N-[tert-Butoxy­carbonyl­glycyl-(Z)-α,β-dehydro­phenyl­alanylglycyl-(Z)-α,β-dehydro­phenyl­alan­yl]glycine methyl ester

In the crystal structure of the penta­peptide Boc⁰—Gly¹–Δ^ZPhe²—Gly³–Δ^ZPhe⁴—Gly⁵—OMe, C₃₀H₃₅N₅O₈, the values of torsion angles Φ and Ψ show the presence of two type III′ β-turns, at the Δ^ZPhe² and Gly³ residues, and Gly³ and Δ^ZPhe⁴ residues. All amino acids in the peptide are linked trans to each other. Two intra­molecular N—H...O hydrogen bonds, between CO and NH groups, stabilize β-turns present in the peptide.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.102
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.74
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.91 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

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           75.32
           From the CIF: _reflns_number_total               3011
           Count of symmetry unique reflns         3275
           Completeness (_total/calc)             91.94%
           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

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

N-[tert-Butoxycarbonylglycyl-(Z)-α,β-dehydrophenylalanylglycyl- (Z)-α,β-dehydrophenylalanyl]glycine methyl ester

Crystal data

C30H35N5O8	F(000) = 628
Mr = 593.63	Dx = 1.320 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb	Cell parameters from 10292 reflections
a = 10.127 (3) Å	θ = 4–75°
b = 10.036 (3) Å	µ = 0.81 mm^−1
c = 14.700 (4) Å	T = 100 K
β = 90.23 (3)°	Needle, colourless
V = 1494.0 (7) Å^3	0.29 × 0.11 × 0.04 mm
Z = 2

Data collection

Xcalibur PX κ-geometry diffractometer with CCD detector	3011 independent reflections
Radiation source: fine-focus sealed tube	2792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 75.3°, θmin = 4.4°
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2003)	h = −10→12
Tmin = 0.842, Tmax = 0.966	k = −12→8
8750 measured reflections	l = −18→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0714P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.008
3011 reflections	Δρmax = 0.20 e Å^−3
389 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3160 (2)	0.4731 (2)	0.83165 (15)	0.0243 (5)
H1	0.2619	0.4092	0.8485	0.029*
C6	0.3605 (2)	0.4802 (3)	0.73796 (17)	0.0232 (5)
H6A	0.3739	0.5745	0.7206	0.028*
H6B	0.2921	0.4420	0.6973	0.028*
C7	0.4891 (2)	0.4039 (2)	0.72633 (16)	0.0176 (5)
O3	0.49140 (17)	0.28116 (19)	0.73621 (12)	0.0217 (4)
N2	0.5978 (2)	0.4753 (2)	0.70695 (14)	0.0197 (4)
H2	0.5919	0.5625	0.7020	0.024*
C8	0.7224 (2)	0.4120 (3)	0.69428 (18)	0.0203 (5)
C9	0.8326 (2)	0.4444 (3)	0.74036 (18)	0.0222 (5)
H9A	0.9083	0.3944	0.7234	0.027*
C10	0.8570 (3)	0.5426 (3)	0.81195 (18)	0.0235 (5)
C15	0.9886 (3)	0.5753 (3)	0.8302 (2)	0.0330 (6)
H15A	1.0569	0.5309	0.7980	0.040*
C14	1.0215 (3)	0.6709 (4)	0.8942 (2)	0.0388 (7)
H14A	1.1117	0.6928	0.9044	0.047*
C13	0.9244 (3)	0.7347 (3)	0.9431 (2)	0.0359 (7)
H13A	0.9469	0.8003	0.9871	0.043*
C12	0.7936 (3)	0.7019 (3)	0.9272 (2)	0.0309 (6)
H12A	0.7263	0.7448	0.9612	0.037*
C11	0.7589 (3)	0.6074 (3)	0.86241 (19)	0.0263 (6)
H11A	0.6685	0.5867	0.8522	0.032*
C16	0.7291 (2)	0.3071 (2)	0.62268 (17)	0.0199 (5)
O4	0.81400 (18)	0.21824 (18)	0.62395 (14)	0.0247 (4)
N3	0.6370 (2)	0.3148 (2)	0.55606 (14)	0.0206 (4)
H3	0.5829	0.3834	0.5542	0.025*
C17	0.6264 (3)	0.2115 (2)	0.48779 (17)	0.0210 (5)
H17A	0.7131	0.2014	0.4577	0.025*
H17B	0.5620	0.2403	0.4410	0.025*
C18	0.5840 (2)	0.0766 (2)	0.52411 (16)	0.0176 (5)
O5	0.59050 (17)	−0.02280 (19)	0.47482 (12)	0.0222 (4)
N4	0.5418 (2)	0.0722 (2)	0.61116 (14)	0.0180 (4)
H4	0.5220	0.1470	0.6392	0.022*
C19	0.5288 (2)	−0.0505 (2)	0.65850 (16)	0.0181 (5)
C20	0.4247 (2)	−0.0834 (3)	0.71030 (16)	0.0195 (5)
H20A	0.4321	−0.1662	0.7411	0.023*
C21	0.3007 (2)	−0.0103 (3)	0.72645 (17)	0.0206 (5)
C26	0.2345 (3)	−0.0382 (3)	0.80772 (18)	0.0259 (5)
H26A	0.2678	−0.1053	0.8472	0.031*
C25	0.1213 (3)	0.0305 (3)	0.83142 (19)	0.0311 (6)
H25A	0.0788	0.0118	0.8874	0.037*
C24	0.0700 (3)	0.1266 (3)	0.7736 (2)	0.0295 (6)
H24A	−0.0072	0.1745	0.7901	0.035*
C23	0.1318 (3)	0.1525 (3)	0.69133 (19)	0.0275 (6)
H23A	0.0954	0.2167	0.6510	0.033*
C22	0.2469 (3)	0.0849 (3)	0.66746 (18)	0.0234 (5)
H22A	0.2888	0.1034	0.6112	0.028*
C27	0.6482 (2)	−0.1379 (2)	0.66125 (16)	0.0191 (5)
O6	0.63839 (19)	−0.25896 (18)	0.67562 (14)	0.0261 (4)
N5	0.7663 (2)	−0.0786 (2)	0.65227 (14)	0.0204 (4)
H5	0.7711	0.0071	0.6401	0.024*
C28	0.8853 (2)	−0.1562 (3)	0.66268 (17)	0.0218 (5)
H28A	0.8822	−0.2042	0.7215	0.026*
H28B	0.9622	−0.0953	0.6643	0.026*
C29	0.9036 (3)	−0.2561 (3)	0.58649 (18)	0.0226 (5)
O7	0.8448 (2)	−0.2556 (2)	0.51565 (14)	0.0361 (5)
O8	0.99670 (19)	−0.3460 (2)	0.60951 (14)	0.0284 (4)
O2	0.4264 (2)	0.6598 (2)	0.87350 (13)	0.0333 (5)
C5	0.3579 (2)	0.5651 (3)	0.89348 (18)	0.0217 (5)
O1	0.31083 (19)	0.5358 (2)	0.97633 (12)	0.0254 (4)
C1	0.3547 (3)	0.6138 (3)	1.05692 (17)	0.0245 (6)
C3	0.2766 (4)	0.5513 (5)	1.1327 (2)	0.0560 (11)
H3A	0.1822	0.5669	1.1224	0.084*
H3B	0.3031	0.5909	1.1909	0.084*
H3C	0.2936	0.4552	1.1341	0.084*
C2	0.3214 (5)	0.7589 (4)	1.0482 (3)	0.0575 (12)
H2A	0.3722	0.7979	0.9982	0.086*
H2B	0.3434	0.8049	1.1050	0.086*
H2C	0.2268	0.7687	1.0355	0.086*
C4	0.4998 (3)	0.5885 (5)	1.0718 (2)	0.0533 (12)
H4A	0.5501	0.6271	1.0215	0.080*
H4B	0.5158	0.4923	1.0745	0.080*
H4C	0.5278	0.6297	1.1292	0.080*
C30	1.0203 (3)	−0.4494 (3)	0.5428 (2)	0.0335 (7)
H30A	1.0895	−0.5094	0.5652	0.050*
H30B	1.0486	−0.4087	0.4855	0.050*
H30C	0.9388	−0.5000	0.5327	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0244 (10)	0.0276 (11)	0.0209 (10)	0.0016 (9)	0.0043 (8)	−0.0047 (10)
C6	0.0239 (12)	0.0262 (13)	0.0194 (12)	0.0059 (11)	0.0011 (9)	−0.0036 (11)
C7	0.0211 (12)	0.0156 (11)	0.0160 (10)	0.0010 (9)	0.0008 (9)	−0.0015 (9)
O3	0.0263 (9)	0.0170 (8)	0.0219 (8)	−0.0012 (7)	0.0032 (7)	0.0007 (7)
N2	0.0204 (10)	0.0136 (9)	0.0250 (10)	0.0013 (8)	−0.0001 (8)	−0.0002 (9)
C8	0.0221 (12)	0.0174 (11)	0.0213 (11)	−0.0016 (10)	0.0016 (9)	0.0000 (10)
C9	0.0233 (12)	0.0182 (12)	0.0252 (12)	−0.0018 (10)	0.0013 (10)	0.0030 (10)
C10	0.0248 (12)	0.0205 (12)	0.0252 (12)	−0.0028 (10)	−0.0040 (10)	0.0021 (11)
C15	0.0267 (14)	0.0325 (14)	0.0397 (16)	0.0025 (12)	−0.0053 (12)	−0.0028 (13)
C14	0.0315 (15)	0.0415 (17)	0.0432 (17)	−0.0041 (14)	−0.0127 (13)	−0.0075 (15)
C13	0.0432 (17)	0.0315 (15)	0.0328 (15)	−0.0055 (14)	−0.0077 (13)	−0.0043 (13)
C12	0.0385 (15)	0.0277 (14)	0.0265 (13)	−0.0037 (12)	−0.0006 (11)	−0.0044 (12)
C11	0.0291 (13)	0.0264 (13)	0.0234 (12)	−0.0054 (11)	0.0002 (10)	−0.0005 (11)
C16	0.0209 (11)	0.0162 (11)	0.0227 (11)	−0.0013 (9)	0.0023 (9)	0.0012 (10)
O4	0.0238 (8)	0.0181 (8)	0.0320 (10)	0.0026 (7)	0.0002 (8)	−0.0007 (8)
N3	0.0280 (10)	0.0141 (9)	0.0197 (10)	0.0025 (8)	0.0015 (8)	0.0008 (8)
C17	0.0291 (12)	0.0148 (11)	0.0192 (11)	−0.0020 (10)	0.0008 (10)	0.0004 (10)
C18	0.0225 (11)	0.0139 (10)	0.0164 (11)	0.0013 (9)	−0.0021 (8)	0.0007 (9)
O5	0.0288 (9)	0.0200 (8)	0.0177 (8)	−0.0015 (7)	−0.0008 (7)	−0.0034 (8)
N4	0.0255 (10)	0.0099 (8)	0.0185 (10)	0.0000 (8)	0.0036 (8)	0.0008 (8)
C19	0.0248 (11)	0.0129 (10)	0.0167 (10)	−0.0025 (9)	−0.0010 (9)	−0.0003 (9)
C20	0.0268 (12)	0.0157 (10)	0.0159 (10)	−0.0023 (10)	−0.0002 (9)	−0.0004 (10)
C21	0.0230 (11)	0.0194 (12)	0.0192 (11)	−0.0035 (9)	0.0008 (9)	−0.0012 (10)
C26	0.0271 (13)	0.0286 (13)	0.0222 (12)	−0.0003 (11)	0.0016 (10)	0.0057 (11)
C25	0.0271 (13)	0.0416 (17)	0.0245 (12)	−0.0008 (12)	0.0056 (10)	0.0057 (13)
C24	0.0250 (13)	0.0324 (14)	0.0310 (14)	0.0029 (11)	0.0042 (11)	0.0012 (13)
C23	0.0258 (12)	0.0281 (13)	0.0287 (13)	0.0029 (11)	−0.0008 (10)	0.0057 (12)
C22	0.0227 (12)	0.0252 (13)	0.0222 (12)	−0.0011 (10)	0.0014 (10)	0.0052 (11)
C27	0.0264 (12)	0.0140 (11)	0.0168 (10)	0.0004 (10)	0.0021 (9)	0.0008 (9)
O6	0.0323 (9)	0.0144 (8)	0.0317 (10)	−0.0008 (8)	0.0041 (8)	0.0047 (8)
N5	0.0240 (10)	0.0150 (9)	0.0221 (10)	−0.0005 (8)	0.0000 (8)	−0.0003 (9)
C28	0.0259 (12)	0.0185 (11)	0.0211 (11)	0.0042 (10)	0.0007 (9)	−0.0023 (10)
C29	0.0253 (12)	0.0190 (11)	0.0234 (12)	0.0029 (10)	0.0039 (10)	0.0003 (11)
O7	0.0383 (11)	0.0444 (12)	0.0256 (10)	0.0102 (10)	−0.0026 (8)	−0.0111 (10)
O8	0.0335 (10)	0.0222 (9)	0.0295 (9)	0.0097 (8)	0.0041 (8)	−0.0018 (9)
O2	0.0478 (12)	0.0320 (11)	0.0202 (9)	−0.0117 (10)	0.0016 (8)	0.0016 (9)
C5	0.0240 (12)	0.0223 (12)	0.0187 (11)	0.0045 (10)	0.0030 (9)	0.0008 (10)
O1	0.0318 (9)	0.0288 (10)	0.0157 (8)	−0.0029 (8)	0.0036 (7)	−0.0037 (8)
C1	0.0286 (13)	0.0293 (14)	0.0156 (11)	0.0020 (11)	−0.0001 (10)	−0.0031 (11)
C3	0.077 (3)	0.065 (3)	0.0265 (16)	−0.030 (2)	0.0223 (17)	−0.0123 (18)
C2	0.106 (3)	0.0331 (18)	0.0335 (17)	0.023 (2)	−0.022 (2)	−0.0103 (15)
C4	0.0327 (16)	0.100 (4)	0.0267 (15)	0.0134 (19)	−0.0029 (12)	−0.0195 (19)
C30	0.0415 (16)	0.0220 (13)	0.0370 (16)	0.0059 (12)	0.0135 (13)	−0.0046 (13)

Geometric parameters (Å, º)

N1—C5	1.362 (4)	C21—C22	1.399 (4)
N1—C6	1.452 (3)	C21—C26	1.401 (3)
N1—H1	0.8800	C26—C25	1.383 (4)
C6—C7	1.521 (3)	C26—H26A	0.9500
C6—H6A	0.9900	C25—C24	1.386 (4)
C6—H6B	0.9900	C25—H25A	0.9500
C7—O3	1.240 (3)	C24—C23	1.388 (4)
C7—N2	1.345 (3)	C24—H24A	0.9500
N2—C8	1.425 (3)	C23—C22	1.395 (4)
N2—H2	0.8800	C23—H23A	0.9500
C8—C9	1.343 (4)	C22—H22A	0.9500
C8—C16	1.491 (4)	C27—O6	1.237 (3)
C9—C10	1.462 (4)	C27—N5	1.343 (3)
C9—H9A	0.9500	N5—C28	1.442 (3)
C10—C15	1.398 (4)	N5—H5	0.8800
C10—C11	1.402 (4)	C28—C29	1.515 (4)
C15—C14	1.384 (5)	C28—H28A	0.9900
C15—H15A	0.9500	C28—H28B	0.9900
C14—C13	1.378 (5)	C29—O7	1.198 (4)
C14—H14A	0.9500	C29—O8	1.347 (3)
C13—C12	1.385 (4)	O8—C30	1.447 (3)
C13—H13A	0.9500	O2—C5	1.214 (3)
C12—C11	1.387 (4)	C5—O1	1.342 (3)
C12—H12A	0.9500	O1—C1	1.486 (3)
C11—H11A	0.9500	C1—C2	1.500 (4)
C16—O4	1.239 (3)	C1—C4	1.506 (4)
C16—N3	1.352 (3)	C1—C3	1.506 (4)
N3—C17	1.447 (3)	C3—H3A	0.9800
N3—H3	0.8800	C3—H3B	0.9800
C17—C18	1.517 (3)	C3—H3C	0.9800
C17—H17A	0.9900	C2—H2A	0.9800
C17—H17B	0.9900	C2—H2B	0.9800
C18—O5	1.235 (3)	C2—H2C	0.9800
C18—N4	1.351 (3)	C4—H4A	0.9800
N4—C19	1.420 (3)	C4—H4B	0.9800
N4—H4	0.8800	C4—H4C	0.9800
C19—C20	1.344 (3)	C30—H30A	0.9800
C19—C27	1.494 (3)	C30—H30B	0.9800
C20—C21	1.474 (3)	C30—H30C	0.9800
C20—H20A	0.9500
C5—N1—C6	120.2 (2)	C25—C26—C21	121.0 (3)
C5—N1—H1	119.9	C25—C26—H26A	119.5
C6—N1—H1	119.9	C21—C26—H26A	119.5
N1—C6—C7	110.5 (2)	C26—C25—C24	120.1 (3)
N1—C6—H6A	109.5	C26—C25—H25A	120.0
C7—C6—H6A	109.5	C24—C25—H25A	120.0
N1—C6—H6B	109.5	C25—C24—C23	119.7 (3)
C7—C6—H6B	109.5	C25—C24—H24A	120.2
H6A—C6—H6B	108.1	C23—C24—H24A	120.2
O3—C7—N2	122.6 (2)	C24—C23—C22	120.5 (3)
O3—C7—C6	120.1 (2)	C24—C23—H23A	119.7
N2—C7—C6	117.2 (2)	C22—C23—H23A	119.7
C7—N2—C8	121.1 (2)	C23—C22—C21	120.0 (2)
C7—N2—H2	119.5	C23—C22—H22A	120.0
C8—N2—H2	119.5	C21—C22—H22A	120.0
C9—C8—N2	124.1 (2)	O6—C27—N5	121.6 (2)
C9—C8—C16	119.1 (2)	O6—C27—C19	121.1 (2)
N2—C8—C16	116.7 (2)	N5—C27—C19	117.3 (2)
C8—C9—C10	131.6 (3)	C27—N5—C28	119.7 (2)
C8—C9—H9A	114.2	C27—N5—H5	120.2
C10—C9—H9A	114.2	C28—N5—H5	120.2
C15—C10—C11	117.8 (3)	N5—C28—C29	112.6 (2)
C15—C10—C9	117.1 (3)	N5—C28—H28A	109.1
C11—C10—C9	125.1 (2)	C29—C28—H28A	109.1
C14—C15—C10	121.4 (3)	N5—C28—H28B	109.1
C14—C15—H15A	119.3	C29—C28—H28B	109.1
C10—C15—H15A	119.3	H28A—C28—H28B	107.8
C13—C14—C15	120.4 (3)	O7—C29—O8	124.5 (3)
C13—C14—H14A	119.8	O7—C29—C28	125.3 (2)
C15—C14—H14A	119.8	O8—C29—C28	110.2 (2)
C14—C13—C12	119.1 (3)	C29—O8—C30	115.3 (2)
C14—C13—H13A	120.5	O2—C5—O1	126.6 (3)
C12—C13—H13A	120.5	O2—C5—N1	123.1 (2)
C13—C12—C11	121.2 (3)	O1—C5—N1	110.2 (2)
C13—C12—H12A	119.4	C5—O1—C1	120.1 (2)
C11—C12—H12A	119.4	O1—C1—C2	112.1 (2)
C12—C11—C10	120.1 (3)	O1—C1—C4	108.4 (2)
C12—C11—H11A	119.9	C2—C1—C4	113.3 (4)
C10—C11—H11A	119.9	O1—C1—C3	102.4 (2)
O4—C16—N3	121.9 (2)	C2—C1—C3	110.5 (3)
O4—C16—C8	122.1 (2)	C4—C1—C3	109.7 (3)
N3—C16—C8	116.0 (2)	C1—C3—H3A	109.5
C16—N3—C17	120.7 (2)	C1—C3—H3B	109.5
C16—N3—H3	119.7	H3A—C3—H3B	109.5
C17—N3—H3	119.7	C1—C3—H3C	109.5
N3—C17—C18	114.6 (2)	H3A—C3—H3C	109.5
N3—C17—H17A	108.6	H3B—C3—H3C	109.5
C18—C17—H17A	108.6	C1—C2—H2A	109.5
N3—C17—H17B	108.6	C1—C2—H2B	109.5
C18—C17—H17B	108.6	H2A—C2—H2B	109.5
H17A—C17—H17B	107.6	C1—C2—H2C	109.5
O5—C18—N4	123.1 (2)	H2A—C2—H2C	109.5
O5—C18—C17	119.9 (2)	H2B—C2—H2C	109.5
N4—C18—C17	117.0 (2)	C1—C4—H4A	109.5
C18—N4—C19	121.5 (2)	C1—C4—H4B	109.5
C18—N4—H4	119.2	H4A—C4—H4B	109.5
C19—N4—H4	119.2	C1—C4—H4C	109.5
C20—C19—N4	124.4 (2)	H4A—C4—H4C	109.5
C20—C19—C27	118.5 (2)	H4B—C4—H4C	109.5
N4—C19—C27	116.4 (2)	O8—C30—H30A	109.5
C19—C20—C21	129.7 (2)	O8—C30—H30B	109.5
C19—C20—H20A	115.1	H30A—C30—H30B	109.5
C21—C20—H20A	115.1	O8—C30—H30C	109.5
C22—C21—C26	118.6 (2)	H30A—C30—H30C	109.5
C22—C21—C20	124.7 (2)	H30B—C30—H30C	109.5
C26—C21—C20	116.7 (2)
C6—N1—C5—O1	−176.7 (2)	C17—C18—N4—C19	−165.4 (2)
N1—C5—O1—C1	173.6 (2)	C18—N4—C19—C20	−135.4 (3)
C5—N1—C6—C7	88.3 (3)	C18—N4—C19—C27	54.2 (3)
N1—C6—C7—O3	65.9 (3)	N4—C19—C20—C21	4.0 (4)
N1—C6—C7—N2	−112.9 (2)	C27—C19—C20—C21	174.3 (2)
O3—C7—N2—C8	1.7 (4)	C19—C20—C21—C22	23.7 (4)
C6—C7—N2—C8	−179.6 (2)	C19—C20—C21—C26	−155.4 (3)
C7—N2—C8—C9	−125.5 (3)	C22—C21—C26—C25	−2.7 (4)
C7—N2—C8—C16	56.8 (3)	C20—C21—C26—C25	176.4 (3)
N2—C8—C9—C10	1.2 (5)	C21—C26—C25—C24	1.4 (5)
C16—C8—C9—C10	178.9 (3)	C26—C25—C24—C23	0.7 (5)
C8—C9—C10—C15	−164.4 (3)	C25—C24—C23—C22	−1.6 (4)
C8—C9—C10—C11	14.6 (5)	C24—C23—C22—C21	0.3 (4)
C11—C10—C15—C14	−1.7 (5)	C26—C21—C22—C23	1.9 (4)
C9—C10—C15—C14	177.4 (3)	C20—C21—C22—C23	−177.2 (2)
C10—C15—C14—C13	1.4 (5)	C20—C19—C27—O6	30.7 (4)
C15—C14—C13—C12	−0.1 (5)	N4—C19—C27—O6	−158.3 (2)
C14—C13—C12—C11	−0.7 (5)	C20—C19—C27—N5	−145.9 (2)
C13—C12—C11—C10	0.4 (5)	N4—C19—C27—N5	25.1 (3)
C15—C10—C11—C12	0.8 (4)	O6—C27—N5—C28	−2.2 (4)
C9—C10—C11—C12	−178.2 (3)	C19—C27—N5—C28	174.4 (2)
C9—C8—C16—O4	25.5 (4)	C27—N5—C28—C29	68.2 (3)
N2—C8—C16—O4	−156.6 (2)	N5—C28—C29—O7	14.8 (4)
C9—C8—C16—N3	−154.3 (2)	N5—C28—C29—O8	−165.5 (2)
N2—C8—C16—N3	23.5 (3)	O7—C29—O8—C30	−2.0 (4)
O4—C16—N3—C17	5.9 (4)	C28—C29—O8—C30	178.3 (2)
C8—C16—N3—C17	−174.2 (2)	C6—N1—C5—O2	4.3 (4)
C16—N3—C17—C18	65.6 (3)	O2—C5—O1—C1	−7.5 (4)
N3—C17—C18—O5	−169.3 (2)	C5—O1—C1—C2	60.1 (4)
N3—C17—C18—N4	9.9 (3)	C5—O1—C1—C4	−65.6 (3)
O5—C18—N4—C19	13.8 (4)	C5—O1—C1—C3	178.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3	0.88	1.99	2.836 (3)	162
N5—H5···O4	0.88	2.18	3.047 (3)	170
N2—H2···O6^i	0.88	1.89	2.738 (3)	160
N3—H3···O5^ii	0.88	2.04	2.857 (3)	155
C4—H4C···O3^iii	0.98	2.50	3.422 (4)	156
C30—H30B···O4^iv	0.98	2.48	3.419 (4)	160
N3—H3···N2	0.88	2.43	2.771 (3)	103
N4—H4···N3	0.88	2.39	2.742 (3)	104
N5—H5···N4	0.88	2.45	2.795 (3)	104
C11—H11A···N2	0.95	2.51	3.100 (4)	120
C22—H22A···N4	0.95	2.58	3.105 (3)	115
C2—H2A···O2	0.98	2.36	2.955 (5)	118
C4—H4A···O2	0.98	2.53	3.089 (4)	116
C9—H9A···O4	0.95	2.48	2.848 (3)	103
C11—H11A···O2	0.95	2.58	3.412 (4)	146
C20—H20A···O6	0.95	2.48	2.839 (3)	102

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