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The asymmetric unit contains two independent mol­ecules of the title compound, C23H20ClNO2, with the same absolute configuration. Intra­molecular O—H...N hydrogen bonding is observed in both independent mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033125/xu2071sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033125/xu2071IIsup2.hkl
Contains datablock II

CCDC reference: 621540

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.077
  • wR factor = 0.241
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C10 .. 9.59 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C6 - C7 .. 7.62 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - C29 .. 13.81 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C25 - C26 .. 9.66 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.44 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 6.15 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C23 .. 5.59 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C40 - C41 .. 6.62 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C44 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.50 From the CIF: _reflns_number_total 7508 Count of symmetry unique reflns 4218 Completeness (_total/calc) 178.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3290 Fraction of Friedel pairs measured 0.780 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C37 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C45 = . R
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 17 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

4-Chloro-2-{[(R)-(3'S,8'R)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol- 3-yl](phenyl)methyl}phenol top
Crystal data top
C23H20ClNO2Dx = 1.245 Mg m3
Mr = 377.85Melting point = 531–532 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3355 reflections
a = 9.5270 (12) Åθ = 2.3–18.6°
b = 18.657 (2) ŵ = 0.21 mm1
c = 22.679 (3) ÅT = 298 K
V = 4031.2 (9) Å3Block, colourless
Z = 80.60 × 0.54 × 0.45 mm
F(000) = 1584
Data collection top
Bruker SMART CCD area-detector
diffractometer
4295 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.5°, θmin = 1.8°
φ and ω scansh = 1111
21356 measured reflectionsk = 1622
7508 independent reflectionsl = 2724
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)] = 0.077H-atom parameters constrained
wR(F2) = 0.241 w = 1/[σ2(Fo2) + (0.1469P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
7508 reflectionsΔρmax = 0.57 e Å3
487 parametersΔρmin = 0.42 e Å3
0 restraintsAbsolute structure: Flack (1983), 3287 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (13)
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
C10.2878 (5)0.5496 (4)0.5468 (2)0.0826 (16)
C20.2830 (6)0.6173 (4)0.5718 (3)0.0922 (17)
H2A0.34390.65300.55900.111*
C30.1871 (8)0.6313 (5)0.6159 (3)0.111 (2)
H30.18340.67690.63250.134*
C40.1004 (9)0.5813 (7)0.6350 (3)0.126 (3)
H4A0.03790.59170.66530.151*
C50.1017 (8)0.5104 (6)0.6091 (4)0.133 (3)
H50.03960.47520.62190.159*
C60.1985 (6)0.4959 (4)0.5644 (3)0.0925 (17)
C70.2205 (8)0.4307 (4)0.5327 (4)0.121 (3)
H7A0.13290.41350.51610.145*
H7B0.25840.39410.55850.145*
C80.3263 (7)0.4488 (3)0.4831 (3)0.0973 (18)
H80.40200.41340.48130.117*
C90.3823 (5)0.5222 (3)0.4984 (2)0.0738 (13)
H90.47950.51890.51230.089*
C100.2494 (5)0.5325 (5)0.4167 (2)0.101 (2)
H10A0.16390.55080.43440.122*
H10B0.24740.54260.37480.122*
C110.4993 (4)0.5640 (2)0.40472 (19)0.0605 (11)
H110.50540.51580.38780.073*
C120.4789 (4)0.6162 (3)0.35453 (19)0.0595 (11)
C130.4171 (5)0.6828 (3)0.3632 (2)0.0728 (14)
C140.4132 (7)0.7316 (4)0.3177 (3)0.1002 (19)
H140.37200.77620.32360.120*
C150.4697 (7)0.7149 (5)0.2636 (3)0.100 (2)
H150.46730.74790.23300.120*
C160.5297 (6)0.6487 (4)0.2555 (2)0.0893 (17)
C170.5334 (5)0.6017 (3)0.2998 (2)0.0716 (14)
H170.57470.55720.29330.086*
C180.6323 (5)0.5779 (2)0.43781 (18)0.0591 (11)
C190.7367 (5)0.5253 (3)0.4389 (2)0.0698 (13)
H190.72230.48160.42020.084*
C200.8630 (6)0.5388 (4)0.4682 (3)0.0948 (18)
H200.93160.50330.46840.114*
C210.8889 (6)0.5997 (4)0.4955 (3)0.0879 (16)
H210.97420.60730.51440.105*
C220.7871 (7)0.6513 (4)0.4953 (3)0.104 (2)
H220.80290.69410.51520.124*
C230.6590 (6)0.6411 (3)0.4657 (3)0.0896 (17)
H230.59250.67760.46500.108*
C240.6366 (9)0.3530 (4)0.3572 (4)0.120 (3)
H240.54060.35450.35000.144*
C250.6923 (11)0.3259 (3)0.4091 (4)0.120 (3)
H250.63170.30510.43630.144*
C260.8314 (8)0.3282 (3)0.4219 (3)0.101 (2)
C270.9207 (7)0.3509 (3)0.3795 (3)0.0921 (18)
H271.01640.34870.38740.111*
C280.8796 (7)0.3768 (3)0.3257 (3)0.0847 (15)
C290.7416 (7)0.3796 (3)0.3142 (3)0.0907 (17)
C300.9844 (6)0.3962 (3)0.2789 (2)0.0732 (13)
H301.07390.40580.29870.088*
C311.0082 (5)0.3357 (2)0.2361 (2)0.0671 (12)
C321.1106 (7)0.2869 (3)0.2476 (3)0.0940 (17)
H321.16510.29230.28130.113*
C331.1359 (8)0.2296 (3)0.2106 (4)0.110 (2)
H331.20890.19800.21870.132*
C341.0533 (8)0.2194 (3)0.1618 (3)0.101 (2)
H341.06890.18020.13730.121*
C350.9479 (7)0.2667 (3)0.1491 (3)0.0962 (18)
H350.89090.26000.11630.115*
C360.9278 (6)0.3243 (3)0.1858 (3)0.0883 (17)
H360.85750.35700.17670.106*
C371.0481 (5)0.4883 (2)0.20437 (19)0.0591 (11)
H371.09720.44770.18620.071*
C380.9863 (5)0.5378 (3)0.15889 (18)0.0618 (11)
C390.8808 (6)0.5247 (3)0.11902 (19)0.0770 (14)
H390.83970.47950.11640.092*
C400.8365 (7)0.5807 (5)0.0825 (2)0.106 (2)
H400.76580.57230.05510.127*
C410.8951 (11)0.6477 (5)0.0863 (3)0.122 (3)
H410.86140.68500.06310.147*
C421.0058 (9)0.6589 (4)0.1253 (3)0.108 (2)
H421.05090.70300.12640.130*
C431.0477 (6)0.6051 (3)0.1617 (2)0.0752 (14)
C441.1609 (7)0.6066 (4)0.2063 (3)0.0996 (19)
H44A1.14890.64690.23280.119*
H44B1.25200.61040.18740.119*
C451.1480 (5)0.5362 (3)0.2394 (2)0.0775 (14)
H451.24000.51340.24410.093*
C460.9387 (6)0.5240 (3)0.2877 (2)0.0717 (13)
H46A0.88290.56290.27170.086*
H46B0.89830.50960.32520.086*
N10.3745 (4)0.5660 (2)0.44453 (15)0.0666 (10)
N20.9409 (4)0.46430 (18)0.24736 (15)0.0602 (9)
O10.2617 (6)0.4581 (3)0.4267 (2)0.1235 (17)
O20.3587 (5)0.7026 (2)0.41557 (16)0.0988 (12)
H20.36660.66970.43930.148*
O31.0811 (4)0.5465 (2)0.29564 (14)0.0880 (11)
O40.6813 (4)0.4089 (3)0.2647 (2)0.1075 (14)
H40.74300.42450.24290.161*
Cl10.6075 (2)0.62902 (16)0.18796 (7)0.1484 (10)
Cl20.8897 (3)0.29449 (13)0.48823 (9)0.1505 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.052 (3)0.127 (5)0.068 (3)0.008 (3)0.015 (2)0.020 (4)
C20.082 (4)0.123 (5)0.071 (3)0.015 (4)0.010 (3)0.002 (4)
C30.097 (5)0.166 (7)0.071 (4)0.017 (5)0.006 (4)0.003 (4)
C40.096 (5)0.195 (10)0.086 (5)0.005 (6)0.001 (4)0.025 (6)
C50.082 (5)0.201 (9)0.115 (6)0.032 (6)0.021 (5)0.080 (6)
C60.072 (4)0.115 (5)0.090 (4)0.013 (4)0.014 (3)0.020 (4)
C70.111 (5)0.119 (6)0.134 (6)0.044 (5)0.047 (5)0.051 (5)
C80.089 (4)0.096 (4)0.107 (4)0.008 (3)0.035 (4)0.005 (4)
C90.054 (3)0.094 (4)0.074 (3)0.000 (3)0.017 (2)0.006 (3)
C100.051 (3)0.185 (8)0.068 (3)0.014 (4)0.021 (2)0.004 (4)
C110.049 (2)0.062 (3)0.070 (3)0.007 (2)0.017 (2)0.020 (2)
C120.043 (2)0.074 (3)0.061 (2)0.005 (2)0.007 (2)0.015 (2)
C130.060 (3)0.093 (4)0.065 (3)0.021 (3)0.008 (2)0.005 (3)
C140.084 (4)0.109 (5)0.107 (5)0.020 (4)0.009 (4)0.010 (4)
C150.083 (4)0.138 (6)0.080 (4)0.012 (4)0.012 (3)0.029 (4)
C160.078 (4)0.131 (5)0.059 (3)0.020 (4)0.001 (3)0.012 (4)
C170.054 (3)0.096 (4)0.064 (3)0.005 (2)0.006 (2)0.025 (3)
C180.050 (2)0.072 (3)0.056 (2)0.005 (2)0.007 (2)0.010 (2)
C190.045 (2)0.079 (3)0.085 (3)0.003 (2)0.008 (2)0.001 (3)
C200.063 (3)0.099 (4)0.122 (5)0.017 (3)0.024 (3)0.009 (4)
C210.057 (3)0.117 (5)0.090 (4)0.003 (3)0.024 (3)0.003 (4)
C220.103 (5)0.094 (4)0.113 (5)0.021 (4)0.020 (4)0.021 (4)
C230.065 (3)0.089 (4)0.115 (4)0.007 (3)0.031 (3)0.038 (4)
C240.121 (5)0.120 (5)0.119 (6)0.020 (5)0.050 (5)0.051 (5)
C250.170 (9)0.073 (4)0.116 (6)0.029 (4)0.061 (6)0.018 (4)
C260.100 (5)0.089 (4)0.112 (5)0.005 (4)0.033 (4)0.003 (4)
C270.110 (5)0.070 (3)0.096 (4)0.014 (3)0.026 (4)0.016 (3)
C280.093 (4)0.066 (3)0.095 (4)0.006 (3)0.010 (3)0.007 (3)
C290.092 (4)0.091 (4)0.089 (4)0.016 (3)0.016 (4)0.011 (3)
C300.075 (3)0.067 (3)0.077 (3)0.009 (3)0.012 (3)0.009 (3)
C310.065 (3)0.058 (3)0.079 (3)0.010 (2)0.015 (3)0.010 (2)
C320.106 (4)0.088 (4)0.088 (4)0.021 (4)0.011 (4)0.006 (3)
C330.101 (5)0.078 (4)0.152 (6)0.041 (4)0.016 (5)0.006 (4)
C340.113 (5)0.069 (4)0.120 (5)0.005 (4)0.036 (4)0.007 (4)
C350.085 (4)0.084 (4)0.120 (5)0.004 (3)0.014 (3)0.028 (4)
C360.064 (3)0.077 (4)0.124 (5)0.015 (3)0.009 (3)0.015 (3)
C370.054 (2)0.062 (3)0.061 (3)0.003 (2)0.006 (2)0.004 (2)
C380.068 (3)0.072 (3)0.046 (2)0.001 (3)0.008 (2)0.004 (2)
C390.086 (3)0.095 (4)0.050 (2)0.011 (3)0.001 (3)0.010 (3)
C400.096 (4)0.177 (7)0.044 (3)0.058 (5)0.007 (3)0.006 (4)
C410.180 (8)0.109 (6)0.078 (4)0.042 (6)0.026 (5)0.014 (4)
C420.147 (7)0.090 (4)0.088 (4)0.001 (5)0.039 (5)0.017 (4)
C430.091 (4)0.077 (3)0.058 (3)0.007 (3)0.010 (3)0.008 (3)
C440.094 (4)0.108 (4)0.097 (4)0.037 (4)0.011 (3)0.013 (4)
C450.061 (3)0.093 (4)0.079 (3)0.006 (3)0.014 (3)0.001 (3)
C460.091 (4)0.069 (3)0.055 (2)0.000 (3)0.005 (2)0.006 (2)
N10.0445 (19)0.098 (3)0.057 (2)0.001 (2)0.0093 (17)0.002 (2)
N20.066 (2)0.0515 (19)0.063 (2)0.0046 (17)0.0071 (18)0.0015 (18)
O10.140 (4)0.123 (4)0.108 (3)0.058 (3)0.047 (3)0.011 (3)
O20.109 (3)0.105 (3)0.082 (2)0.049 (2)0.010 (2)0.014 (2)
O30.103 (3)0.105 (3)0.0558 (18)0.015 (2)0.0176 (18)0.0075 (18)
O40.058 (2)0.131 (3)0.133 (4)0.004 (2)0.017 (2)0.043 (3)
Cl10.1316 (16)0.244 (3)0.0694 (9)0.0521 (17)0.0276 (10)0.0383 (12)
Cl20.205 (2)0.1392 (16)0.1069 (12)0.0437 (16)0.0530 (15)0.0297 (12)
Geometric parameters (Å, º) top
C1—C61.374 (8)C24—C291.482 (9)
C1—C21.386 (9)C24—H240.9300
C1—C91.509 (8)C25—C261.357 (11)
C2—C31.380 (9)C25—H250.9300
C2—H2A0.9300C26—C271.351 (9)
C3—C41.319 (11)C26—Cl21.722 (8)
C3—H30.9300C27—C281.371 (8)
C4—C51.448 (12)C27—H270.9300
C4—H4A0.9300C28—C291.342 (9)
C5—C61.397 (11)C28—C301.500 (8)
C5—H50.9300C29—O41.375 (7)
C6—C71.428 (10)C30—C311.507 (7)
C7—C81.547 (10)C30—N21.515 (6)
C7—H7A0.9700C30—H300.9800
C7—H7B0.9700C31—C321.360 (8)
C8—O11.431 (7)C31—C361.390 (8)
C8—C91.510 (8)C32—C331.380 (9)
C8—H80.9800C32—H320.9300
C9—N11.471 (6)C33—C341.371 (10)
C9—H90.9800C33—H330.9300
C10—O11.411 (9)C34—C351.368 (9)
C10—N11.486 (6)C34—H340.9300
C10—H10A0.9700C35—C361.372 (8)
C10—H10B0.9700C35—H350.9300
C11—N11.494 (6)C36—H360.9300
C11—C181.495 (6)C37—N21.481 (6)
C11—C121.510 (6)C37—C381.505 (6)
C11—H110.9800C37—C451.529 (6)
C12—C171.373 (6)C37—H370.9800
C12—C131.389 (7)C38—C391.375 (7)
C13—O21.363 (6)C38—C431.387 (7)
C13—C141.376 (8)C39—C401.398 (9)
C14—C151.375 (9)C39—H390.9300
C14—H140.9300C40—C411.372 (11)
C15—C161.373 (10)C40—H400.9300
C15—H150.9300C41—C421.392 (11)
C16—C171.333 (8)C41—H410.9300
C16—Cl11.742 (6)C42—C431.359 (8)
C17—H170.9300C42—H420.9300
C18—C231.362 (6)C43—C441.478 (8)
C18—C191.397 (6)C44—C451.518 (9)
C19—C201.397 (7)C44—H44A0.9700
C19—H190.9300C44—H44B0.9700
C20—C211.318 (8)C45—O31.439 (6)
C20—H200.9300C45—H450.9800
C21—C221.367 (9)C46—O31.432 (6)
C21—H210.9300C46—N21.442 (6)
C22—C231.407 (8)C46—H46A0.9700
C22—H220.9300C46—H46B0.9700
C23—H230.9300O2—H20.8200
C24—C251.386 (11)O4—H40.8200
C6—C1—C2121.8 (6)C24—C25—H25118.5
C6—C1—C9109.5 (6)C27—C26—C25118.2 (7)
C2—C1—C9128.7 (5)C27—C26—Cl2122.2 (6)
C3—C2—C1119.4 (7)C25—C26—Cl2119.4 (6)
C3—C2—H2A120.3C26—C27—C28124.4 (7)
C1—C2—H2A120.3C26—C27—H27117.8
C4—C3—C2121.3 (8)C28—C27—H27117.8
C4—C3—H3119.4C29—C28—C27117.8 (6)
C2—C3—H3119.4C29—C28—C30120.4 (6)
C3—C4—C5120.5 (8)C27—C28—C30121.6 (6)
C3—C4—H4A119.7C28—C29—O4125.7 (6)
C5—C4—H4A119.7C28—C29—C24121.3 (7)
C6—C5—C4118.5 (7)O4—C29—C24112.9 (6)
C6—C5—H5120.8C28—C30—C31112.0 (4)
C4—C5—H5120.8C28—C30—N2110.8 (4)
C1—C6—C5118.6 (8)C31—C30—N2111.4 (4)
C1—C6—C7112.6 (6)C28—C30—H30107.5
C5—C6—C7128.9 (8)C31—C30—H30107.5
C6—C7—C8106.0 (5)N2—C30—H30107.5
C6—C7—H7A110.5C32—C31—C36116.7 (5)
C8—C7—H7A110.5C32—C31—C30119.1 (5)
C6—C7—H7B110.5C36—C31—C30124.1 (4)
C8—C7—H7B110.5C31—C32—C33121.8 (6)
H7A—C7—H7B108.7C31—C32—H32119.1
O1—C8—C9104.3 (5)C33—C32—H32119.1
O1—C8—C7113.3 (5)C34—C33—C32119.9 (6)
C9—C8—C7105.2 (6)C34—C33—H33120.1
O1—C8—H8111.2C32—C33—H33120.1
C9—C8—H8111.2C35—C34—C33120.1 (6)
C7—C8—H8111.2C35—C34—H34120.0
N1—C9—C1112.8 (4)C33—C34—H34120.0
N1—C9—C8107.2 (4)C34—C35—C36118.7 (7)
C1—C9—C8105.2 (5)C34—C35—H35120.7
N1—C9—H9110.5C36—C35—H35120.7
C1—C9—H9110.5C35—C36—C31122.8 (6)
C8—C9—H9110.5C35—C36—H36118.6
O1—C10—N1106.2 (5)C31—C36—H36118.6
O1—C10—H10A110.5N2—C37—C38111.6 (4)
N1—C10—H10A110.5N2—C37—C45105.3 (3)
O1—C10—H10B110.5C38—C37—C45103.9 (4)
N1—C10—H10B110.5N2—C37—H37111.9
H10A—C10—H10B108.7C38—C37—H37111.9
N1—C11—C18111.5 (3)C45—C37—H37111.9
N1—C11—C12109.7 (3)C39—C38—C43120.0 (5)
C18—C11—C12112.1 (4)C39—C38—C37128.8 (4)
N1—C11—H11107.8C43—C38—C37111.1 (4)
C18—C11—H11107.8C38—C39—C40118.4 (6)
C12—C11—H11107.8C38—C39—H39120.8
C17—C12—C13117.6 (5)C40—C39—H39120.8
C17—C12—C11120.4 (4)C41—C40—C39121.4 (6)
C13—C12—C11121.7 (4)C41—C40—H40119.3
O2—C13—C14117.5 (5)C39—C40—H40119.3
O2—C13—C12122.6 (4)C40—C41—C42119.0 (7)
C14—C13—C12119.9 (5)C40—C41—H41120.5
C15—C14—C13120.5 (6)C42—C41—H41120.5
C15—C14—H14119.8C43—C42—C41119.9 (7)
C13—C14—H14119.8C43—C42—H42120.1
C16—C15—C14119.1 (6)C41—C42—H42120.1
C16—C15—H15120.5C42—C43—C38121.1 (6)
C14—C15—H15120.5C42—C43—C44128.0 (6)
C17—C16—C15120.1 (5)C38—C43—C44110.8 (5)
C17—C16—Cl1120.8 (6)C43—C44—C45105.3 (4)
C15—C16—Cl1119.0 (6)C43—C44—H44A110.7
C16—C17—C12122.8 (5)C45—C44—H44A110.7
C16—C17—H17118.6C43—C44—H44B110.7
C12—C17—H17118.6C45—C44—H44B110.7
C23—C18—C19117.8 (4)H44A—C44—H44B108.8
C23—C18—C11122.7 (4)O3—C45—C44111.1 (5)
C19—C18—C11119.4 (4)O3—C45—C37105.2 (4)
C18—C19—C20119.8 (5)C44—C45—C37107.4 (4)
C18—C19—H19120.1O3—C45—H45111.0
C20—C19—H19120.1C44—C45—H45111.0
C21—C20—C19122.7 (5)C37—C45—H45111.0
C21—C20—H20118.7O3—C46—N2107.0 (4)
C19—C20—H20118.7O3—C46—H46A110.3
C20—C21—C22118.3 (5)N2—C46—H46A110.3
C20—C21—H21120.9O3—C46—H46B110.3
C22—C21—H21120.9N2—C46—H46B110.3
C21—C22—C23121.4 (6)H46A—C46—H46B108.6
C21—C22—H22119.3C9—N1—C1099.2 (4)
C23—C22—H22119.3C9—N1—C11116.6 (3)
C18—C23—C22120.1 (5)C10—N1—C11111.8 (3)
C18—C23—H23119.9C46—N2—C37101.2 (3)
C22—C23—H23120.0C46—N2—C30110.6 (3)
C25—C24—C29115.0 (7)C37—N2—C30112.1 (3)
C25—C24—H24122.5C10—O1—C8107.3 (4)
C29—C24—H24122.5C13—O2—H2109.5
C26—C25—C24123.0 (7)C46—O3—C45105.7 (3)
C26—C25—H25118.5C29—O4—H4109.5
C6—C1—C2—C30.6 (8)C29—C28—C30—C3180.1 (6)
C9—C1—C2—C3179.7 (5)C27—C28—C30—C3195.1 (6)
C1—C2—C3—C40.4 (9)C29—C28—C30—N244.9 (7)
C2—C3—C4—C51.3 (11)C27—C28—C30—N2139.9 (5)
C3—C4—C5—C61.2 (11)C28—C30—C31—C3289.9 (6)
C2—C1—C6—C50.7 (8)N2—C30—C31—C32145.5 (5)
C9—C1—C6—C5179.9 (5)C28—C30—C31—C3687.5 (6)
C2—C1—C6—C7179.5 (5)N2—C30—C31—C3637.2 (7)
C9—C1—C6—C70.3 (7)C36—C31—C32—C331.4 (9)
C4—C5—C6—C10.2 (9)C30—C31—C32—C33178.9 (5)
C4—C5—C6—C7179.6 (7)C31—C32—C33—C342.4 (10)
C1—C6—C7—C87.8 (7)C32—C33—C34—C351.4 (10)
C5—C6—C7—C8172.5 (6)C33—C34—C35—C360.4 (10)
C6—C7—C8—O1101.5 (6)C34—C35—C36—C311.4 (9)
C6—C7—C8—C911.9 (6)C32—C31—C36—C350.5 (8)
C6—C1—C9—N1123.9 (5)C30—C31—C36—C35176.8 (5)
C2—C1—C9—N155.3 (7)N2—C37—C38—C3960.6 (6)
C6—C1—C9—C87.5 (5)C45—C37—C38—C39173.6 (5)
C2—C1—C9—C8171.7 (5)N2—C37—C38—C43117.6 (4)
O1—C8—C9—N112.2 (6)C45—C37—C38—C434.6 (5)
C7—C8—C9—N1131.8 (5)C43—C38—C39—C400.9 (7)
O1—C8—C9—C1108.0 (5)C37—C38—C39—C40177.2 (4)
C7—C8—C9—C111.6 (5)C38—C39—C40—C410.6 (8)
N1—C11—C12—C17147.1 (4)C39—C40—C41—C423.3 (10)
C18—C11—C12—C1788.4 (5)C40—C41—C42—C434.4 (10)
N1—C11—C12—C1339.1 (5)C41—C42—C43—C383.0 (9)
C18—C11—C12—C1385.4 (5)C41—C42—C43—C44179.2 (6)
C17—C12—C13—O2179.5 (5)C39—C38—C43—C420.3 (7)
C11—C12—C13—O26.6 (7)C37—C38—C43—C42178.7 (5)
C17—C12—C13—C140.5 (7)C39—C38—C43—C44178.4 (5)
C11—C12—C13—C14173.4 (5)C37—C38—C43—C443.2 (6)
O2—C13—C14—C15179.7 (6)C42—C43—C44—C45172.3 (6)
C12—C13—C14—C150.2 (9)C38—C43—C44—C459.7 (6)
C13—C14—C15—C160.2 (10)C43—C44—C45—O3102.2 (5)
C14—C15—C16—C170.3 (9)C43—C44—C45—C3712.3 (6)
C14—C15—C16—Cl1177.4 (5)N2—C37—C45—O39.4 (5)
C15—C16—C17—C120.0 (8)C38—C37—C45—O3108.0 (4)
Cl1—C16—C17—C12177.1 (4)N2—C37—C45—C44127.8 (4)
C13—C12—C17—C160.4 (7)C38—C37—C45—C4410.4 (5)
C11—C12—C17—C16173.6 (4)C1—C9—N1—C1084.4 (5)
N1—C11—C18—C2363.3 (6)C8—C9—N1—C1030.9 (5)
C12—C11—C18—C2360.1 (6)C1—C9—N1—C11155.5 (4)
N1—C11—C18—C19119.1 (4)C8—C9—N1—C1189.2 (5)
C12—C11—C18—C19117.5 (5)O1—C10—N1—C939.9 (5)
C23—C18—C19—C200.3 (8)O1—C10—N1—C1183.7 (5)
C11—C18—C19—C20178.0 (5)C18—C11—N1—C950.5 (5)
C18—C19—C20—C210.2 (9)C12—C11—N1—C9175.4 (4)
C19—C20—C21—C220.5 (10)C18—C11—N1—C10163.7 (5)
C20—C21—C22—C231.6 (10)C12—C11—N1—C1071.5 (5)
C19—C18—C23—C221.4 (8)O3—C46—N2—C3740.2 (4)
C11—C18—C23—C22179.0 (5)O3—C46—N2—C3078.7 (5)
C21—C22—C23—C182.1 (10)C38—C37—N2—C4682.6 (4)
C29—C24—C25—C264.9 (10)C45—C37—N2—C4629.4 (4)
C24—C25—C26—C277.4 (10)C38—C37—N2—C30159.5 (4)
C24—C25—C26—Cl2178.7 (5)C45—C37—N2—C3088.4 (4)
C25—C26—C27—C285.0 (10)C28—C30—N2—C4663.1 (5)
Cl2—C26—C27—C28178.7 (5)C31—C30—N2—C46171.6 (4)
C26—C27—C28—C290.2 (9)C28—C30—N2—C37175.3 (4)
C26—C27—C28—C30175.6 (5)C31—C30—N2—C3759.4 (5)
C27—C28—C29—O4174.7 (5)N1—C10—O1—C834.3 (6)
C30—C28—C29—O49.8 (9)C9—C8—O1—C1013.4 (7)
C27—C28—C29—C242.3 (9)C7—C8—O1—C10100.5 (7)
C30—C28—C29—C24173.1 (5)N2—C46—O3—C4535.3 (5)
C25—C24—C29—C280.1 (9)C44—C45—O3—C46101.0 (5)
C25—C24—C29—O4177.3 (5)C37—C45—O3—C4614.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.942.636 (5)142
O4—H4···N20.822.032.709 (6)140
 

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