cis-3-(tert-Butoxy­carbonyl­amino)cyclo­hexa­necarboxylic acid

Hu, Y.; Sun, X.X.; Guo, Y.; Yao, H.

doi:10.1107/S1600536808027098

cis-3-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid

The title compound, C₁₂H₂₁NO₄, a γ-aminobutyric acid derivative, crystallizes with two molecules in the asymmetric unit. The crystal structure is stabilized by intermolecular N—H

O and O—H

O hydrogen bonds, forming a strand. An intramolecular N—H

O hydrogen bond is also observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808027098/bt2775sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808027098/bt2775Isup2.hkl Contains datablock I

CCDC reference: 702578

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.110
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.767     0.921
            Tmin(prime) and Tmax expected:      0.950     0.982
            RR(prime) =      0.861
            Please check that your absorption correction is appropriate.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT061_ALERT_4_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.07
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       2000 Deg.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.066
            Tmax scaled      0.982 Tmin scaled      0.818
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_4_G Check the Absolute Configuration of C2     .....          R
PLAT793_ALERT_4_G Check the Absolute Configuration of C6     .....          S
PLAT793_ALERT_4_G Check the Absolute Configuration of C14    .....          S
PLAT793_ALERT_4_G Check the Absolute Configuration of C18    .....          R

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

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

Comment top

γ aminobutyric acid (GABA) and its derivatives have an extensive appliction in medicine. For instance, GABA is an important inhibitory neurotransmitter in certain neurological and psychiatric disorders (Schousboe, 2000; Roberts et al., 1976). As the analogue of GABA, cis-3-aminocyclohexanecarboxylic acid is an inhibitor of GABA uptake (Allan et al., 1981). cis-3-aminocyclohexanecarboxylic acid is incorporated in cyclic peptides and organic nanotubes (Amorin et al., 2003). The title compound is a key intermediate for the synthesis of cis-3- aminocyclohexanecarboxylic acid (Hu et al., 2006). The synthesis and crystal structure of the title compound are described in this paper.

Interolecular O-H···O hydrogen bonds result in eight-membered rings that can be described in terms of graph-set notation as R₂²(8) (Figure 2).

One-dimensional strands are formed along the crystallographic b axis by N-H···O hydrogen bonds (Figure 2 and Table 2).

Related literature top

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

Experimental top

cis-3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid was synthesized from 3-aminobenzoic acid (Amorin et al., 2003). The compound identity was conformed by the NMR spectra and IR. Crystal were obtained from ethyl acetate by solvent evaporation. ¹H NMR in CDCl₃ (300 MHz): 9.20–10.4 (br, 1H,), 5.72 (s, 1H), 4.82 (s, H), 3.67–3.74 (m, 1H), 1.43 (s, 9H), 1.05–2.40 (m, 8H).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); 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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the two molecules in the asymmetric unit of the title compound, with anisotropic displacement parameters drawn at the 50% probability level.
	Fig. 2. A view of the hydrogen-bonded strands (Dashed lines). The strands are aligned parallel to the crystallographic b axis. H atoms not involved in H-bonding have been omitted for clarity. Symmetry codes: () x,y+1,z; () x,y-1,z; (#) 1 - x,1 - y,-z; (##) 1 - x,2 - y*,-z.

cis-3-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid top

Crystal data top

C₁₂H₂₁NO₄	Z = 4
M_r = 243.30	F(000) = 528
Triclinic, P1	D_x = 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 = 4.1–13.9°
α = 85.64 (2)°	µ = 0.09 mm⁻¹
β = 88.68 (2)°	T = 296 K
γ = 88.51 (2)°	Block, colorless
V = 1342.6 (4) Å³	0.56 × 0.46 × 0.20 mm

Data collection top

Bruker SMART 1K area-detector diffractometer	4822 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 25.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→7
T_min = 0.767, T_max = 0.921	k = −11→11
5514 measured reflections	l = −27→27

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0564P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
4822 reflections	Δρ_max = 0.22 e Å⁻³
324 parameters	Δρ_min = −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)

Crystal data top

C₁₂H₂₁NO₄	γ = 88.51 (2)°
M_r = 243.30	V = 1342.6 (4) Å³
Triclinic, P1	Z = 4
a = 5.854 (1) Å	Mo Kα radiation
b = 10.000 (2) Å	µ = 0.09 mm⁻¹
c = 23.014 (5) Å	T = 296 K
α = 85.64 (2)°	0.56 × 0.46 × 0.20 mm
β = 88.68 (2)°

Data collection top

Bruker SMART 1K area-detector diffractometer	4822 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2483 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.921	R_int = 0.017
5514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.22 e Å⁻³
4822 reflections	Δρ_min = −0.17 e Å⁻³
324 parameters

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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6	0.86 (1)	2.16 (1)	3.009 (2)	169 (2)
N2—H2A···O2ⁱ	0.85 (1)	2.18 (1)	3.013 (2)	165 (2)
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) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₁NO₄
M_r	243.30
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.854 (1), 10.000 (2), 23.014 (5)
α, β, γ (°)	85.64 (2), 88.68 (2), 88.51 (2)
V (Å³)	1342.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.56 × 0.46 × 0.20

Data collection
Diffractometer	Bruker SMART 1K area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.767, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	5514, 4822, 2483
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.109, 0.81
No. of reflections	4822
No. of parameters	324
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).