(4R,5S)-Methyl 1,3-dibenzyl-5-[(R)-2-(hydroxy­diphenyl­meth­yl)pyrrolidine-1-carbon­yl]-2-oxoimidazolidine-4-carboxyl­ate

Liu, J.; Chen, F.-E.; Chen, M.-Q.

doi:10.1107/S1600536807045874

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(4R,5S)-Methyl 1,3-dibenzyl-5-[(R)-2-(hydroxydiphenylmethyl)pyrrolidine-1-carbonyl]-2-oxoimidazolidine-4-carboxylate

J. Liu, F.-E. Chen and M.-Q. Chen

The title compound, C₃₇H₃₇N₃O₅, was synthesized as a key intermediate in the total synthesis of d-biotin and was crystallized from 2-propanol. It contains one chiral center in the pyrrole ring, where the absolute configuration is known from the synthesis, and from which the two other chiral centers in the imidazolidine ring could be determined. An intramolecular O—H

O and intermolecular C—H

O hydrogen bonds help to construct the three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045874/ez2097sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045874/ez2097Isup2.hkl Contains datablock I

CCDC reference: 663814

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.042
wR factor = 0.111
Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        400 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.29 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       5.02 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C31    -   C32     ..       6.48 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C32
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C14    -C19           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16    ..  O4      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  O5      ..       2.80 Ang.

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           27.18
           From the CIF: _reflns_number_total               3679
           Count of symmetry unique reflns         3722
           Completeness (_total/calc)             98.84%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In our ongoing research on the total synthesis of d-biotin, an efficient and highly diastereoselective approach was developed with (4R,5S)-methyl 1,3-dibenzyl-5- ((R)-2-(hydroxydiphenylmethyl)pyrrolidine-1-carbonyl)-2- oxoimidazolidine-4-carboxylate(I) prepared as a key intermediate. Determination of the three-dimensional structure would help us to investigate the absolute configurations of the three chiral centers. Herein, we report the crystal structure of the title compound (I).

Fig. 1 shows the molecular structure of (I). Due to the certainty of C24 being R-configuration, based on the synthesis, the diffraction analysis indicates that the two other chiral carbon atoms (C4 and C5) have R– and S-configurations respectively. The strong O5—H5X···O4 intramolecular hydrogen bond may enhance the molecular stability of this compound. Intermolecular C—H···O hydrogen bonds lead to a three-dimensional network.

Related literature top

Please provide reference(s) to some related literature.

Experimental top

To a solution of (4R,5S)-1,3-dibenzyl-5-((R)-2-(hydroxydiphenylmethyl) pyrrolidine-1-carbonyl)-2- oxoimidazolidine-4-carboxylic acid (8 g, 13.68 mmol) in acetone (100 ml) was added NaOH (1.13 g, 27.36 mmol). After stirring at r.t. for 2 h, Me₂SO₄ (2.57 ml, 27.36 mmol) was added, followed by a catalytic amount of Bu₄NI. Then the reaction mixture was heated under reflux for 10 h. The solvent was evaporated in vacuo, 5% aq NH₄Cl (50 ml) was added and extracted with CH₂Cl₂. The combined organic layers were washed with 5% aq NaHCO₃ (50 ml), H₂O (50 ml) and brine (50 ml), and dried (MgSO₄). Evaporation of the solvent under reduced pressure gave the crude product, which was washed with Et₂O to afford a white powder (6.4 g, 78%), m.p. 444 K. Recrystallization from 2-propanol yielded colorless crystals of the title compound suitable for X-ray diffraction.

Structure description top

Please provide reference(s) to some related literature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

	Fig. 1. Molecular structure of the title compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are indicated by dashed lines.
	Fig. 2. The formation of the title compound.

(4R,5S)-Methyl 1,3-dibenzyl-5-[(R)-2-(hydroxydiphenylmethyl)pyrrolidine-1-carbonyl]- 2-oxoimidazolidine-4-carboxylate top

Crystal data top

C₃₇H₃₇N₃O₅	F(000) = 640
M_r = 603.70	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 793 reflections
a = 12.075 (4) Å	θ = 2.5–21.2°
b = 10.907 (4) Å	µ = 0.08 mm⁻¹
c = 12.328 (4) Å	T = 293 K
β = 101.396 (5)°	Prism, colorless
V = 1591.5 (10) Å³	0.20 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3679 independent reflections
Radiation source: fine-focus sealed tube	2645 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 27.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→15
T_min = 0.983, T_max = 0.992	k = −13→13
8080 measured reflections	l = −15→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0606P)²] where P = (F_o² + 2F_c²)/3
3679 reflections	(Δ/σ)_max < 0.001
411 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₃₇H₃₇N₃O₅	V = 1591.5 (10) Å³
M_r = 603.70	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 12.075 (4) Å	µ = 0.08 mm⁻¹
b = 10.907 (4) Å	T = 293 K
c = 12.328 (4) Å	0.20 × 0.12 × 0.10 mm
β = 101.396 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3679 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2645 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.992	R_int = 0.029
8080 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.13 e Å⁻³
3679 reflections	Δρ_min = −0.13 e Å⁻³
411 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	0.01834 (19)	0.4307 (2)	−0.02044 (17)	0.0663 (6)
O2	−0.23633 (19)	0.5563 (3)	0.19449 (19)	0.0850 (7)
O3	−0.16338 (16)	0.7314 (2)	0.27063 (17)	0.0651 (5)
O4	0.03920 (15)	0.54484 (17)	0.32417 (14)	0.0531 (4)
O5	0.24961 (16)	0.56160 (19)	0.46064 (15)	0.0568 (5)
H5X	0.1866 (18)	0.535 (3)	0.432 (2)	0.064 (10)*
N1	0.07821 (18)	0.5786 (2)	0.11061 (18)	0.0528 (5)
C2	0.0000 (2)	0.5168 (3)	0.0374 (2)	0.0494 (6)
N3	−0.10202 (19)	0.5674 (2)	0.03674 (18)	0.0563 (6)
C4	−0.0978 (2)	0.6659 (3)	0.1152 (2)	0.0485 (6)
H4	−0.1218	0.7420	0.0752	0.058*
C5	0.03034 (19)	0.6750 (2)	0.16817 (19)	0.0456 (6)
H5	0.0605	0.7551	0.1527	0.055*
C6	0.1946 (2)	0.5416 (3)	0.1395 (2)	0.0644 (8)
H6A	0.2011	0.4594	0.1113	0.077*
H6B	0.2160	0.5376	0.2195	0.077*
C7	0.2781 (2)	0.6236 (4)	0.0971 (2)	0.0673 (9)
C8	0.3910 (3)	0.5966 (7)	0.1312 (3)	0.120 (2)
H8	0.4132	0.5337	0.1817	0.144*
C9	0.4715 (4)	0.6629 (10)	0.0905 (5)	0.151 (3)
H9	0.5478	0.6470	0.1159	0.181*
C10	0.4386 (6)	0.7515 (7)	0.0132 (6)	0.145 (3)
H10	0.4931	0.7932	−0.0161	0.174*
C11	0.3266 (5)	0.7808 (4)	−0.0226 (4)	0.1065 (15)
H11	0.3046	0.8425	−0.0745	0.128*
C12	0.2469 (3)	0.7147 (3)	0.0215 (3)	0.0752 (9)
H12	0.1707	0.7333	−0.0012	0.090*
C13	−0.1988 (2)	0.5433 (3)	−0.0507 (2)	0.0642 (8)
H13A	−0.2667	0.5504	−0.0202	0.077*
H13B	−0.1943	0.4593	−0.0753	0.077*
C14	−0.2106 (2)	0.6261 (3)	−0.1498 (2)	0.0553 (7)
C15	−0.1246 (3)	0.6958 (3)	−0.1739 (3)	0.0680 (8)
H15	−0.0548	0.6953	−0.1259	0.082*
C16	−0.1398 (4)	0.7672 (3)	−0.2687 (3)	0.0838 (11)
H16	−0.0810	0.8153	−0.2836	0.101*
C17	−0.2416 (5)	0.7661 (4)	−0.3396 (3)	0.1025 (14)
H17	−0.2527	0.8137	−0.4035	0.123*
C18	−0.3259 (5)	0.6967 (6)	−0.3174 (4)	0.136 (2)
H18	−0.3951	0.6958	−0.3664	0.163*
C19	−0.3110 (4)	0.6273 (4)	−0.2236 (4)	0.1092 (16)
H19	−0.3705	0.5798	−0.2097	0.131*
C20	−0.1737 (2)	0.6415 (3)	0.1980 (2)	0.0556 (7)
C21	−0.2295 (3)	0.7239 (5)	0.3560 (3)	0.0907 (12)
H21A	−0.1970	0.6637	0.4098	0.136*
H21B	−0.3055	0.7007	0.3237	0.136*
H21C	−0.2298	0.8022	0.3914	0.136*
C22	0.05575 (19)	0.6489 (2)	0.2923 (2)	0.0435 (6)
N23	0.09866 (16)	0.7391 (2)	0.36102 (17)	0.0465 (5)
C24	0.1154 (2)	0.7207 (3)	0.4816 (2)	0.0496 (6)
H24	0.0571	0.6641	0.4965	0.060*
C25	0.0911 (3)	0.8475 (3)	0.5232 (3)	0.0693 (9)
H25A	0.1362	0.8622	0.5964	0.083*
H25B	0.0119	0.8555	0.5266	0.083*
C26	0.1229 (3)	0.9373 (3)	0.4395 (3)	0.0792 (10)
H26A	0.0771	1.0108	0.4350	0.095*
H26B	0.2019	0.9602	0.4603	0.095*
C27	0.1008 (3)	0.8700 (3)	0.3306 (3)	0.0633 (8)
H27A	0.0291	0.8948	0.2856	0.076*
H27B	0.1603	0.8859	0.2899	0.076*
C28	0.2328 (2)	0.6636 (3)	0.5283 (2)	0.0471 (6)
C29	0.3256 (2)	0.7552 (3)	0.5229 (2)	0.0548 (7)
C30	0.3740 (2)	0.7603 (4)	0.4306 (3)	0.0726 (9)
H30	0.3523	0.7048	0.3731	0.087*
C31	0.4557 (3)	0.8490 (5)	0.4238 (4)	0.1074 (15)
H31	0.4884	0.8525	0.3616	0.129*
C32	0.4875 (4)	0.9301 (6)	0.5076 (6)	0.130 (2)
H32	0.5432	0.9876	0.5031	0.156*
C33	0.4378 (4)	0.9283 (4)	0.5999 (4)	0.1076 (15)
H33	0.4570	0.9867	0.6554	0.129*
C34	0.3595 (3)	0.8387 (3)	0.6081 (3)	0.0752 (10)
H34	0.3289	0.8340	0.6715	0.090*
C35	0.2425 (2)	0.6118 (3)	0.6452 (2)	0.0516 (7)
C36	0.1531 (3)	0.6007 (3)	0.6997 (2)	0.0658 (9)
H36	0.0834	0.6351	0.6696	0.079*
C37	0.1683 (4)	0.5377 (4)	0.8000 (3)	0.0817 (11)
H37	0.1077	0.5297	0.8357	0.098*
C38	0.2689 (4)	0.4881 (3)	0.8464 (3)	0.0838 (11)
H38	0.2769	0.4454	0.9128	0.101*
C39	0.3598 (3)	0.5011 (4)	0.7949 (3)	0.0831 (10)
H39	0.4299	0.4685	0.8267	0.100*
C40	0.3455 (3)	0.5627 (3)	0.6962 (3)	0.0706 (8)
H40	0.4072	0.5718	0.6621	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0971 (15)	0.0533 (11)	0.0537 (12)	−0.0013 (11)	0.0272 (10)	−0.0088 (11)
O2	0.0767 (14)	0.106 (2)	0.0775 (15)	−0.0347 (15)	0.0281 (11)	−0.0103 (14)
O3	0.0695 (12)	0.0692 (13)	0.0625 (12)	0.0099 (11)	0.0273 (9)	−0.0043 (12)
O4	0.0664 (11)	0.0444 (11)	0.0489 (10)	−0.0070 (9)	0.0123 (8)	0.0011 (9)
O5	0.0564 (11)	0.0635 (12)	0.0511 (10)	0.0091 (10)	0.0119 (9)	−0.0118 (10)
N1	0.0516 (11)	0.0598 (14)	0.0484 (12)	0.0059 (10)	0.0132 (9)	−0.0049 (11)
C2	0.0643 (16)	0.0521 (16)	0.0343 (13)	−0.0061 (13)	0.0157 (12)	0.0027 (13)
N3	0.0583 (13)	0.0635 (15)	0.0456 (12)	−0.0017 (12)	0.0065 (9)	−0.0038 (11)
C4	0.0532 (14)	0.0468 (14)	0.0451 (14)	0.0035 (12)	0.0088 (11)	0.0043 (12)
C5	0.0517 (13)	0.0424 (14)	0.0447 (14)	−0.0008 (11)	0.0145 (11)	0.0011 (11)
C6	0.0613 (16)	0.080 (2)	0.0540 (16)	0.0163 (16)	0.0176 (12)	0.0009 (16)
C7	0.0549 (15)	0.094 (2)	0.0537 (17)	−0.0020 (16)	0.0129 (13)	−0.0258 (18)
C8	0.059 (2)	0.214 (6)	0.084 (3)	0.000 (3)	0.0053 (18)	−0.009 (3)
C9	0.058 (2)	0.269 (9)	0.125 (4)	−0.015 (4)	0.016 (3)	−0.028 (5)
C10	0.110 (4)	0.177 (7)	0.166 (6)	−0.068 (4)	0.074 (4)	−0.073 (5)
C11	0.134 (4)	0.076 (3)	0.131 (4)	−0.022 (3)	0.078 (3)	−0.026 (3)
C12	0.078 (2)	0.066 (2)	0.091 (2)	−0.0051 (17)	0.0397 (18)	−0.014 (2)
C13	0.0658 (17)	0.073 (2)	0.0515 (15)	−0.0191 (16)	0.0059 (13)	−0.0018 (16)
C14	0.0603 (15)	0.0552 (17)	0.0482 (15)	−0.0049 (13)	0.0051 (12)	−0.0015 (13)
C15	0.0721 (19)	0.070 (2)	0.0630 (18)	0.0012 (15)	0.0174 (15)	0.0069 (16)
C16	0.116 (3)	0.065 (2)	0.081 (2)	0.006 (2)	0.045 (2)	0.0091 (19)
C17	0.159 (4)	0.080 (3)	0.060 (2)	0.008 (3)	0.001 (3)	0.014 (2)
C18	0.125 (4)	0.142 (5)	0.113 (4)	−0.033 (4)	−0.044 (3)	0.052 (4)
C19	0.092 (3)	0.116 (3)	0.102 (3)	−0.031 (3)	−0.025 (2)	0.035 (3)
C20	0.0508 (14)	0.0655 (19)	0.0503 (16)	0.0021 (14)	0.0093 (11)	0.0036 (14)
C21	0.090 (2)	0.118 (3)	0.075 (2)	0.020 (2)	0.0433 (18)	−0.005 (2)
C22	0.0414 (12)	0.0437 (16)	0.0470 (14)	−0.0007 (11)	0.0126 (10)	−0.0006 (12)
N23	0.0476 (11)	0.0422 (12)	0.0491 (12)	0.0006 (9)	0.0083 (9)	−0.0042 (10)
C24	0.0499 (13)	0.0555 (16)	0.0460 (14)	−0.0032 (12)	0.0155 (11)	−0.0104 (13)
C25	0.0664 (18)	0.073 (2)	0.067 (2)	0.0124 (16)	0.0112 (15)	−0.0271 (18)
C26	0.092 (2)	0.0491 (18)	0.088 (3)	0.0115 (17)	−0.0027 (19)	−0.0128 (18)
C27	0.0743 (19)	0.0384 (15)	0.073 (2)	0.0020 (13)	0.0058 (16)	−0.0025 (14)
C28	0.0484 (13)	0.0523 (15)	0.0419 (13)	−0.0010 (12)	0.0122 (10)	−0.0043 (12)
C29	0.0455 (13)	0.0647 (19)	0.0527 (15)	−0.0017 (13)	0.0058 (11)	0.0128 (14)
C30	0.0514 (15)	0.096 (3)	0.0727 (19)	−0.0014 (16)	0.0182 (13)	0.0189 (19)
C31	0.073 (2)	0.140 (4)	0.112 (3)	−0.023 (3)	0.026 (2)	0.042 (3)
C32	0.074 (3)	0.154 (5)	0.148 (4)	−0.053 (3)	−0.013 (3)	0.064 (4)
C33	0.106 (3)	0.094 (3)	0.103 (3)	−0.043 (3)	−0.030 (3)	0.017 (3)
C34	0.072 (2)	0.077 (2)	0.068 (2)	−0.0200 (18)	−0.0070 (16)	0.0021 (18)
C35	0.0585 (16)	0.0525 (16)	0.0451 (14)	−0.0079 (12)	0.0137 (12)	−0.0065 (13)
C36	0.0645 (17)	0.087 (2)	0.0488 (16)	−0.0235 (16)	0.0178 (13)	−0.0123 (16)
C37	0.107 (3)	0.096 (3)	0.0486 (17)	−0.044 (2)	0.0316 (18)	−0.0157 (19)
C38	0.132 (4)	0.070 (2)	0.0475 (18)	−0.019 (2)	0.014 (2)	−0.0023 (17)
C39	0.112 (3)	0.079 (2)	0.0565 (19)	0.020 (2)	0.0122 (19)	0.0123 (18)
C40	0.079 (2)	0.077 (2)	0.0581 (17)	0.0140 (17)	0.0210 (15)	0.0108 (17)

Geometric parameters (Å, º) top

O1—C2	1.225 (3)	C18—H18	0.9300
O2—C20	1.194 (4)	C19—H19	0.9300
O3—C20	1.317 (4)	C21—H21A	0.9599
O3—C21	1.443 (4)	C21—H21B	0.9599
O4—C22	1.230 (3)	C21—H21C	0.9599
O5—C28	1.429 (3)	C22—N23	1.335 (3)
O5—H5X	0.825 (18)	N23—C24	1.473 (3)
N1—C2	1.350 (3)	N23—C27	1.477 (4)
N1—C6	1.438 (4)	C24—C25	1.524 (4)
N1—C5	1.451 (3)	C24—C28	1.552 (4)
C2—N3	1.348 (4)	C24—H24	0.9800
N3—C4	1.439 (4)	C25—C26	1.526 (5)
N3—C13	1.449 (4)	C25—H25A	0.9700
C4—C20	1.524 (4)	C25—H25B	0.9700
C4—C5	1.559 (3)	C26—C27	1.506 (5)
C4—H4	0.9800	C26—H26A	0.9700
C5—C22	1.527 (3)	C26—H26B	0.9700
C5—H5	0.9800	C27—H27A	0.9700
C6—C7	1.516 (5)	C27—H27B	0.9700
C6—H6A	0.9700	C28—C29	1.513 (4)
C6—H6B	0.9700	C28—C35	1.531 (4)
C7—C12	1.364 (5)	C29—C30	1.379 (4)
C7—C8	1.377 (5)	C29—C34	1.389 (4)
C8—C9	1.383 (9)	C30—C31	1.396 (6)
C8—H8	0.9300	C30—H30	0.9300
C9—C10	1.360 (10)	C31—C32	1.357 (8)
C9—H9	0.9300	C31—H31	0.9300
C10—C11	1.375 (9)	C32—C33	1.387 (8)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.395 (5)	C33—C34	1.377 (5)
C11—H11	0.9300	C33—H33	0.9300
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.503 (4)	C35—C36	1.384 (4)
C13—H13A	0.9700	C35—C40	1.386 (4)
C13—H13B	0.9700	C36—C37	1.395 (5)
C14—C19	1.364 (5)	C36—H36	0.9300
C14—C15	1.365 (4)	C37—C38	1.349 (6)
C15—C16	1.386 (5)	C37—H37	0.9300
C15—H15	0.9300	C38—C39	1.380 (6)
C16—C17	1.360 (6)	C38—H38	0.9300
C16—H16	0.9300	C39—C40	1.371 (5)
C17—C18	1.339 (7)	C39—H39	0.9300
C17—H17	0.9300	C40—H40	0.9300
C18—C19	1.364 (6)

C20—O3—C21	117.5 (3)	H21A—C21—H21B	109.5
C28—O5—H5X	107 (2)	O3—C21—H21C	109.5
C2—N1—C6	123.1 (2)	H21A—C21—H21C	109.5
C2—N1—C5	113.3 (2)	H21B—C21—H21C	109.5
C6—N1—C5	123.2 (2)	O4—C22—N23	123.1 (2)
O1—C2—N3	125.4 (2)	O4—C22—C5	118.6 (2)
O1—C2—N1	126.0 (2)	N23—C22—C5	118.3 (2)
N3—C2—N1	108.5 (2)	C22—N23—C24	119.8 (2)
C2—N3—C4	113.0 (2)	C22—N23—C27	125.2 (2)
C2—N3—C13	122.2 (2)	C24—N23—C27	112.5 (2)
C4—N3—C13	123.4 (2)	N23—C24—C25	102.6 (2)
N3—C4—C20	111.9 (2)	N23—C24—C28	111.25 (19)
N3—C4—C5	103.27 (19)	C25—C24—C28	117.5 (2)
C20—C4—C5	114.1 (2)	N23—C24—H24	108.4
N3—C4—H4	109.1	C25—C24—H24	108.4
C20—C4—H4	109.1	C28—C24—H24	108.4
C5—C4—H4	109.1	C24—C25—C26	105.3 (2)
N1—C5—C22	109.6 (2)	C24—C25—H25A	110.7
N1—C5—C4	101.96 (19)	C26—C25—H25A	110.7
C22—C5—C4	113.22 (18)	C24—C25—H25B	110.7
N1—C5—H5	110.6	C26—C25—H25B	110.7
C22—C5—H5	110.6	H25A—C25—H25B	108.8
C4—C5—H5	110.6	C27—C26—C25	105.5 (3)
N1—C6—C7	115.6 (3)	C27—C26—H26A	110.7
N1—C6—H6A	108.4	C25—C26—H26A	110.7
C7—C6—H6A	108.4	C27—C26—H26B	110.7
N1—C6—H6B	108.4	C25—C26—H26B	110.7
C7—C6—H6B	108.4	H26A—C26—H26B	108.8
H6A—C6—H6B	107.4	N23—C27—C26	104.7 (3)
C12—C7—C8	119.1 (4)	N23—C27—H27A	110.8
C12—C7—C6	123.6 (3)	C26—C27—H27A	110.8
C8—C7—C6	117.0 (4)	N23—C27—H27B	110.8
C7—C8—C9	120.1 (6)	C26—C27—H27B	110.8
C7—C8—H8	119.9	H27A—C27—H27B	108.9
C9—C8—H8	119.9	O5—C28—C29	107.3 (2)
C10—C9—C8	119.8 (5)	O5—C28—C35	105.6 (2)
C10—C9—H9	120.1	C29—C28—C35	111.5 (2)
C8—C9—H9	120.1	O5—C28—C24	108.7 (2)
C9—C10—C11	121.5 (5)	C29—C28—C24	110.4 (2)
C9—C10—H10	119.3	C35—C28—C24	113.04 (19)
C11—C10—H10	119.3	C30—C29—C34	119.2 (3)
C10—C11—C12	117.7 (5)	C30—C29—C28	120.1 (3)
C10—C11—H11	121.2	C34—C29—C28	120.7 (3)
C12—C11—H11	121.2	C29—C30—C31	119.8 (4)
C7—C12—C11	121.7 (4)	C29—C30—H30	120.1
C7—C12—H12	119.2	C31—C30—H30	120.1
C11—C12—H12	119.2	C32—C31—C30	120.2 (4)
N3—C13—C14	115.4 (2)	C32—C31—H31	119.9
N3—C13—H13A	108.4	C30—C31—H31	119.9
C14—C13—H13A	108.4	C31—C32—C33	120.8 (4)
N3—C13—H13B	108.4	C31—C32—H32	119.6
C14—C13—H13B	108.4	C33—C32—H32	119.6
H13A—C13—H13B	107.5	C34—C33—C32	119.0 (5)
C19—C14—C15	117.6 (3)	C34—C33—H33	120.5
C19—C14—C13	118.5 (3)	C32—C33—H33	120.5
C15—C14—C13	123.9 (3)	C33—C34—C29	120.9 (4)
C14—C15—C16	121.1 (3)	C33—C34—H34	119.5
C14—C15—H15	119.4	C29—C34—H34	119.5
C16—C15—H15	119.4	C36—C35—C40	117.5 (3)
C17—C16—C15	119.3 (4)	C36—C35—C28	124.6 (2)
C17—C16—H16	120.3	C40—C35—C28	117.6 (2)
C15—C16—H16	120.3	C35—C36—C37	119.7 (3)
C18—C17—C16	120.0 (4)	C35—C36—H36	120.2
C18—C17—H17	120.0	C37—C36—H36	120.2
C16—C17—H17	120.0	C38—C37—C36	121.6 (3)
C17—C18—C19	120.6 (4)	C38—C37—H37	119.2
C17—C18—H18	119.7	C36—C37—H37	119.2
C19—C18—H18	119.7	C37—C38—C39	119.6 (3)
C14—C19—C18	121.4 (4)	C37—C38—H38	120.2
C14—C19—H19	119.3	C39—C38—H38	120.2
C18—C19—H19	119.3	C40—C39—C38	119.1 (4)
O2—C20—O3	125.3 (3)	C40—C39—H39	120.4
O2—C20—C4	124.9 (3)	C38—C39—H39	120.4
O3—C20—C4	109.7 (3)	C39—C40—C35	122.5 (3)
O3—C21—H21A	109.5	C39—C40—H40	118.8
O3—C21—H21B	109.5	C35—C40—H40	118.8

C6—N1—C2—O1	−7.2 (4)	C4—C5—C22—O4	66.3 (3)
C5—N1—C2—O1	−179.1 (2)	N1—C5—C22—N23	131.0 (2)
C6—N1—C2—N3	174.1 (2)	C4—C5—C22—N23	−116.0 (2)
C5—N1—C2—N3	2.2 (3)	O4—C22—N23—C24	−7.5 (3)
O1—C2—N3—C4	178.9 (2)	C5—C22—N23—C24	174.9 (2)
N1—C2—N3—C4	−2.3 (3)	O4—C22—N23—C27	−168.1 (3)
O1—C2—N3—C13	−14.3 (4)	C5—C22—N23—C27	14.4 (3)
N1—C2—N3—C13	164.5 (2)	C22—N23—C24—C25	−145.6 (2)
C2—N3—C4—C20	−121.7 (2)	C27—N23—C24—C25	17.3 (3)
C13—N3—C4—C20	71.7 (3)	C22—N23—C24—C28	88.0 (3)
C2—N3—C4—C5	1.5 (3)	C27—N23—C24—C28	−109.2 (3)
C13—N3—C4—C5	−165.1 (2)	N23—C24—C25—C26	−28.8 (3)
C2—N1—C5—C22	119.0 (2)	C28—C24—C25—C26	93.6 (3)
C6—N1—C5—C22	−52.8 (3)	C24—C25—C26—C27	30.6 (3)
C2—N1—C5—C4	−1.2 (3)	C22—N23—C27—C26	163.1 (2)
C6—N1—C5—C4	−173.0 (2)	C24—N23—C27—C26	1.3 (3)
N3—C4—C5—N1	−0.2 (2)	C25—C26—C27—N23	−19.6 (3)
C20—C4—C5—N1	121.5 (2)	N23—C24—C28—O5	−47.9 (3)
N3—C4—C5—C22	−117.8 (2)	C25—C24—C28—O5	−165.8 (2)
C20—C4—C5—C22	3.9 (3)	N23—C24—C28—C29	69.5 (3)
C2—N1—C6—C7	109.6 (3)	C25—C24—C28—C29	−48.4 (3)
C5—N1—C6—C7	−79.4 (3)	N23—C24—C28—C35	−164.9 (2)
N1—C6—C7—C12	−10.7 (4)	C25—C24—C28—C35	77.3 (3)
N1—C6—C7—C8	174.6 (3)	O5—C28—C29—C30	27.7 (3)
C12—C7—C8—C9	1.2 (7)	C35—C28—C29—C30	142.9 (3)
C6—C7—C8—C9	176.1 (5)	C24—C28—C29—C30	−90.5 (3)
C7—C8—C9—C10	−2.7 (10)	O5—C28—C29—C34	−155.2 (2)
C8—C9—C10—C11	2.8 (10)	C35—C28—C29—C34	−40.0 (3)
C9—C10—C11—C12	−1.2 (8)	C24—C28—C29—C34	86.5 (3)
C8—C7—C12—C11	0.4 (5)	C34—C29—C30—C31	−0.2 (5)
C6—C7—C12—C11	−174.2 (3)	C28—C29—C30—C31	176.9 (3)
C10—C11—C12—C7	−0.4 (6)	C29—C30—C31—C32	0.0 (6)
C2—N3—C13—C14	−87.1 (3)	C30—C31—C32—C33	−1.5 (7)
C4—N3—C13—C14	78.2 (4)	C31—C32—C33—C34	3.3 (7)
N3—C13—C14—C19	−165.8 (4)	C32—C33—C34—C29	−3.6 (6)
N3—C13—C14—C15	17.9 (4)	C30—C29—C34—C33	2.0 (5)
C19—C14—C15—C16	1.4 (5)	C28—C29—C34—C33	−175.0 (3)
C13—C14—C15—C16	177.8 (3)	O5—C28—C35—C36	−110.4 (3)
C14—C15—C16—C17	−1.0 (5)	C29—C28—C35—C36	133.4 (3)
C15—C16—C17—C18	0.1 (7)	C24—C28—C35—C36	8.3 (4)
C16—C17—C18—C19	0.5 (8)	O5—C28—C35—C40	63.6 (3)
C15—C14—C19—C18	−0.9 (7)	C29—C28—C35—C40	−52.6 (4)
C13—C14—C19—C18	−177.4 (5)	C24—C28—C35—C40	−177.7 (3)
C17—C18—C19—C14	−0.1 (9)	C40—C35—C36—C37	−2.4 (4)
C21—O3—C20—O2	2.9 (4)	C28—C35—C36—C37	171.6 (3)
C21—O3—C20—C4	180.0 (3)	C35—C36—C37—C38	0.8 (5)
N3—C4—C20—O2	−5.5 (4)	C36—C37—C38—C39	0.9 (6)
C5—C4—C20—O2	−122.3 (3)	C37—C38—C39—C40	−1.1 (6)
N3—C4—C20—O3	177.4 (2)	C38—C39—C40—C35	−0.5 (6)
C5—C4—C20—O3	60.5 (3)	C36—C35—C40—C39	2.3 (5)
N1—C5—C22—O4	−46.7 (3)	C28—C35—C40—C39	−172.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5X···O4	0.83 (2)	2.00 (2)	2.762 (3)	153 (3)
C4—H4···O1ⁱ	0.98	2.57	3.328 (3)	135
C5—H5···O1ⁱ	0.98	2.57	3.320 (3)	133
C16—H16···O4ⁱ	0.93	2.62	3.383 (4)	139
C17—H17···O5ⁱ	0.93	2.80	3.544 (5)	138
C32—H32···O5ⁱⁱ	0.93	2.58	3.435 (5)	153
C37—H37···O1ⁱⁱⁱ	0.93	2.50	3.336 (4)	150

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

Experimental details

Crystal data
Chemical formula	C₃₇H₃₇N₃O₅
M_r	603.70
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	12.075 (4), 10.907 (4), 12.328 (4)
β (°)	101.396 (5)
V (Å³)	1591.5 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	8080, 3679, 2645
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.02
No. of reflections	3679
No. of parameters	411
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)	0.13, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5X···O4	0.825 (18)	2.00 (2)	2.762 (3)	153 (3)
C4—H4···O1ⁱ	0.98	2.57	3.328 (3)	134.5
C5—H5···O1ⁱ	0.98	2.57	3.320 (3)	133.0
C16—H16···O4ⁱ	0.93	2.62	3.383 (4)	139.4
C17—H17···O5ⁱ	0.93	2.80	3.544 (5)	138.2
C32—H32···O5ⁱⁱ	0.93	2.58	3.435 (5)	152.7
C37—H37···O1ⁱⁱⁱ	0.93	2.50	3.336 (4)	150.3

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

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