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The absolute configuration has been established of the enantio­pure anti-head-to-head cyclo­dimer of anthracene-2-car­boxy­lic acid (AC) cocrystallized with L-propinol and di­chloro­methane [systematic name: (S)-2-(hy­droxy­meth­yl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carb­oxy-5,6,11,12-tetrahydro-5,12:6,11-bis­([1,2]benzeno)­dibenzo[a,e][8]annulene-2-carboxyl­ate di­chloro­methane monosolvate], C5H12NO+·C30H19O4-·CH2Cl2. In the crystal structure, the AC dimer inter­acts with L-prolinol through a nine-membered hydrogen-bonded ring [R22(9)], while the di­chloro­methane mol­ecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113028461/sk3506sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113028461/sk3506Isup2.hkl
Contains datablock I

CCDC reference: 966795

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2010); cell refinement: RAPID-AUTO (Rigaku, 2010); data reduction: RAPID-AUTO (Rigaku, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

(S)-2-(Hydroxymethyl)pyrrolidin-1-ium 5-carboxyheptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-2,4,6,8,11 (16),12,14,17 (22),18,20,23 (28),24,26-tridecaene-13-carboxylate dichloromethane monosolvate top
Crystal data top
C5H12NO+·C30H19O4·CH2Cl2F(000) = 660.00
Mr = 630.57Dx = 1.353 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ybCell parameters from 11621 reflections
a = 11.4579 (2) Åθ = 3.2–68.2°
b = 9.83146 (18) ŵ = 2.25 mm1
c = 13.8027 (3) ÅT = 123 K
β = 95.6581 (10)°Platelet, colourless
V = 1547.26 (5) Å30.80 × 0.20 × 0.10 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4490 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.067
ω scansθmax = 68.2°
Absorption correction: part of the refinement model (ΔF)
(Walker & Stuart, 1983)
h = 1313
Tmin = 0.654, Tmax = 0.798k = 1111
17245 measured reflectionsl = 1615
5117 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0586P)2 + 0.8448P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
5117 reflectionsΔρmax = 0.27 e Å3
413 parametersΔρmin = 0.41 e Å3
1 restraintAbsolute structure: Flack (1983), with 2125 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (2)
Secondary atom site location: difference Fourier map
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.38528 (10)0.53288 (15)0.42094 (8)0.0555 (4)
Cl20.38727 (10)0.70849 (13)0.59280 (8)0.0498 (3)
O10.0495 (2)0.4902 (3)0.32584 (15)0.0272 (6)
O20.1128 (3)0.3644 (3)0.31536 (17)0.0306 (6)
O30.1828 (3)0.2102 (3)0.37657 (16)0.0321 (6)
O40.1568 (3)0.3293 (3)0.23795 (17)0.0275 (6)
O50.0631 (3)0.4727 (4)0.52146 (19)0.0403 (8)
N10.1817 (3)0.4939 (4)0.4732 (3)0.0271 (7)
C10.0166 (3)0.3973 (4)0.2857 (3)0.0236 (8)
C20.0226 (3)0.3242 (4)0.1990 (3)0.0235 (8)
C30.1306 (3)0.3533 (4)0.1641 (3)0.0227 (8)
C40.1642 (3)0.2875 (4)0.0815 (3)0.0227 (8)
C50.2781 (3)0.3211 (4)0.0384 (3)0.0221 (8)
C60.2482 (3)0.3403 (4)0.0701 (3)0.0241 (8)
C70.2921 (4)0.4484 (4)0.1206 (3)0.0276 (8)
C80.2607 (4)0.4605 (5)0.2208 (3)0.0326 (9)
C90.1867 (4)0.3664 (5)0.2687 (3)0.0331 (9)
C100.1436 (3)0.2571 (5)0.2189 (3)0.0286 (9)
C110.1736 (3)0.2445 (4)0.1188 (3)0.0223 (8)
C120.1288 (3)0.1298 (4)0.0587 (3)0.0232 (8)
C130.0887 (3)0.1915 (4)0.0328 (3)0.0212 (7)
C140.0175 (3)0.1608 (4)0.0687 (3)0.0258 (8)
C150.0498 (3)0.2259 (4)0.1514 (3)0.0239 (8)
C160.3764 (3)0.2049 (4)0.0596 (3)0.0230 (8)
C170.4136 (3)0.1407 (4)0.0327 (3)0.0242 (8)
C180.5172 (3)0.1742 (5)0.0717 (3)0.0290 (9)
C190.5465 (3)0.1077 (5)0.1549 (3)0.0311 (9)
C200.4735 (3)0.0080 (5)0.1985 (3)0.0306 (9)
C210.3689 (3)0.0247 (4)0.1610 (3)0.0285 (9)
C220.3386 (3)0.0427 (4)0.0779 (3)0.0234 (8)
C230.2247 (3)0.0140 (4)0.0331 (2)0.0218 (7)
C240.2563 (3)0.0025 (4)0.0761 (3)0.0216 (8)
C250.2111 (3)0.1057 (4)0.1292 (3)0.0229 (8)
C260.2430 (3)0.1141 (4)0.2300 (3)0.0228 (8)
C270.3226 (3)0.0213 (4)0.2752 (3)0.0264 (8)
C280.3681 (3)0.0807 (4)0.2213 (3)0.0261 (8)
C290.3342 (3)0.0923 (4)0.1218 (3)0.0226 (8)
C300.1919 (3)0.2218 (4)0.2890 (3)0.0250 (8)
C310.3220 (6)0.5753 (7)0.5259 (4)0.0719 (18)
C320.1955 (4)0.7025 (5)0.5548 (3)0.0379 (9)
C330.3099 (4)0.6868 (5)0.4895 (4)0.0428 (11)
C340.3038 (4)0.5455 (5)0.4447 (3)0.0369 (10)
C350.1099 (4)0.6161 (4)0.5055 (3)0.0286 (8)
C360.0007 (4)0.5733 (5)0.5676 (3)0.0359 (10)
H1NA0.182 (4)0.431 (5)0.529 (4)0.053 (14)*
H1NB0.149 (4)0.449 (5)0.414 (4)0.049 (13)*
H30.18150.41830.19680.0272*
H50.30950.40870.06710.0265*
H5O0.066 (5)0.501 (7)0.464 (4)0.076 (19)*
H70.34270.51340.08740.0331*
H80.29050.53370.25590.0391*
H90.16490.37630.33660.0398*
H100.09410.19150.25280.0343*
H120.05940.08760.09690.0278*
H140.06820.09500.03650.0310*
H150.12200.20320.17570.0287*
H160.44710.24740.09580.0275*
H180.56760.24200.04170.0348*
H190.61700.13060.18190.0373*
H200.49520.03830.25450.0368*
H210.31850.09220.19140.0342*
H230.19220.07430.05960.0261*
H250.15880.17060.09770.0275*
H270.34550.02810.34310.0317*
H280.42280.14340.25220.0314*
H31A0.23870.59880.50750.0863*
H31B0.32340.49390.56820.0863*
H32A0.17000.79880.55840.0455*
H32B0.20380.66910.62140.0455*
H33A0.31660.75750.43820.0514*
H33B0.37810.69410.52800.0514*
H34A0.36250.48440.47000.0442*
H34B0.31950.55040.37300.0442*
H350.08700.66530.44690.0344*
H36A0.05000.65380.58190.0430*
H36B0.02270.53720.63020.0430*
H4O0.129 (5)0.385 (5)0.274 (4)0.051 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0492 (6)0.0680 (9)0.0505 (7)0.0079 (6)0.0107 (5)0.0041 (6)
Cl20.0527 (6)0.0477 (7)0.0473 (6)0.0038 (6)0.0028 (5)0.0032 (6)
O10.0375 (14)0.0261 (15)0.0182 (11)0.0059 (12)0.0040 (10)0.0001 (11)
O20.0326 (14)0.0301 (16)0.0309 (13)0.0047 (12)0.0116 (11)0.0060 (12)
O30.0519 (16)0.0267 (15)0.0187 (12)0.0004 (13)0.0081 (11)0.0007 (11)
O40.0390 (14)0.0216 (15)0.0231 (12)0.0039 (11)0.0084 (11)0.0013 (11)
O50.0475 (17)0.053 (2)0.0192 (13)0.0162 (15)0.0013 (12)0.0010 (13)
N10.0344 (16)0.0256 (18)0.0211 (14)0.0010 (14)0.0024 (12)0.0027 (13)
C10.0290 (18)0.024 (2)0.0178 (15)0.0022 (15)0.0014 (13)0.0003 (15)
C20.0302 (18)0.021 (2)0.0190 (16)0.0030 (15)0.0020 (13)0.0028 (14)
C30.0297 (18)0.0197 (19)0.0185 (16)0.0004 (15)0.0015 (13)0.0010 (14)
C40.0238 (17)0.0237 (19)0.0198 (16)0.0027 (15)0.0009 (13)0.0038 (15)
C50.0268 (17)0.0190 (19)0.0204 (16)0.0013 (14)0.0017 (13)0.0002 (14)
C60.0287 (18)0.025 (2)0.0182 (16)0.0040 (16)0.0006 (13)0.0025 (15)
C70.0287 (18)0.028 (3)0.0272 (18)0.0010 (16)0.0064 (14)0.0021 (15)
C80.044 (3)0.029 (3)0.0267 (19)0.0010 (18)0.0092 (16)0.0063 (16)
C90.044 (3)0.035 (3)0.0202 (18)0.0070 (19)0.0011 (15)0.0076 (17)
C100.0283 (18)0.038 (3)0.0192 (16)0.0041 (16)0.0002 (14)0.0022 (15)
C110.0189 (16)0.027 (2)0.0204 (16)0.0030 (14)0.0008 (12)0.0017 (14)
C120.0241 (17)0.027 (2)0.0179 (16)0.0023 (15)0.0010 (13)0.0002 (15)
C130.0217 (16)0.0226 (19)0.0184 (15)0.0012 (15)0.0021 (12)0.0007 (15)
C140.0292 (18)0.024 (2)0.0234 (16)0.0006 (16)0.0015 (14)0.0003 (15)
C150.0220 (16)0.024 (2)0.0259 (16)0.0019 (15)0.0003 (13)0.0009 (15)
C160.0208 (16)0.027 (2)0.0204 (15)0.0055 (16)0.0016 (12)0.0002 (16)
C170.0248 (18)0.026 (2)0.0219 (17)0.0002 (15)0.0007 (13)0.0039 (15)
C180.0275 (18)0.032 (3)0.0275 (17)0.0023 (17)0.0031 (14)0.0057 (17)
C190.0215 (18)0.040 (3)0.0330 (19)0.0070 (17)0.0078 (15)0.0139 (18)
C200.0352 (19)0.036 (3)0.0208 (17)0.0121 (19)0.0049 (14)0.0026 (17)
C210.0330 (19)0.031 (3)0.0207 (17)0.0057 (17)0.0006 (14)0.0029 (16)
C220.0258 (17)0.027 (2)0.0175 (15)0.0045 (16)0.0010 (13)0.0039 (15)
C230.0284 (17)0.0187 (19)0.0176 (15)0.0025 (15)0.0008 (13)0.0007 (14)
C240.0236 (16)0.023 (2)0.0174 (16)0.0007 (15)0.0002 (13)0.0013 (14)
C250.0212 (17)0.027 (2)0.0202 (16)0.0002 (15)0.0008 (13)0.0027 (15)
C260.0281 (18)0.023 (2)0.0173 (16)0.0058 (15)0.0030 (13)0.0015 (14)
C270.0289 (18)0.032 (3)0.0174 (16)0.0002 (16)0.0041 (13)0.0007 (15)
C280.0280 (18)0.027 (3)0.0224 (17)0.0025 (16)0.0038 (14)0.0011 (15)
C290.0228 (17)0.024 (2)0.0205 (16)0.0022 (15)0.0021 (13)0.0003 (15)
C300.0289 (18)0.0209 (19)0.0256 (17)0.0020 (16)0.0044 (14)0.0014 (15)
C310.089 (4)0.073 (5)0.059 (4)0.044 (4)0.033 (3)0.013 (3)
C320.042 (3)0.027 (3)0.046 (3)0.0081 (19)0.0125 (17)0.012 (2)
C330.037 (3)0.038 (3)0.054 (3)0.009 (2)0.0086 (19)0.005 (3)
C340.033 (2)0.043 (3)0.033 (2)0.0036 (19)0.0010 (16)0.0054 (19)
C350.0309 (19)0.026 (2)0.0289 (18)0.0040 (16)0.0039 (14)0.0048 (15)
C360.036 (2)0.044 (3)0.0271 (18)0.0005 (19)0.0009 (15)0.0089 (18)
Geometric parameters (Å, º) top
Cl1—C311.733 (6)C26—C271.393 (5)
Cl2—C311.730 (6)C26—C301.491 (5)
O1—C11.278 (5)C27—C281.381 (6)
O2—C11.256 (5)C28—C291.395 (5)
O3—C301.228 (4)C32—C331.524 (6)
O4—C301.311 (5)C32—C351.509 (6)
O5—C361.418 (6)C33—C341.525 (7)
N1—C341.504 (5)C35—C361.505 (6)
N1—C351.499 (5)O4—H4O0.83 (5)
C1—C21.502 (5)O5—H5O0.84 (6)
C2—C31.401 (5)N1—H1NA0.99 (5)
C2—C151.396 (5)N1—H1NB1.03 (5)
C3—C41.397 (5)C3—H30.950
C4—C51.522 (5)C5—H51.000
C4—C131.406 (5)C7—H70.950
C5—C61.515 (5)C8—H80.950
C5—C161.611 (5)C9—H90.950
C6—C71.392 (6)C10—H100.950
C6—C111.399 (5)C12—H121.000
C7—C81.399 (5)C14—H140.950
C8—C91.379 (6)C15—H150.950
C9—C101.393 (6)C16—H161.000
C10—C111.396 (5)C18—H180.950
C11—C121.518 (5)C19—H190.950
C12—C131.513 (5)C20—H200.950
C12—C231.598 (5)C21—H210.950
C13—C141.392 (5)C23—H231.000
C14—C151.390 (5)C25—H250.950
C16—C171.520 (5)C27—H270.950
C16—C291.509 (5)C28—H280.950
C17—C181.390 (5)C31—H31A0.990
C17—C221.396 (5)C31—H31B0.990
C18—C191.391 (6)C32—H32A0.990
C19—C201.387 (6)C32—H32B0.990
C20—C211.390 (6)C33—H33A0.990
C21—C221.397 (5)C33—H33B0.990
C22—C231.525 (5)C34—H34A0.990
C23—C241.523 (5)C34—H34B0.990
C24—C251.382 (5)C35—H351.000
C24—C291.397 (5)C36—H36A0.990
C25—C261.406 (5)C36—H36B0.990
O1···C32.842 (5)C6···H14ix3.3055
O2···C152.797 (5)C7···H14ix3.2539
O3···C272.901 (5)C7···H15ix3.2181
O4···C252.768 (5)C8···H15ix2.9667
O4···C273.585 (5)C8···H31Bviii3.0853
O5···N12.826 (4)C9···H31Bviii3.1281
C2···C132.808 (5)C9···H33Avi3.0857
C3···C142.785 (5)C9···H35vi3.2719
C3···C163.597 (5)C9···H36Bviii3.1407
C3···C293.554 (5)C10···H35vi3.2761
C4···C112.809 (5)C10···H4Oix3.43 (5)
C4···C152.789 (5)C13···H25ix3.4807
C4···C233.229 (5)C14···H23ix3.2794
C4···C243.044 (6)C14···H25ix3.1481
C4···C283.525 (5)C15···H23ix2.7776
C4···C292.752 (5)C15···H36Biv3.5678
C5···C122.794 (5)C17···H7xiv3.3463
C5···C183.566 (5)C18···H5xiv3.2767
C5···C223.282 (5)C18···H7xiv3.0331
C5···C233.216 (5)C19···H5xiv2.7606
C5···C243.237 (6)C19···H7xiv3.5793
C5···C283.536 (5)C20···H5xiv3.0879
C6···C92.774 (5)C20···H16xiv3.0246
C6···C132.830 (5)C20···H34Bvi2.8726
C6···C172.741 (5)C21···H16xiv3.1468
C6···C183.490 (5)C21···H34Bvi3.0177
C6···C223.109 (6)C22···H18xiv3.5029
C6···C233.264 (6)C24···H18xiv3.2851
C7···C102.796 (6)C25···H18xiv3.2759
C7···C163.519 (5)C25···H19xiv3.2929
C7···C173.497 (6)C26···H1NAiv3.50 (5)
C8···C112.786 (6)C26···H19xiv3.0851
C10···C223.516 (5)C26···H32Biv3.5133
C10···C233.562 (5)C27···H1NAiv3.32 (5)
C11···C163.239 (5)C27···H32Biv2.7882
C11···C173.061 (5)C27···H33Biv3.4533
C11···C213.551 (6)C27···H34Aiv3.5014
C11···C222.760 (5)C28···H32Biv3.1328
C12···C163.217 (5)C30···H1NAiv2.94 (5)
C12···C173.249 (5)C30···H10vi3.3751
C12···C213.554 (6)C30···H19xiv3.1181
C12···C253.535 (5)C30···H31Av3.4888
C12···C293.275 (5)C30···H36Biv3.4508
C13···C163.283 (5)C31···H5O3.06 (6)
C13···C242.732 (5)C31···H8vii3.0960
C13···C253.451 (6)C31···H9vii3.3682
C13···C293.114 (5)C31···H32Aiv3.3729
C14···C233.539 (5)C31···H33Aiv3.1646
C14···C243.517 (5)C31···H36A3.3737
C16···C232.782 (5)C32···H5Oiii3.31 (7)
C17···C202.779 (5)C32···H9ix3.5104
C17···C242.831 (5)C32···H27iii3.2504
C18···C212.796 (6)C32···H31Biii3.5708
C19···C222.777 (5)C33···H9ix3.3732
C22···C292.805 (5)C33···H27iii3.1872
C24···C272.784 (5)C33···H31Biii3.1229
C25···C282.786 (5)C34···H20ix3.3536
C26···C292.784 (5)C34···H27iii3.0994
Cl1···O3i3.444 (3)C35···H9ix3.4768
Cl1···C34ii3.547 (4)C35···H10ix3.5884
Cl2···C34iii3.473 (5)C36···H9vii2.9342
O1···O3i3.360 (4)C36···H31A2.9538
O1···O4i2.534 (4)H1NA···Cl2iv3.52 (5)
O1···O52.695 (4)H1NA···O23.19 (5)
O1···N13.495 (4)H1NA···O3iii1.90 (5)
O1···C30i3.331 (5)H1NA···C26iii3.50 (5)
O1···C353.451 (5)H1NA···C27iii3.32 (5)
O1···C363.537 (5)H1NA···C30iii2.94 (5)
O2···O53.487 (4)H1NA···H27iii2.7322
O2···N12.708 (4)H1NA···H31Aiv3.3570
O2···C343.453 (5)H1NA···H36Aiv3.5340
O2···C36iv3.475 (5)H1NB···O12.72 (5)
O3···Cl1v3.444 (3)H1NB···O21.68 (5)
O3···O1v3.360 (4)H1NB···O3iii3.35 (5)
O3···N1iv2.886 (4)H1NB···C12.50 (5)
O3···C31v3.254 (7)H1NB···H10ix3.3600
O4···O1v2.534 (4)H1NB···H21ix3.4882
O4···C1v3.444 (5)H1NB···H36Aiv3.1199
O4···C3v3.288 (5)H3···O4i2.5668
O4···C10vi3.529 (5)H3···H12ix3.3969
O5···O12.695 (4)H3···H19xi3.1337
O5···O23.487 (4)H3···H32Aiv3.5922
O5···C13.375 (4)H3···H32Biv3.4980
O5···C9vii3.267 (5)H3···H4Oi2.3162
O5···C313.127 (7)H5···C18xi3.2767
O5···C32iv3.283 (6)H5···C19xi2.7606
O5···C35iv3.571 (6)H5···C20xi3.0879
N1···O13.495 (4)H5···H14ix3.5017
N1···O22.708 (4)H5···H18xi3.5978
N1···O3iii2.886 (4)H5···H19xi2.7784
N1···C13.485 (5)H5···H20xi3.2907
C1···O4i3.444 (5)H5O···O11.90 (6)
C1···O53.375 (4)H5O···O23.06 (6)
C1···N13.485 (5)H5O···O3i3.41 (7)
C3···O4i3.288 (5)H5O···C12.75 (6)
C9···O5viii3.267 (5)H5O···C313.06 (6)
C9···C36viii3.592 (6)H5O···C32iv3.31 (7)
C10···O4ix3.529 (5)H5O···H9vii3.1190
C30···O1v3.331 (5)H5O···H31A2.2278
C31···O3i3.254 (7)H5O···H31B3.1498
C31···O53.127 (7)H5O···H32Aiv2.3505
C32···O5iii3.283 (6)H5O···H35iv3.5182
C34···Cl1x3.547 (4)H5O···H4Oi3.00 (8)
C34···Cl2iv3.473 (5)H7···C17xi3.3463
C34···O23.453 (5)H7···C18xi3.0331
C35···O13.451 (5)H7···C19xi3.5793
C35···O5iii3.571 (6)H7···H14ix3.3861
C36···O13.537 (5)H7···H15ix3.2799
C36···O2iii3.475 (5)H7···H16xi3.3407
C36···C9vii3.592 (6)H7···H18xi2.9868
O1···H32.5477H8···Cl2viii2.9999
O2···H152.4892H8···C31viii3.0960
O3···H272.6577H8···H15ix2.8546
O3···H4O2.27 (5)H8···H28xi3.4533
O4···H252.4883H8···H31Aviii3.3229
O5···H1NA2.85 (5)H8···H31Bviii2.5238
O5···H1NB2.74 (5)H8···H36Aviii3.5754
O5···H352.6941H9···O5viii2.3764
N1···H5O2.86 (6)H9···C31viii3.3682
N1···H32A3.2175H9···C32vi3.5104
N1···H32B2.7052H9···C33vi3.3732
N1···H33A3.0323H9···C35vi3.4768
N1···H33B3.1377H9···C36viii2.9342
N1···H36A3.3142H9···H5Oviii3.1190
N1···H36B2.7232H9···H31Aviii3.2388
C1···H32.6925H9···H31Bviii2.6142
C1···H152.6538H9···H32Avi3.1611
C2···H143.2766H9···H33Avi2.6145
C3···H52.6132H9···H35vi2.6738
C3···H153.2669H9···H36Aviii3.1860
C4···H123.2837H9···H36Bviii2.6721
C4···H143.2762H10···O1vi2.7044
C4···H163.2516H10···O2vi3.3431
C5···H32.7198H10···O3ix3.5853
C5···H72.7190H10···O4ix2.9092
C6···H83.2667H10···C1vi3.0464
C6···H103.2765H10···C30ix3.3751
C6···H123.2917H10···C35vi3.5884
C6···H163.2000H10···H1NBvi3.3600
C7···H52.6082H10···H34Bvi3.4914
C7···H93.2642H10···H35vi2.6845
C8···H103.2654H10···H4Oix2.6488
C9···H73.2659H12···O1vi3.4175
C10···H83.2652H12···O4ix3.1047
C10···H122.6198H12···C1vi3.2053
C11···H53.2905H12···C2vi3.0513
C11···H73.2813H12···C3vi3.2415
C11···H93.2655H12···H3vi3.3969
C11···H233.2411H12···H25ix3.4493
C12···H102.7365H12···H4Oix3.1065
C12···H142.7435H14···C4vi3.5563
C13···H33.2801H14···C6vi3.3055
C13···H53.3086H14···C7vi3.2539
C13···H153.2673H14···H5vi3.5017
C13···H233.1882H14···H7vi3.3861
C14···H122.6293H14···H23ix3.5750
C15···H33.2665H14···H25ix3.0731
C16···H182.7373H15···C7vi3.2181
C16···H282.7267H15···C8vi2.9667
C17···H53.2536H15···H7vi3.2799
C17···H193.2608H15···H8vi2.8546
C17···H213.2796H15···H21ix3.0430
C17···H233.2944H15···H23ix2.7828
C18···H162.6214H15···H36Aiv3.4003
C18···H203.2661H15···H36Biv3.4225
C19···H213.2681H16···C20xi3.0246
C20···H183.2684H16···C21xi3.1468
C21···H193.2652H16···H7xiv3.3407
C21···H232.6171H16···H20xi3.0645
C22···H123.2143H16···H21xi3.2779
C22···H163.2797H18···C22xi3.5029
C22···H183.2736H18···C24xi3.2851
C22···H203.2639H18···C25xi3.2759
C23···H212.7360H18···H5xiv3.5978
C23···H252.7182H18···H7xiv2.9868
C24···H123.2429H18···H23xi3.4684
C24···H163.2818H18···H25xi3.4120
C24···H283.2701H19···Cl1xiv3.4339
C25···H232.6119H19···O4xi2.8048
C25···H273.2825H19···C25xi3.2929
C25···H4O3.58 (5)H19···C26xi3.0851
C26···H283.2597H19···C30xi3.1181
C26···H4O3.06 (5)H19···H3xiv3.1337
C27···H253.2819H19···H5xiv2.7784
C28···H162.6104H19···H25xi3.3434
C29···H53.2069H19···H4Oxi3.2976
C29···H233.2858H20···Cl1xiv2.8749
C29···H253.2703H20···Cl2xv3.4142
C29···H273.2662H20···C34vi3.3536
C30···H252.6785H20···H5xiv3.2907
C30···H272.6504H20···H16xiv3.0645
C32···H1NA2.70 (5)H20···H28xiv3.2666
C32···H1NB3.23 (5)H20···H34Avi3.2127
C32···H34A3.0309H20···H34Bvi2.6154
C32···H34B3.1381H21···O2vi2.8052
C32···H36A2.8407H21···C1vi3.5748
C32···H36B2.6900H21···H1NBvi3.4882
C33···H1NA2.94 (5)H21···H15vi3.0430
C33···H1NB3.21 (5)H21···H16xiv3.2779
C33···H352.6848H21···H34Bvi2.8729
C34···H32A3.2461H23···C1vi3.5524
C34···H32B2.8608H23···C2vi3.1339
C34···H352.7470H23···C14vi3.2794
C35···H5O2.43 (6)H23···C15vi2.7776
C35···H33A2.8235H23···H14vi3.5750
C35···H33B3.2115H23···H15vi2.7828
C35···H34A3.1644H23···H18xiv3.4684
C35···H34B2.9433H25···C13vi3.4807
C36···H1NA2.51 (5)H25···C14vi3.1481
C36···H1NB2.86 (5)H25···H12vi3.4493
C36···H32A2.9394H25···H14vi3.0731
C36···H32B2.6824H25···H18xiv3.4120
H1NA···H5O3.14 (8)H25···H19xiv3.3434
H1NA···H32B2.6919H27···N1iv3.3075
H1NA···H33B3.4301H27···C32iv3.2504
H1NA···H34A2.2146H27···C33iv3.1872
H1NA···H34B2.8008H27···C34iv3.0994
H1NA···H352.8319H27···H1NAiv2.7322
H1NA···H36A3.4638H27···H32Biv2.6064
H1NA···H36B2.4201H27···H33Biv2.8194
H1NB···H5O2.55 (7)H27···H34Aiv2.5708
H1NB···H34A2.6556H28···Cl2xvi2.9670
H1NB···H34B2.2095H28···H8xiv3.4533
H1NB···H352.2727H28···H20xi3.2666
H1NB···H36B3.3047H28···H32Biv3.2035
H3···H52.4255H28···H33Biv3.1650
H5···H72.4315H31A···O13.3253
H5···H162.2436H31A···O3i2.6412
H5O···H352.3823H31A···O52.3870
H5O···H36A2.2366H31A···C30i3.4888
H5O···H36B2.6231H31A···C362.9538
H7···H82.3525H31A···H1NAiii3.3570
H8···H92.3214H31A···H5O2.2278
H9···H102.3410H31A···H8vii3.3229
H10···H122.4497H31A···H9vii3.2388
H12···H142.4625H31A···H32Aiv3.1636
H12···H232.2275H31A···H33Aiv3.5332
H14···H152.3321H31A···H36A2.5417
H16···H182.4550H31A···H4Oi3.3463
H16···H282.4293H31B···O52.9961
H18···H192.3414H31B···C8vii3.0853
H19···H202.3312H31B···C9vii3.1281
H20···H212.3415H31B···C32iv3.5708
H21···H232.4397H31B···C33iv3.1229
H23···H252.4338H31B···H5O3.1498
H25···H4O3.2658H31B···H8vii2.5238
H27···H282.3280H31B···H9vii2.6142
H32A···H33A2.2778H31B···H32Aiv3.0366
H32A···H33B2.5925H31B···H33Aiv2.3268
H32A···H352.2982H31B···H33Biv3.3178
H32A···H36A2.8855H31B···H36A3.5271
H32A···H36B3.1802H32A···Cl1iii3.4065
H32B···H33A2.8591H32A···O1iii2.7513
H32B···H33B2.2802H32A···O2iii3.5831
H32B···H34A3.1963H32A···O5iii2.4294
H32B···H352.8695H32A···C1iii3.0394
H32B···H36A3.0149H32A···C31iii3.3729
H32B···H36B2.4400H32A···H3iii3.5922
H33A···H34A2.7790H32A···H5Oiii2.3505
H33A···H34B2.2253H32A···H9ix3.1611
H33A···H352.7742H32A···H31Aiii3.1636
H33B···H34A2.2250H32A···H31Biii3.0366
H33B···H34B2.7035H32B···C1iii3.5247
H34B···H352.9790H32B···C2iii3.4303
H35···H36A2.3183H32B···C3iii3.5015
H35···H36B2.8578H32B···C26iii3.5133
Cl1···H19xi3.4339H32B···C27iii2.7882
Cl1···H20xi2.8749H32B···C28iii3.1328
Cl1···H32Aiv3.4065H32B···H3iii3.4980
Cl1···H33Aiv3.4679H32B···H27iii2.6064
Cl1···H33Bii3.3557H32B···H28iii3.2035
Cl1···H33Biv3.4067H33A···Cl1iii3.4679
Cl1···H34Aii2.9414H33A···O5iii3.5918
Cl1···H34Bii3.5147H33A···C9ix3.0857
Cl1···H4Oi3.50 (5)H33A···C31iii3.1646
Cl2···H1NAiii3.52 (5)H33A···H9ix2.6145
Cl2···H8vii2.9999H33A···H31Aiii3.5332
Cl2···H20xii3.4142H33A···H31Biii2.3268
Cl2···H28xiii2.9670H33B···Cl1x3.3557
Cl2···H33Bii2.9194H33B···Cl1iii3.4067
Cl2···H34Aiii2.8540H33B···Cl2x2.9194
Cl2···H34Biii3.4928H33B···C27iii3.4533
O1···H1NB2.72 (5)H33B···H27iii2.8194
O1···H5O1.90 (6)H33B···H28iii3.1650
O1···H10ix2.7044H33B···H31Biii3.3178
O1···H12ix3.4175H34A···Cl1x2.9414
O1···H31A3.3253H34A···Cl2iv2.8540
O1···H32Aiv2.7513H34A···O3iii3.3944
O1···H352.9519H34A···C27iii3.5014
O1···H4Oi1.72 (5)H34A···H20ix3.2127
O2···H1NA3.19 (5)H34A···H27iii2.5708
O2···H1NB1.68 (5)H34B···Cl1x3.5147
O2···H5O3.06 (6)H34B···Cl2iv3.4928
O2···H10ix3.3431H34B···O23.1555
O2···H21ix2.8052H34B···C20ix2.8726
O2···H32Aiv3.5831H34B···C21ix3.0177
O2···H34B3.1555H34B···H10ix3.4914
O2···H353.4687H34B···H20ix2.6154
O2···H36Aiv2.5715H34B···H21ix2.8729
O3···H1NAiv1.90 (5)H35···O12.9519
O3···H1NBiv3.35 (5)H35···O23.4687
O3···H5Ov3.41 (7)H35···O3i3.5482
O3···H10vi3.5853H35···O5iii3.0615
O3···H31Av2.6412H35···C13.5911
O3···H34Aiv3.3944H35···C9ix3.2719
O3···H35v3.5482H35···C10ix3.2761
O3···H36Biv3.0418H35···H5Oiii3.5182
O4···H3v2.5668H35···H9ix2.6738
O4···H10vi2.9092H35···H10ix2.6845
O4···H12vi3.1047H36A···O2iii2.5715
O4···H19xiv2.8048H36A···C1iii3.0591
O5···H9vii2.3764H36A···C313.3737
O5···H31A2.3870H36A···H1NAiii3.5340
O5···H31B2.9961H36A···H1NBiii3.1199
O5···H32Aiv2.4294H36A···H8vii3.5754
O5···H33Aiv3.5918H36A···H9vii3.1860
O5···H35iv3.0615H36A···H15iii3.4003
N1···H27iii3.3075H36A···H31A2.5417
C1···H1NB2.50 (5)H36A···H31B3.5271
C1···H5O2.75 (6)H36B···O3iii3.0418
C1···H10ix3.0464H36B···C9vii3.1407
C1···H12ix3.2053H36B···C15iii3.5678
C1···H21ix3.5748H36B···C30iii3.4508
C1···H23ix3.5524H36B···H9vii2.6721
C1···H32Aiv3.0394H36B···H15iii3.4225
C1···H32Biv3.5247H4O···Cl1v3.50 (5)
C1···H353.5911H4O···O1v1.72 (5)
C1···H36Aiv3.0591H4O···C1v2.72 (5)
C1···H4Oi2.72 (5)H4O···C2v3.23 (5)
C2···H12ix3.0513H4O···C3v2.99 (5)
C2···H23ix3.1339H4O···C10vi3.43 (5)
C2···H32Biv3.4303H4O···H3v2.3162
C2···H4Oi3.23 (5)H4O···H5Ov3.00 (8)
C3···H12ix3.2415H4O···H10vi2.6488
C3···H32Biv3.5015H4O···H12vi3.1065
C3···H4Oi2.99 (5)H4O···H19xiv3.2976
C4···H14ix3.5563H4O···H31Av3.3463
C34—N1—C35106.0 (3)C34—N1—H1NA110 (3)
O1—C1—O2123.0 (4)C34—N1—H1NB109 (3)
O1—C1—C2118.4 (3)C35—N1—H1NA108 (3)
O2—C1—C2118.5 (3)C35—N1—H1NB110 (3)
C1—C2—C3121.4 (3)H1NA—N1—H1NB112 (4)
C1—C2—C15119.7 (3)C2—C3—H3119.648
C3—C2—C15118.9 (3)C4—C3—H3119.658
C2—C3—C4120.7 (4)C4—C5—H5108.730
C3—C4—C5122.2 (3)C6—C5—H5108.732
C3—C4—C13119.7 (3)C16—C5—H5108.739
C5—C4—C13118.0 (3)C6—C7—H7120.356
C4—C5—C6107.1 (3)C8—C7—H7120.348
C4—C5—C16112.7 (3)C7—C8—H8119.891
C6—C5—C16110.7 (3)C9—C8—H8119.879
C5—C6—C7122.2 (3)C8—C9—H9119.603
C5—C6—C11117.3 (3)C10—C9—H9119.608
C7—C6—C11120.5 (3)C9—C10—H10120.248
C6—C7—C8119.3 (4)C11—C10—H10120.254
C7—C8—C9120.2 (4)C11—C12—H12108.348
C8—C9—C10120.8 (4)C13—C12—H12108.351
C9—C10—C11119.5 (4)C23—C12—H12108.344
C6—C11—C10119.7 (4)C13—C14—H14119.829
C6—C11—C12117.5 (3)C15—C14—H14119.829
C10—C11—C12122.9 (3)C2—C15—H15119.616
C11—C12—C13107.8 (3)C14—C15—H15119.603
C11—C12—C23112.9 (3)C5—C16—H16108.166
C13—C12—C23111.1 (3)C17—C16—H16108.165
C4—C13—C12116.4 (3)C29—C16—H16108.175
C4—C13—C14119.6 (3)C17—C18—H18120.229
C12—C13—C14124.0 (3)C19—C18—H18120.226
C13—C14—C15120.3 (4)C18—C19—H19119.789
C2—C15—C14120.8 (4)C20—C19—H19119.798
C5—C16—C17113.0 (3)C19—C20—H20119.791
C5—C16—C29111.5 (3)C21—C20—H20119.780
C17—C16—C29107.7 (3)C20—C21—H21120.330
C16—C17—C18123.1 (4)C22—C21—H21120.334
C16—C17—C22116.8 (3)C12—C23—H23108.323
C18—C17—C22120.1 (4)C22—C23—H23108.315
C17—C18—C19119.5 (4)C24—C23—H23108.316
C18—C19—C20120.4 (4)C24—C25—H25120.211
C19—C20—C21120.4 (4)C26—C25—H25120.222
C20—C21—C22119.3 (4)C26—C27—H27120.007
C17—C22—C21120.1 (4)C28—C27—H27120.005
C17—C22—C23117.4 (3)C27—C28—H28119.791
C21—C22—C23122.5 (3)C29—C28—H28119.789
C12—C23—C22112.0 (3)Cl1—C31—H31A108.352
C12—C23—C24112.7 (3)Cl1—C31—H31B108.353
C22—C23—C24107.0 (3)Cl2—C31—H31A108.356
C23—C24—C25122.5 (3)Cl2—C31—H31B108.356
C23—C24—C29117.0 (3)H31A—C31—H31B107.436
C25—C24—C29120.4 (3)C33—C32—H32A111.026
C24—C25—C26119.6 (4)C33—C32—H32B111.030
C25—C26—C27119.9 (4)C35—C32—H32A111.033
C25—C26—C30120.3 (3)C35—C32—H32B111.030
C27—C26—C30119.7 (3)H32A—C32—H32B109.020
C26—C27—C28120.0 (3)C32—C33—H33A110.712
C27—C28—C29120.4 (4)C32—C33—H33B110.717
C16—C29—C24117.3 (3)C34—C33—H33A110.715
C16—C29—C28123.1 (3)C34—C33—H33B110.718
C24—C29—C28119.6 (4)H33A—C33—H33B108.814
O3—C30—O4123.6 (4)N1—C34—H34A110.479
O3—C30—C26123.2 (4)N1—C34—H34B110.481
O4—C30—C26113.2 (3)C33—C34—H34A110.484
Cl1—C31—Cl2115.7 (4)C33—C34—H34B110.481
C33—C32—C35103.6 (4)H34A—C34—H34B108.668
C32—C33—C34105.1 (4)N1—C35—H35109.079
N1—C34—C33106.2 (3)C32—C35—H35109.070
N1—C35—C32102.9 (3)C36—C35—H35109.073
N1—C35—C36110.2 (4)O5—C36—H36A109.187
C32—C35—C36116.2 (4)O5—C36—H36B109.185
O5—C36—C35112.1 (3)C35—C36—H36A109.183
C30—O4—H4O109 (4)C35—C36—H36B109.189
C36—O5—H5O105 (5)H36A—C36—H36B107.891
C34—N1—C35—C3235.5 (4)C12—C13—C14—C15177.6 (3)
C34—N1—C35—C36160.0 (3)C13—C14—C15—C20.9 (5)
C35—N1—C34—C3316.9 (4)C5—C16—C17—C18101.7 (4)
O1—C1—C2—C31.9 (5)C5—C16—C17—C2279.0 (4)
O1—C1—C2—C15177.6 (3)C5—C16—C29—C2477.4 (4)
O2—C1—C2—C3178.0 (3)C5—C16—C29—C28101.7 (4)
O2—C1—C2—C152.5 (5)C17—C16—C29—C2447.1 (4)
C1—C2—C3—C4177.9 (3)C17—C16—C29—C28133.8 (3)
C1—C2—C15—C14177.4 (3)C29—C16—C17—C18134.7 (3)
C3—C2—C15—C142.1 (5)C29—C16—C17—C2244.5 (4)
C15—C2—C3—C41.6 (5)C16—C17—C18—C19178.0 (3)
C2—C3—C4—C5177.0 (3)C16—C17—C22—C21177.5 (3)
C2—C3—C4—C130.2 (5)C16—C17—C22—C232.5 (5)
C3—C4—C5—C6131.7 (3)C18—C17—C22—C211.7 (5)
C3—C4—C5—C16106.2 (4)C18—C17—C22—C23178.2 (3)
C3—C4—C13—C12177.1 (3)C22—C17—C18—C191.2 (5)
C3—C4—C13—C141.5 (5)C17—C18—C19—C200.4 (6)
C5—C4—C13—C120.2 (5)C18—C19—C20—C211.4 (6)
C5—C4—C13—C14178.4 (3)C19—C20—C21—C220.8 (6)
C13—C4—C5—C645.1 (4)C20—C21—C22—C170.8 (5)
C13—C4—C5—C1676.9 (4)C20—C21—C22—C23179.2 (3)
C4—C5—C6—C7134.8 (3)C17—C22—C23—C1277.0 (4)
C4—C5—C6—C1145.0 (4)C17—C22—C23—C2447.0 (4)
C4—C5—C16—C17118.7 (3)C21—C22—C23—C12103.0 (4)
C4—C5—C16—C292.7 (4)C21—C22—C23—C24133.0 (3)
C6—C5—C16—C171.2 (4)C12—C23—C24—C25100.9 (4)
C6—C5—C16—C29122.7 (3)C12—C23—C24—C2979.0 (4)
C16—C5—C6—C7101.9 (4)C22—C23—C24—C25135.5 (3)
C16—C5—C6—C1178.3 (4)C22—C23—C24—C2944.6 (4)
C5—C6—C7—C8179.8 (3)C23—C24—C25—C26179.3 (3)
C5—C6—C11—C10179.7 (3)C23—C24—C29—C162.1 (5)
C5—C6—C11—C120.1 (5)C23—C24—C29—C28178.8 (3)
C7—C6—C11—C100.5 (5)C25—C24—C29—C16177.9 (3)
C7—C6—C11—C12179.7 (3)C25—C24—C29—C281.3 (5)
C11—C6—C7—C80.0 (6)C29—C24—C25—C260.7 (5)
C6—C7—C8—C90.3 (6)C24—C25—C26—C272.0 (5)
C7—C8—C9—C101.0 (6)C24—C25—C26—C30177.9 (3)
C8—C9—C10—C111.5 (6)C25—C26—C27—C281.4 (5)
C9—C10—C11—C61.2 (6)C25—C26—C30—O3154.7 (4)
C9—C10—C11—C12179.0 (3)C25—C26—C30—O424.8 (5)
C6—C11—C12—C1345.7 (4)C27—C26—C30—O325.2 (5)
C6—C11—C12—C2377.3 (4)C27—C26—C30—O4155.4 (3)
C10—C11—C12—C13134.4 (4)C30—C26—C27—C28178.4 (3)
C10—C11—C12—C23102.6 (4)C26—C27—C28—C290.5 (6)
C11—C12—C13—C445.5 (4)C27—C28—C29—C16177.2 (3)
C11—C12—C13—C14133.1 (3)C27—C28—C29—C241.8 (6)
C11—C12—C23—C222.0 (4)C33—C32—C35—N140.1 (4)
C11—C12—C23—C24118.8 (3)C33—C32—C35—C36160.6 (3)
C13—C12—C23—C22123.1 (3)C35—C32—C33—C3429.7 (4)
C13—C12—C23—C242.4 (4)C32—C33—C34—N18.0 (4)
C23—C12—C13—C478.6 (4)N1—C35—C36—O552.4 (4)
C23—C12—C13—C14102.8 (4)C32—C35—C36—O5168.9 (4)
C4—C13—C14—C151.0 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y+1/2, z+1; (iv) x, y1/2, z+1; (v) x, y1, z; (vi) x, y1/2, z; (vii) x, y, z+1; (viii) x, y, z1; (ix) x, y+1/2, z; (x) x1, y, z; (xi) x+1, y+1/2, z; (xii) x, y+1, z+1; (xiii) x+1, y+1/2, z+1; (xiv) x+1, y1/2, z; (xv) x, y1, z1; (xvi) x+1, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O1v0.83 (5)1.72 (5)2.534 (4)167 (5)
O5—H5O···O10.84 (6)1.90 (6)2.695 (4)156 (7)
N1—H1NA···O3iii0.99 (5)1.90 (5)2.886 (4)172 (5)
N1—H1NB···O21.03 (5)1.68 (5)2.708 (4)173 (4)
Symmetry codes: (iii) x, y+1/2, z+1; (v) x, y1, z.
 

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