Crystal structure of a tripeptide biphenyl hybrid C₅₀H₅₆N₆O₁₀·0.5H₂O

A peptide biphenyl hybrid compound {systematic name: dimethyl 2,2′-[((2S,2′S)-2,2′-{[(2S,2′S)-1,1′-([1,1′-biphen­yl]-2,2′-dicarbon­yl)bis­(pyrrolidine-1,2-diyl-2-carbon­yl)]bis­(aza­nedi­yl)}bis­(3-phenyl­propano­yl))bis­(aza­nedi­yl)](2S,2′S)-dipropionate hemihydrate}, C₅₀H₅₆N₆O₁₀·0.5H₂O, was prepared by coupling of [1,1′-biphen­yl]-2,2′-dicarbonyl dichloride, tri­ethyl­amine and the tripeptide Pro–Phe–Ala in CH₂Cl₂ at 273 K under an N₂ atmosphere. In the crystal, the asymmetric unit contains the peptide biphenyl hybrid accompanied by one-half of a water mol­ecule. A C atom of one of the proline rings is disordered between two positions in a 0.746 (11):0.254 (11) ratio. An important structural aspect of peptide compounds is their capacity to self-associate mediated by inter­molecular and intra­molecular hydrogen bonding. This characteristic can be useful in understanding the inter­actions between peptides and biomacromolecular targets, as well as to explain peptide properties.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.130
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT035_ALERT_1_B _chemical_absolute_configuration Info  Not Given     Please Do !
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       6.27 Report
PLAT097_ALERT_2_B Large Reported Max.  (Positive) Residual Density       1.05 eA-3
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         13 Note
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1 Check
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          4 Check

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00463 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A      ..O2       .       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C      ..O7       .       2.63 Ang.

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          5 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O11        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11B       Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         2% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       1.50 Check
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C6          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C36         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C38         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C47         (Chiral SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         39 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         17 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Dimethyl 2,2'-[((2S,2'S)-2,2'-{[(2S,2'S)-1,1'-([1,1'-biphenyl]-2,2'-dicarbonyl)bis(pyrrolidine-1,2-diyl-2-carbonyl)]bis(azanediyl)}bis(3-phenylpropanoyl))bis(azanediyl)](2S,2'S)-dipropionate hemihydrate

Crystal data

C50H56N6O10·0.5H2O	Dx = 1.226 Mg m^−3
Mr = 910.01	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9965 reflections
a = 9.9955 (5) Å	θ = 3.1–26.5°
b = 15.8364 (7) Å	µ = 0.09 mm^−1
c = 31.1356 (14) Å	T = 100 K
V = 4928.5 (4) Å^3	Prism, clear light yellow
Z = 4	0.28 × 0.2 × 0.15 mm
F(000) = 1932

Data collection

Bruker D8 Quest CMOS diffractometer	8909 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 26.8°, θmin = 2.9°
Tmin = 0.695, Tmax = 0.745	h = −12→12
43863 measured reflections	k = −20→20
10447 independent reflections	l = −39→32

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0688P)^2 + 1.586P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 1.05 e Å^−3
10447 reflections	Δρmin = −0.17 e Å^−3
621 parameters	Absolute structure: Flack x determined using 3422 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
39 restraints	Absolute structure parameter: 0.1 (3)
Primary atom site location: iterative

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O8	0.5783 (2)	0.35379 (15)	0.61299 (7)	0.0290 (5)
O5	0.1677 (2)	0.52485 (14)	0.62202 (7)	0.0300 (5)
O6	0.1527 (2)	0.33804 (15)	0.71036 (7)	0.0297 (5)
O7	0.1823 (2)	0.20517 (14)	0.61792 (8)	0.0328 (5)
O9	0.7545 (2)	0.24915 (17)	0.69600 (8)	0.0368 (6)
O4	0.3271 (2)	0.67992 (16)	0.56633 (8)	0.0358 (6)
O10	0.5908 (3)	0.18598 (15)	0.65811 (8)	0.0376 (6)
O3	0.3607 (2)	0.78162 (16)	0.46470 (8)	0.0366 (6)
O2	0.0132 (3)	0.94017 (16)	0.53066 (9)	0.0458 (7)
N5	0.2180 (2)	0.34595 (17)	0.61273 (8)	0.0211 (5)
H5	0.1869	0.3968	0.6182	0.025*
O1	0.1553 (3)	1.04279 (16)	0.51105 (9)	0.0452 (7)
N2	0.1356 (3)	0.66860 (16)	0.52816 (8)	0.0251 (6)
H2	0.0490	0.6587	0.5292	0.030*
N6	0.4311 (3)	0.32243 (18)	0.66559 (8)	0.0259 (6)
H6	0.3466	0.3178	0.6731	0.031*
N3	0.1878 (3)	0.65960 (17)	0.64292 (8)	0.0296 (6)
N4	−0.0114 (2)	0.37316 (16)	0.66369 (8)	0.0229 (5)
N1	0.1567 (3)	0.82474 (17)	0.48518 (10)	0.0336 (7)
H1	0.0797	0.8092	0.4964	0.040*
C5	0.2483 (3)	0.7659 (2)	0.47812 (10)	0.0255 (7)
C2	0.1053 (4)	0.9653 (2)	0.50913 (12)	0.0329 (8)
C49	0.6401 (3)	0.2466 (2)	0.68322 (10)	0.0273 (7)
C37	0.1444 (3)	0.27814 (19)	0.62330 (10)	0.0234 (6)
C19	0.2126 (3)	0.5774 (2)	0.64748 (10)	0.0236 (6)
C46	0.4634 (3)	0.34112 (19)	0.62472 (10)	0.0226 (6)
C40	0.2546 (3)	0.3822 (2)	0.52165 (9)	0.0246 (6)
C38	0.3471 (3)	0.3369 (2)	0.59253 (9)	0.0226 (6)
H38	0.3491	0.2788	0.5800	0.027*
C32	0.0613 (3)	0.3867 (2)	0.69939 (10)	0.0247 (7)
C25	0.2567 (3)	0.52550 (19)	0.72356 (9)	0.0227 (6)
C20	0.3034 (3)	0.55266 (19)	0.68390 (9)	0.0231 (6)
C33	−0.1105 (3)	0.4298 (2)	0.64412 (10)	0.0272 (7)
H33A	−0.0832	0.4896	0.6468	0.033*
H33B	−0.1999	0.4223	0.6573	0.033*
C45	0.1501 (3)	0.4389 (2)	0.51655 (10)	0.0284 (7)
H45	0.1490	0.4896	0.5328	0.034*
C22	0.5320 (3)	0.5374 (2)	0.70738 (12)	0.0320 (7)
H22	0.6253	0.5417	0.7020	0.038*
C31	0.0216 (3)	0.4610 (2)	0.72602 (10)	0.0268 (7)
C34	−0.1097 (3)	0.4010 (2)	0.59730 (10)	0.0306 (7)
H34A	−0.1946	0.4158	0.5827	0.037*
H34B	−0.0341	0.4263	0.5813	0.037*
C39	0.3631 (3)	0.3978 (2)	0.55481 (9)	0.0254 (7)
H39A	0.3574	0.4567	0.5653	0.031*
H39B	0.4521	0.3897	0.5415	0.031*
C41	0.2561 (3)	0.3086 (2)	0.49701 (10)	0.0292 (7)
H41	0.3279	0.2698	0.5000	0.035*
C23	0.4861 (3)	0.5099 (2)	0.74670 (12)	0.0328 (8)
H23	0.5481	0.4948	0.7685	0.039*
C43	0.0489 (4)	0.3485 (2)	0.46349 (11)	0.0332 (8)
H43	−0.0213	0.3372	0.4437	0.040*
C8	0.1648 (4)	0.6529 (2)	0.40682 (10)	0.0312 (7)
C14	0.2050 (3)	0.6776 (2)	0.56506 (10)	0.0265 (7)
C44	0.0472 (4)	0.4222 (2)	0.48784 (11)	0.0316 (8)
H44	−0.0245	0.4612	0.4848	0.038*
C26	0.1115 (3)	0.5259 (2)	0.73614 (9)	0.0255 (7)
C7	0.1065 (3)	0.6452 (2)	0.45158 (10)	0.0306 (7)
H7A	0.0829	0.5854	0.4570	0.037*
H7B	0.0232	0.6788	0.4531	0.037*
C47	0.5353 (3)	0.3100 (2)	0.69728 (10)	0.0269 (7)
H47	0.5805	0.3654	0.7025	0.032*
C6	0.2021 (3)	0.6751 (2)	0.48676 (10)	0.0265 (7)
H6A	0.2823	0.6374	0.4869	0.032*
C42	0.1532 (4)	0.2917 (2)	0.46815 (10)	0.0326 (8)
H42	0.1546	0.2412	0.4517	0.039*
C21	0.4407 (3)	0.5586 (2)	0.67586 (11)	0.0286 (7)
H21	0.4714	0.5773	0.6486	0.034*
C30	−0.1064 (4)	0.4624 (3)	0.74307 (11)	0.0395 (9)
H30	−0.1668	0.4179	0.7366	0.047*
C36	0.0037 (3)	0.2945 (2)	0.63950 (10)	0.0252 (7)
H36	−0.0263	0.2459	0.6576	0.030*
C24	0.3505 (3)	0.5042 (2)	0.75457 (10)	0.0293 (7)
H24	0.3207	0.4852	0.7819	0.035*
C9	0.1242 (4)	0.7179 (2)	0.37993 (11)	0.0383 (8)
H9	0.0580	0.7568	0.3893	0.046*
C35	−0.0937 (3)	0.3060 (2)	0.60144 (11)	0.0307 (7)
H35A	−0.0560	0.2815	0.5748	0.037*
H35B	−0.1808	0.2787	0.6075	0.037*
C4	0.1237 (4)	0.9350 (2)	0.43102 (12)	0.0353 (8)
H4A	0.1771	0.9056	0.4092	0.053*
H4B	0.1296	0.9961	0.4264	0.053*
H4C	0.0302	0.9170	0.4288	0.053*
C29	−0.1478 (4)	0.5278 (3)	0.76945 (13)	0.0531 (12)
H29	−0.2350	0.5271	0.7816	0.064*
C15	0.1186 (4)	0.6907 (2)	0.60477 (10)	0.0317 (8)
H15	0.0294	0.6629	0.6014	0.038*
C27	0.0672 (3)	0.5929 (3)	0.76131 (12)	0.0390 (9)
H27	0.1256	0.6387	0.7672	0.047*
C13	0.2600 (4)	0.5956 (2)	0.39230 (11)	0.0355 (8)
H13	0.2886	0.5510	0.4105	0.043*
C3	0.1767 (3)	0.9136 (2)	0.47531 (12)	0.0334 (8)
H3	0.2745	0.9266	0.4764	0.040*
C12	0.3135 (4)	0.6032 (3)	0.35134 (12)	0.0440 (9)
H12	0.3776	0.5634	0.3414	0.053*
C10	0.1802 (5)	0.7262 (3)	0.33924 (12)	0.0451 (10)
H10	0.1539	0.7717	0.3212	0.054*
C28	−0.0625 (4)	0.5933 (3)	0.77791 (14)	0.0561 (13)
H28	−0.0917	0.6393	0.7951	0.067*
C11	0.2732 (4)	0.6690 (3)	0.32496 (12)	0.0465 (10)
H11	0.3100	0.6745	0.2970	0.056*
C18	0.2329 (4)	0.7290 (2)	0.67105 (12)	0.0388 (9)
H18C	0.3232	0.7490	0.6628	0.047*	0.746 (11)
H18D	0.2340	0.7114	0.7016	0.047*	0.746 (11)
H18A	0.3292	0.7245	0.6782	0.047*	0.254 (11)
H18B	0.1798	0.7323	0.6978	0.047*	0.254 (11)
C48	0.4734 (4)	0.2800 (3)	0.73931 (11)	0.0402 (9)
H48A	0.4047	0.3202	0.7485	0.060*
H48B	0.5430	0.2761	0.7614	0.060*
H48C	0.4326	0.2243	0.7351	0.060*
C50	0.6830 (5)	0.1212 (2)	0.64429 (13)	0.0473 (10)
H50A	0.7417	0.1438	0.6219	0.071*
H50B	0.6327	0.0730	0.6328	0.071*
H50C	0.7372	0.1026	0.6688	0.071*
C16	0.1028 (5)	0.7859 (3)	0.61383 (13)	0.0511 (11)
H16C	0.0117	0.8053	0.6062	0.061*	0.746 (11)
H16D	0.1688	0.8190	0.5971	0.061*	0.746 (11)
H16A	0.1091	0.8189	0.5869	0.061*	0.254 (11)
H16B	0.0156	0.7978	0.6276	0.061*	0.254 (11)
C1	0.0909 (6)	1.0984 (3)	0.54255 (14)	0.0606 (13)
H1A	−0.0051	1.1017	0.5365	0.091*
H1B	0.1303	1.1549	0.5407	0.091*
H1C	0.1046	1.0756	0.5715	0.091*
O11	0.3543 (5)	0.0810 (3)	0.6507 (2)	0.0484 (14)	0.5
H11A	0.3164	0.1111	0.6307	0.073*	0.5
H11B	0.4078	0.1161	0.6636	0.073*	0.5
C17B	0.1282 (8)	0.7962 (4)	0.6631 (2)	0.0526 (18)	0.746 (11)
H17A	0.1625	0.8533	0.6700	0.063*	0.746 (11)
H17B	0.0459	0.7854	0.6799	0.063*	0.746 (11)
C17A	0.204 (2)	0.8050 (9)	0.6403 (5)	0.047 (3)	0.254 (11)
H17C	0.1801	0.8555	0.6574	0.057*	0.254 (11)
H17D	0.2847	0.8182	0.6233	0.057*	0.254 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O8	0.0180 (11)	0.0412 (13)	0.0278 (12)	0.0043 (9)	0.0010 (9)	−0.0014 (10)
O5	0.0355 (13)	0.0288 (11)	0.0256 (11)	−0.0027 (10)	−0.0080 (10)	0.0001 (10)
O6	0.0248 (11)	0.0390 (12)	0.0254 (11)	0.0010 (10)	−0.0052 (9)	0.0020 (10)
O7	0.0321 (12)	0.0245 (12)	0.0419 (14)	0.0017 (10)	0.0016 (11)	−0.0055 (10)
O9	0.0242 (12)	0.0512 (15)	0.0351 (13)	0.0127 (11)	−0.0037 (10)	0.0015 (11)
O4	0.0274 (13)	0.0468 (14)	0.0333 (12)	0.0080 (11)	−0.0101 (10)	−0.0035 (11)
O10	0.0392 (14)	0.0353 (13)	0.0384 (14)	0.0094 (11)	−0.0051 (11)	−0.0034 (11)
O3	0.0253 (12)	0.0438 (14)	0.0407 (13)	−0.0030 (11)	0.0031 (10)	−0.0034 (12)
O2	0.0446 (16)	0.0348 (14)	0.0578 (17)	−0.0044 (12)	0.0116 (14)	−0.0067 (13)
N5	0.0173 (12)	0.0239 (13)	0.0222 (12)	0.0018 (10)	−0.0022 (10)	−0.0012 (10)
O1	0.0634 (18)	0.0328 (13)	0.0393 (14)	−0.0167 (13)	−0.0107 (13)	−0.0015 (12)
N2	0.0224 (13)	0.0277 (13)	0.0252 (13)	0.0021 (11)	−0.0046 (11)	0.0002 (11)
N6	0.0172 (12)	0.0391 (15)	0.0213 (12)	0.0049 (11)	−0.0014 (10)	0.0013 (12)
N3	0.0371 (15)	0.0299 (14)	0.0218 (13)	0.0084 (12)	−0.0079 (12)	−0.0024 (12)
N4	0.0197 (13)	0.0271 (14)	0.0220 (12)	−0.0007 (10)	−0.0024 (10)	−0.0025 (11)
N1	0.0206 (13)	0.0251 (14)	0.0550 (18)	−0.0025 (11)	0.0028 (13)	0.0033 (14)
C5	0.0217 (15)	0.0329 (17)	0.0219 (14)	−0.0012 (13)	−0.0060 (12)	−0.0029 (13)
C2	0.0330 (18)	0.0254 (17)	0.0403 (19)	−0.0030 (15)	−0.0114 (16)	0.0037 (15)
C49	0.0243 (16)	0.0335 (17)	0.0242 (15)	0.0084 (13)	−0.0011 (13)	0.0054 (14)
C37	0.0239 (15)	0.0243 (16)	0.0219 (14)	−0.0009 (12)	−0.0043 (12)	−0.0028 (13)
C19	0.0226 (15)	0.0288 (16)	0.0194 (14)	0.0006 (12)	0.0019 (12)	−0.0003 (13)
C46	0.0190 (15)	0.0261 (16)	0.0228 (15)	0.0057 (12)	0.0002 (12)	−0.0012 (13)
C40	0.0254 (15)	0.0301 (16)	0.0182 (14)	−0.0049 (13)	0.0025 (12)	0.0018 (13)
C38	0.0183 (14)	0.0271 (16)	0.0224 (14)	0.0047 (12)	−0.0007 (12)	−0.0025 (13)
C32	0.0182 (14)	0.0348 (17)	0.0211 (15)	−0.0048 (13)	0.0005 (12)	0.0031 (14)
C25	0.0175 (14)	0.0295 (16)	0.0211 (14)	0.0007 (12)	−0.0011 (12)	−0.0041 (13)
C20	0.0238 (15)	0.0234 (15)	0.0220 (15)	0.0045 (12)	−0.0012 (12)	−0.0034 (13)
C33	0.0184 (14)	0.0346 (17)	0.0284 (16)	0.0043 (13)	−0.0021 (13)	−0.0027 (14)
C45	0.0318 (17)	0.0260 (16)	0.0273 (16)	−0.0054 (13)	−0.0040 (14)	0.0028 (14)
C22	0.0175 (15)	0.0378 (19)	0.0405 (19)	0.0006 (14)	0.0039 (14)	0.0035 (16)
C31	0.0184 (15)	0.0426 (19)	0.0193 (14)	−0.0038 (14)	−0.0020 (12)	−0.0056 (14)
C34	0.0210 (15)	0.046 (2)	0.0248 (16)	0.0036 (15)	−0.0076 (13)	0.0003 (15)
C39	0.0227 (15)	0.0329 (17)	0.0207 (14)	−0.0008 (13)	−0.0006 (12)	0.0007 (13)
C41	0.0299 (17)	0.0336 (18)	0.0240 (15)	−0.0007 (14)	0.0034 (14)	−0.0016 (14)
C23	0.0194 (16)	0.045 (2)	0.0335 (18)	0.0016 (14)	−0.0076 (14)	0.0080 (16)
C43	0.0337 (18)	0.043 (2)	0.0233 (16)	−0.0124 (16)	−0.0046 (14)	0.0028 (15)
C8	0.0371 (19)	0.0316 (17)	0.0249 (15)	−0.0057 (15)	−0.0093 (14)	−0.0030 (14)
C14	0.0281 (16)	0.0242 (16)	0.0271 (16)	0.0065 (13)	−0.0074 (13)	0.0013 (13)
C44	0.0310 (17)	0.0341 (18)	0.0298 (17)	−0.0034 (14)	−0.0072 (14)	0.0076 (15)
C26	0.0168 (14)	0.0420 (18)	0.0176 (14)	−0.0009 (13)	−0.0022 (12)	−0.0043 (14)
C7	0.0336 (18)	0.0280 (16)	0.0302 (17)	−0.0032 (14)	−0.0070 (14)	−0.0014 (14)
C47	0.0197 (15)	0.0386 (19)	0.0225 (15)	0.0069 (13)	−0.0028 (12)	0.0011 (14)
C6	0.0278 (16)	0.0278 (16)	0.0240 (15)	0.0054 (13)	−0.0035 (13)	−0.0026 (13)
C42	0.0368 (18)	0.0384 (18)	0.0227 (15)	−0.0092 (15)	0.0032 (14)	−0.0059 (14)
C21	0.0258 (16)	0.0329 (17)	0.0271 (16)	−0.0027 (13)	0.0069 (13)	0.0037 (14)
C30	0.0230 (17)	0.065 (2)	0.0305 (17)	−0.0115 (17)	−0.0001 (14)	−0.0164 (18)
C36	0.0216 (15)	0.0269 (16)	0.0270 (16)	−0.0033 (12)	−0.0037 (13)	−0.0027 (13)
C24	0.0242 (16)	0.0427 (19)	0.0210 (15)	−0.0012 (14)	−0.0001 (13)	0.0050 (14)
C9	0.053 (2)	0.0340 (18)	0.0280 (17)	−0.0026 (17)	−0.0114 (16)	−0.0049 (16)
C35	0.0195 (15)	0.043 (2)	0.0298 (17)	−0.0022 (14)	−0.0056 (13)	−0.0112 (15)
C4	0.0323 (18)	0.0298 (17)	0.044 (2)	−0.0040 (14)	0.0060 (16)	0.0004 (16)
C29	0.0184 (17)	0.096 (3)	0.045 (2)	−0.004 (2)	0.0057 (16)	−0.036 (2)
C15	0.0359 (19)	0.0358 (18)	0.0234 (15)	0.0135 (15)	−0.0040 (14)	0.0006 (14)
C27	0.0215 (16)	0.059 (2)	0.0369 (19)	−0.0037 (16)	−0.0039 (14)	−0.0240 (19)
C13	0.042 (2)	0.0325 (18)	0.0319 (17)	−0.0042 (16)	−0.0101 (16)	−0.0050 (15)
C3	0.0238 (16)	0.0261 (16)	0.050 (2)	−0.0059 (13)	−0.0012 (15)	0.0029 (16)
C12	0.039 (2)	0.056 (2)	0.037 (2)	−0.0027 (18)	−0.0057 (16)	−0.0170 (19)
C10	0.064 (3)	0.044 (2)	0.0269 (17)	−0.008 (2)	−0.0122 (18)	0.0006 (17)
C28	0.0237 (18)	0.091 (3)	0.054 (2)	0.000 (2)	0.0028 (17)	−0.046 (3)
C11	0.053 (2)	0.063 (3)	0.0238 (17)	−0.017 (2)	−0.0078 (17)	−0.0028 (18)
C18	0.050 (2)	0.0321 (18)	0.0340 (18)	0.0109 (16)	−0.0127 (17)	−0.0093 (15)
C48	0.0300 (18)	0.066 (3)	0.0249 (17)	0.0155 (18)	−0.0011 (14)	0.0071 (18)
C50	0.068 (3)	0.0342 (19)	0.039 (2)	0.0199 (19)	−0.003 (2)	0.0003 (17)
C16	0.074 (3)	0.043 (2)	0.036 (2)	0.033 (2)	−0.003 (2)	−0.0010 (18)
C1	0.113 (4)	0.032 (2)	0.037 (2)	−0.014 (2)	−0.006 (2)	−0.0101 (18)
O11	0.023 (2)	0.048 (3)	0.074 (4)	0.004 (2)	−0.008 (3)	−0.001 (3)
C17B	0.077 (4)	0.044 (3)	0.037 (3)	0.028 (3)	−0.012 (3)	−0.015 (2)
C17A	0.074 (7)	0.029 (6)	0.040 (6)	0.015 (6)	−0.010 (6)	−0.019 (5)

Geometric parameters (Å, º)

O8—C46	1.221 (4)	C8—C9	1.388 (5)
O5—C19	1.234 (4)	C8—C13	1.390 (5)
O6—C32	1.243 (4)	C14—C15	1.523 (5)
O7—C37	1.227 (4)	C44—H44	0.9500
O9—C49	1.211 (4)	C26—C27	1.391 (5)
O4—C14	1.221 (4)	C7—H7A	0.9900
O10—C49	1.333 (4)	C7—H7B	0.9900
O10—C50	1.445 (4)	C7—C6	1.529 (4)
O3—C5	1.224 (4)	C47—H47	1.0000
O2—C2	1.207 (4)	C47—C48	1.523 (5)
N5—H5	0.8800	C6—H6A	1.0000
N5—C37	1.343 (4)	C42—H42	0.9500
N5—C38	1.443 (4)	C21—H21	0.9500
O1—C2	1.326 (4)	C30—H30	0.9500
O1—C1	1.466 (5)	C30—C29	1.384 (6)
N2—H2	0.8800	C36—H36	1.0000
N2—C14	1.350 (4)	C36—C35	1.544 (4)
N2—C6	1.454 (4)	C24—H24	0.9500
N6—H6	0.8800	C9—H9	0.9500
N6—C46	1.346 (4)	C9—C10	1.391 (5)
N6—C47	1.448 (4)	C35—H35A	0.9900
N3—C19	1.332 (4)	C35—H35B	0.9900
N3—C15	1.460 (4)	C4—H4A	0.9800
N3—C18	1.476 (4)	C4—H4B	0.9800
N4—C32	1.345 (4)	C4—H4C	0.9800
N4—C33	1.469 (4)	C4—C3	1.515 (5)
N4—C36	1.463 (4)	C29—H29	0.9500
N1—H1	0.8800	C29—C28	1.369 (6)
N1—C5	1.325 (4)	C15—H15	1.0000
N1—C3	1.454 (4)	C15—C16	1.542 (5)
C5—C6	1.534 (5)	C27—H27	0.9500
C2—C3	1.513 (5)	C27—C28	1.395 (5)
C49—C47	1.515 (4)	C13—H13	0.9500
C37—C36	1.516 (4)	C13—C12	1.388 (5)
C19—C20	1.505 (4)	C3—H3	1.0000
C46—C38	1.536 (4)	C12—H12	0.9500
C40—C45	1.386 (5)	C12—C11	1.387 (6)
C40—C39	1.518 (4)	C10—H10	0.9500
C40—C41	1.396 (5)	C10—C11	1.372 (6)
C38—H38	1.0000	C28—H28	0.9500
C38—C39	1.528 (4)	C11—H11	0.9500
C32—C31	1.492 (5)	C18—H18C	0.9900
C25—C20	1.388 (4)	C18—H18D	0.9900
C25—C26	1.503 (4)	C18—H18A	0.9900
C25—C24	1.387 (4)	C18—H18B	0.9900
C20—C21	1.398 (5)	C18—C17B	1.513 (6)
C33—H33A	0.9900	C18—C17A	1.566 (15)
C33—H33B	0.9900	C48—H48A	0.9800
C33—C34	1.527 (4)	C48—H48B	0.9800
C45—H45	0.9500	C48—H48C	0.9800
C45—C44	1.388 (5)	C50—H50A	0.9800
C22—H22	0.9500	C50—H50B	0.9800
C22—C23	1.378 (5)	C50—H50C	0.9800
C22—C21	1.382 (5)	C16—H16C	0.9900
C31—C26	1.402 (5)	C16—H16D	0.9900
C31—C30	1.385 (5)	C16—H16A	0.9900
C34—H34A	0.9900	C16—H16B	0.9900
C34—H34B	0.9900	C16—C17B	1.563 (7)
C34—C35	1.519 (5)	C16—C17A	1.335 (17)
C39—H39A	0.9900	C1—H1A	0.9800
C39—H39B	0.9900	C1—H1B	0.9800
C41—H41	0.9500	C1—H1C	0.9800
C41—C42	1.391 (5)	O11—H11A	0.8701
C23—H23	0.9500	O11—H11B	0.8694
C23—C24	1.380 (5)	C17B—H17A	0.9900
C43—H43	0.9500	C17B—H17B	0.9900
C43—C44	1.392 (5)	C17A—H17C	0.9900
C43—C42	1.386 (5)	C17A—H17D	0.9900
C8—C7	1.515 (5)
C49—O10—C50	116.8 (3)	C41—C42—H42	120.0
C37—N5—H5	119.4	C43—C42—C41	119.9 (3)
C37—N5—C38	121.2 (3)	C43—C42—H42	120.0
C38—N5—H5	119.4	C20—C21—H21	119.8
C2—O1—C1	114.9 (3)	C22—C21—C20	120.3 (3)
C14—N2—H2	119.6	C22—C21—H21	119.8
C14—N2—C6	120.8 (3)	C31—C30—H30	119.5
C6—N2—H2	119.6	C29—C30—C31	121.1 (4)
C46—N6—H6	119.9	C29—C30—H30	119.5
C46—N6—C47	120.1 (3)	N4—C36—C37	114.4 (2)
C47—N6—H6	119.9	N4—C36—H36	109.5
C19—N3—C15	120.3 (3)	N4—C36—C35	103.3 (2)
C19—N3—C18	127.4 (3)	C37—C36—H36	109.5
C15—N3—C18	112.1 (3)	C37—C36—C35	110.5 (3)
C32—N4—C33	127.6 (3)	C35—C36—H36	109.5
C32—N4—C36	120.4 (3)	C25—C24—H24	119.2
C36—N4—C33	112.1 (2)	C23—C24—C25	121.6 (3)
C5—N1—H1	118.3	C23—C24—H24	119.2
C5—N1—C3	123.4 (3)	C8—C9—H9	120.0
C3—N1—H1	118.3	C8—C9—C10	120.1 (4)
O3—C5—N1	123.2 (3)	C10—C9—H9	120.0
O3—C5—C6	121.8 (3)	C34—C35—C36	104.4 (3)
N1—C5—C6	115.0 (3)	C34—C35—H35A	110.9
O2—C2—O1	124.6 (4)	C34—C35—H35B	110.9
O2—C2—C3	124.6 (3)	C36—C35—H35A	110.9
O1—C2—C3	110.8 (3)	C36—C35—H35B	110.9
O9—C49—O10	124.4 (3)	H35A—C35—H35B	108.9
O9—C49—C47	122.4 (3)	H4A—C4—H4B	109.5
O10—C49—C47	113.0 (3)	H4A—C4—H4C	109.5
O7—C37—N5	123.4 (3)	H4B—C4—H4C	109.5
O7—C37—C36	119.5 (3)	C3—C4—H4A	109.5
N5—C37—C36	116.9 (3)	C3—C4—H4B	109.5
O5—C19—N3	121.5 (3)	C3—C4—H4C	109.5
O5—C19—C20	121.9 (3)	C30—C29—H29	120.2
N3—C19—C20	116.6 (3)	C28—C29—C30	119.6 (4)
O8—C46—N6	123.0 (3)	C28—C29—H29	120.2
O8—C46—C38	121.6 (3)	N3—C15—C14	110.2 (3)
N6—C46—C38	115.2 (3)	N3—C15—H15	111.1
C45—C40—C39	120.8 (3)	N3—C15—C16	103.3 (3)
C45—C40—C41	119.1 (3)	C14—C15—H15	111.1
C41—C40—C39	120.1 (3)	C14—C15—C16	109.9 (3)
N5—C38—C46	112.8 (2)	C16—C15—H15	111.1
N5—C38—H38	106.2	C26—C27—H27	119.7
N5—C38—C39	111.5 (2)	C26—C27—C28	120.6 (4)
C46—C38—H38	106.2	C28—C27—H27	119.7
C39—C38—C46	113.3 (3)	C8—C13—H13	119.8
C39—C38—H38	106.2	C12—C13—C8	120.4 (4)
O6—C32—N4	121.7 (3)	C12—C13—H13	119.8
O6—C32—C31	122.1 (3)	N1—C3—C2	108.2 (3)
N4—C32—C31	116.2 (3)	N1—C3—C4	111.1 (3)
C20—C25—C26	123.7 (3)	N1—C3—H3	109.0
C24—C25—C20	117.9 (3)	C2—C3—C4	110.4 (3)
C24—C25—C26	118.2 (3)	C2—C3—H3	109.0
C25—C20—C19	123.3 (3)	C4—C3—H3	109.0
C25—C20—C21	120.7 (3)	C13—C12—H12	120.1
C21—C20—C19	116.1 (3)	C11—C12—C13	119.8 (4)
N4—C33—H33A	111.3	C11—C12—H12	120.1
N4—C33—H33B	111.3	C9—C10—H10	119.8
N4—C33—C34	102.2 (2)	C11—C10—C9	120.4 (4)
H33A—C33—H33B	109.2	C11—C10—H10	119.8
C34—C33—H33A	111.3	C29—C28—C27	120.2 (4)
C34—C33—H33B	111.3	C29—C28—H28	119.9
C40—C45—H45	119.7	C27—C28—H28	119.9
C40—C45—C44	120.6 (3)	C12—C11—H11	120.0
C44—C45—H45	119.7	C10—C11—C12	120.1 (4)
C23—C22—H22	120.4	C10—C11—H11	120.0
C23—C22—C21	119.2 (3)	N3—C18—H18C	111.3
C21—C22—H22	120.4	N3—C18—H18D	111.3
C26—C31—C32	122.2 (3)	N3—C18—H18A	112.0
C30—C31—C32	118.1 (3)	N3—C18—H18B	112.0
C30—C31—C26	119.6 (3)	N3—C18—C17B	102.4 (3)
C33—C34—H34A	111.3	N3—C18—C17A	98.7 (6)
C33—C34—H34B	111.3	H18C—C18—H18D	109.2
H34A—C34—H34B	109.2	H18A—C18—H18B	109.7
C35—C34—C33	102.4 (3)	C17B—C18—H18C	111.3
C35—C34—H34A	111.3	C17B—C18—H18D	111.3
C35—C34—H34B	111.3	C17A—C18—H18A	112.0
C40—C39—C38	110.2 (3)	C17A—C18—H18B	112.0
C40—C39—H39A	109.6	C47—C48—H48A	109.5
C40—C39—H39B	109.6	C47—C48—H48B	109.5
C38—C39—H39A	109.6	C47—C48—H48C	109.5
C38—C39—H39B	109.6	H48A—C48—H48B	109.5
H39A—C39—H39B	108.1	H48A—C48—H48C	109.5
C40—C41—H41	119.7	H48B—C48—H48C	109.5
C42—C41—C40	120.5 (3)	O10—C50—H50A	109.5
C42—C41—H41	119.7	O10—C50—H50B	109.5
C22—C23—H23	119.8	O10—C50—H50C	109.5
C22—C23—C24	120.4 (3)	H50A—C50—H50B	109.5
C24—C23—H23	119.8	H50A—C50—H50C	109.5
C44—C43—H43	120.1	H50B—C50—H50C	109.5
C42—C43—H43	120.1	C15—C16—H16C	110.7
C42—C43—C44	119.8 (3)	C15—C16—H16D	110.7
C9—C8—C7	120.1 (3)	C15—C16—H16A	110.8
C9—C8—C13	119.2 (3)	C15—C16—H16B	110.8
C13—C8—C7	120.6 (3)	C15—C16—C17B	105.4 (3)
O4—C14—N2	123.0 (3)	H16C—C16—H16D	108.8
O4—C14—C15	122.5 (3)	H16A—C16—H16B	108.8
N2—C14—C15	114.4 (3)	C17B—C16—H16C	110.7
C45—C44—C43	120.1 (3)	C17B—C16—H16D	110.7
C45—C44—H44	120.0	C17A—C16—C15	104.9 (6)
C43—C44—H44	120.0	C17A—C16—H16A	110.8
C31—C26—C25	123.9 (3)	C17A—C16—H16B	110.8
C27—C26—C25	117.3 (3)	O1—C1—H1A	109.5
C27—C26—C31	118.8 (3)	O1—C1—H1B	109.5
C8—C7—H7A	108.9	O1—C1—H1C	109.5
C8—C7—H7B	108.9	H1A—C1—H1B	109.5
C8—C7—C6	113.2 (3)	H1A—C1—H1C	109.5
H7A—C7—H7B	107.8	H1B—C1—H1C	109.5
C6—C7—H7A	108.9	H11A—O11—H11B	104.4
C6—C7—H7B	108.9	C18—C17B—C16	101.5 (4)
N6—C47—C49	113.0 (3)	C18—C17B—H17A	111.5
N6—C47—H47	108.4	C18—C17B—H17B	111.5
N6—C47—C48	109.6 (3)	C16—C17B—H17A	111.5
C49—C47—H47	108.4	C16—C17B—H17B	111.5
C49—C47—C48	108.9 (3)	H17A—C17B—H17B	109.3
C48—C47—H47	108.4	C18—C17A—H17C	109.6
N2—C6—C5	111.1 (3)	C18—C17A—H17D	109.6
N2—C6—C7	109.1 (3)	C16—C17A—C18	110.2 (11)
N2—C6—H6A	108.6	C16—C17A—H17C	109.6
C5—C6—H6A	108.6	C16—C17A—H17D	109.6
C7—C6—C5	110.7 (3)	H17C—C17A—H17D	108.1
C7—C6—H6A	108.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11B···O10	0.87	2.15	2.899 (6)	145
O11—H11A···O7	0.87	2.03	2.804 (6)	145
C29—H29···O11^i	0.95	2.57	3.339 (7)	138
N5—H5···O5	0.88	2.04	2.892 (3)	163
N2—H2···O3^ii	0.88	2.11	2.867 (4)	143
C6—H6A···O2^iii	1.00	2.67	3.647 (4)	165
C4—H4C···O4^ii	0.98	2.55	3.480 (4)	159
C27—H27···O9^iv	0.95	2.41	3.327 (5)	162
C1—H1B···O7^v	0.98	2.59	3.033 (5)	108
C1—H1C···O7^v	0.98	2.63	3.033 (5)	105

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