Crystal structure of diethyl 3,3′-[(2-fluoro­phen­yl)methyl­idene]bis­(1H-indole-2-carboxyl­ate)

In the title compound, the two indole ring systems are approximately perpendicular to one another, subtending a dihedral angle of 86.0 (5)°. In the crystal, pairs of N—H...O hydrogen bonds link the mol­ecules into the inversion dimers, which are further linked by N—H...O hydrogen bonds into supra­molecular chains propagated along the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.069
• wR factor = 0.186
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        5.0 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        6.2 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C9      ..        5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C27    --  C28     ..        6.2 s.u.
PLAT234_ALERT_4_C Large Hirshfeld Difference C11    --  C12     ..       0.16 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C24    -C29           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00483 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond   C11    -   C12    ..       1.40 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C29 H25 F N2 O4
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     25.969 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.804 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
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
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)       0.03 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2016 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

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

---

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'-[(2-fluorophenyl)methylidene]bis(1H-indole-2-carboxylate)

Crystal data

C29H25FN2O4	Z = 2
Mr = 484.51	F(000) = 508
Triclinic, P1	Dx = 1.281 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8000 (18) Å	Cell parameters from 25 reflections
b = 9.6610 (19) Å	θ = 9–12°
c = 15.369 (3) Å	µ = 0.09 mm^−1
α = 75.68 (3)°	T = 293 K
β = 85.44 (3)°	Block, colorless
γ = 83.68 (3)°	0.30 × 0.20 × 0.10 mm
V = 1256.5 (4) Å^3

Data collection

Nonius CAD-4 diffractometer	2648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.973, Tmax = 0.991	l = −18→18
4947 measured reflections	3 standard reflections every 200 reflections
4621 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.090P)^2] where P = (Fo^2 + 2Fc^2)/3
4621 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.37 e Å^−3
2 restraints	Δρmin = −0.29 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
F	0.1008 (3)	1.1359 (3)	0.64799 (15)	0.0892 (8)
N1	−0.4074 (3)	1.1149 (3)	0.58021 (16)	0.0475 (7)
H1A	−0.4582	1.1074	0.5363	0.057*
O1	−0.3400 (3)	0.8585 (3)	0.53292 (16)	0.0649 (7)
C1	−0.1205 (3)	0.9767 (3)	0.75362 (18)	0.0355 (7)
H1B	−0.0473	0.9276	0.7172	0.043*
N2	−0.1865 (3)	0.6560 (3)	0.93763 (16)	0.0444 (7)
H2A	−0.1563	0.5744	0.9718	0.053*
O2	−0.1486 (3)	0.7970 (3)	0.62507 (17)	0.0638 (7)
C2	−0.2422 (3)	1.0600 (3)	0.69080 (18)	0.0380 (7)
O3	0.1216 (3)	0.5759 (2)	0.90831 (16)	0.0634 (7)
C3	−0.3183 (4)	1.1998 (3)	0.68783 (19)	0.0417 (8)
O4	0.1394 (2)	0.7613 (2)	0.79087 (14)	0.0507 (6)
C4	−0.3137 (4)	1.3049 (3)	0.7359 (2)	0.0529 (9)
H4A	−0.2488	1.2893	0.7830	0.064*
C5	−0.4062 (4)	1.4314 (4)	0.7129 (2)	0.0606 (10)
H5A	−0.4018	1.5015	0.7443	0.073*
C6	−0.5063 (4)	1.4570 (4)	0.6435 (2)	0.0605 (10)
H6A	−0.5680	1.5433	0.6299	0.073*
C7	−0.5152 (4)	1.3575 (4)	0.5952 (2)	0.0551 (9)
H7A	−0.5813	1.3751	0.5486	0.066*
C8	−0.4223 (4)	1.2284 (4)	0.6177 (2)	0.0467 (8)
C9	−0.2988 (3)	1.0132 (3)	0.62295 (19)	0.0393 (7)
C10	−0.2664 (4)	0.8840 (4)	0.5891 (2)	0.0467 (8)
C11	−0.1055 (5)	0.6707 (4)	0.5897 (3)	0.0861 (14)
H11A	−0.1634	0.5930	0.6234	0.103*
H11B	−0.1327	0.6921	0.5275	0.103*
C12	0.0510 (7)	0.6258 (8)	0.5943 (5)	0.178 (3)
H12A	0.0736	0.5438	0.5691	0.267*
H12B	0.0778	0.6005	0.6559	0.267*
H12C	0.1089	0.7021	0.5609	0.267*
C13	−0.1830 (3)	0.8604 (3)	0.82871 (18)	0.0353 (7)
C14	−0.3323 (3)	0.8555 (3)	0.8754 (2)	0.0405 (8)
C15	−0.4693 (4)	0.9485 (4)	0.8693 (2)	0.0479 (8)
H15A	−0.4763	1.0351	0.8261	0.057*
C16	−0.5897 (4)	0.9099 (4)	0.9272 (2)	0.0622 (10)
H16A	−0.6795	0.9711	0.9231	0.075*
C17	−0.5836 (4)	0.7812 (4)	0.9929 (2)	0.0620 (10)
H17A	−0.6685	0.7585	1.0318	0.074*
C18	−0.4548 (4)	0.6886 (4)	1.0008 (2)	0.0528 (9)
H18A	−0.4508	0.6023	1.0442	0.063*
C19	−0.3295 (4)	0.7259 (3)	0.9426 (2)	0.0422 (8)
C20	−0.0989 (3)	0.7352 (3)	0.87031 (19)	0.0376 (7)
C21	0.0629 (4)	0.6816 (3)	0.8594 (2)	0.0418 (8)
C22	0.2998 (4)	0.7133 (4)	0.7765 (2)	0.0571 (10)
H22A	0.3098	0.6184	0.7649	0.069*
H22B	0.3553	0.7094	0.8293	0.069*
C23	0.3614 (5)	0.8187 (5)	0.6976 (3)	0.0827 (13)
H23A	0.4676	0.7904	0.6858	0.124*
H23B	0.3513	0.9120	0.7100	0.124*
H23C	0.3053	0.8218	0.6460	0.124*
C24	−0.0307 (3)	1.0737 (3)	0.7890 (2)	0.0382 (7)
C25	−0.0470 (4)	1.0918 (3)	0.8758 (2)	0.0465 (8)
H25A	−0.1161	1.0400	0.9167	0.056*
C26	0.0363 (5)	1.1848 (4)	0.9036 (3)	0.0654 (11)
H26A	0.0206	1.1967	0.9620	0.078*
C27	0.1401 (5)	1.2582 (4)	0.8465 (3)	0.0695 (11)
H27A	0.1957	1.3209	0.8654	0.083*
C28	0.1636 (5)	1.2406 (4)	0.7610 (3)	0.0780 (12)
H28A	0.2370	1.2889	0.7216	0.094*
C29	0.0772 (4)	1.1507 (4)	0.7339 (2)	0.0564 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.111 (2)	0.0973 (18)	0.0577 (14)	−0.0417 (15)	0.0308 (13)	−0.0126 (13)
N1	0.0534 (18)	0.0491 (17)	0.0401 (15)	−0.0023 (14)	−0.0122 (13)	−0.0089 (13)
O1	0.0653 (16)	0.0822 (19)	0.0573 (15)	0.0048 (14)	−0.0190 (13)	−0.0360 (14)
C1	0.0391 (17)	0.0353 (16)	0.0296 (15)	0.0022 (14)	−0.0054 (13)	−0.0046 (13)
N2	0.0459 (16)	0.0382 (15)	0.0412 (15)	0.0039 (13)	−0.0051 (13)	0.0028 (12)
O2	0.0672 (17)	0.0560 (15)	0.0732 (17)	0.0115 (13)	−0.0284 (14)	−0.0253 (13)
C2	0.0433 (18)	0.0373 (17)	0.0297 (16)	−0.0008 (14)	−0.0064 (14)	−0.0011 (13)
O3	0.0520 (15)	0.0496 (14)	0.0694 (16)	0.0128 (12)	−0.0009 (13)	0.0132 (12)
C3	0.0471 (19)	0.0410 (18)	0.0325 (16)	0.0018 (15)	−0.0026 (14)	−0.0030 (14)
O4	0.0452 (14)	0.0510 (14)	0.0462 (13)	0.0065 (11)	0.0017 (11)	0.0003 (11)
C4	0.063 (2)	0.047 (2)	0.0464 (19)	0.0075 (18)	−0.0100 (17)	−0.0090 (16)
C5	0.075 (3)	0.044 (2)	0.060 (2)	0.0071 (19)	−0.009 (2)	−0.0092 (17)
C6	0.062 (3)	0.049 (2)	0.060 (2)	0.0139 (18)	−0.001 (2)	−0.0031 (19)
C7	0.049 (2)	0.057 (2)	0.048 (2)	0.0079 (18)	−0.0100 (17)	0.0050 (18)
C8	0.047 (2)	0.047 (2)	0.0386 (18)	0.0018 (16)	−0.0059 (15)	0.0017 (15)
C9	0.0410 (18)	0.0382 (17)	0.0355 (17)	0.0015 (14)	−0.0061 (14)	−0.0039 (14)
C10	0.047 (2)	0.055 (2)	0.0384 (18)	−0.0085 (17)	−0.0013 (16)	−0.0107 (16)
C11	0.098 (4)	0.056 (3)	0.116 (4)	0.008 (2)	−0.022 (3)	−0.044 (3)
C12	0.137 (6)	0.164 (7)	0.272 (10)	0.044 (5)	−0.060 (6)	−0.135 (7)
C13	0.0357 (17)	0.0361 (17)	0.0333 (16)	−0.0020 (13)	−0.0032 (13)	−0.0072 (13)
C14	0.0410 (19)	0.0422 (18)	0.0381 (17)	−0.0016 (15)	−0.0077 (15)	−0.0082 (14)
C15	0.0401 (19)	0.047 (2)	0.051 (2)	0.0038 (16)	−0.0063 (16)	−0.0036 (16)
C16	0.043 (2)	0.068 (3)	0.070 (3)	0.0091 (19)	0.0035 (19)	−0.014 (2)
C17	0.050 (2)	0.075 (3)	0.057 (2)	−0.009 (2)	0.0058 (18)	−0.010 (2)
C18	0.048 (2)	0.053 (2)	0.053 (2)	−0.0056 (18)	−0.0059 (17)	−0.0028 (17)
C19	0.0422 (19)	0.0435 (19)	0.0398 (18)	−0.0041 (15)	−0.0044 (15)	−0.0071 (15)
C20	0.0380 (18)	0.0335 (17)	0.0381 (17)	−0.0039 (14)	−0.0022 (14)	−0.0024 (14)
C21	0.046 (2)	0.0375 (18)	0.0383 (18)	0.0026 (15)	−0.0074 (15)	−0.0039 (15)
C22	0.044 (2)	0.060 (2)	0.063 (2)	0.0032 (18)	0.0058 (18)	−0.0133 (19)
C23	0.065 (3)	0.091 (3)	0.084 (3)	−0.011 (2)	0.020 (2)	−0.013 (3)
C24	0.0384 (18)	0.0332 (16)	0.0377 (17)	0.0026 (14)	−0.0060 (14)	0.0000 (13)
C25	0.048 (2)	0.046 (2)	0.0441 (19)	−0.0018 (16)	−0.0078 (16)	−0.0071 (15)
C26	0.077 (3)	0.055 (2)	0.069 (3)	0.000 (2)	−0.025 (2)	−0.022 (2)
C27	0.066 (3)	0.062 (3)	0.082 (3)	−0.014 (2)	−0.016 (2)	−0.014 (2)
C28	0.066 (3)	0.064 (3)	0.097 (3)	−0.023 (2)	0.001 (3)	0.000 (2)
C29	0.062 (2)	0.057 (2)	0.049 (2)	−0.0120 (19)	−0.0008 (18)	−0.0093 (18)

Geometric parameters (Å, º)

F—C29	1.360 (4)	C12—H12A	0.9600
N1—C8	1.349 (4)	C12—H12B	0.9600
N1—C9	1.372 (4)	C12—H12C	0.9600
N1—H1A	0.8600	C13—C20	1.384 (4)
O1—C10	1.205 (4)	C13—C14	1.446 (4)
C1—C24	1.511 (4)	C14—C19	1.412 (4)
C1—C13	1.513 (4)	C14—C15	1.417 (4)
C1—C2	1.522 (4)	C15—C16	1.351 (4)
C1—H1B	0.9800	C15—H15A	0.9300
N2—C20	1.365 (4)	C16—C17	1.393 (5)
N2—C19	1.367 (4)	C16—H16A	0.9300
N2—H2A	0.8600	C17—C18	1.358 (5)
O2—C10	1.326 (4)	C17—H17A	0.9300
O2—C11	1.456 (4)	C18—C19	1.384 (4)
C2—C9	1.380 (4)	C18—H18A	0.9300
C2—C3	1.432 (4)	C20—C21	1.472 (4)
O3—C21	1.200 (3)	C22—C23	1.486 (5)
C3—C4	1.402 (4)	C22—H22A	0.9700
C3—C8	1.424 (4)	C22—H22B	0.9700
O4—C21	1.325 (4)	C23—H23A	0.9600
O4—C22	1.453 (4)	C23—H23B	0.9600
C4—C5	1.376 (4)	C23—H23C	0.9600
C4—H4A	0.9300	C24—C29	1.374 (4)
C5—C6	1.395 (5)	C24—C25	1.382 (4)
C5—H5A	0.9300	C25—C26	1.383 (5)
C6—C7	1.364 (5)	C25—H25A	0.9300
C6—H6A	0.9300	C26—C27	1.347 (5)
C7—C8	1.396 (4)	C26—H26A	0.9300
C7—H7A	0.9300	C27—C28	1.363 (6)
C9—C10	1.460 (4)	C27—H27A	0.9300
C11—C12	1.400 (6)	C28—C29	1.372 (5)
C11—H11A	0.9700	C28—H28A	0.9300
C11—H11B	0.9700
C8—N1—C9	109.5 (3)	C14—C13—C1	129.9 (3)
C8—N1—H1A	125.2	C19—C14—C15	117.5 (3)
C9—N1—H1A	125.2	C19—C14—C13	107.3 (3)
C24—C1—C13	111.8 (2)	C15—C14—C13	135.1 (3)
C24—C1—C2	112.5 (2)	C16—C15—C14	119.2 (3)
C13—C1—C2	113.1 (2)	C16—C15—H15A	120.4
C24—C1—H1B	106.3	C14—C15—H15A	120.4
C13—C1—H1B	106.3	C15—C16—C17	122.1 (3)
C2—C1—H1B	106.3	C15—C16—H16A	119.0
C20—N2—C19	109.8 (2)	C17—C16—H16A	119.0
C20—N2—H2A	125.1	C18—C17—C16	120.7 (3)
C19—N2—H2A	125.1	C18—C17—H17A	119.7
C10—O2—C11	116.5 (3)	C16—C17—H17A	119.7
C9—C2—C3	106.3 (3)	C17—C18—C19	118.4 (3)
C9—C2—C1	125.3 (3)	C17—C18—H18A	120.8
C3—C2—C1	128.4 (3)	C19—C18—H18A	120.8
C4—C3—C8	117.8 (3)	N2—C19—C18	130.4 (3)
C4—C3—C2	135.7 (3)	N2—C19—C14	107.4 (3)
C8—C3—C2	106.4 (3)	C18—C19—C14	122.2 (3)
C21—O4—C22	116.5 (2)	N2—C20—C13	110.1 (3)
C5—C4—C3	119.3 (3)	N2—C20—C21	117.4 (3)
C5—C4—H4A	120.3	C13—C20—C21	132.3 (3)
C3—C4—H4A	120.3	O3—C21—O4	122.5 (3)
C4—C5—C6	121.6 (4)	O3—C21—C20	123.4 (3)
C4—C5—H5A	119.2	O4—C21—C20	114.0 (3)
C6—C5—H5A	119.2	O4—C22—C23	107.0 (3)
C7—C6—C5	121.0 (3)	O4—C22—H22A	110.3
C7—C6—H6A	119.5	C23—C22—H22A	110.3
C5—C6—H6A	119.5	O4—C22—H22B	110.3
C6—C7—C8	118.2 (3)	C23—C22—H22B	110.3
C6—C7—H7A	120.9	H22A—C22—H22B	108.6
C8—C7—H7A	120.9	C22—C23—H23A	109.5
N1—C8—C7	129.9 (3)	C22—C23—H23B	109.5
N1—C8—C3	108.1 (3)	H23A—C23—H23B	109.5
C7—C8—C3	122.0 (3)	C22—C23—H23C	109.5
N1—C9—C2	109.7 (3)	H23A—C23—H23C	109.5
N1—C9—C10	116.5 (3)	H23B—C23—H23C	109.5
C2—C9—C10	133.9 (3)	C29—C24—C25	115.3 (3)
O1—C10—O2	122.7 (3)	C29—C24—C1	120.1 (3)
O1—C10—C9	123.0 (3)	C25—C24—C1	124.6 (3)
O2—C10—C9	114.3 (3)	C24—C25—C26	121.9 (3)
C12—C11—O2	112.8 (4)	C24—C25—H25A	119.1
C12—C11—H11A	109.0	C26—C25—H25A	119.1
O2—C11—H11A	109.0	C27—C26—C25	120.3 (4)
C12—C11—H11B	109.0	C27—C26—H26A	119.8
O2—C11—H11B	109.0	C25—C26—H26A	119.8
H11A—C11—H11B	107.8	C26—C27—C28	120.0 (4)
C11—C12—H12A	109.5	C26—C27—H27A	120.0
C11—C12—H12B	109.5	C28—C27—H27A	120.0
H12A—C12—H12B	109.5	C27—C28—C29	118.9 (4)
C11—C12—H12C	109.5	C27—C28—H28A	120.5
H12A—C12—H12C	109.5	C29—C28—H28A	120.5
H12B—C12—H12C	109.5	F—C29—C28	118.1 (4)
C20—C13—C14	105.4 (2)	F—C29—C24	118.3 (3)
C20—C13—C1	124.6 (3)	C28—C29—C24	123.6 (4)
C24—C1—C2—C9	153.2 (3)	C19—C14—C15—C16	0.0 (5)
C13—C1—C2—C9	−79.0 (4)	C13—C14—C15—C16	−178.2 (3)
C24—C1—C2—C3	−25.5 (4)	C14—C15—C16—C17	0.0 (6)
C13—C1—C2—C3	102.3 (3)	C15—C16—C17—C18	−0.3 (6)
C9—C2—C3—C4	−179.3 (4)	C16—C17—C18—C19	0.6 (5)
C1—C2—C3—C4	−0.4 (6)	C20—N2—C19—C18	−178.6 (3)
C9—C2—C3—C8	1.5 (3)	C20—N2—C19—C14	−0.1 (3)
C1—C2—C3—C8	−179.6 (3)	C17—C18—C19—N2	177.7 (3)
C8—C3—C4—C5	−1.3 (5)	C17—C18—C19—C14	−0.6 (5)
C2—C3—C4—C5	179.5 (3)	C15—C14—C19—N2	−178.3 (3)
C3—C4—C5—C6	0.9 (5)	C13—C14—C19—N2	0.3 (3)
C4—C5—C6—C7	−0.6 (6)	C15—C14—C19—C18	0.3 (5)
C5—C6—C7—C8	0.6 (5)	C13—C14—C19—C18	178.9 (3)
C9—N1—C8—C7	178.2 (3)	C19—N2—C20—C13	−0.1 (4)
C9—N1—C8—C3	0.2 (4)	C19—N2—C20—C21	175.6 (3)
C6—C7—C8—N1	−178.8 (3)	C14—C13—C20—N2	0.3 (3)
C6—C7—C8—C3	−1.1 (5)	C1—C13—C20—N2	177.5 (3)
C4—C3—C8—N1	179.6 (3)	C14—C13—C20—C21	−174.5 (3)
C2—C3—C8—N1	−1.1 (4)	C1—C13—C20—C21	2.7 (5)
C4—C3—C8—C7	1.4 (5)	C22—O4—C21—O3	0.8 (5)
C2—C3—C8—C7	−179.2 (3)	C22—O4—C21—C20	−179.8 (3)
C8—N1—C9—C2	0.7 (4)	N2—C20—C21—O3	−2.8 (5)
C8—N1—C9—C10	−178.8 (3)	C13—C20—C21—O3	171.7 (3)
C3—C2—C9—N1	−1.4 (3)	N2—C20—C21—O4	177.8 (3)
C1—C2—C9—N1	179.7 (3)	C13—C20—C21—O4	−7.8 (5)
C3—C2—C9—C10	178.0 (3)	C21—O4—C22—C23	−179.5 (3)
C1—C2—C9—C10	−0.9 (5)	C13—C1—C24—C29	157.1 (3)
C11—O2—C10—O1	3.4 (5)	C2—C1—C24—C29	−74.4 (4)
C11—O2—C10—C9	−176.4 (3)	C13—C1—C24—C25	−22.3 (4)
N1—C9—C10—O1	−7.4 (5)	C2—C1—C24—C25	106.2 (3)
C2—C9—C10—O1	173.2 (3)	C29—C24—C25—C26	2.0 (5)
N1—C9—C10—O2	172.4 (3)	C1—C24—C25—C26	−178.5 (3)
C2—C9—C10—O2	−7.0 (5)	C24—C25—C26—C27	−1.8 (5)
C10—O2—C11—C12	150.0 (5)	C25—C26—C27—C28	−0.2 (6)
C24—C1—C13—C20	−80.3 (4)	C26—C27—C28—C29	1.8 (6)
C2—C1—C13—C20	151.4 (3)	C27—C28—C29—F	179.1 (3)
C24—C1—C13—C14	96.1 (3)	C27—C28—C29—C24	−1.5 (6)
C2—C1—C13—C14	−32.1 (4)	C25—C24—C29—F	179.0 (3)
C20—C13—C14—C19	−0.4 (3)	C1—C24—C29—F	−0.5 (5)
C1—C13—C14—C19	−177.3 (3)	C25—C24—C29—C28	−0.4 (5)
C20—C13—C14—C15	177.9 (3)	C1—C24—C29—C28	−179.8 (3)
C1—C13—C14—C15	1.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.10	2.881 (4)	151
N2—H2A···O3^ii	0.86	2.07	2.874 (3)	157

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