Crystal structures of 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(3-nitro­phen­yl)acetamide monohydrate and N-(2-chloro­phen­yl)-2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]acetamide

In the title 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]acetamides, both compounds have a folded conformation about the methyl­ene C atom of the thio­acetamide bridge, with the pyrimidine ring being inclined to the benzene ring by 56.18 (6) and 67.84 (6)°. In both mol­ecules, there is an intra­molecular N—H...N hydrogen bond stabilizing the folded conformation.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.027
• wR factor = 0.069
• Data-to-parameter ratio = 14.3

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.099
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    --  H1WB   ...     Please Check

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1WB   ..  O3      ..       2.64 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         78 %

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2B    ...     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O1      ..       2.64 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(3-nitrophenyl)acetamide monohydrate

Crystal data

C12H12N6O3S·H2O	Dx = 1.537 Mg m^−3
Mr = 338.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 3265 reflections
a = 7.2326 (1) Å	θ = 2.0–28.3°
b = 14.3442 (2) Å	µ = 0.25 mm^−1
c = 14.0940 (3) Å	T = 293 K
V = 1462.19 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 704

Data collection

Bruker SMART APEXII area-detector diffractometer	3034 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.021
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 28.3°, θmin = 2.0°
Tmin = 0.785, Tmax = 0.845	h = −5→9
7912 measured reflections	k = −18→19
3265 independent reflections	l = −15→18

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 0.1263P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
3265 reflections	Δρmin = −0.17 e Å^−3
229 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0039 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 1217 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.07 (3)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	0.12955 (8)	0.37215 (3)	0.66439 (4)	0.03810 (14)
O1	0.2112 (3)	0.32497 (11)	0.42274 (13)	0.0555 (5)
O2	0.4515 (3)	0.40381 (12)	0.13791 (14)	0.0570 (5)
O3	0.4586 (3)	0.53670 (14)	0.06709 (14)	0.0602 (5)
N1	−0.0426 (3)	0.69929 (14)	0.58998 (15)	0.0483 (5)
H1A	−0.112 (3)	0.6759 (19)	0.550 (2)	0.039 (7)*
H1B	−0.049 (4)	0.7564 (18)	0.601 (2)	0.048 (7)*
N2	0.2912 (3)	0.62828 (15)	0.87403 (16)	0.0473 (5)
H2A	0.343 (4)	0.587 (2)	0.902 (2)	0.052 (9)*
H2B	0.303 (4)	0.683 (2)	0.891 (2)	0.058 (8)*
N3	0.2016 (2)	0.51355 (12)	0.77054 (12)	0.0346 (4)
N4	0.0368 (2)	0.54948 (11)	0.62840 (12)	0.0327 (4)
N5	0.1324 (3)	0.47612 (12)	0.44843 (13)	0.0361 (4)
H5	0.081 (4)	0.5115 (19)	0.490 (2)	0.050 (7)*
N6	0.4308 (3)	0.48792 (13)	0.13678 (13)	0.0404 (4)
C1	0.0378 (3)	0.64158 (12)	0.65303 (16)	0.0351 (4)
C2	0.1209 (3)	0.67214 (15)	0.73550 (15)	0.0386 (5)
H2	0.1206	0.7349	0.7522	0.046*
C3	0.2048 (3)	0.60567 (14)	0.79264 (17)	0.0359 (4)
C4	0.1191 (3)	0.49297 (13)	0.68900 (14)	0.0318 (4)
C5	0.0093 (3)	0.36034 (14)	0.55277 (16)	0.0369 (5)
H5A	−0.0345	0.2967	0.5466	0.044*
H5B	−0.0979	0.4010	0.5532	0.044*
C6	0.1278 (3)	0.38380 (14)	0.46763 (15)	0.0350 (4)
C7	0.2255 (3)	0.52300 (13)	0.37571 (15)	0.0327 (4)
C8	0.2440 (4)	0.61934 (14)	0.38488 (18)	0.0418 (5)
H8	0.2021	0.6488	0.4396	0.050*
C9	0.3239 (4)	0.67138 (15)	0.31366 (19)	0.0471 (6)
H9	0.3368	0.7355	0.3211	0.057*
C10	0.3850 (3)	0.62925 (15)	0.23135 (18)	0.0418 (5)
H10	0.4364	0.6640	0.1823	0.050*
C11	0.3670 (3)	0.53390 (15)	0.22449 (15)	0.0339 (4)
C12	0.2907 (3)	0.47907 (13)	0.29473 (15)	0.0331 (4)
H12	0.2832	0.4147	0.2880	0.040*
O1W	0.7494 (3)	0.61566 (15)	0.42859 (15)	0.0615 (5)
H1WA	0.7637	0.5885	0.3748	0.092*
H1WB	0.6377	0.6003	0.4521	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0581 (3)	0.0259 (2)	0.0302 (2)	−0.00098 (19)	−0.0040 (2)	0.0025 (2)
O1	0.0851 (13)	0.0319 (8)	0.0494 (11)	0.0075 (8)	0.0205 (9)	−0.0010 (7)
O2	0.0763 (12)	0.0476 (9)	0.0470 (11)	0.0082 (9)	0.0072 (9)	−0.0122 (8)
O3	0.0765 (12)	0.0711 (12)	0.0328 (9)	−0.0071 (10)	0.0107 (9)	0.0022 (9)
N1	0.0692 (15)	0.0309 (9)	0.0448 (12)	0.0072 (9)	−0.0120 (11)	−0.0024 (8)
N2	0.0644 (14)	0.0385 (11)	0.0390 (12)	−0.0024 (10)	−0.0091 (10)	−0.0079 (9)
N3	0.0424 (9)	0.0331 (8)	0.0283 (9)	−0.0021 (7)	0.0003 (7)	−0.0017 (7)
N4	0.0427 (9)	0.0278 (7)	0.0278 (8)	−0.0008 (7)	0.0018 (7)	−0.0007 (6)
N5	0.0507 (11)	0.0288 (8)	0.0287 (9)	0.0018 (7)	0.0073 (8)	−0.0020 (7)
N6	0.0394 (9)	0.0484 (10)	0.0336 (10)	−0.0015 (8)	−0.0007 (8)	−0.0030 (8)
C1	0.0408 (10)	0.0297 (8)	0.0349 (11)	0.0008 (7)	0.0066 (9)	−0.0008 (8)
C2	0.0517 (13)	0.0281 (9)	0.0360 (11)	−0.0036 (9)	0.0036 (10)	−0.0058 (8)
C3	0.0396 (10)	0.0362 (9)	0.0320 (11)	−0.0049 (9)	0.0062 (8)	−0.0038 (8)
C4	0.0378 (10)	0.0285 (9)	0.0290 (11)	−0.0033 (8)	0.0059 (8)	−0.0007 (7)
C5	0.0467 (11)	0.0319 (10)	0.0322 (11)	−0.0077 (8)	−0.0008 (9)	−0.0009 (8)
C6	0.0446 (12)	0.0303 (9)	0.0302 (11)	−0.0013 (8)	−0.0024 (9)	−0.0007 (7)
C7	0.0395 (11)	0.0295 (9)	0.0292 (10)	−0.0005 (8)	−0.0003 (8)	0.0008 (8)
C8	0.0561 (13)	0.0317 (10)	0.0376 (12)	0.0005 (9)	0.0074 (10)	−0.0035 (9)
C9	0.0664 (15)	0.0280 (9)	0.0469 (13)	−0.0015 (10)	0.0084 (12)	0.0025 (9)
C10	0.0500 (13)	0.0350 (11)	0.0404 (13)	−0.0008 (9)	0.0078 (11)	0.0076 (9)
C11	0.0360 (10)	0.0369 (10)	0.0288 (10)	0.0026 (9)	−0.0001 (8)	−0.0002 (8)
C12	0.0380 (10)	0.0301 (8)	0.0311 (10)	−0.0006 (8)	−0.0011 (8)	−0.0003 (8)
O1W	0.0706 (12)	0.0695 (12)	0.0444 (11)	−0.0050 (9)	−0.0003 (10)	−0.0118 (9)

Geometric parameters (Å, º)

S1—C4	1.769 (2)	C1—C2	1.380 (3)
S1—C5	1.805 (2)	C2—C3	1.388 (3)
O1—C6	1.215 (3)	C2—H2	0.9300
O2—N6	1.216 (2)	C5—C6	1.512 (3)
O3—N6	1.223 (3)	C5—H5A	0.9700
N1—C1	1.347 (3)	C5—H5B	0.9700
N1—H1A	0.83 (3)	C7—C12	1.386 (3)
N1—H1B	0.84 (3)	C7—C8	1.394 (3)
N2—C3	1.346 (3)	C8—C9	1.378 (3)
N2—H2A	0.80 (3)	C8—H8	0.9300
N2—H2B	0.83 (3)	C9—C10	1.381 (3)
N3—C4	1.328 (3)	C9—H9	0.9300
N3—C3	1.358 (3)	C10—C11	1.377 (3)
N4—C4	1.319 (3)	C10—H10	0.9300
N4—C1	1.366 (2)	C11—C12	1.380 (3)
N5—C6	1.352 (3)	C12—H12	0.9300
N5—C7	1.398 (3)	O1W—H1WA	0.8582
N5—H5	0.86 (3)	O1W—H1WB	0.9004
N6—C11	1.475 (3)
C4—S1—C5	104.01 (9)	C6—C5—H5A	108.9
C1—N1—H1A	117.8 (18)	S1—C5—H5A	108.9
C1—N1—H1B	120 (2)	C6—C5—H5B	108.9
H1A—N1—H1B	120 (3)	S1—C5—H5B	108.9
C3—N2—H2A	117 (2)	H5A—C5—H5B	107.7
C3—N2—H2B	121 (2)	O1—C6—N5	124.3 (2)
H2A—N2—H2B	121 (3)	O1—C6—C5	122.68 (19)
C4—N3—C3	114.97 (18)	N5—C6—C5	113.01 (18)
C4—N4—C1	115.30 (18)	C12—C7—C8	119.6 (2)
C6—N5—C7	129.02 (18)	C12—C7—N5	123.27 (17)
C6—N5—H5	115.5 (19)	C8—C7—N5	117.05 (19)
C7—N5—H5	115.1 (19)	C9—C8—C7	120.6 (2)
O2—N6—O3	123.9 (2)	C9—C8—H8	119.7
O2—N6—C11	118.11 (18)	C7—C8—H8	119.7
O3—N6—C11	117.96 (18)	C8—C9—C10	120.6 (2)
N1—C1—N4	115.1 (2)	C8—C9—H9	119.7
N1—C1—C2	123.28 (19)	C10—C9—H9	119.7
N4—C1—C2	121.57 (19)	C11—C10—C9	117.6 (2)
C1—C2—C3	117.44 (19)	C11—C10—H10	121.2
C1—C2—H2	121.3	C9—C10—H10	121.2
C3—C2—H2	121.3	C10—C11—C12	123.6 (2)
N2—C3—N3	116.0 (2)	C10—C11—N6	118.26 (19)
N2—C3—C2	122.1 (2)	C12—C11—N6	118.14 (18)
N3—C3—C2	121.9 (2)	C11—C12—C7	117.89 (17)
N4—C4—N3	128.79 (18)	C11—C12—H12	121.1
N4—C4—S1	119.62 (15)	C7—C12—H12	121.1
N3—C4—S1	111.59 (15)	H1WA—O1W—H1WB	108.8
C6—C5—S1	113.43 (15)
C4—N4—C1—N1	178.57 (19)	S1—C5—C6—N5	−84.2 (2)
C4—N4—C1—C2	0.5 (3)	C6—N5—C7—C12	18.1 (3)
N1—C1—C2—C3	−177.6 (2)	C6—N5—C7—C8	−164.9 (2)
N4—C1—C2—C3	0.3 (3)	C12—C7—C8—C9	1.0 (4)
C4—N3—C3—N2	−178.7 (2)	N5—C7—C8—C9	−176.0 (2)
C4—N3—C3—C2	2.5 (3)	C7—C8—C9—C10	0.8 (4)
C1—C2—C3—N2	179.3 (2)	C8—C9—C10—C11	−1.5 (4)
C1—C2—C3—N3	−1.9 (3)	C9—C10—C11—C12	0.5 (3)
C1—N4—C4—N3	0.3 (3)	C9—C10—C11—N6	179.7 (2)
C1—N4—C4—S1	−179.23 (14)	O2—N6—C11—C10	164.8 (2)
C3—N3—C4—N4	−1.7 (3)	O3—N6—C11—C10	−15.6 (3)
C3—N3—C4—S1	177.82 (16)	O2—N6—C11—C12	−15.9 (3)
C5—S1—C4—N4	−0.85 (19)	O3—N6—C11—C12	163.6 (2)
C5—S1—C4—N3	179.56 (14)	C10—C11—C12—C7	1.3 (3)
C4—S1—C5—C6	81.31 (16)	N6—C11—C12—C7	−177.94 (17)
C7—N5—C6—O1	1.4 (4)	C8—C7—C12—C11	−2.0 (3)
C7—N5—C6—C5	−179.6 (2)	N5—C7—C12—C11	174.86 (19)
S1—C5—C6—O1	94.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N4	0.86 (3)	2.05 (3)	2.832 (3)	151 (3)
C12—H12···O1	0.93	2.35	2.911 (3)	118
N1—H1A···O1W^i	0.83 (3)	2.16 (3)	2.979 (3)	170 (2)
N1—H1B···O2^ii	0.84 (3)	2.29 (3)	3.082 (3)	159 (3)
N2—H2A···O3^iii	0.80 (3)	2.58 (3)	3.255 (3)	143 (3)
N2—H2B···O1^ii	0.83 (3)	2.09 (3)	2.904 (3)	170 (3)
O1W—H1WA···N3^iv	0.86	2.09	2.919 (3)	162
O1W—H1WB···O3^v	0.90	2.64	3.294 (3)	130

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

(II) N-(2-Chlorophenyl)-2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamide

Crystal data

C12H12ClN5OS	Z = 2
Mr = 309.78	F(000) = 320
Triclinic, P1	Dx = 1.487 Mg m^−3
a = 7.2528 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6249 (3) Å	Cell parameters from 2822 reflections
c = 13.0649 (4) Å	θ = 1.6–26.4°
α = 91.410 (2)°	µ = 0.43 mm^−1
β = 105.924 (2)°	T = 293 K
γ = 94.647 (2)°	Block, colourless
V = 691.68 (4) Å^3	0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer	2519 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.022
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.4°, θmin = 1.6°
Tmin = 0.785, Tmax = 0.845	h = −9→8
10154 measured reflections	k = −9→9
2822 independent reflections	l = −16→16

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)] = 0.035	Hydrogen site location: mixed
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.2692P] where P = (Fo^2 + 2Fc^2)/3
2822 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Cl1	−0.32045 (7)	0.83502 (8)	0.11080 (5)	0.06488 (18)
S1	0.22688 (6)	0.44103 (6)	0.41282 (3)	0.04714 (15)
O1	0.35760 (17)	0.81194 (17)	0.26781 (10)	0.0503 (3)
N1	−0.2505 (3)	−0.0531 (2)	0.40354 (14)	0.0541 (4)
H1A	−0.163 (3)	−0.091 (3)	0.4537 (18)	0.051 (6)*
H1B	−0.361 (3)	−0.101 (3)	0.3829 (18)	0.058 (6)*
N2	−0.4671 (2)	0.4665 (2)	0.23211 (16)	0.0576 (5)
H2A	−0.437 (3)	0.572 (3)	0.2321 (18)	0.062 (7)*
H2B	−0.584 (4)	0.428 (3)	0.2221 (19)	0.070 (7)*
N3	−0.03937 (19)	0.19020 (19)	0.40540 (10)	0.0396 (3)
N4	−0.14840 (18)	0.44884 (18)	0.31711 (10)	0.0371 (3)
N5	0.0527 (2)	0.6847 (2)	0.20471 (11)	0.0416 (3)
H5	−0.040 (3)	0.631 (3)	0.2233 (15)	0.045 (5)*
C1	−0.2221 (2)	0.1113 (2)	0.37325 (12)	0.0383 (3)
C2	−0.3723 (2)	0.1992 (2)	0.31353 (13)	0.0403 (4)
H2	−0.4970	0.1447	0.2910	0.048*
C3	−0.3310 (2)	0.3694 (2)	0.28860 (13)	0.0378 (3)
C4	−0.0176 (2)	0.3525 (2)	0.37342 (11)	0.0353 (3)
C5	0.2110 (3)	0.6742 (2)	0.39173 (13)	0.0453 (4)
H5A	0.0924	0.7068	0.4045	0.054*
H5B	0.3169	0.7396	0.4442	0.054*
C6	0.2155 (2)	0.7302 (2)	0.28193 (12)	0.0359 (3)
C7	0.0187 (2)	0.7245 (2)	0.09613 (12)	0.0375 (3)
C8	−0.1521 (2)	0.7917 (2)	0.04306 (14)	0.0428 (4)
C9	−0.1897 (3)	0.8314 (3)	−0.06301 (15)	0.0545 (5)
H9	−0.3048	0.8763	−0.0976	0.065*
C10	−0.0557 (4)	0.8039 (3)	−0.11667 (15)	0.0603 (6)
H10	−0.0795	0.8312	−0.1879	0.072*
C11	0.1148 (3)	0.7360 (3)	−0.06546 (15)	0.0556 (5)
H11	0.2048	0.7168	−0.1024	0.067*
C12	0.1516 (3)	0.6965 (2)	0.04065 (14)	0.0454 (4)
H12	0.2665	0.6508	0.0748	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0473 (3)	0.0730 (4)	0.0803 (4)	0.0106 (2)	0.0244 (2)	0.0255 (3)
S1	0.0309 (2)	0.0609 (3)	0.0435 (2)	−0.00578 (18)	0.00128 (17)	0.0193 (2)
O1	0.0404 (6)	0.0548 (7)	0.0492 (7)	−0.0158 (5)	0.0072 (5)	0.0071 (6)
N1	0.0440 (9)	0.0474 (9)	0.0579 (10)	−0.0079 (7)	−0.0061 (8)	0.0187 (7)
N2	0.0319 (8)	0.0501 (10)	0.0858 (13)	0.0021 (7)	0.0066 (8)	0.0271 (9)
N3	0.0339 (7)	0.0466 (8)	0.0349 (7)	−0.0005 (6)	0.0043 (5)	0.0105 (6)
N4	0.0318 (6)	0.0431 (7)	0.0360 (7)	−0.0010 (5)	0.0094 (5)	0.0082 (5)
N5	0.0339 (7)	0.0515 (8)	0.0360 (7)	−0.0097 (6)	0.0072 (6)	0.0099 (6)
C1	0.0388 (8)	0.0418 (8)	0.0307 (7)	−0.0015 (7)	0.0052 (6)	0.0049 (6)
C2	0.0314 (8)	0.0458 (9)	0.0390 (8)	−0.0034 (6)	0.0037 (6)	0.0068 (7)
C3	0.0322 (8)	0.0447 (9)	0.0364 (8)	0.0017 (6)	0.0097 (6)	0.0070 (6)
C4	0.0315 (7)	0.0469 (9)	0.0262 (7)	−0.0018 (6)	0.0073 (6)	0.0049 (6)
C5	0.0447 (9)	0.0511 (10)	0.0343 (8)	−0.0120 (7)	0.0062 (7)	−0.0025 (7)
C6	0.0355 (8)	0.0324 (7)	0.0376 (8)	−0.0031 (6)	0.0082 (6)	0.0013 (6)
C7	0.0398 (8)	0.0337 (8)	0.0350 (8)	−0.0089 (6)	0.0069 (6)	0.0043 (6)
C8	0.0405 (9)	0.0384 (8)	0.0446 (9)	−0.0071 (7)	0.0061 (7)	0.0053 (7)
C9	0.0582 (11)	0.0472 (10)	0.0447 (10)	−0.0083 (8)	−0.0049 (8)	0.0103 (8)
C10	0.0873 (15)	0.0526 (11)	0.0325 (9)	−0.0121 (10)	0.0073 (9)	0.0031 (8)
C11	0.0761 (14)	0.0496 (10)	0.0447 (10)	−0.0064 (9)	0.0269 (10)	−0.0024 (8)
C12	0.0486 (10)	0.0421 (9)	0.0456 (9)	−0.0015 (7)	0.0145 (8)	0.0029 (7)

Geometric parameters (Å, º)

Cl1—C8	1.7397 (19)	C1—C2	1.386 (2)
S1—C4	1.7753 (15)	C2—C3	1.375 (2)
S1—C5	1.8135 (19)	C2—H2	0.9300
O1—C6	1.2207 (19)	C5—C6	1.515 (2)
N1—C1	1.340 (2)	C5—H5A	0.9700
N1—H1A	0.85 (2)	C5—H5B	0.9700
N1—H1B	0.83 (2)	C7—C12	1.382 (2)
N2—C3	1.346 (2)	C7—C8	1.388 (2)
N2—H2A	0.81 (3)	C8—C9	1.383 (3)
N2—H2B	0.85 (3)	C9—C10	1.371 (3)
N3—C4	1.327 (2)	C9—H9	0.9300
N3—C1	1.359 (2)	C10—C11	1.382 (3)
N4—C4	1.318 (2)	C10—H10	0.9300
N4—C3	1.360 (2)	C11—C12	1.384 (3)
N5—C6	1.340 (2)	C11—H11	0.9300
N5—C7	1.417 (2)	C12—H12	0.9300
N5—H5	0.85 (2)
C4—S1—C5	103.22 (8)	S1—C5—H5A	108.5
C1—N1—H1A	118.4 (15)	C6—C5—H5B	108.5
C1—N1—H1B	116.7 (16)	S1—C5—H5B	108.5
H1A—N1—H1B	123 (2)	H5A—C5—H5B	107.5
C3—N2—H2A	116.6 (17)	O1—C6—N5	124.20 (15)
C3—N2—H2B	118.0 (17)	O1—C6—C5	121.24 (15)
H2A—N2—H2B	120 (2)	N5—C6—C5	114.56 (14)
C4—N3—C1	115.11 (13)	C12—C7—C8	118.68 (15)
C4—N4—C3	114.72 (13)	C12—C7—N5	121.45 (15)
C6—N5—C7	125.63 (14)	C8—C7—N5	119.87 (15)
C6—N5—H5	116.8 (13)	C9—C8—C7	121.22 (18)
C7—N5—H5	117.5 (13)	C9—C8—Cl1	118.54 (15)
N1—C1—N3	117.08 (15)	C7—C8—Cl1	120.20 (13)
N1—C1—C2	121.83 (15)	C10—C9—C8	119.36 (19)
N3—C1—C2	121.08 (14)	C10—C9—H9	120.3
C3—C2—C1	117.94 (14)	C8—C9—H9	120.3
C3—C2—H2	121.0	C9—C10—C11	120.31 (17)
C1—C2—H2	121.0	C9—C10—H10	119.8
N2—C3—N4	115.59 (15)	C11—C10—H10	119.8
N2—C3—C2	122.48 (15)	C10—C11—C12	120.09 (19)
N4—C3—C2	121.90 (15)	C10—C11—H11	120.0
N4—C4—N3	129.18 (14)	C12—C11—H11	120.0
N4—C4—S1	118.71 (12)	C7—C12—C11	120.34 (18)
N3—C4—S1	112.10 (11)	C7—C12—H12	119.8
C6—C5—S1	115.29 (12)	C11—C12—H12	119.8
C6—C5—H5A	108.5
C4—N3—C1—N1	179.80 (16)	C7—N5—C6—C5	178.60 (16)
C4—N3—C1—C2	−1.4 (2)	S1—C5—C6—O1	−106.66 (16)
N1—C1—C2—C3	178.13 (17)	S1—C5—C6—N5	74.10 (18)
N3—C1—C2—C3	−0.6 (3)	C6—N5—C7—C12	47.4 (2)
C4—N4—C3—N2	179.24 (16)	C6—N5—C7—C8	−133.27 (18)
C4—N4—C3—C2	−2.5 (2)	C12—C7—C8—C9	−0.5 (2)
C1—C2—C3—N2	−179.19 (18)	N5—C7—C8—C9	−179.80 (15)
C1—C2—C3—N4	2.7 (3)	C12—C7—C8—Cl1	−178.14 (12)
C3—N4—C4—N3	0.3 (2)	N5—C7—C8—Cl1	2.5 (2)
C3—N4—C4—S1	178.72 (11)	C7—C8—C9—C10	0.0 (3)
C1—N3—C4—N4	1.7 (2)	Cl1—C8—C9—C10	177.71 (14)
C1—N3—C4—S1	−176.86 (11)	C8—C9—C10—C11	0.5 (3)
C5—S1—C4—N4	15.56 (15)	C9—C10—C11—C12	−0.5 (3)
C5—S1—C4—N3	−165.73 (12)	C8—C7—C12—C11	0.5 (2)
C4—S1—C5—C6	−89.86 (13)	N5—C7—C12—C11	179.79 (15)
C7—N5—C6—O1	−0.6 (3)	C10—C11—C12—C7	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N4	0.85 (2)	2.12 (2)	2.898 (2)	152 (2)
N2—H2A···Cl1	0.81 (3)	2.81 (2)	3.493 (2)	143 (2)
N1—H1A···N3^i	0.85 (2)	2.21 (2)	3.058 (2)	174 (2)
N1—H1B···O1^ii	0.83 (2)	2.21 (2)	2.992 (2)	157 (2)
N2—H2A···O1^iii	0.81 (3)	2.56 (2)	3.095 (2)	124 (2)
C2—H2···O1^ii	0.93	2.64	3.353 (2)	134

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