A redetermination of [N,N-bis(3,5-dimethyl-1H-pyrazol-1-ylmethyl-κN²)-2-hydroxyethyl­amine-κN](3,5-dimethyl-1H-pyrazole-κN²)nitratocopper(II) nitrate

The new crystal structure analysis of the title compound, [Cu(NO₃)(C₅H₈N₂)(C₁₄H₂₃N₅O)]NO₃, reveals that the copper(II) ion lies in a distorted octahedral environment, with four N atoms in the equatorial plane and two O atoms at the axial positions. The O atoms of the nitrate group are involved in intra- and intermolecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.010 Å
• Disorder in main residue
• R factor = 0.087
• wR factor = 0.231
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          3
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.73 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.69 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C92

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.130
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C72
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N8
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C91     ..       2.93 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              N O3

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C19 H31 Cu1 N9 O7
            Atom count from _chemical_formula_moiety:C19 H31 Cu1 N9 O5

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

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

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(3,5-dimethyl-1H-pyrazole-κN²)[N,N-bis(3,5-dimethyl-1H-pyrazol-1-ylmethyl- κN²)-2-hydroxyethylamine-κN]nitratocopper(II) nitrate

Crystal data

[Cu(NO3)(C5H8N2)(C14H23N5O)]NO3	Z = 2
Mr = 561.07	F(000) = 586
Triclinic, P1	Dx = 1.516 Mg m^−3
Hall symbol: -P 1	Melting point: 462 K
a = 8.351 (1) Å	Mo Kα radiation, λ = 0.71069 Å
b = 11.220 (1) Å	Cell parameters from 17830 reflections
c = 13.566 (1) Å	θ = 3.3–26.5°
α = 89.40 (1)°	µ = 0.95 mm^−1
β = 75.91 (1)°	T = 173 K
γ = 85.68 (1)°	Parallelepiped, blue
V = 1229.3 (2) Å^3	0.29 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	4170 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.130
Graphite monochromator	θmax = 26.6°, θmin = 3.3°
ω scans	h = −10→10
17830 measured reflections	k = −14→14
5106 independent reflections	l = −17→17

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.231	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0861P)^2 + 7.0572P] where P = (Fo^2 + 2Fc^2)/3
5106 reflections	(Δ/σ)max < 0.001
329 parameters	Δρmax = 1.25 e Å^−3
12 restraints	Δρmin = −0.74 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu	0.17247 (8)	0.26268 (6)	0.25884 (5)	0.0254 (2)
N4	0.0407 (6)	0.3976 (4)	0.2155 (3)	0.0245 (9)
N9	−0.1264 (6)	0.3975 (4)	0.2509 (4)	0.0256 (10)
H9	−0.1751	0.3492	0.2962	0.031*
N2	0.0689 (6)	0.1357 (4)	0.1992 (4)	0.0280 (10)
N8	−0.2004 (7)	0.1707 (5)	0.4205 (4)	0.0359 (12)
N1	0.0867 (6)	0.0277 (4)	0.2445 (4)	0.0289 (10)
N6	0.2405 (6)	0.3466 (5)	0.3690 (4)	0.0315 (11)
O6	−0.2946 (6)	0.2284 (5)	0.3752 (4)	0.0490 (13)
O5	−0.0722 (6)	0.2172 (5)	0.4279 (4)	0.0459 (12)
O7	−0.2326 (8)	0.0711 (5)	0.4542 (5)	0.0683 (17)
N7	0.5046 (11)	−0.2098 (6)	0.1195 (4)	0.061 (2)
O4	0.3787 (8)	−0.1793 (7)	0.0881 (5)	0.0746 (19)
O3	0.6370 (9)	−0.2445 (7)	0.0574 (5)	0.085 (2)
O21	0.5328 (16)	−0.1934 (10)	0.2061 (7)	0.064 (3)*	0.589 (14)
C61	0.1844 (8)	0.0145 (5)	0.3199 (5)	0.0343 (13)	0.589 (14)
H61A	0.2525	−0.0604	0.3088	0.041*	0.589 (14)
H61B	0.1115	0.0133	0.3875	0.041*	0.589 (14)
N31	0.2903 (6)	0.1150 (4)	0.3117 (4)	0.0373 (13)	0.589 (14)
C71	0.4650 (9)	0.1061 (8)	0.2569 (6)	0.022 (2)*	0.589 (14)
H71A	0.5176	0.0288	0.2680	0.026*	0.589 (14)
H71B	0.5231	0.1679	0.2798	0.026*	0.589 (14)
C81	0.4680 (12)	0.1222 (7)	0.1439 (6)	0.027 (2)*	0.589 (14)
H81A	0.5793	0.1056	0.1021	0.033*	0.589 (14)
H81B	0.3956	0.0687	0.1236	0.033*	0.589 (14)
O11	0.4094 (5)	0.2481 (4)	0.1333 (3)	0.0380 (10)	0.589 (14)
H11O	0.4059	0.2606	0.0741	0.057*
N51	0.3084 (6)	0.2693 (5)	0.4280 (4)	0.0379 (13)	0.589 (14)
C91	0.2874 (14)	0.1453 (7)	0.4229 (6)	0.027 (2)*	0.589 (14)
H91A	0.1827	0.1267	0.4676	0.032*	0.589 (14)
H91B	0.3759	0.0989	0.4439	0.032*	0.589 (14)
O22	0.4557 (15)	−0.2208 (10)	0.2144 (6)	0.035 (3)*	0.411 (14)
C62	0.1844 (8)	0.0145 (5)	0.3199 (5)	0.0343 (13)	0.411 (14)
H62A	0.2525	−0.0604	0.3088	0.041*	0.411 (14)
H62B	0.1115	0.0133	0.3875	0.041*	0.411 (14)
N32	0.2903 (6)	0.1150 (4)	0.3117 (4)	0.0373 (13)	0.411 (14)
C72	0.425 (2)	0.0736 (14)	0.2169 (11)	0.055 (5)*	0.411 (14)
H72A	0.4974	0.0126	0.2382	0.066*	0.411 (14)
H72B	0.3702	0.0351	0.1716	0.066*	0.411 (14)
C82	0.5338 (15)	0.1648 (12)	0.1542 (13)	0.041 (4)*	0.411 (14)
H82A	0.6008	0.2010	0.1932	0.049*	0.411 (14)
H82B	0.6048	0.1294	0.0925	0.049*	0.411 (14)
N52	0.3084 (6)	0.2693 (5)	0.4280 (4)	0.0379 (13)	0.411 (14)
O12	0.4094 (5)	0.2481 (4)	0.1333 (3)	0.0380 (10)	0.411 (14)
C92	0.361 (3)	0.1444 (12)	0.3971 (16)	0.068 (6)*	0.411 (14)
H92A	0.3225	0.0917	0.4537	0.082*	0.411 (14)
H92B	0.4808	0.1337	0.3765	0.082*	0.411 (14)
C1	0.0025 (11)	−0.1794 (6)	0.2504 (6)	0.054 (2)
H1A	0.1125	−0.2176	0.2308	0.082*
H1B	−0.0707	−0.2229	0.2221	0.082*
H1C	−0.0348	−0.1782	0.3232	0.082*
C2	0.0034 (8)	−0.0559 (5)	0.2122 (5)	0.0355 (14)
C3	−0.0716 (8)	0.0012 (6)	0.1420 (5)	0.0368 (14)
H3	−0.1393	−0.0326	0.1065	0.044*
C4	−0.0264 (7)	0.1187 (5)	0.1347 (5)	0.0302 (12)
C5	−0.0652 (10)	0.2130 (6)	0.0642 (6)	0.0458 (17)
H5A	−0.1626	0.2613	0.0978	0.069*
H5B	−0.0844	0.1761	0.0050	0.069*
H5C	0.0262	0.2622	0.0443	0.069*
C10	0.4171 (11)	0.2626 (12)	0.5833 (6)	0.082 (3)
H10A	0.3934	0.1801	0.5852	0.122*
H10B	0.3703	0.2987	0.6488	0.122*
H10C	0.5348	0.2681	0.5657	0.122*
C11	0.3435 (10)	0.3263 (9)	0.5055 (5)	0.057 (2)
C12	0.2963 (10)	0.4471 (9)	0.4959 (6)	0.058 (2)
H12	0.3060	0.5096	0.5381	0.069*
C13	0.2322 (8)	0.4552 (7)	0.4108 (5)	0.0378 (14)
C14	0.1644 (9)	0.5663 (6)	0.3706 (6)	0.0459 (17)
H14A	0.2351	0.5845	0.3060	0.069*
H14B	0.1587	0.6310	0.4173	0.069*
H14C	0.0554	0.5552	0.3626	0.069*
C15	0.2379 (8)	0.5137 (6)	0.0920 (5)	0.0360 (14)
H15A	0.3174	0.4764	0.1254	0.054*
H15B	0.2445	0.5987	0.0918	0.054*
H15C	0.2609	0.4846	0.0233	0.054*
C16	0.0683 (7)	0.4846 (5)	0.1473 (4)	0.0260 (11)
C17	−0.0861 (7)	0.5412 (5)	0.1397 (4)	0.0304 (12)
H17	−0.1027	0.6051	0.0982	0.037*
C18	−0.2058 (7)	0.4829 (5)	0.2060 (4)	0.0280 (12)
C19	−0.3901 (8)	0.4933 (6)	0.2270 (6)	0.0412 (15)
H19A	−0.4252	0.4379	0.1845	0.062*
H19B	−0.4276	0.5732	0.2130	0.062*
H19C	−0.4361	0.4753	0.2971	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0288 (4)	0.0201 (3)	0.0315 (4)	0.0014 (2)	−0.0165 (3)	0.0044 (2)
N4	0.027 (2)	0.024 (2)	0.025 (2)	0.0003 (18)	−0.0119 (19)	0.0027 (18)
N9	0.026 (2)	0.020 (2)	0.031 (2)	0.0017 (18)	−0.0081 (19)	0.0074 (18)
N2	0.032 (2)	0.017 (2)	0.037 (3)	0.0035 (18)	−0.015 (2)	0.0013 (18)
N8	0.036 (3)	0.040 (3)	0.033 (3)	−0.004 (2)	−0.012 (2)	0.013 (2)
N1	0.036 (3)	0.021 (2)	0.032 (2)	−0.0013 (19)	−0.012 (2)	0.0024 (19)
N6	0.030 (3)	0.039 (3)	0.029 (2)	−0.010 (2)	−0.014 (2)	0.010 (2)
O6	0.037 (2)	0.055 (3)	0.062 (3)	−0.008 (2)	−0.024 (2)	0.031 (3)
O5	0.033 (2)	0.062 (3)	0.047 (3)	0.002 (2)	−0.018 (2)	−0.007 (2)
O7	0.083 (4)	0.041 (3)	0.081 (4)	−0.009 (3)	−0.021 (3)	0.031 (3)
N7	0.106 (6)	0.041 (3)	0.029 (3)	0.029 (4)	−0.014 (3)	−0.004 (2)
O4	0.070 (4)	0.091 (5)	0.054 (4)	0.009 (4)	−0.002 (3)	0.008 (3)
O3	0.084 (5)	0.118 (6)	0.050 (4)	0.042 (4)	−0.025 (3)	−0.005 (4)
C61	0.037 (3)	0.025 (3)	0.044 (3)	0.001 (2)	−0.017 (3)	0.007 (2)
N31	0.029 (3)	0.028 (3)	0.061 (3)	−0.002 (2)	−0.025 (2)	0.021 (2)
O11	0.034 (2)	0.045 (3)	0.034 (2)	0.012 (2)	−0.0102 (19)	−0.0029 (19)
N51	0.026 (3)	0.060 (4)	0.031 (3)	−0.002 (2)	−0.015 (2)	0.016 (2)
C62	0.037 (3)	0.025 (3)	0.044 (3)	0.001 (2)	−0.017 (3)	0.007 (2)
N32	0.029 (3)	0.028 (3)	0.061 (3)	−0.002 (2)	−0.025 (2)	0.021 (2)
N52	0.026 (3)	0.060 (4)	0.031 (3)	−0.002 (2)	−0.015 (2)	0.016 (2)
O12	0.034 (2)	0.045 (3)	0.034 (2)	0.012 (2)	−0.0102 (19)	−0.0029 (19)
C1	0.072 (5)	0.029 (3)	0.061 (5)	−0.011 (3)	−0.009 (4)	−0.001 (3)
C2	0.033 (3)	0.025 (3)	0.046 (4)	−0.003 (2)	−0.003 (3)	−0.012 (3)
C3	0.032 (3)	0.036 (3)	0.044 (3)	−0.001 (3)	−0.010 (3)	−0.013 (3)
C4	0.028 (3)	0.029 (3)	0.036 (3)	0.005 (2)	−0.014 (2)	−0.009 (2)
C5	0.067 (5)	0.032 (3)	0.049 (4)	0.010 (3)	−0.038 (4)	−0.007 (3)
C10	0.056 (5)	0.157 (11)	0.035 (4)	0.020 (6)	−0.026 (4)	0.006 (5)
C11	0.045 (4)	0.102 (7)	0.026 (3)	0.010 (4)	−0.017 (3)	0.000 (4)
C12	0.048 (4)	0.088 (6)	0.040 (4)	0.016 (4)	−0.022 (3)	−0.026 (4)
C13	0.028 (3)	0.055 (4)	0.030 (3)	0.002 (3)	−0.007 (2)	−0.010 (3)
C14	0.045 (4)	0.042 (4)	0.053 (4)	0.007 (3)	−0.017 (3)	−0.023 (3)
C15	0.032 (3)	0.037 (3)	0.041 (3)	−0.001 (3)	−0.015 (3)	0.010 (3)
C16	0.031 (3)	0.024 (3)	0.026 (3)	0.000 (2)	−0.013 (2)	0.003 (2)
C17	0.034 (3)	0.028 (3)	0.031 (3)	0.005 (2)	−0.014 (2)	0.005 (2)
C18	0.032 (3)	0.023 (3)	0.030 (3)	0.007 (2)	−0.012 (2)	0.000 (2)
C19	0.027 (3)	0.042 (4)	0.054 (4)	0.002 (3)	−0.010 (3)	0.005 (3)

Geometric parameters (Å, º)

Cu—N4	1.973 (4)	C72—H72A	0.9700
Cu—N6	1.991 (5)	C72—H72B	0.9700
Cu—N2	1.995 (5)	C82—H82A	0.9700
Cu—N31	2.074 (5)	C82—H82B	0.9700
Cu—O5	2.747 (5)	C92—H92A	0.9700
Cu—O11	2.273 (5)	C92—H92B	0.9700
N4—C16	1.332 (7)	C1—C2	1.475 (9)
N4—N9	1.361 (6)	C1—H1A	0.9600
N9—C18	1.349 (7)	C1—H1B	0.9600
N9—H9	0.8600	C1—H1C	0.9600
N2—C4	1.342 (7)	C2—C3	1.387 (10)
N2—N1	1.367 (6)	C3—C4	1.395 (9)
N8—O7	1.227 (7)	C3—H3	0.9300
N8—O6	1.251 (7)	C4—C5	1.489 (9)
N8—O5	1.252 (7)	C5—H5A	0.9600
N1—C2	1.345 (8)	C5—H5B	0.9600
N1—C61	1.456 (8)	C5—H5C	0.9600
N6—C13	1.339 (8)	C10—C11	1.494 (10)
N6—N51	1.359 (7)	C10—H10A	0.9600
N7—O4	1.250 (9)	C10—H10B	0.9600
N7—O3	1.254 (9)	C10—H10C	0.9600
N7—O22	1.260 (8)	C11—C12	1.397 (13)
N7—O21	1.272 (8)	C12—C13	1.385 (9)
C61—N31	1.472 (8)	C12—H12	0.9300
C61—H61A	0.9700	C13—C14	1.483 (10)
C61—H61B	0.9700	C14—H14A	0.9600
N31—C71	1.463 (7)	C14—H14B	0.9600
N31—C91	1.543 (8)	C14—H14C	0.9600
C71—C81	1.535 (8)	C15—C16	1.490 (8)
C71—H71A	0.9700	C15—H15A	0.9600
C71—H71B	0.9700	C15—H15B	0.9600
C81—O11	1.478 (7)	C15—H15C	0.9600
C81—H81A	0.9700	C16—C17	1.420 (8)
C81—H81B	0.9700	C17—C18	1.373 (9)
O11—H11O	0.8200	C17—H17	0.9300
N51—C11	1.339 (9)	C18—C19	1.490 (8)
N51—C91	1.421 (8)	C19—H19A	0.9600
C91—H91A	0.9700	C19—H19B	0.9600
C91—H91B	0.9700	C19—H19C	0.9600
C72—C82	1.531 (10)
N4—Cu—N6	98.1 (2)	C82—C72—H72A	107.4
N4—Cu—N2	95.46 (18)	C82—C72—H72B	107.4
N6—Cu—N2	155.7 (2)	H72A—C72—H72B	106.9
N4—Cu—N31	174.67 (19)	C72—C82—H82A	111.8
N6—Cu—N31	82.9 (2)	C72—C82—H82B	111.8
N2—Cu—N31	81.79 (19)	H82A—C82—H82B	109.5
N4—Cu—O5	93.66 (17)	H92A—C92—H92B	108.3
N6—Cu—O5	77.25 (17)	C2—C1—H1A	109.5
N2—Cu—O5	81.82 (18)	C2—C1—H1B	109.5
N31—Cu—O5	81.46 (18)	H1A—C1—H1B	109.5
N4—Cu—O11	103.30 (17)	C2—C1—H1C	109.5
N6—Cu—O11	102.54 (19)	H1A—C1—H1C	109.5
N2—Cu—O11	93.82 (19)	H1B—C1—H1C	109.5
N31—Cu—O11	81.48 (18)	N1—C2—C3	105.4 (5)
C16—N4—N9	106.8 (4)	N1—C2—C1	122.5 (6)
C16—N4—Cu	136.6 (4)	C3—C2—C1	132.1 (6)
N9—N4—Cu	115.9 (3)	C2—C3—C4	107.2 (5)
C18—N9—N4	111.2 (4)	C2—C3—H3	126.4
C18—N9—H9	124.4	C4—C3—H3	126.4
N4—N9—H9	124.4	N2—C4—C3	109.4 (5)
C4—N2—N1	105.6 (5)	N2—C4—C5	122.8 (5)
C4—N2—Cu	142.4 (4)	C3—C4—C5	127.7 (5)
N1—N2—Cu	111.7 (3)	C4—C5—H5A	109.5
O7—N8—O6	120.4 (6)	C4—C5—H5B	109.5
O7—N8—O5	121.8 (6)	H5A—C5—H5B	109.5
O6—N8—O5	117.7 (5)	C4—C5—H5C	109.5
C2—N1—N2	112.3 (5)	H5A—C5—H5C	109.5
C2—N1—C61	127.7 (5)	H5B—C5—H5C	109.5
N2—N1—C61	120.0 (5)	C11—C10—H10A	109.5
C13—N6—N51	106.5 (5)	C11—C10—H10B	109.5
C13—N6—Cu	141.3 (4)	H10A—C10—H10B	109.5
N51—N6—Cu	112.0 (4)	C11—C10—H10C	109.5
N8—O5—Cu	121.2 (4)	H10A—C10—H10C	109.5
O4—N7—O3	119.8 (6)	H10B—C10—H10C	109.5
O4—N7—O22	106.3 (9)	N51—C11—C12	106.4 (6)
O3—N7—O22	132.1 (8)	N51—C11—C10	122.6 (9)
O4—N7—O21	129.6 (8)	C12—C11—C10	131.0 (8)
O3—N7—O21	109.4 (9)	C13—C12—C11	106.2 (7)
N1—C61—N31	109.4 (5)	C13—C12—H12	126.9
N1—C61—H61A	109.8	C11—C12—H12	126.9
N31—C61—H61A	109.8	N6—C13—C12	109.7 (7)
N1—C61—H61B	109.8	N6—C13—C14	124.4 (5)
N31—C61—H61B	109.8	C12—C13—C14	125.9 (7)
H61A—C61—H61B	108.2	C13—C14—H14A	109.5
C71—N31—C61	122.9 (6)	C13—C14—H14B	109.5
C71—N31—C91	105.9 (6)	H14A—C14—H14B	109.5
C61—N31—C91	104.2 (5)	C13—C14—H14C	109.5
C71—N31—Cu	108.6 (4)	H14A—C14—H14C	109.5
C61—N31—Cu	108.5 (3)	H14B—C14—H14C	109.5
C91—N31—Cu	105.5 (4)	C16—C15—H15A	109.5
N31—C71—C81	106.3 (6)	C16—C15—H15B	109.5
N31—C71—H71A	110.5	H15A—C15—H15B	109.5
C81—C71—H71A	110.5	C16—C15—H15C	109.5
N31—C71—H71B	110.5	H15A—C15—H15C	109.5
C81—C71—H71B	110.5	H15B—C15—H15C	109.5
H71A—C71—H71B	108.7	N4—C16—C17	108.9 (5)
O11—C81—C71	105.8 (6)	N4—C16—C15	122.8 (5)
O11—C81—H81A	110.6	C17—C16—C15	128.3 (5)
C71—C81—H81A	110.6	C18—C17—C16	106.3 (5)
O11—C81—H81B	110.6	C18—C17—H17	126.9
C71—C81—H81B	110.6	C16—C17—H17	126.9
H81A—C81—H81B	108.7	N9—C18—C17	106.8 (5)
C11—N51—N6	111.3 (6)	N9—C18—C19	120.6 (5)
C11—N51—C91	126.0 (6)	C17—C18—C19	132.4 (5)
N6—N51—C91	119.4 (5)	C18—C19—H19A	109.5
N51—C91—N31	107.6 (6)	C18—C19—H19B	109.5
N51—C91—H91A	110.2	H19A—C19—H19B	109.5
N31—C91—H91A	110.2	C18—C19—H19C	109.5
N51—C91—H91B	110.2	H19A—C19—H19C	109.5
N31—C91—H91B	110.2	H19B—C19—H19C	109.5
H91A—C91—H91B	108.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O6	0.86	1.91	2.756 (7)	169
O11—H11O···O3^i	0.82	1.92	2.708 (8)	162

Symmetry code: (i) −x+1, −y, −z.