1-[1-(4-Fluoro­phen­yl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]ethanone

The title compound, C₁₉H₁₆FNO, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. The dihedral angles between the pyrrole ring and fluoro­phenyl and unsubstituted phenyl rings are 44.9 (1) and 54.5 (2)°, respectively, in the first mol­ecule, and 72.8 (3) and 30.7 (3)° in the second mol­ecule. The crystal structure is stabilized by inter­molecular C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.120
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C19 H16 F N O

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

1-[1-(4-Fluorophenyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]ethanone

Crystal data

C19H16FNO	F(000) = 1232
Mr = 293.33	Dx = 1.279 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 725 reflections
a = 13.398 (6) Å	θ = 1.4–26.4°
b = 15.838 (7) Å	µ = 0.09 mm^−1
c = 14.680 (7) Å	T = 290 K
β = 101.979 (8)°	Block, colorless
V = 3047 (2) Å^3	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	6143 independent reflections
Radiation source: fine-focus sealed tube	4748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.974, Tmax = 0.991	k = −19→19
24441 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 0.4133P] where P = (Fo^2 + 2Fc^2)/3
6143 reflections	(Δ/σ)max < 0.001
525 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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
N1	1.28046 (9)	0.30873 (8)	0.73561 (8)	0.0453 (3)
N2	0.76449 (8)	0.18955 (7)	0.67252 (8)	0.0415 (3)
F1	1.19950 (11)	0.00793 (7)	0.89347 (10)	0.1003 (4)
F2	0.87086 (10)	0.46957 (8)	0.89391 (9)	0.0986 (4)
O2	1.51397 (11)	0.49460 (9)	0.80346 (12)	0.0920 (5)
O4	0.86055 (10)	−0.06091 (8)	0.62891 (10)	0.0788 (4)
C1	1.43236 (14)	0.50088 (11)	0.74864 (13)	0.0624 (4)
C2	1.35656 (12)	0.43310 (10)	0.73145 (11)	0.0506 (4)
C3	1.25999 (12)	0.43468 (10)	0.66920 (11)	0.0511 (4)
C4	1.21361 (11)	0.35875 (9)	0.67204 (10)	0.0456 (3)
C5	1.11642 (11)	0.32933 (9)	0.61553 (10)	0.0467 (3)
C6	1.03960 (12)	0.38775 (11)	0.58415 (11)	0.0546 (4)
C7	0.95019 (14)	0.36411 (14)	0.52512 (12)	0.0666 (5)
C8	0.93470 (16)	0.28194 (14)	0.49659 (14)	0.0756 (6)
C9	1.00936 (16)	0.22302 (14)	0.52716 (13)	0.0738 (5)
C10	1.09926 (14)	0.24611 (11)	0.58577 (11)	0.0583 (4)
C11	1.18765 (11)	0.22794 (10)	0.83156 (10)	0.0487 (3)
C12	1.16769 (14)	0.15250 (11)	0.87118 (12)	0.0584 (4)
C13	1.21746 (14)	0.08147 (10)	0.85231 (12)	0.0629 (4)
C14	1.28572 (15)	0.08102 (11)	0.79516 (13)	0.0636 (4)
C15	1.30528 (13)	0.15644 (10)	0.75552 (12)	0.0551 (4)
C16	1.25682 (11)	0.22961 (9)	0.77384 (10)	0.0444 (3)
C17	1.36723 (11)	0.35377 (10)	0.77143 (10)	0.0481 (3)
C18	1.45378 (15)	0.31628 (15)	0.83886 (15)	0.0664 (5)
C19	0.41927 (14)	0.29292 (12)	0.55803 (12)	0.0588 (4)
C20	0.44588 (15)	0.37453 (12)	0.54315 (12)	0.0633 (5)
C21	0.54693 (16)	0.39521 (12)	0.55198 (13)	0.0686 (5)
C22	0.62185 (14)	0.33427 (10)	0.57365 (12)	0.0590 (4)
C23	0.67174 (10)	0.18310 (9)	0.60870 (9)	0.0418 (3)
C24	0.79423 (10)	0.26066 (9)	0.73247 (10)	0.0427 (3)
C25	0.88641 (12)	0.30064 (10)	0.73441 (11)	0.0516 (4)
C26	0.91254 (14)	0.37091 (11)	0.78984 (13)	0.0614 (4)
C27	0.84562 (14)	0.40006 (10)	0.84038 (12)	0.0618 (4)
C28	0.75418 (14)	0.36196 (12)	0.84013 (13)	0.0631 (4)
C29	0.72908 (12)	0.29094 (10)	0.78587 (11)	0.0518 (4)
C30	0.66763 (11)	0.10499 (9)	0.57041 (10)	0.0457 (3)
C31	0.75828 (11)	0.06109 (9)	0.61032 (10)	0.0449 (3)
C32	0.81696 (10)	0.11489 (9)	0.67389 (10)	0.0445 (3)
C33	0.91680 (12)	0.09982 (11)	0.73823 (13)	0.0622 (4)
C34	0.78353 (12)	−0.02544 (10)	0.58886 (11)	0.0530 (4)
C35	0.59606 (11)	0.25134 (9)	0.58848 (9)	0.0440 (3)
C36	0.49359 (11)	0.23166 (10)	0.58115 (10)	0.0492 (4)
C37	1.40543 (17)	0.58097 (12)	0.69558 (15)	0.0789 (6)
C38	0.70983 (15)	−0.07119 (11)	0.51481 (14)	0.0693 (5)
H3	1.2317 (12)	0.4798 (11)	0.6272 (12)	0.058 (5)*
H6	1.0502 (13)	0.4445 (12)	0.6046 (12)	0.065 (5)*
H7	0.8991 (15)	0.4051 (12)	0.5057 (14)	0.074 (6)*
H8	0.8740 (17)	0.2639 (13)	0.4604 (15)	0.090 (7)*
H9	0.9993 (16)	0.1670 (13)	0.5117 (15)	0.081 (6)*
H10	1.1528 (14)	0.2042 (11)	0.6072 (12)	0.065 (5)*
H11	1.1547 (12)	0.2798 (11)	0.8425 (11)	0.052 (4)*
H12	1.1241 (15)	0.1514 (12)	0.9118 (14)	0.075 (6)*
H14	1.3204 (14)	0.0298 (12)	0.7861 (13)	0.072 (5)*
H15	1.3515 (14)	0.1574 (11)	0.7157 (13)	0.063 (5)*
H18B	1.500 (3)	0.293 (2)	0.811 (2)	0.150 (12)*
H18A	1.4903 (19)	0.3596 (16)	0.8759 (19)	0.109 (8)*
H18C	1.434 (2)	0.2752 (19)	0.879 (2)	0.130 (10)*
H19	0.3468 (15)	0.2780 (11)	0.5510 (12)	0.068 (5)*
H20	0.3912 (13)	0.4164 (11)	0.5269 (11)	0.058 (4)*
H21	0.5670 (15)	0.4515 (13)	0.5413 (14)	0.079 (6)*
H22	0.6901 (15)	0.3486 (11)	0.5774 (13)	0.067 (5)*
H25	0.9316 (13)	0.2794 (11)	0.6967 (12)	0.060 (5)*
H26	0.9742 (16)	0.3986 (12)	0.7926 (14)	0.077 (6)*
H28	0.7091 (15)	0.3842 (12)	0.8743 (14)	0.078 (6)*
H29	0.6654 (14)	0.2622 (11)	0.7844 (12)	0.060 (5)*
H30	0.6122 (12)	0.0842 (9)	0.5231 (11)	0.049 (4)*
H33A	0.9711	0.1146	0.7077	0.093*
H33B	0.9224	0.0413	0.7555	0.093*
H33C	0.9212	0.1338	0.7931	0.093*
H36	0.4747 (12)	0.1753 (11)	0.5935 (11)	0.055 (4)*
H37A	1.4570	0.6226	0.7171	0.118*
H37B	1.3408	0.6011	0.7051	0.118*
H37C	1.4012	0.5707	0.6304	0.118*
H38A	0.7326	−0.1282	0.5105	0.104*
H38B	0.7060	−0.0432	0.4561	0.104*
H38C	0.6436	−0.0715	0.5303	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0427 (6)	0.0492 (7)	0.0442 (6)	−0.0012 (5)	0.0095 (5)	−0.0001 (5)
N2	0.0369 (6)	0.0406 (6)	0.0450 (6)	0.0009 (5)	0.0039 (5)	0.0007 (5)
F1	0.1262 (11)	0.0598 (7)	0.1184 (10)	−0.0166 (7)	0.0336 (8)	0.0226 (6)
F2	0.1027 (9)	0.0770 (8)	0.1093 (9)	−0.0133 (7)	0.0067 (7)	−0.0438 (7)
O2	0.0616 (8)	0.0902 (10)	0.1176 (12)	−0.0258 (7)	0.0031 (8)	−0.0064 (9)
O4	0.0659 (8)	0.0554 (7)	0.1073 (10)	0.0211 (6)	−0.0001 (7)	−0.0034 (7)
C1	0.0602 (10)	0.0610 (10)	0.0716 (11)	−0.0120 (8)	0.0265 (9)	−0.0135 (8)
C2	0.0485 (8)	0.0524 (9)	0.0542 (8)	−0.0058 (7)	0.0182 (7)	−0.0064 (7)
C3	0.0550 (9)	0.0479 (8)	0.0524 (9)	0.0001 (7)	0.0160 (7)	0.0011 (7)
C4	0.0459 (8)	0.0482 (8)	0.0433 (7)	0.0017 (6)	0.0109 (6)	−0.0017 (6)
C5	0.0483 (8)	0.0532 (8)	0.0392 (7)	0.0000 (6)	0.0102 (6)	−0.0014 (6)
C6	0.0544 (9)	0.0582 (10)	0.0501 (9)	0.0040 (7)	0.0083 (7)	−0.0010 (7)
C7	0.0582 (10)	0.0815 (13)	0.0555 (10)	0.0137 (9)	0.0012 (8)	0.0001 (9)
C8	0.0660 (12)	0.0915 (15)	0.0590 (11)	−0.0058 (10)	−0.0107 (9)	−0.0099 (10)
C9	0.0844 (13)	0.0650 (12)	0.0625 (11)	−0.0060 (10)	−0.0067 (10)	−0.0141 (9)
C10	0.0637 (10)	0.0561 (9)	0.0504 (9)	0.0035 (8)	0.0012 (8)	−0.0063 (7)
C11	0.0453 (8)	0.0513 (9)	0.0495 (8)	−0.0029 (7)	0.0094 (7)	−0.0046 (7)
C12	0.0561 (10)	0.0655 (11)	0.0550 (9)	−0.0143 (8)	0.0144 (8)	0.0008 (8)
C13	0.0704 (11)	0.0482 (9)	0.0662 (10)	−0.0115 (8)	0.0056 (9)	0.0057 (8)
C14	0.0686 (11)	0.0480 (9)	0.0718 (11)	0.0068 (8)	0.0095 (9)	−0.0013 (8)
C15	0.0529 (9)	0.0579 (10)	0.0557 (9)	0.0052 (7)	0.0142 (8)	−0.0018 (7)
C16	0.0423 (7)	0.0469 (8)	0.0426 (7)	−0.0022 (6)	0.0058 (6)	−0.0014 (6)
C17	0.0419 (8)	0.0578 (9)	0.0459 (8)	−0.0051 (6)	0.0122 (6)	−0.0074 (7)
C18	0.0497 (10)	0.0790 (13)	0.0657 (11)	−0.0039 (9)	0.0010 (9)	0.0019 (10)
C19	0.0479 (9)	0.0719 (11)	0.0541 (9)	0.0144 (8)	0.0053 (7)	−0.0058 (8)
C20	0.0678 (11)	0.0650 (11)	0.0539 (9)	0.0282 (9)	0.0055 (8)	0.0033 (8)
C21	0.0797 (13)	0.0484 (10)	0.0724 (12)	0.0124 (9)	0.0035 (9)	0.0138 (8)
C22	0.0541 (10)	0.0517 (9)	0.0674 (11)	0.0020 (7)	0.0038 (8)	0.0126 (8)
C23	0.0366 (7)	0.0436 (7)	0.0430 (7)	0.0015 (6)	0.0029 (6)	0.0025 (6)
C24	0.0399 (7)	0.0421 (7)	0.0434 (7)	0.0005 (6)	0.0026 (6)	0.0028 (6)
C25	0.0447 (8)	0.0543 (9)	0.0555 (9)	−0.0048 (7)	0.0098 (7)	−0.0002 (7)
C26	0.0514 (9)	0.0579 (10)	0.0709 (11)	−0.0132 (8)	0.0038 (8)	−0.0027 (8)
C27	0.0652 (11)	0.0497 (9)	0.0636 (10)	−0.0029 (8)	−0.0028 (8)	−0.0127 (7)
C28	0.0607 (10)	0.0651 (11)	0.0635 (10)	0.0061 (8)	0.0128 (8)	−0.0140 (8)
C29	0.0435 (8)	0.0547 (9)	0.0568 (9)	−0.0008 (7)	0.0094 (7)	−0.0040 (7)
C30	0.0420 (8)	0.0458 (8)	0.0461 (8)	0.0005 (6)	0.0019 (6)	−0.0003 (6)
C31	0.0430 (8)	0.0424 (7)	0.0489 (8)	0.0031 (6)	0.0085 (6)	0.0037 (6)
C32	0.0394 (7)	0.0448 (8)	0.0488 (8)	0.0044 (6)	0.0075 (6)	0.0052 (6)
C33	0.0473 (9)	0.0598 (10)	0.0715 (11)	0.0093 (7)	−0.0056 (8)	0.0017 (8)
C34	0.0522 (9)	0.0446 (8)	0.0627 (9)	0.0057 (7)	0.0134 (7)	0.0029 (7)
C35	0.0444 (8)	0.0453 (8)	0.0392 (7)	0.0065 (6)	0.0014 (6)	−0.0002 (6)
C36	0.0455 (8)	0.0515 (9)	0.0483 (8)	0.0039 (7)	0.0042 (6)	−0.0039 (7)
C37	0.0896 (14)	0.0597 (11)	0.0930 (14)	−0.0206 (10)	0.0320 (12)	−0.0083 (10)
C38	0.0811 (12)	0.0476 (9)	0.0754 (12)	0.0003 (8)	0.0077 (10)	−0.0092 (8)

Geometric parameters (Å, º)

N1—C17	1.3723 (19)	C10—H10	0.980 (19)
N1—C4	1.3978 (19)	C22—C21	1.381 (2)
N1—C16	1.4350 (19)	C22—H22	0.933 (19)
N2—C32	1.3737 (18)	C19—C20	1.370 (3)
N2—C23	1.3961 (18)	C19—H19	0.984 (19)
N2—C24	1.4340 (19)	C34—C38	1.495 (2)
F2—C27	1.3541 (19)	C25—C26	1.380 (2)
F1—C13	1.357 (2)	C25—H25	0.962 (18)
O4—C34	1.2143 (19)	C12—H12	0.92 (2)
C23—C30	1.355 (2)	C32—C33	1.488 (2)
C23—C35	1.4694 (19)	C20—C21	1.373 (3)
C16—C11	1.380 (2)	C20—H20	0.980 (17)
C16—C15	1.382 (2)	C15—C14	1.377 (2)
C36—C19	1.381 (2)	C15—H15	0.937 (19)
C36—C35	1.390 (2)	C1—C37	1.493 (3)
C36—H36	0.956 (17)	C26—C27	1.358 (3)
C35—C22	1.387 (2)	C26—H26	0.93 (2)
C31—C32	1.382 (2)	C27—C28	1.365 (3)
C31—C30	1.417 (2)	C33—H33A	0.9600
C31—C34	1.462 (2)	C33—H33B	0.9600
C17—C2	1.382 (2)	C33—H33C	0.9600
C17—C18	1.483 (2)	C9—C8	1.373 (3)
C5—C6	1.390 (2)	C9—H9	0.92 (2)
C5—C10	1.393 (2)	C18—H18B	0.90 (4)
C5—C4	1.467 (2)	C18—H18A	0.95 (3)
C30—H30	0.963 (16)	C18—H18C	0.95 (3)
C4—C3	1.358 (2)	C14—H14	0.958 (19)
C2—C3	1.421 (2)	C6—C7	1.377 (2)
C2—C1	1.463 (2)	C6—H6	0.948 (19)
C11—C12	1.379 (2)	C21—H21	0.95 (2)
C11—H11	0.962 (17)	C28—H28	0.93 (2)
C13—C14	1.363 (3)	C7—C8	1.370 (3)
C13—C12	1.365 (3)	C7—H7	0.94 (2)
O2—C1	1.220 (2)	C37—H37A	0.9600
C3—H3	0.968 (17)	C37—H37B	0.9600
C24—C29	1.375 (2)	C37—H37C	0.9600
C24—C25	1.383 (2)	C38—H38A	0.9600
C29—C28	1.379 (2)	C38—H38B	0.9600
C29—H29	0.963 (18)	C38—H38C	0.9600
C10—C9	1.376 (3)	C8—H8	0.92 (2)
C17—N1—C4	109.61 (13)	C13—C12—C11	118.87 (17)
C17—N1—C16	122.84 (12)	C13—C12—H12	121.4 (12)
C4—N1—C16	126.39 (12)	C11—C12—H12	119.7 (12)
C32—N2—C23	109.17 (11)	N2—C32—C31	107.64 (12)
C32—N2—C24	126.22 (12)	N2—C32—C33	122.50 (13)
C23—N2—C24	124.37 (11)	C31—C32—C33	129.81 (13)
C30—C23—N2	107.40 (12)	C19—C20—C21	119.62 (16)
C30—C23—C35	128.36 (13)	C19—C20—H20	118.1 (10)
N2—C23—C35	124.23 (12)	C21—C20—H20	122.3 (10)
C11—C16—C15	120.41 (15)	C14—C15—C16	120.45 (16)
C11—C16—N1	119.20 (13)	C14—C15—H15	119.1 (11)
C15—C16—N1	120.36 (14)	C16—C15—H15	120.4 (11)
C19—C36—C35	120.77 (16)	O2—C1—C2	123.30 (17)
C19—C36—H36	119.8 (10)	O2—C1—C37	120.00 (16)
C35—C36—H36	119.4 (10)	C2—C1—C37	116.70 (17)
C22—C35—C36	118.32 (14)	C27—C26—C25	118.74 (16)
C22—C35—C23	122.98 (14)	C27—C26—H26	119.9 (12)
C36—C35—C23	118.67 (13)	C25—C26—H26	121.4 (12)
C32—C31—C30	107.18 (13)	F2—C27—C26	118.68 (16)
C32—C31—C34	126.79 (13)	F2—C27—C28	118.48 (17)
C30—C31—C34	126.02 (14)	C26—C27—C28	122.84 (16)
N1—C17—C2	107.77 (13)	C32—C33—H33A	109.5
N1—C17—C18	122.03 (15)	C32—C33—H33B	109.5
C2—C17—C18	130.17 (15)	H33A—C33—H33B	109.5
C6—C5—C10	117.62 (15)	C32—C33—H33C	109.5
C6—C5—C4	119.04 (14)	H33A—C33—H33C	109.5
C10—C5—C4	123.18 (14)	H33B—C33—H33C	109.5
C23—C30—C31	108.60 (13)	C8—C9—C10	120.47 (19)
C23—C30—H30	124.7 (9)	C8—C9—H9	121.1 (13)
C31—C30—H30	126.7 (9)	C10—C9—H9	118.4 (13)
C3—C4—N1	106.77 (13)	C17—C18—H18B	112 (2)
C3—C4—C5	128.45 (14)	C17—C18—H18A	109.4 (15)
N1—C4—C5	124.61 (13)	H18B—C18—H18A	104 (2)
C17—C2—C3	106.82 (13)	C17—C18—H18C	113.8 (17)
C17—C2—C1	125.95 (15)	H18B—C18—H18C	109 (3)
C3—C2—C1	127.21 (15)	H18A—C18—H18C	109 (2)
C12—C11—C16	119.30 (16)	C13—C14—C15	117.79 (16)
C12—C11—H11	122.3 (10)	C13—C14—H14	119.8 (11)
C16—C11—H11	118.4 (10)	C15—C14—H14	122.4 (11)
F1—C13—C14	118.25 (17)	C7—C6—C5	121.03 (17)
F1—C13—C12	118.55 (17)	C7—C6—H6	120.7 (11)
C14—C13—C12	123.19 (16)	C5—C6—H6	118.3 (11)
C4—C3—C2	109.03 (14)	C20—C21—C22	120.69 (18)
C4—C3—H3	123.5 (10)	C20—C21—H21	121.0 (12)
C2—C3—H3	127.4 (10)	C22—C21—H21	118.3 (12)
C29—C24—C25	119.90 (14)	C27—C28—C29	118.25 (17)
C29—C24—N2	119.70 (13)	C27—C28—H28	120.9 (12)
C25—C24—N2	120.36 (13)	C29—C28—H28	120.8 (12)
C24—C29—C28	120.41 (16)	C8—C7—C6	120.51 (18)
C24—C29—H29	119.1 (10)	C8—C7—H7	120.5 (12)
C28—C29—H29	120.4 (10)	C6—C7—H7	119.0 (12)
C9—C10—C5	120.91 (17)	C1—C37—H37A	109.5
C9—C10—H10	120.5 (11)	C1—C37—H37B	109.5
C5—C10—H10	118.6 (11)	H37A—C37—H37B	109.5
C21—C22—C35	120.34 (18)	C1—C37—H37C	109.5
C21—C22—H22	120.0 (11)	H37A—C37—H37C	109.5
C35—C22—H22	119.6 (11)	H37B—C37—H37C	109.5
C20—C19—C36	120.24 (17)	C34—C38—H38A	109.5
C20—C19—H19	119.6 (11)	C34—C38—H38B	109.5
C36—C19—H19	120.2 (11)	H38A—C38—H38B	109.5
O4—C34—C31	122.74 (15)	C34—C38—H38C	109.5
O4—C34—C38	119.63 (15)	H38A—C38—H38C	109.5
C31—C34—C38	117.62 (14)	H38B—C38—H38C	109.5
C26—C25—C24	119.83 (16)	C7—C8—C9	119.46 (18)
C26—C25—H25	120.6 (10)	C7—C8—H8	122.1 (14)
C24—C25—H25	119.6 (10)	C9—C8—H8	118.4 (14)
C32—N2—C23—C30	−0.51 (16)	C6—C5—C10—C9	0.2 (3)
C24—N2—C23—C30	−175.26 (13)	C4—C5—C10—C9	−175.14 (17)
C32—N2—C23—C35	−179.57 (13)	C36—C35—C22—C21	−0.1 (2)
C24—N2—C23—C35	5.7 (2)	C23—C35—C22—C21	177.94 (16)
C17—N1—C16—C11	100.50 (17)	C35—C36—C19—C20	−0.9 (2)
C4—N1—C16—C11	−65.85 (19)	C32—C31—C34—O4	2.6 (3)
C17—N1—C16—C15	−77.38 (19)	C30—C31—C34—O4	−176.33 (16)
C4—N1—C16—C15	116.27 (17)	C32—C31—C34—C38	−177.95 (15)
C19—C36—C35—C22	1.1 (2)	C30—C31—C34—C38	3.1 (2)
C19—C36—C35—C23	−177.01 (14)	C29—C24—C25—C26	−0.1 (2)
C30—C23—C35—C22	−133.36 (18)	N2—C24—C25—C26	177.63 (14)
N2—C23—C35—C22	45.5 (2)	F1—C13—C12—C11	178.27 (15)
C30—C23—C35—C36	44.7 (2)	C14—C13—C12—C11	−0.7 (3)
N2—C23—C35—C36	−136.44 (15)	C16—C11—C12—C13	0.2 (2)
C4—N1—C17—C2	0.25 (16)	C23—N2—C32—C31	0.60 (15)
C16—N1—C17—C2	−168.12 (13)	C24—N2—C32—C31	175.24 (13)
C4—N1—C17—C18	−178.13 (16)	C23—N2—C32—C33	−176.99 (14)
C16—N1—C17—C18	13.5 (2)	C24—N2—C32—C33	−2.4 (2)
N2—C23—C30—C31	0.21 (16)	C30—C31—C32—N2	−0.46 (16)
C35—C23—C30—C31	179.22 (14)	C34—C31—C32—N2	−179.56 (14)
C32—C31—C30—C23	0.15 (17)	C30—C31—C32—C33	176.89 (15)
C34—C31—C30—C23	179.26 (14)	C34—C31—C32—C33	−2.2 (3)
C17—N1—C4—C3	−0.02 (16)	C36—C19—C20—C21	−0.5 (3)
C16—N1—C4—C3	167.83 (13)	C11—C16—C15—C14	−0.5 (2)
C17—N1—C4—C5	175.62 (13)	N1—C16—C15—C14	177.39 (15)
C16—N1—C4—C5	−16.5 (2)	C17—C2—C1—O2	−2.0 (3)
C6—C5—C4—C3	−30.6 (2)	C3—C2—C1—O2	−179.97 (17)
C10—C5—C4—C3	144.69 (17)	C17—C2—C1—C37	178.43 (16)
C6—C5—C4—N1	154.77 (14)	C3—C2—C1—C37	0.5 (2)
C10—C5—C4—N1	−30.0 (2)	C24—C25—C26—C27	−1.1 (3)
N1—C17—C2—C3	−0.37 (16)	C25—C26—C27—F2	−179.26 (16)
C18—C17—C2—C3	177.84 (18)	C25—C26—C27—C28	1.2 (3)
N1—C17—C2—C1	−178.68 (14)	C5—C10—C9—C8	0.2 (3)
C18—C17—C2—C1	−0.5 (3)	F1—C13—C14—C15	−178.44 (16)
C15—C16—C11—C12	0.3 (2)	C12—C13—C14—C15	0.5 (3)
N1—C16—C11—C12	−177.58 (13)	C16—C15—C14—C13	0.1 (3)
N1—C4—C3—C2	−0.21 (16)	C10—C5—C6—C7	−0.5 (2)
C5—C4—C3—C2	−175.62 (14)	C4—C5—C6—C7	174.97 (15)
C17—C2—C3—C4	0.36 (17)	C19—C20—C21—C22	1.5 (3)
C1—C2—C3—C4	178.65 (15)	C35—C22—C21—C20	−1.2 (3)
C32—N2—C24—C29	−123.10 (16)	F2—C27—C28—C29	−179.67 (16)
C23—N2—C24—C29	50.8 (2)	C26—C27—C28—C29	−0.2 (3)
C32—N2—C24—C25	59.1 (2)	C24—C29—C28—C27	−1.1 (3)
C23—N2—C24—C25	−127.00 (15)	C5—C6—C7—C8	0.6 (3)
C25—C24—C29—C28	1.2 (2)	C6—C7—C8—C9	−0.2 (3)
N2—C24—C29—C28	−176.55 (14)	C10—C9—C8—C7	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2	0.95 (3)	2.44 (3)	3.012 (3)	119 (2)
C33—H33B···O4	0.96	2.47	3.020 (2)	116
C11—H11···O4^i	0.96 (2)	2.57 (2)	3.477 (3)	157 (1)
C25—H25···Cg2^ii	0.96 (2)	2.66 (2)	3.514 (2)	148 (1)
C12—H12···Cg2^iii	0.92 (2)	2.80 (2)	3.687 (3)	162 (2)
C26—H26···O4^i	0.93 (2)	2.36 (2)	3.213 (3)	152 (2)

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2.