Crystal structure of imidazo[1,5-a]pyridinium-based hybrid salt (C₁₃H₁₂N₃)₂[MnCl₄]

The replacement of Zn^II with Mn^II ions in the hybrid structure, which also changed the space group from ortho­rhom­bic Pbca with Z = 8 to monoclinic P2₁/c with Z = 4, quenched the fluorescence emission of the hybrid material.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.186
• Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         14 Note

Author Response: These reflections were hidden behind the beam stop mask. Default parameters were used for the mask.

Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.631 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          4 Check

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Mn1       (II)      .       2.11 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law         [ 1 0 4] Est.d BASF       0.16 Check

Author Response: Twin Law (-1 0 0 0 -1 0 0.5 0 1) was applied in the refinement where the twin component fraction refined to 0.155(1).

PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   3 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.
PUBL022_ALERT_1_A There is a mismatched ~ on line 308
              signals at approximately 900, 2200, 5000 and 6000 G (77 K; <i>g</i>~eff~ \~
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 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: CrysAlis PRO (Rigaku OD, 2016); cell refinement: CrysAlis PRO (Rigaku OD, 2016); data reduction: CrysAlis PRO (Rigaku OD, 2016); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium] tetrachloridomanganate(II)

Crystal data

(C13H12N3)2[MnCl4]	F(000) = 1260
Mr = 617.25	Dx = 1.536 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10548 reflections
a = 7.4892 (1) Å	θ = 3.6–34.6°
b = 15.9488 (4) Å	µ = 0.92 mm^−1
c = 22.4266 (5) Å	T = 100 K
β = 94.896 (2)°	Needle, colourless
V = 2668.94 (10) Å^3	0.36 × 0.1 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Gemini diffractometer	7856 independent reflections
Graphite monochromator	6781 reflections with I > 2σ(I)
Detector resolution: 10.4738 pixels mm^-1	Rint = 0.069
ω scans	θmax = 30.1°, θmin = 3.6°
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2016)	h = −10→10
Tmin = 0.753, Tmax = 0.942	k = −22→22
7856 measured reflections	l = −4→31

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.186	w = 1/[σ^2(Fo^2) + (0.106P)^2 + 2.4383P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
7856 reflections	Δρmax = 0.58 e Å^−3
337 parameters	Δρmin = −0.69 e Å^−3

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.

Refinement. Refined as a 2-component twin using PLATON to de-twin the data.

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

	x	y	z	Uiso*/Ueq
Mn1	0.18155 (7)	0.24718 (3)	0.12270 (2)	0.01416 (13)
Cl1	−0.09406 (11)	0.17752 (5)	0.10546 (4)	0.01936 (17)
Cl2	0.41361 (11)	0.14691 (5)	0.12578 (3)	0.01805 (17)
Cl3	0.18969 (12)	0.31455 (5)	0.21748 (3)	0.01903 (17)
Cl4	0.22558 (12)	0.35257 (5)	0.04936 (4)	0.02042 (18)
C11	0.7917 (5)	0.1463 (2)	0.25204 (15)	0.0163 (6)
H11	0.743093	0.121304	0.215771	0.02*
N12	0.7856 (4)	0.22928 (17)	0.26666 (12)	0.0149 (5)
C12	0.6912 (5)	0.2909 (2)	0.22796 (16)	0.0207 (7)
H12A	0.619181	0.327043	0.251868	0.031*
H12B	0.612553	0.262038	0.197364	0.031*
H12C	0.778253	0.32509	0.208559	0.031*
C13	0.8700 (4)	0.2431 (2)	0.32148 (14)	0.0143 (6)
N13A	0.9302 (4)	0.16698 (17)	0.34265 (12)	0.0139 (5)
C14	1.0262 (5)	0.1464 (2)	0.39668 (15)	0.0171 (6)
H14	1.05983	0.188652	0.425342	0.02*
C15	1.0708 (5)	0.0651 (2)	0.40762 (15)	0.0197 (6)
H15	1.137344	0.050607	0.444133	0.024*
C16	1.0194 (5)	0.0007 (2)	0.36519 (16)	0.0211 (7)
H16	1.04999	−0.056041	0.374005	0.025*
C17	0.9270 (5)	0.0205 (2)	0.31227 (16)	0.0191 (6)
H17	0.893137	−0.022108	0.283952	0.023*
C17A	0.8815 (4)	0.1056 (2)	0.29965 (14)	0.0150 (6)
C21	0.6189 (4)	0.0675 (2)	0.43736 (16)	0.0182 (6)
H21	0.676985	0.022658	0.459085	0.022*
N22	0.6065 (4)	0.14828 (18)	0.45664 (12)	0.0161 (5)
C22	0.6955 (5)	0.1792 (2)	0.51343 (15)	0.0216 (7)
H22A	0.734725	0.237161	0.508343	0.032*
H22B	0.79976	0.143911	0.525234	0.032*
H22C	0.61138	0.17701	0.544551	0.032*
C23	0.5132 (4)	0.1952 (2)	0.41441 (14)	0.0153 (6)
N23A	0.4677 (4)	0.14328 (17)	0.36724 (12)	0.0148 (5)
C24	0.3675 (4)	0.1610 (2)	0.31331 (14)	0.0170 (6)
H24	0.320143	0.215412	0.305083	0.02*
C25	0.3403 (5)	0.0979 (2)	0.27312 (16)	0.0205 (7)
H25	0.274347	0.108817	0.23585	0.025*
C26	0.4079 (5)	0.0154 (2)	0.28524 (16)	0.0210 (7)
H26	0.38685	−0.0273	0.255977	0.025*
C27	0.5020 (5)	−0.0026 (2)	0.33805 (16)	0.0199 (6)
H27	0.546507	−0.05758	0.34619	0.024*
C27A	0.5324 (4)	0.0626 (2)	0.38099 (15)	0.0155 (6)
C131	0.8898 (4)	0.3228 (2)	0.35385 (14)	0.0147 (6)
C136	0.9174 (5)	0.3981 (2)	0.32441 (14)	0.0164 (6)
H136	0.930694	0.398767	0.28266	0.02*
C135	0.9251 (5)	0.4717 (2)	0.35712 (16)	0.0201 (7)
H135	0.941632	0.524	0.338116	0.024*
C134	0.9082 (5)	0.4677 (2)	0.41862 (16)	0.0200 (7)
H134	0.911474	0.51718	0.442251	0.024*
C133	0.8864 (5)	0.3896 (2)	0.44431 (14)	0.0187 (6)
H133	0.87798	0.386788	0.486295	0.022*
N132	0.8764 (4)	0.31762 (18)	0.41298 (13)	0.0180 (5)
C231	0.4668 (4)	0.2846 (2)	0.41729 (14)	0.0143 (6)
C236	0.4232 (5)	0.3215 (2)	0.47027 (15)	0.0185 (6)
H236	0.421074	0.289572	0.505961	0.022*
C235	0.3827 (5)	0.4069 (2)	0.46946 (16)	0.0219 (7)
H235	0.35516	0.434543	0.505041	0.026*
C234	0.3830 (5)	0.4504 (2)	0.41675 (17)	0.0234 (7)
H234	0.355126	0.508481	0.415031	0.028*
C233	0.4251 (5)	0.4074 (2)	0.36591 (17)	0.0219 (7)
H233	0.423424	0.437845	0.329457	0.026*
N232	0.4674 (4)	0.32664 (18)	0.36493 (13)	0.0173 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0153 (2)	0.0128 (2)	0.0146 (2)	0.00108 (18)	0.00254 (17)	0.00018 (17)
Cl1	0.0168 (4)	0.0201 (4)	0.0213 (4)	−0.0013 (3)	0.0021 (3)	0.0024 (3)
Cl2	0.0175 (3)	0.0190 (4)	0.0177 (3)	0.0041 (3)	0.0019 (3)	−0.0019 (3)
Cl3	0.0244 (4)	0.0162 (3)	0.0166 (3)	0.0054 (3)	0.0023 (3)	−0.0013 (3)
Cl4	0.0271 (4)	0.0148 (3)	0.0200 (4)	0.0001 (3)	0.0054 (3)	0.0025 (3)
C11	0.0196 (15)	0.0131 (13)	0.0165 (14)	−0.0046 (12)	0.0028 (12)	−0.0042 (11)
N12	0.0161 (13)	0.0110 (11)	0.0176 (12)	−0.0003 (10)	0.0018 (10)	−0.0003 (9)
C12	0.0257 (17)	0.0140 (14)	0.0216 (15)	0.0030 (13)	−0.0032 (13)	0.0016 (12)
C13	0.0131 (13)	0.0138 (14)	0.0163 (14)	−0.0017 (11)	0.0044 (11)	−0.0008 (11)
N13A	0.0145 (12)	0.0124 (11)	0.0152 (12)	−0.0005 (10)	0.0041 (10)	−0.0004 (9)
C14	0.0158 (14)	0.0172 (15)	0.0181 (14)	0.0005 (12)	0.0004 (11)	0.0000 (12)
C15	0.0204 (16)	0.0178 (15)	0.0212 (15)	0.0031 (13)	0.0043 (12)	0.0043 (12)
C16	0.0199 (16)	0.0172 (15)	0.0277 (17)	0.0015 (13)	0.0104 (13)	0.0039 (13)
C17	0.0195 (16)	0.0125 (14)	0.0260 (16)	−0.0007 (12)	0.0068 (13)	−0.0016 (12)
C17A	0.0147 (14)	0.0135 (14)	0.0172 (14)	−0.0015 (11)	0.0035 (11)	−0.0030 (11)
C21	0.0143 (14)	0.0134 (14)	0.0266 (16)	0.0024 (12)	0.0006 (12)	0.0037 (12)
N22	0.0155 (12)	0.0166 (12)	0.0164 (12)	0.0005 (11)	0.0022 (10)	0.0013 (10)
C22	0.0224 (17)	0.0240 (17)	0.0174 (15)	−0.0004 (14)	−0.0037 (13)	0.0019 (13)
C23	0.0151 (14)	0.0169 (14)	0.0144 (13)	−0.0005 (12)	0.0044 (11)	−0.0005 (11)
N23A	0.0132 (12)	0.0130 (12)	0.0182 (12)	−0.0010 (10)	0.0011 (10)	−0.0003 (10)
C24	0.0158 (14)	0.0199 (15)	0.0155 (14)	−0.0026 (12)	0.0030 (11)	−0.0002 (12)
C25	0.0198 (16)	0.0217 (16)	0.0201 (15)	−0.0083 (14)	0.0026 (12)	−0.0015 (13)
C26	0.0217 (16)	0.0188 (15)	0.0235 (16)	−0.0056 (13)	0.0072 (13)	−0.0062 (13)
C27	0.0191 (16)	0.0128 (14)	0.0286 (17)	−0.0009 (12)	0.0057 (13)	−0.0008 (12)
C27A	0.0125 (13)	0.0133 (13)	0.0205 (15)	−0.0002 (11)	0.0007 (11)	−0.0003 (11)
C131	0.0129 (13)	0.0123 (13)	0.0187 (14)	−0.0019 (11)	0.0002 (11)	−0.0015 (11)
C136	0.0181 (15)	0.0146 (14)	0.0168 (14)	−0.0008 (12)	0.0029 (12)	−0.0005 (11)
C135	0.0208 (16)	0.0130 (14)	0.0265 (17)	0.0005 (13)	0.0018 (13)	0.0004 (12)
C134	0.0217 (16)	0.0117 (14)	0.0264 (17)	0.0010 (12)	0.0020 (13)	−0.0057 (12)
C133	0.0205 (16)	0.0227 (16)	0.0132 (13)	−0.0019 (13)	0.0025 (12)	−0.0026 (12)
N132	0.0182 (13)	0.0152 (13)	0.0212 (13)	−0.0017 (11)	0.0052 (11)	−0.0015 (10)
C231	0.0140 (14)	0.0127 (13)	0.0163 (14)	−0.0013 (11)	0.0016 (11)	−0.0002 (11)
C236	0.0203 (16)	0.0177 (15)	0.0186 (15)	−0.0012 (13)	0.0074 (12)	0.0013 (12)
C235	0.0255 (17)	0.0157 (15)	0.0258 (17)	−0.0015 (14)	0.0096 (14)	−0.0053 (13)
C234	0.0253 (17)	0.0121 (14)	0.0338 (19)	−0.0001 (13)	0.0085 (15)	−0.0013 (13)
C233	0.0226 (16)	0.0165 (15)	0.0266 (17)	0.0020 (13)	0.0024 (13)	0.0036 (13)
N232	0.0164 (13)	0.0148 (12)	0.0207 (13)	−0.0007 (11)	0.0015 (10)	0.0010 (10)

Geometric parameters (Å, º)

Mn1—Cl1	2.3469 (10)	C23—N23A	1.364 (4)
Mn1—Cl2	2.3585 (9)	C23—C231	1.471 (5)
Mn1—Cl3	2.3779 (9)	N23A—C24	1.396 (4)
Mn1—Cl4	2.3941 (9)	N23A—C27A	1.400 (4)
C11—N12	1.366 (4)	C24—C25	1.355 (5)
C11—C17A	1.375 (5)	C24—H24	0.95
C11—H11	0.95	C25—C26	1.427 (5)
N12—C13	1.352 (4)	C25—H25	0.95
N12—C12	1.454 (4)	C26—C27	1.356 (5)
C12—H12A	0.98	C26—H26	0.95
C12—H12B	0.98	C27—C27A	1.423 (5)
C12—H12C	0.98	C27—H27	0.95
C13—N13A	1.367 (4)	C131—N132	1.341 (4)
C13—C131	1.465 (4)	C131—C136	1.394 (4)
N13A—C14	1.394 (4)	C136—C135	1.383 (5)
N13A—C17A	1.400 (4)	C136—H136	0.95
C14—C15	1.357 (5)	C135—C134	1.397 (5)
C14—H14	0.95	C135—H135	0.95
C15—C16	1.430 (5)	C134—C133	1.388 (5)
C15—H15	0.95	C134—H134	0.95
C16—C17	1.359 (5)	C133—N132	1.344 (4)
C16—H16	0.95	C133—H133	0.95
C17—C17A	1.422 (4)	C231—N232	1.353 (4)
C17—H17	0.95	C231—C236	1.390 (4)
C21—N22	1.364 (4)	C236—C235	1.394 (5)
C21—C27A	1.373 (5)	C236—H236	0.95
C21—H21	0.95	C235—C234	1.371 (5)
N22—C23	1.353 (4)	C235—H235	0.95
N22—C22	1.471 (4)	C234—C233	1.389 (5)
C22—H22A	0.98	C234—H234	0.95
C22—H22B	0.98	C233—N232	1.327 (4)
C22—H22C	0.98	C233—H233	0.95
Cl1—Mn1—Cl2	108.62 (3)	N22—C23—C231	128.0 (3)
Cl1—Mn1—Cl3	108.44 (3)	N23A—C23—C231	125.3 (3)
Cl2—Mn1—Cl3	108.51 (3)	C23—N23A—C24	129.0 (3)
Cl1—Mn1—Cl4	112.95 (4)	C23—N23A—C27A	109.2 (3)
Cl2—Mn1—Cl4	110.60 (3)	C24—N23A—C27A	121.8 (3)
Cl3—Mn1—Cl4	107.60 (3)	C25—C24—N23A	117.7 (3)
N12—C11—C17A	107.2 (3)	C25—C24—H24	121.1
N12—C11—H11	126.4	N23A—C24—H24	121.1
C17A—C11—H11	126.4	C24—C25—C26	121.8 (3)
C13—N12—C11	110.7 (3)	C24—C25—H25	119.1
C13—N12—C12	126.7 (3)	C26—C25—H25	119.1
C11—N12—C12	122.4 (3)	C27—C26—C25	120.8 (3)
N12—C12—H12A	109.5	C27—C26—H26	119.6
N12—C12—H12B	109.5	C25—C26—H26	119.6
H12A—C12—H12B	109.5	C26—C27—C27A	118.5 (3)
N12—C12—H12C	109.5	C26—C27—H27	120.8
H12A—C12—H12C	109.5	C27A—C27—H27	120.8
H12B—C12—H12C	109.5	C21—C27A—N23A	106.1 (3)
N12—C13—N13A	106.6 (3)	C21—C27A—C27	134.5 (3)
N12—C13—C131	127.8 (3)	N23A—C27A—C27	119.4 (3)
N13A—C13—C131	125.6 (3)	N132—C131—C136	123.3 (3)
C13—N13A—C14	129.9 (3)	N132—C131—C13	115.1 (3)
C13—N13A—C17A	108.9 (3)	C136—C131—C13	121.7 (3)
C14—N13A—C17A	121.2 (3)	C135—C136—C131	118.7 (3)
C15—C14—N13A	118.9 (3)	C135—C136—H136	120.6
C15—C14—H14	120.6	C131—C136—H136	120.6
N13A—C14—H14	120.6	C136—C135—C134	118.8 (3)
C14—C15—C16	121.2 (3)	C136—C135—H135	120.6
C14—C15—H15	119.4	C134—C135—H135	120.6
C16—C15—H15	119.4	C133—C134—C135	118.3 (3)
C17—C16—C15	120.1 (3)	C133—C134—H134	120.8
C17—C16—H16	119.9	C135—C134—H134	120.8
C15—C16—H16	119.9	N132—C133—C134	123.5 (3)
C16—C17—C17A	119.4 (3)	N132—C133—H133	118.2
C16—C17—H17	120.3	C134—C133—H133	118.2
C17A—C17—H17	120.3	C131—N132—C133	117.3 (3)
C11—C17A—N13A	106.6 (3)	N232—C231—C236	123.4 (3)
C11—C17A—C17	134.3 (3)	N232—C231—C23	115.1 (3)
N13A—C17A—C17	119.1 (3)	C236—C231—C23	121.5 (3)
N22—C21—C27A	107.8 (3)	C231—C236—C235	118.0 (3)
N22—C21—H21	126.1	C231—C236—H236	121
C27A—C21—H21	126.1	C235—C236—H236	121
C23—N22—C21	110.2 (3)	C234—C235—C236	119.3 (3)
C23—N22—C22	126.1 (3)	C234—C235—H235	120.4
C21—N22—C22	123.5 (3)	C236—C235—H235	120.4
N22—C22—H22A	109.5	C235—C234—C233	118.4 (3)
N22—C22—H22B	109.5	C235—C234—H234	120.8
H22A—C22—H22B	109.5	C233—C234—H234	120.8
N22—C22—H22C	109.5	N232—C233—C234	124.3 (3)
H22A—C22—H22C	109.5	N232—C233—H233	117.8
H22B—C22—H22C	109.5	C234—C233—H233	117.8
N22—C23—N23A	106.7 (3)	C233—N232—C231	116.6 (3)
C17A—C11—N12—C13	0.7 (4)	N23A—C24—C25—C26	1.1 (5)
C17A—C11—N12—C12	−176.4 (3)	C24—C25—C26—C27	0.3 (5)
C11—N12—C13—N13A	−0.5 (4)	C25—C26—C27—C27A	−0.3 (5)
C12—N12—C13—N13A	176.5 (3)	N22—C21—C27A—N23A	0.0 (4)
C11—N12—C13—C131	−178.6 (3)	N22—C21—C27A—C27	178.9 (4)
C12—N12—C13—C131	−1.6 (5)	C23—N23A—C27A—C21	−0.4 (4)
N12—C13—N13A—C14	179.6 (3)	C24—N23A—C27A—C21	−178.2 (3)
C131—C13—N13A—C14	−2.3 (5)	C23—N23A—C27A—C27	−179.6 (3)
N12—C13—N13A—C17A	0.1 (4)	C24—N23A—C27A—C27	2.6 (5)
C131—C13—N13A—C17A	178.2 (3)	C26—C27—C27A—C21	−180.0 (4)
C13—N13A—C14—C15	179.8 (3)	C26—C27—C27A—N23A	−1.1 (5)
C17A—N13A—C14—C15	−0.8 (5)	N12—C13—C131—N132	141.6 (3)
N13A—C14—C15—C16	−0.7 (5)	N13A—C13—C131—N132	−36.1 (5)
C14—C15—C16—C17	1.2 (5)	N12—C13—C131—C136	−37.3 (5)
C15—C16—C17—C17A	−0.2 (5)	N13A—C13—C131—C136	144.9 (3)
N12—C11—C17A—N13A	−0.7 (4)	N132—C131—C136—C135	−2.4 (5)
N12—C11—C17A—C17	178.3 (4)	C13—C131—C136—C135	176.5 (3)
C13—N13A—C17A—C11	0.4 (4)	C131—C136—C135—C134	1.1 (5)
C14—N13A—C17A—C11	−179.2 (3)	C136—C135—C134—C133	0.7 (5)
C13—N13A—C17A—C17	−178.8 (3)	C135—C134—C133—N132	−1.6 (5)
C14—N13A—C17A—C17	1.7 (5)	C136—C131—N132—C133	1.6 (5)
C16—C17—C17A—C11	180.0 (4)	C13—C131—N132—C133	−177.3 (3)
C16—C17—C17A—N13A	−1.2 (5)	C134—C133—N132—C131	0.4 (5)
C27A—C21—N22—C23	0.5 (4)	N22—C23—C231—N232	144.4 (3)
C27A—C21—N22—C22	−175.1 (3)	N23A—C23—C231—N232	−35.8 (5)
C21—N22—C23—N23A	−0.7 (4)	N22—C23—C231—C236	−36.6 (5)
C22—N22—C23—N23A	174.7 (3)	N23A—C23—C231—C236	143.2 (3)
C21—N22—C23—C231	179.0 (3)	N232—C231—C236—C235	−1.8 (5)
C22—N22—C23—C231	−5.5 (5)	C23—C231—C236—C235	179.3 (3)
N22—C23—N23A—C24	178.3 (3)	C231—C236—C235—C234	1.6 (5)
C231—C23—N23A—C24	−1.5 (5)	C236—C235—C234—C233	−0.4 (6)
N22—C23—N23A—C27A	0.7 (4)	C235—C234—C233—N232	−0.8 (6)
C231—C23—N23A—C27A	−179.1 (3)	C234—C233—N232—C231	0.7 (5)
C23—N23A—C24—C25	−179.9 (3)	C236—C231—N232—C233	0.6 (5)
C27A—N23A—C24—C25	−2.6 (5)	C23—C231—N232—C233	179.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cl2	0.98	2.79	3.746 (4)	167
C14—H14···N132	0.95	2.48	2.986 (4)	114
C17—H17···Cl3^i	0.95	2.68	3.450 (3)	139
C21—H21···Cl4^i	0.95	2.82	3.625 (3)	143
C22—H22A···Cl1^ii	0.98	2.79	3.378 (4)	120
C24—H24···Cl3	0.95	2.64	3.450 (4)	143
C24—H24···N232	0.95	2.43	2.955 (4)	115

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