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In the title compound, C22H26ClNO5, there are two independent mol­ecules in the asymmetric unit. The mol­ecules are connected by C—H...O inter­actions into one-dimensional chains running in the b-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049555/kj2032sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049555/kj2032Isup2.hkl
Contains datablock I

CCDC reference: 630037

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.066
  • wR factor = 0.173
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C44 H52 Cl2 N2 O10 Atom count from _chemical_formula_moiety:C22 H26 Cl1 N1 O5 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-Chloroacetyl-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline top
Crystal data top
C22H26ClNO5F(000) = 1776
Mr = 419.89Dx = 1.339 Mg m3
Monoclinic, P21/nMelting point: 399(2) K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 16.380 (3) ÅCell parameters from 25 reflections
b = 15.396 (3) Åθ = 10–13°
c = 16.536 (3) ŵ = 0.22 mm1
β = 92.24 (3)°T = 293 K
V = 4167.0 (14) Å3Block, colourless
Z = 80.40 × 0.40 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
4379 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω/2θ scansh = 020
Absorption correction: ψ scan
(North et al., 1968)
k = 018
Tmin = 0.918, Tmax = 0.958l = 2020
8446 measured reflections3 standard reflections every 200 reflections
8155 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.173 w = 1/[σ2(Fo2) + (0.07P)2 + 1.23P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
8155 reflectionsΔρmax = 0.26 e Å3
524 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (5)
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.24271 (7)0.68469 (8)0.19169 (8)0.0877 (4)
O10.40172 (16)0.95490 (15)0.42181 (18)0.0705 (8)
O20.53271 (15)0.90412 (14)0.35446 (17)0.0592 (7)
O30.54951 (14)0.19205 (14)0.34776 (15)0.0531 (7)
O40.64440 (13)0.31732 (14)0.31061 (15)0.0487 (6)
O50.21620 (16)0.5896 (2)0.3395 (2)0.0852 (10)
N10.34404 (16)0.54171 (17)0.36854 (17)0.0412 (7)
C10.3381 (3)0.9881 (3)0.4683 (3)0.0854 (15)
H1A0.33531.05000.46190.128*
H1B0.34870.97420.52430.128*
H1C0.28710.96270.45010.128*
C20.6068 (2)0.8789 (2)0.3195 (3)0.0610 (11)
H2A0.63430.92940.30020.091*
H2B0.59510.84000.27510.091*
H2C0.64120.85010.35950.091*
C30.4859 (2)0.8396 (2)0.3856 (2)0.0424 (8)
C40.50551 (19)0.7521 (2)0.3839 (2)0.0399 (8)
H4A0.55220.73410.35830.048*
C50.4560 (2)0.6905 (2)0.4202 (2)0.0403 (8)
C60.3872 (2)0.7191 (2)0.4574 (2)0.0464 (9)
H6A0.35370.67910.48210.056*
C70.3672 (2)0.8067 (2)0.4586 (2)0.0489 (9)
H7A0.32020.82450.48390.059*
C80.4156 (2)0.8677 (2)0.4230 (2)0.0462 (9)
C90.4798 (2)0.59601 (19)0.4200 (2)0.0435 (8)
H9A0.47180.57240.47350.052*
H9B0.53760.59200.40980.052*
C100.43226 (18)0.53877 (19)0.35722 (19)0.0365 (8)
H10A0.44240.56160.30320.044*
C110.3172 (2)0.4907 (2)0.4367 (2)0.0519 (10)
H11A0.25960.50120.44440.062*
H11B0.34740.50830.48560.062*
C120.3310 (2)0.3948 (2)0.4216 (2)0.0485 (9)
H12A0.32650.36320.47190.058*
H12B0.28900.37350.38370.058*
C130.41365 (19)0.3779 (2)0.38803 (19)0.0378 (8)
C140.4427 (2)0.2922 (2)0.3849 (2)0.0401 (8)
H14A0.40990.24710.40230.048*
C150.5181 (2)0.2735 (2)0.3568 (2)0.0393 (8)
C160.56884 (19)0.3418 (2)0.33407 (19)0.0357 (8)
C170.54007 (18)0.4261 (2)0.33493 (18)0.0356 (8)
H17A0.57340.47100.31820.043*
C180.46174 (18)0.44490 (19)0.36050 (18)0.0342 (7)
C190.6980 (2)0.3838 (2)0.2865 (2)0.0552 (10)
H19A0.74880.35850.27140.083*
H19B0.70790.42340.33060.083*
H19C0.67370.41450.24110.083*
C200.4975 (3)0.1202 (2)0.3656 (3)0.0735 (13)
H20A0.52620.06680.35710.110*
H20B0.44940.12210.33070.110*
H20C0.48230.12360.42100.110*
C210.2883 (2)0.5873 (2)0.3239 (2)0.0494 (9)
C220.3210 (2)0.6370 (2)0.2528 (2)0.0537 (10)
H22A0.35210.59770.22000.064*
H22B0.35770.68220.27300.064*
Cl20.27754 (8)0.59172 (8)0.20884 (8)0.0931 (5)
O60.10387 (14)0.30533 (14)0.40113 (15)0.0514 (6)
O70.02825 (14)0.36487 (14)0.33959 (16)0.0535 (7)
O80.14145 (13)0.94120 (14)0.33332 (15)0.0501 (6)
O90.05266 (14)1.06827 (13)0.37901 (15)0.0492 (6)
O100.29576 (15)0.67920 (19)0.3619 (2)0.0796 (9)
N20.16624 (16)0.72515 (16)0.38667 (17)0.0413 (7)
C230.1691 (2)0.2694 (2)0.4447 (2)0.0600 (11)
H23A0.17220.20800.43500.090*
H23B0.21960.29620.42690.090*
H23C0.15950.27990.50150.090*
C240.1012 (2)0.3949 (3)0.3051 (3)0.0652 (12)
H24A0.13000.34650.28310.098*
H24B0.13510.42260.34610.098*
H24C0.08780.43570.26270.098*
C250.02070 (19)0.4252 (2)0.3739 (2)0.0374 (8)
C260.00278 (19)0.5132 (2)0.37955 (19)0.0380 (8)
H26A0.04350.53460.35550.046*
C270.05300 (19)0.57003 (19)0.42074 (19)0.0370 (8)
C280.1213 (2)0.5365 (2)0.4545 (2)0.0436 (8)
H28A0.15520.57330.48260.052*
C290.1411 (2)0.4490 (2)0.4479 (2)0.0420 (8)
H29A0.18840.42810.47040.050*
C300.09097 (19)0.3934 (2)0.40816 (19)0.0367 (8)
C310.0301 (2)0.66468 (19)0.4292 (2)0.0420 (8)
H31A0.02760.67080.41910.050*
H31B0.03790.68240.48460.050*
C320.07867 (18)0.72711 (19)0.37233 (19)0.0348 (7)
H32A0.07120.70790.31660.042*
C330.1897 (2)0.7757 (2)0.4577 (2)0.0510 (9)
H33A0.15840.75590.50520.061*
H33B0.24720.76660.46700.061*
C340.1740 (2)0.8712 (2)0.4445 (2)0.0460 (9)
H34A0.21610.89460.40780.055*
H34B0.17690.90170.49560.055*
C350.09184 (18)0.88676 (19)0.41002 (19)0.0348 (7)
C360.05933 (19)0.9712 (2)0.40980 (19)0.0376 (8)
H36A0.09051.01690.42860.045*
C370.01732 (19)0.98791 (19)0.38258 (19)0.0362 (8)
C380.06527 (18)0.9182 (2)0.35644 (19)0.0360 (8)
C390.03330 (18)0.83571 (19)0.35413 (18)0.0340 (7)
H39A0.06450.79010.33520.041*
C400.04604 (18)0.81943 (19)0.37996 (18)0.0319 (7)
C410.0011 (2)1.1422 (2)0.3906 (2)0.0555 (10)
H41A0.03281.19450.38690.083*
H41B0.02201.13900.44300.083*
H41C0.04211.14280.34960.083*
C420.1928 (2)0.8735 (2)0.3077 (2)0.0588 (11)
H42A0.24430.89730.29290.088*
H42B0.16740.84460.26180.088*
H42C0.20150.83260.35100.088*
C430.2246 (2)0.6806 (2)0.3439 (2)0.0486 (9)
C440.1952 (2)0.6321 (2)0.2701 (2)0.0582 (11)
H44A0.16060.58410.28790.070*
H44B0.16260.67100.23830.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0862 (8)0.0801 (8)0.0942 (9)0.0308 (7)0.0291 (7)0.0063 (7)
O10.0770 (19)0.0294 (14)0.108 (2)0.0110 (13)0.0360 (17)0.0053 (14)
O20.0571 (16)0.0330 (14)0.089 (2)0.0017 (12)0.0240 (15)0.0025 (13)
O30.0613 (16)0.0270 (13)0.0715 (18)0.0024 (12)0.0102 (13)0.0003 (12)
O40.0421 (14)0.0365 (13)0.0683 (17)0.0027 (11)0.0122 (12)0.0007 (12)
O50.0436 (17)0.094 (2)0.119 (3)0.0132 (16)0.0143 (17)0.014 (2)
N10.0404 (16)0.0347 (16)0.0493 (18)0.0009 (13)0.0098 (13)0.0014 (13)
C10.087 (3)0.045 (3)0.127 (4)0.016 (2)0.038 (3)0.022 (3)
C20.047 (2)0.048 (2)0.089 (3)0.0020 (18)0.018 (2)0.008 (2)
C30.045 (2)0.0303 (19)0.052 (2)0.0041 (16)0.0085 (17)0.0017 (16)
C40.0392 (19)0.0338 (19)0.047 (2)0.0027 (15)0.0037 (16)0.0076 (16)
C50.046 (2)0.0341 (19)0.041 (2)0.0011 (16)0.0032 (16)0.0010 (16)
C60.057 (2)0.0325 (19)0.050 (2)0.0079 (17)0.0086 (18)0.0013 (16)
C70.048 (2)0.046 (2)0.053 (2)0.0012 (18)0.0149 (18)0.0103 (18)
C80.052 (2)0.0322 (19)0.055 (2)0.0021 (17)0.0085 (18)0.0052 (17)
C90.050 (2)0.0275 (18)0.052 (2)0.0016 (16)0.0027 (17)0.0001 (16)
C100.0416 (19)0.0280 (17)0.0401 (19)0.0002 (14)0.0054 (15)0.0017 (15)
C110.053 (2)0.046 (2)0.059 (2)0.0043 (18)0.0240 (19)0.0045 (19)
C120.052 (2)0.036 (2)0.059 (2)0.0053 (17)0.0188 (18)0.0011 (18)
C130.0416 (19)0.0309 (18)0.041 (2)0.0054 (15)0.0064 (15)0.0033 (15)
C140.048 (2)0.0295 (18)0.043 (2)0.0086 (15)0.0058 (16)0.0017 (15)
C150.047 (2)0.0262 (18)0.044 (2)0.0003 (15)0.0026 (16)0.0004 (15)
C160.0371 (18)0.0319 (18)0.0382 (19)0.0009 (15)0.0013 (15)0.0009 (15)
C170.0375 (18)0.0324 (18)0.0367 (19)0.0069 (14)0.0001 (15)0.0039 (15)
C180.0368 (18)0.0294 (17)0.0363 (18)0.0022 (14)0.0012 (14)0.0021 (14)
C190.039 (2)0.058 (2)0.069 (3)0.0037 (18)0.0071 (19)0.001 (2)
C200.086 (3)0.025 (2)0.109 (4)0.003 (2)0.012 (3)0.004 (2)
C210.042 (2)0.038 (2)0.069 (3)0.0031 (17)0.0066 (19)0.0069 (19)
C220.052 (2)0.050 (2)0.059 (2)0.0146 (18)0.0075 (19)0.0023 (19)
Cl20.0990 (9)0.0782 (8)0.0984 (10)0.0345 (7)0.0454 (8)0.0071 (7)
O60.0522 (15)0.0304 (13)0.0728 (18)0.0094 (11)0.0179 (13)0.0037 (12)
O70.0485 (15)0.0371 (14)0.0765 (18)0.0022 (11)0.0225 (13)0.0065 (13)
O80.0403 (14)0.0387 (14)0.0723 (18)0.0044 (11)0.0159 (12)0.0052 (12)
O90.0537 (15)0.0246 (12)0.0701 (17)0.0042 (11)0.0138 (13)0.0037 (11)
O100.0382 (16)0.082 (2)0.119 (3)0.0112 (15)0.0057 (16)0.0056 (19)
N20.0415 (16)0.0312 (15)0.0517 (18)0.0042 (13)0.0067 (14)0.0016 (13)
C230.056 (2)0.038 (2)0.087 (3)0.0111 (18)0.016 (2)0.006 (2)
C240.043 (2)0.065 (3)0.090 (3)0.000 (2)0.029 (2)0.013 (2)
C250.0384 (19)0.0326 (18)0.041 (2)0.0047 (15)0.0029 (15)0.0005 (15)
C260.0364 (18)0.0318 (19)0.046 (2)0.0019 (15)0.0016 (15)0.0066 (15)
C270.0409 (19)0.0289 (17)0.0408 (19)0.0023 (15)0.0047 (15)0.0058 (15)
C280.050 (2)0.0357 (19)0.046 (2)0.0071 (17)0.0123 (17)0.0010 (16)
C290.048 (2)0.0332 (19)0.045 (2)0.0038 (16)0.0117 (16)0.0042 (16)
C300.0433 (19)0.0264 (17)0.0409 (19)0.0013 (15)0.0050 (16)0.0029 (15)
C310.051 (2)0.0300 (18)0.045 (2)0.0003 (16)0.0037 (17)0.0001 (16)
C320.0366 (18)0.0285 (17)0.0394 (19)0.0028 (14)0.0013 (15)0.0006 (14)
C330.048 (2)0.045 (2)0.061 (2)0.0005 (17)0.0179 (18)0.0031 (19)
C340.044 (2)0.039 (2)0.056 (2)0.0003 (16)0.0119 (17)0.0044 (17)
C350.0375 (18)0.0302 (18)0.0368 (19)0.0017 (14)0.0035 (15)0.0007 (14)
C360.0405 (19)0.0283 (17)0.044 (2)0.0047 (15)0.0063 (16)0.0044 (15)
C370.0421 (19)0.0283 (18)0.0381 (19)0.0034 (15)0.0017 (15)0.0027 (15)
C380.0325 (17)0.0366 (19)0.0392 (19)0.0022 (15)0.0034 (15)0.0008 (15)
C390.0349 (18)0.0275 (17)0.0395 (19)0.0036 (14)0.0025 (15)0.0022 (14)
C400.0344 (17)0.0281 (17)0.0332 (18)0.0002 (14)0.0011 (14)0.0013 (14)
C410.066 (3)0.0253 (19)0.076 (3)0.0023 (17)0.008 (2)0.0033 (18)
C420.040 (2)0.057 (2)0.080 (3)0.0031 (18)0.017 (2)0.006 (2)
C430.041 (2)0.0319 (19)0.072 (3)0.0062 (16)0.0041 (19)0.0124 (18)
C440.061 (2)0.046 (2)0.066 (3)0.0180 (19)0.014 (2)0.005 (2)
Geometric parameters (Å, º) top
Cl1—C221.761 (3)Cl2—C441.768 (4)
O1—C81.362 (4)O6—C301.376 (4)
O1—C11.414 (4)O6—C231.423 (4)
O2—C31.368 (4)O7—C251.365 (4)
O2—C21.419 (4)O7—C241.422 (4)
O3—C151.366 (4)O8—C381.366 (4)
O3—C201.433 (4)O8—C421.415 (4)
O4—C161.365 (4)O9—C371.368 (3)
O4—C191.416 (4)O9—C411.435 (4)
O5—C211.219 (4)O10—C431.215 (4)
N1—C211.348 (4)N2—C431.353 (4)
N1—C111.456 (4)N2—C321.463 (4)
N1—C101.465 (4)N2—C331.472 (4)
C1—H1A0.9600C23—H23A0.9600
C1—H1B0.9600C23—H23B0.9600
C1—H1C0.9600C23—H23C0.9600
C2—H2A0.9600C24—H24A0.9600
C2—H2B0.9600C24—H24B0.9600
C2—H2C0.9600C24—H24C0.9600
C3—C41.386 (4)C25—C261.388 (4)
C3—C81.396 (4)C25—C301.392 (4)
C4—C51.399 (4)C26—C271.397 (4)
C4—H4A0.9300C26—H26A0.9300
C5—C61.377 (4)C27—C281.370 (4)
C5—C91.506 (4)C27—C311.510 (4)
C6—C71.389 (4)C28—C291.390 (4)
C6—H6A0.9300C28—H28A0.9300
C7—C81.377 (4)C29—C301.371 (4)
C7—H7A0.9300C29—H29A0.9300
C9—C101.548 (4)C31—C321.543 (4)
C9—H9A0.9700C31—H31A0.9700
C9—H9B0.9700C31—H31B0.9700
C10—C181.524 (4)C32—C401.522 (4)
C10—H10A0.9800C32—H32A0.9800
C11—C121.515 (4)C33—C341.511 (5)
C11—H11A0.9700C33—H33A0.9700
C11—H11B0.9700C33—H33B0.9700
C12—C131.505 (4)C34—C351.501 (4)
C12—H12A0.9700C34—H34A0.9700
C12—H12B0.9700C34—H34B0.9700
C13—C181.385 (4)C35—C401.383 (4)
C13—C141.405 (4)C35—C361.404 (4)
C14—C151.368 (4)C36—C371.375 (4)
C14—H14A0.9300C36—H36A0.9300
C15—C161.400 (4)C37—C381.408 (4)
C16—C171.380 (4)C38—C391.373 (4)
C17—C181.397 (4)C39—C401.406 (4)
C17—H17A0.9300C39—H39A0.9300
C19—H19A0.9600C41—H41A0.9600
C19—H19B0.9600C41—H41B0.9600
C19—H19C0.9600C41—H41C0.9600
C20—H20A0.9600C42—H42A0.9600
C20—H20B0.9600C42—H42B0.9600
C20—H20C0.9600C42—H42C0.9600
C21—C221.518 (5)C43—C441.525 (5)
C22—H22A0.9700C44—H44A0.9700
C22—H22B0.9700C44—H44B0.9700
C8—O1—C1118.4 (3)C30—O6—C23117.1 (3)
C3—O2—C2117.1 (3)C25—O7—C24117.6 (3)
C15—O3—C20117.2 (3)C38—O8—C42116.9 (3)
C16—O4—C19117.4 (2)C37—O9—C41117.4 (2)
C21—N1—C11119.1 (3)C43—N2—C32127.1 (3)
C21—N1—C10126.6 (3)C43—N2—C33118.9 (3)
C11—N1—C10114.3 (3)C32—N2—C33114.0 (3)
O1—C1—H1A109.5O6—C23—H23A109.5
O1—C1—H1B109.5O6—C23—H23B109.5
H1A—C1—H1B109.5H23A—C23—H23B109.5
O1—C1—H1C109.5O6—C23—H23C109.5
H1A—C1—H1C109.5H23A—C23—H23C109.5
H1B—C1—H1C109.5H23B—C23—H23C109.5
O2—C2—H2A109.5O7—C24—H24A109.5
O2—C2—H2B109.5O7—C24—H24B109.5
H2A—C2—H2B109.5H24A—C24—H24B109.5
O2—C2—H2C109.5O7—C24—H24C109.5
H2A—C2—H2C109.5H24A—C24—H24C109.5
H2B—C2—H2C109.5H24B—C24—H24C109.5
O2—C3—C4124.3 (3)O7—C25—C26124.4 (3)
O2—C3—C8115.2 (3)O7—C25—C30116.0 (3)
C4—C3—C8120.4 (3)C26—C25—C30119.5 (3)
C3—C4—C5120.8 (3)C25—C26—C27121.1 (3)
C3—C4—H4A119.6C25—C26—H26A119.4
C5—C4—H4A119.6C27—C26—H26A119.4
C6—C5—C4118.3 (3)C28—C27—C26117.9 (3)
C6—C5—C9121.8 (3)C28—C27—C31122.0 (3)
C4—C5—C9120.0 (3)C26—C27—C31120.1 (3)
C5—C6—C7121.0 (3)C27—C28—C29121.7 (3)
C5—C6—H6A119.5C27—C28—H28A119.2
C7—C6—H6A119.5C29—C28—H28A119.2
C8—C7—C6121.0 (3)C30—C29—C28120.0 (3)
C8—C7—H7A119.5C30—C29—H29A120.0
C6—C7—H7A119.5C28—C29—H29A120.0
O1—C8—C7125.4 (3)C29—C30—O6124.2 (3)
O1—C8—C3116.1 (3)C29—C30—C25119.7 (3)
C7—C8—C3118.5 (3)O6—C30—C25116.1 (3)
C5—C9—C10115.4 (3)C27—C31—C32115.1 (3)
C5—C9—H9A108.4C27—C31—H31A108.5
C10—C9—H9A108.4C32—C31—H31A108.5
C5—C9—H9B108.4C27—C31—H31B108.5
C10—C9—H9B108.4C32—C31—H31B108.5
H9A—C9—H9B107.5H31A—C31—H31B107.5
N1—C10—C18109.7 (2)N2—C32—C40110.4 (2)
N1—C10—C9111.7 (3)N2—C32—C31111.9 (3)
C18—C10—C9111.5 (2)C40—C32—C31111.1 (2)
N1—C10—H10A108.0N2—C32—H32A107.7
C18—C10—H10A108.0C40—C32—H32A107.7
C9—C10—H10A108.0C31—C32—H32A107.7
N1—C11—C12110.3 (3)N2—C33—C34110.4 (3)
N1—C11—H11A109.6N2—C33—H33A109.6
C12—C11—H11A109.6C34—C33—H33A109.6
N1—C11—H11B109.6N2—C33—H33B109.6
C12—C11—H11B109.6C34—C33—H33B109.6
H11A—C11—H11B108.1H33A—C33—H33B108.1
C13—C12—C11111.8 (3)C35—C34—C33111.7 (3)
C13—C12—H12A109.3C35—C34—H34A109.3
C11—C12—H12A109.3C33—C34—H34A109.3
C13—C12—H12B109.3C35—C34—H34B109.3
C11—C12—H12B109.3C33—C34—H34B109.3
H12A—C12—H12B107.9H34A—C34—H34B107.9
C18—C13—C14119.3 (3)C40—C35—C36118.8 (3)
C18—C13—C12121.6 (3)C40—C35—C34121.6 (3)
C14—C13—C12119.1 (3)C36—C35—C34119.6 (3)
C15—C14—C13121.4 (3)C37—C36—C35121.7 (3)
C15—C14—H14A119.3C37—C36—H36A119.1
C13—C14—H14A119.3C35—C36—H36A119.1
O3—C15—C14125.4 (3)O9—C37—C36125.3 (3)
O3—C15—C16115.5 (3)O9—C37—C38115.7 (3)
C14—C15—C16119.1 (3)C36—C37—C38119.0 (3)
O4—C16—C17125.2 (3)O8—C38—C39125.7 (3)
O4—C16—C15115.0 (3)O8—C38—C37114.5 (3)
C17—C16—C15119.8 (3)C39—C38—C37119.8 (3)
C16—C17—C18121.1 (3)C38—C39—C40120.8 (3)
C16—C17—H17A119.5C38—C39—H39A119.6
C18—C17—H17A119.5C40—C39—H39A119.6
C13—C18—C17119.1 (3)C35—C40—C39119.7 (3)
C13—C18—C10122.3 (3)C35—C40—C32122.4 (3)
C17—C18—C10118.6 (3)C39—C40—C32117.8 (3)
O4—C19—H19A109.5O9—C41—H41A109.5
O4—C19—H19B109.5O9—C41—H41B109.5
H19A—C19—H19B109.5H41A—C41—H41B109.5
O4—C19—H19C109.5O9—C41—H41C109.5
H19A—C19—H19C109.5H41A—C41—H41C109.5
H19B—C19—H19C109.5H41B—C41—H41C109.5
O3—C20—H20A109.5O8—C42—H42A109.5
O3—C20—H20B109.5O8—C42—H42B109.5
H20A—C20—H20B109.5H42A—C42—H42B109.5
O3—C20—H20C109.5O8—C42—H42C109.5
H20A—C20—H20C109.5H42A—C42—H42C109.5
H20B—C20—H20C109.5H42B—C42—H42C109.5
O5—C21—N1122.7 (4)O10—C43—N2123.1 (4)
O5—C21—C22121.5 (4)O10—C43—C44121.6 (3)
N1—C21—C22115.8 (3)N2—C43—C44115.3 (3)
C21—C22—Cl1112.6 (3)C43—C44—Cl2111.9 (3)
C21—C22—H22A109.1C43—C44—H44A109.2
Cl1—C22—H22A109.1Cl2—C44—H44A109.2
C21—C22—H22B109.1C43—C44—H44B109.2
Cl1—C22—H22B109.1Cl2—C44—H44B109.2
H22A—C22—H22B107.8H44A—C44—H44B107.9
C2—O2—C3—C41.1 (5)C24—O7—C25—C262.0 (5)
C2—O2—C3—C8176.9 (3)C24—O7—C25—C30179.1 (3)
O2—C3—C4—C5177.3 (3)O7—C25—C26—C27175.3 (3)
C8—C3—C4—C50.7 (5)C30—C25—C26—C271.6 (5)
C3—C4—C5—C60.2 (5)C25—C26—C27—C280.9 (5)
C3—C4—C5—C9178.1 (3)C25—C26—C27—C31177.3 (3)
C4—C5—C6—C70.3 (5)C26—C27—C28—C290.6 (5)
C9—C5—C6—C7178.5 (3)C31—C27—C28—C29178.7 (3)
C5—C6—C7—C80.3 (5)C27—C28—C29—C301.4 (5)
C1—O1—C8—C77.7 (6)C28—C29—C30—O6177.5 (3)
C1—O1—C8—C3171.3 (4)C28—C29—C30—C250.6 (5)
C6—C7—C8—O1179.2 (3)C23—O6—C30—C296.3 (5)
C6—C7—C8—C30.2 (5)C23—O6—C30—C25171.9 (3)
O2—C3—C8—O11.7 (5)O7—C25—C30—C29176.4 (3)
C4—C3—C8—O1179.8 (3)C26—C25—C30—C290.8 (5)
O2—C3—C8—C7177.5 (3)O7—C25—C30—O61.9 (4)
C4—C3—C8—C70.6 (5)C26—C25—C30—O6179.1 (3)
C6—C5—C9—C1079.3 (4)C28—C27—C31—C3278.6 (4)
C4—C5—C9—C10102.5 (4)C26—C27—C31—C32103.3 (3)
C21—N1—C10—C18133.4 (3)C43—N2—C32—C40136.8 (3)
C11—N1—C10—C1848.1 (3)C33—N2—C32—C4045.5 (3)
C21—N1—C10—C9102.5 (4)C43—N2—C32—C3198.9 (4)
C11—N1—C10—C976.0 (3)C33—N2—C32—C3178.8 (3)
C5—C9—C10—N158.0 (4)C27—C31—C32—N261.2 (4)
C5—C9—C10—C18178.9 (3)C27—C31—C32—C40174.9 (3)
C21—N1—C11—C12115.3 (3)C43—N2—C33—C34116.8 (3)
C10—N1—C11—C1266.0 (4)C32—N2—C33—C3465.3 (4)
N1—C11—C12—C1344.3 (4)N2—C33—C34—C3545.2 (4)
C11—C12—C13—C1811.8 (5)C33—C34—C35—C4012.0 (4)
C11—C12—C13—C14168.0 (3)C33—C34—C35—C36166.5 (3)
C18—C13—C14—C151.4 (5)C40—C35—C36—C371.7 (5)
C12—C13—C14—C15178.4 (3)C34—C35—C36—C37176.7 (3)
C20—O3—C15—C143.1 (5)C41—O9—C37—C3611.8 (5)
C20—O3—C15—C16176.2 (3)C41—O9—C37—C38168.7 (3)
C13—C14—C15—O3176.5 (3)C35—C36—C37—O9178.7 (3)
C13—C14—C15—C162.9 (5)C35—C36—C37—C381.9 (5)
C19—O4—C16—C171.1 (5)C42—O8—C38—C392.6 (5)
C19—O4—C16—C15179.6 (3)C42—O8—C38—C37179.0 (3)
O3—C15—C16—O43.7 (4)O9—C37—C38—O81.7 (4)
C14—C15—C16—O4176.9 (3)C36—C37—C38—O8177.8 (3)
O3—C15—C16—C17174.9 (3)O9—C37—C38—C39176.8 (3)
C14—C15—C16—C174.5 (5)C36—C37—C38—C393.7 (5)
O4—C16—C17—C18179.6 (3)O8—C38—C39—C40179.7 (3)
C15—C16—C17—C182.0 (5)C37—C38—C39—C402.0 (5)
C14—C13—C18—C173.9 (5)C36—C35—C40—C393.5 (4)
C12—C13—C18—C17175.9 (3)C34—C35—C40—C39175.0 (3)
C14—C13—C18—C10176.2 (3)C36—C35—C40—C32175.6 (3)
C12—C13—C18—C104.0 (5)C34—C35—C40—C325.9 (5)
C16—C17—C18—C132.3 (5)C38—C39—C40—C351.6 (5)
C16—C17—C18—C10177.8 (3)C38—C39—C40—C32177.5 (3)
N1—C10—C18—C1312.9 (4)N2—C32—C40—C3510.2 (4)
C9—C10—C18—C13111.3 (3)C31—C32—C40—C35114.7 (3)
N1—C10—C18—C17167.2 (3)N2—C32—C40—C39168.9 (3)
C9—C10—C18—C1768.6 (4)C31—C32—C40—C3966.2 (4)
C11—N1—C21—O52.0 (5)C32—N2—C43—O10176.6 (3)
C10—N1—C21—O5176.5 (3)C33—N2—C43—O101.0 (5)
C11—N1—C21—C22178.6 (3)C32—N2—C43—C444.0 (5)
C10—N1—C21—C222.9 (5)C33—N2—C43—C44178.5 (3)
O5—C21—C22—Cl17.1 (5)O10—C43—C44—Cl29.6 (5)
N1—C21—C22—Cl1173.4 (2)N2—C43—C44—Cl2169.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20A···O2i0.962.513.383 (4)152
C22—H22A···O8ii0.972.573.400 (4)144
C22—H22A···O9ii0.972.353.241 (4)153
C44—H44B···O3iii0.972.403.272 (4)149
C44—H44B···O4iii0.972.423.270 (4)147
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2.
 

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