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The crystal structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide have been determined.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001778/hb7962sup1.cif
Contains datablocks 3a, 3b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001778/hb79623asup2.hkl
Contains datablock 3a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001778/hb79623bsup3.hkl
Contains datablock 3b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001778/hb79623asup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001778/hb79623bsup5.cml
Supplementary material

CCDC references: 2025600; 2025601

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.040
  • wR factor = 0.111
  • Data-to-parameter ratio = 23.6

checkCIF/PLATON results

No syntax errors found



Datablock: 3a


Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A ..CL1 . 2.86 Ang.
Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 26 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 13 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: 3b
Alert level C PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.4 Ratio PLAT220_ALERT_2_C NonSolvent Resd 2 C Ueq(max)/Ueq(min) Range 3.7 Ratio PLAT222_ALERT_3_C NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 5.3 Ratio PLAT222_ALERT_3_C NonSolvent Resd 2 H Uiso(max)/Uiso(min) Range 4.2 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C16A --C19A . 5.5 s.u. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.5 Note PLAT480_ALERT_4_C Long H...A H-Bond Reported H8AB ..CL1A . 2.92 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A ..O5C . 2.63 Ang.
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 20 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 20 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 1 Report PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 1 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 38% Note PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 21 Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 399 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 35 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 17 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 8 ALERT level C = Check. Ensure it is not caused by an omission or oversight 11 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: APEX2 (Bruker, 2010); cell refinement: APEX2 (Bruker, 2010); data reduction: APEX2 and SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-Chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide (3a) top
Crystal data top
C17H20ClNO5F(000) = 744
Mr = 353.79Dx = 1.413 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.654 (3) ÅCell parameters from 5173 reflections
b = 8.9148 (17) Åθ = 2.7–31.0°
c = 13.045 (2) ŵ = 0.26 mm1
β = 102.581 (3)°T = 150 K
V = 1663.2 (5) Å3Prism, yellow
Z = 40.34 × 0.32 × 0.10 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
5291 independent reflections
Radiation source: sealed tube4023 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm-1Rint = 0.041
φ and ω scansθmax = 31.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 2121
Tmin = 0.885, Tmax = 0.975k = 1212
21434 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: mixed
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0464P)2 + 0.4383P]
where P = (Fo2 + 2Fc2)/3
5291 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.25 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.

Refinement. Compound #4

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.29234 (3)0.32109 (4)0.48615 (3)0.02725 (10)
O10.18273 (7)0.38773 (11)0.64208 (7)0.0241 (2)
O20.10261 (6)0.65866 (12)0.67309 (7)0.0239 (2)
O30.10408 (7)0.88836 (11)0.54071 (9)0.0302 (2)
O40.25869 (8)0.47397 (12)0.27145 (8)0.0320 (3)
O50.38442 (7)0.56929 (12)0.02661 (7)0.0249 (2)
N10.33695 (8)0.69571 (13)0.31234 (8)0.0191 (2)
H1A0.3526 (12)0.762 (2)0.3588 (13)0.026 (4)*
C10.23398 (9)0.60558 (15)0.42223 (10)0.0193 (2)
C20.23353 (9)0.48844 (14)0.49310 (10)0.0189 (2)
C30.18745 (9)0.50552 (14)0.57581 (10)0.0186 (2)
C40.14420 (9)0.64091 (15)0.58915 (10)0.0194 (2)
C50.14667 (9)0.76025 (15)0.51996 (10)0.0204 (2)
C60.19046 (9)0.74103 (15)0.43585 (10)0.0207 (3)
H6A0.1906000.8207830.3875830.025*
C70.25364 (12)0.39211 (18)0.73685 (12)0.0323 (3)
H7A0.2479230.3036260.7795830.048*
H7B0.2461220.4830710.7763840.048*
H7C0.3154080.3926390.7194410.048*
C80.00347 (10)0.62546 (17)0.64724 (12)0.0260 (3)
H8A0.0064690.5167300.6338780.031*
H8B0.0271860.6806430.5830950.031*
C90.03754 (11)0.6722 (2)0.73783 (14)0.0410 (4)
H9A0.1045760.6494640.7220870.061*
H9B0.0283570.7802380.7496970.061*
H9C0.0065310.6175410.8010300.061*
C100.12623 (12)1.02402 (17)0.49314 (14)0.0327 (3)
H10A0.1092551.1101960.5317600.049*
H10B0.0911991.0280740.4200610.049*
H10C0.1934191.0268580.4949740.049*
C110.27614 (9)0.58307 (16)0.32791 (10)0.0213 (3)
C120.38339 (9)0.70472 (14)0.22986 (10)0.0180 (2)
C130.36265 (9)0.61821 (15)0.14259 (10)0.0204 (3)
H13A0.3155540.5435650.1370430.024*
C140.41092 (9)0.63713 (15)0.05714 (10)0.0201 (2)
C150.49279 (10)0.74267 (18)0.07335 (11)0.0262 (3)
H15A0.4996870.7815660.0043570.031*
H15B0.5505110.6869240.1049060.031*
C160.48180 (11)0.87402 (17)0.14418 (11)0.0275 (3)
H16A0.4303040.9395260.1077460.033*
H16B0.5400600.9340010.1589340.033*
C170.46077 (10)0.81930 (16)0.24729 (11)0.0234 (3)
H17A0.5180060.7745460.2910630.028*
H17B0.4426540.9058880.2860320.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03470 (19)0.02092 (16)0.02974 (18)0.00364 (13)0.01494 (14)0.00058 (13)
O10.0298 (5)0.0226 (5)0.0213 (5)0.0047 (4)0.0089 (4)0.0046 (4)
O20.0204 (5)0.0342 (5)0.0200 (5)0.0020 (4)0.0107 (4)0.0029 (4)
O30.0330 (6)0.0225 (5)0.0407 (6)0.0067 (4)0.0200 (5)0.0031 (4)
O40.0448 (6)0.0290 (5)0.0281 (5)0.0144 (5)0.0210 (5)0.0079 (4)
O50.0320 (5)0.0273 (5)0.0173 (4)0.0001 (4)0.0092 (4)0.0014 (4)
N10.0220 (5)0.0222 (5)0.0153 (5)0.0033 (4)0.0087 (4)0.0023 (4)
C10.0192 (6)0.0227 (6)0.0177 (6)0.0027 (5)0.0076 (4)0.0000 (5)
C20.0194 (6)0.0191 (6)0.0202 (6)0.0008 (5)0.0085 (4)0.0009 (5)
C30.0189 (6)0.0203 (6)0.0176 (6)0.0035 (5)0.0065 (4)0.0012 (5)
C40.0187 (6)0.0239 (6)0.0173 (6)0.0023 (5)0.0075 (4)0.0007 (5)
C50.0181 (6)0.0215 (6)0.0227 (6)0.0005 (5)0.0071 (5)0.0002 (5)
C60.0205 (6)0.0222 (6)0.0206 (6)0.0003 (5)0.0072 (5)0.0039 (5)
C70.0401 (9)0.0305 (8)0.0242 (7)0.0003 (6)0.0026 (6)0.0077 (6)
C80.0210 (6)0.0297 (7)0.0301 (7)0.0005 (5)0.0114 (5)0.0007 (6)
C90.0256 (8)0.0645 (12)0.0379 (9)0.0013 (8)0.0178 (7)0.0059 (8)
C100.0356 (8)0.0216 (7)0.0420 (9)0.0061 (6)0.0107 (7)0.0059 (6)
C110.0230 (6)0.0242 (6)0.0190 (6)0.0021 (5)0.0094 (5)0.0011 (5)
C120.0183 (6)0.0206 (6)0.0165 (5)0.0011 (4)0.0065 (4)0.0028 (4)
C130.0217 (6)0.0245 (6)0.0165 (6)0.0025 (5)0.0072 (4)0.0009 (5)
C140.0220 (6)0.0229 (6)0.0165 (6)0.0032 (5)0.0065 (4)0.0027 (5)
C150.0258 (7)0.0357 (8)0.0202 (6)0.0046 (6)0.0116 (5)0.0005 (6)
C160.0305 (7)0.0290 (7)0.0263 (7)0.0101 (6)0.0132 (6)0.0001 (6)
C170.0240 (6)0.0274 (7)0.0208 (6)0.0066 (5)0.0096 (5)0.0030 (5)
Geometric parameters (Å, º) top
Cl1—C21.7352 (13)C8—C91.497 (2)
O1—C31.3714 (15)C8—H8A0.9900
O1—C71.4317 (18)C8—H8B0.9900
O2—C41.3734 (14)C9—H9A0.9800
O2—C81.4486 (16)C9—H9B0.9800
O3—C51.3567 (16)C9—H9C0.9800
O3—C101.4285 (18)C10—H10A0.9800
O4—C111.2132 (17)C10—H10B0.9800
O5—C141.2350 (16)C10—H10C0.9800
N1—C111.3865 (17)C12—C131.3536 (18)
N1—C121.3950 (15)C12—C171.5061 (18)
N1—H1A0.844 (18)C13—C141.4543 (17)
C1—C61.3949 (18)C13—H13A0.9500
C1—C21.3956 (18)C14—C151.5029 (19)
C1—C111.5056 (17)C15—C161.522 (2)
C2—C31.4001 (16)C15—H15A0.9900
C3—C41.3917 (18)C15—H15B0.9900
C4—C51.4008 (19)C16—C171.5241 (19)
C5—C61.3969 (17)C16—H16A0.9900
C6—H6A0.9500C16—H16B0.9900
C7—H7A0.9800C17—H17A0.9900
C7—H7B0.9800C17—H17B0.9900
C7—H7C0.9800
C3—O1—C7113.37 (11)C8—C9—H9C109.5
C4—O2—C8112.80 (10)H9A—C9—H9C109.5
C5—O3—C10117.91 (11)H9B—C9—H9C109.5
C11—N1—C12126.28 (11)O3—C10—H10A109.5
C11—N1—H1A119.2 (12)O3—C10—H10B109.5
C12—N1—H1A114.3 (12)H10A—C10—H10B109.5
C6—C1—C2119.68 (11)O3—C10—H10C109.5
C6—C1—C11119.99 (11)H10A—C10—H10C109.5
C2—C1—C11120.24 (12)H10B—C10—H10C109.5
C1—C2—C3120.11 (12)O4—C11—N1123.29 (11)
C1—C2—Cl1122.32 (9)O4—C11—C1122.22 (12)
C3—C2—Cl1117.53 (10)N1—C11—C1114.48 (11)
O1—C3—C4119.88 (11)C13—C12—N1123.91 (12)
O1—C3—C2120.10 (11)C13—C12—C17122.49 (11)
C4—C3—C2119.99 (11)N1—C12—C17113.59 (11)
O2—C4—C3119.54 (11)C12—C13—C14121.39 (12)
O2—C4—C5120.30 (12)C12—C13—H13A119.3
C3—C4—C5120.11 (11)C14—C13—H13A119.3
O3—C5—C6124.74 (12)O5—C14—C13120.63 (12)
O3—C5—C4115.67 (11)O5—C14—C15121.24 (11)
C6—C5—C4119.59 (12)C13—C14—C15118.12 (11)
C1—C6—C5120.47 (12)C14—C15—C16112.36 (11)
C1—C6—H6A119.8C14—C15—H15A109.1
C5—C6—H6A119.8C16—C15—H15A109.1
O1—C7—H7A109.5C14—C15—H15B109.1
O1—C7—H7B109.5C16—C15—H15B109.1
H7A—C7—H7B109.5H15A—C15—H15B107.9
O1—C7—H7C109.5C15—C16—C17110.98 (12)
H7A—C7—H7C109.5C15—C16—H16A109.4
H7B—C7—H7C109.5C17—C16—H16A109.4
O2—C8—C9108.30 (12)C15—C16—H16B109.4
O2—C8—H8A110.0C17—C16—H16B109.4
C9—C8—H8A110.0H16A—C16—H16B108.0
O2—C8—H8B110.0C12—C17—C16111.97 (11)
C9—C8—H8B110.0C12—C17—H17A109.2
H8A—C8—H8B108.4C16—C17—H17A109.2
C8—C9—H9A109.5C12—C17—H17B109.2
C8—C9—H9B109.5C16—C17—H17B109.2
H9A—C9—H9B109.5H17A—C17—H17B107.9
C6—C1—C2—C31.71 (19)C11—C1—C6—C5176.51 (12)
C11—C1—C2—C3174.66 (12)O3—C5—C6—C1178.77 (13)
C6—C1—C2—Cl1175.87 (10)C4—C5—C6—C11.9 (2)
C11—C1—C2—Cl17.76 (18)C4—O2—C8—C9170.82 (13)
C7—O1—C3—C485.34 (15)C12—N1—C11—O42.7 (2)
C7—O1—C3—C296.38 (15)C12—N1—C11—C1178.18 (12)
C1—C2—C3—O1176.51 (12)C6—C1—C11—O4129.20 (15)
Cl1—C2—C3—O15.80 (17)C2—C1—C11—O447.2 (2)
C1—C2—C3—C41.77 (19)C6—C1—C11—N151.64 (17)
Cl1—C2—C3—C4175.92 (10)C2—C1—C11—N1132.00 (13)
C8—O2—C4—C394.55 (14)C11—N1—C12—C1312.4 (2)
C8—O2—C4—C588.21 (15)C11—N1—C12—C17166.70 (13)
O1—C3—C4—O24.46 (18)N1—C12—C13—C14177.36 (12)
C2—C3—C4—O2177.25 (11)C17—C12—C13—C143.6 (2)
O1—C3—C4—C5178.29 (12)C12—C13—C14—O5171.94 (13)
C2—C3—C4—C50.01 (19)C12—C13—C14—C157.3 (2)
C10—O3—C5—C618.0 (2)O5—C14—C15—C16146.86 (13)
C10—O3—C5—C4162.68 (13)C13—C14—C15—C1632.36 (18)
O2—C4—C5—O31.55 (19)C14—C15—C16—C1752.88 (17)
C3—C4—C5—O3178.78 (12)C13—C12—C17—C1624.94 (19)
O2—C4—C5—C6179.06 (12)N1—C12—C17—C16155.90 (12)
C3—C4—C5—C61.8 (2)C15—C16—C17—C1248.67 (17)
C2—C1—C6—C50.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O5i0.844 (18)2.098 (18)2.9410 (15)177.1 (16)
C7—H7A···Cl1ii0.982.863.7022 (16)145
C7—H7A···O4ii0.982.483.293 (2)140
C9—H9A···O4iii0.982.533.470 (2)161
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y+1, z+1.
2-Chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide (3b) top
Crystal data top
C19H24ClNO5F(000) = 1616
Mr = 381.84Dx = 1.292 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.6986 (13) ÅCell parameters from 23388 reflections
b = 10.6309 (10) Åθ = 2.4–31.0°
c = 25.131 (2) ŵ = 0.22 mm1
β = 90.1851 (14)°T = 150 K
V = 3926.9 (6) Å3Prism, colourless
Z = 80.48 × 0.44 × 0.21 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
12630 independent reflections
Radiation source: sealed tube10320 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm-1Rint = 0.026
φ and ω scansθmax = 31.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 2121
Tmin = 0.841, Tmax = 0.954k = 1515
67292 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: mixed
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0599P)2 + 1.0458P]
where P = (Fo2 + 2Fc2)/3
12630 reflections(Δ/σ)max = 0.006
584 parametersΔρmax = 0.64 e Å3
399 restraintsΔρmin = 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.

Refinement. Compound #6

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A0.74167 (2)1.06636 (3)0.50622 (2)0.03341 (7)
O1A0.85300 (6)0.92470 (9)0.43031 (3)0.03358 (19)
O2A0.96808 (6)0.73233 (10)0.45218 (4)0.0371 (2)
O3A0.98422 (6)0.64044 (10)0.55396 (4)0.0411 (2)
O4A0.79762 (5)0.97694 (9)0.66166 (3)0.03064 (18)
O5A0.54514 (6)1.01715 (10)0.78213 (3)0.0376 (2)
N1A0.67015 (6)0.94345 (9)0.61067 (4)0.02155 (17)
H1AA0.6506 (11)0.9153 (15)0.5810 (7)0.034 (4)*
C1A0.81762 (7)0.89610 (10)0.57423 (4)0.02277 (19)
C2A0.81118 (7)0.94022 (11)0.52235 (4)0.0245 (2)
C3A0.86370 (7)0.88575 (12)0.48185 (4)0.0272 (2)
C4A0.92222 (7)0.78611 (12)0.49363 (5)0.0293 (2)
C5A0.92801 (7)0.74122 (12)0.54613 (5)0.0293 (2)
C6A0.87719 (7)0.79758 (11)0.58605 (4)0.0263 (2)
H6AA0.8829940.7688780.6216950.032*
C7A0.91558 (11)1.01997 (17)0.41412 (5)0.0474 (4)
H7AA0.9032361.0433800.3770780.071*
H7AB0.9778790.9878950.4171980.071*
H7AC0.9085511.0939940.4369810.071*
C8A1.06559 (9)0.7271 (2)0.45645 (6)0.0624 (5)
H8AA1.0839770.6472580.4736680.075*
H8AB1.0875440.7975090.4788640.075*
C9A1.10703 (11)0.7356 (2)0.40297 (7)0.0628 (5)
H9AA1.1727510.7214180.4057970.094*
H9AB1.0957070.8192840.3880250.094*
H9AC1.0800690.6716100.3796850.094*
C10A0.99347 (11)0.59578 (18)0.60744 (7)0.0550 (4)
H10A1.0335980.5221730.6079830.082*
H10B0.9335240.5722830.6212090.082*
H10C1.0196100.6623030.6297350.082*
C11A0.76218 (7)0.94515 (10)0.61997 (4)0.02202 (19)
C12A0.60074 (6)0.97178 (10)0.64589 (4)0.02102 (18)
C13A0.61233 (7)0.98962 (10)0.69867 (4)0.02312 (19)
H13A0.6719610.9873780.7133410.028*
C14A0.53549 (7)1.01213 (11)0.73334 (4)0.0258 (2)
C15A0.44417 (8)1.03239 (13)0.70805 (5)0.0322 (2)
H15A0.4374921.1224770.6988500.039*
H15C0.3961691.0110490.7340770.039*
C16A0.43022 (7)0.95307 (15)0.65763 (5)0.0363 (3)
C17A0.50923 (7)0.98156 (14)0.61962 (4)0.0327 (3)
H17A0.5067110.9220340.5893520.039*
H17B0.5016341.0675880.6051910.039*
C18A0.34099 (9)0.9921 (3)0.63114 (6)0.0782 (8)
H18A0.2906870.9796650.6560990.117*
H18B0.3307830.9405980.5993230.117*
H18C0.3442031.0809520.6209910.117*
C19A0.42926 (11)0.81411 (18)0.67166 (7)0.0577 (5)
H19A0.3809730.7978140.6975610.087*
H19B0.4881560.7903430.6870290.087*
H19C0.4180200.7644970.6394320.087*
Cl1B0.33068 (2)0.36791 (3)0.37042 (2)0.03251 (7)
O1B0.19443 (6)0.32113 (8)0.28774 (3)0.03058 (17)
O2B0.12498 (6)0.49472 (9)0.21650 (3)0.03228 (18)
O3B0.17637 (6)0.73524 (8)0.22015 (3)0.03071 (18)
O4B0.35516 (6)0.74079 (10)0.40209 (4)0.0415 (2)
C1B0.31411 (6)0.60638 (10)0.33084 (4)0.02011 (18)
C2B0.28768 (7)0.48116 (10)0.32756 (4)0.02208 (19)
C3B0.22268 (7)0.44399 (10)0.28987 (4)0.02362 (19)
C4B0.18562 (7)0.53194 (11)0.25503 (4)0.0240 (2)
C5B0.21397 (7)0.65796 (10)0.25735 (4)0.02301 (19)
C6B0.27647 (7)0.69485 (10)0.29595 (4)0.02189 (18)
H6BA0.2937250.7807330.2986450.026*
C7B0.23634 (11)0.25212 (13)0.24515 (7)0.0436 (3)
H7BA0.2153240.1646580.2459360.065*
H7BB0.3026050.2542940.2494830.065*
H7BC0.2196490.2903790.2110100.065*
C8B0.03306 (9)0.47519 (14)0.23569 (6)0.0416 (3)
H8BA0.0346650.4166370.2663150.050*
H8BB0.0038210.4356960.2072050.050*
C9B0.01135 (10)0.59598 (18)0.25249 (10)0.0675 (6)
H9BA0.0729820.5785210.2652780.101*
H9BB0.0144470.6534900.2220610.101*
H9BC0.0244140.6347580.2810910.101*
C10B0.20442 (9)0.86380 (11)0.22096 (5)0.0310 (2)
H10D0.1730440.9099340.1925670.047*
H10E0.2702990.8686150.2154240.047*
H10F0.1891850.9011080.2554640.047*
C11B0.37827 (7)0.65588 (10)0.37276 (4)0.02269 (19)
O5B0.5926 (5)0.7923 (8)0.5286 (3)0.0383 (12)0.551 (2)
N1B0.4614 (6)0.6071 (10)0.3766 (4)0.0274 (15)0.551 (2)
H1BA0.471 (3)0.552 (4)0.3576 (18)0.026 (13)*0.551 (2)
C12B0.5307 (6)0.6264 (11)0.4131 (5)0.0259 (10)0.551 (2)
C13B0.5224 (5)0.7057 (8)0.4537 (3)0.0210 (9)0.551 (2)
H13B0.4660930.7467000.4601770.025*0.551 (2)
C14B0.6004 (6)0.7288 (8)0.4881 (4)0.0293 (11)0.551 (2)
C15B0.69268 (14)0.6766 (2)0.47298 (9)0.0304 (5)0.551 (2)
H15B0.7295000.6652060.5056840.036*0.551 (2)
H15D0.7243670.7385540.4501900.036*0.551 (2)
C16B0.6870 (4)0.5507 (7)0.4434 (3)0.0262 (9)0.551 (2)
C17B0.62225 (13)0.5682 (2)0.39563 (8)0.0261 (4)0.551 (2)
H17C0.6108860.4856220.3786360.031*0.551 (2)
H17D0.6513460.6236240.3689930.031*0.551 (2)
C18B0.65099 (17)0.4478 (2)0.48043 (10)0.0384 (5)0.551 (2)
H18D0.6929490.4371440.5104800.058*0.551 (2)
H18E0.6461480.3683750.4607970.058*0.551 (2)
H18F0.5908750.4719310.4937230.058*0.551 (2)
C19B0.78134 (15)0.5136 (3)0.42324 (10)0.0436 (7)0.551 (2)
H19D0.8235510.5077980.4534100.065*0.551 (2)
H19E0.8031550.5773840.3981770.065*0.551 (2)
H19F0.7777910.4319640.4052630.065*0.551 (2)
O5C0.6059 (7)0.7977 (10)0.5201 (4)0.0413 (15)0.449 (2)
N1C0.4643 (5)0.5949 (11)0.3708 (4)0.0156 (9)0.449 (2)
H1CA0.476 (3)0.549 (4)0.3423 (18)0.019 (12)*0.449 (2)
C12C0.5324 (8)0.6138 (14)0.4091 (6)0.0262 (12)0.449 (2)
C13C0.5340 (6)0.6981 (11)0.4488 (4)0.0268 (13)0.449 (2)
H13C0.4851650.7564760.4508180.032*0.449 (2)
C14C0.6048 (7)0.7067 (10)0.4889 (5)0.0310 (13)0.449 (2)
C15C0.67207 (18)0.6008 (3)0.49113 (11)0.0341 (6)0.449 (2)
H15E0.6496820.5363540.5163270.041*0.449 (2)
H15F0.7305530.6332840.5051440.041*0.449 (2)
C16C0.6890 (6)0.5385 (9)0.4371 (4)0.0293 (12)0.449 (2)
C17C0.59763 (16)0.5023 (2)0.41227 (10)0.0244 (5)0.449 (2)
H17E0.6079930.4689610.3760090.029*0.449 (2)
H17F0.5695010.4347000.4337300.029*0.449 (2)
C18C0.7464 (2)0.4183 (3)0.44515 (14)0.0434 (8)0.449 (2)
H18G0.8064030.4410800.4592040.065*0.449 (2)
H18H0.7534840.3750200.4109760.065*0.449 (2)
H18I0.7156140.3624310.4703710.065*0.449 (2)
C19C0.74033 (19)0.6285 (3)0.39994 (12)0.0373 (7)0.449 (2)
H19G0.7069200.7080070.3971460.056*0.449 (2)
H19H0.7455730.5903070.3645840.056*0.449 (2)
H19I0.8012410.6445310.4143780.056*0.449 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.03295 (13)0.04046 (16)0.02684 (13)0.00661 (11)0.00220 (10)0.00619 (11)
O1A0.0289 (4)0.0525 (5)0.0193 (4)0.0066 (4)0.0016 (3)0.0010 (4)
O2A0.0223 (4)0.0560 (6)0.0330 (4)0.0005 (4)0.0088 (3)0.0150 (4)
O3A0.0336 (4)0.0458 (5)0.0439 (5)0.0154 (4)0.0105 (4)0.0032 (4)
O4A0.0233 (3)0.0448 (5)0.0238 (4)0.0036 (3)0.0004 (3)0.0060 (3)
O5A0.0335 (4)0.0616 (6)0.0178 (4)0.0051 (4)0.0043 (3)0.0003 (4)
N1A0.0193 (4)0.0277 (4)0.0176 (4)0.0009 (3)0.0024 (3)0.0040 (3)
C1A0.0181 (4)0.0292 (5)0.0211 (4)0.0022 (4)0.0033 (3)0.0018 (4)
C2A0.0195 (4)0.0320 (5)0.0220 (5)0.0011 (4)0.0017 (3)0.0000 (4)
C3A0.0208 (4)0.0409 (6)0.0200 (5)0.0046 (4)0.0029 (4)0.0032 (4)
C4A0.0189 (4)0.0416 (6)0.0274 (5)0.0031 (4)0.0070 (4)0.0080 (5)
C5A0.0200 (4)0.0353 (6)0.0326 (6)0.0019 (4)0.0053 (4)0.0016 (5)
C6A0.0196 (4)0.0340 (6)0.0252 (5)0.0002 (4)0.0042 (4)0.0016 (4)
C7A0.0488 (8)0.0673 (10)0.0262 (6)0.0183 (7)0.0043 (5)0.0060 (6)
C8A0.0219 (6)0.1254 (17)0.0400 (8)0.0095 (8)0.0090 (5)0.0176 (9)
C9A0.0377 (7)0.0939 (14)0.0570 (10)0.0074 (8)0.0225 (7)0.0248 (10)
C10A0.0494 (8)0.0604 (10)0.0552 (9)0.0266 (8)0.0120 (7)0.0177 (8)
C11A0.0197 (4)0.0250 (5)0.0213 (4)0.0013 (3)0.0031 (3)0.0002 (4)
C12A0.0201 (4)0.0228 (5)0.0202 (4)0.0008 (3)0.0031 (3)0.0002 (4)
C13A0.0214 (4)0.0287 (5)0.0193 (4)0.0013 (4)0.0018 (3)0.0004 (4)
C14A0.0266 (5)0.0311 (5)0.0199 (5)0.0002 (4)0.0039 (4)0.0008 (4)
C15A0.0273 (5)0.0462 (7)0.0232 (5)0.0103 (5)0.0048 (4)0.0002 (5)
C16A0.0187 (4)0.0670 (9)0.0232 (5)0.0029 (5)0.0020 (4)0.0056 (5)
C17A0.0219 (5)0.0560 (8)0.0201 (5)0.0068 (5)0.0006 (4)0.0016 (5)
C18A0.0225 (6)0.180 (2)0.0325 (7)0.0184 (10)0.0011 (5)0.0117 (11)
C19A0.0454 (8)0.0640 (11)0.0639 (10)0.0278 (7)0.0217 (7)0.0218 (8)
Cl1B0.03134 (13)0.03067 (14)0.03546 (15)0.00338 (10)0.00739 (11)0.01257 (11)
O1B0.0322 (4)0.0260 (4)0.0335 (4)0.0104 (3)0.0015 (3)0.0034 (3)
O2B0.0319 (4)0.0379 (5)0.0270 (4)0.0106 (3)0.0110 (3)0.0017 (3)
O3B0.0340 (4)0.0294 (4)0.0287 (4)0.0042 (3)0.0122 (3)0.0075 (3)
O4B0.0345 (4)0.0486 (6)0.0412 (5)0.0168 (4)0.0129 (4)0.0232 (4)
C1B0.0169 (4)0.0262 (5)0.0172 (4)0.0002 (3)0.0008 (3)0.0015 (4)
C2B0.0195 (4)0.0258 (5)0.0209 (4)0.0007 (3)0.0004 (3)0.0043 (4)
C3B0.0222 (4)0.0248 (5)0.0239 (5)0.0057 (4)0.0008 (4)0.0015 (4)
C4B0.0214 (4)0.0296 (5)0.0209 (5)0.0053 (4)0.0030 (3)0.0004 (4)
C5B0.0223 (4)0.0262 (5)0.0205 (4)0.0012 (4)0.0023 (3)0.0029 (4)
C6B0.0211 (4)0.0229 (5)0.0217 (4)0.0012 (3)0.0013 (3)0.0001 (4)
C7B0.0510 (8)0.0262 (6)0.0538 (9)0.0048 (5)0.0071 (6)0.0044 (6)
C8B0.0284 (6)0.0426 (7)0.0536 (8)0.0126 (5)0.0136 (5)0.0074 (6)
C9B0.0263 (6)0.0535 (10)0.1226 (18)0.0024 (6)0.0072 (8)0.0030 (11)
C10B0.0358 (6)0.0266 (5)0.0306 (6)0.0012 (4)0.0068 (4)0.0051 (4)
C11B0.0206 (4)0.0276 (5)0.0199 (4)0.0015 (4)0.0020 (3)0.0019 (4)
O5B0.044 (3)0.0460 (17)0.025 (2)0.0018 (18)0.0094 (18)0.0140 (14)
N1B0.0313 (19)0.034 (2)0.0166 (19)0.0050 (12)0.0028 (10)0.0165 (13)
C12B0.0168 (14)0.039 (3)0.022 (2)0.0082 (14)0.0033 (13)0.0089 (15)
C13B0.0186 (16)0.0277 (16)0.0168 (14)0.0033 (13)0.0052 (14)0.0116 (11)
C14B0.0250 (14)0.036 (2)0.0273 (17)0.0022 (14)0.0035 (11)0.0064 (16)
C15B0.0246 (9)0.0413 (12)0.0254 (9)0.0051 (8)0.0078 (7)0.0024 (9)
C16B0.0154 (13)0.0386 (19)0.0245 (18)0.0026 (12)0.0049 (11)0.0001 (14)
C17B0.0198 (8)0.0370 (11)0.0216 (9)0.0018 (7)0.0014 (7)0.0058 (8)
C18B0.0415 (12)0.0370 (12)0.0367 (12)0.0060 (9)0.0004 (9)0.0069 (9)
C19B0.0224 (9)0.0731 (19)0.0351 (12)0.0124 (10)0.0029 (8)0.0055 (12)
O5C0.039 (2)0.059 (2)0.026 (3)0.0141 (15)0.0007 (16)0.0192 (19)
N1C0.0102 (13)0.025 (2)0.012 (2)0.0063 (12)0.0053 (14)0.0123 (18)
C12C0.028 (2)0.035 (2)0.0154 (18)0.0042 (16)0.0047 (15)0.0139 (15)
C13C0.024 (2)0.029 (2)0.028 (2)0.0077 (15)0.0039 (15)0.0020 (16)
C14C0.034 (2)0.039 (3)0.0197 (18)0.0018 (18)0.0065 (15)0.009 (2)
C15C0.0299 (12)0.0471 (16)0.0252 (12)0.0027 (11)0.0088 (9)0.0059 (11)
C16C0.029 (2)0.035 (2)0.024 (2)0.0004 (15)0.0035 (15)0.0040 (16)
C17C0.0234 (10)0.0253 (11)0.0246 (11)0.0024 (9)0.0036 (8)0.0028 (9)
C18C0.0343 (14)0.0524 (18)0.0434 (17)0.0172 (13)0.0090 (12)0.0012 (14)
C19C0.0297 (12)0.0467 (16)0.0356 (14)0.0080 (11)0.0034 (10)0.0072 (12)
Geometric parameters (Å, º) top
Cl1A—C2A1.7331 (12)C3B—C4B1.3908 (15)
O1A—C3A1.3684 (14)C4B—C5B1.4042 (15)
O1A—C7A1.4281 (17)C5B—C6B1.3903 (14)
O2A—C4A1.3678 (13)C6B—H6BA0.9500
O2A—C8A1.4381 (16)C7B—H7BA0.9800
O3A—C5A1.3667 (15)C7B—H7BB0.9800
O3A—C10A1.4313 (19)C7B—H7BC0.9800
O4A—C11A1.2163 (13)C8B—C9B1.502 (2)
O5A—C14A1.2349 (13)C8B—H8BA0.9900
N1A—C11A1.3722 (13)C8B—H8BB0.9900
N1A—C12A1.3859 (12)C9B—H9BA0.9800
N1A—H1AA0.853 (16)C9B—H9BB0.9800
C1A—C2A1.3885 (15)C9B—H9BC0.9800
C1A—C6A1.3964 (15)C10B—H10D0.9800
C1A—C11A1.5047 (14)C10B—H10E0.9800
C2A—C3A1.4044 (15)C10B—H10F0.9800
C3A—C4A1.3956 (17)C11B—N1B1.330 (8)
C4A—C5A1.4053 (17)C11B—N1C1.421 (8)
C5A—C6A1.3886 (15)O5B—C14B1.229 (8)
C6A—H6AA0.9500N1B—C12B1.384 (8)
C7A—H7AA0.9800N1B—H1BA0.77 (5)
C7A—H7AB0.9800C12B—C13B1.330 (7)
C7A—H7AC0.9800C12B—C17B1.545 (8)
C8A—C9A1.480 (2)C13B—C14B1.455 (7)
C8A—H8AA0.9900C13B—H13B0.9500
C8A—H8AB0.9900C14B—C15B1.515 (8)
C9A—H9AA0.9800C15B—C16B1.535 (7)
C9A—H9AB0.9800C15B—H15B0.9900
C9A—H9AC0.9800C15B—H15D0.9900
C10A—H10A0.9800C16B—C19B1.530 (7)
C10A—H10B0.9800C16B—C18B1.532 (8)
C10A—H10C0.9800C16B—C17B1.540 (6)
C12A—C13A1.3501 (14)C17B—H17C0.9900
C12A—C17A1.5001 (15)C17B—H17D0.9900
C13A—C14A1.4486 (14)C18B—H18D0.9800
C13A—H13A0.9500C18B—H18E0.9800
C14A—C15A1.4989 (16)C18B—H18F0.9800
C15A—C16A1.5351 (18)C19B—H19D0.9800
C15A—H15A0.9900C19B—H19E0.9800
C15A—H15C0.9900C19B—H19F0.9800
C16A—C19A1.519 (2)O5C—C14C1.244 (9)
C16A—C18A1.5263 (19)N1C—C12C1.401 (9)
C16A—C17A1.5364 (16)N1C—H1CA0.88 (5)
C17A—H17A0.9900C12C—C13C1.342 (9)
C17A—H17B0.9900C12C—C17C1.527 (10)
C18A—H18A0.9800C13C—C14C1.450 (9)
C18A—H18B0.9800C13C—H13C0.9500
C18A—H18C0.9800C14C—C15C1.499 (8)
C19A—H19A0.9800C15C—C16C1.532 (9)
C19A—H19B0.9800C15C—H15E0.9900
C19A—H19C0.9800C15C—H15F0.9900
Cl1B—C2B1.7334 (11)C16C—C17C1.528 (9)
O1B—C3B1.3715 (13)C16C—C19C1.537 (10)
O1B—C7B1.4379 (17)C16C—C18C1.545 (9)
O2B—C4B1.3724 (12)C17C—H17E0.9900
O2B—C8B1.4510 (16)C17C—H17F0.9900
O3B—C5B1.3605 (13)C18C—H18G0.9800
O3B—C10B1.4277 (14)C18C—H18H0.9800
O4B—C11B1.2147 (13)C18C—H18I0.9800
C1B—C2B1.3891 (15)C19C—H19G0.9800
C1B—C6B1.3986 (14)C19C—H19H0.9800
C1B—C11B1.5065 (14)C19C—H19I0.9800
C2B—C3B1.4000 (14)
C3A—O1A—C7A114.34 (10)O1B—C7B—H7BB109.5
C4A—O2A—C8A116.92 (10)H7BA—C7B—H7BB109.5
C5A—O3A—C10A116.80 (10)O1B—C7B—H7BC109.5
C11A—N1A—C12A127.99 (9)H7BA—C7B—H7BC109.5
C11A—N1A—H1AA118.9 (11)H7BB—C7B—H7BC109.5
C12A—N1A—H1AA112.8 (11)O2B—C8B—C9B112.15 (12)
C2A—C1A—C6A119.60 (10)O2B—C8B—H8BA109.2
C2A—C1A—C11A124.39 (10)C9B—C8B—H8BA109.2
C6A—C1A—C11A115.99 (9)O2B—C8B—H8BB109.2
C1A—C2A—C3A120.34 (10)C9B—C8B—H8BB109.2
C1A—C2A—Cl1A121.28 (8)H8BA—C8B—H8BB107.9
C3A—C2A—Cl1A118.34 (9)C8B—C9B—H9BA109.5
O1A—C3A—C4A119.96 (10)C8B—C9B—H9BB109.5
O1A—C3A—C2A119.96 (11)H9BA—C9B—H9BB109.5
C4A—C3A—C2A119.94 (10)C8B—C9B—H9BC109.5
O2A—C4A—C3A117.42 (11)H9BA—C9B—H9BC109.5
O2A—C4A—C5A122.99 (11)H9BB—C9B—H9BC109.5
C3A—C4A—C5A119.50 (10)O3B—C10B—H10D109.5
O3A—C5A—C6A124.09 (11)O3B—C10B—H10E109.5
O3A—C5A—C4A115.87 (10)H10D—C10B—H10E109.5
C6A—C5A—C4A120.03 (11)O3B—C10B—H10F109.5
C5A—C6A—C1A120.56 (11)H10D—C10B—H10F109.5
C5A—C6A—H6AA119.7H10E—C10B—H10F109.5
C1A—C6A—H6AA119.7O4B—C11B—N1B120.3 (4)
O1A—C7A—H7AA109.5O4B—C11B—N1C127.6 (4)
O1A—C7A—H7AB109.5O4B—C11B—C1B120.55 (9)
H7AA—C7A—H7AB109.5N1B—C11B—C1B119.1 (4)
O1A—C7A—H7AC109.5N1C—C11B—C1B111.8 (4)
H7AA—C7A—H7AC109.5C11B—N1B—C12B131.6 (8)
H7AB—C7A—H7AC109.5C11B—N1B—H1BA115 (4)
O2A—C8A—C9A110.05 (14)C12B—N1B—H1BA112 (4)
O2A—C8A—H8AA109.7C13B—C12B—N1B122.2 (7)
C9A—C8A—H8AA109.7C13B—C12B—C17B123.6 (6)
O2A—C8A—H8AB109.7N1B—C12B—C17B113.1 (6)
C9A—C8A—H8AB109.7C12B—C13B—C14B119.3 (6)
H8AA—C8A—H8AB108.2C12B—C13B—H13B120.4
C8A—C9A—H9AA109.5C14B—C13B—H13B120.4
C8A—C9A—H9AB109.5O5B—C14B—C13B120.7 (7)
H9AA—C9A—H9AB109.5O5B—C14B—C15B119.7 (7)
C8A—C9A—H9AC109.5C13B—C14B—C15B119.6 (6)
H9AA—C9A—H9AC109.5C14B—C15B—C16B113.2 (4)
H9AB—C9A—H9AC109.5C14B—C15B—H15B108.9
O3A—C10A—H10A109.5C16B—C15B—H15B108.9
O3A—C10A—H10B109.5C14B—C15B—H15D108.9
H10A—C10A—H10B109.5C16B—C15B—H15D108.9
O3A—C10A—H10C109.5H15B—C15B—H15D107.8
H10A—C10A—H10C109.5C19B—C16B—C18B109.4 (4)
H10B—C10A—H10C109.5C19B—C16B—C15B109.7 (4)
O4A—C11A—N1A124.73 (9)C18B—C16B—C15B110.3 (4)
O4A—C11A—C1A121.52 (9)C19B—C16B—C17B109.4 (4)
N1A—C11A—C1A113.66 (9)C18B—C16B—C17B110.3 (4)
C13A—C12A—N1A124.56 (9)C15B—C16B—C17B107.8 (4)
C13A—C12A—C17A122.20 (9)C16B—C17B—C12B111.3 (4)
N1A—C12A—C17A113.25 (9)C16B—C17B—H17C109.4
C12A—C13A—C14A121.19 (10)C12B—C17B—H17C109.4
C12A—C13A—H13A119.4C16B—C17B—H17D109.4
C14A—C13A—H13A119.4C12B—C17B—H17D109.4
O5A—C14A—C13A121.13 (10)H17C—C17B—H17D108.0
O5A—C14A—C15A120.98 (10)C16B—C18B—H18D109.5
C13A—C14A—C15A117.88 (9)C16B—C18B—H18E109.5
C14A—C15A—C16A112.84 (9)H18D—C18B—H18E109.5
C14A—C15A—H15A109.0C16B—C18B—H18F109.5
C16A—C15A—H15A109.0H18D—C18B—H18F109.5
C14A—C15A—H15C109.0H18E—C18B—H18F109.5
C16A—C15A—H15C109.0C16B—C19B—H19D109.5
H15A—C15A—H15C107.8C16B—C19B—H19E109.5
C19A—C16A—C18A110.90 (16)H19D—C19B—H19E109.5
C19A—C16A—C15A110.13 (12)C16B—C19B—H19F109.5
C18A—C16A—C15A108.85 (12)H19D—C19B—H19F109.5
C19A—C16A—C17A110.10 (11)H19E—C19B—H19F109.5
C18A—C16A—C17A108.99 (12)C12C—N1C—C11B123.0 (9)
C15A—C16A—C17A107.80 (11)C12C—N1C—H1CA119 (3)
C12A—C17A—C16A113.03 (9)C11B—N1C—H1CA117 (3)
C12A—C17A—H17A109.0C13C—C12C—N1C128.2 (9)
C16A—C17A—H17A109.0C13C—C12C—C17C118.0 (8)
C12A—C17A—H17B109.0N1C—C12C—C17C111.9 (7)
C16A—C17A—H17B109.0C12C—C13C—C14C124.8 (8)
H17A—C17A—H17B107.8C12C—C13C—H13C117.6
C16A—C18A—H18A109.5C14C—C13C—H13C117.6
C16A—C18A—H18B109.5O5C—C14C—C13C119.6 (9)
H18A—C18A—H18B109.5O5C—C14C—C15C123.6 (8)
C16A—C18A—H18C109.5C13C—C14C—C15C116.8 (7)
H18A—C18A—H18C109.5C14C—C15C—C16C113.6 (5)
H18B—C18A—H18C109.5C14C—C15C—H15E108.8
C16A—C19A—H19A109.5C16C—C15C—H15E108.8
C16A—C19A—H19B109.5C14C—C15C—H15F108.8
H19A—C19A—H19B109.5C16C—C15C—H15F108.8
C16A—C19A—H19C109.5H15E—C15C—H15F107.7
H19A—C19A—H19C109.5C17C—C16C—C15C109.0 (6)
H19B—C19A—H19C109.5C17C—C16C—C19C110.0 (6)
C3B—O1B—C7B112.62 (9)C15C—C16C—C19C110.6 (6)
C4B—O2B—C8B114.21 (10)C17C—C16C—C18C108.9 (6)
C5B—O3B—C10B116.84 (9)C15C—C16C—C18C109.4 (6)
C2B—C1B—C6B119.81 (9)C19C—C16C—C18C109.0 (6)
C2B—C1B—C11B123.40 (9)C12C—C17C—C16C112.2 (6)
C6B—C1B—C11B116.68 (9)C12C—C17C—H17E109.2
C1B—C2B—C3B120.05 (9)C16C—C17C—H17E109.2
C1B—C2B—Cl1B121.83 (8)C12C—C17C—H17F109.2
C3B—C2B—Cl1B118.10 (8)C16C—C17C—H17F109.2
O1B—C3B—C4B119.85 (9)H17E—C17C—H17F107.9
O1B—C3B—C2B120.07 (10)C16C—C18C—H18G109.5
C4B—C3B—C2B120.08 (10)C16C—C18C—H18H109.5
O2B—C4B—C3B120.17 (10)H18G—C18C—H18H109.5
O2B—C4B—C5B119.75 (10)C16C—C18C—H18I109.5
C3B—C4B—C5B119.98 (9)H18G—C18C—H18I109.5
O3B—C5B—C6B125.11 (10)H18H—C18C—H18I109.5
O3B—C5B—C4B115.33 (9)C16C—C19C—H19G109.5
C6B—C5B—C4B119.56 (10)C16C—C19C—H19H109.5
C5B—C6B—C1B120.46 (10)H19G—C19C—H19H109.5
C5B—C6B—H6BA119.8C16C—C19C—H19I109.5
C1B—C6B—H6BA119.8H19G—C19C—H19I109.5
O1B—C7B—H7BA109.5H19H—C19C—H19I109.5
C6A—C1A—C2A—C3A0.43 (16)C8B—O2B—C4B—C3B79.16 (14)
C11A—C1A—C2A—C3A177.91 (10)C8B—O2B—C4B—C5B104.32 (12)
C6A—C1A—C2A—Cl1A177.38 (8)O1B—C3B—C4B—O2B3.90 (16)
C11A—C1A—C2A—Cl1A4.27 (15)C2B—C3B—C4B—O2B177.06 (9)
C7A—O1A—C3A—C4A89.70 (15)O1B—C3B—C4B—C5B179.58 (9)
C7A—O1A—C3A—C2A94.67 (14)C2B—C3B—C4B—C5B0.54 (16)
C1A—C2A—C3A—O1A176.11 (10)C10B—O3B—C5B—C6B0.54 (16)
Cl1A—C2A—C3A—O1A6.00 (14)C10B—O3B—C5B—C4B179.34 (10)
C1A—C2A—C3A—C4A0.48 (16)O2B—C4B—C5B—O3B0.86 (15)
Cl1A—C2A—C3A—C4A178.36 (9)C3B—C4B—C5B—O3B177.39 (10)
C8A—O2A—C4A—C3A124.66 (15)O2B—C4B—C5B—C6B179.03 (10)
C8A—O2A—C4A—C5A58.83 (18)C3B—C4B—C5B—C6B2.50 (16)
O1A—C3A—C4A—O2A0.97 (16)O3B—C5B—C6B—C1B177.06 (10)
C2A—C3A—C4A—O2A176.61 (10)C4B—C5B—C6B—C1B2.82 (15)
O1A—C3A—C4A—C5A175.67 (10)C2B—C1B—C6B—C5B1.17 (15)
C2A—C3A—C4A—C5A0.03 (17)C11B—C1B—C6B—C5B177.57 (9)
C10A—O3A—C5A—C6A3.11 (19)C4B—O2B—C8B—C9B67.92 (16)
C10A—O3A—C5A—C4A178.00 (13)C2B—C1B—C11B—O4B122.81 (13)
O2A—C4A—C5A—O3A1.15 (17)C6B—C1B—C11B—O4B53.44 (14)
C3A—C4A—C5A—O3A177.60 (10)C2B—C1B—C11B—N1B58.5 (6)
O2A—C4A—C5A—C6A177.78 (10)C6B—C1B—C11B—N1B125.2 (6)
C3A—C4A—C5A—C6A1.34 (17)C2B—C1B—C11B—N1C59.4 (5)
O3A—C5A—C6A—C1A176.57 (11)C6B—C1B—C11B—N1C124.3 (5)
C4A—C5A—C6A—C1A2.27 (17)O4B—C11B—N1B—C12B7.2 (16)
C2A—C1A—C6A—C5A1.81 (16)C1B—C11B—N1B—C12B174.2 (11)
C11A—C1A—C6A—C5A176.67 (10)C11B—N1B—C12B—C13B0 (2)
C4A—O2A—C8A—C9A148.77 (16)C11B—N1B—C12B—C17B169.0 (10)
C12A—N1A—C11A—O4A2.59 (18)N1B—C12B—C13B—C14B175.2 (12)
C12A—N1A—C11A—C1A174.03 (10)C17B—C12B—C13B—C14B7.6 (18)
C2A—C1A—C11A—O4A129.47 (12)C12B—C13B—C14B—O5B173.3 (12)
C6A—C1A—C11A—O4A52.13 (15)C12B—C13B—C14B—C15B8.2 (15)
C2A—C1A—C11A—N1A53.79 (14)O5B—C14B—C15B—C16B148.7 (9)
C6A—C1A—C11A—N1A124.61 (10)C13B—C14B—C15B—C16B32.8 (11)
C11A—N1A—C12A—C13A9.78 (18)C14B—C15B—C16B—C19B172.5 (5)
C11A—N1A—C12A—C17A170.04 (11)C14B—C15B—C16B—C18B66.9 (6)
N1A—C12A—C13A—C14A176.55 (10)C14B—C15B—C16B—C17B53.5 (7)
C17A—C12A—C13A—C14A3.65 (17)C19B—C16B—C17B—C12B170.7 (7)
C12A—C13A—C14A—O5A173.40 (12)C18B—C16B—C17B—C12B68.9 (7)
C12A—C13A—C14A—C15A8.11 (17)C15B—C16B—C17B—C12B51.5 (7)
O5A—C14A—C15A—C16A146.37 (12)C13B—C12B—C17B—C16B31.0 (15)
C13A—C14A—C15A—C16A35.13 (16)N1B—C12B—C17B—C16B160.4 (9)
C14A—C15A—C16A—C19A65.22 (14)O4B—C11B—N1C—C12C9.7 (15)
C14A—C15A—C16A—C18A173.01 (13)C1B—C11B—N1C—C12C172.7 (11)
C14A—C15A—C16A—C17A54.92 (14)C11B—N1C—C12C—C13C8 (3)
C13A—C12A—C17A—C16A26.27 (17)C11B—N1C—C12C—C17C155.4 (10)
N1A—C12A—C17A—C16A153.90 (11)N1C—C12C—C13C—C14C176.1 (15)
C19A—C16A—C17A—C12A70.04 (15)C17C—C12C—C13C—C14C13 (2)
C18A—C16A—C17A—C12A168.10 (14)C12C—C13C—C14C—O5C171.1 (16)
C15A—C16A—C17A—C12A50.11 (15)C12C—C13C—C14C—C15C11 (2)
C6B—C1B—C2B—C3B0.81 (14)O5C—C14C—C15C—C16C151.4 (13)
C11B—C1B—C2B—C3B175.34 (9)C13C—C14C—C15C—C16C30.3 (14)
C6B—C1B—C2B—Cl1B178.96 (8)C14C—C15C—C16C—C17C51.9 (9)
C11B—C1B—C2B—Cl1B2.82 (14)C14C—C15C—C16C—C19C69.1 (9)
C7B—O1B—C3B—C4B79.27 (13)C14C—C15C—C16C—C18C170.8 (7)
C7B—O1B—C3B—C2B101.69 (13)C13C—C12C—C17C—C16C35.8 (17)
C1B—C2B—C3B—O1B177.93 (9)N1C—C12C—C17C—C16C158.7 (11)
Cl1B—C2B—C3B—O1B0.30 (14)C15C—C16C—C17C—C12C53.9 (10)
C1B—C2B—C3B—C4B1.12 (15)C19C—C16C—C17C—C12C67.5 (9)
Cl1B—C2B—C3B—C4B179.34 (8)C18C—C16C—C17C—C12C173.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O5B0.853 (16)2.040 (18)2.849 (8)158.1 (15)
N1A—H1AA···O5C0.853 (16)2.081 (19)2.909 (9)163.5 (15)
C7A—H7AA···O2Bi0.982.443.3451 (17)153
C8A—H8AB···Cl1Aii0.992.923.703 (2)137
C17A—H17A···O5B0.992.423.285 (7)146
C17A—H17A···O5C0.992.633.481 (8)144
C10B—H10F···O4Aiii0.982.463.4013 (15)161
N1B—H1BA···O5Aiv0.77 (5)2.31 (5)2.985 (10)147 (5)
N1C—H1CA···O5Aiv0.88 (5)1.96 (4)2.795 (12)159 (4)
C17C—H17E···O5Aiv0.992.543.364 (3)141
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+2, z+1; (iii) x+1, y+2, z+1; (iv) x, y+3/2, z1/2.
 

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