A second monoclinic polymorph of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-hy-droxy-imino-N'-[1-(pyridin-2-yl)ethyl-idene]acetohydrazide.

The title compound, C14H16N6O2, is a second monoclinic polymorph of 2-[1-(3,5-dimeth-yl)pyrazol-yl]-2-hy-droxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene] acetohydrazide, with two crystallographically independent mol-ecules per asymmetric unit. The non-planar mol-ecules are chemically equal having similar geometric parameters. The previously reported polymorph [Plutenko et al. (2012 ▶). Acta Cryst. E68, o3281] was described in space group Cc (Z = 4). The oxime group and the O atom of the amide group are anti with respect to the C-C bond. In the crystal, mol-ecules are connected by N-H⋯N hydrogen bonds into zigzag chains extending along the b axis.

Related literature

For uses of oxime ligands, see: Penkova et al. (2009 ▶); Kanderal et al. (2005 ▶). For uses of oximes having additional donor functions as versatile ligands, see: Fritsky et al. (1998 ▶, 2004 ▶, 2006 ▶), Kanderal et al. (2005 ▶), Onindo et al. (1995 ▶); Sliva et al. (1997 ▶). For related structures, see: Duda et al. (1997 ▶); Kanderal et al. (2005 ▶); Krämer & Fritsky (2000 ▶); Moroz et al. (2010 ▶, 2012 ▶); Sliva et al. (1997 ▶); Świątek-Kozłowska et al. (2000 ▶); Mokhir et al. (2002 ▶); Penkova et al. (2010 ▶); Strotmeyer et al. (2003 ▶); Fritsky et al. (2000 ▶). For structure of the first polymorph, see Plutenko et al. (2012 ▶). For the synthesis, see: Kozikowski & Adamczyk (1983 ▶).

Experimental

Crystal data

C14H16N6O2

M = 300.33

Monoclinic,

a = 19.4734 (4) Å

b = 7.7679 (2) Å

c = 19.8042 (4) Å

β = 97.552 (1)°

V = 2969.74 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.39 × 0.33 × 0.28 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.964, T max = 0.974

64574 measured reflections

9973 independent reflections

8213 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.03

9973 reflections

419 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009628/fk2070sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009628/fk2070Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009628/fk2070Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009628/fk2070Isup4.cml

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

C14H16N6O2	F(000) = 1264
Mr = 300.33	Dx = 1.343 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9866 reflections
a = 19.4734 (4) Å	θ = 2.8–31.6°
b = 7.7679 (2) Å	µ = 0.10 mm−1
c = 19.8042 (4) Å	T = 100 K
β = 97.552 (1)°	Block, colourless
V = 2969.74 (11) Å3	0.39 × 0.33 × 0.28 mm
Z = 8

Bruker Kappa APEXII DUO CCD diffractometer	9973 independent reflections
Radiation source: fine-focus sealed tube	8213 reflections with I > 2σ(I)
Curved graphite crystal monochromator	Rint = 0.027
Detector resolution: 16 pixels mm-1	θmax = 31.7°, θmin = 1.6°
φ scans and ω scans with κ offset	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −11→11
Tmin = 0.964, Tmax = 0.974	l = −29→29
64574 measured reflections

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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.8835P] where P = (Fo2 + 2Fc2)/3
9973 reflections	(Δ/σ)max = 0.001
419 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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

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 > 2sigma(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	0.23337 (4)	0.28795 (10)	0.54568 (4)	0.02361 (15)
O2	0.24501 (3)	0.03509 (9)	0.75693 (3)	0.01915 (13)
H2O	0.2117 (9)	−0.025 (2)	0.7803 (8)	0.046 (4)*
O3	0.45992 (4)	0.18904 (10)	0.25984 (4)	0.02138 (14)
O4	0.24039 (3)	−0.02793 (9)	0.25464 (3)	0.01929 (13)
H4O	0.2170 (9)	−0.087 (2)	0.2888 (9)	0.052 (5)*
N1	0.09028 (4)	0.25022 (10)	0.52885 (4)	0.01688 (14)
H2N	0.1179 (7)	0.1554 (19)	0.6202 (7)	0.030 (4)*
N2	0.13341 (4)	0.20263 (11)	0.58605 (4)	0.01772 (15)
N3	0.20653 (4)	0.08553 (10)	0.69785 (4)	0.01612 (14)
N4	0.31385 (4)	0.18287 (9)	0.66691 (4)	0.01408 (13)
N5	0.34090 (4)	0.34130 (10)	0.68560 (4)	0.01503 (14)
N6	0.47175 (4)	0.22400 (11)	0.40050 (4)	0.01828 (15)
H7N	0.3769 (8)	0.131 (2)	0.3781 (7)	0.033 (4)*
N7	0.41368 (4)	0.16597 (11)	0.36033 (4)	0.01910 (15)
N8	0.30122 (4)	0.02189 (10)	0.29165 (4)	0.01648 (14)
N9	0.33140 (4)	0.11492 (9)	0.18502 (4)	0.01428 (13)
N10	0.31523 (4)	0.27505 (9)	0.15885 (4)	0.01431 (13)
N11	−0.08655 (4)	0.22180 (11)	0.46263 (4)	0.01968 (15)
N16	0.53482 (4)	0.25441 (12)	0.57576 (4)	0.02314 (17)
C1	0.00368 (5)	0.38205 (12)	0.41941 (4)	0.01765 (16)
H1	0.0500	0.4235	0.4260	0.021*
C2	−0.04025 (5)	0.42371 (13)	0.36098 (5)	0.02003 (17)
H2	−0.0242	0.4911	0.3262	0.024*
C3	−0.10829 (5)	0.36503 (14)	0.35412 (5)	0.02119 (18)
H3	−0.1399	0.3915	0.3147	0.025*
C4	−0.12863 (5)	0.26698 (14)	0.40633 (5)	0.02197 (18)
H4	−0.1754	0.2292	0.4020	0.026*
C5	−0.02103 (4)	0.27821 (12)	0.46846 (4)	0.01566 (15)
C6	0.02508 (4)	0.22338 (12)	0.53059 (4)	0.01642 (16)
C7	−0.00595 (5)	0.14381 (14)	0.58873 (5)	0.02139 (18)
H7A	0.0014	0.2204	0.6284	0.032*
H7B	0.0163	0.0326	0.6004	0.032*
H7C	−0.0557	0.1266	0.5754	0.032*
C8	0.20300 (4)	0.22472 (11)	0.58951 (4)	0.01588 (15)
C9	0.24134 (4)	0.16000 (11)	0.65548 (4)	0.01431 (15)
C10	0.40910 (4)	0.31716 (12)	0.69744 (4)	0.01572 (15)
C11	0.45625 (5)	0.46298 (13)	0.72087 (5)	0.02263 (18)
H11A	0.4290	0.5586	0.7357	0.034*
H11B	0.4807	0.5012	0.6833	0.034*
H11C	0.4900	0.4249	0.7590	0.034*
C12	0.42576 (4)	0.14436 (12)	0.68606 (4)	0.01676 (16)
H12	0.4708	0.0952	0.6904	0.020*
C13	0.36410 (5)	0.06078 (11)	0.66743 (4)	0.01532 (15)
C14	0.34846 (6)	−0.12230 (12)	0.64969 (5)	0.02392 (19)
H14A	0.3254	−0.1296	0.6027	0.036*
H14B	0.3180	−0.1697	0.6807	0.036*
H14C	0.3917	−0.1884	0.6540	0.036*
C15	0.58299 (5)	0.37652 (12)	0.48087 (5)	0.01906 (17)
H15	0.5786	0.3991	0.4334	0.023*
C16	0.64057 (5)	0.43270 (14)	0.52371 (5)	0.02242 (18)
H16	0.6768	0.4924	0.5059	0.027*
C17	0.64462 (5)	0.40039 (15)	0.59324 (5)	0.0246 (2)
H17	0.6834	0.4378	0.6239	0.030*
C18	0.59051 (5)	0.31215 (15)	0.61631 (5)	0.0256 (2)
H18	0.5930	0.2913	0.6638	0.031*
C19	0.53144 (5)	0.28602 (12)	0.50876 (5)	0.01802 (16)
C20	0.46937 (5)	0.21770 (12)	0.46535 (5)	0.01815 (16)
C21	0.41019 (5)	0.14593 (15)	0.49801 (5)	0.02440 (19)
H21A	0.3683	0.2132	0.4836	0.037*
H21B	0.4213	0.1520	0.5477	0.037*
H21C	0.4023	0.0257	0.4841	0.037*
C22	0.41232 (5)	0.15523 (11)	0.29161 (4)	0.01576 (15)
C23	0.34393 (4)	0.09303 (11)	0.25621 (4)	0.01461 (15)
C24	0.30610 (4)	0.25375 (12)	0.09149 (4)	0.01495 (15)
C25	0.28426 (5)	0.40217 (13)	0.04578 (5)	0.02124 (18)
H25A	0.2684	0.4966	0.0727	0.032*
H25B	0.2464	0.3662	0.0111	0.032*
H25C	0.3236	0.4411	0.0236	0.032*
C26	0.31770 (5)	0.08076 (12)	0.07453 (4)	0.01728 (16)
H26	0.3155	0.0333	0.0301	0.021*
C27	0.33293 (5)	−0.00536 (11)	0.13529 (4)	0.01654 (16)
C28	0.34777 (6)	−0.18986 (13)	0.15142 (6)	0.0263 (2)
H28A	0.3918	−0.1995	0.1815	0.039*
H28B	0.3509	−0.2533	0.1092	0.039*
H28C	0.3104	−0.2383	0.1742	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0180 (3)	0.0324 (4)	0.0200 (3)	−0.0017 (3)	0.0009 (2)	0.0084 (3)
O2	0.0143 (3)	0.0255 (3)	0.0163 (3)	−0.0025 (2)	−0.0030 (2)	0.0069 (2)
O3	0.0169 (3)	0.0272 (3)	0.0204 (3)	−0.0039 (3)	0.0040 (2)	−0.0007 (3)
O4	0.0160 (3)	0.0253 (3)	0.0161 (3)	−0.0069 (2)	0.0004 (2)	0.0022 (2)
N1	0.0141 (3)	0.0204 (3)	0.0149 (3)	0.0017 (3)	−0.0026 (2)	0.0008 (3)
N2	0.0129 (3)	0.0239 (4)	0.0154 (3)	0.0002 (3)	−0.0019 (3)	0.0040 (3)
N3	0.0140 (3)	0.0177 (3)	0.0155 (3)	−0.0008 (3)	−0.0022 (2)	0.0023 (3)
N4	0.0114 (3)	0.0138 (3)	0.0166 (3)	−0.0002 (2)	0.0003 (2)	0.0001 (3)
N5	0.0129 (3)	0.0145 (3)	0.0173 (3)	−0.0012 (2)	0.0005 (2)	−0.0010 (3)
N6	0.0155 (3)	0.0217 (4)	0.0167 (3)	−0.0014 (3)	−0.0011 (3)	−0.0006 (3)
N7	0.0158 (3)	0.0260 (4)	0.0152 (3)	−0.0046 (3)	0.0007 (3)	−0.0001 (3)
N8	0.0152 (3)	0.0177 (3)	0.0161 (3)	−0.0020 (3)	0.0005 (3)	0.0012 (3)
N9	0.0167 (3)	0.0135 (3)	0.0129 (3)	−0.0001 (2)	0.0025 (2)	0.0001 (2)
N10	0.0146 (3)	0.0148 (3)	0.0135 (3)	0.0014 (2)	0.0016 (2)	0.0007 (2)
N11	0.0137 (3)	0.0266 (4)	0.0181 (3)	−0.0003 (3)	−0.0002 (3)	−0.0005 (3)
N16	0.0203 (4)	0.0316 (4)	0.0172 (3)	0.0015 (3)	0.0009 (3)	−0.0005 (3)
C1	0.0149 (4)	0.0220 (4)	0.0155 (4)	0.0001 (3)	0.0001 (3)	−0.0009 (3)
C2	0.0201 (4)	0.0246 (4)	0.0148 (4)	0.0016 (3)	0.0001 (3)	−0.0002 (3)
C3	0.0176 (4)	0.0294 (5)	0.0152 (4)	0.0043 (3)	−0.0031 (3)	−0.0027 (3)
C4	0.0132 (4)	0.0321 (5)	0.0195 (4)	0.0000 (3)	−0.0020 (3)	−0.0028 (4)
C5	0.0132 (4)	0.0186 (4)	0.0146 (3)	0.0022 (3)	−0.0002 (3)	−0.0022 (3)
C6	0.0146 (4)	0.0194 (4)	0.0147 (4)	0.0015 (3)	−0.0001 (3)	−0.0006 (3)
C7	0.0169 (4)	0.0288 (5)	0.0184 (4)	0.0009 (3)	0.0021 (3)	0.0037 (3)
C8	0.0141 (4)	0.0171 (4)	0.0155 (3)	0.0003 (3)	−0.0014 (3)	0.0007 (3)
C9	0.0118 (3)	0.0148 (3)	0.0155 (3)	−0.0005 (3)	−0.0010 (3)	0.0002 (3)
C10	0.0126 (4)	0.0201 (4)	0.0142 (3)	−0.0009 (3)	0.0009 (3)	0.0011 (3)
C11	0.0165 (4)	0.0241 (4)	0.0263 (4)	−0.0054 (3)	−0.0005 (3)	−0.0009 (4)
C12	0.0130 (4)	0.0218 (4)	0.0155 (4)	0.0033 (3)	0.0019 (3)	0.0017 (3)
C13	0.0161 (4)	0.0164 (4)	0.0135 (3)	0.0030 (3)	0.0021 (3)	0.0006 (3)
C14	0.0264 (5)	0.0166 (4)	0.0287 (5)	0.0028 (3)	0.0034 (4)	−0.0036 (3)
C15	0.0176 (4)	0.0210 (4)	0.0185 (4)	0.0024 (3)	0.0019 (3)	−0.0019 (3)
C16	0.0162 (4)	0.0257 (4)	0.0249 (4)	0.0021 (3)	0.0010 (3)	−0.0042 (4)
C17	0.0165 (4)	0.0332 (5)	0.0229 (4)	0.0050 (4)	−0.0021 (3)	−0.0070 (4)
C18	0.0216 (4)	0.0367 (5)	0.0175 (4)	0.0052 (4)	−0.0005 (3)	−0.0023 (4)
C19	0.0167 (4)	0.0204 (4)	0.0164 (4)	0.0030 (3)	0.0004 (3)	−0.0018 (3)
C20	0.0165 (4)	0.0205 (4)	0.0172 (4)	0.0007 (3)	0.0015 (3)	−0.0002 (3)
C21	0.0223 (4)	0.0314 (5)	0.0197 (4)	−0.0058 (4)	0.0034 (3)	0.0005 (4)
C22	0.0156 (4)	0.0151 (4)	0.0161 (4)	0.0001 (3)	0.0004 (3)	0.0005 (3)
C23	0.0154 (4)	0.0145 (3)	0.0138 (3)	0.0001 (3)	0.0012 (3)	0.0008 (3)
C24	0.0116 (3)	0.0198 (4)	0.0134 (3)	0.0001 (3)	0.0015 (3)	−0.0001 (3)
C25	0.0212 (4)	0.0259 (4)	0.0162 (4)	0.0049 (3)	0.0012 (3)	0.0030 (3)
C26	0.0159 (4)	0.0212 (4)	0.0149 (4)	−0.0013 (3)	0.0027 (3)	−0.0037 (3)
C27	0.0158 (4)	0.0162 (4)	0.0183 (4)	−0.0019 (3)	0.0048 (3)	−0.0031 (3)
C28	0.0349 (5)	0.0151 (4)	0.0311 (5)	−0.0007 (4)	0.0126 (4)	−0.0015 (4)

O1—C8	1.2162 (11)	C7—H7B	0.9800
O2—N3	1.3615 (9)	C7—H7C	0.9800
O2—H2O	0.964 (17)	C8—C9	1.5035 (12)
O3—C22	1.2156 (11)	C10—C12	1.4061 (13)
O4—N8	1.3645 (10)	C10—C11	1.4931 (13)
O4—H4O	0.978 (18)	C11—H11A	0.9800
N1—C6	1.2915 (11)	C11—H11B	0.9800
N1—N2	1.3693 (10)	C11—H11C	0.9800
N2—C8	1.3589 (11)	C12—C13	1.3721 (12)
N2—H2N	0.859 (15)	C12—H12	0.9500
N3—C9	1.2836 (11)	C13—C14	1.4868 (13)
N4—C13	1.3619 (11)	C14—H14A	0.9800
N4—N5	1.3703 (10)	C14—H14B	0.9800
N4—C9	1.4115 (11)	C14—H14C	0.9800
N5—C10	1.3313 (11)	C15—C16	1.3846 (13)
N6—C20	1.2921 (12)	C15—C19	1.3974 (13)
N6—N7	1.3705 (11)	C15—H15	0.9500
N7—C22	1.3603 (11)	C16—C17	1.3916 (14)
N7—H7N	0.882 (15)	C16—H16	0.9500
N8—C23	1.2819 (11)	C17—C18	1.3840 (15)
N9—C27	1.3607 (11)	C17—H17	0.9500
N9—N10	1.3683 (10)	C18—H18	0.9500
N9—C23	1.4090 (11)	C19—C20	1.4862 (13)
N10—C24	1.3327 (11)	C20—C21	1.5010 (13)
N11—C5	1.3396 (11)	C21—H21A	0.9800
N11—C4	1.3408 (12)	C21—H21B	0.9800
N16—C18	1.3391 (13)	C21—H21C	0.9800
N16—C19	1.3425 (12)	C22—C23	1.5010 (12)
C1—C2	1.3841 (12)	C24—C26	1.4105 (13)
C1—C5	1.3959 (12)	C24—C25	1.4927 (13)
C1—H1	0.9500	C25—H25A	0.9800
C2—C3	1.3909 (14)	C25—H25B	0.9800
C2—H2	0.9500	C25—H25C	0.9800
C3—C4	1.3834 (14)	C26—C27	1.3747 (13)
C3—H3	0.9500	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.4884 (13)
C5—C6	1.4872 (12)	C28—H28A	0.9800
C6—C7	1.5019 (13)	C28—H28B	0.9800
C7—H7A	0.9800	C28—H28C	0.9800
N3—O2—H2O	102.8 (10)	C13—C12—H12	126.8
N8—O4—H4O	102.3 (10)	C10—C12—H12	126.8
C6—N1—N2	115.63 (8)	N4—C13—C12	105.97 (8)
C8—N2—N1	120.46 (8)	N4—C13—C14	122.66 (8)
C8—N2—H2N	117.7 (10)	C12—C13—C14	131.37 (8)
N1—N2—H2N	121.8 (10)	C13—C14—H14A	109.5
C9—N3—O2	114.41 (7)	C13—C14—H14B	109.5
C13—N4—N5	111.90 (7)	H14A—C14—H14B	109.5
C13—N4—C9	128.04 (8)	C13—C14—H14C	109.5
N5—N4—C9	119.83 (7)	H14A—C14—H14C	109.5
C10—N5—N4	105.09 (7)	H14B—C14—H14C	109.5
C20—N6—N7	115.45 (8)	C16—C15—C19	118.83 (9)
C22—N7—N6	120.46 (8)	C16—C15—H15	120.6
C22—N7—H7N	118.1 (10)	C19—C15—H15	120.6
N6—N7—H7N	121.4 (10)	C15—C16—C17	119.05 (9)
C23—N8—O4	114.08 (7)	C15—C16—H16	120.5
C27—N9—N10	112.07 (7)	C17—C16—H16	120.5
C27—N9—C23	128.60 (8)	C18—C17—C16	117.99 (9)
N10—N9—C23	119.32 (7)	C18—C17—H17	121.0
C24—N10—N9	105.08 (7)	C16—C17—H17	121.0
C5—N11—C4	117.20 (8)	N16—C18—C17	124.04 (9)
C18—N16—C19	117.51 (9)	N16—C18—H18	118.0
C2—C1—C5	119.02 (8)	C17—C18—H18	118.0
C2—C1—H1	120.5	N16—C19—C15	122.57 (9)
C5—C1—H1	120.5	N16—C19—C20	115.91 (8)
C1—C2—C3	118.76 (9)	C15—C19—C20	121.53 (8)
C1—C2—H2	120.6	N6—C20—C19	115.39 (8)
C3—C2—H2	120.6	N6—C20—C21	124.91 (8)
C4—C3—C2	118.04 (8)	C19—C20—C21	119.70 (8)
C4—C3—H3	121.0	C20—C21—H21A	109.5
C2—C3—H3	121.0	C20—C21—H21B	109.5
N11—C4—C3	124.19 (9)	H21A—C21—H21B	109.5
N11—C4—H4	117.9	C20—C21—H21C	109.5
C3—C4—H4	117.9	H21A—C21—H21C	109.5
N11—C5—C1	122.73 (8)	H21B—C21—H21C	109.5
N11—C5—C6	116.25 (8)	O3—C22—N7	126.06 (8)
C1—C5—C6	121.02 (8)	O3—C22—C23	121.19 (8)
N1—C6—C5	114.87 (8)	N7—C22—C23	112.74 (7)
N1—C6—C7	125.65 (8)	N8—C23—N9	124.08 (8)
C5—C6—C7	119.48 (8)	N8—C23—C22	118.86 (8)
C6—C7—H7A	109.5	N9—C23—C22	117.06 (7)
C6—C7—H7B	109.5	N10—C24—C26	110.62 (8)
H7A—C7—H7B	109.5	N10—C24—C25	120.07 (8)
C6—C7—H7C	109.5	C26—C24—C25	129.28 (8)
H7A—C7—H7C	109.5	C24—C25—H25A	109.5
H7B—C7—H7C	109.5	C24—C25—H25B	109.5
O1—C8—N2	126.18 (8)	H25A—C25—H25B	109.5
O1—C8—C9	121.51 (8)	C24—C25—H25C	109.5
N2—C8—C9	112.31 (7)	H25A—C25—H25C	109.5
N3—C9—N4	123.70 (8)	H25B—C25—H25C	109.5
N3—C9—C8	118.31 (8)	C27—C26—C24	106.14 (8)
N4—C9—C8	117.99 (7)	C27—C26—H26	126.9
N5—C10—C12	110.61 (8)	C24—C26—H26	126.9
N5—C10—C11	120.42 (8)	N9—C27—C26	106.07 (8)
C12—C10—C11	128.96 (8)	N9—C27—C28	121.87 (8)
C10—C11—H11A	109.5	C26—C27—C28	132.05 (9)
C10—C11—H11B	109.5	C27—C28—H28A	109.5
H11A—C11—H11B	109.5	C27—C28—H28B	109.5
C10—C11—H11C	109.5	H28A—C28—H28B	109.5
H11A—C11—H11C	109.5	C27—C28—H28C	109.5
H11B—C11—H11C	109.5	H28A—C28—H28C	109.5
C13—C12—C10	106.42 (8)	H28B—C28—H28C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N5i	0.964 (17)	1.664 (17)	2.6193 (10)	170.1 (16)
O4—H4O···N10ii	0.978 (18)	1.670 (18)	2.6341 (10)	167.8 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N5i	0.964 (17)	1.664 (17)	2.6193 (10)	170.1 (16)
O4—H4O⋯N10ii	0.978 (18)	1.670 (18)	2.6341 (10)	167.8 (17)

Symmetry codes: (i) ; (ii) .