2,4,6-Tris{[(S)-1-hydr­oxy-3-methyl­butan-2-ylamino]methyl­ene}cyclo­hexane-1,3,5-trione

Suresh, P.; Varghese, B.; Varadarajan, T.K.; Viswanathan, B.

doi:10.1107/S1600536807001754

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2,4,6-Tris{[(S)-1-hydroxy-3-methylbutan-2-ylamino]methylene}cyclohexane-1,3,5-trione

P. Suresh, B. Varghese, T. K. Varadarajan and B. Viswanathan

The title compound, C₂₄H₃₉N₃O₆, also known as tris[(S)-N-salicylidenevalinol], crystallizes with two molecules in the asymmetric unit. These two molecules form a disc-shaped dimeric box and are linked to each other through 11 O—H

O hydrogen bonds. These self-assembled dimers are connected by a 12th hydrogen bond to form a one-dimensional hydrogen-bonded network along the b-axis direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001754/om2086sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001754/om2086Isup2.hkl Contains datablock I

CCDC reference: 286211

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
Disorder in main residue
R factor = 0.066
wR factor = 0.202
Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       2.33 Sigma
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.97 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.16 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C40
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C46
PLAT415_ALERT_2_B Short Inter D-H..H-X       H4     ..  H31     ..       2.02 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.84
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.84 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C39
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C38
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT245_ALERT_2_C U(iso) H3N     Smaller than U(eq) N3      by ...       0.02 AngSq
PLAT301_ALERT_3_C Main Residue  Disorder .........................       1.00 Perc.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C25    -C30           1.44 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C1     -C6            1.45 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT415_ALERT_2_C Short Inter D-H..H-X       H6     ..  H37     ..       2.12 Ang.
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure        !
PLAT731_ALERT_1_C Bond    Calc     0.83(4), Rep   0.834(10) ......       4.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.83(3), Rep   0.827(11) ......       2.73 su-Ra
              N2   -H2N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(4), Rep   0.823(10) ......       4.00 su-Ra
              N3   -H3N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.83(3), Rep   0.831(10) ......       3.00 su-Ra
              N5   -H5N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.83(4), Rep   0.830(10) ......       4.00 su-Ra
              N6   -H6N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(4), Rep   0.834(10) ......       4.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(3), Rep   0.827(11) ......       2.73 su-Ra
              N2   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(4), Rep   0.823(10) ......       4.00 su-Ra
              N3   -H3N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(3), Rep   0.831(10) ......       3.00 su-Ra
              N5   -H5N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(4), Rep   0.830(10) ......       4.00 su-Ra
              N6   -H6N     1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.90 Deg.
              O11' -C39  -O11     1.555   1.555   1.555

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      0.837
            Tmax scaled      0.835 Tmin scaled      0.807
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           67.96
           From the CIF: _reflns_number_total               5791
           Count of symmetry unique reflns         5792
           Completeness (_total/calc)             99.98%
           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 C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C44    = .          S

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

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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2,4,6-Tris{[(S)-1-hydroxy-3-methylbutan-2-ylamino]methylene}cyclohexane- 1,3,5-trione top

Crystal data top

C₂₄H₃₉N₃O₆	F(000) = 1008
M_r = 465.58	D_x = 1.026 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54180 Å
a = 16.7989 (12) Å	Cell parameters from 25 reflections
b = 11.2993 (14) Å	θ = 20–30°
c = 16.9258 (12) Å	µ = 0.60 mm⁻¹
β = 110.190 (5)°	T = 293 K
V = 3015.4 (5) Å³	Rectangular block, dark yellow
Z = 4	0.4 × 0.3 × 0.3 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	3817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 68.0°, θ_min = 2.8°
ω–2θ scans	h = 0→20
Absorption correction: ψ scan (North et al., 1968)	k = −13→0
T_min = 0.964, T_max = 0.998	l = −20→19
5998 measured reflections	2 standard reflections every 1 hour min
5791 independent reflections	intensity decay: none

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.202	w = 1/[σ²(F_o²) + (0.1452P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5791 reflections	Δρ_max = 0.42 e Å⁻³
621 parameters	Δρ_min = −0.28 e Å⁻³
24 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00035 (15)

Special details top

Experimental. [A]_D²⁵ = -274.8(c 0.35, CHCl₃); IR (KBr): 3322, 3054, 2965, 1613, 1546, 1458, 1377, 1307, 1265, 1074, 858, 841, 738, cm^-1; ¹H NMR (CDCl₃): δ 1.04–1.06 (d, J= 4.9 Hz, 6H), 1.93–1.95 (m, 1H), 3.26 (m, 1H), 3.60–3.66 (t, J= 12 Hz 1H), 3.94–3.97 (d, J= 12 Hz 1H), 6.43 (br, 1H) 8.01–8.04 (d, J= 12 Hz 1H), 11.57–11.63 (dd, J= 12 Hz, J= 12 Hz 1H); ¹³C NMR (CDCl₃): δ 17.95, 19.39, 29.34, 64.42, 70.46, 104.18, 158.53, 184.57; HRMS (ESI) calculated for C₂₄H₃₉N₃O₆ [M+H]⁺: calculated: 466.2917; observed: 466.2940.

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	Occ. (<1)
C1	0.8566 (3)	0.1964 (5)	0.2800 (3)	0.0504 (9)
C2	0.8297 (2)	0.1532 (5)	0.1932 (2)	0.0504 (9)
C3	0.7476 (2)	0.1805 (5)	0.1328 (3)	0.0507 (9)
C4	0.6904 (3)	0.2531 (5)	0.1612 (3)	0.0549 (10)
C5	0.7165 (3)	0.2998 (6)	0.2450 (3)	0.0583 (10)
C6	0.7998 (3)	0.2707 (6)	0.3040 (3)	0.0553 (10)
C7	0.8872 (3)	0.0845 (6)	0.1705 (3)	0.0548 (10)
H7	0.9392	0.0702	0.2124	0.066*
C8	0.9415 (3)	−0.0249 (6)	0.0748 (3)	0.0582 (10)
H8	0.9844	−0.0516	0.1274	0.070*
C9	0.9848 (3)	0.0603 (6)	0.0333 (3)	0.0713 (13)
H9A	1.0264	0.0174	0.0164	0.086*
H9B	0.9430	0.0926	−0.0171	0.086*
C10	0.9073 (3)	−0.1340 (6)	0.0216 (3)	0.0751 (14)
H10	0.9554	−0.1725	0.0119	0.090*
C11	0.8715 (6)	−0.2216 (7)	0.0671 (5)	0.111 (2)
H11A	0.8503	−0.2892	0.0318	0.134*
H11B	0.8260	−0.1854	0.0805	0.134*
H11C	0.9151	−0.2461	0.1180	0.134*
C12	0.8421 (4)	−0.1061 (8)	−0.0644 (4)	0.0950 (19)
H12A	0.8231	−0.1784	−0.0949	0.114*
H12B	0.8674	−0.0564	−0.0952	0.114*
H12C	0.7947	−0.0659	−0.0573	0.114*
C13	0.6104 (3)	0.2786 (6)	0.1026 (3)	0.0624 (11)
H13	0.5970	0.2473	0.0488	0.075*
C14	0.4715 (3)	0.3766 (7)	0.0579 (4)	0.0845 (17)
H14	0.4592	0.3243	0.0090	0.101*
C15	0.4781 (4)	0.5040 (8)	0.0282 (5)	0.101 (2)
H15A	0.4231	0.5286	−0.0104	0.121*
H15B	0.4936	0.5567	0.0763	0.121*
C16	0.4016 (4)	0.3638 (9)	0.0922 (5)	0.101 (2)
H16	0.3515	0.4018	0.0519	0.122*
C17	0.4181 (5)	0.4239 (10)	0.1762 (6)	0.122 (3)
H17A	0.3705	0.4117	0.1943	0.147*
H17B	0.4261	0.5072	0.1706	0.147*
H17C	0.4681	0.3909	0.2171	0.147*
C18	0.3800 (6)	0.2315 (10)	0.0951 (7)	0.143 (3)
H18A	0.3348	0.2233	0.1171	0.172*
H18B	0.4292	0.1900	0.1307	0.172*
H18C	0.3628	0.1990	0.0393	0.172*
C19	0.8243 (3)	0.3202 (6)	0.3838 (3)	0.0594 (11)
H19	0.7847	0.3681	0.3953	0.071*
C20	0.9222 (3)	0.3645 (6)	0.5265 (3)	0.0692 (12)
H20	0.8723	0.4035	0.5320	0.083*
C21	0.9868 (4)	0.4590 (7)	0.5310 (3)	0.0833 (16)
H21A	1.0110	0.4876	0.5884	0.100*
H21B	1.0323	0.4254	0.5152	0.100*
C22	0.9524 (4)	0.2713 (7)	0.5964 (3)	0.0810 (15)
H22	0.9989	0.2268	0.5879	0.097*
C23	0.8811 (5)	0.1841 (9)	0.5906 (5)	0.111 (2)
H23A	0.9011	0.1259	0.6344	0.133*
H23B	0.8633	0.1455	0.5368	0.133*
H23C	0.8340	0.2260	0.5971	0.133*
C24	0.9855 (5)	0.3255 (9)	0.6838 (4)	0.112 (2)
H24A	1.0044	0.2638	0.7250	0.134*
H24B	0.9410	0.3697	0.6936	0.134*
H24C	1.0320	0.3774	0.6880	0.134*
C25	0.8898 (3)	0.4025 (6)	0.1088 (3)	0.0558 (10)
C26	0.9401 (3)	0.4206 (6)	0.1952 (3)	0.0552 (10)
C27	0.9106 (3)	0.4902 (6)	0.2501 (3)	0.0588 (10)
C28	0.8282 (3)	0.5442 (6)	0.2172 (3)	0.0610 (11)
C29	0.7733 (3)	0.5255 (6)	0.1305 (3)	0.0612 (11)
C30	0.8053 (3)	0.4556 (6)	0.0766 (3)	0.0571 (10)
C31	1.0186 (3)	0.3623 (6)	0.2258 (3)	0.0595 (10)
H31	1.0355	0.3213	0.1866	0.071*
C32	1.1491 (3)	0.2899 (7)	0.3360 (3)	0.0770 (14)
H32	1.1584	0.2533	0.2874	0.092*
C33	1.1364 (4)	0.1915 (7)	0.3904 (4)	0.0846 (16)
H33A	1.0884	0.1432	0.3583	0.101*
H33B	1.1864	0.1415	0.4091	0.101*
C34	1.2243 (3)	0.3710 (8)	0.3781 (4)	0.0948 (19)
H34	1.2098	0.4164	0.4205	0.114*
C35	1.2345 (5)	0.4595 (10)	0.3161 (6)	0.130 (3)
H35A	1.2816	0.5105	0.3437	0.156*
H35B	1.1837	0.5059	0.2942	0.156*
H35C	1.2447	0.4187	0.2707	0.156*
C36	1.3018 (5)	0.2975 (13)	0.4257 (7)	0.167 (5)
H36A	1.3489	0.3490	0.4523	0.201*
H36B	1.3156	0.2461	0.3871	0.201*
H36C	1.2899	0.2509	0.4677	0.201*
C37	0.8004 (3)	0.6100 (6)	0.2727 (3)	0.0699 (13)
H37	0.8378	0.6199	0.3274	0.084*
C38	0.6929 (4)	0.7244 (7)	0.3099 (4)	0.0897 (17)
H38	0.7407	0.7335	0.3627	0.108*
C39	0.6274 (6)	0.6490 (4)	0.3293 (5)	0.130 (3)
H39A	0.5990	0.6955	0.3599	0.156*
H39B	0.5851	0.6220	0.2773	0.156*
C40	0.6652 (5)	0.8440 (8)	0.2788 (6)	0.122 (3)
H40	0.6408	0.8779	0.3186	0.146*
C41	0.5973 (7)	0.8467 (14)	0.1970 (7)	0.188 (5)
H41A	0.5528	0.7939	0.1977	0.225*
H41B	0.6192	0.8222	0.1541	0.225*
H41C	0.5753	0.9256	0.1853	0.225*
C42	0.7411 (8)	0.9227 (14)	0.2843 (9)	0.219 (6)
H42A	0.7221	1.0026	0.2701	0.262*
H42B	0.7673	0.8944	0.2457	0.262*
H42C	0.7814	0.9204	0.3405	0.262*
C43	0.7536 (3)	0.4385 (6)	−0.0046 (3)	0.0641 (11)
H43	0.7007	0.4748	−0.0209	0.077*
C44	0.7125 (4)	0.3505 (7)	−0.1464 (3)	0.0810 (15)
H44	0.6653	0.4066	−0.1587	0.097*
C45	0.6764 (4)	0.2278 (8)	−0.1494 (4)	0.100 (2)
H45A	0.6417	0.2092	−0.2069	0.120*
H45B	0.7226	0.1711	−0.1315	0.120*
C46	0.7557 (6)	0.3705 (10)	−0.2108 (4)	0.116 (3)
H46	0.7150	0.3480	−0.2658	0.139*
C47	0.7777 (8)	0.4997 (13)	−0.2164 (6)	0.173 (5)
H47A	0.8045	0.5087	−0.2578	0.208*
H47B	0.8157	0.5258	−0.1626	0.208*
H47C	0.7268	0.5463	−0.2323	0.208*
C48	0.8304 (9)	0.2878 (15)	−0.1921 (8)	0.194 (6)
H48A	0.8580	0.3001	−0.2326	0.233*
H48B	0.8110	0.2074	−0.1954	0.233*
H48C	0.8697	0.3032	−0.1366	0.233*
N1	0.8759 (2)	0.0380 (5)	0.0970 (2)	0.0580 (9)
N2	0.5537 (3)	0.3427 (6)	0.1181 (3)	0.0797 (12)
N3	0.8957 (3)	0.3070 (5)	0.4434 (2)	0.0653 (10)
N4	1.0705 (2)	0.3597 (6)	0.3041 (2)	0.0674 (10)
N5	0.7244 (3)	0.6593 (6)	0.2525 (3)	0.0839 (13)
N6	0.7706 (3)	0.3759 (6)	−0.0623 (3)	0.0720 (11)
O1	0.92826 (19)	0.1697 (5)	0.33084 (18)	0.0660 (8)
O2	0.72580 (18)	0.1435 (5)	0.05807 (18)	0.0640 (8)
O3	0.6666 (2)	0.3661 (5)	0.2669 (2)	0.0758 (10)
O4	1.0255 (2)	0.1541 (5)	0.0871 (3)	0.0849 (10)
H4	0.9908	0.1899	0.1022	0.102*
O5	0.5388 (3)	0.5144 (7)	−0.0125 (3)	0.130 (2)
H5	0.5856	0.4951	0.0202	0.156*
O6	0.9502 (3)	0.5547 (5)	0.4771 (2)	0.1006 (13)
H6	0.9295	0.5306	0.4285	0.121*
O7	0.9162 (2)	0.3404 (5)	0.06022 (19)	0.0657 (8)
O8	0.9570 (2)	0.5022 (5)	0.3268 (2)	0.0755 (10)
O9	0.7009 (2)	0.5697 (5)	0.1033 (2)	0.0820 (10)
O10	1.1212 (3)	0.2414 (6)	0.4622 (3)	0.1057 (14)
H10A	1.1140	0.1879	0.4918	0.127*
O11	0.6680 (7)	0.5509 (7)	0.3782 (5)	0.121 (4)*	0.70 (2)
H11	0.6782	0.5011	0.3477	0.145*	0.70 (2)
O11'	0.6164 (17)	0.5329 (7)	0.3542 (13)	0.118 (8)*	0.30 (2)
H11'	0.6461	0.4873	0.3389	0.142*	0.30 (2)
O12	0.6274 (3)	0.2173 (7)	−0.0978 (3)	0.1139 (17)
H12	0.6567	0.2325	−0.0491	0.137*
H1N	0.8271 (16)	0.043 (6)	0.062 (3)	0.087 (19)*
H2N	0.571 (3)	0.369 (5)	0.1668 (16)	0.079 (18)*
H3N	0.9366 (18)	0.271 (4)	0.439 (3)	0.043 (11)*
H4N	1.064 (4)	0.403 (4)	0.341 (3)	0.077 (17)*
H5N	0.687 (3)	0.649 (5)	0.2059 (17)	0.073 (17)*
H6N	0.8160 (19)	0.339 (4)	−0.050 (3)	0.063 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.049 (2)	0.050 (2)	0.051 (2)	−0.0015 (18)	0.0157 (17)	0.0028 (18)
C2	0.054 (2)	0.051 (2)	0.050 (2)	−0.0013 (19)	0.0216 (17)	0.0001 (18)
C3	0.047 (2)	0.050 (2)	0.055 (2)	−0.0026 (18)	0.0177 (17)	−0.0011 (19)
C4	0.052 (2)	0.057 (2)	0.058 (2)	−0.001 (2)	0.0218 (18)	−0.003 (2)
C5	0.056 (2)	0.060 (3)	0.061 (2)	0.002 (2)	0.023 (2)	−0.003 (2)
C6	0.057 (2)	0.060 (2)	0.051 (2)	0.002 (2)	0.0202 (18)	−0.0013 (19)
C7	0.046 (2)	0.066 (3)	0.051 (2)	0.0017 (19)	0.0149 (17)	0.002 (2)
C8	0.055 (2)	0.060 (3)	0.062 (2)	0.006 (2)	0.0221 (19)	0.003 (2)
C9	0.069 (3)	0.076 (3)	0.077 (3)	−0.002 (3)	0.035 (2)	−0.006 (3)
C10	0.082 (3)	0.069 (3)	0.081 (3)	0.001 (3)	0.036 (3)	−0.016 (3)
C11	0.158 (7)	0.070 (4)	0.108 (5)	−0.021 (4)	0.050 (5)	−0.010 (4)
C12	0.094 (4)	0.107 (5)	0.080 (3)	−0.016 (4)	0.025 (3)	−0.029 (4)
C13	0.053 (2)	0.067 (3)	0.066 (2)	0.002 (2)	0.018 (2)	−0.005 (2)
C14	0.050 (2)	0.103 (5)	0.089 (4)	0.010 (3)	0.008 (2)	−0.001 (3)
C15	0.071 (3)	0.111 (5)	0.119 (5)	0.024 (3)	0.030 (3)	0.029 (4)
C16	0.066 (3)	0.113 (5)	0.121 (5)	0.011 (4)	0.026 (3)	−0.005 (4)
C17	0.095 (4)	0.132 (7)	0.152 (7)	0.020 (5)	0.058 (5)	−0.007 (6)
C18	0.123 (6)	0.117 (7)	0.189 (9)	−0.019 (5)	0.054 (6)	−0.009 (7)
C19	0.061 (2)	0.064 (3)	0.053 (2)	0.006 (2)	0.020 (2)	−0.004 (2)
C20	0.080 (3)	0.071 (3)	0.054 (2)	0.006 (3)	0.020 (2)	−0.010 (2)
C21	0.110 (4)	0.078 (4)	0.059 (3)	−0.013 (3)	0.026 (3)	−0.015 (3)
C22	0.094 (4)	0.081 (4)	0.065 (3)	0.006 (3)	0.024 (3)	−0.002 (3)
C23	0.125 (5)	0.108 (5)	0.094 (4)	0.000 (5)	0.032 (4)	0.018 (4)
C24	0.151 (6)	0.117 (6)	0.060 (3)	−0.002 (5)	0.027 (4)	−0.003 (4)
C25	0.060 (2)	0.061 (3)	0.051 (2)	−0.004 (2)	0.0248 (19)	−0.001 (2)
C26	0.055 (2)	0.061 (3)	0.050 (2)	−0.007 (2)	0.0190 (18)	0.0049 (19)
C27	0.064 (2)	0.061 (3)	0.053 (2)	−0.005 (2)	0.022 (2)	−0.001 (2)
C28	0.069 (3)	0.056 (3)	0.062 (2)	−0.001 (2)	0.028 (2)	−0.001 (2)
C29	0.060 (3)	0.062 (3)	0.063 (3)	0.001 (2)	0.021 (2)	0.003 (2)
C30	0.061 (2)	0.058 (3)	0.052 (2)	−0.006 (2)	0.0196 (19)	0.0012 (19)
C31	0.063 (2)	0.061 (3)	0.054 (2)	−0.004 (2)	0.0195 (19)	0.002 (2)
C32	0.070 (3)	0.089 (4)	0.067 (3)	0.007 (3)	0.017 (2)	−0.003 (3)
C33	0.083 (3)	0.083 (4)	0.077 (3)	0.006 (3)	0.013 (3)	0.005 (3)
C34	0.067 (3)	0.117 (5)	0.094 (4)	−0.004 (3)	0.020 (3)	0.005 (4)
C35	0.099 (5)	0.153 (8)	0.143 (7)	−0.037 (5)	0.046 (5)	0.013 (6)
C36	0.074 (4)	0.181 (11)	0.208 (10)	−0.004 (6)	0.001 (5)	0.006 (9)
C37	0.077 (3)	0.069 (3)	0.070 (3)	0.000 (3)	0.034 (2)	−0.009 (2)
C38	0.096 (4)	0.091 (4)	0.092 (4)	0.015 (3)	0.046 (3)	−0.017 (3)
C39	0.141 (6)	0.133 (8)	0.141 (7)	0.017 (6)	0.081 (6)	−0.021 (6)
C40	0.150 (7)	0.091 (5)	0.150 (7)	0.032 (5)	0.083 (6)	0.023 (5)
C41	0.213 (8)	0.181 (8)	0.162 (7)	0.048 (8)	0.054 (7)	0.023 (7)
C42	0.241 (10)	0.204 (10)	0.241 (10)	−0.010 (8)	0.121 (8)	−0.005 (8)
C43	0.066 (3)	0.065 (3)	0.062 (3)	−0.002 (2)	0.023 (2)	0.001 (2)
C44	0.084 (3)	0.095 (4)	0.054 (2)	−0.017 (3)	0.011 (2)	−0.004 (3)
C45	0.103 (4)	0.117 (5)	0.069 (3)	−0.034 (4)	0.017 (3)	−0.008 (3)
C46	0.134 (6)	0.154 (8)	0.062 (3)	−0.047 (6)	0.036 (4)	−0.014 (4)
C47	0.194 (10)	0.195 (12)	0.114 (6)	−0.088 (9)	0.031 (6)	0.038 (7)
C48	0.240 (13)	0.224 (15)	0.189 (11)	−0.059 (13)	0.163 (11)	−0.058 (11)
N1	0.054 (2)	0.068 (2)	0.0530 (19)	0.0026 (19)	0.0196 (17)	−0.0045 (18)
N2	0.061 (2)	0.097 (3)	0.075 (3)	0.017 (2)	0.016 (2)	−0.009 (3)
N3	0.072 (3)	0.067 (3)	0.055 (2)	0.010 (2)	0.0205 (19)	−0.0089 (18)
N4	0.062 (2)	0.081 (3)	0.056 (2)	0.005 (2)	0.0164 (18)	−0.004 (2)
N5	0.080 (3)	0.097 (4)	0.076 (3)	0.017 (3)	0.030 (2)	−0.013 (3)
N6	0.072 (3)	0.082 (3)	0.061 (2)	−0.005 (2)	0.021 (2)	−0.004 (2)
O1	0.0614 (17)	0.078 (2)	0.0512 (15)	0.0138 (16)	0.0107 (14)	−0.0022 (16)
O2	0.0583 (16)	0.077 (2)	0.0543 (16)	0.0016 (16)	0.0159 (13)	−0.0098 (16)
O3	0.0643 (18)	0.091 (3)	0.072 (2)	0.0178 (19)	0.0235 (16)	−0.0121 (19)
O4	0.075 (2)	0.073 (2)	0.112 (3)	−0.006 (2)	0.039 (2)	−0.007 (2)
O5	0.097 (3)	0.164 (6)	0.118 (4)	−0.003 (4)	0.022 (3)	0.023 (4)
O6	0.166 (4)	0.073 (2)	0.077 (2)	0.001 (3)	0.060 (3)	−0.007 (2)
O7	0.0719 (19)	0.074 (2)	0.0547 (16)	−0.0006 (17)	0.0258 (15)	−0.0042 (16)
O8	0.076 (2)	0.093 (3)	0.0534 (17)	0.0049 (19)	0.0159 (15)	−0.0158 (18)
O9	0.072 (2)	0.091 (3)	0.081 (2)	0.017 (2)	0.0250 (18)	−0.004 (2)
O10	0.132 (4)	0.101 (3)	0.080 (2)	−0.008 (3)	0.032 (2)	0.011 (2)
O12	0.096 (3)	0.153 (5)	0.088 (3)	−0.026 (3)	0.024 (2)	0.024 (3)

Geometric parameters (Å, º) top

C1—O1	1.251 (5)	C28—C37	1.398 (7)
C1—C6	1.432 (6)	C28—C29	1.455 (7)
C1—C2	1.464 (6)	C29—O9	1.247 (6)
C2—C7	1.393 (6)	C29—C30	1.444 (7)
C2—C3	1.438 (6)	C30—C43	1.363 (6)
C3—O2	1.261 (5)	C31—N4	1.311 (6)
C3—C4	1.465 (6)	C31—H31	0.9300
C4—C13	1.398 (6)	C32—N4	1.471 (7)
C4—C5	1.432 (6)	C32—C33	1.505 (9)
C5—O3	1.273 (6)	C32—C34	1.524 (9)
C5—C6	1.448 (6)	C32—H32	0.9800
C6—C19	1.386 (6)	C33—O10	1.440 (8)
C7—N1	1.304 (6)	C33—H33A	0.9700
C7—H7	0.9300	C33—H33B	0.9700
C8—N1	1.466 (6)	C34—C35	1.502 (11)
C8—C10	1.518 (7)	C34—C36	1.520 (12)
C8—C9	1.518 (7)	C34—H34	0.9800
C8—H8	0.9800	C35—H35A	0.9600
C9—O4	1.411 (7)	C35—H35B	0.9600
C9—H9A	0.9700	C35—H35C	0.9600
C9—H9B	0.9700	C36—H36A	0.9600
C10—C11	1.501 (9)	C36—H36B	0.9600
C10—C12	1.523 (8)	C36—H36C	0.9600
C10—H10	0.9800	C37—N5	1.325 (7)
C11—H11A	0.9600	C37—H37	0.9300
C11—H11B	0.9600	C38—N5	1.455 (7)
C11—H11C	0.9600	C38—C40	1.466 (11)
C12—H12A	0.9600	C38—C39	1.514 (11)
C12—H12B	0.9600	C38—H38	0.9800
C12—H12C	0.9600	C39—O11'	1.4096 (11)
C13—N2	1.294 (6)	C39—O11	1.4108 (11)
C13—H13	0.9300	C39—H39A	0.9700
C14—N2	1.455 (6)	C39—H39B	0.9700
C14—C16	1.485 (9)	C40—C41	1.460 (12)
C14—C15	1.541 (11)	C40—C42	1.531 (17)
C14—H14	0.9800	C40—H40	0.9800
C15—O5	1.417 (7)	C41—H41A	0.9600
C15—H15A	0.9700	C41—H41B	0.9600
C15—H15B	0.9700	C41—H41C	0.9600
C16—C17	1.513 (11)	C42—H42A	0.9600
C16—C18	1.543 (14)	C42—H42B	0.9600
C16—H16	0.9800	C42—H42C	0.9600
C17—H17A	0.9600	C43—N6	1.314 (7)
C17—H17B	0.9600	C43—H43	0.9300
C17—H17C	0.9600	C44—N6	1.449 (6)
C18—H18A	0.9600	C44—C45	1.506 (10)
C18—H18B	0.9600	C44—C46	1.521 (9)
C18—H18C	0.9600	C44—H44	0.9800
C19—N3	1.283 (6)	C45—O12	1.396 (8)
C19—H19	0.9300	C45—H45A	0.9700
C20—N3	1.472 (6)	C45—H45B	0.9700
C20—C21	1.506 (8)	C46—C48	1.508 (17)
C20—C22	1.533 (8)	C46—C47	1.517 (16)
C20—H20	0.9800	C46—H46	0.9800
C21—O6	1.411 (8)	C47—H47A	0.9600
C21—H21A	0.9700	C47—H47B	0.9600
C21—H21B	0.9700	C47—H47C	0.9600
C22—C24	1.519 (8)	C48—H48A	0.9600
C22—C23	1.528 (10)	C48—H48B	0.9600
C22—H22	0.9800	C48—H48C	0.9600
C23—H23A	0.9600	N1—H1N	0.834 (10)
C23—H23B	0.9600	N2—H2N	0.827 (11)
C23—H23C	0.9600	N3—H3N	0.823 (10)
C24—H24A	0.9600	N4—H4N	0.83 (5)
C24—H24B	0.9600	N5—H5N	0.831 (10)
C24—H24C	0.9600	N6—H6N	0.830 (10)
C25—O7	1.272 (5)	O4—H4	0.8200
C25—C26	1.428 (6)	O5—H5	0.8200
C25—C30	1.462 (6)	O6—H6	0.8200
C26—C31	1.404 (7)	O10—H10A	0.8200
C26—C27	1.430 (6)	O11—H11	0.8200
C27—O8	1.270 (5)	O11'—H11'	0.8200
C27—C28	1.438 (7)	O12—H12	0.8200

O1—C1—C6	121.6 (4)	C43—C30—C29	117.9 (4)
O1—C1—C2	120.0 (4)	C43—C30—C25	121.2 (4)
C6—C1—C2	118.3 (3)	C29—C30—C25	120.9 (4)
C7—C2—C3	120.6 (4)	N4—C31—C26	126.6 (4)
C7—C2—C1	117.3 (4)	N4—C31—H31	116.7
C3—C2—C1	122.1 (4)	C26—C31—H31	116.7
O2—C3—C2	121.2 (4)	N4—C32—C33	108.7 (5)
O2—C3—C4	121.3 (4)	N4—C32—C34	110.1 (5)
C2—C3—C4	117.6 (4)	C33—C32—C34	115.4 (5)
C13—C4—C5	121.2 (4)	N4—C32—H32	107.4
C13—C4—C3	117.5 (4)	C33—C32—H32	107.4
C5—C4—C3	121.3 (4)	C34—C32—H32	107.4
O3—C5—C4	119.9 (4)	O10—C33—C32	109.3 (5)
O3—C5—C6	120.6 (4)	O10—C33—H33A	109.8
C4—C5—C6	119.5 (4)	C32—C33—H33A	109.8
C19—C6—C1	120.6 (4)	O10—C33—H33B	109.8
C19—C6—C5	118.2 (4)	C32—C33—H33B	109.8
C1—C6—C5	121.1 (4)	H33A—C33—H33B	108.3
N1—C7—C2	127.0 (4)	C35—C34—C36	116.8 (7)
N1—C7—H7	116.5	C35—C34—C32	110.5 (5)
C2—C7—H7	116.5	C36—C34—C32	109.9 (7)
N1—C8—C10	112.4 (4)	C35—C34—H34	106.3
N1—C8—C9	109.5 (4)	C36—C34—H34	106.3
C10—C8—C9	112.6 (4)	C32—C34—H34	106.3
N1—C8—H8	107.3	C34—C35—H35A	109.5
C10—C8—H8	107.3	C34—C35—H35B	109.5
C9—C8—H8	107.3	H35A—C35—H35B	109.5
O4—C9—C8	112.3 (4)	C34—C35—H35C	109.5
O4—C9—H9A	109.1	H35A—C35—H35C	109.5
C8—C9—H9A	109.1	H35B—C35—H35C	109.5
O4—C9—H9B	109.1	C34—C36—H36A	109.5
C8—C9—H9B	109.1	C34—C36—H36B	109.5
H9A—C9—H9B	107.9	H36A—C36—H36B	109.5
C11—C10—C8	111.6 (4)	C34—C36—H36C	109.5
C11—C10—C12	110.1 (5)	H36A—C36—H36C	109.5
C8—C10—C12	113.5 (5)	H36B—C36—H36C	109.5
C11—C10—H10	107.1	N5—C37—C28	124.5 (5)
C8—C10—H10	107.1	N5—C37—H37	117.7
C12—C10—H10	107.1	C28—C37—H37	117.7
C10—C11—H11A	109.5	N5—C38—C40	111.7 (6)
C10—C11—H11B	109.5	N5—C38—C39	108.6 (6)
H11A—C11—H11B	109.5	C40—C38—C39	115.7 (6)
C10—C11—H11C	109.5	N5—C38—H38	106.8
H11A—C11—H11C	109.5	C40—C38—H38	106.8
H11B—C11—H11C	109.5	C39—C38—H38	106.8
C10—C12—H12A	109.5	O11'—C39—O11	34.9 (8)
C10—C12—H12B	109.5	O11'—C39—C38	140.3 (12)
H12A—C12—H12B	109.5	O11—C39—C38	109.2 (7)
C10—C12—H12C	109.5	O11'—C39—H39A	101.8
H12A—C12—H12C	109.5	O11—C39—H39A	109.8
H12B—C12—H12C	109.5	C38—C39—H39A	109.8
N2—C13—C4	124.6 (4)	O11'—C39—H39B	81.2
N2—C13—H13	117.7	O11—C39—H39B	109.8
C4—C13—H13	117.7	C38—C39—H39B	109.8
N2—C14—C16	112.8 (5)	H39A—C39—H39B	108.3
N2—C14—C15	108.5 (5)	C41—C40—C38	114.0 (9)
C16—C14—C15	112.0 (6)	C41—C40—C42	114.1 (8)
N2—C14—H14	107.8	C38—C40—C42	111.1 (9)
C16—C14—H14	107.8	C41—C40—H40	105.6
C15—C14—H14	107.8	C38—C40—H40	105.6
O5—C15—C14	112.4 (6)	C42—C40—H40	105.6
O5—C15—H15A	109.1	C40—C41—H41A	109.5
C14—C15—H15A	109.1	C40—C41—H41B	109.5
O5—C15—H15B	109.1	H41A—C41—H41B	109.5
C14—C15—H15B	109.1	C40—C41—H41C	109.5
H15A—C15—H15B	107.9	H41A—C41—H41C	109.5
C14—C16—C17	114.3 (6)	H41B—C41—H41C	109.5
C14—C16—C18	109.5 (7)	C40—C42—H42A	109.5
C17—C16—C18	111.9 (8)	C40—C42—H42B	109.5
C14—C16—H16	106.9	H42A—C42—H42B	109.5
C17—C16—H16	106.9	C40—C42—H42C	109.5
C18—C16—H16	106.9	H42A—C42—H42C	109.5
C16—C17—H17A	109.5	H42B—C42—H42C	109.5
C16—C17—H17B	109.5	N6—C43—C30	126.8 (5)
H17A—C17—H17B	109.5	N6—C43—H43	116.6
C16—C17—H17C	109.5	C30—C43—H43	116.6
H17A—C17—H17C	109.5	N6—C44—C45	110.0 (5)
H17B—C17—H17C	109.5	N6—C44—C46	110.4 (5)
C16—C18—H18A	109.5	C45—C44—C46	113.5 (6)
C16—C18—H18B	109.5	N6—C44—H44	107.6
H18A—C18—H18B	109.5	C45—C44—H44	107.6
C16—C18—H18C	109.5	C46—C44—H44	107.6
H18A—C18—H18C	109.5	O12—C45—C44	112.0 (6)
H18B—C18—H18C	109.5	O12—C45—H45A	109.2
N3—C19—C6	127.1 (4)	C44—C45—H45A	109.2
N3—C19—H19	116.5	O12—C45—H45B	109.2
C6—C19—H19	116.5	C44—C45—H45B	109.2
N3—C20—C21	109.6 (4)	H45A—C45—H45B	107.9
N3—C20—C22	110.1 (5)	C48—C46—C47	114.0 (10)
C21—C20—C22	114.1 (4)	C48—C46—C44	109.1 (7)
N3—C20—H20	107.6	C47—C46—C44	112.0 (9)
C21—C20—H20	107.6	C48—C46—H46	107.2
C22—C20—H20	107.6	C47—C46—H46	107.2
O6—C21—C20	111.5 (5)	C44—C46—H46	107.2
O6—C21—H21A	109.3	C46—C47—H47A	109.5
C20—C21—H21A	109.3	C46—C47—H47B	109.5
O6—C21—H21B	109.3	H47A—C47—H47B	109.5
C20—C21—H21B	109.3	C46—C47—H47C	109.5
H21A—C21—H21B	108.0	H47A—C47—H47C	109.5
C24—C22—C23	109.8 (6)	H47B—C47—H47C	109.5
C24—C22—C20	112.7 (6)	C46—C48—H48A	109.5
C23—C22—C20	110.5 (5)	C46—C48—H48B	109.5
C24—C22—H22	107.9	H48A—C48—H48B	109.5
C23—C22—H22	107.9	C46—C48—H48C	109.5
C20—C22—H22	107.9	H48A—C48—H48C	109.5
C22—C23—H23A	109.5	H48B—C48—H48C	109.5
C22—C23—H23B	109.5	C7—N1—C8	124.4 (4)
H23A—C23—H23B	109.5	C7—N1—H1N	116 (4)
C22—C23—H23C	109.5	C8—N1—H1N	120 (4)
H23A—C23—H23C	109.5	C13—N2—C14	126.3 (5)
H23B—C23—H23C	109.5	C13—N2—H2N	112 (4)
C22—C24—H24A	109.5	C14—N2—H2N	122 (4)
C22—C24—H24B	109.5	C19—N3—C20	126.4 (4)
H24A—C24—H24B	109.5	C19—N3—H3N	125 (3)
C22—C24—H24C	109.5	C20—N3—H3N	109 (3)
H24A—C24—H24C	109.5	C31—N4—C32	125.6 (4)
H24B—C24—H24C	109.5	C31—N4—H4N	122 (4)
O7—C25—C26	121.7 (4)	C32—N4—H4N	112 (4)
O7—C25—C30	119.7 (4)	C37—N5—C38	125.5 (5)
C26—C25—C30	118.6 (4)	C37—N5—H5N	122 (4)
C31—C26—C25	117.3 (4)	C38—N5—H5N	112 (4)
C31—C26—C27	120.7 (4)	C43—N6—C44	126.2 (5)
C25—C26—C27	121.9 (4)	C43—N6—H6N	120 (4)
O8—C27—C26	119.7 (4)	C44—N6—H6N	113 (4)
O8—C27—C28	121.3 (4)	C9—O4—H4	109.5
C26—C27—C28	119.1 (4)	C15—O5—H5	109.5
C37—C28—C27	117.8 (4)	C21—O6—H6	109.5
C37—C28—C29	120.8 (4)	C33—O10—H10A	109.5
C27—C28—C29	121.2 (4)	C39—O11—H11	109.5
O9—C29—C30	120.9 (4)	C39—O11'—H11'	109.5
O9—C29—C28	120.8 (4)	C45—O12—H12	109.5
C30—C29—C28	118.3 (4)

O1—C1—C2—C7	−1.1 (6)	O8—C27—C28—C29	−176.9 (5)
C6—C1—C2—C7	177.8 (4)	C26—C27—C28—C29	2.5 (7)
O1—C1—C2—C3	179.3 (4)	C37—C28—C29—O9	1.4 (7)
C6—C1—C2—C3	−1.8 (6)	C27—C28—C29—O9	177.7 (5)
C7—C2—C3—O2	−0.3 (6)	C37—C28—C29—C30	−179.3 (5)
C1—C2—C3—O2	179.3 (4)	C27—C28—C29—C30	−3.0 (7)
C7—C2—C3—C4	179.9 (4)	O9—C29—C30—C43	−0.7 (7)
C1—C2—C3—C4	−0.5 (6)	C28—C29—C30—C43	−180.0 (4)
O2—C3—C4—C13	0.8 (6)	O9—C29—C30—C25	−179.1 (5)
C2—C3—C4—C13	−179.4 (4)	C28—C29—C30—C25	1.6 (6)
O2—C3—C4—C5	−177.0 (4)	O7—C25—C30—C43	1.1 (7)
C2—C3—C4—C5	2.8 (6)	C26—C25—C30—C43	−178.1 (5)
C13—C4—C5—O3	−0.2 (7)	O7—C25—C30—C29	179.4 (4)
C3—C4—C5—O3	177.5 (4)	C26—C25—C30—C29	0.3 (6)
C13—C4—C5—C6	179.6 (5)	C25—C26—C31—N4	−174.0 (5)
C3—C4—C5—C6	−2.7 (7)	C27—C26—C31—N4	2.7 (7)
O1—C1—C6—C19	3.1 (7)	N4—C32—C33—O10	−63.1 (6)
C2—C1—C6—C19	−175.8 (4)	C34—C32—C33—O10	61.1 (7)
O1—C1—C6—C5	−179.2 (4)	N4—C32—C34—C35	−60.8 (7)
C2—C1—C6—C5	1.9 (6)	C33—C32—C34—C35	175.7 (6)
O3—C5—C6—C19	−2.2 (7)	N4—C32—C34—C36	168.9 (6)
C4—C5—C6—C19	178.0 (4)	C33—C32—C34—C36	45.4 (9)
O3—C5—C6—C1	−179.9 (4)	C27—C28—C37—N5	−176.2 (5)
C4—C5—C6—C1	0.3 (7)	C29—C28—C37—N5	0.3 (8)
C3—C2—C7—N1	−0.2 (7)	N5—C38—C39—O11'	48.6 (18)
C1—C2—C7—N1	−179.8 (4)	C40—C38—C39—O11'	175.1 (16)
N1—C8—C9—O4	61.4 (5)	N5—C38—C39—O11	68.7 (8)
C10—C8—C9—O4	−172.7 (4)	C40—C38—C39—O11	−164.8 (8)
N1—C8—C10—C11	−60.5 (6)	N5—C38—C40—C41	59.8 (9)
C9—C8—C10—C11	175.1 (5)	C39—C38—C40—C41	−65.1 (10)
N1—C8—C10—C12	64.5 (6)	N5—C38—C40—C42	−70.7 (10)
C9—C8—C10—C12	−59.8 (6)	C39—C38—C40—C42	164.4 (9)
C5—C4—C13—N2	−1.2 (8)	C29—C30—C43—N6	−178.5 (5)
C3—C4—C13—N2	−179.0 (5)	C25—C30—C43—N6	0.0 (8)
N2—C14—C15—O5	60.9 (7)	N6—C44—C45—O12	64.0 (7)
C16—C14—C15—O5	−173.9 (5)	C46—C44—C45—O12	−171.8 (6)
N2—C14—C16—C17	51.7 (9)	N6—C44—C46—C48	61.3 (9)
C15—C14—C16—C17	−71.0 (8)	C45—C44—C46—C48	−62.7 (9)
N2—C14—C16—C18	−74.7 (8)	N6—C44—C46—C47	−65.8 (10)
C15—C14—C16—C18	162.7 (7)	C45—C44—C46—C47	170.2 (7)
C1—C6—C19—N3	−0.5 (8)	C2—C7—N1—C8	174.3 (4)
C5—C6—C19—N3	−178.3 (5)	C10—C8—N1—C7	139.4 (5)
N3—C20—C21—O6	68.4 (6)	C9—C8—N1—C7	−94.6 (5)
C22—C20—C21—O6	−167.6 (4)	C4—C13—N2—C14	176.5 (6)
N3—C20—C22—C24	176.6 (5)	C16—C14—N2—C13	135.7 (7)
C21—C20—C22—C24	52.9 (7)	C15—C14—N2—C13	−99.7 (7)
N3—C20—C22—C23	−60.1 (6)	C6—C19—N3—C20	177.0 (5)
C21—C20—C22—C23	176.1 (5)	C21—C20—N3—C19	−106.9 (6)
O7—C25—C26—C31	−3.2 (7)	C22—C20—N3—C19	126.8 (6)
C30—C25—C26—C31	176.0 (4)	C26—C31—N4—C32	174.6 (5)
O7—C25—C26—C27	−179.9 (4)	C33—C32—N4—C31	−109.9 (6)
C30—C25—C26—C27	−0.8 (6)	C34—C32—N4—C31	122.8 (6)
C31—C26—C27—O8	2.2 (7)	C28—C37—N5—C38	177.6 (6)
C25—C26—C27—O8	178.8 (5)	C40—C38—N5—C37	124.0 (7)
C31—C26—C27—C28	−177.2 (4)	C39—C38—N5—C37	−107.3 (7)
C25—C26—C27—C28	−0.6 (7)	C30—C43—N6—C44	174.7 (5)
O8—C27—C28—C37	−0.5 (7)	C45—C44—N6—C43	−99.9 (7)
C26—C27—C28—C37	178.9 (5)	C46—C44—N6—C43	134.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O7	0.82	2.09	2.726 (5)	135
O5—H5···O9	0.82	2.14	2.822 (6)	141
O6—H6···O8	0.82	1.96	2.652 (5)	142
O10—H10A···O6ⁱ	0.82	2.03	2.793 (7)	156
O11—H11···O3	0.82	2.01	2.806 (10)	163
O12—H12···O2	0.82	2.05	2.716 (5)	138
N1—H1N···O2	0.83 (1)	2.03 (5)	2.658 (5)	132 (6)
N2—H2N···O3	0.83 (1)	1.89 (4)	2.591 (5)	142 (6)
N3—H3N···O1	0.82 (1)	2.12 (4)	2.656 (5)	122 (3)
N4—H4N···O8	0.83 (5)	2.06 (5)	2.625 (6)	125 (5)
N5—H5N···O9	0.83 (1)	2.04 (5)	2.622 (6)	127 (5)
N6—H6N···O7	0.83 (1)	2.04 (4)	2.636 (5)	128 (4)

Symmetry code: (i) −x+2, y−1/2, −z+1.

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