Bis{[1-(tert-butoxy­carbonyl)­pyrrolidin-2-yl]meth­yl} carbonate

Jing, L.-H.

doi:10.1107/S1600536809039452

organic compounds

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Volume 65| Part 11| November 2009| Page o2610

https://doi.org/10.1107/S1600536809039452

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Bis{[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methyl} carbonate

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 27 September 2009; accepted 28 September 2009; online 3 October 2009)

The asymmetric unit of the title compound, C₂₁H₃₆N₂O₇, consists of two independent half-molecules, the other halves being generated by twofold rotational axes. The two independent half-molecules are related by a pseudo-inversion center. In one, the pyrrolidine ring adopts a twist conformation whereas in the other it is in an envelope conformation. The crystal packing is stabilized by C—H⋯O hydrogen bonds.

Related literature

For the use of proline derivatives in organocatalysis, see: Dalko & Moisan (2004 ). For the synthesis, see: Wiegrebe et al. (1974 ).

Experimental

Crystal data

C₂₁H₃₆N₂O₇
M_r = 428.52
Monoclinic, C 2
a = 21.995 (5) Å
b = 9.9534 (18) Å
c = 10.531 (2) Å
β = 100.631 (3)°
V = 2265.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 93 K
0.43 × 0.40 × 0.33 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: none
9271 measured reflections
2735 independent reflections
2473 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.073
S = 1.00
2735 reflections
280 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2ⁱ	0.99	2.60	3.223 (2)	121
C5—H5A⋯O6ⁱⁱ	0.99	2.50	3.380 (2)	148
C13—H13B⋯O6ⁱⁱⁱ	0.99	2.54	3.231 (2)	127
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+1]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039452/ci2927sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039452/ci2927Isup2.hkl

checkCIF report

Comment top

Proline derivatives are one of the most important catalysts in organocatalysis (Dalko et al., 2004). Here, we report the crystal structure of the title compound.

The asymmetric unit of the title compound consists of one-half each of two crystallographically independent molecules (Fig. 1). The other halves are generated by crystallographic twofold rotational axes. Bond lengths and angles of these two molecules agree with each other and are normal. In one of the independent unit the pyrrolidine ring (N1/C1-C4) adopts a twist conformation whereas in the other the pyrrolidine ring (N2/C12-C15) adopts an envelope conformation.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

Related literature top

For the use of proline derivatives in organocatalysis, see: Dalko & Moisan (2004). For the synthesis, see: Wiegrebe et al. (1974).

Experimental top

The title compound was synthesized according to the method reported in the literature (Wiegrebe et al., 1974). Colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Structure description top

Proline derivatives are one of the most important catalysts in organocatalysis (Dalko et al., 2004). Here, we report the crystal structure of the title compound.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

For the use of proline derivatives in organocatalysis, see: Dalko & Moisan (2004). For the synthesis, see: Wiegrebe et al. (1974).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Views of the two independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Atoms labelled with the suffix A are generated by the symmetry operation (1-x, y, 1-z) in one of the molecules (with atom O1) and (2-x, y, 2-z) on the other (with atom O5).

Bis{[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methyl} carbonate top

Crystal data top

C₂₁H₃₆N₂O₇	F(000) = 928
M_r = 428.52	D_x = 1.256 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3700 reflections
a = 21.995 (5) Å	θ = 3.1–27.5°
b = 9.9534 (18) Å	µ = 0.09 mm⁻¹
c = 10.531 (2) Å	T = 93 K
β = 100.631 (3)°	Block, colourless
V = 2265.9 (8) Å³	0.43 × 0.40 × 0.33 mm
Z = 4

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2473 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 28.5714 pixels mm^-1	h = −28→28
multi–scan	k = −12→10
9271 measured reflections	l = −12→13
2735 independent reflections

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.041P)² + 0.316P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2735 reflections	Δρ_max = 0.20 e Å⁻³
280 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (3)

Crystal data top

C₂₁H₃₆N₂O₇	V = 2265.9 (8) Å³
M_r = 428.52	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 21.995 (5) Å	µ = 0.09 mm⁻¹
b = 9.9534 (18) Å	T = 93 K
c = 10.531 (2) Å	0.43 × 0.40 × 0.33 mm
β = 100.631 (3)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2473 reflections with I > 2σ(I)
9271 measured reflections	R_int = 0.026
2735 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.073	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
2735 reflections	Δρ_min = −0.19 e Å⁻³
280 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	0.61523 (6)	0.82679 (13)	0.77609 (13)	0.0210 (3)
O2	0.70399 (6)	0.83717 (14)	0.92900 (13)	0.0251 (3)
O3	0.54724 (6)	1.15192 (13)	0.54879 (13)	0.0262 (3)
O4	0.5000	0.9521 (2)	0.5000	0.0226 (4)
N1	0.65682 (7)	1.02483 (17)	0.83522 (14)	0.0178 (4)
C1	0.70038 (9)	1.1193 (2)	0.91204 (18)	0.0210 (4)
H1A	0.7435	1.1000	0.9031	0.025*
H1B	0.6973	1.1158	1.0046	0.025*
C2	0.67903 (8)	1.2547 (2)	0.85289 (18)	0.0219 (4)
H2A	0.6978	1.2741	0.7763	0.026*
H2B	0.6894	1.3282	0.9165	0.026*
C3	0.60872 (8)	1.23572 (19)	0.81495 (18)	0.0230 (4)
H3A	0.5885	1.2452	0.8910	0.028*
H3B	0.5905	1.3018	0.7484	0.028*
C4	0.60199 (8)	1.09260 (18)	0.76148 (17)	0.0169 (4)
H4	0.5634	1.0504	0.7804	0.020*
C5	0.60269 (8)	1.0861 (2)	0.61761 (17)	0.0209 (4)
H5A	0.6400	1.1319	0.5987	0.025*
H5B	0.6036	0.9913	0.5896	0.025*
C6	0.5000	1.0718 (3)	0.5000	0.0188 (6)
C7	0.66228 (8)	0.8903 (2)	0.85346 (17)	0.0184 (4)
C8	0.61266 (9)	0.6788 (2)	0.77050 (18)	0.0195 (4)
C9	0.66997 (10)	0.6233 (2)	0.7267 (2)	0.0275 (5)
H9A	0.7063	0.6376	0.7947	0.033*
H9B	0.6759	0.6697	0.6478	0.033*
H9C	0.6646	0.5269	0.7093	0.033*
C10	0.60458 (10)	0.6224 (2)	0.90045 (19)	0.0248 (4)
H10A	0.5703	0.6685	0.9296	0.030*
H10B	0.6427	0.6361	0.9638	0.030*
H10C	0.5956	0.5260	0.8918	0.030*
C11	0.55506 (10)	0.6543 (2)	0.6687 (2)	0.0274 (5)
H11A	0.5596	0.6988	0.5880	0.033*
H11B	0.5188	0.6908	0.6988	0.033*
H11C	0.5496	0.5576	0.6536	0.033*
O5	0.87815 (6)	0.72148 (13)	0.73864 (12)	0.0195 (3)
O6	0.79858 (6)	0.70687 (14)	0.56549 (12)	0.0224 (3)
O7	0.97677 (6)	0.38716 (13)	0.90069 (11)	0.0193 (3)
O8	1.0000	0.5876 (2)	1.0000	0.0284 (5)
N2	0.84043 (7)	0.52083 (17)	0.67249 (14)	0.0172 (4)
C12	0.79789 (8)	0.4284 (2)	0.59120 (17)	0.0198 (4)
H12A	0.7987	0.4419	0.4984	0.024*
H12B	0.7550	0.4393	0.6057	0.024*
C13	0.82406 (10)	0.2922 (2)	0.63755 (19)	0.0240 (5)
H13A	0.8583	0.2659	0.5935	0.029*
H13B	0.7917	0.2219	0.6227	0.029*
C14	0.84733 (9)	0.31487 (19)	0.78185 (18)	0.0235 (4)
H14A	0.8789	0.2471	0.8173	0.028*
H14B	0.8128	0.3104	0.8303	0.028*
C15	0.87548 (7)	0.45583 (18)	0.78907 (16)	0.0156 (3)
H15A	0.8680	0.5033	0.8684	0.019*
C16	0.94416 (7)	0.45378 (19)	0.78534 (16)	0.0183 (4)
H16A	0.9514	0.4052	0.7074	0.022*
H16B	0.9597	0.5468	0.7815	0.022*
C17	1.0000	0.4671 (3)	1.0000	0.0172 (5)
C18	0.83557 (8)	0.6552 (2)	0.65213 (17)	0.0171 (4)
C19	0.88191 (9)	0.8700 (2)	0.73624 (18)	0.0199 (4)
C20	0.93749 (10)	0.8980 (2)	0.84211 (19)	0.0258 (4)
H20A	0.9742	0.8549	0.8201	0.031*
H20B	0.9298	0.8619	0.9243	0.031*
H20C	0.9443	0.9951	0.8502	0.031*
C21	0.89438 (10)	0.9192 (2)	0.60638 (18)	0.0270 (5)
H21A	0.8577	0.9035	0.5395	0.032*
H21B	0.9297	0.8702	0.5844	0.032*
H21C	0.9037	1.0156	0.6117	0.032*
C22	0.82306 (9)	0.9276 (2)	0.7694 (2)	0.0265 (4)
H22A	0.8156	0.8876	0.8502	0.032*
H22B	0.7882	0.9073	0.6997	0.032*
H22C	0.8273	1.0252	0.7798	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (7)	0.0133 (8)	0.0254 (7)	−0.0019 (5)	−0.0034 (5)	0.0023 (5)
O2	0.0217 (7)	0.0242 (9)	0.0260 (7)	0.0008 (6)	−0.0046 (6)	0.0067 (6)
O3	0.0272 (7)	0.0192 (7)	0.0259 (7)	−0.0017 (6)	−0.0118 (6)	0.0039 (6)
O4	0.0231 (9)	0.0178 (12)	0.0262 (10)	0.000	0.0024 (8)	0.000
N1	0.0147 (7)	0.0170 (9)	0.0193 (8)	−0.0025 (6)	−0.0027 (6)	0.0010 (6)
C1	0.0165 (9)	0.0244 (12)	0.0198 (9)	−0.0046 (8)	−0.0027 (7)	0.0003 (8)
C2	0.0190 (9)	0.0201 (11)	0.0242 (10)	−0.0026 (8)	−0.0021 (8)	−0.0018 (8)
C3	0.0189 (8)	0.0226 (10)	0.0259 (9)	0.0026 (8)	0.0000 (7)	−0.0038 (8)
C4	0.0120 (7)	0.0179 (10)	0.0201 (9)	−0.0004 (7)	0.0011 (6)	0.0010 (7)
C5	0.0169 (8)	0.0244 (10)	0.0197 (9)	0.0006 (7)	−0.0011 (7)	0.0013 (7)
C6	0.0212 (12)	0.0211 (16)	0.0131 (12)	0.000	0.0003 (10)	0.000
C7	0.0150 (8)	0.0222 (11)	0.0174 (8)	−0.0016 (8)	0.0011 (7)	0.0006 (8)
C8	0.0225 (9)	0.0136 (10)	0.0208 (10)	−0.0004 (8)	0.0002 (8)	0.0001 (7)
C9	0.0298 (10)	0.0281 (12)	0.0254 (10)	0.0028 (9)	0.0070 (8)	0.0013 (9)
C10	0.0323 (11)	0.0189 (11)	0.0241 (10)	−0.0016 (8)	0.0077 (8)	0.0016 (8)
C11	0.0307 (11)	0.0189 (11)	0.0286 (11)	−0.0009 (9)	−0.0053 (9)	−0.0011 (9)
O5	0.0218 (6)	0.0140 (8)	0.0201 (6)	−0.0001 (5)	−0.0032 (5)	−0.0006 (5)
O6	0.0211 (7)	0.0220 (8)	0.0215 (7)	0.0048 (6)	−0.0028 (6)	0.0028 (6)
O7	0.0184 (6)	0.0175 (7)	0.0187 (6)	0.0002 (5)	−0.0049 (5)	0.0004 (5)
O8	0.0403 (12)	0.0182 (12)	0.0235 (10)	0.000	−0.0028 (9)	0.000
N2	0.0160 (8)	0.0170 (9)	0.0160 (7)	0.0004 (6)	−0.0041 (6)	0.0005 (6)
C12	0.0184 (9)	0.0193 (11)	0.0192 (9)	−0.0021 (8)	−0.0031 (7)	−0.0018 (8)
C13	0.0250 (10)	0.0184 (12)	0.0244 (10)	−0.0052 (8)	−0.0062 (8)	−0.0005 (8)
C14	0.0230 (9)	0.0212 (10)	0.0236 (9)	−0.0057 (8)	−0.0029 (7)	0.0043 (8)
C15	0.0150 (7)	0.0159 (9)	0.0147 (8)	0.0012 (7)	−0.0003 (6)	0.0006 (7)
C16	0.0155 (8)	0.0223 (10)	0.0157 (8)	0.0007 (7)	−0.0008 (6)	0.0010 (7)
C17	0.0122 (11)	0.0201 (16)	0.0189 (12)	0.000	0.0017 (10)	0.000
C18	0.0165 (8)	0.0178 (11)	0.0169 (9)	0.0013 (7)	0.0030 (7)	0.0001 (7)
C19	0.0248 (10)	0.0127 (11)	0.0215 (9)	0.0014 (8)	0.0030 (8)	0.0015 (8)
C20	0.0296 (10)	0.0191 (11)	0.0268 (10)	−0.0037 (8)	−0.0003 (8)	−0.0023 (8)
C21	0.0345 (11)	0.0222 (12)	0.0246 (10)	−0.0019 (9)	0.0065 (9)	0.0017 (8)
C22	0.0286 (10)	0.0189 (11)	0.0331 (10)	0.0022 (8)	0.0086 (9)	−0.0040 (9)

Geometric parameters (Å, º) top

O1—C7	1.350 (2)	O5—C18	1.352 (2)
O1—C8	1.475 (2)	O5—C19	1.482 (2)
O2—C7	1.219 (2)	O6—C18	1.219 (2)
O3—C6	1.335 (2)	O7—C17	1.338 (2)
O3—C5	1.455 (2)	O7—C16	1.4519 (19)
O4—C6	1.191 (4)	O8—C17	1.200 (4)
N1—C7	1.355 (3)	N2—C18	1.355 (3)
N1—C4	1.472 (2)	N2—C12	1.469 (2)
N1—C1	1.473 (2)	N2—C15	1.473 (2)
C1—C2	1.522 (3)	C12—C13	1.518 (3)
C1—H1A	0.99	C12—H12A	0.99
C1—H1B	0.99	C12—H12B	0.99
C2—C3	1.536 (2)	C13—C14	1.528 (3)
C2—H2A	0.99	C13—H13A	0.99
C2—H2B	0.99	C13—H13B	0.99
C3—C4	1.529 (3)	C14—C15	1.530 (3)
C3—H3A	0.99	C14—H14A	0.99
C3—H3B	0.99	C14—H14B	0.99
C4—C5	1.519 (2)	C15—C16	1.518 (2)
C4—H4	1.00	C15—H15A	1.00
C5—H5A	0.99	C16—H16A	0.99
C5—H5B	0.99	C16—H16B	0.99
C6—O3ⁱ	1.335 (2)	C17—O7ⁱⁱ	1.338 (2)
C8—C10	1.520 (3)	C19—C22	1.514 (3)
C8—C11	1.521 (3)	C19—C20	1.520 (3)
C8—C9	1.524 (3)	C19—C21	1.524 (3)
C9—H9A	0.98	C20—H20A	0.98
C9—H9B	0.98	C20—H20B	0.98
C9—H9C	0.98	C20—H20C	0.98
C10—H10A	0.98	C21—H21A	0.98
C10—H10B	0.98	C21—H21B	0.98
C10—H10C	0.98	C21—H21C	0.98
C11—H11A	0.98	C22—H22A	0.98
C11—H11B	0.98	C22—H22B	0.98
C11—H11C	0.98	C22—H22C	0.98

C7—O1—C8	120.75 (16)	C18—O5—C19	120.63 (15)
C6—O3—C5	116.37 (15)	C17—O7—C16	116.16 (15)
C7—N1—C4	124.77 (16)	C18—N2—C12	120.16 (16)
C7—N1—C1	121.41 (17)	C18—N2—C15	125.37 (15)
C4—N1—C1	112.57 (16)	C12—N2—C15	112.93 (15)
N1—C1—C2	102.72 (15)	N2—C12—C13	102.06 (14)
N1—C1—H1A	111.2	N2—C12—H12A	111.4
C2—C1—H1A	111.2	C13—C12—H12A	111.4
N1—C1—H1B	111.2	N2—C12—H12B	111.4
C2—C1—H1B	111.2	C13—C12—H12B	111.4
H1A—C1—H1B	109.1	H12A—C12—H12B	109.2
C1—C2—C3	102.54 (16)	C12—C13—C14	103.02 (16)
C1—C2—H2A	111.3	C12—C13—H13A	111.2
C3—C2—H2A	111.3	C14—C13—H13A	111.2
C1—C2—H2B	111.3	C12—C13—H13B	111.2
C3—C2—H2B	111.3	C14—C13—H13B	111.2
H2A—C2—H2B	109.2	H13A—C13—H13B	109.1
C4—C3—C2	103.59 (15)	C13—C14—C15	104.08 (15)
C4—C3—H3A	111.0	C13—C14—H14A	110.9
C2—C3—H3A	111.0	C15—C14—H14A	110.9
C4—C3—H3B	111.0	C13—C14—H14B	110.9
C2—C3—H3B	111.0	C15—C14—H14B	110.9
H3A—C3—H3B	109.0	H14A—C14—H14B	109.0
N1—C4—C5	110.40 (14)	N2—C15—C16	110.76 (13)
N1—C4—C3	102.62 (14)	N2—C15—C14	102.50 (14)
C5—C4—C3	112.86 (15)	C16—C15—C14	112.45 (15)
N1—C4—H4	110.2	N2—C15—H15A	110.3
C5—C4—H4	110.2	C16—C15—H15A	110.3
C3—C4—H4	110.2	C14—C15—H15A	110.3
O3—C5—C4	108.41 (14)	O7—C16—C15	108.95 (13)
O3—C5—H5A	110.0	O7—C16—H16A	109.9
C4—C5—H5A	110.0	C15—C16—H16A	109.9
O3—C5—H5B	110.0	O7—C16—H16B	109.9
C4—C5—H5B	110.0	C15—C16—H16B	109.9
H5A—C5—H5B	108.4	H16A—C16—H16B	108.3
O4—C6—O3ⁱ	126.69 (12)	O8—C17—O7	126.48 (11)
O4—C6—O3	126.69 (12)	O8—C17—O7ⁱⁱ	126.48 (11)
O3ⁱ—C6—O3	106.6 (2)	O7—C17—O7ⁱⁱ	107.0 (2)
O2—C7—O1	126.3 (2)	O6—C18—O5	125.61 (19)
O2—C7—N1	123.91 (19)	O6—C18—N2	123.86 (19)
O1—C7—N1	109.83 (16)	O5—C18—N2	110.51 (16)
O1—C8—C10	110.09 (16)	O5—C19—C22	108.72 (16)
O1—C8—C11	102.07 (16)	O5—C19—C20	102.10 (15)
C10—C8—C11	110.79 (17)	C22—C19—C20	111.57 (16)
O1—C8—C9	110.27 (16)	O5—C19—C21	110.84 (16)
C10—C8—C9	112.29 (17)	C22—C19—C21	112.85 (17)
C11—C8—C9	110.88 (16)	C20—C19—C21	110.23 (17)
C8—C9—H9A	109.5	C19—C20—H20A	109.5
C8—C9—H9B	109.5	C19—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C8—C9—H9C	109.5	C19—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
C8—C10—H10A	109.5	C19—C21—H21A	109.5
C8—C10—H10B	109.5	C19—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
C8—C10—H10C	109.5	C19—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
C8—C11—H11A	109.5	C19—C22—H22A	109.5
C8—C11—H11B	109.5	C19—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C8—C11—H11C	109.5	C19—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5

C7—N1—C1—C2	176.45 (17)	C18—N2—C12—C13	174.22 (16)
C4—N1—C1—C2	−15.76 (19)	C15—N2—C12—C13	−19.19 (18)
N1—C1—C2—C3	33.84 (18)	N2—C12—C13—C14	35.11 (18)
C1—C2—C3—C4	−40.29 (18)	C12—C13—C14—C15	−39.24 (19)
C7—N1—C4—C5	−81.3 (2)	C18—N2—C15—C16	−78.9 (2)
C1—N1—C4—C5	111.38 (17)	C12—N2—C15—C16	115.30 (16)
C7—N1—C4—C3	158.15 (17)	C18—N2—C15—C14	160.90 (17)
C1—N1—C4—C3	−9.15 (19)	C12—N2—C15—C14	−4.86 (18)
C2—C3—C4—N1	30.20 (18)	C13—C14—C15—N2	26.95 (18)
C2—C3—C4—C5	−88.61 (17)	C13—C14—C15—C16	−92.03 (17)
C6—O3—C5—C4	−98.00 (16)	C17—O7—C16—C15	−94.52 (15)
N1—C4—C5—O3	178.94 (14)	N2—C15—C16—O7	−179.11 (14)
C3—C4—C5—O3	−66.87 (18)	C14—C15—C16—O7	−65.08 (18)
C5—O3—C6—O4	−5.10 (16)	C16—O7—C17—O8	−5.21 (14)
C5—O3—C6—O3ⁱ	174.90 (16)	C16—O7—C17—O7ⁱⁱ	174.79 (14)
C8—O1—C7—O2	−4.2 (3)	C19—O5—C18—O6	1.8 (3)
C8—O1—C7—N1	175.71 (15)	C19—O5—C18—N2	−179.82 (14)
C4—N1—C7—O2	−169.34 (17)	C12—N2—C18—O6	−2.7 (3)
C1—N1—C7—O2	−3.1 (3)	C15—N2—C18—O6	−167.50 (16)
C4—N1—C7—O1	10.8 (3)	C12—N2—C18—O5	178.84 (14)
C1—N1—C7—O1	176.99 (15)	C15—N2—C18—O5	14.0 (2)
C7—O1—C8—C10	64.9 (2)	C18—O5—C19—C22	65.4 (2)
C7—O1—C8—C11	−177.36 (15)	C18—O5—C19—C20	−176.56 (15)
C7—O1—C8—C9	−59.5 (2)	C18—O5—C19—C21	−59.2 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱⁱⁱ	0.99	2.60	3.223 (2)	121
C5—H5A···O6^iv	0.99	2.50	3.380 (2)	148
C13—H13B···O6^v	0.99	2.54	3.231 (2)	127

Symmetry codes: (iii) −x+3/2, y+1/2, −z+2; (iv) −x+3/2, y+1/2, −z+1; (v) −x+3/2, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₆N₂O₇
M_r	428.52
Crystal system, space group	Monoclinic, C2
Temperature (K)	93
a, b, c (Å)	21.995 (5), 9.9534 (18), 10.531 (2)
β (°)	100.631 (3)
V (Å³)	2265.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.40 × 0.33

Data collection
Diffractometer	Rigaku AFC10/Saturn724+
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9271, 2735, 2473
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.073, 1.00
No. of reflections	2735
No. of parameters	280
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.99	2.60	3.223 (2)	121
C5—H5A···O6ⁱⁱ	0.99	2.50	3.380 (2)	148
C13—H13B···O6ⁱⁱⁱ	0.99	2.54	3.231 (2)	127

Symmetry codes: (i) −x+3/2, y+1/2, −z+2; (ii) −x+3/2, y+1/2, −z+1; (iii) −x+3/2, y−1/2, −z+1.

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Dalko, P. I. & Moisan, L. (2004). Angew. Chem. Int. Ed. 43, 5138–5175. Web of Science CrossRef CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wiegrebe, W., Herrmann, E. G., Schlunegger, U. P. & Budzikiewicz, H. (1974). Helv. Chim. Acta, 57, 301–314. CrossRef CAS PubMed Web of Science Google Scholar