4-Amino-6-chloro-8-p-tolyl­pteridin-7(8H)-one dichloro­methane hemisolvate

The title compound, C₁₃H₁₀ClN₅O·0.5CH₂Cl₂, crystallizes with two independent 4-amino-6-chloro-8-p-tolyl­pteridin-7(8H)-one mol­ecules and one dichloro­methane mol­ecule in the asymmetric unit. The bond lengths and angles in the mol­ecules are within normal ranges. Inter­molecular N—H...N hydrogen bonds link the two independent mol­ecules into hydrogen-bonded dimers. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.145
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C27
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C13 H10 Cl N5 O

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Amino-6-chloro-8-p-tolylpteridin-7(8H)-one dichloromethane hemisolvate

Crystal data

C13H10ClN5O·0.5CH2Cl2	F(000) = 1352
Mr = 330.18	Dx = 1.506 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb c	Cell parameters from 1528 reflections
a = 7.4644 (14) Å	θ = 2.4–22.4°
b = 16.138 (3) Å	µ = 0.45 mm^−1
c = 24.402 (5) Å	T = 298 K
β = 97.676 (3)°	Block, colourless
V = 2913.1 (10) Å^3	0.24 × 0.18 × 0.15 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	5123 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.899, Tmax = 0.935	k = −19→14
14411 measured reflections	l = −26→29

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0672P)^2 + 0.1625P] where P = (Fo^2 + 2Fc^2)/3
5123 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.32 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
Cl1	0.50437 (13)	0.24914 (6)	0.17574 (4)	0.0683 (3)
Cl2	0.01401 (13)	0.35300 (7)	0.16980 (4)	0.0689 (3)
Cl3	0.83601 (18)	0.92666 (13)	0.46429 (7)	0.1526 (7)
Cl4	0.45459 (17)	0.92713 (10)	0.42933 (5)	0.1146 (5)
O1	0.6735 (3)	0.26461 (14)	0.29114 (9)	0.0580 (7)
O2	0.1615 (3)	0.34698 (15)	0.28728 (9)	0.0574 (6)
N1	0.4519 (3)	0.20083 (15)	0.33138 (9)	0.0383 (6)
N2	0.2610 (3)	0.17828 (16)	0.22621 (10)	0.0425 (6)
N3	−0.0385 (3)	0.08222 (16)	0.31353 (11)	0.0493 (7)
N4	0.2270 (3)	0.13060 (16)	0.37118 (10)	0.0457 (7)
N5	−0.0752 (4)	0.10424 (18)	0.21943 (11)	0.0592 (8)
H5B	−0.1783	0.0797	0.2167	0.071*
H5C	−0.0363	0.1234	0.1903	0.071*
N6	−0.0721 (3)	0.41235 (15)	0.32089 (10)	0.0376 (6)
N7	−0.2438 (3)	0.42520 (15)	0.21243 (10)	0.0412 (6)
N8	−0.5708 (3)	0.52221 (17)	0.29016 (11)	0.0486 (7)
N9	−0.3144 (3)	0.47896 (17)	0.35377 (10)	0.0480 (7)
N10	−0.5861 (4)	0.49876 (18)	0.19714 (10)	0.0556 (8)
H10A	−0.6902	0.5225	0.1926	0.067*
H10B	−0.5410	0.4797	0.1690	0.067*
C1	0.5284 (4)	0.23031 (19)	0.28627 (13)	0.0417 (8)
C2	0.4147 (4)	0.21365 (19)	0.23294 (12)	0.0422 (8)
C3	0.1948 (4)	0.15071 (18)	0.27302 (12)	0.0381 (7)
C4	0.0246 (4)	0.11251 (19)	0.26881 (13)	0.0419 (8)
C5	0.0689 (4)	0.0930 (2)	0.36085 (14)	0.0513 (9)
H5A	0.0259	0.0706	0.3917	0.062*
C6	0.2876 (4)	0.16013 (18)	0.32552 (12)	0.0396 (7)
C7	0.5428 (4)	0.2214 (2)	0.38608 (12)	0.0391 (7)
C8	0.5209 (4)	0.2988 (2)	0.40632 (13)	0.0481 (8)
H8B	0.4508	0.3376	0.3850	0.058*
C9	0.6023 (4)	0.3195 (2)	0.45828 (14)	0.0559 (9)
H9B	0.5878	0.3726	0.4718	0.067*
C10	0.7061 (5)	0.2620 (3)	0.49105 (14)	0.0564 (10)
C11	0.7283 (5)	0.1843 (3)	0.46889 (14)	0.0588 (10)
H11A	0.7989	0.1452	0.4898	0.071*
C12	0.6483 (4)	0.1635 (2)	0.41664 (13)	0.0504 (9)
H12A	0.6653	0.1112	0.4022	0.060*
C13	0.7890 (6)	0.2838 (3)	0.54866 (15)	0.0850 (13)
H13A	0.8858	0.2460	0.5605	0.127*
H13B	0.6988	0.2800	0.5732	0.127*
H13C	0.8353	0.3393	0.5492	0.127*
C14	0.0148 (4)	0.37972 (19)	0.27917 (13)	0.0430 (8)
C15	−0.0904 (4)	0.39132 (19)	0.22330 (12)	0.0415 (8)
C16	−0.3230 (4)	0.45446 (18)	0.25646 (12)	0.0360 (7)
C17	−0.4951 (4)	0.49155 (19)	0.24749 (12)	0.0409 (8)
C18	−0.4745 (4)	0.5132 (2)	0.33982 (14)	0.0538 (9)
H18A	−0.5283	0.5343	0.3691	0.065*
C19	−0.2401 (4)	0.44936 (18)	0.31064 (12)	0.0375 (7)
C20	0.0147 (4)	0.4017 (2)	0.37723 (12)	0.0399 (7)
C21	0.0879 (5)	0.4679 (2)	0.40728 (14)	0.0593 (10)
H21A	0.0839	0.5205	0.3916	0.071*
C22	0.1673 (5)	0.4563 (3)	0.46083 (15)	0.0682 (11)
H22A	0.2151	0.5017	0.4813	0.082*
C23	0.1778 (5)	0.3788 (3)	0.48496 (14)	0.0607 (10)
C24	0.1048 (4)	0.3132 (2)	0.45350 (14)	0.0575 (9)
H24A	0.1109	0.2603	0.4688	0.069*
C25	0.0228 (4)	0.3241 (2)	0.39988 (12)	0.0453 (8)
H25A	−0.0265	0.2790	0.3794	0.054*
C26	0.2654 (6)	0.3665 (3)	0.54384 (14)	0.0915 (16)
H26A	0.2587	0.3091	0.5536	0.137*
H26B	0.2034	0.3993	0.5682	0.137*
H26C	0.3897	0.3833	0.5471	0.137*
C27	0.6316 (6)	0.8908 (3)	0.4762 (2)	0.1137 (18)
H27A	0.6114	0.9070	0.5132	0.136*
H27B	0.6326	0.8308	0.4748	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0739 (7)	0.0861 (8)	0.0460 (5)	−0.0283 (5)	0.0127 (4)	0.0014 (5)
Cl2	0.0648 (6)	0.0900 (8)	0.0528 (6)	0.0192 (5)	0.0107 (4)	−0.0140 (5)
Cl3	0.0767 (9)	0.2105 (19)	0.1740 (15)	0.0068 (10)	0.0285 (9)	0.0752 (13)
Cl4	0.0883 (9)	0.1710 (14)	0.0836 (8)	−0.0010 (9)	0.0081 (7)	0.0404 (8)
O1	0.0473 (14)	0.0700 (17)	0.0562 (14)	−0.0279 (13)	0.0046 (11)	0.0028 (12)
O2	0.0445 (14)	0.0702 (17)	0.0559 (14)	0.0216 (12)	0.0006 (11)	−0.0080 (12)
N1	0.0338 (14)	0.0427 (16)	0.0381 (14)	−0.0072 (12)	0.0032 (11)	0.0001 (12)
N2	0.0402 (15)	0.0383 (15)	0.0484 (16)	−0.0028 (13)	0.0035 (12)	−0.0068 (12)
N3	0.0382 (15)	0.0485 (18)	0.0606 (19)	−0.0087 (13)	0.0045 (14)	−0.0023 (14)
N4	0.0366 (15)	0.0498 (17)	0.0505 (16)	−0.0082 (13)	0.0055 (12)	0.0014 (13)
N5	0.0399 (16)	0.079 (2)	0.0574 (18)	−0.0191 (15)	0.0010 (14)	−0.0101 (16)
N6	0.0301 (13)	0.0364 (15)	0.0445 (15)	0.0043 (11)	−0.0017 (11)	−0.0026 (12)
N7	0.0396 (15)	0.0390 (15)	0.0437 (15)	−0.0029 (12)	0.0007 (12)	0.0002 (12)
N8	0.0338 (14)	0.0575 (18)	0.0518 (17)	0.0081 (13)	−0.0042 (13)	−0.0011 (14)
N9	0.0366 (15)	0.0591 (18)	0.0470 (16)	0.0088 (13)	−0.0002 (12)	−0.0062 (14)
N10	0.0415 (16)	0.075 (2)	0.0471 (17)	0.0142 (15)	−0.0042 (13)	0.0072 (15)
C1	0.0407 (19)	0.0352 (18)	0.049 (2)	−0.0041 (15)	0.0042 (15)	−0.0003 (15)
C2	0.046 (2)	0.0394 (18)	0.0415 (18)	−0.0030 (16)	0.0058 (15)	−0.0040 (15)
C3	0.0323 (17)	0.0360 (18)	0.0458 (19)	0.0000 (14)	0.0041 (14)	−0.0061 (14)
C4	0.0327 (17)	0.0378 (18)	0.054 (2)	0.0011 (14)	0.0018 (16)	−0.0075 (16)
C5	0.044 (2)	0.056 (2)	0.055 (2)	−0.0089 (17)	0.0113 (17)	0.0010 (18)
C6	0.0333 (17)	0.0368 (18)	0.0490 (19)	0.0005 (14)	0.0062 (15)	−0.0017 (15)
C7	0.0318 (17)	0.0424 (19)	0.0428 (18)	−0.0080 (15)	0.0035 (14)	−0.0007 (15)
C8	0.0423 (19)	0.052 (2)	0.048 (2)	−0.0002 (16)	−0.0037 (15)	−0.0017 (17)
C9	0.053 (2)	0.058 (2)	0.056 (2)	−0.0059 (19)	0.0019 (18)	−0.0102 (19)
C10	0.044 (2)	0.082 (3)	0.042 (2)	−0.014 (2)	0.0021 (16)	−0.002 (2)
C11	0.052 (2)	0.069 (3)	0.052 (2)	0.003 (2)	−0.0029 (17)	0.014 (2)
C12	0.048 (2)	0.050 (2)	0.051 (2)	0.0014 (17)	−0.0007 (16)	0.0035 (17)
C13	0.079 (3)	0.119 (4)	0.053 (2)	−0.019 (3)	−0.004 (2)	−0.002 (2)
C14	0.0385 (19)	0.0403 (19)	0.050 (2)	0.0039 (15)	0.0050 (15)	0.0015 (15)
C15	0.0405 (19)	0.0396 (19)	0.0440 (18)	0.0039 (15)	0.0042 (15)	−0.0028 (14)
C16	0.0295 (16)	0.0341 (17)	0.0429 (18)	0.0001 (13)	−0.0007 (13)	0.0013 (14)
C17	0.0352 (18)	0.0385 (19)	0.048 (2)	−0.0019 (14)	0.0013 (15)	0.0061 (15)
C18	0.042 (2)	0.064 (2)	0.055 (2)	0.0118 (18)	0.0057 (17)	−0.0071 (18)
C19	0.0319 (17)	0.0319 (17)	0.0479 (19)	−0.0005 (14)	0.0026 (14)	−0.0025 (14)
C20	0.0303 (16)	0.046 (2)	0.0414 (18)	0.0060 (15)	−0.0023 (13)	−0.0062 (16)
C21	0.061 (2)	0.048 (2)	0.063 (2)	0.0012 (18)	−0.0115 (19)	−0.0108 (18)
C22	0.063 (2)	0.069 (3)	0.065 (3)	0.003 (2)	−0.016 (2)	−0.023 (2)
C23	0.045 (2)	0.088 (3)	0.045 (2)	0.015 (2)	−0.0069 (16)	−0.011 (2)
C24	0.052 (2)	0.065 (3)	0.053 (2)	0.0113 (19)	−0.0021 (17)	0.0046 (19)
C25	0.0400 (18)	0.051 (2)	0.0430 (19)	0.0016 (16)	−0.0026 (15)	−0.0040 (16)
C26	0.078 (3)	0.141 (4)	0.048 (2)	0.028 (3)	−0.017 (2)	−0.016 (2)
C27	0.093 (4)	0.124 (4)	0.123 (4)	0.005 (3)	0.009 (3)	0.043 (4)

Geometric parameters (Å, º)

Cl1—C2	1.724 (3)	C7—C8	1.361 (4)
Cl2—C15	1.722 (3)	C7—C12	1.376 (4)
Cl3—C27	1.693 (5)	C8—C9	1.372 (4)
Cl4—C27	1.730 (5)	C8—H8B	0.9300
O1—C1	1.208 (3)	C9—C10	1.391 (5)
O2—C14	1.208 (3)	C9—H9B	0.9300
N1—C6	1.382 (4)	C10—C11	1.385 (5)
N1—C1	1.390 (4)	C10—C13	1.500 (5)
N1—C7	1.453 (3)	C11—C12	1.375 (4)
N2—C2	1.272 (4)	C11—H11A	0.9300
N2—C3	1.378 (4)	C12—H12A	0.9300
N3—C5	1.326 (4)	C13—H13A	0.9600
N3—C4	1.337 (4)	C13—H13B	0.9600
N4—C5	1.321 (4)	C13—H13C	0.9600
N4—C6	1.344 (4)	C14—C15	1.492 (4)
N5—C4	1.336 (4)	C16—C19	1.385 (4)
N5—H5B	0.8600	C16—C17	1.408 (4)
N5—H5C	0.8600	C18—H18A	0.9300
N6—C19	1.381 (3)	C20—C21	1.368 (4)
N6—C14	1.382 (4)	C20—C25	1.368 (4)
N6—C20	1.450 (4)	C21—C22	1.374 (5)
N7—C15	1.264 (4)	C21—H21A	0.9300
N7—C16	1.377 (4)	C22—C23	1.380 (5)
N8—C18	1.332 (4)	C22—H22A	0.9300
N8—C17	1.344 (4)	C23—C24	1.377 (5)
N9—C18	1.319 (4)	C23—C26	1.510 (5)
N9—C19	1.341 (4)	C24—C25	1.379 (4)
N10—C17	1.327 (3)	C24—H24A	0.9300
N10—H10A	0.8600	C25—H25A	0.9300
N10—H10B	0.8600	C26—H26A	0.9600
C1—C2	1.480 (4)	C26—H26B	0.9600
C3—C6	1.381 (4)	C26—H26C	0.9600
C3—C4	1.404 (4)	C27—H27A	0.9700
C5—H5A	0.9300	C27—H27B	0.9700
C6—N1—C1	122.2 (2)	C10—C13—H13A	109.5
C6—N1—C7	120.2 (2)	C10—C13—H13B	109.5
C1—N1—C7	117.3 (2)	H13A—C13—H13B	109.5
C2—N2—C3	117.1 (3)	C10—C13—H13C	109.5
C5—N3—C4	115.1 (3)	H13A—C13—H13C	109.5
C5—N4—C6	113.3 (3)	H13B—C13—H13C	109.5
C4—N5—H5B	120.0	O2—C14—N6	123.4 (3)
C4—N5—H5C	120.0	O2—C14—C15	124.0 (3)
H5B—N5—H5C	120.0	N6—C14—C15	112.6 (3)
C19—N6—C14	122.4 (2)	N7—C15—C14	126.7 (3)
C19—N6—C20	120.2 (2)	N7—C15—Cl2	119.0 (2)
C14—N6—C20	117.3 (2)	C14—C15—Cl2	114.3 (2)
C15—N7—C16	117.1 (2)	N7—C16—C19	122.7 (3)
C18—N8—C17	115.7 (3)	N7—C16—C17	120.2 (3)
C18—N9—C19	113.7 (3)	C19—C16—C17	117.1 (3)
C17—N10—H10A	120.0	N10—C17—N8	118.0 (3)
C17—N10—H10B	120.0	N10—C17—C16	121.7 (3)
H10A—N10—H10B	120.0	N8—C17—C16	120.4 (3)
O1—C1—N1	122.4 (3)	N9—C18—N8	129.8 (3)
O1—C1—C2	124.8 (3)	N9—C18—H18A	115.1
N1—C1—C2	112.7 (3)	N8—C18—H18A	115.1
N2—C2—C1	126.6 (3)	N9—C19—N6	118.2 (3)
N2—C2—Cl1	119.0 (2)	N9—C19—C16	123.3 (3)
C1—C2—Cl1	114.4 (2)	N6—C19—C16	118.5 (3)
N2—C3—C6	122.9 (3)	C21—C20—C25	120.4 (3)
N2—C3—C4	120.2 (3)	C21—C20—N6	120.8 (3)
C6—C3—C4	116.9 (3)	C25—C20—N6	118.8 (3)
N5—C4—N3	119.0 (3)	C20—C21—C22	119.6 (3)
N5—C4—C3	120.0 (3)	C20—C21—H21A	120.2
N3—C4—C3	121.0 (3)	C22—C21—H21A	120.2
N4—C5—N3	130.3 (3)	C21—C22—C23	121.5 (3)
N4—C5—H5A	114.8	C21—C22—H22A	119.3
N3—C5—H5A	114.8	C23—C22—H22A	119.3
N4—C6—C3	123.2 (3)	C24—C23—C22	117.6 (3)
N4—C6—N1	118.3 (3)	C24—C23—C26	121.2 (4)
C3—C6—N1	118.5 (3)	C22—C23—C26	121.2 (4)
C8—C7—C12	121.0 (3)	C23—C24—C25	121.6 (4)
C8—C7—N1	118.7 (3)	C23—C24—H24A	119.2
C12—C7—N1	120.4 (3)	C25—C24—H24A	119.2
C7—C8—C9	119.9 (3)	C20—C25—C24	119.3 (3)
C7—C8—H8B	120.0	C20—C25—H25A	120.3
C9—C8—H8B	120.0	C24—C25—H25A	120.3
C8—C9—C10	120.9 (3)	C23—C26—H26A	109.5
C8—C9—H9B	119.5	C23—C26—H26B	109.5
C10—C9—H9B	119.5	H26A—C26—H26B	109.5
C11—C10—C9	117.8 (3)	C23—C26—H26C	109.5
C11—C10—C13	121.5 (4)	H26A—C26—H26C	109.5
C9—C10—C13	120.8 (4)	H26B—C26—H26C	109.5
C12—C11—C10	121.6 (3)	Cl3—C27—Cl4	113.4 (3)
C12—C11—H11A	119.2	Cl3—C27—H27A	108.9
C10—C11—H11A	119.2	Cl4—C27—H27A	108.9
C11—C12—C7	118.9 (3)	Cl3—C27—H27B	108.9
C11—C12—H12A	120.6	Cl4—C27—H27B	108.9
C7—C12—H12A	120.6	H27A—C27—H27B	107.7
C6—N1—C1—O1	−178.7 (3)	C19—N6—C14—O2	−179.9 (3)
C7—N1—C1—O1	7.3 (4)	C20—N6—C14—O2	−3.7 (4)
C6—N1—C1—C2	0.4 (4)	C19—N6—C14—C15	1.5 (4)
C7—N1—C1—C2	−173.7 (2)	C20—N6—C14—C15	177.7 (2)
C3—N2—C2—C1	−1.7 (5)	C16—N7—C15—C14	−0.1 (5)
C3—N2—C2—Cl1	179.8 (2)	C16—N7—C15—Cl2	179.6 (2)
O1—C1—C2—N2	−179.5 (3)	O2—C14—C15—N7	−179.8 (3)
N1—C1—C2—N2	1.5 (5)	N6—C14—C15—N7	−1.2 (5)
O1—C1—C2—Cl1	−1.0 (4)	O2—C14—C15—Cl2	0.5 (4)
N1—C1—C2—Cl1	−180.0 (2)	N6—C14—C15—Cl2	179.1 (2)
C2—N2—C3—C6	0.1 (4)	C15—N7—C16—C19	1.2 (4)
C2—N2—C3—C4	178.8 (3)	C15—N7—C16—C17	−178.9 (3)
C5—N3—C4—N5	180.0 (3)	C18—N8—C17—N10	179.8 (3)
C5—N3—C4—C3	1.6 (4)	C18—N8—C17—C16	−1.4 (4)
N2—C3—C4—N5	−1.3 (4)	N7—C16—C17—N10	0.6 (4)
C6—C3—C4—N5	177.5 (3)	C19—C16—C17—N10	−179.5 (3)
N2—C3—C4—N3	177.1 (3)	N7—C16—C17—N8	−178.2 (3)
C6—C3—C4—N3	−4.1 (4)	C19—C16—C17—N8	1.7 (4)
C6—N4—C5—N3	−1.9 (5)	C19—N9—C18—N8	0.2 (5)
C4—N3—C5—N4	1.6 (5)	C17—N8—C18—N9	0.4 (5)
C5—N4—C6—C3	−1.1 (4)	C18—N9—C19—N6	179.9 (3)
C5—N4—C6—N1	179.9 (3)	C18—N9—C19—C16	0.2 (4)
N2—C3—C6—N4	−177.4 (3)	C14—N6—C19—N9	179.7 (3)
C4—C3—C6—N4	3.8 (4)	C20—N6—C19—N9	3.7 (4)
N2—C3—C6—N1	1.6 (4)	C14—N6—C19—C16	−0.6 (4)
C4—C3—C6—N1	−177.1 (3)	C20—N6—C19—C16	−176.6 (3)
C1—N1—C6—N4	177.3 (3)	N7—C16—C19—N9	178.8 (3)
C7—N1—C6—N4	−8.8 (4)	C17—C16—C19—N9	−1.1 (4)
C1—N1—C6—C3	−1.8 (4)	N7—C16—C19—N6	−0.9 (4)
C7—N1—C6—C3	172.1 (3)	C17—C16—C19—N6	179.2 (3)
C6—N1—C7—C8	−96.4 (3)	C19—N6—C20—C21	−73.5 (4)
C1—N1—C7—C8	77.8 (3)	C14—N6—C20—C21	110.3 (3)
C6—N1—C7—C12	83.5 (4)	C19—N6—C20—C25	106.7 (3)
C1—N1—C7—C12	−102.4 (3)	C14—N6—C20—C25	−69.5 (4)
C12—C7—C8—C9	−1.1 (5)	C25—C20—C21—C22	−1.0 (5)
N1—C7—C8—C9	178.8 (3)	N6—C20—C21—C22	179.2 (3)
C7—C8—C9—C10	−0.6 (5)	C20—C21—C22—C23	1.0 (6)
C8—C9—C10—C11	1.7 (5)	C21—C22—C23—C24	−0.3 (6)
C8—C9—C10—C13	−177.6 (3)	C21—C22—C23—C26	180.0 (4)
C9—C10—C11—C12	−1.1 (5)	C22—C23—C24—C25	−0.4 (5)
C13—C10—C11—C12	178.2 (3)	C26—C23—C24—C25	179.3 (3)
C10—C11—C12—C7	−0.6 (5)	C21—C20—C25—C24	0.3 (5)
C8—C7—C12—C11	1.7 (5)	N6—C20—C25—C24	−179.9 (3)
N1—C7—C12—C11	−178.2 (3)	C23—C24—C25—C20	0.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···N8^i	0.86	2.08	2.937 (4)	179
N10—H10A···N3^ii	0.86	2.23	3.089 (4)	176

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