Methyl 2-amino-4-(3-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 2-cyano-3-(3-nitro­phenyl)­acryl­ate and 4-hydroxy­quinolin-2-one in ethanol, catalysed by KF-alumina. 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) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N3
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        N4'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H7 N O

   0 ALERT level A = In general: serious problem
   0 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
   1 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-(3-nitrophenyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline- 3-carboxylate dimethylformamide solvate

Crystal data

C20H15N3O6·C3H7NO	Z = 2
Mr = 466.45	F(000) = 488
Triclinic, P1	Dx = 1.382 Mg m^−3
Hall symbol: -P 1	Melting point = 541–542 K
a = 8.216 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.695 (2) Å	Cell parameters from 33 reflections
c = 12.204 (2) Å	θ = 2.8–14.8°
α = 77.44 (1)°	µ = 0.10 mm^−1
β = 89.00 (1)°	T = 295 K
γ = 78.40 (1)°	Block, colorless
V = 1120.8 (3) Å^3	0.56 × 0.34 × 0.18 mm

Data collection

Siemens P4 diffractometer	Rint = 0.010
Radiation source: normal-focus sealed tube	θmax = 25.8°, θmin = 1.7°
Graphite monochromator	h = 0→9
ω scans	k = −13→13
4712 measured reflections	l = −14→14
4242 independent reflections	3 standard reflections every 97 reflections
2583 reflections with I > 2σ(I)	intensity decay: 3.2%

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0606P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
4242 reflections	Δρmax = 0.24 e Å^−3
361 parameters	Δρmin = −0.16 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: 0.016 (2)

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	0.36752 (15)	0.58282 (11)	0.78986 (11)	0.0492 (4)
O2	0.84405 (15)	0.64142 (11)	0.96745 (12)	0.0521 (4)
O3	0.6812 (3)	0.9026 (2)	0.36326 (15)	0.1081 (7)
O4	0.5495 (3)	0.7678 (2)	0.43762 (15)	0.1185 (8)
O5	0.33116 (17)	0.95581 (12)	0.88630 (11)	0.0531 (4)
O6	0.09121 (17)	0.91405 (13)	0.83719 (13)	0.0668 (4)
N1	0.83069 (18)	0.45841 (13)	0.93814 (12)	0.0426 (4)
H1	0.9257	0.4297	0.9721	0.051*
N2	0.1172 (2)	0.6990 (2)	0.77310 (18)	0.0647 (6)
N3	0.6269 (3)	0.8436 (2)	0.44442 (16)	0.0725 (6)
C1	0.5242 (2)	0.54577 (16)	0.83970 (14)	0.0393 (4)
C2	0.5955 (2)	0.42157 (16)	0.84772 (14)	0.0405 (4)
C3	0.5194 (3)	0.34083 (18)	0.80744 (17)	0.0529 (5)
H3	0.4121	0.3657	0.7766	0.063*
C4	0.6027 (3)	0.22579 (19)	0.81353 (18)	0.0602 (6)
H4	0.5522	0.1729	0.7861	0.072*
C5	0.7627 (3)	0.18751 (18)	0.86062 (17)	0.0575 (6)
H5	0.8187	0.1094	0.8636	0.069*
C6	0.8384 (3)	0.26355 (16)	0.90256 (16)	0.0490 (5)
H6	0.9446	0.2369	0.9351	0.059*
C7	0.7554 (2)	0.38131 (15)	0.89631 (14)	0.0398 (4)
C8	0.7661 (2)	0.57668 (16)	0.92980 (14)	0.0395 (4)
C9	0.6040 (2)	0.62190 (15)	0.87456 (14)	0.0362 (4)
C10	0.5317 (2)	0.75358 (15)	0.85392 (14)	0.0386 (4)
H10	0.5546	0.7826	0.9204	0.046*
C11	0.3450 (2)	0.77419 (17)	0.83628 (15)	0.0425 (5)
C12	0.2752 (2)	0.69144 (18)	0.80190 (15)	0.0456 (5)
C13	0.6123 (2)	0.82126 (15)	0.75298 (15)	0.0374 (4)
C14	0.7132 (2)	0.89947 (17)	0.76360 (17)	0.0506 (5)
H14	0.7350	0.9109	0.8345	0.061*
C15	0.7827 (3)	0.9612 (2)	0.6712 (2)	0.0642 (6)
H15	0.8496	1.0140	0.6806	0.077*
C16	0.7535 (3)	0.94508 (19)	0.56550 (19)	0.0602 (6)
H16	0.7987	0.9868	0.5026	0.072*
C17	0.6556 (2)	0.86538 (18)	0.55596 (16)	0.0494 (5)
C18	0.5845 (2)	0.80423 (16)	0.64651 (15)	0.0440 (5)
H18	0.5178	0.7515	0.6366	0.053*
C19	0.2419 (2)	0.88482 (18)	0.85158 (16)	0.0485 (5)
C20	0.2391 (3)	1.06824 (19)	0.90588 (19)	0.0705 (7)
H20A	0.1851	1.1158	0.8371	0.085*
H20B	0.3139	1.1103	0.9323	0.085*
H20C	0.1570	1.0533	0.9612	0.085*
H2A	0.093 (3)	0.638 (2)	0.7570 (18)	0.059 (7)*
H2B	0.053 (3)	0.760 (2)	0.7833 (19)	0.068 (8)*
N4	−0.1277 (11)	0.4049 (7)	0.5935 (10)	0.071 (4)	0.649 (8)
O7	−0.0227 (13)	0.5242 (9)	0.6879 (14)	0.130 (3)	0.649 (8)
C21	−0.0219 (10)	0.4323 (7)	0.6571 (5)	0.097 (3)	0.649 (8)
H21	0.0692	0.3712	0.6829	0.116*	0.649 (8)
C23	−0.2744 (10)	0.4887 (6)	0.5504 (9)	0.130 (3)	0.649 (8)
H23A	−0.3693	0.4623	0.5864	0.155*	0.649 (8)
H23B	−0.2843	0.4952	0.4710	0.155*	0.649 (8)
H23C	−0.2688	0.5653	0.5648	0.155*	0.649 (8)
C22	−0.1044 (12)	0.2899 (6)	0.5682 (6)	0.113 (2)	0.649 (8)
H22A	−0.0076	0.2392	0.6083	0.136*	0.649 (8)
H22B	−0.0899	0.2969	0.4890	0.136*	0.649 (8)
H22C	−0.2001	0.2557	0.5903	0.136*	0.649 (8)
N4'	−0.119 (2)	0.4123 (14)	0.599 (2)	0.077 (8)	0.351 (8)
O7'	0.030 (2)	0.496 (2)	0.688 (3)	0.132 (6)	0.351 (8)
C21'	−0.1063 (14)	0.5139 (14)	0.6439 (10)	0.091 (5)	0.351 (8)
H21'	−0.1887	0.5823	0.6393	0.109*	0.351 (8)
C22'	−0.0026 (19)	0.3111 (12)	0.6035 (12)	0.117 (5)	0.351 (8)
H22D	−0.0483	0.2428	0.6377	0.140*	0.351 (8)
H22E	0.0924	0.3133	0.6470	0.140*	0.351 (8)
H22F	0.0303	0.3054	0.5287	0.140*	0.351 (8)
C23'	−0.266 (2)	0.4268 (14)	0.5355 (18)	0.130 (3)	0.351 (8)
H23D	−0.2387	0.4101	0.4631	0.155*	0.351 (8)
H23E	−0.3274	0.5076	0.5264	0.155*	0.351 (8)
H23F	−0.3332	0.3727	0.5736	0.155*	0.351 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (7)	0.0533 (8)	0.0567 (8)	−0.0022 (6)	−0.0105 (6)	−0.0160 (7)
O2	0.0435 (8)	0.0441 (8)	0.0678 (9)	−0.0018 (6)	−0.0179 (7)	−0.0154 (7)
O3	0.1391 (18)	0.1279 (17)	0.0484 (11)	−0.0250 (14)	0.0201 (11)	−0.0035 (11)
O4	0.198 (2)	0.1255 (18)	0.0527 (11)	−0.0708 (18)	−0.0087 (13)	−0.0275 (11)
O5	0.0522 (8)	0.0463 (8)	0.0571 (9)	0.0031 (7)	0.0042 (7)	−0.0158 (7)
O6	0.0411 (8)	0.0720 (10)	0.0787 (11)	0.0120 (7)	−0.0030 (7)	−0.0194 (8)
N1	0.0377 (8)	0.0382 (9)	0.0475 (9)	0.0011 (7)	−0.0119 (7)	−0.0070 (7)
N2	0.0374 (11)	0.0676 (15)	0.0901 (16)	−0.0011 (11)	−0.0076 (10)	−0.0276 (12)
N3	0.0922 (16)	0.0758 (15)	0.0435 (12)	−0.0077 (12)	0.0011 (11)	−0.0091 (11)
C1	0.0343 (10)	0.0463 (11)	0.0337 (10)	−0.0022 (8)	−0.0025 (8)	−0.0060 (8)
C2	0.0437 (11)	0.0425 (11)	0.0346 (10)	−0.0087 (9)	0.0003 (8)	−0.0071 (8)
C3	0.0566 (13)	0.0515 (13)	0.0523 (12)	−0.0123 (10)	−0.0071 (10)	−0.0132 (10)
C4	0.0795 (16)	0.0485 (13)	0.0585 (14)	−0.0196 (12)	−0.0056 (12)	−0.0174 (10)
C5	0.0777 (16)	0.0381 (11)	0.0543 (13)	−0.0051 (11)	−0.0029 (12)	−0.0109 (10)
C6	0.0537 (12)	0.0400 (11)	0.0484 (12)	0.0001 (9)	−0.0041 (9)	−0.0074 (9)
C7	0.0445 (11)	0.0389 (11)	0.0346 (10)	−0.0062 (9)	0.0010 (8)	−0.0069 (8)
C8	0.0377 (10)	0.0402 (11)	0.0374 (10)	−0.0026 (9)	−0.0034 (8)	−0.0060 (8)
C9	0.0337 (9)	0.0391 (10)	0.0333 (9)	−0.0025 (8)	0.0000 (7)	−0.0070 (8)
C10	0.0377 (10)	0.0399 (10)	0.0360 (10)	0.0014 (8)	−0.0044 (8)	−0.0114 (8)
C11	0.0353 (10)	0.0493 (11)	0.0388 (10)	0.0007 (9)	−0.0006 (8)	−0.0090 (9)
C12	0.0329 (10)	0.0551 (13)	0.0428 (11)	0.0029 (9)	−0.0019 (8)	−0.0086 (9)
C13	0.0321 (9)	0.0337 (10)	0.0423 (10)	0.0035 (8)	−0.0046 (8)	−0.0089 (8)
C14	0.0545 (12)	0.0476 (12)	0.0516 (12)	−0.0112 (10)	−0.0070 (10)	−0.0134 (10)
C15	0.0638 (14)	0.0576 (14)	0.0722 (16)	−0.0258 (12)	−0.0036 (12)	−0.0038 (12)
C16	0.0576 (14)	0.0567 (14)	0.0577 (14)	−0.0093 (11)	0.0066 (11)	0.0033 (11)
C17	0.0540 (12)	0.0501 (12)	0.0381 (11)	0.0010 (10)	−0.0018 (9)	−0.0070 (9)
C18	0.0468 (11)	0.0416 (11)	0.0422 (11)	−0.0061 (9)	−0.0033 (9)	−0.0089 (9)
C19	0.0404 (11)	0.0552 (13)	0.0423 (11)	0.0051 (10)	0.0017 (9)	−0.0083 (9)
C20	0.0808 (17)	0.0554 (14)	0.0635 (15)	0.0163 (12)	0.0129 (12)	−0.0163 (11)
N4	0.073 (7)	0.074 (7)	0.061 (5)	−0.018 (5)	0.003 (4)	−0.003 (4)
O7	0.169 (7)	0.165 (7)	0.111 (6)	−0.119 (5)	0.044 (7)	−0.069 (6)
C21	0.115 (5)	0.132 (7)	0.071 (4)	−0.083 (6)	0.030 (3)	−0.028 (4)
C23	0.105 (3)	0.128 (8)	0.118 (5)	0.017 (5)	0.025 (3)	0.015 (6)
C22	0.141 (7)	0.100 (5)	0.108 (5)	−0.043 (4)	0.034 (5)	−0.028 (3)
N4'	0.074 (13)	0.094 (15)	0.088 (12)	−0.050 (11)	0.029 (9)	−0.046 (9)
O7'	0.131 (10)	0.165 (11)	0.114 (10)	−0.054 (9)	0.033 (9)	−0.043 (8)
C21'	0.096 (9)	0.065 (7)	0.095 (9)	−0.001 (6)	0.040 (7)	0.000 (6)
C22'	0.113 (10)	0.088 (8)	0.129 (11)	0.011 (8)	0.030 (8)	−0.011 (7)
C23'	0.105 (3)	0.128 (8)	0.118 (5)	0.017 (5)	0.025 (3)	0.015 (6)

Geometric parameters (Å, º)

O1—C12	1.379 (2)	C13—C18	1.386 (2)
O1—C1	1.379 (2)	C14—C15	1.381 (3)
O2—C8	1.245 (2)	C14—H14	0.9300
O3—N3	1.212 (2)	C15—C16	1.376 (3)
O4—N3	1.207 (3)	C15—H15	0.9300
O5—C19	1.347 (2)	C16—C17	1.372 (3)
O5—C20	1.445 (2)	C16—H16	0.9300
O6—C19	1.221 (2)	C17—C18	1.370 (3)
N1—C8	1.360 (2)	C18—H18	0.9300
N1—C7	1.375 (2)	C20—H20A	0.9600
N1—H1	0.8600	C20—H20B	0.9600
N2—C12	1.331 (3)	C20—H20C	0.9600
N2—H2A	0.84 (2)	N4—C21	1.305 (3)
N2—H2B	0.83 (2)	N4—C23	1.419 (3)
N3—C17	1.470 (3)	N4—C22	1.420 (3)
C1—C9	1.347 (2)	O7—C21	1.213 (3)
C1—C2	1.436 (2)	C21—H21	0.9300
C2—C7	1.399 (2)	C23—H23A	0.9600
C2—C3	1.405 (3)	C23—H23B	0.9600
C3—C4	1.368 (3)	C23—H23C	0.9600
C3—H3	0.9300	C22—H22A	0.9600
C4—C5	1.391 (3)	C22—H22B	0.9600
C4—H4	0.9300	C22—H22C	0.9600
C5—C6	1.368 (3)	N4'—C22'	1.356 (2)
C5—H5	0.9300	N4'—C23'	1.414 (3)
C6—C7	1.395 (2)	N4'—C21'	1.432 (16)
C6—H6	0.9300	O7'—C21'	1.211 (3)
C8—C9	1.450 (2)	C21'—H21'	0.9300
C9—C10	1.502 (2)	C22'—H22D	0.9600
C10—C11	1.515 (2)	C22'—H22E	0.9600
C10—C13	1.530 (2)	C22'—H22F	0.9600
C10—H10	0.9800	C23'—H23D	0.9600
C11—C12	1.360 (3)	C23'—H23E	0.9600
C11—C19	1.444 (3)	C23'—H23F	0.9600
C13—C14	1.379 (2)
C12—O1—C1	118.02 (14)	C14—C13—C10	122.33 (17)
C19—O5—C20	116.45 (16)	C18—C13—C10	119.62 (16)
C8—N1—C7	124.92 (15)	C13—C14—C15	121.47 (19)
C8—N1—H1	117.5	C13—C14—H14	119.3
C7—N1—H1	117.5	C15—C14—H14	119.3
C12—N2—H2A	116.5 (15)	C16—C15—C14	120.4 (2)
C12—N2—H2B	114.3 (16)	C16—C15—H15	119.8
H2A—N2—H2B	128 (2)	C14—C15—H15	119.8
O4—N3—O3	122.8 (2)	C17—C16—C15	117.8 (2)
O4—N3—C17	118.5 (2)	C17—C16—H16	121.1
O3—N3—C17	118.7 (2)	C15—C16—H16	121.1
C9—C1—O1	122.00 (16)	C18—C17—C16	122.63 (19)
C9—C1—C2	123.39 (16)	C18—C17—N3	118.49 (19)
O1—C1—C2	114.57 (16)	C16—C17—N3	118.9 (2)
C7—C2—C3	118.85 (18)	C17—C18—C13	119.69 (18)
C7—C2—C1	116.11 (16)	C17—C18—H18	120.2
C3—C2—C1	125.01 (18)	C13—C18—H18	120.2
C4—C3—C2	120.2 (2)	O6—C19—O5	121.77 (18)
C4—C3—H3	119.9	O6—C19—C11	126.2 (2)
C2—C3—H3	119.9	O5—C19—C11	112.05 (17)
C3—C4—C5	120.3 (2)	O5—C20—H20A	109.5
C3—C4—H4	119.8	O5—C20—H20B	109.5
C5—C4—H4	119.8	H20A—C20—H20B	109.5
C6—C5—C4	120.70 (19)	O5—C20—H20C	109.5
C6—C5—H5	119.7	H20A—C20—H20C	109.5
C4—C5—H5	119.7	H20B—C20—H20C	109.5
C5—C6—C7	119.64 (19)	C21—N4—C23	120.6 (7)
C5—C6—H6	120.2	C21—N4—C22	121.8 (6)
C7—C6—H6	120.2	C23—N4—C22	117.5 (6)
N1—C7—C6	120.03 (17)	O7—C21—N4	130.7 (10)
N1—C7—C2	119.68 (16)	O7—C21—H21	114.7
C6—C7—C2	120.29 (17)	N4—C21—H21	114.7
O2—C8—N1	121.08 (16)	C22'—N4'—C23'	117.6 (13)
O2—C8—C9	122.62 (16)	C22'—N4'—C21'	128.0 (15)
N1—C8—C9	116.30 (16)	C23'—N4'—C21'	114.1 (10)
C1—C9—C8	119.37 (16)	O7'—C21'—N4'	109 (2)
C1—C9—C10	121.52 (16)	O7'—C21'—H21'	125.7
C8—C9—C10	119.07 (15)	N4'—C21'—H21'	125.7
C9—C10—C11	109.42 (15)	N4'—C22'—H22D	109.5
C9—C10—C13	110.37 (14)	N4'—C22'—H22E	109.5
C11—C10—C13	111.32 (14)	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	119.98 (17)	N4'—C23'—H23D	109.5
C12—C11—C10	120.44 (16)	N4'—C23'—H23E	109.5
C19—C11—C10	119.52 (17)	H23D—C23'—H23E	109.5
N2—C12—C11	128.5 (2)	N4'—C23'—H23F	109.5
N2—C12—O1	109.35 (19)	H23D—C23'—H23F	109.5
C11—C12—O1	122.12 (16)	H23E—C23'—H23F	109.5
C14—C13—C18	118.05 (18)
C12—O1—C1—C9	−16.6 (2)	C13—C10—C11—C19	−78.0 (2)
C12—O1—C1—C2	165.28 (15)	C19—C11—C12—N2	3.7 (3)
C9—C1—C2—C7	1.0 (3)	C10—C11—C12—N2	−173.64 (19)
O1—C1—C2—C7	179.07 (15)	C19—C11—C12—O1	−177.70 (16)
C9—C1—C2—C3	−176.79 (18)	C10—C11—C12—O1	5.0 (3)
O1—C1—C2—C3	1.3 (3)	C1—O1—C12—N2	−165.06 (16)
C7—C2—C3—C4	−1.6 (3)	C1—O1—C12—C11	16.1 (3)
C1—C2—C3—C4	176.12 (18)	C9—C10—C13—C14	−112.71 (19)
C2—C3—C4—C5	0.7 (3)	C11—C10—C13—C14	125.59 (18)
C3—C4—C5—C6	0.7 (3)	C9—C10—C13—C18	67.2 (2)
C4—C5—C6—C7	−1.1 (3)	C11—C10—C13—C18	−54.5 (2)
C8—N1—C7—C6	175.38 (17)	C18—C13—C14—C15	1.2 (3)
C8—N1—C7—C2	−4.7 (3)	C10—C13—C14—C15	−178.94 (18)
C5—C6—C7—N1	−179.91 (17)	C13—C14—C15—C16	−0.5 (3)
C5—C6—C7—C2	0.2 (3)	C14—C15—C16—C17	−0.7 (3)
C3—C2—C7—N1	−178.77 (16)	C15—C16—C17—C18	1.3 (3)
C1—C2—C7—N1	3.3 (2)	C15—C16—C17—N3	−178.05 (19)
C3—C2—C7—C6	1.2 (3)	O4—N3—C17—C18	−4.1 (3)
C1—C2—C7—C6	−176.73 (16)	O3—N3—C17—C18	175.7 (2)
C7—N1—C8—O2	−178.16 (17)	O4—N3—C17—C16	175.3 (2)
C7—N1—C8—C9	1.5 (3)	O3—N3—C17—C16	−4.9 (3)
O1—C1—C9—C8	177.92 (15)	C16—C17—C18—C13	−0.7 (3)
C2—C1—C9—C8	−4.1 (3)	N3—C17—C18—C13	178.69 (17)
O1—C1—C9—C10	−4.3 (3)	C14—C13—C18—C17	−0.6 (3)
C2—C1—C9—C10	173.69 (15)	C10—C13—C18—C17	179.54 (16)
O2—C8—C9—C1	−177.48 (17)	C20—O5—C19—O6	0.1 (3)
N1—C8—C9—C1	2.9 (2)	C20—O5—C19—C11	−179.06 (15)
O2—C8—C9—C10	4.7 (3)	C12—C11—C19—O6	0.5 (3)
N1—C8—C9—C10	−174.97 (15)	C10—C11—C19—O6	177.89 (18)
C1—C9—C10—C11	22.7 (2)	C12—C11—C19—O5	179.68 (17)
C8—C9—C10—C11	−159.47 (15)	C10—C11—C19—O5	−2.9 (2)
C1—C9—C10—C13	−100.09 (19)	C23—N4—C21—O7	−2 (2)
C8—C9—C10—C13	77.70 (19)	C22—N4—C21—O7	−179.2 (13)
C9—C10—C11—C12	−22.9 (2)	C22'—N4'—C21'—O7'	0 (4)
C13—C10—C11—C12	99.4 (2)	C23'—N4'—C21'—O7'	−174 (3)
C9—C10—C11—C19	159.73 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	1.99	2.8460 (19)	173
N2—H2A···O7	0.84 (2)	2.10 (2)	2.914 (7)	163 (2)
N2—H2A···O7′	0.84 (2)	2.16 (3)	3.00 (2)	171 (2)
N2—H2B···O6	0.83 (2)	2.13 (2)	2.759 (3)	133 (2)

Symmetry code: (i) −x+2, −y+1, −z+2.