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The synthesis of the title compound as a formic acid salt, rather than the standard hydro­chloride salt that is commercially available, and its spectroscopic and crystallographic characterization are described.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902300974X/jy2036sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300974X/jy2036Isup2.hkl
Contains datablock I

docx

Microsoft Word (DOCX) file https://doi.org/10.1107/S205698902300974X/jy2036sup3.docx
The SI contains NMR and IR spectroscopy data of the titled compound.

mol

MDL mol file https://doi.org/10.1107/S205698902300974X/jy2036sup4.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698902300974X/jy2036Isup5.cml
Supplementary material

CCDC reference: 2306392

Computing details top

6-Hydroxy-1,2-dihydropyridin-2-one top
Crystal data top
C30H30N6O12F(000) = 1392
Mr = 666.60Dx = 1.444 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 9.58785 (4) ÅCell parameters from 59431 reflections
b = 16.83642 (8) Åθ = 3.5–78.0°
c = 19.55978 (10) ŵ = 0.97 mm1
β = 103.7319 (5)°T = 100 K
V = 3067.19 (3) Å3Block, clear colourless
Z = 40.38 × 0.12 × 0.10 mm
Data collection top
XtaLAB Synergy, Dualflex, HyPix
diffractometer
6554 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source6155 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.0000 pixels mm-1θmax = 78.1°, θmin = 3.5°
ω scansh = 1112
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2021)
k = 2121
Tmin = 0.453, Tmax = 1.000l = 2424
83138 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0411P)2 + 1.0736P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6554 reflectionsΔρmax = 0.19 e Å3
477 parametersΔρmin = 0.35 e Å3
14 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.99326 (7)0.14764 (4)0.52810 (4)0.02046 (15)
O20.52056 (7)0.20046 (5)0.45281 (4)0.02307 (16)
H2A0.433 (2)0.190 (2)0.449 (2)0.028*0.39 (3)
N10.75397 (8)0.16938 (5)0.49622 (4)0.01657 (16)
H10.7731 (13)0.2085 (7)0.4701 (6)0.020*
C10.86759 (10)0.12574 (6)0.53339 (5)0.01703 (19)
C20.83551 (11)0.06266 (6)0.57353 (5)0.0215 (2)
H2B0.9101240.0310890.6011410.026*
C30.69311 (11)0.04690 (6)0.57242 (6)0.0228 (2)
H3A0.6717490.0041900.5999980.027*
C40.58049 (10)0.09106 (6)0.53259 (5)0.0196 (2)
H4B0.4837730.0785500.5323770.024*
C50.61270 (10)0.15408 (6)0.49300 (5)0.01704 (19)
O30.26881 (7)0.17595 (5)0.44883 (4)0.02250 (16)
H30.3589 (19)0.1824 (14)0.4497 (13)0.027*0.61 (3)
O40.19312 (7)0.12596 (5)0.35615 (4)0.02344 (16)
H40.2704 (15)0.1017 (8)0.3202 (7)0.028*
N20.04226 (8)0.14771 (5)0.39488 (4)0.01710 (16)
H20.0221 (13)0.1564 (8)0.4363 (6)0.021*
C60.18169 (10)0.15386 (6)0.39087 (5)0.01790 (19)
C70.21482 (11)0.13432 (6)0.32713 (6)0.0213 (2)
H70.3106690.1376360.3219140.026*
C80.10467 (11)0.11005 (7)0.27185 (6)0.0239 (2)
H80.1268990.0952900.2287710.029*
C90.03761 (11)0.10639 (6)0.27684 (5)0.0219 (2)
H90.1118930.0909070.2376950.026*
C100.06756 (10)0.12600 (6)0.34062 (5)0.01782 (19)
O51.10984 (8)0.44209 (4)0.77157 (4)0.02427 (17)
O60.69473 (7)0.46139 (4)0.60703 (4)0.02291 (16)
H60.633 (3)0.4403 (16)0.5726 (11)0.027*0.51 (3)
N30.90320 (8)0.44362 (5)0.68705 (4)0.01738 (17)
H3B0.8924 (13)0.4921 (7)0.7009 (7)0.021*
C111.02185 (10)0.40333 (6)0.72324 (5)0.01834 (19)
C121.03646 (12)0.32439 (6)0.70413 (6)0.0254 (2)
H121.1161690.2934980.7279410.030*
C130.93248 (13)0.29207 (7)0.64981 (6)0.0295 (2)
H130.9425210.2383760.6368330.035*
C140.81402 (11)0.33486 (6)0.61347 (6)0.0240 (2)
H140.7449930.3112120.5760360.029*
C150.79897 (10)0.41320 (6)0.63325 (5)0.01727 (19)
O70.51409 (7)0.40623 (4)0.50930 (4)0.02113 (15)
H7A0.579 (3)0.4265 (17)0.5446 (12)0.025*0.49 (3)
O80.06505 (7)0.32983 (5)0.41128 (4)0.02330 (16)
H8A0.0264 (13)0.3226 (8)0.4150 (7)0.028*
N40.28349 (8)0.37226 (5)0.46665 (4)0.01696 (17)
H4A0.3118 (13)0.3515 (8)0.4316 (6)0.020*
C160.38461 (10)0.41017 (6)0.51679 (5)0.01732 (19)
C170.33735 (11)0.44811 (6)0.57103 (5)0.0218 (2)
H170.4029670.4761820.6069260.026*
C180.19353 (12)0.44388 (7)0.57127 (6)0.0260 (2)
H180.1616760.4692690.6081960.031*
C190.09332 (11)0.40380 (7)0.51941 (6)0.0239 (2)
H190.0048150.4010250.5210120.029*
C200.14144 (10)0.36826 (6)0.46563 (5)0.01835 (19)
O90.18597 (7)0.69692 (4)0.58239 (4)0.02126 (15)
O100.66116 (7)0.66705 (4)0.66883 (4)0.01849 (15)
H100.7367 (13)0.6395 (8)0.6998 (7)0.022*
N50.42153 (8)0.67871 (5)0.63253 (4)0.01655 (16)
H50.4396 (13)0.7114 (7)0.6004 (6)0.020*
C210.28056 (10)0.66605 (6)0.63264 (5)0.01715 (19)
C220.25389 (10)0.61994 (6)0.68815 (5)0.0203 (2)
H220.1582200.6101050.6915820.024*
C230.36839 (11)0.58916 (6)0.73752 (6)0.0224 (2)
H230.3497500.5582530.7750090.027*
C240.51056 (11)0.60179 (6)0.73441 (5)0.0203 (2)
H240.5879060.5792910.7684590.024*
C250.53506 (10)0.64807 (6)0.68018 (5)0.01634 (18)
O110.64103 (7)0.09175 (4)0.75468 (4)0.01983 (15)
O120.20548 (7)0.07976 (5)0.60556 (4)0.02324 (16)
H12A0.1306 (14)0.1044 (8)0.5774 (7)0.028*
N60.42400 (8)0.09381 (5)0.67740 (4)0.01662 (16)
H6A0.4165 (13)0.0440 (7)0.6899 (7)0.020*
C260.54837 (10)0.13190 (6)0.70929 (5)0.01743 (19)
C270.56380 (12)0.21052 (6)0.68974 (6)0.0260 (2)
H270.6497100.2389770.7089970.031*
C280.45219 (13)0.24630 (7)0.64195 (6)0.0304 (3)
H280.4624240.3001020.6293250.036*
C290.32527 (12)0.20661 (7)0.61155 (6)0.0249 (2)
H290.2491730.2327170.5794420.030*
C300.31366 (10)0.12804 (6)0.62962 (5)0.01851 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0114 (3)0.0298 (4)0.0185 (3)0.0016 (3)0.0002 (2)0.0008 (3)
O20.0104 (3)0.0268 (4)0.0301 (4)0.0005 (3)0.0013 (3)0.0117 (3)
N10.0118 (4)0.0194 (4)0.0174 (4)0.0001 (3)0.0013 (3)0.0032 (3)
C10.0133 (4)0.0214 (5)0.0148 (4)0.0020 (3)0.0000 (3)0.0032 (3)
C20.0195 (5)0.0217 (5)0.0210 (5)0.0054 (4)0.0002 (4)0.0031 (4)
C30.0237 (5)0.0199 (5)0.0244 (5)0.0007 (4)0.0050 (4)0.0050 (4)
C40.0157 (4)0.0202 (5)0.0229 (5)0.0015 (3)0.0041 (4)0.0014 (4)
C50.0127 (4)0.0191 (4)0.0181 (4)0.0002 (3)0.0013 (3)0.0003 (4)
O30.0113 (3)0.0326 (4)0.0218 (4)0.0029 (3)0.0005 (3)0.0013 (3)
O40.0125 (3)0.0331 (4)0.0237 (4)0.0050 (3)0.0022 (3)0.0064 (3)
N20.0123 (4)0.0207 (4)0.0177 (4)0.0014 (3)0.0024 (3)0.0020 (3)
C60.0127 (4)0.0177 (4)0.0222 (5)0.0001 (3)0.0019 (3)0.0020 (4)
C70.0164 (4)0.0239 (5)0.0247 (5)0.0015 (4)0.0069 (4)0.0037 (4)
C80.0255 (5)0.0271 (5)0.0205 (5)0.0003 (4)0.0082 (4)0.0002 (4)
C90.0205 (5)0.0246 (5)0.0187 (5)0.0031 (4)0.0008 (4)0.0023 (4)
C100.0144 (4)0.0167 (4)0.0209 (5)0.0019 (3)0.0011 (4)0.0001 (4)
O50.0181 (3)0.0227 (4)0.0261 (4)0.0047 (3)0.0066 (3)0.0051 (3)
O60.0158 (3)0.0241 (4)0.0241 (4)0.0013 (3)0.0048 (3)0.0018 (3)
N30.0143 (4)0.0166 (4)0.0193 (4)0.0007 (3)0.0001 (3)0.0023 (3)
C110.0146 (4)0.0211 (5)0.0179 (4)0.0013 (3)0.0010 (3)0.0003 (4)
C120.0238 (5)0.0218 (5)0.0274 (5)0.0069 (4)0.0004 (4)0.0019 (4)
C130.0319 (6)0.0213 (5)0.0319 (6)0.0038 (4)0.0007 (5)0.0073 (4)
C140.0225 (5)0.0238 (5)0.0227 (5)0.0027 (4)0.0002 (4)0.0059 (4)
C150.0133 (4)0.0219 (5)0.0158 (4)0.0022 (3)0.0019 (3)0.0006 (4)
O70.0119 (3)0.0277 (4)0.0218 (4)0.0025 (3)0.0001 (3)0.0025 (3)
O80.0117 (3)0.0300 (4)0.0265 (4)0.0043 (3)0.0012 (3)0.0042 (3)
N40.0128 (4)0.0200 (4)0.0176 (4)0.0006 (3)0.0026 (3)0.0009 (3)
C160.0146 (4)0.0174 (4)0.0181 (4)0.0012 (3)0.0001 (3)0.0039 (3)
C170.0226 (5)0.0223 (5)0.0189 (5)0.0026 (4)0.0020 (4)0.0014 (4)
C180.0267 (5)0.0274 (5)0.0261 (5)0.0009 (4)0.0108 (4)0.0036 (4)
C190.0168 (4)0.0271 (5)0.0299 (5)0.0009 (4)0.0093 (4)0.0003 (4)
C200.0134 (4)0.0181 (4)0.0224 (5)0.0010 (3)0.0020 (4)0.0037 (4)
O90.0110 (3)0.0253 (4)0.0252 (4)0.0008 (3)0.0002 (3)0.0068 (3)
O100.0106 (3)0.0242 (3)0.0193 (3)0.0011 (3)0.0008 (2)0.0022 (3)
N50.0120 (4)0.0197 (4)0.0171 (4)0.0001 (3)0.0017 (3)0.0038 (3)
C210.0126 (4)0.0175 (4)0.0204 (5)0.0004 (3)0.0020 (3)0.0008 (4)
C220.0152 (4)0.0232 (5)0.0237 (5)0.0004 (4)0.0070 (4)0.0016 (4)
C230.0236 (5)0.0242 (5)0.0207 (5)0.0012 (4)0.0077 (4)0.0050 (4)
C240.0182 (5)0.0231 (5)0.0180 (5)0.0041 (4)0.0014 (4)0.0036 (4)
C250.0132 (4)0.0179 (4)0.0168 (4)0.0007 (3)0.0013 (3)0.0022 (3)
O110.0143 (3)0.0197 (3)0.0214 (3)0.0014 (3)0.0040 (3)0.0039 (3)
O120.0131 (3)0.0304 (4)0.0222 (4)0.0006 (3)0.0038 (3)0.0036 (3)
N60.0130 (4)0.0185 (4)0.0166 (4)0.0002 (3)0.0000 (3)0.0022 (3)
C260.0146 (4)0.0203 (5)0.0159 (4)0.0001 (3)0.0008 (3)0.0004 (4)
C270.0254 (5)0.0202 (5)0.0264 (5)0.0045 (4)0.0055 (4)0.0018 (4)
C280.0369 (6)0.0184 (5)0.0291 (6)0.0001 (4)0.0058 (5)0.0038 (4)
C290.0249 (5)0.0234 (5)0.0213 (5)0.0067 (4)0.0045 (4)0.0021 (4)
C300.0138 (4)0.0254 (5)0.0151 (4)0.0031 (4)0.0010 (3)0.0012 (4)
Geometric parameters (Å, º) top
O1—C11.2875 (12)O7—H7A0.879 (18)
O2—H2A0.839 (19)O7—C161.2858 (12)
O2—C51.2956 (12)O8—H8A0.905 (12)
N1—H10.880 (12)O8—C201.3098 (12)
N1—C11.3708 (12)N4—H4A0.868 (12)
N1—C51.3655 (12)N4—C161.3630 (12)
C1—C21.3978 (15)N4—C201.3590 (12)
C2—H2B0.9500C16—C171.4026 (15)
C2—C31.3859 (15)C17—H170.9500
C3—H3A0.9500C17—C181.3819 (15)
C3—C41.3879 (14)C18—H180.9500
C4—H4B0.9500C18—C191.3946 (15)
C4—C51.3908 (14)C19—H190.9500
O3—H30.867 (17)C19—C201.3811 (15)
O3—C61.2928 (12)O9—C211.2789 (12)
O4—H40.981 (14)O10—H100.948 (11)
O4—C101.3096 (12)O10—C251.3193 (12)
N2—H20.888 (12)N5—H50.882 (12)
N2—C61.3616 (12)N5—C211.3688 (12)
N2—C101.3556 (12)N5—C251.3557 (12)
C6—C71.3971 (15)C21—C221.4067 (14)
C7—H70.9500C22—H220.9500
C7—C81.3818 (15)C22—C231.3795 (14)
C8—H80.9500C23—H230.9500
C8—C91.3919 (15)C23—C241.3952 (14)
C9—H90.9500C24—H240.9500
C9—C101.3850 (15)C24—C251.3805 (14)
O5—C111.2856 (12)O11—C261.2884 (12)
O6—H60.861 (14)O12—H12A0.897 (12)
O6—C151.2949 (12)O12—C301.3139 (12)
N3—H3B0.874 (12)N6—H6A0.881 (12)
N3—C111.3686 (12)N6—C261.3671 (12)
N3—C151.3672 (12)N6—C301.3622 (12)
C11—C121.3966 (14)C26—C271.3955 (14)
C12—H120.9500C27—H270.9500
C12—C131.3843 (15)C27—C281.3810 (15)
C13—H130.9500C28—H280.9500
C13—C141.3896 (15)C28—C291.3919 (16)
C14—H140.9500C29—H290.9500
C14—C151.3916 (15)C29—C301.3805 (15)
C5—O2—H2A117 (3)C16—O7—H7A114.1 (19)
C1—N1—H1117.4 (8)C20—O8—H8A111.5 (9)
C5—N1—H1117.1 (8)C16—N4—H4A117.0 (8)
C5—N1—C1125.31 (9)C20—N4—H4A118.0 (8)
O1—C1—N1116.42 (9)C20—N4—C16124.96 (9)
O1—C1—C2126.71 (9)O7—C16—N4115.79 (9)
N1—C1—C2116.88 (9)O7—C16—C17127.13 (9)
C1—C2—H2B120.5N4—C16—C17117.07 (9)
C3—C2—C1118.94 (9)C16—C17—H17120.6
C3—C2—H2B120.5C18—C17—C16118.75 (9)
C2—C3—H3A118.7C18—C17—H17120.6
C2—C3—C4122.58 (9)C17—C18—H18118.7
C4—C3—H3A118.7C17—C18—C19122.56 (10)
C3—C4—H4B120.8C19—C18—H18118.7
C3—C4—C5118.37 (9)C18—C19—H19121.1
C5—C4—H4B120.8C20—C19—C18117.81 (9)
O2—C5—N1116.12 (9)C20—C19—H19121.1
O2—C5—C4126.02 (9)O8—C20—N4113.69 (9)
N1—C5—C4117.85 (9)O8—C20—C19127.49 (9)
C6—O3—H3119.1 (16)N4—C20—C19118.83 (9)
C10—O4—H4114.4 (8)C25—O10—H10111.5 (8)
C6—N2—H2118.0 (8)C25—N5—C21124.86 (9)
C10—N2—H2117.5 (8)C21—N5—H5117.3 (8)
C10—N2—C6124.49 (9)C25—N5—H5117.8 (8)
O3—C6—N2114.22 (9)O9—C21—N5117.12 (9)
O3—C6—C7127.87 (9)O9—C21—C22126.28 (9)
N2—C6—C7117.89 (9)N5—C21—C22116.60 (8)
C6—C7—H7120.8C21—C22—H22120.4
C8—C7—C6118.33 (9)C23—C22—C21119.17 (9)
C8—C7—H7120.8C23—C22—H22120.4
C7—C8—H8118.7C22—C23—H23118.8
C7—C8—C9122.55 (10)C22—C23—C24122.38 (9)
C9—C8—H8118.7C24—C23—H23118.8
C8—C9—H9121.0C23—C24—H24121.1
C10—C9—C8117.96 (9)C25—C24—C23117.76 (9)
C10—C9—H9121.0C25—C24—H24121.1
O4—C10—N2113.87 (9)O10—C25—N5114.23 (8)
O4—C10—C9127.39 (9)O10—C25—C24126.58 (9)
N2—C10—C9118.74 (9)N5—C25—C24119.19 (9)
C15—O6—H6112.0 (19)C30—O12—H12A112.5 (9)
C11—N3—H3B116.6 (8)C26—N6—H6A116.1 (8)
C15—N3—H3B118.0 (8)C30—N6—H6A119.5 (8)
C15—N3—C11125.33 (9)C30—N6—C26124.46 (9)
O5—C11—N3116.65 (9)O11—C26—N6116.90 (9)
O5—C11—C12126.15 (9)O11—C26—C27125.87 (9)
N3—C11—C12117.21 (9)N6—C26—C27117.24 (9)
C11—C12—H12120.7C26—C27—H27120.5
C13—C12—C11118.67 (10)C28—C27—C26118.93 (10)
C13—C12—H12120.7C28—C27—H27120.5
C12—C13—H13118.6C27—C28—H28118.7
C12—C13—C14122.76 (10)C27—C28—C29122.56 (10)
C14—C13—H13118.6C29—C28—H28118.7
C13—C14—H14120.8C28—C29—H29121.1
C13—C14—C15118.38 (9)C30—C29—C28117.79 (9)
C15—C14—H14120.8C30—C29—H29121.1
O6—C15—N3115.11 (9)O12—C30—N6113.73 (9)
O6—C15—C14127.23 (9)O12—C30—C29127.30 (9)
N3—C15—C14117.65 (9)N6—C30—C29118.97 (9)
O1—C1—C2—C3179.28 (10)O7—C16—C17—C18178.06 (10)
N1—C1—C2—C31.34 (14)N4—C16—C17—C181.06 (14)
C1—N1—C5—O2177.46 (9)C16—N4—C20—O8178.71 (9)
C1—N1—C5—C42.61 (15)C16—N4—C20—C191.01 (15)
C1—C2—C3—C40.39 (16)C16—C17—C18—C190.44 (17)
C2—C3—C4—C50.75 (16)C17—C18—C19—C200.91 (17)
C3—C4—C5—O2179.42 (10)C18—C19—C20—O8178.08 (10)
C3—C4—C5—N10.66 (14)C18—C19—C20—N41.60 (15)
C5—N1—C1—O1177.61 (9)C20—N4—C16—O7178.86 (9)
C5—N1—C1—C22.95 (14)C20—N4—C16—C170.35 (14)
O3—C6—C7—C8178.33 (10)O9—C21—C22—C23178.40 (10)
N2—C6—C7—C80.10 (14)N5—C21—C22—C231.37 (14)
C6—N2—C10—O4178.47 (9)C21—N5—C25—O10178.72 (9)
C6—N2—C10—C91.86 (15)C21—N5—C25—C241.47 (15)
C6—C7—C8—C91.70 (16)C21—C22—C23—C240.27 (16)
C7—C8—C9—C101.75 (16)C22—C23—C24—C251.14 (16)
C8—C9—C10—O4179.62 (10)C23—C24—C25—O10179.46 (9)
C8—C9—C10—N20.00 (15)C23—C24—C25—N50.31 (15)
C10—N2—C6—O3179.62 (9)C25—N5—C21—O9177.48 (9)
C10—N2—C6—C71.91 (15)C25—N5—C21—C222.31 (14)
O5—C11—C12—C13178.89 (11)O11—C26—C27—C28177.73 (11)
N3—C11—C12—C130.80 (16)N6—C26—C27—C282.43 (16)
C11—N3—C15—O6179.01 (9)C26—N6—C30—O12179.47 (9)
C11—N3—C15—C140.10 (15)C26—N6—C30—C290.36 (15)
C11—C12—C13—C140.03 (19)C26—C27—C28—C291.01 (19)
C12—C13—C14—C150.74 (18)C27—C28—C29—C301.18 (19)
C13—C14—C15—O6178.07 (11)C28—C29—C30—O12177.96 (11)
C13—C14—C15—N30.70 (15)C28—C29—C30—N61.84 (16)
C15—N3—C11—O5178.86 (9)C30—N6—C26—O11178.32 (9)
C15—N3—C11—C120.86 (15)C30—N6—C26—C271.83 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O30.84 (2)1.60 (2)2.4317 (10)174 (4)
N1—H1···O9i0.88 (1)1.98 (1)2.8606 (11)175 (1)
O3—H3···O20.87 (2)1.57 (2)2.4317 (10)176 (3)
O4—H4···O5ii0.981 (14)1.500 (14)2.4768 (10)173.5 (14)
N2—H2···O1iii0.89 (1)1.89 (1)2.7554 (11)166 (1)
O6—H6···O70.86 (1)1.58 (1)2.4381 (10)177 (3)
N3—H3B···O11iv0.87 (1)1.95 (1)2.8155 (11)170 (1)
O7—H7A···O60.88 (2)1.56 (2)2.4381 (10)179 (3)
O8—H8A···O9v0.91 (1)1.58 (1)2.4803 (10)175 (1)
N4—H4A···O10i0.87 (1)2.07 (1)2.8999 (11)161 (1)
O10—H10···O11iv0.95 (1)1.52 (1)2.4690 (9)176 (1)
N5—H5···O2i0.88 (1)1.90 (1)2.7699 (11)167 (1)
O12—H12A···O1iii0.90 (1)1.61 (1)2.5057 (10)178 (2)
N6—H6A···O5vi0.88 (1)1.91 (1)2.7893 (11)172 (1)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x3/2, y+1/2, z1/2; (iii) x1, y, z; (iv) x+3/2, y+1/2, z+3/2; (v) x, y+1, z+1; (vi) x+3/2, y1/2, z+3/2.
Selected bond lengths (Å) and angles (°). top
N(5)-C(21)1.3688 (12)O(10)-C(25)-N(5)114.23 (8)
N(5)-C(25)1.3557 (12)O(10)-C(25)-C(24)126.58 (9)
N(5)-C(25)-C(24)119.19 (9)
O(9)-C(21)1.2789 (12)
O(10)-C(25)1.3193 (12)C(25)-N(5)-C(21)124.86 (9)
C(21)-N(5)-H(5)117.3 (8)
C(25)-N(5)-H(5)117.8 (8)
O(9)-C(21)-N(5)117.12 (9)
N(5)-C(21)-C(22)116.60 (8)
O(9)-C(21)-C(22)126.28 (9)
 

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