Crystal structure and the DFT and MEP study of 4-benzyl-2-[2-(4-fluoro­phen­yl)-2-oxoeth­yl]-6-phenyl­pyridazin-3(2H)-one

The title pyridazin-3(2H)-one derivative, crystallizes with two independent mol­ecules in the asymmetric unit. The two mol­ecules differ essentially in the orientation of the benzyl ring with respect to the central pyridazine ring; this dihedral angle being 3.70 (9) ° in one mol­ecule and 10.47 (8) ° in the other.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.108
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5817
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      24.42 Degree
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2A      --C12A     .        5.5 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C24A Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C22B Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C24B Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C25B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C1A Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C20A Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C20B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C23B Check
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C20B      -C25B     .       1.36 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C1A      -C6A             1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15B     ..F1B      .       2.56 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.706 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.582         87 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.67 mm
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-Benzyl-2-[2-(4-fluorophenyl)-2-oxoethyl]-6-phenylpyridazin-3(2H)-one

Crystal data

C25H19FN2O2	Z = 4
Mr = 398.42	F(000) = 832
Triclinic, P1	Dx = 1.348 Mg m^−3
a = 5.0575 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0973 (7) Å	Cell parameters from 17316 reflections
c = 38.608 (2) Å	θ = 1.1–25.0°
α = 86.237 (5)°	µ = 0.09 mm^−1
β = 86.675 (5)°	T = 296 K
γ = 88.354 (5)°	Prism, colourless
V = 1963.4 (2) Å^3	0.67 × 0.53 × 0.44 mm

Data collection

Stoe IPDS 2 diffractometer	6363 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4315 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.031
Detector resolution: 6.67 pixels mm^-1	θmax = 24.4°, θmin = 1.1°
rotation method scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
Tmin = 0.953, Tmax = 0.974	l = −44→44
16344 measured 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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0633P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
6363 reflections	Δρmax = 0.16 e Å^−3
542 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: (SHELXL2018; Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0116 (12)

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.

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

	x	y	z	Uiso*/Ueq
F1A	0.6289 (5)	0.09624 (17)	−0.02980 (4)	0.1608 (8)
O1A	0.1611 (3)	0.54893 (15)	0.06085 (4)	0.0884 (4)
O2A	0.1102 (3)	0.46400 (14)	0.14261 (3)	0.0843 (4)
N1A	0.4405 (3)	0.59106 (15)	0.11746 (4)	0.0671 (4)
N2A	0.5835 (3)	0.70263 (15)	0.11242 (4)	0.0647 (4)
C1A	0.5570 (7)	0.1845 (3)	−0.00606 (7)	0.1070 (9)
C2A	0.3566 (7)	0.2716 (3)	−0.01297 (6)	0.1131 (9)
H2A	0.267897	0.269609	−0.033355	0.136*
C3A	0.2873 (5)	0.3632 (2)	0.01093 (6)	0.0928 (7)
H3A	0.147897	0.423052	0.006716	0.111*
C4A	0.4204 (4)	0.36847 (19)	0.04125 (5)	0.0682 (5)
C5A	0.6218 (5)	0.2767 (2)	0.04710 (6)	0.0879 (6)
H5A	0.713023	0.277567	0.067316	0.105*
C6A	0.6904 (6)	0.1834 (3)	0.02333 (7)	0.1084 (8)
H6A	0.825601	0.120960	0.027461	0.130*
C7A	0.3491 (4)	0.47327 (19)	0.06528 (5)	0.0674 (5)
C8A	0.5252 (4)	0.48597 (19)	0.09515 (5)	0.0716 (5)
H8A	0.528879	0.402357	0.109027	0.086*
H8B	0.704330	0.502655	0.085854	0.086*
C9A	0.2332 (4)	0.56748 (19)	0.14188 (5)	0.0668 (5)
C10A	0.1890 (4)	0.67082 (19)	0.16591 (4)	0.0643 (5)
C11A	0.3298 (3)	0.78185 (19)	0.16100 (4)	0.0638 (4)
H11A	0.296983	0.849831	0.175921	0.077*
C12A	0.5292 (3)	0.79793 (17)	0.13333 (4)	0.0590 (4)
C13A	0.6973 (3)	0.91648 (17)	0.12757 (4)	0.0592 (4)
C14A	0.9022 (4)	0.9212 (2)	0.10193 (5)	0.0701 (5)
H14A	0.930936	0.850425	0.087826	0.084*
C15A	1.0634 (4)	1.0296 (2)	0.09714 (5)	0.0785 (5)
H15A	1.198796	1.031103	0.079764	0.094*
C16A	1.0263 (4)	1.1351 (2)	0.11770 (5)	0.0771 (5)
H16A	1.135777	1.207810	0.114378	0.093*
C17A	0.8272 (4)	1.1320 (2)	0.14305 (5)	0.0800 (6)
H17A	0.801440	1.202863	0.157184	0.096*
C18A	0.6631 (4)	1.02435 (19)	0.14795 (5)	0.0737 (5)
H18A	0.527209	1.024344	0.165248	0.088*
C19A	−0.0153 (4)	0.6428 (2)	0.19543 (5)	0.0776 (5)
H19A	−0.189465	0.665208	0.187160	0.093*
H19B	−0.010103	0.548385	0.201910	0.093*
C20A	0.0200 (4)	0.7165 (2)	0.22721 (5)	0.0748 (5)
C21A	−0.1352 (5)	0.8225 (3)	0.23581 (7)	0.1061 (8)
H21A	−0.268536	0.853174	0.221492	0.127*
C22A	−0.0946 (9)	0.8864 (3)	0.26656 (11)	0.1434 (13)
H22A	−0.200439	0.959078	0.272578	0.172*
C23A	0.1034 (11)	0.8396 (5)	0.28740 (9)	0.1518 (19)
H23A	0.131088	0.880473	0.307731	0.182*
C24A	0.2553 (8)	0.7361 (5)	0.27864 (8)	0.1443 (14)
H24	0.390783	0.705923	0.292665	0.173*
C25A	0.2138 (5)	0.6744 (3)	0.24941 (6)	0.1052 (8)
H25A	0.319992	0.600939	0.244112	0.126*
F1B	−0.1157 (4)	−0.40818 (14)	0.53084 (4)	0.1266 (5)
O1B	0.3487 (3)	0.07220 (14)	0.43808 (3)	0.0772 (4)
O2B	0.4021 (3)	0.03214 (13)	0.35481 (3)	0.0802 (4)
N1B	0.0734 (3)	0.15026 (13)	0.38207 (3)	0.0584 (4)
N2B	−0.0726 (3)	0.26127 (13)	0.38851 (3)	0.0555 (3)
C1B	−0.0437 (5)	−0.3100 (2)	0.50691 (5)	0.0843 (6)
C2B	0.1540 (5)	−0.2291 (2)	0.51344 (5)	0.0873 (6)
H2B	0.242165	−0.240984	0.533934	0.105*
C3B	0.2203 (4)	−0.1293 (2)	0.48904 (5)	0.0751 (5)
H3B	0.356166	−0.073010	0.493036	0.090*
C4B	0.0889 (3)	−0.11043 (16)	0.45843 (4)	0.0563 (4)
C5B	−0.1091 (4)	−0.19582 (19)	0.45264 (5)	0.0710 (5)
H5B	−0.198472	−0.184832	0.432219	0.085*
C6B	−0.1761 (5)	−0.2978 (2)	0.47698 (6)	0.0842 (6)
H6B	−0.307935	−0.356518	0.473060	0.101*
C7B	0.1617 (3)	0.00317 (17)	0.43376 (4)	0.0573 (4)
C8B	−0.0105 (3)	0.03345 (16)	0.40320 (4)	0.0611 (4)
H8C	−0.004029	−0.042157	0.388888	0.073*
H8D	−0.192703	0.046919	0.411803	0.073*
C9B	0.2882 (3)	0.14027 (18)	0.35847 (4)	0.0601 (4)
C10B	0.3580 (3)	0.26374 (17)	0.33930 (4)	0.0562 (4)
C11B	0.2149 (3)	0.37419 (17)	0.34604 (4)	0.0561 (4)
H11B	0.261247	0.454364	0.334336	0.067*
C12B	−0.0065 (3)	0.37147 (16)	0.37073 (4)	0.0514 (4)
C13B	−0.1834 (3)	0.48873 (15)	0.37667 (4)	0.0525 (4)
C14B	−0.3844 (3)	0.48391 (18)	0.40284 (4)	0.0616 (4)
H14B	−0.402871	0.407558	0.417523	0.074*
C15B	−0.5563 (4)	0.59007 (18)	0.40738 (5)	0.0690 (5)
H15B	−0.689600	0.584914	0.425007	0.083*
C16B	−0.5320 (4)	0.70395 (19)	0.38596 (5)	0.0683 (5)
H16B	−0.648412	0.775698	0.389098	0.082*
C17B	−0.3363 (4)	0.71117 (18)	0.36007 (5)	0.0688 (5)
H17B	−0.319755	0.787943	0.345510	0.083*
C18B	−0.1626 (4)	0.60469 (17)	0.35541 (4)	0.0643 (5)
H18B	−0.029726	0.610886	0.337740	0.077*
C19B	0.5868 (3)	0.2626 (2)	0.31260 (4)	0.0663 (5)
H19C	0.697238	0.184128	0.317408	0.080*
H19D	0.693213	0.339614	0.314856	0.080*
C20B	0.5043 (3)	0.26336 (16)	0.27574 (4)	0.0559 (4)
C21B	0.6112 (5)	0.3470 (2)	0.25011 (5)	0.0966 (7)
H21B	0.740478	0.405093	0.255303	0.116*
C22B	0.5316 (6)	0.3476 (3)	0.21622 (6)	0.1098 (9)
H22B	0.606266	0.407224	0.199291	0.132*
C23B	0.3522 (5)	0.2651 (2)	0.20764 (5)	0.0839 (6)
H23B	0.302079	0.265730	0.184825	0.101*
C24B	0.2429 (6)	0.1804 (3)	0.23227 (6)	0.1173 (9)
H24B	0.115371	0.122164	0.226601	0.141*
C25B	0.3195 (5)	0.1796 (3)	0.26598 (6)	0.1101 (9)
H25B	0.242238	0.119871	0.282659	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.256 (2)	0.1202 (12)	0.1074 (11)	−0.0320 (13)	0.0419 (12)	−0.0539 (9)
O1A	0.0780 (9)	0.0997 (11)	0.0865 (9)	0.0114 (9)	−0.0045 (7)	−0.0049 (8)
O2A	0.0967 (10)	0.0754 (9)	0.0813 (9)	−0.0261 (8)	−0.0038 (7)	−0.0001 (7)
N1A	0.0673 (9)	0.0631 (9)	0.0712 (9)	−0.0060 (8)	−0.0003 (8)	−0.0088 (7)
N2A	0.0624 (9)	0.0636 (9)	0.0682 (9)	−0.0079 (8)	−0.0010 (7)	−0.0053 (7)
C1A	0.161 (3)	0.0827 (17)	0.0773 (15)	−0.0335 (18)	0.0291 (16)	−0.0238 (13)
C2A	0.164 (3)	0.104 (2)	0.0745 (15)	−0.040 (2)	−0.0073 (16)	−0.0167 (14)
C3A	0.1055 (17)	0.0920 (15)	0.0825 (14)	−0.0137 (13)	−0.0141 (13)	−0.0050 (12)
C4A	0.0727 (12)	0.0679 (12)	0.0635 (11)	−0.0170 (10)	0.0053 (9)	−0.0026 (9)
C5A	0.1025 (17)	0.0828 (14)	0.0793 (13)	0.0020 (13)	−0.0038 (12)	−0.0167 (11)
C6A	0.130 (2)	0.0906 (17)	0.1048 (19)	0.0070 (15)	0.0092 (16)	−0.0282 (14)
C7A	0.0631 (11)	0.0694 (12)	0.0683 (11)	−0.0107 (10)	0.0063 (9)	0.0019 (9)
C8A	0.0708 (12)	0.0643 (11)	0.0806 (12)	−0.0020 (10)	−0.0027 (10)	−0.0144 (9)
C9A	0.0694 (12)	0.0662 (12)	0.0649 (10)	−0.0094 (10)	−0.0080 (9)	0.0020 (9)
C10A	0.0600 (10)	0.0739 (12)	0.0588 (10)	−0.0085 (10)	−0.0055 (8)	0.0013 (9)
C11A	0.0615 (11)	0.0700 (12)	0.0601 (10)	−0.0042 (9)	−0.0003 (8)	−0.0082 (8)
C12A	0.0568 (10)	0.0637 (11)	0.0567 (9)	0.0001 (9)	−0.0029 (8)	−0.0060 (8)
C13A	0.0563 (10)	0.0643 (11)	0.0574 (9)	−0.0026 (8)	−0.0050 (8)	−0.0041 (8)
C14A	0.0710 (12)	0.0773 (12)	0.0627 (10)	−0.0117 (10)	0.0048 (9)	−0.0126 (9)
C15A	0.0725 (13)	0.0916 (15)	0.0711 (11)	−0.0194 (11)	0.0082 (9)	−0.0056 (11)
C16A	0.0745 (13)	0.0764 (13)	0.0816 (13)	−0.0196 (11)	−0.0055 (11)	−0.0057 (11)
C17A	0.0854 (14)	0.0706 (13)	0.0855 (13)	−0.0117 (11)	0.0015 (11)	−0.0189 (10)
C18A	0.0726 (12)	0.0714 (12)	0.0769 (12)	−0.0078 (10)	0.0097 (10)	−0.0130 (10)
C19A	0.0666 (12)	0.0979 (15)	0.0677 (11)	−0.0175 (11)	0.0021 (9)	−0.0003 (10)
C20A	0.0664 (12)	0.0952 (15)	0.0616 (11)	−0.0213 (11)	0.0083 (9)	0.0020 (10)
C21A	0.0987 (18)	0.1080 (19)	0.1115 (19)	−0.0175 (16)	0.0124 (15)	−0.0148 (16)
C22A	0.171 (3)	0.115 (2)	0.143 (3)	−0.046 (2)	0.055 (3)	−0.041 (2)
C23A	0.202 (5)	0.181 (4)	0.077 (2)	−0.119 (4)	0.030 (2)	−0.023 (2)
C24A	0.154 (3)	0.216 (4)	0.0664 (18)	−0.082 (3)	−0.0151 (17)	0.010 (2)
C25A	0.0970 (17)	0.147 (2)	0.0718 (14)	−0.0226 (16)	−0.0119 (12)	0.0078 (14)
F1B	0.1881 (15)	0.0904 (9)	0.0925 (9)	−0.0023 (10)	0.0239 (9)	0.0314 (7)
O1B	0.0677 (8)	0.0835 (9)	0.0804 (8)	−0.0159 (7)	−0.0044 (7)	0.0024 (7)
O2B	0.0885 (9)	0.0646 (8)	0.0843 (9)	0.0185 (7)	0.0103 (7)	−0.0045 (6)
N1B	0.0605 (8)	0.0512 (8)	0.0615 (8)	0.0053 (7)	0.0018 (7)	0.0024 (6)
N2B	0.0564 (8)	0.0535 (8)	0.0558 (7)	0.0056 (7)	−0.0021 (6)	−0.0003 (6)
C1B	0.1186 (18)	0.0606 (12)	0.0675 (12)	0.0130 (13)	0.0217 (12)	0.0125 (10)
C2B	0.1173 (18)	0.0800 (15)	0.0631 (12)	0.0123 (14)	−0.0109 (12)	0.0060 (11)
C3B	0.0839 (13)	0.0732 (12)	0.0685 (11)	0.0027 (11)	−0.0118 (10)	−0.0017 (10)
C4B	0.0579 (10)	0.0538 (10)	0.0558 (9)	0.0083 (8)	0.0043 (8)	−0.0035 (8)
C5B	0.0781 (13)	0.0672 (12)	0.0667 (11)	−0.0060 (10)	−0.0023 (9)	0.0029 (9)
C6B	0.0966 (15)	0.0675 (12)	0.0861 (14)	−0.0106 (11)	0.0060 (12)	0.0074 (11)
C7B	0.0521 (10)	0.0572 (10)	0.0616 (9)	0.0049 (9)	0.0050 (8)	−0.0062 (8)
C8B	0.0610 (10)	0.0523 (10)	0.0688 (10)	0.0017 (8)	−0.0030 (8)	0.0033 (8)
C9B	0.0604 (11)	0.0611 (11)	0.0586 (9)	0.0077 (9)	−0.0038 (8)	−0.0063 (8)
C10B	0.0531 (9)	0.0658 (11)	0.0500 (8)	0.0006 (8)	−0.0049 (7)	−0.0051 (8)
C11B	0.0561 (10)	0.0578 (10)	0.0537 (9)	−0.0020 (8)	−0.0030 (7)	0.0012 (7)
C12B	0.0527 (9)	0.0532 (9)	0.0484 (8)	−0.0009 (8)	−0.0059 (7)	−0.0011 (7)
C13B	0.0546 (9)	0.0530 (9)	0.0505 (8)	−0.0001 (8)	−0.0078 (7)	−0.0035 (7)
C14B	0.0657 (11)	0.0610 (10)	0.0565 (9)	0.0048 (9)	0.0023 (8)	0.0004 (8)
C15B	0.0708 (12)	0.0685 (12)	0.0660 (10)	0.0085 (10)	0.0074 (9)	−0.0053 (9)
C16B	0.0672 (12)	0.0640 (11)	0.0738 (11)	0.0137 (9)	−0.0071 (9)	−0.0103 (9)
C17B	0.0788 (12)	0.0541 (10)	0.0721 (11)	0.0045 (9)	−0.0055 (10)	0.0042 (8)
C18B	0.0653 (11)	0.0602 (11)	0.0653 (10)	0.0023 (9)	0.0041 (8)	0.0031 (8)
C19B	0.0555 (10)	0.0838 (13)	0.0593 (10)	0.0040 (9)	0.0005 (8)	−0.0065 (9)
C20B	0.0521 (9)	0.0577 (10)	0.0571 (9)	0.0021 (8)	0.0056 (8)	−0.0074 (8)
C21B	0.1225 (19)	0.0981 (16)	0.0714 (13)	−0.0528 (15)	−0.0054 (12)	−0.0004 (11)
C22B	0.166 (3)	0.0959 (17)	0.0681 (13)	−0.0511 (18)	−0.0095 (14)	0.0116 (12)
C23B	0.1031 (16)	0.0903 (15)	0.0592 (11)	0.0007 (13)	−0.0068 (11)	−0.0107 (11)
C24B	0.129 (2)	0.158 (2)	0.0696 (14)	−0.0650 (19)	−0.0042 (13)	−0.0204 (15)
C25B	0.135 (2)	0.134 (2)	0.0635 (13)	−0.0703 (18)	0.0033 (13)	−0.0048 (13)

Geometric parameters (Å, º)

F1A—C1A	1.348 (3)	F1B—C1B	1.353 (2)
O1A—C7A	1.215 (2)	O1B—C7B	1.217 (2)
O2A—C9A	1.229 (2)	O2B—C9B	1.232 (2)
N1A—N2A	1.353 (2)	N1B—N2B	1.3532 (17)
N1A—C9A	1.384 (2)	N1B—C9B	1.383 (2)
N1A—C8A	1.450 (2)	N1B—C8B	1.449 (2)
N2A—C12A	1.309 (2)	N2B—C12B	1.310 (2)
C1A—C2A	1.349 (4)	C1B—C2B	1.354 (3)
C1A—C6A	1.353 (4)	C1B—C6B	1.366 (3)
C2A—C3A	1.373 (3)	C2B—C3B	1.369 (3)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.389 (3)	C3B—C4B	1.389 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.375 (3)	C4B—C5B	1.378 (3)
C4A—C7A	1.476 (3)	C4B—C7B	1.483 (2)
C5A—C6A	1.382 (3)	C5B—C6B	1.384 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.512 (3)	C7B—C8B	1.517 (2)
C8A—H8A	0.9700	C8B—H8C	0.9700
C8A—H8B	0.9700	C8B—H8D	0.9700
C9A—C10A	1.445 (3)	C9B—C10B	1.449 (2)
C10A—C11A	1.342 (2)	C10B—C11B	1.344 (2)
C10A—C19A	1.511 (3)	C10B—C19B	1.505 (2)
C11A—C12A	1.430 (2)	C11B—C12B	1.427 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.486 (2)	C12B—C13B	1.485 (2)
C13A—C18A	1.386 (3)	C13B—C18B	1.388 (2)
C13A—C14A	1.391 (2)	C13B—C14B	1.391 (2)
C14A—C15A	1.379 (3)	C14B—C15B	1.374 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.372 (3)	C15B—C16B	1.376 (3)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.363 (3)	C16B—C17B	1.365 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.383 (3)	C17B—C18B	1.383 (2)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.498 (3)	C19B—C20B	1.505 (2)
C19A—H19A	0.9700	C19B—H19C	0.9700
C19A—H19B	0.9700	C19B—H19D	0.9700
C20A—C21A	1.356 (3)	C20B—C21B	1.356 (3)
C20A—C25A	1.379 (3)	C20B—C25B	1.363 (3)
C21A—C22A	1.416 (5)	C21B—C22B	1.391 (3)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.375 (5)	C22B—C23B	1.320 (3)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—C24A	1.329 (6)	C23B—C24B	1.342 (3)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.354 (4)	C24B—C25B	1.378 (3)
C24A—H24	0.9300	C24B—H24B	0.9300
C25A—H25A	0.9300	C25B—H25B	0.9300
N2A—N1A—C9A	126.89 (15)	N2B—N1B—C9B	126.71 (14)
N2A—N1A—C8A	114.62 (14)	N2B—N1B—C8B	113.92 (13)
C9A—N1A—C8A	118.45 (16)	C9B—N1B—C8B	119.37 (13)
C12A—N2A—N1A	117.72 (14)	C12B—N2B—N1B	117.52 (13)
F1A—C1A—C2A	118.3 (3)	F1B—C1B—C2B	119.3 (2)
F1A—C1A—C6A	118.9 (3)	F1B—C1B—C6B	117.6 (2)
C2A—C1A—C6A	122.9 (2)	C2B—C1B—C6B	123.07 (19)
C1A—C2A—C3A	118.2 (2)	C1B—C2B—C3B	118.2 (2)
C1A—C2A—H2A	120.9	C1B—C2B—H2B	120.9
C3A—C2A—H2A	120.9	C3B—C2B—H2B	120.9
C2A—C3A—C4A	121.5 (2)	C2B—C3B—C4B	121.3 (2)
C2A—C3A—H3A	119.2	C2B—C3B—H3B	119.3
C4A—C3A—H3A	119.2	C4B—C3B—H3B	119.3
C5A—C4A—C3A	117.84 (19)	C5B—C4B—C3B	118.68 (17)
C5A—C4A—C7A	122.41 (18)	C5B—C4B—C7B	122.54 (16)
C3A—C4A—C7A	119.72 (19)	C3B—C4B—C7B	118.75 (17)
C4A—C5A—C6A	120.9 (2)	C4B—C5B—C6B	120.48 (19)
C4A—C5A—H5A	119.6	C4B—C5B—H5B	119.8
C6A—C5A—H5A	119.6	C6B—C5B—H5B	119.8
C1A—C6A—C5A	118.7 (3)	C1B—C6B—C5B	118.3 (2)
C1A—C6A—H6A	120.6	C1B—C6B—H6B	120.9
C5A—C6A—H6A	120.6	C5B—C6B—H6B	120.9
O1A—C7A—C4A	121.70 (18)	O1B—C7B—C4B	121.68 (16)
O1A—C7A—C8A	121.01 (17)	O1B—C7B—C8B	120.65 (16)
C4A—C7A—C8A	117.26 (17)	C4B—C7B—C8B	117.65 (16)
N1A—C8A—C7A	113.57 (16)	N1B—C8B—C7B	112.24 (15)
N1A—C8A—H8A	108.9	N1B—C8B—H8C	109.2
C7A—C8A—H8A	108.9	C7B—C8B—H8C	109.2
N1A—C8A—H8B	108.9	N1B—C8B—H8D	109.2
C7A—C8A—H8B	108.9	C7B—C8B—H8D	109.2
H8A—C8A—H8B	107.7	H8C—C8B—H8D	107.9
O2A—C9A—N1A	120.46 (17)	O2B—C9B—N1B	120.15 (16)
O2A—C9A—C10A	125.55 (18)	O2B—C9B—C10B	125.22 (16)
N1A—C9A—C10A	113.95 (17)	N1B—C9B—C10B	114.63 (14)
C11A—C10A—C9A	119.16 (16)	C11B—C10B—C9B	118.57 (15)
C11A—C10A—C19A	124.93 (17)	C11B—C10B—C19B	122.85 (16)
C9A—C10A—C19A	115.91 (17)	C9B—C10B—C19B	118.58 (15)
C10A—C11A—C12A	121.47 (17)	C10B—C11B—C12B	121.60 (15)
C10A—C11A—H11A	119.3	C10B—C11B—H11B	119.2
C12A—C11A—H11A	119.3	C12B—C11B—H11B	119.2
N2A—C12A—C11A	120.52 (17)	N2B—C12B—C11B	120.95 (14)
N2A—C12A—C13A	115.78 (15)	N2B—C12B—C13B	115.81 (14)
C11A—C12A—C13A	123.59 (16)	C11B—C12B—C13B	123.17 (14)
C18A—C13A—C14A	117.33 (17)	C18B—C13B—C14B	117.53 (15)
C18A—C13A—C12A	121.94 (16)	C18B—C13B—C12B	121.44 (14)
C14A—C13A—C12A	120.70 (16)	C14B—C13B—C12B	120.96 (14)
C15A—C14A—C13A	120.89 (18)	C15B—C14B—C13B	121.11 (16)
C15A—C14A—H14A	119.6	C15B—C14B—H14B	119.4
C13A—C14A—H14A	119.6	C13B—C14B—H14B	119.4
C16A—C15A—C14A	120.77 (18)	C14B—C15B—C16B	120.31 (17)
C16A—C15A—H15A	119.6	C14B—C15B—H15B	119.8
C14A—C15A—H15A	119.6	C16B—C15B—H15B	119.8
C17A—C16A—C15A	119.18 (19)	C17B—C16B—C15B	119.71 (17)
C17A—C16A—H16A	120.4	C17B—C16B—H16B	120.1
C15A—C16A—H16A	120.4	C15B—C16B—H16B	120.1
C16A—C17A—C18A	120.60 (19)	C16B—C17B—C18B	120.22 (17)
C16A—C17A—H17A	119.7	C16B—C17B—H17B	119.9
C18A—C17A—H17A	119.7	C18B—C17B—H17B	119.9
C17A—C18A—C13A	121.23 (18)	C17B—C18B—C13B	121.11 (16)
C17A—C18A—H18A	119.4	C17B—C18B—H18B	119.4
C13A—C18A—H18A	119.4	C13B—C18B—H18B	119.4
C20A—C19A—C10A	114.86 (17)	C10B—C19B—C20B	113.81 (14)
C20A—C19A—H19A	108.6	C10B—C19B—H19C	108.8
C10A—C19A—H19A	108.6	C20B—C19B—H19C	108.8
C20A—C19A—H19B	108.6	C10B—C19B—H19D	108.8
C10A—C19A—H19B	108.6	C20B—C19B—H19D	108.8
H19A—C19A—H19B	107.5	H19C—C19B—H19D	107.7
C21A—C20A—C25A	117.7 (2)	C21B—C20B—C25B	115.85 (18)
C21A—C20A—C19A	122.8 (2)	C21B—C20B—C19B	121.93 (17)
C25A—C20A—C19A	119.5 (2)	C25B—C20B—C19B	122.22 (17)
C20A—C21A—C22A	120.1 (3)	C20B—C21B—C22B	121.4 (2)
C20A—C21A—H21A	120.0	C20B—C21B—H21B	119.3
C22A—C21A—H21A	120.0	C22B—C21B—H21B	119.3
C23A—C22A—C21A	119.1 (4)	C23B—C22B—C21B	121.2 (2)
C23A—C22A—H22A	120.4	C23B—C22B—H22B	119.4
C21A—C22A—H22A	120.4	C21B—C22B—H22B	119.4
C24A—C23A—C22A	120.3 (4)	C22B—C23B—C24B	119.1 (2)
C24A—C23A—H23A	119.8	C22B—C23B—H23B	120.4
C22A—C23A—H23A	119.8	C24B—C23B—H23B	120.4
C23A—C24A—C25A	120.3 (4)	C23B—C24B—C25B	120.1 (2)
C23A—C24A—H24	119.8	C23B—C24B—H24B	120.0
C25A—C24A—H24	119.8	C25B—C24B—H24B	120.0
C24A—C25A—C20A	122.4 (3)	C20B—C25B—C24B	122.4 (2)
C24A—C25A—H25A	118.8	C20B—C25B—H25B	118.8
C20A—C25A—H25A	118.8	C24B—C25B—H25B	118.8
C9A—N1A—N2A—C12A	2.5 (2)	C9B—N1B—N2B—C12B	0.1 (2)
C8A—N1A—N2A—C12A	−175.39 (15)	C8B—N1B—N2B—C12B	179.13 (14)
F1A—C1A—C2A—C3A	−178.7 (2)	F1B—C1B—C2B—C3B	−179.03 (18)
C6A—C1A—C2A—C3A	0.4 (4)	C6B—C1B—C2B—C3B	1.1 (3)
C1A—C2A—C3A—C4A	0.9 (4)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—C3A—C4A—C5A	−1.4 (3)	C2B—C3B—C4B—C5B	−1.0 (3)
C2A—C3A—C4A—C7A	176.6 (2)	C2B—C3B—C4B—C7B	177.23 (17)
C3A—C4A—C5A—C6A	0.6 (3)	C3B—C4B—C5B—C6B	0.3 (3)
C7A—C4A—C5A—C6A	−177.3 (2)	C7B—C4B—C5B—C6B	−177.79 (16)
F1A—C1A—C6A—C5A	177.9 (2)	F1B—C1B—C6B—C5B	178.42 (17)
C2A—C1A—C6A—C5A	−1.1 (4)	C2B—C1B—C6B—C5B	−1.7 (3)
C4A—C5A—C6A—C1A	0.6 (4)	C4B—C5B—C6B—C1B	0.9 (3)
C5A—C4A—C7A—O1A	−175.73 (19)	C5B—C4B—C7B—O1B	−174.93 (16)
C3A—C4A—C7A—O1A	6.4 (3)	C3B—C4B—C7B—O1B	7.0 (2)
C5A—C4A—C7A—C8A	6.3 (3)	C5B—C4B—C7B—C8B	6.8 (2)
C3A—C4A—C7A—C8A	−171.63 (18)	C3B—C4B—C7B—C8B	−171.34 (15)
N2A—N1A—C8A—C7A	−102.78 (18)	N2B—N1B—C8B—C7B	−99.93 (16)
C9A—N1A—C8A—C7A	79.2 (2)	C9B—N1B—C8B—C7B	79.18 (19)
O1A—C7A—C8A—N1A	2.1 (3)	O1B—C7B—C8B—N1B	−1.2 (2)
C4A—C7A—C8A—N1A	−179.88 (15)	C4B—C7B—C8B—N1B	177.16 (13)
N2A—N1A—C9A—O2A	176.25 (16)	N2B—N1B—C9B—O2B	−179.01 (16)
C8A—N1A—C9A—O2A	−5.9 (3)	C8B—N1B—C9B—O2B	2.0 (2)
N2A—N1A—C9A—C10A	−6.1 (3)	N2B—N1B—C9B—C10B	0.2 (2)
C8A—N1A—C9A—C10A	171.72 (15)	C8B—N1B—C9B—C10B	−178.76 (14)
O2A—C9A—C10A—C11A	−176.77 (17)	O2B—C9B—C10B—C11B	179.82 (17)
N1A—C9A—C10A—C11A	5.7 (2)	N1B—C9B—C10B—C11B	0.6 (2)
O2A—C9A—C10A—C19A	3.9 (3)	O2B—C9B—C10B—C19B	0.1 (3)
N1A—C9A—C10A—C19A	−173.59 (16)	N1B—C9B—C10B—C19B	−179.12 (14)
C9A—C10A—C11A—C12A	−2.4 (3)	C9B—C10B—C11B—C12B	−1.8 (2)
C19A—C10A—C11A—C12A	176.84 (17)	C19B—C10B—C11B—C12B	177.96 (15)
N1A—N2A—C12A—C11A	1.6 (2)	N1B—N2B—C12B—C11B	−1.2 (2)
N1A—N2A—C12A—C13A	177.97 (13)	N1B—N2B—C12B—C13B	175.68 (13)
C10A—C11A—C12A—N2A	−1.5 (3)	C10B—C11B—C12B—N2B	2.2 (2)
C10A—C11A—C12A—C13A	−177.60 (15)	C10B—C11B—C12B—C13B	−174.52 (15)
N2A—C12A—C13A—C18A	−179.53 (16)	N2B—C12B—C13B—C18B	−168.90 (15)
C11A—C12A—C13A—C18A	−3.3 (3)	C11B—C12B—C13B—C18B	8.0 (2)
N2A—C12A—C13A—C14A	−1.6 (2)	N2B—C12B—C13B—C14B	8.0 (2)
C11A—C12A—C13A—C14A	174.69 (17)	C11B—C12B—C13B—C14B	−175.11 (16)
C18A—C13A—C14A—C15A	−0.1 (3)	C18B—C13B—C14B—C15B	0.1 (3)
C12A—C13A—C14A—C15A	−178.21 (17)	C12B—C13B—C14B—C15B	−176.92 (16)
C13A—C14A—C15A—C16A	0.3 (3)	C13B—C14B—C15B—C16B	−0.1 (3)
C14A—C15A—C16A—C17A	−0.1 (3)	C14B—C15B—C16B—C17B	0.1 (3)
C15A—C16A—C17A—C18A	−0.4 (3)	C15B—C16B—C17B—C18B	−0.2 (3)
C16A—C17A—C18A—C13A	0.6 (3)	C16B—C17B—C18B—C13B	0.2 (3)
C14A—C13A—C18A—C17A	−0.3 (3)	C14B—C13B—C18B—C17B	−0.2 (3)
C12A—C13A—C18A—C17A	177.72 (17)	C12B—C13B—C18B—C17B	176.83 (16)
C11A—C10A—C19A—C20A	−24.3 (3)	C11B—C10B—C19B—C20B	−78.2 (2)
C9A—C10A—C19A—C20A	154.93 (18)	C9B—C10B—C19B—C20B	101.59 (18)
C10A—C19A—C20A—C21A	104.7 (2)	C10B—C19B—C20B—C21B	132.6 (2)
C10A—C19A—C20A—C25A	−76.8 (2)	C10B—C19B—C20B—C25B	−47.9 (3)
C25A—C20A—C21A—C22A	0.4 (3)	C25B—C20B—C21B—C22B	1.1 (4)
C19A—C20A—C21A—C22A	178.9 (2)	C19B—C20B—C21B—C22B	−179.4 (2)
C20A—C21A—C22A—C23A	0.0 (4)	C20B—C21B—C22B—C23B	−1.2 (4)
C21A—C22A—C23A—C24A	0.4 (5)	C21B—C22B—C23B—C24B	0.8 (4)
C22A—C23A—C24A—C25A	−1.1 (5)	C22B—C23B—C24B—C25B	−0.4 (4)
C23A—C24A—C25A—C20A	1.5 (5)	C21B—C20B—C25B—C24B	−0.7 (4)
C21A—C20A—C25A—C24A	−1.1 (4)	C19B—C20B—C25B—C24B	179.8 (2)
C19A—C20A—C25A—C24A	−179.7 (2)	C23B—C24B—C25B—C20B	0.4 (5)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the N1A/N2A/C9A–C12A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15A—H15A···F1A^i	0.93	2.49	3.263 (3)	141
C15B—H15B···F1B^ii	0.93	2.56	3.310 (3)	138
C8A—H8B···O1A^iii	0.97	2.50	3.466 (3)	179
C8B—H8D···O1B^iv	0.97	2.49	3.458 (2)	176
C19A—H19A···Cg1^iv	0.97	2.93	3.845 (2)	158

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