cis-3-(tert-Butoxy-carbonyl-amino)cyclo-hexa-necarboxylic acid.

The title compound, C(12)H(21)NO(4), a γ-aminobutyric acid derivative, crystallizes with two mol-ecules in the asymmetric unit. The crystal structure is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming a strand. An intramolecular N-H⋯O hydrogen bond is also observed.

Related literature

For related literature, see: Allan et al. (1981 ▶); Amorin et al. (2003 ▶); Hu et al. (2006 ▶); Roberts et al. (1976 ▶); Schousboe (2000 ▶).

Experimental

Crystal data

C12H21NO4

M = 243.30

Triclinic,

a = 5.854 (1) Å

b = 10.000 (2) Å

c = 23.014 (5) Å

α = 85.64 (2)°

β = 88.68 (2)°

γ = 88.51 (2)°

V = 1342.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.56 × 0.46 × 0.20 mm

Data collection

Bruker SMART 1K area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.767, T max = 0.921 (expected range = 0.818–0.982)

5514 measured reflections

4822 independent reflections

2483 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 0.81

4822 reflections

324 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027098/bt2775sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027098/bt2775Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H21NO4	Z = 4
Mr = 243.30	F000 = 528
Triclinic, P1	Dx = 1.204 Mg m−3
Hall symbol: -P 1	Melting point: 409 K
a = 5.854 (1) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.000 (2) Å	Cell parameters from 29 reflections
c = 23.014 (5) Å	θ = 4.1–13.9º
α = 85.64 (2)º	µ = 0.09 mm−1
β = 88.68 (2)º	T = 296 (2) K
γ = 88.51 (2)º	Block, colorless
V = 1342.6 (4) Å3	0.56 × 0.46 × 0.20 mm

Bruker SMART 1K area-detector diffractometer	4822 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 293(2) K	θmax = 25.3º
phi and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = 0→7
Tmin = 0.767, Tmax = 0.921	k = −11→11
5514 measured reflections	l = −27→27

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max < 0.001
4822 reflections	Δρmax = 0.22 e Å−3
324 parameters	Δρmin = −0.17 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0098 (13)

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.

	x	y	z	Uiso*/Ueq
O1	0.6276 (3)	0.87356 (14)	0.15126 (6)	0.0548 (5)
O2	0.5946 (3)	1.03347 (15)	0.21599 (7)	0.0620 (5)
O3	0.6134 (3)	0.64184 (19)	0.45997 (9)	0.0823 (6)
H3	0.6355	0.5778	0.4838	0.099*
O4	0.2737 (3)	0.55582 (18)	0.46040 (8)	0.0797 (6)
N1	0.4694 (4)	0.82327 (18)	0.23756 (7)	0.0481 (5)
C1	0.4318 (4)	0.7291 (2)	0.33857 (8)	0.0408 (5)
H1C	0.5960	0.7136	0.3392	0.049*
H1B	0.3623	0.6490	0.3265	0.049*
C2	0.3427 (4)	0.7572 (2)	0.39994 (8)	0.0384 (5)
H2	0.4183	0.8372	0.4113	0.046*
C3	0.0867 (4)	0.7873 (2)	0.39991 (9)	0.0467 (6)
H3A	0.0069	0.7080	0.3906	0.056*
H3B	0.0358	0.8099	0.4384	0.056*
C4	0.0288 (4)	0.9027 (2)	0.35566 (10)	0.0525 (6)
H4A	0.0938	0.9843	0.3677	0.063*
H4B	−0.1358	0.9160	0.3546	0.063*
C5	0.1199 (4)	0.8768 (2)	0.29489 (9)	0.0536 (6)
H5A	0.0424	0.8011	0.2810	0.064*
H5B	0.0880	0.9547	0.2684	0.064*
C6	0.3752 (4)	0.8474 (2)	0.29527 (8)	0.0403 (5)
H6	0.4493	0.9263	0.3083	0.048*
C7	0.5654 (4)	0.9200 (2)	0.20301 (9)	0.0437 (6)
C8	0.7620 (4)	0.9548 (2)	0.10769 (9)	0.0483 (6)
C9	0.6330 (5)	1.0795 (3)	0.08659 (11)	0.0732 (8)
H9A	0.4824	1.0567	0.0756	0.088*
H9B	0.7120	1.1221	0.0535	0.088*
H9C	0.6216	1.1397	0.1171	0.088*
C10	0.7906 (6)	0.8626 (3)	0.05895 (11)	0.0877 (10)
H10A	0.8705	0.7819	0.0729	0.105*
H10B	0.8766	0.9066	0.0273	0.105*
H10C	0.6430	0.8408	0.0456	0.105*
C11	0.9874 (5)	0.9845 (3)	0.13189 (13)	0.0946 (11)
H11A	0.9663	1.0492	0.1604	0.114*
H11B	1.0866	1.0200	0.1010	0.114*
H11C	1.0546	0.9036	0.1499	0.114*
C12	0.4076 (4)	0.6421 (2)	0.44293 (9)	0.0414 (5)
O5	0.3565 (3)	0.37430 (14)	0.15151 (6)	0.0550 (5)
O6	0.3842 (3)	0.53682 (15)	0.21453 (6)	0.0597 (5)
O7	0.3647 (3)	0.1116 (2)	0.44631 (8)	0.0765 (6)
H7	0.3445	0.0571	0.4743	0.092*
O8	0.7245 (3)	0.08103 (17)	0.47100 (7)	0.0692 (5)
N2	0.5105 (3)	0.32454 (17)	0.23698 (7)	0.0458 (5)
C13	0.5512 (4)	0.2287 (2)	0.33700 (8)	0.0401 (5)
H13A	0.6327	0.1504	0.3240	0.048*
H13B	0.3892	0.2102	0.3385	0.048*
C14	0.6306 (4)	0.2564 (2)	0.39808 (8)	0.0382 (5)
H14	0.5424	0.3347	0.4100	0.046*
C15	0.8821 (4)	0.2927 (2)	0.39721 (9)	0.0477 (6)
H15A	0.9757	0.2159	0.3873	0.057*
H15B	0.9243	0.3159	0.4356	0.057*
C16	0.9262 (4)	0.4108 (2)	0.35278 (10)	0.0543 (6)
H16A	0.8474	0.4902	0.3656	0.065*
H16B	1.0886	0.4280	0.3507	0.065*
C17	0.8453 (4)	0.3842 (2)	0.29241 (9)	0.0536 (6)
H17A	0.8678	0.4634	0.2660	0.064*
H17B	0.9358	0.3110	0.2777	0.064*
C18	0.5954 (4)	0.3489 (2)	0.29415 (8)	0.0395 (5)
H18	0.5081	0.4256	0.3080	0.047*
C19	0.4147 (4)	0.4221 (2)	0.20222 (9)	0.0426 (6)
C20	0.2250 (4)	0.4572 (2)	0.10807 (9)	0.0482 (6)
C21	0.3591 (5)	0.5763 (3)	0.08456 (11)	0.0705 (8)
H21A	0.3771	0.6359	0.1148	0.085*
H21B	0.2791	0.6225	0.0528	0.085*
H21C	0.5069	0.5465	0.0710	0.085*
C22	0.1969 (6)	0.3620 (3)	0.06073 (11)	0.0893 (10)
H22A	0.3447	0.3347	0.0463	0.107*
H22B	0.1117	0.4065	0.0294	0.107*
H22C	0.1164	0.2845	0.0764	0.107*
C23	−0.0011 (5)	0.4961 (3)	0.13346 (12)	0.0863 (10)
H23A	−0.0716	0.4182	0.1522	0.104*
H23B	−0.0972	0.5346	0.1030	0.104*
H23C	0.0198	0.5607	0.1616	0.104*
C24	0.5776 (4)	0.1408 (2)	0.44197 (9)	0.0426 (6)
H1A	0.452 (4)	0.7445 (12)	0.2264 (9)	0.048 (7)*
H2A	0.522 (3)	0.2460 (12)	0.2249 (8)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0864 (13)	0.0413 (9)	0.0361 (9)	−0.0087 (8)	0.0145 (8)	−0.0006 (7)
O2	0.1046 (15)	0.0365 (9)	0.0447 (10)	−0.0099 (9)	0.0104 (9)	−0.0030 (8)
O3	0.0604 (13)	0.0895 (15)	0.0894 (15)	−0.0081 (11)	−0.0195 (11)	0.0498 (11)
O4	0.0745 (14)	0.0736 (13)	0.0854 (14)	−0.0219 (11)	−0.0229 (10)	0.0437 (11)
N1	0.0844 (16)	0.0307 (11)	0.0288 (10)	−0.0057 (10)	0.0068 (9)	−0.0015 (9)
C1	0.0493 (14)	0.0388 (12)	0.0334 (12)	0.0036 (10)	0.0013 (10)	0.0006 (9)
C2	0.0499 (14)	0.0344 (11)	0.0305 (11)	−0.0003 (10)	−0.0030 (10)	0.0003 (9)
C3	0.0507 (15)	0.0479 (14)	0.0408 (13)	0.0026 (11)	0.0020 (11)	−0.0007 (11)
C4	0.0536 (16)	0.0525 (14)	0.0504 (14)	0.0098 (12)	−0.0034 (12)	0.0003 (12)
C5	0.0667 (18)	0.0530 (15)	0.0399 (14)	0.0098 (13)	−0.0113 (12)	0.0041 (11)
C6	0.0584 (16)	0.0356 (12)	0.0266 (11)	0.0001 (11)	−0.0007 (10)	−0.0006 (9)
C7	0.0648 (17)	0.0345 (13)	0.0313 (12)	0.0029 (11)	−0.0034 (11)	0.0006 (10)
C8	0.0589 (16)	0.0491 (14)	0.0350 (12)	−0.0040 (12)	0.0051 (11)	0.0082 (11)
C9	0.087 (2)	0.0726 (18)	0.0554 (16)	0.0072 (16)	0.0048 (15)	0.0203 (14)
C10	0.139 (3)	0.073 (2)	0.0496 (17)	−0.0045 (19)	0.0331 (17)	−0.0041 (15)
C11	0.066 (2)	0.142 (3)	0.071 (2)	−0.012 (2)	−0.0066 (16)	0.028 (2)
C12	0.0492 (16)	0.0454 (14)	0.0294 (12)	−0.0024 (12)	−0.0003 (11)	−0.0003 (10)
O5	0.0900 (13)	0.0407 (9)	0.0344 (9)	0.0082 (8)	−0.0216 (8)	−0.0015 (7)
O6	0.1010 (14)	0.0325 (9)	0.0460 (10)	0.0044 (9)	−0.0174 (9)	−0.0025 (7)
O7	0.0646 (13)	0.0912 (15)	0.0673 (13)	−0.0167 (11)	−0.0103 (10)	0.0429 (10)
O8	0.0616 (12)	0.0802 (12)	0.0598 (11)	0.0021 (10)	−0.0067 (9)	0.0342 (10)
N2	0.0777 (15)	0.0305 (11)	0.0291 (10)	0.0044 (10)	−0.0097 (9)	−0.0011 (9)
C13	0.0491 (14)	0.0377 (12)	0.0334 (12)	−0.0032 (10)	−0.0063 (10)	0.0011 (9)
C14	0.0526 (15)	0.0335 (11)	0.0281 (11)	−0.0002 (10)	−0.0027 (10)	0.0006 (9)
C15	0.0576 (16)	0.0470 (14)	0.0385 (13)	−0.0052 (11)	−0.0095 (11)	0.0003 (10)
C16	0.0569 (16)	0.0544 (15)	0.0516 (15)	−0.0155 (12)	−0.0063 (12)	0.0035 (12)
C17	0.0651 (18)	0.0549 (15)	0.0389 (13)	−0.0094 (13)	0.0045 (12)	0.0093 (11)
C18	0.0570 (15)	0.0332 (11)	0.0281 (11)	0.0003 (10)	−0.0029 (10)	−0.0002 (9)
C19	0.0587 (16)	0.0353 (13)	0.0333 (12)	−0.0016 (11)	−0.0043 (11)	0.0008 (10)
C20	0.0588 (16)	0.0518 (14)	0.0322 (12)	0.0036 (12)	−0.0077 (11)	0.0098 (11)
C21	0.078 (2)	0.0773 (19)	0.0532 (16)	−0.0065 (16)	−0.0084 (14)	0.0206 (14)
C22	0.138 (3)	0.076 (2)	0.0557 (18)	0.0055 (19)	−0.0464 (18)	−0.0007 (15)
C23	0.063 (2)	0.125 (3)	0.0653 (19)	0.0061 (18)	−0.0004 (15)	0.0247 (18)
C24	0.0528 (16)	0.0483 (14)	0.0265 (11)	−0.0041 (12)	−0.0032 (11)	−0.0007 (10)

O1—C7	1.350 (2)	O5—C19	1.349 (2)
O1—C8	1.468 (2)	O5—C20	1.468 (2)
O2—C7	1.212 (2)	O6—C19	1.210 (2)
O3—C12	1.276 (3)	O7—C24	1.288 (3)
O3—H3	0.8200	O7—H7	0.8200
O4—C12	1.220 (2)	O8—C24	1.217 (2)
N1—C7	1.332 (3)	N2—C19	1.334 (3)
N1—C6	1.461 (3)	N2—C18	1.457 (3)
N1—H1A	0.856 (9)	N2—H2A	0.854 (9)
C1—C6	1.522 (3)	C13—C18	1.519 (3)
C1—C2	1.538 (3)	C13—C14	1.538 (3)
C1—H1C	0.9700	C13—H13A	0.9700
C1—H1B	0.9700	C13—H13B	0.9700
C2—C12	1.507 (3)	C14—C24	1.510 (3)
C2—C3	1.521 (3)	C14—C15	1.525 (3)
C2—H2	0.9800	C14—H14	0.9800
C3—C4	1.517 (3)	C15—C16	1.526 (3)
C3—H3A	0.9700	C15—H15A	0.9700
C3—H3B	0.9700	C15—H15B	0.9700
C4—C5	1.524 (3)	C16—C17	1.522 (3)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—C6	1.515 (3)	C17—C18	1.513 (3)
C5—H5A	0.9700	C17—H17A	0.9700
C5—H5B	0.9700	C17—H17B	0.9700
C6—H6	0.9800	C18—H18	0.9800
C8—C11	1.490 (3)	C20—C23	1.489 (3)
C8—C9	1.496 (3)	C20—C21	1.503 (3)
C8—C10	1.509 (3)	C20—C22	1.515 (3)
C9—H9A	0.9600	C21—H21A	0.9600
C9—H9B	0.9600	C21—H21B	0.9600
C9—H9C	0.9600	C21—H21C	0.9600
C10—H10A	0.9600	C22—H22A	0.9600
C10—H10B	0.9600	C22—H22B	0.9600
C10—H10C	0.9600	C22—H22C	0.9600
C11—H11A	0.9600	C23—H23A	0.9600
C11—H11B	0.9600	C23—H23B	0.9600
C11—H11C	0.9600	C23—H23C	0.9600
C7—O1—C8	121.42 (16)	C19—O5—C20	121.23 (16)
C12—O3—H3	109.5	C24—O7—H7	109.5
C7—N1—C6	122.03 (18)	C19—N2—C18	121.92 (17)
C7—N1—H1A	122.0 (15)	C19—N2—H2A	118.2 (14)
C6—N1—H1A	115.9 (15)	C18—N2—H2A	119.8 (14)
C6—C1—C2	110.34 (16)	C18—C13—C14	110.31 (16)
C6—C1—H1C	109.6	C18—C13—H13A	109.6
C2—C1—H1C	109.6	C14—C13—H13A	109.6
C6—C1—H1B	109.6	C18—C13—H13B	109.6
C2—C1—H1B	109.6	C14—C13—H13B	109.6
H1C—C1—H1B	108.1	H13A—C13—H13B	108.1
C12—C2—C3	112.57 (18)	C24—C14—C15	112.45 (18)
C12—C2—C1	109.99 (16)	C24—C14—C13	111.16 (16)
C3—C2—C1	110.88 (17)	C15—C14—C13	111.45 (17)
C12—C2—H2	107.7	C24—C14—H14	107.2
C3—C2—H2	107.7	C15—C14—H14	107.2
C1—C2—H2	107.7	C13—C14—H14	107.2
C4—C3—C2	110.80 (18)	C14—C15—C16	110.42 (18)
C4—C3—H3A	109.5	C14—C15—H15A	109.6
C2—C3—H3A	109.5	C16—C15—H15A	109.6
C4—C3—H3B	109.5	C14—C15—H15B	109.6
C2—C3—H3B	109.5	C16—C15—H15B	109.6
H3A—C3—H3B	108.1	H15A—C15—H15B	108.1
C3—C4—C5	111.78 (18)	C17—C16—C15	111.92 (18)
C3—C4—H4A	109.3	C17—C16—H16A	109.2
C5—C4—H4A	109.3	C15—C16—H16A	109.2
C3—C4—H4B	109.3	C17—C16—H16B	109.2
C5—C4—H4B	109.3	C15—C16—H16B	109.2
H4A—C4—H4B	107.9	H16A—C16—H16B	107.9
C6—C5—C4	111.06 (18)	C18—C17—C16	111.07 (18)
C6—C5—H5A	109.4	C18—C17—H17A	109.4
C4—C5—H5A	109.4	C16—C17—H17A	109.4
C6—C5—H5B	109.4	C18—C17—H17B	109.4
C4—C5—H5B	109.4	C16—C17—H17B	109.4
H5A—C5—H5B	108.0	H17A—C17—H17B	108.0
N1—C6—C5	112.69 (18)	N2—C18—C17	112.74 (18)
N1—C6—C1	110.26 (16)	N2—C18—C13	110.10 (16)
C5—C6—C1	110.66 (18)	C17—C18—C13	111.08 (17)
N1—C6—H6	107.7	N2—C18—H18	107.6
C5—C6—H6	107.7	C17—C18—H18	107.6
C1—C6—H6	107.7	C13—C18—H18	107.6
O2—C7—N1	125.2 (2)	O6—C19—N2	124.8 (2)
O2—C7—O1	124.5 (2)	O6—C19—O5	125.00 (19)
N1—C7—O1	110.26 (18)	N2—C19—O5	110.16 (18)
O1—C8—C11	109.95 (19)	O5—C20—C23	110.03 (18)
O1—C8—C9	111.3 (2)	O5—C20—C21	110.79 (19)
C11—C8—C9	112.2 (2)	C23—C20—C21	112.6 (2)
O1—C8—C10	102.23 (18)	O5—C20—C22	102.20 (18)
C11—C8—C10	111.0 (2)	C23—C20—C22	110.8 (2)
C9—C8—C10	109.7 (2)	C21—C20—C22	109.9 (2)
C8—C9—H9A	109.5	C20—C21—H21A	109.5
C8—C9—H9B	109.5	C20—C21—H21B	109.5
H9A—C9—H9B	109.5	H21A—C21—H21B	109.5
C8—C9—H9C	109.5	C20—C21—H21C	109.5
H9A—C9—H9C	109.5	H21A—C21—H21C	109.5
H9B—C9—H9C	109.5	H21B—C21—H21C	109.5
C8—C10—H10A	109.5	C20—C22—H22A	109.5
C8—C10—H10B	109.5	C20—C22—H22B	109.5
H10A—C10—H10B	109.5	H22A—C22—H22B	109.5
C8—C10—H10C	109.5	C20—C22—H22C	109.5
H10A—C10—H10C	109.5	H22A—C22—H22C	109.5
H10B—C10—H10C	109.5	H22B—C22—H22C	109.5
C8—C11—H11A	109.5	C20—C23—H23A	109.5
C8—C11—H11B	109.5	C20—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C8—C11—H11C	109.5	C20—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
O4—C12—O3	122.4 (2)	O8—C24—O7	123.0 (2)
O4—C12—C2	122.7 (2)	O8—C24—C14	122.6 (2)
O3—C12—C2	114.9 (2)	O7—C24—C14	114.4 (2)
C6—C1—C2—C12	−177.75 (18)	C18—C13—C14—C24	177.21 (18)
C6—C1—C2—C3	57.1 (2)	C18—C13—C14—C15	−56.5 (2)
C12—C2—C3—C4	−179.43 (18)	C24—C14—C15—C16	−179.33 (18)
C1—C2—C3—C4	−55.7 (2)	C13—C14—C15—C16	55.1 (2)
C2—C3—C4—C5	55.1 (3)	C14—C15—C16—C17	−54.7 (3)
C3—C4—C5—C6	−55.6 (3)	C15—C16—C17—C18	55.7 (3)
C7—N1—C6—C5	95.8 (3)	C19—N2—C18—C17	−91.8 (3)
C7—N1—C6—C1	−140.0 (2)	C19—N2—C18—C13	143.5 (2)
C4—C5—C6—N1	−179.42 (18)	C16—C17—C18—N2	179.19 (17)
C4—C5—C6—C1	56.6 (2)	C16—C17—C18—C13	−56.7 (2)
C2—C1—C6—N1	177.30 (18)	C14—C13—C18—N2	−177.45 (17)
C2—C1—C6—C5	−57.4 (2)	C14—C13—C18—C17	56.9 (2)
C6—N1—C7—O2	3.7 (4)	C18—N2—C19—O6	−1.7 (4)
C6—N1—C7—O1	−176.82 (19)	C18—N2—C19—O5	178.42 (19)
C8—O1—C7—O2	6.9 (3)	C20—O5—C19—O6	−6.7 (3)
C8—O1—C7—N1	−172.59 (19)	C20—O5—C19—N2	173.15 (19)
C7—O1—C8—C11	61.5 (3)	C19—O5—C20—C23	−60.9 (3)
C7—O1—C8—C9	−63.5 (3)	C19—O5—C20—C21	64.3 (3)
C7—O1—C8—C10	179.4 (2)	C19—O5—C20—C22	−178.6 (2)
C3—C2—C12—O4	23.3 (3)	C15—C14—C24—O8	−3.1 (3)
C1—C2—C12—O4	−100.9 (3)	C13—C14—C24—O8	122.6 (2)
C3—C2—C12—O3	−156.4 (2)	C15—C14—C24—O7	176.5 (2)
C1—C2—C12—O3	79.5 (3)	C13—C14—C24—O7	−57.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6	0.856 (9)	2.163 (10)	3.009 (2)	169 (2)
N2—H2A···O2i	0.854 (9)	2.180 (11)	3.013 (2)	164.9 (19)
O3—H3···O4ii	0.82	1.86	2.672 (2)	172
O7—H7···O8iii	0.82	1.84	2.656 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6	0.856 (9)	2.163 (10)	3.009 (2)	169 (2)
N2—H2A⋯O2i	0.854 (9)	2.180 (11)	3.013 (2)	164.9 (19)
O3—H3⋯O4ii	0.82	1.86	2.672 (2)	172
O7—H7⋯O8iii	0.82	1.84	2.656 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) .