4-{[5-(4-Chloro-phen-yl)-1-(4-fluoro-phen-yl)-1H-pyrazol-3-yl]carbon-yl}-N-(4-cyano-phen-yl)piperazine-1-carboxamide.

In the title compound, C(28)H(22)ClFN(6)O(2), the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyano-phenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chloro-phenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, inter-molecular N-H⋯O, C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into sheets parallel to the ac plane.

Related literature

For background to pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For the synthetic procedure, see: Ragavan et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2010 ▶); Shahani et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H22ClFN6O2

M = 528.97

Monoclinic,

a = 9.9221 (3) Å

b = 21.3339 (7) Å

c = 12.7201 (4) Å

β = 111.629 (1)°

V = 2502.97 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.36 × 0.26 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.931, T max = 0.985

19192 measured reflections

5660 independent reflections

4272 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.116

S = 1.07

5660 reflections

347 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.35 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036159/wn2409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036159/wn2409Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H22ClFN6O2	F(000) = 1096
Mr = 528.97	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5338 reflections
a = 9.9221 (3) Å	θ = 2.4–27.3°
b = 21.3339 (7) Å	µ = 0.20 mm−1
c = 12.7201 (4) Å	T = 100 K
β = 111.629 (1)°	Plate, colourless
V = 2502.97 (14) Å3	0.36 × 0.26 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5660 independent reflections
Radiation source: fine-focus sealed tube	4272 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 27.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.931, Tmax = 0.985	k = −27→24
19192 measured reflections	l = −14→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0294P)2 + 2.8225P] where P = (Fo2 + 2Fc2)/3
5660 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.47534 (7)	0.60803 (3)	0.78980 (5)	0.03029 (16)
F1	0.48142 (15)	0.22562 (7)	0.89619 (12)	0.0304 (3)
N1	0.81146 (19)	0.34593 (9)	0.69103 (14)	0.0161 (4)
N2	0.89747 (19)	0.31063 (9)	0.65254 (14)	0.0164 (4)
N3	1.04762 (19)	0.34908 (9)	0.44459 (14)	0.0174 (4)
N4	1.0136 (2)	0.35012 (9)	0.21385 (15)	0.0203 (4)
N5	1.1177 (2)	0.35113 (10)	0.07780 (16)	0.0194 (4)
N6	1.2635 (2)	0.45747 (11)	−0.37105 (17)	0.0335 (5)
O1	1.14153 (16)	0.28689 (7)	0.59902 (12)	0.0193 (3)
O2	0.91589 (17)	0.41027 (8)	0.05706 (13)	0.0236 (4)
C1	0.7918 (2)	0.29390 (11)	0.85563 (18)	0.0197 (5)
H1A	0.8905	0.2999	0.8948	0.024*
C2	0.7083 (2)	0.26399 (11)	0.90742 (19)	0.0220 (5)
H2A	0.7493	0.2503	0.9819	0.026*
C3	0.5637 (2)	0.25525 (11)	0.84547 (19)	0.0216 (5)
C4	0.4962 (2)	0.27504 (11)	0.73509 (19)	0.0228 (5)
H4A	0.3978	0.2681	0.6959	0.027*
C5	0.5800 (2)	0.30562 (11)	0.68465 (18)	0.0203 (5)
H5A	0.5380	0.3200	0.6106	0.024*
C6	0.7266 (2)	0.31466 (10)	0.74509 (18)	0.0163 (5)
C7	0.7134 (2)	0.45597 (11)	0.79798 (18)	0.0209 (5)
H7A	0.7593	0.4246	0.8494	0.025*
C8	0.6372 (2)	0.50256 (11)	0.82822 (19)	0.0227 (5)
H8A	0.6303	0.5021	0.8992	0.027*
C9	0.5715 (2)	0.54962 (11)	0.75187 (19)	0.0213 (5)
C10	0.5806 (2)	0.55132 (11)	0.64628 (19)	0.0218 (5)
H10A	0.5365	0.5835	0.5961	0.026*
C11	0.6562 (2)	0.50443 (11)	0.61567 (18)	0.0194 (5)
H11A	0.6629	0.5054	0.5447	0.023*
C12	0.7220 (2)	0.45589 (11)	0.69021 (18)	0.0177 (5)
C13	0.8020 (2)	0.40700 (11)	0.65574 (17)	0.0166 (5)
C14	0.8854 (2)	0.41079 (11)	0.58986 (17)	0.0176 (5)
H14A	0.9007	0.4460	0.5526	0.021*
C15	0.9423 (2)	0.35043 (11)	0.59080 (17)	0.0163 (5)
C16	1.0502 (2)	0.32613 (10)	0.54447 (17)	0.0157 (4)
C17	1.1727 (2)	0.33981 (11)	0.41143 (18)	0.0192 (5)
H17A	1.2416	0.3120	0.4652	0.023*
H17B	1.2204	0.3797	0.4134	0.023*
C18	1.1283 (2)	0.31192 (11)	0.29329 (17)	0.0205 (5)
H18A	1.2112	0.3107	0.2703	0.025*
H18B	1.0939	0.2694	0.2934	0.025*
C19	0.8884 (2)	0.35880 (11)	0.24632 (18)	0.0202 (5)
H19A	0.8419	0.3187	0.2449	0.024*
H19B	0.8189	0.3861	0.1921	0.024*
C20	0.9325 (2)	0.38715 (11)	0.36402 (17)	0.0195 (5)
H20A	0.9668	0.4297	0.3634	0.023*
H20B	0.8493	0.3886	0.3867	0.023*
C21	1.0089 (2)	0.37302 (11)	0.11281 (18)	0.0179 (5)
C22	1.1497 (2)	0.37577 (11)	−0.01271 (17)	0.0185 (5)
C23	1.2352 (3)	0.33979 (11)	−0.05514 (19)	0.0235 (5)
H23A	1.2688	0.3009	−0.0230	0.028*
C24	1.2707 (3)	0.36094 (12)	−0.1441 (2)	0.0261 (5)
H24A	1.3268	0.3361	−0.1722	0.031*
C25	1.2229 (2)	0.41924 (11)	−0.19194 (18)	0.0204 (5)
C26	1.1417 (3)	0.45604 (12)	−0.1474 (2)	0.0255 (5)
H26A	1.1115	0.4956	−0.1775	0.031*
C27	1.1050 (3)	0.43481 (11)	−0.0591 (2)	0.0247 (5)
H27A	1.0502	0.4600	−0.0304	0.030*
C28	1.2494 (3)	0.44038 (12)	−0.29033 (19)	0.0242 (5)
H1N5	1.148 (3)	0.3133 (14)	0.098 (2)	0.033 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0278 (3)	0.0295 (4)	0.0347 (3)	0.0067 (3)	0.0129 (3)	−0.0071 (3)
F1	0.0281 (8)	0.0372 (9)	0.0311 (8)	−0.0038 (7)	0.0170 (6)	0.0075 (7)
N1	0.0167 (9)	0.0172 (10)	0.0156 (9)	0.0006 (8)	0.0074 (7)	0.0003 (8)
N2	0.0161 (9)	0.0184 (10)	0.0156 (9)	−0.0001 (8)	0.0069 (7)	−0.0017 (8)
N3	0.0154 (9)	0.0217 (10)	0.0151 (9)	0.0004 (8)	0.0056 (7)	0.0006 (8)
N4	0.0192 (10)	0.0268 (11)	0.0163 (9)	0.0060 (8)	0.0081 (7)	0.0040 (8)
N5	0.0244 (11)	0.0174 (11)	0.0190 (9)	0.0042 (9)	0.0110 (8)	0.0024 (8)
N6	0.0404 (13)	0.0391 (14)	0.0255 (11)	−0.0110 (11)	0.0175 (10)	−0.0008 (10)
O1	0.0193 (8)	0.0207 (9)	0.0175 (8)	0.0024 (7)	0.0063 (6)	0.0022 (7)
O2	0.0264 (9)	0.0278 (10)	0.0190 (8)	0.0088 (7)	0.0111 (7)	0.0068 (7)
C1	0.0176 (11)	0.0217 (13)	0.0187 (11)	0.0025 (9)	0.0055 (9)	0.0024 (9)
C2	0.0236 (12)	0.0258 (14)	0.0167 (11)	0.0039 (10)	0.0076 (9)	0.0062 (10)
C3	0.0255 (13)	0.0209 (13)	0.0237 (11)	−0.0025 (10)	0.0153 (10)	0.0007 (10)
C4	0.0152 (11)	0.0278 (14)	0.0241 (12)	−0.0018 (10)	0.0058 (9)	−0.0017 (10)
C5	0.0214 (12)	0.0241 (13)	0.0148 (10)	0.0016 (10)	0.0060 (9)	0.0011 (10)
C6	0.0191 (11)	0.0147 (11)	0.0176 (10)	0.0008 (9)	0.0096 (9)	−0.0004 (9)
C7	0.0233 (12)	0.0220 (13)	0.0165 (10)	0.0017 (10)	0.0062 (9)	−0.0002 (10)
C8	0.0253 (12)	0.0255 (13)	0.0190 (11)	−0.0005 (10)	0.0102 (9)	−0.0040 (10)
C9	0.0162 (11)	0.0194 (12)	0.0279 (12)	−0.0015 (9)	0.0076 (9)	−0.0064 (10)
C10	0.0188 (12)	0.0188 (13)	0.0262 (12)	0.0011 (10)	0.0063 (9)	0.0028 (10)
C11	0.0179 (11)	0.0211 (13)	0.0189 (10)	−0.0033 (9)	0.0064 (8)	−0.0005 (9)
C12	0.0167 (11)	0.0170 (12)	0.0198 (10)	−0.0033 (9)	0.0073 (8)	−0.0043 (9)
C13	0.0172 (11)	0.0173 (12)	0.0131 (10)	−0.0010 (9)	0.0030 (8)	−0.0008 (9)
C14	0.0192 (11)	0.0181 (12)	0.0163 (10)	−0.0030 (9)	0.0076 (9)	−0.0009 (9)
C15	0.0167 (11)	0.0185 (12)	0.0124 (10)	−0.0027 (9)	0.0038 (8)	−0.0016 (9)
C16	0.0160 (11)	0.0164 (12)	0.0139 (10)	−0.0046 (9)	0.0045 (8)	−0.0041 (9)
C17	0.0164 (11)	0.0245 (13)	0.0170 (10)	−0.0016 (9)	0.0066 (9)	0.0003 (10)
C18	0.0201 (12)	0.0274 (13)	0.0154 (10)	0.0049 (10)	0.0083 (9)	0.0025 (10)
C19	0.0177 (11)	0.0265 (13)	0.0165 (10)	0.0026 (10)	0.0064 (9)	0.0027 (10)
C20	0.0192 (11)	0.0226 (13)	0.0176 (10)	0.0035 (10)	0.0080 (9)	0.0020 (9)
C21	0.0185 (11)	0.0184 (12)	0.0164 (10)	−0.0021 (9)	0.0060 (9)	−0.0023 (9)
C22	0.0207 (12)	0.0224 (13)	0.0119 (10)	−0.0030 (10)	0.0056 (8)	−0.0028 (9)
C23	0.0296 (13)	0.0205 (13)	0.0227 (11)	0.0054 (10)	0.0124 (10)	0.0034 (10)
C24	0.0289 (13)	0.0304 (15)	0.0233 (12)	0.0052 (11)	0.0146 (10)	−0.0003 (11)
C25	0.0220 (12)	0.0234 (13)	0.0161 (10)	−0.0040 (10)	0.0076 (9)	−0.0015 (9)
C26	0.0349 (14)	0.0199 (13)	0.0250 (12)	0.0020 (11)	0.0150 (10)	0.0028 (10)
C27	0.0339 (14)	0.0200 (13)	0.0259 (12)	0.0034 (11)	0.0179 (11)	0.0004 (10)
C28	0.0252 (13)	0.0265 (14)	0.0203 (12)	−0.0063 (10)	0.0077 (10)	−0.0034 (10)

Cl1—C9	1.742 (2)	C8—H8A	0.9300
F1—C3	1.367 (2)	C9—C10	1.379 (3)
N1—N2	1.358 (2)	C10—C11	1.389 (3)
N1—C13	1.370 (3)	C10—H10A	0.9300
N1—C6	1.433 (3)	C11—C12	1.393 (3)
N2—C15	1.339 (3)	C11—H11A	0.9300
N3—C16	1.353 (3)	C12—C13	1.472 (3)
N3—C17	1.464 (3)	C13—C14	1.380 (3)
N3—C20	1.467 (3)	C14—C15	1.405 (3)
N4—C21	1.360 (3)	C14—H14A	0.9300
N4—C19	1.458 (3)	C15—C16	1.492 (3)
N4—C18	1.460 (3)	C17—C18	1.523 (3)
N5—C21	1.392 (3)	C17—H17A	0.9700
N5—C22	1.404 (3)	C17—H17B	0.9700
N5—H1N5	0.87 (3)	C18—H18A	0.9700
N6—C28	1.146 (3)	C18—H18B	0.9700
O1—C16	1.241 (3)	C19—C20	1.522 (3)
O2—C21	1.226 (3)	C19—H19A	0.9700
C1—C6	1.386 (3)	C19—H19B	0.9700
C1—C2	1.389 (3)	C20—H20A	0.9700
C1—H1A	0.9300	C20—H20B	0.9700
C2—C3	1.372 (3)	C22—C23	1.392 (3)
C2—H2A	0.9300	C22—C27	1.392 (3)
C3—C4	1.380 (3)	C23—C24	1.380 (3)
C4—C5	1.386 (3)	C23—H23A	0.9300
C4—H4A	0.9300	C24—C25	1.389 (3)
C5—C6	1.386 (3)	C24—H24A	0.9300
C5—H5A	0.9300	C25—C26	1.387 (3)
C7—C8	1.387 (3)	C25—C28	1.443 (3)
C7—C12	1.404 (3)	C26—C27	1.378 (3)
C7—H7A	0.9300	C26—H26A	0.9300
C8—C9	1.382 (3)	C27—H27A	0.9300
N2—N1—C13	112.69 (17)	C15—C14—H14A	127.2
N2—N1—C6	118.25 (17)	N2—C15—C14	111.51 (18)
C13—N1—C6	128.21 (18)	N2—C15—C16	116.95 (19)
C15—N2—N1	104.40 (17)	C14—C15—C16	131.30 (19)
C16—N3—C17	119.79 (18)	O1—C16—N3	121.78 (19)
C16—N3—C20	126.63 (18)	O1—C16—C15	119.71 (18)
C17—N3—C20	113.48 (17)	N3—C16—C15	118.49 (19)
C21—N4—C19	119.10 (18)	N3—C17—C18	111.66 (17)
C21—N4—C18	126.94 (18)	N3—C17—H17A	109.3
C19—N4—C18	113.76 (17)	C18—C17—H17A	109.3
C21—N5—C22	125.0 (2)	N3—C17—H17B	109.3
C21—N5—H1N5	116.6 (18)	C18—C17—H17B	109.3
C22—N5—H1N5	115.4 (18)	H17A—C17—H17B	108.0
C6—C1—C2	119.4 (2)	N4—C18—C17	109.47 (18)
C6—C1—H1A	120.3	N4—C18—H18A	109.8
C2—C1—H1A	120.3	C17—C18—H18A	109.8
C3—C2—C1	118.1 (2)	N4—C18—H18B	109.8
C3—C2—H2A	121.0	C17—C18—H18B	109.8
C1—C2—H2A	121.0	H18A—C18—H18B	108.2
F1—C3—C2	118.2 (2)	N4—C19—C20	111.31 (18)
F1—C3—C4	118.1 (2)	N4—C19—H19A	109.4
C2—C3—C4	123.7 (2)	C20—C19—H19A	109.4
C3—C4—C5	117.8 (2)	N4—C19—H19B	109.4
C3—C4—H4A	121.1	C20—C19—H19B	109.4
C5—C4—H4A	121.1	H19A—C19—H19B	108.0
C6—C5—C4	119.7 (2)	N3—C20—C19	109.55 (18)
C6—C5—H5A	120.2	N3—C20—H20A	109.8
C4—C5—H5A	120.2	C19—C20—H20A	109.8
C5—C6—C1	121.3 (2)	N3—C20—H20B	109.8
C5—C6—N1	118.75 (19)	C19—C20—H20B	109.8
C1—C6—N1	119.91 (19)	H20A—C20—H20B	108.2
C8—C7—C12	120.5 (2)	O2—C21—N4	122.4 (2)
C8—C7—H7A	119.8	O2—C21—N5	122.7 (2)
C12—C7—H7A	119.8	N4—C21—N5	114.94 (19)
C9—C8—C7	119.3 (2)	C23—C22—C27	118.6 (2)
C9—C8—H8A	120.3	C23—C22—N5	117.7 (2)
C7—C8—H8A	120.3	C27—C22—N5	123.6 (2)
C10—C9—C8	121.4 (2)	C24—C23—C22	121.0 (2)
C10—C9—Cl1	119.32 (18)	C24—C23—H23A	119.5
C8—C9—Cl1	119.31 (18)	C22—C23—H23A	119.5
C9—C10—C11	119.3 (2)	C23—C24—C25	120.2 (2)
C9—C10—H10A	120.3	C23—C24—H24A	119.9
C11—C10—H10A	120.3	C25—C24—H24A	119.9
C10—C11—C12	120.7 (2)	C26—C25—C24	119.0 (2)
C10—C11—H11A	119.7	C26—C25—C28	119.8 (2)
C12—C11—H11A	119.7	C24—C25—C28	121.2 (2)
C11—C12—C7	118.8 (2)	C27—C26—C25	121.0 (2)
C11—C12—C13	119.52 (19)	C27—C26—H26A	119.5
C7—C12—C13	121.7 (2)	C25—C26—H26A	119.5
N1—C13—C14	105.71 (19)	C26—C27—C22	120.3 (2)
N1—C13—C12	123.74 (19)	C26—C27—H27A	119.9
C14—C13—C12	130.5 (2)	C22—C27—H27A	119.9
C13—C14—C15	105.69 (19)	N6—C28—C25	176.8 (3)
C13—C14—H14A	127.2
C13—N1—N2—C15	−0.5 (2)	C13—C14—C15—N2	0.4 (2)
C6—N1—N2—C15	169.86 (18)	C13—C14—C15—C16	−173.7 (2)
C6—C1—C2—C3	1.1 (3)	C17—N3—C16—O1	−14.7 (3)
C1—C2—C3—F1	179.8 (2)	C20—N3—C16—O1	169.2 (2)
C1—C2—C3—C4	−0.7 (4)	C17—N3—C16—C15	163.51 (19)
F1—C3—C4—C5	179.3 (2)	C20—N3—C16—C15	−12.6 (3)
C2—C3—C4—C5	−0.2 (4)	N2—C15—C16—O1	−33.1 (3)
C3—C4—C5—C6	0.7 (3)	C14—C15—C16—O1	140.7 (2)
C4—C5—C6—C1	−0.2 (3)	N2—C15—C16—N3	148.6 (2)
C4—C5—C6—N1	179.5 (2)	C14—C15—C16—N3	−37.6 (3)
C2—C1—C6—C5	−0.7 (3)	C16—N3—C17—C18	128.3 (2)
C2—C1—C6—N1	179.6 (2)	C20—N3—C17—C18	−55.1 (3)
N2—N1—C6—C5	−102.4 (2)	C21—N4—C18—C17	130.4 (2)
C13—N1—C6—C5	66.2 (3)	C19—N4—C18—C17	−54.9 (2)
N2—N1—C6—C1	77.3 (3)	N3—C17—C18—N4	53.1 (2)
C13—N1—C6—C1	−114.1 (2)	C21—N4—C19—C20	−128.6 (2)
C12—C7—C8—C9	−1.1 (3)	C18—N4—C19—C20	56.3 (3)
C7—C8—C9—C10	−0.2 (4)	C16—N3—C20—C19	−129.4 (2)
C7—C8—C9—Cl1	179.84 (18)	C17—N3—C20—C19	54.4 (2)
C8—C9—C10—C11	0.6 (3)	N4—C19—C20—N3	−53.7 (2)
Cl1—C9—C10—C11	−179.42 (17)	C19—N4—C21—O2	13.6 (3)
C9—C10—C11—C12	0.3 (3)	C18—N4—C21—O2	−172.0 (2)
C10—C11—C12—C7	−1.5 (3)	C19—N4—C21—N5	−166.6 (2)
C10—C11—C12—C13	−179.7 (2)	C18—N4—C21—N5	7.9 (3)
C8—C7—C12—C11	1.9 (3)	C22—N5—C21—O2	11.2 (3)
C8—C7—C12—C13	−179.9 (2)	C22—N5—C21—N4	−168.7 (2)
N2—N1—C13—C14	0.7 (2)	C21—N5—C22—C23	−164.2 (2)
C6—N1—C13—C14	−168.42 (19)	C21—N5—C22—C27	18.1 (3)
N2—N1—C13—C12	−176.73 (18)	C27—C22—C23—C24	−2.4 (4)
C6—N1—C13—C12	14.1 (3)	N5—C22—C23—C24	179.8 (2)
C11—C12—C13—N1	−148.1 (2)	C22—C23—C24—C25	0.9 (4)
C7—C12—C13—N1	33.7 (3)	C23—C24—C25—C26	1.2 (4)
C11—C12—C13—C14	35.1 (3)	C23—C24—C25—C28	−175.3 (2)
C7—C12—C13—C14	−143.0 (2)	C24—C25—C26—C27	−1.8 (4)
N1—C13—C14—C15	−0.6 (2)	C28—C25—C26—C27	174.8 (2)
C12—C13—C14—C15	176.6 (2)	C25—C26—C27—C22	0.2 (4)
N1—N2—C15—C14	0.0 (2)	C23—C22—C27—C26	1.8 (3)
N1—N2—C15—C16	175.01 (17)	N5—C22—C27—C26	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···O1i	0.87 (3)	2.14 (3)	2.958 (3)	157 (2)
C2—H2A···N2ii	0.93	2.49	3.386 (3)	161
C4—H4A···O1iii	0.93	2.42	3.310 (3)	161
C7—H7A···O2iv	0.93	2.54	3.312 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1N5⋯O1i	0.87 (3)	2.14 (3)	2.958 (3)	157 (2)
C2—H2A⋯N2ii	0.93	2.49	3.386 (3)	161
C4—H4A⋯O1iii	0.93	2.42	3.310 (3)	161
C7—H7A⋯O2iv	0.93	2.54	3.312 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .