Crystal structure of 1-[2-(4-chloro­phen­yl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

The mol­ecular and crystal structure of the title imidazole derivative is reported. The structure is stabilized by an extensive O—H...N, C—H...O/Cl and C—H...π(ring) hydrogen-bonding network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.071
• wR factor = 0.188
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00471 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H152   ..  O212    ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H242   ..  O112    ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H243   ..  CL24    ..       2.91 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         34 Ang3
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.881 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10 Report

Alert level G
PLAT793_ALERT_4_G The Model has Chirality at C112    (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C212    (Centro SPGR)          R Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters         13 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        137 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 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
   3 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Agilent (2014); cell refinement: CrysAlis PRO (Agilent (2014); data reduction: CrysAlis PRO (Agilent (2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010) and WinGX (Farrugia 2012).

1-[2-(4-Chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

Crystal data

C24H21ClN2O	Z = 4
Mr = 388.88	F(000) = 816
Triclinic, P1	Dx = 1.267 Mg m^−3
a = 12.0235 (8) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.4263 (7) Å	Cell parameters from 8456 reflections
c = 13.6588 (4) Å	θ = 3.3–76.0°
α = 90.297 (3)°	µ = 1.78 mm^−1
β = 98.481 (4)°	T = 100 K
γ = 110.480 (5)°	Block, colourless
V = 2039.16 (19) Å^3	0.26 × 0.17 × 0.12 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	8427 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	7077 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.046
Detector resolution: 10.3449 pixels mm^-1	θmax = 76.5°, θmin = 3.3°
ω scans	h = −14→15
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	k = −16→16
Tmin = 0.929, Tmax = 0.958	l = −16→17
20056 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.188	w = 1/[σ^2(Fo^2) + (0.0644P)^2 + 4.0157P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
8427 reflections	Δρmax = 0.61 e Å^−3
513 parameters	Δρmin = −0.38 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. 7 reflections with Fo >>> Fc were omitted from the final refinement cycles.

The large void volume is unexpected as no solvent appeared or has been SQUEEZED out. The final difference map was reasonably flat; see below:

Electron density synthesis with coefficients Fo-Fc

Highest peak 0.61 at 0.0329 0.0214 0.3946 [ 2.26 A from H152 ] Deepest hole -0.39 at 0.0342 0.2000 0.1384 [ 0.55 A from CL14 ]

Mean = 0.00, Rms deviation from mean = 0.08, Highest memory used = 7053 / 34831

Fourier peaks appended to .res file

x y z sof U Peak Distances to nearest atoms (including eq.)

Q1 1 0.9671 0.9786 0.6054 1.00000 0.05 0.61 2.26 H152 2.55 H153 2.68 C152 2.83 C153 Q2 1 1.0187 1.1772 0.8923 1.00000 0.05 0.55 2.13 H143 2.54 H252 2.60 H253 2.79 C143 Q3 1 0.9545 0.5837 1.0817 1.00000 0.05 0.40 0.69 C244 0.98 C245 1.18 H244 1.48 H245 Q4 1 0.5215 0.9173 1.1876 1.00000 0.05 0.40 1.03 H22O 1.29 O212 1.55 H212 1.65 C212 Q5 1 0.4633 1.0258 1.1059 1.00000 0.05 0.39 1.05 H21E 1.93 C213 2.36 H22O 2.38 H21D Q6 1 0.4358 0.4634 1.1908 1.00000 0.05 0.38 1.24 N23 1.47 H226 1.55 C22 1.83 H12O Q7 1 0.4296 0.9995 0.7074 1.00000 0.05 0.37 1.27 H122 1.39 N13 1.69 C12 1.70 C122 Q8 1 0.5533 0.7461 0.3069 1.00000 0.05 0.36 0.79 H155 1.07 C155 1.57 C156 1.69 H156 Q9 1 0.5676 0.7949 0.7972 1.00000 0.05 0.35 0.73 H255 1.16 C255 1.69 C256 1.77 H256 Q10 1 0.4633 0.4418 0.6084 1.00000 0.05 0.35 0.95 H11C 1.87 C113 2.32 H11D 2.32 H11D

Shortest distances between peaks (including symmetry equivalents)

4 7 1.71 4 5 2.09 8 10 2.74 5 7 2.76 5 9 2.90 6 10 2.92 4 8 2.93

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

	x	y	z	Uiso*/Ueq
N11	0.4623 (2)	0.81917 (18)	0.10692 (17)	0.0206 (5)
C111	0.3879 (3)	0.7109 (2)	0.0663 (2)	0.0217 (6)
H11A	0.3799	0.7087	−0.0069	0.026*
H11B	0.3065	0.6925	0.0840	0.026*
C112	0.4415 (3)	0.6284 (2)	0.1053 (2)	0.0229 (6)
H112	0.5267	0.6510	0.0934	0.027*
O112	0.4398 (2)	0.62826 (17)	0.20851 (15)	0.0244 (4)
H12O	0.450 (4)	0.577 (4)	0.233 (3)	0.037*
C113	0.3704 (3)	0.5195 (2)	0.0524 (2)	0.0306 (7)
H11C	0.4005	0.4661	0.0832	0.046*
H11D	0.3800	0.5220	−0.0177	0.046*
H11E	0.2851	0.5004	0.0576	0.046*
C12	0.4413 (3)	0.8817 (2)	0.1760 (2)	0.0204 (5)
C121	0.3326 (3)	0.8574 (2)	0.2233 (2)	0.0225 (6)
C122	0.2886 (3)	0.9401 (2)	0.2337 (2)	0.0254 (6)
H122	0.3273	1.0071	0.2084	0.030*
C123	0.1899 (3)	0.9258 (3)	0.2803 (2)	0.0294 (6)
H123	0.1604	0.9821	0.2865	0.035*
C124	0.1348 (3)	0.8281 (3)	0.3175 (2)	0.0297 (7)
Cl14	0.01324 (8)	0.81097 (7)	0.37944 (7)	0.0422 (2)
C125	0.1763 (3)	0.7448 (2)	0.3090 (2)	0.0303 (7)
H125	0.1376	0.6783	0.3351	0.036*
C126	0.2752 (3)	0.7594 (2)	0.2616 (2)	0.0252 (6)
H126	0.3040	0.7026	0.2552	0.030*
N13	0.5298 (2)	0.97600 (19)	0.19205 (18)	0.0221 (5)
C14	0.6116 (3)	0.9743 (2)	0.1323 (2)	0.0215 (6)
C141	0.7228 (3)	1.0659 (2)	0.1281 (2)	0.0219 (6)
C142	0.7583 (3)	1.0951 (2)	0.0365 (2)	0.0258 (6)
H142	0.7095	1.0569	−0.0225	0.031*
C143	0.8643 (3)	1.1796 (2)	0.0304 (2)	0.0291 (6)
H143	0.8868	1.1994	−0.0325	0.035*
C144	0.9373 (3)	1.2353 (2)	0.1166 (3)	0.0295 (7)
H144	1.0106	1.2921	0.1130	0.035*
C145	0.9017 (3)	1.2068 (2)	0.2084 (2)	0.0287 (6)
H145	0.9507	1.2449	0.2675	0.034*
C146	0.7951 (3)	1.1232 (2)	0.2139 (2)	0.0261 (6)
H146	0.7712	1.1048	0.2767	0.031*
C15	0.5722 (3)	0.8776 (2)	0.0793 (2)	0.0208 (5)
C151	0.6323 (3)	0.8381 (2)	0.0091 (2)	0.0216 (6)
C152	0.5807 (3)	0.8094 (2)	−0.0905 (2)	0.0233 (6)
H152	0.5031	0.8113	−0.1141	0.028*
C153	0.6438 (3)	0.7782 (2)	−0.1547 (2)	0.0268 (6)
H153	0.6087	0.7584	−0.2222	0.032*
C154	0.7570 (3)	0.7758 (3)	−0.1214 (3)	0.0317 (7)
H154	0.7992	0.7541	−0.1658	0.038*
C155	0.8089 (3)	0.8048 (3)	−0.0231 (3)	0.0335 (7)
H155	0.8869	0.8035	−0.0004	0.040*
C156	0.7470 (3)	0.8359 (3)	0.0423 (2)	0.0269 (6)
H156	0.7828	0.8557	0.1097	0.032*
N21	0.4612 (2)	0.65591 (18)	0.60387 (18)	0.0214 (5)
C211	0.3840 (3)	0.7139 (2)	0.5615 (2)	0.0234 (6)
H21A	0.3028	0.6797	0.5792	0.028*
H21B	0.3761	0.7086	0.4883	0.028*
C212	0.4327 (3)	0.8315 (2)	0.5977 (2)	0.0267 (6)
H212	0.5178	0.8643	0.5859	0.032*
O212	0.4308 (2)	0.83421 (17)	0.70054 (16)	0.0261 (4)
H22O	0.448 (4)	0.895 (4)	0.723 (3)	0.039*
C213	0.3580 (4)	0.8907 (3)	0.5418 (3)	0.0343 (7)
H21C	0.2734	0.8558	0.5490	0.051*
H21D	0.3658	0.8898	0.4714	0.051*
H21E	0.3868	0.9646	0.5691	0.051*
C22	0.4392 (3)	0.5779 (2)	0.6698 (2)	0.0209 (5)
C221	0.3353 (3)	0.5378 (2)	0.7228 (2)	0.0226 (6)
C222	0.2854 (3)	0.6057 (2)	0.7629 (2)	0.0233 (6)
H222	0.3134	0.6794	0.7510	0.028*
C223	0.1948 (3)	0.5652 (2)	0.8201 (2)	0.0260 (6)
H223	0.1613	0.6112	0.8477	0.031*
C224	0.1539 (3)	0.4582 (3)	0.8365 (2)	0.0278 (6)
Cl24	0.04309 (7)	0.40905 (7)	0.91146 (6)	0.0352 (2)
C225	0.2008 (3)	0.3891 (2)	0.7968 (2)	0.0279 (6)
H225	0.1714	0.3154	0.8082	0.034*
C226	0.2911 (3)	0.4297 (2)	0.7401 (2)	0.0257 (6)
H226	0.3238	0.3830	0.7125	0.031*
N23	0.5282 (2)	0.53968 (19)	0.68408 (18)	0.0223 (5)
C24	0.6107 (3)	0.5952 (2)	0.6257 (2)	0.0218 (6)
C241	0.7235 (3)	0.5762 (2)	0.6227 (2)	0.0243 (6)
C242	0.7849 (3)	0.5493 (2)	0.7075 (2)	0.0254 (6)
H242	0.7522	0.5411	0.7674	0.031*
C243	0.8928 (3)	0.5345 (2)	0.7052 (3)	0.0296 (7)
H243	0.9330	0.5154	0.7632	0.036*
C244	0.9431 (3)	0.5475 (3)	0.6176 (3)	0.0327 (7)
H244	1.0184	0.5396	0.6165	0.039*
C245	0.8820 (3)	0.5719 (3)	0.5334 (3)	0.0356 (8)
H245	0.9147	0.5794	0.4734	0.043*
C246	0.7726 (3)	0.5858 (3)	0.5351 (2)	0.0295 (7)
H246	0.7310	0.6019	0.4762	0.035*
C25	0.5715 (3)	0.6682 (2)	0.5762 (2)	0.0218 (6)
C251	0.6349 (3)	0.7504 (2)	0.5120 (2)	0.0229 (6)
C252	0.7451 (3)	0.8269 (2)	0.5516 (2)	0.0276 (6)
H252	0.7752	0.8286	0.6201	0.033*
C253	0.8116 (3)	0.9009 (3)	0.4924 (3)	0.0342 (7)
H253	0.8868	0.9528	0.5202	0.041*
C254	0.7675 (3)	0.8988 (3)	0.3917 (3)	0.0341 (7)
H254	0.8130	0.9488	0.3506	0.041*
C255	0.6571 (3)	0.8234 (3)	0.3518 (2)	0.0307 (7)
H255	0.6269	0.8224	0.2834	0.037*
C256	0.5905 (3)	0.7494 (2)	0.4111 (2)	0.0263 (6)
H256	0.5149	0.6982	0.3833	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0264 (12)	0.0161 (11)	0.0195 (11)	0.0071 (9)	0.0054 (9)	0.0044 (9)
C111	0.0261 (14)	0.0165 (12)	0.0216 (13)	0.0065 (11)	0.0038 (11)	0.0033 (10)
C112	0.0298 (15)	0.0190 (13)	0.0211 (14)	0.0095 (11)	0.0060 (11)	0.0047 (11)
O112	0.0364 (12)	0.0204 (10)	0.0198 (10)	0.0138 (9)	0.0052 (8)	0.0065 (8)
C113	0.0407 (18)	0.0206 (14)	0.0297 (16)	0.0099 (13)	0.0058 (13)	0.0019 (12)
C12	0.0253 (14)	0.0176 (12)	0.0197 (13)	0.0085 (11)	0.0059 (10)	0.0063 (10)
C121	0.0270 (14)	0.0218 (13)	0.0199 (13)	0.0088 (11)	0.0066 (11)	0.0036 (11)
C122	0.0339 (16)	0.0181 (13)	0.0263 (15)	0.0101 (12)	0.0088 (12)	0.0045 (11)
C123	0.0307 (16)	0.0251 (15)	0.0355 (17)	0.0120 (12)	0.0099 (13)	0.0005 (13)
C124	0.0296 (16)	0.0277 (15)	0.0316 (16)	0.0064 (12)	0.0137 (13)	−0.0014 (12)
Cl14	0.0359 (4)	0.0339 (4)	0.0567 (6)	0.0050 (3)	0.0257 (4)	−0.0047 (4)
C125	0.0360 (17)	0.0204 (14)	0.0335 (17)	0.0057 (12)	0.0126 (13)	0.0024 (12)
C126	0.0301 (15)	0.0190 (13)	0.0276 (15)	0.0081 (11)	0.0093 (12)	0.0037 (11)
N13	0.0290 (13)	0.0195 (11)	0.0202 (11)	0.0101 (10)	0.0075 (9)	0.0041 (9)
C14	0.0291 (15)	0.0195 (13)	0.0183 (13)	0.0104 (11)	0.0065 (11)	0.0063 (10)
C141	0.0265 (14)	0.0184 (13)	0.0243 (14)	0.0110 (11)	0.0077 (11)	0.0065 (11)
C142	0.0308 (15)	0.0227 (14)	0.0254 (15)	0.0098 (12)	0.0075 (12)	0.0081 (11)
C143	0.0339 (16)	0.0244 (14)	0.0318 (16)	0.0098 (13)	0.0148 (13)	0.0110 (12)
C144	0.0304 (16)	0.0174 (13)	0.0411 (18)	0.0069 (12)	0.0106 (13)	0.0074 (12)
C145	0.0312 (16)	0.0212 (14)	0.0334 (17)	0.0087 (12)	0.0056 (13)	0.0009 (12)
C146	0.0350 (16)	0.0220 (14)	0.0236 (14)	0.0115 (12)	0.0078 (12)	0.0038 (11)
C15	0.0251 (14)	0.0186 (13)	0.0204 (13)	0.0087 (11)	0.0065 (11)	0.0065 (10)
C151	0.0292 (14)	0.0155 (12)	0.0223 (14)	0.0088 (11)	0.0093 (11)	0.0056 (10)
C152	0.0300 (15)	0.0187 (13)	0.0228 (14)	0.0090 (11)	0.0077 (11)	0.0058 (11)
C153	0.0378 (17)	0.0218 (14)	0.0212 (14)	0.0094 (12)	0.0090 (12)	0.0027 (11)
C154	0.0410 (18)	0.0295 (16)	0.0319 (17)	0.0173 (14)	0.0156 (14)	0.0032 (13)
C155	0.0331 (17)	0.0410 (18)	0.0330 (17)	0.0203 (15)	0.0075 (13)	0.0014 (14)
C156	0.0312 (16)	0.0299 (15)	0.0229 (14)	0.0143 (13)	0.0058 (12)	0.0046 (12)
N21	0.0289 (13)	0.0165 (11)	0.0205 (11)	0.0101 (9)	0.0043 (9)	0.0034 (9)
C211	0.0296 (15)	0.0228 (14)	0.0202 (13)	0.0130 (12)	0.0025 (11)	0.0052 (11)
C212	0.0361 (16)	0.0235 (14)	0.0238 (15)	0.0136 (12)	0.0076 (12)	0.0063 (11)
O212	0.0387 (12)	0.0171 (10)	0.0235 (10)	0.0103 (9)	0.0067 (9)	0.0032 (8)
C213	0.051 (2)	0.0293 (16)	0.0306 (17)	0.0239 (15)	0.0081 (15)	0.0063 (13)
C22	0.0269 (14)	0.0157 (12)	0.0193 (13)	0.0070 (11)	0.0030 (11)	0.0016 (10)
C221	0.0281 (14)	0.0202 (13)	0.0196 (13)	0.0085 (11)	0.0039 (11)	0.0062 (10)
C222	0.0286 (15)	0.0198 (13)	0.0233 (14)	0.0105 (11)	0.0050 (11)	0.0059 (11)
C223	0.0282 (15)	0.0269 (15)	0.0260 (15)	0.0130 (12)	0.0059 (12)	0.0072 (12)
C224	0.0273 (15)	0.0289 (15)	0.0268 (15)	0.0080 (12)	0.0080 (12)	0.0113 (12)
Cl24	0.0329 (4)	0.0368 (4)	0.0394 (4)	0.0123 (3)	0.0157 (3)	0.0182 (3)
C225	0.0339 (16)	0.0198 (14)	0.0290 (15)	0.0077 (12)	0.0059 (12)	0.0078 (11)
C226	0.0341 (16)	0.0193 (13)	0.0257 (15)	0.0120 (12)	0.0046 (12)	0.0043 (11)
N23	0.0304 (13)	0.0182 (11)	0.0208 (12)	0.0106 (10)	0.0065 (10)	0.0058 (9)
C24	0.0303 (15)	0.0186 (13)	0.0180 (13)	0.0101 (11)	0.0048 (11)	0.0031 (10)
C241	0.0299 (15)	0.0177 (13)	0.0271 (15)	0.0093 (11)	0.0080 (12)	0.0055 (11)
C242	0.0287 (15)	0.0206 (13)	0.0293 (15)	0.0102 (11)	0.0079 (12)	0.0081 (11)
C243	0.0291 (16)	0.0205 (14)	0.0392 (18)	0.0087 (12)	0.0054 (13)	0.0048 (12)
C244	0.0313 (16)	0.0236 (15)	0.049 (2)	0.0151 (13)	0.0103 (14)	−0.0058 (14)
C245	0.045 (2)	0.0314 (17)	0.0376 (18)	0.0164 (15)	0.0217 (15)	0.0055 (14)
C246	0.0420 (18)	0.0286 (15)	0.0254 (15)	0.0191 (14)	0.0118 (13)	0.0056 (12)
C25	0.0275 (14)	0.0186 (13)	0.0203 (13)	0.0090 (11)	0.0047 (11)	0.0017 (10)
C251	0.0308 (15)	0.0201 (13)	0.0224 (14)	0.0132 (11)	0.0076 (11)	0.0062 (11)
C252	0.0346 (16)	0.0252 (14)	0.0252 (15)	0.0122 (13)	0.0068 (12)	0.0042 (12)
C253	0.0353 (17)	0.0254 (15)	0.0439 (19)	0.0091 (13)	0.0164 (15)	0.0075 (14)
C254	0.0447 (19)	0.0304 (16)	0.0388 (18)	0.0208 (15)	0.0231 (15)	0.0181 (14)
C255	0.0454 (19)	0.0328 (16)	0.0238 (15)	0.0238 (15)	0.0112 (13)	0.0127 (13)
C256	0.0370 (17)	0.0269 (14)	0.0208 (14)	0.0171 (13)	0.0082 (12)	0.0051 (11)

Geometric parameters (Å, º)

N11—C12	1.368 (4)	N21—C22	1.365 (4)
N11—C15	1.388 (4)	N21—C25	1.388 (4)
N11—C111	1.469 (4)	N21—C211	1.468 (4)
C111—C112	1.525 (4)	C211—C212	1.530 (4)
C111—H11A	0.9900	C211—H21A	0.9900
C111—H11B	0.9900	C211—H21B	0.9900
C112—O112	1.413 (3)	C212—O212	1.408 (4)
C112—C113	1.524 (4)	C212—C213	1.525 (4)
C112—H112	1.0000	C212—H212	1.0000
O112—H12O	0.80 (5)	O212—H22O	0.82 (5)
C113—H11C	0.9800	C213—H21C	0.9800
C113—H11D	0.9800	C213—H21D	0.9800
C113—H11E	0.9800	C213—H21E	0.9800
C12—N13	1.330 (4)	C22—N23	1.330 (4)
C12—C121	1.477 (4)	C22—C221	1.475 (4)
C121—C126	1.399 (4)	C221—C226	1.396 (4)
C121—C122	1.402 (4)	C221—C222	1.402 (4)
C122—C123	1.383 (4)	C222—C223	1.390 (4)
C122—H122	0.9500	C222—H222	0.9500
C123—C124	1.384 (5)	C223—C224	1.378 (4)
C123—H123	0.9500	C223—H223	0.9500
C124—C125	1.386 (5)	C224—C225	1.387 (5)
C124—Cl14	1.743 (3)	C224—Cl24	1.747 (3)
C125—C126	1.391 (4)	C225—C226	1.383 (4)
C125—H125	0.9500	C225—H225	0.9500
C126—H126	0.9500	C226—H226	0.9500
N13—C14	1.373 (4)	N23—C24	1.377 (4)
C14—C15	1.376 (4)	C24—C25	1.370 (4)
C14—C141	1.476 (4)	C24—C241	1.471 (4)
C141—C146	1.394 (4)	C241—C242	1.398 (4)
C141—C142	1.395 (4)	C241—C246	1.398 (4)
C142—C143	1.393 (4)	C242—C243	1.384 (4)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.395 (5)	C243—C244	1.403 (5)
C143—H143	0.9500	C243—H243	0.9500
C144—C145	1.396 (5)	C244—C245	1.376 (5)
C144—H144	0.9500	C244—H244	0.9500
C145—C146	1.391 (4)	C245—C246	1.396 (5)
C145—H145	0.9500	C245—H245	0.9500
C146—H146	0.9500	C246—H246	0.9500
C15—C151	1.480 (4)	C25—C251	1.478 (4)
C151—C156	1.397 (4)	C251—C252	1.390 (5)
C151—C152	1.401 (4)	C251—C256	1.401 (4)
C152—C153	1.391 (4)	C252—C253	1.387 (4)
C152—H152	0.9500	C252—H252	0.9500
C153—C154	1.382 (5)	C253—C254	1.395 (5)
C153—H153	0.9500	C253—H253	0.9500
C154—C155	1.386 (5)	C254—C255	1.387 (5)
C154—H154	0.9500	C254—H254	0.9500
C155—C156	1.392 (4)	C255—C256	1.388 (4)
C155—H155	0.9500	C255—H255	0.9500
C156—H156	0.9500	C256—H256	0.9500
C12—N11—C15	106.9 (2)	C22—N21—C25	107.0 (2)
C12—N11—C111	129.2 (2)	C22—N21—C211	129.2 (3)
C15—N11—C111	123.9 (2)	C25—N21—C211	123.6 (2)
N11—C111—C112	112.1 (2)	N21—C211—C212	112.9 (2)
N11—C111—H11A	109.2	N21—C211—H21A	109.0
C112—C111—H11A	109.2	C212—C211—H21A	109.0
N11—C111—H11B	109.2	N21—C211—H21B	109.0
C112—C111—H11B	109.2	C212—C211—H21B	109.0
H11A—C111—H11B	107.9	H21A—C211—H21B	107.8
O112—C112—C113	112.5 (2)	O212—C212—C213	112.7 (3)
O112—C112—C111	106.4 (2)	O212—C212—C211	106.5 (2)
C113—C112—C111	110.6 (3)	C213—C212—C211	110.5 (3)
O112—C112—H112	109.1	O212—C212—H212	109.0
C113—C112—H112	109.1	C213—C212—H212	109.0
C111—C112—H112	109.1	C211—C212—H212	109.0
C112—O112—H12O	113 (3)	C212—O212—H22O	111 (3)
C112—C113—H11C	109.5	C212—C213—H21C	109.5
C112—C113—H11D	109.5	C212—C213—H21D	109.5
H11C—C113—H11D	109.5	H21C—C213—H21D	109.5
C112—C113—H11E	109.5	C212—C213—H21E	109.5
H11C—C113—H11E	109.5	H21C—C213—H21E	109.5
H11D—C113—H11E	109.5	H21D—C213—H21E	109.5
N13—C12—N11	111.0 (2)	N23—C22—N21	110.8 (3)
N13—C12—C121	121.5 (3)	N23—C22—C221	121.3 (2)
N11—C12—C121	127.3 (3)	N21—C22—C221	127.9 (3)
C126—C121—C122	118.7 (3)	C226—C221—C222	118.8 (3)
C126—C121—C12	124.1 (3)	C226—C221—C22	118.7 (3)
C122—C121—C12	117.0 (3)	C222—C221—C22	122.3 (3)
C123—C122—C121	121.1 (3)	C223—C222—C221	119.9 (3)
C123—C122—H122	119.5	C223—C222—H222	120.0
C121—C122—H122	119.5	C221—C222—H222	120.0
C122—C123—C124	119.0 (3)	C224—C223—C222	119.8 (3)
C122—C123—H123	120.5	C224—C223—H223	120.1
C124—C123—H123	120.5	C222—C223—H223	120.1
C123—C124—C125	121.4 (3)	C223—C224—C225	121.4 (3)
C123—C124—Cl14	119.2 (3)	C223—C224—Cl24	119.3 (3)
C125—C124—Cl14	119.4 (2)	C225—C224—Cl24	119.3 (2)
C124—C125—C126	119.3 (3)	C226—C225—C224	118.7 (3)
C124—C125—H125	120.3	C226—C225—H225	120.7
C126—C125—H125	120.3	C224—C225—H225	120.7
C125—C126—C121	120.4 (3)	C225—C226—C221	121.3 (3)
C125—C126—H126	119.8	C225—C226—H226	119.3
C121—C126—H126	119.8	C221—C226—H226	119.3
C12—N13—C14	106.3 (2)	C22—N23—C24	106.4 (2)
N13—C14—C15	109.8 (3)	C25—C24—N23	109.7 (3)
N13—C14—C141	122.7 (3)	C25—C24—C241	127.9 (3)
C15—C14—C141	127.5 (3)	N23—C24—C241	122.5 (2)
C146—C141—C142	118.9 (3)	C242—C241—C246	118.4 (3)
C146—C141—C14	121.5 (3)	C242—C241—C24	120.9 (3)
C142—C141—C14	119.6 (3)	C246—C241—C24	120.7 (3)
C143—C142—C141	120.9 (3)	C243—C242—C241	120.8 (3)
C143—C142—H142	119.6	C243—C242—H242	119.6
C141—C142—H142	119.6	C241—C242—H242	119.6
C142—C143—C144	120.0 (3)	C242—C243—C244	120.3 (3)
C142—C143—H143	120.0	C242—C243—H243	119.8
C144—C143—H143	120.0	C244—C243—H243	119.8
C143—C144—C145	119.3 (3)	C245—C244—C243	119.1 (3)
C143—C144—H144	120.3	C245—C244—H244	120.4
C145—C144—H144	120.3	C243—C244—H244	120.4
C146—C145—C144	120.4 (3)	C244—C245—C246	120.7 (3)
C146—C145—H145	119.8	C244—C245—H245	119.7
C144—C145—H145	119.8	C246—C245—H245	119.7
C145—C146—C141	120.5 (3)	C245—C246—C241	120.6 (3)
C145—C146—H146	119.7	C245—C246—H246	119.7
C141—C146—H146	119.7	C241—C246—H246	119.7
C14—C15—N11	106.0 (2)	C24—C25—N21	106.1 (2)
C14—C15—C151	129.1 (3)	C24—C25—C251	128.5 (3)
N11—C15—C151	124.9 (3)	N21—C25—C251	125.3 (3)
C156—C151—C152	119.5 (3)	C252—C251—C256	119.1 (3)
C156—C151—C15	118.6 (3)	C252—C251—C25	119.0 (3)
C152—C151—C15	121.8 (3)	C256—C251—C25	121.8 (3)
C153—C152—C151	119.6 (3)	C253—C252—C251	121.0 (3)
C153—C152—H152	120.2	C253—C252—H252	119.5
C151—C152—H152	120.2	C251—C252—H252	119.5
C154—C153—C152	120.7 (3)	C252—C253—C254	119.6 (3)
C154—C153—H153	119.7	C252—C253—H253	120.2
C152—C153—H153	119.7	C254—C253—H253	120.2
C153—C154—C155	120.0 (3)	C255—C254—C253	119.8 (3)
C153—C154—H154	120.0	C255—C254—H254	120.1
C155—C154—H154	120.0	C253—C254—H254	120.1
C154—C155—C156	120.2 (3)	C254—C255—C256	120.5 (3)
C154—C155—H155	119.9	C254—C255—H255	119.7
C156—C155—H155	119.9	C256—C255—H255	119.7
C155—C156—C151	120.1 (3)	C255—C256—C251	120.0 (3)
C155—C156—H156	120.0	C255—C256—H256	120.0
C151—C156—H156	120.0	C251—C256—H256	120.0
C12—N11—C111—C112	−107.3 (3)	C22—N21—C211—C212	111.7 (3)
C15—N11—C111—C112	72.6 (3)	C25—N21—C211—C212	−72.8 (3)
N11—C111—C112—O112	64.4 (3)	N21—C211—C212—O212	−64.4 (3)
N11—C111—C112—C113	−173.2 (2)	N21—C211—C212—C213	172.9 (3)
C15—N11—C12—N13	1.1 (3)	C25—N21—C22—N23	−0.9 (3)
C111—N11—C12—N13	−179.0 (3)	C211—N21—C22—N23	175.1 (3)
C15—N11—C12—C121	176.0 (3)	C25—N21—C22—C221	178.1 (3)
C111—N11—C12—C121	−4.1 (5)	C211—N21—C22—C221	−5.9 (5)
N13—C12—C121—C126	−140.0 (3)	N23—C22—C221—C226	−36.8 (4)
N11—C12—C121—C126	45.6 (5)	N21—C22—C221—C226	144.3 (3)
N13—C12—C121—C122	37.1 (4)	N23—C22—C221—C222	138.1 (3)
N11—C12—C121—C122	−137.3 (3)	N21—C22—C221—C222	−40.7 (5)
C126—C121—C122—C123	−0.5 (5)	C226—C221—C222—C223	1.0 (4)
C12—C121—C122—C123	−177.7 (3)	C22—C221—C222—C223	−174.0 (3)
C121—C122—C123—C124	0.5 (5)	C221—C222—C223—C224	−0.5 (5)
C122—C123—C124—C125	−0.2 (5)	C222—C223—C224—C225	−0.3 (5)
C122—C123—C124—Cl14	178.1 (3)	C222—C223—C224—Cl24	178.2 (2)
C123—C124—C125—C126	−0.2 (5)	C223—C224—C225—C226	0.5 (5)
Cl14—C124—C125—C126	−178.5 (3)	Cl24—C224—C225—C226	−178.0 (2)
C124—C125—C126—C121	0.2 (5)	C224—C225—C226—C221	0.1 (5)
C122—C121—C126—C125	0.1 (5)	C222—C221—C226—C225	−0.8 (5)
C12—C121—C126—C125	177.1 (3)	C22—C221—C226—C225	174.3 (3)
N11—C12—N13—C14	−0.6 (3)	N21—C22—N23—C24	0.3 (3)
C121—C12—N13—C14	−175.9 (3)	C221—C22—N23—C24	−178.8 (3)
C12—N13—C14—C15	0.0 (3)	C22—N23—C24—C25	0.5 (3)
C12—N13—C14—C141	179.2 (3)	C22—N23—C24—C241	179.0 (3)
N13—C14—C141—C146	44.4 (4)	C25—C24—C241—C242	143.7 (3)
C15—C14—C141—C146	−136.5 (3)	N23—C24—C241—C242	−34.6 (4)
N13—C14—C141—C142	−136.9 (3)	C25—C24—C241—C246	−35.6 (5)
C15—C14—C141—C142	42.2 (4)	N23—C24—C241—C246	146.1 (3)
C146—C141—C142—C143	0.3 (4)	C246—C241—C242—C243	1.2 (5)
C14—C141—C142—C143	−178.4 (3)	C24—C241—C242—C243	−178.2 (3)
C141—C142—C143—C144	0.9 (5)	C241—C242—C243—C244	0.8 (5)
C142—C143—C144—C145	−1.3 (5)	C242—C243—C244—C245	−2.0 (5)
C143—C144—C145—C146	0.6 (5)	C243—C244—C245—C246	1.3 (5)
C144—C145—C146—C141	0.6 (5)	C244—C245—C246—C241	0.7 (5)
C142—C141—C146—C145	−1.0 (4)	C242—C241—C246—C245	−1.9 (5)
C14—C141—C146—C145	177.7 (3)	C24—C241—C246—C245	177.4 (3)
N13—C14—C15—N11	0.7 (3)	N23—C24—C25—N21	−1.0 (3)
C141—C14—C15—N11	−178.6 (3)	C241—C24—C25—N21	−179.5 (3)
N13—C14—C15—C151	−177.3 (3)	N23—C24—C25—C251	174.7 (3)
C141—C14—C15—C151	3.5 (5)	C241—C24—C25—C251	−3.8 (5)
C12—N11—C15—C14	−1.0 (3)	C22—N21—C25—C24	1.1 (3)
C111—N11—C15—C14	179.0 (2)	C211—N21—C25—C24	−175.2 (3)
C12—N11—C15—C151	177.0 (3)	C22—N21—C25—C251	−174.7 (3)
C111—N11—C15—C151	−2.9 (4)	C211—N21—C25—C251	9.0 (4)
C14—C15—C151—C156	56.7 (4)	C24—C25—C251—C252	−59.1 (4)
N11—C15—C151—C156	−120.9 (3)	N21—C25—C251—C252	115.8 (3)
C14—C15—C151—C152	−119.2 (3)	C24—C25—C251—C256	117.0 (4)
N11—C15—C151—C152	63.2 (4)	N21—C25—C251—C256	−68.1 (4)
C156—C151—C152—C153	0.7 (4)	C256—C251—C252—C253	−0.7 (5)
C15—C151—C152—C153	176.5 (3)	C25—C251—C252—C253	175.4 (3)
C151—C152—C153—C154	−0.4 (4)	C251—C252—C253—C254	0.0 (5)
C152—C153—C154—C155	−0.2 (5)	C252—C253—C254—C255	0.6 (5)
C153—C154—C155—C156	0.4 (5)	C253—C254—C255—C256	−0.6 (5)
C154—C155—C156—C151	−0.1 (5)	C254—C255—C256—C251	−0.2 (5)
C152—C151—C156—C155	−0.4 (4)	C252—C251—C256—C255	0.8 (4)
C15—C151—C156—C155	−176.4 (3)	C25—C251—C256—C255	−175.3 (3)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N11/C12/N13/C14/C15, N21/C22/N23/C24/C25, C221–C226 and C241–C246 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O112—H12O···N23^i	0.80 (5)	2.01 (5)	2.804 (3)	170 (4)
O212—H22O···N13^ii	0.82 (5)	1.99 (5)	2.790 (3)	165 (4)
C152—H152···O212^iii	0.95	2.61	3.227 (4)	123
C256—H256···O112	0.95	2.48	3.162 (4)	129
C242—H242···O112^i	0.95	2.68	3.277 (4)	122
C243—H243···Cl24^iv	0.95	2.91	3.836 (3)	166
C113—H11D···Cg6^iii	0.98	2.96	3.778 (3)	142
C153—H153···Cg5^iii	0.95	2.65	3.495 (3)	148
C213—H21D···Cg2	0.98	2.91	3.745 (4)	144
C255—H255···Cg1	0.95	2.65	3.505 (3)	149

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