3-[3-(4-Ethoxy­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-4-nitro-2,5-diphenyl­isoxazolidine

The isoxazolidine ring in the title compound, C₃₂H₂₈N₄O₄, adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.144
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.81 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C4     -C9            1.37 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

3-[3-(4-Ethoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]-4-nitro-2,5- diphenylisoxazolidine

Crystal data

C32H28N4O4	F(000) = 1120
Mr = 532.58	Dx = 1.300 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3064 reflections
a = 13.2463 (7) Å	θ = 1.7–25.0°
b = 10.0112 (6) Å	µ = 0.09 mm^−1
c = 20.9518 (12) Å	T = 273 K
β = 101.688 (1)°	Block, colorless
V = 2720.8 (3) Å^3	0.27 × 0.24 × 0.23 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
ω scans	h = −17→17
30188 measured reflections	k = −12→12
6286 independent reflections	l = −27→27

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) = 0.144	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0719P)^2 + 0.6715P] where P = (Fo^2 + 2Fc^2)/3
6286 reflections	(Δ/σ)max = 0.001
362 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.18 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
C1	0.82347 (11)	0.75031 (14)	0.20783 (7)	0.0371 (3)
C2	0.88236 (10)	0.64658 (13)	0.18798 (6)	0.0353 (3)
C3	0.85709 (11)	0.65014 (14)	0.12109 (7)	0.0392 (3)
H3	0.8824	0.5938	0.0927	0.047*
C4	0.74164 (12)	0.79249 (15)	0.03997 (7)	0.0429 (3)
C5	0.65294 (16)	0.8657 (2)	0.02967 (9)	0.0760 (6)
H5	0.6216	0.8872	0.0642	0.091*
C6	0.61008 (19)	0.9075 (3)	−0.03313 (10)	0.0914 (8)
H6	0.5499	0.9580	−0.0402	0.110*
C7	0.65397 (17)	0.8766 (2)	−0.08436 (9)	0.0686 (5)
H7	0.6242	0.9052	−0.1262	0.082*
C8	0.74188 (18)	0.8034 (2)	−0.07375 (9)	0.0740 (6)
H8	0.7722	0.7808	−0.1086	0.089*
C9	0.78676 (15)	0.7620 (2)	−0.01163 (8)	0.0658 (5)
H9	0.8478	0.7132	−0.0047	0.079*
C10	0.82407 (11)	0.79573 (14)	0.27500 (7)	0.0389 (3)
C11	0.81059 (12)	0.70778 (16)	0.32382 (7)	0.0467 (4)
H11	0.7980	0.6180	0.3140	0.056*
C12	0.81568 (14)	0.75232 (18)	0.38705 (8)	0.0554 (4)
H12	0.8065	0.6926	0.4194	0.067*
C13	0.83452 (13)	0.88576 (18)	0.40191 (8)	0.0525 (4)
C14	0.84713 (13)	0.97433 (17)	0.35360 (8)	0.0494 (4)
H14	0.8590	1.0643	0.3634	0.059*
C15	0.84219 (12)	0.92978 (15)	0.29109 (7)	0.0439 (3)
H15	0.8511	0.9901	0.2589	0.053*
C16	0.8606 (2)	0.8570 (3)	0.51703 (10)	0.0851 (7)
H16A	0.9228	0.8056	0.5171	0.102*
H16B	0.8039	0.7954	0.5161	0.102*
C17	0.8742 (2)	0.9429 (3)	0.57652 (10)	0.0990 (8)
H17A	0.9266	1.0084	0.5751	0.148*
H17B	0.8943	0.8884	0.6147	0.148*
H17C	0.8104	0.9871	0.5780	0.148*
C18	0.95975 (10)	0.56158 (13)	0.23191 (6)	0.0351 (3)
H18	0.9579	0.5835	0.2772	0.042*
C19	0.94378 (11)	0.41151 (14)	0.22215 (7)	0.0384 (3)
H19	0.8741	0.3927	0.1975	0.046*
C20	1.02588 (12)	0.36874 (14)	0.18225 (7)	0.0420 (3)
H20	1.0810	0.3187	0.2106	0.050*
C21	0.98569 (12)	0.28848 (16)	0.12157 (8)	0.0487 (4)
C22	0.96503 (18)	0.1540 (2)	0.12763 (12)	0.0737 (6)
H22	0.9771	0.1146	0.1687	0.088*
C23	0.9265 (2)	0.0780 (3)	0.07299 (16)	0.0969 (8)
H23	0.9122	−0.0120	0.0776	0.116*
C24	0.90946 (19)	0.1342 (3)	0.01230 (15)	0.0941 (8)
H24	0.8835	0.0827	−0.0243	0.113*
C25	0.93082 (19)	0.2666 (3)	0.00567 (11)	0.0849 (7)
H25	0.9195	0.3051	−0.0356	0.102*
C26	0.96929 (16)	0.3439 (2)	0.06020 (9)	0.0639 (5)
H26	0.9841	0.4337	0.0552	0.077*
C27	1.10916 (11)	0.70041 (14)	0.21514 (7)	0.0401 (3)
C28	1.17832 (13)	0.71813 (18)	0.17430 (8)	0.0536 (4)
H28	1.1937	0.6475	0.1491	0.064*
C29	1.22437 (15)	0.8416 (2)	0.17128 (10)	0.0676 (5)
H29	1.2705	0.8536	0.1437	0.081*
C30	1.20277 (16)	0.9463 (2)	0.20851 (10)	0.0668 (5)
H30	1.2336	1.0291	0.2059	0.080*
C31	1.13527 (15)	0.92827 (18)	0.24973 (9)	0.0616 (5)
H31	1.1211	0.9989	0.2754	0.074*
C32	1.08819 (13)	0.80589 (16)	0.25337 (8)	0.0494 (4)
H32	1.0426	0.7944	0.2814	0.059*
N1	0.78884 (9)	0.75030 (12)	0.10406 (6)	0.0398 (3)
N2	0.76689 (10)	0.81367 (12)	0.15705 (6)	0.0428 (3)
N3	1.06731 (9)	0.57279 (11)	0.22290 (6)	0.0381 (3)
N4	0.96428 (11)	0.33557 (13)	0.28594 (7)	0.0495 (3)
O1	0.84005 (13)	0.94125 (15)	0.46225 (6)	0.0771 (4)
O2	0.98620 (13)	0.39394 (14)	0.33721 (6)	0.0740 (4)
O3	0.95819 (15)	0.21518 (13)	0.28165 (7)	0.0897 (5)
O4	1.06582 (8)	0.49269 (10)	0.16493 (5)	0.0436 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0378 (7)	0.0360 (7)	0.0371 (7)	0.0006 (6)	0.0065 (5)	0.0008 (5)
C2	0.0341 (7)	0.0340 (7)	0.0372 (7)	−0.0011 (5)	0.0062 (5)	0.0006 (5)
C3	0.0408 (7)	0.0395 (7)	0.0367 (7)	0.0035 (6)	0.0068 (6)	−0.0004 (6)
C4	0.0457 (8)	0.0436 (8)	0.0366 (7)	−0.0005 (6)	0.0016 (6)	0.0042 (6)
C5	0.0750 (13)	0.1073 (17)	0.0455 (10)	0.0430 (12)	0.0114 (9)	0.0128 (10)
C6	0.0856 (15)	0.127 (2)	0.0572 (12)	0.0548 (15)	0.0047 (11)	0.0208 (13)
C7	0.0782 (13)	0.0797 (13)	0.0414 (9)	0.0094 (11)	−0.0031 (9)	0.0123 (9)
C8	0.0887 (15)	0.0933 (16)	0.0405 (9)	0.0195 (12)	0.0146 (9)	0.0101 (9)
C9	0.0653 (11)	0.0876 (14)	0.0447 (9)	0.0236 (10)	0.0115 (8)	0.0089 (9)
C10	0.0376 (7)	0.0413 (7)	0.0377 (7)	0.0066 (6)	0.0073 (6)	−0.0013 (6)
C11	0.0543 (9)	0.0430 (8)	0.0439 (8)	−0.0007 (7)	0.0122 (7)	−0.0004 (6)
C12	0.0692 (11)	0.0575 (10)	0.0417 (8)	0.0017 (8)	0.0162 (8)	0.0062 (7)
C13	0.0546 (9)	0.0618 (10)	0.0411 (8)	0.0073 (8)	0.0095 (7)	−0.0091 (7)
C14	0.0543 (9)	0.0439 (8)	0.0500 (9)	0.0048 (7)	0.0104 (7)	−0.0088 (7)
C15	0.0472 (8)	0.0399 (8)	0.0453 (8)	0.0064 (6)	0.0107 (6)	0.0016 (6)
C16	0.1025 (18)	0.1028 (18)	0.0510 (11)	0.0104 (14)	0.0176 (11)	−0.0002 (11)
C17	0.116 (2)	0.133 (2)	0.0453 (11)	0.0035 (18)	0.0119 (12)	−0.0095 (13)
C18	0.0354 (7)	0.0346 (7)	0.0345 (7)	0.0001 (5)	0.0052 (5)	0.0004 (5)
C19	0.0397 (7)	0.0351 (7)	0.0386 (7)	−0.0009 (6)	0.0037 (6)	0.0036 (6)
C20	0.0421 (8)	0.0340 (7)	0.0490 (8)	0.0032 (6)	0.0070 (6)	−0.0001 (6)
C21	0.0446 (8)	0.0443 (8)	0.0573 (9)	0.0051 (7)	0.0106 (7)	−0.0117 (7)
C22	0.0896 (15)	0.0496 (11)	0.0833 (14)	−0.0069 (10)	0.0206 (11)	−0.0163 (10)
C23	0.1011 (19)	0.0668 (14)	0.125 (2)	−0.0216 (13)	0.0273 (17)	−0.0468 (15)
C24	0.0772 (15)	0.107 (2)	0.0947 (19)	−0.0032 (14)	0.0090 (13)	−0.0604 (16)
C25	0.0870 (16)	0.1017 (19)	0.0615 (13)	0.0179 (13)	0.0049 (11)	−0.0303 (12)
C26	0.0735 (12)	0.0626 (11)	0.0542 (10)	0.0108 (9)	0.0096 (9)	−0.0137 (8)
C27	0.0355 (7)	0.0405 (7)	0.0404 (7)	−0.0033 (6)	−0.0019 (6)	0.0028 (6)
C28	0.0518 (9)	0.0561 (10)	0.0539 (9)	−0.0109 (8)	0.0131 (7)	−0.0016 (8)
C29	0.0639 (11)	0.0742 (13)	0.0666 (12)	−0.0258 (10)	0.0179 (9)	0.0045 (10)
C30	0.0687 (12)	0.0556 (11)	0.0701 (12)	−0.0276 (9)	−0.0001 (9)	0.0037 (9)
C31	0.0683 (11)	0.0468 (10)	0.0641 (11)	−0.0132 (8)	0.0002 (9)	−0.0085 (8)
C32	0.0503 (9)	0.0464 (9)	0.0500 (9)	−0.0070 (7)	0.0062 (7)	−0.0049 (7)
N1	0.0426 (6)	0.0412 (6)	0.0344 (6)	0.0053 (5)	0.0048 (5)	0.0019 (5)
N2	0.0465 (7)	0.0430 (7)	0.0379 (6)	0.0084 (5)	0.0064 (5)	0.0007 (5)
N3	0.0371 (6)	0.0362 (6)	0.0402 (6)	0.0001 (5)	0.0063 (5)	−0.0020 (5)
N4	0.0574 (8)	0.0409 (7)	0.0495 (8)	−0.0026 (6)	0.0095 (6)	0.0099 (6)
O1	0.1089 (12)	0.0811 (10)	0.0412 (7)	0.0112 (8)	0.0152 (7)	−0.0104 (6)
O2	0.1128 (12)	0.0620 (8)	0.0432 (7)	−0.0114 (8)	0.0061 (7)	0.0083 (6)
O3	0.1530 (16)	0.0395 (7)	0.0757 (10)	−0.0050 (8)	0.0208 (10)	0.0151 (6)
O4	0.0472 (6)	0.0391 (5)	0.0470 (6)	−0.0025 (4)	0.0157 (5)	−0.0053 (4)

Geometric parameters (Å, º)

C1—N2	1.331 (2)	C18—N3	1.479 (2)
C1—C2	1.411 (2)	C18—C19	1.5252 (19)
C1—C10	1.478 (2)	C18—H18	0.9800
C2—C3	1.374 (2)	C19—N4	1.5137 (18)
C2—C18	1.497 (2)	C19—C20	1.560 (2)
C3—N1	1.349 (2)	C19—H19	0.9800
C3—H3	0.9300	C20—O4	1.425 (2)
C4—C5	1.364 (2)	C20—C21	1.507 (2)
C4—C9	1.372 (2)	C20—H20	0.9800
C4—N1	1.426 (2)	C21—C26	1.377 (3)
C5—C6	1.388 (3)	C21—C22	1.385 (3)
C5—H5	0.9300	C22—C23	1.383 (3)
C6—C7	1.356 (3)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.367 (4)
C7—C8	1.356 (3)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.369 (4)
C8—C9	1.380 (2)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.389 (3)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.388 (2)	C26—H26	0.9300
C10—C15	1.393 (2)	C27—C28	1.386 (2)
C11—C12	1.387 (2)	C27—C32	1.387 (2)
C11—H11	0.9300	C27—N3	1.4151 (18)
C12—C13	1.383 (3)	C28—C29	1.386 (2)
C12—H12	0.9300	C28—H28	0.9300
C13—O1	1.369 (2)	C29—C30	1.371 (3)
C13—C14	1.381 (2)	C29—H29	0.9300
C14—C15	1.372 (2)	C30—C31	1.375 (3)
C14—H14	0.9300	C30—H30	0.9300
C15—H15	0.9300	C31—C32	1.384 (2)
C16—O1	1.406 (3)	C31—H31	0.9300
C16—C17	1.495 (3)	C32—H32	0.9300
C16—H16A	0.9700	N1—N2	1.360 (2)
C16—H16B	0.9700	N3—O4	1.452 (2)
C17—H17A	0.9600	N4—O2	1.205 (2)
C17—H17B	0.9600	N4—O3	1.210 (2)
C17—H17C	0.9600
N2—C1—C2	111.74 (12)	C19—C18—H18	108.7
N2—C1—C10	120.53 (12)	N4—C19—C18	112.40 (12)
C2—C1—C10	127.63 (12)	N4—C19—C20	108.39 (11)
C3—C2—C1	104.27 (12)	C18—C19—C20	104.45 (11)
C3—C2—C18	129.58 (12)	N4—C19—H19	110.5
C1—C2—C18	126.00 (12)	C18—C19—H19	110.5
N1—C3—C2	107.51 (12)	C20—C19—H19	110.5
N1—C3—H3	126.2	O4—C20—C21	109.60 (12)
C2—C3—H3	126.2	O4—C20—C19	103.45 (11)
C5—C4—C9	119.59 (15)	C21—C20—C19	115.66 (12)
C5—C4—N1	120.49 (14)	O4—C20—H20	109.3
C9—C4—N1	119.90 (14)	C21—C20—H20	109.3
C4—C5—C6	119.07 (18)	C19—C20—H20	109.3
C4—C5—H5	120.5	C26—C21—C22	118.75 (17)
C6—C5—H5	120.5	C26—C21—C20	122.33 (16)
C7—C6—C5	121.5 (2)	C22—C21—C20	118.92 (17)
C7—C6—H6	119.2	C23—C22—C21	120.4 (2)
C5—C6—H6	119.2	C23—C22—H22	119.8
C6—C7—C8	119.04 (17)	C21—C22—H22	119.8
C6—C7—H7	120.5	C24—C23—C22	120.5 (2)
C8—C7—H7	120.5	C24—C23—H23	119.8
C7—C8—C9	120.56 (19)	C22—C23—H23	119.8
C7—C8—H8	119.7	C23—C24—C25	119.6 (2)
C9—C8—H8	119.7	C23—C24—H24	120.2
C4—C9—C8	120.21 (18)	C25—C24—H24	120.2
C4—C9—H9	119.9	C24—C25—C26	120.4 (2)
C8—C9—H9	119.9	C24—C25—H25	119.8
C11—C10—C15	118.32 (14)	C26—C25—H25	119.8
C11—C10—C1	122.00 (13)	C21—C26—C25	120.4 (2)
C15—C10—C1	119.64 (13)	C21—C26—H26	119.8
C12—C11—C10	120.76 (15)	C25—C26—H26	119.8
C12—C11—H11	119.6	C28—C27—C32	119.59 (14)
C10—C11—H11	119.6	C28—C27—N3	120.66 (14)
C13—C12—C11	119.83 (15)	C32—C27—N3	119.47 (13)
C13—C12—H12	120.1	C29—C28—C27	119.65 (17)
C11—C12—H12	120.1	C29—C28—H28	120.2
O1—C13—C14	115.12 (16)	C27—C28—H28	120.2
O1—C13—C12	124.98 (16)	C30—C29—C28	120.77 (18)
C14—C13—C12	119.89 (15)	C30—C29—H29	119.6
C15—C14—C13	120.09 (15)	C28—C29—H29	119.6
C15—C14—H14	120.0	C29—C30—C31	119.60 (17)
C13—C14—H14	120.0	C29—C30—H30	120.2
C14—C15—C10	121.12 (14)	C31—C30—H30	120.2
C14—C15—H15	119.4	C30—C31—C32	120.57 (18)
C10—C15—H15	119.4	C30—C31—H31	119.7
O1—C16—C17	107.8 (2)	C32—C31—H31	119.7
O1—C16—H16A	110.1	C31—C32—C27	119.80 (16)
C17—C16—H16A	110.1	C31—C32—H32	120.1
O1—C16—H16B	110.1	C27—C32—H32	120.1
C17—C16—H16B	110.1	C3—N1—N2	111.9 (1)
H16A—C16—H16B	108.5	C3—N1—C4	127.7 (1)
C16—C17—H17A	109.5	N2—N1—C4	120.3 (1)
C16—C17—H17B	109.5	C1—N2—N1	104.6 (1)
H17A—C17—H17B	109.5	C27—N3—O4	110.0 (1)
C16—C17—H17C	109.5	C27—N3—C18	119.5 (1)
H17A—C17—H17C	109.5	O4—N3—C18	102.4 (1)
H17B—C17—H17C	109.5	O2—N4—O3	123.3 (2)
N3—C18—C2	115.85 (11)	O2—N4—C19	120.7 (1)
N3—C18—C19	99.71 (11)	O3—N4—C19	115.9 (1)
C2—C18—C19	114.74 (11)	C13—O1—C16	118.4 (2)
N3—C18—H18	108.7	C20—O4—N3	102.2 (1)
C2—C18—H18	108.7
N2—C1—C2—C3	−0.49 (16)	C20—C21—C22—C23	178.98 (19)
C10—C1—C2—C3	−176.88 (14)	C21—C22—C23—C24	0.7 (4)
N2—C1—C2—C18	175.46 (13)	C22—C23—C24—C25	0.1 (4)
C10—C1—C2—C18	−0.9 (2)	C23—C24—C25—C26	−0.2 (4)
C1—C2—C3—N1	0.48 (15)	C22—C21—C26—C25	1.2 (3)
C18—C2—C3—N1	−175.26 (13)	C20—C21—C26—C25	−179.12 (17)
C9—C4—C5—C6	0.1 (4)	C24—C25—C26—C21	−0.5 (3)
N1—C4—C5—C6	178.7 (2)	C32—C27—C28—C29	−1.1 (2)
C4—C5—C6—C7	0.4 (4)	N3—C27—C28—C29	−175.05 (15)
C5—C6—C7—C8	−0.2 (4)	C27—C28—C29—C30	0.4 (3)
C6—C7—C8—C9	−0.7 (4)	C28—C29—C30—C31	0.5 (3)
C5—C4—C9—C8	−1.0 (3)	C29—C30—C31—C32	−0.7 (3)
N1—C4—C9—C8	−179.52 (18)	C30—C31—C32—C27	0.0 (3)
C7—C8—C9—C4	1.2 (4)	C28—C27—C32—C31	0.9 (2)
N2—C1—C10—C11	131.71 (16)	N3—C27—C32—C31	174.94 (14)
C2—C1—C10—C11	−52.2 (2)	C2—C3—N1—N2	−0.34 (17)
N2—C1—C10—C15	−50.6 (2)	C2—C3—N1—C4	179.40 (13)
C2—C1—C10—C15	125.54 (16)	C5—C4—N1—C3	159.95 (19)
C15—C10—C11—C12	−0.4 (2)	C9—C4—N1—C3	−21.5 (2)
C1—C10—C11—C12	177.36 (15)	C5—C4—N1—N2	−20.3 (2)
C10—C11—C12—C13	−0.1 (3)	C9—C4—N1—N2	158.22 (16)
C11—C12—C13—O1	179.23 (17)	C2—C1—N2—N1	0.28 (16)
C11—C12—C13—C14	0.7 (3)	C10—C1—N2—N1	176.97 (12)
O1—C13—C14—C15	−179.47 (15)	C3—N1—N2—C1	0.04 (16)
C12—C13—C14—C15	−0.8 (3)	C4—N1—N2—C1	−179.72 (12)
C13—C14—C15—C10	0.3 (2)	C28—C27—N3—O4	−26.86 (18)
C11—C10—C15—C14	0.3 (2)	C32—C27—N3—O4	159.20 (13)
C1—C10—C15—C14	−177.52 (14)	C28—C27—N3—C18	−144.80 (14)
C3—C2—C18—N3	57.96 (19)	C32—C27—N3—C18	41.26 (19)
C1—C2—C18—N3	−116.94 (15)	C2—C18—N3—C27	43.97 (17)
C3—C2—C18—C19	−57.5 (2)	C19—C18—N3—C27	167.65 (12)
C1—C2—C18—C19	127.62 (14)	C2—C18—N3—O4	−77.81 (13)
N3—C18—C19—N4	95.12 (13)	C19—C18—N3—O4	45.87 (11)
C2—C18—C19—N4	−140.42 (12)	C18—C19—N4—O2	2.9 (2)
N3—C18—C19—C20	−22.17 (13)	C20—C19—N4—O2	117.85 (16)
C2—C18—C19—C20	102.28 (13)	C18—C19—N4—O3	−176.36 (15)
N4—C19—C20—O4	−128.90 (12)	C20—C19—N4—O3	−61.44 (18)
C18—C19—C20—O4	−8.88 (14)	C14—C13—O1—C16	−160.22 (19)
N4—C19—C20—C21	111.26 (14)	C12—C13—O1—C16	21.2 (3)
C18—C19—C20—C21	−128.72 (13)	C17—C16—O1—C13	173.83 (19)
O4—C20—C21—C26	−14.1 (2)	C21—C20—O4—N3	161.23 (11)
C19—C20—C21—C26	102.35 (18)	C19—C20—O4—N3	37.33 (12)
O4—C20—C21—C22	165.56 (16)	C27—N3—O4—C20	177.88 (11)
C19—C20—C21—C22	−78.01 (19)	C18—N3—O4—C20	−54.02 (12)
C26—C21—C22—C23	−1.4 (3)