3-(4-Fluoro­phen­yl)-1,5-diphenyl-2-pyrazoline

The title compound, C₂₁H₁₇FN₂, crystallizes with two independent mol­ecules in the asymmetric unit. The pyrazoline and 4-fluoro­phenyl rings are planar. The phenyl ring at the 5-position and the pyrazoline heterocycle are almost perpendicular.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.156
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C40

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.17
           From the CIF: _reflns_number_total               7160
           From the CIF: _diffrn_reflns_limit_ max hkl   13.   13.   16.
           From the CIF: _diffrn_reflns_limit_ min hkl    0.  -13.  -16.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   14.   15.   17.
           Calculated minimum hkl  -14.  -15.  -17.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-Fluorophenyl)-1,5-diphenyl-2-pyrazoline

Crystal data

C21H17FN2	Z = 4
Mr = 316.37	F(000) = 664
Triclinic, P1	Dx = 1.252 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.491 (2) Å	Cell parameters from 25 reflections
b = 11.728 (2) Å	θ = 4–14°
c = 13.601 (3) Å	µ = 0.08 mm^−1
α = 89.44 (3)°	T = 293 K
β = 71.07 (3)°	Block, colourless
γ = 76.07 (3)°	0.23 × 0.22 × 0.19 mm
V = 1678.2 (6) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 27.2°, θmin = 1.6°
Graphite monochromator	h = 0→13
ω scans	k = −13→13
7526 measured reflections	l = −16→16
7160 independent reflections	3 standard reflections every 100 reflections
3538 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0765P)^2 + 0.0731P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
7160 reflections	Δρmax = 0.18 e Å^−3
434 parameters	Δρmin = −0.16 e Å^−3
0 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: 0.023 (2)

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

	x	y	z	Uiso*/Ueq
F1	0.08741 (14)	0.82353 (14)	0.43046 (13)	0.1086 (5)
N1	0.64631 (16)	0.30448 (15)	0.15456 (13)	0.0624 (5)
N2	0.53209 (15)	0.38750 (14)	0.17898 (13)	0.0570 (4)
C1	0.6245 (2)	0.24634 (18)	−0.00762 (16)	0.0632 (6)
H1A	0.5440	0.2975	0.0109	0.076*
C2	0.6727 (2)	0.1776 (2)	−0.10045 (19)	0.0837 (7)
H2B	0.6235	0.1828	−0.1436	0.100*
C3	0.7909 (3)	0.1021 (3)	−0.1304 (2)	0.0984 (9)
H3A	0.8219	0.0554	−0.1928	0.118*
C4	0.8628 (2)	0.0965 (2)	−0.0668 (2)	0.0896 (8)
H4A	0.9440	0.0464	−0.0871	0.108*
C5	0.8169 (2)	0.1641 (2)	0.02737 (18)	0.0708 (6)
H5A	0.8671	0.1589	0.0697	0.085*
C6	0.6958 (2)	0.23943 (17)	0.05826 (16)	0.0570 (5)
C7	0.7188 (2)	0.31911 (18)	0.22277 (16)	0.0609 (6)
H7A	0.7964	0.3415	0.1819	0.073*
C8	0.75378 (19)	0.20678 (17)	0.27632 (15)	0.0559 (5)
C9	0.8733 (2)	0.1669 (2)	0.28213 (19)	0.0803 (7)
H9A	0.9345	0.2083	0.2535	0.096*
C10	0.9035 (3)	0.0634 (3)	0.3315 (2)	0.1008 (10)
H10A	0.9851	0.0365	0.3347	0.121*
C11	0.8147 (3)	0.0016 (2)	0.3749 (2)	0.0949 (9)
H11A	0.8360	−0.0671	0.4067	0.114*
C12	0.6962 (3)	0.0412 (2)	0.37099 (19)	0.0842 (7)
H12A	0.6350	0.0005	0.4014	0.101*
C13	0.6651 (2)	0.14355 (19)	0.32141 (17)	0.0662 (6)
H13A	0.5831	0.1696	0.3187	0.079*
C14	0.6277 (2)	0.42368 (18)	0.29869 (18)	0.0679 (6)
H14A	0.6022	0.4009	0.3698	0.081*
H14B	0.6664	0.4891	0.2956	0.081*
C15	0.51749 (19)	0.45446 (16)	0.25977 (15)	0.0532 (5)
C16	0.40352 (19)	0.54965 (16)	0.30510 (15)	0.0532 (5)
C17	0.3937 (2)	0.62659 (19)	0.38623 (18)	0.0693 (6)
H17A	0.4607	0.6159	0.4123	0.083*
C18	0.2875 (2)	0.7183 (2)	0.42920 (19)	0.0771 (7)
H18A	0.2822	0.7691	0.4835	0.093*
C19	0.1923 (2)	0.7319 (2)	0.39032 (18)	0.0723 (6)
C20	0.1959 (2)	0.6575 (2)	0.3114 (2)	0.0867 (8)
H20A	0.1275	0.6684	0.2870	0.104*
C21	0.3025 (2)	0.5667 (2)	0.26910 (18)	0.0763 (7)
H21A	0.3062	0.5161	0.2153	0.092*
F2	0.09298 (14)	1.31327 (13)	0.31110 (14)	0.1144 (6)
N3	0.65692 (16)	0.78987 (15)	0.26011 (13)	0.0614 (5)
N4	0.54059 (15)	0.86991 (14)	0.30000 (13)	0.0549 (4)
C22	0.6427 (2)	0.73102 (17)	0.43473 (16)	0.0601 (5)
H22A	0.5622	0.7819	0.4617	0.072*
C23	0.6951 (2)	0.6627 (2)	0.50003 (19)	0.0757 (7)
H23A	0.6495	0.6684	0.5709	0.091*
C24	0.8135 (3)	0.5860 (2)	0.4622 (2)	0.0868 (8)
H24A	0.8477	0.5389	0.5065	0.104*
C25	0.8800 (2)	0.5805 (2)	0.3582 (2)	0.0821 (7)
H25A	0.9605	0.5295	0.3319	0.098*
C26	0.8300 (2)	0.64944 (18)	0.29096 (19)	0.0683 (6)
H26A	0.8775	0.6452	0.2206	0.082*
C27	0.70956 (19)	0.72450 (16)	0.32852 (16)	0.0541 (5)
C28	0.72907 (19)	0.81449 (17)	0.15408 (16)	0.0589 (5)
H28A	0.8048	0.8380	0.1556	0.071*
C29	0.76881 (18)	0.70874 (17)	0.07598 (15)	0.0529 (5)
C30	0.8857 (2)	0.6824 (2)	−0.00085 (17)	0.0684 (6)
H30A	0.9414	0.7295	−0.0045	0.082*
C31	0.9220 (2)	0.5872 (2)	−0.07292 (19)	0.0815 (7)
H31A	1.0017	0.5708	−0.1242	0.098*
C32	0.8416 (3)	0.5167 (2)	−0.06937 (18)	0.0748 (7)
H32A	0.8667	0.4525	−0.1177	0.090*
C33	0.7246 (2)	0.54148 (19)	0.00544 (18)	0.0723 (6)
H33A	0.6692	0.4945	0.0079	0.087*
C34	0.6878 (2)	0.63759 (18)	0.07863 (16)	0.0626 (6)
H34A	0.6080	0.6538	0.1296	0.075*
C35	0.6354 (2)	0.92108 (18)	0.13170 (17)	0.0677 (6)
H35A	0.6713	0.9888	0.1181	0.081*
H35B	0.6114	0.9026	0.0728	0.081*
C36	0.52495 (18)	0.94248 (16)	0.23027 (15)	0.0529 (5)
C37	0.40919 (19)	1.03749 (16)	0.25094 (16)	0.0527 (5)
C38	0.3991 (2)	1.12207 (19)	0.17893 (19)	0.0710 (6)
H38A	0.4657	1.1159	0.1165	0.085*
C39	0.2926 (2)	1.2142 (2)	0.1988 (2)	0.0827 (7)
H39A	0.2864	1.2699	0.1504	0.099*
C40	0.1977 (2)	1.2218 (2)	0.2898 (2)	0.0766 (7)
C41	0.2020 (2)	1.1395 (2)	0.3624 (2)	0.0842 (8)
H41A	0.1340	1.1459	0.4238	0.101*
C42	0.3087 (2)	1.0479 (2)	0.34238 (17)	0.0712 (6)
H42A	0.3132	0.9923	0.3911	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0860 (10)	0.0963 (11)	0.1091 (12)	0.0221 (9)	−0.0181 (9)	−0.0227 (9)
N1	0.0620 (11)	0.0566 (10)	0.0633 (11)	−0.0003 (9)	−0.0238 (9)	−0.0039 (9)
N2	0.0576 (11)	0.0520 (10)	0.0562 (10)	−0.0091 (8)	−0.0152 (8)	0.0015 (8)
C1	0.0645 (13)	0.0592 (13)	0.0611 (13)	−0.0146 (11)	−0.0149 (11)	−0.0013 (10)
C2	0.0785 (17)	0.0968 (19)	0.0693 (16)	−0.0193 (15)	−0.0174 (13)	−0.0172 (14)
C3	0.090 (2)	0.107 (2)	0.0771 (18)	−0.0072 (17)	−0.0116 (16)	−0.0343 (16)
C4	0.0686 (16)	0.0901 (19)	0.0846 (18)	−0.0003 (14)	−0.0051 (15)	−0.0170 (15)
C5	0.0658 (15)	0.0662 (14)	0.0698 (15)	−0.0091 (12)	−0.0139 (12)	−0.0021 (12)
C6	0.0632 (13)	0.0459 (11)	0.0561 (12)	−0.0149 (10)	−0.0113 (11)	0.0019 (9)
C7	0.0581 (13)	0.0567 (13)	0.0668 (13)	−0.0129 (10)	−0.0203 (11)	0.0021 (10)
C8	0.0537 (12)	0.0532 (12)	0.0559 (12)	−0.0037 (10)	−0.0181 (10)	−0.0067 (10)
C9	0.0562 (14)	0.0999 (19)	0.0755 (16)	−0.0018 (13)	−0.0221 (12)	0.0026 (14)
C10	0.082 (2)	0.117 (2)	0.0733 (18)	0.0367 (18)	−0.0293 (16)	−0.0077 (17)
C11	0.133 (3)	0.0651 (17)	0.0682 (17)	0.0183 (18)	−0.0400 (18)	−0.0067 (13)
C12	0.127 (2)	0.0622 (15)	0.0764 (17)	−0.0324 (16)	−0.0448 (16)	0.0080 (13)
C13	0.0732 (15)	0.0600 (13)	0.0720 (14)	−0.0171 (12)	−0.0325 (12)	0.0009 (11)
C14	0.0767 (15)	0.0497 (12)	0.0789 (15)	−0.0087 (11)	−0.0330 (13)	−0.0063 (11)
C15	0.0593 (13)	0.0465 (11)	0.0527 (12)	−0.0152 (10)	−0.0157 (10)	0.0035 (9)
C16	0.0578 (12)	0.0462 (11)	0.0528 (12)	−0.0144 (10)	−0.0137 (10)	0.0027 (9)
C17	0.0713 (15)	0.0589 (13)	0.0766 (15)	−0.0088 (12)	−0.0280 (12)	−0.0103 (12)
C18	0.0808 (17)	0.0621 (14)	0.0797 (16)	−0.0024 (13)	−0.0254 (14)	−0.0194 (12)
C19	0.0631 (15)	0.0640 (15)	0.0690 (15)	0.0020 (12)	−0.0070 (12)	−0.0056 (12)
C20	0.0687 (16)	0.0982 (19)	0.0845 (17)	0.0023 (15)	−0.0299 (14)	−0.0156 (15)
C21	0.0715 (16)	0.0773 (16)	0.0731 (15)	−0.0017 (13)	−0.0262 (13)	−0.0208 (12)
F2	0.0942 (11)	0.0851 (10)	0.1362 (14)	0.0306 (9)	−0.0395 (10)	0.0049 (9)
N3	0.0587 (10)	0.0543 (10)	0.0552 (10)	0.0061 (8)	−0.0123 (8)	0.0019 (8)
N4	0.0548 (10)	0.0481 (9)	0.0566 (10)	−0.0044 (8)	−0.0174 (8)	0.0021 (8)
C22	0.0616 (13)	0.0513 (12)	0.0654 (14)	−0.0104 (10)	−0.0212 (11)	0.0058 (10)
C23	0.0821 (17)	0.0755 (16)	0.0731 (15)	−0.0203 (14)	−0.0306 (13)	0.0239 (13)
C24	0.0872 (19)	0.0792 (17)	0.098 (2)	−0.0091 (15)	−0.0447 (17)	0.0315 (15)
C25	0.0682 (15)	0.0670 (15)	0.104 (2)	0.0027 (12)	−0.0344 (15)	0.0104 (14)
C26	0.0635 (14)	0.0565 (13)	0.0747 (15)	0.0005 (11)	−0.0202 (12)	0.0006 (11)
C27	0.0580 (12)	0.0397 (10)	0.0630 (13)	−0.0072 (9)	−0.0216 (10)	0.0033 (9)
C28	0.0570 (12)	0.0525 (12)	0.0590 (13)	−0.0080 (10)	−0.0123 (10)	0.0014 (10)
C29	0.0501 (12)	0.0493 (11)	0.0529 (11)	−0.0045 (9)	−0.0147 (9)	0.0068 (9)
C30	0.0562 (13)	0.0717 (15)	0.0668 (14)	−0.0117 (11)	−0.0094 (11)	−0.0053 (12)
C31	0.0655 (15)	0.0899 (18)	0.0701 (16)	0.0015 (14)	−0.0118 (12)	−0.0131 (14)
C32	0.0904 (18)	0.0582 (14)	0.0666 (15)	0.0071 (13)	−0.0321 (14)	−0.0061 (11)
C33	0.0955 (19)	0.0577 (14)	0.0742 (16)	−0.0244 (13)	−0.0386 (15)	0.0117 (12)
C34	0.0631 (13)	0.0621 (13)	0.0576 (13)	−0.0151 (11)	−0.0138 (10)	0.0075 (11)
C35	0.0742 (15)	0.0489 (12)	0.0660 (14)	−0.0045 (11)	−0.0128 (12)	0.0069 (10)
C36	0.0582 (12)	0.0436 (11)	0.0568 (12)	−0.0102 (9)	−0.0208 (10)	0.0031 (9)
C37	0.0571 (12)	0.0429 (11)	0.0596 (12)	−0.0095 (9)	−0.0237 (10)	0.0034 (9)
C38	0.0680 (14)	0.0595 (14)	0.0793 (15)	−0.0096 (12)	−0.0211 (12)	0.0216 (12)
C39	0.0844 (18)	0.0587 (15)	0.102 (2)	−0.0045 (13)	−0.0373 (16)	0.0249 (14)
C40	0.0695 (16)	0.0560 (14)	0.0954 (19)	0.0102 (12)	−0.0344 (15)	0.0022 (13)
C41	0.0666 (15)	0.0907 (18)	0.0720 (16)	0.0111 (14)	−0.0142 (12)	0.0032 (14)
C42	0.0674 (15)	0.0681 (15)	0.0643 (14)	0.0008 (12)	−0.0165 (12)	0.0136 (11)

Geometric parameters (Å, º)

F1—C19	1.366 (2)	F2—C40	1.357 (2)
N1—N2	1.374 (2)	N3—N4	1.378 (2)
N1—C6	1.396 (3)	N3—C27	1.396 (2)
N1—C7	1.469 (3)	N3—C28	1.477 (3)
N2—C15	1.298 (2)	N4—C36	1.295 (2)
C1—C2	1.379 (3)	C22—C23	1.376 (3)
C1—C6	1.386 (3)	C22—C27	1.392 (3)
C1—H1A	0.9300	C22—H22A	0.9300
C2—C3	1.365 (3)	C23—C24	1.375 (3)
C2—H2B	0.9300	C23—H23A	0.9300
C3—C4	1.368 (4)	C24—C25	1.366 (4)
C3—H3A	0.9300	C24—H24A	0.9300
C4—C5	1.389 (3)	C25—C26	1.386 (3)
C4—H4A	0.9300	C25—H25A	0.9300
C5—C6	1.389 (3)	C26—C27	1.384 (3)
C5—H5A	0.9300	C26—H26A	0.9300
C7—C8	1.531 (3)	C28—C29	1.521 (3)
C7—C14	1.540 (3)	C28—C35	1.540 (3)
C7—H7A	0.9800	C28—H28A	0.9800
C8—C9	1.368 (3)	C29—C30	1.374 (3)
C8—C13	1.384 (3)	C29—C34	1.384 (3)
C9—C10	1.407 (4)	C30—C31	1.384 (3)
C9—H9A	0.9300	C30—H30A	0.9300
C10—C11	1.367 (4)	C31—C32	1.370 (3)
C10—H10A	0.9300	C31—H31A	0.9300
C11—C12	1.347 (4)	C32—C33	1.363 (3)
C11—H11A	0.9300	C32—H32A	0.9300
C12—C13	1.399 (3)	C33—C34	1.400 (3)
C12—H12A	0.9300	C33—H33A	0.9300
C13—H13A	0.9300	C34—H34A	0.9300
C14—C15	1.491 (3)	C35—C36	1.490 (3)
C14—H14A	0.9700	C35—H35A	0.9700
C14—H14B	0.9700	C35—H35B	0.9700
C15—C16	1.459 (3)	C36—C37	1.463 (3)
C16—C21	1.372 (3)	C37—C42	1.378 (3)
C16—C17	1.391 (3)	C37—C38	1.399 (3)
C17—C18	1.381 (3)	C38—C39	1.375 (3)
C17—H17A	0.9300	C38—H38A	0.9300
C18—C19	1.338 (3)	C39—C40	1.345 (3)
C18—H18A	0.9300	C39—H39A	0.9300
C19—C20	1.373 (3)	C40—C41	1.378 (3)
C20—C21	1.376 (3)	C41—C42	1.373 (3)
C20—H20A	0.9300	C41—H41A	0.9300
C21—H21A	0.9300	C42—H42A	0.9300
N2—N1—C6	119.54 (17)	N4—N3—C27	119.02 (16)
N2—N1—C7	112.50 (16)	N4—N3—C28	112.10 (15)
C6—N1—C7	125.62 (17)	C27—N3—C28	125.33 (17)
C15—N2—N1	109.29 (17)	C36—N4—N3	109.16 (16)
C2—C1—C6	120.3 (2)	C23—C22—C27	120.4 (2)
C2—C1—H1A	119.9	C23—C22—H22A	119.8
C6—C1—H1A	119.9	C27—C22—H22A	119.8
C3—C2—C1	121.5 (3)	C24—C23—C22	121.1 (2)
C3—C2—H2B	119.3	C24—C23—H23A	119.4
C1—C2—H2B	119.3	C22—C23—H23A	119.4
C2—C3—C4	118.6 (2)	C25—C24—C23	118.6 (2)
C2—C3—H3A	120.7	C25—C24—H24A	120.7
C4—C3—H3A	120.7	C23—C24—H24A	120.7
C3—C4—C5	121.3 (2)	C24—C25—C26	121.4 (2)
C3—C4—H4A	119.3	C24—C25—H25A	119.3
C5—C4—H4A	119.3	C26—C25—H25A	119.3
C4—C5—C6	119.8 (2)	C27—C26—C25	120.0 (2)
C4—C5—H5A	120.1	C27—C26—H26A	120.0
C6—C5—H5A	120.1	C25—C26—H26A	120.0
C1—C6—C5	118.5 (2)	C26—C27—C22	118.44 (19)
C1—C6—N1	120.98 (19)	C26—C27—N3	120.03 (19)
C5—C6—N1	120.5 (2)	C22—C27—N3	121.52 (18)
N1—C7—C8	112.05 (17)	N3—C28—C29	112.28 (17)
N1—C7—C14	102.14 (16)	N3—C28—C35	102.32 (16)
C8—C7—C14	113.79 (17)	C29—C28—C35	113.75 (17)
N1—C7—H7A	109.5	N3—C28—H28A	109.4
C8—C7—H7A	109.5	C29—C28—H28A	109.4
C14—C7—H7A	109.5	C35—C28—H28A	109.4
C9—C8—C13	118.1 (2)	C30—C29—C34	118.0 (2)
C9—C8—C7	120.9 (2)	C30—C29—C28	120.8 (2)
C13—C8—C7	121.00 (19)	C34—C29—C28	121.25 (18)
C8—C9—C10	119.9 (3)	C29—C30—C31	121.2 (2)
C8—C9—H9A	120.0	C29—C30—H30A	119.4
C10—C9—H9A	120.0	C31—C30—H30A	119.4
C11—C10—C9	121.1 (3)	C32—C31—C30	120.5 (2)
C11—C10—H10A	119.5	C32—C31—H31A	119.7
C9—C10—H10A	119.5	C30—C31—H31A	119.7
C12—C11—C10	119.4 (3)	C33—C32—C31	119.5 (2)
C12—C11—H11A	120.3	C33—C32—H32A	120.2
C10—C11—H11A	120.3	C31—C32—H32A	120.2
C11—C12—C13	120.2 (3)	C32—C33—C34	120.0 (2)
C11—C12—H12A	119.9	C32—C33—H33A	120.0
C13—C12—H12A	119.9	C34—C33—H33A	120.0
C8—C13—C12	121.3 (2)	C29—C34—C33	120.8 (2)
C8—C13—H13A	119.4	C29—C34—H34A	119.6
C12—C13—H13A	119.4	C33—C34—H34A	119.6
C15—C14—C7	102.83 (17)	C36—C35—C28	102.52 (16)
C15—C14—H14A	111.2	C36—C35—H35A	111.3
C7—C14—H14A	111.2	C28—C35—H35A	111.3
C15—C14—H14B	111.2	C36—C35—H35B	111.3
C7—C14—H14B	111.2	C28—C35—H35B	111.3
H14A—C14—H14B	109.1	H35A—C35—H35B	109.2
N2—C15—C16	121.78 (18)	N4—C36—C37	121.32 (18)
N2—C15—C14	113.18 (18)	N4—C36—C35	113.83 (17)
C16—C15—C14	125.03 (18)	C37—C36—C35	124.82 (18)
C21—C16—C17	117.7 (2)	C42—C37—C38	118.23 (19)
C21—C16—C15	121.24 (19)	C42—C37—C36	121.21 (18)
C17—C16—C15	121.06 (19)	C38—C37—C36	120.54 (19)
C18—C17—C16	122.0 (2)	C39—C38—C37	121.2 (2)
C18—C17—H17A	119.0	C39—C38—H38A	119.4
C16—C17—H17A	119.0	C37—C38—H38A	119.4
C19—C18—C17	117.9 (2)	C40—C39—C38	118.5 (2)
C19—C18—H18A	121.0	C40—C39—H39A	120.8
C17—C18—H18A	121.0	C38—C39—H39A	120.8
C18—C19—F1	118.8 (2)	C39—C40—F2	119.1 (2)
C18—C19—C20	122.6 (2)	C39—C40—C41	122.5 (2)
F1—C19—C20	118.6 (2)	F2—C40—C41	118.4 (2)
C19—C20—C21	118.8 (2)	C42—C41—C40	118.8 (2)
C19—C20—H20A	120.6	C42—C41—H41A	120.6
C21—C20—H20A	120.6	C40—C41—H41A	120.6
C16—C21—C20	120.9 (2)	C41—C42—C37	120.7 (2)
C16—C21—H21A	119.5	C41—C42—H42A	119.6
C20—C21—H21A	119.5	C37—C42—H42A	119.6