N′-tert-Butyl-N'-(3,5-di­methyl­benzoyl)-N-(4-carboxy­phenoxy)­oxalyl-N-(4-ethyl­benzoyl)­hydrazine

The title compound, C₃₁H₃₂N₂O₇, was synthesized by hydrogenation of N′-tert-butyl-N′-(3,5-di­methyl­benzoyl)-N-(4-benzyl­oxyl­carbonyl­phenoxy)­oxalyl-N-(4-ethyl­benzoyl)­hydra­zine using palladium on carbon as catalyst. In the crystal structure, the mol­ecules are linked via intermolecular O—H...O hydrogen bonds, forming chains. In addition, intermolecular C—H...O hydrogen bonds and C—H...π interactions are observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.151
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.89 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.10 Ratio

Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B   ..  CG3     ..       2.80 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30    ..  CG2     ..       2.82 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 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
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N'-tert-Butyl-N'-(3,5-dimethylbenzoyl)-N-(4-carboxyphenoxy)oxalyl- N-(4-ethylbenzoyl)hydrazine

Crystal data

C31H32N2O7	Z = 2
Mr = 544.59	F(000) = 576
Triclinic, P1	Dx = 1.220 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.971 (4) Å	Cell parameters from 738 reflections
b = 13.239 (5) Å	θ = 2.3–23.5°
c = 13.649 (5) Å	µ = 0.09 mm^−1
α = 111.141 (6)°	T = 293 K
β = 103.553 (6)°	Prism, colourless
γ = 107.231 (6)°	0.28 × 0.22 × 0.20 mm
V = 1482.7 (10) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
φ and ω scans	h = −11→11
7682 measured reflections	k = −15→10
5192 independent reflections	l = −16→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0687P)^2 + 0.2554P] where P = (Fo^2 + 2Fc^2)/3
5192 reflections	(Δ/σ)max < 0.001
368 parameters	Δρmax = 0.21 e Å^−3
0 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
N1	0.6676 (2)	0.69375 (17)	0.34408 (15)	0.0451 (5)
N2	0.6736 (2)	0.75617 (16)	0.45356 (15)	0.0390 (5)
O1	0.7931 (3)	0.61289 (18)	0.24637 (16)	0.0772 (6)
O2	0.4851 (2)	0.59205 (17)	0.42924 (15)	0.0632 (5)
O3	0.8314 (2)	0.92937 (15)	0.46759 (15)	0.0605 (5)
O4	0.5887 (2)	0.94448 (17)	0.58646 (15)	0.0636 (5)
O5	0.8411 (2)	1.03205 (15)	0.69160 (15)	0.0557 (5)
O6	0.8700 (3)	1.46375 (17)	1.10505 (17)	0.0729 (6)
H6	0.8531	1.5052	1.1577	0.109*
O7	0.7067 (3)	1.31638 (19)	1.11520 (18)	0.0840 (7)
C1	0.7809 (3)	0.6583 (2)	0.3380 (2)	0.0501 (7)
C2	0.8887 (3)	0.6759 (2)	0.4451 (2)	0.0455 (6)
C3	0.8492 (3)	0.5941 (2)	0.4858 (2)	0.0503 (7)
H3	0.7543	0.5295	0.4467	0.060*
C4	0.9489 (3)	0.6070 (2)	0.5837 (2)	0.0525 (7)
C5	1.0898 (3)	0.7032 (3)	0.6391 (2)	0.0593 (7)
H5	1.1582	0.7123	0.7045	0.071*
C6	1.1325 (3)	0.7862 (2)	0.6003 (3)	0.0597 (8)
C7	1.0299 (3)	0.7711 (2)	0.5024 (2)	0.0545 (7)
H7	1.0566	0.8258	0.4748	0.065*
C8	0.9026 (4)	0.5216 (3)	0.6307 (3)	0.0730 (9)
H8A	0.8483	0.5465	0.6772	0.109*
H8B	0.9916	0.5206	0.6757	0.109*
H8C	0.8383	0.4430	0.5691	0.109*
C9	1.2863 (3)	0.8914 (3)	0.6646 (3)	0.0910 (11)
H9A	1.3491	0.8817	0.6214	0.136*
H9B	1.3336	0.8957	0.7368	0.136*
H9C	1.2740	0.9636	0.6764	0.136*
C10	0.5479 (3)	0.6799 (3)	0.2429 (2)	0.0612 (8)
C11	0.4522 (4)	0.5462 (3)	0.1642 (3)	0.0938 (12)
H11A	0.5166	0.5094	0.1406	0.141*
H11B	0.3757	0.5350	0.0986	0.141*
H11C	0.4044	0.5105	0.2041	0.141*
C12	0.6233 (4)	0.7418 (3)	0.1828 (3)	0.0872 (11)
H12A	0.6906	0.8233	0.2364	0.131*
H12B	0.5468	0.7395	0.1232	0.131*
H12C	0.6802	0.7017	0.1508	0.131*
C13	0.4474 (4)	0.7384 (3)	0.2846 (3)	0.0868 (11)
H13A	0.4019	0.7018	0.3249	0.130*
H13B	0.3690	0.7280	0.2207	0.130*
H13C	0.5081	0.8220	0.3345	0.130*
C14	0.5876 (3)	0.6876 (2)	0.4959 (2)	0.0434 (6)
C15	0.6381 (3)	0.7341 (2)	0.6202 (2)	0.0428 (6)
C16	0.5273 (3)	0.7074 (2)	0.6640 (2)	0.0580 (7)
H16	0.4250	0.6713	0.6169	0.070*
C17	0.5688 (4)	0.7342 (3)	0.7764 (3)	0.0723 (9)
H17	0.4938	0.7187	0.8054	0.087*
C18	0.7196 (5)	0.7836 (3)	0.8477 (3)	0.0749 (9)
C19	0.8284 (4)	0.8097 (3)	0.8031 (2)	0.0673 (8)
H19	0.9307	0.8435	0.8496	0.081*
C20	0.7883 (3)	0.7864 (2)	0.6908 (2)	0.0514 (7)
H20	0.8635	0.8062	0.6629	0.062*
C21	0.7651 (6)	0.8108 (4)	0.9712 (3)	0.1199 (16)
H21A	0.6959	0.7456	0.9765	0.144*
H21B	0.8661	0.8140	0.9981	0.144*
C22	0.7653 (7)	0.9205 (4)	1.0450 (3)	0.164 (3)
H22A	0.8261	0.9847	1.0354	0.246*
H22B	0.8069	0.9360	1.1226	0.246*
H22C	0.6631	0.9139	1.0264	0.246*
C23	0.7514 (3)	0.8794 (2)	0.5043 (2)	0.0421 (6)
C24	0.7141 (3)	0.9527 (2)	0.6002 (2)	0.0463 (6)
C25	0.8265 (3)	1.1102 (2)	0.7871 (2)	0.0478 (6)
C26	0.9177 (3)	1.2286 (2)	0.8324 (2)	0.0520 (7)
H26	0.9837	1.2555	0.8000	0.062*
C27	0.9094 (3)	1.3079 (2)	0.9280 (2)	0.0514 (7)
H27	0.9708	1.3891	0.9604	0.062*
C28	0.8115 (3)	1.2678 (2)	0.9753 (2)	0.0454 (6)
C29	0.7243 (3)	1.1468 (2)	0.9287 (2)	0.0579 (7)
H29	0.6599	1.1191	0.9617	0.069*
C30	0.7313 (3)	1.0667 (2)	0.8339 (2)	0.0597 (8)
H30	0.6727	0.9852	0.8026	0.072*
C31	0.7899 (3)	1.3503 (3)	1.0724 (2)	0.0538 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0611 (14)	0.0442 (12)	0.0336 (11)	0.0284 (11)	0.0231 (10)	0.0135 (10)
N2	0.0500 (12)	0.0365 (11)	0.0348 (11)	0.0227 (10)	0.0224 (9)	0.0136 (9)
O1	0.1187 (18)	0.0757 (15)	0.0599 (12)	0.0634 (14)	0.0559 (13)	0.0226 (11)
O2	0.0612 (12)	0.0487 (12)	0.0551 (12)	0.0063 (10)	0.0182 (10)	0.0151 (10)
O3	0.0763 (13)	0.0449 (11)	0.0692 (12)	0.0235 (10)	0.0470 (11)	0.0252 (10)
O4	0.0589 (13)	0.0656 (13)	0.0649 (12)	0.0355 (10)	0.0307 (10)	0.0168 (10)
O5	0.0550 (11)	0.0421 (10)	0.0556 (11)	0.0202 (9)	0.0290 (10)	0.0033 (9)
O6	0.1091 (17)	0.0500 (13)	0.0685 (14)	0.0383 (12)	0.0587 (13)	0.0172 (11)
O7	0.1077 (17)	0.0750 (15)	0.0770 (14)	0.0347 (13)	0.0672 (14)	0.0262 (12)
C1	0.0710 (18)	0.0383 (15)	0.0491 (16)	0.0295 (14)	0.0353 (15)	0.0157 (13)
C2	0.0547 (16)	0.0388 (15)	0.0552 (16)	0.0290 (13)	0.0329 (14)	0.0193 (13)
C3	0.0500 (16)	0.0381 (15)	0.0635 (17)	0.0232 (12)	0.0251 (14)	0.0184 (13)
C4	0.0528 (17)	0.0518 (17)	0.0691 (19)	0.0317 (15)	0.0307 (15)	0.0318 (15)
C5	0.0485 (17)	0.0611 (19)	0.0695 (19)	0.0300 (15)	0.0209 (15)	0.0270 (16)
C6	0.0472 (17)	0.0495 (17)	0.083 (2)	0.0249 (14)	0.0304 (16)	0.0247 (16)
C7	0.0607 (18)	0.0436 (16)	0.077 (2)	0.0299 (14)	0.0418 (17)	0.0296 (15)
C8	0.073 (2)	0.079 (2)	0.089 (2)	0.0394 (18)	0.0335 (18)	0.0522 (19)
C9	0.0531 (19)	0.071 (2)	0.126 (3)	0.0163 (17)	0.026 (2)	0.036 (2)
C10	0.077 (2)	0.0640 (19)	0.0407 (15)	0.0340 (16)	0.0176 (15)	0.0221 (15)
C11	0.100 (3)	0.080 (3)	0.0520 (19)	0.021 (2)	−0.0005 (18)	0.0133 (18)
C12	0.126 (3)	0.100 (3)	0.063 (2)	0.059 (2)	0.044 (2)	0.052 (2)
C13	0.089 (2)	0.124 (3)	0.066 (2)	0.069 (2)	0.0233 (18)	0.046 (2)
C14	0.0444 (15)	0.0381 (15)	0.0481 (15)	0.0183 (13)	0.0208 (13)	0.0176 (13)
C15	0.0507 (16)	0.0375 (14)	0.0460 (14)	0.0203 (12)	0.0246 (13)	0.0201 (12)
C16	0.0671 (18)	0.0496 (17)	0.0667 (19)	0.0219 (14)	0.0399 (16)	0.0295 (15)
C17	0.102 (3)	0.069 (2)	0.078 (2)	0.040 (2)	0.064 (2)	0.0442 (18)
C18	0.119 (3)	0.074 (2)	0.0559 (19)	0.052 (2)	0.046 (2)	0.0382 (18)
C19	0.077 (2)	0.076 (2)	0.0479 (17)	0.0398 (17)	0.0195 (15)	0.0250 (16)
C20	0.0588 (18)	0.0534 (16)	0.0463 (15)	0.0283 (14)	0.0249 (14)	0.0205 (13)
C21	0.194 (5)	0.136 (4)	0.064 (2)	0.085 (4)	0.066 (3)	0.057 (3)
C22	0.285 (7)	0.099 (4)	0.065 (3)	0.039 (4)	0.068 (4)	0.028 (3)
C23	0.0468 (15)	0.0378 (15)	0.0461 (14)	0.0219 (12)	0.0241 (12)	0.0166 (12)
C24	0.0549 (17)	0.0381 (15)	0.0534 (16)	0.0247 (13)	0.0300 (15)	0.0187 (13)
C25	0.0566 (16)	0.0387 (15)	0.0483 (15)	0.0245 (13)	0.0284 (13)	0.0117 (13)
C26	0.0586 (17)	0.0433 (16)	0.0557 (16)	0.0217 (13)	0.0339 (14)	0.0168 (13)
C27	0.0593 (17)	0.0357 (14)	0.0525 (16)	0.0182 (13)	0.0290 (14)	0.0103 (13)
C28	0.0564 (16)	0.0447 (15)	0.0407 (14)	0.0273 (13)	0.0235 (12)	0.0175 (12)
C29	0.075 (2)	0.0483 (17)	0.0595 (17)	0.0269 (15)	0.0420 (16)	0.0236 (14)
C30	0.076 (2)	0.0351 (15)	0.0654 (18)	0.0192 (14)	0.0402 (16)	0.0161 (14)
C31	0.0663 (18)	0.0540 (18)	0.0460 (15)	0.0306 (15)	0.0278 (15)	0.0198 (14)

Geometric parameters (Å, º)

N1—C1	1.354 (3)	C11—H11C	0.96
N1—N2	1.399 (2)	C12—H12A	0.96
N1—C10	1.510 (3)	C12—H12B	0.96
N2—C23	1.388 (3)	C12—H12C	0.96
N2—C14	1.430 (3)	C13—H13A	0.96
O1—C1	1.231 (3)	C13—H13B	0.96
O2—C14	1.200 (3)	C13—H13C	0.96
O3—C23	1.200 (3)	C14—C15	1.473 (3)
O4—C24	1.186 (3)	C15—C20	1.371 (4)
O5—C24	1.338 (3)	C15—C16	1.391 (3)
O5—C25	1.413 (3)	C16—C17	1.368 (4)
O6—C31	1.316 (3)	C16—H16	0.93
O6—H6	0.82	C17—C18	1.381 (5)
O7—C31	1.194 (3)	C17—H17	0.93
C1—C2	1.488 (4)	C18—C19	1.381 (4)
C2—C7	1.380 (4)	C18—C21	1.512 (4)
C2—C3	1.387 (3)	C19—C20	1.380 (4)
C3—C4	1.384 (4)	C19—H19	0.93
C3—H3	0.93	C20—H20	0.93
C4—C5	1.383 (4)	C21—C22	1.437 (6)
C4—C8	1.501 (4)	C21—H21A	0.97
C5—C6	1.385 (4)	C21—H21B	0.97
C5—H5	0.93	C22—H22A	0.96
C6—C7	1.384 (4)	C22—H22B	0.96
C6—C9	1.511 (4)	C22—H22C	0.96
C7—H7	0.93	C23—C24	1.523 (3)
C8—H8A	0.96	C25—C26	1.364 (3)
C8—H8B	0.96	C25—C30	1.366 (3)
C8—H8C	0.96	C26—C27	1.388 (3)
C9—H9A	0.96	C26—H26	0.93
C9—H9B	0.96	C27—C28	1.374 (3)
C9—H9C	0.96	C27—H27	0.93
C10—C12	1.523 (4)	C28—C29	1.380 (4)
C10—C13	1.529 (4)	C28—C31	1.493 (3)
C10—C11	1.531 (4)	C29—C30	1.379 (4)
C11—H11A	0.96	C29—H29	0.93
C11—H11B	0.96	C30—H30	0.93
C1—N1—N2	115.95 (19)	H13A—C13—H13C	109.5
C1—N1—C10	124.2 (2)	H13B—C13—H13C	109.5
N2—N1—C10	119.57 (19)	O2—C14—N2	118.7 (2)
C23—N2—N1	115.76 (18)	O2—C14—C15	123.4 (2)
C23—N2—C14	127.29 (19)	N2—C14—C15	117.7 (2)
N1—N2—C14	116.67 (19)	C20—C15—C16	119.0 (2)
C24—O5—C25	117.80 (19)	C20—C15—C14	122.7 (2)
C31—O6—H6	109.5	C16—C15—C14	117.5 (2)
O1—C1—N1	120.5 (3)	C17—C16—C15	120.0 (3)
O1—C1—C2	121.6 (2)	C17—C16—H16	120.0
N1—C1—C2	117.9 (2)	C15—C16—H16	120.0
C7—C2—C3	119.6 (3)	C16—C17—C18	121.5 (3)
C7—C2—C1	120.5 (2)	C16—C17—H17	119.2
C3—C2—C1	119.8 (2)	C18—C17—H17	119.2
C4—C3—C2	120.9 (3)	C17—C18—C19	117.8 (3)
C4—C3—H3	119.5	C17—C18—C21	121.5 (3)
C2—C3—H3	119.5	C19—C18—C21	120.7 (4)
C5—C4—C3	118.1 (3)	C20—C19—C18	121.3 (3)
C5—C4—C8	121.2 (3)	C20—C19—H19	119.4
C3—C4—C8	120.7 (3)	C18—C19—H19	119.4
C4—C5—C6	122.2 (3)	C15—C20—C19	120.2 (3)
C4—C5—H5	118.9	C15—C20—H20	119.9
C6—C5—H5	118.9	C19—C20—H20	119.9
C7—C6—C5	118.3 (3)	C22—C21—C18	114.6 (4)
C7—C6—C9	121.2 (3)	C22—C21—H21A	108.6
C5—C6—C9	120.5 (3)	C18—C21—H21A	108.6
C2—C7—C6	120.8 (3)	C22—C21—H21B	108.6
C2—C7—H7	119.6	C18—C21—H21B	108.6
C6—C7—H7	119.6	H21A—C21—H21B	107.6
C4—C8—H8A	109.5	C21—C22—H22A	109.5
C4—C8—H8B	109.5	C21—C22—H22B	109.5
H8A—C8—H8B	109.5	H22A—C22—H22B	109.5
C4—C8—H8C	109.5	C21—C22—H22C	109.5
H8A—C8—H8C	109.5	H22A—C22—H22C	109.5
H8B—C8—H8C	109.5	H22B—C22—H22C	109.5
C6—C9—H9A	109.5	O3—C23—N2	122.9 (2)
C6—C9—H9B	109.5	O3—C23—C24	119.2 (2)
H9A—C9—H9B	109.5	N2—C23—C24	117.3 (2)
C6—C9—H9C	109.5	O4—C24—O5	127.3 (2)
H9A—C9—H9C	109.5	O4—C24—C23	121.6 (2)
H9B—C9—H9C	109.5	O5—C24—C23	110.7 (2)
N1—C10—C12	109.9 (2)	C26—C25—C30	122.7 (2)
N1—C10—C13	108.8 (2)	C26—C25—O5	116.5 (2)
C12—C10—C13	108.7 (3)	C30—C25—O5	120.7 (2)
N1—C10—C11	107.8 (2)	C25—C26—C27	118.2 (2)
C12—C10—C11	111.7 (3)	C25—C26—H26	120.9
C13—C10—C11	109.8 (3)	C27—C26—H26	120.9
C10—C11—H11A	109.5	C28—C27—C26	120.6 (2)
C10—C11—H11B	109.5	C28—C27—H27	119.7
H11A—C11—H11B	109.5	C26—C27—H27	119.7
C10—C11—H11C	109.5	C27—C28—C29	119.3 (2)
H11A—C11—H11C	109.5	C27—C28—C31	122.5 (2)
H11B—C11—H11C	109.5	C29—C28—C31	118.1 (2)
C10—C12—H12A	109.5	C30—C29—C28	120.8 (2)
C10—C12—H12B	109.5	C30—C29—H29	119.6
H12A—C12—H12B	109.5	C28—C29—H29	119.6
C10—C12—H12C	109.5	C25—C30—C29	118.2 (2)
H12A—C12—H12C	109.5	C25—C30—H30	120.9
H12B—C12—H12C	109.5	C29—C30—H30	120.9
C10—C13—H13A	109.5	O7—C31—O6	123.6 (2)
C10—C13—H13B	109.5	O7—C31—C28	123.1 (3)
H13A—C13—H13B	109.5	O6—C31—C28	113.3 (2)
C10—C13—H13C	109.5
C1—N1—N2—C23	91.1 (2)	C20—C15—C16—C17	0.6 (4)
C10—N1—N2—C23	−83.4 (3)	C14—C15—C16—C17	171.2 (2)
C1—N1—N2—C14	−94.5 (2)	C15—C16—C17—C18	−2.5 (5)
C10—N1—N2—C14	91.0 (3)	C16—C17—C18—C19	2.4 (5)
N2—N1—C1—O1	−173.1 (2)	C16—C17—C18—C21	−178.7 (3)
C10—N1—C1—O1	1.1 (4)	C17—C18—C19—C20	−0.4 (5)
N2—N1—C1—C2	6.9 (3)	C21—C18—C19—C20	−179.4 (3)
C10—N1—C1—C2	−178.9 (2)	C16—C15—C20—C19	1.3 (4)
O1—C1—C2—C7	79.7 (3)	C14—C15—C20—C19	−168.7 (2)
N1—C1—C2—C7	−100.3 (3)	C18—C19—C20—C15	−1.4 (4)
O1—C1—C2—C3	−98.1 (3)	C17—C18—C21—C22	−80.8 (6)
N1—C1—C2—C3	81.8 (3)	C19—C18—C21—C22	98.1 (5)
C7—C2—C3—C4	0.6 (4)	N1—N2—C23—O3	−12.8 (3)
C1—C2—C3—C4	178.5 (2)	C14—N2—C23—O3	173.6 (2)
C2—C3—C4—C5	−0.8 (4)	N1—N2—C23—C24	158.2 (2)
C2—C3—C4—C8	176.9 (2)	C14—N2—C23—C24	−15.4 (3)
C3—C4—C5—C6	0.7 (4)	C25—O5—C24—O4	5.2 (4)
C8—C4—C5—C6	−177.0 (3)	C25—O5—C24—C23	177.9 (2)
C4—C5—C6—C7	−0.4 (4)	O3—C23—C24—O4	113.8 (3)
C4—C5—C6—C9	178.7 (3)	N2—C23—C24—O4	−57.5 (3)
C3—C2—C7—C6	−0.3 (4)	O3—C23—C24—O5	−59.4 (3)
C1—C2—C7—C6	−178.2 (2)	N2—C23—C24—O5	129.3 (2)
C5—C6—C7—C2	0.2 (4)	C24—O5—C25—C26	−130.1 (3)
C9—C6—C7—C2	−178.9 (3)	C24—O5—C25—C30	53.4 (3)
C1—N1—C10—C12	−56.9 (3)	C30—C25—C26—C27	−1.9 (4)
N2—N1—C10—C12	117.1 (3)	O5—C25—C26—C27	−178.4 (2)
C1—N1—C10—C13	−175.9 (3)	C25—C26—C27—C28	−0.1 (4)
N2—N1—C10—C13	−1.9 (3)	C26—C27—C28—C29	1.9 (4)
C1—N1—C10—C11	65.0 (3)	C26—C27—C28—C31	−175.1 (2)
N2—N1—C10—C11	−121.0 (3)	C27—C28—C29—C30	−1.8 (4)
C23—N2—C14—O2	152.9 (2)	C31—C28—C29—C30	175.4 (3)
N1—N2—C14—O2	−20.7 (3)	C26—C25—C30—C29	2.1 (4)
C23—N2—C14—C15	−32.0 (3)	O5—C25—C30—C29	178.5 (3)
N1—N2—C14—C15	154.4 (2)	C28—C29—C30—C25	−0.2 (4)
O2—C14—C15—C20	134.2 (3)	C27—C28—C31—O7	−178.9 (3)
N2—C14—C15—C20	−40.7 (3)	C29—C28—C31—O7	4.0 (4)
O2—C14—C15—C16	−36.0 (4)	C27—C28—C31—O6	1.8 (4)
N2—C14—C15—C16	149.1 (2)	C29—C28—C31—O6	−175.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O1^i	0.82	1.86	2.655 (2)	163
C9—H9A···O4^ii	0.96	2.50	3.393 (4)	154
C11—H11A···O1	0.96	2.46	3.052 (5)	120
C12—H12C···O1	0.96	2.36	2.937 (5)	118
C13—H13A···O2	0.96	2.55	3.261 (5)	131
C17—H17···O7^iii	0.93	2.49	3.422 (5)	178
C13—H13B···Cg3^iv	0.96	2.80	3.670 (4)	151
C20—H20···Cg1	0.93	2.64	3.365 (3)	136
C30—H30···Cg2	0.93	2.82	3.618 (3)	145

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