Download citation
Download citation
link to html
Mol­ecules with well-defined structures that feature closely stacked aromatic rings are important for understanding π–π inter­actions. A previously reported C-shaped mol­ecule with bi­thio­phene-substituted quinoxaline rings suspended from an aliphatic bridge that holds the aromatic rings in close proximity exists as a pair of syn and anti diastereomers. The anti isomer, namely (1α,2β,4β,5α,16α,17β,19β,20α)-1,5,16,20-tetra­chloro-31,31,32,32-tetra­meth­oxy-11,26-bis­[5-(thio­phen-2-yl)thio­phen-2-yl]-7,14,22,29-tetra­aza­nona­cyclo­[18.10.1.15,16.02,19.04,17.06,15.08,13.021,30.023,28]dotriaconta-6(15),7,9,11,13,21(30),22,24,26,28-deca­ene chloro­form monosolvate, C48H36Cl4N4O4S4·CHCl3, whose X-ray structure is described herein, has cofacial quinoxaline rings with bi­thio­phene rings attached on opposite sides. The mol­ecular structure is approximately C-shaped and consists of an aliphatic spacer with a boat-shaped cyclo­hexane ring in the middle. The centroid-to-centroid distance between the quinoxaline rings is 3.950 (1) Å, with ring-offset distances of 0.354 (3) and 0.816 (2) Å. The pendant bi­thio­phene rings are oriented parallel to one another, which results from the thio­phene rings connected to the quinoxaline rings being oriented such that their S atoms are rotated inward toward one another, but are not overlapped. Inter­molecular packing is largely governed by van der Waals forces and a few weak C—H...X (X = N or O) inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617001991/fn3230sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617001991/fn3230Isup2.hkl
Contains datablock I

CCDC reference: 1531502

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(1α,2β,4β,5α,16α,17β,19β,20α)-1,5,16,20-Tetrachloro-31,31,32,32-tetramethoxy-11,26-bis[5-(thiophen-2-yl)thiophen-2-yl]-7,14,22,29-tetraazanonacyclo[18.10.1.15,16.02,19.04,17.06,15.08,13.021,30.023,28]dotriaconta-6(15),7,9,11,13,21(30),22,24,26,28-decaene chloroform monosolvate top
Crystal data top
C48H36Cl4N4O4S4·CHCl3Z = 2
Mr = 1122.21F(000) = 1148
Triclinic, P1Dx = 1.550 Mg m3
a = 10.242 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.8070 (11) ÅCell parameters from 9947 reflections
c = 22.297 (2) Åθ = 2.2–30.5°
α = 80.453 (2)°µ = 0.64 mm1
β = 84.916 (2)°T = 125 K
γ = 64.733 (1)°Block, yellow
V = 2404.1 (4) Å30.40 × 0.34 × 0.25 mm
Data collection top
Bruker APEXII CCD
diffractometer
24744 independent reflections
Radiation source: fine-focus sealed tube20204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.3333 pixels mm-1θmax = 30.6°, θmin = 0.9°
φ and ω scansh = 1414
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2012)
k = 1616
Tmin = 0.77, Tmax = 0.86l = 031
33271 measured reflections
Refinement top
Refinement on F2220 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.9895P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
24744 reflectionsΔρmax = 0.48 e Å3
731 parametersΔρmin = 0.43 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refined as a two-component twin, BASF = 0.1428 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.06975 (5)0.16846 (5)0.84603 (2)0.02827 (10)
Cl20.64609 (5)0.08870 (4)0.86474 (2)0.02904 (10)
Cl30.13500 (4)0.69821 (4)0.92139 (2)0.02556 (9)
Cl40.44435 (4)0.62536 (4)0.92841 (2)0.02180 (8)
S10.24021 (5)0.63431 (5)0.48306 (2)0.02701 (10)
S20.05378 (6)0.85002 (6)0.33618 (2)0.03690 (12)
S30.25509 (5)0.92933 (5)0.52407 (2)0.02798 (10)
O20.40755 (14)0.00445 (12)0.82380 (6)0.0236 (3)
O30.12252 (14)0.65417 (13)1.00497 (6)0.0241 (3)
O40.11863 (14)0.81689 (12)0.92913 (6)0.0252 (3)
N10.18362 (15)0.31846 (14)0.74103 (6)0.0192 (3)
N20.48151 (15)0.27466 (14)0.74938 (7)0.0205 (3)
N30.02319 (15)0.71952 (14)0.79352 (7)0.0199 (3)
N40.32301 (16)0.67316 (14)0.79927 (7)0.0204 (3)
C10.0312 (3)0.9216 (2)0.28415 (9)0.0372 (5)
H1A0.00580.96460.24520.045*
C20.1566 (3)0.9096 (2)0.30506 (10)0.0356 (5)
H2A0.21850.94280.28230.043*
C30.1858 (2)0.84228 (18)0.36454 (9)0.0268 (4)
H3B0.26940.8260.38610.032*
C40.0811 (2)0.80271 (18)0.38808 (8)0.0248 (4)
C50.0800 (2)0.72465 (18)0.44559 (8)0.0248 (3)
C60.0312 (2)0.7069 (2)0.47753 (10)0.0374 (5)
H6A0.12820.74760.46430.045*
C70.0117 (2)0.6221 (2)0.53233 (10)0.0361 (5)
H7A0.05390.60060.55940.043*
C80.15654 (19)0.57398 (18)0.54254 (8)0.0233 (3)
C90.23976 (18)0.49052 (17)0.59513 (8)0.0209 (3)
C100.17590 (18)0.43848 (17)0.64232 (8)0.0213 (3)
H10A0.07810.45240.63940.026*
C110.25356 (17)0.36544 (16)0.69443 (7)0.0187 (3)
C120.40085 (17)0.34297 (16)0.69886 (8)0.0190 (3)
C130.46561 (18)0.39438 (18)0.65003 (8)0.0230 (3)
H13A0.56390.37970.6520.028*
C140.38736 (19)0.46518 (18)0.59989 (8)0.0245 (4)
H14A0.4330.49840.56730.029*
C150.26456 (18)0.25420 (16)0.78758 (8)0.0189 (3)
C160.41128 (18)0.23275 (16)0.79183 (8)0.0194 (3)
C170.45759 (19)0.16487 (16)0.85484 (8)0.0210 (3)
C180.3717 (2)0.08022 (17)0.86468 (8)0.0238 (3)
O10.3367 (6)0.0334 (5)0.9226 (2)0.0228 (10)0.359 (4)
C190.4582 (7)0.0726 (5)0.9493 (3)0.0319 (13)0.359 (4)
H19A0.42510.12430.98030.048*0.359 (4)
H19B0.51850.04310.96820.048*0.359 (4)
H19C0.51480.12360.91780.048*0.359 (4)
C200.3406 (6)0.0804 (5)0.8189 (2)0.0283 (12)0.359 (4)
H20A0.26930.04030.78660.042*0.359 (4)
H20B0.29190.09330.85750.042*0.359 (4)
H20C0.41250.16230.80890.042*0.359 (4)
O1'0.3993 (3)0.0219 (3)0.92557 (13)0.0220 (5)0.641 (4)
C19'0.3192 (4)0.0519 (3)0.94704 (14)0.0293 (7)0.641 (4)
H19D0.36460.11060.98340.044*0.641 (4)
H19E0.31860.09990.91530.044*0.641 (4)
H19F0.21980.00450.95710.044*0.641 (4)
C20'0.5408 (3)0.1190 (3)0.82973 (14)0.0286 (7)0.641 (4)
H20D0.6180.10280.80610.043*0.641 (4)
H20E0.52720.18640.81450.043*0.641 (4)
H20F0.56720.14510.87260.043*0.641 (4)
C210.22458 (19)0.19741 (16)0.84809 (8)0.0209 (3)
C220.21533 (19)0.28239 (16)0.89595 (7)0.0194 (3)
H22A0.18360.24860.93590.023*
C230.37737 (19)0.25966 (16)0.90045 (8)0.0203 (3)
H23A0.41140.21690.94230.024*
C240.11361 (17)0.42164 (16)0.88001 (8)0.0188 (3)
H24A0.01230.43170.88240.023*
H24B0.13420.45320.83790.023*
C250.13433 (17)0.49776 (15)0.92437 (7)0.0175 (3)
H25A0.10.47280.96570.021*
C260.29587 (18)0.47549 (15)0.92857 (7)0.0176 (3)
H26A0.32680.44370.97170.021*
C270.39884 (17)0.38148 (15)0.88810 (8)0.0192 (3)
H27A0.38010.41840.84480.023*
H27B0.49980.3630.89650.023*
C280.05305 (17)0.64362 (16)0.90717 (7)0.0183 (3)
C290.14072 (18)0.69087 (16)0.94353 (8)0.0199 (3)
C300.2088 (2)0.6755 (2)1.04588 (9)0.0302 (4)
H30A0.17330.66441.08770.045*
H30B0.20180.76171.03520.045*
H30C0.30970.61471.04250.045*
C310.0225 (2)0.9090 (2)0.94127 (14)0.0467 (6)
H31A0.01940.99090.94090.07*
H31B0.05680.88280.98130.07*
H31C0.08820.91650.910.07*
C320.28721 (17)0.61062 (15)0.91169 (7)0.0175 (3)
C330.24482 (17)0.65689 (15)0.84598 (7)0.0176 (3)
C340.09688 (17)0.67921 (15)0.84320 (7)0.0178 (3)
C350.10194 (18)0.73831 (16)0.74225 (8)0.0201 (3)
C360.0332 (2)0.78411 (18)0.68580 (8)0.0248 (4)
H36A0.06510.7990.68330.03*
C370.1065 (2)0.80736 (18)0.63444 (8)0.0257 (4)
H37A0.05820.83920.59680.031*
C380.2535 (2)0.78464 (18)0.63667 (8)0.0248 (4)
C390.3232 (2)0.73877 (18)0.69159 (8)0.0244 (4)
H39A0.4220.72290.69320.029*
C400.24969 (19)0.71530 (17)0.74510 (8)0.0205 (3)
C410.3342 (2)0.80598 (19)0.58171 (8)0.0268 (4)
C420.4758 (2)0.7356 (2)0.56764 (10)0.0365 (5)
H42A0.53770.66350.59360.044*
C430.5209 (2)0.7809 (2)0.51077 (10)0.0377 (5)
H43A0.61590.74170.49440.045*
C440.4144 (2)0.8867 (2)0.48155 (8)0.0277 (4)
S40.57675 (19)0.90679 (15)0.38103 (6)0.0408 (4)0.575 (3)
C450.4180 (19)0.9634 (15)0.4237 (5)0.025 (2)0.575 (3)
C460.3251 (12)1.0737 (11)0.3960 (5)0.066 (4)0.575 (3)
H46A0.23531.12420.41370.079*0.575 (3)
C470.3735 (14)1.1084 (13)0.3375 (7)0.051 (3)0.575 (3)
H47A0.31491.1780.30940.062*0.575 (3)
C480.5137 (13)1.0306 (9)0.3260 (5)0.0381 (17)0.575 (3)
H48A0.56851.04470.29120.046*0.575 (3)
S4'0.3032 (3)1.1024 (3)0.39839 (12)0.0306 (5)0.425 (3)
C45'0.434 (3)0.952 (2)0.4225 (8)0.029 (3)0.425 (3)
C46'0.5230 (8)0.9178 (9)0.3740 (4)0.0426 (19)0.425 (3)
H46B0.59480.83360.37440.051*0.425 (3)
C47'0.508 (2)1.0047 (14)0.3255 (9)0.052 (4)0.425 (3)
H47B0.56980.99010.29060.062*0.425 (3)
C48'0.3943 (17)1.1160 (15)0.3315 (8)0.036 (2)0.425 (3)
H48B0.36881.19080.30280.044*0.425 (3)
C1S0.8255 (17)0.4480 (13)0.7390 (7)0.028 (3)0.50 (2)
H1SA0.92280.3750.74070.034*0.50 (2)
Cl50.8389 (7)0.5715 (4)0.7696 (3)0.0461 (9)0.50 (2)
Cl60.7022 (7)0.3959 (9)0.7793 (4)0.0655 (12)0.50 (2)
Cl70.7773 (5)0.4994 (4)0.6627 (2)0.0303 (7)0.50 (2)
C1S'0.8198 (16)0.4542 (13)0.7438 (7)0.032 (3)0.50 (2)
H1SB0.92320.39160.74680.038*0.50 (2)
Cl5'0.7932 (12)0.5738 (4)0.7853 (4)0.0614 (14)0.50 (2)
Cl6'0.7109 (5)0.3774 (3)0.7724 (3)0.0386 (8)0.50 (2)
Cl7'0.7791 (6)0.5154 (8)0.6656 (3)0.0607 (12)0.50 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0380 (2)0.0321 (2)0.0271 (2)0.0268 (2)0.00168 (17)0.00452 (18)
Cl20.0273 (2)0.0229 (2)0.0284 (2)0.00161 (17)0.00840 (17)0.00173 (17)
Cl30.01983 (18)0.0280 (2)0.0267 (2)0.00833 (16)0.00043 (15)0.00346 (17)
Cl40.02329 (18)0.01991 (19)0.02506 (19)0.01153 (15)0.00819 (15)0.00018 (15)
S10.0229 (2)0.0336 (2)0.0202 (2)0.01025 (18)0.00310 (15)0.00462 (18)
S20.0432 (3)0.0383 (3)0.0312 (3)0.0195 (2)0.0190 (2)0.0061 (2)
S30.0343 (2)0.0275 (2)0.0184 (2)0.01147 (19)0.00052 (17)0.00221 (17)
O20.0276 (6)0.0173 (6)0.0235 (6)0.0058 (5)0.0037 (5)0.0049 (5)
O30.0297 (6)0.0269 (7)0.0170 (6)0.0119 (5)0.0016 (5)0.0051 (5)
O40.0275 (6)0.0133 (6)0.0336 (7)0.0062 (5)0.0073 (5)0.0031 (5)
N10.0209 (6)0.0209 (7)0.0188 (7)0.0115 (6)0.0011 (5)0.0025 (5)
N20.0209 (6)0.0200 (7)0.0210 (7)0.0088 (6)0.0046 (5)0.0013 (5)
N30.0218 (6)0.0175 (7)0.0205 (7)0.0087 (5)0.0051 (5)0.0009 (5)
N40.0231 (7)0.0205 (7)0.0188 (7)0.0114 (6)0.0056 (5)0.0033 (5)
C10.0590 (14)0.0280 (10)0.0216 (9)0.0149 (10)0.0092 (9)0.0001 (8)
C20.0491 (12)0.0284 (10)0.0266 (10)0.0149 (9)0.0027 (9)0.0024 (8)
C30.0288 (9)0.0242 (9)0.0257 (9)0.0095 (7)0.0028 (7)0.0020 (7)
C40.0280 (9)0.0235 (9)0.0201 (8)0.0077 (7)0.0066 (7)0.0017 (7)
C50.0252 (8)0.0249 (9)0.0222 (8)0.0087 (7)0.0069 (6)0.0006 (7)
C60.0247 (9)0.0455 (13)0.0354 (11)0.0131 (9)0.0105 (8)0.0124 (9)
C70.0253 (9)0.0451 (13)0.0329 (10)0.0152 (9)0.0052 (8)0.0116 (9)
C80.0237 (8)0.0265 (9)0.0196 (8)0.0115 (7)0.0010 (6)0.0003 (7)
C90.0203 (7)0.0238 (8)0.0174 (7)0.0082 (6)0.0030 (6)0.0011 (6)
C100.0186 (7)0.0261 (9)0.0196 (8)0.0099 (7)0.0023 (6)0.0015 (6)
C110.0181 (7)0.0208 (8)0.0182 (7)0.0092 (6)0.0008 (6)0.0026 (6)
C120.0185 (7)0.0202 (8)0.0184 (7)0.0082 (6)0.0021 (6)0.0017 (6)
C130.0178 (7)0.0282 (9)0.0228 (8)0.0108 (7)0.0012 (6)0.0004 (7)
C140.0223 (8)0.0296 (9)0.0207 (8)0.0119 (7)0.0003 (6)0.0014 (7)
C150.0235 (8)0.0174 (7)0.0186 (7)0.0111 (6)0.0002 (6)0.0034 (6)
C160.0227 (8)0.0171 (8)0.0196 (8)0.0090 (6)0.0054 (6)0.0014 (6)
C170.0253 (8)0.0160 (7)0.0203 (8)0.0071 (6)0.0066 (6)0.0003 (6)
C180.0379 (10)0.0168 (8)0.0188 (8)0.0137 (7)0.0026 (7)0.0009 (6)
O10.034 (3)0.0155 (19)0.0167 (18)0.010 (2)0.005 (2)0.0029 (14)
C190.045 (3)0.020 (3)0.029 (3)0.013 (2)0.013 (2)0.005 (2)
C200.040 (3)0.022 (3)0.027 (3)0.017 (2)0.004 (2)0.004 (2)
O1'0.0272 (13)0.0169 (11)0.0207 (11)0.0089 (12)0.0052 (11)0.0022 (8)
C19'0.0407 (17)0.0204 (14)0.0283 (15)0.0164 (13)0.0015 (12)0.0014 (11)
C20'0.0289 (14)0.0191 (14)0.0290 (15)0.0005 (11)0.0037 (11)0.0057 (11)
C210.0301 (8)0.0193 (8)0.0189 (8)0.0161 (7)0.0002 (6)0.0017 (6)
C220.0278 (8)0.0175 (8)0.0169 (7)0.0137 (7)0.0000 (6)0.0011 (6)
C230.0264 (8)0.0164 (7)0.0185 (8)0.0089 (6)0.0065 (6)0.0000 (6)
C240.0197 (7)0.0193 (8)0.0204 (8)0.0111 (6)0.0008 (6)0.0026 (6)
C250.0206 (7)0.0164 (7)0.0163 (7)0.0092 (6)0.0007 (6)0.0004 (6)
C260.0227 (7)0.0142 (7)0.0163 (7)0.0085 (6)0.0053 (6)0.0012 (6)
C270.0191 (7)0.0159 (7)0.0229 (8)0.0072 (6)0.0048 (6)0.0018 (6)
C280.0187 (7)0.0181 (8)0.0189 (7)0.0086 (6)0.0012 (6)0.0019 (6)
C290.0248 (8)0.0154 (7)0.0195 (8)0.0081 (6)0.0040 (6)0.0014 (6)
C300.0305 (9)0.0383 (11)0.0217 (9)0.0112 (8)0.0039 (7)0.0112 (8)
C310.0309 (11)0.0187 (10)0.086 (2)0.0033 (8)0.0051 (11)0.0142 (11)
C320.0198 (7)0.0158 (7)0.0184 (7)0.0087 (6)0.0054 (6)0.0007 (6)
C330.0203 (7)0.0147 (7)0.0183 (7)0.0084 (6)0.0054 (6)0.0014 (6)
C340.0205 (7)0.0140 (7)0.0194 (7)0.0083 (6)0.0022 (6)0.0002 (6)
C350.0242 (8)0.0187 (8)0.0186 (7)0.0108 (6)0.0047 (6)0.0012 (6)
C360.0245 (8)0.0274 (9)0.0217 (8)0.0107 (7)0.0072 (6)0.0015 (7)
C370.0295 (9)0.0273 (9)0.0194 (8)0.0119 (7)0.0075 (7)0.0026 (7)
C380.0309 (9)0.0258 (9)0.0190 (8)0.0146 (7)0.0039 (7)0.0025 (7)
C390.0262 (8)0.0293 (9)0.0200 (8)0.0155 (7)0.0044 (6)0.0032 (7)
C400.0247 (8)0.0201 (8)0.0181 (7)0.0119 (7)0.0050 (6)0.0028 (6)
C410.0319 (9)0.0311 (10)0.0187 (8)0.0160 (8)0.0057 (7)0.0038 (7)
C420.0291 (10)0.0464 (13)0.0287 (10)0.0158 (9)0.0064 (8)0.0114 (9)
C430.0282 (10)0.0515 (14)0.0300 (10)0.0178 (10)0.0028 (8)0.0070 (9)
C440.0325 (9)0.0366 (11)0.0201 (8)0.0214 (8)0.0021 (7)0.0003 (7)
S40.0510 (10)0.0404 (7)0.0270 (6)0.0181 (7)0.0108 (6)0.0030 (4)
C450.032 (4)0.041 (5)0.014 (3)0.026 (4)0.003 (2)0.004 (2)
C460.048 (4)0.076 (7)0.057 (5)0.022 (4)0.009 (3)0.020 (4)
C470.053 (4)0.067 (5)0.044 (4)0.044 (3)0.019 (3)0.029 (3)
C480.053 (3)0.056 (4)0.018 (2)0.038 (3)0.0019 (18)0.002 (2)
S4'0.0307 (9)0.0361 (10)0.0222 (7)0.0140 (8)0.0062 (6)0.0060 (6)
C45'0.031 (5)0.027 (4)0.029 (5)0.012 (3)0.011 (3)0.004 (3)
C46'0.025 (3)0.050 (4)0.058 (4)0.019 (3)0.006 (3)0.018 (3)
C47'0.063 (6)0.066 (6)0.035 (4)0.036 (5)0.009 (4)0.008 (4)
C48'0.046 (5)0.043 (4)0.030 (4)0.035 (4)0.006 (3)0.016 (3)
C1S0.026 (5)0.026 (4)0.043 (5)0.017 (3)0.001 (3)0.017 (4)
Cl50.0513 (16)0.0285 (7)0.0588 (17)0.0106 (9)0.0310 (11)0.0082 (9)
Cl60.0475 (18)0.114 (3)0.0471 (14)0.053 (2)0.0009 (12)0.010 (2)
Cl70.0245 (10)0.0368 (12)0.0301 (11)0.0119 (7)0.0089 (7)0.0045 (8)
C1S'0.022 (4)0.039 (6)0.027 (4)0.010 (4)0.014 (3)0.014 (4)
Cl5'0.077 (3)0.0364 (9)0.078 (2)0.0256 (15)0.040 (2)0.0038 (12)
Cl6'0.0283 (9)0.0331 (15)0.057 (2)0.0176 (9)0.0012 (9)0.0010 (9)
Cl7'0.0332 (12)0.090 (3)0.0430 (19)0.0201 (17)0.0067 (12)0.0200 (17)
Geometric parameters (Å, º) top
Cl1—C211.7648 (18)C21—C221.553 (2)
Cl2—C171.7642 (18)C22—C241.525 (2)
Cl3—C281.7679 (17)C22—C231.574 (2)
Cl4—C321.7681 (16)C22—H22A1.0
S1—C51.7267 (18)C23—C271.523 (2)
S1—C81.7341 (18)C23—H23A1.0
S2—C11.715 (2)C24—C251.525 (2)
S2—C41.7234 (18)C24—H24A0.99
S3—C411.7279 (19)C24—H24B0.99
S3—C441.732 (2)C25—C281.556 (2)
O2—C201.363 (5)C25—C261.569 (2)
O2—C181.377 (2)C25—H25A1.0
O2—C20'1.451 (3)C26—C271.524 (2)
O3—C291.388 (2)C26—C321.543 (2)
O3—C301.444 (2)C26—H26A1.0
O4—C291.391 (2)C27—H27A0.99
O4—C311.425 (2)C27—H27B0.99
N1—C151.302 (2)C28—C341.504 (2)
N1—C111.384 (2)C28—C291.575 (2)
N2—C161.298 (2)C29—C321.573 (2)
N2—C121.377 (2)C30—H30A0.98
N3—C341.300 (2)C30—H30B0.98
N3—C351.383 (2)C30—H30C0.98
N4—C331.296 (2)C31—H31A0.98
N4—C401.383 (2)C31—H31B0.98
C1—C21.348 (3)C31—H31C0.98
C1—H1A0.95C32—C331.509 (2)
C2—C31.413 (3)C33—C341.428 (2)
C2—H2A0.95C35—C361.407 (2)
C3—C41.374 (3)C35—C401.424 (2)
C3—H3B0.95C36—C371.368 (3)
C4—C51.452 (3)C36—H36A0.95
C5—C61.363 (3)C37—C381.416 (3)
C6—C71.415 (3)C37—H37A0.95
C6—H6A0.95C38—C391.381 (2)
C7—C81.369 (3)C38—C411.464 (3)
C7—H7A0.95C39—C401.406 (2)
C8—C91.466 (2)C39—H39A0.95
C9—C101.385 (2)C41—C421.368 (3)
C9—C141.421 (2)C42—C431.410 (3)
C10—C111.404 (2)C42—H42A0.95
C10—H10A0.95C43—C441.367 (3)
C11—C121.426 (2)C43—H43A0.95
C12—C131.411 (2)C44—C451.454 (9)
C13—C141.367 (2)C44—C45'1.456 (14)
C13—H13A0.95S4—C481.673 (10)
C14—H14A0.95S4—C451.734 (15)
C15—C161.423 (2)C45—C461.328 (19)
C15—C211.508 (2)C46—C471.413 (15)
C16—C171.504 (2)C46—H46A0.95
C17—C231.551 (2)C47—C481.364 (11)
C17—C181.570 (2)C47—H47A0.95
C18—O11.397 (5)C48—H48A0.95
C18—O1'1.410 (3)S4'—C48'1.710 (14)
C18—C211.572 (3)S4'—C45'1.74 (2)
O1—C191.423 (7)C45'—C46'1.35 (2)
C19—H19A0.98C46'—C47'1.331 (17)
C19—H19B0.98C46'—H46B0.95
C19—H19C0.98C47'—C48'1.350 (14)
C20—H20A0.98C47'—H47B0.95
C20—H20B0.98C48'—H48B0.95
C20—H20C0.98C1S—Cl71.748 (16)
O1'—C19'1.436 (4)C1S—Cl61.750 (16)
C19'—H19D0.98C1S—Cl51.768 (13)
C19'—H19E0.98C1S—H1SA1.0
C19'—H19F0.98C1S'—Cl5'1.728 (16)
C20'—H20D0.98C1S'—Cl6'1.736 (16)
C20'—H20E0.98C1S'—Cl7'1.788 (14)
C20'—H20F0.98C1S'—H1SB1.0
C5—S1—C892.85 (9)C24—C25—C28114.23 (13)
C1—S2—C492.03 (10)C24—C25—C26113.01 (13)
C41—S3—C4492.15 (10)C28—C25—C26103.65 (12)
C20—O2—C18126.0 (3)C24—C25—H25A108.6
C18—O2—C20'120.52 (17)C28—C25—H25A108.6
C29—O3—C30115.94 (14)C26—C25—H25A108.6
C29—O4—C31116.33 (16)C27—C26—C32114.15 (13)
C15—N1—C11113.74 (14)C27—C26—C25113.37 (13)
C16—N2—C12113.83 (14)C32—C26—C25102.41 (12)
C34—N3—C35113.68 (14)C27—C26—H26A108.9
C33—N4—C40113.67 (14)C32—C26—H26A108.9
C2—C1—S2111.95 (16)C25—C26—H26A108.9
C2—C1—H1A124.0C23—C27—C26109.65 (14)
S2—C1—H1A124.0C23—C27—H27A109.7
C1—C2—C3112.6 (2)C26—C27—H27A109.7
C1—C2—H2A123.7C23—C27—H27B109.7
C3—C2—H2A123.7C26—C27—H27B109.7
C4—C3—C2113.25 (18)H27A—C27—H27B108.2
C4—C3—H3B123.4C34—C28—C25108.28 (13)
C2—C3—H3B123.4C34—C28—C2999.91 (13)
C3—C4—C5128.34 (17)C25—C28—C29101.05 (13)
C3—C4—S2110.16 (14)C34—C28—Cl3115.45 (12)
C5—C4—S2121.36 (14)C25—C28—Cl3112.19 (11)
C6—C5—C4130.48 (17)C29—C28—Cl3118.33 (12)
C6—C5—S1110.23 (14)O3—C29—O4113.83 (14)
C4—C5—S1119.28 (14)O3—C29—C32117.69 (14)
C5—C6—C7113.58 (18)O4—C29—C32106.73 (13)
C5—C6—H6A123.2O3—C29—C28107.44 (13)
C7—C6—H6A123.2O4—C29—C28117.49 (14)
C8—C7—C6113.55 (18)C32—C29—C2892.21 (12)
C8—C7—H7A123.2O3—C30—H30A109.5
C6—C7—H7A123.2O3—C30—H30B109.5
C7—C8—C9129.79 (17)H30A—C30—H30B109.5
C7—C8—S1109.78 (14)O3—C30—H30C109.5
C9—C8—S1120.33 (13)H30A—C30—H30C109.5
C10—C9—C14118.35 (15)H30B—C30—H30C109.5
C10—C9—C8121.24 (15)O4—C31—H31A109.5
C14—C9—C8120.36 (15)O4—C31—H31B109.5
C9—C10—C11121.01 (15)H31A—C31—H31B109.5
C9—C10—H10A119.5O4—C31—H31C109.5
C11—C10—H10A119.5H31A—C31—H31C109.5
N1—C11—C10118.75 (14)H31B—C31—H31C109.5
N1—C11—C12121.43 (15)C33—C32—C26108.77 (13)
C10—C11—C12119.81 (15)C33—C32—C2999.58 (13)
N2—C12—C13118.83 (15)C26—C32—C29101.72 (13)
N2—C12—C11122.46 (15)C33—C32—Cl4112.90 (11)
C13—C12—C11118.70 (15)C26—C32—Cl4114.13 (11)
C14—C13—C12120.22 (15)C29—C32—Cl4118.22 (11)
C14—C13—H13A119.9N4—C33—C34124.35 (15)
C12—C13—H13A119.9N4—C33—C32128.93 (15)
C13—C14—C9121.89 (16)C34—C33—C32106.71 (14)
C13—C14—H14A119.1N3—C34—C33124.24 (15)
C9—C14—H14A119.1N3—C34—C28130.07 (15)
N1—C15—C16124.53 (15)C33—C34—C28105.66 (14)
N1—C15—C21129.22 (15)N3—C35—C36119.00 (15)
C16—C15—C21106.09 (14)N3—C35—C40121.96 (15)
N2—C16—C15124.01 (15)C36—C35—C40119.02 (16)
N2—C16—C17129.43 (15)C37—C36—C35120.61 (17)
C15—C16—C17106.37 (14)C37—C36—H36A119.7
C16—C17—C23107.87 (14)C35—C36—H36A119.7
C16—C17—C18100.46 (13)C36—C37—C38120.89 (16)
C23—C17—C18101.02 (14)C36—C37—H37A119.6
C16—C17—Cl2114.85 (13)C38—C37—H37A119.6
C23—C17—Cl2113.32 (12)C39—C38—C37119.36 (16)
C18—C17—Cl2117.66 (12)C39—C38—C41119.24 (17)
O2—C18—O1112.9 (2)C37—C38—C41121.39 (16)
O2—C18—O1'113.47 (18)C38—C39—C40120.78 (16)
O2—C18—C17114.26 (15)C38—C39—H39A119.6
O1—C18—C17122.3 (3)C40—C39—H39A119.6
O1'—C18—C17103.74 (17)N4—C40—C39118.56 (15)
O2—C18—C21111.05 (14)N4—C40—C35122.09 (15)
O1—C18—C21100.2 (2)C39—C40—C35119.33 (15)
O1'—C18—C21119.99 (18)C42—C41—C38127.27 (18)
C17—C18—C2192.23 (13)C42—C41—S3110.66 (14)
C18—O1—C19111.1 (4)C38—C41—S3122.07 (15)
O1—C19—H19A109.5C41—C42—C43113.29 (19)
O1—C19—H19B109.5C41—C42—H42A123.4
H19A—C19—H19B109.5C43—C42—H42A123.4
O1—C19—H19C109.5C44—C43—C42113.32 (19)
H19A—C19—H19C109.5C44—C43—H43A123.3
H19B—C19—H19C109.5C42—C43—H43A123.3
O2—C20—H20A109.5C43—C44—C45130.3 (7)
O2—C20—H20B109.5C43—C44—C45'123.9 (10)
H20A—C20—H20B109.5C43—C44—S3110.57 (14)
O2—C20—H20C109.5C45—C44—S3119.1 (7)
H20A—C20—H20C109.5C45'—C44—S3125.5 (9)
H20B—C20—H20C109.5C48—S4—C4592.5 (6)
C18—O1'—C19'113.8 (2)C46—C45—C44133.5 (13)
O1'—C19'—H19D109.5C46—C45—S4110.3 (7)
O1'—C19'—H19E109.5C44—C45—S4116.1 (10)
H19D—C19'—H19E109.5C45—C46—C47113.2 (11)
O1'—C19'—H19F109.5C45—C46—H46A123.4
H19D—C19'—H19F109.5C47—C46—H46A123.4
H19E—C19'—H19F109.5C48—C47—C46112.3 (12)
O2—C20'—H20D109.5C48—C47—H47A123.9
O2—C20'—H20E109.5C46—C47—H47A123.9
H20D—C20'—H20E109.5C47—C48—S4111.1 (9)
O2—C20'—H20F109.5C47—C48—H48A124.4
H20D—C20'—H20F109.5S4—C48—H48A124.4
H20E—C20'—H20F109.5C48'—S4'—C45'92.5 (8)
C15—C21—C22107.74 (13)C46'—C45'—C44134.8 (17)
C15—C21—C18100.61 (14)C46'—C45'—S4'105.7 (9)
C22—C21—C18101.31 (13)C44—C45'—S4'118.6 (14)
C15—C21—Cl1113.72 (12)C47'—C46'—C45'118.4 (13)
C22—C21—Cl1114.24 (12)C47'—C46'—H46B120.8
C18—C21—Cl1117.61 (12)C45'—C46'—H46B120.8
C24—C22—C21114.79 (14)C46'—C47'—C48'112.4 (16)
C24—C22—C23113.07 (13)C46'—C47'—H47B123.8
C21—C22—C23102.47 (13)C48'—C47'—H47B123.8
C24—C22—H22A108.7C47'—C48'—S4'109.9 (13)
C21—C22—H22A108.7C47'—C48'—H48B125.0
C23—C22—H22A108.7S4'—C48'—H48B125.0
C27—C23—C17114.53 (14)Cl7—C1S—Cl6110.3 (7)
C27—C23—C22113.15 (14)Cl7—C1S—Cl5109.0 (7)
C17—C23—C22103.25 (13)Cl6—C1S—Cl5112.7 (10)
C27—C23—H23A108.5Cl7—C1S—H1SA108.2
C17—C23—H23A108.5Cl6—C1S—H1SA108.2
C22—C23—H23A108.5Cl5—C1S—H1SA108.2
C22—C24—C25109.42 (13)Cl5'—C1S'—Cl6'110.5 (10)
C22—C24—H24A109.8Cl5'—C1S'—Cl7'111.0 (7)
C25—C24—H24A109.8Cl6'—C1S'—Cl7'108.7 (7)
C22—C24—H24B109.8Cl5'—C1S'—H1SB108.9
C25—C24—H24B109.8Cl6'—C1S'—H1SB108.9
H24A—C24—H24B108.2Cl7'—C1S'—H1SB108.9
C4—S2—C1—C20.30 (18)C28—C25—C26—C27124.84 (14)
S2—C1—C2—C30.5 (2)C24—C25—C26—C32122.81 (14)
C1—C2—C3—C40.5 (3)C28—C25—C26—C321.38 (15)
C2—C3—C4—C5175.47 (19)C17—C23—C27—C26170.41 (13)
C2—C3—C4—S20.2 (2)C22—C23—C27—C2652.44 (18)
C1—S2—C4—C30.03 (16)C32—C26—C27—C23169.01 (13)
C1—S2—C4—C5176.08 (17)C25—C26—C27—C2352.25 (17)
C3—C4—C5—C6162.6 (2)C24—C25—C28—C3454.47 (17)
S2—C4—C5—C622.1 (3)C26—C25—C28—C3468.93 (15)
C3—C4—C5—S118.2 (3)C24—C25—C28—C29158.91 (13)
S2—C4—C5—S1157.02 (12)C26—C25—C28—C2935.51 (15)
C8—S1—C5—C60.75 (18)C24—C25—C28—Cl374.09 (15)
C8—S1—C5—C4179.95 (16)C26—C25—C28—Cl3162.51 (11)
C4—C5—C6—C7179.9 (2)C30—O3—C29—O455.3 (2)
S1—C5—C6—C70.7 (3)C30—O3—C29—C3270.70 (19)
C5—C6—C7—C80.2 (3)C30—O3—C29—C28172.85 (14)
C6—C7—C8—C9175.9 (2)C31—O4—C29—O362.4 (2)
C6—C7—C8—S10.4 (3)C31—O4—C29—C32166.09 (17)
C5—S1—C8—C70.64 (17)C31—O4—C29—C2864.4 (2)
C5—S1—C8—C9176.07 (16)C34—C28—C29—O3174.58 (13)
C7—C8—C9—C105.9 (3)C25—C28—C29—O363.57 (15)
S1—C8—C9—C10178.17 (14)Cl3—C28—C29—O359.27 (17)
C7—C8—C9—C14171.6 (2)C34—C28—C29—O455.56 (18)
S1—C8—C9—C144.3 (2)C25—C28—C29—O4166.57 (14)
C14—C9—C10—C111.8 (3)Cl3—C28—C29—O470.59 (18)
C8—C9—C10—C11175.74 (17)C34—C28—C29—C3254.62 (13)
C15—N1—C11—C10178.77 (16)C25—C28—C29—C3256.39 (13)
C15—N1—C11—C120.1 (2)Cl3—C28—C29—C32179.24 (11)
C9—C10—C11—N1178.24 (16)C27—C26—C32—C3356.47 (17)
C9—C10—C11—C120.7 (3)C25—C26—C32—C3366.47 (15)
C16—N2—C12—C13179.34 (16)C27—C26—C32—C29160.94 (13)
C16—N2—C12—C110.4 (2)C25—C26—C32—C2938.00 (15)
N1—C11—C12—N20.5 (3)C27—C26—C32—Cl470.58 (16)
C10—C11—C12—N2178.44 (16)C25—C26—C32—Cl4166.48 (11)
N1—C11—C12—C13179.44 (16)O3—C29—C32—C33164.58 (14)
C10—C11—C12—C130.5 (3)O4—C29—C32—C3366.06 (15)
N2—C12—C13—C14178.42 (17)C28—C29—C32—C3353.54 (13)
C11—C12—C13—C140.6 (3)O3—C29—C32—C2652.98 (17)
C12—C13—C14—C90.6 (3)O4—C29—C32—C26177.67 (13)
C10—C9—C14—C131.8 (3)C28—C29—C32—C2658.06 (13)
C8—C9—C14—C13175.80 (18)O3—C29—C32—Cl472.84 (17)
C11—N1—C15—C160.2 (2)O4—C29—C32—Cl456.52 (16)
C11—N1—C15—C21174.94 (16)C28—C29—C32—Cl4176.12 (11)
C12—N2—C16—C150.0 (2)C40—N4—C33—C340.2 (2)
C12—N2—C16—C17174.32 (17)C40—N4—C33—C32179.04 (16)
N1—C15—C16—N20.3 (3)C26—C32—C33—N4108.00 (19)
C21—C15—C16—N2176.07 (16)C29—C32—C33—N4146.04 (17)
N1—C15—C16—C17175.11 (16)Cl4—C32—C33—N419.7 (2)
C21—C15—C16—C170.63 (18)C26—C32—C33—C3471.04 (16)
N2—C16—C17—C23105.5 (2)C29—C32—C33—C3434.92 (16)
C15—C16—C17—C2369.60 (17)Cl4—C32—C33—C34161.21 (12)
N2—C16—C17—C18149.21 (18)C35—N3—C34—C330.6 (2)
C15—C16—C17—C1835.69 (17)C35—N3—C34—C28177.69 (16)
N2—C16—C17—Cl221.9 (2)N4—C33—C34—N30.6 (3)
C15—C16—C17—Cl2162.98 (12)C32—C33—C34—N3179.72 (15)
C20—O2—C18—O140.5 (4)N4—C33—C34—C28178.03 (16)
C20'—O2—C18—O1'42.4 (3)C32—C33—C34—C281.07 (17)
C20—O2—C18—C17173.7 (3)C25—C28—C34—N3109.96 (19)
C20'—O2—C18—C1776.3 (2)C29—C28—C34—N3144.81 (18)
C20—O2—C18—C2171.1 (3)Cl3—C28—C34—N316.7 (2)
C20'—O2—C18—C21178.93 (19)C25—C28—C34—C3368.59 (16)
C16—C17—C18—O261.27 (18)C29—C28—C34—C3336.64 (16)
C23—C17—C18—O2171.99 (14)Cl3—C28—C34—C33164.71 (12)
Cl2—C17—C18—O264.14 (18)C34—N3—C35—C36178.85 (16)
C16—C17—C18—O1156.6 (3)C34—N3—C35—C400.2 (2)
C23—C17—C18—O145.9 (3)N3—C35—C36—C37178.06 (17)
Cl2—C17—C18—O178.0 (3)C40—C35—C36—C370.6 (3)
C16—C17—C18—O1'174.69 (17)C35—C36—C37—C380.7 (3)
C23—C17—C18—O1'63.97 (19)C36—C37—C38—C390.2 (3)
Cl2—C17—C18—O1'59.9 (2)C36—C37—C38—C41178.35 (19)
C16—C17—C18—C2153.06 (14)C37—C38—C39—C400.4 (3)
C23—C17—C18—C2157.66 (14)C41—C38—C39—C40179.00 (18)
Cl2—C17—C18—C21178.46 (12)C33—N4—C40—C39178.68 (16)
O2—C18—O1—C1964.7 (5)C33—N4—C40—C350.2 (2)
C17—C18—O1—C1977.9 (4)C38—C39—C40—N4178.00 (17)
C21—C18—O1—C19177.1 (4)C38—C39—C40—C350.5 (3)
O2—C18—O1'—C19'61.3 (3)N3—C35—C40—N40.2 (3)
C17—C18—O1'—C19'174.2 (2)C36—C35—C40—N4178.43 (16)
C21—C18—O1'—C19'73.4 (3)N3—C35—C40—C39178.63 (17)
N1—C15—C21—C22104.4 (2)C36—C35—C40—C390.0 (3)
C16—C15—C21—C2271.02 (17)C39—C38—C41—C4235.4 (3)
N1—C15—C21—C18149.92 (18)C37—C38—C41—C42143.1 (2)
C16—C15—C21—C1834.61 (16)C39—C38—C41—S3145.20 (17)
N1—C15—C21—Cl123.2 (2)C37—C38—C41—S336.2 (3)
C16—C15—C21—Cl1161.29 (12)C44—S3—C41—C420.73 (17)
O2—C18—C21—C1564.39 (17)C44—S3—C41—C38179.80 (17)
O1—C18—C21—C15176.1 (2)C38—C41—C42—C43179.6 (2)
O1'—C18—C21—C15159.98 (19)S3—C41—C42—C430.2 (3)
C17—C18—C21—C1552.71 (14)C41—C42—C43—C440.7 (3)
O2—C18—C21—C22175.10 (14)C42—C43—C44—C45178.0 (10)
O1—C18—C21—C2265.4 (2)C42—C43—C44—C45'179.5 (15)
O1'—C18—C21—C2249.3 (2)C42—C43—C44—S31.2 (3)
C17—C18—C21—C2258.00 (14)C41—S3—C44—C431.12 (17)
O2—C18—C21—Cl159.65 (18)C41—S3—C44—C45178.2 (9)
O1—C18—C21—Cl159.9 (3)C41—S3—C44—C45'179.6 (15)
O1'—C18—C21—Cl176.0 (2)C43—C44—C45—C46171.1 (15)
C17—C18—C21—Cl1176.76 (12)S3—C44—C45—C468 (2)
C15—C21—C22—C2454.92 (19)C43—C44—C45—S46.1 (18)
C18—C21—C22—C24160.05 (13)S3—C44—C45—S4174.7 (7)
Cl1—C21—C22—C2472.48 (16)C48—S4—C45—C461.3 (14)
C15—C21—C22—C2368.05 (16)C48—S4—C45—C44179.2 (12)
C18—C21—C22—C2337.08 (15)C44—C45—C46—C47176.6 (17)
Cl1—C21—C22—C23164.55 (11)S4—C45—C46—C476.1 (19)
C16—C17—C23—C2755.50 (18)C45—C46—C47—C489 (2)
C18—C17—C23—C27160.40 (14)C46—C47—C48—S47.9 (17)
Cl2—C17—C23—C2772.81 (16)C45—S4—C48—C473.9 (13)
C16—C17—C23—C2267.97 (16)C43—C44—C45'—C46'26 (4)
C18—C17—C23—C2236.93 (15)S3—C44—C45'—C46'153 (2)
Cl2—C17—C23—C22163.73 (11)C43—C44—C45'—S4'166.4 (11)
C24—C22—C23—C270.1 (2)S3—C44—C45'—S4'14 (3)
C21—C22—C23—C27124.27 (15)C48'—S4'—C45'—C46'9.4 (19)
C24—C22—C23—C17124.23 (15)C48'—S4'—C45'—C44180 (2)
C21—C22—C23—C170.10 (16)C44—C45'—C46'—C47'178 (3)
C21—C22—C24—C25170.08 (13)S4'—C45'—C46'—C47'10 (2)
C23—C22—C24—C2553.00 (17)C45'—C46'—C47'—C48'4 (3)
C22—C24—C25—C28171.46 (13)C46'—C47'—C48'—S4'4 (2)
C22—C24—C25—C2653.27 (17)C45'—S4'—C48'—C47'7.6 (18)
C24—C25—C26—C270.65 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20C···N4i0.982.523.094 (5)117
C47—H47B···O2ii0.952.523.365 (19)148
C1S—H1SA···N1iii1.002.463.318 (15)143
C1S—H1SB···N1iii1.002.433.369 (15)157
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z.
Selected transannular metrical parameters (Å) between the quinoxaline rings top
N···NC···CCentroid-to-centroidaCentroid-to-ring planeaRing offseta
anti-BTbN1···N34.558 (5)C9···C253.444 (6)3.810 (2)3.778 (2)0.492 (7)
N2···N44.529 (5)C14···C263.451 (6)3.753 (2)0.659 (7)
anti-BBTN1···N34.620 (2)C9···C373.625 (2)3.950 (1)3.865 (1)0.354 (3)
N2···N44.573 (2)C14···C383.632 (2)3.934 (1)0.816 (2)
Notes: (a) measured between the six-membered aromatic rings (Dolomanov et al., 2009); (b) DeBlase et al. (2014).
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds