Synthesis and crystallographic characterization of 6-hydroxy-1,2-dihydropyridin-2-one

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O11      --C26      .        6.2 s.u.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT977_ALERT_2_C Check Negative Difference Density on H10       .      -0.32 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         26 Note
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00008 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00010 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  1  )      12.39 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )      13.61 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )      12.51 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  4  )      13.49 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         22 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         22 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

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

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Computing details

6-Hydroxy-1,2-dihydropyridin-2-one

Crystal data

C30H30N6O12	F(000) = 1392
Mr = 666.60	Dx = 1.444 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 9.58785 (4) Å	Cell parameters from 59431 reflections
b = 16.83642 (8) Å	θ = 3.5–78.0°
c = 19.55978 (10) Å	µ = 0.97 mm^−1
β = 103.7319 (5)°	T = 100 K
V = 3067.19 (3) Å^3	Block, clear colourless
Z = 4	0.38 × 0.12 × 0.10 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	6554 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	6155 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.0000 pixels mm^-1	θmax = 78.1°, θmin = 3.5°
ω scans	h = −11→12
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021)	k = −21→21
Tmin = 0.453, Tmax = 1.000	l = −24→24
83138 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 1.0736P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6554 reflections	Δρmax = 0.19 e Å^−3
477 parameters	Δρmin = −0.35 e Å^−3
14 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.99326 (7)	0.14764 (4)	0.52810 (4)	0.02046 (15)
O2	0.52056 (7)	0.20046 (5)	0.45281 (4)	0.02307 (16)
H2A	0.433 (2)	0.190 (2)	0.449 (2)	0.028*	0.39 (3)
N1	0.75397 (8)	0.16938 (5)	0.49622 (4)	0.01657 (16)
H1	0.7731 (13)	0.2085 (7)	0.4701 (6)	0.020*
C1	0.86759 (10)	0.12574 (6)	0.53339 (5)	0.01703 (19)
C2	0.83551 (11)	0.06266 (6)	0.57353 (5)	0.0215 (2)
H2B	0.910124	0.031089	0.601141	0.026*
C3	0.69311 (11)	0.04690 (6)	0.57242 (6)	0.0228 (2)
H3A	0.671749	0.004190	0.599998	0.027*
C4	0.58049 (10)	0.09106 (6)	0.53259 (5)	0.0196 (2)
H4B	0.483773	0.078550	0.532377	0.024*
C5	0.61270 (10)	0.15408 (6)	0.49300 (5)	0.01704 (19)
O3	0.26881 (7)	0.17595 (5)	0.44883 (4)	0.02250 (16)
H3	0.3589 (19)	0.1824 (14)	0.4497 (13)	0.027*	0.61 (3)
O4	−0.19312 (7)	0.12596 (5)	0.35615 (4)	0.02344 (16)
H4	−0.2704 (15)	0.1017 (8)	0.3202 (7)	0.028*
N2	0.04226 (8)	0.14771 (5)	0.39488 (4)	0.01710 (16)
H2	0.0221 (13)	0.1564 (8)	0.4363 (6)	0.021*
C6	0.18169 (10)	0.15386 (6)	0.39087 (5)	0.01790 (19)
C7	0.21482 (11)	0.13432 (6)	0.32713 (6)	0.0213 (2)
H7	0.310669	0.137636	0.321914	0.026*
C8	0.10467 (11)	0.11005 (7)	0.27185 (6)	0.0239 (2)
H8	0.126899	0.095290	0.228771	0.029*
C9	−0.03761 (11)	0.10639 (6)	0.27684 (5)	0.0219 (2)
H9	−0.111893	0.090907	0.237695	0.026*
C10	−0.06756 (10)	0.12600 (6)	0.34062 (5)	0.01782 (19)
O5	1.10984 (8)	0.44209 (4)	0.77157 (4)	0.02427 (17)
O6	0.69473 (7)	0.46139 (4)	0.60703 (4)	0.02291 (16)
H6	0.633 (3)	0.4403 (16)	0.5726 (11)	0.027*	0.51 (3)
N3	0.90320 (8)	0.44362 (5)	0.68705 (4)	0.01738 (17)
H3B	0.8924 (13)	0.4921 (7)	0.7009 (7)	0.021*
C11	1.02185 (10)	0.40333 (6)	0.72324 (5)	0.01834 (19)
C12	1.03646 (12)	0.32439 (6)	0.70413 (6)	0.0254 (2)
H12	1.116169	0.293498	0.727941	0.030*
C13	0.93248 (13)	0.29207 (7)	0.64981 (6)	0.0295 (2)
H13	0.942521	0.238376	0.636833	0.035*
C14	0.81402 (11)	0.33486 (6)	0.61347 (6)	0.0240 (2)
H14	0.744993	0.311212	0.576036	0.029*
C15	0.79897 (10)	0.41320 (6)	0.63325 (5)	0.01727 (19)
O7	0.51409 (7)	0.40623 (4)	0.50930 (4)	0.02113 (15)
H7A	0.579 (3)	0.4265 (17)	0.5446 (12)	0.025*	0.49 (3)
O8	0.06505 (7)	0.32983 (5)	0.41128 (4)	0.02330 (16)
H8A	−0.0264 (13)	0.3226 (8)	0.4150 (7)	0.028*
N4	0.28349 (8)	0.37226 (5)	0.46665 (4)	0.01696 (17)
H4A	0.3118 (13)	0.3515 (8)	0.4316 (6)	0.020*
C16	0.38461 (10)	0.41017 (6)	0.51679 (5)	0.01732 (19)
C17	0.33735 (11)	0.44811 (6)	0.57103 (5)	0.0218 (2)
H17	0.402967	0.476182	0.606926	0.026*
C18	0.19353 (12)	0.44388 (7)	0.57127 (6)	0.0260 (2)
H18	0.161676	0.469269	0.608196	0.031*
C19	0.09332 (11)	0.40380 (7)	0.51941 (6)	0.0239 (2)
H19	−0.004815	0.401025	0.521012	0.029*
C20	0.14144 (10)	0.36826 (6)	0.46563 (5)	0.01835 (19)
O9	0.18597 (7)	0.69692 (4)	0.58239 (4)	0.02126 (15)
O10	0.66116 (7)	0.66705 (4)	0.66883 (4)	0.01849 (15)
H10	0.7367 (13)	0.6395 (8)	0.6998 (7)	0.022*
N5	0.42153 (8)	0.67871 (5)	0.63253 (4)	0.01655 (16)
H5	0.4396 (13)	0.7114 (7)	0.6004 (6)	0.020*
C21	0.28056 (10)	0.66605 (6)	0.63264 (5)	0.01715 (19)
C22	0.25389 (10)	0.61994 (6)	0.68815 (5)	0.0203 (2)
H22	0.158220	0.610105	0.691582	0.024*
C23	0.36839 (11)	0.58916 (6)	0.73752 (6)	0.0224 (2)
H23	0.349750	0.558253	0.775009	0.027*
C24	0.51056 (11)	0.60179 (6)	0.73441 (5)	0.0203 (2)
H24	0.587906	0.579291	0.768459	0.024*
C25	0.53506 (10)	0.64807 (6)	0.68018 (5)	0.01634 (18)
O11	0.64103 (7)	0.09175 (4)	0.75468 (4)	0.01983 (15)
O12	0.20548 (7)	0.07976 (5)	0.60556 (4)	0.02324 (16)
H12A	0.1306 (14)	0.1044 (8)	0.5774 (7)	0.028*
N6	0.42400 (8)	0.09381 (5)	0.67740 (4)	0.01662 (16)
H6A	0.4165 (13)	0.0440 (7)	0.6899 (7)	0.020*
C26	0.54837 (10)	0.13190 (6)	0.70929 (5)	0.01743 (19)
C27	0.56380 (12)	0.21052 (6)	0.68974 (6)	0.0260 (2)
H27	0.649710	0.238977	0.708997	0.031*
C28	0.45219 (13)	0.24630 (7)	0.64195 (6)	0.0304 (3)
H28	0.462424	0.300102	0.629325	0.036*
C29	0.32527 (12)	0.20661 (7)	0.61155 (6)	0.0249 (2)
H29	0.249173	0.232717	0.579442	0.030*
C30	0.31366 (10)	0.12804 (6)	0.62962 (5)	0.01851 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0114 (3)	0.0298 (4)	0.0185 (3)	0.0016 (3)	0.0002 (2)	0.0008 (3)
O2	0.0104 (3)	0.0268 (4)	0.0301 (4)	0.0005 (3)	0.0013 (3)	0.0117 (3)
N1	0.0118 (4)	0.0194 (4)	0.0174 (4)	−0.0001 (3)	0.0013 (3)	0.0032 (3)
C1	0.0133 (4)	0.0214 (5)	0.0148 (4)	0.0020 (3)	0.0000 (3)	−0.0032 (3)
C2	0.0195 (5)	0.0217 (5)	0.0210 (5)	0.0054 (4)	0.0002 (4)	0.0031 (4)
C3	0.0237 (5)	0.0199 (5)	0.0244 (5)	0.0007 (4)	0.0050 (4)	0.0050 (4)
C4	0.0157 (4)	0.0202 (5)	0.0229 (5)	−0.0015 (3)	0.0041 (4)	0.0014 (4)
C5	0.0127 (4)	0.0191 (4)	0.0181 (4)	0.0002 (3)	0.0013 (3)	−0.0003 (4)
O3	0.0113 (3)	0.0326 (4)	0.0218 (4)	−0.0029 (3)	0.0005 (3)	−0.0013 (3)
O4	0.0125 (3)	0.0331 (4)	0.0237 (4)	−0.0050 (3)	0.0022 (3)	−0.0064 (3)
N2	0.0123 (4)	0.0207 (4)	0.0177 (4)	−0.0014 (3)	0.0024 (3)	−0.0020 (3)
C6	0.0127 (4)	0.0177 (4)	0.0222 (5)	0.0001 (3)	0.0019 (3)	0.0020 (4)
C7	0.0164 (4)	0.0239 (5)	0.0247 (5)	0.0015 (4)	0.0069 (4)	0.0037 (4)
C8	0.0255 (5)	0.0271 (5)	0.0205 (5)	0.0003 (4)	0.0082 (4)	0.0002 (4)
C9	0.0205 (5)	0.0246 (5)	0.0187 (5)	−0.0031 (4)	0.0008 (4)	−0.0023 (4)
C10	0.0144 (4)	0.0167 (4)	0.0209 (5)	−0.0019 (3)	0.0011 (4)	−0.0001 (4)
O5	0.0181 (3)	0.0227 (4)	0.0261 (4)	0.0047 (3)	−0.0066 (3)	−0.0051 (3)
O6	0.0158 (3)	0.0241 (4)	0.0241 (4)	0.0013 (3)	−0.0048 (3)	−0.0018 (3)
N3	0.0143 (4)	0.0166 (4)	0.0193 (4)	0.0007 (3)	0.0001 (3)	−0.0023 (3)
C11	0.0146 (4)	0.0211 (5)	0.0179 (4)	0.0013 (3)	0.0010 (3)	0.0003 (4)
C12	0.0238 (5)	0.0218 (5)	0.0274 (5)	0.0069 (4)	−0.0004 (4)	−0.0019 (4)
C13	0.0319 (6)	0.0213 (5)	0.0319 (6)	0.0038 (4)	0.0007 (5)	−0.0073 (4)
C14	0.0225 (5)	0.0238 (5)	0.0227 (5)	−0.0027 (4)	−0.0002 (4)	−0.0059 (4)
C15	0.0133 (4)	0.0219 (5)	0.0158 (4)	−0.0022 (3)	0.0019 (3)	0.0006 (4)
O7	0.0119 (3)	0.0277 (4)	0.0218 (4)	−0.0025 (3)	0.0001 (3)	−0.0025 (3)
O8	0.0117 (3)	0.0300 (4)	0.0265 (4)	−0.0043 (3)	0.0012 (3)	−0.0042 (3)
N4	0.0128 (4)	0.0200 (4)	0.0176 (4)	−0.0006 (3)	0.0026 (3)	−0.0009 (3)
C16	0.0146 (4)	0.0174 (4)	0.0181 (4)	−0.0012 (3)	0.0001 (3)	0.0039 (3)
C17	0.0226 (5)	0.0223 (5)	0.0189 (5)	−0.0026 (4)	0.0020 (4)	−0.0014 (4)
C18	0.0267 (5)	0.0274 (5)	0.0261 (5)	−0.0009 (4)	0.0108 (4)	−0.0036 (4)
C19	0.0168 (4)	0.0271 (5)	0.0299 (5)	−0.0009 (4)	0.0093 (4)	−0.0003 (4)
C20	0.0134 (4)	0.0181 (4)	0.0224 (5)	−0.0010 (3)	0.0020 (4)	0.0037 (4)
O9	0.0110 (3)	0.0253 (4)	0.0252 (4)	−0.0008 (3)	−0.0002 (3)	0.0068 (3)
O10	0.0106 (3)	0.0242 (3)	0.0193 (3)	0.0011 (3)	0.0008 (2)	0.0022 (3)
N5	0.0120 (4)	0.0197 (4)	0.0171 (4)	0.0001 (3)	0.0017 (3)	0.0038 (3)
C21	0.0126 (4)	0.0175 (4)	0.0204 (5)	−0.0004 (3)	0.0020 (3)	−0.0008 (4)
C22	0.0152 (4)	0.0232 (5)	0.0237 (5)	−0.0004 (4)	0.0070 (4)	0.0016 (4)
C23	0.0236 (5)	0.0242 (5)	0.0207 (5)	0.0012 (4)	0.0077 (4)	0.0050 (4)
C24	0.0182 (5)	0.0231 (5)	0.0180 (5)	0.0041 (4)	0.0014 (4)	0.0036 (4)
C25	0.0132 (4)	0.0179 (4)	0.0168 (4)	0.0007 (3)	0.0013 (3)	−0.0022 (3)
O11	0.0143 (3)	0.0197 (3)	0.0214 (3)	−0.0014 (3)	−0.0040 (3)	0.0039 (3)
O12	0.0131 (3)	0.0304 (4)	0.0222 (4)	−0.0006 (3)	−0.0038 (3)	0.0036 (3)
N6	0.0130 (4)	0.0185 (4)	0.0166 (4)	0.0002 (3)	0.0000 (3)	0.0022 (3)
C26	0.0146 (4)	0.0203 (5)	0.0159 (4)	0.0001 (3)	0.0008 (3)	−0.0004 (4)
C27	0.0254 (5)	0.0202 (5)	0.0264 (5)	−0.0045 (4)	−0.0055 (4)	0.0018 (4)
C28	0.0369 (6)	0.0184 (5)	0.0291 (6)	−0.0001 (4)	−0.0058 (5)	0.0038 (4)
C29	0.0249 (5)	0.0234 (5)	0.0213 (5)	0.0067 (4)	−0.0045 (4)	0.0021 (4)
C30	0.0138 (4)	0.0254 (5)	0.0151 (4)	0.0031 (4)	0.0010 (3)	−0.0012 (4)

Geometric parameters (Å, º)

O1—C1	1.2875 (12)	O7—H7A	0.879 (18)
O2—H2A	0.839 (19)	O7—C16	1.2858 (12)
O2—C5	1.2956 (12)	O8—H8A	0.905 (12)
N1—H1	0.880 (12)	O8—C20	1.3098 (12)
N1—C1	1.3708 (12)	N4—H4A	0.868 (12)
N1—C5	1.3655 (12)	N4—C16	1.3630 (12)
C1—C2	1.3978 (15)	N4—C20	1.3590 (12)
C2—H2B	0.9500	C16—C17	1.4026 (15)
C2—C3	1.3859 (15)	C17—H17	0.9500
C3—H3A	0.9500	C17—C18	1.3819 (15)
C3—C4	1.3879 (14)	C18—H18	0.9500
C4—H4B	0.9500	C18—C19	1.3946 (15)
C4—C5	1.3908 (14)	C19—H19	0.9500
O3—H3	0.867 (17)	C19—C20	1.3811 (15)
O3—C6	1.2928 (12)	O9—C21	1.2789 (12)
O4—H4	0.981 (14)	O10—H10	0.948 (11)
O4—C10	1.3096 (12)	O10—C25	1.3193 (12)
N2—H2	0.888 (12)	N5—H5	0.882 (12)
N2—C6	1.3616 (12)	N5—C21	1.3688 (12)
N2—C10	1.3556 (12)	N5—C25	1.3557 (12)
C6—C7	1.3971 (15)	C21—C22	1.4067 (14)
C7—H7	0.9500	C22—H22	0.9500
C7—C8	1.3818 (15)	C22—C23	1.3795 (14)
C8—H8	0.9500	C23—H23	0.9500
C8—C9	1.3919 (15)	C23—C24	1.3952 (14)
C9—H9	0.9500	C24—H24	0.9500
C9—C10	1.3850 (15)	C24—C25	1.3805 (14)
O5—C11	1.2856 (12)	O11—C26	1.2884 (12)
O6—H6	0.861 (14)	O12—H12A	0.897 (12)
O6—C15	1.2949 (12)	O12—C30	1.3139 (12)
N3—H3B	0.874 (12)	N6—H6A	0.881 (12)
N3—C11	1.3686 (12)	N6—C26	1.3671 (12)
N3—C15	1.3672 (12)	N6—C30	1.3622 (12)
C11—C12	1.3966 (14)	C26—C27	1.3955 (14)
C12—H12	0.9500	C27—H27	0.9500
C12—C13	1.3843 (15)	C27—C28	1.3810 (15)
C13—H13	0.9500	C28—H28	0.9500
C13—C14	1.3896 (15)	C28—C29	1.3919 (16)
C14—H14	0.9500	C29—H29	0.9500
C14—C15	1.3916 (15)	C29—C30	1.3805 (15)
C5—O2—H2A	117 (3)	C16—O7—H7A	114.1 (19)
C1—N1—H1	117.4 (8)	C20—O8—H8A	111.5 (9)
C5—N1—H1	117.1 (8)	C16—N4—H4A	117.0 (8)
C5—N1—C1	125.31 (9)	C20—N4—H4A	118.0 (8)
O1—C1—N1	116.42 (9)	C20—N4—C16	124.96 (9)
O1—C1—C2	126.71 (9)	O7—C16—N4	115.79 (9)
N1—C1—C2	116.88 (9)	O7—C16—C17	127.13 (9)
C1—C2—H2B	120.5	N4—C16—C17	117.07 (9)
C3—C2—C1	118.94 (9)	C16—C17—H17	120.6
C3—C2—H2B	120.5	C18—C17—C16	118.75 (9)
C2—C3—H3A	118.7	C18—C17—H17	120.6
C2—C3—C4	122.58 (9)	C17—C18—H18	118.7
C4—C3—H3A	118.7	C17—C18—C19	122.56 (10)
C3—C4—H4B	120.8	C19—C18—H18	118.7
C3—C4—C5	118.37 (9)	C18—C19—H19	121.1
C5—C4—H4B	120.8	C20—C19—C18	117.81 (9)
O2—C5—N1	116.12 (9)	C20—C19—H19	121.1
O2—C5—C4	126.02 (9)	O8—C20—N4	113.69 (9)
N1—C5—C4	117.85 (9)	O8—C20—C19	127.49 (9)
C6—O3—H3	119.1 (16)	N4—C20—C19	118.83 (9)
C10—O4—H4	114.4 (8)	C25—O10—H10	111.5 (8)
C6—N2—H2	118.0 (8)	C25—N5—C21	124.86 (9)
C10—N2—H2	117.5 (8)	C21—N5—H5	117.3 (8)
C10—N2—C6	124.49 (9)	C25—N5—H5	117.8 (8)
O3—C6—N2	114.22 (9)	O9—C21—N5	117.12 (9)
O3—C6—C7	127.87 (9)	O9—C21—C22	126.28 (9)
N2—C6—C7	117.89 (9)	N5—C21—C22	116.60 (8)
C6—C7—H7	120.8	C21—C22—H22	120.4
C8—C7—C6	118.33 (9)	C23—C22—C21	119.17 (9)
C8—C7—H7	120.8	C23—C22—H22	120.4
C7—C8—H8	118.7	C22—C23—H23	118.8
C7—C8—C9	122.55 (10)	C22—C23—C24	122.38 (9)
C9—C8—H8	118.7	C24—C23—H23	118.8
C8—C9—H9	121.0	C23—C24—H24	121.1
C10—C9—C8	117.96 (9)	C25—C24—C23	117.76 (9)
C10—C9—H9	121.0	C25—C24—H24	121.1
O4—C10—N2	113.87 (9)	O10—C25—N5	114.23 (8)
O4—C10—C9	127.39 (9)	O10—C25—C24	126.58 (9)
N2—C10—C9	118.74 (9)	N5—C25—C24	119.19 (9)
C15—O6—H6	112.0 (19)	C30—O12—H12A	112.5 (9)
C11—N3—H3B	116.6 (8)	C26—N6—H6A	116.1 (8)
C15—N3—H3B	118.0 (8)	C30—N6—H6A	119.5 (8)
C15—N3—C11	125.33 (9)	C30—N6—C26	124.46 (9)
O5—C11—N3	116.65 (9)	O11—C26—N6	116.90 (9)
O5—C11—C12	126.15 (9)	O11—C26—C27	125.87 (9)
N3—C11—C12	117.21 (9)	N6—C26—C27	117.24 (9)
C11—C12—H12	120.7	C26—C27—H27	120.5
C13—C12—C11	118.67 (10)	C28—C27—C26	118.93 (10)
C13—C12—H12	120.7	C28—C27—H27	120.5
C12—C13—H13	118.6	C27—C28—H28	118.7
C12—C13—C14	122.76 (10)	C27—C28—C29	122.56 (10)
C14—C13—H13	118.6	C29—C28—H28	118.7
C13—C14—H14	120.8	C28—C29—H29	121.1
C13—C14—C15	118.38 (9)	C30—C29—C28	117.79 (9)
C15—C14—H14	120.8	C30—C29—H29	121.1
O6—C15—N3	115.11 (9)	O12—C30—N6	113.73 (9)
O6—C15—C14	127.23 (9)	O12—C30—C29	127.30 (9)
N3—C15—C14	117.65 (9)	N6—C30—C29	118.97 (9)
O1—C1—C2—C3	−179.28 (10)	O7—C16—C17—C18	−178.06 (10)
N1—C1—C2—C3	1.34 (14)	N4—C16—C17—C18	1.06 (14)
C1—N1—C5—O2	−177.46 (9)	C16—N4—C20—O8	178.71 (9)
C1—N1—C5—C4	2.61 (15)	C16—N4—C20—C19	−1.01 (15)
C1—C2—C3—C4	0.39 (16)	C16—C17—C18—C19	−0.44 (17)
C2—C3—C4—C5	−0.75 (16)	C17—C18—C19—C20	−0.91 (17)
C3—C4—C5—O2	179.42 (10)	C18—C19—C20—O8	−178.08 (10)
C3—C4—C5—N1	−0.66 (14)	C18—C19—C20—N4	1.60 (15)
C5—N1—C1—O1	177.61 (9)	C20—N4—C16—O7	178.86 (9)
C5—N1—C1—C2	−2.95 (14)	C20—N4—C16—C17	−0.35 (14)
O3—C6—C7—C8	178.33 (10)	O9—C21—C22—C23	178.40 (10)
N2—C6—C7—C8	0.10 (14)	N5—C21—C22—C23	−1.37 (14)
C6—N2—C10—O4	−178.47 (9)	C21—N5—C25—O10	178.72 (9)
C6—N2—C10—C9	1.86 (15)	C21—N5—C25—C24	−1.47 (15)
C6—C7—C8—C9	1.70 (16)	C21—C22—C23—C24	−0.27 (16)
C7—C8—C9—C10	−1.75 (16)	C22—C23—C24—C25	1.14 (16)
C8—C9—C10—O4	−179.62 (10)	C23—C24—C25—O10	179.46 (9)
C8—C9—C10—N2	0.00 (15)	C23—C24—C25—N5	−0.31 (15)
C10—N2—C6—O3	179.62 (9)	C25—N5—C21—O9	−177.48 (9)
C10—N2—C6—C7	−1.91 (15)	C25—N5—C21—C22	2.31 (14)
O5—C11—C12—C13	−178.89 (11)	O11—C26—C27—C28	−177.73 (11)
N3—C11—C12—C13	0.80 (16)	N6—C26—C27—C28	2.43 (16)
C11—N3—C15—O6	179.01 (9)	C26—N6—C30—O12	179.47 (9)
C11—N3—C15—C14	0.10 (15)	C26—N6—C30—C29	−0.36 (15)
C11—C12—C13—C14	−0.03 (19)	C26—C27—C28—C29	−1.01 (19)
C12—C13—C14—C15	−0.74 (18)	C27—C28—C29—C30	−1.18 (19)
C13—C14—C15—O6	−178.07 (11)	C28—C29—C30—O12	−177.96 (11)
C13—C14—C15—N3	0.70 (15)	C28—C29—C30—N6	1.84 (16)
C15—N3—C11—O5	178.86 (9)	C30—N6—C26—O11	178.32 (9)
C15—N3—C11—C12	−0.86 (15)	C30—N6—C26—C27	−1.83 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.84 (2)	1.60 (2)	2.4317 (10)	174 (4)
N1—H1···O9^i	0.88 (1)	1.98 (1)	2.8606 (11)	175 (1)
O3—H3···O2	0.87 (2)	1.57 (2)	2.4317 (10)	176 (3)
O4—H4···O5^ii	0.981 (14)	1.500 (14)	2.4768 (10)	173.5 (14)
N2—H2···O1^iii	0.89 (1)	1.89 (1)	2.7554 (11)	166 (1)
O6—H6···O7	0.86 (1)	1.58 (1)	2.4381 (10)	177 (3)
N3—H3B···O11^iv	0.87 (1)	1.95 (1)	2.8155 (11)	170 (1)
O7—H7A···O6	0.88 (2)	1.56 (2)	2.4381 (10)	179 (3)
O8—H8A···O9^v	0.91 (1)	1.58 (1)	2.4803 (10)	175 (1)
N4—H4A···O10^i	0.87 (1)	2.07 (1)	2.8999 (11)	161 (1)
O10—H10···O11^iv	0.95 (1)	1.52 (1)	2.4690 (9)	176 (1)
N5—H5···O2^i	0.88 (1)	1.90 (1)	2.7699 (11)	167 (1)
O12—H12A···O1^iii	0.90 (1)	1.61 (1)	2.5057 (10)	178 (2)
N6—H6A···O5^vi	0.88 (1)	1.91 (1)	2.7893 (11)	172 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−3/2, −y+1/2, z−1/2; (iii) x−1, y, z; (iv) −x+3/2, y+1/2, −z+3/2; (v) −x, −y+1, −z+1; (vi) −x+3/2, y−1/2, −z+3/2.