Methyl 2-amino-4-(4-nitro­phenyl)-5-oxo-5,6-di­hydro-4H-pyrano[3,2-c]­quinoline-3-carboxyl­ate di­methyl­form­amide solvate

The title compound, C₂₀H₁₅N₃O₆·C₃H₇NO, was synthesized by the reaction of methyl cyano­acetate, 4-nitro­benz­aldehyde and 4-hydroxy­quinolin-2-one in EtOH catalysed by KF-alumina, followed by crystallization from dimethylformamide. X-ray analysis reveals that the pyran ring adopts a boat conform­ation.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.065
• wR factor = 0.209
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2

Alert level C
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        N4'
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for       C21'
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         N4
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT430_ALERT_2_C Short Inter D...A Contact  O6     ..  O6      ..       2.89 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

methyl 2-amino-4-(4-nitrophenyl)-5,6-dihydro-4H-pyrano [3,2-c] quinoline-5-one-3-carboxylate dimethylformamide solvate

Crystal data

C20H15N3O6·C3H7NO	Z = 2
Mr = 466.45	F(000) = 488
Triclinic, P1	Dx = 1.406 Mg m^−3
Hall symbol: -P 1	Melting point = 548–550 K
a = 8.312 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.696 (2) Å	Cell parameters from 33 reflections
c = 11.705 (1) Å	θ = 3.3–15.3°
α = 97.42 (1)°	µ = 0.11 mm^−1
β = 101.634 (9)°	T = 295 K
γ = 93.01 (1)°	Block, colorless
V = 1101.6 (3) Å^3	0.58 × 0.36 × 0.24 mm

Data collection

Siemens P4 diffractometer	Rint = 0.010
Radiation source: normal-focus sealed tube	θmax = 25.8°, θmin = 1.8°
Graphite monochromator	h = 0→10
ω scans	k = −14→14
4659 measured reflections	l = −14→14
4199 independent reflections	3 standard reflections every 97 reflections
2437 reflections with I > 2σ(I)	intensity decay: 4.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.209	w = 1/[σ^2(Fo^2) + (0.1169P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4199 reflections	Δρmax = 0.50 e Å^−3
341 parameters	Δρmin = −0.59 e Å^−3
8 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (5)

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)
O1	0.6462 (2)	0.21041 (17)	0.56822 (17)	0.0504 (6)
O2	0.1562 (2)	0.03109 (18)	0.63596 (17)	0.0533 (6)
O3	0.6733 (3)	0.10630 (18)	0.94637 (17)	0.0542 (6)
O4	0.9157 (2)	0.14923 (19)	0.8980 (2)	0.0608 (6)
O5	0.2561 (4)	0.6361 (3)	0.9357 (3)	0.1105 (11)*
O6	0.1711 (4)	0.5338 (3)	1.0541 (3)	0.0946 (9)*
N1	0.1719 (3)	0.0704 (2)	0.4533 (2)	0.0463 (6)
N2	0.8953 (3)	0.2166 (2)	0.6806 (3)	0.0618 (8)
H2A	0.9672	0.2102	0.7431	0.074*
H2B	0.9265	0.2385	0.6206	0.074*
N3	0.2314 (4)	0.5454 (3)	0.9712 (3)	0.0755 (9)
C1	0.4859 (3)	0.1628 (2)	0.5346 (2)	0.0409 (7)
C2	0.4151 (4)	0.1600 (2)	0.4116 (2)	0.0440 (7)
C3	0.4977 (4)	0.2017 (3)	0.3298 (3)	0.0596 (9)
H3	0.6080	0.2293	0.3530	0.071*
C4	0.4152 (5)	0.2014 (3)	0.2155 (3)	0.0696 (10)
H4	0.4689	0.2301	0.1614	0.083*
C5	0.2495 (5)	0.1578 (3)	0.1807 (3)	0.0696 (10)
H5	0.1935	0.1591	0.1037	0.084*
C6	0.1691 (4)	0.1134 (3)	0.2580 (3)	0.0582 (9)
H6	0.0603	0.0826	0.2331	0.070*
C7	0.2513 (4)	0.1144 (2)	0.3746 (2)	0.0455 (7)
C8	0.2370 (3)	0.0729 (2)	0.5710 (2)	0.0408 (7)
C9	0.4033 (3)	0.1267 (2)	0.6126 (2)	0.0377 (6)
C10	0.4773 (3)	0.1448 (2)	0.7426 (2)	0.0385 (6)
H10	0.4454	0.0765	0.7760	0.046*
C11	0.6633 (3)	0.1577 (2)	0.7612 (2)	0.0414 (7)
C12	0.7367 (3)	0.1930 (2)	0.6770 (3)	0.0451 (7)
C13	0.4097 (3)	0.2501 (2)	0.8020 (2)	0.0367 (6)
C14	0.4602 (4)	0.3610 (2)	0.7861 (3)	0.0536 (8)
H14	0.5361	0.3702	0.7388	0.064*
C15	0.4011 (4)	0.4573 (3)	0.8384 (3)	0.0600 (9)
H15	0.4348	0.5309	0.8256	0.072*
C16	0.2915 (4)	0.4430 (3)	0.9096 (3)	0.0502 (8)
C17	0.2369 (4)	0.3354 (3)	0.9271 (3)	0.0564 (8)
H17	0.1619	0.3270	0.9751	0.068*
C18	0.2952 (4)	0.2398 (3)	0.8720 (3)	0.0507 (8)
H18	0.2568	0.1665	0.8821	0.061*
C19	0.7649 (4)	0.1390 (2)	0.8718 (3)	0.0462 (7)
C20	0.7638 (5)	0.0869 (3)	1.0602 (3)	0.0696 (10)
H20A	0.8269	0.1570	1.0999	0.083*
H20B	0.8366	0.0271	1.0500	0.083*
H20C	0.6879	0.0637	1.1065	0.083*
O7	−0.042 (9)	0.304 (15)	0.471 (6)	0.161 (5)	0.497 (8)
N4	0.1363 (15)	0.4140 (15)	0.4024 (9)	0.079 (9)	0.497 (8)
C21	0.0896 (15)	0.3570 (8)	0.4803 (11)	0.117 (5)	0.497 (8)
H21	0.1660	0.3570	0.5503	0.140*	0.497 (8)
C22	0.036 (2)	0.4194 (15)	0.2910 (10)	0.164 (5)	0.497 (8)
H22A	0.0741	0.3705	0.2315	0.197*	0.497 (8)
H22B	0.0400	0.4977	0.2745	0.197*	0.497 (8)
H22C	−0.0761	0.3939	0.2911	0.197*	0.497 (8)
C23	0.2917 (14)	0.4775 (11)	0.4329 (19)	0.151 (7)	0.497 (8)
H23A	0.2785	0.5565	0.4612	0.181*	0.497 (8)
H23B	0.3400	0.4745	0.3648	0.181*	0.497 (8)
H23C	0.3623	0.4446	0.4935	0.181*	0.497 (8)
O7'	−0.028 (9)	0.303 (14)	0.472 (6)	0.161 (5)	0.503 (8)
N4'	0.1264 (15)	0.4172 (15)	0.3969 (10)	0.090 (9)	0.503 (8)
C21'	−0.0029 (12)	0.3463 (7)	0.3889 (11)	0.084 (3)	0.503 (8)
H21'	−0.0775	0.3287	0.3171	0.101*	0.503 (8)
C22'	0.234 (2)	0.4330 (15)	0.5084 (11)	0.164 (5)	0.503 (8)
H22D	0.2731	0.5132	0.5302	0.197*	0.503 (8)
H22E	0.3267	0.3875	0.5050	0.197*	0.503 (8)
H22F	0.1773	0.4090	0.5659	0.197*	0.503 (8)
C23'	0.169 (2)	0.4589 (12)	0.2983 (14)	0.135 (6)	0.503 (8)
H23D	0.2740	0.4333	0.2886	0.162*	0.503 (8)
H23E	0.1756	0.5419	0.3102	0.162*	0.503 (8)
H23F	0.0868	0.4299	0.2290	0.162*	0.503 (8)
H1N	0.079 (5)	0.039 (3)	0.428 (3)	0.070 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0398 (11)	0.0559 (12)	0.0535 (12)	−0.0069 (9)	0.0051 (9)	0.0120 (10)
O2	0.0388 (11)	0.0671 (14)	0.0478 (12)	−0.0150 (10)	0.0020 (10)	0.0039 (10)
O3	0.0517 (12)	0.0574 (13)	0.0488 (12)	0.0013 (10)	−0.0030 (10)	0.0134 (10)
O4	0.0382 (12)	0.0617 (14)	0.0738 (15)	0.0004 (10)	−0.0092 (10)	0.0113 (11)
N1	0.0380 (14)	0.0475 (14)	0.0457 (14)	−0.0080 (11)	−0.0024 (12)	0.0008 (11)
N2	0.0368 (14)	0.0767 (19)	0.0713 (18)	−0.0053 (13)	0.0085 (13)	0.0169 (15)
N3	0.086 (2)	0.0611 (19)	0.070 (2)	−0.0087 (16)	0.0019 (17)	0.0043 (15)
C1	0.0378 (15)	0.0336 (14)	0.0480 (16)	−0.0007 (11)	0.0048 (13)	0.0017 (12)
C2	0.0511 (17)	0.0369 (15)	0.0414 (16)	0.0023 (13)	0.0067 (13)	0.0014 (12)
C3	0.068 (2)	0.057 (2)	0.0528 (19)	−0.0044 (16)	0.0138 (17)	0.0065 (15)
C4	0.096 (3)	0.065 (2)	0.049 (2)	0.001 (2)	0.018 (2)	0.0093 (16)
C5	0.095 (3)	0.065 (2)	0.0420 (18)	0.004 (2)	−0.0008 (19)	0.0046 (16)
C6	0.068 (2)	0.0517 (18)	0.0453 (18)	0.0028 (16)	−0.0064 (16)	−0.0006 (14)
C7	0.0537 (17)	0.0359 (15)	0.0415 (16)	0.0037 (13)	0.0025 (14)	−0.0027 (12)
C8	0.0352 (14)	0.0387 (15)	0.0425 (16)	−0.0014 (12)	−0.0007 (12)	−0.0008 (12)
C9	0.0346 (14)	0.0339 (14)	0.0413 (15)	0.0002 (11)	0.0031 (12)	0.0022 (11)
C10	0.0345 (14)	0.0351 (14)	0.0429 (15)	−0.0036 (11)	0.0011 (12)	0.0078 (11)
C11	0.0351 (14)	0.0348 (14)	0.0508 (16)	−0.0011 (11)	0.0017 (13)	0.0066 (12)
C12	0.0356 (15)	0.0403 (15)	0.0547 (18)	0.0000 (12)	0.0021 (13)	0.0029 (13)
C13	0.0334 (13)	0.0357 (14)	0.0346 (14)	−0.0045 (11)	−0.0057 (11)	0.0043 (11)
C14	0.063 (2)	0.0432 (17)	0.0567 (18)	−0.0039 (15)	0.0199 (16)	0.0069 (14)
C15	0.075 (2)	0.0370 (16)	0.065 (2)	−0.0011 (15)	0.0106 (18)	0.0069 (15)
C16	0.0456 (17)	0.0440 (17)	0.0524 (17)	0.0047 (13)	−0.0008 (14)	−0.0079 (13)
C17	0.0534 (18)	0.058 (2)	0.0568 (19)	−0.0010 (15)	0.0155 (15)	0.0002 (15)
C18	0.0503 (17)	0.0434 (17)	0.0582 (19)	−0.0055 (13)	0.0152 (15)	0.0050 (14)
C19	0.0421 (17)	0.0321 (14)	0.0581 (18)	0.0021 (12)	−0.0024 (14)	0.0034 (13)
C20	0.081 (2)	0.064 (2)	0.055 (2)	0.0078 (19)	−0.0134 (18)	0.0180 (17)
O7	0.201 (10)	0.118 (4)	0.217 (5)	0.029 (11)	0.141 (6)	0.059 (4)
N4	0.114 (17)	0.071 (12)	0.081 (10)	0.029 (10)	0.061 (10)	0.047 (8)
C21	0.062 (6)	0.064 (6)	0.212 (16)	−0.003 (5)	0.027 (9)	−0.027 (8)
C22	0.191 (13)	0.168 (11)	0.113 (8)	0.099 (10)	−0.015 (8)	−0.016 (7)
C23	0.119 (11)	0.089 (8)	0.25 (2)	−0.014 (8)	0.066 (14)	0.023 (11)
O7'	0.201 (10)	0.118 (4)	0.217 (5)	0.029 (11)	0.141 (6)	0.059 (4)
N4'	0.067 (10)	0.057 (11)	0.137 (17)	−0.014 (8)	0.016 (9)	−0.001 (9)
C21'	0.086 (7)	0.084 (6)	0.096 (7)	0.004 (5)	0.047 (6)	0.023 (5)
C22'	0.191 (13)	0.168 (11)	0.113 (8)	0.099 (10)	−0.015 (8)	−0.016 (7)
C23'	0.138 (12)	0.106 (9)	0.210 (16)	0.048 (9)	0.100 (13)	0.097 (11)

Geometric parameters (Å, º)

O1—C1	1.376 (3)	C13—C14	1.389 (4)
O1—C12	1.388 (3)	C14—C15	1.373 (4)
O2—C8	1.239 (3)	C14—H14	0.93
O3—C19	1.346 (4)	C15—C16	1.371 (4)
O3—C20	1.444 (3)	C15—H15	0.93
O4—C19	1.224 (3)	C16—C17	1.370 (4)
O5—N3	1.211 (4)	C17—C18	1.377 (4)
O6—N3	1.198 (4)	C17—H17	0.93
N1—C8	1.371 (3)	C18—H18	0.93
N1—C7	1.371 (4)	C20—H20A	0.96
N1—H1N	0.82 (4)	C20—H20B	0.96
N2—C12	1.324 (4)	C20—H20C	0.96
N2—H2A	0.86	O7—C21	1.210 (3)
N2—H2B	0.86	N4—C21	1.303 (3)
N3—C16	1.479 (4)	N4—C23	1.411 (3)
C1—C9	1.343 (4)	N4—C22	1.412 (3)
C1—C2	1.437 (4)	C21—H21	0.93
C2—C7	1.397 (4)	C22—H22A	0.96
C2—C3	1.405 (4)	C22—H22B	0.96
C3—C4	1.375 (4)	C22—H22C	0.96
C3—H3	0.93	C23—H23A	0.96
C4—C5	1.403 (5)	C23—H23B	0.96
C4—H4	0.93	C23—H23C	0.96
C5—C6	1.365 (5)	O7'—C21'	1.210 (3)
C5—H5	0.93	N4'—C21'	1.303 (3)
C6—C7	1.396 (4)	N4'—C23'	1.410 (3)
C6—H6	0.93	N4'—C22'	1.412 (3)
C8—C9	1.451 (4)	C21'—H21'	0.93
C9—C10	1.504 (4)	C22'—H22D	0.96
C10—C11	1.514 (4)	C22'—H22E	0.96
C10—C13	1.525 (4)	C22'—H22F	0.96
C10—H10	0.98	C23'—H23D	0.96
C11—C12	1.355 (4)	C23'—H23E	0.96
C11—C19	1.445 (4)	C23'—H23F	0.96
C13—C18	1.385 (4)
C1—O1—C12	118.1 (2)	C18—C13—C10	122.1 (2)
C19—O3—C20	115.8 (2)	C14—C13—C10	120.6 (3)
C8—N1—C7	125.2 (3)	C15—C14—C13	121.8 (3)
C8—N1—H1N	117 (2)	C15—C14—H14	119.1
C7—N1—H1N	118 (2)	C13—C14—H14	119.1
C12—N2—H2A	120.0	C16—C15—C14	118.7 (3)
C12—N2—H2B	120.0	C16—C15—H15	120.6
H2A—N2—H2B	120.0	C14—C15—H15	120.6
O6—N3—O5	125.5 (4)	C17—C16—C15	121.6 (3)
O6—N3—C16	118.6 (3)	C17—C16—N3	118.5 (3)
O5—N3—C16	115.8 (3)	C15—C16—N3	119.9 (3)
C9—C1—O1	121.9 (2)	C16—C17—C18	118.7 (3)
C9—C1—C2	123.9 (3)	C16—C17—H17	120.6
O1—C1—C2	114.2 (2)	C18—C17—H17	120.6
C7—C2—C3	119.5 (3)	C17—C18—C13	121.8 (3)
C7—C2—C1	115.9 (3)	C17—C18—H18	119.1
C3—C2—C1	124.6 (3)	C13—C18—H18	119.1
C4—C3—C2	119.9 (3)	O4—C19—O3	122.0 (3)
C4—C3—H3	120.0	O4—C19—C11	126.4 (3)
C2—C3—H3	120.0	O3—C19—C11	111.6 (2)
C3—C4—C5	119.7 (3)	O3—C20—H20A	109.5
C3—C4—H4	120.2	O3—C20—H20B	109.5
C5—C4—H4	120.2	H20A—C20—H20B	109.5
C6—C5—C4	121.1 (3)	O3—C20—H20C	109.5
C6—C5—H5	119.4	H20A—C20—H20C	109.5
C4—C5—H5	119.4	H20B—C20—H20C	109.5
C5—C6—C7	119.6 (3)	C21—N4—C23	118.5 (11)
C5—C6—H6	120.2	C21—N4—C22	123.0 (13)
C7—C6—H6	120.2	C23—N4—C22	118.5 (13)
N1—C7—C6	120.2 (3)	O7—C21—N4	127.1 (16)
N1—C7—C2	119.7 (3)	O7—C21—H21	116.5
C6—C7—C2	120.1 (3)	N4—C21—H21	116.5
O2—C8—N1	120.9 (2)	C21'—N4'—C23'	122.8 (10)
O2—C8—C9	123.2 (2)	C21'—N4'—C22'	114.0 (13)
N1—C8—C9	115.9 (3)	C23'—N4'—C22'	122.3 (13)
C1—C9—C8	119.2 (2)	O7'—C21'—N4'	122 (2)
C1—C9—C10	121.5 (2)	O7'—C21'—H21'	119.2
C8—C9—C10	119.3 (2)	N4'—C21'—H21'	119.2
C9—C10—C11	109.4 (2)	N4'—C22'—H22D	109.5
C9—C10—C13	109.5 (2)	N4'—C22'—H22E	109.5
C11—C10—C13	112.0 (2)	H22D—C22'—H22E	109.5
C9—C10—H10	108.6	N4'—C22'—H22F	109.5
C11—C10—H10	108.6	H22D—C22'—H22F	109.5
C13—C10—H10	108.6	H22E—C22'—H22F	109.5
C12—C11—C19	119.0 (3)	N4'—C23'—H23D	109.5
C12—C11—C10	120.5 (2)	N4'—C23'—H23E	109.5
C19—C11—C10	120.4 (3)	H23D—C23'—H23E	109.5
N2—C12—C11	129.0 (3)	N4'—C23'—H23F	109.5
N2—C12—O1	109.2 (3)	H23D—C23'—H23F	109.5
C11—C12—O1	121.8 (2)	H23E—C23'—H23F	109.5
C18—C13—C14	117.4 (3)
C12—O1—C1—C9	17.1 (4)	C13—C10—C11—C19	78.4 (3)
C12—O1—C1—C2	−165.4 (2)	C19—C11—C12—N2	−1.6 (5)
C9—C1—C2—C7	−1.3 (4)	C10—C11—C12—N2	174.9 (3)
O1—C1—C2—C7	−178.8 (2)	C19—C11—C12—O1	178.8 (2)
C9—C1—C2—C3	177.3 (3)	C10—C11—C12—O1	−4.7 (4)
O1—C1—C2—C3	−0.2 (4)	C1—O1—C12—N2	163.3 (2)
C7—C2—C3—C4	2.6 (4)	C1—O1—C12—C11	−17.0 (4)
C1—C2—C3—C4	−176.0 (3)	C9—C10—C13—C18	106.5 (3)
C2—C3—C4—C5	−1.0 (5)	C11—C10—C13—C18	−132.0 (3)
C3—C4—C5—C6	−1.2 (5)	C9—C10—C13—C14	−72.6 (3)
C4—C5—C6—C7	1.9 (5)	C11—C10—C13—C14	48.9 (3)
C8—N1—C7—C6	−176.1 (3)	C18—C13—C14—C15	0.7 (4)
C8—N1—C7—C2	4.0 (4)	C10—C13—C14—C15	179.9 (3)
C5—C6—C7—N1	179.8 (3)	C13—C14—C15—C16	1.2 (5)
C5—C6—C7—C2	−0.3 (5)	C14—C15—C16—C17	−1.8 (5)
C3—C2—C7—N1	178.0 (3)	C14—C15—C16—N3	177.3 (3)
C1—C2—C7—N1	−3.3 (4)	O6—N3—C16—C17	17.8 (5)
C3—C2—C7—C6	−1.9 (4)	O5—N3—C16—C17	−165.9 (3)
C1—C2—C7—C6	176.8 (3)	O6—N3—C16—C15	−161.3 (3)
C7—N1—C8—O2	179.9 (3)	O5—N3—C16—C15	15.0 (5)
C7—N1—C8—C9	0.0 (4)	C15—C16—C17—C18	0.5 (5)
O1—C1—C9—C8	−177.5 (2)	N3—C16—C17—C18	−178.6 (3)
C2—C1—C9—C8	5.2 (4)	C16—C17—C18—C13	1.4 (5)
O1—C1—C9—C10	4.7 (4)	C14—C13—C18—C17	−2.0 (4)
C2—C1—C9—C10	−172.6 (2)	C10—C13—C18—C17	178.9 (3)
O2—C8—C9—C1	175.6 (3)	C20—O3—C19—O4	1.5 (4)
N1—C8—C9—C1	−4.5 (4)	C20—O3—C19—C11	−179.2 (2)
O2—C8—C9—C10	−6.6 (4)	C12—C11—C19—O4	−1.8 (4)
N1—C8—C9—C10	173.4 (2)	C10—C11—C19—O4	−178.3 (3)
C1—C9—C10—C11	−23.7 (3)	C12—C11—C19—O3	178.9 (2)
C8—C9—C10—C11	158.5 (2)	C10—C11—C19—O3	2.3 (3)
C1—C9—C10—C13	99.4 (3)	C23—N4—C21—O7	175 (12)
C8—C9—C10—C13	−78.4 (3)	C22—N4—C21—O7	−2 (12)
C9—C10—C11—C12	23.5 (3)	C23'—N4'—C21'—O7'	173 (11)
C13—C10—C11—C12	−98.1 (3)	C22'—N4'—C21'—O7'	3 (11)
C9—C10—C11—C19	−160.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.82 (4)	2.03 (4)	2.851 (3)	177 (3)
N2—H2A···O4	0.86	2.14	2.735 (4)	126
N2—H2B···O7^ii	0.86	2.05	2.901 (19)	169
N2—H2B···O7′^ii	0.86	2.07	2.92 (2)	172

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