The asymmetric unit contains two independent molecules of the title compound, C
23H
20ClNO
2, with the same absolute configuration. Intramolecular O—H
N hydrogen bonding is observed in both independent molecules.
Supporting information
CCDC reference: 621540
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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-2
H-indeno[1,2-
d][1,3]oxazol- 3-yl](phenyl)methyl}phenol
top
Crystal data top
C23H20ClNO2 | Dx = 1.245 Mg m−3 |
Mr = 377.85 | Melting point = 531–532 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3355 reflections |
a = 9.5270 (12) Å | θ = 2.3–18.6° |
b = 18.657 (2) Å | µ = 0.21 mm−1 |
c = 22.679 (3) Å | T = 298 K |
V = 4031.2 (9) Å3 | Block, colourless |
Z = 8 | 0.60 × 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 tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.5°, θmin = 1.8° |
φ and ω scans | h = −11→11 |
21356 measured reflections | k = −16→22 |
7508 independent reflections | l = −27→24 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.077 | H-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 reflections | Δρmax = 0.57 e Å−3 |
487 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 3287 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2878 (5) | 0.5496 (4) | 0.5468 (2) | 0.0826 (16) | |
C2 | 0.2830 (6) | 0.6173 (4) | 0.5718 (3) | 0.0922 (17) | |
H2A | 0.3439 | 0.6530 | 0.5590 | 0.111* | |
C3 | 0.1871 (8) | 0.6313 (5) | 0.6159 (3) | 0.111 (2) | |
H3 | 0.1834 | 0.6769 | 0.6325 | 0.134* | |
C4 | 0.1004 (9) | 0.5813 (7) | 0.6350 (3) | 0.126 (3) | |
H4A | 0.0379 | 0.5917 | 0.6653 | 0.151* | |
C5 | 0.1017 (8) | 0.5104 (6) | 0.6091 (4) | 0.133 (3) | |
H5 | 0.0396 | 0.4752 | 0.6219 | 0.159* | |
C6 | 0.1985 (6) | 0.4959 (4) | 0.5644 (3) | 0.0925 (17) | |
C7 | 0.2205 (8) | 0.4307 (4) | 0.5327 (4) | 0.121 (3) | |
H7A | 0.1329 | 0.4135 | 0.5161 | 0.145* | |
H7B | 0.2584 | 0.3941 | 0.5585 | 0.145* | |
C8 | 0.3263 (7) | 0.4488 (3) | 0.4831 (3) | 0.0973 (18) | |
H8 | 0.4020 | 0.4134 | 0.4813 | 0.117* | |
C9 | 0.3823 (5) | 0.5222 (3) | 0.4984 (2) | 0.0738 (13) | |
H9 | 0.4795 | 0.5189 | 0.5123 | 0.089* | |
C10 | 0.2494 (5) | 0.5325 (5) | 0.4167 (2) | 0.101 (2) | |
H10A | 0.1639 | 0.5508 | 0.4344 | 0.122* | |
H10B | 0.2474 | 0.5426 | 0.3748 | 0.122* | |
C11 | 0.4993 (4) | 0.5640 (2) | 0.40472 (19) | 0.0605 (11) | |
H11 | 0.5054 | 0.5158 | 0.3878 | 0.073* | |
C12 | 0.4789 (4) | 0.6162 (3) | 0.35453 (19) | 0.0595 (11) | |
C13 | 0.4171 (5) | 0.6828 (3) | 0.3632 (2) | 0.0728 (14) | |
C14 | 0.4132 (7) | 0.7316 (4) | 0.3177 (3) | 0.1002 (19) | |
H14 | 0.3720 | 0.7762 | 0.3236 | 0.120* | |
C15 | 0.4697 (7) | 0.7149 (5) | 0.2636 (3) | 0.100 (2) | |
H15 | 0.4673 | 0.7479 | 0.2330 | 0.120* | |
C16 | 0.5297 (6) | 0.6487 (4) | 0.2555 (2) | 0.0893 (17) | |
C17 | 0.5334 (5) | 0.6017 (3) | 0.2998 (2) | 0.0716 (14) | |
H17 | 0.5747 | 0.5572 | 0.2933 | 0.086* | |
C18 | 0.6323 (5) | 0.5779 (2) | 0.43781 (18) | 0.0591 (11) | |
C19 | 0.7367 (5) | 0.5253 (3) | 0.4389 (2) | 0.0698 (13) | |
H19 | 0.7223 | 0.4816 | 0.4202 | 0.084* | |
C20 | 0.8630 (6) | 0.5388 (4) | 0.4682 (3) | 0.0948 (18) | |
H20 | 0.9316 | 0.5033 | 0.4684 | 0.114* | |
C21 | 0.8889 (6) | 0.5997 (4) | 0.4955 (3) | 0.0879 (16) | |
H21 | 0.9742 | 0.6073 | 0.5144 | 0.105* | |
C22 | 0.7871 (7) | 0.6513 (4) | 0.4953 (3) | 0.104 (2) | |
H22 | 0.8029 | 0.6941 | 0.5152 | 0.124* | |
C23 | 0.6590 (6) | 0.6411 (3) | 0.4657 (3) | 0.0896 (17) | |
H23 | 0.5925 | 0.6776 | 0.4650 | 0.108* | |
C24 | 0.6366 (9) | 0.3530 (4) | 0.3572 (4) | 0.120 (3) | |
H24 | 0.5406 | 0.3545 | 0.3500 | 0.144* | |
C25 | 0.6923 (11) | 0.3259 (3) | 0.4091 (4) | 0.120 (3) | |
H25 | 0.6317 | 0.3051 | 0.4363 | 0.144* | |
C26 | 0.8314 (8) | 0.3282 (3) | 0.4219 (3) | 0.101 (2) | |
C27 | 0.9207 (7) | 0.3509 (3) | 0.3795 (3) | 0.0921 (18) | |
H27 | 1.0164 | 0.3487 | 0.3874 | 0.111* | |
C28 | 0.8796 (7) | 0.3768 (3) | 0.3257 (3) | 0.0847 (15) | |
C29 | 0.7416 (7) | 0.3796 (3) | 0.3142 (3) | 0.0907 (17) | |
C30 | 0.9844 (6) | 0.3962 (3) | 0.2789 (2) | 0.0732 (13) | |
H30 | 1.0739 | 0.4058 | 0.2987 | 0.088* | |
C31 | 1.0082 (5) | 0.3357 (2) | 0.2361 (2) | 0.0671 (12) | |
C32 | 1.1106 (7) | 0.2869 (3) | 0.2476 (3) | 0.0940 (17) | |
H32 | 1.1651 | 0.2923 | 0.2813 | 0.113* | |
C33 | 1.1359 (8) | 0.2296 (3) | 0.2106 (4) | 0.110 (2) | |
H33 | 1.2089 | 0.1980 | 0.2187 | 0.132* | |
C34 | 1.0533 (8) | 0.2194 (3) | 0.1618 (3) | 0.101 (2) | |
H34 | 1.0689 | 0.1802 | 0.1373 | 0.121* | |
C35 | 0.9479 (7) | 0.2667 (3) | 0.1491 (3) | 0.0962 (18) | |
H35 | 0.8909 | 0.2600 | 0.1163 | 0.115* | |
C36 | 0.9278 (6) | 0.3243 (3) | 0.1858 (3) | 0.0883 (17) | |
H36 | 0.8575 | 0.3570 | 0.1767 | 0.106* | |
C37 | 1.0481 (5) | 0.4883 (2) | 0.20437 (19) | 0.0591 (11) | |
H37 | 1.0972 | 0.4477 | 0.1862 | 0.071* | |
C38 | 0.9863 (5) | 0.5378 (3) | 0.15889 (18) | 0.0618 (11) | |
C39 | 0.8808 (6) | 0.5247 (3) | 0.11902 (19) | 0.0770 (14) | |
H39 | 0.8397 | 0.4795 | 0.1164 | 0.092* | |
C40 | 0.8365 (7) | 0.5807 (5) | 0.0825 (2) | 0.106 (2) | |
H40 | 0.7658 | 0.5723 | 0.0551 | 0.127* | |
C41 | 0.8951 (11) | 0.6477 (5) | 0.0863 (3) | 0.122 (3) | |
H41 | 0.8614 | 0.6850 | 0.0631 | 0.147* | |
C42 | 1.0058 (9) | 0.6589 (4) | 0.1253 (3) | 0.108 (2) | |
H42 | 1.0509 | 0.7030 | 0.1264 | 0.130* | |
C43 | 1.0477 (6) | 0.6051 (3) | 0.1617 (2) | 0.0752 (14) | |
C44 | 1.1609 (7) | 0.6066 (4) | 0.2063 (3) | 0.0996 (19) | |
H44A | 1.1489 | 0.6469 | 0.2328 | 0.119* | |
H44B | 1.2520 | 0.6104 | 0.1874 | 0.119* | |
C45 | 1.1480 (5) | 0.5362 (3) | 0.2394 (2) | 0.0775 (14) | |
H45 | 1.2400 | 0.5134 | 0.2441 | 0.093* | |
C46 | 0.9387 (6) | 0.5240 (3) | 0.2877 (2) | 0.0717 (13) | |
H46A | 0.8829 | 0.5629 | 0.2717 | 0.086* | |
H46B | 0.8983 | 0.5096 | 0.3252 | 0.086* | |
N1 | 0.3745 (4) | 0.5660 (2) | 0.44453 (15) | 0.0666 (10) | |
N2 | 0.9409 (4) | 0.46430 (18) | 0.24736 (15) | 0.0602 (9) | |
O1 | 0.2617 (6) | 0.4581 (3) | 0.4267 (2) | 0.1235 (17) | |
O2 | 0.3587 (5) | 0.7026 (2) | 0.41557 (16) | 0.0988 (12) | |
H2 | 0.3666 | 0.6697 | 0.4393 | 0.148* | |
O3 | 1.0811 (4) | 0.5465 (2) | 0.29564 (14) | 0.0880 (11) | |
O4 | 0.6813 (4) | 0.4089 (3) | 0.2647 (2) | 0.1075 (14) | |
H4 | 0.7430 | 0.4245 | 0.2429 | 0.161* | |
Cl1 | 0.6075 (2) | 0.62902 (16) | 0.18796 (7) | 0.1484 (10) | |
Cl2 | 0.8897 (3) | 0.29449 (13) | 0.48823 (9) | 0.1505 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.052 (3) | 0.127 (5) | 0.068 (3) | −0.008 (3) | −0.015 (2) | 0.020 (4) |
C2 | 0.082 (4) | 0.123 (5) | 0.071 (3) | −0.015 (4) | −0.010 (3) | −0.002 (4) |
C3 | 0.097 (5) | 0.166 (7) | 0.071 (4) | 0.017 (5) | −0.006 (4) | −0.003 (4) |
C4 | 0.096 (5) | 0.195 (10) | 0.086 (5) | −0.005 (6) | −0.001 (4) | 0.025 (6) |
C5 | 0.082 (5) | 0.201 (9) | 0.115 (6) | −0.032 (6) | −0.021 (5) | 0.080 (6) |
C6 | 0.072 (4) | 0.115 (5) | 0.090 (4) | −0.013 (4) | −0.014 (3) | 0.020 (4) |
C7 | 0.111 (5) | 0.119 (6) | 0.134 (6) | −0.044 (5) | −0.047 (5) | 0.051 (5) |
C8 | 0.089 (4) | 0.096 (4) | 0.107 (4) | −0.008 (3) | −0.035 (4) | 0.005 (4) |
C9 | 0.054 (3) | 0.094 (4) | 0.074 (3) | 0.000 (3) | −0.017 (2) | 0.006 (3) |
C10 | 0.051 (3) | 0.185 (8) | 0.068 (3) | −0.014 (4) | −0.021 (2) | −0.004 (4) |
C11 | 0.049 (2) | 0.062 (3) | 0.070 (3) | 0.007 (2) | −0.017 (2) | −0.020 (2) |
C12 | 0.043 (2) | 0.074 (3) | 0.061 (2) | 0.005 (2) | −0.007 (2) | −0.015 (2) |
C13 | 0.060 (3) | 0.093 (4) | 0.065 (3) | 0.021 (3) | −0.008 (2) | 0.005 (3) |
C14 | 0.084 (4) | 0.109 (5) | 0.107 (5) | 0.020 (4) | −0.009 (4) | 0.010 (4) |
C15 | 0.083 (4) | 0.138 (6) | 0.080 (4) | −0.012 (4) | −0.012 (3) | 0.029 (4) |
C16 | 0.078 (4) | 0.131 (5) | 0.059 (3) | −0.020 (4) | 0.001 (3) | −0.012 (4) |
C17 | 0.054 (3) | 0.096 (4) | 0.064 (3) | −0.005 (2) | −0.006 (2) | −0.025 (3) |
C18 | 0.050 (2) | 0.072 (3) | 0.056 (2) | 0.005 (2) | −0.007 (2) | −0.010 (2) |
C19 | 0.045 (2) | 0.079 (3) | 0.085 (3) | 0.003 (2) | −0.008 (2) | −0.001 (3) |
C20 | 0.063 (3) | 0.099 (4) | 0.122 (5) | 0.017 (3) | −0.024 (3) | 0.009 (4) |
C21 | 0.057 (3) | 0.117 (5) | 0.090 (4) | −0.003 (3) | −0.024 (3) | 0.003 (4) |
C22 | 0.103 (5) | 0.094 (4) | 0.113 (5) | −0.021 (4) | −0.020 (4) | −0.021 (4) |
C23 | 0.065 (3) | 0.089 (4) | 0.115 (4) | 0.007 (3) | −0.031 (3) | −0.038 (4) |
C24 | 0.121 (5) | 0.120 (5) | 0.119 (6) | −0.020 (5) | 0.050 (5) | −0.051 (5) |
C25 | 0.170 (9) | 0.073 (4) | 0.116 (6) | −0.029 (4) | 0.061 (6) | −0.018 (4) |
C26 | 0.100 (5) | 0.089 (4) | 0.112 (5) | 0.005 (4) | 0.033 (4) | −0.003 (4) |
C27 | 0.110 (5) | 0.070 (3) | 0.096 (4) | 0.014 (3) | 0.026 (4) | 0.016 (3) |
C28 | 0.093 (4) | 0.066 (3) | 0.095 (4) | 0.006 (3) | 0.010 (3) | −0.007 (3) |
C29 | 0.092 (4) | 0.091 (4) | 0.089 (4) | −0.016 (3) | −0.016 (4) | −0.011 (3) |
C30 | 0.075 (3) | 0.067 (3) | 0.077 (3) | 0.009 (3) | 0.012 (3) | 0.009 (3) |
C31 | 0.065 (3) | 0.058 (3) | 0.079 (3) | 0.010 (2) | 0.015 (3) | 0.010 (2) |
C32 | 0.106 (4) | 0.088 (4) | 0.088 (4) | 0.021 (4) | 0.011 (4) | 0.006 (3) |
C33 | 0.101 (5) | 0.078 (4) | 0.152 (6) | 0.041 (4) | 0.016 (5) | −0.006 (4) |
C34 | 0.113 (5) | 0.069 (4) | 0.120 (5) | 0.005 (4) | 0.036 (4) | −0.007 (4) |
C35 | 0.085 (4) | 0.084 (4) | 0.120 (5) | 0.004 (3) | 0.014 (3) | −0.028 (4) |
C36 | 0.064 (3) | 0.077 (4) | 0.124 (5) | 0.015 (3) | 0.009 (3) | −0.015 (3) |
C37 | 0.054 (2) | 0.062 (3) | 0.061 (3) | 0.003 (2) | −0.006 (2) | −0.004 (2) |
C38 | 0.068 (3) | 0.072 (3) | 0.046 (2) | 0.001 (3) | 0.008 (2) | −0.004 (2) |
C39 | 0.086 (3) | 0.095 (4) | 0.050 (2) | 0.011 (3) | 0.001 (3) | −0.010 (3) |
C40 | 0.096 (4) | 0.177 (7) | 0.044 (3) | 0.058 (5) | −0.007 (3) | −0.006 (4) |
C41 | 0.180 (8) | 0.109 (6) | 0.078 (4) | 0.042 (6) | 0.026 (5) | 0.014 (4) |
C42 | 0.147 (7) | 0.090 (4) | 0.088 (4) | 0.001 (5) | 0.039 (5) | 0.017 (4) |
C43 | 0.091 (4) | 0.077 (3) | 0.058 (3) | −0.007 (3) | 0.010 (3) | 0.008 (3) |
C44 | 0.094 (4) | 0.108 (4) | 0.097 (4) | −0.037 (4) | 0.011 (3) | −0.013 (4) |
C45 | 0.061 (3) | 0.093 (4) | 0.079 (3) | −0.006 (3) | −0.014 (3) | −0.001 (3) |
C46 | 0.091 (4) | 0.069 (3) | 0.055 (2) | 0.000 (3) | 0.005 (2) | −0.006 (2) |
N1 | 0.0445 (19) | 0.098 (3) | 0.057 (2) | 0.001 (2) | −0.0093 (17) | −0.002 (2) |
N2 | 0.066 (2) | 0.0515 (19) | 0.063 (2) | 0.0046 (17) | 0.0071 (18) | 0.0015 (18) |
O1 | 0.140 (4) | 0.123 (4) | 0.108 (3) | −0.058 (3) | −0.047 (3) | 0.011 (3) |
O2 | 0.109 (3) | 0.105 (3) | 0.082 (2) | 0.049 (2) | 0.010 (2) | −0.014 (2) |
O3 | 0.103 (3) | 0.105 (3) | 0.0558 (18) | −0.015 (2) | −0.0176 (18) | −0.0075 (18) |
O4 | 0.058 (2) | 0.131 (3) | 0.133 (4) | −0.004 (2) | 0.017 (2) | −0.043 (3) |
Cl1 | 0.1316 (16) | 0.244 (3) | 0.0694 (9) | −0.0521 (17) | 0.0276 (10) | −0.0383 (12) |
Cl2 | 0.205 (2) | 0.1392 (16) | 0.1069 (12) | 0.0437 (16) | 0.0530 (15) | 0.0297 (12) |
Geometric parameters (Å, º) top
C1—C6 | 1.374 (8) | C24—C29 | 1.482 (9) |
C1—C2 | 1.386 (9) | C24—H24 | 0.9300 |
C1—C9 | 1.509 (8) | C25—C26 | 1.357 (11) |
C2—C3 | 1.380 (9) | C25—H25 | 0.9300 |
C2—H2A | 0.9300 | C26—C27 | 1.351 (9) |
C3—C4 | 1.319 (11) | C26—Cl2 | 1.722 (8) |
C3—H3 | 0.9300 | C27—C28 | 1.371 (8) |
C4—C5 | 1.448 (12) | C27—H27 | 0.9300 |
C4—H4A | 0.9300 | C28—C29 | 1.342 (9) |
C5—C6 | 1.397 (11) | C28—C30 | 1.500 (8) |
C5—H5 | 0.9300 | C29—O4 | 1.375 (7) |
C6—C7 | 1.428 (10) | C30—C31 | 1.507 (7) |
C7—C8 | 1.547 (10) | C30—N2 | 1.515 (6) |
C7—H7A | 0.9700 | C30—H30 | 0.9800 |
C7—H7B | 0.9700 | C31—C32 | 1.360 (8) |
C8—O1 | 1.431 (7) | C31—C36 | 1.390 (8) |
C8—C9 | 1.510 (8) | C32—C33 | 1.380 (9) |
C8—H8 | 0.9800 | C32—H32 | 0.9300 |
C9—N1 | 1.471 (6) | C33—C34 | 1.371 (10) |
C9—H9 | 0.9800 | C33—H33 | 0.9300 |
C10—O1 | 1.411 (9) | C34—C35 | 1.368 (9) |
C10—N1 | 1.486 (6) | C34—H34 | 0.9300 |
C10—H10A | 0.9700 | C35—C36 | 1.372 (8) |
C10—H10B | 0.9700 | C35—H35 | 0.9300 |
C11—N1 | 1.494 (6) | C36—H36 | 0.9300 |
C11—C18 | 1.495 (6) | C37—N2 | 1.481 (6) |
C11—C12 | 1.510 (6) | C37—C38 | 1.505 (6) |
C11—H11 | 0.9800 | C37—C45 | 1.529 (6) |
C12—C17 | 1.373 (6) | C37—H37 | 0.9800 |
C12—C13 | 1.389 (7) | C38—C39 | 1.375 (7) |
C13—O2 | 1.363 (6) | C38—C43 | 1.387 (7) |
C13—C14 | 1.376 (8) | C39—C40 | 1.398 (9) |
C14—C15 | 1.375 (9) | C39—H39 | 0.9300 |
C14—H14 | 0.9300 | C40—C41 | 1.372 (11) |
C15—C16 | 1.373 (10) | C40—H40 | 0.9300 |
C15—H15 | 0.9300 | C41—C42 | 1.392 (11) |
C16—C17 | 1.333 (8) | C41—H41 | 0.9300 |
C16—Cl1 | 1.742 (6) | C42—C43 | 1.359 (8) |
C17—H17 | 0.9300 | C42—H42 | 0.9300 |
C18—C23 | 1.362 (6) | C43—C44 | 1.478 (8) |
C18—C19 | 1.397 (6) | C44—C45 | 1.518 (9) |
C19—C20 | 1.397 (7) | C44—H44A | 0.9700 |
C19—H19 | 0.9300 | C44—H44B | 0.9700 |
C20—C21 | 1.318 (8) | C45—O3 | 1.439 (6) |
C20—H20 | 0.9300 | C45—H45 | 0.9800 |
C21—C22 | 1.367 (9) | C46—O3 | 1.432 (6) |
C21—H21 | 0.9300 | C46—N2 | 1.442 (6) |
C22—C23 | 1.407 (8) | C46—H46A | 0.9700 |
C22—H22 | 0.9300 | C46—H46B | 0.9700 |
C23—H23 | 0.9300 | O2—H2 | 0.8200 |
C24—C25 | 1.386 (11) | O4—H4 | 0.8200 |
| | | |
C6—C1—C2 | 121.8 (6) | C24—C25—H25 | 118.5 |
C6—C1—C9 | 109.5 (6) | C27—C26—C25 | 118.2 (7) |
C2—C1—C9 | 128.7 (5) | C27—C26—Cl2 | 122.2 (6) |
C3—C2—C1 | 119.4 (7) | C25—C26—Cl2 | 119.4 (6) |
C3—C2—H2A | 120.3 | C26—C27—C28 | 124.4 (7) |
C1—C2—H2A | 120.3 | C26—C27—H27 | 117.8 |
C4—C3—C2 | 121.3 (8) | C28—C27—H27 | 117.8 |
C4—C3—H3 | 119.4 | C29—C28—C27 | 117.8 (6) |
C2—C3—H3 | 119.4 | C29—C28—C30 | 120.4 (6) |
C3—C4—C5 | 120.5 (8) | C27—C28—C30 | 121.6 (6) |
C3—C4—H4A | 119.7 | C28—C29—O4 | 125.7 (6) |
C5—C4—H4A | 119.7 | C28—C29—C24 | 121.3 (7) |
C6—C5—C4 | 118.5 (7) | O4—C29—C24 | 112.9 (6) |
C6—C5—H5 | 120.8 | C28—C30—C31 | 112.0 (4) |
C4—C5—H5 | 120.8 | C28—C30—N2 | 110.8 (4) |
C1—C6—C5 | 118.6 (8) | C31—C30—N2 | 111.4 (4) |
C1—C6—C7 | 112.6 (6) | C28—C30—H30 | 107.5 |
C5—C6—C7 | 128.9 (8) | C31—C30—H30 | 107.5 |
C6—C7—C8 | 106.0 (5) | N2—C30—H30 | 107.5 |
C6—C7—H7A | 110.5 | C32—C31—C36 | 116.7 (5) |
C8—C7—H7A | 110.5 | C32—C31—C30 | 119.1 (5) |
C6—C7—H7B | 110.5 | C36—C31—C30 | 124.1 (4) |
C8—C7—H7B | 110.5 | C31—C32—C33 | 121.8 (6) |
H7A—C7—H7B | 108.7 | C31—C32—H32 | 119.1 |
O1—C8—C9 | 104.3 (5) | C33—C32—H32 | 119.1 |
O1—C8—C7 | 113.3 (5) | C34—C33—C32 | 119.9 (6) |
C9—C8—C7 | 105.2 (6) | C34—C33—H33 | 120.1 |
O1—C8—H8 | 111.2 | C32—C33—H33 | 120.1 |
C9—C8—H8 | 111.2 | C35—C34—C33 | 120.1 (6) |
C7—C8—H8 | 111.2 | C35—C34—H34 | 120.0 |
N1—C9—C1 | 112.8 (4) | C33—C34—H34 | 120.0 |
N1—C9—C8 | 107.2 (4) | C34—C35—C36 | 118.7 (7) |
C1—C9—C8 | 105.2 (5) | C34—C35—H35 | 120.7 |
N1—C9—H9 | 110.5 | C36—C35—H35 | 120.7 |
C1—C9—H9 | 110.5 | C35—C36—C31 | 122.8 (6) |
C8—C9—H9 | 110.5 | C35—C36—H36 | 118.6 |
O1—C10—N1 | 106.2 (5) | C31—C36—H36 | 118.6 |
O1—C10—H10A | 110.5 | N2—C37—C38 | 111.6 (4) |
N1—C10—H10A | 110.5 | N2—C37—C45 | 105.3 (3) |
O1—C10—H10B | 110.5 | C38—C37—C45 | 103.9 (4) |
N1—C10—H10B | 110.5 | N2—C37—H37 | 111.9 |
H10A—C10—H10B | 108.7 | C38—C37—H37 | 111.9 |
N1—C11—C18 | 111.5 (3) | C45—C37—H37 | 111.9 |
N1—C11—C12 | 109.7 (3) | C39—C38—C43 | 120.0 (5) |
C18—C11—C12 | 112.1 (4) | C39—C38—C37 | 128.8 (4) |
N1—C11—H11 | 107.8 | C43—C38—C37 | 111.1 (4) |
C18—C11—H11 | 107.8 | C38—C39—C40 | 118.4 (6) |
C12—C11—H11 | 107.8 | C38—C39—H39 | 120.8 |
C17—C12—C13 | 117.6 (5) | C40—C39—H39 | 120.8 |
C17—C12—C11 | 120.4 (4) | C41—C40—C39 | 121.4 (6) |
C13—C12—C11 | 121.7 (4) | C41—C40—H40 | 119.3 |
O2—C13—C14 | 117.5 (5) | C39—C40—H40 | 119.3 |
O2—C13—C12 | 122.6 (4) | C40—C41—C42 | 119.0 (7) |
C14—C13—C12 | 119.9 (5) | C40—C41—H41 | 120.5 |
C15—C14—C13 | 120.5 (6) | C42—C41—H41 | 120.5 |
C15—C14—H14 | 119.8 | C43—C42—C41 | 119.9 (7) |
C13—C14—H14 | 119.8 | C43—C42—H42 | 120.1 |
C16—C15—C14 | 119.1 (6) | C41—C42—H42 | 120.1 |
C16—C15—H15 | 120.5 | C42—C43—C38 | 121.1 (6) |
C14—C15—H15 | 120.5 | C42—C43—C44 | 128.0 (6) |
C17—C16—C15 | 120.1 (5) | C38—C43—C44 | 110.8 (5) |
C17—C16—Cl1 | 120.8 (6) | C43—C44—C45 | 105.3 (4) |
C15—C16—Cl1 | 119.0 (6) | C43—C44—H44A | 110.7 |
C16—C17—C12 | 122.8 (5) | C45—C44—H44A | 110.7 |
C16—C17—H17 | 118.6 | C43—C44—H44B | 110.7 |
C12—C17—H17 | 118.6 | C45—C44—H44B | 110.7 |
C23—C18—C19 | 117.8 (4) | H44A—C44—H44B | 108.8 |
C23—C18—C11 | 122.7 (4) | O3—C45—C44 | 111.1 (5) |
C19—C18—C11 | 119.4 (4) | O3—C45—C37 | 105.2 (4) |
C18—C19—C20 | 119.8 (5) | C44—C45—C37 | 107.4 (4) |
C18—C19—H19 | 120.1 | O3—C45—H45 | 111.0 |
C20—C19—H19 | 120.1 | C44—C45—H45 | 111.0 |
C21—C20—C19 | 122.7 (5) | C37—C45—H45 | 111.0 |
C21—C20—H20 | 118.7 | O3—C46—N2 | 107.0 (4) |
C19—C20—H20 | 118.7 | O3—C46—H46A | 110.3 |
C20—C21—C22 | 118.3 (5) | N2—C46—H46A | 110.3 |
C20—C21—H21 | 120.9 | O3—C46—H46B | 110.3 |
C22—C21—H21 | 120.9 | N2—C46—H46B | 110.3 |
C21—C22—C23 | 121.4 (6) | H46A—C46—H46B | 108.6 |
C21—C22—H22 | 119.3 | C9—N1—C10 | 99.2 (4) |
C23—C22—H22 | 119.3 | C9—N1—C11 | 116.6 (3) |
C18—C23—C22 | 120.1 (5) | C10—N1—C11 | 111.8 (3) |
C18—C23—H23 | 119.9 | C46—N2—C37 | 101.2 (3) |
C22—C23—H23 | 120.0 | C46—N2—C30 | 110.6 (3) |
C25—C24—C29 | 115.0 (7) | C37—N2—C30 | 112.1 (3) |
C25—C24—H24 | 122.5 | C10—O1—C8 | 107.3 (4) |
C29—C24—H24 | 122.5 | C13—O2—H2 | 109.5 |
C26—C25—C24 | 123.0 (7) | C46—O3—C45 | 105.7 (3) |
C26—C25—H25 | 118.5 | C29—O4—H4 | 109.5 |
| | | |
C6—C1—C2—C3 | 0.6 (8) | C29—C28—C30—C31 | −80.1 (6) |
C9—C1—C2—C3 | 179.7 (5) | C27—C28—C30—C31 | 95.1 (6) |
C1—C2—C3—C4 | 0.4 (9) | C29—C28—C30—N2 | 44.9 (7) |
C2—C3—C4—C5 | −1.3 (11) | C27—C28—C30—N2 | −139.9 (5) |
C3—C4—C5—C6 | 1.2 (11) | C28—C30—C31—C32 | −89.9 (6) |
C2—C1—C6—C5 | −0.7 (8) | N2—C30—C31—C32 | 145.5 (5) |
C9—C1—C6—C5 | −179.9 (5) | C28—C30—C31—C36 | 87.5 (6) |
C2—C1—C6—C7 | 179.5 (5) | N2—C30—C31—C36 | −37.2 (7) |
C9—C1—C6—C7 | 0.3 (7) | C36—C31—C32—C33 | 1.4 (9) |
C4—C5—C6—C1 | −0.2 (9) | C30—C31—C32—C33 | 178.9 (5) |
C4—C5—C6—C7 | 179.6 (7) | C31—C32—C33—C34 | −2.4 (10) |
C1—C6—C7—C8 | −7.8 (7) | C32—C33—C34—C35 | 1.4 (10) |
C5—C6—C7—C8 | 172.5 (6) | C33—C34—C35—C36 | 0.4 (10) |
C6—C7—C8—O1 | −101.5 (6) | C34—C35—C36—C31 | −1.4 (9) |
C6—C7—C8—C9 | 11.9 (6) | C32—C31—C36—C35 | 0.5 (8) |
C6—C1—C9—N1 | 123.9 (5) | C30—C31—C36—C35 | −176.8 (5) |
C2—C1—C9—N1 | −55.3 (7) | N2—C37—C38—C39 | −60.6 (6) |
C6—C1—C9—C8 | 7.5 (5) | C45—C37—C38—C39 | −173.6 (5) |
C2—C1—C9—C8 | −171.7 (5) | N2—C37—C38—C43 | 117.6 (4) |
O1—C8—C9—N1 | −12.2 (6) | C45—C37—C38—C43 | 4.6 (5) |
C7—C8—C9—N1 | −131.8 (5) | C43—C38—C39—C40 | −0.9 (7) |
O1—C8—C9—C1 | 108.0 (5) | C37—C38—C39—C40 | 177.2 (4) |
C7—C8—C9—C1 | −11.6 (5) | C38—C39—C40—C41 | −0.6 (8) |
N1—C11—C12—C17 | −147.1 (4) | C39—C40—C41—C42 | 3.3 (10) |
C18—C11—C12—C17 | 88.4 (5) | C40—C41—C42—C43 | −4.4 (10) |
N1—C11—C12—C13 | 39.1 (5) | C41—C42—C43—C38 | 3.0 (9) |
C18—C11—C12—C13 | −85.4 (5) | C41—C42—C43—C44 | −179.2 (6) |
C17—C12—C13—O2 | 179.5 (5) | C39—C38—C43—C42 | −0.3 (7) |
C11—C12—C13—O2 | −6.6 (7) | C37—C38—C43—C42 | −178.7 (5) |
C17—C12—C13—C14 | −0.5 (7) | C39—C38—C43—C44 | −178.4 (5) |
C11—C12—C13—C14 | 173.4 (5) | C37—C38—C43—C44 | 3.2 (6) |
O2—C13—C14—C15 | −179.7 (6) | C42—C43—C44—C45 | 172.3 (6) |
C12—C13—C14—C15 | 0.2 (9) | C38—C43—C44—C45 | −9.7 (6) |
C13—C14—C15—C16 | 0.2 (10) | C43—C44—C45—O3 | −102.2 (5) |
C14—C15—C16—C17 | −0.3 (9) | C43—C44—C45—C37 | 12.3 (6) |
C14—C15—C16—Cl1 | −177.4 (5) | N2—C37—C45—O3 | −9.4 (5) |
C15—C16—C17—C12 | 0.0 (8) | C38—C37—C45—O3 | 108.0 (4) |
Cl1—C16—C17—C12 | 177.1 (4) | N2—C37—C45—C44 | −127.8 (4) |
C13—C12—C17—C16 | 0.4 (7) | C38—C37—C45—C44 | −10.4 (5) |
C11—C12—C17—C16 | −173.6 (4) | C1—C9—N1—C10 | −84.4 (5) |
N1—C11—C18—C23 | −63.3 (6) | C8—C9—N1—C10 | 30.9 (5) |
C12—C11—C18—C23 | 60.1 (6) | C1—C9—N1—C11 | 155.5 (4) |
N1—C11—C18—C19 | 119.1 (4) | C8—C9—N1—C11 | −89.2 (5) |
C12—C11—C18—C19 | −117.5 (5) | O1—C10—N1—C9 | −39.9 (5) |
C23—C18—C19—C20 | 0.3 (8) | O1—C10—N1—C11 | 83.7 (5) |
C11—C18—C19—C20 | 178.0 (5) | C18—C11—N1—C9 | −50.5 (5) |
C18—C19—C20—C21 | 0.2 (9) | C12—C11—N1—C9 | −175.4 (4) |
C19—C20—C21—C22 | 0.5 (10) | C18—C11—N1—C10 | −163.7 (5) |
C20—C21—C22—C23 | −1.6 (10) | C12—C11—N1—C10 | 71.5 (5) |
C19—C18—C23—C22 | −1.4 (8) | O3—C46—N2—C37 | −40.2 (4) |
C11—C18—C23—C22 | −179.0 (5) | O3—C46—N2—C30 | 78.7 (5) |
C21—C22—C23—C18 | 2.1 (10) | C38—C37—N2—C46 | −82.6 (4) |
C29—C24—C25—C26 | 4.9 (10) | C45—C37—N2—C46 | 29.4 (4) |
C24—C25—C26—C27 | −7.4 (10) | C38—C37—N2—C30 | 159.5 (4) |
C24—C25—C26—Cl2 | 178.7 (5) | C45—C37—N2—C30 | −88.4 (4) |
C25—C26—C27—C28 | 5.0 (10) | C28—C30—N2—C46 | 63.1 (5) |
Cl2—C26—C27—C28 | 178.7 (5) | C31—C30—N2—C46 | −171.6 (4) |
C26—C27—C28—C29 | −0.2 (9) | C28—C30—N2—C37 | 175.3 (4) |
C26—C27—C28—C30 | −175.6 (5) | C31—C30—N2—C37 | −59.4 (5) |
C27—C28—C29—O4 | 174.7 (5) | N1—C10—O1—C8 | 34.3 (6) |
C30—C28—C29—O4 | −9.8 (9) | C9—C8—O1—C10 | −13.4 (7) |
C27—C28—C29—C24 | −2.3 (9) | C7—C8—O1—C10 | 100.5 (7) |
C30—C28—C29—C24 | 173.1 (5) | N2—C46—O3—C45 | 35.3 (5) |
C25—C24—C29—C28 | 0.1 (9) | C44—C45—O3—C46 | 101.0 (5) |
C25—C24—C29—O4 | −177.3 (5) | C37—C45—O3—C46 | −14.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.82 | 1.94 | 2.636 (5) | 142 |
O4—H4···N2 | 0.82 | 2.03 | 2.709 (6) | 140 |