Dimethyl 3-(methyl­amino)-2-(4-methyl­phen­yl)furan-4,5-dicarboxyl­ate

The title compound, C₁₆H₁₇NO₅, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the furan and benzene rings are 26.38 (13) and 28.52 (14)°. The mol­ecules are linked by N—H...O hydrogen bonds, leading to dimers.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.159
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H201   ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H201   ..  O2      ..       2.64 Ang.

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

Dimethyl 3-(methylamino)-2-(4-methylphenyl)furan-4,5-dicarboxylate

Crystal data

C16H17NO5	F(000) = 1280.00
Mr = 303.31	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 12870 reflections
a = 15.5390 (2) Å	θ = 1.8–27.5°
b = 17.8363 (3) Å	µ = 0.10 mm^−1
c = 11.6349 (3) Å	T = 295 K
β = 108.6580 (7)°	Prism, yellow
V = 3055.23 (10) Å^3	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	3442 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.050
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.943, Tmax = 0.990	k = −23→23
28950 measured reflections	l = −15→14
6994 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[0.0014Fo^2 + 1σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.159	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.57 e Å^−3
6992 reflections	Δρmin = −0.59 e Å^−3
397 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.19334 (11)	0.55133 (9)	0.60462 (14)	0.0438 (5)
O2	0.13246 (12)	0.30854 (10)	0.47869 (17)	0.0586 (6)
O3	0.12175 (12)	0.33308 (9)	0.66288 (14)	0.0487 (5)
O4	0.00263 (12)	0.46164 (11)	0.64034 (18)	0.0569 (6)
O5	0.07660 (12)	0.56647 (10)	0.72350 (17)	0.0579 (6)
O6	0.32307 (11)	0.51294 (9)	0.92235 (16)	0.0467 (5)
O7	0.29690 (12)	0.25939 (10)	0.90574 (17)	0.0573 (6)
O8	0.33441 (12)	0.30705 (10)	0.75115 (16)	0.0511 (5)
O9	0.48171 (12)	0.41124 (11)	0.8276 (2)	0.0645 (6)
O10	0.44858 (12)	0.53331 (10)	0.82024 (18)	0.0605 (6)
N1	0.28585 (13)	0.40982 (12)	0.45587 (19)	0.0467 (6)
N2	0.17956 (12)	0.36918 (12)	0.97855 (19)	0.0436 (6)
C1	0.25200 (17)	0.52907 (13)	0.5430 (2)	0.0422 (7)
C2	0.24027 (16)	0.45424 (12)	0.5171 (2)	0.0390 (7)
C3	0.17029 (16)	0.42928 (12)	0.5638 (2)	0.0380 (6)
C4	0.14308 (16)	0.49067 (13)	0.6136 (2)	0.0409 (7)
C5	0.30801 (17)	0.58925 (12)	0.5188 (2)	0.0408 (7)
C6	0.32681 (19)	0.65345 (14)	0.5906 (2)	0.0514 (8)
C7	0.37400 (18)	0.71244 (14)	0.5623 (2)	0.0538 (8)
C8	0.40382 (17)	0.71026 (14)	0.4619 (2)	0.0493 (8)
C9	0.4521 (2)	0.77634 (17)	0.4303 (3)	0.0743 (11)
C10	0.38659 (18)	0.64553 (17)	0.3920 (2)	0.0538 (8)
C11	0.33968 (17)	0.58587 (14)	0.4190 (2)	0.0468 (7)
C12	0.13875 (16)	0.35145 (13)	0.5616 (2)	0.0412 (7)
C13	0.0852 (2)	0.25869 (14)	0.6658 (2)	0.0632 (10)
C14	0.06647 (19)	0.50340 (13)	0.6596 (2)	0.0433 (7)
C15	0.0045 (2)	0.58471 (18)	0.7720 (2)	0.0681 (10)
C16	0.38497 (18)	0.40661 (16)	0.5051 (2)	0.0575 (9)
C17	0.25543 (16)	0.48947 (13)	0.9677 (2)	0.0422 (7)
C18	0.24219 (16)	0.41455 (13)	0.9491 (2)	0.0390 (7)
C19	0.30580 (16)	0.39020 (12)	0.8905 (2)	0.0380 (6)
C20	0.35412 (16)	0.45188 (13)	0.8787 (2)	0.0404 (7)
C21	0.21895 (17)	0.54724 (14)	1.0280 (2)	0.0458 (7)
C22	0.2190 (2)	0.62213 (16)	0.9966 (2)	0.0616 (9)
C23	0.1877 (2)	0.67608 (18)	1.0574 (3)	0.0771 (11)
C24	0.1560 (2)	0.6579 (2)	1.1527 (3)	0.0749 (11)
C25	0.1273 (2)	0.7183 (2)	1.2243 (4)	0.1187 (17)
C26	0.15381 (19)	0.5835 (2)	1.1813 (2)	0.0670 (10)
C27	0.18474 (18)	0.52863 (17)	1.1206 (2)	0.0547 (8)
C28	0.31275 (16)	0.31266 (13)	0.8525 (2)	0.0392 (7)
C29	0.3510 (2)	0.23199 (16)	0.7162 (2)	0.0672 (10)
C30	0.43449 (18)	0.46157 (14)	0.8395 (2)	0.0433 (7)
C31	0.5268 (2)	0.54973 (19)	0.7831 (3)	0.0737 (11)
C32	0.08478 (17)	0.39031 (16)	0.9368 (2)	0.0526 (8)
H6	0.3073	0.6568	0.6581	0.064*
H7	0.3863	0.7547	0.6118	0.065*
H10	0.4066	0.6424	0.3249	0.066*
H11	0.3298	0.5429	0.3713	0.056*
H22	0.2401	0.6361	0.9333	0.077*
H23	0.1882	0.7260	1.0347	0.094*
H26	0.1311	0.5698	1.2433	0.081*
H27	0.1828	0.4786	1.1422	0.065*
H91	0.4085	0.8093	0.3769	0.090*
H92	0.4940	0.7589	0.3908	0.090*
H93	0.4848	0.8029	0.5030	0.090*
H101	0.2611	0.3661	0.4424	0.059*
H131	0.0201	0.2604	0.6346	0.083*
H132	0.1039	0.2408	0.7479	0.083*
H133	0.1075	0.2255	0.6169	0.083*
H151	−0.0400	0.6148	0.7142	0.088*
H152	0.0288	0.6122	0.8464	0.088*
H153	−0.0234	0.5394	0.7873	0.088*
H161	0.4108	0.4455	0.4694	0.073*
H162	0.4055	0.3587	0.4868	0.073*
H163	0.4036	0.4134	0.5914	0.074*
H201	0.1970	0.3294	1.0214	0.055*
H251	0.1788	0.7333	1.2915	0.147*
H252	0.0808	0.6990	1.2540	0.147*
H253	0.1043	0.7608	1.1730	0.147*
H291	0.4142	0.2201	0.7521	0.086*
H292	0.3348	0.2292	0.6295	0.086*
H293	0.3151	0.1969	0.7439	0.086*
H311	0.5792	0.5583	0.8529	0.095*
H312	0.5147	0.5937	0.7329	0.095*
H313	0.5381	0.5080	0.7378	0.095*
H321	0.0479	0.3460	0.9251	0.066*
H322	0.0717	0.4169	0.8614	0.066*
H323	0.0718	0.4220	0.9960	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0489 (10)	0.0333 (9)	0.0549 (11)	0.0010 (8)	0.0247 (9)	−0.0013 (8)
O2	0.0809 (14)	0.0455 (11)	0.0589 (12)	−0.0111 (10)	0.0357 (11)	−0.0128 (9)
O3	0.0648 (11)	0.0376 (10)	0.0498 (10)	−0.0075 (8)	0.0271 (10)	−0.0016 (8)
O4	0.0491 (11)	0.0573 (12)	0.0698 (13)	−0.0022 (10)	0.0268 (10)	0.0008 (10)
O5	0.0655 (12)	0.0467 (11)	0.0734 (13)	0.0047 (9)	0.0391 (11)	−0.0101 (9)
O6	0.0480 (10)	0.0392 (10)	0.0584 (11)	−0.0053 (8)	0.0245 (9)	−0.0060 (8)
O7	0.0815 (14)	0.0376 (10)	0.0661 (13)	0.0057 (9)	0.0421 (11)	0.0098 (9)
O8	0.0686 (12)	0.0441 (10)	0.0496 (11)	0.0034 (9)	0.0316 (10)	−0.0016 (8)
O9	0.0594 (12)	0.0562 (12)	0.0913 (15)	0.0065 (10)	0.0429 (12)	0.0021 (11)
O10	0.0605 (12)	0.0455 (11)	0.0899 (15)	−0.0079 (9)	0.0441 (12)	0.0021 (10)
N1	0.0507 (13)	0.0400 (12)	0.0562 (13)	−0.0023 (10)	0.0264 (11)	−0.0090 (10)
N2	0.0425 (12)	0.0425 (12)	0.0503 (12)	0.0021 (10)	0.0210 (11)	0.0127 (10)
C1	0.0448 (14)	0.0386 (14)	0.0472 (15)	0.0020 (11)	0.0206 (13)	0.0000 (11)
C2	0.0418 (13)	0.0356 (14)	0.0414 (14)	0.0014 (11)	0.0159 (12)	−0.0003 (11)
C3	0.0416 (13)	0.0345 (13)	0.0390 (14)	0.0018 (11)	0.0143 (12)	0.0017 (11)
C4	0.0423 (14)	0.0362 (14)	0.0466 (14)	0.0002 (11)	0.0176 (12)	0.0038 (11)
C5	0.0411 (14)	0.0343 (13)	0.0477 (15)	0.0039 (11)	0.0155 (12)	0.0028 (11)
C6	0.0594 (17)	0.0444 (16)	0.0557 (17)	−0.0018 (13)	0.0258 (14)	−0.0044 (13)
C7	0.0588 (17)	0.0376 (15)	0.0661 (19)	−0.0047 (13)	0.0214 (16)	−0.0012 (13)
C8	0.0400 (14)	0.0438 (16)	0.0613 (18)	−0.0004 (12)	0.0124 (14)	0.0090 (13)
C9	0.072 (2)	0.064 (2)	0.087 (2)	−0.0183 (17)	0.026 (2)	0.0118 (18)
C10	0.0526 (16)	0.0601 (18)	0.0526 (17)	−0.0016 (14)	0.0222 (14)	0.0067 (14)
C11	0.0505 (15)	0.0423 (15)	0.0486 (16)	−0.0049 (12)	0.0172 (13)	−0.0005 (12)
C12	0.0402 (14)	0.0381 (14)	0.0469 (15)	0.0040 (11)	0.0162 (12)	−0.0007 (12)
C13	0.086 (2)	0.0407 (16)	0.079 (2)	−0.0155 (15)	0.0489 (19)	−0.0015 (14)
C14	0.0499 (15)	0.0385 (14)	0.0448 (14)	0.0102 (13)	0.0199 (13)	0.0075 (12)
C15	0.076 (2)	0.065 (2)	0.079 (2)	0.0221 (17)	0.0459 (19)	−0.0007 (16)
C16	0.0568 (17)	0.0525 (17)	0.072 (2)	0.0052 (14)	0.0338 (16)	−0.0046 (14)
C17	0.0389 (13)	0.0456 (15)	0.0465 (15)	−0.0020 (11)	0.0196 (12)	−0.0010 (12)
C18	0.0403 (13)	0.0399 (14)	0.0383 (14)	0.0015 (11)	0.0145 (12)	0.0015 (11)
C19	0.0397 (14)	0.0385 (14)	0.0380 (13)	0.0010 (11)	0.0158 (11)	0.0011 (11)
C20	0.0441 (14)	0.0357 (14)	0.0432 (14)	0.0018 (11)	0.0164 (12)	−0.0018 (11)
C21	0.0404 (14)	0.0451 (16)	0.0523 (16)	−0.0031 (12)	0.0156 (13)	−0.0128 (12)
C22	0.0603 (18)	0.0493 (18)	0.083 (2)	−0.0054 (14)	0.0335 (17)	−0.0135 (15)
C23	0.064 (2)	0.0458 (19)	0.126 (3)	−0.0053 (15)	0.037 (2)	−0.0276 (19)
C24	0.0446 (17)	0.082 (2)	0.098 (2)	−0.0086 (17)	0.0240 (18)	−0.049 (2)
C25	0.086 (2)	0.114 (3)	0.166 (4)	−0.014 (2)	0.055 (3)	−0.090 (3)
C26	0.0468 (17)	0.093 (2)	0.064 (2)	−0.0045 (17)	0.0222 (15)	−0.0266 (18)
C27	0.0476 (15)	0.0644 (19)	0.0523 (16)	−0.0006 (14)	0.0163 (14)	−0.0114 (14)
C28	0.0386 (13)	0.0412 (15)	0.0393 (14)	0.0027 (11)	0.0147 (12)	0.0020 (11)
C29	0.089 (2)	0.0556 (19)	0.070 (2)	0.0118 (17)	0.0428 (19)	−0.0110 (15)
C30	0.0446 (15)	0.0434 (15)	0.0440 (15)	−0.0046 (13)	0.0170 (13)	−0.0006 (12)
C31	0.066 (2)	0.068 (2)	0.102 (2)	−0.0185 (17)	0.048 (2)	0.0042 (18)
C32	0.0459 (16)	0.0559 (17)	0.0611 (18)	−0.0033 (13)	0.0242 (14)	0.0049 (14)

Geometric parameters (Å, º)

O1—C1	1.386 (3)	C21—C27	1.385 (4)
O1—C4	1.358 (3)	C22—C23	1.373 (5)
O2—C12	1.211 (3)	C23—C24	1.388 (5)
O3—C12	1.328 (3)	C24—C25	1.513 (6)
O3—C13	1.448 (3)	C24—C26	1.371 (5)
O4—C14	1.203 (3)	C26—C27	1.381 (4)
O5—C14	1.329 (3)	N1—H101	0.862
O5—C15	1.444 (4)	N2—H201	0.860
O6—C17	1.383 (3)	C6—H6	0.930
O6—C20	1.354 (3)	C7—H7	0.930
O7—C28	1.202 (3)	C9—H91	0.960
O8—C28	1.329 (3)	C9—H92	0.960
O8—C29	1.446 (3)	C9—H93	0.960
O9—C30	1.195 (3)	C10—H10	0.930
O10—C30	1.329 (3)	C11—H11	0.930
O10—C31	1.445 (4)	C13—H131	0.960
N1—C2	1.400 (3)	C13—H132	0.960
N1—C16	1.463 (3)	C13—H133	0.960
N2—C18	1.390 (3)	C15—H151	0.960
N2—C32	1.445 (3)	C15—H152	0.960
C1—C2	1.368 (3)	C15—H153	0.960
C1—C5	1.465 (3)	C16—H161	0.960
C2—C3	1.434 (3)	C16—H162	0.960
C3—C4	1.368 (3)	C16—H163	0.960
C3—C12	1.470 (3)	C22—H22	0.930
C4—C14	1.471 (4)	C23—H23	0.930
C5—C6	1.392 (3)	C25—H251	0.960
C5—C11	1.400 (4)	C25—H252	0.960
C6—C7	1.381 (4)	C25—H253	0.960
C7—C8	1.389 (4)	C26—H26	0.930
C8—C9	1.505 (4)	C27—H27	0.930
C8—C10	1.388 (4)	C29—H291	0.960
C10—C11	1.381 (4)	C29—H292	0.960
C17—C18	1.359 (3)	C29—H293	0.960
C17—C21	1.460 (3)	C31—H311	0.960
C18—C19	1.436 (3)	C31—H312	0.960
C19—C20	1.363 (3)	C31—H313	0.960
C19—C28	1.467 (3)	C32—H321	0.960
C20—C30	1.471 (4)	C32—H322	0.960
C21—C22	1.385 (3)	C32—H323	0.960
C1—O1—C4	107.54 (19)	C18—N2—H201	120.5
C12—O3—C13	115.9 (2)	C32—N2—H201	120.6
C14—O5—C15	116.2 (2)	C5—C6—H6	119.7
C17—O6—C20	107.76 (19)	C7—C6—H6	119.6
C28—O8—C29	115.9 (2)	C6—C7—H7	119.2
C30—O10—C31	116.4 (2)	C8—C7—H7	119.1
C2—N1—C16	117.6 (2)	C8—C9—H91	109.5
C18—N2—C32	118.9 (2)	C8—C9—H92	109.3
O1—C1—C2	109.3 (2)	C8—C9—H93	109.6
O1—C1—C5	114.8 (2)	H91—C9—H92	109.5
C2—C1—C5	135.9 (2)	H91—C9—H93	109.5
N1—C2—C1	127.7 (2)	H92—C9—H93	109.5
N1—C2—C3	125.9 (2)	C8—C10—H10	119.2
C1—C2—C3	106.4 (2)	C11—C10—H10	119.1
C2—C3—C4	106.7 (2)	C5—C11—H11	119.7
C2—C3—C12	125.2 (2)	C10—C11—H11	119.9
C4—C3—C12	128.1 (2)	O3—C13—H131	109.7
O1—C4—C3	110.0 (2)	O3—C13—H132	109.3
O1—C4—C14	117.2 (2)	O3—C13—H133	109.4
C3—C4—C14	132.4 (2)	H131—C13—H132	109.5
C1—C5—C6	120.8 (2)	H131—C13—H133	109.5
C1—C5—C11	121.0 (2)	H132—C13—H133	109.5
C6—C5—C11	118.1 (2)	O5—C15—H151	109.2
C5—C6—C7	120.6 (2)	O5—C15—H152	109.7
C6—C7—C8	121.7 (2)	O5—C15—H153	109.6
C7—C8—C9	120.7 (2)	H151—C15—H152	109.5
C7—C8—C10	117.5 (2)	H151—C15—H153	109.5
C9—C8—C10	121.8 (3)	H152—C15—H153	109.5
C8—C10—C11	121.7 (2)	N1—C16—H161	109.7
C5—C11—C10	120.4 (2)	N1—C16—H162	109.3
O2—C12—O3	124.2 (2)	N1—C16—H163	109.4
O2—C12—C3	123.5 (2)	H161—C16—H162	109.5
O3—C12—C3	112.2 (2)	H161—C16—H163	109.5
O4—C14—O5	124.9 (2)	H162—C16—H163	109.5
O4—C14—C4	123.5 (2)	C21—C22—H22	119.8
O5—C14—C4	111.7 (2)	C23—C22—H22	119.6
O6—C17—C18	109.4 (2)	C22—C23—H23	119.3
O6—C17—C21	115.4 (2)	C24—C23—H23	119.1
C18—C17—C21	135.1 (2)	C24—C25—H251	109.4
N2—C18—C17	128.0 (2)	C24—C25—H252	109.3
N2—C18—C19	125.7 (2)	C24—C25—H253	109.7
C17—C18—C19	106.3 (2)	H251—C25—H252	109.5
C18—C19—C20	106.8 (2)	H251—C25—H253	109.5
C18—C19—C28	123.8 (2)	H252—C25—H253	109.5
C20—C19—C28	129.4 (2)	C24—C26—H26	119.2
O6—C20—C19	109.7 (2)	C27—C26—H26	119.3
O6—C20—C30	117.5 (2)	C21—C27—H27	119.6
C19—C20—C30	132.5 (2)	C26—C27—H27	119.7
C17—C21—C22	121.3 (2)	O8—C29—H291	109.4
C17—C21—C27	120.6 (2)	O8—C29—H292	109.5
C22—C21—C27	118.0 (2)	O8—C29—H293	109.6
C21—C22—C23	120.6 (3)	H291—C29—H292	109.5
C22—C23—C24	121.6 (3)	H291—C29—H293	109.5
C23—C24—C25	121.1 (3)	H292—C29—H293	109.5
C23—C24—C26	117.6 (3)	O10—C31—H311	110.2
C25—C24—C26	121.3 (3)	O10—C31—H312	109.1
C24—C26—C27	121.5 (3)	O10—C31—H313	109.0
C21—C27—C26	120.7 (2)	H311—C31—H312	109.5
O7—C28—O8	123.3 (2)	H311—C31—H313	109.5
O7—C28—C19	122.9 (2)	H312—C31—H313	109.5
O8—C28—C19	113.7 (2)	N2—C32—H321	109.4
O9—C30—O10	124.3 (2)	N2—C32—H322	109.3
O9—C30—C20	124.1 (2)	N2—C32—H323	109.8
O10—C30—C20	111.6 (2)	H321—C32—H322	109.5
C2—N1—H101	109.6	H321—C32—H323	109.5
C16—N1—H101	112.9	H322—C32—H323	109.5
C1—O1—C4—C3	2.4 (2)	C1—C5—C6—C7	−175.2 (2)
C1—O1—C4—C14	−171.06 (18)	C1—C5—C11—C10	175.1 (2)
C4—O1—C1—C2	−1.9 (2)	C6—C5—C11—C10	−1.3 (3)
C4—O1—C1—C5	176.56 (18)	C11—C5—C6—C7	1.1 (3)
C13—O3—C12—O2	−6.1 (3)	C5—C6—C7—C8	0.4 (3)
C13—O3—C12—C3	176.5 (2)	C6—C7—C8—C9	177.8 (2)
C15—O5—C14—O4	−0.0 (2)	C6—C7—C8—C10	−1.7 (3)
C15—O5—C14—C4	179.4 (2)	C7—C8—C10—C11	1.5 (3)
C17—O6—C20—C19	2.3 (2)	C9—C8—C10—C11	−177.9 (2)
C17—O6—C20—C30	−172.52 (18)	C8—C10—C11—C5	−0.1 (2)
C20—O6—C17—C18	−1.9 (2)	O6—C17—C18—N2	−178.60 (19)
C20—O6—C17—C21	175.10 (18)	O6—C17—C18—C19	0.7 (2)
C29—O8—C28—O7	−8.6 (3)	O6—C17—C21—C22	28.0 (3)
C29—O8—C28—C19	174.1 (2)	O6—C17—C21—C27	−150.7 (2)
C31—O10—C30—O9	−0.2 (3)	C18—C17—C21—C22	−156.0 (2)
C31—O10—C30—C20	179.0 (2)	C18—C17—C21—C27	25.3 (3)
C16—N1—C2—C1	57.1 (3)	C21—C17—C18—N2	5.2 (4)
C16—N1—C2—C3	−123.8 (2)	C21—C17—C18—C19	−175.4 (2)
C32—N2—C18—C17	53.0 (3)	N2—C18—C19—C20	−180.0 (2)
C32—N2—C18—C19	−126.2 (2)	N2—C18—C19—C28	0.4 (3)
O1—C1—C2—N1	179.92 (19)	C17—C18—C19—C20	0.7 (2)
O1—C1—C2—C3	0.6 (2)	C17—C18—C19—C28	−178.90 (19)
O1—C1—C5—C6	23.9 (3)	C18—C19—C20—O6	−1.9 (2)
O1—C1—C5—C11	−152.4 (2)	C18—C19—C20—C30	171.9 (2)
C2—C1—C5—C6	−158.3 (2)	C18—C19—C28—O7	−31.7 (3)
C2—C1—C5—C11	25.5 (3)	C18—C19—C28—O8	145.7 (2)
C5—C1—C2—N1	1.9 (4)	C20—C19—C28—O7	148.8 (2)
C5—C1—C2—C3	−177.3 (2)	C20—C19—C28—O8	−33.8 (3)
N1—C2—C3—C4	−178.5 (2)	C28—C19—C20—O6	177.7 (2)
N1—C2—C3—C12	4.0 (3)	C28—C19—C20—C30	−8.5 (4)
C1—C2—C3—C4	0.8 (2)	O6—C20—C30—O9	160.9 (2)
C1—C2—C3—C12	−176.7 (2)	O6—C20—C30—O10	−18.3 (2)
C2—C3—C4—O1	−2.0 (2)	C19—C20—C30—O9	−12.5 (4)
C2—C3—C4—C14	170.1 (2)	C19—C20—C30—O10	168.2 (2)
C2—C3—C12—O2	−36.7 (3)	C17—C21—C22—C23	−177.5 (2)
C2—C3—C12—O3	140.7 (2)	C17—C21—C27—C26	177.2 (2)
C4—C3—C12—O2	146.3 (2)	C22—C21—C27—C26	−1.6 (3)
C4—C3—C12—O3	−36.3 (3)	C27—C21—C22—C23	1.3 (3)
C12—C3—C4—O1	175.43 (19)	C21—C22—C23—C24	0.7 (4)
C12—C3—C4—C14	−12.4 (4)	C22—C23—C24—C25	176.0 (2)
O1—C4—C14—O4	157.8 (2)	C22—C23—C24—C26	−2.4 (4)
O1—C4—C14—O5	−21.6 (2)	C23—C24—C26—C27	2.1 (4)
C3—C4—C14—O4	−13.9 (4)	C25—C24—C26—C27	−176.3 (2)
C3—C4—C14—O5	166.7 (2)	C24—C26—C27—C21	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···O7^i	0.86	2.38	3.089 (3)	140
N2—H201···O2^ii	0.86	2.64	3.253 (2)	129

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