3-{2-[2-(3,5-Dinitro-2-oxidophenyl)ethyl]-3,3-dimethyl-3H-indol-1-ium-1-yl}propanoic acid bis­(di­methyl­form­amide) solvate

The crystal structure of the title compound, C₂₁H₁₉N₃O₇·2C₃H₇NO, has been prepared, for the first time in the dark, as the permanent merocyanine mode of the open form. It has a zwitterionic trans–transoid structure and is solvated with two N,N-di­methyl­form­amide (DMF) mol­ecules, forming O—H...O and C—H...O hydrogen bonds. The crystal structure is further stabilized by a variety of weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.153
• Data-to-parameter ratio = 13.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1'-(2-Carboxyethyl)-3',3'-dimethyl-6,8-dinitrospiro[2H-1-benzopyran- 2,2'(2H)-indole] bis(dimethylformamide) solvate

Crystal data

C21H19N3O7·2C3H7NO	Z = 2
Mr = 571.58	F(000) = 604
Triclinic, P1	Dx = 1.331 Mg m^−3
a = 10.633 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.078 (4) Å	Cell parameters from 636 reflections
c = 12.262 (4) Å	θ = 2.8–22.4°
α = 113.266 (6)°	µ = 0.10 mm^−1
β = 95.167 (6)°	T = 293 K
γ = 95.326 (6)°	Plate, red
V = 1426.6 (9) Å^3	0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4991 independent reflections
Radiation source: fine-focus sealed tube	2331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.958, Tmax = 1.000	k = −13→14
7300 measured reflections	l = −13→14

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)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0559P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4991 reflections	Δρmax = 0.17 e Å^−3
378 parameters	Δρmin = −0.18 e Å^−3
124 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: none

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	0.8221 (2)	0.5872 (3)	0.6455 (2)	0.0364 (7)
N2	0.4743 (3)	0.2938 (3)	1.0985 (3)	0.0555 (9)
N3	0.2492 (3)	0.2666 (3)	0.7288 (3)	0.0560 (9)
O1	0.7001 (2)	0.3953 (3)	1.0368 (2)	0.0637 (8)
O2	0.5468 (3)	0.3575 (3)	1.1892 (3)	0.0756 (9)
O3	0.3909 (4)	0.2175 (3)	1.0976 (3)	0.1048 (13)
O4	0.1564 (2)	0.2163 (3)	0.7517 (3)	0.0788 (10)
O5	0.2459 (2)	0.2866 (3)	0.6379 (3)	0.0789 (10)
O6	0.4908 (2)	0.6710 (3)	0.4957 (2)	0.0620 (8)
O7	0.5527 (3)	0.8665 (3)	0.6079 (3)	0.0814 (10)
H7A	0.4844	0.8778	0.5739	0.13 (2)*
C1	0.8204 (3)	0.5457 (3)	0.7304 (3)	0.0364 (9)
C2	0.9552 (3)	0.5625 (3)	0.7936 (3)	0.0389 (9)
C3	1.0315 (3)	0.6062 (3)	0.7172 (3)	0.0379 (9)
C4	1.1610 (3)	0.6293 (3)	0.7192 (3)	0.0472 (10)
H4	1.2180	0.6185	0.7751	0.057*
C5	1.2039 (3)	0.6687 (3)	0.6363 (3)	0.0512 (10)
H5	1.2912	0.6827	0.6352	0.061*
C6	1.1201 (3)	0.6881 (3)	0.5545 (3)	0.0512 (10)
H6	1.1522	0.7166	0.5009	0.061*
C7	0.9901 (3)	0.6659 (3)	0.5509 (3)	0.0472 (10)
H7	0.9330	0.6783	0.4962	0.057*
C8	0.9500 (3)	0.6242 (3)	0.6336 (3)	0.0366 (9)
C9	0.9685 (3)	0.6634 (4)	0.9207 (3)	0.0554 (11)
H9A	1.0559	0.6805	0.9570	0.083*
H9B	0.9158	0.6371	0.9679	0.083*
H9C	0.9422	0.7357	0.9165	0.083*
C10	0.9965 (3)	0.4460 (4)	0.7976 (3)	0.0540 (11)
H10A	0.9808	0.3820	0.7184	0.081*
H10B	0.9488	0.4226	0.8498	0.081*
H10C	1.0859	0.4602	0.8271	0.081*
C11	0.7060 (3)	0.4932 (3)	0.7532 (3)	0.0405 (9)
H11	0.6315	0.4842	0.7026	0.049*
C12	0.6968 (3)	0.4556 (3)	0.8419 (3)	0.0404 (9)
H12	0.7708	0.4695	0.8947	0.048*
C13	0.5844 (3)	0.3962 (3)	0.8641 (3)	0.0362 (9)
C14	0.5970 (3)	0.3717 (3)	0.9712 (3)	0.0414 (9)
C15	0.4797 (3)	0.3160 (3)	0.9912 (3)	0.0385 (9)
C16	0.3694 (3)	0.2810 (3)	0.9127 (3)	0.0431 (9)
H16	0.2975	0.2422	0.9276	0.052*
C17	0.3660 (3)	0.3040 (3)	0.8115 (3)	0.0410 (9)
C18	0.4711 (3)	0.3609 (3)	0.7871 (3)	0.0420 (9)
H18	0.4658	0.3758	0.7181	0.050*
C19	0.7122 (3)	0.6029 (3)	0.5736 (3)	0.0416 (9)
H19A	0.6378	0.5481	0.5701	0.050*
H19B	0.7303	0.5837	0.4925	0.050*
C20	0.6863 (3)	0.7329 (4)	0.6300 (3)	0.0477 (10)
H20A	0.6790	0.7546	0.7140	0.057*
H20B	0.7575	0.7864	0.6253	0.057*
C21	0.5665 (4)	0.7510 (4)	0.5692 (4)	0.0476 (10)
N4	0.2270 (4)	0.9048 (3)	0.3555 (3)	0.0706 (10)
O8	0.3476 (3)	0.9147 (3)	0.5204 (3)	0.0905 (11)
C22	0.3295 (5)	0.8881 (4)	0.4114 (5)	0.0765 (14)
H22	0.3927	0.8541	0.3663	0.092*
C23	0.1288 (4)	0.9612 (5)	0.4212 (5)	0.0954 (17)
H23A	0.0568	0.9008	0.4072	0.143*
H23B	0.1032	1.0220	0.3951	0.143*
H23C	0.1606	0.9987	0.5052	0.143*
C24	0.2151 (6)	0.8772 (5)	0.2293 (4)	0.121 (2)
H24A	0.2923	0.8508	0.1993	0.182*
H24B	0.2003	0.9488	0.2167	0.182*
H24C	0.1449	0.8138	0.1877	0.182*
N5	0.2212 (5)	−0.0388 (4)	0.8664 (4)	0.0890 (13)
O9	0.0087 (5)	−0.0516 (5)	0.8162 (5)	0.165 (2)
C25	0.1183 (8)	−0.0401 (6)	0.7972 (6)	0.116 (2)
H25A	0.1308	−0.0313	0.7267	0.139*
C26	0.2126 (6)	−0.0534 (5)	0.9757 (5)	0.132 (2)
H26A	0.2775	0.0031	1.0371	0.198*
H26B	0.2243	−0.1350	0.9638	0.198*
H26C	0.1301	−0.0381	0.9995	0.198*
C27	0.3447 (5)	−0.0362 (5)	0.8282 (5)	0.1145 (19)
H27A	0.3759	−0.1119	0.8150	0.172*
H27B	0.4025	0.0294	0.8890	0.172*
H27C	0.3383	−0.0244	0.7551	0.172*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0326 (16)	0.0457 (19)	0.0351 (17)	0.0009 (14)	0.0004 (13)	0.0226 (15)
N2	0.053 (2)	0.063 (3)	0.053 (2)	0.0008 (19)	0.0098 (19)	0.027 (2)
N3	0.041 (2)	0.066 (2)	0.069 (2)	−0.0021 (18)	−0.0018 (18)	0.040 (2)
O1	0.0425 (16)	0.106 (2)	0.0542 (17)	−0.0048 (16)	−0.0036 (14)	0.0500 (17)
O2	0.0542 (18)	0.125 (3)	0.0583 (19)	−0.0016 (19)	−0.0006 (16)	0.053 (2)
O3	0.142 (3)	0.103 (3)	0.062 (2)	−0.055 (2)	0.006 (2)	0.043 (2)
O4	0.0427 (17)	0.103 (3)	0.105 (2)	−0.0154 (17)	−0.0062 (16)	0.066 (2)
O5	0.0521 (18)	0.119 (3)	0.078 (2)	−0.0103 (17)	−0.0164 (16)	0.063 (2)
O6	0.0483 (17)	0.072 (2)	0.0618 (18)	0.0047 (16)	−0.0110 (14)	0.0276 (16)
O7	0.063 (2)	0.067 (2)	0.114 (3)	0.0167 (17)	−0.0133 (18)	0.040 (2)
C1	0.032 (2)	0.045 (2)	0.035 (2)	0.0027 (17)	0.0018 (16)	0.0204 (18)
C2	0.033 (2)	0.052 (2)	0.036 (2)	−0.0007 (18)	−0.0010 (16)	0.0241 (19)
C3	0.033 (2)	0.045 (2)	0.036 (2)	0.0008 (18)	0.0009 (17)	0.0178 (18)
C4	0.033 (2)	0.064 (3)	0.045 (2)	0.0006 (19)	−0.0024 (18)	0.026 (2)
C5	0.038 (2)	0.062 (3)	0.048 (2)	0.000 (2)	0.0087 (19)	0.018 (2)
C6	0.051 (3)	0.059 (3)	0.047 (2)	−0.004 (2)	0.012 (2)	0.026 (2)
C7	0.044 (2)	0.057 (3)	0.044 (2)	−0.001 (2)	−0.0007 (19)	0.027 (2)
C8	0.033 (2)	0.040 (2)	0.039 (2)	0.0018 (17)	0.0058 (17)	0.0194 (18)
C9	0.049 (2)	0.073 (3)	0.040 (2)	−0.006 (2)	−0.0004 (19)	0.023 (2)
C10	0.042 (2)	0.074 (3)	0.060 (3)	0.007 (2)	0.001 (2)	0.043 (2)
C11	0.030 (2)	0.052 (2)	0.042 (2)	0.0040 (18)	−0.0013 (17)	0.024 (2)
C12	0.034 (2)	0.053 (3)	0.038 (2)	0.0024 (18)	−0.0001 (17)	0.025 (2)
C13	0.033 (2)	0.040 (2)	0.038 (2)	0.0016 (17)	0.0033 (17)	0.0197 (18)
C14	0.040 (2)	0.046 (2)	0.042 (2)	0.0023 (19)	0.0019 (18)	0.0239 (19)
C15	0.043 (2)	0.045 (2)	0.035 (2)	0.0045 (19)	0.0087 (18)	0.0229 (19)
C16	0.037 (2)	0.041 (2)	0.053 (2)	0.0013 (18)	0.0104 (19)	0.021 (2)
C17	0.035 (2)	0.047 (2)	0.043 (2)	−0.0004 (18)	−0.0020 (18)	0.024 (2)
C18	0.042 (2)	0.050 (2)	0.043 (2)	0.0035 (19)	0.0053 (18)	0.028 (2)
C19	0.036 (2)	0.053 (3)	0.040 (2)	−0.0028 (18)	−0.0071 (17)	0.028 (2)
C20	0.045 (2)	0.058 (3)	0.042 (2)	0.006 (2)	0.0016 (18)	0.023 (2)
C21	0.041 (2)	0.063 (3)	0.047 (3)	0.006 (2)	0.006 (2)	0.031 (2)
N4	0.071 (3)	0.063 (3)	0.077 (3)	0.016 (2)	0.001 (2)	0.028 (2)
O8	0.076 (2)	0.120 (3)	0.098 (3)	0.033 (2)	0.007 (2)	0.065 (2)
C22	0.074 (3)	0.078 (4)	0.088 (4)	0.023 (3)	0.018 (3)	0.041 (3)
C23	0.068 (3)	0.115 (5)	0.108 (4)	0.024 (3)	0.004 (3)	0.049 (4)
C24	0.173 (6)	0.114 (5)	0.068 (3)	0.044 (4)	0.001 (4)	0.026 (3)
N5	0.116 (4)	0.071 (3)	0.078 (3)	0.006 (3)	0.016 (3)	0.029 (2)
O9	0.136 (4)	0.180 (5)	0.177 (5)	0.054 (4)	0.030 (4)	0.059 (4)
C25	0.147 (5)	0.096 (5)	0.111 (5)	0.044 (5)	0.026 (5)	0.040 (4)
C26	0.184 (6)	0.117 (5)	0.082 (4)	−0.037 (5)	0.010 (4)	0.043 (4)
C27	0.131 (5)	0.082 (4)	0.117 (5)	0.008 (4)	0.034 (4)	0.025 (4)

Geometric parameters (Å, º)

N1—C1	1.322 (4)	C12—H12	0.9300
N1—C8	1.430 (4)	C13—C18	1.381 (4)
N1—C19	1.473 (4)	C13—C14	1.454 (4)
N2—O3	1.213 (4)	C14—C15	1.449 (4)
N2—O2	1.218 (4)	C15—C16	1.366 (4)
N2—C15	1.447 (4)	C16—C17	1.373 (4)
N3—O4	1.223 (4)	C16—H16	0.9300
N3—O5	1.229 (4)	C17—C18	1.375 (4)
N3—C17	1.443 (4)	C18—H18	0.9300
O1—C14	1.238 (4)	C19—C20	1.509 (5)
O6—C21	1.196 (4)	C19—H19A	0.9700
O7—C21	1.312 (5)	C19—H19B	0.9700
O7—H7A	0.8536	C20—C21	1.495 (5)
C1—C11	1.421 (4)	C20—H20A	0.9700
C1—C2	1.522 (4)	C20—H20B	0.9700
C2—C3	1.505 (4)	N4—C22	1.310 (5)
C2—C10	1.531 (5)	N4—C23	1.433 (5)
C2—C9	1.537 (5)	N4—C24	1.439 (5)
C3—C4	1.375 (4)	O8—C22	1.236 (5)
C3—C8	1.379 (4)	C22—H22	0.9300
C4—C5	1.376 (5)	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C6	1.385 (5)	C23—H23C	0.9600
C5—H5	0.9300	C24—H24A	0.9600
C6—C7	1.376 (4)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C7—C8	1.380 (4)	N5—C25	1.318 (7)
C7—H7	0.9300	N5—C26	1.428 (6)
C9—H9A	0.9600	N5—C27	1.435 (6)
C9—H9B	0.9600	O9—C25	1.215 (7)
C9—H9C	0.9600	C25—H25A	0.9300
C10—H10A	0.9600	C26—H26A	0.9600
C10—H10B	0.9600	C26—H26B	0.9600
C10—H10C	0.9600	C26—H26C	0.9600
C11—C12	1.342 (4)	C27—H27A	0.9600
C11—H11	0.9300	C27—H27B	0.9600
C12—C13	1.439 (4)	C27—H27C	0.9600
C1—N1—C8	111.0 (3)	C16—C15—C14	123.4 (3)
C1—N1—C19	127.7 (3)	N2—C15—C14	120.6 (3)
C8—N1—C19	121.2 (3)	C15—C16—C17	119.2 (3)
O3—N2—O2	121.8 (3)	C15—C16—H16	120.4
O3—N2—C15	118.5 (3)	C17—C16—H16	120.4
O2—N2—C15	119.5 (3)	C16—C17—C18	121.6 (3)
O4—N3—O5	122.1 (3)	C16—C17—N3	118.8 (3)
O4—N3—C17	118.9 (3)	C18—C17—N3	119.6 (3)
O5—N3—C17	119.0 (3)	C17—C18—C13	120.6 (3)
C21—O7—H7A	112.3	C17—C18—H18	119.7
N1—C1—C11	122.3 (3)	C13—C18—H18	119.7
N1—C1—C2	109.8 (3)	N1—C19—C20	109.2 (3)
C11—C1—C2	127.9 (3)	N1—C19—H19A	109.8
C3—C2—C1	101.0 (2)	C20—C19—H19A	109.8
C3—C2—C10	111.6 (3)	N1—C19—H19B	109.8
C1—C2—C10	114.1 (3)	C20—C19—H19B	109.8
C3—C2—C9	109.6 (3)	H19A—C19—H19B	108.3
C1—C2—C9	109.6 (3)	C21—C20—C19	111.7 (3)
C10—C2—C9	110.6 (3)	C21—C20—H20A	109.3
C4—C3—C8	119.2 (3)	C19—C20—H20A	109.3
C4—C3—C2	131.3 (3)	C21—C20—H20B	109.3
C8—C3—C2	109.5 (3)	C19—C20—H20B	109.3
C3—C4—C5	118.2 (3)	H20A—C20—H20B	107.9
C3—C4—H4	120.9	O6—C21—O7	123.5 (4)
C5—C4—H4	120.9	O6—C21—C20	124.9 (4)
C4—C5—C6	121.5 (3)	O7—C21—C20	111.5 (4)
C4—C5—H5	119.3	C22—N4—C23	120.3 (4)
C6—C5—H5	119.3	C22—N4—C24	121.1 (4)
C7—C6—C5	121.3 (3)	C23—N4—C24	118.4 (4)
C7—C6—H6	119.3	O8—C22—N4	124.2 (5)
C5—C6—H6	119.3	O8—C22—H22	117.9
C6—C7—C8	115.9 (3)	N4—C22—H22	117.9
C6—C7—H7	122.1	N4—C23—H23A	109.5
C8—C7—H7	122.1	N4—C23—H23B	109.5
C3—C8—C7	123.9 (3)	H23A—C23—H23B	109.5
C3—C8—N1	108.2 (3)	N4—C23—H23C	109.5
C7—C8—N1	127.9 (3)	H23A—C23—H23C	109.5
C2—C9—H9A	109.5	H23B—C23—H23C	109.5
C2—C9—H9B	109.5	N4—C24—H24A	109.5
H9A—C9—H9B	109.5	N4—C24—H24B	109.5
C2—C9—H9C	109.5	H24A—C24—H24B	109.5
H9A—C9—H9C	109.5	N4—C24—H24C	109.5
H9B—C9—H9C	109.5	H24A—C24—H24C	109.5
C2—C10—H10A	109.5	H24B—C24—H24C	109.5
C2—C10—H10B	109.5	C25—N5—C26	121.3 (5)
H10A—C10—H10B	109.5	C25—N5—C27	121.0 (5)
C2—C10—H10C	109.5	C26—N5—C27	117.4 (5)
H10A—C10—H10C	109.5	O9—C25—N5	126.5 (7)
H10B—C10—H10C	109.5	O9—C25—H25A	116.8
C12—C11—C1	125.1 (3)	N5—C25—H25A	116.8
C12—C11—H11	117.4	N5—C26—H26A	109.5
C1—C11—H11	117.4	N5—C26—H26B	109.5
C11—C12—C13	126.9 (3)	H26A—C26—H26B	109.5
C11—C12—H12	116.6	N5—C26—H26C	109.5
C13—C12—H12	116.6	H26A—C26—H26C	109.5
C18—C13—C12	122.5 (3)	H26B—C26—H26C	109.5
C18—C13—C14	121.1 (3)	N5—C27—H27A	109.5
C12—C13—C14	116.3 (3)	N5—C27—H27B	109.5
O1—C14—C15	124.1 (3)	H27A—C27—H27B	109.5
O1—C14—C13	122.0 (3)	N5—C27—H27C	109.5
C15—C14—C13	113.9 (3)	H27A—C27—H27C	109.5
C16—C15—N2	116.0 (3)	H27B—C27—H27C	109.5
C8—N1—C1—C11	−174.4 (3)	C11—C12—C13—C14	−176.0 (4)
C19—N1—C1—C11	9.0 (5)	C18—C13—C14—O1	175.1 (3)
C8—N1—C1—C2	5.0 (4)	C12—C13—C14—O1	−3.4 (5)
C19—N1—C1—C2	−171.6 (3)	C18—C13—C14—C15	−3.8 (5)
N1—C1—C2—C3	−6.7 (4)	C12—C13—C14—C15	177.8 (3)
C11—C1—C2—C3	172.7 (3)	O3—N2—C15—C16	21.2 (5)
N1—C1—C2—C10	−126.5 (3)	O2—N2—C15—C16	−153.6 (3)
C11—C1—C2—C10	52.8 (5)	O3—N2—C15—C14	−158.6 (4)
N1—C1—C2—C9	108.9 (3)	O2—N2—C15—C14	26.6 (5)
C11—C1—C2—C9	−71.7 (4)	O1—C14—C15—C16	−174.2 (3)
C1—C2—C3—C4	−174.2 (4)	C13—C14—C15—C16	4.6 (5)
C10—C2—C3—C4	−52.5 (5)	O1—C14—C15—N2	5.6 (6)
C9—C2—C3—C4	70.3 (5)	C13—C14—C15—N2	−175.6 (3)
C1—C2—C3—C8	6.0 (4)	N2—C15—C16—C17	177.2 (3)
C10—C2—C3—C8	127.7 (3)	C14—C15—C16—C17	−3.0 (5)
C9—C2—C3—C8	−109.5 (3)	C15—C16—C17—C18	0.2 (5)
C8—C3—C4—C5	−0.5 (5)	C15—C16—C17—N3	179.9 (3)
C2—C3—C4—C5	179.7 (4)	O4—N3—C17—C16	0.4 (5)
C3—C4—C5—C6	1.6 (6)	O5—N3—C17—C16	−179.7 (4)
C4—C5—C6—C7	−1.5 (6)	O4—N3—C17—C18	−179.9 (4)
C5—C6—C7—C8	0.2 (5)	O5—N3—C17—C18	0.0 (5)
C4—C3—C8—C7	−0.8 (6)	C16—C17—C18—C13	0.5 (5)
C2—C3—C8—C7	179.0 (3)	N3—C17—C18—C13	−179.2 (3)
C4—C3—C8—N1	176.6 (3)	C12—C13—C18—C17	179.8 (3)
C2—C3—C8—N1	−3.6 (4)	C14—C13—C18—C17	1.5 (5)
C6—C7—C8—C3	0.9 (6)	C1—N1—C19—C20	95.8 (4)
C6—C7—C8—N1	−175.9 (3)	C8—N1—C19—C20	−80.5 (4)
C1—N1—C8—C3	−1.0 (4)	N1—C19—C20—C21	−173.4 (3)
C19—N1—C8—C3	175.9 (3)	C19—C20—C21—O6	9.3 (5)
C1—N1—C8—C7	176.3 (4)	C19—C20—C21—O7	−171.8 (3)
C19—N1—C8—C7	−6.8 (5)	C23—N4—C22—O8	2.5 (7)
N1—C1—C11—C12	−176.2 (3)	C24—N4—C22—O8	176.8 (5)
C2—C1—C11—C12	4.6 (6)	C26—N5—C25—O9	0.9 (10)
C1—C11—C12—C13	−176.4 (3)	C27—N5—C25—O9	174.0 (7)
C11—C12—C13—C18	5.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O8	0.85	1.71	2.560 (5)	173
C4—H4···O1^i	0.93	2.46	3.348 (5)	159
C4—H4···O2^i	0.93	2.47	3.175 (5)	133
C20—H20A···O3^ii	0.97	2.40	3.345 (5)	166
C7—H7···O5^iii	0.93	2.58	3.501 (5)	173
C11—H11···O6^iii	0.93	2.55	3.305 (4)	139
C18—H18···O6^iii	0.93	2.55	3.401 (4)	152
C26—H26A···O3	0.96	2.54	3.319 (8)	138

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