(8S)-3-(2-De­oxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranos­yl)-3,6,7,8-tetra­hydro­imidazo[4,5-d][1,3]diazepin-8-ol

In the asymmetric unit of the title compound, C₂₇H₂₈N₄O₆, there are two independent mol­ecules which have different conformations. The tetra­hydro­furan and dihydro­diazepine rings adopt envelope conformations. The hydr­oxy, amino and carbonyl groups are all involved in hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.060
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C15    -   C16     ..       9.84 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N14    -   C9      ..       5.38 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.36 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C46

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           27.50
           From the CIF: _reflns_number_total               5949
           Count of symmetry unique reflns         5978
           Completeness (_total/calc)             99.51%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C37    = .          S

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(8S)-3-(2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentafuranosyl)-3,6,7,8- tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol

Crystal data

C27H28N4O6	F(000) = 1064.00
Mr = 504.54	Dx = 1.346 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 17822 reflections
a = 10.492 (2) Å	θ = 3.1–27.5°
b = 12.849 (3) Å	µ = 0.10 mm^−1
c = 18.645 (5) Å	T = 296 K
β = 97.949 (10)°	Block, yellow
V = 2489.5 (10) Å^3	0.30 × 0.14 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.044
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −13→13
24329 measured reflections	k = −16→14
5949 independent reflections	l = −24→24
2974 reflections with F^2 > 2σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.8800σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max = 0.001
wR(F^2) = 0.060	Δρmax = 0.32 e Å^−3
S = 1.00	Δρmin = −0.34 e Å^−3
5949 reflections	Extinction correction: Larson (1970), equation 22
668 parameters	Extinction coefficient: 198 (9)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O11	0.96716 (18)	0.20321 (16)	0.66926 (12)	0.0585 (7)
O12	0.47114 (18)	0.23973 (16)	0.42713 (12)	0.0624 (7)
O13	1.19551 (18)	0.16255 (14)	0.83206 (12)	0.0600 (7)
O14	1.2378 (2)	−0.00561 (18)	0.85454 (13)	0.0828 (9)
O15	0.95671 (18)	0.39923 (14)	0.74725 (12)	0.0589 (6)
O16	1.1353 (2)	0.45454 (18)	0.81589 (13)	0.0807 (8)
O31	0.63294 (18)	0.44869 (17)	0.77241 (12)	0.0589 (7)
O32	1.13683 (19)	0.42174 (18)	0.97601 (13)	0.0837 (8)
O33	0.3350 (2)	0.47436 (16)	0.64957 (12)	0.0727 (7)
O34	0.3013 (2)	0.63669 (18)	0.60881 (13)	0.0764 (8)
O35	0.49218 (16)	0.25511 (13)	0.79300 (11)	0.0523 (6)
O36	0.3560 (2)	0.20670 (17)	0.69525 (12)	0.0659 (7)
N11	0.7472 (2)	0.23195 (17)	0.63411 (13)	0.0487 (7)
N12	0.6291 (2)	0.34647 (18)	0.56604 (13)	0.0544 (8)
N13	0.4752 (2)	0.0376 (2)	0.51081 (16)	0.0693 (9)
N14	0.6563 (2)	0.06925 (17)	0.59959 (14)	0.0580 (8)
N31	0.7159 (2)	0.42978 (17)	0.89433 (12)	0.0490 (7)
N32	0.8466 (2)	0.32321 (18)	0.96247 (14)	0.0616 (8)
N33	1.0223 (2)	0.6330 (2)	0.97668 (17)	0.0726 (9)
N34	0.8270 (2)	0.58956 (19)	0.90004 (17)	0.0638 (9)
C1	1.0552 (2)	0.2312 (2)	0.73190 (17)	0.0520 (9)
C2	0.9761 (2)	0.2949 (2)	0.77739 (17)	0.0500 (9)
C3	0.8462 (2)	0.2417 (2)	0.76393 (17)	0.0525 (9)
C4	0.8426 (2)	0.1896 (2)	0.69022 (18)	0.0508 (10)
C5	0.7295 (2)	0.3334 (2)	0.61574 (19)	0.0606 (10)
C6	0.5786 (2)	0.2474 (2)	0.55138 (17)	0.0446 (8)
C7	0.4570 (2)	0.2308 (2)	0.50151 (18)	0.0499 (10)
C8	0.3955 (2)	0.1286 (2)	0.51761 (18)	0.0605 (10)
C9	0.5781 (3)	0.0120 (2)	0.5587 (2)	0.0654 (11)
C10	0.6508 (2)	0.1762 (2)	0.59256 (18)	0.0476 (9)
C11	1.1063 (2)	0.1317 (2)	0.77019 (19)	0.0614 (10)
C12	1.2571 (2)	0.0835 (2)	0.8704 (2)	0.0590 (11)
C13	1.3503 (2)	0.1238 (2)	0.93117 (19)	0.0540 (10)
C14	1.4539 (3)	0.0611 (2)	0.95753 (19)	0.0703 (12)
C15	1.5466 (3)	0.1009 (3)	1.0112 (2)	0.0836 (15)
C16	1.5359 (3)	0.1968 (3)	1.0406 (2)	0.0748 (13)
C17	1.4303 (2)	0.2558 (2)	1.0161 (2)	0.0724 (12)
C18	1.3384 (2)	0.2203 (2)	0.96101 (19)	0.0629 (11)
C19	1.6402 (3)	0.2368 (3)	1.0989 (2)	0.1142 (17)
C20	1.0422 (2)	0.4728 (2)	0.7722 (2)	0.0595 (11)
C21	1.0049 (2)	0.5766 (2)	0.7427 (2)	0.0574 (10)
C22	1.0823 (3)	0.6593 (2)	0.7640 (2)	0.0923 (15)
C23	1.0488 (3)	0.7598 (3)	0.7422 (2)	0.0994 (16)
C24	0.9374 (3)	0.7784 (2)	0.6964 (2)	0.0771 (14)
C25	0.8641 (4)	0.6963 (2)	0.6730 (2)	0.0934 (15)
C26	0.8959 (3)	0.5954 (2)	0.6963 (2)	0.0877 (14)
C27	0.8954 (4)	0.8884 (2)	0.6758 (2)	0.1107 (18)
C31	0.5152 (2)	0.4157 (2)	0.72914 (18)	0.0513 (9)
C32	0.4426 (2)	0.3613 (2)	0.78191 (17)	0.0485 (9)
C33	0.4782 (2)	0.4198 (2)	0.85171 (17)	0.0531 (9)
C34	0.6089 (2)	0.4694 (2)	0.84441 (18)	0.0501 (9)
C35	0.7359 (2)	0.3321 (2)	0.92122 (18)	0.0568 (10)
C36	0.9023 (2)	0.4204 (2)	0.96306 (18)	0.0522 (9)
C37	1.0280 (2)	0.4459 (2)	1.0088 (2)	0.0603 (11)
C38	1.0290 (3)	0.5576 (2)	1.03415 (19)	0.0697 (12)
C39	0.9214 (2)	0.6494 (2)	0.9256 (2)	0.0689 (11)
C40	0.8236 (2)	0.4879 (2)	0.92164 (18)	0.0505 (10)
C41	0.4483 (2)	0.5128 (2)	0.6958 (2)	0.0696 (12)
C42	0.2690 (2)	0.5464 (2)	0.60837 (19)	0.0594 (11)
C43	0.1546 (2)	0.5032 (2)	0.56332 (19)	0.0551 (10)
C44	0.0800 (2)	0.5671 (2)	0.5159 (2)	0.0767 (12)
C45	−0.0282 (3)	0.5293 (3)	0.4739 (2)	0.0788 (13)
C46	−0.0644 (2)	0.4280 (2)	0.47740 (19)	0.0633 (11)
C47	0.0108 (3)	0.3640 (2)	0.5248 (2)	0.0800 (13)
C48	0.1198 (3)	0.4004 (2)	0.5677 (2)	0.0722 (12)
C49	−0.1803 (2)	0.3858 (2)	0.4283 (2)	0.0907 (14)
C50	0.4403 (2)	0.1841 (2)	0.74359 (18)	0.0507 (10)
C51	0.4952 (2)	0.0792 (2)	0.75763 (18)	0.0508 (10)
C52	0.4388 (3)	−0.0024 (2)	0.7162 (2)	0.0705 (12)
C53	0.4853 (3)	−0.1012 (2)	0.7270 (2)	0.0802 (14)
C54	0.5882 (3)	−0.1234 (2)	0.7791 (2)	0.0704 (13)
C55	0.6442 (3)	−0.0420 (2)	0.8195 (2)	0.0714 (12)
C56	0.5983 (2)	0.0582 (2)	0.8096 (2)	0.0599 (11)
C57	0.6398 (4)	−0.2337 (2)	0.7905 (2)	0.1058 (17)
H1	1.1262	0.2728	0.7180	0.062*
H2	1.0124	0.2956	0.8287	0.060*
H4	0.8263	0.1150	0.6953	0.061*
H5	0.7820	0.3872	0.6358	0.073*
H7	0.3976	0.2859	0.5118	0.060*
H9	0.5950	−0.0590	0.5626	0.079*
H14	1.4613	−0.0060	0.9398	0.084*
H15	1.6183	0.0605	1.0274	0.100*
H17	1.4201	0.3206	1.0366	0.087*
H18	1.2682	0.2620	0.9442	0.075*
H22	1.1596	0.6479	0.7938	0.111*
H23	1.1022	0.8150	0.7588	0.119*
H25	0.7899	0.7071	0.6404	0.112*
H26	0.8419	0.5404	0.6798	0.105*
H31	0.8384	0.1904	0.8012	0.063*
H32	0.7773	0.2923	0.7629	0.063*
H34	0.6029	0.5449	0.8510	0.060*
H35	0.6776	0.2777	0.9114	0.068*
H37	1.0327	0.4025	1.0523	0.072*
H39	0.9188	0.7154	0.9050	0.083*
H44	0.1027	0.6366	0.5121	0.092*
H45	−0.0778	0.5741	0.4422	0.095*
H47	−0.0121	0.2944	0.5281	0.096*
H48	0.1694	0.3556	0.5994	0.087*
H52	0.3689	0.0102	0.6809	0.085*
H53	0.4465	−0.1549	0.6985	0.096*
H55	0.7148	−0.0548	0.8544	0.086*
H56	0.6371	0.1118	0.8381	0.072*
H81	0.3756	0.1311	0.5668	0.073*
H82	0.3165	0.1208	0.4843	0.073*
H111	1.0360	0.0923	0.7856	0.074*
H112	1.1497	0.0894	0.7379	0.074*
H121	0.5405	0.2019	0.4176	0.074*
H130	0.4553	−0.0022	0.4739	0.083*
H191	1.6439	0.3114	1.0964	0.137*
H192	1.7218	0.2082	1.0914	0.137*
H193	1.6207	0.2163	1.1457	0.137*
H271	0.8436	0.9150	0.7103	0.133*
H272	0.8460	0.8884	0.6285	0.133*
H273	0.9699	0.9318	0.6757	0.133*
H301	0.5338	0.3675	0.6912	0.062*
H302	0.3496	0.3622	0.7661	0.058*
H321	1.1378	0.4615	0.9355	0.098*
H330	1.0892	0.6709	0.9750	0.087*
H331	0.4856	0.3727	0.8927	0.064*
H332	0.4146	0.4728	0.8574	0.064*
H381	1.1078	0.5695	1.0669	0.084*
H382	0.9556	0.5681	1.0598	0.084*
H411	0.5041	0.5504	0.6675	0.083*
H412	0.4237	0.5581	0.7332	0.083*
H491	−0.1909	0.4233	0.3833	0.109*
H492	−0.2560	0.3939	0.4514	0.109*
H493	−0.1673	0.3133	0.4191	0.109*
H571	0.6250	−0.2712	0.7456	0.127*
H572	0.5966	−0.2682	0.8259	0.127*
H573	0.7305	−0.2313	0.8073	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0493 (12)	0.0720 (14)	0.0514 (15)	0.0074 (10)	−0.0029 (11)	−0.0072 (11)
O12	0.0678 (13)	0.0651 (13)	0.0505 (16)	0.0025 (11)	−0.0053 (11)	0.0065 (12)
O13	0.0590 (12)	0.0472 (12)	0.0666 (16)	0.0070 (10)	−0.0169 (12)	0.0063 (10)
O14	0.1001 (18)	0.0513 (15)	0.091 (2)	0.0155 (13)	−0.0072 (15)	0.0042 (14)
O15	0.0608 (12)	0.0452 (12)	0.0642 (16)	0.0030 (10)	−0.0144 (11)	−0.0008 (11)
O16	0.0653 (13)	0.0719 (16)	0.094 (2)	−0.0031 (12)	−0.0284 (14)	0.0022 (14)
O31	0.0453 (11)	0.0703 (14)	0.0577 (16)	−0.0051 (10)	−0.0054 (11)	0.0086 (12)
O32	0.0576 (13)	0.0821 (16)	0.105 (2)	0.0214 (12)	−0.0125 (13)	−0.0097 (15)
O33	0.0666 (13)	0.0545 (13)	0.0847 (19)	−0.0061 (10)	−0.0324 (13)	0.0191 (12)
O34	0.0697 (14)	0.0528 (14)	0.099 (2)	−0.0031 (11)	−0.0143 (13)	0.0168 (14)
O35	0.0532 (11)	0.0410 (10)	0.0587 (15)	0.0004 (9)	−0.0065 (11)	−0.0027 (10)
O36	0.0640 (13)	0.0636 (14)	0.0642 (17)	0.0006 (11)	−0.0125 (13)	−0.0086 (12)
N11	0.0451 (13)	0.0364 (14)	0.0592 (19)	0.0007 (11)	−0.0118 (13)	0.0055 (12)
N12	0.0587 (15)	0.0400 (14)	0.059 (2)	0.0013 (12)	−0.0119 (14)	0.0017 (13)
N13	0.088 (2)	0.0506 (16)	0.062 (2)	−0.0156 (15)	−0.0139 (17)	−0.0088 (15)
N14	0.0602 (16)	0.0337 (14)	0.074 (2)	−0.0060 (12)	−0.0130 (15)	0.0007 (14)
N31	0.0477 (13)	0.0376 (14)	0.0572 (19)	−0.0009 (11)	−0.0089 (13)	0.0003 (12)
N32	0.0663 (17)	0.0419 (15)	0.068 (2)	0.0005 (12)	−0.0208 (15)	0.0027 (14)
N33	0.0562 (16)	0.0581 (16)	0.096 (2)	−0.0106 (14)	−0.0161 (17)	−0.0003 (18)
N34	0.0617 (16)	0.0385 (15)	0.085 (2)	−0.0050 (13)	−0.0137 (15)	0.0047 (14)
C1	0.0459 (17)	0.0549 (19)	0.052 (2)	0.0028 (14)	−0.0054 (16)	−0.0009 (17)
C2	0.0572 (19)	0.0486 (18)	0.041 (2)	0.0062 (15)	−0.0062 (16)	0.0039 (15)
C3	0.0485 (16)	0.0591 (19)	0.048 (2)	0.0025 (15)	0.0022 (15)	0.0048 (17)
C4	0.0495 (18)	0.0470 (18)	0.053 (2)	0.0003 (14)	−0.0023 (17)	0.0079 (16)
C5	0.0590 (19)	0.0411 (18)	0.075 (2)	−0.0059 (15)	−0.0156 (19)	0.0030 (17)
C6	0.0440 (15)	0.0362 (15)	0.051 (2)	−0.0013 (13)	−0.0038 (15)	0.0054 (15)
C7	0.0521 (18)	0.0434 (18)	0.051 (2)	0.0013 (14)	−0.0055 (17)	−0.0042 (16)
C8	0.0537 (17)	0.0599 (19)	0.063 (2)	−0.0134 (16)	−0.0077 (17)	−0.0026 (18)
C9	0.079 (2)	0.0443 (19)	0.068 (2)	−0.0090 (17)	−0.007 (2)	0.0082 (18)
C10	0.0474 (17)	0.0370 (17)	0.055 (2)	−0.0071 (14)	−0.0034 (17)	−0.0029 (15)
C11	0.0524 (18)	0.0578 (19)	0.070 (2)	0.0039 (16)	−0.0076 (18)	0.0035 (19)
C12	0.0556 (19)	0.056 (2)	0.066 (2)	0.0160 (17)	0.0129 (18)	0.017 (2)
C13	0.0524 (18)	0.059 (2)	0.051 (2)	0.0093 (16)	0.0069 (16)	0.0164 (18)
C14	0.072 (2)	0.074 (2)	0.064 (2)	0.0305 (19)	0.007 (2)	0.020 (2)
C15	0.061 (2)	0.121 (3)	0.067 (3)	0.030 (2)	0.002 (2)	0.044 (2)
C16	0.065 (2)	0.091 (2)	0.067 (3)	−0.003 (2)	0.002 (2)	0.020 (2)
C17	0.070 (2)	0.079 (2)	0.066 (2)	−0.002 (2)	−0.002 (2)	0.006 (2)
C18	0.0574 (19)	0.061 (2)	0.068 (2)	0.0088 (17)	0.0030 (18)	0.0174 (19)
C19	0.084 (2)	0.173 (4)	0.077 (3)	−0.025 (2)	−0.017 (2)	0.019 (3)
C20	0.0512 (19)	0.057 (2)	0.067 (2)	−0.0019 (17)	−0.0028 (19)	−0.0047 (18)
C21	0.0574 (19)	0.0479 (19)	0.065 (2)	−0.0051 (16)	0.0033 (19)	−0.0062 (17)
C22	0.078 (2)	0.067 (2)	0.122 (4)	−0.012 (2)	−0.023 (2)	0.010 (2)
C23	0.092 (2)	0.061 (2)	0.140 (4)	−0.026 (2)	−0.001 (3)	0.001 (2)
C24	0.087 (2)	0.060 (2)	0.088 (3)	0.005 (2)	0.025 (2)	0.002 (2)
C25	0.118 (3)	0.054 (2)	0.097 (3)	0.005 (2)	−0.029 (2)	−0.002 (2)
C26	0.101 (2)	0.049 (2)	0.100 (3)	0.006 (2)	−0.035 (2)	−0.010 (2)
C27	0.127 (3)	0.052 (2)	0.160 (4)	0.010 (2)	0.047 (3)	0.023 (2)
C31	0.0445 (16)	0.0529 (19)	0.053 (2)	−0.0027 (15)	−0.0067 (16)	0.0051 (17)
C32	0.0387 (15)	0.0480 (18)	0.056 (2)	0.0042 (13)	−0.0047 (15)	−0.0016 (16)
C33	0.0490 (16)	0.0499 (17)	0.059 (2)	0.0023 (14)	0.0012 (15)	−0.0077 (16)
C34	0.0495 (17)	0.0391 (17)	0.057 (2)	−0.0006 (13)	−0.0098 (17)	0.0030 (15)
C35	0.067 (2)	0.0354 (16)	0.064 (2)	−0.0093 (15)	−0.0070 (19)	−0.0035 (16)
C36	0.0570 (18)	0.0461 (18)	0.050 (2)	−0.0004 (15)	−0.0071 (17)	0.0003 (16)
C37	0.054 (2)	0.058 (2)	0.063 (2)	0.0046 (16)	−0.0121 (18)	0.0029 (18)
C38	0.065 (2)	0.067 (2)	0.071 (2)	−0.0046 (18)	−0.009 (2)	−0.014 (2)
C39	0.061 (2)	0.0457 (19)	0.095 (3)	−0.0033 (16)	−0.007 (2)	−0.0007 (19)
C40	0.0454 (17)	0.0442 (19)	0.058 (2)	−0.0013 (14)	−0.0076 (17)	−0.0016 (16)
C41	0.064 (2)	0.059 (2)	0.077 (2)	−0.0080 (17)	−0.022 (2)	0.0115 (18)
C42	0.0523 (18)	0.056 (2)	0.066 (2)	0.0054 (17)	−0.0032 (18)	0.0121 (19)
C43	0.0474 (18)	0.055 (2)	0.060 (2)	0.0041 (15)	−0.0033 (16)	0.0161 (17)
C44	0.067 (2)	0.052 (2)	0.103 (3)	0.0023 (17)	−0.018 (2)	0.014 (2)
C45	0.065 (2)	0.080 (2)	0.082 (3)	0.008 (2)	−0.022 (2)	0.019 (2)
C46	0.0568 (19)	0.072 (2)	0.058 (2)	−0.0015 (18)	−0.0028 (18)	0.002 (2)
C47	0.087 (2)	0.059 (2)	0.085 (3)	−0.0189 (19)	−0.017 (2)	0.014 (2)
C48	0.075 (2)	0.057 (2)	0.076 (2)	−0.0058 (18)	−0.018 (2)	0.0210 (19)
C49	0.069 (2)	0.101 (3)	0.093 (3)	−0.004 (2)	−0.021 (2)	−0.005 (2)
C50	0.0522 (18)	0.0510 (19)	0.048 (2)	−0.0086 (15)	0.0046 (18)	−0.0032 (17)
C51	0.0536 (18)	0.0472 (18)	0.053 (2)	−0.0054 (15)	0.0106 (17)	−0.0012 (17)
C52	0.089 (2)	0.051 (2)	0.068 (2)	−0.0038 (19)	−0.002 (2)	−0.0103 (19)
C53	0.111 (3)	0.053 (2)	0.073 (3)	−0.008 (2)	0.000 (2)	−0.015 (2)
C54	0.089 (2)	0.045 (2)	0.081 (3)	0.0059 (19)	0.025 (2)	0.003 (2)
C55	0.066 (2)	0.058 (2)	0.087 (3)	0.0077 (18)	−0.000 (2)	0.008 (2)
C56	0.0551 (19)	0.053 (2)	0.070 (2)	−0.0072 (16)	0.0021 (19)	0.0029 (19)
C57	0.139 (3)	0.054 (2)	0.130 (4)	0.019 (2)	0.039 (3)	0.008 (2)

Geometric parameters (Å, º)

O11—C1	1.431 (3)	C44—C45	1.376 (4)
O11—C4	1.426 (3)	C45—C46	1.359 (5)
O12—C7	1.420 (4)	C46—C47	1.375 (4)
O13—C11	1.437 (3)	C46—C49	1.518 (4)
O13—C12	1.354 (3)	C47—C48	1.384 (4)
O14—C12	1.193 (4)	C50—C51	1.475 (4)
O15—C2	1.456 (3)	C51—C52	1.385 (4)
O15—C20	1.341 (3)	C51—C56	1.375 (4)
O16—C20	1.205 (3)	C52—C53	1.365 (4)
O31—C31	1.442 (3)	C53—C54	1.379 (5)
O31—C34	1.425 (4)	C54—C55	1.373 (5)
O32—C37	1.402 (4)	C54—C57	1.522 (4)
O33—C41	1.455 (3)	C55—C56	1.378 (4)
O33—C42	1.335 (3)	O12—H121	0.913
O34—C42	1.208 (4)	O32—H321	0.913
O35—C32	1.465 (3)	N13—H130	0.860
O35—C50	1.356 (3)	N33—H330	0.860
O36—C50	1.207 (3)	C1—H1	0.980
N11—C4	1.450 (3)	C2—H2	0.980
N11—C5	1.354 (3)	C3—H31	0.970
N11—C10	1.385 (3)	C3—H32	0.970
N12—C5	1.314 (3)	C4—H4	0.980
N12—C6	1.392 (3)	C5—H5	0.930
N13—C8	1.452 (3)	C7—H7	0.980
N13—C9	1.344 (4)	C8—H81	0.970
N14—C9	1.274 (3)	C8—H82	0.970
N14—C10	1.382 (3)	C9—H9	0.930
N31—C34	1.448 (3)	C11—H111	0.970
N31—C35	1.357 (3)	C11—H112	0.970
N31—C40	1.391 (3)	C14—H14	0.930
N32—C35	1.306 (3)	C15—H15	0.930
N32—C36	1.378 (3)	C17—H17	0.930
N33—C38	1.438 (4)	C18—H18	0.930
N33—C39	1.339 (4)	C19—H191	0.960
N34—C39	1.292 (3)	C19—H192	0.960
N34—C40	1.368 (3)	C19—H193	0.960
C1—C2	1.508 (4)	C22—H22	0.930
C1—C11	1.526 (4)	C23—H23	0.930
C2—C3	1.515 (3)	C25—H25	0.930
C3—C4	1.525 (4)	C26—H26	0.930
C6—C7	1.486 (3)	C27—H271	0.960
C6—C10	1.356 (3)	C27—H272	0.960
C7—C8	1.512 (4)	C27—H273	0.960
C12—C13	1.484 (4)	C31—H301	0.980
C13—C14	1.388 (4)	C32—H302	0.980
C13—C18	1.371 (4)	C33—H331	0.970
C14—C15	1.392 (4)	C33—H332	0.970
C15—C16	1.359 (6)	C34—H34	0.980
C16—C17	1.368 (4)	C35—H35	0.930
C16—C19	1.522 (5)	C37—H37	0.980
C17—C18	1.385 (4)	C38—H381	0.970
C20—C21	1.475 (4)	C38—H382	0.970
C21—C22	1.362 (4)	C39—H39	0.930
C21—C26	1.358 (4)	C41—H411	0.970
C22—C23	1.384 (5)	C41—H412	0.970
C23—C24	1.370 (5)	C44—H44	0.930
C24—C25	1.342 (5)	C45—H45	0.930
C24—C27	1.514 (5)	C47—H47	0.930
C25—C26	1.393 (5)	C48—H48	0.930
C31—C32	1.498 (4)	C49—H491	0.960
C31—C41	1.522 (4)	C49—H492	0.960
C32—C33	1.504 (4)	C49—H493	0.960
C33—C34	1.536 (3)	C52—H52	0.930
C36—C37	1.505 (4)	C53—H53	0.930
C36—C40	1.362 (4)	C55—H55	0.930
C37—C38	1.511 (4)	C56—H56	0.930
C42—C43	1.475 (4)	C57—H571	0.960
C43—C44	1.369 (4)	C57—H572	0.960
C43—C48	1.376 (4)	C57—H573	0.960
O11···C47	3.474 (4)	H25···H82	2.676
O12···O34	2.889 (3)	H25···H121	3.486
O12···C9	3.552 (3)	H25···H571	2.803
O13···O35	3.501 (2)	H25···H573	3.351
O13···O36	3.295 (3)	H26···O31	3.198
O13···C50	3.250 (3)	H26···H82	3.432
O14···C52	3.550 (4)	H26···H411	3.522
O15···O31	3.550 (2)	H31···N32	3.449
O16···O32	3.013 (3)	H31···C35	3.185
O16···C32	3.578 (3)	H31···C56	3.060
O16···C33	3.595 (3)	H31···H35	3.048
O31···O15	3.550 (2)	H31···H55	3.598
O31···C3	3.493 (3)	H31···H56	2.521
O31···C5	3.546 (4)	H31···H381	2.897
O32···O16	3.013 (3)	H31···H382	3.509
O32···C18	3.379 (3)	H32···O31	2.537
O34···O12	2.889 (3)	H32···O35	3.155
O34···C49	3.477 (4)	H32···N31	3.158
O35···O13	3.501 (2)	H32···C31	3.161
O35···C13	3.572 (4)	H32···C34	3.369
O36···O13	3.295 (3)	H32···C35	3.084
O36···C1	3.335 (3)	H32···H35	3.097
O36···C8	3.540 (4)	H32···H56	3.175
O36···C11	3.280 (4)	H32···H301	2.882
N12···N13	2.975 (3)	H34···C15	3.271
N12···C31	3.531 (4)	H34···C16	3.291
N12···C49	3.503 (4)	H34···C57	3.105
N13···N12	2.975 (3)	H34···H15	3.467
N14···C27	3.567 (4)	H34···H193	3.224
N14···C51	3.596 (4)	H34···H571	3.103
N14···C52	3.487 (4)	H34···H572	2.446
N32···N33	2.954 (3)	H34···H573	3.322
N33···N32	2.954 (3)	H35···C3	3.500
N34···C57	3.475 (4)	H35···C15	3.350
C1···O36	3.335 (3)	H35···C16	3.176
C3···O31	3.493 (3)	H35···C17	3.467
C3···C35	3.496 (4)	H35···H31	3.048
C5···O31	3.546 (4)	H35···H32	3.097
C5···C31	3.458 (4)	H35···H191	3.543
C8···O36	3.540 (4)	H35···H192	3.442
C9···O12	3.552 (3)	H35···H330	3.305
C9···C52	3.462 (5)	H35···H381	3.485
C11···O36	3.280 (4)	H37···N33	3.540
C12···C50	3.495 (5)	H37···C39	3.305
C12···C51	3.482 (4)	H37···H39	2.562
C13···O35	3.572 (4)	H37···H55	3.013
C14···C56	3.326 (5)	H37···H330	3.251
C15···C33	3.494 (5)	H39···O32	3.557
C18···O32	3.379 (3)	H39···N32	3.522
C25···C57	3.545 (6)	H39···C22	3.409
C27···N14	3.567 (4)	H39···C23	3.541
C31···N12	3.531 (4)	H39···C37	3.380
C31···C5	3.458 (4)	H39···C57	3.438
C32···O16	3.578 (3)	H39···H22	3.589
C33···O16	3.595 (3)	H39···H37	2.562
C33···C15	3.494 (5)	H39···H572	3.503
C35···C3	3.496 (4)	H39···H573	2.588
C47···O11	3.474 (4)	H44···O11	3.467
C49···O34	3.477 (4)	H44···N11	3.550
C49···N12	3.503 (4)	H44···N14	3.597
C50···O13	3.250 (3)	H44···C10	3.487
C50···C12	3.495 (5)	H44···C47	3.194
C51···N14	3.596 (4)	H44···C49	3.449
C51···C12	3.482 (4)	H44···H47	2.319
C52···O14	3.550 (4)	H44···H493	2.649
C52···N14	3.487 (4)	H45···O11	3.015
C52···C9	3.462 (5)	H45···C8	3.585
C56···C14	3.326 (5)	H45···H47	3.010
C57···N34	3.475 (4)	H45···H81	3.191
C57···C25	3.545 (6)	H45···H82	3.076
O11···H44	3.467	H45···H112	3.345
O11···H45	3.015	H45···H273	3.186
O11···H47	2.916	H47···O11	2.916
O11···H48	3.286	H47···N11	3.508
O11···H273	3.490	H47···C5	3.390
O12···H9	2.692	H47···C44	3.091
O12···H25	2.882	H47···C45	3.434
O12···H53	2.937	H47···H5	3.365
O12···H411	3.037	H47···H44	2.319
O12···H492	3.460	H47···H45	3.010
O12···H571	3.242	H48···O11	3.286
O13···H302	3.355	H48···C1	3.303
O13···H382	2.990	H48···H1	2.551
O14···H23	3.134	H48···H7	3.207
O14···H191	2.755	H52···N13	3.522
O14···H382	2.909	H52···C8	3.449
O16···H302	2.812	H52···C9	3.376
O16···H321	2.229	H52···C49	3.083
O16···H332	2.935	H52···H9	3.568
O31···H5	3.264	H52···H81	2.642
O31···H26	3.198	H52···H112	2.851
O31···H32	2.537	H52···H491	2.356
O32···H2	3.299	H52···H492	2.985
O32···H15	3.135	H53···O12	2.937
O32···H17	3.297	H53···O34	3.403
O32···H18	2.586	H53···C49	3.441
O32···H39	3.557	H53···H9	3.385
O32···H55	3.340	H53···H121	2.858
O33···H121	3.504	H53···H193	3.499
O33···H130	3.410	H53···H491	3.066
O34···H53	3.403	H53···H492	3.264
O34···H121	1.981	H53···H493	3.432
O34···H492	3.502	H55···O32	3.340
O34···H493	2.682	H55···C37	3.448
O35···H32	3.155	H55···C38	3.477
O36···H1	2.646	H55···H14	3.342
O36···H81	2.618	H55···H17	3.080
O36···H112	2.840	H55···H31	3.598
N11···H44	3.550	H55···H37	3.013
N11···H47	3.508	H55···H271	3.193
N11···H301	3.137	H55···H381	2.722
N12···H9	3.347	H56···C3	3.218
N12···H130	2.222	H56···C14	3.203
N12···H301	2.676	H56···C15	3.490
N12···H411	3.585	H56···H4	3.535
N12···H492	2.667	H56···H14	3.202
N13···H7	3.546	H56···H31	2.521
N13···H52	3.522	H56···H32	3.175
N13···H411	3.365	H56···H381	3.046
N13···H492	3.106	H81···O36	2.618
N14···H44	3.597	H81···C50	3.342
N14···H271	3.306	H81···C52	3.260
N14···H272	3.059	H81···H45	3.191
N31···H32	3.158	H81···H52	2.642
N32···H2	3.251	H81···H491	3.499
N32···H31	3.449	H81···H492	3.295
N32···H39	3.522	H82···C25	3.406
N32···H191	3.501	H82···C45	3.435
N32···H192	3.248	H82···H25	2.676
N32···H330	2.329	H82···H26	3.432
N32···H381	3.352	H82···H45	3.076
N33···H37	3.540	H82···H492	3.248
N33···H192	3.271	H111···C27	3.520
N34···H572	3.189	H111···C38	3.549
N34···H573	2.972	H111···H271	3.234
C1···H48	3.303	H111···H273	2.923
C1···H302	3.498	H111···H381	3.327
C3···H35	3.500	H111···H382	2.889
C3···H56	3.218	H112···O36	2.840
C4···H271	3.548	H112···C50	3.271
C4···H273	3.596	H112···C51	3.595
C5···H47	3.390	H112···C52	3.330
C5···H130	3.181	H112···H23	3.590
C5···H301	2.681	H112···H45	3.345
C5···H492	3.186	H112···H52	2.851
C6···H9	3.600	H112···H273	2.899
C6···H130	3.264	H112···H491	3.181
C6···H301	3.120	H121···O33	3.504
C6···H492	3.307	H121···O34	1.981
C7···H9	2.974	H121···C41	3.233
C7···H25	3.451	H121···C42	2.914
C7···H130	3.565	H121···H9	3.427
C8···H25	3.449	H121···H25	3.486
C8···H45	3.585	H121···H53	2.858
C8···H52	3.449	H121···H411	2.513
C8···H492	3.435	H121···H412	3.428
C9···H7	3.214	H121···H492	3.268
C9···H52	3.376	H121···H493	3.381
C9···H272	3.332	H121···H571	3.306
C10···H44	3.487	H130···O33	3.410
C10···H301	3.399	H130···N12	2.222
C11···H273	3.325	H130···C5	3.181
C11···H382	3.422	H130···C6	3.264
C12···H382	2.741	H130···C7	3.565
C13···H382	3.316	H130···C41	3.458
C14···H17	3.356	H130···C42	3.513
C14···H56	3.203	H130···H5	3.316
C14···H191	3.475	H130···H7	3.123
C15···H34	3.271	H130···H301	3.520
C15···H35	3.350	H130···H411	2.810
C15···H56	3.490	H130···H492	2.983
C15···H331	3.477	H191···O14	2.755
C15···H332	2.933	H191···N32	3.501
C16···H34	3.291	H191···C14	3.475
C16···H35	3.176	H191···C35	3.543
C16···H331	3.548	H191···H14	2.641
C16···H332	3.448	H191···H22	3.418
C16···H572	3.047	H191···H23	3.520
C17···H14	3.329	H191···H35	3.543
C17···H35	3.467	H191···H572	3.243
C17···H331	2.872	H192···N32	3.248
C17···H572	3.014	H192···N33	3.271
C18···H331	2.896	H192···C22	3.219
C19···H14	3.516	H192···C35	3.571
C19···H22	2.925	H192···H22	2.448
C19···H330	3.428	H192···H23	3.415
C19···H332	3.554	H192···H35	3.442
C19···H572	3.017	H192···H321	3.559
C20···H302	3.541	H192···H330	2.524
C20···H321	3.075	H192···H332	3.533
C22···H39	3.409	H193···C22	3.411
C22···H192	3.219	H193···C54	3.444
C22···H193	3.411	H193···C57	3.194
C23···H39	3.541	H193···H22	2.576
C23···H493	3.479	H193···H23	3.435
C24···H493	3.478	H193···H34	3.224
C24···H571	3.580	H193···H53	3.499
C24···H573	3.199	H193···H332	3.150
C25···H82	3.406	H193···H412	3.121
C25···H571	3.039	H193···H571	3.497
C25···H573	3.172	H193···H572	2.418
C26···H571	3.547	H271···N14	3.306
C27···H4	3.034	H271···C4	3.548
C27···H111	3.520	H271···C54	3.165
C27···H491	3.461	H271···C55	3.163
C27···H573	3.540	H271···C57	3.367
C31···H5	3.513	H271···H4	2.589
C31···H32	3.161	H271···H9	3.537
C32···H1	3.555	H271···H55	3.193
C33···H15	3.163	H271···H111	3.234
C34···H32	3.369	H271···H571	3.439
C34···H572	3.389	H271···H573	2.966
C35···H31	3.185	H272···N14	3.059
C35···H32	3.084	H272···C9	3.332
C35···H191	3.543	H272···C45	3.403
C35···H192	3.571	H272···C46	3.265
C35···H330	3.228	H272···C47	3.422
C36···H2	3.314	H272···H4	3.186
C36···H330	3.404	H272···H9	2.830
C37···H39	3.380	H273···O11	3.490
C37···H55	3.448	H273···C4	3.596
C38···H55	3.477	H273···C11	3.325
C38···H111	3.549	H273···C45	3.192
C39···H37	3.305	H273···C46	3.149
C39···H573	3.163	H273···C49	3.188
C41···H121	3.233	H273···H4	2.846
C41···H130	3.458	H273···H45	3.186
C41···H571	3.395	H273···H111	2.923
C42···H121	2.914	H273···H112	2.899
C42···H130	3.513	H273···H491	2.703
C44···H47	3.091	H273···H493	3.277
C44···H493	3.466	H301···N11	3.137
C45···H47	3.434	H301···N12	2.676
C45···H82	3.435	H301···C5	2.681
C45···H272	3.403	H301···C6	3.120
C45···H273	3.192	H301···C10	3.399
C46···H5	3.594	H301···H5	2.942
C46···H272	3.265	H301···H32	2.882
C46···H273	3.149	H301···H130	3.520
C47···H5	3.393	H302···O13	3.355
C47···H44	3.194	H302···O16	2.812
C47···H272	3.422	H302···C1	3.498
C48···H1	3.240	H302···C20	3.541
C48···H7	3.547	H302···H1	2.652
C49···H44	3.449	H321···O16	2.229
C49···H52	3.083	H321···C20	3.075
C49···H53	3.441	H321···H2	3.085
C49···H273	3.188	H321···H15	2.855
C50···H1	3.457	H321···H18	2.899
C50···H81	3.342	H321···H22	3.597
C50···H112	3.271	H321···H192	3.559
C51···H112	3.595	H321···H332	3.427
C52···H9	3.566	H330···N32	2.329
C52···H81	3.260	H330···C19	3.428
C52···H112	3.330	H330···C35	3.228
C52···H491	3.129	H330···C36	3.404
C53···H9	3.462	H330···H15	3.387
C53···H491	3.481	H330···H22	3.568
C54···H17	3.523	H330···H35	3.305
C54···H193	3.444	H330···H37	3.251
C54···H271	3.165	H330···H192	2.524
C55···H14	3.181	H331···C15	3.477
C55···H17	3.356	H331···C16	3.548
C55···H271	3.163	H331···C17	2.872
C55···H381	3.432	H331···C18	2.896
C56···H4	3.494	H331···H14	3.466
C56···H14	3.099	H331···H15	3.111
C56···H31	3.060	H331···H17	2.938
C56···H381	3.588	H331···H18	2.958
C57···H17	3.439	H332···O16	2.935
C57···H25	3.480	H332···C15	2.933
C57···H34	3.105	H332···C16	3.448
C57···H39	3.438	H332···C19	3.554
C57···H193	3.194	H332···H15	2.490
C57···H271	3.367	H332···H22	3.570
C57···H412	3.574	H332···H192	3.533
H1···O36	2.646	H332···H193	3.150
H1···C32	3.555	H332···H321	3.427
H1···C48	3.240	H381···N32	3.352
H1···C50	3.457	H381···C55	3.432
H1···H48	2.551	H381···C56	3.588
H1···H302	2.652	H381···H15	3.573
H2···O32	3.299	H381···H31	2.897
H2···N32	3.251	H381···H35	3.485
H2···C36	3.314	H381···H55	2.722
H2···H321	3.085	H381···H56	3.046
H2···H382	3.575	H381···H111	3.327
H4···C27	3.034	H382···O13	2.990
H4···C56	3.494	H382···O14	2.909
H4···H56	3.535	H382···C11	3.422
H4···H271	2.589	H382···C12	2.741
H4···H272	3.186	H382···C13	3.316
H4···H273	2.846	H382···H2	3.575
H5···O31	3.264	H382···H18	3.418
H5···C31	3.513	H382···H31	3.509
H5···C46	3.594	H382···H111	2.889
H5···C47	3.393	H411···O12	3.037
H5···H47	3.365	H411···N12	3.585
H5···H130	3.316	H411···N13	3.365
H5···H301	2.942	H411···H26	3.522
H5···H492	3.408	H411···H121	2.513
H7···N13	3.546	H411···H130	2.810
H7···C9	3.214	H411···H571	2.911
H7···C48	3.547	H412···C57	3.574
H7···H9	2.436	H412···H22	3.339
H7···H25	3.377	H412···H121	3.428
H7···H48	3.207	H412···H193	3.121
H7···H130	3.123	H412···H571	3.032
H9···O12	2.692	H412···H572	3.224
H9···N12	3.347	H491···C27	3.461
H9···C6	3.600	H491···C52	3.129
H9···C7	2.974	H491···C53	3.481
H9···C52	3.566	H491···H23	3.243
H9···C53	3.462	H491···H52	2.356
H9···H7	2.436	H491···H53	3.066
H9···H52	3.568	H491···H81	3.499
H9···H53	3.385	H491···H112	3.181
H9···H121	3.427	H491···H273	2.703
H9···H271	3.537	H492···O12	3.460
H9···H272	2.830	H492···O34	3.502
H9···H492	3.582	H492···N12	2.667
H14···C17	3.329	H492···N13	3.106
H14···C19	3.516	H492···C5	3.186
H14···C55	3.181	H492···C6	3.307
H14···C56	3.099	H492···C8	3.435
H14···H17	2.560	H492···H5	3.408
H14···H55	3.342	H492···H9	3.582
H14···H56	3.202	H492···H52	2.985
H14···H191	2.641	H492···H53	3.264
H14···H331	3.466	H492···H81	3.295
H15···O32	3.135	H492···H82	3.248
H15···C33	3.163	H492···H121	3.268
H15···H17	3.310	H492···H130	2.983
H15···H34	3.467	H493···O34	2.682
H15···H321	2.855	H493···C23	3.479
H15···H330	3.387	H493···C24	3.478
H15···H331	3.111	H493···C44	3.466
H15···H332	2.490	H493···H23	3.478
H15···H381	3.573	H493···H44	2.649
H17···O32	3.297	H493···H53	3.432
H17···C14	3.356	H493···H121	3.381
H17···C54	3.523	H493···H273	3.277
H17···C55	3.356	H571···O12	3.242
H17···C57	3.439	H571···C24	3.580
H17···H14	2.560	H571···C25	3.039
H17···H15	3.310	H571···C26	3.547
H17···H55	3.080	H571···C41	3.395
H17···H331	2.938	H571···H25	2.803
H17···H572	2.833	H571···H34	3.103
H17···H573	3.562	H571···H121	3.306
H18···O32	2.586	H571···H193	3.497
H18···H321	2.899	H571···H271	3.439
H18···H331	2.958	H571···H411	2.911
H18···H382	3.418	H571···H412	3.032
H22···C19	2.925	H572···N34	3.189
H22···H39	3.589	H572···C16	3.047
H22···H191	3.418	H572···C17	3.014
H22···H192	2.448	H572···C19	3.017
H22···H193	2.576	H572···C34	3.389
H22···H321	3.597	H572···H17	2.833
H22···H330	3.568	H572···H34	2.446
H22···H332	3.570	H572···H39	3.503
H22···H412	3.339	H572···H191	3.243
H23···O14	3.134	H572···H193	2.418
H23···H112	3.590	H572···H412	3.224
H23···H191	3.520	H573···N34	2.972
H23···H192	3.415	H573···C24	3.199
H23···H193	3.435	H573···C25	3.172
H23···H491	3.243	H573···C27	3.540
H23···H493	3.478	H573···C39	3.163
H25···O12	2.882	H573···H17	3.562
H25···C7	3.451	H573···H25	3.351
H25···C8	3.449	H573···H34	3.322
H25···C57	3.480	H573···H39	2.588
H25···H7	3.377	H573···H271	2.966
C1—O11—C4	108.7 (2)	C38—N33—H330	117.0
C11—O13—C12	115.3 (2)	C39—N33—H330	117.0
C2—O15—C20	117.6 (2)	O11—C1—H1	110.5
C31—O31—C34	109.4 (2)	C2—C1—H1	110.5
C41—O33—C42	115.0 (2)	C11—C1—H1	110.5
C32—O35—C50	115.4 (2)	O15—C2—H2	112.6
C4—N11—C5	126.9 (2)	C1—C2—H2	112.6
C4—N11—C10	126.0 (2)	C3—C2—H2	112.6
C5—N11—C10	107.0 (2)	C2—C3—H31	110.6
C5—N12—C6	105.5 (2)	C2—C3—H32	110.6
C8—N13—C9	123.9 (2)	C4—C3—H31	110.6
C9—N14—C10	120.2 (2)	C4—C3—H32	110.6
C34—N31—C35	129.0 (2)	H31—C3—H32	109.5
C34—N31—C40	124.4 (2)	O11—C4—H4	109.0
C35—N31—C40	106.6 (2)	N11—C4—H4	109.0
C35—N32—C36	105.5 (2)	C3—C4—H4	109.0
C38—N33—C39	126.1 (2)	N11—C5—H5	124.1
C39—N34—C40	120.6 (2)	N12—C5—H5	124.1
O11—C1—C2	104.6 (2)	O12—C7—H7	106.8
O11—C1—C11	108.4 (2)	C6—C7—H7	106.8
C2—C1—C11	112.2 (2)	C8—C7—H7	106.8
O15—C2—C1	109.9 (2)	N13—C8—H81	108.2
O15—C2—C3	106.1 (2)	N13—C8—H82	108.2
C1—C2—C3	102.4 (2)	C7—C8—H81	108.2
C2—C3—C4	104.9 (2)	C7—C8—H82	108.2
O11—C4—N11	108.9 (2)	H81—C8—H82	109.5
O11—C4—C3	106.5 (2)	N13—C9—H9	114.8
N11—C4—C3	114.4 (2)	N14—C9—H9	114.8
N11—C5—N12	111.7 (2)	O13—C11—H111	110.1
N12—C6—C7	121.6 (2)	O13—C11—H112	110.1
N12—C6—C10	109.7 (2)	C1—C11—H111	110.1
C7—C6—C10	128.5 (2)	C1—C11—H112	110.1
O12—C7—C6	113.8 (2)	H111—C11—H112	109.5
O12—C7—C8	111.7 (2)	C13—C14—H14	120.8
C6—C7—C8	110.7 (2)	C15—C14—H14	120.8
N13—C8—C7	114.5 (2)	C14—C15—H15	118.8
N13—C9—N14	130.4 (2)	C16—C15—H15	118.8
N11—C10—N14	116.3 (2)	C16—C17—H17	119.5
N11—C10—C6	106.0 (2)	C18—C17—H17	119.5
N14—C10—C6	137.5 (2)	C13—C18—H18	119.8
O13—C11—C1	107.0 (2)	C17—C18—H18	119.8
O13—C12—O14	122.5 (2)	C16—C19—H191	109.5
O13—C12—C13	110.9 (2)	C16—C19—H192	109.5
O14—C12—C13	126.6 (3)	C16—C19—H193	109.5
C12—C13—C14	118.0 (3)	H191—C19—H192	109.5
C12—C13—C18	122.5 (2)	H191—C19—H193	109.5
C14—C13—C18	119.5 (2)	H192—C19—H193	109.5
C13—C14—C15	118.4 (3)	C21—C22—H22	119.1
C14—C15—C16	122.4 (3)	C23—C22—H22	119.1
C15—C16—C17	118.4 (3)	C22—C23—H23	119.8
C15—C16—C19	120.3 (3)	C24—C23—H23	119.8
C17—C16—C19	121.4 (3)	C24—C25—H25	119.0
C16—C17—C18	120.9 (3)	C26—C25—H25	119.0
C13—C18—C17	120.3 (2)	C21—C26—H26	119.7
O15—C20—O16	122.5 (2)	C25—C26—H26	119.7
O15—C20—C21	112.2 (2)	C24—C27—H271	109.5
O16—C20—C21	125.2 (2)	C24—C27—H272	109.5
C20—C21—C22	118.7 (2)	C24—C27—H273	109.5
C20—C21—C26	123.7 (2)	H271—C27—H272	109.5
C22—C21—C26	117.5 (3)	H271—C27—H273	109.5
C21—C22—C23	121.7 (3)	H272—C27—H273	109.5
C22—C23—C24	120.4 (3)	O31—C31—H301	110.5
C23—C24—C25	117.8 (3)	C32—C31—H301	110.5
C23—C24—C27	121.0 (3)	C41—C31—H301	110.5
C25—C24—C27	121.2 (3)	O35—C32—H302	111.9
C24—C25—C26	121.9 (3)	C31—C32—H302	111.9
C21—C26—C25	120.5 (3)	C33—C32—H302	111.9
O31—C31—C32	104.1 (2)	C32—C33—H331	110.7
O31—C31—C41	107.4 (2)	C32—C33—H332	110.7
C32—C31—C41	113.8 (2)	C34—C33—H331	110.7
O35—C32—C31	108.9 (2)	C34—C33—H332	110.7
O35—C32—C33	107.6 (2)	H331—C33—H332	109.5
C31—C32—C33	104.4 (2)	O31—C34—H34	109.0
C32—C33—C34	104.4 (2)	N31—C34—H34	109.0
O31—C34—N31	108.5 (2)	C33—C34—H34	109.0
O31—C34—C33	106.4 (2)	N31—C35—H35	123.9
N31—C34—C33	114.8 (2)	N32—C35—H35	123.9
N31—C35—N32	112.2 (2)	O32—C37—H37	106.5
N32—C36—C37	122.7 (2)	C36—C37—H37	106.5
N32—C36—C40	110.5 (2)	C38—C37—H37	106.5
C37—C36—C40	126.7 (2)	N33—C38—H381	108.3
O32—C37—C36	114.1 (2)	N33—C38—H382	108.3
O32—C37—C38	112.1 (2)	C37—C38—H381	108.3
C36—C37—C38	110.6 (2)	C37—C38—H382	108.3
N33—C38—C37	114.1 (2)	H381—C38—H382	109.5
N33—C39—N34	131.2 (3)	N33—C39—H39	114.4
N31—C40—N34	117.3 (2)	N34—C39—H39	114.4
N31—C40—C36	105.2 (2)	O33—C41—H411	110.6
N34—C40—C36	137.5 (2)	O33—C41—H412	110.6
O33—C41—C31	104.9 (2)	C31—C41—H411	110.6
O33—C42—O34	122.6 (2)	C31—C41—H412	110.6
O33—C42—C43	112.5 (2)	H411—C41—H412	109.5
O34—C42—C43	124.8 (2)	C43—C44—H44	119.7
C42—C43—C44	119.3 (2)	C45—C44—H44	119.7
C42—C43—C48	121.9 (2)	C44—C45—H45	119.2
C44—C43—C48	118.7 (2)	C46—C45—H45	119.2
C43—C44—C45	120.6 (3)	C46—C47—H47	119.2
C44—C45—C46	121.6 (3)	C48—C47—H47	119.2
C45—C46—C47	117.7 (2)	C43—C48—H48	120.2
C45—C46—C49	121.3 (3)	C47—C48—H48	120.2
C47—C46—C49	121.0 (3)	C46—C49—H491	109.5
C46—C47—C48	121.6 (3)	C46—C49—H492	109.5
C43—C48—C47	119.7 (3)	C46—C49—H493	109.5
O35—C50—O36	122.0 (2)	H491—C49—H492	109.5
O35—C50—C51	112.6 (2)	H491—C49—H493	109.5
O36—C50—C51	125.4 (2)	H492—C49—H493	109.5
C50—C51—C52	117.8 (2)	C51—C52—H52	119.8
C50—C51—C56	123.7 (2)	C53—C52—H52	119.8
C52—C51—C56	118.5 (2)	C52—C53—H53	119.2
C51—C52—C53	120.4 (3)	C54—C53—H53	119.2
C52—C53—C54	121.7 (3)	C54—C55—H55	119.2
C53—C54—C55	117.6 (3)	C56—C55—H55	119.2
C53—C54—C57	121.4 (3)	C51—C56—H56	119.8
C55—C54—C57	121.0 (3)	C55—C56—H56	119.8
C54—C55—C56	121.5 (3)	C54—C57—H571	109.5
C51—C56—C55	120.3 (3)	C54—C57—H572	109.5
C7—O12—H121	110.0	C54—C57—H573	109.5
C37—O32—H321	109.8	H571—C57—H572	109.5
C8—N13—H130	118.0	H571—C57—H573	109.5
C9—N13—H130	118.0	H572—C57—H573	109.5
C1—O11—C4—N11	140.7 (2)	C6—C7—C8—N13	−59.6 (3)
C1—O11—C4—C3	16.9 (2)	O13—C12—C13—C14	−155.2 (3)
C4—O11—C1—C2	−33.5 (2)	O14—C12—C13—C18	−157.6 (3)
C4—O11—C1—C11	86.4 (2)	C12—C13—C14—C15	175.7 (3)
C11—O13—C12—O14	−0.7 (4)	C12—C13—C18—C17	−177.9 (3)
C11—O13—C12—C13	177.7 (2)	C14—C13—C18—C17	1.3 (5)
C12—O13—C11—C1	−176.1 (2)	C18—C13—C14—C15	−3.5 (5)
C2—O15—C20—O16	2.8 (4)	C13—C14—C15—C16	3.0 (6)
C2—O15—C20—C21	−174.4 (2)	C14—C15—C16—C17	−0.3 (5)
C20—O15—C2—C1	−91.8 (3)	C14—C15—C16—C19	−179.8 (3)
C20—O15—C2—C3	158.2 (2)	C15—C16—C17—C18	−2.0 (5)
C31—O31—C34—N31	139.3 (2)	C19—C16—C17—C18	177.5 (3)
C31—O31—C34—C33	15.3 (2)	C16—C17—C18—C13	1.5 (5)
C34—O31—C31—C32	−30.9 (2)	O15—C20—C21—C22	179.3 (3)
C34—O31—C31—C41	90.0 (2)	O15—C20—C21—C26	0.6 (5)
C41—O33—C42—O34	0.7 (4)	O16—C20—C21—C22	2.2 (5)
C41—O33—C42—C43	−179.4 (2)	O16—C20—C21—C26	−176.5 (3)
C42—O33—C41—C31	−172.9 (2)	C20—C21—C22—C23	−175.6 (4)
C32—O35—C50—O36	−2.3 (4)	C20—C21—C26—C25	177.3 (3)
C32—O35—C50—C51	179.5 (2)	C22—C21—C26—C25	−1.5 (6)
C50—O35—C32—C31	−84.7 (2)	C26—C21—C22—C23	3.2 (6)
C50—O35—C32—C33	162.8 (2)	C21—C22—C23—C24	−2.1 (7)
C4—N11—C5—N12	−175.5 (2)	C22—C23—C24—C25	−0.9 (7)
C5—N11—C4—O11	−68.0 (3)	C22—C23—C24—C27	176.2 (4)
C5—N11—C4—C3	50.9 (4)	C23—C24—C25—C26	2.6 (7)
C4—N11—C10—N14	−8.2 (4)	C27—C24—C25—C26	−174.5 (4)
C4—N11—C10—C6	175.4 (2)	C24—C25—C26—C21	−1.4 (6)
C10—N11—C4—O11	116.9 (3)	O31—C31—C32—O35	−81.0 (2)
C10—N11—C4—C3	−124.1 (3)	O31—C31—C32—C33	33.7 (2)
C5—N11—C10—N14	175.9 (2)	O31—C31—C41—O33	176.6 (2)
C5—N11—C10—C6	−0.5 (3)	C32—C31—C41—O33	−68.7 (3)
C10—N11—C5—N12	0.3 (3)	C41—C31—C32—O35	162.5 (2)
C5—N12—C6—C7	175.2 (3)	C41—C31—C32—C33	−82.8 (2)
C5—N12—C6—C10	−0.4 (3)	O35—C32—C33—C34	91.3 (2)
C6—N12—C5—N11	0.1 (2)	C31—C32—C33—C34	−24.3 (2)
C8—N13—C9—N14	−29.8 (6)	C32—C33—C34—O31	6.3 (2)
C9—N13—C8—C7	73.6 (4)	C32—C33—C34—N31	−113.7 (2)
C9—N14—C10—N11	−173.8 (3)	N32—C36—C37—O32	85.9 (3)
C9—N14—C10—C6	1.1 (6)	N32—C36—C37—C38	−146.6 (3)
C10—N14—C9—N13	−7.7 (5)	N32—C36—C40—N31	−0.3 (3)
C34—N31—C35—N32	176.9 (2)	N32—C36—C40—N34	−177.3 (3)
C35—N31—C34—O31	−85.1 (3)	C37—C36—C40—N31	−175.7 (3)
C35—N31—C34—C33	33.8 (4)	C37—C36—C40—N34	7.3 (6)
C34—N31—C40—N34	0.6 (4)	C40—C36—C37—O32	−99.2 (3)
C34—N31—C40—C36	−177.1 (2)	C40—C36—C37—C38	28.3 (4)
C40—N31—C34—O31	91.9 (3)	O32—C37—C38—N33	64.0 (3)
C40—N31—C34—C33	−149.3 (2)	C36—C37—C38—N33	−64.5 (3)
C35—N31—C40—N34	178.2 (2)	O13—C12—C13—C18	24.0 (4)
C35—N31—C40—C36	0.5 (3)	O14—C12—C13—C14	23.2 (5)
C40—N31—C35—N32	−0.5 (3)	O33—C42—C43—C44	−177.4 (3)
C35—N32—C36—C37	175.7 (3)	O33—C42—C43—C48	3.0 (4)
C35—N32—C36—C40	0.0 (2)	O34—C42—C43—C44	2.5 (5)
C36—N32—C35—N31	0.3 (3)	O34—C42—C43—C48	−177.0 (3)
C38—N33—C39—N34	−23.7 (6)	C42—C43—C44—C45	−179.2 (3)
C39—N33—C38—C37	67.4 (4)	C42—C43—C48—C47	179.3 (3)
C39—N34—C40—N31	177.0 (3)	C44—C43—C48—C47	−0.3 (5)
C39—N34—C40—C36	−6.2 (6)	C48—C43—C44—C45	0.4 (5)
C40—N34—C39—N33	−4.8 (6)	C43—C44—C45—C46	−0.4 (6)
O11—C1—C2—O15	−76.7 (2)	C44—C45—C46—C47	0.1 (4)
O11—C1—C2—C3	35.7 (2)	C44—C45—C46—C49	−177.1 (3)
O11—C1—C11—O13	179.2 (2)	C45—C46—C47—C48	0.0 (5)
C2—C1—C11—O13	−65.8 (3)	C49—C46—C47—C48	177.2 (3)
C11—C1—C2—O15	166.0 (2)	C46—C47—C48—C43	0.1 (4)
C11—C1—C2—C3	−81.6 (2)	O35—C50—C51—C52	172.2 (3)
O15—C2—C3—C4	90.1 (2)	O35—C50—C51—C56	−7.4 (4)
C1—C2—C3—C4	−25.2 (2)	O36—C50—C51—C52	−5.9 (5)
C2—C3—C4—O11	6.2 (2)	O36—C50—C51—C56	174.5 (3)
C2—C3—C4—N11	−114.1 (2)	C50—C51—C52—C53	−179.8 (3)
N12—C6—C7—O12	76.5 (3)	C52—C51—C56—C55	0.4 (5)
N12—C6—C7—C8	−156.8 (2)	C56—C51—C52—C53	−0.1 (4)
N12—C6—C10—N11	0.6 (3)	C51—C52—C53—C54	0.4 (6)
N12—C6—C10—N14	−174.7 (3)	C52—C53—C54—C55	−0.9 (6)
C7—C6—C10—N11	−174.6 (3)	C52—C53—C54—C57	−179.7 (4)
C7—C6—C10—N14	10.1 (6)	C53—C54—C55—C56	1.1 (6)
C10—C6—C7—O12	−108.8 (3)	C57—C54—C55—C56	180.0 (2)
C10—C6—C7—C8	17.9 (4)	C54—C55—C56—C51	−0.9 (5)
O12—C7—C8—N13	68.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H121···O34^i	0.91	1.98	2.889 (3)	173
O32—H321···O16	0.91	2.23	3.013 (3)	144
N13—H130···N12^i	0.86	2.22	2.975 (3)	146
N33—H330···N32^ii	0.86	2.33	2.954 (3)	130

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