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In the title compound, C18H18ClN5O2, there are two independent mol­ecules in the asymmetric unit. In both mol­ecules, the pyrimidine ring is almost coplanar with the central pyrazole ring, while the benzene ring is almost perpendicular to it.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018629/fl2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018629/fl2024Isup2.hkl
Contains datablock I

CCDC reference: 610766

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.050
  • wR factor = 0.146
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker,1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

(E)-5-(3,5-Dimethylphenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde O-(2-chloropyrimidin-4-yl)oxime top
Crystal data top
C18H18ClN5O2Z = 4
Mr = 371.82F(000) = 776
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.217 (2) ÅCell parameters from 2954 reflections
b = 8.4391 (15) Åθ = 2.7–23.3°
c = 30.674 (5) ŵ = 0.23 mm1
α = 93.15 (1)°T = 294 K
β = 90.342 (3)°Block, colorless
γ = 118.958 (3)°0.50 × 0.30 × 0.20 mm
V = 1857.0 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
6481 independent reflections
Radiation source: fine-focus sealed tube4096 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 25.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.895, Tmax = 0.956k = 109
9445 measured reflectionsl = 3636
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0725P)2 + 0.178P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
6481 reflectionsΔρmax = 0.36 e Å3
478 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0153 (15)
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
Cl10.51047 (14)0.49841 (11)0.39047 (3)0.0877 (3)
Cl21.01971 (16)0.00577 (15)0.10191 (3)0.0924 (4)
O10.8097 (3)0.1268 (2)0.35789 (6)0.0572 (5)
O21.2226 (3)0.7954 (3)0.39136 (6)0.0516 (5)
O30.6676 (3)0.2922 (3)0.14041 (6)0.0600 (6)
O40.4006 (3)0.7109 (2)0.11986 (6)0.0596 (6)
N10.4050 (3)0.3894 (3)0.32449 (8)0.0561 (6)
N20.6599 (3)0.1664 (3)0.36949 (7)0.0501 (6)
N30.8081 (4)0.2701 (3)0.33422 (7)0.0546 (6)
N41.0988 (4)0.8888 (3)0.33576 (7)0.0527 (6)
N50.9751 (4)0.8205 (3)0.30058 (7)0.0567 (7)
N60.8249 (4)0.0782 (3)0.17097 (8)0.0590 (7)
N70.8242 (3)0.1444 (3)0.12630 (7)0.0512 (6)
N80.5251 (4)0.3016 (3)0.16579 (7)0.0548 (6)
N90.1872 (4)0.6013 (3)0.17538 (8)0.0566 (7)
N100.1335 (4)0.4805 (3)0.20755 (7)0.0575 (7)
C10.5267 (4)0.3321 (4)0.35717 (9)0.0509 (7)
C20.4193 (4)0.2547 (4)0.30039 (9)0.0569 (8)
H20.33690.28500.27660.068*
C30.5482 (4)0.0761 (4)0.30896 (8)0.0505 (7)
H30.55430.01490.29210.061*
C40.6689 (4)0.0399 (3)0.34433 (8)0.0438 (7)
C50.9364 (4)0.4201 (4)0.35133 (9)0.0491 (7)
H51.01020.41780.37410.059*
C60.9725 (4)0.5930 (3)0.33697 (8)0.0437 (7)
C70.8990 (4)0.6412 (4)0.30152 (8)0.0478 (7)
C80.7566 (5)0.5202 (4)0.26745 (10)0.0692 (9)
H8A0.73430.59260.24770.104*
H8B0.64290.44200.28110.104*
H8C0.80070.44820.25160.104*
C91.2091 (5)1.0839 (4)0.34618 (11)0.0743 (10)
H9A1.26461.10580.37500.111*
H9B1.13021.13820.34490.111*
H9C1.30521.13610.32550.111*
C101.0995 (4)0.7572 (3)0.35770 (8)0.0425 (6)
C111.1571 (4)0.7780 (3)0.43404 (8)0.0405 (6)
C121.2726 (4)0.7712 (3)0.46568 (8)0.0445 (7)
H121.38350.77430.45810.053*
C131.2223 (4)0.7597 (4)0.50890 (9)0.0472 (7)
C141.3464 (5)0.7530 (5)0.54446 (10)0.0671 (9)
H14A1.47180.80520.53490.101*
H14B1.30350.62900.55080.101*
H14C1.34250.82030.57030.101*
C151.0546 (4)0.7529 (4)0.51870 (9)0.0525 (7)
H151.01930.74350.54760.063*
C160.9380 (4)0.7595 (4)0.48698 (9)0.0494 (7)
C170.7566 (4)0.7526 (5)0.49872 (11)0.0700 (9)
H17A0.66060.62830.49900.105*
H17B0.72340.81260.47750.105*
H17C0.77030.81230.52710.105*
C180.9913 (4)0.7731 (3)0.44373 (8)0.0449 (7)
H180.91620.77880.42180.054*
C190.8722 (4)0.0238 (4)0.13744 (9)0.0510 (7)
C200.7119 (5)0.0473 (4)0.19779 (9)0.0623 (9)
H200.67480.11180.22280.075*
C210.6488 (4)0.0720 (4)0.19063 (9)0.0536 (8)
H210.56920.08860.20950.064*
C220.7111 (4)0.1665 (4)0.15354 (8)0.0452 (7)
C230.4959 (4)0.4246 (4)0.15097 (9)0.0510 (7)
H230.56670.48940.12820.061*
C240.3580 (4)0.4664 (4)0.16811 (8)0.0444 (7)
C250.2358 (4)0.3993 (4)0.20276 (8)0.0470 (7)
C260.2151 (5)0.2594 (4)0.23331 (9)0.0626 (9)
H26A0.11890.24120.25330.094*
H26B0.33050.29970.24940.094*
H26C0.18240.14720.21690.094*
C270.1006 (6)0.7148 (5)0.17064 (13)0.0889 (12)
H27A0.18540.82370.15730.133*
H27B0.07040.74570.19890.133*
H27C0.01090.64990.15260.133*
C280.3197 (4)0.5947 (4)0.15181 (8)0.0476 (7)
C290.3528 (4)0.6416 (3)0.07602 (8)0.0441 (7)
C300.4723 (4)0.7493 (4)0.04592 (9)0.0481 (7)
H300.57690.85810.05500.058*
C310.4361 (4)0.6951 (4)0.00190 (9)0.0481 (7)
C320.5628 (5)0.8117 (5)0.03216 (10)0.0700 (9)
H32A0.64360.93140.01920.105*
H32B0.48940.81870.05570.105*
H32C0.63630.75910.04330.105*
C330.2784 (4)0.5310 (4)0.01017 (9)0.0506 (7)
H330.25360.49290.03960.061*
C340.1568 (4)0.4221 (3)0.02006 (9)0.0462 (7)
C350.0120 (4)0.2462 (4)0.00598 (10)0.0631 (9)
H35A0.06760.26090.02000.095*
H35B0.10010.21070.02880.095*
H35C0.02340.15430.00020.095*
C360.1955 (4)0.4809 (3)0.06414 (9)0.0468 (7)
H360.11550.41220.08530.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0952 (8)0.0398 (5)0.1055 (7)0.0148 (5)0.0260 (6)0.0097 (4)
Cl20.1287 (9)0.1304 (9)0.0752 (6)0.1043 (8)0.0464 (6)0.0396 (6)
O10.0581 (13)0.0368 (11)0.0645 (12)0.0134 (10)0.0069 (10)0.0045 (9)
O20.0416 (11)0.0623 (12)0.0399 (10)0.0166 (10)0.0050 (9)0.0013 (9)
O30.0781 (15)0.0690 (14)0.0553 (12)0.0521 (13)0.0185 (11)0.0158 (10)
O40.0818 (16)0.0441 (11)0.0438 (11)0.0237 (11)0.0079 (11)0.0019 (9)
N10.0547 (16)0.0485 (14)0.0549 (15)0.0181 (13)0.0008 (13)0.0083 (12)
N20.0493 (15)0.0366 (13)0.0558 (14)0.0145 (12)0.0040 (12)0.0013 (11)
N30.0616 (17)0.0399 (14)0.0570 (15)0.0202 (13)0.0009 (13)0.0057 (11)
N40.0617 (17)0.0403 (13)0.0502 (14)0.0202 (13)0.0032 (12)0.0009 (11)
N50.0659 (18)0.0535 (16)0.0489 (14)0.0276 (14)0.0033 (13)0.0027 (11)
N60.0783 (19)0.0635 (16)0.0476 (14)0.0434 (15)0.0100 (13)0.0122 (12)
N70.0636 (17)0.0585 (15)0.0433 (13)0.0381 (14)0.0109 (12)0.0121 (11)
N80.0637 (17)0.0608 (15)0.0520 (14)0.0397 (14)0.0067 (13)0.0029 (12)
N90.0709 (18)0.0597 (16)0.0541 (14)0.0434 (15)0.0030 (13)0.0027 (12)
N100.0669 (18)0.0655 (16)0.0507 (14)0.0405 (15)0.0042 (13)0.0044 (12)
C10.0474 (18)0.0410 (17)0.0583 (18)0.0174 (15)0.0007 (15)0.0030 (13)
C20.056 (2)0.064 (2)0.0404 (15)0.0223 (17)0.0039 (14)0.0088 (15)
C30.0569 (19)0.0524 (18)0.0384 (15)0.0235 (16)0.0071 (14)0.0025 (13)
C40.0432 (17)0.0391 (15)0.0452 (15)0.0171 (14)0.0063 (13)0.0007 (12)
C50.0462 (18)0.0462 (17)0.0489 (16)0.0175 (15)0.0052 (14)0.0045 (13)
C60.0421 (17)0.0388 (15)0.0440 (15)0.0146 (14)0.0080 (13)0.0034 (12)
C70.0469 (18)0.0504 (18)0.0423 (15)0.0213 (15)0.0015 (13)0.0022 (13)
C80.071 (2)0.070 (2)0.0595 (19)0.0301 (19)0.0120 (17)0.0123 (16)
C90.084 (3)0.0417 (18)0.084 (2)0.0206 (18)0.002 (2)0.0019 (16)
C100.0402 (16)0.0420 (15)0.0409 (15)0.0165 (14)0.0063 (13)0.0018 (12)
C110.0389 (16)0.0330 (14)0.0412 (15)0.0109 (13)0.0074 (13)0.0010 (11)
C120.0391 (16)0.0437 (16)0.0516 (17)0.0205 (14)0.0081 (14)0.0044 (12)
C130.0486 (18)0.0465 (16)0.0481 (16)0.0239 (14)0.0071 (14)0.0075 (13)
C140.069 (2)0.086 (2)0.0565 (18)0.044 (2)0.0072 (17)0.0189 (17)
C150.055 (2)0.0575 (18)0.0426 (15)0.0253 (16)0.0092 (15)0.0066 (13)
C160.0399 (17)0.0429 (16)0.0582 (18)0.0147 (14)0.0099 (14)0.0011 (13)
C170.049 (2)0.088 (2)0.072 (2)0.0328 (19)0.0114 (17)0.0043 (18)
C180.0389 (16)0.0439 (16)0.0450 (15)0.0150 (13)0.0010 (13)0.0008 (12)
C190.058 (2)0.0592 (18)0.0425 (15)0.0340 (17)0.0058 (14)0.0055 (14)
C200.084 (2)0.069 (2)0.0481 (17)0.046 (2)0.0195 (17)0.0214 (15)
C210.070 (2)0.0554 (18)0.0427 (16)0.0352 (17)0.0133 (15)0.0057 (13)
C220.0549 (18)0.0438 (15)0.0399 (15)0.0264 (15)0.0013 (14)0.0014 (12)
C230.063 (2)0.0488 (17)0.0440 (15)0.0292 (16)0.0026 (14)0.0038 (13)
C240.0555 (18)0.0462 (16)0.0368 (14)0.0295 (15)0.0037 (13)0.0029 (12)
C250.0551 (18)0.0470 (16)0.0398 (15)0.0266 (15)0.0082 (14)0.0060 (12)
C260.073 (2)0.064 (2)0.0519 (17)0.0333 (19)0.0017 (16)0.0119 (15)
C270.102 (3)0.087 (3)0.113 (3)0.073 (3)0.002 (2)0.014 (2)
C280.061 (2)0.0404 (16)0.0392 (15)0.0230 (15)0.0069 (14)0.0026 (12)
C290.0583 (19)0.0400 (15)0.0400 (14)0.0288 (15)0.0057 (14)0.0016 (12)
C300.0452 (17)0.0401 (15)0.0575 (18)0.0195 (14)0.0038 (14)0.0038 (13)
C310.0498 (18)0.0490 (17)0.0510 (17)0.0280 (15)0.0052 (14)0.0072 (13)
C320.069 (2)0.073 (2)0.063 (2)0.0299 (19)0.0113 (18)0.0082 (17)
C330.060 (2)0.0532 (17)0.0440 (15)0.0327 (17)0.0019 (15)0.0022 (13)
C340.0553 (18)0.0391 (15)0.0483 (16)0.0266 (14)0.0060 (14)0.0003 (13)
C350.068 (2)0.0476 (18)0.0647 (19)0.0211 (17)0.0113 (17)0.0018 (15)
C360.0555 (19)0.0369 (15)0.0482 (16)0.0221 (15)0.0002 (14)0.0066 (12)
Geometric parameters (Å, º) top
Cl1—C11.735 (3)C12—H120.9300
Cl2—C191.731 (3)C13—C151.386 (4)
O1—C41.358 (3)C13—C141.511 (4)
O1—N31.450 (3)C14—H14A0.9600
O2—C101.352 (3)C14—H14B0.9600
O2—C111.406 (3)C14—H14C0.9600
O3—C221.352 (3)C15—C161.383 (4)
O3—N81.441 (3)C15—H150.9300
O4—C281.359 (3)C16—C181.393 (4)
O4—C291.410 (3)C16—C171.510 (4)
N1—C11.306 (4)C17—H17A0.9600
N1—C21.347 (4)C17—H17B0.9600
N2—C11.323 (3)C17—H17C0.9600
N2—C41.325 (3)C18—H180.9300
N3—C51.272 (3)C20—C211.364 (4)
N4—C101.332 (3)C20—H200.9300
N4—N51.371 (3)C21—C221.380 (4)
N4—C91.459 (4)C21—H210.9300
N5—C71.331 (3)C23—C241.435 (4)
N6—C191.314 (3)C23—H230.9300
N6—C201.351 (4)C24—C281.381 (4)
N7—C191.317 (3)C24—C251.410 (4)
N7—C221.325 (3)C25—C261.494 (4)
N8—C231.278 (3)C26—H26A0.9600
N9—C281.332 (4)C26—H26B0.9600
N9—N101.374 (3)C26—H26C0.9600
N9—C271.456 (4)C27—H27A0.9600
N10—C251.321 (3)C27—H27B0.9600
C2—C31.368 (4)C27—H27C0.9600
C2—H20.9300C29—C301.372 (4)
C3—C41.382 (4)C29—C361.373 (4)
C3—H30.9300C30—C311.384 (4)
C5—C61.437 (4)C30—H300.9300
C5—H50.9300C31—C331.391 (4)
C6—C101.382 (4)C31—C321.509 (4)
C6—C71.411 (4)C32—H32A0.9600
C7—C81.488 (4)C32—H32B0.9600
C8—H8A0.9600C32—H32C0.9600
C8—H8B0.9600C33—C341.385 (4)
C8—H8C0.9600C33—H330.9300
C9—H9A0.9600C34—C361.394 (4)
C9—H9B0.9600C34—C351.498 (4)
C9—H9C0.9600C35—H35A0.9600
C11—C121.376 (4)C35—H35B0.9600
C11—C181.377 (4)C35—H35C0.9600
C12—C131.385 (4)C36—H360.9300
C4—O1—N3112.4 (2)C16—C17—H17A109.5
C10—O2—C11118.1 (2)C16—C17—H17B109.5
C22—O3—N8112.9 (2)H17A—C17—H17B109.5
C28—O4—C29118.1 (2)C16—C17—H17C109.5
C1—N1—C2113.1 (2)H17A—C17—H17C109.5
C1—N2—C4113.8 (2)H17B—C17—H17C109.5
C5—N3—O1107.2 (2)C11—C18—C16118.9 (3)
C10—N4—N5111.8 (2)C11—C18—H18120.5
C10—N4—C9127.0 (3)C16—C18—H18120.5
N5—N4—C9121.2 (2)N6—C19—N7130.3 (3)
C7—N5—N4104.8 (2)N6—C19—Cl2115.1 (2)
C19—N6—C20112.4 (2)N7—C19—Cl2114.6 (2)
C19—N7—C22114.4 (2)N6—C20—C21124.4 (3)
C23—N8—O3107.8 (2)N6—C20—H20117.8
C28—N9—N10111.1 (2)C21—C20—H20117.8
C28—N9—C27128.7 (3)C20—C21—C22115.4 (3)
N10—N9—C27120.3 (3)C20—C21—H21122.3
C25—N10—N9105.1 (2)C22—C21—H21122.3
N1—C1—N2130.4 (3)N7—C22—O3111.5 (2)
N1—C1—Cl1115.3 (2)N7—C22—C21123.1 (3)
N2—C1—Cl1114.3 (2)O3—C22—C21125.4 (3)
N1—C2—C3123.7 (3)N8—C23—C24122.5 (3)
N1—C2—H2118.1N8—C23—H23118.7
C3—C2—H2118.1C24—C23—H23118.7
C2—C3—C4115.5 (3)C28—C24—C25103.9 (2)
C2—C3—H3122.3C28—C24—C23123.7 (3)
C4—C3—H3122.3C25—C24—C23132.4 (2)
N2—C4—O1111.5 (2)N10—C25—C24111.6 (2)
N2—C4—C3123.4 (3)N10—C25—C26119.6 (3)
O1—C4—C3125.2 (3)C24—C25—C26128.8 (3)
N3—C5—C6122.9 (3)C25—C26—H26A109.5
N3—C5—H5118.6C25—C26—H26B109.5
C6—C5—H5118.6H26A—C26—H26B109.5
C10—C6—C7104.3 (2)C25—C26—H26C109.5
C10—C6—C5123.6 (3)H26A—C26—H26C109.5
C7—C6—C5132.1 (3)H26B—C26—H26C109.5
N5—C7—C6111.3 (2)N9—C27—H27A109.5
N5—C7—C8120.0 (3)N9—C27—H27B109.5
C6—C7—C8128.6 (3)H27A—C27—H27B109.5
C7—C8—H8A109.5N9—C27—H27C109.5
C7—C8—H8B109.5H27A—C27—H27C109.5
H8A—C8—H8B109.5H27B—C27—H27C109.5
C7—C8—H8C109.5N9—C28—O4120.7 (2)
H8A—C8—H8C109.5N9—C28—C24108.3 (3)
H8B—C8—H8C109.5O4—C28—C24130.9 (3)
N4—C9—H9A109.5C30—C29—C36122.3 (2)
N4—C9—H9B109.5C30—C29—O4115.0 (2)
H9A—C9—H9B109.5C36—C29—O4122.6 (2)
N4—C9—H9C109.5C29—C30—C31119.6 (3)
H9A—C9—H9C109.5C29—C30—H30120.2
H9B—C9—H9C109.5C31—C30—H30120.2
N4—C10—O2121.2 (2)C30—C31—C33118.2 (3)
N4—C10—C6107.9 (2)C30—C31—C32121.0 (3)
O2—C10—C6130.7 (2)C33—C31—C32120.8 (3)
C12—C11—C18122.3 (2)C31—C32—H32A109.5
C12—C11—O2115.3 (2)C31—C32—H32B109.5
C18—C11—O2122.4 (2)H32A—C32—H32B109.5
C11—C12—C13119.4 (3)C31—C32—H32C109.5
C11—C12—H12120.3H32A—C32—H32C109.5
C13—C12—H12120.3H32B—C32—H32C109.5
C12—C13—C15118.5 (3)C34—C33—C31122.5 (3)
C12—C13—C14120.8 (3)C34—C33—H33118.8
C15—C13—C14120.8 (3)C31—C33—H33118.8
C13—C14—H14A109.5C33—C34—C36118.2 (3)
C13—C14—H14B109.5C33—C34—C35121.1 (2)
H14A—C14—H14B109.5C36—C34—C35120.7 (3)
C13—C14—H14C109.5C34—C35—H35A109.5
H14A—C14—H14C109.5C34—C35—H35B109.5
H14B—C14—H14C109.5H35A—C35—H35B109.5
C16—C15—C13122.3 (3)C34—C35—H35C109.5
C16—C15—H15118.9H35A—C35—H35C109.5
C13—C15—H15118.9H35B—C35—H35C109.5
C15—C16—C18118.7 (3)C29—C36—C34119.3 (3)
C15—C16—C17121.0 (3)C29—C36—H36120.4
C18—C16—C17120.3 (3)C34—C36—H36120.4
C4—O1—N3—C5175.6 (2)O2—C11—C18—C16178.6 (2)
C10—N4—N5—C70.0 (3)C15—C16—C18—C110.5 (4)
C9—N4—N5—C7179.0 (3)C17—C16—C18—C11179.6 (3)
C22—O3—N8—C23179.5 (2)C20—N6—C19—N71.4 (5)
C28—N9—N10—C250.4 (3)C20—N6—C19—Cl2179.2 (2)
C27—N9—N10—C25179.5 (3)C22—N7—C19—N60.4 (5)
C2—N1—C1—N21.0 (4)C22—N7—C19—Cl2179.9 (2)
C2—N1—C1—Cl1178.1 (2)C19—N6—C20—C211.7 (5)
C4—N2—C1—N10.3 (4)N6—C20—C21—C221.2 (5)
C4—N2—C1—Cl1178.8 (2)C19—N7—C22—O3179.8 (2)
C1—N1—C2—C30.2 (4)C19—N7—C22—C210.3 (4)
N1—C2—C3—C41.0 (4)N8—O3—C22—N7171.9 (2)
C1—N2—C4—O1178.9 (2)N8—O3—C22—C218.6 (4)
C1—N2—C4—C31.3 (4)C20—C21—C22—N70.1 (4)
N3—O1—C4—N2173.0 (2)C20—C21—C22—O3179.3 (3)
N3—O1—C4—C36.9 (4)O3—N8—C23—C24178.3 (2)
C2—C3—C4—N21.9 (4)N8—C23—C24—C28178.0 (3)
C2—C3—C4—O1178.3 (2)N8—C23—C24—C252.7 (5)
O1—N3—C5—C6178.2 (2)N9—N10—C25—C240.6 (3)
N3—C5—C6—C10173.8 (3)N9—N10—C25—C26179.1 (2)
N3—C5—C6—C76.7 (5)C28—C24—C25—N100.6 (3)
N4—N5—C7—C60.1 (3)C23—C24—C25—N10178.8 (3)
N4—N5—C7—C8179.6 (3)C28—C24—C25—C26178.9 (3)
C10—C6—C7—N50.1 (3)C23—C24—C25—C260.5 (5)
C5—C6—C7—N5179.5 (3)N10—N9—C28—O4176.1 (2)
C10—C6—C7—C8179.6 (3)C27—N9—C28—O44.0 (5)
C5—C6—C7—C80.0 (5)N10—N9—C28—C240.0 (3)
N5—N4—C10—O2174.5 (2)C27—N9—C28—C24179.8 (3)
C9—N4—C10—O26.5 (4)C29—O4—C28—N9106.4 (3)
N5—N4—C10—C60.1 (3)C29—O4—C28—C2478.4 (4)
C9—N4—C10—C6179.1 (3)C25—C24—C28—N90.3 (3)
C11—O2—C10—N4105.7 (3)C23—C24—C28—N9179.1 (2)
C11—O2—C10—C681.3 (3)C25—C24—C28—O4175.9 (3)
C7—C6—C10—N40.1 (3)C23—C24—C28—O43.5 (4)
C5—C6—C10—N4179.5 (2)C28—O4—C29—C30163.3 (2)
C7—C6—C10—O2173.8 (3)C28—O4—C29—C3618.6 (4)
C5—C6—C10—O25.8 (4)C36—C29—C30—C310.8 (4)
C10—O2—C11—C12163.6 (2)O4—C29—C30—C31178.9 (2)
C10—O2—C11—C1818.2 (3)C29—C30—C31—C330.3 (4)
C18—C11—C12—C130.2 (4)C29—C30—C31—C32179.0 (3)
O2—C11—C12—C13178.0 (2)C30—C31—C33—C340.7 (4)
C11—C12—C13—C150.9 (4)C32—C31—C33—C34178.7 (3)
C11—C12—C13—C14179.7 (3)C31—C33—C34—C360.1 (4)
C12—C13—C15—C160.9 (4)C31—C33—C34—C35179.9 (3)
C14—C13—C15—C16179.7 (3)C30—C29—C36—C341.5 (4)
C13—C15—C16—C180.2 (4)O4—C29—C36—C34179.5 (2)
C13—C15—C16—C17179.7 (3)C33—C34—C36—C291.1 (4)
C12—C11—C18—C160.5 (4)C35—C34—C36—C29179.0 (3)
 

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