Diethyl 3,3′-[(3-fluoro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate)

In the title compound, C₂₉H₂₅FN₂O₄, the mean planes of the indole ring systems are approximately perpendicular to one another [dihedral angle = 88.3 (4)°]. The benzene ring is twisted with respect to the indole ring systems by 49.8 (5) and 77.6 (3)°. In the crystal, pairs of N—H...O hydrogen bonds link the mol­ecules into the inversion dimers which are further linked into supra­molecular chains propagating along the [110] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.143
• wR factor = 0.306
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low ..        30% Check
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.01559 Ang.
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check

Alert level C
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.715
            Test value =     -0.675
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.131
PLAT020_ALERT_3_C The Value of Rint is Greater Than 0.12 .........      0.131 Report
PLAT082_ALERT_2_C High R1 Value ..................................       0.14 Report
PLAT084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.31 Report
PLAT098_ALERT_2_C Large Reported Min.  (Negative) Residual Density      -0.71 eA-3
PLAT213_ALERT_2_C Atom C5              has ADP max/min Ratio .....        3.3 prolat
PLAT218_ALERT_3_C Constrained U(ij) Components(s) for C18        .          6 Check
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3       --C4       .        6.8 s.u.
PLAT234_ALERT_4_C Large Hirshfeld Difference F        --C6       .       0.21 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C2       --C7       .       0.21 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C5       --C6       .       0.25 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C6       --C7       .       0.24 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C9       --C14      .       0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C15      --C16      .       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C23      --C24      .       0.19 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C6 Check
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C17      - C18      .       1.37 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     17.711 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.015 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.056 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
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed 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/       2018 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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

Crystal data

C29H25FN2O4	F(000) = 1016
Mr = 484.51	Dx = 1.258 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.9960 (18) Å	Cell parameters from 25 reflections
b = 15.921 (3) Å	θ = 9–12°
c = 18.297 (4) Å	µ = 0.09 mm^−1
β = 102.59 (3)°	T = 293 K
V = 2557.6 (9) Å^3	Block, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1424 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.131
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 = 0.982, Tmax = 0.991	l = −22→21
5000 measured reflections	3 standard reflections every 200 reflections
4685 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)] = 0.143	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.306	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ^2(Fo^2) + (0.060P)^2] where P = (Fo^2 + 2Fc^2)/3
4685 reflections	(Δ/σ)max = 0.009
319 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.71 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.

H atoms were positioned geometrically with N—H = 0.86 Å and C—H = 0.93–0.98 Å, and constrained to ride on their parent atoms. The constraint U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(methyl C) was applied in all cases.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F	0.5574 (10)	0.2828 (5)	0.1783 (4)	0.154 (4)
O1	0.1733 (8)	0.0523 (4)	0.5601 (4)	0.080 (2)
N1	0.0972 (9)	0.0284 (4)	0.4084 (5)	0.063 (2)
H1A	0.0468	−0.0028	0.4327	0.076*
C1	0.3860 (9)	0.1906 (5)	0.3962 (5)	0.045 (2)
H1B	0.4561	0.1763	0.4434	0.054*
N2	0.3321 (8)	0.4124 (4)	0.4463 (4)	0.054 (2)
H2A	0.3634	0.4597	0.4668	0.064*
O2	0.3615 (8)	0.1390 (4)	0.5478 (4)	0.078 (2)
C2	0.4782 (11)	0.1845 (6)	0.3395 (6)	0.049 (3)
O3	0.6571 (7)	0.2781 (3)	0.4797 (3)	0.0609 (19)
C3	0.5727 (12)	0.1140 (8)	0.3428 (7)	0.094 (5)
H3A	0.5770	0.0753	0.3812	0.112*
O4	0.6412 (7)	0.4138 (4)	0.5044 (4)	0.071 (2)
C4	0.659 (2)	0.1009 (11)	0.2907 (12)	0.143 (7)
H4A	0.7197	0.0531	0.2945	0.172*
C5	0.6584 (19)	0.1558 (11)	0.2334 (11)	0.129 (7)
H5A	0.7151	0.1471	0.1972	0.155*
C6	0.5694 (16)	0.2231 (10)	0.2335 (7)	0.092 (4)
C7	0.4733 (12)	0.2417 (7)	0.2840 (6)	0.071 (3)
H7A	0.4121	0.2893	0.2792	0.086*
C8	0.2671 (10)	0.1236 (5)	0.3855 (6)	0.050 (3)
C9	0.1838 (10)	0.0882 (5)	0.3150 (6)	0.051 (3)
C10	0.1875 (12)	0.1021 (6)	0.2409 (7)	0.080 (4)
H10A	0.2524	0.1420	0.2276	0.096*
C11	0.0911 (12)	0.0547 (7)	0.1867 (6)	0.082 (4)
H11A	0.0929	0.0626	0.1366	0.099*
C12	−0.0061 (14)	−0.0033 (7)	0.2053 (7)	0.088 (4)
H12A	−0.0678	−0.0341	0.1673	0.105*
C13	−0.0162 (12)	−0.0175 (6)	0.2762 (7)	0.077 (3)
H13A	−0.0844	−0.0565	0.2878	0.092*
C14	0.0816 (11)	0.0295 (6)	0.3329 (7)	0.058 (3)
C15	0.2065 (11)	0.0855 (6)	0.4391 (6)	0.057 (3)
C16	0.2487 (12)	0.0887 (6)	0.5223 (7)	0.061 (3)
C17	0.4070 (12)	0.1489 (9)	0.6278 (6)	0.108 (5)
H17A	0.3662	0.2010	0.6427	0.129*
H17B	0.3673	0.1029	0.6525	0.129*
C18	0.5630 (13)	0.1500 (7)	0.6483 (7)	0.112
H18A	0.5940	0.1565	0.7016	0.168*
H18B	0.6015	0.1960	0.6241	0.168*
H18C	0.6027	0.0982	0.6337	0.168*
C19	0.3282 (9)	0.2778 (5)	0.4087 (5)	0.039 (2)
C20	0.1817 (11)	0.3129 (5)	0.3856 (5)	0.049 (3)
C21	0.0406 (12)	0.2819 (6)	0.3459 (6)	0.069 (3)
H21A	0.0315	0.2268	0.3286	0.082*
C22	−0.0847 (13)	0.3351 (7)	0.3330 (6)	0.077 (4)
H22A	−0.1789	0.3152	0.3073	0.092*
C23	−0.0710 (13)	0.4196 (7)	0.3585 (6)	0.089 (4)
H23A	−0.1560	0.4544	0.3490	0.106*
C24	0.0652 (12)	0.4502 (6)	0.3968 (6)	0.071 (3)
H24A	0.0749	0.5056	0.4131	0.085*
C25	0.1893 (11)	0.3958 (5)	0.4105 (5)	0.054 (3)
C26	0.4231 (11)	0.3414 (5)	0.4456 (5)	0.044 (2)
C27	0.5740 (11)	0.3489 (5)	0.4795 (5)	0.045 (2)
C28	0.8156 (10)	0.2802 (6)	0.5124 (6)	0.075 (3)
H28A	0.8324	0.2942	0.5651	0.089*
H28B	0.8662	0.3218	0.4877	0.089*
C29	0.8750 (12)	0.1962 (7)	0.5028 (6)	0.101 (4)
H29A	0.9824	0.1948	0.5241	0.152*
H29B	0.8573	0.1830	0.4504	0.152*
H29C	0.8242	0.1557	0.5276	0.152*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.256 (10)	0.129 (7)	0.088 (6)	−0.081 (7)	0.063 (6)	−0.033 (5)
O1	0.085 (6)	0.085 (5)	0.073 (6)	−0.020 (4)	0.022 (4)	0.013 (4)
N1	0.076 (6)	0.026 (4)	0.088 (7)	−0.012 (4)	0.016 (6)	−0.001 (5)
C1	0.050 (6)	0.033 (5)	0.053 (7)	−0.012 (5)	0.011 (5)	0.000 (5)
N2	0.058 (5)	0.031 (4)	0.065 (6)	−0.009 (4)	0.001 (5)	−0.015 (4)
O2	0.081 (5)	0.091 (6)	0.060 (5)	−0.032 (5)	0.014 (4)	−0.005 (4)
C2	0.057 (7)	0.035 (6)	0.065 (8)	−0.025 (5)	0.033 (6)	−0.021 (5)
O3	0.068 (5)	0.036 (4)	0.072 (5)	0.002 (4)	0.001 (4)	−0.004 (3)
C3	0.068 (8)	0.109 (11)	0.117 (12)	−0.005 (8)	0.049 (8)	−0.068 (9)
O4	0.079 (5)	0.030 (4)	0.093 (5)	−0.004 (4)	−0.008 (4)	−0.016 (4)
C4	0.132 (15)	0.105 (14)	0.18 (2)	−0.017 (12)	0.016 (15)	−0.038 (13)
C5	0.132 (14)	0.101 (13)	0.169 (19)	−0.033 (12)	0.065 (14)	−0.106 (13)
C6	0.113 (11)	0.097 (11)	0.066 (10)	−0.081 (9)	0.022 (9)	−0.013 (9)
C7	0.079 (8)	0.067 (8)	0.077 (9)	−0.039 (7)	0.036 (7)	−0.046 (7)
C8	0.062 (7)	0.025 (5)	0.061 (7)	−0.011 (5)	0.013 (6)	−0.002 (5)
C9	0.063 (7)	0.025 (5)	0.069 (8)	−0.017 (5)	0.023 (6)	−0.012 (6)
C10	0.104 (9)	0.053 (7)	0.077 (9)	−0.029 (6)	0.009 (8)	−0.024 (7)
C11	0.097 (9)	0.081 (8)	0.070 (9)	−0.023 (7)	0.021 (7)	−0.029 (7)
C12	0.105 (10)	0.074 (9)	0.084 (10)	−0.019 (8)	0.023 (9)	−0.040 (8)
C13	0.084 (8)	0.034 (6)	0.112 (10)	−0.010 (6)	0.019 (8)	−0.028 (7)
C14	0.063 (7)	0.032 (6)	0.076 (9)	0.006 (5)	0.006 (7)	−0.015 (6)
C15	0.069 (7)	0.031 (6)	0.067 (8)	0.007 (5)	0.010 (7)	−0.003 (6)
C16	0.053 (7)	0.039 (6)	0.094 (10)	−0.010 (6)	0.022 (7)	0.006 (6)
C17	0.062 (8)	0.200 (14)	0.058 (9)	−0.006 (8)	0.008 (7)	−0.030 (9)
C18	0.112	0.112	0.112	0.000	0.024	0.000
C19	0.041 (6)	0.026 (5)	0.049 (6)	−0.005 (4)	0.010 (5)	−0.006 (4)
C20	0.065 (7)	0.032 (5)	0.047 (6)	−0.009 (5)	0.008 (6)	−0.004 (5)
C21	0.072 (8)	0.042 (6)	0.085 (9)	−0.001 (6)	0.003 (7)	−0.010 (6)
C22	0.089 (9)	0.061 (8)	0.070 (8)	−0.002 (7)	−0.008 (7)	−0.015 (6)
C23	0.086 (9)	0.072 (8)	0.098 (10)	0.028 (7)	−0.002 (8)	−0.001 (8)
C24	0.068 (8)	0.039 (6)	0.097 (9)	−0.002 (6)	−0.003 (7)	−0.013 (6)
C25	0.054 (7)	0.036 (6)	0.063 (7)	−0.001 (5)	−0.007 (6)	0.004 (5)
C26	0.053 (6)	0.036 (5)	0.044 (6)	0.003 (5)	0.009 (5)	−0.001 (5)
C27	0.060 (7)	0.030 (5)	0.042 (6)	0.006 (5)	0.001 (5)	−0.008 (5)
C28	0.053 (7)	0.056 (7)	0.100 (9)	0.015 (6)	−0.016 (7)	0.001 (6)
C29	0.097 (9)	0.099 (9)	0.104 (10)	0.053 (8)	0.012 (8)	−0.007 (8)

Geometric parameters (Å, º)

F—C6	1.374 (13)	C11—C12	1.365 (13)
O1—C16	1.216 (10)	C11—H11A	0.9300
N1—C14	1.356 (11)	C12—C13	1.339 (13)
N1—C15	1.367 (10)	C12—H12A	0.9300
N1—H1A	0.8600	C13—C14	1.418 (12)
C1—C2	1.464 (11)	C13—H13A	0.9300
C1—C8	1.492 (10)	C15—C16	1.488 (13)
C1—C19	1.517 (10)	C17—C18	1.371 (12)
C1—H1B	0.9800	C17—H17A	0.9700
N2—C25	1.335 (10)	C17—H17B	0.9700
N2—C26	1.398 (9)	C18—H18A	0.9600
N2—H2A	0.8600	C18—H18B	0.9600
O2—C16	1.297 (10)	C18—H18C	0.9600
O2—C17	1.440 (11)	C19—C26	1.399 (10)
C2—C7	1.359 (13)	C19—C20	1.409 (11)
C2—C3	1.401 (13)	C20—C25	1.394 (11)
O3—C27	1.351 (9)	C20—C21	1.407 (11)
O3—C28	1.421 (9)	C21—C22	1.389 (12)
C3—C4	1.370 (18)	C21—H21A	0.9300
C3—H3A	0.9300	C22—C23	1.420 (12)
O4—C27	1.234 (9)	C22—H22A	0.9300
C4—C5	1.363 (19)	C23—C24	1.361 (12)
C4—H4A	0.9300	C23—H23A	0.9300
C5—C6	1.339 (18)	C24—C25	1.392 (11)
C5—H5A	0.9300	C24—H24A	0.9300
C6—C7	1.426 (15)	C26—C27	1.370 (11)
C7—H7A	0.9300	C28—C29	1.465 (11)
C8—C15	1.364 (11)	C28—H28A	0.9700
C8—C9	1.457 (12)	C28—H28B	0.9700
C9—C10	1.382 (12)	C29—H29A	0.9600
C9—C14	1.400 (11)	C29—H29B	0.9600
C10—C11	1.389 (12)	C29—H29C	0.9600
C10—H10A	0.9300
C14—N1—C15	108.4 (9)	C8—C15—C16	131.9 (10)
C14—N1—H1A	125.8	O1—C16—O2	125.4 (11)
C15—N1—H1A	125.8	O1—C16—C15	121.1 (10)
C2—C1—C8	111.1 (7)	O2—C16—C15	113.2 (10)
C2—C1—C19	115.7 (7)	C18—C17—O2	109.1 (10)
C8—C1—C19	114.4 (7)	C18—C17—H17A	109.9
C2—C1—H1B	104.7	O2—C17—H17A	109.9
C8—C1—H1B	104.7	C18—C17—H17B	109.9
C19—C1—H1B	104.7	O2—C17—H17B	109.9
C25—N2—C26	109.7 (7)	H17A—C17—H17B	108.3
C25—N2—H2A	125.1	C17—C18—H18A	109.5
C26—N2—H2A	125.1	C17—C18—H18B	109.5
C16—O2—C17	117.4 (9)	H18A—C18—H18B	109.5
C7—C2—C3	119.2 (11)	C17—C18—H18C	109.5
C7—C2—C1	123.7 (10)	H18A—C18—H18C	109.5
C3—C2—C1	117.1 (10)	H18B—C18—H18C	109.5
C27—O3—C28	119.0 (7)	C26—C19—C20	106.9 (7)
C4—C3—C2	121.6 (15)	C26—C19—C1	122.8 (8)
C4—C3—H3A	119.2	C20—C19—C1	130.2 (7)
C2—C3—H3A	119.2	C25—C20—C21	118.4 (9)
C3—C4—C5	122.0 (19)	C25—C20—C19	107.5 (8)
C3—C4—H4A	119.0	C21—C20—C19	134.1 (8)
C5—C4—H4A	119.0	C22—C21—C20	118.8 (9)
C6—C5—C4	114.4 (18)	C22—C21—H21A	120.6
C6—C5—H5A	122.8	C20—C21—H21A	120.6
C4—C5—H5A	122.8	C21—C22—C23	120.8 (10)
C5—C6—F	120.2 (17)	C21—C22—H22A	119.6
C5—C6—C7	127.9 (14)	C23—C22—H22A	119.6
F—C6—C7	111.8 (15)	C24—C23—C22	120.8 (10)
C2—C7—C6	114.8 (11)	C24—C23—H23A	119.6
C2—C7—H7A	122.6	C22—C23—H23A	119.6
C6—C7—H7A	122.6	C23—C24—C25	117.8 (9)
C15—C8—C9	104.8 (8)	C23—C24—H24A	121.1
C15—C8—C1	127.7 (9)	C25—C24—H24A	121.1
C9—C8—C1	127.4 (9)	N2—C25—C24	127.8 (9)
C10—C9—C14	119.6 (10)	N2—C25—C20	108.8 (8)
C10—C9—C8	133.6 (9)	C24—C25—C20	123.4 (9)
C14—C9—C8	106.8 (9)	C27—C26—N2	116.7 (8)
C11—C10—C9	117.9 (10)	C27—C26—C19	136.2 (8)
C11—C10—H10A	121.0	N2—C26—C19	107.1 (7)
C9—C10—H10A	121.0	O4—C27—O3	118.1 (8)
C12—C11—C10	121.6 (11)	O4—C27—C26	126.7 (8)
C12—C11—H11A	119.2	O3—C27—C26	114.9 (8)
C10—C11—H11A	119.2	O3—C28—C29	106.7 (8)
C13—C12—C11	122.5 (12)	O3—C28—H28A	110.4
C13—C12—H12A	118.7	C29—C28—H28A	110.4
C11—C12—H12A	118.7	O3—C28—H28B	110.4
C12—C13—C14	117.2 (11)	C29—C28—H28B	110.4
C12—C13—H13A	121.4	H28A—C28—H28B	108.6
C14—C13—H13A	121.4	C28—C29—H29A	109.5
N1—C14—C9	108.6 (9)	C28—C29—H29B	109.5
N1—C14—C13	130.4 (11)	H29A—C29—H29B	109.5
C9—C14—C13	121.0 (11)	C28—C29—H29C	109.5
N1—C15—C8	111.4 (9)	H29A—C29—H29C	109.5
N1—C15—C16	116.3 (10)	H29B—C29—H29C	109.5
C8—C1—C2—C7	110.8 (9)	C17—O2—C16—O1	3.8 (15)
C19—C1—C2—C7	−21.8 (13)	C17—O2—C16—C15	177.6 (9)
C8—C1—C2—C3	−67.4 (11)	N1—C15—C16—O1	−11.3 (14)
C19—C1—C2—C3	159.9 (8)	C8—C15—C16—O1	176.3 (10)
C7—C2—C3—C4	−0.8 (16)	N1—C15—C16—O2	174.6 (8)
C1—C2—C3—C4	177.5 (11)	C8—C15—C16—O2	2.1 (15)
C2—C3—C4—C5	1 (2)	C16—O2—C17—C18	138.6 (11)
C3—C4—C5—C6	1 (2)	C2—C1—C19—C26	−72.7 (11)
C4—C5—C6—F	−179.3 (12)	C8—C1—C19—C26	156.2 (8)
C4—C5—C6—C7	−3 (2)	C2—C1—C19—C20	104.3 (11)
C3—C2—C7—C6	−0.4 (13)	C8—C1—C19—C20	−26.8 (14)
C1—C2—C7—C6	−178.6 (8)	C26—C19—C20—C25	−1.7 (10)
C5—C6—C7—C2	2.2 (17)	C1—C19—C20—C25	−179.0 (9)
F—C6—C7—C2	179.2 (8)	C26—C19—C20—C21	179.0 (10)
C2—C1—C8—C15	149.4 (10)	C1—C19—C20—C21	1.6 (18)
C19—C1—C8—C15	−77.3 (12)	C25—C20—C21—C22	0.2 (15)
C2—C1—C8—C9	−34.5 (13)	C19—C20—C21—C22	179.5 (10)
C19—C1—C8—C9	98.8 (11)	C20—C21—C22—C23	0.8 (16)
C15—C8—C9—C10	177.8 (11)	C21—C22—C23—C24	−0.5 (18)
C1—C8—C9—C10	1.0 (17)	C22—C23—C24—C25	−0.6 (17)
C15—C8—C9—C14	−1.5 (10)	C26—N2—C25—C24	−177.8 (10)
C1—C8—C9—C14	−178.2 (8)	C26—N2—C25—C20	0.5 (11)
C14—C9—C10—C11	−1.9 (15)	C23—C24—C25—N2	179.7 (10)
C8—C9—C10—C11	178.9 (10)	C23—C24—C25—C20	1.7 (16)
C9—C10—C11—C12	0.9 (16)	C21—C20—C25—N2	−179.8 (8)
C10—C11—C12—C13	0.7 (19)	C19—C20—C25—N2	0.7 (11)
C11—C12—C13—C14	−1.2 (18)	C21—C20—C25—C24	−1.4 (15)
C15—N1—C14—C9	0.3 (10)	C19—C20—C25—C24	179.1 (9)
C15—N1—C14—C13	−179.8 (9)	C25—N2—C26—C27	179.2 (8)
C10—C9—C14—N1	−178.7 (9)	C25—N2—C26—C19	−1.5 (10)
C8—C9—C14—N1	0.7 (10)	C20—C19—C26—C27	−179.0 (11)
C10—C9—C14—C13	1.4 (14)	C1—C19—C26—C27	−1.4 (16)
C8—C9—C14—C13	−179.2 (8)	C20—C19—C26—N2	1.9 (10)
C12—C13—C14—N1	−179.8 (10)	C1—C19—C26—N2	179.5 (8)
C12—C13—C14—C9	0.1 (15)	C28—O3—C27—O4	3.8 (13)
C14—N1—C15—C8	−1.3 (11)	C28—O3—C27—C26	178.8 (8)
C14—N1—C15—C16	−175.3 (8)	N2—C26—C27—O4	−7.4 (14)
C9—C8—C15—N1	1.7 (10)	C19—C26—C27—O4	173.6 (10)
C1—C8—C15—N1	178.5 (8)	N2—C26—C27—O3	178.1 (7)
C9—C8—C15—C16	174.4 (9)	C19—C26—C27—O3	−1.0 (16)
C1—C8—C15—C16	−8.8 (16)	C27—O3—C28—C29	−178.8 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.16	2.918 (11)	147
N2—H2A···O4^ii	0.86	2.08	2.904 (9)	159
C11—H11A···O4^iii	0.93	2.58	3.498 (13)	171

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