Aqua­bis(N-benzoyl­alaninato-κO)(1,10-phenanthroline-κ²N,N′)­zinc(II)

In the title compound, [Zn(C₁₀H₁₀NO₃)₂(C₁₂H₈N₂)(H₂O)], the Zn^II atom is five-coordinated by the two N atoms of the 1,10-phenanthroline ligand, two O atoms from two benzoyl­alanine ligands and one O from a water mol­ecule. The complex exhibits a slightly distorted square-pyramidal geometry. The crystal structure is stabilized by hydrogen bonds of the types N—H...O, O—H...O and C—H...O.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.093
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C11     ..       5.94 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C15    -C20           1.37 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H6      ..       1.99 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.882(10) ......       3.00 su-Rat
              O7   -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.90(3), Rep   0.892(10) ......       3.00 su-Rat
              O7   -H4      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.88(3), Rep   0.882(10) ......       3.00 su-Rat
              O7   -H3      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(3), Rep   0.892(10) ......       3.00 su-Rat
              O7   -H4      1.555   1.555

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Aquabis(N-benzoylalaninato-κO)(1,10-phenanthroline-κ²N,N')zinc(II)

Crystal data

[Zn(C10H10NO3)2(C12H8N2)(H2O)]	F(000) = 1344
Mr = 647.99	Dx = 1.520 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4003 reflections
a = 10.005 (15) Å	θ = 2.5–22.8°
b = 29.38 (4) Å	µ = 0.93 mm^−1
c = 10.323 (16) Å	T = 298 K
β = 111.04 (2)°	Block, green
V = 2832 (7) Å^3	0.43 × 0.28 × 0.22 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	5060 independent reflections
Radiation source: fine-focus sealed tube	3472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.740, Tmax = 0.816	k = −35→23
11756 measured reflections	l = −12→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0418P)^2] where P = (Fo^2 + 2Fc^2)/3
5060 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.31 e Å^−3
3 restraints	Δρmin = −0.29 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.

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 > σ(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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.06115 (4)	0.028081 (11)	0.76220 (4)	0.03849 (13)
N1	0.2496 (3)	0.16422 (8)	0.7647 (2)	0.0340 (6)
H1	0.3411	0.1672	0.7938	0.041*
N2	−0.2412 (3)	0.13939 (8)	0.7813 (2)	0.0375 (6)
H2	−0.1492	0.1401	0.8147	0.045*
N3	0.2203 (3)	−0.02422 (8)	0.8368 (3)	0.0397 (6)
N4	0.1398 (3)	0.03904 (8)	0.9775 (3)	0.0417 (7)
O1	0.1715 (2)	0.07561 (7)	0.7119 (2)	0.0400 (5)
O2	0.0314 (3)	0.09066 (7)	0.4966 (2)	0.0659 (8)
O3	0.0516 (2)	0.16721 (7)	0.8156 (2)	0.0471 (6)
O4	−0.1126 (2)	0.06552 (7)	0.7489 (2)	0.0458 (6)
O5	−0.2789 (2)	0.04612 (8)	0.5480 (2)	0.0525 (6)
O6	−0.4416 (2)	0.16384 (9)	0.8044 (2)	0.0622 (7)
O7	−0.0651 (3)	−0.01138 (9)	0.6129 (3)	0.0618 (7)
C1	0.1199 (3)	0.10165 (10)	0.6092 (3)	0.0370 (7)
C2	0.1735 (3)	0.15037 (10)	0.6230 (3)	0.0346 (7)
H2A	0.0896	0.1702	0.5852	0.042*
C3	0.2657 (4)	0.15780 (14)	0.5379 (3)	0.0630 (11)
H3A	0.2977	0.1888	0.5470	0.095*
H3B	0.2113	0.1514	0.4422	0.095*
H3C	0.3472	0.1379	0.5700	0.095*
C4	0.1812 (3)	0.17247 (9)	0.8510 (3)	0.0339 (7)
C5	0.2667 (3)	0.18947 (9)	0.9928 (3)	0.0321 (7)
C6	0.4136 (3)	0.19404 (10)	1.0413 (3)	0.0412 (8)
H6	0.4645	0.1862	0.9848	0.049*
C7	0.4851 (4)	0.21011 (12)	1.1732 (4)	0.0548 (10)
H7	0.5842	0.2131	1.2054	0.066*
C8	0.4123 (4)	0.22165 (11)	1.2570 (3)	0.0514 (9)
H8	0.4617	0.2324	1.3462	0.062*
C9	0.2677 (4)	0.21748 (11)	1.2108 (3)	0.0513 (9)
H9	0.2178	0.2255	1.2680	0.062*
C10	0.1950 (4)	0.20127 (10)	1.0787 (3)	0.0442 (8)
H10	0.0959	0.1983	1.0475	0.053*
C11	−0.2274 (4)	0.07148 (11)	0.6494 (3)	0.0398 (8)
C12	−0.3117 (3)	0.11406 (10)	0.6543 (3)	0.0393 (8)
H12	−0.4054	0.1044	0.6543	0.047*
C13	−0.3370 (4)	0.14312 (12)	0.5273 (3)	0.0681 (12)
H13A	−0.3912	0.1696	0.5323	0.102*
H13B	−0.3892	0.1259	0.4457	0.102*
H13C	−0.2466	0.1524	0.5231	0.102*
C14	−0.3117 (3)	0.16127 (10)	0.8476 (3)	0.0365 (7)
C15	−0.2249 (3)	0.18142 (10)	0.9845 (3)	0.0342 (7)
C16	−0.1591 (3)	0.15288 (11)	1.0945 (3)	0.0423 (8)
H16	−0.1611	0.1216	1.0802	0.051*
C17	−0.0903 (4)	0.17012 (13)	1.2256 (3)	0.0539 (9)
H17	−0.0493	0.1506	1.3003	0.065*
C18	−0.0827 (4)	0.21601 (14)	1.2451 (4)	0.0592 (10)
H18	−0.0349	0.2278	1.3332	0.071*
C19	−0.1445 (4)	0.24463 (12)	1.1367 (4)	0.0596 (10)
H19	−0.1371	0.2759	1.1506	0.071*
C20	−0.2181 (4)	0.22744 (11)	1.0062 (4)	0.0502 (9)
H20	−0.2630	0.2471	0.9328	0.060*
C21	0.2616 (4)	−0.05480 (11)	0.7659 (4)	0.0498 (9)
H21	0.2091	−0.0580	0.6717	0.060*
C22	0.3800 (4)	−0.08244 (11)	0.8260 (4)	0.0564 (10)
H22	0.4056	−0.1038	0.7725	0.068*
C23	0.4578 (4)	−0.07819 (11)	0.9620 (4)	0.0559 (10)
H23	0.5376	−0.0966	1.0028	0.067*
C24	0.4190 (3)	−0.04624 (10)	1.0418 (4)	0.0420 (8)
C25	0.2978 (3)	−0.02003 (10)	0.9737 (3)	0.0369 (8)
C26	0.2555 (3)	0.01395 (10)	1.0497 (3)	0.0373 (8)
C27	0.3331 (3)	0.02059 (11)	1.1896 (3)	0.0425 (8)
C28	0.2881 (4)	0.05540 (13)	1.2556 (4)	0.0614 (11)
H28	0.3372	0.0613	1.3493	0.074*
C29	0.1723 (5)	0.08067 (13)	1.1827 (4)	0.0705 (12)
H29	0.1409	0.1038	1.2262	0.085*
C30	0.1019 (4)	0.07196 (12)	1.0447 (4)	0.0599 (11)
H30	0.0237	0.0900	0.9958	0.072*
C31	0.4958 (4)	−0.03871 (11)	1.1855 (4)	0.0510 (9)
H31	0.5761	−0.0563	1.2315	0.061*
C32	0.4548 (4)	−0.00683 (12)	1.2556 (4)	0.0504 (9)
H32	0.5072	−0.0026	1.3495	0.060*
H3	−0.146 (2)	0.0024 (9)	0.565 (3)	0.048 (11)*
H4	−0.043 (4)	−0.0343 (9)	0.567 (3)	0.092 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0393 (2)	0.0360 (2)	0.0360 (2)	0.00265 (18)	0.00849 (18)	−0.00082 (17)
N1	0.0253 (14)	0.0393 (14)	0.0331 (14)	−0.0071 (11)	0.0052 (12)	−0.0061 (11)
N2	0.0213 (14)	0.0465 (15)	0.0400 (15)	0.0012 (12)	0.0053 (13)	−0.0075 (12)
N3	0.0448 (17)	0.0314 (14)	0.0419 (16)	−0.0037 (13)	0.0142 (14)	0.0016 (12)
N4	0.0407 (17)	0.0431 (16)	0.0386 (16)	0.0111 (13)	0.0110 (14)	0.0027 (12)
O1	0.0310 (13)	0.0379 (12)	0.0429 (13)	0.0017 (10)	0.0034 (11)	0.0078 (10)
O2	0.0773 (19)	0.0410 (14)	0.0460 (15)	−0.0100 (13)	−0.0182 (14)	−0.0057 (12)
O3	0.0243 (13)	0.0635 (15)	0.0498 (14)	−0.0041 (11)	0.0088 (11)	−0.0075 (12)
O4	0.0333 (13)	0.0523 (14)	0.0399 (13)	0.0097 (11)	−0.0014 (11)	−0.0096 (11)
O5	0.0458 (15)	0.0579 (15)	0.0438 (14)	0.0016 (12)	0.0041 (12)	−0.0166 (12)
O6	0.0225 (13)	0.102 (2)	0.0557 (16)	0.0064 (13)	0.0067 (12)	−0.0249 (14)
O7	0.0488 (17)	0.0563 (16)	0.0658 (18)	0.0060 (14)	0.0027 (15)	−0.0256 (14)
C1	0.0318 (19)	0.0342 (17)	0.0417 (19)	0.0049 (15)	0.0091 (17)	−0.0024 (15)
C2	0.0337 (18)	0.0363 (17)	0.0276 (16)	0.0009 (14)	0.0033 (15)	−0.0007 (13)
C3	0.055 (2)	0.096 (3)	0.0333 (19)	−0.020 (2)	0.0102 (19)	−0.0071 (19)
C4	0.033 (2)	0.0295 (16)	0.0382 (18)	0.0010 (14)	0.0111 (16)	0.0006 (13)
C5	0.0312 (19)	0.0289 (15)	0.0342 (17)	−0.0015 (14)	0.0091 (15)	−0.0021 (13)
C6	0.034 (2)	0.051 (2)	0.0365 (19)	0.0008 (16)	0.0102 (16)	−0.0103 (15)
C7	0.037 (2)	0.072 (2)	0.048 (2)	−0.0075 (19)	0.0059 (18)	−0.0157 (19)
C8	0.057 (3)	0.057 (2)	0.035 (2)	0.0000 (19)	0.0093 (19)	−0.0119 (16)
C9	0.057 (3)	0.055 (2)	0.048 (2)	−0.0035 (19)	0.027 (2)	−0.0093 (17)
C10	0.037 (2)	0.052 (2)	0.045 (2)	−0.0044 (16)	0.0160 (17)	−0.0068 (16)
C11	0.036 (2)	0.047 (2)	0.0386 (19)	−0.0035 (16)	0.0155 (18)	−0.0035 (16)
C12	0.0304 (18)	0.0485 (19)	0.0335 (18)	0.0027 (15)	0.0048 (15)	−0.0027 (15)
C13	0.089 (3)	0.058 (2)	0.045 (2)	0.009 (2)	0.009 (2)	0.0026 (19)
C14	0.030 (2)	0.0426 (18)	0.0362 (18)	0.0043 (15)	0.0112 (16)	0.0037 (15)
C15	0.0240 (17)	0.0434 (19)	0.0347 (18)	0.0002 (14)	0.0100 (15)	−0.0030 (14)
C16	0.039 (2)	0.0435 (19)	0.042 (2)	0.0008 (16)	0.0113 (17)	0.0022 (15)
C17	0.047 (2)	0.070 (3)	0.040 (2)	0.0057 (19)	0.0109 (19)	0.0058 (19)
C18	0.040 (2)	0.083 (3)	0.048 (2)	0.004 (2)	0.0078 (19)	−0.021 (2)
C19	0.049 (2)	0.047 (2)	0.070 (3)	0.0014 (19)	0.006 (2)	−0.021 (2)
C20	0.043 (2)	0.044 (2)	0.055 (2)	0.0060 (17)	0.0083 (19)	0.0011 (17)
C21	0.064 (2)	0.0358 (19)	0.055 (2)	−0.0003 (18)	0.028 (2)	−0.0026 (16)
C22	0.061 (3)	0.041 (2)	0.076 (3)	0.0084 (19)	0.035 (2)	0.0017 (19)
C23	0.048 (2)	0.040 (2)	0.084 (3)	0.0119 (17)	0.030 (2)	0.014 (2)
C24	0.0318 (19)	0.0359 (17)	0.060 (2)	−0.0010 (15)	0.0179 (18)	0.0132 (16)
C25	0.0326 (19)	0.0326 (17)	0.046 (2)	−0.0014 (14)	0.0145 (17)	0.0087 (14)
C26	0.039 (2)	0.0338 (17)	0.0386 (19)	−0.0009 (15)	0.0130 (17)	0.0062 (14)
C27	0.037 (2)	0.047 (2)	0.0374 (19)	−0.0052 (16)	0.0069 (17)	0.0071 (16)
C28	0.069 (3)	0.071 (3)	0.035 (2)	0.011 (2)	0.008 (2)	−0.0014 (19)
C29	0.092 (3)	0.071 (3)	0.042 (2)	0.026 (2)	0.016 (2)	−0.009 (2)
C30	0.066 (3)	0.065 (2)	0.044 (2)	0.030 (2)	0.013 (2)	−0.0001 (19)
C31	0.034 (2)	0.050 (2)	0.058 (2)	0.0041 (17)	0.005 (2)	0.0229 (18)
C32	0.041 (2)	0.061 (2)	0.041 (2)	−0.0015 (19)	0.0048 (18)	0.0126 (18)

Geometric parameters (Å, º)

Zn1—O1	1.962 (3)	C10—H10	0.9300
Zn1—O7	1.979 (3)	C11—C12	1.519 (5)
Zn1—O4	2.020 (3)	C12—C13	1.507 (5)
Zn1—N4	2.100 (4)	C12—H12	0.9800
Zn1—N3	2.147 (3)	C13—H13A	0.9600
N1—C4	1.326 (4)	C13—H13B	0.9600
N1—C2	1.445 (4)	C13—H13C	0.9600
N1—H1	0.8600	C14—C15	1.490 (4)
N2—C14	1.313 (4)	C15—C20	1.368 (5)
N2—C12	1.452 (4)	C15—C16	1.374 (4)
N2—H2	0.8600	C16—C17	1.376 (5)
N3—C21	1.316 (4)	C16—H16	0.9300
N3—C25	1.351 (4)	C17—C18	1.361 (5)
N4—C30	1.323 (4)	C17—H17	0.9300
N4—C26	1.348 (4)	C18—C19	1.358 (5)
O1—C1	1.258 (4)	C18—H18	0.9300
O2—C1	1.225 (4)	C19—C20	1.379 (5)
O3—C4	1.224 (4)	C19—H19	0.9300
O4—C11	1.249 (4)	C20—H20	0.9300
O5—C11	1.237 (4)	C21—C22	1.386 (5)
O6—C14	1.216 (4)	C21—H21	0.9300
O7—H3	0.882 (10)	C22—C23	1.345 (5)
O7—H4	0.892 (10)	C22—H22	0.9300
C1—C2	1.517 (4)	C23—C24	1.393 (5)
C2—C3	1.501 (5)	C23—H23	0.9300
C2—H2A	0.9800	C24—C25	1.395 (4)
C3—H3A	0.9600	C24—C31	1.422 (5)
C3—H3B	0.9600	C25—C26	1.425 (4)
C3—H3C	0.9600	C26—C27	1.387 (5)
C4—C5	1.492 (4)	C27—C28	1.391 (5)
C5—C10	1.371 (4)	C27—C32	1.414 (5)
C5—C6	1.379 (4)	C28—C29	1.354 (5)
C6—C7	1.374 (4)	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.368 (5)
C7—C8	1.359 (5)	C29—H29	0.9300
C7—H7	0.9300	C30—H30	0.9300
C8—C9	1.357 (5)	C31—C32	1.335 (5)
C8—H8	0.9300	C31—H31	0.9300
C9—C10	1.380 (5)	C32—H32	0.9300
C9—H9	0.9300
O1—Zn1—O7	118.24 (14)	C13—C12—C11	111.1 (3)
O1—Zn1—O4	98.43 (14)	N2—C12—H12	107.6
O7—Zn1—O4	88.46 (13)	C13—C12—H12	107.6
O1—Zn1—N4	97.95 (11)	C11—C12—H12	107.6
O7—Zn1—N4	143.73 (12)	C12—C13—H13A	109.5
O4—Zn1—N4	88.56 (10)	C12—C13—H13B	109.5
O1—Zn1—N3	100.91 (15)	H13A—C13—H13B	109.5
O7—Zn1—N3	92.52 (14)	C12—C13—H13C	109.5
O4—Zn1—N3	157.45 (10)	H13A—C13—H13C	109.5
N4—Zn1—N3	77.40 (10)	H13B—C13—H13C	109.5
C4—N1—C2	121.4 (3)	O6—C14—N2	122.8 (3)
C4—N1—H1	119.3	O6—C14—C15	120.3 (3)
C2—N1—H1	119.3	N2—C14—C15	116.8 (3)
C14—N2—C12	123.0 (3)	C20—C15—C16	119.2 (3)
C14—N2—H2	118.5	C20—C15—C14	121.7 (3)
C12—N2—H2	118.5	C16—C15—C14	119.0 (3)
C21—N3—C25	117.8 (3)	C15—C16—C17	120.7 (3)
C21—N3—Zn1	129.0 (2)	C15—C16—H16	119.7
C25—N3—Zn1	112.5 (2)	C17—C16—H16	119.7
C30—N4—C26	117.5 (3)	C18—C17—C16	119.4 (3)
C30—N4—Zn1	126.7 (2)	C18—C17—H17	120.3
C26—N4—Zn1	115.0 (2)	C16—C17—H17	120.3
C1—O1—Zn1	123.8 (2)	C19—C18—C17	120.4 (3)
C11—O4—Zn1	130.4 (2)	C19—C18—H18	119.8
Zn1—O7—H3	111.5 (19)	C17—C18—H18	119.8
Zn1—O7—H4	130 (2)	C18—C19—C20	120.3 (3)
H3—O7—H4	114 (2)	C18—C19—H19	119.9
O2—C1—O1	125.3 (3)	C20—C19—H19	119.9
O2—C1—C2	116.6 (3)	C15—C20—C19	120.0 (3)
O1—C1—C2	118.1 (3)	C15—C20—H20	120.0
N1—C2—C3	109.9 (3)	C19—C20—H20	120.0
N1—C2—C1	113.6 (2)	N3—C21—C22	122.7 (3)
C3—C2—C1	110.7 (3)	N3—C21—H21	118.6
N1—C2—H2A	107.5	C22—C21—H21	118.6
C3—C2—H2A	107.5	C23—C22—C21	119.6 (3)
C1—C2—H2A	107.5	C23—C22—H22	120.2
C2—C3—H3A	109.5	C21—C22—H22	120.2
C2—C3—H3B	109.5	C22—C23—C24	120.0 (3)
H3A—C3—H3B	109.5	C22—C23—H23	120.0
C2—C3—H3C	109.5	C24—C23—H23	120.0
H3A—C3—H3C	109.5	C23—C24—C25	116.8 (3)
H3B—C3—H3C	109.5	C23—C24—C31	124.1 (3)
O3—C4—N1	121.5 (3)	C25—C24—C31	119.1 (3)
O3—C4—C5	120.6 (3)	N3—C25—C24	123.1 (3)
N1—C4—C5	117.9 (3)	N3—C25—C26	117.8 (3)
C10—C5—C6	118.6 (3)	C24—C25—C26	119.1 (3)
C10—C5—C4	118.0 (3)	N4—C26—C27	123.2 (3)
C6—C5—C4	123.4 (3)	N4—C26—C25	116.4 (3)
C7—C6—C5	120.1 (3)	C27—C26—C25	120.4 (3)
C7—C6—H6	120.0	C26—C27—C28	117.1 (3)
C5—C6—H6	120.0	C26—C27—C32	119.0 (3)
C8—C7—C6	120.6 (3)	C28—C27—C32	123.9 (3)
C8—C7—H7	119.7	C29—C28—C27	119.6 (3)
C6—C7—H7	119.7	C29—C28—H28	120.2
C9—C8—C7	120.1 (3)	C27—C28—H28	120.2
C9—C8—H8	120.0	C28—C29—C30	119.6 (4)
C7—C8—H8	120.0	C28—C29—H29	120.2
C8—C9—C10	119.7 (3)	C30—C29—H29	120.2
C8—C9—H9	120.1	N4—C30—C29	123.0 (3)
C10—C9—H9	120.1	N4—C30—H30	118.5
C5—C10—C9	120.9 (3)	C29—C30—H30	118.5
C5—C10—H10	119.5	C32—C31—C24	121.2 (3)
C9—C10—H10	119.5	C32—C31—H31	119.4
O5—C11—O4	126.3 (3)	C24—C31—H31	119.4
O5—C11—C12	117.2 (3)	C31—C32—C27	121.2 (3)
O4—C11—C12	116.5 (3)	C31—C32—H32	119.4
N2—C12—C13	111.8 (3)	C27—C32—H32	119.4
N2—C12—C11	110.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^i	0.86	2.14	2.968 (6)	162
N2—H2···O3	0.86	2.16	2.938 (5)	151
O7—H3···O5	0.88 (1)	1.81 (2)	2.617 (4)	151 (3)
O7—H4···O2^ii	0.89 (1)	1.80 (2)	2.663 (5)	161 (4)
C6—H6···O6^i	0.93	2.46	3.378 (6)	170
C17—H17···O2^iii	0.93	2.59	3.509 (7)	172
C21—H21···O2^ii	0.93	2.59	3.368 (7)	141
C30—H30···O4	0.93	2.53	3.043 (6)	115
C31—H31···O1^iv	0.93	2.45	3.293 (7)	152

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