5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetra-hydro-pyrrolo-[3,4-c]pyrazole-1,5-dicarboxyl-ate.

The asymmetric unit of the title compound, C(13)H(20)N(4)O(4), contains two crystallographically independent mol-ecules in which the dihedral angles between the fused pyrrole and pyrazole rings are 5.06 (8) and 1.12 (8)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and N-H⋯N hydrogen bonds into chains parallel to the b axis.

Related literature

For general background to potential anti­cancer kinase inhibitors, see: Fancelli et al. (2005 ▶); Gadekar et al. (1968 ▶). For the structure of a related compound synthesized by our group, see: Guo et al. (2010 ▶).

Experimental

Crystal data

C13H20N4O4

M = 296.33

Triclinic,

a = 10.772 (3) Å

b = 12.180 (4) Å

c = 12.986 (4) Å

α = 70.845 (5)°

β = 65.875 (4)°

γ = 85.821 (5)°

V = 1465.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.06 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.994, T max = 0.996

7444 measured reflections

5102 independent reflections

3915 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.03

5102 reflections

387 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013444/rz2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013444/rz2580Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H20N4O4	Z = 4
Mr = 296.33	F(000) = 632
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.772 (3) Å	Cell parameters from 2737 reflections
b = 12.180 (4) Å	θ = 2.6–28.0°
c = 12.986 (4) Å	µ = 0.10 mm−1
α = 70.845 (5)°	T = 296 K
β = 65.875 (4)°	Block, colourless
γ = 85.821 (5)°	0.06 × 0.05 × 0.04 mm
V = 1465.2 (7) Å3

Bruker APEXII CCD diffractometer	5102 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→10
Tmin = 0.994, Tmax = 0.996	k = −12→14
7444 measured reflections	l = −15→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.4323P] where P = (Fo2 + 2Fc2)/3
5102 reflections	(Δ/σ)max < 0.001
387 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.26829 (15)	0.40073 (13)	0.06447 (14)	0.0348 (4)
O2	0.15420 (17)	0.22918 (13)	0.11483 (14)	0.0383 (4)
O3	0.18836 (13)	0.80172 (12)	0.11637 (12)	0.0248 (3)
O4	−0.02679 (14)	0.86224 (13)	0.15737 (14)	0.0303 (4)
O5	0.28280 (14)	1.06702 (13)	0.45631 (14)	0.0333 (4)
O6	0.39625 (15)	1.23659 (13)	0.41233 (14)	0.0348 (4)
O7	0.33735 (13)	0.66947 (12)	0.40945 (12)	0.0263 (3)
O8	0.54850 (14)	0.63169 (12)	0.29063 (12)	0.0264 (3)
N1	0.04383 (17)	0.39313 (15)	0.13325 (15)	0.0266 (4)
N2	−0.08554 (17)	0.34058 (15)	0.17464 (16)	0.0278 (4)
N3	0.03062 (16)	0.69338 (14)	0.12056 (15)	0.0252 (4)
N4	−0.30512 (18)	0.40713 (16)	0.22648 (17)	0.0334 (5)
H4"	−0.3627	0.4607	0.2482	0.050*
H4'	−0.3438	0.3339	0.2641	0.050*
N5	0.50579 (16)	1.08232 (14)	0.36264 (15)	0.0240 (4)
N6	0.63493 (17)	1.14050 (15)	0.30111 (15)	0.0259 (4)
N7	0.51226 (16)	0.79033 (14)	0.34994 (15)	0.0238 (4)
N8	0.85181 (18)	1.08823 (16)	0.19749 (17)	0.0363 (5)
H8'	0.8873	1.1559	0.1818	0.044*
H8"	0.9026	1.0366	0.1726	0.044*
C1	0.0358 (2)	0.50843 (17)	0.12258 (17)	0.0240 (5)
C2	−0.1695 (2)	0.42522 (18)	0.18909 (18)	0.0265 (5)
C3	−0.0945 (2)	0.53222 (18)	0.15632 (18)	0.0239 (5)
C4	−0.1110 (2)	0.65547 (17)	0.15288 (19)	0.0252 (5)
H4D	−0.1435	0.6998	0.0929	0.030*
H4E	−0.1721	0.6611	0.2300	0.030*
C5	0.1312 (2)	0.60819 (17)	0.08967 (18)	0.0247 (5)
H5A	0.1848	0.5907	0.1369	0.030*
H5B	0.1914	0.6337	0.0054	0.030*
C6	0.1580 (2)	0.33069 (19)	0.10486 (18)	0.0289 (5)
C7	0.3986 (2)	0.3522 (2)	0.0194 (2)	0.0403 (6)
H7A	0.4667	0.4144	−0.0399	0.048*
H7B	0.3917	0.2983	−0.0191	0.048*
C8	0.4422 (3)	0.2901 (3)	0.1178 (2)	0.0500 (7)
H8D	0.4388	0.3408	0.1619	0.075*
H8E	0.5337	0.2679	0.0845	0.075*
H8F	0.3822	0.2218	0.1703	0.075*
C9	0.0578 (2)	0.79265 (17)	0.13261 (18)	0.0233 (5)
C10	0.24457 (19)	0.90541 (17)	0.12164 (18)	0.0230 (5)
C11	0.3866 (2)	0.87316 (18)	0.10925 (19)	0.0286 (5)
H11A	0.3815	0.8011	0.1707	0.043*
H11B	0.4315	0.9335	0.1168	0.043*
H11C	0.4371	0.8643	0.0324	0.043*
C12	0.1652 (2)	0.9233 (2)	0.24050 (18)	0.0303 (5)
H12A	0.0756	0.9455	0.2468	0.046*
H12B	0.2116	0.9837	0.2466	0.046*
H12C	0.1577	0.8522	0.3038	0.046*
C13	0.2481 (2)	1.00881 (18)	0.01703 (18)	0.0279 (5)
H13A	0.2999	0.9927	−0.0559	0.042*
H13B	0.2899	1.0760	0.0166	0.042*
H13C	0.1567	1.0235	0.0239	0.042*
C14	0.7175 (2)	1.06333 (17)	0.26074 (18)	0.0242 (5)
C15	0.6416 (2)	0.95619 (17)	0.29503 (17)	0.0223 (4)
C16	0.5126 (2)	0.97181 (17)	0.35743 (17)	0.0226 (4)
C17	0.3930 (2)	1.13870 (19)	0.41168 (18)	0.0272 (5)
C18	0.1527 (2)	1.1110 (2)	0.5106 (2)	0.0393 (6)
H18A	0.1624	1.1630	0.5500	0.047*
H18B	0.0880	1.0467	0.5704	0.047*
C19	0.0999 (3)	1.1747 (3)	0.4194 (2)	0.0500 (7)
H19A	0.1563	1.2452	0.3675	0.075*
H19B	0.0080	1.1935	0.4585	0.075*
H19C	0.1014	1.1266	0.3734	0.075*
C20	0.4166 (2)	0.86791 (17)	0.40609 (18)	0.0245 (5)
H20A	0.3799	0.8369	0.4926	0.029*
H20B	0.3426	0.8839	0.3802	0.029*
C21	0.65594 (19)	0.83642 (17)	0.28762 (18)	0.0227 (4)
H21A	0.6951	0.8374	0.2055	0.027*
H21B	0.7108	0.7922	0.3283	0.027*
C22	0.4724 (2)	0.69102 (17)	0.34557 (17)	0.0223 (4)
C23	0.2682 (2)	0.55632 (18)	0.43977 (19)	0.0269 (5)
C24	0.3325 (2)	0.45964 (18)	0.5035 (2)	0.0318 (5)
H24A	0.4243	0.4547	0.4499	0.048*
H24B	0.2809	0.3872	0.5303	0.048*
H24C	0.3335	0.4753	0.5710	0.048*
C25	0.2688 (2)	0.5414 (2)	0.3285 (2)	0.0366 (6)
H25A	0.2313	0.6073	0.2891	0.055*
H25B	0.2148	0.4717	0.3500	0.055*
H25C	0.3607	0.5358	0.2756	0.055*
C26	0.1261 (2)	0.5688 (2)	0.5249 (2)	0.0355 (6)
H26A	0.1310	0.5911	0.5876	0.053*
H26B	0.0732	0.4958	0.5588	0.053*
H26C	0.0837	0.6274	0.4825	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (8)	0.0283 (9)	0.0448 (9)	0.0079 (7)	−0.0123 (7)	−0.0166 (7)
O2	0.0497 (10)	0.0235 (9)	0.0474 (10)	0.0099 (7)	−0.0223 (8)	−0.0171 (7)
O3	0.0228 (7)	0.0174 (7)	0.0364 (8)	0.0017 (6)	−0.0129 (6)	−0.0105 (6)
O4	0.0246 (8)	0.0212 (8)	0.0471 (9)	0.0035 (6)	−0.0139 (7)	−0.0151 (7)
O5	0.0252 (8)	0.0301 (9)	0.0415 (9)	0.0043 (7)	−0.0074 (7)	−0.0165 (7)
O6	0.0394 (9)	0.0243 (9)	0.0429 (9)	0.0074 (7)	−0.0140 (7)	−0.0184 (7)
O7	0.0257 (8)	0.0195 (8)	0.0348 (8)	−0.0016 (6)	−0.0130 (6)	−0.0089 (6)
O8	0.0308 (8)	0.0185 (8)	0.0308 (8)	0.0028 (6)	−0.0126 (6)	−0.0094 (6)
N1	0.0303 (9)	0.0179 (9)	0.0328 (10)	0.0031 (7)	−0.0125 (8)	−0.0106 (8)
N2	0.0319 (10)	0.0197 (9)	0.0331 (10)	0.0011 (8)	−0.0137 (8)	−0.0096 (8)
N3	0.0234 (9)	0.0187 (9)	0.0354 (10)	0.0032 (7)	−0.0120 (8)	−0.0115 (8)
N4	0.0298 (10)	0.0221 (10)	0.0455 (11)	−0.0031 (8)	−0.0124 (9)	−0.0103 (9)
N5	0.0252 (9)	0.0170 (9)	0.0291 (9)	0.0010 (7)	−0.0101 (7)	−0.0081 (7)
N6	0.0258 (9)	0.0191 (9)	0.0313 (10)	0.0001 (7)	−0.0100 (8)	−0.0083 (8)
N7	0.0241 (9)	0.0186 (9)	0.0309 (9)	0.0018 (7)	−0.0117 (7)	−0.0103 (7)
N8	0.0266 (10)	0.0200 (10)	0.0557 (13)	−0.0013 (8)	−0.0077 (9)	−0.0156 (9)
C1	0.0319 (11)	0.0191 (11)	0.0244 (10)	0.0021 (9)	−0.0134 (9)	−0.0088 (9)
C2	0.0340 (12)	0.0213 (11)	0.0256 (11)	−0.0009 (9)	−0.0134 (9)	−0.0070 (9)
C3	0.0274 (11)	0.0205 (11)	0.0269 (11)	0.0030 (9)	−0.0128 (9)	−0.0096 (9)
C4	0.0264 (11)	0.0188 (11)	0.0325 (11)	0.0003 (8)	−0.0133 (9)	−0.0090 (9)
C5	0.0267 (11)	0.0209 (11)	0.0290 (11)	0.0040 (9)	−0.0116 (9)	−0.0113 (9)
C6	0.0391 (13)	0.0229 (12)	0.0278 (11)	0.0068 (10)	−0.0148 (10)	−0.0116 (9)
C7	0.0344 (13)	0.0409 (15)	0.0446 (14)	0.0137 (11)	−0.0116 (11)	−0.0210 (12)
C8	0.0479 (15)	0.0555 (18)	0.0545 (17)	0.0147 (13)	−0.0253 (13)	−0.0244 (14)
C9	0.0248 (10)	0.0175 (10)	0.0254 (10)	−0.0007 (9)	−0.0097 (9)	−0.0047 (8)
C10	0.0221 (10)	0.0180 (10)	0.0280 (11)	−0.0034 (8)	−0.0092 (8)	−0.0068 (8)
C11	0.0268 (11)	0.0234 (11)	0.0346 (12)	0.0006 (9)	−0.0130 (9)	−0.0077 (9)
C12	0.0285 (11)	0.0338 (13)	0.0294 (11)	−0.0005 (9)	−0.0108 (9)	−0.0118 (10)
C13	0.0295 (11)	0.0211 (11)	0.0305 (11)	0.0025 (9)	−0.0107 (9)	−0.0074 (9)
C14	0.0284 (11)	0.0176 (11)	0.0270 (11)	0.0006 (9)	−0.0122 (9)	−0.0064 (9)
C15	0.0257 (11)	0.0175 (10)	0.0236 (10)	0.0007 (8)	−0.0108 (9)	−0.0055 (8)
C16	0.0284 (11)	0.0180 (10)	0.0237 (10)	0.0017 (8)	−0.0131 (9)	−0.0064 (8)
C17	0.0314 (12)	0.0255 (12)	0.0273 (11)	0.0054 (9)	−0.0125 (9)	−0.0119 (9)
C18	0.0292 (12)	0.0452 (15)	0.0402 (13)	0.0077 (11)	−0.0044 (10)	−0.0234 (12)
C19	0.0383 (14)	0.0593 (18)	0.0593 (17)	0.0192 (13)	−0.0192 (13)	−0.0320 (15)
C20	0.0247 (10)	0.0210 (11)	0.0285 (11)	0.0015 (8)	−0.0103 (9)	−0.0096 (9)
C21	0.0246 (10)	0.0169 (10)	0.0267 (11)	0.0009 (8)	−0.0110 (9)	−0.0065 (8)
C22	0.0276 (11)	0.0186 (10)	0.0225 (10)	−0.0001 (9)	−0.0148 (9)	−0.0027 (8)
C23	0.0323 (11)	0.0185 (11)	0.0330 (11)	−0.0043 (9)	−0.0175 (10)	−0.0054 (9)
C24	0.0380 (12)	0.0220 (12)	0.0354 (12)	−0.0013 (10)	−0.0192 (10)	−0.0033 (10)
C25	0.0477 (14)	0.0295 (13)	0.0372 (13)	−0.0068 (11)	−0.0231 (11)	−0.0075 (10)
C26	0.0305 (12)	0.0313 (13)	0.0441 (13)	−0.0056 (10)	−0.0174 (10)	−0.0073 (11)

O1—C6	1.327 (3)	C7—H7B	0.9700
O1—C7	1.447 (3)	C8—H8D	0.9600
O2—C6	1.202 (3)	C8—H8E	0.9600
O3—C9	1.341 (2)	C8—H8F	0.9600
O3—C10	1.473 (2)	C10—C11	1.507 (3)
O4—C9	1.216 (2)	C10—C13	1.508 (3)
O5—C17	1.328 (2)	C10—C12	1.509 (3)
O5—C18	1.442 (3)	C11—H11A	0.9600
O6—C17	1.198 (3)	C11—H11B	0.9600
O7—C22	1.341 (2)	C11—H11C	0.9600
O7—C23	1.471 (2)	C12—H12A	0.9600
O8—C22	1.216 (2)	C12—H12B	0.9600
N1—C1	1.365 (3)	C12—H12C	0.9600
N1—C6	1.379 (3)	C13—H13A	0.9600
N1—N2	1.390 (2)	C13—H13B	0.9600
N2—C2	1.330 (3)	C13—H13C	0.9600
N3—C9	1.336 (3)	C14—C15	1.430 (3)
N3—C5	1.471 (3)	C15—C16	1.329 (3)
N3—C4	1.472 (2)	C15—C21	1.486 (3)
N4—C2	1.347 (3)	C16—C20	1.484 (3)
N4—H4"	0.8999	C18—C19	1.486 (4)
N4—H4'	0.8999	C18—H18A	0.9700
N5—C16	1.365 (3)	C18—H18B	0.9700
N5—C17	1.373 (3)	C19—H19A	0.9600
N5—N6	1.393 (2)	C19—H19B	0.9600
N6—C14	1.330 (3)	C19—H19C	0.9600
N7—C22	1.339 (3)	C20—H20A	0.9700
N7—C21	1.473 (2)	C20—H20B	0.9700
N7—C20	1.477 (3)	C21—H21A	0.9700
N8—C14	1.338 (3)	C21—H21B	0.9700
N8—H8'	0.8600	C23—C24	1.504 (3)
N8—H8"	0.8600	C23—C26	1.511 (3)
C1—C3	1.329 (3)	C23—C25	1.512 (3)
C1—C5	1.482 (3)	C24—H24A	0.9600
C2—C3	1.429 (3)	C24—H24B	0.9600
C3—C4	1.487 (3)	C24—H24C	0.9600
C4—H4D	0.9700	C25—H25A	0.9600
C4—H4E	0.9700	C25—H25B	0.9600
C5—H5A	0.9700	C25—H25C	0.9600
C5—H5B	0.9700	C26—H26A	0.9600
C7—C8	1.494 (4)	C26—H26B	0.9600
C7—H7A	0.9700	C26—H26C	0.9600
C6—O1—C7	116.59 (18)	C10—C12—H12A	109.5
C9—O3—C10	120.85 (15)	C10—C12—H12B	109.5
C17—O5—C18	117.13 (18)	H12A—C12—H12B	109.5
C22—O7—C23	121.69 (16)	C10—C12—H12C	109.5
C1—N1—C6	128.99 (18)	H12A—C12—H12C	109.5
C1—N1—N2	110.17 (16)	H12B—C12—H12C	109.5
C6—N1—N2	120.78 (17)	C10—C13—H13A	109.5
C2—N2—N1	104.91 (16)	C10—C13—H13B	109.5
C9—N3—C5	124.64 (17)	H13A—C13—H13B	109.5
C9—N3—C4	120.16 (17)	C10—C13—H13C	109.5
C5—N3—C4	114.81 (15)	H13A—C13—H13C	109.5
C2—N4—H4"	121.4	H13B—C13—H13C	109.5
C2—N4—H4'	119.3	N6—C14—N8	122.08 (18)
H4"—N4—H4'	112.9	N6—C14—C15	110.37 (17)
C16—N5—C17	128.92 (17)	N8—C14—C15	127.55 (19)
C16—N5—N6	110.18 (16)	C16—C15—C14	106.07 (18)
C17—N5—N6	120.77 (16)	C16—C15—C21	111.02 (17)
C14—N6—N5	104.90 (16)	C14—C15—C21	142.89 (19)
C22—N7—C21	121.67 (17)	C15—C16—N5	108.47 (17)
C22—N7—C20	123.51 (16)	C15—C16—C20	114.67 (18)
C21—N7—C20	114.55 (15)	N5—C16—C20	136.80 (18)
C14—N8—H8'	120.0	O6—C17—O5	126.8 (2)
C14—N8—H8"	120.0	O6—C17—N5	124.59 (19)
H8'—N8—H8"	120.0	O5—C17—N5	108.57 (17)
C3—C1—N1	108.48 (18)	O5—C18—C19	110.85 (19)
C3—C1—C5	114.49 (19)	O5—C18—H18A	109.5
N1—C1—C5	136.95 (19)	C19—C18—H18A	109.5
N2—C2—N4	121.98 (19)	O5—C18—H18B	109.5
N2—C2—C3	110.42 (18)	C19—C18—H18B	109.5
N4—C2—C3	127.6 (2)	H18A—C18—H18B	108.1
C1—C3—C2	106.00 (19)	C18—C19—H19A	109.5
C1—C3—C4	111.15 (17)	C18—C19—H19B	109.5
C2—C3—C4	142.74 (19)	H19A—C19—H19B	109.5
N3—C4—C3	100.28 (16)	C18—C19—H19C	109.5
N3—C4—H4D	111.7	H19A—C19—H19C	109.5
C3—C4—H4D	111.7	H19B—C19—H19C	109.5
N3—C4—H4E	111.7	N7—C20—C16	98.60 (15)
C3—C4—H4E	111.7	N7—C20—H20A	112.0
H4D—C4—H4E	109.5	C16—C20—H20A	112.0
N3—C5—C1	98.69 (16)	N7—C20—H20B	112.0
N3—C5—H5A	112.0	C16—C20—H20B	112.0
C1—C5—H5A	112.0	H20A—C20—H20B	109.7
N3—C5—H5B	112.0	N7—C21—C15	100.59 (16)
C1—C5—H5B	112.0	N7—C21—H21A	111.7
H5A—C5—H5B	109.7	C15—C21—H21A	111.7
O2—C6—O1	127.0 (2)	N7—C21—H21B	111.7
O2—C6—N1	123.8 (2)	C15—C21—H21B	111.7
O1—C6—N1	109.18 (18)	H21A—C21—H21B	109.4
O1—C7—C8	111.1 (2)	O8—C22—N7	124.23 (18)
O1—C7—H7A	109.4	O8—C22—O7	126.38 (18)
C8—C7—H7A	109.4	N7—C22—O7	109.38 (18)
O1—C7—H7B	109.4	O7—C23—C24	110.13 (16)
C8—C7—H7B	109.4	O7—C23—C26	101.64 (17)
H7A—C7—H7B	108.0	C24—C23—C26	109.97 (18)
C7—C8—H8D	109.5	O7—C23—C25	109.88 (16)
C7—C8—H8E	109.5	C24—C23—C25	112.93 (19)
H8D—C8—H8E	109.5	C26—C23—C25	111.72 (18)
C7—C8—H8F	109.5	C23—C24—H24A	109.5
H8D—C8—H8F	109.5	C23—C24—H24B	109.5
H8E—C8—H8F	109.5	H24A—C24—H24B	109.5
O4—C9—N3	123.50 (18)	C23—C24—H24C	109.5
O4—C9—O3	126.06 (18)	H24A—C24—H24C	109.5
N3—C9—O3	110.43 (18)	H24B—C24—H24C	109.5
O3—C10—C11	102.22 (16)	C23—C25—H25A	109.5
O3—C10—C13	108.64 (16)	C23—C25—H25B	109.5
C11—C10—C13	111.19 (16)	H25A—C25—H25B	109.5
O3—C10—C12	111.02 (15)	C23—C25—H25C	109.5
C11—C10—C12	110.14 (18)	H25A—C25—H25C	109.5
C13—C10—C12	113.09 (18)	H25B—C25—H25C	109.5
C10—C11—H11A	109.5	C23—C26—H26A	109.5
C10—C11—H11B	109.5	C23—C26—H26B	109.5
H11A—C11—H11B	109.5	H26A—C26—H26B	109.5
C10—C11—H11C	109.5	C23—C26—H26C	109.5
H11A—C11—H11C	109.5	H26A—C26—H26C	109.5
H11B—C11—H11C	109.5	H26B—C26—H26C	109.5
C1—N1—N2—C2	−0.5 (2)	C9—O3—C10—C13	−67.0 (2)
C6—N1—N2—C2	−178.02 (18)	C9—O3—C10—C12	58.0 (2)
C16—N5—N6—C14	−0.5 (2)	N5—N6—C14—N8	−179.34 (19)
C17—N5—N6—C14	−176.67 (18)	N5—N6—C14—C15	0.6 (2)
C6—N1—C1—C3	177.6 (2)	N6—C14—C15—C16	−0.5 (2)
N2—N1—C1—C3	0.4 (2)	N8—C14—C15—C16	179.4 (2)
C6—N1—C1—C5	−5.9 (4)	N6—C14—C15—C21	−179.0 (3)
N2—N1—C1—C5	176.8 (2)	N8—C14—C15—C21	0.9 (4)
N1—N2—C2—N4	178.65 (18)	C14—C15—C16—N5	0.2 (2)
N1—N2—C2—C3	0.4 (2)	C21—C15—C16—N5	179.20 (16)
N1—C1—C3—C2	−0.1 (2)	C14—C15—C16—C20	−177.62 (17)
C5—C1—C3—C2	−177.45 (17)	C21—C15—C16—C20	1.4 (3)
N1—C1—C3—C4	177.00 (17)	C17—N5—C16—C15	175.96 (19)
C5—C1—C3—C4	−0.4 (3)	N6—N5—C16—C15	0.2 (2)
N2—C2—C3—C1	−0.2 (2)	C17—N5—C16—C20	−7.0 (4)
N4—C2—C3—C1	−178.3 (2)	N6—N5—C16—C20	177.3 (2)
N2—C2—C3—C4	−175.7 (3)	C18—O5—C17—O6	0.6 (3)
N4—C2—C3—C4	6.1 (4)	C18—O5—C17—N5	−179.03 (17)
C9—N3—C4—C3	−165.54 (18)	C16—N5—C17—O6	−180.0 (2)
C5—N3—C4—C3	7.5 (2)	N6—N5—C17—O6	−4.6 (3)
C1—C3—C4—N3	−4.2 (2)	C16—N5—C17—O5	−0.4 (3)
C2—C3—C4—N3	171.2 (3)	N6—N5—C17—O5	175.03 (16)
C9—N3—C5—C1	165.14 (19)	C17—O5—C18—C19	86.1 (3)
C4—N3—C5—C1	−7.6 (2)	C22—N7—C20—C16	−166.46 (18)
C3—C1—C5—N3	4.7 (2)	C21—N7—C20—C16	7.7 (2)
N1—C1—C5—N3	−171.7 (2)	C15—C16—C20—N7	−5.4 (2)
C7—O1—C6—O2	4.9 (3)	N5—C16—C20—N7	177.7 (2)
C7—O1—C6—N1	−174.19 (18)	C22—N7—C21—C15	167.14 (18)
C1—N1—C6—O2	−178.0 (2)	C20—N7—C21—C15	−7.1 (2)
N2—N1—C6—O2	−0.9 (3)	C16—C15—C21—N7	3.3 (2)
C1—N1—C6—O1	1.1 (3)	C14—C15—C21—N7	−178.2 (3)
N2—N1—C6—O1	178.17 (16)	C21—N7—C22—O8	−0.6 (3)
C6—O1—C7—C8	−86.4 (2)	C20—N7—C22—O8	173.13 (19)
C5—N3—C9—O4	179.44 (19)	C21—N7—C22—O7	−179.94 (16)
C4—N3—C9—O4	−8.2 (3)	C20—N7—C22—O7	−6.2 (3)
C5—N3—C9—O3	−2.0 (3)	C23—O7—C22—O8	12.3 (3)
C4—N3—C9—O3	170.39 (16)	C23—O7—C22—N7	−168.41 (16)
C10—O3—C9—O4	−3.2 (3)	C22—O7—C23—C24	55.5 (2)
C10—O3—C9—N3	178.21 (16)	C22—O7—C23—C26	172.01 (17)
C9—O3—C10—C11	175.42 (17)	C22—O7—C23—C25	−69.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8"···O4i	0.86	2.25	3.069 (3)	160
N8—H8'···N2ii	0.86	2.26	3.087 (3)	163
N4—H4'···N6iii	0.90	2.25	3.104 (3)	157
N4—H4"···O8iv	0.90	2.36	3.233 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8"⋯O4i	0.86	2.25	3.069 (3)	160
N8—H8′⋯N2ii	0.86	2.26	3.087 (3)	163
N4—H4′⋯N6iii	0.90	2.25	3.104 (3)	157
N4—H4"⋯O8iv	0.90	2.36	3.233 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .