Crystal structure of 4-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yl] 2-methyl (2S,4S,5R)-1-[(2S,3R,5R)-5-meth­oxy­carbonyl-2-(2-methyl­phen­yl)pyrrolidine-3-carbon­yl]-5-(2-methyl­phen­yl)pyrrolidine-2,4-di­carboxyl­ate

The title compound represents a chiral β-proline dipeptide. Corresponding stereogenic centres of constituting pyrrolidine units have opposite absolute configurations. The central amide fragment is planar within 0.1 Å and adopts a Z configuration along the N—CO bond.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.060
• wR factor = 0.113
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.169
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00767 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H49A     ..O7       .       2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.646 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.169 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT791_ALERT_4_G Model has Chirality at C1          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C19         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C20         (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C22         (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C44         (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C45         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C48         (Chiral SPGR)          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl] 2-methyl (2S,4S,5R)-1-[(2S,3R,5R)-5-methoxycarbonyl-2-(2-methylphenyl)pyrrolidine-3-carbonyl]-5-(2-methylphenyl)pyrrolidine-2,4-dicarboxylate

Crystal data

C38H50N2O7	F(000) = 1392
Mr = 646.80	Dx = 1.244 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2257 reflections
a = 10.993 (8) Å	θ = 2.4–20.4°
b = 13.198 (10) Å	µ = 0.09 mm^−1
c = 23.799 (19) Å	T = 150 K
V = 3453 (5) Å^3	Needle, colourless
Z = 4	0.50 × 0.10 × 0.04 mm

Data collection

Bruker SMART APEXII diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	1990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.169
ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.959, Tmax = 0.997	k = −15→15
19713 measured reflections	l = −27→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0294P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3438 reflections	Δρmax = 0.19 e Å^−3
436 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.3110 (4)	0.8167 (3)	0.43708 (16)	0.0312 (10)
N2	0.4319 (4)	1.1224 (3)	0.4206 (2)	0.0436 (12)
H11	0.407 (6)	1.116 (5)	0.457 (3)	0.10 (3)*
O1	0.1121 (3)	0.5592 (3)	0.37321 (14)	0.0422 (9)
O2	0.0621 (4)	0.6760 (3)	0.30922 (16)	0.0501 (11)
O3	0.2308 (3)	0.7761 (3)	0.58012 (14)	0.0464 (10)
O4	0.3899 (3)	0.7031 (3)	0.53704 (15)	0.0442 (9)
O5	0.4036 (3)	0.9273 (2)	0.49501 (14)	0.0403 (9)
O6	0.7399 (3)	1.1224 (3)	0.47147 (16)	0.0510 (10)
O7	0.5675 (3)	1.1762 (3)	0.51165 (17)	0.0573 (12)
C1	0.2786 (4)	0.7736 (4)	0.3819 (2)	0.0334 (12)
H1	0.2707	0.8293	0.3537	0.040*
C2	0.1512 (4)	0.7294 (4)	0.3953 (2)	0.0349 (13)
H2	0.0931	0.7877	0.3943	0.042*
C3	0.1600 (4)	0.6968 (4)	0.4560 (2)	0.0358 (13)
H3A	0.2042	0.6318	0.4596	0.043*
H3B	0.0784	0.6897	0.4731	0.043*
C4	0.2309 (4)	0.7833 (4)	0.48281 (19)	0.0341 (13)
H4	0.1733	0.8393	0.4923	0.041*
C5	0.3734 (4)	0.6966 (4)	0.3617 (2)	0.0325 (12)
C6	0.3970 (5)	0.6843 (4)	0.3047 (2)	0.0378 (13)
C7	0.4838 (5)	0.6134 (4)	0.2886 (2)	0.0454 (15)
H7	0.5010	0.6046	0.2498	0.054*
C8	0.5454 (5)	0.5555 (5)	0.3274 (2)	0.0482 (15)
H8	0.6047	0.5078	0.3154	0.058*
C9	0.5203 (5)	0.5676 (4)	0.3839 (2)	0.0469 (15)
H9	0.5608	0.5272	0.4111	0.056*
C10	0.4355 (4)	0.6392 (4)	0.4004 (2)	0.0393 (13)
H10	0.4199	0.6488	0.4393	0.047*
C11	0.1050 (5)	0.6535 (4)	0.3537 (2)	0.0347 (13)
C12	0.2549 (5)	0.4131 (4)	0.3088 (2)	0.0519 (16)
H12	0.2946	0.4681	0.3312	0.062*
C13	0.3418 (6)	0.3231 (5)	0.3088 (3)	0.074 (2)
H13A	0.3423	0.2917	0.3461	0.111*
H13B	0.4240	0.3464	0.2995	0.111*
H13C	0.3150	0.2734	0.2809	0.111*
C14	0.2384 (6)	0.4538 (5)	0.2488 (2)	0.0645 (18)
H14A	0.3182	0.4697	0.2327	0.097*
H14B	0.1886	0.5154	0.2498	0.097*
H14C	0.1981	0.4024	0.2257	0.097*
C15	−0.2423 (5)	0.3419 (4)	0.3906 (3)	0.0611 (18)
H15A	−0.2895	0.2858	0.3748	0.092*
H15B	−0.2943	0.4019	0.3940	0.092*
H15C	−0.2118	0.3227	0.4278	0.092*
C16	0.2962 (5)	0.7515 (4)	0.5349 (2)	0.0357 (13)
C17	0.2759 (5)	0.7423 (5)	0.6340 (2)	0.0579 (17)
H17A	0.2106	0.7463	0.6619	0.087*
H17B	0.3437	0.7857	0.6457	0.087*
H17C	0.3041	0.6721	0.6310	0.087*
C18	0.3889 (5)	0.8945 (4)	0.4471 (2)	0.0334 (12)
C19	0.3782 (4)	1.0456 (4)	0.3845 (2)	0.0376 (13)
H19	0.3982	1.0647	0.3449	0.045*
C20	0.4485 (4)	0.9445 (4)	0.3976 (2)	0.0378 (13)
H20	0.4506	0.8986	0.3642	0.045*
C21	0.5763 (4)	0.9835 (4)	0.4127 (2)	0.0437 (15)
H21A	0.6346	0.9690	0.3820	0.052*
H21B	0.6060	0.9513	0.4476	0.052*
C22	0.5611 (5)	1.0986 (4)	0.4208 (2)	0.0412 (14)
H22	0.5995	1.1335	0.3880	0.049*
C23	0.6197 (5)	1.1381 (4)	0.4736 (3)	0.0430 (14)
C24	0.8099 (5)	1.1593 (5)	0.5196 (3)	0.0618 (18)
H24A	0.8920	1.1779	0.5073	0.093*
H24B	0.8152	1.1059	0.5481	0.093*
H24C	0.7695	1.2188	0.5356	0.093*
C25	0.2412 (4)	1.0401 (3)	0.3886 (2)	0.0349 (13)
C26	0.1694 (5)	1.0283 (4)	0.3403 (2)	0.0381 (13)
C27	0.0444 (5)	1.0164 (4)	0.3473 (3)	0.0551 (17)
H27	−0.0051	1.0071	0.3150	0.066*
C28	−0.0096 (6)	1.0178 (4)	0.3992 (4)	0.066 (2)
H28	−0.0951	1.0091	0.4025	0.080*
C29	0.0595 (6)	1.0314 (5)	0.4460 (3)	0.0619 (19)
H29	0.0223	1.0322	0.4821	0.074*
C30	0.1839 (5)	1.0443 (4)	0.4410 (2)	0.0478 (15)
H30	0.2313	1.0562	0.4738	0.057*
C31	0.2218 (5)	1.0293 (4)	0.2826 (2)	0.0540 (17)
H31A	0.1569	1.0182	0.2551	0.081*
H31B	0.2827	0.9754	0.2792	0.081*
H31C	0.2604	1.0951	0.2755	0.081*
C32	0.3347 (5)	0.7466 (4)	0.2601 (2)	0.0518 (16)
H32A	0.2468	0.7472	0.2671	0.078*
H32B	0.3509	0.7170	0.2231	0.078*
H32C	0.3659	0.8161	0.2612	0.078*
C44	0.0484 (5)	0.4778 (4)	0.3427 (2)	0.0407 (14)
H44A	0.0258	0.5020	0.3043	0.049*
C45	0.1339 (5)	0.3885 (4)	0.3380 (2)	0.0451 (14)
H45	0.1538	0.3664	0.3771	0.054*
C46	0.0616 (5)	0.3019 (4)	0.3104 (2)	0.0557 (17)
H46A	0.0371	0.3220	0.2720	0.067*
H46B	0.1137	0.2409	0.3075	0.067*
C47	−0.0515 (5)	0.2770 (4)	0.3450 (3)	0.0550 (16)
H47A	−0.0964	0.2213	0.3264	0.066*
H47B	−0.0260	0.2528	0.3825	0.066*
C48	−0.1351 (5)	0.3657 (4)	0.3520 (2)	0.0468 (15)
H48	−0.1676	0.3849	0.3142	0.056*
C49	−0.0645 (5)	0.4561 (4)	0.3758 (2)	0.0426 (14)
H49C	−0.1175	0.5168	0.3755	0.051*
H49A	−0.0421	0.4418	0.4153	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.032 (2)	0.026 (3)	0.035 (2)	−0.003 (2)	0.002 (2)	0.0005 (19)
N2	0.036 (3)	0.038 (3)	0.056 (3)	−0.003 (2)	−0.008 (3)	−0.002 (3)
O1	0.050 (2)	0.028 (2)	0.048 (2)	−0.0019 (18)	−0.012 (2)	−0.0016 (17)
O2	0.064 (3)	0.035 (2)	0.051 (2)	−0.006 (2)	−0.018 (2)	0.0069 (19)
O3	0.044 (2)	0.060 (3)	0.036 (2)	0.0077 (19)	0.006 (2)	0.0026 (18)
O4	0.042 (2)	0.040 (2)	0.050 (2)	0.0087 (19)	−0.005 (2)	0.0033 (17)
O5	0.047 (2)	0.033 (2)	0.041 (2)	−0.0036 (17)	0.002 (2)	−0.0061 (17)
O6	0.044 (2)	0.051 (3)	0.058 (3)	−0.0057 (19)	−0.005 (2)	−0.011 (2)
O7	0.045 (3)	0.068 (3)	0.059 (3)	−0.001 (2)	0.002 (2)	−0.018 (2)
C1	0.032 (3)	0.033 (3)	0.036 (3)	−0.006 (2)	0.001 (3)	−0.002 (2)
C2	0.031 (3)	0.035 (3)	0.039 (3)	0.004 (2)	−0.001 (3)	0.000 (3)
C3	0.029 (3)	0.036 (3)	0.043 (3)	−0.005 (2)	0.002 (3)	0.001 (3)
C4	0.026 (3)	0.036 (3)	0.040 (3)	0.002 (2)	0.001 (3)	−0.002 (2)
C5	0.031 (3)	0.030 (3)	0.036 (3)	−0.005 (2)	0.001 (3)	0.000 (2)
C6	0.034 (3)	0.041 (4)	0.039 (3)	−0.007 (3)	0.000 (3)	0.001 (3)
C7	0.040 (3)	0.054 (4)	0.042 (3)	0.004 (3)	0.009 (3)	−0.004 (3)
C8	0.037 (3)	0.053 (4)	0.055 (4)	0.009 (3)	0.001 (3)	−0.010 (3)
C9	0.039 (3)	0.047 (4)	0.055 (4)	0.007 (3)	−0.003 (3)	−0.001 (3)
C10	0.028 (3)	0.044 (4)	0.045 (3)	0.002 (3)	−0.004 (3)	−0.006 (3)
C11	0.024 (3)	0.031 (4)	0.049 (3)	0.003 (2)	0.003 (3)	0.006 (3)
C12	0.055 (4)	0.049 (4)	0.052 (4)	0.004 (3)	0.005 (3)	−0.014 (3)
C13	0.069 (5)	0.056 (5)	0.097 (5)	0.013 (4)	0.018 (4)	−0.013 (4)
C14	0.063 (4)	0.079 (5)	0.052 (4)	−0.006 (4)	0.009 (4)	−0.013 (3)
C15	0.062 (4)	0.045 (4)	0.076 (4)	−0.012 (3)	−0.008 (4)	0.008 (3)
C16	0.033 (3)	0.034 (3)	0.041 (3)	−0.004 (3)	0.003 (3)	0.006 (3)
C17	0.061 (4)	0.079 (5)	0.034 (3)	0.007 (3)	0.000 (3)	0.005 (3)
C18	0.031 (3)	0.029 (3)	0.040 (3)	0.004 (3)	0.001 (3)	−0.001 (3)
C19	0.038 (3)	0.036 (4)	0.039 (3)	0.001 (3)	−0.001 (3)	0.002 (3)
C20	0.034 (3)	0.033 (3)	0.047 (3)	−0.002 (2)	0.009 (3)	−0.010 (3)
C21	0.035 (3)	0.040 (4)	0.056 (4)	−0.010 (2)	0.006 (3)	−0.008 (3)
C22	0.045 (3)	0.031 (4)	0.047 (3)	−0.014 (3)	0.001 (3)	0.001 (3)
C23	0.036 (3)	0.036 (4)	0.057 (4)	−0.004 (3)	0.002 (3)	−0.002 (3)
C24	0.043 (4)	0.076 (5)	0.066 (4)	0.000 (3)	−0.007 (4)	−0.019 (3)
C25	0.035 (3)	0.022 (3)	0.048 (3)	0.002 (2)	0.004 (3)	0.003 (2)
C26	0.031 (3)	0.028 (3)	0.055 (4)	−0.001 (2)	−0.001 (3)	0.001 (3)
C27	0.040 (4)	0.042 (4)	0.084 (5)	0.001 (3)	−0.002 (4)	−0.002 (3)
C28	0.033 (4)	0.042 (4)	0.124 (7)	0.007 (3)	0.015 (5)	0.019 (4)
C29	0.048 (4)	0.055 (5)	0.083 (5)	0.021 (3)	0.018 (4)	0.019 (4)
C30	0.047 (4)	0.040 (4)	0.056 (4)	0.012 (3)	0.007 (3)	0.010 (3)
C31	0.050 (4)	0.052 (4)	0.060 (4)	0.005 (3)	−0.011 (3)	−0.016 (3)
C32	0.054 (4)	0.053 (4)	0.048 (3)	0.009 (3)	0.009 (3)	0.002 (3)
C44	0.049 (4)	0.028 (3)	0.044 (3)	−0.004 (3)	−0.011 (3)	−0.005 (3)
C45	0.044 (3)	0.040 (4)	0.051 (3)	0.003 (3)	−0.004 (3)	−0.007 (3)
C46	0.063 (4)	0.038 (4)	0.066 (4)	−0.002 (3)	0.000 (4)	−0.013 (3)
C47	0.066 (4)	0.034 (4)	0.065 (4)	−0.011 (3)	−0.015 (4)	−0.004 (3)
C48	0.044 (4)	0.038 (4)	0.058 (4)	−0.003 (3)	−0.010 (3)	0.010 (3)
C49	0.048 (3)	0.030 (3)	0.050 (3)	0.002 (3)	−0.006 (3)	0.005 (3)

Geometric parameters (Å, º)

N1—C18	1.357 (6)	C15—H15C	0.9800
N1—C4	1.468 (6)	C17—H17A	0.9800
N1—C1	1.475 (6)	C17—H17B	0.9800
N2—C19	1.453 (6)	C17—H17C	0.9800
N2—C22	1.455 (7)	C18—C20	1.501 (7)
N2—H11	0.91 (6)	C19—C25	1.511 (7)
O1—C11	1.331 (6)	C19—C20	1.573 (7)
O1—C44	1.473 (6)	C19—H19	1.0000
O2—C11	1.196 (6)	C20—C21	1.538 (7)
O3—C16	1.333 (6)	C20—H20	1.0000
O3—C17	1.446 (6)	C21—C22	1.540 (7)
O4—C16	1.213 (6)	C21—H21A	0.9900
O5—C18	1.231 (5)	C21—H21B	0.9900
O6—C23	1.339 (6)	C22—C23	1.505 (7)
O6—C24	1.464 (6)	C22—H22	1.0000
O7—C23	1.185 (6)	C24—H24A	0.9800
C1—C5	1.533 (7)	C24—H24B	0.9800
C1—C2	1.550 (6)	C24—H24C	0.9800
C1—H1	1.0000	C25—C30	1.399 (7)
C2—C11	1.497 (7)	C25—C26	1.403 (7)
C2—C3	1.511 (7)	C26—C27	1.393 (7)
C2—H2	1.0000	C26—C31	1.489 (8)
C3—C4	1.523 (7)	C27—C28	1.370 (9)
C3—H3A	0.9900	C27—H27	0.9500
C3—H3B	0.9900	C28—C29	1.360 (9)
C4—C16	1.493 (7)	C28—H28	0.9500
C4—H4	1.0000	C29—C30	1.384 (8)
C5—C10	1.376 (7)	C29—H29	0.9500
C5—C6	1.389 (6)	C30—H30	0.9500
C6—C7	1.391 (7)	C31—H31A	0.9800
C6—C32	1.507 (7)	C31—H31B	0.9800
C7—C8	1.376 (7)	C31—H31C	0.9800
C7—H7	0.9500	C32—H32A	0.9800
C8—C9	1.382 (7)	C32—H32B	0.9800
C8—H8	0.9500	C32—H32C	0.9800
C9—C10	1.384 (7)	C44—C49	1.498 (7)
C9—H9	0.9500	C44—C45	1.512 (7)
C10—H10	0.9500	C44—H44A	1.0000
C12—C13	1.524 (8)	C45—C46	1.539 (7)
C12—C45	1.536 (7)	C45—H45	1.0000
C12—C14	1.537 (7)	C46—C47	1.525 (7)
C12—H12	1.0000	C46—H46A	0.9900
C13—H13A	0.9800	C46—H46B	0.9900
C13—H13B	0.9800	C47—C48	1.498 (8)
C13—H13C	0.9800	C47—H47A	0.9900
C14—H14A	0.9800	C47—H47B	0.9900
C14—H14B	0.9800	C48—C49	1.532 (7)
C14—H14C	0.9800	C48—H48	1.0000
C15—C48	1.527 (7)	C49—H49C	0.9900
C15—H15A	0.9800	C49—H49A	0.9900
C15—H15B	0.9800
C18—N1—C4	118.4 (4)	C20—C19—H19	107.0
C18—N1—C1	126.9 (4)	C18—C20—C21	111.3 (5)
C4—N1—C1	113.5 (4)	C18—C20—C19	108.3 (4)
C19—N2—C22	104.4 (4)	C21—C20—C19	102.2 (4)
C19—N2—H11	112 (4)	C18—C20—H20	111.6
C22—N2—H11	106 (4)	C21—C20—H20	111.6
C11—O1—C44	118.8 (4)	C19—C20—H20	111.6
C16—O3—C17	117.1 (4)	C20—C21—C22	105.1 (4)
C23—O6—C24	116.0 (5)	C20—C21—H21A	110.7
N1—C1—C5	111.8 (4)	C22—C21—H21A	110.7
N1—C1—C2	100.4 (4)	C20—C21—H21B	110.7
C5—C1—C2	115.4 (4)	C22—C21—H21B	110.7
N1—C1—H1	109.6	H21A—C21—H21B	108.8
C5—C1—H1	109.6	N2—C22—C23	110.2 (5)
C2—C1—H1	109.6	N2—C22—C21	108.5 (4)
C11—C2—C3	117.6 (4)	C23—C22—C21	113.6 (5)
C11—C2—C1	115.0 (4)	N2—C22—H22	108.1
C3—C2—C1	104.2 (4)	C23—C22—H22	108.1
C11—C2—H2	106.4	C21—C22—H22	108.1
C3—C2—H2	106.4	O7—C23—O6	124.9 (5)
C1—C2—H2	106.4	O7—C23—C22	125.3 (5)
C2—C3—C4	102.7 (4)	O6—C23—C22	109.7 (5)
C2—C3—H3A	111.2	O6—C24—H24A	109.5
C4—C3—H3A	111.2	O6—C24—H24B	109.5
C2—C3—H3B	111.2	H24A—C24—H24B	109.5
C4—C3—H3B	111.2	O6—C24—H24C	109.5
H3A—C3—H3B	109.1	H24A—C24—H24C	109.5
N1—C4—C16	114.4 (4)	H24B—C24—H24C	109.5
N1—C4—C3	102.8 (4)	C30—C25—C26	118.8 (5)
C16—C4—C3	112.6 (4)	C30—C25—C19	120.3 (5)
N1—C4—H4	109.0	C26—C25—C19	120.9 (5)
C16—C4—H4	109.0	C27—C26—C25	118.0 (6)
C3—C4—H4	109.0	C27—C26—C31	119.6 (6)
C10—C5—C6	119.8 (5)	C25—C26—C31	122.5 (5)
C10—C5—C1	119.4 (4)	C28—C27—C26	122.3 (6)
C6—C5—C1	120.7 (5)	C28—C27—H27	118.9
C5—C6—C7	118.4 (5)	C26—C27—H27	118.9
C5—C6—C32	122.6 (5)	C29—C28—C27	119.9 (6)
C7—C6—C32	119.0 (5)	C29—C28—H28	120.0
C8—C7—C6	121.8 (5)	C27—C28—H28	120.0
C8—C7—H7	119.1	C28—C29—C30	119.8 (7)
C6—C7—H7	119.1	C28—C29—H29	120.1
C7—C8—C9	119.4 (5)	C30—C29—H29	120.1
C7—C8—H8	120.3	C29—C30—C25	121.1 (6)
C9—C8—H8	120.3	C29—C30—H30	119.4
C8—C9—C10	119.3 (5)	C25—C30—H30	119.4
C8—C9—H9	120.3	C26—C31—H31A	109.5
C10—C9—H9	120.3	C26—C31—H31B	109.5
C5—C10—C9	121.3 (5)	H31A—C31—H31B	109.5
C5—C10—H10	119.4	C26—C31—H31C	109.5
C9—C10—H10	119.4	H31A—C31—H31C	109.5
O2—C11—O1	124.3 (5)	H31B—C31—H31C	109.5
O2—C11—C2	123.6 (5)	C6—C32—H32A	109.5
O1—C11—C2	112.0 (5)	C6—C32—H32B	109.5
C13—C12—C45	112.2 (5)	H32A—C32—H32B	109.5
C13—C12—C14	110.3 (5)	C6—C32—H32C	109.5
C45—C12—C14	113.1 (5)	H32A—C32—H32C	109.5
C13—C12—H12	107.0	H32B—C32—H32C	109.5
C45—C12—H12	107.0	O1—C44—C49	105.9 (4)
C14—C12—H12	107.0	O1—C44—C45	108.1 (4)
C12—C13—H13A	109.5	C49—C44—C45	113.9 (4)
C12—C13—H13B	109.5	O1—C44—H44A	109.6
H13A—C13—H13B	109.5	C49—C44—H44A	109.6
C12—C13—H13C	109.5	C45—C44—H44A	109.6
H13A—C13—H13C	109.5	C44—C45—C12	114.0 (5)
H13B—C13—H13C	109.5	C44—C45—C46	106.9 (4)
C12—C14—H14A	109.5	C12—C45—C46	114.3 (5)
C12—C14—H14B	109.5	C44—C45—H45	107.1
H14A—C14—H14B	109.5	C12—C45—H45	107.1
C12—C14—H14C	109.5	C46—C45—H45	107.1
H14A—C14—H14C	109.5	C47—C46—C45	110.5 (5)
H14B—C14—H14C	109.5	C47—C46—H46A	109.5
C48—C15—H15A	109.5	C45—C46—H46A	109.5
C48—C15—H15B	109.5	C47—C46—H46B	109.5
H15A—C15—H15B	109.5	C45—C46—H46B	109.5
C48—C15—H15C	109.5	H46A—C46—H46B	108.1
H15A—C15—H15C	109.5	C48—C47—C46	113.1 (5)
H15B—C15—H15C	109.5	C48—C47—H47A	109.0
O4—C16—O3	123.5 (5)	C46—C47—H47A	109.0
O4—C16—C4	126.2 (5)	C48—C47—H47B	109.0
O3—C16—C4	110.1 (4)	C46—C47—H47B	109.0
O3—C17—H17A	109.5	H47A—C47—H47B	107.8
O3—C17—H17B	109.5	C47—C48—C15	112.3 (5)
H17A—C17—H17B	109.5	C47—C48—C49	109.8 (4)
O3—C17—H17C	109.5	C15—C48—C49	109.2 (5)
H17A—C17—H17C	109.5	C47—C48—H48	108.5
H17B—C17—H17C	109.5	C15—C48—H48	108.5
O5—C18—N1	120.7 (5)	C49—C48—H48	108.5
O5—C18—C20	121.0 (5)	C44—C49—C48	112.0 (4)
N1—C18—C20	118.1 (4)	C44—C49—H49C	109.2
N2—C19—C25	113.6 (4)	C48—C49—H49C	109.2
N2—C19—C20	106.0 (4)	C44—C49—H49A	109.2
C25—C19—C20	115.9 (4)	C48—C49—H49A	109.2
N2—C19—H19	107.0	H49C—C49—H49A	107.9
C25—C19—H19	107.0
C18—N1—C1—C5	82.6 (6)	N1—C18—C20—C19	100.2 (5)
C4—N1—C1—C5	−110.1 (4)	N2—C19—C20—C18	85.9 (5)
C18—N1—C1—C2	−154.5 (4)	C25—C19—C20—C18	−41.1 (6)
C4—N1—C1—C2	12.8 (5)	N2—C19—C20—C21	−31.7 (5)
N1—C1—C2—C11	−163.0 (4)	C25—C19—C20—C21	−158.6 (5)
C5—C1—C2—C11	−42.6 (6)	C18—C20—C21—C22	−102.5 (5)
N1—C1—C2—C3	−32.9 (5)	C19—C20—C21—C22	12.9 (5)
C5—C1—C2—C3	87.5 (5)	C19—N2—C22—C23	−154.8 (4)
C11—C2—C3—C4	169.7 (4)	C19—N2—C22—C21	−29.9 (6)
C1—C2—C3—C4	41.1 (5)	C20—C21—C22—N2	9.5 (6)
C18—N1—C4—C16	−57.3 (6)	C20—C21—C22—C23	132.5 (5)
C1—N1—C4—C16	134.2 (4)	C24—O6—C23—O7	−2.5 (8)
C18—N1—C4—C3	−179.7 (4)	C24—O6—C23—C22	178.5 (4)
C1—N1—C4—C3	11.9 (5)	N2—C22—C23—O7	5.4 (8)
C2—C3—C4—N1	−32.2 (5)	C21—C22—C23—O7	−116.6 (6)
C2—C3—C4—C16	−155.7 (4)	N2—C22—C23—O6	−175.6 (4)
N1—C1—C5—C10	31.8 (6)	C21—C22—C23—O6	62.4 (6)
C2—C1—C5—C10	−82.1 (6)	N2—C19—C25—C30	−43.5 (6)
N1—C1—C5—C6	−148.2 (4)	C20—C19—C25—C30	79.5 (6)
C2—C1—C5—C6	97.8 (6)	N2—C19—C25—C26	138.0 (5)
C10—C5—C6—C7	0.0 (8)	C20—C19—C25—C26	−99.0 (6)
C1—C5—C6—C7	−179.9 (5)	C30—C25—C26—C27	−3.1 (7)
C10—C5—C6—C32	−178.4 (5)	C19—C25—C26—C27	175.4 (5)
C1—C5—C6—C32	1.7 (8)	C30—C25—C26—C31	176.2 (5)
C5—C6—C7—C8	0.4 (8)	C19—C25—C26—C31	−5.3 (7)
C32—C6—C7—C8	178.8 (5)	C25—C26—C27—C28	1.2 (8)
C6—C7—C8—C9	0.3 (9)	C31—C26—C27—C28	−178.1 (5)
C7—C8—C9—C10	−1.4 (9)	C26—C27—C28—C29	0.3 (9)
C6—C5—C10—C9	−1.1 (8)	C27—C28—C29—C30	0.2 (9)
C1—C5—C10—C9	178.9 (4)	C28—C29—C30—C25	−2.2 (9)
C8—C9—C10—C5	1.8 (8)	C26—C25—C30—C29	3.6 (7)
C44—O1—C11—O2	−9.1 (7)	C19—C25—C30—C29	−174.9 (5)
C44—O1—C11—C2	167.9 (4)	C11—O1—C44—C49	−102.4 (5)
C3—C2—C11—O2	158.3 (5)	C11—O1—C44—C45	135.1 (5)
C1—C2—C11—O2	−78.4 (6)	O1—C44—C45—C12	−57.3 (6)
C3—C2—C11—O1	−18.7 (6)	C49—C44—C45—C12	−174.7 (4)
C1—C2—C11—O1	104.6 (5)	O1—C44—C45—C46	175.4 (4)
C17—O3—C16—O4	−0.1 (7)	C49—C44—C45—C46	58.0 (6)
C17—O3—C16—C4	174.5 (4)	C13—C12—C45—C44	175.8 (5)
N1—C4—C16—O4	−39.9 (7)	C14—C12—C45—C44	−58.7 (6)
C3—C4—C16—O4	76.9 (6)	C13—C12—C45—C46	−60.9 (6)
N1—C4—C16—O3	145.6 (4)	C14—C12—C45—C46	64.6 (6)
C3—C4—C16—O3	−97.5 (5)	C44—C45—C46—C47	−57.6 (6)
C4—N1—C18—O5	9.4 (7)	C12—C45—C46—C47	175.3 (5)
C1—N1—C18—O5	176.1 (5)	C45—C46—C47—C48	58.6 (6)
C4—N1—C18—C20	−165.7 (4)	C46—C47—C48—C15	−175.3 (4)
C1—N1—C18—C20	1.0 (7)	C46—C47—C48—C49	−53.6 (6)
C22—N2—C19—C25	166.6 (4)	O1—C44—C49—C48	−174.8 (4)
C22—N2—C19—C20	38.2 (5)	C45—C44—C49—C48	−56.2 (6)
O5—C18—C20—C21	36.7 (7)	C47—C48—C49—C44	51.4 (6)
N1—C18—C20—C21	−148.3 (4)	C15—C48—C49—C44	174.9 (4)
O5—C18—C20—C19	−74.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O4^i	0.99	2.52	3.254 (6)	131
C3—H3B···O5^i	0.99	2.58	3.462 (6)	149
C49—H49A···O7^i	0.99	2.63	3.511 (7)	149

Symmetry code: (i) x−1/2, −y+3/2, −z+1.