Crystal structure of diethyl 3,3′-[(4-nitro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate)

In the title compound, the two indole ring systems are approximately perpendicular to one another, making a dihedral angle of 89.7 (5)°. In the crystal, pairs of N—H...O hydrogen bonds link the mol­ecules into the inversion dimers, which are further linked into supra­molecular chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.164
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1  C   Ueq(max)/Ueq(min) Range         3.3 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C17      - C18      .       1.41 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     15.990 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.689 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2017 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Diethyl 3,3'-[(4-nitrophenyl)methylene]bis(1H-indole-2-carboxylate)

Crystal data

C29H25N3O6	F(000) = 1072
Mr = 511.52	Dx = 1.353 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.8040 (18) Å	θ = 9–13°
b = 15.804 (3) Å	µ = 0.10 mm^−1
c = 18.266 (4) Å	T = 293 K
β = 98.78 (3)°	Block, colorless
V = 2511.7 (9) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Nonius CAD-4 diffractometer	2963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.972, Tmax = 0.991	l = −22→22
4925 measured reflections	3 standard reflections every 200 reflections
4611 independent reflections	intensity decay: 1%

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.098P)^2] where P = (Fo^2 + 2Fc^2)/3
4611 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.3019 (3)	0.33359 (18)	0.86721 (14)	0.0648 (7)
C1	0.5958 (3)	0.31146 (14)	0.60845 (12)	0.0395 (5)
H1A	0.5204	0.3259	0.5650	0.047*
O1	0.3145 (3)	0.27719 (17)	0.91181 (14)	0.1013 (9)
N2	0.8861 (2)	0.47555 (13)	0.58612 (12)	0.0517 (6)
H2A	0.9392	0.5055	0.5600	0.062*
C2	0.5083 (3)	0.31093 (14)	0.67433 (13)	0.0394 (6)
O2	0.2403 (4)	0.39980 (19)	0.87776 (15)	0.1199 (11)
N3	0.6690 (2)	0.09119 (12)	0.55132 (10)	0.0435 (5)
H3A	0.6407	0.0442	0.5296	0.052*
O3	0.8106 (2)	0.45055 (14)	0.43699 (10)	0.0729 (6)
C3	0.4078 (3)	0.37605 (17)	0.68231 (14)	0.0546 (7)
H3B	0.3864	0.4157	0.6445	0.065*
O4	0.6050 (2)	0.37421 (13)	0.45415 (9)	0.0626 (5)
C4	0.3383 (3)	0.38418 (18)	0.74445 (15)	0.0590 (7)
H4A	0.2725	0.4291	0.7494	0.071*
O5	0.3605 (2)	0.08873 (11)	0.49279 (11)	0.0597 (5)
C5	0.3687 (3)	0.32430 (16)	0.79870 (14)	0.0485 (6)
O6	0.33771 (19)	0.22355 (10)	0.52526 (10)	0.0544 (5)
C6	0.4600 (3)	0.25512 (16)	0.79184 (14)	0.0488 (6)
H6A	0.4746	0.2137	0.8284	0.059*
C7	0.5301 (3)	0.24868 (15)	0.72855 (13)	0.0453 (6)
H7A	0.5920	0.2023	0.7226	0.054*
C8	0.7142 (3)	0.38043 (14)	0.61580 (13)	0.0413 (6)
C9	0.7960 (3)	0.41747 (15)	0.68231 (14)	0.0452 (6)
C10	0.7929 (3)	0.40819 (18)	0.75905 (14)	0.0569 (7)
H10A	0.7264	0.3696	0.7760	0.068*
C11	0.8885 (3)	0.45645 (19)	0.80769 (16)	0.0653 (8)
H11A	0.8854	0.4506	0.8581	0.078*
C12	0.9902 (3)	0.51407 (18)	0.78475 (16)	0.0610 (8)
H12A	1.0526	0.5464	0.8198	0.073*
C13	0.9999 (3)	0.52399 (16)	0.71204 (16)	0.0553 (7)
H13A	1.0699	0.5616	0.6966	0.066*
C14	0.9023 (3)	0.47627 (15)	0.66117 (14)	0.0479 (6)
C15	0.7728 (3)	0.42011 (15)	0.55827 (13)	0.0437 (6)
C16	0.7342 (3)	0.41604 (17)	0.47798 (15)	0.0518 (7)
C17	0.5564 (4)	0.3709 (3)	0.37461 (16)	0.0888 (11)
H17A	0.5529	0.4278	0.3545	0.107*
H17B	0.6304	0.3386	0.3519	0.107*
C18	0.4103 (5)	0.3332 (3)	0.3575 (2)	0.1267 (17)
H18A	0.3794	0.3330	0.3048	0.190*
H18B	0.3372	0.3649	0.3804	0.190*
H18C	0.4147	0.2761	0.3757	0.190*
C19	0.6591 (3)	0.22443 (14)	0.59271 (12)	0.0384 (5)
C20	0.8111 (3)	0.19214 (15)	0.61572 (13)	0.0431 (6)
C21	0.9467 (3)	0.22243 (18)	0.65751 (15)	0.0549 (7)
H21A	0.9506	0.2768	0.6771	0.066*
C22	1.0729 (3)	0.1716 (2)	0.66927 (17)	0.0656 (8)
H22A	1.1630	0.1920	0.6968	0.079*
C23	1.0702 (3)	0.0891 (2)	0.64087 (18)	0.0699 (9)
H23A	1.1584	0.0560	0.6499	0.084*
C24	0.9407 (3)	0.05644 (18)	0.60030 (16)	0.0593 (7)
H24A	0.9387	0.0017	0.5816	0.071*
C25	0.8115 (3)	0.10832 (16)	0.58803 (13)	0.0444 (6)
C26	0.5775 (3)	0.16072 (15)	0.55434 (12)	0.0414 (6)
C27	0.4159 (3)	0.15280 (15)	0.52078 (13)	0.0415 (6)
C28	0.1776 (3)	0.22520 (18)	0.49292 (16)	0.0582 (7)
H28A	0.1201	0.1837	0.5166	0.070*
H28B	0.1661	0.2126	0.4404	0.070*
C29	0.1216 (4)	0.3115 (2)	0.5050 (2)	0.0800 (10)
H29A	0.0149	0.3156	0.4843	0.120*
H29B	0.1797	0.3518	0.4813	0.120*
H29C	0.1340	0.3230	0.5571	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0613 (15)	0.0828 (19)	0.0541 (15)	0.0045 (14)	0.0213 (12)	−0.0012 (14)
C1	0.0445 (13)	0.0358 (12)	0.0368 (13)	−0.0016 (11)	0.0023 (10)	−0.0019 (10)
O1	0.131 (2)	0.110 (2)	0.0739 (16)	0.0141 (17)	0.0519 (16)	0.0261 (15)
N2	0.0568 (13)	0.0472 (12)	0.0531 (14)	−0.0065 (11)	0.0147 (11)	0.0026 (10)
C2	0.0426 (13)	0.0351 (12)	0.0395 (13)	−0.0071 (10)	0.0026 (11)	−0.0042 (10)
O2	0.168 (3)	0.117 (2)	0.0915 (19)	0.057 (2)	0.0745 (19)	0.0109 (16)
N3	0.0516 (13)	0.0353 (11)	0.0438 (12)	−0.0017 (9)	0.0073 (10)	−0.0073 (9)
O3	0.0749 (14)	0.0936 (16)	0.0510 (12)	−0.0223 (12)	0.0125 (10)	0.0160 (11)
C3	0.0665 (18)	0.0512 (15)	0.0460 (16)	0.0097 (14)	0.0085 (13)	0.0022 (12)
O4	0.0659 (13)	0.0848 (14)	0.0364 (10)	−0.0177 (11)	0.0052 (9)	0.0009 (9)
C4	0.0647 (18)	0.0619 (17)	0.0528 (17)	0.0138 (15)	0.0168 (14)	−0.0025 (14)
O5	0.0555 (11)	0.0509 (11)	0.0695 (13)	−0.0054 (9)	−0.0010 (9)	−0.0194 (9)
C5	0.0477 (15)	0.0562 (15)	0.0428 (14)	−0.0033 (13)	0.0108 (12)	−0.0044 (12)
O6	0.0485 (11)	0.0417 (10)	0.0691 (13)	0.0012 (8)	−0.0038 (9)	−0.0040 (9)
C6	0.0537 (16)	0.0494 (14)	0.0436 (15)	−0.0069 (13)	0.0080 (12)	0.0046 (12)
C7	0.0471 (14)	0.0408 (13)	0.0480 (15)	0.0002 (11)	0.0077 (11)	−0.0013 (11)
C8	0.0485 (14)	0.0363 (12)	0.0395 (13)	−0.0006 (11)	0.0078 (11)	−0.0013 (10)
C9	0.0521 (15)	0.0362 (13)	0.0477 (15)	−0.0031 (11)	0.0093 (12)	−0.0071 (11)
C10	0.0652 (18)	0.0632 (17)	0.0424 (15)	−0.0160 (14)	0.0089 (13)	−0.0068 (13)
C11	0.0708 (19)	0.077 (2)	0.0483 (16)	−0.0150 (17)	0.0078 (14)	−0.0159 (15)
C12	0.0602 (18)	0.0591 (17)	0.0608 (19)	−0.0081 (14)	0.0005 (14)	−0.0220 (14)
C13	0.0510 (16)	0.0396 (14)	0.075 (2)	−0.0094 (12)	0.0088 (14)	−0.0102 (13)
C14	0.0500 (15)	0.0401 (13)	0.0537 (16)	0.0002 (12)	0.0079 (12)	−0.0026 (11)
C15	0.0494 (14)	0.0417 (13)	0.0406 (14)	−0.0012 (12)	0.0084 (11)	0.0007 (11)
C16	0.0536 (16)	0.0558 (16)	0.0466 (15)	−0.0012 (13)	0.0093 (13)	0.0070 (13)
C17	0.087 (2)	0.135 (3)	0.0402 (17)	−0.019 (2)	−0.0032 (16)	0.0002 (19)
C18	0.105 (3)	0.185 (5)	0.088 (3)	−0.040 (3)	0.004 (3)	−0.023 (3)
C19	0.0450 (14)	0.0379 (12)	0.0326 (12)	−0.0029 (11)	0.0066 (10)	−0.0029 (10)
C20	0.0454 (14)	0.0488 (14)	0.0355 (13)	0.0005 (12)	0.0073 (11)	0.0003 (11)
C21	0.0520 (16)	0.0590 (16)	0.0514 (16)	−0.0032 (14)	0.0003 (13)	−0.0079 (13)
C22	0.0505 (17)	0.075 (2)	0.068 (2)	−0.0010 (16)	−0.0007 (14)	−0.0014 (16)
C23	0.0517 (18)	0.076 (2)	0.080 (2)	0.0135 (16)	0.0053 (16)	0.0071 (17)
C24	0.0564 (17)	0.0507 (16)	0.0708 (19)	0.0089 (14)	0.0100 (15)	−0.0001 (14)
C25	0.0457 (14)	0.0463 (14)	0.0417 (14)	−0.0009 (12)	0.0081 (11)	0.0025 (11)
C26	0.0454 (14)	0.0472 (14)	0.0316 (12)	−0.0009 (11)	0.0060 (10)	0.0010 (10)
C27	0.0509 (15)	0.0385 (13)	0.0348 (13)	−0.0035 (12)	0.0057 (11)	−0.0028 (10)
C28	0.0465 (16)	0.0606 (17)	0.0643 (18)	−0.0006 (13)	−0.0016 (13)	−0.0003 (14)
C29	0.070 (2)	0.068 (2)	0.099 (3)	0.0182 (17)	0.0043 (19)	0.0002 (18)

Geometric parameters (Å, º)

N1—O1	1.201 (3)	C10—H10A	0.9300
N1—O2	1.208 (3)	C11—C12	1.386 (4)
N1—C5	1.469 (3)	C11—H11A	0.9300
C1—C8	1.500 (3)	C12—C13	1.353 (4)
C1—C2	1.524 (3)	C12—H12A	0.9300
C1—C19	1.528 (3)	C13—C14	1.388 (4)
C1—H1A	0.9800	C13—H13A	0.9300
N2—C14	1.356 (3)	C15—C16	1.455 (3)
N2—C15	1.366 (3)	C17—C18	1.408 (5)
N2—H2A	0.8600	C17—H17A	0.9700
C2—C3	1.380 (3)	C17—H17B	0.9700
C2—C7	1.388 (3)	C18—H18A	0.9600
N3—C25	1.356 (3)	C18—H18B	0.9600
N3—C26	1.369 (3)	C18—H18C	0.9600
N3—H3A	0.8600	C19—C26	1.367 (3)
O3—C16	1.210 (3)	C19—C20	1.434 (3)
C3—C4	1.375 (3)	C20—C21	1.399 (3)
C3—H3B	0.9300	C20—C25	1.418 (3)
O4—C16	1.330 (3)	C21—C22	1.361 (4)
O4—C17	1.452 (3)	C21—H21A	0.9300
C4—C5	1.367 (4)	C22—C23	1.402 (4)
C4—H4A	0.9300	C22—H22A	0.9300
O5—C27	1.204 (3)	C23—C24	1.363 (4)
C5—C6	1.374 (3)	C23—H23A	0.9300
O6—C27	1.322 (3)	C24—C25	1.392 (4)
O6—C28	1.443 (3)	C24—H24A	0.9300
C6—C7	1.395 (3)	C26—C27	1.465 (3)
C6—H6A	0.9300	C28—C29	1.478 (4)
C7—H7A	0.9300	C28—H28A	0.9700
C8—C15	1.389 (3)	C28—H28B	0.9700
C8—C9	1.439 (3)	C29—H29A	0.9600
C9—C14	1.414 (3)	C29—H29B	0.9600
C9—C10	1.414 (3)	C29—H29C	0.9600
C10—C11	1.360 (4)
O1—N1—O2	122.1 (3)	N2—C15—C16	116.7 (2)
O1—N1—C5	119.7 (3)	C8—C15—C16	133.3 (2)
O2—N1—C5	118.1 (3)	O3—C16—O4	123.4 (3)
C8—C1—C2	111.17 (18)	O3—C16—C15	122.5 (3)
C8—C1—C19	113.74 (19)	O4—C16—C15	114.1 (2)
C2—C1—C19	112.73 (18)	C18—C17—O4	110.9 (3)
C8—C1—H1A	106.2	C18—C17—H17A	109.5
C2—C1—H1A	106.2	O4—C17—H17A	109.5
C19—C1—H1A	106.2	C18—C17—H17B	109.5
C14—N2—C15	109.9 (2)	O4—C17—H17B	109.5
C14—N2—H2A	125.1	H17A—C17—H17B	108.0
C15—N2—H2A	125.1	C17—C18—H18A	109.5
C3—C2—C7	118.3 (2)	C17—C18—H18B	109.5
C3—C2—C1	119.3 (2)	H18A—C18—H18B	109.5
C7—C2—C1	122.4 (2)	C17—C18—H18C	109.5
C25—N3—C26	109.01 (19)	H18A—C18—H18C	109.5
C25—N3—H3A	125.5	H18B—C18—H18C	109.5
C26—N3—H3A	125.5	C26—C19—C20	106.4 (2)
C4—C3—C2	122.0 (2)	C26—C19—C1	125.5 (2)
C4—C3—H3B	119.0	C20—C19—C1	128.0 (2)
C2—C3—H3B	119.0	C21—C20—C25	117.8 (2)
C16—O4—C17	116.9 (2)	C21—C20—C19	135.9 (2)
C5—C4—C3	118.1 (3)	C25—C20—C19	106.3 (2)
C5—C4—H4A	121.0	C22—C21—C20	119.4 (3)
C3—C4—H4A	121.0	C22—C21—H21A	120.3
C4—C5—C6	122.5 (2)	C20—C21—H21A	120.3
C4—C5—N1	119.2 (2)	C21—C22—C23	121.6 (3)
C6—C5—N1	118.2 (2)	C21—C22—H22A	119.2
C27—O6—C28	118.4 (2)	C23—C22—H22A	119.2
C5—C6—C7	118.2 (2)	C24—C23—C22	121.3 (3)
C5—C6—H6A	120.9	C24—C23—H23A	119.4
C7—C6—H6A	120.9	C22—C23—H23A	119.4
C2—C7—C6	120.6 (2)	C23—C24—C25	117.4 (3)
C2—C7—H7A	119.7	C23—C24—H24A	121.3
C6—C7—H7A	119.7	C25—C24—H24A	121.3
C15—C8—C9	105.0 (2)	N3—C25—C24	129.3 (2)
C15—C8—C1	126.4 (2)	N3—C25—C20	108.1 (2)
C9—C8—C1	128.5 (2)	C24—C25—C20	122.6 (2)
C14—C9—C10	116.9 (2)	C19—C26—N3	110.2 (2)
C14—C9—C8	107.7 (2)	C19—C26—C27	132.7 (2)
C10—C9—C8	135.4 (2)	N3—C26—C27	117.0 (2)
C11—C10—C9	119.0 (3)	O5—C27—O6	123.8 (2)
C11—C10—H10A	120.5	O5—C27—C26	123.7 (2)
C9—C10—H10A	120.5	O6—C27—C26	112.5 (2)
C10—C11—C12	122.3 (3)	O6—C28—C29	106.4 (2)
C10—C11—H11A	118.8	O6—C28—H28A	110.4
C12—C11—H11A	118.8	C29—C28—H28A	110.4
C13—C12—C11	120.9 (3)	O6—C28—H28B	110.4
C13—C12—H12A	119.5	C29—C28—H28B	110.4
C11—C12—H12A	119.5	H28A—C28—H28B	108.6
C12—C13—C14	117.9 (3)	C28—C29—H29A	109.5
C12—C13—H13A	121.0	C28—C29—H29B	109.5
C14—C13—H13A	121.0	H29A—C29—H29B	109.5
N2—C14—C13	129.8 (2)	C28—C29—H29C	109.5
N2—C14—C9	107.4 (2)	H29A—C29—H29C	109.5
C13—C14—C9	122.8 (2)	H29B—C29—H29C	109.5
N2—C15—C8	110.0 (2)
C8—C1—C2—C3	69.9 (3)	C9—C8—C15—C16	−175.6 (3)
C19—C1—C2—C3	−161.1 (2)	C1—C8—C15—C16	6.7 (4)
C8—C1—C2—C7	−107.7 (2)	C17—O4—C16—O3	0.0 (4)
C19—C1—C2—C7	21.4 (3)	C17—O4—C16—C15	177.5 (3)
C7—C2—C3—C4	4.9 (4)	N2—C15—C16—O3	9.9 (4)
C1—C2—C3—C4	−172.8 (2)	C8—C15—C16—O3	−172.8 (3)
C2—C3—C4—C5	−1.4 (4)	N2—C15—C16—O4	−167.6 (2)
C3—C4—C5—C6	−2.9 (4)	C8—C15—C16—O4	9.8 (4)
C3—C4—C5—N1	177.1 (2)	C16—O4—C17—C18	−173.4 (3)
O1—N1—C5—C4	172.3 (3)	C8—C1—C19—C26	−150.9 (2)
O2—N1—C5—C4	−10.4 (4)	C2—C1—C19—C26	81.3 (3)
O1—N1—C5—C6	−7.7 (4)	C8—C1—C19—C20	30.6 (3)
O2—N1—C5—C6	169.7 (3)	C2—C1—C19—C20	−97.1 (3)
C4—C5—C6—C7	3.4 (4)	C26—C19—C20—C21	−177.8 (3)
N1—C5—C6—C7	−176.6 (2)	C1—C19—C20—C21	0.9 (4)
C3—C2—C7—C6	−4.3 (4)	C26—C19—C20—C25	0.6 (2)
C1—C2—C7—C6	173.3 (2)	C1—C19—C20—C25	179.3 (2)
C5—C6—C7—C2	0.3 (4)	C25—C20—C21—C22	0.7 (4)
C2—C1—C8—C15	−154.3 (2)	C19—C20—C21—C22	179.0 (3)
C19—C1—C8—C15	77.2 (3)	C20—C21—C22—C23	−0.4 (4)
C2—C1—C8—C9	28.5 (3)	C21—C22—C23—C24	−0.1 (5)
C19—C1—C8—C9	−100.0 (3)	C22—C23—C24—C25	0.2 (4)
C15—C8—C9—C14	−1.3 (3)	C26—N3—C25—C24	178.9 (2)
C1—C8—C9—C14	176.3 (2)	C26—N3—C25—C20	0.1 (3)
C15—C8—C9—C10	178.7 (3)	C23—C24—C25—N3	−178.5 (3)
C1—C8—C9—C10	−3.7 (5)	C23—C24—C25—C20	0.2 (4)
C14—C9—C10—C11	1.1 (4)	C21—C20—C25—N3	178.3 (2)
C8—C9—C10—C11	−178.8 (3)	C19—C20—C25—N3	−0.4 (3)
C9—C10—C11—C12	−0.6 (4)	C21—C20—C25—C24	−0.6 (4)
C10—C11—C12—C13	−0.8 (5)	C19—C20—C25—C24	−179.4 (2)
C11—C12—C13—C14	1.6 (4)	C20—C19—C26—N3	−0.6 (3)
C15—N2—C14—C13	−178.3 (2)	C1—C19—C26—N3	−179.29 (19)
C15—N2—C14—C9	1.0 (3)	C20—C19—C26—C27	176.1 (2)
C12—C13—C14—N2	178.2 (3)	C1—C19—C26—C27	−2.6 (4)
C12—C13—C14—C9	−1.0 (4)	C25—N3—C26—C19	0.3 (3)
C10—C9—C14—N2	−179.8 (2)	C25—N3—C26—C27	−176.9 (2)
C8—C9—C14—N2	0.2 (3)	C28—O6—C27—O5	−1.9 (4)
C10—C9—C14—C13	−0.4 (4)	C28—O6—C27—C26	178.7 (2)
C8—C9—C14—C13	179.6 (2)	C19—C26—C27—O5	−174.8 (3)
C14—N2—C15—C8	−1.9 (3)	N3—C26—C27—O5	1.7 (3)
C14—N2—C15—C16	176.1 (2)	C19—C26—C27—O6	4.6 (4)
C9—C8—C15—N2	1.9 (3)	N3—C26—C27—O6	−178.84 (19)
C1—C8—C15—N2	−175.8 (2)	C27—O6—C28—C29	−179.0 (2)

Hydrogen-bond geometry (Å, º)

Cg1, Cg3 and Cg5 are the centroids of the N2/C8/C9/C14/C15 pyrrole, C2–C7 benzene and C21–C26 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3^i	0.86	2.30	3.003 (3)	139
N3—H3A···O5^ii	0.86	2.14	2.956 (3)	158
C11—H11A···O5^iii	0.93	2.58	3.501 (4)	171
C17—H17B···O1^iv	0.97	2.58	3.261 (5)	128
C29—H29A···O1^v	0.96	2.51	3.281 (4)	137
C10—H10A···Cg3	0.93	2.69	3.431 (3)	138
C21—H21A···Cg1	0.93	2.88	3.570 (3)	132
C28—H28A···Cg5^vi	0.97	2.85	3.718 (3)	150

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