Bis­(butane-2,3-dione monooxime benzoyl­hydrazone-κ³O,N,N′)­nickel(II) sulfate salicyl­hydro­xamic acid

The Ni atom in the title compound, [Ni(C₁₁H₁₃N₃O₂)₂]SO₄·C₇H₇NO₃, is O,N,N′-chelated by the two neutral hydrazone ligands in an octahedral environment. The cation interacts with the anion and the salicyl­hydro­xamic acid mol­ecule through hydrogen bonds to form a linear chain running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.059
• wR factor = 0.152
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.591     0.870
            Tmin' and Tmax expected:      0.751     0.866
            RR' =      0.783
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.61
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C14     ..       5.65 su
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         S1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      43.00 A   3  

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(butane-2,3-dione monooxime benzoylhydrazone-κ³O,N,N')nickel(II) sulfate salicylhydroxamic acid

Crystal data

[Ni(C11H13N3O2)2]SO4·C7H7NO3	F(000) = 1552
Mr = 746.39	Dx = 1.498 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21088 reflections
a = 7.986 (2) Å	θ = 3.1–27.4°
b = 23.781 (5) Å	µ = 0.72 mm^−1
c = 17.868 (4) Å	T = 295 K
β = 102.82 (3)°	Prism, yellow
V = 3309 (1) Å^3	0.39 × 0.27 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	7483 independent reflections
Radiation source: fine-focus sealed tube	4963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→10
Tmin = 0.591, Tmax = 0.870	k = −30→30
29244 measured reflections	l = −23→23

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 1.6714P] where P = (Fo^2 + 2Fc^2)/3
7483 reflections	(Δ/σ)max = 0.001
450 parameters	Δρmax = 1.19 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.80605 (5)	0.842363 (19)	0.82195 (2)	0.03235 (14)
S1	0.70492 (13)	0.69756 (4)	0.60396 (5)	0.0433 (2)
O1	0.9615 (4)	0.72360 (12)	0.78399 (16)	0.0552 (7)
H2o	0.9087	0.7324	0.7408	0.083*
O2	0.7425 (3)	0.92181 (10)	0.86001 (13)	0.0414 (6)
O3	0.4907 (4)	0.78890 (14)	0.87745 (15)	0.0576 (8)
H3o	0.5515	0.7964	0.9196	0.086*
O4	0.9934 (3)	0.87913 (11)	0.77353 (13)	0.0409 (6)
O5	0.8195 (4)	0.81190 (13)	0.49856 (17)	0.0613 (8)
H5o	0.7810	0.7852	0.5184	0.092*
O6	0.6192 (4)	0.90135 (13)	0.50373 (15)	0.0579 (8)
O7	0.5894 (4)	0.83629 (14)	0.28513 (16)	0.0653 (9)
H7O	0.5827	0.8326	0.2389	0.098*
O8	0.8144 (4)	0.74344 (12)	0.64345 (16)	0.0593 (8)
O9	0.5561 (4)	0.69058 (13)	0.63923 (16)	0.0598 (8)
O10	0.6483 (4)	0.71460 (13)	0.52294 (15)	0.0625 (8)
O11	0.8026 (4)	0.64516 (11)	0.60894 (15)	0.0535 (7)
N1	0.9428 (4)	0.76494 (12)	0.83487 (17)	0.0387 (7)
N2	0.9165 (3)	0.84054 (12)	0.93217 (15)	0.0335 (6)
N3	0.8789 (4)	0.88534 (12)	0.97441 (15)	0.0367 (7)
H3n	0.9106	0.8871	1.0236	0.044*
N4	0.5653 (4)	0.80900 (13)	0.82131 (17)	0.0390 (7)
N5	0.6905 (4)	0.84761 (12)	0.71125 (16)	0.0347 (6)
N6	0.7862 (4)	0.87300 (12)	0.66524 (16)	0.0368 (7)
H6n	0.7479	0.8786	0.6169	0.044*
N7	0.6970 (5)	0.83044 (15)	0.4353 (2)	0.0569 (9)
H7n	0.6811	0.8126	0.3924	0.068*
C1	1.1585 (6)	0.70861 (19)	0.9246 (3)	0.0616 (12)
H1a	1.1283	0.6884	0.9662	0.092*
H1b	1.2743	0.7221	0.9403	0.092*
H1c	1.1495	0.6840	0.8813	0.092*
C2	1.0395 (5)	0.75728 (16)	0.9030 (2)	0.0399 (8)
C3	1.0222 (4)	0.80126 (16)	0.9607 (2)	0.0384 (8)
C4	1.1218 (5)	0.79780 (19)	1.0409 (2)	0.0531 (10)
H4a	1.1037	0.8313	1.0680	0.080*
H4b	1.2417	0.7941	1.0413	0.080*
H4c	1.0846	0.7657	1.0655	0.080*
C5	0.7871 (4)	0.92659 (15)	0.93114 (19)	0.0352 (8)
C6	0.7506 (4)	0.97796 (14)	0.9718 (2)	0.0370 (8)
C7	0.8331 (5)	0.98884 (17)	1.0475 (2)	0.0474 (9)
H7	0.9094	0.9627	1.0748	0.057*
C8	0.8014 (6)	1.0387 (2)	1.0821 (3)	0.0631 (13)
H8	0.8573	1.0459	1.1326	0.076*
C9	0.6888 (7)	1.0773 (2)	1.0425 (3)	0.0698 (15)
H9	0.6679	1.1105	1.0663	0.084*
C10	0.6065 (6)	1.06710 (19)	0.9676 (3)	0.0665 (13)
H10	0.5297	1.0934	0.9409	0.080*
C11	0.6380 (5)	1.01742 (16)	0.9316 (2)	0.0503 (10)
H11	0.5835	1.0108	0.8808	0.060*
C12	0.2960 (5)	0.7763 (2)	0.7368 (2)	0.0572 (11)
H12a	0.2646	0.7682	0.7845	0.086*
H12b	0.3004	0.7419	0.7092	0.086*
H12c	0.2123	0.8010	0.7067	0.086*
C13	0.4678 (5)	0.80388 (16)	0.7524 (2)	0.0421 (9)
C14	0.5403 (5)	0.82797 (16)	0.6884 (2)	0.0414 (9)
C15	0.4409 (5)	0.82622 (19)	0.6079 (2)	0.0516 (10)
H15A	0.4912	0.8516	0.5773	0.077*
H15B	0.3244	0.8372	0.6060	0.077*
H15C	0.4426	0.7887	0.5882	0.077*
C16	0.9456 (5)	0.88822 (14)	0.7031 (2)	0.0363 (8)
C17	1.0642 (5)	0.91610 (15)	0.6611 (2)	0.0401 (8)
C18	1.0251 (5)	0.9233 (2)	0.5823 (2)	0.0554 (11)
H18	0.9217	0.9099	0.5531	0.067*
C19	1.1408 (6)	0.9509 (2)	0.5465 (3)	0.0667 (13)
H19	1.1139	0.9559	0.4936	0.080*
C20	1.2941 (7)	0.9704 (2)	0.5893 (3)	0.0688 (14)
H20	1.3710	0.9886	0.5653	0.083*
C21	1.3341 (7)	0.9632 (2)	0.6679 (3)	0.0807 (17)
H21	1.4373	0.9769	0.6969	0.097*
C22	1.2211 (6)	0.9356 (2)	0.7036 (3)	0.0650 (13)
H22	1.2499	0.9300	0.7564	0.078*
C23	0.4775 (5)	0.89414 (16)	0.3718 (2)	0.0435 (9)
C24	0.4704 (5)	0.87402 (18)	0.2968 (2)	0.0498 (10)
C25	0.3429 (7)	0.8931 (2)	0.2365 (3)	0.0751 (15)
H25	0.3396	0.8806	0.1869	0.090*
C26	0.2213 (8)	0.9305 (3)	0.2494 (3)	0.095 (2)
H26	0.1348	0.9424	0.2086	0.114*
C27	0.2260 (7)	0.9505 (2)	0.3221 (3)	0.0843 (17)
H27	0.1434	0.9758	0.3305	0.101*
C28	0.3534 (6)	0.9328 (2)	0.3820 (3)	0.0594 (11)
H28	0.3572	0.9470	0.4309	0.071*
C29	0.6044 (5)	0.87626 (17)	0.4420 (2)	0.0437 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0347 (2)	0.0393 (3)	0.0221 (2)	−0.0014 (2)	0.00413 (17)	0.00028 (18)
S1	0.0629 (6)	0.0426 (5)	0.0253 (4)	−0.0019 (5)	0.0118 (4)	−0.0015 (4)
O1	0.0632 (18)	0.0549 (18)	0.0466 (16)	0.0058 (14)	0.0102 (15)	−0.0148 (14)
O2	0.0501 (14)	0.0412 (14)	0.0305 (13)	0.0043 (12)	0.0040 (11)	0.0020 (11)
O3	0.0601 (17)	0.080 (2)	0.0325 (14)	−0.0089 (16)	0.0109 (14)	0.0063 (15)
O4	0.0410 (13)	0.0523 (16)	0.0282 (13)	−0.0077 (12)	0.0048 (11)	−0.0013 (11)
O5	0.074 (2)	0.058 (2)	0.0466 (17)	0.0033 (16)	0.0029 (16)	0.0146 (14)
O6	0.0664 (18)	0.075 (2)	0.0327 (14)	0.0036 (16)	0.0117 (14)	−0.0071 (14)
O7	0.085 (2)	0.078 (2)	0.0353 (15)	0.0249 (18)	0.0172 (16)	−0.0028 (15)
O8	0.078 (2)	0.0497 (17)	0.0509 (17)	−0.0123 (15)	0.0167 (16)	−0.0117 (14)
O9	0.0622 (18)	0.076 (2)	0.0450 (17)	−0.0018 (15)	0.0191 (15)	0.0099 (14)
O10	0.101 (2)	0.0599 (19)	0.0250 (13)	0.0106 (17)	0.0096 (15)	0.0033 (12)
O11	0.080 (2)	0.0462 (16)	0.0365 (14)	0.0060 (14)	0.0182 (14)	0.0019 (12)
N1	0.0408 (16)	0.0411 (17)	0.0363 (16)	−0.0014 (13)	0.0130 (14)	−0.0035 (13)
N2	0.0367 (14)	0.0355 (15)	0.0271 (14)	−0.0031 (13)	0.0045 (12)	−0.0037 (12)
N3	0.0482 (17)	0.0377 (16)	0.0229 (14)	−0.0010 (13)	0.0048 (13)	−0.0029 (12)
N4	0.0395 (16)	0.0457 (18)	0.0336 (16)	0.0005 (14)	0.0117 (14)	0.0019 (13)
N5	0.0361 (15)	0.0419 (17)	0.0265 (14)	−0.0041 (13)	0.0080 (12)	−0.0002 (12)
N6	0.0425 (16)	0.0445 (17)	0.0234 (14)	−0.0044 (14)	0.0073 (13)	0.0017 (12)
N7	0.079 (2)	0.050 (2)	0.0362 (18)	0.0103 (18)	0.0015 (18)	0.0008 (15)
C1	0.067 (3)	0.061 (3)	0.055 (3)	0.026 (2)	0.009 (2)	0.005 (2)
C2	0.0391 (19)	0.044 (2)	0.0361 (19)	0.0029 (16)	0.0074 (16)	0.0024 (16)
C3	0.0368 (18)	0.046 (2)	0.0313 (18)	0.0013 (16)	0.0049 (15)	0.0042 (16)
C4	0.054 (2)	0.065 (3)	0.033 (2)	0.011 (2)	−0.0044 (19)	0.0022 (19)
C5	0.0372 (18)	0.0382 (19)	0.0302 (18)	−0.0062 (15)	0.0073 (15)	0.0009 (15)
C6	0.0417 (19)	0.0352 (19)	0.0373 (19)	−0.0028 (15)	0.0159 (16)	−0.0017 (15)
C7	0.046 (2)	0.049 (2)	0.047 (2)	−0.0035 (18)	0.0103 (19)	−0.0064 (18)
C8	0.072 (3)	0.059 (3)	0.066 (3)	−0.023 (2)	0.032 (3)	−0.029 (2)
C9	0.091 (4)	0.041 (3)	0.093 (4)	−0.011 (3)	0.053 (3)	−0.018 (3)
C10	0.077 (3)	0.042 (2)	0.092 (4)	0.012 (2)	0.042 (3)	0.010 (3)
C11	0.056 (2)	0.041 (2)	0.055 (2)	0.0015 (19)	0.015 (2)	0.0045 (19)
C12	0.044 (2)	0.082 (3)	0.042 (2)	−0.013 (2)	0.0016 (19)	0.006 (2)
C13	0.0391 (19)	0.049 (2)	0.039 (2)	0.0027 (17)	0.0099 (17)	−0.0007 (17)
C14	0.047 (2)	0.045 (2)	0.0317 (18)	0.0031 (17)	0.0086 (17)	−0.0006 (15)
C15	0.048 (2)	0.070 (3)	0.032 (2)	−0.005 (2)	−0.0001 (18)	−0.0004 (19)
C16	0.0423 (19)	0.0356 (19)	0.0315 (18)	−0.0031 (15)	0.0089 (16)	−0.0049 (14)
C17	0.049 (2)	0.038 (2)	0.0371 (19)	−0.0028 (17)	0.0169 (17)	−0.0020 (16)
C18	0.049 (2)	0.077 (3)	0.043 (2)	−0.002 (2)	0.0140 (19)	0.010 (2)
C19	0.069 (3)	0.079 (3)	0.060 (3)	0.006 (3)	0.032 (3)	0.022 (3)
C20	0.085 (3)	0.062 (3)	0.073 (3)	−0.024 (3)	0.049 (3)	−0.006 (2)
C21	0.084 (3)	0.094 (4)	0.074 (3)	−0.054 (3)	0.038 (3)	−0.028 (3)
C22	0.074 (3)	0.078 (3)	0.048 (2)	−0.034 (3)	0.022 (2)	−0.019 (2)
C23	0.052 (2)	0.045 (2)	0.0348 (19)	−0.0057 (18)	0.0136 (18)	0.0024 (16)
C24	0.055 (2)	0.056 (3)	0.039 (2)	0.003 (2)	0.0120 (19)	0.0017 (19)
C25	0.089 (4)	0.095 (4)	0.037 (2)	0.028 (3)	0.003 (2)	−0.001 (2)
C26	0.095 (4)	0.131 (5)	0.053 (3)	0.051 (4)	0.001 (3)	0.008 (3)
C27	0.078 (3)	0.103 (4)	0.071 (4)	0.037 (3)	0.016 (3)	−0.003 (3)
C28	0.062 (3)	0.069 (3)	0.050 (3)	0.006 (2)	0.018 (2)	−0.005 (2)
C29	0.051 (2)	0.050 (2)	0.0324 (19)	−0.0083 (19)	0.0138 (17)	0.0026 (17)

Geometric parameters (Å, º)

Ni1—O2	2.108 (2)	C6—C11	1.385 (5)
Ni1—O4	2.080 (2)	C6—C7	1.390 (5)
Ni1—N1	2.127 (3)	C7—C8	1.386 (6)
Ni1—N2	1.972 (3)	C7—H7	0.9300
Ni1—N5	1.992 (3)	C8—C9	1.367 (7)
Ni1—N4	2.078 (3)	C8—H8	0.9300
S1—O8	1.476 (3)	C9—C10	1.376 (7)
S1—O9	1.473 (3)	C9—H9	0.9300
S1—O10	1.474 (3)	C10—C11	1.394 (6)
S1—O11	1.462 (3)	C10—H10	0.9300
O1—N1	1.369 (4)	C11—H11	0.9300
O1—H2o	0.8200	C12—C13	1.490 (5)
O2—C5	1.247 (4)	C12—H12a	0.9600
O3—N4	1.362 (4)	C12—H12b	0.9600
O3—H3o	0.8200	C12—H12c	0.9600
O4—C16	1.250 (4)	C13—C14	1.504 (5)
O5—N7	1.392 (4)	C14—C15	1.482 (5)
O5—H5o	0.8200	C15—H15a	0.9600
O6—C29	1.236 (4)	C15—H15b	0.9600
O7—C24	1.357 (5)	C15—H15c	0.9600
O7—H7O	0.8200	C16—C17	1.488 (5)
N1—C2	1.302 (5)	C17—C18	1.383 (5)
N2—C3	1.286 (4)	C17—C22	1.393 (6)
N2—N3	1.377 (4)	C18—C19	1.398 (6)
N3—C5	1.359 (4)	C18—H18	0.9300
N3—H3n	0.8600	C19—C20	1.372 (7)
N4—C13	1.308 (5)	C19—H19	0.9300
N5—C14	1.267 (5)	C20—C21	1.381 (7)
N5—N6	1.379 (4)	C20—H20	0.9300
N6—C16	1.352 (5)	C21—C22	1.380 (6)
N6—H6n	0.8600	C21—H21	0.9300
N7—C29	1.337 (5)	C22—H22	0.9300
N7—H7n	0.8600	C23—C28	1.393 (6)
C1—C2	1.493 (5)	C23—C24	1.411 (5)
C1—H1a	0.9600	C23—C29	1.490 (5)
C1—H1b	0.9600	C24—C25	1.385 (6)
C1—H1c	0.9600	C25—C26	1.372 (7)
C2—C3	1.497 (5)	C25—H25	0.9300
C3—C4	1.479 (5)	C26—C27	1.376 (7)
C4—H4a	0.9600	C26—H26	0.9300
C4—H4b	0.9600	C27—C28	1.369 (7)
C4—H4c	0.9600	C27—H27	0.9300
C5—C6	1.483 (5)	C28—H28	0.9300
O2—Ni1—O4	90.3 (1)	C6—C7—H7	120.0
O2—Ni1—N1	153.6 (1)	C9—C8—C7	120.5 (5)
O2—Ni1—N2	77.5 (1)	C9—C8—H8	119.7
O2—Ni1—N4	93.2 (1)	C7—C8—H8	119.7
O2—Ni1—N5	99.9 (1)	C8—C9—C10	120.1 (4)
O4—Ni1—N1	90.6 (1)	C8—C9—H9	119.9
O4—Ni1—N2	102.8 (1)	C10—C9—H9	119.9
O4—Ni1—N4	155.3 (1)	C9—C10—C11	120.1 (5)
O4—Ni1—N5	77.2 (1)	C9—C10—H10	119.9
N1—Ni1—N2	76.6 (1)	C11—C10—H10	119.9
N1—Ni1—N4	97.0 (1)	C6—C11—C10	119.9 (4)
N1—Ni1—N5	106.0 (1)	C6—C11—H11	120.1
N2—Ni1—N4	101.9 (1)	C10—C11—H11	120.1
N2—Ni1—N5	177.5 (1)	C13—C12—H12a	109.5
N4—Ni1—N5	78.1 (1)	C13—C12—H12b	109.5
O8—S1—O9	109.1 (2)	H12a—C12—H12b	109.5
O8—S1—O10	106.6 (2)	C13—C12—H12c	109.5
O8—S1—O11	110.5 (2)	H12a—C12—H12c	109.5
O9—S1—O10	110.5 (2)	H12b—C12—H12c	109.5
O9—S1—O11	110.4 (2)	N4—C13—C12	123.2 (3)
O10—S1—O11	109.7 (2)	N4—C13—C14	115.5 (3)
N1—O1—H2o	109.5	C12—C13—C14	121.3 (3)
C5—O2—Ni1	112.1 (2)	N5—C14—C15	126.0 (3)
N4—O3—H3o	109.5	N5—C14—C13	113.1 (3)
C16—O4—Ni1	113.9 (2)	C15—C14—C13	120.9 (3)
N7—O5—H5o	109.5	C14—C15—H15a	109.5
C24—O7—H7O	109.5	C14—C15—H15b	109.5
C2—N1—O1	113.0 (3)	H15a—C15—H15b	109.5
C2—N1—Ni1	114.0 (2)	C14—C15—H15c	109.5
O1—N1—Ni1	132.7 (2)	H15a—C15—H15c	109.5
C3—N2—N3	123.3 (3)	H15b—C15—H15c	109.5
C3—N2—Ni1	121.4 (2)	O4—C16—N6	120.0 (3)
N3—N2—Ni1	115.3 (2)	O4—C16—C17	119.9 (3)
C5—N3—N2	113.7 (3)	N6—C16—C17	120.1 (3)
C5—N3—H3n	123.1	C18—C17—C22	119.0 (4)
N2—N3—H3n	123.1	C18—C17—C16	122.9 (4)
C13—N4—O3	113.2 (3)	C22—C17—C16	118.0 (3)
C13—N4—Ni1	113.4 (2)	C17—C18—C19	120.1 (4)
O3—N4—Ni1	133.3 (2)	C17—C18—H18	120.0
C14—N5—N6	125.4 (3)	C19—C18—H18	120.0
C14—N5—Ni1	119.5 (2)	C20—C19—C18	120.2 (4)
N6—N5—Ni1	115.1 (2)	C20—C19—H19	119.9
C16—N6—N5	113.8 (3)	C18—C19—H19	119.9
C16—N6—H6n	123.1	C19—C20—C21	120.0 (4)
N5—N6—H6n	123.1	C19—C20—H20	120.0
C29—N7—O5	119.2 (3)	C21—C20—H20	120.0
C29—N7—H7n	120.4	C22—C21—C20	120.1 (5)
O5—N7—H7n	120.4	C22—C21—H21	120.0
C2—C1—H1a	109.5	C20—C21—H21	120.0
C2—C1—H1b	109.5	C21—C22—C17	120.6 (4)
H1a—C1—H1b	109.5	C21—C22—H22	119.7
C2—C1—H1c	109.5	C17—C22—H22	119.7
H1a—C1—H1c	109.5	C28—C23—C24	117.9 (4)
H1b—C1—H1c	109.5	C28—C23—C29	116.6 (3)
N1—C2—C1	124.2 (3)	C24—C23—C29	125.4 (4)
N1—C2—C3	114.8 (3)	O7—C24—C25	121.1 (4)
C1—C2—C3	121.0 (3)	O7—C24—C23	119.2 (4)
N2—C3—C4	126.1 (3)	C25—C24—C23	119.6 (4)
N2—C3—C2	112.8 (3)	C26—C25—C24	120.5 (4)
C4—C3—C2	121.1 (3)	C26—C25—H25	119.7
C3—C4—H4a	109.5	C24—C25—H25	119.7
C3—C4—H4b	109.5	C25—C26—C27	120.6 (5)
H4a—C4—H4b	109.5	C25—C26—H26	119.7
C3—C4—H4c	109.5	C27—C26—H26	119.7
H4a—C4—H4c	109.5	C28—C27—C26	119.5 (5)
H4b—C4—H4c	109.5	C28—C27—H27	120.3
O2—C5—N3	120.7 (3)	C26—C27—H27	120.3
O2—C5—C6	122.1 (3)	C27—C28—C23	121.8 (4)
N3—C5—C6	117.1 (3)	C27—C28—H28	119.1
C11—C6—C7	119.4 (4)	C23—C28—H28	119.1
C11—C6—C5	118.7 (3)	O6—C29—N7	121.9 (4)
C7—C6—C5	121.8 (3)	O6—C29—C23	121.7 (4)
C8—C7—C6	119.9 (4)	N7—C29—C23	116.3 (3)
C8—C7—H7	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2o···O8	0.82	1.76	2.569 (4)	171
O3—H3o···O10^i	0.82	1.86	2.626 (4)	156
N3—H3n···O11^i	0.86	2.06	2.707 (4)	132
N6—H6n···O6	0.86	2.13	2.975 (4)	170
O5—H5o···O10	0.82	2.00	2.771 (4)	157
O7—H7o···O9^ii	0.82	1.83	2.639 (4)	168
N7—H7n···O7	0.86	1.98	2.634 (5)	132

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