Crystal structure of the non-steroidal anti-inflammatory drug (NSAID) tolmetin sodium

The asymmetric unit of the title two-dimensional polymer, sodium 2-[1-methyl-5-(4-methyl­benzo­yl)-1H-pyrrol-2-yl]acetate dihydrate, Na⁺·C₁₅H₁₄NO₃⁻·2H₂O, contains two sodium cations, two organic anions and two water mol­ecules. The title compound exhibits analgesic, anti-inflammatory and anti­pyretic activities.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.191
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00464 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H3WB     ..H4WB     .       2.12 Ang.
                                                 1-x,-y,1-z  =      2_656 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.625 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595          3 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         18 Note
PLAT804_ALERT_5_G Number of ARU-Code Packing Problem(s) in PLATON           4 Info
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        32% Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   3 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
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   5 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Sodium 2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetate dihydrate

Crystal data

2Na^+·2C15H14NO3^−·4H2O	Z = 2
Mr = 630.59	F(000) = 664
Triclinic, P1	Dx = 1.394 Mg m^−3
a = 8.5404 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0144 (9) Å	Cell parameters from 1420 reflections
c = 21.6217 (19) Å	θ = 3.1–24.2°
α = 92.922 (8)°	µ = 0.13 mm^−1
β = 98.873 (7)°	T = 293 K
γ = 113.038 (9)°	Block, colourless
V = 1502.1 (3) Å^3	0.4 × 0.2 × 0.1 mm

Data collection

Rigaku Oxford Diffraction Xcalibur, Sapphire3 diffractometer	5283 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 16.1827 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −10→10
Tmin = 0.737, Tmax = 1.000	l = −25→25
11985 measured reflections

Refinement

Refinement on F^2	Primary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.191	w = 1/[σ^2(Fo^2) + (0.0844P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
5283 reflections	Δρmax = 0.38 e Å^−3
403 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Na1A	1.15418 (14)	0.48055 (14)	0.46665 (5)	0.0463 (4)
O1A	0.6328 (3)	0.4448 (3)	0.43538 (9)	0.0463 (5)
O2A	0.8756 (3)	0.4310 (3)	0.41918 (9)	0.0527 (6)
O3A	1.3144 (3)	0.5970 (3)	0.27170 (10)	0.0572 (6)
N1A	0.9595 (3)	0.5322 (3)	0.28684 (10)	0.0370 (6)
C1A	0.7367 (4)	0.4452 (3)	0.40052 (13)	0.0369 (7)
C2A	0.6907 (4)	0.4728 (4)	0.33229 (13)	0.0441 (7)
H2AA	0.568753	0.405386	0.316973	0.053*
H2AB	0.705297	0.584995	0.332112	0.053*
C3A	0.7899 (4)	0.4394 (4)	0.28655 (13)	0.0397 (7)
C4A	0.7319 (4)	0.3165 (4)	0.23764 (14)	0.0445 (7)
H4A	0.620599	0.234969	0.227154	0.053*
C5A	0.8671 (4)	0.3346 (4)	0.20653 (14)	0.0446 (7)
H5A	0.862808	0.267733	0.171513	0.053*
C6A	1.0108 (4)	0.4710 (4)	0.23717 (13)	0.0403 (7)
C7A	1.0633 (4)	0.6845 (3)	0.32769 (13)	0.0453 (7)
H7AA	1.124646	0.663236	0.364871	0.068*
H7AB	0.988702	0.733150	0.339497	0.068*
H7AC	1.144888	0.757182	0.305536	0.068*
C8A	1.1889 (4)	0.5209 (4)	0.22929 (13)	0.0392 (7)
C9A	1.2180 (4)	0.4679 (3)	0.16703 (13)	0.0399 (7)
C10A	1.1169 (4)	0.4703 (4)	0.11027 (14)	0.0457 (7)
H10A	1.026896	0.503734	0.110630	0.055*
C11A	1.1493 (4)	0.4236 (4)	0.05367 (14)	0.0488 (8)
H11A	1.079818	0.425219	0.016307	0.059*
C12A	1.2836 (4)	0.3741 (4)	0.05106 (15)	0.0455 (8)
C13A	1.3832 (4)	0.3726 (4)	0.10725 (15)	0.0508 (8)
H13A	1.472156	0.337798	0.106762	0.061*
C14A	1.3541 (4)	0.4217 (4)	0.16450 (15)	0.0478 (8)
H14A	1.426516	0.423803	0.201665	0.057*
C15A	1.3099 (5)	0.3182 (4)	−0.01169 (16)	0.0620 (9)
H15A	1.253192	0.201892	−0.019774	0.093*
H15B	1.431599	0.351811	−0.011128	0.093*
H15C	1.261676	0.365083	−0.044267	0.093*
Na1B	0.45480 (15)	0.23476 (14)	0.49496 (5)	0.0497 (4)
O1B	0.3539 (3)	0.0551 (3)	0.57285 (10)	0.0520 (6)
O2B	0.1279 (3)	0.0952 (3)	0.59464 (9)	0.0517 (6)
O3B	−0.3202 (3)	−0.0817 (3)	0.73382 (10)	0.0561 (6)
N1B	0.0316 (3)	−0.0303 (3)	0.72107 (10)	0.0392 (6)
C1B	0.2576 (4)	0.0630 (3)	0.60931 (13)	0.0372 (7)
C2B	0.2993 (4)	0.0232 (4)	0.67578 (13)	0.0469 (8)
H2BA	0.277121	−0.091173	0.673239	0.056*
H2BB	0.422204	0.084105	0.691795	0.056*
C3B	0.2033 (4)	0.0571 (4)	0.72214 (13)	0.0405 (7)
C4B	0.2635 (4)	0.1815 (4)	0.77089 (14)	0.0505 (8)
H4B	0.375714	0.261529	0.781418	0.061*
C5B	0.1287 (4)	0.1671 (4)	0.80151 (14)	0.0451 (7)
H5B	0.134436	0.234532	0.836595	0.054*
C6B	−0.0169 (4)	0.0342 (4)	0.77058 (13)	0.0414 (7)
C7B	−0.0783 (4)	−0.1782 (4)	0.67844 (14)	0.0505 (8)
H7BA	−0.140894	−0.151452	0.643088	0.076*
H7BB	−0.158712	−0.252622	0.700442	0.076*
H7BC	−0.007306	−0.227504	0.663767	0.076*
C8B	−0.1949 (4)	−0.0101 (4)	0.77748 (14)	0.0423 (7)
C9B	−0.2254 (4)	0.0398 (4)	0.83992 (13)	0.0396 (7)
C10B	−0.1236 (4)	0.0352 (4)	0.89619 (14)	0.0458 (8)
H10B	−0.034555	0.000647	0.895357	0.055*
C11B	−0.1552 (4)	0.0819 (4)	0.95293 (14)	0.0483 (8)
H11B	−0.086237	0.078848	0.990196	0.058*
C12B	−0.2879 (4)	0.1337 (4)	0.95586 (14)	0.0463 (8)
C13B	−0.3882 (4)	0.1359 (4)	0.89975 (15)	0.0505 (8)
H13B	−0.477015	0.170816	0.900353	0.061*
C14B	−0.3588 (4)	0.0871 (4)	0.84272 (15)	0.0473 (8)
H14B	−0.430573	0.086230	0.805569	0.057*
C15B	−0.3154 (4)	0.1885 (5)	1.01896 (16)	0.0610 (9)
H15D	−0.263611	0.144401	1.051608	0.091*
H15E	−0.437342	0.150939	1.018731	0.091*
H15F	−0.262690	0.304934	1.026643	0.091*
O1W	1.3788 (3)	0.5461 (3)	0.40784 (10)	0.0541 (6)
H1WA	1.363692	0.575550	0.369478	0.081*
H1WB	1.405922	0.460320	0.406558	0.081*
O2W	1.1457 (3)	0.2133 (3)	0.48044 (9)	0.0529 (6)
H2WA	1.128262	0.190038	0.518967	0.079*
H2WB	1.066822	0.127148	0.455027	0.079*
O3W	0.3857 (3)	0.0443 (3)	0.40179 (10)	0.0522 (6)
H3WA	0.383694	0.094075	0.367336	0.078*
H3WB	0.464794	0.002995	0.401246	0.078*
O4W	0.7371 (3)	0.2175 (3)	0.52238 (10)	0.0538 (6)
H4WA	0.769350	0.168269	0.493211	0.081*
H4WB	0.720981	0.138360	0.546861	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1A	0.0365 (7)	0.0608 (8)	0.0418 (7)	0.0197 (6)	0.0075 (5)	0.0091 (6)
O1A	0.0426 (12)	0.0665 (14)	0.0355 (12)	0.0258 (11)	0.0121 (9)	0.0097 (10)
O2A	0.0335 (12)	0.0802 (16)	0.0450 (13)	0.0235 (11)	0.0045 (9)	0.0188 (11)
O3A	0.0405 (13)	0.0796 (17)	0.0398 (13)	0.0148 (12)	0.0031 (10)	−0.0030 (11)
N1A	0.0369 (14)	0.0414 (13)	0.0326 (13)	0.0153 (11)	0.0071 (10)	0.0057 (10)
C1A	0.0346 (16)	0.0406 (16)	0.0358 (16)	0.0154 (13)	0.0062 (13)	0.0090 (13)
C2A	0.0430 (17)	0.0605 (19)	0.0377 (17)	0.0287 (16)	0.0091 (13)	0.0145 (14)
C3A	0.0360 (16)	0.0535 (18)	0.0337 (16)	0.0211 (14)	0.0083 (12)	0.0098 (13)
C4A	0.0381 (17)	0.0456 (18)	0.0409 (17)	0.0093 (14)	0.0030 (13)	0.0040 (14)
C5A	0.0436 (18)	0.0441 (17)	0.0417 (17)	0.0138 (15)	0.0081 (14)	0.0008 (14)
C6A	0.0422 (17)	0.0475 (17)	0.0310 (16)	0.0164 (14)	0.0105 (13)	0.0049 (13)
C7A	0.0509 (19)	0.0416 (16)	0.0377 (17)	0.0149 (15)	0.0046 (14)	−0.0007 (13)
C8A	0.0367 (16)	0.0446 (17)	0.0377 (17)	0.0158 (14)	0.0115 (13)	0.0092 (13)
C9A	0.0382 (17)	0.0432 (17)	0.0344 (16)	0.0121 (14)	0.0090 (12)	0.0016 (13)
C10A	0.0449 (18)	0.0544 (19)	0.0398 (18)	0.0215 (16)	0.0087 (14)	0.0085 (15)
C11A	0.052 (2)	0.0553 (19)	0.0364 (17)	0.0195 (17)	0.0064 (14)	0.0068 (14)
C12A	0.0412 (18)	0.0457 (18)	0.0473 (19)	0.0129 (15)	0.0147 (14)	0.0052 (14)
C13A	0.0431 (18)	0.063 (2)	0.050 (2)	0.0244 (17)	0.0117 (15)	0.0034 (16)
C14A	0.0442 (18)	0.059 (2)	0.0394 (17)	0.0204 (16)	0.0067 (14)	0.0085 (15)
C15A	0.061 (2)	0.067 (2)	0.055 (2)	0.0201 (19)	0.0208 (17)	−0.0028 (17)
Na1B	0.0459 (7)	0.0559 (8)	0.0458 (7)	0.0174 (6)	0.0125 (5)	0.0075 (6)
O1B	0.0549 (14)	0.0749 (16)	0.0407 (12)	0.0366 (12)	0.0200 (10)	0.0163 (11)
O2B	0.0505 (13)	0.0781 (16)	0.0399 (12)	0.0372 (12)	0.0140 (10)	0.0148 (11)
O3B	0.0418 (13)	0.0753 (16)	0.0411 (13)	0.0154 (12)	0.0042 (10)	−0.0022 (11)
N1B	0.0411 (14)	0.0489 (14)	0.0304 (13)	0.0200 (12)	0.0092 (10)	0.0062 (11)
C1B	0.0401 (17)	0.0379 (15)	0.0334 (16)	0.0152 (13)	0.0087 (13)	0.0024 (12)
C2B	0.0497 (19)	0.063 (2)	0.0358 (17)	0.0279 (16)	0.0147 (14)	0.0139 (15)
C3B	0.0379 (17)	0.0560 (19)	0.0327 (16)	0.0228 (15)	0.0081 (12)	0.0129 (14)
C4B	0.0376 (17)	0.061 (2)	0.0451 (19)	0.0123 (16)	0.0061 (14)	0.0113 (16)
C5B	0.0419 (17)	0.0538 (19)	0.0346 (17)	0.0148 (15)	0.0076 (13)	−0.0031 (14)
C6B	0.0379 (17)	0.0523 (18)	0.0322 (16)	0.0162 (15)	0.0061 (12)	0.0073 (13)
C7B	0.056 (2)	0.0468 (18)	0.0443 (19)	0.0197 (16)	0.0020 (15)	−0.0011 (14)
C8B	0.0414 (18)	0.0483 (18)	0.0370 (17)	0.0169 (15)	0.0093 (14)	0.0086 (14)
C9B	0.0345 (16)	0.0461 (17)	0.0373 (17)	0.0137 (14)	0.0104 (12)	0.0083 (13)
C10B	0.0464 (18)	0.0572 (19)	0.0385 (17)	0.0252 (16)	0.0092 (14)	0.0086 (14)
C11B	0.0488 (19)	0.061 (2)	0.0369 (18)	0.0231 (17)	0.0097 (14)	0.0085 (15)
C12B	0.0432 (18)	0.0501 (18)	0.0411 (18)	0.0109 (15)	0.0171 (14)	0.0046 (14)
C13B	0.0414 (18)	0.059 (2)	0.053 (2)	0.0226 (16)	0.0099 (15)	0.0015 (16)
C14B	0.0420 (18)	0.0561 (19)	0.0426 (18)	0.0192 (16)	0.0063 (14)	0.0067 (15)
C15B	0.055 (2)	0.074 (2)	0.052 (2)	0.0217 (19)	0.0174 (16)	−0.0008 (17)
O1W	0.0640 (15)	0.0639 (14)	0.0506 (13)	0.0369 (12)	0.0237 (11)	0.0180 (11)
O2W	0.0596 (14)	0.0589 (14)	0.0377 (12)	0.0211 (12)	0.0085 (10)	0.0093 (10)
O3W	0.0558 (14)	0.0637 (15)	0.0429 (12)	0.0306 (12)	0.0092 (10)	0.0048 (11)
O4W	0.0626 (15)	0.0585 (14)	0.0422 (12)	0.0260 (12)	0.0129 (10)	0.0023 (10)

Geometric parameters (Å, º)

Na1A—Na1A^i	3.314 (2)	Na1B—O1W^i	2.607 (3)
Na1A—O1A^i	2.441 (2)	Na1B—O2W^iii	2.538 (2)
Na1A—O2A	2.298 (2)	Na1B—O3W	2.417 (2)
Na1A—O2A^i	2.636 (2)	Na1B—O4W	2.460 (2)
Na1A—C1A^i	2.838 (3)	O1B—C1B	1.243 (3)
Na1A—Na1B^ii	3.9976 (16)	O2B—C1B	1.250 (3)
Na1A—Na1B^i	3.2629 (17)	O3B—C8B	1.241 (4)
Na1A—O1W	2.364 (2)	N1B—C3B	1.362 (4)
Na1A—O2W	2.417 (2)	N1B—C6B	1.385 (4)
Na1A—O4W^i	2.493 (2)	N1B—C7B	1.461 (4)
O1A—C1A	1.249 (3)	C1B—C2B	1.522 (4)
O1A—Na1B	2.481 (2)	C2B—H2BA	0.9700
O2A—C1A	1.250 (3)	C2B—H2BB	0.9700
O3A—C8A	1.232 (3)	C2B—C3B	1.479 (4)
N1A—C3A	1.359 (4)	C3B—C4B	1.376 (4)
N1A—C6A	1.387 (3)	C4B—H4B	0.9300
N1A—C7A	1.461 (4)	C4B—C5B	1.382 (4)
C1A—C2A	1.526 (4)	C5B—H5B	0.9300
C2A—H2AA	0.9700	C5B—C6B	1.387 (4)
C2A—H2AB	0.9700	C6B—C8B	1.446 (4)
C2A—C3A	1.488 (4)	C7B—H7BA	0.9600
C3A—C4A	1.371 (4)	C7B—H7BB	0.9600
C4A—H4A	0.9300	C7B—H7BC	0.9600
C4A—C5A	1.384 (4)	C8B—C9B	1.494 (4)
C5A—H5A	0.9300	C9B—C10B	1.395 (4)
C5A—C6A	1.394 (4)	C9B—C14B	1.371 (4)
C6A—C8A	1.448 (4)	C10B—H10B	0.9300
C7A—H7AA	0.9600	C10B—C11B	1.376 (4)
C7A—H7AB	0.9600	C11B—H11B	0.9300
C7A—H7AC	0.9600	C11B—C12B	1.393 (4)
C8A—C9A	1.494 (4)	C12B—C13B	1.379 (4)
C9A—C10A	1.394 (4)	C12B—C15B	1.510 (4)
C9A—C14A	1.387 (4)	C13B—H13B	0.9300
C10A—H10A	0.9300	C13B—C14B	1.380 (4)
C10A—C11A	1.376 (4)	C14B—H14B	0.9300
C11A—H11A	0.9300	C15B—H15D	0.9600
C11A—C12A	1.391 (4)	C15B—H15E	0.9600
C12A—C13A	1.375 (4)	C15B—H15F	0.9600
C12A—C15A	1.503 (4)	O1W—H1WA	0.8897
C13A—H13A	0.9300	O1W—H1WB	0.8899
C13A—C14A	1.384 (4)	O2W—H2WA	0.8899
C14A—H14A	0.9300	O2W—H2WB	0.8899
C15A—H15A	0.9600	O3W—H3WA	0.8905
C15A—H15B	0.9600	O3W—H3WB	0.8905
C15A—H15C	0.9600	O4W—H4WA	0.8897
Na1B—O1B	2.416 (2)	O4W—H4WB	0.8902
Na1A^i—Na1A—Na1B^ii	135.58 (5)	H15A—C15A—H15C	109.5
O1A^i—Na1A—Na1A^i	94.89 (7)	H15B—C15A—H15C	109.5
O1A^i—Na1A—O2A^i	51.31 (6)	Na1A^i—Na1B—Na1A^iii	103.67 (4)
O1A^i—Na1A—C1A^i	26.00 (7)	O1A—Na1B—Na1A^i	47.95 (5)
O1A^i—Na1A—Na1B^i	49.01 (5)	O1A—Na1B—Na1A^iii	81.27 (6)
O1A^i—Na1A—Na1B^ii	61.96 (6)	O1A—Na1B—O1W^i	83.94 (8)
O1A^i—Na1A—O4W^i	78.93 (8)	O1A—Na1B—O2W^iii	111.77 (8)
O2A^i—Na1A—Na1A^i	43.62 (5)	O1B—Na1B—Na1A^i	116.87 (7)
O2A—Na1A—Na1A^i	52.29 (6)	O1B—Na1B—Na1A^iii	107.75 (6)
O2A—Na1A—O1A^i	147.11 (9)	O1B—Na1B—O1A	164.64 (8)
O2A—Na1A—O2A^i	95.91 (8)	O1B—Na1B—O1W^i	84.57 (8)
O2A^i—Na1A—C1A^i	26.07 (7)	O1B—Na1B—O2W^iii	81.05 (7)
O2A—Na1A—C1A^i	121.17 (9)	O1B—Na1B—O3W	101.75 (9)
O2A^i—Na1A—Na1B^ii	104.45 (6)	O1B—Na1B—O4W	88.42 (8)
O2A—Na1A—Na1B^i	142.94 (8)	O1W^i—Na1B—Na1A^i	45.82 (5)
O2A^i—Na1A—Na1B^i	84.23 (6)	O1W^i—Na1B—Na1A^iii	84.57 (6)
O2A—Na1A—Na1B^ii	138.04 (8)	O2W^iii—Na1B—Na1A^iii	35.20 (5)
O2A—Na1A—O1W	121.00 (9)	O2W^iii—Na1B—Na1A^i	137.63 (7)
O2A—Na1A—O2W	103.90 (9)	O2W^iii—Na1B—O1W^i	104.60 (8)
O2A—Na1A—O4W^i	95.91 (8)	O3W—Na1B—Na1A^iii	107.78 (6)
C1A^i—Na1A—Na1A^i	69.18 (7)	O3W—Na1B—Na1A^i	118.49 (7)
C1A^i—Na1A—Na1B^ii	80.46 (6)	O3W—Na1B—O1A	86.73 (8)
C1A^i—Na1A—Na1B^i	68.45 (6)	O3W—Na1B—O1W^i	163.22 (8)
Na1B^i—Na1A—Na1A^i	118.26 (6)	O3W—Na1B—O2W^iii	91.80 (8)
Na1B^i—Na1A—Na1B^ii	76.33 (4)	O3W—Na1B—O4W	89.29 (8)
O1W—Na1A—Na1A^i	158.68 (9)	O4W—Na1B—Na1A^iii	152.90 (7)
O1W—Na1A—O1A^i	90.21 (8)	O4W—Na1B—Na1A^i	49.23 (6)
O1W—Na1A—O2A^i	136.23 (9)	O4W—Na1B—O1A	78.81 (8)
O1W—Na1A—C1A^i	115.58 (9)	O4W—Na1B—O1W^i	75.24 (8)
O1W—Na1A—Na1B^i	52.29 (6)	O4W—Na1B—O2W^iii	169.41 (8)
O1W—Na1A—Na1B^ii	64.50 (6)	C1B—O1B—Na1B	126.86 (19)
O1W—Na1A—O2W	93.84 (8)	C3B—N1B—C6B	109.0 (2)
O1W—Na1A—O4W^i	79.14 (8)	C3B—N1B—C7B	125.0 (2)
O2W—Na1A—Na1A^i	107.35 (7)	C6B—N1B—C7B	125.7 (2)
O2W—Na1A—O1A^i	82.17 (8)	O1B—C1B—O2B	125.0 (3)
O2W—Na1A—O2A^i	99.52 (8)	O1B—C1B—C2B	116.3 (3)
O2W—Na1A—C1A^i	86.62 (8)	O2B—C1B—C2B	118.7 (2)
O2W—Na1A—Na1B^i	112.65 (7)	C1B—C2B—H2BA	108.2
O2W—Na1A—Na1B^ii	37.26 (6)	C1B—C2B—H2BB	108.2
O2W—Na1A—O4W^i	159.77 (8)	H2BA—C2B—H2BB	107.3
O4W^i—Na1A—Na1A^i	81.55 (7)	C3B—C2B—C1B	116.5 (2)
O4W^i—Na1A—O2A^i	74.06 (8)	C3B—C2B—H2BA	108.2
O4W^i—Na1A—C1A^i	79.57 (8)	C3B—C2B—H2BB	108.2
O4W^i—Na1A—Na1B^i	48.35 (6)	N1B—C3B—C2B	123.9 (3)
O4W^i—Na1A—Na1B^ii	124.68 (6)	N1B—C3B—C4B	107.9 (2)
Na1A^i—O1A—Na1B	83.04 (7)	C4B—C3B—C2B	128.1 (3)
C1A—O1A—Na1A^i	95.05 (17)	C3B—C4B—H4B	125.9
C1A—O1A—Na1B	132.45 (19)	C3B—C4B—C5B	108.2 (3)
Na1A—O2A—Na1A^i	84.09 (8)	C5B—C4B—H4B	125.9
C1A—O2A—Na1A^i	86.05 (17)	C4B—C5B—H5B	126.1
C1A—O2A—Na1A	163.4 (2)	C4B—C5B—C6B	107.8 (3)
C3A—N1A—C6A	109.3 (2)	C6B—C5B—H5B	126.1
C3A—N1A—C7A	124.8 (2)	N1B—C6B—C5B	107.0 (3)
C6A—N1A—C7A	125.4 (2)	N1B—C6B—C8B	123.9 (3)
O1A—C1A—Na1A^i	58.95 (14)	C5B—C6B—C8B	127.8 (3)
O1A—C1A—O2A	123.8 (3)	N1B—C7B—H7BA	109.5
O1A—C1A—C2A	116.3 (2)	N1B—C7B—H7BB	109.5
O2A—C1A—Na1A^i	67.89 (15)	N1B—C7B—H7BC	109.5
O2A—C1A—C2A	119.8 (2)	H7BA—C7B—H7BB	109.5
C2A—C1A—Na1A^i	158.3 (2)	H7BA—C7B—H7BC	109.5
C1A—C2A—H2AA	107.9	H7BB—C7B—H7BC	109.5
C1A—C2A—H2AB	107.9	O3B—C8B—C6B	123.2 (3)
H2AA—C2A—H2AB	107.2	O3B—C8B—C9B	119.5 (3)
C3A—C2A—C1A	117.4 (2)	C6B—C8B—C9B	117.3 (3)
C3A—C2A—H2AA	107.9	C10B—C9B—C8B	121.3 (3)
C3A—C2A—H2AB	107.9	C14B—C9B—C8B	120.0 (3)
N1A—C3A—C2A	123.8 (3)	C14B—C9B—C10B	118.7 (3)
N1A—C3A—C4A	108.1 (2)	C9B—C10B—H10B	120.1
C4A—C3A—C2A	128.1 (3)	C11B—C10B—C9B	119.9 (3)
C3A—C4A—H4A	125.8	C11B—C10B—H10B	120.1
C3A—C4A—C5A	108.4 (3)	C10B—C11B—H11B	119.2
C5A—C4A—H4A	125.8	C10B—C11B—C12B	121.5 (3)
C4A—C5A—H5A	126.2	C12B—C11B—H11B	119.2
C4A—C5A—C6A	107.6 (3)	C11B—C12B—C15B	120.0 (3)
C6A—C5A—H5A	126.2	C13B—C12B—C11B	117.7 (3)
N1A—C6A—C5A	106.6 (3)	C13B—C12B—C15B	122.3 (3)
N1A—C6A—C8A	124.4 (3)	C12B—C13B—H13B	119.5
C5A—C6A—C8A	127.6 (3)	C12B—C13B—C14B	121.1 (3)
N1A—C7A—H7AA	109.5	C14B—C13B—H13B	119.5
N1A—C7A—H7AB	109.5	C9B—C14B—C13B	121.1 (3)
N1A—C7A—H7AC	109.5	C9B—C14B—H14B	119.5
H7AA—C7A—H7AB	109.5	C13B—C14B—H14B	119.5
H7AA—C7A—H7AC	109.5	C12B—C15B—H15D	109.5
H7AB—C7A—H7AC	109.5	C12B—C15B—H15E	109.5
O3A—C8A—C6A	123.4 (3)	C12B—C15B—H15F	109.5
O3A—C8A—C9A	119.5 (3)	H15D—C15B—H15E	109.5
C6A—C8A—C9A	117.0 (3)	H15D—C15B—H15F	109.5
C10A—C9A—C8A	122.0 (3)	H15E—C15B—H15F	109.5
C14A—C9A—C8A	119.9 (3)	Na1A—O1W—Na1B^i	81.89 (7)
C14A—C9A—C10A	118.0 (3)	Na1A—O1W—H1WA	120.2
C9A—C10A—H10A	119.7	Na1A—O1W—H1WB	105.3
C11A—C10A—C9A	120.5 (3)	Na1B^i—O1W—H1WA	120.3
C11A—C10A—H10A	119.7	Na1B^i—O1W—H1WB	115.2
C10A—C11A—H11A	119.2	H1WA—O1W—H1WB	110.6
C10A—C11A—C12A	121.5 (3)	Na1A—O2W—Na1B^ii	107.54 (9)
C12A—C11A—H11A	119.2	Na1A—O2W—H2WA	110.1
C11A—C12A—C15A	119.7 (3)	Na1A—O2W—H2WB	119.8
C13A—C12A—C11A	117.6 (3)	Na1B^ii—O2W—H2WA	97.1
C13A—C12A—C15A	122.7 (3)	Na1B^ii—O2W—H2WB	115.5
C12A—C13A—H13A	119.2	H2WA—O2W—H2WB	104.2
C12A—C13A—C14A	121.5 (3)	Na1B—O3W—H3WA	110.1
C14A—C13A—H13A	119.2	Na1B—O3W—H3WB	111.9
C9A—C14A—H14A	119.7	H3WA—O3W—H3WB	106.7
C13A—C14A—C9A	120.7 (3)	Na1A^i—O4W—H4WA	118.6
C13A—C14A—H14A	119.7	Na1A^i—O4W—H4WB	139.0
C12A—C15A—H15A	109.5	Na1B—O4W—Na1A^i	82.42 (7)
C12A—C15A—H15B	109.5	Na1B—O4W—H4WA	117.6
C12A—C15A—H15C	109.5	Na1B—O4W—H4WB	105.9
H15A—C15A—H15B	109.5	H4WA—O4W—H4WB	93.5
Na1A^i—O1A—C1A—O2A	21.2 (3)	C15A—C12A—C13A—C14A	−178.7 (3)
Na1A^i—O1A—C1A—C2A	−155.9 (2)	Na1B—O1A—C1A—Na1A^i	−85.19 (19)
Na1A—O2A—C1A—Na1A^i	−53.7 (6)	Na1B—O1A—C1A—O2A	−64.0 (4)
Na1A^i—O2A—C1A—O1A	−19.5 (3)	Na1B—O1A—C1A—C2A	119.0 (2)
Na1A—O2A—C1A—O1A	−73.2 (8)	Na1B—O1B—C1B—O2B	40.8 (4)
Na1A^i—O2A—C1A—C2A	157.4 (2)	Na1B—O1B—C1B—C2B	−141.7 (2)
Na1A—O2A—C1A—C2A	103.7 (7)	O1B—C1B—C2B—C3B	170.7 (3)
Na1A^i—C1A—C2A—C3A	120.9 (5)	O2B—C1B—C2B—C3B	−11.7 (4)
O1A—C1A—C2A—C3A	−167.4 (3)	O3B—C8B—C9B—C10B	144.1 (3)
O2A—C1A—C2A—C3A	15.5 (4)	O3B—C8B—C9B—C14B	−34.1 (4)
O3A—C8A—C9A—C10A	−142.0 (3)	N1B—C3B—C4B—C5B	2.0 (3)
O3A—C8A—C9A—C14A	34.9 (4)	N1B—C6B—C8B—O3B	−16.1 (5)
N1A—C3A—C4A—C5A	−0.8 (3)	N1B—C6B—C8B—C9B	166.3 (3)
N1A—C6A—C8A—O3A	15.4 (5)	C1B—C2B—C3B—N1B	71.0 (4)
N1A—C6A—C8A—C9A	−168.0 (3)	C1B—C2B—C3B—C4B	−105.8 (3)
C1A—C2A—C3A—N1A	−70.1 (4)	C2B—C3B—C4B—C5B	179.2 (3)
C1A—C2A—C3A—C4A	110.7 (3)	C3B—N1B—C6B—C5B	1.6 (3)
C2A—C3A—C4A—C5A	178.5 (3)	C3B—N1B—C6B—C8B	169.0 (3)
C3A—N1A—C6A—C5A	−1.0 (3)	C3B—C4B—C5B—C6B	−1.1 (4)
C3A—N1A—C6A—C8A	−168.7 (3)	C4B—C5B—C6B—N1B	−0.3 (3)
C3A—C4A—C5A—C6A	0.2 (3)	C4B—C5B—C6B—C8B	−167.0 (3)
C4A—C5A—C6A—N1A	0.5 (3)	C5B—C6B—C8B—O3B	148.6 (3)
C4A—C5A—C6A—C8A	167.7 (3)	C5B—C6B—C8B—C9B	−29.0 (4)
C5A—C6A—C8A—O3A	−149.7 (3)	C6B—N1B—C3B—C2B	−179.5 (3)
C5A—C6A—C8A—C9A	26.9 (4)	C6B—N1B—C3B—C4B	−2.2 (3)
C6A—N1A—C3A—C2A	−178.3 (2)	C6B—C8B—C9B—C10B	−38.2 (4)
C6A—N1A—C3A—C4A	1.1 (3)	C6B—C8B—C9B—C14B	143.6 (3)
C6A—C8A—C9A—C10A	41.3 (4)	C7B—N1B—C3B—C2B	6.3 (4)
C6A—C8A—C9A—C14A	−141.8 (3)	C7B—N1B—C3B—C4B	−176.4 (3)
C7A—N1A—C3A—C2A	−6.0 (4)	C7B—N1B—C6B—C5B	175.7 (3)
C7A—N1A—C3A—C4A	173.4 (2)	C7B—N1B—C6B—C8B	−16.9 (4)
C7A—N1A—C6A—C5A	−173.2 (2)	C8B—C9B—C10B—C11B	−180.0 (3)
C7A—N1A—C6A—C8A	19.0 (4)	C8B—C9B—C14B—C13B	−179.1 (3)
C8A—C9A—C10A—C11A	178.7 (3)	C9B—C10B—C11B—C12B	0.3 (5)
C8A—C9A—C14A—C13A	−179.9 (3)	C10B—C9B—C14B—C13B	2.7 (5)
C9A—C10A—C11A—C12A	−0.5 (5)	C10B—C11B—C12B—C13B	0.3 (5)
C10A—C9A—C14A—C13A	−2.8 (5)	C10B—C11B—C12B—C15B	−178.3 (3)
C10A—C11A—C12A—C13A	0.3 (5)	C11B—C12B—C13B—C14B	0.6 (5)
C10A—C11A—C12A—C15A	177.7 (3)	C12B—C13B—C14B—C9B	−2.1 (5)
C11A—C12A—C13A—C14A	−1.3 (5)	C14B—C9B—C10B—C11B	−1.8 (5)
C12A—C13A—C14A—C9A	2.7 (5)	C15B—C12B—C13B—C14B	179.1 (3)
C14A—C9A—C10A—C11A	1.8 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3A	0.89	2.12	3.002 (3)	169
O1W—H1WB···O1A^ii	0.89	2.00	2.665 (4)	130
O2W—H2WA···O2B^ii	0.89	1.88	2.741 (3)	161
O2W—H2WB···O2B^iv	0.89	2.13	3.019 (3)	172
O3W—H3WA···O3B^v	0.89	2.16	2.961 (3)	150
O3W—H3WB···O1B^iv	0.89	1.84	2.699 (4)	161
O4W—H4WA···O1B^iv	0.89	2.19	2.894 (3)	136
O4W—H4WB···O3W^iv	0.89	2.02	2.889 (3)	163

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