L-Asparaginyl-L-valine 1.33-hydrate

The title compound, C₉H₁₇N₃O₄·1.33H₂O, crystallizes with three peptide mol­ecules and four water mol­ecules in the asymmetric unit. Two of the peptide mol­ecules contain an intramolecular hydrogen bond between the N-terminal amino group and the asparagine side chain. Valine side chains aggregate into large hydro­phobic columns.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.032
• wR factor = 0.086
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.33 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.06 Ratio

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:   C9 H19.67 N3 O5.33
            Atom count from _chemical_formula_moiety:C9 H19.66 N3 O5.33
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z   12
           From the CIF: _chemical_formula_sum  C9 H19.67 N3 O5.33
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        108.00    108.00    0.00
           H        236.04    236.00    0.04
           N         36.00     36.00    0.00
           O         63.96     64.00   -0.04
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           37.37
           From the CIF: _reflns_number_total              10215
           Count of symmetry unique reflns        10593
           Completeness (_total/calc)             96.43%
           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
   5 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

L-Asparaginyl-L-valine

Crystal data

C9H17N3O4·1.33H2O	Dx = 1.367 Mg m^−3
Mr = 255.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7607 reflections
a = 9.0002 (5) Å	θ = 2.6–37,08°
b = 15.0542 (7) Å	µ = 0.11 mm^−1
c = 27.4541 (14) Å	T = 105 K
V = 3719.8 (3) Å^3	Plate, colourless
Z = 12	0.60 × 0.45 × 0.10 mm
F(000) = 1648

Data collection

Siemens SMART CCD diffractometer	10215 independent reflections
Radiation source: fine-focus sealed tube	9027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.3 pixels mm^-1	θmax = 37.4°, θmin = 1.5°
Sets of exposures each taken over 0.3° ω rotation scans	h = −14→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −25→22
Tmin = 0.848, Tmax = 0.989	l = −45→46
56666 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.1965P] where P = (Fo^2 + 2Fc^2)/3
10215 reflections	(Δ/σ)max = 0.004
547 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.23 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. Data were collected by measuring two sets of exposures with the detector set at 2θ = 29° and three sets of exposures with the detector set at 2θ = 48°, crystal-to-detector distance 5.08 cm. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq
O1A	0.20605 (9)	0.86687 (5)	0.01907 (3)	0.01967 (14)
O2A	0.41840 (9)	0.63462 (5)	0.13275 (3)	0.01851 (13)
O3A	0.48184 (11)	0.80449 (6)	−0.06192 (3)	0.02634 (17)
O4A	0.48586 (11)	0.92153 (6)	−0.11194 (3)	0.02686 (18)
N1A	0.22529 (9)	0.77860 (5)	0.10537 (3)	0.01458 (13)
H1A	0.187 (2)	0.8346 (11)	0.1200 (6)	0.022*
H2A	0.2455 (19)	0.7375 (12)	0.1268 (6)	0.022*
H3A	0.148 (2)	0.7556 (11)	0.0876 (6)	0.022*
N2A	0.45308 (10)	0.90221 (6)	0.01887 (3)	0.01581 (14)
H4A	0.5360 (19)	0.8835 (11)	0.0286 (6)	0.019*
N3A	0.60315 (11)	0.60031 (6)	0.07974 (3)	0.01925 (15)
H5A	0.640 (2)	0.5624 (11)	0.1000 (6)	0.023*
H6A	0.641 (2)	0.6001 (11)	0.0509 (6)	0.023*
C1A	0.36447 (10)	0.79485 (6)	0.07714 (3)	0.01322 (14)
H11A	0.4422	0.8204	0.0991	0.016*
C2A	0.42139 (11)	0.70817 (6)	0.05464 (3)	0.01555 (15)
H21A	0.3392	0.6790	0.0368	0.019*
H22A	0.5008	0.7220	0.0309	0.019*
C3A	0.48159 (10)	0.64469 (6)	0.09251 (3)	0.01397 (14)
C4A	0.33281 (10)	0.85941 (6)	0.03557 (3)	0.01349 (14)
C5A	0.44889 (11)	0.95015 (6)	−0.02731 (3)	0.01416 (14)
H51A	0.3463	0.9748	−0.0309	0.017*
C6A	0.55674 (12)	1.02957 (6)	−0.02741 (4)	0.01796 (16)
H61A	0.5422	1.0616	−0.0590	0.022*
C7A	0.71931 (13)	1.00044 (9)	−0.02547 (6)	0.0300 (2)
H71A	0.7836	1.0530	−0.0256	0.045*
H72A	0.7419	0.9635	−0.0539	0.045*
H73A	0.7367	0.9661	0.0043	0.045*
C8A	0.5184 (2)	1.09468 (8)	0.01326 (5)	0.0328 (3)
H81A	0.5883	1.1446	0.0126	0.049*
H82A	0.5251	1.0644	0.0448	0.049*
H83A	0.4171	1.1169	0.0085	0.049*
C9A	0.47505 (11)	0.88644 (7)	−0.07081 (4)	0.01690 (16)
O1B	0.24073 (9)	0.34341 (5)	0.18445 (3)	0.01856 (13)
O2B	0.11457 (10)	0.67532 (5)	0.21363 (3)	0.02438 (16)
O3B	0.70727 (9)	0.49434 (5)	0.15813 (3)	0.02214 (15)
O4B	0.75514 (9)	0.36333 (5)	0.19347 (3)	0.02301 (15)
N1B	0.02838 (9)	0.46899 (6)	0.19062 (3)	0.01638 (14)
H1B	−0.029 (2)	0.4989 (12)	0.2085 (6)	0.025*
H2B	0.026 (2)	0.4101 (12)	0.2005 (6)	0.025*
H3B	−0.010 (2)	0.4746 (12)	0.1630 (7)	0.025*
N2B	0.41348 (9)	0.44196 (5)	0.15635 (3)	0.01482 (13)
H4B	0.4347 (19)	0.4988 (11)	0.1512 (6)	0.018*
N3B	0.23120 (12)	0.67291 (6)	0.28678 (4)	0.02164 (17)
H5B	0.220 (2)	0.7282 (12)	0.2896 (6)	0.026*
H6B	0.293 (2)	0.6437 (12)	0.3073 (6)	0.026*
C1B	0.18555 (10)	0.49966 (6)	0.18975 (3)	0.01310 (14)
H11B	0.1965	0.5466	0.1642	0.016*
C2B	0.23224 (11)	0.53826 (6)	0.23906 (4)	0.01698 (16)
H21B	0.1869	0.5024	0.2654	0.020*
H22B	0.3415	0.5336	0.2423	0.020*
C3B	0.18639 (11)	0.63527 (6)	0.24553 (4)	0.01652 (15)
C4B	0.28313 (10)	0.42014 (6)	0.17614 (3)	0.01285 (14)
C5B	0.53223 (10)	0.37808 (6)	0.14644 (3)	0.01385 (14)
H51B	0.5074	0.3208	0.1630	0.017*
C6B	0.54775 (11)	0.36069 (6)	0.09112 (4)	0.01650 (15)
H61B	0.5463	0.4190	0.0737	0.020*
C7B	0.41705 (13)	0.30523 (8)	0.07337 (4)	0.0244 (2)
H71B	0.4273	0.2943	0.0383	0.037*
H72B	0.3242	0.3373	0.0796	0.037*
H73B	0.4156	0.2484	0.0908	0.037*
C8B	0.69364 (14)	0.31356 (9)	0.07934 (5)	0.0272 (2)
H81B	0.7003	0.3035	0.0441	0.041*
H82B	0.6970	0.2564	0.0964	0.041*
H83B	0.7772	0.3506	0.0899	0.041*
C9B	0.67723 (11)	0.41449 (6)	0.16838 (3)	0.01523 (15)
O1C	0.85856 (10)	0.55493 (5)	0.25862 (3)	0.02169 (15)
O2C	0.62703 (9)	0.81020 (5)	0.16753 (3)	0.02171 (15)
O3C	0.88908 (9)	0.43339 (5)	0.35735 (3)	0.01967 (14)
O4C	0.66267 (9)	0.49098 (6)	0.34853 (3)	0.02330 (15)
N1C	0.80173 (11)	0.66366 (6)	0.18521 (3)	0.01710 (14)
H1C	0.901 (2)	0.6644 (12)	0.1824 (6)	0.026*
H2C	0.762 (2)	0.7002 (12)	0.1622 (6)	0.026*
H3C	0.767 (2)	0.6061 (12)	0.1791 (6)	0.026*
N2C	0.80351 (10)	0.65055 (5)	0.31861 (3)	0.01441 (13)
H4C	0.7770 (18)	0.7050 (11)	0.3252 (6)	0.017*
N3C	0.43139 (12)	0.84194 (7)	0.21582 (4)	0.02318 (18)
H5C	0.402 (2)	0.8890 (13)	0.1966 (7)	0.028*
H6C	0.383 (2)	0.8317 (12)	0.2427 (7)	0.028*
C1C	0.75604 (10)	0.69601 (6)	0.23445 (3)	0.01333 (14)
H11C	0.8082	0.7534	0.2410	0.016*
C2C	0.58786 (11)	0.71316 (6)	0.23535 (3)	0.01550 (15)
H21C	0.5347	0.6602	0.2230	0.019*
H22C	0.5552	0.7240	0.2693	0.019*
C3C	0.54970 (11)	0.79334 (6)	0.20388 (3)	0.01633 (15)
C4C	0.80927 (11)	0.62767 (6)	0.27167 (3)	0.01390 (14)
C5C	0.87204 (10)	0.59099 (6)	0.35438 (3)	0.01304 (14)
H51C	0.9792	0.5841	0.3455	0.016*
C6C	0.86471 (12)	0.63202 (6)	0.40562 (3)	0.01675 (15)
H61C	0.7585	0.6451	0.4135	0.020*
C7C	0.95227 (16)	0.71887 (8)	0.40709 (5)	0.0277 (2)
H71C	0.9466	0.7444	0.4399	0.042*
H72C	0.9100	0.7608	0.3836	0.042*
H73C	1.0563	0.7072	0.3988	0.042*
C8C	0.92597 (18)	0.56847 (8)	0.44409 (4)	0.0301 (3)
H81C	0.9198	0.5964	0.4763	0.045*
H82C	1.0299	0.5546	0.4366	0.045*
H83C	0.8675	0.5136	0.4440	0.045*
C9C	0.79984 (11)	0.49841 (6)	0.35276 (3)	0.01500 (14)
O1W	0.80568 (12)	0.94473 (7)	0.12903 (4)	0.03211 (19)
H11W	0.773 (3)	0.9074 (16)	0.1481 (9)	0.048*
H12W	0.903 (3)	0.9389 (16)	0.1325 (9)	0.048*
O2W	0.73859 (11)	0.82052 (7)	0.05377 (4)	0.03002 (19)
H21W	0.805 (3)	0.7785 (15)	0.0557 (8)	0.045*
H22W	0.767 (3)	0.8605 (15)	0.0742 (8)	0.045*
O3W	0.99476 (10)	0.84862 (6)	0.22459 (3)	0.02417 (15)
H31W	1.052 (2)	0.7965 (14)	0.2216 (7)	0.036*
H32W	1.034 (2)	0.8827 (14)	0.2008 (8)	0.036*
O4W	0.59835 (14)	1.08551 (8)	0.14330 (4)	0.0368 (2)
H41W	0.523 (3)	1.0635 (17)	0.1480 (9)	0.055*
H42W	0.658 (3)	1.0419 (17)	0.1313 (9)	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0164 (3)	0.0224 (3)	0.0202 (3)	−0.0001 (3)	−0.0024 (3)	0.0068 (3)
O2A	0.0236 (3)	0.0161 (3)	0.0159 (3)	0.0025 (3)	0.0044 (3)	0.0041 (2)
O3A	0.0314 (4)	0.0156 (3)	0.0320 (4)	0.0015 (3)	0.0096 (3)	−0.0034 (3)
O4A	0.0351 (5)	0.0310 (4)	0.0145 (3)	−0.0045 (4)	0.0002 (3)	0.0004 (3)
N1A	0.0168 (3)	0.0121 (3)	0.0149 (3)	0.0002 (3)	0.0016 (3)	0.0010 (2)
N2A	0.0161 (3)	0.0162 (3)	0.0151 (3)	−0.0013 (3)	−0.0009 (3)	0.0040 (3)
N3A	0.0196 (4)	0.0192 (4)	0.0190 (3)	0.0062 (3)	0.0039 (3)	0.0066 (3)
C1A	0.0155 (3)	0.0114 (3)	0.0127 (3)	0.0005 (3)	−0.0005 (3)	0.0013 (3)
C2A	0.0199 (4)	0.0135 (3)	0.0133 (3)	0.0031 (3)	0.0001 (3)	0.0014 (3)
C3A	0.0157 (3)	0.0109 (3)	0.0153 (3)	−0.0001 (3)	0.0001 (3)	0.0016 (3)
C4A	0.0172 (4)	0.0107 (3)	0.0125 (3)	0.0002 (3)	0.0002 (3)	0.0005 (3)
C5A	0.0167 (3)	0.0127 (3)	0.0131 (3)	0.0004 (3)	0.0004 (3)	0.0023 (3)
C6A	0.0232 (4)	0.0125 (3)	0.0182 (4)	−0.0023 (3)	−0.0005 (3)	0.0019 (3)
C7A	0.0211 (5)	0.0261 (5)	0.0428 (6)	−0.0067 (4)	−0.0033 (5)	0.0086 (5)
C8A	0.0540 (8)	0.0185 (5)	0.0260 (5)	−0.0039 (5)	0.0015 (5)	−0.0055 (4)
C9A	0.0154 (4)	0.0177 (4)	0.0176 (4)	−0.0015 (3)	0.0008 (3)	−0.0020 (3)
O1B	0.0194 (3)	0.0096 (3)	0.0267 (3)	−0.0011 (2)	0.0072 (3)	0.0001 (2)
O2B	0.0282 (4)	0.0141 (3)	0.0308 (4)	0.0047 (3)	−0.0076 (3)	−0.0034 (3)
O3B	0.0223 (3)	0.0138 (3)	0.0303 (4)	−0.0048 (3)	−0.0084 (3)	0.0072 (3)
O4B	0.0221 (3)	0.0168 (3)	0.0301 (4)	0.0003 (3)	−0.0073 (3)	0.0082 (3)
N1B	0.0134 (3)	0.0151 (3)	0.0206 (4)	−0.0001 (3)	0.0017 (3)	−0.0036 (3)
N2B	0.0136 (3)	0.0092 (3)	0.0216 (3)	0.0005 (2)	0.0039 (3)	0.0006 (3)
N3B	0.0261 (4)	0.0147 (3)	0.0241 (4)	0.0009 (3)	−0.0024 (3)	−0.0070 (3)
C1B	0.0124 (3)	0.0101 (3)	0.0169 (3)	0.0000 (3)	0.0013 (3)	−0.0008 (3)
C2B	0.0186 (4)	0.0121 (3)	0.0202 (4)	0.0022 (3)	−0.0032 (3)	−0.0031 (3)
C3B	0.0152 (3)	0.0116 (3)	0.0227 (4)	−0.0004 (3)	0.0014 (3)	−0.0038 (3)
C4B	0.0133 (3)	0.0099 (3)	0.0153 (3)	0.0007 (3)	0.0017 (3)	−0.0005 (3)
C5B	0.0124 (3)	0.0104 (3)	0.0188 (3)	0.0006 (3)	0.0017 (3)	0.0011 (3)
C6B	0.0160 (3)	0.0142 (4)	0.0194 (4)	0.0006 (3)	0.0022 (3)	−0.0011 (3)
C7B	0.0232 (5)	0.0223 (5)	0.0279 (5)	−0.0039 (4)	−0.0009 (4)	−0.0058 (4)
C8B	0.0215 (5)	0.0292 (5)	0.0308 (5)	0.0063 (4)	0.0057 (4)	−0.0058 (4)
C9B	0.0147 (3)	0.0131 (3)	0.0180 (4)	−0.0002 (3)	−0.0003 (3)	0.0034 (3)
O1C	0.0338 (4)	0.0144 (3)	0.0169 (3)	0.0094 (3)	0.0043 (3)	0.0000 (2)
O2C	0.0217 (3)	0.0219 (3)	0.0214 (3)	0.0035 (3)	0.0025 (3)	0.0083 (3)
O3C	0.0262 (4)	0.0111 (3)	0.0217 (3)	0.0023 (3)	0.0005 (3)	0.0016 (2)
O4C	0.0181 (3)	0.0188 (3)	0.0330 (4)	−0.0047 (3)	−0.0003 (3)	−0.0025 (3)
N1C	0.0225 (4)	0.0141 (3)	0.0147 (3)	0.0025 (3)	0.0031 (3)	0.0013 (3)
N2C	0.0197 (3)	0.0094 (3)	0.0142 (3)	0.0029 (3)	−0.0013 (3)	−0.0007 (2)
N3C	0.0237 (4)	0.0229 (4)	0.0229 (4)	0.0091 (3)	0.0024 (3)	0.0049 (3)
C1C	0.0158 (3)	0.0107 (3)	0.0134 (3)	0.0012 (3)	0.0006 (3)	0.0002 (3)
C2C	0.0156 (3)	0.0148 (4)	0.0161 (3)	0.0011 (3)	0.0004 (3)	0.0027 (3)
C3C	0.0170 (4)	0.0151 (4)	0.0169 (3)	0.0013 (3)	−0.0023 (3)	0.0013 (3)
C4C	0.0155 (3)	0.0118 (3)	0.0144 (3)	0.0011 (3)	0.0012 (3)	0.0004 (3)
C5C	0.0150 (3)	0.0100 (3)	0.0142 (3)	0.0004 (3)	−0.0008 (3)	0.0005 (3)
C6C	0.0214 (4)	0.0136 (3)	0.0152 (3)	0.0002 (3)	−0.0029 (3)	−0.0025 (3)
C7C	0.0339 (6)	0.0179 (4)	0.0312 (5)	−0.0061 (4)	−0.0095 (5)	−0.0057 (4)
C8C	0.0505 (8)	0.0229 (5)	0.0171 (4)	0.0050 (5)	−0.0091 (5)	0.0000 (4)
C9C	0.0193 (4)	0.0114 (3)	0.0144 (3)	−0.0014 (3)	0.0004 (3)	−0.0008 (3)
O1W	0.0283 (4)	0.0291 (4)	0.0389 (5)	−0.0084 (4)	0.0021 (4)	0.0037 (4)
O2W	0.0283 (4)	0.0318 (5)	0.0300 (4)	0.0048 (4)	−0.0052 (4)	−0.0049 (4)
O3W	0.0250 (4)	0.0191 (3)	0.0284 (4)	−0.0022 (3)	0.0052 (3)	0.0014 (3)
O4W	0.0337 (5)	0.0357 (5)	0.0411 (5)	−0.0088 (4)	−0.0066 (4)	−0.0015 (4)

Geometric parameters (Å, º)

O1A—C4A	1.2327 (12)	C5B—C9B	1.5382 (13)
O2A—C3A	1.2517 (11)	C5B—C6B	1.5476 (14)
O3A—C9A	1.2590 (13)	C5B—H51B	1.0000
O4A—C9A	1.2503 (13)	C6B—C7B	1.5226 (15)
N1A—C1A	1.4932 (12)	C6B—C8B	1.5271 (15)
N1A—H1A	0.997 (17)	C6B—H61B	1.0000
N1A—H2A	0.873 (18)	C7B—H71B	0.9800
N1A—H3A	0.916 (18)	C7B—H72B	0.9800
N2A—C4A	1.3406 (12)	C7B—H73B	0.9800
N2A—C5A	1.4593 (12)	C8B—H81B	0.9800
N2A—H4A	0.841 (17)	C8B—H82B	0.9800
N3A—C3A	1.3291 (13)	C8B—H82B	0.9800
N3A—H5A	0.865 (18)	O1C—C4C	1.2347 (11)
N3A—H6A	0.863 (17)	O2C—C3C	1.2429 (13)
C1A—C4A	1.5258 (12)	O3C—C9C	1.2723 (12)
C1A—C2A	1.5320 (13)	O4C—C9C	1.2450 (13)
C1A—H11A	1.0000	N1C—C1C	1.4946 (12)
C2A—C3A	1.5127 (13)	N1C—H1C	0.896 (19)
C2A—H21A	0.9900	N1C—H2C	0.909 (18)
C2A—H22A	0.9900	N1C—H3C	0.936 (18)
C5A—C6A	1.5400 (13)	N2C—C4C	1.3348 (12)
C5A—C9A	1.5498 (13)	N2C—C5C	1.4659 (12)
C5A—H51A	1.0000	N2C—H4C	0.873 (16)
C6A—C8A	1.5254 (16)	N3C—C3C	1.3328 (14)
C6A—C7A	1.5284 (17)	N3C—H5C	0.923 (19)
C6A—H61A	1.0000	N3C—H6C	0.873 (19)
C7A—H71A	0.9800	C1C—C4C	1.5271 (13)
C7A—H72A	0.9800	C1C—C2C	1.5357 (14)
C7A—H73A	0.9800	C1C—H11C	1.0000
C8A—H81A	0.9800	C2C—C3C	1.5237 (13)
C8A—H82A	0.9800	C2C—H21C	0.9900
C8A—H83A	0.9800	C2C—H22C	0.9900
O1B—C4B	1.2377 (11)	C5C—C6C	1.5378 (13)
O2B—C3B	1.2444 (13)	C5C—C9C	1.5384 (13)
O3B—C9B	1.2639 (12)	C5C—H51C	1.0000
O4B—C9B	1.2488 (12)	C6C—C7C	1.5271 (15)
N1B—C1B	1.4883 (12)	C6C—C8C	1.5281 (15)
N1B—H1B	0.842 (18)	C6C—H61C	1.0000
N1B—H2B	0.927 (18)	C7C—H71C	0.9800
N1B—H3B	0.839 (18)	C7C—H72C	0.9800
N2B—C4B	1.3340 (12)	C7C—H73C	0.9800
N2B—C5B	1.4632 (12)	C8C—H81C	0.9800
N2B—H4B	0.887 (17)	C8C—H82C	0.9800
N3B—C3B	1.3290 (13)	C8C—H83C	0.9800
N3B—H5B	0.842 (18)	O1W—H11W	0.82 (2)
N3B—H6B	0.905 (19)	O1W—H12W	0.88 (3)
C1B—C4B	1.5310 (12)	O2W—H21W	0.87 (2)
C1B—C2B	1.5321 (13)	O2W—H22W	0.86 (2)
C1B—H11B	1.0000	O3W—H31W	0.94 (2)
C2B—C3B	1.5280 (13)	O3W—H32W	0.90 (2)
C2B—H21B	0.9900	O4W—H41W	0.77 (3)
C2B—H22B	0.9900	O4W—H42W	0.91 (3)
C1A—N1A—H1A	111.3 (10)	N2B—C5B—C9B	108.23 (7)
C1A—N1A—H2A	106.9 (12)	N2B—C5B—C6B	111.07 (8)
H1A—N1A—H2A	113.6 (14)	C9B—C5B—C6B	111.58 (8)
C1A—N1A—H3A	114.8 (10)	N2B—C5B—H51B	108.6
H1A—N1A—H3A	105.7 (15)	C9B—C5B—H51B	108.6
H2A—N1A—H3A	104.5 (15)	C6B—C5B—H51B	108.6
C4A—N2A—C5A	120.94 (8)	C7B—C6B—C8B	109.98 (9)
C4A—N2A—H4A	116.6 (11)	C7B—C6B—C5B	109.71 (8)
C5A—N2A—H4A	117.6 (11)	C8B—C6B—C5B	111.36 (9)
C3A—N3A—H5A	118.7 (12)	C7B—C6B—H61B	108.6
C3A—N3A—H6A	125.0 (12)	C8B—C6B—H61B	108.6
H5A—N3A—H6A	115.7 (17)	C5B—C6B—H61B	108.6
N1A—C1A—C4A	109.63 (7)	C6B—C7B—H71B	109.5
N1A—C1A—C2A	110.51 (7)	C6B—C7B—H72B	109.5
C4A—C1A—C2A	107.66 (7)	H71B—C7B—H72B	109.5
N1A—C1A—H11A	109.7	C6B—C7B—H73B	109.5
C4A—C1A—H11A	109.7	H71B—C7B—H73B	109.5
C2A—C1A—H11A	109.7	H72B—C7B—H73B	109.5
C3A—C2A—C1A	112.37 (7)	C6B—C8B—H81B	109.5
C3A—C2A—H21A	109.1	C6B—C8B—H82B	109.5
C1A—C2A—H21A	109.1	H81B—C8B—H82B	109.5
C3A—C2A—H22A	109.1	C6B—C8B—H82B	109.5
C1A—C2A—H22A	109.1	H81B—C8B—H82B	109.5
H21A—C2A—H22A	107.9	H82B—C8B—H82B	109.5
O2A—C3A—N3A	123.10 (9)	O4B—C9B—O3B	126.11 (10)
O2A—C3A—C2A	121.37 (8)	O4B—C9B—C5B	118.20 (8)
N3A—C3A—C2A	115.53 (8)	O3B—C9B—C5B	115.67 (8)
O1A—C4A—N2A	125.29 (8)	C1C—N1C—H1C	110.4 (11)
O1A—C4A—C1A	120.39 (8)	C1C—N1C—H2C	108.8 (11)
N2A—C4A—C1A	114.28 (8)	H1C—N1C—H2C	108.8 (17)
N2A—C5A—C6A	111.67 (8)	C1C—N1C—H3C	111.8 (11)
N2A—C5A—C9A	111.06 (8)	H1C—N1C—H3C	109.3 (17)
C6A—C5A—C9A	112.54 (8)	H2C—N1C—H3C	107.7 (16)
N2A—C5A—H51A	107.1	C4C—N2C—C5C	118.19 (7)
C6A—C5A—H51A	107.1	C4C—N2C—H4C	116.9 (10)
C9A—C5A—H51A	107.1	C5C—N2C—H4C	123.5 (10)
C8A—C6A—C7A	112.06 (11)	C3C—N3C—H5C	120.8 (12)
C8A—C6A—C5A	110.78 (9)	C3C—N3C—H6C	120.9 (12)
C7A—C6A—C5A	112.37 (8)	H5C—N3C—H6C	118.3 (17)
C8A—C6A—H61A	107.1	N1C—C1C—C4C	107.42 (7)
C7A—C6A—H61A	107.1	N1C—C1C—C2C	109.91 (8)
C5A—C6A—H61A	107.1	C4C—C1C—C2C	114.31 (8)
C6A—C7A—H71A	109.5	N1C—C1C—H11C	108.3
C6A—C7A—H72A	109.5	C4C—C1C—H11C	108.3
H71A—C7A—H72A	109.5	C2C—C1C—H11C	108.3
C6A—C7A—H73A	109.5	C3C—C2C—C1C	110.26 (8)
H71A—C7A—H73A	109.5	C3C—C2C—H21C	109.6
H72A—C7A—H73A	109.5	C1C—C2C—H21C	109.6
C6A—C8A—H81A	109.5	C3C—C2C—H22C	109.6
C6A—C8A—H82A	109.5	C1C—C2C—H22C	109.6
H81A—C8A—H82A	109.5	O2C—C3C—N3C	122.19 (9)
C6A—C8A—H83A	109.5	O2C—C3C—C2C	119.39 (9)
H81A—C8A—H83A	109.5	N3C—C3C—C2C	118.39 (9)
H82A—C8A—H83A	109.5	O1C—C4C—N2C	121.54 (8)
O4A—C9A—O3A	125.82 (10)	O1C—C4C—C1C	121.07 (8)
O4A—C9A—C5A	116.50 (9)	N2C—C4C—C1C	117.38 (8)
O3A—C9A—C5A	117.67 (9)	N2C—C5C—C6C	110.43 (7)
C1B—N1B—H1B	115.1 (12)	N2C—C5C—C9C	110.92 (7)
C1B—N1B—H2B	109.0 (12)	C6C—C5C—C9C	111.85 (7)
H1B—N1B—H2B	109.0 (17)	N2C—C5C—H51C	107.8
C1B—N1B—H3B	110.5 (12)	C6C—C5C—H51C	107.8
H1B—N1B—H3B	102.5 (17)	C9C—C5C—H51C	107.8
H2B—N1B—H3B	110.6 (17)	C7C—C6C—C8C	109.36 (9)
C4B—N2B—C5B	123.80 (8)	C7C—C6C—C5C	110.25 (9)
C4B—N2B—H4B	119.4 (11)	C8C—C6C—C5C	111.43 (8)
C5B—N2B—H4B	116.5 (11)	C7C—C6C—H61C	108.6
C3B—N3B—H5B	117.5 (12)	C8C—C6C—H61C	108.6
C3B—N3B—H6B	120.6 (11)	C5C—C6C—H61C	108.6
H5B—N3B—H6B	120.0 (17)	C6C—C7C—H71C	109.5
N1B—C1B—C4B	107.85 (7)	C6C—C7C—H72C	109.5
N1B—C1B—C2B	111.35 (8)	H71C—C7C—H72C	109.5
C4B—C1B—C2B	110.78 (7)	C6C—C7C—H73C	109.5
N1B—C1B—H11B	108.9	H71C—C7C—H73C	109.5
C4B—C1B—H11B	108.9	H72C—C7C—H73C	109.5
C2B—C1B—H11B	108.9	C6C—C8C—H81C	109.5
C3B—C2B—C1B	113.03 (8)	C6C—C8C—H82C	109.5
C3B—C2B—H21B	109.0	H81C—C8C—H82C	109.5
C1B—C2B—H21B	109.0	C6C—C8C—H83C	109.5
C3B—C2B—H22B	109.0	H81C—C8C—H83C	109.5
C1B—C2B—H22B	109.0	H82C—C8C—H83C	109.5
H21B—C2B—H22B	107.8	O4C—C9C—O3C	124.48 (9)
O2B—C3B—N3B	123.42 (9)	O4C—C9C—C5C	120.19 (9)
O2B—C3B—C2B	121.43 (9)	O3C—C9C—C5C	115.30 (8)
N3B—C3B—C2B	115.13 (9)	H11W—O1W—H12W	102 (2)
O1B—C4B—N2B	125.16 (8)	H21W—O2W—H22W	105 (2)
O1B—C4B—C1B	120.53 (8)	H31W—O3W—H32W	101.4 (18)
N2B—C4B—C1B	114.29 (8)	H41W—O4W—H42W	106 (2)
N1A—C1A—C4A—N2A	157.91 (8)	C5B—N2B—C4B—O1B	−6.95 (15)
C1A—C4A—N2A—C5A	165.88 (8)	N1B—C1B—C4B—O1B	−25.29 (12)
C4A—N2A—C5A—C9A	−83.12 (11)	C2B—C1B—C4B—O1B	96.81 (10)
N2A—C5A—C9A—O3A	6.45 (13)	C2B—C1B—C4B—N2B	−81.87 (10)
N1A—C1A—C2A—C3A	−70.21 (10)	C4B—N2B—C5B—C6B	107.84 (10)
C1A—C2A—C3A—O2A	40.23 (13)	C9B—C5B—C6B—C7B	166.74 (8)
C1A—C2A—C3A—N3A	−140.72 (9)	C9B—C5B—C6B—C8B	44.75 (11)
N2A—C5A—C6A—C7A	66.87 (12)	N2B—C5B—C9B—O4B	132.46 (9)
N2A—C5A—C6A—C8A	−59.32 (12)	C6B—C5B—C9B—O4B	−105.04 (10)
C4A—C1A—C2A—C3A	170.09 (8)	C6B—C5B—C9B—O3B	73.63 (11)
C5A—N2A—C4A—O1A	−11.79 (15)	N1C—C1C—C4C—N2C	168.50 (8)
N1A—C1A—C4A—O1A	−24.29 (12)	C1C—C4C—N2C—C5C	−172.04 (8)
C2A—C1A—C4A—O1A	95.96 (10)	C4C—N2C—C5C—C9C	−59.81 (11)
C2A—C1A—C4A—N2A	−81.83 (10)	N2C—C5C—C9C—O3C	140.32 (8)
C4A—N2A—C5A—C6A	150.36 (9)	N1C—C1C—C2C—C3C	−69.38 (10)
C9A—C5A—C6A—C8A	174.97 (9)	C1C—C2C—C3C—O2C	31.02 (13)
C9A—C5A—C6A—C7A	−58.83 (12)	C1C—C2C—C3C—N3C	−150.60 (9)
N2A—C5A—C9A—O4A	−174.35 (9)	N2C—C5C—C6C—C7C	−62.23 (11)
C6A—C5A—C9A—O4A	−48.31 (12)	N2C—C5C—C6C—C8C	176.15 (9)
C6A—C5A—C9A—O3A	132.48 (10)	C4C—C1C—C2C—C3C	169.75 (8)
N1B—C1B—C4B—N2B	156.04 (8)	C5C—N2C—C4C—O1C	6.44 (14)
C1B—C4B—N2B—C5B	171.65 (8)	N1C—C1C—C4C—O1C	−9.99 (13)
C4B—N2B—C5B—C9B	−129.34 (9)	C2C—C1C—C4C—O1C	112.25 (11)
N2B—C5B—C9B—O3B	−48.87 (11)	C2C—C1C—C4C—N2C	−69.26 (11)
N1B—C1B—C2B—C3B	−83.00 (10)	C4C—N2C—C5C—C6C	175.61 (8)
C1B—C2B—C3B—O2B	2.05 (14)	C9C—C5C—C6C—C7C	173.71 (9)
C1B—C2B—C3B—N3B	−176.72 (9)	C9C—C5C—C6C—C8C	52.09 (12)
N2B—C5B—C6B—C7B	−72.40 (10)	N2C—C5C—C9C—O4C	−41.54 (12)
N2B—C5B—C6B—C8B	165.61 (9)	C6C—C5C—C9C—O4C	82.24 (11)
C4B—C1B—C2B—C3B	156.97 (8)	C6C—C5C—C9C—O3C	−95.91 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O3C^i	0.997 (17)	1.750 (17)	2.7454 (11)	176.4 (16)
N1A—H2A···O2A	0.873 (18)	2.202 (18)	2.8782 (11)	134.1 (15)
N1A—H3A···O3A^ii	0.916 (18)	1.886 (18)	2.7909 (12)	168.9 (16)
N2A—H4A···O2W	0.841 (17)	2.168 (17)	3.0056 (13)	173.5 (16)
N3A—H5A···O3B	0.865 (18)	1.989 (18)	2.8381 (12)	166.7 (16)
N3A—H6A···O1A^iii	0.863 (17)	2.068 (17)	2.9085 (12)	164.4 (16)
C1A—H11A···O2C	1.00	2.51	3.4344 (12)	153
N1B—H1B···O1C^iv	0.842 (18)	1.906 (18)	2.7377 (11)	169.3 (17)
N1B—H2B···O3W^v	0.927 (18)	2.262 (18)	2.9573 (13)	131.3 (14)
N1B—H3B···O4A^ii	0.839 (18)	2.100 (18)	2.7441 (13)	133.3 (17)
N2B—H4B···O2A	0.887 (17)	2.112 (17)	2.9721 (11)	163.0 (16)
N3B—H5B···O4B^i	0.842 (18)	2.100 (18)	2.9199 (12)	164.7 (18)
N3B—H6B···O4W^v	0.905 (19)	1.889 (19)	2.7874 (15)	172.2 (17)
C1B—H11B···O4A^ii	1.00	2.43	3.0333 (12)	119
N1C—H1C···O2B^vi	0.896 (19)	2.112 (19)	2.9270 (13)	150.8 (15)
N1C—H2C···O2C	0.909 (18)	2.060 (18)	2.7522 (12)	131.9 (15)
N1C—H3C···O3B	0.936 (18)	1.858 (18)	2.7879 (12)	171.9 (16)
N2C—H4C···O1B^i	0.873 (16)	2.106 (16)	2.9317 (11)	157.5 (15)
N3C—H5C···O4C^i	0.923 (19)	2.056 (19)	2.9786 (13)	177.9 (17)
N3C—H6C···O4B^i	0.873 (19)	2.198 (19)	3.0205 (13)	156.9 (16)
C1C—H11C···O3W	1.00	2.25	3.1572 (13)	150
C8C—H83C···O1A^v	0.98	2.52	3.4126 (16)	152
O1W—H11W···O2C	0.82 (2)	2.04 (3)	2.7936 (13)	153 (2)
O1W—H12W···O3C^vii	0.88 (3)	1.90 (3)	2.7778 (14)	176 (2)
O2W—H21W···O3A^iii	0.87 (2)	2.03 (3)	2.8957 (14)	171 (2)
O2W—H22W···O1W	0.86 (2)	2.00 (2)	2.8512 (15)	170 (2)
O3W—H31W···O2B^vi	0.94 (2)	1.92 (2)	2.8390 (12)	164.0 (19)
O3W—H32W···O3C^vii	0.90 (2)	1.90 (2)	2.7896 (12)	168 (2)
O4W—H41W···O4C^i	0.77 (3)	2.00 (3)	2.7558 (15)	170 (3)
O4W—H42W···O1W	0.91 (3)	1.98 (3)	2.8508 (17)	160 (2)

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