Solvatochromism and mechanochromism observed in a tri­phenyl­amine derivative

A donor–π–acceptor fluorescent dye, 4-[N,N-di(4-phenyl)amino]benzaldehyde 4-chloro­benzoyl hydrazone (TPA-CBH), based on a tri­phenyl­amine derivative (TPA) and 4-chloro­benzoyl hydrazine (CBH) was designed and synthesized. The optical properties of this luminogen were investigated in solutions as well as in the solid states. In the intramolecular charge-transfer (CT) mechanism, TPA-CBH exhibits solvatochromism when dissolved in various polar solvents. Aggregation-induced emission was observed with the changes of tetrahydrofuran/water ratios. In the solid state, mechanochromic fluorescence is observed when the samples are stressed under different conditions. Based on structural analyses and theoretical calculations, it is found that intra- and intermolecular CT processes play a key role in the diversity of fluorescent properties.

Computing details

Cell refinement: SAINT v8.34A (Bruker, 2013) for FormA; SAINT V8.38A (?, 2016) for FormB. Data reduction: SAINT v8.34A (Bruker, 2013) for FormA; SAINT V8.38A (?, 2016) for FormB. Program(s) used to solve structure: SIR2004 (Burla et al., 2007) for FormA; SHELXS (Sheldrick, 2008) for FormB. For both structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

TPAP (FormA)

Crystal data

C26H20ClN3O	Z = 4
Mr = 425.90	F(000) = 888
Triclinic, P1	Dx = 1.343 Mg m^−3
a = 10.5741 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5798 (3) Å	Cell parameters from 8768 reflections
c = 16.6564 (4) Å	θ = 2.5–26.9°
α = 107.731 (1)°	µ = 0.21 mm^−1
β = 98.269 (1)°	T = 296 K
γ = 106.980 (1)°	Block, colourless
V = 2106.51 (8) Å^3	0.2 × 0.15 × 0.1 mm

Data collection

Bruker APEX-II CCD diffractometer	7021 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.043
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0638 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9339. The λ/2 correction factor is 0.00150.	θmax = 27.6°, θmin = 1.3°
Tmin = 0.696, Tmax = 0.746	h = −13→13
31002 measured reflections	k = −17→17
9694 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
9694 reflections	Δρmax = 0.29 e Å^−3
559 parameters	Δρmin = −0.43 e Å^−3
0 restraints

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
Cl01	0.72965 (5)	0.61062 (4)	0.10386 (3)	0.04546 (14)
Cl02	0.22157 (6)	0.15345 (6)	0.63910 (4)	0.0701 (2)
O003	0.54623 (13)	0.40715 (11)	0.40262 (9)	0.0378 (3)
O004	1.03322 (13)	0.40452 (11)	0.35801 (9)	0.0389 (3)
N005	0.84701 (16)	0.39996 (12)	0.41247 (10)	0.0336 (4)
H005	0.7820	0.4256	0.4177	0.040*
N006	0.86981 (15)	0.33537 (12)	0.45873 (10)	0.0334 (3)
N007	0.33416 (16)	0.40780 (13)	0.35364 (10)	0.0359 (4)
H007	0.2491	0.3837	0.3530	0.043*
N008	0.34834 (15)	0.73345 (14)	0.04107 (10)	0.0349 (4)
N009	0.77730 (15)	0.04230 (13)	0.70140 (11)	0.0355 (4)
N00A	0.37622 (16)	0.46906 (13)	0.30295 (10)	0.0356 (4)
C00B	0.33183 (17)	0.66467 (15)	0.09006 (12)	0.0284 (4)
C00C	0.23589 (17)	0.75411 (15)	0.00080 (12)	0.0293 (4)
C00D	0.36862 (17)	0.32884 (14)	0.46210 (11)	0.0280 (4)
C00E	0.87273 (17)	0.47293 (14)	0.29887 (11)	0.0280 (4)
C00F	0.30062 (18)	0.53038 (15)	0.19035 (12)	0.0298 (4)
C00G	0.47731 (16)	0.77846 (15)	0.02432 (11)	0.0286 (4)
C00H	1.01630 (18)	0.10232 (15)	0.77699 (11)	0.0303 (4)
H00H	1.0169	0.1741	0.8002	0.036*
C00I	0.44055 (17)	0.68131 (15)	0.15737 (12)	0.0299 (4)
H00I	0.5242	0.7372	0.1690	0.036*
C00J	0.19295 (18)	0.51389 (15)	0.12288 (12)	0.0335 (4)
H00J	0.1097	0.4574	0.1108	0.040*
C00K	0.89822 (17)	0.01780 (15)	0.72188 (12)	0.0303 (4)
C00L	0.72511 (17)	0.26104 (15)	0.62618 (12)	0.0304 (4)
H00L	0.6814	0.3121	0.6384	0.037*
C00M	0.78305 (17)	0.11469 (15)	0.65463 (12)	0.0302 (4)
C00N	0.65263 (18)	−0.01918 (15)	0.71239 (12)	0.0310 (4)
C00O	0.27863 (19)	0.46274 (15)	0.24439 (12)	0.0323 (4)
H00O	0.1910	0.4138	0.2358	0.039*
C00P	0.54503 (18)	0.71009 (15)	−0.01258 (12)	0.0309 (4)
H00P	0.5093	0.6346	−0.0238	0.037*
C00Q	0.72106 (18)	0.19294 (15)	0.67357 (12)	0.0325 (4)
H00Q	0.6767	0.1997	0.7182	0.039*
C00R	0.53200 (18)	0.89109 (16)	0.04129 (13)	0.0348 (4)
H00R	0.4874	0.9374	0.0667	0.042*
C00S	0.21231 (18)	0.73896 (15)	−0.08658 (12)	0.0315 (4)
H00S	0.2676	0.7123	−0.1193	0.038*
C00T	0.42461 (18)	0.61528 (15)	0.20669 (12)	0.0308 (4)
H00T	0.4977	0.6276	0.2515	0.037*
C00U	0.79382 (17)	0.25429 (14)	0.56039 (11)	0.0292 (4)
C00V	0.85657 (18)	0.17571 (16)	0.54212 (12)	0.0332 (4)
H00V	0.9026	0.1699	0.4983	0.040*
C00W	0.69096 (19)	0.50093 (15)	0.21385 (12)	0.0331 (4)
H00W	0.5989	0.4906	0.1967	0.040*
C00X	0.92662 (18)	0.42325 (14)	0.35879 (11)	0.0298 (4)
C00Y	0.42625 (18)	0.38552 (14)	0.40433 (12)	0.0300 (4)
C00Z	0.73480 (18)	0.45844 (15)	0.27380 (12)	0.0322 (4)
H00Z	0.6720	0.4201	0.2974	0.039*
C010	0.85112 (18)	0.10651 (16)	0.58838 (12)	0.0337 (4)
H010	0.8930	0.0542	0.5754	0.040*
C011	0.42792 (18)	0.25710 (16)	0.48075 (12)	0.0345 (4)
H011	0.4999	0.2465	0.4575	0.041*
C012	1.13385 (18)	0.07961 (17)	0.79746 (12)	0.0352 (4)
H012	1.2132	0.1364	0.8348	0.042*
C013	0.96535 (18)	0.53151 (15)	0.26367 (12)	0.0327 (4)
H013	1.0574	0.5414	0.2799	0.039*
C014	0.79513 (18)	0.32829 (15)	0.51239 (12)	0.0324 (4)
H014	0.7405	0.3713	0.5210	0.039*
C015	0.52670 (18)	−0.03106 (16)	0.66388 (12)	0.0343 (4)
H015	0.5236	0.0030	0.6233	0.041*
C016	0.78496 (19)	0.55860 (15)	0.17979 (12)	0.0328 (4)
C017	0.66687 (19)	0.75521 (17)	−0.03279 (12)	0.0374 (4)
H017	0.7129	0.7098	−0.0574	0.045*
C018	0.26116 (18)	0.34484 (15)	0.49730 (12)	0.0336 (4)
H018	0.2193	0.3913	0.4838	0.040*
C019	0.10680 (18)	0.76322 (16)	−0.12588 (12)	0.0342 (4)
H019	0.0920	0.7532	−0.1847	0.041*
C01A	0.20769 (18)	0.58011 (16)	0.07340 (12)	0.0340 (4)
H01A	0.1344	0.5680	0.0289	0.041*
C01B	0.71951 (18)	0.86713 (18)	−0.01646 (14)	0.0408 (5)
H01B	0.8005	0.8969	−0.0305	0.049*
C01C	0.92204 (19)	0.57526 (16)	0.20466 (13)	0.0363 (4)
H01C	0.9847	0.6155	0.1820	0.044*
C01D	0.2166 (2)	0.29137 (17)	0.55255 (12)	0.0391 (5)
H01D	0.1467	0.3034	0.5776	0.047*
C01E	0.65250 (19)	0.93445 (17)	0.02042 (14)	0.0407 (5)
H01E	0.6884	1.0099	0.0315	0.049*
C01F	0.15219 (19)	0.79287 (18)	0.04886 (13)	0.0391 (5)
H01F	0.1671	0.8030	0.1077	0.047*
C01G	0.02389 (19)	0.80206 (17)	−0.07830 (13)	0.0383 (4)
H01G	−0.0468	0.8185	−0.1047	0.046*
C01H	1.1343 (2)	−0.02563 (18)	0.76319 (13)	0.0398 (5)
H01H	1.2131	−0.0404	0.7782	0.048*
C01I	0.27679 (19)	0.22042 (18)	0.56992 (13)	0.0414 (5)
C01J	0.4073 (2)	−0.14657 (17)	0.73357 (14)	0.0418 (5)
H01J	0.3259	−0.1891	0.7403	0.050*
C01K	0.40603 (19)	−0.09315 (17)	0.67542 (13)	0.0386 (4)
H01K	0.3228	−0.0988	0.6434	0.046*
C01L	0.38089 (19)	0.20123 (17)	0.53372 (14)	0.0424 (5)
H01L	0.4189	0.1515	0.5448	0.051*
C01M	0.9002 (2)	−0.08764 (17)	0.68632 (14)	0.0443 (5)
H01M	0.8215	−0.1446	0.6484	0.053*
C01N	0.0463 (2)	0.81648 (19)	0.00923 (13)	0.0444 (5)
H01N	−0.0101	0.8421	0.0415	0.053*
C01O	0.5321 (2)	−0.13580 (17)	0.78193 (14)	0.0451 (5)
H01O	0.5344	−0.1719	0.8211	0.054*
C01P	0.6532 (2)	−0.07191 (17)	0.77251 (13)	0.0408 (5)
H01P	0.7360	−0.0639	0.8066	0.049*
C01Q	1.0182 (2)	−0.10925 (19)	0.70670 (15)	0.0490 (5)
H01Q	1.0189	−0.1804	0.6822	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0544 (3)	0.0504 (3)	0.0477 (3)	0.0288 (2)	0.0134 (2)	0.0299 (3)
Cl02	0.0556 (4)	0.1002 (5)	0.0645 (4)	0.0080 (3)	0.0157 (3)	0.0621 (4)
O003	0.0329 (7)	0.0423 (8)	0.0436 (8)	0.0118 (6)	0.0141 (6)	0.0225 (7)
O004	0.0376 (7)	0.0465 (8)	0.0424 (8)	0.0219 (6)	0.0118 (6)	0.0221 (7)
N005	0.0378 (8)	0.0363 (9)	0.0371 (9)	0.0197 (7)	0.0115 (7)	0.0204 (8)
N006	0.0373 (8)	0.0340 (8)	0.0321 (8)	0.0142 (7)	0.0053 (7)	0.0168 (7)
N007	0.0332 (8)	0.0400 (9)	0.0420 (9)	0.0109 (7)	0.0131 (7)	0.0253 (8)
N008	0.0256 (7)	0.0509 (10)	0.0470 (10)	0.0203 (7)	0.0150 (7)	0.0341 (9)
N009	0.0272 (8)	0.0437 (9)	0.0467 (10)	0.0164 (7)	0.0082 (7)	0.0283 (8)
N00A	0.0393 (9)	0.0373 (9)	0.0400 (9)	0.0145 (7)	0.0151 (7)	0.0240 (8)
C00B	0.0274 (9)	0.0363 (10)	0.0315 (9)	0.0173 (7)	0.0131 (7)	0.0176 (8)
C00C	0.0235 (8)	0.0338 (10)	0.0347 (10)	0.0118 (7)	0.0075 (7)	0.0169 (8)
C00D	0.0277 (9)	0.0260 (9)	0.0262 (9)	0.0058 (7)	0.0040 (7)	0.0089 (8)
C00E	0.0314 (9)	0.0253 (9)	0.0268 (9)	0.0114 (7)	0.0067 (7)	0.0080 (8)
C00F	0.0344 (9)	0.0316 (9)	0.0321 (10)	0.0171 (8)	0.0141 (8)	0.0156 (8)
C00G	0.0226 (8)	0.0401 (10)	0.0301 (9)	0.0135 (7)	0.0067 (7)	0.0202 (8)
C00H	0.0332 (9)	0.0319 (9)	0.0306 (9)	0.0146 (8)	0.0098 (7)	0.0142 (8)
C00I	0.0263 (8)	0.0358 (10)	0.0349 (10)	0.0150 (7)	0.0112 (7)	0.0175 (9)
C00J	0.0296 (9)	0.0347 (10)	0.0363 (10)	0.0084 (8)	0.0088 (8)	0.0160 (9)
C00K	0.0279 (9)	0.0363 (10)	0.0315 (10)	0.0141 (7)	0.0046 (7)	0.0178 (9)
C00L	0.0297 (9)	0.0327 (10)	0.0307 (10)	0.0150 (7)	0.0048 (7)	0.0117 (8)
C00M	0.0250 (8)	0.0357 (10)	0.0323 (10)	0.0117 (7)	0.0031 (7)	0.0168 (8)
C00N	0.0285 (9)	0.0330 (10)	0.0316 (10)	0.0113 (7)	0.0051 (7)	0.0127 (8)
C00O	0.0354 (10)	0.0323 (10)	0.0349 (10)	0.0139 (8)	0.0141 (8)	0.0158 (9)
C00P	0.0292 (9)	0.0346 (10)	0.0316 (10)	0.0132 (7)	0.0056 (7)	0.0149 (8)
C00Q	0.0319 (9)	0.0399 (10)	0.0316 (10)	0.0165 (8)	0.0094 (7)	0.0169 (9)
C00R	0.0334 (10)	0.0365 (10)	0.0409 (11)	0.0188 (8)	0.0071 (8)	0.0177 (9)
C00S	0.0326 (9)	0.0339 (10)	0.0326 (10)	0.0157 (8)	0.0114 (8)	0.0135 (9)
C00T	0.0297 (9)	0.0385 (10)	0.0319 (10)	0.0182 (8)	0.0100 (7)	0.0166 (9)
C00U	0.0260 (8)	0.0314 (9)	0.0262 (9)	0.0078 (7)	−0.0004 (7)	0.0108 (8)
C00V	0.0305 (9)	0.0410 (11)	0.0315 (10)	0.0153 (8)	0.0088 (8)	0.0147 (9)
C00W	0.0304 (9)	0.0375 (10)	0.0359 (10)	0.0172 (8)	0.0097 (8)	0.0140 (9)
C00X	0.0324 (9)	0.0273 (9)	0.0292 (9)	0.0113 (7)	0.0055 (7)	0.0099 (8)
C00Y	0.0311 (9)	0.0264 (9)	0.0309 (10)	0.0081 (7)	0.0072 (7)	0.0106 (8)
C00Z	0.0318 (9)	0.0336 (10)	0.0338 (10)	0.0124 (8)	0.0131 (8)	0.0132 (9)
C010	0.0316 (9)	0.0367 (10)	0.0380 (11)	0.0188 (8)	0.0077 (8)	0.0146 (9)
C011	0.0257 (9)	0.0409 (11)	0.0393 (11)	0.0111 (8)	0.0058 (8)	0.0198 (9)
C012	0.0286 (9)	0.0448 (11)	0.0326 (10)	0.0113 (8)	0.0035 (7)	0.0183 (9)
C013	0.0268 (9)	0.0314 (10)	0.0421 (11)	0.0112 (7)	0.0099 (8)	0.0152 (9)
C014	0.0308 (9)	0.0345 (10)	0.0311 (10)	0.0115 (8)	0.0025 (7)	0.0134 (9)
C015	0.0311 (9)	0.0413 (11)	0.0328 (10)	0.0159 (8)	0.0052 (8)	0.0152 (9)
C016	0.0413 (10)	0.0307 (10)	0.0331 (10)	0.0187 (8)	0.0099 (8)	0.0146 (8)
C017	0.0325 (10)	0.0540 (12)	0.0373 (11)	0.0237 (9)	0.0134 (8)	0.0223 (10)
C018	0.0347 (10)	0.0298 (10)	0.0356 (10)	0.0115 (8)	0.0103 (8)	0.0107 (9)
C019	0.0328 (9)	0.0385 (11)	0.0297 (10)	0.0115 (8)	0.0032 (8)	0.0136 (9)
C01A	0.0285 (9)	0.0421 (11)	0.0335 (10)	0.0123 (8)	0.0059 (7)	0.0178 (9)
C01B	0.0230 (9)	0.0580 (13)	0.0519 (12)	0.0130 (9)	0.0094 (8)	0.0359 (11)
C01C	0.0357 (10)	0.0353 (10)	0.0458 (12)	0.0142 (8)	0.0150 (9)	0.0220 (10)
C01D	0.0367 (10)	0.0424 (11)	0.0313 (10)	0.0057 (9)	0.0123 (8)	0.0107 (9)
C01E	0.0308 (10)	0.0394 (11)	0.0539 (13)	0.0086 (8)	0.0027 (9)	0.0272 (10)
C01F	0.0351 (10)	0.0629 (14)	0.0317 (10)	0.0271 (10)	0.0125 (8)	0.0229 (10)
C01G	0.0280 (9)	0.0490 (12)	0.0418 (11)	0.0187 (8)	0.0033 (8)	0.0197 (10)
C01H	0.0356 (10)	0.0550 (13)	0.0399 (11)	0.0269 (9)	0.0083 (9)	0.0228 (10)
C01I	0.0334 (10)	0.0525 (12)	0.0341 (11)	0.0012 (9)	0.0036 (8)	0.0260 (10)
C01J	0.0367 (11)	0.0376 (11)	0.0489 (12)	0.0097 (9)	0.0153 (9)	0.0144 (10)
C01K	0.0278 (9)	0.0423 (11)	0.0432 (12)	0.0152 (8)	0.0067 (8)	0.0109 (10)
C01L	0.0311 (10)	0.0485 (12)	0.0514 (13)	0.0094 (9)	0.0024 (9)	0.0316 (11)
C01M	0.0410 (11)	0.0339 (11)	0.0462 (12)	0.0147 (9)	−0.0071 (9)	0.0058 (10)
C01N	0.0352 (10)	0.0698 (15)	0.0411 (12)	0.0319 (10)	0.0160 (9)	0.0221 (11)
C01O	0.0472 (12)	0.0445 (12)	0.0462 (12)	0.0117 (9)	0.0110 (10)	0.0248 (11)
C01P	0.0352 (10)	0.0456 (12)	0.0421 (11)	0.0114 (9)	0.0014 (8)	0.0236 (10)
C01Q	0.0547 (13)	0.0431 (12)	0.0514 (13)	0.0306 (11)	0.0036 (11)	0.0126 (11)

Geometric parameters (Å, º)

Cl01—C016	1.7359 (17)	C00S—H00S	0.9300
Cl02—C01I	1.7370 (18)	C00S—C019	1.385 (2)
O003—C00Y	1.223 (2)	C00T—H00T	0.9300
O004—C00X	1.227 (2)	C00U—C00V	1.395 (3)
N005—H005	0.8600	C00U—C014	1.461 (2)
N005—N006	1.3794 (18)	C00V—H00V	0.9300
N005—C00X	1.357 (2)	C00V—C010	1.379 (2)
N006—C014	1.282 (2)	C00W—H00W	0.9300
N007—H007	0.8600	C00W—C00Z	1.385 (2)
N007—N00A	1.3865 (18)	C00W—C016	1.379 (2)
N007—C00Y	1.358 (2)	C00Z—H00Z	0.9300
N008—C00B	1.407 (2)	C010—H010	0.9300
N008—C00C	1.422 (2)	C011—H011	0.9300
N008—C00G	1.427 (2)	C011—C01L	1.384 (2)
N009—C00K	1.433 (2)	C012—H012	0.9300
N009—C00M	1.422 (2)	C012—C01H	1.370 (3)
N009—C00N	1.410 (2)	C013—H013	0.9300
N00A—C00O	1.277 (2)	C013—C01C	1.383 (2)
C00B—C00I	1.398 (2)	C014—H014	0.9300
C00B—C01A	1.393 (2)	C015—H015	0.9300
C00C—C00S	1.381 (2)	C015—C01K	1.385 (3)
C00C—C01F	1.386 (3)	C016—C01C	1.379 (3)
C00D—C00Y	1.495 (2)	C017—H017	0.9300
C00D—C011	1.387 (2)	C017—C01B	1.380 (3)
C00D—C018	1.393 (3)	C018—H018	0.9300
C00E—C00X	1.499 (2)	C018—C01D	1.388 (2)
C00E—C00Z	1.396 (2)	C019—H019	0.9300
C00E—C013	1.389 (2)	C019—C01G	1.375 (3)
C00F—C00J	1.393 (2)	C01A—H01A	0.9300
C00F—C00O	1.465 (2)	C01B—H01B	0.9300
C00F—C00T	1.395 (2)	C01B—C01E	1.370 (3)
C00G—C00P	1.386 (3)	C01C—H01C	0.9300
C00G—C00R	1.388 (3)	C01D—H01D	0.9300
C00H—H00H	0.9300	C01D—C01I	1.375 (3)
C00H—C00K	1.382 (3)	C01E—H01E	0.9300
C00H—C012	1.387 (2)	C01F—H01F	0.9300
C00I—H00I	0.9300	C01F—C01N	1.385 (3)
C00I—C00T	1.381 (2)	C01G—H01G	0.9300
C00J—H00J	0.9300	C01G—C01N	1.386 (3)
C00J—C01A	1.385 (2)	C01H—H01H	0.9300
C00K—C01M	1.381 (3)	C01H—C01Q	1.373 (3)
C00L—H00L	0.9300	C01I—C01L	1.381 (3)
C00L—C00Q	1.382 (2)	C01J—H01J	0.9300
C00L—C00U	1.394 (2)	C01J—C01K	1.376 (3)
C00M—C00Q	1.386 (3)	C01J—C01O	1.386 (3)
C00M—C010	1.396 (3)	C01K—H01K	0.9300
C00N—C015	1.392 (2)	C01L—H01L	0.9300
C00N—C01P	1.398 (2)	C01M—H01M	0.9300
C00O—H00O	0.9300	C01M—C01Q	1.383 (3)
C00P—H00P	0.9300	C01N—H01N	0.9300
C00P—C017	1.392 (2)	C01O—H01O	0.9300
C00Q—H00Q	0.9300	C01O—C01P	1.381 (3)
C00R—H00R	0.9300	C01P—H01P	0.9300
C00R—C01E	1.380 (3)	C01Q—H01Q	0.9300
N006—N005—H005	119.8	N007—C00Y—C00D	114.53 (15)
C00X—N005—H005	119.8	C00E—C00Z—H00Z	119.9
C00X—N005—N006	120.33 (15)	C00W—C00Z—C00E	120.29 (16)
C014—N006—N005	113.49 (15)	C00W—C00Z—H00Z	119.9
N00A—N007—H007	119.7	C00M—C010—H010	119.9
C00Y—N007—H007	119.7	C00V—C010—C00M	120.26 (17)
C00Y—N007—N00A	120.52 (15)	C00V—C010—H010	119.9
C00B—N008—C00C	121.64 (13)	C00D—C011—H011	119.7
C00B—N008—C00G	120.92 (13)	C01L—C011—C00D	120.53 (18)
C00C—N008—C00G	117.26 (13)	C01L—C011—H011	119.7
C00M—N009—C00K	116.74 (13)	C00H—C012—H012	119.7
C00N—N009—C00K	120.49 (13)	C01H—C012—C00H	120.64 (18)
C00N—N009—C00M	121.66 (14)	C01H—C012—H012	119.7
C00O—N00A—N007	113.89 (15)	C00E—C013—H013	119.7
C00I—C00B—N008	120.05 (15)	C01C—C013—C00E	120.69 (17)
C01A—C00B—N008	121.12 (15)	C01C—C013—H013	119.7
C01A—C00B—C00I	118.83 (15)	N006—C014—C00U	121.54 (17)
C00S—C00C—N008	119.72 (16)	N006—C014—H014	119.2
C00S—C00C—C01F	119.45 (16)	C00U—C014—H014	119.2
C01F—C00C—N008	120.80 (16)	C00N—C015—H015	119.7
C011—C00D—C00Y	116.74 (16)	C01K—C015—C00N	120.64 (17)
C011—C00D—C018	119.58 (15)	C01K—C015—H015	119.7
C018—C00D—C00Y	123.68 (16)	C00W—C016—Cl01	119.40 (14)
C00Z—C00E—C00X	123.42 (15)	C00W—C016—C01C	121.19 (16)
C013—C00E—C00X	117.39 (16)	C01C—C016—Cl01	119.41 (13)
C013—C00E—C00Z	119.11 (15)	C00P—C017—H017	119.9
C00J—C00F—C00O	119.51 (16)	C01B—C017—C00P	120.21 (18)
C00J—C00F—C00T	118.20 (15)	C01B—C017—H017	119.9
C00T—C00F—C00O	122.21 (16)	C00D—C018—H018	120.0
C00P—C00G—N008	120.61 (16)	C01D—C018—C00D	119.92 (17)
C00P—C00G—C00R	119.76 (16)	C01D—C018—H018	120.0
C00R—C00G—N008	119.56 (16)	C00S—C019—H019	119.9
C00K—C00H—H00H	120.2	C01G—C019—C00S	120.26 (17)
C00K—C00H—C012	119.67 (17)	C01G—C019—H019	119.9
C012—C00H—H00H	120.2	C00B—C01A—H01A	119.8
C00B—C00I—H00I	119.8	C00J—C01A—C00B	120.30 (16)
C00T—C00I—C00B	120.44 (16)	C00J—C01A—H01A	119.8
C00T—C00I—H00I	119.8	C017—C01B—H01B	120.0
C00F—C00J—H00J	119.4	C01E—C01B—C017	120.05 (17)
C01A—C00J—C00F	121.17 (16)	C01E—C01B—H01B	120.0
C01A—C00J—H00J	119.4	C013—C01C—H01C	120.4
C00H—C00K—N009	119.12 (16)	C016—C01C—C013	119.27 (16)
C01M—C00K—N009	121.51 (17)	C016—C01C—H01C	120.4
C01M—C00K—C00H	119.35 (16)	C018—C01D—H01D	120.3
C00Q—C00L—H00L	119.5	C01I—C01D—C018	119.43 (18)
C00Q—C00L—C00U	120.98 (17)	C01I—C01D—H01D	120.3
C00U—C00L—H00L	119.5	C00R—C01E—H01E	119.8
C00Q—C00M—N009	120.82 (16)	C01B—C01E—C00R	120.43 (18)
C00Q—C00M—C010	119.47 (15)	C01B—C01E—H01E	119.8
C010—C00M—N009	119.71 (16)	C00C—C01F—H01F	120.0
C015—C00N—N009	122.02 (15)	C01N—C01F—C00C	119.98 (17)
C015—C00N—C01P	118.04 (16)	C01N—C01F—H01F	120.0
C01P—C00N—N009	119.93 (16)	C019—C01G—H01G	120.2
N00A—C00O—C00F	121.94 (16)	C019—C01G—C01N	119.59 (17)
N00A—C00O—H00O	119.0	C01N—C01G—H01G	120.2
C00F—C00O—H00O	119.0	C012—C01H—H01H	120.1
C00G—C00P—H00P	120.2	C012—C01H—C01Q	119.85 (18)
C00G—C00P—C017	119.50 (17)	C01Q—C01H—H01H	120.1
C017—C00P—H00P	120.2	C01D—C01I—Cl02	119.60 (16)
C00L—C00Q—C00M	120.06 (17)	C01D—C01I—C01L	121.44 (16)
C00L—C00Q—H00Q	120.0	C01L—C01I—Cl02	118.96 (16)
C00M—C00Q—H00Q	120.0	C01K—C01J—H01J	120.6
C00G—C00R—H00R	120.0	C01K—C01J—C01O	118.85 (17)
C01E—C00R—C00G	120.04 (18)	C01O—C01J—H01J	120.6
C01E—C00R—H00R	120.0	C015—C01K—H01K	119.5
C00C—C00S—H00S	119.8	C01J—C01K—C015	121.01 (18)
C00C—C00S—C019	120.42 (17)	C01J—C01K—H01K	119.5
C019—C00S—H00S	119.8	C011—C01L—H01L	120.5
C00F—C00T—H00T	119.5	C01I—C01L—C011	119.05 (18)
C00I—C00T—C00F	121.05 (16)	C01I—C01L—H01L	120.5
C00I—C00T—H00T	119.5	C00K—C01M—H01M	119.7
C00L—C00U—C00V	118.55 (15)	C00K—C01M—C01Q	120.51 (19)
C00L—C00U—C014	118.76 (16)	C01Q—C01M—H01M	119.7
C00V—C00U—C014	122.68 (16)	C01F—C01N—C01G	120.30 (18)
C00U—C00V—H00V	119.7	C01F—C01N—H01N	119.9
C010—C00V—C00U	120.67 (17)	C01G—C01N—H01N	119.9
C010—C00V—H00V	119.7	C01J—C01O—H01O	119.7
C00Z—C00W—H00W	120.3	C01P—C01O—C01J	120.66 (18)
C016—C00W—H00W	120.3	C01P—C01O—H01O	119.7
C016—C00W—C00Z	119.44 (17)	C00N—C01P—H01P	119.6
O004—C00X—N005	123.43 (15)	C01O—C01P—C00N	120.76 (18)
O004—C00X—C00E	122.17 (15)	C01O—C01P—H01P	119.6
N005—C00X—C00E	114.40 (15)	C01H—C01Q—C01M	120.0 (2)
O003—C00Y—N007	123.78 (15)	C01H—C01Q—H01Q	120.0
O003—C00Y—C00D	121.68 (15)	C01M—C01Q—H01Q	120.0

(FormB)

Crystal data

C26H20ClN3O	F(000) = 1776
Mr = 425.90	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 15.6975 (7) Å	Cell parameters from 9055 reflections
b = 23.7324 (11) Å	θ = 2.9–66.6°
c = 12.0002 (4) Å	µ = 1.73 mm^−1
β = 102.451 (2)°	T = 170 K
V = 4365.4 (3) Å^3	Needle, colourless
Z = 8	0.2 × 0.05 × 0.02 mm

Data collection

Bruker APEX-II CCD diffractometer	5080 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.075
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1172 before and 0.0658 after correction. The Ratio of minimum to maximum transmission is 0.8611. The λ/2 correction factor is Not present.	θmax = 66.8°, θmin = 2.9°
Tmin = 0.648, Tmax = 0.753	h = −18→18
34810 measured reflections	k = −28→28
7724 independent reflections	l = −12→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 1.8383P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
7724 reflections	Δρmax = 0.25 e Å^−3
559 parameters	Δρmin = −0.29 e Å^−3
0 restraints

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
Cl01	−0.06221 (5)	0.76557 (4)	0.61531 (7)	0.0623 (2)
Cl02	0.10420 (5)	0.91271 (4)	1.10702 (8)	0.0713 (3)
O003	0.32173 (11)	0.88913 (7)	0.68873 (14)	0.0377 (4)
O004	0.23671 (11)	0.80388 (7)	0.30093 (15)	0.0417 (4)
N005	0.37012 (12)	0.86788 (8)	0.41517 (17)	0.0299 (5)
N006	0.29099 (12)	0.86307 (8)	0.44774 (17)	0.0311 (5)
H006	0.2811	0.8824	0.5063	0.037*
N007	0.37188 (12)	0.78212 (8)	0.65795 (16)	0.0303 (5)
N008	0.32305 (12)	0.79671 (8)	0.73691 (16)	0.0310 (5)
H008	0.3051	0.7705	0.7784	0.037*
N009	0.60231 (13)	0.64137 (7)	0.36790 (17)	0.0335 (5)
N00A	0.77758 (13)	0.91759 (9)	0.43710 (17)	0.0379 (5)
C00B	0.51506 (15)	0.90409 (9)	0.46508 (19)	0.0269 (5)
C00C	0.42632 (15)	0.89840 (9)	0.4821 (2)	0.0292 (5)
H00C	0.4099	0.9176	0.5437	0.035*
C00D	0.54806 (15)	0.86980 (9)	0.3894 (2)	0.0279 (5)
H00D	0.5109	0.8428	0.3448	0.033*
C00E	0.60681 (16)	0.58328 (9)	0.34102 (19)	0.0289 (5)
C00F	0.54933 (15)	0.66244 (9)	0.4386 (2)	0.0285 (5)
C00G	0.65462 (15)	0.68002 (9)	0.3193 (2)	0.0277 (5)
C00H	0.52125 (15)	0.71849 (9)	0.4278 (2)	0.0296 (5)
H00H	0.5367	0.7416	0.3706	0.036*
C00I	0.44635 (15)	0.70798 (9)	0.5826 (2)	0.0289 (5)
C00J	0.63306 (15)	0.87434 (9)	0.3785 (2)	0.0306 (6)
H00J	0.6541	0.8506	0.3267	0.037*
C00K	0.30313 (15)	0.85135 (10)	0.7499 (2)	0.0302 (5)
C00L	0.25585 (15)	0.86431 (10)	0.8426 (2)	0.0305 (5)
C00M	0.39404 (15)	0.73025 (10)	0.6593 (2)	0.0303 (5)
H00M	0.3759	0.7055	0.7118	0.036*
C00N	0.57104 (15)	0.94332 (10)	0.5296 (2)	0.0318 (6)
H00N	0.5503	0.9666	0.5824	0.038*
C00O	0.68890 (15)	0.91389 (10)	0.4433 (2)	0.0305 (5)
C00P	0.47156 (15)	0.74090 (10)	0.4986 (2)	0.0301 (5)
H00P	0.4542	0.7793	0.4902	0.036*
C00Q	0.22923 (16)	0.82853 (10)	0.3889 (2)	0.0315 (6)
C00R	0.68607 (17)	0.56085 (10)	0.3293 (2)	0.0341 (6)
H00R	0.7363	0.5842	0.3395	0.041*
C00S	0.80462 (16)	0.91069 (10)	0.3331 (2)	0.0325 (6)
C00T	0.15118 (15)	0.81932 (10)	0.4399 (2)	0.0323 (6)
C00U	0.65588 (15)	0.94876 (10)	0.5178 (2)	0.0322 (6)
H00U	0.6925	0.9765	0.5608	0.039*
C00V	0.24956 (16)	0.82766 (11)	0.9304 (2)	0.0362 (6)
H00V	0.2768	0.7918	0.9340	0.043*
C00W	0.88507 (16)	0.88657 (10)	0.3322 (2)	0.0359 (6)
H00W	0.9218	0.8746	0.4018	0.043*
C00X	0.53322 (17)	0.54911 (10)	0.3223 (2)	0.0348 (6)
H00X	0.4782	0.5644	0.3272	0.042*
C00Y	0.72267 (16)	0.70858 (10)	0.3883 (2)	0.0343 (6)
H00Y	0.7366	0.7018	0.4682	0.041*
C00Z	0.52423 (17)	0.62939 (10)	0.5221 (2)	0.0369 (6)
H00Z	0.5422	0.5911	0.5313	0.044*
C010	0.47329 (17)	0.65203 (10)	0.5917 (2)	0.0354 (6)
H010	0.4562	0.6287	0.6473	0.043*
C011	0.13407 (16)	0.84995 (11)	0.5314 (2)	0.0388 (6)
H011	0.1685	0.8821	0.5580	0.047*
C012	0.75168 (16)	0.75634 (10)	0.2247 (2)	0.0386 (6)
H012	0.7844	0.7830	0.1924	0.046*
C013	0.69172 (18)	0.50421 (10)	0.3025 (2)	0.0389 (6)
H013	0.7461	0.4889	0.2949	0.047*
C014	0.77055 (16)	0.74718 (11)	0.3406 (2)	0.0388 (6)
H014	0.8167	0.7674	0.3881	0.047*
C015	0.63597 (17)	0.68882 (10)	0.2026 (2)	0.0384 (6)
H015	0.5896	0.6689	0.1549	0.046*
C016	0.83905 (16)	0.93356 (12)	0.5374 (2)	0.0425 (7)
C017	0.20413 (17)	0.84248 (12)	1.0131 (2)	0.0430 (7)
H017	0.2003	0.8172	1.0732	0.052*
C018	0.91209 (18)	0.87987 (11)	0.2305 (2)	0.0440 (7)
H018	0.9676	0.8638	0.2308	0.053*
C019	0.54036 (19)	0.49254 (10)	0.2965 (2)	0.0415 (7)
H019	0.4903	0.4690	0.2855	0.050*
C01A	0.61947 (19)	0.47012 (10)	0.2868 (2)	0.0420 (7)
H01A	0.6239	0.4313	0.2693	0.050*
C01B	0.09654 (17)	0.77471 (11)	0.3983 (2)	0.0414 (6)
H01B	0.1051	0.7548	0.3329	0.050*
C01C	0.68532 (18)	0.72680 (11)	0.1558 (2)	0.0441 (7)
H01C	0.6733	0.7325	0.0755	0.053*
C01D	0.02972 (16)	0.75855 (11)	0.4502 (2)	0.0444 (7)
H01D	−0.0072	0.7278	0.4211	0.053*
C01E	0.01770 (17)	0.78785 (12)	0.5446 (2)	0.0430 (7)
C01F	0.06754 (16)	0.83420 (12)	0.5845 (2)	0.0445 (7)
H01F	0.0566	0.8551	0.6475	0.053*
C01G	0.75209 (17)	0.92756 (12)	0.2308 (2)	0.0440 (7)
H01G	0.6972	0.9445	0.2301	0.053*
C01H	0.16468 (17)	0.89452 (12)	1.0065 (2)	0.0439 (7)
C01I	0.21802 (18)	0.91722 (11)	0.8409 (2)	0.0463 (7)
H01I	0.2237	0.9434	0.7831	0.056*
C01J	0.77907 (19)	0.91990 (13)	0.1293 (2)	0.0524 (8)
H01J	0.7422	0.9310	0.0592	0.063*
C01K	0.84516 (19)	0.90293 (15)	0.6369 (3)	0.0598 (9)
H01K	0.8099	0.8705	0.6381	0.072*
C01L	0.17206 (19)	0.93232 (12)	0.9227 (3)	0.0524 (8)
H01L	0.1459	0.9685	0.9207	0.063*
C01M	0.8593 (2)	0.89622 (13)	0.1296 (3)	0.0527 (8)
H01M	0.8778	0.8913	0.0600	0.063*
C01N	0.8910 (2)	0.98025 (16)	0.5368 (3)	0.0789 (12)
H01N	0.8875	1.0015	0.4688	0.095*
C01O	0.9035 (3)	0.9202 (2)	0.7353 (3)	0.1028 (17)
H01O	0.9081	0.8996	0.8041	0.123*
C01P	0.9547 (3)	0.9671 (3)	0.7334 (5)	0.147 (3)
H01P	0.9943	0.9790	0.8007	0.177*
C01Q	0.9483 (3)	0.9958 (3)	0.6360 (5)	0.134 (3)
H01Q	0.9842	1.0279	0.6351	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0397 (4)	0.0902 (6)	0.0619 (5)	−0.0085 (4)	0.0220 (4)	0.0173 (4)
Cl02	0.0635 (5)	0.0885 (6)	0.0766 (6)	−0.0060 (4)	0.0481 (5)	−0.0309 (5)
O003	0.0473 (11)	0.0321 (9)	0.0384 (10)	−0.0014 (8)	0.0195 (8)	0.0008 (8)
O004	0.0469 (11)	0.0449 (11)	0.0385 (11)	−0.0031 (9)	0.0205 (9)	−0.0069 (9)
N005	0.0285 (11)	0.0311 (11)	0.0338 (12)	0.0033 (9)	0.0149 (9)	0.0068 (9)
N006	0.0275 (11)	0.0344 (11)	0.0355 (12)	0.0024 (9)	0.0161 (9)	−0.0015 (9)
N007	0.0341 (11)	0.0325 (11)	0.0280 (11)	0.0042 (9)	0.0151 (9)	−0.0004 (9)
N008	0.0368 (12)	0.0331 (11)	0.0277 (11)	0.0048 (9)	0.0169 (9)	0.0035 (9)
N009	0.0478 (13)	0.0197 (10)	0.0408 (12)	−0.0007 (9)	0.0267 (10)	−0.0025 (9)
N00A	0.0297 (11)	0.0546 (14)	0.0322 (12)	−0.0067 (10)	0.0131 (9)	−0.0054 (10)
C00B	0.0307 (13)	0.0267 (12)	0.0251 (12)	0.0041 (10)	0.0103 (10)	0.0063 (10)
C00C	0.0331 (13)	0.0283 (13)	0.0295 (13)	0.0047 (11)	0.0138 (11)	0.0050 (11)
C00D	0.0299 (13)	0.0250 (12)	0.0290 (13)	0.0008 (10)	0.0070 (10)	0.0038 (10)
C00E	0.0441 (15)	0.0217 (12)	0.0246 (13)	0.0009 (11)	0.0154 (11)	−0.0011 (10)
C00F	0.0349 (14)	0.0238 (12)	0.0295 (13)	−0.0006 (10)	0.0128 (11)	−0.0026 (10)
C00G	0.0355 (14)	0.0202 (12)	0.0314 (14)	0.0015 (10)	0.0161 (11)	−0.0007 (10)
C00H	0.0355 (14)	0.0264 (13)	0.0307 (13)	−0.0002 (10)	0.0153 (11)	0.0053 (10)
C00I	0.0317 (13)	0.0277 (13)	0.0292 (13)	−0.0003 (10)	0.0109 (11)	−0.0012 (10)
C00J	0.0354 (14)	0.0292 (13)	0.0307 (14)	0.0013 (11)	0.0150 (11)	−0.0013 (10)
C00K	0.0288 (13)	0.0336 (14)	0.0281 (13)	0.0003 (11)	0.0057 (10)	−0.0025 (11)
C00L	0.0266 (13)	0.0358 (14)	0.0303 (14)	0.0008 (11)	0.0087 (10)	−0.0058 (11)
C00M	0.0342 (14)	0.0311 (14)	0.0280 (13)	0.0003 (11)	0.0121 (11)	0.0027 (10)
C00N	0.0366 (14)	0.0322 (13)	0.0290 (13)	0.0048 (11)	0.0124 (11)	−0.0002 (10)
C00O	0.0275 (13)	0.0354 (14)	0.0301 (13)	0.0004 (11)	0.0099 (10)	0.0039 (11)
C00P	0.0354 (14)	0.0230 (12)	0.0349 (14)	0.0025 (10)	0.0141 (11)	0.0021 (10)
C00Q	0.0339 (14)	0.0316 (13)	0.0306 (14)	0.0044 (11)	0.0103 (11)	0.0039 (11)
C00R	0.0444 (15)	0.0305 (14)	0.0292 (14)	0.0027 (12)	0.0119 (11)	−0.0004 (10)
C00S	0.0357 (14)	0.0322 (14)	0.0331 (14)	−0.0067 (11)	0.0152 (11)	−0.0022 (11)
C00T	0.0292 (13)	0.0359 (14)	0.0334 (14)	0.0022 (11)	0.0102 (11)	0.0017 (11)
C00U	0.0337 (14)	0.0339 (14)	0.0296 (14)	−0.0013 (11)	0.0082 (11)	−0.0017 (11)
C00V	0.0396 (15)	0.0401 (15)	0.0319 (14)	0.0028 (12)	0.0143 (12)	−0.0034 (11)
C00W	0.0350 (14)	0.0356 (14)	0.0390 (15)	−0.0027 (12)	0.0125 (12)	−0.0018 (11)
C00X	0.0444 (16)	0.0293 (13)	0.0347 (14)	−0.0002 (12)	0.0174 (12)	−0.0013 (11)
C00Y	0.0400 (15)	0.0356 (14)	0.0290 (14)	0.0011 (12)	0.0114 (11)	−0.0046 (11)
C00Z	0.0557 (17)	0.0238 (13)	0.0369 (15)	0.0048 (12)	0.0229 (13)	0.0033 (11)
C010	0.0529 (16)	0.0275 (13)	0.0310 (14)	0.0000 (12)	0.0205 (12)	0.0047 (11)
C011	0.0317 (14)	0.0443 (16)	0.0427 (16)	−0.0018 (12)	0.0130 (12)	−0.0061 (12)
C012	0.0395 (15)	0.0327 (14)	0.0491 (17)	−0.0030 (12)	0.0215 (13)	0.0020 (12)
C013	0.0529 (17)	0.0339 (14)	0.0339 (15)	0.0114 (13)	0.0184 (13)	0.0033 (11)
C014	0.0322 (14)	0.0414 (15)	0.0436 (16)	−0.0061 (12)	0.0098 (12)	−0.0086 (12)
C015	0.0480 (16)	0.0352 (14)	0.0315 (14)	−0.0093 (12)	0.0076 (12)	0.0005 (11)
C016	0.0294 (14)	0.0573 (18)	0.0427 (17)	−0.0043 (13)	0.0120 (12)	−0.0188 (14)
C017	0.0463 (16)	0.0541 (18)	0.0324 (15)	−0.0054 (14)	0.0173 (13)	−0.0051 (13)
C018	0.0412 (16)	0.0422 (16)	0.0558 (19)	−0.0063 (13)	0.0266 (14)	−0.0111 (13)
C019	0.0604 (18)	0.0301 (14)	0.0402 (16)	−0.0094 (13)	0.0244 (14)	−0.0037 (12)
C01A	0.074 (2)	0.0224 (13)	0.0369 (16)	0.0036 (13)	0.0280 (14)	0.0004 (11)
C01B	0.0368 (15)	0.0446 (16)	0.0441 (16)	−0.0015 (13)	0.0111 (12)	−0.0053 (13)
C01C	0.0556 (18)	0.0434 (16)	0.0346 (15)	−0.0071 (14)	0.0126 (13)	0.0084 (12)
C01D	0.0311 (15)	0.0433 (16)	0.0591 (19)	−0.0046 (12)	0.0107 (13)	−0.0011 (14)
C01E	0.0288 (14)	0.0574 (18)	0.0452 (17)	0.0016 (13)	0.0130 (12)	0.0109 (14)
C01F	0.0319 (15)	0.0662 (19)	0.0383 (16)	−0.0010 (14)	0.0143 (12)	−0.0052 (14)
C01G	0.0380 (15)	0.0531 (17)	0.0441 (17)	0.0041 (13)	0.0159 (13)	0.0090 (13)
C01H	0.0331 (15)	0.0580 (18)	0.0463 (17)	−0.0040 (13)	0.0211 (13)	−0.0181 (14)
C01I	0.0576 (18)	0.0392 (16)	0.0472 (17)	0.0072 (14)	0.0224 (14)	−0.0015 (13)
C01J	0.0522 (18)	0.072 (2)	0.0351 (16)	−0.0060 (16)	0.0143 (14)	0.0110 (14)
C01K	0.0411 (17)	0.096 (3)	0.0410 (18)	0.0151 (17)	0.0067 (14)	−0.0101 (17)
C01L	0.0553 (19)	0.0467 (17)	0.061 (2)	0.0137 (14)	0.0253 (16)	−0.0120 (15)
C01M	0.0568 (19)	0.065 (2)	0.0437 (18)	−0.0157 (16)	0.0279 (15)	−0.0077 (15)
C01N	0.068 (2)	0.086 (3)	0.093 (3)	−0.038 (2)	0.041 (2)	−0.048 (2)
C01O	0.054 (2)	0.203 (5)	0.044 (2)	0.046 (3)	−0.0055 (19)	−0.030 (3)
C01P	0.038 (2)	0.287 (9)	0.110 (4)	0.006 (4)	0.001 (3)	−0.136 (5)
C01Q	0.071 (3)	0.183 (6)	0.161 (5)	−0.066 (3)	0.057 (4)	−0.135 (5)

Geometric parameters (Å, º)

Cl01—C01E	1.741 (3)	C00V—C017	1.386 (3)
Cl02—C01H	1.743 (2)	C00W—H00W	0.9500
O003—C00K	1.233 (3)	C00W—C018	1.385 (3)
O004—C00Q	1.234 (3)	C00X—H00X	0.9500
N005—N006	1.385 (2)	C00X—C019	1.387 (3)
N005—C00C	1.282 (3)	C00Y—H00Y	0.9500
N006—H006	0.8800	C00Y—C014	1.385 (3)
N006—C00Q	1.348 (3)	C00Z—H00Z	0.9500
N007—N008	1.385 (2)	C00Z—C010	1.383 (3)
N007—C00M	1.278 (3)	C010—H010	0.9500
N008—H008	0.8800	C011—H011	0.9500
N008—C00K	1.351 (3)	C011—C01F	1.387 (3)
N009—C00E	1.421 (3)	C012—H012	0.9500
N009—C00F	1.402 (3)	C012—C014	1.375 (4)
N009—C00G	1.436 (3)	C012—C01C	1.374 (4)
N00A—C00O	1.413 (3)	C013—H013	0.9500
N00A—C00S	1.412 (3)	C013—C01A	1.373 (4)
N00A—C016	1.423 (3)	C014—H014	0.9500
C00B—C00C	1.457 (3)	C015—H015	0.9500
C00B—C00D	1.399 (3)	C015—C01C	1.384 (3)
C00B—C00N	1.395 (3)	C016—C01K	1.384 (4)
C00C—H00C	0.9500	C016—C01N	1.377 (4)
C00D—H00D	0.9500	C017—H017	0.9500
C00D—C00J	1.373 (3)	C017—C01H	1.376 (4)
C00E—C00R	1.388 (3)	C018—H018	0.9500
C00E—C00X	1.389 (3)	C018—C01M	1.368 (4)
C00F—C00H	1.399 (3)	C019—H019	0.9500
C00F—C00Z	1.395 (3)	C019—C01A	1.379 (4)
C00G—C00Y	1.380 (3)	C01A—H01A	0.9500
C00G—C015	1.384 (3)	C01B—H01B	0.9500
C00H—H00H	0.9500	C01B—C01D	1.384 (3)
C00H—C00P	1.377 (3)	C01C—H01C	0.9500
C00I—C00M	1.458 (3)	C01D—H01D	0.9500
C00I—C00P	1.399 (3)	C01D—C01E	1.377 (4)
C00I—C010	1.391 (3)	C01E—C01F	1.375 (4)
C00J—H00J	0.9500	C01F—H01F	0.9500
C00J—C00O	1.400 (3)	C01G—H01G	0.9500
C00K—C00L	1.496 (3)	C01G—C01J	1.385 (4)
C00L—C00V	1.387 (3)	C01H—C01L	1.371 (4)
C00L—C01I	1.387 (3)	C01I—H01I	0.9500
C00M—H00M	0.9500	C01I—C01L	1.384 (4)
C00N—H00N	0.9500	C01J—H01J	0.9500
C00N—C00U	1.375 (3)	C01J—C01M	1.378 (4)
C00O—C00U	1.397 (3)	C01K—H01K	0.9500
C00P—H00P	0.9500	C01K—C01O	1.391 (5)
C00Q—C00T	1.499 (3)	C01L—H01L	0.9500
C00R—H00R	0.9500	C01M—H01M	0.9500
C00R—C013	1.389 (3)	C01N—H01N	0.9500
C00S—C00W	1.389 (3)	C01N—C01Q	1.378 (6)
C00S—C01G	1.382 (4)	C01O—H01O	0.9500
C00T—C011	1.391 (3)	C01O—C01P	1.375 (8)
C00T—C01B	1.386 (3)	C01P—H01P	0.9500
C00U—H00U	0.9500	C01P—C01Q	1.338 (9)
C00V—H00V	0.9500	C01Q—H01Q	0.9500
C00C—N005—N006	114.06 (19)	C014—C00Y—H00Y	120.1
N005—N006—H006	120.3	C00F—C00Z—H00Z	119.8
C00Q—N006—N005	119.33 (19)	C010—C00Z—C00F	120.3 (2)
C00Q—N006—H006	120.3	C010—C00Z—H00Z	119.8
C00M—N007—N008	114.93 (19)	C00I—C010—H010	119.0
N007—N008—H008	120.2	C00Z—C010—C00I	122.0 (2)
C00K—N008—N007	119.67 (19)	C00Z—C010—H010	119.0
C00K—N008—H008	120.2	C00T—C011—H011	119.5
C00E—N009—C00G	117.83 (17)	C01F—C011—C00T	121.0 (2)
C00F—N009—C00E	123.25 (18)	C01F—C011—H011	119.5
C00F—N009—C00G	118.92 (17)	C014—C012—H012	120.1
C00O—N00A—C016	117.92 (19)	C01C—C012—H012	120.1
C00S—N00A—C00O	121.8 (2)	C01C—C012—C014	119.9 (2)
C00S—N00A—C016	120.1 (2)	C00R—C013—H013	119.7
C00D—C00B—C00C	122.4 (2)	C01A—C013—C00R	120.7 (2)
C00N—C00B—C00C	119.4 (2)	C01A—C013—H013	119.7
C00N—C00B—C00D	118.1 (2)	C00Y—C014—H014	119.8
N005—C00C—C00B	120.9 (2)	C012—C014—C00Y	120.3 (2)
N005—C00C—H00C	119.5	C012—C014—H014	119.8
C00B—C00C—H00C	119.5	C00G—C015—H015	120.2
C00B—C00D—H00D	119.3	C00G—C015—C01C	119.6 (2)
C00J—C00D—C00B	121.3 (2)	C01C—C015—H015	120.2
C00J—C00D—H00D	119.3	C01K—C016—N00A	119.9 (3)
C00R—C00E—N009	119.0 (2)	C01N—C016—N00A	120.3 (3)
C00R—C00E—C00X	119.5 (2)	C01N—C016—C01K	119.8 (3)
C00X—C00E—N009	121.5 (2)	C00V—C017—H017	120.6
C00H—C00F—N009	120.0 (2)	C01H—C017—C00V	118.7 (3)
C00Z—C00F—N009	122.0 (2)	C01H—C017—H017	120.6
C00Z—C00F—C00H	118.0 (2)	C00W—C018—H018	119.8
C00Y—C00G—N009	120.4 (2)	C01M—C018—C00W	120.3 (3)
C00Y—C00G—C015	120.0 (2)	C01M—C018—H018	119.8
C015—C00G—N009	119.5 (2)	C00X—C019—H019	119.7
C00F—C00H—H00H	119.4	C01A—C019—C00X	120.6 (2)
C00P—C00H—C00F	121.3 (2)	C01A—C019—H019	119.7
C00P—C00H—H00H	119.4	C013—C01A—C019	119.6 (2)
C00P—C00I—C00M	122.5 (2)	C013—C01A—H01A	120.2
C010—C00I—C00M	120.0 (2)	C019—C01A—H01A	120.2
C010—C00I—C00P	117.5 (2)	C00T—C01B—H01B	119.3
C00D—C00J—H00J	119.9	C01D—C01B—C00T	121.3 (3)
C00D—C00J—C00O	120.3 (2)	C01D—C01B—H01B	119.3
C00O—C00J—H00J	119.9	C012—C01C—C015	120.4 (2)
O003—C00K—N008	122.6 (2)	C012—C01C—H01C	119.8
O003—C00K—C00L	120.8 (2)	C015—C01C—H01C	119.8
N008—C00K—C00L	116.6 (2)	C01B—C01D—H01D	120.6
C00V—C00L—C00K	124.3 (2)	C01E—C01D—C01B	118.8 (3)
C00V—C00L—C01I	118.6 (2)	C01E—C01D—H01D	120.6
C01I—C00L—C00K	117.0 (2)	C01D—C01E—Cl01	119.3 (2)
N007—C00M—C00I	122.0 (2)	C01F—C01E—Cl01	119.3 (2)
N007—C00M—H00M	119.0	C01F—C01E—C01D	121.5 (2)
C00I—C00M—H00M	119.0	C011—C01F—H01F	120.5
C00B—C00N—H00N	119.5	C01E—C01F—C011	119.0 (3)
C00U—C00N—C00B	120.9 (2)	C01E—C01F—H01F	120.5
C00U—C00N—H00N	119.5	C00S—C01G—H01G	119.8
C00J—C00O—N00A	121.2 (2)	C00S—C01G—C01J	120.4 (3)
C00U—C00O—N00A	120.2 (2)	C01J—C01G—H01G	119.8
C00U—C00O—C00J	118.6 (2)	C017—C01H—Cl02	119.2 (2)
C00H—C00P—C00I	121.0 (2)	C01L—C01H—Cl02	119.4 (2)
C00H—C00P—H00P	119.5	C01L—C01H—C017	121.5 (2)
C00I—C00P—H00P	119.5	C00L—C01I—H01I	119.6
O004—C00Q—N006	123.1 (2)	C01L—C01I—C00L	120.7 (3)
O004—C00Q—C00T	121.1 (2)	C01L—C01I—H01I	119.6
N006—C00Q—C00T	115.7 (2)	C01G—C01J—H01J	119.9
C00E—C00R—H00R	120.1	C01M—C01J—C01G	120.2 (3)
C00E—C00R—C013	119.9 (2)	C01M—C01J—H01J	119.9
C013—C00R—H00R	120.1	C016—C01K—H01K	120.4
C00W—C00S—N00A	120.1 (2)	C016—C01K—C01O	119.2 (4)
C01G—C00S—N00A	121.1 (2)	C01O—C01K—H01K	120.4
C01G—C00S—C00W	118.8 (2)	C01H—C01L—C01I	119.3 (3)
C011—C00T—C00Q	124.1 (2)	C01H—C01L—H01L	120.3
C01B—C00T—C00Q	117.5 (2)	C01I—C01L—H01L	120.3
C01B—C00T—C011	118.3 (2)	C018—C01M—C01J	119.8 (3)
C00N—C00U—C00O	120.7 (2)	C018—C01M—H01M	120.1
C00N—C00U—H00U	119.6	C01J—C01M—H01M	120.1
C00O—C00U—H00U	119.6	C016—C01N—H01N	120.4
C00L—C00V—H00V	119.4	C016—C01N—C01Q	119.2 (4)
C00L—C00V—C017	121.1 (2)	C01Q—C01N—H01N	120.4
C017—C00V—H00V	119.4	C01K—C01O—H01O	119.8
C00S—C00W—H00W	119.8	C01P—C01O—C01K	120.4 (5)
C018—C00W—C00S	120.4 (3)	C01P—C01O—H01O	119.8
C018—C00W—H00W	119.8	C01O—C01P—H01P	120.3
C00E—C00X—H00X	120.1	C01Q—C01P—C01O	119.5 (4)
C019—C00X—C00E	119.8 (2)	C01Q—C01P—H01P	120.3
C019—C00X—H00X	120.1	C01N—C01Q—H01Q	119.0
C00G—C00Y—H00Y	120.1	C01P—C01Q—C01N	122.0 (5)
C00G—C00Y—C014	119.7 (2)	C01P—C01Q—H01Q	119.0