(S)-2-Hydr­oxy-2-phenyl­acetic acid–(R)-2-amino­butanoic acid–water (1/1/0.5)

The title complex, C₈H₆O₃·C₄H₈NO₂·0.5H₂O, was obtained from an aqueous solution of racemic 2-amino­butyric acid and (S)-2-hydroxy­phenyl­acetic acid. In the crystal structure, a two-dimensional network is formed via O—H...O [H...O = 1.63 (5)–2.52 (5) Å] and N—H...O [H...O = 1.91 (4)–2.30 (4) Å] hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.104
• Data-to-parameter ratio = 7.8

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:      0.748     0.980
            Tmin(prime) and Tmax expected:      0.949     0.983
            RR(prime) =      0.791
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.104
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.82
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.61 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       5.60 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N2     -   H16    ...       1.02 Ang.

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:   C24 H36 N2 O11
            Atom count from _chemical_formula_moiety:C12 H18 N1 O5.5
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               3134
           Count of symmetry unique reflns         3158
           Completeness (_total/calc)             99.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
  10 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(S)-2-Hydroxy-2-phenylacetic acid–(R)-2-aminobutanoic acid–water (1/1/2)

Crystal data

C8H8O3·C4H9NO2·0.5H2O	F(000) = 564
Mr = 264.28	Dx = 1.301 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2567 reflections
a = 6.0017 (7) Å	θ = 5.1–47.2°
b = 8.4357 (9) Å	µ = 0.10 mm^−1
c = 26.733 (3) Å	T = 293 K
β = 94.614 (2)°	Prism, colorless
V = 1349.0 (3) Å^3	0.50 × 0.47 × 0.17 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer	3134 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.748, Tmax = 0.980	k = −8→10
8010 measured reflections	l = −34→34

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0478P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max = 0.027
3134 reflections	Δρmax = 0.24 e Å^−3
401 parameters	Δρmin = −0.19 e Å^−3
3 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)

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
O1	0.4186 (3)	0.8232 (2)	0.28496 (8)	0.0494 (5)
O2	0.2602 (3)	1.0191 (3)	0.32406 (8)	0.0557 (6)
O3	0.9807 (4)	0.3209 (3)	0.30162 (8)	0.0568 (6)
O4	1.2453 (4)	0.2941 (3)	0.36424 (8)	0.0532 (6)
O5	0.9632 (5)	0.6353 (3)	0.31287 (9)	0.0712 (8)
O6	0.6110 (3)	0.1284 (2)	0.20869 (7)	0.0468 (5)
O7	0.7728 (3)	0.3246 (3)	0.17047 (8)	0.0480 (5)
O8	0.0585 (4)	0.6155 (2)	0.20827 (8)	0.0562 (6)
O9	−0.2254 (4)	0.6137 (3)	0.14912 (9)	0.0604 (6)
O10	0.1068 (4)	0.9291 (3)	0.20287 (8)	0.0534 (6)
O11	0.5037 (5)	0.4796 (4)	0.27371 (10)	0.0669 (6)
N1	0.8152 (4)	0.9645 (4)	0.29053 (9)	0.0385 (5)
N2	0.2207 (4)	0.2697 (4)	0.20649 (9)	0.0394 (5)
C1	0.4247 (4)	0.9466 (3)	0.30970 (10)	0.0343 (6)
C2	0.6534 (4)	1.0175 (3)	0.32595 (9)	0.0323 (6)
C3	0.7400 (5)	0.9652 (5)	0.37903 (10)	0.0544 (8)
H3A	0.7451	0.8503	0.3799	0.065*
H3B	0.8919	1.0035	0.3857	0.065*
C4	0.6045 (7)	1.0216 (5)	0.41995 (12)	0.0736 (11)
H4A	0.5913	1.1350	0.4184	0.110*
H4B	0.6766	0.9914	0.4519	0.110*
H4C	0.4583	0.9748	0.4159	0.110*
C5	1.0989 (5)	0.3769 (4)	0.33595 (10)	0.0421 (7)
C6	1.0905 (5)	0.5488 (4)	0.35099 (11)	0.0465 (7)
C7	0.9809 (5)	0.5704 (4)	0.39961 (10)	0.0433 (6)
C8	1.0834 (6)	0.6657 (4)	0.43707 (13)	0.0624 (9)
H8	1.2218	0.7114	0.4330	0.075*
C9	0.9784 (8)	0.6920 (6)	0.48029 (14)	0.0790 (12)
H9	1.0458	0.7568	0.5053	0.095*
C10	0.7798 (9)	0.6251 (6)	0.48669 (14)	0.0878 (14)
H10	0.7115	0.6439	0.5161	0.105*
C11	0.6754 (7)	0.5285 (5)	0.45015 (14)	0.0731 (11)
H11	0.5384	0.4818	0.4549	0.088*
C12	0.7786 (5)	0.5025 (4)	0.40614 (11)	0.0513 (8)
H12	0.7097	0.4387	0.3811	0.062*
C13	0.6064 (4)	0.2528 (3)	0.18530 (9)	0.0323 (5)
C14	0.3776 (4)	0.3250 (3)	0.17014 (9)	0.0319 (5)
C15	0.2879 (5)	0.2765 (4)	0.11751 (10)	0.0506 (7)
H15A	0.2863	0.1617	0.1154	0.061*
H15B	0.1348	0.3131	0.1117	0.061*
C16	0.4224 (6)	0.3412 (5)	0.07667 (11)	0.0719 (10)
H16A	0.4292	0.4547	0.0791	0.108*
H16B	0.3524	0.3117	0.0445	0.108*
H16C	0.5710	0.2984	0.0805	0.108*
C17	−0.0657 (5)	0.6828 (4)	0.17630 (10)	0.0423 (7)
C18	−0.0421 (5)	0.8569 (3)	0.16565 (10)	0.0409 (6)
C19	0.0338 (5)	0.8822 (4)	0.11393 (11)	0.0454 (7)
C20	−0.0995 (6)	0.9694 (5)	0.07920 (12)	0.0652 (9)
H20	−0.2368	1.0086	0.0873	0.078*
C21	−0.0247 (10)	0.9976 (7)	0.03192 (15)	0.0971 (15)
H21	−0.1105	1.0590	0.0088	0.117*
C22	0.1671 (11)	0.9375 (7)	0.01969 (16)	0.1064 (19)
H22	0.2118	0.9555	−0.0123	0.128*
C23	0.3032 (8)	0.8485 (7)	0.05326 (17)	0.0938 (16)
H23	0.4378	0.8073	0.0442	0.113*
C24	0.2338 (6)	0.8227 (4)	0.10066 (14)	0.0620 (9)
H24	0.3236	0.7642	0.1239	0.074*
H2	0.641 (4)	1.127 (4)	0.3229 (9)	0.038 (6)*
H4	1.258 (5)	0.191 (5)	0.3540 (12)	0.050 (9)*
H5	1.039 (8)	0.630 (7)	0.2900 (19)	0.11 (2)*
H6	1.242 (5)	0.590 (3)	0.3546 (9)	0.033 (7)*
H9A	−0.228 (6)	0.512 (6)	0.1554 (12)	0.056 (10)*
H10A	0.187 (7)	0.858 (6)	0.2133 (15)	0.073 (13)*
H13	0.956 (6)	0.988 (4)	0.2986 (11)	0.046 (8)*
H14	0.395 (4)	0.437 (4)	0.1733 (9)	0.038 (6)*
H15	0.777 (7)	1.005 (6)	0.2596 (16)	0.093 (14)*
H16	0.282 (7)	0.327 (6)	0.2384 (17)	0.106 (15)*
H17	0.075 (5)	0.297 (3)	0.2022 (10)	0.032 (7)*
H18	−0.189 (5)	0.899 (3)	0.1664 (10)	0.032 (7)*
H11A	0.503 (7)	0.587 (2)	0.2710 (14)	0.077 (13)*
H14A	0.796 (5)	0.869 (5)	0.2868 (11)	0.043 (9)*
H18A	0.219 (4)	0.176 (4)	0.2089 (10)	0.036 (8)*
H11B	0.644 (4)	0.483 (9)	0.2704 (18)	0.101 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0375 (10)	0.0409 (12)	0.0687 (13)	−0.0010 (9)	−0.0037 (9)	−0.0148 (10)
O2	0.0264 (10)	0.0567 (14)	0.0835 (15)	0.0046 (9)	0.0001 (10)	−0.0198 (12)
O3	0.0573 (13)	0.0576 (14)	0.0529 (12)	0.0006 (12)	−0.0120 (10)	−0.0032 (11)
O4	0.0562 (13)	0.0424 (13)	0.0583 (13)	0.0119 (10)	−0.0128 (10)	−0.0060 (10)
O5	0.103 (2)	0.0573 (15)	0.0569 (14)	0.0343 (15)	0.0271 (15)	0.0191 (12)
O6	0.0423 (11)	0.0380 (11)	0.0595 (12)	0.0063 (9)	0.0006 (9)	0.0122 (10)
O7	0.0284 (10)	0.0487 (12)	0.0664 (12)	−0.0043 (9)	0.0006 (9)	0.0078 (10)
O8	0.0649 (14)	0.0437 (12)	0.0560 (12)	0.0004 (11)	−0.0198 (10)	0.0048 (10)
O9	0.0541 (14)	0.0461 (15)	0.0764 (15)	−0.0112 (11)	−0.0218 (11)	0.0114 (12)
O10	0.0673 (15)	0.0403 (13)	0.0490 (12)	−0.0032 (11)	−0.0168 (11)	−0.0056 (10)
O11	0.0709 (17)	0.0620 (16)	0.0658 (15)	−0.0118 (15)	−0.0067 (13)	−0.0091 (13)
N1	0.0297 (12)	0.0415 (15)	0.0436 (14)	−0.0008 (11)	−0.0003 (10)	0.0012 (11)
N2	0.0314 (14)	0.0393 (15)	0.0473 (14)	0.0029 (11)	0.0017 (10)	0.0058 (11)
C1	0.0277 (12)	0.0305 (14)	0.0441 (14)	0.0025 (11)	−0.0012 (10)	0.0026 (12)
C2	0.0311 (13)	0.0328 (15)	0.0323 (13)	0.0001 (10)	−0.0019 (10)	0.0012 (10)
C3	0.0553 (18)	0.067 (2)	0.0390 (15)	0.0070 (17)	−0.0084 (13)	0.0012 (15)
C4	0.092 (3)	0.078 (3)	0.0497 (18)	0.011 (2)	0.0042 (18)	0.0004 (18)
C5	0.0348 (15)	0.0513 (17)	0.0400 (14)	0.0047 (13)	0.0023 (12)	0.0029 (13)
C6	0.0435 (17)	0.0423 (16)	0.0545 (17)	0.0014 (14)	0.0081 (13)	0.0041 (14)
C7	0.0450 (16)	0.0382 (14)	0.0458 (15)	0.0062 (13)	−0.0020 (12)	0.0015 (12)
C8	0.061 (2)	0.058 (2)	0.065 (2)	0.0045 (17)	−0.0117 (17)	−0.0079 (17)
C9	0.104 (3)	0.080 (3)	0.050 (2)	0.010 (3)	−0.015 (2)	−0.0130 (19)
C10	0.132 (4)	0.088 (3)	0.046 (2)	0.029 (3)	0.022 (2)	0.003 (2)
C11	0.077 (2)	0.076 (3)	0.069 (2)	0.010 (2)	0.027 (2)	0.016 (2)
C12	0.0514 (17)	0.0531 (19)	0.0498 (17)	0.0064 (15)	0.0063 (14)	0.0015 (14)
C13	0.0315 (13)	0.0308 (13)	0.0341 (12)	0.0002 (11)	−0.0001 (10)	−0.0026 (11)
C14	0.0305 (13)	0.0325 (14)	0.0322 (12)	−0.0007 (11)	0.0005 (10)	0.0033 (10)
C15	0.0456 (16)	0.066 (2)	0.0377 (14)	−0.0041 (15)	−0.0134 (12)	0.0013 (14)
C16	0.086 (2)	0.086 (3)	0.0422 (17)	−0.008 (2)	−0.0039 (16)	0.0104 (19)
C17	0.0361 (15)	0.0477 (17)	0.0424 (15)	−0.0004 (13)	−0.0010 (13)	−0.0016 (13)
C18	0.0355 (15)	0.0415 (16)	0.0447 (15)	0.0055 (12)	−0.0038 (12)	−0.0032 (13)
C19	0.0516 (17)	0.0373 (15)	0.0456 (15)	−0.0104 (13)	−0.0060 (13)	−0.0028 (12)
C20	0.077 (2)	0.060 (2)	0.0542 (18)	−0.0138 (19)	−0.0213 (16)	0.0042 (17)
C21	0.147 (4)	0.092 (4)	0.047 (2)	−0.028 (4)	−0.021 (2)	0.006 (2)
C22	0.164 (5)	0.105 (4)	0.053 (2)	−0.042 (4)	0.023 (3)	−0.011 (3)
C23	0.101 (3)	0.096 (4)	0.090 (3)	−0.025 (3)	0.045 (3)	−0.031 (3)
C24	0.064 (2)	0.057 (2)	0.066 (2)	−0.0047 (18)	0.0122 (17)	−0.0067 (17)

Geometric parameters (Å, º)

O1—C1	1.233 (3)	C6—H6	0.97 (3)
O2—C1	1.247 (3)	C7—C12	1.366 (4)
O3—C5	1.210 (4)	C7—C8	1.389 (4)
O4—C5	1.313 (4)	C8—C9	1.378 (5)
O4—H4	0.92 (4)	C8—H8	0.9300
O5—C6	1.424 (4)	C9—C10	1.342 (7)
O5—H5	0.79 (5)	C9—H9	0.9300
O6—C13	1.221 (3)	C10—C11	1.383 (6)
O7—C13	1.259 (3)	C10—H10	0.9300
O8—C17	1.227 (4)	C11—C12	1.390 (5)
O9—C17	1.294 (4)	C11—H11	0.9300
O9—H9A	0.87 (5)	C12—H12	0.9300
O10—C18	1.420 (4)	C13—C14	1.527 (4)
O10—H10A	0.81 (5)	C14—C15	1.522 (4)
O11—H11A	0.91 (2)	C14—H14	0.96 (3)
O11—H11B	0.86 (2)	C15—C16	1.512 (4)
N1—C2	1.479 (3)	C15—H15A	0.9700
N1—H13	0.88 (3)	C15—H15B	0.9700
N1—H15	0.91 (5)	C16—H16A	0.9600
N1—H14A	0.82 (4)	C16—H16B	0.9600
N2—C14	1.482 (3)	C16—H16C	0.9600
N2—H16	1.02 (5)	C17—C18	1.505 (4)
N2—H17	0.90 (3)	C18—C19	1.505 (4)
N2—H18A	0.79 (3)	C18—H18	0.95 (3)
C1—C2	1.528 (4)	C19—C24	1.373 (5)
C2—C3	1.536 (4)	C19—C20	1.387 (5)
C2—H2	0.93 (3)	C20—C21	1.395 (6)
C3—C4	1.493 (4)	C20—H20	0.9300
C3—H3A	0.9700	C21—C22	1.323 (7)
C3—H3B	0.9700	C21—H21	0.9300
C4—H4A	0.9600	C22—C23	1.385 (7)
C4—H4B	0.9600	C22—H22	0.9300
C4—H4C	0.9600	C23—C24	1.383 (6)
C5—C6	1.507 (4)	C23—H23	0.9300
C6—C7	1.514 (4)	C24—H24	0.9300
C5—O4—H4	114 (2)	C9—C10—H10	119.5
C6—O5—H5	103 (4)	C11—C10—H10	119.5
C17—O9—H9A	111 (2)	C10—C11—C12	118.9 (4)
C18—O10—H10A	104 (3)	C10—C11—H11	120.6
H11A—O11—H11B	88 (5)	C12—C11—H11	120.6
C2—N1—H13	116.3 (19)	C7—C12—C11	120.2 (3)
C2—N1—H15	110 (3)	C7—C12—H12	119.9
H13—N1—H15	108 (3)	C11—C12—H12	119.9
C2—N1—H14A	106 (2)	O6—C13—O7	126.1 (3)
H13—N1—H14A	112 (3)	O6—C13—C14	117.5 (2)
H15—N1—H14A	104 (4)	O7—C13—C14	116.3 (2)
C14—N2—H16	101 (3)	N2—C14—C15	109.0 (2)
C14—N2—H17	119.8 (17)	N2—C14—C13	107.8 (2)
H16—N2—H17	105 (3)	C15—C14—C13	112.4 (2)
C14—N2—H18A	112.4 (19)	N2—C14—H14	109.0 (14)
H16—N2—H18A	114 (3)	C15—C14—H14	112.1 (15)
H17—N2—H18A	104 (3)	C13—C14—H14	106.4 (15)
O1—C1—O2	126.1 (3)	C16—C15—C14	113.6 (3)
O1—C1—C2	118.1 (2)	C16—C15—H15A	108.8
O2—C1—C2	115.8 (2)	C14—C15—H15A	108.8
N1—C2—C1	108.7 (2)	C16—C15—H15B	108.8
N1—C2—C3	108.3 (2)	C14—C15—H15B	108.8
C1—C2—C3	112.3 (2)	H15A—C15—H15B	107.7
N1—C2—H2	107.3 (15)	C15—C16—H16A	109.5
C1—C2—H2	107.3 (16)	C15—C16—H16B	109.5
C3—C2—H2	112.8 (16)	H16A—C16—H16B	109.5
C4—C3—C2	114.9 (3)	C15—C16—H16C	109.5
C4—C3—H3A	108.5	H16A—C16—H16C	109.5
C2—C3—H3A	108.5	H16B—C16—H16C	109.5
C4—C3—H3B	108.5	O8—C17—O9	124.3 (3)
C2—C3—H3B	108.5	O8—C17—C18	121.5 (3)
H3A—C3—H3B	107.5	O9—C17—C18	114.2 (3)
C3—C4—H4A	109.5	O10—C18—C17	110.5 (2)
C3—C4—H4B	109.5	O10—C18—C19	111.3 (2)
H4A—C4—H4B	109.5	C17—C18—C19	110.6 (2)
C3—C4—H4C	109.5	O10—C18—H18	110.8 (17)
H4A—C4—H4C	109.5	C17—C18—H18	105.0 (17)
H4B—C4—H4C	109.5	C19—C18—H18	108.4 (16)
O3—C5—O4	123.6 (3)	C24—C19—C20	119.3 (3)
O3—C5—C6	123.2 (3)	C24—C19—C18	121.4 (3)
O4—C5—C6	113.2 (3)	C20—C19—C18	119.3 (3)
O5—C6—C5	109.2 (3)	C19—C20—C21	119.1 (4)
O5—C6—C7	107.9 (2)	C19—C20—H20	120.4
C5—C6—C7	111.8 (2)	C21—C20—H20	120.4
O5—C6—H6	109.3 (17)	C22—C21—C20	120.6 (5)
C5—C6—H6	108.7 (17)	C22—C21—H21	119.7
C7—C6—H6	109.9 (15)	C20—C21—H21	119.7
C12—C7—C8	119.8 (3)	C21—C22—C23	121.8 (4)
C12—C7—C6	120.7 (3)	C21—C22—H22	119.1
C8—C7—C6	119.4 (3)	C23—C22—H22	119.1
C9—C8—C7	119.5 (3)	C24—C23—C22	118.3 (4)
C9—C8—H8	120.3	C24—C23—H23	120.9
C7—C8—H8	120.3	C22—C23—H23	120.9
C10—C9—C8	120.7 (4)	C19—C24—C23	120.8 (4)
C10—C9—H9	119.7	C19—C24—H24	119.6
C8—C9—H9	119.7	C23—C24—H24	119.6
C9—C10—C11	121.0 (3)
O1—C1—C2—N1	25.1 (3)	O6—C13—C14—N2	26.1 (3)
O2—C1—C2—N1	−156.5 (2)	O7—C13—C14—N2	−156.8 (2)
O1—C1—C2—C3	−94.7 (3)	O6—C13—C14—C15	−94.0 (3)
O2—C1—C2—C3	83.7 (3)	O7—C13—C14—C15	83.1 (3)
N1—C2—C3—C4	175.1 (3)	N2—C14—C15—C16	174.1 (3)
C1—C2—C3—C4	−64.8 (4)	C13—C14—C15—C16	−66.5 (4)
O3—C5—C6—O5	−12.4 (4)	O8—C17—C18—O10	−10.9 (4)
O4—C5—C6—O5	168.3 (2)	O9—C17—C18—O10	169.1 (2)
O3—C5—C6—C7	106.9 (3)	O8—C17—C18—C19	112.8 (3)
O4—C5—C6—C7	−72.3 (3)	O9—C17—C18—C19	−67.2 (3)
O5—C6—C7—C12	69.8 (4)	O10—C18—C19—C24	62.7 (4)
C5—C6—C7—C12	−50.3 (4)	C17—C18—C19—C24	−60.5 (4)
O5—C6—C7—C8	−107.5 (3)	O10—C18—C19—C20	−116.3 (3)
C5—C6—C7—C8	132.3 (3)	C17—C18—C19—C20	120.5 (3)
C12—C7—C8—C9	−0.7 (5)	C24—C19—C20—C21	−1.4 (5)
C6—C7—C8—C9	176.7 (3)	C18—C19—C20—C21	177.7 (3)
C7—C8—C9—C10	0.8 (6)	C19—C20—C21—C22	2.3 (7)
C8—C9—C10—C11	−0.2 (7)	C20—C21—C22—C23	−1.6 (8)
C9—C10—C11—C12	−0.5 (6)	C21—C22—C23—C24	0.1 (7)
C8—C7—C12—C11	0.0 (5)	C20—C19—C24—C23	0.0 (5)
C6—C7—C12—C11	−177.4 (3)	C18—C19—C24—C23	−179.1 (3)
C10—C11—C12—C7	0.6 (5)	C22—C23—C24—C19	0.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O8	0.81 (5)	2.19 (5)	2.667 (3)	119 (4)
O10—H10A···O1	0.81 (5)	2.29 (4)	2.908 (3)	134 (4)
N2—H16···O11	1.02 (5)	2.03 (5)	2.959 (4)	150 (4)
O11—H11A···O1	0.91 (2)	2.10 (2)	2.962 (4)	159 (3)
N1—H14A···O5	0.82 (4)	2.30 (4)	2.962 (4)	139 (3)
O11—H11B···O3	0.86 (2)	2.52 (5)	3.194 (4)	136 (6)
O4—H4···O2^i	0.92 (4)	1.65 (4)	2.561 (3)	168 (3)
O5—H5···O8^ii	0.79 (5)	2.20 (5)	2.904 (3)	148 (5)
O9—H9A···O7^iii	0.87 (5)	1.63 (5)	2.505 (3)	177 (3)
N1—H13···O2^ii	0.88 (3)	1.91 (4)	2.786 (3)	172 (3)
N1—H15···O6^iv	0.91 (5)	1.93 (5)	2.787 (3)	158 (4)
N2—H17···O7^iii	0.90 (3)	1.95 (3)	2.820 (3)	161 (2)
N2—H18A···O10^v	0.79 (3)	2.19 (3)	2.953 (4)	161 (3)

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