The complex of flunixin and meglumine

Cao, X.-J.; Sun, C.-R..; Pan, Y.-J.

doi:10.1107/S1600536803019470

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The complex of flunixin and meglumine

X.-J. Cao, C.-R. Sun and Y.-J. Pan

The flunixin–meglumine complex [(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxy-N-methyl–1-hexanaminium 2-[2-methyl-3-(trifluoromethyl)anilino]nicotinate], C₇H₁₈NO₅⁺·C₁₄H₁₀F₃N₂O₂⁻, is a non-steroidal anti-inflammatory drug (NSAID) and a non-narcotic analgesic drug with antipyretic activities. In its crystal structure, the meglumine cations are linked through O—H

O and N—H

O hydrogen bonds to form layers parallel to the ab plane. The flunixin anions are arranged between the two cationic layers and are linked to the cations through O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019470/ci6259sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019470/ci6259Isup2.hkl Contains datablock I

CCDC reference: 225713

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.085
Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C13
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N3
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
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           29.00
           From the CIF: _reflns_number_total               3269
           Count of symmetry unique reflns         3269
           Completeness (_total/calc)            100.00%
           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
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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 top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxy-N-methyl-1-hexanaminium-2- [2-methyl-3-(trifluoromethyl)anilino]nicotinate top

Crystal data top

C₇H₁₈NO₅⁺·C₁₄H₁₀F₃N₂O₂⁻	F(000) = 516
M_r = 491.46	D_x = 1.438 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 28 reflections
a = 9.910 (1) Å	θ = 3.7–14.8°
b = 6.914 (1) Å	µ = 0.12 mm⁻¹
c = 16.578 (2) Å	T = 296 K
β = 91.86 (1)°	Prism, colourless
V = 1135.2 (2) Å³	0.52 × 0.52 × 0.38 mm
Z = 2

Data collection top

Siemens P4 diffractometer	R_int = 0.014
Radiation source: normal-focus sealed tube	θ_max = 29.0°, θ_min = 1.2°
Graphite monochromator	h = −12→13
ω scan	k = −8→9
6316 measured reflections	l = −22→22
3269 independent reflections	3 standard reflections every 97 reflections
2594 reflections with I > 2σ(I)	intensity decay: 1.9%

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0534P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3269 reflections	Δρ_max = 0.20 e Å⁻³
327 parameters	Δρ_min = −0.17 e Å⁻³
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (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. 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

	x	y	z	U_iso*/U_eq
F1	0.88860 (19)	−0.0075 (4)	0.82433 (11)	0.0986 (7)
F2	0.98091 (17)	0.1020 (4)	0.93284 (13)	0.1025 (7)
F3	0.8559 (2)	−0.1486 (3)	0.93711 (13)	0.1013 (7)
O1	0.19090 (13)	0.1331 (2)	0.62123 (8)	0.0432 (3)
O2	0.31828 (15)	−0.0150 (2)	0.71467 (8)	0.0489 (4)
O3	0.15186 (12)	0.1747 (2)	0.40978 (9)	0.0422 (3)
H3O	0.0983	0.1016	0.4309	0.051*
O4	0.05526 (12)	0.4356 (2)	0.53848 (8)	0.0382 (3)
H4O	0.0988	0.3482	0.5603	0.046*
O5	0.33528 (14)	0.5779 (2)	0.41394 (8)	0.0383 (3)
H5O	0.3874	0.4935	0.3996	0.046*
O6	0.27968 (14)	0.8519 (2)	0.51769 (8)	0.0365 (3)
H6O	0.2536	0.9256	0.5527	0.044*
O7	0.49468 (13)	0.8112 (2)	0.62824 (9)	0.0408 (3)
H7O	0.4296	0.8536	0.6519	0.049*
N1	0.2587 (2)	0.4629 (4)	0.87041 (13)	0.0813 (8)
N2	0.39371 (19)	0.1974 (3)	0.84289 (10)	0.0468 (4)
N3	0.63483 (15)	0.4518 (3)	0.64228 (9)	0.0322 (3)
C1	0.1518 (4)	0.5734 (7)	0.85174 (19)	0.1049 (15)
H1	0.1350	0.6789	0.8847	0.126*
C2	0.0651 (3)	0.5410 (5)	0.78684 (17)	0.0808 (10)
H2	−0.0100	0.6192	0.7771	0.097*
C3	0.0936 (2)	0.3887 (4)	0.73691 (13)	0.0530 (6)
H3	0.0371	0.3636	0.6922	0.064*
C4	0.20487 (18)	0.2722 (3)	0.75215 (11)	0.0381 (4)
C5	0.2847 (2)	0.3135 (4)	0.82266 (12)	0.0464 (5)
C6	0.5133 (2)	0.2385 (3)	0.88682 (10)	0.0399 (5)
C7	0.5324 (2)	0.4071 (4)	0.93148 (12)	0.0509 (6)
H7	0.4608	0.4918	0.9385	0.061*
C8	0.6589 (3)	0.4485 (4)	0.96556 (14)	0.0581 (6)
H8	0.6712	0.5612	0.9955	0.070*
C9	0.7655 (2)	0.3266 (4)	0.95586 (13)	0.0556 (6)
H9	0.8507	0.3593	0.9767	0.067*
C10	0.7461 (2)	0.1537 (4)	0.91470 (12)	0.0495 (5)
C11	0.6186 (2)	0.1030 (3)	0.88144 (11)	0.0449 (5)
C12	0.24000 (17)	0.1186 (3)	0.69172 (10)	0.0338 (4)
C13	0.8669 (3)	0.0259 (5)	0.90239 (18)	0.0684 (8)
C14	0.5928 (3)	−0.0870 (4)	0.83979 (17)	0.0670 (7)
H14A	0.6650	−0.1750	0.8531	0.080*
H14B	0.5877	−0.0672	0.7824	0.080*
H14C	0.5091	−0.1402	0.8572	0.080*
C15	0.0902 (2)	0.3598 (3)	0.39744 (12)	0.0414 (4)
H15A	−0.0067	0.3435	0.3908	0.050*
H15B	0.1229	0.4166	0.3483	0.050*
C16	0.12052 (17)	0.4959 (3)	0.46768 (10)	0.0322 (4)
H16	0.0850	0.6236	0.4527	0.039*
C17	0.27170 (17)	0.5175 (3)	0.48546 (10)	0.0289 (4)
H17	0.3087	0.3917	0.5022	0.035*
C18	0.30405 (16)	0.6662 (3)	0.55185 (10)	0.0291 (4)
H18	0.2454	0.6456	0.5975	0.035*
C19	0.45376 (15)	0.6513 (3)	0.58031 (10)	0.0292 (3)
H19	0.5092	0.6488	0.5324	0.035*
C20	0.48473 (17)	0.4710 (3)	0.62930 (13)	0.0380 (4)
H20A	0.4419	0.4791	0.6810	0.046*
H20B	0.4494	0.3582	0.6010	0.046*
C21	0.6783 (3)	0.3969 (7)	0.72321 (13)	0.0794 (11)
H21A	0.6338	0.2794	0.7380	0.095*
H21B	0.6558	0.4978	0.7602	0.095*
H21C	0.7742	0.3770	0.7251	0.095*
H2N	0.400 (2)	0.096 (2)	0.8143 (11)	0.036 (6)*
H3NA	0.677 (2)	0.554 (3)	0.6272 (14)	0.051 (7)*
H3NB	0.665 (3)	0.371 (4)	0.6072 (14)	0.063 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0841 (11)	0.1262 (19)	0.0852 (11)	0.0382 (13)	−0.0006 (9)	−0.0232 (13)
F2	0.0589 (9)	0.1076 (17)	0.1386 (16)	0.0131 (11)	−0.0342 (10)	−0.0239 (15)
F3	0.0974 (13)	0.0738 (13)	0.1303 (16)	0.0257 (11)	−0.0344 (12)	0.0168 (13)
O1	0.0484 (7)	0.0431 (8)	0.0375 (6)	0.0065 (7)	−0.0048 (5)	−0.0081 (7)
O2	0.0525 (8)	0.0485 (9)	0.0451 (7)	0.0137 (8)	−0.0053 (6)	−0.0103 (7)
O3	0.0333 (6)	0.0309 (7)	0.0628 (9)	−0.0016 (6)	0.0092 (6)	−0.0089 (7)
O4	0.0278 (6)	0.0345 (7)	0.0526 (7)	0.0027 (6)	0.0061 (5)	0.0004 (6)
O5	0.0445 (7)	0.0283 (7)	0.0430 (7)	0.0037 (6)	0.0143 (6)	0.0006 (6)
O6	0.0477 (7)	0.0244 (6)	0.0374 (7)	0.0093 (6)	0.0023 (6)	−0.0018 (5)
O7	0.0299 (6)	0.0359 (7)	0.0571 (8)	−0.0073 (6)	0.0064 (6)	−0.0133 (7)
N1	0.0825 (15)	0.097 (2)	0.0626 (12)	0.0427 (16)	−0.0252 (11)	−0.0438 (14)
N2	0.0511 (10)	0.0479 (11)	0.0408 (9)	0.0087 (9)	−0.0081 (8)	−0.0106 (8)
N3	0.0290 (7)	0.0347 (8)	0.0328 (7)	−0.0002 (7)	−0.0007 (6)	0.0003 (7)
C1	0.104 (2)	0.125 (3)	0.0840 (19)	0.067 (2)	−0.0283 (18)	−0.068 (2)
C2	0.0725 (17)	0.098 (2)	0.0710 (16)	0.0497 (18)	−0.0151 (13)	−0.0356 (17)
C3	0.0486 (11)	0.0694 (16)	0.0410 (10)	0.0161 (12)	0.0004 (9)	−0.0126 (11)
C4	0.0349 (9)	0.0453 (12)	0.0344 (8)	0.0045 (9)	0.0052 (7)	−0.0047 (9)
C5	0.0475 (11)	0.0531 (13)	0.0386 (10)	0.0098 (10)	0.0011 (8)	−0.0107 (10)
C6	0.0470 (11)	0.0437 (11)	0.0288 (9)	−0.0003 (9)	−0.0020 (8)	0.0021 (9)
C7	0.0566 (13)	0.0544 (15)	0.0417 (10)	0.0031 (11)	−0.0007 (10)	−0.0084 (10)
C8	0.0681 (14)	0.0576 (15)	0.0482 (11)	−0.0058 (13)	−0.0056 (10)	−0.0138 (12)
C9	0.0557 (13)	0.0616 (16)	0.0485 (12)	−0.0065 (13)	−0.0129 (10)	−0.0008 (12)
C10	0.0538 (12)	0.0528 (14)	0.0411 (10)	0.0059 (12)	−0.0116 (9)	0.0069 (11)
C11	0.0554 (12)	0.0421 (12)	0.0365 (9)	0.0056 (10)	−0.0103 (9)	0.0030 (9)
C12	0.0280 (7)	0.0357 (10)	0.0379 (9)	−0.0028 (8)	0.0038 (7)	−0.0056 (8)
C13	0.0586 (15)	0.0706 (19)	0.0746 (17)	0.0132 (14)	−0.0191 (12)	−0.0012 (16)
C14	0.0720 (16)	0.0463 (15)	0.0806 (17)	0.0150 (13)	−0.0304 (14)	−0.0109 (13)
C15	0.0377 (9)	0.0387 (11)	0.0471 (10)	0.0012 (9)	−0.0074 (8)	−0.0042 (9)
C16	0.0293 (8)	0.0259 (9)	0.0412 (9)	0.0034 (7)	−0.0014 (7)	0.0013 (8)
C17	0.0271 (8)	0.0245 (8)	0.0351 (8)	0.0025 (7)	0.0026 (6)	0.0012 (7)
C18	0.0268 (7)	0.0246 (9)	0.0360 (8)	0.0020 (7)	0.0031 (6)	−0.0006 (7)
C19	0.0252 (7)	0.0265 (9)	0.0361 (8)	−0.0030 (7)	0.0042 (6)	0.0001 (8)
C20	0.0245 (8)	0.0382 (11)	0.0511 (11)	−0.0048 (8)	−0.0006 (8)	0.0093 (9)
C21	0.0528 (13)	0.141 (3)	0.0435 (11)	0.0038 (18)	−0.0087 (10)	0.0229 (17)

Geometric parameters (Å, º) top

F1—C13	1.339 (3)	C4—C12	1.508 (3)
F2—C13	1.331 (3)	C6—C7	1.391 (3)
F3—C13	1.343 (4)	C6—C11	1.408 (3)
O1—C12	1.255 (2)	C7—C8	1.388 (3)
O2—C12	1.257 (2)	C7—H7	0.93
O3—C15	1.430 (3)	C8—C9	1.365 (4)
O3—H3O	0.82	C8—H8	0.93
O4—C16	1.421 (2)	C9—C10	1.387 (4)
O4—H4O	0.82	C9—H9	0.93
O5—C17	1.423 (2)	C10—C11	1.406 (3)
O5—H5O	0.82	C10—C13	1.507 (4)
O6—C18	1.420 (2)	C11—C14	1.502 (4)
O6—H6O	0.82	C14—H14A	0.96
O7—C19	1.413 (2)	C14—H14B	0.96
O7—H7O	0.82	C14—H14C	0.96
N1—C5	1.332 (3)	C15—C16	1.520 (3)
N1—C1	1.334 (4)	C15—H15A	0.97
N2—C5	1.378 (3)	C15—H15B	0.97
N2—C6	1.399 (3)	C16—C17	1.525 (2)
N2—H2N	0.85 (2)	C16—H16	0.98
N3—C21	1.446 (3)	C17—C18	1.533 (2)
N3—C20	1.502 (2)	C17—H17	0.98
N3—H3NA	0.86 (2)	C18—C19	1.546 (2)
N3—H3NB	0.87 (3)	C18—H18	0.98
C1—C2	1.374 (4)	C19—C20	1.514 (3)
C1—H1	0.93	C19—H19	0.98
C2—C3	1.375 (4)	C20—H20A	0.97
C2—H2	0.93	C20—H20B	0.97
C3—C4	1.382 (3)	C21—H21A	0.96
C3—H3	0.93	C21—H21B	0.96
C4—C5	1.419 (3)	C21—H21C	0.96

C15—O3—H3O	109.5	F1—C13—F3	106.1 (3)
C16—O4—H4O	109.5	F2—C13—C10	112.7 (3)
C17—O5—H5O	109.5	F1—C13—C10	112.7 (2)
C18—O6—H6O	109.5	F3—C13—C10	113.1 (3)
C19—O7—H7O	109.5	C11—C14—H14A	109.5
C5—N1—C1	118.3 (2)	C11—C14—H14B	109.5
C5—N2—C6	130.7 (2)	H14A—C14—H14B	109.5
C5—N2—H2N	114.7 (15)	C11—C14—H14C	109.5
C6—N2—H2N	112.3 (15)	H14A—C14—H14C	109.5
C21—N3—C20	114.83 (16)	H14B—C14—H14C	109.5
C21—N3—H3NA	110.7 (16)	O3—C15—C16	111.81 (15)
C20—N3—H3NA	111.7 (17)	O3—C15—H15A	109.3
C21—N3—H3NB	110.7 (19)	C16—C15—H15A	109.3
C20—N3—H3NB	108.5 (19)	O3—C15—H15B	109.3
H3NA—N3—H3NB	99 (2)	C16—C15—H15B	109.3
N1—C1—C2	124.1 (3)	H15A—C15—H15B	107.9
N1—C1—H1	118.0	O4—C16—C15	111.55 (16)
C2—C1—H1	118.0	O4—C16—C17	109.86 (14)
C1—C2—C3	117.5 (3)	C15—C16—C17	112.17 (14)
C1—C2—H2	121.3	O4—C16—H16	107.7
C3—C2—H2	121.3	C15—C16—H16	107.7
C2—C3—C4	121.0 (2)	C17—C16—H16	107.7
C2—C3—H3	119.5	O5—C17—C16	109.05 (14)
C4—C3—H3	119.5	O5—C17—C18	108.25 (14)
C3—C4—C5	116.97 (19)	C16—C17—C18	112.69 (14)
C3—C4—C12	119.26 (17)	O5—C17—H17	108.9
C5—C4—C12	123.65 (17)	C16—C17—H17	108.9
N1—C5—N2	118.20 (19)	C18—C17—H17	108.9
N1—C5—C4	122.2 (2)	O6—C18—C17	106.93 (13)
N2—C5—C4	119.64 (19)	O6—C18—C19	109.34 (14)
C7—C6—N2	123.1 (2)	C17—C18—C19	110.54 (13)
C7—C6—C11	120.18 (19)	O6—C18—H18	110.0
N2—C6—C11	116.69 (19)	C17—C18—H18	110.0
C8—C7—C6	119.7 (2)	C19—C18—H18	110.0
C8—C7—H7	120.2	O7—C19—C20	107.05 (13)
C6—C7—H7	120.2	O7—C19—C18	111.99 (14)
C9—C8—C7	121.1 (2)	C20—C19—C18	113.24 (14)
C9—C8—H8	119.4	O7—C19—H19	108.1
C7—C8—H8	119.4	C20—C19—H19	108.1
C8—C9—C10	119.6 (2)	C18—C19—H19	108.1
C8—C9—H9	120.2	N3—C20—C19	109.40 (14)
C10—C9—H9	120.2	N3—C20—H20A	109.8
C9—C10—C11	121.1 (2)	C19—C20—H20A	109.8
C9—C10—C13	118.3 (2)	N3—C20—H20B	109.8
C11—C10—C13	120.5 (2)	C19—C20—H20B	109.8
C10—C11—C6	117.9 (2)	H20A—C20—H20B	108.2
C10—C11—C14	122.4 (2)	N3—C21—H21A	109.5
C6—C11—C14	119.69 (19)	N3—C21—H21B	109.5
O1—C12—O2	123.88 (17)	H21A—C21—H21B	109.5
O1—C12—C4	118.09 (18)	N3—C21—H21C	109.5
O2—C12—C4	118.02 (15)	H21A—C21—H21C	109.5
F2—C13—F1	105.9 (3)	H21B—C21—H21C	109.5
F2—C13—F3	105.8 (2)

C5—N1—C1—C2	1.1 (7)	N2—C6—C11—C14	−8.4 (3)
N1—C1—C2—C3	−2.2 (7)	C3—C4—C12—O1	18.5 (3)
C1—C2—C3—C4	0.5 (5)	C5—C4—C12—O1	−157.5 (2)
C2—C3—C4—C5	2.0 (4)	C3—C4—C12—O2	−162.5 (2)
C2—C3—C4—C12	−174.2 (3)	C5—C4—C12—O2	21.5 (3)
C1—N1—C5—N2	−178.8 (3)	C9—C10—C13—F2	−1.2 (4)
C1—N1—C5—C4	1.7 (5)	C11—C10—C13—F2	175.5 (2)
C6—N2—C5—N1	−26.6 (4)	C9—C10—C13—F1	−121.0 (3)
C6—N2—C5—C4	153.0 (2)	C11—C10—C13—F1	55.7 (4)
C3—C4—C5—N1	−3.2 (4)	C9—C10—C13—F3	118.7 (3)
C12—C4—C5—N1	172.9 (2)	C11—C10—C13—F3	−64.6 (3)
C3—C4—C5—N2	177.3 (2)	O3—C15—C16—O4	−68.73 (19)
C12—C4—C5—N2	−6.6 (3)	O3—C15—C16—C17	55.0 (2)
C5—N2—C6—C7	11.8 (3)	O4—C16—C17—O5	−179.99 (15)
C5—N2—C6—C11	−165.6 (2)	C15—C16—C17—O5	55.3 (2)
N2—C6—C7—C8	−172.3 (2)	O4—C16—C17—C18	−59.75 (19)
C11—C6—C7—C8	5.0 (3)	C15—C16—C17—C18	175.58 (15)
C6—C7—C8—C9	0.2 (4)	O5—C17—C18—O6	47.45 (17)
C7—C8—C9—C10	−3.2 (4)	C16—C17—C18—O6	−73.25 (17)
C8—C9—C10—C11	1.1 (3)	O5—C17—C18—C19	−71.48 (17)
C8—C9—C10—C13	177.8 (3)	C16—C17—C18—C19	167.82 (14)
C9—C10—C11—C6	3.9 (3)	O6—C18—C19—O7	49.79 (18)
C13—C10—C11—C6	−172.7 (2)	C17—C18—C19—O7	167.24 (14)
C9—C10—C11—C14	−177.2 (2)	O6—C18—C19—C20	170.96 (14)
C13—C10—C11—C14	6.2 (3)	C17—C18—C19—C20	−71.59 (19)
C7—C6—C11—C10	−6.9 (3)	C21—N3—C20—C19	136.7 (3)
N2—C6—C11—C10	170.58 (18)	O7—C19—C20—N3	−65.53 (18)
C7—C6—C11—C14	174.1 (2)	C18—C19—C20—N3	170.56 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.85 (2)	1.97 (2)	2.670 (2)	139 (2)
O4—H4O···O1	0.82	2.00	2.818 (2)	175
O6—H6O···O1ⁱ	0.82	1.95	2.757 (2)	170
O7—H7O···O2ⁱ	0.82	1.79	2.591 (2)	166
O3—H3O···O4ⁱⁱ	0.82	1.99	2.792 (2)	168
O5—H5O···O7ⁱⁱⁱ	0.82	1.79	2.608 (2)	178
N3—H3NA···O3^iv	0.86 (2)	2.01 (2)	2.776 (2)	148 (2)
N3—H3NB···O5ⁱⁱⁱ	0.87 (3)	2.05 (2)	2.767 (2)	139 (3)
N3—H3NB···O6ⁱⁱⁱ	0.87 (3)	2.16 (2)	2.894 (2)	142 (3)

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

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