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Six closely related N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]aryl­amides have been synthesized and structurally characterized, together with a repre­sentative reaction inter­mediate. In each of N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]benzamide, C20H16ClNO2S, (I), N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-4-phenyl­benzamide, C26H20ClNO2S, (II), and 2-bromo-N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]benzamide, C20H15BrClNO2S, (III), the mol­ecules are disordered over two sets of atomic sites, with occupancies of 0.894 (8) and 0.106 (8) in (I), 0.832 (5) and 0.168 (5) in (II), and 0.7006 (12) and 0.2994 (12) in (III). In each of N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2-iodo­benzamide, C20H15ClINO2S, (IV), and N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2-meth­oxy­benzamide, C21H18ClNO3S, (V), the mol­ecules are fully ordered, but in N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2,6-di­fluoro­benzamide, C20H14ClF2NO2S, (VI), which crystallizes with Z′ = 2 in the space group C2/c, one of the two independent mol­ecules is fully ordered, while the other is disordered over two sets of atomic sites having occupancies of 0.916 (3) and 0.084 (3). All of the mol­ecules in compounds (I)–(VI) exhibit an intra­molecular N—H...O hydrogen bond. The mol­ecules of (I) and (VI) are linked by C—H...O hydrogen bonds to form finite zero-dimensional dimers, which are cyclic in (I) and acyclic in (VI), those of (III) are linked by C—H...π(arene) hydrogen bonds to form simple chains, and those of (IV) and (V) are linked into different types of chains of rings, built in each case from a combination of C—H...O and C—H...π(arene) hydrogen bonds. Two C—H...O hydrogen bonds link the mol­ecules of (II) into sheets containing three types of ring. In benzotriazol-1-yl 3,4-di­meth­oxy­benzoate, C15H13N3O4, (VII), the benzoate component is planar and makes a dihedral angle of 84.51 (6)° with the benzotriazole unit. Comparisons are made with related compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618000657/sk3680sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680VIsup7.hkl
Contains datablock VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680VIIsup8.hkl
Contains datablock VII

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680Isup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IIsup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IIIsup11.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IVsup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680Vsup13.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680VIsup14.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680VIIsup15.cml
Supplementary material

CCDC references: 1816131; 1816130; 1816129; 1816128; 1816127; 1816126; 1816125

Computing details top

For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide (I) top
Crystal data top
C20H16ClNO2SF(000) = 768
Mr = 369.85Dx = 1.374 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.7868 (9) ÅCell parameters from 4162 reflections
b = 13.9567 (12) Åθ = 2.1–27.6°
c = 13.3764 (11) ŵ = 0.34 mm1
β = 101.816 (2)°T = 294 K
V = 1788.4 (3) Å3Block, yellow
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2092 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.058
φ and ω scansθmax = 26.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1212
Tmin = 0.864, Tmax = 0.934k = 1717
26489 measured reflectionsl = 1616
3726 independent reflections
Refinement top
Refinement on F272 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.5759P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3726 reflectionsΔρmax = 0.20 e Å3
304 parametersΔρmin = 0.26 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.4662 (5)0.4257 (5)0.6023 (6)0.0450 (7)0.894 (8)
O110.5871 (4)0.4022 (3)0.6349 (4)0.0654 (14)0.894 (8)
N110.3840 (6)0.3740 (4)0.5264 (5)0.0469 (9)0.894 (8)
H110.29940.39320.50550.056*0.894 (8)
C1110.3996 (4)0.5092 (4)0.6421 (5)0.0394 (9)0.894 (8)
C1120.4867 (4)0.5772 (4)0.6982 (5)0.0482 (11)0.894 (8)
H1120.58300.57080.70710.058*0.894 (8)
C1130.4309 (5)0.6544 (4)0.7409 (6)0.0567 (11)0.894 (8)
H1130.48980.69930.77910.068*0.894 (8)
C1140.2884 (5)0.6649 (4)0.7270 (6)0.0618 (12)0.894 (8)
H1140.25120.71770.75450.074*0.894 (8)
C1150.2014 (5)0.5981 (5)0.6728 (6)0.0608 (11)0.894 (8)
H1150.10520.60450.66500.073*0.894 (8)
C1160.2564 (4)0.5205 (5)0.6295 (8)0.0509 (10)0.894 (8)
H1160.19680.47580.59170.061*0.894 (8)
S1210.5895 (2)0.24663 (19)0.51192 (17)0.0545 (4)0.894 (8)
C1220.4252 (4)0.2938 (4)0.4807 (5)0.0424 (7)0.894 (8)
C1230.3390 (5)0.2415 (5)0.4055 (5)0.0430 (8)0.894 (8)
C1240.4093 (5)0.1595 (4)0.3766 (4)0.0520 (14)0.894 (8)
H1240.36690.11580.32740.062*0.894 (8)
C1250.5426 (5)0.1516 (4)0.4272 (3)0.0610 (11)0.894 (8)
C1260.6508 (6)0.0790 (4)0.4134 (4)0.1070 (15)0.894 (8)
H16A0.60420.01780.39850.128*0.894 (8)
H16B0.68630.09730.35350.128*0.894 (8)
C1270.7653 (6)0.0650 (4)0.4936 (4)0.118 (2)0.894 (8)
H17A0.81780.12340.50630.178*0.894 (8)
H17B0.82360.01530.47560.178*0.894 (8)
H17C0.73300.04670.55400.178*0.894 (8)
C1370.1991 (4)0.2729 (3)0.3611 (3)0.0493 (8)0.894 (8)
O1370.1483 (6)0.3470 (6)0.3882 (10)0.0763 (10)0.894 (8)
C1310.1082 (4)0.2122 (3)0.2808 (3)0.0471 (8)0.894 (8)
C1320.0831 (4)0.2350 (2)0.1786 (3)0.0529 (8)0.894 (8)
Cl120.1722 (4)0.32924 (12)0.13678 (12)0.0900 (6)0.894 (8)
C1330.0123 (7)0.1840 (4)0.1081 (3)0.0660 (10)0.894 (8)
H1330.02910.20100.03940.079*0.894 (8)
C1340.0821 (5)0.1085 (3)0.1395 (4)0.0696 (13)0.894 (8)
H1340.14700.07460.09210.084*0.894 (8)
C1350.0571 (5)0.0828 (3)0.2396 (4)0.0736 (13)0.894 (8)
H1350.10350.03080.26070.088*0.894 (8)
C1360.0383 (7)0.1348 (4)0.3097 (4)0.0667 (10)0.894 (8)
H1360.05550.11690.37810.080*0.894 (8)
C210.458 (4)0.432 (4)0.600 (5)0.0450 (7)0.106 (8)
O210.584 (3)0.423 (3)0.619 (4)0.0654 (14)0.106 (8)
N210.379 (5)0.384 (4)0.519 (4)0.0469 (9)0.106 (8)
H210.30340.41070.48830.056*0.106 (8)
C2110.382 (3)0.504 (3)0.650 (4)0.0394 (9)0.106 (8)
C2120.461 (3)0.576 (3)0.707 (5)0.0482 (11)0.106 (8)
H2120.55720.56800.72830.058*0.106 (8)
C2130.397 (4)0.658 (3)0.731 (6)0.0567 (11)0.106 (8)
H2130.45050.71070.75850.068*0.106 (8)
C2140.253 (5)0.663 (4)0.715 (6)0.0618 (12)0.106 (8)
H2140.21040.71270.74270.074*0.106 (8)
C2150.175 (4)0.594 (4)0.657 (6)0.0608 (11)0.106 (8)
H2150.07880.60270.63540.073*0.106 (8)
C2160.238 (3)0.512 (5)0.630 (7)0.0509 (10)0.106 (8)
H2160.18330.46110.59950.061*0.106 (8)
S2210.566 (2)0.2386 (18)0.5242 (16)0.0545 (4)0.106 (8)
C2220.411 (3)0.296 (3)0.483 (4)0.0424 (7)0.106 (8)
C2230.329 (3)0.250 (4)0.401 (4)0.0430 (8)0.106 (8)
C2240.404 (4)0.174 (4)0.365 (4)0.0520 (14)0.106 (8)
H2240.36390.13310.31150.062*0.106 (8)
C2250.538 (4)0.167 (3)0.415 (2)0.0610 (11)0.106 (8)
C2260.641 (4)0.089 (3)0.407 (3)0.1070 (15)0.106 (8)
H26A0.60820.05490.34310.128*0.106 (8)
H26B0.72900.11890.40230.128*0.106 (8)
C2270.668 (6)0.021 (3)0.485 (3)0.118 (2)0.106 (8)
H27A0.59920.02910.47160.178*0.106 (8)
H27B0.66350.05130.54900.178*0.106 (8)
H27C0.75910.00580.48910.178*0.106 (8)
C2370.182 (3)0.271 (2)0.3688 (17)0.0493 (8)0.106 (8)
O2370.131 (5)0.348 (5)0.388 (9)0.0763 (10)0.106 (8)
C2310.092 (4)0.207 (2)0.2915 (17)0.0471 (8)0.106 (8)
C2320.060 (2)0.2286 (12)0.1890 (14)0.0529 (8)0.106 (8)
Cl220.116 (2)0.3359 (12)0.1463 (12)0.0900 (6)0.106 (8)
C2330.015 (6)0.166 (2)0.119 (2)0.0660 (10)0.106 (8)
H2330.03260.18010.04970.079*0.106 (8)
C2340.064 (5)0.082 (2)0.152 (3)0.0696 (13)0.106 (8)
H2340.11830.04110.10530.084*0.106 (8)
C2350.033 (5)0.058 (2)0.253 (3)0.0736 (13)0.106 (8)
H2350.06460.00070.27480.088*0.106 (8)
C2360.045 (6)0.121 (3)0.322 (2)0.0667 (10)0.106 (8)
H2360.06670.10440.39070.080*0.106 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0384 (17)0.0543 (19)0.0391 (14)0.0016 (13)0.0007 (12)0.0015 (14)
O110.0427 (12)0.079 (3)0.066 (2)0.0094 (14)0.0089 (12)0.021 (2)
N110.0384 (13)0.0531 (19)0.0437 (16)0.0060 (12)0.0049 (10)0.0070 (16)
C1110.0350 (17)0.0488 (16)0.0328 (17)0.0006 (14)0.0030 (14)0.0030 (14)
C1120.043 (2)0.0629 (19)0.039 (2)0.0073 (17)0.0076 (18)0.0010 (14)
C1130.060 (3)0.0585 (19)0.049 (3)0.009 (2)0.006 (3)0.0108 (17)
C1140.067 (4)0.065 (2)0.053 (3)0.012 (2)0.010 (3)0.0077 (16)
C1150.047 (2)0.074 (2)0.058 (3)0.013 (2)0.002 (2)0.005 (2)
C1160.042 (2)0.057 (2)0.0502 (16)0.0018 (17)0.001 (2)0.0079 (19)
S1210.0413 (8)0.0731 (7)0.0446 (7)0.0114 (7)0.0020 (5)0.0082 (5)
C1220.0379 (17)0.0509 (15)0.0364 (13)0.0016 (13)0.0029 (13)0.0005 (12)
C1230.0367 (15)0.049 (2)0.0400 (15)0.0028 (12)0.0009 (11)0.0026 (15)
C1240.0530 (18)0.054 (3)0.045 (2)0.0065 (15)0.0005 (14)0.010 (2)
C1250.0558 (19)0.069 (3)0.052 (2)0.0186 (17)0.0041 (15)0.0120 (18)
C1260.089 (3)0.122 (4)0.094 (3)0.057 (3)0.019 (2)0.041 (3)
C1270.093 (4)0.122 (4)0.123 (4)0.061 (4)0.019 (3)0.032 (3)
C1370.0412 (18)0.0552 (17)0.0483 (16)0.0001 (14)0.0019 (13)0.0091 (13)
O1370.049 (2)0.0768 (15)0.0895 (15)0.0200 (16)0.017 (2)0.0348 (12)
C1310.0347 (18)0.0518 (17)0.0522 (17)0.0019 (13)0.0022 (13)0.0077 (13)
C1320.0444 (18)0.0575 (18)0.0534 (17)0.0037 (14)0.0020 (14)0.0080 (14)
Cl120.1077 (16)0.0914 (7)0.0720 (6)0.0329 (9)0.0209 (8)0.0019 (5)
C1330.060 (2)0.074 (3)0.0564 (19)0.002 (2)0.0056 (17)0.0107 (18)
C1340.046 (2)0.072 (3)0.082 (3)0.003 (2)0.0066 (19)0.026 (2)
C1350.061 (3)0.063 (3)0.097 (3)0.016 (2)0.016 (2)0.012 (2)
C1360.070 (2)0.064 (3)0.063 (2)0.009 (2)0.0065 (18)0.0004 (17)
C210.0384 (17)0.0543 (19)0.0391 (14)0.0016 (13)0.0007 (12)0.0015 (14)
O210.0427 (12)0.079 (3)0.066 (2)0.0094 (14)0.0089 (12)0.021 (2)
N210.0384 (13)0.0531 (19)0.0437 (16)0.0060 (12)0.0049 (10)0.0070 (16)
C2110.0350 (17)0.0488 (16)0.0328 (17)0.0006 (14)0.0030 (14)0.0030 (14)
C2120.043 (2)0.0629 (19)0.039 (2)0.0073 (17)0.0076 (18)0.0010 (14)
C2130.060 (3)0.0585 (19)0.049 (3)0.009 (2)0.006 (3)0.0108 (17)
C2140.067 (4)0.065 (2)0.053 (3)0.012 (2)0.010 (3)0.0077 (16)
C2150.047 (2)0.074 (2)0.058 (3)0.013 (2)0.002 (2)0.005 (2)
C2160.042 (2)0.057 (2)0.0502 (16)0.0018 (17)0.001 (2)0.0079 (19)
S2210.0413 (8)0.0731 (7)0.0446 (7)0.0114 (7)0.0020 (5)0.0082 (5)
C2220.0379 (17)0.0509 (15)0.0364 (13)0.0016 (13)0.0029 (13)0.0005 (12)
C2230.0367 (15)0.049 (2)0.0400 (15)0.0028 (12)0.0009 (11)0.0026 (15)
C2240.0530 (18)0.054 (3)0.045 (2)0.0065 (15)0.0005 (14)0.010 (2)
C2250.0558 (19)0.069 (3)0.052 (2)0.0186 (17)0.0041 (15)0.0120 (18)
C2260.089 (3)0.122 (4)0.094 (3)0.057 (3)0.019 (2)0.041 (3)
C2270.093 (4)0.122 (4)0.123 (4)0.061 (4)0.019 (3)0.032 (3)
C2370.0412 (18)0.0552 (17)0.0483 (16)0.0001 (14)0.0019 (13)0.0091 (13)
O2370.049 (2)0.0768 (15)0.0895 (15)0.0200 (16)0.017 (2)0.0348 (12)
C2310.0347 (18)0.0518 (17)0.0522 (17)0.0019 (13)0.0022 (13)0.0077 (13)
C2320.0444 (18)0.0575 (18)0.0534 (17)0.0037 (14)0.0020 (14)0.0080 (14)
Cl220.1077 (16)0.0914 (7)0.0720 (6)0.0329 (9)0.0209 (8)0.0019 (5)
C2330.060 (2)0.074 (3)0.0564 (19)0.002 (2)0.0056 (17)0.0107 (18)
C2340.046 (2)0.072 (3)0.082 (3)0.003 (2)0.0066 (19)0.026 (2)
C2350.061 (3)0.063 (3)0.097 (3)0.016 (2)0.016 (2)0.012 (2)
C2360.070 (2)0.064 (3)0.063 (2)0.009 (2)0.0065 (18)0.0004 (17)
Geometric parameters (Å, º) top
C11—O111.219 (3)C21—O211.219 (6)
C11—N111.365 (3)C21—N211.365 (6)
C11—C1111.487 (4)C21—C2111.488 (6)
N11—C1221.376 (3)N21—C2221.375 (6)
N11—H110.8600N21—H210.8600
C111—C1161.385 (3)C211—C2161.386 (5)
C111—C1121.389 (3)C211—C2121.389 (6)
C112—C1131.384 (4)C212—C2131.385 (6)
C112—H1120.9300C212—H2120.9300
C113—C1141.377 (4)C213—C2141.377 (6)
C113—H1130.9300C213—H2130.9300
C114—C1151.367 (4)C214—C2151.368 (6)
C114—H1140.9300C214—H2140.9300
C115—C1161.387 (4)C215—C2161.388 (6)
C115—H1150.9300C215—H2150.9300
C116—H1160.9300C216—H2160.9300
S121—C1221.708 (3)S221—C2221.708 (5)
S121—C1251.744 (3)S221—C2251.747 (6)
C122—C1231.381 (3)C222—C2231.383 (5)
C123—C1241.429 (3)C223—C2241.429 (5)
C123—C1371.444 (4)C223—C2371.445 (6)
C124—C1251.346 (4)C224—C2251.349 (6)
C124—H1240.9300C224—H2240.9300
C125—C1261.503 (4)C225—C2261.507 (6)
C126—C1271.397 (6)C226—C2271.398 (8)
C126—H16A0.9700C226—H26A0.9700
C126—H16B0.9700C226—H26B0.9700
C127—H17A0.9600C227—H27A0.9600
C127—H17B0.9600C227—H27B0.9600
C127—H17C0.9600C227—H27C0.9600
C137—O1371.235 (3)C237—O2371.236 (6)
C137—C1311.507 (4)C237—C2311.507 (5)
C131—C1361.376 (4)C231—C2361.375 (6)
C131—C1321.377 (4)C231—C2321.376 (5)
C132—C1331.380 (4)C232—C2331.380 (6)
C132—Cl121.733 (3)C232—Cl221.733 (5)
C133—C1341.368 (5)C233—C2341.368 (6)
C133—H1330.9300C233—H2330.9300
C134—C1351.359 (5)C234—C2351.358 (7)
C134—H1340.9300C234—H2340.9300
C135—C1361.386 (4)C235—C2361.386 (6)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O11—C11—N11120.4 (3)O21—C21—N21120.2 (10)
O11—C11—C111123.2 (2)O21—C21—C211123.1 (9)
N11—C11—C111116.4 (2)N21—C21—C211116.0 (8)
C11—N11—C122125.4 (3)C21—N21—C222125.8 (11)
C11—N11—H11117.3C21—N21—H21117.1
C122—N11—H11117.3C222—N21—H21117.1
C116—C111—C112118.8 (2)C216—C211—C212118.7 (6)
C116—C111—C11123.5 (2)C216—C211—C21123.1 (8)
C112—C111—C11117.6 (2)C212—C211—C21117.5 (8)
C113—C112—C111120.3 (3)C213—C212—C211119.9 (8)
C113—C112—H112119.8C213—C212—H212120.0
C111—C112—H112119.8C211—C212—H212120.0
C114—C113—C112120.1 (3)C214—C213—C212119.9 (9)
C114—C113—H113119.9C214—C213—H213120.1
C112—C113—H113119.9C212—C213—H213120.1
C115—C114—C113120.2 (3)C215—C214—C213119.8 (9)
C115—C114—H114119.9C215—C214—H214120.1
C113—C114—H114119.9C213—C214—H214120.1
C114—C115—C116120.1 (3)C214—C215—C216119.7 (9)
C114—C115—H115119.9C214—C215—H215120.1
C116—C115—H115119.9C216—C215—H215120.1
C111—C116—C115120.5 (3)C211—C216—C215120.4 (8)
C111—C116—H116119.8C211—C216—H216119.8
C115—C116—H116119.8C215—C216—H216119.8
C122—S121—C12591.45 (15)C222—S221—C22591.1 (4)
N11—C122—C123124.2 (2)N21—C222—C223124.0 (9)
N11—C122—S121123.5 (2)N21—C222—S221123.7 (8)
C123—C122—S121112.2 (2)C223—C222—S221111.8 (5)
C122—C123—C124111.4 (2)C222—C223—C224111.2 (5)
C122—C123—C137121.7 (2)C222—C223—C237121.4 (9)
C124—C123—C137126.8 (2)C224—C223—C237126.9 (9)
C125—C124—C123113.6 (3)C225—C224—C223113.4 (6)
C125—C124—H124123.2C225—C224—H224123.3
C123—C124—H124123.2C223—C224—H224123.3
C124—C125—C126128.9 (3)C224—C225—C226128.0 (9)
C124—C125—S121111.3 (2)C224—C225—S221110.5 (7)
C126—C125—S121119.6 (3)C226—C225—S221118.6 (7)
C127—C126—C125118.3 (3)C227—C226—C225117.5 (9)
C127—C126—H16A107.7C227—C226—H26A107.9
C125—C126—H16A107.7C225—C226—H26A107.9
C127—C126—H16B107.7C227—C226—H26B107.9
C125—C126—H16B107.7C225—C226—H26B107.9
H16A—C126—H16B107.1H26A—C226—H26B107.2
C126—C127—H17A109.5C226—C227—H27A109.5
C126—C127—H17B109.5C226—C227—H27B109.5
H17A—C127—H17B109.5H27A—C227—H27B109.5
C126—C127—H17C109.5C226—C227—H27C109.5
H17A—C127—H17C109.5H27A—C227—H27C109.5
H17B—C127—H17C109.5H27B—C227—H27C109.5
O137—C137—C123122.6 (3)O237—C237—C223122.2 (10)
O137—C137—C131117.7 (3)O237—C237—C231117.4 (8)
C123—C137—C131119.7 (2)C223—C237—C231119.2 (8)
C136—C131—C132117.5 (3)C236—C231—C232117.7 (6)
C136—C131—C137119.8 (3)C236—C231—C237119.8 (7)
C132—C131—C137122.5 (3)C232—C231—C237122.4 (7)
C131—C132—C133121.2 (3)C231—C232—C233121.1 (6)
C131—C132—Cl12119.8 (2)C231—C232—Cl22119.7 (6)
C133—C132—Cl12119.0 (2)C233—C232—Cl22119.2 (6)
C134—C133—C132119.8 (3)C234—C233—C232119.8 (7)
C134—C133—H133120.1C234—C233—H233120.1
C132—C133—H133120.1C232—C233—H233120.1
C135—C134—C133120.4 (3)C235—C234—C233120.5 (7)
C135—C134—H134119.8C235—C234—H234119.8
C133—C134—H134119.8C233—C234—H234119.8
C134—C135—C136119.3 (3)C234—C235—C236119.2 (7)
C134—C135—H135120.4C234—C235—H235120.4
C136—C135—H135120.4C236—C235—H235120.4
C131—C136—C135121.7 (3)C231—C236—C235121.7 (7)
C131—C136—H136119.1C231—C236—H236119.2
C135—C136—H136119.1C235—C236—H236119.2
O11—C11—N11—C1220.2 (11)O21—C21—N21—C22232 (9)
C111—C11—N11—C122179.0 (8)C211—C21—N21—C222158 (7)
O11—C11—C111—C116159.8 (8)O21—C21—C211—C216178 (8)
N11—C11—C111—C11619.4 (9)N21—C21—C211—C21612 (8)
O11—C11—C111—C11217.6 (10)O21—C21—C211—C21212 (8)
N11—C11—C111—C112163.2 (6)N21—C21—C211—C212158 (5)
C116—C111—C112—C1130.3 (8)C216—C211—C212—C2138 (8)
C11—C111—C112—C113177.2 (7)C21—C211—C212—C213162 (7)
C111—C112—C113—C1140.8 (10)C211—C212—C213—C21411 (9)
C112—C113—C114—C1151.4 (10)C212—C213—C214—C21513 (10)
C113—C114—C115—C1161.6 (11)C213—C214—C215—C21611 (10)
C112—C111—C116—C1150.4 (10)C212—C211—C216—C2157 (9)
C11—C111—C116—C115176.9 (9)C21—C211—C216—C215163 (8)
C114—C115—C116—C1111.1 (12)C214—C215—C216—C2119 (11)
C11—N11—C122—C123178.5 (7)C21—N21—C222—C223180 (5)
C11—N11—C122—S1210.7 (11)C21—N21—C222—S2219 (9)
C125—S121—C122—N11176.9 (7)C225—S221—C222—N21160 (6)
C125—S121—C122—C1232.4 (5)C225—S221—C222—C22311 (4)
N11—C122—C123—C124177.1 (8)N21—C222—C223—C224165 (7)
S121—C122—C123—C1242.1 (7)S221—C222—C223—C2247 (6)
N11—C122—C123—C1376.1 (10)N21—C222—C223—C23723 (8)
S121—C122—C123—C137174.6 (7)S221—C222—C223—C237165 (6)
C122—C123—C124—C1250.6 (8)C222—C223—C224—C2253 (7)
C137—C123—C124—C125175.9 (7)C237—C223—C224—C225175 (6)
C123—C124—C125—C126176.1 (6)C223—C224—C225—C226171 (5)
C123—C124—C125—S1211.1 (7)C223—C224—C225—S22112 (6)
C122—S121—C125—C1242.0 (5)C222—S221—C225—C22413 (4)
C122—S121—C125—C126177.5 (5)C222—S221—C225—C226175 (3)
C124—C125—C126—C127159.7 (8)C224—C225—C226—C227103 (6)
S121—C125—C126—C12725.8 (8)S221—C225—C226—C22756 (4)
C122—C123—C137—O1370.9 (11)C222—C223—C237—O23724 (9)
C124—C123—C137—O137177.1 (12)C224—C223—C237—O237165 (10)
C122—C123—C137—C131178.7 (5)C222—C223—C237—C231169 (3)
C124—C123—C137—C1315.1 (10)C224—C223—C237—C2312 (8)
O137—C137—C131—C13696.8 (10)O237—C237—C231—C236113 (8)
C123—C137—C131—C13681.2 (6)C223—C237—C231—C23680 (5)
O137—C137—C131—C13278.3 (10)O237—C237—C231—C23271 (8)
C123—C137—C131—C132103.8 (5)C223—C237—C231—C23297 (4)
C136—C131—C132—C1332.2 (5)C236—C231—C232—C2331 (3)
C137—C131—C132—C133173.0 (5)C237—C231—C232—C233176 (4)
C136—C131—C132—Cl12177.9 (3)C236—C231—C232—Cl22180 (2)
C137—C131—C132—Cl127.0 (5)C237—C231—C232—Cl223 (3)
C131—C132—C133—C1341.0 (7)C231—C232—C233—C2343 (5)
Cl12—C132—C133—C134179.0 (4)Cl22—C232—C233—C234178 (3)
C132—C133—C134—C1350.6 (8)C232—C233—C234—C2353 (6)
C133—C134—C135—C1361.0 (7)C233—C234—C235—C2361 (6)
C132—C131—C136—C1351.8 (7)C232—C231—C236—C2351 (5)
C137—C131—C136—C135173.5 (5)C237—C231—C236—C235178 (4)
C134—C135—C136—C1310.2 (8)C234—C235—C236—C2311 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1370.862.032.671 (12)131
N21—H21···O2370.862.122.73 (10)129
C115—H115···O137i0.932.533.438 (9)166
C215—H215···O237i0.932.133.04 (7)166
Symmetry code: (i) x, y+1, z+1.
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-4-phenylbenzamide (II) top
Crystal data top
C26H20ClNO2SF(000) = 928
Mr = 445.94Dx = 1.325 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.7264 (6) ÅCell parameters from 7049 reflections
b = 9.1208 (5) Åθ = 1.8–30.9°
c = 22.9103 (15) ŵ = 0.29 mm1
β = 94.414 (2)°T = 296 K
V = 2234.7 (2) Å3Block, colourless
Z = 40.28 × 0.27 × 0.22 mm
Data collection top
Bruker Kappa APEXII
diffractometer
3570 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.033
φ and ω scansθmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1313
Tmin = 0.929, Tmax = 0.939k = 1111
24401 measured reflectionsl = 2928
5148 independent reflections
Refinement top
Refinement on F289 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0487P)2 + 1.1314P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5148 reflectionsΔρmax = 0.39 e Å3
373 parametersΔρmin = 0.35 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.3958 (6)0.7159 (4)0.49542 (14)0.0388 (11)0.832 (5)
O110.40738 (18)0.81059 (17)0.45845 (7)0.0652 (5)0.832 (5)
N110.3397 (12)0.5857 (6)0.4797 (3)0.0398 (10)0.832 (5)
H110.33730.51950.50640.048*0.832 (5)
C1110.4457 (9)0.7310 (4)0.55744 (15)0.0352 (11)0.832 (5)
C1120.5052 (6)0.8626 (4)0.57421 (17)0.0441 (13)0.832 (5)
H1120.51030.93750.54700.053*0.832 (5)
C1130.5562 (5)0.8822 (5)0.63050 (16)0.0449 (12)0.832 (5)
H1130.59460.97090.64070.054*0.832 (5)
C1140.5519 (14)0.7726 (8)0.6727 (3)0.0391 (5)0.832 (5)
C1150.4928 (14)0.6418 (7)0.6557 (2)0.0430 (15)0.832 (5)
H1150.48750.56710.68310.052*0.832 (5)
C1160.4418 (11)0.6208 (5)0.59912 (17)0.0410 (15)0.832 (5)
H1160.40440.53160.58880.049*0.832 (5)
S1210.2951 (2)0.66308 (19)0.36452 (9)0.0482 (4)0.832 (5)
C1220.2865 (7)0.5520 (5)0.42463 (16)0.0361 (11)0.832 (5)
C1230.2174 (7)0.4269 (5)0.41147 (18)0.0374 (11)0.832 (5)
C1240.1733 (3)0.4230 (3)0.35089 (14)0.0421 (10)0.832 (5)
H1240.12540.34640.33440.050*0.832 (5)
C1250.2070 (4)0.5394 (4)0.32011 (13)0.0498 (11)0.832 (5)
C1260.1811 (4)0.5720 (4)0.25571 (13)0.0697 (12)0.832 (5)
H16A0.25920.56910.23710.084*0.832 (5)
H16B0.12720.49600.23810.084*0.832 (5)
C1270.1202 (6)0.7183 (5)0.24404 (19)0.123 (2)0.832 (5)
H17A0.09150.72520.20340.185*0.832 (5)
H17B0.17970.79480.25370.185*0.832 (5)
H17C0.05050.72850.26760.185*0.832 (5)
C1370.1907 (3)0.3189 (4)0.45606 (18)0.0384 (6)0.832 (5)
O1370.2433 (7)0.3199 (7)0.5056 (2)0.0531 (14)0.832 (5)
C1310.0991 (3)0.1982 (3)0.4394 (3)0.0427 (5)0.832 (5)
C1320.0272 (3)0.2248 (3)0.42736 (15)0.0510 (8)0.832 (5)
Cl120.08524 (14)0.4023 (2)0.43201 (9)0.0749 (4)0.832 (5)
C1330.1105 (4)0.1119 (5)0.4147 (3)0.0758 (14)0.832 (5)
H1330.19540.13140.40740.091*0.832 (5)
C1340.0674 (5)0.0279 (5)0.4131 (5)0.0955 (19)0.832 (5)
H1340.12320.10420.40420.115*0.832 (5)
C1350.0577 (5)0.0580 (4)0.4244 (5)0.0921 (13)0.832 (5)
H1350.08610.15410.42260.111*0.832 (5)
C1360.1416 (4)0.0547 (4)0.4384 (4)0.0625 (10)0.832 (5)
H1360.22600.03420.44700.075*0.832 (5)
C1410.6107 (9)0.7926 (10)0.73308 (18)0.0418 (11)0.832 (5)
C1420.7192 (14)0.8753 (18)0.7432 (3)0.0574 (11)0.832 (5)
H1420.75360.92120.71200.069*0.832 (5)
C1430.7770 (11)0.8902 (12)0.7991 (3)0.0649 (12)0.832 (5)
H1430.85010.94480.80500.078*0.832 (5)
C1440.7267 (4)0.8248 (7)0.84572 (17)0.0556 (11)0.832 (5)
H1440.76430.83760.88330.067*0.832 (5)
C1450.6218 (5)0.7410 (8)0.83703 (17)0.0573 (12)0.832 (5)
H1450.58880.69460.86860.069*0.832 (5)
C1460.5641 (6)0.7248 (9)0.7809 (2)0.0515 (15)0.832 (5)
H1460.49260.66730.77540.062*0.832 (5)
C210.412 (4)0.7075 (17)0.4927 (7)0.0388 (11)0.168 (5)
O210.40738 (18)0.81059 (17)0.45845 (7)0.0652 (5)0.168 (5)
N210.347 (6)0.582 (3)0.4777 (13)0.0398 (10)0.168 (5)
H210.35360.50960.50180.048*0.168 (5)
C2110.458 (5)0.722 (2)0.5554 (7)0.0352 (11)0.168 (5)
C2120.482 (4)0.864 (2)0.5769 (8)0.0441 (13)0.168 (5)
H2120.46490.94470.55280.053*0.168 (5)
C2130.530 (3)0.884 (3)0.6336 (8)0.0449 (12)0.168 (5)
H2130.55150.97790.64660.054*0.168 (5)
C2140.549 (7)0.766 (4)0.6721 (13)0.0391 (5)0.168 (5)
C2150.502 (8)0.630 (4)0.6532 (11)0.0430 (15)0.168 (5)
H2150.50360.55230.67950.052*0.168 (5)
C2160.455 (6)0.609 (3)0.5960 (9)0.0410 (15)0.168 (5)
H2160.42030.51900.58470.049*0.168 (5)
S2210.2749 (12)0.6821 (11)0.3678 (5)0.0482 (4)0.168 (5)
C2220.273 (4)0.565 (3)0.4264 (8)0.0361 (11)0.168 (5)
C2230.204 (4)0.440 (3)0.4128 (9)0.0374 (11)0.168 (5)
C2240.149 (2)0.4448 (19)0.3538 (7)0.0421 (10)0.168 (5)
H2240.09430.37370.33810.050*0.168 (5)
C2250.184 (2)0.561 (2)0.3232 (5)0.0498 (11)0.168 (5)
C2260.1403 (17)0.606 (2)0.2615 (6)0.0697 (12)0.168 (5)
H26A0.10460.52110.24080.084*0.168 (5)
H26B0.07470.67870.26320.084*0.168 (5)
C2270.243 (2)0.668 (3)0.2278 (8)0.123 (2)0.168 (5)
H27A0.20900.69480.18930.185*0.168 (5)
H27B0.30660.59500.22480.185*0.168 (5)
H27C0.27760.75240.24770.185*0.168 (5)
C2370.2050 (16)0.3146 (18)0.4529 (9)0.0384 (6)0.168 (5)
O2370.263 (4)0.317 (4)0.5013 (12)0.0531 (14)0.168 (5)
C2310.1151 (12)0.1902 (12)0.4391 (13)0.0427 (5)0.168 (5)
C2320.0129 (12)0.2080 (11)0.4390 (7)0.0510 (8)0.168 (5)
Cl220.0753 (9)0.3806 (11)0.4505 (4)0.0749 (4)0.168 (5)
C2330.0937 (17)0.0918 (16)0.4281 (17)0.0758 (14)0.168 (5)
H2330.17970.10690.42540.091*0.168 (5)
C2340.046 (2)0.0447 (17)0.421 (3)0.0955 (19)0.168 (5)
H2340.10060.12370.41480.115*0.168 (5)
C2350.080 (2)0.0673 (16)0.424 (3)0.0921 (13)0.168 (5)
H2350.11180.16170.42020.111*0.168 (5)
C2360.1621 (18)0.0502 (16)0.432 (2)0.0625 (10)0.168 (5)
H2360.24800.03520.43270.075*0.168 (5)
C2410.619 (5)0.783 (5)0.7301 (9)0.0418 (11)0.168 (5)
C2420.715 (7)0.886 (9)0.7380 (15)0.0574 (11)0.168 (5)
H2420.73750.94110.70630.069*0.168 (5)
C2430.778 (6)0.907 (7)0.7926 (16)0.0649 (12)0.168 (5)
H2430.83550.98280.79840.078*0.168 (5)
C2440.753 (3)0.816 (4)0.8380 (10)0.0556 (11)0.168 (5)
H2440.80770.81370.87160.067*0.168 (5)
C2450.649 (3)0.730 (4)0.8336 (8)0.0573 (12)0.168 (5)
H2450.62250.68400.86670.069*0.168 (5)
C2460.584 (4)0.711 (5)0.7794 (11)0.0515 (15)0.168 (5)
H2460.51440.64970.77620.062*0.168 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.043 (2)0.0336 (11)0.0401 (12)0.0061 (12)0.0016 (12)0.0029 (9)
O110.0996 (13)0.0470 (9)0.0461 (9)0.0262 (9)0.0137 (9)0.0143 (7)
N110.049 (2)0.0364 (9)0.0334 (10)0.0076 (11)0.0008 (12)0.0053 (8)
C1110.036 (2)0.0323 (11)0.0374 (11)0.0027 (13)0.0027 (11)0.0008 (9)
C1120.056 (3)0.0357 (11)0.0405 (12)0.0113 (12)0.0007 (14)0.0061 (9)
C1130.055 (3)0.0367 (11)0.0434 (13)0.0132 (15)0.0043 (15)0.0037 (9)
C1140.0417 (14)0.0388 (12)0.0371 (11)0.0002 (11)0.0055 (8)0.0023 (9)
C1150.051 (3)0.0383 (16)0.0394 (12)0.005 (2)0.0016 (15)0.0073 (11)
C1160.047 (3)0.0320 (13)0.0430 (13)0.0078 (18)0.0006 (14)0.0015 (10)
S1210.0628 (9)0.0437 (6)0.0379 (4)0.0019 (5)0.0022 (5)0.0094 (4)
C1220.038 (2)0.0365 (14)0.0337 (10)0.0003 (16)0.0028 (10)0.0036 (9)
C1230.039 (2)0.0393 (14)0.0340 (10)0.0002 (16)0.0017 (10)0.0001 (10)
C1240.045 (2)0.0449 (15)0.0351 (12)0.0024 (14)0.0021 (12)0.0053 (10)
C1250.061 (2)0.0515 (17)0.0357 (12)0.0066 (16)0.0011 (12)0.0019 (11)
C1260.096 (3)0.076 (3)0.0348 (15)0.007 (2)0.0049 (17)0.0089 (15)
C1270.188 (5)0.116 (4)0.061 (3)0.034 (4)0.026 (3)0.032 (2)
C1370.0413 (13)0.0398 (11)0.0343 (12)0.0030 (10)0.0041 (10)0.0019 (9)
O1370.070 (3)0.0515 (10)0.0364 (12)0.0188 (15)0.0062 (16)0.0080 (9)
C1310.0480 (14)0.0439 (12)0.0370 (11)0.0079 (10)0.0069 (12)0.0018 (9)
C1320.0507 (14)0.0647 (16)0.0369 (18)0.0097 (12)0.0018 (12)0.0008 (12)
Cl120.0577 (5)0.0824 (7)0.0845 (11)0.0191 (4)0.0036 (7)0.0109 (7)
C1330.0593 (19)0.099 (3)0.067 (4)0.0310 (18)0.0057 (17)0.005 (2)
C1340.102 (3)0.084 (3)0.101 (5)0.051 (2)0.008 (3)0.023 (3)
C1350.120 (4)0.0459 (16)0.115 (3)0.0192 (19)0.036 (3)0.0180 (18)
C1360.068 (2)0.0465 (14)0.076 (3)0.0061 (13)0.021 (2)0.0044 (13)
C1410.0490 (19)0.0407 (17)0.0357 (12)0.0056 (15)0.0032 (12)0.0064 (11)
C1420.070 (2)0.058 (3)0.0430 (19)0.011 (2)0.0003 (18)0.0055 (17)
C1430.0725 (17)0.066 (4)0.053 (2)0.006 (2)0.0123 (19)0.013 (2)
C1440.073 (3)0.0538 (16)0.0384 (16)0.024 (2)0.0051 (17)0.0122 (14)
C1450.074 (3)0.060 (2)0.0380 (14)0.017 (2)0.0091 (15)0.0025 (13)
C1460.057 (3)0.055 (2)0.0429 (13)0.003 (2)0.0062 (14)0.0006 (12)
C210.043 (2)0.0336 (11)0.0401 (12)0.0061 (12)0.0016 (12)0.0029 (9)
O210.0996 (13)0.0470 (9)0.0461 (9)0.0262 (9)0.0137 (9)0.0143 (7)
N210.049 (2)0.0364 (9)0.0334 (10)0.0076 (11)0.0008 (12)0.0053 (8)
C2110.036 (2)0.0323 (11)0.0374 (11)0.0027 (13)0.0027 (11)0.0008 (9)
C2120.056 (3)0.0357 (11)0.0405 (12)0.0113 (12)0.0007 (14)0.0061 (9)
C2130.055 (3)0.0367 (11)0.0434 (13)0.0132 (15)0.0043 (15)0.0037 (9)
C2140.0417 (14)0.0388 (12)0.0371 (11)0.0002 (11)0.0055 (8)0.0023 (9)
C2150.051 (3)0.0383 (16)0.0394 (12)0.005 (2)0.0016 (15)0.0073 (11)
C2160.047 (3)0.0320 (13)0.0430 (13)0.0078 (18)0.0006 (14)0.0015 (10)
S2210.0628 (9)0.0437 (6)0.0379 (4)0.0019 (5)0.0022 (5)0.0094 (4)
C2220.038 (2)0.0365 (14)0.0337 (10)0.0003 (16)0.0028 (10)0.0036 (9)
C2230.039 (2)0.0393 (14)0.0340 (10)0.0002 (16)0.0017 (10)0.0001 (10)
C2240.045 (2)0.0449 (15)0.0351 (12)0.0024 (14)0.0021 (12)0.0053 (10)
C2250.061 (2)0.0515 (17)0.0357 (12)0.0066 (16)0.0011 (12)0.0019 (11)
C2260.096 (3)0.076 (3)0.0348 (15)0.007 (2)0.0049 (17)0.0089 (15)
C2270.188 (5)0.116 (4)0.061 (3)0.034 (4)0.026 (3)0.032 (2)
C2370.0413 (13)0.0398 (11)0.0343 (12)0.0030 (10)0.0041 (10)0.0019 (9)
O2370.070 (3)0.0515 (10)0.0364 (12)0.0188 (15)0.0062 (16)0.0080 (9)
C2310.0480 (14)0.0439 (12)0.0370 (11)0.0079 (10)0.0069 (12)0.0018 (9)
C2320.0507 (14)0.0647 (16)0.0369 (18)0.0097 (12)0.0018 (12)0.0008 (12)
Cl220.0577 (5)0.0824 (7)0.0845 (11)0.0191 (4)0.0036 (7)0.0109 (7)
C2330.0593 (19)0.099 (3)0.067 (4)0.0310 (18)0.0057 (17)0.005 (2)
C2340.102 (3)0.084 (3)0.101 (5)0.051 (2)0.008 (3)0.023 (3)
C2350.120 (4)0.0459 (16)0.115 (3)0.0192 (19)0.036 (3)0.0180 (18)
C2360.068 (2)0.0465 (14)0.076 (3)0.0061 (13)0.021 (2)0.0044 (13)
C2410.0490 (19)0.0407 (17)0.0357 (12)0.0056 (15)0.0032 (12)0.0064 (11)
C2420.070 (2)0.058 (3)0.0430 (19)0.011 (2)0.0003 (18)0.0055 (17)
C2430.0725 (17)0.066 (4)0.053 (2)0.006 (2)0.0123 (19)0.013 (2)
C2440.073 (3)0.0538 (16)0.0384 (16)0.024 (2)0.0051 (17)0.0122 (14)
C2450.074 (3)0.060 (2)0.0380 (14)0.017 (2)0.0091 (15)0.0025 (13)
C2460.057 (3)0.055 (2)0.0429 (13)0.003 (2)0.0062 (14)0.0006 (12)
Geometric parameters (Å, º) top
C11—O111.223 (3)C21—N211.370 (5)
C11—N111.367 (3)C21—C2111.486 (5)
C11—C1111.486 (3)N21—C2221.381 (6)
N11—C1221.379 (4)N21—H210.8600
N11—H110.8600C211—C2161.391 (5)
C111—C1161.389 (3)C211—C2121.401 (6)
C111—C1121.399 (4)C212—C2131.374 (5)
C112—C1131.373 (3)C212—H2120.9300
C112—H1120.9300C213—C2141.394 (6)
C113—C1141.394 (4)C213—H2130.9300
C113—H1130.9300C214—C2151.392 (5)
C114—C1151.392 (4)C214—C2411.487 (5)
C114—C1411.487 (3)C215—C2161.383 (5)
C115—C1161.382 (3)C215—H2150.9300
C115—H1150.9300C216—H2160.9300
C116—H1160.9300S221—C2221.719 (4)
S121—C1221.718 (2)S221—C2251.748 (5)
S121—C1251.747 (3)C222—C2231.382 (5)
C122—C1231.381 (3)C223—C2241.431 (5)
C123—C1241.432 (3)C223—C2371.464 (6)
C123—C1371.463 (4)C224—C2251.341 (5)
C124—C1251.340 (3)C224—H2240.9300
C124—H1240.9300C225—C2261.511 (5)
C125—C1261.510 (3)C226—C2271.500 (7)
C126—C1271.501 (6)C226—H26A0.9700
C126—H16A0.9700C226—H26B0.9700
C126—H16B0.9700C227—H27A0.9600
C127—H17A0.9600C227—H27B0.9600
C127—H17B0.9600C227—H27C0.9600
C127—H17C0.9600C237—O2371.230 (5)
C137—O1371.228 (3)C237—C2311.506 (5)
C137—C1311.506 (3)C231—C2321.382 (5)
C131—C1321.382 (3)C231—C2361.387 (5)
C131—C1361.387 (4)C232—C2331.380 (5)
C132—C1331.380 (4)C232—Cl221.739 (5)
C132—Cl121.741 (3)C233—C2341.358 (6)
C133—C1341.358 (5)C233—H2330.9300
C133—H1330.9300C234—C2351.374 (7)
C134—C1351.375 (5)C234—H2340.9300
C134—H1340.9300C235—C2361.388 (6)
C135—C1361.388 (4)C235—H2350.9300
C135—H1350.9300C236—H2360.9300
C136—H1360.9300C241—C2461.385 (5)
C141—C1461.385 (3)C241—C2421.392 (7)
C141—C1421.392 (4)C242—C2431.386 (5)
C142—C1431.385 (4)C242—H2420.9300
C142—H1420.9300C243—C2441.370 (8)
C143—C1441.370 (6)C243—H2430.9300
C143—H1430.9300C244—C2451.364 (6)
C144—C1451.363 (4)C244—H2440.9300
C144—H1440.9300C245—C2461.392 (5)
C145—C1461.391 (4)C245—H2450.9300
C145—H1450.9300C246—H2460.9300
C146—H1460.9300
O11—C11—N11119.8 (2)C145—C146—H146119.3
O11—C11—C111123.3 (2)N21—C21—C211116.1 (7)
N11—C11—C111116.8 (2)C21—N21—C222124.1 (8)
C11—N11—C122125.2 (2)C21—N21—H21118.0
C11—N11—H11117.4C222—N21—H21118.0
C122—N11—H11117.4C216—C211—C212117.6 (9)
C116—C111—C112118.0 (2)C216—C211—C21123.8 (7)
C116—C111—C11124.2 (2)C212—C211—C21117.4 (7)
C112—C111—C11117.7 (2)C213—C212—C211120.0 (7)
C113—C112—C111120.6 (2)C213—C212—H212120.0
C113—C112—H112119.7C211—C212—H212120.0
C111—C112—H112119.7C212—C213—C214121.4 (7)
C112—C113—C114121.7 (2)C212—C213—H213119.3
C112—C113—H113119.1C214—C213—H213119.3
C114—C113—H113119.1C215—C214—C213117.5 (6)
C115—C114—C113117.4 (2)C215—C214—C241121.1 (8)
C115—C114—C141121.1 (2)C213—C214—C241121.4 (6)
C113—C114—C141121.5 (2)C216—C215—C214120.9 (6)
C116—C115—C114121.3 (3)C216—C215—H215119.5
C116—C115—H115119.3C214—C215—H215119.5
C114—C115—H115119.3C215—C216—C211120.3 (6)
C115—C116—C111120.9 (2)C215—C216—H216119.8
C115—C116—H116119.5C211—C216—H216119.8
C111—C116—H116119.5C222—S221—C22591.3 (3)
C122—S121—C12591.49 (12)N21—C222—C223123.5 (7)
N11—C122—C123124.1 (2)N21—C222—S221123.5 (7)
N11—C122—S121123.93 (18)C223—C222—S221112.1 (4)
C123—C122—S121111.91 (17)C222—C223—C224111.0 (4)
C122—C123—C124111.4 (2)C222—C223—C237121.5 (7)
C122—C123—C137122.3 (2)C224—C223—C237127.0 (8)
C124—C123—C137126.3 (2)C225—C224—C223114.2 (5)
C125—C124—C123114.1 (2)C225—C224—H224122.9
C125—C124—H124123.0C223—C224—H224122.9
C123—C124—H124123.0C224—C225—C226128.5 (7)
C124—C125—C126129.3 (3)C224—C225—S221111.0 (4)
C124—C125—S121111.17 (18)C226—C225—S221119.7 (6)
C126—C125—S121119.5 (2)C227—C226—C225113.2 (8)
C127—C126—C125113.2 (3)C227—C226—H26A108.9
C127—C126—H16A108.9C225—C226—H26A108.9
C125—C126—H16A108.9C227—C226—H26B108.9
C127—C126—H16B108.9C225—C226—H26B108.9
C125—C126—H16B108.9H26A—C226—H26B107.7
H16A—C126—H16B107.8C226—C227—H27A109.5
C126—C127—H17A109.5C226—C227—H27B109.5
C126—C127—H17B109.5H27A—C227—H27B109.5
H17A—C127—H17B109.5C226—C227—H27C109.5
C126—C127—H17C109.5H27A—C227—H27C109.5
H17A—C127—H17C109.5H27B—C227—H27C109.5
H17B—C127—H17C109.5O237—C237—C223122.0 (8)
O137—C137—C123122.7 (2)O237—C237—C231118.4 (7)
O137—C137—C131118.9 (2)C223—C237—C231118.7 (6)
C123—C137—C131118.3 (2)C232—C231—C236118.5 (5)
C132—C131—C136118.8 (2)C232—C231—C237122.1 (6)
C132—C131—C137122.2 (2)C236—C231—C237119.0 (6)
C136—C131—C137119.0 (2)C233—C232—C231121.4 (6)
C133—C132—C131121.3 (3)C233—C232—Cl22118.6 (6)
C133—C132—Cl12118.6 (2)C231—C232—Cl22120.0 (6)
C131—C132—Cl12120.0 (2)C234—C233—C232119.3 (6)
C134—C133—C132119.4 (3)C234—C233—H233120.3
C134—C133—H133120.3C232—C233—H233120.3
C132—C133—H133120.3C233—C234—C235120.7 (6)
C133—C134—C135120.8 (3)C233—C234—H234119.7
C133—C134—H134119.6C235—C234—H234119.7
C135—C134—H134119.6C234—C235—C236120.2 (6)
C134—C135—C136120.2 (3)C234—C235—H235119.9
C134—C135—H135119.9C236—C235—H235119.9
C136—C135—H135119.9C231—C236—C235119.7 (6)
C131—C136—C135119.6 (3)C231—C236—H236120.1
C131—C136—H136120.2C235—C236—H236120.1
C135—C136—H136120.2C246—C241—C242117.4 (6)
C146—C141—C142117.3 (2)C246—C241—C214121.6 (7)
C146—C141—C114121.9 (2)C242—C241—C214120.6 (7)
C142—C141—C114120.7 (3)C243—C242—C241120.8 (6)
C143—C142—C141121.1 (4)C243—C242—H242119.6
C143—C142—H142119.4C241—C242—H242119.6
C141—C142—H142119.4C244—C243—C242119.6 (10)
C144—C143—C142120.2 (4)C244—C243—H243120.2
C144—C143—H143119.9C242—C243—H243120.2
C142—C143—H143119.9C245—C244—C243119.7 (8)
C145—C144—C143120.1 (3)C245—C244—H244120.1
C145—C144—H144120.0C243—C244—H244119
C143—C144—H144120.0C244—C245—C246119.4 (7)
C144—C145—C146119.9 (3)C244—C245—H245120.3
C144—C145—H145120.1C246—C245—H245120.3
C146—C145—H145120.1C241—C246—C245121.2 (6)
C141—C146—C145121.5 (3)C241—C246—H246119.4
C141—C146—H146119.3C245—C246—H246119.4
O11—C11—N11—C1223.8 (14)C144—C145—C146—C1410.1 (12)
C111—C11—N11—C122179.1 (11)C211—C21—N21—C222163 (6)
O11—C11—C111—C116175.0 (9)N21—C21—C211—C21610 (6)
N11—C11—C111—C1161.9 (10)N21—C21—C211—C212157 (5)
O11—C11—C111—C1122.1 (10)C216—C211—C212—C21316 (6)
N11—C11—C111—C112179.1 (9)C21—C211—C212—C213177 (4)
C116—C111—C112—C1131.0 (10)C211—C212—C213—C2145 (7)
C11—C111—C112—C113178.3 (6)C212—C213—C214—C2157 (8)
C111—C112—C113—C1140.6 (12)C212—C213—C214—C241170 (4)
C112—C113—C114—C1150.5 (16)C213—C214—C215—C2168 (10)
C112—C113—C114—C141178.1 (7)C241—C214—C215—C216169 (7)
C113—C114—C115—C1160.8 (18)C214—C215—C216—C2113 (10)
C141—C114—C115—C116177.7 (12)C212—C211—C216—C21515 (8)
C114—C115—C116—C1111.3 (19)C21—C211—C216—C215178 (6)
C112—C111—C116—C1151.4 (14)C21—N21—C222—C223178 (5)
C11—C111—C116—C115178.5 (11)C21—N21—C222—S22114 (8)
C11—N11—C122—C123171.9 (10)C225—S221—C222—N21169 (4)
C11—N11—C122—S1216.3 (15)C225—S221—C222—C2231 (4)
C125—S121—C122—N11179.5 (8)N21—C222—C223—C224172 (5)
C125—S121—C122—C1231.0 (6)S221—C222—C223—C2242 (5)
N11—C122—C123—C124179.3 (8)N21—C222—C223—C2370 (7)
S121—C122—C123—C1240.9 (8)S221—C222—C223—C237170 (4)
N11—C122—C123—C1371.9 (13)C222—C223—C224—C2255 (5)
S121—C122—C123—C137176.6 (6)C237—C223—C224—C225166 (4)
C122—C123—C124—C1250.2 (8)C223—C224—C225—C226176 (3)
C137—C123—C124—C125177.1 (6)C223—C224—C225—S2216 (4)
C123—C124—C125—C126178.4 (5)C222—S221—C225—C2244 (3)
C123—C124—C125—S1210.5 (6)C222—S221—C225—C226175 (3)
C122—S121—C125—C1240.9 (4)C224—C225—C226—C227142 (3)
C122—S121—C125—C126178.2 (4)S221—C225—C226—C22749 (3)
C124—C125—C126—C127125.9 (5)C222—C223—C237—O2373 (6)
S121—C125—C126—C12755.2 (5)C224—C223—C237—O237174 (4)
C122—C123—C137—O13711.7 (11)C222—C223—C237—C231172 (3)
C124—C123—C137—O137171.3 (7)C224—C223—C237—C23117 (6)
C122—C123—C137—C131171.0 (6)O237—C237—C231—C232104 (4)
C124—C123—C137—C1316.0 (10)C223—C237—C231—C23265 (3)
O137—C137—C131—C132113.7 (7)O237—C237—C231—C23669 (4)
C123—C137—C131—C13268.8 (7)C223—C237—C231—C236121 (3)
O137—C137—C131—C13663.6 (7)C236—C231—C232—C2335 (3)
C123—C137—C131—C136113.8 (6)C237—C231—C232—C233178 (2)
C136—C131—C132—C1330.3 (6)C236—C231—C232—Cl22177.6 (19)
C137—C131—C132—C133177.1 (4)C237—C231—C232—Cl224 (2)
C136—C131—C132—Cl12176.6 (4)C231—C232—C233—C2345 (4)
C137—C131—C132—Cl120.7 (5)Cl22—C232—C233—C234177 (3)
C131—C132—C133—C1341.2 (8)C232—C233—C234—C2352 (6)
Cl12—C132—C133—C134177.5 (6)C233—C234—C235—C2362 (7)
C132—C133—C134—C1350.6 (12)C232—C231—C236—C2351 (4)
C133—C134—C135—C1360.8 (13)C237—C231—C236—C235175 (4)
C132—C131—C136—C1351.1 (9)C234—C235—C236—C2312 (6)
C137—C131—C136—C135178.6 (7)C215—C214—C241—C24641 (7)
C134—C135—C136—C1311.7 (12)C213—C214—C241—C246142 (7)
C115—C114—C141—C14631.7 (13)C215—C214—C241—C242147 (8)
C113—C114—C141—C146149.9 (13)C213—C214—C241—C24230 (8)
C115—C114—C141—C142145.2 (16)C246—C241—C242—C2434 (12)
C113—C114—C141—C14233.3 (16)C214—C241—C242—C243177 (7)
C146—C141—C142—C1431 (2)C241—C242—C243—C2446 (12)
C114—C141—C142—C143177.7 (13)C242—C243—C244—C24516 (9)
C141—C142—C143—C1441 (2)C243—C244—C245—C24614 (6)
C142—C143—C144—C1452.0 (16)C242—C241—C246—C2457 (9)
C143—C144—C145—C1461.6 (10)C214—C241—C246—C245179 (4)
C142—C141—C146—C1451.2 (16)C244—C245—C246—C2412 (7)
C114—C141—C146—C145178.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1370.862.082.719 (10)130
N21—H21···O2370.862.012.65 (5)131
C112—H112···O11i0.932.473.230 (4)139
C144—H144···O137ii0.932.563.397 (6)150
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1/2, z+3/2.
2-Bromo-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide (III) top
Crystal data top
C20H15BrClNO2SF(000) = 1808
Mr = 448.74Dx = 1.568 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 18.8096 (10) ÅCell parameters from 4009 reflections
b = 11.5021 (7) Åθ = 2.2–26.8°
c = 19.9112 (11) ŵ = 2.43 mm1
β = 118.030 (2)°T = 294 K
V = 3802.5 (4) Å3Block, yellow
Z = 80.25 × 0.20 × 0.10 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2370 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.047
φ and ω scansθmax = 26.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 2323
Tmin = 0.614, Tmax = 0.785k = 1414
25510 measured reflectionsl = 2425
4009 independent reflections
Refinement top
Refinement on F264 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0522P)2 + 2.9782P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4009 reflectionsΔρmax = 0.40 e Å3
322 parametersΔρmin = 0.50 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.5823 (3)0.5906 (4)0.4593 (4)0.0496 (13)0.7006 (12)
O110.5148 (4)0.5810 (7)0.4072 (8)0.0687 (16)0.7006 (12)
N110.6219 (6)0.4975 (5)0.5055 (8)0.0482 (17)0.7006 (12)
H110.66720.51180.54480.058*0.7006 (12)
C1110.6254 (3)0.7051 (3)0.4898 (3)0.0469 (11)0.7006 (12)
C1120.6211 (3)0.7899 (4)0.4387 (3)0.0614 (12)0.7006 (12)
C1130.6670 (4)0.8934 (5)0.4679 (5)0.0871 (18)0.7006 (12)
H1130.66440.95220.43480.105*0.7006 (12)
C1140.7141 (3)0.9067 (5)0.5434 (4)0.0749 (16)0.7006 (12)
H1140.74430.97430.56150.090*0.7006 (12)
C1150.7185 (3)0.8245 (4)0.5931 (3)0.0747 (14)0.7006 (12)
H1150.75120.83570.64500.090*0.7006 (12)
C1160.6745 (3)0.7236 (4)0.5671 (4)0.0559 (12)0.7006 (12)
H1160.67770.66710.60180.067*0.7006 (12)
S1210.5058 (4)0.3394 (6)0.4205 (4)0.0503 (10)0.7006 (12)
C1220.5958 (8)0.3838 (5)0.4946 (8)0.042 (2)0.7006 (12)
C1230.6416 (7)0.2913 (6)0.5371 (8)0.0467 (15)0.7006 (12)
C1240.5995 (6)0.1840 (5)0.5103 (6)0.0467 (15)0.7006 (12)
H1240.61900.11350.53510.056*0.7006 (12)
C1250.5291 (10)0.1936 (6)0.4460 (12)0.0523 (9)0.7006 (12)
C1260.4719 (10)0.0994 (9)0.3996 (10)0.0660 (10)0.7006 (12)
H16A0.42170.10880.40150.079*0.7006 (12)
H16B0.49450.02470.42200.079*0.7006 (12)
C1270.4548 (12)0.100 (2)0.3178 (9)0.120 (6)0.7006 (12)
H17A0.50470.09730.31560.180*0.7006 (12)
H17B0.42600.16920.29340.180*0.7006 (12)
H17C0.42290.03300.29230.180*0.7006 (12)
C1370.7199 (5)0.3072 (6)0.6033 (5)0.0491 (11)0.7006 (12)
O1370.7551 (8)0.4013 (6)0.6196 (11)0.0694 (13)0.7006 (12)
C1310.7633 (5)0.2024 (7)0.6494 (6)0.0459 (13)0.7006 (12)
C1320.7380 (10)0.1439 (15)0.695 (2)0.0590 (12)0.7006 (12)
Cl120.6507 (7)0.1871 (8)0.6970 (8)0.0916 (12)0.7006 (12)
C1330.7822 (13)0.050 (2)0.7400 (16)0.0754 (17)0.7006 (12)
H1330.76420.00920.76940.090*0.7006 (12)
C1340.8519 (13)0.020 (2)0.7397 (17)0.0838 (16)0.7006 (12)
H1340.88290.04020.77100.101*0.7006 (12)
C1350.8777 (13)0.076 (2)0.6946 (19)0.080 (3)0.7006 (12)
H1350.92400.05070.69330.096*0.7006 (12)
C1360.8354 (12)0.170 (2)0.6510 (17)0.063 (2)0.7006 (12)
H1360.85490.21080.62280.076*0.7006 (12)
Br120.56130 (4)0.7721 (7)0.33313 (4)0.0997 (3)0.7006 (12)
C210.5651 (9)0.5994 (9)0.4558 (8)0.0496 (13)0.2994 (12)
O210.4990 (12)0.5722 (17)0.4048 (19)0.0687 (16)0.2994 (12)
N210.6193 (14)0.5109 (11)0.494 (2)0.0482 (17)0.2994 (12)
H210.66830.52920.52500.058*0.2994 (12)
C2110.6065 (7)0.7113 (8)0.4527 (5)0.0469 (11)0.2994 (12)
C2120.5735 (6)0.7690 (8)0.3833 (6)0.0614 (12)0.2994 (12)
H2120.53020.73780.34060.074*0.2994 (12)
C2130.6082 (6)0.878 (2)0.3795 (7)0.0871 (18)0.2994 (12)
H2130.59380.91260.33260.105*0.2994 (12)
C2140.6616 (8)0.9299 (9)0.4440 (7)0.0749 (16)0.2994 (12)
H2140.68061.00360.44150.090*0.2994 (12)
C2150.6883 (10)0.8782 (10)0.5119 (7)0.0747 (14)0.2994 (12)
H2150.72450.91710.55560.090*0.2994 (12)
C2160.6627 (6)0.7681 (8)0.5178 (6)0.0559 (12)0.2994 (12)
S2210.5091 (11)0.345 (2)0.4115 (10)0.0503 (10)0.2994 (12)
C2220.5979 (19)0.3948 (10)0.485 (2)0.042 (2)0.2994 (12)
C2230.6420 (16)0.3068 (10)0.5338 (18)0.043 (4)0.2994 (12)
C2240.6063 (14)0.1960 (10)0.505 (2)0.0467 (15)0.2994 (12)
H2240.63260.12590.52410.056*0.2994 (12)
C2250.531 (2)0.2026 (14)0.446 (3)0.0523 (9)0.2994 (12)
C2260.475 (2)0.1052 (19)0.404 (2)0.0660 (10)0.2994 (12)
H26A0.43450.09830.42070.079*0.2994 (12)
H26B0.50480.03300.41540.079*0.2994 (12)
C2270.433 (3)0.123 (5)0.319 (2)0.120 (6)0.2994 (12)
H27A0.40240.05450.29420.180*0.2994 (12)
H27B0.47240.13630.30190.180*0.2994 (12)
H27C0.39760.18850.30600.180*0.2994 (12)
C2370.7215 (12)0.327 (2)0.5976 (13)0.0491 (11)0.2994 (12)
O2370.751 (2)0.4247 (17)0.616 (3)0.0694 (13)0.2994 (12)
C2310.7665 (11)0.226 (2)0.6470 (14)0.0459 (13)0.2994 (12)
C2320.737 (2)0.162 (4)0.688 (3)0.0590 (12)0.2994 (12)
Cl220.6515 (17)0.209 (2)0.6916 (19)0.0916 (12)0.2994 (12)
C2330.782 (3)0.070 (5)0.734 (4)0.0754 (17)0.2994 (12)
H2330.76500.03210.76560.090*0.2994 (12)
C2340.850 (3)0.035 (5)0.731 (4)0.0838 (16)0.2994 (12)
H2340.87660.03090.75800.101*0.2994 (12)
C2350.879 (3)0.096 (5)0.691 (4)0.080 (3)0.2994 (12)
H2350.92750.07350.69280.096*0.2994 (12)
C2360.837 (3)0.189 (5)0.646 (4)0.063 (2)0.2994 (12)
H2360.85520.22700.61640.076*0.2994 (12)
Br260.70489 (8)0.7080 (2)0.61638 (8)0.0658 (5)0.2994 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.039 (3)0.0408 (19)0.074 (2)0.0098 (19)0.030 (2)0.0003 (17)
O110.044 (3)0.0569 (18)0.0816 (18)0.0024 (16)0.010 (3)0.0079 (17)
N110.0462 (15)0.0374 (19)0.051 (5)0.0027 (15)0.0141 (17)0.0005 (18)
C1110.045 (3)0.0412 (19)0.055 (3)0.0048 (19)0.023 (3)0.001 (3)
C1120.053 (3)0.049 (3)0.090 (4)0.002 (2)0.040 (2)0.006 (3)
C1130.087 (4)0.056 (3)0.143 (5)0.020 (3)0.074 (5)0.030 (4)
C1140.056 (3)0.049 (3)0.120 (5)0.001 (2)0.042 (3)0.013 (3)
C1150.069 (3)0.052 (3)0.095 (4)0.004 (2)0.030 (3)0.018 (3)
C1160.050 (3)0.047 (3)0.060 (4)0.001 (2)0.016 (3)0.005 (2)
S1210.0446 (7)0.0471 (8)0.0521 (18)0.0037 (5)0.0170 (10)0.0004 (9)
C1220.0428 (16)0.0407 (19)0.045 (4)0.0039 (18)0.022 (2)0.0008 (18)
C1230.052 (2)0.0352 (17)0.054 (2)0.0015 (15)0.0254 (18)0.0012 (15)
C1240.052 (2)0.0352 (17)0.054 (2)0.0015 (15)0.0254 (18)0.0012 (15)
C1250.0529 (19)0.044 (2)0.0585 (19)0.0060 (18)0.0246 (16)0.008 (2)
C1260.059 (2)0.053 (2)0.077 (3)0.0120 (18)0.0243 (19)0.0149 (19)
C1270.168 (13)0.079 (11)0.065 (3)0.043 (9)0.016 (6)0.018 (4)
C1370.0540 (18)0.040 (3)0.049 (2)0.0018 (19)0.0205 (16)0.001 (2)
O1370.060 (2)0.036 (3)0.079 (2)0.005 (3)0.0047 (14)0.000 (4)
C1310.0516 (18)0.038 (4)0.0402 (17)0.004 (2)0.0151 (14)0.002 (2)
C1320.073 (2)0.051 (6)0.053 (4)0.003 (3)0.030 (2)0.000 (3)
Cl120.1105 (8)0.088 (4)0.113 (2)0.002 (2)0.0822 (10)0.004 (2)
C1330.106 (3)0.060 (8)0.056 (5)0.009 (4)0.035 (3)0.010 (4)
C1340.090 (3)0.069 (7)0.058 (7)0.014 (3)0.006 (4)0.021 (3)
C1350.059 (2)0.080 (9)0.080 (4)0.017 (5)0.017 (2)0.016 (5)
C1360.053 (2)0.061 (8)0.062 (4)0.010 (4)0.0158 (18)0.009 (4)
Br120.1039 (5)0.1178 (6)0.0784 (5)0.0125 (4)0.0437 (4)0.0350 (4)
C210.039 (3)0.0408 (19)0.074 (2)0.0098 (19)0.030 (2)0.0003 (17)
O210.044 (3)0.0569 (18)0.0816 (18)0.0024 (16)0.010 (3)0.0079 (17)
N210.0462 (15)0.0374 (19)0.051 (5)0.0027 (15)0.0141 (17)0.0005 (18)
C2110.045 (3)0.0412 (19)0.055 (3)0.0048 (19)0.023 (3)0.001 (3)
C2120.053 (3)0.049 (3)0.090 (4)0.002 (2)0.040 (2)0.006 (3)
C2130.087 (4)0.056 (3)0.143 (5)0.020 (3)0.074 (5)0.030 (4)
C2140.056 (3)0.049 (3)0.120 (5)0.001 (2)0.042 (3)0.013 (3)
C2150.069 (3)0.052 (3)0.095 (4)0.004 (2)0.030 (3)0.018 (3)
C2160.050 (3)0.047 (3)0.060 (4)0.001 (2)0.016 (3)0.005 (2)
S2210.0446 (7)0.0471 (8)0.0521 (18)0.0037 (5)0.0170 (10)0.0004 (9)
C2220.0428 (16)0.0407 (19)0.045 (4)0.0039 (18)0.022 (2)0.0008 (18)
C2230.039 (6)0.035 (7)0.037 (7)0.002 (6)0.003 (5)0.005 (7)
C2240.052 (2)0.0352 (17)0.054 (2)0.0015 (15)0.0254 (18)0.0012 (15)
C2250.0529 (19)0.044 (2)0.0585 (19)0.0060 (18)0.0246 (16)0.008 (2)
C2260.059 (2)0.053 (2)0.077 (3)0.0120 (18)0.0243 (19)0.0149 (19)
C2270.168 (13)0.079 (11)0.065 (3)0.043 (9)0.016 (6)0.018 (4)
C2370.0540 (18)0.040 (3)0.049 (2)0.0018 (19)0.0205 (16)0.001 (2)
O2370.060 (2)0.036 (3)0.079 (2)0.005 (3)0.0047 (14)0.000 (4)
C2310.0516 (18)0.038 (4)0.0402 (17)0.004 (2)0.0151 (14)0.002 (2)
C2320.073 (2)0.051 (6)0.053 (4)0.003 (3)0.030 (2)0.000 (3)
Cl220.1105 (8)0.088 (4)0.113 (2)0.002 (2)0.0822 (10)0.004 (2)
C2330.106 (3)0.060 (8)0.056 (5)0.009 (4)0.035 (3)0.010 (4)
C2340.090 (3)0.069 (7)0.058 (7)0.014 (3)0.006 (4)0.021 (3)
C2350.059 (2)0.080 (9)0.080 (4)0.017 (5)0.017 (2)0.016 (5)
C2360.053 (2)0.061 (8)0.062 (4)0.010 (4)0.0158 (18)0.009 (4)
Br260.0641 (8)0.0600 (8)0.0514 (8)0.0015 (6)0.0090 (6)0.0028 (6)
Geometric parameters (Å, º) top
C11—O111.209 (4)C21—O211.219 (5)
C11—N111.380 (5)C21—N211.388 (6)
C11—C1111.516 (5)C21—C2111.521 (7)
N11—C1221.377 (4)N21—C2221.382 (5)
N11—H110.8600N21—H210.8600
C111—C1121.384 (6)C211—C2121.388 (7)
C111—C1161.391 (7)C211—C2161.391 (8)
C112—C1131.425 (8)C212—C2131.432 (9)
C112—Br121.871 (6)C212—H2120.9300
C113—C1141.347 (9)C213—C2141.343 (10)
C113—H1130.9300C213—H2130.9300
C114—C1151.342 (8)C214—C2151.341 (9)
C114—H1140.9300C214—H2140.9300
C115—C1161.377 (6)C215—C2161.380 (7)
C115—H1150.9300C215—H2150.9300
C116—H1160.9300C216—Br261.870 (10)
S121—C1221.720 (3)S221—C2221.721 (4)
S121—C1251.747 (4)S221—C2251.748 (6)
C122—C1231.380 (5)C222—C2231.378 (6)
C123—C1241.428 (5)C223—C2241.430 (6)
C123—C1371.454 (5)C223—C2371.455 (6)
C124—C1251.345 (5)C224—C2251.346 (7)
C124—H1240.9300C224—H2240.9300
C125—C1261.500 (4)C225—C2261.501 (5)
C126—C1271.504 (9)C226—C2271.504 (9)
C126—H16A0.9700C226—H26A0.9700
C126—H16B0.9700C226—H26B0.9700
C127—H17A0.9600C227—H27A0.9600
C127—H17B0.9600C227—H27B0.9600
C127—H17C0.9600C227—H27C0.9600
C137—O1371.231 (5)C237—O2371.230 (6)
C137—C1311.502 (4)C237—C2311.502 (5)
C131—C1321.382 (5)C231—C2321.382 (6)
C131—C1361.394 (4)C231—C2361.394 (6)
C132—C1331.398 (5)C232—C2331.399 (6)
C132—Cl121.734 (4)C232—Cl221.734 (5)
C133—C1341.360 (6)C233—C2341.360 (7)
C133—H1330.9300C233—H2330.9300
C134—C1351.365 (7)C234—C2351.365 (8)
C134—H1340.9300C234—H2340.9300
C135—C1361.379 (5)C235—C2361.379 (6)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O11—C11—N11121.4 (3)O21—C21—N21117.9 (8)
O11—C11—C111124.8 (4)O21—C21—C211121.6 (9)
N11—C11—C111112.8 (4)N21—C21—C211112.6 (8)
C122—N11—C11126.2 (4)C222—N21—C21122.9 (8)
C122—N11—H11116.9C222—N21—H21118.6
C11—N11—H11116.9C21—N21—H21118.6
C112—C111—C116119.0 (4)C212—C211—C216119.4 (6)
C112—C111—C11118.8 (5)C212—C211—C21116.6 (6)
C116—C111—C11122.0 (4)C216—C211—C21122.6 (7)
C111—C112—C113118.3 (5)C211—C212—C213118.1 (7)
C111—C112—Br12123.0 (3)C211—C212—H212121.0
C113—C112—Br12118.6 (4)C213—C212—H212121.0
C114—C113—C112120.3 (5)C214—C213—C212119.5 (7)
C114—C113—H113119.8C214—C213—H213120.2
C112—C113—H113119.8C212—C213—H213120.2
C115—C114—C113121.5 (5)C215—C214—C213121.7 (7)
C115—C114—H114119.3C215—C214—H214119.2
C113—C114—H114119.3C213—C214—H214119.2
C114—C115—C116119.9 (5)C214—C215—C216120.9 (8)
C114—C115—H115120.0C214—C215—H215119.6
C116—C115—H115120.0C216—C215—H215119.6
C115—C116—C111121.0 (6)C215—C216—C211119.6 (8)
C115—C116—H116119.5C215—C216—Br26115.8 (7)
C111—C116—H116119.5C211—C216—Br26124.5 (6)
C122—S121—C12591.37 (19)C222—S221—C22591.2 (3)
N11—C122—C123124.2 (4)C223—C222—N21125.1 (6)
N11—C122—S121123.4 (3)C223—C222—S221112.1 (4)
C123—C122—S121112.1 (3)N21—C222—S221122.7 (5)
C122—C123—C124111.1 (3)C222—C223—C224110.8 (6)
C122—C123—C137122.2 (4)C222—C223—C237122.0 (7)
C124—C123—C137126.5 (4)C224—C223—C237126.1 (7)
C125—C124—C123114.1 (3)C225—C224—C223113.8 (6)
C125—C124—H124122.9C225—C224—H224123.1
C123—C124—H124122.9C223—C224—H224123.1
C124—C125—C126128.8 (3)C224—C225—C226128.5 (8)
C124—C125—S121110.9 (3)C224—C225—S221110.6 (7)
C126—C125—S121120.3 (3)C226—C225—S221120.2 (6)
C125—C126—C127113.1 (5)C225—C226—C227113.0 (7)
C125—C126—H16A109.0C225—C226—H26A109.0
C127—C126—H16A109.0C227—C226—H26A109.0
C125—C126—H16B109.0C225—C226—H26B109.0
C127—C126—H16B109.0C227—C226—H26B109.0
H16A—C126—H16B107.8H26A—C226—H26B107.8
C126—C127—H17A109.5C226—C227—H27A109.5
C126—C127—H17B109.5C226—C227—H27B109.5
H17A—C127—H17B109.5H27A—C227—H27B109.5
C126—C127—H17C109.5C226—C227—H27C109.5
H17A—C127—H17C109.5H27A—C227—H27C109.5
H17B—C127—H17C109.5H27B—C227—H27C109.5
O137—C137—C123122.7 (4)O237—C237—C223122.5 (7)
O137—C137—C131118.3 (3)O237—C237—C231118.5 (6)
C123—C137—C131118.8 (3)C223—C237—C231118.7 (6)
C132—C131—C136119.0 (4)C232—C231—C236119.0 (6)
C132—C131—C137122.4 (3)C232—C231—C237122.5 (6)
C136—C131—C137118.3 (3)C236—C231—C237118.3 (6)
C131—C132—C133120.8 (4)C231—C232—C233120.7 (7)
C131—C132—Cl12119.8 (3)C231—C232—Cl22119.8 (7)
C133—C132—Cl12119.4 (3)C233—C232—Cl22119.1 (6)
C134—C133—C132118.6 (4)C234—C233—C232118.5 (6)
C134—C133—H133120.7C234—C233—H233120.8
C132—C133—H133120.7C232—C233—H233120.8
C133—C134—C135121.6 (4)C233—C234—C235121.6 (8)
C133—C134—H134119.2C233—C234—H234118
C135—C134—H134119.2C235—C234—H234121
C134—C135—C136120.3 (4)C234—C235—C236120.3 (7)
C134—C135—H135119.9C234—C235—H235119.8
C136—C135—H135119.9C236—C235—H235119.8
C135—C136—C131119.6 (4)C235—C236—C231119.5 (6)
C135—C136—H136120.2C235—C236—H236120.2
C131—C136—H136120.2C231—C236—H236120.2
O11—C11—N11—C1228 (2)O21—C21—N21—C22210 (6)
C111—C11—N11—C122176.9 (18)C211—C21—N21—C222159 (4)
O11—C11—C111—C11244.1 (13)O21—C21—C211—C21212 (3)
N11—C11—C111—C112146.9 (10)N21—C21—C211—C212136 (2)
O11—C11—C111—C116141.4 (12)O21—C21—C211—C216154 (3)
N11—C11—C111—C11627.5 (10)N21—C21—C211—C21658 (3)
C116—C111—C112—C1130.5 (7)C216—C211—C212—C2139.8 (18)
C11—C111—C112—C113175.1 (5)C21—C211—C212—C213176.5 (12)
C116—C111—C112—Br12176.8 (4)C211—C212—C213—C21410.7 (17)
C11—C111—C112—Br122.3 (6)C212—C213—C214—C2155 (2)
C111—C112—C113—C1141.0 (8)C213—C214—C215—C2161 (3)
Br12—C112—C113—C114176.5 (4)C214—C215—C216—C2112 (3)
C112—C113—C114—C1151.0 (9)C214—C215—C216—Br26179.8 (15)
C113—C114—C115—C1160.4 (8)C212—C211—C216—C2154 (2)
C114—C115—C116—C1110.1 (7)C21—C211—C216—C215169.5 (15)
C112—C111—C116—C1150.0 (7)C212—C211—C216—Br26173.8 (9)
C11—C111—C116—C115174.4 (5)C21—C211—C216—Br267.9 (18)
C11—N11—C122—C123172.1 (19)C21—N21—C222—C223163 (5)
C11—N11—C122—S1212 (3)C21—N21—C222—S22114 (8)
C125—S121—C122—N11174 (2)C225—S221—C222—C2230 (5)
C125—S121—C122—C1230 (2)C225—S221—C222—N21178 (5)
N11—C122—C123—C124177.5 (19)N21—C222—C223—C224175 (5)
S121—C122—C123—C1243 (2)S221—C222—C223—C2247 (5)
N11—C122—C123—C1376 (3)N21—C222—C223—C2376 (8)
S121—C122—C123—C137179.4 (16)S221—C222—C223—C237176 (4)
C122—C123—C124—C1256 (2)C222—C223—C224—C22513 (6)
C137—C123—C124—C125178 (2)C237—C223—C224—C225179 (5)
C123—C124—C125—C126176 (2)C223—C224—C225—C226177 (5)
C123—C124—C125—S1216 (3)C223—C224—C225—S22113 (6)
C122—S121—C125—C1244 (2)C222—S221—C225—C2247 (5)
C122—S121—C125—C126178 (2)C222—S221—C225—C226178 (5)
C124—C125—C126—C127124 (3)C224—C225—C226—C227136 (7)
S121—C125—C126—C12759 (2)S221—C225—C226—C22733 (6)
C122—C123—C137—O13710 (3)C222—C223—C237—O2377 (8)
C124—C123—C137—O137174 (2)C224—C223—C237—O237174 (5)
C122—C123—C137—C131176.0 (16)C222—C223—C237—C231178 (4)
C124—C123—C137—C1310 (2)C224—C223—C237—C23111 (5)
O137—C137—C131—C132115 (2)O237—C237—C231—C232113 (6)
C123—C137—C131—C13271.2 (19)C223—C237—C231—C23261 (5)
O137—C137—C131—C13660 (2)O237—C237—C231—C23672 (6)
C123—C137—C131—C136114 (2)C223—C237—C231—C236113 (5)
C136—C131—C132—C1333 (4)C236—C231—C232—C2336 (9)
C137—C131—C132—C133177 (2)C237—C231—C232—C233179 (5)
C136—C131—C132—Cl12177 (2)C236—C231—C232—Cl22178 (5)
C137—C131—C132—Cl123 (3)C237—C231—C232—Cl227 (6)
C131—C132—C133—C1342 (4)C231—C232—C233—C2347 (11)
Cl12—C132—C133—C134178 (3)Cl22—C232—C233—C234179 (7)
C132—C133—C134—C1353 (5)C232—C233—C234—C2356 (13)
C133—C134—C135—C1364 (6)C233—C234—C235—C2365 (15)
C134—C135—C136—C1314 (6)C234—C235—C236—C2314 (14)
C132—C131—C136—C1354 (4)C232—C231—C236—C2355 (11)
C137—C131—C136—C135178 (3)C237—C231—C236—C235179 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1370.862.062.70 (2)131
N21—H21···O2370.862.122.71 (6)126
C114—H114···Cg1i0.932.823.565 (12)138
C214—H214···O237ii0.932.242.96 (4)134
Symmetry codes: (i) x, y+1, z; (ii) x+3/2, y+3/2, z+1.
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-2-iodobenzamide (IV) top
Crystal data top
C20H15ClINO2SF(000) = 976
Mr = 495.74Dx = 1.695 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.1813 (6) ÅCell parameters from 3860 reflections
b = 11.8276 (7) Åθ = 2.6–26.1°
c = 20.1347 (12) ŵ = 1.91 mm1
β = 94.388 (2)°T = 294 K
V = 1942.6 (2) Å3Block, yellow
Z = 40.16 × 0.14 × 0.11 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2525 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.034
φ and ω scansθmax = 26.1°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.722, Tmax = 0.811k = 1414
20297 measured reflectionsl = 2424
3860 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0549P)2 + 3.2004P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3860 reflectionsΔρmax = 0.53 e Å3
236 parametersΔρmin = 0.71 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.3131 (6)0.3030 (4)0.3690 (2)0.0428 (10)
O10.2068 (4)0.2861 (3)0.40670 (16)0.0587 (9)
N10.4011 (4)0.4010 (3)0.37099 (17)0.0424 (9)
H10.48020.40570.34530.051*
C110.3569 (5)0.2212 (4)0.3164 (2)0.0408 (10)
C120.3616 (5)0.1046 (4)0.3269 (2)0.0465 (11)
I120.33344 (6)0.03002 (4)0.41855 (2)0.0856 (2)
C130.3960 (7)0.0328 (4)0.2758 (3)0.0624 (15)
H130.40120.04470.28330.075*
C140.4224 (7)0.0743 (6)0.2143 (3)0.0708 (16)
H140.44540.02460.18040.085*
C150.4156 (7)0.1878 (5)0.2019 (3)0.0661 (15)
H150.43280.21560.15980.079*
C160.3825 (6)0.2609 (4)0.2531 (2)0.0528 (12)
H160.37740.33820.24490.063*
S210.22237 (15)0.49676 (10)0.46480 (6)0.0452 (3)
C220.3745 (5)0.4928 (4)0.4103 (2)0.0391 (10)
C230.4582 (5)0.5937 (4)0.4090 (2)0.0404 (10)
C240.3951 (6)0.6743 (4)0.4536 (2)0.0459 (11)
H240.43630.74730.45890.055*
C250.2706 (6)0.6351 (4)0.4872 (2)0.0450 (11)
C260.1747 (7)0.6894 (5)0.5393 (3)0.0670 (15)
H26A0.05920.68530.52460.080*
H26B0.19130.64570.58000.080*
C270.2152 (10)0.8057 (6)0.5544 (4)0.102 (2)
H27A0.32710.81050.57240.153*
H27B0.14430.83400.58640.153*
H27C0.20120.85000.51440.153*
C370.5889 (6)0.6110 (4)0.3649 (2)0.0508 (12)
O370.6360 (5)0.5341 (3)0.3298 (2)0.0812 (13)
C310.6698 (6)0.7239 (4)0.3620 (2)0.0430 (11)
C320.6757 (6)0.7829 (4)0.3023 (2)0.0503 (12)
Cl320.5699 (2)0.73426 (18)0.23000 (7)0.0917 (5)
C330.7588 (7)0.8843 (5)0.2998 (3)0.0625 (15)
H330.75860.92390.25990.075*
C340.8403 (7)0.9258 (5)0.3554 (3)0.0694 (16)
H340.89950.99260.35330.083*
C350.8363 (7)0.8707 (5)0.4145 (3)0.0671 (15)
H350.89130.90070.45260.081*
C360.7518 (6)0.7711 (4)0.4182 (2)0.0533 (12)
H360.74950.73450.45900.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.047 (3)0.042 (2)0.041 (2)0.002 (2)0.009 (2)0.0023 (19)
O10.067 (2)0.0520 (19)0.063 (2)0.0132 (17)0.0372 (18)0.0111 (16)
N10.044 (2)0.037 (2)0.049 (2)0.0066 (16)0.0220 (17)0.0067 (16)
C110.033 (2)0.047 (2)0.043 (2)0.0056 (19)0.0060 (19)0.005 (2)
C120.038 (3)0.050 (3)0.051 (3)0.008 (2)0.003 (2)0.006 (2)
I120.1151 (4)0.0636 (3)0.0805 (3)0.0053 (2)0.0237 (3)0.0179 (2)
C130.056 (3)0.050 (3)0.081 (4)0.005 (2)0.005 (3)0.024 (3)
C140.063 (4)0.087 (4)0.062 (4)0.006 (3)0.008 (3)0.038 (3)
C150.062 (3)0.091 (5)0.046 (3)0.005 (3)0.013 (3)0.015 (3)
C160.052 (3)0.057 (3)0.051 (3)0.002 (2)0.012 (2)0.006 (2)
S210.0481 (7)0.0445 (6)0.0458 (6)0.0059 (5)0.0213 (5)0.0026 (5)
C220.043 (3)0.042 (2)0.034 (2)0.0005 (19)0.0133 (19)0.0005 (18)
C230.042 (3)0.039 (2)0.041 (2)0.0024 (19)0.016 (2)0.0030 (19)
C240.052 (3)0.037 (2)0.050 (3)0.005 (2)0.019 (2)0.008 (2)
C250.049 (3)0.045 (3)0.044 (2)0.002 (2)0.017 (2)0.006 (2)
C260.072 (4)0.060 (3)0.075 (4)0.006 (3)0.043 (3)0.018 (3)
C270.132 (6)0.076 (4)0.106 (5)0.014 (4)0.072 (5)0.032 (4)
C370.056 (3)0.046 (3)0.054 (3)0.008 (2)0.027 (2)0.010 (2)
O370.094 (3)0.056 (2)0.103 (3)0.024 (2)0.071 (3)0.032 (2)
C310.045 (3)0.042 (2)0.044 (3)0.004 (2)0.022 (2)0.003 (2)
C320.045 (3)0.063 (3)0.046 (3)0.006 (2)0.017 (2)0.000 (2)
Cl320.0881 (12)0.1342 (15)0.0521 (8)0.0034 (11)0.0011 (8)0.0147 (9)
C330.070 (4)0.057 (3)0.065 (3)0.009 (3)0.036 (3)0.020 (3)
C340.077 (4)0.043 (3)0.093 (5)0.014 (3)0.039 (3)0.005 (3)
C350.074 (4)0.063 (3)0.067 (4)0.016 (3)0.020 (3)0.019 (3)
C360.065 (3)0.057 (3)0.040 (3)0.009 (3)0.020 (2)0.001 (2)
Geometric parameters (Å, º) top
C1—O11.214 (5)C24—H240.9300
C1—N11.364 (5)C25—C261.501 (6)
C1—C111.498 (6)C26—C271.441 (8)
N1—C221.370 (5)C26—H26A0.9700
N1—H10.8600C26—H26B0.9700
C11—C161.390 (6)C27—H27A0.9600
C11—C121.395 (6)C27—H27B0.9600
C12—C131.380 (7)C27—H27C0.9600
C12—I122.073 (5)C37—O371.232 (5)
C13—C141.363 (8)C37—C311.493 (6)
C13—H130.9300C31—C361.387 (6)
C14—C151.366 (9)C31—C321.393 (6)
C14—H140.9300C32—C331.381 (7)
C15—C161.389 (7)C32—Cl321.735 (5)
C15—H150.9300C33—C341.351 (8)
C16—H160.9300C33—H330.9300
S21—C221.722 (4)C34—C351.359 (8)
S21—C251.734 (5)C34—H340.9300
C22—C231.377 (6)C35—C361.371 (7)
C23—C241.433 (6)C35—H350.9300
C23—C371.455 (6)C36—H360.9300
C24—C251.348 (6)
O1—C1—N1121.5 (4)C24—C25—S21111.1 (3)
O1—C1—C11123.9 (4)C26—C25—S21117.7 (3)
N1—C1—C11114.6 (4)C27—C26—C25115.6 (5)
C1—N1—C22125.8 (4)C27—C26—H26A108.4
C1—N1—H1117.1C25—C26—H26A108.4
C22—N1—H1117.1C27—C26—H26B108.4
C16—C11—C12118.0 (4)C25—C26—H26B108.4
C16—C11—C1119.4 (4)H26A—C26—H26B107.4
C12—C11—C1122.5 (4)C26—C27—H27A109.5
C13—C12—C11120.0 (5)C26—C27—H27B109.5
C13—C12—I12116.5 (4)H27A—C27—H27B109.5
C11—C12—I12123.5 (3)C26—C27—H27C109.5
C14—C13—C12120.8 (5)H27A—C27—H27C109.5
C14—C13—H13119.6H27B—C27—H27C109.5
C12—C13—H13119.6O37—C37—C23121.5 (4)
C13—C14—C15120.8 (5)O37—C37—C31118.6 (4)
C13—C14—H14119.6C23—C37—C31119.9 (4)
C15—C14—H14119.6C36—C31—C32117.1 (4)
C14—C15—C16118.9 (5)C36—C31—C37121.0 (4)
C14—C15—H15120.5C32—C31—C37121.8 (4)
C16—C15—H15120.5C33—C32—C31121.0 (5)
C15—C16—C11121.5 (5)C33—C32—Cl32118.2 (4)
C15—C16—H16119.3C31—C32—Cl32120.6 (4)
C11—C16—H16119.3C34—C33—C32119.9 (5)
C22—S21—C2591.7 (2)C34—C33—H33120.0
N1—C22—C23125.1 (4)C32—C33—H33120.0
N1—C22—S21122.9 (3)C33—C34—C35120.5 (5)
C23—C22—S21111.9 (3)C33—C34—H34119.7
C22—C23—C24111.2 (4)C35—C34—H34119.7
C22—C23—C37121.5 (4)C34—C35—C36120.4 (5)
C24—C23—C37127.3 (4)C34—C35—H35119.8
C25—C24—C23114.1 (4)C36—C35—H35119.8
C25—C24—H24122.9C35—C36—C31121.1 (5)
C23—C24—H24122.9C35—C36—H36119.5
C24—C25—C26131.2 (4)C31—C36—H36119.5
O1—C1—N1—C225.1 (7)C37—C23—C24—C25178.5 (5)
C11—C1—N1—C22173.9 (4)C23—C24—C25—C26178.0 (5)
O1—C1—C11—C16136.1 (5)C23—C24—C25—S210.8 (5)
N1—C1—C11—C1642.8 (6)C22—S21—C25—C240.7 (4)
O1—C1—C11—C1239.1 (7)C22—S21—C25—C26178.3 (4)
N1—C1—C11—C12142.0 (4)C24—C25—C26—C273.5 (10)
C16—C11—C12—C132.0 (7)S21—C25—C26—C27177.8 (5)
C1—C11—C12—C13177.2 (4)C22—C23—C37—O374.2 (8)
C16—C11—C12—I12178.0 (3)C24—C23—C37—O37178.0 (5)
C1—C11—C12—I126.7 (6)C22—C23—C37—C31176.3 (4)
C11—C12—C13—C141.3 (8)C24—C23—C37—C311.5 (8)
I12—C12—C13—C14177.7 (4)O37—C37—C31—C36119.0 (6)
C12—C13—C14—C150.0 (9)C23—C37—C31—C3660.6 (7)
C13—C14—C15—C160.5 (9)O37—C37—C31—C3256.7 (7)
C14—C15—C16—C110.2 (8)C23—C37—C31—C32123.7 (5)
C12—C11—C16—C151.4 (7)C36—C31—C32—C330.5 (7)
C1—C11—C16—C15176.9 (4)C37—C31—C32—C33176.4 (4)
C1—N1—C22—C23176.0 (4)C36—C31—C32—Cl32177.2 (4)
C1—N1—C22—S210.5 (6)C37—C31—C32—Cl326.9 (6)
C25—S21—C22—N1177.4 (4)C31—C32—C33—C342.1 (8)
C25—S21—C22—C230.4 (4)Cl32—C32—C33—C34178.9 (4)
N1—C22—C23—C24176.9 (4)C32—C33—C34—C352.4 (8)
S21—C22—C23—C240.0 (5)C33—C34—C35—C361.1 (9)
N1—C22—C23—C371.2 (7)C34—C35—C36—C310.5 (8)
S21—C22—C23—C37178.1 (4)C32—C31—C36—C350.8 (7)
C22—C23—C24—C250.6 (6)C37—C31—C36—C35175.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O370.862.022.665 (5)131
C33—H33···O37i0.932.443.322 (7)159
C15—H15···Cg2ii0.932.923.453 (6)118
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2.
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-2-methoxybenzamide (V) top
Crystal data top
C21H18ClNO3SZ = 2
Mr = 399.87F(000) = 416
Triclinic, P1Dx = 1.403 Mg m3
a = 7.4798 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4237 (5) ÅCell parameters from 5014 reflections
c = 12.0933 (5) Åθ = 1.8–29.2°
α = 105.814 (2)°µ = 0.33 mm1
β = 101.959 (3)°T = 294 K
γ = 99.187 (3)°Block, colourless
V = 946.66 (7) Å30.25 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2406 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.047
φ and ω scansθmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 99
Tmin = 0.908, Tmax = 0.951k = 1414
20919 measured reflectionsl = 1515
3959 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2991P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3959 reflectionsΔρmax = 0.27 e Å3
246 parametersΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.0867 (3)0.3228 (2)0.2731 (2)0.0441 (6)
O10.1139 (3)0.41653 (16)0.24242 (15)0.0582 (5)
N10.1477 (3)0.33071 (18)0.38926 (17)0.0457 (5)
H10.13720.26180.40600.055*
C110.0209 (3)0.1991 (2)0.1865 (2)0.0449 (6)
C120.0288 (3)0.0833 (2)0.2063 (2)0.0481 (6)
C130.1416 (4)0.0247 (3)0.1210 (2)0.0627 (8)
H130.14580.10130.13450.075*
C140.2470 (4)0.0186 (3)0.0164 (3)0.0708 (8)
H140.32450.09130.04000.085*
C150.2401 (4)0.0934 (3)0.0064 (2)0.0686 (8)
H150.31040.09650.07820.082*
C160.1279 (4)0.2010 (3)0.0786 (2)0.0557 (7)
H160.12360.27680.06350.067*
O120.0804 (3)0.08329 (16)0.31140 (16)0.0631 (5)
C1210.0715 (5)0.0305 (3)0.3394 (3)0.0893 (11)
H12A0.05530.06470.33760.134*
H12B0.15180.01440.41750.134*
H12C0.11210.08910.28200.134*
S210.27094 (9)0.58442 (6)0.46466 (6)0.0500 (2)
C220.2251 (3)0.4400 (2)0.4826 (2)0.0414 (6)
C230.2691 (3)0.4464 (2)0.6010 (2)0.0460 (6)
C240.3393 (3)0.5733 (2)0.6764 (2)0.0502 (6)
H240.37430.59570.75910.060*
C250.3506 (3)0.6574 (2)0.6180 (2)0.0484 (6)
C260.4251 (4)0.7971 (2)0.6691 (3)0.0673 (8)
H26A0.38600.82660.74140.081*
H26B0.56110.81430.69140.081*
C270.3657 (6)0.8705 (3)0.5901 (3)0.1093 (14)
H27A0.41880.85130.52330.164*
H27B0.40860.95810.63360.164*
H27C0.23120.84970.56210.164*
C370.2486 (4)0.3369 (2)0.6398 (2)0.0565 (7)
O370.2028 (4)0.23012 (18)0.56934 (17)0.0930 (8)
C310.2781 (4)0.3534 (2)0.7703 (2)0.0488 (6)
C320.4281 (4)0.3240 (2)0.8355 (2)0.0472 (6)
Cl320.60371 (13)0.27880 (9)0.77183 (8)0.0882 (3)
C330.4446 (4)0.3309 (2)0.9529 (2)0.0529 (7)
H330.54770.31130.99580.064*
C340.3090 (4)0.3666 (2)1.0064 (2)0.0590 (7)
H340.31880.37081.08540.071*
C350.1598 (5)0.3958 (3)0.9431 (3)0.0698 (8)
H350.06710.41940.97920.084*
C360.1436 (4)0.3910 (3)0.8266 (3)0.0655 (8)
H360.04190.41320.78530.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0465 (14)0.0477 (15)0.0463 (14)0.0150 (12)0.0155 (12)0.0234 (12)
O10.0830 (13)0.0478 (11)0.0503 (10)0.0142 (9)0.0193 (9)0.0250 (9)
N10.0554 (12)0.0386 (12)0.0451 (12)0.0061 (10)0.0084 (10)0.0226 (9)
C110.0461 (14)0.0490 (15)0.0428 (14)0.0119 (12)0.0137 (11)0.0175 (11)
C120.0484 (15)0.0478 (16)0.0499 (15)0.0097 (12)0.0125 (12)0.0194 (12)
C130.0682 (19)0.0495 (17)0.0632 (18)0.0043 (14)0.0122 (15)0.0154 (14)
C140.070 (2)0.063 (2)0.0643 (19)0.0005 (15)0.0074 (16)0.0104 (15)
C150.0669 (19)0.079 (2)0.0498 (16)0.0110 (16)0.0009 (14)0.0176 (16)
C160.0595 (17)0.0605 (18)0.0522 (16)0.0161 (14)0.0140 (13)0.0253 (14)
O120.0825 (13)0.0408 (11)0.0614 (11)0.0091 (9)0.0015 (10)0.0248 (9)
C1210.133 (3)0.0502 (19)0.082 (2)0.0174 (19)0.006 (2)0.0364 (17)
S210.0600 (4)0.0435 (4)0.0528 (4)0.0102 (3)0.0181 (3)0.0240 (3)
C220.0394 (13)0.0431 (14)0.0465 (14)0.0106 (11)0.0105 (11)0.0218 (11)
C230.0487 (14)0.0449 (15)0.0465 (14)0.0104 (12)0.0083 (11)0.0213 (12)
C240.0533 (15)0.0507 (16)0.0464 (14)0.0091 (12)0.0095 (12)0.0194 (12)
C250.0488 (15)0.0436 (15)0.0538 (15)0.0085 (12)0.0155 (12)0.0168 (12)
C260.075 (2)0.0486 (17)0.077 (2)0.0071 (15)0.0270 (16)0.0169 (15)
C270.166 (4)0.053 (2)0.102 (3)0.014 (2)0.017 (3)0.033 (2)
C370.0731 (19)0.0435 (16)0.0501 (15)0.0072 (14)0.0057 (14)0.0218 (13)
O370.168 (2)0.0439 (13)0.0499 (11)0.0041 (13)0.0005 (13)0.0204 (10)
C310.0626 (17)0.0388 (14)0.0467 (14)0.0091 (12)0.0097 (13)0.0212 (11)
C320.0539 (15)0.0459 (15)0.0469 (14)0.0119 (12)0.0154 (12)0.0210 (11)
Cl320.0863 (6)0.1248 (8)0.0851 (6)0.0477 (5)0.0455 (5)0.0531 (5)
C330.0552 (16)0.0541 (16)0.0487 (15)0.0070 (13)0.0060 (13)0.0238 (12)
C340.084 (2)0.0474 (16)0.0500 (16)0.0122 (15)0.0233 (16)0.0201 (13)
C350.092 (2)0.0614 (19)0.078 (2)0.0336 (17)0.0466 (19)0.0299 (16)
C360.0693 (19)0.0625 (19)0.076 (2)0.0286 (16)0.0170 (16)0.0339 (16)
Geometric parameters (Å, º) top
C1—O11.226 (3)C23—C371.449 (3)
C1—N11.357 (3)C24—C251.340 (3)
C1—C111.491 (3)C24—H240.9300
N1—C221.378 (3)C25—C261.508 (4)
N1—H10.8600C26—C271.481 (4)
C11—C161.390 (3)C26—H26A0.9700
C11—C121.401 (3)C26—H26B0.9700
C12—O121.361 (3)C27—H27A0.9600
C12—C131.383 (4)C27—H27B0.9600
C13—C141.370 (4)C27—H27C0.9600
C13—H130.9300C37—O371.229 (3)
C14—C151.376 (4)C37—C311.501 (3)
C14—H140.9300C31—C321.376 (3)
C15—C161.377 (4)C31—C361.387 (4)
C15—H150.9300C32—C331.380 (3)
C16—H160.9300C32—Cl321.733 (3)
O12—C1211.425 (3)C33—C341.369 (4)
C121—H12A0.9600C33—H330.9300
C121—H12B0.9600C34—C351.359 (4)
C121—H12C0.9600C34—H340.9300
S21—C221.712 (2)C35—C361.373 (4)
S21—C251.741 (3)C35—H350.9300
C22—C231.379 (3)C36—H360.9300
C23—C241.431 (3)
O1—C1—N1120.2 (2)C25—C24—H24122.8
O1—C1—C11121.7 (2)C23—C24—H24122.8
N1—C1—C11118.0 (2)C24—C25—C26128.3 (2)
C1—N1—C22125.3 (2)C24—C25—S21110.88 (19)
C1—N1—H1117.3C26—C25—S21120.8 (2)
C22—N1—H1117.3C27—C26—C25116.0 (3)
C16—C11—C12117.9 (2)C27—C26—H26A108.3
C16—C11—C1116.2 (2)C25—C26—H26A108.3
C12—C11—C1125.9 (2)C27—C26—H26B108.3
O12—C12—C13122.6 (2)C25—C26—H26B108.3
O12—C12—C11116.9 (2)H26A—C26—H26B107.4
C13—C12—C11120.5 (2)C26—C27—H27A109.5
C14—C13—C12119.9 (3)C26—C27—H27B109.5
C14—C13—H13120.1H27A—C27—H27B109.5
C12—C13—H13120.1C26—C27—H27C109.5
C13—C14—C15121.0 (3)H27A—C27—H27C109.5
C13—C14—H14119.5H27B—C27—H27C109.5
C15—C14—H14119.5O37—C37—C23122.3 (2)
C14—C15—C16119.1 (3)O37—C37—C31118.4 (2)
C14—C15—H15120.4C23—C37—C31119.2 (2)
C16—C15—H15120.4C32—C31—C36117.8 (2)
C15—C16—C11121.7 (3)C32—C31—C37122.4 (2)
C15—C16—H16119.2C36—C31—C37119.6 (2)
C11—C16—H16119.2C31—C32—C33121.4 (2)
C12—O12—C121119.6 (2)C31—C32—Cl32120.44 (19)
O12—C121—H12A109.5C33—C32—Cl32118.2 (2)
O12—C121—H12B109.5C34—C33—C32119.8 (2)
H12A—C121—H12B109.5C34—C33—H33120.1
O12—C121—H12C109.5C32—C33—H33120.1
H12A—C121—H12C109.5C35—C34—C33119.5 (3)
H12B—C121—H12C109.5C35—C34—H34120.3
C22—S21—C2591.63 (12)C33—C34—H34120.3
N1—C22—C23124.2 (2)C34—C35—C36121.1 (3)
N1—C22—S21123.58 (17)C34—C35—H35119.5
C23—C22—S21112.23 (18)C36—C35—H35119.5
C22—C23—C24110.8 (2)C35—C36—C31120.4 (3)
C22—C23—C37123.0 (2)C35—C36—H36119.8
C24—C23—C37126.2 (2)C31—C36—H36119.8
C25—C24—C23114.5 (2)
O1—C1—N1—C226.8 (4)C22—C23—C24—C251.0 (3)
C11—C1—N1—C22170.4 (2)C37—C23—C24—C25177.7 (2)
O1—C1—C11—C1615.9 (3)C23—C24—C25—C26177.3 (2)
N1—C1—C11—C16161.3 (2)C23—C24—C25—S210.9 (3)
O1—C1—C11—C12166.8 (2)C22—S21—C25—C240.4 (2)
N1—C1—C11—C1216.1 (4)C22—S21—C25—C26177.9 (2)
C16—C11—C12—O12178.5 (2)C24—C25—C26—C27160.9 (3)
C1—C11—C12—O124.2 (4)S21—C25—C26—C2721.1 (4)
C16—C11—C12—C130.6 (4)C22—C23—C37—O375.2 (4)
C1—C11—C12—C13176.7 (2)C24—C23—C37—O37173.4 (3)
O12—C12—C13—C14179.4 (3)C22—C23—C37—C31172.8 (2)
C11—C12—C13—C140.3 (4)C24—C23—C37—C318.6 (4)
C12—C13—C14—C151.3 (5)O37—C37—C31—C3270.3 (4)
C13—C14—C15—C161.3 (5)C23—C37—C31—C32111.7 (3)
C14—C15—C16—C110.3 (4)O37—C37—C31—C36104.9 (3)
C12—C11—C16—C150.6 (4)C23—C37—C31—C3673.2 (3)
C1—C11—C16—C15177.0 (2)C36—C31—C32—C330.3 (4)
C13—C12—O12—C1214.0 (4)C37—C31—C32—C33174.9 (2)
C11—C12—O12—C121176.9 (3)C36—C31—C32—Cl32178.9 (2)
C1—N1—C22—C23173.4 (2)C37—C31—C32—Cl325.9 (3)
C1—N1—C22—S214.5 (3)C31—C32—C33—C340.6 (4)
C25—S21—C22—N1178.0 (2)Cl32—C32—C33—C34179.8 (2)
C25—S21—C22—C230.16 (19)C32—C33—C34—C350.5 (4)
N1—C22—C23—C24177.4 (2)C33—C34—C35—C360.5 (4)
S21—C22—C23—C240.7 (3)C34—C35—C36—C311.4 (4)
N1—C22—C23—C373.8 (4)C32—C31—C36—C351.3 (4)
S21—C22—C23—C37178.1 (2)C37—C31—C36—C35174.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.861.972.651 (3)135
N1—H1···O370.862.082.716 (3)130
C13—H13···Cg2i0.932.903.782 (4)158
C36—H36···O1ii0.932.483.306 (4)147
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+1.
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-2,6-difluorobenzamide (VI) top
Crystal data top
C20H14ClF2NO2SF(000) = 3328
Mr = 405.83Dx = 1.478 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
a = 58.0164 (10) ÅCell parameters from 6468 reflections
b = 7.8002 (2) Åθ = 3.1–66.7°
c = 16.1365 (3) ŵ = 3.24 mm1
β = 92.105 (1)°T = 294 K
V = 7297.5 (3) Å3Block, green
Z = 160.15 × 0.15 × 0.10 mm
Data collection top
Bruker Kappa APEXII
diffractometer
3979 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.109
φ and ω scansθmax = 66.7°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 6866
Tmin = 0.601, Tmax = 0.753k = 89
42600 measured reflectionsl = 1919
6468 independent reflections
Refinement top
Refinement on F270 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0617P)2 + 13.9466P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6468 reflectionsΔρmax = 0.35 e Å3
572 parametersΔρmin = 0.43 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.62024 (6)0.3614 (5)0.6424 (2)0.0425 (10)
O110.61145 (4)0.3990 (4)0.70712 (17)0.0629 (9)
N110.64277 (5)0.3177 (5)0.63965 (18)0.0474 (9)
H110.64820.29850.59170.057*
C1110.60684 (6)0.3554 (5)0.5617 (2)0.0420 (9)
C1120.58473 (7)0.2861 (6)0.5570 (2)0.0489 (10)
F1120.57624 (4)0.2166 (4)0.62578 (16)0.0782 (9)
C1130.57151 (7)0.2797 (6)0.4849 (3)0.0615 (13)
H1130.55690.23020.48410.074*
C1140.58006 (7)0.3469 (6)0.4143 (3)0.0614 (13)
H1140.57110.34430.36520.074*
C1150.60171 (7)0.4184 (6)0.4149 (3)0.0585 (12)
H1150.60760.46480.36690.070*
C1160.61442 (6)0.4194 (6)0.4880 (3)0.0502 (11)
F1160.63565 (4)0.4904 (4)0.48860 (16)0.0785 (9)
S1210.64917 (2)0.32607 (15)0.80796 (6)0.0471 (3)
C1220.65768 (6)0.3016 (5)0.7079 (2)0.0396 (9)
C1230.68075 (6)0.2583 (5)0.7043 (2)0.0407 (9)
C1240.69108 (6)0.2443 (5)0.7861 (2)0.0424 (10)
H1240.70650.21590.79610.051*
C1250.67654 (6)0.2759 (6)0.8468 (2)0.0456 (10)
C1260.68120 (7)0.2728 (7)0.9397 (2)0.0628 (13)
H12A0.68290.38960.95960.075*
H12B0.66800.22300.96600.075*
C1270.70239 (8)0.1727 (7)0.9648 (3)0.0711 (14)
H12C0.71570.22840.94380.107*
H12D0.70120.05890.94240.107*
H12E0.70380.16681.02420.107*
C1370.69234 (6)0.2357 (6)0.6271 (2)0.0470 (10)
O1370.68288 (5)0.2540 (5)0.55904 (16)0.0701 (10)
C1310.71751 (7)0.1829 (6)0.6344 (2)0.0480 (11)
C1320.73497 (8)0.2898 (6)0.6141 (3)0.0636 (13)
Cl120.72898 (3)0.5018 (2)0.58879 (12)0.1114 (6)
C1330.75778 (7)0.2361 (8)0.6161 (3)0.0778 (16)
H1330.76950.31190.60300.093*
C1340.76281 (8)0.0730 (7)0.6371 (3)0.0754 (15)
H1340.77790.03420.63550.090*
C1350.74558 (9)0.0378 (7)0.6612 (3)0.0765 (15)
H1350.74940.14850.67820.092*
C1360.72347 (7)0.0126 (7)0.6604 (3)0.0575 (12)
H1360.71210.06270.67670.069*
C210.63105 (7)0.8579 (9)0.6285 (3)0.0422 (10)0.916 (3)
O210.63979 (5)0.9189 (5)0.5677 (3)0.0560 (12)0.916 (3)
N210.60841 (8)0.8128 (11)0.6287 (3)0.0473 (15)0.916 (3)
H210.60300.77710.67450.057*0.916 (3)
C2110.64465 (7)0.8237 (11)0.7074 (3)0.0404 (11)0.916 (3)
C2120.66623 (10)0.7482 (11)0.7052 (3)0.0452 (15)0.916 (3)
F2120.67381 (7)0.6941 (5)0.6325 (2)0.0700 (15)0.916 (3)
C2130.67994 (12)0.7200 (14)0.7750 (3)0.052 (2)0.916 (3)
H2130.69430.66840.77120.062*0.916 (3)
C2140.67207 (14)0.7691 (19)0.8504 (3)0.058 (2)0.916 (3)
H2140.68110.74900.89820.069*0.916 (3)
C2150.65095 (11)0.848 (2)0.8566 (3)0.0600 (15)0.916 (3)
H2150.64570.88430.90750.072*0.916 (3)
C2160.63786 (8)0.8702 (12)0.7846 (3)0.0513 (13)0.916 (3)
F2160.61691 (5)0.9467 (8)0.7899 (3)0.0806 (16)0.916 (3)
S2210.60210 (3)0.8752 (3)0.46262 (13)0.0489 (4)0.916 (3)
C2220.59333 (8)0.8206 (13)0.5594 (3)0.0420 (11)0.916 (3)
C2230.57043 (7)0.7760 (14)0.5602 (3)0.0444 (11)0.916 (3)
C2240.56012 (7)0.7857 (9)0.4785 (2)0.0471 (14)0.916 (3)
H2240.54470.75890.46670.056*0.916 (3)
C2250.57460 (7)0.8368 (7)0.4200 (2)0.0500 (13)0.916 (3)
C2260.57012 (8)0.8649 (9)0.3285 (3)0.0736 (18)0.916 (3)
H22A0.57520.97960.31450.088*0.916 (3)
H22B0.57940.78450.29830.088*0.916 (3)
C2270.54616 (10)0.8451 (12)0.3008 (3)0.111 (3)0.916 (3)
H22C0.53660.91500.33440.166*0.916 (3)
H22D0.54170.72720.30590.166*0.916 (3)
H22E0.54440.88010.24390.166*0.916 (3)
C2370.55882 (7)0.7266 (7)0.6341 (3)0.0490 (11)0.916 (3)
O2370.56891 (13)0.712 (3)0.7020 (3)0.0730 (11)0.916 (3)
C2310.53372 (8)0.6783 (6)0.6271 (3)0.0488 (12)0.916 (3)
C2320.51612 (7)0.7917 (6)0.6099 (3)0.0512 (13)0.916 (3)
Cl220.52193 (2)1.0065 (2)0.59302 (11)0.0765 (5)0.916 (3)
C2330.49327 (8)0.7397 (8)0.6065 (4)0.0714 (18)0.916 (3)
H2330.48160.81920.59600.086*0.916 (3)
C2340.48803 (10)0.5731 (9)0.6185 (6)0.097 (3)0.916 (3)
H2340.47270.53730.61490.116*0.916 (3)
C2350.50504 (11)0.4573 (9)0.6360 (15)0.112 (3)0.916 (3)
H2350.50130.34320.64560.134*0.916 (3)
C2360.52772 (10)0.5089 (8)0.6395 (10)0.085 (2)0.916 (3)
H2360.53930.42830.65040.102*0.916 (3)
C310.6279 (5)0.862 (9)0.629 (2)0.0422 (10)0.084 (3)
O310.6340 (7)0.957 (7)0.574 (3)0.0560 (12)0.084 (3)
N310.6070 (6)0.784 (13)0.627 (3)0.0473 (15)0.084 (3)
H310.60380.71720.66700.057*0.084 (3)
C3110.6419 (5)0.841 (11)0.7086 (19)0.0404 (11)0.084 (3)
C3120.6643 (8)0.779 (14)0.707 (2)0.0452 (15)0.084 (3)
F3120.6739 (9)0.757 (9)0.634 (3)0.0700 (15)0.084 (3)
C3130.6779 (11)0.76 (2)0.778 (3)0.052 (2)0.084 (3)
H3130.69290.71680.77470.062*0.084 (3)
C3140.6691 (13)0.80 (2)0.853 (2)0.058 (2)0.084 (3)
H3140.67850.79100.90080.069*0.084 (3)
C3150.6465 (13)0.85 (3)0.859 (2)0.0600 (15)0.084 (3)
H3150.64020.87090.90980.072*0.084 (3)
C3160.6338 (7)0.872 (15)0.786 (2)0.0600 (15)0.084 (3)
F3160.6110 (6)0.910 (11)0.791 (3)0.0806 (16)0.084 (3)
S3210.5965 (4)0.889 (4)0.4680 (16)0.0489 (4)0.084 (3)
C3220.5904 (5)0.804 (15)0.563 (3)0.0420 (11)0.084 (3)
C3230.5673 (5)0.772 (15)0.570 (3)0.0444 (11)0.084 (3)
C3240.5550 (4)0.802 (11)0.493 (2)0.0471 (14)0.084 (3)
H3240.53920.78230.48590.056*0.084 (3)
C3250.5681 (5)0.862 (7)0.4326 (15)0.0500 (13)0.084 (3)
C3260.5625 (7)0.878 (7)0.3409 (17)0.0736 (18)0.084 (3)
H32A0.54900.94990.33280.088*0.084 (3)
H32B0.57530.93400.31480.088*0.084 (3)
C3270.5581 (13)0.715 (9)0.300 (3)0.111 (3)0.084 (3)
H32C0.55240.73500.24380.166*0.084 (3)
H32D0.54690.65100.32910.166*0.084 (3)
H32E0.57220.65030.29830.166*0.084 (3)
C3370.5576 (4)0.704 (4)0.645 (2)0.0490 (11)0.084 (3)
O3370.5681 (14)0.70 (3)0.712 (3)0.0730 (11)0.084 (3)
C3310.5326 (5)0.652 (2)0.642 (3)0.0488 (12)0.084 (3)
C3320.5145 (4)0.766 (2)0.643 (3)0.0512 (13)0.084 (3)
Cl320.5198 (3)0.9818 (19)0.6615 (13)0.0765 (5)0.084 (3)
C3330.4919 (4)0.710 (3)0.644 (4)0.0714 (18)0.084 (3)
H3330.47990.78910.64750.086*0.084 (3)
C3340.4872 (6)0.541 (4)0.641 (9)0.097 (3)0.084 (3)
H3340.47200.50330.63760.116*0.084 (3)
C3350.5047 (8)0.425 (3)0.643 (18)0.112 (3)0.084 (3)
H3350.50140.30780.64090.134*0.084 (3)
C3360.5272 (7)0.480 (3)0.648 (13)0.085 (2)0.084 (3)
H3360.53900.40040.65610.102*0.084 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.031 (2)0.052 (3)0.044 (2)0.0019 (18)0.0009 (17)0.0024 (19)
O110.0433 (16)0.094 (3)0.0514 (17)0.0078 (16)0.0052 (13)0.0090 (17)
N110.0327 (17)0.073 (3)0.0367 (16)0.0038 (16)0.0006 (13)0.0050 (16)
C1110.033 (2)0.046 (3)0.046 (2)0.0029 (17)0.0002 (17)0.0033 (19)
C1120.040 (2)0.060 (3)0.047 (2)0.000 (2)0.0017 (18)0.003 (2)
F1120.0516 (15)0.115 (2)0.0684 (17)0.0265 (15)0.0043 (13)0.0145 (16)
C1130.037 (2)0.080 (4)0.067 (3)0.004 (2)0.007 (2)0.006 (3)
C1140.053 (3)0.079 (4)0.051 (3)0.015 (2)0.017 (2)0.004 (2)
C1150.046 (3)0.081 (4)0.048 (2)0.005 (2)0.002 (2)0.005 (2)
C1160.034 (2)0.060 (3)0.057 (3)0.0057 (19)0.0027 (19)0.003 (2)
F1160.0486 (14)0.119 (3)0.0671 (16)0.0282 (15)0.0029 (12)0.0277 (16)
S1210.0398 (5)0.0651 (8)0.0367 (5)0.0007 (5)0.0064 (4)0.0035 (5)
C1220.036 (2)0.049 (3)0.0334 (18)0.0019 (18)0.0012 (15)0.0015 (17)
C1230.035 (2)0.053 (3)0.0338 (18)0.0017 (17)0.0026 (15)0.0039 (18)
C1240.036 (2)0.053 (3)0.0379 (19)0.0023 (18)0.0025 (16)0.0036 (18)
C1250.043 (2)0.061 (3)0.0321 (18)0.0013 (19)0.0022 (16)0.0027 (19)
C1260.060 (3)0.096 (4)0.033 (2)0.007 (3)0.0049 (19)0.002 (2)
C1270.091 (4)0.078 (4)0.043 (2)0.008 (3)0.013 (2)0.002 (2)
C1370.037 (2)0.070 (3)0.0337 (19)0.0052 (19)0.0007 (16)0.006 (2)
O1370.0469 (17)0.131 (3)0.0322 (14)0.0169 (18)0.0028 (12)0.0050 (17)
C1310.040 (2)0.071 (3)0.0329 (19)0.000 (2)0.0050 (17)0.015 (2)
C1320.053 (3)0.065 (4)0.072 (3)0.006 (2)0.001 (2)0.006 (3)
Cl120.0925 (11)0.0792 (12)0.1628 (17)0.0073 (9)0.0097 (10)0.0280 (11)
C1330.034 (3)0.087 (5)0.113 (4)0.003 (2)0.004 (3)0.010 (3)
C1340.047 (3)0.076 (4)0.102 (4)0.011 (3)0.009 (3)0.024 (3)
C1350.075 (4)0.066 (4)0.088 (4)0.009 (3)0.019 (3)0.008 (3)
C1360.038 (2)0.073 (4)0.061 (3)0.001 (2)0.003 (2)0.018 (2)
C210.038 (2)0.042 (3)0.046 (2)0.003 (2)0.0000 (18)0.0006 (19)
O210.040 (2)0.077 (3)0.0511 (18)0.0001 (18)0.0032 (17)0.0132 (19)
N210.0347 (19)0.065 (4)0.0423 (18)0.0035 (17)0.0001 (14)0.009 (2)
C2110.033 (2)0.044 (3)0.044 (2)0.003 (2)0.0016 (17)0.0009 (18)
C2120.037 (2)0.053 (5)0.045 (2)0.000 (2)0.0047 (18)0.002 (2)
F2120.0557 (15)0.100 (4)0.0553 (15)0.027 (2)0.0127 (12)0.001 (2)
C2130.039 (3)0.057 (7)0.060 (3)0.004 (2)0.004 (2)0.006 (3)
C2140.054 (3)0.063 (7)0.055 (3)0.011 (3)0.017 (2)0.006 (2)
C2150.055 (4)0.081 (4)0.044 (2)0.008 (5)0.001 (2)0.013 (2)
C2160.037 (3)0.061 (3)0.056 (3)0.003 (3)0.003 (2)0.009 (2)
F2160.050 (2)0.126 (4)0.0659 (17)0.023 (3)0.0009 (17)0.034 (2)
S2210.0362 (10)0.0709 (10)0.0400 (6)0.0003 (9)0.0058 (7)0.0067 (6)
C2220.039 (2)0.052 (4)0.0343 (19)0.002 (2)0.0004 (18)0.0022 (18)
C2230.038 (2)0.060 (3)0.036 (2)0.001 (2)0.0042 (18)0.005 (2)
C2240.036 (2)0.072 (4)0.033 (2)0.006 (3)0.0013 (18)0.001 (2)
C2250.045 (3)0.070 (4)0.036 (2)0.000 (2)0.0013 (19)0.000 (2)
C2260.057 (3)0.126 (5)0.038 (2)0.016 (3)0.003 (2)0.010 (3)
C2270.082 (5)0.204 (9)0.044 (3)0.018 (5)0.016 (3)0.019 (4)
C2370.039 (2)0.068 (3)0.039 (2)0.002 (2)0.0002 (18)0.009 (2)
O2370.0525 (19)0.127 (4)0.039 (2)0.0064 (19)0.0044 (18)0.022 (3)
C2310.041 (2)0.061 (3)0.044 (3)0.001 (2)0.0021 (18)0.013 (2)
C2320.045 (3)0.056 (3)0.053 (3)0.008 (2)0.001 (2)0.002 (2)
Cl220.0661 (8)0.0607 (9)0.1017 (13)0.0047 (7)0.0091 (8)0.0010 (8)
C2330.044 (3)0.071 (4)0.098 (5)0.003 (3)0.009 (3)0.012 (3)
C2340.041 (3)0.083 (5)0.166 (9)0.007 (3)0.007 (4)0.034 (5)
C2350.066 (4)0.065 (5)0.206 (9)0.015 (3)0.033 (4)0.041 (7)
C2360.057 (3)0.071 (4)0.129 (7)0.012 (3)0.029 (3)0.043 (5)
C310.038 (2)0.042 (3)0.046 (2)0.003 (2)0.0000 (18)0.0006 (19)
O310.040 (2)0.077 (3)0.0511 (18)0.0001 (18)0.0032 (17)0.0132 (19)
N310.0347 (19)0.065 (4)0.0423 (18)0.0035 (17)0.0001 (14)0.009 (2)
C3110.033 (2)0.044 (3)0.044 (2)0.003 (2)0.0016 (17)0.0009 (18)
C3120.037 (2)0.053 (5)0.045 (2)0.000 (2)0.0047 (18)0.002 (2)
F3120.0557 (15)0.100 (4)0.0553 (15)0.027 (2)0.0127 (12)0.001 (2)
C3130.039 (3)0.057 (7)0.060 (3)0.004 (2)0.004 (2)0.006 (3)
C3140.054 (3)0.063 (7)0.055 (3)0.011 (3)0.017 (2)0.006 (2)
C3150.055 (4)0.081 (4)0.044 (2)0.008 (5)0.001 (2)0.013 (2)
C3160.055 (4)0.081 (4)0.044 (2)0.008 (5)0.001 (2)0.013 (2)
F3160.050 (2)0.126 (4)0.0659 (17)0.023 (3)0.0009 (17)0.034 (2)
S3210.0362 (10)0.0709 (10)0.0400 (6)0.0003 (9)0.0058 (7)0.0067 (6)
C3220.039 (2)0.052 (4)0.0343 (19)0.002 (2)0.0004 (18)0.0022 (18)
C3230.038 (2)0.060 (3)0.036 (2)0.001 (2)0.0042 (18)0.005 (2)
C3240.036 (2)0.072 (4)0.033 (2)0.006 (3)0.0013 (18)0.001 (2)
C3250.045 (3)0.070 (4)0.036 (2)0.000 (2)0.0013 (19)0.000 (2)
C3260.057 (3)0.126 (5)0.038 (2)0.016 (3)0.003 (2)0.010 (3)
C3270.082 (5)0.204 (9)0.044 (3)0.018 (5)0.016 (3)0.019 (4)
C3370.039 (2)0.068 (3)0.039 (2)0.002 (2)0.0002 (18)0.009 (2)
O3370.0525 (19)0.127 (4)0.039 (2)0.0064 (19)0.0044 (18)0.022 (3)
C3310.041 (2)0.061 (3)0.044 (3)0.001 (2)0.0021 (18)0.013 (2)
C3320.045 (3)0.056 (3)0.053 (3)0.008 (2)0.001 (2)0.002 (2)
Cl320.0661 (8)0.0607 (9)0.1017 (13)0.0047 (7)0.0091 (8)0.0010 (8)
C3330.044 (3)0.071 (4)0.098 (5)0.003 (3)0.009 (3)0.012 (3)
C3340.041 (3)0.083 (5)0.166 (9)0.007 (3)0.007 (4)0.034 (5)
C3350.066 (4)0.065 (5)0.206 (9)0.015 (3)0.033 (4)0.041 (7)
C3360.057 (3)0.071 (4)0.129 (7)0.012 (3)0.029 (3)0.043 (5)
Geometric parameters (Å, º) top
C11—O111.215 (4)C224—H2240.9300
C11—N111.354 (4)C225—C2261.507 (6)
C11—C1111.493 (5)C226—C2271.452 (7)
N11—C1221.381 (4)C226—H22A0.9700
N11—H110.8600C226—H22B0.9700
C111—C1161.376 (5)C227—H22C0.9600
C111—C1121.391 (5)C227—H22D0.9600
C112—F1121.345 (5)C227—H22E0.9600
C112—C1131.371 (6)C237—O2371.228 (5)
C113—C1141.364 (6)C237—C2311.505 (5)
C113—H1130.9300C231—C2321.372 (6)
C114—C1151.374 (6)C231—C2361.383 (7)
C114—H1140.9300C232—C2331.386 (6)
C115—C1161.369 (6)C232—Cl221.732 (5)
C115—H1150.9300C233—C2341.350 (8)
C116—F1161.350 (4)C233—H2330.9300
S121—C1221.716 (3)C234—C2351.359 (8)
S121—C1251.730 (4)C234—H2340.9300
C122—C1231.384 (5)C235—C2361.375 (7)
C123—C1241.433 (5)C235—H2350.9300
C123—C1371.448 (5)C236—H2360.9300
C124—C1251.339 (5)C31—O311.218 (7)
C124—H1240.9300C31—N311.360 (7)
C125—C1261.513 (5)C31—C3111.498 (7)
C126—C1271.499 (6)N31—C3221.395 (6)
C126—H12A0.9700N31—H310.8600
C126—H12B0.9700C311—C3161.369 (7)
C127—H12C0.9600C311—C3121.385 (7)
C127—H12D0.9600C312—F3121.337 (7)
C127—H12E0.9600C312—C3131.374 (7)
C137—O1371.218 (4)C313—C3141.370 (8)
C137—C1311.518 (5)C313—H3130.9300
C131—C1321.361 (6)C314—C3151.377 (8)
C131—C1361.432 (6)C314—H3140.9300
C132—C1331.387 (6)C315—C3161.376 (7)
C132—Cl121.736 (5)C315—H3150.9300
C133—C1341.346 (7)C316—F3161.360 (7)
C133—H1330.9300S321—C3221.714 (6)
C134—C1351.388 (7)S321—C3251.740 (6)
C134—H1340.9300C322—C3231.374 (7)
C135—C1361.341 (6)C323—C3241.431 (7)
C135—H1350.9300C323—C3371.443 (7)
C136—H1360.9300C324—C3251.346 (7)
C21—O211.217 (5)C324—H3240.9300
C21—N211.360 (5)C325—C3261.509 (7)
C21—C2111.497 (5)C326—C3271.453 (8)
N21—C2221.395 (5)C326—H32A0.9700
N21—H210.8600C326—H32B0.9700
C211—C2161.369 (5)C327—H32C0.9700
C211—C2121.385 (5)C327—H32D0.9600
C212—F2121.336 (4)C327—H32E0.9600
C212—C2131.373 (5)C337—O3371.229 (7)
C213—C2141.370 (6)C337—C3311.505 (7)
C213—H2130.9300C331—C3321.373 (7)
C214—C2151.378 (7)C331—C3361.383 (8)
C214—H2140.9300C332—C3331.386 (8)
C215—C2161.376 (6)C332—Cl321.733 (7)
C215—H2150.9300C333—C3341.350 (9)
C216—F2161.359 (5)C333—H3330.9300
S221—C2221.714 (4)C334—C3351.360 (9)
S221—C2251.740 (4)C334—H3340.9300
C222—C2231.374 (5)C335—C3361.375 (8)
C223—C2241.430 (5)C335—H3350.9300
C223—C2371.443 (5)C336—H3360.9300
C224—C2251.346 (6)
O11—C11—N11121.7 (3)C224—C225—S221111.2 (3)
O11—C11—C111122.4 (3)C226—C225—S221119.0 (3)
N11—C11—C111115.8 (3)C227—C226—C225114.5 (4)
C11—N11—C122125.0 (3)C227—C226—H22A108.6
C11—N11—H11117.5C225—C226—H22A108.6
C122—N11—H11117.5C227—C226—H22B108.6
C116—C111—C112114.7 (3)C225—C226—H22B108.6
C116—C111—C11124.7 (3)H22A—C226—H22B107.6
C112—C111—C11120.6 (3)C226—C227—H22C109.5
F112—C112—C113118.4 (4)C226—C227—H22D109.5
F112—C112—C111118.5 (3)H22C—C227—H22D109.5
C113—C112—C111123.1 (4)C226—C227—H22E109.5
C114—C113—C112119.0 (4)H22C—C227—H22E109.5
C114—C113—H113120.5H22D—C227—H22E109.5
C112—C113—H113120.5O237—C237—C223122.7 (4)
C113—C114—C115120.7 (4)O237—C237—C231118.2 (4)
C113—C114—H114119.6C223—C237—C231119.0 (3)
C115—C114—H114119.6C232—C231—C236117.1 (4)
C116—C115—C114118.2 (4)C232—C231—C237124.4 (4)
C116—C115—H115120.9C236—C231—C237118.4 (4)
C114—C115—H115120.9C231—C232—C233121.5 (5)
F116—C116—C115118.1 (4)C231—C232—Cl22120.5 (3)
F116—C116—C111117.6 (3)C233—C232—Cl22117.9 (4)
C115—C116—C111124.3 (4)C234—C233—C232119.7 (5)
C122—S121—C12591.36 (17)C234—C233—H233120.1
N11—C122—C123124.5 (3)C232—C233—H233120.1
N11—C122—S121123.2 (3)C233—C234—C235120.2 (5)
C123—C122—S121112.3 (3)C233—C234—H234119.9
C122—C123—C124110.6 (3)C235—C234—H234119.9
C122—C123—C137123.2 (3)C234—C235—C236120.0 (6)
C124—C123—C137126.2 (3)C234—C235—H235120.0
C125—C124—C123114.0 (3)C236—C235—H235120.0
C125—C124—H124123.0C235—C236—C231121.3 (5)
C123—C124—H124123.0C235—C236—H236119.4
C124—C125—C126128.9 (4)C231—C236—H236119.4
C124—C125—S121111.8 (3)O31—C31—N31122.0 (9)
C126—C125—S121119.4 (3)O31—C31—C311122.1 (9)
C127—C126—C125113.0 (3)N31—C31—C311115.5 (8)
C127—C126—H12A109.0C31—N31—C322124.4 (10)
C125—C126—H12A109.0C31—N31—H31117.8
C127—C126—H12B109.0C322—N31—H31117.8
C125—C126—H12B109.0C316—C311—C312115.3 (6)
H12A—C126—H12B107.8C316—C311—C31124.5 (8)
C126—C127—H12C109.5C312—C311—C31120.1 (8)
C126—C127—H12D109.5F312—C312—C313117.9 (10)
H12C—C127—H12D109.5F312—C312—C311118.9 (10)
C126—C127—H12E109.5C313—C312—C311122.9 (7)
H12C—C127—H12E109.5C314—C313—C312118.8 (8)
H12D—C127—H12E109.5C314—C313—H313120.6
O137—C137—C123123.6 (3)C312—C313—H313120.6
O137—C137—C131120.1 (3)C313—C314—C315121.0 (9)
C123—C137—C131116.3 (3)C313—C314—H314119.5
C132—C131—C136117.7 (4)C315—C314—H314119.5
C132—C131—C137122.5 (4)C316—C315—C314117.4 (9)
C136—C131—C137119.7 (4)C316—C315—H315121.3
C131—C132—C133121.8 (5)C314—C315—H315121.3
C131—C132—Cl12119.8 (4)F316—C316—C311117.3 (10)
C133—C132—Cl12118.4 (4)F316—C316—C315117.8 (10)
C134—C133—C132119.3 (5)C311—C316—C315124.4 (7)
C134—C133—H133120.4C322—S321—C32591.1 (4)
C132—C133—H133120.4C323—C322—N31124.1 (8)
C133—C134—C135120.5 (5)C323—C322—S321112.9 (7)
C133—C134—H134119.8N31—C322—S321122.8 (7)
C135—C134—H134119.8C322—C323—C324110.3 (7)
C136—C135—C134120.9 (5)C322—C323—C337123.7 (10)
C136—C135—H135119.6C324—C323—C337125.8 (9)
C134—C135—H135119.6C325—C324—C323114.4 (6)
C135—C136—C131119.7 (4)C325—C324—H324122.8
C135—C136—H136120.2C323—C324—H324122.8
C131—C136—H136120.2C324—C325—C326129.4 (10)
O21—C21—N21122.3 (4)C324—C325—S321111.0 (5)
O21—C21—C211122.2 (4)C326—C325—S321118.6 (8)
N21—C21—C211115.5 (3)C327—C326—C325114.1 (9)
C21—N21—C222124.4 (4)C327—C326—H32A108.7
C21—N21—H21117.8C325—C326—H32A108.7
C222—N21—H21117.8C327—C326—H32B108.7
C216—C211—C212115.3 (4)C325—C326—H32B108.7
C216—C211—C21124.5 (4)H32A—C326—H32B107.6
C212—C211—C21120.1 (3)C326—C327—H32C109.5
F212—C212—C213118.0 (4)C326—C327—H32D109.5
F212—C212—C211119.0 (3)H32C—C327—H32D109.5
C213—C212—C211122.9 (4)C326—C327—H32E109.5
C214—C213—C212118.8 (4)H32C—C327—H32E109.5
C214—C213—H213120.6H32D—C327—H32E109.5
C212—C213—H213120.6O337—C337—C323122.6 (12)
C213—C214—C215121.0 (4)O337—C337—C331118.0 (9)
C213—C214—H214119.5C323—C337—C331118.9 (9)
C215—C214—H214119.5C332—C331—C336117.1 (9)
C216—C215—C214117.4 (4)C332—C331—C337124.2 (9)
C216—C215—H215121.3C336—C331—C337118.4 (8)
C214—C215—H215121.3C331—C332—C333121.3 (8)
F216—C216—C211117.5 (4)C331—C332—Cl32120.0 (8)
F216—C216—C215118.0 (4)C333—C332—Cl32117.6 (8)
C211—C216—C215124.5 (4)C334—C333—C332119.8 (9)
C222—S221—C22591.04 (19)C334—C333—H333120.1
C223—C222—N21124.0 (3)C332—C333—H333120.1
C223—C222—S221113.0 (3)C333—C334—C335120.3 (9)
N21—C222—S221122.8 (3)C333—C334—H334119.9
C222—C223—C224110.5 (3)C335—C334—H334119.9
C222—C223—C237123.8 (4)C334—C335—C336119.8 (10)
C224—C223—C237125.8 (4)C334—C335—H335120.1
C225—C224—C223114.3 (4)C336—C335—H335120.1
C225—C224—H224122.9C335—C336—C331121.1 (11)
C223—C224—H224122.9C335—C336—H336119.5
C224—C225—C226129.8 (4)C331—C336—H336119.5
O11—C11—N11—C1223.8 (7)C222—C223—C224—C2250.7 (10)
C111—C11—N11—C122174.5 (4)C237—C223—C224—C225179.4 (8)
O11—C11—C111—C116136.9 (5)C223—C224—C225—C226178.9 (7)
N11—C11—C111—C11644.8 (6)C223—C224—C225—S2210.3 (8)
O11—C11—C111—C11241.1 (6)C222—S221—C225—C2240.1 (6)
N11—C11—C111—C112137.2 (4)C222—S221—C225—C226179.4 (6)
C116—C111—C112—F112178.2 (4)C224—C225—C226—C2274.8 (10)
C11—C111—C112—F1123.6 (6)S221—C225—C226—C227174.4 (6)
C116—C111—C112—C1130.8 (6)C222—C223—C237—O2373.8 (16)
C11—C111—C112—C113179.0 (4)C224—C223—C237—O237176.1 (14)
F112—C112—C113—C114178.8 (4)C222—C223—C237—C231179.3 (8)
C111—C112—C113—C1141.3 (7)C224—C223—C237—C2310.7 (12)
C112—C113—C114—C1150.7 (7)O237—C237—C231—C232114.4 (12)
C113—C114—C115—C1160.3 (7)C223—C237—C231—C23270.0 (7)
C114—C115—C116—F116179.7 (4)O237—C237—C231—C23665.0 (14)
C114—C115—C116—C1110.9 (7)C223—C237—C231—C236110.6 (10)
C112—C111—C116—F116179.2 (4)C236—C231—C232—C2331.2 (10)
C11—C111—C116—F1161.1 (6)C237—C231—C232—C233178.2 (4)
C112—C111—C116—C1150.4 (7)C236—C231—C232—Cl22179.7 (8)
C11—C111—C116—C115177.7 (4)C237—C231—C232—Cl220.8 (6)
C11—N11—C122—C123179.4 (4)C231—C232—C233—C2341.6 (9)
C11—N11—C122—S1213.0 (6)Cl22—C232—C233—C234179.4 (6)
C125—S121—C122—N11177.2 (4)C232—C233—C234—C2351.7 (16)
C125—S121—C122—C1230.7 (3)C233—C234—C235—C2362 (2)
N11—C122—C123—C124177.3 (4)C234—C235—C236—C2311 (2)
S121—C122—C123—C1240.6 (5)C232—C231—C236—C2351.1 (15)
N11—C122—C123—C1374.1 (7)C237—C231—C236—C235178.4 (10)
S121—C122—C123—C137178.0 (3)O31—C31—N31—C3221 (11)
C122—C123—C124—C1250.2 (5)C311—C31—N31—C322172 (6)
C137—C123—C124—C125178.4 (4)O31—C31—C311—C316122 (9)
C123—C124—C125—C126179.8 (4)N31—C31—C311—C31651 (10)
C123—C124—C125—S1210.3 (5)O31—C31—C311—C31260 (8)
C122—S121—C125—C1240.6 (4)N31—C31—C311—C312127 (8)
C122—S121—C125—C126179.6 (4)C316—C311—C312—F312175 (9)
C124—C125—C126—C12719.6 (7)C31—C311—C312—F3127 (11)
S121—C125—C126—C127160.5 (4)C316—C311—C312—C3132 (13)
C122—C123—C137—O1370.6 (7)C31—C311—C312—C313180 (9)
C124—C123—C137—O137177.7 (4)F312—C312—C313—C314173 (14)
C122—C123—C137—C131178.2 (4)C311—C312—C313—C3140 (17)
C124—C123—C137—C1313.5 (6)C312—C313—C314—C3154 (23)
O137—C137—C131—C13270.4 (6)C313—C314—C315—C3165 (25)
C123—C137—C131—C132110.7 (5)C312—C311—C316—F316171 (9)
O137—C137—C131—C136107.0 (5)C31—C311—C316—F3167 (11)
C123—C137—C131—C13671.8 (5)C312—C311—C316—C3151 (13)
C136—C131—C132—C1331.7 (7)C31—C311—C316—C315179 (10)
C137—C131—C132—C133175.8 (4)C314—C315—C316—F316174 (16)
C136—C131—C132—Cl12175.8 (3)C314—C315—C316—C3112 (20)
C137—C131—C132—Cl126.7 (6)C31—N31—C322—C323159 (11)
C131—C132—C133—C1341.2 (8)C31—N31—C322—S32116 (11)
Cl12—C132—C133—C134178.8 (4)C325—S321—C322—C3236 (8)
C132—C133—C134—C1353.7 (8)C325—S321—C322—N31179 (8)
C133—C134—C135—C1363.1 (8)N31—C322—C323—C324179 (9)
C134—C135—C136—C1310.1 (7)S321—C322—C323—C3246 (11)
C132—C131—C136—C1352.3 (6)N31—C322—C323—C3374 (15)
C137—C131—C136—C135175.3 (4)S321—C322—C323—C337179 (9)
O21—C21—N21—C2224.2 (10)C322—C323—C324—C3253 (12)
C211—C21—N21—C222174.3 (6)C337—C323—C324—C325178 (8)
O21—C21—C211—C216132.4 (8)C323—C324—C325—C326167 (7)
N21—C21—C211—C21649.1 (10)C323—C324—C325—S3211 (9)
O21—C21—C211—C21244.0 (9)C322—S321—C325—C3244 (6)
N21—C21—C211—C212134.6 (7)C322—S321—C325—C326166 (5)
C216—C211—C212—F212177.9 (7)C324—C325—C326—C32763 (7)
C21—C211—C212—F2125.5 (11)S321—C325—C326—C327105 (5)
C216—C211—C212—C2130.6 (12)C322—C323—C337—O33716 (16)
C21—C211—C212—C213177.2 (7)C324—C323—C337—O337169 (16)
F212—C212—C213—C214177.7 (11)C322—C323—C337—C331172 (8)
C211—C212—C213—C2140.3 (14)C324—C323—C337—C3312 (13)
C212—C213—C214—C2150.9 (18)O337—C337—C331—C33297 (13)
C213—C214—C215—C2162 (2)C323—C337—C331—C33275 (6)
C212—C211—C216—F216179.3 (8)O337—C337—C331—C33677 (16)
C21—C211—C216—F2162.7 (11)C323—C337—C331—C336111 (11)
C212—C211—C216—C2150.5 (12)C336—C331—C332—C3334 (10)
C21—C211—C216—C215176.0 (9)C337—C331—C332—C333177 (4)
C214—C215—C216—F216179.5 (13)C336—C331—C332—Cl32164 (10)
C214—C215—C216—C2111.7 (17)C337—C331—C332—Cl3210 (5)
C21—N21—C222—C223179.5 (9)C331—C332—C333—C3343 (11)
C21—N21—C222—S2214.5 (11)Cl32—C332—C333—C334171 (8)
C225—S221—C222—C2230.5 (7)C332—C333—C334—C3355 (20)
C225—S221—C222—N21175.9 (7)C333—C334—C335—C3360 (25)
N21—C222—C223—C224175.6 (8)C334—C335—C336—C3317 (22)
S221—C222—C223—C2240.7 (10)C332—C331—C336—C3359 (15)
N21—C222—C223—C2374.3 (14)C337—C331—C336—C335177 (11)
S221—C222—C223—C237179.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1370.862.132.753 (4)129
N21—H21···O2370.862.102.733 (11)129
N31—H31···O3370.862.222.76 (11)121
N31—H31···O110.862.603.28 (10)137
C114—H114···O337i0.932.503.33 (5)150
C214—H214···O137ii0.932.593.407 (6)146
C314—H314···O137ii0.932.583.42 (4)150
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y+1, z+1/2.
Benzotriazol-1-yl 3,4-dimethoxybenzoate (VII) top
Crystal data top
C15H13N3O4Z = 2
Mr = 299.28F(000) = 312
Triclinic, P1Dx = 1.378 Mg m3
a = 8.1296 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5899 (6) ÅCell parameters from 3424 reflections
c = 10.8824 (8) Åθ = 2.1–27.8°
α = 66.840 (4)°µ = 0.10 mm1
β = 71.533 (4)°T = 294 K
γ = 71.350 (4)°Block, colourless
V = 721.10 (9) Å30.15 × 0.15 × 0.10 mm
Data collection top
Bruker Kappa APEXII
diffractometer
1667 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.051
φ and ω scansθmax = 26.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.921, Tmax = 0.990k = 1212
15518 measured reflectionsl = 1313
2992 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1923P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2992 reflectionsΔρmax = 0.17 e Å3
201 parametersΔρmin = 0.21 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.5541 (3)0.6284 (3)0.6656 (3)0.0519 (6)
O10.6629 (3)0.5557 (2)0.5980 (2)0.0792 (6)
O20.5394 (2)0.57911 (18)0.80862 (17)0.0612 (5)
C110.4229 (3)0.7716 (2)0.6225 (2)0.0435 (5)
C120.4248 (3)0.8391 (2)0.4823 (2)0.0468 (6)
H120.50600.79070.42100.056*
C130.3083 (3)0.9756 (2)0.4352 (2)0.0442 (5)
C140.1853 (3)1.0488 (2)0.5275 (2)0.0465 (6)
C150.1828 (3)0.9810 (3)0.6657 (2)0.0537 (6)
H150.10061.02840.72730.064*
C160.3013 (3)0.8433 (2)0.7129 (2)0.0499 (6)
H160.29910.79870.80620.060*
O130.2994 (2)1.05405 (19)0.30090 (17)0.0628 (5)
C1310.4233 (4)0.9901 (3)0.2010 (3)0.0716 (8)
H13A0.54200.97580.20970.107*
H13B0.40941.05960.11120.107*
H13C0.40260.89150.21440.107*
O140.0788 (2)1.18375 (18)0.47077 (17)0.0663 (5)
C1410.0360 (4)1.2734 (3)0.5554 (3)0.0776 (9)
H14A0.11421.21270.62770.116*
H14B0.10511.36530.50150.116*
H14C0.03371.30260.59400.116*
N210.6660 (3)0.4470 (2)0.8527 (2)0.0562 (6)
N220.6258 (3)0.3075 (2)0.8981 (2)0.0659 (6)
N230.7677 (3)0.2033 (2)0.9335 (2)0.0630 (6)
C23A0.8983 (3)0.2793 (3)0.9080 (2)0.0485 (6)
C241.0717 (3)0.2208 (3)0.9269 (3)0.0599 (7)
H241.11630.11470.96430.072*
C251.1733 (4)0.3254 (3)0.8883 (3)0.0717 (8)
H251.29060.28990.89820.086*
C261.1057 (4)0.4858 (3)0.8339 (3)0.0728 (8)
H261.17980.55330.80960.087*
C270.9358 (4)0.5470 (3)0.8151 (3)0.0624 (7)
H270.89120.65340.77910.075*
C27A0.8342 (3)0.4379 (3)0.8540 (2)0.0481 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0484 (14)0.0488 (13)0.0524 (15)0.0053 (11)0.0135 (11)0.0127 (12)
O10.0779 (13)0.0687 (12)0.0719 (13)0.0249 (10)0.0231 (10)0.0307 (10)
O20.0555 (10)0.0566 (10)0.0559 (11)0.0054 (8)0.0191 (8)0.0112 (8)
C110.0436 (12)0.0374 (11)0.0466 (13)0.0065 (10)0.0107 (10)0.0120 (10)
C120.0424 (12)0.0480 (13)0.0492 (14)0.0045 (10)0.0069 (10)0.0219 (11)
C130.0441 (12)0.0429 (12)0.0451 (13)0.0068 (10)0.0103 (10)0.0157 (10)
C140.0487 (13)0.0382 (12)0.0499 (14)0.0055 (10)0.0126 (11)0.0136 (11)
C150.0533 (14)0.0483 (13)0.0520 (15)0.0029 (11)0.0020 (11)0.0227 (12)
C160.0546 (14)0.0442 (13)0.0442 (13)0.0083 (11)0.0072 (11)0.0128 (11)
O130.0678 (11)0.0606 (10)0.0471 (10)0.0063 (8)0.0163 (8)0.0178 (8)
C1310.0770 (19)0.0800 (19)0.0524 (16)0.0062 (15)0.0084 (14)0.0295 (14)
O140.0695 (11)0.0494 (10)0.0612 (11)0.0145 (9)0.0148 (9)0.0205 (9)
C1410.0727 (18)0.0560 (16)0.081 (2)0.0138 (14)0.0045 (15)0.0311 (15)
N210.0520 (12)0.0455 (11)0.0615 (13)0.0023 (9)0.0222 (10)0.0068 (10)
N220.0638 (14)0.0595 (14)0.0705 (15)0.0192 (11)0.0243 (12)0.0055 (12)
N230.0684 (14)0.0472 (12)0.0688 (15)0.0129 (11)0.0283 (12)0.0040 (11)
C23A0.0509 (14)0.0456 (13)0.0449 (13)0.0093 (11)0.0129 (11)0.0100 (10)
C240.0589 (16)0.0525 (14)0.0605 (16)0.0017 (12)0.0197 (13)0.0137 (12)
C250.0504 (15)0.0762 (19)0.084 (2)0.0084 (14)0.0193 (14)0.0218 (16)
C260.0642 (18)0.0685 (18)0.084 (2)0.0280 (15)0.0185 (15)0.0111 (16)
C270.0713 (18)0.0425 (13)0.0661 (17)0.0146 (13)0.0196 (14)0.0050 (12)
C27A0.0484 (14)0.0444 (13)0.0458 (13)0.0067 (10)0.0113 (10)0.0109 (10)
Geometric parameters (Å, º) top
C1—O11.186 (3)O14—C1411.422 (3)
C1—O21.414 (3)C141—H14A0.9600
C1—C111.455 (3)C141—H14B0.9600
O2—N211.377 (2)C141—H14C0.9600
C11—C161.378 (3)N21—N221.341 (3)
C11—C121.401 (3)N21—C27A1.346 (3)
C12—C131.363 (3)N22—N231.311 (3)
C12—H120.9300N23—C23A1.372 (3)
C13—O131.370 (3)C23A—C27A1.384 (3)
C13—C141.404 (3)C23A—C241.390 (3)
C14—O141.341 (2)C24—C251.358 (4)
C14—C151.380 (3)C24—H240.9300
C15—C161.379 (3)C25—C261.403 (4)
C15—H150.9300C25—H250.9300
C16—H160.9300C26—C271.364 (4)
O13—C1311.417 (3)C26—H260.9300
C131—H13A0.9600C27—C27A1.392 (3)
C131—H13B0.9600C27—H270.9300
C131—H13C0.9600
O1—C1—O2120.6 (2)O14—C141—H14A109.5
O1—C1—C11128.8 (2)O14—C141—H14B109.5
O2—C1—C11110.59 (19)H14A—C141—H14B109.5
N21—O2—C1112.32 (17)O14—C141—H14C109.5
C16—C11—C12119.57 (19)H14A—C141—H14C109.5
C16—C11—C1122.8 (2)H14B—C141—H14C109.5
C12—C11—C1117.59 (19)N22—N21—C27A113.22 (19)
C13—C12—C11120.3 (2)N22—N21—O2119.18 (19)
C13—C12—H12119.8C27A—N21—O2127.6 (2)
C11—C12—H12119.8N23—N22—N21106.6 (2)
C12—C13—O13125.7 (2)N22—N23—C23A108.39 (19)
C12—C13—C14120.0 (2)N23—C23A—C27A109.3 (2)
O13—C13—C14114.26 (18)N23—C23A—C24130.3 (2)
O14—C14—C15125.2 (2)C27A—C23A—C24120.4 (2)
O14—C14—C13115.4 (2)C25—C24—C23A117.1 (2)
C15—C14—C13119.44 (19)C25—C24—H24121.4
C16—C15—C14120.5 (2)C23A—C24—H24121.4
C16—C15—H15119.8C24—C25—C26121.6 (3)
C14—C15—H15119.8C24—C25—H25119.2
C11—C16—C15120.2 (2)C26—C25—H25119.2
C11—C16—H16119.9C27—C26—C25122.7 (3)
C15—C16—H16119.9C27—C26—H26118.6
C13—O13—C131117.62 (18)C25—C26—H26118.6
O13—C131—H13A109.5C26—C27—C27A114.8 (2)
O13—C131—H13B109.5C26—C27—H27122.6
H13A—C131—H13B109.5C27A—C27—H27122.6
O13—C131—H13C109.5N21—C27A—C23A102.4 (2)
H13A—C131—H13C109.5N21—C27A—C27134.2 (2)
H13B—C131—H13C109.5C23A—C27A—C27123.3 (2)
C14—O14—C141118.8 (2)
O1—C1—O2—N212.2 (3)C1—O2—N21—N2293.7 (2)
C11—C1—O2—N21177.67 (19)C1—O2—N21—C27A84.8 (3)
O1—C1—C11—C16178.9 (3)C27A—N21—N22—N231.5 (3)
O2—C1—C11—C161.2 (3)O2—N21—N22—N23179.79 (19)
O1—C1—C11—C122.4 (4)N21—N22—N23—C23A0.8 (3)
O2—C1—C11—C12177.50 (19)N22—N23—C23A—C27A0.1 (3)
C16—C11—C12—C130.5 (3)N22—N23—C23A—C24179.4 (2)
C1—C11—C12—C13178.2 (2)N23—C23A—C24—C25178.2 (3)
C11—C12—C13—O13178.8 (2)C27A—C23A—C24—C250.9 (4)
C11—C12—C13—C140.2 (3)C23A—C24—C25—C261.0 (4)
C12—C13—C14—O14178.9 (2)C24—C25—C26—C270.5 (5)
O13—C13—C14—O140.2 (3)C25—C26—C27—C27A0.1 (4)
C12—C13—C14—C150.5 (3)N22—N21—C27A—C23A1.5 (3)
O13—C13—C14—C15179.6 (2)O2—N21—C27A—C23A179.9 (2)
O14—C14—C15—C16178.5 (2)N22—N21—C27A—C27178.4 (3)
C13—C14—C15—C160.8 (4)O2—N21—C27A—C270.2 (4)
C12—C11—C16—C150.3 (3)N23—C23A—C27A—N211.0 (3)
C1—C11—C16—C15178.4 (2)C24—C23A—C27A—N21179.7 (2)
C14—C15—C16—C110.4 (4)N23—C23A—C27A—C27179.0 (2)
C12—C13—O13—C1311.1 (3)C24—C23A—C27A—C270.4 (4)
C14—C13—O13—C131178.0 (2)C26—C27—C27A—N21179.7 (3)
C15—C14—O14—C1416.0 (4)C26—C27—C27A—C23A0.2 (4)
C13—C14—O14—C141173.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···O14i0.932.523.175 (3)127
Symmetry code: (i) x+1, y+2, z+1.
Selected torsion angles (°) for compounds (I)–(VI) top
τ1τ2τ3τ4τ5
(I), major-0.7 (11)-179.0 (8)-163.2 (6)-103.8 (5)25.8 (8)
(I), minor-9(9)-158 (7)-158 (5)-97 (4)56 (4)
(II), major6.3 (15)179.1 (4)179.1 (9)-68.8 (7)-55.2 (5)
(II), minor14 (8)163 (6)-157 (5)-65 (3)49 (3)
(III), major-2(3)176.9 (18)146.9 (10)-71.2 (19)59 (2)
(III), minor14 (8)-159 (4)136 (4)-61 (5)33 (6)
(IV)0.5 (6)173.9 (4)142.0 (4)-123.7 (5)-177.8 (5)
(V)-4.5 (3)-170.4 (2)-16.1 (4)-111.7 (3)21.1 (4)
(VI), molecule 13.0 (6)-174.5 (4)137.2 (4)-110.7 (5)160.5 (4)
(VI), molecule 2, major4.5 (11)-174.3 (6)134.6 (7)-70.0 (7)-174.4 (6)
(VI), molecule 2, minor16 (11)172 (6)127 (8)-75 (6)105 (5)
For compounds (I)–(VI) τ1, τ2, τ3, τ4 and τ5 represent, respectively, the torsion angles Sx21—Cx22—Nx1—Cx1, Cx22—Nx1—Cx1—Cx11, Nx1—Cx1—Cx11—Cx12, Cx23—Cx37—Cx31—Cx32 and Sx21—Cx25—Cx26—Cx27. For (IV) and (V), x = nul; for the major- and minor-disorder components of (I), (II) and (III), x = 1 or 2, respectively; for compound (VI), x = 1 for molecule 1 and x = 2 or 3 for the major- and minor-disorder components, respectively, of molecule 2.
Hydrogen bonds and short intra- and intermolecular contacts (Å, °) for compounds (I)–(VII) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N11—H11···O1370.862.032.671 (12)131
N21—H21···O2370.862.122.73 (10)129
C115—H115···O137i0.932.533.438 (9)166
C215—H215···O237i0.932.133.04 (7)166
(II)N11—H11···O1370.862.082.719 (10)130
N21—H21···O2370.862.012.65 (5)131
C112—H112···O11ii0.932.473.230 (4)139
C144—H144···O137iii0.932.563.397 (6)150
(III)N11—H11···O1370.862.062.70 (2)131
N21—H21···O2370.862.122.71 (6)126
C114—H114···Cg1iv0.932.823.565 (12)138
C214—H214···O237v0.932.242.96 (4)134
(IV)N1—H1···O370.862.022.665 (5)131
C33—H33···O37vi0.932.443.322 (7)159
C15—H15···Cg2vii0.932.923.453 (6)118
(V)N1—H1···O120.861.972.651 (3)135
N1—H1···O370.862.082.716 (3)130
C13—H13···Cg2viii0.932.903.782 (4)158
C36—H36···O1ix0.932.483.306 (4)147
(VI)N11—H11···O1370.862.132.753 (4)129
N21—H21···O2370.862.102.733 (11)129
N31—H31···O3370.862.222.76 (10)121
N31—H31···O110.862.603.28 (10)137
C114—H114···O337x0.932.503.33 (5)150
C214—H214···O137xi0.932.593.407 (6)146
C314—H314···O137xi0.932.583.42 (4)150
(VII)C27—H27···O14ii0.932.523.175 (3)127
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) -x+1, y+1/2, -z+3/2; (iv) x, y+1, z; (v) -x+3/2, -y+3/2, -z+1; (vi) -x+3/2, y+1/2, -z+1/2; (vii) -x+3/2, y-1/2, -z+1/2; (viii) -x, -y, -z+1; (ix) -x, -y+1, -z+1; (x) x, -y+1, -z-1/2; (xi) x, -y+1, -z+1/2.

Cg1 and Cg2 represent the centroids of the C131–C136 and C31–C36 rings, respectively
 

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