Crystal structures of three 6-aryl-2-(4-chloro­benz­yl)-5-[(1H-indol-3-yl)meth­yl]imidazo[2,1-b][1,3,4]thia­diazo­les

In the crystals of three new 6-aryl-2-(4-chloro­benz­yl)-5-[(1H-indol-3-yl)meth­yl]imidazo[2,1-b][1,3,4]thia­diazo­les (where aryl is phenyl, 4-fluoro­phenyl or 4-bromo­phen­yl), the mol­ecules are linked by a combination of N—H...N and C—H...π inter­actions to form chains when the 6-aryl substituent is phenyl or 4-fluoro­phenyl and a three-dimensional framework when the 6-aryl group is 4-bromo­phenyl.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 302 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.177
• Data-to-parameter ratio = 17.2

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.131
• Data-to-parameter ratio = 15.6

Structure: III

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.100
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C156 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       C227 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C221 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C224 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C121     -C126            1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C131     -C136            1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C221     -C226            1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00411 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.745 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         39 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         24 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          8 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        25% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         18 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C21      -C26             1.36 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C35      ..CG1              4.06 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.347 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          8 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        24% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         23 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        207 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 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
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0065 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.925 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         68 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          8 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        24% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         18 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        232 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 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.

   1 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: APEX2 (Bruker, 2012) for (I); CrysAlis CCD (Oxford Diffraction, 2009) for (II), (III). Cell refinement: SAINT (Bruker, 2017) for (I); CrysAlis RED (Oxford Diffraction, 2009) for (II), (III). Data reduction: SAINT (Bruker, 2017) for (I); CrysAlis RED (Oxford Diffraction, 2009) for (II), (III). For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) for (I); SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009) for (II), (III).

2-(4-Chlorobenzyl)-5-[(1H-indol-3-yl)methyl]-6-phenylimidazo[2,1-b][1,3,4]thiadiazole (I)

Crystal data

C26H19ClN4S	F(000) = 1888
Mr = 454.96	Dx = 1.336 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.456 (7) Å	Cell parameters from 12458 reflections
b = 10.420 (2) Å	θ = 2.1–29.5°
c = 26.391 (7) Å	µ = 0.28 mm^−1
β = 90.031 (12)°	T = 302 K
V = 4525 (2) Å^3	Block, colourless
Z = 8	0.33 × 0.31 × 0.28 mm

Data collection

Bruker SMART X2S benchtop diffractometer	10420 independent reflections
Radiation source: fine-focus sealed tube	7091 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 7.3910 pixels mm^-1	θmax = 27.6°, θmin = 2.1°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2017)	k = −12→13
Tmin = 0.845, Tmax = 0.924	l = −34→34
55921 measured reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.177	w = 1/[σ^2(Fo^2) + (0.0741P)^2 + 2.5289P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
10420 reflections	Δρmax = 0.77 e Å^−3
605 parameters	Δρmin = −0.59 e Å^−3
18 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	Occ. (<1)
S11	0.31032 (5)	0.27517 (7)	0.84740 (2)	0.0673 (2)
C12	0.30411 (19)	0.1424 (2)	0.80654 (10)	0.0657 (7)
N13	0.31605 (14)	0.16395 (19)	0.75885 (8)	0.0592 (5)
N14	0.33131 (12)	0.29274 (18)	0.75295 (7)	0.0500 (4)
C15	0.35023 (13)	0.3678 (2)	0.71151 (8)	0.0479 (5)
C16	0.36495 (13)	0.4871 (2)	0.73223 (8)	0.0481 (5)
N17	0.35301 (12)	0.48713 (18)	0.78480 (7)	0.0516 (4)
C17A	0.33304 (14)	0.3679 (2)	0.79516 (8)	0.0514 (5)
C127	0.2866 (3)	0.0098 (3)	0.82642 (12)	0.1004 (12)	0.6289 (17)
H12A	0.3290	−0.0485	0.8154	0.121*	0.6289 (17)
H12B	0.2354	−0.0203	0.8126	0.121*	0.6289 (17)
C121	0.2822 (7)	0.009 (2)	0.88341 (16)	0.0601 (19)	0.6289 (17)
C122	0.2095 (4)	0.0462 (10)	0.90440 (18)	0.0712 (12)	0.6289 (17)
H122	0.1672	0.0698	0.8830	0.085*	0.6289 (17)
C123	0.1973 (4)	0.0495 (6)	0.95558 (18)	0.0795 (15)	0.6289 (17)
H123	0.1480	0.0776	0.9687	0.095*	0.6289 (17)
C124	0.2583 (4)	0.0110 (5)	0.98740 (18)	0.0750 (16)	0.6289 (17)
Cl14	0.23860 (15)	0.0201 (2)	1.05325 (5)	0.1395 (8)	0.6289 (17)
C125	0.3307 (5)	−0.0285 (9)	0.9695 (3)	0.098 (2)	0.6289 (17)
H125	0.3724	−0.0508	0.9916	0.118*	0.6289 (17)
C126	0.3419 (5)	−0.0352 (11)	0.9164 (2)	0.0913 (19)	0.6289 (17)
H126	0.3897	−0.0696	0.9034	0.110*	0.6289 (17)
C137	0.2866 (3)	0.0098 (3)	0.82642 (12)	0.1004 (12)	0.3711 (17)
H13A	0.2334	−0.0154	0.8141	0.121*	0.3711 (17)
H13B	0.3258	−0.0484	0.8115	0.121*	0.3711 (17)
C131	0.2878 (12)	−0.010 (4)	0.8818 (3)	0.0601 (19)	0.3711 (17)
C132	0.2312 (7)	0.0348 (19)	0.9149 (3)	0.0712 (12)	0.3711 (17)
H132	0.1853	0.0761	0.9023	0.085*	0.3711 (17)
C133	0.2404 (7)	0.0206 (11)	0.9664 (3)	0.0795 (15)	0.3711 (17)
H133	0.2012	0.0485	0.9892	0.095*	0.3711 (17)
C134	0.3110 (8)	−0.0370 (14)	0.9822 (3)	0.0750 (16)	0.3711 (17)
Cl34	0.3237 (3)	−0.0678 (4)	1.04645 (9)	0.1395 (8)	0.3711 (17)
C135	0.3710 (6)	−0.0735 (11)	0.9502 (4)	0.098 (2)	0.3711 (17)
H135	0.4177	−0.1122	0.9630	0.118*	0.3711 (17)
C136	0.3629 (8)	−0.053 (2)	0.8992 (4)	0.0913 (19)	0.3711 (17)
H136	0.4059	−0.0679	0.8770	0.110*	0.3711 (17)
C151	0.34906 (14)	0.3156 (2)	0.65887 (8)	0.0530 (5)
H15A	0.3398	0.3856	0.6354	0.064*
H15B	0.3040	0.2562	0.6557	0.064*
N151	0.54541 (16)	0.1450 (2)	0.64974 (10)	0.0714 (6)
H151	0.582 (2)	0.102 (3)	0.6632 (12)	0.086*
C152	0.48211 (17)	0.1970 (3)	0.67633 (10)	0.0632 (6)
H152	0.4780	0.1975	0.7115	0.076*
C153	0.42624 (15)	0.2478 (2)	0.64434 (9)	0.0511 (5)
C15A	0.45586 (16)	0.2239 (2)	0.59416 (9)	0.0556 (6)
C154	0.4266 (2)	0.2512 (3)	0.54534 (10)	0.0778 (8)
H154	0.3778	0.2946	0.5409	0.093*
C155	0.4714 (3)	0.2129 (5)	0.50439 (13)	0.1129 (14)
H155	0.4522	0.2300	0.4719	0.135*
C156	0.5450 (3)	0.1491 (5)	0.51017 (15)	0.1260 (16)
H156	0.5738	0.1243	0.4815	0.151*
C157	0.5760 (2)	0.1219 (4)	0.55721 (15)	0.0997 (11)
H157	0.6256	0.0800	0.5609	0.120*
C15B	0.53082 (18)	0.1590 (3)	0.59925 (11)	0.0659 (7)
C161	0.39381 (14)	0.6037 (2)	0.70655 (9)	0.0523 (5)
C162	0.43854 (18)	0.5967 (3)	0.66191 (11)	0.0734 (8)
H162	0.4498	0.5172	0.6476	0.088*
C163	0.4663 (2)	0.7074 (4)	0.63880 (14)	0.0967 (11)
H163	0.4949	0.7016	0.6085	0.116*
C164	0.4523 (2)	0.8252 (3)	0.65985 (14)	0.0920 (10)
H164	0.4714	0.8991	0.6440	0.110*
C165	0.41005 (19)	0.8339 (3)	0.70429 (13)	0.0774 (8)
H165	0.4013	0.9136	0.7191	0.093*
C166	0.38022 (16)	0.7241 (2)	0.72725 (11)	0.0613 (6)
H166	0.3505	0.7312	0.7571	0.074*
S21	0.81319 (5)	0.26550 (6)	0.36890 (2)	0.06146 (19)
C22	0.79667 (16)	0.1410 (2)	0.32528 (9)	0.0556 (6)
N23	0.80388 (12)	0.16982 (18)	0.27773 (7)	0.0521 (5)
N24	0.82302 (11)	0.29774 (17)	0.27438 (7)	0.0464 (4)
C25	0.83901 (13)	0.3782 (2)	0.23401 (8)	0.0454 (5)
C26	0.85977 (13)	0.4923 (2)	0.25691 (9)	0.0471 (5)
N27	0.85510 (12)	0.48486 (17)	0.30993 (7)	0.0510 (4)
C27A	0.83258 (14)	0.3658 (2)	0.31816 (8)	0.0488 (5)
C227	0.7712 (2)	0.0096 (3)	0.34268 (10)	0.0756 (8)
H27A	0.7934	−0.0536	0.3195	0.091*
H27B	0.7124	0.0038	0.3409	0.091*
C221	0.79792 (17)	−0.0234 (2)	0.39582 (9)	0.0581 (6)
C222	0.7412 (2)	−0.0349 (3)	0.43409 (12)	0.0789 (8)
H222	0.6865	−0.0214	0.4270	0.095*
C223	0.7651 (2)	−0.0666 (3)	0.48308 (12)	0.0879 (10)
H223	0.7265	−0.0758	0.5086	0.105*
C224	0.8451 (2)	−0.0840 (3)	0.49320 (11)	0.0752 (8)
Cl24	0.87453 (9)	−0.12121 (10)	0.55515 (3)	0.1245 (4)
C225	0.9020 (2)	−0.0732 (3)	0.45637 (12)	0.0780 (8)
H225	0.9567	−0.0858	0.4638	0.094*
C226	0.87801 (19)	−0.0434 (3)	0.40794 (11)	0.0699 (7)
H226	0.9171	−0.0366	0.3827	0.084*
C251	0.82542 (14)	0.3397 (2)	0.18012 (8)	0.0495 (5)
H25A	0.8160	0.4166	0.1602	0.059*
H25B	0.7765	0.2880	0.1784	0.059*
N251	1.00742 (14)	0.1509 (2)	0.14489 (9)	0.0629 (6)
H251	1.0492 (18)	0.111 (3)	0.1531 (11)	0.075*
C252	0.95708 (15)	0.2074 (2)	0.17995 (9)	0.0544 (6)
H252	0.9652	0.2060	0.2148	0.065*
C253	0.89371 (14)	0.2656 (2)	0.15627 (8)	0.0465 (5)
C25A	0.90401 (16)	0.2437 (2)	0.10308 (9)	0.0514 (5)
C254	0.8607 (2)	0.2795 (3)	0.05983 (10)	0.0694 (7)
H254	0.8129	0.3268	0.0625	0.083*
C255	0.8900 (3)	0.2433 (3)	0.01311 (11)	0.0889 (11)
H255	0.8618	0.2675	−0.0159	0.107*
C256	0.9603 (3)	0.1721 (3)	0.00835 (12)	0.0948 (12)
H256	0.9782	0.1488	−0.0238	0.114*
C257	1.0041 (2)	0.1350 (3)	0.04969 (12)	0.0810 (9)
H257	1.0512	0.0867	0.0462	0.097*
C25B	0.97612 (17)	0.1717 (2)	0.09748 (10)	0.0589 (6)
C261	0.88792 (14)	0.6111 (2)	0.23229 (9)	0.0517 (5)
C262	0.93528 (16)	0.6056 (3)	0.18874 (10)	0.0625 (6)
H262	0.9476	0.5264	0.1744	0.075*
C263	0.96429 (19)	0.7166 (3)	0.16649 (12)	0.0762 (8)
H263	0.9953	0.7115	0.1371	0.091*
C264	0.9476 (2)	0.8343 (3)	0.18741 (14)	0.0822 (9)
H264	0.9676	0.9088	0.1725	0.099*
C265	0.9009 (2)	0.8412 (3)	0.23078 (14)	0.0802 (9)
H265	0.8896	0.9206	0.2452	0.096*
C266	0.87069 (16)	0.7304 (2)	0.25296 (11)	0.0631 (7)
H266	0.8387	0.7361	0.2819	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S11	0.1014 (5)	0.0572 (4)	0.0434 (3)	−0.0198 (3)	0.0077 (3)	−0.0023 (3)
C12	0.094 (2)	0.0527 (14)	0.0504 (14)	−0.0186 (13)	0.0030 (13)	−0.0018 (11)
N13	0.0783 (14)	0.0487 (11)	0.0505 (11)	−0.0157 (10)	0.0016 (10)	−0.0024 (9)
N14	0.0599 (11)	0.0476 (10)	0.0425 (10)	−0.0103 (9)	0.0012 (8)	−0.0028 (8)
C15	0.0486 (12)	0.0510 (12)	0.0440 (11)	−0.0023 (10)	0.0021 (9)	0.0002 (9)
C16	0.0457 (11)	0.0505 (12)	0.0480 (12)	−0.0026 (9)	0.0028 (9)	0.0013 (9)
N17	0.0580 (11)	0.0484 (10)	0.0482 (10)	−0.0080 (9)	0.0040 (8)	−0.0035 (8)
C17A	0.0587 (13)	0.0510 (13)	0.0445 (12)	−0.0105 (10)	0.0028 (10)	−0.0044 (10)
C127	0.178 (4)	0.0584 (18)	0.0645 (19)	−0.034 (2)	0.018 (2)	0.0031 (14)
C121	0.086 (2)	0.035 (7)	0.0592 (15)	−0.0090 (16)	−0.0037 (14)	0.0072 (15)
C122	0.066 (4)	0.082 (3)	0.065 (3)	−0.003 (3)	−0.018 (2)	0.023 (3)
C123	0.087 (4)	0.095 (4)	0.056 (3)	−0.020 (3)	−0.001 (3)	0.024 (2)
C124	0.104 (5)	0.070 (3)	0.052 (2)	−0.031 (3)	−0.022 (3)	0.022 (2)
Cl14	0.213 (2)	0.1510 (16)	0.0543 (6)	−0.0869 (14)	−0.0184 (10)	0.0230 (8)
C125	0.115 (7)	0.078 (4)	0.102 (6)	0.000 (4)	−0.035 (4)	0.024 (4)
C126	0.076 (4)	0.076 (4)	0.121 (5)	0.015 (3)	0.005 (4)	0.022 (5)
C137	0.178 (4)	0.0584 (18)	0.0645 (19)	−0.034 (2)	0.018 (2)	0.0031 (14)
C131	0.086 (2)	0.035 (7)	0.0592 (15)	−0.0090 (16)	−0.0037 (14)	0.0072 (15)
C132	0.066 (4)	0.082 (3)	0.065 (3)	−0.003 (3)	−0.018 (2)	0.023 (3)
C133	0.087 (4)	0.095 (4)	0.056 (3)	−0.020 (3)	−0.001 (3)	0.024 (2)
C134	0.104 (5)	0.070 (3)	0.052 (2)	−0.031 (3)	−0.022 (3)	0.022 (2)
Cl34	0.213 (2)	0.1510 (16)	0.0543 (6)	−0.0869 (14)	−0.0184 (10)	0.0230 (8)
C135	0.115 (7)	0.078 (4)	0.102 (6)	0.000 (4)	−0.035 (4)	0.024 (4)
C136	0.076 (4)	0.076 (4)	0.121 (5)	0.015 (3)	0.005 (4)	0.022 (5)
C151	0.0577 (13)	0.0603 (14)	0.0409 (11)	−0.0030 (11)	−0.0025 (10)	−0.0014 (10)
N151	0.0752 (16)	0.0659 (14)	0.0733 (16)	0.0193 (12)	−0.0010 (12)	0.0093 (12)
C152	0.0718 (16)	0.0667 (16)	0.0511 (14)	0.0077 (13)	0.0001 (12)	0.0065 (12)
C153	0.0605 (14)	0.0484 (12)	0.0445 (12)	−0.0014 (10)	−0.0005 (10)	0.0005 (9)
C15A	0.0670 (15)	0.0509 (13)	0.0488 (13)	−0.0002 (11)	0.0047 (11)	0.0002 (10)
C154	0.094 (2)	0.093 (2)	0.0467 (14)	0.0082 (17)	0.0049 (14)	0.0025 (14)
C155	0.130 (3)	0.156 (4)	0.0524 (18)	0.025 (3)	0.015 (2)	−0.001 (2)
C156	0.142 (4)	0.161 (4)	0.075 (2)	0.040 (3)	0.035 (3)	−0.016 (3)
C157	0.100 (3)	0.105 (3)	0.094 (3)	0.031 (2)	0.024 (2)	−0.015 (2)
C15B	0.0782 (18)	0.0537 (14)	0.0657 (16)	0.0070 (13)	0.0097 (14)	−0.0016 (12)
C161	0.0487 (12)	0.0536 (13)	0.0546 (13)	−0.0038 (10)	−0.0002 (10)	0.0062 (10)
C162	0.0811 (19)	0.0667 (17)	0.0724 (18)	−0.0116 (14)	0.0222 (15)	0.0034 (14)
C163	0.116 (3)	0.092 (3)	0.082 (2)	−0.021 (2)	0.035 (2)	0.0145 (19)
C164	0.107 (3)	0.070 (2)	0.099 (3)	−0.0243 (18)	0.007 (2)	0.0288 (19)
C165	0.088 (2)	0.0534 (16)	0.091 (2)	−0.0062 (14)	−0.0023 (17)	0.0095 (15)
C166	0.0637 (15)	0.0519 (14)	0.0682 (16)	−0.0022 (11)	0.0015 (12)	0.0043 (12)
S21	0.0877 (5)	0.0533 (3)	0.0434 (3)	−0.0120 (3)	−0.0005 (3)	−0.0058 (2)
C22	0.0720 (16)	0.0473 (12)	0.0476 (13)	−0.0083 (11)	−0.0047 (11)	−0.0031 (10)
N23	0.0657 (12)	0.0418 (10)	0.0489 (11)	−0.0065 (9)	−0.0043 (9)	−0.0037 (8)
N24	0.0547 (10)	0.0406 (9)	0.0438 (10)	−0.0061 (8)	−0.0006 (8)	−0.0058 (7)
C25	0.0476 (12)	0.0429 (11)	0.0457 (11)	0.0008 (9)	−0.0009 (9)	−0.0029 (9)
C26	0.0456 (11)	0.0432 (11)	0.0524 (12)	0.0004 (9)	0.0006 (9)	−0.0034 (9)
N27	0.0597 (11)	0.0442 (10)	0.0490 (10)	−0.0041 (8)	−0.0002 (9)	−0.0089 (8)
C27A	0.0570 (13)	0.0468 (12)	0.0424 (11)	−0.0033 (10)	−0.0019 (9)	−0.0066 (9)
C227	0.114 (2)	0.0543 (15)	0.0585 (16)	−0.0228 (15)	−0.0099 (15)	0.0050 (12)
C221	0.0779 (17)	0.0439 (12)	0.0524 (13)	−0.0079 (11)	0.0025 (12)	−0.0008 (10)
C222	0.0716 (18)	0.089 (2)	0.0762 (19)	−0.0084 (16)	0.0064 (15)	0.0005 (16)
C223	0.110 (3)	0.093 (2)	0.0607 (18)	−0.013 (2)	0.0310 (18)	0.0006 (16)
C224	0.116 (3)	0.0518 (15)	0.0579 (16)	−0.0069 (16)	−0.0052 (17)	0.0053 (12)
Cl24	0.2214 (13)	0.0858 (6)	0.0662 (5)	−0.0033 (7)	−0.0249 (6)	0.0174 (4)
C225	0.089 (2)	0.0626 (17)	0.083 (2)	0.0063 (15)	−0.0084 (17)	0.0093 (15)
C226	0.0783 (19)	0.0632 (16)	0.0682 (17)	0.0017 (14)	0.0153 (14)	0.0066 (13)
C251	0.0540 (12)	0.0501 (12)	0.0446 (11)	0.0001 (10)	−0.0048 (9)	−0.0019 (9)
N251	0.0663 (13)	0.0551 (12)	0.0671 (14)	0.0146 (10)	0.0065 (11)	0.0045 (10)
C252	0.0621 (14)	0.0533 (13)	0.0480 (12)	0.0060 (11)	0.0009 (11)	0.0044 (10)
C253	0.0586 (13)	0.0399 (11)	0.0411 (11)	−0.0010 (9)	−0.0007 (9)	−0.0005 (8)
C25A	0.0741 (15)	0.0360 (11)	0.0442 (12)	−0.0035 (10)	0.0008 (11)	−0.0020 (9)
C254	0.105 (2)	0.0556 (15)	0.0473 (14)	−0.0033 (14)	−0.0139 (14)	−0.0021 (11)
C255	0.153 (3)	0.0666 (19)	0.0467 (15)	−0.014 (2)	−0.0099 (18)	−0.0047 (13)
C256	0.165 (4)	0.0663 (19)	0.0535 (17)	−0.023 (2)	0.025 (2)	−0.0167 (15)
C257	0.116 (3)	0.0515 (15)	0.075 (2)	−0.0059 (16)	0.0346 (18)	−0.0122 (14)
C25B	0.0802 (17)	0.0389 (12)	0.0576 (14)	−0.0028 (11)	0.0119 (12)	−0.0022 (10)
C261	0.0474 (12)	0.0454 (12)	0.0622 (14)	−0.0030 (10)	−0.0060 (10)	0.0011 (10)
C262	0.0636 (15)	0.0569 (14)	0.0669 (16)	−0.0066 (12)	0.0022 (12)	0.0014 (12)
C263	0.0725 (18)	0.076 (2)	0.080 (2)	−0.0145 (15)	0.0040 (15)	0.0146 (16)
C264	0.0770 (19)	0.0629 (18)	0.107 (3)	−0.0158 (15)	−0.0132 (18)	0.0284 (17)
C265	0.083 (2)	0.0448 (14)	0.113 (3)	−0.0007 (13)	−0.0102 (19)	0.0030 (15)
C266	0.0616 (15)	0.0455 (13)	0.0822 (18)	0.0015 (11)	0.0001 (13)	−0.0013 (12)

Geometric parameters (Å, º)

S11—C17A	1.725 (2)	C164—C165	1.366 (5)
S11—C12	1.757 (3)	C164—H164	0.9300
C12—N13	1.293 (3)	C165—C166	1.384 (4)
C12—C127	1.505 (4)	C165—H165	0.9300
N13—N14	1.374 (3)	C166—H166	0.9300
N14—C17A	1.362 (3)	S21—C27A	1.728 (2)
N14—C15	1.380 (3)	S21—C22	1.755 (2)
C15—C16	1.379 (3)	C22—N23	1.296 (3)
C15—C151	1.492 (3)	C22—C227	1.504 (3)
C16—N17	1.401 (3)	N23—N24	1.372 (2)
C16—C161	1.471 (3)	N24—C27A	1.364 (3)
N17—C17A	1.314 (3)	N24—C25	1.381 (3)
C127—C121	1.506 (5)	C25—C26	1.376 (3)
C127—H12A	0.9700	C25—C251	1.494 (3)
C127—H12B	0.9700	C26—N27	1.403 (3)
C121—C122	1.373 (6)	C26—C261	1.473 (3)
C121—C126	1.392 (6)	N27—C27A	1.313 (3)
C122—C123	1.366 (6)	C227—C221	1.509 (4)
C122—H122	0.9300	C227—H27A	0.9700
C123—C124	1.368 (7)	C227—H27B	0.9700
C123—H123	0.9300	C221—C226	1.372 (4)
C124—C125	1.345 (10)	C221—C222	1.380 (4)
C124—Cl14	1.771 (5)	C222—C223	1.391 (4)
C125—C126	1.416 (8)	C222—H222	0.9300
C125—H125	0.9300	C223—C224	1.356 (5)
C126—H126	0.9300	C223—H223	0.9300
C131—C132	1.360 (9)	C224—C225	1.355 (5)
C131—C136	1.392 (8)	C224—Cl24	1.748 (3)
C132—C133	1.377 (8)	C225—C226	1.373 (4)
C132—H132	0.9300	C225—H225	0.9300
C133—C134	1.371 (11)	C226—H226	0.9300
C133—H133	0.9300	C251—C253	1.502 (3)
C134—C135	1.353 (13)	C251—H25A	0.9700
C134—Cl34	1.739 (8)	C251—H25B	0.9700
C135—C136	1.371 (10)	N251—C25B	1.370 (3)
C135—H135	0.9300	N251—C252	1.374 (3)
C136—H136	0.9300	N251—H251	0.83 (3)
C151—C153	1.503 (3)	C252—C253	1.358 (3)
C151—H15A	0.9700	C252—H252	0.9300
C151—H15B	0.9700	C253—C25A	1.432 (3)
N151—C15B	1.362 (4)	C25A—C254	1.397 (3)
N151—C152	1.368 (4)	C25A—C25B	1.411 (4)
N151—H151	0.82 (3)	C254—C255	1.377 (4)
C152—C153	1.355 (3)	C254—H254	0.9300
C152—H152	0.9300	C255—C256	1.380 (5)
C153—C15A	1.433 (3)	C255—H255	0.9300
C15A—C154	1.404 (4)	C256—C257	1.363 (5)
C15A—C15B	1.413 (4)	C256—H256	0.9300
C154—C155	1.368 (4)	C257—C25B	1.396 (4)
C154—H154	0.9300	C257—H257	0.9300
C155—C156	1.389 (6)	C261—C266	1.387 (3)
C155—H155	0.9300	C261—C262	1.390 (4)
C156—C157	1.372 (5)	C262—C263	1.382 (4)
C156—H156	0.9300	C262—H262	0.9300
C157—C15B	1.391 (4)	C263—C264	1.373 (5)
C157—H157	0.9300	C263—H263	0.9300
C161—C166	1.386 (4)	C264—C265	1.381 (5)
C161—C162	1.391 (4)	C264—H264	0.9300
C162—C163	1.382 (4)	C265—C266	1.386 (4)
C162—H162	0.9300	C265—H265	0.9300
C163—C164	1.367 (5)	C266—H266	0.9300
C163—H163	0.9300
C17A—S11—C12	87.89 (12)	C165—C164—H164	120.2
N13—C12—C127	121.8 (2)	C163—C164—H164	120.2
N13—C12—S11	116.85 (19)	C164—C165—C166	120.1 (3)
C127—C12—S11	121.3 (2)	C164—C165—H165	119.9
C12—N13—N14	107.92 (19)	C166—C165—H165	119.9
C17A—N14—N13	118.21 (18)	C165—C166—C161	121.2 (3)
C17A—N14—C15	108.51 (19)	C165—C166—H166	119.4
N13—N14—C15	133.20 (19)	C161—C166—H166	119.4
C16—C15—N14	103.65 (19)	C27A—S21—C22	88.11 (11)
C16—C15—C151	134.4 (2)	N23—C22—C227	122.2 (2)
N14—C15—C151	121.9 (2)	N23—C22—S21	116.74 (18)
C15—C16—N17	111.61 (19)	C227—C22—S21	121.03 (18)
C15—C16—C161	128.2 (2)	C22—N23—N24	107.96 (18)
N17—C16—C161	120.1 (2)	C27A—N24—N23	118.44 (18)
C17A—N17—C16	103.93 (18)	C27A—N24—C25	108.43 (18)
N17—C17A—N14	112.3 (2)	N23—N24—C25	133.07 (18)
N17—C17A—S11	138.63 (18)	C26—C25—N24	103.45 (18)
N14—C17A—S11	109.09 (17)	C26—C25—C251	133.4 (2)
C12—C127—C121	111.2 (9)	N24—C25—C251	122.88 (19)
C12—C127—H12A	109.4	C25—C26—N27	112.13 (19)
C121—C127—H12A	109.4	C25—C26—C261	127.6 (2)
C12—C127—H12B	109.4	N27—C26—C261	120.22 (19)
C121—C127—H12B	109.4	C27A—N27—C26	103.44 (17)
H12A—C127—H12B	108.0	N27—C27A—N24	112.5 (2)
C122—C121—C126	117.1 (4)	N27—C27A—S21	138.73 (17)
C122—C121—C127	116.4 (5)	N24—C27A—S21	108.72 (16)
C126—C121—C127	126.3 (5)	C22—C227—C221	114.2 (2)
C123—C122—C121	122.3 (5)	C22—C227—H27A	108.7
C123—C122—H122	118.8	C221—C227—H27A	108.7
C121—C122—H122	118.8	C22—C227—H27B	108.7
C122—C123—C124	119.4 (5)	C221—C227—H27B	108.7
C122—C123—H123	120.3	H27A—C227—H27B	107.6
C124—C123—H123	120.3	C226—C221—C222	117.8 (3)
C125—C124—C123	121.6 (6)	C226—C221—C227	122.1 (3)
C125—C124—Cl14	121.6 (5)	C222—C221—C227	120.2 (3)
C123—C124—Cl14	116.9 (5)	C221—C222—C223	120.7 (3)
C124—C125—C126	118.6 (6)	C221—C222—H222	119.6
C124—C125—H125	120.7	C223—C222—H222	119.6
C126—C125—H125	120.7	C224—C223—C222	119.2 (3)
C121—C126—C125	120.7 (6)	C224—C223—H223	120.4
C121—C126—H126	119.7	C222—C223—H223	120.4
C125—C126—H126	119.7	C225—C224—C223	121.3 (3)
C132—C131—C136	120.7 (9)	C225—C224—Cl24	119.9 (3)
C131—C132—C133	121.4 (8)	C223—C224—Cl24	118.9 (3)
C131—C132—H132	119.3	C224—C225—C226	119.2 (3)
C133—C132—H132	119.3	C224—C225—H225	120.4
C134—C133—C132	116.1 (8)	C226—C225—H225	120.4
C134—C133—H133	122.0	C221—C226—C225	121.8 (3)
C132—C133—H133	122.0	C221—C226—H226	119.1
C135—C134—C133	123.5 (8)	C225—C226—H226	119.1
C135—C134—Cl34	117.9 (9)	C25—C251—C253	115.17 (18)
C133—C134—Cl34	118.5 (8)	C25—C251—H25A	108.5
C134—C135—C136	119.9 (9)	C253—C251—H25A	108.5
C134—C135—H135	120.0	C25—C251—H25B	108.5
C136—C135—H135	120.0	C253—C251—H25B	108.5
C135—C136—C131	117.2 (9)	H25A—C251—H25B	107.5
C135—C136—H136	121.4	C25B—N251—C252	108.7 (2)
C131—C136—H136	121.4	C25B—N251—H251	129 (2)
C15—C151—C153	113.48 (19)	C252—N251—H251	123 (2)
C15—C151—H15A	108.9	C253—C252—N251	110.1 (2)
C153—C151—H15A	108.9	C253—C252—H252	124.9
C15—C151—H15B	108.9	N251—C252—H252	124.9
C153—C151—H15B	108.9	C252—C253—C25A	106.8 (2)
H15A—C151—H15B	107.7	C252—C253—C251	127.7 (2)
C15B—N151—C152	109.0 (2)	C25A—C253—C251	125.6 (2)
C15B—N151—H151	127 (2)	C254—C25A—C25B	119.0 (2)
C152—N151—H151	123 (2)	C254—C25A—C253	134.3 (2)
C153—C152—N151	110.6 (2)	C25B—C25A—C253	106.7 (2)
C153—C152—H152	124.7	C255—C254—C25A	118.6 (3)
N151—C152—H152	124.7	C255—C254—H254	120.7
C152—C153—C15A	106.1 (2)	C25A—C254—H254	120.7
C152—C153—C151	126.7 (2)	C254—C255—C256	121.6 (3)
C15A—C153—C151	127.2 (2)	C254—C255—H255	119.2
C154—C15A—C15B	118.9 (2)	C256—C255—H255	119.2
C154—C15A—C153	134.1 (3)	C257—C256—C255	121.5 (3)
C15B—C15A—C153	107.0 (2)	C257—C256—H256	119.3
C155—C154—C15A	118.8 (3)	C255—C256—H256	119.3
C155—C154—H154	120.6	C256—C257—C25B	118.1 (3)
C15A—C154—H154	120.6	C256—C257—H257	120.9
C154—C155—C156	121.5 (4)	C25B—C257—H257	120.9
C154—C155—H155	119.2	N251—C25B—C257	131.1 (3)
C156—C155—H155	119.2	N251—C25B—C25A	107.7 (2)
C157—C156—C155	121.5 (3)	C257—C25B—C25A	121.2 (3)
C157—C156—H156	119.3	C266—C261—C262	118.5 (2)
C155—C156—H156	119.3	C266—C261—C26	121.0 (2)
C156—C157—C15B	117.7 (3)	C262—C261—C26	120.4 (2)
C156—C157—H157	121.1	C263—C262—C261	120.7 (3)
C15B—C157—H157	121.1	C263—C262—H262	119.7
N151—C15B—C157	131.0 (3)	C261—C262—H262	119.7
N151—C15B—C15A	107.3 (2)	C264—C263—C262	120.5 (3)
C157—C15B—C15A	121.6 (3)	C264—C263—H263	119.7
C166—C161—C162	117.8 (2)	C262—C263—H263	119.7
C166—C161—C16	120.9 (2)	C263—C264—C265	119.4 (3)
C162—C161—C16	121.2 (2)	C263—C264—H264	120.3
C163—C162—C161	120.3 (3)	C265—C264—H264	120.3
C163—C162—H162	119.9	C264—C265—C266	120.4 (3)
C161—C162—H162	119.9	C264—C265—H265	119.8
C164—C163—C162	121.0 (3)	C266—C265—H265	119.8
C164—C163—H163	119.5	C265—C266—C261	120.5 (3)
C162—C163—H163	119.5	C265—C266—H266	119.8
C165—C164—C163	119.6 (3)	C261—C266—H266	119.8
C17A—S11—C12—N13	−1.1 (2)	C163—C164—C165—C166	−1.4 (5)
C17A—S11—C12—C127	178.2 (3)	C164—C165—C166—C161	1.4 (5)
C127—C12—N13—N14	−179.3 (3)	C162—C161—C166—C165	0.1 (4)
S11—C12—N13—N14	0.0 (3)	C16—C161—C166—C165	177.4 (2)
C12—N13—N14—C17A	1.5 (3)	C27A—S21—C22—N23	−0.6 (2)
C12—N13—N14—C15	177.8 (3)	C27A—S21—C22—C227	−177.5 (2)
C17A—N14—C15—C16	1.7 (2)	C227—C22—N23—N24	176.4 (2)
N13—N14—C15—C16	−174.9 (2)	S21—C22—N23—N24	−0.5 (3)
C17A—N14—C15—C151	−176.6 (2)	C22—N23—N24—C27A	1.7 (3)
N13—N14—C15—C151	6.9 (4)	C22—N23—N24—C25	178.6 (2)
N14—C15—C16—N17	−1.8 (2)	C27A—N24—C25—C26	1.5 (2)
C151—C15—C16—N17	176.1 (2)	N23—N24—C25—C26	−175.6 (2)
N14—C15—C16—C161	175.0 (2)	C27A—N24—C25—C251	−173.0 (2)
C151—C15—C16—C161	−7.1 (4)	N23—N24—C25—C251	9.9 (4)
C15—C16—N17—C17A	1.3 (3)	N24—C25—C26—N27	−1.4 (2)
C161—C16—N17—C17A	−175.9 (2)	C251—C25—C26—N27	172.2 (2)
C16—N17—C17A—N14	−0.2 (3)	N24—C25—C26—C261	175.8 (2)
C16—N17—C17A—S11	177.7 (2)	C251—C25—C26—C261	−10.6 (4)
N13—N14—C17A—N17	176.1 (2)	C25—C26—N27—C27A	0.8 (2)
C15—N14—C17A—N17	−1.0 (3)	C261—C26—N27—C27A	−176.7 (2)
N13—N14—C17A—S11	−2.4 (3)	C26—N27—C27A—N24	0.2 (3)
C15—N14—C17A—S11	−179.52 (16)	C26—N27—C27A—S21	178.2 (2)
C12—S11—C17A—N17	−176.1 (3)	N23—N24—C27A—N27	176.49 (19)
C12—S11—C17A—N14	1.82 (19)	C25—N24—C27A—N27	−1.1 (3)
N13—C12—C127—C121	175.2 (4)	N23—N24—C27A—S21	−2.1 (3)
S11—C12—C127—C121	−4.1 (6)	C25—N24—C27A—S21	−179.69 (15)
C12—C127—C121—C122	82.4 (18)	C22—S21—C27A—N27	−176.7 (3)
C12—C127—C121—C126	−103.3 (19)	C22—S21—C27A—N24	1.38 (18)
C126—C121—C122—C123	5 (3)	N23—C22—C227—C221	156.4 (3)
C127—C121—C122—C123	179.8 (11)	S21—C22—C227—C221	−26.9 (4)
C121—C122—C123—C124	−2.1 (17)	C22—C227—C221—C226	−69.1 (4)
C122—C123—C124—C125	0.9 (10)	C22—C227—C221—C222	111.2 (3)
C122—C123—C124—Cl14	179.1 (6)	C226—C221—C222—C223	−0.4 (4)
C123—C124—C125—C126	−2.8 (11)	C227—C221—C222—C223	179.3 (3)
Cl14—C124—C125—C126	179.1 (7)	C221—C222—C223—C224	1.2 (5)
C122—C121—C126—C125	−7 (3)	C222—C223—C224—C225	−1.1 (5)
C127—C121—C126—C125	178.9 (15)	C222—C223—C224—Cl24	179.0 (3)
C124—C125—C126—C121	5.8 (18)	C223—C224—C225—C226	0.4 (5)
C136—C131—C132—C133	−11 (5)	Cl24—C224—C225—C226	−179.8 (2)
C131—C132—C133—C134	2 (3)	C222—C221—C226—C225	−0.4 (4)
C132—C133—C134—C135	3 (2)	C227—C221—C226—C225	179.9 (3)
C132—C133—C134—Cl34	−175.7 (12)	C224—C225—C226—C221	0.4 (5)
C133—C134—C135—C136	0 (2)	C26—C25—C251—C253	103.2 (3)
Cl34—C134—C135—C136	178.8 (14)	N24—C25—C251—C253	−84.2 (3)
C134—C135—C136—C131	−8 (3)	C25B—N251—C252—C253	−0.5 (3)
C132—C131—C136—C135	13 (5)	N251—C252—C253—C25A	0.6 (3)
C16—C15—C151—C153	98.6 (3)	N251—C252—C253—C251	−179.1 (2)
N14—C15—C151—C153	−83.8 (3)	C25—C251—C253—C252	14.9 (3)
C15B—N151—C152—C153	−1.2 (3)	C25—C251—C253—C25A	−164.8 (2)
N151—C152—C153—C15A	1.1 (3)	C252—C253—C25A—C254	−179.0 (3)
N151—C152—C153—C151	−178.8 (2)	C251—C253—C25A—C254	0.7 (4)
C15—C151—C153—C152	21.5 (4)	C252—C253—C25A—C25B	−0.5 (3)
C15—C151—C153—C15A	−158.3 (2)	C251—C253—C25A—C25B	179.2 (2)
C152—C153—C15A—C154	179.7 (3)	C25B—C25A—C254—C255	−0.1 (4)
C151—C153—C15A—C154	−0.5 (5)	C253—C25A—C254—C255	178.3 (3)
C152—C153—C15A—C15B	−0.6 (3)	C25A—C254—C255—C256	0.6 (5)
C151—C153—C15A—C15B	179.3 (2)	C254—C255—C256—C257	−0.5 (5)
C15B—C15A—C154—C155	0.6 (5)	C255—C256—C257—C25B	−0.3 (5)
C153—C15A—C154—C155	−179.6 (3)	C252—N251—C25B—C257	179.8 (3)
C15A—C154—C155—C156	−0.6 (7)	C252—N251—C25B—C25A	0.1 (3)
C154—C155—C156—C157	−0.1 (8)	C256—C257—C25B—N251	−178.8 (3)
C155—C156—C157—C15B	0.8 (7)	C256—C257—C25B—C25A	0.8 (4)
C152—N151—C15B—C157	−179.6 (3)	C254—C25A—C25B—N251	179.0 (2)
C152—N151—C15B—C15A	0.8 (3)	C253—C25A—C25B—N251	0.2 (3)
C156—C157—C15B—N151	179.7 (4)	C254—C25A—C25B—C257	−0.6 (4)
C156—C157—C15B—C15A	−0.7 (6)	C253—C25A—C25B—C257	−179.4 (2)
C154—C15A—C15B—N151	179.7 (3)	C25—C26—C261—C266	148.9 (2)
C153—C15A—C15B—N151	−0.1 (3)	N27—C26—C261—C266	−34.0 (3)
C154—C15A—C15B—C157	0.0 (4)	C25—C26—C261—C262	−33.7 (3)
C153—C15A—C15B—C157	−179.8 (3)	N27—C26—C261—C262	143.4 (2)
C15—C16—C161—C166	158.1 (2)	C266—C261—C262—C263	−0.2 (4)
N17—C16—C161—C166	−25.3 (3)	C26—C261—C262—C263	−177.7 (2)
C15—C16—C161—C162	−24.7 (4)	C261—C262—C263—C264	0.8 (4)
N17—C16—C161—C162	151.9 (2)	C262—C263—C264—C265	−0.5 (5)
C166—C161—C162—C163	−1.6 (4)	C263—C264—C265—C266	−0.3 (5)
C16—C161—C162—C163	−178.9 (3)	C264—C265—C266—C261	0.9 (4)
C161—C162—C163—C164	1.7 (6)	C262—C261—C266—C265	−0.6 (4)
C162—C163—C164—C165	−0.2 (6)	C26—C261—C266—C265	176.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N151—H151···N17^i	0.83 (3)	2.11 (3)	2.912 (3)	162 (3)
N251—H251···N27^ii	0.83 (3)	2.27 (3)	3.087 (3)	167 (3)
C135—H135···Cg1^i	0.93	2.52	3.272 (11)	138
C225—H225···Cg2^ii	0.93	2.87	3.568 (4)	133
C252—H252···Cg3^ii	0.93	2.77	3.568 (3)	144

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+1/2.

2-(4-Chlorobenzyl)-6-(4-fluorophenyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole (II)

Crystal data

C26H18ClFN4S	F(000) = 976
Mr = 472.95	Dx = 1.370 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.340 (1) Å	Cell parameters from 5068 reflections
b = 11.1619 (7) Å	θ = 2.7–27.9°
c = 15.385 (1) Å	µ = 0.29 mm^−1
β = 119.48 (1)°	T = 296 K
V = 2293.2 (3) Å^3	Plate, yellow
Z = 4	0.46 × 0.44 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	5041 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3161 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −19→19
Tmin = 0.768, Tmax = 0.944	k = −13→13
16612 measured reflections	l = −18→19

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.9215P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
5041 reflections	Δρmax = 0.26 e Å^−3
323 parameters	Δρmin = −0.24 e Å^−3
23 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	Occ. (<1)
S1	0.29020 (4)	0.26704 (6)	0.45226 (5)	0.0598 (2)
C2	0.37289 (17)	0.1507 (2)	0.46549 (19)	0.0570 (6)
N3	0.46687 (13)	0.17314 (16)	0.51939 (14)	0.0535 (5)
N4	0.47701 (12)	0.28832 (15)	0.55296 (13)	0.0454 (4)
C5	0.55903 (15)	0.35639 (19)	0.61424 (15)	0.0451 (5)
C6	0.51834 (16)	0.46116 (19)	0.62492 (15)	0.0458 (5)
N7	0.41374 (13)	0.45963 (16)	0.57021 (13)	0.0491 (4)
C7A	0.39325 (15)	0.3533 (2)	0.52847 (16)	0.0474 (5)
C27	0.33592 (19)	0.0335 (2)	0.4129 (3)	0.0840 (9)	0.822 (6)
H27A	0.3797	−0.0295	0.4554	0.101*	0.822 (6)
H27B	0.3408	0.0348	0.3524	0.101*	0.822 (6)
C21	0.2299 (2)	0.0027 (3)	0.3856 (3)	0.0569 (7)	0.822 (6)
C22	0.1533 (3)	0.0360 (6)	0.2954 (3)	0.0736 (11)	0.822 (6)
H22	0.1666	0.0816	0.2526	0.088*	0.822 (6)
C23	0.0569 (3)	0.0035 (7)	0.2665 (4)	0.0869 (12)	0.822 (6)
H23	0.0054	0.0241	0.2034	0.104*	0.822 (6)
C24	0.0368 (3)	−0.0584 (5)	0.3295 (4)	0.0727 (12)	0.822 (6)
Cl24	−0.08535 (12)	−0.1013 (2)	0.2922 (3)	0.1368 (11)	0.822 (6)
C25	0.1119 (3)	−0.0917 (4)	0.4210 (4)	0.0811 (12)	0.822 (6)
H25	0.0979	−0.1344	0.4646	0.097*	0.822 (6)
C26	0.2088 (3)	−0.0614 (5)	0.4481 (3)	0.0722 (12)	0.822 (6)
H26	0.2607	−0.0851	0.5101	0.087*	0.822 (6)
C37	0.33592 (19)	0.0335 (2)	0.4129 (3)	0.0840 (9)	0.178 (6)
H37A	0.3766	−0.0300	0.4576	0.101*	0.178 (6)
H37B	0.3460	0.0324	0.3555	0.101*	0.178 (6)
C31	0.2272 (6)	0.0060 (10)	0.3779 (12)	0.0569 (7)	0.178 (6)
C32	0.1626 (10)	0.034 (3)	0.2808 (14)	0.0736 (11)	0.178 (6)
H32	0.1874	0.0604	0.2399	0.088*	0.178 (6)
C33	0.0623 (10)	0.023 (4)	0.2433 (17)	0.0869 (12)	0.178 (6)
H33	0.0184	0.0567	0.1819	0.104*	0.178 (6)
C34	0.0261 (9)	−0.037 (3)	0.2944 (16)	0.0727 (12)	0.178 (6)
Cl34	−0.1018 (5)	−0.0635 (9)	0.2309 (12)	0.1368 (11)	0.178 (6)
C35	0.0864 (11)	−0.060 (2)	0.3928 (15)	0.0811 (12)	0.178 (6)
H35	0.0603	−0.0899	0.4317	0.097*	0.178 (6)
C36	0.1883 (10)	−0.037 (3)	0.4342 (15)	0.0722 (12)	0.178 (6)
H36	0.2306	−0.0521	0.5017	0.087*	0.178 (6)
C51	0.66292 (15)	0.3124 (2)	0.65056 (16)	0.0490 (5)
H51A	0.7067	0.3806	0.6630	0.059*
H51B	0.6642	0.2643	0.5987	0.059*
N51	0.70786 (17)	0.11914 (19)	0.86245 (17)	0.0647 (6)
H51	0.685 (2)	0.074 (3)	0.892 (2)	0.078*
C52	0.64764 (17)	0.1730 (2)	0.77329 (18)	0.0552 (6)
H52	0.5783	0.1655	0.7375	0.066*
C53	0.70247 (15)	0.23931 (18)	0.74375 (16)	0.0454 (5)
C53A	0.80430 (16)	0.22541 (19)	0.81938 (17)	0.0505 (5)
C54	0.89531 (18)	0.2699 (2)	0.8328 (2)	0.0675 (7)
H54	0.8971	0.3208	0.7858	0.081*
C55	0.9821 (2)	0.2368 (3)	0.9171 (3)	0.0870 (10)
H55	1.0432	0.2662	0.9273	0.104*
C56	0.9801 (2)	0.1607 (3)	0.9869 (3)	0.0915 (10)
H56	1.0401	0.1393	1.0428	0.110*
C57	0.8927 (2)	0.1159 (3)	0.9764 (2)	0.0808 (9)
H57	0.8923	0.0648	1.0240	0.097*
C57A	0.80467 (18)	0.1494 (2)	0.89221 (18)	0.0581 (6)
C61	0.57262 (17)	0.56426 (19)	0.68713 (17)	0.0488 (5)
C62	0.66559 (18)	0.5491 (2)	0.77200 (18)	0.0600 (6)
H62	0.6919	0.4723	0.7906	0.072*
C63	0.7196 (2)	0.6456 (2)	0.8292 (2)	0.0684 (7)
H63	0.7823	0.6348	0.8851	0.082*
C64	0.6791 (2)	0.7564 (2)	0.8021 (2)	0.0660 (7)
F64	0.73381 (13)	0.85184 (14)	0.85653 (14)	0.0915 (5)
C65	0.5862 (2)	0.7756 (2)	0.7227 (2)	0.0687 (7)
H65	0.5588	0.8522	0.7080	0.082*
C66	0.53332 (19)	0.6786 (2)	0.66408 (19)	0.0582 (6)
H66	0.4706	0.6907	0.6086	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0409 (3)	0.0612 (4)	0.0683 (4)	0.0045 (3)	0.0199 (3)	−0.0128 (3)
C2	0.0489 (13)	0.0515 (13)	0.0685 (15)	0.0016 (10)	0.0272 (12)	−0.0117 (12)
N3	0.0446 (10)	0.0464 (11)	0.0648 (12)	0.0021 (8)	0.0234 (9)	−0.0089 (9)
N4	0.0415 (9)	0.0444 (10)	0.0483 (10)	0.0047 (8)	0.0205 (8)	−0.0039 (8)
C5	0.0462 (11)	0.0457 (12)	0.0417 (11)	0.0006 (9)	0.0202 (10)	0.0016 (9)
C6	0.0496 (12)	0.0450 (12)	0.0434 (12)	0.0024 (10)	0.0233 (10)	0.0029 (10)
N7	0.0499 (11)	0.0460 (11)	0.0505 (11)	0.0056 (8)	0.0241 (9)	−0.0014 (9)
C7A	0.0436 (11)	0.0510 (13)	0.0463 (12)	0.0066 (10)	0.0211 (10)	−0.0002 (10)
C27	0.0577 (16)	0.0643 (17)	0.127 (3)	−0.0081 (13)	0.0428 (17)	−0.0350 (17)
C21	0.0526 (14)	0.0478 (13)	0.0664 (17)	−0.0039 (11)	0.0264 (13)	−0.0159 (12)
C22	0.0705 (19)	0.100 (2)	0.057 (2)	−0.0097 (18)	0.0358 (16)	0.0005 (19)
C23	0.069 (2)	0.107 (4)	0.056 (3)	−0.004 (2)	0.0089 (18)	0.001 (2)
C24	0.0492 (17)	0.064 (3)	0.097 (4)	−0.0151 (18)	0.030 (2)	−0.018 (3)
Cl24	0.0644 (7)	0.1099 (12)	0.221 (3)	−0.0290 (7)	0.0590 (12)	−0.0207 (14)
C25	0.090 (3)	0.066 (3)	0.099 (3)	−0.005 (2)	0.056 (3)	0.020 (2)
C26	0.068 (2)	0.064 (3)	0.064 (2)	0.008 (2)	0.0168 (18)	0.0131 (16)
C37	0.0577 (16)	0.0643 (17)	0.127 (3)	−0.0081 (13)	0.0428 (17)	−0.0350 (17)
C31	0.0526 (14)	0.0478 (13)	0.0664 (17)	−0.0039 (11)	0.0264 (13)	−0.0159 (12)
C32	0.0705 (19)	0.100 (2)	0.057 (2)	−0.0097 (18)	0.0358 (16)	0.0005 (19)
C33	0.069 (2)	0.107 (4)	0.056 (3)	−0.004 (2)	0.0089 (18)	0.001 (2)
C34	0.0492 (17)	0.064 (3)	0.097 (4)	−0.0151 (18)	0.030 (2)	−0.018 (3)
Cl34	0.0644 (7)	0.1099 (12)	0.221 (3)	−0.0290 (7)	0.0590 (12)	−0.0207 (14)
C35	0.090 (3)	0.066 (3)	0.099 (3)	−0.005 (2)	0.056 (3)	0.020 (2)
C36	0.068 (2)	0.064 (3)	0.064 (2)	0.008 (2)	0.0168 (18)	0.0131 (16)
C51	0.0426 (11)	0.0523 (13)	0.0526 (13)	−0.0012 (10)	0.0237 (10)	−0.0027 (10)
N51	0.0671 (14)	0.0548 (13)	0.0692 (14)	−0.0010 (10)	0.0313 (12)	0.0142 (11)
C52	0.0492 (13)	0.0519 (13)	0.0596 (15)	−0.0005 (11)	0.0230 (12)	0.0035 (11)
C53	0.0407 (11)	0.0408 (12)	0.0533 (13)	0.0018 (9)	0.0221 (10)	−0.0020 (10)
C53A	0.0463 (12)	0.0391 (12)	0.0608 (14)	0.0049 (9)	0.0223 (11)	−0.0029 (11)
C54	0.0469 (13)	0.0648 (16)	0.0834 (18)	−0.0001 (12)	0.0265 (13)	−0.0016 (14)
C55	0.0450 (14)	0.086 (2)	0.108 (3)	0.0014 (14)	0.0204 (16)	−0.011 (2)
C56	0.0654 (19)	0.078 (2)	0.088 (2)	0.0222 (16)	0.0051 (17)	0.0004 (18)
C57	0.078 (2)	0.0622 (17)	0.0742 (19)	0.0153 (15)	0.0164 (16)	0.0118 (14)
C57A	0.0590 (15)	0.0406 (13)	0.0632 (15)	0.0081 (11)	0.0213 (12)	0.0019 (11)
C61	0.0595 (14)	0.0441 (12)	0.0518 (13)	−0.0012 (10)	0.0343 (12)	−0.0004 (10)
C62	0.0647 (15)	0.0517 (14)	0.0577 (14)	−0.0010 (12)	0.0255 (13)	−0.0039 (12)
C63	0.0678 (16)	0.0641 (17)	0.0685 (17)	−0.0094 (13)	0.0298 (14)	−0.0132 (14)
C64	0.0787 (18)	0.0556 (16)	0.0814 (18)	−0.0219 (14)	0.0530 (16)	−0.0191 (14)
F64	0.1081 (13)	0.0656 (10)	0.1202 (14)	−0.0371 (9)	0.0711 (11)	−0.0366 (9)
C65	0.089 (2)	0.0401 (13)	0.098 (2)	−0.0016 (13)	0.0619 (18)	−0.0014 (14)
C66	0.0650 (15)	0.0508 (14)	0.0680 (16)	0.0028 (11)	0.0399 (13)	0.0035 (12)

Geometric parameters (Å, º)

S1—C7A	1.725 (2)	C35—C36	1.390 (9)
S1—C2	1.756 (2)	C35—H35	0.9300
C2—N3	1.285 (3)	C36—H36	0.9300
C2—C27	1.495 (3)	C51—C53	1.494 (3)
N3—N4	1.365 (2)	C51—H51A	0.9700
N4—C7A	1.357 (3)	C51—H51B	0.9700
N4—C5	1.372 (3)	N51—C52	1.360 (3)
C5—C6	1.373 (3)	N51—C57A	1.364 (3)
C5—C51	1.489 (3)	N51—H51	0.86 (3)
C6—N7	1.398 (3)	C52—C53	1.355 (3)
C6—C61	1.466 (3)	C52—H52	0.9300
N7—C7A	1.312 (3)	C53—C53A	1.424 (3)
C27—C21	1.506 (4)	C53A—C54	1.398 (3)
C27—H27A	0.9700	C53A—C57A	1.403 (3)
C27—H27B	0.9700	C54—C55	1.376 (4)
C21—C22	1.356 (4)	C54—H54	0.9300
C21—C26	1.359 (4)	C55—C56	1.383 (5)
C22—C23	1.368 (5)	C55—H55	0.9300
C22—H22	0.9300	C56—C57	1.363 (4)
C23—C24	1.343 (5)	C56—H56	0.9300
C23—H23	0.9300	C57—C57A	1.386 (3)
C24—C25	1.361 (5)	C57—H57	0.9300
C24—Cl24	1.735 (3)	C61—C66	1.381 (3)
C25—C26	1.374 (5)	C61—C62	1.391 (3)
C25—H25	0.9300	C62—C63	1.380 (3)
C26—H26	0.9300	C62—H62	0.9300
C31—C36	1.360 (9)	C63—C64	1.355 (4)
C31—C32	1.361 (9)	C63—H63	0.9300
C32—C33	1.358 (9)	C64—F64	1.360 (3)
C32—H32	0.9300	C64—C65	1.363 (4)
C33—C34	1.343 (10)	C65—C66	1.387 (3)
C33—H33	0.9300	C65—H65	0.9300
C34—C35	1.353 (10)	C66—H66	0.9300
C34—Cl34	1.733 (8)
C7A—S1—C2	88.03 (11)	C31—C36—C35	121.3 (11)
N3—C2—C27	121.7 (2)	C31—C36—H36	119.3
N3—C2—S1	116.61 (17)	C35—C36—H36	119.3
C27—C2—S1	121.61 (18)	C5—C51—C53	113.22 (18)
C2—N3—N4	108.07 (17)	C5—C51—H51A	108.9
C7A—N4—N3	118.80 (17)	C53—C51—H51A	108.9
C7A—N4—C5	108.52 (17)	C5—C51—H51B	108.9
N3—N4—C5	132.59 (17)	C53—C51—H51B	108.9
N4—C5—C6	103.70 (18)	H51A—C51—H51B	107.7
N4—C5—C51	121.71 (19)	C52—N51—C57A	108.4 (2)
C6—C5—C51	134.6 (2)	C52—N51—H51	123.0 (18)
C5—C6—N7	111.86 (18)	C57A—N51—H51	128.6 (18)
C5—C6—C61	126.9 (2)	C53—C52—N51	110.7 (2)
N7—C6—C61	121.16 (19)	C53—C52—H52	124.6
C7A—N7—C6	103.48 (17)	N51—C52—H52	124.6
N7—C7A—N4	112.42 (18)	C52—C53—C53A	106.2 (2)
N7—C7A—S1	139.12 (17)	C52—C53—C51	126.42 (19)
N4—C7A—S1	108.44 (15)	C53A—C53—C51	127.4 (2)
C2—C27—C21	114.9 (2)	C54—C53A—C57A	119.1 (2)
C2—C27—H27A	108.5	C54—C53A—C53	134.1 (2)
C21—C27—H27A	108.5	C57A—C53A—C53	106.9 (2)
C2—C27—H27B	108.5	C55—C54—C53A	118.4 (3)
C21—C27—H27B	108.5	C55—C54—H54	120.8
H27A—C27—H27B	107.5	C53A—C54—H54	120.8
C22—C21—C26	118.8 (3)	C54—C55—C56	121.1 (3)
C22—C21—C27	119.7 (3)	C54—C55—H55	119.5
C26—C21—C27	121.5 (3)	C56—C55—H55	119.5
C21—C22—C23	120.8 (4)	C57—C56—C55	122.0 (3)
C21—C22—H22	119.6	C57—C56—H56	119.0
C23—C22—H22	119.6	C55—C56—H56	119.0
C24—C23—C22	119.9 (3)	C56—C57—C57A	117.4 (3)
C24—C23—H23	120.0	C56—C57—H57	121.3
C22—C23—H23	120.0	C57A—C57—H57	121.3
C23—C24—C25	120.5 (3)	N51—C57A—C57	130.3 (3)
C23—C24—Cl24	119.8 (3)	N51—C57A—C53A	107.8 (2)
C25—C24—Cl24	119.6 (3)	C57—C57A—C53A	121.9 (3)
C24—C25—C26	119.0 (3)	C66—C61—C62	118.0 (2)
C24—C25—H25	120.5	C66—C61—C6	121.5 (2)
C26—C25—H25	120.5	C62—C61—C6	120.5 (2)
C21—C26—C25	120.9 (3)	C63—C62—C61	121.4 (2)
C21—C26—H26	119.6	C63—C62—H62	119.3
C25—C26—H26	119.6	C61—C62—H62	119.3
C36—C31—C32	118.0 (9)	C64—C63—C62	118.4 (3)
C33—C32—C31	120.4 (11)	C64—C63—H63	120.8
C33—C32—H32	119.8	C62—C63—H63	120.8
C31—C32—H32	119.8	C63—C64—F64	118.4 (3)
C34—C33—C32	120.4 (12)	C63—C64—C65	122.6 (2)
C34—C33—H33	119.8	F64—C64—C65	119.0 (2)
C32—C33—H33	119.8	C64—C65—C66	118.6 (2)
C33—C34—C35	119.7 (10)	C64—C65—H65	120.7
C33—C34—Cl34	115.7 (11)	C66—C65—H65	120.7
C35—C34—Cl34	124.1 (11)	C61—C66—C65	120.9 (2)
C34—C35—C36	118.3 (11)	C61—C66—H66	119.6
C34—C35—H35	120.8	C65—C66—H66	119.6
C36—C35—H35	120.8
C7A—S1—C2—N3	−0.8 (2)	C33—C34—C35—C36	−10 (5)
C7A—S1—C2—C27	−178.1 (3)	Cl34—C34—C35—C36	179 (2)
C27—C2—N3—N4	176.9 (2)	C32—C31—C36—C35	4 (3)
S1—C2—N3—N4	−0.4 (3)	C34—C35—C36—C31	0 (4)
C2—N3—N4—C7A	1.9 (3)	N4—C5—C51—C53	−86.5 (2)
C2—N3—N4—C5	178.1 (2)	C6—C5—C51—C53	95.9 (3)
C7A—N4—C5—C6	1.1 (2)	C57A—N51—C52—C53	−0.6 (3)
N3—N4—C5—C6	−175.4 (2)	N51—C52—C53—C53A	0.4 (3)
C7A—N4—C5—C51	−177.14 (19)	N51—C52—C53—C51	−179.3 (2)
N3—N4—C5—C51	6.3 (4)	C5—C51—C53—C52	27.7 (3)
N4—C5—C6—N7	−1.2 (2)	C5—C51—C53—C53A	−151.9 (2)
C51—C5—C6—N7	176.8 (2)	C52—C53—C53A—C54	−180.0 (3)
N4—C5—C6—C61	176.9 (2)	C51—C53—C53A—C54	−0.3 (4)
C51—C5—C6—C61	−5.2 (4)	C52—C53—C53A—C57A	−0.1 (2)
C5—C6—N7—C7A	0.7 (2)	C51—C53—C53A—C57A	179.6 (2)
C61—C6—N7—C7A	−177.5 (2)	C57A—C53A—C54—C55	0.3 (4)
C6—N7—C7A—N4	0.0 (2)	C53—C53A—C54—C55	−179.8 (2)
C6—N7—C7A—S1	178.2 (2)	C53A—C54—C55—C56	0.4 (4)
N3—N4—C7A—N7	176.32 (19)	C54—C55—C56—C57	−0.7 (5)
C5—N4—C7A—N7	−0.8 (3)	C55—C56—C57—C57A	0.1 (5)
N3—N4—C7A—S1	−2.4 (2)	C52—N51—C57A—C57	−178.9 (3)
C5—N4—C7A—S1	−179.50 (14)	C52—N51—C57A—C53A	0.5 (3)
C2—S1—C7A—N7	−176.6 (3)	C56—C57—C57A—N51	180.0 (3)
C2—S1—C7A—N4	1.65 (17)	C56—C57—C57A—C53A	0.7 (4)
N3—C2—C27—C21	158.5 (3)	C54—C53A—C57A—N51	179.7 (2)
S1—C2—C27—C21	−24.3 (4)	C53—C53A—C57A—N51	−0.2 (3)
C2—C27—C21—C22	90.8 (5)	C54—C53A—C57A—C57	−0.9 (4)
C2—C27—C21—C26	−91.3 (5)	C53—C53A—C57A—C57	179.2 (2)
C26—C21—C22—C23	−1.6 (7)	C5—C6—C61—C66	153.4 (2)
C27—C21—C22—C23	176.4 (5)	N7—C6—C61—C66	−28.7 (3)
C21—C22—C23—C24	2.6 (9)	C5—C6—C61—C62	−27.0 (4)
C22—C23—C24—C25	−1.6 (10)	N7—C6—C61—C62	150.8 (2)
C22—C23—C24—Cl24	−179.2 (5)	C66—C61—C62—C63	−3.0 (4)
C23—C24—C25—C26	−0.2 (9)	C6—C61—C62—C63	177.3 (2)
Cl24—C24—C25—C26	177.4 (4)	C61—C62—C63—C64	1.3 (4)
C22—C21—C26—C25	−0.3 (7)	C62—C63—C64—F64	−177.8 (2)
C27—C21—C26—C25	−178.2 (4)	C62—C63—C64—C65	2.1 (4)
C24—C25—C26—C21	1.1 (8)	C63—C64—C65—C66	−3.6 (4)
C36—C31—C32—C33	3 (3)	F64—C64—C65—C66	176.3 (2)
C31—C32—C33—C34	−13 (5)	C62—C61—C66—C65	1.5 (3)
C32—C33—C34—C35	17 (6)	C6—C61—C66—C65	−178.9 (2)
C32—C33—C34—Cl34	−171 (2)	C64—C65—C66—C61	1.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···N7^i	0.86 (3)	2.27 (3)	3.102 (3)	165 (3)
C25—H25···Cg1^i	0.93	2.75	3.637 (5)	161
C35—H35···Cg1^i	0.93	3.32	4.062 (5)	139

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

6-(4-Bromophenyl)-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole (III)

Crystal data

C26H18BrClN4S	Dx = 1.491 Mg m^−3
Mr = 533.85	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4645 reflections
a = 9.5735 (8) Å	θ = 2.6–27.9°
b = 9.6860 (9) Å	µ = 1.95 mm^−1
c = 25.644 (2) Å	T = 296 K
V = 2377.9 (4) Å^3	Block, yellow
Z = 4	0.48 × 0.44 × 0.44 mm
F(000) = 1080

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	4645 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3140 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 27.9°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→12
Tmin = 0.368, Tmax = 0.424	k = −11→12
10501 measured reflections	l = −32→27

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.2472P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.40 e Å^−3
4645 reflections	Δρmin = −0.51 e Å^−3
323 parameters	Absolute structure: Flack x determined using 943 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
18 restraints	Absolute structure parameter: 0.014 (5)
Primary atom site location: difference Fourier map

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	Occ. (<1)
S1	0.83700 (15)	0.41040 (12)	0.58869 (4)	0.0607 (4)
C2	0.8115 (5)	0.5817 (5)	0.60822 (16)	0.0521 (11)
N3	0.7295 (4)	0.6558 (4)	0.58024 (14)	0.0484 (9)
N4	0.6814 (4)	0.5756 (3)	0.53971 (12)	0.0420 (8)
C5	0.5916 (4)	0.5991 (4)	0.49850 (14)	0.0398 (9)
C6	0.5915 (5)	0.4749 (4)	0.47243 (16)	0.0421 (10)
N7	0.6775 (4)	0.3777 (3)	0.49620 (12)	0.0463 (8)
C7A	0.7273 (5)	0.4426 (4)	0.53667 (16)	0.0442 (11)
C27	0.8805 (6)	0.6365 (6)	0.65587 (17)	0.0659 (14)	0.839 (5)
H27A	0.8988	0.7342	0.6512	0.079*	0.839 (5)
H27B	0.9695	0.5903	0.6606	0.079*	0.839 (5)
C21	0.792 (3)	0.6161 (7)	0.7041 (7)	0.0583 (16)	0.839 (5)
C22	0.8012 (8)	0.4946 (7)	0.7315 (2)	0.072 (2)	0.839 (5)
H22	0.8610	0.4253	0.7201	0.086*	0.839 (5)
C23	0.7217 (8)	0.4742 (8)	0.7761 (2)	0.078 (2)	0.839 (5)
H23	0.7263	0.3912	0.7942	0.094*	0.839 (5)
C24	0.6363 (7)	0.5786 (10)	0.7928 (3)	0.072 (2)	0.839 (5)
Cl24	0.5446 (3)	0.5544 (4)	0.85097 (8)	0.1052 (12)	0.839 (5)
C25	0.6247 (11)	0.6984 (10)	0.7669 (4)	0.093 (3)	0.839 (5)
H25	0.5661	0.7679	0.7790	0.111*	0.839 (5)
C26	0.7030 (9)	0.7164 (8)	0.7212 (4)	0.081 (3)	0.839 (5)
H26	0.6940	0.7978	0.7023	0.097*	0.839 (5)
C37	0.8805 (6)	0.6365 (6)	0.65587 (17)	0.0659 (14)	0.161 (5)
H37A	0.9104	0.7306	0.6494	0.079*	0.161 (5)
H37B	0.9631	0.5818	0.6632	0.079*	0.161 (5)
C31	0.786 (13)	0.635 (3)	0.703 (4)	0.0583 (16)	0.161 (5)
C32	0.733 (4)	0.515 (3)	0.7245 (12)	0.072 (2)	0.161 (5)
H32	0.7558	0.4307	0.7096	0.086*	0.161 (5)
C33	0.646 (4)	0.519 (3)	0.7682 (12)	0.078 (2)	0.161 (5)
H33	0.6213	0.4386	0.7853	0.094*	0.161 (5)
C34	0.599 (6)	0.645 (3)	0.7853 (16)	0.072 (2)	0.161 (5)
Cl34	0.4934 (14)	0.653 (2)	0.8408 (5)	0.1052 (12)	0.161 (5)
C35	0.644 (6)	0.763 (3)	0.7640 (19)	0.093 (3)	0.161 (5)
H35	0.6135	0.8473	0.7768	0.111*	0.161 (5)
C36	0.739 (6)	0.758 (3)	0.7223 (18)	0.081 (3)	0.161 (5)
H36	0.7694	0.8398	0.7074	0.097*	0.161 (5)
C51	0.5177 (5)	0.7330 (4)	0.49086 (18)	0.0491 (11)
H51A	0.4648	0.7523	0.5223	0.059*
H51B	0.4508	0.7209	0.4628	0.059*
N51	0.6774 (5)	1.0775 (4)	0.47897 (15)	0.0592 (10)
H51	0.669 (5)	1.175 (5)	0.4903 (17)	0.071*
C52	0.5912 (5)	0.9832 (5)	0.50168 (18)	0.0517 (11)
H52	0.5316	1.0024	0.5294	0.062*
C53	0.6035 (4)	0.8576 (4)	0.47868 (16)	0.0441 (11)
C53A	0.7043 (5)	0.8739 (5)	0.43823 (15)	0.0455 (10)
C54	0.7624 (5)	0.7861 (5)	0.40072 (18)	0.0572 (12)
H54	0.7335	0.6946	0.3982	0.069*
C55	0.8628 (6)	0.8371 (6)	0.3677 (2)	0.0751 (16)
H55	0.9015	0.7791	0.3427	0.090*
C56	0.9083 (7)	0.9735 (7)	0.3707 (2)	0.0797 (18)
H56	0.9777	1.0046	0.3482	0.096*
C57	0.8518 (6)	1.0620 (6)	0.4065 (2)	0.0687 (15)
H57	0.8813	1.1534	0.4084	0.082*
C57A	0.7497 (5)	1.0127 (5)	0.43978 (18)	0.0523 (12)
C61	0.5199 (4)	0.4425 (4)	0.42318 (15)	0.0407 (10)
C62	0.3870 (5)	0.4889 (5)	0.41314 (17)	0.0540 (12)
H62	0.3377	0.5345	0.4392	0.065*
C63	0.3253 (5)	0.4693 (5)	0.36521 (18)	0.0591 (13)
H63	0.2361	0.5032	0.3587	0.071*
C64	0.3972 (5)	0.3988 (6)	0.32711 (16)	0.0573 (13)
Br64	0.31651 (7)	0.38367 (7)	0.25942 (2)	0.0898 (3)
C65	0.5256 (5)	0.3449 (5)	0.33654 (17)	0.0593 (13)
H65	0.5717	0.2937	0.3111	0.071*
C66	0.5865 (5)	0.3678 (5)	0.38478 (16)	0.0524 (12)
H66	0.6748	0.3318	0.3914	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0771 (8)	0.0558 (7)	0.0490 (6)	0.0067 (8)	−0.0131 (6)	0.0130 (6)
C2	0.057 (3)	0.061 (3)	0.038 (2)	−0.007 (3)	−0.001 (2)	0.007 (2)
N3	0.059 (2)	0.046 (2)	0.0407 (19)	−0.0101 (19)	−0.0035 (18)	0.0027 (17)
N4	0.055 (2)	0.034 (2)	0.0360 (17)	0.000 (2)	−0.0029 (17)	0.0021 (14)
C5	0.046 (2)	0.037 (2)	0.037 (2)	−0.003 (2)	−0.0002 (19)	0.009 (2)
C6	0.046 (2)	0.037 (3)	0.043 (2)	−0.007 (2)	0.004 (2)	0.003 (2)
N7	0.062 (2)	0.0325 (18)	0.0440 (18)	0.004 (2)	−0.0054 (19)	0.0006 (16)
C7A	0.057 (3)	0.036 (3)	0.040 (2)	0.001 (2)	−0.002 (2)	0.0116 (19)
C27	0.072 (3)	0.080 (4)	0.046 (3)	−0.021 (3)	−0.007 (2)	0.004 (3)
C21	0.070 (4)	0.064 (4)	0.041 (2)	−0.015 (5)	−0.016 (3)	−0.004 (4)
C22	0.088 (6)	0.061 (4)	0.066 (4)	−0.002 (4)	0.020 (4)	0.001 (3)
C23	0.095 (6)	0.074 (5)	0.066 (4)	−0.011 (4)	0.019 (4)	0.006 (4)
C24	0.057 (5)	0.103 (7)	0.056 (4)	−0.020 (5)	0.005 (3)	−0.017 (4)
Cl24	0.0763 (14)	0.165 (3)	0.0743 (12)	−0.0284 (17)	0.0220 (11)	−0.0164 (15)
C25	0.086 (6)	0.113 (7)	0.079 (5)	0.017 (8)	0.001 (4)	−0.012 (7)
C26	0.091 (7)	0.083 (5)	0.070 (4)	0.008 (5)	−0.010 (4)	0.008 (4)
C37	0.072 (3)	0.080 (4)	0.046 (3)	−0.021 (3)	−0.007 (2)	0.004 (3)
C31	0.070 (4)	0.064 (4)	0.041 (2)	−0.015 (5)	−0.016 (3)	−0.004 (4)
C32	0.088 (6)	0.061 (4)	0.066 (4)	−0.002 (4)	0.020 (4)	0.001 (3)
C33	0.095 (6)	0.074 (5)	0.066 (4)	−0.011 (4)	0.019 (4)	0.006 (4)
C34	0.057 (5)	0.103 (7)	0.056 (4)	−0.020 (5)	0.005 (3)	−0.017 (4)
Cl34	0.0763 (14)	0.165 (3)	0.0743 (12)	−0.0284 (17)	0.0220 (11)	−0.0164 (15)
C35	0.086 (6)	0.113 (7)	0.079 (5)	0.017 (8)	0.001 (4)	−0.012 (7)
C36	0.091 (7)	0.083 (5)	0.070 (4)	0.008 (5)	−0.010 (4)	0.008 (4)
C51	0.052 (3)	0.042 (3)	0.053 (3)	0.004 (2)	−0.006 (2)	0.001 (2)
N51	0.079 (3)	0.038 (2)	0.060 (2)	0.008 (3)	−0.017 (2)	−0.001 (2)
C52	0.061 (3)	0.044 (3)	0.050 (3)	0.008 (3)	−0.006 (2)	0.000 (2)
C53	0.051 (2)	0.040 (3)	0.041 (2)	0.007 (2)	−0.015 (2)	0.004 (2)
C53A	0.055 (3)	0.039 (2)	0.042 (2)	0.004 (2)	−0.010 (2)	0.005 (2)
C54	0.065 (3)	0.055 (3)	0.051 (3)	0.003 (3)	−0.006 (2)	0.004 (3)
C55	0.083 (4)	0.083 (4)	0.060 (3)	0.009 (4)	0.004 (3)	0.002 (3)
C56	0.076 (4)	0.087 (5)	0.076 (4)	0.001 (4)	0.005 (3)	0.027 (4)
C57	0.073 (4)	0.051 (3)	0.082 (4)	−0.005 (3)	−0.006 (3)	0.026 (3)
C57A	0.062 (3)	0.039 (3)	0.057 (3)	−0.001 (2)	−0.016 (2)	0.011 (2)
C61	0.042 (2)	0.042 (3)	0.038 (2)	−0.013 (2)	0.0017 (19)	0.0045 (19)
C62	0.053 (3)	0.063 (3)	0.047 (3)	−0.010 (3)	0.006 (2)	−0.004 (2)
C63	0.045 (3)	0.074 (3)	0.058 (3)	−0.004 (3)	−0.005 (3)	−0.003 (3)
C64	0.059 (3)	0.072 (3)	0.040 (2)	−0.019 (3)	−0.008 (2)	−0.003 (3)
Br64	0.0976 (4)	0.1173 (5)	0.0545 (3)	−0.0123 (4)	−0.0222 (3)	−0.0103 (3)
C65	0.064 (3)	0.072 (4)	0.042 (2)	−0.008 (3)	0.001 (2)	−0.012 (2)
C66	0.050 (3)	0.058 (3)	0.049 (2)	−0.002 (3)	0.001 (2)	0.004 (2)

Geometric parameters (Å, º)

S1—C7A	1.726 (4)	C35—C36	1.399 (14)
S1—C2	1.750 (5)	C35—H35	0.9300
C2—N3	1.283 (5)	C36—H36	0.9300
C2—C27	1.487 (6)	C51—C53	1.493 (6)
N3—N4	1.376 (5)	C51—H51A	0.9700
N4—C7A	1.363 (5)	C51—H51B	0.9700
N4—C5	1.381 (5)	N51—C52	1.362 (6)
C5—C6	1.376 (6)	N51—C57A	1.373 (6)
C5—C51	1.490 (6)	N51—H51	0.99 (5)
C6—N7	1.391 (5)	C52—C53	1.357 (6)
C6—C61	1.471 (6)	C52—H52	0.9300
N7—C7A	1.304 (5)	C53—C53A	1.426 (6)
C27—C21	1.511 (7)	C53A—C54	1.400 (6)
C27—H27A	0.9700	C53A—C57A	1.413 (7)
C27—H27B	0.9700	C54—C55	1.373 (7)
C21—C26	1.367 (11)	C54—H54	0.9300
C21—C22	1.373 (12)	C55—C56	1.393 (8)
C22—C23	1.387 (8)	C55—H55	0.9300
C22—H22	0.9300	C56—C57	1.367 (8)
C23—C24	1.369 (11)	C56—H56	0.9300
C23—H23	0.9300	C57—C57A	1.383 (7)
C24—C25	1.341 (11)	C57—H57	0.9300
C24—Cl24	1.746 (6)	C61—C62	1.374 (6)
C25—C26	1.402 (10)	C61—C66	1.378 (6)
C25—H25	0.9300	C62—C63	1.377 (6)
C26—H26	0.9300	C62—H62	0.9300
C31—C36	1.369 (14)	C63—C64	1.376 (7)
C31—C32	1.373 (17)	C63—H63	0.9300
C32—C33	1.395 (13)	C64—C65	1.358 (7)
C32—H32	0.9300	C64—Br64	1.906 (4)
C33—C34	1.368 (16)	C65—C66	1.385 (6)
C33—H33	0.9300	C65—H65	0.9300
C34—C35	1.340 (16)	C66—H66	0.9300
C34—Cl34	1.746 (12)
C7A—S1—C2	88.0 (2)	C31—C36—C35	121.1 (16)
N3—C2—C27	122.1 (5)	C31—C36—H36	119.4
N3—C2—S1	117.1 (3)	C35—C36—H36	119.4
C27—C2—S1	120.8 (4)	C5—C51—C53	118.0 (3)
C2—N3—N4	108.1 (4)	C5—C51—H51A	107.8
C7A—N4—N3	117.9 (3)	C53—C51—H51A	107.8
C7A—N4—C5	108.2 (3)	C5—C51—H51B	107.8
N3—N4—C5	133.9 (3)	C53—C51—H51B	107.8
C6—C5—N4	103.2 (3)	H51A—C51—H51B	107.1
C6—C5—C51	134.1 (4)	C52—N51—C57A	108.2 (4)
N4—C5—C51	122.7 (4)	C52—N51—H51	117 (3)
C5—C6—N7	112.2 (4)	C57A—N51—H51	134 (3)
C5—C6—C61	127.2 (4)	C53—C52—N51	111.3 (4)
N7—C6—C61	120.5 (4)	C53—C52—H52	124.4
C7A—N7—C6	103.8 (3)	N51—C52—H52	124.4
N7—C7A—N4	112.6 (4)	C52—C53—C53A	106.0 (4)
N7—C7A—S1	138.6 (3)	C52—C53—C51	125.9 (4)
N4—C7A—S1	108.8 (3)	C53A—C53—C51	127.9 (4)
C2—C27—C21	112.2 (11)	C54—C53A—C57A	118.4 (4)
C2—C27—H27A	109.2	C54—C53A—C53	134.5 (4)
C21—C27—H27A	109.2	C57A—C53A—C53	107.1 (4)
C2—C27—H27B	109.2	C55—C54—C53A	118.9 (5)
C21—C27—H27B	109.2	C55—C54—H54	120.6
H27A—C27—H27B	107.9	C53A—C54—H54	120.6
C26—C21—C22	118.9 (6)	C54—C55—C56	121.8 (5)
C26—C21—C27	121.3 (8)	C54—C55—H55	119.1
C22—C21—C27	119.8 (8)	C56—C55—H55	119.1
C21—C22—C23	120.7 (6)	C57—C56—C55	120.5 (6)
C21—C22—H22	119.7	C57—C56—H56	119.7
C23—C22—H22	119.7	C55—C56—H56	119.7
C24—C23—C22	118.7 (6)	C56—C57—C57A	118.5 (5)
C24—C23—H23	120.6	C56—C57—H57	120.7
C22—C23—H23	120.6	C57A—C57—H57	120.7
C25—C24—C23	122.2 (6)	N51—C57A—C57	130.6 (5)
C25—C24—Cl24	119.9 (7)	N51—C57A—C53A	107.5 (4)
C23—C24—Cl24	118.0 (7)	C57—C57A—C53A	121.9 (5)
C24—C25—C26	118.5 (8)	C62—C61—C66	117.8 (4)
C24—C25—H25	120.7	C62—C61—C6	121.5 (4)
C26—C25—H25	120.7	C66—C61—C6	120.7 (4)
C21—C26—C25	120.9 (8)	C61—C62—C63	121.3 (5)
C21—C26—H26	119.5	C61—C62—H62	119.4
C25—C26—H26	119.5	C63—C62—H62	119.4
C36—C31—C32	118.0 (16)	C64—C63—C62	119.2 (5)
C31—C32—C33	120.9 (15)	C64—C63—H63	120.4
C31—C32—H32	119.5	C62—C63—H63	120.4
C33—C32—H32	119.5	C65—C64—C63	121.1 (4)
C34—C33—C32	118.8 (16)	C65—C64—Br64	120.0 (4)
C34—C33—H33	120.6	C63—C64—Br64	118.9 (4)
C32—C33—H33	120.6	C64—C65—C66	118.6 (5)
C35—C34—C33	121.2 (15)	C64—C65—H65	120.7
C35—C34—Cl34	118.7 (16)	C66—C65—H65	120.7
C33—C34—Cl34	119.7 (16)	C61—C66—C65	121.8 (4)
C34—C35—C36	119.5 (16)	C61—C66—H66	119.1
C34—C35—H35	120.3	C65—C66—H66	119.1
C36—C35—H35	120.3
C7A—S1—C2—N3	0.9 (4)	C33—C34—C35—C36	2 (12)
C7A—S1—C2—C27	179.7 (4)	Cl34—C34—C35—C36	175 (5)
C27—C2—N3—N4	−179.2 (4)	C32—C31—C36—C35	3 (17)
S1—C2—N3—N4	−0.4 (5)	C34—C35—C36—C31	−1 (13)
C2—N3—N4—C7A	−0.5 (5)	C6—C5—C51—C53	−116.0 (5)
C2—N3—N4—C5	179.4 (4)	N4—C5—C51—C53	66.0 (5)
C7A—N4—C5—C6	−0.8 (4)	C57A—N51—C52—C53	−0.3 (5)
N3—N4—C5—C6	179.2 (4)	N51—C52—C53—C53A	−0.3 (5)
C7A—N4—C5—C51	177.7 (4)	N51—C52—C53—C51	−175.2 (4)
N3—N4—C5—C51	−2.3 (6)	C5—C51—C53—C52	−133.1 (4)
N4—C5—C6—N7	0.0 (4)	C5—C51—C53—C53A	53.1 (6)
C51—C5—C6—N7	−178.3 (4)	C52—C53—C53A—C54	−179.6 (5)
N4—C5—C6—C61	−176.0 (4)	C51—C53—C53A—C54	−4.8 (8)
C51—C5—C6—C61	5.7 (8)	C52—C53—C53A—C57A	0.8 (5)
C5—C6—N7—C7A	0.8 (5)	C51—C53—C53A—C57A	175.5 (4)
C61—C6—N7—C7A	177.2 (4)	C57A—C53A—C54—C55	1.3 (6)
C6—N7—C7A—N4	−1.4 (5)	C53—C53A—C54—C55	−178.3 (4)
C6—N7—C7A—S1	179.0 (4)	C53A—C54—C55—C56	0.2 (7)
N3—N4—C7A—N7	−178.6 (4)	C54—C55—C56—C57	−1.1 (8)
C5—N4—C7A—N7	1.5 (5)	C55—C56—C57—C57A	0.5 (8)
N3—N4—C7A—S1	1.2 (5)	C52—N51—C57A—C57	−177.9 (5)
C5—N4—C7A—S1	−178.8 (3)	C52—N51—C57A—C53A	0.8 (5)
C2—S1—C7A—N7	178.6 (5)	C56—C57—C57A—N51	179.4 (5)
C2—S1—C7A—N4	−1.1 (3)	C56—C57—C57A—C53A	0.9 (7)
N3—C2—C27—C21	89.1 (8)	C54—C53A—C57A—N51	179.3 (4)
S1—C2—C27—C21	−89.6 (7)	C53—C53A—C57A—N51	−0.9 (5)
C2—C27—C21—C26	−93.1 (19)	C54—C53A—C57A—C57	−1.9 (6)
C2—C27—C21—C22	87 (2)	C53—C53A—C57A—C57	177.8 (4)
C26—C21—C22—C23	−1 (3)	C5—C6—C61—C62	−41.3 (6)
C27—C21—C22—C23	179.7 (13)	N7—C6—C61—C62	142.9 (4)
C21—C22—C23—C24	−1.3 (16)	C5—C6—C61—C66	136.5 (5)
C22—C23—C24—C25	1.6 (11)	N7—C6—C61—C66	−39.2 (6)
C22—C23—C24—Cl24	−176.5 (5)	C66—C61—C62—C63	−4.0 (7)
C23—C24—C25—C26	0.0 (13)	C6—C61—C62—C63	173.9 (4)
Cl24—C24—C25—C26	178.0 (7)	C61—C62—C63—C64	1.6 (7)
C22—C21—C26—C25	2 (3)	C62—C63—C64—C65	2.1 (8)
C27—C21—C26—C25	−178.1 (14)	C62—C63—C64—Br64	−175.6 (4)
C24—C25—C26—C21	−1.9 (19)	C63—C64—C65—C66	−3.0 (8)
C36—C31—C32—C33	−7 (16)	Br64—C64—C65—C66	174.6 (4)
C31—C32—C33—C34	9 (10)	C62—C61—C66—C65	3.0 (7)
C32—C33—C34—C35	−6 (9)	C6—C61—C66—C65	−174.9 (4)
C32—C33—C34—Cl34	−178 (4)	C64—C65—C66—C61	0.5 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51···N7^i	0.99 (5)	1.97 (5)	2.941 (5)	166 (4)
C51—H51A···Cg1^ii	0.97	2.97	3.699 (5)	133
C62—H62···Cg2^ii	0.93	2.91	3.757 (5)	152
C65—H65···Cg3^iii	0.93	2.82	3.412 (7)	123
C65—H65···Cg4^iii	0.93	2.91	3.60 (3)	131

Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+3/2, −y+1, z−1/2.