3-(6-Chloro­pyridin-3-ylmeth­yl)-6-propyl-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

The title compound, C₁₃H₁₄ClN₇, crystallizes with two independent mol­ecules in the asymmetric unit, with little conformational difference between them. The triazole ring is almost coplanar with the pyrimidine ring. Intra­molecular C—H...N and inter­molecular C—H...N and N—H...N hydrogen-bonding inter­actions contribute to the stability of the structure. In addition, weak C—H...π hydrogen-bonding and strong π–π stacking inter­actions are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.185
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C12

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.32 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(6-Chloropyridin-3-ylmethyl)-6-propyl-6,7-dihydro-3H-1,2,3- triazolo[4,5-d]pyrimidin-7-imine

Crystal data

C13H14ClN7	Z = 4
Mr = 303.76	F(000) = 632
Triclinic, P1	Dx = 1.393 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1644 (9) Å	Cell parameters from 3445 reflections
b = 13.1572 (16) Å	θ = 2.6–26.7°
c = 15.6765 (19) Å	µ = 0.27 mm^−1
α = 91.008 (2)°	T = 298 K
β = 99.321 (2)°	Plate, colourless
γ = 96.281 (2)°	0.36 × 0.20 × 0.06 mm
V = 1448.5 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
φ and ω scans	h = −8→8
8283 measured reflections	k = −15→15
5029 independent reflections	l = −14→18

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0964P)^2 + 0.678P] where P = (Fo^2 + 2Fc^2)/3
5029 reflections	(Δ/σ)max < 0.001
384 parameters	Δρmax = 0.50 e Å^−3
2 restraints	Δρmin = −0.43 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
C1	0.2421 (4)	0.13915 (19)	0.22453 (18)	0.0483 (7)
C2	0.2734 (6)	0.1178 (3)	0.1419 (2)	0.0697 (9)
H2	0.3929	0.1039	0.1322	0.084*
C3	0.1252 (7)	0.1174 (3)	0.0742 (2)	0.0806 (11)
H3	0.1424	0.1038	0.0178	0.097*
C4	−0.0473 (6)	0.1373 (2)	0.0916 (2)	0.0670 (9)
C5	0.0623 (5)	0.1589 (2)	0.23316 (19)	0.0600 (8)
H5	0.0404	0.1741	0.2886	0.072*
C6	0.3969 (4)	0.1421 (2)	0.30182 (18)	0.0523 (7)
H6A	0.5129	0.1253	0.2832	0.063*
H6B	0.4213	0.2109	0.3273	0.063*
C7	0.2961 (3)	0.08996 (18)	0.44410 (16)	0.0391 (6)
C8	0.2660 (3)	−0.00361 (17)	0.47875 (16)	0.0366 (5)
C9	0.2110 (3)	−0.01297 (18)	0.56287 (16)	0.0389 (6)
C10	0.2265 (4)	0.17310 (19)	0.55525 (19)	0.0490 (7)
H10	0.2098	0.2333	0.5837	0.059*
C11	0.1423 (4)	0.0936 (2)	0.68451 (19)	0.0558 (7)
H11A	0.0629	0.1487	0.6853	0.067*
H11B	0.0662	0.0307	0.6946	0.067*
C12	0.3011 (7)	0.1122 (5)	0.7553 (3)	0.122 (2)
H12A	0.3848	0.1710	0.7425	0.146*
H12B	0.3728	0.0535	0.7588	0.146*
C13	0.2436 (7)	0.1312 (4)	0.8419 (3)	0.1106 (16)
H13A	0.1616	0.1846	0.8376	0.166*
H13B	0.3552	0.1516	0.8840	0.166*
H13C	0.1774	0.0697	0.8594	0.166*
C14	0.3600 (4)	0.62323 (19)	0.80702 (18)	0.0499 (7)
C15	0.3335 (6)	0.6294 (3)	0.8919 (2)	0.0698 (9)
H15	0.2131	0.6348	0.9054	0.084*
C16	0.4883 (7)	0.6274 (3)	0.9567 (2)	0.0821 (11)
H16	0.4752	0.6314	1.0147	0.098*
C17	0.6611 (6)	0.6194 (2)	0.9328 (2)	0.0691 (9)
C18	0.5418 (5)	0.6147 (2)	0.79213 (19)	0.0545 (7)
H18	0.5609	0.6106	0.7349	0.065*
C19	0.1959 (4)	0.6280 (2)	0.73455 (18)	0.0531 (7)
H19A	0.0776	0.6089	0.7558	0.064*
H19B	0.1953	0.6978	0.7157	0.064*
C20	0.2321 (4)	0.58421 (18)	0.58003 (17)	0.0405 (6)
C21	0.2320 (3)	0.49217 (18)	0.53819 (16)	0.0391 (6)
C22	0.2627 (4)	0.48746 (18)	0.44971 (17)	0.0413 (6)
C23	0.2789 (4)	0.6733 (2)	0.4675 (2)	0.0533 (7)
H23	0.2960	0.7353	0.4405	0.064*
C24	0.3081 (6)	0.5959 (3)	0.3272 (2)	0.0674 (9)
H24A	0.4427	0.5955	0.3253	0.081*
H24B	0.2422	0.5347	0.2958	0.081*
C25	0.2455 (8)	0.6829 (3)	0.2813 (3)	0.0998 (14)
H25A	0.3181	0.7450	0.3083	0.120*
H25B	0.1123	0.6868	0.2843	0.120*
C26	0.2719 (9)	0.6744 (4)	0.1863 (2)	0.1165 (18)
H26A	0.4039	0.6709	0.1834	0.175*
H26B	0.2307	0.7333	0.1567	0.175*
H26C	0.1977	0.6137	0.1593	0.175*
Cl1	−0.2405 (2)	0.13351 (9)	0.00703 (7)	0.1122 (5)
Cl2	0.85935 (19)	0.61704 (10)	1.01450 (7)	0.1096 (4)
N1	−0.0844 (4)	0.1579 (2)	0.16830 (18)	0.0722 (8)
N2	0.3474 (3)	0.07072 (15)	0.36722 (14)	0.0425 (5)
N3	0.3477 (3)	−0.03175 (15)	0.35419 (14)	0.0449 (5)
N4	0.2986 (3)	−0.07707 (15)	0.42239 (13)	0.0410 (5)
N5	0.1944 (3)	0.08556 (15)	0.59784 (14)	0.0441 (5)
N6	0.2776 (3)	0.18324 (15)	0.47982 (15)	0.0481 (6)
N7	0.1767 (3)	−0.09161 (16)	0.60640 (14)	0.0466 (5)
H7	0.1958	−0.1457	0.5790	0.056*
N8	0.6928 (4)	0.6118 (2)	0.85407 (18)	0.0639 (7)
N9	0.2053 (3)	0.56058 (15)	0.66061 (14)	0.0456 (5)
N10	0.1872 (4)	0.45739 (16)	0.66851 (15)	0.0526 (6)
N11	0.2049 (3)	0.41570 (15)	0.59325 (15)	0.0478 (6)
N12	0.2818 (3)	0.58796 (16)	0.41792 (14)	0.0468 (5)
N13	0.2552 (3)	0.67950 (16)	0.54768 (15)	0.0510 (6)
N14	0.2744 (4)	0.41123 (17)	0.40056 (16)	0.0534 (6)
H14	0.265 (5)	0.3553 (15)	0.4277 (18)	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0667 (18)	0.0349 (13)	0.0488 (16)	0.0113 (12)	0.0214 (13)	0.0084 (11)
C2	0.088 (3)	0.072 (2)	0.058 (2)	0.0226 (18)	0.0275 (18)	−0.0010 (16)
C3	0.129 (4)	0.077 (2)	0.0405 (18)	0.029 (2)	0.018 (2)	−0.0045 (15)
C4	0.096 (3)	0.0543 (18)	0.0498 (18)	0.0229 (17)	−0.0005 (17)	0.0035 (14)
C5	0.074 (2)	0.071 (2)	0.0397 (16)	0.0266 (16)	0.0111 (14)	0.0085 (14)
C6	0.0600 (18)	0.0438 (15)	0.0557 (17)	0.0034 (12)	0.0178 (14)	0.0121 (12)
C7	0.0369 (13)	0.0349 (12)	0.0447 (14)	0.0055 (10)	0.0034 (11)	0.0021 (10)
C8	0.0348 (13)	0.0308 (12)	0.0437 (14)	0.0052 (9)	0.0038 (10)	−0.0013 (10)
C9	0.0340 (13)	0.0361 (13)	0.0451 (14)	0.0050 (10)	0.0016 (10)	0.0000 (11)
C10	0.0533 (17)	0.0360 (14)	0.0583 (18)	0.0070 (11)	0.0103 (13)	−0.0064 (12)
C11	0.0635 (19)	0.0519 (16)	0.0537 (17)	0.0024 (13)	0.0182 (14)	−0.0088 (13)
C12	0.078 (3)	0.221 (6)	0.059 (2)	−0.005 (3)	0.011 (2)	−0.041 (3)
C13	0.126 (4)	0.142 (4)	0.062 (2)	−0.008 (3)	0.028 (3)	−0.033 (3)
C14	0.0691 (19)	0.0356 (13)	0.0476 (16)	0.0071 (12)	0.0177 (14)	−0.0047 (11)
C15	0.085 (2)	0.073 (2)	0.058 (2)	0.0175 (18)	0.0289 (18)	−0.0042 (16)
C16	0.114 (3)	0.094 (3)	0.0413 (18)	0.025 (2)	0.015 (2)	−0.0019 (17)
C17	0.087 (3)	0.0541 (18)	0.063 (2)	0.0104 (16)	0.0027 (18)	−0.0010 (15)
C18	0.073 (2)	0.0450 (15)	0.0473 (16)	0.0056 (13)	0.0164 (15)	−0.0030 (12)
C19	0.0648 (19)	0.0434 (15)	0.0541 (17)	0.0099 (13)	0.0172 (14)	−0.0085 (12)
C20	0.0400 (14)	0.0356 (13)	0.0459 (15)	0.0049 (10)	0.0076 (11)	−0.0054 (11)
C21	0.0348 (13)	0.0350 (13)	0.0465 (14)	0.0034 (10)	0.0049 (11)	−0.0040 (11)
C22	0.0392 (14)	0.0368 (13)	0.0474 (15)	0.0065 (10)	0.0049 (11)	−0.0039 (11)
C23	0.0653 (19)	0.0368 (14)	0.0594 (18)	0.0078 (12)	0.0130 (14)	0.0035 (12)
C24	0.090 (2)	0.0650 (19)	0.0539 (19)	0.0268 (17)	0.0190 (17)	0.0061 (15)
C25	0.135 (4)	0.097 (3)	0.075 (3)	0.030 (3)	0.028 (3)	0.028 (2)
C26	0.189 (5)	0.096 (3)	0.055 (2)	−0.004 (3)	0.006 (3)	0.025 (2)
Cl1	0.1476 (11)	0.1037 (8)	0.0731 (7)	0.0401 (7)	−0.0350 (7)	−0.0077 (6)
Cl2	0.1169 (10)	0.1169 (9)	0.0828 (8)	0.0198 (7)	−0.0244 (6)	0.0034 (6)
N1	0.083 (2)	0.0827 (19)	0.0542 (17)	0.0333 (15)	0.0039 (14)	0.0095 (14)
N2	0.0460 (12)	0.0349 (11)	0.0477 (13)	0.0063 (9)	0.0095 (10)	0.0062 (9)
N3	0.0496 (13)	0.0378 (11)	0.0487 (13)	0.0063 (9)	0.0116 (10)	0.0006 (9)
N4	0.0448 (12)	0.0333 (10)	0.0452 (12)	0.0060 (9)	0.0071 (9)	0.0033 (9)
N5	0.0492 (13)	0.0363 (11)	0.0473 (13)	0.0052 (9)	0.0096 (10)	−0.0038 (9)
N6	0.0558 (14)	0.0302 (11)	0.0585 (15)	0.0054 (9)	0.0098 (11)	0.0009 (10)
N7	0.0560 (14)	0.0362 (11)	0.0487 (13)	0.0047 (10)	0.0125 (11)	0.0027 (10)
N8	0.0725 (18)	0.0578 (15)	0.0606 (17)	0.0082 (13)	0.0084 (14)	−0.0007 (12)
N9	0.0537 (13)	0.0350 (11)	0.0491 (13)	0.0071 (9)	0.0106 (10)	−0.0062 (9)
N10	0.0665 (16)	0.0376 (12)	0.0553 (14)	0.0048 (10)	0.0157 (12)	−0.0030 (10)
N11	0.0580 (14)	0.0345 (11)	0.0513 (13)	0.0035 (9)	0.0116 (11)	−0.0038 (10)
N12	0.0547 (14)	0.0397 (12)	0.0472 (13)	0.0105 (10)	0.0093 (10)	−0.0006 (9)
N13	0.0643 (15)	0.0350 (12)	0.0545 (15)	0.0076 (10)	0.0118 (12)	−0.0046 (10)
N14	0.0687 (16)	0.0419 (13)	0.0515 (14)	0.0098 (11)	0.0135 (12)	−0.0051 (11)

Geometric parameters (Å, º)

C1—C5	1.369 (4)	C15—C16	1.381 (5)
C1—C2	1.379 (4)	C15—H15	0.9300
C1—C6	1.501 (4)	C16—C17	1.365 (6)
C2—C3	1.374 (5)	C16—H16	0.9300
C2—H2	0.9300	C17—N8	1.294 (4)
C3—C4	1.359 (5)	C17—Cl2	1.755 (4)
C3—H3	0.9300	C18—N8	1.336 (4)
C4—N1	1.302 (4)	C18—H18	0.9300
C4—Cl1	1.751 (4)	C19—N9	1.462 (3)
C5—N1	1.338 (4)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—N2	1.462 (3)	C20—N9	1.345 (3)
C6—H6A	0.9700	C20—N13	1.364 (3)
C6—H6B	0.9700	C20—C21	1.367 (3)
C7—N2	1.344 (3)	C21—N11	1.355 (3)
C7—C8	1.364 (3)	C21—C22	1.440 (3)
C7—N6	1.368 (3)	C22—N14	1.272 (3)
C8—N4	1.362 (3)	C22—N12	1.422 (3)
C8—C9	1.440 (3)	C23—N13	1.298 (4)
C9—N7	1.273 (3)	C23—N12	1.359 (3)
C9—N5	1.423 (3)	C23—H23	0.9300
C10—N6	1.298 (3)	C24—C25	1.438 (5)
C10—N5	1.358 (3)	C24—N12	1.468 (4)
C10—H10	0.9300	C24—H24A	0.9700
C11—C12	1.451 (5)	C24—H24B	0.9700
C11—N5	1.471 (3)	C25—C26	1.535 (6)
C11—H11A	0.9700	C25—H25A	0.9700
C11—H11B	0.9700	C25—H25B	0.9700
C12—C13	1.506 (5)	C26—H26A	0.9600
C12—H12A	0.9700	C26—H26B	0.9600
C12—H12B	0.9700	C26—H26C	0.9600
C13—H13A	0.9600	N2—N3	1.360 (3)
C13—H13B	0.9600	N3—N4	1.312 (3)
C13—H13C	0.9600	N7—H7	0.8595
C14—C18	1.376 (4)	N9—N10	1.359 (3)
C14—C15	1.377 (4)	N10—N11	1.323 (3)
C14—C19	1.505 (4)	N14—H14	0.858 (10)
C5—C1—C2	116.8 (3)	C16—C17—Cl2	118.2 (3)
C5—C1—C6	121.0 (3)	N8—C18—C14	124.6 (3)
C2—C1—C6	122.2 (3)	N8—C18—H18	117.7
C3—C2—C1	118.9 (3)	C14—C18—H18	117.7
C3—C2—H2	120.5	N9—C19—C14	112.5 (2)
C1—C2—H2	120.5	N9—C19—H19A	109.1
C4—C3—C2	118.5 (3)	C14—C19—H19A	109.1
C4—C3—H3	120.8	N9—C19—H19B	109.1
C2—C3—H3	120.8	C14—C19—H19B	109.1
N1—C4—C3	125.1 (3)	H19A—C19—H19B	107.8
N1—C4—Cl1	115.5 (3)	N9—C20—N13	127.2 (2)
C3—C4—Cl1	119.4 (3)	N9—C20—C21	104.9 (2)
N1—C5—C1	125.3 (3)	N13—C20—C21	127.8 (2)
N1—C5—H5	117.4	N11—C21—C20	109.3 (2)
C1—C5—H5	117.4	N11—C21—C22	129.9 (2)
N2—C6—C1	112.3 (2)	C20—C21—C22	120.7 (2)
N2—C6—H6A	109.1	N14—C22—N12	119.6 (2)
C1—C6—H6A	109.1	N14—C22—C21	130.7 (2)
N2—C6—H6B	109.1	N12—C22—C21	109.7 (2)
C1—C6—H6B	109.1	N13—C23—N12	128.3 (3)
H6A—C6—H6B	107.9	N13—C23—H23	115.9
N2—C7—C8	105.1 (2)	N12—C23—H23	115.9
N2—C7—N6	127.4 (2)	C25—C24—N12	117.9 (3)
C8—C7—N6	127.5 (2)	C25—C24—H24A	107.8
N4—C8—C7	109.1 (2)	N12—C24—H24A	107.8
N4—C8—C9	130.1 (2)	C25—C24—H24B	107.8
C7—C8—C9	120.9 (2)	N12—C24—H24B	107.8
N7—C9—N5	119.3 (2)	H24A—C24—H24B	107.2
N7—C9—C8	130.8 (2)	C24—C25—C26	110.5 (4)
N5—C9—C8	109.9 (2)	C24—C25—H25A	109.6
N6—C10—N5	128.1 (2)	C26—C25—H25A	109.6
N6—C10—H10	116.0	C24—C25—H25B	109.6
N5—C10—H10	116.0	C26—C25—H25B	109.6
C12—C11—N5	115.3 (3)	H25A—C25—H25B	108.1
C12—C11—H11A	108.4	C25—C26—H26A	109.5
N5—C11—H11A	108.4	C25—C26—H26B	109.5
C12—C11—H11B	108.4	H26A—C26—H26B	109.5
N5—C11—H11B	108.4	C25—C26—H26C	109.5
H11A—C11—H11B	107.5	H26A—C26—H26C	109.5
C11—C12—C13	114.1 (4)	H26B—C26—H26C	109.5
C11—C12—H12A	108.7	C4—N1—C5	115.5 (3)
C13—C12—H12A	108.7	C7—N2—N3	110.02 (19)
C11—C12—H12B	108.7	C7—N2—C6	129.4 (2)
C13—C12—H12B	108.7	N3—N2—C6	120.6 (2)
H12A—C12—H12B	107.6	N4—N3—N2	107.75 (19)
C12—C13—H13A	109.5	N3—N4—C8	108.07 (19)
C12—C13—H13B	109.5	C10—N5—C9	123.0 (2)
H13A—C13—H13B	109.5	C10—N5—C11	118.2 (2)
C12—C13—H13C	109.5	C9—N5—C11	118.8 (2)
H13A—C13—H13C	109.5	C10—N6—C7	110.7 (2)
H13B—C13—H13C	109.5	C9—N7—H7	110.0
C18—C14—C15	117.2 (3)	C17—N8—C18	115.9 (3)
C18—C14—C19	122.2 (3)	C20—N9—N10	110.2 (2)
C15—C14—C19	120.5 (3)	C20—N9—C19	129.6 (2)
C14—C15—C16	119.0 (3)	N10—N9—C19	120.1 (2)
C14—C15—H15	120.5	N11—N10—N9	107.4 (2)
C16—C15—H15	120.5	N10—N11—C21	108.1 (2)
C17—C16—C15	117.7 (3)	C23—N12—C22	123.1 (2)
C17—C16—H16	121.2	C23—N12—C24	120.6 (2)
C15—C16—H16	121.2	C22—N12—C24	116.3 (2)
N8—C17—C16	125.6 (3)	C23—N13—C20	110.4 (2)
N8—C17—Cl2	116.1 (3)	C22—N14—H14	111 (2)
C5—C1—C2—C3	−0.1 (5)	C1—C6—N2—C7	−106.0 (3)
C6—C1—C2—C3	−179.4 (3)	C1—C6—N2—N3	73.5 (3)
C1—C2—C3—C4	−0.5 (5)	C7—N2—N3—N4	−0.5 (3)
C2—C3—C4—N1	0.5 (6)	C6—N2—N3—N4	180.0 (2)
C2—C3—C4—Cl1	−178.1 (3)	N2—N3—N4—C8	0.3 (3)
C2—C1—C5—N1	0.7 (5)	C7—C8—N4—N3	0.0 (3)
C6—C1—C5—N1	−179.9 (3)	C9—C8—N4—N3	−179.2 (2)
C5—C1—C6—N2	58.0 (3)	N6—C10—N5—C9	−0.9 (4)
C2—C1—C6—N2	−122.6 (3)	N6—C10—N5—C11	178.4 (3)
N2—C7—C8—N4	−0.3 (3)	N7—C9—N5—C10	−179.3 (2)
N6—C7—C8—N4	179.6 (2)	C8—C9—N5—C10	0.2 (3)
N2—C7—C8—C9	179.0 (2)	N7—C9—N5—C11	1.5 (3)
N6—C7—C8—C9	−1.1 (4)	C8—C9—N5—C11	−179.0 (2)
N4—C8—C9—N7	−0.8 (4)	C12—C11—N5—C10	−85.9 (4)
C7—C8—C9—N7	−179.9 (3)	C12—C11—N5—C9	93.4 (4)
N4—C8—C9—N5	179.8 (2)	N5—C10—N6—C7	0.5 (4)
C7—C8—C9—N5	0.6 (3)	N2—C7—N6—C10	−179.7 (2)
N5—C11—C12—C13	173.8 (4)	C8—C7—N6—C10	0.5 (4)
C18—C14—C15—C16	0.4 (5)	C16—C17—N8—C18	1.7 (5)
C19—C14—C15—C16	−178.3 (3)	Cl2—C17—N8—C18	−179.3 (2)
C14—C15—C16—C17	0.0 (5)	C14—C18—N8—C17	−1.2 (4)
C15—C16—C17—N8	−1.2 (6)	N13—C20—N9—N10	179.7 (2)
C15—C16—C17—Cl2	179.9 (3)	C21—C20—N9—N10	−0.6 (3)
C15—C14—C18—N8	0.1 (4)	N13—C20—N9—C19	−0.8 (4)
C19—C14—C18—N8	178.9 (3)	C21—C20—N9—C19	178.9 (3)
C18—C14—C19—N9	38.1 (4)	C14—C19—N9—C20	−113.6 (3)
C15—C14—C19—N9	−143.2 (3)	C14—C19—N9—N10	65.9 (3)
N9—C20—C21—N11	0.2 (3)	C20—N9—N10—N11	0.8 (3)
N13—C20—C21—N11	179.9 (2)	C19—N9—N10—N11	−178.8 (2)
N9—C20—C21—C22	−178.3 (2)	N9—N10—N11—C21	−0.6 (3)
N13—C20—C21—C22	1.4 (4)	C20—C21—N11—N10	0.3 (3)
N11—C21—C22—N14	−0.8 (5)	C22—C21—N11—N10	178.6 (3)
C20—C21—C22—N14	177.3 (3)	N13—C23—N12—C22	−1.6 (5)
N11—C21—C22—N12	179.4 (2)	N13—C23—N12—C24	179.2 (3)
C20—C21—C22—N12	−2.5 (3)	N14—C22—N12—C23	−177.2 (3)
N12—C24—C25—C26	−176.2 (4)	C21—C22—N12—C23	2.6 (3)
C3—C4—N1—C5	0.1 (5)	N14—C22—N12—C24	2.0 (4)
Cl1—C4—N1—C5	178.7 (2)	C21—C22—N12—C24	−178.2 (2)
C1—C5—N1—C4	−0.7 (5)	C25—C24—N12—C23	−27.9 (5)
C8—C7—N2—N3	0.5 (3)	C25—C24—N12—C22	152.9 (4)
N6—C7—N2—N3	−179.4 (2)	N12—C23—N13—C20	0.2 (4)
C8—C7—N2—C6	179.9 (2)	N9—C20—N13—C23	179.6 (3)
N6—C7—N2—C6	0.1 (4)	C21—C20—N13—C23	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N4^i	0.93	2.49	3.364 (3)	157
C18—H18···N14^ii	0.93	2.62	3.511 (4)	161
C10—H10···N11	0.93	2.41	3.262 (3)	153
C5—H5···N7^iii	0.93	2.61	3.344 (4)	136
N14—H14···N6	0.86 (1)	2.43 (1)	3.268 (3)	167 (3)
N7—H7···N13^iv	0.86	2.44	3.267 (3)	162
C11—H11B···Cg1^iii	0.97	2.94	3.478 (1)	116
C24—H24A···Cg2^ii	0.97	2.96	3.792 (4)	145

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