4-(Pyridin-2-yl)­thia­zol-2-yl­amine

At 150 K, the asymmetric unit of the crystal structure of the title compound, C₈H₇N₃S, comprises three mol­ecules. All the amine N-H groups and heterocyclic N atoms are involved in intermolecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.083
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S3     in Main Residue .          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C8 H7 N3 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-RED (Stoe & Cie, 2001); cell refinement: X-RED; data reduction: X-RED; program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX.

4-(Pyridin-2-yl)thiazol-2-ylamine

Crystal data

C8H7N3S	F(000) = 1104
Mr = 177.23	Dx = 1.456 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 22342 reflections
a = 13.2392 (10) Å	θ = 2.1–30.0°
b = 13.7499 (9) Å	µ = 0.34 mm^−1
c = 14.1126 (12) Å	T = 150 K
β = 109.268 (6)°	Block, colourless
V = 2425.1 (3) Å^3	0.60 × 0.55 × 0.50 mm
Z = 12

Data collection

Stoe IPDS II area detector diffractometer	5224 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.077
Graphite monochromator	θmax = 30.0°, θmin = 2.1°
ω scans	h = −17→18
25877 measured reflections	k = −17→19
7032 independent reflections	l = −19→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0456P)^2] where P = (Fo^2 + 2Fc^2)/3
7032 reflections	(Δ/σ)max = 0.002
349 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 190 frames (2 minute exposure) were collected (phi/omega: 70/0–140, 90/100–150, delta-omega = 1 °.)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807).

Plane 1 Atom d s d/s (d/s)**2 C1 * -0.0057 0.0013 - 4.549 20.689 C2 * -0.0036 0.0013 - 2.837 8.050 C3 * 0.0005 0.0011 0.422 0.178 S1 * 0.0005 0.0004 1.166 1.360 N2 * 0.0031 0.0011 2.815 7.924 N1 - 0.0608 0.0014 - 44.753 2002.856 ============ Sum((d/s)**2) for starred atoms 38.201 Chi-squared at 95% for 2 degrees of freedom: 5.99

Plane 2 Atom d s d/s (d/s)**2 N3 * -0.0157 0.0011 - 14.675 215.345 C4 * 0.0126 0.0011 11.829 139.918 C5 * 0.0010 0.0012 0.854 0.729 C6 * -0.0173 0.0013 - 12.935 167.323 C7 * 0.0125 0.0013 9.330 87.041 C8 * 0.0083 0.0013 6.221 38.703 C3 0.1189 0.0011 111.114 12346.299 ============ Sum((d/s)**2) for starred atoms 649.060 Chi-squared at 95% for 3 degrees of freedom: 7.81

Plane 3 Atom d s d/s (d/s)**2 S2 * 0.0000 0.0003 0.065 0.004 N5 * -0.0013 0.0010 - 1.306 1.705 C9 * 0.0010 0.0013 0.762 0.581 C10 * -0.0016 0.0013 - 1.263 1.596 C11 * 0.0022 0.0012 1.791 3.208 N4 0.0305 0.0013 24.297 590.327 C12 0.0059 0.0013 4.699 22.077 ============ Sum((d/s)**2) for starred atoms 7.094 Chi-squared at 95% for 2 degrees of freedom: 5.99

Plane 4 Atom d s d/s (d/s)**2 N6 * 0.0017 0.0011 1.545 2.389 C12 * 0.0029 0.0012 2.363 5.584 C13 * -0.0046 0.0013 - 3.651 13.330 C14 * 0.0015 0.0013 1.102 1.215 C15 * 0.0048 0.0014 3.371 11.364 C16 * -0.0080 0.0015 - 5.325 28.352 C11 - 0.0123 0.0012 - 10.571 111.741 ============ Sum((d/s)**2) for starred atoms 62.234 Chi-squared at 95% for 3 degrees of freedom: 7.81

Plane 5 Atom d s d/s (d/s)**2 S3 * 0.0007 0.0004 1.849 3.420 N8 * 0.0028 0.0011 2.615 6.840 C17 * -0.0071 0.0012 - 5.863 34.369 C18 * -0.0067 0.0012 - 5.528 30.555 C19 * 0.0027 0.0011 2.490 6.202 N7 - 0.0279 0.0013 - 21.015 441.621 C20 0.1053 0.0011 97.934 9591.019 ============ Sum((d/s)**2) for starred atoms 81.385 Chi-squared at 95% for 2 degrees of freedom: 5.99

Plane 6 Atom d s d/s (d/s)**2 N9 * -0.0060 0.0012 - 4.977 24.770 C20 * 0.0053 0.0011 4.902 24.033 C21 * -0.0019 0.0012 - 1.597 2.550 C22 * -0.0039 0.0013 - 2.938 8.633 C23 * 0.0055 0.0015 3.760 14.139 C24 * 0.0014 0.0016 0.901 0.811 C19 0.1118 0.0011 103.111 10631.935 ============ Sum((d/s)**2) for starred atoms 74.936 Chi-squared at 95% for 3 degrees of freedom: 7.81

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 22.23 (0.04) 157.77 (0.04) 1 3 26.08 (0.04) 153.92 (0.04) 1 4 12.07 (0.04) 167.93 (0.04) 1 5 30.57 (0.03) 149.43 (0.03) 1 6 15.07 (0.04) 164.93 (0.04) 2 3 47.93 (0.04) 132.07 (0.04) 2 4 34.13 (0.04) 145.87 (0.04) 2 5 16.05 (0.04) 163.95 (0.04) 2 6 7.61 (0.04) 172.39 (0.04) 3 4 14.02 (0.04) 165.98 (0.04) 3 5 51.93 (0.03) 128.07 (0.03) 3 6 41.10 (0.04) 138.90 (0.04) 4 5 40.14 (0.03) 139.86 (0.03) 4 6 27.13 (0.04) 152.87 (0.04) 5 6 21.08 (0.04) 158.92 (0.04)

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 > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.07146 (3)	0.88897 (2)	0.37692 (3)	0.02902 (8)
S2	0.56105 (3)	1.08128 (2)	0.79668 (2)	0.02410 (7)
S3	0.20566 (3)	0.39367 (2)	0.39001 (3)	0.02809 (8)
N1	0.17864 (11)	1.05001 (9)	0.46779 (10)	0.0316 (3)
H1A	0.2364 (17)	1.0771 (14)	0.5125 (15)	0.047 (5)*
H1B	0.1236 (15)	1.0820 (13)	0.4441 (13)	0.035 (5)*
N2	0.27577 (9)	0.90876 (7)	0.46105 (8)	0.0228 (2)
N3	0.32837 (9)	0.65308 (8)	0.42695 (8)	0.0255 (2)
N4	0.46339 (10)	0.96418 (8)	0.63890 (9)	0.0296 (3)
H4A	0.4070 (14)	0.9500 (12)	0.5855 (13)	0.029 (4)*
H4B	0.5117 (15)	0.9232 (13)	0.6639 (13)	0.034 (5)*
N5	0.37263 (8)	1.10366 (7)	0.66458 (7)	0.0210 (2)
N6	0.33852 (9)	1.34074 (8)	0.76945 (8)	0.0248 (2)
N7	0.12113 (11)	0.54960 (9)	0.45429 (10)	0.0308 (3)
H7A	0.0816 (16)	0.5689 (15)	0.4903 (15)	0.044 (5)*
H7B	0.1783 (17)	0.5796 (14)	0.4556 (14)	0.043 (5)*
N8	0.02282 (9)	0.40379 (7)	0.41879 (8)	0.0218 (2)
N9	−0.03269 (9)	0.14641 (8)	0.36266 (9)	0.0269 (2)
C1	0.18586 (11)	0.95719 (9)	0.44056 (9)	0.0235 (2)
C2	0.15218 (11)	0.78946 (9)	0.38054 (9)	0.0247 (3)
H2	0.1274	0.7271	0.3539	0.030*
C3	0.25609 (10)	0.81353 (9)	0.42704 (8)	0.0213 (2)
C4	0.34775 (10)	0.74961 (8)	0.43541 (8)	0.0210 (2)
C5	0.44831 (11)	0.78943 (9)	0.44728 (9)	0.0239 (2)
H5	0.4593	0.8577	0.4542	0.029*
C6	0.53198 (12)	0.72782 (10)	0.44881 (10)	0.0273 (3)
H6	0.6016	0.7528	0.4586	0.033*
C7	0.51150 (12)	0.62894 (10)	0.43577 (10)	0.0292 (3)
H7	0.5661	0.5850	0.4339	0.035*
C8	0.40983 (12)	0.59563 (9)	0.42560 (10)	0.0292 (3)
H8	0.3968	0.5277	0.4171	0.035*
C9	0.45533 (10)	1.04497 (9)	0.68960 (9)	0.0209 (2)
C10	0.48700 (10)	1.18169 (9)	0.80636 (9)	0.0231 (2)
H10	0.5099	1.2301	0.8570	0.028*
C11	0.39108 (10)	1.18170 (8)	0.73105 (8)	0.0200 (2)
C12	0.30854 (10)	1.25720 (8)	0.71687 (9)	0.0203 (2)
C13	0.20354 (10)	1.24213 (9)	0.65314 (9)	0.0236 (2)
H13	0.1841	1.1826	0.6175	0.028*
C14	0.12834 (11)	1.31492 (10)	0.64257 (9)	0.0264 (3)
H14	0.0569	1.3061	0.5992	0.032*
C15	0.15837 (12)	1.40080 (10)	0.69582 (10)	0.0282 (3)
H15	0.1086	1.4521	0.6896	0.034*
C16	0.26391 (12)	1.40925 (9)	0.75862 (11)	0.0283 (3)
H16	0.2843	1.4675	0.7963	0.034*
C17	0.10750 (10)	0.45581 (9)	0.42439 (9)	0.0227 (2)
C18	0.12626 (11)	0.29072 (9)	0.36876 (9)	0.0244 (2)
H18	0.1446	0.2297	0.3474	0.029*
C19	0.03418 (10)	0.30984 (9)	0.38706 (8)	0.0201 (2)
C20	−0.05547 (10)	0.24101 (8)	0.36908 (8)	0.0205 (2)
C21	−0.15976 (11)	0.27357 (9)	0.35358 (9)	0.0250 (2)
H21	−0.1736	0.3407	0.3594	0.030*
C22	−0.24263 (11)	0.20673 (10)	0.32962 (10)	0.0279 (3)
H22	−0.3140	0.2273	0.3190	0.034*
C23	−0.22003 (12)	0.10977 (10)	0.32138 (11)	0.0295 (3)
H23	−0.2753	0.0624	0.3043	0.035*
C24	−0.11460 (12)	0.08352 (10)	0.33869 (12)	0.0326 (3)
H24	−0.0993	0.0167	0.3332	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02244 (17)	0.02504 (15)	0.03392 (16)	0.00207 (12)	0.00165 (12)	−0.00563 (12)
S2	0.02084 (15)	0.02190 (14)	0.02503 (14)	0.00077 (11)	0.00146 (11)	−0.00137 (11)
S3	0.02449 (17)	0.02323 (15)	0.04060 (18)	−0.00118 (12)	0.01621 (13)	−0.00392 (13)
N1	0.0285 (7)	0.0217 (5)	0.0363 (6)	0.0057 (5)	−0.0008 (5)	−0.0064 (5)
N2	0.0246 (6)	0.0192 (5)	0.0224 (5)	0.0008 (4)	0.0048 (4)	−0.0015 (4)
N3	0.0276 (6)	0.0193 (5)	0.0273 (5)	0.0009 (4)	0.0058 (4)	0.0002 (4)
N4	0.0235 (6)	0.0224 (5)	0.0352 (6)	0.0043 (4)	−0.0007 (5)	−0.0086 (4)
N5	0.0201 (5)	0.0176 (4)	0.0238 (5)	−0.0011 (4)	0.0052 (4)	−0.0019 (4)
N6	0.0244 (6)	0.0205 (5)	0.0303 (5)	−0.0017 (4)	0.0101 (4)	−0.0032 (4)
N7	0.0316 (7)	0.0205 (5)	0.0452 (7)	−0.0034 (5)	0.0191 (5)	−0.0070 (5)
N8	0.0223 (5)	0.0182 (4)	0.0254 (5)	0.0016 (4)	0.0087 (4)	−0.0011 (4)
N9	0.0239 (6)	0.0195 (5)	0.0356 (6)	0.0010 (4)	0.0075 (4)	−0.0008 (4)
C1	0.0254 (7)	0.0206 (5)	0.0214 (5)	0.0013 (5)	0.0035 (4)	−0.0018 (4)
C2	0.0270 (7)	0.0199 (5)	0.0248 (5)	0.0004 (5)	0.0055 (5)	−0.0027 (4)
C3	0.0255 (6)	0.0190 (5)	0.0187 (5)	0.0008 (4)	0.0064 (4)	0.0004 (4)
C4	0.0257 (6)	0.0193 (5)	0.0175 (5)	0.0017 (4)	0.0066 (4)	0.0008 (4)
C5	0.0294 (7)	0.0202 (5)	0.0243 (5)	0.0005 (5)	0.0117 (5)	0.0016 (4)
C6	0.0280 (7)	0.0292 (6)	0.0274 (6)	0.0019 (5)	0.0127 (5)	0.0035 (5)
C7	0.0316 (7)	0.0263 (6)	0.0312 (6)	0.0077 (5)	0.0125 (5)	0.0014 (5)
C8	0.0328 (8)	0.0191 (6)	0.0339 (6)	0.0028 (5)	0.0086 (5)	−0.0008 (5)
C9	0.0186 (6)	0.0182 (5)	0.0243 (5)	−0.0023 (4)	0.0049 (4)	0.0002 (4)
C10	0.0233 (6)	0.0219 (5)	0.0233 (5)	0.0000 (4)	0.0065 (4)	−0.0028 (4)
C11	0.0213 (6)	0.0180 (5)	0.0215 (5)	−0.0017 (4)	0.0083 (4)	−0.0003 (4)
C12	0.0219 (6)	0.0187 (5)	0.0217 (5)	−0.0009 (4)	0.0091 (4)	−0.0003 (4)
C13	0.0232 (6)	0.0254 (6)	0.0225 (5)	−0.0012 (5)	0.0078 (4)	−0.0022 (4)
C14	0.0236 (6)	0.0310 (6)	0.0241 (5)	0.0039 (5)	0.0072 (4)	0.0039 (5)
C15	0.0295 (7)	0.0242 (6)	0.0337 (6)	0.0061 (5)	0.0142 (5)	0.0047 (5)
C16	0.0303 (7)	0.0199 (6)	0.0371 (7)	−0.0013 (5)	0.0145 (5)	−0.0035 (5)
C17	0.0229 (6)	0.0198 (5)	0.0257 (5)	0.0029 (4)	0.0084 (5)	0.0004 (4)
C18	0.0254 (6)	0.0196 (5)	0.0299 (6)	0.0001 (5)	0.0116 (5)	−0.0028 (4)
C19	0.0215 (6)	0.0194 (5)	0.0190 (5)	0.0015 (4)	0.0062 (4)	0.0001 (4)
C20	0.0226 (6)	0.0195 (5)	0.0187 (5)	0.0014 (4)	0.0058 (4)	−0.0004 (4)
C21	0.0252 (6)	0.0230 (6)	0.0273 (6)	0.0024 (5)	0.0093 (5)	−0.0015 (5)
C22	0.0220 (6)	0.0303 (7)	0.0320 (6)	0.0014 (5)	0.0096 (5)	0.0005 (5)
C23	0.0255 (7)	0.0262 (6)	0.0359 (7)	−0.0053 (5)	0.0088 (5)	−0.0001 (5)
C24	0.0290 (7)	0.0191 (6)	0.0468 (8)	−0.0002 (5)	0.0086 (6)	−0.0009 (5)

Geometric parameters (Å, º)

S1—C2	1.7265 (13)	C4—C5	1.3975 (19)
S1—C1	1.7557 (13)	C5—C6	1.3890 (19)
S2—C10	1.7247 (13)	C5—H5	0.9500
S2—C9	1.7595 (12)	C6—C7	1.3867 (19)
S3—C18	1.7294 (13)	C6—H6	0.9500
S3—C17	1.7523 (13)	C7—C8	1.384 (2)
N1—C1	1.3452 (17)	C7—H7	0.9500
N1—H1A	0.90 (2)	C8—H8	0.9500
N1—H1B	0.822 (19)	C10—C11	1.3607 (17)
N2—C1	1.3104 (17)	C10—H10	0.9500
N2—C3	1.3894 (15)	C11—C12	1.4722 (17)
N3—C8	1.3419 (18)	C12—C13	1.3998 (17)
N3—C4	1.3497 (16)	C13—C14	1.3846 (18)
N4—C9	1.3446 (16)	C13—H13	0.9500
N4—H4A	0.890 (17)	C14—C15	1.3857 (19)
N4—H4B	0.837 (18)	C14—H14	0.9500
N5—C9	1.3113 (16)	C15—C16	1.391 (2)
N5—C11	1.3928 (15)	C15—H15	0.9500
N6—C16	1.3368 (17)	C16—H16	0.9500
N6—C12	1.3539 (15)	C18—C19	1.3527 (19)
N7—C17	1.3503 (17)	C18—H18	0.9500
N7—H7A	0.88 (2)	C19—C20	1.4731 (17)
N7—H7B	0.86 (2)	C20—C21	1.3984 (18)
N8—C17	1.3102 (17)	C21—C22	1.3848 (19)
N8—C19	1.3915 (15)	C21—H21	0.9500
N9—C24	1.3402 (18)	C22—C23	1.3796 (19)
N9—C20	1.3451 (16)	C22—H22	0.9500
C2—C3	1.3553 (18)	C23—C24	1.383 (2)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.4712 (17)	C24—H24	0.9500
N2···C23^i	3.396 (2)	C6···C11^iii	3.276 (2)
C1···C23^i	3.367 (2)	N3···C22^ii	3.4973 (17)
C2···C20^ii	3.3936 (16)	N3···C23^ii	3.3729 (18)
C2···C21^ii	3.346 (2)	C14···N8^iv	3.2414 (16)
C5···C9^iii	3.489 (2)	C14···C19^iv	3.4051 (16)
C6···N5^iii	3.2952 (19)
C2—S1—C1	89.27 (6)	C11—C10—S2	110.28 (9)
C10—S2—C9	89.04 (6)	C11—C10—H10	124.9
C18—S3—C17	89.04 (6)	S2—C10—H10	124.9
C1—N1—H1A	118.1 (13)	C10—C11—N5	115.91 (11)
C1—N1—H1B	121.9 (12)	C10—C11—C12	124.46 (11)
H1A—N1—H1B	120.0 (17)	N5—C11—C12	119.63 (10)
C1—N2—C3	110.46 (11)	N6—C12—C13	121.81 (11)
C8—N3—C4	116.74 (12)	N6—C12—C11	116.97 (11)
C9—N4—H4A	116.1 (11)	C13—C12—C11	121.21 (11)
C9—N4—H4B	121.0 (12)	C14—C13—C12	119.24 (12)
H4A—N4—H4B	121.3 (16)	C14—C13—H13	120.4
C9—N5—C11	110.33 (10)	C12—C13—H13	120.4
C16—N6—C12	117.60 (11)	C13—C14—C15	119.35 (12)
C17—N7—H7A	115.1 (13)	C13—C14—H14	120.3
C17—N7—H7B	119.5 (13)	C15—C14—H14	120.3
H7A—N7—H7B	122.0 (18)	C14—C15—C16	117.71 (12)
C17—N8—C19	110.18 (11)	C14—C15—H15	121.1
C24—N9—C20	117.41 (12)	C16—C15—H15	121.1
N2—C1—N1	124.34 (12)	N6—C16—C15	124.27 (12)
N2—C1—S1	114.13 (9)	N6—C16—H16	117.9
N1—C1—S1	121.49 (11)	C15—C16—H16	117.9
C3—C2—S1	109.89 (9)	N8—C17—N7	124.31 (13)
C3—C2—H2	125.1	N8—C17—S3	114.53 (9)
S1—C2—H2	125.1	N7—C17—S3	121.16 (11)
C2—C3—N2	116.24 (11)	C19—C18—S3	110.02 (9)
C2—C3—C4	124.86 (11)	C19—C18—H18	125.0
N2—C3—C4	118.66 (11)	S3—C18—H18	125.0
N3—C4—C5	122.80 (12)	C18—C19—N8	116.22 (11)
N3—C4—C3	116.92 (12)	C18—C19—C20	124.60 (11)
C5—C4—C3	120.23 (11)	N8—C19—C20	119.03 (11)
C6—C5—C4	119.09 (12)	N9—C20—C21	122.06 (12)
C6—C5—H5	120.5	N9—C20—C19	116.56 (11)
C4—C5—H5	120.5	C21—C20—C19	121.27 (11)
C7—C6—C5	118.42 (13)	C22—C21—C20	119.18 (12)
C7—C6—H6	120.8	C22—C21—H21	120.4
C5—C6—H6	120.8	C20—C21—H21	120.4
C8—C7—C6	118.63 (13)	C23—C22—C21	119.05 (13)
C8—C7—H7	120.7	C23—C22—H22	120.5
C6—C7—H7	120.7	C21—C22—H22	120.5
N3—C8—C7	124.23 (12)	C22—C23—C24	118.14 (13)
N3—C8—H8	117.9	C22—C23—H23	120.9
C7—C8—H8	117.9	C24—C23—H23	120.9
N5—C9—N4	124.81 (11)	N9—C24—C23	124.16 (13)
N5—C9—S2	114.43 (9)	N9—C24—H24	117.9
N4—C9—S2	120.74 (10)	C23—C24—H24	117.9
C3—N2—C1—N1	177.16 (13)	C10—C11—C12—N6	13.75 (19)
C3—N2—C1—S1	−0.65 (14)	N5—C11—C12—N6	−166.42 (11)
C2—S1—C1—N2	0.64 (11)	C10—C11—C12—C13	−165.17 (12)
C2—S1—C1—N1	−177.24 (12)	N5—C11—C12—C13	14.66 (18)
C1—S1—C2—C3	−0.43 (10)	N6—C12—C13—C14	0.72 (19)
S1—C2—C3—N2	0.17 (15)	C11—C12—C13—C14	179.58 (12)
S1—C2—C3—C4	−174.06 (10)	C12—C13—C14—C15	−0.5 (2)
C1—N2—C3—C2	0.31 (16)	C13—C14—C15—C16	−0.4 (2)
C1—N2—C3—C4	174.91 (11)	C12—N6—C16—C15	−1.1 (2)
C8—N3—C4—C5	−3.09 (17)	C14—C15—C16—N6	1.3 (2)
C8—N3—C4—C3	174.21 (11)	C19—N8—C17—N7	−179.07 (12)
C2—C3—C4—N3	−22.76 (18)	C19—N8—C17—S3	0.64 (13)
N2—C3—C4—N3	163.14 (11)	C18—S3—C17—N8	−0.83 (10)
C2—C3—C4—C5	154.61 (12)	C18—S3—C17—N7	178.88 (12)
N2—C3—C4—C5	−19.49 (16)	C17—S3—C18—C19	0.76 (10)
N3—C4—C5—C6	1.13 (18)	S3—C18—C19—N8	−0.60 (14)
C3—C4—C5—C6	−176.08 (11)	S3—C18—C19—C20	175.01 (9)
C4—C5—C6—C7	1.68 (18)	C17—N8—C19—C18	−0.02 (15)
C5—C6—C7—C8	−2.39 (19)	C17—N8—C19—C20	−175.89 (10)
C4—N3—C8—C7	2.3 (2)	C24—N9—C20—C21	1.26 (19)
C6—C7—C8—N3	0.4 (2)	C24—N9—C20—C19	−175.00 (12)
C11—N5—C9—N4	−178.36 (13)	C18—C19—C20—N9	20.20 (17)
C11—N5—C9—S2	0.27 (14)	N8—C19—C20—N9	−164.30 (11)
C10—S2—C9—N5	−0.07 (11)	C18—C19—C20—C21	−156.09 (12)
C10—S2—C9—N4	178.62 (12)	N8—C19—C20—C21	19.41 (17)
C9—S2—C10—C11	−0.16 (10)	N9—C20—C21—C22	−0.83 (19)
S2—C10—C11—N5	0.35 (15)	C19—C20—C21—C22	175.26 (11)
S2—C10—C11—C12	−179.81 (10)	C20—C21—C22—C23	−0.20 (19)
C9—N5—C11—C10	−0.41 (16)	C21—C22—C23—C24	0.7 (2)
C9—N5—C11—C12	179.75 (11)	C20—N9—C24—C23	−0.7 (2)
C16—N6—C12—C13	0.04 (19)	C22—C23—C24—N9	−0.3 (2)
C16—N6—C12—C11	−178.86 (12)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N5	0.90 (2)	2.33 (2)	3.1852 (17)	159.1 (18)
N1—H1B···N9^iv	0.82 (2)	2.19 (2)	3.0077 (19)	170.1 (17)
N4—H4A···N2	0.889 (18)	2.101 (18)	2.9893 (17)	177.0 (15)
N4—H4B···N6^v	0.838 (19)	2.207 (19)	3.0320 (18)	168.1 (18)
N7—H7A···N8^i	0.88 (2)	2.21 (2)	3.0828 (19)	172.2 (19)
N7—H7B···N3	0.86 (2)	2.38 (2)	3.2249 (19)	169.1 (17)

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