Disodium cytidine-5′-monophosphate 6.07-hydrate methanol 0.27-solvate

Gonzalez, S.V.; Larsen, K.; Nelson, W.H.; Sagstuen, E.; Görbitz, C.H.

doi:10.1107/S160053680500471X

Disodium cytidine-5'-monophosphate 6.07-hydrate methanol 0.27-solvate

S. V. Gonzalez, K. Larsen, W. H. Nelson, E. Sagstuen and C. H. Görbitz

The crystal structure of the title complex, Na₂⁺·C₉H₁₂N₃O₈P^-·6.07H₂O·0.27CH₄O, in space group P2₁2₁2₁ is remarkably similar to the monoclinic P2₁ structure of sodium cytidine-5'-monophosphate 6.5 hydrate [Borodi et al. (2001). Acta Cryst. E57, m514-m516].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500471X/hb6154sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680500471X/hb6154Isup2.hkl Contains datablock I

CCDC reference: 269782

checkCIF report

Key indicators

Single-crystal X-ray study
T = 105 K
Mean (C-C) = 0.001 Å
H-atom completeness 100%
Disorder in solvent or counterion
R factor = 0.034
wR factor = 0.092
Data-to-parameter ratio = 39.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT780_ALERT_1_A Coordinates do not Form a Properly Connected Set          ?

Author Response: This error message probably appears because coordination of the sodium ions in the structure extends beyond the asymmetric unit, in fact infinte chains are formed in the crystal.


Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm
PLAT430_ALERT_2_B Short Inter D...A Contact  O2M    ..  O2PB    ..       2.68 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O11W   ..  O1PB    ..       2.65 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O1PB   ..  O31W    ..       2.68 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O1PB   ..  O21W    ..       2.77 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2PB   ..  O3M     ..       2.71 Ang.

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 ............       0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.15
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          4
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O8W
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      37.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O2M
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      >O11W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      >O22W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O1M
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O3M
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O12W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O21W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O31W
PLAT430_ALERT_2_C Short Inter D...A Contact  O2PB   ..  O1M     ..       2.88 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.41 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:   C9.25 H22 N3 Na2 O14.38 P1
            Atom count from _chemical_formula_moiety:C9.27 H25.22 N3 O14.34 P1
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C9.25 H22 N3 Na2 O14.38 P1
            Atom count from the _atom_site data:  C9.273 H21.89580 N3 Na2 O14.3798
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C9.25 H22 N3 Na2 O14.38 P
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         74.00     74.18   -0.18
           H        176.00    175.17    0.83
           N         24.00     24.00    0.00
           Na        16.00     16.00    0.00
           O        115.04    115.04    0.00
           P          8.00      8.00    0.00
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           40.29
           From the CIF: _reflns_number_total              24465
           Count of symmetry unique reflns        13732
           Completeness (_total/calc)            178.16%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured     10733
           Fraction of Friedel pairs measured     0.782
           Are heavy atom types Z>Si present          yes

   1 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  20 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

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

Computing details top

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

Disodium cytidine-5'-monophosphate 6.07-hydrate methanol 0.27-solvate top

Crystal data top

2Na⁺·C₉H₁₂N₃O₈P²⁻·6.07H₂O·0.27CH₄O	F(000) = 2004
M_r = 482.25	D_x = 1.595 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 43514 reflections
a = 8.9750 (1) Å	θ = 1.9–40.3°
b = 20.4196 (3) Å	µ = 0.26 mm⁻¹
c = 21.9152 (4) Å	T = 105 K
V = 4016.31 (10) Å³	Plate, colourless
Z = 8	1.00 × 0.80 × 0.15 mm

Data collection top

Siemens SMART CCD diffractometer	24465 independent reflections
Radiation source: fine-focus sealed tube	23085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.3 pixels mm^-1	θ_max = 40.3°, θ_min = 1.9°
ω scans	h = −16→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −36→36
T_min = 0.782, T_max = 0.962	l = −39→38
67367 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0485P)² + 0.6755P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.007
24465 reflections	Δρ_max = 0.90 e Å⁻³
627 parameters	Δρ_min = −0.42 e Å⁻³
13 restraints	Absolute structure: Flack (1983), 10733 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

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. 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 = 55°, crystal-to-detector distance 5.02 cm. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C2A	0.49350 (9)	0.72201 (4)	0.85400 (4)	0.01363 (11)
C4A	0.38572 (9)	0.77811 (4)	0.77263 (4)	0.01495 (12)
C5A	0.43060 (10)	0.72846 (4)	0.73028 (4)	0.01659 (12)
H51A	0.4074	0.7315	0.6881	0.020*
C6A	0.50730 (10)	0.67716 (4)	0.75304 (4)	0.01536 (12)
H61A	0.5402	0.6435	0.7263	0.018*
O5A	0.52375 (9)	0.71824 (4)	0.90964 (3)	0.01915 (11)
N1A	0.53853 (8)	0.67282 (3)	0.81415 (3)	0.01339 (10)
N3A	0.41430 (8)	0.77317 (4)	0.83231 (4)	0.01519 (11)
N4A	0.31536 (10)	0.83213 (4)	0.75339 (4)	0.02066 (13)
H41A	0.2898	0.8627	0.7797	0.025*
H42A	0.2947	0.8371	0.7144	0.025*
C1A'	0.62674 (9)	0.61751 (4)	0.83637 (3)	0.01307 (11)
H11A	0.6569	0.6256	0.8797	0.016*
C2A'	0.54754 (8)	0.55129 (4)	0.83165 (4)	0.01264 (11)
H21A	0.4851	0.5498	0.7939	0.015*
C3A'	0.67951 (9)	0.50365 (4)	0.82586 (4)	0.01411 (11)
H31A	0.6513	0.4642	0.8015	0.017*
C4A'	0.79730 (9)	0.54503 (4)	0.79218 (4)	0.01347 (11)
H43A	0.8963	0.5380	0.8121	0.016*
C5A'	0.81163 (9)	0.53046 (5)	0.72466 (4)	0.01616 (12)
H52A	0.8765	0.5635	0.7051	0.019*
H53A	0.8574	0.4868	0.7188	0.019*
O2A'	0.45812 (8)	0.54106 (4)	0.88350 (3)	0.01786 (11)
H2A'	0.371 (2)	0.5208 (10)	0.8775 (9)	0.027*
O3A'	0.72464 (9)	0.48584 (4)	0.88566 (3)	0.02197 (13)
H3A'	0.803 (3)	0.4708 (11)	0.8836 (10)	0.033*
O4A'	0.75518 (7)	0.61290 (3)	0.79936 (3)	0.01594 (10)
O5A'	0.66684 (7)	0.53181 (3)	0.69733 (3)	0.01477 (9)
P1A	0.64623 (2)	0.495991 (9)	0.631654 (9)	0.01024 (3)
O1PA	0.74260 (7)	0.53240 (3)	0.58556 (3)	0.01493 (9)
O2PA	0.48138 (7)	0.50387 (3)	0.61858 (3)	0.01463 (9)
O3PA	0.69538 (7)	0.42527 (3)	0.64020 (3)	0.01525 (9)
C2B	1.00138 (9)	0.70258 (4)	0.85807 (3)	0.01235 (10)
C4B	1.11409 (8)	0.64070 (4)	0.78193 (3)	0.01219 (10)
C5B	1.07874 (10)	0.68881 (4)	0.73652 (4)	0.01444 (12)
H51B	1.1086	0.6836	0.6952	0.017*
C6B	1.00121 (10)	0.74183 (4)	0.75495 (4)	0.01412 (11)
H61B	0.9735	0.7743	0.7260	0.017*
O5B	0.96468 (9)	0.71213 (3)	0.91256 (3)	0.01804 (11)
N1B	0.96210 (8)	0.74935 (3)	0.81490 (3)	0.01223 (10)
N3B	1.07851 (8)	0.64882 (3)	0.84094 (3)	0.01267 (10)
N4B	1.18284 (9)	0.58559 (4)	0.76548 (3)	0.01605 (11)
H41B	1.2038	0.5556	0.7930	0.019*
H42B	1.2073	0.5792	0.7271	0.019*
C1B'	0.86728 (9)	0.80420 (3)	0.83229 (3)	0.01167 (10)
H11B	0.8319	0.7982	0.8752	0.014*
C2B'	0.93997 (8)	0.87159 (4)	0.82550 (3)	0.01194 (10)
H21B	1.0023	0.8733	0.7877	0.014*
C3B'	0.80127 (9)	0.91463 (4)	0.81837 (4)	0.01349 (11)
H31B	0.8236	0.9566	0.7968	0.016*
C4B'	0.69507 (8)	0.87068 (4)	0.78160 (3)	0.01192 (10)
H43B	0.5922	0.8758	0.7985	0.014*
C5B'	0.68987 (9)	0.88359 (4)	0.71382 (4)	0.01517 (12)
H52B	0.6304	0.8491	0.6934	0.018*
H53B	0.6415	0.9264	0.7060	0.018*
O2B'	1.02664 (7)	0.88676 (3)	0.87732 (3)	0.01638 (10)
H2B'	1.108 (2)	0.9021 (9)	0.8661 (9)	0.025*
O3B'	0.74502 (8)	0.92514 (4)	0.87805 (3)	0.01995 (12)
H3B'	0.669 (2)	0.9447 (10)	0.8745 (9)	0.030*
O4B'	0.74354 (7)	0.80415 (3)	0.79190 (3)	0.01386 (9)
O5B'	0.83833 (7)	0.88401 (3)	0.68948 (3)	0.01468 (9)
P1B	0.86249 (2)	0.923675 (10)	0.626083 (9)	0.01106 (3)
O1PB	1.02850 (7)	0.91784 (3)	0.61431 (3)	0.01669 (10)
O2PB	0.76995 (8)	0.89015 (3)	0.57705 (3)	0.01689 (10)
O3PB	0.81160 (7)	0.99362 (3)	0.63757 (3)	0.01515 (9)
O1W	0.18181 (9)	0.35737 (4)	0.47733 (4)	0.02133 (12)
H11W	0.111 (2)	0.3485 (10)	0.4540 (10)	0.032*
H12W	0.224 (2)	0.3221 (11)	0.4870 (10)	0.032*
O2W	0.27545 (9)	0.59749 (4)	0.63812 (4)	0.02221 (13)
H21W	0.208 (2)	0.5900 (11)	0.6217 (10)	0.033*
H22W	0.345 (2)	0.5716 (11)	0.6368 (10)	0.033*
O3W	0.02385 (10)	0.56995 (6)	0.56850 (4)	0.0329 (2)
H31W	−0.061 (3)	0.5619 (13)	0.5796 (11)	0.049*
H32W	0.021 (3)	0.5808 (13)	0.5331 (12)	0.049*
O4W	0.31461 (9)	0.50441 (4)	0.50672 (3)	0.01874 (11)
H41W	0.371 (2)	0.5069 (10)	0.5372 (9)	0.028*
H42W	0.298 (2)	0.5377 (10)	0.4937 (9)	0.028*
O5W	−0.14707 (9)	0.45134 (4)	0.49768 (3)	0.02017 (11)
H51W	−0.145 (2)	0.4696 (10)	0.4639 (8)	0.030*
H52W	−0.186 (2)	0.4798 (10)	0.5225 (8)	0.030*
O6W	0.80948 (10)	0.26988 (4)	0.51857 (4)	0.02397 (13)
H61W	0.840 (3)	0.2748 (11)	0.4841 (10)	0.036*
H62W	0.889 (3)	0.2597 (11)	0.5398 (9)	0.036*
O7W	0.57803 (9)	0.38825 (4)	0.48666 (4)	0.02075 (12)
H71W	0.577 (2)	0.3533 (10)	0.4659 (10)	0.031*
H72W	0.648 (2)	0.4101 (9)	0.4807 (10)	0.031*
O8W	0.42070 (17)	0.69930 (5)	0.56888 (5)	0.0396 (3)
H81W	0.471 (3)	0.6760 (14)	0.5441 (13)	0.059*
H82W	0.367 (3)	0.6767 (14)	0.5860 (13)	0.059*
O9W	0.13061 (9)	0.87565 (3)	0.49615 (3)	0.01889 (11)
H91W	0.152 (2)	0.9036 (10)	0.4746 (8)	0.028*
H92W	0.086 (2)	0.8964 (10)	0.5272 (8)	0.028*
O10W	0.47421 (10)	0.88794 (5)	0.55296 (5)	0.02431 (17)	0.8958 (19)
H13W	0.455 (3)	0.9140 (13)	0.5661 (12)	0.036*	0.8958 (19)
H14W	0.572 (3)	0.8830 (12)	0.5609 (12)	0.036*	0.8958 (19)
O11W	0.2000 (2)	0.81398 (8)	0.63280 (8)	0.0253 (5)*	0.543 (6)
O21W	0.1528 (3)	0.79392 (14)	0.61870 (13)	0.0316 (8)*	0.377 (6)
O31W	0.2600 (8)	0.8361 (3)	0.6274 (3)	0.0288 (18)*	0.140 (5)
O12W	0.0891 (7)	0.7229 (3)	0.5673 (3)	0.0358 (16)*	0.217 (7)
O22W	0.0190 (4)	0.71299 (14)	0.58135 (14)	0.0504 (9)*	0.565 (8)
O1M	0.3512 (5)	0.74604 (14)	0.43073 (14)	0.0227 (8)*	0.293 (7)
O2M	0.2389 (3)	0.73922 (9)	0.43829 (8)	0.0267 (5)*	0.517 (6)
O3M	0.3016 (8)	0.74103 (19)	0.43757 (19)	0.0209 (12)*	0.212 (8)
C1M	0.2584 (4)	0.77267 (16)	0.38292 (15)	0.0401 (9)*	0.546 (9)
Na1	0.36712 (5)	0.42342 (2)	0.431472 (18)	0.01833 (7)
Na2	0.63946 (7)	0.33434 (2)	0.57762 (2)	0.02371 (8)
Na3	0.09597 (5)	0.44265 (2)	0.540733 (19)	0.01831 (7)
Na4	0.31314 (6)	0.79549 (2)	0.53142 (2)	0.02158 (11)	0.8958 (19)
Na4B	0.2273 (5)	0.7715 (2)	0.5368 (2)	0.0188 (9)*	0.1042 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2A	0.0148 (3)	0.0130 (3)	0.0131 (3)	−0.0004 (2)	0.0019 (2)	−0.0024 (2)
C4A	0.0140 (3)	0.0122 (3)	0.0187 (3)	0.0001 (2)	0.0006 (2)	0.0008 (2)
C5A	0.0190 (3)	0.0161 (3)	0.0147 (3)	0.0020 (2)	−0.0018 (2)	−0.0004 (2)
C6A	0.0180 (3)	0.0152 (3)	0.0129 (3)	0.0017 (2)	−0.0012 (2)	−0.0018 (2)
O5A	0.0253 (3)	0.0204 (3)	0.0118 (2)	0.0012 (2)	0.0005 (2)	−0.00375 (19)
N1A	0.0160 (3)	0.0132 (2)	0.0110 (2)	0.00194 (19)	−0.00095 (19)	−0.00207 (18)
N3A	0.0164 (3)	0.0125 (2)	0.0166 (3)	0.0009 (2)	0.0022 (2)	−0.0012 (2)
N4A	0.0216 (3)	0.0152 (3)	0.0252 (4)	0.0033 (2)	−0.0011 (3)	0.0024 (2)
C1A'	0.0129 (3)	0.0141 (3)	0.0122 (3)	0.0017 (2)	−0.0014 (2)	−0.0023 (2)
C2A'	0.0122 (3)	0.0144 (3)	0.0113 (3)	0.0008 (2)	−0.0004 (2)	−0.0003 (2)
C3A'	0.0163 (3)	0.0149 (3)	0.0111 (3)	0.0037 (2)	0.0005 (2)	−0.0002 (2)
C4A'	0.0118 (3)	0.0168 (3)	0.0118 (3)	0.0020 (2)	−0.0013 (2)	−0.0028 (2)
C5A'	0.0118 (3)	0.0254 (3)	0.0113 (3)	0.0006 (2)	−0.0002 (2)	−0.0034 (2)
O2A'	0.0146 (2)	0.0249 (3)	0.0141 (2)	−0.0006 (2)	0.00247 (19)	0.0001 (2)
O3A'	0.0219 (3)	0.0314 (3)	0.0126 (2)	0.0137 (3)	0.0018 (2)	0.0052 (2)
O4A'	0.0125 (2)	0.0156 (2)	0.0197 (3)	−0.00066 (17)	0.00226 (19)	−0.00222 (19)
O5A'	0.0119 (2)	0.0225 (3)	0.0100 (2)	0.00203 (18)	−0.00127 (16)	−0.00307 (18)
P1A	0.00963 (6)	0.01225 (7)	0.00883 (6)	−0.00017 (5)	−0.00009 (5)	0.00057 (5)
O1PA	0.0145 (2)	0.0185 (2)	0.0118 (2)	−0.00210 (18)	0.00259 (18)	0.00284 (18)
O2PA	0.0104 (2)	0.0176 (2)	0.0159 (2)	−0.00042 (17)	−0.00239 (17)	0.00108 (18)
O3PA	0.0152 (2)	0.0138 (2)	0.0167 (2)	0.00162 (18)	−0.00101 (19)	0.00131 (18)
C2B	0.0157 (3)	0.0112 (2)	0.0102 (2)	0.0006 (2)	−0.0007 (2)	0.00086 (19)
C4B	0.0131 (3)	0.0116 (2)	0.0118 (3)	0.00066 (19)	−0.0006 (2)	0.00035 (19)
C5B	0.0192 (3)	0.0139 (3)	0.0103 (3)	0.0034 (2)	0.0015 (2)	0.0011 (2)
C6B	0.0181 (3)	0.0143 (3)	0.0100 (3)	0.0031 (2)	0.0019 (2)	0.0022 (2)
O5B	0.0283 (3)	0.0169 (2)	0.0089 (2)	0.0031 (2)	0.0014 (2)	0.00096 (18)
N1B	0.0163 (2)	0.0114 (2)	0.0090 (2)	0.00273 (18)	0.00116 (18)	0.00142 (17)
N3B	0.0158 (2)	0.0116 (2)	0.0106 (2)	0.00206 (18)	−0.00131 (19)	0.00047 (17)
N4B	0.0200 (3)	0.0133 (2)	0.0149 (3)	0.0044 (2)	0.0020 (2)	0.00078 (19)
C1B'	0.0122 (2)	0.0114 (2)	0.0115 (2)	0.0011 (2)	0.0010 (2)	0.00074 (18)
C2B'	0.0117 (2)	0.0123 (2)	0.0118 (3)	−0.00048 (19)	−0.0002 (2)	−0.00053 (19)
C3B'	0.0147 (3)	0.0114 (3)	0.0143 (3)	0.0016 (2)	−0.0008 (2)	−0.0002 (2)
C4B'	0.0112 (2)	0.0132 (3)	0.0113 (2)	0.0007 (2)	0.0005 (2)	0.00174 (19)
C5B'	0.0117 (3)	0.0217 (3)	0.0121 (3)	−0.0003 (2)	0.0002 (2)	0.0037 (2)
O2B'	0.0128 (2)	0.0226 (3)	0.0137 (2)	−0.00245 (19)	−0.00166 (18)	−0.00235 (19)
O3B'	0.0190 (3)	0.0260 (3)	0.0148 (2)	0.0094 (2)	−0.0016 (2)	−0.0063 (2)
O4B'	0.0129 (2)	0.0121 (2)	0.0165 (2)	−0.00079 (16)	−0.00250 (18)	0.00079 (17)
O5B'	0.0120 (2)	0.0198 (2)	0.0122 (2)	0.00067 (18)	0.00173 (17)	0.00356 (18)
P1B	0.01180 (7)	0.01232 (7)	0.00905 (7)	−0.00165 (5)	0.00116 (6)	−0.00107 (5)
O1PB	0.0125 (2)	0.0193 (3)	0.0182 (3)	−0.00222 (18)	0.00464 (19)	−0.0028 (2)
O2PB	0.0195 (3)	0.0190 (2)	0.0122 (2)	−0.0049 (2)	−0.00152 (19)	−0.00349 (19)
O3PB	0.0186 (2)	0.0125 (2)	0.0143 (2)	−0.00009 (18)	0.00229 (19)	−0.00141 (17)
O1W	0.0218 (3)	0.0223 (3)	0.0199 (3)	−0.0011 (2)	−0.0025 (2)	−0.0035 (2)
O2W	0.0223 (3)	0.0260 (3)	0.0184 (3)	0.0072 (2)	−0.0015 (2)	−0.0060 (2)
O3W	0.0170 (3)	0.0582 (6)	0.0237 (4)	−0.0095 (3)	0.0007 (3)	−0.0014 (4)
O4W	0.0249 (3)	0.0188 (3)	0.0126 (2)	0.0004 (2)	0.0001 (2)	0.00103 (19)
O5W	0.0239 (3)	0.0233 (3)	0.0133 (2)	0.0017 (2)	−0.0001 (2)	−0.0010 (2)
O6W	0.0273 (3)	0.0279 (3)	0.0168 (3)	0.0022 (3)	0.0011 (3)	0.0032 (2)
O7W	0.0247 (3)	0.0191 (3)	0.0184 (3)	0.0006 (2)	−0.0036 (2)	−0.0032 (2)
O8W	0.0661 (8)	0.0248 (4)	0.0280 (4)	0.0179 (4)	0.0131 (5)	0.0044 (3)
O9W	0.0239 (3)	0.0185 (3)	0.0143 (2)	0.0018 (2)	0.0010 (2)	0.00114 (19)
O10W	0.0182 (3)	0.0280 (4)	0.0267 (4)	0.0001 (3)	−0.0026 (3)	−0.0018 (3)
Na1	0.02402 (17)	0.01783 (15)	0.01313 (14)	0.00252 (14)	0.00197 (13)	−0.00006 (11)
Na2	0.0392 (2)	0.01791 (16)	0.01406 (15)	−0.00028 (16)	0.00088 (16)	0.00039 (12)
Na3	0.01616 (15)	0.02450 (18)	0.01428 (15)	−0.00015 (13)	0.00080 (12)	0.00120 (13)
Na4	0.0261 (2)	0.0189 (2)	0.0198 (2)	0.00347 (16)	−0.00360 (17)	−0.00076 (15)

Geometric parameters (Å, º) top

C2A—O5A	1.2516 (11)	P1B—O2PB	1.5208 (7)
C2A—N3A	1.3501 (11)	O1W—H11W	0.83 (2)
C2A—N1A	1.3910 (10)	O1W—H12W	0.84 (2)
C4A—N3A	1.3367 (12)	O2W—H21W	0.72 (2)
C4A—N4A	1.3393 (11)	O2W—H22W	0.82 (2)
C4A—C5A	1.4321 (12)	O3W—H31W	0.82 (3)
C5A—C6A	1.3490 (12)	O3W—H32W	0.81 (2)
C5A—H51A	0.9500	O4W—H41W	0.836 (19)
C6A—N1A	1.3711 (11)	O4W—H42W	0.751 (19)
C6A—H61A	0.9500	O5W—H51W	0.828 (19)
N1A—C1A'	1.4626 (10)	O5W—H52W	0.870 (19)
N4A—H41A	0.8800	O6W—H61W	0.81 (2)
N4A—H42A	0.8800	O6W—H62W	0.88 (2)
C1A'—O4A'	1.4125 (10)	O7W—H71W	0.85 (2)
C1A'—C2A'	1.5312 (11)	O7W—H72W	0.78 (2)
C1A'—H11A	1.0000	O8W—H81W	0.85 (3)
C2A'—O2A'	1.4068 (10)	O8W—H82W	0.77 (3)
C2A'—C3A'	1.5379 (11)	O9W—H91W	0.765 (19)
C2A'—H21A	1.0000	O9W—H92W	0.895 (19)
C3A'—O3A'	1.4192 (11)	O10W—H13W	0.63 (2)
C3A'—C4A'	1.5415 (12)	O10W—H14W	0.90 (2)
C3A'—H31A	1.0000	O11W—O21W	0.665 (3)
C4A'—O4A'	1.4450 (10)	O11W—O31W	0.712 (7)
C4A'—C5A'	1.5150 (11)	O21W—O31W	1.305 (8)
C4A'—H43A	1.0000	O12W—O22W	0.729 (6)
C5A'—O5A'	1.4311 (10)	O22W—O1Mⁱ	1.743 (6)
C5A'—H52A	0.9900	O1M—O2M	1.031 (5)
C5A'—H53A	0.9900	O1M—C1M	1.445 (4)
O2A'—H2A'	0.89 (2)	O1M—O22Wⁱⁱ	1.743 (6)
O3A'—H3A'	0.77 (2)	O2M—O3M	0.564 (6)
O5A'—P1A	1.6250 (6)	O2M—C1M	1.403 (4)
P1A—O2PA	1.5156 (6)	O3M—C1M	1.415 (5)
P1A—O3PA	1.5216 (7)	Na1—O3PBⁱ	2.3252 (7)
P1A—O1PA	1.5236 (6)	Na1—N3Bⁱⁱⁱ	2.5201 (8)
C2B—O5B	1.2542 (10)	Na1—O1W	2.3655 (9)
C2B—N3B	1.3509 (10)	Na1—O4W	2.3824 (8)
C2B—N1B	1.3898 (10)	Na1—O7W	2.3583 (9)
C4B—N4B	1.3332 (10)	Na2—N3A^iv	2.3852 (9)
C4B—N3B	1.3423 (10)	Na2—O5A^iv	2.8008 (9)
C4B—C5B	1.4338 (11)	Na2—O3PA	2.3621 (8)
C5B—C6B	1.3489 (11)	Na2—O6W	2.3950 (10)
C5B—H51B	0.9500	Na2—O7W	2.3430 (9)
C6B—N1B	1.3684 (10)	Na3—O3B'^iv	2.3093 (8)
C6B—H61B	0.9500	Na3—O2B'^iv	2.3955 (8)
N1B—C1B'	1.4574 (10)	Na3—O1W	2.3573 (9)
N4B—H41B	0.8800	Na3—O3W	2.7470 (13)
N4B—H42B	0.8800	Na3—O4W	2.4488 (9)
C1B'—O4B'	1.4202 (10)	Na3—O5W	2.3832 (9)
C1B'—C2B'	1.5303 (10)	Na4—O1M	2.451 (3)
C1B'—H11B	1.0000	Na4—O2M	2.4351 (19)
C2B'—O2B'	1.4109 (10)	Na4—O3M	2.340 (4)
C2B'—C3B'	1.5318 (11)	Na4—O8W	2.3374 (11)
C2B'—H21B	1.0000	Na4—O9W	2.4415 (9)
C3B'—O3B'	1.4182 (11)	Na4—O10W	2.4241 (11)
C3B'—C4B'	1.5372 (11)	Na4—O11W	2.4716 (18)
C3B'—H31B	1.0000	Na4—O21W	2.394 (3)
C4B'—O4B'	1.4442 (10)	Na4—O31W	2.310 (7)
C4B'—C5B'	1.5092 (11)	Na4—O12W	2.619 (6)
C4B'—H43B	1.0000	Na4B—O1M	2.629 (6)
C5B'—O5B'	1.4352 (10)	Na4B—O2M	2.260 (5)
C5B'—H52B	0.9900	Na4B—O3M	2.359 (6)
C5B'—H53B	0.9900	Na4B—O8W	2.383 (4)
O2B'—H2B'	0.83 (2)	Na4B—O9W	2.464 (4)
O3B'—H3B'	0.79 (2)	Na4B—O11W	2.288 (5)
O5B'—P1B	1.6227 (6)	Na4B—O31W	2.400 (8)
P1B—O1PB	1.5168 (7)	Na4B—O22W	2.424 (5)
P1B—O3PB	1.5206 (6)	Na4—Na4B	0.921 (4)

O5A—C2A—N3A	120.32 (7)	O5B—C2B—N3B	121.70 (7)
O5A—C2A—N1A	120.28 (8)	O5B—C2B—N1B	118.34 (7)
N3A—C2A—N1A	119.39 (7)	N3B—C2B—N1B	119.95 (7)
N3A—C4A—N4A	117.43 (8)	N4B—C4B—N3B	118.36 (7)
N3A—C4A—C5A	121.79 (7)	N4B—C4B—C5B	119.54 (7)
N4A—C4A—C5A	120.78 (8)	N3B—C4B—C5B	122.10 (7)
C6A—C5A—C4A	116.98 (8)	C6B—C5B—C4B	117.14 (7)
C6A—C5A—H51A	121.5	C6B—C5B—H51B	121.4
C4A—C5A—H51A	121.5	C4B—C5B—H51B	121.4
C5A—C6A—N1A	121.04 (8)	C5B—C6B—N1B	120.66 (7)
C5A—C6A—H61A	119.5	C5B—C6B—H61B	119.7
N1A—C6A—H61A	119.5	N1B—C6B—H61B	119.7
C6A—N1A—C2A	120.47 (7)	C6B—N1B—C2B	120.75 (7)
C6A—N1A—C1A'	119.07 (7)	C6B—N1B—C1B'	119.16 (6)
C2A—N1A—C1A'	120.38 (7)	C2B—N1B—C1B'	119.88 (6)
C4A—N3A—C2A	120.25 (7)	C4B—N3B—C2B	119.34 (7)
C4A—N4A—H41A	120.0	C4B—N4B—H41B	120.0
C4A—N4A—H42A	120.0	C4B—N4B—H42B	120.0
H41A—N4A—H42A	120.0	H41B—N4B—H42B	120.0
O4A'—C1A'—N1A	107.59 (7)	O4B'—C1B'—N1B	107.04 (6)
O4A'—C1A'—C2A'	106.33 (6)	O4B'—C1B'—C2B'	105.86 (6)
N1A—C1A'—C2A'	114.08 (6)	N1B—C1B'—C2B'	114.63 (6)
O4A'—C1A'—H11A	109.6	O4B'—C1B'—H11B	109.7
N1A—C1A'—H11A	109.6	N1B—C1B'—H11B	109.7
C2A'—C1A'—H11A	109.6	C2B'—C1B'—H11B	109.7
O2A'—C2A'—C1A'	109.96 (6)	O2B'—C2B'—C1B'	110.74 (6)
O2A'—C2A'—C3A'	114.33 (7)	O2B'—C2B'—C3B'	113.85 (6)
C1A'—C2A'—C3A'	101.92 (6)	C1B'—C2B'—C3B'	100.33 (6)
O2A'—C2A'—H21A	110.1	O2B'—C2B'—H21B	110.5
C1A'—C2A'—H21A	110.1	C1B'—C2B'—H21B	110.5
C3A'—C2A'—H21A	110.1	C3B'—C2B'—H21B	110.5
O3A'—C3A'—C2A'	107.81 (6)	O3B'—C3B'—C2B'	106.38 (6)
O3A'—C3A'—C4A'	112.76 (7)	O3B'—C3B'—C4B'	110.55 (7)
C2A'—C3A'—C4A'	102.76 (6)	C2B'—C3B'—C4B'	102.86 (6)
O3A'—C3A'—H31A	111.1	O3B'—C3B'—H31B	112.2
C2A'—C3A'—H31A	111.1	C2B'—C3B'—H31B	112.2
C4A'—C3A'—H31A	111.1	C4B'—C3B'—H31B	112.2
O4A'—C4A'—C5A'	108.48 (7)	O4B'—C4B'—C5B'	109.11 (6)
O4A'—C4A'—C3A'	107.10 (6)	O4B'—C4B'—C3B'	106.28 (6)
C5A'—C4A'—C3A'	114.73 (7)	C5B'—C4B'—C3B'	115.67 (7)
O4A'—C4A'—H43A	108.8	O4B'—C4B'—H43B	108.5
C5A'—C4A'—H43A	108.8	C5B'—C4B'—H43B	108.5
C3A'—C4A'—H43A	108.8	C3B'—C4B'—H43B	108.5
O5A'—C5A'—C4A'	109.14 (6)	O5B'—C5B'—C4B'	109.76 (6)
O5A'—C5A'—H52A	109.9	O5B'—C5B'—H52B	109.7
C4A'—C5A'—H52A	109.9	C4B'—C5B'—H52B	109.7
O5A'—C5A'—H53A	109.9	O5B'—C5B'—H53B	109.7
C4A'—C5A'—H53A	109.9	C4B'—C5B'—H53B	109.7
H52A—C5A'—H53A	108.3	H52B—C5B'—H53B	108.2
C2A'—O2A'—H2A'	116.6 (13)	C2B'—O2B'—H2B'	109.3 (14)
C3A'—O3A'—H3A'	108.0 (16)	C3B'—O3B'—H3B'	106.9 (15)
C1A'—O4A'—C4A'	109.88 (6)	C1B'—O4B'—C4B'	109.42 (6)
C5A'—O5A'—P1A	117.73 (5)	C5B'—O5B'—P1B	116.44 (5)
O2PA—P1A—O3PA	114.01 (4)	O1PB—P1B—O3PB	113.39 (4)
O2PA—P1A—O1PA	112.15 (4)	O1PB—P1B—O2PB	112.39 (4)
O3PA—P1A—O1PA	112.35 (4)	O3PB—P1B—O2PB	112.07 (4)
O2PA—P1A—O5A'	103.35 (3)	O1PB—P1B—O5B'	103.75 (4)
O3PA—P1A—O5A'	106.57 (4)	O3PB—P1B—O5B'	106.67 (4)
O1PA—P1A—O5A'	107.64 (4)	O2PB—P1B—O5B'	107.90 (4)

N3A—C4A—C5A—C6A	−1.95 (13)	N4B—C4B—C5B—C6B	176.08 (8)
N4A—C4A—C5A—C6A	176.83 (9)	N3B—C4B—C5B—C6B	−3.08 (13)
C4A—C5A—C6A—N1A	0.84 (13)	C4B—C5B—C6B—N1B	1.56 (13)
C5A—C6A—N1A—C2A	−1.01 (13)	C5B—C6B—N1B—C2B	0.01 (13)
C5A—C6A—N1A—C1A'	−177.76 (8)	C5B—C6B—N1B—C1B'	−174.65 (8)
O5A—C2A—N1A—C6A	−179.15 (8)	O5B—C2B—N1B—C6B	179.05 (8)
N3A—C2A—N1A—C6A	2.17 (12)	N3B—C2B—N1B—C6B	−0.28 (12)
O5A—C2A—N1A—C1A'	−2.44 (12)	O5B—C2B—N1B—C1B'	−6.32 (12)
N3A—C2A—N1A—C1A'	178.88 (7)	N3B—C2B—N1B—C1B'	174.35 (7)
N4A—C4A—N3A—C2A	−175.63 (8)	N4B—C4B—N3B—C2B	−176.28 (8)
C5A—C4A—N3A—C2A	3.19 (12)	C5B—C4B—N3B—C2B	2.88 (12)
O5A—C2A—N3A—C4A	178.08 (8)	O5B—C2B—N3B—C4B	179.51 (8)
N1A—C2A—N3A—C4A	−3.25 (12)	N1B—C2B—N3B—C4B	−1.18 (12)
C6A—N1A—C1A'—O4A'	49.93 (10)	C6B—N1B—C1B'—O4B'	49.64 (9)
C2A—N1A—C1A'—O4A'	−126.83 (8)	C2B—N1B—C1B'—O4B'	−125.07 (7)
C6A—N1A—C1A'—C2A'	−67.76 (10)	C6B—N1B—C1B'—C2B'	−67.42 (10)
C2A—N1A—C1A'—C2A'	115.48 (8)	C2B—N1B—C1B'—C2B'	117.87 (8)
O4A'—C1A'—C2A'—O2A'	155.90 (6)	O4B'—C1B'—C2B'—O2B'	158.36 (6)
N1A—C1A'—C2A'—O2A'	−85.69 (8)	N1B—C1B'—C2B'—O2B'	−83.90 (8)
O4A'—C1A'—C2A'—C3A'	34.25 (8)	O4B'—C1B'—C2B'—C3B'	37.80 (7)
N1A—C1A'—C2A'—C3A'	152.67 (6)	N1B—C1B'—C2B'—C3B'	155.53 (6)
O2A'—C2A'—C3A'—O3A'	−30.53 (10)	O2B'—C2B'—C3B'—O3B'	−37.81 (9)
C1A'—C2A'—C3A'—O3A'	88.05 (8)	C1B'—C2B'—C3B'—O3B'	80.49 (7)
O2A'—C2A'—C3A'—C4A'	−149.84 (7)	O2B'—C2B'—C3B'—C4B'	−154.07 (6)
C1A'—C2A'—C3A'—C4A'	−31.26 (7)	C1B'—C2B'—C3B'—C4B'	−35.77 (7)
O3A'—C3A'—C4A'—O4A'	−96.92 (8)	O3B'—C3B'—C4B'—O4B'	−90.45 (7)
C2A'—C3A'—C4A'—O4A'	18.88 (8)	C2B'—C3B'—C4B'—O4B'	22.79 (8)
O3A'—C3A'—C4A'—C5A'	142.64 (7)	O3B'—C3B'—C4B'—C5B'	148.30 (7)
C2A'—C3A'—C4A'—C5A'	−101.57 (7)	C2B'—C3B'—C4B'—C5B'	−98.46 (7)
O4A'—C4A'—C5A'—O5A'	−69.46 (9)	O4B'—C4B'—C5B'—O5B'	−68.46 (8)
C3A'—C4A'—C5A'—O5A'	50.23 (9)	C3B'—C4B'—C5B'—O5B'	51.26 (9)
N1A—C1A'—O4A'—C4A'	−145.99 (6)	N1B—C1B'—O4B'—C4B'	−147.49 (6)
C2A'—C1A'—O4A'—C4A'	−23.38 (8)	C2B'—C1B'—O4B'—C4B'	−24.80 (8)
C5A'—C4A'—O4A'—C1A'	126.89 (7)	C5B'—C4B'—O4B'—C1B'	126.39 (7)
C3A'—C4A'—O4A'—C1A'	2.54 (8)	C3B'—C4B'—O4B'—C1B'	1.02 (8)
C4A'—C5A'—O5A'—P1A	−161.14 (6)	C4B'—C5B'—O5B'—P1B	−156.90 (6)
C5A'—O5A'—P1A—O2PA	177.17 (6)	C5B'—O5B'—P1B—O1PB	177.37 (6)
C5A'—O5A'—P1A—O3PA	56.70 (7)	C5B'—O5B'—P1B—O3PB	57.38 (7)
C5A'—O5A'—P1A—O1PA	−64.02 (7)	C5B'—O5B'—P1B—O2PB	−63.21 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41A···O3PA^v	0.88	2.18	3.0107 (11)	158
N4A—H42A···O11W	0.88	2.04	2.862 (2)	156
O2A′—H2A′···O3PB^iv	0.89 (2)	1.76 (2)	2.6480 (10)	170.5 (19)
O3A′—H3A′···O1PB^vi	0.77 (2)	1.86 (2)	2.6147 (10)	167 (2)
N4B—H41B···O3PB^vi	0.88	1.98	2.8360 (10)	163
N4B—H42B···O2W^vii	0.88	2.08	2.9224 (11)	161
O2B′—H2B′···O3PA^viii	0.83 (2)	1.83 (2)	2.6439 (9)	166 (2)
O3B′—H3B′···O2PA^v	0.79 (2)	1.82 (2)	2.5920 (9)	164 (2)
O1W—H11W···O5A^ix	0.82 (2)	2.07 (2)	2.8264 (11)	151 (2)
O1W—H12W···O6W^x	0.86 (2)	2.03 (2)	2.8412 (13)	161 (2)
O2W—H21W···O3W	0.72 (2)	2.07 (2)	2.7826 (12)	176 (2)
O2W—H22W···O2PA	0.82 (2)	1.89 (2)	2.6934 (10)	167 (2)
O3W—H31W···O1PA^xi	0.82 (2)	1.87 (2)	2.6645 (11)	165 (3)
O3W—H32W···O10Wⁱ	0.81 (2)	2.04 (2)	2.8325 (15)	169 (3)
O4W—H41W···O2PA	0.84 (2)	2.04 (2)	2.8723 (9)	171 (2)
O4W—H42W···O2PBⁱ	0.75 (2)	2.16 (2)	2.8577 (10)	156 (2)
O5W—H51W···O3A′^ix	0.83 (2)	2.07 (2)	2.8559 (10)	159 (2)
O5W—H52W···O1PA^xi	0.87 (2)	1.86 (2)	2.7257 (10)	171 (2)
O6W—H61W···O5Aⁱⁱⁱ	0.81 (2)	2.05 (2)	2.8281 (11)	162 (2)
O6W—H62W···O5B^vi	0.88 (2)	1.94 (2)	2.7887 (12)	163 (2)
O7W—H71W···O5Bⁱⁱⁱ	0.85 (2)	1.81 (2)	2.6429 (10)	166 (2)
O7W—H72W···O5W^vii	0.78 (2)	2.05 (2)	2.7938 (12)	157 (2)
O8W—H81W···O9Wⁱⁱ	0.85 (3)	1.99 (4)	2.8146 (13)	164 (3)
O8W—H82W···O2W	0.77 (3)	2.14 (4)	2.8850 (15)	163 (3)
O9W—H91W···O1PAⁱ	0.77 (2)	2.03 (2)	2.7824 (10)	169 (2)
O9W—H92W···O1PB^xi	0.90 (2)	2.03 (2)	2.8789 (10)	159 (2)
O10W—H13W···O3A′^v	0.63 (2)	2.43 (2)	2.9984 (13)	153 (3)
O10W—H14W···O2PB	0.90 (2)	1.82 (2)	2.7066 (11)	169 (2)

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

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