C31—N7—C24—C23	−156.9 (7)
C1—N1—C7—S1	2.6 (12)	C27—N7—C24—C23	−18.9 (10)
C1'—N1—C7—S1	8.9 (12)	C23—C24—C25—C26	1.8 (11)
C7—N2—C8—C21	64.7 (10)	N7—C24—C25—C26	−179.7 (7)
N3—N2—C8—C21	−103.4 (7)	C22—C21—C26—C25	−0.7 (11)
C7—N2—C8—C9	−175.3 (7)	C8—C21—C26—C25	−178.2 (7)
N3—N2—C8—C9	16.5 (7)	C24—C25—C26—C21	−0.9 (12)
N2—C8—C9—C10	−14.7 (7)	C24—N7—C27—C28	167.4 (6)
C21—C8—C9—C10	104.7 (7)	C31—N7—C27—C28	−53.1 (8)
N2—N3—C10—C11	−174.5 (6)	N7—C27—C28—C29	57.4 (8)
N2—N3—C10—C9	0.0 (8)	C27—C28—C29—C30	−58.0 (8)
C8—C9—C10—N3	10.2 (8)	C28—C29—C30—C31	55.9 (9)
C8—C9—C10—C11	−175.6 (6)	C24—N7—C31—C30	−170.6 (6)
N5—N4—C11—C12	−0.5 (8)	C27—N7—C31—C30	50.2 (8)
N5—N4—C11—C10	−174.8 (6)	C29—C30—C31—N7	−52.8 (9)
N3—C10—C11—C12	9.2 (11)	C33—N8—C32—O1	−0.1 (4)
C9—C10—C11—C12	−164.8 (7)	C34—N8—C32—O1	−179.8 (3)
N3—C10—C11—N4	−177.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.88	2.13	2.597 (8)	112
C13—H13A···O1	0.98	2.56	3.466 (14)	154
C28—H28B···N5i	0.99	2.57	3.355 (10)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.88	2.13	2.597 (8)	112
C13—H13A⋯O1	0.98	2.56	3.466 (14)	154
C28—H28B⋯N5i	0.99	2.57	3.355 (10)	137

Symmetry code: (i) .