Matrinium picrolonate 0.28-hydrate

The title compound [systematic name: (7aS*,13aR*,13bR*,13cS*)-10-oxo-dodeca­hydro-1H,5H,8H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridinium 3-methyl-4-nitro-1-(4-nitro­phen­yl)-5-oxo-2-pyrazolinate 0.28-hydrate], C₁₅H₂₅N₂O⁺·C₁₀H₇N₄O₅⁻·0.28H₂O, consists of one matrinium cation [matrine is (7aS,13aR,13bR,13cS)-dodeca­hydro-1H,5H,8H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one], one picrolonate anion and 0.28 water mol­ecules, held together by N—H...O and O—H...O hydrogen bonds. Disordered C atoms in the ring bearing the carbonyl group of the matrinium cation cause the ring to appear in half-chair and half-boat conformations.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.122
• Data-to-parameter ratio = 6.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.39
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      28.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H27C   ..  H13A    ..       2.10 Ang.
PLAT707_ALERT_1_C D...A   Calc   3.222(12), Rep    3.207(5), Dev..       1.25 Sigma
              C23  -O7      1.555   1.555
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.70 Deg.
              C13' -C14  -C13     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.60 Deg.
              C12  -C11  -C12'    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H7 N4 O5

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           25.24
           From the CIF: _reflns_number_total               2353
           Count of symmetry unique reflns         2365
           Completeness (_total/calc)             99.49%
           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
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S

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

   8 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
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(7aS,13aR,13bR,13cS)-10-oxo-dodecahydro-1H,5H,8H-dipyrido[2,1 - f:3',2',1'- ij][1,6]naphthyridinium 3-methyl-4-nitro-1-(4-nitrophenyl)-5-oxo-2-pyrazolinate 0.28-hydrate

Crystal data

C15H25N2O^+·C10H7N4O5^−·0.28H2O	F(000) = 550
Mr = 517.61	Dx = 1.360 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9133 reflections
a = 8.3939 (7) Å	θ = 1.7–23.9°
b = 14.9227 (13) Å	µ = 0.10 mm^−1
c = 10.0939 (9) Å	T = 273 K
β = 92.166 (2)°	Block, colourless
V = 1263.46 (19) Å^3	0.37 × 0.35 × 0.32 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2353 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
Tmin = 0.955, Tmax = 0.961	k = −17→17
6696 measured reflections	l = −7→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.2261P] where P = (Fo^2 + 2Fc^2)/3
2353 reflections	(Δ/σ)max < 0.001
368 parameters	Δρmax = 0.23 e Å^−3
12 restraints	Δρmin = −0.20 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	Occ. (<1)
O7	0.6391 (14)	1.0699 (8)	0.7971 (11)	0.085 (3)*	0.28
H7WA	0.5842	1.0890	0.7336	0.102*	0.28
H7WB	0.6631	1.0168	0.7930	0.102*	0.28
O1	0.6319 (5)	0.9008 (4)	0.7790 (3)	0.1075 (14)
O2	−0.0459 (5)	1.0693 (4)	0.9506 (4)	0.1240 (17)
O3	0.1687 (5)	0.9923 (3)	0.9642 (4)	0.1060 (13)
O4	0.4294 (3)	1.0651 (2)	0.3344 (3)	0.0635 (7)
O5	0.4878 (5)	1.1169 (3)	0.0641 (3)	0.0941 (11)
O6	0.3083 (5)	1.1998 (3)	−0.0342 (3)	0.0957 (11)
N16	0.5444 (4)	0.8831 (2)	0.5684 (3)	0.0594 (9)
N1	0.6002 (4)	0.9256 (2)	0.2128 (3)	0.0534 (8)
N2	0.0754 (5)	1.0404 (3)	0.9042 (4)	0.0827 (12)
N3	0.2057 (4)	1.1469 (2)	0.3863 (3)	0.0540 (8)
N4	0.0962 (4)	1.2065 (3)	0.3253 (4)	0.0698 (10)
N5	0.3625 (5)	1.1596 (3)	0.0659 (4)	0.0762 (11)
C15	0.5330 (5)	0.8706 (3)	0.6996 (4)	0.0670 (11)
C14	0.3949 (7)	0.8176 (4)	0.7475 (4)	0.0874 (16)
C13'	0.3173 (10)	0.7579 (4)	0.6406 (6)	0.064 (3)	0.527 (12)
H13"	0.2241	0.7271	0.6719	0.077*	0.527 (12)
H13'	0.3917	0.7145	0.6070	0.077*	0.527 (12)
C12'	0.2731 (7)	0.8297 (5)	0.5380 (9)	0.051 (3)	0.527 (12)
H12'	0.2280	0.8812	0.5815	0.061*	0.527 (12)
H12"	0.1937	0.8064	0.4748	0.061*	0.527 (12)
C13	0.2532 (9)	0.8191 (9)	0.6469 (8)	0.085 (4)	0.473 (12)
H13A	0.1712	0.7792	0.6777	0.103*	0.473 (12)
H13B	0.2090	0.8792	0.6438	0.103*	0.473 (12)
C12	0.2946 (14)	0.7914 (7)	0.5068 (10)	0.070 (4)	0.473 (12)
H12A	0.2014	0.7947	0.4472	0.084*	0.473 (12)
H12B	0.3357	0.7306	0.5061	0.084*	0.473 (12)
C11	0.4222 (4)	0.8581 (3)	0.4653 (4)	0.0585 (10)
H11	0.3724	0.9118	0.4264	0.070*
C7	0.5003 (5)	0.8024 (2)	0.3581 (5)	0.0641 (11)
H7	0.5383	0.7471	0.4011	0.077*
C8	0.3878 (7)	0.7742 (4)	0.2437 (5)	0.0861 (15)
H8A	0.2922	0.7483	0.2789	0.103*
H8B	0.4390	0.7286	0.1917	0.103*
C9	0.3417 (6)	0.8534 (4)	0.1543 (4)	0.0818 (14)
H9A	0.2731	0.8328	0.0811	0.098*
H9B	0.2832	0.8972	0.2043	0.098*
C10	0.4882 (5)	0.8962 (3)	0.1016 (4)	0.0701 (12)
H10A	0.4577	0.9476	0.0476	0.084*
H10B	0.5420	0.8537	0.0458	0.084*
C2	0.7453 (5)	0.9684 (3)	0.1566 (4)	0.0689 (12)
H2A	0.8009	0.9247	0.1041	0.083*
H2B	0.7129	1.0176	0.0990	0.083*
C3	0.8552 (5)	1.0025 (4)	0.2661 (5)	0.0760 (13)
H3A	0.8016	1.0487	0.3152	0.091*
H3B	0.9488	1.0290	0.2283	0.091*
C4	0.9059 (5)	0.9279 (4)	0.3590 (5)	0.0756 (13)
H4A	0.9703	0.9525	0.4320	0.091*
H4B	0.9712	0.8856	0.3122	0.091*
C5	0.7634 (4)	0.8786 (3)	0.4139 (4)	0.0579 (10)
H5	0.8051	0.8241	0.4569	0.069*
C6	0.6469 (5)	0.8486 (3)	0.3038 (4)	0.0584 (10)
H6	0.7021	0.8043	0.2504	0.070*
C17	0.6796 (5)	0.9316 (3)	0.5192 (4)	0.0604 (10)
H17A	0.7546	0.9443	0.5924	0.072*
H17B	0.6435	0.9883	0.4821	0.072*
C18	0.1119 (5)	1.0677 (3)	0.7690 (4)	0.0590 (10)
C19	−0.0077 (5)	1.1040 (3)	0.6906 (4)	0.0661 (11)
H19	−0.1095	1.1108	0.7224	0.079*
C20	0.0253 (5)	1.1306 (3)	0.5632 (4)	0.0622 (10)
H20	−0.0543	1.1564	0.5091	0.075*
C21	0.1766 (4)	1.1187 (2)	0.5161 (3)	0.0479 (8)
C22	0.2953 (5)	1.0822 (3)	0.5978 (4)	0.0521 (9)
H22	0.3975	1.0748	0.5669	0.063*
C23	0.2627 (5)	1.0568 (3)	0.7248 (4)	0.0598 (10)
H23	0.3424	1.0324	0.7802	0.072*
C24	0.1419 (5)	1.2165 (3)	0.2043 (4)	0.0722 (12)
C25	0.2796 (5)	1.1645 (3)	0.1825 (4)	0.0628 (10)
C26	0.3213 (5)	1.1186 (3)	0.3011 (4)	0.0522 (9)
C27	0.0540 (7)	1.2792 (5)	0.1141 (6)	0.110 (2)
H27A	0.0075	1.2465	0.0404	0.165*
H27B	0.1263	1.3235	0.0823	0.165*
H27C	−0.0287	1.3083	0.1612	0.165*
H14A	0.335 (6)	0.855 (4)	0.806 (5)	0.132*
H14B	0.438 (7)	0.771 (3)	0.805 (5)	0.132*
H1	0.550 (4)	0.967 (3)	0.259 (4)	0.044 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.109 (3)	0.163 (4)	0.0505 (19)	−0.028 (3)	−0.0012 (18)	−0.008 (2)
O2	0.107 (3)	0.192 (5)	0.076 (2)	0.004 (3)	0.040 (2)	0.030 (3)
O3	0.127 (3)	0.128 (3)	0.063 (2)	0.001 (3)	−0.001 (2)	0.041 (2)
O4	0.0790 (18)	0.0594 (16)	0.0530 (15)	0.0160 (16)	0.0150 (13)	0.0039 (14)
O5	0.110 (3)	0.104 (3)	0.070 (2)	0.019 (2)	0.0365 (19)	0.007 (2)
O6	0.140 (3)	0.096 (3)	0.0513 (17)	−0.006 (2)	0.0097 (19)	0.0286 (18)
N16	0.0560 (18)	0.075 (2)	0.0473 (18)	−0.0043 (17)	0.0001 (14)	0.0139 (16)
N1	0.0657 (19)	0.0539 (18)	0.0415 (16)	0.0002 (16)	0.0114 (14)	−0.0031 (14)
N2	0.093 (3)	0.103 (3)	0.052 (2)	−0.014 (3)	0.007 (2)	0.018 (2)
N3	0.0643 (18)	0.0509 (17)	0.0473 (16)	0.0098 (15)	0.0065 (14)	0.0117 (14)
N4	0.073 (2)	0.071 (2)	0.065 (2)	0.0140 (19)	0.0064 (18)	0.0268 (19)
N5	0.108 (3)	0.067 (2)	0.054 (2)	−0.011 (2)	0.017 (2)	0.0071 (19)
C15	0.074 (3)	0.076 (3)	0.051 (2)	0.008 (2)	0.009 (2)	0.005 (2)
C14	0.097 (4)	0.111 (4)	0.056 (3)	−0.005 (3)	0.016 (3)	0.014 (3)
C13'	0.076 (5)	0.042 (4)	0.076 (6)	0.008 (4)	0.026 (4)	0.009 (4)
C12'	0.053 (4)	0.048 (5)	0.050 (6)	0.005 (4)	−0.009 (4)	−0.004 (4)
C13	0.097 (8)	0.093 (9)	0.068 (8)	−0.024 (7)	0.022 (6)	−0.004 (6)
C12	0.084 (7)	0.064 (8)	0.062 (7)	−0.021 (6)	0.015 (5)	−0.004 (6)
C11	0.055 (2)	0.068 (2)	0.052 (2)	−0.0039 (19)	−0.0014 (17)	0.023 (2)
C7	0.079 (3)	0.041 (2)	0.072 (3)	−0.0062 (19)	−0.006 (2)	0.0082 (19)
C8	0.104 (4)	0.072 (3)	0.081 (3)	−0.029 (3)	−0.005 (3)	−0.008 (3)
C9	0.090 (3)	0.099 (4)	0.055 (3)	−0.025 (3)	−0.015 (2)	−0.003 (3)
C10	0.086 (3)	0.082 (3)	0.043 (2)	−0.004 (2)	−0.003 (2)	−0.005 (2)
C2	0.071 (3)	0.082 (3)	0.055 (2)	−0.003 (2)	0.021 (2)	0.002 (2)
C3	0.065 (3)	0.090 (3)	0.074 (3)	−0.019 (2)	0.020 (2)	0.006 (3)
C4	0.057 (2)	0.091 (3)	0.080 (3)	0.003 (2)	0.008 (2)	−0.003 (3)
C5	0.052 (2)	0.058 (2)	0.063 (2)	0.0081 (18)	0.0007 (18)	0.009 (2)
C6	0.068 (2)	0.0423 (19)	0.065 (2)	0.0051 (18)	0.007 (2)	−0.0019 (18)
C17	0.060 (2)	0.071 (3)	0.050 (2)	−0.007 (2)	−0.0028 (18)	0.004 (2)
C18	0.073 (2)	0.059 (2)	0.045 (2)	−0.006 (2)	0.0076 (18)	0.0045 (18)
C19	0.063 (2)	0.077 (3)	0.060 (2)	0.004 (2)	0.015 (2)	0.006 (2)
C20	0.062 (2)	0.066 (2)	0.058 (2)	0.013 (2)	0.0019 (18)	0.014 (2)
C21	0.057 (2)	0.0401 (17)	0.047 (2)	0.0023 (16)	0.0051 (16)	0.0005 (16)
C22	0.058 (2)	0.0504 (19)	0.048 (2)	0.0028 (17)	0.0052 (16)	0.0015 (16)
C23	0.068 (2)	0.060 (2)	0.051 (2)	0.004 (2)	−0.0035 (18)	0.006 (2)
C24	0.080 (3)	0.074 (3)	0.063 (3)	0.002 (2)	0.003 (2)	0.030 (2)
C25	0.080 (3)	0.058 (2)	0.051 (2)	−0.005 (2)	0.011 (2)	0.0129 (19)
C26	0.065 (2)	0.0426 (19)	0.050 (2)	−0.0038 (19)	0.0058 (17)	0.0039 (17)
C27	0.111 (4)	0.128 (5)	0.091 (4)	0.033 (4)	0.014 (3)	0.057 (4)

Geometric parameters (Å, º)

O7—H7WA	0.8253	C7—C6	1.530 (6)
O7—H7WB	0.8199	C7—H7	0.9800
O1—C15	1.219 (6)	C8—C9	1.528 (8)
O2—N2	1.216 (6)	C8—H8A	0.9700
O3—N2	1.208 (5)	C8—H8B	0.9700
O4—C26	1.245 (4)	C9—C10	1.501 (6)
O5—N5	1.230 (5)	C9—H9A	0.9700
O6—N5	1.246 (5)	C9—H9B	0.9700
N16—C15	1.344 (5)	C10—H10A	0.9700
N16—C17	1.449 (5)	C10—H10B	0.9700
N16—C11	1.481 (5)	C2—C3	1.501 (7)
N1—C10	1.503 (5)	C2—H2A	0.9700
N1—C2	1.505 (5)	C2—H2B	0.9700
N1—C6	1.513 (5)	C3—C4	1.506 (7)
N1—H1	0.89 (4)	C3—H3A	0.9700
N2—C18	1.468 (5)	C3—H3B	0.9700
N3—C26	1.387 (5)	C4—C5	1.526 (6)
N3—N4	1.405 (4)	C4—H4A	0.9700
N3—C21	1.406 (4)	C4—H4B	0.9700
N4—C24	1.303 (5)	C5—C17	1.519 (6)
N5—C25	1.392 (5)	C5—C6	1.519 (6)
C15—C14	1.498 (7)	C5—H5	0.9800
C14—C13'	1.526 (3)	C6—H6	0.9800
C14—C13	1.535 (3)	C17—H17A	0.9700
C14—H14A	0.97 (4)	C17—H17B	0.9700
C14—H14B	0.97 (4)	C18—C19	1.366 (6)
C13'—C12'	1.527 (3)	C18—C23	1.368 (6)
C13'—H13"	0.9700	C19—C20	1.384 (6)
C13'—H13'	0.9700	C19—H19	0.9300
C12'—C11	1.534 (3)	C20—C21	1.384 (5)
C12'—H12'	0.9700	C20—H20	0.9300
C12'—H12"	0.9700	C21—C22	1.382 (5)
C13—C12	1.526 (3)	C22—C23	1.374 (5)
C13—H13A	0.9700	C22—H22	0.9300
C13—H13B	0.9700	C23—H23	0.9300
C12—C11	1.532 (3)	C24—C25	1.417 (6)
C12—H12A	0.9700	C24—C27	1.482 (7)
C12—H12B	0.9700	C25—C26	1.411 (6)
C11—C7	1.530 (6)	C27—H27A	0.9600
C11—H11	0.9800	C27—H27B	0.9600
C7—C8	1.523 (6)	C27—H27C	0.9600
H7WA—O7—H7WB	115.2	C10—C9—H9A	109.6
C15—N16—C17	119.5 (3)	C8—C9—H9A	109.6
C15—N16—C11	125.7 (3)	C10—C9—H9B	109.6
C17—N16—C11	114.6 (3)	C8—C9—H9B	109.6
C10—N1—C2	109.5 (3)	H9A—C9—H9B	108.1
C10—N1—C6	111.8 (3)	C9—C10—N1	110.9 (3)
C2—N1—C6	110.8 (3)	C9—C10—H10A	109.5
C10—N1—H1	107 (2)	N1—C10—H10A	109.5
C2—N1—H1	108 (2)	C9—C10—H10B	109.5
C6—N1—H1	109 (2)	N1—C10—H10B	109.5
O3—N2—O2	123.7 (4)	H10A—C10—H10B	108.0
O3—N2—C18	118.5 (4)	C3—C2—N1	110.5 (3)
O2—N2—C18	117.8 (4)	C3—C2—H2A	109.6
C26—N3—N4	112.5 (3)	N1—C2—H2A	109.6
C26—N3—C21	129.5 (3)	C3—C2—H2B	109.6
N4—N3—C21	117.7 (3)	N1—C2—H2B	109.6
C24—N4—N3	105.8 (3)	H2A—C2—H2B	108.1
O5—N5—O6	121.6 (4)	C2—C3—C4	111.0 (4)
O5—N5—C25	119.6 (4)	C2—C3—H3A	109.4
O6—N5—C25	118.8 (4)	C4—C3—H3A	109.4
O1—C15—N16	121.6 (4)	C2—C3—H3B	109.4
O1—C15—C14	119.9 (4)	C4—C3—H3B	109.4
N16—C15—C14	118.5 (4)	H3A—C3—H3B	108.0
C15—C14—C13'	113.2 (4)	C3—C4—C5	112.1 (3)
C15—C14—C13	111.6 (5)	C3—C4—H4A	109.2
C13'—C14—C13	40.7 (5)	C5—C4—H4A	109.2
C15—C14—H14A	108 (4)	C3—C4—H4B	109.2
C13'—C14—H14A	124 (4)	C5—C4—H4B	109.2
C13—C14—H14A	89 (4)	H4A—C4—H4B	107.9
C15—C14—H14B	107 (4)	C17—C5—C6	111.3 (3)
C13'—C14—H14B	98 (4)	C17—C5—C4	113.1 (4)
C13—C14—H14B	132 (4)	C6—C5—C4	111.6 (3)
H14A—C14—H14B	104 (5)	C17—C5—H5	106.8
C14—C13'—C12'	99.0 (6)	C6—C5—H5	106.8
C14—C13'—H13"	112.0	C4—C5—H5	106.8
C12'—C13'—H13"	112.0	N1—C6—C5	111.4 (3)
C14—C13'—H13'	112.0	N1—C6—C7	111.5 (3)
C12'—C13'—H13'	112.0	C5—C6—C7	112.0 (3)
H13"—C13'—H13'	109.7	N1—C6—H6	107.2
C13'—C12'—C11	109.7 (5)	C5—C6—H6	107.2
C13'—C12'—H12'	109.7	C7—C6—H6	107.2
C11—C12'—H12'	109.7	N16—C17—C5	111.6 (3)
C13'—C12'—H12"	109.7	N16—C17—H17A	109.3
C11—C12'—H12"	109.7	C5—C17—H17A	109.3
H12'—C12'—H12"	108.2	N16—C17—H17B	109.3
C12—C13—C14	114.3 (8)	C5—C17—H17B	109.3
C12—C13—H13A	108.7	H17A—C17—H17B	108.0
C14—C13—H13A	108.7	C19—C18—C23	121.8 (4)
C12—C13—H13B	108.7	C19—C18—N2	118.3 (4)
C14—C13—H13B	108.7	C23—C18—N2	119.9 (4)
H13A—C13—H13B	107.6	C18—C19—C20	118.9 (4)
C13—C12—C11	105.3 (7)	C18—C19—H19	120.5
C13—C12—H12A	110.7	C20—C19—H19	120.5
C11—C12—H12A	110.7	C21—C20—C19	120.1 (4)
C13—C12—H12B	110.7	C21—C20—H20	120.0
C11—C12—H12B	110.7	C19—C20—H20	120.0
H12A—C12—H12B	108.8	C22—C21—C20	119.7 (3)
N16—C11—C7	109.3 (3)	C22—C21—N3	121.9 (3)
N16—C11—C12	116.4 (5)	C20—C21—N3	118.4 (3)
C7—C11—C12	99.4 (5)	C23—C22—C21	120.1 (4)
N16—C11—C12'	106.8 (4)	C23—C22—H22	120.0
C7—C11—C12'	124.6 (5)	C21—C22—H22	120.0
C12—C11—C12'	25.6 (4)	C18—C23—C22	119.4 (4)
N16—C11—H11	110.4	C18—C23—H23	120.3
C7—C11—H11	110.4	C22—C23—H23	120.3
C12—C11—H11	110.4	N4—C24—C25	110.7 (4)
C12'—C11—H11	94.2	N4—C24—C27	119.4 (5)
C8—C7—C6	109.7 (4)	C25—C24—C27	129.9 (4)
C8—C7—C11	114.6 (4)	N5—C25—C26	125.2 (4)
C6—C7—C11	112.4 (3)	N5—C25—C24	126.6 (4)
C8—C7—H7	106.6	C26—C25—C24	108.2 (4)
C6—C7—H7	106.6	O4—C26—N3	123.2 (3)
C11—C7—H7	106.6	O4—C26—C25	134.0 (4)
C7—C8—C9	111.7 (4)	N3—C26—C25	102.7 (3)
C7—C8—H8A	109.3	C24—C27—H27A	109.5
C9—C8—H8A	109.3	C24—C27—H27B	109.5
C7—C8—H8B	109.3	H27A—C27—H27B	109.5
C9—C8—H8B	109.3	C24—C27—H27C	109.5
H8A—C8—H8B	107.9	H27A—C27—H27C	109.5
C10—C9—C8	110.2 (4)	H27B—C27—H27C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
07—H7WA···O1	0.83 (2)	1.95 (2)	2.832 (5)	171 (4)
N1—H1···O4	0.89 (4)	1.95 (4)	2.832 (5)	171 (4)
C2—H2B···O5	0.97	2.42	3.209 (6)	139
C8—H8B···O7^i	0.97	2.47	3.088 (6)	121
C10—H10A···O5	0.97	2.55	3.317 (7)	136
C11—H11···O4	0.98	2.52	3.362 (5)	144
C13—H13A···N4^ii	0.97	2.50	3.404 (6)	156
C17—H17B···O4	0.97	2.56	3.401 (5)	145
C19—H19···O7^iii	0.93	2.35	3.237 (6)	158
C23—H23···O7	0.93	2.54	3.207 (5)	129

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