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The crystal structure of the free acid form of NAD+ tetrahydrate (nicotin­amide adenine dinucleotide tetrahydrate or 3-carbamoyl-1-β-D-ribo­furan­osyl­pyridinium hydro­xide 5′-ester with adenosine 5′-pyrophosphate inner salt tetrahydrate, C21H27N7O14P2·4H2O) has been determined at 100 K. NAD+ is the coenzyme of several protein families and plays a dominant role in biological redox processes. In this study, the mol­ecule shows a different conformation from the one usually found in holoenzyme complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001220/gs1072sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001220/gs1072Isup2.hkl
Contains datablock I

CCDC reference: 146077

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

β-Nicotinamide Adenine Dinucleotide top
Crystal data top
C21H27N7O4P2·4(H2O)Z = 1
Mr = 735.50F(000) = 384
Triclinic, P1Dx = 1.579 Mg m3
a = 8.592 (10) ÅMo Kα radiation, λ = 0.70900 Å
b = 8.845 (10) ÅCell parameters from 141 reflections
c = 11.192 (10) Åθ = 3.0–19.0°
α = 109.64 (5)°µ = 0.23 mm1
β = 90.56 (5)°T = 100 K
γ = 103.92 (5)°Irregular, colourless
V = 773.7 (14) Å30.41 × 0.35 × 0.3 mm
Data collection top
Nonius KappaCCD
diffractometer
7439 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 36.3°, θmin = 2.5°
oscillation scansh = 014
15736 measured reflectionsk = 1414
7459 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052H atoms treated by a mixture of independent and constrained refinement
S = 1.01Calculated w = 1/[σ2(Fo2) + (0.0371P)2 + 0.0533P]
where P = (Fo2 + 2Fc2)/3
7459 reflections(Δ/σ)max = 0.001
573 parametersΔρmax = 0.32 e Å3
15 restraintsΔρmin = 0.25 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.09222 (7)0.20496 (7)0.23359 (6)0.01127 (9)
P10.22886 (2)0.29706 (2)0.187743 (17)0.00871 (3)
O20.16635 (8)0.48234 (8)0.14639 (6)0.01377 (9)
O30.31006 (7)0.23175 (8)0.09062 (6)0.01284 (9)
O40.34589 (7)0.22830 (8)0.31680 (5)0.01148 (9)
C10.49237 (9)0.28327 (10)0.30853 (7)0.01192 (11)
HC1A0.578 (2)0.205 (2)0.2914 (18)0.021 (4)*
HC1B0.476 (3)0.382 (3)0.246 (2)0.028 (5)*
C20.53848 (8)0.29898 (9)0.43348 (7)0.00979 (10)
HC20.633 (2)0.337 (2)0.4226 (19)0.021 (4)*
C30.40805 (8)0.41017 (9)0.48088 (7)0.00971 (10)
HC30.334 (2)0.494 (2)0.4130 (19)0.022 (4)*
O60.48866 (7)0.48042 (7)0.55255 (6)0.01263 (9)
HO60.425 (2)0.563 (2)0.5603 (16)0.015 (3)*
C40.32408 (8)0.28576 (9)0.56760 (7)0.00957 (10)
HC40.251 (2)0.268 (2)0.5181 (17)0.013 (3)*
O70.24503 (7)0.34097 (8)0.66095 (6)0.01364 (9)
HO70.154 (3)0.315 (3)0.674 (2)0.034 (5)*
C50.46680 (9)0.13013 (9)0.62506 (7)0.00988 (10)
HC50.512 (2)0.128 (2)0.7019 (19)0.020 (4)*
O50.57844 (7)0.13590 (7)0.53335 (6)0.01170 (9)
N10.42122 (8)0.02677 (8)0.65298 (6)0.01029 (9)
C60.38847 (9)0.12487 (9)0.76831 (7)0.01057 (10)
N20.39494 (9)0.09973 (9)0.88112 (7)0.01350 (11)
C70.35170 (11)0.21523 (10)0.97369 (7)0.01379 (12)
HC70.340 (2)0.208 (3)1.0502 (19)0.021 (4)*
N30.30738 (9)0.34757 (9)0.96171 (6)0.01252 (10)
HN30.274 (2)0.412 (2)1.0344 (18)0.020 (4)*
C80.30890 (9)0.38055 (9)0.85082 (7)0.01079 (10)
N50.27135 (9)0.51567 (9)0.84829 (7)0.01393 (11)
HN5A0.266 (2)0.592 (3)0.919 (2)0.022 (4)*
HN5B0.270 (3)0.539 (3)0.777 (2)0.028 (5)*
C90.35083 (9)0.25872 (9)0.74704 (7)0.01035 (10)
N40.36277 (8)0.24590 (8)0.62154 (6)0.01088 (9)
C100.40470 (9)0.10543 (9)0.56878 (7)0.01111 (11)
HC100.422 (2)0.061 (2)0.4802 (18)0.017 (4)*
P20.067929 (19)0.24839 (2)0.305121 (16)0.00809 (3)
O80.02441 (8)0.30033 (8)0.41150 (6)0.01280 (9)
O90.20305 (7)0.35642 (7)0.20699 (6)0.01254 (9)
O100.09903 (7)0.06741 (7)0.35813 (6)0.01092 (9)
C110.01603 (10)0.05681 (10)0.45951 (8)0.01462 (12)
H11A0.125 (2)0.061 (2)0.4381 (19)0.023 (4)*
H11B0.002 (3)0.030 (3)0.543 (2)0.032 (5)*
C120.01570 (9)0.22370 (9)0.48058 (7)0.01104 (10)
HC120.054 (2)0.301 (2)0.5567 (16)0.014 (3)*
C130.19323 (9)0.22439 (9)0.49128 (7)0.01091 (11)
HC130.256 (2)0.130 (2)0.5133 (18)0.016 (3)*
O120.21141 (9)0.37699 (8)0.57863 (6)0.01525 (10)
HO120.222 (3)0.357 (3)0.648 (2)0.034 (5)*
C140.25174 (9)0.21269 (9)0.35781 (7)0.01027 (10)
HC140.285 (2)0.102 (2)0.3040 (18)0.018 (4)*
O130.37894 (8)0.28780 (9)0.35705 (6)0.01635 (11)
HO130.372 (3)0.357 (3)0.434 (2)0.028 (5)*
C150.09715 (9)0.29943 (9)0.31379 (7)0.01056 (10)
HC150.079 (2)0.414 (2)0.3340 (16)0.012 (3)*
O110.03325 (7)0.27523 (8)0.37342 (6)0.01362 (9)
N60.09383 (8)0.22511 (8)0.17216 (6)0.01059 (9)
C160.03118 (10)0.09397 (10)0.12053 (7)0.01339 (11)
HC160.011 (2)0.062 (3)0.1804 (19)0.023 (4)*
C170.03108 (11)0.02816 (11)0.01045 (8)0.01503 (12)
HC170.018 (3)0.059 (3)0.040 (2)0.028 (5)*
C180.09276 (10)0.09956 (10)0.08761 (7)0.01397 (12)
HC180.090 (3)0.061 (3)0.180 (2)0.026 (4)*
C190.15467 (9)0.23635 (9)0.03126 (7)0.01146 (11)
C210.21200 (10)0.31981 (10)0.11383 (7)0.01391 (12)
O140.22790 (11)0.24830 (10)0.23135 (6)0.02096 (13)
N70.24234 (11)0.46731 (10)0.05732 (7)0.01766 (13)
HN7A0.268 (3)0.524 (3)0.107 (2)0.033 (5)*
HN7B0.218 (2)0.526 (3)0.0270 (19)0.023 (4)*
C200.15538 (9)0.29574 (9)0.10009 (7)0.01118 (10)
HC200.190 (2)0.386 (2)0.1476 (16)0.015 (3)*
OW10.56459 (9)0.10609 (9)0.03125 (8)0.01913 (12)
HW1B0.514 (2)0.042 (2)0.0627 (18)0.024 (4)*
HW1A0.492 (3)0.158 (3)0.015 (2)0.048 (7)*
OW20.30386 (9)0.33492 (9)0.78751 (7)0.01745 (11)
HW2A0.353 (3)0.260 (3)0.846 (2)0.056 (8)*
HW2B0.374 (2)0.377 (2)0.7138 (13)0.024 (4)*
OW30.01426 (8)0.21778 (9)0.67140 (6)0.01693 (11)
HW3A0.1068 (19)0.270 (3)0.701 (2)0.035 (5)*
HW3B0.033 (2)0.253 (2)0.5821 (9)0.022 (4)*
OW40.32682 (9)0.11814 (10)0.21374 (8)0.02130 (12)
HW4A0.326 (3)0.0036 (14)0.179 (2)0.044 (6)*
HW4B0.434 (2)0.170 (4)0.258 (4)0.095 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0102 (2)0.0129 (2)0.0139 (2)0.00574 (17)0.00464 (16)0.00665 (18)
P10.00939 (6)0.00918 (7)0.00797 (6)0.00338 (5)0.00286 (5)0.00277 (5)
O20.0150 (2)0.0093 (2)0.0157 (2)0.00289 (17)0.00514 (18)0.00267 (18)
O30.0146 (2)0.0145 (2)0.0102 (2)0.00347 (18)0.00536 (17)0.00531 (18)
O40.0113 (2)0.0149 (2)0.0092 (2)0.00720 (17)0.00166 (16)0.00280 (17)
C10.0113 (2)0.0161 (3)0.0110 (3)0.0074 (2)0.0034 (2)0.0053 (2)
C20.0103 (2)0.0095 (2)0.0105 (2)0.00427 (19)0.00205 (19)0.0033 (2)
C30.0103 (2)0.0084 (2)0.0109 (2)0.00356 (19)0.00152 (19)0.00315 (19)
O60.0137 (2)0.0107 (2)0.0170 (2)0.00564 (17)0.00253 (18)0.00752 (18)
C40.0102 (2)0.0098 (2)0.0104 (2)0.00381 (19)0.00276 (19)0.0048 (2)
O70.0142 (2)0.0171 (2)0.0152 (2)0.00719 (19)0.00654 (18)0.0105 (2)
C50.0120 (2)0.0084 (2)0.0099 (2)0.0048 (2)0.00145 (19)0.0027 (2)
O50.0110 (2)0.0094 (2)0.0127 (2)0.00214 (16)0.00365 (17)0.00165 (17)
N10.0141 (2)0.0084 (2)0.0093 (2)0.00527 (18)0.00211 (18)0.00263 (18)
C60.0142 (3)0.0091 (2)0.0096 (2)0.0050 (2)0.0028 (2)0.0035 (2)
N20.0201 (3)0.0123 (2)0.0110 (2)0.0077 (2)0.0044 (2)0.0053 (2)
C70.0204 (3)0.0127 (3)0.0109 (3)0.0077 (2)0.0045 (2)0.0049 (2)
N30.0180 (3)0.0113 (2)0.0104 (2)0.0070 (2)0.0043 (2)0.00425 (19)
C80.0136 (3)0.0093 (2)0.0099 (2)0.0045 (2)0.0021 (2)0.0027 (2)
N50.0224 (3)0.0106 (2)0.0112 (2)0.0089 (2)0.0035 (2)0.0035 (2)
C90.0136 (3)0.0087 (2)0.0093 (2)0.0048 (2)0.0020 (2)0.0026 (2)
N40.0147 (2)0.0093 (2)0.0092 (2)0.00473 (19)0.00139 (18)0.00280 (18)
C100.0149 (3)0.0100 (3)0.0092 (2)0.0050 (2)0.0011 (2)0.0032 (2)
P20.00893 (6)0.00745 (6)0.00837 (6)0.00350 (5)0.00186 (5)0.00238 (5)
O80.0176 (2)0.0127 (2)0.0113 (2)0.00630 (18)0.00307 (17)0.00651 (18)
O90.0114 (2)0.0109 (2)0.0122 (2)0.00306 (17)0.00031 (17)0.00005 (17)
O100.0121 (2)0.00812 (19)0.0116 (2)0.00513 (16)0.00118 (16)0.00048 (16)
C110.0180 (3)0.0100 (3)0.0138 (3)0.0063 (2)0.0054 (2)0.0001 (2)
C120.0148 (3)0.0090 (2)0.0088 (2)0.0039 (2)0.0007 (2)0.0020 (2)
C130.0156 (3)0.0095 (2)0.0089 (2)0.0053 (2)0.0028 (2)0.0034 (2)
O120.0248 (3)0.0132 (2)0.0093 (2)0.0105 (2)0.00389 (19)0.00196 (18)
C140.0123 (2)0.0098 (2)0.0091 (2)0.0048 (2)0.00157 (19)0.0026 (2)
O130.0167 (2)0.0198 (3)0.0140 (2)0.0115 (2)0.00120 (19)0.0031 (2)
C150.0147 (3)0.0086 (2)0.0082 (2)0.0030 (2)0.0011 (2)0.00268 (19)
O110.0120 (2)0.0176 (2)0.0117 (2)0.00262 (18)0.00028 (17)0.00651 (19)
N60.0142 (2)0.0090 (2)0.0087 (2)0.00324 (19)0.00212 (18)0.00317 (18)
C160.0174 (3)0.0122 (3)0.0120 (3)0.0066 (2)0.0031 (2)0.0040 (2)
C170.0198 (3)0.0144 (3)0.0118 (3)0.0082 (2)0.0040 (2)0.0030 (2)
C180.0179 (3)0.0131 (3)0.0100 (3)0.0049 (2)0.0029 (2)0.0023 (2)
C190.0152 (3)0.0103 (3)0.0082 (2)0.0025 (2)0.0012 (2)0.0029 (2)
C210.0189 (3)0.0132 (3)0.0092 (3)0.0032 (2)0.0001 (2)0.0040 (2)
O140.0358 (4)0.0190 (3)0.0080 (2)0.0093 (3)0.0002 (2)0.0030 (2)
N70.0292 (4)0.0148 (3)0.0101 (2)0.0090 (3)0.0011 (2)0.0035 (2)
C200.0157 (3)0.0096 (2)0.0087 (2)0.0037 (2)0.0017 (2)0.0034 (2)
OW10.0176 (3)0.0203 (3)0.0251 (3)0.0078 (2)0.0093 (2)0.0129 (2)
OW20.0193 (3)0.0194 (3)0.0152 (2)0.0092 (2)0.0008 (2)0.0052 (2)
OW30.0162 (2)0.0207 (3)0.0143 (2)0.0064 (2)0.00351 (19)0.0053 (2)
OW40.0199 (3)0.0199 (3)0.0244 (3)0.0045 (2)0.0003 (2)0.0088 (3)
Geometric parameters (Å, º) top
O1—P11.580 (2)O10—C111.4453 (18)
O1—P21.630 (2)C11—C121.507 (2)
P1—O31.498 (1)C11—H11A0.96 (2)
P1—O21.500 (2)C11—H11B1.03 (2)
P1—O41.598 (2)C12—O111.4520 (15)
O4—C11.448 (2)C12—C131.533 (2)
C1—C21.509 (2)C12—HC120.98 (2)
C1—HC1A0.95 (2)C13—O121.4210 (17)
C1—HC1B0.90 (2)C13—C141.5333 (17)
C2—O51.4553 (18)C13—HC130.99 (2)
C2—C31.5286 (16)O12—HO120.86 (2)
C2—HC20.94 (2)C14—O131.4102 (16)
C3—O61.4285 (14)C14—C151.5403 (18)
C3—C41.5333 (16)C14—HC140.93 (2)
C3—HC30.96 (2)O13—HO130.86 (2)
O6—HO60.83 (2)C15—O111.3940 (16)
C4—O71.4103 (14)C15—N61.502 (2)
C4—C51.5457 (19)C15—HC150.93 (2)
C4—HC40.91 (2)N6—C201.345 (1)
O7—HO70.86 (2)N6—C161.351 (2)
C5—O51.4085 (15)C16—C171.384 (2)
C5—N11.466 (2)C16—HC160.91 (2)
C5—HC50.93 (2)C17—C181.394 (2)
N1—C61.367 (2)C17—HC170.93 (2)
N1—C101.371 (1)C18—C191.396 (2)
C6—N21.356 (2)C18—HC180.97 (2)
C6—C91.391 (2)C19—C201.386 (2)
N2—C71.317 (2)C19—C211.505 (2)
C7—N31.361 (2)C21—O141.243 (2)
C7—HC70.88 (2)C21—N71.335 (2)
N3—C81.367 (2)N7—HN7A0.92 (2)
N3—HN30.91 (2)N7—HN7B0.91 (2)
C8—N51.320 (2)C20—HC200.92 (2)
C8—C91.412 (2)OW1—HW1B0.937 (9)
N5—HN5A0.86 (2)OW1—HW1A0.94 (1)
N5—HN5B0.89 (2)OW2—HW2A0.95 (1)
C9—N41.378 (2)OW2—HW2B0.926 (9)
N4—C101.322 (2)OW3—HW3A0.94 (1)
C10—HC100.96 (2)OW3—HW3B0.941 (9)
P2—O91.484 (2)OW4—HW4A0.95 (1)
P2—O81.487 (1)OW4—HW4B0.97 (1)
P2—O101.599 (2)
P1—O1—P2132.45 (7)O9—P2—O10107.15 (8)
O3—P1—O2115.86 (7)O8—P2—O10110.97 (7)
O3—P1—O1107.14 (7)O9—P2—O1108.60 (9)
O2—P1—O1112.13 (8)O8—P2—O1108.98 (7)
O3—P1—O4109.93 (8)O10—P2—O198.58 (7)
O2—P1—O4110.20 (7)C11—O10—P2116.34 (8)
O1—P1—O4100.45 (8)O10—C11—C12108.51 (9)
C1—O4—P1115.82 (8)O10—C11—H11A111.3 (12)
O4—C1—C2109.59 (7)C12—C11—H11A108.8 (12)
O4—C1—HC1A110.3 (12)O10—C11—H11B109.9 (13)
C2—C1—HC1A108.7 (12)C12—C11—H11B109.0 (13)
O4—C1—HC1B109.4 (14)H11A—C11—H11B109.3 (17)
C2—C1—HC1B109.5 (14)O11—C12—C11108.96 (8)
HC1A—C1—HC1B109 (2)O11—C12—C13106.98 (7)
O5—C2—C1109.62 (10)C11—C12—C13114.01 (8)
O5—C2—C3106.11 (9)O11—C12—HC12108.2 (10)
C1—C2—C3115.44 (9)C11—C12—HC12105.9 (10)
O5—C2—HC2107.9 (12)C13—C12—HC12112.7 (10)
C1—C2—HC2106.3 (12)O12—C13—C12112.06 (9)
C3—C2—HC2111.3 (12)O12—C13—C14107.29 (9)
O6—C3—C2106.99 (10)C12—C13—C14103.17 (8)
O6—C3—C4111.17 (9)O12—C13—HC13110.6 (11)
C2—C3—C4102.48 (10)C12—C13—HC13112.3 (10)
O6—C3—HC3111.7 (12)C14—C13—HC13111.1 (11)
C2—C3—HC3112.8 (12)C13—O12—HO12102.7 (16)
C4—C3—HC3111.3 (12)O13—C14—C13113.55 (8)
C3—O6—HO6109.8 (12)O13—C14—C15112.79 (10)
O7—C4—C3113.11 (9)C13—C14—C15102.22 (9)
O7—C4—C5112.96 (9)O13—C14—HC14108.8 (12)
C3—C4—C5101.54 (11)C13—C14—HC14110.4 (11)
O7—C4—HC4109.3 (11)C15—C14—HC14108.9 (12)
C3—C4—HC4108.4 (11)C14—O13—HO13104.6 (14)
C5—C4—HC4111.3 (11)O11—C15—N6108.26 (9)
C4—O7—HO7113.0 (16)O11—C15—C14107.50 (10)
O5—C5—N1107.33 (8)N6—C15—C14111.30 (9)
O5—C5—C4106.98 (9)O11—C15—HC15106.4 (10)
N1—C5—C4113.55 (10)N6—C15—HC15107.1 (10)
O5—C5—HC5112.1 (12)C14—C15—HC15116.0 (10)
N1—C5—HC5106.5 (12)C15—O11—C12110.42 (9)
C4—C5—HC5110.5 (12)C20—N6—C16122.02 (9)
C5—O5—C2110.28 (8)C20—N6—C15116.82 (9)
C6—N1—C10106.23 (10)C16—N6—C15121.16 (7)
C6—N1—C5126.99 (8)N6—C16—C17119.53 (8)
C10—N1—C5126.78 (8)N6—C16—HC16112.9 (13)
N2—C6—N1127.35 (9)C17—C16—HC16127.5 (13)
N2—C6—C9126.83 (8)C16—C17—C18119.78 (10)
N1—C6—C9105.80 (9)C16—C17—HC17115.8 (13)
C7—N2—C6112.19 (10)C18—C17—HC17124.3 (13)
N2—C7—N3125.41 (9)C17—C18—C19119.31 (9)
N2—C7—HC7121.8 (13)C17—C18—HC18122.4 (12)
N3—C7—HC7112.6 (13)C19—C18—HC18118.3 (12)
C7—N3—C8123.37 (8)C20—C19—C18118.86 (8)
C7—N3—HN3113.8 (12)C20—C19—C21121.80 (9)
C8—N3—HN3122.8 (12)C18—C19—C21119.29 (9)
N5—C8—N3119.80 (8)O14—C21—N7123.24 (9)
N5—C8—C9126.39 (9)O14—C21—C19118.32 (10)
N3—C8—C9113.81 (9)N7—C21—C19118.44 (10)
C8—N5—HN5A119.0 (14)C21—N7—HN7A119.3 (15)
C8—N5—HN5B121.3 (14)C21—N7—HN7B123.5 (13)
HN5A—N5—HN5B118.6 (19)HN7A—N7—HN7B116 (2)
N4—C9—C6110.62 (8)N6—C20—C19120.48 (9)
N4—C9—C8131.16 (8)N6—C20—HC20112.8 (11)
C6—C9—C8118.22 (9)C19—C20—HC20126.7 (11)
C10—N4—C9104.11 (8)HW1B—OW1—HW1A109.0 (19)
N4—C10—N1113.24 (9)HW2A—OW2—HW2B104 (2)
N4—C10—HC10124.1 (11)HW3A—OW3—HW3B107.1 (18)
N1—C10—HC10122.6 (11)HW4A—OW4—HW4B103 (3)
O9—P2—O8120.34 (8)
P2—O1—P1—O3160.9 (1)C8—C9—N4—C10179.33 (8)
P2—O1—P1—O232.7 (1)C9—N4—C10—N10.23 (9)
P2—O1—P1—O484.3 (1)C6—N1—C10—N40.43 (9)
O3—P1—O4—C164.8 (1)C5—N1—C10—N4179.77 (7)
O2—P1—O4—C164.1 (1)P1—O1—P2—O987.7 (1)
O1—P1—O4—C1177.5 (1)P1—O1—P2—O845.2 (1)
P1—O4—C1—C2147.2 (1)P1—O1—P2—O10160.9 (1)
O4—C1—C2—O564.9 (1)O9—P2—O10—C11177.5 (1)
O4—C1—C2—C354.81 (11)O8—P2—O10—C1144.3 (1)
O5—C2—C3—O688.45 (10)O1—P2—O10—C1169.9 (1)
C1—C2—C3—O6149.92 (7)P2—O10—C11—C12170.2 (1)
O5—C2—C3—C428.58 (8)O10—C11—C12—O1171.3 (1)
C1—C2—C3—C493.06 (10)O10—C11—C12—C1348.1 (1)
O6—C3—C4—O741.97 (10)O11—C12—C13—O1294.00 (11)
C2—C3—C4—O7155.96 (7)C11—C12—C13—O12145.48 (8)
O6—C3—C4—C579.36 (10)O11—C12—C13—C1421.10 (8)
C2—C3—C4—C534.63 (8)C11—C12—C13—C1499.42 (9)
O7—C4—C5—O5151.39 (7)O12—C13—C14—O1332.88 (9)
C3—C4—C5—O529.95 (7)C12—C13—C14—O13151.36 (7)
O7—C4—C5—N190.40 (9)O12—C13—C14—C1588.89 (10)
C3—C4—C5—N1148.17 (7)C12—C13—C14—C1529.58 (8)
N1—C5—O5—C2134.87 (9)O13—C14—C15—O11151.64 (7)
C4—C5—O5—C212.67 (7)C13—C14—C15—O1129.34 (8)
C1—C2—O5—C5115.11 (9)O13—C14—C15—N689.96 (10)
C3—C2—O5—C510.19 (7)C13—C14—C15—N6147.74 (7)
O5—C5—N1—C6144.2 (1)N6—C15—O11—C12137.18 (8)
C4—C5—N1—C697.79 (11)C14—C15—O11—C1216.83 (8)
O5—C5—N1—C1035.01 (11)C11—C12—O11—C15120.80 (9)
C4—C5—N1—C1083.00 (11)C13—C12—O11—C152.90 (8)
C10—N1—C6—N2177.65 (8)O11—C15—N6—C20150.33 (7)
C5—N1—C6—N21.68 (13)C14—C15—N6—C2091.73 (12)
C10—N1—C6—C90.89 (8)O11—C15—N6—C1629.43 (10)
C5—N1—C6—C9179.77 (7)C14—C15—N6—C1688.52 (12)
N1—C6—N2—C7178.19 (8)C20—N6—C16—C170.65 (12)
C9—C6—N2—C73.6 (1)C15—N6—C16—C17179.61 (7)
C6—N2—C7—N30.97 (13)N6—C16—C17—C181.18 (13)
N2—C7—N3—C82.83 (14)C16—C17—C18—C190.33 (13)
C7—N3—C8—N5176.85 (8)C17—C18—C19—C201.04 (12)
C7—N3—C8—C93.86 (11)C17—C18—C19—C21176.32 (8)
N2—C6—C9—N4177.47 (8)C20—C19—C21—O14170.77 (8)
N1—C6—C9—N41.09 (9)C18—C19—C21—O1411.95 (12)
N2—C6—C9—C82.4 (1)C20—C19—C21—N79.6 (1)
N1—C6—C9—C8179.04 (7)C18—C19—C21—N7167.67 (8)
N5—C8—C9—N40.49 (14)C16—N6—C20—C190.76 (12)
N3—C8—C9—N4178.74 (8)C15—N6—C20—C19178.99 (7)
N5—C8—C9—C6179.35 (8)C18—C19—C20—N61.59 (11)
N3—C8—C9—C61.42 (10)C21—C19—C20—N6175.69 (7)
C6—C9—N4—C100.82 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—HO6···N4i0.83 (2)1.99 (2)2.764 (3)154 (2)
O7—HO7···OW30.86 (2)1.86 (2)2.693 (3)161 (2)
O12—HO12···O14ii0.86 (2)1.90 (2)2.719 (2)161 (2)
O13—HO13···O120.86 (2)2.05 (2)2.629 (3)124 (2)
O13—HO13···O6iii0.86 (2)2.20 (2)2.905 (3)139 (2)
N3—HN3···O2iv0.91 (2)1.72 (2)2.615 (2)165 (2)
N5—HN5A···O3iv0.86 (2)1.99 (2)2.830 (3)166 (2)
N5—HN5B···O7v0.89 (2)1.97 (2)2.823 (2)159 (2)
N7—HN7A···OW2vi0.92 (2)2.06 (2)2.971 (2)174 (2)
N7—HN7B···O9v0.91 (2)1.92 (2)2.815 (3)171 (2)
OW1—HW1A···O30.94 (1)1.87 (1)2.790 (3)164 (2)
OW1—HW1B···N2vii0.94 (1)2.04 (1)2.975 (3)176 (2)
OW2—HW2A···OW1viii0.95 (1)1.86 (1)2.806 (3)175 (3)
OW2—HW2B···O6ix0.93 (1)1.95 (1)2.877 (3)175 (2)
OW3—HW3A···OW20.94 (1)2.02 (1)2.947 (3)168 (2)
OW3—HW3B···O80.94 (1)1.82 (1)2.746 (3)168 (2)
OW4—HW4A···O30.95 (1)1.95 (1)2.900 (4)173 (2)
OW4—HW4B···O13x0.97 (1)1.81 (1)2.773 (3)172 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y, z+1; (iii) x1, y+1, z; (iv) x, y+1, z+1; (v) x, y+1, z; (vi) x, y+1, z1; (vii) x, y, z1; (viii) x1, y, z+1; (ix) x1, y, z; (x) x+1, y, z.
 

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