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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016576/sj2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016576/sj2058Isup2.hkl
Contains datablock I

CCDC reference: 610897

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

Computing details top

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 top
Crystal data top
C19H16FNOF(000) = 1232
Mr = 293.33Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 725 reflections
a = 13.398 (6) Åθ = 1.4–26.4°
b = 15.838 (7) ŵ = 0.09 mm1
c = 14.680 (7) ÅT = 290 K
β = 101.979 (8)°Block, colorless
V = 3047 (2) Å30.30 × 0.25 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
6143 independent reflections
Radiation source: fine-focus sealed tube4748 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1615
Tmin = 0.974, Tmax = 0.991k = 1919
24441 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0691P)2 + 0.4133P]
where P = (Fo2 + 2Fc2)/3
6143 reflections(Δ/σ)max < 0.001
525 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N11.28046 (9)0.30873 (8)0.73561 (8)0.0453 (3)
N20.76449 (8)0.18955 (7)0.67252 (8)0.0415 (3)
F11.19950 (11)0.00793 (7)0.89347 (10)0.1003 (4)
F20.87086 (10)0.46957 (8)0.89391 (9)0.0986 (4)
O21.51397 (11)0.49460 (9)0.80346 (12)0.0920 (5)
O40.86055 (10)0.06091 (8)0.62891 (10)0.0788 (4)
C11.43236 (14)0.50088 (11)0.74864 (13)0.0624 (4)
C21.35656 (12)0.43310 (10)0.73145 (11)0.0506 (4)
C31.25999 (12)0.43468 (10)0.66920 (11)0.0511 (4)
C41.21361 (11)0.35875 (9)0.67204 (10)0.0456 (3)
C51.11642 (11)0.32933 (9)0.61553 (10)0.0467 (3)
C61.03960 (12)0.38775 (11)0.58415 (11)0.0546 (4)
C70.95019 (14)0.36411 (14)0.52512 (12)0.0666 (5)
C80.93470 (16)0.28194 (14)0.49659 (14)0.0756 (6)
C91.00936 (16)0.22302 (14)0.52716 (13)0.0738 (5)
C101.09926 (14)0.24611 (11)0.58577 (11)0.0583 (4)
C111.18765 (11)0.22794 (10)0.83156 (10)0.0487 (3)
C121.16769 (14)0.15250 (11)0.87118 (12)0.0584 (4)
C131.21746 (14)0.08147 (10)0.85231 (12)0.0629 (4)
C141.28572 (15)0.08102 (11)0.79516 (13)0.0636 (4)
C151.30528 (13)0.15644 (10)0.75552 (12)0.0551 (4)
C161.25682 (11)0.22961 (9)0.77384 (10)0.0444 (3)
C171.36723 (11)0.35377 (10)0.77143 (10)0.0481 (3)
C181.45378 (15)0.31628 (15)0.83886 (15)0.0664 (5)
C190.41927 (14)0.29292 (12)0.55803 (12)0.0588 (4)
C200.44588 (15)0.37453 (12)0.54315 (12)0.0633 (5)
C210.54693 (16)0.39521 (12)0.55198 (13)0.0686 (5)
C220.62185 (14)0.33427 (10)0.57365 (12)0.0590 (4)
C230.67174 (10)0.18310 (9)0.60870 (9)0.0418 (3)
C240.79423 (10)0.26066 (9)0.73247 (10)0.0427 (3)
C250.88641 (12)0.30064 (10)0.73441 (11)0.0516 (4)
C260.91254 (14)0.37091 (11)0.78984 (13)0.0614 (4)
C270.84562 (14)0.40006 (10)0.84038 (12)0.0618 (4)
C280.75418 (14)0.36196 (12)0.84013 (13)0.0631 (4)
C290.72908 (12)0.29094 (10)0.78587 (11)0.0518 (4)
C300.66763 (11)0.10499 (9)0.57041 (10)0.0457 (3)
C310.75828 (11)0.06109 (9)0.61032 (10)0.0449 (3)
C320.81696 (10)0.11489 (9)0.67389 (10)0.0445 (3)
C330.91680 (12)0.09982 (11)0.73823 (13)0.0622 (4)
C340.78353 (12)0.02544 (10)0.58886 (11)0.0530 (4)
C350.59606 (11)0.25134 (9)0.58848 (9)0.0440 (3)
C360.49359 (11)0.23166 (10)0.58115 (10)0.0492 (4)
C371.40543 (17)0.58097 (12)0.69558 (15)0.0789 (6)
C380.70983 (15)0.07119 (11)0.51481 (14)0.0693 (5)
H31.2317 (12)0.4798 (11)0.6272 (12)0.058 (5)*
H61.0502 (13)0.4445 (12)0.6046 (12)0.065 (5)*
H70.8991 (15)0.4051 (12)0.5057 (14)0.074 (6)*
H80.8740 (17)0.2639 (13)0.4604 (15)0.090 (7)*
H90.9993 (16)0.1670 (13)0.5117 (15)0.081 (6)*
H101.1528 (14)0.2042 (11)0.6072 (12)0.065 (5)*
H111.1547 (12)0.2798 (11)0.8425 (11)0.052 (4)*
H121.1241 (15)0.1514 (12)0.9118 (14)0.075 (6)*
H141.3204 (14)0.0298 (12)0.7861 (13)0.072 (5)*
H151.3515 (14)0.1574 (11)0.7157 (13)0.063 (5)*
H18B1.500 (3)0.293 (2)0.811 (2)0.150 (12)*
H18A1.4903 (19)0.3596 (16)0.8759 (19)0.109 (8)*
H18C1.434 (2)0.2752 (19)0.879 (2)0.130 (10)*
H190.3468 (15)0.2780 (11)0.5510 (12)0.068 (5)*
H200.3912 (13)0.4164 (11)0.5269 (11)0.058 (4)*
H210.5670 (15)0.4515 (13)0.5413 (14)0.079 (6)*
H220.6901 (15)0.3486 (11)0.5774 (13)0.067 (5)*
H250.9316 (13)0.2794 (11)0.6967 (12)0.060 (5)*
H260.9742 (16)0.3986 (12)0.7926 (14)0.077 (6)*
H280.7091 (15)0.3842 (12)0.8743 (14)0.078 (6)*
H290.6654 (14)0.2622 (11)0.7844 (12)0.060 (5)*
H300.6122 (12)0.0842 (9)0.5231 (11)0.049 (4)*
H33A0.97110.11460.70770.093*
H33B0.92240.04130.75550.093*
H33C0.92120.13380.79310.093*
H360.4747 (12)0.1753 (11)0.5935 (11)0.055 (4)*
H37A1.45700.62260.71710.118*
H37B1.34080.60110.70510.118*
H37C1.40120.57070.63040.118*
H38A0.73260.12820.51050.104*
H38B0.70600.04320.45610.104*
H38C0.64360.07150.53030.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0427 (6)0.0492 (7)0.0442 (6)0.0012 (5)0.0095 (5)0.0001 (5)
N20.0369 (6)0.0406 (6)0.0450 (6)0.0009 (5)0.0039 (5)0.0007 (5)
F10.1262 (11)0.0598 (7)0.1184 (10)0.0166 (7)0.0336 (8)0.0226 (6)
F20.1027 (9)0.0770 (8)0.1093 (9)0.0133 (7)0.0067 (7)0.0438 (7)
O20.0616 (8)0.0902 (10)0.1176 (12)0.0258 (7)0.0031 (8)0.0064 (9)
O40.0659 (8)0.0554 (7)0.1073 (10)0.0211 (6)0.0001 (7)0.0034 (7)
C10.0602 (10)0.0610 (10)0.0716 (11)0.0120 (8)0.0265 (9)0.0135 (8)
C20.0485 (8)0.0524 (9)0.0542 (8)0.0058 (7)0.0182 (7)0.0064 (7)
C30.0550 (9)0.0479 (8)0.0524 (9)0.0001 (7)0.0160 (7)0.0011 (7)
C40.0459 (8)0.0482 (8)0.0433 (7)0.0017 (6)0.0109 (6)0.0017 (6)
C50.0483 (8)0.0532 (8)0.0392 (7)0.0000 (6)0.0102 (6)0.0014 (6)
C60.0544 (9)0.0582 (10)0.0501 (9)0.0040 (7)0.0083 (7)0.0010 (7)
C70.0582 (10)0.0815 (13)0.0555 (10)0.0137 (9)0.0012 (8)0.0001 (9)
C80.0660 (12)0.0915 (15)0.0590 (11)0.0058 (10)0.0107 (9)0.0099 (10)
C90.0844 (13)0.0650 (12)0.0625 (11)0.0060 (10)0.0067 (10)0.0141 (9)
C100.0637 (10)0.0561 (9)0.0504 (9)0.0035 (8)0.0012 (8)0.0063 (7)
C110.0453 (8)0.0513 (9)0.0495 (8)0.0029 (7)0.0094 (7)0.0046 (7)
C120.0561 (10)0.0655 (11)0.0550 (9)0.0143 (8)0.0144 (8)0.0008 (8)
C130.0704 (11)0.0482 (9)0.0662 (10)0.0115 (8)0.0056 (9)0.0057 (8)
C140.0686 (11)0.0480 (9)0.0718 (11)0.0068 (8)0.0095 (9)0.0013 (8)
C150.0529 (9)0.0579 (10)0.0557 (9)0.0052 (7)0.0142 (8)0.0018 (7)
C160.0423 (7)0.0469 (8)0.0426 (7)0.0022 (6)0.0058 (6)0.0014 (6)
C170.0419 (8)0.0578 (9)0.0459 (8)0.0051 (6)0.0122 (6)0.0074 (7)
C180.0497 (10)0.0790 (13)0.0657 (11)0.0039 (9)0.0010 (9)0.0019 (10)
C190.0479 (9)0.0719 (11)0.0541 (9)0.0144 (8)0.0053 (7)0.0058 (8)
C200.0678 (11)0.0650 (11)0.0539 (9)0.0282 (9)0.0055 (8)0.0033 (8)
C210.0797 (13)0.0484 (10)0.0724 (12)0.0124 (9)0.0035 (9)0.0138 (8)
C220.0541 (10)0.0517 (9)0.0674 (11)0.0020 (7)0.0038 (8)0.0126 (8)
C230.0366 (7)0.0436 (7)0.0430 (7)0.0015 (6)0.0029 (6)0.0025 (6)
C240.0399 (7)0.0421 (7)0.0434 (7)0.0005 (6)0.0026 (6)0.0028 (6)
C250.0447 (8)0.0543 (9)0.0555 (9)0.0048 (7)0.0098 (7)0.0002 (7)
C260.0514 (9)0.0579 (10)0.0709 (11)0.0132 (8)0.0038 (8)0.0027 (8)
C270.0652 (11)0.0497 (9)0.0636 (10)0.0029 (8)0.0028 (8)0.0127 (7)
C280.0607 (10)0.0651 (11)0.0635 (10)0.0061 (8)0.0128 (8)0.0140 (8)
C290.0435 (8)0.0547 (9)0.0568 (9)0.0008 (7)0.0094 (7)0.0040 (7)
C300.0420 (8)0.0458 (8)0.0461 (8)0.0005 (6)0.0019 (6)0.0003 (6)
C310.0430 (8)0.0424 (7)0.0489 (8)0.0031 (6)0.0085 (6)0.0037 (6)
C320.0394 (7)0.0448 (8)0.0488 (8)0.0044 (6)0.0075 (6)0.0052 (6)
C330.0473 (9)0.0598 (10)0.0715 (11)0.0093 (7)0.0056 (8)0.0017 (8)
C340.0522 (9)0.0446 (8)0.0627 (9)0.0057 (7)0.0134 (7)0.0029 (7)
C350.0444 (8)0.0453 (8)0.0392 (7)0.0065 (6)0.0014 (6)0.0002 (6)
C360.0455 (8)0.0515 (9)0.0483 (8)0.0039 (7)0.0042 (6)0.0039 (7)
C370.0896 (14)0.0597 (11)0.0930 (14)0.0206 (10)0.0320 (12)0.0083 (10)
C380.0811 (12)0.0476 (9)0.0754 (12)0.0003 (8)0.0077 (10)0.0092 (8)
Geometric parameters (Å, º) top
N1—C171.3723 (19)C10—H100.980 (19)
N1—C41.3978 (19)C22—C211.381 (2)
N1—C161.4350 (19)C22—H220.933 (19)
N2—C321.3737 (18)C19—C201.370 (3)
N2—C231.3961 (18)C19—H190.984 (19)
N2—C241.4340 (19)C34—C381.495 (2)
F2—C271.3541 (19)C25—C261.380 (2)
F1—C131.357 (2)C25—H250.962 (18)
O4—C341.2143 (19)C12—H120.92 (2)
C23—C301.355 (2)C32—C331.488 (2)
C23—C351.4694 (19)C20—C211.373 (3)
C16—C111.380 (2)C20—H200.980 (17)
C16—C151.382 (2)C15—C141.377 (2)
C36—C191.381 (2)C15—H150.937 (19)
C36—C351.390 (2)C1—C371.493 (3)
C36—H360.956 (17)C26—C271.358 (3)
C35—C221.387 (2)C26—H260.93 (2)
C31—C321.382 (2)C27—C281.365 (3)
C31—C301.417 (2)C33—H33A0.9600
C31—C341.462 (2)C33—H33B0.9600
C17—C21.382 (2)C33—H33C0.9600
C17—C181.483 (2)C9—C81.373 (3)
C5—C61.390 (2)C9—H90.92 (2)
C5—C101.393 (2)C18—H18B0.90 (4)
C5—C41.467 (2)C18—H18A0.95 (3)
C30—H300.963 (16)C18—H18C0.95 (3)
C4—C31.358 (2)C14—H140.958 (19)
C2—C31.421 (2)C6—C71.377 (2)
C2—C11.463 (2)C6—H60.948 (19)
C11—C121.379 (2)C21—H210.95 (2)
C11—H110.962 (17)C28—H280.93 (2)
C13—C141.363 (3)C7—C81.370 (3)
C13—C121.365 (3)C7—H70.94 (2)
O2—C11.220 (2)C37—H37A0.9600
C3—H30.968 (17)C37—H37B0.9600
C24—C291.375 (2)C37—H37C0.9600
C24—C251.383 (2)C38—H38A0.9600
C29—C281.379 (2)C38—H38B0.9600
C29—H290.963 (18)C38—H38C0.9600
C10—C91.376 (3)C8—H80.92 (2)
C17—N1—C4109.61 (13)C13—C12—C11118.87 (17)
C17—N1—C16122.84 (12)C13—C12—H12121.4 (12)
C4—N1—C16126.39 (12)C11—C12—H12119.7 (12)
C32—N2—C23109.17 (11)N2—C32—C31107.64 (12)
C32—N2—C24126.22 (12)N2—C32—C33122.50 (13)
C23—N2—C24124.37 (11)C31—C32—C33129.81 (13)
C30—C23—N2107.40 (12)C19—C20—C21119.62 (16)
C30—C23—C35128.36 (13)C19—C20—H20118.1 (10)
N2—C23—C35124.23 (12)C21—C20—H20122.3 (10)
C11—C16—C15120.41 (15)C14—C15—C16120.45 (16)
C11—C16—N1119.20 (13)C14—C15—H15119.1 (11)
C15—C16—N1120.36 (14)C16—C15—H15120.4 (11)
C19—C36—C35120.77 (16)O2—C1—C2123.30 (17)
C19—C36—H36119.8 (10)O2—C1—C37120.00 (16)
C35—C36—H36119.4 (10)C2—C1—C37116.70 (17)
C22—C35—C36118.32 (14)C27—C26—C25118.74 (16)
C22—C35—C23122.98 (14)C27—C26—H26119.9 (12)
C36—C35—C23118.67 (13)C25—C26—H26121.4 (12)
C32—C31—C30107.18 (13)F2—C27—C26118.68 (16)
C32—C31—C34126.79 (13)F2—C27—C28118.48 (17)
C30—C31—C34126.02 (14)C26—C27—C28122.84 (16)
N1—C17—C2107.77 (13)C32—C33—H33A109.5
N1—C17—C18122.03 (15)C32—C33—H33B109.5
C2—C17—C18130.17 (15)H33A—C33—H33B109.5
C6—C5—C10117.62 (15)C32—C33—H33C109.5
C6—C5—C4119.04 (14)H33A—C33—H33C109.5
C10—C5—C4123.18 (14)H33B—C33—H33C109.5
C23—C30—C31108.60 (13)C8—C9—C10120.47 (19)
C23—C30—H30124.7 (9)C8—C9—H9121.1 (13)
C31—C30—H30126.7 (9)C10—C9—H9118.4 (13)
C3—C4—N1106.77 (13)C17—C18—H18B112 (2)
C3—C4—C5128.45 (14)C17—C18—H18A109.4 (15)
N1—C4—C5124.61 (13)H18B—C18—H18A104 (2)
C17—C2—C3106.82 (13)C17—C18—H18C113.8 (17)
C17—C2—C1125.95 (15)H18B—C18—H18C109 (3)
C3—C2—C1127.21 (15)H18A—C18—H18C109 (2)
C12—C11—C16119.30 (16)C13—C14—C15117.79 (16)
C12—C11—H11122.3 (10)C13—C14—H14119.8 (11)
C16—C11—H11118.4 (10)C15—C14—H14122.4 (11)
F1—C13—C14118.25 (17)C7—C6—C5121.03 (17)
F1—C13—C12118.55 (17)C7—C6—H6120.7 (11)
C14—C13—C12123.19 (16)C5—C6—H6118.3 (11)
C4—C3—C2109.03 (14)C20—C21—C22120.69 (18)
C4—C3—H3123.5 (10)C20—C21—H21121.0 (12)
C2—C3—H3127.4 (10)C22—C21—H21118.3 (12)
C29—C24—C25119.90 (14)C27—C28—C29118.25 (17)
C29—C24—N2119.70 (13)C27—C28—H28120.9 (12)
C25—C24—N2120.36 (13)C29—C28—H28120.8 (12)
C24—C29—C28120.41 (16)C8—C7—C6120.51 (18)
C24—C29—H29119.1 (10)C8—C7—H7120.5 (12)
C28—C29—H29120.4 (10)C6—C7—H7119.0 (12)
C9—C10—C5120.91 (17)C1—C37—H37A109.5
C9—C10—H10120.5 (11)C1—C37—H37B109.5
C5—C10—H10118.6 (11)H37A—C37—H37B109.5
C21—C22—C35120.34 (18)C1—C37—H37C109.5
C21—C22—H22120.0 (11)H37A—C37—H37C109.5
C35—C22—H22119.6 (11)H37B—C37—H37C109.5
C20—C19—C36120.24 (17)C34—C38—H38A109.5
C20—C19—H19119.6 (11)C34—C38—H38B109.5
C36—C19—H19120.2 (11)H38A—C38—H38B109.5
O4—C34—C31122.74 (15)C34—C38—H38C109.5
O4—C34—C38119.63 (15)H38A—C38—H38C109.5
C31—C34—C38117.62 (14)H38B—C38—H38C109.5
C26—C25—C24119.83 (16)C7—C8—C9119.46 (18)
C26—C25—H25120.6 (10)C7—C8—H8122.1 (14)
C24—C25—H25119.6 (10)C9—C8—H8118.4 (14)
C32—N2—C23—C300.51 (16)C6—C5—C10—C90.2 (3)
C24—N2—C23—C30175.26 (13)C4—C5—C10—C9175.14 (17)
C32—N2—C23—C35179.57 (13)C36—C35—C22—C210.1 (2)
C24—N2—C23—C355.7 (2)C23—C35—C22—C21177.94 (16)
C17—N1—C16—C11100.50 (17)C35—C36—C19—C200.9 (2)
C4—N1—C16—C1165.85 (19)C32—C31—C34—O42.6 (3)
C17—N1—C16—C1577.38 (19)C30—C31—C34—O4176.33 (16)
C4—N1—C16—C15116.27 (17)C32—C31—C34—C38177.95 (15)
C19—C36—C35—C221.1 (2)C30—C31—C34—C383.1 (2)
C19—C36—C35—C23177.01 (14)C29—C24—C25—C260.1 (2)
C30—C23—C35—C22133.36 (18)N2—C24—C25—C26177.63 (14)
N2—C23—C35—C2245.5 (2)F1—C13—C12—C11178.27 (15)
C30—C23—C35—C3644.7 (2)C14—C13—C12—C110.7 (3)
N2—C23—C35—C36136.44 (15)C16—C11—C12—C130.2 (2)
C4—N1—C17—C20.25 (16)C23—N2—C32—C310.60 (15)
C16—N1—C17—C2168.12 (13)C24—N2—C32—C31175.24 (13)
C4—N1—C17—C18178.13 (16)C23—N2—C32—C33176.99 (14)
C16—N1—C17—C1813.5 (2)C24—N2—C32—C332.4 (2)
N2—C23—C30—C310.21 (16)C30—C31—C32—N20.46 (16)
C35—C23—C30—C31179.22 (14)C34—C31—C32—N2179.56 (14)
C32—C31—C30—C230.15 (17)C30—C31—C32—C33176.89 (15)
C34—C31—C30—C23179.26 (14)C34—C31—C32—C332.2 (3)
C17—N1—C4—C30.02 (16)C36—C19—C20—C210.5 (3)
C16—N1—C4—C3167.83 (13)C11—C16—C15—C140.5 (2)
C17—N1—C4—C5175.62 (13)N1—C16—C15—C14177.39 (15)
C16—N1—C4—C516.5 (2)C17—C2—C1—O22.0 (3)
C6—C5—C4—C330.6 (2)C3—C2—C1—O2179.97 (17)
C10—C5—C4—C3144.69 (17)C17—C2—C1—C37178.43 (16)
C6—C5—C4—N1154.77 (14)C3—C2—C1—C370.5 (2)
C10—C5—C4—N130.0 (2)C24—C25—C26—C271.1 (3)
N1—C17—C2—C30.37 (16)C25—C26—C27—F2179.26 (16)
C18—C17—C2—C3177.84 (18)C25—C26—C27—C281.2 (3)
N1—C17—C2—C1178.68 (14)C5—C10—C9—C80.2 (3)
C18—C17—C2—C10.5 (3)F1—C13—C14—C15178.44 (16)
C15—C16—C11—C120.3 (2)C12—C13—C14—C150.5 (3)
N1—C16—C11—C12177.58 (13)C16—C15—C14—C130.1 (3)
N1—C4—C3—C20.21 (16)C10—C5—C6—C70.5 (2)
C5—C4—C3—C2175.62 (14)C4—C5—C6—C7174.97 (15)
C17—C2—C3—C40.36 (17)C19—C20—C21—C221.5 (3)
C1—C2—C3—C4178.65 (15)C35—C22—C21—C201.2 (3)
C32—N2—C24—C29123.10 (16)F2—C27—C28—C29179.67 (16)
C23—N2—C24—C2950.8 (2)C26—C27—C28—C290.2 (3)
C32—N2—C24—C2559.1 (2)C24—C29—C28—C271.1 (3)
C23—N2—C24—C25127.00 (15)C5—C6—C7—C80.6 (3)
C25—C24—C29—C281.2 (2)C6—C7—C8—C90.2 (3)
N2—C24—C29—C28176.55 (14)C10—C9—C8—C70.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O20.95 (3)2.44 (3)3.012 (3)119 (2)
C33—H33B···O40.962.473.020 (2)116
C11—H11···O4i0.96 (2)2.57 (2)3.477 (3)157 (1)
C25—H25···Cg2ii0.96 (2)2.66 (2)3.514 (2)148 (1)
C12—H12···Cg2iii0.92 (2)2.80 (2)3.687 (3)162 (2)
C26—H26···O4i0.93 (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.
 

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