N⁶-Substituted 2-amino-4-chloro-5-formylpyrimidines: puckered versus planar pyrimidine rings, and hydrogen-bonded aggregation in zero, one, two and three dimensions

The structures of 12 new N⁶-substituted 2-amino-4-chloro-5-formylpyrimidines, where the N⁶ substituent is of the type NHR or NR¹R², have been determined. The intramolecular dimensions provide strong evidence for the development of polarized, charge-separated molecular-electronic structures, with the positive charge delocalized over the two exocyclic amino N atoms and with negative charge on the formyl O atom. This polarization appears to be independent of the significant puckering, in seven of the compounds, of the pyrimidine rings from planarity towards boat, twist-boat or screw-boat conformations. In 11 of the compounds studied here, N—H...N hydrogen bonds link pairs of molecules into centrosymmetric dimer units, and their overall crystal structures are determined by the patterns of hydrogen bonds by which these units are further linked. Examples are reported in which no further hydrogen bonding occurs; in which the dimers are linked into chains of rings, or into sheets; and in which sheets are formed by the π-stacking of hydrogen-bonded chains of rings. In the sole structure lacking the dimer motif, N—H...O and N—H...N hydrogen bonds cooperate to generate a three-dimensional framework structure.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: Sir2004 (Burla et al., 2005). Program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX), (X); OSCAIL (McArdle, 2003) & SHELXL97 (Sheldrick, 1997) for (VI), (XI), (XII). For all compounds, molecular graphics: PLATON (Spek, 2003). Software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX), (X); SHELXL97 & PRPKAPPA (Ferguson, 1999) for (VI), (XI), (XII).

Figures

In full text version

(I)

Crystal data

C11H15ClN4O	Z = 2
Mr = 254.72	F(000) = 268
Triclinic, P1	Dx = 1.382 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.907 (2) Å	Cell parameters from 2807 reflections
b = 10.398 (3) Å	θ = 3.4–27.5°
c = 10.801 (2) Å	µ = 0.30 mm^−1
α = 110.86 (3)°	T = 120 K
β = 94.19 (2)°	Plate, colourless
γ = 96.00 (3)°	0.48 × 0.28 × 0.08 mm
V = 612.2 (3) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2807 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2278 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ϕ & ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −7→7
Tmin = 0.869, Tmax = 0.976	k = −13→13
16678 measured reflections	l = −13→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 0.3635P] where P = (Fo^2 + 2Fc^2)/3
2807 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.56158 (7)	1.01124 (4)	0.74715 (4)	0.02841 (13)
O51	0.0293 (2)	0.66373 (13)	0.56409 (12)	0.0289 (3)
N1	0.5886 (2)	0.70091 (14)	0.34068 (14)	0.0226 (3)
N2	0.9231 (2)	0.83585 (15)	0.34262 (14)	0.0267 (3)
N3	0.7374 (2)	0.91037 (14)	0.52819 (13)	0.0214 (3)
N61	0.2491 (2)	0.57177 (14)	0.34223 (14)	0.0232 (3)
C2	0.7431 (3)	0.81334 (17)	0.40417 (16)	0.0211 (3)
C4	0.5594 (3)	0.88767 (16)	0.58716 (16)	0.0205 (3)
C5	0.3806 (3)	0.77795 (17)	0.53498 (16)	0.0209 (3)
C6	0.4079 (3)	0.68211 (16)	0.40452 (16)	0.0207 (3)
C51	0.1866 (3)	0.76130 (18)	0.60481 (17)	0.0250 (4)
C61	0.2650 (3)	0.46937 (17)	0.21055 (16)	0.0218 (3)
C62	0.4087 (3)	0.35948 (19)	0.22014 (18)	0.0285 (4)
C63	0.4210 (3)	0.2515 (2)	0.0818 (2)	0.0332 (4)
C64	0.1811 (3)	0.18498 (19)	0.01160 (19)	0.0334 (4)
C65	0.0392 (3)	0.2959 (2)	0.00314 (18)	0.0313 (4)
C66	0.0247 (3)	0.40317 (18)	0.14136 (17)	0.0249 (4)
H2A	0.9351	0.7766	0.2648	0.032*
H2B	1.0214	0.9093	0.3812	0.032*
H61	0.1440	0.5598	0.3897	0.028*
H51	0.1801	0.8316	0.6892	0.030*
H61A	0.3402	0.5183	0.1565	0.026*
H62A	0.3405	0.3129	0.2769	0.034*
H62B	0.5654	0.4044	0.2624	0.034*
H63A	0.5018	0.2966	0.0276	0.040*
H63B	0.5093	0.1787	0.0906	0.040*
H64A	0.1921	0.1188	−0.0794	0.040*
H64B	0.1053	0.1326	0.0614	0.040*
H65A	−0.1173	0.2516	−0.0402	0.038*
H65B	0.1091	0.3432	−0.0527	0.038*
H66A	−0.0641	0.4758	0.1328	0.030*
H66B	−0.0553	0.3576	0.1954	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0280 (2)	0.0250 (2)	0.0229 (2)	−0.00440 (16)	0.00387 (15)	−0.00040 (16)
O51	0.0227 (6)	0.0290 (7)	0.0308 (7)	−0.0057 (5)	0.0045 (5)	0.0084 (5)
N1	0.0187 (7)	0.0217 (7)	0.0230 (7)	−0.0046 (5)	0.0006 (5)	0.0053 (6)
N2	0.0224 (7)	0.0263 (7)	0.0226 (7)	−0.0085 (6)	0.0031 (5)	0.0018 (6)
N3	0.0197 (7)	0.0201 (7)	0.0210 (7)	−0.0031 (5)	−0.0005 (5)	0.0057 (5)
N61	0.0190 (7)	0.0221 (7)	0.0224 (7)	−0.0052 (5)	0.0027 (5)	0.0030 (6)
C2	0.0184 (8)	0.0217 (8)	0.0216 (8)	−0.0017 (6)	0.0001 (6)	0.0078 (6)
C4	0.0211 (8)	0.0191 (7)	0.0190 (7)	0.0010 (6)	−0.0005 (6)	0.0051 (6)
C5	0.0188 (8)	0.0208 (8)	0.0209 (8)	−0.0017 (6)	0.0004 (6)	0.0064 (6)
C6	0.0189 (8)	0.0197 (8)	0.0226 (8)	−0.0002 (6)	−0.0003 (6)	0.0079 (6)
C51	0.0235 (8)	0.0236 (8)	0.0248 (8)	0.0001 (7)	0.0034 (7)	0.0058 (7)
C61	0.0195 (8)	0.0209 (8)	0.0205 (8)	−0.0040 (6)	0.0018 (6)	0.0039 (6)
C62	0.0194 (8)	0.0324 (9)	0.0297 (9)	0.0021 (7)	0.0013 (7)	0.0072 (8)
C63	0.0289 (10)	0.0305 (10)	0.0365 (10)	0.0064 (8)	0.0099 (8)	0.0060 (8)
C64	0.0362 (10)	0.0242 (9)	0.0307 (10)	−0.0028 (8)	0.0092 (8)	0.0002 (7)
C65	0.0269 (9)	0.0332 (10)	0.0241 (9)	−0.0046 (7)	−0.0008 (7)	0.0020 (7)
C66	0.0196 (8)	0.0244 (8)	0.0239 (8)	−0.0008 (6)	−0.0020 (6)	0.0027 (7)

Geometric parameters (Å, º)

Cl4—C4	1.7461 (17)	C61—C66	1.523 (2)
O51—C51	1.229 (2)	C61—H61A	1.00
N1—C2	1.336 (2)	C62—C63	1.529 (3)
N1—C6	1.346 (2)	C62—H62A	0.99
N2—C2	1.338 (2)	C62—H62B	0.99
N2—H2A	0.86	C63—C64	1.525 (3)
N2—H2B	0.86	C63—H63A	0.99
N3—C4	1.311 (2)	C63—H63B	0.99
N3—C2	1.366 (2)	C64—C65	1.519 (3)
N61—C6	1.335 (2)	C64—H64A	0.99
N61—C61	1.459 (2)	C64—H64B	0.99
N61—H61	0.8597	C65—C66	1.527 (2)
C4—C5	1.392 (2)	C65—H65A	0.99
C5—C6	1.439 (2)	C65—H65B	0.99
C5—C51	1.446 (2)	C66—H66A	0.99
C51—H51	0.95	C66—H66B	0.99
C61—C62	1.520 (2)
C2—N1—C6	116.86 (14)	C61—C62—H62A	109.5
C2—N2—H2A	118.5	C63—C62—H62A	109.5
C2—N2—H2B	119.2	C61—C62—H62B	109.5
H2A—N2—H2B	122.2	C63—C62—H62B	109.5
C4—N3—C2	114.73 (14)	H62A—C62—H62B	108.1
C6—N61—C61	123.28 (14)	C64—C63—C62	110.69 (15)
C6—N61—H61	114.6	C64—C63—H63A	109.5
C61—N61—H61	121.7	C62—C63—H63A	109.5
N1—C2—N2	118.27 (15)	C64—C63—H63B	109.5
N1—C2—N3	126.44 (15)	C62—C63—H63B	109.5
N2—C2—N3	115.29 (14)	H63A—C63—H63B	108.1
N3—C4—C5	126.53 (15)	C65—C64—C63	110.28 (15)
N3—C4—Cl4	113.45 (12)	C65—C64—H64A	109.6
C5—C4—Cl4	120.02 (13)	C63—C64—H64A	109.6
C4—C5—C6	113.37 (15)	C65—C64—H64B	109.6
C4—C5—C51	123.47 (15)	C63—C64—H64B	109.6
C6—C5—C51	123.16 (14)	H64A—C64—H64B	108.1
N61—C6—N1	118.02 (15)	C64—C65—C66	111.32 (15)
N61—C6—C5	119.91 (14)	C64—C65—H65A	109.4
N1—C6—C5	122.06 (14)	C66—C65—H65A	109.4
O51—C51—C5	125.42 (16)	C64—C65—H65B	109.4
O51—C51—H51	117.3	C66—C65—H65B	109.4
C5—C51—H51	117.3	H65A—C65—H65B	108.0
N61—C61—C62	111.22 (14)	C61—C66—C65	109.85 (14)
N61—C61—C66	109.38 (13)	C61—C66—H66A	109.7
C62—C61—C66	110.89 (14)	C65—C66—H66A	109.7
N61—C61—H61A	108.4	C61—C66—H66B	109.7
C62—C61—H61A	108.4	C65—C66—H66B	109.7
C66—C61—H61A	108.4	H66A—C66—H66B	108.2
C61—C62—C63	110.78 (15)
C6—N1—C2—N2	−179.16 (15)	C51—C5—C6—N61	0.2 (2)
C6—N1—C2—N3	0.8 (2)	C4—C5—C6—N1	−1.1 (2)
C4—N3—C2—N1	−0.4 (2)	C51—C5—C6—N1	179.05 (15)
C4—N3—C2—N2	179.58 (14)	C4—C5—C51—O51	−177.51 (17)
C2—N3—C4—C5	−1.0 (2)	C6—C5—C51—O51	2.3 (3)
C2—N3—C4—Cl4	178.43 (11)	C6—N61—C61—C62	84.52 (19)
N3—C4—C5—C6	1.7 (2)	C6—N61—C61—C66	−152.66 (15)
Cl4—C4—C5—C6	−177.69 (11)	N61—C61—C62—C63	179.10 (14)
N3—C4—C5—C51	−178.52 (16)	C66—C61—C62—C63	57.15 (19)
Cl4—C4—C5—C51	2.1 (2)	C61—C62—C63—C64	−56.6 (2)
C61—N61—C6—N1	1.6 (2)	C62—C63—C64—C65	56.5 (2)
C61—N61—C6—C5	−179.52 (15)	C63—C64—C65—C66	−57.3 (2)
C2—N1—C6—N61	178.89 (14)	N61—C61—C66—C65	179.87 (14)
C2—N1—C6—C5	0.0 (2)	C62—C61—C66—C65	−57.11 (19)
C4—C5—C6—N61	−179.97 (15)	C64—C65—C66—C61	57.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3^i	0.86	2.11	2.966 (2)	179
N61—H61···O51	0.86	2.02	2.725 (2)	139

Symmetry code: (i) −x+2, −y+2, −z+1.

(II)

Crystal data

C9H13ClN4O	F(000) = 480
Mr = 228.68	Dx = 1.474 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2357 reflections
a = 11.328 (3) Å	θ = 4.4–27.5°
b = 8.0810 (4) Å	µ = 0.35 mm^−1
c = 11.3849 (12) Å	T = 120 K
β = 98.709 (14)°	Plate, colourless
V = 1030.2 (3) Å^3	0.37 × 0.36 × 0.08 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2357 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1408 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
ϕ & ω scans	θmax = 27.5°, θmin = 4.4°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −14→14
Tmin = 0.882, Tmax = 0.973	k = −10→10
21126 measured reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 1.3692P] where P = (Fo^2 + 2Fc^2)/3
2357 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.4610 (2)	0.3978 (3)	0.6130 (2)	0.0187 (6)
C2	0.4704 (3)	0.2420 (4)	0.5792 (3)	0.0186 (7)
N2	0.5733 (2)	0.1648 (3)	0.6119 (2)	0.0227 (7)
N3	0.3803 (2)	0.1501 (3)	0.5177 (2)	0.0186 (6)
C4	0.2886 (3)	0.2376 (4)	0.4691 (3)	0.0195 (7)
Cl4	0.17783 (7)	0.11931 (10)	0.38568 (7)	0.0246 (3)
C5	0.2745 (3)	0.4087 (4)	0.4785 (3)	0.0182 (7)
C51	0.1943 (3)	0.4955 (4)	0.3876 (3)	0.0214 (7)
O51	0.20011 (19)	0.6406 (3)	0.3598 (2)	0.0245 (6)
C6	0.3614 (3)	0.4822 (4)	0.5689 (3)	0.0189 (7)
N61	0.3501 (2)	0.6334 (3)	0.6160 (2)	0.0188 (6)
C62	0.2380 (3)	0.7273 (4)	0.6073 (3)	0.0225 (8)
C63	0.1350 (3)	0.6336 (4)	0.6493 (3)	0.0281 (8)
C64	0.4488 (3)	0.7008 (4)	0.7017 (3)	0.0211 (7)
C65	0.4339 (3)	0.6638 (4)	0.8289 (3)	0.0267 (8)
H2A	0.6355	0.2226	0.6381	0.027*
H2B	0.5826	0.0744	0.5745	0.027*
H51	0.1306	0.4328	0.3454	0.026*
H62A	0.2134	0.7605	0.5234	0.027*
H62B	0.2530	0.8297	0.6549	0.027*
H63A	0.1105	0.5418	0.5947	0.042*
H63B	0.0674	0.7088	0.6507	0.042*
H63C	0.1610	0.5899	0.7293	0.042*
H64A	0.4528	0.8221	0.6909	0.025*
H64B	0.5251	0.6527	0.6855	0.025*
H65A	0.3589	0.7124	0.8457	0.040*
H65B	0.5009	0.7114	0.8828	0.040*
H65C	0.4321	0.5438	0.8407	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0210 (14)	0.0158 (15)	0.0196 (14)	−0.0007 (11)	0.0045 (11)	−0.0004 (11)
C2	0.0214 (17)	0.0174 (17)	0.0179 (16)	0.0004 (14)	0.0061 (13)	0.0011 (13)
N2	0.0212 (15)	0.0190 (15)	0.0269 (16)	0.0005 (12)	0.0004 (12)	−0.0056 (12)
N3	0.0200 (14)	0.0145 (15)	0.0221 (14)	0.0009 (11)	0.0055 (11)	0.0003 (11)
C4	0.0208 (17)	0.0205 (18)	0.0185 (17)	−0.0015 (14)	0.0075 (13)	−0.0032 (13)
Cl4	0.0231 (4)	0.0193 (4)	0.0307 (5)	−0.0024 (4)	0.0017 (3)	−0.0041 (4)
C5	0.0213 (17)	0.0146 (18)	0.0198 (17)	0.0003 (13)	0.0066 (13)	−0.0009 (13)
C51	0.0210 (18)	0.0218 (19)	0.0217 (17)	0.0011 (14)	0.0043 (14)	−0.0037 (14)
O51	0.0247 (13)	0.0188 (14)	0.0293 (13)	0.0025 (10)	0.0020 (10)	0.0038 (10)
C6	0.0199 (17)	0.0153 (17)	0.0228 (17)	−0.0036 (14)	0.0074 (13)	0.0016 (13)
N61	0.0214 (15)	0.0121 (14)	0.0228 (15)	0.0017 (11)	0.0031 (11)	−0.0018 (11)
C62	0.0237 (18)	0.0141 (17)	0.0298 (19)	0.0060 (13)	0.0042 (15)	−0.0011 (14)
C63	0.029 (2)	0.026 (2)	0.031 (2)	0.0048 (16)	0.0087 (15)	−0.0024 (16)
C64	0.0217 (17)	0.0179 (18)	0.0239 (18)	−0.0044 (14)	0.0043 (14)	−0.0054 (14)
C65	0.0272 (19)	0.024 (2)	0.0285 (19)	−0.0006 (15)	0.0039 (15)	−0.0057 (15)

Geometric parameters (Å, º)

N1—C2	1.326 (4)	N61—C62	1.470 (4)
N1—C6	1.349 (4)	N61—C64	1.472 (4)
C2—N2	1.325 (4)	C62—C63	1.527 (5)
C2—N3	1.367 (4)	C62—H62A	0.99
N2—H2A	0.86	C62—H62B	0.99
N2—H2B	0.86	C63—H63A	0.98
N3—C4	1.308 (4)	C63—H63B	0.98
C4—C5	1.398 (4)	C63—H63C	0.98
C4—Cl4	1.740 (3)	C64—C65	1.513 (5)
C5—C6	1.440 (4)	C64—H64A	0.99
C5—C51	1.450 (4)	C64—H64B	0.99
C51—O51	1.219 (4)	C65—H65A	0.98
C51—H51	0.95	C65—H65B	0.98
C6—N61	1.348 (4)	C65—H65C	0.98
C2—N1—C6	118.1 (3)	N61—C62—H62A	108.6
N2—C2—N1	118.1 (3)	C63—C62—H62A	108.6
N2—C2—N3	116.4 (3)	N61—C62—H62B	108.6
N1—C2—N3	125.3 (3)	C63—C62—H62B	108.6
C2—N2—H2A	118.8	H62A—C62—H62B	107.6
C2—N2—H2B	115.4	C62—C63—H63A	109.5
H2A—N2—H2B	118.6	C62—C63—H63B	109.5
C4—N3—C2	114.0 (3)	H63A—C63—H63B	109.5
N3—C4—C5	126.5 (3)	C62—C63—H63C	109.5
N3—C4—Cl4	113.2 (2)	H63A—C63—H63C	109.5
C5—C4—Cl4	120.2 (2)	H63B—C63—H63C	109.5
C4—C5—C6	112.9 (3)	N61—C64—C65	112.2 (3)
C4—C5—C51	119.4 (3)	N61—C64—H64A	109.2
C6—C5—C51	126.7 (3)	C65—C64—H64A	109.2
O51—C51—C5	126.7 (3)	N61—C64—H64B	109.2
O51—C51—H51	116.7	C65—C64—H64B	109.2
C5—C51—H51	116.7	H64A—C64—H64B	107.9
N61—C6—N1	115.8 (3)	C64—C65—H65A	109.5
N61—C6—C5	124.2 (3)	C64—C65—H65B	109.5
N1—C6—C5	120.1 (3)	H65A—C65—H65B	109.5
C6—N61—C62	125.1 (3)	C64—C65—H65C	109.5
C6—N61—C64	119.4 (3)	H65A—C65—H65C	109.5
C62—N61—C64	114.6 (3)	H65B—C65—H65C	109.5
N61—C62—C63	114.6 (3)
C6—N1—C2—N2	172.7 (3)	C2—N1—C6—C5	−6.2 (4)
C6—N1—C2—N3	−10.7 (5)	C4—C5—C6—N61	−162.6 (3)
N2—C2—N3—C4	−168.3 (3)	C51—C5—C6—N61	29.6 (5)
N1—C2—N3—C4	15.1 (4)	C4—C5—C6—N1	16.4 (4)
C2—N3—C4—C5	−2.4 (5)	C51—C5—C6—N1	−151.4 (3)
C2—N3—C4—Cl4	177.3 (2)	N1—C6—N61—C62	−162.3 (3)
N3—C4—C5—C6	−12.2 (5)	C5—C6—N61—C62	16.7 (5)
Cl4—C4—C5—C6	168.1 (2)	N1—C6—N61—C64	5.4 (4)
N3—C4—C5—C51	156.6 (3)	C5—C6—N61—C64	−175.6 (3)
Cl4—C4—C5—C51	−23.1 (4)	C6—N61—C62—C63	53.7 (4)
C4—C5—C51—O51	−153.8 (3)	C64—N61—C62—C63	−114.5 (3)
C6—C5—C51—O51	13.2 (5)	C6—N61—C64—C65	−93.4 (3)
C2—N1—C6—N61	172.8 (3)	C62—N61—C64—C65	75.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.86	2.16	2.986 (3)	160
N2—H2B···N3^ii	0.86	2.17	3.026 (3)	176

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

(III)

Crystal data

C9H11ClN4O2	F(000) = 504
Mr = 242.67	Dx = 1.545 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2411 reflections
a = 7.3540 (5) Å	θ = 3.4–27.5°
b = 8.2910 (13) Å	µ = 0.36 mm^−1
c = 17.276 (3) Å	T = 120 K
β = 97.962 (9)°	Block, colourless
V = 1043.2 (3) Å^3	0.43 × 0.27 × 0.25 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2411 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1847 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ & ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.862, Tmax = 0.916	k = −10→10
23197 measured reflections	l = −22→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 0.8135P] where P = (Fo^2 + 2Fc^2)/3
2411 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.04078 (6)	0.11154 (6)	0.38668 (3)	0.02457 (14)
O51	0.04412 (17)	0.62528 (15)	0.41908 (8)	0.0199 (3)
O64	0.55062 (17)	0.80546 (16)	0.24959 (8)	0.0220 (3)
N1	0.55786 (19)	0.39370 (17)	0.43026 (8)	0.0141 (3)
N2	0.6843 (2)	0.16390 (19)	0.48805 (9)	0.0178 (3)
N3	0.3866 (2)	0.14625 (18)	0.42907 (9)	0.0168 (3)
N61	0.42737 (19)	0.61957 (18)	0.36997 (9)	0.0154 (3)
C2	0.5403 (2)	0.2400 (2)	0.44905 (10)	0.0153 (4)
C4	0.2386 (2)	0.2298 (2)	0.40523 (10)	0.0164 (4)
C5	0.2268 (2)	0.3973 (2)	0.39611 (10)	0.0150 (4)
C6	0.4057 (2)	0.4716 (2)	0.39821 (10)	0.0148 (4)
C51	0.0596 (2)	0.4806 (2)	0.40591 (10)	0.0174 (4)
C62	0.2953 (2)	0.6987 (2)	0.31075 (11)	0.0184 (4)
C63	0.3810 (2)	0.7207 (2)	0.23665 (11)	0.0203 (4)
C65	0.6784 (2)	0.7207 (2)	0.30431 (11)	0.0204 (4)
C66	0.6050 (2)	0.7030 (2)	0.38147 (11)	0.0171 (4)
H2A	0.7710	0.2258	0.5093	0.021*
H2B	0.6663	0.0700	0.5067	0.021*
H51	−0.0492	0.4176	0.4018	0.021*
H62A	0.2604	0.8050	0.3303	0.022*
H62B	0.1830	0.6320	0.2998	0.022*
H63A	0.4017	0.6134	0.2143	0.024*
H63B	0.2944	0.7805	0.1980	0.024*
H65A	0.7964	0.7801	0.3125	0.024*
H65B	0.7015	0.6126	0.2833	0.024*
H66A	0.6935	0.6410	0.4184	0.021*
H66B	0.5903	0.8109	0.4043	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0143 (2)	0.0211 (2)	0.0371 (3)	−0.00387 (19)	−0.00087 (18)	0.0013 (2)
O51	0.0151 (6)	0.0197 (7)	0.0248 (7)	0.0019 (5)	0.0027 (5)	−0.0005 (6)
O64	0.0183 (7)	0.0262 (7)	0.0212 (7)	−0.0034 (6)	0.0021 (5)	0.0081 (6)
N1	0.0118 (7)	0.0165 (7)	0.0143 (7)	0.0015 (6)	0.0026 (6)	0.0021 (6)
N2	0.0134 (7)	0.0168 (8)	0.0231 (8)	−0.0009 (6)	0.0019 (6)	0.0032 (6)
N3	0.0133 (7)	0.0179 (8)	0.0192 (8)	−0.0002 (6)	0.0014 (6)	0.0009 (6)
N61	0.0102 (7)	0.0190 (8)	0.0169 (7)	−0.0009 (6)	0.0017 (6)	0.0033 (6)
C2	0.0129 (8)	0.0194 (9)	0.0143 (9)	0.0008 (7)	0.0047 (7)	−0.0006 (7)
C4	0.0133 (8)	0.0210 (9)	0.0151 (9)	−0.0026 (7)	0.0024 (7)	−0.0003 (7)
C5	0.0113 (8)	0.0185 (9)	0.0151 (8)	0.0004 (7)	0.0019 (7)	0.0011 (7)
C6	0.0145 (8)	0.0178 (9)	0.0124 (8)	0.0008 (7)	0.0033 (7)	−0.0022 (7)
C51	0.0115 (8)	0.0229 (10)	0.0175 (9)	−0.0003 (7)	0.0009 (7)	0.0010 (7)
C62	0.0140 (8)	0.0201 (9)	0.0209 (10)	0.0023 (7)	0.0014 (7)	0.0057 (7)
C63	0.0177 (9)	0.0235 (10)	0.0189 (9)	−0.0018 (8)	0.0000 (7)	0.0042 (8)
C65	0.0146 (9)	0.0250 (10)	0.0218 (10)	0.0000 (8)	0.0029 (7)	0.0041 (8)
C66	0.0145 (8)	0.0180 (9)	0.0188 (9)	−0.0008 (7)	0.0018 (7)	0.0017 (7)

Geometric parameters (Å, º)

Cl4—C4	1.7466 (18)	C4—C5	1.399 (3)
O51—C51	1.229 (2)	C5—C51	1.441 (2)
O64—C63	1.422 (2)	C5—C6	1.449 (2)
O64—C65	1.423 (2)	C51—H51	0.95
N1—C2	1.326 (2)	C62—C63	1.514 (3)
N1—C6	1.344 (2)	C62—H62A	0.99
N2—C2	1.333 (2)	C62—H62B	0.99
N2—H2A	0.8601	C63—H63A	0.99
N2—H2B	0.86	C63—H63B	0.99
N3—C4	1.308 (2)	C65—C66	1.513 (3)
N3—C2	1.376 (2)	C65—H65A	0.99
N61—C6	1.338 (2)	C65—H65B	0.99
N61—C62	1.464 (2)	C66—H66A	0.99
N61—C66	1.467 (2)	C66—H66B	0.99
C63—O64—C65	110.16 (14)	N61—C62—C63	109.34 (15)
C2—N1—C6	117.34 (15)	N61—C62—H62A	109.8
C2—N2—H2A	115.1	C63—C62—H62A	109.8
C2—N2—H2B	117.7	N61—C62—H62B	109.8
H2A—N2—H2B	121.6	C63—C62—H62B	109.8
C4—N3—C2	113.49 (15)	H62A—C62—H62B	108.3
C6—N61—C62	124.36 (15)	O64—C63—C62	112.66 (15)
C6—N61—C66	122.13 (15)	O64—C63—H63A	109.1
C62—N61—C66	112.04 (14)	C62—C63—H63A	109.1
N1—C2—N2	118.77 (16)	O64—C63—H63B	109.1
N1—C2—N3	125.90 (16)	C62—C63—H63B	109.1
N2—C2—N3	115.27 (16)	H63A—C63—H63B	107.8
N3—C4—C5	126.66 (16)	O64—C65—C66	110.48 (15)
N3—C4—Cl4	113.34 (14)	O64—C65—H65A	109.6
C5—C4—Cl4	119.97 (13)	C66—C65—H65A	109.6
C4—C5—C51	120.22 (16)	O64—C65—H65B	109.6
C4—C5—C6	112.20 (15)	C66—C65—H65B	109.6
C51—C5—C6	125.43 (16)	H65A—C65—H65B	108.1
N61—C6—N1	117.17 (16)	N61—C66—C65	110.25 (15)
N61—C6—C5	122.34 (16)	N61—C66—H66A	109.6
N1—C6—C5	120.48 (16)	C65—C66—H66A	109.6
O51—C51—C5	126.31 (17)	N61—C66—H66B	109.6
O51—C51—H51	116.8	C65—C66—H66B	109.6
C5—C51—H51	116.8	H66A—C66—H66B	108.1
C6—N1—C2—N2	−173.30 (15)	C2—N1—C6—C5	9.5 (2)
C6—N1—C2—N3	9.7 (3)	C4—C5—C6—N61	161.18 (16)
C4—N3—C2—N1	−15.8 (3)	C51—C5—C6—N61	−35.6 (3)
C4—N3—C2—N2	167.08 (15)	C4—C5—C6—N1	−19.8 (2)
C2—N3—C4—C5	2.6 (3)	C51—C5—C6—N1	143.43 (18)
C2—N3—C4—Cl4	−175.63 (12)	C4—C5—C51—O51	160.36 (18)
N3—C4—C5—C51	−150.49 (18)	C6—C5—C51—O51	−1.7 (3)
Cl4—C4—C5—C51	27.6 (2)	C6—N61—C62—C63	−113.98 (18)
N3—C4—C5—C6	13.7 (3)	C66—N61—C62—C63	52.4 (2)
Cl4—C4—C5—C6	−168.16 (13)	C65—O64—C63—C62	59.5 (2)
C62—N61—C6—N1	157.70 (16)	N61—C62—C63—O64	−55.1 (2)
C66—N61—C6—N1	−7.4 (2)	C63—O64—C65—C66	−59.81 (19)
C62—N61—C6—C5	−23.3 (3)	C6—N61—C66—C65	112.30 (18)
C66—N61—C6—C5	171.66 (16)	C62—N61—C66—C65	−54.43 (19)
C2—N1—C6—N61	−171.45 (15)	O64—C65—C66—N61	57.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.86	2.11	2.955 (2)	169
N2—H2B···N3^ii	0.86	2.17	3.023 (2)	171

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

(IV)

Crystal data

C12H17ClN4O	Z = 2
Mr = 268.75	F(000) = 284
Triclinic, P1	Dx = 1.385 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5722 (6) Å	Cell parameters from 2950 reflections
b = 8.7195 (5) Å	θ = 3.1–27.5°
c = 8.7681 (7) Å	µ = 0.29 mm^−1
α = 82.598 (6)°	T = 120 K
β = 82.701 (5)°	Lath, colourless
γ = 88.645 (5)°	0.55 × 0.29 × 0.12 mm
V = 644.63 (8) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2950 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2650 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −11→11
Tmin = 0.856, Tmax = 0.966	k = −11→11
18098 measured reflections	l = −11→11

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.3109P] where P = (Fo^2 + 2Fc^2)/3
2950 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.08515 (3)	0.86418 (3)	0.14913 (4)	0.02344 (10)
O51	0.10958 (10)	0.37823 (10)	0.11711 (10)	0.02188 (19)
N1	0.53482 (11)	0.59963 (11)	0.14624 (11)	0.0155 (2)
N2	0.65263 (12)	0.82596 (11)	0.03284 (12)	0.0191 (2)
N3	0.38672 (12)	0.83698 (11)	0.11058 (12)	0.0171 (2)
N61	0.41428 (11)	0.37877 (11)	0.27134 (11)	0.0160 (2)
C2	0.52251 (14)	0.74955 (13)	0.09633 (13)	0.0158 (2)
C4	0.25849 (14)	0.75455 (13)	0.14349 (13)	0.0165 (2)
C5	0.25019 (13)	0.59279 (13)	0.17197 (13)	0.0159 (2)
C6	0.40092 (13)	0.52129 (13)	0.19577 (13)	0.0147 (2)
C51	0.11337 (14)	0.51353 (14)	0.14201 (14)	0.0196 (2)
C61	0.57301 (13)	0.31075 (13)	0.28449 (13)	0.0159 (2)
C62	0.57286 (15)	0.13447 (13)	0.29619 (15)	0.0205 (2)
C63	0.74075 (16)	0.07226 (15)	0.29846 (15)	0.0253 (3)
C64	0.81615 (16)	0.12409 (16)	0.43179 (16)	0.0261 (3)
C65	0.81133 (15)	0.29982 (15)	0.42411 (15)	0.0229 (3)
C66	0.64347 (14)	0.36293 (14)	0.42108 (14)	0.0187 (2)
C67	0.28209 (15)	0.30183 (14)	0.37147 (15)	0.0214 (3)
H2A	0.7349	0.7723	0.0066	0.023*
H2B	0.6437	0.9209	−0.0062	0.023*
H51	0.0179	0.5710	0.1415	0.024*
H61	0.6426	0.3502	0.1877	0.019*
H62A	0.5282	0.1024	0.2066	0.025*
H62B	0.5065	0.0911	0.3921	0.025*
H63A	0.7394	−0.0421	0.3093	0.030*
H63B	0.8046	0.1096	0.1990	0.030*
H64A	0.7594	0.0774	0.5318	0.031*
H64B	0.9267	0.0876	0.4263	0.031*
H65A	0.8784	0.3458	0.3298	0.027*
H65B	0.8544	0.3303	0.5153	0.027*
H66A	0.6445	0.4773	0.4110	0.022*
H66B	0.5781	0.3247	0.5194	0.022*
H67A	0.2400	0.2225	0.3185	0.032*
H67B	0.1996	0.3781	0.3949	0.032*
H67C	0.3180	0.2532	0.4682	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.02018 (16)	0.02003 (15)	0.02897 (17)	0.00824 (11)	−0.00240 (11)	−0.00103 (12)
O51	0.0208 (4)	0.0190 (4)	0.0262 (5)	−0.0006 (3)	−0.0041 (3)	−0.0032 (3)
N1	0.0168 (5)	0.0128 (4)	0.0165 (5)	0.0012 (4)	−0.0027 (4)	−0.0002 (4)
N2	0.0189 (5)	0.0118 (4)	0.0255 (5)	0.0010 (4)	−0.0017 (4)	0.0006 (4)
N3	0.0195 (5)	0.0131 (4)	0.0184 (5)	0.0031 (4)	−0.0026 (4)	−0.0013 (4)
N61	0.0157 (5)	0.0140 (4)	0.0172 (5)	0.0014 (4)	−0.0022 (4)	0.0019 (4)
C2	0.0188 (6)	0.0145 (5)	0.0148 (5)	0.0020 (4)	−0.0041 (4)	−0.0027 (4)
C4	0.0184 (5)	0.0171 (5)	0.0137 (5)	0.0059 (4)	−0.0032 (4)	−0.0013 (4)
C5	0.0171 (5)	0.0157 (5)	0.0147 (5)	0.0026 (4)	−0.0023 (4)	−0.0007 (4)
C6	0.0180 (5)	0.0134 (5)	0.0129 (5)	0.0023 (4)	−0.0023 (4)	−0.0022 (4)
C51	0.0176 (6)	0.0205 (6)	0.0205 (6)	0.0025 (4)	−0.0036 (4)	−0.0011 (5)
C61	0.0168 (5)	0.0139 (5)	0.0161 (5)	0.0037 (4)	−0.0020 (4)	0.0005 (4)
C62	0.0269 (6)	0.0150 (5)	0.0196 (6)	0.0031 (5)	−0.0063 (5)	0.0003 (4)
C63	0.0319 (7)	0.0200 (6)	0.0240 (6)	0.0116 (5)	−0.0061 (5)	−0.0026 (5)
C64	0.0262 (7)	0.0281 (7)	0.0239 (6)	0.0106 (5)	−0.0071 (5)	−0.0003 (5)
C65	0.0179 (6)	0.0277 (6)	0.0231 (6)	0.0037 (5)	−0.0044 (5)	−0.0019 (5)
C66	0.0185 (6)	0.0191 (5)	0.0187 (6)	0.0032 (4)	−0.0028 (4)	−0.0028 (4)
C67	0.0199 (6)	0.0201 (6)	0.0220 (6)	−0.0010 (5)	−0.0009 (5)	0.0040 (5)

Geometric parameters (Å, º)

Cl4—C4	1.7465 (11)	C61—H61	1.00
O51—C51	1.2290 (15)	C62—C63	1.5275 (17)
N1—C2	1.3301 (15)	C62—H62A	0.99
N1—C6	1.3441 (15)	C62—H62B	0.99
N2—C2	1.3340 (15)	C63—C64	1.5266 (19)
N2—H2A	0.8603	C63—H63A	0.99
N2—H2B	0.86	C63—H63B	0.99
N3—C4	1.3082 (16)	C64—C65	1.5249 (19)
N3—C2	1.3775 (15)	C64—H64A	0.99
N61—C6	1.3405 (15)	C64—H64B	0.99
N61—C67	1.4616 (15)	C65—C66	1.5306 (16)
N61—C61	1.4835 (14)	C65—H65A	0.99
C4—C5	1.4023 (16)	C65—H65B	0.99
C5—C51	1.4441 (17)	C66—H66A	0.99
C5—C6	1.4487 (15)	C66—H66B	0.99
C51—H51	0.95	C67—H67A	0.98
C61—C62	1.5273 (16)	C67—H67B	0.98
C61—C66	1.5308 (16)	C67—H67C	0.98
C2—N1—C6	117.52 (10)	C63—C62—H62B	109.7
C2—N2—H2A	117.7	H62A—C62—H62B	108.2
C2—N2—H2B	118.4	C64—C63—C62	111.39 (10)
H2A—N2—H2B	121.0	C64—C63—H63A	109.4
C4—N3—C2	113.70 (10)	C62—C63—H63A	109.4
C6—N61—C67	121.95 (10)	C64—C63—H63B	109.4
C6—N61—C61	119.35 (10)	C62—C63—H63B	109.4
C67—N61—C61	117.18 (9)	H63A—C63—H63B	108.0
N1—C2—N2	118.40 (10)	C65—C64—C63	110.76 (10)
N1—C2—N3	125.65 (11)	C65—C64—H64A	109.5
N2—C2—N3	115.88 (10)	C63—C64—H64A	109.5
N3—C4—C5	126.41 (11)	C65—C64—H64B	109.5
N3—C4—Cl4	114.03 (9)	C63—C64—H64B	109.5
C5—C4—Cl4	119.56 (9)	H64A—C64—H64B	108.1
C4—C5—C51	120.36 (10)	C64—C65—C66	111.47 (11)
C4—C5—C6	112.53 (10)	C64—C65—H65A	109.3
C51—C5—C6	125.50 (10)	C66—C65—H65A	109.3
N61—C6—N1	117.04 (10)	C64—C65—H65B	109.3
N61—C6—C5	122.60 (10)	C66—C65—H65B	109.3
N1—C6—C5	120.32 (10)	H65A—C65—H65B	108.0
O51—C51—C5	125.76 (11)	C65—C66—C61	109.85 (10)
O51—C51—H51	117.1	C65—C66—H66A	109.7
C5—C51—H51	117.1	C61—C66—H66A	109.7
N61—C61—C62	112.29 (10)	C65—C66—H66B	109.7
N61—C61—C66	111.37 (9)	C61—C66—H66B	109.7
C62—C61—C66	110.60 (9)	H66A—C66—H66B	108.2
N61—C61—H61	107.4	N61—C67—H67A	109.5
C62—C61—H61	107.4	N61—C67—H67B	109.5
C66—C61—H61	107.4	H67A—C67—H67B	109.5
C61—C62—C63	109.77 (10)	N61—C67—H67C	109.5
C61—C62—H62A	109.7	H67A—C67—H67C	109.5
C63—C62—H62A	109.7	H67B—C67—H67C	109.5
C61—C62—H62B	109.7
C6—N1—C2—N2	−173.62 (10)	C51—C5—C6—N61	−36.33 (17)
C6—N1—C2—N3	9.61 (17)	C4—C5—C6—N1	−19.52 (15)
C4—N3—C2—N1	−16.20 (17)	C51—C5—C6—N1	146.00 (12)
C4—N3—C2—N2	166.96 (10)	C4—C5—C51—O51	156.72 (12)
C2—N3—C4—C5	3.51 (17)	C6—C5—C51—O51	−7.8 (2)
C2—N3—C4—Cl4	−175.98 (8)	C6—N61—C61—C62	−151.21 (10)
N3—C4—C5—C51	−153.44 (12)	C67—N61—C61—C62	42.58 (14)
Cl4—C4—C5—C51	26.02 (15)	C6—N61—C61—C66	84.13 (13)
N3—C4—C5—C6	12.91 (17)	C67—N61—C61—C66	−82.08 (12)
Cl4—C4—C5—C6	−167.63 (8)	N61—C61—C62—C63	176.23 (10)
C67—N61—C6—N1	160.41 (11)	C66—C61—C62—C63	−58.69 (13)
C61—N61—C6—N1	−5.12 (15)	C61—C62—C63—C64	57.30 (14)
C67—N61—C6—C5	−17.34 (17)	C62—C63—C64—C65	−55.66 (15)
C61—N61—C6—C5	177.13 (10)	C63—C64—C65—C66	55.32 (14)
C2—N1—C6—N61	−168.26 (10)	C64—C65—C66—C61	−56.62 (14)
C2—N1—C6—C5	9.54 (16)	N61—C61—C66—C65	−176.05 (9)
C4—C5—C6—N61	158.15 (11)	C62—C61—C66—C65	58.35 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.86	2.14	2.9672 (14)	160
N2—H2B···N3^ii	0.86	2.21	3.0727 (14)	178

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

(V)

Crystal data

C14H15ClN4O	Z = 2
Mr = 290.75	F(000) = 304
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9897 (5) Å	Cell parameters from 3191 reflections
b = 8.0922 (4) Å	θ = 3.1–27.5°
c = 11.2786 (7) Å	µ = 0.28 mm^−1
α = 91.602 (4)°	T = 120 K
β = 107.220 (5)°	Block, colourless
γ = 91.776 (5)°	0.29 × 0.28 × 0.21 mm
V = 695.66 (7) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	3191 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2729 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −10→10
Tmin = 0.929, Tmax = 0.944	k = −10→10
19407 measured reflections	l = −14→14

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) = 0.082	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 0.4094P] where P = (Fo^2 + 2Fc^2)/3
3191 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.16086 (5)	0.10251 (4)	0.15234 (4)	0.02196 (10)
O51	0.67154 (13)	0.09713 (12)	0.11486 (9)	0.0192 (2)
N1	0.45541 (15)	0.56822 (14)	0.12673 (10)	0.0140 (2)
N2	0.18588 (15)	0.67590 (14)	0.04287 (11)	0.0172 (2)
N3	0.18943 (15)	0.41157 (14)	0.11221 (11)	0.0152 (2)
N61	0.72480 (15)	0.46270 (14)	0.21076 (10)	0.0139 (2)
C2	0.28169 (17)	0.54892 (17)	0.09391 (12)	0.0139 (3)
C4	0.28395 (18)	0.28129 (17)	0.14313 (12)	0.0150 (3)
C5	0.46476 (17)	0.27389 (17)	0.16236 (12)	0.0141 (3)
C6	0.54986 (17)	0.43489 (17)	0.16665 (12)	0.0132 (3)
C51	0.54016 (18)	0.11612 (17)	0.14745 (13)	0.0174 (3)
C61	0.78125 (18)	0.30538 (17)	0.40537 (13)	0.0164 (3)
C62	0.7823 (2)	0.14111 (19)	0.43793 (14)	0.0230 (3)
C63	0.7301 (2)	0.0948 (2)	0.54002 (16)	0.0300 (4)
C64	0.6779 (2)	0.2127 (2)	0.61128 (15)	0.0292 (4)
C65	0.6772 (2)	0.3769 (2)	0.57982 (14)	0.0263 (3)
C66	0.72774 (19)	0.42296 (19)	0.47748 (14)	0.0211 (3)
C67	0.84363 (17)	0.35478 (17)	0.29666 (13)	0.0162 (3)
C68	0.80377 (18)	0.61997 (17)	0.18582 (13)	0.0168 (3)
C69	0.8290 (2)	0.75189 (18)	0.28807 (14)	0.0218 (3)
H2A	0.2378	0.7508	0.0123	0.021*
H2B	0.0767	0.6537	0.0053	0.021*
H51	0.4823	0.0194	0.1645	0.021*
H62	0.8191	0.0594	0.3900	0.028*
H63	0.7303	−0.0182	0.5607	0.036*
H64	0.6429	0.1813	0.6812	0.035*
H65	0.6419	0.4586	0.6286	0.032*
H66	0.7258	0.5359	0.4564	0.025*
H67A	0.9602	0.4124	0.3289	0.019*
H67B	0.8580	0.2534	0.2501	0.019*
H68A	0.7280	0.6624	0.1074	0.020*
H68B	0.9191	0.5984	0.1738	0.020*
H69A	0.7154	0.7744	0.3006	0.033*
H69B	0.8791	0.8534	0.2646	0.033*
H69C	0.9087	0.7133	0.3653	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.01736 (17)	0.01823 (17)	0.0303 (2)	−0.00224 (12)	0.00687 (14)	0.00692 (14)
O51	0.0185 (5)	0.0184 (5)	0.0211 (5)	0.0030 (4)	0.0061 (4)	0.0008 (4)
N1	0.0141 (5)	0.0149 (5)	0.0127 (5)	0.0009 (4)	0.0033 (4)	0.0001 (4)
N2	0.0133 (6)	0.0170 (6)	0.0209 (6)	0.0008 (4)	0.0039 (5)	0.0039 (5)
N3	0.0137 (5)	0.0177 (6)	0.0143 (5)	0.0006 (4)	0.0039 (4)	0.0021 (4)
N61	0.0127 (5)	0.0151 (6)	0.0130 (5)	0.0003 (4)	0.0025 (4)	0.0003 (4)
C2	0.0154 (6)	0.0158 (6)	0.0104 (6)	0.0009 (5)	0.0038 (5)	−0.0009 (5)
C4	0.0160 (6)	0.0172 (7)	0.0113 (6)	−0.0021 (5)	0.0035 (5)	0.0014 (5)
C5	0.0148 (6)	0.0153 (6)	0.0114 (6)	0.0013 (5)	0.0026 (5)	0.0019 (5)
C6	0.0147 (6)	0.0164 (6)	0.0091 (6)	0.0008 (5)	0.0044 (5)	−0.0013 (5)
C51	0.0175 (7)	0.0146 (7)	0.0189 (7)	0.0003 (5)	0.0035 (5)	0.0026 (5)
C61	0.0123 (6)	0.0193 (7)	0.0140 (6)	0.0013 (5)	−0.0016 (5)	0.0008 (5)
C62	0.0271 (8)	0.0190 (7)	0.0189 (7)	0.0008 (6)	0.0010 (6)	−0.0008 (6)
C63	0.0358 (9)	0.0253 (8)	0.0248 (8)	−0.0044 (7)	0.0026 (7)	0.0069 (6)
C64	0.0265 (8)	0.0407 (10)	0.0202 (8)	−0.0009 (7)	0.0063 (6)	0.0090 (7)
C65	0.0258 (8)	0.0358 (9)	0.0184 (7)	0.0074 (7)	0.0075 (6)	0.0015 (6)
C66	0.0222 (7)	0.0213 (7)	0.0190 (7)	0.0048 (6)	0.0042 (6)	0.0019 (6)
C67	0.0121 (6)	0.0186 (7)	0.0163 (6)	0.0035 (5)	0.0017 (5)	0.0002 (5)
C68	0.0143 (6)	0.0180 (7)	0.0184 (7)	−0.0009 (5)	0.0054 (5)	0.0013 (5)
C69	0.0237 (7)	0.0168 (7)	0.0230 (7)	−0.0028 (6)	0.0047 (6)	−0.0025 (6)

Geometric parameters (Å, º)

Cl4—C4	1.7469 (14)	C61—C67	1.513 (2)
O51—C51	1.2230 (17)	C62—C63	1.393 (2)
N1—C2	1.3292 (17)	C62—H62	0.95
N1—C6	1.3464 (17)	C63—C64	1.382 (3)
N2—C2	1.3394 (18)	C63—H63	0.95
N2—H2A	0.8599	C64—C65	1.385 (2)
N2—H2B	0.8601	C64—H64	0.95
N3—C4	1.3105 (18)	C65—C66	1.387 (2)
N3—C2	1.3687 (17)	C65—H65	0.95
N61—C6	1.3469 (17)	C66—H66	0.95
N61—C67	1.4686 (17)	C67—H67A	0.99
N61—C68	1.4738 (17)	C67—H67B	0.99
C4—C5	1.3994 (19)	C68—C69	1.513 (2)
C5—C6	1.4436 (18)	C68—H68A	0.99
C5—C51	1.4549 (19)	C68—H68B	0.99
C51—H51	0.95	C69—H69A	0.98
C61—C62	1.389 (2)	C69—H69B	0.98
C61—C66	1.392 (2)	C69—H69C	0.98
C2—N1—C6	117.62 (12)	C64—C63—H63	119.9
C2—N2—H2A	116.7	C62—C63—H63	119.9
C2—N2—H2B	116.6	C63—C64—C65	119.41 (15)
H2A—N2—H2B	117.1	C63—C64—H64	120.3
C4—N3—C2	114.22 (12)	C65—C64—H64	120.3
C6—N61—C67	124.10 (11)	C64—C65—C66	120.42 (15)
C6—N61—C68	119.46 (11)	C64—C65—H65	119.8
C67—N61—C68	115.99 (11)	C66—C65—H65	119.8
N1—C2—N2	118.27 (12)	C65—C66—C61	120.66 (14)
N1—C2—N3	125.73 (12)	C65—C66—H66	119.7
N2—C2—N3	115.95 (12)	C61—C66—H66	119.7
N3—C4—C5	126.38 (13)	N61—C67—C61	113.93 (11)
N3—C4—Cl4	113.59 (10)	N61—C67—H67A	108.8
C5—C4—Cl4	119.97 (11)	C61—C67—H67A	108.8
C4—C5—C6	112.88 (12)	N61—C67—H67B	108.8
C4—C5—C51	119.72 (12)	C61—C67—H67B	108.8
C6—C5—C51	125.72 (12)	H67A—C67—H67B	107.7
N1—C6—N61	115.90 (12)	N61—C68—C69	113.83 (12)
N1—C6—C5	120.79 (12)	N61—C68—H68A	108.8
N61—C6—C5	123.30 (12)	C69—C68—H68A	108.8
O51—C51—C5	125.71 (13)	N61—C68—H68B	108.8
O51—C51—H51	117.1	C69—C68—H68B	108.8
C5—C51—H51	117.1	H68A—C68—H68B	107.7
C62—C61—C66	118.52 (14)	C68—C69—H69A	109.5
C62—C61—C67	120.24 (13)	C68—C69—H69B	109.5
C66—C61—C67	121.20 (13)	H69A—C69—H69B	109.5
C61—C62—C63	120.78 (15)	C68—C69—H69C	109.5
C61—C62—H62	119.6	H69A—C69—H69C	109.5
C63—C62—H62	119.6	H69B—C69—H69C	109.5
C64—C63—C62	120.21 (15)
C6—N1—C2—N2	−173.70 (12)	C4—C5—C6—N61	164.82 (12)
C6—N1—C2—N3	9.2 (2)	C51—C5—C6—N61	−30.1 (2)
C4—N3—C2—N1	−13.34 (19)	C4—C5—C51—O51	150.42 (14)
C4—N3—C2—N2	169.51 (12)	C6—C5—C51—O51	−13.7 (2)
C2—N3—C4—C5	2.4 (2)	C66—C61—C62—C63	0.4 (2)
C2—N3—C4—Cl4	−174.52 (9)	C67—C61—C62—C63	178.11 (14)
N3—C4—C5—C6	10.4 (2)	C61—C62—C63—C64	−0.7 (2)
Cl4—C4—C5—C6	−172.83 (9)	C62—C63—C64—C65	0.4 (3)
N3—C4—C5—C51	−155.60 (14)	C63—C64—C65—C66	0.2 (2)
Cl4—C4—C5—C51	21.12 (17)	C64—C65—C66—C61	−0.5 (2)
C2—N1—C6—N61	−173.59 (12)	C62—C61—C66—C65	0.2 (2)
C2—N1—C6—C5	5.82 (18)	C67—C61—C66—C65	−177.50 (13)
C67—N61—C6—N1	157.43 (12)	C6—N61—C67—C61	−46.82 (18)
C68—N61—C6—N1	−14.55 (18)	C68—N61—C67—C61	125.42 (12)
C67—N61—C6—C5	−22.0 (2)	C62—C61—C67—N61	132.45 (14)
C68—N61—C6—C5	166.05 (12)	C66—C61—C67—N61	−49.87 (18)
C4—C5—C6—N1	−14.54 (18)	C6—N61—C68—C69	94.02 (15)
C51—C5—C6—N1	150.51 (13)	C67—N61—C68—C69	−78.60 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.86	2.18	3.0148 (16)	164
N2—H2B···N3^ii	0.86	2.19	3.0407 (17)	172
C65—H65···Cg1^iii	0.95	2.86	3.7061 (17)	149
C68—H68A···Cg1^i	0.99	2.66	3.4643 (15)	138

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

(VI)

Crystal data

C13H13ClN4O	Z = 2
Mr = 276.72	F(000) = 288
Triclinic, P1	Dx = 1.446 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1811 (12) Å	Cell parameters from 2902 reflections
b = 8.8325 (10) Å	θ = 4.0–27.5°
c = 9.3356 (6) Å	µ = 0.30 mm^−1
α = 81.844 (9)°	T = 120 K
β = 82.015 (10)°	Block, colourless
γ = 73.041 (7)°	0.56 × 0.46 × 0.24 mm
V = 635.38 (12) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2902 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ϕ & ω scans	θmax = 27.5°, θmin = 4.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −10→10
Tmin = 0.851, Tmax = 0.932	k = −11→11
15349 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 0.5204P] where P = (Fo^2 + 2Fc^2)/3
2902 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.37106 (18)	0.41564 (17)	0.35666 (16)	0.0167 (3)
C2	0.4146 (2)	0.2600 (2)	0.40258 (19)	0.0162 (3)
N2	0.28800 (19)	0.19310 (17)	0.45152 (17)	0.0200 (3)
N3	0.57793 (18)	0.16112 (16)	0.40022 (16)	0.0168 (3)
C4	0.6990 (2)	0.2342 (2)	0.36126 (19)	0.0159 (3)
Cl4	0.90398 (5)	0.10358 (5)	0.35724 (5)	0.02291 (14)
C5	0.6751 (2)	0.3975 (2)	0.32623 (18)	0.0158 (3)
C51	0.8088 (2)	0.4768 (2)	0.33055 (19)	0.0184 (4)
O51	0.95965 (17)	0.41303 (16)	0.34220 (17)	0.0285 (3)
C6	0.4980 (2)	0.4846 (2)	0.31588 (18)	0.0154 (3)
N61	0.44703 (18)	0.64297 (16)	0.26808 (16)	0.0162 (3)
C61	0.5548 (2)	0.7204 (2)	0.16731 (19)	0.0165 (4)
C62	0.6392 (2)	0.6518 (2)	0.0426 (2)	0.0193 (4)
C63	0.7468 (2)	0.7248 (2)	−0.0521 (2)	0.0226 (4)
C64	0.7673 (2)	0.8674 (2)	−0.0235 (2)	0.0228 (4)
C65	0.6793 (2)	0.9378 (2)	0.0982 (2)	0.0215 (4)
C66	0.5730 (2)	0.8648 (2)	0.1942 (2)	0.0189 (4)
C67	0.2623 (2)	0.7297 (2)	0.2839 (2)	0.0186 (4)
C68	0.1674 (2)	0.7211 (2)	0.1582 (2)	0.0240 (4)
H2A	0.1803	0.2511	0.4528	0.024*
H2B	0.3122	0.0910	0.4825	0.024*
H51	0.7732	0.5898	0.3235	0.022*
H62	0.6231	0.5550	0.0222	0.023*
H63	0.8063	0.6769	−0.1364	0.027*
H64	0.8419	0.9168	−0.0877	0.027*
H65	0.6919	1.0368	0.1163	0.026*
H66	0.5128	0.9135	0.2779	0.023*
H67B	0.2505	0.8428	0.2929	0.022*
H67A	0.2076	0.6853	0.3751	0.022*
H68A	0.2279	0.7540	0.0664	0.036*
H68B	0.0504	0.7920	0.1691	0.036*
H68C	0.1625	0.6116	0.1580	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0148 (7)	0.0142 (7)	0.0199 (8)	−0.0029 (6)	−0.0018 (6)	0.0003 (6)
C2	0.0168 (8)	0.0159 (8)	0.0159 (8)	−0.0039 (7)	−0.0023 (7)	−0.0023 (6)
N2	0.0157 (7)	0.0141 (7)	0.0287 (8)	−0.0038 (6)	−0.0023 (6)	0.0019 (6)
N3	0.0161 (7)	0.0138 (7)	0.0196 (7)	−0.0027 (6)	−0.0023 (6)	−0.0011 (6)
C4	0.0143 (8)	0.0150 (8)	0.0164 (8)	−0.0006 (6)	−0.0022 (6)	−0.0023 (6)
Cl4	0.0161 (2)	0.0168 (2)	0.0316 (3)	0.00076 (16)	−0.00190 (17)	−0.00073 (17)
C5	0.0144 (8)	0.0153 (8)	0.0158 (8)	−0.0024 (6)	−0.0009 (6)	0.0002 (6)
C51	0.0182 (9)	0.0168 (8)	0.0188 (9)	−0.0048 (7)	−0.0006 (7)	0.0009 (7)
O51	0.0150 (6)	0.0253 (7)	0.0440 (9)	−0.0048 (5)	−0.0040 (6)	−0.0006 (6)
C6	0.0160 (8)	0.0142 (8)	0.0150 (8)	−0.0023 (6)	−0.0012 (6)	−0.0029 (6)
N61	0.0135 (7)	0.0131 (7)	0.0202 (8)	−0.0025 (6)	−0.0001 (6)	0.0002 (6)
C61	0.0151 (8)	0.0150 (8)	0.0180 (9)	−0.0029 (6)	−0.0029 (7)	0.0009 (6)
C62	0.0195 (9)	0.0179 (8)	0.0206 (9)	−0.0046 (7)	−0.0031 (7)	−0.0027 (7)
C63	0.0214 (9)	0.0254 (10)	0.0181 (9)	−0.0029 (7)	−0.0009 (7)	−0.0015 (7)
C64	0.0197 (9)	0.0255 (10)	0.0224 (9)	−0.0081 (7)	−0.0032 (7)	0.0049 (7)
C65	0.0236 (9)	0.0160 (8)	0.0255 (10)	−0.0062 (7)	−0.0061 (8)	0.0010 (7)
C66	0.0214 (9)	0.0153 (8)	0.0184 (9)	−0.0022 (7)	−0.0035 (7)	−0.0015 (7)
C67	0.0155 (8)	0.0132 (8)	0.0239 (9)	0.0000 (6)	−0.0007 (7)	−0.0016 (7)
C68	0.0192 (9)	0.0215 (9)	0.0306 (10)	−0.0031 (7)	−0.0061 (8)	−0.0018 (8)

Geometric parameters (Å, º)

N1—C6	1.337 (2)	C61—C62	1.390 (2)
N1—C2	1.338 (2)	C62—C63	1.388 (3)
C2—N2	1.334 (2)	C62—H62	0.95
C2—N3	1.366 (2)	C63—C64	1.385 (3)
N2—H2A	0.88	C63—H63	0.95
N2—H2B	0.88	C64—C65	1.382 (3)
N3—C4	1.318 (2)	C64—H64	0.95
C4—C5	1.395 (2)	C65—C66	1.386 (3)
C4—Cl4	1.7350 (17)	C65—H65	0.95
C5—C6	1.438 (2)	C66—H66	0.95
C5—C51	1.467 (2)	C67—C68	1.517 (3)
C51—O51	1.211 (2)	C67—H67B	0.99
C51—H51	0.95	C67—H67A	0.99
C6—N61	1.365 (2)	C68—H68A	0.98
N61—C61	1.438 (2)	C68—H68B	0.98
N61—C67	1.479 (2)	C68—H68C	0.98
C61—C66	1.387 (2)
C6—N1—C2	117.63 (15)	C63—C62—H62	120.0
N2—C2—N1	117.66 (15)	C61—C62—H62	120.0
N2—C2—N3	116.44 (15)	C64—C63—C62	119.87 (17)
N1—C2—N3	125.86 (16)	C64—C63—H63	120.1
C2—N2—H2A	120.0	C62—C63—H63	120.1
C2—N2—H2B	120.0	C65—C64—C63	120.10 (17)
H2A—N2—H2B	120.0	C65—C64—H64	119.9
C4—N3—C2	114.27 (14)	C63—C64—H64	119.9
N3—C4—C5	126.64 (16)	C64—C65—C66	120.37 (17)
N3—C4—Cl4	112.61 (12)	C64—C65—H65	119.8
C5—C4—Cl4	120.75 (13)	C66—C65—H65	119.8
C4—C5—C6	113.00 (15)	C65—C66—C61	119.64 (17)
C4—C5—C51	123.44 (15)	C65—C66—H66	120.2
C6—C5—C51	122.32 (15)	C61—C66—H66	120.2
O51—C51—C5	126.75 (17)	N61—C67—C68	113.75 (15)
O51—C51—H51	116.6	N61—C67—H67B	108.8
C5—C51—H51	116.6	C68—C67—H67B	108.8
N1—C6—N61	115.38 (15)	N61—C67—H67A	108.8
N1—C6—C5	121.71 (15)	C68—C67—H67A	108.8
N61—C6—C5	122.89 (16)	H67B—C67—H67A	107.7
C6—N61—C61	122.50 (14)	C67—C68—H68A	109.5
C6—N61—C67	119.41 (14)	C67—C68—H68B	109.5
C61—N61—C67	115.77 (13)	H68A—C68—H68B	109.5
C66—C61—C62	120.01 (16)	C67—C68—H68C	109.5
C66—C61—N61	119.76 (15)	H68A—C68—H68C	109.5
C62—C61—N61	120.22 (15)	H68B—C68—H68C	109.5
C63—C62—C61	119.95 (17)
C6—N1—C2—N2	176.06 (16)	N1—C6—N61—C61	−153.43 (16)
C6—N1—C2—N3	−6.0 (3)	C5—C6—N61—C61	28.3 (3)
N2—C2—N3—C4	−175.28 (15)	N1—C6—N61—C67	8.6 (2)
N1—C2—N3—C4	6.7 (3)	C5—C6—N61—C67	−169.72 (15)
C2—N3—C4—C5	1.2 (3)	C6—N61—C61—C66	−133.60 (18)
C2—N3—C4—Cl4	−179.11 (12)	C67—N61—C61—C66	63.8 (2)
N3—C4—C5—C6	−8.4 (3)	C6—N61—C61—C62	47.1 (2)
Cl4—C4—C5—C6	171.95 (12)	C67—N61—C61—C62	−115.51 (18)
N3—C4—C5—C51	159.16 (17)	C66—C61—C62—C63	2.5 (3)
Cl4—C4—C5—C51	−20.5 (2)	N61—C61—C62—C63	−178.18 (16)
C4—C5—C51—O51	12.0 (3)	C61—C62—C63—C64	−1.3 (3)
C6—C5—C51—O51	178.33 (18)	C62—C63—C64—C65	−0.7 (3)
C2—N1—C6—N61	179.15 (15)	C63—C64—C65—C66	1.4 (3)
C2—N1—C6—C5	−2.6 (2)	C64—C65—C66—C61	−0.1 (3)
C4—C5—C6—N1	8.9 (2)	C62—C61—C66—C65	−1.8 (3)
C51—C5—C6—N1	−158.77 (16)	N61—C61—C66—C65	178.86 (16)
C4—C5—C6—N61	−172.94 (16)	C6—N61—C67—C68	−86.95 (19)
C51—C5—C6—N61	19.4 (3)	C61—N61—C67—C68	76.21 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.88	2.23	3.031 (2)	152
N2—H2B···N3^ii	0.88	2.32	3.178 (2)	165

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

(VII)

Crystal data

C12H11ClN4O	Z = 2
Mr = 262.70	F(000) = 272
Triclinic, P1	Dx = 1.470 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0568 (7) Å	Cell parameters from 2729 reflections
b = 8.211 (2) Å	θ = 3.1–27.5°
c = 10.565 (3) Å	µ = 0.32 mm^−1
α = 84.590 (16)°	T = 120 K
β = 82.363 (14)°	Block, colourless
γ = 78.687 (14)°	0.41 × 0.20 × 0.13 mm
V = 593.5 (2) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2729 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.882, Tmax = 0.960	k = −10→10
15054 measured reflections	l = −13→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0602P)^2 + 0.5473P] where P = (Fo^2 + 2Fc^2)/3
2729 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.59 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.63213 (10)	0.04943 (9)	−0.23227 (6)	0.0276 (2)
O51	0.1179 (3)	0.3852 (3)	−0.09322 (19)	0.0328 (5)
N1	0.5938 (3)	0.2896 (3)	0.1345 (2)	0.0214 (5)
N2	0.9020 (3)	0.1404 (3)	0.1475 (2)	0.0281 (6)
N3	0.7625 (3)	0.1070 (3)	−0.0284 (2)	0.0207 (5)
N61	0.2808 (3)	0.4306 (3)	0.1178 (2)	0.0223 (5)
C2	0.7471 (4)	0.1828 (3)	0.0836 (2)	0.0215 (6)
C4	0.6083 (4)	0.1468 (3)	−0.0899 (2)	0.0212 (6)
C5	0.4359 (4)	0.2557 (3)	−0.0510 (2)	0.0211 (6)
C6	0.4376 (4)	0.3261 (3)	0.0686 (2)	0.0201 (6)
C51	0.2720 (4)	0.2909 (4)	−0.1231 (3)	0.0272 (6)
C61	0.1972 (4)	0.3800 (3)	0.3512 (3)	0.0236 (6)
C62	−0.0008 (4)	0.3746 (3)	0.3802 (3)	0.0255 (6)
C63	−0.0638 (4)	0.2696 (4)	0.4798 (3)	0.0296 (7)
C64	0.0675 (5)	0.1682 (4)	0.5527 (3)	0.0317 (7)
C65	0.2640 (5)	0.1714 (4)	0.5244 (3)	0.0328 (7)
C66	0.3288 (4)	0.2768 (4)	0.4246 (3)	0.0288 (7)
C67	0.2650 (4)	0.4976 (3)	0.2433 (2)	0.0230 (6)
H2A	1.0005	0.0661	0.1163	0.034*
H2B	0.9094	0.1923	0.2154	0.034*
H61	0.1563	0.4587	0.0722	0.027*
H51	0.2838	0.2368	−0.2002	0.033*
H62	−0.0926	0.4438	0.3310	0.031*
H63	−0.1987	0.2670	0.4984	0.036*
H64	0.0232	0.0968	0.6216	0.038*
H65	0.3550	0.1011	0.5737	0.039*
H66	0.4639	0.2787	0.4063	0.035*
H67A	0.1722	0.6050	0.2442	0.028*
H67B	0.3935	0.5193	0.2574	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0278 (4)	0.0324 (4)	0.0228 (4)	−0.0022 (3)	−0.0036 (3)	−0.0087 (3)
O51	0.0226 (10)	0.0432 (13)	0.0301 (11)	0.0039 (9)	−0.0054 (9)	−0.0079 (9)
N1	0.0179 (11)	0.0255 (12)	0.0206 (11)	−0.0030 (9)	−0.0016 (9)	−0.0039 (9)
N2	0.0229 (12)	0.0349 (14)	0.0257 (13)	0.0028 (10)	−0.0074 (10)	−0.0095 (11)
N3	0.0188 (11)	0.0233 (12)	0.0198 (12)	−0.0022 (9)	−0.0026 (9)	−0.0031 (9)
N61	0.0205 (11)	0.0255 (12)	0.0190 (11)	0.0002 (9)	−0.0010 (9)	−0.0042 (9)
C2	0.0232 (14)	0.0223 (14)	0.0192 (14)	−0.0055 (11)	−0.0024 (11)	0.0000 (11)
C4	0.0231 (14)	0.0222 (14)	0.0182 (13)	−0.0052 (11)	0.0007 (11)	−0.0027 (11)
C5	0.0223 (13)	0.0237 (14)	0.0176 (13)	−0.0060 (11)	−0.0012 (11)	−0.0005 (11)
C6	0.0204 (13)	0.0201 (14)	0.0195 (13)	−0.0057 (11)	0.0006 (11)	0.0000 (11)
C51	0.0255 (15)	0.0344 (17)	0.0214 (14)	−0.0031 (13)	−0.0022 (12)	−0.0066 (12)
C61	0.0276 (15)	0.0225 (14)	0.0208 (14)	−0.0010 (11)	−0.0033 (11)	−0.0089 (11)
C62	0.0269 (15)	0.0271 (15)	0.0229 (15)	−0.0031 (12)	−0.0050 (12)	−0.0057 (12)
C63	0.0321 (16)	0.0327 (16)	0.0259 (15)	−0.0096 (13)	−0.0011 (13)	−0.0074 (13)
C64	0.0450 (19)	0.0282 (16)	0.0213 (15)	−0.0099 (14)	0.0033 (13)	−0.0020 (12)
C65	0.0422 (18)	0.0324 (17)	0.0216 (15)	0.0006 (14)	−0.0057 (13)	−0.0040 (12)
C66	0.0263 (15)	0.0350 (17)	0.0237 (15)	0.0019 (13)	−0.0050 (12)	−0.0085 (13)
C67	0.0242 (14)	0.0242 (15)	0.0208 (14)	−0.0038 (11)	−0.0011 (11)	−0.0061 (11)

Geometric parameters (Å, º)

Cl4—C4	1.743 (3)	C51—H51	0.95
O51—C51	1.227 (3)	C61—C66	1.394 (4)
N1—C2	1.338 (3)	C61—C62	1.398 (4)
N1—C6	1.351 (3)	C61—C67	1.513 (4)
N2—C2	1.332 (3)	C62—C63	1.380 (4)
N2—H2A	0.88	C62—H62	0.95
N2—H2B	0.88	C63—C64	1.382 (4)
N3—C4	1.312 (3)	C63—H63	0.95
N3—C2	1.370 (3)	C64—C65	1.384 (4)
N61—C6	1.338 (3)	C64—H64	0.95
N61—C67	1.466 (3)	C65—C66	1.388 (4)
N61—H61	1.0337	C65—H65	0.95
C4—C5	1.399 (4)	C66—H66	0.95
C5—C51	1.437 (4)	C67—H67A	0.99
C5—C6	1.440 (4)	C67—H67B	0.99
C2—N1—C6	116.5 (2)	C66—C61—C67	121.1 (3)
C2—N2—H2A	118.4	C62—C61—C67	120.3 (2)
C2—N2—H2B	120.4	C63—C62—C61	120.5 (3)
H2A—N2—H2B	121.0	C63—C62—H62	119.7
C4—N3—C2	114.7 (2)	C61—C62—H62	119.7
C6—N61—C67	123.3 (2)	C62—C63—C64	120.6 (3)
C6—N61—H61	120.7	C62—C63—H63	119.7
C67—N61—H61	115.7	C64—C63—H63	119.7
N2—C2—N1	118.3 (2)	C63—C64—C65	119.5 (3)
N2—C2—N3	114.9 (2)	C63—C64—H64	120.3
N1—C2—N3	126.9 (2)	C65—C64—H64	120.3
N3—C4—C5	126.2 (2)	C64—C65—C66	120.3 (3)
N3—C4—Cl4	113.71 (19)	C64—C65—H65	119.8
C5—C4—Cl4	120.1 (2)	C66—C65—H65	119.8
C4—C5—C51	122.7 (2)	C65—C66—C61	120.5 (3)
C4—C5—C6	113.7 (2)	C65—C66—H66	119.8
C51—C5—C6	123.5 (2)	C61—C66—H66	119.8
N61—C6—N1	118.0 (2)	N61—C67—C61	112.3 (2)
N61—C6—C5	119.9 (2)	N61—C67—H67A	109.2
N1—C6—C5	122.0 (2)	C61—C67—H67A	109.2
O51—C51—C5	125.3 (3)	N61—C67—H67B	109.2
O51—C51—H51	117.4	C61—C67—H67B	109.2
C5—C51—H51	117.4	H67A—C67—H67B	107.9
C66—C61—C62	118.6 (3)
C6—N1—C2—N2	−178.3 (2)	C4—C5—C6—N1	0.6 (4)
C6—N1—C2—N3	0.2 (4)	C51—C5—C6—N1	179.5 (2)
C4—N3—C2—N2	178.8 (2)	C4—C5—C51—O51	180.0 (3)
C4—N3—C2—N1	0.3 (4)	C6—C5—C51—O51	1.2 (5)
C2—N3—C4—C5	−0.3 (4)	C66—C61—C62—C63	0.2 (4)
C2—N3—C4—Cl4	179.74 (18)	C67—C61—C62—C63	−178.9 (2)
N3—C4—C5—C51	−179.0 (3)	C61—C62—C63—C64	0.1 (4)
Cl4—C4—C5—C51	0.9 (4)	C62—C63—C64—C65	−0.6 (4)
N3—C4—C5—C6	−0.1 (4)	C63—C64—C65—C66	0.7 (4)
Cl4—C4—C5—C6	179.83 (19)	C64—C65—C66—C61	−0.4 (4)
C67—N61—C6—N1	−4.5 (4)	C62—C61—C66—C65	0.0 (4)
C67—N61—C6—C5	175.2 (2)	C67—C61—C66—C65	179.1 (2)
C2—N1—C6—N61	179.0 (2)	C6—N61—C67—C61	−84.3 (3)
C2—N1—C6—C5	−0.6 (4)	C66—C61—C67—N61	99.4 (3)
C4—C5—C6—N61	−179.1 (2)	C62—C61—C67—N61	−81.5 (3)
C51—C5—C6—N61	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3^i	0.88	2.14	3.020 (3)	176
N61—H61···O51	1.03	1.97	2.727 (3)	128
N61—H61···O51^ii	1.03	2.10	2.953 (3)	138

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

(VIII)

Crystal data

C12H11ClN4O	Z = 2
Mr = 262.70	F(000) = 272
Triclinic, P1	Dx = 1.490 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9938 (6) Å	Cell parameters from 2681 reflections
b = 7.9544 (10) Å	θ = 3.3–27.5°
c = 10.7507 (14) Å	µ = 0.32 mm^−1
α = 81.191 (11)°	T = 120 K
β = 82.469 (12)°	Block, colourless
γ = 87.333 (10)°	0.37 × 0.27 × 0.18 mm
V = 585.71 (12) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2681 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ & ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.891, Tmax = 0.945	k = −10→10
16227 measured reflections	l = −13→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.2942P] where P = (Fo^2 + 2Fc^2)/3
2681 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.72228 (5)	0.49826 (5)	0.82657 (3)	0.02217 (11)
O51	0.35658 (16)	0.33220 (16)	0.93484 (10)	0.0301 (3)
N1	0.56599 (16)	0.28146 (14)	0.49852 (11)	0.0154 (2)
N3	0.78362 (16)	0.42468 (14)	0.60044 (11)	0.0157 (2)
N2	0.84978 (16)	0.38898 (15)	0.39177 (11)	0.0183 (3)
N61	0.28786 (16)	0.16274 (15)	0.60665 (11)	0.0163 (2)
C2	0.72857 (19)	0.36471 (16)	0.49935 (13)	0.0148 (3)
C4	0.65813 (19)	0.40239 (17)	0.70477 (13)	0.0156 (3)
C5	0.48512 (19)	0.31854 (17)	0.71853 (13)	0.0158 (3)
C6	0.44858 (19)	0.25373 (16)	0.60730 (13)	0.0148 (3)
C51	0.3331 (2)	0.32071 (18)	0.82711 (13)	0.0193 (3)
C61	0.21544 (19)	0.04117 (17)	0.71367 (13)	0.0162 (3)
C62	0.0172 (2)	0.02756 (18)	0.74752 (14)	0.0198 (3)
C63	−0.0540 (2)	−0.09574 (19)	0.84624 (14)	0.0229 (3)
C64	0.0714 (2)	−0.20491 (19)	0.91204 (14)	0.0236 (3)
C65	0.2691 (2)	−0.18997 (19)	0.87914 (14)	0.0224 (3)
C66	0.3410 (2)	−0.06811 (18)	0.77910 (13)	0.0193 (3)
C67	0.2366 (2)	0.13208 (18)	0.48390 (13)	0.0184 (3)
H2A	0.8277	0.3449	0.3270	0.022*
H2B	0.9553	0.4401	0.3924	0.022*
H51	0.2039	0.3122	0.8108	0.023*
H62	−0.0692	0.1025	0.7032	0.024*
H63	−0.1894	−0.1055	0.8689	0.027*
H64	0.0220	−0.2895	0.9793	0.028*
H65	0.3554	−0.2630	0.9250	0.027*
H66	0.4763	−0.0597	0.7555	0.023*
H67A	0.2741	0.2294	0.4190	0.028*
H67B	0.0971	0.1175	0.4907	0.028*
H67C	0.3046	0.0289	0.4602	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.02378 (19)	0.0263 (2)	0.01806 (18)	−0.00996 (14)	−0.00248 (13)	−0.00566 (13)
O51	0.0298 (6)	0.0426 (7)	0.0190 (5)	−0.0145 (5)	0.0028 (4)	−0.0090 (5)
N1	0.0152 (5)	0.0134 (5)	0.0175 (6)	−0.0016 (4)	−0.0020 (4)	−0.0017 (4)
N3	0.0146 (5)	0.0158 (5)	0.0165 (6)	−0.0023 (4)	−0.0019 (4)	−0.0010 (4)
N2	0.0140 (6)	0.0234 (6)	0.0177 (6)	−0.0048 (5)	0.0003 (4)	−0.0042 (5)
N61	0.0154 (6)	0.0168 (6)	0.0170 (6)	−0.0047 (4)	−0.0028 (4)	−0.0016 (4)
C2	0.0139 (6)	0.0121 (6)	0.0178 (6)	0.0012 (5)	−0.0028 (5)	−0.0001 (5)
C4	0.0167 (6)	0.0139 (6)	0.0166 (6)	−0.0008 (5)	−0.0043 (5)	−0.0021 (5)
C5	0.0160 (6)	0.0150 (6)	0.0162 (6)	−0.0017 (5)	−0.0023 (5)	−0.0014 (5)
C6	0.0142 (6)	0.0118 (6)	0.0181 (6)	0.0004 (5)	−0.0034 (5)	−0.0006 (5)
C51	0.0192 (7)	0.0175 (7)	0.0214 (7)	−0.0070 (5)	0.0008 (5)	−0.0040 (5)
C61	0.0175 (7)	0.0151 (6)	0.0163 (6)	−0.0048 (5)	−0.0007 (5)	−0.0030 (5)
C62	0.0169 (7)	0.0205 (7)	0.0220 (7)	−0.0025 (5)	−0.0028 (5)	−0.0021 (6)
C63	0.0174 (7)	0.0258 (8)	0.0253 (7)	−0.0074 (6)	0.0010 (6)	−0.0045 (6)
C64	0.0265 (8)	0.0226 (7)	0.0201 (7)	−0.0089 (6)	0.0012 (6)	0.0005 (6)
C65	0.0239 (7)	0.0220 (7)	0.0206 (7)	−0.0017 (6)	−0.0034 (6)	0.0001 (6)
C66	0.0165 (7)	0.0200 (7)	0.0212 (7)	−0.0031 (5)	−0.0011 (5)	−0.0031 (5)
C67	0.0189 (7)	0.0189 (7)	0.0184 (7)	−0.0034 (5)	−0.0058 (5)	−0.0023 (5)

Geometric parameters (Å, º)

Cl4—C4	1.7289 (14)	C51—H51	0.95
O51—C51	1.2085 (18)	C61—C66	1.387 (2)
N1—C6	1.3330 (18)	C61—C62	1.3916 (19)
N1—C2	1.3439 (17)	C62—C63	1.387 (2)
N3—C4	1.3249 (18)	C62—H62	0.95
N3—C2	1.3574 (17)	C63—C64	1.388 (2)
N2—C2	1.3354 (17)	C63—H63	0.95
N2—H2A	0.8604	C64—C65	1.388 (2)
N2—H2B	0.8602	C64—H64	0.95
N61—C6	1.3663 (17)	C65—C66	1.391 (2)
N61—C61	1.4379 (17)	C65—H65	0.95
N61—C67	1.4697 (17)	C66—H66	0.95
C4—C5	1.3888 (19)	C67—H67A	0.98
C5—C6	1.4290 (19)	C67—H67B	0.98
C5—C51	1.4739 (19)	C67—H67C	0.98
C6—N1—C2	117.05 (12)	C66—C61—N61	120.56 (12)
C4—N3—C2	114.92 (11)	C62—C61—N61	119.47 (12)
C2—N2—H2A	120.3	C63—C62—C61	119.82 (13)
C2—N2—H2B	117.8	C63—C62—H62	120.1
H2A—N2—H2B	121.6	C61—C62—H62	120.1
C6—N61—C61	121.73 (11)	C62—C63—C64	120.38 (13)
C6—N61—C67	118.38 (11)	C62—C63—H63	119.8
C61—N61—C67	115.00 (11)	C64—C63—H63	119.8
N2—C2—N1	117.52 (12)	C65—C64—C63	119.75 (13)
N2—C2—N3	116.41 (12)	C65—C64—H64	120.1
N1—C2—N3	126.06 (12)	C63—C64—H64	120.1
N3—C4—C5	125.55 (12)	C64—C65—C66	120.04 (14)
N3—C4—Cl4	113.56 (10)	C64—C65—H65	120.0
C5—C4—Cl4	120.82 (10)	C66—C65—H65	120.0
C4—C5—C6	114.04 (12)	C61—C66—C65	120.11 (13)
C4—C5—C51	124.35 (12)	C61—C66—H66	119.9
C6—C5—C51	120.70 (12)	C65—C66—H66	119.9
N1—C6—N61	116.50 (12)	N61—C67—H67A	109.5
N1—C6—C5	122.20 (12)	N61—C67—H67B	109.5
N61—C6—C5	121.28 (12)	H67A—C67—H67B	109.5
O51—C51—C5	126.42 (13)	N61—C67—H67C	109.5
O51—C51—H51	116.8	H67A—C67—H67C	109.5
C5—C51—H51	116.8	H67B—C67—H67C	109.5
C66—C61—C62	119.88 (13)
C6—N1—C2—N2	178.18 (12)	C51—C5—C6—N1	165.70 (12)
C6—N1—C2—N3	−0.7 (2)	C4—C5—C6—N61	177.63 (12)
C4—N3—C2—N2	178.39 (11)	C51—C5—C6—N61	−12.8 (2)
C4—N3—C2—N1	−2.75 (19)	C4—C5—C51—O51	−30.8 (2)
C2—N3—C4—C5	2.9 (2)	C6—C5—C51—O51	160.78 (14)
C2—N3—C4—Cl4	−174.10 (9)	C6—N61—C61—C66	−41.77 (19)
N3—C4—C5—C6	0.1 (2)	C67—N61—C61—C66	113.07 (14)
Cl4—C4—C5—C6	176.94 (10)	C6—N61—C61—C62	141.53 (13)
N3—C4—C5—C51	−168.97 (13)	C67—N61—C61—C62	−63.63 (17)
Cl4—C4—C5—C51	7.83 (19)	C66—C61—C62—C63	−0.3 (2)
C2—N1—C6—N61	−177.32 (11)	N61—C61—C62—C63	176.46 (13)
C2—N1—C6—C5	4.10 (19)	C61—C62—C63—C64	0.4 (2)
C61—N61—C6—N1	142.26 (13)	C62—C63—C64—C65	0.3 (2)
C67—N61—C6—N1	−11.77 (18)	C63—C64—C65—C66	−1.2 (2)
C61—N61—C6—C5	−39.15 (19)	C62—C61—C66—C65	−0.6 (2)
C67—N61—C6—C5	166.83 (12)	N61—C61—C66—C65	−177.32 (13)
C4—C5—C6—N1	−3.85 (19)	C64—C65—C66—C61	1.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cg2^i	0.86	2.74	3.5257 (14)	152
N2—H2B···N3^ii	0.86	2.18	3.0374 (17)	178

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

(IX)

Crystal data

C18H15ClN4O	Z = 2
Mr = 338.79	F(000) = 352
Triclinic, P1	Dx = 1.415 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5520 (11) Å	Cell parameters from 3642 reflections
b = 11.1012 (7) Å	θ = 3.2–27.5°
c = 11.4111 (4) Å	µ = 0.25 mm^−1
α = 79.958 (5)°	T = 120 K
β = 84.802 (9)°	Plate, yellow
γ = 77.009 (9)°	0.58 × 0.48 × 0.05 mm
V = 795.21 (15) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	3642 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ϕ & ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −8→8
Tmin = 0.867, Tmax = 0.988	k = −14→14
19326 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0241P)^2 + 0.4915P] where P = (Fo^2 + 2Fc^2)/3
3642 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.58889 (7)	0.71360 (4)	0.30061 (4)	0.02553 (12)
O51	0.2480 (2)	0.64590 (13)	0.18932 (14)	0.0371 (4)
N1	0.6929 (2)	0.30293 (13)	0.42419 (12)	0.0203 (3)
N2	0.9672 (3)	0.32794 (14)	0.52188 (14)	0.0278 (4)
N3	0.7843 (2)	0.50333 (13)	0.40947 (12)	0.0200 (3)
N61	0.4245 (2)	0.27529 (13)	0.32288 (13)	0.0208 (3)
C2	0.8083 (3)	0.37920 (16)	0.45084 (15)	0.0198 (4)
C4	0.6211 (3)	0.55272 (16)	0.34335 (15)	0.0190 (4)
C5	0.4809 (3)	0.48764 (16)	0.31274 (15)	0.0187 (4)
C6	0.5339 (3)	0.35550 (16)	0.35337 (15)	0.0186 (4)
C51	0.2800 (3)	0.54878 (18)	0.25838 (17)	0.0259 (4)
C61	0.6504 (3)	0.06368 (16)	0.31124 (17)	0.0263 (4)
C62	0.6169 (4)	0.02933 (18)	0.20385 (18)	0.0356 (5)
C63	0.7806 (4)	−0.03815 (19)	0.1407 (2)	0.0470 (6)
C64	0.9789 (4)	−0.0739 (2)	0.1842 (2)	0.0508 (7)
C65	1.0133 (4)	−0.04222 (19)	0.2918 (2)	0.0446 (6)
C66	0.8506 (3)	0.02662 (18)	0.3544 (2)	0.0333 (5)
C67	0.4741 (3)	0.14145 (17)	0.37834 (17)	0.0257 (4)
C611	0.3194 (3)	0.30034 (16)	0.21304 (16)	0.0207 (4)
C612	0.4158 (3)	0.34625 (16)	0.10680 (16)	0.0228 (4)
C613	0.3178 (3)	0.36222 (18)	0.00097 (18)	0.0319 (5)
C614	0.1264 (3)	0.3295 (2)	0.0004 (2)	0.0383 (5)
C615	0.0322 (3)	0.2819 (2)	0.1062 (2)	0.0367 (5)
C616	0.1255 (3)	0.26871 (18)	0.21285 (19)	0.0285 (4)
H2B	1.0390	0.3778	0.5436	0.033*
H2A	0.9802	0.2494	0.5563	0.033*
H51	0.1657	0.5082	0.2796	0.031*
H62	0.4806	0.0524	0.1738	0.043*
H63	0.7564	−0.0600	0.0671	0.056*
H64	1.0910	−0.1199	0.1406	0.061*
H65	1.1488	−0.0678	0.3227	0.053*
H66	0.8759	0.0488	0.4276	0.040*
H67A	0.3469	0.1066	0.3816	0.031*
H67B	0.5136	0.1355	0.4612	0.031*
H612	0.5491	0.3668	0.1066	0.027*
H613	0.3823	0.3958	−0.0716	0.038*
H614	0.0601	0.3397	−0.0724	0.046*
H615	−0.0981	0.2580	0.1056	0.044*
H616	0.0578	0.2382	0.2856	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0330 (3)	0.0174 (2)	0.0280 (2)	−0.00704 (18)	−0.00748 (19)	−0.00352 (18)
O51	0.0343 (8)	0.0247 (8)	0.0529 (10)	0.0012 (6)	−0.0203 (7)	−0.0078 (7)
N1	0.0249 (8)	0.0203 (8)	0.0180 (7)	−0.0087 (6)	−0.0023 (6)	−0.0030 (6)
N2	0.0389 (10)	0.0196 (8)	0.0282 (9)	−0.0108 (7)	−0.0156 (7)	−0.0001 (7)
N3	0.0253 (8)	0.0201 (8)	0.0162 (7)	−0.0079 (6)	−0.0031 (6)	−0.0028 (6)
N61	0.0233 (8)	0.0199 (8)	0.0223 (8)	−0.0104 (6)	−0.0011 (6)	−0.0043 (6)
C2	0.0250 (9)	0.0205 (9)	0.0160 (9)	−0.0078 (7)	−0.0014 (7)	−0.0046 (7)
C4	0.0226 (9)	0.0184 (9)	0.0164 (9)	−0.0048 (7)	0.0019 (7)	−0.0049 (7)
C5	0.0198 (9)	0.0182 (9)	0.0190 (9)	−0.0037 (7)	−0.0001 (7)	−0.0067 (7)
C6	0.0202 (9)	0.0224 (9)	0.0154 (9)	−0.0081 (7)	0.0031 (7)	−0.0068 (7)
C51	0.0219 (10)	0.0241 (10)	0.0353 (11)	−0.0036 (8)	−0.0032 (8)	−0.0149 (9)
C61	0.0360 (11)	0.0150 (9)	0.0289 (10)	−0.0107 (8)	−0.0008 (8)	0.0008 (7)
C62	0.0540 (14)	0.0180 (10)	0.0347 (12)	−0.0063 (9)	−0.0060 (10)	−0.0042 (9)
C63	0.0762 (19)	0.0210 (11)	0.0394 (13)	−0.0018 (11)	0.0030 (12)	−0.0073 (10)
C64	0.0615 (17)	0.0175 (10)	0.0638 (17)	−0.0008 (11)	0.0233 (14)	−0.0039 (11)
C65	0.0407 (13)	0.0191 (10)	0.0692 (17)	−0.0063 (9)	0.0013 (12)	0.0034 (11)
C66	0.0377 (12)	0.0190 (9)	0.0431 (12)	−0.0097 (9)	−0.0044 (10)	0.0014 (9)
C67	0.0324 (11)	0.0237 (10)	0.0252 (10)	−0.0163 (8)	0.0004 (8)	−0.0026 (8)
C611	0.0197 (9)	0.0173 (9)	0.0268 (10)	−0.0030 (7)	−0.0039 (7)	−0.0078 (7)
C612	0.0211 (9)	0.0212 (9)	0.0278 (10)	−0.0034 (7)	−0.0044 (8)	−0.0084 (8)
C613	0.0423 (12)	0.0272 (11)	0.0278 (11)	−0.0047 (9)	−0.0093 (9)	−0.0084 (8)
C614	0.0408 (13)	0.0323 (12)	0.0450 (13)	0.0024 (10)	−0.0257 (11)	−0.0160 (10)
C615	0.0202 (10)	0.0340 (11)	0.0613 (15)	−0.0008 (9)	−0.0138 (10)	−0.0227 (11)
C616	0.0215 (9)	0.0266 (10)	0.0417 (12)	−0.0075 (8)	0.0016 (8)	−0.0155 (9)

Geometric parameters (Å, º)

Cl4—C4	1.7370 (18)	C63—C64	1.381 (4)
O51—C51	1.208 (2)	C63—H63	0.95
N1—C6	1.339 (2)	C64—C65	1.385 (3)
N1—C2	1.342 (2)	C64—H64	0.95
N2—C2	1.338 (2)	C65—C66	1.384 (3)
N2—H2B	0.88	C65—H65	0.95
N2—H2A	0.88	C66—H66	0.95
N3—C4	1.323 (2)	C67—H67A	0.99
N3—C2	1.355 (2)	C67—H67B	0.99
N61—C6	1.367 (2)	C611—C612	1.385 (3)
N61—C611	1.439 (2)	C611—C616	1.392 (2)
N61—C67	1.485 (2)	C612—C613	1.385 (3)
C4—C5	1.390 (2)	C612—H612	0.95
C5—C6	1.432 (2)	C613—C614	1.382 (3)
C5—C51	1.476 (2)	C613—H613	0.95
C51—H51	0.95	C614—C615	1.381 (3)
C61—C66	1.391 (3)	C614—H614	0.95
C61—C62	1.395 (3)	C615—C616	1.382 (3)
C61—C67	1.513 (3)	C615—H615	0.95
C62—C63	1.385 (3)	C616—H616	0.95
C62—H62	0.95
C6—N1—C2	116.83 (15)	C63—C64—H64	120.2
C2—N2—H2B	118.2	C65—C64—H64	120.2
C2—N2—H2A	118.9	C66—C65—C64	120.2 (2)
H2B—N2—H2A	121.8	C66—C65—H65	119.9
C4—N3—C2	115.06 (14)	C64—C65—H65	119.9
C6—N61—C611	122.46 (15)	C65—C66—C61	120.8 (2)
C6—N61—C67	119.02 (15)	C65—C66—H66	119.6
C611—N61—C67	114.93 (13)	C61—C66—H66	119.6
N2—C2—N1	117.43 (16)	N61—C67—C61	112.83 (14)
N2—C2—N3	116.26 (15)	N61—C67—H67A	109.0
N1—C2—N3	126.26 (16)	C61—C67—H67A	109.0
N3—C4—C5	125.49 (16)	N61—C67—H67B	109.0
N3—C4—Cl4	113.00 (13)	C61—C67—H67B	109.0
C5—C4—Cl4	121.46 (13)	H67A—C67—H67B	107.8
C4—C5—C6	113.92 (15)	C612—C611—C616	119.88 (17)
C4—C5—C51	123.74 (16)	C612—C611—N61	120.80 (15)
C6—C5—C51	121.82 (15)	C616—C611—N61	119.13 (17)
N1—C6—N61	115.85 (15)	C613—C612—C611	119.92 (17)
N1—C6—C5	122.07 (15)	C613—C612—H612	120.0
N61—C6—C5	122.07 (16)	C611—C612—H612	120.0
O51—C51—C5	125.74 (18)	C614—C613—C612	120.3 (2)
O51—C51—H51	117.1	C614—C613—H613	119.9
C5—C51—H51	117.1	C612—C613—H613	119.9
C66—C61—C62	118.55 (19)	C615—C614—C613	119.67 (19)
C66—C61—C67	120.67 (18)	C615—C614—H614	120.2
C62—C61—C67	120.77 (18)	C613—C614—H614	120.2
C63—C62—C61	120.5 (2)	C614—C615—C616	120.66 (19)
C63—C62—H62	119.7	C614—C615—H615	119.7
C61—C62—H62	119.7	C616—C615—H615	119.7
C64—C63—C62	120.4 (2)	C615—C616—C611	119.56 (19)
C64—C63—H63	119.8	C615—C616—H616	120.2
C62—C63—H63	119.8	C611—C616—H616	120.2
C63—C64—C65	119.6 (2)
C6—N1—C2—N2	179.77 (16)	C67—C61—C62—C63	177.74 (18)
C6—N1—C2—N3	−2.6 (3)	C61—C62—C63—C64	0.9 (3)
C4—N3—C2—N2	−177.43 (16)	C62—C63—C64—C65	0.2 (3)
C4—N3—C2—N1	4.9 (3)	C63—C64—C65—C66	−1.1 (3)
C2—N3—C4—C5	−1.4 (2)	C64—C65—C66—C61	0.8 (3)
C2—N3—C4—Cl4	176.24 (12)	C62—C61—C66—C65	0.4 (3)
N3—C4—C5—C6	−3.7 (3)	C67—C61—C66—C65	−178.58 (17)
Cl4—C4—C5—C6	178.86 (12)	C6—N61—C67—C61	−86.92 (19)
N3—C4—C5—C51	168.10 (17)	C611—N61—C67—C61	72.27 (19)
Cl4—C4—C5—C51	−9.3 (2)	C66—C61—C67—N61	103.74 (19)
C2—N1—C6—N61	177.08 (15)	C62—C61—C67—N61	−75.2 (2)
C2—N1—C6—C5	−3.3 (2)	C6—N61—C611—C612	43.4 (2)
C611—N61—C6—N1	−151.63 (15)	C67—N61—C611—C612	−115.03 (18)
C67—N61—C6—N1	5.9 (2)	C6—N61—C611—C616	−141.62 (17)
C611—N61—C6—C5	28.7 (2)	C67—N61—C611—C616	60.0 (2)
C67—N61—C6—C5	−173.71 (15)	C616—C611—C612—C613	0.9 (3)
C4—C5—C6—N1	6.2 (2)	N61—C611—C612—C613	175.89 (16)
C51—C5—C6—N1	−165.86 (16)	C611—C612—C613—C614	−1.7 (3)
C4—C5—C6—N61	−174.25 (15)	C612—C613—C614—C615	0.6 (3)
C51—C5—C6—N61	13.7 (3)	C613—C614—C615—C616	1.1 (3)
C4—C5—C51—O51	34.1 (3)	C614—C615—C616—C611	−1.9 (3)
C6—C5—C51—O51	−154.70 (18)	C612—C611—C616—C615	0.8 (3)
C66—C61—C62—C63	−1.2 (3)	N61—C611—C616—C615	−174.22 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3^i	0.88	2.10	2.981 (2)	178
C614—H614···O51^ii	0.95	2.48	3.352 (3)	153

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

(X)

Crystal data

C15H12ClN5O	F(000) = 648
Mr = 313.75	Dx = 1.514 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3149 reflections
a = 7.5716 (7) Å	θ = 3.1–27.5°
b = 16.6432 (18) Å	µ = 0.29 mm^−1
c = 10.9450 (7) Å	T = 120 K
β = 93.549 (6)°	Lath, colourless
V = 1376.6 (2) Å^3	0.51 × 0.25 × 0.10 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	3149 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.867, Tmax = 0.972	k = −21→21
32885 measured reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 1.2389P] where P = (Fo^2 + 2Fc^2)/3
3149 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl4	0.28800 (8)	0.36592 (3)	0.23753 (5)	0.02223 (16)
O51	0.1645 (2)	0.13615 (9)	0.38717 (14)	0.0212 (4)
N1	0.3950 (2)	0.31159 (10)	0.63242 (16)	0.0174 (4)
N2	0.5171 (3)	0.43677 (11)	0.64767 (16)	0.0210 (4)
N3	0.3967 (2)	0.40048 (10)	0.45792 (16)	0.0171 (4)
N61	0.2690 (2)	0.18541 (10)	0.61607 (16)	0.0182 (4)
N62	0.3305 (2)	0.02393 (11)	0.68429 (16)	0.0186 (4)
C2	0.4343 (3)	0.38122 (13)	0.57843 (19)	0.0170 (4)
C4	0.3260 (3)	0.34162 (13)	0.39188 (19)	0.0170 (4)
C5	0.2806 (3)	0.26535 (13)	0.43352 (19)	0.0166 (4)
C6	0.3158 (3)	0.25521 (12)	0.56319 (19)	0.0162 (4)
C51	0.2037 (3)	0.20430 (13)	0.3539 (2)	0.0195 (5)
C61	0.2949 (3)	0.16556 (13)	0.74230 (19)	0.0166 (4)
C62	0.3306 (3)	0.08584 (13)	0.7749 (2)	0.0175 (4)
C63	0.3638 (3)	0.06497 (14)	0.8970 (2)	0.0211 (5)
C64	0.3618 (3)	0.12309 (14)	0.9881 (2)	0.0230 (5)
C65	0.3172 (3)	0.20096 (14)	0.9559 (2)	0.0227 (5)
C66	0.2827 (3)	0.22276 (13)	0.8345 (2)	0.0210 (5)
C622	0.1825 (3)	−0.00186 (13)	0.6163 (2)	0.0196 (5)
C623	0.2245 (3)	−0.07029 (13)	0.5560 (2)	0.0211 (5)
C624	0.4045 (3)	−0.08700 (13)	0.5875 (2)	0.0228 (5)
C625	0.4664 (3)	−0.02910 (13)	0.6674 (2)	0.0222 (5)
H2A	0.5392	0.4259	0.7239	0.025*
H2B	0.5399	0.4828	0.6166	0.025*
H61	0.2321	0.1495	0.5641	0.022*
H51	0.1817	0.2174	0.2699	0.023*
H63	0.3881	0.0106	0.9184	0.025*
H64	0.3907	0.1094	1.0712	0.028*
H65	0.3101	0.2404	1.0181	0.027*
H66	0.2507	0.2765	0.8142	0.025*
H622	0.0700	0.0237	0.6120	0.024*
H623	0.1472	−0.1010	0.5027	0.025*
H624	0.4706	−0.1307	0.5584	0.027*
H625	0.5828	−0.0259	0.7049	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0292 (3)	0.0221 (3)	0.0151 (3)	−0.0020 (2)	−0.0017 (2)	0.0040 (2)
O51	0.0244 (9)	0.0175 (8)	0.0210 (8)	−0.0033 (6)	−0.0031 (6)	−0.0002 (6)
N1	0.0217 (10)	0.0137 (9)	0.0168 (9)	−0.0006 (7)	0.0003 (7)	−0.0001 (7)
N2	0.0321 (11)	0.0165 (9)	0.0143 (9)	−0.0030 (8)	−0.0006 (8)	0.0016 (7)
N3	0.0215 (10)	0.0150 (9)	0.0147 (9)	−0.0006 (7)	0.0003 (7)	0.0017 (7)
N61	0.0259 (11)	0.0130 (9)	0.0155 (9)	−0.0008 (7)	−0.0001 (7)	0.0010 (7)
N62	0.0201 (10)	0.0159 (9)	0.0196 (9)	0.0006 (7)	0.0011 (7)	0.0020 (7)
C2	0.0181 (11)	0.0164 (10)	0.0166 (10)	0.0029 (8)	0.0023 (8)	−0.0004 (8)
C4	0.0164 (11)	0.0192 (11)	0.0154 (10)	0.0020 (8)	−0.0005 (8)	0.0016 (8)
C5	0.0176 (11)	0.0175 (11)	0.0147 (10)	0.0001 (8)	−0.0001 (8)	0.0004 (8)
C6	0.0161 (11)	0.0159 (10)	0.0165 (11)	0.0019 (8)	0.0011 (8)	0.0011 (8)
C51	0.0195 (12)	0.0211 (12)	0.0175 (11)	−0.0001 (9)	−0.0010 (9)	0.0019 (9)
C61	0.0162 (11)	0.0169 (10)	0.0167 (10)	−0.0015 (8)	0.0015 (8)	0.0029 (8)
C62	0.0175 (11)	0.0165 (10)	0.0184 (10)	−0.0020 (9)	0.0008 (8)	−0.0023 (8)
C63	0.0212 (12)	0.0176 (11)	0.0243 (12)	0.0022 (9)	−0.0010 (9)	0.0054 (9)
C64	0.0254 (13)	0.0288 (12)	0.0145 (10)	−0.0031 (10)	−0.0008 (9)	0.0022 (9)
C65	0.0275 (13)	0.0229 (12)	0.0180 (11)	−0.0052 (10)	0.0041 (9)	−0.0026 (9)
C66	0.0272 (13)	0.0153 (11)	0.0211 (11)	−0.0002 (9)	0.0056 (9)	0.0014 (9)
C622	0.0201 (11)	0.0190 (11)	0.0194 (11)	−0.0010 (9)	−0.0007 (9)	0.0017 (9)
C623	0.0278 (13)	0.0185 (11)	0.0170 (11)	−0.0020 (9)	0.0009 (9)	0.0001 (9)
C624	0.0249 (13)	0.0175 (11)	0.0269 (12)	0.0018 (9)	0.0081 (10)	−0.0012 (9)
C625	0.0209 (12)	0.0199 (11)	0.0256 (12)	0.0037 (9)	0.0010 (9)	0.0016 (9)

Geometric parameters (Å, º)

Cl4—C4	1.744 (2)	C51—H51	0.95
O51—C51	1.233 (3)	C61—C66	1.395 (3)
N1—C6	1.326 (3)	C61—C62	1.396 (3)
N1—C2	1.343 (3)	C62—C63	1.389 (3)
N2—C2	1.328 (3)	C63—C64	1.390 (3)
N2—H2A	0.8599	C63—H63	0.95
N2—H2B	0.8599	C64—C65	1.379 (3)
N3—C4	1.312 (3)	C64—H64	0.95
N3—C2	1.370 (3)	C65—C66	1.386 (3)
N61—C6	1.355 (3)	C65—H65	0.95
N61—C61	1.422 (3)	C66—H66	0.95
N61—H61	0.86	C622—C623	1.364 (3)
N62—C622	1.375 (3)	C622—H622	0.95
N62—C625	1.377 (3)	C623—C624	1.413 (3)
N62—C62	1.430 (3)	C623—H623	0.95
C4—C5	1.399 (3)	C624—C625	1.365 (3)
C5—C6	1.438 (3)	C624—H624	0.95
C5—C51	1.438 (3)	C625—H625	0.95
C6—N1—C2	117.65 (18)	C62—C61—N61	118.80 (19)
C2—N2—H2A	117.7	C63—C62—C61	120.3 (2)
C2—N2—H2B	119.6	C63—C62—N62	118.65 (19)
H2A—N2—H2B	122.6	C61—C62—N62	121.07 (19)
C4—N3—C2	114.16 (18)	C62—C63—C64	120.5 (2)
C6—N61—C61	126.15 (18)	C62—C63—H63	119.8
C6—N61—H61	113.4	C64—C63—H63	119.8
C61—N61—H61	120.1	C65—C64—C63	118.9 (2)
C622—N62—C625	108.57 (18)	C65—C64—H64	120.5
C622—N62—C62	124.45 (18)	C63—C64—H64	120.5
C625—N62—C62	125.90 (19)	C64—C65—C66	121.3 (2)
N2—C2—N1	117.34 (19)	C64—C65—H65	119.4
N2—C2—N3	116.70 (19)	C66—C65—H65	119.4
N1—C2—N3	125.96 (19)	C65—C66—C61	119.9 (2)
N3—C4—C5	126.74 (19)	C65—C66—H66	120.1
N3—C4—Cl4	113.45 (16)	C61—C66—H66	120.1
C5—C4—Cl4	119.81 (16)	C623—C622—N62	108.4 (2)
C4—C5—C6	113.21 (18)	C623—C622—H622	125.8
C4—C5—C51	122.83 (19)	N62—C622—H622	125.8
C6—C5—C51	123.96 (19)	C622—C623—C624	107.3 (2)
N1—C6—N61	118.93 (18)	C622—C623—H623	126.4
N1—C6—C5	122.05 (19)	C624—C623—H623	126.4
N61—C6—C5	119.01 (19)	C625—C624—C623	107.8 (2)
O51—C51—C5	124.5 (2)	C625—C624—H624	126.1
O51—C51—H51	117.7	C623—C624—H624	126.1
C5—C51—H51	117.7	C624—C625—N62	108.0 (2)
C66—C61—C62	118.97 (19)	C624—C625—H625	126.0
C66—C61—N61	122.21 (19)	N62—C625—H625	126.0
C6—N1—C2—N2	−178.58 (19)	C66—C61—C62—C63	−3.9 (3)
C6—N1—C2—N3	1.5 (3)	N61—C61—C62—C63	177.3 (2)
C4—N3—C2—N2	175.57 (19)	C66—C61—C62—N62	175.0 (2)
C4—N3—C2—N1	−4.5 (3)	N61—C61—C62—N62	−3.8 (3)
C2—N3—C4—C5	2.9 (3)	C622—N62—C62—C63	111.5 (2)
C2—N3—C4—Cl4	−177.37 (15)	C625—N62—C62—C63	−55.3 (3)
N3—C4—C5—C6	1.2 (3)	C622—N62—C62—C61	−67.4 (3)
Cl4—C4—C5—C6	−178.50 (16)	C625—N62—C62—C61	125.9 (2)
N3—C4—C5—C51	−179.8 (2)	C61—C62—C63—C64	0.1 (3)
Cl4—C4—C5—C51	0.5 (3)	N62—C62—C63—C64	−178.8 (2)
C2—N1—C6—N61	−177.72 (19)	C62—C63—C64—C65	3.3 (3)
C2—N1—C6—C5	3.3 (3)	C63—C64—C65—C66	−3.0 (4)
C61—N61—C6—N1	0.6 (3)	C64—C65—C66—C61	−0.8 (4)
C61—N61—C6—C5	179.6 (2)	C62—C61—C66—C65	4.2 (3)
C4—C5—C6—N1	−4.5 (3)	N61—C61—C66—C65	−177.0 (2)
C51—C5—C6—N1	176.5 (2)	C625—N62—C622—C623	−0.5 (2)
C4—C5—C6—N61	176.52 (19)	C62—N62—C622—C623	−169.19 (19)
C51—C5—C6—N61	−2.4 (3)	N62—C622—C623—C624	−0.2 (2)
C4—C5—C51—O51	178.9 (2)	C622—C623—C624—C625	0.9 (3)
C6—C5—C51—O51	−2.2 (4)	C623—C624—C625—N62	−1.2 (3)
C6—N61—C61—C66	35.0 (3)	C622—N62—C625—C624	1.1 (2)
C6—N61—C61—C62	−146.3 (2)	C62—N62—C625—C624	169.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.86	2.22	3.038 (2)	158
N2—H2B···N3^ii	0.86	2.17	3.032 (3)	178
N61—H61···O51	0.86	1.98	2.707 (2)	141

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

(XI)

Crystal data

C11H16ClN5O2	Z = 2
Mr = 285.74	F(000) = 300
Triclinic, P1	Dx = 1.480 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2147 (6) Å	Cell parameters from 2936 reflections
b = 8.8563 (10) Å	θ = 4.0–27.5°
c = 10.2855 (12) Å	µ = 0.31 mm^−1
α = 84.856 (10)°	T = 120 K
β = 85.296 (10)°	Block, colourless
γ = 79.092 (7)°	0.58 × 0.29 × 0.22 mm
V = 641.28 (12) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2936 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ & ω scans	θmax = 27.5°, θmin = 4.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.843, Tmax = 0.936	k = −11→11
15336 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0442P)^2 + 0.4199P] where P = (Fo^2 + 2Fc^2)/3
2936 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	1.03833 (19)	0.19931 (16)	0.42088 (13)	0.0173 (3)
C2	1.2103 (2)	0.12399 (18)	0.45074 (15)	0.0171 (3)
N2	1.27779 (19)	0.14946 (17)	0.56113 (13)	0.0209 (3)
N3	1.32379 (18)	0.01454 (15)	0.37787 (13)	0.0161 (3)
C4	1.2683 (2)	0.00979 (18)	0.26145 (16)	0.0161 (3)
Cl4	1.42263 (5)	−0.12121 (5)	0.16646 (4)	0.02160 (13)
C5	1.1057 (2)	0.09739 (18)	0.20756 (15)	0.0152 (3)
C51	1.1005 (2)	0.12611 (19)	0.06761 (16)	0.0186 (3)
O51	0.98395 (17)	0.21939 (15)	0.00677 (12)	0.0249 (3)
C6	0.9799 (2)	0.18337 (18)	0.30393 (15)	0.0151 (3)
N61	0.80235 (18)	0.25359 (15)	0.27918 (13)	0.0156 (3)
C62	0.6818 (2)	0.18210 (19)	0.20446 (16)	0.0181 (3)
C65	0.5348 (2)	0.46549 (19)	0.31328 (16)	0.0191 (3)
C63	0.5254 (2)	0.30174 (19)	0.14700 (16)	0.0174 (3)
N64	0.41036 (18)	0.38617 (15)	0.25008 (13)	0.0158 (3)
C641	0.2497 (2)	0.49297 (19)	0.19543 (15)	0.0174 (3)
C642	0.1194 (2)	0.57779 (19)	0.29963 (16)	0.0182 (3)
O64	−0.05701 (16)	0.65227 (15)	0.24939 (12)	0.0221 (3)
C66	0.6914 (2)	0.3512 (2)	0.37695 (16)	0.0193 (3)
H2A	1.2098	0.2151	0.6136	0.025*
H2B	1.3906	0.1008	0.5820	0.025*
H51	1.1983	0.0662	0.0166	0.022*
H62A	0.6257	0.1049	0.2626	0.022*
H62B	0.7598	0.1279	0.1330	0.022*
H65A	0.4598	0.5291	0.3805	0.023*
H65B	0.5910	0.5352	0.2474	0.023*
H63A	0.5812	0.3748	0.0841	0.021*
H63B	0.4444	0.2504	0.0990	0.021*
H64A	0.1764	0.4345	0.1477	0.021*
H64B	0.2981	0.5693	0.1317	0.021*
H64C	0.0954	0.5037	0.3742	0.022*
H64D	0.1821	0.6559	0.3323	0.022*
H64	−0.0367	0.6977	0.1758	0.026*
H66A	0.7752	0.4075	0.4174	0.023*
H66B	0.6358	0.2857	0.4468	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0137 (6)	0.0198 (7)	0.0167 (7)	0.0008 (5)	−0.0012 (5)	−0.0006 (5)
C2	0.0144 (7)	0.0186 (8)	0.0164 (8)	0.0004 (6)	−0.0003 (6)	0.0007 (6)
N2	0.0159 (7)	0.0259 (8)	0.0175 (7)	0.0063 (6)	−0.0031 (5)	−0.0035 (6)
N3	0.0135 (6)	0.0162 (7)	0.0170 (7)	0.0003 (5)	−0.0006 (5)	0.0003 (5)
C4	0.0129 (7)	0.0150 (7)	0.0202 (8)	−0.0025 (6)	0.0014 (6)	−0.0025 (6)
Cl4	0.0182 (2)	0.0203 (2)	0.0248 (2)	0.00261 (15)	−0.00083 (15)	−0.00750 (16)
C5	0.0127 (7)	0.0153 (7)	0.0179 (8)	−0.0024 (6)	−0.0006 (6)	−0.0035 (6)
C51	0.0162 (7)	0.0207 (8)	0.0193 (8)	−0.0026 (6)	−0.0012 (6)	−0.0060 (6)
O51	0.0227 (6)	0.0308 (7)	0.0187 (6)	0.0012 (5)	−0.0037 (5)	−0.0002 (5)
C6	0.0134 (7)	0.0133 (7)	0.0179 (8)	−0.0018 (6)	−0.0004 (6)	−0.0003 (6)
N61	0.0113 (6)	0.0175 (7)	0.0174 (7)	0.0007 (5)	−0.0021 (5)	−0.0052 (5)
C62	0.0140 (7)	0.0192 (8)	0.0211 (8)	−0.0013 (6)	−0.0024 (6)	−0.0041 (6)
C65	0.0151 (7)	0.0208 (8)	0.0202 (8)	0.0031 (6)	−0.0032 (6)	−0.0070 (6)
C63	0.0153 (7)	0.0211 (8)	0.0159 (8)	−0.0026 (6)	−0.0006 (6)	−0.0040 (6)
N64	0.0115 (6)	0.0189 (7)	0.0160 (6)	0.0016 (5)	−0.0015 (5)	−0.0036 (5)
C641	0.0155 (7)	0.0200 (8)	0.0157 (7)	0.0002 (6)	−0.0023 (6)	−0.0017 (6)
C642	0.0151 (7)	0.0213 (8)	0.0159 (8)	0.0026 (6)	−0.0012 (6)	−0.0015 (6)
O64	0.0154 (6)	0.0283 (7)	0.0189 (6)	0.0057 (5)	−0.0023 (4)	−0.0012 (5)
C66	0.0149 (7)	0.0238 (8)	0.0176 (8)	0.0039 (6)	−0.0024 (6)	−0.0072 (6)

Geometric parameters (Å, º)

N1—C6	1.334 (2)	C62—H62B	0.99
N1—C2	1.338 (2)	C65—N64	1.462 (2)
C2—N2	1.325 (2)	C65—C66	1.517 (2)
C2—N3	1.379 (2)	C65—H65A	0.99
N2—H2A	0.88	C65—H65B	0.99
N2—H2B	0.88	C63—N64	1.461 (2)
N3—C4	1.300 (2)	C63—H63A	0.99
C4—C5	1.404 (2)	C63—H63B	0.99
C4—Cl4	1.7537 (16)	N64—C641	1.4663 (19)
C5—C51	1.441 (2)	C641—C642	1.520 (2)
C5—C6	1.453 (2)	C641—H64A	0.99
C51—O51	1.230 (2)	C641—H64B	0.99
C51—H51	0.95	C642—O64	1.4322 (19)
C6—N61	1.348 (2)	C642—H64C	0.99
N61—C62	1.467 (2)	C642—H64D	0.99
N61—C66	1.470 (2)	O64—H64	0.84
C62—C63	1.513 (2)	C66—H66A	0.99
C62—H62A	0.99	C66—H66B	0.99
C6—N1—C2	118.17 (14)	N64—C65—H65B	109.4
N2—C2—N1	119.01 (14)	C66—C65—H65B	109.4
N2—C2—N3	115.72 (14)	H65A—C65—H65B	108.0
N1—C2—N3	125.21 (15)	N64—C63—C62	110.64 (13)
C2—N2—H2A	120.0	N64—C63—H63A	109.5
C2—N2—H2B	120.0	C62—C63—H63A	109.5
H2A—N2—H2B	120.0	N64—C63—H63B	109.5
C4—N3—C2	113.99 (13)	C62—C63—H63B	109.5
N3—C4—C5	127.20 (15)	H63A—C63—H63B	108.1
N3—C4—Cl4	113.34 (12)	C63—N64—C65	107.16 (12)
C5—C4—Cl4	119.45 (12)	C63—N64—C641	110.50 (12)
C4—C5—C51	119.74 (14)	C65—N64—C641	112.43 (13)
C4—C5—C6	112.50 (14)	N64—C641—C642	112.68 (13)
C51—C5—C6	125.62 (14)	N64—C641—H64A	109.1
O51—C51—C5	127.38 (15)	C642—C641—H64A	109.1
O51—C51—H51	116.3	N64—C641—H64B	109.1
C5—C51—H51	116.3	C642—C641—H64B	109.1
N1—C6—N61	116.93 (14)	H64A—C641—H64B	107.8
N1—C6—C5	120.81 (14)	O64—C642—C641	111.48 (13)
N61—C6—C5	122.24 (14)	O64—C642—H64C	109.3
C6—N61—C62	121.65 (13)	C641—C642—H64C	109.3
C6—N61—C66	118.69 (13)	O64—C642—H64D	109.3
C62—N61—C66	111.99 (12)	C641—C642—H64D	109.3
N61—C62—C63	111.10 (13)	H64C—C642—H64D	108.0
N61—C62—H62A	109.4	C642—O64—H64	109.5
C63—C62—H62A	109.4	N61—C66—C65	110.30 (13)
N61—C62—H62B	109.4	N61—C66—H66A	109.6
C63—C62—H62B	109.4	C65—C66—H66A	109.6
H62A—C62—H62B	108.0	N61—C66—H66B	109.6
N64—C65—C66	111.08 (13)	C65—C66—H66B	109.6
N64—C65—H65A	109.4	H66A—C66—H66B	108.1
C66—C65—H65A	109.4
C6—N1—C2—N2	173.82 (15)	N1—C6—N61—C62	−142.52 (15)
C6—N1—C2—N3	−9.1 (2)	C5—C6—N61—C62	39.2 (2)
N2—C2—N3—C4	−169.67 (14)	N1—C6—N61—C66	4.5 (2)
N1—C2—N3—C4	13.1 (2)	C5—C6—N61—C66	−173.85 (14)
C2—N3—C4—C5	−3.0 (2)	C6—N61—C62—C63	−158.67 (14)
C2—N3—C4—Cl4	176.10 (11)	C66—N61—C62—C63	52.35 (17)
N3—C4—C5—C51	155.15 (16)	N61—C62—C63—N64	−57.80 (17)
Cl4—C4—C5—C51	−23.9 (2)	C62—C63—N64—C65	61.88 (16)
N3—C4—C5—C6	−9.2 (2)	C62—C63—N64—C641	−175.31 (13)
Cl4—C4—C5—C6	171.78 (11)	C66—C65—N64—C63	−62.39 (17)
C4—C5—C51—O51	−167.22 (16)	C66—C65—N64—C641	176.01 (13)
C6—C5—C51—O51	−5.1 (3)	C63—N64—C641—C642	176.97 (13)
C2—N1—C6—N61	176.47 (14)	C65—N64—C641—C642	−63.35 (17)
C2—N1—C6—C5	−5.2 (2)	N64—C641—C642—O64	−166.20 (13)
C4—C5—C6—N1	13.3 (2)	C6—N61—C66—C65	157.87 (14)
C51—C5—C6—N1	−149.95 (16)	C62—N61—C66—C65	−52.14 (18)
C4—C5—C6—N61	−168.45 (14)	N64—C65—C66—N61	58.05 (18)
C51—C5—C6—N61	28.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O64^i	0.88	2.03	2.909 (2)	174
N2—H2B···N3^ii	0.88	2.17	3.053 (2)	177
O64—H64···O51^iii	0.84	1.99	2.824 (2)	173

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3, −y, −z+1; (iii) −x+1, −y+1, −z.

(XII)

Crystal data

C10H13ClN4O	F(000) = 504
Mr = 240.69	Dx = 1.488 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2460 reflections
a = 14.4681 (17) Å	θ = 4.4–27.5°
b = 11.1378 (17) Å	µ = 0.34 mm^−1
c = 7.4534 (7) Å	T = 120 K
β = 116.535 (7)°	Block, colourless
V = 1074.5 (2) Å^3	0.30 × 0.26 × 0.15 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2460 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ϕ & ω scans	θmax = 27.5°, θmin = 4.4°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −18→18
Tmin = 0.896, Tmax = 0.951	k = −14→14
12891 measured reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 0.8328P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
2460 reflections	Δρmax = 0.33 e Å^−3
145 parameters	Δρmin = −0.28 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1219 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (7)

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

	x	y	z	Uiso*/Ueq
N1	0.59294 (17)	0.3488 (2)	0.4572 (3)	0.0161 (5)
N2	0.51703 (17)	0.4914 (2)	0.5696 (3)	0.0219 (5)
C2	0.6028 (2)	0.4360 (2)	0.5881 (4)	0.0173 (5)
N3	0.69313 (17)	0.47822 (19)	0.7374 (3)	0.0188 (5)
C4	0.77235 (19)	0.4102 (2)	0.7720 (4)	0.0168 (5)
Cl4	0.88693 (5)	0.45866 (5)	0.97132 (8)	0.02421 (16)
C5	0.7727 (2)	0.3043 (2)	0.6698 (4)	0.0175 (6)
C51	0.8463 (2)	0.2113 (2)	0.7736 (4)	0.0181 (5)
O51	0.83796 (14)	0.10397 (15)	0.7284 (3)	0.0214 (4)
C6	0.67916 (19)	0.2882 (2)	0.4875 (4)	0.0159 (6)
N61	0.67345 (16)	0.21224 (18)	0.3428 (3)	0.0168 (5)
C62	0.7639 (2)	0.1678 (2)	0.3234 (4)	0.0196 (6)
C63	0.7551 (2)	0.1935 (3)	0.1173 (4)	0.0247 (6)
C64	0.6546 (2)	0.1463 (3)	−0.0465 (4)	0.0271 (7)
C65	0.5642 (2)	0.2008 (3)	−0.0246 (4)	0.0249 (6)
C66	0.5741 (2)	0.1725 (2)	0.1831 (4)	0.0200 (6)
H2A	0.4565	0.4702	0.4736	0.026*
H2B	0.5211	0.5491	0.6534	0.026*
H51	0.9072	0.2348	0.8881	0.022*
H62A	0.7706	0.0802	0.3480	0.023*
H62B	0.8270	0.2068	0.4258	0.023*
H63A	0.8138	0.1557	0.1045	0.030*
H63B	0.7590	0.2813	0.1008	0.030*
H64A	0.6499	0.1671	−0.1795	0.033*
H64B	0.6525	0.0578	−0.0372	0.033*
H65A	0.4986	0.1677	−0.1284	0.030*
H65B	0.5634	0.2889	−0.0433	0.030*
H66A	0.5173	0.2125	0.1999	0.024*
H66B	0.5670	0.0848	0.1949	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0175 (11)	0.0152 (11)	0.0167 (11)	0.0006 (9)	0.0086 (9)	0.0000 (9)
N2	0.0183 (12)	0.0219 (11)	0.0214 (11)	0.0022 (9)	0.0051 (9)	−0.0075 (9)
C2	0.0164 (13)	0.0184 (14)	0.0162 (12)	−0.0011 (10)	0.0065 (11)	0.0013 (10)
N3	0.0162 (11)	0.0205 (12)	0.0165 (11)	−0.0013 (9)	0.0043 (9)	−0.0032 (9)
C4	0.0144 (13)	0.0178 (13)	0.0153 (12)	−0.0042 (10)	0.0039 (10)	0.0023 (10)
Cl4	0.0198 (3)	0.0256 (3)	0.0210 (3)	−0.0033 (3)	0.0036 (2)	−0.0050 (3)
C5	0.0170 (13)	0.0201 (13)	0.0172 (13)	0.0011 (11)	0.0094 (11)	0.0014 (11)
C51	0.0173 (13)	0.0206 (13)	0.0168 (13)	−0.0017 (11)	0.0080 (11)	−0.0002 (11)
O51	0.0209 (10)	0.0188 (10)	0.0215 (10)	0.0016 (8)	0.0067 (8)	0.0025 (8)
C6	0.0153 (13)	0.0200 (14)	0.0114 (13)	−0.0003 (11)	0.0050 (11)	0.0016 (10)
N61	0.0164 (11)	0.0177 (11)	0.0163 (10)	0.0000 (9)	0.0073 (9)	−0.0027 (9)
C62	0.0189 (14)	0.0214 (14)	0.0188 (14)	0.0017 (10)	0.0088 (12)	−0.0014 (11)
C63	0.0259 (15)	0.0292 (15)	0.0230 (15)	−0.0007 (12)	0.0144 (13)	−0.0001 (12)
C64	0.0355 (17)	0.0314 (17)	0.0173 (15)	−0.0027 (14)	0.0144 (14)	−0.0005 (13)
C65	0.0287 (16)	0.0225 (14)	0.0165 (14)	−0.0007 (13)	0.0037 (12)	−0.0004 (11)
C66	0.0178 (14)	0.0199 (13)	0.0196 (14)	−0.0014 (11)	0.0060 (11)	−0.0044 (11)

Geometric parameters (Å, º)

N1—C2	1.338 (3)	N61—C66	1.467 (3)
N1—C6	1.345 (3)	C62—C63	1.510 (4)
N2—C2	1.337 (3)	C62—H62A	0.99
N2—H2A	0.88	C62—H62B	0.99
N2—H2B	0.88	C63—C64	1.515 (4)
C2—N3	1.367 (3)	C63—H63A	0.99
N3—C4	1.300 (3)	C63—H63B	0.99
C4—C5	1.405 (4)	C64—C65	1.515 (4)
C4—Cl4	1.745 (3)	C64—H64A	0.99
C5—C6	1.438 (3)	C64—H64B	0.99
C5—C51	1.439 (4)	C65—C66	1.523 (4)
C51—O51	1.233 (3)	C65—H65A	0.99
C51—H51	0.95	C65—H65B	0.99
C6—N61	1.344 (3)	C66—H66A	0.99
N61—C62	1.466 (3)	C66—H66B	0.99
C2—N1—C6	116.9 (2)	C63—C62—H62B	109.4
C2—N2—H2A	120.0	H62A—C62—H62B	108.0
C2—N2—H2B	120.0	C62—C63—C64	111.6 (2)
H2A—N2—H2B	120.0	C62—C63—H63A	109.3
N2—C2—N1	117.9 (2)	C64—C63—H63A	109.3
N2—C2—N3	115.5 (2)	C62—C63—H63B	109.3
N1—C2—N3	126.5 (2)	C64—C63—H63B	109.3
C4—N3—C2	113.5 (2)	H63A—C63—H63B	108.0
N3—C4—C5	126.7 (2)	C65—C64—C63	109.7 (2)
N3—C4—Cl4	113.96 (19)	C65—C64—H64A	109.7
C5—C4—Cl4	119.28 (19)	C63—C64—H64A	109.7
C4—C5—C6	112.8 (2)	C65—C64—H64B	109.7
C4—C5—C51	119.6 (2)	C63—C64—H64B	109.7
C6—C5—C51	125.2 (2)	H64A—C64—H64B	108.2
O51—C51—C5	126.4 (2)	C64—C65—C66	109.4 (2)
O51—C51—H51	116.8	C64—C65—H65A	109.8
C5—C51—H51	116.8	C66—C65—H65A	109.8
N61—C6—N1	117.4 (2)	C64—C65—H65B	109.8
N61—C6—C5	122.1 (2)	C66—C65—H65B	109.8
N1—C6—C5	120.5 (2)	H65A—C65—H65B	108.2
C6—N61—C62	123.6 (2)	N61—C66—C65	112.0 (2)
C6—N61—C66	121.9 (2)	N61—C66—H66A	109.2
C62—N61—C66	114.4 (2)	C65—C66—H66A	109.2
N61—C62—C63	111.2 (2)	N61—C66—H66B	109.2
N61—C62—H62A	109.4	C65—C66—H66B	109.2
C63—C62—H62A	109.4	H66A—C66—H66B	107.9
N61—C62—H62B	109.4
C6—N1—C2—N2	−175.2 (2)	C51—C5—C6—N61	−35.6 (4)
C6—N1—C2—N3	7.2 (4)	C4—C5—C6—N1	−18.5 (3)
N2—C2—N3—C4	169.3 (2)	C51—C5—C6—N1	143.6 (3)
N1—C2—N3—C4	−13.0 (4)	N1—C6—N61—C62	161.2 (2)
C2—N3—C4—C5	1.7 (4)	C5—C6—N61—C62	−19.6 (4)
C2—N3—C4—Cl4	−176.73 (18)	N1—C6—N61—C66	−15.2 (3)
N3—C4—C5—C6	12.8 (4)	C5—C6—N61—C66	164.1 (2)
Cl4—C4—C5—C6	−168.76 (18)	C6—N61—C62—C63	−124.8 (3)
N3—C4—C5—C51	−150.4 (3)	C66—N61—C62—C63	51.8 (3)
Cl4—C4—C5—C51	28.0 (3)	N61—C62—C63—C64	−53.5 (3)
C4—C5—C51—O51	157.1 (3)	C62—C63—C64—C65	57.3 (3)
C6—C5—C51—O51	−3.9 (4)	C63—C64—C65—C66	−57.3 (3)
C2—N1—C6—N61	−171.0 (2)	C6—N61—C66—C65	123.2 (3)
C2—N1—C6—C5	9.8 (4)	C62—N61—C66—C65	−53.4 (3)
C4—C5—C6—N61	162.2 (2)	C64—C65—C66—N61	55.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O51^i	0.88	2.04	2.902 (3)	166
N2—H2B···N1^ii	0.88	2.32	3.144 (3)	155

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