5-Chloro-3,6-dimethyl-1-phenyl-1H,4H-pyrano[2,3-c]pyrazol-4-one.

In the title compound, C(14)H(11)ClN(2)O(2), two independent mol-ecules (A and B) comprise the asymmetric unit with the main difference between them being the relative orientation of the pendent phenyl ring with respect to the fused-ring system [dihedral angles = 8.32 (8)° (A) and 28.32 (8)° (B)]. In the crystal, the A mol-ecules are connected into a linear supra-molecular chain along the a axis via C-H⋯O inter-actions and linked to this via C-H⋯Cl inter-actions are the B mol-ecules. The chains are connected into layers in the ab plane by π-π inter-actions between pyrazole (A) and pyran (B) rings, and between pyrazole (B) and pyran (A) rings [centroid-centroid distances = 3.5442 (11) and 3.4022 (10) Å, respectively].

Related literature

For the analgesic and anti-inflammatory activity of pyrano[2,3-c]pyrazole derivatives, see: Kuo et al. (1984 ▶). For the synthesis, see: Gelin et al. (1983 ▶). For the structure of the derivative without a chloro substituent, see: Asiri et al. (2012 ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Orthorhombic,

a = 11.8864 (4) Å

b = 13.6276 (5) Å

c = 31.0273 (10) Å

V = 5025.9 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.40 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.817, T max = 1.000

17994 measured reflections

5796 independent reflections

4522 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.03

5796 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028528/su2466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028528/su2466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028528/su2466Isup3.cml

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

C14H11ClN2O2	F(000) = 2272
Mr = 274.70	Dx = 1.452 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5991 reflections
a = 11.8864 (4) Å	θ = 2.3–27.5°
b = 13.6276 (5) Å	µ = 0.30 mm−1
c = 31.0273 (10) Å	T = 100 K
V = 5025.9 (3) Å3	Prism, colourless
Z = 16	0.40 × 0.20 × 0.20 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	5796 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4522 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −14→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→10
Tmin = 0.817, Tmax = 1.000	l = −23→40
17994 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0556P)2 + 1.8272P] where P = (Fo2 + 2Fc2)/3
5796 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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	0.47784 (4)	0.10807 (4)	0.536902 (15)	0.02329 (13)
Cl2	0.02904 (4)	0.13031 (4)	0.482067 (16)	0.02722 (14)
O1	0.80047 (10)	0.08977 (9)	0.56939 (4)	0.0182 (3)
O2	0.49310 (11)	0.08983 (10)	0.63216 (5)	0.0250 (3)
O3	0.10832 (10)	0.18078 (9)	0.36014 (4)	0.0182 (3)
O4	0.27633 (11)	0.13467 (10)	0.47565 (4)	0.0241 (3)
N1	0.87843 (13)	0.06692 (12)	0.63947 (5)	0.0173 (3)
N2	0.83780 (13)	0.05555 (11)	0.68112 (5)	0.0190 (3)
N3	0.29023 (13)	0.18475 (11)	0.32886 (5)	0.0187 (3)
N4	0.40146 (12)	0.17885 (12)	0.34252 (5)	0.0204 (3)
C1	0.72337 (17)	0.10797 (16)	0.49990 (6)	0.0240 (4)
H1A	0.6531	0.1003	0.4837	0.036*
H1B	0.7769	0.0573	0.4909	0.036*
H1C	0.7553	0.1730	0.4942	0.036*
C2	0.70039 (15)	0.09791 (13)	0.54658 (6)	0.0186 (4)
C3	0.59974 (15)	0.09712 (14)	0.56689 (6)	0.0192 (4)
C4	0.58537 (15)	0.08820 (13)	0.61417 (6)	0.0186 (4)
C5	0.69231 (15)	0.07793 (13)	0.63565 (6)	0.0168 (4)
C6	0.79054 (15)	0.07976 (13)	0.61251 (6)	0.0164 (4)
C7	0.65511 (17)	0.05340 (15)	0.71804 (6)	0.0237 (4)
H7A	0.7022	0.0369	0.7429	0.035*
H7B	0.5990	0.0017	0.7136	0.035*
H7C	0.6169	0.1160	0.7233	0.035*
C8	0.72680 (15)	0.06198 (13)	0.67899 (6)	0.0184 (4)
C9	0.99726 (15)	0.06552 (13)	0.63192 (6)	0.0172 (4)
C10	1.06841 (16)	0.04123 (15)	0.66587 (6)	0.0221 (4)
H10	1.0387	0.0267	0.6936	0.027*
C11	1.18377 (16)	0.03853 (16)	0.65855 (7)	0.0256 (4)
H11	1.2330	0.0215	0.6815	0.031*
C12	1.22826 (16)	0.06032 (15)	0.61829 (7)	0.0235 (4)
H12	1.3072	0.0582	0.6136	0.028*
C13	1.15581 (16)	0.08529 (15)	0.58498 (7)	0.0240 (4)
H13	1.1856	0.1008	0.5574	0.029*
C14	1.04043 (16)	0.08789 (15)	0.59154 (6)	0.0221 (4)
H14	0.9913	0.1048	0.5686	0.027*
C15	−0.07309 (16)	0.17796 (15)	0.39208 (6)	0.0216 (4)
H15A	−0.1128	0.1366	0.4130	0.032*
H15B	−0.0929	0.1574	0.3628	0.032*
H15C	−0.0949	0.2466	0.3963	0.032*
C16	0.05018 (16)	0.16775 (13)	0.39842 (6)	0.0181 (4)
C17	0.10543 (16)	0.15005 (14)	0.43572 (6)	0.0189 (4)
C18	0.22949 (16)	0.14778 (13)	0.44089 (6)	0.0176 (4)
C19	0.28413 (15)	0.16257 (13)	0.39974 (6)	0.0177 (4)
C20	0.22119 (15)	0.17546 (13)	0.36295 (6)	0.0169 (4)
C21	0.50367 (16)	0.15383 (15)	0.41053 (7)	0.0240 (4)
H21A	0.5689	0.1630	0.3916	0.036*
H21B	0.5061	0.0880	0.4232	0.036*
H21C	0.5053	0.2030	0.4336	0.036*
C22	0.39769 (15)	0.16529 (13)	0.38481 (6)	0.0187 (4)
C23	0.26647 (16)	0.19886 (13)	0.28403 (6)	0.0186 (4)
C24	0.34540 (16)	0.24761 (14)	0.25905 (6)	0.0213 (4)
H24	0.4129	0.2716	0.2716	0.026*
C25	0.32434 (17)	0.26094 (15)	0.21537 (6)	0.0257 (4)
H25	0.3779	0.2940	0.1979	0.031*
C26	0.22545 (17)	0.22611 (15)	0.19720 (6)	0.0264 (5)
H26	0.2114	0.2355	0.1673	0.032*
C27	0.14728 (17)	0.17781 (15)	0.22247 (6)	0.0234 (4)
H27	0.0796	0.1542	0.2099	0.028*
C28	0.16698 (16)	0.16358 (15)	0.26614 (6)	0.0218 (4)
H28	0.1134	0.1303	0.2835	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0166 (2)	0.0292 (3)	0.0240 (3)	0.00225 (19)	−0.00503 (18)	−0.0020 (2)
Cl2	0.0242 (3)	0.0396 (3)	0.0178 (2)	−0.0002 (2)	0.00323 (18)	0.0053 (2)
O1	0.0145 (6)	0.0254 (7)	0.0146 (7)	0.0014 (5)	−0.0003 (5)	−0.0012 (5)
O2	0.0145 (7)	0.0334 (8)	0.0270 (8)	0.0006 (6)	0.0026 (6)	−0.0034 (6)
O3	0.0147 (6)	0.0240 (7)	0.0161 (7)	0.0002 (5)	−0.0003 (5)	0.0024 (5)
O4	0.0233 (7)	0.0314 (8)	0.0178 (7)	0.0013 (6)	−0.0047 (5)	0.0031 (6)
N1	0.0139 (7)	0.0234 (8)	0.0146 (8)	−0.0006 (6)	0.0011 (6)	−0.0014 (6)
N2	0.0179 (8)	0.0240 (8)	0.0150 (8)	−0.0006 (7)	0.0027 (6)	−0.0019 (6)
N3	0.0155 (8)	0.0240 (8)	0.0165 (8)	0.0009 (6)	−0.0017 (6)	0.0012 (6)
N4	0.0155 (8)	0.0241 (8)	0.0215 (9)	−0.0006 (7)	−0.0035 (6)	0.0019 (7)
C1	0.0196 (10)	0.0339 (11)	0.0184 (10)	0.0001 (9)	−0.0028 (7)	−0.0002 (8)
C2	0.0164 (9)	0.0207 (9)	0.0187 (9)	0.0021 (8)	−0.0039 (7)	−0.0016 (8)
C3	0.0158 (9)	0.0207 (9)	0.0212 (10)	0.0018 (8)	−0.0041 (7)	−0.0031 (8)
C4	0.0171 (9)	0.0179 (9)	0.0209 (10)	−0.0010 (7)	−0.0010 (7)	−0.0025 (7)
C5	0.0154 (9)	0.0187 (9)	0.0164 (9)	−0.0006 (7)	0.0016 (7)	−0.0025 (7)
C6	0.0169 (9)	0.0165 (9)	0.0159 (9)	−0.0005 (7)	0.0007 (7)	−0.0023 (7)
C7	0.0213 (10)	0.0313 (11)	0.0184 (10)	−0.0020 (8)	0.0042 (8)	−0.0025 (8)
C8	0.0188 (9)	0.0186 (9)	0.0177 (10)	−0.0006 (7)	−0.0009 (7)	−0.0014 (7)
C9	0.0129 (9)	0.0189 (9)	0.0197 (10)	−0.0001 (7)	0.0006 (7)	−0.0040 (7)
C10	0.0175 (9)	0.0316 (11)	0.0172 (10)	−0.0002 (8)	−0.0008 (7)	−0.0026 (8)
C11	0.0179 (10)	0.0354 (11)	0.0237 (11)	0.0016 (9)	−0.0085 (8)	−0.0047 (9)
C12	0.0129 (9)	0.0293 (11)	0.0283 (11)	−0.0003 (8)	−0.0010 (8)	−0.0071 (9)
C13	0.0200 (10)	0.0310 (11)	0.0209 (10)	−0.0020 (8)	0.0022 (8)	−0.0007 (8)
C14	0.0196 (10)	0.0287 (10)	0.0182 (10)	0.0007 (8)	−0.0012 (7)	0.0009 (8)
C15	0.0183 (9)	0.0263 (10)	0.0201 (10)	−0.0006 (8)	−0.0008 (7)	0.0027 (8)
C16	0.0189 (9)	0.0180 (9)	0.0174 (9)	−0.0007 (7)	0.0013 (7)	−0.0008 (7)
C17	0.0204 (10)	0.0197 (9)	0.0167 (9)	−0.0009 (8)	0.0018 (7)	0.0011 (7)
C18	0.0203 (9)	0.0160 (8)	0.0166 (9)	0.0008 (7)	−0.0012 (7)	0.0001 (7)
C19	0.0177 (9)	0.0174 (9)	0.0180 (9)	0.0002 (7)	−0.0025 (7)	0.0008 (7)
C20	0.0163 (9)	0.0163 (8)	0.0182 (9)	0.0012 (7)	0.0005 (7)	0.0002 (7)
C21	0.0182 (10)	0.0300 (11)	0.0239 (11)	−0.0017 (8)	−0.0047 (8)	0.0028 (9)
C22	0.0174 (9)	0.0184 (9)	0.0202 (10)	−0.0014 (7)	−0.0008 (7)	0.0016 (7)
C23	0.0217 (9)	0.0194 (9)	0.0147 (9)	0.0046 (8)	−0.0012 (7)	0.0005 (7)
C24	0.0201 (10)	0.0232 (9)	0.0207 (10)	0.0016 (8)	−0.0002 (7)	−0.0022 (8)
C25	0.0272 (11)	0.0319 (11)	0.0181 (10)	0.0012 (9)	0.0058 (8)	0.0018 (8)
C26	0.0318 (11)	0.0321 (11)	0.0153 (10)	0.0069 (9)	0.0001 (8)	0.0002 (8)
C27	0.0216 (10)	0.0287 (10)	0.0197 (10)	0.0040 (8)	−0.0033 (8)	−0.0020 (8)
C28	0.0200 (10)	0.0268 (10)	0.0185 (10)	0.0013 (8)	0.0001 (7)	0.0022 (8)

Cl1—C3	1.7285 (19)	C10—H10	0.9500
Cl2—C17	1.7218 (19)	C11—C12	1.389 (3)
O1—C6	1.350 (2)	C11—H11	0.9500
O1—C2	1.389 (2)	C12—C13	1.388 (3)
O2—C4	1.231 (2)	C12—H12	0.9500
O3—C20	1.346 (2)	C13—C14	1.387 (3)
O3—C16	1.386 (2)	C13—H13	0.9500
O4—C18	1.227 (2)	C14—H14	0.9500
N1—C6	1.350 (2)	C15—C16	1.485 (3)
N1—N2	1.388 (2)	C15—H15A	0.9800
N1—C9	1.432 (2)	C15—H15B	0.9800
N2—C8	1.324 (2)	C15—H15C	0.9800
N3—C20	1.345 (2)	C16—C17	1.352 (3)
N3—N4	1.391 (2)	C17—C18	1.484 (3)
N3—C23	1.432 (2)	C18—C19	1.447 (3)
N4—C22	1.326 (2)	C19—C20	1.376 (2)
C1—C2	1.480 (3)	C19—C22	1.428 (3)
C1—H1A	0.9800	C21—C22	1.499 (3)
C1—H1B	0.9800	C21—H21A	0.9800
C1—H1C	0.9800	C21—H21B	0.9800
C2—C3	1.352 (3)	C21—H21C	0.9800
C3—C4	1.482 (3)	C23—C24	1.386 (3)
C4—C5	1.442 (3)	C23—C28	1.392 (3)
C5—C6	1.371 (2)	C24—C25	1.390 (3)
C5—C8	1.423 (3)	C24—H24	0.9500
C7—C8	1.486 (3)	C25—C26	1.387 (3)
C7—H7A	0.9800	C25—H25	0.9500
C7—H7B	0.9800	C26—C27	1.382 (3)
C7—H7C	0.9800	C26—H26	0.9500
C9—C14	1.388 (3)	C27—C28	1.389 (3)
C9—C10	1.391 (3)	C27—H27	0.9500
C10—C11	1.390 (3)	C28—H28	0.9500
C6—O1—C2	115.99 (14)	C14—C13—H13	119.6
C20—O3—C16	115.74 (14)	C12—C13—H13	119.6
C6—N1—N2	108.79 (14)	C13—C14—C9	119.50 (18)
C6—N1—C9	131.59 (16)	C13—C14—H14	120.2
N2—N1—C9	119.60 (14)	C9—C14—H14	120.2
C8—N2—N1	107.03 (15)	C16—C15—H15A	109.5
C20—N3—N4	109.56 (15)	C16—C15—H15B	109.5
C20—N3—C23	131.01 (16)	H15A—C15—H15B	109.5
N4—N3—C23	119.42 (15)	C16—C15—H15C	109.5
C22—N4—N3	106.12 (15)	H15A—C15—H15C	109.5
C2—C1—H1A	109.5	H15B—C15—H15C	109.5
C2—C1—H1B	109.5	C17—C16—O3	120.95 (16)
H1A—C1—H1B	109.5	C17—C16—C15	127.54 (17)
C2—C1—H1C	109.5	O3—C16—C15	111.49 (15)
H1A—C1—H1C	109.5	C16—C17—C18	125.37 (17)
H1B—C1—H1C	109.5	C16—C17—Cl2	119.11 (15)
C3—C2—O1	121.32 (17)	C18—C17—Cl2	115.51 (14)
C3—C2—C1	128.32 (17)	O4—C18—C19	126.34 (18)
O1—C2—C1	110.36 (15)	O4—C18—C17	123.30 (17)
C2—C3—C4	124.33 (17)	C19—C18—C17	110.36 (16)
C2—C3—Cl1	119.35 (15)	C20—C19—C22	103.99 (16)
C4—C3—Cl1	116.32 (14)	C20—C19—C18	120.39 (17)
O2—C4—C5	125.28 (18)	C22—C19—C18	135.59 (17)
O2—C4—C3	123.38 (17)	O3—C20—N3	123.50 (16)
C5—C4—C3	111.33 (16)	O3—C20—C19	127.05 (17)
C6—C5—C8	104.63 (16)	N3—C20—C19	109.44 (16)
C6—C5—C4	120.46 (17)	C22—C21—H21A	109.5
C8—C5—C4	134.88 (17)	C22—C21—H21B	109.5
O1—C6—N1	124.03 (16)	H21A—C21—H21B	109.5
O1—C6—C5	126.54 (16)	C22—C21—H21C	109.5
N1—C6—C5	109.41 (16)	H21A—C21—H21C	109.5
C8—C7—H7A	109.5	H21B—C21—H21C	109.5
C8—C7—H7B	109.5	N4—C22—C19	110.89 (16)
H7A—C7—H7B	109.5	N4—C22—C21	120.85 (17)
C8—C7—H7C	109.5	C19—C22—C21	128.26 (17)
H7A—C7—H7C	109.5	C24—C23—C28	121.18 (17)
H7B—C7—H7C	109.5	C24—C23—N3	118.27 (17)
N2—C8—C5	110.14 (16)	C28—C23—N3	120.55 (17)
N2—C8—C7	121.71 (17)	C23—C24—C25	119.05 (18)
C5—C8—C7	128.14 (17)	C23—C24—H24	120.5
C14—C9—C10	120.74 (17)	C25—C24—H24	120.5
C14—C9—N1	120.63 (16)	C26—C25—C24	120.27 (19)
C10—C9—N1	118.63 (17)	C26—C25—H25	119.9
C11—C10—C9	118.84 (18)	C24—C25—H25	119.9
C11—C10—H10	120.6	C27—C26—C25	120.13 (19)
C9—C10—H10	120.6	C27—C26—H26	119.9
C12—C11—C10	121.11 (18)	C25—C26—H26	119.9
C12—C11—H11	119.4	C26—C27—C28	120.43 (19)
C10—C11—H11	119.4	C26—C27—H27	119.8
C11—C12—C13	119.08 (18)	C28—C27—H27	119.8
C11—C12—H12	120.5	C27—C28—C23	118.95 (18)
C13—C12—H12	120.5	C27—C28—H28	120.5
C14—C13—C12	120.71 (19)	C23—C28—H28	120.5
C6—N1—N2—C8	−0.26 (19)	C10—C9—C14—C13	0.4 (3)
C9—N1—N2—C8	178.57 (16)	N1—C9—C14—C13	−179.52 (17)
C20—N3—N4—C22	0.45 (19)	C20—O3—C16—C17	−0.6 (2)
C23—N3—N4—C22	−179.61 (16)	C20—O3—C16—C15	178.27 (15)
C6—O1—C2—C3	0.9 (2)	O3—C16—C17—C18	3.4 (3)
C6—O1—C2—C1	−179.75 (15)	C15—C16—C17—C18	−175.20 (18)
O1—C2—C3—C4	0.3 (3)	O3—C16—C17—Cl2	−177.84 (13)
C1—C2—C3—C4	−178.98 (18)	C15—C16—C17—Cl2	3.5 (3)
O1—C2—C3—Cl1	179.71 (13)	C16—C17—C18—O4	177.47 (18)
C1—C2—C3—Cl1	0.5 (3)	Cl2—C17—C18—O4	−1.3 (2)
C2—C3—C4—O2	178.32 (18)	C16—C17—C18—C19	−2.8 (3)
Cl1—C3—C4—O2	−1.1 (2)	Cl2—C17—C18—C19	178.44 (13)
C2—C3—C4—C5	−1.5 (3)	O4—C18—C19—C20	179.30 (18)
Cl1—C3—C4—C5	179.05 (13)	C17—C18—C19—C20	−0.4 (2)
O2—C4—C5—C6	−178.18 (18)	O4—C18—C19—C22	1.6 (3)
C3—C4—C5—C6	1.6 (2)	C17—C18—C19—C22	−178.2 (2)
O2—C4—C5—C8	4.2 (3)	C16—O3—C20—N3	178.86 (16)
C3—C4—C5—C8	−176.02 (19)	C16—O3—C20—C19	−2.8 (3)
C2—O1—C6—N1	177.20 (16)	N4—N3—C20—O3	178.15 (15)
C2—O1—C6—C5	−0.7 (3)	C23—N3—C20—O3	−1.8 (3)
N2—N1—C6—O1	−177.71 (15)	N4—N3—C20—C19	−0.4 (2)
C9—N1—C6—O1	3.6 (3)	C23—N3—C20—C19	179.65 (17)
N2—N1—C6—C5	0.5 (2)	C22—C19—C20—O3	−178.29 (17)
C9—N1—C6—C5	−178.13 (18)	C18—C19—C20—O3	3.3 (3)
C8—C5—C6—O1	177.63 (16)	C22—C19—C20—N3	0.2 (2)
C4—C5—C6—O1	−0.6 (3)	C18—C19—C20—N3	−178.16 (16)
C8—C5—C6—N1	−0.5 (2)	N3—N4—C22—C19	−0.3 (2)
C4—C5—C6—N1	−178.81 (16)	N3—N4—C22—C21	178.95 (16)
N1—N2—C8—C5	−0.1 (2)	C20—C19—C22—N4	0.1 (2)
N1—N2—C8—C7	−179.79 (16)	C18—C19—C22—N4	178.07 (19)
C6—C5—C8—N2	0.4 (2)	C20—C19—C22—C21	−179.13 (18)
C4—C5—C8—N2	178.28 (19)	C18—C19—C22—C21	−1.1 (3)
C6—C5—C8—C7	−179.94 (18)	C20—N3—C23—C24	152.03 (19)
C4—C5—C8—C7	−2.0 (3)	N4—N3—C23—C24	−27.9 (2)
C6—N1—C9—C14	6.0 (3)	C20—N3—C23—C28	−28.5 (3)
N2—N1—C9—C14	−172.56 (16)	N4—N3—C23—C28	151.54 (17)
C6—N1—C9—C10	−173.99 (18)	C28—C23—C24—C25	−0.2 (3)
N2—N1—C9—C10	7.5 (2)	N3—C23—C24—C25	179.24 (17)
C14—C9—C10—C11	−0.8 (3)	C23—C24—C25—C26	0.2 (3)
N1—C9—C10—C11	179.18 (17)	C24—C25—C26—C27	−0.1 (3)
C9—C10—C11—C12	0.5 (3)	C25—C26—C27—C28	−0.1 (3)
C10—C11—C12—C13	0.1 (3)	C26—C27—C28—C23	0.1 (3)
C11—C12—C13—C14	−0.5 (3)	C24—C23—C28—C27	0.0 (3)
C12—C13—C14—C9	0.2 (3)	N3—C23—C28—C27	−179.40 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.32	3.203 (2)	154
C14—H14···Cl2i	0.95	2.74	3.448 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.32	3.203 (2)	154
C14—H14⋯Cl2i	0.95	2.74	3.448 (2)	132

Symmetry code: (i) .