1-n-Butyl-2-(4'-fluoro­phenyl)-1H-benz­imidazole-6-carbo­nitrile

The structure of the title compound, C₁₈H₁₆FN₃, consists of neutral mol­ecules. The asymmetric unit contains two independent mol­ecules with similar conformations: the dihedral angles between the benz­imidazole moiety and the benzene rings are 34.99 (9) and 36.08 (8)°. The crystal structure is stabilized by dipole-dipole and van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.083
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17     ..       6.02 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12    -   C14    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C29    -   C32    ...       1.45 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               3216
           Count of symmetry unique reflns         3216
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-n-Butyl-2-(4'-fluorophenyl)-1H-benzimidazole-6-carbonitrile

Crystal data

C18H16FN3	F(000) = 1232
Mr = 293.34	Dx = 1.224 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 15369 reflections
a = 18.0843 (5) Å	θ = 0.0–24.7°
b = 8.1980 (14) Å	µ = 0.08 mm^−1
c = 21.4690 (12) Å	T = 293 K
V = 3182.9 (6) Å^3	Needle, colourless
Z = 8	0.40 × 0.32 × 0.06 mm

Data collection

Stoe IPDS-2 diffractometer	1791 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.117
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
Detector resolution: 6.67 pixels mm^-1	h = −22→22
rotation method scans	k = −10→9
43476 measured reflections	l = −26→26
3216 independent reflections

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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0453P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
3216 reflections	Δρmax = 0.12 e Å^−3
398 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (7)

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
C1	0.3412 (2)	0.5615 (5)	0.40277 (18)	0.0909 (11)
C2	0.29766 (18)	0.5376 (4)	0.45344 (18)	0.0792 (10)
H2	0.2520	0.4861	0.4501	0.095*
C3	0.32353 (17)	0.5923 (4)	0.51020 (15)	0.0679 (8)
H3	0.2949	0.5776	0.5457	0.081*
C4	0.39113 (16)	0.6684 (3)	0.51491 (15)	0.0603 (7)
C5	0.43275 (19)	0.6911 (4)	0.46130 (16)	0.0781 (9)
H5	0.4783	0.7434	0.4638	0.094*
C6	0.4075 (2)	0.6375 (5)	0.40480 (18)	0.0959 (11)
H6	0.4353	0.6528	0.3688	0.115*
C7	0.42458 (16)	0.7184 (4)	0.57460 (15)	0.0602 (8)
C8	0.43849 (16)	0.8131 (3)	0.67057 (16)	0.0638 (8)
C9	0.50630 (17)	0.7679 (4)	0.64452 (14)	0.0653 (8)
C10	0.57082 (18)	0.7838 (4)	0.67894 (17)	0.0835 (10)
H10	0.6163	0.7526	0.6626	0.100*
C11	0.56518 (19)	0.8475 (5)	0.73818 (18)	0.0919 (11)
H11	0.6077	0.8616	0.7619	0.110*
C12	0.49732 (19)	0.8909 (4)	0.76282 (16)	0.0810 (10)
C13	0.43207 (17)	0.8765 (4)	0.72975 (17)	0.0740 (9)
H13	0.3867	0.9075	0.7464	0.089*
C14	0.4949 (3)	0.9546 (6)	0.8252 (2)	0.1018 (14)
C15	0.30898 (16)	0.8288 (3)	0.62937 (16)	0.0670 (8)
H15A	0.2888	0.8357	0.5876	0.080*
H15B	0.3068	0.9371	0.6474	0.080*
C16	0.26067 (16)	0.7175 (4)	0.66714 (17)	0.0720 (8)
H16A	0.2815	0.7030	0.7084	0.086*
H16B	0.2576	0.6114	0.6473	0.086*
C17	0.1839 (2)	0.7928 (6)	0.6720 (2)	0.1055 (13)
H17A	0.1879	0.8953	0.6943	0.127*
H17B	0.1663	0.8171	0.6304	0.127*
C18	0.1297 (2)	0.6926 (7)	0.7029 (3)	0.158 (2)
H18A	0.0831	0.7487	0.7038	0.236*
H18B	0.1456	0.6705	0.7447	0.236*
H18C	0.1242	0.5917	0.6807	0.236*
C19	0.3988 (2)	0.4066 (5)	0.78792 (18)	0.0909 (11)
C20	0.3320 (2)	0.3348 (5)	0.78398 (18)	0.0951 (12)
H20	0.3032	0.3197	0.8194	0.114*
C21	0.30728 (18)	0.2842 (4)	0.72655 (16)	0.0783 (9)
H21	0.2612	0.2346	0.7232	0.094*
C22	0.35040 (16)	0.3062 (3)	0.67339 (15)	0.0617 (8)
C23	0.41843 (18)	0.3805 (4)	0.67997 (16)	0.0722 (9)
H23	0.4482	0.3955	0.6451	0.087*
C24	0.4433 (2)	0.4332 (5)	0.7379 (2)	0.0850 (10)
H24	0.4888	0.4849	0.7423	0.102*
C25	0.31826 (16)	0.2571 (4)	0.61356 (15)	0.0604 (8)
C26	0.23740 (17)	0.2053 (4)	0.54360 (14)	0.0641 (8)
C27	0.17301 (17)	0.1892 (4)	0.50853 (16)	0.0743 (9)
H27	0.1276	0.2236	0.5240	0.089*
C28	0.1788 (2)	0.1208 (5)	0.45023 (17)	0.0853 (10)
H28	0.1367	0.1086	0.4258	0.102*
C29	0.2480 (2)	0.0687 (4)	0.42705 (16)	0.0771 (9)
C30	0.31247 (18)	0.0856 (4)	0.46036 (16)	0.0721 (9)
H30	0.3580	0.0526	0.4446	0.087*
C31	0.30538 (15)	0.1551 (3)	0.51898 (15)	0.0616 (7)
C32	0.2502 (3)	−0.0032 (5)	0.3654 (2)	0.0985 (13)
C33	0.43569 (15)	0.1455 (4)	0.55998 (16)	0.0648 (8)
H33A	0.4394	0.0385	0.5409	0.078*
H33B	0.4564	0.1378	0.6016	0.078*
C34	0.48100 (15)	0.2650 (4)	0.52244 (17)	0.0669 (8)
H34A	0.4597	0.2768	0.4812	0.080*
H34B	0.4802	0.3710	0.5426	0.080*
C35	0.55920 (17)	0.2064 (5)	0.5170 (2)	0.0969 (12)
H35A	0.5786	0.1880	0.5585	0.116*
H35B	0.5591	0.1024	0.4954	0.116*
C36	0.6100 (2)	0.3198 (7)	0.4834 (3)	0.158 (2)
H36A	0.6587	0.2733	0.4819	0.236*
H36B	0.6118	0.4223	0.5050	0.236*
H36C	0.5922	0.3368	0.4418	0.236*
N1	0.49616 (14)	0.7082 (3)	0.58477 (12)	0.0676 (7)
N2	0.38608 (13)	0.7801 (3)	0.62497 (12)	0.0611 (6)
N3	0.4943 (2)	1.0041 (6)	0.8751 (2)	0.1309 (16)
N4	0.24691 (13)	0.2693 (3)	0.60257 (12)	0.0650 (7)
N5	0.35738 (13)	0.1906 (3)	0.56479 (12)	0.0613 (6)
N6	0.2498 (3)	−0.0585 (6)	0.3172 (2)	0.1410 (15)
F1	0.31626 (15)	0.5032 (4)	0.34690 (13)	0.1398 (11)
F2	0.42337 (15)	0.4596 (4)	0.84456 (14)	0.1372 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.089 (3)	0.117 (3)	0.067 (3)	−0.018 (2)	−0.006 (2)	−0.002 (2)
C2	0.067 (2)	0.096 (3)	0.074 (3)	−0.0098 (18)	−0.001 (2)	0.005 (2)
C3	0.0635 (19)	0.072 (2)	0.068 (2)	−0.0047 (15)	0.0065 (16)	0.0051 (17)
C4	0.0628 (18)	0.0559 (18)	0.0621 (19)	−0.0010 (14)	0.0053 (16)	0.0066 (15)
C5	0.071 (2)	0.095 (2)	0.068 (2)	−0.0126 (18)	0.0089 (18)	0.004 (2)
C6	0.093 (3)	0.133 (3)	0.062 (2)	−0.022 (2)	0.012 (2)	−0.002 (2)
C7	0.0590 (19)	0.0564 (18)	0.065 (2)	−0.0046 (15)	0.0097 (16)	0.0027 (15)
C8	0.0635 (19)	0.0615 (19)	0.067 (2)	−0.0058 (15)	0.0093 (17)	−0.0015 (17)
C9	0.058 (2)	0.073 (2)	0.065 (2)	−0.0064 (15)	0.0104 (15)	−0.0016 (16)
C10	0.060 (2)	0.113 (3)	0.077 (2)	−0.0174 (18)	0.0088 (18)	−0.014 (2)
C11	0.073 (2)	0.125 (3)	0.078 (2)	−0.021 (2)	0.005 (2)	−0.017 (2)
C12	0.070 (2)	0.099 (3)	0.074 (2)	−0.0165 (19)	0.0116 (19)	−0.0189 (19)
C13	0.071 (2)	0.076 (2)	0.074 (2)	−0.0082 (16)	0.0207 (18)	−0.0089 (18)
C14	0.099 (3)	0.122 (3)	0.085 (4)	−0.031 (3)	0.007 (3)	−0.026 (3)
C15	0.065 (2)	0.0583 (19)	0.078 (2)	0.0082 (15)	0.0058 (17)	0.0032 (16)
C16	0.0579 (18)	0.083 (2)	0.076 (2)	−0.0005 (16)	0.0135 (16)	−0.0017 (19)
C17	0.069 (2)	0.156 (4)	0.091 (3)	0.000 (2)	0.010 (2)	0.004 (3)
C18	0.092 (3)	0.198 (6)	0.183 (5)	−0.033 (3)	0.036 (4)	0.015 (5)
C19	0.097 (3)	0.113 (3)	0.063 (3)	0.014 (3)	−0.013 (2)	−0.012 (2)
C20	0.088 (3)	0.130 (3)	0.067 (3)	0.005 (2)	0.008 (2)	−0.005 (2)
C21	0.069 (2)	0.098 (3)	0.068 (2)	−0.0014 (17)	0.0107 (18)	0.0025 (19)
C22	0.0609 (18)	0.0591 (18)	0.065 (2)	0.0041 (15)	0.0058 (16)	0.0038 (16)
C23	0.071 (2)	0.076 (2)	0.069 (2)	−0.0035 (17)	0.0016 (17)	0.0030 (18)
C24	0.074 (2)	0.091 (3)	0.091 (3)	0.0001 (19)	−0.012 (2)	−0.006 (2)
C25	0.062 (2)	0.0577 (18)	0.061 (2)	−0.0029 (16)	0.0133 (17)	0.0030 (15)
C26	0.0589 (19)	0.069 (2)	0.065 (2)	−0.0079 (15)	0.0081 (15)	0.0049 (16)
C27	0.0607 (19)	0.090 (2)	0.072 (2)	−0.0086 (16)	0.0056 (17)	0.0017 (19)
C28	0.076 (2)	0.108 (3)	0.072 (2)	−0.016 (2)	−0.0049 (19)	0.003 (2)
C29	0.089 (2)	0.084 (2)	0.059 (2)	−0.005 (2)	0.0031 (19)	0.0002 (18)
C30	0.078 (2)	0.072 (2)	0.066 (2)	0.0032 (16)	0.0106 (18)	0.0026 (17)
C31	0.0617 (19)	0.0607 (18)	0.0626 (19)	−0.0015 (14)	0.0081 (16)	0.0075 (16)
C32	0.110 (3)	0.106 (3)	0.080 (4)	0.005 (3)	0.000 (3)	−0.007 (3)
C33	0.0559 (19)	0.0642 (19)	0.074 (2)	0.0112 (14)	0.0066 (15)	0.0062 (16)
C34	0.0583 (17)	0.0713 (19)	0.071 (2)	0.0043 (15)	0.0084 (16)	0.0067 (17)
C35	0.063 (2)	0.116 (3)	0.112 (3)	0.007 (2)	0.013 (2)	0.012 (3)
C36	0.087 (3)	0.156 (5)	0.230 (7)	−0.012 (3)	0.067 (4)	0.032 (4)
N1	0.0612 (16)	0.0771 (18)	0.0643 (17)	−0.0045 (13)	0.0086 (13)	−0.0026 (14)
N2	0.0543 (15)	0.0631 (14)	0.0657 (16)	0.0032 (12)	0.0110 (13)	0.0021 (13)
N3	0.132 (3)	0.164 (4)	0.097 (4)	−0.044 (3)	0.019 (2)	−0.049 (3)
N4	0.0541 (15)	0.0749 (16)	0.0660 (18)	−0.0038 (13)	0.0100 (12)	0.0026 (14)
N5	0.0544 (14)	0.0685 (16)	0.0610 (15)	0.0056 (12)	0.0079 (12)	0.0046 (13)
N6	0.180 (4)	0.165 (4)	0.078 (3)	0.032 (3)	−0.015 (3)	−0.036 (3)
F1	0.131 (2)	0.215 (3)	0.0735 (19)	−0.0524 (18)	−0.0074 (17)	−0.0214 (15)
F2	0.133 (2)	0.192 (3)	0.086 (2)	0.0002 (18)	−0.0240 (17)	−0.0340 (18)

Geometric parameters (Å, º)

C1—C6	1.353 (5)	C19—C20	1.346 (6)
C1—C2	1.357 (5)	C19—C24	1.359 (6)
C1—F1	1.367 (5)	C19—F2	1.365 (5)
C2—C3	1.380 (5)	C20—C21	1.376 (5)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.376 (4)	C21—C22	1.394 (4)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.388 (4)	C22—C23	1.380 (4)
C4—C7	1.475 (4)	C22—C25	1.466 (4)
C5—C6	1.368 (5)	C23—C24	1.392 (5)
C5—H5	0.9300	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C7—N1	1.315 (4)	C25—N4	1.316 (3)
C7—N2	1.382 (4)	C25—N5	1.376 (4)
C8—C13	1.377 (4)	C26—N4	1.381 (4)
C8—N2	1.389 (4)	C26—C27	1.393 (4)
C8—C9	1.398 (4)	C26—C31	1.400 (4)
C9—N1	1.385 (4)	C27—C28	1.376 (5)
C9—C10	1.387 (4)	C27—H27	0.9300
C10—C11	1.379 (5)	C28—C29	1.413 (5)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.383 (5)	C29—C30	1.375 (5)
C11—H11	0.9300	C29—C32	1.450 (6)
C12—C13	1.382 (5)	C30—C31	1.387 (4)
C12—C14	1.438 (6)	C30—H30	0.9300
C13—H13	0.9300	C31—N5	1.391 (4)
C14—N3	1.145 (5)	C32—N6	1.129 (5)
C15—N2	1.453 (4)	C33—N5	1.467 (3)
C15—C16	1.501 (4)	C33—C34	1.511 (4)
C15—H15A	0.9700	C33—H33A	0.9700
C15—H15B	0.9700	C33—H33B	0.9700
C16—C17	1.523 (5)	C34—C35	1.498 (4)
C16—H16A	0.9700	C34—H34A	0.9700
C16—H16B	0.9700	C34—H34B	0.9700
C17—C18	1.440 (5)	C35—C36	1.492 (6)
C17—H17A	0.9700	C35—H35A	0.9700
C17—H17B	0.9700	C35—H35B	0.9700
C18—H18A	0.9600	C36—H36A	0.9600
C18—H18B	0.9600	C36—H36B	0.9600
C18—H18C	0.9600	C36—H36C	0.9600
C6—C1—C2	123.7 (4)	C19—C20—H20	120.6
C6—C1—F1	118.8 (4)	C21—C20—H20	120.6
C2—C1—F1	117.5 (4)	C20—C21—C22	120.8 (3)
C1—C2—C3	117.7 (3)	C20—C21—H21	119.6
C1—C2—H2	121.2	C22—C21—H21	119.6
C3—C2—H2	121.2	C23—C22—C21	118.2 (3)
C4—C3—C2	120.9 (3)	C23—C22—C25	124.4 (3)
C4—C3—H3	119.6	C21—C22—C25	117.4 (3)
C2—C3—H3	119.6	C22—C23—C24	121.1 (3)
C3—C4—C5	118.8 (3)	C22—C23—H23	119.4
C3—C4—C7	123.6 (3)	C24—C23—H23	119.4
C5—C4—C7	117.4 (3)	C19—C24—C23	117.7 (3)
C6—C5—C4	120.7 (3)	C19—C24—H24	121.2
C6—C5—H5	119.6	C23—C24—H24	121.2
C4—C5—H5	119.6	N4—C25—N5	113.4 (3)
C1—C6—C5	118.2 (4)	N4—C25—C22	121.7 (3)
C1—C6—H6	120.9	N5—C25—C22	124.9 (3)
C5—C6—H6	120.9	N4—C26—C27	129.5 (3)
N1—C7—N2	112.9 (3)	N4—C26—C31	110.4 (3)
N1—C7—C4	122.0 (3)	C27—C26—C31	120.1 (3)
N2—C7—C4	125.1 (3)	C28—C27—C26	117.8 (3)
C13—C8—N2	131.8 (3)	C28—C27—H27	121.1
C13—C8—C9	122.9 (3)	C26—C27—H27	121.1
N2—C8—C9	105.4 (3)	C27—C28—C29	120.7 (3)
N1—C9—C10	129.6 (3)	C27—C28—H28	119.6
N1—C9—C8	110.4 (3)	C29—C28—H28	119.6
C10—C9—C8	120.0 (3)	C30—C29—C28	122.5 (3)
C11—C10—C9	117.7 (3)	C30—C29—C32	119.5 (4)
C11—C10—H10	121.2	C28—C29—C32	118.0 (4)
C9—C10—H10	121.2	C29—C30—C31	115.8 (3)
C10—C11—C12	121.1 (3)	C29—C30—H30	122.1
C10—C11—H11	119.5	C31—C30—H30	122.1
C12—C11—H11	119.5	C30—C31—N5	131.7 (3)
C13—C12—C11	122.6 (3)	C30—C31—C26	123.0 (3)
C13—C12—C14	118.9 (3)	N5—C31—C26	105.4 (3)
C11—C12—C14	118.5 (3)	N6—C32—C29	178.0 (6)
C8—C13—C12	115.7 (3)	N5—C33—C34	113.4 (2)
C8—C13—H13	122.1	N5—C33—H33A	108.9
C12—C13—H13	122.1	C34—C33—H33A	108.9
N3—C14—C12	178.6 (6)	N5—C33—H33B	108.9
N2—C15—C16	115.3 (2)	C34—C33—H33B	108.9
N2—C15—H15A	108.5	H33A—C33—H33B	107.7
C16—C15—H15A	108.5	C35—C34—C33	110.2 (3)
N2—C15—H15B	108.5	C35—C34—H34A	109.6
C16—C15—H15B	108.5	C33—C34—H34A	109.6
H15A—C15—H15B	107.5	C35—C34—H34B	109.6
C15—C16—C17	108.7 (3)	C33—C34—H34B	109.6
C15—C16—H16A	109.9	H34A—C34—H34B	108.1
C17—C16—H16A	109.9	C36—C35—C34	114.8 (4)
C15—C16—H16B	109.9	C36—C35—H35A	108.6
C17—C16—H16B	109.9	C34—C35—H35A	108.6
H16A—C16—H16B	108.3	C36—C35—H35B	108.6
C18—C17—C16	114.9 (4)	C34—C35—H35B	108.6
C18—C17—H17A	108.5	H35A—C35—H35B	107.6
C16—C17—H17A	108.5	C35—C36—H36A	109.5
C18—C17—H17B	108.5	C35—C36—H36B	109.5
C16—C17—H17B	108.5	H36A—C36—H36B	109.5
H17A—C17—H17B	107.5	C35—C36—H36C	109.5
C17—C18—H18A	109.5	H36A—C36—H36C	109.5
C17—C18—H18B	109.5	H36B—C36—H36C	109.5
H18A—C18—H18B	109.5	C7—N1—C9	105.2 (3)
C17—C18—H18C	109.5	C7—N2—C8	106.2 (2)
H18A—C18—H18C	109.5	C7—N2—C15	129.4 (3)
H18B—C18—H18C	109.5	C8—N2—C15	123.7 (3)
C20—C19—C24	123.5 (4)	C25—N4—C26	104.9 (3)
C20—C19—F2	119.1 (4)	C25—N5—C31	105.9 (2)
C24—C19—F2	117.4 (4)	C25—N5—C33	130.5 (3)
C19—C20—C21	118.7 (4)	C31—N5—C33	123.3 (3)