DL-Valine DL-valinium picrate

The title compound, C₅H₁₂NO₂⁺·C₆H₂N₃O₇⁻·C₅H₁₁NO₂, crystallizes in the monoclinic system with one valinium cation, one valine mol­ecule and one picrate anion in the asymmetric unit. In the crystal structure, the valinium cation is linked to the picrate anion via O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.058
• wR factor = 0.181
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.
PLAT414_ALERT_2_B Short Intra D-H..H-X       H1A    ..  H5F     ..       1.86 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O13    ..  C1      ..       2.90 Ang.

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.648
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.65 e/A   3
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        N12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT432_ALERT_2_C Short Inter X...Y Contact  O13    ..  C2      ..       2.93 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O13    ..  C1'     ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         17

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

'DL-valine DL-valinium picrate '

Crystal data

C5H12NO2^+·C6H2N3O7^−·C5H11NO2	F(000) = 976
Mr = 463.41	Dx = 1.491 Mg m^−3 Dm = 1.489 Mg m^−3 Dm measured by Flotation technique using mixture of carbon tetracholride and xylene
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.3822 (4) Å	Cell parameters from 25 reflections
b = 23.221 (2) Å	θ = 9.8–14.1°
c = 16.579 (2) Å	µ = 0.13 mm^−1
β = 94.695 (7)°	T = 293 K
V = 2065.0 (3) Å^3	Block, yellow
Z = 4	0.3 × 0.2 × 0.15 mm

Data collection

MACH3 Nonius sealed tube diffractometer	2219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω–2θ scans	h = 0→6
Absorption correction: psi scan (North et al., 1968)	k = −1→27
Tmin = 0.970, Tmax = 0.981	l = −19→19
4297 measured reflections	3 standard reflections every 60 min
3642 independent reflections	intensity decay: none

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0782P)^2 + 2.0601P] where P = (Fo^2 + 2Fc^2)/3
3642 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.34 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. 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.8489 (5)	0.94681 (12)	0.92220 (15)	0.0402 (7)
O1B	0.5010 (4)	0.90248 (12)	0.87728 (16)	0.0403 (7)
C1	0.7240 (6)	0.91537 (15)	0.8728 (2)	0.0284 (8)
C2	0.8573 (6)	0.89051 (15)	0.8027 (2)	0.0291 (8)
H2	0.7352	0.8858	0.7560	0.035*
N1	1.0493 (6)	0.93352 (14)	0.78120 (19)	0.0379 (8)
H1A	1.1293	0.9201	0.7402	0.057*
H1B	1.1577	0.9394	0.8239	0.057*
H1C	0.9746	0.9666	0.7668	0.057*
C3	0.9840 (7)	0.83231 (16)	0.8209 (2)	0.0360 (9)
H3	1.1069	0.8375	0.8673	0.043*
C4	0.7984 (9)	0.78699 (19)	0.8434 (3)	0.0605 (13)
H4A	0.7138	0.8003	0.8887	0.091*	0.50
H4B	0.8851	0.7518	0.8576	0.091*	0.50
H4C	0.6790	0.7802	0.7981	0.091*	0.50
H4D	0.8048	0.7546	0.8076	0.091*	0.50
H4E	0.6335	0.8030	0.8387	0.091*	0.50
H4F	0.8396	0.7746	0.8981	0.091*	0.50
C5	1.1216 (8)	0.8119 (2)	0.7496 (3)	0.0521 (11)
H5A	1.2656	0.8357	0.7448	0.078*	0.50
H5B	1.0130	0.8145	0.7009	0.078*	0.50
H5C	1.1730	0.7726	0.7582	0.078*	0.50
H5D	1.0355	0.7796	0.7244	0.078*	0.50
H5E	1.2880	0.8007	0.7684	0.078*	0.50
H5F	1.1281	0.8426	0.7110	0.078*	0.50
O1A'	0.7186 (5)	0.95903 (13)	0.10851 (17)	0.0493 (8)
O1B'	0.6262 (5)	0.89988 (13)	0.20810 (17)	0.0469 (8)
H1'	0.763 (10)	0.913 (2)	0.227 (3)	0.070*
C1'	0.5811 (7)	0.92669 (16)	0.1389 (2)	0.0330 (9)
C2'	0.3226 (6)	0.91095 (16)	0.1001 (2)	0.0332 (8)
H2'	0.1993	0.9242	0.1363	0.040*
N1'	0.2827 (5)	0.94380 (14)	0.02351 (17)	0.0349 (7)
H1A'	0.1325	0.9357	−0.0003	0.052*
H1B'	0.3988	0.9341	−0.0093	0.052*
H1C'	0.2927	0.9813	0.0341	0.052*
C3'	0.2794 (9)	0.84625 (19)	0.0850 (3)	0.0545 (12)
H3'	0.1358	0.8439	0.0448	0.065*
C4'	0.4902 (12)	0.8173 (2)	0.0464 (3)	0.0812 (18)
H4A'	0.5229	0.8375	−0.0021	0.122*	0.50
H4B'	0.4452	0.7782	0.0333	0.122*	0.50
H4C'	0.6370	0.8177	0.0835	0.122*	0.50
H4D'	0.5472	0.7848	0.0786	0.122*	0.50
H4E'	0.6248	0.8441	0.0431	0.122*	0.50
H4F'	0.4330	0.8046	−0.0070	0.122*	0.50
C5'	0.2011 (12)	0.8161 (3)	0.1580 (4)	0.0835 (18)
H5A'	0.0680	0.8372	0.1796	0.125*	0.50
H5B'	0.3400	0.8138	0.1981	0.125*	0.50
H5C'	0.1449	0.7780	0.1435	0.125*	0.50
H5D'	0.3006	0.7822	0.1679	0.125*	0.50
H5E'	0.0286	0.8055	0.1494	0.125*	0.50
H5F'	0.2237	0.8413	0.2040	0.125*	0.50
C11	0.5836 (7)	0.04758 (16)	0.6224 (2)	0.0331 (8)
N11	0.4938 (6)	0.00098 (14)	0.66911 (19)	0.0398 (8)
O12	0.3206 (6)	−0.02879 (14)	0.63823 (18)	0.0581 (8)
O13	0.5832 (6)	−0.00796 (13)	0.73837 (17)	0.0546 (8)
C12	0.8106 (7)	0.07873 (16)	0.6496 (2)	0.0343 (9)
O11	0.9528 (5)	0.06328 (12)	0.71012 (16)	0.0479 (7)
C13	0.8561 (7)	0.12585 (17)	0.5970 (2)	0.0384 (9)
N12	1.0650 (7)	0.16568 (15)	0.6155 (3)	0.0505 (9)
O14	1.1427 (6)	0.19394 (16)	0.5611 (2)	0.0742 (10)
O15	1.1428 (9)	0.17084 (17)	0.6854 (3)	0.1037 (17)
C14	0.7164 (7)	0.13858 (18)	0.5265 (2)	0.0400 (10)
H14	0.7599	0.1692	0.4943	0.048*
C15	0.5094 (7)	0.10511 (18)	0.5039 (2)	0.0375 (9)
N13	0.3614 (7)	0.11846 (17)	0.4293 (2)	0.0487 (9)
O16	0.1805 (6)	0.08680 (15)	0.40975 (18)	0.0603 (9)
O17	0.4229 (7)	0.15872 (16)	0.38899 (19)	0.0707 (10)
C16	0.4430 (7)	0.06018 (17)	0.5515 (2)	0.0366 (9)
H16	0.3027	0.0382	0.5359	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0315 (14)	0.0493 (16)	0.0378 (15)	−0.0017 (12)	−0.0079 (12)	−0.0118 (13)
O1B	0.0191 (13)	0.0581 (18)	0.0440 (15)	−0.0066 (12)	0.0054 (11)	0.0015 (13)
C1	0.0243 (18)	0.0314 (19)	0.0284 (18)	0.0007 (15)	−0.0049 (15)	0.0058 (15)
C2	0.0192 (16)	0.039 (2)	0.0279 (18)	−0.0041 (15)	−0.0023 (14)	−0.0020 (16)
N1	0.0280 (16)	0.048 (2)	0.0383 (18)	−0.0027 (14)	0.0060 (13)	0.0056 (15)
C3	0.0263 (18)	0.041 (2)	0.040 (2)	0.0004 (17)	−0.0024 (16)	−0.0009 (18)
C4	0.054 (3)	0.045 (3)	0.084 (4)	−0.004 (2)	0.017 (3)	0.004 (2)
C5	0.040 (2)	0.057 (3)	0.059 (3)	0.013 (2)	0.006 (2)	−0.008 (2)
O1A'	0.0303 (14)	0.068 (2)	0.0478 (17)	−0.0141 (14)	−0.0067 (13)	0.0129 (15)
O1B'	0.0362 (16)	0.0612 (19)	0.0411 (16)	0.0003 (14)	−0.0102 (13)	0.0122 (14)
C1'	0.0275 (19)	0.037 (2)	0.033 (2)	0.0028 (17)	−0.0033 (16)	0.0001 (17)
C2'	0.0252 (18)	0.042 (2)	0.0322 (19)	−0.0011 (16)	−0.0020 (15)	−0.0015 (17)
N1'	0.0268 (15)	0.0411 (18)	0.0352 (17)	0.0001 (14)	−0.0074 (13)	−0.0017 (14)
C3'	0.059 (3)	0.045 (3)	0.058 (3)	−0.008 (2)	−0.003 (2)	−0.001 (2)
C4'	0.125 (5)	0.050 (3)	0.072 (4)	0.010 (3)	0.029 (4)	−0.011 (3)
C5'	0.082 (4)	0.072 (4)	0.097 (4)	−0.004 (3)	0.006 (3)	0.024 (3)
C11	0.0326 (19)	0.037 (2)	0.0292 (19)	0.0068 (17)	0.0003 (16)	0.0013 (16)
N11	0.0393 (19)	0.0431 (19)	0.0373 (19)	0.0073 (16)	0.0050 (15)	0.0016 (16)
O12	0.0572 (19)	0.067 (2)	0.0504 (18)	−0.0209 (17)	0.0080 (15)	0.0036 (16)
O13	0.0629 (19)	0.0580 (19)	0.0415 (17)	0.0083 (16)	−0.0039 (15)	0.0182 (15)
C12	0.0310 (19)	0.039 (2)	0.0323 (19)	0.0113 (17)	−0.0044 (16)	0.0002 (17)
O11	0.0437 (16)	0.0541 (18)	0.0422 (16)	0.0025 (14)	−0.0190 (13)	0.0077 (13)
C13	0.0297 (19)	0.043 (2)	0.041 (2)	0.0050 (18)	−0.0042 (17)	−0.0019 (18)
N12	0.042 (2)	0.041 (2)	0.065 (3)	0.0047 (17)	−0.0169 (19)	0.0060 (19)
O14	0.060 (2)	0.073 (2)	0.090 (3)	−0.0223 (19)	0.0076 (19)	0.014 (2)
O15	0.128 (4)	0.080 (3)	0.090 (3)	−0.047 (3)	−0.067 (3)	0.028 (2)
C14	0.039 (2)	0.047 (2)	0.033 (2)	0.0031 (19)	0.0012 (18)	0.0037 (18)
C15	0.036 (2)	0.051 (2)	0.0247 (18)	0.0089 (19)	−0.0053 (15)	0.0014 (18)
N13	0.048 (2)	0.066 (3)	0.0305 (18)	0.007 (2)	−0.0082 (16)	0.0057 (18)
O16	0.0472 (18)	0.084 (2)	0.0466 (17)	−0.0053 (17)	−0.0176 (15)	0.0033 (17)
O17	0.077 (2)	0.086 (3)	0.0456 (19)	−0.004 (2)	−0.0169 (17)	0.0303 (19)
C16	0.032 (2)	0.048 (2)	0.0289 (19)	0.0028 (18)	−0.0026 (16)	−0.0046 (17)

Geometric parameters (Å, º)

O1A—C1	1.251 (4)	C3'—C5'	1.489 (7)
O1B—C1	1.245 (4)	C3'—C4'	1.505 (7)
C1—C2	1.528 (5)	C3'—H3'	0.9800
C2—N1	1.501 (4)	C4'—H4A'	0.9600
C2—C3	1.533 (5)	C4'—H4B'	0.9600
C2—H2	0.9800	C4'—H4C'	0.9600
N1—H1A	0.8900	C4'—H4D'	0.9600
N1—H1B	0.8900	C4'—H4E'	0.9600
N1—H1C	0.8900	C4'—H4F'	0.9600
C3—C4	1.518 (6)	C5'—H5A'	0.9600
C3—C5	1.521 (6)	C5'—H5B'	0.9600
C3—H3	0.9800	C5'—H5C'	0.9600
C4—H4A	0.9600	C5'—H5D'	0.9600
C4—H4B	0.9600	C5'—H5E'	0.9600
C4—H4C	0.9600	C5'—H5F'	0.9600
C4—H4D	0.9600	C11—C16	1.375 (5)
C4—H4E	0.9600	C11—N11	1.438 (5)
C4—H4F	0.9600	C11—C12	1.460 (5)
C5—H5A	0.9600	N11—O13	1.226 (4)
C5—H5B	0.9600	N11—O12	1.237 (4)
C5—H5C	0.9600	C12—O11	1.263 (4)
C5—H5D	0.9600	C12—C13	1.433 (5)
C5—H5E	0.9600	C13—C14	1.370 (5)
C5—H5F	0.9600	C13—N12	1.468 (5)
O1A'—C1'	1.194 (5)	N12—O15	1.205 (5)
O1B'—C1'	1.311 (4)	N12—O14	1.217 (5)
O1B'—H1'	0.83 (5)	C14—C15	1.385 (6)
C1'—C2'	1.528 (5)	C14—H14	0.9300
C2'—N1'	1.482 (4)	C15—C16	1.373 (6)
C2'—C3'	1.538 (6)	C15—N13	1.449 (5)
C2'—H2'	0.9800	N13—O17	1.211 (5)
N1'—H1A'	0.8900	N13—O16	1.242 (5)
N1'—H1B'	0.8900	C16—H16	0.9300
N1'—H1C'	0.8900
O1B—C1—O1A	124.7 (3)	H1A'—N1'—H1C'	109.5
O1B—C1—C2	118.0 (3)	H1B'—N1'—H1C'	109.5
O1A—C1—C2	117.2 (3)	C5'—C3'—C4'	114.1 (4)
N1—C2—C1	107.7 (3)	C5'—C3'—C2'	112.1 (4)
N1—C2—C3	109.3 (3)	C4'—C3'—C2'	113.4 (4)
C1—C2—C3	114.3 (3)	C5'—C3'—H3'	105.4
N1—C2—H2	108.5	C4'—C3'—H3'	105.4
C1—C2—H2	108.5	C2'—C3'—H3'	105.4
C3—C2—H2	108.5	C3'—C4'—H4A'	109.5
C2—N1—H1A	109.5	C3'—C4'—H4B'	109.5
C2—N1—H1B	109.5	H4A'—C4'—H4B'	109.5
H1A—N1—H1B	109.5	C3'—C4'—H4C'	109.5
C2—N1—H1C	109.5	H4A'—C4'—H4C'	109.5
H1A—N1—H1C	109.5	H4B'—C4'—H4C'	109.5
H1B—N1—H1C	109.5	C3'—C4'—H4D'	109.5
C4—C3—C5	110.3 (4)	H4A'—C4'—H4D'	141.1
C4—C3—C2	111.6 (3)	H4B'—C4'—H4D'	56.3
C5—C3—C2	111.0 (3)	H4C'—C4'—H4D'	56.3
C4—C3—H3	107.9	C3'—C4'—H4E'	109.5
C5—C3—H3	107.9	H4A'—C4'—H4E'	56.3
C2—C3—H3	107.9	H4B'—C4'—H4E'	141.1
C3—C4—H4A	109.5	H4C'—C4'—H4E'	56.3
C3—C4—H4B	109.5	H4D'—C4'—H4E'	109.5
H4A—C4—H4B	109.5	C3'—C4'—H4F'	109.5
C3—C4—H4C	109.5	H4A'—C4'—H4F'	56.3
H4A—C4—H4C	109.5	H4B'—C4'—H4F'	56.3
H4B—C4—H4C	109.5	H4C'—C4'—H4F'	141.1
C3—C4—H4D	109.5	H4D'—C4'—H4F'	109.5
H4A—C4—H4D	141.1	H4E'—C4'—H4F'	109.5
H4B—C4—H4D	56.3	C3'—C5'—H5A'	109.5
H4C—C4—H4D	56.3	C3'—C5'—H5B'	109.5
C3—C4—H4E	109.5	H5A'—C5'—H5B'	109.5
H4A—C4—H4E	56.3	C3'—C5'—H5C'	109.5
H4B—C4—H4E	141.1	H5A'—C5'—H5C'	109.5
H4C—C4—H4E	56.3	H5B'—C5'—H5C'	109.5
H4D—C4—H4E	109.5	C3'—C5'—H5D'	109.5
C3—C4—H4F	109.5	H5A'—C5'—H5D'	141.1
H4A—C4—H4F	56.3	H5B'—C5'—H5D'	56.3
H4B—C4—H4F	56.3	H5C'—C5'—H5D'	56.3
H4C—C4—H4F	141.1	C3'—C5'—H5E'	109.5
H4D—C4—H4F	109.5	H5A'—C5'—H5E'	56.3
H4E—C4—H4F	109.5	H5B'—C5'—H5E'	141.1
C3—C5—H5A	109.5	H5C'—C5'—H5E'	56.3
C3—C5—H5B	109.5	H5D'—C5'—H5E'	109.5
H5A—C5—H5B	109.5	C3'—C5'—H5F'	109.5
C3—C5—H5C	109.5	H5A'—C5'—H5F'	56.3
H5A—C5—H5C	109.5	H5B'—C5'—H5F'	56.3
H5B—C5—H5C	109.5	H5C'—C5'—H5F'	141.1
C3—C5—H5D	109.5	H5D'—C5'—H5F'	109.5
H5A—C5—H5D	141.1	H5E'—C5'—H5F'	109.5
H5B—C5—H5D	56.3	C16—C11—N11	115.8 (3)
H5C—C5—H5D	56.3	C16—C11—C12	123.2 (3)
C3—C5—H5E	109.5	N11—C11—C12	121.1 (3)
H5A—C5—H5E	56.3	O13—N11—O12	121.2 (3)
H5B—C5—H5E	141.1	O13—N11—C11	120.6 (3)
H5C—C5—H5E	56.3	O12—N11—C11	118.2 (3)
H5D—C5—H5E	109.5	O11—C12—C13	125.3 (4)
C3—C5—H5F	109.5	O11—C12—C11	122.9 (3)
H5A—C5—H5F	56.3	C13—C12—C11	111.7 (3)
H5B—C5—H5F	56.3	C14—C13—C12	125.1 (4)
H5C—C5—H5F	141.1	C14—C13—N12	113.6 (4)
H5D—C5—H5F	109.5	C12—C13—N12	121.3 (3)
H5E—C5—H5F	109.5	O15—N12—O14	123.0 (4)
C1'—O1B'—H1'	105 (4)	O15—N12—C13	117.6 (4)
O1A'—C1'—O1B'	126.2 (3)	O14—N12—C13	119.2 (4)
O1A'—C1'—C2'	123.2 (3)	C13—C14—C15	118.9 (4)
O1B'—C1'—C2'	110.6 (3)	C13—C14—H14	120.6
N1'—C2'—C1'	107.5 (3)	C15—C14—H14	120.6
N1'—C2'—C3'	110.7 (3)	C16—C15—C14	120.9 (3)
C1'—C2'—C3'	115.0 (3)	C16—C15—N13	120.2 (4)
N1'—C2'—H2'	107.8	C14—C15—N13	119.0 (4)
C1'—C2'—H2'	107.8	O17—N13—O16	123.9 (3)
C3'—C2'—H2'	107.8	O17—N13—C15	118.7 (4)
C2'—N1'—H1A'	109.5	O16—N13—C15	117.4 (4)
C2'—N1'—H1B'	109.5	C15—C16—C11	120.1 (4)
H1A'—N1'—H1B'	109.5	C15—C16—H16	119.9
C2'—N1'—H1C'	109.5	C11—C16—H16	119.9
O1A—C1—C2—N1	−32.3 (4)	C16—C11—C12—C13	4.2 (5)
O1B—C1—C2—N1	148.5 (3)	N11—C11—C12—C13	−176.0 (3)
O1A—C1—C2—C3	89.3 (4)	O11—C12—C13—C14	172.3 (4)
O1B—C1—C2—C3	−89.9 (4)	C11—C12—C13—C14	−4.2 (5)
N1—C2—C3—C4	179.8 (3)	O11—C12—C13—N12	−7.7 (6)
C1—C2—C3—C4	59.0 (4)	C11—C12—C13—N12	175.8 (3)
N1—C2—C3—C5	−56.7 (4)	C14—C13—N12—O15	155.2 (4)
C1—C2—C3—C5	−177.5 (3)	C12—C13—N12—O15	−24.9 (6)
O1A'—C1'—C2'—N1'	−1.5 (5)	C14—C13—N12—O14	−21.1 (5)
O1B'—C1'—C2'—N1'	178.6 (3)	C12—C13—N12—O14	158.9 (4)
O1A'—C1'—C2'—C3'	122.3 (4)	C12—C13—C14—C15	2.1 (6)
O1B'—C1'—C2'—C3'	−57.6 (4)	N12—C13—C14—C15	−178.0 (3)
N1'—C2'—C3'—C5'	−153.4 (4)	C13—C14—C15—C16	0.6 (6)
C1'—C2'—C3'—C5'	84.6 (5)	C13—C14—C15—N13	−180.0 (4)
N1'—C2'—C3'—C4'	75.6 (5)	C16—C15—N13—O17	179.2 (4)
C1'—C2'—C3'—C4'	−46.4 (5)	C14—C15—N13—O17	−0.3 (6)
C16—C11—N11—O13	−169.0 (3)	C16—C15—N13—O16	−2.2 (6)
C12—C11—N11—O13	11.2 (5)	C14—C15—N13—O16	178.3 (4)
C16—C11—N11—O12	9.3 (5)	C14—C15—C16—C11	−0.5 (6)
C12—C11—N11—O12	−170.5 (3)	N13—C15—C16—C11	−180.0 (4)
C16—C11—C12—O11	−172.4 (4)	N11—C11—C16—C15	178.0 (3)
N11—C11—C12—O11	7.4 (6)	C12—C11—C16—C15	−2.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O12^i	0.89	2.37	3.014 (4)	129
N1—H1B···O1B^ii	0.89	2.16	2.887 (4)	138
N1—H1C···O13^iii	0.89	2.20	2.890 (4)	134
N1—H1C···O11^iii	0.89	2.43	3.261 (4)	155
O1B′—H1′···O11^iv	0.83 (5)	1.86 (5)	2.684 (4)	168 (5)
N1′—H1C′···O1A^v	0.89	2.00	2.805 (4)	151
N1′—H1B′···O1B^vi	0.89	2.13	2.940 (4)	150
N1′—H1A′···O1A^vii	0.89	1.93	2.763 (4)	155

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