Crystal structure of 10-[(3-oxo-3H-benzo[f]chromen-1-yl)meth­yl]-2-tri­fluoro­methyl-9a,10-di­hydro­benz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one

Chandra; Kumar., S.; Puttaraju, K.B.; Shivashankar, K.; Mahendra, M.

doi:10.1107/S2056989015014425

Crystal structure of 10-[(3-oxo-3H-benzo[f]chromen-1-yl)methyl]-2-trifluoromethyl-9a,10-dihydrobenz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one

Chandra, S. Kumar., K. B. Puttaraju, K. Shivashankar and M. Mahendra

In the title compound, C₂₅H₁₄F₃N₃O₃, the dihedral angle between the planes of the benz[4,5]imidazo[1,2-a]pyrimidine unit (r.m.s. deviation = 0.035 Å) and the benzochromene ring system (r.m.s. deviation = 0.106 Å) is 72.82 (5)°. In the crystal, molecules are linked by C—H

O interactions, generating [010] C(9) chains. A weak aromatic π–π stacking interaction [centroid–centroid separation = 3.5376 (15) Å] is also observed.

Keywords: crystal structure; fused-ring system; chromene; benzimidazole; pyrimidinone; benzopyrimidine; π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015014425/hb7467sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015014425/hb7467Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015014425/hb7467Isup3.cml Supplementary material

CCDC reference: 1416062

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.057
wR factor = 0.176
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.315 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT242_ALERT_2_G Low       Ueq as Compared to Neighbors for .....        C15 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O11    ..  C2      ..       2.99 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O23    ..  C2      ..       3.01 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         78 Note

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

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

Comment top

The heterocycles containing benzopyrimidine moiety has a variety of biological activities such as analgesic, anti-inflammatory and antimicrobial activities (Moneam et al., 2004 and Bodke et al., 2003). As part of our studies of these systems (Puttaraju et al., 2013), the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), the three fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar; the maximum deviation from the mean plane being -0.084 (2) Å for atom O11. The dihedral angle between the three fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine with the benzochromene moiety is 72.82 (5)°. Benzochromene moiety and fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine derivatives bridged by the carbon atom (C19) and this inter atomic bond conformation is characterized by torsion angles of 116.5 (2)° (C2–N3–C19–C20) and 160.66 (18)° (N3–C19–C20–C26), respectively. The bond lengths and angles are generally within normal ranges and are comparable to a related structure (Chandra et al., 2013). The packing diagram of the molecule exhibits chain when viewed down the b axis as shown in Fig. 2.

Related literature top

For background to benzopyrimidine derivatives, see: Bodke et al. (2003); Moneam et al. (2004). For the synthesis of the title compound, see: Puttaraju et al. (2013). For a related structure, see: Chandra et al. (2013).

Experimental top

The compound was synthesized by microwave irradiation method (Puttaraju et al., 2013). The synthesized compound (yield = 93%, m.p = 228–230 °C) was recrystallized from 1:3 ethyl acetate and chloroform solution to get yellow block shaped crystals.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective diagram of the molecule with 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the molecule viewed down the b axis.

10-[(3-oxo-3H-Benzo[f]chromen-1-yl)methyl]-2-trifluoromethyl-9a,10-dihydrobenz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one top

Crystal data top

C₂₅H₁₄F₃N₃O₃	F(000) = 944
M_r = 461.39	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5020 reflections
a = 9.7665 (5) Å	θ = 2.7–28.3°
b = 7.7950 (4) Å	µ = 0.12 mm⁻¹
c = 27.0602 (16) Å	T = 293 K
β = 95.186 (5)°	Bolck, yellow
V = 2051.66 (19) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	R_int = 0.033
ω and φ scans	θ_max = 28.3°, θ_min = 2.7°
9209 measured reflections	h = −11→12
5020 independent reflections	k = −5→10
2637 reflections with I > 2σ(I)	l = −27→36

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0676P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
5020 reflections	Δρ_max = 0.21 e Å⁻³
308 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (8)

Crystal data top

C₂₅H₁₄F₃N₃O₃	V = 2051.66 (19) Å³
M_r = 461.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7665 (5) Å	µ = 0.12 mm⁻¹
b = 7.7950 (4) Å	T = 293 K
c = 27.0602 (16) Å	0.30 × 0.25 × 0.20 mm
β = 95.186 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2637 reflections with I > 2σ(I)
9209 measured reflections	R_int = 0.033
5020 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
5020 reflections	Δρ_min = −0.19 e Å⁻³
308 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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

	x	y	z	U_iso*/U_eq
F16	−0.06281 (18)	0.8341 (3)	0.10659 (8)	0.1073 (9)
F17	−0.01199 (16)	0.6009 (3)	0.07308 (6)	0.0921 (8)
F18	−0.14200 (15)	0.5991 (3)	0.13215 (7)	0.1024 (9)
O11	0.20544 (19)	0.5442 (3)	0.27911 (6)	0.0737 (8)
O23	0.4824 (2)	1.3933 (2)	0.15054 (8)	0.0862 (9)
O24	0.62445 (19)	1.3111 (2)	0.09616 (7)	0.0628 (7)
N1	0.31775 (19)	0.6564 (2)	0.21634 (7)	0.0455 (6)
N3	0.44740 (17)	0.7624 (2)	0.16034 (6)	0.0409 (6)
N14	0.21121 (18)	0.7121 (2)	0.13481 (7)	0.0463 (6)
C2	0.3181 (2)	0.7104 (3)	0.16781 (8)	0.0410 (7)
C4	0.5313 (2)	0.7441 (3)	0.20479 (8)	0.0447 (7)
C5	0.4513 (2)	0.6770 (3)	0.24038 (9)	0.0478 (8)
C6	0.5044 (3)	0.6466 (3)	0.28881 (9)	0.0618 (9)
C7	0.6405 (3)	0.6880 (4)	0.29999 (10)	0.0739 (11)
C8	0.7211 (3)	0.7556 (4)	0.26516 (11)	0.0725 (11)
C9	0.6678 (2)	0.7831 (3)	0.21638 (10)	0.0592 (9)
C10	0.1990 (3)	0.5950 (3)	0.23595 (9)	0.0545 (8)
C12	0.0819 (3)	0.6013 (3)	0.20043 (9)	0.0587 (9)
C13	0.0939 (2)	0.6575 (3)	0.15344 (9)	0.0515 (8)
C15	−0.0306 (3)	0.6693 (4)	0.11661 (10)	0.0623 (10)
C19	0.4956 (2)	0.7898 (3)	0.11163 (8)	0.0424 (7)
C20	0.5353 (2)	0.9744 (3)	0.10211 (8)	0.0402 (7)
C21	0.4909 (2)	1.0969 (3)	0.13174 (9)	0.0511 (8)
C22	0.5260 (3)	1.2748 (3)	0.12793 (10)	0.0608 (10)
C25	0.6706 (3)	1.1898 (3)	0.06486 (9)	0.0538 (8)
C26	0.6241 (2)	1.0222 (3)	0.06349 (8)	0.0418 (7)
C27	0.6713 (2)	0.9122 (3)	0.02498 (8)	0.0461 (7)
C28	0.7704 (2)	0.9786 (4)	−0.00588 (9)	0.0598 (9)
C29	0.8182 (3)	1.1485 (4)	0.00084 (11)	0.0763 (11)
C30	0.7689 (3)	1.2528 (4)	0.03478 (11)	0.0730 (11)
C31	0.8178 (3)	0.8749 (5)	−0.04365 (11)	0.0803 (13)
C32	0.7698 (3)	0.7147 (5)	−0.05239 (11)	0.0787 (13)
C33	0.6709 (3)	0.6507 (4)	−0.02363 (10)	0.0682 (10)
C34	0.6220 (3)	0.7459 (3)	0.01357 (9)	0.0536 (8)
H6	0.45110	0.60090	0.31240	0.0740*
H7	0.67990	0.66990	0.33210	0.0890*
H8	0.81240	0.78320	0.27460	0.0870*
H9	0.72200	0.82580	0.19270	0.0710*
H12	−0.00350	0.56670	0.20950	0.0700*
H19A	0.42380	0.75540	0.08650	0.0510*
H19B	0.57470	0.71680	0.10830	0.0510*
H21	0.43440	1.06460	0.15600	0.0610*
H29	0.88510	1.18930	−0.01850	0.0920*
H30	0.79970	1.36540	0.03820	0.0880*
H31	0.88380	0.91840	−0.06300	0.0960*
H32	0.80250	0.64810	−0.07730	0.0950*
H33	0.63690	0.54050	−0.02970	0.0820*
H34	0.55460	0.69940	0.03170	0.0640*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F16	0.0900 (14)	0.0943 (15)	0.1297 (18)	0.0138 (11)	−0.0336 (12)	0.0102 (13)
F17	0.0675 (10)	0.1379 (17)	0.0697 (11)	−0.0180 (11)	−0.0005 (8)	−0.0251 (11)
F18	0.0503 (10)	0.1613 (19)	0.0968 (14)	−0.0305 (11)	0.0128 (9)	0.0081 (13)
O11	0.0810 (13)	0.0911 (15)	0.0517 (11)	−0.0130 (11)	0.0211 (9)	0.0169 (11)
O23	0.1251 (18)	0.0480 (11)	0.0847 (15)	0.0111 (11)	0.0045 (13)	−0.0181 (11)
O24	0.0774 (13)	0.0432 (9)	0.0664 (12)	−0.0115 (9)	−0.0012 (10)	0.0027 (9)
N1	0.0509 (11)	0.0471 (11)	0.0396 (10)	−0.0036 (9)	0.0106 (8)	0.0015 (9)
N3	0.0404 (10)	0.0434 (10)	0.0397 (10)	−0.0047 (9)	0.0083 (7)	−0.0002 (9)
N14	0.0429 (10)	0.0540 (12)	0.0426 (10)	−0.0056 (10)	0.0078 (8)	0.0004 (10)
C2	0.0463 (13)	0.0375 (12)	0.0402 (12)	−0.0020 (10)	0.0101 (9)	−0.0008 (10)
C4	0.0462 (13)	0.0448 (13)	0.0435 (12)	0.0003 (11)	0.0068 (10)	−0.0018 (11)
C5	0.0510 (14)	0.0490 (14)	0.0434 (12)	0.0005 (12)	0.0048 (10)	−0.0012 (12)
C6	0.0688 (17)	0.0678 (18)	0.0484 (14)	0.0022 (14)	0.0038 (12)	0.0029 (14)
C7	0.076 (2)	0.090 (2)	0.0520 (16)	0.0069 (17)	−0.0137 (14)	0.0015 (16)
C8	0.0582 (17)	0.086 (2)	0.0704 (19)	0.0014 (16)	−0.0095 (14)	−0.0032 (17)
C9	0.0480 (14)	0.0681 (17)	0.0612 (16)	−0.0014 (13)	0.0038 (12)	−0.0014 (15)
C10	0.0614 (15)	0.0549 (15)	0.0502 (14)	−0.0069 (13)	0.0210 (12)	0.0048 (13)
C12	0.0488 (14)	0.0646 (17)	0.0651 (17)	−0.0092 (13)	0.0189 (12)	0.0038 (14)
C13	0.0443 (13)	0.0544 (15)	0.0574 (15)	−0.0057 (12)	0.0136 (11)	0.0026 (13)
C15	0.0518 (16)	0.076 (2)	0.0597 (17)	−0.0108 (15)	0.0080 (12)	−0.0019 (16)
C19	0.0450 (12)	0.0405 (12)	0.0434 (12)	−0.0041 (10)	0.0128 (9)	−0.0030 (10)
C20	0.0414 (12)	0.0378 (11)	0.0409 (11)	−0.0025 (10)	0.0016 (9)	0.0000 (10)
C21	0.0587 (15)	0.0443 (13)	0.0506 (14)	0.0006 (12)	0.0070 (11)	−0.0034 (12)
C22	0.0789 (19)	0.0460 (15)	0.0558 (16)	0.0076 (14)	−0.0039 (14)	−0.0056 (13)
C25	0.0565 (15)	0.0501 (14)	0.0531 (14)	−0.0076 (12)	−0.0043 (11)	0.0045 (13)
C26	0.0403 (11)	0.0460 (13)	0.0384 (11)	−0.0023 (10)	0.0006 (9)	0.0052 (10)
C27	0.0388 (11)	0.0601 (15)	0.0391 (11)	0.0036 (11)	0.0018 (9)	0.0043 (12)
C28	0.0456 (14)	0.085 (2)	0.0498 (14)	−0.0011 (14)	0.0095 (11)	0.0087 (15)
C29	0.0701 (19)	0.097 (2)	0.0637 (19)	−0.0268 (18)	0.0162 (15)	0.0151 (18)
C30	0.0746 (19)	0.0704 (19)	0.0729 (19)	−0.0324 (16)	0.0013 (15)	0.0196 (17)
C31	0.0624 (18)	0.122 (3)	0.0605 (18)	0.006 (2)	0.0279 (14)	0.005 (2)
C32	0.077 (2)	0.108 (3)	0.0533 (17)	0.024 (2)	0.0178 (15)	−0.0043 (19)
C33	0.081 (2)	0.0726 (19)	0.0519 (15)	0.0111 (15)	0.0106 (14)	−0.0084 (15)
C34	0.0634 (15)	0.0552 (15)	0.0435 (13)	−0.0026 (13)	0.0115 (11)	−0.0066 (12)

Geometric parameters (Å, º) top

F16—C15	1.344 (4)	C21—C22	1.434 (3)
F17—C15	1.320 (3)	C25—C26	1.383 (3)
F18—C15	1.320 (3)	C25—C30	1.402 (4)
O11—C10	1.229 (3)	C26—C27	1.456 (3)
O23—C22	1.207 (3)	C27—C28	1.431 (3)
O24—C22	1.376 (3)	C27—C34	1.407 (3)
O24—C25	1.372 (3)	C28—C29	1.411 (4)
N1—C2	1.379 (3)	C28—C31	1.414 (4)
N1—C5	1.413 (3)	C29—C30	1.348 (4)
N1—C10	1.403 (3)	C31—C32	1.347 (5)
N3—C2	1.359 (3)	C32—C33	1.387 (4)
N3—C4	1.400 (3)	C33—C34	1.371 (4)
N3—C19	1.455 (3)	C6—H6	0.9300
N14—C2	1.311 (3)	C7—H7	0.9300
N14—C13	1.361 (3)	C8—H8	0.9300
C4—C5	1.396 (3)	C9—H9	0.9300
C4—C9	1.376 (3)	C12—H12	0.9300
C5—C6	1.386 (3)	C19—H19A	0.9700
C6—C7	1.375 (4)	C19—H19B	0.9700
C7—C8	1.386 (4)	C21—H21	0.9300
C8—C9	1.391 (4)	C29—H29	0.9300
C10—C12	1.427 (4)	C30—H30	0.9300
C12—C13	1.360 (3)	C31—H31	0.9300
C13—C15	1.504 (4)	C32—H32	0.9300
C19—C20	1.518 (3)	C33—H33	0.9300
C20—C21	1.344 (3)	C34—H34	0.9300
C20—C26	1.465 (3)

F16···N14	2.878 (3)	C32···C22ⁱⁱⁱ	3.386 (4)
F16···C27ⁱ	3.310 (3)	C32···C21ⁱⁱⁱ	3.502 (4)
F17···N14	2.763 (2)	C33···C22ⁱⁱⁱ	3.320 (4)
F17···H30ⁱⁱ	2.7100	C33···O24ⁱⁱⁱ	3.352 (3)
F17···H29ⁱⁱⁱ	2.5900	C33···C30^viii	3.572 (4)
F17···H32^iv	2.8100	C34···C19	3.045 (3)
F18···H9ⁱ	2.8200	C34···C25ⁱⁱⁱ	3.439 (4)
F18···H12	2.4000	C34···C26ⁱⁱⁱ	3.534 (3)
O11···C6	3.015 (3)	C2···H21	3.0100
O11···C2^v	2.991 (3)	C4···H21	2.9400
O11···N1^v	3.035 (3)	C9···H19B	3.0300
O11···N3^v	3.191 (3)	C10···H6	3.0700
O11···C21^v	3.241 (3)	C19···H9	2.9800
O11···C4^v	3.345 (3)	C19···H34	2.3900
O11···C5^v	3.266 (3)	C20···H34	2.8900
O23···N3^vi	2.912 (2)	C22···H7^vii	3.0900
O23···C2^vi	3.006 (3)	C22···H8^vii	2.9500
O23···N1^vi	3.237 (3)	C25···H7^vii	3.0300
O23···C5^vi	3.321 (3)	C27···H19B	2.9500
O23···C19^vi	3.271 (3)	C30···H33^vi	3.0500
O23···C4^vi	3.120 (3)	C33···H30^viii	2.9900
O24···C33ⁱⁱⁱ	3.352 (3)	C34···H19B	2.6600
O11···H6	2.5200	C34···H19A	2.8900
O11···H21^v	2.3300	H6···O11	2.5200
O23···H8^vii	2.8500	H6···C10	3.0700
O24···H7^vii	2.8200	H7···O24^xi	2.8200
N1···O23^viii	3.237 (3)	H7···C22^xi	3.0900
N1···O11^ix	3.035 (3)	H7···C25^xi	3.0300
N3···O23^viii	2.912 (2)	H8···O23^xi	2.8500
N3···O11^ix	3.191 (3)	H8···C22^xi	2.9500
N14···F17	2.763 (2)	H9···F18^x	2.8200
N14···F16	2.878 (3)	H9···C19	2.9800
N3···H21	2.3600	H12···F18	2.4000
N14···H19A	2.5700	H19A···N14	2.5700
C2···O23^viii	3.006 (3)	H19A···C34	2.8900
C2···O11^ix	2.991 (3)	H19A···H34	2.0900
C4···C21	3.389 (3)	H19B···C9	3.0300
C4···O23^viii	3.120 (3)	H19B···C27	2.9500
C4···O11^ix	3.345 (3)	H19B···C34	2.6600
C5···O11^ix	3.266 (3)	H19B···H34	2.0700
C5···O23^viii	3.321 (3)	H21···N3	2.3600
C6···O11	3.015 (3)	H21···C2	3.0100
C9···C20	3.569 (3)	H21···C4	2.9400
C19···C34	3.045 (3)	H21···O11^ix	2.3300
C19···O23^viii	3.271 (3)	H29···H31	2.4300
C20···C9	3.569 (3)	H29···F17ⁱⁱⁱ	2.5900
C21···O11^ix	3.241 (3)	H30···F17^xii	2.7100
C21···C4	3.389 (3)	H30···C33^vi	2.9900
C21···C32ⁱⁱⁱ	3.502 (4)	H31···H29	2.4300
C22···C33ⁱⁱⁱ	3.320 (4)	H32···F17^iv	2.8100
C22···C32ⁱⁱⁱ	3.386 (4)	H33···C30^viii	3.0500
C25···C34ⁱⁱⁱ	3.439 (4)	H34···C19	2.3900
C26···C34ⁱⁱⁱ	3.534 (3)	H34···C20	2.8900
C27···F16^x	3.310 (3)	H34···H19A	2.0900
C30···C33^vi	3.572 (4)	H34···H19B	2.0700

C22—O24—C25	122.07 (19)	C20—C26—C25	115.8 (2)
C2—N1—C5	108.78 (18)	C20—C26—C27	127.4 (2)
C2—N1—C10	122.53 (19)	C25—C26—C27	116.8 (2)
C5—N1—C10	128.7 (2)	C26—C27—C28	118.6 (2)
C2—N3—C4	108.75 (17)	C26—C27—C34	125.1 (2)
C2—N3—C19	124.04 (17)	C28—C27—C34	116.2 (2)
C4—N3—C19	125.53 (16)	C27—C28—C29	119.9 (2)
C2—N14—C13	112.93 (19)	C27—C28—C31	119.9 (3)
N1—C2—N3	108.36 (17)	C29—C28—C31	120.3 (2)
N1—C2—N14	125.54 (19)	C28—C29—C30	121.3 (3)
N3—C2—N14	126.1 (2)	C25—C30—C29	119.3 (3)
N3—C4—C5	108.08 (17)	C28—C31—C32	121.7 (3)
N3—C4—C9	130.8 (2)	C31—C32—C33	118.9 (3)
C5—C4—C9	121.1 (2)	C32—C33—C34	121.6 (3)
N1—C5—C4	106.02 (19)	C27—C34—C33	121.7 (2)
N1—C5—C6	131.8 (2)	C5—C6—H6	122.00
C4—C5—C6	122.1 (2)	C7—C6—H6	122.00
C5—C6—C7	116.1 (2)	C6—C7—H7	119.00
C6—C7—C8	122.5 (3)	C8—C7—H7	119.00
C7—C8—C9	121.1 (3)	C7—C8—H8	119.00
C4—C9—C8	117.0 (2)	C9—C8—H8	119.00
O11—C10—N1	119.8 (2)	C4—C9—H9	122.00
O11—C10—C12	128.3 (3)	C8—C9—H9	121.00
N1—C10—C12	111.9 (2)	C10—C12—H12	120.00
C10—C12—C13	120.6 (2)	C13—C12—H12	120.00
N14—C13—C12	126.4 (2)	N3—C19—H19A	109.00
N14—C13—C15	113.1 (2)	N3—C19—H19B	109.00
C12—C13—C15	120.4 (2)	C20—C19—H19A	109.00
F16—C15—F17	104.7 (2)	C20—C19—H19B	109.00
F16—C15—F18	106.0 (2)	H19A—C19—H19B	108.00
F16—C15—C13	110.7 (2)	C20—C21—H21	118.00
F17—C15—F18	107.5 (2)	C22—C21—H21	118.00
F17—C15—C13	113.5 (2)	C28—C29—H29	119.00
F18—C15—C13	113.8 (2)	C30—C29—H29	119.00
N3—C19—C20	113.66 (18)	C25—C30—H30	120.00
C19—C20—C21	118.11 (19)	C29—C30—H30	120.00
C19—C20—C26	122.60 (19)	C28—C31—H31	119.00
C21—C20—C26	119.3 (2)	C32—C31—H31	119.00
C20—C21—C22	123.5 (2)	C31—C32—H32	121.00
O23—C22—O24	117.3 (2)	C33—C32—H32	121.00
O23—C22—C21	127.3 (3)	C32—C33—H33	119.00
O24—C22—C21	115.4 (2)	C34—C33—H33	119.00
O24—C25—C26	122.8 (2)	C27—C34—H34	119.00
O24—C25—C30	113.4 (2)	C33—C34—H34	119.00
C26—C25—C30	123.8 (2)

C22—O24—C25—C30	178.8 (2)	C10—C12—C13—C15	−178.0 (2)
C25—O24—C22—O23	−173.1 (2)	C10—C12—C13—N14	0.0 (4)
C25—O24—C22—C21	9.3 (3)	N14—C13—C15—F16	−68.0 (3)
C22—O24—C25—C26	−1.3 (4)	C12—C13—C15—F18	−9.0 (4)
C5—N1—C2—N14	−178.9 (2)	N14—C13—C15—F17	49.4 (3)
C10—N1—C2—N3	179.82 (18)	N14—C13—C15—F18	172.8 (2)
C10—N1—C2—N14	0.3 (3)	C12—C13—C15—F16	110.3 (3)
C5—N1—C2—N3	0.7 (2)	C12—C13—C15—F17	−132.3 (3)
C2—N1—C10—O11	178.1 (2)	N3—C19—C20—C26	160.66 (18)
C2—N1—C10—C12	−1.9 (3)	N3—C19—C20—C21	−16.8 (3)
C5—N1—C10—O11	−3.0 (4)	C19—C20—C21—C22	177.3 (2)
C2—N1—C5—C4	−0.2 (2)	C21—C20—C26—C27	−173.5 (2)
C2—N1—C5—C6	178.2 (2)	C19—C20—C26—C25	−169.1 (2)
C10—N1—C5—C4	−179.3 (2)	C19—C20—C26—C27	9.1 (3)
C10—N1—C5—C6	−0.9 (4)	C26—C20—C21—C22	−0.2 (3)
C5—N1—C10—C12	177.1 (2)	C21—C20—C26—C25	8.3 (3)
C19—N3—C2—N14	−15.4 (3)	C20—C21—C22—O23	174.1 (3)
C2—N3—C4—C9	−178.1 (2)	C20—C21—C22—O24	−8.6 (4)
C19—N3—C4—C5	−164.93 (19)	O24—C25—C26—C20	−7.7 (3)
C2—N3—C4—C5	0.7 (2)	O24—C25—C26—C27	173.9 (2)
C2—N3—C19—C20	116.5 (2)	C30—C25—C26—C20	172.2 (2)
C4—N3—C19—C20	−80.0 (2)	C30—C25—C26—C27	−6.2 (4)
C19—N3—C2—N1	165.06 (18)	O24—C25—C30—C29	−177.2 (3)
C19—N3—C4—C9	16.2 (4)	C26—C25—C30—C29	2.9 (4)
C4—N3—C2—N1	−0.8 (2)	C20—C26—C27—C28	−173.0 (2)
C4—N3—C2—N14	178.7 (2)	C20—C26—C27—C34	10.4 (4)
C13—N14—C2—N3	−178.0 (2)	C25—C26—C27—C28	5.2 (3)
C2—N14—C13—C12	−1.6 (3)	C25—C26—C27—C34	−171.4 (2)
C2—N14—C13—C15	176.5 (2)	C26—C27—C28—C29	−1.2 (3)
C13—N14—C2—N1	1.5 (3)	C26—C27—C28—C31	−179.8 (2)
N3—C4—C9—C8	177.6 (2)	C34—C27—C28—C29	175.7 (2)
C5—C4—C9—C8	−1.2 (4)	C34—C27—C28—C31	−2.9 (3)
N3—C4—C5—N1	−0.3 (2)	C26—C27—C34—C33	179.4 (2)
N3—C4—C5—C6	−178.9 (2)	C28—C27—C34—C33	2.7 (4)
C9—C4—C5—N1	178.7 (2)	C27—C28—C29—C30	−2.3 (4)
C9—C4—C5—C6	0.1 (4)	C31—C28—C29—C30	176.3 (3)
C4—C5—C6—C7	0.6 (4)	C27—C28—C31—C32	1.5 (4)
N1—C5—C6—C7	−177.6 (2)	C29—C28—C31—C32	−177.1 (3)
C5—C6—C7—C8	−0.3 (4)	C28—C29—C30—C25	1.6 (4)
C6—C7—C8—C9	−0.8 (5)	C28—C31—C32—C33	0.3 (5)
C7—C8—C9—C4	1.5 (4)	C31—C32—C33—C34	−0.5 (5)
O11—C10—C12—C13	−178.2 (3)	C32—C33—C34—C27	−1.1 (4)
N1—C10—C12—C13	1.7 (3)

Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z; (v) −x+1/2, y−1/2, −z+1/2; (vi) x, y+1, z; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x, y−1, z; (ix) −x+1/2, y+1/2, −z+1/2; (x) x+1, y, z; (xi) −x+3/2, y−1/2, −z+1/2; (xii) x+1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O11^ix	0.93	2.33	3.241 (3)	168

Symmetry code: (ix) −x+1/2, y+1/2, −z+1/2.