N-{(Amino­carbon­yl)[(S)-4-nitro­benz­yl]meth­yl}-N-{[(R)-cyclo­hexyl](cyclo­hexylamino­carbon­yl)meth­yl}propanamide methanol solvate

The title compound, C₂₆H₃₈N₄O₅·CH₄O, shows typical geometric parameters, and four types of hydrogen bonds form a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.096
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.880     1.000
            Tmin(prime) and Tmax expected:      0.956     0.965
            RR(prime) =      0.889
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....          2
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT756_ALERT_4_C H...A   Calc     2.00000, Rep     2.00(3) ......  Senseless su
              H4   -O6      1.555   2.674
PLAT757_ALERT_4_C D...A   Calc     2.85984, Rep  2.8597(16) ......  Senseless su
              N4   -O6      1.555   2.674
PLAT757_ALERT_4_C D...A   Calc     2.82862, Rep  2.8287(17) ......  Senseless su
              O6   -O3      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C H4 O

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           29.08
           From the CIF: _reflns_number_total               3786
           Count of symmetry unique reflns         3791
           Completeness (_total/calc)             99.87%
           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 C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R

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

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

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-{(Aminocarbonyl)[(S)-4-nitrobenzyl]methyl}-N-{[(R)- cyclohexyl](cyclohexylaminocarbonyl)methyl}propanamide methanol solvate

Crystal data

C26H38N4O5·CH4O	Dx = 1.256 Mg m^−3
Mr = 518.65	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 8641 reflections
Hall symbol: P 4cw	θ = 2.2–28.7°
a = 13.1585 (5) Å	µ = 0.09 mm^−1
c = 15.8470 (13) Å	T = 100 K
V = 2743.8 (3) Å^3	Block, colorless
Z = 4	0.50 × 0.40 × 0.40 mm
F(000) = 1120

Data collection

Bruker SMART1000 CCD area-detector diffractometer	3786 independent reflections
Radiation source: fine-focus sealed tube	3564 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
0.30° ω scans	θmax = 29.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
Tmin = 0.88, Tmax = 1.00	k = −17→17
48333 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0733P)^2 + 0.3284P] where P = (Fo^2 + 2Fc^2)/3
3786 reflections	(Δ/σ)max = 0.007
343 parameters	Δρmax = 0.33 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

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
O1	1.20267 (12)	0.92796 (17)	0.13752 (13)	0.0505 (5)
O2	1.21398 (11)	1.09261 (17)	0.13973 (12)	0.0473 (5)
O3	0.71139 (10)	1.03642 (10)	0.25459 (8)	0.0222 (3)
O4	0.56771 (9)	1.17929 (9)	0.04743 (8)	0.0188 (2)
O5	0.65987 (8)	0.80631 (9)	0.03406 (8)	0.0177 (2)
N1	1.16702 (13)	1.01335 (18)	0.12702 (12)	0.0376 (5)
N2	0.70357 (12)	1.18116 (11)	0.17807 (10)	0.0201 (3)
H2A	0.7202 (19)	1.217 (2)	0.2185 (18)	0.027 (6)*
H2B	0.6801 (17)	1.2066 (18)	0.1342 (17)	0.020 (5)*
N3	0.57060 (9)	1.01182 (9)	0.08022 (8)	0.0130 (2)
N4	0.51247 (10)	0.80583 (10)	−0.04134 (9)	0.0155 (3)
H4	0.4532 (19)	0.8335 (18)	−0.0474 (18)	0.025 (6)*
C1	1.06038 (13)	1.02118 (17)	0.09961 (12)	0.0261 (4)
C2	1.00595 (13)	0.93285 (15)	0.08435 (13)	0.0250 (4)
H2C	1.0369	0.8679	0.0897	0.030*
C3	0.90445 (12)	0.94259 (13)	0.06089 (11)	0.0203 (3)
H3	0.8657	0.8834	0.0491	0.024*
C4	0.85879 (12)	1.03807 (12)	0.05447 (10)	0.0169 (3)
C5	0.91712 (13)	1.12492 (13)	0.06896 (11)	0.0218 (3)
H5	0.8868	1.1901	0.0636	0.026*
C6	1.01903 (13)	1.11728 (15)	0.09112 (12)	0.0259 (4)
H6A	1.0591	1.1763	0.1002	0.031*
C7	0.74792 (12)	1.04609 (12)	0.03126 (10)	0.0159 (3)
H7A	0.7335	1.0005	−0.0170	0.019*
H7B	0.7327	1.1166	0.0134	0.019*
C8	0.67844 (11)	1.01710 (11)	0.10623 (10)	0.0134 (3)
H8	0.6977	0.9459	0.1213	0.016*
C9	0.69766 (11)	1.08048 (12)	0.18697 (10)	0.0152 (3)
C10	0.52272 (12)	1.09721 (11)	0.05049 (10)	0.0144 (3)
C11	0.41259 (12)	1.08962 (12)	0.02302 (11)	0.0180 (3)
H11A	0.3713	1.0637	0.0706	0.022*
H11B	0.4071	1.0404	−0.0240	0.022*
C12	0.37028 (14)	1.19195 (14)	−0.00541 (13)	0.0236 (3)
H12A	0.3741	1.2405	0.0414	0.035*
H12B	0.2993	1.1837	−0.0228	0.035*
H12C	0.4103	1.2174	−0.0531	0.035*
C13	0.52007 (11)	0.91109 (11)	0.08418 (10)	0.0126 (3)
H13	0.4483	0.9203	0.0650	0.015*
C14	0.51695 (11)	0.86840 (11)	0.17426 (10)	0.0137 (3)
H14	0.5883	0.8619	0.1954	0.016*
C15	0.46690 (13)	0.76271 (12)	0.17594 (11)	0.0184 (3)
H15A	0.3971	0.7674	0.1529	0.022*
H15B	0.5062	0.7154	0.1399	0.022*
C16	0.46295 (14)	0.72153 (13)	0.26629 (12)	0.0234 (3)
H16A	0.4279	0.6549	0.2664	0.028*
H16B	0.5331	0.7109	0.2872	0.028*
C17	0.40711 (14)	0.79450 (14)	0.32561 (12)	0.0249 (4)
H17A	0.3348	0.7991	0.3088	0.030*
H17B	0.4100	0.7679	0.3840	0.030*
C18	0.45525 (14)	0.90026 (14)	0.32269 (11)	0.0220 (3)
H18A	0.4153	0.9473	0.3584	0.026*
H18B	0.5251	0.8969	0.3458	0.026*
C19	0.45908 (12)	0.94118 (12)	0.23258 (11)	0.0170 (3)
H19A	0.4929	1.0084	0.2324	0.020*
H19B	0.3890	0.9504	0.2112	0.020*
C20	0.57173 (11)	0.83634 (11)	0.02258 (10)	0.0135 (3)
C21	0.54836 (12)	0.73827 (11)	−0.10837 (10)	0.0148 (3)
H21	0.6071	0.6980	−0.0863	0.018*
C22	0.58437 (13)	0.80033 (13)	−0.18362 (11)	0.0209 (3)
H22A	0.6403	0.8458	−0.1656	0.025*
H22B	0.5278	0.8434	−0.2041	0.025*
C23	0.62157 (14)	0.73262 (16)	−0.25562 (12)	0.0268 (4)
H23A	0.6831	0.6953	−0.2373	0.032*
H23B	0.6402	0.7754	−0.3046	0.032*
C24	0.53947 (14)	0.65675 (15)	−0.28192 (12)	0.0254 (4)
H24A	0.4815	0.6938	−0.3073	0.030*
H24B	0.5672	0.6100	−0.3251	0.030*
C25	0.50243 (15)	0.59549 (13)	−0.20609 (13)	0.0271 (4)
H25A	0.5587	0.5527	−0.1848	0.032*
H25B	0.4466	0.5499	−0.2241	0.032*
C26	0.46455 (7)	0.66475 (7)	−0.13489 (6)	0.0200 (3)
H26A	0.4045	0.7035	−0.1544	0.024*
H26B	0.4438	0.6229	−0.0859	0.024*
O6	0.68356 (7)	1.11280 (7)	0.41983 (6)	0.0255 (3)
H6	0.6930	1.0941	0.3745	0.041 (8)*
C27	0.75769 (7)	1.18107 (7)	0.45291 (6)	0.0297 (4)
H27A	0.7348	1.2067	0.5078	0.045*
H27B	0.7667	1.2381	0.4139	0.045*
H27C	0.8225	1.1453	0.4598	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0249 (7)	0.0756 (13)	0.0509 (11)	0.0195 (8)	−0.0132 (7)	−0.0228 (10)
O2	0.0174 (6)	0.0879 (14)	0.0367 (9)	−0.0161 (7)	0.0029 (6)	−0.0198 (9)
O3	0.0257 (6)	0.0243 (6)	0.0167 (6)	−0.0064 (5)	−0.0041 (5)	0.0024 (5)
O4	0.0214 (5)	0.0151 (5)	0.0198 (6)	−0.0003 (4)	−0.0013 (4)	0.0019 (4)
O5	0.0137 (5)	0.0199 (5)	0.0196 (6)	0.0030 (4)	−0.0015 (4)	−0.0054 (4)
N1	0.0170 (7)	0.0697 (13)	0.0261 (9)	0.0014 (8)	0.0005 (6)	−0.0182 (9)
N2	0.0268 (7)	0.0164 (6)	0.0170 (7)	0.0005 (5)	−0.0058 (6)	−0.0034 (6)
N3	0.0120 (5)	0.0128 (5)	0.0143 (6)	−0.0010 (4)	−0.0010 (5)	−0.0001 (5)
N4	0.0140 (6)	0.0171 (6)	0.0155 (6)	0.0016 (5)	−0.0017 (5)	−0.0046 (5)
C1	0.0144 (7)	0.0464 (11)	0.0174 (8)	−0.0011 (7)	0.0024 (6)	−0.0094 (7)
C2	0.0182 (7)	0.0314 (9)	0.0254 (9)	0.0055 (6)	−0.0003 (7)	−0.0025 (7)
C3	0.0165 (7)	0.0219 (7)	0.0226 (8)	−0.0002 (6)	0.0002 (6)	−0.0025 (6)
C4	0.0143 (6)	0.0215 (7)	0.0147 (7)	−0.0015 (5)	0.0024 (5)	−0.0015 (6)
C5	0.0206 (7)	0.0214 (7)	0.0235 (9)	−0.0045 (6)	0.0048 (6)	−0.0053 (6)
C6	0.0209 (8)	0.0348 (9)	0.0220 (9)	−0.0093 (7)	0.0050 (7)	−0.0105 (7)
C7	0.0143 (6)	0.0186 (7)	0.0148 (7)	0.0003 (5)	0.0011 (5)	0.0002 (5)
C8	0.0105 (6)	0.0161 (6)	0.0135 (7)	0.0005 (5)	−0.0008 (5)	0.0000 (5)
C9	0.0107 (6)	0.0197 (7)	0.0152 (7)	−0.0013 (5)	−0.0008 (5)	−0.0017 (6)
C10	0.0167 (6)	0.0158 (6)	0.0107 (6)	0.0023 (5)	0.0008 (5)	0.0000 (5)
C11	0.0164 (7)	0.0196 (7)	0.0182 (7)	0.0043 (5)	−0.0017 (6)	0.0018 (6)
C12	0.0220 (8)	0.0235 (8)	0.0254 (9)	0.0097 (6)	−0.0021 (7)	0.0036 (7)
C13	0.0117 (6)	0.0129 (6)	0.0131 (6)	−0.0010 (5)	−0.0002 (5)	−0.0016 (5)
C14	0.0146 (6)	0.0148 (6)	0.0116 (6)	−0.0007 (5)	0.0004 (5)	−0.0003 (5)
C15	0.0219 (7)	0.0155 (7)	0.0177 (8)	−0.0032 (5)	0.0014 (6)	−0.0001 (6)
C16	0.0294 (9)	0.0190 (7)	0.0218 (8)	−0.0036 (6)	0.0026 (7)	0.0043 (6)
C17	0.0306 (9)	0.0255 (8)	0.0186 (8)	−0.0069 (7)	0.0053 (7)	0.0010 (7)
C18	0.0279 (8)	0.0243 (8)	0.0139 (7)	−0.0050 (6)	0.0030 (6)	−0.0019 (6)
C19	0.0204 (7)	0.0164 (7)	0.0144 (7)	−0.0006 (5)	0.0030 (6)	−0.0017 (5)
C20	0.0143 (6)	0.0130 (6)	0.0132 (7)	−0.0010 (5)	0.0012 (5)	−0.0011 (5)
C21	0.0167 (7)	0.0142 (6)	0.0136 (7)	0.0014 (5)	−0.0024 (5)	−0.0031 (5)
C22	0.0219 (7)	0.0220 (7)	0.0188 (8)	−0.0007 (6)	0.0035 (6)	−0.0008 (6)
C23	0.0242 (8)	0.0398 (10)	0.0163 (8)	0.0043 (7)	0.0023 (6)	−0.0050 (7)
C24	0.0273 (8)	0.0322 (9)	0.0167 (8)	0.0098 (7)	−0.0060 (7)	−0.0087 (7)
C25	0.0372 (10)	0.0198 (8)	0.0243 (9)	0.0024 (7)	−0.0098 (8)	−0.0080 (7)
C26	0.0239 (8)	0.0192 (7)	0.0169 (8)	−0.0044 (6)	−0.0040 (6)	−0.0020 (6)
O6	0.0210 (6)	0.0278 (6)	0.0275 (7)	−0.0008 (5)	0.0088 (5)	0.0001 (5)
C27	0.0240 (8)	0.0431 (11)	0.0220 (9)	−0.0015 (7)	−0.0004 (7)	0.0029 (8)

Geometric parameters (Å, º)

O1—N1	1.229 (3)	C13—H13	1.0000
O2—N1	1.229 (3)	C14—C19	1.533 (2)
O3—C9	1.232 (2)	C14—C15	1.539 (2)
O4—C10	1.233 (2)	C14—H14	1.0000
O5—C20	1.2387 (19)	C15—C16	1.532 (2)
N1—C1	1.472 (2)	C15—H15A	0.9900
N2—C9	1.335 (2)	C15—H15B	0.9900
N2—H2A	0.83 (3)	C16—C17	1.532 (3)
N2—H2B	0.83 (3)	C16—H16A	0.9900
N3—C10	1.3717 (19)	C16—H16B	0.9900
N3—C8	1.4793 (19)	C17—C18	1.530 (2)
N3—C13	1.4842 (18)	C17—H17A	0.9900
N4—C20	1.340 (2)	C17—H17B	0.9900
N4—C21	1.463 (2)	C18—C19	1.527 (2)
N4—H4	0.87 (2)	C18—H18A	0.9900
C1—C6	1.383 (3)	C18—H18B	0.9900
C1—C2	1.387 (3)	C19—H19A	0.9900
C2—C3	1.392 (2)	C19—H19B	0.9900
C2—H2C	0.9500	C21—C22	1.521 (2)
C3—C4	1.396 (2)	C21—C26	1.5260 (17)
C3—H3	0.9500	C21—H21	1.0000
C4—C5	1.396 (2)	C22—C23	1.528 (2)
C4—C7	1.508 (2)	C22—H22A	0.9900
C5—C6	1.390 (2)	C22—H22B	0.9900
C5—H5	0.9500	C23—C24	1.529 (3)
C6—H6A	0.9500	C23—H23A	0.9900
C7—C8	1.547 (2)	C23—H23B	0.9900
C7—H7A	0.9900	C24—C25	1.527 (3)
C7—H7B	0.9900	C24—H24A	0.9900
C8—C9	1.548 (2)	C24—H24B	0.9900
C8—H8	1.0000	C25—C26	1.534 (2)
C10—C11	1.516 (2)	C25—H25A	0.9900
C11—C12	1.525 (2)	C25—H25B	0.9900
C11—H11A	0.9900	C26—H26A	0.9900
C11—H11B	0.9900	C26—H26B	0.9900
C12—H12A	0.9800	O6—C27	1.4259
C12—H12B	0.9800	O6—H6	0.7695
C12—H12C	0.9800	C27—H27A	0.9800
C13—C14	1.535 (2)	C27—H27B	0.9800
C13—C20	1.544 (2)	C27—H27C	0.9800
O2—N1—O1	124.18 (19)	C14—C15—H15A	109.5
O2—N1—C1	117.9 (2)	C16—C15—H15B	109.5
O1—N1—C1	117.9 (2)	C14—C15—H15B	109.5
C9—N2—H2A	120.3 (18)	H15A—C15—H15B	108.1
C9—N2—H2B	117.8 (17)	C17—C16—C15	111.61 (14)
H2A—N2—H2B	121 (2)	C17—C16—H16A	109.3
C10—N3—C8	119.85 (12)	C15—C16—H16A	109.3
C10—N3—C13	122.71 (12)	C17—C16—H16B	109.3
C8—N3—C13	117.38 (12)	C15—C16—H16B	109.3
C20—N4—C21	122.88 (13)	H16A—C16—H16B	108.0
C20—N4—H4	118.8 (18)	C18—C17—C16	110.68 (14)
C21—N4—H4	117.7 (18)	C18—C17—H17A	109.5
C6—C1—C2	123.11 (17)	C16—C17—H17A	109.5
C6—C1—N1	117.87 (18)	C18—C17—H17B	109.5
C2—C1—N1	119.01 (18)	C16—C17—H17B	109.5
C1—C2—C3	117.70 (17)	H17A—C17—H17B	108.1
C1—C2—H2C	121.1	C19—C18—C17	111.27 (14)
C3—C2—H2C	121.1	C19—C18—H18A	109.4
C2—C3—C4	121.00 (16)	C17—C18—H18A	109.4
C2—C3—H3	119.5	C19—C18—H18B	109.4
C4—C3—H3	119.5	C17—C18—H18B	109.4
C5—C4—C3	119.21 (15)	H18A—C18—H18B	108.0
C5—C4—C7	120.99 (15)	C18—C19—C14	111.09 (13)
C3—C4—C7	119.80 (14)	C18—C19—H19A	109.4
C6—C5—C4	120.86 (16)	C14—C19—H19A	109.4
C6—C5—H5	119.6	C18—C19—H19B	109.4
C4—C5—H5	119.6	C14—C19—H19B	109.4
C1—C6—C5	118.05 (16)	H19A—C19—H19B	108.0
C1—C6—H6A	121.0	O5—C20—N4	124.08 (14)
C5—C6—H6A	121.0	O5—C20—C13	121.52 (14)
C4—C7—C8	111.54 (13)	N4—C20—C13	114.38 (13)
C4—C7—H7A	109.3	N4—C21—C22	110.09 (13)
C8—C7—H7A	109.3	N4—C21—C26	110.59 (12)
C4—C7—H7B	109.3	C22—C21—C26	110.46 (12)
C8—C7—H7B	109.3	N4—C21—H21	108.5
H7A—C7—H7B	108.0	C22—C21—H21	108.5
N3—C8—C7	111.38 (12)	C26—C21—H21	108.5
N3—C8—C9	114.35 (12)	C21—C22—C23	111.85 (14)
C7—C8—C9	113.92 (12)	C21—C22—H22A	109.2
N3—C8—H8	105.4	C23—C22—H22A	109.2
C7—C8—H8	105.4	C21—C22—H22B	109.2
C9—C8—H8	105.4	C23—C22—H22B	109.2
O3—C9—N2	123.42 (15)	H22A—C22—H22B	107.9
O3—C9—C8	119.30 (14)	C22—C23—C24	110.97 (15)
N2—C9—C8	117.19 (14)	C22—C23—H23A	109.4
O4—C10—N3	120.71 (14)	C24—C23—H23A	109.4
O4—C10—C11	120.36 (13)	C22—C23—H23B	109.4
N3—C10—C11	118.92 (13)	C24—C23—H23B	109.4
C10—C11—C12	112.05 (14)	H23A—C23—H23B	108.0
C10—C11—H11A	109.2	C25—C24—C23	110.84 (15)
C12—C11—H11A	109.2	C25—C24—H24A	109.5
C10—C11—H11B	109.2	C23—C24—H24A	109.5
C12—C11—H11B	109.2	C25—C24—H24B	109.5
H11A—C11—H11B	107.9	C23—C24—H24B	109.5
C11—C12—H12A	109.5	H24A—C24—H24B	108.1
C11—C12—H12B	109.5	C24—C25—C26	111.66 (13)
H12A—C12—H12B	109.5	C24—C25—H25A	109.3
C11—C12—H12C	109.5	C26—C25—H25A	109.3
H12A—C12—H12C	109.5	C24—C25—H25B	109.3
H12B—C12—H12C	109.5	C26—C25—H25B	109.3
N3—C13—C14	112.23 (12)	H25A—C25—H25B	107.9
N3—C13—C20	110.18 (12)	C21—C26—C25	110.15 (11)
C14—C13—C20	111.52 (12)	C21—C26—H26A	109.6
N3—C13—H13	107.6	C25—C26—H26A	109.6
C14—C13—H13	107.6	C21—C26—H26B	109.6
C20—C13—H13	107.6	C25—C26—H26B	109.6
C19—C14—C13	110.21 (12)	H26A—C26—H26B	108.1
C19—C14—C15	109.97 (12)	C27—O6—H6	115.7
C13—C14—C15	110.99 (12)	O6—C27—H27A	109.5
C19—C14—H14	108.5	O6—C27—H27B	109.5
C13—C14—H14	108.5	H27A—C27—H27B	109.5
C15—C14—H14	108.5	O6—C27—H27C	109.5
C16—C15—C14	110.51 (13)	H27A—C27—H27C	109.5
C16—C15—H15A	109.5	H27B—C27—H27C	109.5
O2—N1—C1—C6	−1.0 (3)	C10—N3—C13—C14	−121.12 (15)
O1—N1—C1—C6	177.42 (19)	C8—N3—C13—C14	61.65 (16)
O2—N1—C1—C2	179.59 (19)	C10—N3—C13—C20	113.96 (15)
O1—N1—C1—C2	−2.0 (3)	C8—N3—C13—C20	−63.26 (17)
C6—C1—C2—C3	−1.2 (3)	N3—C13—C14—C19	59.54 (15)
N1—C1—C2—C3	178.17 (17)	C20—C13—C14—C19	−176.28 (12)
C1—C2—C3—C4	−1.1 (3)	N3—C13—C14—C15	−178.39 (12)
C2—C3—C4—C5	2.3 (3)	C20—C13—C14—C15	−54.21 (16)
C2—C3—C4—C7	−178.31 (16)	C19—C14—C15—C16	−57.04 (17)
C3—C4—C5—C6	−1.2 (3)	C13—C14—C15—C16	−179.25 (13)
C7—C4—C5—C6	179.38 (16)	C14—C15—C16—C17	56.57 (18)
C2—C1—C6—C5	2.2 (3)	C15—C16—C17—C18	−55.4 (2)
N1—C1—C6—C5	−177.15 (17)	C16—C17—C18—C19	55.3 (2)
C4—C5—C6—C1	−1.0 (3)	C17—C18—C19—C14	−56.91 (18)
C5—C4—C7—C8	−105.39 (18)	C13—C14—C19—C18	−179.87 (13)
C3—C4—C7—C8	75.21 (19)	C15—C14—C19—C18	57.46 (17)
C10—N3—C8—C7	−62.27 (18)	C21—N4—C20—O5	−4.3 (2)
C13—N3—C8—C7	115.03 (14)	C21—N4—C20—C13	177.49 (13)
C10—N3—C8—C9	68.65 (18)	N3—C13—C20—O5	67.30 (18)
C13—N3—C8—C9	−114.04 (14)	C14—C13—C20—O5	−58.02 (18)
C4—C7—C8—N3	−172.47 (12)	N3—C13—C20—N4	−114.45 (14)
C4—C7—C8—C9	56.38 (17)	C14—C13—C20—N4	120.23 (14)
N3—C8—C9—O3	101.56 (16)	C20—N4—C21—C22	−94.66 (18)
C7—C8—C9—O3	−128.76 (15)	C20—N4—C21—C26	142.99 (14)
N3—C8—C9—N2	−81.82 (17)	N4—C21—C22—C23	−179.41 (14)
C7—C8—C9—N2	47.86 (18)	C26—C21—C22—C23	−56.98 (17)
C8—N3—C10—O4	−2.1 (2)	C21—C22—C23—C24	55.6 (2)
C13—N3—C10—O4	−179.26 (14)	C22—C23—C24—C25	−54.3 (2)
C8—N3—C10—C11	179.13 (14)	C23—C24—C25—C26	55.64 (19)
C13—N3—C10—C11	2.0 (2)	N4—C21—C26—C25	179.10 (13)
O4—C10—C11—C12	−0.7 (2)	C22—C21—C26—C25	56.96 (15)
N3—C10—C11—C12	178.07 (15)	C24—C25—C26—C21	−56.96 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5^i	0.83 (3)	2.23 (3)	3.0040 (19)	156 (2)
N2—H2B···O4	0.83 (3)	2.05 (3)	2.735 (2)	139 (2)
N4—H4···O6^ii	0.87 (2)	2.00 (3)	2.8597 (16)	171 (3)
O6—H6···O3	0.77	2.06	2.8287 (17)	176

Symmetry codes: (i) y, −x+2, z+1/4; (ii) −x+1, −y+2, z−1/2.